#------------------------------------------------------------------------------
#$Date: 2020-10-07 01:57:45 +0300 (Wed, 07 Oct 2020) $
#$Revision: 258199 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/81/4038140.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_4038140
loop_
_publ_author_name
'Rahman, Md Shafiqur'
'Yoshikai, Naohiko'
_publ_section_title
;
 Synthesis of triphenylene-fused phosphole oxides via C--H
 functionalizations
;
_journal_name_full               'Beilstein Journal of Organic Chemistry'
_journal_page_first              524
_journal_page_last               529
_journal_paper_doi               10.3762/bjoc.16.48
_journal_volume                  16
_journal_year                    2020
_chemical_formula_sum            'C36 H37 O3 P'
_chemical_formula_weight         548.62
_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                 90.8293(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5972(2)
_cell_length_b                   23.8844(6)
_cell_length_c                   15.6911(3)
_cell_measurement_reflns_used    7947
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      28.2027
_cell_measurement_theta_min      2.5964
_cell_volume                     2846.92(12)
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_collection       'APEX3 (Bruker AXS Inc., 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2016)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'XS, VERSION 2013/1'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 7.4074
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Multilayer Mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0725
_diffrn_reflns_av_unetI/netI     0.0599
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            36188
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.73
_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_type   'Numerical Mu Calculated'
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.221
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.154
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.372
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         7026
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0521
_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)+(0.0324P)²+1.9886P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1137
_reflns_number_gt                5336
_reflns_number_total             7026
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            1860-5397-16-48-S2.cif
_cod_data_source_block           yoshi60m
_cod_depositor_comments          'Adding full bibliography for 4038140.cif.'
_cod_database_code               4038140
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_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_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.5817(2) 0.19683(7) 0.23245(11) 0.0132(4) Uani d . . . 1 . .
C C2 0.5374(2) 0.17979(7) 0.31094(11) 0.0126(4) Uani d . . . 1 . .
C C3 0.5589(2) 0.22295(7) 0.37861(11) 0.0122(4) Uani d . . . 1 . .
C C4 0.5176(2) 0.21401(8) 0.46366(11) 0.0147(4) Uani d . . . 1 . .
H H4 0.4744 0.1786 0.4814 0.018 Uiso calc U . R 1 . .
C C5 0.5394(2) 0.25649(7) 0.52191(11) 0.0143(4) Uani d . . . 1 . .
H H5 0.511 0.2499 0.5798 0.017 Uiso calc U . R 1 . .
C C6 0.6025(2) 0.30940(7) 0.49816(11) 0.0123(3) Uani d . . . 1 . .
C C7 0.6156(2) 0.35401(7) 0.56217(11) 0.0135(4) Uani d . . . 1 . .
C C8 0.5838(2) 0.34327(8) 0.64955(11) 0.0151(4) Uani d . . . 1 . .
H H8 0.5608 0.306 0.6674 0.018 Uiso calc U . R 1 . .
C C9 0.5854(2) 0.38552(8) 0.70873(11) 0.0152(4) Uani d . . . 1 . .
C C10 0.6159(3) 0.44138(8) 0.68234(11) 0.0170(4) Uani d . . . 1 . .
C C11 0.6518(3) 0.45207(8) 0.59852(11) 0.0163(4) Uani d . . . 1 . .
H H11 0.6749 0.4895 0.5813 0.02 Uiso calc U . R 1 . .
C C12 0.6552(2) 0.40873(7) 0.53715(11) 0.0146(4) Uani d . . . 1 . .
C C13 0.7087(2) 0.41969(7) 0.44962(11) 0.0148(4) Uani d . . . 1 . .
C C14 0.7679(3) 0.47317(8) 0.42475(12) 0.0208(4) Uani d . . . 1 . .
H H14 0.7608 0.5033 0.464 0.025 Uiso calc U . R 1 . .
C C15 0.8357(3) 0.48291(8) 0.34529(12) 0.0228(4) Uani d . . . 1 . .
H H15 0.8729 0.5194 0.3297 0.027 Uiso calc U . R 1 . .
C C16 0.8492(3) 0.43869(8) 0.28807(12) 0.0202(4) Uani d . . . 1 . .
H H16 0.8996 0.4447 0.2338 0.024 Uiso calc U . R 1 . .
C C17 0.7898(2) 0.38632(8) 0.31002(11) 0.0155(4) Uani d . . . 1 . .
H H17 0.8001 0.3566 0.2702 0.019 Uiso calc U . R 1 . .
C C18 0.7142(2) 0.37535(7) 0.38956(11) 0.0135(4) Uani d . . . 1 . .
C C19 0.6477(2) 0.31958(7) 0.41168(11) 0.0118(3) Uani d . . . 1 . .
C C20 0.6247(2) 0.27482(7) 0.35230(10) 0.0118(3) Uani d . . . 1 . .
C C21 0.5002(2) 0.31167(7) 0.18225(10) 0.0132(4) Uani d . . . 1 . .
C C22 0.3220(2) 0.31045(7) 0.20206(11) 0.0149(4) Uani d . . . 1 . .
H H22 0.2821 0.2866 0.2463 0.018 Uiso calc U . R 1 . .
C C23 0.2028(3) 0.34372(8) 0.15777(11) 0.0167(4) Uani d . . . 1 . .
H H23 0.0816 0.3429 0.1718 0.02 Uiso calc U . R 1 . .
C C24 0.2608(3) 0.37835(8) 0.09272(11) 0.0180(4) Uani d . . . 1 . .
H H24 0.1792 0.4014 0.0627 0.022 Uiso calc U . R 1 . .
C C25 0.4373(3) 0.37929(8) 0.07157(11) 0.0192(4) Uani d . . . 1 . .
H H25 0.4763 0.4026 0.0266 0.023 Uiso calc U . R 1 . .
C C26 0.5571(3) 0.34605(8) 0.11629(11) 0.0167(4) Uani d . . . 1 . .
H H26 0.6781 0.3467 0.1019 0.02 Uiso calc U . R 1 . .
C C27 0.5909(3) 0.16020(8) 0.15429(11) 0.0161(4) Uani d . . . 1 . .
H H27A 0.4878 0.1349 0.1541 0.019 Uiso calc U . R 1 . .
H H27B 0.6975 0.1365 0.1595 0.019 Uiso calc U . R 1 . .
C C28 0.5954(3) 0.19008(8) 0.06841(11) 0.0169(4) Uani d . . . 1 . .
H H28A 0.6876 0.2194 0.07 0.02 Uiso calc U . R 1 . .
H H28B 0.4807 0.2086 0.0573 0.02 Uiso calc U . R 1 . .
C C29 0.6334(3) 0.14895(8) -0.00342(11) 0.0196(4) Uani d . . . 1 . .
H H29A 0.7452 0.1292 0.0094 0.024 Uiso calc U . R 1 . .
H H29B 0.5383 0.1206 -0.0062 0.024 Uiso calc U . R 1 . .
C C30 0.6468(3) 0.17778(9) -0.08975(11) 0.0251(5) Uani d . . . 1 . .
H H30A 0.5351 0.1964 -0.1036 0.038 Uiso calc U . R 1 . .
H H30B 0.6724 0.1499 -0.1336 0.038 Uiso calc U . R 1 . .
H H30C 0.7416 0.2056 -0.0875 0.038 Uiso calc U . R 1 . .
C C31 0.4854(2) 0.12107(7) 0.33338(11) 0.0141(4) Uani d . . . 1 . .
H H31A 0.4297 0.103 0.283 0.017 Uiso calc U . R 1 . .
H H31B 0.3979 0.122 0.3795 0.017 Uiso calc U . R 1 . .
C C32 0.6453(2) 0.08655(7) 0.36260(11) 0.0153(4) Uani d . . . 1 . .
H H32A 0.7241 0.0808 0.3137 0.018 Uiso calc U . R 1 . .
H H32B 0.7117 0.1077 0.4068 0.018 Uiso calc U . R 1 . .
C C33 0.5925(3) 0.03006(8) 0.39841(12) 0.0200(4) Uani d . . . 1 . .
H H33A 0.5183 0.0102 0.3557 0.024 Uiso calc U . R 1 . .
H H33B 0.5211 0.036 0.4499 0.024 Uiso calc U . R 1 . .
C C34 0.7507(3) -0.00655(9) 0.42163(14) 0.0276(5) Uani d . . . 1 . .
H H34A 0.8284 -0.0094 0.3725 0.041 Uiso calc U . R 1 . .
H H34B 0.71 -0.044 0.4376 0.041 Uiso calc U . R 1 . .
H H34C 0.8153 0.0102 0.4697 0.041 Uiso calc U . R 1 . .
C C35 0.5511(3) 0.32330(8) 0.82624(12) 0.0203(4) Uani d . . . 1 . .
H H35A 0.4523 0.3034 0.7993 0.03 Uiso calc U . R 1 . .
H H35B 0.535 0.3243 0.8881 0.03 Uiso calc U . R 1 . .
H H35C 0.6614 0.3039 0.8135 0.03 Uiso calc U . R 1 . .
C C36 0.6352(3) 0.53749(8) 0.72013(13) 0.0250(5) Uani d . . . 1 . .
H H36A 0.7552 0.5419 0.699 0.038 Uiso calc U . R 1 . .
H H36B 0.6183 0.5621 0.7693 0.038 Uiso calc U . R 1 . .
H H36C 0.5505 0.5474 0.6749 0.038 Uiso calc U . R 1 . .
O O1 0.84011(17) 0.27614(5) 0.20393(8) 0.0156(3) Uani d . . . 1 . .
O O2 0.55811(18) 0.37921(5) 0.79401(8) 0.0190(3) Uani d . . . 1 . .
O O3 0.60813(19) 0.48057(5) 0.74520(8) 0.0228(3) Uani d . . . 1 . .
P P1 0.65873(6) 0.26798(2) 0.23732(3) 0.01201(11) Uani d . . . 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C27 . . 125.73(16) ?
C2 C1 P1 . . 109.43(13) ?
C27 C1 P1 . . 124.31(13) ?
C1 C2 C3 . . 114.70(16) ?
C1 C2 C31 . . 124.63(16) ?
C3 C2 C31 . . 120.45(15) ?
C4 C3 C20 . . 120.32(16) ?
C4 C3 C2 . . 123.66(16) ?
C20 C3 C2 . . 116.01(15) ?
C5 C4 C3 . . 119.85(17) ?
C4 C5 C6 . . 121.77(16) ?
C5 C6 C19 . . 119.61(15) ?
C5 C6 C7 . . 119.49(16) ?
C19 C6 C7 . . 120.87(16) ?
C12 C7 C8 . . 118.72(16) ?
C12 C7 C6 . . 119.96(16) ?
C8 C7 C6 . . 121.29(16) ?
C9 C8 C7 . . 121.42(17) ?
O2 C9 C8 . . 125.62(17) ?
O2 C9 C10 . . 114.72(15) ?
C8 C9 C10 . . 119.66(16) ?
O3 C10 C11 . . 125.31(17) ?
O3 C10 C9 . . 115.25(16) ?
C11 C10 C9 . . 119.43(16) ?
C10 C11 C12 . . 121.51(17) ?
C7 C12 C11 . . 119.12(16) ?
C7 C12 C13 . . 119.67(16) ?
C11 C12 C13 . . 121.13(16) ?
C14 C13 C18 . . 118.63(17) ?
C14 C13 C12 . . 121.07(16) ?
C18 C13 C12 . . 120.13(16) ?
C15 C14 C13 . . 121.92(18) ?
C14 C15 C16 . . 119.26(18) ?
C17 C16 C15 . . 120.08(18) ?
C16 C17 C18 . . 122.11(17) ?
C17 C18 C13 . . 117.85(16) ?
C17 C18 C19 . . 121.69(16) ?
C13 C18 C19 . . 120.44(16) ?
C6 C19 C20 . . 117.70(15) ?
C6 C19 C18 . . 117.92(15) ?
C20 C19 C18 . . 124.38(15) ?
C3 C20 C19 . . 120.73(15) ?
C3 C20 P1 . . 105.51(12) ?
C19 C20 P1 . . 133.74(13) ?
C22 C21 C26 . . 119.37(16) ?
C22 C21 P1 . . 121.65(13) ?
C26 C21 P1 . . 118.94(14) ?
C23 C22 C21 . . 120.44(17) ?
C22 C23 C24 . . 119.87(18) ?
C25 C24 C23 . . 120.22(17) ?
C24 C25 C26 . . 119.90(17) ?
C25 C26 C21 . . 120.20(18) ?
C1 C27 C28 . . 116.65(15) ?
C27 C28 C29 . . 111.00(15) ?
C30 C29 C28 . . 112.43(17) ?
C2 C31 C32 . . 111.25(15) ?
C33 C32 C31 . . 112.11(15) ?
C32 C33 C34 . . 112.73(17) ?
C9 O2 C35 . . 117.18(14) ?
C10 O3 C36 . . 116.49(15) ?
O1 P1 C1 . . 114.18(8) ?
O1 P1 C21 . . 111.66(8) ?
C1 P1 C21 . . 108.15(8) ?
O1 P1 C20 . . 118.52(8) ?
C1 P1 C20 . . 94.33(8) ?
C21 P1 C20 . . 108.48(8) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.345(2) ?
C1 C27 . 1.509(2) ?
C1 P1 . 1.7984(18) ?
C2 C3 . 1.487(2) ?
C2 C31 . 1.500(2) ?
C3 C4 . 1.392(2) ?
C3 C20 . 1.400(2) ?
C4 C5 . 1.374(2) ?
C5 C6 . 1.404(2) ?
C6 C19 . 1.425(2) ?
C6 C7 . 1.467(2) ?
C7 C12 . 1.399(3) ?
C7 C8 . 1.419(2) ?
C8 C9 . 1.371(2) ?
C9 O2 . 1.365(2) ?
C9 C10 . 1.417(3) ?
C10 O3 . 1.362(2) ?
C10 C11 . 1.371(3) ?
C11 C12 . 1.414(2) ?
C12 C13 . 1.461(2) ?
C13 C14 . 1.411(3) ?
C13 C18 . 1.419(2) ?
C14 C15 . 1.376(3) ?
C15 C16 . 1.391(3) ?
C16 C17 . 1.375(3) ?
C17 C18 . 1.406(2) ?
C18 C19 . 1.468(2) ?
C19 C20 . 1.427(2) ?
C20 P1 . 1.8336(17) ?
C21 C22 . 1.393(3) ?
C21 C26 . 1.395(2) ?
C21 P1 . 1.8046(18) ?
C22 C23 . 1.384(3) ?
C23 C24 . 1.390(3) ?
C24 C25 . 1.386(3) ?
C25 C26 . 1.390(3) ?
C27 C28 . 1.526(2) ?
C28 C29 . 1.526(3) ?
C29 C30 . 1.524(3) ?
C31 C32 . 1.533(2) ?
C32 C33 . 1.518(2) ?
C33 C34 . 1.526(3) ?
C35 O2 . 1.429(2) ?
C36 O3 . 1.431(2) ?
O1 P1 . 1.4941(14) ?
