#------------------------------------------------------------------------------
#$Date: 2022-03-03 03:49:29 +0200 (Thu, 03 Mar 2022) $
#$Revision: 273215 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/45/7244550.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_7244550
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, Cl'
_chemical_formula_sum            'C7 H10 Cl N3'
_chemical_formula_weight         171.63
_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                 90.240(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3329(3)
_cell_length_b                   9.3234(4)
_cell_length_c                   12.2867(4)
_cell_measurement_reflns_used    1717
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      72.5560
_cell_measurement_theta_min      5.9420
_cell_volume                     840.00(6)
_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 10.4115
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      4.00  93.00   1.00    1.00    --   42.36-125.00-180.00   89
  2  ω     36.00 102.00   1.00    1.00    --  105.13 -77.00-120.00   66
  3  ω     26.00  60.00   1.00    1.00    --   42.36-125.00  60.00   34
  4  ω     74.00 138.00   1.00    1.00    --  105.13 -77.00  60.00   64
  5  ω     92.00 176.00   1.00    1.00    --  105.13  61.00  60.00   84
  6  ω     19.00  45.00   1.00    1.00    --   42.23  57.00 -30.00   26
  7  ω     73.00  98.00   1.00    1.00    --   42.23-125.00-180.00   25
  8  ω     54.00 109.00   1.00    1.00    --   42.23  57.00 -30.00   55
  9  ω     71.00  97.00   1.00    1.00    --  105.13 -95.00-180.00   26
 10  ω     31.00 104.00   1.00    1.00    --  105.13 -30.00 -60.00   73
 11  ω     35.00  74.00   1.00    1.00    --  105.13 -45.00 -90.00   39
 12  ω     42.00  87.00   1.00    1.00    --  105.13 -30.00  90.00   45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1852036000
_diffrn_orient_matrix_UB_12      0.0131060000
_diffrn_orient_matrix_UB_13      -0.0579043000
_diffrn_orient_matrix_UB_21      -0.0235513000
_diffrn_orient_matrix_UB_22      0.1525066000
_diffrn_orient_matrix_UB_23      0.0461467000
_diffrn_orient_matrix_UB_31      0.0963640000
_diffrn_orient_matrix_UB_32      0.0621793000
_diffrn_orient_matrix_UB_33      -0.1011768000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3152
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.299
_diffrn_reflns_theta_min         5.958
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.521
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88200
_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    1.357
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1629
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0353
_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)+(0.0486P)²+0.2804P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.0953
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1374
_reflns_number_total             1629
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cp05169e5.cif
_cod_data_source_block           '[NC2C1C1im]Cl'
_cod_database_code               7244550
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C7 H10 Cl N3'
_chemical_oxdiff_usercomment     SK62_ISOP
_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   0.554
_shelx_estimated_absorpt_t_min   0.461
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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)
;
_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 1.165
_oxdiff_exptl_absorpt_empirical_full_min 0.823
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 0.1985(2) 0.40809(18) 0.45967(12) 0.0241(4) Uani 1 1 d . . . . .
C1 C 0.2749(3) 0.3100(2) 0.54100(16) 0.0322(5) Uani 1 1 d . . . . .
H1A H 0.180954 0.246786 0.566536 0.048 Uiso 1 1 calc R U . . .
H1B H 0.322916 0.364176 0.601042 0.048 Uiso 1 1 calc R U . . .
H1C H 0.370889 0.254564 0.508742 0.048 Uiso 1 1 calc R U . . .
N2 N 0.0703(2) 0.49168(18) 0.31548(12) 0.0223(3) Uani 1 1 d . . . . .
C2 C 0.1005(2) 0.3714(2) 0.37281(15) 0.0232(4) Uani 1 1 d . . . . .
N3 N 0.1859(3) 0.4137(2) 0.05208(14) 0.0360(4) Uani 1 1 d . . . . .
C3 C 0.0304(3) 0.2270(2) 0.34559(17) 0.0306(4) Uani 1 1 d . . . . .
H3A H 0.093086 0.190921 0.282876 0.046 Uiso 1 1 calc R U . . .
H3B H -0.097874 0.232790 0.330165 0.046 Uiso 1 1 calc R U . . .
H3C H 0.050338 0.163669 0.406062 0.046 Uiso 1 1 calc R U . . .
C4 C 0.2329(3) 0.5541(2) 0.45740(15) 0.0257(4) Uani 1 1 d . . . . .
H4 H 0.298974 0.606021 0.508765 0.031 Uiso 1 1 calc R U . . .
C5 C 0.1531(2) 0.6069(2) 0.36728(15) 0.0240(4) Uani 1 1 d . . . . .
H5 H 0.153363 0.701913 0.344192 0.029 Uiso 1 1 calc R U . . .
C6 C -0.0234(3) 0.5006(2) 0.21021(14) 0.0252(4) Uani 1 1 d . . . . .
H6A H -0.059707 0.599045 0.196575 0.030 Uiso 1 1 calc R U . . .
H6B H -0.132718 0.442057 0.211926 0.030 Uiso 1 1 calc R U . . .
C7 C 0.0961(3) 0.4510(2) 0.12185(15) 0.0255(4) Uani 1 1 d . . . . .
Cl1 Cl 0.55446(6) 0.37168(5) 0.28871(4) 0.02751(16) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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 126.26(18) . . ?
C2 N1 C4 109.54(16) . . ?
C4 N1 C1 123.97(17) . . ?
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 109.58(15) . . ?
C2 N2 C6 125.94(16) . . ?
C5 N2 C6 124.33(16) . . ?
N1 C2 N2 107.12(16) . . ?
N1 C2 C3 127.02(17) . . ?
N2 C2 C3 125.81(17) . . ?
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 126.3 . . ?
C5 C4 N1 107.35(17) . . ?
C5 C4 H4 126.3 . . ?
N2 C5 H5 126.8 . . ?
C4 C5 N2 106.40(17) . . ?
C4 C5 H5 126.8 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
N2 C6 C7 110.77(15) . . ?
H6A C6 H6B 108.1 . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
N3 C7 C6 178.6(2) . . ?
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 1.465(2) . ?
N1 C2 1.329(2) . ?
N1 C4 1.385(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
N2 C2 1.342(2) . ?
N2 C5 1.387(2) . ?
N2 C6 1.465(2) . ?
C2 C3 1.479(3) . ?
N3 C7 1.138(3) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4 0.9300 . ?
C4 C5 1.344(3) . ?
C5 H5 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.473(3) . ?
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 0.1(2) . . . . ?
C1 N1 C2 N2 -175.12(16) . . . . ?
C1 N1 C2 C3 7.2(3) . . . . ?
C1 N1 C4 C5 175.02(16) . . . . ?
C2 N1 C4 C5 0.3(2) . . . . ?
C2 N2 C5 C4 -0.4(2) . . . . ?
C2 N2 C6 C7 -76.2(2) . . . . ?
C4 N1 C2 N2 -0.5(2) . . . . ?
C4 N1 C2 C3 -178.18(18) . . . . ?
C5 N2 C2 N1 0.6(2) . . . . ?
C5 N2 C2 C3 178.27(18) . . . . ?
C5 N2 C6 C7 99.0(2) . . . . ?
C6 N2 C2 N1 176.34(16) . . . . ?
C6 N2 C2 C3 -6.0(3) . . . . ?
C6 N2 C5 C4 -176.26(16) . . . . ?
