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

data_7224786
_publ_section_title
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 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                67.00(2)
_cell_angle_beta                 81.82(2)
_cell_angle_gamma                71.19(2)
_cell_formula_units_Z            2
_cell_length_a                   7.081(2)
_cell_length_b                   8.559(2)
_cell_length_c                   9.604(3)
_cell_measurement_reflns_used    1034
_cell_measurement_temperature    296
_cell_measurement_theta_max      29.3339
_cell_measurement_theta_min      2.6988
_cell_volume                     507.1(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_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_area_resol_mean 8.1929
_diffrn_measured_fraction_theta_full 0.277
_diffrn_measured_fraction_theta_max 0.221
_diffrn_measurement_details
;
  1 phi    -35.00   19.75   0.7500   29.0000
omega____ theta____ kappa____ phi______ frames
   0.0000  -30.0000    0.0000     -     73

  2 phi    140.00  200.00   0.7500   29.0000
omega____ theta____ kappa____ phi______ frames
   0.0000  -30.0000    0.0000     -     80

  3 phi    160.00  217.00   0.7500   29.0000
omega____ theta____ kappa____ phi______ frames
   0.0000   30.0000    0.0000     -     76

  4 phi    -20.00   34.75   0.7500   29.0000
omega____ theta____ kappa____ phi______ frames
   0.0000   30.0000    0.0000     -     73

  5 omega  -24.00   24.00   0.7500   29.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   39.4600  -12.9000 64

  6 omega  -24.00   24.00   0.7500   29.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   39.4600  167.1000 64

  7 omega  -50.00   10.00   0.7500   29.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000   39.4600  167.1000 80

  8 omega  -50.00   10.00   0.7500   29.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000   39.4600  -12.9000 80

  9 omega  -64.00   -8.50   0.7500   29.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000   81.4000  -28.9000 74

 10 omega  -64.00   -8.50   0.7500   29.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000   81.4000  151.1000 74

 11 omega  -19.00    8.00   0.7500   29.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   81.4000  151.1000 36

 12 omega  -19.00    8.00   0.7500   29.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   81.4000  -28.9000 36

 13 omega  -43.00  -21.25   0.7500   29.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  134.6000  -56.9000 29

 14 omega  -43.00  -21.25   0.7500   29.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  134.6000  123.1000 29

 15 omega  -90.00  -36.00   0.7500   29.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000  134.6000  123.1000 72

 16 omega  -90.00  -36.00   0.7500   29.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000  134.6000  -56.9000 72
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       '\w and \p scans'
_diffrn_orient_matrix_UB_11      -0.0804246000
_diffrn_orient_matrix_UB_12      0.0353132000
_diffrn_orient_matrix_UB_13      -0.0504249000
_diffrn_orient_matrix_UB_21      0.0410375000
_diffrn_orient_matrix_UB_22      -0.0707744000
_diffrn_orient_matrix_UB_23      -0.0266180000
_diffrn_orient_matrix_UB_31      -0.0552375000
_diffrn_orient_matrix_UB_32      -0.0511066000
_diffrn_orient_matrix_UB_33      0.0564834000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1837
_diffrn_reflns_av_unetI/netI     0.0938
_diffrn_reflns_Laue_measured_fraction_full 0.277
_diffrn_reflns_Laue_measured_fraction_max 0.221
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3791
_diffrn_reflns_point_group_measured_fraction_full 0.277
_diffrn_reflns_point_group_measured_fraction_max 0.221
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.400
_diffrn_reflns_theta_min         2.704
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.05506
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_description       plate
_exptl_crystal_F_000             208
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.27(9)
_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   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         620
_refine_ls_number_restraints     197
_refine_ls_restrained_S_all      0.951
_refine_ls_R_factor_all          0.1535
_refine_ls_R_factor_gt           0.0905
_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^)+(0.1530P)^2^+0.2770P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2311
_refine_ls_wR_factor_ref         0.3014
_reflns_Friedel_coverage         0.000
_reflns_number_gt                316
_reflns_number_total             620
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ce00419a2.cif
_cod_data_source_block           dMBzIm_EtOH_0_84GPa
_cod_depositor_comments
'Adding full bibliography for 7224786--7224795.cif.'
_cod_database_code               7224786
_chemical_oxdiff_formula         C9H10N2
_reflns_odcompleteness_completeness 26.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Rigid bond restraints
 N1, N3, C2, C4, C5, C6, C7, C8, C9, C10, C11
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 N1, N3, C2, C4, C5, C6, C7, C8, C9, C10, C11
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
N1 \\sim N3 \\sim C2 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim H7 \\sim C8
\\sim C9 \\sim C10 \\sim H10A \\sim C11: within 1.7A with sigma of 0.04 and
sigma for terminal atoms of 0.08
Uanis(O1) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C13) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C10) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C8) \\sim
Ueq, Uanis(N3) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(N1)
\\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C11) \\sim Ueq: with
sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C11) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C8) \\sim
Ueq, Uanis(N3) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(N1)
\\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C10) \\sim Ueq: with
sigma of 0.1 and sigma for terminal atoms of 0.2
4.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
4.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C2(H2), C4(H4), C7(H7)
4.c Fitted hexagon refined as free rotating group:
 C9(C4,C5,C6,C7,C8)
4.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
4.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              24849
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'