#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:15:31 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178427 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/48/4024856.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_4024856
loop_
_publ_author_name
'Katerina Kogan'
'Silvio E. Biali'
_publ_section_title
;
Incorporation of Substituents at the Methylene Linkages of the
Calix[5]arene Skeleton
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7172
_journal_page_last               7175
_journal_paper_doi               10.1021/jo901450x
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C60 H75 Br5 O5'
_chemical_formula_sum            'C60 H75 Br5 O5'
_chemical_formula_weight         1275.75
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.815(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.1109(12)
_cell_length_b                   14.6830(18)
_cell_length_c                   20.472(3)
_cell_measurement_temperature    123(2)
_cell_volume                     2994.8(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_sigmaI/netI    0.0606
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            32631
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    3.399
_exptl_absorpt_correction_T_max  0.6476
_exptl_absorpt_correction_T_min  0.4287
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS V2.05'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1300
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_refine_diff_density_max         1.650
_refine_diff_density_min         -0.828
_refine_diff_density_rms         0.090
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.526(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     682
_refine_ls_number_reflns         13008
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0399
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0489P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0853
_refine_ls_wR_factor_ref         0.0902
_reflns_number_gt                10825
_reflns_number_total             13008
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901450x_si_001.cif
_cod_data_source_block           katya19m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               4024856
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.26374(5) 0.15450(3) -0.06557(2) 0.02965(11) Uani 1 1 d . . .
Br2 Br 0.07692(5) 0.55916(3) 0.02743(2) 0.03097(11) Uani 1 1 d . . .
Br3 Br 0.55211(4) 0.61516(3) 0.36882(2) 0.03183(11) Uani 1 1 d . . .
Br4 Br 0.71024(5) 0.17397(3) 0.51680(2) 0.03814(13) Uani 1 1 d . . .
Br5 Br 0.74171(4) -0.07962(3) 0.22999(2) 0.03060(11) Uani 1 1 d . . .
C1 C 0.4749(4) 0.0957(3) 0.1227(2) 0.0184(8) Uani 1 1 d . . .
C2 C 0.5117(4) 0.0193(3) 0.16116(19) 0.0181(8) Uani 1 1 d . . .
C3 C 0.4434(4) -0.0624(3) 0.1437(2) 0.0206(9) Uani 1 1 d . . .
H3 H 0.4693 -0.1152 0.1696 0.025 Uiso 1 1 calc R . .
C4 C 0.3398(4) -0.0692(3) 0.0903(2) 0.0232(9) Uani 1 1 d . . .
C5 C 0.3055(4) 0.0087(3) 0.0528(2) 0.0219(9) Uani 1 1 d . . .
H5 H 0.2346 0.0057 0.0159 0.026 Uiso 1 1 calc R . .
C6 C 0.3718(4) 0.0909(3) 0.0675(2) 0.0192(9) Uani 1 1 d . . .
C7 C 0.3376(4) 0.1784(3) 0.0299(2) 0.0222(9) Uani 1 1 d . . .
H7 H 0.4234 0.2128 0.0313 0.027 Uiso 1 1 calc R . .
C8 C 0.2580(4) 0.3335(3) 0.0548(2) 0.0205(9) Uani 1 1 d . . .
C9 C 0.2430(4) 0.2397(3) 0.05904(19) 0.0185(8) Uani 1 1 d . . .
C10 C 0.1536(4) 0.2047(3) 0.0961(2) 0.0212(9) Uani 1 1 d . . .
H10 H 0.1440 0.1406 0.0987 0.025 Uiso 1 1 calc R . .
C11 C 0.0761(4) 0.2609(3) 0.1300(2) 0.0242(9) Uani 1 1 d . . .
C12 C 0.0933(4) 0.3546(3) 0.1249(2) 0.0227(9) Uani 1 1 d . . .
H12 H 0.0415 0.3943 0.1472 0.027 Uiso 1 1 calc R . .
C13 C 0.1831(4) 0.3918(3) 0.0885(2) 0.0193(9) Uani 1 1 d . . .
C14 C 0.2115(4) 0.4923(3) 0.0921(2) 0.0229(9) Uani 1 1 d . . .
H14 H 0.3015 0.5021 0.0792 0.028 Uiso 1 1 calc R . .
C15 C 0.3340(4) 0.5088(2) 0.2077(2) 0.0200(9) Uani 1 1 d . . .
C16 C 0.2178(4) 0.5292(3) 0.1617(2) 0.0223(9) Uani 1 1 d . . .
C17 C 0.1135(4) 0.5725(3) 0.1842(2) 0.0241(9) Uani 1 1 d . . .
H17 H 0.0348 0.5864 0.1533 0.029 Uiso 1 1 calc R . .
C18 C 0.1186(4) 0.5968(3) 0.2502(2) 0.0226(9) Uani 1 1 d . . .
C19 C 0.2359(4) 0.5781(3) 0.2944(2) 0.0241(9) Uani 1 1 d . . .
H19 H 0.2433 0.5971 0.3392 0.029 Uiso 1 1 calc R . .
C20 C 0.3425(4) 0.5322(3) 0.2744(2) 0.0229(9) Uani 1 1 d . . .
C21 C 0.4683(4) 0.5053(3) 0.3217(2) 0.0234(9) Uani 1 1 d . . .
H21 H 0.5332 0.4822 0.2938 0.028 Uiso 1 1 calc R . .
C22 C 0.5494(4) 0.3617(3) 0.3799(2) 0.0220(9) Uani 1 1 d . . .
C23 C 0.4539(4) 0.4309(3) 0.3711(2) 0.0223(9) Uani 1 1 d . . .
C24 C 0.3505(4) 0.4273(3) 0.4083(2) 0.0247(9) Uani 1 1 d . . .
H24 H 0.2846 0.4741 0.4023 0.030 Uiso 1 1 calc R . .
C25 C 0.3395(4) 0.3592(3) 0.4533(2) 0.0251(10) Uani 1 1 d . . .
C26 C 0.4380(4) 0.2914(3) 0.4614(2) 0.0236(9) Uani 1 1 d . . .
H26 H 0.4344 0.2447 0.4932 0.028 Uiso 1 1 calc R . .
C27 C 0.5413(4) 0.2904(3) 0.4244(2) 0.0217(9) Uani 1 1 d . . .
C28 C 0.6368(4) 0.2121(3) 0.4252(2) 0.0216(9) Uani 1 1 d . . .
H28 H 0.7141 0.2341 0.4048 0.026 Uiso 1 1 calc R . .
C29 C 0.6342(4) 0.1057(3) 0.3305(2) 0.0202(9) Uani 1 1 d . . .
C30 C 0.5781(4) 0.1317(3) 0.3854(2) 0.0201(9) Uani 1 1 d . . .
C31 C 0.4634(4) 0.0862(3) 0.3972(2) 0.0240(10) Uani 1 1 d . . .
H31 H 0.4255 0.1024 0.4350 0.029 Uiso 1 1 calc R . .
C32 C 0.4035(4) 0.0188(3) 0.3561(2) 0.0241(9) Uani 1 1 d . . .
C33 C 0.4550(4) 0.0003(3) 0.2984(2) 0.0206(9) Uani 1 1 d . . .
H33 H 0.4102 -0.0425 0.2675 0.025 Uiso 1 1 calc R . .
C34 C 0.5695(4) 0.0428(3) 0.2850(2) 0.0196(9) Uani 1 1 d . . .
C35 C 0.6208(4) 0.0283(3) 0.2205(2) 0.0225(9) Uani 1 1 d . . .
H35 H 0.6760 0.0827 0.2132 0.027 Uiso 1 1 calc R . .
C36 C 0.4985(5) 0.2343(3) 0.1862(2) 0.0337(11) Uani 1 1 d . . .
H36A H 0.4634 0.2917 0.1657 0.051 Uiso 1 1 calc R . .
H36B H 0.5745 0.2471 0.2216 0.051 Uiso 1 1 calc R . .
H36C H 0.4277 0.2032 0.2050 0.051 Uiso 1 1 calc R . .
C37 C 0.2670(5) -0.1596(3) 0.0720(2) 0.0313(11) Uani 1 1 d . . .
C38 C 0.215(2) -0.1941(14) 0.1401(11) 0.063(6) Uani 0.30 1 d P . .
H38A H 0.2917 -0.2174 0.1716 0.095 Uiso 0.30 1 calc PR . .
H38B H 0.1485 -0.2426 0.1290 0.095 Uiso 0.30 1 calc PR . .
H38C H 0.1745 -0.1429 0.1601 0.095 Uiso 0.30 1 calc PR . .
C39 C 0.143(2) -0.1534(12) 0.0246(13) 0.054(6) Uani 0.30 1 d P . .
H39A H 0.0789 -0.1146 0.0428 0.081 Uiso 0.30 1 calc PR . .
H39B H 0.1043 -0.2144 0.0161 0.081 Uiso 0.30 1 calc PR . .
H39C H 0.1610 -0.1271 -0.0169 0.081 Uiso 0.30 1 calc PR . .
C40 C 0.3686(17) -0.2291(12) 0.0567(10) 0.038(4) Uani 0.30 1 d P . .
H40A H 0.4030 -0.2106 0.0168 0.057 Uiso 0.30 1 calc PR . .
H40B H 0.3253 -0.2888 0.0494 0.057 Uiso 0.30 1 calc PR . .
H40C H 0.4431 -0.2329 0.0941 0.057 Uiso 0.30 1 calc PR . .
C38A C 0.3353(10) -0.2398(5) 0.1075(5) 0.061(3) Uani 0.70 1 d P . .
H38D H 0.4309 -0.2387 0.1042 0.092 Uiso 0.70 1 calc PR . .
H38E H 0.2946 -0.2959 0.0874 0.092 Uiso 0.70 1 calc PR . .
H38F H 0.3253 -0.2375 0.1543 0.092 Uiso 0.70 1 calc PR . .
C39A C 0.1217(8) -0.1507(5) 0.0810(6) 0.053(2) Uani 0.70 1 d P . .
H39D H 0.1181 -0.1377 0.1277 0.080 Uiso 0.70 1 calc PR . .
H39E H 0.0742 -0.2078 0.0681 0.080 Uiso 0.70 1 calc PR . .
H39F H 0.0789 -0.1009 0.0533 0.080 Uiso 0.70 1 calc PR . .
C40A C 0.2696(10) -0.1786(5) -0.0042(4) 0.054(2) Uani 0.70 1 d P . .
H40D H 0.2279 -0.1275 -0.0308 0.081 Uiso 0.70 1 calc PR . .
H40E H 0.2198 -0.2346 -0.0178 0.081 Uiso 0.70 1 calc PR . .
H40F H 0.3628 -0.1855 -0.0109 0.081 Uiso 0.70 1 calc PR . .
C41 C 0.3059(6) 0.4037(4) -0.0441(3) 0.0441(13) Uani 1 1 d . . .
H41A H 0.2828 0.3528 -0.0748 0.066 Uiso 1 1 calc R . .
H41B H 0.3758 0.4409 -0.0588 0.066 Uiso 1 1 calc R . .
H41C H 0.2260 0.4412 -0.0432 0.066 Uiso 1 1 calc R . .
C42 C -0.0021(6) 0.2251(4) 0.1825(3) 0.0400(13) Uani 1 1 d . . .
C43 C -0.0326(5) 0.1240(3) 0.1738(3) 0.0434(13) Uani 1 1 d . . .
H43A H -0.0823 0.1035 0.2082 0.065 Uiso 1 1 calc R . .
H43B H 0.0517 0.0899 0.1775 0.065 Uiso 1 1 calc R . .
H43C H -0.0868 0.1134 0.1300 0.065 Uiso 1 1 calc R . .
C44 C 0.0851(8) 0.2400(5) 0.2509(3) 0.080(3) Uani 1 1 d . . .
H44A H 0.1031 0.3052 0.2578 0.120 Uiso 1 1 calc R . .
H44B H 0.1701 0.2072 0.2531 0.120 Uiso 1 1 calc R . .
H44C H 0.0376 0.2172 0.2855 0.120 Uiso 1 1 calc R . .
C45 C -0.1341(6) 0.2755(4) 0.1808(4) 0.065(2) Uani 1 1 d . . .
H45A H -0.1177 0.3413 0.1816 0.097 Uiso 1 1 calc R . .
H45B H -0.1737 0.2582 0.2195 0.097 Uiso 1 1 calc R . .
H45C H -0.1960 0.2594 0.1402 0.097 Uiso 1 1 calc R . .
C46 C 0.5322(5) 0.5162(4) 0.1618(3) 0.0383(12) Uani 1 1 d . . .
H46A H 0.4883 0.5501 0.1228 0.057 Uiso 1 1 calc R . .
H46B H 0.6028 0.4773 0.1494 0.057 Uiso 1 1 calc R . .
H46C H 0.5720 0.5591 0.1963 0.057 Uiso 1 1 calc R . .
C47 C -0.0044(4) 0.6416(3) 0.2719(2) 0.0287(10) Uani 1 1 d . . .
C48 C -0.1277(5) 0.5815(4) 0.2497(2) 0.0416(13) Uani 1 1 d . . .
H48A H -0.1141 0.5221 0.2717 0.062 Uiso 1 1 calc R . .
H48B H -0.1405 0.5730 0.2016 0.062 Uiso 1 1 calc R . .
H48C H -0.2072 0.6108 0.2617 0.062 Uiso 1 1 calc R . .
C49 C -0.0301(6) 0.7341(4) 0.2366(3) 0.0529(16) Uani 1 1 d . . .
H49A H -0.1142 0.7601 0.2460 0.079 Uiso 1 1 calc R . .
H49B H -0.0367 0.7255 0.1886 0.079 Uiso 1 1 calc R . .
H49C H 0.0442 0.7757 0.2526 0.079 Uiso 1 1 calc R . .
C50 C 0.0111(5) 0.6562(4) 0.3451(2) 0.0468(14) Uani 1 1 d . . .
H50A H 0.0893 0.6950 0.3599 0.070 Uiso 1 1 calc R . .
H50B H 0.0238 0.5973 0.3679 0.070 Uiso 1 1 calc R . .
H50C H -0.0697 0.6857 0.3556 0.070 Uiso 1 1 calc R . .
C51 C 0.7751(5) 0.3981(3) 0.3744(3) 0.0384(12) Uani 1 1 d . . .
H51A H 0.7649 0.4640 0.3793 0.058 Uiso 1 1 calc R . .
H51B H 0.8453 0.3861 0.3479 0.058 Uiso 1 1 calc R . .
H51C H 0.8001 0.3702 0.4182 0.058 Uiso 1 1 calc R . .
C52 C 0.2239(4) 0.3554(3) 0.4944(2) 0.0285(10) Uani 1 1 d . . .
C53 C 0.1200(5) 0.4279(4) 0.4737(3) 0.0414(12) Uani 1 1 d . . .
H53A H 0.0463 0.4208 0.4988 0.062 Uiso 1 1 calc R . .
H53B H 0.0851 0.4220 0.4262 0.062 Uiso 1 1 calc R . .
H53C H 0.1609 0.4881 0.4826 0.062 Uiso 1 1 calc R . .
C54 C 0.2808(5) 0.3659(4) 0.5670(2) 0.0394(12) Uani 1 1 d . . .
H54A H 0.3247 0.4255 0.5746 0.059 Uiso 1 1 calc R . .
H54B H 0.3467 0.3177 0.5807 0.059 Uiso 1 1 calc R . .
H54C H 0.2082 0.3616 0.5930 0.059 Uiso 1 1 calc R . .
C55 C 0.1536(5) 0.2623(3) 0.4826(3) 0.0429(13) Uani 1 1 d . . .
H55A H 0.0778 0.2598 0.5067 0.064 Uiso 1 1 calc R . .
H55B H 0.2175 0.2137 0.4986 0.064 Uiso 1 1 calc R . .
H55C H 0.1208 0.2541 0.4351 0.064 Uiso 1 1 calc R . .
C56 C 0.8676(4) 0.1011(4) 0.3598(2) 0.0311(11) Uani 1 1 d . . .
H56A H 0.8555 0.1010 0.4063 0.047 Uiso 1 1 calc R . .
H56B H 0.9493 0.1349 0.3556 0.047 Uiso 1 1 calc R . .
H56C H 0.8755 0.0383 0.3448 0.047 Uiso 1 1 calc R . .
C57 C 0.2805(5) -0.0355(3) 0.3691(3) 0.0350(12) Uani 1 1 d . . .
C58 C 0.2378(9) -0.0091(7) 0.4334(3) 0.108(4) Uani 1 1 d . . .
H58A H 0.2103 0.0550 0.4314 0.162 Uiso 1 1 calc R . .
H58B H 0.3130 -0.0177 0.4700 0.162 Uiso 1 1 calc R . .
H58C H 0.1622 -0.0473 0.4407 0.162 Uiso 1 1 calc R . .
C59 C 0.1639(5) -0.0233(4) 0.3135(3) 0.0479(14) Uani 1 1 d . . .
H59A H 0.0869 -0.0582 0.3231 0.072 Uiso 1 1 calc R . .
H59B H 0.1888 -0.0449 0.2720 0.072 Uiso 1 1 calc R . .
H59C H 0.1400 0.0414 0.3092 0.072 Uiso 1 1 calc R . .
C60 C 0.3148(6) -0.1375(4) 0.3699(4) 0.070(2) Uani 1 1 d . . .
H60A H 0.3897 -0.1499 0.4059 0.104 Uiso 1 1 calc R . .
H60B H 0.3402 -0.1546 0.3275 0.104 Uiso 1 1 calc R . .
H60C H 0.2363 -0.1730 0.3769 0.104 Uiso 1 1 calc R . .
O1 O 0.5427(3) 0.17632(19) 0.13634(14) 0.0275(7) Uani 1 1 d . . .
O2 O 0.3553(3) 0.3686(2) 0.02235(15) 0.0284(7) Uani 1 1 d . . .
O3 O 0.4344(3) 0.46028(19) 0.18667(15) 0.0258(7) Uani 1 1 d . . .
O4 O 0.6504(3) 0.3600(2) 0.34163(15) 0.0287(7) Uani 1 1 d . . .
O5 O 0.7547(3) 0.14356(19) 0.32014(13) 0.0214(6) Uani 1 1 d . . .
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'
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'
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
O1 C1 C2 120.5(3) . . ?
O1 C1 C6 118.9(4) . . ?
C2 C1 C6 120.6(4) . . ?
C1 C2 C3 118.4(4) . . ?
C1 C2 C35 118.5(4) . . ?
C3 C2 C35 123.0(4) . . ?
C4 C3 C2 122.6(4) . . ?
C4 C3 H3 118.7 . . ?
C2 C3 H3 118.7 . . ?
C3 C4 C5 117.5(4) . . ?
C3 C4 C37 121.6(4) . . ?
C5 C4 C37 120.9(4) . . ?
C6 C5 C4 122.1(4) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C5 C6 C1 118.9(4) . . ?
C5 C6 C7 124.8(4) . . ?
C1 C6 C7 116.3(4) . . ?
C9 C7 C6 114.4(3) . . ?
C9 C7 Br1 109.6(3) . . ?
C6 C7 Br1 111.3(3) . . ?
C9 C7 H7 107.1 . . ?
C6 C7 H7 107.1 . . ?
Br1 C7 H7 107.1 . . ?
O2 C8 C9 119.6(4) . . ?
O2 C8 C13 120.0(4) . . ?
C9 C8 C13 120.1(4) . . ?
C10 C9 C8 119.5(4) . . ?
C10 C9 C7 121.1(4) . . ?
C8 C9 C7 118.9(4) . . ?
C9 C10 C11 122.0(4) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
C12 C11 C10 117.2(4) . . ?
C12 C11 C42 118.6(4) . . ?
C10 C11 C42 123.0(4) . . ?
C13 C12 C11 122.2(4) . . ?
C13 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
C12 C13 C8 119.0(4) . . ?
C12 C13 C14 119.9(4) . . ?
C8 C13 C14 120.6(4) . . ?
C13 C14 C16 112.0(3) . . ?
C13 C14 Br2 110.4(3) . . ?
C16 C14 Br2 111.4(3) . . ?
C13 C14 H14 107.6 . . ?
C16 C14 H14 107.6 . . ?
Br2 C14 H14 107.6 . . ?
O3 C15 C20 120.7(4) . . ?
O3 C15 C16 118.6(4) . . ?
C20 C15 C16 120.5(4) . . ?
C17 C16 C15 118.4(4) . . ?
C17 C16 C14 124.5(4) . . ?
C15 C16 C14 116.7(4) . . ?
C16 C17 C18 122.6(4) . . ?
C16 C17 H17 118.7 . . ?
C18 C17 H17 118.7 . . ?
C19 C18 C17 117.9(4) . . ?
C19 C18 C47 122.6(4) . . ?
C17 C18 C47 119.5(4) . . ?
C18 C19 C20 121.5(4) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 H19 119.2 . . ?
C19 C20 C15 119.0(4) . . ?
C19 C20 C21 123.2(4) . . ?
C15 C20 C21 117.8(4) . . ?
C23 C21 C20 116.8(3) . . ?
C23 C21 Br3 110.0(3) . . ?
C20 C21 Br3 109.9(3) . . ?
C23 C21 H21 106.5 . . ?
C20 C21 H21 106.5 . . ?
Br3 C21 H21 106.5 . . ?
O4 C22 C23 120.0(4) . . ?
O4 C22 C27 118.9(4) . . ?
C23 C22 C27 121.0(4) . . ?
C22 C23 C24 118.0(4) . . ?
C22 C23 C21 118.0(4) . . ?
C24 C23 C21 123.9(4) . . ?
C25 C24 C23 123.0(4) . . ?
C25 C24 H24 118.5 . . ?
C23 C24 H24 118.5 . . ?
C24 C25 C26 117.4(4) . . ?
C24 C25 C52 122.9(4) . . ?
C26 C25 C52 119.7(4) . . ?
C27 C26 C25 121.8(4) . . ?
C27 C26 H26 119.1 . . ?
C25 C26 H26 119.1 . . ?
C26 C27 C22 118.7(4) . . ?
C26 C27 C28 122.9(4) . . ?
C22 C27 C28 118.2(4) . . ?
C30 C28 C27 113.8(3) . . ?
C30 C28 Br4 110.1(3) . . ?
C27 C28 Br4 111.4(3) . . ?
C30 C28 H28 107.1 . . ?
C27 C28 H28 107.1 . . ?
Br4 C28 H28 107.1 . . ?
O5 C29 C34 119.1(3) . . ?
O5 C29 C30 120.1(4) . . ?
C34 C29 C30 120.8(4) . . ?
C31 C30 C29 118.2(4) . . ?
C31 C30 C28 123.2(4) . . ?
C29 C30 C28 118.4(4) . . ?
C32 C31 C30 122.2(4) . . ?
C32 C31 H31 118.9 . . ?
C30 C31 H31 118.9 . . ?
C31 C32 C33 118.0(4) . . ?
C31 C32 C57 123.6(4) . . ?
C33 C32 C57 118.3(4) . . ?
C34 C33 C32 121.7(4) . . ?
C34 C33 H33 119.2 . . ?
C32 C33 H33 119.2 . . ?
C33 C34 C29 118.6(4) . . ?
C33 C34 C35 122.2(4) . . ?
C29 C34 C35 119.0(4) . . ?
C2 C35 C34 113.9(3) . . ?
C2 C35 Br5 111.2(3) . . ?
C34 C35 Br5 108.9(3) . . ?
C2 C35 H35 107.5 . . ?
C34 C35 H35 107.5 . . ?
Br5 C35 H35 107.5 . . ?
O1 C36 H36A 109.5 . . ?
O1 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
O1 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C39 C37 C38A 130.6(8) . . ?
C39 C37 C40 116.3(12) . . ?
C38A C37 C40 45.2(8) . . ?
C39 C37 C39A 48.0(10) . . ?
C38A C37 C39A 112.7(6) . . ?
C40 C37 C39A 141.8(8) . . ?
C39 C37 C4 115.7(8) . . ?
C38A C37 C4 113.7(4) . . ?
C40 C37 C4 108.6(7) . . ?
C39A C37 C4 109.3(4) . . ?
C39 C37 C40A 60.9(11) . . ?
C38A C37 C40A 104.8(6) . . ?
C40 C37 C40A 63.5(9) . . ?
C39A C37 C40A 108.3(6) . . ?
C4 C37 C40A 107.8(4) . . ?
C39 C37 C38 102.7(13) . . ?
C38A C37 C38 62.1(10) . . ?
C40 C37 C38 106.9(12) . . ?
C39A C37 C38 58.0(9) . . ?
C4 C37 C38 105.5(8) . . ?
C40A C37 C38 146.7(8) . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C37 C39 H39A 109.5 . . ?
C37 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C37 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C37 C40 H40A 109.5 . . ?
C37 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C37 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C37 C38A H38D 109.5 . . ?
C37 C38A H38E 109.5 . . ?
H38D C38A H38E 109.5 . . ?
C37 C38A H38F 109.5 . . ?
H38D C38A H38F 109.5 . . ?
H38E C38A H38F 109.5 . . ?
C37 C39A H39D 109.5 . . ?
C37 C39A H39E 109.5 . . ?
H39D C39A H39E 109.5 . . ?
C37 C39A H39F 109.5 . . ?
H39D C39A H39F 109.5 . . ?
H39E C39A H39F 109.5 . . ?
C37 C40A H40D 109.5 . . ?
C37 C40A H40E 109.5 . . ?
H40D C40A H40E 109.5 . . ?
C37 C40A H40F 109.5 . . ?
H40D C40A H40F 109.5 . . ?
H40E C40A H40F 109.5 . . ?
O2 C41 H41A 109.5 . . ?
O2 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
O2 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C43 C42 C45 108.2(5) . . ?
C43 C42 C11 111.8(4) . . ?
C45 C42 C11 111.9(4) . . ?
C43 C42 C44 108.6(5) . . ?
C45 C42 C44 108.4(5) . . ?
C11 C42 C44 107.8(4) . . ?
C42 C43 H43A 109.5 . . ?
C42 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C42 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C42 C44 H44A 109.5 . . ?
C42 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C42 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C42 C45 H45A 109.5 . . ?
C42 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
C42 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
O3 C46 H46A 109.5 . . ?
O3 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
O3 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C50 C47 C48 108.7(4) . . ?
C50 C47 C18 113.5(4) . . ?
C48 C47 C18 109.0(4) . . ?
C50 C47 C49 108.9(4) . . ?
C48 C47 C49 107.8(4) . . ?
C18 C47 C49 108.8(4) . . ?
C47 C48 H48A 109.5 . . ?
C47 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C47 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C47 C49 H49A 109.5 . . ?
C47 C49 H49B 109.5 . . ?
H49A C49 H49B 109.5 . . ?
C47 C49 H49C 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C47 C50 H50A 109.5 . . ?
C47 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
C47 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
O4 C51 H51A 109.5 . . ?
O4 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
O4 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C53 C52 C54 109.6(4) . . ?
C53 C52 C55 107.6(4) . . ?
C54 C52 C55 109.5(4) . . ?
C53 C52 C25 112.0(4) . . ?
C54 C52 C25 109.5(4) . . ?
C55 C52 C25 108.5(4) . . ?
C52 C53 H53A 109.5 . . ?
C52 C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
C52 C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C52 C54 H54A 109.5 . . ?
C52 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
C52 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
C52 C55 H55A 109.5 . . ?
C52 C55 H55B 109.5 . . ?
H55A C55 H55B 109.5 . . ?
C52 C55 H55C 109.5 . . ?
H55A C55 H55C 109.5 . . ?
H55B C55 H55C 109.5 . . ?
O5 C56 H56A 109.5 . . ?
O5 C56 H56B 109.5 . . ?
H56A C56 H56B 109.5 . . ?
O5 C56 H56C 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 109.5 . . ?
C59 C57 C58 109.0(5) . . ?
C59 C57 C60 105.8(5) . . ?
C58 C57 C60 109.9(6) . . ?
C59 C57 C32 111.1(4) . . ?
C58 C57 C32 112.2(5) . . ?
C60 C57 C32 108.7(4) . . ?
C57 C58 H58A 109.5 . . ?
C57 C58 H58B 109.5 . . ?
H58A C58 H58B 109.5 . . ?
C57 C58 H58C 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
C57 C59 H59A 109.5 . . ?
C57 C59 H59B 109.5 . . ?
H59A C59 H59B 109.5 . . ?
C57 C59 H59C 109.5 . . ?
H59A C59 H59C 109.5 . . ?
H59B C59 H59C 109.5 . . ?
C57 C60 H60A 109.5 . . ?
C57 C60 H60B 109.5 . . ?
H60A C60 H60B 109.5 . . ?
C57 C60 H60C 109.5 . . ?
H60A C60 H60C 109.5 . . ?
H60B C60 H60C 109.5 . . ?
C1 O1 C36 116.3(3) . . ?
C8 O2 C41 115.0(3) . . ?
C15 O3 C46 113.9(3) . . ?
C22 O4 C51 113.6(3) . . ?
C29 O5 C56 112.1(3) . . ?
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 C7 2.002(4) . ?
Br2 C14 1.989(4) . ?
Br3 C21 1.993(4) . ?
Br4 C28 1.976(4) . ?
Br5 C35 1.991(4) . ?
C1 O1 1.373(5) . ?
C1 C2 1.384(6) . ?
C1 C6 1.403(6) . ?
C2 C3 1.399(6) . ?
C2 C35 1.501(6) . ?
C3 C4 1.383(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(6) . ?
C4 C37 1.532(6) . ?
C5 C6 1.388(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.507(6) . ?
C7 C9 1.507(6) . ?
C7 H7 1.0000 . ?
C8 O2 1.377(5) . ?
C8 C9 1.390(6) . ?
C8 C13 1.399(6) . ?
C9 C10 1.375(6) . ?
C10 C11 1.401(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.393(6) . ?
C11 C42 1.532(6) . ?
C12 C13 1.382(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.503(6) . ?
C14 C16 1.516(6) . ?
C14 H14 1.0000 . ?
C15 O3 1.369(5) . ?
C15 C20 1.395(6) . ?
C15 C16 1.406(6) . ?
C16 C17 1.376(6) . ?
C17 C18 1.391(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.390(6) . ?
C18 C47 1.537(6) . ?
C19 C20 1.391(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.513(6) . ?
C21 C23 1.513(6) . ?
C21 H21 1.0000 . ?
C22 O4 1.390(5) . ?
C22 C23 1.392(6) . ?
C22 C27 1.397(6) . ?
C23 C24 1.394(6) . ?
C24 C25 1.377(6) . ?
C24 H24 0.9500 . ?
C25 C26 1.398(6) . ?
C25 C52 1.554(6) . ?
C26 C27 1.392(6) . ?
C26 H26 0.9500 . ?
C27 C28 1.500(6) . ?
C28 C30 1.498(6) . ?
C28 H28 1.0000 . ?
C29 O5 1.388(5) . ?
C29 C34 1.394(6) . ?
C29 C30 1.396(6) . ?
C30 C31 1.395(6) . ?
C31 C32 1.371(6) . ?
C31 H31 0.9500 . ?
C32 C33 1.397(6) . ?
C32 C57 1.539(6) . ?
C33 C34 1.383(6) . ?
C33 H33 0.9500 . ?
C34 C35 1.513(6) . ?
C35 H35 1.0000 . ?
C36 O1 1.458(5) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 C39 1.454(18) . ?
C37 C38A 1.491(9) . ?
C37 C40 1.518(18) . ?
C37 C39A 1.518(9) . ?
C37 C40A 1.588(9) . ?
C37 C38 1.65(2) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C38A H38D 0.9800 . ?
C38A H38E 0.9800 . ?
C38A H38F 0.9800 . ?
C39A H39D 0.9800 . ?
C39A H39E 0.9800 . ?
C39A H39F 0.9800 . ?
C40A H40D 0.9800 . ?
C40A H40E 0.9800 . ?
C40A H40F 0.9800 . ?
C41 O2 1.461(6) . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 C43 1.521(7) . ?
C42 C45 1.521(8) . ?
C42 C44 1.537(8) . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?
C46 O3 1.444(5) . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C47 C50 1.496(6) . ?
C47 C48 1.532(6) . ?
C47 C49 1.541(7) . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?
C50 H50A 0.9800 . ?
C50 H50B 0.9800 . ?
C50 H50C 0.9800 . ?
C51 O4 1.437(6) . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C52 C53 1.505(7) . ?
C52 C54 1.508(7) . ?
C52 C55 1.540(7) . ?
C53 H53A 0.9800 . ?
C53 H53B 0.9800 . ?
C53 H53C 0.9800 . ?
C54 H54A 0.9800 . ?
C54 H54B 0.9800 . ?
C54 H54C 0.9800 . ?
C55 H55A 0.9800 . ?
C55 H55B 0.9800 . ?
C55 H55C 0.9800 . ?
C56 O5 1.427(5) . ?
C56 H56A 0.9800 . ?
C56 H56B 0.9800 . ?
C56 H56C 0.9800 . ?
C57 C59 1.504(7) . ?
C57 C58 1.505(8) . ?
C57 C60 1.536(8) . ?
C58 H58A 0.9800 . ?
C58 H58B 0.9800 . ?
C58 H58C 0.9800 . ?
C59 H59A 0.9800 . ?
C59 H59B 0.9800 . ?
C59 H59C 0.9800 . ?
C60 H60A 0.9800 . ?
C60 H60B 0.9800 . ?
C60 H60C 0.9800 . ?
