# 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_5965
_database_code_depnum_ccdc_archive 'CCDC 1018375'
_audit_update_record             
;
2014-08-07 deposited with the CCDC.
2015-02-25 downloaded from the CCDC.
;

_audit_creation_date             2014-07-16T14:39:06-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
6-nitro-2,3-diphenylimidazo[1,2-a]pyridine 1-oxide
;
_chemical_name_common            ' '
_chemical_formula_moiety         'C19 H17 Br N2 O3'
_chemical_formula_analytical     ' '
_chemical_formula_sum            'C19 H17 Br N2 O3'
_chemical_formula_weight         401.25

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.6130(4)
_cell_length_b                   16.0480(14)
_cell_length_c                   18.9931(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1710.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5561
_cell_measurement_theta_min      2.465
_cell_measurement_theta_max      23.802

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.401
_exptl_crystal_size_mid          0.043
_exptl_crystal_size_min          0.023
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_F_000             816

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.424
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
        (compiled Jan 14 2014,18:38:05)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.80289
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.443
_shelx_estimated_absorpt_T_max   0.946

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_reflns_av_R_equivalents  0.1113
_diffrn_reflns_number            54577
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.492
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_number_total             3355
_reflns_number_gt                2765
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0368P)²+0.0146P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3355
_refine_ls_number_parameters     242
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0753
_refine_ls_wR_factor_gt          0.0688
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.033
_refine_ls_shift/su_mean         0.002
_refine_ls_abs_structure_details 
;
 Flack x determined using 1026 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.026(6)
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.066

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br 0.03224(8) 1.04156(3) 0.67445(3) 0.03390(16) Uani 1 d . .
O1 O 0.9155(6) 0.7405(2) 0.66435(17) 0.0337(8) Uani 1 d . .
O2 O 1.0153(8) 0.7653(3) 0.5239(2) 0.0456(10) Uani 1 d . .
H1O H 1.172(7) 0.745(5) 0.514(4) 0.10(3) Uiso 1 d . .
H2O H 0.989(14) 0.753(5) 0.5721(17) 0.11(3) Uiso 1 d . .
O3 O 0.5984(8) 0.6143(3) 0.6554(2) 0.0487(11) Uani 1 d . .
H3O H 0.716(11) 0.658(4) 0.654(4) 0.10(3) Uiso 1 d . .
H4O H 0.507(12) 0.619(5) 0.613(2) 0.10(3) Uiso 1 d . .
N1 N 0.8282(7) 0.8015(3) 0.7048(2) 0.0261(10) Uani 1 d . .
N2 N 0.6009(7) 0.9032(3) 0.7417(2) 0.0239(10) Uani 1 d . .
C1 C 0.6468(8) 0.8508(3) 0.6861(3) 0.0248(11) Uani 1 d . .
C2 C 0.5054(9) 0.8524(3) 0.6255(2) 0.0276(11) Uani 1 d . .
H2 H 0.5375 0.8159 0.5873 0.033 Uiso 1 calc . .
C3 C 0.3207(9) 0.9075(3) 0.6222(3) 0.0304(12) Uani 1 d . .
H3 H 0.2179 0.9085 0.5825 0.037 Uiso 1 calc . .
C4 C 0.2846(7) 0.9636(3) 0.6794(2) 0.0275(10) Uani 1 d . .
C5 C 0.4233(8) 0.9625(3) 0.7376(2) 0.0263(10) Uani 1 d . .
H5 H 0.3994 1.0015 0.7745 0.032 Uiso 1 calc . .
C6 C 0.7578(8) 0.8855(3) 0.7960(3) 0.0252(11) Uani 1 d . .
C7 C 0.7452(8) 0.9324(3) 0.8632(2) 0.0246(11) Uani 1 d . .
C8 C 0.5538(9) 0.9187(3) 0.9082(2) 0.0296(11) Uani 1 d . .
H8 H 0.4328 0.88 0.8957 0.036 Uiso 1 calc . .
C9 C 0.5399(8) 0.9617(3) 0.9718(2) 0.0336(11) Uani 1 d . .
H9 H 0.4106 0.9517 1.0029 0.04 Uiso 1 calc . .
C10 C 0.7127(10) 1.0186(4) 0.9897(3) 0.0389(14) Uani 1 d . .
H10 H 0.7027 1.0478 1.0331 0.047 Uiso 1 calc . .
C11 C 0.9005(9) 1.0334(4) 0.9445(3) 0.0400(13) Uani 1 d . .
H11 H 1.0192 1.073 0.9568 0.048 Uiso 1 calc . .
C12 C 0.9165(9) 0.9901(3) 0.8806(3) 0.0337(13) Uani 1 d . .
H12 H 1.0453 1.0006 0.8494 0.04 Uiso 1 calc . .
C13 C 0.8979(8) 0.8210(3) 0.7735(2) 0.0251(11) Uani 1 d . .
C14 C 1.0777(8) 0.7730(3) 0.8129(3) 0.0254(11) Uani 1 d . .
C15 C 1.0537(9) 0.7653(3) 0.8863(2) 0.0297(11) Uani 1 d . .
H15 H 0.9238 0.7911 0.9098 0.036 Uiso 1 calc . .
C16 C 1.2201(9) 0.7201(3) 0.9243(3) 0.0332(13) Uani 1 d . .
H16 H 1.203 0.7151 0.9739 0.04 Uiso 1 calc . .
C17 C 1.4100(9) 0.6821(3) 0.8914(3) 0.0370(13) Uani 1 d . .
H17 H 1.5236 0.6516 0.918 0.044 Uiso 1 calc . .
C18 C 1.4335(8) 0.6891(3) 0.8185(3) 0.0342(12) Uani 1 d . .
H18 H 1.5645 0.6635 0.7954 0.041 Uiso 1 calc . .
C19 C 1.2679(9) 0.7332(3) 0.7797(3) 0.0326(13) Uani 1 d . .
H19 H 1.2836 0.7363 0.73 0.039 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
Br C4 1.892(5) . ?
O1 N1 1.338(5) . ?
N1 C1 1.336(6) . ?
N1 C13 1.398(6) . ?
N2 C1 1.375(6) . ?
N2 C5 1.381(6) . ?
N2 C6 1.385(6) . ?
C1 C2 1.399(7) . ?
C2 C3 1.364(7) . ?
C3 C4 1.425(7) . ?
C4 C5 1.351(6) . ?
C6 C13 1.369(7) . ?
C6 C7 1.483(7) . ?
C7 C12 1.376(7) . ?
C7 C8 1.391(7) . ?
C8 C9 1.392(6) . ?
C9 C10 1.375(7) . ?
C10 C11 1.380(7) . ?
C11 C12 1.402(7) . ?
C13 C14 1.473(6) . ?
C14 C19 1.394(7) . ?
C14 C15 1.407(7) . ?
C15 C16 1.385(7) . ?
C16 C17 1.377(7) . ?
C17 C18 1.395(7) . ?
C18 C19 1.381(7) . ?

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
C1 N1 O1 124.0(4) . . ?
C1 N1 C13 109.2(4) . . ?
O1 N1 C13 126.6(4) . . ?
C1 N2 C5 120.9(4) . . ?
C1 N2 C6 109.1(4) . . ?
C5 N2 C6 130.0(4) . . ?
N1 C1 N2 107.5(4) . . ?
N1 C1 C2 131.5(4) . . ?
N2 C1 C2 121.0(4) . . ?
C3 C2 C1 118.7(4) . . ?
C2 C3 C4 118.9(5) . . ?
C5 C4 C3 122.2(4) . . ?
C5 C4 Br 118.7(4) . . ?
C3 C4 Br 119.1(3) . . ?
C4 C5 N2 118.1(4) . . ?
C13 C6 N2 106.7(4) . . ?
C13 C6 C7 132.8(4) . . ?
N2 C6 C7 120.4(4) . . ?
C12 C7 C8 119.9(5) . . ?
C12 C7 C6 121.0(4) . . ?
C8 C7 C6 119.1(4) . . ?
C7 C8 C9 119.9(5) . . ?
C10 C9 C8 120.3(5) . . ?
C9 C10 C11 120.0(5) . . ?
C10 C11 C12 120.2(5) . . ?
C7 C12 C11 119.8(5) . . ?
C6 C13 N1 107.4(4) . . ?
C6 C13 C14 129.1(4) . . ?
N1 C13 C14 123.3(4) . . ?
C19 C14 C15 118.8(5) . . ?
C19 C14 C13 122.3(4) . . ?
C15 C14 C13 118.9(4) . . ?
C16 C15 C14 119.8(5) . . ?
C17 C16 C15 121.2(5) . . ?
C16 C17 C18 119.2(5) . . ?
C19 C18 C17 120.5(5) . . ?
C18 C19 C14 120.6(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
O1 N1 C1 N2 177.4(4) . . . . ?
C13 N1 C1 N2 1.1(5) . . . . ?
O1 N1 C1 C2 1.0(8) . . . . ?
C13 N1 C1 C2 -175.3(5) . . . . ?
C5 N2 C1 N1 179.1(4) . . . . ?
C6 N2 C1 N1 -0.2(5) . . . . ?
C5 N2 C1 C2 -4.1(7) . . . . ?
C6 N2 C1 C2 176.7(4) . . . . ?
N1 C1 C2 C3 176.3(5) . . . . ?
N2 C1 C2 C3 0.3(7) . . . . ?
C1 C2 C3 C4 2.5(7) . . . . ?
C2 C3 C4 C5 -1.8(7) . . . . ?
C2 C3 C4 Br 178.8(4) . . . . ?
C3 C4 C5 N2 -1.9(7) . . . . ?
Br C4 C5 N2 177.5(3) . . . . ?
C1 N2 C5 C4 4.8(6) . . . . ?
C6 N2 C5 C4 -176.2(5) . . . . ?
C1 N2 C6 C13 -0.9(5) . . . . ?
C5 N2 C6 C13 180.0(4) . . . . ?
C1 N2 C6 C7 -179.1(4) . . . . ?
C5 N2 C6 C7 1.8(7) . . . . ?
C13 C6 C7 C12 74.6(7) . . . . ?
N2 C6 C7 C12 -107.7(6) . . . . ?
C13 C6 C7 C8 -106.8(6) . . . . ?
N2 C6 C7 C8 70.9(6) . . . . ?
C12 C7 C8 C9 -1.9(7) . . . . ?
C6 C7 C8 C9 179.6(4) . . . . ?
C7 C8 C9 C10 1.0(7) . . . . ?
C8 C9 C10 C11 0.1(8) . . . . ?
C9 C10 C11 C12 -0.4(8) . . . . ?
C8 C7 C12 C11 1.6(8) . . . . ?
C6 C7 C12 C11 -179.9(5) . . . . ?
C10 C11 C12 C7 -0.4(8) . . . . ?
N2 C6 C13 N1 1.5(5) . . . . ?
C7 C6 C13 N1 179.4(5) . . . . ?
N2 C6 C13 C14 -173.6(5) . . . . ?
C7 C6 C13 C14 4.3(9) . . . . ?
C1 N1 C13 C6 -1.7(5) . . . . ?
O1 N1 C13 C6 -177.9(4) . . . . ?
C1 N1 C13 C14 173.8(4) . . . . ?
O1 N1 C13 C14 -2.3(7) . . . . ?
C6 C13 C14 C19 -154.2(5) . . . . ?
N1 C13 C14 C19 31.3(7) . . . . ?
C6 C13 C14 C15 27.4(7) . . . . ?
N1 C13 C14 C15 -147.1(5) . . . . ?
C19 C14 C15 C16 1.2(7) . . . . ?
C13 C14 C15 C16 179.7(4) . . . . ?
C14 C15 C16 C17 0.0(7) . . . . ?
C15 C16 C17 C18 -0.4(8) . . . . ?
C16 C17 C18 C19 -0.4(8) . . . . ?
C17 C18 C19 C14 1.6(8) . . . . ?
C15 C14 C19 C18 -1.9(7) . . . . ?
C13 C14 C19 C18 179.6(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 O2 0.95 2.48 3.409(6) 164.4 3_466
C5 H5 O3 0.95 2.25 3.176(6) 165.4 4_656
O3 H3O O1 0.97(3) 1.74(3) 2.701(5) 172(7) .
O3 H3O N1 0.97(3) 2.57(5) 3.402(6) 145(6) .
O2 H2O O1 0.95(3) 1.81(3) 2.754(5) 173(7) .

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: water'
