#------------------------------------------------------------------------------
#$Date: 2022-03-03 02:49:29 +0100 (jue 03 de mar de 2022) $
#$Revision: 273215 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/45/7244554.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_7244554
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         '0.5(C12 H16 N6), Cl'
_chemical_formula_sum            'C6 H8 Cl N3'
_chemical_formula_weight         157.60
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.9547(5)
_cell_length_b                   6.2734(2)
_cell_length_c                   7.8292(3)
_cell_measurement_reflns_used    2661
_cell_measurement_temperature    173.00(14)
_cell_measurement_theta_max      28.0540
_cell_measurement_theta_min      2.9350
_cell_volume                     734.51(4)
_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    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(14)
_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 0.934
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -37.00  51.00   1.00    3.33    --  -13.18  77.00  60.00   88
  2  ω    -30.00  56.00   1.00    3.33    --  -13.18  37.00-120.00   86
  3  ω     13.00  82.00   1.00    3.33    --   14.27  57.00-150.00   69
  4  ω    -25.00  26.00   1.00    3.33    --  -13.18 -99.00   0.00   51
  5  ω     -2.00  67.00   1.00    3.33    --   14.27-123.00  15.00   69
  6  ω    -80.00   6.00   1.00    3.33    --  -13.18 -77.00 -60.00   86
  7  ω    -82.00   4.00   1.00    3.33    --  -13.18 -37.00  60.00   86
  8  ω    -67.00   3.00   1.00    3.33    --  -13.18 125.00 142.09   70
;
_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      0.0263948000
_diffrn_orient_matrix_UB_12      -0.0939026000
_diffrn_orient_matrix_UB_13      0.0000890000
_diffrn_orient_matrix_UB_21      0.0391871000
_diffrn_orient_matrix_UB_22      0.0625065000
_diffrn_orient_matrix_UB_23      0.0100748000
_diffrn_orient_matrix_UB_31      -0.0043972000
_diffrn_orient_matrix_UB_32      -0.0068795000
_diffrn_orient_matrix_UB_33      0.0900347000
_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  0.0374
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9241
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.280
_diffrn_reflns_theta_min         2.724
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.442
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92882
_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    1.425
_exptl_crystal_description       plate
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.384
_exptl_crystal_size_mid          0.183
_exptl_crystal_size_min          0.026
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     62
_refine_ls_number_reflns         926
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0310
_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)+(0.0331P)²+0.2641P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.0741
_reflns_Friedel_coverage         0.000
_reflns_number_gt                790
_reflns_number_total             926
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cp05169e5.cif
_cod_data_source_block           '[NC2C1im]Cl'
_cod_database_code               7244554
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C6 H8 Cl N3'
_chemical_oxdiff_usercomment     SK56_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.
;
_reflns_odcompleteness_completeness 99.87
_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. Others
 Fixed Sof: H1A(0.5) H1B(0.5) H1C(0.5) H6A(0.5) H6B(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5)
3.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_file
;
TITL CF solution in Pnma
    tw2102.res
    created by SHELXL-2018/3 at 15:25:06 on 23-Jun-2021
CELL 0.71073 14.95469 6.2734 7.82916 90 90 90
ZERR 4 0.0005 0.00024 0.00025 0 0 0
LATT 1
SYMM 0.5-X,-Y,0.5+Z
SYMM 0.5+X,0.5-Y,0.5-Z
SYMM -X,0.5+Y,-Z
SFAC C H Cl N
UNIT 24 32 4 12

L.S. 10
PLAN  5
CONF
BOND
MORE -1
BOND $H
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\TW2102.hkl">
REM </olex2.extras>

WGHT    0.033100    0.264100
FVAR       4.96629
N1    4    0.147259    0.750000    0.347455    10.50000    0.01807    0.01665 =
         0.01875    0.00000   -0.00311    0.00000
C1    1    0.049178    0.750000    0.355346    10.50000    0.01786    0.02902 =
         0.03129    0.00000   -0.00614    0.00000
PART -1
AFIX 137
H1A   2    0.026876    0.615527    0.315219    10.50000   -1.50000
H1B   2    0.026204    0.862505    0.284756    10.50000   -1.50000
H1C   2    0.030316    0.771969    0.471222    10.50000   -1.50000
AFIX   0
PART 0
N2    4    0.285349    0.750000    0.425691    10.50000    0.01736    0.01965 =
         0.01168    0.00000   -0.00169    0.00000
C2    1    0.200998    0.750000    0.482478    10.50000    0.01851    0.01648 =
         0.01410    0.00000    0.00036    0.00000
AFIX  43
H2    2    0.183158    0.750000    0.596272    10.50000   -1.20000
AFIX   0
N3    4    0.335262    0.750000    0.852270    10.50000    0.03286    0.02641 =
         0.01783    0.00000    0.00045    0.00000
C4    1    0.198177    0.750000    0.201107    10.50000    0.02969    0.01956 =
         0.01354    0.00000   -0.00340    0.00000
AFIX  43
H4    2    0.176955    0.750000    0.089452    10.50000   -1.20000
AFIX   0
C5    1    0.284621    0.750000    0.249973    10.50000    0.02517    0.02175 =
         0.01187    0.00000    0.00232    0.00000
AFIX  43
H5    2    0.334297    0.750000    0.178512    10.50000   -1.20000
AFIX   0
C6    1    0.368355    0.750000    0.525845    10.50000    0.01610    0.02414 =
         0.01515    0.00000   -0.00189    0.00000
AFIX  23
H6A   2    0.403355    0.624910    0.496970    10.50000   -1.20000
H6B   2    0.403355    0.875090    0.496971    10.50000   -1.20000
AFIX   0
C7    1    0.349660    0.750000    0.709531    10.50000    0.01765    0.01717 =
         0.02130    0.00000   -0.00419    0.00000

CL1   3    0.570815    0.750000    0.667678    10.50000    0.01804    0.02965 =
         0.01704    0.00000   -0.00040    0.00000
HKLF 4




REM  CF solution in Pnma
REM wR2 = 0.0741, GooF = S = 1.081, Restrained GooF = 1.081 for all data
REM R1 = 0.0310 for 790 Fo > 4sig(Fo) and 0.0386 for all 926 data
REM 62 parameters refined using 0 restraints

END

WGHT      0.0331      0.2641

REM Highest difference peak  0.191,  deepest hole -0.333,  1-sigma level  0.082
Q1    1   0.3547  1.0349  0.4160  11.00000  0.05    0.19
Q2    1   0.3978  0.9626  0.3490  11.00000  0.05    0.18
Q3    1   0.2859  0.7758  0.3388  11.00000  0.05    0.17
Q4    1   0.1360  0.9649  0.6628  11.00000  0.05    0.17
Q5    1   0.0105  1.0120  0.2177  11.00000  0.05    0.17
;
_shelx_res_checksum              66130
_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 1.084
_oxdiff_exptl_absorpt_empirical_full_min 0.960
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'
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 0.14726(11) 0.750000 0.3475(2) 0.0178(3) Uani 1 2 d S T P . .
C1 C 0.04918(13) 0.750000 0.3553(3) 0.0261(5) Uani 1 2 d S T P . .
H1A H 0.026876 0.615527 0.315219 0.039 Uiso 0.5 1 calc R U P A -1
H1B H 0.026204 0.862505 0.284756 0.039 Uiso 0.5 1 calc R U P A -1
H1C H 0.030316 0.771969 0.471222 0.039 Uiso 0.5 1 calc R U P A -1
N2 N 0.28535(10) 0.750000 0.42569(18) 0.0162(3) Uani 1 2 d S T P . .
C2 C 0.20100(12) 0.750000 0.4825(2) 0.0164(4) Uani 1 2 d S T P . .
H2 H 0.183158 0.750000 0.596272 0.020 Uiso 1 2 calc R U P . .
N3 N 0.33526(12) 0.750000 0.8523(2) 0.0257(4) Uani 1 2 d S T P . .
C4 C 0.19818(13) 0.750000 0.2011(2) 0.0209(4) Uani 1 2 d S T P . .
H4 H 0.176955 0.750000 0.089452 0.025 Uiso 1 2 calc R U P . .
C5 C 0.28462(13) 0.750000 0.2500(2) 0.0196(4) Uani 1 2 d S T P . .
H5 H 0.334297 0.750000 0.178512 0.024 Uiso 1 2 calc R U P . .
C6 C 0.36835(12) 0.750000 0.5258(2) 0.0185(4) Uani 1 2 d S T P . .
H6A H 0.403355 0.624910 0.496970 0.022 Uiso 0.5 1 calc R U P . .
H6B H 0.403355 0.875090 0.496971 0.022 Uiso 0.5 1 calc R U P . .
C7 C 0.34966(13) 0.750000 0.7095(3) 0.0187(4) Uani 1 2 d S T P . .
Cl1 Cl 0.57081(3) 0.750000 0.66768(6) 0.02157(16) Uani 1 2 d S T P . .
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 0.0181(8) 0.0167(8) 0.0187(8) 0.000 -0.0031(6) 0.000
C1 0.0179(10) 0.0290(11) 0.0313(11) 0.000 -0.0061(8) 0.000
N2 0.0174(8) 0.0196(8) 0.0117(7) 0.000 -0.0017(6) 0.000
C2 0.0185(9) 0.0165(9) 0.0141(9) 0.000 0.0004(7) 0.000
N3 0.0329(10) 0.0264(9) 0.0178(9) 0.000 0.0004(7) 0.000
C4 0.0297(11) 0.0196(10) 0.0135(9) 0.000 -0.0034(8) 0.000
C5 0.0252(11) 0.0217(10) 0.0119(9) 0.000 0.0023(7) 0.000
C6 0.0161(9) 0.0241(10) 0.0151(9) 0.000 -0.0019(7) 0.000
C7 0.0177(10) 0.0172(9) 0.0213(10) 0.000 -0.0042(7) 0.000
Cl1 0.0180(3) 0.0296(3) 0.0170(3) 0.000 -0.00040(18) 0.000
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'
Cl Cl 0.1484 0.1585 '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 124.83(16) . . ?
C2 N1 C4 109.15(16) . . ?
C4 N1 C1 126.02(16) . . ?
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 108.96(16) . . ?
C2 N2 C6 128.31(15) . . ?
C5 N2 C6 122.73(15) . . ?
N1 C2 N2 107.83(16) . . ?
N1 C2 H2 126.1 . . ?
N2 C2 H2 126.1 . . ?
N1 C4 H4 126.4 . . ?
C5 C4 N1 107.12(16) . . ?
C5 C4 H4 126.4 . . ?
N2 C5 H5 126.5 . . ?
C4 C5 N2 106.94(17) . . ?
C4 C5 H5 126.5 . . ?
N2 C6 H6A 109.4 . . ?
N2 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C7 C6 N2 111.28(15) . . ?
C7 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
N3 C7 C6 179.9(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 1.468(2) . ?
N1 C2 1.328(2) . ?
N1 C4 1.376(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
N2 C2 1.337(2) . ?
N2 C5 1.376(2) . ?
N2 C6 1.468(2) . ?
C2 H2 0.9300 . ?
N3 C7 1.138(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.348(3) . ?
C5 H5 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.465(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 0.000(0) . . . . ?
C1 N1 C2 N2 180.000(0) . . . . ?
C1 N1 C4 C5 180.000(0) . . . . ?
C2 N1 C4 C5 0.000(0) . . . . ?
C2 N2 C5 C4 0.000(0) . . . . ?
C2 N2 C6 C7 0.000(0) . . . . ?
C4 N1 C2 N2 0.000(0) . . . . ?
C5 N2 C2 N1 0.000(0) . . . . ?
C5 N2 C6 C7 180.000(0) . . . . ?
C6 N2 C2 N1 180.000(0) . . . . ?
C6 N2 C5 C4 180.000(0) . . . . ?
