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#$Date: 2025-08-21 23:04:39 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301851 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/73/7057379.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_7057379
loop_
_publ_author_name
'Gamekkanda, Janaka C.'
'Sinha, Abhijeet S.'
'Desper, John'
'Đaković, Marijana'
'Aakeröy, Christer B.'
_publ_section_title
;
 Competition between hydrogen bonds and halogen bonds: a structural study
;
_journal_issue                   13
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              10539
_journal_paper_doi               10.1039/C8NJ00537K
_journal_volume                  42
_journal_year                    2018
_chemical_formula_moiety         'C12 H12 N2, C10 H12 O2'
_chemical_formula_sum            'C22 H24 N2 O2'
_chemical_formula_weight         348.43
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2018-01-29 deposited with the CCDC.
2018-04-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.559(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.5202(15)
_cell_length_b                   7.7849(10)
_cell_length_c                   11.8577(16)
_cell_measurement_reflns_used    3358
_cell_measurement_temperature    228.(2)
_cell_measurement_theta_max      28.07
_cell_measurement_theta_min      3.23
_cell_volume                     967.2(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      228.(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  Graphite
_diffrn_radiation_source         'Fine-focus sealed tube'
_diffrn_radiation_type           Mok\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9913
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         3.23
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Irregular
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.280
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         2395
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0457
_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)+(0.0474P)²+0.2847P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1210
_reflns_number_gt                1878
_reflns_number_total             2395
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8nj00537k2.cif
_cod_data_source_block           D3A5
_cod_depositor_comments
'Adding full bibliography for 7057378--7057386.cif.'
_cod_database_code               7057379
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_posn
_atom_site_occupancy
C C1 0.43914(12) 0.77159(16) 0.50891(12) 0.0337(3) Uani d . . 1
C C2 0.38734(13) 0.71513(17) 0.58890(13) 0.0372(3) Uani d . . 1
H H2 0.4081 0.7707 0.6652 0.045 Uiso calc U R 1
C C3 0.30485(13) 0.57643(18) 0.55573(14) 0.0396(3) Uani d . . 1
H H3 0.2714 0.5394 0.6116 0.048 Uiso calc U R 1
N N4 0.27034(11) 0.49259(15) 0.44883(11) 0.0405(3) Uani d . . 1
C C5 0.32048(14) 0.54729(18) 0.37218(13) 0.0419(3) Uani d . . 1
H H5 0.2975 0.4897 0.2963 0.05 Uiso calc U R 1
C C6 0.40433(13) 0.68382(18) 0.39785(13) 0.0396(3) Uani d . . 1
H H6 0.4374 0.7168 0.3407 0.048 Uiso calc U R 1
C C7 0.52951(13) 0.92226(18) 0.54145(14) 0.0412(3) Uani d . . 1
H H7A 0.6074 0.8884 0.533 0.049 Uiso calc U R 1
H H7B 0.5533 0.9543 0.6282 0.049 Uiso calc U R 1
C C8 0.07678(12) 0.13624(18) 0.47256(11) 0.0354(3) Uani d . . 1
C C9 0.05512(13) -0.0415(2) 0.41255(12) 0.0394(3) Uani d . . 1
H H9A -0.0191 -0.0371 0.3324 0.047 Uiso calc U R 1
H H9B 0.1296 -0.073 0.3971 0.047 Uiso calc U R 1
C C10 0.03325(12) -0.17855(18) 0.49249(13) 0.0393(3) Uani d . . 1
H H10A 0.1115 -0.1927 0.5684 0.047 Uiso calc U R 1
H H10B 0.0155 -0.2881 0.4478 0.047 Uiso calc U R 1
C C11 0.20012(12) 0.14111(18) 0.58426(12) 0.0355(3) Uani d . . 1
C C12 0.29834(13) 0.14640(19) 0.67239(13) 0.0410(3) Uani d . . 1
H H12 0.3766 0.1506 0.7426 0.049 Uiso calc U R 1
H H13 0.146(2) 0.330(3) 0.412(2) 0.081(6) Uiso d . . 1
O O13 0.07775(11) 0.25676(17) 0.38224(10) 0.0639(4) Uani d . . 1
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C2 C1 C6 . . 117.19(12)
C2 C1 C7 . . 121.30(13)
C6 C1 C7 . . 121.50(12)
C3 C2 C1 . . 119.57(13)
C3 C2 H2 . . 120.2
C1 C2 H2 . . 120.2
N4 C3 C2 . . 123.48(13)
N4 C3 H3 . . 118.3
C2 C3 H3 . . 118.3
C3 N4 C5 . . 116.74(12)
N4 C5 C6 . . 123.82(13)
N4 C5 H5 . . 118.1
C6 C5 H5 . . 118.1
C5 C6 C1 . . 119.19(13)
C5 C6 H6 . . 120.4
C1 C6 H6 . . 120.4
C1 C7 C7 . 3_676 112.08(14)
C1 C7 H7A . . 109.2
C7 C7 H7A 3_676 . 109.2
C1 C7 H7B . . 109.2
C7 C7 H7B 3_676 . 109.2
H7A C7 H7B . . 107.9
O13 C8 C11 . . 110.43(10)
O13 C8 C10 . 3_556 109.19(12)
C11 C8 C10 . 3_556 110.31(11)
O13 C8 C9 . . 107.25(11)
C11 C8 C9 . . 110.39(12)
C10 C8 C9 3_556 . 109.21(10)
C10 C9 C8 . . 112.53(11)
C10 C9 H9A . . 109.1
C8 C9 H9A . . 109.1
C10 C9 H9B . . 109.1
C8 C9 H9B . . 109.1
H9A C9 H9B . . 107.8
C9 C10 C8 . 3_556 113.02(11)
C9 C10 H10A . . 109.0
C8 C10 H10A 3_556 . 109.0
C9 C10 H10B . . 109.0
C8 C10 H10B 3_556 . 109.0
H10A C10 H10B . . 107.8
C12 C11 C8 . . 179.32(15)
C11 C12 H12 . . 180.0
C8 O13 H13 . . 113.0(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.3854(19)
C1 C6 . 1.387(2)
C1 C7 . 1.5082(18)
C2 C3 . 1.3831(19)
C2 H2 . 0.94
C3 N4 . 1.3310(19)
C3 H3 . 0.94
N4 C5 . 1.3333(18)
C5 C6 . 1.382(2)
C5 H5 . 0.94
C6 H6 . 0.94
C7 C7 3_676 1.529(3)
C7 H7A . 0.98
C7 H7B . 0.98
C8 O13 . 1.4274(15)
C8 C11 . 1.4867(17)
C8 C10 3_556 1.524(2)
C8 C9 . 1.529(2)
C9 C10 . 1.516(2)
C9 H9A . 0.98
C9 H9B . 0.98
C10 C8 3_556 1.524(2)
C10 H10A . 0.98
C10 H10B . 0.98
C11 C12 . 1.1795(18)
C12 H12 . 0.94
O13 H13 . 0.92(2)
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
O13 H13 N4 0.92(2) 1.82(2) 2.7314(16) 171.(2)
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
C6 C1 C2 C3 . . 0.06(19)
C7 C1 C2 C3 . . -179.98(12)
C1 C2 C3 N4 . . -0.6(2)
C2 C3 N4 C5 . . 0.6(2)
C3 N4 C5 C6 . . -0.1(2)
N4 C5 C6 C1 . . -0.4(2)
C2 C1 C6 C5 . . 0.4(2)
C7 C1 C6 C5 . . -179.56(13)
C2 C1 C7 C7 . 3_676 -111.72(18)
C6 C1 C7 C7 . 3_676 68.2(2)
O13 C8 C9 C10 . . -171.84(11)
C11 C8 C9 C10 . . 67.81(14)
C10 C8 C9 C10 3_556 . -53.64(15)
C8 C9 C10 C8 . 3_556 55.71(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139178603
