data_m25107 
 
_audit_creation_method            'SHELXL-2019/3 and CIFFIX' 
# CIF edited on-the-fly by script CIFFIX (S. Parkin, 2000-2025). 
# CIFFIX: https://xray.uky.edu/Resources/scripts/ciffix 
_audit_update_record              ? 
 
_shelx_SHELXL_version_number      '2019/3' 
 
_publ_section_exptl_refinement 
; 
H atoms were found in difference Fourier maps, but subsequently included 
in the refinement using riding models, with constrained distances set to 
0.95 Å (Cₛₚ₂H), 0.98 Å (RCH₃), 0.99 Å (R₂CH₂) and 1.00 Å 
(R₃CH).  Uiso(H) parameters were set to values of either 1.2Ueq or 
1.5Ueq (RCH₃ only) of the attached atom. 
; 
 
_publ_section_references 
; 
Bruker-AXS (2023). 
  APEX5 Bruker-AXS Inc., Madison, WI, USA. 
 
Hope, H. (1994). 
  Prog. Inorg. Chem. 41, 1--19. 
 
Krause, L., Herbst-Irmer, R., Sheldrick, G.M. & Stalke, D. (2015). 
  J. Appl. Cryst. 48, 3--10. 
 
Parkin, S. & Hope, H. (1998). 
  J. Appl. Cryst. 31, 945--953. 
 
Parkin, S. (2000). 
  Acta Cryst. A56, 157--162. 
 
Parkin, S. (2013). 
  CIFFIX, https://xray.uky.edu/Resources/scripts/ciffix 
 
Sheldrick, G.M. (2008). 
  Acta Cryst. A64, 112--122. 
 
Sheldrick, G.M. (2015a). 
  Acta Cryst. A71, 3--8. 
 
Sheldrick, G.M. (2015b). 
  Acta Cryst. C71, 3--8. 
 
Spek, A.L. (2020). 
  Acta Cryst. E76, 1--11. 
 
Westrip, S.P. (2010). 
  J. Appl. Cryst. 43, 920--925. 
; 
 
_publ_section_acknowledgements 
; 
The D8 Venture diffractometer was funded by the NSF (MRI CHE1625732), 
and by the University of Kentucky. 
; 
 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          'C17 H22 Cl N3 O' 
_chemical_formula_sum             'C17 H22 Cl N3 O' 
_chemical_formula_weight          319.82 
 
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0033   0.0016 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'Cl'  'Cl'   0.1484   0.1585 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'N'  'N'   0.0061   0.0033 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0106   0.0060 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 
_space_group_crystal_system       monoclinic 
_space_group_IT_number            14 
_space_group_name_H-M_alt         'P 21/c' 
_space_group_name_Hall            '-P 2ybc' 
 
_shelx_space_group_comment 
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
; 
 
loop_ 
 _space_group_symop_operation_xyz 
 'x, y, z' 
 '-x, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x, -y-1/2, z-1/2' 
 
_cell_length_a                    21.1989(6) 
_cell_length_b                    9.5096(3) 
_cell_length_c                    17.6330(5) 
_cell_angle_alpha                 90 
_cell_angle_beta                  110.483(1) 
_cell_angle_gamma                 90 
_cell_volume                      3329.95(17) 
_cell_formula_units_Z             8 
_cell_measurement_temperature     100.0(2) 
_cell_measurement_reflns_used     9892 
_cell_measurement_theta_min       2.84 
_cell_measurement_theta_max       27.53 
 
_exptl_crystal_description        slab 
_exptl_crystal_colour             colourless 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.276 
_exptl_crystal_F_000              1360 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.220 
_exptl_crystal_size_mid           0.200 
_exptl_crystal_size_min           0.110 
_exptl_absorpt_coefficient_mu     0.235 
_shelx_estimated_absorpt_T_min    0.950 
_shelx_estimated_absorpt_T_max    0.975 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.903 
_exptl_absorpt_correction_T_max   0.971 
_exptl_absorpt_process_details    'SADABS (Krause et al., 2015)' 
_exptl_absorpt_special_details 
; 
In addition to absorption, multi-scan techniques also correct other slowly 
varying changes in scale factor over reciprocal space, such as those caused 
by X-ray beam inhomogeneity, goniometer imperfection, crystal decomposition, 
crystal longer than the X-ray beam cross section, absorption by the crystal 
mount, scan truncation etc. These account, by and large, for the difference 
between SHELX estimates of Tmin and Tmax and the _exptl_absorpt_correction_ 
values. 
; 
 
_exptl_special_details 
; 
The crystal was mounted using polyisobutene oil on the tip of a fine glass 
fibre, which was fastened in a copper mounting pin with electrical solder. 
It was placed directly into the cold gas stream of a liquid-nitrogen based 
cryostat (Hope, 1994; Parkin & Hope, 1998). 
 
Diffraction data were collected with the crystal at 100K. 
; 
 
_diffrn_ambient_temperature       100.0(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_source                    'microsource' 
_diffrn_measurement_device_type   'Bruker D8 Venture dual source' 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  7.41 
_diffrn_reflns_number             60403 
_diffrn_reflns_av_unetI/netI      0.0252 
_diffrn_reflns_av_R_equivalents   0.0399 
_diffrn_reflns_limit_h_min        -27 
_diffrn_reflns_limit_h_max        25 
_diffrn_reflns_limit_k_min        -12 
_diffrn_reflns_limit_k_max        12 
_diffrn_reflns_limit_l_min        -22 
_diffrn_reflns_limit_l_max        22 
_diffrn_reflns_theta_min          2.051 
_diffrn_reflns_theta_max          27.558 
_diffrn_reflns_theta_full         25.242 
_diffrn_measured_fraction_theta_max                0.996 
_diffrn_measured_fraction_theta_full               0.999 
_diffrn_reflns_Laue_measured_fraction_max          0.996 
_diffrn_reflns_Laue_measured_fraction_full         0.999 
_diffrn_reflns_point_group_measured_fraction_max   0.996 
_diffrn_reflns_point_group_measured_fraction_full  0.999 
 
_reflns_number_total              7671 
_reflns_number_gt                 6719 
_reflns_threshold_expression      'I > 2σ(I)' 
_reflns_Friedel_coverage          0.000 
_reflns_Friedel_fraction_max      . 
_reflns_Friedel_fraction_full     . 
_reflns_special_details 
; 
Reflections were merged by SHELXL according to the crystal 
class for the calculation of statistics and refinement. 
 
_reflns_Friedel_fraction is defined as the number of unique 
Friedel pairs measured divided by the number that would be 
possible theoretically, ignoring centric projections and 
systematic absences. 
; 
 
_computing_data_collection        'APEX5 (Bruker-AXS, 2023)' 
_computing_cell_refinement        'APEX5 (Bruker-AXS, 2023)' 
_computing_data_reduction         'APEX5 (Bruker-AXS, 2023)' 
_computing_structure_solution     'SHELXT (Sheldrick, 2015a)' 
_computing_structure_refinement   'SHELXL-2019/3 (Sheldrick, 2015b)' 
_computing_molecular_graphics     'XP in SHELXTL (Sheldrick, 2008)' 
_computing_publication_material 
'SHELX (Sheldrick, 2008) and CIFFIX (Parkin, 2013)' 
 
_refine_special_details 
; 
Refinement progress was checked using Platon (Spek, 2020) and by 
an R-tensor (Parkin, 2000). The final model was further checked 
with the IUCr utility checkCIF. 
; 
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
'w=1/[σ²(Fo²)+(0.0277P)²+2.5386P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    difmap 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      'SHELXL-2019/2 (Sheldrick 2019)' 
_refine_ls_extinction_coef        0.0014(3) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_number_reflns          7671 
_refine_ls_number_parameters      406 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0450 
_refine_ls_R_factor_gt            0.0381 
_refine_ls_wR_factor_ref          0.1002 
_refine_ls_wR_factor_gt           0.0964 
_refine_ls_goodness_of_fit_ref    1.147 
_refine_ls_restrained_S_all       1.147 
_refine_ls_shift/su_max           0.001 
_refine_ls_shift/su_mean          0.000 
 
loop_ 
 _atom_site_label 
 _atom_site_type_symbol 
 _atom_site_fract_x 
 _atom_site_fract_y 
 _atom_site_fract_z 
 _atom_site_U_iso_or_equiv 
 _atom_site_adp_type 
 _atom_site_occupancy 
 _atom_site_site_symmetry_order 
 _atom_site_calc_flag 
 _atom_site_refinement_flags_posn 
 _atom_site_refinement_flags_adp 
 _atom_site_refinement_flags_occupancy 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
Cl1A Cl 0.68175(2) 0.71920(4) 0.40138(2) 0.02457(10) Uani 1 1 d . . . . . 
O1A O 0.52795(5) 0.05539(12) 0.62641(7) 0.0196(2) Uani 1 1 d . . . . . 
H1A H 0.5127(4) -0.008(2) 0.6496(11) 0.029 Uiso 1 1 calc R U . . . 
N1A N 0.60358(7) 0.20248(14) 0.77571(8) 0.0195(3) Uani 1 1 d . . . . . 
N2A N 0.64966(7) 0.30544(16) 0.80922(9) 0.0277(3) Uani 1 1 d . . . . . 
N3A N 0.54519(7) 0.37624(15) 0.79895(9) 0.0252(3) Uani 1 1 d . . . . . 
C1A C 0.62454(8) 0.07077(17) 0.74931(9) 0.0207(3) Uani 1 1 d . . . . . 
H1AA H 0.607522 -0.008482 0.773112 0.025 Uiso 1 1 calc R U . . . 
H1AB H 0.674336 0.066043 0.770581 0.025 Uiso 1 1 calc R U . . . 
C2A C 0.61194(9) 0.40646(19) 0.82161(11) 0.0285(4) Uani 1 1 d . . . . . 
H2A H 0.630073 0.494312 0.844747 0.034 Uiso 1 1 calc R U . . . 
C3A C 0.54260(8) 0.24617(18) 0.77086(10) 0.0223(3) Uani 1 1 d . . . . . 
H3A H 0.502680 0.191605 0.750096 0.027 Uiso 1 1 calc R U . . . 
C4A C 0.59973(7) 0.05243(16) 0.65730(9) 0.0172(3) Uani 1 1 d . . . . . 
C5A C 0.62298(8) 0.16560(16) 0.61033(9) 0.0185(3) Uani 1 1 d . . . . . 
H5A H 0.671963 0.183740 0.639758 0.022 Uiso 1 1 calc R U . . . 
C6A C 0.61530(9) 0.09397(18) 0.52911(10) 0.0234(3) Uani 1 1 d . . . . . 
H6AA H 0.573718 0.126703 0.486173 0.028 Uiso 1 1 calc R U . . . 
H6AB H 0.654268 0.116655 0.512683 0.028 Uiso 1 1 calc R U . . . 
C7A C 0.61181(10) -0.06495(18) 0.54219(10) 0.0268(4) Uani 1 1 d . . . . . 
H7AA H 0.645341 -0.114896 0.524671 0.032 Uiso 1 1 calc R U . . . 
H7AB H 0.566442 -0.101316 0.510573 0.032 Uiso 1 1 calc R U . . . 
C8A C 0.62713(8) -0.08738(16) 0.63359(10) 0.0197(3) Uani 1 1 d . . . . . 
C9A C 0.59222(9) -0.21937(17) 0.64933(11) 0.0254(3) Uani 1 1 d . . . . . 
H9AA H 0.543382 -0.209774 0.622694 0.038 Uiso 1 1 calc R U . . . 
H9AB H 0.603015 -0.231026 0.707740 0.038 Uiso 1 1 calc R U . . . 
H9AC H 0.607908 -0.301802 0.627642 0.038 Uiso 1 1 calc R U . . . 
C10A C 0.70333(8) -0.10486(18) 0.67767(11) 0.0249(3) Uani 1 1 d . . . . . 
H10D H 0.719344 -0.186311 0.655534 0.037 Uiso 1 1 calc R U . . . 
H10E H 0.712545 -0.119355 0.735586 0.037 Uiso 1 1 calc R U . . . 
H10F H 0.726673 -0.020057 0.670003 0.037 Uiso 1 1 calc R U . . . 
C11A C 0.58581(9) 0.30658(17) 0.59845(10) 0.0230(3) Uani 1 1 d . . . . . 
H11C H 0.536953 0.290105 0.571100 0.028 Uiso 1 1 calc R U . . . 
H11D H 0.592595 0.348816 0.652054 0.028 Uiso 1 1 calc R U . . . 
C12A C 0.61005(8) 0.40847(16) 0.54868(10) 0.0198(3) Uani 1 1 d . . . . . 
C13A C 0.56811(8) 0.45113(17) 0.47216(10) 0.0207(3) Uani 1 1 d . . . . . 
H13A H 0.523805 0.413879 0.450445 0.025 Uiso 1 1 calc R U . . . 
C14A C 0.58951(8) 0.54694(17) 0.42676(10) 0.0213(3) Uani 1 1 d . . . . . 
H14A H 0.560076 0.575885 0.374879 0.026 Uiso 1 1 calc R U . . . 
C15A C 0.65406(8) 0.59929(16) 0.45817(9) 0.0196(3) Uani 1 1 d . . . . . 
C16A C 0.69756(8) 0.55970(17) 0.53428(10) 0.0215(3) Uani 1 1 d . . . . . 
H16A H 0.741887 0.596966 0.555497 0.026 Uiso 1 1 calc R U . . . 
C17A C 0.67496(8) 0.46467(17) 0.57866(10) 0.0221(3) Uani 1 1 d . . . . . 
H17A H 0.704390 0.437069 0.630823 0.027 Uiso 1 1 calc R U . . . 
Cl1B Cl 0.81854(2) 0.26865(4) 0.24588(2) 0.02863(11) Uani 1 1 d . . . . . 
O1B O 0.96960(5) 0.92837(12) 0.60315(7) 0.0201(2) Uani 1 1 d . . . . . 
H1B H 0.9829(3) 0.993(2) 0.6401(13) 0.030 Uiso 1 1 calc R U . . . 
N1B N 0.89595(7) 0.76902(14) 0.68325(8) 0.0192(3) Uani 1 1 d . . . . . 
N2B N 0.85737(7) 0.65081(16) 0.66925(9) 0.0288(3) Uani 1 1 d . . . . . 
N3B N 0.96104(7) 0.60789(15) 0.76048(9) 0.0252(3) Uani 1 1 d . . . . . 
C1B C 0.87017(8) 0.89825(17) 0.63853(9) 0.0198(3) Uani 1 1 d . . . . . 
H1BA H 0.881943 0.978517 0.676690 0.024 Uiso 1 1 calc R U . . . 
H1BB H 0.820441 0.892691 0.614957 0.024 Uiso 1 1 calc R U . . . 
C2B C 0.89867(9) 0.55898(19) 0.71736(11) 0.0308(4) Uani 1 1 d . . . . . 
H2B H 0.885667 0.464548 0.721624 0.037 Uiso 1 1 calc R U . . . 
C3B C 0.95680(8) 0.74128(17) 0.73703(9) 0.0214(3) Uani 1 1 d . . . . . 
H3B H 0.992286 0.807857 0.755978 0.026 Uiso 1 1 calc R U . . . 
C4B C 0.89788(7) 0.92607(16) 0.57054(9) 0.0170(3) Uani 1 1 d . . . . . 
C5B C 0.87770(8) 0.81331(16) 0.50303(9) 0.0192(3) Uani 1 1 d . . . . . 
H5B H 0.831491 0.779048 0.496496 0.023 Uiso 1 1 calc R U . . . 
C6B C 0.87378(10) 0.89232(19) 0.4246(1) 0.0302(4) Uani 1 1 d . . . . . 
H6BA H 0.908484 0.856557 0.403812 0.036 Uiso 1 1 calc R U . . . 
H6BB H 0.828929 0.879158 0.382263 0.036 Uiso 1 1 calc R U . . . 
C7B C 0.88597(9) 1.04776(18) 0.44722(10) 0.0261(4) Uani 1 1 d . . . . . 
H7BA H 0.856431 1.107926 0.403284 0.031 Uiso 1 1 calc R U . . . 
H7BB H 0.933450 1.073313 0.457056 0.031 Uiso 1 1 calc R U . . . 
C8B C 0.86934(8) 1.06611(16) 0.52487(10) 0.0203(3) Uani 1 1 d . . . . . 
C9B C 0.90242(9) 1.19719(17) 0.57190(11) 0.0267(4) Uani 1 1 d . . . . . 
H9BA H 0.950893 1.194861 0.581955 0.040 Uiso 1 1 calc R U . . . 
H9BB H 0.894934 1.199755 0.623668 0.040 Uiso 1 1 calc R U . . . 
H9BC H 0.882680 1.281180 0.540294 0.040 Uiso 1 1 calc R U . . . 
C10B C 0.79259(8) 1.07684(18) 0.50387(11) 0.0264(4) Uani 1 1 d . . . . . 
H10A H 0.774938 1.154796 0.466017 0.040 Uiso 1 1 calc R U . . . 
H10B H 0.782738 1.093744 0.553416 0.040 Uiso 1 1 calc R U . . . 
H10C H 0.771280 0.988803 0.478829 0.040 Uiso 1 1 calc R U . . . 
C11B C 0.92474(8) 0.68569(17) 0.51927(10) 0.0218(3) Uani 1 1 d . . . . . 
H11A H 0.970392 0.716866 0.523445 0.026 Uiso 1 1 calc R U . . . 
H11B H 0.927924 0.642304 0.571523 0.026 Uiso 1 1 calc R U . . . 
C12B C 0.89944(8) 0.57752(16) 0.45240(9) 0.0195(3) Uani 1 1 d . . . . . 
C13B C 0.93632(8) 0.54384(17) 0.40351(10) 0.0213(3) Uani 1 1 d . . . . . 
H13B H 0.978630 0.587934 0.413145 0.026 Uiso 1 1 calc R U . . . 
C14B C 0.91278(8) 0.44719(17) 0.34086(10) 0.0220(3) Uani 1 1 d . . . . . 
H14B H 0.938695 0.424459 0.308174 0.026 Uiso 1 1 calc R U . . . 
C15B C 0.85096(8) 0.38482(17) 0.32705(9) 0.0211(3) Uani 1 1 d . . . . . 
C16B C 0.81342(8) 0.41252(17) 0.37572(10) 0.0213(3) Uani 1 1 d . . . . . 
H16B H 0.771604 0.366651 0.366632 0.026 Uiso 1 1 calc R U . . . 
C17B C 0.83852(8) 0.50919(17) 0.43823(10) 0.0211(3) Uani 1 1 d . . . . . 
H17B H 0.813303 0.529015 0.472143 0.025 Uiso 1 1 calc R U . . . 
 
 
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
 
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
Cl1A C15A 1.7490(16) . ? 
O1A C4A 1.4259(18) . ? 
O1A H1A 0.86(2) . ? 
N1A C3A 1.332(2) . ? 
N1A N2A 1.3631(19) . ? 
N1A C1A 1.459(2) . ? 
N2A C2A 1.316(2) . ? 
N3A C3A 1.326(2) . ? 
N3A C2A 1.360(2) . ? 
C1A C4A 1.530(2) . ? 
C1A H1AA 0.9900 . ? 
C1A H1AB 0.9900 . ? 
C2A H2A 0.9500 . ? 
C3A H3A 0.9500 . ? 
C4A C5A 1.540(2) . ? 
C4A C8A 1.565(2) . ? 
C5A C11A 1.532(2) . ? 
C5A C6A 1.542(2) . ? 
C5A H5A 1.0000 . ? 
C6A C7A 1.535(2) . ? 
C6A H6AA 0.9900 . ? 
C6A H6AB 0.9900 . ? 
C7A C8A 1.543(2) . ? 
C7A H7AA 0.9900 . ? 
C7A H7AB 0.9900 . ? 
C8A C9A 1.531(2) . ? 
C8A C10A 1.537(2) . ? 
C9A H9AA 0.9800 . ? 
C9A H9AB 0.9800 . ? 
C9A H9AC 0.9800 . ? 
C10A H10D 0.9800 . ? 
C10A H10E 0.9800 . ? 
C10A H10F 0.9800 . ? 
C11A C12A 1.513(2) . ? 
C11A H11C 0.9900 . ? 
C11A H11D 0.9900 . ? 
C12A C13A 1.391(2) . ? 
C12A C17A 1.396(2) . ? 
C13A C14A 1.390(2) . ? 
C13A H13A 0.9500 . ? 
C14A C15A 1.377(2) . ? 
C14A H14A 0.9500 . ? 
C15A C16A 1.388(2) . ? 
C16A C17A 1.386(2) . ? 
C16A H16A 0.9500 . ? 
C17A H17A 0.9500 . ? 
Cl1B C15B 1.7473(16) . ? 
O19B C4B 1.4250(18) . ? 
O19B H19B 0.87(2) . ? 
N1B C3B 1.333(2) . ? 
N1B N2B 1.3610(19) . ? 
N1B C1B 1.459(2) . ? 
N2B C2B 1.315(2) . ? 
N3B C3B 1.327(2) . ? 
N3B C2B 1.356(2) . ? 
C1B C4B 1.532(2) . ? 
C1B H1BA 0.9900 . ? 
C1B H1BB 0.9900 . ? 
C2B H2B 0.9500 . ? 
C3B H3B 0.9500 . ? 
C4B C5B 1.547(2) . ? 
C4B C8B 1.564(2) . ? 
C5B C11B 1.533(2) . ? 
C5B C6B 1.550(2) . ? 
C5B H5B 1.0000 . ? 
C6B C7B 1.529(2) . ? 
C6B H6BA 0.9900 . ? 
C6B H6BB 0.9900 . ? 
C7B C8B 1.539(2) . ? 
C7B H7BA 0.9900 . ? 
C7B H7BB 0.9900 . ? 
C8B C9B 1.525(2) . ? 
C8B C10B 1.540(2) . ? 
C9B H9BA 0.9800 . ? 
C9B H9BB 0.9800 . ? 
C9B H9BC 0.9800 . ? 
C10B H10A 0.9800 . ? 
C10B H10B 0.9800 . ? 
C10B H10C 0.9800 . ? 
C11B C12B 1.514(2) . ? 
C11B H11A 0.9900 . ? 
C11B H11B 0.9900 . ? 
C12B C17B 1.388(2) . ? 
C12B C13B 1.389(2) . ? 
C13B C14B 1.389(2) . ? 
C13B H13B 0.9500 . ? 
C14B C15B 1.380(2) . ? 
C14B H14B 0.9500 . ? 
C15B C16B 1.385(2) . ? 
C16B C17B 1.390(2) . ? 
C16B H16B 0.9500 . ? 
C17B H17B 0.9500 . ? 
 
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
C4A O1A H1A 109.5 . . ? 
C3A N1A N2A 109.64(13) . . ? 
C3A N1A C1A 130.13(14) . . ? 
N2A N1A C1A 120.20(13) . . ? 
C2A N2A N1A 102.20(14) . . ? 
C3A N3A C2A 102.11(14) . . ? 
N1A C1A C4A 113.96(13) . . ? 
N1A C1A H1AA 108.8 . . ? 
C4A C1A H1AA 108.8 . . ? 
N1A C1A H1AB 108.8 . . ? 
C4A C1A H1AB 108.8 . . ? 
H1AA C1A H1AB 107.7 . . ? 
N2A C2A N3A 115.29(15) . . ? 
N2A C2A H2A 122.4 . . ? 
N3A C2A H2A 122.4 . . ? 
N3A C3A N1A 110.76(15) . . ? 
N3A C3A H3A 124.6 . . ? 
N1A C3A H3A 124.6 . . ? 
O1A C4A C1A 109.12(12) . . ? 
O1A C4A C5A 106.28(12) . . ? 
C1A C4A C5A 115.75(13) . . ? 
O1A C4A C8A 111.16(12) . . ? 
C1A C4A C8A 110.99(12) . . ? 
C5A C4A C8A 103.38(12) . . ? 
C11A C5A C4A 116.03(12) . . ? 
C11A C5A C6A 112.18(13) . . ? 
C4A C5A C6A 103.95(12) . . ? 
C11A C5A H5A 108.1 . . ? 
C4A C5A H5A 108.1 . . ? 
C6A C5A H5A 108.1 . . ? 
C7A C6A C5A 106.87(13) . . ? 
C7A C6A H6AA 110.3 . . ? 
C5A C6A H6AA 110.3 . . ? 
C7A C6A H6AB 110.3 . . ? 
C5A C6A H6AB 110.3 . . ? 
H6AA C6A H6AB 108.6 . . ? 
C6A C7A C8A 106.83(13) . . ? 
C6A C7A H7AA 110.4 . . ? 
C8A C7A H7AA 110.4 . . ? 
C6A C7A H7AB 110.4 . . ? 
C8A C7A H7AB 110.4 . . ? 
H7AA C7A H7AB 108.6 . . ? 
C9A C8A C10A 107.99(13) . . ? 
C9A C8A C7A 111.36(14) . . ? 
C10A C8A C7A 110.06(13) . . ? 
C9A C8A C4A 113.57(13) . . ? 
C10A C8A C4A 112.29(13) . . ? 
C7A C8A C4A 101.50(12) . . ? 
C8A C9A H9AA 109.5 . . ? 
C8A C9A H9AB 109.5 . . ? 
H9AA C9A H9AB 109.5 . . ? 
C8A C9A H9AC 109.5 . . ? 
H9AA C9A H9AC 109.5 . . ? 
H9AB C9A H9AC 109.5 . . ? 
C8A C10A H10D 109.5 . . ? 
C8A C10A H10E 109.5 . . ? 
H10D C10A H10E 109.5 . . ? 
C8A C10A H10F 109.5 . . ? 
H10D C10A H10F 109.5 . . ? 
H10E C10A H10F 109.5 . . ? 
C12A C11A C5A 112.14(13) . . ? 
C12A C11A H11C 109.2 . . ? 
C5A C11A H11C 109.2 . . ? 
C12A C11A H11D 109.2 . . ? 
C5A C11A H11D 109.2 . . ? 
H11C C11A H11D 107.9 . . ? 
C13A C12A C17A 117.79(15) . . ? 
C13A C12A C11A 121.18(15) . . ? 
C17A C12A C11A 121.02(15) . . ? 
C14A C13A C12A 121.54(15) . . ? 
C14A C13A H13A 119.2 . . ? 
C12A C13A H13A 119.2 . . ? 
C15A C14A C13A 118.95(15) . . ? 
C15A C14A H14A 120.5 . . ? 
C13A C14A H14A 120.5 . . ? 
C14A C15A C16A 121.41(15) . . ? 
C14A C15A Cl1A 119.39(12) . . ? 
C16A C15A Cl1A 119.20(12) . . ? 
C17A C16A C15A 118.61(15) . . ? 
C17A C16A H16A 120.7 . . ? 
C15A C16A H16A 120.7 . . ? 
C16A C17A C12A 121.69(15) . . ? 
C16A C17A H17A 119.2 . . ? 
C12A C17A H17A 119.2 . . ? 
C4B O19B H19B 109.5 . . ? 
C3B N1B N2B 109.64(13) . . ? 
C3B N1B C1B 129.60(14) . . ? 
N2B N1B C1B 120.66(13) . . ? 
C2B N2B N1B 102.09(14) . . ? 
C3B N3B C2B 101.93(14) . . ? 
N1B C1B C4B 113.25(13) . . ? 
N1B C1B H1BA 108.9 . . ? 
C4B C1B H1BA 108.9 . . ? 
N1B C1B H1BB 108.9 . . ? 
C4B C1B H1BB 108.9 . . ? 
H1BA C1B H1BB 107.7 . . ? 
N2B C2B N3B 115.61(16) . . ? 
N2B C2B H2B 122.2 . . ? 
N3B C2B H2B 122.2 . . ? 
N3B C3B N1B 110.73(15) . . ? 
N3B C3B H3B 124.6 . . ? 
N1B C3B H3B 124.6 . . ? 
O19B C4B C1B 109.52(12) . . ? 
O19B C4B C5B 106.86(12) . . ? 
C1B C4B C5B 113.83(13) . . ? 
O19B C4B C8B 111.13(12) . . ? 
C1B C4B C8B 111.39(12) . . ? 
C5B C4B C8B 103.94(12) . . ? 
C11B C5B C4B 114.73(13) . . ? 
C11B C5B C6B 112.25(13) . . ? 
C4B C5B C6B 105.34(13) . . ? 
C11B C5B H5B 108.1 . . ? 
C4B C5B H5B 108.1 . . ? 
C6B C5B H5B 108.1 . . ? 
C7B C6B C5B 106.52(13) . . ? 
C7B C6B H6BA 110.4 . . ? 
C5B C6B H6BA 110.4 . . ? 
C7B C6B H6BB 110.4 . . ? 
C5B C6B H6BB 110.4 . . ? 
H6BA C6B H6BB 108.6 . . ? 
C6B C7B C8B 105.74(13) . . ? 
C6B C7B H7BA 110.6 . . ? 
C8B C7B H7BA 110.6 . . ? 
C6B C7B H7BB 110.6 . . ? 
C8B C7B H7BB 110.6 . . ? 
H7BA C7B H7BB 108.7 . . ? 
C9B C8B C7B 111.82(14) . . ? 
C9B C8B C10B 108.81(14) . . ? 
C7B C8B C10B 110.20(14) . . ? 
C9B C8B C4B 113.23(13) . . ? 
C7B C8B C4B 101.17(12) . . ? 
C10B C8B C4B 111.46(13) . . ? 
C8B C9B H9BA 109.5 . . ? 
C8B C9B H9BB 109.5 . . ? 
H9BA C9B H9BB 109.5 . . ? 
C8B C9B H9BC 109.5 . . ? 
H9BA C9B H9BC 109.5 . . ? 
H9BB C9B H9BC 109.5 . . ? 
C8B C10B H10A 109.5 . . ? 
C8B C10B H10B 109.5 . . ? 
H10A C10B H10B 109.5 . . ? 
C8B C10B H10C 109.5 . . ? 
H10A C10B H10C 109.5 . . ? 
H10B C10B H10C 109.5 . . ? 
C12B C11B C5B 111.25(13) . . ? 
C12B C11B H11A 109.4 . . ? 
C5B C11B H11A 109.4 . . ? 
C12B C11B H11B 109.4 . . ? 
C5B C11B H11B 109.4 . . ? 
H11A C11B H11B 108.0 . . ? 
C17B C12B C13B 118.08(15) . . ? 
C17B C12B C11B 120.77(14) . . ? 
C13B C12B C11B 121.14(15) . . ? 
C14B C13B C12B 121.52(15) . . ? 
C14B C13B H13B 119.2 . . ? 
C12B C13B H13B 119.2 . . ? 
C15B C14B C13B 118.66(15) . . ? 
C15B C14B H14B 120.7 . . ? 
C13B C14B H14B 120.7 . . ? 
C14B C15B C16B 121.67(15) . . ? 
C14B C15B Cl1B 119.56(12) . . ? 
C16B C15B Cl1B 118.77(13) . . ? 
C15B C16B C17B 118.28(15) . . ? 
C15B C16B H16B 120.9 . . ? 
C17B C16B H16B 120.9 . . ? 
C12B C17B C16B 121.73(15) . . ? 
C12B C17B H17B 119.1 . . ? 
C16B C17B H17B 119.1 . . ? 
 
loop_ 
 _geom_torsion_atom_site_label_1 
 _geom_torsion_atom_site_label_2 
 _geom_torsion_atom_site_label_3 
 _geom_torsion_atom_site_label_4 
 _geom_torsion 
 _geom_torsion_site_symmetry_1 
 _geom_torsion_site_symmetry_2 
 _geom_torsion_site_symmetry_3 
 _geom_torsion_site_symmetry_4 
 _geom_torsion_publ_flag 
C3A N1A N2A C2A -0.61(18) . . . . ? 
C1A N1A N2A C2A 177.59(14) . . . . ? 
C3A N1A C1A C4A 68.1(2) . . . . ? 
N2A N1A C1A C4A -109.63(16) . . . . ? 
N1A N2A C2A N3A 0.3(2) . . . . ? 
C3A N3A C2A N2A 0.2(2) . . . . ? 
C2A N3A C3A N1A -0.59(18) . . . . ? 
N2A N1A C3A N3A 0.79(19) . . . . ? 
C1A N1A C3A N3A -177.17(15) . . . . ? 
N1A C1A C4A O1A -60.01(17) . . . . ? 
N1A C1A C4A C5A 59.77(18) . . . . ? 
N1A C1A C4A C8A 177.17(12) . . . . ? 
O1A C4A C5A C11A 43.87(17) . . . . ? 
C1A C4A C5A C11A -77.44(17) . . . . ? 
C8A C4A C5A C11A 161.00(13) . . . . ? 
O1A C4A C5A C6A -79.78(14) . . . . ? 
C1A C4A C5A C6A 158.91(13) . . . . ? 
C8A C4A C5A C6A 37.35(15) . . . . ? 
C11A C5A C6A C7A -144.71(14) . . . . ? 
C4A C5A C6A C7A -18.58(17) . . . . ? 
C5A C6A C7A C8A -7.56(18) . . . . ? 
C6A C7A C8A C9A 151.19(14) . . . . ? 
C6A C7A C8A C10A -89.09(16) . . . . ? 
C6A C7A C8A C4A 30.01(17) . . . . ? 
O1A C4A C8A C9A -47.47(17) . . . . ? 
C1A C4A C8A C9A 74.17(17) . . . . ? 
C5A C4A C8A C9A -161.11(13) . . . . ? 
O1A C4A C8A C10A -170.35(13) . . . . ? 
C1A C4A C8A C10A -48.71(17) . . . . ? 
C5A C4A C8A C10A 76.01(15) . . . . ? 
O1A C4A C8A C7A 72.15(15) . . . . ? 
C1A C4A C8A C7A -166.21(13) . . . . ? 
C5A C4A C8A C7A -41.49(15) . . . . ? 
C4A C5A C11A C12A -177.53(13) . . . . ? 
C6A C5A C11A C12A -58.26(18) . . . . ? 
C5A C11A C12A C13A 113.52(17) . . . . ? 
C5A C11A C12A C17A -67.59(19) . . . . ? 
C17A C12A C13A C14A -0.3(2) . . . . ? 
C11A C12A C13A C14A 178.62(14) . . . . ? 
C12A C13A C14A C15A 0.8(2) . . . . ? 
C13A C14A C15A C16A -0.8(2) . . . . ? 
C13A C14A C15A Cl1A 179.64(12) . . . . ? 
C14A C15A C16A C17A 0.4(2) . . . . ? 
Cl1A C15A C16A C17A 179.96(12) . . . . ? 
C15A C16A C17A C12A 0.0(2) . . . . ? 
C13A C12A C17A C16A -0.1(2) . . . . ? 
C11A C12A C17A C16A -179.04(15) . . . . ? 
C3B N1B N2B C2B 0.57(19) . . . . ? 
C1B N1B N2B C2B 177.23(15) . . . . ? 
C3B N1B C1B C4B 73.5(2) . . . . ? 
N2B N1B C1B C4B -102.44(17) . . . . ? 
N1B N2B C2B N3B -0.8(2) . . . . ? 
C3B N3B C2B N2B 0.7(2) . . . . ? 
C2B N3B C3B N1B -0.28(18) . . . . ? 
N2B N1B C3B N3B -0.19(19) . . . . ? 
C1B N1B C3B N3B -176.45(15) . . . . ? 
N1B C1B C4B O19B -56.18(17) . . . . ? 
N1B C1B C4B C5B 63.35(17) . . . . ? 
N1B C1B C4B C8B -179.52(12) . . . . ? 
O19B C4B C5B C11B 34.43(17) . . . . ? 
C1B C4B C5B C11B -86.60(16) . . . . ? 
C8B C4B C5B C11B 152.03(13) . . . . ? 
O19B C4B C5B C6B -89.54(15) . . . . ? 
C1B C4B C5B C6B 149.44(14) . . . . ? 
C8B C4B C5B C6B 28.07(16) . . . . ? 
C11B C5B C6B C7B -129.92(15) . . . . ? 
C4B C5B C6B C7B -4.40(18) . . . . ? 
C5B C6B C7B C8B -21.50(19) . . . . ? 
C6B C7B C8B C9B 159.06(14) . . . . ? 
C6B C7B C8B C10B -79.78(17) . . . . ? 
C6B C7B C8B C4B 38.25(17) . . . . ? 
O19B C4B C8B C9B -45.87(17) . . . . ? 
C1B C4B C8B C9B 76.54(17) . . . . ? 
C5B C4B C8B C9B -160.47(13) . . . . ? 
O19B C4B C8B C7B 73.94(15) . . . . ? 
C1B C4B C8B C7B -163.65(13) . . . . ? 
C5B C4B C8B C7B -40.67(15) . . . . ? 
O19B C4B C8B C10B -168.95(13) . . . . ? 
C1B C4B C8B C10B -46.53(17) . . . . ? 
C5B C4B C8B C10B 76.45(15) . . . . ? 
C4B C5B C11B C12B 177.16(13) . . . . ? 
C6B C5B C11B C12B -62.64(18) . . . . ? 
C5B C11B C12B C17B -63.93(19) . . . . ? 
C5B C11B C12B C13B 116.02(16) . . . . ? 
C17B C12B C13B C14B 1.5(2) . . . . ? 
C11B C12B C13B C14B -178.49(15) . . . . ? 
C12B C13B C14B C15B 0.6(2) . . . . ? 
C13B C14B C15B C16B -2.4(2) . . . . ? 
C13B C14B C15B Cl1B 177.23(12) . . . . ? 
C14B C15B C16B C17B 2.0(2) . . . . ? 
Cl1B C15B C16B C17B -177.58(12) . . . . ? 
C13B C12B C17B C16B -1.8(2) . . . . ? 
C11B C12B C17B C16B 178.13(14) . . . . ? 
C15B C16B C17B C12B 0.1(2) . . . . ? 
 
loop_ 
 _geom_hbond_atom_site_label_D 
 _geom_hbond_atom_site_label_H 
 _geom_hbond_atom_site_label_A 
 _geom_hbond_distance_DH 
 _geom_hbond_distance_HA 
 _geom_hbond_distance_DA 
 _geom_hbond_angle_DHA 
 _geom_hbond_site_symmetry_A 
 _geom_hbond_publ_flag 
O1A H1A N3A  0.86 2.08 2.9097(18) 164.3 2_646 yes 
C2B H2B Cl1B  0.95 2.75 3.6665(18) 162.8 4_566 yes 
C2A H2A Cl1A  0.95 2.98 3.9223(18) 174.5 4_576 yes 
C16A H16A N2B  0.95 2.62 3.500(2) 155.0 . yes 
O19B H19B N3B  0.87 2.05 2.8956(18) 162.8 2_756 yes 
 
_refine_diff_density_max    0.317 
_refine_diff_density_min   -0.237 
_refine_diff_density_rms    0.048 
 
 

