# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

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

data_cu_garg2304_a
_database_code_depnum_ccdc_archive 'CCDC 2271421'
loop_
_audit_author_name
_audit_author_address
'Saeed I. Khan'
;UCLA
United States of America
;
_audit_update_record             
;
2023-06-21 deposited with the CCDC.	2024-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H23 Br N2 O2 S'
_chemical_formula_sum            'C22 H23 Br N2 O2 S'
_chemical_formula_weight         459.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.5459(2)
_cell_length_b                   19.1854(5)
_cell_length_c                   11.5679(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.0090(10)
_cell_angle_gamma                90
_cell_volume                     2115.65(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8933
_cell_measurement_theta_min      3.83
_cell_measurement_theta_max      68.92

_exptl_crystal_description       irregular
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .18
_exptl_crystal_size_mid          .04
_exptl_crystal_size_min          .04
_exptl_absorpt_coefficient_mu    3.728
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.64
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_process_details   'SADABS V2014/2 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I\mS micro--focus source'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            26366
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.826
_diffrn_reflns_theta_max         69.613
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             7768
_reflns_number_gt                6827
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.916
_reflns_Friedel_fraction_max     0.962
_reflns_Friedel_fraction_full    0.984

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0315P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2977 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.009(8)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         7768
_refine_ls_number_parameters     513
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0712
_refine_ls_wR_factor_gt          0.0700
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.07022(7) 0.17258(3) 0.34669(5) 0.03784(17) Uani 1 1 d . . . . .
S1 S 0.12928(13) 0.48487(6) 0.45795(10) 0.0215(3) Uani 1 1 d . . . . .
O1 O 0.0071(4) 0.52754(17) 0.4600(3) 0.0290(8) Uani 1 1 d . . . . .
O2 O 0.2382(4) 0.49999(17) 0.3818(3) 0.0276(8) Uani 1 1 d . . . . .
N1 N 0.2086(5) 0.4886(2) 0.5870(3) 0.0236(9) Uani 1 1 d . . . . .
H1N H 0.303(6) 0.479(3) 0.592(5) 0.028 Uiso 1 1 d . U . . .
N2 N 0.1269(5) 0.4728(2) 0.6799(3) 0.0244(9) Uani 1 1 d . . . . .
C1 C -0.0120(6) 0.2655(2) 0.3795(4) 0.0241(11) Uani 1 1 d . . . . .
C2 C -0.1099(6) 0.3132(2) 0.4133(4) 0.0243(11) Uani 1 1 d . . . . .
H2 H -0.2054 0.3002 0.4186 0.029 Uiso 1 1 calc R U . . .
C3 C -0.0658(5) 0.3806(2) 0.4394(4) 0.0221(11) Uani 1 1 d . . . . .
H3 H -0.1312 0.4144 0.4631 0.027 Uiso 1 1 calc R U . . .
C4 C 0.0738(5) 0.3986(2) 0.4308(4) 0.0192(10) Uani 1 1 d . . . . .
C5 C 0.1712(6) 0.3500(2) 0.3952(5) 0.0271(12) Uani 1 1 d . . . . .
H5 H 0.2665 0.3629 0.3881 0.033 Uiso 1 1 calc R U . . .
C6 C 0.1269(6) 0.2826(3) 0.3703(5) 0.0281(12) Uani 1 1 d . . . . .
H6 H 0.1919 0.2485 0.3470 0.034 Uiso 1 1 calc R U . . .
C7 C 0.1921(5) 0.4741(2) 0.7797(4) 0.0205(11) Uani 1 1 d . . . . .
C8 C 0.1158(6) 0.4607(2) 0.8851(4) 0.0237(11) Uani 1 1 d . . . . .
C9 C -0.0258(6) 0.4464(3) 0.8962(5) 0.0320(13) Uani 1 1 d . . . . .
H9 H -0.0881 0.4424 0.8297 0.038 Uiso 1 1 calc R U . . .
C10 C -0.0739(7) 0.4382(3) 1.0064(5) 0.0387(14) Uani 1 1 d . . . . .
H10 H -0.1701 0.4283 1.0159 0.046 Uiso 1 1 calc R U . . .
C11 C 0.0191(7) 0.4445(3) 1.1039(5) 0.0376(14) Uani 1 1 d . . . . .
H11 H -0.0155 0.4394 1.1790 0.045 Uiso 1 1 calc R U . . .
C12 C 0.1594(6) 0.4578(3) 1.0928(4) 0.0302(13) Uani 1 1 d . . . . .
H12 H 0.2217 0.4613 1.1593 0.036 Uiso 1 1 calc R U . . .
C13 C 0.2088(6) 0.4661(2) 0.9821(4) 0.0245(12) Uani 1 1 d . . . . .
C14 C 0.3565(5) 0.4817(3) 0.9481(4) 0.0239(11) Uani 1 1 d . . . . .
H14A H 0.4199 0.4423 0.9688 0.029 Uiso 1 1 calc R U . . .
H14B H 0.3930 0.5242 0.9877 0.029 Uiso 1 1 calc R U . . .
C15 C 0.3448(5) 0.4927(2) 0.8137(4) 0.0201(10) Uani 1 1 d . . . . .
C16 C 0.4468(6) 0.4453(3) 0.7533(4) 0.0242(12) Uani 1 1 d . . . . .
C17 C 0.4233(7) 0.3691(3) 0.7661(6) 0.0452(16) Uani 1 1 d . . . . .
H17A H 0.3229 0.3591 0.7475 0.054 Uiso 1 1 calc R U . . .
H17B H 0.4440 0.3561 0.8480 0.054 Uiso 1 1 calc R U . . .
C18 C 0.5093(10) 0.3241(4) 0.6917(9) 0.087(3) Uani 1 1 d . . . . .
H18A H 0.5181 0.2773 0.7275 0.104 Uiso 1 1 calc R U . . .
H18B H 0.4590 0.3186 0.6152 0.104 Uiso 1 1 calc R U . . .
C19 C 0.6480(9) 0.3508(4) 0.6747(9) 0.087(3) Uani 1 1 d . . . . .
H19A H 0.6925 0.3209 0.6173 0.105 Uiso 1 1 calc R U . . .
H19B H 0.7044 0.3467 0.7486 0.105 Uiso 1 1 calc R U . . .
C20 C 0.6545(7) 0.4252(4) 0.6341(6) 0.0492(17) Uani 1 1 d . . . . .
H20A H 0.7501 0.4437 0.6514 0.059 Uiso 1 1 calc R U . . .
H20B H 0.6355 0.4267 0.5492 0.059 Uiso 1 1 calc R U . . .
C21 C 0.5504(6) 0.4703(3) 0.6914(5) 0.0369(14) Uani 1 1 d . . . . .
H21 H 0.5583 0.5194 0.6835 0.044 Uiso 1 1 calc R U . . .
C22 C 0.3650(6) 0.5705(2) 0.7891(4) 0.0282(12) Uani 1 1 d . . . . .
H22A H 0.4614 0.5841 0.8123 0.042 Uiso 1 1 calc R U . . .
H22B H 0.2992 0.5978 0.8331 0.042 Uiso 1 1 calc R U . . .
H22C H 0.3473 0.5794 0.7062 0.042 Uiso 1 1 calc R U . . .
Br1A Br 0.50241(5) 0.72824(2) 0.65326(4) 0.02475(13) Uani 1 1 d . . . . .
S1A S 0.62134(13) 0.51558(6) 0.24351(10) 0.0196(3) Uani 1 1 d . . . . .
O1A O 0.4908(4) 0.48475(16) 0.2049(3) 0.0236(8) Uani 1 1 d . . . . .
O2A O 0.7402(4) 0.47336(16) 0.2767(3) 0.0238(8) Uani 1 1 d . . . . .
N1A N 0.6756(5) 0.5640(2) 0.1364(3) 0.0219(9) Uani 1 1 d . . . . .
H1AN H 0.766(6) 0.580(3) 0.155(4) 0.026 Uiso 1 1 d . U . . .
N2A N 0.5760(5) 0.61353(19) 0.0977(3) 0.0216(9) Uani 1 1 d . . . . .
C1A C 0.5384(5) 0.6650(2) 0.5326(4) 0.0200(10) Uani 1 1 d . . . . .
C2A C 0.4346(5) 0.6545(2) 0.4449(4) 0.0241(11) Uani 1 1 d . . . . .
H2A H 0.3477 0.6786 0.4454 0.029 Uiso 1 1 calc R U . . .
C3A C 0.4615(5) 0.6080(2) 0.3571(4) 0.0222(11) Uani 1 1 d . . . . .
H3A H 0.3923 0.6000 0.2965 0.027 Uiso 1 1 calc R U . . .
C4A C 0.5884(5) 0.5733(2) 0.3572(4) 0.0180(10) Uani 1 1 d . . . . .
C5A C 0.6918(5) 0.5834(2) 0.4451(4) 0.0224(11) Uani 1 1 d . . . . .
H5A H 0.7784 0.5590 0.4444 0.027 Uiso 1 1 calc R U . . .
C6A C 0.6660(5) 0.6300(2) 0.5344(4) 0.0237(11) Uani 1 1 d . . . . .
H6A H 0.7347 0.6376 0.5954 0.028 Uiso 1 1 calc R U . . .
C7A C 0.6203(5) 0.6653(3) 0.0393(4) 0.0232(11) Uani 1 1 d . . . . .
C8A C 0.5230(6) 0.7176(2) -0.0084(4) 0.0214(11) Uani 1 1 d . . . . .
C9A C 0.3761(6) 0.7187(3) -0.0060(4) 0.0298(12) Uani 1 1 d . . . . .
H9A H 0.3270 0.6830 0.0319 0.036 Uiso 1 1 calc R U . . .
C10A C 0.3048(7) 0.7735(3) -0.0608(5) 0.0338(13) Uani 1 1 d . . . . .
H10A H 0.2053 0.7754 -0.0613 0.041 Uiso 1 1 calc R U . . .
C11A C 0.3786(7) 0.8260(3) -0.1151(5) 0.0338(14) Uani 1 1 d . . . . .
H11A H 0.3282 0.8629 -0.1529 0.041 Uiso 1 1 calc R U . . .
C12A C 0.5231(6) 0.8254(2) -0.1150(4) 0.0287(13) Uani 1 1 d . . . . .
H12A H 0.5721 0.8619 -0.1508 0.034 Uiso 1 1 calc R U . . .
C13A C 0.5958(6) 0.7701(2) -0.0614(4) 0.0242(12) Uani 1 1 d . . . . .
C14A C 0.7512(6) 0.7571(3) -0.0514(5) 0.0297(13) Uani 1 1 d . . . . .
H14C H 0.7987 0.7923 -0.0005 0.036 Uiso 1 1 calc R U . . .
H14D H 0.7914 0.7591 -0.1285 0.036 Uiso 1 1 calc R U . . .
C15A C 0.7690(6) 0.6823(3) 0.0020(4) 0.0253(12) Uani 1 1 d . . . . .
C16A C 0.8744(6) 0.6844(3) 0.1061(5) 0.0281(12) Uani 1 1 d . . . . .
C17A C 0.9957(7) 0.6503(4) 0.1119(6) 0.0513(18) Uani 1 1 d . . . . .
H17C H 1.0188 0.6217 0.0486 0.062 Uiso 1 1 calc R U . . .
C18A C 1.1001(7) 0.6556(5) 0.2174(7) 0.071(3) Uani 1 1 d . . . . .
H18C H 1.1305 0.6081 0.2407 0.085 Uiso 1 1 calc R U . . .
H18D H 1.1841 0.6816 0.1949 0.085 Uiso 1 1 calc R U . . .
C19A C 1.0404(10) 0.6910(4) 0.3183(7) 0.076(3) Uani 1 1 d . . . . .
H19C H 0.9928 0.6551 0.3637 0.091 Uiso 1 1 calc R U . . .
H19D H 1.1197 0.7091 0.3681 0.091 Uiso 1 1 calc R U . . .
C20A C 0.9434(9) 0.7471(6) 0.2963(7) 0.084(3) Uani 1 1 d . . . . .
H20C H 0.9946 0.7884 0.2694 0.101 Uiso 1 1 calc R U . . .
H20D H 0.8995 0.7598 0.3691 0.101 Uiso 1 1 calc R U . . .
C21A C 0.8319(6) 0.7274(3) 0.2071(5) 0.0390(13) Uani 1 1 d . . . . .
H21A H 0.7883 0.7709 0.1763 0.047 Uiso 1 1 calc R U . . .
H21B H 0.7584 0.7015 0.2464 0.047 Uiso 1 1 calc R U . . .
C22A C 0.8038(7) 0.6312(3) -0.0932(5) 0.0367(14) Uani 1 1 d . . . . .
H22D H 0.8962 0.6423 -0.1214 0.055 Uiso 1 1 calc R U . . .
H22E H 0.7327 0.6346 -0.1572 0.055 Uiso 1 1 calc R U . . .
H22F H 0.8048 0.5836 -0.0621 0.055 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.899(5) . ?
S1 O1 1.427(4) . ?
S1 O2 1.427(4) . ?
S1 N1 1.640(4) . ?
S1 C4 1.762(5) . ?
N1 N2 1.394(6) . ?
N1 H1N 0.91(6) . ?
N2 C7 1.283(6) . ?
C1 C2 1.379(7) . ?
C1 C6 1.376(7) . ?
C2 C3 1.389(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.385(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(7) . ?
C5 C6 1.386(7) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.475(7) . ?
C7 C15 1.532(7) . ?
C8 C9 1.392(8) . ?
C8 C13 1.398(7) . ?
C9 C10 1.386(8) . ?
C9 H9 0.9500 . ?
C10 C11 1.404(8) . ?
C10 H10 0.9500 . ?
C11 C12 1.377(8) . ?
C11 H11 0.9500 . ?
C12 C13 1.396(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.514(7) . ?
C14 C15 1.567(6) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.529(7) . ?
C15 C22 1.535(6) . ?
C16 C21 1.339(8) . ?
C16 C17 1.488(8) . ?
C17 C18 1.494(9) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.443(12) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.504(10) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.499(8) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
Br1A C1A 1.894(4) . ?
S1A O1A 1.429(3) . ?
S1A O2A 1.430(3) . ?
S1A N1A 1.654(4) . ?
S1A C4A 1.760(5) . ?
N1A N2A 1.401(6) . ?
N1A H1AN 0.93(6) . ?
N2A C7A 1.285(6) . ?
C1A C6A 1.390(7) . ?
C1A C2A 1.395(7) . ?
C2A C3A 1.385(7) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.383(7) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.393(7) . ?
C5A C6A 1.397(7) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C7A C8A 1.456(7) . ?
C7A C15A 1.541(7) . ?
C8A C13A 1.386(7) . ?
C8A C9A 1.404(7) . ?
C9A C10A 1.387(7) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.397(8) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.379(8) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.394(7) . ?
C12A H12A 0.9500 . ?
C13A C14A 1.503(8) . ?
C14A C15A 1.568(7) . ?
C14A H14C 0.9900 . ?
C14A H14D 0.9900 . ?
C15A C22A 1.525(7) . ?
C15A C16A 1.528(7) . ?
C16A C17A 1.329(8) . ?
C16A C21A 1.504(8) . ?
C17A C18A 1.538(10) . ?
C17A H17C 0.9500 . ?
C18A C19A 1.489(11) . ?
C18A H18C 0.9900 . ?
C18A H18D 0.9900 . ?
C19A C20A 1.435(11) . ?
C19A H19C 0.9900 . ?
C19A H19D 0.9900 . ?
C20A C21A 1.491(9) . ?
C20A H20C 0.9900 . ?
C20A H20D 0.9900 . ?
C21A H21A 0.9900 . ?
C21A H21B 0.9900 . ?
C22A H22D 0.9800 . ?
C22A H22E 0.9800 . ?
C22A H22F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 121.1(2) . . ?
O1 S1 N1 107.4(2) . . ?
O2 S1 N1 103.7(2) . . ?
O1 S1 C4 107.7(2) . . ?
O2 S1 C4 107.6(2) . . ?
N1 S1 C4 108.9(2) . . ?
N2 N1 S1 116.2(3) . . ?
N2 N1 H1N 119(3) . . ?
S1 N1 H1N 117(3) . . ?
C7 N2 N1 115.1(4) . . ?
C2 C1 C6 122.3(5) . . ?
C2 C1 Br1 119.0(4) . . ?
C6 C1 Br1 118.8(4) . . ?
C1 C2 C3 118.5(5) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 119.9(5) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 121.0(5) . . ?
C3 C4 S1 120.1(4) . . ?
C5 C4 S1 118.8(4) . . ?
C6 C5 C4 118.9(5) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C1 C6 C5 119.4(5) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
N2 C7 C8 120.2(5) . . ?
N2 C7 C15 130.3(4) . . ?
C8 C7 C15 109.4(4) . . ?
C9 C8 C13 121.3(5) . . ?
C9 C8 C7 129.4(5) . . ?
C13 C8 C7 109.3(5) . . ?
C10 C9 C8 118.5(5) . . ?
C10 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
C9 C10 C11 120.2(6) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 121.2(5) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 119.0(5) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C12 C13 C8 119.8(5) . . ?
C12 C13 C14 128.7(5) . . ?
C8 C13 C14 111.5(4) . . ?
C13 C14 C15 105.4(4) . . ?
C13 C14 H14A 110.7 . . ?
C15 C14 H14A 110.7 . . ?
C13 C14 H14B 110.7 . . ?
C15 C14 H14B 110.7 . . ?
H14A C14 H14B 108.8 . . ?
C16 C15 C7 111.4(4) . . ?
C16 C15 C22 113.9(4) . . ?
C7 C15 C22 107.8(4) . . ?
C16 C15 C14 111.1(4) . . ?
C7 C15 C14 104.0(4) . . ?
C22 C15 C14 108.2(4) . . ?
C21 C16 C17 121.7(5) . . ?
C21 C16 C15 122.5(5) . . ?
C17 C16 C15 115.8(5) . . ?
C16 C17 C18 114.8(6) . . ?
C16 C17 H17A 108.6 . . ?
C18 C17 H17A 108.6 . . ?
C16 C17 H17B 108.6 . . ?
C18 C17 H17B 108.6 . . ?
H17A C17 H17B 107.5 . . ?
C19 C18 C17 114.1(7) . . ?
C19 C18 H18A 108.7 . . ?
C17 C18 H18A 108.7 . . ?
C19 C18 H18B 108.7 . . ?
C17 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C18 C19 C20 115.7(7) . . ?
C18 C19 H19A 108.4 . . ?
C20 C19 H19A 108.4 . . ?
C18 C19 H19B 108.4 . . ?
C20 C19 H19B 108.4 . . ?
H19A C19 H19B 107.4 . . ?
C21 C20 C19 111.7(6) . . ?
C21 C20 H20A 109.3 . . ?
C19 C20 H20A 109.3 . . ?
C21 C20 H20B 109.3 . . ?
C19 C20 H20B 109.3 . . ?
H20A C20 H20B 107.9 . . ?
C16 C21 C20 123.7(5) . . ?
C16 C21 H21 118.1 . . ?
C20 C21 H21 118.1 . . ?
C15 C22 H22A 109.5 . . ?
C15 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C15 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O1A S1A O2A 121.1(2) . . ?
O1A S1A N1A 107.5(2) . . ?
O2A S1A N1A 104.1(2) . . ?
O1A S1A C4A 107.9(2) . . ?
O2A S1A C4A 109.0(2) . . ?
N1A S1A C4A 106.4(2) . . ?
N2A N1A S1A 112.7(3) . . ?
N2A N1A H1AN 117(3) . . ?
S1A N1A H1AN 110(3) . . ?
C7A N2A N1A 117.1(4) . . ?
C6A C1A C2A 121.9(4) . . ?
C6A C1A Br1A 119.5(3) . . ?
C2A C1A Br1A 118.6(4) . . ?
C3A C2A C1A 118.3(5) . . ?
C3A C2A H2A 120.9 . . ?
C1A C2A H2A 120.9 . . ?
C4A C3A C2A 120.4(4) . . ?
C4A C3A H3A 119.8 . . ?
C2A C3A H3A 119.8 . . ?
C3A C4A C5A 121.4(4) . . ?
C3A C4A S1A 119.6(4) . . ?
C5A C4A S1A 119.1(4) . . ?
C4A C5A C6A 118.8(5) . . ?
C4A C5A H5A 120.6 . . ?
C6A C5A H5A 120.6 . . ?
C1A C6A C5A 119.2(4) . . ?
C1A C6A H6A 120.4 . . ?
C5A C6A H6A 120.4 . . ?
N2A C7A C8A 120.7(5) . . ?
N2A C7A C15A 130.1(5) . . ?
C8A C7A C15A 109.1(4) . . ?
C13A C8A C9A 121.5(5) . . ?
C13A C8A C7A 110.1(5) . . ?
C9A C8A C7A 128.4(5) . . ?
C10A C9A C8A 118.0(5) . . ?
C10A C9A H9A 121.0 . . ?
C8A C9A H9A 121.0 . . ?
C9A C10A C11A 120.3(6) . . ?
C9A C10A H10A 119.8 . . ?
C11A C10A H10A 119.8 . . ?
C12A C11A C10A 121.4(5) . . ?
C12A C11A H11A 119.3 . . ?
C10A C11A H11A 119.3 . . ?
C11A C12A C13A 118.8(5) . . ?
C11A C12A H12A 120.6 . . ?
C13A C12A H12A 120.6 . . ?
C8A C13A C12A 120.0(5) . . ?
C8A C13A C14A 111.1(4) . . ?
C12A C13A C14A 128.9(5) . . ?
C13A C14A C15A 105.6(4) . . ?
C13A C14A H14C 110.6 . . ?
C15A C14A H14C 110.6 . . ?
C13A C14A H14D 110.6 . . ?
C15A C14A H14D 110.6 . . ?
H14C C14A H14D 108.7 . . ?
C22A C15A C16A 115.2(5) . . ?
C22A C15A C7A 107.7(4) . . ?
C16A C15A C7A 111.3(4) . . ?
C22A C15A C14A 109.1(4) . . ?
C16A C15A C14A 109.9(4) . . ?
C7A C15A C14A 102.8(4) . . ?
C17A C16A C21A 120.1(5) . . ?
C17A C16A C15A 124.2(5) . . ?
C21A C16A C15A 115.7(5) . . ?
C16A C17A C18A 122.3(7) . . ?
C16A C17A H17C 118.9 . . ?
C18A C17A H17C 118.9 . . ?
C19A C18A C17A 113.2(6) . . ?
C19A C18A H18C 108.9 . . ?
C17A C18A H18C 108.9 . . ?
C19A C18A H18D 108.9 . . ?
C17A C18A H18D 108.9 . . ?
H18C C18A H18D 107.8 . . ?
C20A C19A C18A 118.2(7) . . ?
C20A C19A H19C 107.7 . . ?
C18A C19A H19C 107.7 . . ?
C20A C19A H19D 107.7 . . ?
C18A C19A H19D 107.7 . . ?
H19C C19A H19D 107.1 . . ?
C19A C20A C21A 111.3(8) . . ?
C19A C20A H20C 109.4 . . ?
C21A C20A H20C 109.4 . . ?
C19A C20A H20D 109.4 . . ?
C21A C20A H20D 109.4 . . ?
H20C C20A H20D 108.0 . . ?
C20A C21A C16A 117.7(6) . . ?
C20A C21A H21A 107.9 . . ?
C16A C21A H21A 107.9 . . ?
C20A C21A H21B 107.9 . . ?
C16A C21A H21B 107.9 . . ?
H21A C21A H21B 107.2 . . ?
C15A C22A H22D 109.5 . . ?
C15A C22A H22E 109.5 . . ?
H22D C22A H22E 109.5 . . ?
C15A C22A H22F 109.5 . . ?
H22D C22A H22F 109.5 . . ?
H22E C22A H22F 109.5 . . ?

_refine_diff_density_max         0.796
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.063

_shelxl_version_number           2014/6


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
