#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/71/7117191.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_7117191
loop_
_publ_author_name
'Wu-Lin Yang'
'Yang-Zi Liu'
'Shuai Luo'
'Xingxin Yu'
'John S. Fossey'
'Wei-Ping Deng'
_publ_section_title
;
 The copper-catalyzed asymmetric construction of a dispiropyrrolidine
 skeleton via 1,3-dipolar cycloaddition of azomethine ylides to
 alpha-alkylidene succinimides
;
_journal_name_full               Chem.Commun.
_journal_page_first              9212
_journal_paper_doi               10.1039/C5cc02362A
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C22 H19 Br Cl3 N2 O4'
_chemical_formula_weight         561.65
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-08-18 deposited with the CCDC.
2015-04-28 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2175(12)
_cell_length_b                   12.1386(14)
_cell_length_c                   19.641(2)
_cell_measurement_reflns_used    3494
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      43.449
_cell_measurement_theta_min      4.494
_cell_volume                     2436.0(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0401
_diffrn_reflns_av_sigmaI/netI    0.0516
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14495
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    2.047
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.19441
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1132
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.123
_refine_diff_density_max         0.548
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.024(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         4791
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0877
_refine_ls_R_factor_gt           0.0638
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1266P)²+0.3493P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1817
_refine_ls_wR_factor_ref         0.1980
_reflns_number_gt                3397
_reflns_number_total             4791
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc02362a2.cif
_cod_data_source_block           cd21432
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7117191
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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 0.97584(7) 0.19097(8) 0.92503(4) 0.0961(4) Uani 1 1 d . . .
Cl1 Cl 0.2528(8) 0.1479(5) 0.54840(18) 0.248(3) Uani 1 1 d . . .
Cl2 Cl 0.4024(7) 0.1198(6) 0.4334(4) 0.295(4) Uani 1 1 d . . .
Cl3 Cl 0.1693(7) 0.2391(4) 0.4232(3) 0.233(3) Uani 1 1 d . . .
N1 N 0.3755(4) 0.1263(4) 0.8117(2) 0.0442(9) Uani 1 1 d . . .
N2 N 0.5011(4) 0.4187(3) 0.7138(2) 0.0429(9) Uani 1 1 d . . .
O1 O 0.4339(4) 0.1776(3) 0.70414(17) 0.0546(9) Uani 1 1 d . . .
O2 O 0.3048(5) 0.1202(3) 0.9220(2) 0.0702(12) Uani 1 1 d . . .
O3 O 0.2386(13) 0.4133(11) 0.5963(6) 0.099(3) Uani 0.60 1 d PDU A 1
O4 O 0.4238(9) 0.5110(8) 0.5876(3) 0.092(2) Uani 0.70 1 d PDU A 1
C21 C 0.3996(15) 0.5366(13) 0.5168(5) 0.101(3) Uani 0.70 1 d PDU A 1
H21A H 0.4489 0.4900 0.4868 0.152 Uiso 0.70 1 d PR A 1
H21B H 0.4218 0.6122 0.5083 0.152 Uiso 0.70 1 d PR A 1
H21C H 0.3078 0.5257 0.5089 0.152 Uiso 0.70 1 d PR A 1
O3' O 0.2471(19) 0.4796(16) 0.5937(9) 0.099(4) Uani 0.40 1 d PDU A 2
O4' O 0.4517(17) 0.4317(19) 0.5815(8) 0.099(3) Uani 0.30 1 d PDU A 2
C21' C 0.393(3) 0.461(3) 0.5142(11) 0.104(4) Uani 0.30 1 d PDU A 2
H21D H 0.3275 0.5168 0.5203 0.157 Uiso 0.30 1 d PR A 2
H21E H 0.3530 0.3968 0.4939 0.157 Uiso 0.30 1 d PR A 2
H21F H 0.4606 0.4877 0.4849 0.157 Uiso 0.30 1 d PR A 2
C1 C 0.3942(4) 0.2008(4) 0.7611(2) 0.0390(10) Uani 1 1 d . . .
C2 C 0.3278(5) 0.1702(4) 0.8703(2) 0.0467(11) Uani 1 1 d . . .
C3 C 0.3051(5) 0.2923(4) 0.8582(3) 0.0480(12) Uani 1 1 d . . .
H3A H 0.3507 0.3361 0.8920 0.058 Uiso 1 1 calc R . .
H3B H 0.2125 0.3096 0.8602 0.058 Uiso 1 1 calc R . .
C4 C 0.3598(4) 0.3145(4) 0.7868(2) 0.0407(10) Uani 1 1 d . . .
C5 C 0.2693(5) 0.3749(4) 0.7339(3) 0.0485(12) Uani 1 1 d . . .
H5 H 0.2365 0.3195 0.7019 0.058 Uiso 1 1 calc R . .
C6 C 0.3666(5) 0.4512(4) 0.6945(3) 0.0462(11) Uani 1 1 d . A .
H6 H 0.3530 0.5263 0.7114 0.055 Uiso 1 1 calc R . .
C7 C 0.4877(5) 0.3869(4) 0.7852(2) 0.0415(10) Uani 1 1 d . . .
H7 H 0.4679 0.4544 0.8105 0.050 Uiso 1 1 calc R . .
C8 C 0.6085(5) 0.3382(4) 0.8172(2) 0.0440(11) Uani 1 1 d . . .
C9 C 0.6925(5) 0.2676(4) 0.7825(3) 0.0511(12) Uani 1 1 d . . .
H9 H 0.6754 0.2492 0.7374 0.061 Uiso 1 1 calc R . .
C10 C 0.8023(5) 0.2246(5) 0.8152(3) 0.0570(13) Uani 1 1 d . . .
H10 H 0.8595 0.1788 0.7917 0.068 Uiso 1 1 calc R . .
C11 C 0.8256(6) 0.2503(5) 0.8824(3) 0.0611(14) Uani 1 1 d . . .
C12 C 0.7432(6) 0.3185(7) 0.9169(3) 0.0752(17) Uani 1 1 d . . .
H12 H 0.7601 0.3363 0.9621 0.090 Uiso 1 1 calc R . .
C13 C 0.6348(6) 0.3612(6) 0.8847(3) 0.0632(15) Uani 1 1 d . . .
H13 H 0.5780 0.4064 0.9089 0.076 Uiso 1 1 calc R . .
C14 C 0.1556(6) 0.4371(4) 0.7601(3) 0.0618(15) Uani 1 1 d . . .
C15 C 0.1657(7) 0.5166(6) 0.8140(4) 0.0743(18) Uani 1 1 d . . .
H15 H 0.2464 0.5297 0.8343 0.089 Uiso 1 1 calc R . .
C16 C 0.0561(10) 0.5742(7) 0.8360(5) 0.108(3) Uani 1 1 d . . .
H16 H 0.0646 0.6246 0.8713 0.129 Uiso 1 1 calc R . .
C17 C -0.0600(9) 0.5590(10) 0.8079(7) 0.133(5) Uani 1 1 d . . .
H17 H -0.1323 0.5978 0.8239 0.159 Uiso 1 1 calc R . .
C18 C -0.0744(8) 0.4805(10) 0.7513(7) 0.119(4) Uani 1 1 d . . .
H18 H -0.1540 0.4719 0.7291 0.143 Uiso 1 1 calc R . .
C19 C 0.0309(7) 0.4216(6) 0.7328(5) 0.092(2) Uani 1 1 d . . .
H19 H 0.0201 0.3673 0.6999 0.111 Uiso 1 1 calc R . .
C20 C 0.3412(8) 0.4533(5) 0.6197(3) 0.079(2) Uani 1 1 d D . .
C22 C 0.2492(11) 0.1304(8) 0.4648(5) 0.108(3) Uani 1 1 d . . .
H22 H 0.2022 0.0618 0.4549 0.129 Uiso 1 1 calc R . .
H2 H 0.512(5) 0.358(4) 0.690(2) 0.031(11) Uiso 1 1 d . . .
H1 H 0.385(5) 0.061(5) 0.812(2) 0.033(13) Uiso 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'
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'
Cl Cl 0.1484 0.1585 '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
C1 N1 C2 114.2(4) . .
C1 N1 H1 131(3) . .
C2 N1 H1 115(3) . .
C7 N2 C6 103.2(4) . .
C7 N2 H2 107(3) . .
C6 N2 H2 102(3) . .
C20 O4 C21 118.9(8) . .
O4 C21 H21A 112.0 . .
O4 C21 H21B 109.4 . .
H21A C21 H21B 109.5 . .
O4 C21 H21C 107.0 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
O4 C21 H21D 90.5 . .
H21A C21 H21D 111.7 . .
H21B C21 H21D 122.3 . .
H21C C21 H21D 17.6 . .
O4 C21 H21F 110.2 . .
H21A C21 H21F 4.2 . .
H21B C21 H21F 107.1 . .
H21C C21 H21F 113.7 . .
H21D C21 H21F 115.8 . .
C20 O4' C21' 96.1(17) . .
O4' C21' H21A 112.2 . .
O4' C21' H21C 122.2 . .
H21A C21' H21C 99.1 . .
O4' C21' H21D 109.6 . .
H21A C21' H21D 104.3 . .
H21C C21' H21D 12.7 . .
O4' C21' H21E 110.3 . .
H21A C21' H21E 110.8 . .
H21C C21' H21E 101.3 . .
H21D C21' H21E 109.5 . .
O4' C21' H21F 108.5 . .
H21A C21' H21F 5.4 . .
H21C C21' H21F 104.5 . .
H21D C21' H21F 109.5 . .
H21E C21' H21F 109.5 . .
O1 C1 N1 124.3(4) . .
O1 C1 C4 126.3(4) . .
N1 C1 C4 109.4(4) . .
O2 C2 N1 125.8(5) . .
O2 C2 C3 126.4(5) . .
N1 C2 C3 107.8(4) . .
C2 C3 C4 105.0(4) . .
C2 C3 H3A 110.7 . .
C4 C3 H3A 110.7 . .
C2 C3 H3B 110.7 . .
C4 C3 H3B 110.7 . .
H3A C3 H3B 108.8 . .
C1 C4 C3 103.3(4) . .
C1 C4 C5 110.0(4) . .
C3 C4 C5 118.1(4) . .
C1 C4 C7 108.1(4) . .
C3 C4 C7 114.7(4) . .
C5 C4 C7 102.4(4) . .
C14 C5 C6 111.7(4) . .
C14 C5 C4 118.1(5) . .
C6 C5 C4 103.3(4) . .
C14 C5 H5 107.8 . .
C6 C5 H5 107.8 . .
C4 C5 H5 107.8 . .
N2 C6 C20 114.7(5) . .
N2 C6 C5 107.8(4) . .
C20 C6 C5 112.8(5) . .
N2 C6 H6 107.0 . .
C20 C6 H6 107.0 . .
C5 C6 H6 107.0 . .
N2 C7 C8 115.3(4) . .
N2 C7 C4 104.2(4) . .
C8 C7 C4 116.9(4) . .
N2 C7 H7 106.6 . .
C8 C7 H7 106.6 . .
C4 C7 H7 106.6 . .
C13 C8 C9 118.3(5) . .
C13 C8 C7 118.7(4) . .
C9 C8 C7 122.9(4) . .
C8 C9 C10 120.1(5) . .
C8 C9 H9 120.0 . .
C10 C9 H9 120.0 . .
C11 C10 C9 119.8(5) . .
C11 C10 H10 120.1 . .
C9 C10 H10 120.1 . .
C12 C11 C10 120.5(5) . .
C12 C11 Br1 120.9(5) . .
C10 C11 Br1 118.6(5) . .
C11 C12 C13 119.9(5) . .
C11 C12 H12 120.1 . .
C13 C12 H12 120.1 . .
C12 C13 C8 121.4(6) . .
C12 C13 H13 119.3 . .
C8 C13 H13 119.3 . .
C19 C14 C15 116.0(6) . .
C19 C14 C5 121.1(6) . .
C15 C14 C5 122.9(5) . .
C16 C15 C14 120.6(8) . .
C16 C15 H15 119.7 . .
C14 C15 H15 119.7 . .
C17 C16 C15 121.6(11) . .
C17 C16 H16 119.2 . .
C15 C16 H16 119.2 . .
C16 C17 C18 119.6(8) . .
C16 C17 H17 120.2 . .
C18 C17 H17 120.2 . .
C19 C18 C17 118.0(9) . .
C19 C18 H18 121.0 . .
C17 C18 H18 121.0 . .
C18 C19 C14 123.8(10) . .
C18 C19 H19 118.1 . .
C14 C19 H19 118.1 . .
O3' C20 O3 39.5(9) . .
O3' C20 O4 100.7(13) . .
O3 C20 O4 126.5(9) . .
O3' C20 O4' 120.1(14) . .
O3 C20 O4' 114.5(11) . .
O4 C20 O4' 44.7(9) . .
O3' C20 C6 126.5(12) . .
O3 C20 C6 120.2(9) . .
O4 C20 C6 112.6(6) . .
O4' C20 C6 112.9(9) . .
Cl1 C22 Cl2 110.6(8) . .
Cl1 C22 Cl3 112.1(6) . .
Cl2 C22 Cl3 108.5(6) . .
Cl1 C22 H22 108.5 . .
Cl2 C22 H22 108.5 . .
Cl3 C22 H22 108.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C11 1.891(6) .
Cl1 C22 1.656(11) .
Cl2 C22 1.687(11) .
Cl3 C22 1.754(11) .
N1 C1 1.357(6) .
N1 C2 1.359(7) .
N1 H1 0.80(6) .
N2 C7 1.461(6) .
N2 C6 1.480(7) .
N2 H2 0.87(5) .
O1 C1 1.223(6) .
O2 C2 1.205(6) .
O3 C20 1.243(12) .
O4 C20 1.264(9) .
O4 C21 1.447(11) .
C21 H21A 0.9600 .
C21 H21B 0.9600 .
C21 H21C 0.9600 .
C21 H21D 0.7784 .
C21 H21F 1.0634 .
O3' C20 1.135(14) .
O4' C20 1.380(16) .
O4' C21' 1.495(18) .
C21' H21A 0.8656 .
C21' H21C 1.1773 .
C21' H21D 0.9600 .
C21' H21E 0.9600 .
C21' H21F 0.9600 .
C1 C4 1.511(7) .
C2 C3 1.519(7) .
C3 C4 1.533(6) .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C4 C5 1.572(7) .
C4 C7 1.575(6) .
C5 C14 1.477(8) .
C5 C6 1.564(7) .
C5 H5 0.9800 .
C6 C20 1.493(8) .
C6 H6 0.9800 .
C7 C8 1.507(7) .
C7 H7 0.9800 .
C8 C13 1.381(8) .
C8 C9 1.391(7) .
C9 C10 1.393(8) .
C9 H9 0.9300 .
C10 C11 1.377(8) .
C10 H10 0.9300 .
C11 C12 1.362(9) .
C12 C13 1.376(9) .
C12 H12 0.9300 .
C13 H13 0.9300 .
C14 C19 1.395(10) .
C14 C15 1.436(10) .
C15 C16 1.389(10) .
C15 H15 0.9300 .
C16 C17 1.320(17) .
C16 H16 0.9300 .
C17 C18 1.472(17) .
C17 H17 0.9300 .
C18 C19 1.341(13) .
C18 H18 0.9300 .
C19 H19 0.9300 .
C22 H22 0.9800 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 Cl3 0.87(5) 2.99(5) 3.723(6) 143(4) 4_556
N2 H2 O1 0.87(5) 2.35(5) 3.012(5) 133(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C2 N1 C1 O1 -178.5(5) . . . .
C2 N1 C1 C4 2.1(5) . . . .
C1 N1 C2 O2 -179.3(5) . . . .
C1 N1 C2 C3 2.3(6) . . . .
O2 C2 C3 C4 176.0(5) . . . .
N1 C2 C3 C4 -5.7(6) . . . .
O1 C1 C4 C3 175.1(4) . . . .
N1 C1 C4 C3 -5.5(5) . . . .
O1 C1 C4 C5 48.1(6) . . . .
N1 C1 C4 C5 -132.5(4) . . . .
O1 C1 C4 C7 -62.9(6) . . . .
N1 C1 C4 C7 116.5(4) . . . .
C2 C3 C4 C1 6.5(5) . . . .
C2 C3 C4 C5 128.2(4) . . . .
C2 C3 C4 C7 -110.9(4) . . . .
C1 C4 C5 C14 136.8(4) . . . .
C3 C4 C5 C14 18.6(6) . . . .
C7 C4 C5 C14 -108.5(5) . . . .
C1 C4 C5 C6 -99.4(4) . . . .
C3 C4 C5 C6 142.4(4) . . . .
C7 C4 C5 C6 15.3(5) . . . .
C7 N2 C6 C20 -161.3(4) . . . .
C7 N2 C6 C5 -34.7(5) . . . .
C14 C5 C6 N2 138.7(5) . . . .
C4 C5 C6 N2 10.7(5) . . . .
C14 C5 C6 C20 -93.6(6) . . . .
C4 C5 C6 C20 138.4(5) . . . .
C6 N2 C7 C8 174.0(4) . . . .
C6 N2 C7 C4 44.5(4) . . . .
C1 C4 C7 N2 78.9(4) . . . .
C3 C4 C7 N2 -166.5(4) . . . .
C5 C4 C7 N2 -37.2(4) . . . .
C1 C4 C7 C8 -49.5(5) . . . .
C3 C4 C7 C8 65.1(5) . . . .
C5 C4 C7 C8 -165.7(4) . . . .
N2 C7 C8 C13 144.4(5) . . . .
C4 C7 C8 C13 -92.7(6) . . . .
N2 C7 C8 C9 -38.1(6) . . . .
C4 C7 C8 C9 84.8(6) . . . .
C13 C8 C9 C10 -1.9(7) . . . .
C7 C8 C9 C10 -179.5(5) . . . .
C8 C9 C10 C11 1.4(8) . . . .
C9 C10 C11 C12 -0.9(9) . . . .
C9 C10 C11 Br1 -179.7(4) . . . .
C10 C11 C12 C13 0.8(10) . . . .
Br1 C11 C12 C13 179.7(5) . . . .
C11 C12 C13 C8 -1.4(11) . . . .
C9 C8 C13 C12 1.9(9) . . . .
C7 C8 C13 C12 179.6(6) . . . .
C6 C5 C14 C19 110.5(6) . . . .
C4 C5 C14 C19 -129.9(6) . . . .
C6 C5 C14 C15 -69.0(7) . . . .
C4 C5 C14 C15 50.5(7) . . . .
C19 C14 C15 C16 -0.6(9) . . . .
C5 C14 C15 C16 179.0(6) . . . .
C14 C15 C16 C17 -0.8(12) . . . .
C15 C16 C17 C18 -0.8(13) . . . .
C16 C17 C18 C19 4.0(13) . . . .
C17 C18 C19 C14 -5.7(13) . . . .
C15 C14 C19 C18 4.0(11) . . . .
C5 C14 C19 C18 -175.5(7) . . . .
C21 O4 C20 O3' -32.2(16) . . . .
C21 O4 C20 O3 1.0(18) . . . .
C21 O4 C20 O4' 90.1(15) . . . .
C21 O4 C20 C6 -169.5(10) . . . .
C21' O4' C20 O3' 2(3) . . . .
C21' O4' C20 O3 47(2) . . . .
C21' O4' C20 O4 -71.2(19) . . . .
C21' O4' C20 C6 -170.7(16) . . . .
N2 C6 C20 O3' -176.9(15) . . . .
C5 C6 C20 O3' 59.1(16) . . . .
N2 C6 C20 O3 135.9(10) . . . .
C5 C6 C20 O3 11.9(12) . . . .
N2 C6 C20 O4 -53.0(9) . . . .
C5 C6 C20 O4 -176.9(7) . . . .
N2 C6 C20 O4' -4.3(12) . . . .
C5 C6 C20 O4' -128.2(12) . . . .
