# 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_kapoor-d171
_database_code_depnum_ccdc_archive 'CCDC 1538920'
_audit_update_record             
;
2018-01-18 deposited with the CCDC.
2018-01-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
(4-Chlorophenyl)(3-phenylimidazo[1,2-a]pyridin-2-yl)methanone 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H13 Cl N2 O'
_chemical_formula_sum            'C20 H13 Cl N2 O'
_chemical_formula_weight         332.77

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_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                   6.3278(5)
_cell_length_b                   13.3923(10)
_cell_length_c                   18.8088(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1593.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1328
_cell_measurement_theta_min      3.8700
_cell_measurement_theta_max      26.8310

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            WHITE
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.248
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_T_max  0.952
_exptl_absorpt_process_details   'Crys Alis Red'

_exptl_special_details           
;
 CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'Omega scan'
_diffrn_detector_area_resol_mean 16.1049
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            4421
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0588
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.59
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3071
_reflns_number_gt                2301
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Oxford Diffraction,2010)'
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction,2010)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction,2010)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997)'
_computing_publication_material  PLATON(Spek,2009)

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0277P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0084(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(8)
_refine_ls_number_reflns         3071
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.0841
_refine_ls_wR_factor_gt          0.0744
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_restrained_S_all      0.992
_refine_ls_shift/su_max          0.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.03362(13) 0.80409(6) 0.96587(4) 0.0746(3) Uani 1 1 d . . .
O1 O 0.5086(3) 0.85338(13) 0.65433(8) 0.0554(5) Uani 1 1 d . . .
C11 C 0.4393(4) 0.87667(16) 0.77538(12) 0.0342(5) Uani 1 1 d . . .
N9 N 1.0484(3) 1.03092(14) 0.67361(10) 0.0358(5) Uani 1 1 d . . .
C8 C 1.0062(4) 1.05381(17) 0.74494(12) 0.0367(6) Uani 1 1 d . . .
C3 C 0.8873(4) 0.96954(17) 0.64982(12) 0.0346(6) Uani 1 1 d . . .
C17 C 0.8820(4) 0.93330(17) 0.57560(12) 0.0372(6) Uani 1 1 d . . .
C10 C 0.5648(4) 0.89478(17) 0.70940(12) 0.0383(6) Uani 1 1 d . . .
N1 N 0.8288(3) 1.01014(14) 0.76628(10) 0.0398(5) Uani 1 1 d . . .
C16 C 0.2451(4) 0.82896(18) 0.76818(13) 0.0433(6) Uani 1 1 d . . .
H16 H 0.1978 0.8117 0.7230 0.052 Uiso 1 1 calc R . .
C12 C 0.5048(5) 0.90102(18) 0.84373(12) 0.0493(7) Uani 1 1 d . . .
H12 H 0.6341 0.9327 0.8502 0.059 Uiso 1 1 calc R . .
C2 C 0.7560(4) 0.95769(17) 0.70826(12) 0.0357(6) Uani 1 1 d . . .
C6 C 1.3590(4) 1.12646(19) 0.67524(15) 0.0490(7) Uani 1 1 d . . .
H6 H 1.4764 1.1528 0.6522 0.059 Uiso 1 1 calc R . .
C14 C 0.1905(4) 0.83260(19) 0.89281(14) 0.0450(7) Uani 1 1 d . . .
C5 C 1.3265(4) 1.14610(18) 0.74854(14) 0.0489(7) Uani 1 1 d . . .
H5 H 1.4259 1.1832 0.7736 0.059 Uiso 1 1 calc R . .
C15 C 0.1215(4) 0.80672(19) 0.82617(14) 0.0485(7) Uani 1 1 d . . .
H15 H -0.0075 0.7745 0.8203 0.058 Uiso 1 1 calc R . .
C7 C 1.2211(4) 1.07001(19) 0.63910(14) 0.0447(7) Uani 1 1 d . . .
H7 H 1.2421 1.0574 0.5910 0.054 Uiso 1 1 calc R . .
C22 C 0.7223(4) 0.9630(2) 0.53043(13) 0.0482(7) Uani 1 1 d . . .
H22 H 0.6181 1.0060 0.5471 0.058 Uiso 1 1 calc R . .
C18 C 1.0373(5) 0.8703(2) 0.54955(12) 0.0541(7) Uani 1 1 d . . .
H18 H 1.1484 0.8508 0.5788 0.065 Uiso 1 1 calc R . .
C13 C 0.3813(4) 0.8790(2) 0.90203(15) 0.0565(8) Uani 1 1 d . . .
H13 H 0.4275 0.8955 0.9475 0.068 Uiso 1 1 calc R . .
C4 C 1.1530(4) 1.11171(18) 0.78234(14) 0.0473(7) Uani 1 1 d . . .
H4 H 1.1312 1.1264 0.8301 0.057 Uiso 1 1 calc R . .
C20 C 0.8671(5) 0.8666(2) 0.43618(14) 0.0619(9) Uani 1 1 d . . .
H20 H 0.8616 0.8441 0.3894 0.074 Uiso 1 1 calc R . .
C21 C 0.7143(5) 0.9302(2) 0.46124(14) 0.0574(8) Uani 1 1 d . . .
H21 H 0.6056 0.9511 0.4315 0.069 Uiso 1 1 calc R . .
C19 C 1.0273(6) 0.8362(2) 0.47986(14) 0.0659(9) Uani 1 1 d . . .
H19 H 1.1299 0.7925 0.4629 0.079 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
Cl1 C14 1.738(3) . ?
O1 C10 1.227(3) . ?
C11 C12 1.390(3) . ?
C11 C16 1.392(3) . ?
C11 C10 1.493(3) . ?
N9 C7 1.375(3) . ?
N9 C3 1.384(3) . ?
N9 C8 1.402(3) . ?
C8 N1 1.328(3) . ?
C8 C4 1.400(3) . ?
C3 C2 1.387(3) . ?
C3 C17 1.478(3) . ?
C17 C22 1.379(3) . ?
C17 C18 1.385(3) . ?
C10 C2 1.475(3) . ?
N1 C2 1.377(3) . ?
C16 C15 1.375(3) . ?
C16 H16 0.9300 . ?
C12 C13 1.378(3) . ?
C12 H12 0.9300 . ?
C6 C7 1.340(3) . ?
C6 C5 1.419(4) . ?
C6 H6 0.9300 . ?
C14 C13 1.369(3) . ?
C14 C15 1.372(3) . ?
C5 C4 1.349(4) . ?
C5 H5 0.9300 . ?
C15 H15 0.9300 . ?
C7 H7 0.9300 . ?
C22 C21 1.375(3) . ?
C22 H22 0.9300 . ?
C18 C19 1.390(3) . ?
C18 H18 0.9300 . ?
C13 H13 0.9300 . ?
C4 H4 0.9300 . ?
C20 C19 1.367(4) . ?
C20 C21 1.372(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C19 H19 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
C12 C11 C16 117.5(2) . . ?
C12 C11 C10 124.9(2) . . ?
C16 C11 C10 117.6(2) . . ?
C7 N9 C3 131.2(2) . . ?
C7 N9 C8 121.3(2) . . ?
C3 N9 C8 107.4(2) . . ?
N1 C8 C4 130.8(2) . . ?
N1 C8 N9 110.7(2) . . ?
C4 C8 N9 118.4(2) . . ?
N9 C3 C2 104.65(19) . . ?
N9 C3 C17 121.1(2) . . ?
C2 C3 C17 134.2(2) . . ?
C22 C17 C18 118.5(2) . . ?
C22 C17 C3 120.3(2) . . ?
C18 C17 C3 121.2(2) . . ?
O1 C10 C2 118.9(2) . . ?
O1 C10 C11 118.3(2) . . ?
C2 C10 C11 122.8(2) . . ?
C8 N1 C2 105.54(18) . . ?
C15 C16 C11 121.7(2) . . ?
C15 C16 H16 119.2 . . ?
C11 C16 H16 119.2 . . ?
C13 C12 C11 121.1(2) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
N1 C2 C3 111.7(2) . . ?
N1 C2 C10 123.7(2) . . ?
C3 C2 C10 124.6(2) . . ?
C7 C6 C5 120.2(3) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C13 C14 C15 120.7(3) . . ?
C13 C14 Cl1 120.2(2) . . ?
C15 C14 Cl1 119.0(2) . . ?
C4 C5 C6 120.8(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C14 C15 C16 119.3(2) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C6 C7 N9 119.5(2) . . ?
C6 C7 H7 120.2 . . ?
N9 C7 H7 120.2 . . ?
C21 C22 C17 121.2(3) . . ?
C21 C22 H22 119.4 . . ?
C17 C22 H22 119.4 . . ?
C17 C18 C19 120.1(3) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C14 C13 C12 119.8(3) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C5 C4 C8 119.5(2) . . ?
C5 C4 H4 120.3 . . ?
C8 C4 H4 120.3 . . ?
C19 C20 C21 120.1(3) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C22 119.8(3) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C20 C19 C18 120.2(3) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?

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
C7 N9 C8 N1 178.2(2) . . . . ?
C3 N9 C8 N1 0.0(3) . . . . ?
C7 N9 C8 C4 -4.8(3) . . . . ?
C3 N9 C8 C4 177.0(2) . . . . ?
C7 N9 C3 C2 -178.4(2) . . . . ?
C8 N9 C3 C2 -0.4(2) . . . . ?
C7 N9 C3 C17 0.8(4) . . . . ?
C8 N9 C3 C17 178.7(2) . . . . ?
N9 C3 C17 C22 -114.6(3) . . . . ?
C2 C3 C17 C22 64.3(4) . . . . ?
N9 C3 C17 C18 64.6(3) . . . . ?
C2 C3 C17 C18 -116.6(3) . . . . ?
C12 C11 C10 O1 166.4(2) . . . . ?
C16 C11 C10 O1 -11.4(3) . . . . ?
C12 C11 C10 C2 -11.8(4) . . . . ?
C16 C11 C10 C2 170.4(2) . . . . ?
C4 C8 N1 C2 -176.1(3) . . . . ?
N9 C8 N1 C2 0.5(3) . . . . ?
C12 C11 C16 C15 0.2(4) . . . . ?
C10 C11 C16 C15 178.2(2) . . . . ?
C16 C11 C12 C13 -0.2(4) . . . . ?
C10 C11 C12 C13 -178.1(2) . . . . ?
C8 N1 C2 C3 -0.8(3) . . . . ?
C8 N1 C2 C10 177.7(2) . . . . ?
N9 C3 C2 N1 0.7(3) . . . . ?
C17 C3 C2 N1 -178.2(2) . . . . ?
N9 C3 C2 C10 -177.7(2) . . . . ?
C17 C3 C2 C10 3.3(4) . . . . ?
O1 C10 C2 N1 177.7(2) . . . . ?
C11 C10 C2 N1 -4.1(3) . . . . ?
O1 C10 C2 C3 -4.0(4) . . . . ?
C11 C10 C2 C3 174.1(2) . . . . ?
C7 C6 C5 C4 -2.5(4) . . . . ?
C13 C14 C15 C16 -0.8(4) . . . . ?
Cl1 C14 C15 C16 -179.90(19) . . . . ?
C11 C16 C15 C14 0.3(4) . . . . ?
C5 C6 C7 N9 -0.3(4) . . . . ?
C3 N9 C7 C6 -178.4(2) . . . . ?
C8 N9 C7 C6 3.9(4) . . . . ?
C18 C17 C22 C21 0.8(4) . . . . ?
C3 C17 C22 C21 -180.0(2) . . . . ?
C22 C17 C18 C19 -1.7(4) . . . . ?
C3 C17 C18 C19 179.1(2) . . . . ?
C15 C14 C13 C12 0.7(4) . . . . ?
Cl1 C14 C13 C12 179.8(2) . . . . ?
C11 C12 C13 C14 -0.2(4) . . . . ?
C6 C5 C4 C8 1.6(4) . . . . ?
N1 C8 C4 C5 178.3(2) . . . . ?
N9 C8 C4 C5 1.9(4) . . . . ?
C19 C20 C21 C22 -0.2(4) . . . . ?
C17 C22 C21 C20 0.1(4) . . . . ?
C21 C20 C19 C18 -0.6(4) . . . . ?
C17 C18 C19 C20 1.6(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.033
