#------------------------------------------------------------------------------
#$Date: 2022-10-08 00:56:24 +0300 (Sat, 08 Oct 2022) $
#$Revision: 278491 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/08/7130830.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_7130830
loop_
_publ_author_name
'Ma, Zetong'
'Liu, Yujian'
'Wang, Z.-H.'
'Jiang, Wei'
_publ_section_title
;
 One-pot heteroannulation toward phosphaperylene diimides with high
 luminescence and out-of-plane anisotropy
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC04784E
_journal_year                    2022
_chemical_formula_sum            'C38 H15 F14 N2 O5 P'
_chemical_formula_weight         876.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-08-30 deposited with the CCDC.	2022-10-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.936(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.4624(4)
_cell_length_b                   9.90830(10)
_cell_length_c                   19.9540(3)
_cell_measurement_reflns_used    12518
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.3980
_cell_measurement_theta_min      2.6500
_cell_volume                     3302.76(10)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            35243
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.531
_diffrn_reflns_theta_min         2.645
_exptl_absorpt_coefficient_mu    1.955
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77444
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.763
_exptl_crystal_description       block
_exptl_crystal_F_000             1752
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     541
_refine_ls_number_reflns         6695
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0479
_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)+(0.0754P)²+1.5805P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1292
_refine_ls_wR_factor_ref         0.1401
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5304
_reflns_number_total             6695
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc04784e2.cif
_cod_data_source_block           tx75
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7130830
_shelx_shelxl_version_number     2018/3
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
P1 P 0.57141(3) 0.18276(6) 0.74402(2) 0.03251(14) Uani 1 1 d . . . . .
O60 O 0.53213(9) 0.23335(16) 0.79554(7) 0.0383(3) Uani 1 1 d . . . . .
F34 F 0.92907(10) 0.58322(15) 0.70623(10) 0.0638(4) Uani 1 1 d . . . . .
F56 F 0.14038(9) -0.09666(18) 0.53789(9) 0.0632(4) Uani 1 1 d . . . . .
F57 F 0.11810(10) -0.07230(17) 0.42627(9) 0.0649(4) Uani 1 1 d . . . . .
F35 F 0.93219(11) 0.66343(19) 0.60675(9) 0.0680(5) Uani 1 1 d . . . . .
F33 F 0.98372(11) 0.90662(17) 0.67028(11) 0.0722(5) Uani 1 1 d . . . . .
O58 O 0.30471(10) -0.14647(19) 0.61448(8) 0.0488(4) Uani 1 1 d . . . . .
O36 O 0.78777(11) 0.61435(18) 0.74970(9) 0.0507(4) Uani 1 1 d . . . . .
O59 O 0.26526(11) -0.0947(2) 0.38030(8) 0.0567(5) Uani 1 1 d . . . . .
F32 F 0.97902(12) 0.8239(2) 0.76934(9) 0.0756(5) Uani 1 1 d . . . . .
F55 F 0.09375(11) -0.35556(19) 0.52175(10) 0.0786(6) Uani 1 1 d . . . . .
O37 O 0.75592(12) 0.7197(2) 0.52120(10) 0.0571(5) Uani 1 1 d . . . . .
N46 N 0.28360(11) -0.1168(2) 0.49760(9) 0.0405(4) Uani 1 1 d . . . . .
F54 F 0.07764(12) -0.3438(2) 0.40989(11) 0.0826(6) Uani 1 1 d . . . . .
F53 F -0.01842(11) -0.1527(2) 0.50841(12) 0.0846(6) Uani 1 1 d . . . . .
F51 F -0.03724(11) -0.1547(3) 0.39697(11) 0.0893(6) Uani 1 1 d . . . . .
N23 N 0.77661(12) 0.6584(2) 0.63539(10) 0.0431(4) Uani 1 1 d . . . . .
F31 F 1.08694(12) 0.6285(2) 0.75576(15) 0.1040(8) Uani 1 1 d . . . . .
F29 F 1.12707(12) 0.8277(2) 0.75804(15) 0.1010(8) Uani 1 1 d . . . . .
C12 C 0.57709(13) 0.2895(2) 0.62560(10) 0.0340(4) Uani 1 1 d . . . . .
C6 C 0.55435(13) 0.3405(2) 0.50001(10) 0.0369(5) Uani 1 1 d . . . . .
F52 F -0.05855(13) -0.3327(3) 0.44986(15) 0.1076(8) Uani 1 1 d . . . . .
C13 C 0.61490(13) 0.3059(2) 0.69659(10) 0.0349(4) Uani 1 1 d . . . . .
C3 C 0.51472(13) 0.1895(2) 0.60754(10) 0.0336(4) Uani 1 1 d . . . . .
C39 C 0.36442(13) 0.0442(2) 0.45444(10) 0.0383(5) Uani 1 1 d . . . . .
C11 C 0.59570(13) 0.3644(2) 0.57247(10) 0.0355(5) Uani 1 1 d . . . . .
C2 C 0.50095(12) 0.1210(2) 0.66319(10) 0.0339(4) Uani 1 1 d . . . . .
C38 C 0.40862(13) 0.0720(2) 0.52443(10) 0.0357(5) Uani 1 1 d . . . . .
C14 C 0.64420(13) 0.0535(2) 0.77759(10) 0.0347(4) Uani 1 1 d . . . . .
C4 C 0.47072(12) 0.1677(2) 0.53712(10) 0.0340(4) Uani 1 1 d . . . . .
C10 C 0.65585(13) 0.4624(2) 0.59392(11) 0.0361(5) Uani 1 1 d . . . . .
C21 C 0.69395(13) 0.4819(2) 0.66663(11) 0.0372(5) Uani 1 1 d . . . . .
C44 C 0.39164(13) 0.0063(2) 0.58169(10) 0.0359(5) Uani 1 1 d . . . . .
C45 C 0.32475(13) -0.0903(2) 0.56827(11) 0.0383(5) Uani 1 1 d . . . . .
C43 C 0.43750(13) 0.0297(2) 0.65047(10) 0.0359(5) Uani 1 1 d . . . . .
H43 H 0.426003 -0.014893 0.687411 0.043 Uiso 1 1 calc R U . . .
C19 C 0.61855(14) -0.0803(2) 0.77769(11) 0.0400(5) Uani 1 1 d . . . . .
H19 H 0.564813 -0.101465 0.757825 0.048 Uiso 1 1 calc R U . . .
C24 C 0.67464(13) 0.4049(2) 0.71740(10) 0.0366(5) Uani 1 1 d . . . . .
H24 H 0.700915 0.418602 0.764615 0.044 Uiso 1 1 calc R U . . .
F30 F 1.09202(14) 0.7216(3) 0.66200(13) 0.1165(9) Uani 1 1 d . . . . .
C9 C 0.67691(14) 0.5398(2) 0.54226(11) 0.0394(5) Uani 1 1 d . . . . .
C42 C 0.30101(14) -0.0587(3) 0.43929(11) 0.0425(5) Uani 1 1 d . . . . .
C5 C 0.48966(13) 0.2392(2) 0.48174(10) 0.0367(5) Uani 1 1 d . . . . .
C40 C 0.38330(14) 0.1120(3) 0.40076(11) 0.0423(5) Uani 1 1 d . . . . .
H40 H 0.354600 0.092779 0.354661 0.051 Uiso 1 1 calc R U . . .
C41 C 0.44422(14) 0.2085(3) 0.41372(11) 0.0412(5) Uani 1 1 d . . . . .
H41 H 0.454576 0.253012 0.376250 0.049 Uiso 1 1 calc R U . . .
C7 C 0.57825(15) 0.4169(3) 0.45099(11) 0.0425(5) Uani 1 1 d . . . . .
H7 H 0.553958 0.402502 0.403470 0.051 Uiso 1 1 calc R U . . .
C22 C 0.75594(14) 0.5879(2) 0.68880(12) 0.0406(5) Uani 1 1 d . . . . .
C18 C 0.67203(15) -0.1804(2) 0.80682(13) 0.0448(5) Uani 1 1 d . . . . .
H18 H 0.654702 -0.269353 0.805623 0.054 Uiso 1 1 calc R U . . .
C20 C 0.73851(15) 0.6458(3) 0.56290(12) 0.0442(5) Uani 1 1 d . . . . .
C8 C 0.63810(15) 0.5147(3) 0.47201(12) 0.0434(5) Uani 1 1 d . . . . .
H8 H 0.652395 0.564532 0.438004 0.052 Uiso 1 1 calc R U . . .
C17 C 0.75176(15) -0.1495(3) 0.83802(13) 0.0472(6) Uani 1 1 d . . . . .
H17 H 0.787892 -0.217331 0.858285 0.057 Uiso 1 1 calc R U . . .
C25 C 0.83948(15) 0.7605(2) 0.65808(14) 0.0470(6) Uani 1 1 d . . . . .
H25A H 0.836684 0.800923 0.701579 0.056 Uiso 1 1 calc R U . . .
H25B H 0.831033 0.831219 0.623055 0.056 Uiso 1 1 calc R U . . .
C26 C 0.92155(16) 0.6985(2) 0.66878(13) 0.0466(6) Uani 1 1 d . . . . .
C48 C 0.14004(15) -0.1631(3) 0.47848(12) 0.0455(5) Uani 1 1 d . . . . .
C15 C 0.72462(15) 0.0831(3) 0.80838(14) 0.0500(6) Uani 1 1 d . . . . .
H15 H 0.742793 0.171339 0.808328 0.060 Uiso 1 1 calc R U . . .
C47 C 0.22166(14) -0.2208(3) 0.48398(13) 0.0457(5) Uani 1 1 d . . . . .
H47A H 0.235451 -0.286833 0.521498 0.055 Uiso 1 1 calc R U . . .
H47B H 0.219831 -0.266924 0.440649 0.055 Uiso 1 1 calc R U . . .
C16 C 0.77739(16) -0.0180(3) 0.83896(16) 0.0567(7) Uani 1 1 d . . . . .
H16 H 0.830860 0.002869 0.860453 0.068 Uiso 1 1 calc R U . . .
C50 C -0.01174(18) -0.2264(4) 0.45542(19) 0.0696(9) Uani 1 1 d . . . . .
C27 C 0.98984(17) 0.7928(3) 0.70734(14) 0.0507(6) Uani 1 1 d . . . . .
C28 C 1.07495(19) 0.7411(3) 0.72118(18) 0.0625(7) Uani 1 1 d . . . . .
C49 C 0.07502(17) -0.2719(3) 0.46618(14) 0.0560(7) 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 0.0181 0.0091 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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
O60 P1 C14 113.86(9) . . ?
O60 P1 C2 113.44(9) . . ?
C14 P1 C2 108.22(10) . . ?
O60 P1 C13 118.51(10) . . ?
C14 P1 C13 108.22(10) . . ?
C2 P1 C13 92.34(9) . . ?
C45 N46 C42 125.6(2) . . ?
C45 N46 C47 116.84(19) . . ?
C42 N46 C47 117.44(19) . . ?
C22 N23 C20 125.8(2) . . ?
C22 N23 C25 116.3(2) . . ?
C20 N23 C25 117.7(2) . . ?
C13 C12 C11 124.1(2) . . ?
C13 C12 C3 115.92(19) . . ?
C11 C12 C3 119.93(19) . . ?
C7 C6 C11 116.9(2) . . ?
C7 C6 C5 124.08(19) . . ?
C11 C6 C5 119.06(19) . . ?
C12 C13 C24 118.4(2) . . ?
C12 C13 P1 107.61(16) . . ?
C24 C13 P1 133.97(15) . . ?
C2 C3 C4 123.7(2) . . ?
C2 C3 C12 115.69(18) . . ?
C4 C3 C12 120.58(19) . . ?
C40 C39 C38 119.1(2) . . ?
C40 C39 C42 120.84(19) . . ?
C38 C39 C42 120.1(2) . . ?
C10 C11 C12 116.87(19) . . ?
C10 C11 C6 122.29(19) . . ?
C12 C11 C6 120.8(2) . . ?
C3 C2 C43 119.17(19) . . ?
C3 C2 P1 108.38(16) . . ?
C43 C2 P1 132.30(16) . . ?
C4 C38 C39 118.7(2) . . ?
C4 C38 C44 119.68(18) . . ?
C39 C38 C44 121.6(2) . . ?
C15 C14 C19 118.8(2) . . ?
C15 C14 P1 121.95(18) . . ?
C19 C14 P1 119.04(16) . . ?
C38 C4 C3 116.80(19) . . ?
C38 C4 C5 122.31(18) . . ?
C3 C4 C5 120.9(2) . . ?
C11 C10 C9 118.87(19) . . ?
C11 C10 C21 119.46(19) . . ?
C9 C10 C21 121.7(2) . . ?
C24 C21 C10 122.0(2) . . ?
C24 C21 C22 118.98(19) . . ?
C10 C21 C22 119.1(2) . . ?
C43 C44 C38 121.5(2) . . ?
C43 C44 C45 119.03(19) . . ?
C38 C44 C45 119.50(19) . . ?
O58 C45 N46 120.0(2) . . ?
O58 C45 C44 123.31(19) . . ?
N46 C45 C44 116.69(19) . . ?
C44 C43 C2 119.0(2) . . ?
C18 C19 C14 120.5(2) . . ?
C21 C24 C13 119.12(19) . . ?
C8 C9 C10 118.9(2) . . ?
C8 C9 C20 120.7(2) . . ?
C10 C9 C20 120.4(2) . . ?
O59 C42 N46 120.5(2) . . ?
O59 C42 C39 123.1(2) . . ?
N46 C42 C39 116.37(18) . . ?
C41 C5 C4 116.8(2) . . ?
C41 C5 C6 124.6(2) . . ?
C4 C5 C6 118.62(18) . . ?
C39 C40 C41 122.0(2) . . ?
C5 C41 C40 121.1(2) . . ?
C6 C7 C8 121.1(2) . . ?
O36 C22 N23 120.6(2) . . ?
O36 C22 C21 122.4(2) . . ?
N23 C22 C21 116.9(2) . . ?
C19 C18 C17 120.2(2) . . ?
O37 C20 N23 120.9(2) . . ?
O37 C20 C9 123.2(2) . . ?
N23 C20 C9 115.9(2) . . ?
C9 C8 C7 121.9(2) . . ?
C16 C17 C18 119.8(2) . . ?
N23 C25 C26 110.9(2) . . ?
F35 C26 F34 105.8(2) . . ?
F35 C26 C25 110.6(2) . . ?
F34 C26 C25 110.9(2) . . ?
F35 C26 C27 108.8(2) . . ?
F34 C26 C27 107.5(2) . . ?
C25 C26 C27 112.9(2) . . ?
F57 C48 F56 106.3(2) . . ?
F57 C48 C47 111.1(2) . . ?
F56 C48 C47 110.93(19) . . ?
F57 C48 C49 108.41(19) . . ?
F56 C48 C49 107.2(2) . . ?
C47 C48 C49 112.6(2) . . ?
C16 C15 C14 120.1(2) . . ?
N46 C47 C48 112.2(2) . . ?
C17 C16 C15 120.6(2) . . ?
F52 C50 F53 108.2(3) . . ?
F52 C50 F51 108.2(3) . . ?
F53 C50 F51 108.9(3) . . ?
F52 C50 C49 109.9(3) . . ?
F53 C50 C49 111.4(2) . . ?
F51 C50 C49 110.2(3) . . ?
F33 C27 F32 107.9(2) . . ?
F33 C27 C28 107.6(2) . . ?
F32 C27 C28 107.6(2) . . ?
F33 C27 C26 108.1(2) . . ?
F32 C27 C26 107.8(2) . . ?
C28 C27 C26 117.5(2) . . ?
F31 C28 F29 106.7(3) . . ?
F31 C28 F30 107.9(3) . . ?
F29 C28 F30 107.4(3) . . ?
F31 C28 C27 112.6(3) . . ?
F29 C28 C27 111.4(3) . . ?
F30 C28 C27 110.6(3) . . ?
F54 C49 F55 107.6(2) . . ?
F54 C49 C48 107.6(2) . . ?
F55 C49 C48 108.1(2) . . ?
F54 C49 C50 108.2(2) . . ?
F55 C49 C50 106.8(3) . . ?
C48 C49 C50 118.1(2) . . ?
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
P1 O60 1.4797(15) . ?
P1 C14 1.792(2) . ?
P1 C2 1.826(2) . ?
P1 C13 1.839(2) . ?
F34 C26 1.350(3) . ?
F56 C48 1.355(3) . ?
F57 C48 1.345(3) . ?
F35 C26 1.349(3) . ?
F33 C27 1.336(3) . ?
O58 C45 1.213(3) . ?
O36 C22 1.208(3) . ?
O59 C42 1.214(3) . ?
F32 C27 1.341(3) . ?
F55 C49 1.346(3) . ?
O37 C20 1.212(3) . ?
N46 C45 1.408(3) . ?
N46 C42 1.408(3) . ?
N46 C47 1.462(3) . ?
F54 C49 1.342(3) . ?
F53 C50 1.318(4) . ?
F51 C50 1.327(4) . ?
N23 C22 1.407(3) . ?
N23 C20 1.410(3) . ?
N23 C25 1.464(3) . ?
F31 C28 1.297(4) . ?
F29 C28 1.310(4) . ?
C12 C13 1.387(3) . ?
C12 C11 1.408(3) . ?
C12 C3 1.439(3) . ?
C6 C7 1.393(3) . ?
C6 C11 1.435(3) . ?
C6 C5 1.475(3) . ?
F52 C50 1.318(4) . ?
C13 C24 1.403(3) . ?
C3 C2 1.381(3) . ?
C3 C4 1.408(3) . ?
C39 C40 1.383(3) . ?
C39 C38 1.412(3) . ?
C39 C42 1.470(4) . ?
C11 C10 1.402(3) . ?
C2 C43 1.395(3) . ?
C38 C4 1.406(3) . ?
C38 C44 1.420(3) . ?
C14 C15 1.390(3) . ?
C14 C19 1.399(3) . ?
C4 C5 1.430(3) . ?
C10 C9 1.417(3) . ?
C10 C21 1.422(3) . ?
C21 C24 1.386(3) . ?
C21 C22 1.480(3) . ?
C44 C43 1.392(3) . ?
C44 C45 1.473(3) . ?
C19 C18 1.370(3) . ?
F30 C28 1.314(4) . ?
C9 C8 1.390(3) . ?
C9 C20 1.474(4) . ?
C5 C41 1.392(3) . ?
C40 C41 1.397(4) . ?
C7 C8 1.397(4) . ?
C18 C17 1.384(4) . ?
C17 C16 1.376(4) . ?
C25 C26 1.516(4) . ?
C26 C27 1.534(4) . ?
C48 C47 1.510(4) . ?
C48 C49 1.532(4) . ?
C15 C16 1.377(4) . ?
C50 C49 1.535(5) . ?
C27 C28 1.519(4) . ?
