# Electronic Supplementary Material (ESI) for Materials Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_mw340
_database_code_depnum_ccdc_archive 'CCDC 2024261'
loop_
_audit_author_name
_audit_author_address
'Duane Hean'
;University of British Columbia
Canada
;
_audit_update_record             
;
2020-08-19 deposited with the CCDC.	2021-07-28 downloaded from the CCDC.
;
_audit_creation_date             2019-10-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H21 N2, B F4'
_chemical_formula_sum            'C21 H21 B F4 N2'
_chemical_formula_weight         388.21
_chemical_melting_point          ?
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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   15.42(7)
_cell_length_b                   9.79(5)
_cell_length_c                   25.07(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3786(30)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3878
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      26.517
_cell_measurement_theta_min      2.623
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.962
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1012 before and 0.0514 after correction. The Ratio of minimum to maximum transmission is 0.8856. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.367
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_av_unetI/netI     0.0641
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            15716
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.444
_diffrn_reflns_theta_min         1.625
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2437
_reflns_number_total             3810
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3810
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0912
_refine_ls_R_factor_gt           0.0453
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0388P)²+1.0984P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0893
_refine_ls_wR_factor_ref         0.1063
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C17(H17),
 C18(H18), C19(H19), C20(H20), C21(H21)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
N1 N 0.17369(10) 0.35620(16) 0.76064(7) 0.0187(4) Uani 1 1 d . . . . .
N2 N 0.45087(10) 0.51273(16) 0.58493(7) 0.0180(4) Uani 1 1 d . . . . .
C1 C 0.09811(12) 0.30429(19) 0.73647(8) 0.0154(4) Uani 1 1 d . . . . .
C2 C 0.06328(13) 0.33202(19) 0.68580(9) 0.0186(5) Uani 1 1 d . . . . .
H2 H 0.092871 0.388822 0.661049 0.022 Uiso 1 1 calc R . . . .
C3 C -0.01675(13) 0.2726(2) 0.67323(9) 0.0216(5) Uani 1 1 d . . . . .
H3 H -0.042401 0.291396 0.639563 0.026 Uiso 1 1 calc R . . . .
C4 C -0.06035(13) 0.1856(2) 0.70923(9) 0.0234(5) Uani 1 1 d . . . . .
H4 H -0.114373 0.146425 0.699367 0.028 Uiso 1 1 calc R . . . .
C5 C -0.02499(13) 0.1567(2) 0.75900(9) 0.0217(5) Uani 1 1 d . . . . .
H5 H -0.054307 0.097549 0.783037 0.026 Uiso 1 1 calc R . . . .
C6 C 0.05517(12) 0.21639(19) 0.77338(8) 0.0168(5) Uani 1 1 d . . . . .
C7 C 0.10738(13) 0.2133(2) 0.82178(9) 0.0191(5) Uani 1 1 d . . . . .
C8 C 0.09924(14) 0.1470(2) 0.87148(9) 0.0245(5) Uani 1 1 d . . . . .
H8 H 0.053141 0.084644 0.877721 0.029 Uiso 1 1 calc R . . . .
C9 C 0.16011(15) 0.1744(2) 0.91143(10) 0.0308(6) Uani 1 1 d . . . . .
H9 H 0.155580 0.129764 0.944956 0.037 Uiso 1 1 calc R . . . .
C10 C 0.22825(14) 0.2679(2) 0.90237(9) 0.0306(6) Uani 1 1 d . . . . .
H10 H 0.267642 0.287319 0.930503 0.037 Uiso 1 1 calc R . . . .
C11 C 0.23933(14) 0.3326(2) 0.85327(9) 0.0260(5) Uani 1 1 d . . . . .
H11 H 0.286024 0.394083 0.847433 0.031 Uiso 1 1 calc R . . . .
C12 C 0.17905(13) 0.3038(2) 0.81267(8) 0.0193(5) Uani 1 1 d . . . . .
C13 C 0.23629(13) 0.4483(2) 0.73455(9) 0.0214(5) Uani 1 1 d . . . . .
H13A H 0.276459 0.485170 0.761778 0.026 Uiso 1 1 calc R . . . .
H13B H 0.204581 0.526207 0.718627 0.026 Uiso 1 1 calc R . . . .
C14 C 0.28917(12) 0.3765(2) 0.69077(9) 0.0189(5) Uani 1 1 d . . . . .
H14A H 0.249395 0.341025 0.663042 0.023 Uiso 1 1 calc R . . . .
H14B H 0.320669 0.298026 0.706407 0.023 Uiso 1 1 calc R . . . .
C15 C 0.35484(13) 0.4760(2) 0.66497(9) 0.0217(5) Uani 1 1 d . . . . .
H15A H 0.326587 0.565252 0.658549 0.026 Uiso 1 1 calc R . . . .
H15B H 0.404264 0.490688 0.689508 0.026 Uiso 1 1 calc R . . . .
C16 C 0.38796(13) 0.4174(2) 0.61199(9) 0.0217(5) Uani 1 1 d . . . . .
H16A H 0.416871 0.328838 0.618737 0.026 Uiso 1 1 calc R . . . .
H16B H 0.338106 0.400599 0.587994 0.026 Uiso 1 1 calc R . . . .
C17 C 0.53641(13) 0.4812(2) 0.58379(9) 0.0208(5) Uani 1 1 d . . . . .
H17 H 0.556725 0.401937 0.601736 0.025 Uiso 1 1 calc R . . . .
C18 C 0.59464(13) 0.5642(2) 0.55647(9) 0.0228(5) Uani 1 1 d . . . . .
H18 H 0.654424 0.541076 0.555221 0.027 Uiso 1 1 calc R . . . .
C19 C 0.56471(13) 0.6816(2) 0.53096(9) 0.0215(5) Uani 1 1 d . . . . .
H19 H 0.603630 0.738252 0.511645 0.026 Uiso 1 1 calc R . . . .
C20 C 0.47673(13) 0.7149(2) 0.53416(9) 0.0220(5) Uani 1 1 d . . . . .
H20 H 0.455672 0.796184 0.518007 0.026 Uiso 1 1 calc R . . . .
C21 C 0.42041(13) 0.6288(2) 0.56103(9) 0.0208(5) Uani 1 1 d . . . . .
H21 H 0.360433 0.650379 0.562857 0.025 Uiso 1 1 calc R . . . .
F1 F 0.31651(8) 0.90377(12) 0.56191(6) 0.0396(4) Uani 1 1 d . . . . .
F2 F 0.42585(8) 1.05722(14) 0.54644(6) 0.0433(4) Uani 1 1 d . . . . .
F3 F 0.28593(8) 1.11601(15) 0.52827(6) 0.0486(4) Uani 1 1 d . . . . .
F4 F 0.33045(11) 1.09167(14) 0.61442(6) 0.0547(5) Uani 1 1 d . . . . .
B1 B 0.33970(15) 1.0420(2) 0.56256(11) 0.0220(6) Uani 1 1 d . . . . .


_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 C1 1.409(5) . ?
N1 C12 1.404(6) . ?
N1 C13 1.474(5) . ?
N2 C16 1.507(5) . ?
N2 C17 1.355(6) . ?
N2 C21 1.368(5) . ?
C1 C2 1.405(6) . ?
C1 C6 1.427(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.401(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.412(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.391(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.414(6) . ?
C6 C7 1.456(6) . ?
C7 C8 1.411(6) . ?
C7 C12 1.435(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.399(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.412(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.395(6) . ?
C11 H11 0.9500 . ?
C11 C12 1.407(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.538(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.547(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.534(6) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17 0.9500 . ?
C17 C18 1.392(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.394(6) . ?
C19 H19 0.9500 . ?
C19 C20 1.398(7) . ?
C20 H20 0.9500 . ?
C20 C21 1.386(5) . ?
C21 H21 0.9500 . ?
F1 B1 1.400(7) . ?
F2 B1 1.397(6) . ?
F3 B1 1.397(5) . ?
F4 B1 1.395(6) . ?

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
C1 N1 C13 124.9(3) . . ?
C12 N1 C1 108.4(2) . . ?
C12 N1 C13 126.7(2) . . ?
C17 N2 C16 119.7(3) . . ?
C17 N2 C21 120.96(18) . . ?
C21 N2 C16 119.4(3) . . ?
N1 C1 C6 108.8(3) . . ?
C2 C1 N1 129.4(2) . . ?
C2 C1 C6 121.7(3) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 C1 117.4(2) . . ?
C3 C2 H2 121.3 . . ?
C2 C3 H3 119.1 . . ?
C2 C3 C4 121.8(3) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.6(3) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.4 . . ?
C4 C5 C6 119.1(2) . . ?
C6 C5 H5 120.4 . . ?
C1 C6 C7 107.2(3) . . ?
C5 C6 C1 119.3(3) . . ?
C5 C6 C7 133.4(2) . . ?
C8 C7 C6 134.1(3) . . ?
C8 C7 C12 119.6(2) . . ?
C12 C7 C6 106.3(3) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 C7 119.0(3) . . ?
C9 C8 H8 120.5 . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.6(3) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 119.1 . . ?
C11 C10 C9 121.8(2) . . ?
C11 C10 H10 119.1 . . ?
C10 C11 H11 121.1 . . ?
C10 C11 C12 117.8(3) . . ?
C12 C11 H11 121.1 . . ?
N1 C12 C7 109.2(2) . . ?
N1 C12 C11 129.6(3) . . ?
C11 C12 C7 121.2(3) . . ?
N1 C13 H13A 109.1 . . ?
N1 C13 H13B 109.1 . . ?
N1 C13 C14 112.6(3) . . ?
H13A C13 H13B 107.8 . . ?
C14 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.4 . . ?
C13 C14 C15 110.9(3) . . ?
H14A C14 H14B 108.0 . . ?
C15 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
C14 C15 H15A 109.6 . . ?
C14 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
C16 C15 C14 110.2(3) . . ?
C16 C15 H15A 109.6 . . ?
C16 C15 H15B 109.6 . . ?
N2 C16 C15 111.9(3) . . ?
N2 C16 H16A 109.2 . . ?
N2 C16 H16B 109.2 . . ?
C15 C16 H16A 109.2 . . ?
C15 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
N2 C17 H17 119.8 . . ?
N2 C17 C18 120.3(3) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 120.2 . . ?
C17 C18 C19 119.6(3) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 120.4 . . ?
C18 C19 C20 119.2(2) . . ?
C20 C19 H19 120.4 . . ?
C19 C20 H20 120.2 . . ?
C21 C20 C19 119.6(3) . . ?
C21 C20 H20 120.2 . . ?
N2 C21 C20 120.2(3) . . ?
N2 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
F2 B1 F1 110.05(19) . . ?
F2 B1 F3 109.3(3) . . ?
F3 B1 F1 110.1(3) . . ?
F4 B1 F1 108.8(2) . . ?
F4 B1 F2 109.2(2) . . ?
F4 B1 F3 109.4(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mw368_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2024262'
loop_
_audit_author_name
_audit_author_address
'Duane Hean'
;University of British Columbia
Canada
;
_audit_update_record             
;
2020-08-19 deposited with the CCDC.	2021-07-28 downloaded from the CCDC.
;
_audit_creation_date             2019-10-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H21 N2, Cl, 0.78(H2 O), H1.55 O0.22'
_chemical_formula_sum            'C21 H24.11 Cl N2 O'
_chemical_formula_weight         355.98
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   15.316(19)
_cell_length_b                   9.637(14)
_cell_length_c                   25.52(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3767(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9696
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      26.44
_cell_measurement_theta_min      2.62
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.932
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6932
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0776 before and 0.0498 after correction. The Ratio of minimum to maximum transmission is 0.9300. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1513
_exptl_crystal_size_max          0.333
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            62541
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.537
_diffrn_reflns_theta_min         1.596
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3461
_reflns_number_total             3899
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         1.438
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.220
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3899
_refine_ls_number_restraints     345
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0828
_refine_ls_restrained_S_all      1.168
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0458P)²+13.8289P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1975
_refine_ls_wR_factor_ref         0.2017
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
Uanis(O1B) = Uanis(O1A)
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(Cl1B)=1-FVAR(1)
 Sof(Cl1A)=FVAR(1)
 Sof(O1B)=1-FVAR(2)
 Sof(O1A)=Sof(H1AA)=Sof(H1AB)=FVAR(2)
 Sof(H1BA)=Sof(H1BB)=FVAR(3)
5.a Free rotating group:
 O1A(H1AA,H1AB), O1B(H1BA,H1BB)
5.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C17(H17),
 C18(H18), C19(H19), C20(H20), C21(H21)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
N1 N 0.16839(18) 0.4034(3) 0.75194(11) 0.0165(6) Uani 1 1 d . U . . .
N2 N 0.46055(18) 0.5214(3) 0.58835(10) 0.0184(6) Uani 1 1 d . U . . .
C1 C 0.0953(2) 0.3456(3) 0.72882(12) 0.0145(6) Uani 1 1 d . U . . .
C2 C 0.0609(2) 0.3697(3) 0.67917(13) 0.0179(7) Uani 1 1 d . U . . .
H2 H 0.089332 0.428967 0.654806 0.022 Uiso 1 1 calc R . . . .
C3 C -0.0168(2) 0.3032(4) 0.66684(13) 0.0200(7) Uani 1 1 d . U . . .
H3 H -0.042835 0.319570 0.633621 0.024 Uiso 1 1 calc R . . . .
C4 C -0.0581(2) 0.2125(4) 0.70200(14) 0.0217(7) Uani 1 1 d . U . . .
H4 H -0.111160 0.168390 0.692198 0.026 Uiso 1 1 calc R . . . .
C5 C -0.0224(2) 0.1867(3) 0.75067(14) 0.0189(7) Uani 1 1 d . U . . .
H5 H -0.050131 0.124779 0.774386 0.023 Uiso 1 1 calc R . . . .
C6 C 0.0556(2) 0.2537(3) 0.76448(12) 0.0144(6) Uani 1 1 d . U . . .
C7 C 0.1090(2) 0.2536(3) 0.81118(12) 0.0150(6) Uani 1 1 d . U . . .
C8 C 0.1046(2) 0.1840(4) 0.85928(13) 0.0199(7) Uani 1 1 d . U . . .
H8 H 0.059288 0.119196 0.866064 0.024 Uiso 1 1 calc R . . . .
C9 C 0.1677(2) 0.2114(4) 0.89674(13) 0.0240(7) Uani 1 1 d . U . . .
H9 H 0.165849 0.164332 0.929423 0.029 Uiso 1 1 calc R . . . .
C10 C 0.2339(2) 0.3075(4) 0.88704(14) 0.0243(8) Uani 1 1 d . U . . .
H10 H 0.275844 0.325621 0.913612 0.029 Uiso 1 1 calc R . . . .
C11 C 0.2402(2) 0.3771(4) 0.83975(13) 0.0205(7) Uani 1 1 d . U . . .
H11 H 0.285551 0.442246 0.833481 0.025 Uiso 1 1 calc R . . . .
C12 C 0.1776(2) 0.3480(3) 0.80164(12) 0.0158(6) Uani 1 1 d . U . . .
C13 C 0.2307(2) 0.4934(3) 0.72537(13) 0.0179(7) Uani 1 1 d . U . . .
H13A H 0.263317 0.547822 0.751791 0.022 Uiso 1 1 calc R . . . .
H13B H 0.198599 0.559378 0.702724 0.022 Uiso 1 1 calc R . . . .
C14 C 0.2949(2) 0.4114(3) 0.69211(13) 0.0178(7) Uani 1 1 d . U . . .
H14A H 0.262345 0.352162 0.667144 0.021 Uiso 1 1 calc R . . . .
H14B H 0.330100 0.350117 0.714980 0.021 Uiso 1 1 calc R . . . .
C15 C 0.3552(2) 0.5081(4) 0.66195(13) 0.0200(7) Uani 1 1 d . U . . .
H15A H 0.320005 0.579364 0.643620 0.024 Uiso 1 1 calc R . . . .
H15B H 0.394673 0.556119 0.686734 0.024 Uiso 1 1 calc R . . . .
C16 C 0.4083(2) 0.4283(4) 0.62267(14) 0.0220(7) Uani 1 1 d . U . . .
H16A H 0.448089 0.364427 0.641440 0.026 Uiso 1 1 calc R . . . .
H16B H 0.368742 0.371610 0.600700 0.026 Uiso 1 1 calc R . . . .
C17 C 0.5487(2) 0.5154(4) 0.58915(13) 0.0193(7) Uani 1 1 d . U . . .
H17 H 0.577537 0.453782 0.612513 0.023 Uiso 1 1 calc R . . . .
C18 C 0.5967(2) 0.5984(4) 0.55613(14) 0.0235(7) Uani 1 1 d . U . . .
H18 H 0.658576 0.592681 0.556077 0.028 Uiso 1 1 calc R . . . .
C19 C 0.5550(3) 0.6896(4) 0.52324(14) 0.0286(8) Uani 1 1 d . U . . .
H19 H 0.587622 0.747894 0.500492 0.034 Uiso 1 1 calc R . . . .
C20 C 0.4641(3) 0.6953(5) 0.52374(14) 0.0338(9) Uani 1 1 d . U . . .
H20 H 0.434200 0.758791 0.501634 0.041 Uiso 1 1 calc R . . . .
C21 C 0.4181(2) 0.6090(5) 0.55623(14) 0.0284(8) Uani 1 1 d . U . . .
H21 H 0.356054 0.610997 0.556070 0.034 Uiso 1 1 calc R . . . .
Cl1B Cl 0.8720(8) 0.4141(3) 0.42491(13) 0.034(2) Uani 0.343(13) 1 d . U P A 2
Cl1A Cl 0.8242(3) 0.4102(2) 0.42368(9) 0.0380(7) Uani 0.657(13) 1 d . U P A 1
O1A O 0.7598(2) 0.6651(5) 0.48227(12) 0.0359(10) Uani 0.779(5) 1 d . U P B 1
H1AA H 0.748453 0.745652 0.468483 0.054 Uiso 0.779(5) 1 d G . P B 1
H1AB H 0.743795 0.599905 0.460699 0.054 Uiso 0.779(5) 1 d G . P B 1
O1B O 1.0308(8) 0.4948(17) 0.4588(4) 0.0359(10) Uani 0.221(5) 1 d . U P B 2
H1BA H 0.974228 0.494075 0.456031 0.054 Uiso 0.78(6) 1 d G . P C 2
H1BB H 1.045347 0.512533 0.491065 0.054 Uiso 0.78(6) 1 d G . P C 2


_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 C1 1.383(4) . ?
N1 C12 1.383(4) . ?
N1 C13 1.456(4) . ?
N2 C16 1.487(4) . ?
N2 C17 1.352(4) . ?
N2 C21 1.345(5) . ?
C1 C2 1.392(5) . ?
C1 C6 1.407(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.388(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.404(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.380(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.404(5) . ?
C6 C7 1.446(5) . ?
C7 C8 1.400(5) . ?
C7 C12 1.410(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.384(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.396(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.384(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.395(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.520(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.521(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.503(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17 0.9500 . ?
C17 C18 1.375(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.373(6) . ?
C19 H19 0.9500 . ?
C19 C20 1.393(6) . ?
C20 H20 0.9500 . ?
C20 C21 1.370(6) . ?
C21 H21 0.9500 . ?
O1A H1AA 0.8701 . ?
O1A H1AB 0.8702 . ?
O1B H1BA 0.8690 . ?
O1B H1BB 0.8701 . ?

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
C1 N1 C12 108.5(3) . . ?
C1 N1 C13 124.9(3) . . ?
C12 N1 C13 126.2(3) . . ?
C17 N2 C16 120.2(3) . . ?
C21 N2 C16 118.5(3) . . ?
C21 N2 C17 121.3(3) . . ?
N1 C1 C2 128.9(3) . . ?
N1 C1 C6 109.1(3) . . ?
C2 C1 C6 122.0(3) . . ?
C1 C2 H2 121.5 . . ?
C3 C2 C1 117.0(3) . . ?
C3 C2 H2 121.5 . . ?
C2 C3 H3 119.0 . . ?
C2 C3 C4 122.0(3) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.6(3) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.6 . . ?
C4 C5 C6 118.7(3) . . ?
C6 C5 H5 120.6 . . ?
C1 C6 C7 106.8(3) . . ?
C5 C6 C1 119.6(3) . . ?
C5 C6 C7 133.5(3) . . ?
C8 C7 C6 134.1(3) . . ?
C8 C7 C12 119.8(3) . . ?
C12 C7 C6 106.2(3) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 C7 118.7(3) . . ?
C9 C8 H8 120.6 . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.7(3) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 119.1 . . ?
C11 C10 C9 121.8(3) . . ?
C11 C10 H10 119.1 . . ?
C10 C11 H11 121.2 . . ?
C10 C11 C12 117.6(3) . . ?
C12 C11 H11 121.2 . . ?
N1 C12 C7 109.4(3) . . ?
N1 C12 C11 129.2(3) . . ?
C11 C12 C7 121.4(3) . . ?
N1 C13 H13A 109.2 . . ?
N1 C13 H13B 109.2 . . ?
N1 C13 C14 112.0(3) . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 C15 110.9(3) . . ?
H14A C14 H14B 108.1 . . ?
C15 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C16 C15 C14 110.6(3) . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
N2 C16 C15 112.1(3) . . ?
N2 C16 H16A 109.2 . . ?
N2 C16 H16B 109.2 . . ?
C15 C16 H16A 109.2 . . ?
C15 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
N2 C17 H17 120.0 . . ?
N2 C17 C18 120.0(3) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.0(3) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 120.5 . . ?
C18 C19 C20 119.0(4) . . ?
C20 C19 H19 120.5 . . ?
C19 C20 H20 120.1 . . ?
C21 C20 C19 119.7(4) . . ?
C21 C20 H20 120.1 . . ?
N2 C21 C20 120.1(3) . . ?
N2 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
H1AA O1A H1AB 109.4 . . ?
H1BA O1B H1BB 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_PLAT094_mw368_0m_a          
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       4.77 Report
RESPONSE: Residual density around disordered atoms.
;
####################################################################### 
# 
# 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_mw334
_database_code_depnum_ccdc_archive 'CCDC 2024263'
loop_
_audit_author_name
_audit_author_address
'Duane Hean'
;University of British Columbia
Canada
;
_audit_update_record             
;
2020-08-19 deposited with the CCDC.	2021-07-28 downloaded from the CCDC.
;
_audit_creation_date             2019-10-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H21 N2, 0.91(Br), Br0.09 H2 O'
_chemical_formula_sum            'C21 H23 Br N2 O'
_chemical_formula_weight         399.32
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   15.2783(11)
_cell_length_b                   9.6864(7)
_cell_length_c                   25.9263(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3836.9(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9942
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      28.230
_cell_measurement_theta_min      2.611
_shelx_estimated_absorpt_T_max   0.948
_shelx_estimated_absorpt_T_min   0.537
_exptl_absorpt_coefficient_mu    2.153
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6347
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0626 before and 0.0366 after correction. The Ratio of minimum to maximum transmission is 0.8511. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.025
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            27795
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_min         2.060
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3773
_reflns_number_total             4743
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         1.518
_refine_diff_density_min         -0.985
_refine_diff_density_rms         0.093
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         4743
_refine_ls_number_restraints     345
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0520
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0588P)²+10.8450P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1288
_refine_ls_wR_factor_ref         0.1391
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
Uanis(Br1B) = Uanis(Br1A)
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(Br1B)=1-FVAR(1)
 Sof(Br1A)=FVAR(1)
5.a Free rotating group:
 O1(H1B,H1)
5.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C17(H17),
 C18(H18), C19(H19), C20(H20), C21(H21)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
N1 N 0.83087(15) 0.6094(2) 0.24486(10) 0.0192(5) Uani 1 1 d . U . . .
N2 N 0.54681(16) 0.4763(3) 0.41081(9) 0.0223(5) Uani 1 1 d . U . . .
C1 C 0.82327(18) 0.6628(3) 0.19551(12) 0.0198(6) Uani 1 1 d . U . . .
C2 C 0.76102(19) 0.6347(4) 0.15711(13) 0.0272(7) Uani 1 1 d . U . . .
H2 H 0.714863 0.570809 0.162841 0.033 Uiso 1 1 calc R . . . .
C3 C 0.7693(2) 0.7036(4) 0.11055(13) 0.0298(7) Uani 1 1 d . U . . .
H3 H 0.728079 0.686007 0.083933 0.036 Uiso 1 1 calc R . . . .
C4 C 0.8373(2) 0.7989(4) 0.10154(13) 0.0299(7) Uani 1 1 d . U . . .
H4 H 0.840378 0.845686 0.069382 0.036 Uiso 1 1 calc R . . . .
C5 C 0.8995(2) 0.8252(3) 0.13904(12) 0.0246(6) Uani 1 1 d . U . . .
H5 H 0.945584 0.888852 0.132766 0.030 Uiso 1 1 calc R . . . .
C6 C 0.89333(17) 0.7562(3) 0.18651(12) 0.0195(5) Uani 1 1 d . U . . .
C7 C 0.94587(17) 0.7560(3) 0.23288(11) 0.0177(5) Uani 1 1 d . U . . .
C8 C 1.02415(18) 0.8213(3) 0.24715(12) 0.0203(6) Uani 1 1 d . U . . .
H8 H 1.052936 0.881734 0.223794 0.024 Uiso 1 1 calc R . . . .
C9 C 1.05902(18) 0.7970(3) 0.29545(12) 0.0224(6) Uani 1 1 d . U . . .
H9 H 1.111950 0.841067 0.305423 0.027 Uiso 1 1 calc R . . . .
C10 C 1.01650(18) 0.7075(3) 0.32983(12) 0.0217(6) Uani 1 1 d . U . . .
H10 H 1.041901 0.691370 0.362725 0.026 Uiso 1 1 calc R . . . .
C11 C 0.93851(18) 0.6418(3) 0.31739(11) 0.0195(6) Uani 1 1 d . U . . .
H11 H 0.909502 0.583224 0.341305 0.023 Uiso 1 1 calc R . . . .
C12 C 0.90462(17) 0.6656(3) 0.26810(12) 0.0175(5) Uani 1 1 d . U . . .
C13 C 0.76805(18) 0.5192(3) 0.27027(12) 0.0220(6) Uani 1 1 d . U . . .
H13A H 0.800143 0.448682 0.290452 0.026 Uiso 1 1 calc R . . . .
H13B H 0.733108 0.470528 0.243742 0.026 Uiso 1 1 calc R . . . .
C14 C 0.70657(18) 0.5972(3) 0.30601(12) 0.0200(6) Uani 1 1 d . U . . .
H14A H 0.671863 0.664248 0.285699 0.024 Uiso 1 1 calc R . . . .
H14B H 0.741274 0.649413 0.331692 0.024 Uiso 1 1 calc R . . . .
C15 C 0.64464(18) 0.4980(3) 0.33400(12) 0.0203(6) Uani 1 1 d . U . . .
H15A H 0.600474 0.462187 0.309470 0.024 Uiso 1 1 calc R . . . .
H15B H 0.678245 0.418661 0.347690 0.024 Uiso 1 1 calc R . . . .
C16 C 0.5993(2) 0.5720(3) 0.37780(13) 0.0278(7) Uani 1 1 d . U . . .
H16A H 0.643793 0.618677 0.399407 0.033 Uiso 1 1 calc R . . . .
H16B H 0.560197 0.643841 0.363425 0.033 Uiso 1 1 calc R . . . .
C17 C 0.5888(2) 0.3793(4) 0.43841(12) 0.0324(8) Uani 1 1 d . U . . .
H17 H 0.650687 0.371627 0.436235 0.039 Uiso 1 1 calc R . . . .
C18 C 0.5424(2) 0.2907(5) 0.46984(13) 0.0403(9) Uani 1 1 d . U . . .
H18 H 0.572018 0.220846 0.488730 0.048 Uiso 1 1 calc R . . . .
C19 C 0.4521(2) 0.3045(4) 0.47372(13) 0.0321(7) Uani 1 1 d . U . . .
H19 H 0.419397 0.245322 0.495694 0.039 Uiso 1 1 calc R . . . .
C20 C 0.4102(2) 0.4062(3) 0.44494(12) 0.0272(7) Uani 1 1 d . U . . .
H20 H 0.348623 0.417676 0.447290 0.033 Uiso 1 1 calc R . . . .
C21 C 0.45901(19) 0.4904(3) 0.41291(12) 0.0246(6) Uani 1 1 d . U . . .
H21 H 0.430716 0.558257 0.392366 0.029 Uiso 1 1 calc R . . . .
Br1A Br 0.84174(2) 1.08200(4) -0.07984(2) 0.02945(13) Uani 0.9135(9) 1 d . U P
A 1
Br1B Br 0.8178(3) 1.0442(4) -0.05242(18) 0.02945(13) Uani 0.0865(9) 1 d . U P A
2
O1 O 0.75334(18) 0.8321(3) -0.01246(10) 0.0424(7) Uani 1 1 d . U . . .
H1B H 0.780380 0.893130 -0.031296 0.064 Uiso 1 1 d G . . . .
H1 H 0.723149 0.777451 -0.032295 0.064 Uiso 1 1 d G . . . .


_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 C1 1.385(4) . ?
N1 C12 1.389(3) . ?
N1 C13 1.456(4) . ?
N2 C16 1.495(4) . ?
N2 C17 1.344(4) . ?
N2 C21 1.349(4) . ?
C1 C2 1.404(4) . ?
C1 C6 1.421(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.385(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.409(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.404(4) . ?
C6 C7 1.445(4) . ?
C7 C8 1.403(4) . ?
C7 C12 1.413(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.381(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.403(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.389(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.398(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.521(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.531(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.511(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17 0.9500 . ?
C17 C18 1.379(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.391(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.391(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.382(4) . ?
C21 H21 0.9500 . ?
Br1B H1B 1.6637 . ?
O1 H1B 0.8710 . ?
O1 H1 0.8704 . ?

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
C1 N1 C12 108.8(2) . . ?
C1 N1 C13 126.0(2) . . ?
C12 N1 C13 125.0(3) . . ?
C17 N2 C16 118.8(3) . . ?
C17 N2 C21 121.6(3) . . ?
C21 N2 C16 119.6(3) . . ?
N1 C1 C2 129.8(3) . . ?
N1 C1 C6 109.0(2) . . ?
C2 C1 C6 121.2(3) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 C1 117.6(3) . . ?
C3 C2 H2 121.2 . . ?
C2 C3 H3 119.1 . . ?
C2 C3 C4 121.9(3) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.7(3) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.6 . . ?
C4 C5 C6 118.9(3) . . ?
C6 C5 H5 120.6 . . ?
C1 C6 C7 106.3(3) . . ?
C5 C6 C1 119.8(3) . . ?
C5 C6 C7 133.8(3) . . ?
C8 C7 C6 133.8(3) . . ?
C8 C7 C12 119.3(3) . . ?
C12 C7 C6 106.9(2) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 C7 119.4(3) . . ?
C9 C8 H8 120.3 . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.2(3) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 118.9 . . ?
C11 C10 C9 122.2(3) . . ?
C11 C10 H10 118.9 . . ?
C10 C11 H11 121.5 . . ?
C10 C11 C12 117.0(3) . . ?
C12 C11 H11 121.5 . . ?
N1 C12 C7 108.9(3) . . ?
N1 C12 C11 129.2(3) . . ?
C11 C12 C7 121.9(3) . . ?
N1 C13 H13A 109.1 . . ?
N1 C13 H13B 109.1 . . ?
N1 C13 C14 112.6(2) . . ?
H13A C13 H13B 107.8 . . ?
C14 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
C13 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
C13 C14 C15 111.0(2) . . ?
H14A C14 H14B 108.0 . . ?
C15 C14 H14A 109.4 . . ?
C15 C14 H14B 109.4 . . ?
C14 C15 H15A 109.7 . . ?
C14 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
C16 C15 C14 110.0(2) . . ?
C16 C15 H15A 109.7 . . ?
C16 C15 H15B 109.7 . . ?
N2 C16 C15 112.5(2) . . ?
N2 C16 H16A 109.1 . . ?
N2 C16 H16B 109.1 . . ?
C15 C16 H16A 109.1 . . ?
C15 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
N2 C17 H17 119.9 . . ?
N2 C17 C18 120.3(3) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 120.2 . . ?
C17 C18 C19 119.6(3) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 120.5 . . ?
C18 C19 C20 119.0(3) . . ?
C20 C19 H19 120.5 . . ?
C19 C20 H20 120.2 . . ?
C21 C20 C19 119.5(3) . . ?
C21 C20 H20 120.2 . . ?
N2 C21 C20 120.0(3) . . ?
N2 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
H1B O1 H1 109.4 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mw360_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2024264'
loop_
_audit_author_name
_audit_author_address
'Duane Hean'
;University of British Columbia
Canada
;
_audit_update_record             
;
2020-08-19 deposited with the CCDC.	2021-07-28 downloaded from the CCDC.
;
_audit_creation_date             2019-10-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H21 N2, F6 P'
_chemical_formula_sum            'C21 H21 F6 N2 P'
_chemical_formula_weight         446.37
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   16.349(7)
_cell_length_b                   9.779(4)
_cell_length_c                   24.784(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3962(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9905
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      30.51
_cell_measurement_theta_min      2.48
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.913
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0573 before and 0.0507 after correction. The Ratio of minimum to maximum transmission is 0.9619. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.455
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            56137
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.642
_diffrn_reflns_theta_min         1.643
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4921
_reflns_number_total             6096
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         6096
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0362
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0377P)²+2.0894P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0902
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C17(H17),
 C18(H18), C19(H19), C20(H20), C21(H21)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
N1 N 0.81522(6) 0.61552(10) 0.22177(4) 0.01299(19) Uani 1 1 d . . . . .
N2 N 0.56585(6) 0.49333(10) 0.40558(4) 0.01370(19) Uani 1 1 d . . . . .
C1 C 0.88428(7) 0.68207(11) 0.24025(4) 0.0115(2) Uani 1 1 d . . . . .
C2 C 0.92391(7) 0.66765(12) 0.28966(4) 0.0137(2) Uani 1 1 d . . . . .
H2 H 0.903161 0.608732 0.316896 0.016 Uiso 1 1 calc R . . . .
C3 C 0.99464(8) 0.74249(12) 0.29750(5) 0.0162(2) Uani 1 1 d . . . . .
H3 H 1.023544 0.733594 0.330572 0.019 Uiso 1 1 calc R . . . .
C4 C 1.02463(8) 0.83108(13) 0.25781(5) 0.0184(2) Uani 1 1 d . . . . .
H4 H 1.073079 0.881925 0.264534 0.022 Uiso 1 1 calc R . . . .
C5 C 0.98474(8) 0.84569(12) 0.20890(5) 0.0170(2) Uani 1 1 d . . . . .
H5 H 1.005414 0.905946 0.182103 0.020 Uiso 1 1 calc R . . . .
C6 C 0.91373(7) 0.77049(11) 0.19964(4) 0.0123(2) Uani 1 1 d . . . . .
C7 C 0.85875(7) 0.75615(11) 0.15419(4) 0.0130(2) Uani 1 1 d . . . . .
C8 C 0.85704(8) 0.81045(12) 0.10195(5) 0.0167(2) Uani 1 1 d . . . . .
H8 H 0.896979 0.875005 0.090701 0.020 Uiso 1 1 calc R . . . .
C9 C 0.79603(9) 0.76827(13) 0.06700(5) 0.0199(3) Uani 1 1 d . . . . .
H9 H 0.794248 0.804214 0.031406 0.024 Uiso 1 1 calc R . . . .
C10 C 0.73704(8) 0.67359(13) 0.08331(5) 0.0199(3) Uani 1 1 d . . . . .
H10 H 0.696174 0.645776 0.058367 0.024 Uiso 1 1 calc R . . . .
C11 C 0.73656(8) 0.61919(13) 0.13492(5) 0.0173(2) Uani 1 1 d . . . . .
H11 H 0.695579 0.556358 0.146036 0.021 Uiso 1 1 calc R . . . .
C12 C 0.79860(7) 0.66035(12) 0.16984(4) 0.0131(2) Uani 1 1 d . . . . .
C13 C 0.76540(7) 0.52315(12) 0.25364(4) 0.0139(2) Uani 1 1 d . . . . .
H13A H 0.801336 0.456316 0.272032 0.017 Uiso 1 1 calc R . . . .
H13B H 0.728387 0.471761 0.229385 0.017 Uiso 1 1 calc R . . . .
C14 C 0.71477(8) 0.59847(12) 0.29557(5) 0.0158(2) Uani 1 1 d . . . . .
H14A H 0.679512 0.666562 0.277332 0.019 Uiso 1 1 calc R . . . .
H14B H 0.751720 0.648224 0.320399 0.019 Uiso 1 1 calc R . . . .
C15 C 0.66160(8) 0.50055(12) 0.32788(5) 0.0152(2) Uani 1 1 d . . . . .
H15A H 0.616254 0.466253 0.305127 0.018 Uiso 1 1 calc R . . . .
H15B H 0.694526 0.421331 0.339992 0.018 Uiso 1 1 calc R . . . .
C16 C 0.62758(8) 0.57613(13) 0.37628(5) 0.0191(2) Uani 1 1 d . . . . .
H16A H 0.672896 0.599371 0.401139 0.023 Uiso 1 1 calc R . . . .
H16B H 0.602136 0.662661 0.364106 0.023 Uiso 1 1 calc R . . . .
C17 C 0.59017(8) 0.39537(13) 0.44006(5) 0.0169(2) Uani 1 1 d . . . . .
H17 H 0.646842 0.379551 0.445794 0.020 Uiso 1 1 calc R . . . .
C18 C 0.53305(9) 0.31795(13) 0.46708(5) 0.0186(2) Uani 1 1 d . . . . .
H18 H 0.549997 0.248936 0.491633 0.022 Uiso 1 1 calc R . . . .
C19 C 0.45079(8) 0.34150(13) 0.45818(5) 0.0181(2) Uani 1 1 d . . . . .
H19 H 0.410786 0.289028 0.476729 0.022 Uiso 1 1 calc R . . . .
C20 C 0.42706(8) 0.44177(14) 0.42216(5) 0.0203(3) Uani 1 1 d . . . . .
H20 H 0.370754 0.458866 0.415521 0.024 Uiso 1 1 calc R . . . .
C21 C 0.48643(8) 0.51640(13) 0.39607(5) 0.0180(2) Uani 1 1 d . . . . .
H21 H 0.470878 0.585139 0.370998 0.022 Uiso 1 1 calc R . . . .
P1 P 0.62371(2) 0.95442(3) 0.43210(2) 0.01344(7) Uani 1 1 d . . . . .
F1 F 0.54889(5) 1.04269(8) 0.40987(3) 0.02283(17) Uani 1 1 d . . . . .
F2 F 0.64784(5) 0.91323(7) 0.37127(3) 0.01785(15) Uani 1 1 d . . . . .
F3 F 0.69836(5) 0.86342(10) 0.45356(3) 0.0294(2) Uani 1 1 d . . . . .
F4 F 0.60046(5) 0.99373(8) 0.49268(3) 0.02252(17) Uani 1 1 d . . . . .
F5 F 0.56484(5) 0.82367(8) 0.43537(3) 0.02285(17) Uani 1 1 d . . . . .
F6 F 0.68191(6) 1.08513(9) 0.42827(4) 0.0317(2) Uani 1 1 d . . . . .


_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 C1 1.3814(15) . ?
N1 C12 1.3863(15) . ?
N1 C13 1.4504(15) . ?
N2 C16 1.4836(16) . ?
N2 C17 1.3441(16) . ?
N2 C21 1.3388(17) . ?
C1 C2 1.3927(16) . ?
C1 C6 1.4115(15) . ?
C2 H2 0.9500 . ?
C2 C3 1.3823(17) . ?
C3 H3 0.9500 . ?
C3 C4 1.3996(18) . ?
C4 H4 0.9500 . ?
C4 C5 1.3838(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.3933(17) . ?
C6 C7 1.4480(17) . ?
C7 C8 1.3996(16) . ?
C7 C12 1.4126(17) . ?
C8 H8 0.9500 . ?
C8 C9 1.3840(19) . ?
C9 H9 0.9500 . ?
C9 C10 1.397(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.3851(17) . ?
C11 H11 0.9500 . ?
C11 C12 1.3929(17) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.5191(16) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.5211(16) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.5148(17) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17 0.9500 . ?
C17 C18 1.3762(18) . ?
C18 H18 0.9500 . ?
C18 C19 1.382(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.3817(18) . ?
C20 H20 0.9500 . ?
C20 C21 1.3758(18) . ?
C21 H21 0.9500 . ?
P1 F1 1.5951(9) . ?
P1 F2 1.6094(9) . ?
P1 F3 1.6015(10) . ?
P1 F4 1.5958(9) . ?
P1 F5 1.6025(10) . ?
P1 F6 1.5964(10) . ?

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
C1 N1 C12 108.60(9) . . ?
C1 N1 C13 124.88(10) . . ?
C12 N1 C13 126.34(10) . . ?
C17 N2 C16 119.93(11) . . ?
C21 N2 C16 118.79(11) . . ?
C21 N2 C17 121.26(11) . . ?
N1 C1 C2 128.62(10) . . ?
N1 C1 C6 109.33(10) . . ?
C2 C1 C6 122.03(11) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 C1 117.33(11) . . ?
C3 C2 H2 121.3 . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.47(11) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 120.97(12) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 120.6 . . ?
C4 C5 C6 118.85(11) . . ?
C6 C5 H5 120.6 . . ?
C1 C6 C7 106.47(10) . . ?
C5 C6 C1 119.35(11) . . ?
C5 C6 C7 134.15(11) . . ?
C8 C7 C6 134.05(12) . . ?
C8 C7 C12 119.46(11) . . ?
C12 C7 C6 106.42(10) . . ?
C7 C8 H8 120.7 . . ?
C9 C8 C7 118.70(12) . . ?
C9 C8 H8 120.7 . . ?
C8 C9 H9 119.5 . . ?
C8 C9 C10 120.94(11) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 119.1 . . ?
C11 C10 C9 121.72(12) . . ?
C11 C10 H10 119.1 . . ?
C10 C11 H11 121.3 . . ?
C10 C11 C12 117.31(12) . . ?
C12 C11 H11 121.3 . . ?
N1 C12 C7 109.17(10) . . ?
N1 C12 C11 128.91(11) . . ?
C11 C12 C7 121.86(11) . . ?
N1 C13 H13A 109.2 . . ?
N1 C13 H13B 109.2 . . ?
N1 C13 C14 112.12(10) . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
C13 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
C13 C14 C15 111.48(10) . . ?
H14A C14 H14B 108.0 . . ?
C15 C14 H14A 109.3 . . ?
C15 C14 H14B 109.3 . . ?
C14 C15 H15A 110.0 . . ?
C14 C15 H15B 110.0 . . ?
H15A C15 H15B 108.3 . . ?
C16 C15 C14 108.63(10) . . ?
C16 C15 H15A 110.0 . . ?
C16 C15 H15B 110.0 . . ?
N2 C16 C15 111.77(10) . . ?
N2 C16 H16A 109.3 . . ?
N2 C16 H16B 109.3 . . ?
C15 C16 H16A 109.3 . . ?
C15 C16 H16B 109.3 . . ?
H16A C16 H16B 107.9 . . ?
N2 C17 H17 120.0 . . ?
N2 C17 C18 120.05(12) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 120.3 . . ?
C17 C18 C19 119.41(12) . . ?
C19 C18 H18 120.3 . . ?
C18 C19 H19 120.2 . . ?
C20 C19 C18 119.65(12) . . ?
C20 C19 H19 120.2 . . ?
C19 C20 H20 120.6 . . ?
C21 C20 C19 118.82(12) . . ?
C21 C20 H20 120.6 . . ?
N2 C21 C20 120.80(11) . . ?
N2 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
F1 P1 F2 90.00(4) . . ?
F1 P1 F3 178.84(5) . . ?
F1 P1 F4 90.68(5) . . ?
F1 P1 F5 89.35(6) . . ?
F1 P1 F6 90.19(6) . . ?
F3 P1 F2 89.15(5) . . ?
F3 P1 F5 89.86(6) . . ?
F4 P1 F2 179.28(5) . . ?
F4 P1 F3 90.17(5) . . ?
F4 P1 F5 90.09(4) . . ?
F4 P1 F6 90.28(5) . . ?
F5 P1 F2 89.71(4) . . ?
F6 P1 F2 89.92(5) . . ?
F6 P1 F3 90.59(6) . . ?
F6 P1 F5 179.41(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mw381_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2024265'
loop_
_audit_author_name
_audit_author_address
'Duane Hean'
;University of British Columbia
Canada
;
_audit_update_record             
;
2020-08-19 deposited with the CCDC.	2021-07-28 downloaded from the CCDC.
;
# end Validation Reply Form
_audit_creation_date             2020-01-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'C21 H21 N2, B0.38 Br0.2 F1.51 H1.25 O0.28, 0.4(Br)'
_chemical_formula_sum            'C21 H22.24 B0.38 Br0.61 F1.51 N2 O0.28'
_chemical_formula_weight         388.21
_chemical_melting_point          ?
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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   15.183(8)
_cell_length_b                   9.740(5)
_cell_length_c                   25.145(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3719(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4256
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      26.838
_cell_measurement_theta_min      2.615
_shelx_estimated_absorpt_T_max   0.886
_shelx_estimated_absorpt_T_min   0.639
_exptl_absorpt_coefficient_mu    1.384
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1184 before and 0.0408 after correction. The Ratio of minimum to maximum transmission is 0.9323. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1609
_exptl_crystal_size_max          0.356
_exptl_crystal_size_mid          0.201
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            24415
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.661
_diffrn_reflns_theta_min         2.103
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3704
_reflns_number_total             5700
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         1.235
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         5700
_refine_ls_number_restraints     214
_refine_ls_R_factor_all          0.1082
_refine_ls_R_factor_gt           0.0678
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0757P)²+3.9138P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1749
_refine_ls_wR_factor_ref         0.1947
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 1*[Sof(Br1C)]+1*[Sof(Br1A)]+1*[Sof(B1)+Sof(F1)+Sof(F2)+Sof(F3)+Sof(F4)+
 Sof(H1B)+Sof(H1A)]+1*[Sof(Br1B)]=1 with esd of 0.01
 Sof(H1B)=Sof(H1A)=1-FVAR(3)
 Sof(B1)=Sof(F1)=Sof(F2)=Sof(F3)=Sof(F4)=FVAR(3)
4.a Free rotating group:
 B1(F1,F2,F3,F4), O1(H1B,H1A)
4.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C17(H17),
 C18(H18), C19(H19), C20(H20), C21(H21)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
N1 N 0.82839(13) 0.3749(2) 0.75817(10) 0.0344(5) Uani 1 1 d . U . . .
N2 N 0.54806(14) 0.5185(2) 0.58566(9) 0.0329(5) Uani 1 1 d . U . . .
C1 C 0.82143(16) 0.3221(3) 0.80886(12) 0.0354(6) Uani 1 1 d . U . . .
C2 C 0.75963(17) 0.3519(3) 0.84870(13) 0.0452(7) Uani 1 1 d . U . . .
H2 H 0.713245 0.415544 0.842800 0.054 Uiso 1 1 calc R . . . .
C3 C 0.7688(2) 0.2851(3) 0.89680(14) 0.0507(8) Uani 1 1 d . U . . .
H3 H 0.728025 0.304305 0.924484 0.061 Uiso 1 1 calc R . . . .
C4 C 0.8363(2) 0.1900(3) 0.90614(14) 0.0496(8) Uani 1 1 d . U . . .
H4 H 0.839530 0.144303 0.939453 0.060 Uiso 1 1 calc R . . . .
C5 C 0.89830(19) 0.1622(3) 0.86716(12) 0.0410(6) Uani 1 1 d . U . . .
H5 H 0.944327 0.098187 0.873552 0.049 Uiso 1 1 calc R . . . .
C6 C 0.89197(16) 0.2298(2) 0.81829(11) 0.0335(6) Uani 1 1 d . U . . .
C7 C 0.94472(15) 0.2302(2) 0.77056(11) 0.0308(5) Uani 1 1 d . U . . .
C8 C 1.02383(16) 0.1662(2) 0.75630(12) 0.0340(6) Uani 1 1 d . U . . .
H8 H 1.052485 0.105332 0.780229 0.041 Uiso 1 1 calc R . . . .
C9 C 1.05943(16) 0.1929(2) 0.70697(12) 0.0374(6) Uani 1 1 d . U . . .
H9 H 1.113448 0.150900 0.697028 0.045 Uiso 1 1 calc R . . . .
C10 C 1.01706(16) 0.2810(3) 0.67143(12) 0.0351(6) Uani 1 1 d . U . . .
H10 H 1.042990 0.297745 0.637667 0.042 Uiso 1 1 calc R . . . .
C11 C 0.93808(16) 0.3447(2) 0.68412(11) 0.0325(5) Uani 1 1 d . U . . .
H11 H 0.909046 0.403122 0.659474 0.039 Uiso 1 1 calc R . . . .
C12 C 0.90316(15) 0.3198(2) 0.73414(11) 0.0301(5) Uani 1 1 d . U . . .
C13 C 0.76608(16) 0.4648(3) 0.73151(12) 0.0360(6) Uani 1 1 d . U . . .
H13A H 0.798901 0.537671 0.712492 0.043 Uiso 1 1 calc R . . . .
H13B H 0.728317 0.509717 0.758491 0.043 Uiso 1 1 calc R . . . .
C14 C 0.70796(16) 0.3885(2) 0.69202(12) 0.0340(6) Uani 1 1 d . U . . .
H14A H 0.674336 0.316287 0.710901 0.041 Uiso 1 1 calc R . . . .
H14B H 0.745369 0.343263 0.664945 0.041 Uiso 1 1 calc R . . . .
C15 C 0.64393(17) 0.4868(3) 0.66460(11) 0.0347(6) Uani 1 1 d . U . . .
H15A H 0.595749 0.510945 0.689428 0.042 Uiso 1 1 calc R . . . .
H15B H 0.675193 0.572376 0.654854 0.042 Uiso 1 1 calc R . . . .
C16 C 0.60601(18) 0.4222(3) 0.61560(13) 0.0417(7) Uani 1 1 d . U . . .
H16A H 0.654646 0.391737 0.592176 0.050 Uiso 1 1 calc R . . . .
H16B H 0.571566 0.340024 0.625853 0.050 Uiso 1 1 calc R . . . .
C17 C 0.5839(2) 0.6280(3) 0.56103(12) 0.0453(7) Uani 1 1 d . U . . .
H17 H 0.645502 0.644036 0.563595 0.054 Uiso 1 1 calc R . . . .
C18 C 0.5318(2) 0.7170(4) 0.53210(12) 0.0531(8) Uani 1 1 d . U . . .
H18 H 0.556915 0.795084 0.515305 0.064 Uiso 1 1 calc R . . . .
C19 C 0.4432(2) 0.6910(3) 0.52797(12) 0.0458(7) Uani 1 1 d . U . . .
H19 H 0.406806 0.749641 0.507309 0.055 Uiso 1 1 calc R . . . .
C20 C 0.40703(19) 0.5790(3) 0.55397(12) 0.0405(6) Uani 1 1 d . U . . .
H20 H 0.345737 0.560395 0.551540 0.049 Uiso 1 1 calc R . . . .
C21 C 0.46110(17) 0.4955(3) 0.58326(12) 0.0371(6) Uani 1 1 d . U . . .
H21 H 0.436580 0.420154 0.602144 0.044 Uiso 1 1 calc R . . . .
B1 B 0.83693(18) 0.5453(3) 0.56203(13) 0.029(3) Uani 0.377(4) 1 d . U P A 3
F1 F 0.7865(2) 0.6220(5) 0.52592(19) 0.077(2) Uani 0.377(4) 1 d G U P A 3
F2 F 0.8102(3) 0.4076(3) 0.5604(2) 0.0662(18) Uani 0.377(4) 1 d G U P A 3
F3 F 0.92620(17) 0.5545(4) 0.54815(19) 0.0515(15) Uani 0.377(4) 1 d G U P A 3
F4 F 0.8248(4) 0.5974(5) 0.61348(14) 0.080(3) Uani 0.377(4) 1 d G U P A 3
Br1A Br 0.8415(7) 0.5678(8) 0.5770(6) 0.042(3) Uani 0.244(17) 1 d . U P B 1
Br1B Br 0.8202(5) 0.5401(8) 0.5509(6) 0.060(3) Uani 0.201(9) 1 d . U P C 4
Br1C Br 0.8531(8) 0.5757(9) 0.5850(5) 0.047(2) Uani 0.159(16) 1 d . U P D 2
O1 O 0.7468(5) 0.8242(9) 0.5159(3) 0.049(3) Uani 0.278(8) 1 d . U . . .
H1B H 0.739026 0.909105 0.522064 0.074 Uiso 0.623(4) 1 d G . P A 4
H1A H 0.794885 0.798128 0.529958 0.074 Uiso 0.623(4) 1 d G . P A 4


_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 C1 1.379(4) . ?
N1 C12 1.394(3) . ?
N1 C13 1.453(3) . ?
N2 C16 1.490(3) . ?
N2 C17 1.348(4) . ?
N2 C21 1.341(3) . ?
C1 C2 1.403(4) . ?
C1 C6 1.418(4) . ?
C2 C3 1.380(5) . ?
C3 C4 1.401(5) . ?
C4 C5 1.386(5) . ?
C5 C6 1.398(4) . ?
C6 C7 1.443(4) . ?
C7 C8 1.400(3) . ?
C7 C12 1.414(4) . ?
C8 C9 1.378(4) . ?
C9 C10 1.396(4) . ?
C10 C11 1.387(4) . ?
C11 C12 1.386(4) . ?
C13 C14 1.523(4) . ?
C14 C15 1.529(4) . ?
C15 C16 1.499(4) . ?
C17 C18 1.381(5) . ?
C18 C19 1.373(5) . ?
C19 C20 1.385(4) . ?
C20 C21 1.370(4) . ?
B1 F1 1.4029 . ?
B1 F2 1.4023 . ?
B1 F3 1.4024 . ?
B1 F4 1.4019 . ?
F2 O1 1.632(9) 8_755 ?

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
C1 N1 C12 108.6(2) . . ?
C1 N1 C13 127.0(2) . . ?
C12 N1 C13 124.2(2) . . ?
C17 N2 C16 119.4(2) . . ?
C21 N2 C16 119.9(2) . . ?
C21 N2 C17 120.6(2) . . ?
N1 C1 C2 129.4(3) . . ?
N1 C1 C6 109.5(2) . . ?
C2 C1 C6 121.1(3) . . ?
C3 C2 C1 117.4(3) . . ?
C2 C3 C4 122.1(3) . . ?
C5 C4 C3 120.5(3) . . ?
C4 C5 C6 118.9(3) . . ?
C1 C6 C7 106.2(2) . . ?
C5 C6 C1 119.8(3) . . ?
C5 C6 C7 134.0(3) . . ?
C8 C7 C6 133.5(2) . . ?
C8 C7 C12 119.5(3) . . ?
C12 C7 C6 107.0(2) . . ?
C9 C8 C7 118.9(2) . . ?
C8 C9 C10 120.8(2) . . ?
C11 C10 C9 121.7(3) . . ?
C12 C11 C10 117.5(2) . . ?
N1 C12 C7 108.7(2) . . ?
C11 C12 N1 129.6(2) . . ?
C11 C12 C7 121.7(2) . . ?
N1 C13 C14 112.6(2) . . ?
C13 C14 C15 110.9(2) . . ?
C16 C15 C14 110.6(2) . . ?
N2 C16 C15 112.2(2) . . ?
N2 C17 C18 120.5(3) . . ?
C19 C18 C17 119.1(3) . . ?
C18 C19 C20 119.9(3) . . ?
C21 C20 C19 118.9(3) . . ?
N2 C21 C20 121.0(3) . . ?
F2 B1 F1 109.4 . . ?
F2 B1 F3 109.5 . . ?
F3 B1 F1 109.4 . . ?
F4 B1 F1 109.4 . . ?
F4 B1 F2 109.6 . . ?
F4 B1 F3 109.5 . . ?
B1 F2 O1 130.5(4) . 8_755 ?

_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_PLAT094_mw381_0m_a          
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       4.77 Report
RESPONSE: Residual density around disordered atoms.
;
####################################################################### 
# 
# 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_mw481_a
_database_code_depnum_ccdc_archive 'CCDC 2052371'
loop_
_audit_author_name
_audit_author_address
'Duane Hean'
;University of British Columbia
Canada
;
_audit_update_record             
;
2020-12-24 deposited with the CCDC.	2021-07-28 downloaded from the CCDC.
;
_audit_creation_date             2020-12-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'Br, 0.5(C H2 Cl2.008), C21 H21 N2 O2 S, 0.5(H2 O)'
_chemical_formula_sum            'C21.50 H23 Br Cl N2 O2.50 S'
_chemical_formula_weight         497.01
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1050(6)
_cell_length_b                   12.2348(9)
_cell_length_c                   23.4041(16)
_cell_angle_alpha                95.281(2)
_cell_angle_beta                 95.216(2)
_cell_angle_gamma                106.432(2)
_cell_volume                     2199.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9822
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.58
_cell_measurement_theta_min      2.32
_shelx_estimated_absorpt_T_max   0.817
_shelx_estimated_absorpt_T_min   0.522
_exptl_absorpt_coefficient_mu    2.108
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5334
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0968 before and 0.0377 after correction.
The Ratio of minimum to maximum transmission is 0.7149.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.354
_exptl_crystal_size_mid          0.278
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            85969
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.661
_diffrn_reflns_theta_min         1.749
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                11478
_reflns_number_total             13535
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.369
_refine_diff_density_min         -0.693
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     573
_refine_ls_number_reflns         13535
_refine_ls_number_restraints     903
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0327
_refine_ls_restrained_S_all      0.978
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0378P)²+1.7496P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0773
_refine_ls_wR_factor_ref         0.0813
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(Cl1B)=Sof(Cl2B)=FVAR(1)
 Sof(Cl1A)=Sof(Cl2A)=FVAR(2)
 Sof(Cl1C)=Sof(Cl2C)=FVAR(3)
5.a Free rotating group:
 O1(H1A,H1B)
5.b Secondary CH2 refined with riding coordinates:
 C13A(H13A,H13B), C14A(H14A,H14B), C15A(H15A,H15B), C16A(H16A,H16B), C13B(H13C,
 H13D), C14B(H14C,H14D), C15B(H15C,H15D), C16B(H16C,H16D)
5.c Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C3A(H3A), C4A(H4A), C5A(H5A), C8A(H8A), C9A(H9A), C10A(H10A),
 C11A(H11A), C17A(H17A), C18A(H18A), C19A(H19A), C20A(H20A), C21A(H21A),
 C2B(H2B), C3B(H3B), C4B(H4B), C5B(H5B), C8B(H8B), C9B(H9B), C10B(H10B),
 C11B(H11B), C17B(H17B), C18B(H18B), C19B(H19B), C20B(H20B), C21B(H21B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Br1A Br 0.63541(2) 0.03679(2) 0.24182(2) 0.01880(4) Uani 1 1 d . . . . .
Br1B Br -0.27961(3) -0.37777(2) 0.27095(2) 0.03324(6) Uani 1 1 d . . . . .
Cl1A Cl 0.675(2) 0.3017(18) 0.1961(8) 0.028(2) Uani 0.16(2) 1 d . U P . .
Cl1B Cl 0.6590(5) 0.2875(4) 0.1868(3) 0.0173(9) Uani 0.67(2) 1 d . U P . .
Cl1C Cl 0.650(3) 0.2753(19) 0.1772(8) 0.0220(17) Uani 0.17(2) 1 d . U P . .
Cl2B Cl 0.4044(8) 0.3690(5) 0.1207(2) 0.0216(5) Uani 0.67(2) 1 d . U P . .
Cl2A Cl 0.419(2) 0.367(2) 0.1140(7) 0.0255(14) Uani 0.16(2) 1 d . U P . .
Cl2C Cl 0.417(2) 0.3868(11) 0.1253(7) 0.0218(11) Uani 0.17(2) 1 d . U P . .
C22 C 0.6313(2) 0.39776(15) 0.14621(8) 0.0211(3) Uani 1 1 d . U . . .
H22A H 0.667(3) 0.469(2) 0.1702(10) 0.027(6) Uiso 1 1 d . . . . .
H22B H 0.692(3) 0.400(2) 0.1157(11) 0.032(6) Uiso 1 1 d . . . . .
S1A S 0.11015(5) -0.26792(3) -0.02786(2) 0.01471(7) Uani 1 1 d . U . . .
O2A O 0.01369(17) -0.31628(11) -0.08398(5) 0.0227(3) Uani 1 1 d . U . . .
O3A O 0.24403(16) -0.31855(10) -0.00870(6) 0.0216(2) Uani 1 1 d . U . . .
N1A N 0.16651(18) -0.09622(11) 0.07828(6) 0.0153(2) Uani 1 1 d . U . . .
N2A N 0.13902(18) 0.29149(11) 0.27044(6) 0.0166(3) Uani 1 1 d . U . . .
C1A C 0.0241(2) -0.19376(13) 0.07491(7) 0.0142(3) Uani 1 1 d . U . . .
C2A C -0.0756(2) -0.21622(14) 0.12101(7) 0.0184(3) Uani 1 1 d . U . . .
H2A H -0.041269 -0.166882 0.156506 0.022 Uiso 1 1 calc R U . . .
C3A C -0.2229(2) -0.30911(15) 0.11534(8) 0.0219(3) Uani 1 1 d . U . . .
H3A H -0.287281 -0.322814 0.147245 0.026 Uiso 1 1 calc R U . . .
C4A C -0.2794(2) -0.38335(15) 0.06382(8) 0.0225(3) Uani 1 1 d . U . . .
H4A H -0.384378 -0.444287 0.059844 0.027 Uiso 1 1 calc R U . . .
C5A C -0.1798(2) -0.36649(14) 0.01879(7) 0.0188(3) Uani 1 1 d . U . . .
H5A H -0.213703 -0.417607 -0.016130 0.023 Uiso 1 1 calc R U . . .
C6A C -0.0288(2) -0.27402(13) 0.02473(7) 0.0147(3) Uani 1 1 d . U . . .
C7A C 0.19825(19) -0.12048(13) -0.02515(7) 0.0139(3) Uani 1 1 d . U . . .
C8A C 0.2524(2) -0.07583(14) -0.07551(7) 0.0168(3) Uani 1 1 d . U . . .
H8A H 0.230317 -0.124847 -0.111012 0.020 Uiso 1 1 calc R U . . .
C9A C 0.3379(2) 0.03959(15) -0.07351(8) 0.0194(3) Uani 1 1 d . U . . .
H9A H 0.373908 0.071000 -0.107546 0.023 Uiso 1 1 calc R U . . .
C10A C 0.3707(2) 0.10929(14) -0.02071(8) 0.0206(3) Uani 1 1 d . U . . .
H10A H 0.430630 0.188632 -0.018988 0.025 Uiso 1 1 calc R U . . .
C11A C 0.3177(2) 0.06548(14) 0.02924(7) 0.0183(3) Uani 1 1 d . U . . .
H11A H 0.342997 0.114974 0.064667 0.022 Uiso 1 1 calc R U . . .
C12A C 0.22675(19) -0.05156(13) 0.02835(7) 0.0141(3) Uani 1 1 d . U . . .
C13A C 0.2276(2) -0.02370(14) 0.13457(7) 0.0177(3) Uani 1 1 d . U . . .
H13A H 0.350680 0.020561 0.134989 0.021 Uiso 1 1 calc R U . . .
H13B H 0.221049 -0.073926 0.165645 0.021 Uiso 1 1 calc R U . . .
C14A C 0.1227(2) 0.06001(14) 0.14742(7) 0.0173(3) Uani 1 1 d . U . . .
H14A H 0.131619 0.111936 0.117066 0.021 Uiso 1 1 calc R U . . .
H14B H -0.000881 0.016257 0.146351 0.021 Uiso 1 1 calc R U . . .
C15A C 0.1865(2) 0.13135(13) 0.20633(7) 0.0154(3) Uani 1 1 d . U . . .
H15A H 0.167911 0.080906 0.237339 0.018 Uiso 1 1 calc R U . . .
H15B H 0.312041 0.171355 0.208899 0.018 Uiso 1 1 calc R U . . .
C16A C 0.0859(2) 0.21869(14) 0.21359(7) 0.0165(3) Uani 1 1 d . U . . .
H16A H 0.105292 0.268387 0.182282 0.020 Uiso 1 1 calc R U . . .
H16B H -0.039490 0.177714 0.209996 0.020 Uiso 1 1 calc R U . . .
C17A C 0.2883(2) 0.37819(14) 0.27870(8) 0.0197(3) Uani 1 1 d . U . . .
H17A H 0.358541 0.391718 0.248225 0.024 Uiso 1 1 calc R U . . .
C18A C 0.3398(3) 0.44720(16) 0.33078(8) 0.0266(4) Uani 1 1 d . U . . .
H18A H 0.444912 0.508256 0.336527 0.032 Uiso 1 1 calc R U . . .
C19A C 0.2360(3) 0.4262(2) 0.37460(9) 0.0419(6) Uani 1 1 d . U . . .
H19A H 0.268717 0.473202 0.410797 0.050 Uiso 1 1 calc R U . . .
C20A C 0.0839(3) 0.3361(2) 0.36546(9) 0.0458(7) Uani 1 1 d . U . . .
H20A H 0.012456 0.320715 0.395522 0.055 Uiso 1 1 calc R U . . .
C21A C 0.0367(3) 0.26895(17) 0.31276(8) 0.0292(4) Uani 1 1 d . U . . .
H21A H -0.067471 0.207082 0.306239 0.035 Uiso 1 1 calc R U . . .
S006 S 0.35936(6) 0.28379(4) 0.51974(2) 0.02778(10) Uani 1 1 d . U . . .
O1B O 0.4756(2) 0.35081(14) 0.56897(7) 0.0459(4) Uani 1 1 d . U . . .
O2B O 0.2086(2) 0.32061(12) 0.50356(7) 0.0349(3) Uani 1 1 d . U . . .
N1B N 0.28993(19) 0.08063(12) 0.42724(6) 0.0184(3) Uani 1 1 d . U . . .
N2B N 0.30650(18) -0.30541(12) 0.23548(6) 0.0189(3) Uani 1 1 d . U . . .
C1B C 0.2570(2) 0.05485(15) 0.48297(7) 0.0185(3) Uani 1 1 d . U . . .
C2B C 0.1872(2) -0.05922(16) 0.49393(8) 0.0249(4) Uani 1 1 d . U . . .
H2B H 0.158698 -0.119786 0.462928 0.030 Uiso 1 1 calc R U . . .
C3B C 0.1597(3) -0.08404(19) 0.54926(9) 0.0318(4) Uani 1 1 d . U . . .
H3B H 0.113617 -0.161793 0.555676 0.038 Uiso 1 1 calc R U . . .
C4B C 0.1979(2) 0.0023(2) 0.59605(8) 0.0307(4) Uani 1 1 d . U . . .
H4B H 0.178832 -0.016301 0.633907 0.037 Uiso 1 1 calc R U . . .
C5B C 0.2635(2) 0.11436(19) 0.58635(8) 0.0266(4) Uani 1 1 d . U . . .
H5B H 0.288913 0.174287 0.617569 0.032 Uiso 1 1 calc R U . . .
C6B C 0.2930(2) 0.14051(16) 0.53050(7) 0.0208(3) Uani 1 1 d . U . . .
C7B C 0.4691(3) 0.27798(16) 0.45971(9) 0.0286(4) Uani 1 1 d . U . . .
C8B C 0.6002(3) 0.37610(19) 0.45168(11) 0.0434(6) Uani 1 1 d . U . . .
H8B H 0.639111 0.438958 0.481513 0.052 Uiso 1 1 calc R U . . .
C9B C 0.6729(3) 0.3818(2) 0.40080(12) 0.0478(7) Uani 1 1 d . U . . .
H9B H 0.762466 0.447855 0.395218 0.057 Uiso 1 1 calc R U . . .
C10B C 0.6124(3) 0.28864(19) 0.35750(10) 0.0375(5) Uani 1 1 d . U . . .
H10B H 0.659044 0.293058 0.321692 0.045 Uiso 1 1 calc R U . . .
C11B C 0.4865(3) 0.19019(17) 0.36543(8) 0.0273(4) Uani 1 1 d . U . . .
H11B H 0.449638 0.127767 0.335323 0.033 Uiso 1 1 calc R U . . .
C12B C 0.4117(2) 0.18094(15) 0.41759(8) 0.0219(3) Uani 1 1 d . U . . .
C13B C 0.2176(2) -0.00988(15) 0.37815(7) 0.0195(3) Uani 1 1 d . U . . .
H13C H 0.197927 0.026741 0.343184 0.023 Uiso 1 1 calc R U . . .
H13D H 0.103595 -0.058184 0.386048 0.023 Uiso 1 1 calc R U . . .
C14B C 0.3317(2) -0.08732(14) 0.36543(7) 0.0192(3) Uani 1 1 d . U . . .
H14C H 0.452110 -0.039688 0.364119 0.023 Uiso 1 1 calc R U . . .
H14D H 0.332772 -0.136748 0.396576 0.023 Uiso 1 1 calc R U . . .
C15B C 0.2619(2) -0.16178(14) 0.30771(7) 0.0178(3) Uani 1 1 d . U . . .
H15C H 0.140441 -0.207684 0.308894 0.021 Uiso 1 1 calc R U . . .
H15D H 0.262833 -0.111984 0.276642 0.021 Uiso 1 1 calc R U . . .
C16B C 0.3700(2) -0.24173(15) 0.29427(7) 0.0209(3) Uani 1 1 d . U . . .
H16C H 0.493262 -0.196775 0.296030 0.025 Uiso 1 1 calc R U . . .
H16D H 0.360823 -0.296589 0.323231 0.025 Uiso 1 1 calc R U . . .
C17B C 0.3862(2) -0.26598(15) 0.19053(8) 0.0228(3) Uani 1 1 d . U . . .
H17B H 0.486753 -0.201397 0.196890 0.027 Uiso 1 1 calc R U . . .
C18B C 0.3227(3) -0.31887(17) 0.13501(8) 0.0263(4) Uani 1 1 d . U . . .
H18B H 0.378041 -0.290295 0.103069 0.032 Uiso 1 1 calc R U . . .
C19B C 0.1779(3) -0.41377(16) 0.12637(9) 0.0273(4) Uani 1 1 d . U . . .
H19B H 0.133039 -0.451209 0.088438 0.033 Uiso 1 1 calc R U . . .
C20B C 0.0986(3) -0.45393(16) 0.17356(9) 0.0300(4) Uani 1 1 d . U . . .
H20B H 0.000121 -0.519864 0.168341 0.036 Uiso 1 1 calc R U . . .
C21B C 0.1642(2) -0.39713(15) 0.22804(9) 0.0261(4) Uani 1 1 d . U . . .
H21B H 0.108854 -0.422705 0.260506 0.031 Uiso 1 1 calc R U . . .
O1 O -0.07408(18) -0.10161(12) 0.25559(7) 0.0291(3) Uani 1 1 d G . . . .
H1A H -0.119955 -0.170370 0.261779 0.044 Uiso 1 1 d G U . . .
H1B H -0.152227 -0.068270 0.250957 0.044 Uiso 1 1 d G 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 Cl1C 0.51(3) . ?
Cl1A C22 1.81(2) . ?
Cl1B C22 1.772(3) . ?
Cl1C C22 1.76(2) . ?
Cl2B C22 1.805(6) . ?
Cl2A C22 1.740(18) . ?
Cl2C C22 1.722(17) . ?
C22 H22A 0.95(2) . ?
C22 H22B 0.90(2) . ?
S1A O2A 1.4473(12) . ?
S1A O3A 1.4509(13) . ?
S1A C6A 1.7351(16) . ?
S1A C7A 1.7349(16) . ?
N1A C1A 1.396(2) . ?
N1A C12A 1.405(2) . ?
N1A C13A 1.4784(19) . ?
N2A C16A 1.4866(19) . ?
N2A C17A 1.349(2) . ?
N2A C21A 1.347(2) . ?
C1A C2A 1.407(2) . ?
C1A C6A 1.409(2) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.382(3) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.397(3) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.380(2) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.398(2) . ?
C7A C8A 1.399(2) . ?
C7A C12A 1.405(2) . ?
C8A H8A 0.9500 . ?
C8A C9A 1.380(2) . ?
C9A H9A 0.9500 . ?
C9A C10A 1.394(2) . ?
C10A H10A 0.9500 . ?
C10A C11A 1.384(2) . ?
C11A H11A 0.9500 . ?
C11A C12A 1.410(2) . ?
C13A H13A 0.9900 . ?
C13A H13B 0.9900 . ?
C13A C14A 1.531(2) . ?
C14A H14A 0.9900 . ?
C14A H14B 0.9900 . ?
C14A C15A 1.524(2) . ?
C15A H15A 0.9900 . ?
C15A H15B 0.9900 . ?
C15A C16A 1.523(2) . ?
C16A H16A 0.9900 . ?
C16A H16B 0.9900 . ?
C17A H17A 0.9500 . ?
C17A C18A 1.375(2) . ?
C18A H18A 0.9500 . ?
C18A C19A 1.381(3) . ?
C19A H19A 0.9500 . ?
C19A C20A 1.386(3) . ?
C20A H20A 0.9500 . ?
C20A C21A 1.376(3) . ?
C21A H21A 0.9500 . ?
S006 O1B 1.4419(15) . ?
S006 O2B 1.4484(17) . ?
S006 C6B 1.7315(19) . ?
S006 C7B 1.7366(19) . ?
N1B C1B 1.401(2) . ?
N1B C12B 1.392(2) . ?
N1B C13B 1.472(2) . ?
N2B C16B 1.487(2) . ?
N2B C17B 1.341(2) . ?
N2B C21B 1.347(2) . ?
C1B C2B 1.407(3) . ?
C1B C6B 1.405(2) . ?
C2B H2B 0.9500 . ?
C2B C3B 1.380(3) . ?
C3B H3B 0.9500 . ?
C3B C4B 1.397(3) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.372(3) . ?
C5B H5B 0.9500 . ?
C5B C6B 1.400(2) . ?
C7B C8B 1.401(3) . ?
C7B C12B 1.409(2) . ?
C8B H8B 0.9500 . ?
C8B C9B 1.374(3) . ?
C9B H9B 0.9500 . ?
C9B C10B 1.395(3) . ?
C10B H10B 0.9500 . ?
C10B C11B 1.381(3) . ?
C11B H11B 0.9500 . ?
C11B C12B 1.411(2) . ?
C13B H13C 0.9900 . ?
C13B H13D 0.9900 . ?
C13B C14B 1.528(2) . ?
C14B H14C 0.9900 . ?
C14B H14D 0.9900 . ?
C14B C15B 1.522(2) . ?
C15B H15C 0.9900 . ?
C15B H15D 0.9900 . ?
C15B C16B 1.517(2) . ?
C16B H16C 0.9900 . ?
C16B H16D 0.9900 . ?
C17B H17B 0.9500 . ?
C17B C18B 1.381(2) . ?
C18B H18B 0.9500 . ?
C18B C19B 1.382(3) . ?
C19B H19B 0.9500 . ?
C19B C20B 1.387(3) . ?
C20B H20B 0.9500 . ?
C20B C21B 1.377(3) . ?
C21B H21B 0.9500 . ?
O1 H1A 0.8498 . ?
O1 H1B 0.8492 . ?

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
Cl1C Cl1A C22 76(5) . . ?
Cl1A Cl1C C22 87(5) . . ?
Cl1A C22 H22A 101.5(15) . . ?
Cl1A C22 H22B 113.2(17) . . ?
Cl1B C22 Cl1A 8.4(5) . . ?
Cl1B C22 Cl2B 109.3(2) . . ?
Cl1B C22 H22A 109.8(14) . . ?
Cl1B C22 H22B 109.8(15) . . ?
Cl1C C22 Cl1A 16.4(10) . . ?
Cl1C C22 Cl1B 8.2(6) . . ?
Cl1C C22 Cl2B 105.9(7) . . ?
Cl1C C22 H22A 117.9(15) . . ?
Cl1C C22 H22B 104.8(16) . . ?
Cl2B C22 Cl1A 113.8(7) . . ?
Cl2B C22 H22A 107.6(14) . . ?
Cl2B C22 H22B 109.5(16) . . ?
Cl2A C22 Cl1A 116.6(9) . . ?
Cl2A C22 Cl1B 111.4(7) . . ?
Cl2A C22 Cl1C 107.2(10) . . ?
Cl2A C22 Cl2B 6.4(5) . . ?
Cl2A C22 H22A 111.6(16) . . ?
Cl2A C22 H22B 103.2(16) . . ?
Cl2C C22 Cl1A 117.2(8) . . ?
Cl2C C22 Cl1B 113.5(5) . . ?
Cl2C C22 Cl1C 110.8(8) . . ?
Cl2C C22 Cl2B 6.8(4) . . ?
Cl2C C22 Cl2A 11.5(10) . . ?
Cl2C C22 H22A 100.9(15) . . ?
Cl2C C22 H22B 111.8(17) . . ?
H22A C22 H22B 111(2) . . ?
O2A S1A O3A 115.84(8) . . ?
O2A S1A C6A 110.65(8) . . ?
O2A S1A C7A 110.50(8) . . ?
O3A S1A C6A 108.54(8) . . ?
O3A S1A C7A 109.71(7) . . ?
C7A S1A C6A 100.49(7) . . ?
C1A N1A C12A 121.46(13) . . ?
C1A N1A C13A 118.49(13) . . ?
C12A N1A C13A 118.44(13) . . ?
C17A N2A C16A 119.54(14) . . ?
C21A N2A C16A 119.03(14) . . ?
C21A N2A C17A 121.43(14) . . ?
N1A C1A C2A 121.86(14) . . ?
N1A C1A C6A 121.62(14) . . ?
C2A C1A C6A 116.52(14) . . ?
C1A C2A H2A 119.6 . . ?
C3A C2A C1A 120.86(15) . . ?
C3A C2A H2A 119.6 . . ?
C2A C3A H3A 119.2 . . ?
C2A C3A C4A 121.60(16) . . ?
C4A C3A H3A 119.2 . . ?
C3A C4A H4A 120.6 . . ?
C5A C4A C3A 118.74(16) . . ?
C5A C4A H4A 120.6 . . ?
C4A C5A H5A 120.1 . . ?
C4A C5A C6A 119.81(15) . . ?
C6A C5A H5A 120.1 . . ?
C1A C6A S1A 118.88(12) . . ?
C5A C6A S1A 118.44(12) . . ?
C5A C6A C1A 122.24(15) . . ?
C8A C7A S1A 118.45(12) . . ?
C8A C7A C12A 122.31(14) . . ?
C12A C7A S1A 118.99(12) . . ?
C7A C8A H8A 120.1 . . ?
C9A C8A C7A 119.86(15) . . ?
C9A C8A H8A 120.1 . . ?
C8A C9A H9A 120.6 . . ?
C8A C9A C10A 118.89(16) . . ?
C10A C9A H9A 120.6 . . ?
C9A C10A H10A 119.3 . . ?
C11A C10A C9A 121.46(15) . . ?
C11A C10A H10A 119.3 . . ?
C10A C11A H11A 119.5 . . ?
C10A C11A C12A 120.97(15) . . ?
C12A C11A H11A 119.5 . . ?
N1A C12A C7A 121.97(14) . . ?
N1A C12A C11A 121.55(14) . . ?
C7A C12A C11A 116.48(14) . . ?
N1A C13A H13A 108.9 . . ?
N1A C13A H13B 108.9 . . ?
N1A C13A C14A 113.25(13) . . ?
H13A C13A H13B 107.7 . . ?
C14A C13A H13A 108.9 . . ?
C14A C13A H13B 108.9 . . ?
C13A C14A H14A 109.3 . . ?
C13A C14A H14B 109.3 . . ?
H14A C14A H14B 107.9 . . ?
C15A C14A C13A 111.82(13) . . ?
C15A C14A H14A 109.3 . . ?
C15A C14A H14B 109.3 . . ?
C14A C15A H15A 110.0 . . ?
C14A C15A H15B 110.0 . . ?
H15A C15A H15B 108.4 . . ?
C16A C15A C14A 108.46(13) . . ?
C16A C15A H15A 110.0 . . ?
C16A C15A H15B 110.0 . . ?
N2A C16A C15A 112.04(13) . . ?
N2A C16A H16A 109.2 . . ?
N2A C16A H16B 109.2 . . ?
C15A C16A H16A 109.2 . . ?
C15A C16A H16B 109.2 . . ?
H16A C16A H16B 107.9 . . ?
N2A C17A H17A 119.7 . . ?
N2A C17A C18A 120.67(16) . . ?
C18A C17A H17A 119.7 . . ?
C17A C18A H18A 120.6 . . ?
C17A C18A C19A 118.83(17) . . ?
C19A C18A H18A 120.6 . . ?
C18A C19A H19A 120.2 . . ?
C18A C19A C20A 119.65(18) . . ?
C20A C19A H19A 120.2 . . ?
C19A C20A H20A 120.1 . . ?
C21A C20A C19A 119.83(19) . . ?
C21A C20A H20A 120.1 . . ?
N2A C21A C20A 119.58(17) . . ?
N2A C21A H21A 120.2 . . ?
C20A C21A H21A 120.2 . . ?
O1B S006 O2B 115.94(10) . . ?
O1B S006 C6B 110.16(10) . . ?
O1B S006 C7B 110.70(10) . . ?
O2B S006 C6B 109.26(9) . . ?
O2B S006 C7B 108.42(10) . . ?
C6B S006 C7B 101.34(9) . . ?
C1B N1B C13B 118.62(14) . . ?
C12B N1B C1B 122.25(14) . . ?
C12B N1B C13B 118.18(14) . . ?
C17B N2B C16B 119.08(15) . . ?
C17B N2B C21B 121.43(16) . . ?
C21B N2B C16B 119.37(16) . . ?
N1B C1B C2B 121.10(15) . . ?
N1B C1B C6B 122.11(16) . . ?
C6B C1B C2B 116.79(16) . . ?
C1B C2B H2B 119.7 . . ?
C3B C2B C1B 120.68(18) . . ?
C3B C2B H2B 119.7 . . ?
C2B C3B H3B 119.2 . . ?
C2B C3B C4B 121.67(19) . . ?
C4B C3B H3B 119.2 . . ?
C3B C4B H4B 120.6 . . ?
C5B C4B C3B 118.78(18) . . ?
C5B C4B H4B 120.6 . . ?
C4B C5B H5B 120.0 . . ?
C4B C5B C6B 120.06(18) . . ?
C6B C5B H5B 120.0 . . ?
C1B C6B S006 119.75(14) . . ?
C5B C6B S006 118.04(14) . . ?
C5B C6B C1B 122.01(17) . . ?
C8B C7B S006 118.18(15) . . ?
C8B C7B C12B 121.94(18) . . ?
C12B C7B S006 119.48(14) . . ?
C7B C8B H8B 119.9 . . ?
C9B C8B C7B 120.3(2) . . ?
C9B C8B H8B 119.9 . . ?
C8B C9B H9B 120.6 . . ?
C8B C9B C10B 118.7(2) . . ?
C10B C9B H9B 120.6 . . ?
C9B C10B H10B 119.2 . . ?
C11B C10B C9B 121.6(2) . . ?
C11B C10B H10B 119.2 . . ?
C10B C11B H11B 119.5 . . ?
C10B C11B C12B 120.97(18) . . ?
C12B C11B H11B 119.5 . . ?
N1B C12B C7B 121.86(16) . . ?
N1B C12B C11B 121.72(16) . . ?
C7B C12B C11B 116.41(17) . . ?
N1B C13B H13C 108.6 . . ?
N1B C13B H13D 108.6 . . ?
N1B C13B C14B 114.50(14) . . ?
H13C C13B H13D 107.6 . . ?
C14B C13B H13C 108.6 . . ?
C14B C13B H13D 108.6 . . ?
C13B C14B H14C 109.7 . . ?
C13B C14B H14D 109.7 . . ?
H14C C14B H14D 108.2 . . ?
C15B C14B C13B 109.71(13) . . ?
C15B C14B H14C 109.7 . . ?
C15B C14B H14D 109.7 . . ?
C14B C15B H15C 109.4 . . ?
C14B C15B H15D 109.4 . . ?
H15C C15B H15D 108.0 . . ?
C16B C15B C14B 111.15(14) . . ?
C16B C15B H15C 109.4 . . ?
C16B C15B H15D 109.4 . . ?
N2B C16B C15B 109.24(13) . . ?
N2B C16B H16C 109.8 . . ?
N2B C16B H16D 109.8 . . ?
C15B C16B H16C 109.8 . . ?
C15B C16B H16D 109.8 . . ?
H16C C16B H16D 108.3 . . ?
N2B C17B H17B 119.9 . . ?
N2B C17B C18B 120.25(17) . . ?
C18B C17B H17B 119.9 . . ?
C17B C18B H18B 120.3 . . ?
C17B C18B C19B 119.35(19) . . ?
C19B C18B H18B 120.3 . . ?
C18B C19B H19B 120.3 . . ?
C18B C19B C20B 119.45(17) . . ?
C20B C19B H19B 120.3 . . ?
C19B C20B H20B 120.4 . . ?
C21B C20B C19B 119.25(18) . . ?
C21B C20B H20B 120.4 . . ?
N2B C21B C20B 120.24(19) . . ?
N2B C21B H21B 119.9 . . ?
C20B C21B H21B 119.9 . . ?
H1A O1 H1B 109.5 . . ?

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
Cl1A Cl1C C22 Cl1B -5.6(19) . . . . ?
Cl1A Cl1C C22 Cl2B -121(4) . . . . ?
Cl1A Cl1C C22 Cl2A -128(4) . . . . ?
Cl1A Cl1C C22 Cl2C -116(4) . . . . ?
Cl1C Cl1A C22 Cl1B 5.4(18) . . . . ?
Cl1C Cl1A C22 Cl2B 64(4) . . . . ?
Cl1C Cl1A C22 Cl2A 58(4) . . . . ?
Cl1C Cl1A C22 Cl2C 71(4) . . . . ?
S1A C7A C8A C9A -173.84(12) . . . . ?
S1A C7A C12A N1A -8.1(2) . . . . ?
S1A C7A C12A C11A 172.51(12) . . . . ?
O2A S1A C6A C1A -154.24(12) . . . . ?
O2A S1A C6A C5A 33.17(16) . . . . ?
O2A S1A C7A C8A -33.90(15) . . . . ?
O2A S1A C7A C12A 151.67(12) . . . . ?
O3A S1A C6A C1A 77.61(14) . . . . ?
O3A S1A C6A C5A -94.98(14) . . . . ?
O3A S1A C7A C8A 95.02(13) . . . . ?
O3A S1A C7A C12A -79.41(14) . . . . ?
N1A C1A C2A C3A 175.60(15) . . . . ?
N1A C1A C6A S1A 13.5(2) . . . . ?
N1A C1A C6A C5A -174.22(15) . . . . ?
N1A C13A C14A C15A 178.68(14) . . . . ?
N2A C17A C18A C19A 0.0(3) . . . . ?
C1A N1A C12A C7A -25.3(2) . . . . ?
C1A N1A C12A C11A 154.04(15) . . . . ?
C1A N1A C13A C14A -81.62(18) . . . . ?
C1A C2A C3A C4A -0.6(3) . . . . ?
C2A C1A C6A S1A -167.41(12) . . . . ?
C2A C1A C6A C5A 4.9(2) . . . . ?
C2A C3A C4A C5A 3.6(3) . . . . ?
C3A C4A C5A C6A -2.2(3) . . . . ?
C4A C5A C6A S1A 170.24(13) . . . . ?
C4A C5A C6A C1A -2.1(3) . . . . ?
C6A S1A C7A C8A -150.79(13) . . . . ?
C6A S1A C7A C12A 34.79(14) . . . . ?
C6A C1A C2A C3A -3.5(2) . . . . ?
C7A S1A C6A C1A -37.47(14) . . . . ?
C7A S1A C6A C5A 149.94(13) . . . . ?
C7A C8A C9A C10A 0.8(2) . . . . ?
C8A C7A C12A N1A 177.66(14) . . . . ?
C8A C7A C12A C11A -1.7(2) . . . . ?
C8A C9A C10A C11A -0.7(2) . . . . ?
C9A C10A C11A C12A -0.7(3) . . . . ?
C10A C11A C12A N1A -177.54(15) . . . . ?
C10A C11A C12A C7A 1.8(2) . . . . ?
C12A N1A C1A C2A -156.76(15) . . . . ?
C12A N1A C1A C6A 22.3(2) . . . . ?
C12A N1A C13A C14A 84.10(18) . . . . ?
C12A C7A C8A C9A 0.4(2) . . . . ?
C13A N1A C1A C2A 8.5(2) . . . . ?
C13A N1A C1A C6A -172.43(14) . . . . ?
C13A N1A C12A C7A 169.44(14) . . . . ?
C13A N1A C12A C11A -11.2(2) . . . . ?
C13A C14A C15A C16A 175.39(14) . . . . ?
C14A C15A C16A N2A 179.41(13) . . . . ?
C16A N2A C17A C18A 179.62(17) . . . . ?
C16A N2A C21A C20A -179.7(2) . . . . ?
C17A N2A C16A C15A 77.41(19) . . . . ?
C17A N2A C21A C20A 0.6(3) . . . . ?
C17A C18A C19A C20A 0.5(4) . . . . ?
C18A C19A C20A C21A -0.6(4) . . . . ?
C19A C20A C21A N2A 0.0(4) . . . . ?
C21A N2A C16A C15A -102.38(19) . . . . ?
C21A N2A C17A C18A -0.6(3) . . . . ?
S006 C7B C8B C9B -170.3(2) . . . . ?
S006 C7B C12B N1B -11.9(3) . . . . ?
S006 C7B C12B C11B 169.15(16) . . . . ?
O1B S006 C6B C1B -148.07(14) . . . . ?
O1B S006 C6B C5B 37.07(17) . . . . ?
O1B S006 C7B C8B -36.9(2) . . . . ?
O1B S006 C7B C12B 150.23(18) . . . . ?
O2B S006 C6B C1B 83.47(16) . . . . ?
O2B S006 C6B C5B -91.39(15) . . . . ?
O2B S006 C7B C8B 91.3(2) . . . . ?
O2B S006 C7B C12B -81.54(19) . . . . ?
N1B C1B C2B C3B 178.19(17) . . . . ?
N1B C1B C6B S006 6.7(2) . . . . ?
N1B C1B C6B C5B -178.59(16) . . . . ?
N1B C13B C14B C15B -169.26(14) . . . . ?
N2B C17B C18B C19B -1.0(3) . . . . ?
C1B N1B C12B C7B -20.5(3) . . . . ?
C1B N1B C12B C11B 158.41(18) . . . . ?
C1B N1B C13B C14B -87.04(19) . . . . ?
C1B C2B C3B C4B 0.7(3) . . . . ?
C2B C1B C6B S006 -173.81(13) . . . . ?
C2B C1B C6B C5B 0.8(3) . . . . ?
C2B C3B C4B C5B 0.4(3) . . . . ?
C3B C4B C5B C6B -0.8(3) . . . . ?
C4B C5B C6B S006 174.91(14) . . . . ?
C4B C5B C6B C1B 0.2(3) . . . . ?
C6B S006 C7B C8B -153.8(2) . . . . ?
C6B S006 C7B C12B 33.4(2) . . . . ?
C6B C1B C2B C3B -1.3(3) . . . . ?
C7B S006 C6B C1B -30.83(17) . . . . ?
C7B S006 C6B C5B 154.31(15) . . . . ?
C7B C8B C9B C10B 0.5(4) . . . . ?
C8B C7B C12B N1B 175.5(2) . . . . ?
C8B C7B C12B C11B -3.4(3) . . . . ?
C8B C9B C10B C11B -2.3(4) . . . . ?
C9B C10B C11B C12B 1.1(4) . . . . ?
C10B C11B C12B N1B -177.3(2) . . . . ?
C10B C11B C12B C7B 1.7(3) . . . . ?
C12B N1B C1B C2B -156.05(17) . . . . ?
C12B N1B C1B C6B 23.4(3) . . . . ?
C12B N1B C13B C14B 82.1(2) . . . . ?
C12B C7B C8B C9B 2.4(4) . . . . ?
C13B N1B C1B C2B 12.6(2) . . . . ?
C13B N1B C1B C6B -168.01(15) . . . . ?
C13B N1B C12B C7B 170.88(17) . . . . ?
C13B N1B C12B C11B -10.3(3) . . . . ?
C13B C14B C15B C16B -178.80(15) . . . . ?
C14B C15B C16B N2B -175.21(14) . . . . ?
C16B N2B C17B C18B -175.57(16) . . . . ?
C16B N2B C21B C20B 176.92(16) . . . . ?
C17B N2B C16B C15B 96.16(18) . . . . ?
C17B N2B C21B C20B 1.0(3) . . . . ?
C17B C18B C19B C20B 0.2(3) . . . . ?
C18B C19B C20B C21B 1.1(3) . . . . ?
C19B C20B C21B N2B -1.7(3) . . . . ?
C21B N2B C16B C15B -79.83(19) . . . . ?
C21B N2B C17B C18B 0.3(3) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.500 0.500 112.2 27.6 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mw363_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2024266'
loop_
_audit_author_name
_audit_author_address
'Duane Hean'
;University of British Columbia
Canada
;
_audit_update_record             
;
2020-08-19 deposited with the CCDC.	2021-07-28 downloaded from the CCDC.
;
_audit_creation_date             2019-10-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H21 N2, I'
_chemical_formula_sum            'C21 H21 I N2'
_chemical_formula_weight         428.30
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   15.18(3)
_cell_length_b                   9.822(16)
_cell_length_c                   24.70(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3683(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7764
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      30.50
_cell_measurement_theta_min      2.97
_shelx_estimated_absorpt_T_max   0.918
_shelx_estimated_absorpt_T_min   0.552
_exptl_absorpt_coefficient_mu    1.743
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6066
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1552 before and 0.0553 after correction. The Ratio of minimum to maximum transmission is 0.8130. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.387
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            23735
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.588
_diffrn_reflns_theta_min         1.649
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4136
_reflns_number_total             5619
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         1.032
_refine_diff_density_min         -0.911
_refine_diff_density_rms         0.123
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         5619
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0422
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0496P)²+4.6280P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1138
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(I1B) = Uanis(I1A)
3. Others
 Sof(I1B)=1-FVAR(1)
 Sof(I1A)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C17(H17),
 C18(H18), C19(H19), C20(H20), C21(H21)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
N1 N 0.17206(15) 0.6367(3) 0.23963(10) 0.0181(5) Uani 1 1 d . . . . .
N2 N 0.45444(16) 0.4873(3) 0.41329(10) 0.0157(5) Uani 1 1 d . . . . .
C1 C 0.17958(18) 0.6877(3) 0.18776(13) 0.0197(6) Uani 1 1 d . . . . .
C2 C 0.2412(2) 0.6561(4) 0.14771(15) 0.0289(8) Uani 1 1 d . . . . .
H2 H 0.287229 0.592522 0.154154 0.035 Uiso 1 1 calc R . . . .
C3 C 0.2327(2) 0.7210(4) 0.09827(15) 0.0338(9) Uani 1 1 d . . . . .
H3 H 0.273379 0.700232 0.070249 0.041 Uiso 1 1 calc R . . . .
C4 C 0.1662(2) 0.8161(4) 0.08816(14) 0.0322(8) Uani 1 1 d . . . . .
H4 H 0.163649 0.860824 0.054106 0.039 Uiso 1 1 calc R . . . .
C5 C 0.1043(2) 0.8453(3) 0.12740(13) 0.0238(7) Uani 1 1 d . . . . .
H5 H 0.058629 0.909083 0.120521 0.029 Uiso 1 1 calc R . . . .
C6 C 0.11013(18) 0.7794(3) 0.17751(12) 0.0175(6) Uani 1 1 d . . . . .
C7 C 0.05644(18) 0.7808(3) 0.22567(12) 0.0154(5) Uani 1 1 d . . . . .
C8 C -0.02263(19) 0.8433(3) 0.23931(13) 0.0183(6) Uani 1 1 d . . . . .
H8 H -0.051004 0.902821 0.214506 0.022 Uiso 1 1 calc R . . . .
C9 C -0.05919(19) 0.8178(3) 0.28920(13) 0.0210(6) Uani 1 1 d . . . . .
H9 H -0.113286 0.860035 0.298790 0.025 Uiso 1 1 calc R . . . .
C10 C -0.01804(18) 0.7310(3) 0.32586(13) 0.0187(6) Uani 1 1 d . . . . .
H10 H -0.045034 0.714781 0.359948 0.022 Uiso 1 1 calc R . . . .
C11 C 0.06132(18) 0.6675(3) 0.31401(12) 0.0165(6) Uani 1 1 d . . . . .
H11 H 0.089889 0.609991 0.339477 0.020 Uiso 1 1 calc R . . . .
C12 C 0.09706(18) 0.6920(3) 0.26307(12) 0.0150(5) Uani 1 1 d . . . . .
C13 C 0.23325(19) 0.5460(3) 0.26673(14) 0.0210(6) Uani 1 1 d . . . . .
H13A H 0.270975 0.501332 0.239273 0.025 Uiso 1 1 calc R . . . .
H13B H 0.199574 0.473930 0.285646 0.025 Uiso 1 1 calc R . . . .
C14 C 0.29171(17) 0.6194(3) 0.30758(12) 0.0168(6) Uani 1 1 d . . . . .
H14A H 0.324896 0.692677 0.289092 0.020 Uiso 1 1 calc R . . . .
H14B H 0.254562 0.661729 0.335897 0.020 Uiso 1 1 calc R . . . .
C15 C 0.35607(19) 0.5200(3) 0.33371(13) 0.0183(6) Uani 1 1 d . . . . .
H15A H 0.324905 0.434852 0.343362 0.022 Uiso 1 1 calc R . . . .
H15B H 0.403483 0.497136 0.307736 0.022 Uiso 1 1 calc R . . . .
C16 C 0.39575(19) 0.5831(3) 0.38419(13) 0.0190(6) Uani 1 1 d . . . . .
H16A H 0.429732 0.665128 0.373895 0.023 Uiso 1 1 calc R . . . .
H16B H 0.347718 0.612057 0.408722 0.023 Uiso 1 1 calc R . . . .
C17 C 0.5406(2) 0.5139(3) 0.41680(14) 0.0204(6) Uani 1 1 d . . . . .
H17 H 0.564359 0.590872 0.398656 0.025 Uiso 1 1 calc R . . . .
C18 C 0.5954(2) 0.4301(4) 0.44668(13) 0.0239(7) Uani 1 1 d . . . . .
H18 H 0.656315 0.450882 0.450021 0.029 Uiso 1 1 calc R . . . .
C19 C 0.5609(2) 0.3157(4) 0.47168(13) 0.0244(7) Uani 1 1 d . . . . .
H19 H 0.597628 0.257156 0.492329 0.029 Uiso 1 1 calc R . . . .
C20 C 0.4717(2) 0.2880(4) 0.46609(13) 0.0260(7) Uani 1 1 d . . . . .
H20 H 0.446907 0.209377 0.482548 0.031 Uiso 1 1 calc R . . . .
C21 C 0.4194(2) 0.3749(4) 0.43661(12) 0.0223(6) Uani 1 1 d . . . . .
H21 H 0.358352 0.356071 0.432573 0.027 Uiso 1 1 calc R . . . .
I1A I 0.16880(2) 1.04055(2) -0.06014(2) 0.02691(9) Uani 0.9866(6) 1 d . . P A 1
I1B I 0.1385(11) 1.0820(18) -0.0916(8) 0.02691(9) Uani 0.0134(6) 1 d . . P A 2


_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 C1 1.380(5) . ?
N1 C12 1.388(4) . ?
N1 C13 1.451(4) . ?
N2 C16 1.482(4) . ?
N2 C17 1.337(4) . ?
N2 C21 1.354(4) . ?
C1 C2 1.397(5) . ?
C1 C6 1.410(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.384(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.397(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.380(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.400(5) . ?
C6 C7 1.442(4) . ?
C7 C8 1.390(4) . ?
C7 C12 1.412(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.375(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.392(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.388(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.391(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.525(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.525(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.517(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17 0.9500 . ?
C17 C18 1.384(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.386(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.388(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.375(5) . ?
C21 H21 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
C1 N1 C12 108.3(2) . . ?
C1 N1 C13 126.7(3) . . ?
C12 N1 C13 125.0(3) . . ?
C17 N2 C16 119.7(3) . . ?
C17 N2 C21 121.1(3) . . ?
C21 N2 C16 119.2(3) . . ?
N1 C1 C2 129.2(3) . . ?
N1 C1 C6 109.7(3) . . ?
C2 C1 C6 121.1(3) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 C1 117.4(4) . . ?
C3 C2 H2 121.3 . . ?
C2 C3 H3 118.9 . . ?
C2 C3 C4 122.2(3) . . ?
C4 C3 H3 118.9 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.3(3) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.6 . . ?
C4 C5 C6 118.8(3) . . ?
C6 C5 H5 120.6 . . ?
C1 C6 C7 106.3(3) . . ?
C5 C6 C1 120.1(3) . . ?
C5 C6 C7 133.6(3) . . ?
C8 C7 C6 133.8(3) . . ?
C8 C7 C12 119.4(3) . . ?
C12 C7 C6 106.7(3) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 C7 119.0(3) . . ?
C9 C8 H8 120.5 . . ?
C8 C9 H9 119.5 . . ?
C8 C9 C10 120.9(3) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 119.1 . . ?
C11 C10 C9 121.9(3) . . ?
C11 C10 H10 119.1 . . ?
C10 C11 H11 121.6 . . ?
C10 C11 C12 116.8(3) . . ?
C12 C11 H11 121.6 . . ?
N1 C12 C7 109.1(3) . . ?
N1 C12 C11 129.0(3) . . ?
C11 C12 C7 121.9(3) . . ?
N1 C13 H13A 109.0 . . ?
N1 C13 H13B 109.0 . . ?
N1 C13 C14 112.8(3) . . ?
H13A C13 H13B 107.8 . . ?
C14 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
C13 C14 H14A 109.6 . . ?
C13 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C15 C14 C13 110.5(3) . . ?
C15 C14 H14A 109.6 . . ?
C15 C14 H14B 109.6 . . ?
C14 C15 H15A 109.7 . . ?
C14 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
C16 C15 C14 109.9(3) . . ?
C16 C15 H15A 109.7 . . ?
C16 C15 H15B 109.7 . . ?
N2 C16 C15 112.2(3) . . ?
N2 C16 H16A 109.2 . . ?
N2 C16 H16B 109.2 . . ?
C15 C16 H16A 109.2 . . ?
C15 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
N2 C17 H17 119.8 . . ?
N2 C17 C18 120.4(3) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 120.3 . . ?
C17 C18 C19 119.5(3) . . ?
C19 C18 H18 120.3 . . ?
C18 C19 H19 120.5 . . ?
C18 C19 C20 119.0(3) . . ?
C20 C19 H19 120.5 . . ?
C19 C20 H20 120.2 . . ?
C21 C20 C19 119.6(3) . . ?
C21 C20 H20 120.2 . . ?
N2 C21 C20 120.3(3) . . ?
N2 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mw357_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2024267'
loop_
_audit_author_name
_audit_author_address
'Duane Hean'
;University of British Columbia
Canada
;
_audit_update_record             
;
2020-08-19 deposited with the CCDC.	2021-07-28 downloaded from the CCDC.
;
_audit_creation_date             2019-10-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H23 N2, Br, H0.99 O0.62'
_chemical_formula_sum            'C25 H23.99 Br N2 O0.62'
_chemical_formula_weight         442.20
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   10.1665(7)
_cell_length_b                   16.1182(13)
_cell_length_c                   13.0048(11)
_cell_angle_alpha                90
_cell_angle_beta                 99.468(4)
_cell_angle_gamma                90
_cell_volume                     2102.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6036
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      25.784
_cell_measurement_theta_min      2.363
_shelx_estimated_absorpt_T_max   0.874
_shelx_estimated_absorpt_T_min   0.589
_exptl_absorpt_coefficient_mu    1.972
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0981 before and 0.0490 after correction. The Ratio of minimum to maximum transmission is 0.8453. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17071
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.395
_diffrn_reflns_theta_min         2.029
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3023
_reflns_number_total             4277
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         1.164
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         4277
_refine_ls_number_restraints     813
_refine_ls_R_factor_all          0.0949
_refine_ls_R_factor_gt           0.0637
_refine_ls_restrained_S_all      0.968
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0653P)²+3.5430P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1535
_refine_ls_wR_factor_ref         0.1666
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(H15C)=Sof(H15D)=Sof(N2B)=Sof(C16B)=Sof(H16C)=Sof(H16D)=Sof(C17B)=
 Sof(H17B)=Sof(C18B)=Sof(H18B)=Sof(C19B)=Sof(H19B)=Sof(C25B)=Sof(C20B)=
 Sof(C21B)=Sof(H21B)=Sof(C22B)=Sof(H22B)=Sof(C23B)=Sof(H23B)=Sof(C24B)=
 Sof(H24B)=1-FVAR(1)
 Sof(H15A)=Sof(H15B)=Sof(N2A)=Sof(C16A)=Sof(H16A)=Sof(H16B)=Sof(C17A)=
 Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(H20A)=Sof(C21A)=
 Sof(H21A)=Sof(C22A)=Sof(C23A)=Sof(H23A)=Sof(C24A)=Sof(H24A)=Sof(C25A)=
 Sof(H25A)=FVAR(1)
 Sof(Br1A)=Sof(O1)=1-FVAR(2)
 Sof(Br1B)=FVAR(2)
 Sof(H1A)=Sof(H1B)=FVAR(3)
5.a Free rotating group:
 O1(H1A,H1B)
5.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C15(H15C,H15D), C16A(H16A,
 H16B), C16B(H16C,H16D)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11),
 C18A(H18A), C19A(H19A), C20A(H20A), C21A(H21A), C23A(H23A), C24A(H24A),
 C25A(H25A), C17B(H17B), C18B(H18B), C19B(H19B), C21B(H21B), C22B(H22B),
 C23B(H23B), C24B(H24B)
5.d Fitted hexagon refined as free rotating group:
 C25B(C20B,C21B,C22B,C23B,C24B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
N1 N 0.3670(3) 0.69470(18) 0.1881(2) 0.0249(6) Uani 1 1 d . U . . .
C1 C 0.3104(3) 0.6765(2) 0.2749(3) 0.0245(7) Uani 1 1 d . U . . .
C2 C 0.3428(4) 0.6136(2) 0.3482(3) 0.0321(8) Uani 1 1 d . U . . .
H2 H 0.412944 0.575620 0.343505 0.039 Uiso 1 1 calc R . . . .
C3 C 0.2684(4) 0.6088(3) 0.4285(3) 0.0398(10) Uani 1 1 d . U . . .
H3 H 0.287360 0.566208 0.479235 0.048 Uiso 1 1 calc R . . . .
C4 C 0.1658(4) 0.6654(2) 0.4362(3) 0.0384(10) Uani 1 1 d . U . . .
H4 H 0.116352 0.660359 0.491795 0.046 Uiso 1 1 calc R . . . .
C5 C 0.1358(4) 0.7281(2) 0.3646(3) 0.0307(8) Uani 1 1 d . U . . .
H5 H 0.067567 0.766992 0.371643 0.037 Uiso 1 1 calc R . . . .
C6 C 0.2066(3) 0.7341(2) 0.2813(3) 0.0245(7) Uani 1 1 d . U . . .
C7 C 0.1995(3) 0.7880(2) 0.1922(3) 0.0241(7) Uani 1 1 d . U . . .
C8 C 0.1166(4) 0.8543(2) 0.1527(3) 0.0285(8) Uani 1 1 d . U . . .
H8 H 0.047123 0.872588 0.187901 0.034 Uiso 1 1 calc R . . . .
C9 C 0.1378(4) 0.8919(2) 0.0629(3) 0.0334(9) Uani 1 1 d . U . . .
H9 H 0.082124 0.936852 0.036021 0.040 Uiso 1 1 calc R . . . .
C10 C 0.2395(4) 0.8662(2) 0.0092(3) 0.0364(9) Uani 1 1 d . U . . .
H10 H 0.251430 0.893967 -0.053065 0.044 Uiso 1 1 calc R . . . .
C11 C 0.3224(4) 0.8010(2) 0.0455(3) 0.0299(8) Uani 1 1 d . U . . .
H11 H 0.391169 0.783152 0.009228 0.036 Uiso 1 1 calc R . . . .
C12 C 0.3015(3) 0.7623(2) 0.1373(3) 0.0252(7) Uani 1 1 d . U . . .
C13 C 0.4759(3) 0.6498(2) 0.1522(3) 0.0283(8) Uani 1 1 d . U . . .
H13A H 0.459250 0.648031 0.075103 0.034 Uiso 1 1 calc R . . . .
H13B H 0.477024 0.591968 0.177954 0.034 Uiso 1 1 calc R . . . .
C14 C 0.6119(3) 0.6890(2) 0.1890(3) 0.0264(8) Uani 1 1 d . U . . .
H14A H 0.607556 0.749222 0.173682 0.032 Uiso 1 1 calc R . . . .
H14B H 0.636685 0.681952 0.265379 0.032 Uiso 1 1 calc R . . . .
C15 C 0.7172(3) 0.6490(2) 0.1348(3) 0.0328(9) Uani 1 1 d . U . . .
H15A H 0.731601 0.590958 0.159042 0.039 Uiso 0.646(5) 1 calc R . P A 1
H15B H 0.685238 0.647848 0.058640 0.039 Uiso 0.646(5) 1 calc R . P A 1
H15C H 0.714929 0.673697 0.064799 0.039 Uiso 0.354(5) 1 calc R . P A 2
H15D H 0.700062 0.588692 0.126311 0.039 Uiso 0.354(5) 1 calc R . P A 2
N2A N 0.9441(4) 0.6700(3) 0.0872(3) 0.0213(11) Uani 0.646(5) 1 d . U P A 1
C16A C 0.8480(6) 0.6957(4) 0.1567(5) 0.0260(13) Uani 0.646(5) 1 d . U P A 1
H16A H 0.830042 0.755880 0.147570 0.031 Uiso 0.646(5) 1 calc R . P A 1
H16B H 0.889343 0.686368 0.230148 0.031 Uiso 0.646(5) 1 calc R . P A 1
C17A C 1.0226(7) 0.6005(5) 0.1099(6) 0.0179(16) Uani 0.646(5) 1 d . U P A 1
C18A C 1.0146(6) 0.5485(4) 0.1960(5) 0.0253(13) Uani 0.646(5) 1 d . U P A 1
H18A H 0.950952 0.559416 0.240234 0.030 Uiso 0.646(5) 1 calc R . P A 1
C19A C 1.1004(18) 0.4813(10) 0.2156(10) 0.027(3) Uani 0.646(5) 1 d . U P A 1
H19A H 1.096052 0.446369 0.273802 0.032 Uiso 0.646(5) 1 calc R . P A 1
C20A C 1.1930(9) 0.4649(5) 0.1501(7) 0.0282(16) Uani 0.646(5) 1 d . U P A 1
H20A H 1.251666 0.419027 0.165110 0.034 Uiso 0.646(5) 1 calc R . P A 1
C21A C 1.2019(5) 0.5128(3) 0.0651(4) 0.0259(13) Uani 0.646(5) 1 d . U P A 1
H21A H 1.266135 0.500270 0.021951 0.031 Uiso 0.646(5) 1 calc R . P A 1
C22A C 1.1154(7) 0.5812(4) 0.0413(5) 0.0229(14) Uani 0.646(5) 1 d . U P A 1
C23A C 1.1184(7) 0.6310(4) -0.0471(5) 0.0261(14) Uani 0.646(5) 1 d . U P A 1
H23A H 1.178941 0.619129 -0.093560 0.031 Uiso 0.646(5) 1 calc R . P A 1
C24A C 1.0332(9) 0.6961(6) -0.0650(7) 0.0283(19) Uani 0.646(5) 1 d . U P A 1
H24A H 1.032794 0.729303 -0.125478 0.034 Uiso 0.646(5) 1 calc R . P A 1
C25A C 0.9484(6) 0.7147(4) 0.0025(4) 0.0234(12) Uani 0.646(5) 1 d . U P A 1
H25A H 0.890574 0.761040 -0.011572 0.028 Uiso 0.646(5) 1 calc R . P A 1
N2B N 0.9674(8) 0.6065(5) 0.1845(6) 0.025(2) Uani 0.354(5) 1 d . U P A 2
C16B C 0.8616(11) 0.6647(8) 0.2058(9) 0.028(2) Uani 0.354(5) 1 d . U P A 2
H16C H 0.890240 0.722157 0.194157 0.033 Uiso 0.354(5) 1 calc R . P A 2
H16D H 0.852192 0.659779 0.280157 0.033 Uiso 0.354(5) 1 calc R . P A 2
C17B C 1.0039(11) 0.5466(7) 0.2531(10) 0.030(2) Uani 0.354(5) 1 d . U P A 2
H17B H 0.961187 0.542532 0.312650 0.036 Uiso 0.354(5) 1 calc R . P A 2
C18B C 1.100(4) 0.491(2) 0.241(2) 0.034(5) Uani 0.354(5) 1 d . U P A 2
H18B H 1.122234 0.448834 0.291863 0.040 Uiso 0.354(5) 1 calc R . P A 2
C19B C 1.1647(16) 0.4945(9) 0.1575(14) 0.031(3) Uani 0.354(5) 1 d . U P A 2
H19B H 1.233373 0.456104 0.150185 0.037 Uiso 0.354(5) 1 calc R . P A 2
C25B C 1.0250(10) 0.6133(6) 0.0936(6) 0.021(3) Uani 0.354(5) 1 d . U P A 2
C20B C 1.1261(9) 0.5583(5) 0.0803(6) 0.022(2) Uani 0.354(5) 1 d G U P A 2
C21B C 1.1871(7) 0.5640(5) -0.0076(6) 0.029(2) Uani 0.354(5) 1 d G U P A 2
H21B H 1.256262 0.526365 -0.016685 0.035 Uiso 0.354(5) 1 calc R . P A 2
C22B C 1.1470(10) 0.6246(6) -0.0822(6) 0.028(3) Uani 0.354(5) 1 d G U P A 2
H22B H 1.188641 0.628439 -0.142222 0.034 Uiso 0.354(5) 1 calc R . P A 2
C23B C 1.0458(11) 0.6796(6) -0.0689(7) 0.027(4) Uani 0.354(5) 1 d G U P A 2
H23B H 1.018336 0.721023 -0.119817 0.033 Uiso 0.354(5) 1 calc R . P A 2
C24B C 0.9848(8) 0.6739(5) 0.0190(7) 0.025(2) Uani 0.354(5) 1 d G U P A 2
H24B H 0.915651 0.711533 0.028124 0.031 Uiso 0.354(5) 1 calc R . P A 2
Br1B Br -0.05593(19) 0.93026(9) 0.37710(15) 0.0418(5) Uani 0.384(2) 1 d . U P B
1
Br1A Br -0.20832(8) 0.95189(5) 0.20146(6) 0.0554(3) Uani 0.616(2) 1 d . U P B 2
O1 O 0.0095(9) 0.9280(5) 0.4145(6) 0.056(2) Uani 0.616(2) 1 d . U P B 2
H1A H -0.004110 0.963003 0.462621 0.084 Uiso 0.49(7) 1 d G . P C 2
H1B H -0.017700 0.949537 0.353412 0.084 Uiso 0.49(7) 1 d G . P C 2


_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 C1 1.380(4) . ?
N1 C12 1.387(4) . ?
N1 C13 1.462(4) . ?
C1 C2 1.393(5) . ?
C1 C6 1.418(5) . ?
C2 C3 1.388(5) . ?
C3 C4 1.401(5) . ?
C4 C5 1.374(5) . ?
C5 C6 1.400(5) . ?
C6 C7 1.441(5) . ?
C7 C8 1.405(5) . ?
C7 C12 1.413(5) . ?
C8 C9 1.364(5) . ?
C9 C10 1.402(6) . ?
C10 C11 1.381(5) . ?
C11 C12 1.394(5) . ?
C13 C14 1.524(5) . ?
C14 C15 1.520(4) . ?
C15 C16A 1.514(7) . ?
C15 C16B 1.620(12) . ?
N2A C16A 1.495(7) . ?
N2A C17A 1.379(8) . ?
N2A C25A 1.322(7) . ?
C17A C18A 1.412(10) . ?
C17A C22A 1.435(8) . ?
C18A C19A 1.387(16) . ?
C19A C20A 1.396(12) . ?
C20A C21A 1.364(10) . ?
C21A C22A 1.411(8) . ?
C22A C23A 1.407(9) . ?
C23A C24A 1.357(9) . ?
C24A C25A 1.362(9) . ?
N2B C16B 1.488(13) . ?
N2B C17B 1.326(14) . ?
N2B C25B 1.406(9) . ?
C17B C18B 1.35(3) . ?
C18B C19B 1.36(2) . ?
C19B C20B 1.445(17) . ?
C25B C20B 1.3900 . ?
C25B C24B 1.3900 . ?
C20B C21B 1.3900 . ?
C21B C22B 1.3900 . ?
C22B C23B 1.3900 . ?
C23B C24B 1.3900 . ?

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
C1 N1 C12 108.9(3) . . ?
C1 N1 C13 126.5(3) . . ?
C12 N1 C13 124.5(3) . . ?
N1 C1 C2 129.1(3) . . ?
N1 C1 C6 108.9(3) . . ?
C2 C1 C6 122.0(3) . . ?
C3 C2 C1 117.3(3) . . ?
C2 C3 C4 121.4(4) . . ?
C5 C4 C3 121.1(3) . . ?
C4 C5 C6 119.3(3) . . ?
C1 C6 C7 106.6(3) . . ?
C5 C6 C1 118.9(3) . . ?
C5 C6 C7 134.5(3) . . ?
C8 C7 C6 134.4(3) . . ?
C8 C7 C12 118.9(3) . . ?
C12 C7 C6 106.6(3) . . ?
C9 C8 C7 118.8(3) . . ?
C8 C9 C10 121.9(4) . . ?
C11 C10 C9 120.9(4) . . ?
C10 C11 C12 117.6(3) . . ?
N1 C12 C7 108.9(3) . . ?
N1 C12 C11 129.1(3) . . ?
C11 C12 C7 122.0(3) . . ?
N1 C13 C14 113.0(3) . . ?
C15 C14 C13 110.5(3) . . ?
C14 C15 C16B 108.0(4) . . ?
C16A C15 C14 111.4(3) . . ?
C17A N2A C16A 120.6(5) . . ?
C25A N2A C16A 117.8(5) . . ?
C25A N2A C17A 121.6(5) . . ?
N2A C16A C15 112.9(4) . . ?
N2A C17A C18A 123.0(6) . . ?
N2A C17A C22A 117.4(6) . . ?
C18A C17A C22A 119.6(6) . . ?
C19A C18A C17A 119.5(7) . . ?
C18A C19A C20A 120.2(11) . . ?
C21A C20A C19A 122.0(9) . . ?
C20A C21A C22A 119.8(6) . . ?
C21A C22A C17A 118.9(6) . . ?
C23A C22A C17A 119.3(6) . . ?
C23A C22A C21A 121.9(6) . . ?
C24A C23A C22A 118.9(6) . . ?
C23A C24A C25A 120.9(7) . . ?
N2A C25A C24A 121.9(6) . . ?
C17B N2B C16B 117.6(9) . . ?
C17B N2B C25B 120.9(9) . . ?
C25B N2B C16B 121.4(9) . . ?
N2B C16B C15 114.2(8) . . ?
N2B C17B C18B 122.1(16) . . ?
C17B C18B C19B 121(2) . . ?
C18B C19B C20B 118.1(17) . . ?
C20B C25B N2B 118.3(6) . . ?
C20B C25B C24B 120.0 . . ?
C24B C25B N2B 121.7(6) . . ?
C25B C20B C19B 119.3(8) . . ?
C21B C20B C19B 120.7(8) . . ?
C21B C20B C25B 120.0 . . ?
C20B C21B C22B 120.0 . . ?
C23B C22B C21B 120.0 . . ?
C22B C23B C24B 120.0 . . ?
C23B C24B C25B 120.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mw400
_database_code_depnum_ccdc_archive 'CCDC 2024270'
loop_
_audit_author_name
_audit_author_address
'Duane Hean'
;University of British Columbia
Canada
;
_audit_update_record             
;
2020-08-19 deposited with the CCDC.	2021-07-28 downloaded from the CCDC.
;
_audit_creation_date             2020-08-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H21 N2 O2 S, B F4'
_chemical_formula_sum            'C21 H21 B F4 N2 O2 S'
_chemical_formula_weight         452.27
_chemical_melting_point          ?
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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   13.094(2)
_cell_length_b                   8.1898(14)
_cell_length_c                   18.731(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.965(4)
_cell_angle_gamma                90
_cell_volume                     1984.1(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9821
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      30.514
_cell_measurement_theta_min      2.201
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.925
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7150
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0775 before and 0.0369 after correction. The Ratio of minimum to maximum transmission is 0.9583. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.354
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.112
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0125
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            47914
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.534
_diffrn_reflns_theta_min         1.574
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5564
_reflns_number_total             6051
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         6051
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0323
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0476P)²+0.9114P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0868
_refine_ls_wR_factor_ref         0.0891
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C17(H17),
 C18(H18), C19(H19), C20(H20), C21(H21)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
C1 C 0.11264(7) 0.41148(11) 0.45864(5) 0.01276(15) Uani 1 1 d . . . . .
C2 C 0.06845(7) 0.30701(11) 0.50560(5) 0.01679(17) Uani 1 1 d . . . . .
H2 H 0.092013 0.311698 0.556159 0.020 Uiso 1 1 calc R . . . .
C3 C -0.00890(8) 0.19782(12) 0.47862(6) 0.01995(19) Uani 1 1 d . . . . .
H3 H -0.039343 0.132637 0.511613 0.024 Uiso 1 1 calc R . . . .
C4 C -0.04360(7) 0.18027(12) 0.40481(6) 0.02047(19) Uani 1 1 d . . . . .
H4 H -0.093693 0.100005 0.387337 0.025 Uiso 1 1 calc R . . . .
C5 C -0.00305(7) 0.28304(12) 0.35767(5) 0.01724(17) Uani 1 1 d . . . . .
H5 H -0.025664 0.274665 0.307088 0.021 Uiso 1 1 calc R . . . .
C6 C 0.07146(7) 0.39946(11) 0.38475(5) 0.01322(15) Uani 1 1 d . . . . .
C7 C 0.22725(7) 0.59491(11) 0.36314(5) 0.01363(16) Uani 1 1 d . . . . .
C8 C 0.29311(8) 0.65466(12) 0.31687(5) 0.01832(18) Uani 1 1 d . . . . .
H8 H 0.272453 0.650795 0.265980 0.022 Uiso 1 1 calc R . . . .
C9 C 0.38827(8) 0.71925(13) 0.34566(6) 0.0223(2) Uani 1 1 d . . . . .
H9 H 0.434084 0.759221 0.315066 0.027 Uiso 1 1 calc R . . . .
C10 C 0.41535(8) 0.72430(13) 0.42058(6) 0.0223(2) Uani 1 1 d . . . . .
H10 H 0.479196 0.773021 0.440758 0.027 Uiso 1 1 calc R . . . .
C11 C 0.35216(7) 0.66052(12) 0.46673(5) 0.01830(18) Uani 1 1 d . . . . .
H11 H 0.374039 0.663946 0.517503 0.022 Uiso 1 1 calc R . . . .
C12 C 0.25562(7) 0.59058(11) 0.43875(5) 0.01337(15) Uani 1 1 d . . . . .
C13 C 0.22341(7) 0.53489(12) 0.56297(5) 0.01572(16) Uani 1 1 d . . . . .
H13A H 0.161021 0.525259 0.586505 0.019 Uiso 1 1 calc R . . . .
H13B H 0.252901 0.645050 0.573856 0.019 Uiso 1 1 calc R . . . .
C14 C 0.30275(8) 0.40697(13) 0.59573(5) 0.01827(18) Uani 1 1 d . . . . .
H14A H 0.277581 0.296501 0.580403 0.022 Uiso 1 1 calc R . . . .
H14B H 0.368981 0.425413 0.577701 0.022 Uiso 1 1 calc R . . . .
C15 C 0.32049(7) 0.41713(13) 0.67852(5) 0.01870(18) Uani 1 1 d . . . . .
H15A H 0.390934 0.377532 0.697508 0.022 Uiso 1 1 calc R . . . .
H15B H 0.315599 0.532457 0.693460 0.022 Uiso 1 1 calc R . . . .
C16 C 0.24126(8) 0.31530(13) 0.71078(5) 0.01880(18) Uani 1 1 d . . . . .
H16A H 0.170564 0.345133 0.687580 0.023 Uiso 1 1 calc R . . . .
H16B H 0.252048 0.197958 0.701667 0.023 Uiso 1 1 calc R . . . .
C17 C 0.33423(8) 0.27936(14) 0.83301(6) 0.0229(2) Uani 1 1 d . . . . .
H17 H 0.380339 0.209008 0.813281 0.027 Uiso 1 1 calc R . . . .
C18 C 0.35042(10) 0.31459(18) 0.90591(6) 0.0336(3) Uani 1 1 d . . . . .
H18 H 0.407620 0.268131 0.936632 0.040 Uiso 1 1 calc R . . . .
C19 C 0.28314(11) 0.41780(17) 0.93423(6) 0.0353(3) Uani 1 1 d . . . . .
H19 H 0.294090 0.443132 0.984334 0.042 Uiso 1 1 calc R . . . .
C20 C 0.19969(11) 0.48378(14) 0.88881(6) 0.0292(2) Uani 1 1 d . . . . .
H20 H 0.152662 0.554460 0.907411 0.035 Uiso 1 1 calc R . . . .
C21 C 0.18583(8) 0.44549(12) 0.81625(6) 0.02024(19) Uani 1 1 d . . . . .
H21 H 0.128841 0.489999 0.784647 0.024 Uiso 1 1 calc R . . . .
N1 N 0.19246(6) 0.51952(10) 0.48424(4) 0.01321(14) Uani 1 1 d . . . . .
N2 N 0.25260(6) 0.34538(10) 0.78992(4) 0.01512(15) Uani 1 1 d . . . . .
O1 O 0.03693(6) 0.69036(9) 0.33297(4) 0.02011(14) Uani 1 1 d . . . . .
O2 O 0.09692(6) 0.48298(10) 0.25382(4) 0.02225(15) Uani 1 1 d . . . . .
S1 S 0.10137(2) 0.54865(3) 0.32578(2) 0.01353(6) Uani 1 1 d . . . . .
B1 B 0.38920(9) 0.93517(15) 0.64108(6) 0.0204(2) Uani 1 1 d . . . . .
F1 F 0.28172(6) 0.94363(11) 0.62813(5) 0.0442(2) Uani 1 1 d . . . . .
F2 F 0.42753(6) 0.98895(10) 0.58022(4) 0.03315(17) Uani 1 1 d . . . . .
F3 F 0.41920(7) 0.77347(9) 0.65407(5) 0.03920(19) Uani 1 1 d . . . . .
F4 F 0.42688(6) 1.03258(10) 0.70016(4) 0.03555(18) Uani 1 1 d . . . . .


_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
C1 C2 1.4139(12) . ?
C1 C6 1.4084(12) . ?
C1 N1 1.3961(11) . ?
C2 H2 0.9500 . ?
C2 C3 1.3860(14) . ?
C3 H3 0.9500 . ?
C3 C4 1.3939(15) . ?
C4 H4 0.9500 . ?
C4 C5 1.3842(14) . ?
C5 H5 0.9500 . ?
C5 C6 1.4014(13) . ?
C6 S1 1.7324(9) . ?
C7 C8 1.4026(12) . ?
C7 C12 1.4075(12) . ?
C7 S1 1.7293(9) . ?
C8 H8 0.9500 . ?
C8 C9 1.3834(14) . ?
C9 H9 0.9500 . ?
C9 C10 1.3935(16) . ?
C10 H10 0.9500 . ?
C10 C11 1.3883(14) . ?
C11 H11 0.9500 . ?
C11 C12 1.4121(13) . ?
C12 N1 1.4028(11) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.5345(13) . ?
C13 N1 1.4726(11) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.5340(13) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.5272(14) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 N2 1.4870(12) . ?
C17 H17 0.9500 . ?
C17 C18 1.3793(16) . ?
C17 N2 1.3481(12) . ?
C18 H18 0.9500 . ?
C18 C19 1.385(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.386(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.3790(15) . ?
C21 H21 0.9500 . ?
C21 N2 1.3470(13) . ?
O1 S1 1.4534(8) . ?
O2 S1 1.4438(8) . ?
B1 F1 1.3921(13) . ?
B1 F2 1.3870(13) . ?
B1 F3 1.3919(14) . ?
B1 F4 1.3908(13) . ?

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
C6 C1 C2 115.97(8) . . ?
N1 C1 C2 121.80(8) . . ?
N1 C1 C6 122.23(8) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.68(9) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 118.8 . . ?
C2 C3 C4 122.33(9) . . ?
C4 C3 H3 118.8 . . ?
C3 C4 H4 120.9 . . ?
C5 C4 C3 118.16(9) . . ?
C5 C4 H4 120.9 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.83(9) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 S1 119.17(7) . . ?
C5 C6 C1 122.79(8) . . ?
C5 C6 S1 117.57(7) . . ?
C8 C7 C12 122.64(8) . . ?
C8 C7 S1 117.73(7) . . ?
C12 C7 S1 119.16(7) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 C7 119.72(9) . . ?
C9 C8 H8 120.1 . . ?
C8 C9 H9 120.8 . . ?
C8 C9 C10 118.44(9) . . ?
C10 C9 H9 120.8 . . ?
C9 C10 H10 118.9 . . ?
C11 C10 C9 122.21(9) . . ?
C11 C10 H10 118.9 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.50(9) . . ?
C12 C11 H11 119.8 . . ?
C7 C12 C11 116.34(8) . . ?
N1 C12 C7 122.24(8) . . ?
N1 C12 C11 121.42(8) . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
N1 C13 H13A 108.8 . . ?
N1 C13 H13B 108.8 . . ?
N1 C13 C14 113.93(7) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C15 C14 C13 110.71(8) . . ?
C15 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
C14 C15 H15A 109.3 . . ?
C14 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
C16 C15 C14 111.42(8) . . ?
C16 C15 H15A 109.3 . . ?
C16 C15 H15B 109.3 . . ?
C15 C16 H16A 109.7 . . ?
C15 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
N2 C16 C15 109.60(8) . . ?
N2 C16 H16A 109.7 . . ?
N2 C16 H16B 109.7 . . ?
C18 C17 H17 120.2 . . ?
N2 C17 H17 120.2 . . ?
N2 C17 C18 119.61(11) . . ?
C17 C18 H18 120.1 . . ?
C17 C18 C19 119.87(11) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 120.3 . . ?
C18 C19 C20 119.39(10) . . ?
C20 C19 H19 120.3 . . ?
C19 C20 H20 120.4 . . ?
C21 C20 C19 119.11(11) . . ?
C21 C20 H20 120.4 . . ?
C20 C21 H21 119.8 . . ?
N2 C21 C20 120.41(10) . . ?
N2 C21 H21 119.8 . . ?
C1 N1 C12 122.34(8) . . ?
C1 N1 C13 118.20(7) . . ?
C12 N1 C13 118.46(8) . . ?
C17 N2 C16 118.49(9) . . ?
C21 N2 C16 119.75(8) . . ?
C21 N2 C17 121.61(9) . . ?
C7 S1 C6 101.09(4) . . ?
O1 S1 C6 108.17(4) . . ?
O1 S1 C7 108.54(5) . . ?
O2 S1 C6 110.62(5) . . ?
O2 S1 C7 110.90(5) . . ?
O2 S1 O1 116.39(5) . . ?
F2 B1 F1 109.05(10) . . ?
F2 B1 F3 108.50(10) . . ?
F2 B1 F4 110.05(9) . . ?
F3 B1 F1 109.14(9) . . ?
F4 B1 F1 109.50(10) . . ?
F4 B1 F3 110.56(10) . . ?

_olex2_diffrn_ambient_temperature_device 100.15
_olex2_submission_special_instructions 'No special instructions were received'
