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#$Date: 2025-08-23 02:36:08 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301880 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/00/04/8000495.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_8000495
loop_
_publ_author_name
'Ding, Zeyang'
'Shang, Hongxing'
'Geng, Yijia'
'Zhang, Shi-Tong'
'Huo, Zepeng'
'Yang, Zairan'
'Li, Bao'
'Xu, Weiqing'
'Jiang, Shimei'
_publ_section_title
;
 Tuning Organic Microcrystal Morphologies through Crystal Engineering
 Strategies toward Anisotropic Optical Waveguide.
;
_journal_issue                   19
_journal_name_full               'The journal of physical chemistry letters'
_journal_page_first              4585
_journal_page_last               4592
_journal_paper_doi               10.1021/acs.jpclett.1c00769
_journal_volume                  12
_journal_year                    2021
_chemical_formula_moiety         'C28 H16 F6 N2'
_chemical_formula_sum            'C28 H16 F6 N2'
_chemical_formula_weight         494.43
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.54(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.799(3)
_cell_length_b                   9.962(2)
_cell_length_c                   15.092(3)
_cell_measurement_reflns_used    16166
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      3.02
_cell_volume                     2224.9(8)
_computing_cell_refinement       RAPID-AUTO
_computing_data_collection       'RAPID-AUTO (Rigaku Corporation, 1998)'
_computing_data_reduction
'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0185
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20700
_diffrn_reflns_theta_full        27.43
_diffrn_reflns_theta_max         27.43
_diffrn_reflns_theta_min         3.02
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  0.9879
_exptl_absorpt_correction_T_min  0.9843
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.753
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         5059
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0553
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0907P)²+0.8709P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1638
_refine_ls_wR_factor_ref         0.1737
_reflns_number_gt                3990
_reflns_number_total             5059
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1.CIF
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 8000494--8000495.cif.'
_cod_original_cell_volume        2224.8(8)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8000495
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.17963(16) 0.5299(3) 0.68159(16) 0.0553(6) Uani 1 1 d . . .
H1 H 0.1397 0.6020 0.6811 0.066 Uiso 1 1 calc R . .
C2 C 0.23710(14) 0.5159(2) 0.61041(14) 0.0466(5) Uani 1 1 d . . .
H2 H 0.2357 0.5780 0.5644 0.056 Uiso 1 1 calc R . .
C3 C 0.29673(12) 0.40883(19) 0.60796(12) 0.0370(4) Uani 1 1 d . . .
C4 C 0.29655(15) 0.3234(2) 0.68024(14) 0.0489(5) Uani 1 1 d . . .
H4 H 0.3362 0.2510 0.6828 0.059 Uiso 1 1 calc R . .
C5 C 0.23692(16) 0.3464(3) 0.74887(15) 0.0545(5) Uani 1 1 d . . .
H5 H 0.2383 0.2877 0.7968 0.065 Uiso 1 1 calc R . .
C6 C 0.35687(12) 0.38731(18) 0.53093(12) 0.0360(4) Uani 1 1 d . . .
C7 C 0.32724(12) 0.4217(2) 0.44593(13) 0.0423(4) Uani 1 1 d . . .
H7 H 0.2687 0.4537 0.4378 0.051 Uiso 1 1 calc R . .
C8 C 0.38310(13) 0.4093(2) 0.37337(13) 0.0431(4) Uani 1 1 d . . .
H8 H 0.3614 0.4326 0.3174 0.052 Uiso 1 1 calc R . .
C9 C 0.47195(12) 0.36208(18) 0.38309(12) 0.0366(4) Uani 1 1 d . . .
C10 C 0.50022(12) 0.3224(2) 0.46790(13) 0.0400(4) Uani 1 1 d . . .
H10 H 0.5579 0.2871 0.4758 0.048 Uiso 1 1 calc R . .
C11 C 0.44390(13) 0.3347(2) 0.54033(13) 0.0404(4) Uani 1 1 d . . .
H11 H 0.4644 0.3076 0.5960 0.048 Uiso 1 1 calc R . .
C12 C 0.53795(12) 0.3551(2) 0.31152(13) 0.0390(4) Uani 1 1 d . . .
H12 H 0.5906 0.3085 0.3257 0.047 Uiso 1 1 calc R . .
C13 C 0.53493(11) 0.40515(18) 0.22828(12) 0.0358(4) Uani 1 1 d . . .
C14 C 0.45878(12) 0.4807(2) 0.19544(12) 0.0393(4) Uani 1 1 d . . .
C15 C 0.61041(11) 0.39201(18) 0.16417(12) 0.0357(4) Uani 1 1 d . . .
C16 C 0.62103(13) 0.4864(2) 0.09670(13) 0.0411(4) Uani 1 1 d . . .
H16 H 0.5789 0.5551 0.0902 0.049 Uiso 1 1 calc R . .
C17 C 0.69325(13) 0.4793(2) 0.03940(13) 0.0411(4) Uani 1 1 d . . .
H17 H 0.6997 0.5443 -0.0043 0.049 Uiso 1 1 calc R . .
C18 C 0.75642(12) 0.37622(19) 0.04624(12) 0.0365(4) Uani 1 1 d . . .
C19 C 0.74361(13) 0.2794(2) 0.11139(14) 0.0439(5) Uani 1 1 d . . .
H19 H 0.7840 0.2081 0.1158 0.053 Uiso 1 1 calc R . .
C20 C 0.67200(13) 0.2866(2) 0.16985(14) 0.0434(4) Uani 1 1 d . . .
H20 H 0.6651 0.2208 0.2130 0.052 Uiso 1 1 calc R . .
C21 C 0.83599(12) 0.37046(19) -0.01337(12) 0.0365(4) Uani 1 1 d . . .
C22 C 0.83244(12) 0.4257(2) -0.09820(12) 0.0387(4) Uani 1 1 d . . .
H22 H 0.7790 0.4637 -0.1192 0.046 Uiso 1 1 calc R . .
C23 C 0.90855(12) 0.42436(19) -0.15169(12) 0.0379(4) Uani 1 1 d . . .
C24 C 0.98870(12) 0.3661(2) -0.12314(12) 0.0390(4) Uani 1 1 d . . .
H24 H 1.0394 0.3660 -0.1591 0.047 Uiso 1 1 calc R . .
C25 C 0.99146(12) 0.30818(19) -0.03994(13) 0.0386(4) Uani 1 1 d . . .
C26 C 0.91654(12) 0.3115(2) 0.01513(12) 0.0395(4) Uani 1 1 d . . .
H26 H 0.9203 0.2739 0.0715 0.047 Uiso 1 1 calc R . .
C27 C 0.90528(15) 0.4873(2) -0.24178(13) 0.0476(5) Uani 1 1 d . . .
C28 C 1.07557(13) 0.2373(2) -0.00904(14) 0.0466(5) Uani 1 1 d . . .
F1 F 0.82132(10) 0.5115(2) -0.27032(10) 0.0813(5) Uani 1 1 d . . .
F2 F 0.95006(14) 0.60189(17) -0.24480(11) 0.0842(5) Uani 1 1 d . . .
F3 F 0.94203(12) 0.40956(18) -0.30322(9) 0.0781(5) Uani 1 1 d . . .
F4 F 1.08710(12) 0.2411(2) 0.07687(11) 0.0994(7) Uani 1 1 d . . .
F5 F 1.14988(10) 0.2889(2) -0.04211(15) 0.1059(8) Uani 1 1 d . . .
F6 F 1.07564(14) 0.11154(19) -0.03162(18) 0.1154(9) Uani 1 1 d . . .
N1 N 0.17789(13) 0.4469(2) 0.75065(12) 0.0544(5) Uani 1 1 d . . .
N2 N 0.39924(12) 0.5399(2) 0.16655(13) 0.0540(5) 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'
F F 0.0171 0.0103 '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
N1 C1 C2 124.2(2) . . ?
N1 C1 H1 117.9 . . ?
C2 C1 H1 117.9 . . ?
C1 C2 C3 119.7(2) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 116.53(17) . . ?
C4 C3 C6 122.25(17) . . ?
C2 C3 C6 121.22(17) . . ?
C3 C4 C5 119.6(2) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
N1 C5 C4 124.3(2) . . ?
N1 C5 H5 117.9 . . ?
C4 C5 H5 117.9 . . ?
C7 C6 C11 117.87(16) . . ?
C7 C6 C3 119.91(16) . . ?
C11 C6 C3 122.22(17) . . ?
C8 C7 C6 121.40(17) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C7 C8 C9 120.89(18) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C10 C9 C8 117.52(16) . . ?
C10 C9 C12 117.73(17) . . ?
C8 C9 C12 124.72(17) . . ?
C11 C10 C9 121.29(17) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C6 120.92(17) . . ?
C10 C11 H11 119.5 . . ?
C6 C11 H11 119.5 . . ?
C13 C12 C9 130.63(18) . . ?
C13 C12 H12 114.7 . . ?
C9 C12 H12 114.7 . . ?
C12 C13 C14 122.13(16) . . ?
C12 C13 C15 123.53(17) . . ?
C14 C13 C15 114.30(16) . . ?
N2 C14 C13 177.7(2) . . ?
C20 C15 C16 118.34(16) . . ?
C20 C15 C13 121.36(16) . . ?
C16 C15 C13 120.31(16) . . ?
C17 C16 C15 120.98(17) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C18 120.91(17) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C19 C18 C17 117.91(16) . . ?
C19 C18 C21 120.90(16) . . ?
C17 C18 C21 121.18(16) . . ?
C20 C19 C18 121.55(18) . . ?
C20 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C19 C20 C15 120.24(18) . . ?
C19 C20 H20 119.9 . . ?
C15 C20 H20 119.9 . . ?
C26 C21 C22 118.34(16) . . ?
C26 C21 C18 120.57(16) . . ?
C22 C21 C18 121.08(16) . . ?
C23 C22 C21 120.34(17) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C24 C23 C22 121.24(17) . . ?
C24 C23 C27 118.56(16) . . ?
C22 C23 C27 120.20(17) . . ?
C25 C24 C23 118.38(16) . . ?
C25 C24 H24 120.8 . . ?
C23 C24 H24 120.8 . . ?
C24 C25 C26 121.04(17) . . ?
C24 C25 C28 119.73(16) . . ?
C26 C25 C28 119.21(17) . . ?
C25 C26 C21 120.62(17) . . ?
C25 C26 H26 119.7 . . ?
C21 C26 H26 119.7 . . ?
F2 C27 F3 105.73(18) . . ?
F2 C27 F1 107.4(2) . . ?
F3 C27 F1 105.43(19) . . ?
F2 C27 C23 112.41(18) . . ?
F3 C27 C23 112.29(18) . . ?
F1 C27 C23 113.01(17) . . ?
F6 C28 F4 106.8(2) . . ?
F6 C28 F5 106.0(2) . . ?
F4 C28 F5 105.2(2) . . ?
F6 C28 C25 112.04(19) . . ?
F4 C28 C25 113.23(17) . . ?
F5 C28 C25 113.03(18) . . ?
C5 N1 C1 115.76(18) . . ?
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
C1 N1 1.331(3) . ?
C1 C2 1.383(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.385(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.384(3) . ?
C3 C6 1.486(2) . ?
C4 C5 1.386(3) . ?
C4 H4 0.9300 . ?
C5 N1 1.329(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.395(3) . ?
C6 C11 1.396(3) . ?
C7 C8 1.384(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.403(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.400(3) . ?
C9 C12 1.465(2) . ?
C10 C11 1.386(2) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.352(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.439(3) . ?
C13 C15 1.490(2) . ?
C14 N2 1.143(3) . ?
C15 C20 1.392(3) . ?
C15 C16 1.396(3) . ?
C16 C17 1.383(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.392(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.392(3) . ?
C18 C21 1.490(2) . ?
C19 C20 1.387(2) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C26 1.394(3) . ?
C21 C22 1.394(3) . ?
C22 C23 1.392(2) . ?
C22 H22 0.9300 . ?
C23 C24 1.386(3) . ?
C23 C27 1.498(3) . ?
C24 C25 1.382(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.392(2) . ?
C25 C28 1.502(3) . ?
C26 H26 0.9300 . ?
C27 F2 1.321(3) . ?
C27 F3 1.329(2) . ?
C27 F1 1.333(3) . ?
C28 F6 1.298(3) . ?
C28 F4 1.307(3) . ?
C28 F5 1.317(3) . ?
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
_geom_torsion_publ_flag
N1 C1 C2 C3 0.9(4) . . . . ?
C1 C2 C3 C4 -2.0(3) . . . . ?
C1 C2 C3 C6 177.5(2) . . . . ?
C2 C3 C4 C5 1.4(3) . . . . ?
C6 C3 C4 C5 -178.0(2) . . . . ?
C3 C4 C5 N1 0.2(4) . . . . ?
C4 C3 C6 C7 146.0(2) . . . . ?
C2 C3 C6 C7 -33.5(3) . . . . ?
C4 C3 C6 C11 -34.9(3) . . . . ?
C2 C3 C6 C11 145.6(2) . . . . ?
C11 C6 C7 C8 -2.4(3) . . . . ?
C3 C6 C7 C8 176.73(18) . . . . ?
C6 C7 C8 C9 -0.3(3) . . . . ?
C7 C8 C9 C10 2.9(3) . . . . ?
C7 C8 C9 C12 -175.21(19) . . . . ?
C8 C9 C10 C11 -2.7(3) . . . . ?
C12 C9 C10 C11 175.50(18) . . . . ?
C9 C10 C11 C6 0.0(3) . . . . ?
C7 C6 C11 C10 2.6(3) . . . . ?
C3 C6 C11 C10 -176.55(18) . . . . ?
C10 C9 C12 C13 -168.3(2) . . . . ?
C8 C9 C12 C13 9.8(3) . . . . ?
C9 C12 C13 C14 0.4(3) . . . . ?
C9 C12 C13 C15 178.02(18) . . . . ?
C12 C13 C14 N2 -161(5) . . . . ?
C15 C13 C14 N2 21(6) . . . . ?
C12 C13 C15 C20 26.2(3) . . . . ?
C14 C13 C15 C20 -156.06(18) . . . . ?
C12 C13 C15 C16 -153.6(2) . . . . ?
C14 C13 C15 C16 24.2(2) . . . . ?
C20 C15 C16 C17 -3.0(3) . . . . ?
C13 C15 C16 C17 176.79(18) . . . . ?
C15 C16 C17 C18 1.3(3) . . . . ?
C16 C17 C18 C19 1.2(3) . . . . ?
C16 C17 C18 C21 -177.99(18) . . . . ?
C17 C18 C19 C20 -2.0(3) . . . . ?
C21 C18 C19 C20 177.18(19) . . . . ?
C18 C19 C20 C15 0.3(3) . . . . ?
C16 C15 C20 C19 2.2(3) . . . . ?
C13 C15 C20 C19 -177.61(18) . . . . ?
C19 C18 C21 C26 -28.4(3) . . . . ?
C17 C18 C21 C26 150.7(2) . . . . ?
C19 C18 C21 C22 152.7(2) . . . . ?
C17 C18 C21 C22 -28.1(3) . . . . ?
C26 C21 C22 C23 -1.5(3) . . . . ?
C18 C21 C22 C23 177.36(18) . . . . ?
C21 C22 C23 C24 1.3(3) . . . . ?
C21 C22 C23 C27 -178.23(19) . . . . ?
C22 C23 C24 C25 0.4(3) . . . . ?
C27 C23 C24 C25 179.95(18) . . . . ?
C23 C24 C25 C26 -1.9(3) . . . . ?
C23 C24 C25 C28 176.50(19) . . . . ?
C24 C25 C26 C21 1.7(3) . . . . ?
C28 C25 C26 C21 -176.70(19) . . . . ?
C22 C21 C26 C25 0.1(3) . . . . ?
C18 C21 C26 C25 -178.84(18) . . . . ?
C24 C23 C27 F2 -72.9(2) . . . . ?
C22 C23 C27 F2 106.6(2) . . . . ?
C24 C23 C27 F3 46.1(3) . . . . ?
C22 C23 C27 F3 -134.3(2) . . . . ?
C24 C23 C27 F1 165.24(19) . . . . ?
C22 C23 C27 F1 -15.2(3) . . . . ?
C24 C25 C28 F6 -88.5(3) . . . . ?
C26 C25 C28 F6 89.9(3) . . . . ?
C24 C25 C28 F4 150.7(2) . . . . ?
C26 C25 C28 F4 -30.9(3) . . . . ?
C24 C25 C28 F5 31.2(3) . . . . ?
C26 C25 C28 F5 -150.4(2) . . . . ?
C4 C5 N1 C1 -1.3(4) . . . . ?
C2 C1 N1 C5 0.8(4) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102595963
