#------------------------------------------------------------------------------
#$Date: 2022-03-03 03:49:29 +0200 (Thu, 03 Mar 2022) $
#$Revision: 273215 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/45/7244547.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_7244547
loop_
_publ_author_name
'Koutsoukos, Spyridon'
'Philippi, Frederik'
'Rauber, Daniel'
'Pugh, David'
'Kay, Christopher William Michael'
'Welton, Tom'
_publ_section_title
;
 Effect of the cation structure on the properties of homobaric imidazolium
 ionic liquids
;
_journal_name_full               'Physical Chemistry Chemical Physics'
_journal_paper_doi               10.1039/D1CP05169E
_journal_year                    2022
_chemical_formula_moiety         'C8 H11 N2, Br'
_chemical_formula_sum            'C8 H11 Br N2'
_chemical_formula_weight         215.10
_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             2021-06-23
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2021-11-03 deposited with the CCDC.	2022-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.618(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4022(7)
_cell_length_b                   7.5130(5)
_cell_length_c                   11.8190(9)
_cell_measurement_reflns_used    1921
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      28.0710
_cell_measurement_theta_min      3.3130
_cell_volume                     901.37(11)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0382
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.875
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -39.00  52.00   1.00    1.00    --  -13.33  77.00 120.00   91
  2  ω    -80.00  12.00   1.00    1.00    --  -13.33 -77.00   0.00   92
  3  ω     -2.00  81.00   1.00    1.00    --   14.58  57.00 -90.00   83
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0036360000
_diffrn_orient_matrix_UB_12      -0.0246032000
_diffrn_orient_matrix_UB_13      0.0571580000
_diffrn_orient_matrix_UB_21      0.0049758000
_diffrn_orient_matrix_UB_22      -0.0909471000
_diffrn_orient_matrix_UB_23      -0.0145084000
_diffrn_orient_matrix_UB_31      0.0696110000
_diffrn_orient_matrix_UB_32      0.0052161000
_diffrn_orient_matrix_UB_33      0.0176158000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.875
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4911
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.875
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.945
_diffrn_reflns_theta_min         2.949
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.499
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56029
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       0.117(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     103
_refine_ls_number_reflns         1890
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0243
_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)+(0.0212P)²+0.1512P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0484
_refine_ls_wR_factor_ref         0.0511
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1622
_reflns_number_total             1890
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cp05169e5.cif
_cod_data_source_block           '[HCC2C1C1im]Br'
_cod_database_code               7244547
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C7 H9 Br N2'
_chemical_oxdiff_usercomment     SK86_EtOH
_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   0.614
_shelx_estimated_absorpt_t_min   0.515
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_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:
 C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C8(H8A,H8B,H8C)
2.d :
 C7(H7)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.511
_oxdiff_exptl_absorpt_empirical_full_min 0.815
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
N1 N 0.52039(17) 0.3033(2) 0.93297(14) 0.0201(4) Uani 1 1 d . . . . .
C1 C 0.4051(2) 0.2247(3) 0.9656(2) 0.0284(5) Uani 1 1 d . . . . .
H1A H 0.334846 0.310204 0.953715 0.043 Uiso 1 1 calc R U . . .
H1B H 0.427306 0.190765 1.045807 0.043 Uiso 1 1 calc R U . . .
H1C H 0.377425 0.121519 0.918656 0.043 Uiso 1 1 calc R U . . .
N2 N 0.64417(17) 0.4302(2) 0.83266(15) 0.0189(4) Uani 1 1 d . . . . .
C2 C 0.5193(2) 0.3869(2) 0.83314(18) 0.0175(5) Uani 1 1 d . . . . .
C3 C 0.6486(2) 0.2933(3) 0.99688(19) 0.0274(5) Uani 1 1 d . . . . .
H3 H 0.675921 0.241869 1.069744 0.033 Uiso 1 1 calc R U . . .
C4 C 0.7261(2) 0.3712(3) 0.9348(2) 0.0261(5) Uani 1 1 d . . . . .
H4 H 0.817148 0.383502 0.955874 0.031 Uiso 1 1 calc R U . . .
C5 C 0.6864(2) 0.5226(3) 0.7375(2) 0.0229(5) Uani 1 1 d . . . . .
H5A H 0.642018 0.636656 0.724020 0.027 Uiso 1 1 calc R U . . .
H5B H 0.780450 0.544494 0.759037 0.027 Uiso 1 1 calc R U . . .
C6 C 0.6561(2) 0.4169(3) 0.6306(2) 0.0228(5) Uani 1 1 d . . . . .
C7 C 0.6251(2) 0.3303(3) 0.5466(2) 0.0290(5) Uani 1 1 d . . . . .
H7 H 0.600492 0.261490 0.479991 0.035 Uiso 1 1 calc R U . . .
C8 C 0.4022(2) 0.4246(3) 0.74020(19) 0.0234(5) Uani 1 1 d . . . . .
H8A H 0.398976 0.342130 0.677597 0.035 Uiso 1 1 calc R U . . .
H8B H 0.407495 0.543834 0.712403 0.035 Uiso 1 1 calc R U . . .
H8C H 0.324068 0.412256 0.770279 0.035 Uiso 1 1 calc R U . . .
Br1 Br 0.45629(2) -0.06844(3) 0.71839(2) 0.02436(11) 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'
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'
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
C2 N1 C1 125.06(18) . . ?
C2 N1 C3 109.19(18) . . ?
C3 N1 C1 125.63(19) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 N2 C4 109.27(18) . . ?
C2 N2 C5 124.76(17) . . ?
C4 N2 C5 125.96(18) . . ?
N1 C2 N2 107.29(17) . . ?
N1 C2 C8 126.4(2) . . ?
N2 C2 C8 126.34(19) . . ?
N1 C3 H3 126.2 . . ?
C4 C3 N1 107.53(19) . . ?
C4 C3 H3 126.2 . . ?
N2 C4 H4 126.6 . . ?
C3 C4 N2 106.71(19) . . ?
C3 C4 H4 126.6 . . ?
N2 C5 H5A 109.4 . . ?
N2 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C6 C5 N2 111.11(17) . . ?
C6 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
C7 C6 C5 176.1(2) . . ?
C6 C7 H7 180.0 . . ?
C2 C8 H8A 109.5 . . ?
C2 C8 H8B 109.5 . . ?
C2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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
N1 C1 1.462(3) . ?
N1 C2 1.335(3) . ?
N1 C3 1.384(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
N2 C2 1.340(3) . ?
N2 C4 1.389(3) . ?
N2 C5 1.468(3) . ?
C2 C8 1.479(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.338(3) . ?
C4 H4 0.9300 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.467(3) . ?
C6 C7 1.171(3) . ?
C7 H7 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 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
N1 C3 C4 N2 0.4(2) . . . . ?
C1 N1 C2 N2 -176.36(17) . . . . ?
C1 N1 C2 C8 3.5(3) . . . . ?
C1 N1 C3 C4 176.03(18) . . . . ?
C2 N1 C3 C4 -0.3(2) . . . . ?
C2 N2 C4 C3 -0.5(2) . . . . ?
C2 N2 C5 C6 -62.1(2) . . . . ?
C3 N1 C2 N2 -0.1(2) . . . . ?
C3 N1 C2 C8 179.85(19) . . . . ?
C4 N2 C2 N1 0.3(2) . . . . ?
C4 N2 C2 C8 -179.57(19) . . . . ?
C4 N2 C5 C6 116.7(2) . . . . ?
C5 N2 C2 N1 179.32(17) . . . . ?
C5 N2 C2 C8 -0.6(3) . . . . ?
C5 N2 C4 C3 -179.46(18) . . . . ?
