#------------------------------------------------------------------------------
#$Date: 2022-03-03 03:49:29 +0200 (Thu, 03 Mar 2022) $
#$Revision: 273215 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/45/7244548.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_7244548
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         'C7 H10 N3, Br'
_chemical_formula_sum            'C7 H10 Br N3'
_chemical_formula_weight         216.09
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 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                 94.909(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.0482(3)
_cell_length_b                   11.4371(5)
_cell_length_c                   11.1712(6)
_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                     897.22(7)
_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 1.000
_diffrn_measured_fraction_theta_max 0.926
_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  0.0354
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5531
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.867
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.153
_diffrn_reflns_theta_min         3.404
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.523
_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    1.600
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
;
 Flack x determined using 776 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.007(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1904
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0330
_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)+(0.0322P)²+1.1065P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0703
_refine_ls_wR_factor_ref         0.0720
_reflns_Friedel_coverage         0.868
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.809
_reflns_number_gt                1782
_reflns_number_total             1904
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cp05169e5.cif
_cod_data_source_block           '[NC2C1C1im]Br'
_cod_database_code               7244548
_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   0.550
_shelx_estimated_absorpt_t_min   0.465
_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:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C3(H3A,H3B,H3C)
;
_shelx_res_file
;
TITL tw2012_a.res in Cc
    tw2012.res
    created by SHELXL-2018/3 at 15:06:36 on 23-Jun-2021
REM Old TITL TW2012 in Cc
REM SHELXT solution in Cc: R1 0.056, Rweak 0.307, Alpha 0.023
REM <I/s> 1.426 for 48 systematic absences, Orientation as input
REM Flack x = -0.009 ( 0.013 ) from 795 Parsons' quotients
REM Formula found by SHELXT: C7 N3 Br
CELL 0.71073 7.0482 11.4371 11.1712 90 94.909 90
ZERR 4 0.0003 0.0005 0.0006 0 0.005 0
LATT -7
SYMM +X,-Y,0.5+Z
SFAC C H Br N
UNIT 28 40 4 12

L.S. 10
PLAN  5
SIZE 0.2 0.17 0.15
CONF
BOND
list 4
MORE -1
BOND $H
fmap 2 53
acta
REM <olex2.extras>
REM <HklSrc "%.\\TW2012.hkl">
REM </olex2.extras>

WGHT    0.032200    1.106500
FVAR       0.49159
N1    4    0.543653    0.285254    0.326060    11.00000    0.02731    0.03088 =
         0.02331   -0.00166    0.00558    0.00124
C1    1    0.466369    0.191888    0.247085    11.00000    0.03789    0.03676 =
         0.03519   -0.00961    0.00481    0.00064
AFIX 137
H1A   2    0.401384    0.136066    0.293073    11.00000   -1.50000
H1B   2    0.568367    0.153785    0.210734    11.00000   -1.50000
H1C   2    0.378557    0.224442    0.185537    11.00000   -1.50000
AFIX   0
N2    4    0.572348    0.418450    0.461550    11.00000    0.02466    0.02389 =
         0.03270    0.00152    0.00817   -0.00037
C2    1    0.450174    0.347114    0.401979    11.00000    0.02776    0.02726 =
         0.02540    0.00460    0.00585    0.00404
N3    4    0.475764    0.415183    0.756665    11.00000    0.04880    0.03141 =
         0.03821   -0.00682    0.01113   -0.00531
C3    1    0.244620    0.340095    0.414832    11.00000    0.01851    0.04506 =
         0.03681    0.00376    0.00699    0.00490
AFIX 137
H3A   2    0.175451    0.366099    0.341920    11.00000   -1.50000
H3B   2    0.213567    0.388946    0.480256    11.00000   -1.50000
H3C   2    0.210624    0.260657    0.430713    11.00000   -1.50000
AFIX   0
C4    1    0.735287    0.317295    0.339172    11.00000    0.02291    0.03391 =
         0.04210   -0.00241    0.01593    0.00114
AFIX  43
H4    2    0.832186    0.286939    0.296923    11.00000   -1.20000
AFIX   0
C5    1    0.752974    0.399146    0.423208    11.00000    0.02287    0.03863 =
         0.03555    0.00000    0.00889   -0.00213
AFIX  43
H5    2    0.864961    0.436766    0.451423    11.00000   -1.20000
AFIX   0
C6    1    0.529604    0.505996    0.550072    11.00000    0.02238    0.02403 =
         0.02892   -0.00248    0.01072    0.00161
AFIX  23
H6A   2    0.415877    0.548441    0.520689    11.00000   -1.20000
H6B   2    0.633839    0.561503    0.559792    11.00000   -1.20000
AFIX   0
C7    1    0.500155    0.454495    0.667062    11.00000    0.01858    0.02749 =
         0.03490   -0.00980    0.00770   -0.00204

BR1   3    0.544390    0.114945    0.588430    11.00000    0.02889    0.02947 =
         0.02939   -0.00170    0.00686    0.00128
HKLF 4




REM  tw2012_a.res in Cc
REM wR2 = 0.0720, GooF = S = 1.042, Restrained GooF = 1.042 for all data
REM R1 = 0.0330 for 1782 Fo > 4sig(Fo) and 0.0365 for all 1904 data
REM 102 parameters refined using 2 restraints

END

WGHT      0.0322      1.1064

REM Highest difference peak  0.487,  deepest hole -0.370,  1-sigma level  0.069
Q1    1   0.5342  0.0367  0.5861  11.00000  0.05    0.49
Q2    1   0.6735  0.1173  0.6146  11.00000  0.05    0.45
Q3    1   0.4164  0.1193  0.5550  11.00000  0.05    0.38
Q4    1   0.5492  0.1948  0.5906  11.00000  0.05    0.37
Q5    1   0.5652  0.1180  0.5632  11.00000  0.05    0.32
;
_shelx_res_checksum              32411
_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, -y, z+1/2'
'x+1/2, y+1/2, 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 0.5437(7) 0.2853(4) 0.3261(4) 0.0270(11) Uani 1 1 d . . . . .
C1 C 0.4664(10) 0.1919(6) 0.2471(6) 0.0365(15) Uani 1 1 d . . . . .
H1A H 0.401384 0.136066 0.293073 0.055 Uiso 1 1 calc R U . . .
H1B H 0.568367 0.153785 0.210734 0.055 Uiso 1 1 calc R U . . .
H1C H 0.378557 0.224442 0.185537 0.055 Uiso 1 1 calc R U . . .
N2 N 0.5723(9) 0.4185(6) 0.4615(6) 0.0268(14) Uani 1 1 d . . . . .
C2 C 0.4502(8) 0.3471(5) 0.4020(5) 0.0266(12) Uani 1 1 d . . . . .
N3 N 0.4758(11) 0.4152(7) 0.7567(6) 0.0390(18) Uani 1 1 d . . . . .
C3 C 0.2446(9) 0.3401(6) 0.4148(6) 0.0332(14) Uani 1 1 d . . . . .
H3A H 0.175451 0.366099 0.341920 0.050 Uiso 1 1 calc R U . . .
H3B H 0.213567 0.388946 0.480256 0.050 Uiso 1 1 calc R U . . .
H3C H 0.210624 0.260657 0.430713 0.050 Uiso 1 1 calc R U . . .
C4 C 0.7353(9) 0.3173(5) 0.3392(6) 0.0322(14) Uani 1 1 d . . . . .
H4 H 0.832186 0.286939 0.296923 0.039 Uiso 1 1 calc R U . . .
C5 C 0.7530(11) 0.3991(6) 0.4232(6) 0.0320(14) Uani 1 1 d . . . . .
H5 H 0.864961 0.436766 0.451423 0.038 Uiso 1 1 calc R U . . .
C6 C 0.5296(9) 0.5060(5) 0.5501(5) 0.0246(13) Uani 1 1 d . . . . .
H6A H 0.415877 0.548441 0.520689 0.030 Uiso 1 1 calc R U . . .
H6B H 0.633839 0.561503 0.559792 0.030 Uiso 1 1 calc R U . . .
C7 C 0.5002(9) 0.4545(6) 0.6671(6) 0.0267(14) Uani 1 1 d . . . . .
Br1 Br 0.54439(6) 0.11494(4) 0.58843(5) 0.02900(17) 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
N1 0.027(3) 0.031(3) 0.023(2) -0.002(2) 0.006(2) 0.001(2)
C1 0.038(4) 0.037(4) 0.035(4) -0.010(3) 0.005(3) 0.001(3)
N2 0.025(3) 0.024(3) 0.033(4) 0.002(3) 0.008(3) 0.000(2)
C2 0.028(3) 0.027(3) 0.025(3) 0.005(2) 0.006(2) 0.004(3)
N3 0.049(5) 0.031(3) 0.038(4) -0.007(3) 0.011(3) -0.005(3)
C3 0.019(3) 0.045(4) 0.037(3) 0.004(3) 0.007(3) 0.005(3)
C4 0.023(3) 0.034(3) 0.042(4) -0.002(3) 0.016(3) 0.001(2)
C5 0.023(3) 0.039(4) 0.036(3) 0.000(3) 0.009(3) -0.002(3)
C6 0.022(3) 0.024(3) 0.029(3) -0.002(2) 0.011(3) 0.002(2)
C7 0.019(3) 0.027(4) 0.035(4) -0.010(3) 0.008(3) -0.002(3)
Br1 0.0289(3) 0.0295(3) 0.0294(3) -0.0017(4) 0.00686(19) 0.0013(4)
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 126.7(5) . . ?
C2 N1 C4 108.8(5) . . ?
C4 N1 C1 124.3(5) . . ?
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 C5 108.6(6) . . ?
C2 N2 C6 127.0(6) . . ?
C5 N2 C6 124.4(6) . . ?
N1 C2 N2 108.3(5) . . ?
N1 C2 C3 125.6(6) . . ?
N2 C2 C3 126.1(6) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 H4 126.5 . . ?
C5 C4 N1 107.0(6) . . ?
C5 C4 H4 126.5 . . ?
N2 C5 H5 126.4 . . ?
C4 C5 N2 107.3(6) . . ?
C4 C5 H5 126.4 . . ?
N2 C6 H6A 109.1 . . ?
N2 C6 H6B 109.1 . . ?
N2 C6 C7 112.5(5) . . ?
H6A C6 H6B 107.8 . . ?
C7 C6 H6A 109.1 . . ?
C7 C6 H6B 109.1 . . ?
N3 C7 C6 179.3(8) . . ?
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 1.461(8) . ?
N1 C2 1.323(7) . ?
N1 C4 1.395(8) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
N2 C2 1.324(9) . ?
N2 C5 1.395(9) . ?
N2 C6 1.457(8) . ?
C2 C3 1.470(8) . ?
N3 C7 1.124(9) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4 0.9300 . ?
C4 C5 1.324(9) . ?
C5 H5 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.464(9) . ?
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 C4 C5 N2 -0.4(7) . . . . ?
C1 N1 C2 N2 176.6(6) . . . . ?
C1 N1 C2 C3 -5.2(9) . . . . ?
C1 N1 C4 C5 -176.1(6) . . . . ?
C2 N1 C4 C5 -0.3(7) . . . . ?
C2 N2 C5 C4 1.0(8) . . . . ?
C2 N2 C6 C7 77.1(9) . . . . ?
C4 N1 C2 N2 1.0(7) . . . . ?
C4 N1 C2 C3 179.2(6) . . . . ?
C5 N2 C2 N1 -1.3(7) . . . . ?
C5 N2 C2 C3 -179.5(6) . . . . ?
C5 N2 C6 C7 -105.0(7) . . . . ?
C6 N2 C2 N1 177.0(6) . . . . ?
C6 N2 C2 C3 -1.2(11) . . . . ?
C6 N2 C5 C4 -177.2(6) . . . . ?
