# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_shi_4973_elba_auto
_database_code_depnum_ccdc_archive 'CCDC 2212999'
loop_
_audit_author_name
_audit_author_address
'Sergiu shova'
;Institute of Macromolecular Chemistry, Iasi
Romania
;
_audit_update_record             
;
2022-10-14 deposited with the CCDC.	2023-01-09 downloaded from the CCDC.
;
_audit_creation_date             2022-10-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H19 Br N2 O2 Si'
_chemical_formula_sum            'C21 H19 Br N2 O2 Si'
_chemical_formula_weight         439.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N3O2
_chemical_oxdiff_usercomment     'AZD_35 Fr13'
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'
Si Si 0.0817 0.0704 '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                   9.5866(6)
_cell_length_b                   20.1420(7)
_cell_length_c                   31.2607(17)
_cell_angle_alpha                90
_cell_angle_beta                 94.699(5)
_cell_angle_gamma                90
_cell_volume                     6015.9(5)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    3700
_cell_measurement_temperature    160.2(5)
_cell_measurement_theta_max      21.3820
_cell_measurement_theta_min      2.0210
_shelx_estimated_absorpt_T_max   0.901
_shelx_estimated_absorpt_T_min   0.676
_exptl_absorpt_coefficient_mu    2.128
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.05806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2688
_exptl_crystal_size_max          0.2
_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  0.1261
_diffrn_reflns_av_unetI/netI     0.1827
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            32300
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.022
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160.2(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1593
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -18.00   7.00   1.00   30.00    --  -15.29  21.00-140.00   25
  2  ω    -46.00  46.00   1.00   30.00    --   17.79 -21.00  52.00   92
  3  ω     29.00  73.00   1.00   30.00    --   17.79  21.00-140.00   44
  4  ω    -86.00 -40.00   1.00   30.00    --  -15.29-178.00-150.00   46
  5  ω      1.00  58.00   1.00   30.00    --   17.79  57.00 -90.00   57
  6  ω      3.00  28.00   1.00   30.00    --   17.79  77.00 -90.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0354273000
_diffrn_orient_matrix_UB_12      0.0067904000
_diffrn_orient_matrix_UB_13      0.0185674000
_diffrn_orient_matrix_UB_21      0.0623931000
_diffrn_orient_matrix_UB_22      -0.0065431000
_diffrn_orient_matrix_UB_23      0.0131220000
_diffrn_orient_matrix_UB_31      0.0190630000
_diffrn_orient_matrix_UB_32      0.0339269000
_diffrn_orient_matrix_UB_33      -0.0011948000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5592
_reflns_number_total             10608
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.966
_refine_diff_density_min         -0.908
_refine_diff_density_rms         0.113
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     742
_refine_ls_number_reflns         10608
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1662
_refine_ls_R_factor_gt           0.0808
_refine_ls_restrained_S_all      1.002
_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)+(0.0520P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1440
_refine_ls_wR_factor_ref         0.1794
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C7C) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.02
Uanis(N1C) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C3A(H3A), C5A(H5A), C6A(H6A), C17A(H17A), C19A(H19A), C20A(H20A),
 C2B(H2B), C3B(H3B), C5B(H5B), C6B(H6B), C17B(H17B), C19B(H19B), C20B(H20B),
 C2C(H2C), C3C(H3C), C5C(H5C), C6C(H6C), C17C(H17C), C19C(H19C), C20C(H20C)
3.b Idealised Me refined as rotating group:
 C10A(H10A,H10B,H10C), C11A(H11A,H11B,H11C), C12A(H12A,H12B,H12C), C16A(H16A,
 H16B,H16C), C10B(H10D,H10E,H10F), C11B(H11D,H11E,H11F), C12B(H12D,H12E,H12F),
 C16B(H16D,H16E,H16F), C10C(H10G,H10H,H10I), C11C(H11G,H11H,H11I), C12C(H12G,
 H12H,H12I), C16C(H16G,H16H,H16I)
;
_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
Br1A Br -0.28611(9) 1.00427(3) 0.49130(3) 0.0406(3) Uani 1 1 d . . . . .
Si1A Si 0.4879(2) 0.80890(9) 0.42184(7) 0.0220(5) Uani 1 1 d . . . . .
O1A O 0.1729(6) 0.8585(2) 0.36192(17) 0.0388(15) Uani 1 1 d . . . . .
O2A O 0.5481(5) 0.6633(2) 0.43874(19) 0.0419(16) Uani 1 1 d . . . . .
N1A N 0.0980(6) 0.7310(2) 0.43069(19) 0.0238(15) Uani 1 1 d . . . . .
N2A N -0.1789(7) 0.5339(3) 0.5002(3) 0.054(2) Uani 1 1 d . . . . .
C1A C 0.0374(8) 0.8836(3) 0.4203(2) 0.0236(18) Uani 1 1 d . . . . .
C2A C -0.0487(8) 0.9294(3) 0.3981(2) 0.031(2) Uani 1 1 d . . . . .
H2A H -0.041822 0.935296 0.368150 0.038 Uiso 1 1 calc R U . . .
C3A C -0.1444(8) 0.9666(3) 0.4186(2) 0.030(2) Uani 1 1 d . . . . .
H3A H -0.203109 0.997994 0.403303 0.036 Uiso 1 1 calc R U . . .
C4A C -0.1520(8) 0.9566(3) 0.4623(3) 0.0267(19) Uani 1 1 d . . . . .
C5A C -0.0628(8) 0.9132(3) 0.4856(3) 0.030(2) Uani 1 1 d . . . . .
H5A H -0.066198 0.908825 0.515754 0.036 Uiso 1 1 calc R U . . .
C6A C 0.0312(8) 0.8763(3) 0.4640(3) 0.029(2) Uani 1 1 d . . . . .
H6A H 0.091832 0.845789 0.479429 0.035 Uiso 1 1 calc R U . . .
C7A C 0.1352(8) 0.8420(3) 0.3965(3) 0.0276(19) Uani 1 1 d . . . . .
C8A C 0.1878(8) 0.7783(3) 0.4170(2) 0.0222(18) Uani 1 1 d . . . . .
C9A C 0.3252(7) 0.7567(3) 0.4254(2) 0.0208(17) Uani 1 1 d . . . . .
C10A C 0.4405(8) 0.8986(3) 0.4173(2) 0.032(2) Uani 1 1 d . . . . .
H10A H 0.392898 0.907229 0.388930 0.048 Uiso 1 1 calc R U . . .
H10B H 0.525562 0.925602 0.421186 0.048 Uiso 1 1 calc R U . . .
H10C H 0.378003 0.909988 0.439515 0.048 Uiso 1 1 calc R U . . .
C11A C 0.5835(8) 0.7878(3) 0.3747(2) 0.033(2) Uani 1 1 d . . . . .
H11A H 0.622541 0.742944 0.378178 0.050 Uiso 1 1 calc R U . . .
H11B H 0.659641 0.819681 0.372217 0.050 Uiso 1 1 calc R U . . .
H11C H 0.519167 0.789506 0.348702 0.050 Uiso 1 1 calc R U . . .
C12A C 0.6013(8) 0.8031(3) 0.4728(2) 0.038(2) Uani 1 1 d . . . . .
H12A H 0.552450 0.822391 0.496174 0.057 Uiso 1 1 calc R U . . .
H12B H 0.688461 0.827564 0.469900 0.057 Uiso 1 1 calc R U . . .
H12C H 0.622855 0.756450 0.479167 0.057 Uiso 1 1 calc R U . . .
C13A C 0.3164(8) 0.6926(3) 0.4449(2) 0.0229(18) Uani 1 1 d . . . . .
C14A C 0.1774(8) 0.6776(3) 0.4493(2) 0.0244(18) Uani 1 1 d . . . . .
C15A C 0.4394(8) 0.6500(3) 0.4545(2) 0.0243(18) Uani 1 1 d . . . . .
C16A C 0.4313(8) 0.5897(3) 0.4826(2) 0.033(2) Uani 1 1 d . . . . .
H16A H 0.376912 0.554998 0.466908 0.050 Uiso 1 1 calc R U . . .
H16B H 0.385728 0.601618 0.508496 0.050 Uiso 1 1 calc R U . . .
H16C H 0.525985 0.573328 0.490787 0.050 Uiso 1 1 calc R U . . .
C17A C 0.1033(8) 0.6242(3) 0.4664(2) 0.0275(19) Uani 1 1 d . . . . .
H17A H 0.152346 0.587289 0.479180 0.033 Uiso 1 1 calc R U . . .
C18A C -0.0421(8) 0.6264(3) 0.4641(3) 0.029(2) Uani 1 1 d . . . . .
C19A C -0.1176(8) 0.6786(3) 0.4425(2) 0.031(2) Uani 1 1 d . . . . .
H19A H -0.217048 0.677742 0.439618 0.037 Uiso 1 1 calc R U . . .
C20A C -0.0490(8) 0.7287(3) 0.4263(3) 0.030(2) Uani 1 1 d . . . . .
H20A H -0.099914 0.763460 0.411653 0.036 Uiso 1 1 calc R U . . .
C21A C -0.1182(8) 0.5750(3) 0.4841(3) 0.036(2) Uani 1 1 d . . . . .
Br1B Br 0.83626(11) 0.94012(4) 0.68833(3) 0.0541(3) Uani 1 1 d . . . . .
Si1B Si 0.0365(2) 0.76723(9) 0.59316(7) 0.0242(5) Uani 1 1 d . . . . .
O1B O 0.3306(6) 0.8302(2) 0.53636(17) 0.0359(14) Uani 1 1 d . . . . .
O2B O -0.0305(5) 0.6251(2) 0.59482(19) 0.0439(16) Uani 1 1 d . . . . .
N1B N 0.4236(6) 0.6837(2) 0.58524(18) 0.0199(14) Uani 1 1 d . . . . .
N2B N 0.7192(7) 0.4642(3) 0.6206(2) 0.0423(19) Uani 1 1 d . . . . .
C1B C 0.4894(8) 0.8366(3) 0.5986(2) 0.0237(18) Uani 1 1 d . . . . .
C2B C 0.5640(8) 0.8903(3) 0.5841(3) 0.032(2) Uani 1 1 d . . . . .
H2B H 0.544824 0.905661 0.555468 0.039 Uiso 1 1 calc R U . . .
C3B C 0.6656(8) 0.9215(3) 0.6108(3) 0.033(2) Uani 1 1 d . . . . .
H3B H 0.715755 0.958185 0.600616 0.040 Uiso 1 1 calc R U . . .
C4B C 0.6935(8) 0.8995(3) 0.6517(3) 0.032(2) Uani 1 1 d . . . . .
C5B C 0.6219(9) 0.8459(3) 0.6673(3) 0.037(2) Uani 1 1 d . . . . .
H5B H 0.641809 0.830625 0.695876 0.045 Uiso 1 1 calc R U . . .
C6B C 0.5208(9) 0.8155(4) 0.6399(3) 0.036(2) Uani 1 1 d . . . . .
H6B H 0.471414 0.778596 0.650136 0.043 Uiso 1 1 calc R U . . .
C7B C 0.3819(7) 0.8040(3) 0.5695(2) 0.0204(17) Uani 1 1 d . . . . .
C8B C 0.3292(8) 0.7360(3) 0.5806(2) 0.0217(18) Uani 1 1 d . . . . .
C9B C 0.1960(7) 0.7142(3) 0.5861(2) 0.0212(17) Uani 1 1 d . . . . .
C10B C 0.0931(8) 0.8564(3) 0.5963(3) 0.036(2) Uani 1 1 d . . . . .
H10D H 0.168891 0.861583 0.619049 0.054 Uiso 1 1 calc R U . . .
H10E H 0.013678 0.884327 0.602676 0.054 Uiso 1 1 calc R U . . .
H10F H 0.126291 0.869934 0.568762 0.054 Uiso 1 1 calc R U . . .
C11B C -0.0979(8) 0.7594(3) 0.5477(2) 0.033(2) Uani 1 1 d . . . . .
H11D H -0.056198 0.769655 0.520900 0.050 Uiso 1 1 calc R U . . .
H11E H -0.174404 0.790569 0.551604 0.050 Uiso 1 1 calc R U . . .
H11F H -0.134409 0.713989 0.546556 0.050 Uiso 1 1 calc R U . . .
C12B C -0.0337(8) 0.7495(4) 0.6458(2) 0.036(2) Uani 1 1 d . . . . .
H12D H -0.075493 0.705049 0.645175 0.053 Uiso 1 1 calc R U . . .
H12E H -0.105035 0.782511 0.651370 0.053 Uiso 1 1 calc R U . . .
H12F H 0.042650 0.751508 0.668657 0.053 Uiso 1 1 calc R U . . .
C13B C 0.2082(8) 0.6436(3) 0.5941(2) 0.0210(17) Uani 1 1 d . . . . .
C14B C 0.3492(7) 0.6261(3) 0.5943(2) 0.0172(16) Uani 1 1 d . . . . .
C15B C 0.0867(8) 0.6010(3) 0.5996(2) 0.0191(17) Uani 1 1 d . . . . .
C16B C 0.1035(8) 0.5283(3) 0.6081(3) 0.036(2) Uani 1 1 d . . . . .
H16D H 0.155077 0.521614 0.636183 0.053 Uiso 1 1 calc R U . . .
H16E H 0.155335 0.508008 0.585753 0.053 Uiso 1 1 calc R U . . .
H16F H 0.010982 0.507537 0.608090 0.053 Uiso 1 1 calc R U . . .
C17B C 0.4284(7) 0.5681(3) 0.6026(2) 0.0208(17) Uani 1 1 d . . . . .
H17B H 0.382846 0.528048 0.609375 0.025 Uiso 1 1 calc R U . . .
C18B C 0.5679(8) 0.5688(3) 0.6009(2) 0.0236(18) Uani 1 1 d . . . . .
C19B C 0.6402(8) 0.6270(3) 0.5886(2) 0.0260(18) Uani 1 1 d . . . . .
H19B H 0.738132 0.626050 0.585770 0.031 Uiso 1 1 calc R U . . .
C20B C 0.5657(8) 0.6832(3) 0.5810(2) 0.0279(19) Uani 1 1 d . . . . .
H20B H 0.611124 0.722491 0.572654 0.033 Uiso 1 1 calc R U . . .
C21B C 0.6540(8) 0.5108(3) 0.6130(3) 0.031(2) Uani 1 1 d . . . . .
Br1C Br 1.22928(10) 0.44871(4) 0.80172(3) 0.0493(3) Uani 1 1 d . . . . .
Si1C Si 0.4389(2) 0.66293(9) 0.75070(7) 0.0253(5) Uani 1 1 d . . . . .
O1C O 0.7208(6) 0.6284(2) 0.68687(16) 0.0351(14) Uani 1 1 d . . . . .
O2C O 0.3867(6) 0.8078(3) 0.77908(19) 0.0466(16) Uani 1 1 d . . . . .
N1C N 0.8313(6) 0.7440(2) 0.76312(18) 0.0185(14) Uani 1 1 d . U . . .
N2C N 1.1450(8) 0.9407(3) 0.8320(2) 0.053(2) Uani 1 1 d . . . . .
C1C C 0.8896(8) 0.5943(3) 0.7416(2) 0.0276(19) Uani 1 1 d . . . . .
C2C C 0.9118(8) 0.5881(3) 0.7860(3) 0.033(2) Uani 1 1 d . . . . .
H2C H 0.858661 0.614060 0.804202 0.040 Uiso 1 1 calc R U . . .
C3C C 1.0114(9) 0.5442(3) 0.8037(3) 0.035(2) Uani 1 1 d . . . . .
H3C H 1.026474 0.539545 0.833941 0.042 Uiso 1 1 calc R U . . .
C4C C 1.0890(8) 0.5069(3) 0.7770(3) 0.032(2) Uani 1 1 d . . . . .
C5C C 1.0705(9) 0.5132(4) 0.7334(3) 0.037(2) Uani 1 1 d . . . . .
H5C H 1.126808 0.488577 0.715440 0.045 Uiso 1 1 calc R U . . .
C6C C 0.9678(9) 0.5563(3) 0.7157(3) 0.036(2) Uani 1 1 d . . . . .
H6C H 0.951423 0.559593 0.685400 0.043 Uiso 1 1 calc R U . . .
C7C C 0.7789(8) 0.6390(3) 0.7226(2) 0.0209(17) Uani 1 1 d . U . . .
C8C C 0.7348(8) 0.6968(3) 0.7474(2) 0.0215(17) Uani 1 1 d . . . . .
C9C C 0.6022(8) 0.7155(3) 0.7577(2) 0.0202(17) Uani 1 1 d . . . . .
C10C C 0.3448(8) 0.6637(4) 0.8000(2) 0.039(2) Uani 1 1 d . . . . .
H10G H 0.412609 0.666041 0.825152 0.058 Uiso 1 1 calc R U . . .
H10H H 0.289123 0.623093 0.801301 0.058 Uiso 1 1 calc R U . . .
H10I H 0.282873 0.702453 0.799576 0.058 Uiso 1 1 calc R U . . .
C11C C 0.4893(9) 0.5745(3) 0.7419(3) 0.049(3) Uani 1 1 d . . . . .
H11G H 0.520711 0.569672 0.712995 0.074 Uiso 1 1 calc R U . . .
H11H H 0.408239 0.545735 0.744828 0.074 Uiso 1 1 calc R U . . .
H11I H 0.565285 0.561900 0.763208 0.074 Uiso 1 1 calc R U . . .
C12C C 0.3213(8) 0.6899(4) 0.7046(2) 0.039(2) Uani 1 1 d . . . . .
H12G H 0.301870 0.737426 0.707171 0.058 Uiso 1 1 calc R U . . .
H12H H 0.233391 0.664948 0.704094 0.058 Uiso 1 1 calc R U . . .
H12I H 0.365863 0.681660 0.678003 0.058 Uiso 1 1 calc R U . . .
C13C C 0.6210(8) 0.7759(3) 0.7818(2) 0.0222(18) Uani 1 1 d . . . . .
C14C C 0.7628(8) 0.7932(3) 0.7853(2) 0.0230(18) Uani 1 1 d . . . . .
C15C C 0.5044(8) 0.8153(3) 0.7965(2) 0.0255(18) Uani 1 1 d . . . . .
C16C C 0.5316(8) 0.8654(3) 0.8317(3) 0.039(2) Uani 1 1 d . . . . .
H16G H 0.576376 0.904731 0.820457 0.058 Uiso 1 1 calc R U . . .
H16H H 0.593307 0.845984 0.854958 0.058 Uiso 1 1 calc R U . . .
H16I H 0.442716 0.878254 0.842806 0.058 Uiso 1 1 calc R U . . .
C17C C 0.8462(8) 0.8460(3) 0.8035(2) 0.0265(19) Uani 1 1 d . . . . .
H17C H 0.804638 0.879770 0.819458 0.032 Uiso 1 1 calc R U . . .
C18C C 0.9853(8) 0.8483(3) 0.7981(2) 0.0275(19) Uani 1 1 d . . . . .
C19C C 1.0511(8) 0.7989(3) 0.7735(2) 0.0271(19) Uani 1 1 d . . . . .
H19C H 1.147546 0.801968 0.768774 0.032 Uiso 1 1 calc R U . . .
C20C C 0.9727(8) 0.7483(3) 0.7574(2) 0.029(2) Uani 1 1 d . . . . .
H20C H 1.015074 0.714648 0.741569 0.035 Uiso 1 1 calc R U . . .
C21C C 1.0725(8) 0.9010(4) 0.8168(3) 0.035(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
Br1A C4A 1.894(7) . ?
Si1A C9A 1.892(7) . ?
Si1A C10A 1.865(6) . ?
Si1A C11A 1.848(7) . ?
Si1A C12A 1.857(8) . ?
O1A C7A 1.215(8) . ?
O2A C15A 1.219(8) . ?
N1A C8A 1.376(8) . ?
N1A C14A 1.415(8) . ?
N1A C20A 1.405(9) . ?
N2A C21A 1.151(9) . ?
C1A C2A 1.386(9) . ?
C1A C6A 1.381(10) . ?
C1A C7A 1.500(9) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.383(10) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.387(10) . ?
C4A C5A 1.388(9) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.385(10) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.502(9) . ?
C8A C9A 1.393(9) . ?
C9A C13A 1.432(9) . ?
C10A H10A 0.9800 . ?
C10A H10B 0.9800 . ?
C10A H10C 0.9800 . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11C 0.9800 . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A H12C 0.9800 . ?
C13A C14A 1.384(9) . ?
C13A C15A 1.470(10) . ?
C14A C17A 1.417(9) . ?
C15A C16A 1.504(9) . ?
C16A H16A 0.9800 . ?
C16A H16B 0.9800 . ?
C16A H16C 0.9800 . ?
C17A H17A 0.9500 . ?
C17A C18A 1.391(10) . ?
C18A C19A 1.415(10) . ?
C18A C21A 1.439(10) . ?
C19A H19A 0.9500 . ?
C19A C20A 1.327(9) . ?
C20A H20A 0.9500 . ?
Br1B C4B 1.897(7) . ?
Si1B C9B 1.893(7) . ?
Si1B C10B 1.877(6) . ?
Si1B C11B 1.844(7) . ?
Si1B C12B 1.864(7) . ?
O1B C7B 1.229(8) . ?
O2B C15B 1.222(8) . ?
N1B C8B 1.389(8) . ?
N1B C14B 1.402(8) . ?
N1B C20B 1.380(8) . ?
N2B C21B 1.142(8) . ?
C1B C2B 1.395(9) . ?
C1B C6B 1.369(10) . ?
C1B C7B 1.473(9) . ?
C2B H2B 0.9500 . ?
C2B C3B 1.381(10) . ?
C3B H3B 0.9500 . ?
C3B C4B 1.359(10) . ?
C4B C5B 1.389(10) . ?
C5B H5B 0.9500 . ?
C5B C6B 1.382(10) . ?
C6B H6B 0.9500 . ?
C7B C8B 1.510(9) . ?
C8B C9B 1.374(9) . ?
C9B C13B 1.447(8) . ?
C10B H10D 0.9800 . ?
C10B H10E 0.9800 . ?
C10B H10F 0.9800 . ?
C11B H11D 0.9800 . ?
C11B H11E 0.9800 . ?
C11B H11F 0.9800 . ?
C12B H12D 0.9800 . ?
C12B H12E 0.9800 . ?
C12B H12F 0.9800 . ?
C13B C14B 1.397(9) . ?
C13B C15B 1.467(9) . ?
C14B C17B 1.406(8) . ?
C15B C16B 1.496(8) . ?
C16B H16D 0.9800 . ?
C16B H16E 0.9800 . ?
C16B H16F 0.9800 . ?
C17B H17B 0.9500 . ?
C17B C18B 1.342(9) . ?
C18B C19B 1.431(9) . ?
C18B C21B 1.461(10) . ?
C19B H19B 0.9500 . ?
C19B C20B 1.350(9) . ?
C20B H20B 0.9500 . ?
Br1C C4C 1.901(7) . ?
Si1C C9C 1.887(7) . ?
Si1C C10C 1.848(8) . ?
Si1C C11C 1.871(7) . ?
Si1C C12C 1.837(8) . ?
O1C C7C 1.226(8) . ?
O2C C15C 1.222(8) . ?
N1C C8C 1.387(8) . ?
N1C C14C 1.404(8) . ?
N1C C20C 1.385(9) . ?
N2C C21C 1.138(9) . ?
C1C C2C 1.392(10) . ?
C1C C6C 1.380(10) . ?
C1C C7C 1.479(9) . ?
C2C H2C 0.9500 . ?
C2C C3C 1.383(10) . ?
C3C H3C 0.9500 . ?
C3C C4C 1.384(10) . ?
C4C C5C 1.364(10) . ?
C5C H5C 0.9500 . ?
C5C C6C 1.393(10) . ?
C6C H6C 0.9500 . ?
C7C C8C 1.480(9) . ?
C8C C9C 1.388(9) . ?
C9C C13C 1.435(9) . ?
C10C H10G 0.9800 . ?
C10C H10H 0.9800 . ?
C10C H10I 0.9800 . ?
C11C H11G 0.9800 . ?
C11C H11H 0.9800 . ?
C11C H11I 0.9800 . ?
C12C H12G 0.9800 . ?
C12C H12H 0.9800 . ?
C12C H12I 0.9800 . ?
C13C C14C 1.398(9) . ?
C13C C15C 1.474(10) . ?
C14C C17C 1.421(9) . ?
C15C C16C 1.501(10) . ?
C16C H16G 0.9800 . ?
C16C H16H 0.9800 . ?
C16C H16I 0.9800 . ?
C17C H17C 0.9500 . ?
C17C C18C 1.358(10) . ?
C18C C19C 1.436(9) . ?
C18C C21C 1.444(10) . ?
C19C H19C 0.9500 . ?
C19C C20C 1.340(9) . ?
C20C H20C 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
C10A Si1A C9A 110.2(3) . . ?
C11A Si1A C9A 112.6(3) . . ?
C11A Si1A C10A 107.3(3) . . ?
C11A Si1A C12A 112.1(4) . . ?
C12A Si1A C9A 110.0(3) . . ?
C12A Si1A C10A 104.3(3) . . ?
C8A N1A C14A 109.0(6) . . ?
C8A N1A C20A 129.8(6) . . ?
C20A N1A C14A 121.1(6) . . ?
C2A C1A C7A 119.6(7) . . ?
C6A C1A C2A 119.7(7) . . ?
C6A C1A C7A 120.7(7) . . ?
C1A C2A H2A 119.4 . . ?
C3A C2A C1A 121.2(7) . . ?
C3A C2A H2A 119.4 . . ?
C2A C3A H3A 121.0 . . ?
C2A C3A C4A 118.0(7) . . ?
C4A C3A H3A 121.0 . . ?
C3A C4A Br1A 119.4(6) . . ?
C3A C4A C5A 121.9(7) . . ?
C5A C4A Br1A 118.7(6) . . ?
C4A C5A H5A 120.7 . . ?
C6A C5A C4A 118.7(7) . . ?
C6A C5A H5A 120.7 . . ?
C1A C6A C5A 120.5(7) . . ?
C1A C6A H6A 119.7 . . ?
C5A C6A H6A 119.7 . . ?
O1A C7A C1A 122.2(7) . . ?
O1A C7A C8A 120.0(7) . . ?
C1A C7A C8A 117.8(7) . . ?
N1A C8A C7A 121.9(6) . . ?
N1A C8A C9A 109.3(6) . . ?
C9A C8A C7A 128.8(6) . . ?
C8A C9A Si1A 125.9(5) . . ?
C8A C9A C13A 105.9(6) . . ?
C13A C9A Si1A 127.2(6) . . ?
Si1A C10A H10A 109.5 . . ?
Si1A C10A H10B 109.5 . . ?
Si1A C10A H10C 109.5 . . ?
H10A C10A H10B 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
Si1A C11A H11A 109.5 . . ?
Si1A C11A H11B 109.5 . . ?
Si1A C11A H11C 109.5 . . ?
H11A C11A H11B 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
Si1A C12A H12A 109.5 . . ?
Si1A C12A H12B 109.5 . . ?
Si1A C12A H12C 109.5 . . ?
H12A C12A H12B 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C9A C13A C15A 122.6(6) . . ?
C14A C13A C9A 109.3(6) . . ?
C14A C13A C15A 127.9(6) . . ?
N1A C14A C17A 117.5(7) . . ?
C13A C14A N1A 106.4(6) . . ?
C13A C14A C17A 136.0(7) . . ?
O2A C15A C13A 119.1(7) . . ?
O2A C15A C16A 120.0(7) . . ?
C13A C15A C16A 120.8(6) . . ?
C15A C16A H16A 109.5 . . ?
C15A C16A H16B 109.5 . . ?
C15A C16A H16C 109.5 . . ?
H16A C16A H16B 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
C14A C17A H17A 120.4 . . ?
C18A C17A C14A 119.2(7) . . ?
C18A C17A H17A 120.4 . . ?
C17A C18A C19A 121.3(7) . . ?
C17A C18A C21A 119.7(7) . . ?
C19A C18A C21A 119.0(7) . . ?
C18A C19A H19A 120.1 . . ?
C20A C19A C18A 119.8(7) . . ?
C20A C19A H19A 120.1 . . ?
N1A C20A H20A 119.6 . . ?
C19A C20A N1A 120.8(7) . . ?
C19A C20A H20A 119.6 . . ?
N2A C21A C18A 179.9(11) . . ?
C10B Si1B C9B 108.2(3) . . ?
C11B Si1B C9B 112.5(3) . . ?
C11B Si1B C10B 107.6(3) . . ?
C11B Si1B C12B 112.6(4) . . ?
C12B Si1B C9B 110.4(3) . . ?
C12B Si1B C10B 105.2(3) . . ?
C8B N1B C14B 108.1(6) . . ?
C20B N1B C8B 129.4(6) . . ?
C20B N1B C14B 122.5(5) . . ?
C2B C1B C7B 119.7(7) . . ?
C6B C1B C2B 118.0(7) . . ?
C6B C1B C7B 122.3(7) . . ?
C1B C2B H2B 119.6 . . ?
C3B C2B C1B 120.8(7) . . ?
C3B C2B H2B 119.6 . . ?
C2B C3B H3B 120.2 . . ?
C4B C3B C2B 119.7(7) . . ?
C4B C3B H3B 120.2 . . ?
C3B C4B Br1B 120.3(6) . . ?
C3B C4B C5B 121.3(7) . . ?
C5B C4B Br1B 118.4(6) . . ?
C4B C5B H5B 121.0 . . ?
C6B C5B C4B 118.0(7) . . ?
C6B C5B H5B 121.0 . . ?
C1B C6B C5B 122.3(7) . . ?
C1B C6B H6B 118.8 . . ?
C5B C6B H6B 118.8 . . ?
O1B C7B C1B 122.8(6) . . ?
O1B C7B C8B 117.7(7) . . ?
C1B C7B C8B 119.5(6) . . ?
N1B C8B C7B 119.0(6) . . ?
C9B C8B N1B 110.4(6) . . ?
C9B C8B C7B 130.6(6) . . ?
C8B C9B Si1B 127.0(5) . . ?
C8B C9B C13B 105.8(6) . . ?
C13B C9B Si1B 126.1(5) . . ?
Si1B C10B H10D 109.5 . . ?
Si1B C10B H10E 109.5 . . ?
Si1B C10B H10F 109.5 . . ?
H10D C10B H10E 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
Si1B C11B H11D 109.5 . . ?
Si1B C11B H11E 109.5 . . ?
Si1B C11B H11F 109.5 . . ?
H11D C11B H11E 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
Si1B C12B H12D 109.5 . . ?
Si1B C12B H12E 109.5 . . ?
Si1B C12B H12F 109.5 . . ?
H12D C12B H12E 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
C9B C13B C15B 122.8(6) . . ?
C14B C13B C9B 108.2(6) . . ?
C14B C13B C15B 129.0(6) . . ?
N1B C14B C17B 116.6(6) . . ?
C13B C14B N1B 107.4(5) . . ?
C13B C14B C17B 135.9(6) . . ?
O2B C15B C13B 119.0(6) . . ?
O2B C15B C16B 119.7(7) . . ?
C13B C15B C16B 121.3(6) . . ?
C15B C16B H16D 109.5 . . ?
C15B C16B H16E 109.5 . . ?
C15B C16B H16F 109.5 . . ?
H16D C16B H16E 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?
C14B C17B H17B 119.7 . . ?
C18B C17B C14B 120.6(6) . . ?
C18B C17B H17B 119.7 . . ?
C17B C18B C19B 121.7(6) . . ?
C17B C18B C21B 121.7(6) . . ?
C19B C18B C21B 116.7(6) . . ?
C18B C19B H19B 120.9 . . ?
C20B C19B C18B 118.3(7) . . ?
C20B C19B H19B 120.9 . . ?
N1B C20B H20B 120.0 . . ?
C19B C20B N1B 120.1(6) . . ?
C19B C20B H20B 120.0 . . ?
N2B C21B C18B 176.9(9) . . ?
C10C Si1C C9C 110.8(3) . . ?
C10C Si1C C11C 106.3(4) . . ?
C11C Si1C C9C 109.2(3) . . ?
C12C Si1C C9C 112.1(3) . . ?
C12C Si1C C10C 109.9(4) . . ?
C12C Si1C C11C 108.4(4) . . ?
C8C N1C C14C 109.5(6) . . ?
C20C N1C C8C 129.0(6) . . ?
C20C N1C C14C 121.5(6) . . ?
C2C C1C C7C 120.1(7) . . ?
C6C C1C C2C 119.3(7) . . ?
C6C C1C C7C 120.5(7) . . ?
C1C C2C H2C 120.0 . . ?
C3C C2C C1C 119.9(8) . . ?
C3C C2C H2C 120.0 . . ?
C2C C3C H3C 120.2 . . ?
C2C C3C C4C 119.6(8) . . ?
C4C C3C H3C 120.2 . . ?
C3C C4C Br1C 119.1(6) . . ?
C5C C4C Br1C 119.6(6) . . ?
C5C C4C C3C 121.3(7) . . ?
C4C C5C H5C 120.5 . . ?
C4C C5C C6C 118.9(7) . . ?
C6C C5C H5C 120.5 . . ?
C1C C6C C5C 120.8(8) . . ?
C1C C6C H6C 119.6 . . ?
C5C C6C H6C 119.6 . . ?
O1C C7C C1C 121.2(6) . . ?
O1C C7C C8C 119.1(6) . . ?
C1C C7C C8C 119.6(6) . . ?
N1C C8C C7C 120.9(6) . . ?
N1C C8C C9C 109.2(6) . . ?
C9C C8C C7C 129.9(7) . . ?
C8C C9C Si1C 125.9(5) . . ?
C8C C9C C13C 105.9(6) . . ?
C13C C9C Si1C 127.2(6) . . ?
Si1C C10C H10G 109.5 . . ?
Si1C C10C H10H 109.5 . . ?
Si1C C10C H10I 109.5 . . ?
H10G C10C H10H 109.5 . . ?
H10G C10C H10I 109.5 . . ?
H10H C10C H10I 109.5 . . ?
Si1C C11C H11G 109.5 . . ?
Si1C C11C H11H 109.5 . . ?
Si1C C11C H11I 109.5 . . ?
H11G C11C H11H 109.5 . . ?
H11G C11C H11I 109.5 . . ?
H11H C11C H11I 109.5 . . ?
Si1C C12C H12G 109.5 . . ?
Si1C C12C H12H 109.5 . . ?
Si1C C12C H12I 109.5 . . ?
H12G C12C H12H 109.5 . . ?
H12G C12C H12I 109.5 . . ?
H12H C12C H12I 109.5 . . ?
C9C C13C C15C 123.6(7) . . ?
C14C C13C C9C 109.4(7) . . ?
C14C C13C C15C 126.8(6) . . ?
N1C C14C C17C 117.1(6) . . ?
C13C C14C N1C 106.1(6) . . ?
C13C C14C C17C 136.8(7) . . ?
O2C C15C C13C 119.4(7) . . ?
O2C C15C C16C 120.6(7) . . ?
C13C C15C C16C 120.0(7) . . ?
C15C C16C H16G 109.5 . . ?
C15C C16C H16H 109.5 . . ?
C15C C16C H16I 109.5 . . ?
H16G C16C H16H 109.5 . . ?
H16G C16C H16I 109.5 . . ?
H16H C16C H16I 109.5 . . ?
C14C C17C H17C 119.9 . . ?
C18C C17C C14C 120.1(7) . . ?
C18C C17C H17C 119.9 . . ?
C17C C18C C19C 121.5(7) . . ?
C17C C18C C21C 121.1(7) . . ?
C19C C18C C21C 117.4(7) . . ?
C18C C19C H19C 121.0 . . ?
C20C C19C C18C 118.1(7) . . ?
C20C C19C H19C 121.0 . . ?
N1C C20C H20C 119.2 . . ?
C19C C20C N1C 121.7(7) . . ?
C19C C20C H20C 119.2 . . ?
N2C C21C C18C 177.4(9) . . ?

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
Br1A C4A C5A C6A 177.3(5) . . . . ?
Si1A C9A C13A C14A 166.8(5) . . . . ?
Si1A C9A C13A C15A -17.7(10) . . . . ?
O1A C7A C8A N1A -126.9(8) . . . . ?
O1A C7A C8A C9A 53.0(11) . . . . ?
N1A C8A C9A Si1A -168.6(5) . . . . ?
N1A C8A C9A C13A 0.4(8) . . . . ?
N1A C14A C17A C18A 0.0(10) . . . . ?
C1A C2A C3A C4A -0.2(11) . . . . ?
C1A C7A C8A N1A 53.7(9) . . . . ?
C1A C7A C8A C9A -126.5(8) . . . . ?
C2A C1A C6A C5A 1.6(11) . . . . ?
C2A C1A C7A O1A 21.8(11) . . . . ?
C2A C1A C7A C8A -158.7(7) . . . . ?
C2A C3A C4A Br1A -177.8(5) . . . . ?
C2A C3A C4A C5A 3.0(11) . . . . ?
C3A C4A C5A C6A -3.4(10) . . . . ?
C4A C5A C6A C1A 1.1(10) . . . . ?
C6A C1A C2A C3A -2.1(11) . . . . ?
C6A C1A C7A O1A -158.9(7) . . . . ?
C6A C1A C7A C8A 20.6(10) . . . . ?
C7A C1A C2A C3A 177.2(6) . . . . ?
C7A C1A C6A C5A -177.7(6) . . . . ?
C7A C8A C9A Si1A 11.5(11) . . . . ?
C7A C8A C9A C13A -179.5(7) . . . . ?
C8A N1A C14A C13A -2.6(8) . . . . ?
C8A N1A C14A C17A 178.6(6) . . . . ?
C8A N1A C20A C19A -178.9(7) . . . . ?
C8A C9A C13A C14A -2.0(8) . . . . ?
C8A C9A C13A C15A 173.5(7) . . . . ?
C9A C13A C14A N1A 2.8(8) . . . . ?
C9A C13A C14A C17A -178.6(8) . . . . ?
C9A C13A C15A O2A -13.5(11) . . . . ?
C9A C13A C15A C16A 167.7(7) . . . . ?
C10A Si1A C9A C8A 12.5(8) . . . . ?
C10A Si1A C9A C13A -154.2(6) . . . . ?
C11A Si1A C9A C8A -107.2(7) . . . . ?
C11A Si1A C9A C13A 86.1(7) . . . . ?
C12A Si1A C9A C8A 127.0(7) . . . . ?
C12A Si1A C9A C13A -39.7(7) . . . . ?
C13A C14A C17A C18A -178.5(9) . . . . ?
C14A N1A C8A C7A -178.8(6) . . . . ?
C14A N1A C8A C9A 1.3(8) . . . . ?
C14A N1A C20A C19A 5.1(11) . . . . ?
C14A C13A C15A O2A 161.0(8) . . . . ?
C14A C13A C15A C16A -17.7(12) . . . . ?
C14A C17A C18A C19A 4.4(11) . . . . ?
C14A C17A C18A C21A -175.3(7) . . . . ?
C15A C13A C14A N1A -172.4(7) . . . . ?
C15A C13A C14A C17A 6.2(15) . . . . ?
C17A C18A C19A C20A -4.2(11) . . . . ?
C18A C19A C20A N1A -0.6(11) . . . . ?
C20A N1A C8A C7A 4.8(11) . . . . ?
C20A N1A C8A C9A -175.1(7) . . . . ?
C20A N1A C14A C13A 174.2(6) . . . . ?
C20A N1A C14A C17A -4.7(10) . . . . ?
C21A C18A C19A C20A 175.5(7) . . . . ?
Br1B C4B C5B C6B -178.2(6) . . . . ?
Si1B C9B C13B C14B -167.2(5) . . . . ?
Si1B C9B C13B C15B 14.3(10) . . . . ?
O1B C7B C8B N1B 121.3(7) . . . . ?
O1B C7B C8B C9B -56.4(11) . . . . ?
N1B C8B C9B Si1B 167.9(5) . . . . ?
N1B C8B C9B C13B -0.8(8) . . . . ?
N1B C14B C17B C18B -1.2(10) . . . . ?
C1B C2B C3B C4B 0.2(12) . . . . ?
C1B C7B C8B N1B -59.9(9) . . . . ?
C1B C7B C8B C9B 122.4(9) . . . . ?
C2B C1B C6B C5B 0.7(12) . . . . ?
C2B C1B C7B O1B -17.6(11) . . . . ?
C2B C1B C7B C8B 163.7(6) . . . . ?
C2B C3B C4B Br1B 178.2(6) . . . . ?
C2B C3B C4B C5B 0.2(12) . . . . ?
C3B C4B C5B C6B -0.1(12) . . . . ?
C4B C5B C6B C1B -0.3(12) . . . . ?
C6B C1B C2B C3B -0.6(11) . . . . ?
C6B C1B C7B O1B 163.3(7) . . . . ?
C6B C1B C7B C8B -15.4(10) . . . . ?
C7B C1B C2B C3B -179.7(7) . . . . ?
C7B C1B C6B C5B 179.8(7) . . . . ?
C7B C8B C9B Si1B -14.3(12) . . . . ?
C7B C8B C9B C13B 177.0(7) . . . . ?
C8B N1B C14B C13B 1.3(8) . . . . ?
C8B N1B C14B C17B -176.5(6) . . . . ?
C8B N1B C20B C19B 177.4(7) . . . . ?
C8B C9B C13B C14B 1.6(8) . . . . ?
C8B C9B C13B C15B -176.8(7) . . . . ?
C9B C13B C14B N1B -1.8(8) . . . . ?
C9B C13B C14B C17B 175.3(8) . . . . ?
C9B C13B C15B O2B 4.2(11) . . . . ?
C9B C13B C15B C16B -179.5(7) . . . . ?
C10B Si1B C9B C8B -4.9(8) . . . . ?
C10B Si1B C9B C13B 161.6(6) . . . . ?
C11B Si1B C9B C8B 113.8(7) . . . . ?
C11B Si1B C9B C13B -79.7(7) . . . . ?
C12B Si1B C9B C8B -119.5(7) . . . . ?
C12B Si1B C9B C13B 47.0(7) . . . . ?
C13B C14B C17B C18B -178.1(8) . . . . ?
C14B N1B C8B C7B -178.4(6) . . . . ?
C14B N1B C8B C9B -0.3(8) . . . . ?
C14B N1B C20B C19B -4.8(11) . . . . ?
C14B C13B C15B O2B -173.9(8) . . . . ?
C14B C13B C15B C16B 2.4(12) . . . . ?
C14B C17B C18B C19B -3.4(11) . . . . ?
C14B C17B C18B C21B 174.7(7) . . . . ?
C15B C13B C14B N1B 176.5(7) . . . . ?
C15B C13B C14B C17B -6.3(15) . . . . ?
C17B C18B C19B C20B 4.0(11) . . . . ?
C18B C19B C20B N1B 0.1(11) . . . . ?
C20B N1B C8B C7B -0.4(11) . . . . ?
C20B N1B C8B C9B 177.7(7) . . . . ?
C20B N1B C14B C13B -176.9(7) . . . . ?
C20B N1B C14B C17B 5.3(10) . . . . ?
C21B C18B C19B C20B -174.2(7) . . . . ?
Br1C C4C C5C C6C -179.7(6) . . . . ?
Si1C C9C C13C C14C 169.8(5) . . . . ?
Si1C C9C C13C C15C -15.5(10) . . . . ?
O1C C7C C8C N1C -125.2(8) . . . . ?
O1C C7C C8C C9C 52.3(11) . . . . ?
N1C C8C C9C Si1C -170.9(5) . . . . ?
N1C C8C C9C C13C -1.6(8) . . . . ?
N1C C14C C17C C18C 1.7(11) . . . . ?
C1C C2C C3C C4C 0.4(11) . . . . ?
C1C C7C C8C N1C 56.2(9) . . . . ?
C1C C7C C8C C9C -126.3(8) . . . . ?
C2C C1C C6C C5C -1.5(11) . . . . ?
C2C C1C C7C O1C -152.1(7) . . . . ?
C2C C1C C7C C8C 26.4(10) . . . . ?
C2C C3C C4C Br1C 178.1(5) . . . . ?
C2C C3C C4C C5C 0.8(12) . . . . ?
C3C C4C C5C C6C -2.3(12) . . . . ?
C4C C5C C6C C1C 2.7(12) . . . . ?
C6C C1C C2C C3C -0.1(11) . . . . ?
C6C C1C C7C O1C 25.2(11) . . . . ?
C6C C1C C7C C8C -156.3(7) . . . . ?
C7C C1C C2C C3C 177.2(7) . . . . ?
C7C C1C C6C C5C -178.8(7) . . . . ?
C7C C8C C9C Si1C 11.4(11) . . . . ?
C7C C8C C9C C13C -179.4(7) . . . . ?
C8C N1C C14C C13C -1.5(8) . . . . ?
C8C N1C C14C C17C -179.7(6) . . . . ?
C8C N1C C20C C19C 177.4(7) . . . . ?
C8C C9C C13C C14C 0.7(8) . . . . ?
C8C C9C C13C C15C 175.4(6) . . . . ?
C9C C13C C14C N1C 0.5(8) . . . . ?
C9C C13C C14C C17C 178.2(8) . . . . ?
C9C C13C C15C O2C -19.6(11) . . . . ?
C9C C13C C15C C16C 161.9(7) . . . . ?
C10C Si1C C9C C8C 132.0(7) . . . . ?
C10C Si1C C9C C13C -35.0(7) . . . . ?
C11C Si1C C9C C8C 15.3(8) . . . . ?
C11C Si1C C9C C13C -151.7(6) . . . . ?
C12C Si1C C9C C8C -104.8(7) . . . . ?
C12C Si1C C9C C13C 88.2(7) . . . . ?
C13C C14C C17C C18C -175.8(8) . . . . ?
C14C N1C C8C C7C 180.0(6) . . . . ?
C14C N1C C8C C9C 2.0(8) . . . . ?
C14C N1C C20C C19C 1.5(11) . . . . ?
C14C C13C C15C O2C 154.2(8) . . . . ?
C14C C13C C15C C16C -24.4(11) . . . . ?
C14C C17C C18C C19C 1.3(12) . . . . ?
C14C C17C C18C C21C -179.2(7) . . . . ?
C15C C13C C14C N1C -174.0(6) . . . . ?
C15C C13C C14C C17C 3.7(15) . . . . ?
C17C C18C C19C C20C -3.0(11) . . . . ?
C18C C19C C20C N1C 1.5(11) . . . . ?
C20C N1C C8C C7C 3.7(11) . . . . ?
C20C N1C C8C C9C -174.3(7) . . . . ?
C20C N1C C14C C13C 175.1(6) . . . . ?
C20C N1C C14C C17C -3.2(10) . . . . ?
C21C C18C C19C C20C 177.5(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 10.516
_oxdiff_exptl_absorpt_empirical_full_min 0.718
####################################################################### 
# 
# 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_shi_4953_elba_auto
_database_code_depnum_ccdc_archive 'CCDC 2213000'
loop_
_audit_author_name
_audit_author_address
'Sergiu shova'
;Institute of Macromolecular Chemistry, Iasi
Romania
;
_audit_update_record             
;
2022-10-14 deposited with the CCDC.	2023-01-09 downloaded from the CCDC.
;
_audit_creation_date             2022-07-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H19 Br N2 O2 Si'
_chemical_formula_sum            'C21 H19 Br N2 O2 Si'
_chemical_formula_weight         439.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N2Si1O2Br1
_chemical_oxdiff_usercomment     AZD_35_FR5-7
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'
Si Si 0.0817 0.0704 '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                   9.7796(7)
_cell_length_b                   10.0750(10)
_cell_length_c                   11.8548(8)
_cell_angle_alpha                114.403(8)
_cell_angle_beta                 100.557(6)
_cell_angle_gamma                92.945(7)
_cell_volume                     1035.10(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3047
_cell_measurement_temperature    239.95(10)
_cell_measurement_theta_max      26.3120
_cell_measurement_theta_min      1.9330
_shelx_estimated_absorpt_T_max   0.820
_shelx_estimated_absorpt_T_min   0.683
_exptl_absorpt_coefficient_mu    2.061
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0604
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9117
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         1.936
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      239.95(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1593
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     25.00  54.00   1.00    5.00    --  -15.44  33.00 113.00   29
  2  ω    -52.00  38.00   1.00    5.00    --   17.94 -33.00 -45.00   90
  3  ω     12.00  88.00   1.00    5.00    --   17.94  33.00 113.00   76
  4  ω    -27.00   4.00   1.00    5.00    --  -15.44 -77.00-180.00   31
  5  ω    -88.00 -39.00   1.00    5.00    --  -15.44-178.00 120.00   49
  6  ω    -39.00   0.00   1.00    5.00    --  -15.44 -77.00 -90.00   39
  7  ω    -82.00 -56.00   1.00    5.00    --  -15.44 178.00-180.00   26
  8  ω    -33.00   1.00   1.00    5.00    --  -15.44 -77.00 120.00   34
  9  ω    -19.00  31.00   1.00    5.00    --   17.94 -99.00 120.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0465047000
_diffrn_orient_matrix_UB_12      0.0512164000
_diffrn_orient_matrix_UB_13      0.0236800000
_diffrn_orient_matrix_UB_21      0.0535148000
_diffrn_orient_matrix_UB_22      0.0589115000
_diffrn_orient_matrix_UB_23      0.0153845000
_diffrn_orient_matrix_UB_31      -0.0229893000
_diffrn_orient_matrix_UB_32      -0.0024074000
_diffrn_orient_matrix_UB_33      -0.0612295000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2951
_reflns_number_total             4166
_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       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         4166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0453
_refine_ls_restrained_S_all      1.014
_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)+(0.0474P)²+0.0140P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.1076
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C17(H17), C19(H19), C20(H20)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C)
;
_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
Br1 Br 0.07814(4) 0.79023(5) 1.09088(3) 0.06763(19) Uani 1 1 d . . . . .
Si1 Si 0.27571(9) 0.51382(9) 0.29629(7) 0.0332(2) Uani 1 1 d . . . . .
O1 O 0.4716(2) 1.1030(2) 0.82022(18) 0.0430(6) Uani 1 1 d . . . . .
O2 O 0.1815(2) 0.5530(2) 0.5672(2) 0.0468(6) Uani 1 1 d . . . . .
N1 N 0.5182(2) 0.8851(2) 0.58763(19) 0.0261(5) Uani 1 1 d . . . . .
N2 N 0.8988(3) 0.8390(4) 0.3088(3) 0.0608(9) Uani 1 1 d . . . . .
C1 C 0.3360(3) 0.9271(4) 0.8533(2) 0.0335(7) Uani 1 1 d . . . . .
C2 C 0.2630(3) 1.0266(4) 0.9324(3) 0.0456(9) Uani 1 1 d . . . . .
H2 H 0.264457 1.122252 0.937279 0.055 Uiso 1 1 calc R U . . .
C3 C 0.1879(3) 0.9849(4) 1.0040(3) 0.0531(10) Uani 1 1 d . . . . .
H3 H 0.138002 1.051608 1.057193 0.064 Uiso 1 1 calc R U . . .
C4 C 0.1873(3) 0.8457(4) 0.9965(3) 0.0448(9) Uani 1 1 d . . . . .
C5 C 0.2634(3) 0.7471(4) 0.9233(3) 0.0462(9) Uani 1 1 d . . . . .
H5 H 0.265412 0.653439 0.922186 0.055 Uiso 1 1 calc R U . . .
C6 C 0.3373(3) 0.7891(4) 0.8509(3) 0.0394(8) Uani 1 1 d . . . . .
H6 H 0.388852 0.722509 0.799624 0.047 Uiso 1 1 calc R U . . .
C7 C 0.4127(3) 0.9769(3) 0.7761(2) 0.0319(7) Uani 1 1 d . . . . .
C8 C 0.4133(3) 0.8699(3) 0.6474(2) 0.0267(6) Uani 1 1 d . . . . .
C9 C 0.3204(3) 0.7434(3) 0.5596(2) 0.0259(6) Uani 1 1 d . . . . .
C10 C 0.1895(3) 0.6779(3) 0.5784(2) 0.0314(7) Uani 1 1 d . . . . .
C11 C 0.0707(3) 0.7655(4) 0.6019(3) 0.0444(8) Uani 1 1 d . . . . .
H11A H -0.001837 0.712975 0.620081 0.067 Uiso 1 1 calc R U . . .
H11B H 0.032159 0.779985 0.527054 0.067 Uiso 1 1 calc R U . . .
H11C H 0.104493 0.860358 0.673812 0.067 Uiso 1 1 calc R U . . .
C12 C 0.3664(3) 0.6807(3) 0.4451(2) 0.0261(6) Uani 1 1 d . . . . .
C13 C 0.0840(3) 0.5201(4) 0.2650(3) 0.0479(9) Uani 1 1 d . . . . .
H13A H 0.046152 0.511208 0.332103 0.072 Uiso 1 1 calc R U . . .
H13B H 0.038680 0.439459 0.184008 0.072 Uiso 1 1 calc R U . . .
H13C H 0.066750 0.612926 0.262533 0.072 Uiso 1 1 calc R U . . .
C14 C 0.3158(4) 0.3463(3) 0.3180(3) 0.0555(10) Uani 1 1 d . . . . .
H14A H 0.416826 0.349679 0.340550 0.083 Uiso 1 1 calc R U . . .
H14B H 0.276771 0.259441 0.239459 0.083 Uiso 1 1 calc R U . . .
H14C H 0.274749 0.342490 0.385316 0.083 Uiso 1 1 calc R U . . .
C15 C 0.3388(4) 0.5095(4) 0.1553(3) 0.0530(10) Uani 1 1 d . . . . .
H15A H 0.344932 0.607176 0.158004 0.080 Uiso 1 1 calc R U . . .
H15B H 0.273468 0.441268 0.078004 0.080 Uiso 1 1 calc R U . . .
H15C H 0.430864 0.477745 0.156864 0.080 Uiso 1 1 calc R U . . .
C16 C 0.4908(3) 0.7688(3) 0.4653(2) 0.0262(6) Uani 1 1 d . . . . .
C17 C 0.5925(3) 0.7601(3) 0.3924(3) 0.0323(7) Uani 1 1 d . . . . .
H17 H 0.577159 0.685277 0.309219 0.039 Uiso 1 1 calc R U . . .
C18 C 0.7123(3) 0.8587(3) 0.4415(3) 0.0332(7) Uani 1 1 d . . . . .
C19 C 0.7365(3) 0.9739(3) 0.5665(3) 0.0351(7) Uani 1 1 d . . . . .
H19 H 0.819496 1.041602 0.600204 0.042 Uiso 1 1 calc R U . . .
C20 C 0.6399(3) 0.9853(3) 0.6363(3) 0.0334(7) Uani 1 1 d . . . . .
H20 H 0.655243 1.061916 0.718696 0.040 Uiso 1 1 calc R U . . .
C21 C 0.8150(3) 0.8462(4) 0.3664(3) 0.0420(8) 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
Br1 C4 1.897(3) . ?
Si1 C12 1.883(3) . ?
Si1 C13 1.853(3) . ?
Si1 C14 1.859(3) . ?
Si1 C15 1.870(3) . ?
O1 C7 1.218(3) . ?
O2 C10 1.206(3) . ?
N1 C8 1.385(3) . ?
N1 C16 1.403(3) . ?
N1 C20 1.383(3) . ?
N2 C21 1.146(4) . ?
C1 C2 1.391(4) . ?
C1 C6 1.379(4) . ?
C1 C7 1.499(4) . ?
C2 H2 0.9400 . ?
C2 C3 1.390(4) . ?
C3 H3 0.9400 . ?
C3 C4 1.367(5) . ?
C4 C5 1.376(5) . ?
C5 H5 0.9400 . ?
C5 C6 1.390(4) . ?
C6 H6 0.9400 . ?
C7 C8 1.461(4) . ?
C8 C9 1.404(4) . ?
C9 C10 1.504(4) . ?
C9 C12 1.410(3) . ?
C10 C11 1.492(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C12 C16 1.390(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?
C16 C17 1.416(3) . ?
C17 H17 0.9400 . ?
C17 C18 1.360(4) . ?
C18 C19 1.422(4) . ?
C18 C21 1.437(4) . ?
C19 H19 0.9400 . ?
C19 C20 1.345(4) . ?
C20 H20 0.9400 . ?

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
C13 Si1 C12 109.65(13) . . ?
C13 Si1 C14 111.30(16) . . ?
C13 Si1 C15 107.50(15) . . ?
C14 Si1 C12 108.48(14) . . ?
C14 Si1 C15 108.95(16) . . ?
C15 Si1 C12 110.97(14) . . ?
C8 N1 C16 108.7(2) . . ?
C20 N1 C8 129.2(2) . . ?
C20 N1 C16 121.9(2) . . ?
C2 C1 C7 117.8(3) . . ?
C6 C1 C2 119.3(3) . . ?
C6 C1 C7 122.9(3) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.1(3) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.3(3) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 Br1 118.1(2) . . ?
C3 C4 C5 121.8(3) . . ?
C5 C4 Br1 120.1(3) . . ?
C4 C5 H5 120.7 . . ?
C4 C5 C6 118.6(3) . . ?
C6 C5 H5 120.7 . . ?
C1 C6 C5 120.9(3) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
O1 C7 C1 120.4(3) . . ?
O1 C7 C8 121.8(3) . . ?
C8 C7 C1 117.8(3) . . ?
N1 C8 C7 121.2(2) . . ?
N1 C8 C9 106.3(2) . . ?
C9 C8 C7 132.5(2) . . ?
C8 C9 C10 127.4(2) . . ?
C8 C9 C12 110.2(2) . . ?
C12 C9 C10 122.4(2) . . ?
O2 C10 C9 118.5(3) . . ?
O2 C10 C11 122.2(3) . . ?
C11 C10 C9 119.2(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 Si1 126.8(2) . . ?
C16 C12 Si1 127.77(18) . . ?
C16 C12 C9 105.5(2) . . ?
Si1 C13 H13A 109.5 . . ?
Si1 C13 H13B 109.5 . . ?
Si1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
Si1 C14 H14A 109.5 . . ?
Si1 C14 H14B 109.5 . . ?
Si1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
Si1 C15 H15A 109.5 . . ?
Si1 C15 H15B 109.5 . . ?
Si1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 C17 116.9(2) . . ?
C12 C16 N1 109.4(2) . . ?
C12 C16 C17 133.7(2) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.8(3) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 C19 120.4(2) . . ?
C17 C18 C21 119.7(3) . . ?
C19 C18 C21 119.8(3) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 C18 119.6(3) . . ?
C20 C19 H19 120.2 . . ?
N1 C20 H20 119.8 . . ?
C19 C20 N1 120.4(3) . . ?
C19 C20 H20 119.8 . . ?
N2 C21 C18 178.4(4) . . ?

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
Br1 C4 C5 C6 177.2(2) . . . . ?
Si1 C12 C16 N1 177.62(19) . . . . ?
Si1 C12 C16 C17 -5.8(5) . . . . ?
O1 C7 C8 N1 24.2(4) . . . . ?
O1 C7 C8 C9 -153.8(3) . . . . ?
N1 C8 C9 C10 179.4(3) . . . . ?
N1 C8 C9 C12 -0.6(3) . . . . ?
N1 C16 C17 C18 1.5(4) . . . . ?
C1 C2 C3 C4 0.4(5) . . . . ?
C1 C7 C8 N1 -156.1(3) . . . . ?
C1 C7 C8 C9 25.8(5) . . . . ?
C2 C1 C6 C5 1.9(4) . . . . ?
C2 C1 C7 O1 37.0(4) . . . . ?
C2 C1 C7 C8 -142.6(3) . . . . ?
C2 C3 C4 Br1 -177.7(2) . . . . ?
C2 C3 C4 C5 2.4(5) . . . . ?
C3 C4 C5 C6 -3.0(5) . . . . ?
C4 C5 C6 C1 0.8(5) . . . . ?
C6 C1 C2 C3 -2.5(5) . . . . ?
C6 C1 C7 O1 -141.7(3) . . . . ?
C6 C1 C7 C8 38.7(4) . . . . ?
C7 C1 C2 C3 178.8(3) . . . . ?
C7 C1 C6 C5 -179.4(3) . . . . ?
C7 C8 C9 C10 -2.3(5) . . . . ?
C7 C8 C9 C12 177.7(3) . . . . ?
C8 N1 C16 C12 1.5(3) . . . . ?
C8 N1 C16 C17 -175.8(3) . . . . ?
C8 N1 C20 C19 173.5(3) . . . . ?
C8 C9 C10 O2 -121.1(3) . . . . ?
C8 C9 C10 C11 62.8(4) . . . . ?
C8 C9 C12 Si1 -177.9(2) . . . . ?
C8 C9 C12 C16 1.5(3) . . . . ?
C9 C12 C16 N1 -1.8(3) . . . . ?
C9 C12 C16 C17 174.8(3) . . . . ?
C10 C9 C12 Si1 2.1(4) . . . . ?
C10 C9 C12 C16 -178.5(3) . . . . ?
C12 C9 C10 O2 58.9(4) . . . . ?
C12 C9 C10 C11 -117.2(3) . . . . ?
C12 C16 C17 C18 -174.9(3) . . . . ?
C13 Si1 C12 C9 42.1(3) . . . . ?
C13 Si1 C12 C16 -137.2(3) . . . . ?
C14 Si1 C12 C9 -79.7(3) . . . . ?
C14 Si1 C12 C16 101.1(3) . . . . ?
C15 Si1 C12 C9 160.7(3) . . . . ?
C15 Si1 C12 C16 -18.6(3) . . . . ?
C16 N1 C8 C7 -179.0(3) . . . . ?
C16 N1 C8 C9 -0.5(3) . . . . ?
C16 N1 C20 C19 0.1(4) . . . . ?
C16 C17 C18 C19 -0.9(5) . . . . ?
C16 C17 C18 C21 179.1(3) . . . . ?
C17 C18 C19 C20 -0.2(5) . . . . ?
C18 C19 C20 N1 0.6(5) . . . . ?
C20 N1 C8 C7 6.9(5) . . . . ?
C20 N1 C8 C9 -174.6(3) . . . . ?
C20 N1 C16 C12 176.1(2) . . . . ?
C20 N1 C16 C17 -1.2(4) . . . . ?
C21 C18 C19 C20 179.8(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.305
_oxdiff_exptl_absorpt_empirical_full_min 0.836
####################################################################### 
# 
# 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_shi_4957_elba_autored
_database_code_depnum_ccdc_archive 'CCDC 2213001'
loop_
_audit_author_name
_audit_author_address
'Sergiu shova'
;Institute of Macromolecular Chemistry, Iasi
Romania
;
_audit_update_record             
;
2022-10-14 deposited with the CCDC.	2023-01-09 downloaded from the CCDC.
;
_audit_creation_date             2022-07-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H12 Br2 N2 O'
_chemical_formula_sum            'C22 H12 Br2 N2 O'
_chemical_formula_weight         480.16
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N1O2Br1
_chemical_oxdiff_usercomment     43_FR16
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                   14.0194(10)
_cell_length_b                   7.5074(6)
_cell_length_c                   35.454(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3731.5(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2458
_cell_measurement_temperature    240.00(10)
_cell_measurement_theta_max      21.2730
_cell_measurement_theta_min      1.8680
_shelx_estimated_absorpt_T_max   0.670
_shelx_estimated_absorpt_T_min   0.355
_exptl_absorpt_coefficient_mu    4.359
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.20388
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.709
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0923
_diffrn_reflns_av_unetI/netI     0.0970
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            16286
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         1.852
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      240.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1593
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -47.00   5.00   1.00    5.00    --  -15.44 112.00 -28.00   52
  2  ω     21.00  46.00   1.00    5.00    --   17.94-112.00-121.00   25
  3  ω    -88.00 -39.00   1.00    5.00    --  -15.44-178.00   0.00   49
  4  ω     -9.00  30.00   1.00    5.00    --   17.94  77.00 150.00   39
  5  ω      2.00  82.00   1.00    5.00    --   17.94  57.00-150.00   80
  6  ω     -7.00   4.00   1.00    5.00    --   17.94  77.00-120.00   11
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0320585000
_diffrn_orient_matrix_UB_12      -0.0249054000
_diffrn_orient_matrix_UB_13      -0.0145558000
_diffrn_orient_matrix_UB_21      -0.0161630000
_diffrn_orient_matrix_UB_22      0.0893703000
_diffrn_orient_matrix_UB_23      -0.0012843000
_diffrn_orient_matrix_UB_31      0.0356205000
_diffrn_orient_matrix_UB_32      0.0180603000
_diffrn_orient_matrix_UB_33      -0.0136660000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1966
_reflns_number_total             3293
_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       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.546
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.103
_refine_ls_extinction_coef       0.00044(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1248
_refine_ls_R_factor_gt           0.0618
_refine_ls_restrained_S_all      1.063
_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)+3.0554P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0654
_refine_ls_wR_factor_ref         0.0807
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C13(H13), C14(H14), C16(H16),
 C17(H17), C18(H18), 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
Br1 Br 0.56932(5) -0.07553(10) 0.27170(2) 0.0667(3) Uani 1 1 d . . . . .
Br2 Br 0.19374(4) 0.57500(9) 0.28810(2) 0.0486(2) Uani 1 1 d . . . . .
O1 O 0.4280(3) 0.5435(5) 0.45467(11) 0.0429(11) Uani 1 1 d . . . . .
N1 N 0.6223(3) 0.6450(6) 0.44770(14) 0.0319(12) Uani 1 1 d . . . . .
N2 N 0.5888(4) 0.9784(8) 0.55992(17) 0.0667(19) Uani 1 1 d . . . . .
C1 C 0.6154(3) 0.3617(7) 0.36348(16) 0.0275(14) Uani 1 1 d . . . . .
C2 C 0.6635(4) 0.3711(8) 0.32923(18) 0.0410(17) Uani 1 1 d . . . . .
H2 H 0.706191 0.465305 0.324725 0.049 Uiso 1 1 calc R U . . .
C3 C 0.6491(4) 0.2430(8) 0.30171(19) 0.0449(18) Uani 1 1 d . . . . .
H3 H 0.681511 0.250710 0.278548 0.054 Uiso 1 1 calc R U . . .
C4 C 0.5870(4) 0.1040(8) 0.30848(16) 0.0372(16) Uani 1 1 d . . . . .
C5 C 0.5380(4) 0.0940(7) 0.34171(16) 0.0347(15) Uani 1 1 d . . . . .
H5 H 0.494900 0.000204 0.345950 0.042 Uiso 1 1 calc R U . . .
C6 C 0.5518(4) 0.2214(7) 0.36882(16) 0.0330(15) Uani 1 1 d . . . . .
H6 H 0.517654 0.213975 0.391569 0.040 Uiso 1 1 calc R U . . .
C7 C 0.6344(4) 0.4910(7) 0.39373(16) 0.0304(15) Uani 1 1 d . . . . .
C8 C 0.7262(4) 0.5418(7) 0.40491(17) 0.0343(15) Uani 1 1 d . . . . .
H8 H 0.782850 0.516152 0.391835 0.041 Uiso 1 1 calc R U . . .
C9 C 0.7198(4) 0.6359(7) 0.43825(18) 0.0347(16) Uani 1 1 d . . . . .
C10 C 0.5693(4) 0.5581(7) 0.41981(16) 0.0310(14) Uani 1 1 d . . . . .
C11 C 0.4655(4) 0.5456(7) 0.42335(17) 0.0317(15) Uani 1 1 d . . . . .
C12 C 0.4050(4) 0.5446(7) 0.38902(16) 0.0266(14) Uani 1 1 d . . . . .
C13 C 0.4344(4) 0.6116(6) 0.35459(16) 0.0295(14) Uani 1 1 d . . . . .
H13 H 0.497192 0.653273 0.351747 0.035 Uiso 1 1 calc R U . . .
C14 C 0.3727(4) 0.6180(7) 0.32444(16) 0.0302(14) Uani 1 1 d . . . . .
H14 H 0.393386 0.662463 0.301048 0.036 Uiso 1 1 calc R U . . .
C15 C 0.2805(4) 0.5588(7) 0.32881(17) 0.0354(15) Uani 1 1 d . . . . .
C16 C 0.2488(4) 0.4928(7) 0.36303(17) 0.0361(16) Uani 1 1 d . . . . .
H16 H 0.185531 0.453872 0.365931 0.043 Uiso 1 1 calc R U . . .
C17 C 0.3120(4) 0.4853(7) 0.39279(16) 0.0342(15) Uani 1 1 d . . . . .
H17 H 0.291572 0.439128 0.416065 0.041 Uiso 1 1 calc R U . . .
C18 C 0.5914(4) 0.7339(7) 0.47873(16) 0.0362(16) Uani 1 1 d . . . . .
H18 H 0.525754 0.743445 0.483757 0.043 Uiso 1 1 calc R U . . .
C19 C 0.6561(5) 0.8092(8) 0.50249(18) 0.0388(17) Uani 1 1 d . . . . .
C20 C 0.7558(5) 0.7949(8) 0.49536(19) 0.0456(18) Uani 1 1 d . . . . .
H20 H 0.800297 0.842742 0.512399 0.055 Uiso 1 1 calc R U . . .
C21 C 0.7853(4) 0.7112(7) 0.46365(19) 0.0428(17) Uani 1 1 d . . . . .
H21 H 0.850961 0.703287 0.458505 0.051 Uiso 1 1 calc R U . . .
C22 C 0.6187(5) 0.9019(9) 0.5348(2) 0.0483(19) 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
Br1 C4 1.892(6) . ?
Br2 C15 1.891(6) . ?
O1 C11 1.229(6) . ?
N1 C9 1.410(6) . ?
N1 C10 1.398(6) . ?
N1 C18 1.358(6) . ?
N2 C22 1.140(8) . ?
C1 C2 1.391(7) . ?
C1 C6 1.392(7) . ?
C1 C7 1.471(7) . ?
C2 H2 0.9400 . ?
C2 C3 1.385(7) . ?
C3 H3 0.9400 . ?
C3 C4 1.381(7) . ?
C4 C5 1.366(7) . ?
C5 H5 0.9400 . ?
C5 C6 1.370(7) . ?
C6 H6 0.9400 . ?
C7 C8 1.399(7) . ?
C7 C10 1.393(7) . ?
C8 H8 0.9400 . ?
C8 C9 1.380(7) . ?
C9 C21 1.405(7) . ?
C10 C11 1.463(7) . ?
C11 C12 1.483(7) . ?
C12 C13 1.383(7) . ?
C12 C17 1.384(7) . ?
C13 H13 0.9400 . ?
C13 C14 1.376(7) . ?
C14 H14 0.9400 . ?
C14 C15 1.376(7) . ?
C15 C16 1.384(7) . ?
C16 H16 0.9400 . ?
C16 C17 1.379(7) . ?
C17 H17 0.9400 . ?
C18 H18 0.9400 . ?
C18 C19 1.360(7) . ?
C19 C20 1.425(8) . ?
C19 C22 1.439(9) . ?
C20 H20 0.9400 . ?
C20 C21 1.353(8) . ?
C21 H21 0.9400 . ?

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
C10 N1 C9 108.9(5) . . ?
C18 N1 C9 121.7(5) . . ?
C18 N1 C10 129.3(5) . . ?
C2 C1 C6 117.9(5) . . ?
C2 C1 C7 121.0(5) . . ?
C6 C1 C7 121.1(5) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.6(6) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.6(6) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 Br1 120.1(5) . . ?
C5 C4 Br1 119.3(5) . . ?
C5 C4 C3 120.6(6) . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.7(5) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 H6 119.2 . . ?
C5 C6 C1 121.6(5) . . ?
C5 C6 H6 119.2 . . ?
C8 C7 C1 123.6(5) . . ?
C10 C7 C1 127.1(5) . . ?
C10 C7 C8 108.4(5) . . ?
C7 C8 H8 125.6 . . ?
C9 C8 C7 108.8(5) . . ?
C9 C8 H8 125.6 . . ?
C8 C9 N1 106.9(5) . . ?
C8 C9 C21 135.5(6) . . ?
C21 C9 N1 117.5(6) . . ?
N1 C10 C11 119.8(5) . . ?
C7 C10 N1 106.9(5) . . ?
C7 C10 C11 133.2(6) . . ?
O1 C11 C10 120.3(5) . . ?
O1 C11 C12 119.8(5) . . ?
C10 C11 C12 119.9(5) . . ?
C13 C12 C11 123.5(5) . . ?
C13 C12 C17 118.8(5) . . ?
C17 C12 C11 117.4(5) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.8(5) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 120.3 . . ?
C15 C14 C13 119.5(5) . . ?
C15 C14 H14 120.3 . . ?
C14 C15 Br2 119.8(5) . . ?
C14 C15 C16 121.0(6) . . ?
C16 C15 Br2 119.1(4) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 C15 118.7(5) . . ?
C17 C16 H16 120.7 . . ?
C12 C17 H17 119.4 . . ?
C16 C17 C12 121.2(5) . . ?
C16 C17 H17 119.4 . . ?
N1 C18 H18 120.2 . . ?
N1 C18 C19 119.6(6) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 C20 120.8(6) . . ?
C18 C19 C22 116.8(6) . . ?
C20 C19 C22 122.3(6) . . ?
C19 C20 H20 120.6 . . ?
C21 C20 C19 118.9(6) . . ?
C21 C20 H20 120.6 . . ?
C9 C21 H21 119.4 . . ?
C20 C21 C9 121.3(6) . . ?
C20 C21 H21 119.4 . . ?
N2 C22 C19 178.6(8) . . ?

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
Br1 C4 C5 C6 178.6(4) . . . . ?
Br2 C15 C16 C17 -178.5(4) . . . . ?
O1 C11 C12 C13 154.9(5) . . . . ?
O1 C11 C12 C17 -20.1(8) . . . . ?
N1 C9 C21 C20 -2.3(8) . . . . ?
N1 C10 C11 O1 -28.9(8) . . . . ?
N1 C10 C11 C12 148.1(5) . . . . ?
N1 C18 C19 C20 -0.4(9) . . . . ?
N1 C18 C19 C22 179.8(5) . . . . ?
C1 C2 C3 C4 -0.5(9) . . . . ?
C1 C7 C8 C9 -168.3(5) . . . . ?
C1 C7 C10 N1 167.5(5) . . . . ?
C1 C7 C10 C11 -9.1(10) . . . . ?
C2 C1 C6 C5 1.2(8) . . . . ?
C2 C1 C7 C8 -45.8(8) . . . . ?
C2 C1 C7 C10 146.2(6) . . . . ?
C2 C3 C4 Br1 -178.3(4) . . . . ?
C2 C3 C4 C5 1.6(9) . . . . ?
C3 C4 C5 C6 -1.2(9) . . . . ?
C4 C5 C6 C1 -0.3(8) . . . . ?
C6 C1 C2 C3 -0.8(8) . . . . ?
C6 C1 C7 C8 131.3(6) . . . . ?
C6 C1 C7 C10 -36.8(8) . . . . ?
C7 C1 C2 C3 176.3(5) . . . . ?
C7 C1 C6 C5 -175.9(5) . . . . ?
C7 C8 C9 N1 -0.6(6) . . . . ?
C7 C8 C9 C21 176.0(6) . . . . ?
C7 C10 C11 O1 147.4(6) . . . . ?
C7 C10 C11 C12 -35.7(9) . . . . ?
C8 C7 C10 N1 -2.0(6) . . . . ?
C8 C7 C10 C11 -178.6(6) . . . . ?
C8 C9 C21 C20 -178.5(6) . . . . ?
C9 N1 C10 C7 1.7(6) . . . . ?
C9 N1 C10 C11 178.8(5) . . . . ?
C9 N1 C18 C19 -3.3(8) . . . . ?
C10 N1 C9 C8 -0.7(6) . . . . ?
C10 N1 C9 C21 -178.0(5) . . . . ?
C10 N1 C18 C19 179.8(5) . . . . ?
C10 C7 C8 C9 1.7(6) . . . . ?
C10 C11 C12 C13 -22.0(8) . . . . ?
C10 C11 C12 C17 163.0(5) . . . . ?
C11 C12 C13 C14 -175.5(5) . . . . ?
C11 C12 C17 C16 175.0(5) . . . . ?
C12 C13 C14 C15 0.7(8) . . . . ?
C13 C12 C17 C16 -0.3(8) . . . . ?
C13 C14 C15 Br2 177.7(4) . . . . ?
C13 C14 C15 C16 -0.1(8) . . . . ?
C14 C15 C16 C17 -0.8(8) . . . . ?
C15 C16 C17 C12 0.9(8) . . . . ?
C17 C12 C13 C14 -0.6(8) . . . . ?
C18 N1 C9 C8 -178.1(5) . . . . ?
C18 N1 C9 C21 4.6(8) . . . . ?
C18 N1 C10 C7 178.9(5) . . . . ?
C18 N1 C10 C11 -4.0(9) . . . . ?
C18 C19 C20 C21 2.7(9) . . . . ?
C19 C20 C21 C9 -1.2(9) . . . . ?
C22 C19 C20 C21 -177.6(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.112
_oxdiff_exptl_absorpt_empirical_full_min 0.595
