#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/11/57/4115750.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_4115750
loop_
_publ_author_name
'Yoshihiro Matano'
'Hazumi Nomura'
'Hitomi Suzuki'
'Motoo Shiro'
'Haruyuki Nakano'
_publ_contact_author_email       ' matano@kuchem.kyoto-u.ac.jp '
_publ_contact_author_fax         ' +81-75-753-4000 '
_publ_contact_author_name        ' Yoshihiro Matano'
_publ_contact_author_phone       ' +81-75-753-4045 '
_publ_section_title
;
 Synthesis, Structure, and Reactions of
 (Acylimino)triaryl-λ5-bismuthanes: First Comparative Study of the
 (Acylimino)pnictorane Series
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10954
_journal_page_last               10965
_journal_paper_doi               10.1021/ja003623l
_journal_volume                  123
_journal_year                    2001
_chemical_formula_moiety         'C20 H15 Cl3 N O P '
_chemical_formula_sum            'C20 H15 Cl3 N O P'
_chemical_formula_weight         422.68
_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                 94.90(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.469(3)
_cell_length_b                   19.063(4)
_cell_length_c                   10.976(4)
_cell_measurement_reflns_used    22
_cell_measurement_temperature    298.7
_cell_measurement_theta_max      14.6
_cell_measurement_theta_min      12.6
_cell_volume                     1974.0(10)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        'teXsan Ver. 1.10'
_computing_publication_material  'teXsan Ver. 1.10'
_computing_structure_refinement  'teXsan Ver. 1.10'
_computing_structure_solution    SIR92
_diffrn_measured_fraction_theta_full 1.0436
_diffrn_measured_fraction_theta_max 1.0436
_diffrn_measurement_device_type  'Rigaku AFC7S'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.021
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4800
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_standards_decay_%        5.64
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.554
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_description       prismatic
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.35
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4735
_refine_ls_R_factor_gt           0.0428
_refine_ls_shift/su_max          0.0003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.05100(Max(Fo²,0) + 2Fc²)/3)²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1321
_reflns_number_gt                2884
_reflns_number_total             4735
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ja003623l_2.cif
_cod_data_source_block           Ph3P_NCOCCl3
_cod_original_cell_volume        1973(1)
_cod_original_formula_sum        'C20 H15 Cl3 N O P '
_cod_database_code               4115750
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,1/2+y,1/2-z
-x,-y,-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_calc_flag
Cl(1) Cl -0.43679(9) 0.22753(5) 0.16242(10) 0.0822(3) Uani 1.00 d
Cl(2) Cl -0.41438(9) 0.13712(6) 0.37374(8) 0.0787(3) Uani 1.00 d
Cl(3) Cl -0.47651(9) 0.07958(5) 0.13282(9) 0.0807(3) Uani 1.00 d
P P 0.02936(6) 0.18463(3) 0.24884(5) 0.0326(2) Uani 1.00 d
O O -0.1776(2) 0.07258(9) 0.2033(2) 0.0471(5) Uani 1.00 d
N N -0.1417(2) 0.19175(10) 0.2316(2) 0.0391(6) Uani 1.00 d
C(1) C -0.2172(3) 0.1330(1) 0.2141(2) 0.0362(6) Uani 1.00 d
C(2) C -0.3799(3) 0.1449(1) 0.2165(3) 0.0479(8) Uani 1.00 d
C(3) C 0.1102(2) 0.1521(1) 0.1175(2) 0.0340(6) Uani 1.00 d
C(4) C 0.1719(3) 0.1986(1) 0.0400(2) 0.0463(7) Uani 1.00 d
C(5) C 0.2288(3) 0.1742(2) -0.0641(2) 0.0564(9) Uani 1.00 d
C(6) C 0.2258(3) 0.1036(2) -0.0901(2) 0.0558(9) Uani 1.00 d
C(7) C 0.1660(3) 0.0569(1) -0.0136(3) 0.0506(8) Uani 1.00 d
C(8) C 0.1072(3) 0.0808(1) 0.0896(2) 0.0412(7) Uani 1.00 d
C(9) C 0.0936(3) 0.2724(1) 0.2756(2) 0.0381(6) Uani 1.00 d
C(10) C 0.0154(3) 0.3287(1) 0.2241(3) 0.0504(8) Uani 1.00 d
C(11) C 0.0689(4) 0.3958(1) 0.2368(3) 0.066(1) Uani 1.00 d
C(12) C 0.1979(4) 0.4072(2) 0.3006(4) 0.075(1) Uani 1.00 d
C(13) C 0.2754(4) 0.3529(2) 0.3513(3) 0.077(1) Uani 1.00 d
C(14) C 0.2240(3) 0.2845(2) 0.3389(3) 0.0578(9) Uani 1.00 d
C(15) C 0.0884(3) 0.1310(1) 0.3782(2) 0.0378(6) Uani 1.00 d
C(16) C 0.0053(3) 0.1274(2) 0.4766(2) 0.0522(8) Uani 1.00 d
C(17) C 0.0489(4) 0.0859(2) 0.5758(3) 0.068(1) Uani 1.00 d
C(18) C 0.1730(4) 0.0480(2) 0.5786(3) 0.069(1) Uani 1.00 d
C(19) C 0.2549(4) 0.0522(2) 0.4829(3) 0.069(1) Uani 1.00 d
C(20) C 0.2140(3) 0.0932(2) 0.3820(2) 0.0523(8) Uani 1.00 d
H(1) H 0.1776 0.2477 0.0601 0.0552 Uiso 1.00 calc
H(2) H 0.2679 0.2065 -0.1197 0.0695 Uiso 1.00 calc
H(3) H 0.2680 0.0874 -0.1615 0.0660 Uiso 1.00 calc
H(4) H 0.1647 0.0078 -0.0327 0.0620 Uiso 1.00 calc
H(5) H 0.0622 0.0485 0.1425 0.0507 Uiso 1.00 calc
H(6) H -0.0750 0.3206 0.1815 0.0607 Uiso 1.00 calc
H(7) H 0.0143 0.4345 0.2012 0.0785 Uiso 1.00 calc
H(8) H 0.2330 0.4550 0.3068 0.0867 Uiso 1.00 calc
H(9) H 0.3649 0.3620 0.3976 0.0929 Uiso 1.00 calc
H(10) H 0.2792 0.2458 0.3741 0.0714 Uiso 1.00 calc
H(11) H -0.0815 0.1539 0.4740 0.0626 Uiso 1.00 calc
H(12) H -0.0076 0.0831 0.6447 0.0847 Uiso 1.00 calc
H(13) H 0.2033 0.0179 0.6476 0.0822 Uiso 1.00 calc
H(14) H 0.3452 0.0272 0.4857 0.0839 Uiso 1.00 calc
H(15) H 0.2713 0.0965 0.3142 0.0639 Uiso 1.00 calc
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 6.1.1.1)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
Cl Cl 0.148 0.159
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
N N 0.006 0.003
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
O O 0.011 0.006
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
P P 0.102 0.094
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N P C(3) 115.1(1) 1_555 1_555 yes
N P C(9) 105.2(1) 1_555 1_555 yes
N P C(15) 112.3(1) 1_555 1_555 yes
C(3) P C(9) 106.9(1) 1_555 1_555 yes
C(3) P C(15) 108.1(1) 1_555 1_555 yes
C(9) P C(15) 108.8(1) 1_555 1_555 yes
P N C(1) 117.7(2) 1_555 1_555 yes
O C(1) N 129.9(2) 1_555 1_555 yes
O C(1) C(2) 116.8(2) 1_555 1_555 yes
N C(1) C(2) 113.2(2) 1_555 1_555 yes
Cl(1) C(2) Cl(2) 109.0(1) 1_555 1_555 yes
Cl(1) C(2) Cl(3) 109.2(2) 1_555 1_555 yes
Cl(1) C(2) C(1) 113.6(2) 1_555 1_555 yes
Cl(2) C(2) Cl(3) 108.4(1) 1_555 1_555 yes
Cl(2) C(2) C(1) 105.4(2) 1_555 1_555 yes
Cl(3) C(2) C(1) 111.0(2) 1_555 1_555 yes
P C(3) C(4) 119.9(2) 1_555 1_555 yes
P C(3) C(8) 120.7(2) 1_555 1_555 yes
C(4) C(3) C(8) 119.3(2) 1_555 1_555 yes
C(3) C(4) C(5) 120.2(2) 1_555 1_555 yes
C(3) C(4) H(1) 119.9 1_555 1_555 no
C(5) C(4) H(1) 119.9 1_555 1_555 no
C(4) C(5) C(6) 119.9(3) 1_555 1_555 yes
C(4) C(5) H(2) 120.3 1_555 1_555 no
C(6) C(5) H(2) 119.8 1_555 1_555 no
C(5) C(6) C(7) 120.5(2) 1_555 1_555 yes
C(5) C(6) H(3) 118.8 1_555 1_555 no
C(7) C(6) H(3) 120.8 1_555 1_555 no
C(6) C(7) C(8) 120.2(2) 1_555 1_555 yes
C(6) C(7) H(4) 119.7 1_555 1_555 no
C(8) C(7) H(4) 120.2 1_555 1_555 no
C(3) C(8) C(7) 120.0(2) 1_555 1_555 yes
C(3) C(8) H(5) 119.3 1_555 1_555 no
C(7) C(8) H(5) 120.7 1_555 1_555 no
P C(9) C(10) 119.3(2) 1_555 1_555 yes
P C(9) C(14) 120.9(2) 1_555 1_555 yes
C(10) C(9) C(14) 119.6(2) 1_555 1_555 yes
C(9) C(10) C(11) 119.7(3) 1_555 1_555 yes
C(9) C(10) H(6) 119.8 1_555 1_555 no
C(11) C(10) H(6) 120.5 1_555 1_555 no
C(10) C(11) C(12) 120.2(3) 1_555 1_555 yes
C(10) C(11) H(7) 119.3 1_555 1_555 no
C(12) C(11) H(7) 120.6 1_555 1_555 no
C(11) C(12) C(13) 120.9(3) 1_555 1_555 yes
C(11) C(12) H(8) 118.0 1_555 1_555 no
C(13) C(12) H(8) 121.1 1_555 1_555 no
C(12) C(13) C(14) 120.0(3) 1_555 1_555 yes
C(12) C(13) H(9) 119.7 1_555 1_555 no
C(14) C(13) H(9) 120.3 1_555 1_555 no
C(9) C(14) C(13) 119.7(3) 1_555 1_555 yes
C(9) C(14) H(10) 120.2 1_555 1_555 no
C(13) C(14) H(10) 120.1 1_555 1_555 no
P C(15) C(16) 118.8(2) 1_555 1_555 yes
P C(15) C(20) 121.8(2) 1_555 1_555 yes
C(16) C(15) C(20) 119.4(2) 1_555 1_555 yes
C(15) C(16) C(17) 119.3(3) 1_555 1_555 yes
C(15) C(16) H(11) 119.3 1_555 1_555 no
C(17) C(16) H(11) 121.5 1_555 1_555 no
C(16) C(17) C(18) 121.0(3) 1_555 1_555 yes
C(16) C(17) H(12) 120.1 1_555 1_555 no
C(18) C(17) H(12) 118.9 1_555 1_555 no
C(17) C(18) C(19) 119.6(3) 1_555 1_555 yes
C(17) C(18) H(13) 121.3 1_555 1_555 no
C(19) C(18) H(13) 119.1 1_555 1_555 no
C(18) C(19) C(20) 120.8(3) 1_555 1_555 yes
C(18) C(19) H(14) 120.2 1_555 1_555 no
C(20) C(19) H(14) 119.0 1_555 1_555 no
C(15) C(20) C(19) 119.9(3) 1_555 1_555 yes
C(15) C(20) H(15) 118.8 1_555 1_555 no
C(19) C(20) H(15) 121.4 1_555 1_555 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl(1) C(2) 1.751(3) yes
Cl(2) C(2) 1.790(3) yes
Cl(3) C(2) 1.757(3) yes
P N 1.620(2) yes
P C(3) 1.800(2) yes
P C(9) 1.796(2) yes
P C(15) 1.799(2) yes
O C(1) 1.220(3) yes
N C(1) 1.333(3) yes
C(1) C(2) 1.560(4) yes
C(3) C(4) 1.392(3) yes
C(3) C(8) 1.392(3) yes
C(4) C(5) 1.385(4) yes
C(4) H(1) 0.962 no
C(5) C(6) 1.375(4) yes
C(5) H(2) 0.964 no
C(6) C(7) 1.378(4) yes
C(6) H(3) 0.960 no
C(7) C(8) 1.382(4) yes
C(7) H(4) 0.959 no
C(8) H(5) 0.969 no
C(9) C(10) 1.395(4) yes
C(9) C(14) 1.383(4) yes
C(10) C(11) 1.379(4) yes
C(10) H(6) 0.953 no
C(11) C(12) 1.372(5) yes
C(11) H(7) 0.964 no
C(12) C(13) 1.361(5) yes
C(12) H(8) 0.969 no
C(13) C(14) 1.393(4) yes
C(13) H(9) 0.966 no
C(14) H(10) 0.966 no
C(15) C(16) 1.392(3) yes
C(15) C(20) 1.389(4) yes
C(16) C(17) 1.381(4) yes
C(16) H(11) 0.962 no
C(17) C(18) 1.377(5) yes
C(17) H(12) 0.964 no
C(18) C(19) 1.360(5) yes
C(18) H(13) 0.975 no
C(19) C(20) 1.383(4) yes
C(19) H(14) 0.977 no
C(20) H(15) 0.960 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
Cl(1) C(16) 3.452(3) 4_454
O C(7) 3.237(3) 3_555
O C(18) 3.317(4) 3_556
O C(6) 3.596(4) 3_555
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
_geom_torsion_publ_flag
Cl(1) C(2) C(1) O -152.1(2) 1_555 1_555 1_555 1_555 yes
Cl(1) C(2) C(1) N 31.4(3) 1_555 1_555 1_555 1_555 yes
Cl(2) C(2) C(1) O 88.6(2) 1_555 1_555 1_555 1_555 yes
Cl(2) C(2) C(1) N -87.9(2) 1_555 1_555 1_555 1_555 yes
Cl(3) C(2) C(1) O -28.5(3) 1_555 1_555 1_555 1_555 yes
Cl(3) C(2) C(1) N 155.0(2) 1_555 1_555 1_555 1_555 yes
P N C(1) O -3.7(4) 1_555 1_555 1_555 1_555 yes
P N C(1) C(2) 172.1(2) 1_555 1_555 1_555 1_555 yes
P C(3) C(4) C(5) -177.2(2) 1_555 1_555 1_555 1_555 yes
P C(3) C(8) C(7) 178.0(2) 1_555 1_555 1_555 1_555 yes
P C(9) C(10) C(11) -175.3(2) 1_555 1_555 1_555 1_555 yes
P C(9) C(14) C(13) 175.8(3) 1_555 1_555 1_555 1_555 yes
P C(15) C(16) C(17) 179.4(2) 1_555 1_555 1_555 1_555 yes
P C(15) C(20) C(19) -179.6(2) 1_555 1_555 1_555 1_555 yes
N P C(3) C(4) 99.6(2) 1_555 1_555 1_555 1_555 yes
N P C(3) C(8) -78.0(2) 1_555 1_555 1_555 1_555 yes
N P C(9) C(10) -29.7(2) 1_555 1_555 1_555 1_555 yes
N P C(9) C(14) 155.0(2) 1_555 1_555 1_555 1_555 yes
N P C(15) C(16) -28.1(2) 1_555 1_555 1_555 1_555 yes
N P C(15) C(20) 151.6(2) 1_555 1_555 1_555 1_555 yes
C(1) N P C(3) 64.7(2) 1_555 1_555 1_555 1_555 yes
C(1) N P C(9) -177.8(2) 1_555 1_555 1_555 1_555 yes
C(1) N P C(15) -59.7(2) 1_555 1_555 1_555 1_555 yes
C(3) P C(9) C(10) 93.1(2) 1_555 1_555 1_555 1_555 yes
C(3) P C(9) C(14) -82.1(2) 1_555 1_555 1_555 1_555 yes
C(3) P C(15) C(16) -156.3(2) 1_555 1_555 1_555 1_555 yes
C(3) P C(15) C(20) 23.5(2) 1_555 1_555 1_555 1_555 yes
C(3) C(4) C(5) C(6) -0.8(5) 1_555 1_555 1_555 1_555 yes
C(3) C(8) C(7) C(6) -0.9(4) 1_555 1_555 1_555 1_555 yes
C(4) C(3) P C(9) -16.9(2) 1_555 1_555 1_555 1_555 yes
C(4) C(3) P C(15) -133.9(2) 1_555 1_555 1_555 1_555 yes
C(4) C(3) C(8) C(7) 0.4(4) 1_555 1_555 1_555 1_555 yes
C(4) C(5) C(6) C(7) 0.3(5) 1_555 1_555 1_555 1_555 yes
C(5) C(4) C(3) C(8) 0.4(4) 1_555 1_555 1_555 1_555 yes
C(5) C(6) C(7) C(8) 0.6(4) 1_555 1_555 1_555 1_555 yes
C(8) C(3) P C(9) 165.6(2) 1_555 1_555 1_555 1_555 yes
C(8) C(3) P C(15) 48.6(2) 1_555 1_555 1_555 1_555 yes
C(9) P C(15) C(16) 87.9(2) 1_555 1_555 1_555 1_555 yes
C(9) P C(15) C(20) -92.3(2) 1_555 1_555 1_555 1_555 yes
C(9) C(10) C(11) C(12) -0.5(5) 1_555 1_555 1_555 1_555 yes
C(9) C(14) C(13) C(12) -0.5(5) 1_555 1_555 1_555 1_555 yes
C(10) C(9) P C(15) -150.3(2) 1_555 1_555 1_555 1_555 yes
C(10) C(9) C(14) C(13) 0.5(4) 1_555 1_555 1_555 1_555 yes
C(10) C(11) C(12) C(13) 0.4(6) 1_555 1_555 1_555 1_555 yes
C(11) C(10) C(9) C(14) 0.0(4) 1_555 1_555 1_555 1_555 yes
C(11) C(12) C(13) C(14) 0.0(6) 1_555 1_555 1_555 1_555 yes
C(14) C(9) P C(15) 34.4(2) 1_555 1_555 1_555 1_555 yes
C(15) C(16) C(17) C(18) -0.1(4) 1_555 1_555 1_555 1_555 yes
C(15) C(20) C(19) C(18) 0.5(5) 1_555 1_555 1_555 1_555 yes
C(16) C(15) C(20) C(19) 0.2(4) 1_555 1_555 1_555 1_555 yes
C(16) C(17) C(18) C(19) 0.9(5) 1_555 1_555 1_555 1_555 yes
C(17) C(16) C(15) C(20) -0.4(4) 1_555 1_555 1_555 1_555 yes
C(17) C(18) C(19) C(20) -1.1(5) 1_555 1_555 1_555 1_555 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10458578
