#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/54/2015410.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2015410
loop_
_publ_author_name
'Levason, William'
'Reid, Gillian'
'Webster, Michael'
_publ_section_title
;
 1,2-Bis(diphenylphosphino)benzene and two related mono-methiodides,
 [o-C₆H₄(PR₂)(PR₂Me)]I (R = Ph or
 Me)
;
_journal_coeditor_code           FA3012
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o438
_journal_page_last               o440
_journal_paper_doi               10.1107/S0108270106015915
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C30 H24 P2'
_chemical_formula_moiety         'C30 H24 P2'
_chemical_formula_sum            'C30 H24 P2'
_chemical_formula_weight         446.43
_chemical_name_common            o-phenylenebis(diphenylphosphine)
_chemical_name_systematic
;
1,2-bis(diphenylphosphino)benzene
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL-97 + hand edit'
_cell_angle_alpha                109.846(5)
_cell_angle_beta                 99.918(5)
_cell_angle_gamma                98.330(15)
_cell_formula_units_Z            2
_cell_length_a                   8.1930(15)
_cell_length_b                   12.442(2)
_cell_length_c                   12.584(3)
_cell_measurement_reflns_used    19324
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1159.6(4)
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_collection
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_data_reduction        'COLLECT and DENZO'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Nonius rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1317
_diffrn_reflns_av_sigmaI/netI    0.1802
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15781
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.95
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.535
_refine_diff_density_min         -0.327
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         5122
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.925
_refine_ls_R_factor_all          0.1566
_refine_ls_R_factor_gt           0.0563
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0398P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1319
_reflns_number_gt                2565
_reflns_number_total             5122
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fa3012.cif
_cod_data_source_block           I
_cod_database_code               2015410
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
P P1 0.09646(10) 0.23706(7) 0.30948(7) 0.0236(2) Uani d . 1
P P2 -0.13684(10) -0.00554(7) 0.13258(7) 0.0268(2) Uani d . 1
C C1 -0.1175(3) 0.1934(2) 0.3309(2) 0.0202(7) Uani d . 1
C C2 -0.2208(4) 0.0838(2) 0.2523(2) 0.0221(7) Uani d . 1
C C3 -0.3839(4) 0.0516(3) 0.2645(3) 0.0261(7) Uani d . 1
H H3 -0.4527 -0.0226 0.2139 0.0307(18) Uiso calc R 1
C C4 -0.4490(4) 0.1255(3) 0.3493(3) 0.0270(8) Uani d . 1
H H4 -0.5623 0.1027 0.3543 0.0307(18) Uiso calc R 1
C C5 -0.3474(4) 0.2330(3) 0.4268(2) 0.0243(7) Uani d . 1
H H5 -0.3907 0.2844 0.4846 0.0307(18) Uiso calc R 1
C C6 -0.1820(4) 0.2634(2) 0.4181(2) 0.0230(7) Uani d . 1
H H6 -0.1105 0.3345 0.4736 0.0307(18) Uiso calc R 1
C C7 0.2186(3) 0.3115(3) 0.4613(2) 0.0224(7) Uani d . 1
C C8 0.2469(4) 0.2409(3) 0.5256(3) 0.0272(7) Uani d . 1
H H8 0.1923 0.1602 0.4930 0.0307(18) Uiso calc R 1
C C9 0.3531(4) 0.2868(3) 0.6358(3) 0.0327(8) Uani d . 1
H H9 0.3706 0.2377 0.6785 0.0307(18) Uiso calc R 1
C C10 0.4340(4) 0.4038(3) 0.6841(3) 0.0329(8) Uani d . 1
H H10 0.5086 0.4350 0.7593 0.0307(18) Uiso calc R 1
C C11 0.4059(4) 0.4748(3) 0.6227(3) 0.0317(8) Uani d . 1
H H11 0.4596 0.5556 0.6565 0.0307(18) Uiso calc R 1
C C12 0.2997(4) 0.4293(3) 0.5117(3) 0.0266(7) Uani d . 1
H H12 0.2823 0.4791 0.4699 0.0307(18) Uiso calc R 1
C C13 0.0741(3) 0.3568(2) 0.2578(2) 0.0217(7) Uani d . 1
C C14 0.1414(4) 0.3541(3) 0.1622(3) 0.0299(8) Uani d . 1
H H14 0.1947 0.2924 0.1283 0.0307(18) Uiso calc R 1
C C15 0.1312(4) 0.4405(3) 0.1164(3) 0.0346(8) Uani d . 1
H H15 0.1755 0.4366 0.0506 0.0307(18) Uiso calc R 1
C C16 0.0572(4) 0.5320(3) 0.1659(3) 0.0312(8) Uani d . 1
H H16 0.0528 0.5918 0.1352 0.0307(18) Uiso calc R 1
C C17 -0.0109(4) 0.5367(3) 0.2603(3) 0.0300(8) Uani d . 1
H H17 -0.0623 0.5995 0.2945 0.0307(18) Uiso calc R 1
C C18 -0.0034(4) 0.4487(3) 0.3048(3) 0.0274(8) Uani d . 1
H H18 -0.0522 0.4514 0.3686 0.0307(18) Uiso calc R 1
C C19 -0.3111(4) -0.1371(3) 0.0608(3) 0.0275(8) Uani d . 1
C C20 -0.3281(4) -0.2339(3) 0.0934(3) 0.0298(8) Uani d . 1
H H20 -0.2469 -0.2338 0.1572 0.0307(18) Uiso calc R 1
C C21 -0.4619(4) -0.3301(3) 0.0343(3) 0.0329(8) Uani d . 1
H H21 -0.4731 -0.3946 0.0587 0.0307(18) Uiso calc R 1
C C22 -0.5789(4) -0.3324(3) -0.0599(3) 0.0368(9) Uani d . 1
H H22 -0.6709 -0.3981 -0.1002 0.0307(18) Uiso calc R 1
C C23 -0.5618(4) -0.2388(3) -0.0956(3) 0.0397(9) Uani d . 1
H H23 -0.6416 -0.2406 -0.1610 0.0307(18) Uiso calc R 1
C C24 -0.4291(4) -0.1425(3) -0.0364(3) 0.0360(9) Uani d . 1
H H24 -0.4178 -0.0790 -0.0622 0.0307(18) Uiso calc R 1
C C25 0.0162(4) -0.0645(2) 0.2096(3) 0.0243(7) Uani d . 1
C C26 0.0205(4) -0.0640(3) 0.3206(3) 0.0293(8) Uani d . 1
H H26 -0.0579 -0.0305 0.3619 0.0307(18) Uiso calc R 1
C C27 0.1393(4) -0.1126(3) 0.3720(3) 0.0333(8) Uani d . 1
H H27 0.1436 -0.1102 0.4487 0.0307(18) Uiso calc R 1
C C28 0.2503(4) -0.1641(3) 0.3110(3) 0.0335(8) Uani d . 1
H H28 0.3314 -0.1970 0.3459 0.0307(18) Uiso calc R 1
C C29 0.2443(4) -0.1679(3) 0.1997(3) 0.0336(8) Uani d . 1
H H29 0.3192 -0.2053 0.1574 0.0307(18) Uiso calc R 1
C C30 0.1294(4) -0.1173(2) 0.1487(3) 0.0279(8) Uani d . 1
H H30 0.1278 -0.1185 0.0727 0.0307(18) Uiso calc R 1
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C13 P1 C7 104.17(13) y
C13 P1 C1 102.65(13) y
C7 P1 C1 100.67(13) y
C25 P2 C19 99.70(14) y
C25 P2 C2 101.79(13) y
C19 P2 C2 101.67(13) y
C6 C1 C2 118.9(3) ?
C6 C1 P1 123.2(2) ?
C2 C1 P1 117.8(2) y
C3 C2 C1 118.6(3) ?
C3 C2 P2 122.9(2) ?
C1 C2 P2 118.4(2) y
C2 C3 C4 121.6(3) ?
C2 C3 H3 119.2 ?
C4 C3 H3 119.2 ?
C3 C4 C5 119.8(3) ?
C3 C4 H4 120.1 ?
C5 C4 H4 120.1 ?
C6 C5 C4 118.8(3) ?
C6 C5 H5 120.6 ?
C4 C5 H5 120.6 ?
C5 C6 C1 122.1(3) ?
C5 C6 H6 118.9 ?
C1 C6 H6 118.9 ?
C12 C7 C8 118.2(3) ?
C12 C7 P1 124.7(2) ?
C8 C7 P1 116.8(2) ?
C9 C8 C7 120.9(3) ?
C9 C8 H8 119.6 ?
C7 C8 H8 119.6 ?
C10 C9 C8 120.2(3) ?
C10 C9 H9 119.9 ?
C8 C9 H9 119.9 ?
C11 C10 C9 119.6(3) ?
C11 C10 H10 120.2 ?
C9 C10 H10 120.2 ?
C10 C11 C12 120.5(3) ?
C10 C11 H11 119.7 ?
C12 C11 H11 119.7 ?
C11 C12 C7 120.6(3) ?
C11 C12 H12 119.7 ?
C7 C12 H12 119.7 ?
C18 C13 C14 117.8(3) ?
C18 C13 P1 126.0(2) ?
C14 C13 P1 116.3(2) ?
C15 C14 C13 120.8(3) ?
C15 C14 H14 119.6 ?
C13 C14 H14 119.6 ?
C16 C15 C14 120.4(3) ?
C16 C15 H15 119.8 ?
C14 C15 H15 119.8 ?
C15 C16 C17 120.0(3) ?
C15 C16 H16 120.0 ?
C17 C16 H16 120.0 ?
C16 C17 C18 119.5(3) ?
C16 C17 H17 120.2 ?
C18 C17 H17 120.2 ?
C17 C18 C13 121.5(3) ?
C17 C18 H18 119.3 ?
C13 C18 H18 119.3 ?
C20 C19 C24 117.8(3) ?
C20 C19 P2 124.4(2) ?
C24 C19 P2 117.7(3) ?
C21 C20 C19 121.0(3) ?
C21 C20 H20 119.5 ?
C19 C20 H20 119.5 ?
C22 C21 C20 120.1(3) ?
C22 C21 H21 120.0 ?
C20 C21 H21 120.0 ?
C21 C22 C23 119.8(3) ?
C21 C22 H22 120.1 ?
C23 C22 H22 120.1 ?
C22 C23 C24 120.2(3) ?
C22 C23 H23 119.9 ?
C24 C23 H23 119.9 ?
C23 C24 C19 121.0(3) ?
C23 C24 H24 119.5 ?
C19 C24 H24 119.5 ?
C26 C25 C30 119.0(3) ?
C26 C25 P2 124.2(2) ?
C30 C25 P2 116.7(2) ?
C25 C26 C27 120.5(3) ?
C25 C26 H26 119.8 ?
C27 C26 H26 119.8 ?
C28 C27 C26 119.8(3) ?
C28 C27 H27 120.1 ?
C26 C27 H27 120.1 ?
C29 C28 C27 120.3(3) ?
C29 C28 H28 119.9 ?
C27 C28 H28 119.9 ?
C28 C29 C30 120.4(3) ?
C28 C29 H29 119.8 ?
C30 C29 H29 119.8 ?
C29 C30 C25 120.0(3) ?
C29 C30 H30 120.0 ?
C25 C30 H30 120.0 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
P1 C1 1.851(3) y
P1 C7 1.839(3) y
P1 C13 1.836(3) y
P2 C2 1.849(3) y
P2 C19 1.846(3) y
P2 C25 1.838(3) y
C1 C6 1.388(4) ?
C1 C2 1.420(4) y
C2 C3 1.388(4) ?
C3 C4 1.393(4) ?
C3 H3 0.9500 ?
C4 C5 1.394(4) ?
C4 H4 0.9500 ?
C5 C6 1.387(4) ?
C5 H5 0.9500 ?
C6 H6 0.9500 ?
C7 C12 1.390(4) ?
C7 C8 1.399(4) ?
C8 C9 1.382(4) ?
C8 H8 0.9500 ?
C9 C10 1.382(4) ?
C9 H9 0.9500 ?
C10 C11 1.375(4) ?
C10 H10 0.9500 ?
C11 C12 1.389(4) ?
C11 H11 0.9500 ?
C12 H12 0.9500 ?
C13 C18 1.394(4) ?
C13 C14 1.398(4) ?
C14 C15 1.387(4) ?
C14 H14 0.9500 ?
C15 C16 1.378(4) ?
C15 H15 0.9500 ?
C16 C17 1.385(4) ?
C16 H16 0.9500 ?
C17 C18 1.393(4) ?
C17 H17 0.9500 ?
C18 H18 0.9500 ?
C19 C20 1.394(4) ?
C19 C24 1.398(4) ?
C20 C21 1.387(4) ?
C20 H20 0.9500 ?
C21 C22 1.380(4) ?
C21 H21 0.9500 ?
C22 C23 1.380(4) ?
C22 H22 0.9500 ?
C23 C24 1.382(4) ?
C23 H23 0.9500 ?
C24 H24 0.9500 ?
C25 C26 1.390(4) ?
C25 C30 1.399(4) ?
C26 C27 1.396(4) ?
C26 H26 0.9500 ?
C27 C28 1.380(4) ?
C27 H27 0.9500 ?
C28 C29 1.377(4) ?
C28 H28 0.9500 ?
C29 C30 1.389(4) ?
C29 H29 0.9500 ?
C30 H30 0.9500 ?
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
C13 P1 C1 C6 -69.3(3)
C7 P1 C1 C6 38.0(3)
C13 P1 C1 C2 109.4(2)
C7 P1 C1 C2 -143.3(2)
C6 C1 C2 C3 1.0(4)
P1 C1 C2 C3 -177.7(2)
C6 C1 C2 P2 177.3(2)
P1 C1 C2 P2 -1.4(3)
C25 P2 C2 C3 -108.3(3)
C19 P2 C2 C3 -5.7(3)
C25 P2 C2 C1 75.6(2)
C19 P2 C2 C1 178.2(2)
C1 C2 C3 C4 1.9(4)
P2 C2 C3 C4 -174.2(2)
C2 C3 C4 C5 -2.2(5)
C3 C4 C5 C6 -0.5(4)
C4 C5 C6 C1 3.6(4)
C2 C1 C6 C5 -3.8(4)
P1 C1 C6 C5 174.8(2)
C13 P1 C7 C12 -11.1(3)
C1 P1 C7 C12 -117.2(3)
C13 P1 C7 C8 176.5(2)
C1 P1 C7 C8 70.4(2)
C12 C7 C8 C9 -0.3(4)
P1 C7 C8 C9 172.6(2)
C7 C8 C9 C10 -0.3(4)
C8 C9 C10 C11 1.1(5)
C9 C10 C11 C12 -1.3(5)
C10 C11 C12 C7 0.6(5)
C8 C7 C12 C11 0.2(4)
P1 C7 C12 C11 -172.2(2)
C7 P1 C13 C18 -59.5(3)
C1 P1 C13 C18 45.1(3)
C7 P1 C13 C14 120.7(2)
C1 P1 C13 C14 -134.7(2)
C18 C13 C14 C15 0.2(4)
P1 C13 C14 C15 -180.0(2)
C13 C14 C15 C16 1.2(4)
C14 C15 C16 C17 -1.4(4)
C15 C16 C17 C18 0.2(4)
C16 C17 C18 C13 1.3(4)
C14 C13 C18 C17 -1.4(4)
P1 C13 C18 C17 178.8(2)
C25 P2 C19 C20 17.6(3)
C2 P2 C19 C20 -86.7(3)
C25 P2 C19 C24 -159.1(2)
C2 P2 C19 C24 96.6(3)
C24 C19 C20 C21 -2.7(5)
P2 C19 C20 C21 -179.3(2)
C19 C20 C21 C22 1.4(5)
C20 C21 C22 C23 0.4(5)
C21 C22 C23 C24 -0.7(5)
C22 C23 C24 C19 -0.7(5)
C20 C19 C24 C23 2.3(5)
P2 C19 C24 C23 179.2(2)
C19 P2 C25 C26 -88.4(3)
C2 P2 C25 C26 15.8(3)
C19 P2 C25 C30 88.7(2)
C2 P2 C25 C30 -167.1(2)
C30 C25 C26 C27 1.8(4)
P2 C25 C26 C27 178.8(2)
C25 C26 C27 C28 -1.7(5)
C26 C27 C28 C29 -0.1(5)
C27 C28 C29 C30 1.7(5)
C28 C29 C30 C25 -1.5(5)
C26 C25 C30 C29 -0.2(4)
P2 C25 C30 C29 -177.5(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 436234
