#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/36/4083662.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_4083662
loop_
_publ_author_name
'Mustafizur Rahman, A. F. M.'
'Murafuji, Toshihiro'
'Shibasaki, Toshihisa'
'Suetake, Kouichi'
'Kurotobi, Kei'
'Sugihara, Yoshikazu'
'Azuma, Nagao'
'Mikata, Yuji'
_publ_section_title
;
 Characterization of Azulenylphosphine Derivatives. Unexpected
 Debromination and Its Synthetic Utility in the Preparation of
 2-Substituted Azulene
;
_journal_issue                   12
_journal_name_full               Organometallics
_journal_page_first              2971
_journal_paper_doi               10.1021/om0607090
_journal_volume                  26
_journal_year                    2007
_chemical_formula_moiety         'C22 H16 Br O P '
_chemical_formula_sum            'C22 H16 Br O P'
_chemical_formula_weight         407.25
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_cell_angle_alpha                90
_cell_angle_beta                 95.740(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.984(5)
_cell_length_b                   9.519(5)
_cell_length_c                   18.881(10)
_cell_measurement_reflns_used    3018
_cell_measurement_temperature    173.1
_cell_measurement_theta_max      28.7
_cell_measurement_theta_min      2.1
_cell_volume                     1785.4(16)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.6.0'
_computing_structure_refinement  SHELXL
_computing_structure_solution    SHELXS97
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.9904
_diffrn_measured_fraction_theta_max 0.9816
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       omega
_diffrn_radiation_type           'Mo Kalpha'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.050
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            15194
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         28.70
_exptl_absorpt_coefficient_mu    2.405
_exptl_absorpt_correction_T_max  0.825
_exptl_absorpt_correction_T_min  0.586
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       unknown
_exptl_crystal_F_000             824.00
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.79
_refine_diff_density_min         -0.49
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.955
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4072
_refine_ls_R_factor_gt           0.0460
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[sigma²(Fo²)+(0.0418P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1100
_reflns_number_gt                1765
_reflns_number_total             4546
_reflns_threshold_expression     F²>2.0sigma(F²)
_cod_data_source_file            om0607090-file003.cif
_cod_data_source_block           '__AzureneCT-050520_Compound_9'
_cod_original_cell_volume        1785.5(16)
_cod_original_formula_sum        'C22 H16 Br O P '
_cod_database_code               4083662
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 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
Br(1) Br 0.20603(4) 0.90907(4) 0.10240(2) 0.0414(2) Uani 1.00 1 d .
P(1) P 0.40759(9) 0.61274(10) 0.16229(5) 0.0247(2) Uani 1.00 1 d .
O(1) O 0.3525(2) 0.6567(3) 0.22888(13) 0.0311(6) Uani 1.00 1 d .
C(1) C 0.2088(4) 0.7321(4) 0.0584(2) 0.0279(9) Uani 1.00 1 d .
C(2) C 0.2897(3) 0.6180(4) 0.0846(2) 0.0228(8) Uani 1.00 1 d .
C(3) C 0.2610(3) 0.5066(4) 0.0375(2) 0.0255(9) Uani 1.00 1 d .
C(4) C 0.1213(4) 0.4643(4) -0.0747(2) 0.0293(9) Uani 1.00 1 d .
C(5) C 0.0362(4) 0.4987(4) -0.1349(2) 0.0342(10) Uani 1.00 1 d .
C(6) C -0.0247(4) 0.6257(4) -0.1517(2) 0.0340(10) Uani 1.00 1 d .
C(7) C -0.0217(4) 0.7509(4) -0.1131(2) 0.0342(10) Uani 1.00 1 d .
C(8) C 0.0457(4) 0.7819(4) -0.0478(2) 0.0307(9) Uani 1.00 1 d .
C(9) C 0.1322(3) 0.6957(4) -0.0047(2) 0.0245(8) Uani 1.00 1 d .
C(10) C 0.1669(3) 0.5476(4) -0.0179(2) 0.0236(8) Uani 1.00 1 d .
C(11) C 0.5482(4) 0.7198(4) 0.1411(2) 0.0275(9) Uani 1.00 1 d .
C(12) C 0.5587(4) 0.7760(4) 0.0745(2) 0.0327(9) Uani 1.00 1 d .
C(13) C 0.6684(4) 0.8607(4) 0.0619(3) 0.0428(11) Uani 1.00 1 d .
C(14) C 0.7664(4) 0.8876(4) 0.1174(3) 0.0452(12) Uani 1.00 1 d .
C(15) C 0.7573(4) 0.8311(4) 0.1831(3) 0.0435(12) Uani 1.00 1 d .
C(16) C 0.6490(4) 0.7481(4) 0.1958(2) 0.0353(10) Uani 1.00 1 d .
C(17) C 0.4624(4) 0.4330(4) 0.1646(2) 0.0244(8) Uani 1.00 1 d .
C(18) C 0.5665(4) 0.3853(4) 0.1270(2) 0.0320(9) Uani 1.00 1 d .
C(19) C 0.5953(4) 0.2426(4) 0.1260(2) 0.0372(10) Uani 1.00 1 d .
C(20) C 0.5211(4) 0.1483(4) 0.1615(2) 0.0359(10) Uani 1.00 1 d .
C(21) C 0.4187(4) 0.1954(4) 0.1985(2) 0.0334(10) Uani 1.00 1 d .
C(22) C 0.3897(4) 0.3371(4) 0.2013(2) 0.0272(9) Uani 1.00 1 d .
H(1) H 0.2993 0.4176 0.0425 0.031 Uiso 1.00 1 c R
H(2) H 0.1517 0.3719 -0.0725 0.035 Uiso 1.00 1 c R
H(3) H 0.0181 0.4270 -0.1679 0.041 Uiso 1.00 1 c R
H(4) H -0.0758 0.6285 -0.1956 0.041 Uiso 1.00 1 c R
H(5) H -0.0726 0.8239 -0.1346 0.041 Uiso 1.00 1 c R
H(6) H 0.0318 0.8715 -0.0303 0.037 Uiso 1.00 1 c R
H(7) H 0.4922 0.7574 0.0376 0.039 Uiso 1.00 1 c R
H(8) H 0.6753 0.8983 0.0170 0.051 Uiso 1.00 1 c R
H(9) H 0.8391 0.9447 0.1098 0.054 Uiso 1.00 1 c R
H(10) H 0.8247 0.8487 0.2196 0.052 Uiso 1.00 1 c R
H(11) H 0.6432 0.7110 0.2410 0.042 Uiso 1.00 1 c R
H(12) H 0.3217 0.3684 0.2277 0.033 Uiso 1.00 1 c R
H(13) H 0.3682 0.1314 0.2218 0.040 Uiso 1.00 1 c R
H(14) H 0.5406 0.0528 0.1603 0.043 Uiso 1.00 1 c R
H(15) H 0.6652 0.2104 0.1013 0.045 Uiso 1.00 1 c R
H(16) H 0.6163 0.4484 0.1027 0.038 Uiso 1.00 1 c R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
Br Br -0.290 2.459
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
P P 0.102 0.094
;
International Tables for Crystallography
(1992, 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
Br(1) C(1) C(2) 124.6(3)
Br(1) C(1) C(9) 124.7(3)
C(2) P(1) O(1) 114.8(2)
C(11) P(1) O(1) 113.0(2)
C(17) P(1) O(1) 112.8(2)
P(1) C(2) C(1) 127.9(3)
P(1) C(2) C(3) 125.3(3)
C(11) P(1) C(2) 105.3(2)
C(17) P(1) C(2) 102.7(2)
P(1) C(11) C(12) 123.4(3)
P(1) C(11) C(16) 117.6(3)
C(17) P(1) C(11) 107.4(2)
P(1) C(17) C(18) 122.7(3)
P(1) C(17) C(22) 117.6(3)
C(9) C(1) C(2) 110.7(3)
C(1) C(2) C(3) 106.7(3)
C(1) C(9) C(8) 127.4(3)
C(1) C(9) C(10) 105.3(3)
C(2) C(3) C(10) 110.3(3)
C(3) C(10) C(9) 107.0(3)
C(3) C(10) C(4) 124.9(3)
C(10) C(4) C(5) 129.1(4)
C(4) C(5) C(6) 128.1(4)
C(4) C(10) C(9) 128.1(3)
C(5) C(6) C(7) 130.0(4)
C(6) C(7) C(8) 129.4(4)
C(7) C(8) C(9) 128.0(4)
C(8) C(9) C(10) 127.3(3)
C(16) C(11) C(12) 119.1(3)
C(11) C(12) C(13) 120.6(4)
C(11) C(16) C(15) 120.1(4)
C(12) C(13) C(14) 119.0(4)
C(13) C(14) C(15) 120.6(4)
C(14) C(15) C(16) 120.6(4)
C(22) C(17) C(18) 119.5(3)
C(17) C(18) C(19) 119.5(4)
C(17) C(22) C(21) 119.9(4)
C(18) C(19) C(20) 120.5(4)
C(19) C(20) C(21) 119.9(4)
C(20) C(21) C(22) 120.7(4)
C(2) C(3) H(1) 124.8580
H(1) C(3) C(10) 124.8632
H(2) C(4) C(5) 115.4431
C(4) C(5) H(3) 115.9698
H(2) C(4) C(10) 115.4474
H(3) C(5) C(6) 115.9668
C(5) C(6) H(4) 114.9924
H(4) C(6) C(7) 114.9897
C(6) C(7) H(5) 115.3013
C(7) C(8) H(6) 116.0175
H(5) C(7) C(8) 115.3058
H(6) C(8) C(9) 116.0105
C(11) C(12) H(7) 119.6916
C(11) C(16) H(11) 119.9693
H(7) C(12) C(13) 119.6964
C(12) C(13) H(8) 120.4921
H(8) C(13) C(14) 120.4968
C(13) C(14) H(9) 119.7071
C(14) C(15) H(10) 119.6702
H(9) C(14) C(15) 119.6986
C(15) C(16) H(11) 119.9666
H(10) C(15) C(16) 119.6827
C(17) C(18) H(16) 120.2472
C(17) C(22) H(12) 120.0673
H(16) C(18) C(19) 120.2456
C(18) C(19) H(15) 119.7457
H(15) C(19) C(20) 119.7474
C(19) C(20) H(14) 120.0296
C(20) C(21) H(13) 119.6668
H(14) C(20) C(21) 120.0411
C(21) C(22) H(12) 120.0521
H(13) C(21) C(22) 119.6827
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br(1) C(1) 1.880(4)
P(1) O(1) 1.482(3)
P(1) C(2) 1.787(3)
P(1) C(11) 1.812(4)
P(1) C(17) 1.796(4)
C(1) C(2) 1.413(5)
C(1) C(9) 1.394(5)
C(2) C(3) 1.395(5)
C(3) C(10) 1.390(5)
C(4) C(5) 1.388(5)
C(4) C(10) 1.374(5)
C(5) C(6) 1.376(6)
C(6) C(7) 1.396(6)
C(7) C(8) 1.376(5)
C(8) C(9) 1.393(5)
C(9) C(10) 1.479(5)
C(11) C(12) 1.381(6)
C(11) C(16) 1.394(5)
C(12) C(13) 1.399(6)
C(13) C(14) 1.384(6)
C(14) C(15) 1.363(7)
C(15) C(16) 1.380(6)
C(17) C(18) 1.392(5)
C(17) C(22) 1.394(5)
C(18) C(19) 1.389(5)
C(19) C(20) 1.380(6)
C(20) C(21) 1.370(6)
C(21) C(22) 1.382(5)
C(3) H(1) 0.9300
C(4) H(2) 0.9300
C(5) H(3) 0.9300
C(6) H(4) 0.9299
C(7) H(5) 0.9300
C(8) H(6) 0.9300
C(12) H(7) 0.9300
C(13) H(8) 0.9301
C(14) H(9) 0.9300
C(15) H(10) 0.9300
C(16) H(11) 0.9298
C(18) H(16) 0.9299
C(19) H(15) 0.9299
C(20) H(14) 0.9300
C(21) H(13) 0.9300
C(22) H(12) 0.9300
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
Br(1) P(1) 3.582(1) .
Br(1) O(1) 3.594(2) .
Br(1) C(2) 2.923(3) .
Br(1) C(8) 3.341(4) .
Br(1) C(9) 2.909(4) .
P(1) C(1) 2.880(4) .
P(1) C(3) 2.833(4) .
P(1) C(12) 2.818(4) .
P(1) C(16) 2.750(4) .
P(1) C(18) 2.804(4) .
P(1) C(22) 2.737(4) .
O(1) C(1) 3.465(4) .
O(1) C(2) 2.758(4) .
O(1) C(6) 3.213(5) 56504
O(1) C(7) 3.242(4) 56504
O(1) C(11) 2.752(5) .
O(1) C(16) 3.206(5) .
O(1) C(17) 2.735(4) .
O(1) C(21) 3.177(5) 55502
O(1) C(22) 3.115(5) .
O(1) C(22) 3.342(5) 55502
C(1) C(3) 2.253(5) .
C(1) C(8) 2.499(5) .
C(1) C(10) 2.284(5) .
C(1) C(11) 3.589(5) .
C(1) C(12) 3.501(5) .
C(2) C(9) 2.309(5) .
C(2) C(10) 2.285(5) .
C(2) C(11) 2.861(5) .
C(2) C(12) 3.100(5) .
C(2) C(17) 2.799(5) .
C(2) C(18) 3.569(5) .
C(2) C(22) 3.545(5) .
C(3) C(4) 2.450(5) .
C(3) C(6) 3.580(5) 56503
C(3) C(9) 2.307(5) .
C(3) C(17) 3.054(5) .
C(3) C(18) 3.530(5) .
C(4) C(6) 2.485(5) .
C(4) C(7) 3.130(5) .
C(4) C(8) 3.169(5) .
C(4) C(9) 2.565(5) .
C(4) C(9) 3.425(5) 56503
C(4) C(10) 3.515(5) 56503
C(5) C(7) 2.513(6) .
C(5) C(8) 3.154(6) .
C(5) C(9) 3.163(5) .
C(5) C(10) 2.494(5) .
C(6) O(1) 3.213(5) 46404
C(6) C(3) 3.580(5) 56503
C(6) C(8) 2.506(6) .
C(6) C(9) 3.120(5) .
C(6) C(10) 3.103(5) .
C(7) O(1) 3.242(4) 46404
C(7) C(9) 2.489(5) .
C(7) C(10) 3.137(5) .
C(8) C(10) 2.573(5) .
C(9) C(4) 3.425(5) 56503
C(10) C(4) 3.515(5) 56503
C(10) C(10) 3.583(5) 56503
C(10) C(18) 3.582(5) 66503
C(11) C(13) 2.415(6) .
C(11) C(14) 2.773(6) .
C(11) C(15) 2.403(5) .
C(11) C(17) 2.908(5) .
C(11) C(18) 3.202(5) .
C(12) C(14) 2.398(6) .
C(12) C(15) 2.757(6) .
C(12) C(16) 2.392(6) .
C(13) C(15) 2.386(7) .
C(13) C(16) 2.771(6) .
C(14) C(16) 2.383(6) .
C(16) C(17) 3.548(5) .
C(17) C(19) 2.402(5) .
C(17) C(20) 2.775(5) .
C(17) C(21) 2.403(5) .
C(18) C(10) 3.582(5) 66503
C(18) C(20) 2.404(6) .
C(18) C(21) 2.768(6) .
C(18) C(22) 2.407(6) .
C(19) C(21) 2.380(6) .
C(19) C(22) 2.762(6) .
C(20) C(22) 2.391(6) .
C(21) O(1) 3.177(5) 54502
C(22) O(1) 3.342(5) 54502
Br(1) H(6) 2.9251 .
Br(1) H(7) 3.5275 .
Br(1) H(12) 3.2697 55502
Br(1) H(13) 3.3843 56501
P(1) H(1) 3.0411 .
P(1) H(7) 2.9246 .
P(1) H(11) 2.8134 .
P(1) H(12) 2.8081 .
P(1) H(16) 2.9194 .
O(1) H(4) 2.5530 56504
O(1) H(5) 2.6183 56504
O(1) H(11) 2.9339 .
O(1) H(12) 2.7619 .
O(1) H(12) 2.8357 55502
O(1) H(13) 2.4877 55502
C(1) H(1) 3.1498 .
C(1) H(3) 3.5539 56503
C(1) H(6) 2.6640 .
C(1) H(7) 2.9053 .
C(1) H(15) 3.4252 66503
C(2) H(1) 2.0723 .
C(2) H(7) 2.6446 .
C(2) H(12) 3.5888 .
C(3) H(2) 2.5873 .
C(3) H(7) 3.3210 .
C(3) H(16) 3.0566 66503
C(4) H(1) 2.7317 .
C(4) H(3) 1.9804 .
C(4) H(4) 3.2608 .
C(4) H(16) 2.8481 66503
C(5) H(2) 1.9750 .
C(5) H(4) 1.9593 .
C(5) H(5) 3.2807 .
C(5) H(13) 3.2803 45404
C(5) H(16) 3.4984 66503
C(6) H(2) 3.2627 .
C(6) H(3) 1.9693 .
C(6) H(5) 1.9812 .
C(6) H(6) 3.2855 .
C(6) H(11) 3.1641 46404
C(6) H(12) 3.1630 56503
C(6) H(13) 3.5100 45404
C(7) H(1) 3.5732 56503
C(7) H(3) 3.2889 .
C(7) H(4) 1.9778 .
C(7) H(6) 1.9699 .
C(7) H(11) 3.3677 46404
C(7) H(15) 3.5630 66503
C(8) H(2) 3.4759 56503
C(8) H(4) 3.2744 .
C(8) H(5) 1.9626 .
C(8) H(15) 3.1524 66503
C(9) H(1) 3.2069 .
C(9) H(2) 3.3501 .
C(9) H(2) 3.3760 56503
C(9) H(5) 3.2679 .
C(9) H(6) 1.9856 .
C(9) H(15) 2.9920 66503
C(9) H(16) 3.5412 66503
C(10) H(1) 2.0676 .
C(10) H(2) 1.9623 .
C(10) H(3) 3.2717 .
C(10) H(6) 3.3643 .
C(10) H(15) 3.3350 66503
C(10) H(16) 2.8183 66503
C(11) H(2) 3.4919 66503
C(11) H(7) 2.0111 .
C(11) H(8) 3.2536 .
C(11) H(10) 3.2412 .
C(11) H(11) 2.0260 .
C(11) H(14) 3.1930 56501
C(11) H(16) 2.7851 .
C(12) H(1) 3.3029 66503
C(12) H(2) 3.2202 66503
C(12) H(8) 2.0352 .
C(12) H(9) 3.2390 .
C(12) H(11) 3.2328 .
C(12) H(14) 3.1087 56501
C(12) H(16) 3.2061 .
C(13) H(1) 3.3370 66503
C(13) H(2) 2.8462 66503
C(13) H(7) 2.0275 .
C(13) H(9) 2.0139 .
C(13) H(10) 3.2229 .
C(13) H(14) 2.9832 56501
C(13) H(15) 3.4113 56501
C(14) H(2) 2.7623 66503
C(14) H(7) 3.2369 .
C(14) H(8) 2.0216 .
C(14) H(10) 1.9945 .
C(14) H(11) 3.2186 .
C(14) H(14) 2.9290 56501
C(14) H(15) 3.2391 56501
C(15) H(2) 3.0495 66503
C(15) H(3) 3.3584 66503
C(15) H(8) 3.2249 .
C(15) H(9) 1.9947 .
C(15) H(11) 2.0124 .
C(15) H(14) 3.0222 56501
C(16) H(2) 3.4085 66503
C(16) H(4) 3.3963 56504
C(16) H(7) 3.2333 .
C(16) H(9) 3.2195 .
C(16) H(10) 2.0098 .
C(16) H(14) 3.1448 56501
C(16) H(16) 3.3496 .
C(17) H(1) 2.6909 .
C(17) H(10) 3.0018 64502
C(17) H(11) 3.4377 .
C(17) H(12) 2.0271 .
C(17) H(13) 3.2408 .
C(17) H(15) 3.2412 .
C(17) H(16) 2.0261 .
C(18) H(1) 2.9847 .
C(18) H(7) 3.3878 66503
C(18) H(10) 3.0096 64502
C(18) H(12) 3.2471 .
C(18) H(14) 3.2423 .
C(18) H(15) 2.0190 .
C(19) H(7) 3.1244 66503
C(19) H(10) 3.1120 64502
C(19) H(11) 3.4498 64502
C(19) H(13) 3.2182 .
C(19) H(14) 2.0131 .
C(19) H(16) 2.0239 .
C(20) H(3) 3.3029 55504
C(20) H(10) 3.2178 64502
C(20) H(12) 3.2269 .
C(20) H(13) 2.0004 .
C(20) H(15) 2.0103 .
C(20) H(16) 3.2421 .
C(21) H(3) 2.8650 55504
C(21) H(5) 3.5487 56503
C(21) H(10) 3.2081 64502
C(21) H(12) 2.0152 .
C(21) H(14) 2.0041 .
C(21) H(15) 3.2172 .
C(22) H(1) 3.1397 .
C(22) H(4) 3.1414 56503
C(22) H(10) 3.0855 64502
C(22) H(13) 2.0116 .
C(22) H(14) 3.2287 .
C(22) H(16) 3.2486 .
H(1) C(7) 3.5732 56503
H(1) C(12) 3.3029 66503
H(1) C(13) 3.3370 66503
H(2) C(8) 3.4759 56503
H(2) C(9) 3.3760 56503
H(2) C(11) 3.4919 66503
H(2) C(12) 3.2202 66503
H(2) C(13) 2.8462 66503
H(2) C(14) 2.7623 66503
H(2) C(15) 3.0495 66503
H(2) C(16) 3.4085 66503
H(3) C(1) 3.5539 56503
H(3) C(15) 3.3584 66503
H(3) C(20) 3.3029 45404
H(3) C(21) 2.8650 45404
H(4) O(1) 2.5530 46404
H(4) C(16) 3.3963 46404
H(4) C(22) 3.1414 56503
H(5) O(1) 2.6183 46404
H(5) C(21) 3.5487 56503
H(7) C(18) 3.3878 66503
H(7) C(19) 3.1244 66503
H(10) C(17) 3.0018 65502
H(10) C(18) 3.0096 65502
H(10) C(19) 3.1120 65502
H(10) C(20) 3.2178 65502
H(10) C(21) 3.2081 65502
H(10) C(22) 3.0855 65502
H(11) C(6) 3.1641 56504
H(11) C(7) 3.3677 56504
H(11) C(19) 3.4498 65502
H(12) Br(1) 3.2697 54502
H(12) O(1) 2.8357 54502
H(12) C(6) 3.1630 56503
H(13) Br(1) 3.3843 54501
H(13) O(1) 2.4877 54502
H(13) C(5) 3.2803 55504
H(13) C(6) 3.5100 55504
H(14) C(11) 3.1930 54501
H(14) C(12) 3.1087 54501
H(14) C(13) 2.9832 54501
H(14) C(14) 2.9290 54501
H(14) C(15) 3.0222 54501
H(14) C(16) 3.1448 54501
H(15) C(1) 3.4252 66503
H(15) C(7) 3.5630 66503
H(15) C(8) 3.1524 66503
H(15) C(9) 2.9920 66503
H(15) C(10) 3.3350 66503
H(15) C(13) 3.4113 54501
H(15) C(14) 3.2391 54501
H(16) C(3) 3.0566 66503
H(16) C(4) 2.8481 66503
H(16) C(5) 3.4984 66503
H(16) C(9) 3.5412 66503
H(16) C(10) 2.8183 66503
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
O(1) P(1) C(2) C(1) 53.5(4)
O(1) P(1) C(2) C(3) -126.7(3)
C(11) P(1) C(2) C(1) -71.4(4)
C(11) P(1) C(2) C(3) 108.4(3)
C(17) P(1) C(2) C(1) 176.3(3)
C(17) P(1) C(2) C(3) -4.0(3)
O(1) P(1) C(11) C(12) -132.3(3)
O(1) P(1) C(11) C(16) 46.4(3)
C(2) P(1) C(11) C(12) -6.3(3)
C(2) P(1) C(11) C(16) 172.4(3)
C(17) P(1) C(11) C(12) 102.8(3)
C(17) P(1) C(11) C(16) -78.5(3)
O(1) P(1) C(17) C(18) -150.5(3)
O(1) P(1) C(17) C(22) 34.7(3)
C(2) P(1) C(17) C(18) 85.5(3)
C(2) P(1) C(17) C(22) -89.4(3)
C(11) P(1) C(17) C(18) -25.3(3)
C(11) P(1) C(17) C(22) 159.8(2)
Br(1) C(1) C(2) P(1) -1.0(5)
Br(1) C(1) C(2) C(3) 179.2(3)
C(9) C(1) C(2) P(1) 178.5(3)
C(9) C(1) C(2) C(3) -1.3(4)
Br(1) C(1) C(9) C(8) 2.8(6)
Br(1) C(1) C(9) C(10) -179.6(3)
C(2) C(1) C(9) C(8) -176.7(4)
C(2) C(1) C(9) C(10) 0.9(4)
P(1) C(2) C(3) C(10) -178.7(3)
C(1) C(2) C(3) C(10) 1.1(4)
C(2) C(3) C(10) C(4) 177.2(4)
C(2) C(3) C(10) C(9) -0.6(4)
C(10) C(4) C(5) C(6) -0.9(7)
C(5) C(4) C(10) C(3) -174.6(4)
C(5) C(4) C(10) C(9) 2.8(7)
C(4) C(5) C(6) C(7) -2.3(7)
C(5) C(6) C(7) C(8) 1.4(7)
C(6) C(7) C(8) C(9) 2.3(7)
C(7) C(8) C(9) C(1) 174.1(4)
C(7) C(8) C(9) C(10) -3.0(7)
C(1) C(9) C(10) C(3) -0.2(4)
C(1) C(9) C(10) C(4) -177.9(4)
C(8) C(9) C(10) C(3) 177.4(4)
C(8) C(9) C(10) C(4) -0.3(6)
P(1) C(11) C(12) C(13) 178.4(3)
C(16) C(11) C(12) C(13) -0.2(5)
P(1) C(11) C(16) C(15) -178.9(3)
C(12) C(11) C(16) C(15) -0.1(4)
C(11) C(12) C(13) C(14) -0.1(5)
C(12) C(13) C(14) C(15) 0.8(6)
C(13) C(14) C(15) C(16) -1.2(7)
C(14) C(15) C(16) C(11) 0.8(6)
P(1) C(17) C(18) C(19) -174.1(3)
C(22) C(17) C(18) C(19) 0.7(5)
P(1) C(17) C(22) C(21) 173.2(3)
C(18) C(17) C(22) C(21) -1.9(5)
C(17) C(18) C(19) C(20) 0.5(6)
C(18) C(19) C(20) C(21) -0.4(6)
C(19) C(20) C(21) C(22) -0.8(6)
C(20) C(21) C(22) C(17) 1.9(6)
