#------------------------------------------------------------------------------
#$Date: 2023-05-10 09:37:06 +0300 (Wed, 10 May 2023) $
#$Revision: 283639 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/71/8107157.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_8107157
loop_
_publ_author_name
'Wu, Gui-Ling'
_publ_section_title
;
 The crystal structure of tris(6-methylpyridin-2-yl)phosphine oxide,
 C18H18N3OP
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              577
_journal_page_last               578
_journal_paper_doi               10.1515/ncrs-2022-0137
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C18 H18 N3 O P'
_chemical_formula_sum            'C18 H18 N3 O P'
_chemical_formula_weight         323.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 95.849(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.3987(17)
_cell_length_b                   8.7084(11)
_cell_length_c                   14.5063(18)
_cell_measurement_reflns_used    7614
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      31.33
_cell_measurement_theta_min      2.73
_cell_volume                     1683.8(4)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17391
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_min         1.971
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_T_max  0.9748
_exptl_absorpt_correction_T_min  0.9666
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         4874
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0423
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0910P)²+0.2233P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1311
_refine_ls_wR_factor_ref         0.1409
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4110
_reflns_number_total             4874
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0137_suppl.cif
_cod_data_source_block           t
_cod_database_code               8107157
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.967
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C8(H8), C9(H9), C10(H10), C14(H14), C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C12(H12A,H12B,H12C), C18(H18A,H18B,H18C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.20237(9) 0.39276(13) 0.01454(9) 0.0295(2) Uani 1 1 d . . . . .
C2 C 0.10769(10) 0.33947(16) -0.01556(10) 0.0379(3) Uani 1 1 d . . . . .
H2 H 0.052390 0.404546 -0.019349 0.045 Uiso 1 1 calc R . . . .
C3 C 0.09743(11) 0.18528(18) -0.04007(11) 0.0435(3) Uani 1 1 d . . . . .
H3 H 0.034669 0.145247 -0.060366 0.052 Uiso 1 1 calc R . . . .
C4 C 0.18077(11) 0.09306(16) -0.03401(11) 0.0414(3) Uani 1 1 d . . . . .
H4 H 0.175008 -0.010401 -0.049524 0.050 Uiso 1 1 calc R . . . .
C5 C 0.27455(10) 0.15616(15) -0.00425(10) 0.0367(3) Uani 1 1 d . . . . .
C6 C 0.36779(14) 0.0606(2) 0.00085(17) 0.0621(5) Uani 1 1 d . . . . .
H6A H 0.425473 0.126482 0.004285 0.093 Uiso 1 1 calc GR . . . .
H6B H 0.366476 -0.002734 -0.053450 0.093 Uiso 1 1 calc GR . . . .
H6C H 0.371224 -0.003415 0.054976 0.093 Uiso 1 1 calc GR . . . .
C7 C 0.30736(10) 0.59480(14) 0.15027(8) 0.0316(3) Uani 1 1 d . . . . .
C8 C 0.30791(12) 0.47758(18) 0.21485(10) 0.0428(3) Uani 1 1 d . . . . .
H8 H 0.267230 0.391623 0.203918 0.051 Uiso 1 1 calc R . . . .
C9 C 0.37124(14) 0.4924(2) 0.29667(11) 0.0539(4) Uani 1 1 d . . . . .
H9 H 0.373590 0.416472 0.341936 0.065 Uiso 1 1 calc R . . . .
C10 C 0.43009(14) 0.6211(2) 0.30918(11) 0.0526(4) Uani 1 1 d . . . . .
H10 H 0.474625 0.631459 0.362336 0.063 Uiso 1 1 calc R . . . .
C11 C 0.42312(12) 0.73576(19) 0.24254(10) 0.0446(3) Uani 1 1 d . . . . .
C12 C 0.48210(18) 0.8826(2) 0.25702(15) 0.0689(6) Uani 1 1 d . . . . .
H12A H 0.517013 0.902554 0.203683 0.103 Uiso 1 1 calc GR . . . .
H12B H 0.529713 0.872717 0.310812 0.103 Uiso 1 1 calc GR . . . .
H12C H 0.437178 0.965946 0.265807 0.103 Uiso 1 1 calc GR . . . .
C13 C 0.29749(9) 0.65975(13) -0.04709(8) 0.0293(2) Uani 1 1 d . . . . .
C14 C 0.39914(11) 0.62984(18) -0.04539(10) 0.0406(3) Uani 1 1 d . . . . .
H14 H 0.434084 0.582368 0.005509 0.049 Uiso 1 1 calc R . . . .
C15 C 0.44766(12) 0.6725(2) -0.12168(12) 0.0486(4) Uani 1 1 d . . . . .
H15 H 0.515656 0.652643 -0.123318 0.058 Uiso 1 1 calc R . . . .
C16 C 0.39368(14) 0.74414(18) -0.19411(11) 0.0482(4) Uani 1 1 d . . . . .
H16 H 0.424722 0.773580 -0.245820 0.058 Uiso 1 1 calc R . . . .
C17 C 0.29182(13) 0.77306(16) -0.19036(10) 0.0438(3) Uani 1 1 d . . . . .
C18 C 0.2302(2) 0.8554(3) -0.26712(14) 0.0754(6) Uani 1 1 d . . . . .
H18A H 0.192526 0.782029 -0.305905 0.113 Uiso 1 1 calc GR . . . .
H18B H 0.273634 0.912121 -0.303350 0.113 Uiso 1 1 calc GR . . . .
H18C H 0.184853 0.924874 -0.241239 0.113 Uiso 1 1 calc GR . . . .
N1 N 0.28517(8) 0.30445(13) 0.01985(8) 0.0338(2) Uani 1 1 d . . . . .
N2 N 0.36249(9) 0.72363(14) 0.16337(8) 0.0383(3) Uani 1 1 d . . . . .
N3 N 0.24404(9) 0.72964(12) -0.11779(8) 0.0357(2) Uani 1 1 d . . . . .
O1 O 0.12973(7) 0.68199(12) 0.05029(8) 0.0422(2) Uani 1 1 d . . . . .
P1 P 0.22329(2) 0.59414(3) 0.04377(2) 0.02815(11) Uani 1 1 d . . . . .
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'
O O 0.0106 0.0060 '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_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 P1 120.87(10) . .
N1 C1 C2 123.51(11) . .
N1 C1 P1 115.53(9) . .
C1 C2 H2 121.0 . .
C1 C2 C3 117.97(12) . .
C3 C2 H2 121.0 . .
C2 C3 H3 120.3 . .
C4 C3 C2 119.34(13) . .
C4 C3 H3 120.3 . .
C3 C4 H4 120.3 . .
C3 C4 C5 119.33(12) . .
C5 C4 H4 120.3 . .
C4 C5 C6 121.05(13) . .
N1 C5 C4 121.77(12) . .
N1 C5 C6 117.18(13) . .
C5 C6 H6A 109.5 . .
C5 C6 H6B 109.5 . .
C5 C6 H6C 109.5 . .
H6A C6 H6B 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
C8 C7 P1 122.20(10) . .
N2 C7 C8 123.63(12) . .
N2 C7 P1 113.99(9) . .
C7 C8 H8 121.0 . .
C7 C8 C9 117.96(14) . .
C9 C8 H8 121.0 . .
C8 C9 H9 120.6 . .
C10 C9 C8 118.71(15) . .
C10 C9 H9 120.6 . .
C9 C10 H10 120.0 . .
C9 C10 C11 119.95(15) . .
C11 C10 H10 120.0 . .
C10 C11 C12 121.12(16) . .
N2 C11 C10 122.15(15) . .
N2 C11 C12 116.71(15) . .
C11 C12 H12A 109.5 . .
C11 C12 H12B 109.5 . .
C11 C12 H12C 109.5 . .
H12A C12 H12B 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C14 C13 P1 122.45(10) . .
N3 C13 C14 123.28(12) . .
N3 C13 P1 114.13(9) . .
C13 C14 H14 120.8 . .
C13 C14 C15 118.33(14) . .
C15 C14 H14 120.8 . .
C14 C15 H15 120.6 . .
C16 C15 C14 118.76(15) . .
C16 C15 H15 120.6 . .
C15 C16 H16 120.1 . .
C15 C16 C17 119.78(14) . .
C17 C16 H16 120.1 . .
C16 C17 C18 121.65(16) . .
N3 C17 C16 121.82(14) . .
N3 C17 C18 116.53(16) . .
C17 C18 H18A 109.5 . .
C17 C18 H18B 109.5 . .
C17 C18 H18C 109.5 . .
H18A C18 H18B 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C5 N1 C1 118.05(11) . .
C11 N2 C7 117.53(13) . .
C13 N3 C17 118.00(13) . .
C1 P1 C13 102.48(5) . .
C7 P1 C1 105.59(6) . .
C7 P1 C13 106.11(6) . .
O1 P1 C1 113.70(6) . .
O1 P1 C7 113.57(6) . .
O1 P1 C13 114.35(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.3793(17) .
C1 N1 1.3456(15) .
C1 P1 1.8192(12) .
C2 H2 0.9300 .
C2 C3 1.392(2) .
C3 H3 0.9300 .
C3 C4 1.371(2) .
C4 H4 0.9300 .
C4 C5 1.399(2) .
C5 C6 1.497(2) .
C5 N1 1.3417(16) .
C6 H6A 0.9600 .
C6 H6B 0.9600 .
C6 H6C 0.9600 .
C7 C8 1.3851(19) .
C7 N2 1.3460(17) .
C7 P1 1.8169(13) .
C8 H8 0.9300 .
C8 C9 1.393(2) .
C9 H9 0.9300 .
C9 C10 1.372(3) .
C10 H10 0.9300 .
C10 C11 1.386(2) .
C11 C12 1.506(2) .
C11 N2 1.3415(19) .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
C13 C14 1.3844(18) .
C13 N3 1.3362(16) .
C13 P1 1.8219(13) .
C14 H14 0.9300 .
C14 C15 1.390(2) .
C15 H15 0.9300 .
C15 C16 1.364(3) .
C16 H16 0.9300 .
C16 C17 1.394(2) .
C17 C18 1.500(2) .
C17 N3 1.3410(19) .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
O1 P1 1.4798(9) .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 C2 C3 C4 -0.3(2) . . . .
C2 C1 N1 C5 -1.0(2) . . . .
C2 C1 P1 C7 136.82(11) . . . .
C2 C1 P1 C13 -112.28(11) . . . .
C2 C1 P1 O1 11.66(13) . . . .
C2 C3 C4 C5 -0.7(2) . . . .
C3 C4 C5 C6 -178.29(17) . . . .
C3 C4 C5 N1 0.9(2) . . . .
C4 C5 N1 C1 -0.1(2) . . . .
C6 C5 N1 C1 179.13(15) . . . .
C7 C8 C9 C10 -0.3(3) . . . .
C8 C7 N2 C11 2.0(2) . . . .
C8 C7 P1 C1 -29.99(13) . . . .
C8 C7 P1 C13 -138.30(11) . . . .
C8 C7 P1 O1 95.24(12) . . . .
C8 C9 C10 C11 2.3(3) . . . .
C9 C10 C11 C12 176.23(19) . . . .
C9 C10 C11 N2 -2.3(3) . . . .
C10 C11 N2 C7 0.2(2) . . . .
C12 C11 N2 C7 -178.42(15) . . . .
C13 C14 C15 C16 1.1(2) . . . .
C14 C13 N3 C17 -0.2(2) . . . .
C14 C13 P1 C1 -78.43(12) . . . .
C14 C13 P1 C7 32.08(13) . . . .
C14 C13 P1 O1 158.07(11) . . . .
C14 C15 C16 C17 0.0(2) . . . .
C15 C16 C17 C18 178.24(18) . . . .
C15 C16 C17 N3 -1.3(2) . . . .
C16 C17 N3 C13 1.4(2) . . . .
C18 C17 N3 C13 -178.19(15) . . . .
N1 C1 C2 C3 1.2(2) . . . .
N1 C1 P1 C7 -46.45(11) . . . .
N1 C1 P1 C13 64.45(11) . . . .
N1 C1 P1 O1 -171.61(9) . . . .
N2 C7 C8 C9 -1.9(2) . . . .
N2 C7 P1 C1 154.82(10) . . . .
N2 C7 P1 C13 46.52(11) . . . .
N2 C7 P1 O1 -79.94(11) . . . .
N3 C13 C14 C15 -1.0(2) . . . .
N3 C13 P1 C1 97.35(10) . . . .
N3 C13 P1 C7 -152.14(9) . . . .
N3 C13 P1 O1 -26.15(11) . . . .
P1 C1 C2 C3 177.66(11) . . . .
P1 C1 N1 C5 -177.60(10) . . . .
P1 C7 C8 C9 -176.59(12) . . . .
P1 C7 N2 C11 177.06(10) . . . .
P1 C13 C14 C15 174.36(12) . . . .
P1 C13 N3 C17 -175.95(10) . . . .
