# Electronic Supplementary Material (ESI) for ChemComm.
# 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. 
# 
#######################################################################

data_AC_YJ_040215_0m
_database_code_depnum_ccdc_archive 'CCDC 1430826'
_audit_update_record             
;
2015-10-12 deposited with the CCDC.
2015-12-17 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_EXPT005_AC_YJ_040215_0m     
;
PROBLEM: _exptl_crystal_description is missing
RESPONSE: Platy
;
_vrf_DIFF003_AC_YJ_040215_0m     
;
PROBLEM: _diffrn_measurement_device_type is missing
RESPONSE: Brukner Smart APEXii CCD Diffractometer
;
_vrf_CRYSS02_AC_YJ_040215_0m     
;
PROBLEM: The value of _exptl_crystal_size_min is > 0.6
RESPONSE: 7.253
;

# Added during the CSD deposition process: Monday 12th of October 2015 03:46:01 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2013
_chemical_name_systematic        1-phenylimidazo[1,5-a]pyridine
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H10 N2'
_chemical_formula_weight         194.23

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.2543(11)
_cell_length_b                   10.8861(17)
_cell_length_c                   12.636(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     997.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Platy
_exptl_crystal_colour            White
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_F_000             408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          1.254
_exptl_crystal_size_mid          1.079
_exptl_crystal_size_min          0.993
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.908
_shelx_estimated_absorpt_T_max   0.926
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13412
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.469
_diffrn_reflns_theta_max         33.290
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3620
_reflns_number_gt                3154
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.711
_reflns_Friedel_fraction_max     0.912
_reflns_Friedel_fraction_full    1.000

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1000P)²]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1234 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.1(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3620
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_ref         0.1449
_refine_ls_wR_factor_gt          0.1365
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_restrained_S_all      1.139
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.1002(3) 1.16212(18) 0.77426(18) 0.0577(5) Uani 1 1 d . . . . .
H1 H 0.0423 1.2040 0.7194 0.069 Uiso 1 1 calc R U . . .
C5 C 0.23876(19) 0.97647(13) 0.84226(10) 0.0365(3) Uani 1 1 d . . . . .
C4 C 0.2725(2) 1.03795(14) 0.93707(11) 0.0428(3) Uani 1 1 d . . . . .
H4 H 0.3310 0.9969 0.9922 0.051 Uiso 1 1 calc R U . . .
C6 C 0.1529(2) 1.04031(16) 0.76063(13) 0.0480(4) Uani 1 1 d . . . . .
H6 H 0.1306 1.0012 0.6964 0.058 Uiso 1 1 calc R U . . .
C3 C 0.2199(3) 1.15963(16) 0.95050(14) 0.0537(4) Uani 1 1 d . . . . .
H3 H 0.2429 1.1997 1.0142 0.064 Uiso 1 1 calc R U . . .
C2 C 0.1334(3) 1.22077(16) 0.86873(18) 0.0589(5) Uani 1 1 d . . . . .
H2 H 0.0974 1.3021 0.8776 0.071 Uiso 1 1 calc R U . . .
C9 C 0.28771(18) 0.75205(12) 0.90000(11) 0.0351(3) Uani 1 1 d . . . . .
C10 C 0.2336(2) 0.73566(14) 1.00676(12) 0.0424(3) Uani 1 1 d . . . . .
H10 H 0.1876 0.8015 1.0455 0.051 Uiso 1 1 calc R U . . .
C11 C 0.2493(3) 0.62312(16) 1.05221(15) 0.0537(4) Uani 1 1 d . . . . .
H11 H 0.2139 0.6120 1.1223 0.064 Uiso 1 1 calc R U . . .
C7 C 0.29253(19) 0.84783(13) 0.82745(10) 0.0367(3) Uani 1 1 d . . . . .
C13 C 0.3702(2) 0.53564(15) 0.89152(17) 0.0529(4) Uani 1 1 d . . . . .
H13 H 0.4159 0.4693 0.8533 0.064 Uiso 1 1 calc R U . . .
C8 C 0.3927(3) 0.68823(17) 0.74473(14) 0.0525(4) Uani 1 1 d . . . . .
H8 H 0.4394 0.6376 0.6919 0.063 Uiso 1 1 calc R U . . .
C12 C 0.3198(3) 0.52202(16) 0.99308(18) 0.0569(5) Uani 1 1 d . . . . .
H12 H 0.3310 0.4456 1.0253 0.068 Uiso 1 1 calc R U . . .
N1 N 0.35318(18) 0.64994(11) 0.84455(11) 0.0419(3) Uani 1 1 d . . . . .
N2 N 0.3567(2) 0.80588(15) 0.73203(10) 0.0497(3) Uani 1 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 C2 1.375(3) . ?
C1 C6 1.391(3) . ?
C5 C6 1.391(2) . ?
C5 C4 1.3939(19) . ?
C5 C7 1.466(2) . ?
C4 C3 1.389(2) . ?
C3 C2 1.380(3) . ?
C9 C7 1.3888(19) . ?
C9 N1 1.3972(17) . ?
C9 C10 1.416(2) . ?
C10 C11 1.358(2) . ?
C11 C12 1.425(3) . ?
C7 N2 1.3707(18) . ?
C13 C12 1.343(3) . ?
C13 N1 1.384(2) . ?
C8 N2 1.317(2) . ?
C8 N1 1.359(2) . ?

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 C6 120.12(17) . . ?
C6 C5 C4 118.42(14) . . ?
C6 C5 C7 120.12(14) . . ?
C4 C5 C7 121.45(13) . . ?
C3 C4 C5 120.99(14) . . ?
C1 C6 C5 120.51(17) . . ?
C2 C3 C4 119.56(17) . . ?
C1 C2 C3 120.39(16) . . ?
C7 C9 N1 104.93(12) . . ?
C7 C9 C10 136.92(13) . . ?
N1 C9 C10 118.14(13) . . ?
C11 C10 C9 119.56(15) . . ?
C10 C11 C12 120.34(17) . . ?
N2 C7 C9 109.83(13) . . ?
N2 C7 C5 121.39(13) . . ?
C9 C7 C5 128.78(12) . . ?
C12 C13 N1 119.00(15) . . ?
N2 C8 N1 111.68(14) . . ?
C13 C12 C11 120.90(16) . . ?
C8 N1 C13 130.91(14) . . ?
C8 N1 C9 107.05(13) . . ?
C13 N1 C9 122.04(14) . . ?
C8 N2 C7 106.51(14) . . ?

_refine_diff_density_max         0.402
_refine_diff_density_min         -0.695
_refine_diff_density_rms         0.198

_shelxl_version_number           2013-2



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
