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

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

data_2b-MCGG-BRM
_database_code_depnum_ccdc_archive 'CCDC 2075068'
loop_
_audit_author_name
_audit_author_address
'Ruben A. Toscano'
;Institute of Chemistry, UNAM
Mexico
;
_audit_update_record             
;
2021-04-02 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;
_audit_creation_date             2020-07-21
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          428-429
_chemical_formula_moiety         'C33 H23 Br2 N O, C4 H8 O'
_chemical_formula_sum            'C37 H31 Br2 N O2'
_chemical_formula_weight         681.45

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4088(7)
_cell_length_b                   12.5525(9)
_cell_length_c                   15.2532(11)
_cell_angle_alpha                71.5265(15)
_cell_angle_beta                 77.3805(15)
_cell_angle_gamma                71.2592(15)
_cell_volume                     1604.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9229
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      26.07

_exptl_crystal_description       Prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_F_000             692
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.529
_exptl_crystal_size_mid          0.341
_exptl_crystal_size_min          0.198
_exptl_absorpt_coefficient_mu    2.559
_shelx_estimated_absorpt_T_min   0.345
_shelx_estimated_absorpt_T_max   0.631
_exptl_absorpt_correction_type   Multi_scan
_exptl_absorpt_correction_T_min  0.5164
_exptl_absorpt_correction_T_max  0.7456
_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      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec ImuS'
_diffrn_radiation_monochromator  mirrors
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24786
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.778
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5863
_reflns_number_gt                4892
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0738P)²+1.3305P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5863
_refine_ls_number_parameters     428
_refine_ls_number_restraints     250
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1451
_refine_ls_wR_factor_gt          0.1378
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.41282(7) 0.82729(5) 1.02406(4) 0.1067(2) Uani 1 1 d . . . . .
Br2 Br 0.89507(6) 0.49677(5) 1.21007(3) 0.08825(19) Uani 1 1 d . . . . .
O1 O 0.5102(3) 0.6651(3) 0.89982(19) 0.0796(7) Uani 1 1 d D . . . .
H1 H 0.545(6) 0.615(4) 0.868(3) 0.119 Uiso 1 1 d D U . . .
N1 N 0.6701(3) 0.4854(3) 0.84295(18) 0.0581(7) Uani 1 1 d . . . . .
C1 C 0.7692(3) 0.2688(3) 0.54838(19) 0.0459(6) Uani 1 1 d . . . . .
C2 C 0.6642(3) 0.2265(2) 0.53343(19) 0.0449(6) Uani 1 1 d . . . . .
C3 C 0.7425(3) 0.3197(3) 0.6292(2) 0.0457(6) Uani 1 1 d . . . . .
C4 C 0.6175(4) 0.4122(3) 0.6400(2) 0.0547(7) Uani 1 1 d . . . . .
H4 H 0.546274 0.440426 0.598616 0.066 Uiso 1 1 calc R U . . .
C5 C 0.5972(4) 0.4633(3) 0.7120(2) 0.0562(7) Uani 1 1 d . . . . .
H5 H 0.512999 0.525764 0.717920 0.067 Uiso 1 1 calc R U . . .
C6 C 0.7006(4) 0.4225(3) 0.7747(2) 0.0506(7) Uani 1 1 d . . . . .
C7 C 0.8258(4) 0.3295(3) 0.7650(2) 0.0563(8) Uani 1 1 d . . . . .
H7 H 0.895770 0.300623 0.807256 0.068 Uiso 1 1 calc R U . . .
C8 C 0.8469(3) 0.2792(3) 0.6925(2) 0.0521(7) Uani 1 1 d . . . . .
H8 H 0.932097 0.217633 0.686097 0.063 Uiso 1 1 calc R U . . .
C9 C 0.9142(3) 0.2742(3) 0.4867(2) 0.0481(6) Uani 1 1 d . . . . .
C10 C 0.9604(4) 0.3759(3) 0.4589(2) 0.0579(8) Uani 1 1 d . . . . .
H10 H 0.899440 0.440389 0.479348 0.070 Uiso 1 1 calc R U . . .
C11 C 1.0946(5) 0.3838(4) 0.4015(3) 0.0740(11) Uani 1 1 d . . . . .
H11 H 1.122120 0.453279 0.383145 0.089 Uiso 1 1 calc R U . . .
C12 C 1.1863(5) 0.2900(5) 0.3721(3) 0.0823(12) Uani 1 1 d . . . . .
H12 H 1.276843 0.295081 0.333772 0.099 Uiso 1 1 calc R U . . .
C13 C 1.1450(5) 0.1878(4) 0.3991(3) 0.0867(13) Uani 1 1 d . . . . .
H13 H 1.207888 0.123536 0.379121 0.104 Uiso 1 1 calc R U . . .
C14 C 1.0094(4) 0.1796(3) 0.4564(3) 0.0690(9) Uani 1 1 d . . . . .
H14 H 0.982716 0.109856 0.474292 0.083 Uiso 1 1 calc R U . . .
C15 C 0.5295(3) 0.2111(3) 0.6040(2) 0.0480(7) Uani 1 1 d . . . . .
C16 C 0.3841(4) 0.2659(3) 0.5793(3) 0.0632(8) Uani 1 1 d . . . . .
H16 H 0.371803 0.311036 0.518587 0.076 Uiso 1 1 calc R U . . .
C17 C 0.2581(4) 0.2541(4) 0.6439(3) 0.0805(11) Uani 1 1 d . . . . .
H17 H 0.161766 0.293472 0.627125 0.097 Uiso 1 1 calc R U . . .
C18 C 0.2748(5) 0.1848(4) 0.7323(3) 0.0785(11) Uani 1 1 d . . . . .
H18 H 0.189690 0.175896 0.775249 0.094 Uiso 1 1 calc R U . . .
C19 C 0.4173(5) 0.1280(4) 0.7582(2) 0.0722(10) Uani 1 1 d . . . . .
H19 H 0.428620 0.080464 0.818442 0.087 Uiso 1 1 calc R U . . .
C20 C 0.5445(4) 0.1423(3) 0.6933(2) 0.0598(8) Uani 1 1 d . . . . .
H20 H 0.640644 0.104596 0.710916 0.072 Uiso 1 1 calc DR U . . .
C21 C 0.6685(3) 0.1954(3) 0.4462(2) 0.0461(6) Uani 1 1 d . . . . .
C22 C 0.6960(4) 0.2689(3) 0.3593(2) 0.0542(7) Uani 1 1 d . . . . .
H22 H 0.719026 0.337307 0.354888 0.065 Uiso 1 1 calc R U . . .
C23 C 0.6903(5) 0.2432(3) 0.2791(2) 0.0675(9) Uani 1 1 d . . . . .
H23 H 0.708645 0.294323 0.221259 0.081 Uiso 1 1 calc R U . . .
C24 C 0.6574(5) 0.1421(4) 0.2842(3) 0.0729(10) Uani 1 1 d . . . . .
H24 H 0.652430 0.125005 0.230123 0.087 Uiso 1 1 calc R U . . .
C25 C 0.6320(5) 0.0670(4) 0.3693(3) 0.0778(11) Uani 1 1 d . . . . .
H25 H 0.612049 -0.002282 0.372966 0.093 Uiso 1 1 calc R U . . .
C26 C 0.6358(4) 0.0934(3) 0.4502(2) 0.0636(9) Uani 1 1 d . . . . .
H26 H 0.616358 0.042329 0.507759 0.076 Uiso 1 1 calc R U . . .
C27 C 0.7467(4) 0.4513(3) 0.9112(2) 0.0602(8) Uani 1 1 d . . . . .
H27 H 0.823273 0.381593 0.918877 0.072 Uiso 1 1 calc R U . . .
C28 C 0.7144(4) 0.5212(3) 0.9772(2) 0.0576(8) Uani 1 1 d . . . . .
C29 C 0.5975(4) 0.6246(3) 0.9683(2) 0.0627(8) Uani 1 1 d . . . . .
C30 C 0.5702(5) 0.6877(4) 1.0342(2) 0.0694(9) Uani 1 1 d . . . . .
C31 C 0.6570(5) 0.6492(4) 1.1062(2) 0.0719(10) Uani 1 1 d . . . . .
H31 H 0.637011 0.690917 1.150174 0.086 Uiso 1 1 calc R U . . .
C32 C 0.7730(5) 0.5484(4) 1.1120(2) 0.0660(9) Uani 1 1 d . . . . .
C33 C 0.8039(4) 0.4830(3) 1.0493(2) 0.0631(8) Uani 1 1 d . . . . .
H33 H 0.882632 0.414642 1.054802 0.076 Uiso 1 1 calc R U . . .
O2 O 0.9434(16) 0.7738(10) 0.9457(10) 0.205(3) Uani 0.560(8) 1 d D U P A 1
C34 C 0.876(3) 0.8170(16) 0.8674(13) 0.204(3) Uani 0.560(8) 1 d D U P A 1
H34A H 0.767097 0.828415 0.883587 0.245 Uiso 0.560(8) 1 calc R U P A 1
H34B H 0.913442 0.762419 0.829207 0.245 Uiso 0.560(8) 1 calc R U P A 1
C35 C 0.9076(18) 0.9271(13) 0.8164(11) 0.205(3) Uani 0.560(8) 1 d D U P A 1
H35A H 0.816148 0.984688 0.795255 0.246 Uiso 0.560(8) 1 calc R U P A 1
H35B H 0.982027 0.917651 0.762268 0.246 Uiso 0.560(8) 1 calc R U P A 1
C36 C 0.968(3) 0.9660(14) 0.8810(14) 0.205(3) Uani 0.560(8) 1 d D U P A 1
H36A H 1.066914 0.977735 0.854993 0.245 Uiso 0.560(8) 1 calc R U P A 1
H36B H 0.899866 1.038111 0.892775 0.245 Uiso 0.560(8) 1 calc R U P A 1
C37 C 0.976(3) 0.8688(16) 0.9677(12) 0.205(3) Uani 0.560(8) 1 d D U P A 1
H37A H 1.076089 0.843352 0.986857 0.246 Uiso 0.560(8) 1 calc R U P A 1
H37B H 0.902233 0.893574 1.017755 0.246 Uiso 0.560(8) 1 calc R U P A 1
O2A O 0.978(2) 0.8279(15) 0.9891(11) 0.205(3) Uani 0.440(8) 1 d D U P A 2
C34A C 0.827(2) 0.856(2) 0.9832(13) 0.205(3) Uani 0.440(8) 1 d D U P A 2
H34C H 0.772341 0.919873 1.011162 0.246 Uiso 0.440(8) 1 calc R U P A 2
H34D H 0.787730 0.789630 1.015448 0.246 Uiso 0.440(8) 1 calc R U P A 2
C35A C 0.812(2) 0.891(2) 0.8841(16) 0.205(3) Uani 0.440(8) 1 d D U P A 2
H35C H 0.714374 0.946539 0.872263 0.246 Uiso 0.440(8) 1 calc R U P A 2
H35D H 0.821874 0.824020 0.862644 0.246 Uiso 0.440(8) 1 calc R U P A 2
C36A C 0.938(3) 0.947(2) 0.8360(14) 0.205(3) Uani 0.440(8) 1 d D U P A 2
H36C H 0.982666 0.925687 0.778107 0.246 Uiso 0.440(8) 1 calc R U P A 2
H36D H 0.902043 1.031260 0.822766 0.246 Uiso 0.440(8) 1 calc R U P A 2
C37A C 1.049(2) 0.898(2) 0.9049(16) 0.205(3) Uani 0.440(8) 1 d D U P A 2
H37C H 1.142598 0.850154 0.880197 0.246 Uiso 0.440(8) 1 calc R U P A 2
H37D H 1.071145 0.960902 0.919020 0.246 Uiso 0.440(8) 1 calc R U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C30 1.883(4) . ?
Br2 C32 1.907(3) . ?
O1 C29 1.339(4) . ?
O1 H1 0.86(2) . ?
N1 C27 1.278(4) . ?
N1 C6 1.427(4) . ?
C1 C2 1.350(4) . ?
C1 C9 1.486(4) . ?
C1 C3 1.500(4) . ?
C2 C21 1.491(4) . ?
C2 C15 1.494(4) . ?
C3 C4 1.385(4) . ?
C3 C8 1.392(4) . ?
C4 C5 1.389(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.386(5) . ?
C7 C8 1.388(4) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C14 1.383(5) . ?
C9 C10 1.389(4) . ?
C10 C11 1.383(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.358(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.372(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.392(6) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C20 1.372(4) . ?
C15 C16 1.393(5) . ?
C16 C17 1.382(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.364(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.379(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.397(5) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.379(4) . ?
C21 C26 1.390(4) . ?
C22 C23 1.377(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.375(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.365(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.385(5) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 C28 1.460(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.396(5) . ?
C28 C33 1.400(5) . ?
C29 C30 1.402(5) . ?
C30 C31 1.381(5) . ?
C31 C32 1.372(6) . ?
C31 H31 0.9300 . ?
C32 C33 1.377(5) . ?
C33 H33 0.9300 . ?
O2 C34 1.352(13) . ?
O2 C37 1.471(13) . ?
C34 C35 1.446(14) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 C36 1.501(14) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 C37 1.485(13) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
O2A C34A 1.363(15) . ?
O2A C37A 1.469(15) . ?
C34A C35A 1.461(16) . ?
C34A H34C 0.9700 . ?
C34A H34D 0.9700 . ?
C35A C36A 1.502(16) . ?
C35A H35C 0.9700 . ?
C35A H35D 0.9700 . ?
C36A C37A 1.494(15) . ?
C36A H36C 0.9700 . ?
C36A H36D 0.9700 . ?
C37A H37C 0.9700 . ?
C37A H37D 0.9700 . ?

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
C29 O1 H1 104(4) . . ?
C27 N1 C6 122.5(3) . . ?
C2 C1 C9 124.5(3) . . ?
C2 C1 C3 120.8(3) . . ?
C9 C1 C3 114.6(2) . . ?
C1 C2 C21 124.0(3) . . ?
C1 C2 C15 121.4(2) . . ?
C21 C2 C15 114.5(2) . . ?
C4 C3 C8 118.2(3) . . ?
C4 C3 C1 120.9(3) . . ?
C8 C3 C1 120.8(3) . . ?
C3 C4 C5 120.9(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 120.6(3) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 119.1(3) . . ?
C5 C6 N1 115.2(3) . . ?
C7 C6 N1 125.6(3) . . ?
C6 C7 C8 120.2(3) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C7 C8 C3 121.0(3) . . ?
C7 C8 H8 119.5 . . ?
C3 C8 H8 119.5 . . ?
C14 C9 C10 117.3(3) . . ?
C14 C9 C1 122.3(3) . . ?
C10 C9 C1 120.3(3) . . ?
C11 C10 C9 121.7(3) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C12 C11 C10 120.0(4) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 119.8(4) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C14 120.5(4) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C9 C14 C13 120.7(4) . . ?
C9 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C20 C15 C16 118.4(3) . . ?
C20 C15 C2 121.6(3) . . ?
C16 C15 C2 120.0(3) . . ?
C17 C16 C15 120.9(4) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C18 C17 C16 120.1(4) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.3(4) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C20 119.4(4) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C15 C20 C19 120.9(3) . . ?
C15 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C22 C21 C26 117.7(3) . . ?
C22 C21 C2 121.7(3) . . ?
C26 C21 C2 120.5(3) . . ?
C23 C22 C21 121.5(3) . . ?
C23 C22 H22 119.3 . . ?
C21 C22 H22 119.3 . . ?
C24 C23 C22 120.1(3) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C25 C24 C23 119.6(3) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C24 C25 C26 120.4(3) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C21 120.7(3) . . ?
C25 C26 H26 119.6 . . ?
C21 C26 H26 119.6 . . ?
N1 C27 C28 120.3(3) . . ?
N1 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
C29 C28 C33 120.6(3) . . ?
C29 C28 C27 120.8(3) . . ?
C33 C28 C27 118.6(3) . . ?
O1 C29 C28 122.6(3) . . ?
O1 C29 C30 119.0(4) . . ?
C28 C29 C30 118.5(3) . . ?
C31 C30 C29 121.0(4) . . ?
C31 C30 Br1 119.6(3) . . ?
C29 C30 Br1 119.4(3) . . ?
C32 C31 C30 119.2(3) . . ?
C32 C31 H31 120.4 . . ?
C30 C31 H31 120.4 . . ?
C31 C32 C33 122.1(3) . . ?
C31 C32 Br2 119.1(3) . . ?
C33 C32 Br2 118.8(3) . . ?
C32 C33 C28 118.7(4) . . ?
C32 C33 H33 120.6 . . ?
C28 C33 H33 120.6 . . ?
C34 O2 C37 109.5(9) . . ?
O2 C34 C35 108.7(9) . . ?
O2 C34 H34A 109.9 . . ?
C35 C34 H34A 109.9 . . ?
O2 C34 H34B 109.9 . . ?
C35 C34 H34B 109.9 . . ?
H34A C34 H34B 108.3 . . ?
C34 C35 C36 107.6(9) . . ?
C34 C35 H35A 110.2 . . ?
C36 C35 H35A 110.2 . . ?
C34 C35 H35B 110.2 . . ?
C36 C35 H35B 110.2 . . ?
H35A C35 H35B 108.5 . . ?
C37 C36 C35 104.2(9) . . ?
C37 C36 H36A 110.9 . . ?
C35 C36 H36A 110.9 . . ?
C37 C36 H36B 110.9 . . ?
C35 C36 H36B 110.9 . . ?
H36A C36 H36B 108.9 . . ?
O2 C37 C36 106.2(9) . . ?
O2 C37 H37A 110.5 . . ?
C36 C37 H37A 110.5 . . ?
O2 C37 H37B 110.5 . . ?
C36 C37 H37B 110.5 . . ?
H37A C37 H37B 108.7 . . ?
C34A O2A C37A 108.2(10) . . ?
O2A C34A C35A 106.6(11) . . ?
O2A C34A H34C 110.4 . . ?
C35A C34A H34C 110.4 . . ?
O2A C34A H34D 110.4 . . ?
C35A C34A H34D 110.4 . . ?
H34C C34A H34D 108.6 . . ?
C34A C35A C36A 105.2(11) . . ?
C34A C35A H35C 110.7 . . ?
C36A C35A H35C 110.7 . . ?
C34A C35A H35D 110.7 . . ?
C36A C35A H35D 110.7 . . ?
H35C C35A H35D 108.8 . . ?
C37A C36A C35A 103.4(10) . . ?
C37A C36A H36C 111.1 . . ?
C35A C36A H36C 111.1 . . ?
C37A C36A H36D 111.1 . . ?
C35A C36A H36D 111.1 . . ?
H36C C36A H36D 109.0 . . ?
O2A C37A C36A 106.6(10) . . ?
O2A C37A H37C 110.4 . . ?
C36A C37A H37C 110.4 . . ?
O2A C37A H37D 110.4 . . ?
C36A C37A H37D 110.4 . . ?
H37C C37A H37D 108.6 . . ?

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
C9 C1 C2 C21 -9.2(5) . . . . ?
C3 C1 C2 C21 168.1(3) . . . . ?
C9 C1 C2 C15 172.9(3) . . . . ?
C3 C1 C2 C15 -9.8(4) . . . . ?
C2 C1 C3 C4 -57.3(4) . . . . ?
C9 C1 C3 C4 120.2(3) . . . . ?
C2 C1 C3 C8 126.1(3) . . . . ?
C9 C1 C3 C8 -56.3(4) . . . . ?
C8 C3 C4 C5 0.2(5) . . . . ?
C1 C3 C4 C5 -176.5(3) . . . . ?
C3 C4 C5 C6 -0.5(5) . . . . ?
C4 C5 C6 C7 0.1(5) . . . . ?
C4 C5 C6 N1 177.6(3) . . . . ?
C27 N1 C6 C5 172.8(3) . . . . ?
C27 N1 C6 C7 -9.9(5) . . . . ?
C5 C6 C7 C8 0.6(5) . . . . ?
N1 C6 C7 C8 -176.6(3) . . . . ?
C6 C7 C8 C3 -1.0(5) . . . . ?
C4 C3 C8 C7 0.6(5) . . . . ?
C1 C3 C8 C7 177.2(3) . . . . ?
C2 C1 C9 C14 -48.7(4) . . . . ?
C3 C1 C9 C14 133.8(3) . . . . ?
C2 C1 C9 C10 132.6(3) . . . . ?
C3 C1 C9 C10 -44.8(4) . . . . ?
C14 C9 C10 C11 1.3(5) . . . . ?
C1 C9 C10 C11 -180.0(3) . . . . ?
C9 C10 C11 C12 -1.0(5) . . . . ?
C10 C11 C12 C13 0.3(6) . . . . ?
C11 C12 C13 C14 0.2(7) . . . . ?
C10 C9 C14 C13 -0.8(5) . . . . ?
C1 C9 C14 C13 -179.5(3) . . . . ?
C12 C13 C14 C9 0.1(6) . . . . ?
C1 C2 C15 C20 -57.9(4) . . . . ?
C21 C2 C15 C20 124.0(3) . . . . ?
C1 C2 C15 C16 123.1(3) . . . . ?
C21 C2 C15 C16 -54.9(4) . . . . ?
C20 C15 C16 C17 1.9(5) . . . . ?
C2 C15 C16 C17 -179.1(3) . . . . ?
C15 C16 C17 C18 -2.4(6) . . . . ?
C16 C17 C18 C19 1.2(6) . . . . ?
C17 C18 C19 C20 0.3(6) . . . . ?
C16 C15 C20 C19 -0.4(5) . . . . ?
C2 C15 C20 C19 -179.4(3) . . . . ?
C18 C19 C20 C15 -0.7(5) . . . . ?
C1 C2 C21 C22 -46.8(4) . . . . ?
C15 C2 C21 C22 131.2(3) . . . . ?
C1 C2 C21 C26 137.0(3) . . . . ?
C15 C2 C21 C26 -45.0(4) . . . . ?
C26 C21 C22 C23 0.6(5) . . . . ?
C2 C21 C22 C23 -175.8(3) . . . . ?
C21 C22 C23 C24 -0.4(6) . . . . ?
C22 C23 C24 C25 -0.6(6) . . . . ?
C23 C24 C25 C26 1.5(7) . . . . ?
C24 C25 C26 C21 -1.3(7) . . . . ?
C22 C21 C26 C25 0.3(5) . . . . ?
C2 C21 C26 C25 176.7(3) . . . . ?
C6 N1 C27 C28 177.7(3) . . . . ?
N1 C27 C28 C29 1.6(5) . . . . ?
N1 C27 C28 C33 -178.0(3) . . . . ?
C33 C28 C29 O1 179.2(3) . . . . ?
C27 C28 C29 O1 -0.3(5) . . . . ?
C33 C28 C29 C30 -1.1(5) . . . . ?
C27 C28 C29 C30 179.3(3) . . . . ?
O1 C29 C30 C31 179.8(3) . . . . ?
C28 C29 C30 C31 0.2(5) . . . . ?
O1 C29 C30 Br1 -0.2(5) . . . . ?
C28 C29 C30 Br1 -179.8(3) . . . . ?
C29 C30 C31 C32 1.1(6) . . . . ?
Br1 C30 C31 C32 -178.9(3) . . . . ?
C30 C31 C32 C33 -1.4(5) . . . . ?
C30 C31 C32 Br2 178.9(3) . . . . ?
C31 C32 C33 C28 0.5(5) . . . . ?
Br2 C32 C33 C28 -179.8(2) . . . . ?
C29 C28 C33 C32 0.8(5) . . . . ?
C27 C28 C33 C32 -179.6(3) . . . . ?
C37 O2 C34 C35 20(2) . . . . ?
O2 C34 C35 C36 -15(2) . . . . ?
C34 C35 C36 C37 3(2) . . . . ?
C34 O2 C37 C36 -18(2) . . . . ?
C35 C36 C37 O2 8(2) . . . . ?
C37A O2A C34A C35A 30(2) . . . . ?
O2A C34A C35A C36A -32(2) . . . . ?
C34A C35A C36A C37A 22(3) . . . . ?
C34A O2A C37A C36A -15(3) . . . . ?
C35A C36A C37A O2A -5(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
O1 H1 N1 0.86(2) 1.77(3) 2.568(4) 153(6) . yes

_refine_diff_density_max         1.169
_refine_diff_density_min         -0.885
_refine_diff_density_rms         0.059

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_4c-MCGG-BRM
_database_code_depnum_ccdc_archive 'CCDC 2075072'
loop_
_audit_author_name
_audit_author_address
'Ruben A. Toscano'
;Institute of Chemistry, UNAM
Mexico
;
_audit_update_record             
;
2021-04-02 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;
_audit_creation_date             2020-07-21
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          511-513
_chemical_formula_moiety         'C45 H32 B I2 N O'
_chemical_formula_sum            'C45 H32 B I2 N O'
_chemical_formula_weight         867.32

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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.864(4)
_cell_length_b                   12.004(4)
_cell_length_c                   14.739(5)
_cell_angle_alpha                99.378(10)
_cell_angle_beta                 91.705(10)
_cell_angle_gamma                91.595(10)
_cell_volume                     1894.5(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9333
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      29.83

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.385
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.067
_exptl_absorpt_coefficient_mu    1.695
_shelx_estimated_absorpt_T_min   0.561
_shelx_estimated_absorpt_T_max   0.895
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5557
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus X-ray source'
_diffrn_radiation_monochromator  'Helios multilayer mirror'
_diffrn_measurement_device_type  
'Bruker D8 Venture κ geometry diffractometer 208039-1'
_diffrn_measurement_method       'φ and ω-scans'
_diffrn_detector_area_resol_mean 52.0833
_diffrn_reflns_number            47545
_diffrn_reflns_av_unetI/netI     0.0615
_diffrn_reflns_av_R_equivalents  0.0709
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.303
_diffrn_reflns_theta_max         29.575
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             10586
_reflns_number_gt                5813
_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 v2018.1-0(Bruker, 2018)'
_computing_cell_refinement       'APEX3 v2018.1-0(Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2014)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXLe (HÃ1/4bschle et al, 2011)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_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)+(0.0722P)²+1.0002P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10586
_refine_ls_number_parameters     451
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1126
_refine_ls_R_factor_gt           0.0557
_refine_ls_wR_factor_ref         0.1629
_refine_ls_wR_factor_gt          0.1352
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.71195(3) 0.39780(3) 0.91355(2) 0.06714(14) Uani 1 1 d . . . . .
I2 I 0.47214(4) 0.84726(3) 0.95403(3) 0.08684(16) Uani 1 1 d . . . . .
O1 O 0.5529(3) 0.3747(2) 0.7258(2) 0.0506(7) Uani 1 1 d . . . . .
B2 B 0.4730(4) 0.3152(4) 0.6461(3) 0.0452(10) Uani 1 1 d . . . . .
N3 N 0.3953(3) 0.4169(3) 0.6089(2) 0.0390(7) Uani 1 1 d . . . . .
C4 C 0.3908(3) 0.5165(3) 0.6562(3) 0.0430(9) Uani 1 1 d . . . . .
H4 H 0.341581 0.570291 0.632875 0.052 Uiso 1 1 calc R U . . .
C5 C 0.4403(4) 0.6588(3) 0.7919(3) 0.0511(10) Uani 1 1 d . . . . .
H5 H 0.388911 0.710508 0.767780 0.061 Uiso 1 1 calc R U . . .
C6 C 0.5012(4) 0.6886(3) 0.8766(3) 0.0547(11) Uani 1 1 d . . . . .
C7 C 0.5768(4) 0.6149(4) 0.9105(3) 0.0555(11) Uani 1 1 d . . . . .
H7 H 0.617561 0.636732 0.968845 0.067 Uiso 1 1 calc R U . . .
C8 C 0.5949(4) 0.5088(4) 0.8608(3) 0.0486(10) Uani 1 1 d . . . . .
C9 C 0.5341(3) 0.4738(3) 0.7748(3) 0.0424(9) Uani 1 1 d . . . . .
C10 C 0.4564(3) 0.5502(3) 0.7424(3) 0.0429(9) Uani 1 1 d . . . . .
C11 C 0.3178(3) 0.3942(3) 0.5263(3) 0.0380(8) Uani 1 1 d . . . . .
C12 C 0.1929(3) 0.4113(3) 0.5322(3) 0.0428(9) Uani 1 1 d . . . . .
H12 H 0.158485 0.437232 0.590012 0.051 Uiso 1 1 calc R U . . .
C13 C 0.1184(3) 0.3903(3) 0.4530(3) 0.0459(9) Uani 1 1 d . . . . .
H13 H 0.032707 0.403065 0.457191 0.055 Uiso 1 1 calc R U . . .
C14 C 0.1657(3) 0.3510(3) 0.3680(3) 0.0411(8) Uani 1 1 d . . . . .
C15 C 0.2920(3) 0.3354(3) 0.3641(3) 0.0417(9) Uani 1 1 d . . . . .
H15 H 0.326738 0.309468 0.306405 0.050 Uiso 1 1 calc R U . . .
C16 C 0.3685(3) 0.3567(3) 0.4423(3) 0.0431(9) Uani 1 1 d . . . . .
H16 H 0.454540 0.345691 0.438296 0.052 Uiso 1 1 calc R U . . .
C17 C 0.0879(3) 0.3310(4) 0.2817(3) 0.0446(9) Uani 1 1 d . . . . .
C18 C 0.0893(4) 0.2314(3) 0.2243(3) 0.0452(9) Uani 1 1 d . . . . .
C19 C 0.0181(4) 0.4291(3) 0.2626(3) 0.0445(9) Uani 1 1 d . . . . .
C20 C 0.0695(4) 0.5381(4) 0.2854(3) 0.0571(11) Uani 1 1 d . . . . .
H20 H 0.149127 0.548635 0.314501 0.069 Uiso 1 1 calc R U . . .
C21 C 0.0081(5) 0.6308(4) 0.2669(4) 0.0695(13) Uani 1 1 d . . . . .
H21 H 0.045328 0.704102 0.283563 0.083 Uiso 1 1 calc R U . . .
C22 C -0.1061(5) 0.6180(5) 0.2248(3) 0.0686(14) Uani 1 1 d . . . . .
H22 H -0.148559 0.681771 0.211354 0.082 Uiso 1 1 calc R U . . .
C23 C -0.1586(4) 0.5118(5) 0.2023(3) 0.0636(13) Uani 1 1 d . . . . .
H23 H -0.237930 0.502515 0.172734 0.076 Uiso 1 1 calc R U . . .
C24 C -0.1000(4) 0.4188(4) 0.2213(3) 0.0532(10) Uani 1 1 d . . . . .
H24 H -0.139861 0.346416 0.206277 0.064 Uiso 1 1 calc R U . . .
C25 C 0.0384(4) 0.2173(3) 0.1277(3) 0.0478(10) Uani 1 1 d . . . . .
C26 C 0.0747(5) 0.2904(5) 0.0694(3) 0.0696(13) Uani 1 1 d . . . . .
H26 H 0.133339 0.349771 0.090891 0.084 Uiso 1 1 calc R U . . .
C27 C 0.0280(7) 0.2787(7) -0.0180(4) 0.098(2) Uani 1 1 d . . . . .
H27 H 0.052516 0.331495 -0.056088 0.117 Uiso 1 1 calc R U . . .
C28 C -0.0531(7) 0.1931(7) -0.0522(4) 0.099(2) Uani 1 1 d . . . . .
H28 H -0.082587 0.183857 -0.114405 0.119 Uiso 1 1 calc R U . . .
C29 C -0.0914(6) 0.1211(6) 0.0037(5) 0.097(2) Uani 1 1 d . . . . .
H29 H -0.150781 0.062834 -0.018999 0.116 Uiso 1 1 calc R U . . .
C30 C -0.0455(5) 0.1307(4) 0.0937(4) 0.0711(14) Uani 1 1 d . . . . .
H30 H -0.071534 0.078270 0.131603 0.085 Uiso 1 1 calc R U . . .
C31 C 0.1479(4) 0.1302(4) 0.2512(3) 0.0532(11) Uani 1 1 d . . . . .
C32 C 0.2362(5) 0.0749(4) 0.1971(4) 0.0718(14) Uani 1 1 d . . . . .
H32 H 0.257426 0.100974 0.141876 0.086 Uiso 1 1 calc R U . . .
C33 C 0.2946(7) -0.0178(6) 0.2213(5) 0.099(2) Uani 1 1 d . . . . .
H33 H 0.356414 -0.054201 0.184083 0.119 Uiso 1 1 calc R U . . .
C34 C 0.2614(8) -0.0551(6) 0.2993(7) 0.114(3) Uani 1 1 d . . . . .
H34 H 0.299619 -0.119533 0.315822 0.136 Uiso 1 1 calc R U . . .
C35 C 0.1747(7) -0.0029(6) 0.3548(5) 0.102(2) Uani 1 1 d . . . . .
H35 H 0.154206 -0.030089 0.409699 0.122 Uiso 1 1 calc R U . . .
C36 C 0.1162(5) 0.0907(4) 0.3307(4) 0.0746(14) Uani 1 1 d . . . . .
H36 H 0.054991 0.126924 0.368639 0.089 Uiso 1 1 calc R U . . .
C37 C 0.3746(4) 0.2308(3) 0.6811(3) 0.0489(10) Uani 1 1 d . . . . .
C38 C 0.2747(4) 0.1784(4) 0.6255(3) 0.0550(11) Uani 1 1 d . . . . .
H38 H 0.265561 0.192082 0.564026 0.066 Uiso 1 1 calc R U . . .
C39 C 0.1905(5) 0.1083(4) 0.6573(4) 0.0692(14) Uani 1 1 d . . . . .
H39 H 0.122899 0.076110 0.618532 0.083 Uiso 1 1 calc R U . . .
C40 C 0.2036(6) 0.0846(5) 0.7448(5) 0.0831(17) Uani 1 1 d . . . . .
H40 H 0.145489 0.035534 0.766584 0.100 Uiso 1 1 calc R U . . .
C41 C 0.3004(7) 0.1317(6) 0.8006(5) 0.0921(19) Uani 1 1 d . . . . .
H41 H 0.309813 0.114860 0.861127 0.111 Uiso 1 1 calc R U . . .
C42 C 0.3846(5) 0.2038(4) 0.7694(4) 0.0685(13) Uani 1 1 d . . . . .
H42 H 0.451152 0.235976 0.809225 0.082 Uiso 1 1 calc R U . . .
C43 C 0.5629(3) 0.2620(3) 0.5667(3) 0.0452(9) Uani 1 1 d . . . . .
C44 C 0.6701(4) 0.3210(4) 0.5509(4) 0.0578(12) Uani 1 1 d . . . . .
H44 H 0.690885 0.390990 0.589263 0.069 Uiso 1 1 calc R U . . .
C45 C 0.7471(5) 0.2807(5) 0.4811(5) 0.0773(16) Uani 1 1 d . . . . .
H45 H 0.820192 0.322904 0.473080 0.093 Uiso 1 1 calc R U . . .
C46 C 0.7205(5) 0.1816(4) 0.4234(4) 0.0785(16) Uani 1 1 d . . . . .
H46 H 0.773349 0.155183 0.374842 0.094 Uiso 1 1 calc R U . . .
C47 C 0.6159(5) 0.1211(4) 0.4369(4) 0.0737(15) Uani 1 1 d . . . . .
H47 H 0.595633 0.051928 0.397238 0.088 Uiso 1 1 calc R U . . .
C48 C 0.5382(4) 0.1604(4) 0.5088(3) 0.0590(12) Uani 1 1 d . . . . .
H48 H 0.467069 0.116275 0.518031 0.071 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
I1 C8 2.091(4) . ?
I2 C6 2.092(4) . ?
O1 C9 1.312(5) . ?
O1 B2 1.508(5) . ?
B2 C37 1.607(6) . ?
B2 C43 1.609(7) . ?
B2 N3 1.659(6) . ?
N3 C4 1.285(5) . ?
N3 C11 1.444(4) . ?
C4 C10 1.431(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(6) . ?
C5 C10 1.404(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.366(7) . ?
C7 C8 1.384(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.407(5) . ?
C9 C10 1.394(6) . ?
C11 C12 1.381(5) . ?
C11 C16 1.382(5) . ?
C12 C13 1.384(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.392(5) . ?
C14 C17 1.488(5) . ?
C15 C16 1.385(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.349(6) . ?
C17 C19 1.479(6) . ?
C18 C31 1.491(6) . ?
C18 C25 1.493(5) . ?
C19 C20 1.394(6) . ?
C19 C24 1.397(6) . ?
C20 C21 1.372(7) . ?
C20 H20 0.9500 . ?
C21 C22 1.364(8) . ?
C21 H21 0.9500 . ?
C22 C23 1.368(7) . ?
C22 H22 0.9500 . ?
C23 C24 1.363(7) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C26 1.383(7) . ?
C25 C30 1.383(6) . ?
C26 C27 1.354(8) . ?
C26 H26 0.9500 . ?
C27 C28 1.357(10) . ?
C27 H27 0.9500 . ?
C28 C29 1.354(10) . ?
C28 H28 0.9500 . ?
C29 C30 1.388(8) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C32 1.381(7) . ?
C31 C36 1.384(7) . ?
C32 C33 1.387(8) . ?
C32 H32 0.9500 . ?
C33 C34 1.356(11) . ?
C33 H33 0.9500 . ?
C34 C35 1.365(11) . ?
C34 H34 0.9500 . ?
C35 C36 1.396(9) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 C42 1.392(7) . ?
C37 C38 1.409(6) . ?
C38 C39 1.369(6) . ?
C38 H38 0.9500 . ?
C39 C40 1.369(8) . ?
C39 H39 0.9500 . ?
C40 C41 1.366(9) . ?
C40 H40 0.9500 . ?
C41 C42 1.381(8) . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?
C43 C48 1.385(6) . ?
C43 C44 1.392(6) . ?
C44 C45 1.380(7) . ?
C44 H44 0.9500 . ?
C45 C46 1.364(7) . ?
C45 H45 0.9500 . ?
C46 C47 1.369(7) . ?
C46 H46 0.9500 . ?
C47 C48 1.405(7) . ?
C47 H47 0.9500 . ?
C48 H48 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
C9 O1 B2 126.4(3) . . ?
O1 B2 C37 110.3(4) . . ?
O1 B2 C43 107.5(3) . . ?
C37 B2 C43 117.3(3) . . ?
O1 B2 N3 104.9(3) . . ?
C37 B2 N3 107.5(3) . . ?
C43 B2 N3 108.6(3) . . ?
C4 N3 C11 116.4(3) . . ?
C4 N3 B2 122.1(3) . . ?
C11 N3 B2 121.2(3) . . ?
N3 C4 C10 123.2(4) . . ?
N3 C4 H4 118.4 . . ?
C10 C4 H4 118.4 . . ?
C6 C5 C10 118.4(4) . . ?
C6 C5 H5 120.8 . . ?
C10 C5 H5 120.8 . . ?
C7 C6 C5 120.8(4) . . ?
C7 C6 I2 120.2(3) . . ?
C5 C6 I2 118.9(4) . . ?
C6 C7 C8 120.8(4) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C7 C8 C9 120.6(4) . . ?
C7 C8 I1 120.2(3) . . ?
C9 C8 I1 119.2(3) . . ?
O1 C9 C10 121.3(3) . . ?
O1 C9 C8 121.3(4) . . ?
C10 C9 C8 117.3(4) . . ?
C9 C10 C5 122.0(4) . . ?
C9 C10 C4 118.9(3) . . ?
C5 C10 C4 119.1(4) . . ?
C12 C11 C16 120.6(3) . . ?
C12 C11 N3 119.2(3) . . ?
C16 C11 N3 120.2(3) . . ?
C11 C12 C13 119.4(4) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C12 C13 C14 121.6(4) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C13 C14 C15 117.7(3) . . ?
C13 C14 C17 122.5(3) . . ?
C15 C14 C17 119.8(3) . . ?
C16 C15 C14 121.7(4) . . ?
C16 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
C11 C16 C15 119.1(3) . . ?
C11 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C18 C17 C19 124.1(4) . . ?
C18 C17 C14 120.6(4) . . ?
C19 C17 C14 115.2(3) . . ?
C17 C18 C31 122.2(4) . . ?
C17 C18 C25 122.0(4) . . ?
C31 C18 C25 115.7(3) . . ?
C20 C19 C24 116.7(4) . . ?
C20 C19 C17 120.3(4) . . ?
C24 C19 C17 123.0(4) . . ?
C21 C20 C19 121.7(4) . . ?
C21 C20 H20 119.1 . . ?
C19 C20 H20 119.1 . . ?
C22 C21 C20 120.3(5) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C23 118.9(5) . . ?
C21 C22 H22 120.5 . . ?
C23 C22 H22 120.5 . . ?
C24 C23 C22 121.8(4) . . ?
C24 C23 H23 119.1 . . ?
C22 C23 H23 119.1 . . ?
C23 C24 C19 120.6(4) . . ?
C23 C24 H24 119.7 . . ?
C19 C24 H24 119.7 . . ?
C26 C25 C30 118.0(4) . . ?
C26 C25 C18 120.7(4) . . ?
C30 C25 C18 121.2(4) . . ?
C27 C26 C25 121.0(6) . . ?
C27 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
C26 C27 C28 121.3(7) . . ?
C26 C27 H27 119.4 . . ?
C28 C27 H27 119.4 . . ?
C29 C28 C27 118.9(5) . . ?
C29 C28 H28 120.5 . . ?
C27 C28 H28 120.5 . . ?
C28 C29 C30 121.2(6) . . ?
C28 C29 H29 119.4 . . ?
C30 C29 H29 119.4 . . ?
C25 C30 C29 119.5(6) . . ?
C25 C30 H30 120.3 . . ?
C29 C30 H30 120.3 . . ?
C32 C31 C36 118.8(5) . . ?
C32 C31 C18 120.1(4) . . ?
C36 C31 C18 121.0(4) . . ?
C31 C32 C33 121.6(6) . . ?
C31 C32 H32 119.2 . . ?
C33 C32 H32 119.2 . . ?
C34 C33 C32 118.4(7) . . ?
C34 C33 H33 120.8 . . ?
C32 C33 H33 120.8 . . ?
C33 C34 C35 121.9(6) . . ?
C33 C34 H34 119.0 . . ?
C35 C34 H34 119.0 . . ?
C34 C35 C36 119.7(7) . . ?
C34 C35 H35 120.1 . . ?
C36 C35 H35 120.1 . . ?
C31 C36 C35 119.5(6) . . ?
C31 C36 H36 120.2 . . ?
C35 C36 H36 120.2 . . ?
C42 C37 C38 115.8(4) . . ?
C42 C37 B2 121.2(4) . . ?
C38 C37 B2 123.0(4) . . ?
C39 C38 C37 122.1(5) . . ?
C39 C38 H38 119.0 . . ?
C37 C38 H38 119.0 . . ?
C38 C39 C40 120.1(5) . . ?
C38 C39 H39 119.9 . . ?
C40 C39 H39 119.9 . . ?
C41 C40 C39 119.9(5) . . ?
C41 C40 H40 120.1 . . ?
C39 C40 H40 120.1 . . ?
C40 C41 C42 120.3(6) . . ?
C40 C41 H41 119.9 . . ?
C42 C41 H41 119.9 . . ?
C41 C42 C37 121.8(6) . . ?
C41 C42 H42 119.1 . . ?
C37 C42 H42 119.1 . . ?
C48 C43 C44 116.3(4) . . ?
C48 C43 B2 123.7(4) . . ?
C44 C43 B2 119.9(4) . . ?
C45 C44 C43 121.8(4) . . ?
C45 C44 H44 119.1 . . ?
C43 C44 H44 119.1 . . ?
C46 C45 C44 121.3(5) . . ?
C46 C45 H45 119.3 . . ?
C44 C45 H45 119.3 . . ?
C45 C46 C47 118.5(5) . . ?
C45 C46 H46 120.7 . . ?
C47 C46 H46 120.7 . . ?
C46 C47 C48 120.5(5) . . ?
C46 C47 H47 119.7 . . ?
C48 C47 H47 119.7 . . ?
C43 C48 C47 121.5(4) . . ?
C43 C48 H48 119.3 . . ?
C47 C48 H48 119.3 . . ?

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
C9 O1 B2 C37 -93.8(4) . . . . ?
C9 O1 B2 C43 137.2(4) . . . . ?
C9 O1 B2 N3 21.8(5) . . . . ?
O1 B2 N3 C4 -13.7(5) . . . . ?
C37 B2 N3 C4 103.8(4) . . . . ?
C43 B2 N3 C4 -128.4(4) . . . . ?
O1 B2 N3 C11 173.4(3) . . . . ?
C37 B2 N3 C11 -69.1(4) . . . . ?
C43 B2 N3 C11 58.7(4) . . . . ?
C11 N3 C4 C10 176.3(3) . . . . ?
B2 N3 C4 C10 3.0(6) . . . . ?
C10 C5 C6 C7 1.2(6) . . . . ?
C10 C5 C6 I2 -177.3(3) . . . . ?
C5 C6 C7 C8 0.3(7) . . . . ?
I2 C6 C7 C8 178.7(3) . . . . ?
C6 C7 C8 C9 -1.1(6) . . . . ?
C6 C7 C8 I1 179.6(3) . . . . ?
B2 O1 C9 C10 -18.6(6) . . . . ?
B2 O1 C9 C8 163.7(4) . . . . ?
C7 C8 C9 O1 178.1(4) . . . . ?
I1 C8 C9 O1 -2.6(5) . . . . ?
C7 C8 C9 C10 0.3(6) . . . . ?
I1 C8 C9 C10 179.7(3) . . . . ?
O1 C9 C10 C5 -176.6(4) . . . . ?
C8 C9 C10 C5 1.2(6) . . . . ?
O1 C9 C10 C4 3.7(6) . . . . ?
C8 C9 C10 C4 -178.6(4) . . . . ?
C6 C5 C10 C9 -1.9(6) . . . . ?
C6 C5 C10 C4 177.8(4) . . . . ?
N3 C4 C10 C9 3.4(6) . . . . ?
N3 C4 C10 C5 -176.3(4) . . . . ?
C4 N3 C11 C12 -55.4(5) . . . . ?
B2 N3 C11 C12 117.9(4) . . . . ?
C4 N3 C11 C16 124.1(4) . . . . ?
B2 N3 C11 C16 -62.6(5) . . . . ?
C16 C11 C12 C13 0.1(6) . . . . ?
N3 C11 C12 C13 179.6(3) . . . . ?
C11 C12 C13 C14 0.9(6) . . . . ?
C12 C13 C14 C15 -1.3(6) . . . . ?
C12 C13 C14 C17 -178.2(4) . . . . ?
C13 C14 C15 C16 0.8(6) . . . . ?
C17 C14 C15 C16 177.8(4) . . . . ?
C12 C11 C16 C15 -0.6(6) . . . . ?
N3 C11 C16 C15 179.9(3) . . . . ?
C14 C15 C16 C11 0.1(6) . . . . ?
C13 C14 C17 C18 -128.5(4) . . . . ?
C15 C14 C17 C18 54.7(5) . . . . ?
C13 C14 C17 C19 55.2(5) . . . . ?
C15 C14 C17 C19 -121.6(4) . . . . ?
C19 C17 C18 C31 -172.2(4) . . . . ?
C14 C17 C18 C31 11.9(6) . . . . ?
C19 C17 C18 C25 11.4(6) . . . . ?
C14 C17 C18 C25 -164.5(4) . . . . ?
C18 C17 C19 C20 -140.2(4) . . . . ?
C14 C17 C19 C20 36.0(5) . . . . ?
C18 C17 C19 C24 39.6(6) . . . . ?
C14 C17 C19 C24 -144.3(4) . . . . ?
C24 C19 C20 C21 -1.0(7) . . . . ?
C17 C19 C20 C21 178.7(4) . . . . ?
C19 C20 C21 C22 -0.3(8) . . . . ?
C20 C21 C22 C23 0.7(8) . . . . ?
C21 C22 C23 C24 0.3(7) . . . . ?
C22 C23 C24 C19 -1.7(7) . . . . ?
C20 C19 C24 C23 2.0(6) . . . . ?
C17 C19 C24 C23 -177.8(4) . . . . ?
C17 C18 C25 C26 51.6(6) . . . . ?
C31 C18 C25 C26 -125.0(5) . . . . ?
C17 C18 C25 C30 -128.8(5) . . . . ?
C31 C18 C25 C30 54.5(6) . . . . ?
C30 C25 C26 C27 1.1(8) . . . . ?
C18 C25 C26 C27 -179.4(5) . . . . ?
C25 C26 C27 C28 -2.0(10) . . . . ?
C26 C27 C28 C29 2.7(10) . . . . ?
C27 C28 C29 C30 -2.6(10) . . . . ?
C26 C25 C30 C29 -1.0(8) . . . . ?
C18 C25 C30 C29 179.5(5) . . . . ?
C28 C29 C30 C25 1.8(9) . . . . ?
C17 C18 C31 C32 -125.7(5) . . . . ?
C25 C18 C31 C32 50.9(5) . . . . ?
C17 C18 C31 C36 53.7(6) . . . . ?
C25 C18 C31 C36 -129.6(4) . . . . ?
C36 C31 C32 C33 -1.0(7) . . . . ?
C18 C31 C32 C33 178.4(5) . . . . ?
C31 C32 C33 C34 1.3(9) . . . . ?
C32 C33 C34 C35 -1.3(11) . . . . ?
C33 C34 C35 C36 1.1(11) . . . . ?
C32 C31 C36 C35 0.7(7) . . . . ?
C18 C31 C36 C35 -178.7(5) . . . . ?
C34 C35 C36 C31 -0.8(9) . . . . ?
O1 B2 C37 C42 -12.0(6) . . . . ?
C43 B2 C37 C42 111.6(5) . . . . ?
N3 B2 C37 C42 -125.8(4) . . . . ?
O1 B2 C37 C38 168.9(4) . . . . ?
C43 B2 C37 C38 -67.6(5) . . . . ?
N3 B2 C37 C38 55.0(5) . . . . ?
C42 C37 C38 C39 2.1(6) . . . . ?
B2 C37 C38 C39 -178.7(4) . . . . ?
C37 C38 C39 C40 -1.8(8) . . . . ?
C38 C39 C40 C41 0.5(9) . . . . ?
C39 C40 C41 C42 0.5(10) . . . . ?
C40 C41 C42 C37 -0.2(9) . . . . ?
C38 C37 C42 C41 -1.1(7) . . . . ?
B2 C37 C42 C41 179.7(5) . . . . ?
O1 B2 C43 C48 145.1(4) . . . . ?
C37 B2 C43 C48 20.1(6) . . . . ?
N3 B2 C43 C48 -101.9(5) . . . . ?
O1 B2 C43 C44 -37.5(5) . . . . ?
C37 B2 C43 C44 -162.5(4) . . . . ?
N3 B2 C43 C44 75.5(4) . . . . ?
C48 C43 C44 C45 0.3(7) . . . . ?
B2 C43 C44 C45 -177.2(5) . . . . ?
C43 C44 C45 C46 1.0(9) . . . . ?
C44 C45 C46 C47 -1.0(9) . . . . ?
C45 C46 C47 C48 -0.2(9) . . . . ?
C44 C43 C48 C47 -1.5(7) . . . . ?
B2 C43 C48 C47 175.9(5) . . . . ?
C46 C47 C48 C43 1.5(8) . . . . ?

_refine_diff_density_max         1.625
_refine_diff_density_min         -0.770
_refine_diff_density_rms         0.101

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_3a-MCGG-BRM
_database_code_depnum_ccdc_archive 'CCDC 2075071'
loop_
_audit_author_name
_audit_author_address
'Ruben A. Toscano'
;Institute of Chemistry, UNAM
Mexico
;
_audit_update_record             
;
2021-04-02 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;
_audit_creation_date             2020-07-21
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          493-494
_chemical_formula_moiety         'C33 H22 B Cl2 F2 N O'
_chemical_formula_sum            'C33 H22 B Cl2 F2 N O'
_chemical_formula_weight         568.22

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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.0896(4)
_cell_length_b                   9.3799(6)
_cell_length_c                   24.4891(15)
_cell_angle_alpha                84.352(2)
_cell_angle_beta                 86.909(2)
_cell_angle_gamma                87.232(2)
_cell_volume                     1388.70(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9933
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      30.07

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.069
_exptl_absorpt_coefficient_mu    0.275
_shelx_estimated_absorpt_T_min   0.910
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5182
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus X-ray source'
_diffrn_radiation_monochromator  'Helios multilayer mirror'
_diffrn_measurement_device_type  
'Bruker D8 Venture κ geometry diffractometer 208039-1'
_diffrn_measurement_method       'φ and ω-scans'
_diffrn_detector_area_resol_mean 52.0833
_diffrn_reflns_number            37443
_diffrn_reflns_av_unetI/netI     0.0969
_diffrn_reflns_av_R_equivalents  0.1040
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.184
_diffrn_reflns_theta_max         29.573
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7777
_reflns_number_gt                4492
_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 v2018.1-0(Bruker, 2018)'
_computing_cell_refinement       'APEX3 v2018.1-0(Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2014)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXLe (HÃ1/4bschle et al, 2011)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_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)+(0.0296P)²+0.6121P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7777
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1301
_refine_ls_R_factor_gt           0.0613
_refine_ls_wR_factor_ref         0.1212
_refine_ls_wR_factor_gt          0.1016
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.00546(10) 0.26956(7) 0.64028(3) 0.04434(18) Uani 1 1 d . . . . .
Cl2 Cl 0.76473(10) 0.00063(6) 0.57574(2) 0.03760(16) Uani 1 1 d . . . . .
F1 F 0.8077(2) 0.19126(14) 0.37903(5) 0.0376(3) Uani 1 1 d . . . . .
F2 F 0.85664(19) 0.37454(14) 0.43078(6) 0.0381(3) Uani 1 1 d . . . . .
O1 O 0.6930(2) 0.16780(16) 0.47049(6) 0.0285(4) Uani 1 1 d . . . . .
B2 B 0.7224(4) 0.2647(3) 0.42162(11) 0.0263(6) Uani 1 1 d . . . . .
N3 N 0.4930(3) 0.34069(18) 0.40546(7) 0.0231(4) Uani 1 1 d . . . . .
C4 C 0.3400(3) 0.3541(2) 0.44333(9) 0.0247(5) Uani 1 1 d . . . . .
H4 H 0.209966 0.409706 0.434435 0.030 Uiso 1 1 calc R U . . .
C5 C 0.1924(3) 0.3106(2) 0.53838(9) 0.0289(5) Uani 1 1 d . . . . .
H5 H 0.069189 0.373704 0.530240 0.035 Uiso 1 1 calc R U . . .
C6 C 0.2088(4) 0.2408(2) 0.58945(9) 0.0309(5) Uani 1 1 d . . . . .
C7 C 0.3858(4) 0.1453(2) 0.60164(9) 0.0339(5) Uani 1 1 d . . . . .
H7 H 0.394882 0.096720 0.637418 0.041 Uiso 1 1 calc R U . . .
C8 C 0.5474(4) 0.1216(2) 0.56159(9) 0.0292(5) Uani 1 1 d . . . . .
C9 C 0.5389(3) 0.1938(2) 0.50931(9) 0.0247(5) Uani 1 1 d . . . . .
C10 C 0.3584(3) 0.2888(2) 0.49793(9) 0.0259(5) Uani 1 1 d . . . . .
C11 C 0.3420(3) 0.5621(2) 0.18427(9) 0.0289(5) Uani 1 1 d . . . . .
C12 C 0.3881(3) 0.6936(2) 0.16096(9) 0.0298(5) Uani 1 1 d . . . . .
C13 C 0.4553(3) 0.3990(2) 0.35012(9) 0.0243(5) Uani 1 1 d . . . . .
C14 C 0.6160(3) 0.4761(2) 0.31987(9) 0.0286(5) Uani 1 1 d . . . . .
H14 H 0.752164 0.489664 0.335400 0.034 Uiso 1 1 calc R U . . .
C15 C 0.5770(4) 0.5330(2) 0.26701(9) 0.0317(5) Uani 1 1 d . . . . .
H15 H 0.686481 0.587360 0.246523 0.038 Uiso 1 1 calc R U . . .
C16 C 0.3795(3) 0.5122(2) 0.24308(9) 0.0271(5) Uani 1 1 d . . . . .
C17 C 0.2235(3) 0.4318(2) 0.27409(9) 0.0292(5) Uani 1 1 d . . . . .
H17 H 0.088899 0.415262 0.258365 0.035 Uiso 1 1 calc R U . . .
C18 C 0.2591(3) 0.3756(2) 0.32699(9) 0.0279(5) Uani 1 1 d . . . . .
H18 H 0.149910 0.321141 0.347552 0.033 Uiso 1 1 calc R U . . .
C19 C 0.2508(3) 0.4515(2) 0.15322(9) 0.0277(5) Uani 1 1 d . . . . .
C20 C 0.0668(4) 0.4782(3) 0.12199(10) 0.0386(6) Uani 1 1 d . . . . .
H20 H -0.000512 0.571925 0.118170 0.046 Uiso 1 1 calc R U . . .
C21 C -0.0194(4) 0.3702(3) 0.09644(12) 0.0476(7) Uani 1 1 d . . . . .
H21 H -0.144560 0.390238 0.074964 0.057 Uiso 1 1 calc R U . . .
C22 C 0.0751(4) 0.2331(3) 0.10192(11) 0.0427(6) Uani 1 1 d . . . . .
H22 H 0.015058 0.158799 0.084474 0.051 Uiso 1 1 calc R U . . .
C23 C 0.2569(4) 0.2050(3) 0.13280(10) 0.0370(6) Uani 1 1 d . . . . .
H23 H 0.322589 0.110871 0.136810 0.044 Uiso 1 1 calc R U . . .
C24 C 0.3438(4) 0.3129(2) 0.15791(9) 0.0320(5) Uani 1 1 d . . . . .
H24 H 0.470137 0.292193 0.178906 0.038 Uiso 1 1 calc R U . . .
C25 C 0.4476(4) 0.8112(2) 0.19377(9) 0.0285(5) Uani 1 1 d . . . . .
C26 C 0.3073(4) 0.8565(2) 0.23579(9) 0.0354(6) Uani 1 1 d . . . . .
H26 H 0.172459 0.810735 0.244585 0.042 Uiso 1 1 calc R U . . .
C27 C 0.3613(5) 0.9672(3) 0.26490(10) 0.0421(6) Uani 1 1 d . . . . .
H27 H 0.262791 0.997789 0.293266 0.051 Uiso 1 1 calc R U . . .
C28 C 0.5563(5) 1.0334(3) 0.25315(11) 0.0444(7) Uani 1 1 d . . . . .
H28 H 0.593577 1.108372 0.273889 0.053 Uiso 1 1 calc R U . . .
C29 C 0.6983(4) 0.9918(3) 0.21149(11) 0.0445(7) Uani 1 1 d . . . . .
H29 H 0.833368 1.037863 0.203361 0.053 Uiso 1 1 calc R U . . .
C30 C 0.6428(4) 0.8816(3) 0.18131(10) 0.0381(6) Uani 1 1 d . . . . .
H30 H 0.739017 0.854152 0.151954 0.046 Uiso 1 1 calc R U . . .
C31 C 0.3835(4) 0.7334(2) 0.10063(9) 0.0287(5) Uani 1 1 d . . . . .
C32 C 0.2636(4) 0.8540(2) 0.07991(10) 0.0314(5) Uani 1 1 d . . . . .
H32 H 0.178116 0.909618 0.104333 0.038 Uiso 1 1 calc R U . . .
C33 C 0.2672(4) 0.8943(3) 0.02405(10) 0.0387(6) Uani 1 1 d . . . . .
H33 H 0.184043 0.977223 0.010357 0.046 Uiso 1 1 calc R U . . .
C34 C 0.3904(4) 0.8150(3) -0.01183(10) 0.0425(6) Uani 1 1 d . . . . .
H34 H 0.392357 0.842887 -0.050211 0.051 Uiso 1 1 calc R U . . .
C35 C 0.5107(4) 0.6954(3) 0.00813(10) 0.0446(7) Uani 1 1 d . . . . .
H35 H 0.596771 0.640421 -0.016404 0.054 Uiso 1 1 calc R U . . .
C36 C 0.5062(4) 0.6553(3) 0.06373(10) 0.0397(6) Uani 1 1 d . . . . .
H36 H 0.589339 0.572099 0.077124 0.048 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
Cl1 C6 1.739(2) . ?
Cl2 C8 1.728(2) . ?
F1 B2 1.371(3) . ?
F2 B2 1.388(3) . ?
O1 C9 1.331(2) . ?
O1 B2 1.439(3) . ?
B2 N3 1.589(3) . ?
N3 C4 1.289(2) . ?
N3 C13 1.436(3) . ?
C4 C10 1.423(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.360(3) . ?
C5 C10 1.399(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.394(3) . ?
C7 C8 1.378(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.391(3) . ?
C9 C10 1.403(3) . ?
C11 C12 1.344(3) . ?
C11 C19 1.490(3) . ?
C11 C16 1.496(3) . ?
C12 C31 1.489(3) . ?
C12 C25 1.495(3) . ?
C13 C14 1.383(3) . ?
C13 C18 1.386(3) . ?
C14 C15 1.379(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.396(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.388(3) . ?
C17 C18 1.374(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C24 1.389(3) . ?
C19 C20 1.390(3) . ?
C20 C21 1.380(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.380(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.375(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.375(3) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C26 1.388(3) . ?
C25 C30 1.393(3) . ?
C26 C27 1.377(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.370(4) . ?
C27 H27 0.9500 . ?
C28 C29 1.376(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.393(3) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C36 1.384(3) . ?
C31 C32 1.385(3) . ?
C32 C33 1.382(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.375(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.373(4) . ?
C34 H34 0.9500 . ?
C35 C36 1.376(3) . ?
C35 H35 0.9500 . ?
C36 H36 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
C9 O1 B2 121.38(17) . . ?
F1 B2 F2 110.98(18) . . ?
F1 B2 O1 110.02(19) . . ?
F2 B2 O1 110.76(19) . . ?
F1 B2 N3 109.24(18) . . ?
F2 B2 N3 105.72(18) . . ?
O1 B2 N3 110.03(17) . . ?
C4 N3 C13 119.45(17) . . ?
C4 N3 B2 119.02(18) . . ?
C13 N3 B2 121.49(16) . . ?
N3 C4 C10 122.50(19) . . ?
N3 C4 H4 118.7 . . ?
C10 C4 H4 118.7 . . ?
C6 C5 C10 119.4(2) . . ?
C6 C5 H5 120.3 . . ?
C10 C5 H5 120.3 . . ?
C5 C6 C7 120.9(2) . . ?
C5 C6 Cl1 119.74(18) . . ?
C7 C6 Cl1 119.31(18) . . ?
C8 C7 C6 119.7(2) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C9 120.9(2) . . ?
C7 C8 Cl2 120.19(18) . . ?
C9 C8 Cl2 118.91(17) . . ?
O1 C9 C8 120.50(19) . . ?
O1 C9 C10 121.11(19) . . ?
C8 C9 C10 118.3(2) . . ?
C5 C10 C9 120.6(2) . . ?
C5 C10 C4 120.72(19) . . ?
C9 C10 C4 118.46(19) . . ?
C12 C11 C19 122.6(2) . . ?
C12 C11 C16 123.6(2) . . ?
C19 C11 C16 113.82(19) . . ?
C11 C12 C31 122.6(2) . . ?
C11 C12 C25 122.4(2) . . ?
C31 C12 C25 115.03(19) . . ?
C14 C13 C18 120.3(2) . . ?
C14 C13 N3 120.01(18) . . ?
C18 C13 N3 119.70(19) . . ?
C15 C14 C13 119.5(2) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 121.2(2) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C17 C16 C15 117.9(2) . . ?
C17 C16 C11 119.94(19) . . ?
C15 C16 C11 121.9(2) . . ?
C18 C17 C16 121.6(2) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C18 C13 119.5(2) . . ?
C17 C18 H18 120.2 . . ?
C13 C18 H18 120.2 . . ?
C24 C19 C20 117.8(2) . . ?
C24 C19 C11 119.27(19) . . ?
C20 C19 C11 122.8(2) . . ?
C21 C20 C19 120.8(2) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C22 C21 C20 120.4(2) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C23 C22 C21 119.5(2) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C22 C23 C24 120.1(2) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C23 C24 C19 121.4(2) . . ?
C23 C24 H24 119.3 . . ?
C19 C24 H24 119.3 . . ?
C26 C25 C30 118.3(2) . . ?
C26 C25 C12 121.3(2) . . ?
C30 C25 C12 120.4(2) . . ?
C27 C26 C25 120.8(2) . . ?
C27 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C28 C27 C26 120.3(3) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C27 C28 C29 120.3(2) . . ?
C27 C28 H28 119.8 . . ?
C29 C28 H28 119.8 . . ?
C28 C29 C30 119.5(2) . . ?
C28 C29 H29 120.2 . . ?
C30 C29 H29 120.2 . . ?
C25 C30 C29 120.6(2) . . ?
C25 C30 H30 119.7 . . ?
C29 C30 H30 119.7 . . ?
C36 C31 C32 117.9(2) . . ?
C36 C31 C12 121.31(19) . . ?
C32 C31 C12 120.7(2) . . ?
C33 C32 C31 120.6(2) . . ?
C33 C32 H32 119.7 . . ?
C31 C32 H32 119.7 . . ?
C34 C33 C32 120.4(2) . . ?
C34 C33 H33 119.8 . . ?
C32 C33 H33 119.8 . . ?
C35 C34 C33 119.6(2) . . ?
C35 C34 H34 120.2 . . ?
C33 C34 H34 120.2 . . ?
C34 C35 C36 119.8(2) . . ?
C34 C35 H35 120.1 . . ?
C36 C35 H35 120.1 . . ?
C35 C36 C31 121.6(2) . . ?
C35 C36 H36 119.2 . . ?
C31 C36 H36 119.2 . . ?

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
C9 O1 B2 F1 -152.11(17) . . . . ?
C9 O1 B2 F2 84.8(2) . . . . ?
C9 O1 B2 N3 -31.7(3) . . . . ?
F1 B2 N3 C4 146.56(19) . . . . ?
F2 B2 N3 C4 -93.9(2) . . . . ?
O1 B2 N3 C4 25.7(3) . . . . ?
F1 B2 N3 C13 -35.7(3) . . . . ?
F2 B2 N3 C13 83.8(2) . . . . ?
O1 B2 N3 C13 -156.54(18) . . . . ?
C13 N3 C4 C10 174.56(19) . . . . ?
B2 N3 C4 C10 -7.6(3) . . . . ?
C10 C5 C6 C7 -1.6(3) . . . . ?
C10 C5 C6 Cl1 178.93(16) . . . . ?
C5 C6 C7 C8 0.4(3) . . . . ?
Cl1 C6 C7 C8 179.86(17) . . . . ?
C6 C7 C8 C9 1.2(3) . . . . ?
C6 C7 C8 Cl2 -178.65(17) . . . . ?
B2 O1 C9 C8 -163.40(19) . . . . ?
B2 O1 C9 C10 19.8(3) . . . . ?
C7 C8 C9 O1 -178.43(19) . . . . ?
Cl2 C8 C9 O1 1.5(3) . . . . ?
C7 C8 C9 C10 -1.6(3) . . . . ?
Cl2 C8 C9 C10 178.32(16) . . . . ?
C6 C5 C10 C9 1.2(3) . . . . ?
C6 C5 C10 C4 176.5(2) . . . . ?
O1 C9 C10 C5 177.19(19) . . . . ?
C8 C9 C10 C5 0.3(3) . . . . ?
O1 C9 C10 C4 1.8(3) . . . . ?
C8 C9 C10 C4 -175.02(19) . . . . ?
N3 C4 C10 C5 177.5(2) . . . . ?
N3 C4 C10 C9 -7.2(3) . . . . ?
C19 C11 C12 C31 -9.2(3) . . . . ?
C16 C11 C12 C31 169.93(19) . . . . ?
C19 C11 C12 C25 170.70(19) . . . . ?
C16 C11 C12 C25 -10.2(3) . . . . ?
C4 N3 C13 C14 135.1(2) . . . . ?
B2 N3 C13 C14 -42.7(3) . . . . ?
C4 N3 C13 C18 -45.9(3) . . . . ?
B2 N3 C13 C18 136.3(2) . . . . ?
C18 C13 C14 C15 1.8(3) . . . . ?
N3 C13 C14 C15 -179.21(19) . . . . ?
C13 C14 C15 C16 -1.1(3) . . . . ?
C14 C15 C16 C17 -0.2(3) . . . . ?
C14 C15 C16 C11 -174.6(2) . . . . ?
C12 C11 C16 C17 138.4(2) . . . . ?
C19 C11 C16 C17 -42.3(3) . . . . ?
C12 C11 C16 C15 -47.3(3) . . . . ?
C19 C11 C16 C15 131.9(2) . . . . ?
C15 C16 C17 C18 0.9(3) . . . . ?
C11 C16 C17 C18 175.4(2) . . . . ?
C16 C17 C18 C13 -0.2(3) . . . . ?
C14 C13 C18 C17 -1.2(3) . . . . ?
N3 C13 C18 C17 179.85(19) . . . . ?
C12 C11 C19 C24 132.8(2) . . . . ?
C16 C11 C19 C24 -46.5(3) . . . . ?
C12 C11 C19 C20 -51.2(3) . . . . ?
C16 C11 C19 C20 129.6(2) . . . . ?
C24 C19 C20 C21 -0.2(4) . . . . ?
C11 C19 C20 C21 -176.3(2) . . . . ?
C19 C20 C21 C22 0.5(4) . . . . ?
C20 C21 C22 C23 -0.4(4) . . . . ?
C21 C22 C23 C24 -0.1(4) . . . . ?
C22 C23 C24 C19 0.5(4) . . . . ?
C20 C19 C24 C23 -0.3(3) . . . . ?
C11 C19 C24 C23 175.9(2) . . . . ?
C11 C12 C25 C26 -57.5(3) . . . . ?
C31 C12 C25 C26 122.4(2) . . . . ?
C11 C12 C25 C30 124.9(2) . . . . ?
C31 C12 C25 C30 -55.1(3) . . . . ?
C30 C25 C26 C27 -0.8(3) . . . . ?
C12 C25 C26 C27 -178.4(2) . . . . ?
C25 C26 C27 C28 -0.7(4) . . . . ?
C26 C27 C28 C29 1.2(4) . . . . ?
C27 C28 C29 C30 -0.1(4) . . . . ?
C26 C25 C30 C29 1.9(3) . . . . ?
C12 C25 C30 C29 179.6(2) . . . . ?
C28 C29 C30 C25 -1.5(4) . . . . ?
C11 C12 C31 C36 -55.0(3) . . . . ?
C25 C12 C31 C36 125.1(2) . . . . ?
C11 C12 C31 C32 128.0(2) . . . . ?
C25 C12 C31 C32 -51.9(3) . . . . ?
C36 C31 C32 C33 0.1(3) . . . . ?
C12 C31 C32 C33 177.2(2) . . . . ?
C31 C32 C33 C34 -0.1(4) . . . . ?
C32 C33 C34 C35 -0.1(4) . . . . ?
C33 C34 C35 C36 0.3(4) . . . . ?
C34 C35 C36 C31 -0.3(4) . . . . ?
C32 C31 C36 C35 0.1(4) . . . . ?
C12 C31 C36 C35 -176.9(2) . . . . ?

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
C4 H4 F2 0.95 2.20 2.971(2) 137.5 1_455 yes
C14 H14 Cl1 0.95 2.88 3.632(2) 136.5 2_666 yes
C14 H14 F2 0.95 2.57 3.196(3) 123.4 . yes
C18 H18 F1 0.95 2.51 3.438(2) 164.8 1_455 yes

_refine_diff_density_max         0.329
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.062

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_3c-MCGG-BRM
_database_code_depnum_ccdc_archive 'CCDC 2075070'
loop_
_audit_author_name
_audit_author_address
'Ruben A. Toscano'
;Institute of Chemistry, UNAM
Mexico
;
_audit_update_record             
;
2021-04-02 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;
_audit_creation_date             2020-07-21
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          458-459
_chemical_formula_moiety         'C33 H22 B F2 I2 N O'
_chemical_formula_sum            'C33 H22 B F2 I2 N O'
_chemical_formula_weight         751.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0017 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0065 0.0035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0115 0.0064 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0185 0.0109 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3993 1.9038 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.2357(3)
_cell_length_b                   9.7731(4)
_cell_length_c                   24.6541(10)
_cell_angle_alpha                79.7070(10)
_cell_angle_beta                 88.857(2)
_cell_angle_gamma                85.753(2)
_cell_volume                     1474.20(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9498
_cell_measurement_theta_min      2.5247
_cell_measurement_theta_max      34.1555

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.692
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   0.6873
_exptl_transmission_factor_max   0.7467
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.015
_exptl_absorpt_coefficient_mu    2.294
_shelx_estimated_absorpt_T_min   0.739
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.889
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_process_details   'SADABS 2016/2 Bruker AXS Madison WI USA'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.7288
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source beamline 12.2.1'
_diffrn_measurement_device_type  'Bruker D8 with PHOTONII detector'
_diffrn_measurement_method       'ω/θ shutterless scans'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            44417
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         1.722
_diffrn_reflns_theta_max         34.190
_diffrn_reflns_theta_full        25.930
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             11143
_reflns_number_gt                10241
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX 3'
_computing_cell_refinement       'Bruker SAINT v8.38a'
_computing_data_reduction        'Bruker SAINT v8.38a'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL & local programs'
_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)+(0.0095P)²+1.7209P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'Dual space'
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         11143
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_ref         0.0634
_refine_ls_wR_factor_gt          0.0604
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_restrained_S_all      1.151
_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
I1 I 0.18708(2) 1.02014(2) 0.41983(2) 0.01500(3) Uani 1 1 d . . . . .
I2 I 1.00158(2) 0.71857(2) 0.35238(2) 0.01754(3) Uani 1 1 d . . . . .
F1 F 0.20853(19) 0.78512(13) 0.62158(5) 0.0216(3) Uani 1 1 d . . . . .
F2 F 0.16818(19) 0.61547(13) 0.57101(5) 0.0221(3) Uani 1 1 d . . . . .
O1 O 0.3202(2) 0.82164(14) 0.53077(5) 0.0146(3) Uani 1 1 d . . . . .
N1 N 0.5245(2) 0.64592(16) 0.59931(6) 0.0120(3) Uani 1 1 d . . . . .
C1 C 0.6831(3) 0.4254(2) 0.82691(8) 0.0156(3) Uani 1 1 d . . . . .
C2 C 0.6325(3) 0.2966(2) 0.85222(8) 0.0157(3) Uani 1 1 d . . . . .
C3 C 0.6455(3) 0.4773(2) 0.76678(8) 0.0144(3) Uani 1 1 d . . . . .
C4 C 0.4481(3) 0.4643(2) 0.74276(8) 0.0168(4) Uani 1 1 d . . . . .
H4 H 0.339949 0.416122 0.764333 0.020 Uiso 1 1 calc R U . . .
C5 C 0.4084(3) 0.5210(2) 0.68785(8) 0.0161(3) Uani 1 1 d . . . . .
H5 H 0.273344 0.512594 0.672063 0.019 Uiso 1 1 calc R U . . .
C6 C 0.5675(3) 0.58999(19) 0.65607(7) 0.0127(3) Uani 1 1 d . . . . .
C7 C 0.7630(3) 0.6063(2) 0.67926(8) 0.0140(3) Uani 1 1 d . . . . .
H7 H 0.870248 0.655348 0.657648 0.017 Uiso 1 1 calc R U . . .
C8 C 0.8000(3) 0.5503(2) 0.73430(8) 0.0144(3) Uani 1 1 d . . . . .
H8 H 0.933381 0.561981 0.750229 0.017 Uiso 1 1 calc R U . . .
C9 C 0.7717(3) 0.5295(2) 0.85622(8) 0.0157(3) Uani 1 1 d . . . . .
C10 C 0.6919(3) 0.6689(2) 0.84416(8) 0.0179(4) Uani 1 1 d . . . . .
H10 H 0.578410 0.695094 0.818420 0.022 Uiso 1 1 calc R U . . .
C11 C 0.7752(4) 0.7696(2) 0.86904(9) 0.0210(4) Uani 1 1 d . . . . .
H11 H 0.719618 0.863961 0.860117 0.025 Uiso 1 1 calc R U . . .
C12 C 0.9405(4) 0.7324(2) 0.90710(10) 0.0247(4) Uani 1 1 d . . . . .
H12 H 0.997471 0.800923 0.924474 0.030 Uiso 1 1 calc R U . . .
C13 C 1.0214(4) 0.5944(2) 0.91949(10) 0.0251(4) Uani 1 1 d . . . . .
H13 H 1.133656 0.568441 0.945617 0.030 Uiso 1 1 calc R U . . .
C14 C 0.9395(3) 0.4939(2) 0.89396(9) 0.0202(4) Uani 1 1 d . . . . .
H14 H 0.998219 0.400132 0.902242 0.024 Uiso 1 1 calc R U . . .
C15 C 0.6310(3) 0.2540(2) 0.91320(8) 0.0159(3) Uani 1 1 d . . . . .
C16 C 0.5178(3) 0.3377(2) 0.94624(9) 0.0208(4) Uani 1 1 d . . . . .
H16 H 0.446957 0.423927 0.929615 0.025 Uiso 1 1 calc R U . . .
C17 C 0.5079(4) 0.2959(2) 1.00293(9) 0.0239(4) Uani 1 1 d . . . . .
H17 H 0.430519 0.353632 1.024905 0.029 Uiso 1 1 calc R U . . .
C18 C 0.6104(4) 0.1704(2) 1.02765(8) 0.0241(4) Uani 1 1 d . . . . .
H18 H 0.603969 0.142188 1.066539 0.029 Uiso 1 1 calc R U . . .
C19 C 0.7225(3) 0.0859(2) 0.99556(9) 0.0215(4) Uani 1 1 d . . . . .
H19 H 0.793398 -0.000075 1.012435 0.026 Uiso 1 1 calc R U . . .
C20 C 0.7311(3) 0.1273(2) 0.93859(8) 0.0192(4) Uani 1 1 d . . . . .
H20 H 0.806128 0.068332 0.916737 0.023 Uiso 1 1 calc R U . . .
C21 C 0.5680(3) 0.1885(2) 0.82120(8) 0.0163(3) Uani 1 1 d . . . . .
C22 C 0.6972(4) 0.1484(2) 0.77902(8) 0.0201(4) Uani 1 1 d . . . . .
H22 H 0.829793 0.189442 0.770148 0.024 Uiso 1 1 calc R U . . .
C23 C 0.6340(4) 0.0490(2) 0.74988(9) 0.0257(5) Uani 1 1 d . . . . .
H23 H 0.723943 0.021984 0.721511 0.031 Uiso 1 1 calc R U . . .
C24 C 0.4407(4) -0.0105(2) 0.76204(10) 0.0285(5) Uani 1 1 d . . . . .
H24 H 0.395863 -0.076475 0.741386 0.034 Uiso 1 1 calc R U . . .
C25 C 0.3122(4) 0.0262(2) 0.80454(10) 0.0280(5) Uani 1 1 d . . . . .
H25 H 0.180276 -0.015663 0.813348 0.034 Uiso 1 1 calc R U . . .
C26 C 0.3763(3) 0.1243(2) 0.83421(9) 0.0216(4) Uani 1 1 d . . . . .
H26 H 0.288789 0.147857 0.863637 0.026 Uiso 1 1 calc R U . . .
C27 C 0.6734(3) 0.63586(19) 0.56210(8) 0.0133(3) Uani 1 1 d . . . . .
H27 H 0.804721 0.582940 0.572545 0.016 Uiso 1 1 calc R U . . .
C28 C 0.6441(3) 0.70243(19) 0.50596(7) 0.0126(3) Uani 1 1 d . . . . .
C29 C 0.4656(3) 0.79804(19) 0.49261(7) 0.0123(3) Uani 1 1 d . . . . .
C30 C 0.4480(3) 0.87447(19) 0.43892(8) 0.0132(3) Uani 1 1 d . . . . .
C31 C 0.6000(3) 0.8513(2) 0.39931(8) 0.0152(3) Uani 1 1 d . . . . .
H31 H 0.585703 0.901913 0.362750 0.018 Uiso 1 1 calc R U . . .
C32 C 0.7745(3) 0.7535(2) 0.41292(8) 0.0145(3) Uani 1 1 d . . . . .
C33 C 0.7994(3) 0.6811(2) 0.46580(8) 0.0145(3) Uani 1 1 d . . . . .
H33 H 0.920829 0.617120 0.475096 0.017 Uiso 1 1 calc R U . . .
B1 B 0.2957(3) 0.7201(2) 0.58054(9) 0.0151(4) 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
I1 C30 2.0844(18) . ?
I2 C32 2.0916(19) . ?
F1 B1 1.371(2) . ?
F2 B1 1.395(3) . ?
O1 C29 1.331(2) . ?
O1 B1 1.447(3) . ?
N1 C27 1.303(2) . ?
N1 C6 1.431(2) . ?
N1 B1 1.590(3) . ?
C1 C2 1.358(3) . ?
C1 C9 1.492(3) . ?
C1 C3 1.496(3) . ?
C2 C15 1.487(3) . ?
C2 C21 1.492(3) . ?
C3 C8 1.395(3) . ?
C3 C4 1.400(3) . ?
C4 C5 1.388(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.388(2) . ?
C7 C8 1.386(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.397(3) . ?
C9 C14 1.397(3) . ?
C10 C11 1.385(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.391(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.387(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C20 1.393(3) . ?
C15 C16 1.400(3) . ?
C16 C17 1.386(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.385(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.386(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.391(3) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C26 1.396(3) . ?
C21 C22 1.397(3) . ?
C22 C23 1.390(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.381(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.388(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.390(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.429(3) . ?
C27 H27 0.9500 . ?
C28 C33 1.403(3) . ?
C28 C29 1.404(2) . ?
C29 C30 1.401(3) . ?
C30 C31 1.383(3) . ?
C31 C32 1.399(3) . ?
C31 H31 0.9500 . ?
C32 C33 1.373(3) . ?
C33 H33 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
C29 O1 B1 120.79(15) . . ?
C27 N1 C6 120.08(15) . . ?
C27 N1 B1 118.99(15) . . ?
C6 N1 B1 120.93(15) . . ?
C2 C1 C9 123.80(17) . . ?
C2 C1 C3 122.21(18) . . ?
C9 C1 C3 113.95(16) . . ?
C1 C2 C15 122.36(18) . . ?
C1 C2 C21 122.74(17) . . ?
C15 C2 C21 114.88(17) . . ?
C8 C3 C4 118.27(17) . . ?
C8 C3 C1 120.55(17) . . ?
C4 C3 C1 120.96(17) . . ?
C5 C4 C3 120.83(18) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 119.63(17) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C7 C6 C5 120.54(17) . . ?
C7 C6 N1 120.69(16) . . ?
C5 C6 N1 118.77(16) . . ?
C8 C7 C6 119.26(17) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C3 121.44(17) . . ?
C7 C8 H8 119.3 . . ?
C3 C8 H8 119.3 . . ?
C10 C9 C14 118.23(19) . . ?
C10 C9 C1 119.50(17) . . ?
C14 C9 C1 122.21(18) . . ?
C11 C10 C9 121.24(19) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 119.9(2) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 119.5(2) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C14 120.5(2) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C9 120.6(2) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?
C20 C15 C16 118.43(18) . . ?
C20 C15 C2 121.16(18) . . ?
C16 C15 C2 120.32(18) . . ?
C17 C16 C15 120.7(2) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C18 C17 C16 120.2(2) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 119.90(19) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C18 C19 C20 119.9(2) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C15 120.8(2) . . ?
C19 C20 H20 119.6 . . ?
C15 C20 H20 119.6 . . ?
C26 C21 C22 118.46(19) . . ?
C26 C21 C2 120.34(18) . . ?
C22 C21 C2 121.20(18) . . ?
C23 C22 C21 120.7(2) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C24 C23 C22 120.2(2) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C25 119.8(2) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C24 C25 C26 120.1(2) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C26 C21 120.7(2) . . ?
C25 C26 H26 119.7 . . ?
C21 C26 H26 119.7 . . ?
N1 C27 C28 121.65(16) . . ?
N1 C27 H27 119.2 . . ?
C28 C27 H27 119.2 . . ?
C33 C28 C29 120.52(17) . . ?
C33 C28 C27 120.60(16) . . ?
C29 C28 C27 118.69(16) . . ?
O1 C29 C30 120.00(16) . . ?
O1 C29 C28 120.97(16) . . ?
C30 C29 C28 118.94(16) . . ?
C31 C30 C29 120.19(17) . . ?
C31 C30 I1 120.98(14) . . ?
C29 C30 I1 118.82(13) . . ?
C30 C31 C32 120.20(17) . . ?
C30 C31 H31 119.9 . . ?
C32 C31 H31 119.9 . . ?
C33 C32 C31 120.62(17) . . ?
C33 C32 I2 119.66(14) . . ?
C31 C32 I2 119.72(14) . . ?
C32 C33 C28 119.46(17) . . ?
C32 C33 H33 120.3 . . ?
C28 C33 H33 120.3 . . ?
F1 B1 F2 110.70(16) . . ?
F1 B1 O1 109.72(16) . . ?
F2 B1 O1 110.79(17) . . ?
F1 B1 N1 109.47(16) . . ?
F2 B1 N1 106.67(15) . . ?
O1 B1 N1 109.43(15) . . ?

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
C9 C1 C2 C15 9.1(3) . . . . ?
C3 C1 C2 C15 -168.35(18) . . . . ?
C9 C1 C2 C21 -172.83(18) . . . . ?
C3 C1 C2 C21 9.8(3) . . . . ?
C2 C1 C3 C8 -137.6(2) . . . . ?
C9 C1 C3 C8 44.8(2) . . . . ?
C2 C1 C3 C4 47.9(3) . . . . ?
C9 C1 C3 C4 -129.76(19) . . . . ?
C8 C3 C4 C5 0.9(3) . . . . ?
C1 C3 C4 C5 175.57(18) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C4 C5 C6 C7 -2.0(3) . . . . ?
C4 C5 C6 N1 179.11(17) . . . . ?
C27 N1 C6 C7 41.5(3) . . . . ?
B1 N1 C6 C7 -138.89(18) . . . . ?
C27 N1 C6 C5 -139.58(19) . . . . ?
B1 N1 C6 C5 40.0(2) . . . . ?
C5 C6 C7 C8 1.4(3) . . . . ?
N1 C6 C7 C8 -179.70(17) . . . . ?
C6 C7 C8 C3 0.4(3) . . . . ?
C4 C3 C8 C7 -1.5(3) . . . . ?
C1 C3 C8 C7 -176.18(18) . . . . ?
C2 C1 C9 C10 -136.5(2) . . . . ?
C3 C1 C9 C10 41.1(2) . . . . ?
C2 C1 C9 C14 46.4(3) . . . . ?
C3 C1 C9 C14 -136.03(19) . . . . ?
C14 C9 C10 C11 -0.4(3) . . . . ?
C1 C9 C10 C11 -177.67(19) . . . . ?
C9 C10 C11 C12 -0.5(3) . . . . ?
C10 C11 C12 C13 0.5(3) . . . . ?
C11 C12 C13 C14 0.4(4) . . . . ?
C12 C13 C14 C9 -1.2(3) . . . . ?
C10 C9 C14 C13 1.2(3) . . . . ?
C1 C9 C14 C13 178.4(2) . . . . ?
C1 C2 C15 C20 -132.6(2) . . . . ?
C21 C2 C15 C20 49.2(3) . . . . ?
C1 C2 C15 C16 51.1(3) . . . . ?
C21 C2 C15 C16 -127.2(2) . . . . ?
C20 C15 C16 C17 0.8(3) . . . . ?
C2 C15 C16 C17 177.2(2) . . . . ?
C15 C16 C17 C18 0.0(3) . . . . ?
C16 C17 C18 C19 -0.3(3) . . . . ?
C17 C18 C19 C20 -0.2(3) . . . . ?
C18 C19 C20 C15 1.0(3) . . . . ?
C16 C15 C20 C19 -1.3(3) . . . . ?
C2 C15 C20 C19 -177.69(19) . . . . ?
C1 C2 C21 C26 -126.4(2) . . . . ?
C15 C2 C21 C26 51.8(2) . . . . ?
C1 C2 C21 C22 54.1(3) . . . . ?
C15 C2 C21 C22 -127.6(2) . . . . ?
C26 C21 C22 C23 1.4(3) . . . . ?
C2 C21 C22 C23 -179.10(19) . . . . ?
C21 C22 C23 C24 0.6(3) . . . . ?
C22 C23 C24 C25 -1.8(3) . . . . ?
C23 C24 C25 C26 1.0(3) . . . . ?
C24 C25 C26 C21 1.1(3) . . . . ?
C22 C21 C26 C25 -2.2(3) . . . . ?
C2 C21 C26 C25 178.29(19) . . . . ?
C6 N1 C27 C28 -173.62(17) . . . . ?
B1 N1 C27 C28 6.8(3) . . . . ?
N1 C27 C28 C33 -174.92(18) . . . . ?
N1 C27 C28 C29 10.1(3) . . . . ?
B1 O1 C29 C30 161.56(17) . . . . ?
B1 O1 C29 C28 -21.9(3) . . . . ?
C33 C28 C29 O1 -178.26(17) . . . . ?
C27 C28 C29 O1 -3.3(3) . . . . ?
C33 C28 C29 C30 -1.7(3) . . . . ?
C27 C28 C29 C30 173.34(17) . . . . ?
O1 C29 C30 C31 179.33(17) . . . . ?
C28 C29 C30 C31 2.7(3) . . . . ?
O1 C29 C30 I1 -1.8(2) . . . . ?
C28 C29 C30 I1 -178.39(13) . . . . ?
C29 C30 C31 C32 -1.4(3) . . . . ?
I1 C30 C31 C32 179.74(14) . . . . ?
C30 C31 C32 C33 -1.1(3) . . . . ?
C30 C31 C32 I2 179.52(14) . . . . ?
C31 C32 C33 C28 2.1(3) . . . . ?
I2 C32 C33 C28 -178.49(14) . . . . ?
C29 C28 C33 C32 -0.7(3) . . . . ?
C27 C28 C33 C32 -175.64(18) . . . . ?
C29 O1 B1 F1 155.57(16) . . . . ?
C29 O1 B1 F2 -81.9(2) . . . . ?
C29 O1 B1 N1 35.4(2) . . . . ?
C27 N1 B1 F1 -148.22(17) . . . . ?
C6 N1 B1 F1 32.2(2) . . . . ?
C27 N1 B1 F2 92.0(2) . . . . ?
C6 N1 B1 F2 -87.7(2) . . . . ?
C27 N1 B1 O1 -27.9(2) . . . . ?
C6 N1 B1 O1 152.44(16) . . . . ?

_refine_diff_density_max         0.728
_refine_diff_density_min         -0.678
_refine_diff_density_rms         0.142

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_2c-MCGG-BRM
_database_code_depnum_ccdc_archive 'CCDC 2075069'
loop_
_audit_author_name
_audit_author_address
'Ruben A. Toscano'
;Institute of Chemistry, UNAM
Mexico
;
_audit_update_record             
;
2021-04-02 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;
_audit_creation_date             2020-07-21
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          418-419
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H29 I2 N O2'
_chemical_formula_weight         761.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.330(3)
_cell_length_b                   12.726(3)
_cell_length_c                   15.427(3)
_cell_angle_alpha                72.271(10)
_cell_angle_beta                 76.816(12)
_cell_angle_gamma                70.156(10)
_cell_volume                     1625.2(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9967
_cell_measurement_theta_min      3.04
_cell_measurement_theta_max      68.33

_exptl_crystal_description       Prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_F_000             748
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.355
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.106
_exptl_absorpt_coefficient_mu    15.437
_shelx_estimated_absorpt_T_min   0.073
_shelx_estimated_absorpt_T_max   0.291
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1706
_exptl_absorpt_correction_T_max  0.4672
_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      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            20040
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.037
_diffrn_reflns_theta_max         68.178
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5926
_reflns_number_gt                4511
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0546P)²+2.1423P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5926
_refine_ls_number_parameters     374
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1304
_refine_ls_wR_factor_gt          0.1183
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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
I1 I 0.90108(5) 0.49209(4) 1.21177(2) 0.07173(16) Uani 1 1 d . . . . .
I2 I 0.39962(7) 0.85038(4) 1.00749(3) 0.0953(2) Uani 1 1 d . . . . .
O1 O 0.5080(6) 0.6658(4) 0.8922(3) 0.0721(12) Uani 1 1 d . . . . .
H1 H 0.533(7) 0.627(6) 0.863(5) 0.108 Uiso 1 1 calc R U . . .
O2 O 1.0565(19) 0.1715(13) 0.0047(10) 0.276(8) Uani 1 1 d . . . . .
N1 N 0.6641(5) 0.4806(4) 0.8397(3) 0.0532(10) Uani 1 1 d . . . . .
C1 C 0.7756(6) 0.2650(4) 0.5457(3) 0.0453(11) Uani 1 1 d . . . . .
C2 C 0.6730(6) 0.2206(4) 0.5323(3) 0.0436(10) Uani 1 1 d . . . . .
C3 C 0.7462(5) 0.3155(4) 0.6266(3) 0.0437(10) Uani 1 1 d . . . . .
C4 C 0.6177(6) 0.4074(4) 0.6374(4) 0.0526(12) Uani 1 1 d . . . . .
H4 H 0.546920 0.435742 0.595969 0.063 Uiso 1 1 calc R U . . .
C5 C 0.5934(6) 0.4578(5) 0.7100(4) 0.0544(12) Uani 1 1 d . . . . .
H5 H 0.506300 0.519518 0.716533 0.065 Uiso 1 1 calc R U . . .
C6 C 0.6967(6) 0.4175(4) 0.7722(3) 0.0475(11) Uani 1 1 d . . . . .
C7 C 0.8260(6) 0.3248(5) 0.7621(3) 0.0542(12) Uani 1 1 d . . . . .
H7 H 0.895869 0.295520 0.804093 0.065 Uiso 1 1 calc R U . . .
C8 C 0.8498(6) 0.2766(4) 0.6891(3) 0.0494(11) Uani 1 1 d . . . . .
H8 H 0.938183 0.216074 0.681748 0.059 Uiso 1 1 calc R U . . .
C9 C 0.9230(6) 0.2725(4) 0.4833(3) 0.0463(11) Uani 1 1 d . . . . .
C10 C 1.0222(7) 0.1799(5) 0.4500(4) 0.0668(15) Uani 1 1 d . . . . .
H10 H 0.997551 0.110929 0.465667 0.080 Uiso 1 1 calc R U . . .
C11 C 1.1601(8) 0.1900(7) 0.3924(5) 0.081(2) Uani 1 1 d . . . . .
H11 H 1.226118 0.127869 0.369885 0.098 Uiso 1 1 calc R U . . .
C12 C 1.1972(8) 0.2914(8) 0.3695(5) 0.083(2) Uani 1 1 d . . . . .
H12 H 1.288080 0.297958 0.331116 0.099 Uiso 1 1 calc R U . . .
C13 C 1.1017(8) 0.3825(7) 0.4026(4) 0.0724(18) Uani 1 1 d . . . . .
H13 H 1.127871 0.450924 0.387217 0.087 Uiso 1 1 calc R U . . .
C14 C 0.9647(7) 0.3735(5) 0.4595(3) 0.0571(13) Uani 1 1 d . . . . .
H14 H 0.900273 0.436205 0.481897 0.069 Uiso 1 1 calc R U . . .
C15 C 0.6769(6) 0.1887(4) 0.4458(3) 0.0437(10) Uani 1 1 d . . . . .
C16 C 0.6450(7) 0.0873(5) 0.4499(4) 0.0607(14) Uani 1 1 d . . . . .
H16 H 0.628013 0.036690 0.506433 0.073 Uiso 1 1 calc R U . . .
C17 C 0.6389(8) 0.0624(5) 0.3694(4) 0.0741(18) Uani 1 1 d . . . . .
H17 H 0.619493 -0.005746 0.372387 0.089 Uiso 1 1 calc R U . . .
C18 C 0.6610(8) 0.1370(6) 0.2856(4) 0.0699(16) Uani 1 1 d . . . . .
H18 H 0.654311 0.120536 0.232130 0.084 Uiso 1 1 calc R U . . .
C19 C 0.6931(7) 0.2365(5) 0.2811(4) 0.0638(15) Uani 1 1 d . . . . .
H19 H 0.709766 0.286791 0.224343 0.077 Uiso 1 1 calc R U . . .
C20 C 0.7006(7) 0.2620(4) 0.3601(3) 0.0543(13) Uani 1 1 d . . . . .
H20 H 0.722083 0.329683 0.355966 0.065 Uiso 1 1 calc R U . . .
C21 C 0.5383(6) 0.2055(4) 0.6041(3) 0.0482(12) Uani 1 1 d . . . . .
C22 C 0.5577(7) 0.1384(5) 0.6921(4) 0.0622(15) Uani 1 1 d . . . . .
H22 H 0.656252 0.100336 0.707613 0.075 Uiso 1 1 calc R U . . .
C23 C 0.4291(10) 0.1274(6) 0.7583(4) 0.079(2) Uani 1 1 d . . . . .
H23 H 0.442236 0.081710 0.817375 0.095 Uiso 1 1 calc R U . . .
C24 C 0.2845(9) 0.1842(7) 0.7355(5) 0.083(2) Uani 1 1 d . . . . .
H24 H 0.199242 0.177492 0.779458 0.099 Uiso 1 1 calc R U . . .
C25 C 0.2644(9) 0.2499(7) 0.6499(6) 0.085(2) Uani 1 1 d . . . . .
H25 H 0.165396 0.288892 0.635427 0.102 Uiso 1 1 calc R U . . .
C26 C 0.3890(7) 0.2597(5) 0.5838(4) 0.0626(14) Uani 1 1 d . . . . .
H26 H 0.373159 0.303374 0.524432 0.075 Uiso 1 1 calc R U . . .
C27 C 0.7373(7) 0.4462(5) 0.9085(3) 0.0556(13) Uani 1 1 d . . . . .
H27 H 0.810482 0.374289 0.918161 0.067 Uiso 1 1 calc R U . . .
C28 C 0.7079(7) 0.5184(5) 0.9723(3) 0.0547(13) Uani 1 1 d . . . . .
C29 C 0.7953(7) 0.4806(5) 1.0443(4) 0.0578(13) Uani 1 1 d . . . . .
H29 H 0.871411 0.410072 1.051791 0.069 Uiso 1 1 calc R U . . .
C30 C 0.7676(7) 0.5489(5) 1.1042(3) 0.0582(14) Uani 1 1 d . . . . .
C31 C 0.6551(7) 0.6537(5) 1.0952(3) 0.0597(14) Uani 1 1 d . . . . .
H31 H 0.637441 0.698555 1.136339 0.072 Uiso 1 1 calc R U . . .
C32 C 0.5699(7) 0.6905(5) 1.0241(4) 0.0590(14) Uani 1 1 d . . . . .
C33 C 0.5933(7) 0.6244(5) 0.9610(3) 0.0564(13) Uani 1 1 d . . . . .
C34 C 1.0658(16) 0.1252(12) 0.0822(11) 0.145(4) Uani 1 1 d . . . . .
C35 C 1.0155(15) 0.0251(10) 0.1314(10) 0.182(6) Uani 1 1 d . . . . .
H35A H 1.049811 -0.029991 0.094719 0.273 Uiso 1 1 calc R U . . .
H35B H 0.905249 0.047381 0.144189 0.273 Uiso 1 1 calc R U . . .
H35C H 1.058061 -0.008812 0.188154 0.273 Uiso 1 1 calc R U . . .
C36 C 1.1396(15) 0.1689(12) 0.1340(10) 0.176(6) Uani 1 1 d . . . . .
H36A H 1.249357 0.142962 0.118479 0.264 Uiso 1 1 calc R U . . .
H36B H 1.111942 0.140350 0.198738 0.264 Uiso 1 1 calc R U . . .
H36C H 1.105264 0.251669 0.118213 0.264 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
I1 C30 2.105(6) . ?
I2 C32 2.098(6) . ?
O1 C33 1.340(7) . ?
O2 C34 1.170(15) . ?
N1 C27 1.275(7) . ?
N1 C6 1.421(6) . ?
C1 C2 1.345(7) . ?
C1 C3 1.502(6) . ?
C1 C9 1.503(7) . ?
C2 C21 1.497(7) . ?
C2 C15 1.498(6) . ?
C3 C4 1.382(7) . ?
C3 C8 1.385(7) . ?
C4 C5 1.393(7) . ?
C5 C6 1.378(7) . ?
C6 C7 1.390(8) . ?
C7 C8 1.381(7) . ?
C9 C10 1.386(8) . ?
C9 C14 1.387(7) . ?
C10 C11 1.408(9) . ?
C11 C12 1.371(10) . ?
C12 C13 1.360(10) . ?
C13 C14 1.395(8) . ?
C15 C20 1.386(7) . ?
C15 C16 1.400(6) . ?
C16 C17 1.390(8) . ?
C17 C18 1.371(9) . ?
C18 C19 1.375(8) . ?
C19 C20 1.375(7) . ?
C21 C22 1.381(7) . ?
C21 C26 1.389(8) . ?
C22 C23 1.403(9) . ?
C23 C24 1.366(11) . ?
C24 C25 1.345(11) . ?
C25 C26 1.375(9) . ?
C27 C28 1.465(7) . ?
C28 C29 1.397(8) . ?
C28 C33 1.399(8) . ?
C29 C30 1.380(7) . ?
C30 C31 1.380(8) . ?
C31 C32 1.373(8) . ?
C32 C33 1.408(7) . ?
C34 C35 1.440(16) . ?
C34 C36 1.483(18) . ?

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
C27 N1 C6 123.0(5) . . ?
C2 C1 C3 120.7(4) . . ?
C2 C1 C9 125.1(4) . . ?
C3 C1 C9 114.2(4) . . ?
C1 C2 C21 120.6(4) . . ?
C1 C2 C15 124.5(4) . . ?
C21 C2 C15 114.9(4) . . ?
C4 C3 C8 118.1(4) . . ?
C4 C3 C1 120.1(4) . . ?
C8 C3 C1 121.7(5) . . ?
C3 C4 C5 120.4(5) . . ?
C6 C5 C4 120.9(5) . . ?
C5 C6 C7 119.1(4) . . ?
C5 C6 N1 115.6(5) . . ?
C7 C6 N1 125.3(5) . . ?
C8 C7 C6 119.5(5) . . ?
C7 C8 C3 122.0(5) . . ?
C10 C9 C14 118.2(5) . . ?
C10 C9 C1 121.9(5) . . ?
C14 C9 C1 119.8(5) . . ?
C9 C10 C11 120.2(6) . . ?
C12 C11 C10 120.1(7) . . ?
C13 C12 C11 120.3(6) . . ?
C12 C13 C14 120.1(6) . . ?
C9 C14 C13 121.1(6) . . ?
C20 C15 C16 118.1(4) . . ?
C20 C15 C2 121.4(4) . . ?
C16 C15 C2 120.3(4) . . ?
C17 C16 C15 119.9(5) . . ?
C18 C17 C16 120.8(5) . . ?
C17 C18 C19 119.5(5) . . ?
C20 C19 C18 120.4(5) . . ?
C19 C20 C15 121.3(5) . . ?
C22 C21 C26 117.9(5) . . ?
C22 C21 C2 121.6(5) . . ?
C26 C21 C2 120.5(5) . . ?
C21 C22 C23 120.2(6) . . ?
C24 C23 C22 119.7(6) . . ?
C25 C24 C23 120.5(6) . . ?
C24 C25 C26 120.5(8) . . ?
C25 C26 C21 121.1(6) . . ?
N1 C27 C28 121.0(6) . . ?
C29 C28 C33 120.4(5) . . ?
C29 C28 C27 119.5(6) . . ?
C33 C28 C27 120.1(5) . . ?
C30 C29 C28 119.4(6) . . ?
C29 C30 C31 121.7(5) . . ?
C29 C30 I1 119.2(5) . . ?
C31 C30 I1 119.1(4) . . ?
C32 C31 C30 118.6(5) . . ?
C31 C32 C33 122.1(6) . . ?
C31 C32 I2 119.6(4) . . ?
C33 C32 I2 118.3(4) . . ?
O1 C33 C28 122.9(5) . . ?
O1 C33 C32 119.3(5) . . ?
C28 C33 C32 117.8(5) . . ?
O2 C34 C35 124.8(18) . . ?
O2 C34 C36 118.5(15) . . ?
C35 C34 C36 116.7(14) . . ?

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
C3 C1 C2 C21 -8.5(7) . . . . ?
C9 C1 C2 C21 173.2(5) . . . . ?
C3 C1 C2 C15 168.1(4) . . . . ?
C9 C1 C2 C15 -10.2(8) . . . . ?
C2 C1 C3 C4 -59.7(6) . . . . ?
C9 C1 C3 C4 118.7(5) . . . . ?
C2 C1 C3 C8 124.0(5) . . . . ?
C9 C1 C3 C8 -57.6(6) . . . . ?
C8 C3 C4 C5 -0.7(7) . . . . ?
C1 C3 C4 C5 -177.1(5) . . . . ?
C3 C4 C5 C6 0.1(8) . . . . ?
C4 C5 C6 C7 -0.4(8) . . . . ?
C4 C5 C6 N1 176.3(5) . . . . ?
C27 N1 C6 C5 171.1(5) . . . . ?
C27 N1 C6 C7 -12.5(8) . . . . ?
C5 C6 C7 C8 1.3(7) . . . . ?
N1 C6 C7 C8 -175.1(5) . . . . ?
C6 C7 C8 C3 -1.9(8) . . . . ?
C4 C3 C8 C7 1.6(7) . . . . ?
C1 C3 C8 C7 178.0(4) . . . . ?
C2 C1 C9 C10 -46.5(8) . . . . ?
C3 C1 C9 C10 135.1(5) . . . . ?
C2 C1 C9 C14 135.1(5) . . . . ?
C3 C1 C9 C14 -43.3(6) . . . . ?
C14 C9 C10 C11 -0.9(9) . . . . ?
C1 C9 C10 C11 -179.3(5) . . . . ?
C9 C10 C11 C12 0.3(10) . . . . ?
C10 C11 C12 C13 0.4(11) . . . . ?
C11 C12 C13 C14 -0.5(10) . . . . ?
C10 C9 C14 C13 0.8(8) . . . . ?
C1 C9 C14 C13 179.3(5) . . . . ?
C12 C13 C14 C9 -0.1(9) . . . . ?
C1 C2 C15 C20 -45.9(7) . . . . ?
C21 C2 C15 C20 130.9(5) . . . . ?
C1 C2 C15 C16 138.9(6) . . . . ?
C21 C2 C15 C16 -44.3(7) . . . . ?
C20 C15 C16 C17 0.4(9) . . . . ?
C2 C15 C16 C17 175.7(6) . . . . ?
C15 C16 C17 C18 -1.2(10) . . . . ?
C16 C17 C18 C19 1.5(11) . . . . ?
C17 C18 C19 C20 -1.0(10) . . . . ?
C18 C19 C20 C15 0.2(9) . . . . ?
C16 C15 C20 C19 0.1(8) . . . . ?
C2 C15 C20 C19 -175.2(5) . . . . ?
C1 C2 C21 C22 -58.6(7) . . . . ?
C15 C2 C21 C22 124.4(5) . . . . ?
C1 C2 C21 C26 121.0(5) . . . . ?
C15 C2 C21 C26 -55.9(6) . . . . ?
C26 C21 C22 C23 -0.7(7) . . . . ?
C2 C21 C22 C23 179.0(5) . . . . ?
C21 C22 C23 C24 -0.6(9) . . . . ?
C22 C23 C24 C25 0.5(10) . . . . ?
C23 C24 C25 C26 0.8(10) . . . . ?
C24 C25 C26 C21 -2.1(10) . . . . ?
C22 C21 C26 C25 2.0(8) . . . . ?
C2 C21 C26 C25 -177.7(5) . . . . ?
C6 N1 C27 C28 175.1(4) . . . . ?
N1 C27 C28 C29 -176.9(5) . . . . ?
N1 C27 C28 C33 2.9(8) . . . . ?
C33 C28 C29 C30 0.0(8) . . . . ?
C27 C28 C29 C30 179.8(5) . . . . ?
C28 C29 C30 C31 0.3(8) . . . . ?
C28 C29 C30 I1 -179.4(4) . . . . ?
C29 C30 C31 C32 -0.4(8) . . . . ?
I1 C30 C31 C32 179.3(4) . . . . ?
C30 C31 C32 C33 0.3(8) . . . . ?
C30 C31 C32 I2 -179.3(4) . . . . ?
C29 C28 C33 O1 178.8(5) . . . . ?
C27 C28 C33 O1 -1.1(8) . . . . ?
C29 C28 C33 C32 -0.1(8) . . . . ?
C27 C28 C33 C32 -179.9(5) . . . . ?
C31 C32 C33 O1 -179.0(5) . . . . ?
I2 C32 C33 O1 0.7(7) . . . . ?
C31 C32 C33 C28 -0.1(8) . . . . ?
I2 C32 C33 C28 179.5(4) . . . . ?

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
O1 H1 N1 0.71 1.94 2.574(6) 148.4 . yes
C35 H35A I2 0.96 3.26 3.936(11) 128.8 1_644 yes

_refine_diff_density_max         1.248
_refine_diff_density_min         -0.921
_refine_diff_density_rms         0.087


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
