#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/53/2235347.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_2235347
loop_
_publ_author_name
'Niu, Feng'
'Chai, Wenxiang'
'Song, Li'
'Zhou, Mengbo'
'Liang, Jiaping'
_publ_section_title
;
 rac-2,2'-Bis(diphenylphosphanyl)-1,1'-binaphthyl: a racemic
 diphosphine ligand
;
_journal_coeditor_code           BG2467
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2033
_journal_paper_doi               10.1107/S1600536812025603
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C44 H32 P2'
_chemical_formula_moiety         'C44 H32 P2'
_chemical_formula_sum            'C44 H32 P2'
_chemical_formula_weight         622.64
_chemical_name_common            BINAP
_chemical_name_systematic
;
rac-2,2'-Bis(diphenylphosphanyl)-1,1'-binaphthyl
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 107.904(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.6120(8)
_cell_length_b                   9.2008(3)
_cell_length_c                   19.1240(9)
_cell_measurement_reflns_used    2381
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5208
_cell_measurement_theta_min      3.5442
_cell_volume                     3283.7(2)
_computing_cell_refinement       'CrysAlisPro  (Oxford Diffraction, 2011)'
_computing_data_collection       'CrysAlisPro (Oxford Diffraction, 2011)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction, 2011)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0379
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6234
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         3.55
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_T_max  0.9679
_exptl_absorpt_correction_T_min  0.9540
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.221
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3052
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0415
_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)+(0.0387P)²+1.4219P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0994
_reflns_number_gt                2314
_reflns_number_total             3052
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bg2467.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2235347
_cod_database_fobs_code          2235347
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
_atom_site_symmetry_multiplicity
P P1 0.43987(2) 0.96498(5) 0.13904(3) 0.03969(16) Uani d . 1 1
C C1 0.41174(9) 1.08276(19) 0.20272(9) 0.0348(4) Uani d . 1 1
C C2 0.46167(8) 1.17151(17) 0.25019(9) 0.0316(4) Uani d . 1 1
C C3 0.44162(9) 1.26196(19) 0.30150(9) 0.0368(4) Uani d . 1 1
C C4 0.49012(11) 1.3589(2) 0.34918(11) 0.0492(5) Uani d . 1 1
H H4 0.5364 1.3677 0.3463 0.059 Uiso calc R 1 1
C C5 0.47017(14) 1.4398(3) 0.39936(12) 0.0680(7) Uani d . 1 1
H H5 0.5027 1.5037 0.4299 0.082 Uiso calc R 1 1
C C6 0.40094(15) 1.4271(3) 0.40508(13) 0.0718(7) Uani d . 1 1
H H6 0.3882 1.4804 0.4405 0.086 Uiso calc R 1 1
C C7 0.35255(13) 1.3379(2) 0.35949(13) 0.0609(6) Uani d . 1 1
H H7 0.3066 1.3314 0.3636 0.073 Uiso calc R 1 1
C C8 0.37053(10) 1.2543(2) 0.30552(11) 0.0434(5) Uani d . 1 1
C C9 0.32087(10) 1.1626(2) 0.25612(12) 0.0489(5) Uani d . 1 1
H H9 0.2740 1.1582 0.2576 0.059 Uiso calc R 1 1
C C10 0.34033(9) 1.0807(2) 0.20647(11) 0.0450(5) Uani d . 1 1
H H10 0.3063 1.0219 0.1742 0.054 Uiso calc R 1 1
C C11 0.38645(9) 0.8015(2) 0.13995(11) 0.0422(5) Uani d . 1 1
C C12 0.39753(10) 0.7322(2) 0.20704(12) 0.0524(5) Uani d . 1 1
H H12 0.4278 0.7746 0.2494 0.063 Uiso calc R 1 1
C C13 0.36481(11) 0.6022(2) 0.21238(13) 0.0581(6) Uani d . 1 1
H H13 0.3728 0.5583 0.2580 0.070 Uiso calc R 1 1
C C14 0.32063(12) 0.5375(2) 0.15075(15) 0.0634(6) Uani d . 1 1
H H14 0.2987 0.4493 0.1543 0.076 Uiso calc R 1 1
C C15 0.30870(12) 0.6029(2) 0.08377(15) 0.0686(7) Uani d . 1 1
H H15 0.2786 0.5588 0.0418 0.082 Uiso calc R 1 1
C C16 0.34129(11) 0.7350(2) 0.07787(12) 0.0585(6) Uani d . 1 1
H H16 0.3327 0.7787 0.0321 0.070 Uiso calc R 1 1
C C17 0.39622(9) 1.0482(2) 0.04936(10) 0.0404(4) Uani d . 1 1
C C18 0.35445(10) 1.1731(2) 0.03891(11) 0.0472(5) Uani d . 1 1
H H18 0.3428 1.2137 0.0783 0.057 Uiso calc R 1 1
C C19 0.32997(11) 1.2376(2) -0.02968(12) 0.0573(6) Uani d . 1 1
H H19 0.3017 1.3206 -0.0359 0.069 Uiso calc R 1 1
C C20 0.34691(12) 1.1805(3) -0.08887(12) 0.0617(6) Uani d . 1 1
H H20 0.3309 1.2253 -0.1346 0.074 Uiso calc R 1 1
C C21 0.38763(12) 1.0571(3) -0.07949(12) 0.0611(6) Uani d . 1 1
H H21 0.3987 1.0171 -0.1193 0.073 Uiso calc R 1 1
C C22 0.41240(11) 0.9914(2) -0.01138(12) 0.0529(5) Uani d . 1 1
H H22 0.4403 0.9079 -0.0059 0.063 Uiso calc R 1 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_site_symmetry_3
_geom_angle
C17 P1 C11 . 104.33(8)
C17 P1 C1 . 102.99(8)
C11 P1 C1 . 100.87(8)
C2 C1 C10 . 119.00(16)
C2 C1 P1 . 119.23(12)
C10 C1 P1 . 121.72(14)
C1 C2 C3 . 120.43(15)
C1 C2 C2 2_655 120.30(15)
C3 C2 C2 2_655 119.25(15)
C4 C3 C8 . 118.24(17)
C4 C3 C2 . 122.49(16)
C8 C3 C2 . 119.27(16)
C5 C4 C3 . 121.1(2)
C5 C4 H4 . 119.4
C3 C4 H4 . 119.4
C4 C5 C6 . 120.3(2)
C4 C5 H5 . 119.8
C6 C5 H5 . 119.8
C7 C6 C5 . 120.4(2)
C7 C6 H6 . 119.8
C5 C6 H6 . 119.8
C6 C7 C8 . 121.2(2)
C6 C7 H7 . 119.4
C8 C7 H7 . 119.4
C9 C8 C7 . 122.56(19)
C9 C8 C3 . 118.73(17)
C7 C8 C3 . 118.71(19)
C10 C9 C8 . 121.12(17)
C10 C9 H9 . 119.4
C8 C9 H9 . 119.4
C9 C10 C1 . 121.37(18)
C9 C10 H10 . 119.3
C1 C10 H10 . 119.3
C16 C11 C12 . 117.79(18)
C16 C11 P1 . 124.71(16)
C12 C11 P1 . 117.20(14)
C13 C12 C11 . 121.6(2)
C13 C12 H12 . 119.2
C11 C12 H12 . 119.2
C14 C13 C12 . 120.1(2)
C14 C13 H13 . 119.9
C12 C13 H13 . 119.9
C13 C14 C15 . 119.7(2)
C13 C14 H14 . 120.1
C15 C14 H14 . 120.1
C14 C15 C16 . 120.6(2)
C14 C15 H15 . 119.7
C16 C15 H15 . 119.7
C11 C16 C15 . 120.2(2)
C11 C16 H16 . 119.9
C15 C16 H16 . 119.9
C18 C17 C22 . 117.69(19)
C18 C17 P1 . 124.43(15)
C22 C17 P1 . 117.50(15)
C19 C18 C17 . 120.55(19)
C19 C18 H18 . 119.7
C17 C18 H18 . 119.7
C20 C19 C18 . 120.9(2)
C20 C19 H19 . 119.5
C18 C19 H19 . 119.5
C21 C20 C19 . 119.1(2)
C21 C20 H20 . 120.4
C19 C20 H20 . 120.4
C20 C21 C22 . 120.6(2)
C20 C21 H21 . 119.7
C22 C21 H21 . 119.7
C21 C22 C17 . 121.1(2)
C21 C22 H22 . 119.5
C17 C22 H22 . 119.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
P1 C17 . 1.833(2)
P1 C11 . 1.8364(19)
P1 C1 . 1.8370(18)
C1 C2 . 1.380(2)
C1 C10 . 1.424(2)
C2 C3 . 1.431(2)
C2 C2 2_655 1.506(3)
C3 C4 . 1.414(3)
C3 C8 . 1.421(2)
C4 C5 . 1.363(3)
C4 H4 . 0.9300
C5 C6 . 1.400(3)
C5 H5 . 0.9300
C6 C7 . 1.351(3)
C6 H6 . 0.9300
C7 C8 . 1.416(3)
C7 H7 . 0.9300
C8 C9 . 1.410(3)
C9 C10 . 1.356(3)
C9 H9 . 0.9300
C10 H10 . 0.9300
C11 C16 . 1.386(3)
C11 C12 . 1.389(3)
C12 C13 . 1.376(3)
C12 H12 . 0.9300
C13 C14 . 1.366(3)
C13 H13 . 0.9300
C14 C15 . 1.369(3)
C14 H14 . 0.9300
C15 C16 . 1.394(3)
C15 H15 . 0.9300
C16 H16 . 0.9300
C17 C18 . 1.389(3)
C17 C22 . 1.397(3)
C18 C19 . 1.384(3)
C18 H18 . 0.9300
C19 C20 . 1.378(3)
C19 H19 . 0.9300
C20 C21 . 1.368(3)
C20 H20 . 0.9300
C21 C22 . 1.382(3)
C21 H21 . 0.9300
C22 H22 . 0.9300
