# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

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

data_03534_grande
_database_code_depnum_ccdc_archive 'CCDC 2191020'
loop_
_audit_author_name
_audit_author_address
'Josefina Perles Hernaez'
;Servicio Interdepartamental de Investigacion (UAM)
Spain
;
_audit_update_record             
;
2022-07-18 deposited with the CCDC.	2023-01-13 downloaded from the CCDC.
;
_chemical_name_systematic        
'(1R,2S,3R)-2-methyl-3-(1-methyl-1H-indol-5-yl)-2-phenylcyclopropyl 3,5-dibromobenzoate'
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H21 Br2 N O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         539.26
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.6562(7)
_cell_length_b                   23.5435(18)
_cell_length_c                   11.2698(9)
_cell_angle_alpha                90
_cell_angle_beta                 97.609(4)
_cell_angle_gamma                90
_cell_volume                     2276.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9045
_cell_measurement_theta_min      2.9264
_cell_measurement_theta_max      20.7894
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.256
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.124
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1080

_exptl_absorpt_coefficient_mu    3.584
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.56
_exptl_absorpt_correction_T_max  0.67

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   'sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            73125
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_theta_min         3.17
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       13

_refine_special_details          
;
;

_reflns_number_total             8334
_reflns_number_gt                6626
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0319
_refine_ls_wR_factor_gt          0.0627
_refine_ls_wR_factor_ref         0.0698
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_number_reflns         8334
_refine_ls_number_parameters     563
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0272P)²+1.1307P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.441
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 2732 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.006(3)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service v2010.9.0.0'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1328)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.1918(6) 0.4084(2) 0.6100(5) 0.0438(13) Uani d . . . 1 . .
H H1 0.265873 0.380694 0.649744 0.053000 Uiso calc U . R 1 . .
C C2 0.2006(6) 0.4182(2) 0.4796(4) 0.0402(12) Uani d . . . 1 . .
C C3 0.2596(7) 0.4622(2) 0.5743(5) 0.0428(13) Uani d . . . 1 . .
H H3 0.373587 0.462547 0.591617 0.051000 Uiso calc U . R 1 . .
C C4 -0.0167(7) 0.3612(2) 0.6812(5) 0.0483(13) Uani d . . . 1 . .
C C5 -0.1632(6) 0.3700(2) 0.7333(4) 0.0440(13) Uani d . . . 1 . .
C C6 -0.2211(6) 0.4239(2) 0.7497(5) 0.0455(13) Uani d . . . 1 . .
H H6 -0.171608 0.455785 0.723869 0.055000 Uiso calc U . R 1 . .
C C7 -0.3529(6) 0.4295(2) 0.8047(5) 0.0508(14) Uani d . . . 1 . .
C C8 -0.4297(7) 0.3840(3) 0.8417(5) 0.0599(16) Uani d . . . 1 . .
H H8 -0.518165 0.388728 0.879273 0.072000 Uiso calc U . R 1 . .
C C9 -0.3734(8) 0.3303(3) 0.8222(5) 0.0593(16) Uani d . . . 1 . .
C C10 -0.2414(7) 0.3227(2) 0.7689(5) 0.0514(15) Uani d . . . 1 . .
H H10 -0.204671 0.286327 0.756739 0.062000 Uiso calc U . R 1 . .
C C11 0.1907(6) 0.5206(2) 0.5780(5) 0.0428(12) Uani d . . . 1 . .
C C12 0.0797(6) 0.5355(2) 0.6493(5) 0.0445(13) Uani d . . . 1 . .
H H12 0.038563 0.508165 0.695703 0.053000 Uiso calc U . R 1 . .
C C13 0.0287(6) 0.5921(2) 0.6518(5) 0.0415(12) Uani d . . . 1 . .
C C14 -0.0780(7) 0.6215(2) 0.7153(5) 0.0534(14) Uani d . . . 1 . .
H H14 -0.141173 0.605530 0.766992 0.064000 Uiso calc U . R 1 . .
C C15 -0.0709(8) 0.6764(3) 0.6870(6) 0.0636(17) Uani d . . . 1 . .
H H15 -0.128894 0.704955 0.717019 0.076000 Uiso calc U . R 1 . .
C C16 0.0952(6) 0.6328(2) 0.5834(5) 0.0450(13) Uani d . . . 1 . .
C C17 0.2045(6) 0.6182(2) 0.5108(5) 0.0503(14) Uani d . . . 1 . .
H H17 0.247416 0.645583 0.465364 0.060000 Uiso calc U . R 1 . .
C C18 0.2489(6) 0.5625(2) 0.5069(5) 0.0479(14) Uani d . . . 1 . .
H H18 0.319776 0.552013 0.455638 0.057000 Uiso calc U . R 1 . .
C C19 0.0746(9) 0.7387(3) 0.5579(7) 0.082(2) Uani d . . . 1 . .
H H19A 0.070845 0.735321 0.472666 0.123000 Uiso calc U . R 1 . .
H H19B 0.177790 0.749415 0.592419 0.123000 Uiso calc U . R 1 . .
H H19C 0.001659 0.767113 0.575922 0.123000 Uiso calc U . R 1 . .
C C20 0.3217(6) 0.3856(2) 0.4226(5) 0.0403(12) Uani d . . . 1 . .
C C21 0.4645(6) 0.3713(2) 0.4860(5) 0.0469(14) Uani d . . . 1 . .
H H21 0.486712 0.381609 0.566054 0.056000 Uiso calc U . R 1 . .
C C22 0.5741(7) 0.3420(3) 0.4324(6) 0.0592(17) Uani d . . . 1 . .
H H22 0.669594 0.333022 0.476267 0.071000 Uiso calc U . R 1 . .
C C23 0.5439(9) 0.3262(3) 0.3162(7) 0.0707(19) Uani d . . . 1 . .
H H23 0.618286 0.306181 0.280612 0.085000 Uiso calc U . R 1 . .
C C24 0.4059(10) 0.3395(3) 0.2519(6) 0.083(2) Uani d . . . 1 . .
H H24 0.385423 0.328670 0.172023 0.099000 Uiso calc U . R 1 . .
C C25 0.2944(8) 0.3692(3) 0.3043(5) 0.0682(19) Uani d . . . 1 . .
H H25 0.199841 0.378230 0.259044 0.082000 Uiso calc U . R 1 . .
C C26 0.0507(7) 0.4313(2) 0.4029(5) 0.0564(15) Uani d . . . 1 . .
H H26A 0.071058 0.454507 0.336611 0.085000 Uiso calc U . R 1 . .
H H26B -0.017170 0.451314 0.449266 0.085000 Uiso calc U . R 1 . .
H H26C 0.001805 0.396564 0.373355 0.085000 Uiso calc U . R 1 . .
Br Br1 -0.42552(8) 0.50362(3) 0.83431(8) 0.0837(2) Uani d . . . 1 . .
Br Br2 -0.47586(10) 0.26600(3) 0.87656(8) 0.0939(3) Uani d . . . 1 . .
N N1 0.0345(6) 0.68475(19) 0.6071(4) 0.0560(13) Uani d . . . 1 . .
O O1 0.0446(4) 0.41030(14) 0.6509(3) 0.0501(9) Uani d . . . 1 . .
O O2 0.0447(6) 0.31601(17) 0.6731(5) 0.0791(14) Uani d . . . 1 . .
C C27 1.0990(6) 0.5967(2) 0.0440(5) 0.0419(12) Uani d . . . 1 . .
H H27 1.075032 0.630909 -0.004427 0.050000 Uiso calc U . R 1 . .
C C28 1.2652(6) 0.5772(2) 0.0564(4) 0.0419(12) Uani d . . . 1 . .
C C29 1.1343(6) 0.5452(2) -0.0228(4) 0.0419(13) Uani d . . . 1 . .
H H29 1.135220 0.552987 -0.108183 0.050000 Uiso calc U . R 1 . .
C C30 0.9943(6) 0.6347(2) 0.2081(5) 0.0460(13) Uani d . . . 1 . .
C C31 0.8755(6) 0.6258(2) 0.2910(4) 0.0394(12) Uani d . . . 1 . .
C C32 0.8288(6) 0.5713(2) 0.3192(5) 0.0407(12) Uani d . . . 1 . .
H H32 0.871700 0.539549 0.286999 0.049000 Uiso calc U . R 1 . .
C C33 0.7189(6) 0.5654(2) 0.3950(5) 0.0457(13) Uani d . . . 1 . .
C C34 0.6529(6) 0.6125(3) 0.4436(5) 0.0528(15) Uani d . . . 1 . .
H H34 0.579182 0.608256 0.495952 0.063000 Uiso calc U . R 1 . .
C C35 0.6995(7) 0.6651(2) 0.4123(5) 0.0527(15) Uani d . . . 1 . .
C C36 0.8097(6) 0.6728(2) 0.3375(5) 0.0474(13) Uani d . . . 1 . .
H H36 0.840007 0.709216 0.318238 0.057000 Uiso calc U . R 1 . .
C C37 1.0900(6) 0.4851(2) -0.0007(4) 0.0423(12) Uani d . . . 1 . .
C C38 0.9628(7) 0.4700(2) 0.0528(4) 0.0458(13) Uani d . . . 1 . .
H H38 0.899716 0.497889 0.079472 0.055000 Uiso calc U . R 1 . .
C C39 0.9278(7) 0.4127(2) 0.0671(5) 0.0536(15) Uani d . . . 1 . .
C C40 0.8139(9) 0.3824(3) 0.1187(6) 0.074(2) Uani d . . . 1 . .
H H40 0.733716 0.397638 0.156001 0.089000 Uiso calc U . R 1 . .
C C41 0.8439(10) 0.3261(3) 0.1035(7) 0.082(2) Uani d . . . 1 . .
H H41 0.783760 0.296661 0.127975 0.099000 Uiso calc U . R 1 . .
C C42 1.0265(8) 0.3721(2) 0.0251(5) 0.0531(15) Uani d . . . 1 . .
C C43 1.1536(8) 0.3862(3) -0.0301(5) 0.0626(17) Uani d . . . 1 . .
H H43 1.216715 0.358529 -0.057933 0.075000 Uiso calc U . R 1 . .
C C44 1.1830(7) 0.4432(2) -0.0421(5) 0.0554(15) Uani d . . . 1 . .
H H44 1.267927 0.454203 -0.079307 0.066000 Uiso calc U . R 1 . .
C C45 1.0355(11) 0.2653(3) 0.0149(8) 0.101(3) Uani d . . . 1 . .
H H45A 1.140243 0.261400 0.054371 0.152000 Uiso calc U . R 1 . .
H H45B 1.035861 0.264395 -0.070243 0.152000 Uiso calc U . R 1 . .
H H45C 0.973092 0.234512 0.038129 0.152000 Uiso calc U . R 1 . .
C C46 1.3752(6) 0.6123(2) -0.0062(5) 0.0432(12) Uani d . . . 1 . .
C C47 1.3290(7) 0.6373(2) -0.1159(5) 0.0547(15) Uani d . . . 1 . .
H H47 1.226416 0.633296 -0.151610 0.066000 Uiso calc U . R 1 . .
C C48 1.4323(9) 0.6679(3) -0.1732(6) 0.0666(18) Uani d . . . 1 . .
H H48 1.398268 0.684250 -0.247124 0.080000 Uiso calc U . R 1 . .
C C49 1.5818(9) 0.6746(3) -0.1245(7) 0.0681(18) Uani d . . . 1 . .
H H49 1.650694 0.695149 -0.164555 0.082000 Uiso calc U . R 1 . .
C C50 1.6300(7) 0.6513(3) -0.0172(7) 0.0705(19) Uani d . . . 1 . .
H H50 1.732737 0.656221 0.017484 0.085000 Uiso calc U . R 1 . .
C C51 1.5285(7) 0.6199(3) 0.0427(5) 0.0570(15) Uani d . . . 1 . .
H H51 1.564304 0.603733 0.116556 0.068000 Uiso calc U . R 1 . .
C C52 1.3279(8) 0.5478(3) 0.1723(5) 0.0615(16) Uani d . . . 1 . .
H H52A 1.412968 0.523465 0.158969 0.092000 Uiso calc U . R 1 . .
H H52B 1.246727 0.525482 0.199628 0.092000 Uiso calc U . R 1 . .
H H52C 1.363751 0.575702 0.231662 0.092000 Uiso calc U . R 1 . .
Br Br3 0.65033(7) 0.49195(2) 0.43177(6) 0.06694(19) Uani d . . . 1 . .
Br Br4 0.60586(9) 0.72948(3) 0.47428(7) 0.0817(2) Uani d . . . 1 . .
N N2 0.9714(7) 0.3184(2) 0.0485(5) 0.0679(15) Uani d . . . 1 . .
O O3 1.0099(4) 0.58900(14) 0.1404(3) 0.0500(9) Uani d . . . 1 . .
O O4 1.0640(5) 0.67789(16) 0.2000(4) 0.0677(12) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 . 1.412(6) ?
C1 C3 . 1.474(7) ?
C1 C2 . 1.499(7) ?
C2 C26 . 1.493(8) ?
C2 C20 . 1.510(7) ?
C2 C3 . 1.527(7) ?
C3 C11 . 1.502(7) ?
C4 O2 . 1.198(6) ?
C4 O1 . 1.334(6) ?
C4 C5 . 1.481(8) ?
C5 C6 . 1.385(7) ?
C5 C10 . 1.391(7) ?
C6 C7 . 1.375(8) ?
C7 C8 . 1.355(8) ?
C7 Br1 . 1.900(5) ?
C8 C9 . 1.383(9) ?
C9 C10 . 1.371(8) ?
C9 Br2 . 1.896(6) ?
C11 C12 . 1.377(7) ?
C11 C18 . 1.405(7) ?
C12 C13 . 1.404(7) ?
C13 C16 . 1.401(7) ?
C13 C14 . 1.422(8) ?
C14 C15 . 1.333(9) ?
C15 N1 . 1.378(8) ?
C16 N1 . 1.371(7) ?
C16 C17 . 1.374(8) ?
C17 C18 . 1.370(8) ?
C19 N1 . 1.446(8) ?
C20 C25 . 1.377(8) ?
C20 C21 . 1.385(7) ?
C21 C22 . 1.375(8) ?
C22 C23 . 1.353(9) ?
C23 C24 . 1.350(10) ?
C24 C25 . 1.386(9) ?
C27 O3 . 1.425(6) ?
C27 C29 . 1.479(7) ?
C27 C28 . 1.498(7) ?
C28 C46 . 1.505(7) ?
C28 C52 . 1.514(7) ?
C28 C29 . 1.543(7) ?
C29 C37 . 1.497(7) ?
C30 O4 . 1.193(6) ?
C30 O3 . 1.335(6) ?
C30 C31 . 1.493(7) ?
C31 C36 . 1.379(7) ?
C31 C32 . 1.394(7) ?
C32 C33 . 1.368(7) ?
C33 C34 . 1.392(8) ?
C33 Br3 . 1.893(5) ?
C34 C35 . 1.362(9) ?
C35 C36 . 1.367(8) ?
C35 Br4 . 1.895(5) ?
C37 C38 . 1.370(7) ?
C37 C44 . 1.391(7) ?
C38 C39 . 1.395(7) ?
C39 C40 . 1.405(9) ?
C39 C42 . 1.406(9) ?
C40 C41 . 1.366(10) ?
C41 N2 . 1.347(9) ?
C42 C43 . 1.374(9) ?
C42 N2 . 1.389(7) ?
C43 C44 . 1.378(8) ?
C45 N2 . 1.440(9) ?
C46 C51 . 1.379(7) ?
C46 C47 . 1.379(8) ?
C47 C48 . 1.374(8) ?
C48 C49 . 1.346(9) ?
C49 C50 . 1.343(9) ?
C50 C51 . 1.390(8) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C1 C3 . . 118.1(4) ?
O1 C1 C2 . . 118.7(5) ?
C3 C1 C2 . . 61.8(3) ?
C26 C2 C1 . . 116.5(5) ?
C26 C2 C20 . . 117.2(4) ?
C1 C2 C20 . . 117.8(4) ?
C26 C2 C3 . . 116.7(4) ?
C1 C2 C3 . . 58.3(3) ?
C20 C2 C3 . . 117.1(5) ?
C1 C3 C11 . . 127.3(4) ?
C1 C3 C2 . . 59.9(3) ?
C11 C3 C2 . . 122.9(5) ?
O2 C4 O1 . . 123.7(5) ?
O2 C4 C5 . . 124.5(5) ?
O1 C4 C5 . . 111.7(5) ?
C6 C5 C10 . . 119.8(5) ?
C6 C5 C4 . . 121.7(5) ?
C10 C5 C4 . . 118.5(5) ?
C7 C6 C5 . . 118.9(5) ?
C8 C7 C6 . . 122.2(5) ?
C8 C7 Br1 . . 119.1(4) ?
C6 C7 Br1 . . 118.7(4) ?
C7 C8 C9 . . 118.5(5) ?
C10 C9 C8 . . 121.3(6) ?
C10 C9 Br2 . . 119.4(5) ?
C8 C9 Br2 . . 119.3(5) ?
C9 C10 C5 . . 119.2(5) ?
C12 C11 C18 . . 119.0(5) ?
C12 C11 C3 . . 124.0(5) ?
C18 C11 C3 . . 116.9(4) ?
C11 C12 C13 . . 120.0(5) ?
C16 C13 C12 . . 119.0(5) ?
C16 C13 C14 . . 106.5(5) ?
C12 C13 C14 . . 134.4(5) ?
C15 C14 C13 . . 107.4(5) ?
C14 C15 N1 . . 110.5(5) ?
N1 C16 C17 . . 130.6(5) ?
N1 C16 C13 . . 107.9(5) ?
C17 C16 C13 . . 121.5(5) ?
C18 C17 C16 . . 118.4(5) ?
C17 C18 C11 . . 122.1(5) ?
C25 C20 C21 . . 117.3(5) ?
C25 C20 C2 . . 120.9(5) ?
C21 C20 C2 . . 121.8(5) ?
C22 C21 C20 . . 121.0(6) ?
C23 C22 C21 . . 120.5(6) ?
C24 C23 C22 . . 119.9(6) ?
C23 C24 C25 . . 120.4(7) ?
C20 C25 C24 . . 120.9(6) ?
C16 N1 C15 . . 107.7(5) ?
C16 N1 C19 . . 126.2(5) ?
C15 N1 C19 . . 126.1(5) ?
C4 O1 C1 . . 117.5(4) ?
O3 C27 C29 . . 117.0(4) ?
O3 C27 C28 . . 120.0(4) ?
C29 C27 C28 . . 62.4(3) ?
C27 C28 C46 . . 116.6(4) ?
C27 C28 C52 . . 116.8(5) ?
C46 C28 C52 . . 118.6(5) ?
C27 C28 C29 . . 58.2(3) ?
C46 C28 C29 . . 117.3(4) ?
C52 C28 C29 . . 115.3(5) ?
C27 C29 C37 . . 127.9(4) ?
C27 C29 C28 . . 59.4(3) ?
C37 C29 C28 . . 123.4(4) ?
O4 C30 O3 . . 123.5(5) ?
O4 C30 C31 . . 124.4(5) ?
O3 C30 C31 . . 112.0(4) ?
C36 C31 C32 . . 120.4(5) ?
C36 C31 C30 . . 118.6(5) ?
C32 C31 C30 . . 121.1(4) ?
C33 C32 C31 . . 118.8(5) ?
C32 C33 C34 . . 121.4(5) ?
C32 C33 Br3 . . 119.6(4) ?
C34 C33 Br3 . . 119.0(4) ?
C35 C34 C33 . . 118.1(5) ?
C34 C35 C36 . . 122.4(5) ?
C34 C35 Br4 . . 118.4(4) ?
C36 C35 Br4 . . 119.3(5) ?
C35 C36 C31 . . 119.0(5) ?
C38 C37 C44 . . 119.9(5) ?
C38 C37 C29 . . 123.9(5) ?
C44 C37 C29 . . 116.2(5) ?
C37 C38 C39 . . 120.1(5) ?
C38 C39 C40 . . 135.6(6) ?
C38 C39 C42 . . 117.8(5) ?
C40 C39 C42 . . 106.5(6) ?
C41 C40 C39 . . 106.6(7) ?
N2 C41 C40 . . 111.6(6) ?
C43 C42 N2 . . 128.4(6) ?
C43 C42 C39 . . 123.2(5) ?
N2 C42 C39 . . 108.4(6) ?
C42 C43 C44 . . 116.6(6) ?
C43 C44 C37 . . 122.4(6) ?
C51 C46 C47 . . 116.9(5) ?
C51 C46 C28 . . 121.2(5) ?
C47 C46 C28 . . 121.8(5) ?
C48 C47 C46 . . 121.0(6) ?
C49 C48 C47 . . 121.3(6) ?
C50 C49 C48 . . 119.1(6) ?
C49 C50 C51 . . 120.9(6) ?
C46 C51 C50 . . 120.8(6) ?
C41 N2 C42 . . 106.8(6) ?
C41 N2 C45 . . 127.2(6) ?
C42 N2 C45 . . 126.0(6) ?
C30 O3 C27 . . 116.1(4) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 C26 . . . . 2.0(7) ?
C3 C1 C2 C26 . . . . -106.4(5) ?
O1 C1 C2 C20 . . . . -145.4(5) ?
C3 C1 C2 C20 . . . . 106.3(5) ?
O1 C1 C2 C3 . . . . 108.3(5) ?
O1 C1 C3 C11 . . . . 1.0(8) ?
C2 C1 C3 C11 . . . . 110.4(6) ?
O1 C1 C3 C2 . . . . -109.4(5) ?
C26 C2 C3 C1 . . . . 106.1(5) ?
C20 C2 C3 C1 . . . . -107.5(5) ?
C26 C2 C3 C11 . . . . -11.2(7) ?
C1 C2 C3 C11 . . . . -117.3(5) ?
C20 C2 C3 C11 . . . . 135.2(5) ?
O2 C4 C5 C6 . . . . 174.3(6) ?
O1 C4 C5 C6 . . . . -1.8(8) ?
O2 C4 C5 C10 . . . . -4.2(9) ?
O1 C4 C5 C10 . . . . 179.7(5) ?
C10 C5 C6 C7 . . . . 2.1(8) ?
C4 C5 C6 C7 . . . . -176.4(5) ?
C5 C6 C7 C8 . . . . -1.1(9) ?
C5 C6 C7 Br1 . . . . 176.8(4) ?
C6 C7 C8 C9 . . . . -0.5(9) ?
Br1 C7 C8 C9 . . . . -178.4(5) ?
C7 C8 C9 C10 . . . . 1.2(9) ?
C7 C8 C9 Br2 . . . . 178.5(5) ?
C8 C9 C10 C5 . . . . -0.3(9) ?
Br2 C9 C10 C5 . . . . -177.6(4) ?
C6 C5 C10 C9 . . . . -1.4(8) ?
C4 C5 C10 C9 . . . . 177.1(5) ?
C1 C3 C11 C12 . . . . 21.7(9) ?
C2 C3 C11 C12 . . . . 96.8(7) ?
C1 C3 C11 C18 . . . . -160.7(5) ?
C2 C3 C11 C18 . . . . -85.7(6) ?
C18 C11 C12 C13 . . . . -1.2(8) ?
C3 C11 C12 C13 . . . . 176.3(5) ?
C11 C12 C13 C16 . . . . -1.6(8) ?
C11 C12 C13 C14 . . . . -178.3(6) ?
C16 C13 C14 C15 . . . . -1.3(7) ?
C12 C13 C14 C15 . . . . 175.7(6) ?
C13 C14 C15 N1 . . . . 0.5(7) ?
C12 C13 C16 N1 . . . . -175.9(5) ?
C14 C13 C16 N1 . . . . 1.6(6) ?
C12 C13 C16 C17 . . . . 2.4(9) ?
C14 C13 C16 C17 . . . . 180.0(5) ?
N1 C16 C17 C18 . . . . 177.6(6) ?
C13 C16 C17 C18 . . . . -0.4(8) ?
C16 C17 C18 C11 . . . . -2.5(9) ?
C12 C11 C18 C17 . . . . 3.3(9) ?
C3 C11 C18 C17 . . . . -174.3(5) ?
C26 C2 C20 C25 . . . . 0.5(8) ?
C1 C2 C20 C25 . . . . 147.7(6) ?
C3 C2 C20 C25 . . . . -145.7(5) ?
C26 C2 C20 C21 . . . . 180.0(5) ?
C1 C2 C20 C21 . . . . -32.9(7) ?
C3 C2 C20 C21 . . . . 33.7(7) ?
C25 C20 C21 C22 . . . . 0.1(8) ?
C2 C20 C21 C22 . . . . -179.4(5) ?
C20 C21 C22 C23 . . . . -0.4(8) ?
C21 C22 C23 C24 . . . . 0.5(10) ?
C22 C23 C24 C25 . . . . -0.1(12) ?
C21 C20 C25 C24 . . . . 0.2(10) ?
C2 C20 C25 C24 . . . . 179.7(6) ?
C23 C24 C25 C20 . . . . -0.2(12) ?
C17 C16 N1 C15 . . . . -179.5(6) ?
C13 C16 N1 C15 . . . . -1.3(7) ?
C17 C16 N1 C19 . . . . 0.1(10) ?
C13 C16 N1 C19 . . . . 178.3(6) ?
C14 C15 N1 C16 . . . . 0.5(7) ?
C14 C15 N1 C19 . . . . -179.1(6) ?
O2 C4 O1 C1 . . . . -1.6(9) ?
C5 C4 O1 C1 . . . . 174.5(4) ?
C3 C1 O1 C4 . . . . 179.0(5) ?
C2 C1 O1 C4 . . . . 107.6(6) ?
O3 C27 C28 C46 . . . . -146.1(4) ?
C29 C27 C28 C46 . . . . 107.0(5) ?
O3 C27 C28 C52 . . . . 2.4(7) ?
C29 C27 C28 C52 . . . . -104.5(5) ?
O3 C27 C28 C29 . . . . 106.8(5) ?
O3 C27 C29 C37 . . . . -1.1(8) ?
C28 C27 C29 C37 . . . . 110.4(6) ?
O3 C27 C29 C28 . . . . -111.5(5) ?
C46 C28 C29 C27 . . . . -105.8(5) ?
C52 C28 C29 C27 . . . . 107.1(5) ?
C27 C28 C29 C37 . . . . -117.8(5) ?
C46 C28 C29 C37 . . . . 136.4(5) ?
C52 C28 C29 C37 . . . . -10.7(7) ?
O4 C30 C31 C36 . . . . 18.4(9) ?
O3 C30 C31 C36 . . . . -159.4(5) ?
O4 C30 C31 C32 . . . . -162.9(6) ?
O3 C30 C31 C32 . . . . 19.2(7) ?
C36 C31 C32 C33 . . . . -1.0(8) ?
C30 C31 C32 C33 . . . . -179.6(5) ?
C31 C32 C33 C34 . . . . 0.3(8) ?
C31 C32 C33 Br3 . . . . 178.6(4) ?
C32 C33 C34 C35 . . . . 0.8(9) ?
Br3 C33 C34 C35 . . . . -177.5(5) ?
C33 C34 C35 C36 . . . . -1.3(9) ?
C33 C34 C35 Br4 . . . . 178.2(5) ?
C34 C35 C36 C31 . . . . 0.6(9) ?
Br4 C35 C36 C31 . . . . -178.9(4) ?
C32 C31 C36 C35 . . . . 0.6(8) ?
C30 C31 C36 C35 . . . . 179.2(5) ?
C27 C29 C37 C38 . . . . 26.5(9) ?
C28 C29 C37 C38 . . . . 101.4(6) ?
C27 C29 C37 C44 . . . . -156.1(6) ?
C28 C29 C37 C44 . . . . -81.1(6) ?
C44 C37 C38 C39 . . . . 0.9(8) ?
C29 C37 C38 C39 . . . . 178.3(5) ?
C37 C38 C39 C40 . . . . 177.9(7) ?
C37 C38 C39 C42 . . . . -0.1(8) ?
C38 C39 C40 C41 . . . . -179.9(7) ?
C42 C39 C40 C41 . . . . -1.7(8) ?
C39 C40 C41 N2 . . . . 1.6(9) ?
C38 C39 C42 C43 . . . . -0.7(9) ?
C40 C39 C42 C43 . . . . -179.3(6) ?
C38 C39 C42 N2 . . . . 179.8(5) ?
C40 C39 C42 N2 . . . . 1.2(7) ?
N2 C42 C43 C44 . . . . -180.0(6) ?
C39 C42 C43 C44 . . . . 0.6(9) ?
C42 C43 C44 C37 . . . . 0.2(9) ?
C38 C37 C44 C43 . . . . -1.0(9) ?
C29 C37 C44 C43 . . . . -178.6(6) ?
C27 C28 C46 C51 . . . . 145.1(5) ?
C52 C28 C46 C51 . . . . -2.8(8) ?
C29 C28 C46 C51 . . . . -148.8(5) ?
C27 C28 C46 C47 . . . . -36.5(7) ?
C52 C28 C46 C47 . . . . 175.6(5) ?
C29 C28 C46 C47 . . . . 29.6(7) ?
C51 C46 C47 C48 . . . . 0.3(9) ?
C28 C46 C47 C48 . . . . -178.2(5) ?
C46 C47 C48 C49 . . . . 0.0(10) ?
C47 C48 C49 C50 . . . . -0.6(10) ?
C48 C49 C50 C51 . . . . 0.9(10) ?
C47 C46 C51 C50 . . . . 0.0(9) ?
C28 C46 C51 C50 . . . . 178.5(5) ?
C49 C50 C51 C46 . . . . -0.6(10) ?
C40 C41 N2 C42 . . . . -0.8(8) ?
C40 C41 N2 C45 . . . . -178.2(7) ?
C43 C42 N2 C41 . . . . -179.8(7) ?
C39 C42 N2 C41 . . . . -0.3(7) ?
C43 C42 N2 C45 . . . . -2.3(10) ?
C39 C42 N2 C45 . . . . 177.2(6) ?
O4 C30 O3 C27 . . . . -8.8(8) ?
C31 C30 O3 C27 . . . . 169.0(4) ?
C29 C27 O3 C30 . . . . 172.7(5) ?
C28 C27 O3 C30 . . . . 100.5(5) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C19 H19A O2 2_556 0.96 2.62 3.232(9) 121.8 ?
C36 H36 O2 2_656 0.93 2.70 3.606(7) 164.4 ?
C41 H41 Br2 1_654 0.93 3.45 3.785(7) 103.9 ?
C45 H45B O4 2_745 0.96 2.59 3.207(9) 122.4 ?



_exptl_crystal_recrystallization_method 'Vapour deposition'
