# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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. 
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data_dMBzIm_0.11GPa
_database_code_depnum_ccdc_archive 'CCDC 1050857'
_audit_update_record             
;
2015-05-28 deposited with the CCDC.
2015-06-01 downloaded from the CCDC.
;
_audit_creation_date             2015-05-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-4
_chemical_name_common            '5,6-dimethylbenzimidazole phase alpha'
_chemical_name_systematic        
;
 5,6-dimethylbenzimidazole phase alpha
;
_chemical_formula_moiety         '0.5(C18 H20 N4)'
_chemical_formula_sum            'C9 H10 N2'
_chemical_formula_weight         146.19
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C9 H10 N2 '
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_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                   6.5122(6)
_cell_length_b                   27.61(2)
_cell_length_c                   14.0669(13)
_cell_angle_alpha                90
_cell_angle_beta                 102.550(9)
_cell_angle_gamma                90
_cell_volume                     2469(2)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    1434
_cell_measurement_temperature    296
_cell_measurement_theta_max      24.3420
_cell_measurement_theta_min      3.2220
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.16908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    ?
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_special_details           
;
 Data were collected at room temperature and pressure of 0.11(2) GPa
 (110000 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  0.1493
_diffrn_reflns_av_unetI/netI     0.1347
_diffrn_reflns_Laue_measured_fraction_full 0.351
_diffrn_reflns_Laue_measured_fraction_max 0.304
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15179
_diffrn_reflns_point_group_measured_fraction_full 0.351
_diffrn_reflns_point_group_measured_fraction_max 0.304
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.461
_diffrn_reflns_theta_min         2.967
_diffrn_ambient_temperature      296
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1544
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.351
_diffrn_measured_fraction_theta_max 0.304
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 phi    -35.00   19.60   0.7000   31.0000
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   31.0000
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   31.0000
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   31.0000
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   31.0000
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   31.0000
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   31.0000
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   31.0000
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   31.0000
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   31.0000
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   31.0000
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   31.0000
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   31.0000
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   31.0000
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   31.0000
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   31.0000
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      -0.0171815000
_diffrn_orient_matrix_UB_12      -0.0252176000
_diffrn_orient_matrix_UB_13      0.0010834000
_diffrn_orient_matrix_UB_21      0.0538939000
_diffrn_orient_matrix_UB_22      -0.0006508000
_diffrn_orient_matrix_UB_23      0.0496973000
_diffrn_orient_matrix_UB_31      -0.0964747000
_diffrn_orient_matrix_UB_32      0.0041763000
_diffrn_orient_matrix_UB_33      0.0145072000
_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                748
_reflns_number_total             1896
_reflns_odcompleteness_completeness 31.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.40
_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, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.187
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         1896
_refine_ls_number_restraints     501
_refine_ls_R_factor_all          0.2578
_refine_ls_R_factor_gt           0.1192
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3185
_refine_ls_wR_factor_ref         0.4008
_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
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 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 0.001 and
sigma for terminal atoms of 0.002
4. Others
 Fixed Sof: H1(0.5) H3(0.5) H4A(0.5) H5(0.5) H6(0.5) H7A(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), C2(H2), C4(H4), C7(H7), N4(H4A), N5(H5), C12(H12), C13(H13),
 C16(H16), N6(H6), N7(H7A), C21(H21), C22(H22), C25(H25)
5.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C)
;
_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
N1 N 0.1721(9) 0.1206(6) -0.0769(5) 0.062(2) Uani 1 1 d . U . . .
H1 H 0.1166 0.1257 -0.1374 0.075 Uiso 0.5 1 calc R . P . .
N3 N 0.2128(10) 0.0920(6) 0.0730(5) 0.073(2) Uani 1 1 d . U . . .
H3 H 0.1889 0.0768 0.1228 0.087 Uiso 0.5 1 calc R . P . .
C2 C 0.0916(13) 0.0932(8) -0.0149(6) 0.067(2) Uani 1 1 d . U . . .
H2 H -0.0359 0.0769 -0.0323 0.080 Uiso 1 1 calc R . . . .
C4 C 0.5544(12) 0.1345(8) 0.1438(6) 0.071(3) Uani 1 1 d . U . . .
H4 H 0.5693 0.1242 0.2079 0.085 Uiso 1 1 calc R . . . .
C5 C 0.7020(13) 0.1654(9) 0.1174(6) 0.076(3) Uani 1 1 d . U . . .
C6 C 0.6813(13) 0.1813(8) 0.0213(6) 0.073(3) Uani 1 1 d . U . . .
C7 C 0.5067(12) 0.1675(8) -0.0493(6) 0.070(2) Uani 1 1 d . U . . .
H7 H 0.4922 0.1782 -0.1131 0.084 Uiso 1 1 calc R . . . .
C8 C 0.3597(11) 0.1390(8) -0.0256(5) 0.056(2) Uani 1 1 d . U . . .
C9 C 0.3789(11) 0.1190(7) 0.0695(5) 0.056(2) Uani 1 1 d . U . . .
C10 C 0.8452(13) 0.2154(9) -0.0032(7) 0.095(3) Uani 1 1 d . U . . .
H10A H 0.9716 0.1976 -0.0040 0.143 Uiso 1 1 calc GR . . . .
H10B H 0.8754 0.2405 0.0451 0.143 Uiso 1 1 calc GR . . . .
H10C H 0.7924 0.2296 -0.0660 0.143 Uiso 1 1 calc GR . . . .
C11 C 0.8912(13) 0.1829(10) 0.1972(8) 0.103(3) Uani 1 1 d . U . . .
H11A H 1.0199 0.1764 0.1767 0.155 Uiso 1 1 calc GR . . . .
H11B H 0.8919 0.1659 0.2568 0.155 Uiso 1 1 calc GR . . . .
H11C H 0.8789 0.2170 0.2072 0.155 Uiso 1 1 calc GR . . . .
N4 N 0.0807(10) 0.0616(6) 0.2438(5) 0.071(2) Uani 1 1 d . U . . .
H4A H 0.1242 0.0668 0.1912 0.085 Uiso 0.5 1 calc R . P . .
N5 N 0.0674(10) 0.0649(6) 0.3995(5) 0.072(2) Uani 1 1 d . U . . .
H5 H 0.0919 0.0735 0.4596 0.087 Uiso 0.5 1 calc R . P . .
C12 C 0.1788(13) 0.0752(8) 0.3354(6) 0.075(3) Uani 1 1 d . U . . .
H12 H 0.3100 0.0900 0.3506 0.090 Uiso 1 1 calc R . . . .
C13 C -0.2655(12) 0.0174(8) 0.3804(7) 0.075(3) Uani 1 1 d . U . . .
H13 H -0.2767 0.0213 0.4447 0.089 Uiso 1 1 calc R . . . .
C14 C -0.4164(13) -0.0083(9) 0.3155(6) 0.081(3) Uani 1 1 d . U . . .
C15 C -0.4123(14) -0.0083(9) 0.2151(7) 0.082(3) Uani 1 1 d . U . . .
C16 C -0.2503(12) 0.0147(8) 0.1815(7) 0.074(3) Uani 1 1 d . U . . .
H16 H -0.2452 0.0141 0.1160 0.088 Uiso 1 1 calc R . . . .
C17 C -0.0950(12) 0.0389(8) 0.2509(6) 0.065(2) Uani 1 1 d . U . . .
C18 C -0.1012(12) 0.0367(8) 0.3490(6) 0.062(2) Uani 1 1 d . U . . .
C19 C -0.5845(14) -0.0372(10) 0.1418(8) 0.099(3) Uani 1 1 d . U . . .
H19A H -0.6185 -0.0203 0.0808 0.149 Uiso 1 1 calc GR . . . .
H19B H -0.7085 -0.0402 0.1679 0.149 Uiso 1 1 calc GR . . . .
H19C H -0.5320 -0.0689 0.1319 0.149 Uiso 1 1 calc GR . . . .
C20 C -0.5862(14) -0.0377(10) 0.3512(8) 0.100(3) Uani 1 1 d . U . . .
H20A H -0.7050 -0.0173 0.3524 0.149 Uiso 1 1 calc GR . . . .
H20B H -0.5294 -0.0497 0.4156 0.149 Uiso 1 1 calc GR . . . .
H20C H -0.6299 -0.0644 0.3079 0.149 Uiso 1 1 calc GR . . . .
N6 N -0.0014(9) 0.1116(6) 0.5694(5) 0.068(2) Uani 1 1 d . U . . .
H6 H 0.0357 0.0973 0.5215 0.081 Uiso 0.5 1 calc R . P . .
N7 N 0.0065(9) 0.1334(6) 0.7216(5) 0.065(2) Uani 1 1 d . U . . .
H7A H 0.0432 0.1345 0.7841 0.078 Uiso 0.5 1 calc R . P . .
C21 C 0.1002(13) 0.1116(8) 0.6636(6) 0.072(3) Uani 1 1 d . U . . .
H21 H 0.2300 0.0966 0.6848 0.086 Uiso 1 1 calc R . . . .
C22 C -0.3241(12) 0.1849(8) 0.6834(6) 0.069(2) Uani 1 1 d . U . . .
H22 H -0.3176 0.1961 0.7464 0.083 Uiso 1 1 calc R . . . .
C23 C -0.4872(13) 0.1976(9) 0.6089(6) 0.079(3) Uani 1 1 d . U . . .
C24 C -0.4934(14) 0.1837(9) 0.5134(7) 0.086(3) Uani 1 1 d . U . . .
C25 C -0.3373(12) 0.1551(8) 0.4892(6) 0.071(2) Uani 1 1 d . U . . .
H25 H -0.3400 0.1469 0.4249 0.086 Uiso 1 1 calc R . . . .
C26 C -0.1731(12) 0.1389(8) 0.5664(6) 0.061(2) Uani 1 1 d . U . . .
C27 C -0.1669(12) 0.1547(8) 0.6627(6) 0.061(2) Uani 1 1 d . U . . .
C28 C -0.6743(14) 0.2010(9) 0.4302(8) 0.102(3) Uani 1 1 d . U . . .
H28A H -0.6778 0.2358 0.4291 0.153 Uiso 1 1 calc GR . . . .
H28B H -0.8057 0.1889 0.4407 0.153 Uiso 1 1 calc GR . . . .
H28C H -0.6518 0.1892 0.3691 0.153 Uiso 1 1 calc GR . . . .
C29 C -0.6575(14) 0.2328(9) 0.6302(7) 0.101(3) Uani 1 1 d . U . . .
H29A H -0.6775 0.2587 0.5836 0.151 Uiso 1 1 calc GR . . . .
H29B H -0.6126 0.2458 0.6946 0.151 Uiso 1 1 calc GR . . . .
H29C H -0.7875 0.2157 0.6254 0.151 Uiso 1 1 calc GR . . . .


_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
N1 H1 0.8600 . ?
N1 C2 1.344(16) . ?
N1 C8 1.374(12) . ?
N3 H3 0.8600 . ?
N3 C2 1.315(9) . ?
N3 C9 1.323(15) . ?
C2 H2 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.395(19) . ?
C4 C9 1.436(13) . ?
C5 C6 1.399(15) . ?
C5 C11 1.552(15) . ?
C6 C7 1.391(12) . ?
C6 C10 1.52(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.337(17) . ?
C8 C9 1.426(14) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
N4 H4A 0.8600 . ?
N4 C12 1.361(12) . ?
N4 C17 1.328(14) . ?
N5 H5 0.8600 . ?
N5 C12 1.305(10) . ?
N5 C18 1.406(16) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.382(18) . ?
C13 C18 1.352(13) . ?
C14 C15 1.419(13) . ?
C14 C20 1.542(19) . ?
C15 C16 1.399(16) . ?
C15 C19 1.57(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.412(17) . ?
C17 C18 1.391(10) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
N6 H6 0.8600 . ?
N6 C21 1.347(9) . ?
N6 C26 1.341(15) . ?
N7 H7A 0.8600 . ?
N7 C21 1.272(15) . ?
N7 C27 1.380(13) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C22 C23 1.366(12) . ?
C22 C27 1.400(18) . ?
C23 C24 1.389(15) . ?
C23 C29 1.55(2) . ?
C24 C25 1.386(19) . ?
C24 C28 1.545(14) . ?
C25 H25 0.9300 . ?
C25 C26 1.421(14) . ?
C26 C27 1.415(13) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 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
C2 N1 H1 126.4 . . ?
C2 N1 C8 107.1(8) . . ?
C8 N1 H1 126.4 . . ?
C2 N3 H3 126.9 . . ?
C2 N3 C9 106.2(10) . . ?
C9 N3 H3 126.9 . . ?
N1 C2 H2 123.7 . . ?
N3 C2 N1 112.7(11) . . ?
N3 C2 H2 123.7 . . ?
C5 C4 H4 120.9 . . ?
C5 C4 C9 118.2(10) . . ?
C9 C4 H4 120.9 . . ?
C4 C5 C6 121.5(11) . . ?
C4 C5 C11 118.8(10) . . ?
C6 C5 C11 119.7(14) . . ?
C5 C6 C10 119.3(10) . . ?
C7 C6 C5 119.7(13) . . ?
C7 C6 C10 120.9(10) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.1(10) . . ?
C8 C7 H7 119.9 . . ?
N1 C8 C9 103.7(11) . . ?
C7 C8 N1 133.6(9) . . ?
C7 C8 C9 122.7(9) . . ?
N3 C9 C4 131.9(9) . . ?
N3 C9 C8 110.3(8) . . ?
C8 C9 C4 117.5(12) . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C12 N4 H4A 126.5 . . ?
C17 N4 H4A 126.5 . . ?
C17 N4 C12 107.1(8) . . ?
C12 N5 H5 127.4 . . ?
C12 N5 C18 105.2(9) . . ?
C18 N5 H5 127.4 . . ?
N4 C12 H12 123.9 . . ?
N5 C12 N4 112.1(10) . . ?
N5 C12 H12 123.9 . . ?
C14 C13 H13 120.5 . . ?
C18 C13 H13 120.5 . . ?
C18 C13 C14 119.1(9) . . ?
C13 C14 C15 119.6(13) . . ?
C13 C14 C20 120.9(9) . . ?
C15 C14 C20 119.6(13) . . ?
C14 C15 C19 119.3(13) . . ?
C16 C15 C14 121.0(12) . . ?
C16 C15 C19 119.6(9) . . ?
C15 C16 H16 121.3 . . ?
C15 C16 C17 117.4(9) . . ?
C17 C16 H16 121.3 . . ?
N4 C17 C16 132.1(8) . . ?
N4 C17 C18 107.9(9) . . ?
C18 C17 C16 119.7(11) . . ?
C13 C18 N5 129.8(8) . . ?
C13 C18 C17 122.5(10) . . ?
C17 C18 N5 106.8(10) . . ?
C15 C19 H19A 109.5 . . ?
C15 C19 H19B 109.5 . . ?
C15 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C14 C20 H20A 109.5 . . ?
C14 C20 H20B 109.5 . . ?
C14 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C21 N6 H6 127.5 . . ?
C26 N6 H6 127.5 . . ?
C26 N6 C21 105.0(9) . . ?
C21 N7 H7A 127.4 . . ?
C21 N7 C27 105.1(8) . . ?
C27 N7 H7A 127.4 . . ?
N6 C21 H21 122.3 . . ?
N7 C21 N6 115.4(10) . . ?
N7 C21 H21 122.3 . . ?
C23 C22 H22 120.8 . . ?
C23 C22 C27 118.3(10) . . ?
C27 C22 H22 120.8 . . ?
C22 C23 C24 121.7(13) . . ?
C22 C23 C29 118.8(11) . . ?
C24 C23 C29 119.2(11) . . ?
C23 C24 C28 120.3(14) . . ?
C25 C24 C23 121.7(11) . . ?
C25 C24 C28 118.0(10) . . ?
C24 C25 H25 121.2 . . ?
C24 C25 C26 117.5(10) . . ?
C26 C25 H25 121.2 . . ?
N6 C26 C25 133.2(9) . . ?
N6 C26 C27 107.1(8) . . ?
C27 C26 C25 119.6(12) . . ?
N7 C27 C22 132.0(8) . . ?
N7 C27 C26 107.0(11) . . ?
C22 C27 C26 120.9(9) . . ?
C24 C28 H28A 109.5 . . ?
C24 C28 H28B 109.5 . . ?
C24 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C23 C29 H29A 109.5 . . ?
C23 C29 H29B 109.5 . . ?
C23 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 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 -1.2(17) . . . . ?
N1 C8 C9 C4 -175.4(13) . . . . ?
C2 N1 C8 C7 179.1(17) . . . . ?
C2 N1 C8 C9 0.9(17) . . . . ?
C2 N3 C9 C4 174.1(17) . . . . ?
C2 N3 C9 C8 1.0(17) . . . . ?
C4 C5 C6 C7 2(3) . . . . ?
C4 C5 C6 C10 179.3(16) . . . . ?
C5 C4 C9 N3 -176.8(16) . . . . ?
C5 C4 C9 C8 -4(2) . . . . ?
C5 C6 C7 C8 0(3) . . . . ?
C6 C7 C8 N1 178.2(18) . . . . ?
C6 C7 C8 C9 -4(2) . . . . ?
C7 C8 C9 N3 -179.6(14) . . . . ?
C7 C8 C9 C4 6(2) . . . . ?
C8 N1 C2 N3 -0.3(19) . . . . ?
C9 N3 C2 N1 -0.4(18) . . . . ?
C9 C4 C5 C6 0(2) . . . . ?
C9 C4 C5 C11 179.3(17) . . . . ?
C10 C6 C7 C8 -177.4(16) . . . . ?
C11 C5 C6 C7 -177.0(17) . . . . ?
C11 C5 C6 C10 0(3) . . . . ?
N4 C17 C18 N5 7.4(19) . . . . ?
N4 C17 C18 C13 177.2(16) . . . . ?
C12 N4 C17 C16 -175.5(19) . . . . ?
C12 N4 C17 C18 -2.4(19) . . . . ?
C12 N5 C18 C13 -178.3(18) . . . . ?
C12 N5 C18 C17 -9.6(18) . . . . ?
C13 C14 C15 C16 4(3) . . . . ?
C13 C14 C15 C19 -179.7(16) . . . . ?
C14 C13 C18 N5 178.3(19) . . . . ?
C14 C13 C18 C17 11(3) . . . . ?
C14 C15 C16 C17 -2(3) . . . . ?
C15 C16 C17 N4 176.2(17) . . . . ?
C15 C16 C17 C18 4(2) . . . . ?
C16 C17 C18 N5 -178.4(15) . . . . ?
C16 C17 C18 C13 -9(3) . . . . ?
C17 N4 C12 N5 -4(2) . . . . ?
C18 N5 C12 N4 9(2) . . . . ?
C18 C13 C14 C15 -9(3) . . . . ?
C18 C13 C14 C20 170.1(16) . . . . ?
C19 C15 C16 C17 -177.9(17) . . . . ?
C20 C14 C15 C16 -174.6(16) . . . . ?
C20 C14 C15 C19 2(3) . . . . ?
N6 C26 C27 N7 -3.6(18) . . . . ?
N6 C26 C27 C22 178.8(15) . . . . ?
C21 N6 C26 C25 176.2(19) . . . . ?
C21 N6 C26 C27 0.1(17) . . . . ?
C21 N7 C27 C22 -177.0(18) . . . . ?
C21 N7 C27 C26 5.7(18) . . . . ?
C22 C23 C24 C25 2(3) . . . . ?
C22 C23 C24 C28 -176.6(17) . . . . ?
C23 C22 C27 N7 -175.0(16) . . . . ?
C23 C22 C27 C26 2(2) . . . . ?
C23 C24 C25 C26 2(3) . . . . ?
C24 C25 C26 N6 -179.8(18) . . . . ?
C24 C25 C26 C27 -4(3) . . . . ?
C25 C26 C27 N7 179.7(14) . . . . ?
C25 C26 C27 C22 2(2) . . . . ?
C26 N6 C21 N7 3.8(19) . . . . ?
C27 N7 C21 N6 -6(2) . . . . ?
C27 C22 C23 C24 -4(3) . . . . ?
C27 C22 C23 C29 -177.4(16) . . . . ?
C28 C24 C25 C26 -179.2(17) . . . . ?
C29 C23 C24 C25 175.3(17) . . . . ?
C29 C23 C24 C28 -3(3) . . . . ?

_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_0.22GPa
_database_code_depnum_ccdc_archive 'CCDC 1050858'
_audit_update_record             
;
2015-05-28 deposited with the CCDC.
2015-06-01 downloaded from the CCDC.
;
_audit_creation_date             2015-05-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-4
_chemical_name_common            '5,6-dimethylbenzimidazole phase alpha'
_chemical_name_systematic        
;
 5,6-dimethylbenzimidazole phase alpha
;
_chemical_formula_moiety         'C9 H10 N2'
_chemical_formula_sum            'C9 H10 N2'
_chemical_formula_weight         146.19
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C9 H10 N2'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_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                   6.4776(7)
_cell_length_b                   27.51(3)
_cell_length_c                   14.0381(15)
_cell_angle_alpha                90
_cell_angle_beta                 102.456(10)
_cell_angle_gamma                90
_cell_volume                     2443(3)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    1697
_cell_measurement_temperature    296
_cell_measurement_theta_max      23.2980
_cell_measurement_theta_min      2.9670
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51859
_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.

Correction for absorption of the diamond-anvil cell and the sample 
 were made using program REDSHABS (Katrusiak, A. (2003) REDSHABS. Adam
 Mickiewicz University Poznań; Katrusiak, A. (2004) Z. Kristallogr.
 219, 461-467).
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    ?
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_special_details           
;
 Data were collected at room temperature and pressure of 0.22(2) GPa
 (220000 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  0.1360
_diffrn_reflns_av_unetI/netI     0.1087
_diffrn_reflns_Laue_measured_fraction_full 0.330
_diffrn_reflns_Laue_measured_fraction_max 0.258
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16405
_diffrn_reflns_point_group_measured_fraction_full 0.330
_diffrn_reflns_point_group_measured_fraction_max 0.258
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.693
_diffrn_reflns_theta_min         2.972
_diffrn_ambient_temperature      296
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3200
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.330
_diffrn_measured_fraction_theta_max 0.258
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 phi    -35.00   19.60   0.7000   30.0000
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   30.0000
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   30.0000
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   30.0000
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   30.0000
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   30.0000
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   30.0000
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   30.0000
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   30.0000
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   30.0000
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   30.0000
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   30.0000
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   30.0000
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   30.0000
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   30.0000
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   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.0000  134.6000  -56.9000 77
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω and π scans'
_diffrn_orient_matrix_UB_11      0.0174858000
_diffrn_orient_matrix_UB_12      -0.0253245000
_diffrn_orient_matrix_UB_13      -0.0011837000
_diffrn_orient_matrix_UB_21      -0.0539775000
_diffrn_orient_matrix_UB_22      -0.0006329000
_diffrn_orient_matrix_UB_23      -0.0497432000
_diffrn_orient_matrix_UB_31      0.0969767000
_diffrn_orient_matrix_UB_32      0.0042519000
_diffrn_orient_matrix_UB_33      -0.0145254000
_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                792
_reflns_number_total             1961
_reflns_odcompleteness_completeness 27.11
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.62
_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, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.197
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         1961
_refine_ls_number_restraints     198
_refine_ls_R_factor_all          0.2476
_refine_ls_R_factor_gt           0.1177
_refine_ls_restrained_S_all      1.148
_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          0.3170
_refine_ls_wR_factor_ref         0.3922
_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
2. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.001 and
sigma for terminal atoms of 0.002
3. Others
 Fixed Sof: H1(0.5) H3(0.5) H4A(0.5) H5(0.5) H6(0.5) H7A(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), C2(H2), C4(H4), C7(H7), N4(H4A), N5(H5), C12(H12), C13(H13),
 C16(H16), N6(H6), N7(H7A), C21(H21), C22(H22), C25(H25)
4.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C)
;
_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
N1 N 0.1744(8) 0.1219(5) -0.0777(4) 0.0604(19) Uani 1 1 d . . . . .
H1 H 0.1181 0.1279 -0.1378 0.072 Uiso 0.5 1 calc R . P . .
N3 N 0.2120(8) 0.0922(6) 0.0724(4) 0.070(2) Uani 1 1 d . . . . .
H3 H 0.1860 0.0772 0.1222 0.084 Uiso 0.5 1 calc R . P . .
C2 C 0.0936(11) 0.0931(7) -0.0164(5) 0.070(2) Uani 1 1 d . . . . .
H2 H -0.0321 0.0759 -0.0352 0.084 Uiso 1 1 calc R . . . .
C4 C 0.5558(10) 0.1345(8) 0.1412(6) 0.068(3) Uani 1 1 d . . . . .
H4 H 0.5708 0.1237 0.2051 0.082 Uiso 1 1 calc R . . . .
C5 C 0.7056(12) 0.1650(8) 0.1180(6) 0.077(3) Uani 1 1 d . . . . .
C6 C 0.6794(12) 0.1810(8) 0.0203(6) 0.079(3) Uani 1 1 d . . . . .
C7 C 0.5070(10) 0.1679(8) -0.0521(6) 0.071(3) Uani 1 1 d . . . . .
H7 H 0.4933 0.1783 -0.1162 0.085 Uiso 1 1 calc R . . . .
C8 C 0.3622(9) 0.1396(7) -0.0258(5) 0.054(2) Uani 1 1 d . . . . .
C9 C 0.3791(10) 0.1192(7) 0.0694(5) 0.053(2) Uani 1 1 d . . . . .
C10 C 0.8436(13) 0.2169(9) -0.0063(7) 0.106(4) Uani 1 1 d . . . . .
H10A H 0.8464 0.2462 0.0313 0.160 Uiso 1 1 calc GR . . . .
H10B H 0.8047 0.2246 -0.0745 0.160 Uiso 1 1 calc GR . . . .
H10C H 0.9811 0.2022 0.0080 0.160 Uiso 1 1 calc GR . . . .
C11 C 0.8960(13) 0.1830(9) 0.1958(8) 0.105(4) Uani 1 1 d . . . . .
H11A H 0.9053 0.2178 0.1923 0.158 Uiso 1 1 calc GR . . . .
H11B H 1.0235 0.1688 0.1842 0.158 Uiso 1 1 calc GR . . . .
H11C H 0.8777 0.1738 0.2594 0.158 Uiso 1 1 calc GR . . . .
N4 N 0.0846(9) 0.0609(6) 0.2431(4) 0.071(2) Uani 1 1 d . . . . .
H4A H 0.1312 0.0654 0.1909 0.085 Uiso 0.5 1 calc R . P . .
N5 N 0.0687(9) 0.0638(6) 0.3991(4) 0.070(2) Uani 1 1 d . . . . .
H5 H 0.0971 0.0716 0.4599 0.083 Uiso 0.5 1 calc R . P . .
C12 C 0.1773(12) 0.0747(8) 0.3336(6) 0.077(3) Uani 1 1 d . . . . .
H12 H 0.3069 0.0906 0.3485 0.092 Uiso 1 1 calc R . . . .
C13 C -0.2650(11) 0.0158(8) 0.3813(6) 0.074(3) Uani 1 1 d . . . . .
H13 H -0.2722 0.0177 0.4467 0.089 Uiso 1 1 calc R . . . .
C14 C -0.4187(12) -0.0084(8) 0.3155(6) 0.076(3) Uani 1 1 d . . . . .
C15 C -0.4126(13) -0.0080(8) 0.2143(7) 0.085(3) Uani 1 1 d . . . . .
C16 C -0.2465(11) 0.0129(8) 0.1822(6) 0.072(3) Uani 1 1 d . . . . .
H16 H -0.2360 0.0099 0.1174 0.087 Uiso 1 1 calc R . . . .
C17 C -0.0922(10) 0.0388(7) 0.2499(5) 0.055(2) Uani 1 1 d . . . . .
C18 C -0.1017(10) 0.0371(7) 0.3496(5) 0.058(2) Uani 1 1 d . . . . .
C19 C -0.5851(14) -0.0377(10) 0.1425(7) 0.106(4) Uani 1 1 d . . . . .
H19A H -0.5283 -0.0687 0.1300 0.159 Uiso 1 1 calc GR . . . .
H19B H -0.6275 -0.0202 0.0823 0.159 Uiso 1 1 calc GR . . . .
H19C H -0.7055 -0.0425 0.1712 0.159 Uiso 1 1 calc GR . . . .
C20 C -0.5831(14) -0.0372(10) 0.3545(7) 0.106(4) Uani 1 1 d . . . . .
H20A H -0.5408 -0.0394 0.4243 0.159 Uiso 1 1 calc GR . . . .
H20B H -0.5949 -0.0692 0.3269 0.159 Uiso 1 1 calc GR . . . .
H20C H -0.7174 -0.0210 0.3371 0.159 Uiso 1 1 calc GR . . . .
N6 N 0.0016(8) 0.1119(6) 0.5694(4) 0.068(2) Uani 1 1 d . . . . .
H6 H 0.0407 0.0978 0.5216 0.082 Uiso 0.5 1 calc R . P . .
N7 N 0.0079(8) 0.1348(6) 0.7204(4) 0.066(2) Uani 1 1 d . . . . .
H7A H 0.0456 0.1372 0.7828 0.079 Uiso 0.5 1 calc R . P . .
C21 C 0.1039(11) 0.1115(8) 0.6645(6) 0.075(3) Uani 1 1 d . . . . .
H21 H 0.2322 0.0957 0.6868 0.091 Uiso 1 1 calc R . . . .
C22 C -0.3240(11) 0.1842(8) 0.6829(6) 0.071(2) Uani 1 1 d . . . . .
H22 H -0.3204 0.1940 0.7467 0.085 Uiso 1 1 calc R . . . .
C23 C -0.4878(12) 0.1986(9) 0.6069(6) 0.082(3) Uani 1 1 d . . . . .
C24 C -0.4947(13) 0.1845(9) 0.5131(6) 0.086(3) Uani 1 1 d . . . . .
C25 C -0.3385(10) 0.1558(8) 0.4879(6) 0.069(2) Uani 1 1 d . . . . .
H25 H -0.3422 0.1481 0.4230 0.083 Uiso 1 1 calc R . . . .
C26 C -0.1691(10) 0.1381(7) 0.5654(5) 0.056(2) Uani 1 1 d . . . . .
C27 C -0.1679(10) 0.1552(7) 0.6615(5) 0.054(2) Uani 1 1 d . . . . .
C28 C -0.6744(14) 0.2011(10) 0.4289(9) 0.117(4) Uani 1 1 d . . . . .
H28A H -0.8064 0.1884 0.4385 0.175 Uiso 1 1 calc GR . . . .
H28B H -0.6484 0.1894 0.3682 0.175 Uiso 1 1 calc GR . . . .
H28C H -0.6805 0.2360 0.4276 0.175 Uiso 1 1 calc GR . . . .
C29 C -0.6581(13) 0.2310(9) 0.6297(8) 0.112(4) Uani 1 1 d . . . . .
H29A H -0.7845 0.2124 0.6271 0.168 Uiso 1 1 calc GR . . . .
H29B H -0.6867 0.2569 0.5827 0.168 Uiso 1 1 calc GR . . . .
H29C H -0.6118 0.2445 0.6938 0.168 Uiso 1 1 calc GR . . . .


_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
N1 H1 0.8600 . ?
N1 C2 1.354(15) . ?
N1 C8 1.366(11) . ?
N3 H3 0.8600 . ?
N3 C2 1.316(9) . ?
N3 C9 1.320(14) . ?
C2 H2 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.375(18) . ?
C4 C9 1.415(11) . ?
C5 C6 1.415(15) . ?
C5 C11 1.543(14) . ?
C6 C7 1.387(12) . ?
C6 C10 1.55(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.330(16) . ?
C8 C9 1.433(13) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
N4 H4A 0.8600 . ?
N4 C12 1.338(11) . ?
N4 C17 1.317(12) . ?
N5 H5 0.8600 . ?
N5 C12 1.308(10) . ?
N5 C18 1.383(15) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.375(16) . ?
C13 C18 1.365(13) . ?
C14 C15 1.430(12) . ?
C14 C20 1.522(19) . ?
C15 C16 1.378(14) . ?
C15 C19 1.564(19) . ?
C16 H16 0.9300 . ?
C16 C17 1.415(16) . ?
C17 C18 1.415(9) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
N6 H6 0.8600 . ?
N6 C21 1.355(9) . ?
N6 C26 1.312(14) . ?
N7 H7A 0.8600 . ?
N7 C21 1.274(14) . ?
N7 C27 1.375(12) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C22 C23 1.391(12) . ?
C22 C27 1.371(17) . ?
C23 C24 1.364(15) . ?
C23 C29 1.51(2) . ?
C24 C25 1.388(19) . ?
C24 C28 1.539(14) . ?
C25 H25 0.9300 . ?
C25 C26 1.452(13) . ?
C26 C27 1.427(12) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 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
C2 N1 H1 126.5 . . ?
C2 N1 C8 107.0(7) . . ?
C8 N1 H1 126.5 . . ?
C2 N3 H3 127.1 . . ?
C2 N3 C9 105.9(9) . . ?
C9 N3 H3 127.1 . . ?
N1 C2 H2 123.6 . . ?
N3 C2 N1 112.8(10) . . ?
N3 C2 H2 123.6 . . ?
C5 C4 H4 119.4 . . ?
C5 C4 C9 121.1(9) . . ?
C9 C4 H4 119.4 . . ?
C4 C5 C6 118.5(9) . . ?
C4 C5 C11 121.7(10) . . ?
C6 C5 C11 119.8(13) . . ?
C5 C6 C10 119.0(10) . . ?
C7 C6 C5 122.6(13) . . ?
C7 C6 C10 118.3(10) . . ?
C6 C7 H7 121.5 . . ?
C8 C7 C6 117.0(9) . . ?
C8 C7 H7 121.5 . . ?
N1 C8 C9 103.7(9) . . ?
C7 C8 N1 131.4(8) . . ?
C7 C8 C9 124.8(7) . . ?
N3 C9 C4 133.4(8) . . ?
N3 C9 C8 110.6(7) . . ?
C4 C9 C8 115.8(11) . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C12 N4 H4A 126.8 . . ?
C17 N4 H4A 126.8 . . ?
C17 N4 C12 106.3(7) . . ?
C12 N5 H5 127.5 . . ?
C12 N5 C18 105.0(8) . . ?
C18 N5 H5 127.5 . . ?
N4 C12 H12 123.1 . . ?
N5 C12 N4 113.8(10) . . ?
N5 C12 H12 123.1 . . ?
C14 C13 H13 120.4 . . ?
C18 C13 H13 120.4 . . ?
C18 C13 C14 119.2(8) . . ?
C13 C14 C15 119.6(12) . . ?
C13 C14 C20 118.1(8) . . ?
C15 C14 C20 122.2(12) . . ?
C14 C15 C19 117.8(12) . . ?
C16 C15 C14 121.2(11) . . ?
C16 C15 C19 120.5(8) . . ?
C15 C16 H16 120.7 . . ?
C15 C16 C17 118.7(8) . . ?
C17 C16 H16 120.7 . . ?
N4 C17 C16 133.1(7) . . ?
N4 C17 C18 108.1(8) . . ?
C16 C17 C18 118.1(10) . . ?
N5 C18 C17 106.2(9) . . ?
C13 C18 N5 130.9(7) . . ?
C13 C18 C17 122.7(9) . . ?
C15 C19 H19A 109.5 . . ?
C15 C19 H19B 109.5 . . ?
C15 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C14 C20 H20A 109.5 . . ?
C14 C20 H20B 109.5 . . ?
C14 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C21 N6 H6 127.0 . . ?
C26 N6 H6 127.0 . . ?
C26 N6 C21 106.0(9) . . ?
C21 N7 H7A 126.7 . . ?
C21 N7 C27 106.7(7) . . ?
C27 N7 H7A 126.7 . . ?
N6 C21 H21 123.1 . . ?
N7 C21 N6 113.7(10) . . ?
N7 C21 H21 123.1 . . ?
C23 C22 H22 120.9 . . ?
C27 C22 H22 120.9 . . ?
C27 C22 C23 118.3(9) . . ?
C22 C23 C29 118.5(9) . . ?
C24 C23 C22 121.4(13) . . ?
C24 C23 C29 120.1(10) . . ?
C23 C24 C25 122.3(10) . . ?
C23 C24 C28 121.2(13) . . ?
C25 C24 C28 116.5(10) . . ?
C24 C25 H25 120.9 . . ?
C24 C25 C26 118.3(8) . . ?
C26 C25 H25 120.9 . . ?
N6 C26 C25 135.3(8) . . ?
N6 C26 C27 107.9(7) . . ?
C27 C26 C25 116.5(11) . . ?
N7 C27 C26 105.5(9) . . ?
C22 C27 N7 131.4(7) . . ?
C22 C27 C26 123.1(8) . . ?
C24 C28 H28A 109.5 . . ?
C24 C28 H28B 109.5 . . ?
C24 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C23 C29 H29A 109.5 . . ?
C23 C29 H29B 109.5 . . ?
C23 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 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 -0.7(16) . . . . ?
N1 C8 C9 C4 -175.9(12) . . . . ?
C2 N1 C8 C7 177.3(15) . . . . ?
C2 N1 C8 C9 -0.8(16) . . . . ?
C2 N3 C9 C4 176.0(17) . . . . ?
C2 N3 C9 C8 2.0(16) . . . . ?
C4 C5 C6 C7 1(3) . . . . ?
C4 C5 C6 C10 178.0(15) . . . . ?
C5 C4 C9 N3 -177.1(16) . . . . ?
C5 C4 C9 C8 -3(2) . . . . ?
C5 C6 C7 C8 1(3) . . . . ?
C6 C7 C8 N1 177.6(16) . . . . ?
C6 C7 C8 C9 -5(2) . . . . ?
C7 C8 C9 N3 -179.0(13) . . . . ?
C7 C8 C9 C4 6(2) . . . . ?
C8 N1 C2 N3 2.2(17) . . . . ?
C9 N3 C2 N1 -2.6(17) . . . . ?
C9 C4 C5 C6 0(2) . . . . ?
C9 C4 C5 C11 178.4(17) . . . . ?
C10 C6 C7 C8 -175.8(15) . . . . ?
C11 C5 C6 C7 -177.1(16) . . . . ?
C11 C5 C6 C10 0(2) . . . . ?
N4 C17 C18 N5 6.1(17) . . . . ?
N4 C17 C18 C13 -179.1(14) . . . . ?
C12 N4 C17 C16 -173.4(18) . . . . ?
C12 N4 C17 C18 -3.1(18) . . . . ?
C12 N5 C18 C13 179.2(17) . . . . ?
C12 N5 C18 C17 -6.6(17) . . . . ?
C13 C14 C15 C16 5(3) . . . . ?
C13 C14 C15 C19 177.6(16) . . . . ?
C14 C13 C18 N5 178.8(17) . . . . ?
C14 C13 C18 C17 5(2) . . . . ?
C14 C15 C16 C17 -7(3) . . . . ?
C15 C16 C17 N4 177.2(15) . . . . ?
C15 C16 C17 C18 8(2) . . . . ?
C16 C17 C18 N5 178.1(14) . . . . ?
C16 C17 C18 C13 -7(2) . . . . ?
C17 N4 C12 N5 -1(2) . . . . ?
C18 N5 C12 N4 5(2) . . . . ?
C18 C13 C14 C15 -4(3) . . . . ?
C18 C13 C14 C20 172.3(15) . . . . ?
C19 C15 C16 C17 -179.1(17) . . . . ?
C20 C14 C15 C16 -171.2(16) . . . . ?
C20 C14 C15 C19 1(3) . . . . ?
N6 C26 C27 N7 -3.2(16) . . . . ?
N6 C26 C27 C22 179.5(14) . . . . ?
C21 N6 C26 C25 175.2(19) . . . . ?
C21 N6 C26 C27 1.3(16) . . . . ?
C21 N7 C27 C22 -179.1(16) . . . . ?
C21 N7 C27 C26 3.9(16) . . . . ?
C22 C23 C24 C25 -1(3) . . . . ?
C22 C23 C24 C28 -179.0(17) . . . . ?
C23 C22 C27 N7 -178.3(15) . . . . ?
C23 C22 C27 C26 -2(2) . . . . ?
C23 C24 C25 C26 4(3) . . . . ?
C24 C25 C26 N6 -178.5(17) . . . . ?
C24 C25 C26 C27 -5(2) . . . . ?
C25 C26 C27 N7 -178.4(12) . . . . ?
C25 C26 C27 C22 4(2) . . . . ?
C26 N6 C21 N7 1.3(18) . . . . ?
C27 N7 C21 N6 -3.3(18) . . . . ?
C27 C22 C23 C24 0(3) . . . . ?
C27 C22 C23 C29 -179.2(16) . . . . ?
C28 C24 C25 C26 -178.2(16) . . . . ?
C29 C23 C24 C25 178.1(17) . . . . ?
C29 C23 C24 C28 0(3) . . . . ?

_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_0.28GPa
_database_code_depnum_ccdc_archive 'CCDC 1050859'
_audit_update_record             
;
2015-05-28 deposited with the CCDC.
2015-06-01 downloaded from the CCDC.
;
_audit_creation_date             2015-05-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-4
_chemical_name_common            '5,6-dimethylbenzimidazole phase beta'
_chemical_name_systematic        
;
 5,6-dimethylbenzimidazole phase beta
;
_chemical_formula_moiety         '0.33(C27 H30 N6)'
_chemical_formula_sum            'C9 H10 N2'
_chemical_formula_weight         146.19
_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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_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                   6.5011(10)
_cell_length_b                   27.23(2)
_cell_length_c                   13.949(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.615(15)
_cell_angle_gamma                90
_cell_volume                     2410(2)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    1339
_cell_measurement_temperature    296
_cell_measurement_theta_max      20.0580
_cell_measurement_theta_min      3.5740
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.14249
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_special_details           
;
 Data were collected at room temperature and pressure of 0.28(2) GPa
 (280000 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  0.2093
_diffrn_reflns_av_unetI/netI     0.2023
_diffrn_reflns_Laue_measured_fraction_full 0.460
_diffrn_reflns_Laue_measured_fraction_max 0.419
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14463
_diffrn_reflns_point_group_measured_fraction_full 0.460
_diffrn_reflns_point_group_measured_fraction_max 0.419
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.537
_diffrn_reflns_theta_min         3.742
_diffrn_ambient_temperature      296
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2413
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.460
_diffrn_measured_fraction_theta_max 0.419
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 phi    -35.00   19.75   0.7500   10.0000
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   12.0000
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   12.0000
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   12.0000
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   12.0000
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   12.0000
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   12.0000
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   12.0000
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   12.0000
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   12.0000
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   12.0000
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   12.0000
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   12.0000
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   12.0000
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   12.0000
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   12.0000
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      -0.0235227000
_diffrn_orient_matrix_UB_12      -0.0251774000
_diffrn_orient_matrix_UB_13      -0.0100002000
_diffrn_orient_matrix_UB_21      -0.0010144000
_diffrn_orient_matrix_UB_22      0.0040130000
_diffrn_orient_matrix_UB_23      -0.0503150000
_diffrn_orient_matrix_UB_31      0.1093262000
_diffrn_orient_matrix_UB_32      -0.0053681000
_diffrn_orient_matrix_UB_33      0.0090080000
_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                785
_reflns_number_total             2331
_reflns_odcompleteness_completeness 43.09
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.48
_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, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         2331
_refine_ls_number_restraints     459
_refine_ls_R_factor_all          0.2814
_refine_ls_R_factor_gt           0.1163
_refine_ls_restrained_S_all      0.972
_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          0.2809
_refine_ls_wR_factor_ref         0.3944
_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
2. Uiso/Uaniso restraints and constraints
Uanis(C5) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(N3) \\sim Ueq, Uanis(C16) \\sim
Ueq, Uanis(C8) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C4)
\\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C9) \\sim Ueq,
Uanis(C10) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C28)
\\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C29) \\sim Ueq,
Uanis(C13) \\sim Ueq, Uanis(C26) \\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(N6)
\\sim Ueq, Uanis(N7) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(N5) \\sim Ueq,
Uanis(C17) \\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C27)
\\sim Ueq, Uanis(C25) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C22) \\sim Ueq,
Uanis(N4) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Rigid body (RIGU) restrains
 N1, N3, C2, C4, C5, C6, C7, C8, C9, C10, H10A, C11, N4, N5, N6, N7, C12, C13,
 C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Fixed Sof: H1(0.5) H3(0.5) H4(0.5) H5(0.5) H6(0.5) H7(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), C2(H2), C4(H4A), C7(H7A), N4(H4), N5(H5), N6(H6), N7(H7),
 C12(H12), C13(H13), C16(H16), C21(H21), C22(H22), C25(H25)
5.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C)
;
_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
N1 N 0.0106(9) 0.1357(4) 0.7213(4) 0.076(3) Uani 1 1 d . U . . .
H1 H 0.0491 0.1381 0.7842 0.092 Uiso 0.5 1 calc R . P . .
N3 N 0.0020(9) 0.1117(4) 0.5676(4) 0.083(3) Uani 1 1 d . U . . .
H3 H 0.0387 0.0962 0.5202 0.099 Uiso 0.5 1 calc R . P . .
C2 C 0.1032(12) 0.1127(6) 0.6631(6) 0.087(3) Uani 1 1 d . U . . .
H2 H 0.2331 0.0976 0.6852 0.104 Uiso 1 1 calc R . . . .
C4 C -0.3396(11) 0.1539(6) 0.4866(5) 0.080(3) Uani 1 1 d . U . . .
H4A H -0.3422 0.1439 0.4226 0.096 Uiso 1 1 calc R . . . .
C5 C -0.5012(12) 0.1821(7) 0.5084(6) 0.094(3) Uani 1 1 d . U . . .
C6 C -0.4908(11) 0.1982(6) 0.6052(6) 0.083(3) Uani 1 1 d . U . . .
C7 C -0.3287(12) 0.1843(6) 0.6791(6) 0.081(3) Uani 1 1 d . U . . .
H7A H -0.3275 0.1939 0.7432 0.098 Uiso 1 1 calc R . . . .
C8 C -0.1660(11) 0.1561(5) 0.6604(5) 0.068(3) Uani 1 1 d . U . . .
C9 C -0.1750(11) 0.1412(5) 0.5630(5) 0.072(3) Uani 1 1 d . U . . .
C10 C -0.6664(12) 0.2332(7) 0.6279(8) 0.121(5) Uani 1 1 d . U . . .
H10A H -0.6696 0.2629 0.5905 0.181 Uiso 1 1 calc GR U . . .
H10B H -0.6359 0.2409 0.6967 0.181 Uiso 1 1 calc GR . . . .
H10C H -0.8008 0.2171 0.6102 0.181 Uiso 1 1 calc GR . . . .
C11 C -0.6789(13) 0.2012(6) 0.4251(7) 0.118(5) Uani 1 1 d . U . . .
H11A H -0.6483 0.1929 0.3628 0.177 Uiso 1 1 calc GR . . . .
H11B H -0.6892 0.2362 0.4302 0.177 Uiso 1 1 calc GR . . . .
H11C H -0.8101 0.1864 0.4304 0.177 Uiso 1 1 calc GR . . . .
N4 N 0.0721(10) 0.0640(5) 0.3999(4) 0.090(3) Uani 1 1 d . U . . .
H4 H 0.1029 0.0706 0.4616 0.108 Uiso 0.5 1 calc R . P . .
N5 N 0.0864(9) 0.0601(5) 0.2428(4) 0.082(3) Uani 1 1 d . U . . .
H5 H 0.1323 0.0645 0.1901 0.098 Uiso 0.5 1 calc R . P . .
N6 N 0.2160(9) 0.0901(5) 0.0732(4) 0.083(3) Uani 1 1 d . U . . .
H6 H 0.1957 0.0736 0.1229 0.100 Uiso 0.5 1 calc R . P . .
N7 N 0.1728(9) 0.1203(4) -0.0784(4) 0.078(3) Uani 1 1 d . U . . .
H7 H 0.1171 0.1257 -0.1393 0.093 Uiso 0.5 1 calc R . P . .
C12 C 0.1770(12) 0.0762(6) 0.3340(6) 0.088(4) Uani 1 1 d . U . . .
H12 H 0.3016 0.0942 0.3481 0.105 Uiso 1 1 calc R . . . .
C13 C -0.2496(12) 0.0117(6) 0.1830(5) 0.080(3) Uani 1 1 d . U . . .
H13 H -0.2436 0.0102 0.1171 0.096 Uiso 1 1 calc R . . . .
C14 C -0.4127(11) -0.0094(6) 0.2155(6) 0.086(3) Uani 1 1 d . U . . .
C15 C -0.4165(11) -0.0088(7) 0.3151(6) 0.085(3) Uani 1 1 d . U . . .
C16 C -0.2623(11) 0.0147(6) 0.3821(6) 0.083(3) Uani 1 1 d . U . . .
H16 H -0.2655 0.0153 0.4484 0.099 Uiso 1 1 calc R . . . .
C17 C -0.1013(11) 0.0376(6) 0.3482(5) 0.079(3) Uani 1 1 d . U . . .
C18 C -0.0938(11) 0.0352(6) 0.2507(5) 0.075(3) Uani 1 1 d . U . . .
C19 C -0.5859(13) -0.0375(8) 0.3542(7) 0.126(5) Uani 1 1 d . U . . .
H19A H -0.7223 -0.0238 0.3272 0.189 Uiso 1 1 calc GR . . . .
H19B H -0.5571 -0.0352 0.4246 0.189 Uiso 1 1 calc GR . . . .
H19C H -0.5836 -0.0714 0.3352 0.189 Uiso 1 1 calc GR . . . .
C20 C -0.5850(12) -0.0379(7) 0.1427(8) 0.114(5) Uani 1 1 d . U . . .
H20A H -0.5900 -0.0265 0.0771 0.171 Uiso 1 1 calc GR . . . .
H20B H -0.7192 -0.0325 0.1590 0.171 Uiso 1 1 calc GR . . . .
H20C H -0.5529 -0.0723 0.1467 0.171 Uiso 1 1 calc GR . . . .
C21 C 0.0924(11) 0.0919(6) -0.0151(5) 0.079(3) Uani 1 1 d . U . . .
H21 H -0.0359 0.0755 -0.0323 0.095 Uiso 1 1 calc R . . . .
C22 C 0.5112(11) 0.1694(6) -0.0518(5) 0.077(3) Uani 1 1 d . U . . .
H22 H 0.4929 0.1820 -0.1151 0.092 Uiso 1 1 calc R . . . .
C23 C 0.6839(11) 0.1802(6) 0.0185(5) 0.079(3) Uani 1 1 d . U . . .
C24 C 0.7090(11) 0.1669(6) 0.1155(6) 0.081(3) Uani 1 1 d . U . . .
C25 C 0.5605(11) 0.1332(6) 0.1411(5) 0.078(3) Uani 1 1 d . U . . .
H25 H 0.5812 0.1203 0.2042 0.094 Uiso 1 1 calc R . . . .
C26 C 0.3847(11) 0.1202(6) 0.0695(5) 0.072(3) Uani 1 1 d . U . . .
C27 C 0.3623(11) 0.1387(5) -0.0253(5) 0.066(3) Uani 1 1 d . U . . .
C28 C 0.8919(12) 0.1824(7) 0.1960(7) 0.119(5) Uani 1 1 d . U . . .
H28A H 1.0207 0.1702 0.1821 0.178 Uiso 1 1 calc GR . . . .
H28B H 0.8741 0.1693 0.2576 0.178 Uiso 1 1 calc GR . . . .
H28C H 0.8973 0.2176 0.1997 0.178 Uiso 1 1 calc GR . . . .
C29 C 0.8466(12) 0.2161(7) -0.0088(7) 0.113(5) Uani 1 1 d . U . . .
H29A H 0.8130 0.2218 -0.0784 0.170 Uiso 1 1 calc GR . . . .
H29B H 0.9851 0.2021 0.0101 0.170 Uiso 1 1 calc GR . . . .
H29C H 0.8426 0.2467 0.0250 0.170 Uiso 1 1 calc GR . . . .


_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
N1 H1 0.8600 . ?
N1 C2 1.275(12) . ?
N1 C8 1.386(10) . ?
N3 H3 0.8600 . ?
N3 C2 1.352(9) . ?
N3 C9 1.394(12) . ?
C2 H2 0.9300 . ?
C4 H4A 0.9300 . ?
C4 C5 1.387(15) . ?
C4 C9 1.379(10) . ?
C5 C6 1.408(13) . ?
C5 C11 1.540(12) . ?
C6 C7 1.358(11) . ?
C6 C10 1.571(17) . ?
C7 H7A 0.9300 . ?
C7 C8 1.377(13) . ?
C8 C9 1.407(10) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
N4 H4 0.8600 . ?
N4 C12 1.302(10) . ?
N4 C17 1.396(12) . ?
N5 H5 0.8600 . ?
N5 C12 1.353(11) . ?
N5 C18 1.379(11) . ?
N6 H6 0.8600 . ?
N6 C21 1.316(8) . ?
N6 C26 1.378(12) . ?
N7 H7 0.8600 . ?
N7 C21 1.361(13) . ?
N7 C27 1.385(10) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.367(12) . ?
C13 C18 1.382(13) . ?
C14 C15 1.396(11) . ?
C14 C20 1.545(15) . ?
C15 C16 1.372(13) . ?
C15 C19 1.543(15) . ?
C16 H16 0.9300 . ?
C16 C17 1.387(12) . ?
C17 C18 1.373(9) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C22 C23 1.352(9) . ?
C22 C27 1.389(14) . ?
C23 C24 1.376(11) . ?
C23 C29 1.547(16) . ?
C24 C25 1.432(15) . ?
C24 C28 1.507(11) . ?
C25 H25 0.9300 . ?
C25 C26 1.389(10) . ?
C26 C27 1.394(11) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 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
C2 N1 H1 127.8 . . ?
C2 N1 C8 104.4(6) . . ?
C8 N1 H1 127.8 . . ?
C2 N3 H3 127.7 . . ?
C2 N3 C9 104.6(8) . . ?
C9 N3 H3 127.7 . . ?
N1 C2 N3 116.3(8) . . ?
N1 C2 H2 121.9 . . ?
N3 C2 H2 121.9 . . ?
C5 C4 H4A 121.1 . . ?
C9 C4 H4A 121.1 . . ?
C9 C4 C5 117.8(8) . . ?
C4 C5 C6 120.2(8) . . ?
C4 C5 C11 120.1(8) . . ?
C6 C5 C11 119.3(11) . . ?
C5 C6 C10 119.8(8) . . ?
C7 C6 C5 120.5(10) . . ?
C7 C6 C10 119.6(9) . . ?
C6 C7 H7A 119.6 . . ?
C6 C7 C8 120.8(8) . . ?
C8 C7 H7A 119.6 . . ?
N1 C8 C9 109.3(8) . . ?
C7 C8 N1 132.4(7) . . ?
C7 C8 C9 118.2(8) . . ?
N3 C9 C8 105.2(7) . . ?
C4 C9 N3 132.3(8) . . ?
C4 C9 C8 122.4(9) . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C12 N4 H4 127.6 . . ?
C12 N4 C17 104.8(7) . . ?
C17 N4 H4 127.6 . . ?
C12 N5 H5 126.7 . . ?
C12 N5 C18 106.7(6) . . ?
C18 N5 H5 126.7 . . ?
C21 N6 H6 127.1 . . ?
C21 N6 C26 105.8(8) . . ?
C26 N6 H6 127.1 . . ?
C21 N7 H7 126.8 . . ?
C21 N7 C27 106.4(6) . . ?
C27 N7 H7 126.8 . . ?
N4 C12 N5 113.1(9) . . ?
N4 C12 H12 123.4 . . ?
N5 C12 H12 123.4 . . ?
C14 C13 H13 120.8 . . ?
C14 C13 C18 118.3(7) . . ?
C18 C13 H13 120.8 . . ?
C13 C14 C15 120.6(9) . . ?
C13 C14 C20 119.8(8) . . ?
C15 C14 C20 119.5(10) . . ?
C14 C15 C19 121.0(10) . . ?
C16 C15 C14 121.0(9) . . ?
C16 C15 C19 117.9(7) . . ?
C15 C16 H16 120.9 . . ?
C15 C16 C17 118.1(7) . . ?
C17 C16 H16 120.9 . . ?
C16 C17 N4 129.7(7) . . ?
C18 C17 N4 109.7(8) . . ?
C18 C17 C16 120.6(9) . . ?
N5 C18 C13 133.0(6) . . ?
C17 C18 N5 105.7(8) . . ?
C17 C18 C13 121.4(8) . . ?
C15 C19 H19A 109.5 . . ?
C15 C19 H19B 109.5 . . ?
C15 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C14 C20 H20A 109.5 . . ?
C14 C20 H20B 109.5 . . ?
C14 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N6 C21 N7 112.7(8) . . ?
N6 C21 H21 123.7 . . ?
N7 C21 H21 123.7 . . ?
C23 C22 H22 121.5 . . ?
C23 C22 C27 117.0(8) . . ?
C27 C22 H22 121.5 . . ?
C22 C23 C24 123.9(9) . . ?
C22 C23 C29 117.6(8) . . ?
C24 C23 C29 117.9(8) . . ?
C23 C24 C25 118.2(8) . . ?
C23 C24 C28 124.3(10) . . ?
C25 C24 C28 117.3(8) . . ?
C24 C25 H25 120.7 . . ?
C26 C25 C24 118.6(8) . . ?
C26 C25 H25 120.7 . . ?
N6 C26 C25 131.4(8) . . ?
N6 C26 C27 109.3(7) . . ?
C25 C26 C27 119.3(9) . . ?
N7 C27 C22 131.7(7) . . ?
N7 C27 C26 105.8(8) . . ?
C22 C27 C26 122.4(7) . . ?
C24 C28 H28A 109.5 . . ?
C24 C28 H28B 109.5 . . ?
C24 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C23 C29 H29A 109.5 . . ?
C23 C29 H29B 109.5 . . ?
C23 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 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 -0.4(13) . . . . ?
N1 C8 C9 C4 176.8(11) . . . . ?
C2 N1 C8 C7 179.0(14) . . . . ?
C2 N1 C8 C9 3.0(13) . . . . ?
C2 N3 C9 C4 -179.0(12) . . . . ?
C2 N3 C9 C8 -2.2(13) . . . . ?
C4 C5 C6 C7 -3(2) . . . . ?
C4 C5 C6 C10 175.7(13) . . . . ?
C5 C4 C9 N3 175.9(13) . . . . ?
C5 C4 C9 C8 -0.5(19) . . . . ?
C5 C6 C7 C8 3.1(19) . . . . ?
C6 C7 C8 N1 -177.2(12) . . . . ?
C6 C7 C8 C9 -1.5(19) . . . . ?
C7 C8 C9 N3 -177.1(11) . . . . ?
C7 C8 C9 C4 0.1(18) . . . . ?
C8 N1 C2 N3 -4.7(14) . . . . ?
C9 N3 C2 N1 4.5(15) . . . . ?
C9 C4 C5 C6 2(2) . . . . ?
C9 C4 C5 C11 174.6(11) . . . . ?
C10 C6 C7 C8 -176.0(13) . . . . ?
C11 C5 C6 C7 -176.0(12) . . . . ?
C11 C5 C6 C10 3.1(19) . . . . ?
N4 C17 C18 N5 0.2(14) . . . . ?
N4 C17 C18 C13 -179.0(12) . . . . ?
N6 C26 C27 N7 1.6(13) . . . . ?
N6 C26 C27 C22 -178.6(11) . . . . ?
C12 N4 C17 C16 178.1(14) . . . . ?
C12 N4 C17 C18 -0.2(14) . . . . ?
C12 N5 C18 C13 178.9(14) . . . . ?
C12 N5 C18 C17 -0.2(14) . . . . ?
C13 C14 C15 C16 3(2) . . . . ?
C13 C14 C15 C19 -173.0(13) . . . . ?
C14 C13 C18 N5 -179.1(14) . . . . ?
C14 C13 C18 C17 -0.2(19) . . . . ?
C14 C15 C16 C17 0(2) . . . . ?
C15 C16 C17 N4 179.7(13) . . . . ?
C15 C16 C17 C18 -2.2(19) . . . . ?
C16 C17 C18 N5 -178.2(12) . . . . ?
C16 C17 C18 C13 3(2) . . . . ?
C17 N4 C12 N5 0.1(15) . . . . ?
C18 N5 C12 N4 0.1(16) . . . . ?
C18 C13 C14 C15 -3(2) . . . . ?
C18 C13 C14 C20 -177.5(12) . . . . ?
C19 C15 C16 C17 175.5(12) . . . . ?
C20 C14 C15 C16 177.9(12) . . . . ?
C20 C14 C15 C19 2(2) . . . . ?
C21 N6 C26 C25 178.4(13) . . . . ?
C21 N6 C26 C27 -2.2(13) . . . . ?
C21 N7 C27 C22 179.8(13) . . . . ?
C21 N7 C27 C26 -0.4(13) . . . . ?
C22 C23 C24 C25 10(2) . . . . ?
C22 C23 C24 C28 -174.5(13) . . . . ?
C23 C22 C27 N7 -179.2(11) . . . . ?
C23 C22 C27 C26 1.1(18) . . . . ?
C23 C24 C25 C26 -7.6(18) . . . . ?
C24 C25 C26 N6 -178.2(13) . . . . ?
C24 C25 C26 C27 2.3(17) . . . . ?
C25 C26 C27 N7 -178.8(10) . . . . ?
C25 C26 C27 C22 0.9(18) . . . . ?
C26 N6 C21 N7 1.9(13) . . . . ?
C27 N7 C21 N6 -1.0(14) . . . . ?
C27 C22 C23 C24 -7(2) . . . . ?
C27 C22 C23 C29 -177.5(12) . . . . ?
C28 C24 C25 C26 176.8(11) . . . . ?
C29 C23 C24 C25 -179.2(12) . . . . ?
C29 C23 C24 C28 -3.9(19) . . . . ?

_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_0.33GPa
_database_code_depnum_ccdc_archive 'CCDC 1050860'
_audit_update_record             
;
2015-05-28 deposited with the CCDC.
2015-06-01 downloaded from the CCDC.
;
_audit_creation_date             2015-05-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-4
_chemical_name_common            '5,6-dimethylbenzimidazole phase beta'
_chemical_name_systematic        
;
 5,6-dimethylbenzimidazole phase beta
;
_chemical_formula_moiety         '0.33(C9 H10 N2), 0.33(C18 H19 N4)'
_chemical_formula_sum            'C9 H9.67 N2'
_chemical_formula_weight         145.85
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C9 H10 N2'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_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                   6.538(3)
_cell_length_b                   26.99(14)
_cell_length_c                   13.930(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.68(4)
_cell_angle_gamma                90
_cell_volume                     2398(13)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    727
_cell_measurement_temperature    296
_cell_measurement_theta_max      22.4090
_cell_measurement_theta_min      3.2250
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36335
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             932
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_special_details           
;
 Data were collected at room temperature and pressure of 0.33(2) GPa
 (330000 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  0.2049
_diffrn_reflns_av_unetI/netI     0.1310
_diffrn_reflns_Laue_measured_fraction_full 0.264
_diffrn_reflns_Laue_measured_fraction_max 0.233
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14260
_diffrn_reflns_point_group_measured_fraction_full 0.264
_diffrn_reflns_point_group_measured_fraction_max 0.233
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.079
_diffrn_reflns_theta_min         2.998
_diffrn_ambient_temperature      296
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0772
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.264
_diffrn_measured_fraction_theta_max 0.233
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 phi    -35.00   19.60   0.7000   30.0000
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   30.0000
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   30.0000
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   30.0000
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   30.0000
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   30.0000
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   30.0000
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   30.0000
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   30.0000
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   30.0000
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   30.0000
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   30.0000
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   30.0000
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   30.0000
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   30.0000
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   30.0000
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      -0.0028054000
_diffrn_orient_matrix_UB_12      -0.0262098000
_diffrn_orient_matrix_UB_13      0.0000032000
_diffrn_orient_matrix_UB_21      0.0014843000
_diffrn_orient_matrix_UB_22      0.0001557000
_diffrn_orient_matrix_UB_23      0.0510473000
_diffrn_orient_matrix_UB_31      -0.1114639000
_diffrn_orient_matrix_UB_32      0.0006447000
_diffrn_orient_matrix_UB_33      -0.0106838000
_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                546
_reflns_number_total             1358
_reflns_odcompleteness_completeness 24.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.02
_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, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.114
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         1358
_refine_ls_number_restraints     285
_refine_ls_R_factor_all          0.2291
_refine_ls_R_factor_gt           0.0883
_refine_ls_restrained_S_all      0.971
_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)+(0.1370P)²+1.9930P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2049
_refine_ls_wR_factor_ref         0.2909
_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
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 0.08A with sigma of 0.04 and
sigma for terminal atoms of 0.08
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.01 and sigma
for terminal atoms of 0.01
4. Others
 Fixed Sof: H1(0.5) H3(0.5) H4(0.5) H5(0.5) H6(0.5) H7(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), C2(H2), C4(H4A), C7(H7A), N4(H4), N5(H5), N6(H6), N7(H7),
 C12(H12), C13(H13), C16(H16), C21(H21), C22(H22), C25(H25)
5.b X=CH2 refined with riding coordinates:
 C29(H29A,H29B)
5.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C28(H28A,H28B,H28C)
;
_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
N1 N 0.0083(12) 0.1371(9) 0.7209(5) 0.066(5) Uani 1 1 d . U . . .
H1 H 0.0475 0.1406 0.7837 0.079 Uiso 0.5 1 calc R . P . .
N3 N 0.0014(12) 0.1128(9) 0.5687(5) 0.069(4) Uani 1 1 d . U . . .
H3 H 0.0390 0.0983 0.5203 0.083 Uiso 0.5 1 calc R . P . .
C2 C 0.1038(15) 0.1118(12) 0.6632(7) 0.076(5) Uani 1 1 d . U . . .
H2 H 0.2293 0.0949 0.6856 0.091 Uiso 1 1 calc R . . . .
C4 C -0.3382(14) 0.1550(11) 0.4874(6) 0.068(5) Uani 1 1 d . U . . .
H4A H -0.3372 0.1465 0.4227 0.082 Uiso 1 1 calc R . . . .
C5 C -0.4997(16) 0.1809(12) 0.5086(7) 0.078(5) Uani 1 1 d . U . . .
C6 C -0.4934(15) 0.1984(12) 0.6072(7) 0.077(5) Uani 1 1 d . U . . .
C7 C -0.3256(14) 0.1840(11) 0.6798(6) 0.066(5) Uani 1 1 d . U . . .
H7A H -0.3221 0.1934 0.7444 0.080 Uiso 1 1 calc R . . . .
C8 C -0.1661(14) 0.1568(10) 0.6609(6) 0.052(4) Uani 1 1 d . U . . .
C9 C -0.1749(14) 0.1413(11) 0.5635(6) 0.059(5) Uani 1 1 d . U . . .
C10 C -0.6625(16) 0.2349(12) 0.6286(9) 0.106(6) Uani 1 1 d . U . . .
H10A H -0.6895 0.2601 0.5786 0.159 Uiso 1 1 calc GR . . . .
H10B H -0.6126 0.2502 0.6917 0.159 Uiso 1 1 calc GR . . . .
H10C H -0.7895 0.2171 0.6287 0.159 Uiso 1 1 calc GR . . . .
C11 C -0.6773(17) 0.1998(13) 0.4251(8) 0.103(6) Uani 1 1 d . U . . .
H11A H -0.6445 0.1923 0.3628 0.155 Uiso 1 1 calc GR . . . .
H11B H -0.6920 0.2349 0.4312 0.155 Uiso 1 1 calc GR . . . .
H11C H -0.8062 0.1838 0.4292 0.155 Uiso 1 1 calc GR . . . .
N4 N 0.0712(12) 0.0640(9) 0.3996(5) 0.068(4) Uani 1 1 d . U . . .
H4 H 0.1023 0.0703 0.4616 0.082 Uiso 0.5 1 calc R . P . .
N5 N 0.0848(12) 0.0606(9) 0.2421(5) 0.072(5) Uani 1 1 d . U . . .
H5 H 0.1335 0.0636 0.1898 0.087 Uiso 0.5 1 calc R . P . .
N6 N 0.2130(12) 0.0901(9) 0.0724(5) 0.071(4) Uani 1 1 d . U . . .
H6 H 0.1888 0.0736 0.1216 0.085 Uiso 0.5 1 calc R . P . .
N7 N 0.1722(11) 0.1194(8) -0.0783(5) 0.056(4) Uani 1 1 d . U . . .
H7 H 0.1172 0.1235 -0.1398 0.067 Uiso 0.5 1 calc R . P . .
C12 C 0.1750(16) 0.0779(12) 0.3343(7) 0.079(5) Uani 1 1 d . U . . .
H12 H 0.2958 0.0971 0.3485 0.095 Uiso 1 1 calc R . . . .
C13 C -0.2482(15) 0.0122(11) 0.1822(6) 0.071(5) Uani 1 1 d . U . . .
H13 H -0.2412 0.0109 0.1163 0.085 Uiso 1 1 calc R . . . .
C14 C -0.4124(16) -0.0118(12) 0.2141(7) 0.078(5) Uani 1 1 d . U . . .
C15 C -0.4161(15) -0.0070(12) 0.3173(8) 0.079(5) Uani 1 1 d . U . . .
C16 C -0.2608(15) 0.0153(11) 0.3807(7) 0.072(5) Uani 1 1 d . U . . .
H16 H -0.2632 0.0161 0.4472 0.086 Uiso 1 1 calc R . . . .
C17 C -0.0991(14) 0.0369(11) 0.3495(6) 0.059(5) Uani 1 1 d . U . . .
C18 C -0.0959(15) 0.0380(10) 0.2496(5) 0.058(5) Uani 1 1 d . U . . .
C19 C -0.5848(17) -0.0367(13) 0.3534(9) 0.116(6) Uani 1 1 d . U . . .
H19A H -0.7208 -0.0237 0.3239 0.174 Uiso 1 1 calc GR . . . .
H19B H -0.5618 -0.0341 0.4237 0.174 Uiso 1 1 calc GR . . . .
H19C H -0.5773 -0.0709 0.3352 0.174 Uiso 1 1 calc GR . . . .
C20 C -0.5867(17) -0.0363(13) 0.1411(8) 0.105(5) Uani 1 1 d . U . . .
H20A H -0.7185 -0.0222 0.1466 0.158 Uiso 1 1 calc GR . . . .
H20B H -0.5869 -0.0712 0.1545 0.158 Uiso 1 1 calc GR . . . .
H20C H -0.5659 -0.0311 0.0758 0.158 Uiso 1 1 calc GR . . . .
C21 C 0.0918(14) 0.0930(10) -0.0168(6) 0.065(5) Uani 1 1 d . U . . .
H21 H -0.0386 0.0777 -0.0343 0.078 Uiso 1 1 calc R . . . .
C22 C 0.5111(14) 0.1689(11) -0.0517(6) 0.065(5) Uani 1 1 d . U . . .
H22 H 0.4984 0.1782 -0.1170 0.079 Uiso 1 1 calc R . . . .
C23 C 0.6828(15) 0.1853(12) 0.0188(7) 0.071(5) Uani 1 1 d . U . . .
C24 C 0.7058(15) 0.1621(13) 0.1173(7) 0.074(5) Uani 1 1 d . U . . .
C25 C 0.5593(15) 0.1328(11) 0.1413(6) 0.065(5) Uani 1 1 d . U . . .
H25 H 0.5749 0.1220 0.2058 0.078 Uiso 1 1 calc R . . . .
C26 C 0.3839(15) 0.1185(11) 0.0705(6) 0.063(5) Uani 1 1 d . U . . .
C27 C 0.3632(14) 0.1398(10) -0.0274(5) 0.053(4) Uani 1 1 d . U . . .
C28 C 0.8941(14) 0.1834(12) 0.1964(8) 0.093(5) Uani 1 1 d . U . . .
H28A H 1.0236 0.1749 0.1787 0.140 Uiso 1 1 calc GR . . . .
H28B H 0.8919 0.1695 0.2596 0.140 Uiso 1 1 calc GR . . . .
H28C H 0.8819 0.2188 0.1992 0.140 Uiso 1 1 calc GR . . . .
C29 C 0.8462(16) 0.2151(12) -0.0053(9) 0.101(5) Uani 1 1 d . U . . .
H29A H 0.8401 0.2241 -0.0703 0.121 Uiso 1 1 calc R . . . .
H29B H 0.9583 0.2253 0.0441 0.121 Uiso 1 1 calc R . . . .


_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
N1 H1 0.8600 . ?
N1 C2 1.31(2) . ?
N1 C8 1.365(16) . ?
N3 H3 0.8600 . ?
N3 C2 1.341(10) . ?
N3 C9 1.37(2) . ?
C2 H2 0.9300 . ?
C4 H4A 0.9300 . ?
C4 C5 1.35(2) . ?
C4 C9 1.379(15) . ?
C5 C6 1.445(19) . ?
C5 C11 1.54(2) . ?
C6 C7 1.374(16) . ?
C6 C10 1.56(3) . ?
C7 H7A 0.9300 . ?
C7 C8 1.35(2) . ?
C8 C9 1.410(15) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
N4 H4 0.8600 . ?
N4 C12 1.304(15) . ?
N4 C17 1.38(2) . ?
N5 H5 0.8600 . ?
N5 C12 1.371(16) . ?
N5 C18 1.354(18) . ?
N6 H6 0.8600 . ?
N6 C21 1.321(10) . ?
N6 C26 1.36(2) . ?
N7 H7 0.8600 . ?
N7 C21 1.311(19) . ?
N7 C27 1.405(15) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.41(2) . ?
C13 C18 1.40(2) . ?
C14 C15 1.448(14) . ?
C14 C20 1.50(2) . ?
C15 C16 1.33(2) . ?
C15 C19 1.54(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.36(2) . ?
C17 C18 1.396(10) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C22 C23 1.392(17) . ?
C22 C27 1.35(2) . ?
C23 C24 1.48(2) . ?
C23 C29 1.43(3) . ?
C24 C25 1.34(3) . ?
C24 C28 1.57(2) . ?
C25 H25 0.9300 . ?
C25 C26 1.393(15) . ?
C26 C27 1.459(19) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9300 . ?
C29 H29B 0.9300 . ?

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
C2 N1 H1 127.1 . . ?
C2 N1 C8 105.9(9) . . ?
C8 N1 H1 127.1 . . ?
C2 N3 H3 126.4 . . ?
C2 N3 C9 107.2(12) . . ?
C9 N3 H3 126.4 . . ?
N1 C2 N3 112.9(13) . . ?
N1 C2 H2 123.5 . . ?
N3 C2 H2 123.5 . . ?
C5 C4 H4A 120.6 . . ?
C5 C4 C9 118.7(11) . . ?
C9 C4 H4A 120.6 . . ?
C4 C5 C6 121.0(11) . . ?
C4 C5 C11 120.1(12) . . ?
C6 C5 C11 118.1(18) . . ?
C5 C6 C10 121.0(13) . . ?
C7 C6 C5 117.3(16) . . ?
C7 C6 C10 121.5(13) . . ?
C6 C7 H7A 118.8 . . ?
C8 C7 C6 122.5(11) . . ?
C8 C7 H7A 118.8 . . ?
N1 C8 C9 109.0(14) . . ?
C7 C8 N1 132.1(9) . . ?
C7 C8 C9 118.7(11) . . ?
N3 C9 C4 133.5(12) . . ?
N3 C9 C8 105.0(10) . . ?
C4 C9 C8 121.4(16) . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C12 N4 H4 126.8 . . ?
C12 N4 C17 106.5(10) . . ?
C17 N4 H4 126.8 . . ?
C12 N5 H5 126.8 . . ?
C18 N5 H5 126.8 . . ?
C18 N5 C12 106.4(9) . . ?
C21 N6 H6 127.0 . . ?
C21 N6 C26 105.9(12) . . ?
C26 N6 H6 127.0 . . ?
C21 N7 H7 125.6 . . ?
C21 N7 C27 108.8(8) . . ?
C27 N7 H7 125.6 . . ?
N4 C12 N5 111.9(15) . . ?
N4 C12 H12 124.0 . . ?
N5 C12 H12 124.0 . . ?
C14 C13 H13 120.0 . . ?
C18 C13 H13 120.0 . . ?
C18 C13 C14 119.9(9) . . ?
C13 C14 C15 116.8(15) . . ?
C13 C14 C20 120.4(10) . . ?
C15 C14 C20 122.4(13) . . ?
C14 C15 C19 116.6(16) . . ?
C16 C15 C14 121.5(13) . . ?
C16 C15 C19 121.1(11) . . ?
C15 C16 H16 119.6 . . ?
C15 C16 C17 120.9(10) . . ?
C17 C16 H16 119.6 . . ?
N4 C17 C18 107.8(13) . . ?
C16 C17 N4 131.3(9) . . ?
C16 C17 C18 120.7(13) . . ?
N5 C18 C13 132.7(8) . . ?
N5 C18 C17 106.9(11) . . ?
C17 C18 C13 119.7(15) . . ?
C15 C19 H19A 109.5 . . ?
C15 C19 H19B 109.5 . . ?
C15 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C14 C20 H20A 109.5 . . ?
C14 C20 H20B 109.5 . . ?
C14 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N6 C21 H21 123.1 . . ?
N7 C21 N6 113.8(12) . . ?
N7 C21 H21 123.1 . . ?
C23 C22 H22 119.3 . . ?
C27 C22 H22 119.3 . . ?
C27 C22 C23 121.4(11) . . ?
C22 C23 C24 114.9(18) . . ?
C22 C23 C29 122.7(12) . . ?
C29 C23 C24 121.5(11) . . ?
C23 C24 C28 113.5(19) . . ?
C25 C24 C23 123.1(11) . . ?
C25 C24 C28 122.3(12) . . ?
C24 C25 H25 119.6 . . ?
C24 C25 C26 120.7(12) . . ?
C26 C25 H25 119.6 . . ?
N6 C26 C25 134.1(12) . . ?
N6 C26 C27 109.4(10) . . ?
C25 C26 C27 116.4(16) . . ?
N7 C27 C26 102.0(14) . . ?
C22 C27 N7 135.2(9) . . ?
C22 C27 C26 122.7(10) . . ?
C24 C28 H28A 109.5 . . ?
C24 C28 H28B 109.5 . . ?
C24 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C23 C29 H29A 120.0 . . ?
C23 C29 H29B 120.0 . . ?
H29A C29 H29B 120.0 . . ?

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(2) . . . . ?
N1 C8 C9 C4 179(2) . . . . ?
C2 N1 C8 C7 177(2) . . . . ?
C2 N1 C8 C9 1(2) . . . . ?
C2 N3 C9 C4 -179(3) . . . . ?
C2 N3 C9 C8 0(2) . . . . ?
C4 C5 C6 C7 -5(4) . . . . ?
C4 C5 C6 C10 171(2) . . . . ?
C5 C4 C9 N3 175(3) . . . . ?
C5 C4 C9 C8 -5(3) . . . . ?
C5 C6 C7 C8 3(3) . . . . ?
C6 C7 C8 N1 -177(2) . . . . ?
C6 C7 C8 C9 -2(3) . . . . ?
C7 C8 C9 N3 -177(2) . . . . ?
C7 C8 C9 C4 3(3) . . . . ?
C8 N1 C2 N3 -1(3) . . . . ?
C9 N3 C2 N1 0(3) . . . . ?
C9 C4 C5 C6 6(4) . . . . ?
C9 C4 C5 C11 176(2) . . . . ?
C10 C6 C7 C8 -173(2) . . . . ?
C11 C5 C6 C7 -176(2) . . . . ?
C11 C5 C6 C10 0(3) . . . . ?
N4 C17 C18 N5 6(3) . . . . ?
N4 C17 C18 C13 178(2) . . . . ?
N6 C26 C27 N7 -2(2) . . . . ?
N6 C26 C27 C22 -178.7(18) . . . . ?
C12 N4 C17 C16 -178(3) . . . . ?
C12 N4 C17 C18 -3(3) . . . . ?
C12 N5 C18 C13 -177(3) . . . . ?
C12 N5 C18 C17 -7(3) . . . . ?
C13 C14 C15 C16 -6(4) . . . . ?
C13 C14 C15 C19 -175(2) . . . . ?
C14 C13 C18 N5 174(2) . . . . ?
C14 C13 C18 C17 4(3) . . . . ?
C14 C15 C16 C17 4(4) . . . . ?
C15 C16 C17 N4 176(3) . . . . ?
C15 C16 C17 C18 3(4) . . . . ?
C16 C17 C18 N5 -179(2) . . . . ?
C16 C17 C18 C13 -7(4) . . . . ?
C17 N4 C12 N5 -1(3) . . . . ?
C18 N5 C12 N4 5(3) . . . . ?
C18 C13 C14 C15 2(3) . . . . ?
C18 C13 C14 C20 175(2) . . . . ?
C19 C15 C16 C17 173(2) . . . . ?
C20 C14 C15 C16 -179(2) . . . . ?
C20 C14 C15 C19 12(3) . . . . ?
C21 N6 C26 C25 175(2) . . . . ?
C21 N6 C26 C27 0(2) . . . . ?
C21 N7 C27 C22 180(2) . . . . ?
C21 N7 C27 C26 3(2) . . . . ?
C22 C23 C24 C25 -9(3) . . . . ?
C22 C23 C24 C28 -177.1(19) . . . . ?
C23 C22 C27 N7 176(2) . . . . ?
C23 C22 C27 C26 -8(3) . . . . ?
C23 C24 C25 C26 7(4) . . . . ?
C24 C25 C26 N6 -180(3) . . . . ?
C24 C25 C26 C27 -4(3) . . . . ?
C25 C26 C27 N7 -178.3(17) . . . . ?
C25 C26 C27 C22 5(3) . . . . ?
C26 N6 C21 N7 3(2) . . . . ?
C27 N7 C21 N6 -4(2) . . . . ?
C27 C22 C23 C24 9(3) . . . . ?
C27 C22 C23 C29 178(2) . . . . ?
C28 C24 C25 C26 174(2) . . . . ?
C29 C23 C24 C25 -178(2) . . . . ?
C29 C23 C24 C28 14(3) . . . . ?

_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_0.64GPa
_database_code_depnum_ccdc_archive 'CCDC 1050861'
_audit_update_record             
;
2015-05-28 deposited with the CCDC.
2015-06-01 downloaded from the CCDC.
;
_audit_creation_date             2015-05-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-4
_chemical_name_common            '5,6-dimethylbenzimidazole phase beta'
_chemical_name_systematic        
;
 5,6-dimethylbenzimidazole phase beta
;
_chemical_formula_moiety         '0.33(C27 H30 N6)'
_chemical_formula_sum            'C9 H10 N2'
_chemical_formula_weight         146.19
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C9 H10 N2'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_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                   6.487(2)
_cell_length_b                   26.63(12)
_cell_length_c                   13.831(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.50(3)
_cell_angle_gamma                90
_cell_volume                     2333(11)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    824
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.2950
_cell_measurement_theta_min      3.2330
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55016
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_special_details           
;
 Data were collected at room temperature and pressure of 0.64(2) GPa
 (640000 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  0.1634
_diffrn_reflns_av_unetI/netI     0.1072
_diffrn_reflns_Laue_measured_fraction_full 0.236
_diffrn_reflns_Laue_measured_fraction_max 0.206
_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       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12153
_diffrn_reflns_point_group_measured_fraction_full 0.236
_diffrn_reflns_point_group_measured_fraction_max 0.206
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.105
_diffrn_reflns_theta_min         3.017
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0772
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.236
_diffrn_measured_fraction_theta_max 0.206
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 phi    -35.00   19.60   0.7000   30.0000
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   30.0000
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   30.0000
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   30.0000
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   30.0000
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   30.0000
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   30.0000
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   30.0000
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   30.0000
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   30.0000
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   30.0000
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   30.0000
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   30.0000
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   30.0000
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   30.0000
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   30.0000
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      -0.0026839000
_diffrn_orient_matrix_UB_12      -0.0266300000
_diffrn_orient_matrix_UB_13      0.0005524000
_diffrn_orient_matrix_UB_21      0.0013482000
_diffrn_orient_matrix_UB_22      0.0004543000
_diffrn_orient_matrix_UB_23      0.0513680000
_diffrn_orient_matrix_UB_31      -0.1120185000
_diffrn_orient_matrix_UB_32      0.0006503000
_diffrn_orient_matrix_UB_33      -0.0107756000
_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                542
_reflns_number_total             1174
_reflns_odcompleteness_completeness 22.17
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.04
_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, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.091
_refine_diff_density_min         -0.098
_refine_diff_density_rms         0.026
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         1174
_refine_ls_number_restraints     501
_refine_ls_R_factor_all          0.1776
_refine_ls_R_factor_gt           0.0730
_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)+(0.1130P)²+0.0130P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1559
_refine_ls_wR_factor_ref         0.2103
_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
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 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 0.008 and
sigma for terminal atoms of 0.01
4. Others
 Fixed Sof: H1(0.5) H3(0.5) H4(0.5) H5(0.5) H6(0.5) H7(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), C2(H2), C4(H4A), C7(H7A), N4(H4), N5(H5), N6(H6), N7(H7),
 C12(H12), C13(H13), C16(H16), C21(H21), C22(H22), C25(H25)
5.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C)
;
_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
N1 N 0.0100(9) 0.1375(7) 0.7202(4) 0.059(4) Uani 1 1 d . U . . .
H1 H 0.0468 0.1409 0.7834 0.071 Uiso 0.5 1 calc R . P . .
N3 N 0.0086(10) 0.1143(8) 0.5675(4) 0.061(4) Uani 1 1 d . U . . .
H3 H 0.0506 0.1003 0.5191 0.073 Uiso 0.5 1 calc R . P . .
C2 C 0.1074(12) 0.1139(11) 0.6636(5) 0.061(4) Uani 1 1 d . U . . .
H2 H 0.2356 0.0977 0.6867 0.073 Uiso 1 1 calc R . . . .
C4 C -0.3394(11) 0.1544(10) 0.4849(5) 0.060(4) Uani 1 1 d . U . . .
H4A H -0.3419 0.1433 0.4209 0.072 Uiso 1 1 calc R . . . .
C5 C -0.5024(12) 0.1837(11) 0.5042(6) 0.068(4) Uani 1 1 d . U . . .
C6 C -0.4961(11) 0.2000(11) 0.6030(6) 0.067(4) Uani 1 1 d . U . . .
C7 C -0.3279(11) 0.1852(10) 0.6775(5) 0.063(4) Uani 1 1 d . U . . .
H7A H -0.3248 0.1951 0.7422 0.076 Uiso 1 1 calc R . . . .
C8 C -0.1654(11) 0.1564(9) 0.6584(5) 0.049(4) Uani 1 1 d . U . . .
C9 C -0.1719(11) 0.1415(9) 0.5622(5) 0.052(4) Uani 1 1 d . U . . .
C10 C -0.6692(11) 0.2337(11) 0.6237(7) 0.096(5) Uani 1 1 d . U . . .
H10A H -0.8005 0.2157 0.6110 0.144 Uiso 1 1 calc GR . . . .
H10B H -0.6820 0.2627 0.5816 0.144 Uiso 1 1 calc GR . . . .
H10C H -0.6348 0.2441 0.6918 0.144 Uiso 1 1 calc GR . . . .
C11 C -0.6790(13) 0.1983(13) 0.4211(7) 0.100(5) Uani 1 1 d . U . . .
H11A H -0.6371 0.1935 0.3593 0.150 Uiso 1 1 calc GR . . . .
H11B H -0.7137 0.2330 0.4279 0.150 Uiso 1 1 calc GR . . . .
H11C H -0.8002 0.1779 0.4225 0.150 Uiso 1 1 calc GR . . . .
N4 N 0.0768(9) 0.0629(8) 0.3990(4) 0.060(4) Uani 1 1 d . U . . .
H4 H 0.1086 0.0696 0.4613 0.073 Uiso 0.5 1 calc R . P . .
N5 N 0.0882(9) 0.0607(8) 0.2420(4) 0.059(4) Uani 1 1 d . U . . .
H5 H 0.1355 0.0645 0.1890 0.070 Uiso 0.5 1 calc R . P . .
N6 N 0.2149(9) 0.0887(8) 0.0721(4) 0.061(4) Uani 1 1 d . U . . .
H6 H 0.1910 0.0729 0.1227 0.073 Uiso 0.5 1 calc R . P . .
N7 N 0.1705(8) 0.1177(7) -0.0806(4) 0.053(4) Uani 1 1 d . U . . .
H7 H 0.1137 0.1228 -0.1420 0.064 Uiso 0.5 1 calc R . P . .
C12 C 0.1823(12) 0.0768(10) 0.3334(6) 0.065(4) Uani 1 1 d . U . . .
H12 H 0.3065 0.0953 0.3477 0.078 Uiso 1 1 calc R . . . .
C13 C -0.2497(12) 0.0112(10) 0.1824(5) 0.063(4) Uani 1 1 d . U . . .
H13 H -0.2429 0.0091 0.1161 0.076 Uiso 1 1 calc R . . . .
C14 C -0.4140(12) -0.0117(10) 0.2144(6) 0.069(4) Uani 1 1 d . U . . .
C15 C -0.4142(12) -0.0088(10) 0.3183(6) 0.072(4) Uani 1 1 d . U . . .
C16 C -0.2586(12) 0.0129(9) 0.3826(5) 0.060(4) Uani 1 1 d . U . . .
H16 H -0.2592 0.0128 0.4498 0.072 Uiso 1 1 calc R . . . .
C17 C -0.0967(11) 0.0354(10) 0.3498(5) 0.052(4) Uani 1 1 d . U . . .
C18 C -0.0929(11) 0.0378(9) 0.2487(5) 0.051(4) Uani 1 1 d . U . . .
C19 C -0.5821(13) -0.0375(12) 0.3577(7) 0.104(5) Uani 1 1 d . U . . .
H19A H -0.7167 -0.0215 0.3353 0.156 Uiso 1 1 calc GR . . . .
H19B H -0.5461 -0.0376 0.4287 0.156 Uiso 1 1 calc GR . . . .
H19C H -0.5892 -0.0714 0.3337 0.156 Uiso 1 1 calc GR . . . .
C20 C -0.5893(13) -0.0399(11) 0.1414(7) 0.096(5) Uani 1 1 d . U . . .
H20A H -0.7242 -0.0259 0.1445 0.144 Uiso 1 1 calc GR . . . .
H20B H -0.5862 -0.0748 0.1590 0.144 Uiso 1 1 calc GR . . . .
H20C H -0.5667 -0.0365 0.0754 0.144 Uiso 1 1 calc GR . . . .
C21 C 0.0934(11) 0.0900(10) -0.0172(5) 0.059(4) Uani 1 1 d . U . . .
H21 H -0.0348 0.0731 -0.0343 0.071 Uiso 1 1 calc R . . . .
C22 C 0.5083(11) 0.1680(9) -0.0562(5) 0.056(4) Uani 1 1 d . U . . .
H22 H 0.4898 0.1789 -0.1214 0.068 Uiso 1 1 calc R . . . .
C23 C 0.6833(11) 0.1826(10) 0.0140(6) 0.064(4) Uani 1 1 d . U . . .
C24 C 0.7097(12) 0.1614(10) 0.1138(6) 0.065(4) Uani 1 1 d . U . . .
C25 C 0.5625(12) 0.1325(10) 0.1381(5) 0.059(4) Uani 1 1 d . U . . .
H25 H 0.5776 0.1221 0.2035 0.071 Uiso 1 1 calc R . . . .
C26 C 0.3857(10) 0.1172(9) 0.0679(4) 0.046(3) Uani 1 1 d . U . . .
C27 C 0.3613(11) 0.1369(9) -0.0284(5) 0.046(4) Uani 1 1 d . U . . .
C28 C 0.8997(12) 0.1826(11) 0.1930(6) 0.085(5) Uani 1 1 d . U . . .
H28A H 0.9018 0.2185 0.1884 0.128 Uiso 1 1 calc GR . . . .
H28B H 1.0295 0.1692 0.1811 0.128 Uiso 1 1 calc GR . . . .
H28C H 0.8845 0.1730 0.2580 0.128 Uiso 1 1 calc GR . . . .
C29 C 0.8470(11) 0.2158(11) -0.0124(6) 0.088(5) Uani 1 1 d . U . . .
H29A H 0.8669 0.2447 0.0302 0.131 Uiso 1 1 calc GR . . . .
H29B H 0.8022 0.2265 -0.0800 0.131 Uiso 1 1 calc GR . . . .
H29C H 0.9776 0.1977 -0.0045 0.131 Uiso 1 1 calc GR . . . .


_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
N1 H1 0.8600 . ?
N1 C2 1.274(16) . ?
N1 C8 1.362(13) . ?
N3 H3 0.8600 . ?
N3 C2 1.345(8) . ?
N3 C9 1.365(17) . ?
C2 H2 0.9300 . ?
C4 H4A 0.9300 . ?
C4 C5 1.39(2) . ?
C4 C9 1.392(12) . ?
C5 C6 1.426(16) . ?
C5 C11 1.488(14) . ?
C6 C7 1.385(13) . ?
C6 C10 1.51(2) . ?
C7 H7A 0.9300 . ?
C7 C8 1.38(2) . ?
C8 C9 1.379(13) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
N4 H4 0.8600 . ?
N4 C12 1.302(12) . ?
N4 C17 1.391(18) . ?
N5 H5 0.8600 . ?
N5 C12 1.349(13) . ?
N5 C18 1.344(15) . ?
N6 H6 0.8600 . ?
N6 C21 1.314(8) . ?
N6 C26 1.355(18) . ?
N7 H7 0.8600 . ?
N7 C21 1.324(17) . ?
N7 C27 1.388(12) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.382(17) . ?
C13 C18 1.404(19) . ?
C14 C15 1.439(10) . ?
C14 C20 1.542(19) . ?
C15 C16 1.325(17) . ?
C15 C19 1.52(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.370(17) . ?
C17 C18 1.405(9) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C22 C23 1.381(13) . ?
C22 C27 1.380(19) . ?
C23 C24 1.468(18) . ?
C23 C29 1.49(2) . ?
C24 C25 1.33(2) . ?
C24 C28 1.566(16) . ?
C25 H25 0.9300 . ?
C25 C26 1.393(13) . ?
C26 C27 1.408(15) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 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
C2 N1 H1 127.6 . . ?
C2 N1 C8 104.7(8) . . ?
C8 N1 H1 127.6 . . ?
C2 N3 H3 127.0 . . ?
C2 N3 C9 106.1(10) . . ?
C9 N3 H3 127.0 . . ?
N1 C2 N3 114.2(11) . . ?
N1 C2 H2 122.9 . . ?
N3 C2 H2 122.9 . . ?
C5 C4 H4A 120.3 . . ?
C5 C4 C9 119.5(10) . . ?
C9 C4 H4A 120.3 . . ?
C4 C5 C6 119.4(10) . . ?
C4 C5 C11 119.4(11) . . ?
C6 C5 C11 121.2(15) . . ?
C5 C6 C10 119.6(10) . . ?
C7 C6 C5 118.8(14) . . ?
C7 C6 C10 121.6(10) . . ?
C6 C7 H7A 119.0 . . ?
C8 C7 C6 121.9(10) . . ?
C8 C7 H7A 119.0 . . ?
N1 C8 C7 131.0(8) . . ?
N1 C8 C9 110.3(12) . . ?
C7 C8 C9 118.7(9) . . ?
N3 C9 C4 133.6(10) . . ?
N3 C9 C8 104.7(8) . . ?
C8 C9 C4 121.7(13) . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C12 N4 H4 126.3 . . ?
C12 N4 C17 107.4(8) . . ?
C17 N4 H4 126.3 . . ?
C12 N5 H5 126.2 . . ?
C18 N5 H5 126.2 . . ?
C18 N5 C12 107.7(8) . . ?
C21 N6 H6 127.0 . . ?
C21 N6 C26 106.0(10) . . ?
C26 N6 H6 127.0 . . ?
C21 N7 H7 126.8 . . ?
C21 N7 C27 106.4(7) . . ?
C27 N7 H7 126.8 . . ?
N4 C12 N5 111.3(12) . . ?
N4 C12 H12 124.3 . . ?
N5 C12 H12 124.3 . . ?
C14 C13 H13 119.5 . . ?
C14 C13 C18 120.9(8) . . ?
C18 C13 H13 119.5 . . ?
C13 C14 C15 117.6(12) . . ?
C13 C14 C20 121.1(8) . . ?
C15 C14 C20 121.3(12) . . ?
C14 C15 C19 119.0(14) . . ?
C16 C15 C14 121.9(12) . . ?
C16 C15 C19 118.6(9) . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.7(8) . . ?
C17 C16 H16 120.1 . . ?
N4 C17 C18 106.0(12) . . ?
C16 C17 N4 131.8(7) . . ?
C16 C17 C18 122.0(11) . . ?
N5 C18 C13 134.7(7) . . ?
N5 C18 C17 107.0(10) . . ?
C13 C18 C17 117.4(13) . . ?
C15 C19 H19A 109.5 . . ?
C15 C19 H19B 109.5 . . ?
C15 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C14 C20 H20A 109.5 . . ?
C14 C20 H20B 109.5 . . ?
C14 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N6 C21 N7 113.7(11) . . ?
N6 C21 H21 123.1 . . ?
N7 C21 H21 123.1 . . ?
C23 C22 H22 120.5 . . ?
C27 C22 H22 120.5 . . ?
C27 C22 C23 119.1(10) . . ?
C22 C23 C24 117.6(15) . . ?
C22 C23 C29 121.2(10) . . ?
C24 C23 C29 121.1(10) . . ?
C23 C24 C28 115.6(16) . . ?
C25 C24 C23 121.3(9) . . ?
C25 C24 C28 122.2(9) . . ?
C24 C25 H25 119.3 . . ?
C24 C25 C26 121.5(9) . . ?
C26 C25 H25 119.3 . . ?
N6 C26 C25 133.7(10) . . ?
N6 C26 C27 108.8(8) . . ?
C25 C26 C27 117.3(13) . . ?
N7 C27 C26 105.1(12) . . ?
C22 C27 N7 131.9(8) . . ?
C22 C27 C26 123.0(9) . . ?
C24 C28 H28A 109.5 . . ?
C24 C28 H28B 109.5 . . ?
C24 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C23 C29 H29A 109.5 . . ?
C23 C29 H29B 109.5 . . ?
C23 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 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(2) . . . . ?
N1 C8 C9 C4 177.7(18) . . . . ?
C2 N1 C8 C7 -180(2) . . . . ?
C2 N1 C8 C9 2(2) . . . . ?
C2 N3 C9 C4 -178(2) . . . . ?
C2 N3 C9 C8 1(2) . . . . ?
C4 C5 C6 C7 -1(3) . . . . ?
C4 C5 C6 C10 177.6(19) . . . . ?
C5 C4 C9 N3 -179(2) . . . . ?
C5 C4 C9 C8 1(3) . . . . ?
C5 C6 C7 C8 1(3) . . . . ?
C6 C7 C8 N1 -179(2) . . . . ?
C6 C7 C8 C9 0(3) . . . . ?
C7 C8 C9 N3 179.6(17) . . . . ?
C7 C8 C9 C4 -1(3) . . . . ?
C8 N1 C2 N3 -1(2) . . . . ?
C9 N3 C2 N1 0(2) . . . . ?
C9 C4 C5 C6 0(3) . . . . ?
C9 C4 C5 C11 179(2) . . . . ?
C10 C6 C7 C8 -177(2) . . . . ?
C11 C5 C6 C7 180(2) . . . . ?
C11 C5 C6 C10 -1(3) . . . . ?
N4 C17 C18 N5 7(2) . . . . ?
N4 C17 C18 C13 177.9(17) . . . . ?
N6 C26 C27 N7 -1(2) . . . . ?
N6 C26 C27 C22 179.4(16) . . . . ?
C12 N4 C17 C16 -179(2) . . . . ?
C12 N4 C17 C18 -5(2) . . . . ?
C12 N5 C18 C13 -175(2) . . . . ?
C12 N5 C18 C17 -6(2) . . . . ?
C13 C14 C15 C16 -3(3) . . . . ?
C13 C14 C15 C19 -174.7(19) . . . . ?
C14 C13 C18 N5 175(2) . . . . ?
C14 C13 C18 C17 7(3) . . . . ?
C14 C15 C16 C17 3(3) . . . . ?
C15 C16 C17 N4 176(2) . . . . ?
C15 C16 C17 C18 2(3) . . . . ?
C16 C17 C18 N5 -178.2(19) . . . . ?
C16 C17 C18 C13 -7(3) . . . . ?
C17 N4 C12 N5 1(2) . . . . ?
C18 N5 C12 N4 3(2) . . . . ?
C18 C13 C14 C15 -2(3) . . . . ?
C18 C13 C14 C20 179(2) . . . . ?
C19 C15 C16 C17 174.8(19) . . . . ?
C20 C14 C15 C16 176(2) . . . . ?
C20 C14 C15 C19 5(3) . . . . ?
C21 N6 C26 C25 176(2) . . . . ?
C21 N6 C26 C27 1(2) . . . . ?
C21 N7 C27 C22 -179.7(19) . . . . ?
C21 N7 C27 C26 0.9(19) . . . . ?
C22 C23 C24 C25 -5(3) . . . . ?
C22 C23 C24 C28 -175.0(17) . . . . ?
C23 C22 C27 N7 177.6(19) . . . . ?
C23 C22 C27 C26 -3(3) . . . . ?
C23 C24 C25 C26 6(3) . . . . ?
C24 C25 C26 N6 -180(2) . . . . ?
C24 C25 C26 C27 -5(3) . . . . ?
C25 C26 C27 N7 -177.2(15) . . . . ?
C25 C26 C27 C22 3(3) . . . . ?
C26 N6 C21 N7 0(2) . . . . ?
C27 N7 C21 N6 0(2) . . . . ?
C27 C22 C23 C24 4(3) . . . . ?
C27 C22 C23 C29 179.6(19) . . . . ?
C28 C24 C25 C26 174.8(19) . . . . ?
C29 C23 C24 C25 179(2) . . . . ?
C29 C23 C24 C28 9(3) . . . . ?

_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_dMBzImH_AP
_database_code_depnum_ccdc_archive 'CCDC 1050862'
_audit_update_record             
;
2015-05-28 deposited with the CCDC.
2015-06-01 downloaded from the CCDC.
;
_audit_creation_date             2015-05-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        Xcalibur
_chemical_formula_moiety         '0.25(H4 O4), 2(C9 H10 N2)'
_chemical_formula_sum            'C18 H21 N4 O'
_chemical_formula_weight         309.39
_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      orthorhombic
_space_group_IT_number           70
_space_group_name_H-M_alt        'F d d d'
_space_group_name_Hall           '-F 2uv 2vw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/4, -y+1/4, z'
'x, -y+1/4, -z+1/4'
'-x+1/4, y, -z+1/4'
'x, y+1/2, z+1/2'
'-x+1/4, -y+3/4, z+1/2'
'x, -y+3/4, -z+3/4'
'-x+1/4, y+1/2, -z+3/4'
'x+1/2, y, z+1/2'
'-x+3/4, -y+1/4, z+1/2'
'x+1/2, -y+1/4, -z+3/4'
'-x+3/4, y, -z+3/4'
'x+1/2, y+1/2, z'
'-x+3/4, -y+3/4, z'
'x+1/2, -y+3/4, -z+1/4'
'-x+3/4, y+1/2, -z+1/4'
'-x, -y, -z'
'x-1/4, y-1/4, -z'
'-x, y-1/4, z-1/4'
'x-1/4, -y, z-1/4'
'-x, -y+1/2, -z+1/2'
'x-1/4, y+1/4, -z+1/2'
'-x, y+1/4, z+1/4'
'x-1/4, -y+1/2, z+1/4'
'-x+1/2, -y, -z+1/2'
'x+1/4, y-1/4, -z+1/2'
'-x+1/2, y-1/4, z+1/4'
'x+1/4, -y, z+1/4'
'-x+1/2, -y+1/2, -z'
'x+1/4, y+1/4, -z'
'-x+1/2, y+1/4, z-1/4'
'x+1/4, -y+1/2, z-1/4'

_cell_length_a                   7.5684(10)
_cell_length_b                   12.432(2)
_cell_length_c                   34.803(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3274.5(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    614
_cell_measurement_temperature    296
_cell_measurement_theta_max      19.8710
_cell_measurement_theta_min      4.6730
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67919
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    ?
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1320
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1387
_diffrn_reflns_av_unetI/netI     0.1362
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            3718
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.522
_diffrn_reflns_theta_min         4.302
_diffrn_ambient_temperature      296
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2413
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -92.00  -66.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -        1.7187 -178.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -73.00  -45.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -        1.7187 -178.0000 -180.0000 28

#__ type_ start__ end____ width___ exp.time_
  3 omega  -63.00  -37.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -        1.7187 -178.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  -18.00   45.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      -27.7209   77.0000   30.0000 63

#__ type_ start__ end____ width___ exp.time_
  5 omega -118.00  -92.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      -27.7209  -99.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega  -49.00   56.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -       31.1584  -38.0000  150.0000 105

#__ type_ start__ end____ width___ exp.time_
  7 omega -103.00  -35.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -        1.7187 -178.0000 -120.0000 68

#__ type_ start__ end____ width___ exp.time_
  8 omega  -47.00   92.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -        1.7187   61.0000  -62.0000 139

#__ type_ start__ end____ width___ exp.time_
  9 omega  -20.00  121.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -       31.1584   77.0000   90.0000 141
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0039645000
_diffrn_orient_matrix_UB_12      -0.0407343000
_diffrn_orient_matrix_UB_13      0.0142343000
_diffrn_orient_matrix_UB_21      -0.0317546000
_diffrn_orient_matrix_UB_22      0.0369330000
_diffrn_orient_matrix_UB_23      0.0139297000
_diffrn_orient_matrix_UB_31      -0.0880518000
_diffrn_orient_matrix_UB_32      -0.0151858000
_diffrn_orient_matrix_UB_33      -0.0043740000
_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          
'Data were collected at room temperature and pressure with the crystal obtained in high-pressure experiment.'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                389
_reflns_number_total             798
_reflns_odcompleteness_completeness 99.65
_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, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     58
_refine_ls_number_reflns         798
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1719
_refine_ls_R_factor_gt           0.0772
_refine_ls_restrained_S_all      1.077
_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)+(0.0633P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1504
_refine_ls_wR_factor_ref         0.1999
_refine_special_details          
;
Correction for absorption of the diamond-anvil cell and the sample 
 were made using program REDSHABS (Katrusiak, A. (2003) REDSHABS. Adam
 Mickiewicz University Poznań; Katrusiak, A. (2004) Z. Kristallogr.
 219, 461-467).
;
_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. Others
 Fixed Sof: H1(0.25) H3(0.5)
3.a Free rotating group:
 O1(H1)
3.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C2(H2), C4(H4)
3.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_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 -0.1250 0.3750 0.3750 0.0523(13) Uani 1 4 d S T P . .
H1 H -0.0481 0.4005 0.3597 0.078 Uiso 0.25 1 d G . . . .
N3 N 0.0373(4) 0.5524(2) 0.33615(7) 0.0528(10) Uani 1 1 d . . . . .
H3 H -0.0256 0.4997 0.3445 0.063 Uiso 0.5 1 calc R . . . .
C2 C 0.1250 0.6250 0.35668(14) 0.0594(15) Uani 1 2 d S T P . .
H2 H 0.1250 0.6250 0.3834 0.071 Uiso 1 2 calc RS T P . .
C4 C 0.0100(4) 0.5367(2) 0.26414(9) 0.0450(10) Uani 1 1 d . . . . .
H4 H -0.0668 0.4783 0.2643 0.054 Uiso 1 1 calc R . . . .
C5 C 0.0658(4) 0.5809(2) 0.22993(8) 0.0427(10) Uani 1 1 d . . . . .
C9 C 0.0696(4) 0.5805(2) 0.29833(8) 0.0404(9) Uani 1 1 d . . . . .
C10 C -0.0028(5) 0.5354(3) 0.19265(9) 0.0668(13) Uani 1 1 d . . . . .
H10A H -0.0670 0.5900 0.1790 0.100 Uiso 1 1 calc GR . . . .
H10B H -0.0798 0.4758 0.1980 0.100 Uiso 1 1 calc GR . . . .
H10C H 0.0946 0.5113 0.1772 0.100 Uiso 1 1 calc GR . . . .


_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 0.8499 . ?
N3 H3 0.8600 . ?
N3 C2 1.329(3) . ?
N3 C9 1.384(4) . ?
C2 N3 1.329(3) 2_565 ?
C2 H2 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.377(4) . ?
C4 C9 1.384(4) . ?
C5 C5 1.416(6) 2_565 ?
C5 C10 1.508(4) . ?
C9 C9 1.388(5) 2_565 ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 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
C2 N3 H3 127.7 . . ?
C2 N3 C9 104.6(3) . . ?
C9 N3 H3 127.7 . . ?
N3 C2 N3 115.0(4) . 2_565 ?
N3 C2 H2 122.5 2_565 . ?
N3 C2 H2 122.5 . . ?
C5 C4 H4 120.4 . . ?
C5 C4 C9 119.1(3) . . ?
C9 C4 H4 120.4 . . ?
C4 C5 C5 120.18(17) . 2_565 ?
C4 C5 C10 119.2(3) . . ?
C5 C5 C10 120.57(19) 2_565 . ?
N3 C9 C4 131.4(3) . . ?
N3 C9 C9 107.95(16) . 2_565 ?
C4 C9 C9 120.68(19) . 2_565 ?
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 . . ?

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
C2 N3 C9 C4 -178.0(3) . . . . ?
C2 N3 C9 C9 1.1(4) . . . 2_565 ?
C5 C4 C9 N3 -179.3(3) . . . . ?
C5 C4 C9 C9 1.7(5) . . . 2_565 ?
C9 N3 C2 N3 -0.42(14) . . . 2_565 ?
C9 C4 C5 C5 0.7(5) . . . 2_565 ?
C9 C4 C5 C10 -178.3(3) . . . . ?

_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_dMBzImH_0.54GPa
_database_code_depnum_ccdc_archive 'CCDC 1050863'
_audit_update_record             
;
2015-05-28 deposited with the CCDC.
2015-06-01 downloaded from the CCDC.
;
_audit_creation_date             2015-05-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-4
_chemical_name_common            '5,6-dimethylbenzimidazole hemihydrate'
_chemical_name_systematic        
;
 5,6-dimethylbenzimidazole hemihydrate
;
_chemical_formula_moiety         '0.25(H4 O4), 2(C9 H10 N2)'
_chemical_formula_sum            'C18 H21 N4 O'
_chemical_formula_weight         309.39
_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      orthorhombic
_space_group_IT_number           70
_space_group_name_H-M_alt        'F d d d'
_space_group_name_Hall           '-F 2uv 2vw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/4, -y+1/4, z'
'x, -y+1/4, -z+1/4'
'-x+1/4, y, -z+1/4'
'x, y+1/2, z+1/2'
'-x+1/4, -y+3/4, z+1/2'
'x, -y+3/4, -z+3/4'
'-x+1/4, y+1/2, -z+3/4'
'x+1/2, y, z+1/2'
'-x+3/4, -y+1/4, z+1/2'
'x+1/2, -y+1/4, -z+3/4'
'-x+3/4, y, -z+3/4'
'x+1/2, y+1/2, z'
'-x+3/4, -y+3/4, z'
'x+1/2, -y+3/4, -z+1/4'
'-x+3/4, y+1/2, -z+1/4'
'-x, -y, -z'
'x-1/4, y-1/4, -z'
'-x, y-1/4, z-1/4'
'x-1/4, -y, z-1/4'
'-x, -y+1/2, -z+1/2'
'x-1/4, y+1/4, -z+1/2'
'-x, y+1/4, z+1/4'
'x-1/4, -y+1/2, z+1/4'
'-x+1/2, -y, -z+1/2'
'x+1/4, y-1/4, -z+1/2'
'-x+1/2, y-1/4, z+1/4'
'x+1/4, -y, z+1/4'
'-x+1/2, -y+1/2, -z'
'x+1/4, y+1/4, -z'
'-x+1/2, y+1/4, z-1/4'
'x+1/4, -y+1/2, z-1/4'

_cell_length_a                   7.2661(15)
_cell_length_b                   12.407(8)
_cell_length_c                   34.550(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3115(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    710
_cell_measurement_temperature    296
_cell_measurement_theta_max      24.8040
_cell_measurement_theta_min      3.7370
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
Correction for absorption of the diamond-anvil cell and the sample 
 were made using program REDSHABS (Katrusiak, A. (2003) REDSHABS. Adam
 Mickiewicz University Poznań; Katrusiak, A. (2004) Z. Kristallogr.
 219, 461-467).
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_special_details           
;
 Data were collected at room temperature and pressure of 0.54(2) GPa
 (540000 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  0.1459
_diffrn_reflns_av_unetI/netI     0.0846
_diffrn_reflns_Laue_measured_fraction_full 0.599
_diffrn_reflns_Laue_measured_fraction_max 0.555
_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       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            3831
_diffrn_reflns_point_group_measured_fraction_full 0.599
_diffrn_reflns_point_group_measured_fraction_max 0.555
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.160
_diffrn_reflns_theta_min         4.389
_diffrn_ambient_temperature      296
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2413
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.599
_diffrn_measured_fraction_theta_max 0.555
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 phi    -35.00   19.60   0.7000   10.0000
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   10.0000
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   10.0000
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   10.0000
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   10.0000
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   10.0000
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   10.0000
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   10.0000
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   10.0000
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   10.0000
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   10.0000
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   10.0000
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   10.0000
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   10.0000
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   10.0000
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   10.0000
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      -0.0293014000
_diffrn_orient_matrix_UB_12      -0.0510425000
_diffrn_orient_matrix_UB_13      0.0069777000
_diffrn_orient_matrix_UB_21      0.0020631000
_diffrn_orient_matrix_UB_22      0.0199786000
_diffrn_orient_matrix_UB_23      0.0192113000
_diffrn_orient_matrix_UB_31      -0.0930107000
_diffrn_orient_matrix_UB_32      0.0164967000
_diffrn_orient_matrix_UB_33      -0.0017600000
_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                254
_reflns_number_total             486
_reflns_odcompleteness_completeness 54.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.10
_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, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     58
_refine_ls_number_reflns         486
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.1586
_refine_ls_R_factor_gt           0.0848
_refine_ls_restrained_S_all      1.011
_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)+(0.1580P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2067
_refine_ls_wR_factor_ref         0.2753
_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. Restrained distances
 H1-N3
 1.98 with sigma of 0.001
3. 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
4. Uiso/Uaniso restraints and constraints
O1: within 1.7A with sigma of 0.1 and sigma for terminal atoms of 0.08
Uanis(O1) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
5. Others
 Fixed Sof: H1(0.25) H3(0.5)
6.a Free rotating group:
 O1(H1)
6.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C2(H2), C4(H4)
6.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_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 -0.1250 0.3750 0.3750 0.062(3) Uani 1 4 d S TU P . .
H1 H -0.0469 0.4213 0.3639 0.093 Uiso 0.25 1 d DG . . . .
N3 N 0.0343(5) 0.5519(4) 0.33575(9) 0.061(2) Uani 1 1 d D U . . .
H3 H -0.0304 0.4987 0.3442 0.073 Uiso 0.5 1 calc R . . . .
C2 C 0.1250 0.6250 0.35629(18) 0.067(3) Uani 1 2 d S TU P . .
H2 H 0.1250 0.6250 0.3832 0.081 Uiso 1 2 calc RS T P . .
C4 C 0.0056(6) 0.5350(5) 0.26279(10) 0.055(3) Uani 1 1 d . U . . .
H4 H -0.0736 0.4761 0.2631 0.066 Uiso 1 1 calc R . . . .
C5 C 0.0642(6) 0.5790(5) 0.22848(11) 0.053(2) Uani 1 1 d . U . . .
C9 C 0.0681(5) 0.5811(6) 0.29712(11) 0.051(2) Uani 1 1 d . U . . .
C10 C -0.0071(7) 0.5342(5) 0.19075(11) 0.073(3) Uani 1 1 d . U . . .
H10A H -0.0763 0.5888 0.1775 0.110 Uiso 1 1 calc GR . . . .
H10B H -0.0851 0.4734 0.1959 0.110 Uiso 1 1 calc GR . . . .
H10C H 0.0946 0.5120 0.1749 0.110 Uiso 1 1 calc GR . . . .


_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 0.8935 . ?
N3 H3 0.8600 . ?
N3 C2 1.327(5) . ?
N3 C9 1.405(5) . ?
C2 N3 1.327(5) 2_565 ?
C2 H2 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.373(5) . ?
C4 C9 1.393(6) . ?
C5 C5 1.443(11) 2_565 ?
C5 C10 1.509(5) . ?
C9 C9 1.367(12) 2_565 ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 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
C2 N3 H3 127.9 . . ?
C2 N3 C9 104.2(5) . . ?
C9 N3 H3 127.9 . . ?
N3 C2 N3 115.3(6) . 2_565 ?
N3 C2 H2 122.3 2_565 . ?
N3 C2 H2 122.3 . . ?
C5 C4 H4 121.0 . . ?
C5 C4 C9 118.1(6) . . ?
C9 C4 H4 121.0 . . ?
C4 C5 C5 120.3(3) . 2_565 ?
C4 C5 C10 119.5(5) . . ?
C5 C5 C10 120.1(3) 2_565 . ?
C4 C9 N3 130.2(5) . . ?
C9 C9 N3 108.2(3) 2_565 . ?
C9 C9 C4 121.6(3) 2_565 . ?
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 . . ?

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
C2 N3 C9 C4 -178.7(5) . . . . ?
C2 N3 C9 C9 1.7(7) . . . 2_565 ?
C5 C4 C9 N3 -178.5(5) . . . . ?
C5 C4 C9 C9 1.1(10) . . . 2_565 ?
C9 N3 C2 N3 -0.6(2) . . . 2_565 ?
C9 C4 C5 C5 -0.5(9) . . . 2_565 ?
C9 C4 C5 C10 -177.4(4) . . . . ?

_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_dMBzImH_0.70GPa
_database_code_depnum_ccdc_archive 'CCDC 1050864'
_audit_update_record             
;
2015-05-28 deposited with the CCDC.
2015-06-01 downloaded from the CCDC.
;
_audit_creation_date             2015-05-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-4
_chemical_name_common            '5,6-dimethylbenzimidazole hemihydrate'
_chemical_name_systematic        
;
 5,6-dimethylbenzimidazole hemihydrate
;
_chemical_formula_moiety         '0.5(C36 H42 N8 O2)'
_chemical_formula_sum            'C18 H21 N4 O'
_chemical_formula_weight         309.39
_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 0.0015 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      orthorhombic
_space_group_IT_number           70
_space_group_name_H-M_alt        'F d d d'
_space_group_name_Hall           '-F 2uv 2vw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/4, -y+1/4, z'
'x, -y+1/4, -z+1/4'
'-x+1/4, y, -z+1/4'
'x, y+1/2, z+1/2'
'-x+1/4, -y+3/4, z+1/2'
'x, -y+3/4, -z+3/4'
'-x+1/4, y+1/2, -z+3/4'
'x+1/2, y, z+1/2'
'-x+3/4, -y+1/4, z+1/2'
'x+1/2, -y+1/4, -z+3/4'
'-x+3/4, y, -z+3/4'
'x+1/2, y+1/2, z'
'-x+3/4, -y+3/4, z'
'x+1/2, -y+3/4, -z+1/4'
'-x+3/4, y+1/2, -z+1/4'
'-x, -y, -z'
'x-1/4, y-1/4, -z'
'-x, y-1/4, z-1/4'
'x-1/4, -y, z-1/4'
'-x, -y+1/2, -z+1/2'
'x-1/4, y+1/4, -z+1/2'
'-x, y+1/4, z+1/4'
'x-1/4, -y+1/2, z+1/4'
'-x+1/2, -y, -z+1/2'
'x+1/4, y-1/4, -z+1/2'
'-x+1/2, y-1/4, z+1/4'
'x+1/4, -y, z+1/4'
'-x+1/2, -y+1/2, -z'
'x+1/4, y+1/4, -z'
'-x+1/2, y+1/4, z-1/4'
'x+1/4, -y+1/2, z-1/4'

_cell_length_a                   7.173(3)
_cell_length_b                   12.383(5)
_cell_length_c                   34.439(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3059.0(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    649
_cell_measurement_temperature    296
_cell_measurement_theta_max      19.2350
_cell_measurement_theta_min      6.3520
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.055
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
 Correction for absorption of the diamond-anvil cell and the sample 
 were made using program REDSHABS (Katrusiak, A. (2003) REDSHABS. Adam
 Mickiewicz University Poznań; Katrusiak, A. (2004) Z. Kristallogr.
 219, 461-467).
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_special_details           
;
 Data were collected at room temperature and pressure of 0.70(2) GPa
 (700000 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  0.2197
_diffrn_reflns_av_unetI/netI     0.1515
_diffrn_reflns_Laue_measured_fraction_full 0.603
_diffrn_reflns_Laue_measured_fraction_max 0.516
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_number            5885
_diffrn_reflns_point_group_measured_fraction_full 0.603
_diffrn_reflns_point_group_measured_fraction_max 0.516
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         24.692
_diffrn_reflns_theta_min         6.396
_diffrn_ambient_temperature      296
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0593
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.603
_diffrn_measured_fraction_theta_max 0.516
_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  -24.00   24.00   0.7500   35.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   39.4600  -12.9000 64

#__ type_ start__ end____ width___ exp.time_
  6 omega  -24.00   24.00   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  -19.00    8.00   0.7500   35.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   81.4000  151.1000 36

#__ type_ start__ end____ width___ exp.time_
 12 omega  -19.00    8.00   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      0.0566287000
_diffrn_orient_matrix_UB_12      0.0307991000
_diffrn_orient_matrix_UB_13      0.0016912000
_diffrn_orient_matrix_UB_21      0.0171634000
_diffrn_orient_matrix_UB_22      -0.0038371000
_diffrn_orient_matrix_UB_23      -0.0157698000
_diffrn_orient_matrix_UB_31      -0.0508282000
_diffrn_orient_matrix_UB_32      0.0328447000
_diffrn_orient_matrix_UB_33      -0.0034480000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56087
_diffrn_source                   'Enhance (Ag) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                299
_reflns_number_total             693
_reflns_odcompleteness_completeness 50.36
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.62
_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, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     58
_refine_ls_number_reflns         693
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2145
_refine_ls_R_factor_gt           0.0933
_refine_ls_restrained_S_all      1.013
_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)+(0.1360P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2169
_refine_ls_wR_factor_ref         0.2891
_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. Restrained distances
 H1-N3
 1.974 with sigma of 0.0001
3. Others
 Fixed Sof: H1(0.25) H3(0.5)
4.a Free rotating group:
 O1(H1)
4.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C2(H2), C4(H4)
4.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_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 -0.1250 0.3750 0.3750 0.0470(17) Uani 1 4 d S T P . .
H1 H -0.0884 0.4285 0.3615 0.071 Uiso 0.25 1 d DG . . . .
N3 N 0.0334(5) 0.5520(2) 0.33561(7) 0.0469(12) Uani 1 1 d D . . . .
H3 H -0.0325 0.4989 0.3441 0.056 Uiso 0.5 1 calc R . . . .
C2 C 0.1250 0.6250 0.35614(16) 0.0526(19) Uani 1 2 d S T P . .
H2 H 0.1250 0.6250 0.3831 0.063 Uiso 1 2 calc RS T P . .
C4 C 0.0039(6) 0.5349(3) 0.26237(8) 0.0422(12) Uani 1 1 d . . . . .
H4 H -0.0761 0.4758 0.2627 0.051 Uiso 1 1 calc R . . . .
C5 C 0.0617(8) 0.5792(3) 0.22789(9) 0.0418(13) Uani 1 1 d . . . . .
C9 C 0.0680(9) 0.5808(4) 0.29675(9) 0.0415(13) Uani 1 1 d . . . . .
C10 C -0.0092(8) 0.5344(4) 0.19028(10) 0.0588(15) Uani 1 1 d . . . . .
H10A H -0.0689 0.5907 0.1757 0.088 Uiso 1 1 calc GR . . . .
H10B H -0.0972 0.4778 0.1954 0.088 Uiso 1 1 calc GR . . . .
H10C H 0.0933 0.5059 0.1756 0.088 Uiso 1 1 calc GR . . . .


_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 0.8504 . ?
N3 H3 0.8600 . ?
N3 C2 1.323(4) . ?
N3 C9 1.407(4) . ?
C2 N3 1.323(4) 2_565 ?
C2 H2 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.372(5) . ?
C4 C9 1.391(5) . ?
C5 C5 1.453(10) 2_565 ?
C5 C10 1.498(6) . ?
C9 C9 1.367(10) 2_565 ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 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
C2 N3 H3 127.8 . . ?
C2 N3 C9 104.3(3) . . ?
C9 N3 H3 127.8 . . ?
N3 C2 N3 115.4(4) 2_565 . ?
N3 C2 H2 122.3 . . ?
N3 C2 H2 122.3 2_565 . ?
C5 C4 H4 120.9 . . ?
C5 C4 C9 118.3(4) . . ?
C9 C4 H4 120.9 . . ?
C4 C5 C5 120.1(2) . 2_565 ?
C4 C5 C10 119.8(4) . . ?
C5 C5 C10 120.1(3) 2_565 . ?
C4 C9 N3 130.4(4) . . ?
C9 C9 N3 108.0(2) 2_565 . ?
C9 C9 C4 121.7(3) 2_565 . ?
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 . . ?

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
C2 N3 C9 C4 -178.2(5) . . . . ?
C2 N3 C9 C9 1.0(7) . . . 2_565 ?
C5 C4 C9 N3 -179.4(5) . . . . ?
C5 C4 C9 C9 1.5(10) . . . 2_565 ?
C9 N3 C2 N3 -0.4(3) . . . 2_565 ?
C9 C4 C5 C5 0.7(8) . . . 2_565 ?
C9 C4 C5 C10 -178.0(5) . . . . ?

_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_dMBzImH_1.10GPa
_database_code_depnum_ccdc_archive 'CCDC 1050865'
_audit_update_record             
;
2015-05-28 deposited with the CCDC.
2015-06-01 downloaded from the CCDC.
;
_audit_creation_date             2015-05-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-4
_chemical_name_common            '5,6-dimethylbenzimidazole hemihydrate'
_chemical_name_systematic        
;
 5,6-dimethylbenzimidazole hemihydrate
;
_chemical_formula_moiety         '0.25(H4 O4), 2(C9 H10 N2)'
_chemical_formula_sum            'C18 H21 N4 O'
_chemical_formula_weight         309.39
_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      orthorhombic
_space_group_IT_number           70
_space_group_name_H-M_alt        'F d d d'
_space_group_name_Hall           '-F 2uv 2vw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/4, -y+1/4, z'
'x, -y+1/4, -z+1/4'
'-x+1/4, y, -z+1/4'
'x, y+1/2, z+1/2'
'-x+1/4, -y+3/4, z+1/2'
'x, -y+3/4, -z+3/4'
'-x+1/4, y+1/2, -z+3/4'
'x+1/2, y, z+1/2'
'-x+3/4, -y+1/4, z+1/2'
'x+1/2, -y+1/4, -z+3/4'
'-x+3/4, y, -z+3/4'
'x+1/2, y+1/2, z'
'-x+3/4, -y+3/4, z'
'x+1/2, -y+3/4, -z+1/4'
'-x+3/4, y+1/2, -z+1/4'
'-x, -y, -z'
'x-1/4, y-1/4, -z'
'-x, y-1/4, z-1/4'
'x-1/4, -y, z-1/4'
'-x, -y+1/2, -z+1/2'
'x-1/4, y+1/4, -z+1/2'
'-x, y+1/4, z+1/4'
'x-1/4, -y+1/2, z+1/4'
'-x+1/2, -y, -z+1/2'
'x+1/4, y-1/4, -z+1/2'
'-x+1/2, y-1/4, z+1/4'
'x+1/4, -y, z+1/4'
'-x+1/2, -y+1/2, -z'
'x+1/4, y+1/4, -z'
'-x+1/2, y+1/4, z-1/4'
'x+1/4, -y+1/2, z-1/4'

_cell_length_a                   7.040(2)
_cell_length_b                   12.334(4)
_cell_length_c                   34.323(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2980.3(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    740
_cell_measurement_temperature    296
_cell_measurement_theta_max      19.2250
_cell_measurement_theta_min      3.7650
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
 Correction for absorption of the diamond-anvil cell and the sample 
 were made using program REDSHABS (Katrusiak, A. (2003) REDSHABS. Adam
 Mickiewicz University Poznań; Katrusiak, A. (2004) Z. Kristallogr.
 219, 461-467).
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_special_details           
;
 Data were collected at room temperature and pressure of 1.10(2) GPa
 (1100000 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  0.1106
_diffrn_reflns_av_unetI/netI     0.0659
_diffrn_reflns_Laue_measured_fraction_full 0.508
_diffrn_reflns_Laue_measured_fraction_max 0.468
_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       44
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            3870
_diffrn_reflns_point_group_measured_fraction_full 0.508
_diffrn_reflns_point_group_measured_fraction_max 0.468
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.375
_diffrn_reflns_theta_min         3.779
_diffrn_ambient_temperature      296
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2413
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.508
_diffrn_measured_fraction_theta_max 0.468
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 phi    -35.00   19.75   0.7500   32.0000
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   32.0000
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   32.0000
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   32.0000
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   32.0000
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   32.0000
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   32.0000
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   32.0000
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   32.0000
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   32.0000
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   32.0000
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   32.0000
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   32.0000
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   32.0000
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   32.0000
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   32.0000
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      0.0732683000
_diffrn_orient_matrix_UB_12      -0.0392837000
_diffrn_orient_matrix_UB_13      -0.0012883000
_diffrn_orient_matrix_UB_21      0.0173499000
_diffrn_orient_matrix_UB_22      0.0052902000
_diffrn_orient_matrix_UB_23      0.0202673000
_diffrn_orient_matrix_UB_31      -0.0669543000
_diffrn_orient_matrix_UB_32      -0.0416944000
_diffrn_orient_matrix_UB_33      0.0038307000
_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                231
_reflns_number_total             398
_reflns_odcompleteness_completeness 44.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.31
_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, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.0022(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     59
_refine_ls_number_reflns         398
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1290
_refine_ls_R_factor_gt           0.0696
_refine_ls_restrained_S_all      1.028
_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)+(0.1373P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1817
_refine_ls_wR_factor_ref         0.2223
_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. Restrained distances
 H1-N3
 2.1 with sigma of 0.02
3. Others
 Fixed Sof: H1(0.25) H3(0.5)
4.a Free rotating group:
 O1(H1)
4.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C2(H2), C4(H4)
4.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_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 -0.1250 -0.1250 0.3750 0.0420(19) Uani 1 4 d S T P . .
H1 H -0.0677 -0.0991 0.3553 0.063 Uiso 0.25 1 d DG . . . .
N3 N 0.0328(7) 0.0511(3) 0.33529(8) 0.0436(15) Uani 1 1 d D . . . .
H3 H -0.0321 -0.0031 0.3438 0.052 Uiso 0.5 1 calc R . . . .
C2 C 0.1250 0.1250 0.35630(16) 0.051(2) Uani 1 2 d S T P . .
H2 H 0.1250 0.1250 0.3834 0.061 Uiso 1 2 calc RS T P . .
C4 C 0.0024(7) 0.0340(4) 0.26197(9) 0.0365(15) Uani 1 1 d . . . . .
H4 H -0.0781 -0.0257 0.2621 0.044 Uiso 1 1 calc R . . . .
C5 C 0.0643(10) 0.0793(4) 0.22725(10) 0.0365(15) Uani 1 1 d . . . . .
C9 C 0.0640(11) 0.0805(5) 0.29665(9) 0.0357(16) Uani 1 1 d . . . . .
C10 C -0.0131(8) 0.0335(4) 0.18941(10) 0.0531(19) Uani 1 1 d . . . . .
H10A H -0.0853 0.0883 0.1762 0.080 Uiso 1 1 calc GR . . . .
H10B H -0.0934 -0.0275 0.1949 0.080 Uiso 1 1 calc GR . . . .
H10C H 0.0905 0.0107 0.1732 0.080 Uiso 1 1 calc GR . . . .


_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 0.8501 . ?
N3 H3 0.8600 . ?
N3 C2 1.332(4) . ?
N3 C9 1.392(4) . ?
C2 N3 1.332(4) 2 ?
C2 H2 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.386(5) . ?
C4 C9 1.390(5) . ?
C5 C5 1.415(10) 2 ?
C5 C10 1.518(5) . ?
C9 C9 1.394(10) 2 ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 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
C2 N3 H3 127.5 . . ?
C2 N3 C9 105.1(4) . . ?
C9 N3 H3 127.5 . . ?
N3 C2 N3 114.4(5) 2 . ?
N3 C2 H2 122.8 . . ?
N3 C2 H2 122.8 2 . ?
C5 C4 H4 120.9 . . ?
C5 C4 C9 118.2(5) . . ?
C9 C4 H4 120.9 . . ?
C4 C5 C5 120.7(2) . 2 ?
C4 C5 C10 118.2(4) . . ?
C5 C5 C10 120.9(3) 2 . ?
N3 C9 C9 107.6(3) . 2 ?
C4 C9 N3 131.2(4) . . ?
C4 C9 C9 121.1(3) . 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 . . ?

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
C2 N3 C9 C4 -179.7(8) . . . . ?
C2 N3 C9 C9 3.5(10) . . . 2 ?
C5 C4 C9 N3 -177.1(7) . . . . ?
C5 C4 C9 C9 -0.6(14) . . . 2 ?
C9 N3 C2 N3 -1.4(4) . . . 2 ?
C9 C4 C5 C5 -0.5(12) . . . 2 ?
C9 C4 C5 C10 -176.0(6) . . . . ?

_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_dMBzImH_1.49GPa
_database_code_depnum_ccdc_archive 'CCDC 1050866'
_audit_update_record             
;
2015-05-28 deposited with the CCDC.
2015-06-01 downloaded from the CCDC.
;
_audit_creation_date             2015-05-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-4
_chemical_name_common            '5,6-dimethylbenzimidazole hemihydrate'
_chemical_name_systematic        
;
 5,6-dimethylbenzimidazole hemihydrate
;
_chemical_formula_moiety         '0.25(H4 O4), 2(C9 H10 N2)'
_chemical_formula_sum            'C18 H21 N4 O'
_chemical_formula_weight         309.39
_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      orthorhombic
_space_group_IT_number           70
_space_group_name_H-M_alt        'F d d d'
_space_group_name_Hall           '-F 2uv 2vw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/4, -y+1/4, z'
'x, -y+1/4, -z+1/4'
'-x+1/4, y, -z+1/4'
'x, y+1/2, z+1/2'
'-x+1/4, -y+3/4, z+1/2'
'x, -y+3/4, -z+3/4'
'-x+1/4, y+1/2, -z+3/4'
'x+1/2, y, z+1/2'
'-x+3/4, -y+1/4, z+1/2'
'x+1/2, -y+1/4, -z+3/4'
'-x+3/4, y, -z+3/4'
'x+1/2, y+1/2, z'
'-x+3/4, -y+3/4, z'
'x+1/2, -y+3/4, -z+1/4'
'-x+3/4, y+1/2, -z+1/4'
'-x, -y, -z'
'x-1/4, y-1/4, -z'
'-x, y-1/4, z-1/4'
'x-1/4, -y, z-1/4'
'-x, -y+1/2, -z+1/2'
'x-1/4, y+1/4, -z+1/2'
'-x, y+1/4, z+1/4'
'x-1/4, -y+1/2, z+1/4'
'-x+1/2, -y, -z+1/2'
'x+1/4, y-1/4, -z+1/2'
'-x+1/2, y-1/4, z+1/4'
'x+1/4, -y, z+1/4'
'-x+1/2, -y+1/2, -z'
'x+1/4, y+1/4, -z'
'-x+1/2, y+1/4, z-1/4'
'x+1/4, -y+1/2, z-1/4'

_cell_length_a                   6.9376(16)
_cell_length_b                   12.228(3)
_cell_length_c                   34.174(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2899.1(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1257
_cell_measurement_temperature    296
_cell_measurement_theta_max      25.5180
_cell_measurement_theta_min      3.4130
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.05743
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_special_details           
;
 Data were collected at room temperature and pressure of 1.49(2) GPa
 (1490000 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  0.0826
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_Laue_measured_fraction_full 0.524
_diffrn_reflns_Laue_measured_fraction_max 0.470
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            4816
_diffrn_reflns_point_group_measured_fraction_full 0.524
_diffrn_reflns_point_group_measured_fraction_max 0.470
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.140
_diffrn_reflns_theta_min         3.429
_diffrn_ambient_temperature      296
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1544
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.524
_diffrn_measured_fraction_theta_max 0.470
_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      0.0743475000
_diffrn_orient_matrix_UB_12      0.0397618000
_diffrn_orient_matrix_UB_13      0.0007886000
_diffrn_orient_matrix_UB_21      0.0194800000
_diffrn_orient_matrix_UB_22      -0.0085736000
_diffrn_orient_matrix_UB_23      -0.0201493000
_diffrn_orient_matrix_UB_31      -0.0675484000
_diffrn_orient_matrix_UB_32      0.0412621000
_diffrn_orient_matrix_UB_33      -0.0049416000
_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                273
_reflns_number_total             421
_reflns_odcompleteness_completeness 45.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.08
_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, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     58
_refine_ls_number_reflns         421
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1104
_refine_ls_R_factor_gt           0.0698
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1170P)²+6.9350P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1839
_refine_ls_wR_factor_ref         0.2223
_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. Others
 Fixed Sof: H1(0.25) H3(0.5)
3.a Free rotating group:
 O1(H1)
3.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C2(H2), C4(H4)
3.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_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 -0.1250 0.3750 0.3750 0.0388(17) Uani 1 4 d S T P . .
H1 H -0.0706 0.3387 0.3931 0.058 Uiso 0.25 1 d G . . . .
N3 N 0.0319(6) 0.1993(3) 0.41485(8) 0.0389(12) Uani 1 1 d . . . . .
H3 H -0.0344 0.2539 0.4064 0.047 Uiso 0.5 1 calc R . . . .
C2 C 0.1250 0.1250 0.39370(14) 0.0467(19) Uani 1 2 d S T P . .
H2 H 0.1250 0.1250 0.3665 0.056 Uiso 1 2 calc RS T P . .
C4 C 0.0024(7) 0.2166(3) 0.48841(8) 0.0342(13) Uani 1 1 d . . . . .
H4 H -0.0776 0.2776 0.4883 0.041 Uiso 1 1 calc R . . . .
C5 C 0.0614(9) 0.1706(4) 0.52309(9) 0.0347(13) Uani 1 1 d . . . . .
C9 C 0.0649(9) 0.1700(4) 0.45354(8) 0.0330(13) Uani 1 1 d . . . . .
C10 C -0.0155(7) 0.2174(4) 0.56091(10) 0.0482(15) Uani 1 1 d . . . . .
H10A H -0.0882 0.1623 0.5745 0.072 Uiso 1 1 calc GR . . . .
H10B H -0.0973 0.2787 0.5553 0.072 Uiso 1 1 calc GR . . . .
H10C H 0.0901 0.2407 0.5770 0.072 Uiso 1 1 calc GR . . . .


_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 0.8501 . ?
N3 H3 0.8600 . ?
N3 C2 1.329(4) . ?
N3 C9 1.389(4) . ?
C2 N3 1.329(4) 2 ?
C2 H2 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.374(5) . ?
C4 C9 1.390(5) . ?
C5 C5 1.422(9) 2 ?
C5 C10 1.511(5) . ?
C9 C9 1.381(9) 2 ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 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
C2 N3 H3 127.4 . . ?
C2 N3 C9 105.1(4) . . ?
C9 N3 H3 127.4 . . ?
N3 C2 N3 114.1(4) 2 . ?
N3 C2 H2 123.0 . . ?
N3 C2 H2 123.0 2 . ?
C5 C4 H4 120.7 . . ?
C5 C4 C9 118.6(4) . . ?
C9 C4 H4 120.7 . . ?
C4 C5 C5 120.4(3) . 2 ?
C4 C5 C10 118.5(4) . . ?
C5 C5 C10 121.1(2) 2 . ?
N3 C9 C4 131.2(4) . . ?
C9 C9 N3 107.8(2) 2 . ?
C9 C9 C4 121.0(2) 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 . . ?

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
C2 N3 C9 C4 -179.3(6) . . . . ?
C2 N3 C9 C9 2.4(8) . . . 2 ?
C5 C4 C9 N3 -178.7(6) . . . . ?
C5 C4 C9 C9 -0.6(12) . . . 2 ?
C9 N3 C2 N3 -0.9(3) . . . 2 ?
C9 C4 C5 C5 2.0(11) . . . 2 ?
C9 C4 C5 C10 -176.6(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
