#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/78/2227859.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_2227859
loop_
_publ_author_name
'Nag, Samik'
'Cibian, Mihaela'
'Hanan, Garry S.'
_publ_section_title
;
 8-(Diphenylphosphanyl)quinoline
;
_journal_coeditor_code           NK2063
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2847
_journal_paper_doi               10.1107/S1600536810040237
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C21 H16 N P'
_chemical_formula_moiety         'C21 H16 N P'
_chemical_formula_sum            'C21 H16 N P'
_chemical_formula_weight         313.32
_chemical_name_systematic
;
8-(Diphenylphosphanyl)quinoline
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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
_cell_angle_beta                 112.6510(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7804(2)
_cell_length_b                   16.6905(3)
_cell_length_c                   9.7753(2)
_cell_measurement_reflns_used    9934
_cell_measurement_temperature    150
_cell_measurement_theta_max      72.27
_cell_measurement_theta_min      4.44
_cell_volume                     1623.21(5)
_computing_cell_refinement       'SAINT (Bruker 2007)'
_computing_data_collection       'APEX2 (Bruker 2007)'
_computing_data_reduction        'SAINT (Bruker 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'UdMX (Maris, 2004)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 5.5
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'Helios optics'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_av_sigmaI/netI    0.0127
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            20905
_diffrn_reflns_theta_full        72.44
_diffrn_reflns_theta_max         72.44
_diffrn_reflns_theta_min         4.44
_exptl_absorpt_coefficient_mu    1.467
_exptl_absorpt_correction_T_max  0.8386
_exptl_absorpt_correction_T_min  0.6575
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.341
_refine_ls_extinction_coef       0.0148(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3170
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0405
_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)+(0.0691P)²+0.4334P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1059
_reflns_number_gt                3067
_reflns_number_total             3170
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            nk2063.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2227859
_cod_database_fobs_code          2227859
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_disorder_assembly
_atom_site_disorder_group
P P1 0.85952(3) 1.005358(18) 0.64679(3) 0.02256(14) Uani d . 1 . .
N N1 0.93166(11) 0.84034(6) 0.73402(12) 0.0271(3) Uani d . 1 . .
C C1 0.97809(14) 0.76959(8) 0.79118(16) 0.0314(3) Uani d . 1 . .
H H1 1.0426 0.7678 0.8901 0.038 Uiso calc R 1 . .
C C2 0.93792(15) 0.69649(8) 0.71462(17) 0.0352(3) Uani d . 1 . .
H H2 0.9740 0.6472 0.7619 0.042 Uiso calc R 1 . .
C C3 0.84690(14) 0.69733(8) 0.57230(17) 0.0337(3) Uani d . 1 . .
H H3 0.8207 0.6488 0.5181 0.040 Uiso calc R 1 . .
C C4 0.79150(13) 0.77131(7) 0.50553(15) 0.0270(3) Uani d . 1 . .
C C5 0.69380(14) 0.77770(8) 0.35912(16) 0.0319(3) Uani d . 1 . .
H H5 0.6625 0.7309 0.3007 0.038 Uiso calc R 1 . .
C C6 0.64444(14) 0.85111(8) 0.30167(15) 0.0320(3) Uani d . 1 . .
H H6 0.5788 0.8549 0.2035 0.038 Uiso calc R 1 . .
C C7 0.69018(13) 0.92151(8) 0.38711(14) 0.0276(3) Uani d . 1 . .
H H7 0.6544 0.9720 0.3455 0.033 Uiso calc R 1 . .
C C8 0.78570(12) 0.91807(7) 0.52963(13) 0.0229(3) Uani d . 1 . .
C C9 0.83787(12) 0.84184(7) 0.59135(14) 0.0238(3) Uani d . 1 . .
C C10 0.76718(12) 1.08881(7) 0.52806(13) 0.0236(3) Uani d . 1 . .
C C11 0.66326(13) 1.13098(8) 0.54748(14) 0.0282(3) Uani d . 1 . .
H H11 0.6300 1.1134 0.6193 0.034 Uiso calc R 1 . .
C C12 0.60791(15) 1.19864(8) 0.46244(16) 0.0337(3) Uani d . 1 . .
H H12 0.5381 1.2273 0.4775 0.040 Uiso calc R 1 . .
C C13 0.65439(15) 1.22434(9) 0.35592(16) 0.0343(3) Uani d . 1 . .
H H13 0.6172 1.2708 0.2988 0.041 Uiso calc R 1 . .
C C14 0.75532(14) 1.18199(9) 0.33304(16) 0.0345(3) Uani d . 1 . .
H H14 0.7853 1.1985 0.2580 0.041 Uiso calc R 1 . .
C C15 0.81267(13) 1.11546(8) 0.41960(15) 0.0298(3) Uani d . 1 . .
H H15 0.8836 1.0877 0.4051 0.036 Uiso calc R 1 . .
C C16 0.77946(14) 1.00053(7) 0.78177(15) 0.0243(3) Uani d . 1 . .
C C17 0.66076(13) 0.95868(7) 0.75734(15) 0.0275(3) Uani d . 1 . .
H H17 0.6172 0.9308 0.6666 0.033 Uiso calc R 1 . .
C C18 0.60580(14) 0.95742(8) 0.86437(16) 0.0326(3) Uani d . 1 . .
H H18 0.5249 0.9288 0.8467 0.039 Uiso calc R 1 . .
C C19 0.66880(17) 0.99806(8) 0.99754(17) 0.0361(4) Uani d . 1 . .
H H19 0.6311 0.9971 1.0708 0.043 Uiso calc R 1 . .
C C20 0.78696(15) 1.04008(9) 1.02311(15) 0.0367(3) Uani d . 1 . .
H H20 0.8300 1.0680 1.1138 0.044 Uiso calc R 1 . .
C C21 0.84206(14) 1.04117(8) 0.91598(15) 0.0308(3) Uani d . 1 . .
H H21 0.9230 1.0698 0.9341 0.037 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 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 P1 C16 . . . 101.70(6) y
C8 P1 C10 . . . 102.01(6) y
C16 P1 C10 . . . 101.34(6) y
C1 N1 C9 . . . 117.24(11) y
N1 C1 C2 . . . 124.12(13) no
N1 C1 H1 . . . 117.9 no
C2 C1 H1 . . . 117.9 no
C3 C2 C1 . . . 119.18(12) no
C3 C2 H2 . . . 120.4 no
C1 C2 H2 . . . 120.4 no
C2 C3 C4 . . . 119.39(13) no
C2 C3 H3 . . . 120.3 no
C4 C3 H3 . . . 120.3 no
C3 C4 C5 . . . 123.26(12) no
C3 C4 C9 . . . 117.40(12) no
C5 C4 C9 . . . 119.33(12) no
C6 C5 C4 . . . 120.18(12) no
C6 C5 H5 . . . 119.9 no
C4 C5 H5 . . . 119.9 no
C5 C6 C7 . . . 120.63(12) no
C5 C6 H6 . . . 119.7 no
C7 C6 H6 . . . 119.7 no
C8 C7 C6 . . . 121.10(12) no
C8 C7 H7 . . . 119.4 no
C6 C7 H7 . . . 119.4 no
C7 C8 C9 . . . 118.93(11) no
C7 C8 P1 . . . 124.99(9) no
C9 C8 P1 . . . 116.00(9) no
N1 C9 C4 . . . 122.64(11) no
N1 C9 C8 . . . 117.52(11) no
C4 C9 C8 . . . 119.83(11) no
C11 C10 C15 . . . 118.41(12) no
C11 C10 P1 . . . 124.26(10) no
C15 C10 P1 . . . 117.09(10) no
C12 C11 C10 . . . 120.61(12) no
C12 C11 H11 . . . 119.7 ?
C10 C11 H11 . . . 119.7 ?
C13 C12 C11 . . . 120.23(13) no
C13 C12 H12 . . . 119.9 ?
C11 C12 H12 . . . 119.9 ?
C14 C13 C12 . . . 119.79(13) no
C14 C13 H13 . . . 120.1 ?
C12 C13 H13 . . . 120.1 ?
C13 C14 C15 . . . 120.16(13) no
C13 C14 H14 . . . 119.9 ?
C15 C14 H14 . . . 119.9 ?
C14 C15 C10 . . . 120.76(12) no
C14 C15 H15 . . . 119.6 ?
C10 C15 H15 . . . 119.6 ?
C17 C16 C21 . . . 118.87(12) no
C17 C16 P1 . . . 123.58(10) no
C21 C16 P1 . . . 117.55(10) no
C18 C17 C16 . . . 120.56(13) no
C18 C17 H17 . . . 119.7 ?
C16 C17 H17 . . . 119.7 ?
C17 C18 C19 . . . 120.14(14) no
C17 C18 H18 . . . 119.9 ?
C19 C18 H18 . . . 119.9 ?
C20 C19 C18 . . . 119.85(13) no
C20 C19 H19 . . . 120.1 ?
C18 C19 H19 . . . 120.1 ?
C21 C20 C19 . . . 119.97(13) no
C21 C20 H20 . . . 120.0 ?
C19 C20 H20 . . . 120.0 ?
C20 C21 C16 . . . 120.61(13) no
C20 C21 H21 . . . 119.7 ?
C16 C21 H21 . . . 119.7 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 C8 . . 1.8345(12) y
P1 C16 . . 1.8357(14) y
P1 C10 . . 1.8408(12) y
N1 C1 . . 1.3196(17) y
N1 C9 . . 1.3718(16) no
C1 C2 . . 1.410(2) no
C1 H1 . . 0.9500 no
C2 C3 . . 1.359(2) no
C2 H2 . . 0.9500 no
C3 C4 . . 1.4167(19) no
C3 H3 . . 0.9500 no
C4 C5 . . 1.417(2) no
C4 C9 . . 1.4200(17) no
C5 C6 . . 1.367(2) no
C5 H5 . . 0.9500 no
C6 C7 . . 1.4158(18) no
C6 H6 . . 0.9500 no
C7 C8 . . 1.3783(18) no
C7 H7 . . 0.9500 no
C8 C9 . . 1.4275(16) no
C10 C11 . . 1.3964(18) no
C10 C15 . . 1.4010(18) no
C11 C12 . . 1.3930(18) no
C11 H11 . . 0.9500 no
C12 C13 . . 1.386(2) no
C12 H12 . . 0.9500 no
C13 C14 . . 1.386(2) no
C13 H13 . . 0.9500 no
C14 C15 . . 1.3887(19) no
C14 H14 . . 0.9500 no
C15 H15 . . 0.9500 no
C16 C17 . . 1.3953(18) no
C16 C21 . . 1.3982(18) no
C17 C18 . . 1.3869(19) no
C17 H17 . . 0.9500 no
C18 C19 . . 1.391(2) no
C18 H18 . . 0.9500 no
C19 C20 . . 1.390(2) no
C19 H19 . . 0.9500 no
C20 C21 . . 1.389(2) no
C20 H20 . . 0.9500 no
C21 H21 . . 0.9500 no
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9 N1 C1 C2 . . . . 0.41(19) no
N1 C1 C2 C3 . . . . 0.8(2) no
C1 C2 C3 C4 . . . . -1.8(2) no
C2 C3 C4 C5 . . . . -178.48(13) no
C2 C3 C4 C9 . . . . 1.73(19) no
C3 C4 C5 C6 . . . . 179.91(13) no
C9 C4 C5 C6 . . . . -0.3(2) no
C4 C5 C6 C7 . . . . 0.1(2) no
C5 C6 C7 C8 . . . . 0.3(2) no
C6 C7 C8 C9 . . . . -0.50(19) no
C6 C7 C8 P1 . . . . 176.31(10) no
C16 P1 C8 C7 . . . . 107.19(11) no
C10 P1 C8 C7 . . . . 2.74(13) no
C16 P1 C8 C9 . . . . -75.92(10) no
C10 P1 C8 C9 . . . . 179.64(9) no
C1 N1 C9 C4 . . . . -0.49(18) no
C1 N1 C9 C8 . . . . 179.06(11) no
C3 C4 C9 N1 . . . . -0.56(18) no
C5 C4 C9 N1 . . . . 179.64(11) no
C3 C4 C9 C8 . . . . 179.90(11) no
C5 C4 C9 C8 . . . . 0.09(18) no
C7 C8 C9 N1 . . . . -179.27(11) no
P1 C8 C9 N1 . . . . 3.64(15) no
C7 C8 C9 C4 . . . . 0.30(18) no
P1 C8 C9 C4 . . . . -176.79(9) no
C8 P1 C10 C11 . . . . 103.60(11) no
C16 P1 C10 C11 . . . . -1.13(12) no
C8 P1 C10 C15 . . . . -82.02(11) no
C16 P1 C10 C15 . . . . 173.26(10) no
C15 C10 C11 C12 . . . . -1.01(19) no
P1 C10 C11 C12 . . . . 173.30(10) no
C10 C11 C12 C13 . . . . 0.8(2) no
C11 C12 C13 C14 . . . . 0.7(2) no
C12 C13 C14 C15 . . . . -2.0(2) no
C13 C14 C15 C10 . . . . 1.8(2) no
C11 C10 C15 C14 . . . . -0.30(19) no
P1 C10 C15 C14 . . . . -175.03(11) no
C8 P1 C16 C17 . . . . -20.27(12) no
C10 P1 C16 C17 . . . . 84.70(11) no
C8 P1 C16 C21 . . . . 159.62(10) no
C10 P1 C16 C21 . . . . -95.41(11) no
C21 C16 C17 C18 . . . . 0.00(19) no
P1 C16 C17 C18 . . . . 179.90(10) no
C16 C17 C18 C19 . . . . 0.0(2) no
C17 C18 C19 C20 . . . . 0.1(2) no
C18 C19 C20 C21 . . . . -0.2(2) no
C19 C20 C21 C16 . . . . 0.2(2) no
C17 C16 C21 C20 . . . . -0.13(19) no
P1 C16 C21 C20 . . . . 179.97(10) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 545995
