#------------------------------------------------------------------------------
#$Date: 2021-10-14 01:02:12 +0300 (Thu, 14 Oct 2021) $
#$Revision: 269912 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/90/7129085.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_7129085
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 P'
_chemical_formula_weight         453.49
_chemical_name_systematic        PN-TPN
_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                104.06(3)
_cell_angle_beta                 110.34(3)
_cell_angle_gamma                96.49(3)
_cell_formula_units_Z            2
_cell_length_a                   9.4530(19)
_cell_length_b                   10.884(2)
_cell_length_c                   13.043(3)
_cell_measurement_reflns_used    11683
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      1.747
_cell_volume                     1191.5(6)
_computing_cell_refinement       'Rigaku Rapid Auto'
_computing_data_collection       'Rigaku Rapid Auto'
_computing_data_reduction        'Rigaku Rapid Auto'
_computing_molecular_graphics    'Bruker SHELXTL'
_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 0.997
_diffrn_measured_fraction_theta_max 0.995
_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  0.0468
_diffrn_reflns_av_unetI/netI     0.0684
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11683
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         1.747
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Rigaku Rapid Auto'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_description       hexahedron
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.051
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         5444
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0621
_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)+(0.0413P)²+0.8077P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1301
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3920
_reflns_number_total             5444
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc04785j2.cif
_cod_data_source_block           P-1
_cod_original_cell_volume        1191.4(5)
_cod_database_code               7129085
_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   0.964
_shelx_estimated_absorpt_t_max   0.993
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 0.7151(2) -0.05179(18) 0.29279(16) 0.0287(4) Uani 1 1 d . . . . .
P1 P 0.59835(7) 0.05274(6) 0.31540(5) 0.02772(15) Uani 1 1 d . . . . .
C1 C 0.6067(2) 0.1390(2) 0.21326(18) 0.0253(5) Uani 1 1 d . . . . .
C2 C 0.4757(2) 0.2059(2) 0.17879(19) 0.0264(5) Uani 1 1 d . . . . .
C3 C 0.4342(3) 0.2811(2) 0.2623(2) 0.0321(5) Uani 1 1 d . . . . .
H3 H 0.4939 0.2942 0.3411 0.038 Uiso 1 1 calc R U . . .
C4 C 0.3070(3) 0.3369(2) 0.2318(2) 0.0365(6) Uani 1 1 d . . . . .
H4 H 0.2817 0.3896 0.2897 0.044 Uiso 1 1 calc R U . . .
C5 C 0.2172(3) 0.3164(2) 0.1180(2) 0.0364(6) Uani 1 1 d . . . . .
H5 H 0.1288 0.3530 0.0973 0.044 Uiso 1 1 calc R U . . .
C6 C 0.2565(3) 0.2422(2) 0.0342(2) 0.0369(6) Uani 1 1 d . . . . .
H6 H 0.1953 0.2284 -0.0445 0.044 Uiso 1 1 calc R U . . .
C7 C 0.3845(3) 0.1877(2) 0.0643(2) 0.0327(5) Uani 1 1 d . . . . .
H7 H 0.4106 0.1370 0.0059 0.039 Uiso 1 1 calc R U . . .
C8 C 0.7196(2) 0.1393(2) 0.17132(18) 0.0264(5) Uani 1 1 d . . . . .
C9 C 0.7292(2) 0.2225(2) 0.09695(19) 0.0270(5) Uani 1 1 d . . . . .
C10 C 0.7644(3) 0.3563(2) 0.1424(2) 0.0347(5) Uani 1 1 d . . . . .
H10 H 0.7815 0.3947 0.2205 0.042 Uiso 1 1 calc R U . . .
C11 C 0.7749(3) 0.4350(2) 0.0750(2) 0.0429(6) Uani 1 1 d . . . . .
H11 H 0.7989 0.5267 0.1070 0.052 Uiso 1 1 calc R U . . .
C12 C 0.7506(3) 0.3801(3) -0.0383(2) 0.0458(7) Uani 1 1 d . . . . .
H12 H 0.7588 0.4341 -0.0843 0.055 Uiso 1 1 calc R U . . .
C13 C 0.7145(3) 0.2470(3) -0.0852(2) 0.0424(6) Uani 1 1 d . . . . .
H13 H 0.6962 0.2092 -0.1636 0.051 Uiso 1 1 calc R U . . .
C14 C 0.7051(3) 0.1686(2) -0.0177(2) 0.0346(5) Uani 1 1 d . . . . .
H14 H 0.6819 0.0769 -0.0500 0.042 Uiso 1 1 calc R U . . .
C15 C 0.8443(2) 0.0683(2) 0.20295(19) 0.0266(5) Uani 1 1 d . . . . .
C16 C 0.9717(3) 0.0910(2) 0.1724(2) 0.0333(5) Uani 1 1 d . . . . .
H16 H 0.9764 0.1533 0.1332 0.040 Uiso 1 1 calc R U . . .
C17 C 1.0895(3) 0.0256(3) 0.1977(2) 0.0392(6) Uani 1 1 d . . . . .
H17 H 1.1738 0.0425 0.1758 0.047 Uiso 1 1 calc R U . . .
C18 C 1.0843(3) -0.0648(3) 0.2553(2) 0.0379(6) Uani 1 1 d . . . . .
H18 H 1.1651 -0.1105 0.2728 0.045 Uiso 1 1 calc R U . . .
C19 C 0.9615(3) -0.0891(2) 0.2875(2) 0.0326(5) Uani 1 1 d . . . . .
H19 H 0.9592 -0.1511 0.3275 0.039 Uiso 1 1 calc R U . . .
C20 C 0.8413(2) -0.0236(2) 0.26209(19) 0.0270(5) Uani 1 1 d . . . . .
C21 C 0.7004(3) -0.1632(2) 0.3325(2) 0.0298(5) Uani 1 1 d . . . . .
C22 C 0.6389(3) -0.2854(2) 0.2540(2) 0.0361(6) Uani 1 1 d . . . . .
H22 H 0.6089 -0.2961 0.1744 0.043 Uiso 1 1 calc R U . . .
C23 C 0.6208(3) -0.3927(3) 0.2917(3) 0.0435(7) Uani 1 1 d . . . . .
H23 H 0.5774 -0.4768 0.2378 0.052 Uiso 1 1 calc R U . . .
C24 C 0.6660(3) -0.3773(3) 0.4076(3) 0.0488(7) Uani 1 1 d . . . . .
H24 H 0.6534 -0.4508 0.4333 0.059 Uiso 1 1 calc R U . . .
C25 C 0.7290(3) -0.2560(3) 0.4856(3) 0.0474(7) Uani 1 1 d . . . . .
H25 H 0.7607 -0.2458 0.5653 0.057 Uiso 1 1 calc R U . . .
C26 C 0.7466(3) -0.1482(3) 0.4486(2) 0.0370(6) Uani 1 1 d . . . . .
H26 H 0.7902 -0.0643 0.5028 0.044 Uiso 1 1 calc R U . . .
C27 C 0.7154(3) 0.1833(2) 0.44995(19) 0.0300(5) Uani 1 1 d . . . . .
C28 C 0.8545(3) 0.2626(3) 0.4714(2) 0.0395(6) Uani 1 1 d . . . . .
H28 H 0.8993 0.2473 0.4159 0.047 Uiso 1 1 calc R U . . .
C29 C 0.9289(3) 0.3633(3) 0.5721(2) 0.0492(7) Uani 1 1 d . . . . .
H29 H 1.0251 0.4157 0.5860 0.059 Uiso 1 1 calc R U . . .
C30 C 0.8638(3) 0.3882(3) 0.6529(2) 0.0498(7) Uani 1 1 d . . . . .
H30 H 0.9139 0.4585 0.7215 0.060 Uiso 1 1 calc R U . . .
C31 C 0.7263(4) 0.3106(3) 0.6332(2) 0.0477(7) Uani 1 1 d . . . . .
H31 H 0.6811 0.3274 0.6884 0.057 Uiso 1 1 calc R U . . .
C32 C 0.6530(3) 0.2080(3) 0.5333(2) 0.0387(6) Uani 1 1 d . . . . .
H32 H 0.5591 0.1538 0.5214 0.046 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'
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
C20 N1 C21 118.41(18) . . ?
C20 N1 P1 125.02(15) . . ?
C21 N1 P1 115.16(14) . . ?
N1 P1 C1 98.77(9) . . ?
N1 P1 C27 106.90(10) . . ?
C1 P1 C27 98.93(10) . . ?
C8 C1 C2 123.80(19) . . ?
C8 C1 P1 122.70(16) . . ?
C2 C1 P1 113.49(15) . . ?
C7 C2 C3 117.9(2) . . ?
C7 C2 C1 122.0(2) . . ?
C3 C2 C1 119.9(2) . . ?
C4 C3 C2 120.9(2) . . ?
C5 C4 C3 120.3(2) . . ?
C4 C5 C6 119.6(2) . . ?
C5 C6 C7 120.2(2) . . ?
C6 C7 C2 121.1(2) . . ?
C1 C8 C15 122.9(2) . . ?
C1 C8 C9 120.12(19) . . ?
C15 C8 C9 116.75(18) . . ?
C10 C9 C14 118.6(2) . . ?
C10 C9 C8 119.9(2) . . ?
C14 C9 C8 121.5(2) . . ?
C9 C10 C11 120.7(2) . . ?
C12 C11 C10 120.0(2) . . ?
C11 C12 C13 120.1(2) . . ?
C12 C13 C14 119.9(2) . . ?
C13 C14 C9 120.7(2) . . ?
C20 C15 C16 117.7(2) . . ?
C20 C15 C8 122.70(19) . . ?
C16 C15 C8 119.6(2) . . ?
C17 C16 C15 122.0(2) . . ?
C16 C17 C18 119.5(2) . . ?
C17 C18 C19 120.2(2) . . ?
C18 C19 C20 120.8(2) . . ?
C19 C20 C15 119.83(19) . . ?
C19 C20 N1 120.2(2) . . ?
C15 C20 N1 119.98(19) . . ?
C22 C21 C26 119.9(2) . . ?
C22 C21 N1 119.7(2) . . ?
C26 C21 N1 120.4(2) . . ?
C21 C22 C23 119.9(2) . . ?
C24 C23 C22 120.0(3) . . ?
C25 C24 C23 120.0(2) . . ?
C24 C25 C26 120.3(3) . . ?
C21 C26 C25 119.8(3) . . ?
C28 C27 C32 118.0(2) . . ?
C28 C27 P1 125.31(18) . . ?
C32 C27 P1 116.54(19) . . ?
C29 C28 C27 121.1(2) . . ?
C28 C29 C30 120.2(3) . . ?
C31 C30 C29 119.6(3) . . ?
C30 C31 C32 120.4(2) . . ?
C31 C32 C27 120.8(3) . . ?
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 C20 1.410(3) . ?
N1 C21 1.440(3) . ?
N1 P1 1.7163(19) . ?
P1 C1 1.823(2) . ?
P1 C27 1.846(3) . ?
C1 C8 1.359(3) . ?
C1 C2 1.497(3) . ?
C2 C7 1.391(3) . ?
C2 C3 1.395(3) . ?
C3 C4 1.387(3) . ?
C4 C5 1.375(4) . ?
C5 C6 1.381(4) . ?
C6 C7 1.384(3) . ?
C8 C15 1.476(3) . ?
C8 C9 1.496(3) . ?
C9 C10 1.385(3) . ?
C9 C14 1.393(3) . ?
C10 C11 1.386(3) . ?
C11 C12 1.378(4) . ?
C12 C13 1.380(4) . ?
C13 C14 1.383(3) . ?
C15 C20 1.408(3) . ?
C15 C16 1.408(3) . ?
C16 C17 1.376(3) . ?
C17 C18 1.382(3) . ?
C18 C19 1.384(3) . ?
C19 C20 1.395(3) . ?
C21 C22 1.380(3) . ?
C21 C26 1.383(3) . ?
C22 C23 1.388(3) . ?
C23 C24 1.380(4) . ?
C24 C25 1.371(4) . ?
C25 C26 1.387(3) . ?
C27 C28 1.386(3) . ?
C27 C32 1.394(3) . ?
C28 C29 1.381(4) . ?
C29 C30 1.382(4) . ?
C30 C31 1.372(4) . ?
C31 C32 1.384(4) . ?
