#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/78/2237869.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_2237869
loop_
_publ_author_name
'Chen, Chen'
'Wang, Kun-Yan'
'Liu, Jin-Fang'
'Wang, Dan-Feng'
'Zhu, Hong-Jun'
_publ_section_title
;
 4-Diphenylphosphanyl-8-methyl-1,5-naphthyridine
;
_journal_coeditor_code           HB7082
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o928
_journal_paper_doi               10.1107/S1600536813013196
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C21 H17 N2 P'
_chemical_formula_moiety         'C21 H17 N2 P'
_chemical_formula_sum            'C21 H17 N2 P'
_chemical_formula_weight         328.34
_chemical_name_systematic
;
4-Diphenylphosphanyl-8-methyl-1,5-naphthyridine
;
_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
_cell_angle_alpha                99.78(3)
_cell_angle_beta                 93.35(3)
_cell_angle_gamma                98.58(3)
_cell_formula_units_Z            2
_cell_length_a                   7.2320(14)
_cell_length_b                   7.4470(15)
_cell_length_c                   16.780(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      10
_cell_volume                     877.4(3)
_computing_cell_refinement       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_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_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0379
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3500
_diffrn_reflns_theta_full        25.37
_diffrn_reflns_theta_max         25.37
_diffrn_reflns_theta_min         1.24
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_T_max  0.9842
_exptl_absorpt_correction_T_min  0.9536
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.230
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3224
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0502
_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)+(0.0960P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1327
_refine_ls_wR_factor_ref         0.1545
_reflns_number_gt                2285
_reflns_number_total             3224
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb7082.cif
_cod_data_source_block           I
_cod_database_code               2237869
_cod_database_fobs_code          2237869
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
_atom_site_symmetry_multiplicity
P P 0.18105(10) 0.17196(9) 0.71974(4) 0.0529(2) Uani d . 1 1
N N1 0.2284(3) 0.3164(3) 0.89550(13) 0.0603(6) Uani d . 1 1
C C1 -0.0068(5) -0.0965(4) 0.59708(17) 0.0711(8) Uani d . 1 1
H H1B -0.1116 -0.0650 0.6223 0.085 Uiso calc R 1 1
N N2 0.2453(3) -0.1579(3) 0.92992(13) 0.0569(6) Uani d . 1 1
C C2 -0.0308(6) -0.2312(5) 0.5287(2) 0.0906(11) Uani d . 1 1
H H2B -0.1507 -0.2917 0.5087 0.109 Uiso calc R 1 1
C C3 0.1213(7) -0.2762(5) 0.4901(2) 0.0976(13) Uani d . 1 1
H H3A 0.1048 -0.3655 0.4432 0.117 Uiso calc R 1 1
C C4 0.2974(6) -0.1907(5) 0.5202(2) 0.0914(11) Uani d . 1 1
H H4A 0.4009 -0.2230 0.4942 0.110 Uiso calc R 1 1
C C5 0.3227(5) -0.0553(4) 0.58980(18) 0.0734(8) Uani d . 1 1
H H5A 0.4433 0.0028 0.6098 0.088 Uiso calc R 1 1
C C6 0.1710(4) -0.0060(3) 0.62951(15) 0.0579(7) Uani d . 1 1
C C7 0.4103(3) 0.3111(3) 0.71826(14) 0.0501(6) Uani d . 1 1
C C8 0.5758(4) 0.2855(4) 0.75679(17) 0.0644(7) Uani d . 1 1
H H8A 0.5754 0.1889 0.7854 0.077 Uiso calc R 1 1
C C9 0.7416(4) 0.4013(4) 0.75339(19) 0.0757(8) Uani d . 1 1
H H9A 0.8516 0.3842 0.7806 0.091 Uiso calc R 1 1
C C10 0.7445(5) 0.5412(4) 0.7101(2) 0.0822(10) Uani d . 1 1
H H10A 0.8568 0.6181 0.7071 0.099 Uiso calc R 1 1
C C11 0.5835(5) 0.5682(4) 0.6713(2) 0.0844(10) Uani d . 1 1
H H11A 0.5859 0.6635 0.6419 0.101 Uiso calc R 1 1
C C12 0.4175(4) 0.4557(3) 0.67539(17) 0.0652(7) Uani d . 1 1
H H12A 0.3080 0.4764 0.6491 0.078 Uiso calc R 1 1
C C13 0.2210(3) 0.0390(3) 0.79998(14) 0.0476(6) Uani d . 1 1
C C14 0.2313(3) 0.1306(3) 0.88168(14) 0.0468(6) Uani d . 1 1
C C15 0.2393(5) 0.3962(4) 0.97172(18) 0.0744(9) Uani d . 1 1
H H15A 0.2379 0.5226 0.9827 0.089 Uiso calc R 1 1
C C16 0.2527(4) 0.3065(4) 1.03778(18) 0.0736(8) Uani d . 1 1
H H16A 0.2609 0.3736 1.0903 0.088 Uiso calc R 1 1
C C17 0.2539(3) 0.1222(4) 1.02590(15) 0.0557(6) Uani d . 1 1
C C18 0.2437(3) 0.0284(3) 0.94493(15) 0.0478(6) Uani d . 1 1
C C19 0.2366(4) -0.2382(3) 0.85361(17) 0.0638(7) Uani d . 1 1
H H19A 0.2389 -0.3645 0.8426 0.077 Uiso calc R 1 1
C C20 0.2241(4) -0.1471(3) 0.78760(16) 0.0576(6) Uani d . 1 1
H H20A 0.2179 -0.2133 0.7350 0.069 Uiso calc R 1 1
C C21 0.2657(4) 0.0179(4) 1.09549(16) 0.0724(8) Uani d . 1 1
H H21A 0.2718 0.1022 1.1460 0.109 Uiso calc R 1 1
H H21B 0.3761 -0.0394 1.0935 0.109 Uiso calc R 1 1
H H21C 0.1565 -0.0752 1.0911 0.109 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'
N N 0.0061 0.0033 '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
C7 P C6 102.31(12) n
C7 P C13 102.97(11) n
C6 P C13 100.69(11) n
C15 N1 C14 115.8(2) n
C2 C1 C6 121.5(3) ?
C2 C1 H1B 119.3 ?
C6 C1 H1B 119.3 ?
C19 N2 C18 116.9(2) n
C3 C2 C1 119.9(3) ?
C3 C2 H2B 120.0 ?
C1 C2 H2B 120.0 ?
C4 C3 C2 120.2(3) ?
C4 C3 H3A 119.9 ?
C2 C3 H3A 119.9 ?
C3 C4 C5 120.1(4) ?
C3 C4 H4A 119.9 ?
C5 C4 H4A 119.9 ?
C6 C5 C4 120.8(3) ?
C6 C5 H5A 119.6 ?
C4 C5 H5A 119.6 ?
C5 C6 C1 117.5(3) ?
C5 C6 P 125.9(2) ?
C1 C6 P 116.6(2) ?
C8 C7 C12 117.7(2) ?
C8 C7 P 125.38(19) ?
C12 C7 P 116.9(2) ?
C9 C8 C7 120.8(3) ?
C9 C8 H8A 119.6 ?
C7 C8 H8A 119.6 ?
C10 C9 C8 120.1(3) ?
C10 C9 H9A 120.0 ?
C8 C9 H9A 120.0 ?
C11 C10 C9 120.0(3) ?
C11 C10 H10A 120.0 ?
C9 C10 H10A 120.0 ?
C10 C11 C12 120.4(3) ?
C10 C11 H11A 119.8 ?
C12 C11 H11A 119.8 ?
C11 C12 C7 121.0(3) ?
C11 C12 H12A 119.5 ?
C7 C12 H12A 119.5 ?
C20 C13 C14 116.6(2) ?
C20 C13 P 125.1(2) ?
C14 C13 P 117.97(16) ?
N1 C14 C18 122.9(2) ?
N1 C14 C13 117.7(2) ?
C18 C14 C13 119.5(2) ?
N1 C15 C16 125.1(2) ?
N1 C15 H15A 117.4 ?
C16 C15 H15A 117.4 ?
C17 C16 C15 120.3(3) ?
C17 C16 H16A 119.8 ?
C15 C16 H16A 119.8 ?
C16 C17 C18 117.2(2) ?
C16 C17 C21 122.4(3) ?
C18 C17 C21 120.4(2) ?
N2 C18 C17 119.3(2) ?
N2 C18 C14 122.1(2) ?
C17 C18 C14 118.6(2) ?
N2 C19 C20 124.6(2) ?
N2 C19 H19A 117.7 ?
C20 C19 H19A 117.7 ?
C13 C20 C19 120.4(2) ?
C13 C20 H20A 119.8 ?
C19 C20 H20A 119.8 ?
C17 C21 H21A 109.5 ?
C17 C21 H21B 109.5 ?
H21A C21 H21B 109.5 ?
C17 C21 H21C 109.5 ?
H21A C21 H21C 109.5 ?
H21B C21 H21C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
P C7 1.823(3) n
P C6 1.825(3) n
P C13 1.836(2) n
N1 C15 1.308(3) n
N1 C14 1.367(3) n
C1 C2 1.374(4) ?
C1 C6 1.392(4) ?
C1 H1B 0.9300 ?
N2 C19 1.312(3) n
N2 C18 1.369(3) n
C2 C3 1.364(5) ?
C2 H2B 0.9300 ?
C3 C4 1.362(5) ?
C3 H3A 0.9300 ?
C4 C5 1.391(4) ?
C4 H4A 0.9300 ?
C5 C6 1.380(4) ?
C5 H5A 0.9300 ?
C7 C8 1.381(4) ?
C7 C12 1.390(3) ?
C8 C9 1.379(4) ?
C8 H8A 0.9300 ?
C9 C10 1.367(4) ?
C9 H9A 0.9300 ?
C10 C11 1.358(5) ?
C10 H10A 0.9300 ?
C11 C12 1.369(4) ?
C11 H11A 0.9300 ?
C12 H12A 0.9300 ?
C13 C20 1.370(3) ?
C13 C14 1.416(3) ?
C14 C18 1.413(3) ?
C15 C16 1.394(4) ?
C15 H15A 0.9300 ?
C16 C17 1.355(4) ?
C16 H16A 0.9300 ?
C17 C18 1.411(3) ?
C17 C21 1.513(3) ?
C19 C20 1.399(3) ?
C19 H19A 0.9300 ?
C20 H20A 0.9300 ?
C21 H21A 0.9600 ?
C21 H21B 0.9600 ?
C21 H21C 0.9600 ?
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
C6 C1 C2 C3 -1.3(5)
C1 C2 C3 C4 1.4(5)
C2 C3 C4 C5 -0.9(5)
C3 C4 C5 C6 0.3(5)
C4 C5 C6 C1 -0.2(4)
C4 C5 C6 P -178.5(2)
C2 C1 C6 C5 0.7(4)
C2 C1 C6 P 179.2(2)
C7 P C6 C5 19.7(3)
C13 P C6 C5 -86.2(2)
C7 P C6 C1 -158.59(19)
C13 P C6 C1 95.5(2)
C6 P C7 C8 -91.8(2)
C13 P C7 C8 12.4(2)
C6 P C7 C12 88.9(2)
C13 P C7 C12 -166.89(19)
C12 C7 C8 C9 0.7(4)
P C7 C8 C9 -178.5(2)
C7 C8 C9 C10 -1.4(4)
C8 C9 C10 C11 1.0(5)
C9 C10 C11 C12 0.0(5)
C10 C11 C12 C7 -0.7(5)
C8 C7 C12 C11 0.3(4)
P C7 C12 C11 179.6(2)
C7 P C13 C20 -110.0(2)
C6 P C13 C20 -4.6(3)
C7 P C13 C14 76.6(2)
C6 P C13 C14 -178.00(19)
C15 N1 C14 C18 0.5(4)
C15 N1 C14 C13 -179.6(2)
C20 C13 C14 N1 -180.0(2)
P C13 C14 N1 -6.0(3)
C20 C13 C14 C18 -0.1(3)
P C13 C14 C18 173.91(17)
C14 N1 C15 C16 -0.2(5)
N1 C15 C16 C17 -0.5(5)
C15 C16 C17 C18 0.9(4)
C15 C16 C17 C21 -179.2(3)
C19 N2 C18 C17 -179.6(2)
C19 N2 C18 C14 0.7(3)
C16 C17 C18 N2 179.7(2)
C21 C17 C18 N2 -0.2(3)
C16 C17 C18 C14 -0.6(4)
C21 C17 C18 C14 179.5(2)
N1 C14 C18 N2 179.6(2)
C13 C14 C18 N2 -0.3(3)
N1 C14 C18 C17 -0.1(4)
C13 C14 C18 C17 180.0(2)
C18 N2 C19 C20 -0.7(4)
C14 C13 C20 C19 0.1(4)
P C13 C20 C19 -173.4(2)
N2 C19 C20 C13 0.3(4)
