#------------------------------------------------------------------------------
#$Date: 2023-05-05 04:04:00 +0300 (Fri, 05 May 2023) $
#$Revision: 283162 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/82/1568272.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1568272
loop_
_publ_author_name
'Teresa, Javier'
'Velado, Marina'
'Fernández de la Pradilla, Roberto'
'Viso, Alma'
'Lozano, Blanca'
'Tortosa, Mariola'
_publ_section_title
;
 Enantioselective Suzuki cross-coupling of 1,2-diboryl cyclopropanes.
;
_journal_issue                   6
_journal_name_full               'Chemical science'
_journal_page_first              1575
_journal_page_last               1581
_journal_paper_doi               10.1039/d2sc05789a
_journal_volume                  14
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_sum            'C26 H21 Br2 N O2'
_chemical_formula_weight         539.26
_chemical_name_systematic
'(1R,2S,3R)-2-methyl-3-(1-methyl-1H-indol-5-yl)-2-phenylcyclopropyl 3,5-dibromobenzoate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2022-07-18 deposited with the CCDC.	2023-01-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.609(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6562(7)
_cell_length_b                   23.5435(18)
_cell_length_c                   11.2698(9)
_cell_measurement_reflns_used    9045
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      20.7894
_cell_measurement_theta_min      2.9264
_cell_volume                     2276.5(3)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       'Bruker Instrument Service v2010.9.0.0'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1328)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            73125
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.17
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    3.584
_exptl_absorpt_correction_T_max  0.67
_exptl_absorpt_correction_T_min  0.56
_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_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1080
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_size_max          0.256
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.124
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.441
_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)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     563
_refine_ls_number_reflns         8334
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0319
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0272P)²+1.1307P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0627
_refine_ls_wR_factor_ref         0.0698
_reflns_number_gt                6626
_reflns_number_total             8334
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc05789a2.cif
_cod_data_source_block           03534_grande
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 1568272.cif.
;
_cod_database_code               1568272
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
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 . .
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'
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_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_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 ?
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) ?
