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#$Date: 2023-07-05 13:29:36 +0300 (Wed, 05 Jul 2023) $
#$Revision: 284930 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/24/7062496.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_7062496
loop_
_publ_author_name
'Dahiwadkar, Rahul'
'Dubey, Gurudutt'
'Shaik, Althaf'
'Jana, Palash'
'Thiruvenkatam, Vijay'
'Kanvah, Sriram'
_publ_section_title
;
 Halogen-bonded co-crystals with AIE-active α-cyanostilbenes
;
_journal_issue                   24
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              11685
_journal_page_last               11696
_journal_paper_doi               10.1039/D3NJ00333G
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C17 H15 I N2'
_chemical_formula_sum            'C17 H15 I N2'
_chemical_formula_weight         374.21
_chemical_name_systematic        Monoiodo_diarylcyanostilbene
_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     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2d45zq
_audit_creation_date             2022-09-21
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-09-21 deposited with the CCDC.	2023-05-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.1290(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3563(4)
_cell_length_b                   6.0912(2)
_cell_length_c                   22.4406(10)
_cell_measurement_reflns_used    9995
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      56.509
_cell_measurement_theta_min      4.777
_cell_volume                     1536.70(10)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            27580
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.305
_diffrn_reflns_theta_min         1.811
_exptl_absorpt_coefficient_mu    2.076
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5704
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2- Bruker AXS area detector scaling and absorption correction.'
_exptl_crystal_colour            'clear greenish green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_description       plate
_exptl_crystal_F_000             736
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.333
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.119
_refine_diff_density_max         0.663
_refine_diff_density_min         -0.744
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3737
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0338
_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)+(0.0444P)²+0.8310P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.0957
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3242
_reflns_number_total             3737
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj00333g2.cif
_cod_data_source_block           monoiodo_0m_a
_cod_depositor_comments
'Adding full bibliography for 7062496--7062498.cif.'
_cod_database_code               7062496
_shelx_shelxl_version_number     2019/2
_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_max   0.790
_shelx_estimated_absorpt_t_min   0.545
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C14(H14), C9(H9), C12(H12), C3(H3), C15(H15), C2(H2), C5(H5), C6(H6)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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 0.17545(2) 0.56079(4) 0.51237(2) 0.07726(12) Uani 1 1 d . . . . .
N2 N 0.9575(2) 0.4081(3) 0.15076(10) 0.0572(5) Uani 1 1 d . . . . .
C13 C 0.8737(2) 0.4147(4) 0.18850(10) 0.0465(5) Uani 1 1 d . . . . .
C10 C 0.6986(2) 0.4238(4) 0.26853(10) 0.0469(5) Uani 1 1 d . . . . .
C7 C 0.57522(18) 0.3196(4) 0.35098(10) 0.0459(4) Uani 1 1 d . . . . .
C4 C 0.48325(18) 0.3787(4) 0.38911(10) 0.0448(4) Uani 1 1 d . . . . .
C11 C 0.7792(2) 0.2504(4) 0.26836(12) 0.0546(5) Uani 1 1 d . . . . .
H11 H 0.775388 0.134460 0.294989 0.065 Uiso 1 1 calc R U . . .
C14 C 0.7929(2) 0.5899(4) 0.18834(12) 0.0540(5) Uani 1 1 d . . . . .
H14 H 0.796115 0.705563 0.161568 0.065 Uiso 1 1 calc R U . . .
C1 C 0.3097(2) 0.4840(4) 0.46059(11) 0.0515(5) Uani 1 1 d . . . . .
C9 C 0.6087(2) 0.4490(4) 0.30800(11) 0.0496(5) Uani 1 1 d . . . . .
H9 H 0.566211 0.579685 0.302431 0.059 Uiso 1 1 calc R U . . .
C12 C 0.8638(2) 0.2452(4) 0.23015(11) 0.0535(5) Uani 1 1 d . . . . .
H12 H 0.915874 0.126778 0.231901 0.064 Uiso 1 1 calc R U . . .
C3 C 0.4579(2) 0.2406(4) 0.43466(13) 0.0601(6) Uani 1 1 d . . . . .
H3 H 0.499941 0.109814 0.441409 0.072 Uiso 1 1 calc R U . . .
C15 C 0.7094(2) 0.5930(4) 0.22705(11) 0.0530(5) Uani 1 1 d . . . . .
H15 H 0.657770 0.712079 0.225763 0.064 Uiso 1 1 calc R U . . .
C2 C 0.3716(2) 0.2918(5) 0.47057(12) 0.0636(6) Uani 1 1 d . . . . .
H2 H 0.356137 0.196774 0.500955 0.076 Uiso 1 1 calc R U . . .
C5 C 0.4183(2) 0.5727(4) 0.38049(13) 0.0577(6) Uani 1 1 d . . . . .
H5 H 0.432937 0.668507 0.350113 0.069 Uiso 1 1 calc R U . . .
C6 C 0.3329(2) 0.6259(5) 0.41593(12) 0.0591(6) Uani 1 1 d . . . . .
H6 H 0.291079 0.757095 0.409718 0.071 Uiso 1 1 calc R U . . .
C16 C 1.0402(3) 0.2283(5) 0.15181(14) 0.0695(7) Uani 1 1 d . . . . .
H16A H 1.078700 0.205710 0.192252 0.104 Uiso 1 1 calc R U . . .
H16B H 1.098752 0.261833 0.126253 0.104 Uiso 1 1 calc R U . . .
H16C H 0.998098 0.097408 0.137642 0.104 Uiso 1 1 calc R U . . .
C8 C 0.6295(3) 0.1085(4) 0.36409(15) 0.0629(7) Uani 1 1 d . . . . .
C17 C 0.9639(3) 0.5741(5) 0.10568(16) 0.0717(8) Uani 1 1 d . . . . .
H17A H 0.887027 0.591920 0.082188 0.108 Uiso 1 1 calc R U . . .
H17B H 1.020353 0.530378 0.079903 0.108 Uiso 1 1 calc R U . . .
H17C H 0.988552 0.710564 0.124896 0.108 Uiso 1 1 calc R U . . .
N1 N 0.6699(4) -0.0606(4) 0.3759(2) 0.0986(12) 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'
I I -0.4742 1.8119 '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'
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
C13 N2 C16 121.6(2) . . ?
C13 N2 C17 121.7(2) . . ?
C17 N2 C16 116.6(2) . . ?
N2 C13 C14 122.3(2) . . ?
N2 C13 C12 121.3(2) . . ?
C14 C13 C12 116.4(2) . . ?
C11 C10 C9 126.8(2) . . ?
C11 C10 C15 115.8(2) . . ?
C15 C10 C9 117.4(2) . . ?
C9 C7 C4 124.4(2) . . ?
C9 C7 C8 121.0(2) . . ?
C8 C7 C4 114.5(2) . . ?
C3 C4 C7 120.9(2) . . ?
C3 C4 C5 117.2(2) . . ?
C5 C4 C7 121.9(2) . . ?
C10 C11 H11 118.9 . . ?
C12 C11 C10 122.3(2) . . ?
C12 C11 H11 118.9 . . ?
C13 C14 H14 119.4 . . ?
C15 C14 C13 121.1(2) . . ?
C15 C14 H14 119.4 . . ?
C2 C1 I1 119.84(19) . . ?
C2 C1 C6 120.6(2) . . ?
C6 C1 I1 119.51(19) . . ?
C10 C9 H9 113.9 . . ?
C7 C9 C10 132.2(2) . . ?
C7 C9 H9 113.9 . . ?
C13 C12 H12 119.2 . . ?
C11 C12 C13 121.7(2) . . ?
C11 C12 H12 119.2 . . ?
C4 C3 H3 119.0 . . ?
C4 C3 C2 121.9(2) . . ?
C2 C3 H3 119.0 . . ?
C10 C15 H15 118.6 . . ?
C14 C15 C10 122.7(2) . . ?
C14 C15 H15 118.6 . . ?
C1 C2 C3 119.1(2) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.5(2) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 119.7(2) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C8 C7 177.6(3) . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
N2 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
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 2.096(2) . ?
N2 C13 1.361(3) . ?
N2 C16 1.441(4) . ?
N2 C17 1.439(3) . ?
C13 C14 1.407(3) . ?
C13 C12 1.408(3) . ?
C10 C11 1.397(3) . ?
C10 C9 1.452(3) . ?
C10 C15 1.406(3) . ?
C7 C4 1.485(3) . ?
C7 C9 1.342(3) . ?
C7 C8 1.438(3) . ?
C4 C3 1.385(3) . ?
C4 C5 1.392(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.376(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.374(4) . ?
C1 C2 1.367(4) . ?
C1 C6 1.377(4) . ?
C9 H9 0.9300 . ?
C12 H12 0.9300 . ?
C3 H3 0.9300 . ?
C3 C2 1.390(4) . ?
C15 H15 0.9300 . ?
C2 H2 0.9300 . ?
C5 H5 0.9300 . ?
C5 C6 1.377(4) . ?
C6 H6 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C8 N1 1.143(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
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
I1 C1 C2 C3 178.2(2) . . . . ?
I1 C1 C6 C5 -177.9(2) . . . . ?
N2 C13 C14 C15 -179.8(2) . . . . ?
N2 C13 C12 C11 -179.8(3) . . . . ?
C13 C14 C15 C10 -0.3(4) . . . . ?
C10 C11 C12 C13 -0.5(4) . . . . ?
C7 C4 C3 C2 -179.5(2) . . . . ?
C7 C4 C5 C6 179.8(2) . . . . ?
C4 C7 C9 C10 177.2(2) . . . . ?
C4 C3 C2 C1 0.1(4) . . . . ?
C4 C5 C6 C1 -0.7(4) . . . . ?
C11 C10 C9 C7 -3.0(4) . . . . ?
C11 C10 C15 C14 0.3(4) . . . . ?
C14 C13 C12 C11 0.4(4) . . . . ?
C9 C10 C11 C12 -177.9(3) . . . . ?
C9 C10 C15 C14 178.5(2) . . . . ?
C9 C7 C4 C3 -176.7(2) . . . . ?
C9 C7 C4 C5 3.9(4) . . . . ?
C12 C13 C14 C15 0.0(4) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
C15 C10 C11 C12 0.1(4) . . . . ?
C15 C10 C9 C7 179.0(3) . . . . ?
C2 C1 C6 C5 0.8(4) . . . . ?
C5 C4 C3 C2 0.0(4) . . . . ?
C6 C1 C2 C3 -0.5(4) . . . . ?
C16 N2 C13 C14 179.5(3) . . . . ?
C16 N2 C13 C12 -0.2(4) . . . . ?
C8 C7 C4 C3 2.4(3) . . . . ?
C8 C7 C4 C5 -177.0(2) . . . . ?
C8 C7 C9 C10 -1.9(4) . . . . ?
C17 N2 C13 C14 -3.9(4) . . . . ?
C17 N2 C13 C12 176.4(3) . . . . ?
