# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu_dl067_kaleta_4
_database_code_depnum_ccdc_archive 'CCDC 2221718'
loop_
_audit_author_name
_audit_author_address
'Ivana Cisarova'
;Charles Univerzity
Czech Republic
;
_audit_update_record             
;
2022-11-23 deposited with the CCDC.	2023-08-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H11 N'
_chemical_formula_sum            'C12 H11 N'
_chemical_formula_weight         169.22
_chemical_compound_source        'synthesized by the authors'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
N N 0.0311 0.0180 '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                   21.5986(12)
_cell_length_b                   10.9746(6)
_cell_length_c                   7.7065(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.459(3)
_cell_angle_gamma                90
_cell_volume                     1823.39(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5563
_cell_measurement_theta_min      4.1011
_cell_measurement_theta_max      71.5737

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.303
_exptl_crystal_size_mid          0.292
_exptl_crystal_size_min          0.058
_exptl_absorpt_coefficient_mu    0.552
_shelx_estimated_absorpt_T_min   0.850
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.56
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_process_details   
;
Sevvana, M., Ruf, M., Usón, I., Sheldrick, G. M., and Herbst-Irmer, R. (2019)
"Non-merohedral twinning: from minerals to proteins"
Acta. Cryst. D75, 1040-1050.
doi:10.1107/S2059798319010179
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I\mS  micro-focus sealed tube'
_diffrn_radiation_monochromator  'Helios Cu  multilayer optic'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON III'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6824
_diffrn_reflns_av_unetI/netI     0.0902
_diffrn_reflns_av_R_equivalents  0.0904
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.049
_diffrn_reflns_theta_max         72.310
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3587
_reflns_number_gt                2373
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
  Refined as a 2-component twin.

 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       'Bruker Instrument Service vV6.2.15'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1780P)²+1.2006P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3587
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1405
_refine_ls_R_factor_gt           0.1129
_refine_ls_wR_factor_ref         0.3468
_refine_ls_wR_factor_gt          0.3267
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.000
_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
N1A N 0.95090(14) 0.3638(3) 0.9611(4) 0.0527(8) Uani 1 1 d . . . . .
C2A C 0.92642(17) 0.4600(3) 0.8733(5) 0.0498(9) Uani 1 1 d . . . . .
H2A H 0.952778 0.527440 0.854423 0.060 Uiso 1 1 calc R U . . .
C3A C 0.86605(16) 0.4671(3) 0.8095(5) 0.0474(9) Uani 1 1 d . . . . .
H3A H 0.851938 0.538178 0.748817 0.057 Uiso 1 1 calc R U . . .
C4A C 0.82483(16) 0.3709(3) 0.8327(4) 0.0427(8) Uani 1 1 d . . . . .
C5A C 0.85021(16) 0.2708(3) 0.9245(5) 0.0478(8) Uani 1 1 d . . . . .
H5A H 0.824843 0.202430 0.946108 0.057 Uiso 1 1 calc R U . . .
C6A C 0.91148(16) 0.2708(3) 0.9833(5) 0.0512(9) Uani 1 1 d . . . . .
H6A H 0.927079 0.200638 1.043551 0.061 Uiso 1 1 calc R U . . .
C7A C 0.75869(15) 0.3755(3) 0.7680(4) 0.0423(8) Uani 1 1 d . . . . .
C8A C 0.73607(16) 0.4681(3) 0.6546(4) 0.0456(8) Uani 1 1 d . . . . .
H8A H 0.763674 0.528851 0.617325 0.055 Uiso 1 1 calc R U . . .
C9A C 0.67458(16) 0.4719(3) 0.5971(4) 0.0467(8) Uani 1 1 d . . . . .
H9A H 0.660650 0.537335 0.524097 0.056 Uiso 1 1 calc R U . . .
C10A C 0.63206(17) 0.3843(3) 0.6412(4) 0.0468(8) Uani 1 1 d . . . . .
C11A C 0.65451(16) 0.2917(3) 0.7560(5) 0.0486(9) Uani 1 1 d . . . . .
H11A H 0.626649 0.231349 0.792992 0.058 Uiso 1 1 calc R U . . .
C12A C 0.71556(16) 0.2870(3) 0.8150(4) 0.0460(8) Uani 1 1 d . . . . .
H12A H 0.729183 0.222306 0.889675 0.055 Uiso 1 1 calc R U . . .
C13A C 0.56551(17) 0.3895(4) 0.5793(5) 0.0556(10) Uani 1 1 d . . . . .
H13A H 0.550395 0.306892 0.553370 0.083 Uiso 1 1 calc R U . . .
H13B H 0.560975 0.439493 0.473989 0.083 Uiso 1 1 calc R U . . .
H13C H 0.541332 0.425509 0.669932 0.083 Uiso 1 1 calc R U . . .
N1B N 0.54457(14) 0.6341(3) 0.0870(4) 0.0558(8) Uani 1 1 d . . . . .
C2B C 0.57261(17) 0.7271(3) 0.1747(5) 0.0556(10) Uani 1 1 d . . . . .
H2B H 0.548066 0.795582 0.201630 0.067 Uiso 1 1 calc R U . . .
C3B C 0.63415(17) 0.7290(3) 0.2273(5) 0.0498(9) Uani 1 1 d . . . . .
H3B H 0.650837 0.798281 0.287429 0.060 Uiso 1 1 calc R U . . .
C4B C 0.67282(16) 0.6314(3) 0.1946(4) 0.0441(8) Uani 1 1 d . . . . .
C5B C 0.64375(17) 0.5346(3) 0.1005(5) 0.0507(9) Uani 1 1 d . . . . .
H5B H 0.667322 0.465788 0.069381 0.061 Uiso 1 1 calc R U . . .
C6B C 0.58163(17) 0.5399(3) 0.0540(5) 0.0541(9) Uani 1 1 d . . . . .
H6B H 0.563463 0.471976 -0.006046 0.065 Uiso 1 1 calc R U . . .
C7B C 0.73934(16) 0.6292(3) 0.2509(4) 0.0423(8) Uani 1 1 d . . . . .
C8B C 0.76658(16) 0.7204(3) 0.3579(4) 0.0464(8) Uani 1 1 d . . . . .
H8B H 0.741502 0.785497 0.394764 0.056 Uiso 1 1 calc R U . . .
C9B C 0.82827(16) 0.7184(3) 0.4108(4) 0.0456(8) Uani 1 1 d . . . . .
H9B H 0.844822 0.782054 0.483092 0.055 Uiso 1 1 calc R U . . .
C10B C 0.86752(17) 0.6249(3) 0.3612(4) 0.0460(8) Uani 1 1 d . . . . .
C11B C 0.84082(16) 0.5329(3) 0.2555(4) 0.0478(9) Uani 1 1 d . . . . .
H11B H 0.866138 0.468130 0.218831 0.057 Uiso 1 1 calc R U . . .
C12B C 0.77892(16) 0.5340(3) 0.2036(4) 0.0468(8) Uani 1 1 d . . . . .
H12B H 0.762258 0.469032 0.134064 0.056 Uiso 1 1 calc R U . . .
C13B C 0.93541(17) 0.6249(4) 0.4141(5) 0.0576(10) Uani 1 1 d . . . . .
H13D H 0.946575 0.547590 0.471489 0.086 Uiso 1 1 calc R U . . .
H13E H 0.944784 0.692442 0.494557 0.086 Uiso 1 1 calc R U . . .
H13F H 0.959287 0.634551 0.310784 0.086 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
N1A C2A 1.345(5) . ?
N1A C6A 1.347(4) . ?
C2A C3A 1.368(5) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.399(5) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.400(5) . ?
C4A C7A 1.485(5) . ?
C5A C6A 1.373(5) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C7A C12A 1.407(4) . ?
C7A C8A 1.409(4) . ?
C8A C9A 1.375(5) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.386(5) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.414(5) . ?
C10A C13A 1.488(5) . ?
C11A C12A 1.369(5) . ?
C11A H11A 0.9500 . ?
C12A H12A 0.9500 . ?
C13A H13A 0.9800 . ?
C13A H13B 0.9800 . ?
C13A H13C 0.9800 . ?
N1B C6B 1.341(5) . ?
N1B C2B 1.347(5) . ?
C2B C3B 1.366(5) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.390(5) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.412(5) . ?
C4B C7B 1.476(5) . ?
C5B C6B 1.369(5) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
C7B C8B 1.403(4) . ?
C7B C12B 1.412(4) . ?
C8B C9B 1.370(5) . ?
C8B H8B 0.9500 . ?
C9B C10B 1.398(5) . ?
C9B H9B 0.9500 . ?
C10B C11B 1.400(5) . ?
C10B C13B 1.498(5) . ?
C11B C12B 1.372(5) . ?
C11B H11B 0.9500 . ?
C12B H12B 0.9500 . ?
C13B H13D 0.9800 . ?
C13B H13E 0.9800 . ?
C13B H13F 0.9800 . ?

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
C2A N1A C6A 115.3(3) . . ?
N1A C2A C3A 124.2(3) . . ?
N1A C2A H2A 117.9 . . ?
C3A C2A H2A 117.9 . . ?
C2A C3A C4A 120.7(3) . . ?
C2A C3A H3A 119.6 . . ?
C4A C3A H3A 119.6 . . ?
C3A C4A C5A 115.1(3) . . ?
C3A C4A C7A 122.6(3) . . ?
C5A C4A C7A 122.3(3) . . ?
C6A C5A C4A 120.5(3) . . ?
C6A C5A H5A 119.8 . . ?
C4A C5A H5A 119.8 . . ?
N1A C6A C5A 124.2(3) . . ?
N1A C6A H6A 117.9 . . ?
C5A C6A H6A 117.9 . . ?
C12A C7A C8A 116.5(3) . . ?
C12A C7A C4A 121.9(3) . . ?
C8A C7A C4A 121.5(3) . . ?
C9A C8A C7A 120.9(3) . . ?
C9A C8A H8A 119.6 . . ?
C7A C8A H8A 119.6 . . ?
C8A C9A C10A 122.8(3) . . ?
C8A C9A H9A 118.6 . . ?
C10A C9A H9A 118.6 . . ?
C9A C10A C11A 116.4(3) . . ?
C9A C10A C13A 122.4(3) . . ?
C11A C10A C13A 121.1(3) . . ?
C12A C11A C10A 121.4(3) . . ?
C12A C11A H11A 119.3 . . ?
C10A C11A H11A 119.3 . . ?
C11A C12A C7A 121.9(3) . . ?
C11A C12A H12A 119.1 . . ?
C7A C12A H12A 119.1 . . ?
C10A C13A H13A 109.5 . . ?
C10A C13A H13B 109.5 . . ?
H13A C13A H13B 109.5 . . ?
C10A C13A H13C 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C6B N1B C2B 115.1(3) . . ?
N1B C2B C3B 124.1(3) . . ?
N1B C2B H2B 118.0 . . ?
C3B C2B H2B 118.0 . . ?
C2B C3B C4B 121.2(3) . . ?
C2B C3B H3B 119.4 . . ?
C4B C3B H3B 119.4 . . ?
C3B C4B C5B 114.8(3) . . ?
C3B C4B C7B 123.0(3) . . ?
C5B C4B C7B 122.3(3) . . ?
C6B C5B C4B 120.1(3) . . ?
C6B C5B H5B 120.0 . . ?
C4B C5B H5B 120.0 . . ?
N1B C6B C5B 124.7(3) . . ?
N1B C6B H6B 117.6 . . ?
C5B C6B H6B 117.6 . . ?
C8B C7B C12B 116.1(3) . . ?
C8B C7B C4B 121.8(3) . . ?
C12B C7B C4B 122.0(3) . . ?
C9B C8B C7B 121.9(3) . . ?
C9B C8B H8B 119.0 . . ?
C7B C8B H8B 119.0 . . ?
C8B C9B C10B 121.7(3) . . ?
C8B C9B H9B 119.2 . . ?
C10B C9B H9B 119.2 . . ?
C9B C10B C11B 116.9(3) . . ?
C9B C10B C13B 121.7(3) . . ?
C11B C10B C13B 121.3(3) . . ?
C12B C11B C10B 121.5(3) . . ?
C12B C11B H11B 119.2 . . ?
C10B C11B H11B 119.2 . . ?
C11B C12B C7B 121.8(3) . . ?
C11B C12B H12B 119.1 . . ?
C7B C12B H12B 119.1 . . ?
C10B C13B H13D 109.5 . . ?
C10B C13B H13E 109.5 . . ?
H13D C13B H13E 109.5 . . ?
C10B C13B H13F 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?

_refine_diff_density_max         0.464
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.095

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_dl071_kaleta
_database_code_depnum_ccdc_archive 'CCDC 2221719'
loop_
_audit_author_name
_audit_author_address
'Ivana Cisarova'
;Charles Univerzity
Czech Republic
;
_audit_update_record             
;
2022-11-23 deposited with the CCDC.	2023-08-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H14 N, I'
_chemical_formula_sum            'C13 H14 I N'
_chemical_formula_weight         311.15
_chemical_compound_source        'synthesized by the authors'

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'
I I -0.4742 1.8119 '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'

_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                   13.0447(10)
_cell_length_b                   8.5595(6)
_cell_length_c                   11.9652(8)
_cell_angle_alpha                90
_cell_angle_beta                 112.440(2)
_cell_angle_gamma                90
_cell_volume                     1234.83(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9946
_cell_measurement_theta_min      2.9185
_cell_measurement_theta_max      27.5248

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless-yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.674
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.271
_exptl_crystal_size_mid          0.234
_exptl_crystal_size_min          0.054
_exptl_absorpt_coefficient_mu    2.562
_shelx_estimated_absorpt_T_min   0.544
_shelx_estimated_absorpt_T_max   0.874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.57
_exptl_absorpt_correction_T_max  0.87
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS  micro-focus sealed tube'
_diffrn_radiation_monochromator  'Quazar Mo multilayer optic'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTONIII CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10218
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.918
_diffrn_reflns_theta_max         27.555
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2826
_reflns_number_gt                2596
_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       'Bruker Instrument Service vV6.2.15'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+10.5358P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2826
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.1169
_refine_ls_wR_factor_gt          0.1154
_refine_ls_goodness_of_fit_ref   1.404
_refine_ls_restrained_S_all      1.404
_refine_ls_shift/su_max          0.000
_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
I1 I 0.35020(3) 0.25397(5) -0.15449(4) 0.02494(14) Uani 1 1 d . . . . .
N1 N 0.6167(4) 0.2539(7) 0.2920(5) 0.0247(11) Uani 1 1 d . . . . .
C2 C 0.6338(5) 0.3923(7) 0.3493(6) 0.0229(13) Uani 1 1 d . . . . .
H2 H 0.600324 0.484240 0.306336 0.027 Uiso 1 1 calc R U . . .
C3 C 0.7002(6) 0.4006(7) 0.4708(6) 0.0222(13) Uani 1 1 d . . . . .
H3 H 0.712820 0.498840 0.510776 0.027 Uiso 1 1 calc R U . . .
C4 C 0.7492(5) 0.2663(7) 0.5359(6) 0.0222(12) Uani 1 1 d . . . . .
C5 C 0.7237(6) 0.1231(7) 0.4724(7) 0.0252(14) Uani 1 1 d . . . . .
H5 H 0.751387 0.028086 0.514002 0.030 Uiso 1 1 calc R U . . .
C6 C 0.6601(5) 0.1206(8) 0.3532(7) 0.0256(14) Uani 1 1 d . . . . .
H6 H 0.645557 0.023686 0.311317 0.031 Uiso 1 1 calc R U . . .
C7 C 0.8270(5) 0.2727(7) 0.6630(6) 0.0225(12) Uani 1 1 d . . . . .
C8 C 0.8958(6) 0.4011(8) 0.7057(6) 0.0262(14) Uani 1 1 d . . . . .
H8 H 0.888227 0.489011 0.654670 0.031 Uiso 1 1 calc R U . . .
C9 C 0.9750(6) 0.4021(8) 0.8216(6) 0.0285(14) Uani 1 1 d . . . . .
H9 H 1.022692 0.490000 0.848003 0.034 Uiso 1 1 calc R U . . .
C10 C 0.9874(5) 0.2790(7) 0.9008(6) 0.0241(13) Uani 1 1 d . . . . .
C11 C 0.9158(5) 0.1511(7) 0.8588(6) 0.0234(13) Uani 1 1 d . . . . .
H11 H 0.920871 0.066210 0.911789 0.028 Uiso 1 1 calc R U . . .
C12 C 0.8386(5) 0.1463(7) 0.7424(6) 0.0225(13) Uani 1 1 d . . . . .
H12 H 0.792495 0.056970 0.715179 0.027 Uiso 1 1 calc R U . . .
C13 C 0.5446(6) 0.2512(9) 0.1617(6) 0.0303(14) Uani 1 1 d . . . . .
H13A H 0.554164 0.151688 0.126324 0.045 Uiso 1 1 calc R U . . .
H13B H 0.564977 0.337456 0.120350 0.045 Uiso 1 1 calc R U . . .
H13C H 0.466922 0.262689 0.152106 0.045 Uiso 1 1 calc R U . . .
C14 C 1.0792(6) 0.2785(8) 1.0256(6) 0.0334(15) Uani 1 1 d . . . . .
H14A H 1.050754 0.235809 1.084151 0.050 Uiso 1 1 calc R U . . .
H14B H 1.105315 0.385570 1.048647 0.050 Uiso 1 1 calc R U . . .
H14C H 1.140835 0.213758 1.024683 0.050 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
N1 C2 1.344(8) . ?
N1 C6 1.358(9) . ?
N1 C13 1.483(8) . ?
C2 C3 1.382(10) . ?
C2 H2 0.9500 . ?
C3 C4 1.398(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.413(9) . ?
C4 C7 1.472(9) . ?
C5 C6 1.349(10) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.388(9) . ?
C7 C12 1.410(8) . ?
C8 C9 1.377(10) . ?
C8 H8 0.9500 . ?
C9 C10 1.384(9) . ?
C9 H9 0.9500 . ?
C10 C11 1.402(8) . ?
C10 C14 1.516(9) . ?
C11 C12 1.373(9) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

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
C2 N1 C6 120.8(6) . . ?
C2 N1 C13 117.8(6) . . ?
C6 N1 C13 121.4(6) . . ?
N1 C2 C3 119.8(6) . . ?
N1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C2 C3 C4 120.9(6) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 116.8(6) . . ?
C3 C4 C7 122.2(6) . . ?
C5 C4 C7 121.0(6) . . ?
C6 C5 C4 120.4(6) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 N1 121.2(6) . . ?
C5 C6 H6 119.4 . . ?
N1 C6 H6 119.4 . . ?
C8 C7 C12 118.2(6) . . ?
C8 C7 C4 120.3(6) . . ?
C12 C7 C4 121.5(6) . . ?
C9 C8 C7 120.5(6) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 122.1(6) . . ?
C8 C9 H9 119.0 . . ?
C10 C9 H9 119.0 . . ?
C9 C10 C11 117.5(6) . . ?
C9 C10 C14 121.2(6) . . ?
C11 C10 C14 121.2(6) . . ?
C12 C11 C10 121.2(6) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C7 120.6(6) . . ?
C11 C12 H12 119.7 . . ?
C7 C12 H12 119.7 . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_refine_diff_density_max         1.111
_refine_diff_density_min         -1.099
_refine_diff_density_rms         0.142

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu_dl074_kaleta
_database_code_depnum_ccdc_archive 'CCDC 2221720'
loop_
_audit_author_name
_audit_author_address
'Ivana Cisarova'
;Charles Univerzity
Czech Republic
;
_audit_update_record             
;
2022-11-23 deposited with the CCDC.	2023-08-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C22 H26 N), 2(Cl), H2 O'
_chemical_formula_sum            'C44 H54 Cl2 N2 O'
_chemical_formula_weight         697.79
_chemical_compound_source        'synthesized by the authors'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   18.5283(4)
_cell_length_b                   9.7746(2)
_cell_length_c                   20.5000(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.9010(10)
_cell_angle_gamma                90
_cell_volume                     3667.98(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9805
_cell_measurement_theta_min      2.9931
_cell_measurement_theta_max      72.0951

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_F_000             1496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.196
_exptl_crystal_size_min          0.076
_exptl_absorpt_coefficient_mu    1.867
_shelx_estimated_absorpt_T_min   0.694
_shelx_estimated_absorpt_T_max   0.871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.73
_exptl_absorpt_correction_T_max  0.87
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I\mS  micro-focus sealed tube'
_diffrn_radiation_monochromator  'Helios Cu  multilayer optic'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON III'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40378
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.993
_diffrn_reflns_theta_max         72.094
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7203
_reflns_number_gt                6887
_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       'Bruker Instrument Service vV6.2.15'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0373P)²+1.6142P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7203
_refine_ls_number_parameters     444
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0296
_refine_ls_wR_factor_ref         0.0797
_refine_ls_wR_factor_gt          0.0786
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.002
_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
Cl1 Cl 0.59093(2) 0.19505(3) 0.45987(2) 0.02140(8) Uani 1 1 d . . . . .
Cl2 Cl 0.52108(2) 0.39147(3) 0.19405(2) 0.02134(8) Uani 1 1 d . . . . .
C1A C 0.81594(6) 0.14232(12) 0.42165(5) 0.0155(2) Uani 1 1 d . . . . .
C2A C 0.78063(6) 0.02001(12) 0.45134(5) 0.0183(2) Uani 1 1 d . . . . .
H2AA H 0.794425 -0.066040 0.430969 0.022 Uiso 1 1 calc R U . . .
H2AB H 0.726766 0.028660 0.442554 0.022 Uiso 1 1 calc R U . . .
C3A C 0.80727(6) 0.01704(12) 0.52639(6) 0.0202(2) Uani 1 1 d . . . . .
H3A H 0.784844 -0.062747 0.546304 0.024 Uiso 1 1 calc R U . . .
C4A C 0.89078(7) 0.00396(12) 0.53983(6) 0.0216(2) Uani 1 1 d . . . . .
H4AA H 0.907750 0.000585 0.588026 0.026 Uiso 1 1 calc R U . . .
H4AB H 0.905851 -0.081915 0.520148 0.026 Uiso 1 1 calc R U . . .
C5A C 0.92547(6) 0.12643(12) 0.50993(6) 0.0191(2) Uani 1 1 d . . . . .
H5A H 0.979846 0.116932 0.518714 0.023 Uiso 1 1 calc R U . . .
C6A C 0.89972(6) 0.12898(12) 0.43477(6) 0.0190(2) Uani 1 1 d . . . . .
H6AA H 0.922246 0.207293 0.414817 0.023 Uiso 1 1 calc R U . . .
H6AB H 0.914805 0.043692 0.414582 0.023 Uiso 1 1 calc R U . . .
C7A C 0.79362(6) 0.27580(12) 0.45285(5) 0.0171(2) Uani 1 1 d . . . . .
H7AA H 0.815580 0.355005 0.433085 0.021 Uiso 1 1 calc R U . . .
H7AB H 0.739832 0.286053 0.444189 0.021 Uiso 1 1 calc R U . . .
C8A C 0.82016(6) 0.27194(12) 0.52766(5) 0.0183(2) Uani 1 1 d . . . . .
H8A H 0.805317 0.358527 0.547928 0.022 Uiso 1 1 calc R U . . .
C9A C 0.78463(6) 0.15019(13) 0.55760(6) 0.0207(2) Uani 1 1 d . . . . .
H9AA H 0.730799 0.159778 0.549105 0.025 Uiso 1 1 calc R U . . .
H9AB H 0.800506 0.147850 0.605971 0.025 Uiso 1 1 calc R U . . .
C10A C 0.90350(6) 0.25919(12) 0.54126(6) 0.0197(2) Uani 1 1 d . . . . .
H10A H 0.926157 0.338474 0.522209 0.024 Uiso 1 1 calc R U . . .
H10B H 0.920640 0.257736 0.589457 0.024 Uiso 1 1 calc R U . . .
N11A N 0.78854(5) 0.14427(10) 0.34757(5) 0.01582(19) Uani 1 1 d . . . . .
C12A C 0.82542(6) 0.07839(12) 0.30503(6) 0.0197(2) Uani 1 1 d . . . . .
H12A H 0.869764 0.032830 0.321611 0.024 Uiso 1 1 calc R U . . .
C13A C 0.80029(6) 0.07573(12) 0.23839(6) 0.0197(2) Uani 1 1 d . . . . .
H13A H 0.827518 0.028650 0.209756 0.024 Uiso 1 1 calc R U . . .
C14A C 0.73513(6) 0.14143(11) 0.21208(5) 0.0163(2) Uani 1 1 d . . . . .
C15A C 0.69752(6) 0.20730(13) 0.25729(6) 0.0214(2) Uani 1 1 d . . . . .
H15A H 0.652861 0.253040 0.242000 0.026 Uiso 1 1 calc R U . . .
C16A C 0.72456(6) 0.20639(13) 0.32349(6) 0.0230(3) Uani 1 1 d . . . . .
H16A H 0.697667 0.250576 0.353300 0.028 Uiso 1 1 calc R U . . .
C17A C 0.70728(6) 0.14067(11) 0.14054(5) 0.0163(2) Uani 1 1 d . . . . .
C18A C 0.75484(6) 0.12343(12) 0.09438(6) 0.0190(2) Uani 1 1 d . . . . .
H18A H 0.805546 0.110443 0.109168 0.023 Uiso 1 1 calc R U . . .
C19A C 0.72865(7) 0.12513(12) 0.02729(6) 0.0204(2) Uani 1 1 d . . . . .
H19A H 0.762010 0.116041 -0.003279 0.025 Uiso 1 1 calc R U . . .
C20A C 0.65452(7) 0.13986(12) 0.00381(6) 0.0199(2) Uani 1 1 d . . . . .
C21A C 0.60713(7) 0.15516(13) 0.04990(6) 0.0229(2) Uani 1 1 d . . . . .
H21A H 0.556216 0.164193 0.034919 0.027 Uiso 1 1 calc R U . . .
C22A C 0.63269(6) 0.15748(13) 0.11715(6) 0.0211(2) Uani 1 1 d . . . . .
H22A H 0.599420 0.170549 0.147518 0.025 Uiso 1 1 calc R U . . .
C23A C 0.62648(8) 0.13805(13) -0.06926(6) 0.0268(3) Uani 1 1 d . . . . .
H23A H 0.592779 0.214744 -0.080483 0.040 Uiso 1 1 calc R U . . .
H23B H 0.600805 0.051747 -0.080987 0.040 Uiso 1 1 calc R U . . .
H23C H 0.667642 0.146489 -0.093811 0.040 Uiso 1 1 calc R U . . .
C1B C 0.52135(6) 0.81573(11) 0.36275(5) 0.0163(2) Uani 1 1 d . . . . .
C2B C 0.58491(6) 0.88867(13) 0.33738(6) 0.0216(2) Uani 1 1 d . . . . .
H2BA H 0.623792 0.822005 0.332033 0.026 Uiso 1 1 calc R U . . .
H2BB H 0.605871 0.959248 0.369453 0.026 Uiso 1 1 calc R U . . .
C3B C 0.55596(7) 0.95574(14) 0.27056(6) 0.0266(3) Uani 1 1 d . . . . .
H3B H 0.596977 1.003669 0.253579 0.032 Uiso 1 1 calc R U . . .
C4B C 0.52406(7) 0.84673(15) 0.22082(6) 0.0286(3) Uani 1 1 d . . . . .
H4BA H 0.562326 0.779407 0.214594 0.034 Uiso 1 1 calc R U . . .
H4BB H 0.506402 0.890028 0.177643 0.034 Uiso 1 1 calc R U . . .
C5B C 0.46078(7) 0.77429(13) 0.24630(6) 0.0233(3) Uani 1 1 d . . . . .
H5B H 0.440012 0.702847 0.213809 0.028 Uiso 1 1 calc R U . . .
C6B C 0.48955(7) 0.70587(12) 0.31296(6) 0.0205(2) Uani 1 1 d . . . . .
H6BA H 0.449237 0.657207 0.329638 0.025 Uiso 1 1 calc R U . . .
H6BB H 0.527808 0.638225 0.307138 0.025 Uiso 1 1 calc R U . . .
C7B C 0.46135(6) 0.91875(12) 0.37226(6) 0.0185(2) Uani 1 1 d . . . . .
H7BA H 0.481187 0.989195 0.404875 0.022 Uiso 1 1 calc R U . . .
H7BB H 0.420696 0.871294 0.388998 0.022 Uiso 1 1 calc R U . . .
C8B C 0.43343(7) 0.98642(12) 0.30535(6) 0.0213(2) Uani 1 1 d . . . . .
H8B H 0.394730 1.054645 0.311202 0.026 Uiso 1 1 calc R U . . .
C9B C 0.49687(7) 1.06008(13) 0.28033(6) 0.0263(3) Uani 1 1 d . . . . .
H9BA H 0.478997 1.106421 0.237963 0.032 Uiso 1 1 calc R U . . .
H9BB H 0.517563 1.130307 0.312706 0.032 Uiso 1 1 calc R U . . .
C10B C 0.40111(7) 0.87815(13) 0.25530(6) 0.0223(2) Uani 1 1 d . . . . .
H10C H 0.382457 0.922155 0.212507 0.027 Uiso 1 1 calc R U . . .
H10D H 0.359884 0.831149 0.271323 0.027 Uiso 1 1 calc R U . . .
N11B N 0.55059(5) 0.75160(10) 0.42942(4) 0.01551(19) Uani 1 1 d . . . . .
C12B C 0.55457(6) 0.61460(11) 0.43718(6) 0.0177(2) Uani 1 1 d . . . . .
H12B H 0.537415 0.557193 0.400673 0.021 Uiso 1 1 calc R U . . .
C13B C 0.58287(6) 0.55598(12) 0.49671(6) 0.0180(2) Uani 1 1 d . . . . .
H13B H 0.586342 0.459248 0.500472 0.022 Uiso 1 1 calc R U . . .
C14B C 0.60647(6) 0.63804(12) 0.55153(5) 0.0166(2) Uani 1 1 d . . . . .
C15B C 0.60219(6) 0.77952(12) 0.54205(6) 0.0178(2) Uani 1 1 d . . . . .
H15B H 0.618342 0.838920 0.578034 0.021 Uiso 1 1 calc R U . . .
C16B C 0.57494(6) 0.83405(12) 0.48138(6) 0.0174(2) Uani 1 1 d . . . . .
H16B H 0.573164 0.930538 0.475817 0.021 Uiso 1 1 calc R U . . .
C17B C 0.63630(6) 0.57679(12) 0.61605(5) 0.0170(2) Uani 1 1 d . . . . .
C18B C 0.68292(6) 0.46379(13) 0.61936(6) 0.0217(2) Uani 1 1 d . . . . .
H18B H 0.694120 0.423945 0.579859 0.026 Uiso 1 1 calc R U . . .
C19B C 0.71298(7) 0.40945(13) 0.68011(6) 0.0229(3) Uani 1 1 d . . . . .
H19B H 0.746197 0.335051 0.681699 0.027 Uiso 1 1 calc R U . . .
C20B C 0.69526(6) 0.46218(12) 0.73879(6) 0.0195(2) Uani 1 1 d . . . . .
C21B C 0.64606(6) 0.57123(12) 0.73504(6) 0.0197(2) Uani 1 1 d . . . . .
H21B H 0.631807 0.606240 0.774367 0.024 Uiso 1 1 calc R U . . .
C22B C 0.61775(6) 0.62907(12) 0.67479(6) 0.0183(2) Uani 1 1 d . . . . .
H22B H 0.585458 0.704885 0.673348 0.022 Uiso 1 1 calc R U . . .
C23B C 0.72683(7) 0.40147(14) 0.80469(6) 0.0258(3) Uani 1 1 d . . . . .
H23D H 0.687614 0.386390 0.830941 0.039 Uiso 1 1 calc R U . . .
H23E H 0.762977 0.464536 0.828165 0.039 Uiso 1 1 calc R U . . .
H23F H 0.750415 0.314052 0.797773 0.039 Uiso 1 1 calc R U . . .
O1W O 0.59113(5) 0.39817(8) 0.34188(4) 0.02159(18) Uani 1 1 d . . . . .
H1W H 0.563377 0.383877 0.303155 0.026 Uiso 1 1 d R U . . .
H2W H 0.581877 0.335977 0.369655 0.026 Uiso 1 1 d 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
C1A N11A 1.5250(13) . ?
C1A C2A 1.5332(15) . ?
C1A C7A 1.5376(15) . ?
C1A C6A 1.5395(15) . ?
C2A C3A 1.5417(15) . ?
C2A H2AA 0.9900 . ?
C2A H2AB 0.9900 . ?
C3A C4A 1.5345(16) . ?
C3A C9A 1.5370(16) . ?
C3A H3A 1.0000 . ?
C4A C5A 1.5308(17) . ?
C4A H4AA 0.9900 . ?
C4A H4AB 0.9900 . ?
C5A C10A 1.5307(16) . ?
C5A C6A 1.5411(15) . ?
C5A H5A 1.0000 . ?
C6A H6AA 0.9900 . ?
C6A H6AB 0.9900 . ?
C7A C8A 1.5368(15) . ?
C7A H7AA 0.9900 . ?
C7A H7AB 0.9900 . ?
C8A C10A 1.5311(15) . ?
C8A C9A 1.5335(16) . ?
C8A H8A 1.0000 . ?
C9A H9AA 0.9900 . ?
C9A H9AB 0.9900 . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
N11A C12A 1.3514(15) . ?
N11A C16A 1.3552(15) . ?
C12A C13A 1.3737(16) . ?
C12A H12A 0.9500 . ?
C13A C14A 1.3998(16) . ?
C13A H13A 0.9500 . ?
C14A C15A 1.3996(16) . ?
C14A C17A 1.4775(15) . ?
C15A C16A 1.3720(17) . ?
C15A H15A 0.9500 . ?
C16A H16A 0.9500 . ?
C17A C18A 1.3994(16) . ?
C17A C22A 1.4007(16) . ?
C18A C19A 1.3859(16) . ?
C18A H18A 0.9500 . ?
C19A C20A 1.3908(17) . ?
C19A H19A 0.9500 . ?
C20A C21A 1.3938(17) . ?
C20A C23A 1.5078(16) . ?
C21A C22A 1.3868(17) . ?
C21A H21A 0.9500 . ?
C22A H22A 0.9500 . ?
C23A H23A 0.9800 . ?
C23A H23B 0.9800 . ?
C23A H23C 0.9800 . ?
C1B N11B 1.5249(14) . ?
C1B C2B 1.5346(16) . ?
C1B C7B 1.5348(15) . ?
C1B C6B 1.5350(15) . ?
C2B C3B 1.5383(16) . ?
C2B H2BA 0.9900 . ?
C2B H2BB 0.9900 . ?
C3B C4B 1.5290(19) . ?
C3B C9B 1.5320(19) . ?
C3B H3B 1.0000 . ?
C4B C5B 1.5291(19) . ?
C4B H4BA 0.9900 . ?
C4B H4BB 0.9900 . ?
C5B C10B 1.5330(17) . ?
C5B C6B 1.5406(16) . ?
C5B H5B 1.0000 . ?
C6B H6BA 0.9900 . ?
C6B H6BB 0.9900 . ?
C7B C8B 1.5385(15) . ?
C7B H7BA 0.9900 . ?
C7B H7BB 0.9900 . ?
C8B C10B 1.5301(16) . ?
C8B C9B 1.5329(18) . ?
C8B H8B 1.0000 . ?
C9B H9BA 0.9900 . ?
C9B H9BB 0.9900 . ?
C10B H10C 0.9900 . ?
C10B H10D 0.9900 . ?
N11B C12B 1.3493(15) . ?
N11B C16B 1.3561(14) . ?
C12B C13B 1.3763(16) . ?
C12B H12B 0.9500 . ?
C13B C14B 1.3948(16) . ?
C13B H13B 0.9500 . ?
C14B C15B 1.3970(16) . ?
C14B C17B 1.4789(15) . ?
C15B C16B 1.3753(16) . ?
C15B H15B 0.9500 . ?
C16B H16B 0.9500 . ?
C17B C18B 1.3974(16) . ?
C17B C22B 1.3990(16) . ?
C18B C19B 1.3887(17) . ?
C18B H18B 0.9500 . ?
C19B C20B 1.3938(17) . ?
C19B H19B 0.9500 . ?
C20B C21B 1.3970(17) . ?
C20B C23B 1.5082(16) . ?
C21B C22B 1.3857(16) . ?
C21B H21B 0.9500 . ?
C22B H22B 0.9500 . ?
C23B H23D 0.9800 . ?
C23B H23E 0.9800 . ?
C23B H23F 0.9800 . ?
O1W H1W 0.8875 . ?
O1W H2W 0.8680 . ?

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
N11A C1A C2A 107.96(9) . . ?
N11A C1A C7A 109.52(9) . . ?
C2A C1A C7A 109.74(9) . . ?
N11A C1A C6A 110.26(8) . . ?
C2A C1A C6A 110.20(9) . . ?
C7A C1A C6A 109.15(9) . . ?
C1A C2A C3A 108.69(9) . . ?
C1A C2A H2AA 110.0 . . ?
C3A C2A H2AA 110.0 . . ?
C1A C2A H2AB 110.0 . . ?
C3A C2A H2AB 110.0 . . ?
H2AA C2A H2AB 108.3 . . ?
C4A C3A C9A 109.17(9) . . ?
C4A C3A C2A 109.81(9) . . ?
C9A C3A C2A 109.49(9) . . ?
C4A C3A H3A 109.5 . . ?
C9A C3A H3A 109.5 . . ?
C2A C3A H3A 109.5 . . ?
C5A C4A C3A 109.70(9) . . ?
C5A C4A H4AA 109.7 . . ?
C3A C4A H4AA 109.7 . . ?
C5A C4A H4AB 109.7 . . ?
C3A C4A H4AB 109.7 . . ?
H4AA C4A H4AB 108.2 . . ?
C10A C5A C4A 109.85(10) . . ?
C10A C5A C6A 110.15(9) . . ?
C4A C5A C6A 109.20(9) . . ?
C10A C5A H5A 109.2 . . ?
C4A C5A H5A 109.2 . . ?
C6A C5A H5A 109.2 . . ?
C1A C6A C5A 108.89(9) . . ?
C1A C6A H6AA 109.9 . . ?
C5A C6A H6AA 109.9 . . ?
C1A C6A H6AB 109.9 . . ?
C5A C6A H6AB 109.9 . . ?
H6AA C6A H6AB 108.3 . . ?
C8A C7A C1A 109.22(9) . . ?
C8A C7A H7AA 109.8 . . ?
C1A C7A H7AA 109.8 . . ?
C8A C7A H7AB 109.8 . . ?
C1A C7A H7AB 109.8 . . ?
H7AA C7A H7AB 108.3 . . ?
C10A C8A C9A 110.32(9) . . ?
C10A C8A C7A 109.98(9) . . ?
C9A C8A C7A 109.12(9) . . ?
C10A C8A H8A 109.1 . . ?
C9A C8A H8A 109.1 . . ?
C7A C8A H8A 109.1 . . ?
C8A C9A C3A 109.19(9) . . ?
C8A C9A H9AA 109.8 . . ?
C3A C9A H9AA 109.8 . . ?
C8A C9A H9AB 109.8 . . ?
C3A C9A H9AB 109.8 . . ?
H9AA C9A H9AB 108.3 . . ?
C5A C10A C8A 108.59(9) . . ?
C5A C10A H10A 110.0 . . ?
C8A C10A H10A 110.0 . . ?
C5A C10A H10B 110.0 . . ?
C8A C10A H10B 110.0 . . ?
H10A C10A H10B 108.4 . . ?
C12A N11A C16A 118.66(10) . . ?
C12A N11A C1A 120.86(9) . . ?
C16A N11A C1A 120.39(9) . . ?
N11A C12A C13A 121.55(10) . . ?
N11A C12A H12A 119.2 . . ?
C13A C12A H12A 119.2 . . ?
C12A C13A C14A 120.93(10) . . ?
C12A C13A H13A 119.5 . . ?
C14A C13A H13A 119.5 . . ?
C15A C14A C13A 116.36(10) . . ?
C15A C14A C17A 121.76(10) . . ?
C13A C14A C17A 121.88(10) . . ?
C16A C15A C14A 120.60(10) . . ?
C16A C15A H15A 119.7 . . ?
C14A C15A H15A 119.7 . . ?
N11A C16A C15A 121.88(11) . . ?
N11A C16A H16A 119.1 . . ?
C15A C16A H16A 119.1 . . ?
C18A C17A C22A 118.29(10) . . ?
C18A C17A C14A 120.80(10) . . ?
C22A C17A C14A 120.91(10) . . ?
C19A C18A C17A 120.61(11) . . ?
C19A C18A H18A 119.7 . . ?
C17A C18A H18A 119.7 . . ?
C18A C19A C20A 121.34(11) . . ?
C18A C19A H19A 119.3 . . ?
C20A C19A H19A 119.3 . . ?
C19A C20A C21A 117.94(11) . . ?
C19A C20A C23A 120.84(11) . . ?
C21A C20A C23A 121.22(11) . . ?
C22A C21A C20A 121.44(11) . . ?
C22A C21A H21A 119.3 . . ?
C20A C21A H21A 119.3 . . ?
C21A C22A C17A 120.35(11) . . ?
C21A C22A H22A 119.8 . . ?
C17A C22A H22A 119.8 . . ?
C20A C23A H23A 109.5 . . ?
C20A C23A H23B 109.5 . . ?
H23A C23A H23B 109.5 . . ?
C20A C23A H23C 109.5 . . ?
H23A C23A H23C 109.5 . . ?
H23B C23A H23C 109.5 . . ?
N11B C1B C2B 108.06(9) . . ?
N11B C1B C7B 108.64(9) . . ?
C2B C1B C7B 110.32(9) . . ?
N11B C1B C6B 110.80(9) . . ?
C2B C1B C6B 109.60(9) . . ?
C7B C1B C6B 109.41(9) . . ?
C1B C2B C3B 108.64(9) . . ?
C1B C2B H2BA 110.0 . . ?
C3B C2B H2BA 110.0 . . ?
C1B C2B H2BB 110.0 . . ?
C3B C2B H2BB 110.0 . . ?
H2BA C2B H2BB 108.3 . . ?
C4B C3B C9B 109.92(10) . . ?
C4B C3B C2B 110.02(11) . . ?
C9B C3B C2B 108.97(10) . . ?
C4B C3B H3B 109.3 . . ?
C9B C3B H3B 109.3 . . ?
C2B C3B H3B 109.3 . . ?
C3B C4B C5B 109.43(10) . . ?
C3B C4B H4BA 109.8 . . ?
C5B C4B H4BA 109.8 . . ?
C3B C4B H4BB 109.8 . . ?
C5B C4B H4BB 109.8 . . ?
H4BA C4B H4BB 108.2 . . ?
C4B C5B C10B 109.87(10) . . ?
C4B C5B C6B 109.00(10) . . ?
C10B C5B C6B 109.74(10) . . ?
C4B C5B H5B 109.4 . . ?
C10B C5B H5B 109.4 . . ?
C6B C5B H5B 109.4 . . ?
C1B C6B C5B 109.31(9) . . ?
C1B C6B H6BA 109.8 . . ?
C5B C6B H6BA 109.8 . . ?
C1B C6B H6BB 109.8 . . ?
C5B C6B H6BB 109.8 . . ?
H6BA C6B H6BB 108.3 . . ?
C1B C7B C8B 108.60(9) . . ?
C1B C7B H7BA 110.0 . . ?
C8B C7B H7BA 110.0 . . ?
C1B C7B H7BB 110.0 . . ?
C8B C7B H7BB 110.0 . . ?
H7BA C7B H7BB 108.4 . . ?
C10B C8B C9B 109.95(10) . . ?
C10B C8B C7B 110.08(10) . . ?
C9B C8B C7B 109.32(9) . . ?
C10B C8B H8B 109.2 . . ?
C9B C8B H8B 109.2 . . ?
C7B C8B H8B 109.2 . . ?
C3B C9B C8B 109.37(10) . . ?
C3B C9B H9BA 109.8 . . ?
C8B C9B H9BA 109.8 . . ?
C3B C9B H9BB 109.8 . . ?
C8B C9B H9BB 109.8 . . ?
H9BA C9B H9BB 108.2 . . ?
C8B C10B C5B 108.90(10) . . ?
C8B C10B H10C 109.9 . . ?
C5B C10B H10C 109.9 . . ?
C8B C10B H10D 109.9 . . ?
C5B C10B H10D 109.9 . . ?
H10C C10B H10D 108.3 . . ?
C12B N11B C16B 119.45(10) . . ?
C12B N11B C1B 121.27(9) . . ?
C16B N11B C1B 119.25(9) . . ?
N11B C12B C13B 121.61(10) . . ?
N11B C12B H12B 119.2 . . ?
C13B C12B H12B 119.2 . . ?
C12B C13B C14B 120.26(11) . . ?
C12B C13B H13B 119.9 . . ?
C14B C13B H13B 119.9 . . ?
C13B C14B C15B 116.95(10) . . ?
C13B C14B C17B 121.00(10) . . ?
C15B C14B C17B 122.03(10) . . ?
C16B C15B C14B 120.96(11) . . ?
C16B C15B H15B 119.5 . . ?
C14B C15B H15B 119.5 . . ?
N11B C16B C15B 120.73(10) . . ?
N11B C16B H16B 119.6 . . ?
C15B C16B H16B 119.6 . . ?
C18B C17B C22B 118.63(10) . . ?
C18B C17B C14B 120.41(10) . . ?
C22B C17B C14B 120.95(10) . . ?
C19B C18B C17B 120.33(11) . . ?
C19B C18B H18B 119.8 . . ?
C17B C18B H18B 119.8 . . ?
C18B C19B C20B 121.14(11) . . ?
C18B C19B H19B 119.4 . . ?
C20B C19B H19B 119.4 . . ?
C19B C20B C21B 118.27(11) . . ?
C19B C20B C23B 121.14(11) . . ?
C21B C20B C23B 120.58(11) . . ?
C22B C21B C20B 120.94(11) . . ?
C22B C21B H21B 119.5 . . ?
C20B C21B H21B 119.5 . . ?
C21B C22B C17B 120.58(11) . . ?
C21B C22B H22B 119.7 . . ?
C17B C22B H22B 119.7 . . ?
C20B C23B H23D 109.5 . . ?
C20B C23B H23E 109.5 . . ?
H23D C23B H23E 109.5 . . ?
C20B C23B H23F 109.5 . . ?
H23D C23B H23F 109.5 . . ?
H23E C23B H23F 109.5 . . ?
H1W O1W H2W 109.3 . . ?

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
O1W H1W Cl2 0.89 2.25 3.1073(9) 161.2 . yes
O1W H2W Cl1 0.87 2.29 3.1298(9) 162.4 . yes

_refine_diff_density_max         0.305
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.039

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_dl077_kaleta
_database_code_depnum_ccdc_archive 'CCDC 2221721'
loop_
_audit_author_name
_audit_author_address
'Ivana Cisarova'
;Charles Univerzity
Czech Republic
;
_audit_update_record             
;
2022-11-23 deposited with the CCDC.	2023-08-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C22 H26 N), C2 H3 N, 2(Cl), 2(H2 O)'
_chemical_formula_sum            'C46 H59 Cl2 N3 O2'
_chemical_formula_weight         756.86
_chemical_compound_source        'synthesized by the authors'

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   10.1283(6)
_cell_length_b                   15.0534(8)
_cell_length_c                   15.6108(9)
_cell_angle_alpha                105.878(2)
_cell_angle_beta                 105.252(2)
_cell_angle_gamma                108.949(2)
_cell_volume                     1996.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9503
_cell_measurement_theta_min      2.2035
_cell_measurement_theta_max      27.4859

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless-yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_F_000             812
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.394
_exptl_crystal_size_mid          0.325
_exptl_crystal_size_min          0.216
_exptl_absorpt_coefficient_mu    0.205
_shelx_estimated_absorpt_T_min   0.924
_shelx_estimated_absorpt_T_max   0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS  micro-focus sealed tube'
_diffrn_radiation_monochromator  'Quazar Mo multilayer optic'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTONIII CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            101272
_diffrn_reflns_av_unetI/netI     0.0106
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.203
_diffrn_reflns_theta_max         27.506
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             9120
_reflns_number_gt                8704
_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       'Bruker Instrument Service vV6.2.15'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0427P)²+0.8823P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9120
_refine_ls_number_parameters     481
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0325
_refine_ls_wR_factor_ref         0.0901
_refine_ls_wR_factor_gt          0.0890
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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
Cl1 Cl 0.00560(3) 0.33797(2) 0.38441(2) 0.02742(7) Uani 1 1 d . . . . .
Cl2 Cl 0.24960(3) 0.36022(2) 0.76021(2) 0.02321(7) Uani 1 1 d . . . . .
C1A C 0.32488(11) -0.07258(8) 0.70975(7) 0.01708(19) Uani 1 1 d . . . . .
H1A H 0.240596 -0.105423 0.728726 0.020 Uiso 1 1 calc R U . . .
C2A C 0.44398(12) 0.02397(8) 0.79775(7) 0.0183(2) Uani 1 1 d . . . . .
H2A H 0.401580 0.075070 0.812798 0.022 Uiso 1 1 calc R U . . .
C3A C 0.48258(13) -0.00889(9) 0.88289(8) 0.0228(2) Uani 1 1 d . . . . .
H3AA H 0.557029 0.051726 0.942074 0.027 Uiso 1 1 calc R U . . .
H3AB H 0.389969 -0.039356 0.894592 0.027 Uiso 1 1 calc R U . . .
C4A C 0.54824(12) -0.08689(9) 0.86086(8) 0.0224(2) Uani 1 1 d . . . . .
H4A H 0.571976 -0.108112 0.916277 0.027 Uiso 1 1 calc R U . . .
C5A C 0.43142(13) -0.18013(9) 0.76949(8) 0.0250(2) Uani 1 1 d . . . . .
H5AA H 0.338082 -0.211530 0.780138 0.030 Uiso 1 1 calc R U . . .
H5AB H 0.472081 -0.231520 0.754844 0.030 Uiso 1 1 calc R U . . .
C6A C 0.39387(12) -0.14839(8) 0.68381(8) 0.0205(2) Uani 1 1 d . . . . .
H6A H 0.318219 -0.209792 0.624314 0.025 Uiso 1 1 calc R U . . .
C7A C 0.59098(12) 0.07206(8) 0.78282(8) 0.0206(2) Uani 1 1 d . . . . .
H7AA H 0.569797 0.095133 0.729204 0.025 Uiso 1 1 calc R U . . .
H7AB H 0.665891 0.132368 0.842117 0.025 Uiso 1 1 calc R U . . .
C8A C 0.65611(12) -0.00611(9) 0.75934(8) 0.0221(2) Uani 1 1 d . . . . .
H8A H 0.750474 0.025297 0.748557 0.026 Uiso 1 1 calc R U . . .
C9A C 0.53797(13) -0.09882(9) 0.66733(8) 0.0237(2) Uani 1 1 d . . . . .
H9AA H 0.513645 -0.076845 0.613216 0.028 Uiso 1 1 calc R U . . .
H9AB H 0.579562 -0.149154 0.649960 0.028 Uiso 1 1 calc R U . . .
C10A C 0.69275(12) -0.03957(9) 0.84386(8) 0.0237(2) Uani 1 1 d . . . . .
H10A H 0.734641 -0.090211 0.828957 0.028 Uiso 1 1 calc R U . . .
H10B H 0.769682 0.020190 0.902965 0.028 Uiso 1 1 calc R U . . .
N11A N 0.25747(9) -0.05144(7) 0.62310(6) 0.01626(17) Uani 1 1 d . . . . .
C12A C 0.15426(12) -0.13282(8) 0.54145(8) 0.0192(2) Uani 1 1 d . . . . .
H12A H 0.125288 -0.199500 0.541451 0.023 Uiso 1 1 calc R U . . .
C13A C 0.09050(12) -0.12082(8) 0.45844(7) 0.0190(2) Uani 1 1 d . . . . .
H13A H 0.019488 -0.179359 0.401833 0.023 Uiso 1 1 calc R U . . .
C14A C 0.12870(11) -0.02362(8) 0.45615(7) 0.01570(19) Uani 1 1 d . . . . .
C15A C 0.22855(12) 0.05914(8) 0.54372(7) 0.0188(2) Uani 1 1 d . . . . .
H15A H 0.254047 0.126866 0.546965 0.023 Uiso 1 1 calc R U . . .
C16A C 0.29027(12) 0.04367(8) 0.62520(7) 0.0188(2) Uani 1 1 d . . . . .
H16A H 0.357048 0.100963 0.683832 0.023 Uiso 1 1 calc R U . . .
C17A C 0.06490(11) -0.00923(8) 0.36689(7) 0.01560(19) Uani 1 1 d . . . . .
C18A C -0.04309(12) -0.09243(8) 0.28202(8) 0.0201(2) Uani 1 1 d . . . . .
H18A H -0.078651 -0.159169 0.281887 0.024 Uiso 1 1 calc R U . . .
C19A C -0.09849(12) -0.07803(8) 0.19812(8) 0.0217(2) Uani 1 1 d . . . . .
H19A H -0.172354 -0.135315 0.141364 0.026 Uiso 1 1 calc R U . . .
C20A C -0.04836(12) 0.01840(8) 0.19519(7) 0.0191(2) Uani 1 1 d . . . . .
C21A C 0.05539(13) 0.10135(8) 0.28043(8) 0.0223(2) Uani 1 1 d . . . . .
H21A H 0.088376 0.168226 0.280795 0.027 Uiso 1 1 calc R U . . .
C22A C 0.11139(13) 0.08808(8) 0.36479(8) 0.0209(2) Uani 1 1 d . . . . .
H22A H 0.182361 0.145910 0.421991 0.025 Uiso 1 1 calc R U . . .
C23A C -0.10279(14) 0.03242(10) 0.10249(8) 0.0257(2) Uani 1 1 d . . . . .
H23A H -0.122033 0.093528 0.115586 0.039 Uiso 1 1 calc R U . . .
H23B H -0.196482 -0.027522 0.056608 0.039 Uiso 1 1 calc R U . . .
H23C H -0.025293 0.040390 0.074930 0.039 Uiso 1 1 calc R U . . .
C1B C 0.64085(12) 0.54336(8) 0.79196(7) 0.01720(19) Uani 1 1 d . . . . .
H1B H 0.590446 0.467916 0.773416 0.021 Uiso 1 1 calc R U . . .
C2B C 0.60878(12) 0.59510(8) 0.87905(7) 0.0193(2) Uani 1 1 d . . . . .
H2B H 0.498327 0.578090 0.858348 0.023 Uiso 1 1 calc R U . . .
C3B C 0.65440(13) 0.55261(9) 0.95535(8) 0.0236(2) Uani 1 1 d . . . . .
H3BA H 0.633082 0.582991 1.011964 0.028 Uiso 1 1 calc R U . . .
H3BB H 0.594319 0.477638 0.928108 0.028 Uiso 1 1 calc R U . . .
C4B C 0.82321(13) 0.57788(9) 0.98685(8) 0.0230(2) Uani 1 1 d . . . . .
H4B H 0.852163 0.549307 1.035844 0.028 Uiso 1 1 calc R U . . .
C5B C 0.85437(14) 0.53041(9) 0.89840(8) 0.0249(2) Uani 1 1 d . . . . .
H5BA H 0.794662 0.455342 0.869890 0.030 Uiso 1 1 calc R U . . .
H5BB H 0.962989 0.545108 0.918344 0.030 Uiso 1 1 calc R U . . .
C6B C 0.81125(12) 0.57457(8) 0.82230(8) 0.0192(2) Uani 1 1 d . . . . .
H6B H 0.833409 0.544393 0.765242 0.023 Uiso 1 1 calc R U . . .
C7B C 0.70047(13) 0.71124(8) 0.92136(8) 0.0217(2) Uani 1 1 d . . . . .
H7BA H 0.672891 0.738269 0.871578 0.026 Uiso 1 1 calc R U . . .
H7BB H 0.676734 0.743214 0.976188 0.026 Uiso 1 1 calc R U . . .
C8B C 0.86996(12) 0.73791(8) 0.95600(8) 0.0217(2) Uani 1 1 d . . . . .
H8B H 0.929369 0.813828 0.985036 0.026 Uiso 1 1 calc R U . . .
C9B C 0.90447(12) 0.69143(9) 0.86881(8) 0.0219(2) Uani 1 1 d . . . . .
H9BA H 1.013770 0.708024 0.889823 0.026 Uiso 1 1 calc R U . . .
H9BB H 0.879197 0.720950 0.820784 0.026 Uiso 1 1 calc R U . . .
C10B C 0.91458(13) 0.69412(9) 1.03122(8) 0.0237(2) Uani 1 1 d . . . . .
H10C H 1.024124 0.711437 1.052547 0.028 Uiso 1 1 calc R U . . .
H10D H 0.894296 0.724443 1.088333 0.028 Uiso 1 1 calc R U . . .
N11B N 0.57179(10) 0.56493(6) 0.70617(6) 0.01619(17) Uani 1 1 d . . . . .
C12B C 0.65012(12) 0.60524(8) 0.65766(7) 0.0181(2) Uani 1 1 d . . . . .
H12B H 0.754199 0.619113 0.675934 0.022 Uiso 1 1 calc R U . . .
C13B C 0.58140(12) 0.62655(8) 0.58211(7) 0.0184(2) Uani 1 1 d . . . . .
H13B H 0.639500 0.656335 0.550122 0.022 Uiso 1 1 calc R U . . .
C14B C 0.42715(11) 0.60503(7) 0.55159(7) 0.01616(19) Uani 1 1 d . . . . .
C15B C 0.34733(12) 0.55664(8) 0.59915(8) 0.0204(2) Uani 1 1 d . . . . .
H15B H 0.241329 0.536628 0.578876 0.025 Uiso 1 1 calc R U . . .
C16B C 0.42105(12) 0.53790(8) 0.67484(8) 0.0195(2) Uani 1 1 d . . . . .
H16B H 0.364629 0.505061 0.706026 0.023 Uiso 1 1 calc R U . . .
C17B C 0.35292(11) 0.63086(8) 0.47317(7) 0.01681(19) Uani 1 1 d . . . . .
C18B C 0.43302(12) 0.67159(8) 0.42178(8) 0.0208(2) Uani 1 1 d . . . . .
H18B H 0.534796 0.680559 0.436145 0.025 Uiso 1 1 calc R U . . .
C19B C 0.36495(13) 0.69893(9) 0.35013(8) 0.0223(2) Uani 1 1 d . . . . .
H19B H 0.420880 0.726308 0.315975 0.027 Uiso 1 1 calc R U . . .
C20B C 0.21592(12) 0.68690(8) 0.32742(8) 0.0201(2) Uani 1 1 d . . . . .
C21B C 0.13589(12) 0.64505(8) 0.37766(8) 0.0211(2) Uani 1 1 d . . . . .
H21B H 0.033741 0.635429 0.362541 0.025 Uiso 1 1 calc R U . . .
C22B C 0.20245(12) 0.61710(8) 0.44944(8) 0.0201(2) Uani 1 1 d . . . . .
H22B H 0.145519 0.588514 0.482558 0.024 Uiso 1 1 calc R U . . .
C23B C 0.14453(14) 0.71877(10) 0.25094(9) 0.0267(2) Uani 1 1 d . . . . .
H23D H 0.034587 0.678126 0.222746 0.040 Uiso 1 1 calc R U . . .
H23E H 0.184814 0.707607 0.200330 0.040 Uiso 1 1 calc R U . . .
H23F H 0.167697 0.791339 0.279928 0.040 Uiso 1 1 calc R U . . .
N1S N 0.63941(19) 0.29175(14) 1.01507(11) 0.0629(4) Uani 1 1 d . . . . .
C1S C 0.71907(16) 0.34434(11) 1.09246(10) 0.0360(3) Uani 1 1 d . . . . .
C2S C 0.82045(16) 0.41275(11) 1.19120(10) 0.0347(3) Uani 1 1 d . . . . .
H2S1 H 0.796748 0.471468 1.210604 0.052 Uiso 1 1 calc R U . . .
H2S2 H 0.925302 0.436585 1.195751 0.052 Uiso 1 1 calc R U . . .
H2S3 H 0.807822 0.376416 1.233960 0.052 Uiso 1 1 calc R U . . .
O1W O 0.21499(9) 0.29581(6) 0.54293(6) 0.02707(18) Uani 1 1 d . . . . .
H11W H 0.156409 0.316878 0.511613 0.041 Uiso 1 1 d R U . . .
H12W H 0.214509 0.316978 0.601413 0.041 Uiso 1 1 d R U . . .
O2W O 0.47020(11) 0.25638(7) 0.80812(7) 0.0326(2) Uani 1 1 d . . . . .
H21W H 0.416313 0.290828 0.805547 0.049 Uiso 1 1 d R U . . .
H22W H 0.513813 0.275126 0.870547 0.049 Uiso 1 1 d 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
C1A N11A 1.5126(12) . ?
C1A C2A 1.5336(14) . ?
C1A C6A 1.5390(14) . ?
C1A H1A 1.0000 . ?
C2A C7A 1.5395(15) . ?
C2A C3A 1.5414(14) . ?
C2A H2A 1.0000 . ?
C3A C4A 1.5315(16) . ?
C3A H3AA 0.9900 . ?
C3A H3AB 0.9900 . ?
C4A C5A 1.5305(16) . ?
C4A C10A 1.5332(16) . ?
C4A H4A 1.0000 . ?
C5A C6A 1.5369(15) . ?
C5A H5AA 0.9900 . ?
C5A H5AB 0.9900 . ?
C6A C9A 1.5325(16) . ?
C6A H6A 1.0000 . ?
C7A C8A 1.5328(15) . ?
C7A H7AA 0.9900 . ?
C7A H7AB 0.9900 . ?
C8A C9A 1.5352(16) . ?
C8A C10A 1.5362(15) . ?
C8A H8A 1.0000 . ?
C9A H9AA 0.9900 . ?
C9A H9AB 0.9900 . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
N11A C16A 1.3494(13) . ?
N11A C12A 1.3531(13) . ?
C12A C13A 1.3756(14) . ?
C12A H12A 0.9500 . ?
C13A C14A 1.4001(14) . ?
C13A H13A 0.9500 . ?
C14A C15A 1.4023(14) . ?
C14A C17A 1.4794(13) . ?
C15A C16A 1.3788(14) . ?
C15A H15A 0.9500 . ?
C16A H16A 0.9500 . ?
C17A C22A 1.3982(14) . ?
C17A C18A 1.4000(14) . ?
C18A C19A 1.3875(14) . ?
C18A H18A 0.9500 . ?
C19A C20A 1.3917(15) . ?
C19A H19A 0.9500 . ?
C20A C21A 1.3918(15) . ?
C20A C23A 1.5052(14) . ?
C21A C22A 1.3857(15) . ?
C21A H21A 0.9500 . ?
C22A H22A 0.9500 . ?
C23A H23A 0.9800 . ?
C23A H23B 0.9800 . ?
C23A H23C 0.9800 . ?
C1B N11B 1.5104(12) . ?
C1B C6B 1.5314(14) . ?
C1B C2B 1.5420(14) . ?
C1B H1B 1.0000 . ?
C2B C7B 1.5317(15) . ?
C2B C3B 1.5364(14) . ?
C2B H2B 1.0000 . ?
C3B C4B 1.5306(16) . ?
C3B H3BA 0.9900 . ?
C3B H3BB 0.9900 . ?
C4B C10B 1.5316(16) . ?
C4B C5B 1.5338(16) . ?
C4B H4B 1.0000 . ?
C5B C6B 1.5466(14) . ?
C5B H5BA 0.9900 . ?
C5B H5BB 0.9900 . ?
C6B C9B 1.5412(15) . ?
C6B H6B 1.0000 . ?
C7B C8B 1.5315(15) . ?
C7B H7BA 0.9900 . ?
C7B H7BB 0.9900 . ?
C8B C9B 1.5338(16) . ?
C8B C10B 1.5347(14) . ?
C8B H8B 1.0000 . ?
C9B H9BA 0.9900 . ?
C9B H9BB 0.9900 . ?
C10B H10C 0.9900 . ?
C10B H10D 0.9900 . ?
N11B C12B 1.3513(13) . ?
N11B C16B 1.3529(13) . ?
C12B C13B 1.3778(14) . ?
C12B H12B 0.9500 . ?
C13B C14B 1.4028(14) . ?
C13B H13B 0.9500 . ?
C14B C15B 1.4017(14) . ?
C14B C17B 1.4769(14) . ?
C15B C16B 1.3742(14) . ?
C15B H15B 0.9500 . ?
C16B H16B 0.9500 . ?
C17B C22B 1.3995(14) . ?
C17B C18B 1.4022(15) . ?
C18B C19B 1.3880(15) . ?
C18B H18B 0.9500 . ?
C19B C20B 1.3938(15) . ?
C19B H19B 0.9500 . ?
C20B C21B 1.3937(15) . ?
C20B C23B 1.5043(14) . ?
C21B C22B 1.3898(15) . ?
C21B H21B 0.9500 . ?
C22B H22B 0.9500 . ?
C23B H23D 0.9800 . ?
C23B H23E 0.9800 . ?
C23B H23F 0.9800 . ?
N1S C1S 1.134(2) . ?
C1S C2S 1.450(2) . ?
C2S H2S1 0.9800 . ?
C2S H2S2 0.9800 . ?
C2S H2S3 0.9800 . ?
O1W H11W 0.8637 . ?
O1W H12W 0.8827 . ?
O2W H21W 0.8673 . ?
O2W H22W 0.8755 . ?

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
N11A C1A C2A 113.57(8) . . ?
N11A C1A C6A 110.86(8) . . ?
C2A C1A C6A 109.53(8) . . ?
N11A C1A H1A 107.5 . . ?
C2A C1A H1A 107.5 . . ?
C6A C1A H1A 107.5 . . ?
C1A C2A C7A 112.36(8) . . ?
C1A C2A C3A 106.77(9) . . ?
C7A C2A C3A 107.92(8) . . ?
C1A C2A H2A 109.9 . . ?
C7A C2A H2A 109.9 . . ?
C3A C2A H2A 109.9 . . ?
C4A C3A C2A 110.40(9) . . ?
C4A C3A H3AA 109.6 . . ?
C2A C3A H3AA 109.6 . . ?
C4A C3A H3AB 109.6 . . ?
C2A C3A H3AB 109.6 . . ?
H3AA C3A H3AB 108.1 . . ?
C5A C4A C3A 108.81(9) . . ?
C5A C4A C10A 109.15(10) . . ?
C3A C4A C10A 109.74(9) . . ?
C5A C4A H4A 109.7 . . ?
C3A C4A H4A 109.7 . . ?
C10A C4A H4A 109.7 . . ?
C4A C5A C6A 110.17(9) . . ?
C4A C5A H5AA 109.6 . . ?
C6A C5A H5AA 109.6 . . ?
C4A C5A H5AB 109.6 . . ?
C6A C5A H5AB 109.6 . . ?
H5AA C5A H5AB 108.1 . . ?
C9A C6A C5A 110.01(9) . . ?
C9A C6A C1A 111.10(9) . . ?
C5A C6A C1A 106.66(9) . . ?
C9A C6A H6A 109.7 . . ?
C5A C6A H6A 109.7 . . ?
C1A C6A H6A 109.7 . . ?
C8A C7A C2A 110.11(9) . . ?
C8A C7A H7AA 109.6 . . ?
C2A C7A H7AA 109.6 . . ?
C8A C7A H7AB 109.6 . . ?
C2A C7A H7AB 109.6 . . ?
H7AA C7A H7AB 108.2 . . ?
C7A C8A C9A 108.65(9) . . ?
C7A C8A C10A 109.47(9) . . ?
C9A C8A C10A 109.89(9) . . ?
C7A C8A H8A 109.6 . . ?
C9A C8A H8A 109.6 . . ?
C10A C8A H8A 109.6 . . ?
C6A C9A C8A 109.92(9) . . ?
C6A C9A H9AA 109.7 . . ?
C8A C9A H9AA 109.7 . . ?
C6A C9A H9AB 109.7 . . ?
C8A C9A H9AB 109.7 . . ?
H9AA C9A H9AB 108.2 . . ?
C4A C10A C8A 109.55(9) . . ?
C4A C10A H10A 109.8 . . ?
C8A C10A H10A 109.8 . . ?
C4A C10A H10B 109.8 . . ?
C8A C10A H10B 109.8 . . ?
H10A C10A H10B 108.2 . . ?
C16A N11A C12A 119.32(9) . . ?
C16A N11A C1A 123.23(9) . . ?
C12A N11A C1A 117.38(8) . . ?
N11A C12A C13A 121.26(10) . . ?
N11A C12A H12A 119.4 . . ?
C13A C12A H12A 119.4 . . ?
C12A C13A C14A 120.97(10) . . ?
C12A C13A H13A 119.5 . . ?
C14A C13A H13A 119.5 . . ?
C13A C14A C15A 116.10(9) . . ?
C13A C14A C17A 121.83(9) . . ?
C15A C14A C17A 122.07(9) . . ?
C16A C15A C14A 120.97(10) . . ?
C16A C15A H15A 119.5 . . ?
C14A C15A H15A 119.5 . . ?
N11A C16A C15A 121.14(9) . . ?
N11A C16A H16A 119.4 . . ?
C15A C16A H16A 119.4 . . ?
C22A C17A C18A 118.04(9) . . ?
C22A C17A C14A 120.84(9) . . ?
C18A C17A C14A 121.12(9) . . ?
C19A C18A C17A 120.42(10) . . ?
C19A C18A H18A 119.8 . . ?
C17A C18A H18A 119.8 . . ?
C18A C19A C20A 121.52(10) . . ?
C18A C19A H19A 119.2 . . ?
C20A C19A H19A 119.2 . . ?
C19A C20A C21A 117.89(10) . . ?
C19A C20A C23A 121.09(10) . . ?
C21A C20A C23A 121.01(10) . . ?
C22A C21A C20A 121.14(10) . . ?
C22A C21A H21A 119.4 . . ?
C20A C21A H21A 119.4 . . ?
C21A C22A C17A 120.93(10) . . ?
C21A C22A H22A 119.5 . . ?
C17A C22A H22A 119.5 . . ?
C20A C23A H23A 109.5 . . ?
C20A C23A H23B 109.5 . . ?
H23A C23A H23B 109.5 . . ?
C20A C23A H23C 109.5 . . ?
H23A C23A H23C 109.5 . . ?
H23B C23A H23C 109.5 . . ?
N11B C1B C6B 113.95(8) . . ?
N11B C1B C2B 110.86(8) . . ?
C6B C1B C2B 109.55(8) . . ?
N11B C1B H1B 107.4 . . ?
C6B C1B H1B 107.4 . . ?
C2B C1B H1B 107.4 . . ?
C7B C2B C3B 109.80(9) . . ?
C7B C2B C1B 110.85(9) . . ?
C3B C2B C1B 107.37(9) . . ?
C7B C2B H2B 109.6 . . ?
C3B C2B H2B 109.6 . . ?
C1B C2B H2B 109.6 . . ?
C4B C3B C2B 109.81(9) . . ?
C4B C3B H3BA 109.7 . . ?
C2B C3B H3BA 109.7 . . ?
C4B C3B H3BB 109.7 . . ?
C2B C3B H3BB 109.7 . . ?
H3BA C3B H3BB 108.2 . . ?
C3B C4B C10B 109.02(9) . . ?
C3B C4B C5B 109.06(9) . . ?
C10B C4B C5B 110.02(10) . . ?
C3B C4B H4B 109.6 . . ?
C10B C4B H4B 109.6 . . ?
C5B C4B H4B 109.6 . . ?
C4B C5B C6B 110.14(9) . . ?
C4B C5B H5BA 109.6 . . ?
C6B C5B H5BA 109.6 . . ?
C4B C5B H5BB 109.6 . . ?
C6B C5B H5BB 109.6 . . ?
H5BA C5B H5BB 108.1 . . ?
C1B C6B C9B 112.45(9) . . ?
C1B C6B C5B 105.92(9) . . ?
C9B C6B C5B 108.55(9) . . ?
C1B C6B H6B 109.9 . . ?
C9B C6B H6B 109.9 . . ?
C5B C6B H6B 109.9 . . ?
C8B C7B C2B 109.84(9) . . ?
C8B C7B H7BA 109.7 . . ?
C2B C7B H7BA 109.7 . . ?
C8B C7B H7BB 109.7 . . ?
C2B C7B H7BB 109.7 . . ?
H7BA C7B H7BB 108.2 . . ?
C7B C8B C9B 108.50(9) . . ?
C7B C8B C10B 110.65(9) . . ?
C9B C8B C10B 109.06(9) . . ?
C7B C8B H8B 109.5 . . ?
C9B C8B H8B 109.5 . . ?
C10B C8B H8B 109.5 . . ?
C8B C9B C6B 110.01(9) . . ?
C8B C9B H9BA 109.7 . . ?
C6B C9B H9BA 109.7 . . ?
C8B C9B H9BB 109.7 . . ?
C6B C9B H9BB 109.7 . . ?
H9BA C9B H9BB 108.2 . . ?
C4B C10B C8B 109.53(9) . . ?
C4B C10B H10C 109.8 . . ?
C8B C10B H10C 109.8 . . ?
C4B C10B H10D 109.8 . . ?
C8B C10B H10D 109.8 . . ?
H10C C10B H10D 108.2 . . ?
C12B N11B C16B 119.04(9) . . ?
C12B N11B C1B 123.97(9) . . ?
C16B N11B C1B 116.94(8) . . ?
N11B C12B C13B 121.03(9) . . ?
N11B C12B H12B 119.5 . . ?
C13B C12B H12B 119.5 . . ?
C12B C13B C14B 121.17(9) . . ?
C12B C13B H13B 119.4 . . ?
C14B C13B H13B 119.4 . . ?
C15B C14B C13B 116.11(9) . . ?
C15B C14B C17B 121.98(9) . . ?
C13B C14B C17B 121.90(9) . . ?
C16B C15B C14B 120.58(10) . . ?
C16B C15B H15B 119.7 . . ?
C14B C15B H15B 119.7 . . ?
N11B C16B C15B 121.80(10) . . ?
N11B C16B H16B 119.1 . . ?
C15B C16B H16B 119.1 . . ?
C22B C17B C18B 118.42(9) . . ?
C22B C17B C14B 121.07(9) . . ?
C18B C17B C14B 120.50(9) . . ?
C19B C18B C17B 120.59(10) . . ?
C19B C18B H18B 119.7 . . ?
C17B C18B H18B 119.7 . . ?
C18B C19B C20B 121.12(10) . . ?
C18B C19B H19B 119.4 . . ?
C20B C19B H19B 119.4 . . ?
C21B C20B C19B 118.16(10) . . ?
C21B C20B C23B 121.27(10) . . ?
C19B C20B C23B 120.56(10) . . ?
C22B C21B C20B 121.35(10) . . ?
C22B C21B H21B 119.3 . . ?
C20B C21B H21B 119.3 . . ?
C21B C22B C17B 120.34(10) . . ?
C21B C22B H22B 119.8 . . ?
C17B C22B H22B 119.8 . . ?
C20B C23B H23D 109.5 . . ?
C20B C23B H23E 109.5 . . ?
H23D C23B H23E 109.5 . . ?
C20B C23B H23F 109.5 . . ?
H23D C23B H23F 109.5 . . ?
H23E C23B H23F 109.5 . . ?
N1S C1S C2S 179.19(17) . . ?
C1S C2S H2S1 109.5 . . ?
C1S C2S H2S2 109.5 . . ?
H2S1 C2S H2S2 109.5 . . ?
C1S C2S H2S3 109.5 . . ?
H2S1 C2S H2S3 109.5 . . ?
H2S2 C2S H2S3 109.5 . . ?
H11W O1W H12W 103.3 . . ?
H21W O2W H22W 101.3 . . ?

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
O1W H11W Cl1 0.86 2.33 3.1618(9) 161.0 . yes
O1W H12W Cl2 0.88 2.28 3.1499(9) 168.5 . yes
O2W H21W Cl2 0.87 2.32 3.1661(10) 166.6 . yes
O2W H22W N1S 0.88 2.18 3.0349(18) 165.9 . yes

_refine_diff_density_max         0.352
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.040

