# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

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

data_23008
_database_code_depnum_ccdc_archive 'CCDC 2285842'
loop_
_audit_author_name
_audit_author_address
'Douglas R. Powell'
;University of Oklahoma
United States of America
;
_audit_update_record             
;
2023-07-31 deposited with the CCDC.	2023-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
#_shelx_SHELXL_version_number      '2018/3' 
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H24 Br N O4'
_chemical_formula_sum            'C21 H24 Br N O4'
_chemical_formula_weight         434.32

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'
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   8.1671(2)
_cell_length_b                   26.8544(6)
_cell_length_c                   18.1446(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.4034(8)
_cell_angle_gamma                90
_cell_volume                     3978.33(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9883
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      26.12

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_F_000             1792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.308
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.036
_exptl_absorpt_coefficient_mu    2.093
_shelx_estimated_absorpt_T_min   0.565
_shelx_estimated_absorpt_T_max   0.928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6379
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10 
;
#_exptl_absorpt_special_details    ? 
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            69735
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_av_R_equivalents  0.0610
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.246
_diffrn_reflns_theta_max         26.389
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8148
_reflns_number_gt                5833
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    'Mercury (CCDC, 2022)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2015b)'
_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)+(0.0400P)²+3.5000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     shelxt
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8148
_refine_ls_number_parameters     507
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.1041
_refine_ls_wR_factor_gt          0.0889
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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
Br1A Br -0.20072(5) 0.73275(2) 0.91177(2) 0.06589(12) Uani 1 1 d . . . . .
O1A O 0.4714(3) 0.60791(7) 0.59708(13) 0.0530(6) Uani 1 1 d . . . . .
H1A H 0.540(4) 0.5894(13) 0.610(2) 0.064 Uiso 1 1 d . U . . .
O2A O 0.1154(3) 0.64398(7) 0.61266(12) 0.0526(5) Uani 1 1 d . . . . .
O3A O 0.2479(3) 0.67554(8) 0.51713(11) 0.0535(5) Uani 1 1 d . . . . .
O4A O 0.3690(3) 0.76246(7) 0.55788(12) 0.0537(5) Uani 1 1 d . . . . .
N1A N 0.3570(3) 0.67458(8) 0.71279(12) 0.0376(5) Uani 1 1 d . . . . .
C1A C 0.2296(3) 0.68843(9) 0.75639(15) 0.0352(6) Uani 1 1 d . . . . .
C2A C 0.0965(3) 0.71787(10) 0.73104(16) 0.0395(6) Uani 1 1 d . . . . .
H2A H 0.093028 0.728979 0.681315 0.047 Uiso 1 1 calc R U . . .
C3A C -0.0279(4) 0.73077(10) 0.77677(17) 0.0430(7) Uani 1 1 d . . . . .
H3A H -0.116604 0.750367 0.758260 0.052 Uiso 1 1 calc R U . . .
C4A C -0.0254(4) 0.71553(11) 0.84940(17) 0.0461(7) Uani 1 1 d . . . . .
C5A C 0.1036(4) 0.68725(11) 0.87622(17) 0.0495(7) Uani 1 1 d . . . . .
H5A H 0.106573 0.677071 0.926382 0.059 Uiso 1 1 calc R U . . .
C6A C 0.2281(4) 0.67369(10) 0.83064(16) 0.0437(7) Uani 1 1 d . . . . .
H6A H 0.315462 0.653833 0.849889 0.052 Uiso 1 1 calc R U . . .
C7A C 0.3745(3) 0.68717(9) 0.63498(15) 0.0363(6) Uani 1 1 d . . . . .
C8A C 0.5321(3) 0.65678(10) 0.61392(16) 0.0423(7) Uani 1 1 d . . . . .
C9A C 0.6300(3) 0.65615(11) 0.68590(17) 0.0456(7) Uani 1 1 d . . . . .
H9AA H 0.709340 0.628273 0.686994 0.055 Uiso 1 1 calc R U . . .
H9AB H 0.690123 0.687831 0.693312 0.055 Uiso 1 1 calc R U . . .
C10A C 0.5025(3) 0.64937(10) 0.74392(16) 0.0424(7) Uani 1 1 d . . . . .
H10A H 0.480303 0.613614 0.752435 0.051 Uiso 1 1 calc R U . . .
H10B H 0.538358 0.664899 0.791099 0.051 Uiso 1 1 calc R U . . .
C11A C 0.6256(4) 0.67715(14) 0.5499(2) 0.0645(9) Uani 1 1 d . . . . .
H11A H 0.554801 0.677106 0.505480 0.097 Uiso 1 1 calc R U . . .
H11B H 0.721869 0.656281 0.541637 0.097 Uiso 1 1 calc R U . . .
H11C H 0.660814 0.711281 0.560918 0.097 Uiso 1 1 calc R U . . .
C12A C 0.2292(4) 0.66624(10) 0.58817(15) 0.0398(6) Uani 1 1 d . . . . .
C13A C 0.1185(5) 0.65863(15) 0.4670(2) 0.0725(11) Uani 1 1 d . . . . .
H13A H 0.018998 0.678046 0.475085 0.109 Uiso 1 1 calc R U . . .
H13B H 0.096442 0.623302 0.475917 0.109 Uiso 1 1 calc R U . . .
H13C H 0.152760 0.663113 0.415998 0.109 Uiso 1 1 calc R U . . .
C14A C 0.3958(3) 0.74302(9) 0.62713(16) 0.0391(6) Uani 1 1 d . . . . .
C15A C 0.4395(3) 0.77985(10) 0.67507(17) 0.0408(6) Uani 1 1 d . . . . .
C16A C 0.4820(4) 0.78036(10) 0.75610(18) 0.0507(8) Uani 1 1 d D . . . .
H16A H 0.552703 0.751420 0.768300 0.061 Uiso 0.820(9) 1 calc R U P A 1
H16B H 0.380459 0.777231 0.784438 0.061 Uiso 0.820(9) 1 calc R U P A 1
H16E H 0.408165 0.756738 0.780797 0.061 Uiso 0.180(9) 1 calc R U P A 2
H16F H 0.594934 0.767446 0.762767 0.061 Uiso 0.180(9) 1 calc R U P A 2
C17A C 0.5696(7) 0.82765(11) 0.7783(3) 0.0685(15) Uani 0.820(9) 1 d D U P A 1
H17A H 0.571815 0.830196 0.832704 0.082 Uiso 0.820(9) 1 calc R U P A 1
H17B H 0.684414 0.825586 0.762218 0.082 Uiso 0.820(9) 1 calc R U P A 1
C17' C 0.472(4) 0.82937(14) 0.7953(5) 0.068(2) Uani 0.180(9) 1 d D U P A 2
H17E H 0.364814 0.831775 0.818953 0.082 Uiso 0.180(9) 1 calc R U P A 2
H17F H 0.558007 0.830182 0.834905 0.082 Uiso 0.180(9) 1 calc R U P A 2
C18A C 0.4937(6) 0.87382(12) 0.7468(3) 0.0858(13) Uani 1 1 d D . . . .
H18A H 0.383467 0.877755 0.767562 0.103 Uiso 0.820(9) 1 calc R U P A 1
H18B H 0.560339 0.902734 0.763203 0.103 Uiso 0.820(9) 1 calc R U P A 1
H18C H 0.416208 0.899139 0.764843 0.103 Uiso 0.180(9) 1 calc R U P A 2
H18D H 0.604776 0.886706 0.758687 0.103 Uiso 0.180(9) 1 calc R U P A 2
C19A C 0.4771(5) 0.87526(11) 0.6649(2) 0.0660(10) Uani 1 1 d . . . . .
H19A H 0.580436 0.887731 0.644288 0.079 Uiso 1 1 calc R U . . .
H19B H 0.388692 0.898804 0.650487 0.079 Uiso 1 1 calc R U . . .
C20A C 0.4390(4) 0.82517(10) 0.6329(2) 0.0504(8) Uani 1 1 d . . . . .
C21A C 0.3976(5) 0.81248(11) 0.5636(2) 0.0629(10) Uani 1 1 d . . . . .
H21A H 0.389173 0.835249 0.523667 0.076 Uiso 1 1 calc R U . . .
Br1B Br 0.34468(5) 0.56025(2) 0.96800(2) 0.06148(12) Uani 1 1 d . . . . .
O1B O 1.0232(3) 0.54237(9) 0.60044(13) 0.0642(7) Uani 1 1 d . . . . .
H1B H 1.032(5) 0.5693(15) 0.614(2) 0.077 Uiso 1 1 d . U . . .
O2B O 0.9273(2) 0.40272(6) 0.69898(10) 0.0418(5) Uani 1 1 d . . . . .
O3B O 0.6744(3) 0.52911(8) 0.64606(12) 0.0603(6) Uani 1 1 d . . . . .
O4B O 0.7736(2) 0.45871(7) 0.60203(10) 0.0457(5) Uani 1 1 d . . . . .
N1B N 0.9059(3) 0.53376(8) 0.75829(13) 0.0401(5) Uani 1 1 d . . . . .
C1B C 0.7758(3) 0.54029(9) 0.80394(15) 0.0369(6) Uani 1 1 d . . . . .
C2B C 0.6469(3) 0.50581(9) 0.80690(15) 0.0382(6) Uani 1 1 d . . . . .
H2B H 0.646393 0.477760 0.774987 0.046 Uiso 1 1 calc R U . . .
C3B C 0.5214(3) 0.51195(9) 0.85516(15) 0.0395(6) Uani 1 1 d . . . . .
H3B H 0.435897 0.488012 0.856753 0.047 Uiso 1 1 calc R U . . .
C4B C 0.5192(4) 0.55282(10) 0.90139(15) 0.0426(7) Uani 1 1 d . . . . .
C5B C 0.6428(4) 0.58764(10) 0.89939(16) 0.0457(7) Uani 1 1 d . . . . .
H5B H 0.640914 0.615800 0.931052 0.055 Uiso 1 1 calc R U . . .
C6B C 0.7693(4) 0.58147(10) 0.85126(16) 0.0443(7) Uani 1 1 d . . . . .
H6B H 0.853969 0.605686 0.850148 0.053 Uiso 1 1 calc R U . . .
C7B C 0.9202(3) 0.49438(9) 0.70352(14) 0.0345(6) Uani 1 1 d . . . . .
C8B C 1.0767(4) 0.51038(12) 0.65900(17) 0.0491(7) Uani 1 1 d . . . . .
C9B C 1.1738(4) 0.53904(13) 0.71772(18) 0.0563(9) Uani 1 1 d . . . . .
H9BA H 1.236849 0.515921 0.750046 0.068 Uiso 1 1 calc R U . . .
H9BB H 1.250864 0.562490 0.694718 0.068 Uiso 1 1 calc R U . . .
C10B C 1.0487(4) 0.56680(11) 0.76099(18) 0.0523(8) Uani 1 1 d . . . . .
H10C H 1.087738 0.572295 0.812429 0.063 Uiso 1 1 calc R U . . .
H10D H 1.022812 0.599384 0.737989 0.063 Uiso 1 1 calc R U . . .
C11B C 1.1688(4) 0.46812(14) 0.6241(2) 0.0696(10) Uani 1 1 d . . . . .
H11D H 1.098841 0.452223 0.586268 0.104 Uiso 1 1 calc R U . . .
H11E H 1.199670 0.443596 0.661928 0.104 Uiso 1 1 calc R U . . .
H11F H 1.267740 0.481108 0.601371 0.104 Uiso 1 1 calc R U . . .
C12B C 0.9430(3) 0.44469(9) 0.74181(14) 0.0332(6) Uani 1 1 d . . . . .
C13B C 0.9908(3) 0.43176(9) 0.81158(15) 0.0350(6) Uani 1 1 d . . . . .
C14B C 1.0218(4) 0.46200(11) 0.88012(16) 0.0474(7) Uani 1 1 d . . . . .
H14A H 0.916246 0.474400 0.898511 0.057 Uiso 1 1 calc R U . . .
H14B H 1.090174 0.491200 0.868093 0.057 Uiso 1 1 calc R U . . .
C15B C 1.1080(4) 0.43155(12) 0.94026(17) 0.0560(8) Uani 1 1 d . . . . .
H15A H 1.225203 0.428187 0.928475 0.067 Uiso 1 1 calc R U . . .
H15B H 1.101373 0.449560 0.987696 0.067 Uiso 1 1 calc R U . . .
C16B C 1.0351(5) 0.38053(13) 0.94869(19) 0.0622(9) Uani 1 1 d . . . . .
H16C H 0.918001 0.383989 0.960688 0.075 Uiso 1 1 calc R U . . .
H16D H 1.090995 0.363435 0.990573 0.075 Uiso 1 1 calc R U . . .
C17B C 1.0487(4) 0.34846(11) 0.88010(17) 0.0503(8) Uani 1 1 d . . . . .
H17C H 1.162404 0.336109 0.876205 0.060 Uiso 1 1 calc R U . . .
H17D H 0.975151 0.319319 0.883749 0.060 Uiso 1 1 calc R U . . .
C18B C 1.0028(3) 0.37834(10) 0.81257(16) 0.0399(6) Uani 1 1 d . . . . .
C19B C 0.9636(4) 0.36303(10) 0.74388(18) 0.0470(7) Uani 1 1 d . . . . .
H19C H 0.961294 0.329211 0.728517 0.056 Uiso 1 1 calc R U . . .
C20B C 0.7740(3) 0.49645(9) 0.64812(15) 0.0364(6) Uani 1 1 d . . . . .
C21B C 0.6484(4) 0.45903(15) 0.54463(19) 0.0698(11) Uani 1 1 d . . . . .
H21B H 0.673919 0.433870 0.507512 0.105 Uiso 1 1 calc R U . . .
H21C H 0.644055 0.491976 0.521424 0.105 Uiso 1 1 calc R U . . .
H21D H 0.542115 0.451469 0.565917 0.105 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
Br1A C4A 1.904(3) . ?
O1A C8A 1.433(3) . ?
O1A H1A 0.78(4) . ?
O2A C12A 1.200(3) . ?
O3A C12A 1.325(3) . ?
O3A C13A 1.451(4) . ?
O4A C21A 1.367(4) . ?
O4A C14A 1.373(3) . ?
N1A C1A 1.374(4) . ?
N1A C7A 1.462(3) . ?
N1A C10A 1.468(3) . ?
C1A C6A 1.405(4) . ?
C1A C2A 1.412(4) . ?
C2A C3A 1.372(4) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.379(4) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.378(4) . ?
C5A C6A 1.375(4) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C7A C14A 1.517(3) . ?
C7A C12A 1.548(4) . ?
C7A C8A 1.579(4) . ?
C8A C11A 1.509(4) . ?
C8A C9A 1.515(4) . ?
C9A C10A 1.510(4) . ?
C9A H9AA 0.9900 . ?
C9A H9AB 0.9900 . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11C 0.9800 . ?
C13A H13A 0.9800 . ?
C13A H13B 0.9800 . ?
C13A H13C 0.9800 . ?
C14A C15A 1.359(4) . ?
C15A C20A 1.438(4) . ?
C15A C16A 1.502(4) . ?
C16A C17' 1.499(5) . ?
C16A C17A 1.507(4) . ?
C16A H16A 0.9900 . ?
C16A H16B 0.9900 . ?
C16A H16E 0.9900 . ?
C16A H16F 0.9900 . ?
C17A C18A 1.494(4) . ?
C17A H17A 0.9900 . ?
C17A H17B 0.9900 . ?
C17' C18A 1.496(5) . ?
C17' H17E 0.9900 . ?
C17' H17F 0.9900 . ?
C18A C19A 1.489(6) . ?
C18A H18A 0.9900 . ?
C18A H18B 0.9900 . ?
C18A H18C 0.9900 . ?
C18A H18D 0.9900 . ?
C19A C20A 1.495(4) . ?
C19A H19A 0.9900 . ?
C19A H19B 0.9900 . ?
C20A C21A 1.337(5) . ?
C21A H21A 0.9500 . ?
Br1B C4B 1.902(3) . ?
O1B C8B 1.427(4) . ?
O1B H1B 0.76(4) . ?
O2B C19B 1.370(3) . ?
O2B C12B 1.373(3) . ?
O3B C20B 1.196(3) . ?
O4B C20B 1.314(3) . ?
O4B C21B 1.442(3) . ?
N1B C1B 1.375(4) . ?
N1B C7B 1.458(3) . ?
N1B C10B 1.465(3) . ?
C1B C6B 1.402(4) . ?
C1B C2B 1.404(4) . ?
C2B C3B 1.374(4) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.382(4) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.377(4) . ?
C5B C6B 1.379(4) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
C7B C12B 1.514(3) . ?
C7B C20B 1.543(4) . ?
C7B C8B 1.588(4) . ?
C8B C11B 1.510(5) . ?
C8B C9B 1.521(4) . ?
C9B C10B 1.502(5) . ?
C9B H9BA 0.9900 . ?
C9B H9BB 0.9900 . ?
C10B H10C 0.9900 . ?
C10B H10D 0.9900 . ?
C11B H11D 0.9800 . ?
C11B H11E 0.9800 . ?
C11B H11F 0.9800 . ?
C12B C13B 1.361(4) . ?
C13B C18B 1.438(4) . ?
C13B C14B 1.502(4) . ?
C14B C15B 1.522(4) . ?
C14B H14A 0.9900 . ?
C14B H14B 0.9900 . ?
C15B C16B 1.503(5) . ?
C15B H15A 0.9900 . ?
C15B H15B 0.9900 . ?
C16B C17B 1.520(5) . ?
C16B H16C 0.9900 . ?
C16B H16D 0.9900 . ?
C17B C18B 1.505(4) . ?
C17B H17C 0.9900 . ?
C17B H17D 0.9900 . ?
C18B C19B 1.344(4) . ?
C19B H19C 0.9500 . ?
C21B H21B 0.9800 . ?
C21B H21C 0.9800 . ?
C21B H21D 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
C8A O1A H1A 106(3) . . ?
C12A O3A C13A 116.8(3) . . ?
C21A O4A C14A 106.3(2) . . ?
C1A N1A C7A 125.9(2) . . ?
C1A N1A C10A 121.4(2) . . ?
C7A N1A C10A 112.4(2) . . ?
N1A C1A C6A 120.0(2) . . ?
N1A C1A C2A 123.5(2) . . ?
C6A C1A C2A 116.5(3) . . ?
C3A C2A C1A 121.3(3) . . ?
C3A C2A H2A 119.3 . . ?
C1A C2A H2A 119.3 . . ?
C2A C3A C4A 120.6(3) . . ?
C2A C3A H3A 119.7 . . ?
C4A C3A H3A 119.7 . . ?
C5A C4A C3A 119.6(3) . . ?
C5A C4A Br1A 120.2(2) . . ?
C3A C4A Br1A 120.1(2) . . ?
C6A C5A C4A 120.2(3) . . ?
C6A C5A H5A 119.9 . . ?
C4A C5A H5A 119.9 . . ?
C5A C6A C1A 121.7(3) . . ?
C5A C6A H6A 119.1 . . ?
C1A C6A H6A 119.1 . . ?
N1A C7A C14A 109.5(2) . . ?
N1A C7A C12A 110.7(2) . . ?
C14A C7A C12A 113.3(2) . . ?
N1A C7A C8A 102.3(2) . . ?
C14A C7A C8A 113.1(2) . . ?
C12A C7A C8A 107.3(2) . . ?
O1A C8A C11A 110.3(3) . . ?
O1A C8A C9A 110.3(2) . . ?
C11A C8A C9A 113.7(3) . . ?
O1A C8A C7A 104.2(2) . . ?
C11A C8A C7A 115.5(2) . . ?
C9A C8A C7A 102.3(2) . . ?
C10A C9A C8A 104.1(2) . . ?
C10A C9A H9AA 110.9 . . ?
C8A C9A H9AA 110.9 . . ?
C10A C9A H9AB 110.9 . . ?
C8A C9A H9AB 110.9 . . ?
H9AA C9A H9AB 108.9 . . ?
N1A C10A C9A 104.0(2) . . ?
N1A C10A H10A 111.0 . . ?
C9A C10A H10A 111.0 . . ?
N1A C10A H10B 111.0 . . ?
C9A C10A H10B 111.0 . . ?
H10A C10A H10B 109.0 . . ?
C8A C11A H11A 109.5 . . ?
C8A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
C8A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
O2A C12A O3A 124.3(3) . . ?
O2A C12A C7A 124.6(3) . . ?
O3A C12A C7A 111.1(2) . . ?
O3A C13A H13A 109.5 . . ?
O3A C13A H13B 109.5 . . ?
H13A C13A H13B 109.5 . . ?
O3A C13A H13C 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C15A C14A O4A 110.0(2) . . ?
C15A C14A C7A 133.5(3) . . ?
O4A C14A C7A 116.5(2) . . ?
C14A C15A C20A 106.1(3) . . ?
C14A C15A C16A 133.1(2) . . ?
C20A C15A C16A 120.7(3) . . ?
C17' C16A C15A 117.3(6) . . ?
C15A C16A C17A 111.4(3) . . ?
C15A C16A H16A 109.3 . . ?
C17A C16A H16A 109.3 . . ?
C15A C16A H16B 109.3 . . ?
C17A C16A H16B 109.3 . . ?
H16A C16A H16B 108.0 . . ?
C17' C16A H16E 108.0 . . ?
C15A C16A H16E 108.0 . . ?
C17' C16A H16F 108.0 . . ?
C15A C16A H16F 108.0 . . ?
H16E C16A H16F 107.2 . . ?
C18A C17A C16A 114.0(3) . . ?
C18A C17A H17A 108.7 . . ?
C16A C17A H17A 108.7 . . ?
C18A C17A H17B 108.7 . . ?
C16A C17A H17B 108.7 . . ?
H17A C17A H17B 107.6 . . ?
C18A C17' C16A 114.4(5) . . ?
C18A C17' H17E 108.7 . . ?
C16A C17' H17E 108.7 . . ?
C18A C17' H17F 108.7 . . ?
C16A C17' H17F 108.7 . . ?
H17E C17' H17F 107.6 . . ?
C19A C18A C17A 115.5(4) . . ?
C19A C18A C17' 126.8(5) . . ?
C19A C18A H18A 108.4 . . ?
C17A C18A H18A 108.4 . . ?
C19A C18A H18B 108.4 . . ?
C17A C18A H18B 108.4 . . ?
H18A C18A H18B 107.5 . . ?
C19A C18A H18C 105.6 . . ?
C17' C18A H18C 105.6 . . ?
C19A C18A H18D 105.6 . . ?
C17' C18A H18D 105.6 . . ?
H18C C18A H18D 106.1 . . ?
C18A C19A C20A 112.2(3) . . ?
C18A C19A H19A 109.2 . . ?
C20A C19A H19A 109.2 . . ?
C18A C19A H19B 109.2 . . ?
C20A C19A H19B 109.2 . . ?
H19A C19A H19B 107.9 . . ?
C21A C20A C15A 106.4(3) . . ?
C21A C20A C19A 129.8(3) . . ?
C15A C20A C19A 123.8(3) . . ?
C20A C21A O4A 111.2(3) . . ?
C20A C21A H21A 124.4 . . ?
O4A C21A H21A 124.4 . . ?
C8B O1B H1B 108(3) . . ?
C19B O2B C12B 106.6(2) . . ?
C20B O4B C21B 116.5(2) . . ?
C1B N1B C7B 125.4(2) . . ?
C1B N1B C10B 121.9(2) . . ?
C7B N1B C10B 112.6(2) . . ?
N1B C1B C6B 120.7(3) . . ?
N1B C1B C2B 122.0(2) . . ?
C6B C1B C2B 117.2(3) . . ?
C3B C2B C1B 121.1(2) . . ?
C3B C2B H2B 119.4 . . ?
C1B C2B H2B 119.4 . . ?
C2B C3B C4B 120.2(3) . . ?
C2B C3B H3B 119.9 . . ?
C4B C3B H3B 119.9 . . ?
C5B C4B C3B 120.2(3) . . ?
C5B C4B Br1B 120.5(2) . . ?
C3B C4B Br1B 119.3(2) . . ?
C4B C5B C6B 119.7(3) . . ?
C4B C5B H5B 120.1 . . ?
C6B C5B H5B 120.1 . . ?
C5B C6B C1B 121.5(3) . . ?
C5B C6B H6B 119.2 . . ?
C1B C6B H6B 119.2 . . ?
N1B C7B C12B 109.7(2) . . ?
N1B C7B C20B 110.1(2) . . ?
C12B C7B C20B 114.5(2) . . ?
N1B C7B C8B 103.3(2) . . ?
C12B C7B C8B 112.4(2) . . ?
C20B C7B C8B 106.2(2) . . ?
O1B C8B C11B 106.7(3) . . ?
O1B C8B C9B 111.2(2) . . ?
C11B C8B C9B 114.7(3) . . ?
O1B C8B C7B 107.8(2) . . ?
C11B C8B C7B 115.2(2) . . ?
C9B C8B C7B 101.1(2) . . ?
C10B C9B C8B 105.5(3) . . ?
C10B C9B H9BA 110.6 . . ?
C8B C9B H9BA 110.6 . . ?
C10B C9B H9BB 110.6 . . ?
C8B C9B H9BB 110.6 . . ?
H9BA C9B H9BB 108.8 . . ?
N1B C10B C9B 103.5(2) . . ?
N1B C10B H10C 111.1 . . ?
C9B C10B H10C 111.1 . . ?
N1B C10B H10D 111.1 . . ?
C9B C10B H10D 111.1 . . ?
H10C C10B H10D 109.0 . . ?
C8B C11B H11D 109.5 . . ?
C8B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
C8B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
C13B C12B O2B 109.7(2) . . ?
C13B C12B C7B 132.9(2) . . ?
O2B C12B C7B 117.1(2) . . ?
C12B C13B C18B 106.5(2) . . ?
C12B C13B C14B 132.2(2) . . ?
C18B C13B C14B 121.3(2) . . ?
C13B C14B C15B 111.6(2) . . ?
C13B C14B H14A 109.3 . . ?
C15B C14B H14A 109.3 . . ?
C13B C14B H14B 109.3 . . ?
C15B C14B H14B 109.3 . . ?
H14A C14B H14B 108.0 . . ?
C16B C15B C14B 112.7(3) . . ?
C16B C15B H15A 109.1 . . ?
C14B C15B H15A 109.1 . . ?
C16B C15B H15B 109.1 . . ?
C14B C15B H15B 109.1 . . ?
H15A C15B H15B 107.8 . . ?
C15B C16B C17B 113.3(3) . . ?
C15B C16B H16C 108.9 . . ?
C17B C16B H16C 108.9 . . ?
C15B C16B H16D 108.9 . . ?
C17B C16B H16D 108.9 . . ?
H16C C16B H16D 107.7 . . ?
C18B C17B C16B 110.1(2) . . ?
C18B C17B H17C 109.6 . . ?
C16B C17B H17C 109.6 . . ?
C18B C17B H17D 109.6 . . ?
C16B C17B H17D 109.6 . . ?
H17C C17B H17D 108.2 . . ?
C19B C18B C13B 106.2(2) . . ?
C19B C18B C17B 129.9(3) . . ?
C13B C18B C17B 123.9(3) . . ?
C18B C19B O2B 110.9(2) . . ?
C18B C19B H19C 124.6 . . ?
O2B C19B H19C 124.6 . . ?
O3B C20B O4B 123.7(3) . . ?
O3B C20B C7B 124.2(3) . . ?
O4B C20B C7B 112.1(2) . . ?
O4B C21B H21B 109.5 . . ?
O4B C21B H21C 109.5 . . ?
H21B C21B H21C 109.5 . . ?
O4B C21B H21D 109.5 . . ?
H21B C21B H21D 109.5 . . ?
H21C C21B H21D 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
C7A N1A C1A C6A 180.0(2) . . . . ?
C10A N1A C1A C6A -7.1(4) . . . . ?
C7A N1A C1A C2A -0.8(4) . . . . ?
C10A N1A C1A C2A 172.2(2) . . . . ?
N1A C1A C2A C3A -179.9(2) . . . . ?
C6A C1A C2A C3A -0.7(4) . . . . ?
C1A C2A C3A C4A 0.6(4) . . . . ?
C2A C3A C4A C5A 0.2(4) . . . . ?
C2A C3A C4A Br1A -178.9(2) . . . . ?
C3A C4A C5A C6A -0.9(4) . . . . ?
Br1A C4A C5A C6A 178.3(2) . . . . ?
C4A C5A C6A C1A 0.8(4) . . . . ?
N1A C1A C6A C5A 179.3(3) . . . . ?
C2A C1A C6A C5A 0.0(4) . . . . ?
C1A N1A C7A C14A 65.3(3) . . . . ?
C10A N1A C7A C14A -108.2(2) . . . . ?
C1A N1A C7A C12A -60.3(3) . . . . ?
C10A N1A C7A C12A 126.2(2) . . . . ?
C1A N1A C7A C8A -174.5(2) . . . . ?
C10A N1A C7A C8A 12.1(3) . . . . ?
N1A C7A C8A O1A 84.0(2) . . . . ?
C14A C7A C8A O1A -158.4(2) . . . . ?
C12A C7A C8A O1A -32.7(3) . . . . ?
N1A C7A C8A C11A -154.9(3) . . . . ?
C14A C7A C8A C11A -37.3(3) . . . . ?
C12A C7A C8A C11A 88.4(3) . . . . ?
N1A C7A C8A C9A -30.9(3) . . . . ?
C14A C7A C8A C9A 86.8(3) . . . . ?
C12A C7A C8A C9A -147.5(2) . . . . ?
O1A C8A C9A C10A -71.6(3) . . . . ?
C11A C8A C9A C10A 164.0(3) . . . . ?
C7A C8A C9A C10A 38.8(3) . . . . ?
C1A N1A C10A C9A -162.1(2) . . . . ?
C7A N1A C10A C9A 11.7(3) . . . . ?
C8A C9A C10A N1A -31.7(3) . . . . ?
C13A O3A C12A O2A 1.9(4) . . . . ?
C13A O3A C12A C7A -179.0(2) . . . . ?
N1A C7A C12A O2A 2.0(4) . . . . ?
C14A C7A C12A O2A -121.5(3) . . . . ?
C8A C7A C12A O2A 113.0(3) . . . . ?
N1A C7A C12A O3A -177.2(2) . . . . ?
C14A C7A C12A O3A 59.4(3) . . . . ?
C8A C7A C12A O3A -66.2(3) . . . . ?
C21A O4A C14A C15A 0.2(3) . . . . ?
C21A O4A C14A C7A -179.0(3) . . . . ?
N1A C7A C14A C15A 18.4(4) . . . . ?
C12A C7A C14A C15A 142.5(3) . . . . ?
C8A C7A C14A C15A -95.0(4) . . . . ?
N1A C7A C14A O4A -162.7(2) . . . . ?
C12A C7A C14A O4A -38.5(3) . . . . ?
C8A C7A C14A O4A 83.9(3) . . . . ?
O4A C14A C15A C20A 0.3(3) . . . . ?
C7A C14A C15A C20A 179.3(3) . . . . ?
O4A C14A C15A C16A 179.8(3) . . . . ?
C7A C14A C15A C16A -1.2(6) . . . . ?
C14A C15A C16A C17' -161.0(12) . . . . ?
C20A C15A C16A C17' 18.4(12) . . . . ?
C14A C15A C16A C17A 162.9(4) . . . . ?
C20A C15A C16A C17A -17.6(5) . . . . ?
C15A C16A C17A C18A 45.2(6) . . . . ?
C15A C16A C17' C18A -25(2) . . . . ?
C16A C17A C18A C19A -56.9(7) . . . . ?
C16A C17' C18A C19A 18(3) . . . . ?
C17A C18A C19A C20A 35.6(5) . . . . ?
C17' C18A C19A C20A -1.5(14) . . . . ?
C14A C15A C20A C21A -0.7(4) . . . . ?
C16A C15A C20A C21A 179.7(3) . . . . ?
C14A C15A C20A C19A 178.7(3) . . . . ?
C16A C15A C20A C19A -0.9(5) . . . . ?
C18A C19A C20A C21A 171.6(4) . . . . ?
C18A C19A C20A C15A -7.6(5) . . . . ?
C15A C20A C21A O4A 0.8(4) . . . . ?
C19A C20A C21A O4A -178.5(3) . . . . ?
C14A O4A C21A C20A -0.7(4) . . . . ?
C7B N1B C1B C6B -175.6(2) . . . . ?
C10B N1B C1B C6B 5.0(4) . . . . ?
C7B N1B C1B C2B 6.2(4) . . . . ?
C10B N1B C1B C2B -173.2(3) . . . . ?
N1B C1B C2B C3B 177.2(2) . . . . ?
C6B C1B C2B C3B -1.1(4) . . . . ?
C1B C2B C3B C4B 0.7(4) . . . . ?
C2B C3B C4B C5B 0.0(4) . . . . ?
C2B C3B C4B Br1B -179.7(2) . . . . ?
C3B C4B C5B C6B -0.3(4) . . . . ?
Br1B C4B C5B C6B 179.4(2) . . . . ?
C4B C5B C6B C1B -0.1(4) . . . . ?
N1B C1B C6B C5B -177.5(3) . . . . ?
C2B C1B C6B C5B 0.8(4) . . . . ?
C1B N1B C7B C12B -69.3(3) . . . . ?
C10B N1B C7B C12B 110.2(2) . . . . ?
C1B N1B C7B C20B 57.7(3) . . . . ?
C10B N1B C7B C20B -122.9(2) . . . . ?
C1B N1B C7B C8B 170.7(2) . . . . ?
C10B N1B C7B C8B -9.8(3) . . . . ?
N1B C7B C8B O1B -88.3(3) . . . . ?
C12B C7B C8B O1B 153.5(2) . . . . ?
C20B C7B C8B O1B 27.6(3) . . . . ?
N1B C7B C8B C11B 152.7(3) . . . . ?
C12B C7B C8B C11B 34.6(4) . . . . ?
C20B C7B C8B C11B -91.4(3) . . . . ?
N1B C7B C8B C9B 28.5(3) . . . . ?
C12B C7B C8B C9B -89.7(3) . . . . ?
C20B C7B C8B C9B 144.4(2) . . . . ?
O1B C8B C9B C10B 76.7(3) . . . . ?
C11B C8B C9B C10B -162.1(3) . . . . ?
C7B C8B C9B C10B -37.5(3) . . . . ?
C1B N1B C10B C9B 166.1(2) . . . . ?
C7B N1B C10B C9B -13.4(3) . . . . ?
C8B C9B C10B N1B 32.2(3) . . . . ?
C19B O2B C12B C13B 1.1(3) . . . . ?
C19B O2B C12B C7B 176.0(2) . . . . ?
N1B C7B C12B C13B -18.6(4) . . . . ?
C20B C7B C12B C13B -143.1(3) . . . . ?
C8B C7B C12B C13B 95.7(3) . . . . ?
N1B C7B C12B O2B 167.9(2) . . . . ?
C20B C7B C12B O2B 43.5(3) . . . . ?
C8B C7B C12B O2B -77.8(3) . . . . ?
O2B C12B C13B C18B -1.1(3) . . . . ?
C7B C12B C13B C18B -174.9(3) . . . . ?
O2B C12B C13B C14B -178.3(3) . . . . ?
C7B C12B C13B C14B 7.9(5) . . . . ?
C12B C13B C14B C15B -167.9(3) . . . . ?
C18B C13B C14B C15B 15.3(4) . . . . ?
C13B C14B C15B C16B -44.7(4) . . . . ?
C14B C15B C16B C17B 62.4(4) . . . . ?
C15B C16B C17B C18B -44.7(4) . . . . ?
C12B C13B C18B C19B 0.7(3) . . . . ?
C14B C13B C18B C19B 178.3(3) . . . . ?
C12B C13B C18B C17B -178.5(3) . . . . ?
C14B C13B C18B C17B -1.0(4) . . . . ?
C16B C17B C18B C19B -163.9(3) . . . . ?
C16B C17B C18B C13B 15.2(4) . . . . ?
C13B C18B C19B O2B 0.0(3) . . . . ?
C17B C18B C19B O2B 179.1(3) . . . . ?
C12B O2B C19B C18B -0.6(3) . . . . ?
C21B O4B C20B O3B 2.7(4) . . . . ?
C21B O4B C20B C7B -175.7(3) . . . . ?
N1B C7B C20B O3B 7.7(4) . . . . ?
C12B C7B C20B O3B 132.0(3) . . . . ?
C8B C7B C20B O3B -103.4(3) . . . . ?
N1B C7B C20B O4B -173.9(2) . . . . ?
C12B C7B C20B O4B -49.6(3) . . . . ?
C8B C7B C20B O4B 75.0(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1A H1A O3B 0.78(4) 2.05(4) 2.819(3) 166(4) . yes
C11A H11A O3A 0.98 2.52 3.127(4) 119.9 . yes
C21A H21A Br1B 0.95 3.00 3.853(3) 149.9 4_575 yes
O1B H1B O2A 0.76(4) 2.12(4) 2.838(3) 157(4) 1_655 yes
C21B H21B O1A 0.98 2.48 3.268(4) 137.0 3_666 yes

_refine_diff_density_max         0.543
_refine_diff_density_min         -0.613
_refine_diff_density_rms         0.053

