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#$Date: 2021-03-05 03:44:01 +0200 (Fri, 05 Mar 2021) $
#$Revision: 262559 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/21/7242192.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_7242192
loop_
_publ_author_name
'Jamadar, Akshoy'
'Karan, Chandan Kumar'
'Biswas, Subhendu'
'Das, Anindita'
_publ_section_title
;
 Structural influence on stimuli-responsive halogen-bonded luminescent
 supramolecular polymers from heteroditopic isomers
;
_journal_issue                   8
_journal_name_full               CrystEngComm
_journal_page_first              1695
_journal_page_last               1699
_journal_paper_doi               10.1039/D1CE00101A
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C15 H6 F4 I N O'
_chemical_formula_sum            'C15 H6 F4 I N O'
_chemical_formula_weight         419.11
_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-2018/1
_audit_update_record
;
2020-08-21 deposited with the CCDC.	2021-01-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.908(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6686(18)
_cell_length_b                   4.5292(7)
_cell_length_c                   25.933(4)
_cell_measurement_reflns_used    12588
_cell_measurement_temperature    161(2)
_cell_measurement_theta_max      27.233
_cell_measurement_theta_min      2.663
_cell_volume                     1335.9(4)
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      161(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8VENTURE with PHOTON II Detector'
_diffrn_measurement_method       'phi, omega and kappa scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1004
_diffrn_reflns_av_unetI/netI     0.0784
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            12588
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.233
_diffrn_reflns_theta_min         2.663
_diffrn_source                   Micro-focus
_exptl_absorpt_coefficient_mu    2.445
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.084
_exptl_crystal_description       needle
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         2.333
_refine_diff_density_min         -2.214
_refine_diff_density_rms         0.290
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.249
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2953
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.249
_refine_ls_R_factor_all          0.1034
_refine_ls_R_factor_gt           0.0930
_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)+(0.0001P)²+58.3568P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2381
_refine_ls_wR_factor_ref         0.2430
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2529
_reflns_number_total             2953
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce00101a2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7242192--7242194.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7242192
_shelx_shelxl_version_number     2018/1
_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
I1 I 0.25414(8) 0.0421(2) 0.91450(3) 0.0294(3) Uani 1 1 d . . . . .
F1 F 0.0863(7) 0.780(2) 0.7508(3) 0.035(2) Uani 1 1 d . . . . .
F2 F 0.0788(8) 0.489(2) 0.8414(3) 0.041(2) Uani 1 1 d . . . . .
O1 O 0.2701(9) 0.679(2) 0.7020(3) 0.031(2) Uani 1 1 d . . . . .
F4 F 0.4271(7) 0.239(2) 0.7405(3) 0.035(2) Uani 1 1 d . . . . .
F3 F 0.4206(7) -0.042(2) 0.8315(3) 0.038(2) Uani 1 1 d . . . . .
N1 N 0.2795(11) 0.697(3) 0.5172(4) 0.033(3) Uani 1 1 d . . . . .
C1 C 0.2521(12) 0.227(3) 0.8399(5) 0.026(3) Uani 1 1 d . . . . .
C2 C 0.1668(11) 0.425(3) 0.8185(5) 0.024(3) Uani 1 1 d . . . . .
C3 C 0.1703(12) 0.573(3) 0.7708(5) 0.026(3) Uani 1 1 d . . . . .
C4 C 0.2603(14) 0.522(3) 0.7434(5) 0.032(3) Uani 1 1 d . . . . .
C5 C 0.2242(13) 0.565(3) 0.6507(5) 0.029(3) Uani 1 1 d . . . . .
C6 C 0.2784(12) 0.686(3) 0.6115(5) 0.026(3) Uani 1 1 d . . . . .
C7 C 0.3698(12) 0.886(3) 0.6215(5) 0.029(3) Uani 1 1 d . . . . .
H7 H 0.401066 0.952380 0.656586 0.035 Uiso 1 1 calc R U . . .
C8 C 0.4145(13) 0.987(4) 0.5811(6) 0.033(3) Uani 1 1 d . . . . .
H8 H 0.477031 1.125936 0.587149 0.040 Uiso 1 1 calc R U . . .
C9 C 0.3650(13) 0.878(4) 0.5285(6) 0.035(3) Uani 1 1 d . . . . .
H9 H 0.398353 0.945969 0.500448 0.042 Uiso 1 1 calc R U . . .
C11 C 0.2331(12) 0.587(3) 0.5592(5) 0.029(3) Uani 1 1 d . . . . .
C12 C 0.1380(13) 0.386(4) 0.5474(6) 0.036(3) Uani 1 1 d . . . . .
H12 H 0.107393 0.325029 0.511949 0.044 Uiso 1 1 calc R U . . .
C13 C 0.0909(13) 0.280(4) 0.5871(6) 0.036(3) Uani 1 1 d . . . . .
H13 H 0.027191 0.144112 0.579118 0.043 Uiso 1 1 calc R U . . .
C14 C 0.1351(13) 0.368(3) 0.6399(6) 0.034(3) Uani 1 1 d . . . . .
H14 H 0.102764 0.289490 0.667564 0.040 Uiso 1 1 calc R U . . .
C15 C 0.3410(11) 0.300(3) 0.7657(5) 0.025(3) Uani 1 1 d . . . . .
C16 C 0.3383(11) 0.162(3) 0.8128(5) 0.025(3) 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'
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'
I I -0.4742 1.8119 '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
C4 O1 C5 119.2(12) . . ?
C9 N1 C11 117.7(12) . . ?
C2 C1 C16 118.7(12) . . ?
C2 C1 I1 119.6(10) . . ?
C16 C1 I1 121.6(10) . . ?
F2 C2 C1 121.9(13) . . ?
F2 C2 C3 117.6(11) . . ?
C1 C2 C3 120.5(12) . . ?
F1 C3 C4 118.1(12) . . ?
F1 C3 C2 119.7(11) . . ?
C4 C3 C2 122.1(12) . . ?
O1 C4 C3 122.3(14) . . ?
O1 C4 C15 123.3(13) . . ?
C3 C4 C15 114.4(11) . . ?
C14 C5 O1 123.2(13) . . ?
C14 C5 C6 123.3(13) . . ?
O1 C5 C6 113.4(12) . . ?
C7 C6 C11 119.8(13) . . ?
C7 C6 C5 124.4(12) . . ?
C11 C6 C5 115.8(13) . . ?
C8 C7 C6 119.5(13) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C7 C8 C9 118.4(14) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 H8 120.8 . . ?
N1 C9 C8 124.3(13) . . ?
N1 C9 H9 117.8 . . ?
C8 C9 H9 117.8 . . ?
N1 C11 C6 120.2(13) . . ?
N1 C11 C12 118.6(13) . . ?
C6 C11 C12 121.2(13) . . ?
C13 C12 C11 119.7(14) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 120.9(14) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C5 C14 C13 119.1(14) . . ?
C5 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
F4 C15 C16 120.4(12) . . ?
F4 C15 C4 116.7(12) . . ?
C16 C15 C4 122.8(12) . . ?
F3 C16 C15 118.4(12) . . ?
F3 C16 C1 120.4(12) . . ?
C15 C16 C1 121.3(12) . . ?
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
I1 C1 2.103(13) . ?
F1 C3 1.369(15) . ?
F2 C2 1.329(14) . ?
O1 C4 1.312(15) . ?
O1 C5 1.413(15) . ?
F4 C15 1.344(14) . ?
F3 C16 1.344(15) . ?
N1 C9 1.27(2) . ?
N1 C11 1.409(18) . ?
C1 C2 1.364(19) . ?
C1 C16 1.380(18) . ?
C2 C3 1.415(19) . ?
C3 C4 1.412(19) . ?
C4 C15 1.41(2) . ?
C5 C14 1.35(2) . ?
C5 C6 1.423(19) . ?
C6 C7 1.38(2) . ?
C6 C11 1.413(18) . ?
C7 C8 1.35(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.44(2) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C11 C12 1.42(2) . ?
C12 C13 1.36(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.41(2) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.378(18) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C8 H8 F3 0.95 2.65 3.382(17) 134.5 2_666 yes
C14 H14 F2 0.95 2.48 3.153(17) 127.4 2_546 yes
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
C16 C1 C2 F2 177.3(12) . . . . ?
I1 C1 C2 F2 -5.4(18) . . . . ?
C16 C1 C2 C3 -3(2) . . . . ?
I1 C1 C2 C3 174.0(10) . . . . ?
F2 C2 C3 F1 1.8(19) . . . . ?
C1 C2 C3 F1 -177.7(12) . . . . ?
F2 C2 C3 C4 179.8(13) . . . . ?
C1 C2 C3 C4 0(2) . . . . ?
C5 O1 C4 C3 -98.1(17) . . . . ?
C5 O1 C4 C15 85.0(18) . . . . ?
F1 C3 C4 O1 5(2) . . . . ?
C2 C3 C4 O1 -173.3(13) . . . . ?
F1 C3 C4 C15 -178.2(12) . . . . ?
C2 C3 C4 C15 4(2) . . . . ?
C4 O1 C5 C14 26(2) . . . . ?
C4 O1 C5 C6 -156.2(13) . . . . ?
C14 C5 C6 C7 -179.6(14) . . . . ?
O1 C5 C6 C7 2(2) . . . . ?
C14 C5 C6 C11 0(2) . . . . ?
O1 C5 C6 C11 -177.9(12) . . . . ?
C11 C6 C7 C8 0(2) . . . . ?
C5 C6 C7 C8 -179.8(14) . . . . ?
C6 C7 C8 C9 -1(2) . . . . ?
C11 N1 C9 C8 -2(2) . . . . ?
C7 C8 C9 N1 2(2) . . . . ?
C9 N1 C11 C6 2(2) . . . . ?
C9 N1 C11 C12 180.0(14) . . . . ?
C7 C6 C11 N1 -1(2) . . . . ?
C5 C6 C11 N1 179.1(13) . . . . ?
C7 C6 C11 C12 -178.9(14) . . . . ?
C5 C6 C11 C12 1(2) . . . . ?
N1 C11 C12 C13 -179.3(15) . . . . ?
C6 C11 C12 C13 -1(2) . . . . ?
C11 C12 C13 C14 0(2) . . . . ?
O1 C5 C14 C13 176.5(14) . . . . ?
C6 C5 C14 C13 -1(2) . . . . ?
C12 C13 C14 C5 1(2) . . . . ?
O1 C4 C15 F4 -4(2) . . . . ?
C3 C4 C15 F4 178.7(12) . . . . ?
O1 C4 C15 C16 171.8(14) . . . . ?
C3 C4 C15 C16 -5(2) . . . . ?
F4 C15 C16 F3 -2.7(19) . . . . ?
C4 C15 C16 F3 -178.5(13) . . . . ?
F4 C15 C16 C1 178.6(13) . . . . ?
C4 C15 C16 C1 3(2) . . . . ?
C2 C1 C16 F3 -176.9(12) . . . . ?
I1 C1 C16 F3 5.9(18) . . . . ?
C2 C1 C16 C15 2(2) . . . . ?
I1 C1 C16 C15 -175.3(10) . . . . ?
