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#$Date: 2025-11-26 23:57:50 +0100 (Wed 26 de Nov de 2025) $
#$Revision: 303439 $
#$URL: svn://www.crystallography.net/cod/cif/7/13/52/7135230.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_7135230
loop_
_publ_author_name
'Parthasarathy, Thiyagaraj'
'Bhowmik, Aritra'
'Bhattacharya, Biswajit'
'Mishra, Manish Kumar'
'Ghosh, Soumyajit'
_publ_section_title
;
 Reversible Twisting-Induced Crystalline--Polycrystalline Transformation
 in Cyanoacrylate Crystals
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D5CC05852J
_journal_year                    2025
_chemical_formula_moiety         'C12 H10 Cl N O2'
_chemical_formula_sum            'C12 H10 Cl N O2'
_chemical_formula_weight         235.66
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-11-21
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2025-11-21 deposited with the CCDC.	2025-11-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.397(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.959(4)
_cell_length_b                   5.3671(12)
_cell_length_c                   15.422(4)
_cell_measurement_reflns_used    400
_cell_measurement_temperature    300.00
_cell_measurement_theta_max      26.77
_cell_measurement_theta_min      2.65
_cell_volume                     1174.9(5)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      300.00
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.911
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16249
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.375
_diffrn_reflns_theta_min         2.784
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.309
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
'XPREP' - A PROGRAM DATA PREPARATION & RECIPROCAL 
SPACE EXPLORATION,
Bruker Analytical X-ray Systems, 1997
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       Neddle
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.121
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.029
_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     146
_refine_ls_number_reflns         2191
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0446
_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)+(0.0640P)²+0.1263P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1243
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1570
_reflns_number_total             2191
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5cc05852j8.cif
_cod_data_source_block           bb340_CCDC1
_cod_database_code               7135230
_shelxl_version_number           2013-4
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C5(H5), C6(H6), C2(H2), C3(H3)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
Cl1 Cl 0.18268(5) 0.97843(12) 0.62582(5) 0.1064(3) Uani 1 1 d . . . . .
O2 O 0.46506(10) 0.1983(2) 0.24441(8) 0.0760(4) Uani 1 1 d . . . . .
O1 O 0.50263(11) 0.0081(2) 0.37992(9) 0.0791(4) Uani 1 1 d . . . . .
N1 N 0.32250(12) 0.6743(3) 0.22477(10) 0.0778(5) Uani 1 1 d . . . . .
C8 C 0.40362(12) 0.3646(3) 0.35265(10) 0.0567(4) Uani 1 1 d . . . . .
C7 C 0.39550(12) 0.3641(3) 0.43690(10) 0.0591(4) Uani 1 1 d . . . . .
H7 H 0.4300 0.2399 0.4751 0.071 Uiso 1 1 calc R U . . .
C9 C 0.35783(13) 0.5384(3) 0.28206(11) 0.0614(4) Uani 1 1 d . . . . .
C10 C 0.46265(13) 0.1707(3) 0.32898(11) 0.0622(4) Uani 1 1 d . . . . .
C5 C 0.24292(14) 0.8723(4) 0.48315(12) 0.0727(5) Uani 1 1 d . . . . .
H5 H 0.2091 1.0120 0.4554 0.087 Uiso 1 1 calc R U . . .
C1 C 0.34237(12) 0.5232(3) 0.47874(11) 0.0579(4) Uani 1 1 d . . . . .
C4 C 0.24443(14) 0.8026(3) 0.56928(13) 0.0709(5) Uani 1 1 d . . . . .
C6 C 0.29188(14) 0.7337(3) 0.43851(11) 0.0675(5) Uani 1 1 d . . . . .
H6 H 0.2913 0.7813 0.3804 0.081 Uiso 1 1 calc R U . . .
C2 C 0.34247(15) 0.4596(4) 0.56644(11) 0.0700(5) Uani 1 1 d . . . . .
H2 H 0.3765 0.3210 0.5951 0.084 Uiso 1 1 calc R U . . .
C3 C 0.29356(16) 0.5970(4) 0.61135(12) 0.0784(6) Uani 1 1 d . . . . .
H3 H 0.2937 0.5513 0.6696 0.094 Uiso 1 1 calc R U . . .
C11 C 0.51764(18) 0.0140(4) 0.21150(14) 0.0878(6) Uani 1 1 d . . . . .
H11A H 0.5079 -0.1504 0.2330 0.105 Uiso 1 1 calc R U . . .
H11B H 0.5844 0.0517 0.2339 0.105 Uiso 1 1 calc R U . . .
C12 C 0.4840(2) 0.0211(6) 0.11207(17) 0.1275(11) Uani 1 1 d . . . . .
H12A H 0.5185 -0.0973 0.0885 0.191 Uiso 1 1 calc R U . . .
H12B H 0.4930 0.1852 0.0915 0.191 Uiso 1 1 calc R U . . .
H12C H 0.4181 -0.0199 0.0906 0.191 Uiso 1 1 calc R U . . .
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'
Cl Cl 0.1484 0.1585 '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'
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
C10 O2 C11 117.01(15) . . ?
C7 C8 C9 124.69(16) . . ?
C7 C8 C10 118.64(14) . . ?
C9 C8 C10 116.66(14) . . ?
C8 C7 H7 114.4 . . ?
C8 C7 C1 131.24(16) . . ?
C1 C7 H7 114.4 . . ?
N1 C9 C8 178.48(19) . . ?
O2 C10 C8 111.54(14) . . ?
O1 C10 O2 124.29(17) . . ?
O1 C10 C8 124.17(15) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C6 C5 C4 119.29(18) . . ?
C6 C1 C7 125.21(15) . . ?
C6 C1 C2 117.76(17) . . ?
C2 C1 C7 117.03(16) . . ?
C5 C4 Cl1 119.26(16) . . ?
C3 C4 Cl1 119.41(15) . . ?
C3 C4 C5 121.34(18) . . ?
C5 C6 C1 121.14(16) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
C1 C2 H2 119.3 . . ?
C3 C2 C1 121.40(18) . . ?
C3 C2 H2 119.3 . . ?
C4 C3 C2 119.08(17) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
O2 C11 H11A 110.2 . . ?
O2 C11 H11B 110.2 . . ?
O2 C11 C12 107.75(19) . . ?
H11A C11 H11B 108.5 . . ?
C12 C11 H11A 110.2 . . ?
C12 C11 H11B 110.2 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
Cl1 C4 1.736(2) . ?
O2 C10 1.324(2) . ?
O2 C11 1.451(2) . ?
O1 C10 1.200(2) . ?
N1 C9 1.139(2) . ?
C8 C7 1.343(2) . ?
C8 C9 1.433(2) . ?
C8 C10 1.483(2) . ?
C7 H7 0.9300 . ?
C7 C1 1.450(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.373(3) . ?
C5 C6 1.372(3) . ?
C1 C6 1.391(2) . ?
C1 C2 1.394(2) . ?
C4 C3 1.370(3) . ?
C6 H6 0.9300 . ?
C2 H2 0.9300 . ?
C2 C3 1.371(3) . ?
C3 H3 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.456(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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
Cl1 C4 C3 C2 -179.73(15) . . . . ?
C8 C7 C1 C6 -5.7(3) . . . . ?
C8 C7 C1 C2 174.59(18) . . . . ?
C7 C8 C10 O2 -178.88(16) . . . . ?
C7 C8 C10 O1 1.6(3) . . . . ?
C7 C1 C6 C5 179.47(17) . . . . ?
C7 C1 C2 C3 -179.32(16) . . . . ?
C9 C8 C7 C1 0.4(3) . . . . ?
C9 C8 C10 O2 2.1(2) . . . . ?
C9 C8 C10 O1 -177.42(17) . . . . ?
C10 O2 C11 C12 159.3(2) . . . . ?
C10 C8 C7 C1 -178.56(16) . . . . ?
C5 C4 C3 C2 0.4(3) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C4 C5 C6 C1 0.4(3) . . . . ?
C6 C5 C4 Cl1 179.86(14) . . . . ?
C6 C5 C4 C3 -0.2(3) . . . . ?
C6 C1 C2 C3 0.9(3) . . . . ?
C2 C1 C6 C5 -0.8(3) . . . . ?
C11 O2 C10 O1 1.8(3) . . . . ?
C11 O2 C10 C8 -177.67(16) . . . . ?
