#------------------------------------------------------------------------------
#$Date: 2016-03-21 15:08:08 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178738 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/49/4084984.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_4084984
loop_
_publ_author_name
'Hupf, Emanuel'
'Lork, Enno'
'Mebs, Stefan'
'Chęcińska, Lilianna'
'Beckmann, Jens'
_publ_section_title
;
 Probing Donor--Acceptor Interactions inperi-Substituted
 Diphenylphosphinoacenaphthyl--Element Dichlorides of Group 13 and 15
 Elements
;
_journal_issue                   24
_journal_name_full               Organometallics
_journal_page_first              7247
_journal_paper_doi               10.1021/om501036c
_journal_volume                  33
_journal_year                    2014
_chemical_formula_sum            'C24 H18 Bi Cl2 P'
_chemical_formula_weight         617.23
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 103.9550(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.3721(4)
_cell_length_b                   11.1934(4)
_cell_length_c                   18.9618(7)
_cell_measurement_reflns_used    9890
_cell_measurement_temperature    173
_cell_measurement_theta_max      32.44
_cell_measurement_theta_min      2.53
_cell_volume                     2136.47(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    Diamond
_computing_publication_material  WinGX
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Bruker Venture D8'
_diffrn_measurement_method       '2θ/ω 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  0.0655
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            120385
_diffrn_reflns_theta_full        32.60
_diffrn_reflns_theta_max         32.60
_diffrn_reflns_theta_min         2.53
_exptl_absorpt_coefficient_mu    8.585
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.4963
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Bruker, 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.919
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.440
_refine_diff_density_min         -1.107
_refine_diff_density_rms         0.198
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         7785
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0313
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0100P)²+8.3106P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0498
_refine_ls_wR_factor_ref         0.0551
_reflns_number_gt                6438
_reflns_number_total             7785
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om501036c_si_003.cif
_cod_data_source_block           9
_cod_depositor_comments
'Adding full bibliography for 4084974--4084984.cif.'
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4084984
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
Cl2 Cl 1.03917(8) 0.17374(7) 0.01435(4) 0.01558(14) Uani 1 1 d .
Cl1 Cl 0.65704(8) -0.09534(7) 0.08712(5) 0.02027(16) Uani 1 1 d .
Bi1 Bi 0.832445(11) 0.030677(10) 0.045562(6) 0.01160(3) Uani 1 1 d .
P1 P 0.77491(8) 0.21848(7) 0.12803(4) 0.01089(14) Uani 1 1 d .
C22 C 0.8735(3) 0.5395(3) 0.05621(16) 0.0148(6) Uani 1 1 d .
H22 H 0.9449 0.5706 0.0405 0.018 Uiso 1 1 calc R
C21 C 0.8741(3) 0.4202(3) 0.07697(16) 0.0135(6) Uani 1 1 d .
H21 H 0.9457 0.3714 0.0749 0.016 Uiso 1 1 calc R
C13 C 1.1669(3) -0.0278(3) 0.28736(17) 0.0165(6) Uani 1 1 d .
C10 C 0.9753(3) 0.0029(3) 0.15426(16) 0.0127(6) Uani 1 1 d .
C17 C 0.9458(3) 0.2844(3) 0.26070(17) 0.0159(6) Uani 1 1 d .
H17 H 0.8975 0.3551 0.2567 0.019 Uiso 1 1 calc R
C14 C 1.0859(3) 0.0747(3) 0.27322(16) 0.0132(6) Uani 1 1 d .
C30 C 0.6241(3) 0.1842(3) 0.15546(17) 0.0128(5) Uani 1 1 d .
C16 C 1.0489(3) 0.2649(3) 0.32345(18) 0.0178(6) Uani 1 1 d .
H16 H 1.0702 0.3228 0.3596 0.021 Uiso 1 1 calc R
C20 C 0.7669(3) 0.3740(3) 0.10091(16) 0.0124(5) Uani 1 1 d .
C1 C 1.2603(3) -0.0158(3) 0.36155(18) 0.0227(7) Uani 1 1 d .
H1A H 1.3521 -0.0181 0.3581 0.027 Uiso 1 1 calc R
H1B H 1.2459 -0.0794 0.3935 0.027 Uiso 1 1 calc R
C18 C 0.9140(3) 0.2012(3) 0.20469(16) 0.0138(6) Uani 1 1 d .
C15 C 1.1172(3) 0.1590(3) 0.33011(17) 0.0167(6) Uani 1 1 d .
C35 C 0.5056(3) 0.1832(3) 0.10228(18) 0.0176(6) Uani 1 1 d .
H35 H 0.5049 0.2047 0.0548 0.021 Uiso 1 1 calc R
C33 C 0.3905(4) 0.1147(3) 0.1898(2) 0.0271(8) Uani 1 1 d .
H33 H 0.3123 0.0902 0.2011 0.033 Uiso 1 1 calc R
C19 C 0.9875(3) 0.0930(3) 0.20835(16) 0.0120(5) Uani 1 1 d .
C2 C 1.2262(3) 0.1083(3) 0.39011(19) 0.0226(7) Uani 1 1 d .
H2A H 1.1960 0.0991 0.4344 0.027 Uiso 1 1 calc R
H2B H 1.3034 0.1602 0.3999 0.027 Uiso 1 1 calc R
C11 C 1.0550(3) -0.0970(3) 0.16811(18) 0.0179(6) Uani 1 1 d .
H11 H 1.0456 -0.1555 0.1324 0.021 Uiso 1 1 calc R
C23 C 0.7665(3) 0.6119(3) 0.05889(18) 0.0180(6) Uani 1 1 d .
H23 H 0.7658 0.6915 0.0447 0.022 Uiso 1 1 calc R
C24 C 0.6607(4) 0.5661(3) 0.0827(2) 0.0243(7) Uani 1 1 d .
H24 H 0.5892 0.6153 0.0845 0.029 Uiso 1 1 calc R
C25 C 0.6600(3) 0.4471(3) 0.1040(2) 0.0202(7) Uani 1 1 d .
H25 H 0.5887 0.4168 0.1201 0.024 Uiso 1 1 calc R
C32 C 0.5078(4) 0.1153(4) 0.2430(2) 0.0289(8) Uani 1 1 d .
H32 H 0.5080 0.0917 0.2900 0.035 Uiso 1 1 calc R
C12 C 1.1512(3) -0.1144(3) 0.23483(19) 0.0198(7) Uani 1 1 d .
H12 H 1.2027 -0.1833 0.2427 0.024 Uiso 1 1 calc R
C34 C 0.3885(3) 0.1503(3) 0.1199(2) 0.0226(7) Uani 1 1 d .
H34 H 0.3087 0.1521 0.0847 0.027 Uiso 1 1 calc R
C31 C 0.6256(3) 0.1509(3) 0.22644(19) 0.0204(7) Uani 1 1 d .
H31 H 0.7045 0.1525 0.2624 0.024 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
P P 0.1023 0.0942 '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'
Bi Bi -4.1077 10.2566 '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_3
Bi1 Cl2 Bi1 94.29(2) 3_755
C10 Bi1 Cl1 90.09(8) .
C10 Bi1 P1 76.80(8) .
Cl1 Bi1 P1 88.77(2) .
C10 Bi1 Cl2 84.60(8) .
Cl1 Bi1 Cl2 174.32(2) .
P1 Bi1 Cl2 88.06(2) .
C10 Bi1 Cl2 89.27(8) 3_755
Cl1 Bi1 Cl2 96.25(2) 3_755
P1 Bi1 Cl2 165.22(2) 3_755
Cl2 Bi1 Cl2 85.71(2) 3_755
C18 P1 C30 109.09(14) .
C18 P1 C20 107.84(14) .
C30 P1 C20 107.63(14) .
C18 P1 Bi1 97.76(10) .
C30 P1 Bi1 108.72(10) .
C20 P1 Bi1 124.78(10) .
C23 C22 C21 120.0(3) .
C22 C21 C20 119.8(3) .
C12 C13 C14 118.5(3) .
C12 C13 C1 132.6(3) .
C14 C13 C1 108.9(3) .
C11 C10 C19 119.5(3) .
C11 C10 Bi1 121.2(2) .
C19 C10 Bi1 119.2(2) .
C18 C17 C16 122.1(3) .
C13 C14 C19 123.8(3) .
C13 C14 C15 112.5(3) .
C19 C14 C15 123.7(3) .
C35 C30 C31 120.1(3) .
C35 C30 P1 118.0(2) .
C31 C30 P1 121.8(2) .
C15 C16 C17 118.7(3) .
C25 C20 C21 120.0(3) .
C25 C20 P1 122.4(2) .
C21 C20 P1 117.6(2) .
C13 C1 C2 104.7(3) .
C17 C18 C19 120.4(3) .
C17 C18 P1 122.9(2) .
C19 C18 P1 116.6(2) .
C16 C15 C14 119.3(3) .
C16 C15 C2 132.2(3) .
C14 C15 C2 108.5(3) .
C34 C35 C30 120.0(3) .
C34 C33 C32 120.5(3) .
C14 C19 C10 116.5(3) .
C14 C19 C18 115.6(3) .
C10 C19 C18 127.9(3) .
C15 C2 C1 105.3(3) .
C10 C11 C12 122.7(3) .
C24 C23 C22 120.1(3) .
C23 C24 C25 120.6(3) .
C20 C25 C24 119.4(3) .
C33 C32 C31 120.2(3) .
C13 C12 C11 119.0(3) .
C33 C34 C35 119.9(3) .
C32 C31 C30 119.2(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl2 Bi1 2.8503(7) .
Cl2 Bi1 3.0048(7) 3_755
Cl1 Bi1 2.5714(8) .
Bi1 C10 2.251(3) .
Bi1 P1 2.7696(8) .
Bi1 Cl2 3.0048(7) 3_755
P1 C18 1.794(3) .
P1 C30 1.805(3) .
P1 C20 1.811(3) .
C22 C23 1.385(5) .
C22 C21 1.391(4) .
C21 C20 1.398(4) .
C13 C12 1.371(5) .
C13 C14 1.409(4) .
C13 C1 1.510(4) .
C10 C11 1.378(4) .
C10 C19 1.422(4) .
C17 C18 1.391(4) .
C17 C16 1.412(4) .
C14 C19 1.411(4) .
C14 C15 1.411(4) .
C30 C35 1.389(4) .
C30 C31 1.393(4) .
C16 C15 1.370(5) .
C20 C25 1.391(4) .
C1 C2 1.562(5) .
C18 C19 1.424(4) .
C15 C2 1.508(5) .
C35 C34 1.384(5) .
C33 C34 1.379(5) .
C33 C32 1.380(6) .
C11 C12 1.423(5) .
C23 C24 1.381(5) .
C24 C25 1.393(5) .
C32 C31 1.391(5) .
