#------------------------------------------------------------------------------
#$Date: 2022-03-29 11:25:19 +0300 (Tue, 29 Mar 2022) $
#$Revision: 274076 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/49/8104922.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_8104922
loop_
_publ_author_name
'Hosten, Eric C.'
'Betz, Richard'
_publ_section_title
;
 The crystal structure of 2-iso-propylimidazole, C6H10N2
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              201
_journal_page_last               203
_journal_paper_doi               10.1515/ncrs-2020-0508
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C6 H10 N2'
_chemical_formula_sum            'C6 H10 N2'
_chemical_formula_weight         110.16
_chemical_name_common            2-iso-propylimidazole
_chemical_name_systematic        2-iso-propylimidazole
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     SHELXS
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                96.667(3)
_cell_angle_beta                 95.650(3)
_cell_angle_gamma                100.999(3)
_cell_formula_units_Z            4
_cell_length_a                   7.4423(5)
_cell_length_b                   7.9420(5)
_cell_length_c                   11.6711(8)
_cell_measurement_reflns_used    7265
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.36
_cell_measurement_theta_min      2.64
_cell_volume                     667.42(8)
_computing_cell_refinement       'SAINT [1]'
_computing_data_collection       'APEX2 [1]'
_computing_data_reduction        'SAINT [1]'
_computing_molecular_graphics    'ORTEP3 [3], Mercury [4]'
_computing_publication_material  'SHELXL-97 [2], PLATON [5]'
_computing_structure_refinement  'SHELXL-97 [2]'
_computing_structure_solution    'SHELXS-97 [2]'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_sigmaI/netI    0.0198
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11379
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.434
_diffrn_reflns_theta_min         2.638
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6444
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;                                                              
SADABS [6]                                         
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.096
_exptl_crystal_description       platelet
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.570
_exptl_crystal_size_mid          0.358
_exptl_crystal_size_min          0.356
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3298
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0620
_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)+(0.0741P)²+0.3012P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1578
_refine_ls_wR_factor_ref         0.1681
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2837
_reflns_number_total             3298
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2020-0508_suppl.cif
_cod_data_source_block           g
_cod_database_code               8104922
_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_min   0.955
_shelx_estimated_absorpt_t_max   0.976
_iucr_geom_bonds_special_details
;                                                              
Cg(1) is the centroid of carbon atoms N21--C21--N22--C23--C22.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
N11 N 0.39683(17) 0.29685(16) 0.18912(11) 0.0355(3) Uani 1 1 d . . . . .
N12 N 0.19887(17) 0.05819(16) 0.20147(11) 0.0368(3) Uani 1 1 d . . . . .
N21 N 0.83962(18) 0.86244(16) 0.21919(11) 0.0353(3) Uani 1 1 d . . . . .
N22 N 0.62231(17) 0.63402(16) 0.22126(12) 0.0392(3) Uani 1 1 d . . . . .
C11 C 0.30405(18) 0.20039(17) 0.26070(12) 0.0308(3) Uani 1 1 d . . . . .
C12 C 0.3488(2) 0.2120(2) 0.07865(13) 0.0415(4) Uani 1 1 d . . . . .
H12 H 0.391540 0.248536 0.009712 0.050 Uiso 1 1 calc R U . . .
C13 C 0.2282(2) 0.0657(2) 0.08739(13) 0.0418(4) Uani 1 1 d . . . . .
H13 H 0.171407 -0.020035 0.023909 0.050 Uiso 1 1 calc R U . . .
C14 C 0.3284(2) 0.2513(2) 0.38974(13) 0.0408(4) Uani 1 1 d . . . . .
H14 H 0.310794 0.373339 0.404627 0.049 Uiso 1 1 calc R U . . .
C15 C 0.5220(3) 0.2491(4) 0.44266(17) 0.0725(7) Uani 1 1 d . . . . .
H15A H 0.544801 0.131423 0.428343 0.109 Uiso 1 1 calc R U . . .
H15B H 0.535169 0.286600 0.526612 0.109 Uiso 1 1 calc R U . . .
H15C H 0.611397 0.327979 0.407257 0.109 Uiso 1 1 calc R U . . .
C16 C 0.1862(4) 0.1417(4) 0.44722(18) 0.0882(9) Uani 1 1 d . . . . .
H16A H 0.062796 0.153208 0.415765 0.132 Uiso 1 1 calc R U . . .
H16B H 0.206053 0.180048 0.531203 0.132 Uiso 1 1 calc R U . . .
H16C H 0.197009 0.020267 0.432223 0.132 Uiso 1 1 calc R U . . .
C21 C 0.8002(2) 0.68992(18) 0.21647(14) 0.0361(3) Uani 1 1 d . . . . .
C22 C 0.6794(2) 0.92056(19) 0.22464(14) 0.0405(4) Uani 1 1 d . . . . .
H22 H 0.664175 1.036926 0.226901 0.049 Uiso 1 1 calc R U . . .
C23 C 0.5471(2) 0.7795(2) 0.22616(14) 0.0397(4) Uani 1 1 d . . . . .
H23 H 0.420380 0.780409 0.230055 0.048 Uiso 1 1 calc R U . . .
H11 H 0.470(3) 0.403(3) 0.206(2) 0.065(6) Uiso 1 1 d . . . . .
H21 H 0.949(3) 0.926(3) 0.2195(19) 0.063(6) Uiso 1 1 d . . . . .
C24 C 0.9472(3) 0.5847(3) 0.2081(2) 0.0670(5) Uani 0.508(6) 1 d D . P A 1
H24 H 1.026224 0.634220 0.150740 0.080 Uiso 0.508(6) 1 calc R U P A 1
C25 C 1.0715(7) 0.6162(7) 0.3232(5) 0.0670(5) Uani 0.508(6) 1 d D . P A 1
H25A H 1.163342 0.542902 0.318938 0.101 Uiso 0.508(6) 1 calc R U P A 1
H25B H 0.996893 0.587681 0.385656 0.101 Uiso 0.508(6) 1 calc R U P A 1
H25C H 1.134262 0.738181 0.339205 0.101 Uiso 0.508(6) 1 calc R U P A 1
C26 C 0.8827(7) 0.4014(6) 0.1635(6) 0.0670(5) Uani 0.508(6) 1 d D . P A 1
H26A H 0.808379 0.389416 0.087763 0.101 Uiso 0.508(6) 1 calc R U P A 1
H26B H 0.807439 0.344778 0.217963 0.101 Uiso 0.508(6) 1 calc R U P A 1
H26C H 0.989009 0.346816 0.154762 0.101 Uiso 0.508(6) 1 calc R U P A 1
C27 C 0.9472(3) 0.5847(3) 0.2081(2) 0.0670(5) Uani 0.354(6) 1 d D . P A 2
H27 H 1.053028 0.658193 0.179014 0.080 Uiso 0.354(6) 1 calc R U P A 2
C28 C 1.0171(11) 0.5498(11) 0.3250(6) 0.0670(5) Uani 0.354(6) 1 d D . P A 2
H28A H 0.922419 0.466245 0.352982 0.101 Uiso 0.354(6) 1 calc R U P A 2
H28B H 1.046207 0.657932 0.379133 0.101 Uiso 0.354(6) 1 calc R U P A 2
H28C H 1.128582 0.502102 0.319805 0.101 Uiso 0.354(6) 1 calc R U P A 2
C29 C 0.8727(10) 0.4263(9) 0.1121(9) 0.0670(5) Uani 0.354(6) 1 d D . P A 2
H29A H 0.767657 0.350559 0.136789 0.101 Uiso 0.354(6) 1 calc R U P A 2
H29B H 0.970497 0.361667 0.099678 0.101 Uiso 0.354(6) 1 calc R U P A 2
H29C H 0.833001 0.466974 0.039515 0.101 Uiso 0.354(6) 1 calc R U P A 2
C30 C 0.9472(3) 0.5847(3) 0.2081(2) 0.0670(5) Uani 0.137(3) 1 d D . P A 3
H30 H 1.066124 0.668241 0.236423 0.080 Uiso 0.137(3) 1 calc R U P A 3
C31 C 0.929(2) 0.4513(19) 0.2963(14) 0.0670(5) Uani 0.137(3) 1 d D . P A 3
H31A H 0.815256 0.363752 0.272622 0.101 Uiso 0.137(3) 1 calc R U P A 3
H31B H 0.924769 0.511264 0.374019 0.101 Uiso 0.137(3) 1 calc R U P A 3
H31C H 1.035205 0.394973 0.297881 0.101 Uiso 0.137(3) 1 calc R U P A 3
C32 C 0.964(2) 0.518(2) 0.0923(12) 0.0670(5) Uani 0.137(3) 1 d D . P A 3
H32A H 0.842954 0.455436 0.053519 0.101 Uiso 0.137(3) 1 calc R U P A 3
H32B H 1.050078 0.438787 0.093398 0.101 Uiso 0.137(3) 1 calc R U P A 3
H32C H 1.010578 0.613751 0.050186 0.101 Uiso 0.137(3) 1 calc R U P A 3
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'
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
C11 N11 C12 107.78(12) . .
C11 N11 H11 128.6(15) . .
C12 N11 H11 123.4(15) . .
C11 N12 C13 105.35(12) . .
C21 N21 C22 107.87(12) . .
C21 N21 H21 125.8(15) . .
C22 N21 H21 126.3(15) . .
C21 N22 C23 105.37(12) . .
N12 C11 N11 110.74(12) . .
N12 C11 C14 126.74(13) . .
N11 C11 C14 122.48(12) . .
C13 C12 N11 105.85(13) . .
C13 C12 H12 127.1 . .
N11 C12 H12 127.1 . .
C12 C13 N12 110.28(13) . .
C12 C13 H13 124.9 . .
N12 C13 H13 124.9 . .
C11 C14 C16 112.07(15) . .
C11 C14 C15 111.26(14) . .
C16 C14 C15 111.32(18) . .
C11 C14 H14 107.3 . .
C16 C14 H14 107.3 . .
C15 C14 H14 107.3 . .
C14 C15 H15A 109.5 . .
C14 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C14 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C14 C16 H16A 109.5 . .
C14 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C14 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
N22 C21 N21 110.74(13) . .
N22 C21 C30 127.88(15) . .
N21 C21 C30 121.38(15) . .
N22 C21 C24 127.88(15) . .
N21 C21 C24 121.38(15) . .
N22 C21 C27 127.88(15) . .
N21 C21 C27 121.38(15) . .
C23 C22 N21 106.00(13) . .
C23 C22 H22 127.0 . .
N21 C22 H22 127.0 . .
C22 C23 N22 110.02(13) . .
C22 C23 H23 125.0 . .
N22 C23 H23 125.0 . .
C26 C24 C21 115.8(2) . .
C26 C24 C25 113.2(3) . .
C21 C24 C25 109.6(2) . .
C26 C24 H24 105.8 . .
C21 C24 H24 105.8 . .
C25 C24 H24 105.8 . .
C24 C25 H25A 109.5 . .
C24 C25 H25B 109.5 . .
H25A C25 H25B 109.5 . .
C24 C25 H25C 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
C24 C26 H26A 109.5 . .
C24 C26 H26B 109.5 . .
H26A C26 H26B 109.5 . .
C24 C26 H26C 109.5 . .
H26A C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
C28 C27 C21 110.9(3) . .
C28 C27 C29 117.7(4) . .
C21 C27 C29 107.9(3) . .
C28 C27 H27 106.6 . .
C21 C27 H27 106.6 . .
C29 C27 H27 106.6 . .
C27 C28 H28A 109.5 . .
C27 C28 H28B 109.5 . .
H28A C28 H28B 109.5 . .
C27 C28 H28C 109.5 . .
H28A C28 H28C 109.5 . .
H28B C28 H28C 109.5 . .
C27 C29 H29A 109.5 . .
C27 C29 H29B 109.5 . .
H29A C29 H29B 109.5 . .
C27 C29 H29C 109.5 . .
H29A C29 H29C 109.5 . .
H29B C29 H29C 109.5 . .
C32 C30 C21 113.5(6) . .
C32 C30 C31 116.0(9) . .
C21 C30 C31 110.3(6) . .
C32 C30 H30 105.3 . .
C21 C30 H30 105.3 . .
C31 C30 H30 105.3 . .
C30 C31 H31A 109.5 . .
C30 C31 H31B 109.5 . .
H31A C31 H31B 109.5 . .
C30 C31 H31C 109.5 . .
H31A C31 H31C 109.5 . .
H31B C31 H31C 109.5 . .
C30 C32 H32A 109.5 . .
C30 C32 H32B 109.5 . .
H32A C32 H32B 109.5 . .
C30 C32 H32C 109.5 . .
H32A C32 H32C 109.5 . .
H32B C32 H32C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N11 C11 1.3497(17) .
N11 C12 1.364(2) .
N11 H11 0.90(2) .
N12 C11 1.3194(18) .
N12 C13 1.376(2) .
N21 C21 1.3413(18) .
N21 C22 1.363(2) .
N21 H21 0.87(2) .
N22 C21 1.3229(19) .
N22 C23 1.375(2) .
C11 C14 1.497(2) .
C12 C13 1.347(2) .
C12 H12 0.9500 .
C13 H13 0.9500 .
C14 C16 1.500(3) .
C14 C15 1.515(3) .
C14 H14 1.0000 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
C21 C30 1.501(2) .
C21 C24 1.501(2) .
C21 C27 1.501(2) .
C22 C23 1.346(2) .
C22 H22 0.9500 .
C23 H23 0.9500 .
C24 C26 1.459(5) .
C24 C25 1.520(5) .
C24 H24 1.0000 .
C25 H25A 0.9800 .
C25 H25B 0.9800 .
C25 H25C 0.9800 .
C26 H26A 0.9800 .
C26 H26B 0.9800 .
C26 H26C 0.9800 .
C27 C28 1.486(7) .
C27 C29 1.559(7) .
C27 H27 1.0000 .
C28 H28A 0.9800 .
C28 H28B 0.9800 .
C28 H28C 0.9800 .
C29 H29A 0.9800 .
C29 H29B 0.9800 .
C29 H29C 0.9800 .
C30 C32 1.420(13) .
C30 C31 1.558(12) .
C30 H30 1.0000 .
C31 H31A 0.9800 .
C31 H31B 0.9800 .
C31 H31C 0.9800 .
C32 H32A 0.9800 .
C32 H32B 0.9800 .
C32 H32C 0.9800 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N11 H11 N22 0.90(2) 1.95(2) 2.8382(17) 172(2) .
N21 H21 N12 0.87(2) 1.99(2) 2.8645(17) 173(2) 1_665
C12 H12 <i>C<i>~g~(1) 0.95 2.69 3.4991(17) 144 2_665
C16 H16B <i>C<i>~g~(1) 0.98 2.87 3.829(2) 167 2_666
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
C13 N12 C11 N11 0.34(17) . . . .
C13 N12 C11 C14 -177.44(15) . . . .
C12 N11 C11 N12 -0.08(17) . . . .
C12 N11 C11 C14 177.81(14) . . . .
C11 N11 C12 C13 -0.22(18) . . . .
N11 C12 C13 N12 0.44(19) . . . .
C11 N12 C13 C12 -0.49(19) . . . .
N12 C11 C14 C16 -13.0(3) . . . .
N11 C11 C14 C16 169.49(19) . . . .
N12 C11 C14 C15 112.4(2) . . . .
N11 C11 C14 C15 -65.1(2) . . . .
C23 N22 C21 N21 0.55(18) . . . .
C23 N22 C21 C30 -179.01(18) . . . .
C23 N22 C21 C24 -179.01(18) . . . .
C23 N22 C21 C27 -179.01(18) . . . .
C22 N21 C21 N22 -0.72(18) . . . .
C22 N21 C21 C30 178.87(17) . . . .
C22 N21 C21 C24 178.87(17) . . . .
C22 N21 C21 C27 178.87(17) . . . .
C21 N21 C22 C23 0.58(17) . . . .
N21 C22 C23 N22 -0.25(18) . . . .
C21 N22 C23 C22 -0.18(18) . . . .
N22 C21 C24 C26 21.3(4) . . . .
N21 C21 C24 C26 -158.2(4) . . . .
N22 C21 C24 C25 -108.2(3) . . . .
N21 C21 C24 C25 72.3(3) . . . .
N22 C21 C27 C28 -83.6(4) . . . .
N21 C21 C27 C28 96.9(4) . . . .
N22 C21 C27 C29 46.7(5) . . . .
N21 C21 C27 C29 -132.8(4) . . . .
N22 C21 C30 C32 86.3(8) . . . .
N21 C21 C30 C32 -93.2(8) . . . .
N22 C21 C30 C31 -45.8(7) . . . .
N21 C21 C30 C31 134.6(7) . . . .
