Pressure-induced preference for solvation of 5,6-dimethylbenzimidazole
Zielinski, Witold; Katrusiak, Andrzej; CrystEngComm 18 (2016) 3211–; doi:10.1039/C6CE00419A

data_7224789
_publ_section_title
;
 Pressure-induced preference for solvation of 5,6-dimethylbenzimidazole
;
_journal_issue                   18
_journal_name_full               CrystEngComm
_journal_page_first              3211
_journal_paper_doi               10.1039/C6CE00419A
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C2 H6 O, C9 H10 N2'
_chemical_formula_sum            'C11 H16 N2 O'
_chemical_formula_weight         192.26
_chemical_name_common            '5,6-dimethylbenzimidazole ethanol solvate'
_chemical_name_systematic        '5,6-dimethylbenzimidazole ethanol solvate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-03-29
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-03-29 deposited with the CCDC.
2016-04-01 downloaded from the CCDC.
;
_cell_angle_alpha                66.57(5)
_cell_angle_beta                 81.99(4)
_cell_angle_gamma                72.07(5)
_cell_formula_units_Z            2
_cell_length_a                   6.926(3)
_cell_length_b                   8.343(4)
_cell_length_c                   9.223(4)
_cell_measurement_reflns_used    1316
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.9710
_cell_measurement_theta_min      3.5870
_cell_volume                     465.2(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0593
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.367
_diffrn_measured_fraction_theta_max 0.241
_diffrn_measurement_details
;
  1 phi    -35.00   19.75   0.7500   35.0000
omega____ theta____ kappa____ phi______ frames
   0.0000  -30.0000    0.0000     -     73

  2 phi    140.00  200.00   0.7500   35.0000
omega____ theta____ kappa____ phi______ frames
   0.0000  -30.0000    0.0000     -     80

  3 phi    160.00  217.00   0.7500   35.0000
omega____ theta____ kappa____ phi______ frames
   0.0000   30.0000    0.0000     -     76

  4 phi    -20.00   34.75   0.7500   35.0000
omega____ theta____ kappa____ phi______ frames
   0.0000   30.0000    0.0000     -     73

  5 omega  -16.00   32.00   0.7500   35.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   39.4600  -12.9000 64

  6 omega  -16.00   32.00   0.7500   35.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   39.4600  167.1000 64

  7 omega  -50.00   10.00   0.7500   35.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000   39.4600  167.1000 80

  8 omega  -50.00   10.00   0.7500   35.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000   39.4600  -12.9000 80

  9 omega  -64.00   -8.50   0.7500   35.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000   81.4000  -28.9000 74

 10 omega  -64.00   -8.50   0.7500   35.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000   81.4000  151.1000 74

 11 omega  -12.00   15.00   0.7500   35.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   81.4000  151.1000 36

 12 omega  -12.00   15.00   0.7500   35.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   81.4000  -28.9000 36

 13 omega  -43.00  -21.25   0.7500   35.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  134.6000  -56.9000 29

 14 omega  -43.00  -21.25   0.7500   35.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  134.6000  123.1000 29

 15 omega  -90.00  -36.00   0.7500   35.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000  134.6000  123.1000 72

 16 omega  -90.00  -36.00   0.7500   35.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000  134.6000  -56.9000 72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, EosS2'
_diffrn_measurement_method       '\w and \p scans'
_diffrn_orient_matrix_UB_11      0.0254499000
_diffrn_orient_matrix_UB_12      -0.0760166000
_diffrn_orient_matrix_UB_13      0.0265891000
_diffrn_orient_matrix_UB_21      0.0802134000
_diffrn_orient_matrix_UB_22      0.0020524000
_diffrn_orient_matrix_UB_23      -0.0013069000
_diffrn_orient_matrix_UB_31      -0.0112527000
_diffrn_orient_matrix_UB_32      0.0021449000
_diffrn_orient_matrix_UB_33      0.0605192000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56085
_diffrn_reflns_av_R_equivalents  0.1460
_diffrn_reflns_av_unetI/netI     0.1175
_diffrn_reflns_Laue_measured_fraction_full 0.367
_diffrn_reflns_Laue_measured_fraction_max 0.241
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7509
_diffrn_reflns_point_group_measured_fraction_full 0.367
_diffrn_reflns_point_group_measured_fraction_max 0.241
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         30.161
_diffrn_reflns_theta_min         3.601
_diffrn_source                   'Enhance (Ag) X-ray Source'
_exptl_absorpt_coefficient_mu    0.057
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24156
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_description       plate
_exptl_crystal_F_000             208
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       0.4(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1350
_refine_ls_number_restraints     84
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.2012
_refine_ls_R_factor_gt           0.1112
_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/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2820
_refine_ls_wR_factor_ref         0.3637
_reflns_Friedel_coverage         0.000
_reflns_number_gt                611
_reflns_number_total             1350
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ce00419a2.cif
_cod_data_source_block           dMBzIm_EtOH_2_17GPa
_cod_depositor_comments
'Adding full bibliography for 7224786--7224795.cif.'
_cod_database_code               7224789
_chemical_oxdiff_formula         'C10 H14 N2 O1'
_reflns_odcompleteness_completeness 24.47
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.07
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C2) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(N3) \\sim Ueq, Uanis(C12)
\\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C10) \\sim Ueq,
Uanis(C7) \\sim Ueq, Uanis(O1) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C9) \\sim
Ueq, Uanis(C8) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C5) \\sim Ueq: with sigma
of 0.007 and sigma for terminal atoms of 0.012
3.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C4(H4), C7(H7)
3.c Fitted hexagon refined as free rotating group:
 C8(C9,C4,C5,C6,C7)
3.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
3.e Idealised tetrahedral OH refined as rotating group:
 O1(H1A)
;
_shelx_res_checksum              39089
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'