# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_dMBzIm_EtOH_0_84GPa
_database_code_depnum_ccdc_archive 'CCDC 1451562'
_audit_update_record             
;
2016-03-29 deposited with the CCDC.
2016-04-01 downloaded from the CCDC.
;
_audit_creation_date             2016-03-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            '5,6-dimethylbenzimidazole ethanol solvate'
_chemical_name_systematic        '5,6-dimethylbenzimidazole ethanol solvate'
_chemical_formula_moiety         'C2 H6 O, C9 H10 N2'
_chemical_formula_sum            'C11 H16 N2 O'
_chemical_formula_weight         192.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         C9H10N2
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'
O O 0.0106 0.0060 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.081(2)
_cell_length_b                   8.559(2)
_cell_length_c                   9.604(3)
_cell_angle_alpha                67.00(2)
_cell_angle_beta                 81.82(2)
_cell_angle_gamma                71.19(2)
_cell_volume                     507.1(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1034
_cell_measurement_temperature    296
_cell_measurement_theta_max      29.3339
_cell_measurement_theta_min      2.6988
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_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_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_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
_exptl_special_details           
;
 Data were collected at room temperature and pressure of 0.84(2) GPa
 (840000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique.
 Pressure was determined by monitoring the shift of the ruby
 R1-fluorescence line.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_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      
;
#__ type_ start__ end____ width___ exp.time_
  1 phi    -35.00   19.75   0.7500   29.0000
omega____ theta____ kappa____ phi______ frames
   0.0000  -30.0000    0.0000     -     73

#__ type_ start__ end____ width___ exp.time_
  2 phi    140.00  200.00   0.7500   29.0000
omega____ theta____ kappa____ phi______ frames
   0.0000  -30.0000    0.0000     -     80

#__ type_ start__ end____ width___ exp.time_
  3 phi    160.00  217.00   0.7500   29.0000
omega____ theta____ kappa____ phi______ frames
   0.0000   30.0000    0.0000     -     76

#__ type_ start__ end____ width___ exp.time_
  4 phi    -20.00   34.75   0.7500   29.0000
omega____ theta____ kappa____ phi______ frames
   0.0000   30.0000    0.0000     -     73

#__ type_ start__ end____ width___ exp.time_
  5 omega  -24.00   24.00   0.7500   29.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   39.4600  -12.9000 64

#__ type_ start__ end____ width___ exp.time_
  6 omega  -24.00   24.00   0.7500   29.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   39.4600  167.1000 64

#__ type_ start__ end____ width___ exp.time_
  7 omega  -50.00   10.00   0.7500   29.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000   39.4600  167.1000 80

#__ type_ start__ end____ width___ exp.time_
  8 omega  -50.00   10.00   0.7500   29.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000   39.4600  -12.9000 80

#__ type_ start__ end____ width___ exp.time_
  9 omega  -64.00   -8.50   0.7500   29.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000   81.4000  -28.9000 74

#__ type_ start__ end____ width___ exp.time_
 10 omega  -64.00   -8.50   0.7500   29.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000   81.4000  151.1000 74

#__ type_ start__ end____ width___ exp.time_
 11 omega  -19.00    8.00   0.7500   29.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   81.4000  151.1000 36

#__ type_ start__ end____ width___ exp.time_
 12 omega  -19.00    8.00   0.7500   29.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   81.4000  -28.9000 36

#__ type_ start__ end____ width___ exp.time_
 13 omega  -43.00  -21.25   0.7500   29.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  134.6000  -56.9000 29

#__ type_ start__ end____ width___ exp.time_
 14 omega  -43.00  -21.25   0.7500   29.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  134.6000  123.1000 29

#__ type_ start__ end____ width___ exp.time_
 15 omega  -90.00  -36.00   0.7500   29.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000  134.6000  123.1000 72

#__ type_ start__ end____ width___ exp.time_
 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       'ω and π 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_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                316
_reflns_number_total             620
_reflns_odcompleteness_completeness 26.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       
;
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)'
_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+0.001xFc²λ³/sin(2θ)]^-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_R_factor_all          0.1535
_refine_ls_R_factor_gt           0.0905
_refine_ls_restrained_S_all      0.951
_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)+(0.1530P)²+0.2770P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2311
_refine_ls_wR_factor_ref         0.3014
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O1 O 0.0408(18) 0.2547(10) 0.1567(12) 0.083(9) Uani 1 1 d . U . . .
H1 H -0.0763 0.2967 0.1772 0.125 Uiso 1 1 calc GR . . . .
C12 C 0.055(3) 0.2486(15) 0.008(2) 0.074(6) Uani 1 1 d . U . . .
H12A H 0.0825 0.3553 -0.0658 0.088 Uiso 1 1 calc R . . . .
H12B H -0.0703 0.2441 -0.0169 0.088 Uiso 1 1 calc R . . . .
C13 C 0.216(3) 0.0913(16) 0.001(2) 0.093(10) Uani 1 1 d . U . . .
H13A H 0.3425 0.1016 0.0161 0.140 Uiso 1 1 calc GR . . . .
H13B H 0.2174 0.0835 -0.0960 0.140 Uiso 1 1 calc GR . . . .
H13C H 0.1944 -0.0136 0.0789 0.140 Uiso 1 1 calc GR . . . .
N1 N 0.646(2) 0.3990(12) 0.1875(15) 0.060(5) Uani 1 1 d . U . . .
N3 N 0.345(2) 0.3584(12) 0.2086(15) 0.059(4) Uani 1 1 d . U . . .
H3 H 0.2542 0.3151 0.2028 0.071 Uiso 1 1 calc R . . . .
C2 C 0.536(3) 0.3156(17) 0.163(2) 0.066(5) Uani 1 1 d . U . . .
H2 H 0.5866 0.2327 0.1166 0.079 Uiso 1 1 calc R . . . .
C9 C 0.3258(14) 0.4862(9) 0.2671(10) 0.052(4) Uani 1 1 d . U . . .
C4 C 0.1657(13) 0.5838(8) 0.3297(10) 0.052(5) Uani 1 1 d G U . . .
H4 H 0.0408 0.5664 0.3381 0.062 Uiso 1 1 calc R . . . .
C5 C 0.1921(14) 0.7072(8) 0.3797(11) 0.051(4) Uani 1 1 d G U . . .
C6 C 0.3787(14) 0.7331(9) 0.3671(10) 0.056(4) Uani 1 1 d G U . . .
C7 C 0.5388(13) 0.6355(8) 0.3046(10) 0.055(4) Uani 1 1 d G U . . .
H7 H 0.6637 0.6529 0.2962 0.066 Uiso 1 1 calc R U . . .
C8 C 0.5124(13) 0.5121(8) 0.2546(11) 0.051(4) Uani 1 1 d G U . . .
C10 C 0.022(3) 0.8111(15) 0.4472(18) 0.057(8) Uani 1 1 d . U . . .
H10A H -0.0108 0.9342 0.3826 0.085 Uiso 1 1 calc GR U . . .
H10B H 0.0579 0.7974 0.5448 0.085 Uiso 1 1 calc GR . . . .
H10C H -0.0915 0.7688 0.4577 0.085 Uiso 1 1 calc GR . . . .
C11 C 0.408(3) 0.8703(14) 0.4195(18) 0.055(8) Uani 1 1 d . U . . .
H11A H 0.3356 0.9872 0.3549 0.082 Uiso 1 1 calc GR . . . .
H11B H 0.5470 0.8609 0.4149 0.082 Uiso 1 1 calc GR . . . .
H11C H 0.3587 0.8494 0.5217 0.082 Uiso 1 1 calc GR . . . .

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
O1 0.090(16) 0.085(6) 0.098(13) -0.056(8) 0.026(13) -0.039(9)
C12 0.090(11) 0.069(6) 0.060(10) -0.030(6) -0.001(9) -0.014(7)
C13 0.11(2) 0.085(8) 0.090(16) -0.052(10) 0.013(16) -0.022(11)
N1 0.059(8) 0.058(5) 0.068(8) -0.027(5) -0.001(7) -0.019(5)
N3 0.065(8) 0.057(4) 0.066(8) -0.030(5) -0.001(7) -0.022(5)
C2 0.065(9) 0.066(5) 0.078(9) -0.037(6) 0.000(7) -0.020(6)
C9 0.057(8) 0.045(5) 0.056(8) -0.018(5) -0.004(7) -0.018(5)
C4 0.059(9) 0.054(5) 0.051(9) -0.022(5) -0.003(7) -0.023(6)
C5 0.055(8) 0.051(5) 0.050(8) -0.021(5) 0.005(7) -0.022(5)
C6 0.063(8) 0.053(5) 0.063(8) -0.024(5) 0.000(7) -0.025(6)
C7 0.055(8) 0.056(5) 0.059(8) -0.017(5) -0.001(7) -0.029(5)
C8 0.057(8) 0.043(5) 0.049(8) -0.009(5) -0.006(7) -0.016(5)
C10 0.059(14) 0.065(7) 0.061(14) -0.035(8) -0.006(13) -0.018(8)
C11 0.070(15) 0.038(6) 0.049(13) -0.004(8) -0.032(12) -0.009(9)

_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
O1 H1 0.8200 . ?
O1 C12 1.438(17) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.475(19) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
N1 C2 1.31(2) . ?
N1 C8 1.403(7) . ?
N3 H3 0.8600 . ?
N3 C2 1.336(18) . ?
N3 C9 1.375(8) . ?
C2 H2 0.9300 . ?
C9 C4 1.3900 . ?
C9 C8 1.3900 . ?
C4 H4 0.9300 . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C5 C10 1.483(9) . ?
C6 C7 1.3900 . ?
C6 C11 1.523(12) . ?
C7 H7 0.9300 . ?
C7 C8 1.3900 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

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
C12 O1 H1 109.5 . . ?
O1 C12 H12A 109.6 . . ?
O1 C12 H12B 109.6 . . ?
O1 C12 C13 110.4(16) . . ?
H12A C12 H12B 108.1 . . ?
C13 C12 H12A 109.6 . . ?
C13 C12 H12B 109.6 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C2 N1 C8 104.0(10) . . ?
C2 N3 H3 127.2 . . ?
C2 N3 C9 105.7(10) . . ?
C9 N3 H3 127.2 . . ?
N1 C2 N3 115.0(8) . . ?
N1 C2 H2 122.5 . . ?
N3 C2 H2 122.5 . . ?
N3 C9 C4 133.2(7) . . ?
N3 C9 C8 106.8(7) . . ?
C4 C9 C8 120.0 . . ?
C9 C4 H4 120.0 . . ?
C5 C4 C9 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C10 120.2(7) . . ?
C6 C5 C4 120.0 . . ?
C6 C5 C10 119.8(7) . . ?
C5 C6 C11 120.2(7) . . ?
C7 C6 C5 120.0 . . ?
C7 C6 C11 119.8(7) . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C8 120.0 . . ?
C8 C7 H7 120.0 . . ?
C9 C8 N1 108.5(7) . . ?
C7 C8 N1 131.5(7) . . ?
C7 C8 C9 120.0 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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
N3 C9 C4 C5 -179.7(12) . . . . ?
N3 C9 C8 N1 0.1(10) . . . . ?
N3 C9 C8 C7 179.8(9) . . . . ?
C2 N1 C8 C9 0.6(12) . . . . ?
C2 N1 C8 C7 -178.9(11) . . . . ?
C2 N3 C9 C4 178.9(11) . . . . ?
C2 N3 C9 C8 -0.8(13) . . . . ?
C9 N3 C2 N1 1.3(19) . . . . ?
C9 C4 C5 C6 0.0 . . . . ?
C9 C4 C5 C10 -179.7(10) . . . . ?
C4 C9 C8 N1 -179.6(9) . . . . ?
C4 C9 C8 C7 0.0 . . . . ?
C4 C5 C6 C7 0.0 . . . . ?
C4 C5 C6 C11 179.0(10) . . . . ?
C5 C6 C7 C8 0.0 . . . . ?
C6 C7 C8 N1 179.5(11) . . . . ?
C6 C7 C8 C9 0.0 . . . . ?
C8 N1 C2 N3 -1.2(18) . . . . ?
C8 C9 C4 C5 0.0 . . . . ?
C10 C5 C6 C7 179.7(10) . . . . ?
C10 C5 C6 C11 -1.3(12) . . . . ?
C11 C6 C7 C8 -179.0(10) . . . . ?

_shelx_res_file                  
;
    35.res created by SHELXL-2014/7

TITL 35 in P-1 #2
REM reset to P-1 #2
CELL 0.71073 7.081276 8.558682 9.603689 67.0001 81.8209 71.1916
ZERR 2 0.002006 0.002 0.002515 0.0234 0.0225 0.0232
LATT 1
SFAC C H N O
UNIT 22 32 4 2
DELU N1 N3 C2 C4 > C8 C9 C10 C11
DELU N1 N3 C2 C4 > C8 C9 C10 C11
SIMU 0.04 0.08 1.7 N1 N3 C2 C4 > C7 H7 C8 C9 C10 H10a C11
ISOR 0.01 0.02 O1 C12 C13
ISOR 0.01 0.02 C10 C9 C4 C8 N3 C5 C7 N1 C2 C6 C11
ISOR C11 C9 C4 C8 N3 C5 C7 N1 C2 C6 C10

L.S. 44
PLAN  5
BOND $h
fmap 2
acta
MORE -1
CONF
OMIT -1 4 5
OMIT 0 2 4
OMIT -2 -2 4
OMIT -3 2 9
OMIT -2 -5 3
OMIT 3 10 0
OMIT -1 -2 3
OMIT -3 -4 5
OMIT -4 2 7
OMIT 0 1 1
OMIT 3 5 2
REM <olex2.extras>
REM <HklSrc "%.\\35.hkl">
REM </olex2.extras>

WGHT    0.153000    0.277000
EXTI    0.270243
FVAR       3.07881
O1    4    0.040805    0.254718    0.156720    11.00000    0.09024    0.08455 =
         0.09754   -0.05573    0.02622   -0.03895
AFIX 147
H1    2   -0.076322    0.296696    0.177214    11.00000   -1.50000
AFIX   0
C12   1    0.055439    0.248643    0.007937    11.00000    0.08999    0.06930 =
         0.06041   -0.02961   -0.00115   -0.01439
AFIX  23
H12A  2    0.082489    0.355314   -0.065848    11.00000   -1.20000
H12B  2   -0.070315    0.244124   -0.016853    11.00000   -1.20000
AFIX   0
C13   1    0.216472    0.091294    0.001147    11.00000    0.11402    0.08513 =
         0.09025   -0.05244    0.01339   -0.02233
AFIX 137
H13A  2    0.342496    0.101570    0.016082    11.00000   -1.50000
H13B  2    0.217368    0.083479   -0.095991    11.00000   -1.50000
H13C  2    0.194362   -0.013583    0.078933    11.00000   -1.50000
AFIX   0

N1    3    0.645679    0.398953    0.187471    11.00000    0.05907    0.05806 =
         0.06844   -0.02708   -0.00085   -0.01859
N3    3    0.345482    0.358407    0.208616    11.00000    0.06521    0.05735 =
         0.06599   -0.03050   -0.00142   -0.02219
AFIX  43
H3    2    0.254195    0.315081    0.202784    11.00000   -1.20000
AFIX   0
C2    1    0.535872    0.315573    0.162706    11.00000    0.06459    0.06625 =
         0.07793   -0.03706   -0.00007   -0.02048
AFIX  43
H2    2    0.586627    0.232663    0.116574    11.00000   -1.20000
AFIX  66
C9    1    0.325835    0.486171    0.267130    11.00000    0.05685    0.04516 =
         0.05600   -0.01761   -0.00449   -0.01801
C4    1    0.165666    0.583760    0.329667    11.00000    0.05881    0.05384 =
         0.05082   -0.02225   -0.00328   -0.02299
AFIX  43
H4    2    0.040825    0.566438    0.338055    11.00000   -1.20000
AFIX  65
C5    1    0.192085    0.707239    0.379668    11.00000    0.05517    0.05143 =
         0.04990   -0.02053    0.00530   -0.02163
C6    1    0.378674    0.733130    0.367133    11.00000    0.06261    0.05275 =
         0.06262   -0.02402    0.00013   -0.02543
C7    1    0.538845    0.635542    0.304596    11.00000    0.05521    0.05626 =
         0.05896   -0.01710   -0.00095   -0.02938
AFIX  43
H7    2    0.663686    0.652866    0.296209    11.00000   -1.20000
AFIX  65
C8    1    0.512429    0.512062    0.254594    11.00000    0.05668    0.04288 =
         0.04884   -0.00930   -0.00592   -0.01639
AFIX   0
C10   1    0.021916    0.811055    0.447163    11.00000    0.05895    0.06457 =
         0.06075   -0.03544   -0.00554   -0.01819
AFIX 137
H10A  2   -0.010815    0.934193    0.382601    11.00000   -1.50000
H10B  2    0.057877    0.797424    0.544834    11.00000   -1.50000
H10C  2   -0.091476    0.768755    0.457748    11.00000   -1.50000
AFIX   0
C11   1    0.407662    0.870342    0.419494    11.00000    0.06999    0.03785 =
         0.04914   -0.00397   -0.03168   -0.00944
AFIX 137
H11A  2    0.335563    0.987173    0.354887    11.00000   -1.50000
H11B  2    0.547032    0.860938    0.414897    11.00000   -1.50000
H11C  2    0.358659    0.849388    0.521695    11.00000   -1.50000
AFIX   0
HKLF 4

REM  35 in P-1 #2
REM R1 =  0.0905 for     316 Fo > 4sig(Fo)  and  0.1535 for all     620 data
REM    120 parameters refined using    197 restraints

END

WGHT      0.1516      0.2773

REM Highest difference peak  0.177,  deepest hole -0.139,  1-sigma level  0.041
Q1    1  -0.0031  0.1533  0.1158  11.00000  0.05    0.18
Q2    1   0.3638  0.5139  0.2525  11.00000  0.05    0.17
Q3    1   0.3222  0.5442  0.2255  11.00000  0.05    0.17
Q4    1   0.3237  0.4825  0.4386  11.00000  0.05    0.17
Q5    1   0.3569  0.4614  0.4648  11.00000  0.05    0.16
;
_shelx_res_checksum              24849
_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_dMBzIm_EtOH_1_20GPa
_database_code_depnum_ccdc_archive 'CCDC 1451563'
_audit_update_record             
;
2016-03-29 deposited with the CCDC.
2016-04-01 downloaded from the CCDC.
;
_audit_creation_date             2016-03-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            '5,6-dimethylbenzimidazole ethanol solvate'
_chemical_name_systematic        '5,6-dimethylbenzimidazole ethanol solvate'
_chemical_formula_moiety         'C2 H6 O, C9 H10 N2'
_chemical_formula_sum            'C11 H16 N2 O'
_chemical_formula_weight         192.26
_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 0.0033 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'
O O 0.0106 0.0060 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0242(16)
_cell_length_b                   8.496(2)
_cell_length_c                   9.475(2)
_cell_angle_alpha                66.75(2)
_cell_angle_beta                 81.96(2)
_cell_angle_gamma                71.38(2)
_cell_volume                     492.3(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1048
_cell_measurement_temperature    296
_cell_measurement_theta_max      29.1569
_cell_measurement_theta_min      2.7854
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             208
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.35
_exptl_special_details           
;
 Data were collected at room temperature and pressure of 1.20(2) GPa
 (1200000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique.
 Pressure was determined by monitoring the shift of the ruby
 R1-fluorescence line.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1240
_diffrn_reflns_av_unetI/netI     0.0751
_diffrn_reflns_Laue_measured_fraction_full 0.272
_diffrn_reflns_Laue_measured_fraction_max 0.241
_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            3470
_diffrn_reflns_point_group_measured_fraction_full 0.272
_diffrn_reflns_point_group_measured_fraction_max 0.241
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.172
_diffrn_reflns_theta_min         3.459
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.272
_diffrn_measured_fraction_theta_max 0.241
_diffrn_measurement_device_type  'KUMA CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                344
_reflns_number_total             582
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         582
_refine_ls_number_restraints     168
_refine_ls_R_factor_all          0.1410
_refine_ls_R_factor_gt           0.0957
_refine_ls_restrained_S_all      0.992
_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)+(0.1880P)²+0.2360P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2530
_refine_ls_wR_factor_ref         0.3100
_refine_special_details          ?
_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
All non-hydrogen atoms have similar U: within 1.7A with sigma of 0.04 and sigma
for terminal atoms of 0.08
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.02 and sigma
for terminal atoms of 0.001
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:
 C5(C4,C9,C8,C7,C6)
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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O1 O 0.0459(18) 0.2497(10) 0.1606(12) 0.0540(18) Uani 1 1 d . U . . .
H1A H -0.0723 0.2651 0.1884 0.081 Uiso 1 1 calc GR . . . .
C12 C 0.066(3) 0.2437(15) 0.0124(19) 0.076(9) Uani 1 1 d . U . . .
H12A H 0.0989 0.3500 -0.0605 0.091 Uiso 1 1 calc R . . . .
H12B H -0.0609 0.2443 -0.0169 0.091 Uiso 1 1 calc R . . . .
C13 C 0.222(3) 0.0853(15) 0.005(2) 0.067(3) Uani 1 1 d . U . . .
H13A H 0.1939 -0.0202 0.0800 0.101 Uiso 1 1 calc GR . . . .
H13B H 0.3503 0.0895 0.0246 0.101 Uiso 1 1 calc GR . . . .
H13C H 0.2245 0.0825 -0.0959 0.101 Uiso 1 1 calc GR . . . .
N1 N 0.343(2) 0.3581(11) 0.2074(15) 0.052(7) Uani 1 1 d . U . . .
H1 H 0.2499 0.3166 0.1991 0.063 Uiso 1 1 calc R . . . .
N3 N 0.651(2) 0.3968(11) 0.1884(15) 0.058(7) Uani 1 1 d . U . . .
C2 C 0.537(3) 0.3147(14) 0.1622(19) 0.056(8) Uani 1 1 d . U . . .
H2 H 0.5872 0.2317 0.1152 0.067 Uiso 1 1 calc R . . . .
C5 C 0.3768(13) 0.7362(8) 0.3663(10) 0.051(7) Uani 1 1 d . U . . .
C4 C 0.5385(12) 0.6384(8) 0.3036(9) 0.043(8) Uani 1 1 d G U . . .
H4 H 0.6636 0.6576 0.2941 0.051 Uiso 1 1 calc R . . . .
C9 C 0.5132(13) 0.5118(8) 0.2552(10) 0.054(7) Uani 1 1 d G U . . .
C8 C 0.3262(13) 0.4831(8) 0.2695(10) 0.053(7) Uani 1 1 d G U . . .
C7 C 0.1645(12) 0.5809(8) 0.3322(9) 0.052(8) Uani 1 1 d G U . . .
H7 H 0.0394 0.5617 0.3418 0.062 Uiso 1 1 calc R . . . .
C6 C 0.1898(12) 0.7075(7) 0.3806(10) 0.047(7) Uani 1 1 d G U . . .
C10 C 0.408(3) 0.8736(14) 0.4186(18) 0.049(2) Uani 1 1 d . U . . .
H10A H 0.3459 0.9918 0.3473 0.073 Uiso 1 1 calc GR . . . .
H10B H 0.5489 0.8564 0.4229 0.073 Uiso 1 1 calc GR . . . .
H10C H 0.3477 0.8594 0.5187 0.073 Uiso 1 1 calc GR . . . .
C11 C 0.016(3) 0.8152(14) 0.4443(18) 0.046(2) Uani 1 1 d . U . . .
H11A H -0.0132 0.9391 0.3778 0.069 Uiso 1 1 calc GR . . . .
H11B H 0.0480 0.8016 0.5445 0.069 Uiso 1 1 calc GR . . . .
H11C H -0.0992 0.7746 0.4519 0.069 Uiso 1 1 calc GR . . . .

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
O1 0.054(2) 0.0552(18) 0.053(2) -0.0222(12) 0.0003(11) -0.0138(11)
C12 0.095(17) 0.072(7) 0.076(14) -0.046(9) 0.028(14) -0.034(9)
C13 0.067(3) 0.067(3) 0.067(3) -0.0258(14) -0.0009(11) -0.0187(13)
N1 0.056(14) 0.045(5) 0.061(10) -0.028(6) 0.011(11) -0.018(7)
N3 0.062(13) 0.053(5) 0.064(11) -0.032(7) 0.016(11) -0.019(7)
C2 0.072(14) 0.045(6) 0.048(12) -0.023(7) 0.014(12) -0.012(8)
C5 0.054(14) 0.040(5) 0.059(12) -0.020(7) 0.010(11) -0.016(7)
C4 0.047(14) 0.044(6) 0.034(12) -0.009(7) 0.005(12) -0.018(8)
C9 0.068(13) 0.047(5) 0.052(11) -0.026(7) 0.018(11) -0.020(7)
C8 0.063(13) 0.044(5) 0.056(11) -0.023(7) 0.019(11) -0.024(7)
C7 0.061(14) 0.051(6) 0.051(12) -0.025(7) 0.021(12) -0.028(8)
C6 0.052(13) 0.047(6) 0.046(11) -0.020(7) 0.009(11) -0.021(8)
C10 0.050(2) 0.048(2) 0.050(2) -0.0182(12) -0.0020(11) -0.0148(12)
C11 0.047(2) 0.047(2) 0.046(2) -0.0187(12) -0.0005(11) -0.0120(12)

_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
O1 H1A 0.8200 . ?
O1 C12 1.411(17) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.459(17) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
N1 H1 0.8600 . ?
N1 C2 1.347(17) . ?
N1 C8 1.372(8) . ?
N3 C2 1.319(19) . ?
N3 C9 1.416(6) . ?
C2 H2 0.9300 . ?
C5 C4 1.3900 . ?
C5 C6 1.3900 . ?
C5 C10 1.517(12) . ?
C4 H4 0.9300 . ?
C4 C9 1.3900 . ?
C9 C8 1.3900 . ?
C8 C7 1.3900 . ?
C7 H7 0.9300 . ?
C7 C6 1.3900 . ?
C6 C11 1.487(9) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

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
C12 O1 H1A 109.5 . . ?
O1 C12 H12A 109.1 . . ?
O1 C12 H12B 109.1 . . ?
O1 C12 C13 112.3(16) . . ?
H12A C12 H12B 107.9 . . ?
C13 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C2 N1 H1 127.6 . . ?
C2 N1 C8 104.8(11) . . ?
C8 N1 H1 127.6 . . ?
C2 N3 C9 102.6(9) . . ?
N1 C2 H2 121.9 . . ?
N3 C2 N1 116.1(7) . . ?
N3 C2 H2 121.9 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 C10 119.2(6) . . ?
C6 C5 C10 120.8(6) . . ?
C5 C4 H4 120.0 . . ?
C9 C4 C5 120.0 . . ?
C9 C4 H4 120.0 . . ?
C4 C9 N3 131.1(6) . . ?
C4 C9 C8 120.0 . . ?
C8 C9 N3 108.9(6) . . ?
N1 C8 C9 107.5(6) . . ?
N1 C8 C7 132.5(7) . . ?
C9 C8 C7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C6 C7 C8 120.0 . . ?
C6 C7 H7 120.0 . . ?
C5 C6 C11 119.9(7) . . ?
C7 C6 C5 120.0 . . ?
C7 C6 C11 120.1(7) . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

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
O1 H1A N3 0.82 1.91 2.678(16) 155.8 1_455
N1 H1 O1 0.86 1.83 2.684(17) 173.5 .

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
N1 C8 C7 C6 -176.7(11) . . . . ?
N3 C9 C8 N1 -2.4(10) . . . . ?
N3 C9 C8 C7 -179.9(8) . . . . ?
C2 N1 C8 C9 1.3(13) . . . . ?
C2 N1 C8 C7 178.3(10) . . . . ?
C2 N3 C9 C4 -177.4(9) . . . . ?
C2 N3 C9 C8 2.5(11) . . . . ?
C5 C4 C9 N3 179.9(10) . . . . ?
C5 C4 C9 C8 0.0 . . . . ?
C4 C5 C6 C7 0.0 . . . . ?
C4 C5 C6 C11 -178.6(9) . . . . ?
C4 C9 C8 N1 177.5(9) . . . . ?
C4 C9 C8 C7 0.0 . . . . ?
C9 N3 C2 N1 -1.8(16) . . . . ?
C9 C8 C7 C6 0.0 . . . . ?
C8 N1 C2 N3 0.3(17) . . . . ?
C8 C7 C6 C5 0.0 . . . . ?
C8 C7 C6 C11 178.6(9) . . . . ?
C6 C5 C4 C9 0.0 . . . . ?
C10 C5 C4 C9 179.9(10) . . . . ?
C10 C5 C6 C7 -179.9(10) . . . . ?
C10 C5 C6 C11 1.5(12) . . . . ?

_shelx_res_file                  
;
    36b.res created by SHELXL-2014/7

TITL 36b in P-1
REM P-1 (#2 in standard setting)
CELL 0.71073 7.024183 8.495998 9.475274 66.7451 81.962 71.3793
ZERR 2 0.001608 0.002098 0.002353 0.0236 0.0198 0.0218
LATT 1
SFAC C H N O
UNIT 22 32 4 2
EQIV $1 -1+X,+Y,+Z
SIMU 0.04 0.08 1.7
ISOR 0.02 0.001

L.S. 44
PLAN  10
TEMP 22.85
HTAB O1 N3_$1
HTAB N1 O1
BOND $H
MORE -1
CONF
fmap 2
acta 52
OMIT 0 2 4
OMIT -1 4 5
OMIT 1 4 1
OMIT -1 2 3
OMIT -2 5 4
OMIT -3 -4 5
OMIT -2 4 7
OMIT -3 -2 6
OMIT -1 1 3
OMIT 3 3 0
OMIT -5 0 4
OMIT -1 4 4
OMIT -3 3 6
OMIT -3 2 4
OMIT -3 5 6
OMIT -2 -2 4
OMIT -2 -5 3
OMIT -1 -4 2
OMIT -1 -2 3
OMIT -2 -1 4
OMIT 2 8 6
OMIT -4 -3 2
OMIT -2 3 8
OMIT 2 3 0
OMIT 3 6 2
OMIT -2 3 4
REM <olex2.extras>
REM <HklSrc "%.\\36b.hkl">
REM </olex2.extras>

WGHT    0.188000    0.236000
FVAR       8.99658
O1    4    0.045865    0.249675    0.160622    11.00000    0.05390    0.05524 =
         0.05302   -0.02220    0.00027   -0.01383
AFIX 147
H1A   2   -0.072330    0.265088    0.188406    11.00000   -1.50000
AFIX   0
C12   1    0.066307    0.243705    0.012379    11.00000    0.09497    0.07207 =
         0.07594   -0.04567    0.02845   -0.03441
AFIX  23
H12A  2    0.098925    0.350038   -0.060516    11.00000   -1.20000
H12B  2   -0.060899    0.244308   -0.016934    11.00000   -1.20000
AFIX   0
C13   1    0.222050    0.085349    0.004582    11.00000    0.06744    0.06737 =
         0.06681   -0.02582   -0.00085   -0.01871
AFIX 137
H13A  2    0.193864   -0.020192    0.079983    11.00000   -1.50000
H13B  2    0.350251    0.089536    0.024583    11.00000   -1.50000
H13C  2    0.224521    0.082498   -0.095950    11.00000   -1.50000
AFIX   0

N1    3    0.342785    0.358115    0.207375    11.00000    0.05630    0.04536 =
         0.06082   -0.02775    0.01072   -0.01751
AFIX  43
H1    2    0.249854    0.316635    0.199079    11.00000   -1.20000
AFIX   0
N3    3    0.650851    0.396778    0.188441    11.00000    0.06172    0.05335 =
         0.06378   -0.03178    0.01633   -0.01898
C2    1    0.536722    0.314719    0.162195    11.00000    0.07167    0.04494 =
         0.04759   -0.02251    0.01436   -0.01200
AFIX  43
H2    2    0.587186    0.231726    0.115231    11.00000   -1.20000
AFIX  66
C5    1    0.376770    0.736213    0.366337    11.00000    0.05396    0.04045 =
         0.05896   -0.02042    0.01017   -0.01605
C4    1    0.538478    0.638400    0.303637    11.00000    0.04699    0.04383 =
         0.03377   -0.00868    0.00477   -0.01782
AFIX  43
H4    2    0.663585    0.657635    0.294067    11.00000   -1.20000
AFIX  65
C9    1    0.513198    0.511837    0.255242    11.00000    0.06839    0.04714 =
         0.05186   -0.02648    0.01817   -0.02020
C8    1    0.326212    0.483087    0.269546    11.00000    0.06288    0.04435 =
         0.05608   -0.02294    0.01853   -0.02418
C7    1    0.164502    0.580899    0.332246    11.00000    0.06078    0.05108 =
         0.05092   -0.02524    0.02134   -0.02829
AFIX  43
H7    2    0.039395    0.561663    0.341816    11.00000   -1.20000
AFIX  65
C6    1    0.189778    0.707463    0.380642    11.00000    0.05157    0.04667 =
         0.04553   -0.01973    0.00897   -0.02066
AFIX   0
C10   1    0.407657    0.873587    0.418599    11.00000    0.04961    0.04770 =
         0.04959   -0.01825   -0.00202   -0.01480
AFIX 137
H10A  2    0.345896    0.991805    0.347252    11.00000   -1.50000
H10B  2    0.548901    0.856444    0.422927    11.00000   -1.50000
H10C  2    0.347713    0.859421    0.518679    11.00000   -1.50000
AFIX   0
C11   1    0.015949    0.815246    0.444335    11.00000    0.04661    0.04663 =
         0.04583   -0.01867   -0.00046   -0.01196
AFIX 137
H11A  2   -0.013182    0.939105    0.377750    11.00000   -1.50000
H11B  2    0.047992    0.801647    0.544515    11.00000   -1.50000
H11C  2   -0.099216    0.774591    0.451871    11.00000   -1.50000
AFIX   0
HKLF 4

REM  36b in P-1
REM R1 =  0.0957 for     344 Fo > 4sig(Fo)  and  0.1410 for all     582 data
REM    119 parameters refined using    168 restraints

END

WGHT      0.1881      0.2349

REM Highest difference peak  0.210,  deepest hole -0.166,  1-sigma level  0.050
Q1    1   0.1885  1.1408  0.2840  11.00000  0.05    0.21
Q2    1  -0.1222  0.3442  0.0458  11.00000  0.05    0.20
Q3    1   0.3988  0.4810  0.2994  11.00000  0.05    0.20
Q4    1   0.3722  0.5259  0.2474  11.00000  0.05    0.20
Q5    1  -0.1541  0.3597  0.0175  11.00000  0.05    0.20
Q6    1   0.6507  0.9606  0.2813  11.00000  0.05    0.17
Q7    1   0.6041  0.9957  0.4211  11.00000  0.05    0.15
Q8    1   0.4411  0.5210  0.0614  11.00000  0.05    0.14
Q9    1   0.3326  0.4782  0.4576  11.00000  0.05    0.14
Q10   1   0.2798  0.4985  0.4203  11.00000  0.05    0.14
;
_shelx_res_checksum              51126
_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_dMBzIm_EtOH_1_50GPa
_database_code_depnum_ccdc_archive 'CCDC 1451564'
_audit_update_record             
;
2016-03-29 deposited with the CCDC.
2016-04-01 downloaded from the CCDC.
;
_audit_creation_date             2016-03-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            '5,6-dimethylbenzimidazole ethanol solvate'
_chemical_name_systematic        '5,6-dimethylbenzimidazole ethanol solvate'
_chemical_formula_moiety         'C2 H6 O, C9 H10 N2'
_chemical_formula_sum            'C11 H16 N2 O'
_chemical_formula_weight         192.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H16 N2 O1'
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'
O O 0.0106 0.0060 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0048(7)
_cell_length_b                   8.453(3)
_cell_length_c                   9.3834(12)
_cell_angle_alpha                66.49(2)
_cell_angle_beta                 81.840(9)
_cell_angle_gamma                71.705(18)
_cell_volume                     483.6(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    887
_cell_measurement_temperature    296
_cell_measurement_theta_max      26.4730
_cell_measurement_theta_min      3.9010
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.01700
_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_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             208
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 Data were collected at room temperature and pressure of 1.50(2) GPa
 (1500000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique.
 Pressure was determined by monitoring the shift of the ruby
 R1-fluorescence line.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_Laue_measured_fraction_full 0.292
_diffrn_reflns_Laue_measured_fraction_max 0.268
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2897
_diffrn_reflns_point_group_measured_fraction_full 0.292
_diffrn_reflns_point_group_measured_fraction_max 0.268
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.215
_diffrn_reflns_theta_min         3.909
_diffrn_ambient_temperature      296
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2413
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.292
_diffrn_measured_fraction_theta_max 0.268
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 phi    -35.00   19.75   0.7500   34.0000
omega____ theta____ kappa____ phi______ frames
   0.0000  -30.0000    0.0000     -     73

#__ type_ start__ end____ width___ exp.time_
  2 phi    140.00  200.00   0.7500   34.0000
omega____ theta____ kappa____ phi______ frames
   0.0000  -30.0000    0.0000     -     80

#__ type_ start__ end____ width___ exp.time_
  3 phi    160.00  217.00   0.7500   34.0000
omega____ theta____ kappa____ phi______ frames
   0.0000   30.0000    0.0000     -     76

#__ type_ start__ end____ width___ exp.time_
  4 phi    -20.00   34.75   0.7500   34.0000
omega____ theta____ kappa____ phi______ frames
   0.0000   30.0000    0.0000     -     73

#__ type_ start__ end____ width___ exp.time_
  5 omega  -24.00   24.00   0.7500   34.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   39.4600  -12.9000 64

#__ type_ start__ end____ width___ exp.time_
  6 omega  -24.00   24.00   0.7500   34.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   39.4600  167.1000 64

#__ type_ start__ end____ width___ exp.time_
  7 omega  -50.00   10.00   0.7500   34.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000   39.4600  167.1000 80

#__ type_ start__ end____ width___ exp.time_
  8 omega  -50.00   10.00   0.7500   34.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000   39.4600  -12.9000 80

#__ type_ start__ end____ width___ exp.time_
  9 omega  -64.00   -8.50   0.7500   34.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000   81.4000  -28.9000 74

#__ type_ start__ end____ width___ exp.time_
 10 omega  -64.00   -8.50   0.7500   34.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000   81.4000  151.1000 74

#__ type_ start__ end____ width___ exp.time_
 11 omega  -19.00    8.00   0.7500   34.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   81.4000  151.1000 36

#__ type_ start__ end____ width___ exp.time_
 12 omega  -19.00    8.00   0.7500   34.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   81.4000  -28.9000 36

#__ type_ start__ end____ width___ exp.time_
 13 omega  -43.00  -21.25   0.7500   34.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  134.6000  -56.9000 29

#__ type_ start__ end____ width___ exp.time_
 14 omega  -43.00  -21.25   0.7500   34.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  134.6000  123.1000 29

#__ type_ start__ end____ width___ exp.time_
 15 omega  -90.00  -36.00   0.7500   34.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000  134.6000  123.1000 72

#__ type_ start__ end____ width___ exp.time_
 16 omega  -90.00  -36.00   0.7500   34.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000  134.6000  -56.9000 72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω and π scans'
_diffrn_orient_matrix_UB_11      0.0337514000
_diffrn_orient_matrix_UB_12      -0.0953209000
_diffrn_orient_matrix_UB_13      0.0329208000
_diffrn_orient_matrix_UB_21      0.1000157000
_diffrn_orient_matrix_UB_22      0.0036798000
_diffrn_orient_matrix_UB_23      -0.0011868000
_diffrn_orient_matrix_UB_31      -0.0153669000
_diffrn_orient_matrix_UB_32      0.0023362000
_diffrn_orient_matrix_UB_33      0.0755798000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                430
_reflns_number_total             575
_reflns_odcompleteness_completeness 27.40
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.16
_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       
;
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)'
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.10(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         575
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0571
_refine_ls_restrained_S_all      1.096
_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)+(0.0770P)²+0.2860P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1414
_refine_ls_wR_factor_ref         0.1608
_refine_special_details          ?
_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(C10) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C2) \\sim
Ueq, Uanis(C11) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(N3)
\\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(O1) \\sim Ueq,
Uanis(C12) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(N1) \\sim Ueq: with sigma of
0.006 and sigma for terminal atoms of 0.003
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 Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
3.d Idealised tetrahedral OH refined as rotating group:
 O1(H1A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O1 O 0.0455(6) 0.2477(13) 0.1593(5) 0.0363(16) Uani 1 1 d . U . . .
H1A H -0.0658 0.3089 0.1750 0.054 Uiso 1 1 calc GR U . . .
C12 C 0.0569(9) 0.251(2) 0.0064(9) 0.040(3) Uani 1 1 d . U . . .
H12A H 0.0902 0.3590 -0.0663 0.048 Uiso 1 1 calc R . . . .
H12B H -0.0720 0.2530 -0.0216 0.048 Uiso 1 1 calc R . . . .
C13 C 0.2134(11) 0.090(2) -0.0010(10) 0.057(2) Uani 1 1 d . U . . .
H13A H 0.1794 -0.0162 0.0710 0.085 Uiso 1 1 calc GR U . . .
H13B H 0.3408 0.0897 0.0255 0.085 Uiso 1 1 calc GR U . . .
H13C H 0.2216 0.0909 -0.1044 0.085 Uiso 1 1 calc GR U . . .
N1 N 0.3493(7) 0.3569(15) 0.2093(7) 0.035(3) Uani 1 1 d . U . . .
H1 H 0.2583 0.3113 0.2033 0.043 Uiso 1 1 calc R U . . .
N3 N 0.6505(6) 0.3988(15) 0.1895(7) 0.036(3) Uani 1 1 d . U . . .
C2 C 0.5404(8) 0.3162(19) 0.1627(8) 0.036(3) Uani 1 1 d . U . . .
H2 H 0.5915 0.2341 0.1143 0.044 Uiso 1 1 calc R U . . .
C4 C 0.5413(8) 0.6379(19) 0.3057(8) 0.033(3) Uani 1 1 d . U . . .
H4 H 0.6674 0.6554 0.2986 0.039 Uiso 1 1 calc R U . . .
C5 C 0.3808(8) 0.737(2) 0.3651(8) 0.035(3) Uani 1 1 d . U . . .
C6 C 0.1848(8) 0.7138(19) 0.3779(8) 0.033(3) Uani 1 1 d . U . . .
C7 C 0.1626(8) 0.5819(18) 0.3311(7) 0.029(3) Uani 1 1 d . U . . .
H7 H 0.0386 0.5593 0.3421 0.035 Uiso 1 1 calc R U . . .
C8 C 0.3263(8) 0.4856(18) 0.2685(7) 0.029(3) Uani 1 1 d . U . . .
C9 C 0.5166(8) 0.5108(18) 0.2558(7) 0.028(3) Uani 1 1 d . U . . .
C10 C 0.4037(9) 0.881(2) 0.4126(9) 0.0460(19) Uani 1 1 d . U . . .
H10A H 0.3132 0.9944 0.3544 0.069 Uiso 1 1 calc GR U . . .
H10B H 0.5395 0.8880 0.3921 0.069 Uiso 1 1 calc GR U . . .
H10C H 0.3731 0.8509 0.5216 0.069 Uiso 1 1 calc GR U . . .
C11 C 0.0098(9) 0.818(2) 0.4417(9) 0.0405(19) Uani 1 1 d . U . . .
H11A H -0.0238 0.9419 0.3729 0.061 Uiso 1 1 calc GR U . . .
H11B H 0.0416 0.8074 0.5418 0.061 Uiso 1 1 calc GR U . . .
H11C H -0.1026 0.7717 0.4521 0.061 Uiso 1 1 calc GR U . . .

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
O1 0.0344(17) 0.037(4) 0.037(2) -0.015(2) -0.0001(13) -0.009(2)
C12 0.042(3) 0.039(8) 0.041(3) -0.021(5) 0.000(2) -0.007(4)
C13 0.060(3) 0.056(4) 0.049(3) -0.023(3) 0.005(2) -0.008(3)
N1 0.034(2) 0.039(8) 0.037(3) -0.017(4) -0.0009(19) -0.012(4)
N3 0.032(2) 0.036(8) 0.040(3) -0.016(4) 0.003(2) -0.010(4)
C2 0.040(3) 0.035(8) 0.040(3) -0.021(4) 0.004(2) -0.012(4)
C4 0.028(3) 0.036(8) 0.030(3) -0.005(4) 0.000(2) -0.014(4)
C5 0.036(3) 0.039(8) 0.034(3) -0.015(4) -0.002(2) -0.014(4)
C6 0.034(3) 0.037(8) 0.024(3) -0.007(4) 0.002(2) -0.012(4)
C7 0.026(2) 0.031(8) 0.027(3) -0.008(4) -0.001(2) -0.006(4)
C8 0.030(3) 0.029(8) 0.024(3) -0.007(4) -0.001(2) -0.008(4)
C9 0.027(2) 0.027(8) 0.024(3) -0.007(4) 0.000(2) -0.005(4)
C10 0.046(2) 0.047(4) 0.046(3) -0.017(3) -0.0040(18) -0.014(3)
C11 0.039(2) 0.040(4) 0.040(2) -0.014(3) 0.0020(17) -0.010(3)

_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
O1 H1A 0.8200 . ?
O1 C12 1.414(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.479(18) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
N1 H1 0.8600 . ?
N1 C2 1.329(6) . ?
N1 C8 1.365(12) . ?
N3 C2 1.296(9) . ?
N3 C9 1.382(11) . ?
C2 H2 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.373(11) . ?
C4 C9 1.394(12) . ?
C5 C6 1.430(6) . ?
C5 C10 1.505(14) . ?
C6 C7 1.406(13) . ?
C6 C11 1.473(11) . ?
C7 H7 0.9300 . ?
C7 C8 1.388(10) . ?
C8 C9 1.396(6) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

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
C12 O1 H1A 109.5 . . ?
O1 C12 H12A 109.9 . . ?
O1 C12 H12B 109.9 . . ?
O1 C12 C13 108.9(10) . . ?
H12A C12 H12B 108.3 . . ?
C13 C12 H12A 109.9 . . ?
C13 C12 H12B 109.9 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C2 N1 H1 126.9 . . ?
C2 N1 C8 106.3(6) . . ?
C8 N1 H1 126.9 . . ?
C2 N3 C9 103.5(5) . . ?
N1 C2 H2 122.3 . . ?
N3 C2 N1 115.3(8) . . ?
N3 C2 H2 122.3 . . ?
C5 C4 H4 119.8 . . ?
C5 C4 C9 120.5(5) . . ?
C9 C4 H4 119.8 . . ?
C4 C5 C6 121.3(9) . . ?
C4 C5 C10 120.9(5) . . ?
C6 C5 C10 117.7(7) . . ?
C5 C6 C11 122.6(8) . . ?
C7 C6 C5 117.7(7) . . ?
C7 C6 C11 119.6(5) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 C6 119.9(5) . . ?
C8 C7 H7 120.1 . . ?
N1 C8 C7 133.1(5) . . ?
N1 C8 C9 105.2(6) . . ?
C7 C8 C9 121.7(8) . . ?
N3 C9 C4 131.5(4) . . ?
N3 C9 C8 109.6(7) . . ?
C4 C9 C8 118.9(7) . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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
N1 C8 C9 N3 0.2(11) . . . . ?
N1 C8 C9 C4 179.2(8) . . . . ?
C2 N1 C8 C7 178.6(11) . . . . ?
C2 N1 C8 C9 -1.5(11) . . . . ?
C2 N3 C9 C4 -177.6(10) . . . . ?
C2 N3 C9 C8 1.2(10) . . . . ?
C4 C5 C6 C7 1.6(15) . . . . ?
C4 C5 C6 C11 179.7(10) . . . . ?
C5 C4 C9 N3 178.3(10) . . . . ?
C5 C4 C9 C8 -0.5(14) . . . . ?
C5 C6 C7 C8 -2.9(14) . . . . ?
C6 C7 C8 N1 -177.5(10) . . . . ?
C6 C7 C8 C9 2.6(15) . . . . ?
C7 C8 C9 N3 -179.9(9) . . . . ?
C7 C8 C9 C4 -0.9(14) . . . . ?
C8 N1 C2 N3 2.5(12) . . . . ?
C9 N3 C2 N1 -2.3(11) . . . . ?
C9 C4 C5 C6 0.0(16) . . . . ?
C9 C4 C5 C10 -177.2(9) . . . . ?
C10 C5 C6 C7 179.0(8) . . . . ?
C10 C5 C6 C11 -2.9(15) . . . . ?
C11 C6 C7 C8 178.9(9) . . . . ?

_shelx_res_file                  
;
    wz-76.res created by SHELXL-2014/7

TITL WZ-76 in P-1 #2
REM reset to P-1 #2
CELL 0.71073 7.004787 8.452822 9.383448 66.4926 81.8399 71.7051
ZERR 2 0.000661 0.003054 0.001186 0.0222 0.0091 0.0179
LATT 1
SFAC C H N O
UNIT 22 32 4 2
ISOR 0.006 0.003 H11c H10a H10c C10 H11b C9 H11a C5 C2 H2 H10b C11 H13b C7 =
 H13A H4 C8 H13C N3 C6 H1 C4 H1A O1 C12 H7 C13 N1

L.S. 44
PLAN  5
BOND
MORE -1
CONF
BOND $H
fmap 2
acta 52
OMIT 4 4 2
OMIT 3 3 1
OMIT 5 5 4
OMIT -3 -1 1
OMIT 5 3 9
OMIT 3 4 4
OMIT 0 2 6
OMIT 7 5 3
OMIT 3 6 9
OMIT -3 -1 3
OMIT -3 -2 2
OMIT 0 3 4
OMIT -2 2 3
REM <olex2.extras>
REM <HklSrc "%.\\WZ-76.hkl">
REM </olex2.extras>

WGHT    0.077000    0.286000
EXTI    0.104136
FVAR      13.00130
O1    4    0.045479    0.247689    0.159279    11.00000    0.03440    0.03743 =
         0.03698   -0.01479   -0.00012   -0.00920
AFIX 147
H1A   2   -0.065841    0.308865    0.175030    11.00000   -1.50000
AFIX   0
C12   1    0.056864    0.251358    0.006420    11.00000    0.04210    0.03865 =
         0.04053   -0.02095    0.00005   -0.00701
AFIX  23
H12A  2    0.090176    0.359001   -0.066324    11.00000   -1.20000
H12B  2   -0.072030    0.253050   -0.021613    11.00000   -1.20000
AFIX   0
C13   1    0.213392    0.089769   -0.001003    11.00000    0.06014    0.05631 =
         0.04940   -0.02318    0.00545   -0.00836
AFIX 137
H13A  2    0.179354   -0.016214    0.071036    11.00000   -1.50000
H13B  2    0.340822    0.089746    0.025515    11.00000   -1.50000
H13C  2    0.221617    0.090871   -0.104378    11.00000   -1.50000
AFIX   0

N1    3    0.349278    0.356900    0.209278    11.00000    0.03412    0.03917 =
         0.03700   -0.01690   -0.00087   -0.01204
AFIX  43
H1    2    0.258271    0.311310    0.203310    11.00000   -1.20000
AFIX   0
N3    3    0.650546    0.398758    0.189538    11.00000    0.03244    0.03586 =
         0.03998   -0.01619    0.00333   -0.00954
C2    1    0.540367    0.316168    0.162719    11.00000    0.04020    0.03470 =
         0.04025   -0.02074    0.00413   -0.01215
AFIX  43
H2    2    0.591472    0.234140    0.114279    11.00000   -1.20000
AFIX   0
C4    1    0.541284    0.637856    0.305677    11.00000    0.02802    0.03595 =
         0.02983   -0.00502   -0.00002   -0.01386
AFIX  43
H4    2    0.667424    0.655406    0.298596    11.00000   -1.20000
AFIX   0
C5    1    0.380787    0.737280    0.365137    11.00000    0.03593    0.03919 =
         0.03352   -0.01549   -0.00194   -0.01355
C6    1    0.184777    0.713822    0.377878    11.00000    0.03380    0.03719 =
         0.02449   -0.00729    0.00151   -0.01222
C7    1    0.162631    0.581910    0.331114    11.00000    0.02551    0.03094 =
         0.02708   -0.00845   -0.00106   -0.00636
AFIX  43
H7    2    0.038625    0.559273    0.342131    11.00000   -1.20000
AFIX   0
C8    1    0.326259    0.485587    0.268485    11.00000    0.03020    0.02906 =
         0.02433   -0.00740   -0.00068   -0.00766
C9    1    0.516556    0.510758    0.255827    11.00000    0.02670    0.02745 =
         0.02383   -0.00674    0.00043   -0.00548
C10   1    0.403732    0.880613    0.412627    11.00000    0.04574    0.04702 =
         0.04604   -0.01667   -0.00397   -0.01413
AFIX 137
H10A  2    0.313225    0.994383    0.354418    11.00000   -1.50000
H10B  2    0.539543    0.887984    0.392143    11.00000   -1.50000
H10C  2    0.373063    0.850890    0.521609    11.00000   -1.50000
AFIX   0
C11   1    0.009773    0.817734    0.441718    11.00000    0.03891    0.04003 =
         0.04016   -0.01442    0.00196   -0.00994
AFIX 137
H11A  2   -0.023782    0.941908    0.372867    11.00000   -1.50000
H11B  2    0.041635    0.807381    0.541830    11.00000   -1.50000
H11C  2   -0.102624    0.771658    0.452078    11.00000   -1.50000
AFIX   0
HKLF 4

REM  WZ-76 in P-1 #2
REM R1 =  0.0571 for     430 Fo > 4sig(Fo)  and  0.0833 for all     575 data
REM    132 parameters refined using     84 restraints

END

WGHT      0.0771      0.2861

REM Highest difference peak  0.163,  deepest hole -0.167,  1-sigma level  0.034
Q1    1   0.2776  0.4234  0.4826  11.00000  0.05    0.16
Q2    1   0.2609  0.4697  0.4651  11.00000  0.05    0.16
Q3    1   0.1109  1.0261  0.2433  11.00000  0.05    0.13
Q4    1   0.1391  0.9696  0.2625  11.00000  0.05    0.13
Q5    1   0.0849  0.0747  0.2202  11.00000  0.05    0.12
;
_shelx_res_checksum              15141
_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 1404125105.96
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_dMBzIm_EtOH_2_17GPa
_database_code_depnum_ccdc_archive 'CCDC 1451565'
_audit_update_record             
;
2016-03-29 deposited with the CCDC.
2016-04-01 downloaded from the CCDC.
;
_audit_creation_date             2016-03-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            '5,6-dimethylbenzimidazole ethanol solvate'
_chemical_name_systematic        '5,6-dimethylbenzimidazole ethanol solvate'
_chemical_formula_moiety         'C2 H6 O, C9 H10 N2'
_chemical_formula_sum            'C11 H16 N2 O'
_chemical_formula_weight         192.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H14 N2 O1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 0.0009 '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 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0056 0.0036 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.926(3)
_cell_length_b                   8.343(4)
_cell_length_c                   9.223(4)
_cell_angle_alpha                66.57(5)
_cell_angle_beta                 81.99(4)
_cell_angle_gamma                72.07(5)
_cell_volume                     465.2(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1316
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.9710
_cell_measurement_theta_min      3.5870
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_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_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_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
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_exptl_special_details           
;
 Data were collected at room temperature and pressure of 2.17(2) GPa
 (2170000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique.
 Pressure was determined by monitoring the shift of the ruby
 R1-fluorescence line.
;
_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_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      
;
#__ type_ start__ end____ width___ exp.time_
  1 phi    -35.00   19.75   0.7500   35.0000
omega____ theta____ kappa____ phi______ frames
   0.0000  -30.0000    0.0000     -     73

#__ type_ start__ end____ width___ exp.time_
  2 phi    140.00  200.00   0.7500   35.0000
omega____ theta____ kappa____ phi______ frames
   0.0000  -30.0000    0.0000     -     80

#__ type_ start__ end____ width___ exp.time_
  3 phi    160.00  217.00   0.7500   35.0000
omega____ theta____ kappa____ phi______ frames
   0.0000   30.0000    0.0000     -     76

#__ type_ start__ end____ width___ exp.time_
  4 phi    -20.00   34.75   0.7500   35.0000
omega____ theta____ kappa____ phi______ frames
   0.0000   30.0000    0.0000     -     73

#__ type_ start__ end____ width___ exp.time_
  5 omega  -16.00   32.00   0.7500   35.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   39.4600  -12.9000 64

#__ type_ start__ end____ width___ exp.time_
  6 omega  -16.00   32.00   0.7500   35.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   39.4600  167.1000 64

#__ type_ start__ end____ width___ exp.time_
  7 omega  -50.00   10.00   0.7500   35.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000   39.4600  167.1000 80

#__ type_ start__ end____ width___ exp.time_
  8 omega  -50.00   10.00   0.7500   35.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000   39.4600  -12.9000 80

#__ type_ start__ end____ width___ exp.time_
  9 omega  -64.00   -8.50   0.7500   35.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000   81.4000  -28.9000 74

#__ type_ start__ end____ width___ exp.time_
 10 omega  -64.00   -8.50   0.7500   35.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000   81.4000  151.1000 74

#__ type_ start__ end____ width___ exp.time_
 11 omega  -12.00   15.00   0.7500   35.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   81.4000  151.1000 36

#__ type_ start__ end____ width___ exp.time_
 12 omega  -12.00   15.00   0.7500   35.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   81.4000  -28.9000 36

#__ type_ start__ end____ width___ exp.time_
 13 omega  -43.00  -21.25   0.7500   35.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  134.6000  -56.9000 29

#__ type_ start__ end____ width___ exp.time_
 14 omega  -43.00  -21.25   0.7500   35.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  134.6000  123.1000 29

#__ type_ start__ end____ width___ exp.time_
 15 omega  -90.00  -36.00   0.7500   35.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000  134.6000  123.1000 72

#__ type_ start__ end____ width___ exp.time_
 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       'ω and π 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_source                   'Enhance (Ag) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                611
_reflns_number_total             1350
_reflns_odcompleteness_completeness 24.47
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.07
_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       
;
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)'
_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+0.001xFc²λ³/sin(2θ)]^-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_R_factor_all          0.2012
_refine_ls_R_factor_gt           0.1112
_refine_ls_restrained_S_all      1.059
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2820
_refine_ls_wR_factor_ref         0.3637
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O1 O 0.0449(5) 0.2444(11) 0.1603(4) 0.051(3) Uani 1 1 d . U . . .
H1A H -0.0738 0.2873 0.1816 0.076 Uiso 1 1 calc GR U . . .
C12 C 0.0597(8) 0.2478(17) 0.0049(7) 0.044(3) Uani 1 1 d . U . . .
H12A H 0.0975 0.3556 -0.0675 0.053 Uiso 1 1 calc R . . . .
H12B H -0.0710 0.2532 -0.0260 0.053 Uiso 1 1 calc R . . . .
C13 C 0.2135(9) 0.0833(19) -0.0044(9) 0.058(4) Uani 1 1 d . U . . .
H13A H 0.1746 -0.0231 0.0658 0.087 Uiso 1 1 calc GR U . . .
H13B H 0.3430 0.0786 0.0256 0.087 Uiso 1 1 calc GR U . . .
H13C H 0.2227 0.0878 -0.1107 0.087 Uiso 1 1 calc GR U . . .
N1 N 0.3495(6) 0.3552(13) 0.2085(6) 0.042(3) Uani 1 1 d . U . . .
H1 H 0.2564 0.3107 0.2007 0.050 Uiso 1 1 calc R . . . .
N3 N 0.6546(5) 0.3984(12) 0.1875(5) 0.041(3) Uani 1 1 d . U . . .
C2 C 0.5434(7) 0.3133(15) 0.1606(7) 0.046(3) Uani 1 1 d . U . . .
H2 H 0.5945 0.2298 0.1119 0.055 Uiso 1 1 calc R U . . .
C8 C 0.3285(4) 0.4793(6) 0.2704(4) 0.033(3) Uani 1 1 d . U . . .
C9 C 0.5176(3) 0.5099(7) 0.2571(4) 0.039(3) Uani 1 1 d G U . . .
C4 C 0.5419(3) 0.6404(7) 0.3053(4) 0.037(3) Uani 1 1 d G U . . .
H4 H 0.6684 0.6609 0.2964 0.044 Uiso 1 1 calc R U . . .
C5 C 0.3771(4) 0.7403(6) 0.3670(4) 0.039(3) Uani 1 1 d G U . . .
C6 C 0.1879(3) 0.7098(7) 0.3804(4) 0.037(3) Uani 1 1 d G U . . .
C7 C 0.1636(3) 0.5792(7) 0.3321(4) 0.032(3) Uani 1 1 d G U . . .
H7 H 0.0371 0.5588 0.3411 0.038 Uiso 1 1 calc R U . . .
C10 C 0.4036(8) 0.8815(16) 0.4144(7) 0.041(4) Uani 1 1 d . U . . .
H10A H 0.3110 0.9965 0.3574 0.061 Uiso 1 1 calc GR U . . .
H10B H 0.5404 0.8899 0.3909 0.061 Uiso 1 1 calc GR U . . .
H10C H 0.3765 0.8499 0.5258 0.061 Uiso 1 1 calc GR U . . .
C11 C 0.0071(7) 0.8158(17) 0.4436(7) 0.043(4) Uani 1 1 d . U . . .
H11A H -0.0210 0.9423 0.3766 0.065 Uiso 1 1 calc GR U . . .
H11B H 0.0337 0.8004 0.5485 0.065 Uiso 1 1 calc GR U . . .
H11C H -0.1078 0.7732 0.4466 0.065 Uiso 1 1 calc GR U . . .

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
O1 0.0373(18) 0.075(10) 0.045(2) -0.031(5) 0.0032(18) -0.012(4)
C12 0.044(2) 0.046(8) 0.047(3) -0.025(4) 0.006(2) -0.012(4)
C13 0.060(3) 0.061(13) 0.049(4) -0.025(6) 0.001(3) -0.007(6)
N1 0.0375(19) 0.050(8) 0.046(2) -0.028(4) 0.0033(17) -0.010(3)
N3 0.035(2) 0.043(8) 0.044(3) -0.019(4) 0.0050(18) -0.007(3)
C2 0.042(2) 0.048(8) 0.047(3) -0.023(4) 0.005(2) -0.008(4)
C8 0.036(2) 0.031(8) 0.029(2) -0.007(4) -0.0014(17) -0.012(3)
C9 0.032(2) 0.044(8) 0.037(3) -0.016(4) 0.0007(18) -0.007(4)
C4 0.030(2) 0.039(8) 0.035(3) -0.010(4) -0.0008(18) -0.006(4)
C5 0.035(2) 0.044(8) 0.037(3) -0.016(4) -0.0043(18) -0.006(4)
C6 0.040(2) 0.041(8) 0.030(2) -0.012(4) 0.0032(17) -0.013(4)
C7 0.030(2) 0.030(8) 0.031(3) -0.009(4) 0.0010(17) -0.008(3)
C10 0.042(3) 0.026(12) 0.049(4) -0.013(6) -0.007(2) -0.003(5)
C11 0.034(2) 0.042(12) 0.043(3) -0.014(6) 0.002(2) 0.001(5)

_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
O1 H1A 0.8200 . ?
O1 C12 1.412(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.482(13) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
N1 H1 0.8600 . ?
N1 C2 1.338(5) . ?
N1 C8 1.332(7) . ?
N3 C2 1.300(8) . ?
N3 C9 1.392(6) . ?
C2 H2 0.9300 . ?
C8 C9 1.3900 . ?
C8 C7 1.3900 . ?
C9 C4 1.3900 . ?
C4 H4 0.9300 . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C5 C10 1.475(9) . ?
C6 C7 1.3900 . ?
C6 C11 1.489(7) . ?
C7 H7 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

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
C12 O1 H1A 109.5 . . ?
O1 C12 H12A 109.6 . . ?
O1 C12 H12B 109.6 . . ?
O1 C12 C13 110.4(8) . . ?
H12A C12 H12B 108.1 . . ?
C13 C12 H12A 109.6 . . ?
C13 C12 H12B 109.6 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C2 N1 H1 126.7 . . ?
C8 N1 H1 126.7 . . ?
C8 N1 C2 106.7(4) . . ?
C2 N3 C9 103.1(3) . . ?
N1 C2 H2 122.6 . . ?
N3 C2 N1 114.7(6) . . ?
N3 C2 H2 122.6 . . ?
N1 C8 C9 106.4(2) . . ?
N1 C8 C7 133.5(2) . . ?
C9 C8 C7 120.0 . . ?
C8 C9 N3 109.1(2) . . ?
C4 C9 N3 130.9(2) . . ?
C4 C9 C8 120.0 . . ?
C9 C4 H4 120.0 . . ?
C9 C4 C5 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 C10 119.5(2) . . ?
C6 C5 C10 120.5(2) . . ?
C5 C6 C11 121.6(3) . . ?
C7 C6 C5 120.0 . . ?
C7 C6 C11 118.4(3) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 C8 120.0 . . ?
C6 C7 H7 120.0 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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
N1 C8 C9 N3 -1.0(5) . . . . ?
N1 C8 C9 C4 177.0(4) . . . . ?
N1 C8 C7 C6 -176.0(5) . . . . ?
N3 C9 C4 C5 177.4(5) . . . . ?
C2 N1 C8 C9 0.2(6) . . . . ?
C2 N1 C8 C7 176.6(5) . . . . ?
C2 N3 C9 C8 1.3(6) . . . . ?
C2 N3 C9 C4 -176.3(5) . . . . ?
C8 N1 C2 N3 0.7(9) . . . . ?
C8 C9 C4 C5 0.0 . . . . ?
C9 N3 C2 N1 -1.3(8) . . . . ?
C9 C8 C7 C6 0.0 . . . . ?
C9 C4 C5 C6 0.0 . . . . ?
C9 C4 C5 C10 -178.6(5) . . . . ?
C4 C5 C6 C7 0.0 . . . . ?
C4 C5 C6 C11 -179.1(5) . . . . ?
C5 C6 C7 C8 0.0 . . . . ?
C7 C8 C9 N3 -177.9(4) . . . . ?
C7 C8 C9 C4 0.0 . . . . ?
C10 C5 C6 C7 178.6(5) . . . . ?
C10 C5 C6 C11 -0.5(7) . . . . ?
C11 C6 C7 C8 179.1(5) . . . . ?

_shelx_res_file                  
;
    37.res created by SHELXL-2014/7

TITL 37 in P-1 #2
REM reset to P-1 #2
CELL 0.56087 6.92632 8.342815 9.223461 66.5653 81.9875 72.0728
ZERR 2 0.003047 0.004431 0.004082 0.0475 0.038 0.0491
LATT 1
SFAC C H N O
UNIT 22 32 4 2
ISOR 0.007 0.012 C2 H13c H13b H2 C13 H13a N3 C12 N1 C6 H10b H10c H11c H1a =
 C10 H7 C7 O1 C11 H11B C9 H4 H11A C8 H10A C4 C5

L.S. 44
PLAN  5
BOND
MORE -1
CONF
BOND $H
fmap 2
acta
OMIT 4 4 2
OMIT 3 5 5
OMIT 2 4 4
OMIT -12 -3 1
OMIT 3 3 1
OMIT 3 4 3
OMIT 2 5 6
OMIT 4 8 15
OMIT 2 6 8
OMIT 6 7 7
OMIT 10 1 0
OMIT 4 7 9
OMIT 6 6 4
OMIT -1 4 6
OMIT -3 2 6
OMIT 1 4 5
OMIT 1 5 7
OMIT -3 4 7
OMIT 6 6 5
OMIT -4 4 13
OMIT 7 8 10
REM <olex2.extras>
REM <HklSrc "%.\\37.hkl">
REM </olex2.extras>

WGHT    0.200000
EXTI    0.386850
FVAR       7.27887
O1    4    0.044903    0.244438    0.160343    11.00000    0.03729    0.07515 =
         0.04460   -0.03093    0.00319   -0.01229
AFIX 147
H1A   2   -0.073824    0.287292    0.181619    11.00000   -1.50000
AFIX   0
C12   1    0.059741    0.247841    0.004943    11.00000    0.04386    0.04577 =
         0.04714   -0.02495    0.00591   -0.01171
AFIX  23
H12A  2    0.097499    0.355567   -0.067497    11.00000   -1.20000
H12B  2   -0.071039    0.253243   -0.026027    11.00000   -1.20000
AFIX   0
C13   1    0.213539    0.083300   -0.004428    11.00000    0.05977    0.06136 =
         0.04887   -0.02501    0.00087   -0.00690
AFIX 137
H13A  2    0.174554   -0.023078    0.065791    11.00000   -1.50000
H13B  2    0.343043    0.078603    0.025569    11.00000   -1.50000
H13C  2    0.222672    0.087761   -0.110716    11.00000   -1.50000
AFIX   0

N1    3    0.349453    0.355246    0.208457    11.00000    0.03751    0.04957 =
         0.04589   -0.02801    0.00327   -0.01025
AFIX  43
H1    2    0.256399    0.310748    0.200705    11.00000   -1.20000
AFIX   0
N3    3    0.654610    0.398445    0.187464    11.00000    0.03541    0.04300 =
         0.04372   -0.01909    0.00496   -0.00718
C2    1    0.543351    0.313302    0.160590    11.00000    0.04175    0.04793 =
         0.04749   -0.02313    0.00457   -0.00767
AFIX  43
H2    2    0.594542    0.229801    0.111916    11.00000   -1.20000
AFIX  66
C8    1    0.328456    0.479279    0.270447    11.00000    0.03571    0.03123 =
         0.02932   -0.00742   -0.00141   -0.01199
C9    1    0.517585    0.509869    0.257066    11.00000    0.03219    0.04439 =
         0.03709   -0.01616    0.00072   -0.00728
C4    1    0.541897    0.640400    0.305346    11.00000    0.03049    0.03902 =
         0.03495   -0.01015   -0.00084   -0.00632
AFIX  43
H4    2    0.668438    0.660867    0.296393    11.00000   -1.20000
AFIX  65
C5    1    0.377080    0.740342    0.367006    11.00000    0.03520    0.04400 =
         0.03705   -0.01636   -0.00432   -0.00642
C6    1    0.187949    0.709753    0.380388    11.00000    0.03960    0.04083 =
         0.03022   -0.01211    0.00323   -0.01293
C7    1    0.163634    0.579223    0.332109    11.00000    0.02959    0.03035 =
         0.03115   -0.00854    0.00099   -0.00765
AFIX  43
H7    2    0.037092    0.558757    0.341062    11.00000   -1.20000
AFIX   0
C10   1    0.403554    0.881482    0.414398    11.00000    0.04188    0.02620 =
         0.04916   -0.01253   -0.00735   -0.00264
AFIX 137
H10A  2    0.311047    0.996461    0.357376    11.00000   -1.50000
H10B  2    0.540367    0.889919    0.390870    11.00000   -1.50000
H10C  2    0.376480    0.849920    0.525790    11.00000   -1.50000
AFIX   0
C11   1    0.007141    0.815810    0.443636    11.00000    0.03365    0.04225 =
         0.04301   -0.01445    0.00237    0.00143
AFIX 137
H11A  2   -0.021014    0.942272    0.376583    11.00000   -1.50000
H11B  2    0.033662    0.800358    0.548499    11.00000   -1.50000
H11C  2   -0.107817    0.773192    0.446612    11.00000   -1.50000
AFIX   0
HKLF 4

REM  37 in P-1 #2
REM R1 =  0.1112 for     611 Fo > 4sig(Fo)  and  0.2012 for all    1350 data
REM    120 parameters refined using     84 restraints

END

WGHT      0.2000      0.0000

REM Highest difference peak  0.313,  deepest hole -0.320,  1-sigma level  0.058
Q1    1   0.1743  0.6528  0.4004  11.00000  0.05    0.30
Q2    1   0.1398  0.7503  0.3712  11.00000  0.05    0.30
Q3    1   0.4195  0.6980  0.3749  11.00000  0.05    0.29
Q4    1   0.4331  0.6530  0.3877  11.00000  0.05    0.28
Q5    1   0.2827  0.5728  0.2441  11.00000  0.05    0.28
;
_shelx_res_checksum              39089
_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_dMBzIm_MeOH_0_92GPa
_database_code_depnum_ccdc_archive 'CCDC 1451566'
_audit_update_record             
;
2016-03-29 deposited with the CCDC.
2016-04-01 downloaded from the CCDC.
;
_audit_creation_date             2016-03-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            '5,6-dimethylbenzimidazole methanol solvate'
_chemical_name_systematic        '5,6-dimethylbenzimidazole methanol solvate'
_chemical_formula_moiety         'C10 H14 N2 O'
_chemical_formula_sum            'C10 H14 N2 O'
_chemical_formula_weight         178.23
_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 0.0033 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'
O O 0.0106 0.0060 '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 21/c'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.977(7)
_cell_length_b                   7.1746(3)
_cell_length_c                   12.7576(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.545(13)
_cell_angle_gamma                90
_cell_volume                     911.4(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1371
_cell_measurement_temperature    296
_cell_measurement_theta_max      24.9690
_cell_measurement_theta_min      3.2470
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.03953
_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_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             384
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.35
_exptl_special_details           
;
 Data were collected at room temperature and pressure of 0.92(2) GPa
 (920000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique.
 Pressure was determined by monitoring the shift of the ruby
 R1-fluorescence line.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_Laue_measured_fraction_full 0.301
_diffrn_reflns_Laue_measured_fraction_max 0.276
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6238
_diffrn_reflns_point_group_measured_fraction_full 0.301
_diffrn_reflns_point_group_measured_fraction_max 0.276
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.153
_diffrn_reflns_theta_min         3.200
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      296
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1544
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.301
_diffrn_measured_fraction_theta_max 0.276
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 phi    -35.00   19.60   0.7000   32.0000
omega____ theta____ kappa____ phi______ frames
   0.0000  -30.0000    0.0000     -     78

#__ type_ start__ end____ width___ exp.time_
  2 phi    140.00  199.50   0.7000   32.0000
omega____ theta____ kappa____ phi______ frames
   0.0000  -30.0000    0.0000     -     85

#__ type_ start__ end____ width___ exp.time_
  3 phi    160.00  216.70   0.7000   32.0000
omega____ theta____ kappa____ phi______ frames
   0.0000   30.0000    0.0000     -     81

#__ type_ start__ end____ width___ exp.time_
  4 phi    -20.00   34.60   0.7000   32.0000
omega____ theta____ kappa____ phi______ frames
   0.0000   30.0000    0.0000     -     78

#__ type_ start__ end____ width___ exp.time_
  5 omega  -24.00   23.60   0.7000   32.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   39.4600  -12.9000 68

#__ type_ start__ end____ width___ exp.time_
  6 omega  -24.00   23.60   0.7000   32.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   39.4600  167.1000 68

#__ type_ start__ end____ width___ exp.time_
  7 omega  -50.00    9.50   0.7000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000   39.4600  167.1000 85

#__ type_ start__ end____ width___ exp.time_
  8 omega  -50.00    9.50   0.7000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000   39.4600  -12.9000 85

#__ type_ start__ end____ width___ exp.time_
  9 omega  -64.00   -8.00   0.7000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000   81.4000  -28.9000 80

#__ type_ start__ end____ width___ exp.time_
 10 omega  -64.00   -8.00   0.7000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000   81.4000  151.1000 80

#__ type_ start__ end____ width___ exp.time_
 11 omega  -19.00    7.60   0.7000   32.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   81.4000  151.1000 38

#__ type_ start__ end____ width___ exp.time_
 12 omega  -19.00    7.60   0.7000   32.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   81.4000  -28.9000 38

#__ type_ start__ end____ width___ exp.time_
 13 omega  -43.00  -21.30   0.7000   32.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  134.6000  -56.9000 31

#__ type_ start__ end____ width___ exp.time_
 14 omega  -43.00  -21.30   0.7000   32.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  134.6000  123.1000 31

#__ type_ start__ end____ width___ exp.time_
 15 omega  -90.00  -36.10   0.7000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000  134.6000  123.1000 77

#__ type_ start__ end____ width___ exp.time_
 16 omega  -90.00  -36.10   0.7000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000  134.6000  -56.9000 77
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω and π scans'
_diffrn_orient_matrix_UB_11      0.0713285000
_diffrn_orient_matrix_UB_12      0.0016593000
_diffrn_orient_matrix_UB_13      0.0024405000
_diffrn_orient_matrix_UB_21      -0.0010094000
_diffrn_orient_matrix_UB_22      0.0979518000
_diffrn_orient_matrix_UB_23      0.0070770000
_diffrn_orient_matrix_UB_31      0.0014847000
_diffrn_orient_matrix_UB_32      -0.0125941000
_diffrn_orient_matrix_UB_33      0.0551598000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                349
_reflns_number_total             617
_reflns_odcompleteness_completeness 27.38
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.26
_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       
;
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)'
_refine_diff_density_max         0.119
_refine_diff_density_min         -0.115
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     123
_refine_ls_number_reflns         617
_refine_ls_number_restraints     108
_refine_ls_R_factor_all          0.1064
_refine_ls_R_factor_gt           0.0501
_refine_ls_restrained_S_all      0.977
_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)+(0.0907P)²+0.2616P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1296
_refine_ls_wR_factor_ref         0.1788
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.01 and sigma
for terminal atoms of 0.01
4. Others
 Sof(H1B)=Sof(H3)=1-FVAR(1)
 Sof(H1A)=Sof(H1)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), C2(H2), C4(H4), C7(H7)
5.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
5.c Idealised tetrahedral OH refined as rotating group:
 O1(H1A), O1(H1B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O1 O 0.5859(9) 0.8590(4) 0.0899(2) 0.065(3) Uani 1 1 d . U . . .
H1A H 0.6044 0.9643 0.0703 0.098 Uiso 0.13(5) 1 calc GR . P . .
H1B H 0.6216 0.7560 0.0921 0.098 Uiso 0.87(5) 1 calc GR . P . .
N1 N 0.6876(15) 0.5119(7) 0.0978(4) 0.051(3) Uani 1 1 d . U . . .
H1 H 0.6578 0.6239 0.1024 0.061 Uiso 0.13(5) 1 calc R . P . .
N3 N 0.6917(15) 0.2091(7) 0.0737(4) 0.048(3) Uani 1 1 d . U . . .
H3 H 0.6622 0.0980 0.0619 0.057 Uiso 0.87(5) 1 calc R . P . .
C2 C 0.6161(14) 0.3637(5) 0.0780(3) 0.050(3) Uani 1 1 d . U . . .
H2 H 0.5229 0.3642 0.0679 0.060 Uiso 1 1 calc R . . . .
C4 C 0.948(3) 0.1634(7) 0.0990(4) 0.046(3) Uani 1 1 d . U . . .
H4 H 0.9502 0.0351 0.0890 0.055 Uiso 1 1 calc R . . . .
C5 C 1.058(2) 0.2593(7) 0.1204(4) 0.046(3) Uani 1 1 d . U . . .
C6 C 1.056(2) 0.4548(7) 0.1386(4) 0.044(3) Uani 1 1 d . U . . .
C7 C 0.934(2) 0.5508(7) 0.1316(4) 0.042(3) Uani 1 1 d . U . . .
H7 H 0.9305 0.6791 0.1417 0.051 Uiso 1 1 calc R . . . .
C8 C 0.824(3) 0.4553(8) 0.1106(5) 0.044(3) Uani 1 1 d . U . . .
C9 C 0.827(3) 0.2599(8) 0.0918(5) 0.044(3) Uani 1 1 d . U . . .
C10 C 1.198(2) 0.1587(8) 0.1260(4) 0.064(3) Uani 1 1 d . U . . .
H10A H 1.2390 0.1695 0.1957 0.096 Uiso 1 1 calc GR . . . .
H10B H 1.2546 0.2157 0.0770 0.096 Uiso 1 1 calc GR . . . .
H10C H 1.1856 0.0294 0.1086 0.096 Uiso 1 1 calc GR . . . .
C11 C 1.1893(19) 0.5545(7) 0.1630(4) 0.059(3) Uani 1 1 d . U . . .
H11A H 1.1736 0.6860 0.1691 0.088 Uiso 1 1 calc GR . . . .
H11B H 1.2479 0.5321 0.1075 0.088 Uiso 1 1 calc GR . . . .
H11C H 1.2302 0.5083 0.2280 0.088 Uiso 1 1 calc GR . . . .
C12 C 0.4914(15) 0.8701(6) 0.1673(4) 0.070(4) Uani 1 1 d . U . . .
H12A H 0.4394 0.7575 0.1669 0.104 Uiso 1 1 calc GR . . . .
H12B H 0.4330 0.9745 0.1528 0.104 Uiso 1 1 calc GR . . . .
H12C H 0.5376 0.8860 0.2350 0.104 Uiso 1 1 calc GR . . . .

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
O1 0.078(11) 0.0408(15) 0.078(2) 0.0014(14) 0.011(4) 0.003(3)
N1 0.053(8) 0.046(2) 0.051(2) 0.0000(18) -0.011(5) -0.008(4)
N3 0.049(8) 0.043(2) 0.052(2) 0.0026(17) 0.010(5) -0.007(5)
C2 0.050(8) 0.048(2) 0.051(2) 0.0041(17) 0.004(5) 0.001(4)
C4 0.053(7) 0.038(2) 0.047(2) 0.0035(19) 0.013(5) -0.001(5)
C5 0.049(8) 0.051(3) 0.039(2) 0.0042(19) 0.007(5) 0.002(5)
C6 0.045(8) 0.051(3) 0.037(2) 0.0017(18) 0.011(5) -0.005(5)
C7 0.048(7) 0.0361(19) 0.045(2) -0.0009(18) 0.023(5) -0.002(5)
C8 0.050(7) 0.042(3) 0.040(2) 0.005(2) 0.000(7) 0.003(5)
C9 0.050(7) 0.042(3) 0.041(2) 0.005(2) -0.001(6) -0.005(5)
C10 0.056(9) 0.075(3) 0.063(3) 0.006(2) 0.017(6) 0.004(6)
C11 0.053(9) 0.074(3) 0.053(2) -0.001(2) 0.025(5) -0.020(5)
C12 0.075(12) 0.057(2) 0.077(3) -0.007(2) 0.008(5) -0.001(4)

_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
O1 H1A 0.8200 . ?
O1 H1B 0.8200 . ?
O1 C12 1.410(12) . ?
N1 H1 0.8600 . ?
N1 C2 1.297(13) . ?
N1 C8 1.42(3) . ?
N3 H3 0.8600 . ?
N3 C2 1.344(13) . ?
N3 C9 1.40(3) . ?
C2 H2 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.31(3) . ?
C4 C9 1.39(4) . ?
C5 C6 1.422(7) . ?
C5 C10 1.57(3) . ?
C6 C7 1.40(3) . ?
C6 C11 1.53(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.31(4) . ?
C8 C9 1.423(8) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

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
H1A O1 H1B 137.4 . . ?
C12 O1 H1A 109.5 . . ?
C12 O1 H1B 109.5 . . ?
C2 N1 H1 126.3 . . ?
C2 N1 C8 107.4(8) . . ?
C8 N1 H1 126.3 . . ?
C2 N3 H3 125.8 . . ?
C2 N3 C9 108.4(9) . . ?
C9 N3 H3 125.8 . . ?
N1 C2 N3 112.4(13) . . ?
N1 C2 H2 123.8 . . ?
N3 C2 H2 123.8 . . ?
C5 C4 H4 121.1 . . ?
C5 C4 C9 117.7(7) . . ?
C9 C4 H4 121.1 . . ?
C4 C5 C6 122(2) . . ?
C4 C5 C10 120.1(7) . . ?
C6 C5 C10 117.8(18) . . ?
C5 C6 C11 118.5(17) . . ?
C7 C6 C5 119.6(19) . . ?
C7 C6 C11 121.9(6) . . ?
C6 C7 H7 120.9 . . ?
C8 C7 C6 118.2(7) . . ?
C8 C7 H7 120.9 . . ?
N1 C8 C9 107.1(19) . . ?
C7 C8 N1 131.2(8) . . ?
C7 C8 C9 122(2) . . ?
N3 C9 C8 105(2) . . ?
C4 C9 N3 134.7(8) . . ?
C4 C9 C8 121(2) . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
N1 C8 C9 N3 -2.7(7) . . . . ?
N1 C8 C9 C4 -179.7(6) . . . . ?
C2 N1 C8 C7 -179.8(6) . . . . ?
C2 N1 C8 C9 2.5(7) . . . . ?
C2 N3 C9 C4 178.4(6) . . . . ?
C2 N3 C9 C8 1.9(7) . . . . ?
C4 C5 C6 C7 -1.4(7) . . . . ?
C4 C5 C6 C11 180.0(5) . . . . ?
C5 C4 C9 N3 -178.0(7) . . . . ?
C5 C4 C9 C8 -2.0(9) . . . . ?
C5 C6 C7 C8 1.5(7) . . . . ?
C6 C7 C8 N1 -179.4(6) . . . . ?
C6 C7 C8 C9 -2.0(8) . . . . ?
C7 C8 C9 N3 179.3(6) . . . . ?
C7 C8 C9 C4 2.3(9) . . . . ?
C8 N1 C2 N3 -1.3(6) . . . . ?
C9 N3 C2 N1 -0.4(7) . . . . ?
C9 C4 C5 C6 1.6(8) . . . . ?
C9 C4 C5 C10 -178.1(5) . . . . ?
C10 C5 C6 C7 178.3(5) . . . . ?
C10 C5 C6 C11 -0.4(6) . . . . ?
C11 C6 C7 C8 -179.9(5) . . . . ?

_shelx_res_file                  
;
    37b.res created by SHELXL-2014/7

TITL 37b in P21/c #14
REM reset to P21/c #14
CELL 0.71073 9.976687 7.174626 12.757629 90 93.5451 90
ZERR 4 0.006651 0.000338 0.000554 0 0.013 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O
UNIT 40 56 8 4
DELU
ISOR 0.01 0.01

L.S. 44
PLAN  5
BOND
MORE -1
CONF
BOND $H
fmap 2
acta 52
OMIT -1 5 2
OMIT -3 1 10
OMIT -3 0 10
OMIT -2 5 1
OMIT -1 6 3
OMIT 2 6 5
OMIT -3 2 11
OMIT 1 9 2
OMIT 2 6 1
OMIT -1 3 1
OMIT -3 4 7
OMIT 0 6 3
OMIT 0 8 0
OMIT -3 5 4
OMIT 1 6 1
OMIT -3 4 10
OMIT 1 5 2
OMIT -2 0 8
OMIT -1 9 2
REM <olex2.extras>
REM <HklSrc "%.\\37b.hkl">
REM </olex2.extras>

WGHT    0.090700    0.261600
FVAR       6.91487   0.13433
O1    4    0.585945    0.859043    0.089857    11.00000    0.07769    0.04082 =
         0.07788    0.00136    0.01075    0.00255
AFIX 147
H1A   2    0.604373    0.964350    0.070324    21.00000   -1.50000
AFIX 147
H1B   2    0.621560    0.755998    0.092118   -21.00000   -1.50000
AFIX   0
N1    3    0.687563    0.511875    0.097847    11.00000    0.05300    0.04589 =
         0.05105   -0.00001   -0.01129   -0.00804
AFIX  43
H1    2    0.657828    0.623904    0.102421    21.00000   -1.20000
AFIX   0
N3    3    0.691696    0.209143    0.073715    11.00000    0.04943    0.04268 =
         0.05211    0.00262    0.01029   -0.00663
AFIX  43
H3    2    0.662187    0.098026    0.061864   -21.00000   -1.20000
AFIX   0
C2    1    0.616068    0.363675    0.078024    11.00000    0.05025    0.04752 =
         0.05125    0.00414    0.00394    0.00113
AFIX  43
H2    2    0.522948    0.364230    0.067925    11.00000   -1.20000
AFIX   0
C4    1    0.947573    0.163427    0.098996    11.00000    0.05285    0.03797 =
         0.04702    0.00353    0.01278   -0.00127
AFIX  43
H4    2    0.950233    0.035120    0.088970    11.00000   -1.20000
AFIX   0
C5    1    1.057782    0.259280    0.120391    11.00000    0.04906    0.05114 =
         0.03914    0.00421    0.00742    0.00187
C6    1    1.056000    0.454753    0.138601    11.00000    0.04536    0.05144 =
         0.03652    0.00166    0.01092   -0.00451
C7    1    0.933561    0.550788    0.131608    11.00000    0.04751    0.03606 =
         0.04544   -0.00091    0.02313   -0.00192
AFIX  43
H7    2    0.930532    0.679069    0.141656    11.00000   -1.20000
AFIX   0
C8    1    0.823830    0.455314    0.110604    11.00000    0.04950    0.04158 =
         0.04032    0.00549   -0.00050    0.00298
C9    1    0.826936    0.259898    0.091832    11.00000    0.04954    0.04160 =
         0.04080    0.00504   -0.00129   -0.00529
C10   1    1.197866    0.158684    0.125976    11.00000    0.05562    0.07533 =
         0.06264    0.00638    0.01685    0.00417
AFIX 137
H10A  2    1.239025    0.169494    0.195741    11.00000   -1.50000
H10B  2    1.254588    0.215705    0.077008    11.00000   -1.50000
H10C  2    1.185607    0.029367    0.108593    11.00000   -1.50000
AFIX   0
C11   1    1.189281    0.554534    0.163043    11.00000    0.05316    0.07363 =
         0.05265   -0.00142    0.02539   -0.01975
AFIX 137
H11A  2    1.173614    0.686010    0.169059    11.00000   -1.50000
H11B  2    1.247878    0.532105    0.107469    11.00000   -1.50000
H11C  2    1.230234    0.508286    0.227986    11.00000   -1.50000
AFIX   0
C12   1    0.491427    0.870128    0.167342    11.00000    0.07482    0.05710 =
         0.07717   -0.00670    0.00757   -0.00104
AFIX 137
H12A  2    0.439419    0.757524    0.166926    11.00000   -1.50000
H12B  2    0.432954    0.974457    0.152809    11.00000   -1.50000
H12C  2    0.537552    0.885950    0.235049    11.00000   -1.50000
AFIX   0
HKLF 4

REM  37b in P21/c #14
REM R1 =  0.0501 for     349 Fo > 4sig(Fo)  and  0.1064 for all     617 data
REM    123 parameters refined using    108 restraints

END

WGHT      0.0907      0.2617

REM Highest difference peak  0.119,  deepest hole -0.115,  1-sigma level  0.028
Q1    1   0.8500  0.8668  0.1348  11.00000  0.05    0.12
Q2    1   0.7943  0.8549  0.1242  11.00000  0.05    0.12
Q3    1   1.2423 -0.1314  0.1385  11.00000  0.05    0.11
Q4    1   1.1715  0.8474  0.1242  11.00000  0.05    0.10
Q5    1   0.5988  0.9993  0.2206  11.00000  0.05    0.09
;
_shelx_res_checksum              426
_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_dMBzIm_MeOH_1_24GPa
_database_code_depnum_ccdc_archive 'CCDC 1451567'
_audit_update_record             
;
2016-03-29 deposited with the CCDC.
2016-04-01 downloaded from the CCDC.
;
_audit_creation_date             2016-03-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            '5,6-dimethylbenzimidazole methanol solvate'
_chemical_name_systematic        '5,6-dimethylbenzimidazole methanol solvate'
_chemical_formula_moiety         'C10 H14 N2 O'
_chemical_formula_sum            'C10 H14 N2 O'
_chemical_formula_weight         178.23
_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 0.0033 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'
O O 0.0106 0.0060 '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 21/c'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.960(12)
_cell_length_b                   7.1574(10)
_cell_length_c                   12.5790(8)
_cell_angle_alpha                90
_cell_angle_beta                 93.71(2)
_cell_angle_gamma                90
_cell_volume                     894.8(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    632
_cell_measurement_temperature    296
_cell_measurement_theta_max      25.3000
_cell_measurement_theta_min      4.2950
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58603
_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_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.35
_exptl_special_details           
;
 Data were collected at room temperature and pressure of 1.24(2) GPa
 (1240000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique.
 Pressure was determined by monitoring the shift of the ruby
 R1-fluorescence line.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_Laue_measured_fraction_full 0.247
_diffrn_reflns_Laue_measured_fraction_max 0.226
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2381
_diffrn_reflns_point_group_measured_fraction_full 0.247
_diffrn_reflns_point_group_measured_fraction_max 0.226
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.173
_diffrn_reflns_theta_min         4.319
_diffrn_ambient_temperature      296
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2413
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.247
_diffrn_measured_fraction_theta_max 0.226
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 phi    -35.00   19.60   0.7000   33.0000
omega____ theta____ kappa____ phi______ frames
   0.0000  -30.0000    0.0000     -     78

#__ type_ start__ end____ width___ exp.time_
  2 phi    140.00  199.50   0.7000   33.0000
omega____ theta____ kappa____ phi______ frames
   0.0000  -30.0000    0.0000     -     85

#__ type_ start__ end____ width___ exp.time_
  3 phi    160.00  216.70   0.7000   33.0000
omega____ theta____ kappa____ phi______ frames
   0.0000   30.0000    0.0000     -     81

#__ type_ start__ end____ width___ exp.time_
  4 phi    -20.00   34.60   0.7000   33.0000
omega____ theta____ kappa____ phi______ frames
   0.0000   30.0000    0.0000     -     78

#__ type_ start__ end____ width___ exp.time_
  5 omega  -24.00   23.60   0.7000   33.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   39.4600  -12.9000 68

#__ type_ start__ end____ width___ exp.time_
  6 omega  -24.00   23.60   0.7000   33.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   39.4600  167.1000 68

#__ type_ start__ end____ width___ exp.time_
  7 omega  -50.00    8.80   0.7000   33.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000   39.4600  167.1000 84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω and π scans'
_diffrn_orient_matrix_UB_11      -0.0716908000
_diffrn_orient_matrix_UB_12      0.0010033000
_diffrn_orient_matrix_UB_13      -0.0031526000
_diffrn_orient_matrix_UB_21      -0.0003532000
_diffrn_orient_matrix_UB_22      0.0287307000
_diffrn_orient_matrix_UB_23      -0.0538377000
_diffrn_orient_matrix_UB_31      -0.0009815000
_diffrn_orient_matrix_UB_32      -0.0946012000
_diffrn_orient_matrix_UB_33      -0.0164116000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                277
_reflns_number_total             449
_reflns_odcompleteness_completeness 22.99
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.11
_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       
;
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)'
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         449
_refine_ls_number_restraints     74
_refine_ls_R_factor_all          0.1198
_refine_ls_R_factor_gt           0.0644
_refine_ls_restrained_S_all      1.003
_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)+(0.0827P)²+1.3302P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1532
_refine_ls_wR_factor_ref         0.2050
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 H1A-N3_$1
 1.94 with sigma of 0.02
 H1B-N1
 1.94 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C10) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C9) \\sim
Ueq, Uanis(C5) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(O1) \\sim Ueq, Uanis(C12)
\\sim Ueq, Uanis(N3) \\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(C2) \\sim Ueq,
Uanis(C7) \\sim Ueq: with sigma of 0.003 and sigma for terminal atoms of 0.002
4. Others
 Sof(H1B)=Sof(H3)=1-FVAR(1)
 Sof(H1A)=Sof(H1)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), C2(H2), C7(H7), C4(H4)
5.b Fitted hexagon refined as free rotating group:
 C7(C8,C9,C4,C5,C6)
5.c Idealised Me refined as rotating group:
 C1(H1C,H1D,H1E), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C)
5.d Idealised tetrahedral OH refined as rotating group:
 O1(H1A), O1(H1B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O1 O 0.5850(14) 0.8600(8) 0.0892(3) 0.0571(19) Uani 1 1 d . U . . .
H1A H 0.6349 0.9512 0.0923 0.086 Uiso 0.24(9) 1 calc DGR . P . .
H1B H 0.6394 0.7768 0.1046 0.086 Uiso 0.76(9) 1 calc DGR . P A 1
N1 N 0.6907(19) 0.5150(9) 0.0989(4) 0.041(2) Uani 1 1 d D U . . .
H1 H 0.6624 0.6278 0.1046 0.049 Uiso 0.24(9) 1 calc R . P . .
N3 N 0.6885(19) 0.2090(9) 0.0724(4) 0.043(2) Uani 1 1 d D U . . .
H3 H 0.6579 0.0985 0.0592 0.052 Uiso 0.76(9) 1 calc R . P . .
C1 C 1.186(2) 0.5546(11) 0.1640(5) 0.043(16) Uani 1 1 d . . . . .
H1C H 1.1657 0.6850 0.1711 0.065 Uiso 1 1 calc GR . . . .
H1D H 1.2459 0.5377 0.1081 0.065 Uiso 1 1 calc GR . . . .
H1E H 1.2276 0.5088 0.2298 0.065 Uiso 1 1 calc GR . . . .
C2 C 0.6186(19) 0.3649(10) 0.0782(4) 0.043(2) Uani 1 1 d . U . . .
H2 H 0.5253 0.3678 0.0683 0.051 Uiso 1 1 calc R . . . .
C7 C 0.9411(14) 0.5487(6) 0.1327(3) 0.034(2) Uani 1 1 d . U . . .
H7 H 0.9401 0.6770 0.1444 0.041 Uiso 1 1 calc R . . . .
C8 C 0.8211(13) 0.4534(9) 0.1097(3) 0.038(3) Uani 1 1 d G U . . .
C9 C 0.8226(14) 0.2616(9) 0.0923(3) 0.030(2) Uani 1 1 d G U . . .
C4 C 0.9440(14) 0.1652(6) 0.0979(3) 0.033(2) Uani 1 1 d G U . . .
H4 H 0.9449 0.0369 0.0863 0.040 Uiso 1 1 calc R . . . .
C5 C 1.0639(14) 0.2605(8) 0.1210(3) 0.034(2) Uani 1 1 d G U . . .
C6 C 1.0625(13) 0.4523(8) 0.1384(3) 0.033(2) Uani 1 1 d G U . . .
C10 C 1.189(3) 0.1574(11) 0.1246(5) 0.057(2) Uani 1 1 d . U . . .
H10A H 1.2331 0.1663 0.1947 0.085 Uiso 1 1 calc GR . . . .
H10B H 1.2468 0.2089 0.0736 0.085 Uiso 1 1 calc GR . . . .
H10C H 1.1713 0.0286 0.1078 0.085 Uiso 1 1 calc GR . . . .
C12 C 0.493(2) 0.8734(12) 0.1689(5) 0.062(2) Uani 1 1 d . U . . .
H12A H 0.4301 0.7716 0.1618 0.093 Uiso 1 1 calc GR . . . .
H12B H 0.4449 0.9896 0.1615 0.093 Uiso 1 1 calc GR . . . .
H12C H 0.5402 0.8683 0.2377 0.093 Uiso 1 1 calc GR . . . .

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
O1 0.058(3) 0.052(2) 0.0615(19) 0.0009(15) 0.005(2) 0.000(2)
N1 0.041(4) 0.040(3) 0.041(2) 0.0013(18) 0.004(3) 0.002(3)
N3 0.044(4) 0.042(3) 0.043(2) -0.0010(18) -0.004(3) -0.002(3)
C1 0.03(5) 0.056(5) 0.043(3) -0.003(3) 0.009(7) -0.004(9)
C2 0.043(5) 0.044(3) 0.041(2) 0.001(2) 0.000(3) 0.000(3)
C7 0.034(5) 0.035(3) 0.034(2) 0.001(2) 0.007(3) 0.000(3)
C8 0.038(5) 0.039(4) 0.036(2) 0.001(2) 0.004(3) 0.001(3)
C9 0.030(5) 0.027(3) 0.033(2) 0.0018(19) 0.001(3) -0.002(3)
C4 0.033(4) 0.034(3) 0.034(2) -0.0018(19) 0.008(3) -0.001(3)
C5 0.034(4) 0.038(3) 0.0300(19) -0.0008(19) 0.006(3) 0.004(3)
C6 0.033(5) 0.035(3) 0.032(2) 0.001(2) 0.005(3) -0.001(3)
C10 0.057(4) 0.057(3) 0.056(2) 0.0011(18) 0.004(2) 0.001(2)
C12 0.062(4) 0.060(3) 0.063(2) -0.0021(18) 0.004(2) 0.000(2)

_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
O1 H1A 0.8200 . ?
O1 H1B 0.8200 . ?
O1 C12 1.41(2) . ?
N1 H1 0.8600 . ?
N1 C2 1.309(14) . ?
N1 C8 1.370(18) . ?
N3 H3 0.8600 . ?
N3 C2 1.319(15) . ?
N3 C9 1.394(18) . ?
C1 H1C 0.9600 . ?
C1 H1D 0.9600 . ?
C1 H1E 0.9600 . ?
C1 C6 1.45(2) . ?
C2 H2 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.3900 . ?
C7 C6 1.3900 . ?
C8 C9 1.3900 . ?
C9 C4 1.3900 . ?
C4 H4 0.9300 . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C5 C10 1.45(2) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

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
H1A O1 H1B 100.3 . . ?
C12 O1 H1A 109.5 . . ?
C12 O1 H1B 109.5 . . ?
C2 N1 H1 127.5 . . ?
C2 N1 C8 105.1(9) . . ?
C8 N1 H1 127.5 . . ?
C2 N3 H3 127.3 . . ?
C2 N3 C9 105.4(10) . . ?
C9 N3 H3 127.3 . . ?
H1C C1 H1D 109.5 . . ?
H1C C1 H1E 109.5 . . ?
H1D C1 H1E 109.5 . . ?
C6 C1 H1C 109.5 . . ?
C6 C1 H1D 109.5 . . ?
C6 C1 H1E 109.5 . . ?
N1 C2 N3 114.8(16) . . ?
N1 C2 H2 122.6 . . ?
N3 C2 H2 122.6 . . ?
C8 C7 H7 120.0 . . ?
C8 C7 C6 120.0 . . ?
C6 C7 H7 120.0 . . ?
N1 C8 C7 131.2(6) . . ?
N1 C8 C9 108.8(6) . . ?
C7 C8 C9 120.0 . . ?
C8 C9 N3 106.0(6) . . ?
C4 C9 N3 134.0(6) . . ?
C4 C9 C8 120.0 . . ?
C9 C4 H4 120.0 . . ?
C9 C4 C5 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C10 118.9(7) . . ?
C6 C5 C4 120.0 . . ?
C6 C5 C10 121.0(7) . . ?
C7 C6 C1 118.9(7) . . ?
C5 C6 C1 121.1(7) . . ?
C5 C6 C7 120.0 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
N1 C8 C9 N3 -1.0(3) . . . . ?
N1 C8 C9 C4 179.6(4) . . . . ?
N3 C9 C4 C5 -179.3(5) . . . . ?
C2 N1 C8 C7 -179.3(3) . . . . ?
C2 N1 C8 C9 1.2(5) . . . . ?
C2 N3 C9 C8 0.4(4) . . . . ?
C2 N3 C9 C4 179.7(3) . . . . ?
C7 C8 C9 N3 179.5(4) . . . . ?
C7 C8 C9 C4 0.0 . . . . ?
C8 N1 C2 N3 -1.0(6) . . . . ?
C8 C7 C6 C1 -179.2(4) . . . . ?
C8 C7 C6 C5 0.0 . . . . ?
C8 C9 C4 C5 0.0 . . . . ?
C9 N3 C2 N1 0.4(6) . . . . ?
C9 C4 C5 C6 0.0 . . . . ?
C9 C4 C5 C10 -178.9(4) . . . . ?
C4 C5 C6 C1 179.2(4) . . . . ?
C4 C5 C6 C7 0.0 . . . . ?
C6 C7 C8 N1 -179.4(5) . . . . ?
C6 C7 C8 C9 0.0 . . . . ?
C10 C5 C6 C1 -2.0(5) . . . . ?
C10 C5 C6 C7 178.9(4) . . . . ?

_shelx_res_file                  
;
    37b.res created by SHELXL-2014/7

TITL 37b in P21/c #14
REM reset to P21/c #14
CELL 0.71073 9.960062 7.157401 12.579002 90 93.7147 90
ZERR 4 0.01249 0.000995 0.000802 0 0.0202 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O
UNIT 40 56 8 4
EQIV $1 +X,1+Y,+Z
DFIX 1.94 H1a N3_$1
DFIX 1.94 H1b N1
ISOR 0.003 0.002 C10 C4 C8 C9 C5 C6 O1 C12 N3 N1 C2 C7

L.S. 44
PLAN  5
TEMP 22.85
BOND
MORE -1
CONF
BOND $H
fmap 2
acta 52
OMIT 2 5 8
OMIT 2 5 9
OMIT 2 3 4
OMIT 2 4 0
OMIT -3 1 13
OMIT -3 0 10
OMIT 2 6 7
OMIT 1 3 3
OMIT -3 2 14
OMIT -3 3 9
REM <olex2.extras>
REM <HklSrc "%.\\37b.hkl">
REM </olex2.extras>

WGHT    0.082700    1.330200
FVAR      13.62282   0.24059
O1    4    0.585022    0.859984    0.089153    11.00000    0.05771    0.05227 =
         0.06150    0.00090    0.00498    0.00047
AFIX 147
H1A   2    0.634896    0.951241    0.092260    21.00000   -1.50000
AFIX 147
PART 1
H1B   2    0.639424    0.776766    0.104581   -21.00000   -1.50000
AFIX   0
PART 0
N1    3    0.690711    0.515014    0.098910    11.00000    0.04128    0.04005 =
         0.04061    0.00131    0.00402    0.00231
AFIX  43
H1    2    0.662360    0.627849    0.104556    21.00000   -1.20000
AFIX   0
N3    3    0.688529    0.209046    0.072421    11.00000    0.04358    0.04167 =
         0.04333   -0.00099   -0.00370   -0.00163
AFIX  43
H3    2    0.657917    0.098530    0.059238   -21.00000   -1.20000
AFIX   0
C1    1    1.185816    0.554561    0.164020    11.00000    0.03185    0.05627 =
         0.04264   -0.00340    0.00867   -0.00432
AFIX 137
H1C   2    1.165734    0.684983    0.171084    11.00000   -1.50000
H1D   2    1.245869    0.537723    0.108100    11.00000   -1.50000
H1E   2    1.227598    0.508780    0.229850    11.00000   -1.50000
AFIX   0
C2    1    0.618609    0.364875    0.078180    11.00000    0.04271    0.04426 =
         0.04062    0.00081    0.00036    0.00038
AFIX  43
H2    2    0.525288    0.367843    0.068275    11.00000   -1.20000
AFIX  66
C7    1    0.941091    0.548702    0.132743    11.00000    0.03450    0.03495 =
         0.03440    0.00147    0.00678   -0.00022
AFIX  43
H7    2    0.940124    0.676994    0.144391    11.00000   -1.20000
AFIX  65
C8    1    0.821143    0.453381    0.109663    11.00000    0.03835    0.03935 =
         0.03629    0.00096    0.00353    0.00094
C9    1    0.822587    0.261634    0.092253    11.00000    0.02996    0.02680 =
         0.03264    0.00185    0.00086   -0.00248
C4    1    0.943979    0.165207    0.097924    11.00000    0.03292    0.03392 =
         0.03411   -0.00183    0.00839   -0.00146
AFIX  43
H4    2    0.944944    0.036915    0.086275    11.00000   -1.20000
AFIX  65
C5    1    1.063927    0.260526    0.121004    11.00000    0.03404    0.03767 =
         0.03001   -0.00083    0.00572    0.00352
C6    1    1.062485    0.452273    0.138414    11.00000    0.03319    0.03467 =
         0.03205    0.00136    0.00477   -0.00116
AFIX   0
C10   1    1.189346    0.157394    0.124567    11.00000    0.05702    0.05706 =
         0.05568    0.00108    0.00405    0.00071
AFIX 137
H10A  2    1.233072    0.166326    0.194669    11.00000   -1.50000
H10B  2    1.246771    0.208923    0.073606    11.00000   -1.50000
H10C  2    1.171279    0.028615    0.107786    11.00000   -1.50000
AFIX   0
C12   1    0.492723    0.873436    0.168858    11.00000    0.06191    0.06041 =
         0.06306   -0.00205    0.00364   -0.00011
AFIX 137
H12A  2    0.430067    0.771578    0.161832    11.00000   -1.50000
H12B  2    0.444882    0.989629    0.161456    11.00000   -1.50000
H12C  2    0.540234    0.868280    0.237676    11.00000   -1.50000
AFIX   0
HKLF 4

REM  37b in P21/c #14
REM R1 =  0.0644 for     277 Fo > 4sig(Fo)  and  0.1198 for all     449 data
REM    111 parameters refined using     74 restraints

END

WGHT      0.0828      1.3290

REM Highest difference peak  0.155,  deepest hole -0.126,  1-sigma level  0.040
Q1    1   0.7769  0.8660  0.1158  11.00000  0.05    0.15
Q2    1   0.9635 -0.1395  0.0594  11.00000  0.05    0.15
Q3    1   0.4085  0.8620  0.0785  11.00000  0.05    0.14
Q4    1   0.5500  0.8753  0.0462  11.00000  0.05    0.14
Q5    1   0.5722  0.5874  0.1467  11.00000  0.05    0.13
;
_shelx_res_checksum              32912
_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_dMBzIm_MeOH_1_53GPa
_database_code_depnum_ccdc_archive 'CCDC 1451568'
_audit_update_record             
;
2016-03-29 deposited with the CCDC.
2016-04-01 downloaded from the CCDC.
;
_audit_creation_date             2016-03-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            '5,6-dimethylbenzimidazole methanol solvate'
_chemical_name_systematic        '5,6-dimethylbenzimidazole methanol solvate'
_chemical_formula_moiety         'C H4 O, C9 H10 N2'
_chemical_formula_sum            'C10 H14 N2 O'
_chemical_formula_weight         178.23
_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 0.0033 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'
O O 0.0106 0.0060 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.110(6)
_cell_length_b                   7.1000(7)
_cell_length_c                   6.6984(10)
_cell_angle_alpha                114.720(12)
_cell_angle_beta                 94.61(2)
_cell_angle_gamma                90.202(19)
_cell_volume                     435.0(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    646
_cell_measurement_temperature    296
_cell_measurement_theta_max      25.7930
_cell_measurement_theta_min      3.9490
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55066
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             192
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_special_details           
;
 Data were collected at room temperature and pressure of 1.53(2) GPa
 (1530000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique.
 Pressure was determined by monitoring the shift of the ruby
 R1-fluorescence line.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.248
_diffrn_reflns_Laue_measured_fraction_max 0.233
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2321
_diffrn_reflns_point_group_measured_fraction_full 0.248
_diffrn_reflns_point_group_measured_fraction_max 0.233
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.877
_diffrn_reflns_theta_min         3.972
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 16.2413
_diffrn_measured_fraction_theta_full 0.248
_diffrn_measured_fraction_theta_max 0.233
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 phi    -35.00   19.60   0.7000   34.0000
omega____ theta____ kappa____ phi______ frames
   0.0000  -30.0000    0.0000     -     78

#__ type_ start__ end____ width___ exp.time_
  2 phi    140.00  199.50   0.7000   34.0000
omega____ theta____ kappa____ phi______ frames
   0.0000  -30.0000    0.0000     -     85

#__ type_ start__ end____ width___ exp.time_
  3 phi    160.00  216.70   0.7000   34.0000
omega____ theta____ kappa____ phi______ frames
   0.0000   30.0000    0.0000     -     81

#__ type_ start__ end____ width___ exp.time_
  4 phi    -20.00   34.60   0.7000   34.0000
omega____ theta____ kappa____ phi______ frames
   0.0000   30.0000    0.0000     -     78

#__ type_ start__ end____ width___ exp.time_
  5 omega  -24.00   23.60   0.7000   34.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   39.4600  -12.9000 68

#__ type_ start__ end____ width___ exp.time_
  6 omega  -24.00   23.60   0.7000   34.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   39.4600  167.1000 68

#__ type_ start__ end____ width___ exp.time_
  7 omega  -50.00    9.50   0.7000   34.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000   39.4600  167.1000 85

#__ type_ start__ end____ width___ exp.time_
  8 omega  -50.00    9.50   0.7000   34.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000   39.4600  -12.9000 85

#__ type_ start__ end____ width___ exp.time_
  9 omega  -64.00   -8.00   0.7000   34.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000   81.4000  -28.9000 80

#__ type_ start__ end____ width___ exp.time_
 10 omega  -64.00   -8.00   0.7000   34.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000   81.4000  151.1000 80

#__ type_ start__ end____ width___ exp.time_
 11 omega  -19.00    7.60   0.7000   34.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   81.4000  151.1000 38

#__ type_ start__ end____ width___ exp.time_
 12 omega  -19.00    7.60   0.7000   34.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   81.4000  -28.9000 38

#__ type_ start__ end____ width___ exp.time_
 13 omega  -43.00  -21.30   0.7000   34.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  134.6000  -56.9000 31

#__ type_ start__ end____ width___ exp.time_
 14 omega  -43.00  -21.30   0.7000   34.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  134.6000  123.1000 31

#__ type_ start__ end____ width___ exp.time_
 15 omega  -90.00  -36.10   0.7000   34.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000  134.6000  123.1000 77

#__ type_ start__ end____ width___ exp.time_
 16 omega  -90.00  -36.10   0.7000   34.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000  134.6000  -56.9000 77
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω and π scans'
_diffrn_orient_matrix_UB_11      -0.0680039000
_diffrn_orient_matrix_UB_12      0.0098580000
_diffrn_orient_matrix_UB_13      -0.0278791000
_diffrn_orient_matrix_UB_21      -0.0173033000
_diffrn_orient_matrix_UB_22      -0.0184067000
_diffrn_orient_matrix_UB_23      0.0910283000
_diffrn_orient_matrix_UB_31      0.0061986000
_diffrn_orient_matrix_UB_32      0.1080734000
_diffrn_orient_matrix_UB_33      0.0680958000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                324
_reflns_number_total             437
_reflns_odcompleteness_completeness 23.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.82
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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)'
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         437
_refine_ls_number_restraints     186
_refine_ls_R_factor_all          0.0834
_refine_ls_R_factor_gt           0.0631
_refine_ls_restrained_S_all      0.910
_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)+(0.1228P)²+0.0512P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1619
_refine_ls_wR_factor_ref         0.1812
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(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
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
Uanis(C8) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C4) \\sim
Ueq, Uanis(N3) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C2)
\\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(O1) \\sim Ueq, Uanis(C11) \\sim Ueq,
Uanis(N1) \\sim Ueq, Uanis(C10) \\sim Ueq: with sigma of 0.2 and sigma for
terminal atoms of 0.3
4.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C7(H7), C4(H4)
4.b Fitted hexagon refined as free rotating group:
 C9(C8,C7,C6,C5,C4)
4.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
4.d Idealised tetrahedral OH refined as rotating group:
 O1(H1A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O1 O 0.5809(12) 0.7025(5) 0.6654(7) 0.062(10) Uani 1 1 d . U . . .
H1A H 0.5978 0.8154 0.6650 0.092 Uiso 1 1 calc GR . . . .
C12 C 0.489(2) 0.7268(9) 0.8228(13) 0.063(14) Uani 1 1 d . U . . .
H12A H 0.4550 0.5928 0.8023 0.094 Uiso 1 1 calc GR . . . .
H12B H 0.4167 0.8072 0.8037 0.094 Uiso 1 1 calc GR . . . .
H12C H 0.5324 0.7969 0.9689 0.094 Uiso 1 1 calc GR . . . .
N1 N 0.695(2) 0.3537(11) 0.6580(14) 0.041(8) Uani 1 1 d . U . . .
H1 H 0.6658 0.4554 0.6318 0.049 Uiso 1 1 calc R . . . .
N3 N 0.6991(19) 0.0649(8) 0.7152(10) 0.042(9) Uani 1 1 d . U . . .
C2 C 0.621(2) 0.1996(9) 0.6696(15) 0.043(9) Uani 1 1 d . U . . .
H2 H 0.5286 0.1878 0.6490 0.051 Uiso 1 1 calc R . . . .
C9 C 0.8297(11) 0.1366(8) 0.7325(8) 0.036(9) Uani 1 1 d . U . . .
C8 C 0.8319(11) 0.3161(9) 0.6973(10) 0.035(8) Uani 1 1 d G U . . .
C7 C 0.9525(12) 0.4142(5) 0.7040(7) 0.036(8) Uani 1 1 d G U . . .
H7 H 0.9540 0.5342 0.6805 0.043 Uiso 1 1 calc R . . . .
C6 C 1.0709(11) 0.3327(7) 0.7459(8) 0.043(8) Uani 1 1 d G U . . .
C5 C 1.0687(11) 0.1532(8) 0.7811(11) 0.039(9) Uani 1 1 d G U . . .
C4 C 0.9481(12) 0.0552(6) 0.7744(9) 0.035(9) Uani 1 1 d G U . . .
H4 H 0.9466 -0.0649 0.7979 0.042 Uiso 1 1 calc R . . . .
C10 C 1.194(2) 0.0734(12) 0.8334(18) 0.049(9) Uani 1 1 d . U . . .
H10A H 1.2530 0.0572 0.7232 0.074 Uiso 1 1 calc GR . . . .
H10B H 1.1765 -0.0585 0.8362 0.074 Uiso 1 1 calc GR . . . .
H10C H 1.2330 0.1692 0.9753 0.074 Uiso 1 1 calc GR . . . .
C11 C 1.1963(19) 0.4388(9) 0.7456(12) 0.051(9) Uani 1 1 d . U . . .
H11A H 1.2421 0.3519 0.6214 0.077 Uiso 1 1 calc GR . . . .
H11B H 1.2511 0.4664 0.8795 0.077 Uiso 1 1 calc GR . . . .
H11C H 1.1776 0.5673 0.7358 0.077 Uiso 1 1 calc GR . . . .

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
O1 0.11(3) 0.0311(18) 0.052(3) 0.0175(18) 0.029(8) -0.008(4)
C12 0.09(4) 0.039(3) 0.057(5) 0.017(3) 0.023(14) 0.002(7)
N1 0.06(2) 0.034(3) 0.042(5) 0.024(3) 0.014(9) 0.004(7)
N3 0.06(3) 0.029(2) 0.042(4) 0.020(2) 0.015(9) 0.010(6)
C2 0.05(2) 0.041(4) 0.035(5) 0.015(3) 0.012(11) 0.000(8)
C9 0.06(2) 0.022(4) 0.030(6) 0.015(3) 0.012(13) 0.006(10)
C8 0.06(2) 0.025(3) 0.026(5) 0.010(3) 0.017(10) 0.006(8)
C7 0.06(2) 0.023(3) 0.022(4) 0.007(2) 0.014(8) -0.012(6)
C6 0.06(2) 0.034(3) 0.034(5) 0.012(3) 0.016(9) -0.004(8)
C5 0.06(3) 0.036(4) 0.022(5) 0.010(3) 0.018(10) 0.005(8)
C4 0.06(2) 0.024(3) 0.028(5) 0.011(3) 0.015(10) -0.002(8)
C10 0.06(3) 0.053(5) 0.042(6) 0.025(4) 0.004(12) -0.006(10)
C11 0.07(2) 0.049(3) 0.037(4) 0.019(3) 0.002(9) -0.014(8)

_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
O1 H1A 0.8200 . ?
O1 C12 1.420(12) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
N1 H1 0.8600 . ?
N1 C2 1.359(11) . ?
N1 C8 1.43(2) . ?
N3 C2 1.36(2) . ?
N3 C9 1.392(18) . ?
C2 H2 0.9300 . ?
C9 C8 1.3900 . ?
C9 C4 1.3900 . ?
C8 C7 1.3900 . ?
C7 H7 0.9300 . ?
C7 C6 1.3900 . ?
C6 C5 1.3900 . ?
C6 C11 1.473(15) . ?
C5 C4 1.3900 . ?
C5 C10 1.46(2) . ?
C4 H4 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

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
C12 O1 H1A 109.5 . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C2 N1 H1 126.2 . . ?
C2 N1 C8 107.5(14) . . ?
C8 N1 H1 126.2 . . ?
C2 N3 C9 106.5(7) . . ?
N1 C2 H2 124.5 . . ?
N3 C2 N1 110.9(19) . . ?
N3 C2 H2 124.5 . . ?
C8 C9 N3 109.9(7) . . ?
C8 C9 C4 120.0 . . ?
C4 C9 N3 130.1(7) . . ?
C9 C8 N1 105.1(6) . . ?
C9 C8 C7 120.0 . . ?
C7 C8 N1 134.9(6) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 C8 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C6 C11 118.1(7) . . ?
C5 C6 C7 120.0 . . ?
C5 C6 C11 121.9(7) . . ?
C6 C5 C4 120.0 . . ?
C6 C5 C10 119.5(6) . . ?
C4 C5 C10 120.5(6) . . ?
C9 C4 H4 120.0 . . ?
C5 C4 C9 120.0 . . ?
C5 C4 H4 120.0 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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
N1 C8 C7 C6 -179.3(9) . . . . ?
N3 C9 C8 N1 0.3(5) . . . . ?
N3 C9 C8 C7 -179.2(4) . . . . ?
N3 C9 C4 C5 179.0(5) . . . . ?
C2 N1 C8 C9 -0.4(7) . . . . ?
C2 N1 C8 C7 179.0(4) . . . . ?
C2 N3 C9 C8 0.0(4) . . . . ?
C2 N3 C9 C4 -179.1(5) . . . . ?
C9 N3 C2 N1 -0.3(7) . . . . ?
C9 C8 C7 C6 0.0 . . . . ?
C8 N1 C2 N3 0.4(8) . . . . ?
C8 C9 C4 C5 0.0 . . . . ?
C8 C7 C6 C5 0.0 . . . . ?
C8 C7 C6 C11 178.4(4) . . . . ?
C7 C6 C5 C4 0.0 . . . . ?
C7 C6 C5 C10 -177.7(8) . . . . ?
C6 C5 C4 C9 0.0 . . . . ?
C4 C9 C8 N1 179.5(7) . . . . ?
C4 C9 C8 C7 0.0 . . . . ?
C10 C5 C4 C9 177.6(8) . . . . ?
C11 C6 C5 C4 -178.4(4) . . . . ?
C11 C6 C5 C10 4.0(7) . . . . ?

_shelx_res_file                  
;
    34parok.res created by SHELXL-2014/7

TITL 34parok in P-1 #2
REM reset to P-1 #2
CELL 0.71073 10.110174 7.10002 6.698442 114.72 94.6097 90.2021
ZERR 2 0.005542 0.000701 0.000952 0.0116 0.0233 0.0189
LATT 1
SFAC C H N O
UNIT 20 28 4 2
DELU
SIMU
ISOR 0.2 0.3 C8 C5 C12 C4 N3 C6 C7 C2 C9 O1 C11 N1 C10

L.S. 47
PLAN  5
BOND
MORE -1
BOND $H
CONF
fmap 2
acta 52
OMIT -1 3 2
OMIT 1 1 3
OMIT 0 1 3
OMIT -3 -4 5
OMIT -1 -5 2
OMIT -4 2 5
OMIT -2 -7 3
OMIT -1 -2 4
OMIT -1 1 7
REM <olex2.extras>
REM <HklSrc "%.\\34parok.hkl">
REM </olex2.extras>

WGHT    0.122800    0.051200
FVAR      10.95832
O1    4    0.580937    0.702499    0.665360    11.00000    0.10637    0.03107 =
         0.05155    0.01752    0.02903   -0.00773
AFIX 147
H1A   2    0.597759    0.815406    0.664974    11.00000   -1.50000
AFIX   0
C12   1    0.488807    0.726827    0.822810    11.00000    0.09156    0.03882 =
         0.05709    0.01672    0.02324    0.00207
AFIX 137
H12A  2    0.454975    0.592836    0.802261    11.00000   -1.50000
H12B  2    0.416739    0.807162    0.803705    11.00000   -1.50000
H12C  2    0.532423    0.796929    0.968908    11.00000   -1.50000
AFIX   0

N1    3    0.695309    0.353726    0.657979    11.00000    0.05586    0.03354 =
         0.04167    0.02353    0.01364    0.00392
AFIX  43
H1    2    0.665803    0.455371    0.631785    11.00000   -1.20000
AFIX   0
N3    3    0.699113    0.064900    0.715214    11.00000    0.06308    0.02880 =
         0.04211    0.01950    0.01461    0.00994
C2    1    0.620832    0.199566    0.669570    11.00000    0.05247    0.04078 =
         0.03519    0.01511    0.01217   -0.00020
AFIX  43
H2    2    0.528586    0.187810    0.649003    11.00000   -1.20000
AFIX  66
C9    1    0.829692    0.136619    0.732513    11.00000    0.06216    0.02214 =
         0.03022    0.01467    0.01205    0.00646
C8    1    0.831920    0.316118    0.697334    11.00000    0.05531    0.02479 =
         0.02578    0.00955    0.01689    0.00595
C7    1    0.952516    0.414150    0.704041    11.00000    0.06131    0.02348 =
         0.02218    0.00688    0.01360   -0.01249
AFIX  43
H7    2    0.954006    0.534247    0.680503    11.00000   -1.20000
AFIX  65
C6    1    1.070884    0.332683    0.745928    11.00000    0.06087    0.03365 =
         0.03387    0.01218    0.01596   -0.00414
C5    1    1.068658    0.153185    0.781108    11.00000    0.06040    0.03608 =
         0.02232    0.01036    0.01834    0.00464
C4    1    0.948063    0.055150    0.774401    11.00000    0.05551    0.02407 =
         0.02751    0.01071    0.01498   -0.00204
AFIX  43
H4    2    0.946573   -0.064947    0.797938    11.00000   -1.20000
AFIX   0
C10   1    1.193510    0.073438    0.833424    11.00000    0.05845    0.05281 =
         0.04201    0.02504    0.00385   -0.00572
AFIX 137
H10A  2    1.253029    0.057196    0.723161    11.00000   -1.50000
H10B  2    1.176453   -0.058497    0.836215    11.00000   -1.50000
H10C  2    1.233046    0.169242    0.975255    11.00000   -1.50000
AFIX   0
C11   1    1.196325    0.438806    0.745625    11.00000    0.06666    0.04946 =
         0.03733    0.01920    0.00173   -0.01359
AFIX 137
H11A  2    1.242068    0.351912    0.621378    11.00000   -1.50000
H11B  2    1.251065    0.466388    0.879520    11.00000   -1.50000
H11C  2    1.177570    0.567259    0.735779    11.00000   -1.50000
AFIX   0
HKLF 4

REM  34parok in P-1 #2
REM R1 =  0.0631 for     324 Fo > 4sig(Fo)  and  0.0834 for all     437 data
REM    110 parameters refined using    186 restraints

END

WGHT      0.1228      0.0512

REM Highest difference peak  0.185,  deepest hole -0.129,  1-sigma level  0.045
Q1    1   1.0000  0.5000  1.0000  10.50000  0.05    0.19
Q2    1   1.2331  0.5564  1.0311  11.00000  0.05    0.18
Q3    1   1.2170  0.3377  0.4419  11.00000  0.05    0.18
Q4    1   0.8956 -0.2066  0.5571  11.00000  0.05    0.16
Q5    1   0.9284 -0.0520  0.5007  11.00000  0.05    0.15
;
_shelx_res_checksum              81717
_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_dMBzIm_MeOH_1_90GPa
_database_code_depnum_ccdc_archive 'CCDC 1451569'
_audit_update_record             
;
2016-03-29 deposited with the CCDC.
2016-04-01 downloaded from the CCDC.
;
_audit_creation_date             2016-03-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            '5,6-dimethylbenzimidazole methanol solvate'
_chemical_name_systematic        '5,6-dimethylbenzimidazole methanol solvate'
_chemical_formula_moiety         'C H4 O, C9 H10 N2'
_chemical_formula_sum            'C10 H14 N2 O'
_chemical_formula_weight         178.23
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'
O O 0.0106 0.0060 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.037(2)
_cell_length_b                   7.0477(10)
_cell_length_c                   6.6292(10)
_cell_angle_alpha                115.381(14)
_cell_angle_beta                 94.711(14)
_cell_angle_gamma                90.103(14)
_cell_volume                     421.88(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    951
_cell_measurement_temperature    296
_cell_measurement_theta_max      28.1771
_cell_measurement_theta_min      3.1956
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40172
_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_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             192
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.35
_exptl_special_details           
;
 Data were collected at room temperature and pressure of 1.90(2) GPa
 (1900000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique.
 Pressure was determined by monitoring the shift of the ruby
 R1-fluorescence line.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1170
_diffrn_reflns_av_unetI/netI     0.0694
_diffrn_reflns_Laue_measured_fraction_full 0.292
_diffrn_reflns_Laue_measured_fraction_max 0.250
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            2970
_diffrn_reflns_point_group_measured_fraction_full 0.292
_diffrn_reflns_point_group_measured_fraction_max 0.250
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.239
_diffrn_reflns_theta_min         3.202
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measured_fraction_theta_full 0.292
_diffrn_measured_fraction_theta_max 0.250
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 phi    -35.00   19.75   0.7500   26.0000
omega____ theta____ kappa____ phi______ frames
   0.0000  -30.0000    0.0000     -     73

#__ type_ start__ end____ width___ exp.time_
  2 phi    140.00  200.00   0.7500   28.0000
omega____ theta____ kappa____ phi______ frames
   0.0000  -30.0000    0.0000     -     80

#__ type_ start__ end____ width___ exp.time_
  3 phi    160.00  217.00   0.7500   28.0000
omega____ theta____ kappa____ phi______ frames
   0.0000   30.0000    0.0000     -     76

#__ type_ start__ end____ width___ exp.time_
  4 phi    -20.00   34.75   0.7500   28.0000
omega____ theta____ kappa____ phi______ frames
   0.0000   30.0000    0.0000     -     73

#__ type_ start__ end____ width___ exp.time_
  5 omega  -24.00   24.00   0.7500   28.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   39.4600  -12.9000 64

#__ type_ start__ end____ width___ exp.time_
  6 omega  -24.00   24.00   0.7500   28.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   39.4600  167.1000 64

#__ type_ start__ end____ width___ exp.time_
  7 omega  -50.00   10.00   0.7500   28.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000   39.4600  167.1000 80

#__ type_ start__ end____ width___ exp.time_
  8 omega  -50.00   10.00   0.7500   28.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000   39.4600  -12.9000 80

#__ type_ start__ end____ width___ exp.time_
  9 omega  -64.00   -8.50   0.7500   28.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000   81.4000  -28.9000 74

#__ type_ start__ end____ width___ exp.time_
 10 omega  -64.00   -8.50   0.7500   28.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000   81.4000  151.1000 74

#__ type_ start__ end____ width___ exp.time_
 11 omega  -19.00    8.00   0.7500   28.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   81.4000  151.1000 36

#__ type_ start__ end____ width___ exp.time_
 12 omega  -19.00    8.00   0.7500   28.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   81.4000  -28.9000 36

#__ type_ start__ end____ width___ exp.time_
 13 omega  -43.00  -21.25   0.7500   28.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  134.6000  -56.9000 29

#__ type_ start__ end____ width___ exp.time_
 14 omega  -43.00  -21.25   0.7500   28.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  134.6000  123.1000 29

#__ type_ start__ end____ width___ exp.time_
 15 omega  -90.00  -36.00   0.7500   28.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000  134.6000  123.1000 72

#__ type_ start__ end____ width___ exp.time_
 16 omega  -90.00  -36.00   0.7500   28.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000  134.6000  -56.9000 72
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω and π scans'
_diffrn_orient_matrix_UB_11      -0.0357841000
_diffrn_orient_matrix_UB_12      0.0307435000
_diffrn_orient_matrix_UB_13      0.0575599000
_diffrn_orient_matrix_UB_21      0.0178374000
_diffrn_orient_matrix_UB_22      -0.0782565000
_diffrn_orient_matrix_UB_23      0.0366686000
_diffrn_orient_matrix_UB_31      0.1120064000
_diffrn_orient_matrix_UB_32      0.0732156000
_diffrn_orient_matrix_UB_33      0.0194639000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                355
_reflns_number_total             520
_reflns_odcompleteness_completeness 28.24
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       
;
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)'
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     114
_refine_ls_number_reflns         520
_refine_ls_number_restraints     78
_refine_ls_R_factor_all          0.0925
_refine_ls_R_factor_gt           0.0612
_refine_ls_restrained_S_all      0.996
_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)+(0.0900P)²+0.2957P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1529
_refine_ls_wR_factor_ref         0.1813
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C9) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(N3) \\sim
Ueq, Uanis(C10) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C2)
\\sim Ueq, Uanis(O1) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(N1) \\sim Ueq,
Uanis(C11) \\sim Ueq, Uanis(C8) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C7(H7)
3.b Fitted hexagon refined as free rotating group:
 C4(C9,C8,C7,C6,C5)
3.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
3.d Idealised tetrahedral OH refined as rotating group:
 O1(H1A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
O1 O 0.5781(11) 0.7031(8) 0.6669(9) 0.053(5) Uani 1 1 d . U . . .
H1A H 0.6123 0.8177 0.6922 0.080 Uiso 1 1 calc GR . . . .
C12 C 0.4916(19) 0.7276(15) 0.8237(15) 0.055(6) Uani 1 1 d . U . . .
H12A H 0.5363 0.8046 0.9709 0.083 Uiso 1 1 calc GR . . . .
H12B H 0.4613 0.5920 0.8072 0.083 Uiso 1 1 calc GR . . . .
H12C H 0.4163 0.8033 0.8033 0.083 Uiso 1 1 calc GR . . . .
N1 N 0.6992(12) 0.3560(10) 0.6551(10) 0.043(5) Uani 1 1 d . U . . .
H1 H 0.652(12) 0.473(10) 0.656(11) 0.060(19) Uiso 1 1 d . . . . .
N3 N 0.6948(12) 0.0655(8) 0.7158(10) 0.040(5) Uani 1 1 d . U . . .
C2 C 0.6221(15) 0.2035(11) 0.6714(11) 0.042(5) Uani 1 1 d . U . . .
H2 H 0.5291 0.1970 0.6535 0.051 Uiso 1 1 calc R . . . .
C4 C 0.9447(7) 0.0545(5) 0.7752(6) 0.028(5) Uani 1 1 d . U . . .
H4 H 0.9448 -0.0659 0.7996 0.034 Uiso 1 1 calc R . . . .
C9 C 0.8242(7) 0.1337(6) 0.7331(6) 0.032(5) Uani 1 1 d G U . . .
C8 C 0.8240(7) 0.3138(6) 0.6966(7) 0.032(5) Uani 1 1 d G U . . .
C7 C 0.9443(7) 0.4147(5) 0.7023(7) 0.039(5) Uani 1 1 d G U . . .
H7 H 0.9442 0.5352 0.6779 0.047 Uiso 1 1 calc R . . . .
C6 C 1.0648(7) 0.3356(6) 0.7445(7) 0.031(5) Uani 1 1 d G U . . .
C5 C 1.0650(7) 0.1555(6) 0.7809(6) 0.028(5) Uani 1 1 d G U . . .
C10 C 1.1969(14) 0.0733(11) 0.8318(12) 0.048(5) Uani 1 1 d . U . . .
H10A H 1.1824 -0.0659 0.8200 0.071 Uiso 1 1 calc GR . . . .
H10B H 1.2337 0.1642 0.9810 0.071 Uiso 1 1 calc GR . . . .
H10C H 1.2582 0.0696 0.7264 0.071 Uiso 1 1 calc GR . . . .
C11 C 1.1965(17) 0.4396(12) 0.7398(13) 0.044(6) Uani 1 1 d . U . . .
H11A H 1.2488 0.4810 0.8810 0.065 Uiso 1 1 calc GR . . . .
H11B H 1.1791 0.5614 0.7135 0.065 Uiso 1 1 calc GR . . . .
H11C H 1.2449 0.3421 0.6219 0.065 Uiso 1 1 calc GR . . . .

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
O1 0.060(10) 0.041(3) 0.055(3) 0.018(2) -0.004(5) 0.014(5)
C12 0.056(11) 0.050(4) 0.064(5) 0.028(4) 0.002(7) 0.006(6)
N1 0.044(11) 0.034(3) 0.049(4) 0.018(3) -0.010(5) 0.006(5)
N3 0.047(11) 0.038(3) 0.037(3) 0.019(2) -0.004(5) 0.005(5)
C2 0.045(11) 0.044(4) 0.039(4) 0.021(3) -0.010(6) 0.002(6)
C4 0.033(11) 0.021(3) 0.033(4) 0.015(3) -0.003(6) -0.003(5)
C9 0.029(11) 0.028(3) 0.034(4) 0.010(3) -0.004(6) 0.000(6)
C8 0.029(11) 0.033(4) 0.033(4) 0.015(3) -0.005(6) 0.000(6)
C7 0.038(11) 0.033(4) 0.041(4) 0.012(3) -0.007(6) 0.009(5)
C6 0.033(11) 0.029(4) 0.033(4) 0.016(3) -0.006(6) -0.014(6)
C5 0.022(11) 0.026(4) 0.033(4) 0.011(3) -0.010(6) -0.006(5)
C10 0.046(11) 0.055(4) 0.040(4) 0.020(3) -0.005(6) 0.012(6)
C11 0.042(11) 0.041(4) 0.042(4) 0.013(3) -0.001(6) -0.002(6)

_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
O1 H1A 0.8200 . ?
O1 C12 1.36(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
N1 H1 0.95(5) . ?
N1 C2 1.369(18) . ?
N1 C8 1.323(10) . ?
N3 C2 1.334(7) . ?
N3 C9 1.363(15) . ?
C2 H2 0.9300 . ?
C4 H4 0.9300 . ?
C4 C9 1.3900 . ?
C4 C5 1.3900 . ?
C9 C8 1.3900 . ?
C8 C7 1.3900 . ?
C7 H7 0.9300 . ?
C7 C6 1.3900 . ?
C6 C5 1.3900 . ?
C6 C11 1.52(2) . ?
C5 C10 1.516(9) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

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
C12 O1 H1A 109.5 . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C2 N1 H1 115(9) . . ?
C8 N1 H1 138(8) . . ?
C8 N1 C2 105.1(6) . . ?
C2 N3 C9 104.8(10) . . ?
N1 C2 H2 123.6 . . ?
N3 C2 N1 112.7(12) . . ?
N3 C2 H2 123.6 . . ?
C9 C4 H4 120.0 . . ?
C9 C4 C5 120.0 . . ?
C5 C4 H4 120.0 . . ?
N3 C9 C4 131.8(4) . . ?
N3 C9 C8 108.2(4) . . ?
C4 C9 C8 120.0 . . ?
N1 C8 C9 109.2(6) . . ?
N1 C8 C7 130.8(6) . . ?
C7 C8 C9 120.0 . . ?
C8 C7 H7 120.0 . . ?
C6 C7 C8 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C6 C5 120.0 . . ?
C7 C6 C11 120.1(4) . . ?
C5 C6 C11 119.9(4) . . ?
C4 C5 C10 120.5(6) . . ?
C6 C5 C4 120.0 . . ?
C6 C5 C10 119.5(6) . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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
N1 C8 C7 C6 -178.2(5) . . . . ?
N3 C9 C8 N1 -0.8(4) . . . . ?
N3 C9 C8 C7 -179.3(4) . . . . ?
C2 N1 C8 C9 1.4(6) . . . . ?
C2 N1 C8 C7 179.7(4) . . . . ?
C2 N3 C9 C4 -179.4(4) . . . . ?
C2 N3 C9 C8 -0.2(5) . . . . ?
C4 C9 C8 N1 178.5(4) . . . . ?
C4 C9 C8 C7 0.0 . . . . ?
C9 N3 C2 N1 1.2(8) . . . . ?
C9 C4 C5 C6 0.0 . . . . ?
C9 C4 C5 C10 178.7(4) . . . . ?
C9 C8 C7 C6 0.0 . . . . ?
C8 N1 C2 N3 -1.6(8) . . . . ?
C8 C7 C6 C5 0.0 . . . . ?
C8 C7 C6 C11 177.1(5) . . . . ?
C7 C6 C5 C4 0.0 . . . . ?
C7 C6 C5 C10 -178.7(4) . . . . ?
C5 C4 C9 N3 179.1(5) . . . . ?
C5 C4 C9 C8 0.0 . . . . ?
C11 C6 C5 C4 -177.1(5) . . . . ?
C11 C6 C5 C10 4.2(5) . . . . ?

_shelx_res_file                  
;
    36_15.res created by SHELXL-2014/7

TITL 36_15 in P1 #1
REM reset to P1 #1
CELL 0.71073 10.036893 7.047701 6.629183 115.3808 94.7109 90.1028
ZERR 2 0.002077 0.000971 0.000958 0.0139 0.0142 0.0137
LATT 1
SFAC C H N O
UNIT 20 28 4 2
ISOR 0.01 0.01 C9 C12 C7 N3 C10 C4 C6 C2 O1 C5 N1 C11 C8

L.S. 44
PLAN  5
BOND
MORE -1
CONF
fmap 2
acta
BOND $H
OMIT 0 0 5
OMIT -1 2 5
OMIT -1 6 3
OMIT -3 2 1
OMIT 1 -1 2
OMIT 2 -3 1
OMIT 7 -2 5
REM <olex2.extras>
REM <HklSrc "%.\\36_15param.hkl">
REM </olex2.extras>

WGHT    0.090000    0.295700
FVAR       3.57522
O1    4    0.578143    0.703055    0.666913    11.00000    0.05961    0.04128 =
         0.05509    0.01837   -0.00439    0.01425
AFIX 147
H1A   2    0.612329    0.817733    0.692224    11.00000   -1.50000
AFIX   0
C12   1    0.491618    0.727551    0.823667    11.00000    0.05555    0.04981 =
         0.06363    0.02827    0.00160    0.00605
AFIX 137
H12A  2    0.536316    0.804609    0.970895    11.00000   -1.50000
H12B  2    0.461318    0.591971    0.807217    11.00000   -1.50000
H12C  2    0.416295    0.803323    0.803263    11.00000   -1.50000
AFIX   0

N1    3    0.699173    0.355981    0.655081    11.00000    0.04428    0.03358 =
         0.04923    0.01782   -0.00979    0.00569
H1    2    0.651550    0.472744    0.655677    11.00000    0.06014
N3    3    0.694756    0.065458    0.715821    11.00000    0.04740    0.03817 =
         0.03710    0.01875   -0.00442    0.00519
C2    1    0.622078    0.203547    0.671448    11.00000    0.04546    0.04369 =
         0.03883    0.02099   -0.00951    0.00201
AFIX  43
H2    2    0.529054    0.197028    0.653547    11.00000   -1.20000
AFIX  66
C4    1    0.944684    0.054548    0.775224    11.00000    0.03325    0.02150 =
         0.03336    0.01550   -0.00348   -0.00263
AFIX  43
H4    2    0.944798   -0.065935    0.799623    11.00000   -1.20000
AFIX  65
C9    1    0.824202    0.133686    0.733058    11.00000    0.02866    0.02781 =
         0.03399    0.01018   -0.00426    0.00029
C8    1    0.824032    0.313763    0.696591    11.00000    0.02927    0.03317 =
         0.03286    0.01457   -0.00532    0.00002
C7    1    0.944343    0.414703    0.702289    11.00000    0.03772    0.03289 =
         0.04066    0.01191   -0.00738    0.00867
AFIX  43
H7    2    0.944229    0.535186    0.677889    11.00000   -1.20000
AFIX  65
C6    1    1.064826    0.335566    0.744454    11.00000    0.03274    0.02878 =
         0.03336    0.01567   -0.00641   -0.01379
C5    1    1.064999    0.155490    0.780922    11.00000    0.02197    0.02635 =
         0.03275    0.01071   -0.00951   -0.00576
AFIX   0
C10   1    1.196920    0.073325    0.831750    11.00000    0.04588    0.05504 =
         0.04013    0.02039   -0.00520    0.01229
AFIX 137
H10A  2    1.182357   -0.065859    0.819967    11.00000   -1.50000
H10B  2    1.233691    0.164243    0.981022    11.00000   -1.50000
H10C  2    1.258240    0.069566    0.726445    11.00000   -1.50000
AFIX   0
C11   1    1.196542    0.439591    0.739757    11.00000    0.04178    0.04051 =
         0.04228    0.01289   -0.00139   -0.00247
AFIX 137
H11A  2    1.248818    0.480966    0.880987    11.00000   -1.50000
H11B  2    1.179104    0.561380    0.713453    11.00000   -1.50000
H11C  2    1.244917    0.342147    0.621862    11.00000   -1.50000
AFIX   0
HKLF 4

REM  36_15 in P1 #1
REM R1 =  0.0612 for     355 Fo > 4sig(Fo)  and  0.0925 for all     520 data
REM    114 parameters refined using     78 restraints

END

WGHT      0.0900      0.2957

REM Highest difference peak  0.187,  deepest hole -0.162,  1-sigma level  0.045
Q1    1   0.3962  0.5767  0.6870  11.00000  0.05    0.19
Q2    1   0.5445  0.9959  0.7864  11.00000  0.05    0.15
Q3    1   0.5255  0.2510  0.7577  11.00000  0.05    0.14
Q4    1   0.6236  0.7346  1.1434  11.00000  0.05    0.14
Q5    1   0.8794  0.5181  0.6112  11.00000  0.05    0.13
;
_shelx_res_checksum              74006
_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_dMBzIm_MeOH_2_19GPa
_database_code_depnum_ccdc_archive 'CCDC 1451570'
_audit_update_record             
;
2016-03-29 deposited with the CCDC.
2016-04-01 downloaded from the CCDC.
;
_audit_creation_date             2016-03-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            '5,6-dimethylbenzimidazole methanol solvate'
_chemical_name_systematic        '5,6-dimethylbenzimidazole methanol solvate'
_chemical_formula_moiety         'C H4 O, C9 H10 N2'
_chemical_formula_sum            'C10 H14 N2 O'
_chemical_formula_weight         178.23
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H14 N2 O1'
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'
O O 0.0106 0.0060 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.007(3)
_cell_length_b                   7.0202(14)
_cell_length_c                   6.5889(12)
_cell_angle_alpha                115.903(19)
_cell_angle_beta                 94.821(18)
_cell_angle_gamma                90.068(19)
_cell_volume                     414.53(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    641
_cell_measurement_temperature    296
_cell_measurement_theta_max      25.3800
_cell_measurement_theta_min      3.2030
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.01010
_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_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             192
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 Data were collected at room temperature and pressure of 2.19(2) GPa
 (2190000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique.
 Pressure was determined by monitoring the shift of the ruby
 R1-fluorescence line.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_Laue_measured_fraction_full 0.262
_diffrn_reflns_Laue_measured_fraction_max 0.235
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            2019
_diffrn_reflns_point_group_measured_fraction_full 0.262
_diffrn_reflns_point_group_measured_fraction_max 0.235
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         3.229
_diffrn_ambient_temperature      296
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1544
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.262
_diffrn_measured_fraction_theta_max 0.235
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    1.00   33.25   0.7500   28.0000
omega____ theta____ kappa____ phi______ frames
    -       15.7462  -53.0000   17.0000 43

#__ type_ start__ end____ width___ exp.time_
  2 omega   29.00   78.50   0.7500   28.0000
omega____ theta____ kappa____ phi______ frames
    -       15.7462 -134.0000 -123.0000 66

#__ type_ start__ end____ width___ exp.time_
  3 omega  -42.00   -6.00   0.7500   28.0000
omega____ theta____ kappa____ phi______ frames
    -       15.7462  -19.0000 -120.0000 48

#__ type_ start__ end____ width___ exp.time_
  4 omega  -15.00   39.00   0.7500   28.0000
omega____ theta____ kappa____ phi______ frames
    -       15.7462  -39.0000 -167.0000 72

#__ type_ start__ end____ width___ exp.time_
  5 omega  -29.00   -2.00   0.7500   28.0000
omega____ theta____ kappa____ phi______ frames
    -       15.7462  114.0000  -44.0000 36

#__ type_ start__ end____ width___ exp.time_
  6 omega  -26.00    1.00   0.7500   28.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.6837   19.0000 -180.0000 36

#__ type_ start__ end____ width___ exp.time_
  7 omega  -37.00    3.50   0.7500   28.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.6837   53.0000  -17.0000 54

#__ type_ start__ end____ width___ exp.time_
  8 omega   -6.00   24.00   0.7500   28.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.6837  -97.0000   35.0000 40

#__ type_ start__ end____ width___ exp.time_
  9 omega  -44.25   42.00   0.7500   28.0000
omega____ theta____ kappa____ phi______ frames
    -       15.7462  -37.0000   30.0000 115

#__ type_ start__ end____ width___ exp.time_
 10 omega  -47.00   -3.50   0.7500   28.0000
omega____ theta____ kappa____ phi______ frames
    -       15.7462  134.0000  123.0000 58

#__ type_ start__ end____ width___ exp.time_
 11 omega  -10.00   34.25   0.7500   28.0000
omega____ theta____ kappa____ phi______ frames
    -       15.7462   37.0000  150.0000 59

#__ type_ start__ end____ width___ exp.time_
 12 omega  -80.00   -3.50   0.7500   28.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.6837  134.0000  -56.0000 102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0342737000
_diffrn_orient_matrix_UB_12      0.0309177000
_diffrn_orient_matrix_UB_13      0.0582974000
_diffrn_orient_matrix_UB_21      0.0181260000
_diffrn_orient_matrix_UB_22      -0.0788279000
_diffrn_orient_matrix_UB_23      0.0362600000
_diffrn_orient_matrix_UB_31      0.1137824000
_diffrn_orient_matrix_UB_32      0.0739519000
_diffrn_orient_matrix_UB_33      0.0188554000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                312
_reflns_number_total             449
_reflns_odcompleteness_completeness 27.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_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       
;
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)'
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         449
_refine_ls_number_restraints     186
_refine_ls_R_factor_all          0.0896
_refine_ls_R_factor_gt           0.0525
_refine_ls_restrained_S_all      0.874
_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)+(0.0910P)²+0.2100P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1324
_refine_ls_wR_factor_ref         0.1587
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(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
 O1, N1, N3, C2, C4, C5, C6, C7, C8, C9, C10, C11, C12
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
O1 \\sim N1 \\sim N3 \\sim C2 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8
\\sim C9 \\sim C10 \\sim C11 \\sim C12: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
Uanis(N1) \\sim Ueq, Uanis(N3) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C2) \\sim
Ueq, Uanis(C8) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C5)
\\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C11) \\sim Ueq,
Uanis(O1) \\sim Ueq, Uanis(C12) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
4.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C4(H4), C7(H7)
4.b Fitted hexagon refined as free rotating group:
 C8(C9,C4,C5,C6,C7)
4.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
4.d Idealised tetrahedral OH refined as rotating group:
 O1(H1A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O1 O 0.5777(12) 0.7042(8) 0.6647(10) 0.039(4) Uani 1 1 d . U . . .
H1A H 0.6150 0.8192 0.6970 0.059 Uiso 1 1 calc GR . . . .
N1 N 0.6973(13) 0.3541(10) 0.6565(10) 0.028(4) Uani 1 1 d . U . . .
H1 H 0.6688 0.4558 0.6272 0.034 Uiso 1 1 calc R . . . .
N3 N 0.6946(13) 0.0653(9) 0.7172(10) 0.026(3) Uani 1 1 d . U . . .
C2 C 0.6209(17) 0.2032(12) 0.6721(13) 0.033(4) Uani 1 1 d . U . . .
H2 H 0.5276 0.1962 0.6536 0.039 Uiso 1 1 calc R . . . .
C8 C 0.8265(7) 0.3160(7) 0.6953(7) 0.025(3) Uani 1 1 d . U . . .
C9 C 0.8266(7) 0.1356(7) 0.7321(7) 0.024(3) Uani 1 1 d G U . . .
C4 C 0.9474(8) 0.0564(6) 0.7750(7) 0.020(3) Uani 1 1 d G U . . .
H4 H 0.9475 -0.0643 0.7996 0.023 Uiso 1 1 calc R . . . .
C5 C 1.0682(7) 0.1577(7) 0.7809(7) 0.022(3) Uani 1 1 d G U . . .
C6 C 1.0680(7) 0.3382(7) 0.7441(8) 0.022(3) Uani 1 1 d G U . . .
C7 C 0.9472(8) 0.4173(6) 0.7012(7) 0.023(3) Uani 1 1 d G U . . .
H7 H 0.9471 0.5380 0.6766 0.028 Uiso 1 1 calc R . . . .
C10 C 1.1960(14) 0.0740(11) 0.8368(12) 0.031(5) Uani 1 1 d . U . . .
H10A H 1.2328 0.1681 0.9873 0.046 Uiso 1 1 calc GR . . . .
H10B H 1.2589 0.0638 0.7306 0.046 Uiso 1 1 calc GR . . . .
H10C H 1.1784 -0.0639 0.8283 0.046 Uiso 1 1 calc GR . . . .
C11 C 1.1969(18) 0.4408(12) 0.7415(14) 0.033(4) Uani 1 1 d . U . . .
H11A H 1.2438 0.3448 0.6181 0.050 Uiso 1 1 calc GR . . . .
H11B H 1.2508 0.4772 0.8819 0.050 Uiso 1 1 calc GR . . . .
H11C H 1.1796 0.5669 0.7228 0.050 Uiso 1 1 calc GR . . . .
C12 C 0.4900(19) 0.7269(14) 0.8265(15) 0.045(5) Uani 1 1 d . U . . .
H12A H 0.4568 0.5895 0.8024 0.068 Uiso 1 1 calc GR . . . .
H12B H 0.4161 0.8092 0.8135 0.068 Uiso 1 1 calc GR . . . .
H12C H 0.5366 0.7974 0.9752 0.068 Uiso 1 1 calc GR . . . .

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
O1 0.044(9) 0.029(3) 0.042(3) 0.013(2) 0.001(5) 0.010(4)
N1 0.028(8) 0.027(3) 0.033(4) 0.017(3) -0.002(5) 0.004(4)
N3 0.028(7) 0.027(3) 0.028(3) 0.015(2) 0.003(5) 0.005(4)
C2 0.029(8) 0.028(4) 0.038(4) 0.013(3) -0.004(5) -0.001(5)
C8 0.020(6) 0.020(3) 0.026(4) 0.005(3) -0.009(5) 0.002(4)
C9 0.023(7) 0.022(3) 0.023(4) 0.008(2) 0.001(5) 0.000(5)
C4 0.025(7) 0.017(3) 0.022(4) 0.013(2) 0.002(5) 0.002(4)
C5 0.021(7) 0.022(4) 0.020(4) 0.007(2) -0.001(5) -0.002(5)
C6 0.022(7) 0.018(4) 0.020(4) 0.004(3) 0.001(5) -0.007(5)
C7 0.027(7) 0.019(4) 0.022(4) 0.008(3) -0.001(5) 0.001(4)
C10 0.024(9) 0.039(4) 0.025(4) 0.012(3) -0.001(5) 0.006(5)
C11 0.030(8) 0.033(4) 0.034(5) 0.011(3) 0.009(6) -0.004(5)
C12 0.042(10) 0.039(5) 0.048(5) 0.014(4) 0.001(6) 0.006(6)

_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
O1 H1A 0.8200 . ?
O1 C12 1.39(3) . ?
N1 H1 0.8600 . ?
N1 C2 1.35(2) . ?
N1 C8 1.346(11) . ?
N3 C2 1.336(7) . ?
N3 C9 1.390(16) . ?
C2 H2 0.9300 . ?
C8 C9 1.3900 . ?
C8 C7 1.3900 . ?
C9 C4 1.3900 . ?
C4 H4 0.9300 . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C5 C10 1.493(8) . ?
C6 C7 1.3900 . ?
C6 C11 1.48(2) . ?
C7 H7 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

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
C12 O1 H1A 109.5 . . ?
C2 N1 H1 126.3 . . ?
C8 N1 H1 126.3 . . ?
C8 N1 C2 107.3(6) . . ?
C2 N3 C9 104.5(11) . . ?
N1 C2 H2 123.8 . . ?
N3 C2 N1 112.4(14) . . ?
N3 C2 H2 123.8 . . ?
N1 C8 C9 107.0(6) . . ?
N1 C8 C7 133.0(6) . . ?
C9 C8 C7 120.0 . . ?
C8 C9 N3 108.8(4) . . ?
C4 C9 N3 131.2(4) . . ?
C4 C9 C8 120.0 . . ?
C9 C4 H4 120.0 . . ?
C9 C4 C5 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C10 118.7(7) . . ?
C6 C5 C4 120.0 . . ?
C6 C5 C10 121.3(7) . . ?
C5 C6 C11 119.9(4) . . ?
C7 C6 C5 120.0 . . ?
C7 C6 C11 120.1(4) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 C8 120.0 . . ?
C6 C7 H7 120.0 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
N1 C8 C9 N3 -0.6(4) . . . . ?
N1 C8 C9 C4 179.4(4) . . . . ?
N1 C8 C7 C6 -179.2(5) . . . . ?
N3 C9 C4 C5 180.0(6) . . . . ?
C2 N1 C8 C9 0.8(6) . . . . ?
C2 N1 C8 C7 -179.9(5) . . . . ?
C2 N3 C9 C8 0.1(6) . . . . ?
C2 N3 C9 C4 -179.8(4) . . . . ?
C8 N1 C2 N3 -0.7(9) . . . . ?
C8 C9 C4 C5 0.0 . . . . ?
C9 N3 C2 N1 0.4(8) . . . . ?
C9 C8 C7 C6 0.0 . . . . ?
C9 C4 C5 C6 0.0 . . . . ?
C9 C4 C5 C10 177.5(4) . . . . ?
C4 C5 C6 C7 0.0 . . . . ?
C4 C5 C6 C11 -177.6(6) . . . . ?
C5 C6 C7 C8 0.0 . . . . ?
C7 C8 C9 N3 -180.0(4) . . . . ?
C7 C8 C9 C4 0.0 . . . . ?
C10 C5 C6 C7 -177.5(4) . . . . ?
C10 C5 C6 C11 5.0(6) . . . . ?
C11 C6 C7 C8 177.6(6) . . . . ?

_shelx_res_file                  
;
    35.res created by SHELXL-2014/7

TITL 35 in P-1 #2
REM reset to P-1 #2
CELL 0.71073 10.00694 7.020249 6.588892 115.9034 94.8212 90.0683
ZERR 2 0.002543 0.00143 0.001203 0.019 0.0178 0.0185
LATT 1
SFAC C H N O
UNIT 20 28 4 2
DELU O1 > C2 C4 > C7 C8 C9 C10 > C12
SIMU O1 > C2 C4 > C7 C8 C9 C10 > C12
ISOR 0.01 0.01 N1 N3 C9 C2 C8 C4 C7 C5 C6 C10 C11 O1 C12

L.S. 44
PLAN  5
BOND
MORE -1
CONF
fmap 2
acta 52
BOND $H
OMIT 5 -6 4
OMIT -2 5 1
REM <olex2.extras>
REM <HklSrc "%.\\35par.hkl">
REM </olex2.extras>

WGHT    0.091000    0.210000
FVAR       3.60854
O1    4    0.577667    0.704250    0.664683    11.00000    0.04372    0.02880 =
         0.04172    0.01285    0.00131    0.00960
AFIX 147
H1A   2    0.615020    0.819225    0.696953    11.00000   -1.50000
AFIX   0
N1    3    0.697331    0.354114    0.656495    11.00000    0.02829    0.02712 =
         0.03283    0.01652   -0.00180    0.00373
AFIX  43
H1    2    0.668767    0.455752    0.627204    11.00000   -1.20000
AFIX   0
N3    3    0.694567    0.065264    0.717161    11.00000    0.02762    0.02722 =
         0.02785    0.01521    0.00349    0.00463
C2    1    0.620949    0.203248    0.672105    11.00000    0.02899    0.02809 =
         0.03843    0.01328   -0.00395   -0.00077
AFIX  43
H2    2    0.527627    0.196169    0.653587    11.00000   -1.20000
AFIX  66
C8    1    0.826455    0.315987    0.695264    11.00000    0.01954    0.02032 =
         0.02635    0.00530   -0.00944    0.00217
C9    1    0.826593    0.135560    0.732123    11.00000    0.02333    0.02219 =
         0.02341    0.00808    0.00123   -0.00014
C4    1    0.947448    0.056433    0.774960    11.00000    0.02512    0.01692 =
         0.02178    0.01327    0.00249    0.00193
AFIX  43
H4    2    0.947540   -0.064285    0.799622    11.00000   -1.20000
AFIX  65
C5    1    1.068167    0.157731    0.780937    11.00000    0.02137    0.02188 =
         0.02047    0.00660   -0.00111   -0.00164
C6    1    1.068031    0.338158    0.744078    11.00000    0.02185    0.01808 =
         0.02042    0.00369    0.00078   -0.00711
C7    1    0.947176    0.417288    0.701241    11.00000    0.02689    0.01939 =
         0.02231    0.00850   -0.00075    0.00061
AFIX  43
H7    2    0.947085    0.538006    0.676579    11.00000   -1.20000
AFIX   0
C10   1    1.195971    0.073969    0.836760    11.00000    0.02449    0.03902 =
         0.02544    0.01215   -0.00110    0.00606
AFIX 137
H10A  2    1.232830    0.168107    0.987274    11.00000   -1.50000
H10B  2    1.258882    0.063813    0.730561    11.00000   -1.50000
H10C  2    1.178393   -0.063880    0.828346    11.00000   -1.50000
AFIX   0
C11   1    1.196899    0.440807    0.741463    11.00000    0.02999    0.03309 =
         0.03351    0.01100    0.00902   -0.00404
AFIX 137
H11A  2    1.243807    0.344830    0.618072    11.00000   -1.50000
H11B  2    1.250817    0.477157    0.881870    11.00000   -1.50000
H11C  2    1.179576    0.566949    0.722753    11.00000   -1.50000
AFIX   0
C12   1    0.489996    0.726862    0.826509    11.00000    0.04247    0.03926 =
         0.04817    0.01391    0.00138    0.00612
AFIX 137
H12A  2    0.456808    0.589517    0.802358    11.00000   -1.50000
H12B  2    0.416138    0.809212    0.813467    11.00000   -1.50000
H12C  2    0.536638    0.797437    0.975196    11.00000   -1.50000
AFIX   0
HKLF 4

REM  35 in P-1 #2
REM R1 =  0.0525 for     312 Fo > 4sig(Fo)  and  0.0896 for all     449 data
REM    110 parameters refined using    186 restraints

END

WGHT      0.0908      0.2092

REM Highest difference peak  0.163,  deepest hole -0.147,  1-sigma level  0.044
Q1    1   0.5771  0.6841  1.1364  11.00000  0.05    0.16
Q2    1   0.6498  0.5911  0.5646  11.00000  0.05    0.15
Q3    1   0.5596  0.6206  0.9710  11.00000  0.05    0.15
Q4    1   1.0255 -0.1091  0.6730  11.00000  0.05    0.14
Q5    1   1.3441 -0.1079  0.6470  11.00000  0.05    0.13
;
_shelx_res_checksum              63642
_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_dMBzIm_MeOH_2_31GPa
_database_code_depnum_ccdc_archive 'CCDC 1451571'
_audit_update_record             
;
2016-03-29 deposited with the CCDC.
2016-04-01 downloaded from the CCDC.
;
_audit_creation_date             2016-03-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            '5,6-dimethylbenzimidazole methanol solvate'
_chemical_name_systematic        '5,6-dimethylbenzimidazole methanol solvate'
_chemical_formula_moiety         'C H4 O, C9 H10 N2'
_chemical_formula_sum            'C10 H14 N2 O'
_chemical_formula_weight         178.23
_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 0.0033 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'
O O 0.0106 0.0060 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.027(10)
_cell_length_b                   7.0054(13)
_cell_length_c                   6.5581(12)
_cell_angle_alpha                116.173(19)
_cell_angle_beta                 94.86(3)
_cell_angle_gamma                90.02(4)
_cell_volume                     411.6(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    572
_cell_measurement_temperature    296
_cell_measurement_theta_max      26.6590
_cell_measurement_theta_min      3.2190
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41626
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             192
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 Data were collected at room temperature and pressure of 2.31(2) GPa
 (2310000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique.
 Pressure was determined by monitoring the shift of the ruby
 R1-fluorescence line.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1078
_diffrn_reflns_av_unetI/netI     0.0653
_diffrn_reflns_Laue_measured_fraction_full 0.241
_diffrn_reflns_Laue_measured_fraction_max 0.213
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            1828
_diffrn_reflns_point_group_measured_fraction_full 0.241
_diffrn_reflns_point_group_measured_fraction_max 0.213
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.868
_diffrn_reflns_theta_min         3.243
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measured_fraction_theta_full 0.241
_diffrn_measured_fraction_theta_max 0.213
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 phi    -35.00   19.75   0.7500   30.0000
omega____ theta____ kappa____ phi______ frames
   0.0000  -30.0000    0.0000     -     73

#__ type_ start__ end____ width___ exp.time_
  2 phi    140.00  200.00   0.7500   30.0000
omega____ theta____ kappa____ phi______ frames
   0.0000  -30.0000    0.0000     -     80

#__ type_ start__ end____ width___ exp.time_
  3 phi    160.00  217.00   0.7500   30.0000
omega____ theta____ kappa____ phi______ frames
   0.0000   30.0000    0.0000     -     76

#__ type_ start__ end____ width___ exp.time_
  4 phi    -20.00   34.75   0.7500   30.0000
omega____ theta____ kappa____ phi______ frames
   0.0000   30.0000    0.0000     -     73

#__ type_ start__ end____ width___ exp.time_
  5 omega  -24.00   24.00   0.7500   30.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   39.4600  -12.9000 64

#__ type_ start__ end____ width___ exp.time_
  6 omega  -24.00   24.00   0.7500   30.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   39.4600  167.1000 64

#__ type_ start__ end____ width___ exp.time_
  7 omega  -50.00   10.00   0.7500   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000   39.4600  167.1000 80

#__ type_ start__ end____ width___ exp.time_
  8 omega  -50.00   10.00   0.7500   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000   39.4600  -12.9000 80

#__ type_ start__ end____ width___ exp.time_
  9 omega  -64.00   -8.50   0.7500   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000   81.4000  -28.9000 74

#__ type_ start__ end____ width___ exp.time_
 10 omega  -64.00   -8.50   0.7500   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000   81.4000  151.1000 74

#__ type_ start__ end____ width___ exp.time_
 11 omega  -19.00    8.00   0.7500   30.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   81.4000  151.1000 36

#__ type_ start__ end____ width___ exp.time_
 12 omega  -19.00    8.00   0.7500   30.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   81.4000  -28.9000 36

#__ type_ start__ end____ width___ exp.time_
 13 omega  -43.00  -21.25   0.7500   30.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  134.6000  -56.9000 29

#__ type_ start__ end____ width___ exp.time_
 14 omega  -43.00  -21.25   0.7500   30.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  134.6000  123.1000 29

#__ type_ start__ end____ width___ exp.time_
 15 omega  -90.00  -36.00   0.7500   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000  134.6000  123.1000 72

#__ type_ start__ end____ width___ exp.time_
 16 omega  -90.00  -36.00   0.7500   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000  134.6000  -56.9000 72
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω and π scans'
_diffrn_orient_matrix_UB_11      -0.0685872000
_diffrn_orient_matrix_UB_12      0.0134739000
_diffrn_orient_matrix_UB_13      0.0198190000
_diffrn_orient_matrix_UB_21      0.0095557000
_diffrn_orient_matrix_UB_22      -0.0415404000
_diffrn_orient_matrix_UB_23      0.0809182000
_diffrn_orient_matrix_UB_31      0.0159417000
_diffrn_orient_matrix_UB_32      0.1041327000
_diffrn_orient_matrix_UB_33      0.0878292000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                277
_reflns_number_total             419
_reflns_odcompleteness_completeness 21.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.81
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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)'
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         419
_refine_ls_number_restraints     186
_refine_ls_R_factor_all          0.1133
_refine_ls_R_factor_gt           0.0757
_refine_ls_restrained_S_all      0.915
_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)+(0.1597P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1960
_refine_ls_wR_factor_ref         0.2366
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(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
 O1, C12, 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
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
Uanis(C12) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(C8) \\sim
Ueq, Uanis(N3) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C6)
\\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C11) \\sim Ueq,
Uanis(C10) \\sim Ueq, Uanis(O1) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
4.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C4(H4), C7(H7)
4.b Fitted hexagon refined as free rotating group:
 C8(C9,C4,C5,C6,C7)
4.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
4.d Idealised tetrahedral OH refined as rotating group:
 O1(H1A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O1 O 0.5765(15) 0.7046(8) 0.6653(10) 0.036(4) Uani 1 1 d . U . . .
H1A H 0.6090 0.8221 0.6937 0.054 Uiso 1 1 calc GR . . . .
C12 C 0.491(3) 0.7250(13) 0.8288(15) 0.043(5) Uani 1 1 d . U . . .
H12A H 0.5394 0.7897 0.9775 0.065 Uiso 1 1 calc GR . . . .
H12B H 0.4557 0.5868 0.7992 0.065 Uiso 1 1 calc GR . . . .
H12C H 0.4185 0.8125 0.8229 0.065 Uiso 1 1 calc GR . . . .
N1 N 0.696(2) 0.3541(11) 0.6538(12) 0.034(4) Uani 1 1 d . U . . .
H1 H 0.6664 0.4551 0.6237 0.041 Uiso 1 1 calc R . . . .
N3 N 0.6967(19) 0.0649(10) 0.7138(11) 0.027(3) Uani 1 1 d . U . . .
C2 C 0.622(2) 0.2032(11) 0.6699(12) 0.032(4) Uani 1 1 d . U . . .
H2 H 0.5284 0.1952 0.6526 0.039 Uiso 1 1 calc R . . . .
C8 C 0.8267(12) 0.3176(8) 0.6941(9) 0.026(3) Uani 1 1 d . U . . .
C9 C 0.8254(12) 0.1383(8) 0.7335(9) 0.022(3) Uani 1 1 d G U . . .
C4 C 0.9453(12) 0.0577(6) 0.7773(8) 0.024(3) Uani 1 1 d G U . . .
H4 H 0.9445 -0.0623 0.8037 0.029 Uiso 1 1 calc R . . . .
C5 C 1.0665(12) 0.1564(8) 0.7817(8) 0.028(3) Uani 1 1 d G U . . .
C6 C 1.0678(12) 0.3357(8) 0.7422(9) 0.030(3) Uani 1 1 d G U . . .
C7 C 0.9479(12) 0.4163(6) 0.6984(8) 0.027(3) Uani 1 1 d G U . . .
H7 H 0.9487 0.5362 0.6720 0.032 Uiso 1 1 calc R . . . .
C10 C 1.195(2) 0.0758(12) 0.8385(14) 0.035(4) Uani 1 1 d . U . . .
H10A H 1.2595 0.0743 0.7372 0.053 Uiso 1 1 calc GR . . . .
H10B H 1.1802 -0.0660 0.8216 0.053 Uiso 1 1 calc GR . . . .
H10C H 1.2290 0.1672 0.9931 0.053 Uiso 1 1 calc GR . . . .
C11 C 1.194(3) 0.4372(13) 0.7404(14) 0.034(4) Uani 1 1 d . U . . .
H11A H 1.2334 0.3516 0.6019 0.052 Uiso 1 1 calc GR . . . .
H11B H 1.2537 0.4514 0.8690 0.052 Uiso 1 1 calc GR . . . .
H11C H 1.1778 0.5755 0.7489 0.052 Uiso 1 1 calc GR . . . .

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
O1 0.039(12) 0.034(3) 0.043(3) 0.025(3) 0.001(5) 0.005(5)
C12 0.042(13) 0.044(5) 0.048(5) 0.025(4) 0.003(7) 0.009(7)
N1 0.036(9) 0.042(4) 0.038(4) 0.031(3) 0.005(6) 0.013(6)
N3 0.029(9) 0.029(3) 0.025(3) 0.015(3) 0.002(6) 0.002(5)
C2 0.032(9) 0.041(4) 0.030(4) 0.023(4) 0.000(7) 0.004(6)
C8 0.032(8) 0.023(3) 0.026(4) 0.014(3) 0.002(7) 0.003(6)
C9 0.027(8) 0.018(4) 0.022(4) 0.009(3) 0.000(7) -0.001(6)
C4 0.030(8) 0.027(4) 0.019(3) 0.014(3) -0.001(7) 0.005(6)
C5 0.030(8) 0.030(4) 0.027(4) 0.015(3) -0.004(7) 0.004(6)
C6 0.032(8) 0.038(4) 0.025(4) 0.019(3) 0.006(7) 0.005(6)
C7 0.030(8) 0.025(3) 0.026(4) 0.013(3) -0.005(7) 0.002(6)
C10 0.030(10) 0.043(4) 0.038(4) 0.023(4) -0.003(7) 0.000(7)
C11 0.033(9) 0.047(4) 0.029(4) 0.021(4) 0.008(7) 0.005(7)

_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
O1 H1A 0.8200 . ?
O1 C12 1.39(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
N1 H1 0.8600 . ?
N1 C2 1.339(18) . ?
N1 C8 1.36(2) . ?
N3 C2 1.341(17) . ?
N3 C9 1.36(2) . ?
C2 H2 0.9300 . ?
C8 C9 1.3900 . ?
C8 C7 1.3900 . ?
C9 C4 1.3900 . ?
C4 H4 0.9300 . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C5 C10 1.49(2) . ?
C6 C7 1.3900 . ?
C6 C11 1.45(2) . ?
C7 H7 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

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
C12 O1 H1A 109.5 . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C2 N1 H1 126.4 . . ?
C2 N1 C8 107.2(11) . . ?
C8 N1 H1 126.4 . . ?
C2 N3 C9 104.7(9) . . ?
N1 C2 N3 112.4(19) . . ?
N1 C2 H2 123.8 . . ?
N3 C2 H2 123.8 . . ?
N1 C8 C9 105.9(5) . . ?
N1 C8 C7 134.0(5) . . ?
C9 C8 C7 120.0 . . ?
N3 C9 C8 109.8(6) . . ?
N3 C9 C4 130.1(6) . . ?
C4 C9 C8 120.0 . . ?
C9 C4 H4 120.0 . . ?
C5 C4 C9 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 C10 120.1(7) . . ?
C6 C5 C10 119.8(6) . . ?
C5 C6 C11 120.6(7) . . ?
C7 C6 C5 120.0 . . ?
C7 C6 C11 119.4(7) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 C8 120.0 . . ?
C6 C7 H7 120.0 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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
N1 C8 C9 N3 1.0(6) . . . . ?
N1 C8 C9 C4 179.1(6) . . . . ?
N1 C8 C7 C6 -178.8(8) . . . . ?
N3 C9 C4 C5 177.6(7) . . . . ?
C2 N1 C8 C9 0.2(8) . . . . ?
C2 N1 C8 C7 179.1(5) . . . . ?
C2 N3 C9 C8 -1.8(7) . . . . ?
C2 N3 C9 C4 -179.7(5) . . . . ?
C8 N1 C2 N3 -1.4(11) . . . . ?
C8 C9 C4 C5 0.0 . . . . ?
C9 N3 C2 N1 2.0(10) . . . . ?
C9 C8 C7 C6 0.0 . . . . ?
C9 C4 C5 C6 0.0 . . . . ?
C9 C4 C5 C10 177.4(6) . . . . ?
C4 C5 C6 C7 0.0 . . . . ?
C4 C5 C6 C11 -178.4(6) . . . . ?
C5 C6 C7 C8 0.0 . . . . ?
C7 C8 C9 N3 -178.1(6) . . . . ?
C7 C8 C9 C4 0.0 . . . . ?
C10 C5 C6 C7 -177.4(6) . . . . ?
C10 C5 C6 C11 4.2(8) . . . . ?
C11 C6 C7 C8 178.4(6) . . . . ?

_shelx_res_file                  
;
    34parok.res created by SHELXL-2014/7

TITL 34parok_a.res in P1
REM Old TITL 34 parok in P-1 #2
REM SHELXT solution in P1
REM R1 0.392, Rweak 0.029, Alpha 0.000, Orientation as input
REM Flack x = 0.139 ( 3.741 ) from Parsons' quotients
REM Formula found by SHELXT: C16 N3 O4
CELL 0.71073 10.026569 7.005354 6.558101 116.1727 94.8619 90.0224
ZERR 2 0.009841 0.00134 0.001153 0.0191 0.0342 0.0379
LATT 1
SFAC C H N O
UNIT 20 28 4 2
DELU O1 C12 N1 N3 C2 C4 > C7 C8 C9 C10 C11
SIMU
ISOR 0.01 0.01 C12 C2 N1 C8 N3 C7 C9 C6 C4 C5 C11 C10 O1

L.S. 44
PLAN  5
BOND $H
LIST 6
MORE -1
CONF
fmap 2
acta 52
OMIT 1 -2 4
OMIT 2 1 1
OMIT 2 0 3
OMIT 3 3 2
OMIT 2 4 1
OMIT 1 -7 3
OMIT 3 2 2
OMIT -1 1 2
OMIT 2 6 1
OMIT 1 4 1
OMIT 2 6 0
OMIT 1 6 1
OMIT 2 -2 4
REM <olex2.extras>
REM <HklSrc "%.\\34%20parok.hkl">
REM </olex2.extras>

WGHT    0.159700
FVAR       1.37314
O1    4    0.576503    0.704606    0.665273    11.00000    0.03920    0.03387 =
         0.04320    0.02505    0.00148    0.00533
AFIX 147
H1A   2    0.609015    0.822069    0.693658    11.00000   -1.50000
AFIX   0
C12   1    0.490927    0.724960    0.828831    11.00000    0.04244    0.04399 =
         0.04794    0.02456    0.00337    0.00940
AFIX 137
H12A  2    0.539392    0.789666    0.977473    11.00000   -1.50000
H12B  2    0.455722    0.586780    0.799213    11.00000   -1.50000
H12C  2    0.418504    0.812506    0.822879    11.00000   -1.50000
AFIX   0

N1    3    0.695800    0.354070    0.653800    11.00000    0.03573    0.04226 =
         0.03833    0.03119    0.00451    0.01297
AFIX  43
H1    2    0.666425    0.455059    0.623720    11.00000   -1.20000
AFIX   0
N3    3    0.696714    0.064928    0.713750    11.00000    0.02881    0.02875 =
         0.02528    0.01457    0.00234    0.00241
C2    1    0.621548    0.203195    0.669873    11.00000    0.03245    0.04095 =
         0.03029    0.02252    0.00049    0.00377
AFIX  43
H2    2    0.528387    0.195204    0.652565    11.00000   -1.20000
AFIX  66
C8    1    0.826676    0.317551    0.694059    11.00000    0.03245    0.02338 =
         0.02597    0.01427    0.00179    0.00277
C9    1    0.825402    0.138250    0.733516    11.00000    0.02660    0.01845 =
         0.02172    0.00933   -0.00025   -0.00067
C4    1    0.945331    0.057681    0.777325    11.00000    0.02957    0.02671 =
         0.01875    0.01365   -0.00135    0.00517
AFIX  43
H4    2    0.944478   -0.062284    0.803724    11.00000   -1.20000
AFIX  65
C5    1    1.066535    0.156411    0.781679    11.00000    0.03011    0.02954 =
         0.02657    0.01543   -0.00440    0.00382
C6    1    1.067811    0.335711    0.742222    11.00000    0.03193    0.03837 =
         0.02494    0.01929    0.00573    0.00485
C7    1    0.947883    0.416284    0.698412    11.00000    0.03028    0.02497 =
         0.02635    0.01339   -0.00509    0.00210
AFIX  43
H7    2    0.948737    0.536248    0.672013    11.00000   -1.20000
AFIX   0
C10   1    1.195295    0.075777    0.838473    11.00000    0.02969    0.04276 =
         0.03825    0.02328   -0.00274    0.00021
AFIX 137
H10A  2    1.259459    0.074287    0.737181    11.00000   -1.50000
H10B  2    1.180228   -0.065988    0.821635    11.00000   -1.50000
H10C  2    1.228988    0.167185    0.993119    11.00000   -1.50000
AFIX   0
C11   1    1.193880    0.437170    0.740356    11.00000    0.03344    0.04655 =
         0.02880    0.02082    0.00836    0.00538
AFIX 137
H11A  2    1.233382    0.351626    0.601901    11.00000   -1.50000
H11B  2    1.253725    0.451406    0.868993    11.00000   -1.50000
H11C  2    1.177798    0.575488    0.748944    11.00000   -1.50000
AFIX   0
HKLF 4

REM  34parok_a.res in P1
REM R1 =  0.0757 for     277 Fo > 4sig(Fo)  and  0.1133 for all     419 data
REM    110 parameters refined using    186 restraints

END

WGHT      0.1597      0.0000

REM Highest difference peak  0.189,  deepest hole -0.216,  1-sigma level  0.060
Q1    1   1.2919  0.1784  1.0776  11.00000  0.05    0.19
Q2    1   0.5371  0.9221  1.0848  11.00000  0.05    0.19
Q3    1   1.0000  0.0000  1.0000  10.50000  0.05    0.18
Q4    1   0.4339  0.5472  0.9416  11.00000  0.05    0.16
Q5    1   1.3079  0.3590  0.9998  11.00000  0.05    0.16
;
_shelx_res_checksum              51538
_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
