#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/74/1517402.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_1517402
loop_
_publ_author_name
'Mariaule, Gaëlle'
'Newsome, Gregory'
'Toullec, Patrick Y.'
'Belmont, Philippe'
'Michelet, Véronique'
_publ_section_title
;
 Silver-Catalyzed Domino Hydroarylation/Cycloisomerization Reactions of
 ortho-Alkynylbenzaldehydes: An Entry to Functionalized Isochromene
 Derivatives.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4570
_journal_paper_doi               10.1021/ol5021256
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C24 H21 Br O4,0.25 (C H2 Cl2)'
_chemical_formula_sum            'C24.25 H21.5 Br Cl0.5 O4'
_chemical_formula_weight         474.55
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                115.0760(10)
_cell_angle_beta                 103.3320(10)
_cell_angle_gamma                92.5870(10)
_cell_formula_units_Z            4
_cell_length_a                   11.2333(3)
_cell_length_b                   13.7701(3)
_cell_length_c                   15.8106(4)
_cell_measurement_reflns_used    9783
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      68.23
_cell_measurement_theta_min      3.21
_cell_volume                     2126.93(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multi layer miror'
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            33923
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.381
_diffrn_reflns_theta_min         3.211
_exptl_absorpt_coefficient_mu    3.447
_exptl_absorpt_correction_T_max  0.585
_exptl_absorpt_correction_T_min  0.488
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS, Bruker AXS Inc., Madison, 
Wisconsin, USA. 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blcok
_exptl_crystal_F_000             970
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.525
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.00035(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.221
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     593
_refine_ls_number_reflns         7699
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.221
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0509
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0047P)²+4.0085P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1050
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7483
_reflns_number_total             7699
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol5021256_si_001.cif
_cod_data_source_block           gm521_0m
_cod_depositor_comments          'Adding full bibliography for 1517402.cif.'
_cod_original_cell_volume        2126.92(9)
_cod_original_formula_sum        'C24.25 H21.50 Br Cl0.50 O4'
_cod_database_code               1517402
#BEGIN Tags that were not found in dictionaries:
_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.
;
_shelxl_version_number           2013-4
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_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
Br24 Br 0.12780(4) 0.51242(4) 1.11408(3) 0.06366(15) Uani 1 1 d . . . . .
O20 O 0.2919(2) 0.03986(17) 0.83082(16) 0.0391(5) Uani 1 1 d . . . . .
O21 O 0.4994(2) -0.06324(19) 0.86376(17) 0.0420(5) Uani 1 1 d . . . . .
O22 O 0.0866(3) -0.2351(2) 0.7157(2) 0.0678(9) Uani 1 1 d . . . . .
O23 O 0.3590(2) -0.39260(18) 0.87752(18) 0.0438(6) Uani 1 1 d . . . . .
C1 C 0.2626(3) -0.0690(3) 0.7514(2) 0.0365(7) Uani 1 1 d . . . . .
H1 H 0.1707 -0.0845 0.7226 0.044 Uiso 1 1 calc R U . . .
C2 C 0.2647(3) 0.1191(2) 0.8014(2) 0.0340(7) Uani 1 1 d . . . . .
C3 C 0.2686(3) 0.1071(3) 0.7139(2) 0.0368(7) Uani 1 1 d . . . . .
H3 H 0.2426 0.1603 0.6935 0.044 Uiso 1 1 calc R U . . .
C4 C 0.3123(3) 0.0132(2) 0.6491(2) 0.0338(7) Uani 1 1 d . . . . .
C5 C 0.3477(3) 0.0071(3) 0.5681(2) 0.0407(8) Uani 1 1 d . . . . .
H5 H 0.3427 0.0661 0.5519 0.049 Uiso 1 1 calc R U . . .
C6 C 0.3898(3) -0.0843(3) 0.5115(3) 0.0444(8) Uani 1 1 d . . . . .
H6 H 0.4113 -0.0889 0.4554 0.053 Uiso 1 1 calc R U . . .
C7 C 0.4011(3) -0.1694(3) 0.5359(3) 0.0450(8) Uani 1 1 d . . . . .
H7 H 0.4321 -0.2314 0.4976 0.054 Uiso 1 1 calc R U . . .
C8 C 0.3670(3) -0.1640(3) 0.6165(2) 0.0403(8) Uani 1 1 d . . . . .
H8 H 0.3755 -0.2221 0.6336 0.048 Uiso 1 1 calc R U . . .
C9 C 0.3205(3) -0.0742(2) 0.6723(2) 0.0339(7) Uani 1 1 d . . . . .
C10 C 0.2947(3) -0.1500(3) 0.7904(2) 0.0353(7) Uani 1 1 d . . . . .
C11 C 0.4122(3) -0.1478(2) 0.8441(2) 0.0333(7) Uani 1 1 d . . . . .
C11' C 0.2016(3) -0.2355(3) 0.7685(2) 0.0414(8) Uani 1 1 d . . . . .
C12 C 0.4398(3) -0.2272(3) 0.8755(2) 0.0341(7) Uani 1 1 d . . . . .
H12 H 0.5209 -0.2243 0.9123 0.041 Uiso 1 1 calc R U . . .
C12' C 0.2266(3) -0.3147(3) 0.7989(2) 0.0409(8) Uani 1 1 d . . . . .
H12' H 0.1627 -0.3718 0.7841 0.049 Uiso 1 1 calc R U . . .
C13 C 0.3454(3) -0.3098(2) 0.8511(2) 0.0337(7) Uani 1 1 d . . . . .
C14 C 0.6165(3) -0.0471(3) 0.9308(3) 0.0458(8) Uani 1 1 d . . . . .
H14A H 0.6034 -0.0485 0.9895 0.069 Uiso 1 1 calc R U . . .
H14B H 0.6637 0.0234 0.9481 0.069 Uiso 1 1 calc R U . . .
H14C H 0.6626 -0.1051 0.9009 0.069 Uiso 1 1 calc R U . . .
C14' C -0.0092(5) -0.3215(5) 0.6913(5) 0.120(3) Uani 1 1 d . . . . .
H14D H 0.0117 -0.3906 0.6490 0.180 Uiso 1 1 calc R U . . .
H14E H -0.0876 -0.3096 0.6574 0.180 Uiso 1 1 calc R U . . .
H14F H -0.0177 -0.3238 0.7508 0.180 Uiso 1 1 calc R U . . .
C15 C 0.4782(4) -0.3928(3) 0.9327(3) 0.0571(10) Uani 1 1 d . . . . .
H15A H 0.5392 -0.3929 0.8973 0.086 Uiso 1 1 calc R U . . .
H15B H 0.4766 -0.4579 0.9435 0.086 Uiso 1 1 calc R U . . .
H15C H 0.5010 -0.3278 0.9955 0.086 Uiso 1 1 calc R U . . .
C16 C 0.2358(3) 0.2150(3) 0.8776(2) 0.0355(7) Uani 1 1 d . . . . .
C17 C 0.2060(3) 0.2078(3) 0.9554(2) 0.0429(8) Uani 1 1 d . . . . .
H17 H 0.2066 0.1413 0.9601 0.051 Uiso 1 1 calc R U . . .
C17' C 0.2359(3) 0.3142(3) 0.8733(3) 0.0454(8) Uani 1 1 d . . . . .
H17' H 0.2579 0.3210 0.8213 0.054 Uiso 1 1 calc R U . . .
C18 C 0.1753(3) 0.2966(3) 1.0267(3) 0.0478(9) Uani 1 1 d . . . . .
H18 H 0.1555 0.2913 1.0800 0.057 Uiso 1 1 calc R U . . .
C18' C 0.2045(4) 0.4026(3) 0.9432(3) 0.0496(9) Uani 1 1 d . . . . .
H18' H 0.2039 0.4696 0.9393 0.060 Uiso 1 1 calc R U . . .
C19 C 0.1741(3) 0.3921(3) 1.0185(3) 0.0450(8) Uani 1 1 d . . . . .
Br48 Br 0.25062(5) -0.24872(4) 0.05519(3) 0.06325(15) Uani 1 1 d . . . . .
O45 O 0.4471(3) 0.2866(2) 0.6694(2) 0.0728(9) Uani 1 1 d . . . . .
O46 O 0.2444(3) 0.4614(2) 0.4965(3) 0.0910(13) Uani 1 1 d . . . . .
O47 O 0.6508(2) 0.6236(2) 0.7212(2) 0.0516(6) Uani 1 1 d . . . . .
O44 O 0.2650(7) 0.1840(6) 0.4726(6) 0.0322(15) Uani 0.5 1 d . . P A 1
C25 C 0.2267(7) 0.2930(5) 0.5170(5) 0.0272(16) Uani 0.5 1 d . . P A 1
H25 H 0.1778 0.3067 0.4629 0.033 Uiso 0.5 1 calc R U P A 1
C34 C 0.342(2) 0.3776(17) 0.5685(11) 0.031(3) Uani 0.5 1 d . . P A 1
C39 C 0.2165(15) 0.5513(14) 0.5009(10) 0.072(4) Uani 0.5 1 d . . P B 1
H39A H 0.2187 0.6006 0.5679 0.108 Uiso 0.5 1 calc R U P B 1
H39B H 0.1331 0.5391 0.4582 0.108 Uiso 0.5 1 calc R U P B 1
H39C H 0.2763 0.5837 0.4799 0.108 Uiso 0.5 1 calc R U P B 1
O44A O 0.2346(7) 0.2115(6) 0.4552(6) 0.0368(15) Uani 0.5 1 d . . P A 2
C25A C 0.2520(7) 0.2762(6) 0.5544(7) 0.0401(17) Uani 0.5 1 d . . P A 2
H25A H 0.2870 0.2286 0.5840 0.048 Uiso 0.5 1 calc R U P A 2
C34A C 0.3570(18) 0.3712(15) 0.5956(10) 0.028(3) Uani 0.5 1 d . . P A 2
C39A C 0.2405(14) 0.5597(11) 0.4678(10) 0.057(3) Uani 0.5 1 d . . P B 2
H39D H 0.2381 0.6267 0.5241 0.086 Uiso 0.5 1 calc R U P B 2
H39E H 0.1662 0.5438 0.4143 0.086 Uiso 0.5 1 calc R U P B 2
H39F H 0.3145 0.5689 0.4475 0.086 Uiso 0.5 1 calc R U P B 2
C26 C 0.1554(3) 0.1104(3) 0.4172(2) 0.0391(8) Uani 1 1 d . . . . .
C27 C 0.0566(3) 0.1116(3) 0.4503(2) 0.0381(7) Uani 1 1 d . . . . .
H27 H -0.0079 0.0505 0.4169 0.046 Uiso 1 1 calc R U . . .
C28 C 0.0448(3) 0.2037(3) 0.5359(2) 0.0378(7) Uani 1 1 d . . . . .
C29 C -0.0550(4) 0.2067(4) 0.5739(3) 0.0684(13) Uani 1 1 d . . . . .
H29 H -0.1205 0.1466 0.5435 0.082 Uiso 1 1 calc R U . . .
C30 C -0.0593(5) 0.2974(4) 0.6561(4) 0.099(2) Uani 1 1 d . . . . .
H30 H -0.1281 0.2995 0.6820 0.119 Uiso 1 1 calc R U . . .
C31 C 0.0360(5) 0.3852(4) 0.7011(3) 0.0790(16) Uani 1 1 d . . . . .
H31 H 0.0329 0.4470 0.7579 0.095 Uiso 1 1 calc R U . . .
C32 C 0.1349(4) 0.3829(3) 0.6637(3) 0.0465(8) Uani 1 1 d . . . . .
H32 H 0.2001 0.4433 0.6944 0.056 Uiso 1 1 calc R U . . .
C33 C 0.1400(3) 0.2934(2) 0.5819(2) 0.0336(7) Uani 1 1 d . . . . .
C35 C 0.4526(4) 0.3741(3) 0.6504(3) 0.0485(9) Uani 1 1 d . . . . .
C35' C 0.3486(3) 0.4636(3) 0.5628(3) 0.0530(10) Uani 1 1 d . . . . .
C36 C 0.5529(4) 0.4578(3) 0.6955(3) 0.0465(8) Uani 1 1 d . . . . .
H36 H 0.6234 0.4556 0.7410 0.056 Uiso 1 1 calc R U . . .
C36' C 0.4467(3) 0.5491(3) 0.6074(3) 0.0453(8) Uani 1 1 d . . . . .
H36' H 0.4438 0.6094 0.5929 0.054 Uiso 1 1 calc R U . . .
C37 C 0.5482(3) 0.5449(3) 0.6728(3) 0.0402(8) Uani 1 1 d . . . . .
C38 C 0.5457(6) 0.2849(4) 0.7420(4) 0.0922(18) Uani 1 1 d . . . . .
H38A H 0.6223 0.2824 0.7221 0.138 Uiso 1 1 calc R U . . .
H38B H 0.5275 0.2205 0.7515 0.138 Uiso 1 1 calc R U . . .
H38C H 0.5558 0.3505 0.8030 0.138 Uiso 1 1 calc R U . . .
C40 C 0.6513(4) 0.7159(3) 0.7011(3) 0.0555(10) Uani 1 1 d . . . . .
H40A H 0.6429 0.6916 0.6318 0.083 Uiso 1 1 calc R U . . .
H40B H 0.7294 0.7661 0.7394 0.083 Uiso 1 1 calc R U . . .
H40C H 0.5818 0.7530 0.7182 0.083 Uiso 1 1 calc R U . . .
C41 C 0.1795(3) 0.0221(3) 0.3324(2) 0.0411(8) Uani 1 1 d . . . . .
C42 C 0.2907(3) 0.0299(3) 0.3098(2) 0.0429(8) Uani 1 1 d . . . . .
H42 H 0.3523 0.0921 0.3509 0.052 Uiso 1 1 calc R U . . .
C42' C 0.0921(4) -0.0720(3) 0.2723(3) 0.0538(10) Uani 1 1 d . . . . .
H42' H 0.0162 -0.0801 0.2873 0.065 Uiso 1 1 calc R U . . .
C43 C 0.3140(3) -0.0509(3) 0.2289(3) 0.0448(8) Uani 1 1 d . . . . .
H43 H 0.3904 -0.0445 0.2141 0.054 Uiso 1 1 calc R U . . .
C43' C 0.1142(4) -0.1533(3) 0.1917(3) 0.0520(9) Uani 1 1 d . . . . .
H43' H 0.0544 -0.2170 0.1516 0.062 Uiso 1 1 calc R U . . .
C44 C 0.2238(4) -0.1407(3) 0.1704(2) 0.0439(8) Uani 1 1 d . . . . .
Cl1 Cl -0.0459(7) -0.0642(5) 0.8975(4) 0.1245(15) Uani 0.5 1 d . . P C 1
Cl1B Cl 0.0397(8) -0.0777(6) 0.9281(10) 0.212(4) Uani 0.5 1 d . . P C 2
C49 C 0.0355(18) -0.031(4) 1.021(3) 0.172(11) Uani 0.5 1 d . . P . .
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
C2 O20 C1 113.4(2) . .
C11 O21 C14 117.9(3) . .
C11' O22 C14' 117.3(3) . .
C13 O23 C15 117.6(3) . .
O20 C1 C10 109.7(2) . .
O20 C1 C9 110.5(3) . .
C10 C1 C9 115.5(3) . .
O20 C1 H1 106.9 . .
C10 C1 H1 106.9 . .
C9 C1 H1 106.9 . .
C3 C2 O20 121.6(3) . .
C3 C2 C16 126.2(3) . .
O20 C2 C16 112.2(3) . .
C2 C3 C4 120.8(3) . .
C2 C3 H3 119.6 . .
C4 C3 H3 119.6 . .
C5 C4 C9 119.2(3) . .
C5 C4 C3 124.1(3) . .
C9 C4 C3 116.6(3) . .
C6 C5 C4 120.3(3) . .
C6 C5 H5 119.8 . .
C4 C5 H5 119.8 . .
C5 C6 C7 120.4(3) . .
C5 C6 H6 119.8 . .
C7 C6 H6 119.8 . .
C6 C7 C8 119.8(3) . .
C6 C7 H7 120.1 . .
C8 C7 H7 120.1 . .
C7 C8 C9 120.5(3) . .
C7 C8 H8 119.8 . .
C9 C8 H8 119.8 . .
C8 C9 C4 119.7(3) . .
C8 C9 C1 123.9(3) . .
C4 C9 C1 116.1(3) . .
C11 C10 C11' 117.5(3) . .
C11 C10 C1 124.0(3) . .
C11' C10 C1 118.5(3) . .
O21 C11 C10 115.4(3) . .
O21 C11 C12 122.2(3) . .
C10 C11 C12 122.3(3) . .
O22 C11' C12' 122.7(3) . .
O22 C11' C10 116.1(3) . .
C12' C11' C10 121.2(3) . .
C13 C12 C11 117.7(3) . .
C13 C12 H12 121.2 . .
C11 C12 H12 121.2 . .
C13 C12' C11' 119.1(3) . .
C13 C12' H12' 120.4 . .
C11' C12' H12' 120.4 . .
O23 C13 C12 124.0(3) . .
O23 C13 C12' 113.9(3) . .
C12 C13 C12' 122.1(3) . .
O21 C14 H14A 109.5 . .
O21 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
O21 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
O22 C14' H14D 109.5 . .
O22 C14' H14E 109.5 . .
H14D C14' H14E 109.5 . .
O22 C14' H14F 109.5 . .
H14D C14' H14F 109.5 . .
H14E C14' H14F 109.5 . .
O23 C15 H15A 109.5 . .
O23 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
O23 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C17 C16 C17' 118.3(3) . .
C17 C16 C2 120.1(3) . .
C17' C16 C2 121.5(3) . .
C16 C17 C18 121.0(3) . .
C16 C17 H17 119.5 . .
C18 C17 H17 119.5 . .
C18' C17' C16 121.2(3) . .
C18' C17' H17' 119.4 . .
C16 C17' H17' 119.4 . .
C19 C18 C17 118.8(3) . .
C19 C18 H18 120.6 . .
C17 C18 H18 120.6 . .
C19 C18' C17' 118.8(3) . .
C19 C18' H18' 120.6 . .
C17' C18' H18' 120.6 . .
C18' C19 C18 121.9(3) . .
C18' C19 Br24 119.2(3) . .
C18 C19 Br24 118.9(3) . .
C35 O45 C38 117.8(4) . .
C39 O46 C35' 118.0(7) . .
C35' O46 C39A 117.8(6) . .
C37 O47 C40 117.0(3) . .
C26 O44 C25 105.9(5) . .
O44 C25 C34 108.2(10) . .
O44 C25 C33 110.4(5) . .
C34 C25 C33 115.1(8) . .
O44 C25 H25 107.6 . .
C34 C25 H25 107.6 . .
C33 C25 H25 107.6 . .
C35' C34 C25 121.9(13) . .
C35' C34 C35 114.1(14) . .
C25 C34 C35 122.9(11) . .
O46 C39 H39A 109.5 . .
O46 C39 H39B 109.5 . .
H39A C39 H39B 109.5 . .
O46 C39 H39C 109.5 . .
H39A C39 H39C 109.5 . .
H39B C39 H39C 109.5 . .
C25A O44A C26 113.9(6) . .
O44A C25A C33 114.1(7) . .
O44A C25A C34A 111.7(9) . .
C33 C25A C34A 119.5(9) . .
O44A C25A H25A 103.0 . .
C33 C25A H25A 103.0 . .
C34A C25A H25A 103.0 . .
C35 C34A C25A 120.6(12) . .
C35 C34A C35' 117.7(14) . .
C25A C34A C35' 121.6(10) . .
O46 C39A H39D 109.5 . .
O46 C39A H39E 109.5 . .
H39D C39A H39E 109.5 . .
O46 C39A H39F 109.5 . .
H39D C39A H39F 109.5 . .
H39E C39A H39F 109.5 . .
C27 C26 O44 122.5(4) . .
C27 C26 O44A 116.7(4) . .
C27 C26 C41 127.1(3) . .
O44 C26 C41 108.9(4) . .
O44A C26 C41 115.1(4) . .
C26 C27 C28 121.7(3) . .
C26 C27 H27 119.2 . .
C28 C27 H27 119.2 . .
C29 C28 C33 119.0(3) . .
C29 C28 C27 123.3(3) . .
C33 C28 C27 117.7(3) . .
C30 C29 C28 119.9(4) . .
C30 C29 H29 120.0 . .
C28 C29 H29 120.0 . .
C29 C30 C31 120.4(4) . .
C29 C30 H30 119.8 . .
C31 C30 H30 119.8 . .
C32 C31 C30 120.0(4) . .
C32 C31 H31 120.0 . .
C30 C31 H31 120.0 . .
C31 C32 C33 120.1(3) . .
C31 C32 H32 120.0 . .
C33 C32 H32 120.0 . .
C32 C33 C28 120.6(3) . .
C32 C33 C25A 121.5(4) . .
C28 C33 C25A 116.1(4) . .
C32 C33 C25 124.1(4) . .
C28 C33 C25 113.2(4) . .
C34A C35 O45 110.7(9) . .
C34A C35 C36 126.0(9) . .
O45 C35 C36 123.1(4) . .
O45 C35 C34 118.6(8) . .
C36 C35 C34 118.3(8) . .
C34 C35' O46 109.3(9) . .
C34 C35' C36' 128.3(10) . .
O46 C35' C36' 122.2(4) . .
O46 C35' C34A 120.3(7) . .
C36' C35' C34A 117.4(7) . .
C35 C36 C37 118.6(4) . .
C35 C36 H36 120.7 . .
C37 C36 H36 120.7 . .
C37 C36' C35' 118.7(4) . .
C37 C36' H36' 120.7 . .
C35' C36' H36' 120.7 . .
O47 C37 C36' 124.4(3) . .
O47 C37 C36 114.4(3) . .
C36' C37 C36 121.2(3) . .
O45 C38 H38A 109.5 . .
O45 C38 H38B 109.5 . .
H38A C38 H38B 109.5 . .
O45 C38 H38C 109.5 . .
H38A C38 H38C 109.5 . .
H38B C38 H38C 109.5 . .
O47 C40 H40A 109.5 . .
O47 C40 H40B 109.5 . .
H40A C40 H40B 109.5 . .
O47 C40 H40C 109.5 . .
H40A C40 H40C 109.5 . .
H40B C40 H40C 109.5 . .
C42 C41 C42' 117.9(3) . .
C42 C41 C26 120.6(3) . .
C42' C41 C26 121.5(3) . .
C43 C42 C41 121.6(3) . .
C43 C42 H42 119.2 . .
C41 C42 H42 119.2 . .
C43' C42' C41 121.1(3) . .
C43' C42' H42' 119.4 . .
C41 C42' H42' 119.4 . .
C44 C43 C42 118.4(3) . .
C44 C43 H43 120.8 . .
C42 C43 H43 120.8 . .
C44 C43' C42' 119.0(3) . .
C44 C43' H43' 120.5 . .
C42' C43' H43' 120.5 . .
C43' C44 C43 121.9(3) . .
C43' C44 Br48 119.1(3) . .
C43 C44 Br48 119.0(3) . .
C49 Cl1 C49 52.5(14) 2_557 .
C49 Cl1B C49 54.6(13) . 2_557
Cl1B C49 C49 76(3) . 2_557
Cl1 C49 C49 79(4) 2_557 2_557
Cl1B C49 Cl1B 125.4(13) . 2_557
C49 C49 Cl1B 49(2) 2_557 2_557
Cl1 C49 Cl1 127.5(14) 2_557 .
C49 C49 Cl1 48(3) 2_557 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br24 C19 1.902(3) .
O20 C2 1.376(4) .
O20 C1 1.450(4) .
O21 C11 1.364(4) .
O21 C14 1.426(4) .
O22 C11' 1.369(4) .
O22 C14' 1.424(5) .
O23 C13 1.374(4) .
O23 C15 1.421(4) .
C1 C10 1.507(4) .
C1 C9 1.515(4) .
C1 H1 1.0000 .
C2 C3 1.333(5) .
C2 C16 1.474(4) .
C3 C4 1.459(4) .
C3 H3 0.9500 .
C4 C5 1.396(5) .
C4 C9 1.401(4) .
C5 C6 1.380(5) .
C5 H5 0.9500 .
C6 C7 1.382(5) .
C6 H6 0.9500 .
C7 C8 1.386(5) .
C7 H7 0.9500 .
C8 C9 1.387(4) .
C8 H8 0.9500 .
C10 C11 1.386(4) .
C10 C11' 1.406(5) .
C11 C12 1.400(4) .
C11' C12' 1.382(5) .
C12 C13 1.378(4) .
C12 H12 0.9500 .
C12' C13 1.380(5) .
C12' H12' 0.9500 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C14' H14D 0.9800 .
C14' H14E 0.9800 .
C14' H14F 0.9800 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 C17 1.388(5) .
C16 C17' 1.397(5) .
C17 C18 1.390(5) .
C17 H17 0.9500 .
C17' C18' 1.381(5) .
C17' H17' 0.9500 .
C18 C19 1.375(5) .
C18 H18 0.9500 .
C18' C19 1.374(5) .
C18' H18' 0.9500 .
Br48 C44 1.903(3) .
O45 C35 1.361(5) .
O45 C38 1.409(6) .
O46 C39 1.268(16) .
O46 C35' 1.369(5) .
O46 C39A 1.599(12) .
O47 C37 1.366(4) .
O47 C40 1.435(4) .
O44 C26 1.396(8) .
O44 C25 1.495(10) .
C25 C34 1.51(2) .
C25 C33 1.569(8) .
C25 H25 1.0000 .
C34 C35' 1.226(18) .
C34 C35 1.593(14) .
C39 H39A 0.9800 .
C39 H39B 0.9800 .
C39 H39C 0.9800 .
O44A C25A 1.397(12) .
O44A C26 1.423(8) .
C25A C33 1.421(8) .
C25A C34A 1.52(2) .
C25A H25A 1.0000 .
C34A C35 1.202(17) .
C34A C35' 1.564(15) .
C39A H39D 0.9800 .
C39A H39E 0.9800 .
C39A H39F 0.9800 .
C26 C27 1.329(5) .
C26 C41 1.472(5) .
C27 C28 1.450(5) .
C27 H27 0.9500 .
C28 C29 1.383(5) .
C28 C33 1.399(4) .
C29 C30 1.382(6) .
C29 H29 0.9500 .
C30 C31 1.385(6) .
C30 H30 0.9500 .
C31 C32 1.369(6) .
C31 H31 0.9500 .
C32 C33 1.373(5) .
C32 H32 0.9500 .
C35 C36 1.386(5) .
C35' C36' 1.385(5) .
C36 C37 1.391(5) .
C36 H36 0.9500 .
C36' C37 1.373(5) .
C36' H36' 0.9500 .
C38 H38A 0.9800 .
C38 H38B 0.9800 .
C38 H38C 0.9800 .
C40 H40A 0.9800 .
C40 H40B 0.9800 .
C40 H40C 0.9800 .
C41 C42 1.388(5) .
C41 C42' 1.399(5) .
C42 C43 1.384(5) .
C42 H42 0.9500 .
C42' C43' 1.378(5) .
C42' H42' 0.9500 .
C43 C44 1.377(5) .
C43 H43 0.9500 .
C43' C44 1.372(5) .
C43' H43' 0.9500 .
Cl1 C49 1.37(5) 2_557
Cl1 C49 1.80(4) .
Cl1B C49 1.35(4) .
Cl1B C49 1.74(4) 2_557
C49 Cl1 1.37(5) 2_557
C49 C49 1.46(3) 2_557
C49 Cl1B 1.74(4) 2_557
