# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_C11H21Cl1N2
_database_code_depnum_ccdc_archive 'CCDC 2281578'
loop_
_audit_author_name
_audit_author_address
'Deniz Bekis'
;Philipps Universitaet Marburg
Germany
;
_audit_update_record             
;
2023-07-14 deposited with the CCDC.	2023-09-21 downloaded from the CCDC.
;
_audit_creation_date             2023-04-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        
'1,3-Diisopropyl-4,5-dimethylimidazolium chloride'
_chemical_formula_moiety         'C11 H21 N2, Cl'
_chemical_formula_sum            'C11 H21 Cl N2'
_chemical_formula_weight         216.75
_chemical_melting_point          ?
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'
Cl Cl 0.3639 0.7018 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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'

_cell_length_a                   11.5065(11)
_cell_length_b                   7.5925(5)
_cell_length_c                   15.0274(14)
_cell_angle_alpha                90
_cell_angle_beta                 104.919(8)
_cell_angle_gamma                90
_cell_volume                     1268.59(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11795
_cell_measurement_temperature    100
_cell_measurement_theta_max      76.03
_cell_measurement_theta_min      3.23
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.393
_exptl_absorpt_correction_T_max  0.9110
_exptl_absorpt_correction_T_min  0.8026
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE LANA, absorption correction by scaling of reflection intensities.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(μ₂-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light red'
_exptl_crystal_density_diffrn    1.135
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.092
_exptl_crystal_size_mid          0.067
_exptl_crystal_size_min          0.039
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12584
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         75.751
_diffrn_reflns_theta_min         4.341
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_details      
; 2411 frames, detector distance = 60 mm
;
_diffrn_detector                 Pilatus300K
_diffrn_detector_type            'DECTRIS PILATUS 300K'
_diffrn_detector_area_resol_mean 5.81
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_collimation    '0.5 mm diameter'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'GeniX 3D HF Cu'
_diffrn_source_current           0.6
_diffrn_source_power             0.03
_diffrn_source_voltage           50.0
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2112
_reflns_number_total             2579
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2579
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0462
_refine_ls_restrained_S_all      1.050
_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)+(0.0786P)²+0.2876P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1223
_refine_ls_wR_factor_ref         0.1274
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(C7B)=Sof(H7BA)=Sof(H7BB)=Sof(H7BC)=1-FVAR(1)
 Sof(C7A)=Sof(H7AA)=Sof(H7AB)=Sof(H7AC)=FVAR(1)
3.a Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C5(H5A,H5B,H5C),
 C8(H8A,H8B,H8C), C7B(H7BA,H7BB,H7BC), C7A(H7AA,H7AB,H7AC)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Cl1 Cl 0.47975(4) 0.95490(6) 0.20713(3) 0.03462(17) Uani 1 1 d . . . . .
N2 N 0.71360(14) 0.5637(2) 0.38181(10) 0.0279(3) Uani 1 1 d . . . . .
N1 N 0.53421(15) 0.4563(2) 0.34628(11) 0.0337(4) Uani 1 1 d . . . . .
C1 C 0.60037(17) 0.5948(3) 0.33601(13) 0.0310(4) Uani 1 1 d . . . . .
C2 C 0.72104(18) 0.3999(3) 0.42342(12) 0.0301(4) Uani 1 1 d . . . . .
C4 C 0.60764(19) 0.3330(3) 0.40187(12) 0.0329(4) Uani 1 1 d . . . . .
C9 C 0.81518(17) 0.6904(3) 0.39381(13) 0.0311(4) Uani 1 1 d . . . . .
C3 C 0.83743(19) 0.3234(3) 0.47711(13) 0.0353(4) Uani 1 1 d . . . . .
H3A H 0.895268 0.324136 0.439303 0.053 Uiso 1 1 calc R U . . .
H3B H 0.824461 0.202016 0.494551 0.053 Uiso 1 1 calc R U . . .
H3C H 0.869024 0.393798 0.532746 0.053 Uiso 1 1 calc R U . . .
C10 C 0.8319(2) 0.7849(3) 0.48539(15) 0.0389(5) Uani 1 1 d . . . . .
H10A H 0.757727 0.847559 0.486240 0.058 Uiso 1 1 calc R U . . .
H10B H 0.898162 0.869452 0.493379 0.058 Uiso 1 1 calc R U . . .
H10C H 0.850602 0.698719 0.535595 0.058 Uiso 1 1 calc R U . . .
C6 C 0.4022(2) 0.4414(4) 0.30654(15) 0.0428(5) Uani 1 1 d . . . . .
C11 C 0.7939(2) 0.8160(4) 0.31270(16) 0.0446(6) Uani 1 1 d . . . . .
H11A H 0.784563 0.748674 0.255656 0.067 Uiso 1 1 calc R U . . .
H11B H 0.862720 0.895974 0.320645 0.067 Uiso 1 1 calc R U . . .
H11C H 0.720786 0.884613 0.309393 0.067 Uiso 1 1 calc R U . . .
C5 C 0.5604(2) 0.1644(3) 0.42969(15) 0.0430(5) Uani 1 1 d . . . . .
H5A H 0.495597 0.189641 0.459198 0.065 Uiso 1 1 calc R U . . .
H5B H 0.625413 0.101600 0.473088 0.065 Uiso 1 1 calc R U . . .
H5C H 0.529282 0.091107 0.375056 0.065 Uiso 1 1 calc R U . . .
C8 C 0.3707(2) 0.4676(5) 0.20513(17) 0.0570(7) Uani 1 1 d . . . . .
H8A H 0.395406 0.585855 0.191271 0.085 Uiso 1 1 calc R U . . .
H8B H 0.283661 0.454793 0.180215 0.085 Uiso 1 1 calc R U . . .
H8C H 0.412430 0.379470 0.177044 0.085 Uiso 1 1 calc R U . . .
C7B C 0.3452(5) 0.505(2) 0.3711(6) 0.059(3) Uani 0.457(16) 1 d . . P A 2
H7BA H 0.382002 0.452842 0.431340 0.089 Uiso 0.457(16) 1 calc R U P A 2
H7BB H 0.259647 0.474473 0.352210 0.089 Uiso 0.457(16) 1 calc R U P A 2
H7BC H 0.353775 0.633688 0.375216 0.089 Uiso 0.457(16) 1 calc R U P A 2
H6 H 0.386(3) 0.327(4) 0.316(2) 0.064(9) Uiso 1 1 d . . . . .
H1 H 0.571(2) 0.693(3) 0.3017(15) 0.030(6) Uiso 1 1 d . . . . .
H9 H 0.8811(19) 0.618(3) 0.3917(14) 0.024(5) Uiso 1 1 d . . . . .
C7A C 0.3357(4) 0.6151(12) 0.3376(5) 0.047(2) Uani 0.543(16) 1 d . . P A 1
H7AA H 0.357338 0.623841 0.404946 0.071 Uiso 0.543(16) 1 calc R U P A 1
H7AB H 0.248289 0.602802 0.314761 0.071 Uiso 0.543(16) 1 calc R U P A 1
H7AC H 0.362026 0.721634 0.311596 0.071 Uiso 0.543(16) 1 calc R U P A 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
N2 C1 1.329(3) . ?
N2 C2 1.385(2) . ?
N2 C9 1.488(2) . ?
N1 C1 1.330(3) . ?
N1 C4 1.387(3) . ?
N1 C6 1.487(3) . ?
C1 H1 0.92(2) . ?
C2 C4 1.359(3) . ?
C2 C3 1.492(3) . ?
C4 C5 1.492(3) . ?
C9 C10 1.520(3) . ?
C9 C11 1.517(3) . ?
C9 H9 0.94(2) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C6 C8 1.486(3) . ?
C6 C7B 1.391(6) . ?
C6 H6 0.91(3) . ?
C6 C7A 1.651(7) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C7B H7BA 0.9800 . ?
C7B H7BB 0.9800 . ?
C7B H7BC 0.9800 . ?
C7A H7AA 0.9800 . ?
C7A H7AB 0.9800 . ?
C7A H7AC 0.9800 . ?

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
C1 N2 C2 109.38(17) . . ?
C1 N2 C9 125.64(17) . . ?
C2 N2 C9 124.78(16) . . ?
C1 N1 C4 108.98(17) . . ?
C1 N1 C6 124.72(19) . . ?
C4 N1 C6 126.26(18) . . ?
N2 C1 N1 108.28(18) . . ?
N2 C1 H1 126.8(15) . . ?
N1 C1 H1 124.9(15) . . ?
N2 C2 C3 122.43(18) . . ?
C4 C2 N2 106.50(17) . . ?
C4 C2 C3 131.03(19) . . ?
N1 C4 C5 122.6(2) . . ?
C2 C4 N1 106.84(18) . . ?
C2 C4 C5 130.6(2) . . ?
N2 C9 C10 109.11(16) . . ?
N2 C9 C11 110.48(16) . . ?
N2 C9 H9 103.5(13) . . ?
C10 C9 H9 113.0(13) . . ?
C11 C9 C10 112.79(19) . . ?
C11 C9 H9 107.6(13) . . ?
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 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C6 H6 104(2) . . ?
N1 C6 C7A 109.0(2) . . ?
C8 C6 N1 110.81(19) . . ?
C8 C6 H6 107(2) . . ?
C8 C6 C7A 100.1(4) . . ?
C7B C6 N1 108.0(3) . . ?
C7B C6 C8 129.4(5) . . ?
C7B C6 H6 94(2) . . ?
C7A C6 H6 126(2) . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C7B H7BA 109.5 . . ?
C6 C7B H7BB 109.5 . . ?
C6 C7B H7BC 109.5 . . ?
H7BA C7B H7BB 109.5 . . ?
H7BA C7B H7BC 109.5 . . ?
H7BB C7B H7BC 109.5 . . ?
C6 C7A H7AA 109.5 . . ?
C6 C7A H7AB 109.5 . . ?
C6 C7A H7AC 109.5 . . ?
H7AA C7A H7AB 109.5 . . ?
H7AA C7A H7AC 109.5 . . ?
H7AB C7A H7AC 109.5 . . ?

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
N2 C2 C4 N1 1.1(2) . . . . ?
N2 C2 C4 C5 -177.86(19) . . . . ?
C1 N2 C2 C4 -0.5(2) . . . . ?
C1 N2 C2 C3 177.56(17) . . . . ?
C1 N2 C9 C10 95.5(2) . . . . ?
C1 N2 C9 C11 -29.1(3) . . . . ?
C1 N1 C4 C2 -1.2(2) . . . . ?
C1 N1 C4 C5 177.80(18) . . . . ?
C1 N1 C6 C8 55.8(3) . . . . ?
C1 N1 C6 C7B -91.1(8) . . . . ?
C1 N1 C6 C7A -53.4(4) . . . . ?
C2 N2 C1 N1 -0.2(2) . . . . ?
C2 N2 C9 C10 -78.8(2) . . . . ?
C2 N2 C9 C11 156.62(18) . . . . ?
C4 N1 C1 N2 0.9(2) . . . . ?
C4 N1 C6 C8 -126.4(2) . . . . ?
C4 N1 C6 C7B 86.7(8) . . . . ?
C4 N1 C6 C7A 124.4(4) . . . . ?
C9 N2 C1 N1 -175.27(16) . . . . ?
C9 N2 C2 C4 174.55(16) . . . . ?
C9 N2 C2 C3 -7.3(3) . . . . ?
C3 C2 C4 N1 -176.82(19) . . . . ?
C3 C2 C4 C5 4.3(4) . . . . ?
C6 N1 C1 N2 179.00(18) . . . . ?
C6 N1 C4 C2 -179.30(18) . . . . ?
C6 N1 C4 C5 -0.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
