#------------------------------------------------------------------------------
#$Date: 2021-10-14 01:02:12 +0300 (Thu, 14 Oct 2021) $
#$Revision: 269912 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/90/7129086.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_7129086
loop_
_publ_author_name
'Park, Jupil'
'Kim, So Jung'
'Kwon, Hansol'
'Jin, Eunji'
'Yoon, Kihwan'
'Kim, HyunHo'
'Shadman, Sahar'
'Choe, Wonyoung'
'Kim, Joonghan'
'Park, Young S.'
_publ_section_title
;
 PN-doped tetraphenylnaphthalene: A straightforward synthetic strategy
 analogous to BN-annulation
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC04785J
_journal_year                    2021
_chemical_formula_sum            'C32 H24 N O P'
_chemical_formula_weight         469.49
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-08-31 deposited with the CCDC.	2021-10-08 downloaded from the CCDC.
;
_cell_angle_alpha                69.43(3)
_cell_angle_beta                 86.51(3)
_cell_angle_gamma                71.10(3)
_cell_formula_units_Z            2
_cell_length_a                   10.347(2)
_cell_length_b                   11.030(2)
_cell_length_c                   11.987(2)
_cell_measurement_reflns_used    11934
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      0.998
_cell_measurement_theta_min      0.998
_cell_volume                     1209.6(5)
_computing_cell_refinement       'Rigaku Rapid Auto'
_computing_data_collection       'Rigaku Rapid Auto'
_computing_data_reduction        'Rigaku Rapid Auto'
_computing_publication_material  CIFTAB
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    SHELXS
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'imaging plate'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11934
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         2.084
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Rigaku Rapid Auto'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_description       hexahedron
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.271
_exptl_crystal_size_mid          0.113
_exptl_crystal_size_min          0.099
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         5544
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0477
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0294P)²+0.7245P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.1009
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4291
_reflns_number_total             5544
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc04785j2.cif
_cod_data_source_block           P-1_CCDC1
_cod_database_code               7129086
_shelx_shelxl_version_number     2014/7
_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_min   0.963
_shelx_estimated_absorpt_t_max   0.986
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
N1 N 0.77517(15) 0.54033(15) 0.08726(13) 0.0204(3) Uani 1 1 d . . . . .
O1 O 0.65705(12) 0.57310(12) 0.28371(11) 0.0237(3) Uani 1 1 d . . . . .
P1 P 0.74876(4) 0.47399(5) 0.23372(4) 0.01727(11) Uani 1 1 d . . . . .
C1 C 0.69353(16) 0.34330(17) 0.21150(16) 0.0179(3) Uani 1 1 d . . . . .
C2 C 0.67664(16) 0.37676(17) 0.08190(15) 0.0181(3) Uani 1 1 d . . . . .
C3 C 0.62095(17) 0.31724(18) 0.01977(16) 0.0213(4) Uani 1 1 d . . . . .
H3 H 0.5876 0.2440 0.0627 0.026 Uiso 1 1 calc R U . . .
C4 C 0.61399(18) 0.36407(19) -0.10367(17) 0.0251(4) Uani 1 1 d . . . . .
H4 H 0.5765 0.3228 -0.1451 0.030 Uiso 1 1 calc R U . . .
C5 C 0.66191(18) 0.4717(2) -0.16697(17) 0.0263(4) Uani 1 1 d . . . . .
H5 H 0.6585 0.5021 -0.2517 0.032 Uiso 1 1 calc R U . . .
C6 C 0.71445(18) 0.53509(19) -0.10835(16) 0.0231(4) Uani 1 1 d . . . . .
H6 H 0.7451 0.6099 -0.1522 0.028 Uiso 1 1 calc R U . . .
C7 C 0.72161(16) 0.48743(18) 0.01554(15) 0.0189(4) Uani 1 1 d . . . . .
C8 C 0.81115(18) 0.66309(18) 0.03979(16) 0.0209(4) Uani 1 1 d . . . . .
C9 C 0.7166(2) 0.7863(2) -0.02829(18) 0.0287(4) Uani 1 1 d . . . . .
H9 H 0.6263 0.7903 -0.0445 0.034 Uiso 1 1 calc R U . . .
C10 C 0.7542(2) 0.9035(2) -0.07251(19) 0.0334(5) Uani 1 1 d . . . . .
H10 H 0.6897 0.9876 -0.1198 0.040 Uiso 1 1 calc R U . . .
C11 C 0.8853(2) 0.8984(2) -0.04798(18) 0.0308(4) Uani 1 1 d . . . . .
H11 H 0.9107 0.9789 -0.0784 0.037 Uiso 1 1 calc R U . . .
C12 C 0.97883(19) 0.7765(2) 0.02065(18) 0.0284(4) Uani 1 1 d . . . . .
H12 H 1.0685 0.7732 0.0380 0.034 Uiso 1 1 calc R U . . .
C13 C 0.94224(18) 0.65864(19) 0.06442(17) 0.0247(4) Uani 1 1 d . . . . .
H13 H 1.0071 0.5746 0.1114 0.030 Uiso 1 1 calc R U . . .
C14 C 0.91303(17) 0.38872(17) 0.31380(15) 0.0187(3) Uani 1 1 d . . . . .
C15 C 1.01938(18) 0.30196(18) 0.27276(16) 0.0236(4) Uani 1 1 d . . . . .
H15 H 1.0074 0.2928 0.1985 0.028 Uiso 1 1 calc R U . . .
C16 C 1.14180(19) 0.2296(2) 0.33974(18) 0.0288(4) Uani 1 1 d . . . . .
H16 H 1.2143 0.1713 0.3112 0.035 Uiso 1 1 calc R U . . .
C17 C 1.1590(2) 0.2418(2) 0.44873(19) 0.0326(5) Uani 1 1 d . . . . .
H17 H 1.2432 0.1915 0.4949 0.039 Uiso 1 1 calc R U . . .
C18 C 1.0542(2) 0.3268(2) 0.49032(18) 0.0325(5) Uani 1 1 d . . . . .
H18 H 1.0663 0.3345 0.5652 0.039 Uiso 1 1 calc R U . . .
C19 C 0.93109(19) 0.4010(2) 0.42288(17) 0.0260(4) Uani 1 1 d . . . . .
H19 H 0.8593 0.4600 0.4513 0.031 Uiso 1 1 calc R U . . .
C20 C 0.68425(16) 0.23375(17) 0.30363(15) 0.0174(3) Uani 1 1 d . . . . .
C21 C 0.70431(17) 0.22267(17) 0.42977(15) 0.0184(3) Uani 1 1 d . . . . .
C22 C 0.81389(18) 0.11663(18) 0.50197(16) 0.0230(4) Uani 1 1 d . . . . .
H22 H 0.8712 0.0496 0.4721 0.028 Uiso 1 1 calc R U . . .
C23 C 0.8393(2) 0.1088(2) 0.61642(17) 0.0276(4) Uani 1 1 d . . . . .
H23 H 0.9161 0.0385 0.6639 0.033 Uiso 1 1 calc R U . . .
C24 C 0.7530(2) 0.2033(2) 0.66253(17) 0.0283(4) Uani 1 1 d . . . . .
H24 H 0.7713 0.1981 0.7411 0.034 Uiso 1 1 calc R U . . .
C25 C 0.6407(2) 0.30464(19) 0.59394(17) 0.0268(4) Uani 1 1 d . . . . .
H25 H 0.5796 0.3672 0.6264 0.032 Uiso 1 1 calc R U . . .
C26 C 0.61691(18) 0.31525(18) 0.47757(16) 0.0229(4) Uani 1 1 d . . . . .
H26 H 0.5404 0.3862 0.4302 0.027 Uiso 1 1 calc R U . . .
C27 C 0.65796(17) 0.11344(17) 0.29140(15) 0.0194(4) Uani 1 1 d . . . . .
C28 C 0.54253(18) 0.08074(18) 0.33876(17) 0.0233(4) Uani 1 1 d . . . . .
H28 H 0.4808 0.1360 0.3773 0.028 Uiso 1 1 calc R U . . .
C29 C 0.5162(2) -0.0315(2) 0.33060(18) 0.0285(4) Uani 1 1 d . . . . .
H29 H 0.4356 -0.0513 0.3614 0.034 Uiso 1 1 calc R U . . .
C30 C 0.6076(2) -0.1148(2) 0.27740(18) 0.0304(4) Uani 1 1 d . . . . .
H30 H 0.5904 -0.1922 0.2722 0.036 Uiso 1 1 calc R U . . .
C31 C 0.7239(2) -0.0846(2) 0.23196(18) 0.0305(4) Uani 1 1 d . . . . .
H31 H 0.7870 -0.1420 0.1960 0.037 Uiso 1 1 calc R U . . .
C32 C 0.74957(19) 0.02904(19) 0.23837(17) 0.0253(4) Uani 1 1 d . . . . .
H32 H 0.8297 0.0491 0.2065 0.030 Uiso 1 1 calc R U . . .
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
_geom_angle_publ_flag
C7 N1 C8 123.24(15) . . ?
C7 N1 P1 112.89(12) . . ?
C8 N1 P1 121.55(12) . . ?
O1 P1 N1 114.86(8) . . ?
O1 P1 C14 112.14(8) . . ?
N1 P1 C14 107.80(8) . . ?
O1 P1 C1 120.62(8) . . ?
N1 P1 C1 92.41(8) . . ?
C14 P1 C1 106.94(8) . . ?
C20 C1 C2 130.50(16) . . ?
C20 C1 P1 121.78(14) . . ?
C2 C1 P1 107.50(12) . . ?
C3 C2 C7 118.28(16) . . ?
C3 C2 C1 129.39(16) . . ?
C7 C2 C1 112.31(15) . . ?
C4 C3 C2 120.57(17) . . ?
C3 C4 C5 119.94(17) . . ?
C6 C5 C4 120.97(17) . . ?
C5 C6 C7 118.86(17) . . ?
C6 C7 C2 121.35(16) . . ?
C6 C7 N1 125.09(16) . . ?
C2 C7 N1 113.55(15) . . ?
C13 C8 C9 119.62(17) . . ?
C13 C8 N1 119.17(16) . . ?
C9 C8 N1 121.20(16) . . ?
C10 C9 C8 119.91(18) . . ?
C11 C10 C9 120.24(19) . . ?
C12 C11 C10 119.96(18) . . ?
C11 C12 C13 120.09(18) . . ?
C12 C13 C8 120.17(18) . . ?
C19 C14 C15 119.53(17) . . ?
C19 C14 P1 119.33(14) . . ?
C15 C14 P1 120.94(14) . . ?
C16 C15 C14 120.21(18) . . ?
C15 C16 C17 119.99(18) . . ?
C18 C17 C16 120.22(18) . . ?
C17 C18 C19 120.12(19) . . ?
C18 C19 C14 119.93(18) . . ?
C1 C20 C27 124.70(16) . . ?
C1 C20 C21 120.96(15) . . ?
C27 C20 C21 114.31(14) . . ?
C26 C21 C22 118.87(17) . . ?
C26 C21 C20 121.89(16) . . ?
C22 C21 C20 119.23(15) . . ?
C23 C22 C21 120.34(17) . . ?
C22 C23 C24 120.28(18) . . ?
C25 C24 C23 119.85(18) . . ?
C24 C25 C26 120.05(17) . . ?
C25 C26 C21 120.50(17) . . ?
C28 C27 C32 118.85(16) . . ?
C28 C27 C20 119.45(15) . . ?
C32 C27 C20 121.64(16) . . ?
C29 C28 C27 120.93(17) . . ?
C30 C29 C28 119.88(18) . . ?
C31 C30 C29 119.63(18) . . ?
C30 C31 C32 120.62(17) . . ?
C31 C32 C27 120.07(17) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C7 1.417(2) . ?
N1 C8 1.434(2) . ?
N1 P1 1.6914(16) . ?
O1 P1 1.4743(13) . ?
P1 C14 1.7955(19) . ?
P1 C1 1.8158(17) . ?
C1 C20 1.347(2) . ?
C1 C2 1.473(2) . ?
C2 C3 1.399(2) . ?
C2 C7 1.407(2) . ?
C3 C4 1.383(3) . ?
C4 C5 1.390(3) . ?
C5 C6 1.385(3) . ?
C6 C7 1.388(2) . ?
C8 C13 1.387(2) . ?
C8 C9 1.388(3) . ?
C9 C10 1.386(3) . ?
C10 C11 1.385(3) . ?
C11 C12 1.378(3) . ?
C12 C13 1.387(3) . ?
C14 C19 1.390(3) . ?
C14 C15 1.397(3) . ?
C15 C16 1.380(3) . ?
C16 C17 1.387(3) . ?
C17 C18 1.381(3) . ?
C18 C19 1.390(3) . ?
C20 C27 1.494(2) . ?
C20 C21 1.495(2) . ?
C21 C26 1.392(2) . ?
C21 C22 1.397(3) . ?
C22 C23 1.380(3) . ?
C23 C24 1.389(3) . ?
C24 C25 1.380(3) . ?
C25 C26 1.389(3) . ?
C27 C28 1.390(2) . ?
C27 C32 1.393(3) . ?
C28 C29 1.387(3) . ?
C29 C30 1.386(3) . ?
C30 C31 1.382(3) . ?
C31 C32 1.390(3) . ?
