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#$Date: 2025-08-23 00:12:46 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301866 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/44/7234419.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_7234419
loop_
_publ_author_name
'Guo-Ping Yong'
'Chen Shen'
'Cong Zhang'
'Yu-Mei Zhao'
_publ_section_title
;
 Morphology-controllable fabrication of organic microcrystals by
 solid-phase reactions: revealing morphology-sensitive highly efficient
 phosphorescence and enhanced near-infrared absorption
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              9048
_journal_page_last               9052
_journal_paper_doi               10.1039/C5TC01770J
_journal_volume                  3
_journal_year                    2015
_chemical_formula_sum            'C14 H10 B Cl F2 N4 O5'
_chemical_formula_weight         398.52
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 97.992(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.522(4)
_cell_length_b                   5.1557(9)
_cell_length_c                   15.049(3)
_cell_measurement_temperature    296(2)
_cell_volume                     1576.8(5)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-2014
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11547
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.275
_diffrn_reflns_theta_min         1.002
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.303
_exptl_absorpt_correction_T_max  0.916
_exptl_absorpt_correction_T_min  0.893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.679
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       columnar
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.716
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       0.0116(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3270
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0409
_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)+(0.0686P)²+0.7448P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1281
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2774
_reflns_number_total             3270
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            J-Mater-Chem-C-2015-3-9048.cif
_cod_data_source_block           2
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7234419
_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
C1 C 0.12987(10) 0.0198(5) 0.69699(15) 0.0397(5) Uani 1 1 d . . . . .
C2 C 0.06154(11) 0.0031(5) 0.67331(18) 0.0507(6) Uani 1 1 d . . . . .
H2A H 0.0333 0.0991 0.7038 0.061 Uiso 1 1 calc R U . . .
C3 C 0.03744(12) -0.1564(7) 0.6049(2) 0.0623(8) Uani 1 1 d . . . . .
H3A H -0.0078 -0.1707 0.5886 0.075 Uiso 1 1 calc R U . . .
C4 C 0.08026(13) -0.3010(7) 0.5581(2) 0.0670(8) Uani 1 1 d . . . . .
H4A H 0.0629 -0.4068 0.5105 0.080 Uiso 1 1 calc R U . . .
C5 C 0.14594(12) -0.2869(6) 0.58166(18) 0.0572(7) Uani 1 1 d . . . . .
H5A H 0.1742 -0.3839 0.5515 0.069 Uiso 1 1 calc R U . . .
C6 C 0.23528(10) -0.0763(4) 0.68670(15) 0.0391(5) Uani 1 1 d . . . . .
H6A H 0.2727 -0.1500 0.6687 0.047 Uiso 1 1 calc R U . . .
C7 C 0.23315(9) 0.1006(4) 0.75242(14) 0.0329(4) Uani 1 1 d . . . . .
C8 C 0.27976(9) 0.2511(4) 0.81059(13) 0.0324(4) Uani 1 1 d . . . . .
C9 C 0.39318(10) 0.0905(4) 0.79434(13) 0.0311(4) Uani 1 1 d . . . . .
H9A H 0.3791 -0.0494 0.7576 0.037 Uiso 1 1 calc R U . . .
C10 C 0.45824(10) 0.1369(4) 0.81859(13) 0.0346(4) Uani 1 1 d . . . . .
H10A H 0.4890 0.0249 0.7995 0.042 Uiso 1 1 calc R U . . .
C11 C 0.47997(10) 0.3517(4) 0.87221(13) 0.0356(5) Uani 1 1 d . . . . .
H11A H 0.5248 0.3837 0.8867 0.043 Uiso 1 1 calc R U . . .
C12 C 0.43521(10) 0.5145(4) 0.90332(13) 0.0340(4) Uani 1 1 d . . . . .
H12A H 0.4489 0.6565 0.9393 0.041 Uiso 1 1 calc R U . . .
C13 C 0.36884(10) 0.4601(4) 0.87930(13) 0.0306(4) Uani 1 1 d . . . . .
C14 C 0.25992(10) 0.4544(4) 0.85894(14) 0.0350(5) Uani 1 1 d . . . . .
B1 B 0.14474(12) 0.3466(6) 0.83277(18) 0.0414(6) Uani 1 1 d . . . . .
Cl1 Cl 0.35636(2) 0.42537(10) 0.57796(3) 0.03577(19) Uani 1 1 d . . . . .
F1 F 0.09198(7) 0.4889(3) 0.79557(11) 0.0599(4) Uani 1 1 d . . . . .
F2 F 0.12988(8) 0.2007(3) 0.90326(10) 0.0628(4) Uani 1 1 d . . . . .
N1 N 0.17036(9) -0.1259(4) 0.65138(13) 0.0417(4) Uani 1 1 d . . . . .
N2 N 0.16787(8) 0.1617(4) 0.75945(12) 0.0370(4) Uani 1 1 d . . . . .
N3 N 0.34849(8) 0.2536(3) 0.82496(10) 0.0282(4) Uani 1 1 d . . . . .
N4 N 0.31406(9) 0.5827(4) 0.89931(13) 0.0364(4) Uani 1 1 d . . . . .
H4 H 0.3119(12) 0.682(5) 0.9341(18) 0.040(7) Uiso 1 1 d . . . . .
O1 O 0.19974(7) 0.5290(3) 0.86483(11) 0.0453(4) Uani 1 1 d . . . . .
O2 O 0.29494(10) 0.5126(5) 0.53075(15) 0.0776(7) Uani 1 1 d . . . . .
O3 O 0.36976(10) 0.5585(3) 0.66185(11) 0.0516(4) Uani 1 1 d . . . . .
O4 O 0.40584(11) 0.4923(4) 0.52367(13) 0.0720(6) Uani 1 1 d . . . . .
O5 O 0.35674(10) 0.1518(3) 0.59107(12) 0.0559(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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
N2 C1 N1 108.25(18) . .
N2 C1 C2 132.2(2) . .
N1 C1 C2 119.6(2) . .
C3 C2 C1 118.5(2) . .
C2 C3 C4 120.8(2) . .
C5 C4 C3 120.6(3) . .
C4 C5 N1 118.6(2) . .
C7 C6 N1 106.13(18) . .
C6 C7 N2 109.71(18) . .
C6 C7 C8 136.61(18) . .
N2 C7 C8 113.49(18) . .
C14 C8 N3 106.20(17) . .
C14 C8 C7 121.11(18) . .
N3 C8 C7 132.37(18) . .
C10 C9 N3 118.77(18) . .
C9 C10 C11 121.03(19) . .
C12 C11 C10 120.21(19) . .
C11 C12 C13 117.78(19) . .
N4 C13 N3 107.47(17) . .
N4 C13 C12 131.30(19) . .
N3 C13 C12 121.23(18) . .
O1 C14 N4 123.12(19) . .
O1 C14 C8 127.9(2) . .
N4 C14 C8 108.93(18) . .
F1 B1 F2 111.37(19) . .
F1 B1 O1 108.3(2) . .
F2 B1 O1 109.6(2) . .
F1 B1 N2 109.7(2) . .
F2 B1 N2 109.3(2) . .
O1 B1 N2 108.54(16) . .
O5 Cl1 O3 110.88(11) . .
O5 Cl1 O2 111.58(13) . .
O3 Cl1 O2 109.61(13) . .
O5 Cl1 O4 109.10(12) . .
O3 Cl1 O4 108.88(12) . .
O2 Cl1 O4 106.66(15) . .
C1 N1 C5 121.97(19) . .
C1 N1 C6 108.87(18) . .
C5 N1 C6 129.2(2) . .
C1 N2 C7 107.04(17) . .
C1 N2 B1 127.76(17) . .
C7 N2 B1 125.04(18) . .
C9 N3 C13 120.95(17) . .
C9 N3 C8 130.60(17) . .
C13 N3 C8 108.45(16) . .
C13 N4 C14 108.91(18) . .
C14 O1 B1 118.04(18) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N2 1.350(3) .
C1 N1 1.373(3) .
C1 C2 1.401(3) .
C2 C3 1.356(4) .
C3 C4 1.413(4) .
C4 C5 1.347(4) .
C5 N1 1.377(3) .
C6 C7 1.351(3) .
C6 N1 1.388(3) .
C7 N2 1.394(2) .
C7 C8 1.432(3) .
C8 C14 1.370(3) .
C8 N3 1.397(2) .
C9 C10 1.356(3) .
C9 N3 1.370(2) .
C10 C11 1.406(3) .
C11 C12 1.374(3) .
C12 C13 1.388(3) .
C13 N4 1.359(3) .
C13 N3 1.372(3) .
C14 O1 1.308(2) .
C14 N4 1.361(3) .
B1 F1 1.362(3) .
B1 F2 1.369(3) .
B1 O1 1.497(3) .
B1 N2 1.580(3) .
Cl1 O5 1.4238(18) .
Cl1 O3 1.4296(17) .
Cl1 O2 1.431(2) .
Cl1 O4 1.4313(18) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168338977
