#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/42/7214287.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_7214287
loop_
_publ_author_name
'Xuan, Xiao-Peng'
'Chang, Liang-Liang'
'Zhang, Heng'
'Wang, Na'
'Zhao, Yang'
_publ_section_title
;
 Hydrogen bonds in the crystal structure of hydrophobic and hydrophilic
 COOH-functionalized imidazolium ionic liquids
;
_journal_issue                   14
_journal_name_full               CrystEngComm
_journal_page_first              3040
_journal_paper_doi               10.1039/c3ce42492h
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C7 H11 Br N2 O2'
_chemical_formula_weight         235.09
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.666(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.114(5)
_cell_length_b                   17.602(13)
_cell_length_c                   8.188(6)
_cell_measurement_reflns_used    1790
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.90
_cell_measurement_theta_min      2.31
_cell_volume                     959.3(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II 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  0.0945
_diffrn_reflns_av_sigmaI/netI    0.0807
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5130
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.31
_exptl_absorpt_coefficient_mu    4.249
_exptl_absorpt_correction_T_max  0.5682
_exptl_absorpt_correction_T_min  0.4990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.807
_refine_diff_density_min         -0.875
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1872
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0501P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1134
_reflns_number_gt                1337
_reflns_number_total             1872
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce42492h2.cif
_cod_data_source_block           a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      'P2(1)/c  '
_cod_database_code               7214287
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.8265(5) 0.1156(2) 1.0493(6) 0.0842(13) Uani 1 1 d .
O2 O 1.0290(4) 0.19567(18) 0.9878(5) 0.0602(9) Uani 1 1 d .
H2 H 1.1150 0.1666 1.0494 0.090 Uiso 1 1 calc R
N1 N 0.2229(5) 0.08917(17) 0.6961(5) 0.0374(8) Uani 1 1 d .
N2 N -0.0168(5) 0.0233(2) 0.7225(5) 0.0534(10) Uani 1 1 d .
H2A H -0.0802 -0.0100 0.7601 0.064 Uiso 1 1 calc R
C1 C -0.1028(6) 0.0729(3) 0.5913(7) 0.0540(12) Uani 1 1 d .
H1 H -0.2387 0.0769 0.5249 0.065 Uiso 1 1 calc R
C2 C 0.0479(6) 0.1154(3) 0.5758(6) 0.0495(11) Uani 1 1 d .
H2B H 0.0350 0.1551 0.4977 0.059 Uiso 1 1 calc R
C3 C 0.1787(6) 0.0339(2) 0.7838(5) 0.0477(11) Uani 1 1 d .
H3 H 0.2706 0.0067 0.8745 0.057 Uiso 1 1 calc R
C4 C 0.4250(6) 0.1181(3) 0.7242(6) 0.0467(11) Uani 1 1 d .
H4A H 0.4369 0.1286 0.6119 0.056 Uiso 1 1 calc R
H4B H 0.5227 0.0793 0.7814 0.056 Uiso 1 1 calc R
C5 C 0.4727(5) 0.1890(2) 0.8329(6) 0.0435(10) Uani 1 1 d .
H5A H 0.4644 0.1784 0.9464 0.052 Uiso 1 1 calc R
H5B H 0.3741 0.2278 0.7770 0.052 Uiso 1 1 calc R
C6 C 0.6831(6) 0.2187(3) 0.8567(6) 0.0482(11) Uani 1 1 d .
H6A H 0.6976 0.2211 0.7433 0.058 Uiso 1 1 calc R
H6B H 0.6961 0.2700 0.9027 0.058 Uiso 1 1 calc R
C7 C 0.8497(6) 0.1711(2) 0.9760(6) 0.0435(10) Uani 1 1 d .
Br1 Br 0.37684(6) 0.08911(2) 0.24416(6) 0.0463(2) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0431(19) 0.085(3) 0.105(3) 0.055(2) 0.0018(19) -0.0024(18)
O2 0.0330(15) 0.0473(19) 0.088(2) 0.0174(17) 0.0060(15) -0.0031(13)
N1 0.0292(18) 0.038(2) 0.039(2) -0.0028(15) 0.0048(14) -0.0005(13)
N2 0.053(2) 0.048(2) 0.063(3) -0.013(2) 0.0241(19) -0.0208(18)
C1 0.028(2) 0.058(3) 0.066(3) -0.015(3) 0.004(2) 0.000(2)
C2 0.038(2) 0.042(2) 0.055(3) 0.007(2) 0.000(2) 0.0099(19)
C3 0.049(3) 0.039(3) 0.048(3) 0.002(2) 0.008(2) -0.0051(19)
C4 0.032(2) 0.049(3) 0.056(3) -0.011(2) 0.012(2) -0.0069(19)
C5 0.036(2) 0.028(2) 0.060(3) 0.0013(19) 0.0086(19) 0.0031(17)
C6 0.033(2) 0.039(3) 0.061(3) 0.005(2) 0.0040(19) -0.0033(18)
C7 0.036(2) 0.035(2) 0.054(3) 0.001(2) 0.0096(19) -0.0063(17)
Br1 0.0311(3) 0.0479(3) 0.0509(3) 0.0034(2) 0.00333(19) -0.00205(16)
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
C7 O2 H2 109.5
C3 N1 C2 108.2(4)
C3 N1 C4 125.7(4)
C2 N1 C4 126.1(4)
C3 N2 C1 109.4(3)
C3 N2 H2A 125.3
C1 N2 H2A 125.3
C2 C1 N2 106.4(4)
C2 C1 H1 126.8
N2 C1 H1 126.8
C1 C2 N1 107.3(4)
C1 C2 H2B 126.4
N1 C2 H2B 126.4
N1 C3 N2 108.8(4)
N1 C3 H3 125.6
N2 C3 H3 125.6
N1 C4 C5 112.7(3)
N1 C4 H4A 109.0
C5 C4 H4A 109.0
N1 C4 H4B 109.0
C5 C4 H4B 109.0
H4A C4 H4B 107.8
C4 C5 C6 111.5(3)
C4 C5 H5A 109.3
C6 C5 H5A 109.3
C4 C5 H5B 109.3
C6 C5 H5B 109.3
H5A C5 H5B 108.0
C7 C6 C5 113.9(4)
C7 C6 H6A 108.8
C5 C6 H6A 108.8
C7 C6 H6B 108.8
C5 C6 H6B 108.8
H6A C6 H6B 107.7
O1 C7 O2 122.4(4)
O1 C7 C6 124.8(4)
O2 C7 C6 112.8(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.188(5)
O2 C7 1.318(4)
O2 H2 0.8200
N1 C3 1.312(5)
N1 C2 1.367(6)
N1 C4 1.465(5)
N2 C3 1.315(5)
N2 C1 1.351(6)
N2 H2A 0.8600
C1 C2 1.349(7)
C1 H1 0.9300
C2 H2B 0.9300
C3 H3 0.9300
C4 C5 1.500(6)
C4 H4A 0.9700
C4 H4B 0.9700
C5 C6 1.532(5)
C5 H5A 0.9700
C5 H5B 0.9700
C6 C7 1.498(6)
C6 H6A 0.9700
C6 H6B 0.9700
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
O2 H2 Br1 0.82 2.40 3.222(3) 175.8 1_656
N2 H2A Br1 0.86 2.52 3.323(4) 156.1 3_556
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
C3 N2 C1 C2 -0.9(5)
N2 C1 C2 N1 1.3(5)
C3 N1 C2 C1 -1.4(5)
C4 N1 C2 C1 179.3(4)
C2 N1 C3 N2 0.8(5)
C4 N1 C3 N2 -179.8(3)
C1 N2 C3 N1 0.0(5)
C3 N1 C4 C5 -98.8(5)
C2 N1 C4 C5 80.5(5)
N1 C4 C5 C6 -178.8(3)
C4 C5 C6 C7 -71.9(5)
C5 C6 C7 O1 -0.9(7)
C5 C6 C7 O2 176.9(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139198091
