# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_20170457
_database_code_depnum_ccdc_archive 'CCDC 1838820'
_audit_update_record             
;
2018-04-23 deposited with the CCDC.
2018-07-17 downloaded from the CCDC.
;
_audit_creation_date             2017-04-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        1,3-diphenylimidazo[1,5-a]pyridine
_chemical_formula_moiety         'C19 H14 N2'
_chemical_formula_sum            'C19 H14 N2'
_chemical_formula_weight         270.32
_chemical_absolute_configuration ?
_chemical_melting_point          383-384
_chemical_oxdiff_formula         C38H70N2O2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 '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           36
_space_group_name_H-M_alt        'C m c 21'
_space_group_name_Hall           'C 2c -2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y, z+1/2'
'-x, y, z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z'

_cell_length_a                   23.8510(10)
_cell_length_b                   7.4217(4)
_cell_length_c                   7.8859(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1395.92(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1174
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.5100
_cell_measurement_theta_min      5.6510
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.591
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            2575
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.024
_diffrn_reflns_theta_max         67.024
_diffrn_reflns_theta_min         3.706
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -103.00   -5.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000    0.0000 98

#__ type_ start__ end____ width___ exp.time_
  2 omega  -33.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000 -180.0000 98

#__ type_ start__ end____ width___ exp.time_
  3 omega   57.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -150.0000 53

#__ type_ start__ end____ width___ exp.time_
  4 omega  -34.00   59.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000 -120.0000 93

#__ type_ start__ end____ width___ exp.time_
  5 omega   57.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -60.0000 53

#__ type_ start__ end____ width___ exp.time_
  6 omega   57.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  120.0000 53

#__ type_ start__ end____ width___ exp.time_
  7 omega   37.00   91.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 54

#__ type_ start__ end____ width___ exp.time_
  8 omega   38.00  109.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 71

#__ type_ start__ end____ width___ exp.time_
  9 omega   82.00  178.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -60.0000 96

#__ type_ start__ end____ width___ exp.time_
 10 omega   91.00  176.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -150.0000 85

#__ type_ start__ end____ width___ exp.time_
 11 omega   39.00   65.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 12 omega  106.00  169.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   30.0000 63

#__ type_ start__ end____ width___ exp.time_
 13 omega   59.00   88.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 29

#__ type_ start__ end____ width___ exp.time_
 14 omega  112.00  170.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -120.0000 58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0571581000
_diffrn_orient_matrix_UB_12      0.0864225000
_diffrn_orient_matrix_UB_13      0.0408322000
_diffrn_orient_matrix_UB_21      -0.0194733000
_diffrn_orient_matrix_UB_22      -0.1771708000
_diffrn_orient_matrix_UB_23      0.0832066000
_diffrn_orient_matrix_UB_31      0.0230489500
_diffrn_orient_matrix_UB_32      0.0652386500
_diffrn_orient_matrix_UB_33      0.1717654000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.844
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                965
_reflns_number_total             1020
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.100
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -1.6(13)
_refine_ls_extinction_coef       0.0017(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     98
_refine_ls_number_reflns         1020
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0316
_refine_ls_restrained_S_all      1.057
_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)+(0.0485P)²+0.1257P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0864
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 2.6(13)
 -1.6(13)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Shared sites
{N2, C10}
4. Uiso/Uaniso restraints and constraints
Uiso(N2) = Uiso(C10)
5. Others
 Fixed Sof: C10(0.5) N2(0.5)
6.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C9(H9)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
C1 C 0.61620(9) 0.1401(3) 0.2032(4) 0.0513(6) Uani 1 1 d . . . . .
H1 H 0.5891 0.0638 0.1580 0.062 Uiso 1 1 calc R . . . .
C2 C 0.66918(10) 0.1445(4) 0.1319(4) 0.0647(7) Uani 1 1 d . . . . .
H2 H 0.6775 0.0710 0.0397 0.078 Uiso 1 1 calc R . . . .
C3 C 0.70984(10) 0.2581(4) 0.1974(5) 0.0685(9) Uani 1 1 d . . . . .
H3 H 0.7455 0.2614 0.1497 0.082 Uiso 1 1 calc R . . . .
C4 C 0.69697(9) 0.3657(4) 0.3334(4) 0.0634(8) Uani 1 1 d . . . . .
H4 H 0.7243 0.4418 0.3778 0.076 Uiso 1 1 calc R . . . .
C5 C 0.64397(9) 0.3631(4) 0.4060(4) 0.0537(6) Uani 1 1 d . . . . .
H5 H 0.6358 0.4376 0.4976 0.064 Uiso 1 1 calc R . . . .
C6 C 0.60284(8) 0.2480(3) 0.3410(4) 0.0443(6) Uani 1 1 d . . . . .
C7 C 0.54532(9) 0.2471(3) 0.4087(3) 0.0423(5) Uani 1 1 d . . . . .
C8 C 0.55838(10) 0.2930(3) 0.7287(4) 0.0525(6) Uani 1 1 d . . . . .
H8 H 0.5982(10) 0.286(3) 0.721(4) 0.051(6) Uiso 1 1 d . . . . .
C9 C 0.52981(11) 0.3092(4) 0.8743(4) 0.0594(7) Uani 1 1 d . . . . .
H9 H 0.5491 0.3206 0.9761 0.071 Uiso 1 1 calc R . . . .
C10 C 0.52928(8) 0.2761(3) 0.5750(3) 0.0425(5) Uiso 0.5 1 d . . . . .
N1 N 0.5000 0.2269(4) 0.3087(4) 0.0427(6) Uani 1 2 d S T P . .
N2 N 0.52928(8) 0.2761(3) 0.5750(3) 0.0425(5) Uiso 0.5 1 d . . . . .


_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
C1 H1 0.9300 . ?
C1 C2 1.384(3) . ?
C1 C6 1.387(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.385(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.372(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.388(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.398(3) . ?
C6 C7 1.472(3) . ?
C7 C10 1.382(4) . ?
C7 N1 1.346(3) . ?
C8 H8 0.95(2) . ?
C8 C9 1.341(4) . ?
C8 C10 1.402(3) . ?
C9 C9 1.422(5) 4_655 ?
C9 H9 0.9300 . ?
C10 C10 1.397(4) 4_655 ?
C10 N2 1.397(4) 4_655 ?
N1 C7 1.346(3) 4_655 ?

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 C1 H1 119.5 . . ?
C2 C1 C6 121.0(2) . . ?
C6 C1 H1 119.5 . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.1(3) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.3(3) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.2(3) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.8(3) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 118.6(2) . . ?
C1 C6 C7 119.7(2) . . ?
C5 C6 C7 121.6(2) . . ?
C10 C7 C6 127.0(2) . . ?
N1 C7 C6 122.4(2) . . ?
N1 C7 C10 110.5(2) . . ?
C9 C8 H8 124(2) . . ?
C9 C8 C10 119.8(2) . . ?
C10 C8 H8 116(2) . . ?
C8 C9 C9 120.55(16) . 4_655 ?
C8 C9 H9 119.7 . . ?
C9 C9 H9 119.7 4_655 . ?
C7 C10 C8 134.16(19) . . ?
C7 C10 C10 106.06(12) . 4_655 ?
C7 C10 N2 106.06(12) . 4_655 ?
C10 C10 C8 119.66(14) 4_655 . ?
N2 C10 C8 119.66(14) 4_655 . ?
N2 C10 C10 0.0 4_655 4_655 ?
C7 N1 C7 106.8(3) 4_655 . ?

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
C1 C2 C3 C4 0.0(5) . . . . ?
C1 C6 C7 C10 149.6(2) . . . . ?
C1 C6 C7 N1 -34.4(3) . . . . ?
C2 C1 C6 C5 0.6(4) . . . . ?
C2 C1 C6 C7 176.9(2) . . . . ?
C2 C3 C4 C5 -0.2(5) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C4 C5 C6 C1 -0.7(4) . . . . ?
C4 C5 C6 C7 -177.0(2) . . . . ?
C5 C6 C7 C10 -34.2(4) . . . . ?
C5 C6 C7 N1 141.8(3) . . . . ?
C6 C1 C2 C3 -0.2(4) . . . . ?
C6 C7 C10 C8 -8.6(4) . . . . ?
C6 C7 C10 C10 175.49(19) . . . 4_655 ?
C6 C7 C10 N2 175.49(19) . . . 4_655 ?
C6 C7 N1 C7 -175.11(14) . . . 4_655 ?
C9 C8 C10 C7 -175.5(2) . . . . ?
C9 C8 C10 C10 -0.1(3) . . . 4_655 ?
C9 C8 C10 N2 -0.1(3) . . . 4_655 ?
C10 C7 N1 C7 1.5(3) . . . 4_655 ?
C10 C8 C9 C9 0.1(3) . . . 4_655 ?
N1 C7 C10 C8 175.0(3) . . . . ?
N1 C7 C10 C10 -0.9(2) . . . 4_655 ?
N1 C7 C10 N2 -0.9(2) . . . 4_655 ?


_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 2.6(13)
2 -1.6(13)

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
