#------------------------------------------------------------------------------
#$Date: 2026-04-06 23:55:50 +0200 (Mon 06 de Apr de 2026) $
#$Revision: 305455 $
#$URL: svn://www.crystallography.net/cod/cif/7/13/57/7135709.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_7135709
loop_
_publ_author_name
'Parthasarathy, Thiyagaraj'
'Bhowmik, Aritra'
'Mishra, Manish Kumar'
'Ghosh, Soumyajit'
_publ_section_title
;
 Helically Twistable Cyanoacrylate Crystal with Simultaneous
 Photomechanical Bending
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D6CC00942E
_journal_year                    2026
_chemical_formula_moiety         'C13 H12 Br N O3'
_chemical_formula_sum            'C13 H12 Br N O3'
_chemical_formula_weight         310.15
_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
_audit_creation_date             2025-05-22
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2026-02-04 deposited with the CCDC.	2026-04-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.943(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5620(7)
_cell_length_b                   4.0956(2)
_cell_length_c                   27.5269(15)
_cell_measurement_reflns_used    6603
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.67
_cell_measurement_theta_min      2.98
_cell_volume                     1296.48(12)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200.00
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0763
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            19873
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.373
_diffrn_reflns_theta_min         2.702
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.170
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5448
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1517 before and 0.0861 after correction.
The Ratio of minimum to maximum transmission is 0.7306.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_description       Needle
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.7
_exptl_crystal_size_min          0.6
_refine_diff_density_max         0.582
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         3231
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.131
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0348
_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)+(0.0339P)²+0.7051P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0961
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2572
_reflns_number_total             3231
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d6cc00942e9.cif
_cod_data_source_block           TP34
_cod_database_code               7135709
_shelx_shelxl_version_number     2019/3
_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:
 C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C6(H6), C10(H10)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C13(H13A,H13B,H13C)
;
_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
Br1 Br 0.72999(2) 0.78220(7) 0.30303(2) 0.02841(11) Uani 1 1 d . . . . .
N1 N 0.6795(2) 0.1800(6) 0.57750(9) 0.0358(6) Uani 1 1 d . . . . .
O1 O 0.90532(16) 0.6181(5) 0.62151(6) 0.0269(4) Uani 1 1 d . . . . .
C1 C 0.9188(2) 0.6992(6) 0.57548(10) 0.0248(5) Uani 1 1 d . . . . .
O2 O 0.99413(17) 0.8783(6) 0.56393(7) 0.0367(5) Uani 1 1 d . . . . .
C2 C 0.8278(2) 0.5510(6) 0.54025(9) 0.0220(5) Uani 1 1 d . . . . .
C3 C 0.7438(2) 0.3462(6) 0.56064(9) 0.0247(5) Uani 1 1 d . . . . .
O3 O 0.51708(16) 0.4207(5) 0.32382(6) 0.0287(4) Uani 1 1 d . . . . .
C4 C 0.8256(2) 0.6259(6) 0.49247(9) 0.0235(5) Uani 1 1 d . . . . .
H4 H 0.889552 0.754420 0.484718 0.028 Uiso 1 1 calc R U . . .
C5 C 0.7433(2) 0.5461(6) 0.45071(9) 0.0227(5) Uani 1 1 d . . . . .
C8 C 0.5876(2) 0.4481(6) 0.36607(9) 0.0233(5) Uani 1 1 d . . . . .
C7 C 0.5630(2) 0.3253(6) 0.41106(10) 0.0264(5) Uani 1 1 d . . . . .
H7 H 0.493092 0.206646 0.413246 0.032 Uiso 1 1 calc R U . . .
C6 C 0.6388(2) 0.3741(7) 0.45244(9) 0.0266(5) Uani 1 1 d . . . . .
H6 H 0.619958 0.289562 0.482781 0.032 Uiso 1 1 calc R U . . .
C9 C 0.6927(2) 0.6139(6) 0.36377(9) 0.0219(5) Uani 1 1 d . . . . .
C10 C 0.7688(2) 0.6649(6) 0.40515(9) 0.0230(5) Uani 1 1 d . . . . .
H10 H 0.839101 0.781295 0.402776 0.028 Uiso 1 1 calc R U . . .
C11 C 0.9446(4) 0.6988(8) 0.70749(12) 0.0472(9) Uani 1 1 d . . . . .
H11A H 0.866495 0.789109 0.708848 0.071 Uiso 1 1 calc R U . . .
H11B H 0.998085 0.796018 0.733456 0.071 Uiso 1 1 calc R U . . .
H11C H 0.942389 0.461590 0.711991 0.071 Uiso 1 1 calc R U . . .
C12 C 0.9857(3) 0.7749(7) 0.65872(10) 0.0308(6) Uani 1 1 d . . . . .
H12A H 0.986366 1.013930 0.653393 0.037 Uiso 1 1 calc R U . . .
H12B H 1.065444 0.690433 0.657261 0.037 Uiso 1 1 calc R U . . .
C13 C 0.4091(3) 0.2521(7) 0.32562(12) 0.0341(7) Uani 1 1 d . . . . .
H13A H 0.365477 0.253858 0.293143 0.051 Uiso 1 1 calc R U . . .
H13B H 0.363479 0.361229 0.348949 0.051 Uiso 1 1 calc R U . . .
H13C H 0.424460 0.026013 0.336001 0.051 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'
Br Br -0.2901 2.4595 '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
C1 O1 C12 115.4(2) . . ?
O1 C1 C2 111.9(2) . . ?
O2 C1 O1 124.1(2) . . ?
O2 C1 C2 124.0(2) . . ?
C3 C2 C1 116.4(2) . . ?
C4 C2 C1 119.0(2) . . ?
C4 C2 C3 124.6(2) . . ?
N1 C3 C2 178.3(3) . . ?
C8 O3 C13 117.4(2) . . ?
C2 C4 H4 114.1 . . ?
C2 C4 C5 131.8(2) . . ?
C5 C4 H4 114.1 . . ?
C6 C5 C4 125.6(2) . . ?
C6 C5 C10 117.7(2) . . ?
C10 C5 C4 116.6(2) . . ?
O3 C8 C7 125.0(2) . . ?
O3 C8 C9 116.8(2) . . ?
C7 C8 C9 118.3(2) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 C8 120.7(2) . . ?
C6 C7 H7 119.6 . . ?
C5 C6 H6 119.3 . . ?
C7 C6 C5 121.4(2) . . ?
C7 C6 H6 119.3 . . ?
C8 C9 Br1 119.55(18) . . ?
C10 C9 Br1 119.22(19) . . ?
C10 C9 C8 121.2(2) . . ?
C5 C10 H10 119.7 . . ?
C9 C10 C5 120.6(2) . . ?
C9 C10 H10 119.7 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
C12 C11 H11C 109.5 . . ?
O1 C12 C11 107.4(2) . . ?
O1 C12 H12A 110.2 . . ?
O1 C12 H12B 110.2 . . ?
C11 C12 H12A 110.2 . . ?
C11 C12 H12B 110.2 . . ?
H12A C12 H12B 108.5 . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
Br1 C9 1.899(2) . ?
N1 C3 1.141(4) . ?
O1 C1 1.335(3) . ?
O1 C12 1.459(3) . ?
C1 O2 1.206(3) . ?
C1 C2 1.485(4) . ?
C2 C3 1.440(4) . ?
C2 C4 1.348(3) . ?
O3 C8 1.354(3) . ?
O3 C13 1.432(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.451(3) . ?
C5 C6 1.404(4) . ?
C5 C10 1.405(3) . ?
C8 C7 1.393(4) . ?
C8 C9 1.400(3) . ?
C7 H7 0.9500 . ?
C7 C6 1.378(4) . ?
C6 H6 0.9500 . ?
C9 C10 1.381(4) . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C11 C12 1.502(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
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
Br1 C9 C10 C5 179.42(18) . . . . ?
O1 C1 C2 C3 -1.1(3) . . . . ?
O1 C1 C2 C4 176.1(2) . . . . ?
C1 O1 C12 C11 170.7(2) . . . . ?
C1 C2 C4 C5 -173.7(3) . . . . ?
O2 C1 C2 C3 -179.2(3) . . . . ?
O2 C1 C2 C4 -2.1(4) . . . . ?
C2 C4 C5 C6 3.4(5) . . . . ?
C2 C4 C5 C10 -179.6(3) . . . . ?
C3 C2 C4 C5 3.2(5) . . . . ?
O3 C8 C7 C6 -178.0(2) . . . . ?
O3 C8 C9 Br1 -0.6(3) . . . . ?
O3 C8 C9 C10 177.7(2) . . . . ?
C4 C5 C6 C7 176.4(3) . . . . ?
C4 C5 C10 C9 -176.9(2) . . . . ?
C8 C7 C6 C5 -0.5(4) . . . . ?
C8 C9 C10 C5 1.0(4) . . . . ?
C7 C8 C9 Br1 179.57(19) . . . . ?
C7 C8 C9 C10 -2.1(4) . . . . ?
C6 C5 C10 C9 0.3(4) . . . . ?
C9 C8 C7 C6 1.8(4) . . . . ?
C10 C5 C6 C7 -0.6(4) . . . . ?
C12 O1 C1 O2 2.9(4) . . . . ?
C12 O1 C1 C2 -175.2(2) . . . . ?
C13 O3 C8 C7 -0.1(4) . . . . ?
C13 O3 C8 C9 -179.9(2) . . . . ?
