# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_mrc210
_database_code_depnum_ccdc_archive 'CCDC 1471645'
_audit_update_record             
;
2016-03-31 deposited with the CCDC.
2016-07-22 downloaded from the CCDC.
;
_audit_creation_date             2016-01-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        
'4-Methyl-2-amino-1-(2-propynyl)pyridinium bromide'
_chemical_formula_moiety         'Br, C9 H11 N2'
_chemical_formula_sum            'C9 H11 Br N2'
_chemical_formula_weight         227.11
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C80 H80 N24 Br8'
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'
Br Br -0.2901 2.4595 '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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   16.7925(7)
_cell_length_b                   8.3062(4)
_cell_length_c                   15.0809(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.294(5)
_cell_angle_gamma                90.00
_cell_volume                     1997.21(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2328
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      28.4460
_cell_measurement_theta_min      3.1790
_exptl_absorpt_coefficient_mu    4.066
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69272
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.3168
_exptl_crystal_size_mid          0.3047
_exptl_crystal_size_min          0.2242
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_unetI/netI     0.0688
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6872
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         31.18
_diffrn_reflns_theta_min         3.17
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector_area_resol_mean 5.3095
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.878
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   15.00   62.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       12.9509   37.0000  -30.0000 47

#__ type_ start__ end____ width___ exp.time_
  2 omega  -11.00   54.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       12.9509   57.0000 -150.0000 65

#__ type_ start__ end____ width___ exp.time_
  3 omega  -46.00  -19.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.7322  -37.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
  4 omega  -73.00   -7.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.7322  -64.0000  -22.2024 66

#__ type_ start__ end____ width___ exp.time_
  5 omega  -81.00  -47.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.7322  -37.0000   90.0000 34
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0390322000
_diffrn_orient_matrix_UB_12      0.0101985000
_diffrn_orient_matrix_UB_13      0.0082116000
_diffrn_orient_matrix_UB_21      0.0045461000
_diffrn_orient_matrix_UB_22      0.0847675000
_diffrn_orient_matrix_UB_23      -0.0013834000
_diffrn_orient_matrix_UB_31      -0.0208843000
_diffrn_orient_matrix_UB_32      -0.0006563000
_diffrn_orient_matrix_UB_33      -0.0488323000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2246
_reflns_number_total             2841
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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         0.674
_refine_diff_density_min         -0.634
_refine_diff_density_rms         0.112
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         2841
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0442
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0310P)²+0.0584P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0961
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C5(H5)
2.c X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
2.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
2.e :
 C9(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
_atom_site_refinement_flags_posn
Br1 Br 0.345377(17) 0.47379(4) 0.638650(19) 0.02356(11) Uani 1 d . . .
N1 N 0.62457(13) 0.2442(3) 0.57409(15) 0.0192(5) Uani 1 d . . .
N2 N 0.53881(15) 0.3905(4) 0.63954(17) 0.0286(6) Uani 1 d . . .
H2A H 0.5816 0.4109 0.6873 0.034 Uiso 1 calc . . R
H2B H 0.4902 0.4272 0.6369 0.034 Uiso 1 calc . . R
C7 C 0.70001(17) 0.2871(4) 0.65316(19) 0.0220(6) Uani 1 d . . .
H7A H 0.6864 0.2835 0.7111 0.026 Uiso 1 calc . . R
H7B H 0.7441 0.2091 0.6574 0.026 Uiso 1 calc . . R
C1 C 0.54770(17) 0.3025(4) 0.57009(19) 0.0215(6) Uani 1 d . . .
C9 C 0.75421(19) 0.5758(5) 0.6259(2) 0.0286(7) Uani 1 d . . .
H9 H 0.7734 0.6763 0.6145 0.034 Uiso 1 calc . . R
C8 C 0.72993(17) 0.4485(4) 0.6404(2) 0.0226(7) Uani 1 d . . .
C6 C 0.63518(17) 0.1528(4) 0.50329(19) 0.0225(6) Uani 1 d . . .
H6 H 0.6885 0.1154 0.5075 0.027 Uiso 1 calc . . R
C2 C 0.47850(18) 0.2638(4) 0.4906(2) 0.0240(7) Uani 1 d . . .
H2 H 0.4253 0.3008 0.4870 0.029 Uiso 1 calc . . R
C3 C 0.48865(18) 0.1732(4) 0.41943(19) 0.0236(7) Uani 1 d . . .
C5 C 0.56959(18) 0.1156(4) 0.42709(19) 0.0243(7) Uani 1 d . . .
H5 H 0.5779 0.0523 0.3799 0.029 Uiso 1 calc . . R
C4 C 0.41540(19) 0.1378(5) 0.3338(2) 0.0326(8) Uani 1 d . . .
H4A H 0.3644 0.1397 0.3498 0.049 Uiso 1 calc . . GR
H4B H 0.4225 0.0334 0.3100 0.049 Uiso 1 calc . . GR
H4C H 0.4127 0.2178 0.2869 0.049 Uiso 1 calc . . GR

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.02175(16) 0.0279(2) 0.02232(16) 0.00295(12) 0.00877(12) 0.00581(12)
N1 0.0191(11) 0.0222(14) 0.0170(11) 0.0004(10) 0.0066(9) 0.0013(10)
N2 0.0189(12) 0.0377(19) 0.0279(13) -0.0052(12) 0.0054(10) 0.0070(12)
C7 0.0189(13) 0.0270(18) 0.0197(13) 0.0034(12) 0.0056(11) 0.0064(12)
C1 0.0239(14) 0.0217(17) 0.0210(14) 0.0030(12) 0.0101(11) 0.0022(12)
C9 0.0264(15) 0.035(2) 0.0250(15) -0.0036(14) 0.0091(12) -0.0037(14)
C8 0.0169(13) 0.030(2) 0.0199(14) -0.0033(13) 0.0047(11) 0.0036(12)
C6 0.0235(14) 0.0216(17) 0.0261(15) 0.0022(13) 0.0129(12) 0.0030(12)
C2 0.0202(13) 0.0274(19) 0.0244(15) 0.0050(13) 0.0071(11) 0.0033(13)
C3 0.0270(15) 0.0240(18) 0.0193(14) 0.0029(12) 0.0063(11) -0.0028(13)
C5 0.0300(15) 0.0255(19) 0.0200(14) -0.0007(13) 0.0116(12) 0.0010(13)
C4 0.0323(16) 0.036(2) 0.0268(15) -0.0027(15) 0.0050(13) -0.0021(15)

_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 C7 1.485(3) . ?
N1 C1 1.362(4) . ?
N1 C6 1.366(4) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N2 C1 1.324(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.466(5) . ?
C1 C2 1.420(4) . ?
C9 H9 0.9300 . ?
C9 C8 1.178(5) . ?
C6 H6 0.9300 . ?
C6 C5 1.354(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.364(4) . ?
C3 C5 1.411(4) . ?
C3 C4 1.507(4) . ?
C5 H5 0.9300 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 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
C1 N1 C7 120.5(2) . . ?
C1 N1 C6 121.1(2) . . ?
C6 N1 C7 118.2(2) . . ?
H2A N2 H2B 120.0 . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C8 C7 N1 110.8(2) . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
N1 C1 C2 118.0(3) . . ?
N2 C1 N1 120.1(2) . . ?
N2 C1 C2 121.8(3) . . ?
C8 C9 H9 180.0 . . ?
C9 C8 C7 176.7(3) . . ?
N1 C6 H6 119.4 . . ?
C5 C6 N1 121.2(3) . . ?
C5 C6 H6 119.4 . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.2(3) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 C5 118.5(3) . . ?
C2 C3 C4 120.8(3) . . ?
C5 C3 C4 120.7(3) . . ?
C6 C5 C3 119.9(3) . . ?
C6 C5 H5 120.1 . . ?
C3 C5 H5 120.1 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
15 8 1 0.1378 15.2532 8.3407 1.3100 -0.4995 0.7745 -0.3880
6 10 -9 0.1042 6.3786 10.4746 -8.9997 -0.2160 0.9294 0.2994
-16 -2 -10 0.0917 -15.7460 -2.1680 -10.1558 0.5091 -0.2413 0.8262
-9 -11 7 0.1064 -8.8172 -10.5390 7.0561 0.2946 -0.9432 -0.1535
5 -7 14 0.1535 5.0769 -7.1333 13.9776 -0.1561 -0.6009 -0.7839
12 -7 -16 0.0377 12.2863 -7.1017 -15.6394 -0.6804 -0.5245 0.5118
19 0 7 0.1383 18.8402 0.2778 6.8917 -0.6759 0.0997 -0.7302
-15 7 14 0.2127 -15.4170 6.8908 14.0385 0.7873 0.4946 -0.3681

_olex2_date_sample_data_collection 2016-01-26
_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_mrc278
_database_code_depnum_ccdc_archive 'CCDC 1471647'
_audit_update_record             
;
2016-03-31 deposited with the CCDC.
2016-07-22 downloaded from the CCDC.
;
_audit_creation_date             2015-11-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        
'5-Methyl-2-amino-1-(2-propynyl)pyridinium bromide'
_chemical_formula_moiety         'Br, C9 H11 N2'
_chemical_formula_sum            'C9 H11 Br N2'
_chemical_formula_weight         227.11
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H10 N2 Br1'
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'
Br Br -0.6763 1.2805 '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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   7.4282(7)
_cell_length_b                   14.9520(14)
_cell_length_c                   8.9188(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.547(9)
_cell_angle_gamma                90.00
_cell_volume                     987.45(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1175
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      71.0100
_cell_measurement_theta_min      5.8110
_exptl_absorpt_coefficient_mu    5.251
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82257
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.2292
_exptl_crystal_size_mid          0.0982
_exptl_crystal_size_min          0.0286
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_av_unetI/netI     0.0784
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3789
_diffrn_reflns_theta_full        68.00
_diffrn_reflns_theta_max         74.24
_diffrn_reflns_theta_min         5.79
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3095
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   23.00   50.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.7089   37.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega   68.00   95.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.7089   37.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega   39.00   97.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -45.0000  -60.0000 58

#__ type_ start__ end____ width___ exp.time_
  4 omega   67.00  172.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   15.0000 -150.0000 105

#__ type_ start__ end____ width___ exp.time_
  5 omega   62.00  125.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -64.0000   86.7494 63

#__ type_ start__ end____ width___ exp.time_
  6 omega   90.00  127.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -61.0000  120.0000 37

#__ type_ start__ end____ width___ exp.time_
  7 omega   46.00   84.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000    0.0000 38

#__ type_ start__ end____ width___ exp.time_
  8 omega   45.00  103.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -64.0000   53.5658 58

#__ type_ start__ end____ width___ exp.time_
  9 omega   43.00   70.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 10 omega   53.00   86.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000 -120.0000 33

#__ type_ start__ end____ width___ exp.time_
 11 omega  -57.00   30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   57.0000 -180.0000 87

#__ type_ start__ end____ width___ exp.time_
 12 omega  -61.00  -16.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -57.0000   30.0000 45

#__ type_ start__ end____ width___ exp.time_
 13 omega -107.00  -64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -57.0000   30.0000 43
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0207461000
_diffrn_orient_matrix_UB_12      -0.0781117000
_diffrn_orient_matrix_UB_13      -0.1099722000
_diffrn_orient_matrix_UB_21      0.1146728000
_diffrn_orient_matrix_UB_22      0.0598470000
_diffrn_orient_matrix_UB_23      -0.0959923000
_diffrn_orient_matrix_UB_31      0.1722759000
_diffrn_orient_matrix_UB_32      -0.0304392000
_diffrn_orient_matrix_UB_33      0.0935294000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1534
_reflns_number_total             1930
_reflns_odcompleteness_completeness 99.40
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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         1.320
_refine_diff_density_min         -0.872
_refine_diff_density_rms         0.171
_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     110
_refine_ls_number_reflns         1930
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0686
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1032P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1740
_refine_ls_wR_factor_ref         0.1896
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C2(H2)
2.c X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
2.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C)
2.e :
 C9(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
_atom_site_refinement_flags_posn
Br1 Br 0.08953(10) 0.31883(4) 0.01430(7) 0.0373(3) Uani 1 d . . .
N2 N 0.1402(8) 0.5131(4) 0.1909(6) 0.0356(11) Uani 1 d . . .
H2A H 0.1360 0.5623 0.1409 0.043 Uiso 1 calc . . R
H2B H 0.1155 0.4633 0.1456 0.043 Uiso 1 calc . . R
N1 N 0.2245(8) 0.5920(4) 0.4118(6) 0.0384(12) Uani 1 d . . .
C1 C 0.1850(8) 0.5139(4) 0.3382(7) 0.0324(13) Uani 1 d . . .
C3 C 0.2475(8) 0.4359(4) 0.5717(7) 0.0340(13) Uani 1 d . . .
H3 H 0.2553 0.3828 0.6261 0.041 Uiso 1 calc . . R
C8 C 0.3655(10) 0.6877(4) 0.2345(8) 0.0406(15) Uani 1 d . . .
C7 C 0.2117(10) 0.6778(4) 0.3288(8) 0.0371(14) Uani 1 d . . .
H7A H 0.0992 0.6798 0.2657 0.044 Uiso 1 calc . . R
H7B H 0.2116 0.7270 0.3997 0.044 Uiso 1 calc . . R
C6 C 0.2754(9) 0.5941(4) 0.5644(7) 0.0359(13) Uani 1 d . . .
H6 H 0.3026 0.6487 0.6107 0.043 Uiso 1 calc . . R
C4 C 0.2863(9) 0.5182(4) 0.6478(7) 0.0369(13) Uani 1 d . . .
C5 C 0.3424(10) 0.5236(5) 0.8128(8) 0.0447(16) Uani 1 d . . .
H5A H 0.2759 0.4803 0.8658 0.067 Uiso 1 calc . . GR
H5B H 0.3178 0.5825 0.8490 0.067 Uiso 1 calc . . GR
H5C H 0.4692 0.5114 0.8294 0.067 Uiso 1 calc . . GR
C2 C 0.1999(10) 0.4330(4) 0.4231(7) 0.0374(14) Uani 1 d . . .
H2 H 0.1766 0.3783 0.3758 0.045 Uiso 1 calc . . R
C9 C 0.4884(11) 0.6965(5) 0.1592(10) 0.0504(18) Uani 1 d . . .
H9 H 0.5850 0.7034 0.1000 0.061 Uiso 1 calc . . R

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0443(4) 0.0315(4) 0.0368(4) 0.0022(2) 0.0088(3) 0.0012(3)
N2 0.045(3) 0.031(2) 0.031(2) -0.001(2) 0.005(2) 0.000(2)
N1 0.046(3) 0.036(3) 0.035(3) -0.001(2) 0.012(2) -0.003(2)
C1 0.036(3) 0.027(3) 0.036(3) -0.001(2) 0.010(2) 0.000(2)
C3 0.031(3) 0.032(3) 0.040(3) 0.008(3) 0.010(2) 0.002(2)
C8 0.046(4) 0.034(3) 0.042(3) 0.004(3) 0.001(3) 0.000(3)
C7 0.044(4) 0.034(3) 0.034(3) 0.001(2) 0.008(3) 0.004(3)
C6 0.033(3) 0.038(3) 0.037(3) -0.004(3) 0.008(2) -0.004(3)
C4 0.041(3) 0.037(3) 0.034(3) 0.004(3) 0.010(2) 0.003(3)
C5 0.048(4) 0.049(4) 0.039(3) 0.000(3) 0.013(3) -0.008(3)
C2 0.049(4) 0.028(3) 0.035(3) -0.002(2) 0.008(3) -0.002(3)
C9 0.049(4) 0.043(4) 0.061(5) 0.011(3) 0.014(4) 0.005(3)

_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
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N2 C1 1.330(8) . ?
N1 C1 1.359(8) . ?
N1 C7 1.481(8) . ?
N1 C6 1.384(9) . ?
C1 C2 1.428(9) . ?
C3 H3 0.9300 . ?
C3 C4 1.425(9) . ?
C3 C2 1.345(9) . ?
C8 C7 1.479(10) . ?
C8 C9 1.183(11) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C6 H6 0.9300 . ?
C6 C4 1.355(10) . ?
C4 C5 1.500(9) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C2 H2 0.9300 . ?
C9 H9 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
H2A N2 H2B 120.0 . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
C1 N1 C7 120.0(5) . . ?
C1 N1 C6 121.7(6) . . ?
C6 N1 C7 118.3(5) . . ?
N2 C1 N1 120.9(6) . . ?
N2 C1 C2 121.3(6) . . ?
N1 C1 C2 117.8(6) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.6(6) . . ?
C9 C8 C7 179.4(8) . . ?
N1 C7 H7A 109.6 . . ?
N1 C7 H7B 109.6 . . ?
C8 C7 N1 110.4(5) . . ?
C8 C7 H7A 109.6 . . ?
C8 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
N1 C6 H6 119.3 . . ?
C4 C6 N1 121.4(6) . . ?
C4 C6 H6 119.3 . . ?
C3 C4 C5 122.9(6) . . ?
C6 C4 C3 117.4(6) . . ?
C6 C4 C5 119.6(6) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 119.9(6) . . ?
C3 C2 H2 120.0 . . ?
C8 C9 H9 180.0 . . ?

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
N2 C1 C2 C3 179.2(6) . . . . ?
N1 C1 C2 C3 1.5(9) . . . . ?
N1 C6 C4 C3 1.4(10) . . . . ?
N1 C6 C4 C5 179.9(6) . . . . ?
C1 N1 C7 C8 -74.6(8) . . . . ?
C1 N1 C6 C4 -0.7(10) . . . . ?
C7 N1 C1 N2 2.2(9) . . . . ?
C7 N1 C1 C2 179.9(6) . . . . ?
C7 N1 C6 C4 178.6(6) . . . . ?
C6 N1 C1 N2 -178.5(6) . . . . ?
C6 N1 C1 C2 -0.8(9) . . . . ?
C6 N1 C7 C8 106.1(7) . . . . ?
C4 C3 C2 C1 -0.8(10) . . . . ?
C2 C3 C4 C6 -0.7(10) . . . . ?
C2 C3 C4 C5 -179.1(6) . . . . ?
C9 C8 C7 N1 -150(78) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-4 -5 0 0.0725 -4.1776 -4.8775 0.2531 0.2665 -0.7953 -0.5476
1 -3 5 0.0177 0.9898 -2.6780 5.3238 -0.3558 -0.5578 0.7500
4 5 -1 0.0943 4.0002 5.3157 -1.1487 -0.2059 0.8871 0.4199
-1 3 -5 0.0076 -0.8046 2.9023 -5.3463 0.3445 0.5946 -0.7270
1 7 4 0.0376 0.7475 6.9696 3.8616 -0.9536 0.1321 0.2778
5 -2 0 0.1442 4.6927 -1.9118 0.1099 0.2346 0.4132 0.8769
-1 -7 -4 0.0370 -0.8462 -6.9158 -3.8567 0.9468 -0.1407 -0.2960
-5 2 0 0.0696 -4.6854 2.0339 -0.0436 -0.2513 -0.4114 -0.8732

_olex2_date_sample_data_collection 2015-08-26
_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_mrc214
_database_code_depnum_ccdc_archive 'CCDC 1471648'
_audit_update_record             
;
2016-03-31 deposited with the CCDC.
2016-07-22 downloaded from the CCDC.
;
_audit_creation_date             2016-01-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        
'5-Iodo-2-amino-1-(2-propynyl)pyridinium bromide'
_chemical_formula_moiety         'C8 H8 I N2, Br'
_chemical_formula_sum            'C8 H8 Br I N2'
_chemical_formula_weight         338.97
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C32 H32 Br4 I4 N8'
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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      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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   6.0553(4)
_cell_length_b                   14.8323(10)
_cell_length_c                   12.4390(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.295(8)
_cell_angle_gamma                90.00
_cell_volume                     1087.24(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2422
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.5210
_cell_measurement_theta_min      3.4470
_exptl_absorpt_coefficient_mu    6.573
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77506
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light orange'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.071
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.2118
_exptl_crystal_size_mid          0.1382
_exptl_crystal_size_min          0.0712
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0691
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6777
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         31.25
_diffrn_reflns_theta_min         3.22
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3095
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.863
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    9.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       12.9509   37.0000  -60.0000 60

#__ type_ start__ end____ width___ exp.time_
  2 omega   -5.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       12.9509  -57.0000  -90.0000 40

#__ type_ start__ end____ width___ exp.time_
  3 omega  -40.00    1.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.7322  -57.0000  150.0000 41

#__ type_ start__ end____ width___ exp.time_
  4 omega  -32.00   39.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.7322   37.0000  150.0000 71
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0315509000
_diffrn_orient_matrix_UB_12      0.0271133000
_diffrn_orient_matrix_UB_13      0.0480656000
_diffrn_orient_matrix_UB_21      0.0045048000
_diffrn_orient_matrix_UB_22      0.0383670000
_diffrn_orient_matrix_UB_23      -0.0334220000
_diffrn_orient_matrix_UB_31      -0.1160498000
_diffrn_orient_matrix_UB_32      0.0088473000
_diffrn_orient_matrix_UB_33      -0.0021642000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2337
_reflns_number_total             3055
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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         1.256
_refine_diff_density_min         -0.740
_refine_diff_density_rms         0.197
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         3055
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0401
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0199P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0692
_refine_ls_wR_factor_ref         0.0781
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2), C3(H3)
2.c X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
2.d :
 C8(H8)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
_atom_site_refinement_flags_posn
I1 I 0.07973(4) 0.792582(19) 0.23360(3) 0.02040(10) Uani 1 d . . .
Br1 Br -0.27054(7) 0.93831(3) 0.30447(4) 0.02111(12) Uani 1 d . . .
N1 N 0.6352(6) 0.6148(2) 0.2194(3) 0.0176(8) Uani 1 d . . .
N2 N 0.7946(6) 0.5564(3) 0.0803(3) 0.0241(9) Uani 1 d . . .
H2A H 0.8930 0.5274 0.1289 0.029 Uiso 1 calc . . R
H2B H 0.7961 0.5522 0.0115 0.029 Uiso 1 calc . . R
C5 C 0.4755(7) 0.6677(3) 0.2524(4) 0.0205(10) Uani 1 d . . .
H5 H 0.4772 0.6723 0.3271 0.025 Uiso 1 calc . . R
C4 C 0.3171(7) 0.7129(3) 0.1782(4) 0.0199(10) Uani 1 d . . .
C1 C 0.6406(7) 0.6073(3) 0.1113(4) 0.0203(10) Uani 1 d . . .
C2 C 0.4738(7) 0.6538(3) 0.0324(4) 0.0235(10) Uani 1 d . . .
H2 H 0.4719 0.6491 -0.0423 0.028 Uiso 1 calc . . R
C6 C 0.7979(7) 0.5595(3) 0.3018(4) 0.0210(10) Uani 1 d . . .
H6A H 0.7847 0.4969 0.2784 0.025 Uiso 1 calc . . R
H6B H 0.9512 0.5791 0.3029 0.025 Uiso 1 calc . . R
C3 C 0.3158(8) 0.7053(3) 0.0660(4) 0.0254(11) Uani 1 d . . .
H3 H 0.2063 0.7357 0.0139 0.030 Uiso 1 calc . . R
C7 C 0.7614(7) 0.5654(3) 0.4135(4) 0.0254(11) Uani 1 d . . .
C8 C 0.7286(8) 0.5674(3) 0.5027(5) 0.0302(12) Uani 1 d . . .
H8 H 0.7026 0.5689 0.5735 0.036 Uiso 1 calc . . R

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.02211(15) 0.01974(16) 0.01967(18) -0.00085(13) 0.00550(12) 0.00229(11)
Br1 0.0215(2) 0.0266(3) 0.0164(3) -0.0009(2) 0.00686(18) 0.00139(18)
N1 0.0190(16) 0.0215(19) 0.011(2) -0.0009(16) 0.0019(15) -0.0005(15)
N2 0.0273(19) 0.033(2) 0.012(2) -0.0012(18) 0.0049(17) 0.0082(17)
C5 0.023(2) 0.021(2) 0.019(3) -0.006(2) 0.0095(19) -0.0025(19)
C4 0.024(2) 0.019(2) 0.017(3) -0.003(2) 0.0071(19) 0.0012(19)
C1 0.022(2) 0.020(2) 0.021(3) -0.001(2) 0.0090(19) -0.0006(19)
C2 0.033(2) 0.023(2) 0.016(3) 0.003(2) 0.008(2) 0.001(2)
C6 0.021(2) 0.022(2) 0.019(3) 0.002(2) 0.0044(19) 0.0038(19)
C3 0.028(2) 0.028(3) 0.020(3) 0.005(2) 0.006(2) 0.005(2)
C7 0.024(2) 0.030(3) 0.021(3) 0.000(2) 0.003(2) 0.001(2)
C8 0.027(2) 0.043(3) 0.019(3) 0.003(2) 0.002(2) 0.005(2)

_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
I1 C4 2.096(4) . ?
N1 C5 1.379(5) . ?
N1 C1 1.358(6) . ?
N1 C6 1.493(6) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N2 C1 1.324(5) . ?
C5 H5 0.9300 . ?
C5 C4 1.347(6) . ?
C4 C3 1.398(7) . ?
C1 C2 1.415(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.363(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.459(7) . ?
C3 H3 0.9300 . ?
C7 C8 1.171(7) . ?
C8 H8 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
C5 N1 C6 120.4(4) . . ?
C1 N1 C5 121.3(4) . . ?
C1 N1 C6 118.2(4) . . ?
H2A N2 H2B 120.0 . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
N1 C5 H5 119.4 . . ?
C4 C5 N1 121.2(5) . . ?
C4 C5 H5 119.4 . . ?
C5 C4 I1 119.3(4) . . ?
C5 C4 C3 118.9(4) . . ?
C3 C4 I1 121.8(3) . . ?
N1 C1 C2 118.1(4) . . ?
N2 C1 N1 121.0(4) . . ?
N2 C1 C2 120.9(5) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.0(5) . . ?
C3 C2 H2 120.0 . . ?
N1 C6 H6A 108.9 . . ?
N1 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C7 C6 N1 113.6(4) . . ?
C7 C6 H6A 108.9 . . ?
C7 C6 H6B 108.9 . . ?
C4 C3 H3 119.7 . . ?
C2 C3 C4 120.5(5) . . ?
C2 C3 H3 119.7 . . ?
C8 C7 C6 177.7(5) . . ?
C7 C8 H8 180.0 . . ?

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
I1 C4 C3 C2 179.3(3) . . . . ?
N1 C5 C4 I1 -179.8(3) . . . . ?
N1 C5 C4 C3 0.1(6) . . . . ?
N1 C1 C2 C3 1.0(6) . . . . ?
N1 C6 C7 C8 103(13) . . . . ?
N2 C1 C2 C3 179.5(4) . . . . ?
C5 N1 C1 N2 180.0(4) . . . . ?
C5 N1 C1 C2 -1.5(6) . . . . ?
C5 N1 C6 C7 2.4(6) . . . . ?
C5 C4 C3 C2 -0.6(7) . . . . ?
C1 N1 C5 C4 1.0(6) . . . . ?
C1 N1 C6 C7 -173.8(4) . . . . ?
C1 C2 C3 C4 0.1(7) . . . . ?
C6 N1 C5 C4 -175.2(4) . . . . ?
C6 N1 C1 N2 -3.8(6) . . . . ?
C6 N1 C1 C2 174.7(4) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
6 1 -16 0.0848 5.5309 1.4249 -15.5572 -0.5346 0.5995 -0.5956
-6 0 15 0.0093 -5.8335 -0.3601 15.2081 0.5372 -0.5484 0.6409
6 -15 0 0.0968 5.8876 -14.6405 0.4088 -0.1915 -0.5489 -0.8137
7 11 -2 0.0859 7.2791 10.8625 -2.4719 0.4054 0.5322 -0.7433
-5 10 13 0.0174 -5.3260 10.3694 12.8182 0.7292 -0.0546 0.6821
-8 -7 6 0.0259 -8.0248 -6.6259 5.9404 -0.1473 -0.4889 0.8598
5 -11 -13 0.0487 4.9031 -11.2617 -12.8316 -0.7674 0.0189 -0.6409
6 -3 8 0.1265 6.3229 -2.6399 8.2876 0.5263 -0.3498 -0.7751
-6 -11 11 0.0302 -6.1210 -11.0068 10.6921 0.0224 -0.8072 0.5898
-7 1 -6 0.0581 -7.1029 0.6455 -6.1084 -0.5002 0.1969 0.8432
6 11 -11 0.0617 6.0267 11.0829 -10.8663 -0.0317 0.8155 -0.5778

_olex2_date_sample_data_collection 2016-01-10
_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_mrc218
_database_code_depnum_ccdc_archive 'CCDC 1471649'
_audit_update_record             
;
2016-03-31 deposited with the CCDC.
2016-07-22 downloaded from the CCDC.
;
_audit_creation_date             2016-01-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        '6-Nitro-2-methylimidazo[1,2-a]pyridine '
_chemical_formula_moiety         'C8 H7 N3 O2'
_chemical_formula_sum            'C8 H7 N3 O2'
_chemical_formula_weight         177.17
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H10 N3 O2'
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'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-y, x-y, z'
3 '-x+y, -x, z'
4 'x+2/3, y+1/3, z+1/3'
5 '-y+2/3, x-y+1/3, z+1/3'
6 '-x+y+2/3, -x+1/3, z+1/3'
7 'x+1/3, y+2/3, z+2/3'
8 '-y+1/3, x-y+2/3, z+2/3'
9 '-x+y+1/3, -x+2/3, z+2/3'
10 '-x, -y, -z'
11 'y, -x+y, -z'
12 'x-y, x, -z'
13 '-x+2/3, -y+1/3, -z+1/3'
14 'y+2/3, -x+y+1/3, -z+1/3'
15 'x-y+2/3, x+1/3, -z+1/3'
16 '-x+1/3, -y+2/3, -z+2/3'
17 'y+1/3, -x+y+2/3, -z+2/3'
18 'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   24.304(2)
_cell_length_b                   24.304(2)
_cell_length_c                   6.8579(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     3508.1(5)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    2113
_cell_measurement_temperature    119.99(14)
_cell_measurement_theta_max      30.4590
_cell_measurement_theta_min      3.9140
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94186
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1656
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.0982
_exptl_crystal_size_min          0.0286
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4157
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         31.24
_diffrn_reflns_theta_min         3.12
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      119.99(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3095
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.854
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -16.00   46.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       13.1072   19.0000   90.0000 62

#__ type_ start__ end____ width___ exp.time_
  2 omega    3.00   57.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       13.1072   19.0000   30.0000 54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0105511000
_diffrn_orient_matrix_UB_12      -0.0251292000
_diffrn_orient_matrix_UB_13      0.0685678000
_diffrn_orient_matrix_UB_21      0.0312945000
_diffrn_orient_matrix_UB_22      0.0135108000
_diffrn_orient_matrix_UB_23      0.0375710000
_diffrn_orient_matrix_UB_31      -0.0066919000
_diffrn_orient_matrix_UB_32      0.0179315000
_diffrn_orient_matrix_UB_33      0.0677552000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1656
_reflns_number_total             2171
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_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         0.267
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         2171
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0526
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0530P)²+2.6989P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1269
_refine_ls_wR_factor_ref         0.1374
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C2(H2), C6(H6)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
_atom_site_refinement_flags_posn
O2 O 0.25580(6) 0.28922(6) 0.62655(19) 0.0303(3) Uani 1 d . . .
O1 O 0.15656(6) 0.22172(6) 0.6809(2) 0.0338(3) Uani 1 d . . .
N1 N 0.21550(6) 0.42759(6) 0.50885(19) 0.0174(3) Uani 1 d . . .
N2 N 0.15167(6) 0.46958(7) 0.48463(19) 0.0206(3) Uani 1 d . . .
N3 N 0.19961(7) 0.27484(7) 0.6347(2) 0.0222(3) Uani 1 d . . .
C1 C 0.15296(7) 0.41681(8) 0.5231(2) 0.0174(3) Uani 1 d . . .
C5 C 0.23074(8) 0.38182(8) 0.5435(2) 0.0187(3) Uani 1 d . . .
H5 H 0.2724 0.3903 0.5343 0.022 Uiso 1 calc . . R
C7 C 0.21370(8) 0.51488(8) 0.4444(2) 0.0196(3) Uani 1 d . . .
C4 C 0.18265(8) 0.32316(8) 0.5922(2) 0.0190(3) Uani 1 d . . .
C3 C 0.11835(8) 0.30819(8) 0.6085(2) 0.0199(4) Uani 1 d . . .
H3 H 0.0867 0.2674 0.6422 0.024 Uiso 1 calc . . R
C2 C 0.10414(8) 0.35494(8) 0.5734(2) 0.0203(3) Uani 1 d . . .
H2 H 0.0623 0.3462 0.5827 0.024 Uiso 1 calc . . R
C6 C 0.25358(8) 0.49066(8) 0.4584(2) 0.0199(3) Uani 1 d . . .
H6 H 0.2973 0.5122 0.4383 0.024 Uiso 1 calc . . R
C8 C 0.23129(9) 0.58146(8) 0.3943(3) 0.0260(4) Uani 1 d . . .
H8A H 0.2072 0.5812 0.2831 0.039 Uiso 1 calc . . GR
H8B H 0.2758 0.6055 0.3644 0.039 Uiso 1 calc . . GR
H8C H 0.2222 0.6005 0.5031 0.039 Uiso 1 calc . . GR

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O2 0.0301(7) 0.0326(7) 0.0370(8) 0.0036(6) 0.0031(5) 0.0222(6)
O1 0.0332(8) 0.0188(7) 0.0458(8) 0.0049(6) 0.0000(6) 0.0104(6)
N1 0.0156(6) 0.0185(7) 0.0179(6) -0.0008(5) -0.0004(5) 0.0083(5)
N2 0.0187(7) 0.0220(7) 0.0216(7) 0.0004(5) 0.0000(5) 0.0106(6)
N3 0.0270(8) 0.0216(7) 0.0205(7) -0.0018(5) -0.0016(6) 0.0140(6)
C1 0.0147(7) 0.0229(8) 0.0155(7) -0.0026(6) -0.0021(6) 0.0100(6)
C5 0.0181(8) 0.0227(8) 0.0183(7) -0.0015(6) -0.0010(6) 0.0126(7)
C7 0.0201(8) 0.0200(8) 0.0187(7) 0.0001(6) -0.0004(6) 0.0100(7)
C4 0.0233(8) 0.0197(8) 0.0160(7) -0.0011(6) -0.0008(6) 0.0123(7)
C3 0.0193(8) 0.0180(8) 0.0179(7) -0.0009(6) 0.0008(6) 0.0059(6)
C2 0.0153(8) 0.0234(8) 0.0195(8) -0.0021(6) 0.0003(6) 0.0077(7)
C6 0.0159(8) 0.0178(8) 0.0240(8) 0.0014(6) 0.0018(6) 0.0069(6)
C8 0.0242(9) 0.0222(9) 0.0326(9) 0.0045(7) 0.0028(7) 0.0124(7)

_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
O2 N3 1.2300(18) . ?
O1 N3 1.2291(19) . ?
N1 C1 1.411(2) . ?
N1 C5 1.358(2) . ?
N1 C6 1.381(2) . ?
N2 C1 1.325(2) . ?
N2 C7 1.379(2) . ?
N3 C4 1.455(2) . ?
C1 C2 1.416(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.358(2) . ?
C7 C6 1.366(2) . ?
C7 C8 1.493(2) . ?
C4 C3 1.421(2) . ?
C3 H3 0.9300 . ?
C3 C2 1.364(2) . ?
C2 H2 0.9300 . ?
C6 H6 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 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
C5 N1 C1 123.07(13) . . ?
C5 N1 C6 130.35(14) . . ?
C6 N1 C1 106.58(13) . . ?
C1 N2 C7 105.50(13) . . ?
O2 N3 C4 118.93(14) . . ?
O1 N3 O2 123.45(14) . . ?
O1 N3 C4 117.61(14) . . ?
N1 C1 C2 117.85(14) . . ?
N2 C1 N1 110.56(14) . . ?
N2 C1 C2 131.60(15) . . ?
N1 C5 H5 121.3 . . ?
N1 C5 C4 117.34(14) . . ?
C4 C5 H5 121.3 . . ?
N2 C7 C8 121.19(14) . . ?
C6 C7 N2 111.71(14) . . ?
C6 C7 C8 127.10(15) . . ?
C5 C4 N3 117.01(15) . . ?
C5 C4 C3 123.18(15) . . ?
C3 C4 N3 119.78(15) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 C4 118.50(15) . . ?
C2 C3 H3 120.7 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.06(15) . . ?
C3 C2 H2 120.0 . . ?
N1 C6 H6 127.2 . . ?
C7 C6 N1 105.66(14) . . ?
C7 C6 H6 127.2 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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
O2 N3 C4 C5 0.6(2) . . . . ?
O2 N3 C4 C3 -177.49(14) . . . . ?
O1 N3 C4 C5 179.29(14) . . . . ?
O1 N3 C4 C3 1.2(2) . . . . ?
N1 C1 C2 C3 0.7(2) . . . . ?
N1 C5 C4 N3 -178.26(13) . . . . ?
N1 C5 C4 C3 -0.2(2) . . . . ?
N2 C1 C2 C3 -179.26(16) . . . . ?
N2 C7 C6 N1 0.19(18) . . . . ?
N3 C4 C3 C2 178.04(14) . . . . ?
C1 N1 C5 C4 0.6(2) . . . . ?
C1 N1 C6 C7 -0.04(17) . . . . ?
C1 N2 C7 C6 -0.26(18) . . . . ?
C1 N2 C7 C8 -179.82(15) . . . . ?
C5 N1 C1 N2 179.07(13) . . . . ?
C5 N1 C1 C2 -0.9(2) . . . . ?
C5 N1 C6 C7 -179.16(15) . . . . ?
C5 C4 C3 C2 0.0(2) . . . . ?
C7 N2 C1 N1 0.23(17) . . . . ?
C7 N2 C1 C2 -179.82(16) . . . . ?
C4 C3 C2 C1 -0.3(2) . . . . ?
C6 N1 C1 N2 -0.12(17) . . . . ?
C6 N1 C1 C2 179.92(14) . . . . ?
C6 N1 C5 C4 179.62(15) . . . . ?
C8 C7 C6 N1 179.72(15) . . . . ?

_olex2_date_sample_data_collection 2016-01-25
_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_mrc2g
_database_code_depnum_ccdc_archive 'CCDC 1471650'
_audit_update_record             
;
2016-03-31 deposited with the CCDC.
2016-07-22 downloaded from the CCDC.
;
_audit_creation_date             2016-01-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        6-Bromo-2-methylimidazo[1,2-a]pyridine
_chemical_formula_moiety         'C8 H7 Br N2'
_chemical_formula_sum            'C8 H7 Br N2'
_chemical_formula_weight         211.07
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H10 N2 Br1'
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'
Br Br -0.6763 1.2805 '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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   3.9883(6)
_cell_length_b                   17.853(2)
_cell_length_c                   11.2011(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.622(11)
_cell_angle_gamma                90.00
_cell_volume                     797.27(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1361
_cell_measurement_temperature    120.01(16)
_cell_measurement_theta_max      72.5080
_cell_measurement_theta_min      4.6450
_exptl_absorpt_coefficient_mu    6.457
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40410
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.758
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.223
_exptl_crystal_size_mid          0.0777
_exptl_crystal_size_min          0.0292
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0828
_diffrn_reflns_av_unetI/netI     0.0702
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4773
_diffrn_reflns_theta_full        74.27
_diffrn_reflns_theta_max         74.27
_diffrn_reflns_theta_min         4.66
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(16)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3095
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   18.00   61.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0434  -57.0000  -30.0000 43

#__ type_ start__ end____ width___ exp.time_
  2 omega   20.00   48.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0434  -57.0000  -60.0000 28

#__ type_ start__ end____ width___ exp.time_
  3 omega   21.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0434  -62.0000 -129.4610 47

#__ type_ start__ end____ width___ exp.time_
  4 omega   53.00   95.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -65.0000 -121.0159 42

#__ type_ start__ end____ width___ exp.time_
  5 omega   59.00  106.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -65.0000  -67.6919 47

#__ type_ start__ end____ width___ exp.time_
  6 omega   60.00  136.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -65.0000  -15.1881 76

#__ type_ start__ end____ width___ exp.time_
  7 omega   71.00  105.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -64.0000   30.9583 34

#__ type_ start__ end____ width___ exp.time_
  8 omega   67.00   92.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -62.0000   65.0330 25

#__ type_ start__ end____ width___ exp.time_
  9 omega   55.00   90.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -30.0000   90.0000 35

#__ type_ start__ end____ width___ exp.time_
 10 omega   66.00  106.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -64.0000  167.3480 40

#__ type_ start__ end____ width___ exp.time_
 11 omega   33.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0434  -57.0000   90.0000 35

#__ type_ start__ end____ width___ exp.time_
 12 omega   25.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0434  -62.0000   65.2653 41

#__ type_ start__ end____ width___ exp.time_
 13 omega   82.00  160.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   30.0000  150.0000 78

#__ type_ start__ end____ width___ exp.time_
 14 omega   42.00  105.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -65.0000  116.7107 63

#__ type_ start__ end____ width___ exp.time_
 15 omega   26.00  155.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -15.0000  -60.0000 129

#__ type_ start__ end____ width___ exp.time_
 16 omega   79.00  114.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   30.0000 -120.0000 35

#__ type_ start__ end____ width___ exp.time_
 17 omega   35.00   86.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -30.0000 -120.0000 51

#__ type_ start__ end____ width___ exp.time_
 18 omega   37.00   89.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -30.0000 -180.0000 52

#__ type_ start__ end____ width___ exp.time_
 19 omega   -1.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0434  -57.0000 -180.0000 66

#__ type_ start__ end____ width___ exp.time_
 20 omega  -47.00   30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0434   37.0000  120.0000 77

#__ type_ start__ end____ width___ exp.time_
 21 omega  -79.00   30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0434   19.0000   60.0000 109
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1804102000
_diffrn_orient_matrix_UB_12      -0.0254331000
_diffrn_orient_matrix_UB_13      0.1165861000
_diffrn_orient_matrix_UB_21      0.3387767000
_diffrn_orient_matrix_UB_22      0.0240636000
_diffrn_orient_matrix_UB_23      -0.0504402000
_diffrn_orient_matrix_UB_31      -0.0455250000
_diffrn_orient_matrix_UB_32      0.0788328000
_diffrn_orient_matrix_UB_33      0.0529177000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1261
_reflns_number_total             1576
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_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         1.883
_refine_diff_density_min         -1.091
_refine_diff_density_rms         0.205
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1576
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0667
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1081P)²+1.2883P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1730
_refine_ls_wR_factor_ref         0.1847
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C6(H6), C2(H2)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
_atom_site_refinement_flags_posn
Br1 Br 0.73612(18) 0.51183(4) 0.26251(6) 0.0359(3) Uani 1 d . . .
N1 N 0.3147(14) 0.7089(3) 0.3688(4) 0.0276(11) Uani 1 d . . .
N2 N 0.2480(15) 0.7755(3) 0.5368(5) 0.0326(12) Uani 1 d . . .
C4 C 0.5874(16) 0.5940(3) 0.3556(6) 0.0301(13) Uani 1 d . . .
C1 C 0.3778(17) 0.7133(3) 0.4913(5) 0.0271(12) Uani 1 d . . .
C7 C 0.1071(17) 0.8129(3) 0.4409(6) 0.0310(13) Uani 1 d . . .
C5 C 0.4205(17) 0.6498(3) 0.3004(5) 0.0298(13) Uani 1 d . . .
H5 H 0.3775 0.6487 0.2184 0.036 Uiso 1 calc . . R
C3 C 0.6608(17) 0.5944(4) 0.4807(6) 0.0322(14) Uani 1 d . . .
H3 H 0.7805 0.5553 0.5166 0.039 Uiso 1 calc . . R
C6 C 0.1418(18) 0.7729(4) 0.3371(6) 0.0332(14) Uani 1 d . . .
H6 H 0.0642 0.7863 0.2610 0.040 Uiso 1 calc . . R
C2 C 0.5525(18) 0.6528(3) 0.5464(5) 0.0336(14) Uani 1 d . . .
H2 H 0.5933 0.6533 0.6286 0.040 Uiso 1 calc . . R
C8 C -0.0637(19) 0.8864(4) 0.4566(6) 0.0383(15) Uani 1 d . . .
H8A H -0.2404 0.8808 0.5124 0.057 Uiso 1 calc . . GR
H8B H -0.1564 0.9030 0.3811 0.057 Uiso 1 calc . . GR
H8C H 0.0956 0.9226 0.4865 0.057 Uiso 1 calc . . GR

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0498(5) 0.0209(4) 0.0372(5) -0.0025(2) 0.0053(3) 0.0017(3)
N1 0.037(3) 0.021(2) 0.025(2) 0.0021(19) 0.0006(19) 0.001(2)
N2 0.051(3) 0.021(2) 0.025(2) -0.0007(19) 0.003(2) -0.003(2)
C4 0.036(3) 0.021(3) 0.033(3) 0.001(2) 0.005(2) -0.008(2)
C1 0.040(3) 0.017(3) 0.025(3) 0.000(2) 0.005(2) -0.006(2)
C7 0.042(4) 0.018(3) 0.033(3) 0.001(2) 0.007(2) -0.005(2)
C5 0.039(3) 0.024(3) 0.026(3) -0.001(2) 0.002(2) -0.004(2)
C3 0.044(4) 0.021(3) 0.031(3) 0.007(2) -0.003(3) -0.002(2)
C6 0.049(4) 0.022(3) 0.029(3) 0.004(2) 0.001(3) 0.001(3)
C2 0.051(4) 0.023(3) 0.027(3) 0.002(2) -0.004(3) -0.006(3)
C8 0.048(4) 0.030(3) 0.037(3) 0.002(3) 0.008(3) -0.001(3)

_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
Br1 C4 1.904(6) . ?
N1 C1 1.391(8) . ?
N1 C5 1.377(8) . ?
N1 C6 1.376(8) . ?
N2 C1 1.333(9) . ?
N2 C7 1.372(8) . ?
C4 C5 1.340(9) . ?
C4 C3 1.424(9) . ?
C1 C2 1.417(9) . ?
C7 C6 1.375(9) . ?
C7 C8 1.490(9) . ?
C5 H5 0.9300 . ?
C3 H3 0.9300 . ?
C3 C2 1.355(9) . ?
C6 H6 0.9300 . ?
C2 H2 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 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
C5 N1 C1 122.9(5) . . ?
C6 N1 C1 106.4(5) . . ?
C6 N1 C5 130.7(5) . . ?
C1 N2 C7 105.1(5) . . ?
C5 C4 Br1 118.6(5) . . ?
C5 C4 C3 122.4(6) . . ?
C3 C4 Br1 119.0(5) . . ?
N1 C1 C2 117.4(5) . . ?
N2 C1 N1 111.3(5) . . ?
N2 C1 C2 131.3(6) . . ?
N2 C7 C6 111.1(6) . . ?
N2 C7 C8 120.9(6) . . ?
C6 C7 C8 127.9(6) . . ?
N1 C5 H5 121.0 . . ?
C4 C5 N1 118.0(6) . . ?
C4 C5 H5 121.0 . . ?
C4 C3 H3 120.7 . . ?
C2 C3 C4 118.6(6) . . ?
C2 C3 H3 120.7 . . ?
N1 C6 H6 127.0 . . ?
C7 C6 N1 106.0(5) . . ?
C7 C6 H6 127.0 . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.7(6) . . ?
C3 C2 H2 119.6 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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
Br1 C4 C5 N1 -180.0(4) . . . . ?
Br1 C4 C3 C2 -179.6(5) . . . . ?
N1 C1 C2 C3 1.8(10) . . . . ?
N2 C1 C2 C3 179.6(7) . . . . ?
N2 C7 C6 N1 -1.0(8) . . . . ?
C4 C3 C2 C1 -1.7(10) . . . . ?
C1 N1 C5 C4 0.9(9) . . . . ?
C1 N1 C6 C7 -0.1(7) . . . . ?
C1 N2 C7 C6 1.7(7) . . . . ?
C1 N2 C7 C8 -179.7(6) . . . . ?
C7 N2 C1 N1 -1.8(7) . . . . ?
C7 N2 C1 C2 -179.6(7) . . . . ?
C5 N1 C1 N2 -179.6(6) . . . . ?
C5 N1 C1 C2 -1.4(9) . . . . ?
C5 N1 C6 C7 -179.2(6) . . . . ?
C5 C4 C3 C2 1.1(10) . . . . ?
C3 C4 C5 N1 -0.7(9) . . . . ?
C6 N1 C1 N2 1.2(7) . . . . ?
C6 N1 C1 C2 179.4(6) . . . . ?
C6 N1 C5 C4 179.9(6) . . . . ?
C8 C7 C6 N1 -179.4(6) . . . . ?

_olex2_date_sample_data_collection 2016-01-12
_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_mrc196
_database_code_depnum_ccdc_archive 'CCDC 1471653'
_audit_update_record             
;
2016-03-31 deposited with the CCDC.
2016-07-22 downloaded from the CCDC.
;
_audit_creation_date             2016-01-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        
8-Chloro-6-trifluoromethyl-2-methylimidazo[1,2-a]pyridine
_chemical_formula_moiety         'C9 H6 Cl F3 N2'
_chemical_formula_sum            'C9 H6 Cl F3 N2'
_chemical_formula_weight         234.61
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H10 N3 F3 Cl'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y, -z'
3 'x+1/2, y+1/2, z+1/2'
4 '-x+1, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, -y, z'
7 '-x+1/2, -y+1/2, -z+1/2'
8 'x, -y+1/2, z+1/2'

_cell_length_a                   12.0869(14)
_cell_length_b                   8.1608(10)
_cell_length_c                   19.776(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.192(12)
_cell_angle_gamma                90.00
_cell_volume                     1906.7(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1302
_cell_measurement_temperature    120.01(15)
_cell_measurement_theta_max      28.8020
_cell_measurement_theta_min      3.4480
_exptl_absorpt_coefficient_mu    0.411
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73299
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.635
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.1011
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_unetI/netI     0.0780
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            6222
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         31.20
_diffrn_reflns_theta_min         3.03
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(15)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3095
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.873
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -9.00   39.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       13.1072   57.0000 -120.0000 48

#__ type_ start__ end____ width___ exp.time_
  2 omega   26.00   80.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       13.1072   57.0000  -90.0000 54

#__ type_ start__ end____ width___ exp.time_
  3 omega   -3.00   84.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       13.1072   37.0000  150.0000 87

#__ type_ start__ end____ width___ exp.time_
  4 omega   12.00   56.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       13.1072   37.0000   30.0000 44
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0287979000
_diffrn_orient_matrix_UB_12      -0.0381803000
_diffrn_orient_matrix_UB_13      0.0309546000
_diffrn_orient_matrix_UB_21      -0.0281978000
_diffrn_orient_matrix_UB_22      -0.0747560000
_diffrn_orient_matrix_UB_23      -0.0108000000
_diffrn_orient_matrix_UB_31      0.0444602000
_diffrn_orient_matrix_UB_32      -0.0225906000
_diffrn_orient_matrix_UB_33      -0.0164867000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1933
_reflns_number_total             2707
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_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         0.324
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2707
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1075
_refine_ls_R_factor_gt           0.0707
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0468P)²+1.7036P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1274
_refine_ls_wR_factor_ref         0.1426
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
_atom_site_refinement_flags_posn
Cl1 Cl 0.13063(6) 0.72941(10) 0.39425(4) 0.0306(2) Uani 1 d . . .
F2 F 0.57697(15) 0.6656(3) 0.50855(9) 0.0467(6) Uani 1 d . . .
F3 F 0.66151(14) 0.6843(3) 0.42439(10) 0.0522(6) Uani 1 d . . .
F1 F 0.58094(17) 0.8940(2) 0.45757(12) 0.0595(7) Uani 1 d . . .
N1 N 0.36341(17) 0.5654(3) 0.29596(10) 0.0183(5) Uani 1 d . . .
N2 N 0.17439(18) 0.5359(3) 0.26490(11) 0.0206(5) Uani 1 d . . .
C1 C 0.2587(2) 0.5966(3) 0.31233(12) 0.0183(5) Uani 1 d . . .
C3 C 0.3582(2) 0.7276(3) 0.41673(13) 0.0223(6) Uani 1 d . . .
H3 H 0.3577 0.7826 0.4579 0.027 Uiso 1 calc . . R
C8 C 0.2263(2) 0.4639(3) 0.21650(13) 0.0221(6) Uani 1 d . . .
C6 C 0.4646(2) 0.6106(3) 0.33755(13) 0.0220(6) Uani 1 d . . .
H6 H 0.5328 0.5880 0.3248 0.026 Uiso 1 calc . . R
C4 C 0.4625(2) 0.6892(3) 0.39777(13) 0.0217(6) Uani 1 d . . .
C7 C 0.3410(2) 0.4798(3) 0.23445(13) 0.0218(6) Uani 1 d . . .
H7 H 0.3935 0.4409 0.2101 0.026 Uiso 1 calc . . R
C2 C 0.2598(2) 0.6832(3) 0.37428(13) 0.0208(6) Uani 1 d . . .
C5 C 0.5701(2) 0.7330(4) 0.44651(15) 0.0290(7) Uani 1 d . . .
C9 C 0.1576(2) 0.3789(4) 0.15473(14) 0.0316(7) Uani 1 d . . .
H9A H 0.1413 0.2691 0.1671 0.047 Uiso 1 calc . . GR
H9B H 0.1994 0.3756 0.1185 0.047 Uiso 1 calc . . GR
H9C H 0.0880 0.4373 0.1389 0.047 Uiso 1 calc . . GR

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0235(3) 0.0428(5) 0.0285(4) -0.0074(3) 0.0129(3) 0.0025(3)
F2 0.0353(10) 0.0726(15) 0.0261(9) 0.0098(10) -0.0070(8) -0.0135(10)
F3 0.0184(9) 0.0899(17) 0.0470(11) -0.0183(11) 0.0040(8) -0.0089(9)
F1 0.0536(12) 0.0318(12) 0.0764(15) -0.0046(11) -0.0244(11) -0.0116(10)
N1 0.0184(10) 0.0207(12) 0.0172(10) -0.0003(9) 0.0069(8) 0.0003(9)
N2 0.0209(11) 0.0225(12) 0.0183(11) 0.0005(9) 0.0038(9) -0.0009(9)
C1 0.0193(12) 0.0203(14) 0.0165(12) 0.0021(11) 0.0064(10) 0.0008(10)
C3 0.0274(14) 0.0223(14) 0.0183(12) -0.0007(11) 0.0069(11) -0.0006(12)
C8 0.0256(14) 0.0213(14) 0.0189(13) 0.0009(11) 0.0037(11) -0.0006(11)
C6 0.0178(12) 0.0237(15) 0.0251(13) 0.0033(12) 0.0059(10) 0.0018(11)
C4 0.0216(13) 0.0236(15) 0.0195(13) 0.0025(11) 0.0032(10) -0.0027(11)
C7 0.0263(14) 0.0220(14) 0.0183(12) -0.0027(11) 0.0075(11) 0.0032(11)
C2 0.0188(13) 0.0239(15) 0.0214(13) 0.0012(11) 0.0081(10) 0.0003(10)
C5 0.0245(14) 0.0334(17) 0.0269(14) 0.0001(14) 0.0008(12) -0.0061(12)
C9 0.0288(15) 0.0378(18) 0.0264(14) -0.0080(14) 0.0020(12) -0.0018(13)

_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 C2 1.731(3) . ?
F2 C5 1.331(3) . ?
F3 C5 1.332(3) . ?
F1 C5 1.334(4) . ?
N1 C1 1.395(3) . ?
N1 C6 1.372(3) . ?
N1 C7 1.379(3) . ?
N2 C1 1.327(3) . ?
N2 C8 1.381(3) . ?
C1 C2 1.412(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.425(4) . ?
C3 C2 1.353(4) . ?
C8 C7 1.362(4) . ?
C8 C9 1.495(4) . ?
C6 H6 0.9300 . ?
C6 C4 1.357(4) . ?
C4 C5 1.489(4) . ?
C7 H7 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 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
C6 N1 C1 123.3(2) . . ?
C6 N1 C7 130.5(2) . . ?
C7 N1 C1 106.2(2) . . ?
C1 N2 C8 104.8(2) . . ?
N1 C1 C2 116.8(2) . . ?
N2 C1 N1 111.5(2) . . ?
N2 C1 C2 131.7(2) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.3(2) . . ?
N2 C8 C9 120.6(2) . . ?
C7 C8 N2 111.4(2) . . ?
C7 C8 C9 128.0(2) . . ?
N1 C6 H6 120.9 . . ?
C4 C6 N1 118.3(2) . . ?
C4 C6 H6 120.9 . . ?
C3 C4 C5 118.5(2) . . ?
C6 C4 C3 121.1(2) . . ?
C6 C4 C5 120.4(2) . . ?
N1 C7 H7 126.9 . . ?
C8 C7 N1 106.1(2) . . ?
C8 C7 H7 126.9 . . ?
C1 C2 Cl1 117.61(19) . . ?
C3 C2 Cl1 121.1(2) . . ?
C3 C2 C1 121.2(2) . . ?
F2 C5 F3 106.5(2) . . ?
F2 C5 F1 105.7(2) . . ?
F2 C5 C4 111.9(2) . . ?
F3 C5 F1 106.7(2) . . ?
F3 C5 C4 112.8(2) . . ?
F1 C5 C4 112.6(2) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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 C1 C2 Cl1 177.89(19) . . . . ?
N1 C1 C2 C3 -2.5(4) . . . . ?
N1 C6 C4 C3 -1.5(4) . . . . ?
N1 C6 C4 C5 176.7(2) . . . . ?
N2 C1 C2 Cl1 -2.6(4) . . . . ?
N2 C1 C2 C3 177.1(3) . . . . ?
N2 C8 C7 N1 -0.4(3) . . . . ?
C1 N1 C6 C4 0.3(4) . . . . ?
C1 N1 C7 C8 0.2(3) . . . . ?
C1 N2 C8 C7 0.3(3) . . . . ?
C1 N2 C8 C9 179.1(3) . . . . ?
C3 C4 C5 F2 57.0(4) . . . . ?
C3 C4 C5 F3 177.2(3) . . . . ?
C3 C4 C5 F1 -61.9(3) . . . . ?
C8 N2 C1 N1 -0.2(3) . . . . ?
C8 N2 C1 C2 -179.7(3) . . . . ?
C6 N1 C1 N2 -177.9(2) . . . . ?
C6 N1 C1 C2 1.7(4) . . . . ?
C6 N1 C7 C8 177.9(3) . . . . ?
C6 C4 C5 F2 -121.3(3) . . . . ?
C6 C4 C5 F3 -1.1(4) . . . . ?
C6 C4 C5 F1 119.8(3) . . . . ?
C4 C3 C2 Cl1 -179.1(2) . . . . ?
C4 C3 C2 C1 1.3(4) . . . . ?
C7 N1 C1 N2 0.0(3) . . . . ?
C7 N1 C1 C2 179.6(2) . . . . ?
C7 N1 C6 C4 -177.1(3) . . . . ?
C2 C3 C4 C6 0.8(4) . . . . ?
C2 C3 C4 C5 -177.5(3) . . . . ?
C9 C8 C7 N1 -179.0(3) . . . . ?

_olex2_date_sample_data_collection 2016-01-25
_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_mrc207
_database_code_depnum_ccdc_archive 'CCDC 1471654'
_audit_update_record             
;
2016-03-31 deposited with the CCDC.
2016-07-22 downloaded from the CCDC.
;
_audit_creation_date             2015-05-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
'(N-Methyl)-2,7-dimethylimidazo[1,2-a]pyridinium iodide '
_chemical_formula_moiety         'I, C9 H10 Br N2'
_chemical_formula_sum            'C9 H10 Br I N2'
_chemical_formula_weight         353.00
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C72 H80 Br8 I8 N16'
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   16.4865(9)
_cell_length_b                   10.7791(5)
_cell_length_c                   13.0845(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.686(6)
_cell_angle_gamma                90.00
_cell_volume                     2175.3(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2386
_cell_measurement_temperature    120.00(13)
_cell_measurement_theta_max      30.1700
_cell_measurement_theta_min      3.6110
_exptl_absorpt_coefficient_mu    6.575
_exptl_absorpt_correction_T_max  0.695
_exptl_absorpt_correction_T_min  0.572
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.156
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1328
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_unetI/netI     0.0687
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7183
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         31.21
_diffrn_reflns_theta_min         3.10
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3095
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.877
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -7.00   84.00   1.0000    7.5300
omega____ theta____ kappa____ phi______ frames
    -       13.1072   37.0000   60.0000 91

#__ type_ start__ end____ width___ exp.time_
  2 omega  -15.00   34.00   1.0000    7.5300
omega____ theta____ kappa____ phi______ frames
    -       13.1072  -37.0000 -120.0000 49

#__ type_ start__ end____ width___ exp.time_
  3 omega  -27.00    5.00   1.0000    7.5300
omega____ theta____ kappa____ phi______ frames
    -       13.1072  -19.0000  -90.0000 32

#__ type_ start__ end____ width___ exp.time_
  4 omega  -12.00   14.00   1.0000    7.5300
omega____ theta____ kappa____ phi______ frames
    -       13.1072   19.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega  -61.00  -29.00   1.0000    7.5300
omega____ theta____ kappa____ phi______ frames
    -       13.1072  -19.0000  -90.0000 32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0287965000
_diffrn_orient_matrix_UB_12      0.0006007000
_diffrn_orient_matrix_UB_13      0.0295931000
_diffrn_orient_matrix_UB_21      -0.0312355000
_diffrn_orient_matrix_UB_22      0.0314781000
_diffrn_orient_matrix_UB_23      -0.0438760000
_diffrn_orient_matrix_UB_31      -0.0174916000
_diffrn_orient_matrix_UB_32      -0.0577659000
_diffrn_orient_matrix_UB_33      -0.0235529000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2528
_reflns_number_total             3102
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         1.074
_refine_diff_density_min         -0.697
_refine_diff_density_rms         0.188
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         3102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0432
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0192P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0819
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C9(H9), C6(H6)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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
_atom_site_refinement_flags_posn
I1 I 0.28976(2) 0.94853(2) 0.00700(2) 0.02342(10) Uani 1 d . . .
Br1 Br 0.58162(3) 0.21421(4) 0.40170(3) 0.01911(12) Uani 1 d . . .
N1 N 0.5030(2) 0.5763(3) 0.3753(2) 0.0136(7) Uani 1 d . . .
N2 N 0.3847(2) 0.6881(3) 0.3320(3) 0.0178(8) Uani 1 d . . .
C2 C 0.2939(3) 0.7231(4) 0.3007(4) 0.0253(10) Uani 1 d . . .
H2A H 0.2895 0.8006 0.3345 0.038 Uiso 1 calc . . GR
H2B H 0.2632 0.6602 0.3242 0.038 Uiso 1 calc . . GR
H2C H 0.2691 0.7316 0.2227 0.038 Uiso 1 calc . . GR
C5 C 0.5279(3) 0.6994(3) 0.3837(3) 0.0169(9) Uani 1 d . . .
H5 H 0.5844 0.7292 0.4044 0.020 Uiso 1 calc . . R
C4 C 0.4435(3) 0.9064(4) 0.3477(3) 0.0220(10) Uani 1 d . . .
H4A H 0.4108 0.9286 0.2735 0.033 Uiso 1 calc . . GR
H4B H 0.4994 0.9455 0.3700 0.033 Uiso 1 calc . . GR
H4C H 0.4132 0.9334 0.3942 0.033 Uiso 1 calc . . GR
C3 C 0.4548(3) 0.7686(4) 0.3562(3) 0.0173(9) Uani 1 d . . .
C8 C 0.4219(3) 0.3502(4) 0.3506(3) 0.0188(9) Uani 1 d . . .
H8 H 0.3960 0.2727 0.3448 0.023 Uiso 1 calc . . R
C7 C 0.5125(3) 0.3592(4) 0.3787(3) 0.0158(8) Uani 1 d . . .
C9 C 0.3716(3) 0.4559(4) 0.3317(3) 0.0181(9) Uani 1 d . . .
H9 H 0.3117 0.4516 0.3118 0.022 Uiso 1 calc . . R
C6 C 0.5530(3) 0.4710(4) 0.3927(3) 0.0167(9) Uani 1 d . . .
H6 H 0.6130 0.4761 0.4136 0.020 Uiso 1 calc . . R
C1 C 0.4147(3) 0.5704(4) 0.3436(3) 0.0141(8) Uani 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.01265(16) 0.02221(15) 0.03332(18) 0.00229(12) 0.00555(12) -0.00086(11)
Br1 0.0190(3) 0.0192(2) 0.0183(2) 0.00036(16) 0.00571(17) 0.00384(17)
N1 0.0095(18) 0.0203(16) 0.0104(15) 0.0001(13) 0.0028(13) 0.0001(14)
N2 0.013(2) 0.0219(17) 0.0185(17) 0.0007(14) 0.0059(15) 0.0024(14)
C2 0.014(3) 0.029(2) 0.030(2) -0.0042(19) 0.0034(19) 0.0026(19)
C5 0.017(2) 0.0181(19) 0.0176(19) -0.0001(16) 0.0083(17) -0.0022(17)
C4 0.029(3) 0.0191(19) 0.022(2) 0.0006(18) 0.014(2) -0.0007(19)
C3 0.018(2) 0.020(2) 0.0149(19) -0.0013(17) 0.0061(17) 0.0001(17)
C8 0.021(3) 0.021(2) 0.0140(19) -0.0036(16) 0.0049(17) -0.0050(17)
C7 0.015(2) 0.020(2) 0.0123(17) -0.0021(16) 0.0049(16) 0.0013(16)
C9 0.011(2) 0.023(2) 0.019(2) -0.0019(17) 0.0039(17) -0.0046(17)
C6 0.012(2) 0.023(2) 0.0138(19) -0.0018(16) 0.0034(16) 0.0005(17)
C1 0.009(2) 0.021(2) 0.0112(18) -0.0026(15) 0.0028(15) 0.0035(16)

_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
Br1 C7 1.894(4) . ?
N1 C5 1.382(5) . ?
N1 C6 1.374(5) . ?
N1 C1 1.367(5) . ?
N2 C2 1.455(6) . ?
N2 C3 1.389(5) . ?
N2 C1 1.351(5) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C5 H5 0.9300 . ?
C5 C3 1.354(6) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C4 C3 1.496(5) . ?
C8 H8 0.9300 . ?
C8 C7 1.409(6) . ?
C8 C9 1.379(6) . ?
C7 C6 1.358(6) . ?
C9 H9 0.9300 . ?
C9 C1 1.404(5) . ?
C6 H6 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
C6 N1 C5 129.5(4) . . ?
C1 N1 C5 108.9(3) . . ?
C1 N1 C6 121.6(3) . . ?
C3 N2 C2 126.3(3) . . ?
C1 N2 C2 125.1(4) . . ?
C1 N2 C3 108.6(4) . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C5 H5 126.4 . . ?
C3 C5 N1 107.2(4) . . ?
C3 C5 H5 126.4 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
N2 C3 C4 122.1(4) . . ?
C5 C3 N2 107.9(4) . . ?
C5 C3 C4 129.9(4) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C9 C8 C7 120.3(4) . . ?
C8 C7 Br1 120.5(3) . . ?
C6 C7 Br1 118.1(3) . . ?
C6 C7 C8 121.4(4) . . ?
C8 C9 H9 121.4 . . ?
C8 C9 C1 117.2(4) . . ?
C1 C9 H9 121.4 . . ?
N1 C6 H6 120.9 . . ?
C7 C6 N1 118.3(4) . . ?
C7 C6 H6 120.9 . . ?
N1 C1 C9 121.2(4) . . ?
N2 C1 N1 107.4(3) . . ?
N2 C1 C9 131.5(4) . . ?

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
Br1 C7 C6 N1 179.5(3) . . . . ?
N1 C5 C3 N2 0.7(4) . . . . ?
N1 C5 C3 C4 -177.8(4) . . . . ?
C2 N2 C3 C5 178.7(4) . . . . ?
C2 N2 C3 C4 -2.8(6) . . . . ?
C2 N2 C1 N1 -179.0(4) . . . . ?
C2 N2 C1 C9 -1.0(7) . . . . ?
C5 N1 C6 C7 -179.8(4) . . . . ?
C5 N1 C1 N2 0.1(4) . . . . ?
C5 N1 C1 C9 -178.1(4) . . . . ?
C3 N2 C1 N1 0.3(4) . . . . ?
C3 N2 C1 C9 178.3(4) . . . . ?
C8 C7 C6 N1 -2.1(6) . . . . ?
C8 C9 C1 N1 -1.6(6) . . . . ?
C8 C9 C1 N2 -179.4(4) . . . . ?
C7 C8 C9 C1 -1.1(6) . . . . ?
C9 C8 C7 Br1 -178.6(3) . . . . ?
C9 C8 C7 C6 3.1(6) . . . . ?
C6 N1 C5 C3 178.8(4) . . . . ?
C6 N1 C1 N2 -179.2(3) . . . . ?
C6 N1 C1 C9 2.6(6) . . . . ?
C1 N1 C5 C3 -0.5(4) . . . . ?
C1 N1 C6 C7 -0.7(6) . . . . ?
C1 N2 C3 C5 -0.6(4) . . . . ?
C1 N2 C3 C4 178.0(3) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-17 -10 1 0.0125 -17.1473 -9.7516 1.2915 0.5261 0.1720 0.8328
2 15 -2 0.0549 1.6807 15.1219 -1.6111 -0.0870 0.4942 -0.8650
13 -4 -17 0.0638 12.9684 -3.7330 -17.2906 -0.8874 0.2361 0.3960
-4 -15 4 0.0381 -3.5495 -14.7590 4.0957 0.2145 -0.5334 0.8182
12 -12 3 0.0359 12.0867 -11.5221 3.4943 -0.2516 -0.8935 0.3719
-21 2 -2 0.0223 -20.5616 2.3812 -1.8839 0.5378 0.7999 0.2665
17 10 0 0.0524 16.7448 9.7821 -0.3078 -0.4854 -0.2016 -0.8507
-15 -11 0 0.0246 -14.5659 -11.3020 0.1493 0.4171 0.0927 0.9041
1 -7 15 0.0230 1.2405 -7.4678 14.6594 0.3936 -0.9170 0.0644
15 11 0 0.0591 14.6013 11.2352 0.0143 -0.4133 -0.1030 -0.9047

_olex2_date_sample_data_collection 2015-05-06
_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_mrc227
_database_code_depnum_ccdc_archive 'CCDC 1471655'
_audit_update_record             
;
2016-03-31 deposited with the CCDC.
2016-07-22 downloaded from the CCDC.
;
_audit_creation_date             2015-05-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
'(N-Benzyl)-8-chloro-6-trifluoromethyl-2-methylimidazo[1,2-a]pyridinium bromide'
_chemical_formula_moiety         'Br, C16 H13 Cl F3 N2'
_chemical_formula_sum            'C16 H13 Br Cl F3 N2'
_chemical_formula_weight         405.64
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C256 H208 Br16 Cl16 F48 N32'
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'
Br Br -0.2901 2.4595 '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'
F F 0.0171 0.0103 '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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y, -z'
3 'x+1/2, y+1/2, z+1/2'
4 '-x+1, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, -y, z'
7 '-x+1/2, -y+1/2, -z+1/2'
8 'x, -y+1/2, z+1/2'

_cell_length_a                   22.7475(15)
_cell_length_b                   11.3014(7)
_cell_length_c                   27.0251(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.181(6)
_cell_angle_gamma                90.00
_cell_volume                     6735.8(7)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    5705
_cell_measurement_temperature    120.02(16)
_cell_measurement_theta_max      29.6100
_cell_measurement_theta_min      3.1630
_exptl_absorpt_coefficient_mu    2.628
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3232
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_min          0.051
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_av_unetI/netI     0.0993
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            26483
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         31.15
_diffrn_reflns_theta_min         2.69
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.02(16)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3095
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.887
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -6.00   42.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -       12.9509   37.0000  -60.0000 48

#__ type_ start__ end____ width___ exp.time_
  2 omega  -20.00   15.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -       12.9509   19.0000 -180.0000 35

#__ type_ start__ end____ width___ exp.time_
  3 omega   45.00   81.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -       12.9509   19.0000 -180.0000 36

#__ type_ start__ end____ width___ exp.time_
  4 omega  -40.00   31.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -       12.9509  -57.0000  -90.0000 71

#__ type_ start__ end____ width___ exp.time_
  5 omega  -24.00    3.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -       12.9509  -57.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
  6 omega  -67.00  -15.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.7322  -57.0000  150.0000 52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0231324000
_diffrn_orient_matrix_UB_12      0.0302730000
_diffrn_orient_matrix_UB_13      0.0179196000
_diffrn_orient_matrix_UB_21      -0.0042132000
_diffrn_orient_matrix_UB_22      0.0502924000
_diffrn_orient_matrix_UB_23      -0.0161575000
_diffrn_orient_matrix_UB_31      -0.0219407000
_diffrn_orient_matrix_UB_32      0.0222386000
_diffrn_orient_matrix_UB_33      0.0122658000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                6381
_reflns_number_total             9663
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         1.643
_refine_diff_density_min         -1.085
_refine_diff_density_rms         0.122
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     414
_refine_ls_number_reflns         9663
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.1118
_refine_ls_R_factor_gt           0.0660
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0388P)²+21.8704P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1368
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
F5 \\sim F6 \\sim F7 \\sim F8 \\sim F9 \\sim F4: within 1.7A with sigma of 0.04
and sigma for terminal atoms of 0.08
Uanis(F4) = Uanis(F5) = Uanis(F6) = Uanis(F7) = Uanis(F8) = Uanis(F9)
3. Others
 Fixed Sof: F6(0.5) F8(0.5) F4(0.5) F9(0.5) F7(0.5) F5(0.5)
4.a Riding coordinates:
 C24(H24)
4.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C2(H2A,H2B)
4.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C4(H4), C6(H6), C12(H12), C7(H7), C22(H22), C11(H11), C15(H15),
 C8(H8), C31(H31), C27(H27), C28(H28), C21(H21), C20(H20), C23(H23)
4.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Br2 Br 0.527143(18) 0.34167(4) 0.299960(17) 0.02480(12) Uani 1 d . . . .
Br1 Br 0.713979(18) 0.00123(4) 0.683499(16) 0.02268(11) Uani 1 d . . . .
Cl2 Cl 0.67001(5) 0.61279(10) 0.68797(4) 0.0309(3) Uani 1 d . . . .
Cl1 Cl 0.39591(5) 1.02274(9) 0.66755(4) 0.0257(2) Uani 1 d . . . .
F3 F 0.50386(13) 0.8132(4) 0.84721(11) 0.0655(11) Uani 1 d . . . .
F1 F 0.44018(16) 0.9224(3) 0.87201(11) 0.0554(9) Uani 1 d . . . .
F2 F 0.43183(13) 0.7358(3) 0.87311(10) 0.0421(7) Uani 1 d . . . .
F6 F 0.6381(4) 0.8991(7) 0.8776(3) 0.0559(8) Uani 0.50 d A 1 . U
F8 F 0.6895(3) 0.7389(7) 0.8784(2) 0.0559(8) Uani 0.50 d A 1 . U
F4 F 0.7262(3) 0.9065(7) 0.8677(2) 0.0559(8) Uani 0.50 d A 1 . U
C10 C 0.2198(2) 0.6500(5) 0.61200(18) 0.0384(12) Uani 1 d . . . .
H10A H 0.1870 0.7058 0.6030 0.058 Uiso 1 calc . . GR .
H10B H 0.2051 0.5775 0.6231 0.058 Uiso 1 calc . . GR .
H10C H 0.2357 0.6349 0.5828 0.058 Uiso 1 calc . . GR .
C5 C 0.3947(2) 0.6941(5) 0.53370(19) 0.0381(12) Uani 1 d . . . .
H5 H 0.4153 0.6224 0.5365 0.046 Uiso 1 calc . . R .
N3 N 0.58777(14) 0.8998(3) 0.72305(12) 0.0183(7) Uani 1 d . . . .
C24 C 0.5732(3) 0.6727(6) 0.5238(2) 0.0628(19) Uani 1 d . . . .
H24 H 0.5352 0.6866 0.5117 0.075 Uiso 1 d . . R .
N4 N 0.56984(14) 0.8198(3) 0.64730(12) 0.0187(7) Uani 1 d . . . .
C4 C 0.3617(2) 0.7235(4) 0.56929(17) 0.0293(10) Uani 1 d . . . .
H4 H 0.3606 0.6719 0.5958 0.035 Uiso 1 calc . . R .
N2 N 0.30208(14) 0.7988(3) 0.64764(13) 0.0205(7) Uani 1 d . . . .
N1 N 0.33161(14) 0.7443(3) 0.72756(12) 0.0184(7) Uani 1 d . . . .
C6 C 0.3968(2) 0.7705(6) 0.49449(18) 0.0421(14) Uani 1 d . . . .
H6 H 0.4185 0.7498 0.4707 0.050 Uiso 1 calc . . R .
C12 C 0.36473(17) 0.7428(4) 0.77711(15) 0.0196(8) Uani 1 d . . . .
H12 H 0.3583 0.6849 0.7997 0.024 Uiso 1 calc . . R .
C7 C 0.3669(2) 0.8777(6) 0.49031(18) 0.0410(13) Uani 1 d . . . .
H7 H 0.3686 0.9296 0.4640 0.049 Uiso 1 calc . . R .
C26 C 0.4984(2) 0.9663(4) 0.59395(16) 0.0295(10) Uani 1 d . . . .
H26A H 0.5208 0.9638 0.5682 0.044 Uiso 1 calc . . GR .
H26B H 0.4855 1.0461 0.5976 0.044 Uiso 1 calc . . GR .
H26C H 0.4635 0.9159 0.5842 0.044 Uiso 1 calc . . GR .
C25 C 0.53747(17) 0.9251(4) 0.64320(16) 0.0219(9) Uani 1 d . . . .
C22 C 0.6599(3) 0.7385(7) 0.4952(2) 0.070(2) Uani 1 d . . . .
H22 H 0.6828 0.7369 0.4710 0.084 Uiso 1 calc . . R .
C11 C 0.28675(18) 0.6661(4) 0.70355(16) 0.0227(9) Uani 1 d . . . .
H11 H 0.2719 0.6024 0.7186 0.027 Uiso 1 calc . . R .
C15 C 0.41725(18) 0.9160(4) 0.75852(16) 0.0219(9) Uani 1 d . . . .
H15 H 0.4464 0.9742 0.7698 0.026 Uiso 1 calc . . R .
C9 C 0.26869(18) 0.6997(4) 0.65420(16) 0.0244(9) Uani 1 d . . . .
C17 C 0.60170(17) 0.8054(4) 0.69592(15) 0.0179(8) Uani 1 d . . . .
C18 C 0.55665(19) 0.7273(4) 0.60772(16) 0.0248(9) Uani 1 d . . . .
H18A H 0.5140 0.7315 0.5903 0.030 Uiso 1 calc . . R .
H18B H 0.5638 0.6506 0.6242 0.030 Uiso 1 calc . . R .
C19 C 0.59345(19) 0.7359(4) 0.56869(15) 0.0256(10) Uani 1 d . . . .
C8 C 0.33419(19) 0.9076(5) 0.52551(16) 0.0308(11) Uani 1 d . . . .
H8 H 0.3144 0.9802 0.5228 0.037 Uiso 1 calc . . R .
C31 C 0.66925(18) 0.7353(4) 0.77252(16) 0.0230(9) Uani 1 d . . . .
H31 H 0.6980 0.6815 0.7897 0.028 Uiso 1 calc . . R .
C13 C 0.40705(17) 0.8277(4) 0.79248(15) 0.0200(8) Uani 1 d . . . .
C27 C 0.54853(17) 0.9744(4) 0.68998(15) 0.0199(8) Uani 1 d . . . .
H27 H 0.5327 1.0454 0.6984 0.024 Uiso 1 calc . . R .
C2 C 0.29082(19) 0.8657(4) 0.59973(15) 0.0234(9) Uani 1 d . . . .
H2A H 0.2969 0.9491 0.6077 0.028 Uiso 1 calc . . R .
H2B H 0.2487 0.8551 0.5816 0.028 Uiso 1 calc . . R .
C1 C 0.34067(17) 0.8268(3) 0.69267(14) 0.0165(8) Uani 1 d . . . .
C28 C 0.61060(17) 0.9127(4) 0.77429(15) 0.0194(8) Uani 1 d . . . .
H28 H 0.5994 0.9765 0.7917 0.023 Uiso 1 calc . . R .
C21 C 0.6798(2) 0.8026(5) 0.53943(18) 0.0354(11) Uani 1 d . . . .
H21 H 0.7155 0.8461 0.5449 0.042 Uiso 1 calc . . R .
C29 C 0.65010(17) 0.8302(4) 0.79916(15) 0.0210(9) Uani 1 d A . . .
C3 C 0.33050(17) 0.8306(4) 0.56487(15) 0.0229(9) Uani 1 d . . . .
C16 C 0.38418(17) 0.9155(4) 0.70911(16) 0.0202(9) Uani 1 d . . . .
C20 C 0.64591(18) 0.8016(4) 0.57580(16) 0.0245(9) Uani 1 d . . . .
H20 H 0.6589 0.8459 0.6055 0.029 Uiso 1 calc . . R .
C30 C 0.6736(2) 0.8410(4) 0.85475(17) 0.0271(10) Uani 1 d . . . .
C32 C 0.64507(18) 0.7239(4) 0.72164(16) 0.0212(9) Uani 1 d . . . .
C23 C 0.6059(4) 0.6762(8) 0.4865(3) 0.092(3) Uani 1 d . . . .
H23 H 0.5915 0.6368 0.4558 0.111 Uiso 1 calc . . R .
C14 C 0.4457(2) 0.8252(4) 0.84590(17) 0.0275(10) Uani 1 d . . . .
F9 F 0.7307(3) 0.8328(7) 0.8713(2) 0.0559(8) Uani 0.50 d A 2 . U
F7 F 0.6454(3) 0.7631(7) 0.8795(2) 0.0559(8) Uani 0.50 d A 2 . U
F5 F 0.6569(4) 0.9451(7) 0.8751(3) 0.0559(8) Uani 0.50 d A 2 . U

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br2 0.0242(2) 0.0216(2) 0.0322(2) 0.00703(19) 0.01387(18) 0.00333(17)
Br1 0.0212(2) 0.0203(2) 0.0282(2) -0.00508(18) 0.00921(16) -0.00238(17)
Cl2 0.0398(6) 0.0249(6) 0.0318(6) -0.0019(5) 0.0157(5) 0.0085(5)
Cl1 0.0286(5) 0.0229(5) 0.0286(6) 0.0073(4) 0.0124(4) 0.0009(4)
F3 0.0250(16) 0.129(4) 0.0375(18) 0.010(2) -0.0019(13) 0.0013(18)
F1 0.093(3) 0.0297(17) 0.0302(16) -0.0086(14) -0.0111(16) 0.0072(16)
F2 0.0598(19) 0.0366(17) 0.0228(14) 0.0079(13) -0.0036(13) -0.0076(14)
F6 0.074(2) 0.065(2) 0.0222(11) -0.0066(16) -0.0009(13) -0.0059(19)
F8 0.074(2) 0.065(2) 0.0222(11) -0.0066(16) -0.0009(13) -0.0059(19)
F4 0.074(2) 0.065(2) 0.0222(11) -0.0066(16) -0.0009(13) -0.0059(19)
C10 0.032(3) 0.044(3) 0.032(3) 0.011(2) -0.004(2) -0.008(2)
C5 0.034(3) 0.044(3) 0.037(3) -0.013(2) 0.009(2) 0.001(2)
N3 0.0190(17) 0.0189(18) 0.0175(17) -0.0013(14) 0.0056(14) -0.0015(13)
C24 0.066(4) 0.084(5) 0.048(4) -0.030(4) 0.031(3) -0.031(4)
N4 0.0196(17) 0.0216(18) 0.0154(17) -0.0026(14) 0.0054(13) -0.0013(14)
C4 0.034(3) 0.029(3) 0.025(2) 0.000(2) 0.006(2) 0.001(2)
N2 0.0192(17) 0.0210(18) 0.0212(18) 0.0058(15) 0.0047(14) 0.0023(14)
N1 0.0154(16) 0.0200(18) 0.0198(18) 0.0031(14) 0.0046(13) 0.0004(13)
C6 0.030(3) 0.073(4) 0.022(3) -0.014(3) 0.006(2) -0.009(3)
C12 0.022(2) 0.018(2) 0.020(2) 0.0041(17) 0.0068(17) 0.0028(16)
C7 0.028(3) 0.070(4) 0.023(2) 0.006(3) 0.002(2) -0.010(3)
C26 0.028(2) 0.039(3) 0.021(2) -0.004(2) 0.0035(18) 0.001(2)
C25 0.017(2) 0.025(2) 0.024(2) -0.0002(18) 0.0054(17) -0.0016(17)
C22 0.084(5) 0.099(6) 0.045(4) -0.031(4) 0.049(3) -0.037(4)
C11 0.022(2) 0.020(2) 0.026(2) 0.0036(18) 0.0054(17) -0.0037(17)
C15 0.022(2) 0.019(2) 0.026(2) -0.0014(18) 0.0094(18) 0.0005(16)
C9 0.022(2) 0.026(2) 0.025(2) 0.0019(19) 0.0042(17) -0.0014(17)
C17 0.0167(19) 0.019(2) 0.020(2) -0.0025(17) 0.0087(16) -0.0055(15)
C18 0.026(2) 0.026(2) 0.024(2) -0.0079(19) 0.0072(18) -0.0069(18)
C19 0.032(2) 0.030(2) 0.017(2) -0.0032(19) 0.0093(18) -0.0022(19)
C8 0.023(2) 0.045(3) 0.022(2) 0.010(2) 0.0016(18) -0.003(2)
C31 0.022(2) 0.023(2) 0.024(2) 0.0058(18) 0.0065(17) 0.0006(17)
C13 0.0196(19) 0.020(2) 0.020(2) 0.0028(17) 0.0059(16) 0.0040(16)
C27 0.0180(19) 0.019(2) 0.022(2) -0.0017(17) 0.0047(16) 0.0005(16)
C2 0.026(2) 0.025(2) 0.018(2) 0.0088(18) 0.0045(17) 0.0041(18)
C1 0.0193(19) 0.0157(19) 0.0170(19) 0.0046(16) 0.0090(16) 0.0066(15)
C28 0.021(2) 0.021(2) 0.017(2) -0.0061(17) 0.0056(16) -0.0030(16)
C21 0.033(3) 0.046(3) 0.030(3) 0.002(2) 0.013(2) -0.006(2)
C29 0.019(2) 0.024(2) 0.020(2) -0.0001(18) 0.0045(16) -0.0046(17)
C3 0.0168(19) 0.031(2) 0.019(2) 0.0016(19) 0.0014(16) -0.0033(17)
C16 0.021(2) 0.017(2) 0.026(2) 0.0065(18) 0.0111(17) 0.0050(16)
C20 0.025(2) 0.028(2) 0.019(2) -0.0022(19) 0.0037(17) -0.0003(18)
C30 0.025(2) 0.029(2) 0.028(2) 0.001(2) 0.0062(18) 0.0035(19)
C32 0.024(2) 0.017(2) 0.026(2) -0.0021(18) 0.0127(18) -0.0003(16)
C23 0.119(6) 0.123(7) 0.055(4) -0.060(5) 0.060(4) -0.068(6)
C14 0.029(2) 0.029(3) 0.025(2) 0.002(2) 0.0070(19) 0.0007(19)
F9 0.074(2) 0.065(2) 0.0222(11) -0.0066(16) -0.0009(13) -0.0059(19)
F7 0.074(2) 0.065(2) 0.0222(11) -0.0066(16) -0.0009(13) -0.0059(19)
F5 0.074(2) 0.065(2) 0.0222(11) -0.0066(16) -0.0009(13) -0.0059(19)

_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
Cl2 C32 1.726(4) . ?
Cl1 C16 1.717(4) . ?
F3 C14 1.321(5) . ?
F1 C14 1.329(5) . ?
F2 C14 1.333(5) . ?
F6 C30 1.305(9) . ?
F8 C30 1.326(8) . ?
F4 C30 1.377(9) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C10 C9 1.495(6) . ?
C5 H5 0.9300 . ?
C5 C4 1.397(6) . ?
C5 C6 1.377(7) . ?
N3 C17 1.374(5) . ?
N3 C27 1.384(5) . ?
N3 C28 1.362(5) . ?
C24 H24 0.8600 . ?
C24 C19 1.385(7) . ?
C24 C23 1.393(8) . ?
N4 C25 1.389(5) . ?
N4 C17 1.346(5) . ?
N4 C18 1.473(5) . ?
C4 H4 0.9300 . ?
C4 C3 1.393(6) . ?
N2 C9 1.388(5) . ?
N2 C2 1.467(5) . ?
N2 C1 1.352(5) . ?
N1 C12 1.366(5) . ?
N1 C11 1.385(5) . ?
N1 C1 1.377(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.381(8) . ?
C12 H12 0.9300 . ?
C12 C13 1.350(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.385(7) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C26 C25 1.483(6) . ?
C25 C27 1.348(6) . ?
C22 H22 0.9300 . ?
C22 C21 1.376(7) . ?
C22 C23 1.383(9) . ?
C11 H11 0.9300 . ?
C11 C9 1.350(6) . ?
C15 H15 0.9300 . ?
C15 C13 1.413(6) . ?
C15 C16 1.362(6) . ?
C17 C32 1.404(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.502(6) . ?
C19 C20 1.378(6) . ?
C8 H8 0.9300 . ?
C8 C3 1.392(6) . ?
C31 H31 0.9300 . ?
C31 C29 1.419(6) . ?
C31 C32 1.356(6) . ?
C13 C14 1.496(6) . ?
C27 H27 0.9300 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.509(6) . ?
C1 C16 1.402(6) . ?
C28 H28 0.9300 . ?
C28 C29 1.354(6) . ?
C21 H21 0.9300 . ?
C21 C20 1.389(6) . ?
C29 C30 1.471(6) . ?
C20 H20 0.9300 . ?
C30 F9 1.270(8) . ?
C30 F7 1.359(8) . ?
C30 F5 1.390(9) . ?
C23 H23 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
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C6 C5 C4 120.4(5) . . ?
C17 N3 C27 108.9(3) . . ?
C28 N3 C17 123.0(4) . . ?
C28 N3 C27 128.0(3) . . ?
C19 C24 H24 109.2 . . ?
C19 C24 C23 119.7(5) . . ?
C23 C24 H24 112.5 . . ?
C25 N4 C18 122.7(3) . . ?
C17 N4 C25 109.2(3) . . ?
C17 N4 C18 126.1(4) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 C5 119.7(4) . . ?
C3 C4 H4 120.1 . . ?
C9 N2 C2 123.1(3) . . ?
C1 N2 C9 109.2(3) . . ?
C1 N2 C2 127.5(3) . . ?
C12 N1 C11 128.1(3) . . ?
C12 N1 C1 122.7(3) . . ?
C1 N1 C11 109.1(3) . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C7 120.2(5) . . ?
C7 C6 H6 119.9 . . ?
N1 C12 H12 120.9 . . ?
C13 C12 N1 118.3(4) . . ?
C13 C12 H12 120.9 . . ?
C6 C7 H7 120.2 . . ?
C6 C7 C8 119.6(5) . . ?
C8 C7 H7 120.2 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
N4 C25 C26 122.0(4) . . ?
C27 C25 N4 107.8(4) . . ?
C27 C25 C26 130.1(4) . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C23 120.3(5) . . ?
C23 C22 H22 119.9 . . ?
N1 C11 H11 126.5 . . ?
C9 C11 N1 107.1(4) . . ?
C9 C11 H11 126.5 . . ?
C13 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C16 C15 C13 119.6(4) . . ?
N2 C9 C10 122.3(4) . . ?
C11 C9 C10 129.6(4) . . ?
C11 C9 N2 108.0(4) . . ?
N3 C17 C32 118.1(4) . . ?
N4 C17 N3 106.7(3) . . ?
N4 C17 C32 135.0(4) . . ?
N4 C18 H18A 108.6 . . ?
N4 C18 H18B 108.6 . . ?
N4 C18 C19 114.5(3) . . ?
H18A C18 H18B 107.6 . . ?
C19 C18 H18A 108.6 . . ?
C19 C18 H18B 108.6 . . ?
C24 C19 C18 117.3(4) . . ?
C20 C19 C24 119.4(4) . . ?
C20 C19 C18 123.3(4) . . ?
C7 C8 H8 119.5 . . ?
C7 C8 C3 121.0(5) . . ?
C3 C8 H8 119.5 . . ?
C29 C31 H31 120.4 . . ?
C32 C31 H31 120.4 . . ?
C32 C31 C29 119.2(4) . . ?
C12 C13 C15 121.3(4) . . ?
C12 C13 C14 119.4(4) . . ?
C15 C13 C14 119.3(4) . . ?
N3 C27 H27 126.4 . . ?
C25 C27 N3 107.2(4) . . ?
C25 C27 H27 126.4 . . ?
N2 C2 H2A 108.6 . . ?
N2 C2 H2B 108.6 . . ?
N2 C2 C3 114.5(3) . . ?
H2A C2 H2B 107.6 . . ?
C3 C2 H2A 108.6 . . ?
C3 C2 H2B 108.6 . . ?
N2 C1 N1 106.5(3) . . ?
N2 C1 C16 134.8(4) . . ?
N1 C1 C16 118.6(3) . . ?
N3 C28 H28 120.9 . . ?
C29 C28 N3 118.2(4) . . ?
C29 C28 H28 120.9 . . ?
C22 C21 H21 120.4 . . ?
C22 C21 C20 119.3(5) . . ?
C20 C21 H21 120.4 . . ?
C31 C29 C30 120.1(4) . . ?
C28 C29 C31 121.2(4) . . ?
C28 C29 C30 118.7(4) . . ?
C4 C3 C2 123.0(4) . . ?
C8 C3 C4 118.9(4) . . ?
C8 C3 C2 118.0(4) . . ?
C15 C16 Cl1 120.1(3) . . ?
C15 C16 C1 119.4(4) . . ?
C1 C16 Cl1 120.5(3) . . ?
C19 C20 C21 121.1(4) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
F6 C30 F8 109.7(5) . . ?
F6 C30 F4 102.1(5) . . ?
F6 C30 C29 114.4(5) . . ?
F6 C30 F7 70.9(5) . . ?
F6 C30 F5 29.3(4) . . ?
F8 C30 F4 103.2(5) . . ?
F8 C30 C29 114.1(4) . . ?
F8 C30 F7 45.9(4) . . ?
F8 C30 F5 127.9(5) . . ?
F4 C30 C29 112.3(4) . . ?
F4 C30 F5 75.5(5) . . ?
F9 C30 F6 124.6(6) . . ?
F9 C30 F8 68.3(5) . . ?
F9 C30 F4 36.8(4) . . ?
F9 C30 C29 116.0(4) . . ?
F9 C30 F7 110.1(6) . . ?
F9 C30 F5 106.1(6) . . ?
F7 C30 F4 135.2(5) . . ?
F7 C30 C29 110.7(4) . . ?
F7 C30 F5 98.4(5) . . ?
F5 C30 C29 114.1(5) . . ?
C17 C32 Cl2 119.9(3) . . ?
C31 C32 Cl2 120.0(3) . . ?
C31 C32 C17 120.0(4) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 C24 120.1(6) . . ?
C22 C23 H23 119.9 . . ?
F3 C14 F1 107.2(4) . . ?
F3 C14 F2 106.2(4) . . ?
F3 C14 C13 112.1(3) . . ?
F1 C14 F2 105.5(4) . . ?
F1 C14 C13 112.8(4) . . ?
F2 C14 C13 112.6(4) . . ?

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
C5 C4 C3 C8 -1.6(7) . . . . ?
C5 C4 C3 C2 176.2(4) . . . . ?
C5 C6 C7 C8 -0.6(7) . . . . ?
N3 C17 C32 Cl2 -173.2(3) . . . . ?
N3 C17 C32 C31 4.0(6) . . . . ?
N3 C28 C29 C31 2.5(6) . . . . ?
N3 C28 C29 C30 -178.1(4) . . . . ?
C24 C19 C20 C21 -1.9(8) . . . . ?
N4 C25 C27 N3 0.0(4) . . . . ?
N4 C17 C32 Cl2 2.5(6) . . . . ?
N4 C17 C32 C31 179.7(4) . . . . ?
N4 C18 C19 C24 -163.8(5) . . . . ?
N4 C18 C19 C20 17.1(6) . . . . ?
C4 C5 C6 C7 0.7(7) . . . . ?
N2 C2 C3 C4 18.4(6) . . . . ?
N2 C2 C3 C8 -163.8(4) . . . . ?
N2 C1 C16 Cl1 1.8(6) . . . . ?
N2 C1 C16 C15 -178.2(4) . . . . ?
N1 C12 C13 C15 -0.1(6) . . . . ?
N1 C12 C13 C14 -177.4(4) . . . . ?
N1 C11 C9 C10 -176.9(4) . . . . ?
N1 C11 C9 N2 -0.2(5) . . . . ?
N1 C1 C16 Cl1 -178.3(3) . . . . ?
N1 C1 C16 C15 1.6(5) . . . . ?
C6 C5 C4 C3 0.4(7) . . . . ?
C6 C7 C8 C3 -0.6(7) . . . . ?
C12 N1 C11 C9 -177.5(4) . . . . ?
C12 N1 C1 N2 177.6(3) . . . . ?
C12 N1 C1 C16 -2.3(5) . . . . ?
C12 C13 C14 F3 118.4(4) . . . . ?
C12 C13 C14 F1 -120.5(4) . . . . ?
C12 C13 C14 F2 -1.2(6) . . . . ?
C7 C8 C3 C4 1.7(7) . . . . ?
C7 C8 C3 C2 -176.1(4) . . . . ?
C26 C25 C27 N3 179.3(4) . . . . ?
C25 N4 C17 N3 2.1(4) . . . . ?
C25 N4 C17 C32 -173.9(4) . . . . ?
C25 N4 C18 C19 93.0(5) . . . . ?
C22 C21 C20 C19 1.1(8) . . . . ?
C11 N1 C12 C13 179.2(4) . . . . ?
C11 N1 C1 N2 -0.5(4) . . . . ?
C11 N1 C1 C16 179.6(3) . . . . ?
C15 C13 C14 F3 -59.0(5) . . . . ?
C15 C13 C14 F1 62.1(5) . . . . ?
C15 C13 C14 F2 -178.7(4) . . . . ?
C9 N2 C2 C3 -95.4(5) . . . . ?
C9 N2 C1 N1 0.4(4) . . . . ?
C9 N2 C1 C16 -179.8(4) . . . . ?
C17 N3 C27 C25 1.3(4) . . . . ?
C17 N3 C28 C29 1.9(5) . . . . ?
C17 N4 C25 C26 179.3(4) . . . . ?
C17 N4 C25 C27 -1.4(4) . . . . ?
C17 N4 C18 C19 -104.9(5) . . . . ?
C18 N4 C25 C26 -16.0(6) . . . . ?
C18 N4 C25 C27 163.3(3) . . . . ?
C18 N4 C17 N3 -161.9(3) . . . . ?
C18 N4 C17 C32 22.0(7) . . . . ?
C18 C19 C20 C21 177.2(4) . . . . ?
C19 C24 C23 C22 2.9(13) . . . . ?
C31 C29 C30 F6 -155.1(5) . . . . ?
C31 C29 C30 F8 -27.7(6) . . . . ?
C31 C29 C30 F4 89.2(6) . . . . ?
C31 C29 C30 F9 48.9(7) . . . . ?
C31 C29 C30 F7 -77.4(6) . . . . ?
C31 C29 C30 F5 172.7(5) . . . . ?
C13 C15 C16 Cl1 179.7(3) . . . . ?
C13 C15 C16 C1 -0.3(6) . . . . ?
C27 N3 C17 N4 -2.1(4) . . . . ?
C27 N3 C17 C32 174.7(3) . . . . ?
C27 N3 C28 C29 -178.0(4) . . . . ?
C2 N2 C9 C10 2.5(6) . . . . ?
C2 N2 C9 C11 -174.5(4) . . . . ?
C2 N2 C1 N1 174.5(3) . . . . ?
C2 N2 C1 C16 -5.7(7) . . . . ?
C1 N2 C9 C10 176.9(4) . . . . ?
C1 N2 C9 C11 -0.1(5) . . . . ?
C1 N2 C2 C3 91.3(5) . . . . ?
C1 N1 C12 C13 1.5(5) . . . . ?
C1 N1 C11 C9 0.4(4) . . . . ?
C28 N3 C17 N4 178.0(3) . . . . ?
C28 N3 C17 C32 -5.1(5) . . . . ?
C28 N3 C27 C25 -178.9(4) . . . . ?
C28 C29 C30 F6 25.4(7) . . . . ?
C28 C29 C30 F8 152.8(5) . . . . ?
C28 C29 C30 F4 -90.3(6) . . . . ?
C28 C29 C30 F9 -130.6(6) . . . . ?
C28 C29 C30 F7 103.1(5) . . . . ?
C28 C29 C30 F5 -6.8(6) . . . . ?
C21 C22 C23 C24 -3.7(13) . . . . ?
C29 C31 C32 Cl2 177.3(3) . . . . ?
C29 C31 C32 C17 0.0(6) . . . . ?
C16 C15 C13 C12 -0.5(6) . . . . ?
C16 C15 C13 C14 176.8(4) . . . . ?
C32 C31 C29 C28 -3.4(6) . . . . ?
C32 C31 C29 C30 177.1(4) . . . . ?
C23 C24 C19 C18 -179.3(7) . . . . ?
C23 C24 C19 C20 -0.1(10) . . . . ?
C23 C22 C21 C20 1.7(11) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
4 2 -37 0.0384 3.5338 2.2383 -37.3895 -0.5205 0.7018 -0.4864
-17 13 6 0.0400 -17.0789 13.4805 5.5375 0.1122 0.6605 0.7424
-2 -3 37 0.0261 -2.4994 -3.0326 36.8946 0.5115 -0.7381 0.4399
18 -12 -17 0.0086 17.5620 -12.2823 -17.0811 -0.2717 -0.4157 -0.8680
4 11 26 0.0346 3.7757 10.7426 25.7940 0.8748 0.1076 0.4724
-24 -1 32 0.0189 -23.6917 -0.6954 31.7583 -0.0000 -0.4483 0.8939
-3 -11 -27 0.0299 -2.7050 -10.5337 -26.7143 -0.8602 -0.0867 -0.5026
22 -1 -33 0.0312 22.0110 -0.6417 -33.2426 -0.1060 0.4121 -0.9050

_olex2_date_sample_data_collection 2015-05-06
_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_mrc213
_database_code_depnum_ccdc_archive 'CCDC 1471656'
_audit_update_record             
;
2016-03-31 deposited with the CCDC.
2016-07-22 downloaded from the CCDC.
;
_audit_creation_date             2015-05-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
'(N-Allyl)-8-chloro-6-trifluoromethyl-2-methylimidazo[1,2-a]pyridinium bromide 3im'
_chemical_formula_moiety         'Br, C12 H11 Cl F3 N2'
_chemical_formula_sum            'C12 H9 Br Cl F3 N2'
_chemical_formula_weight         353.57
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C48 H36 Br4 Cl4 F12 N8'
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'
Br Br -0.2901 2.4595 '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'
F F 0.0171 0.0103 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   11.0563(12)
_cell_length_b                   11.1805(12)
_cell_length_c                   12.0711(12)
_cell_angle_alpha                98.874(9)
_cell_angle_beta                 103.353(9)
_cell_angle_gamma                103.781(9)
_cell_volume                     1375.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2531
_cell_measurement_temperature    120.00(11)
_cell_measurement_theta_max      25.0900
_cell_measurement_theta_min      3.0750
_exptl_absorpt_coefficient_mu    3.204
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.708
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.2673
_exptl_crystal_size_mid          0.1112
_exptl_crystal_size_min          0.0797
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0930
_diffrn_reflns_av_unetI/netI     0.1708
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15553
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         31.21
_diffrn_reflns_theta_min         2.89
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3095
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.862
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -33.00   -6.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       12.9509  -37.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega   30.00   78.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       12.9509   37.0000   90.0000 48

#__ type_ start__ end____ width___ exp.time_
  3 omega   15.00   75.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       12.9509   57.0000  -60.0000 60

#__ type_ start__ end____ width___ exp.time_
  4 omega   -9.00   76.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       12.9509   57.0000   28.0000 85

#__ type_ start__ end____ width___ exp.time_
  5 omega    2.00   81.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       12.9509   57.0000  150.0000 79

#__ type_ start__ end____ width___ exp.time_
  6 omega  -11.00   69.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       12.9509   57.0000 -120.0000 80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0243131000
_diffrn_orient_matrix_UB_12      0.0423816000
_diffrn_orient_matrix_UB_13      -0.0307142000
_diffrn_orient_matrix_UB_21      -0.0494501000
_diffrn_orient_matrix_UB_22      -0.0043436000
_diffrn_orient_matrix_UB_23      0.0288530000
_diffrn_orient_matrix_UB_31      0.0411708000
_diffrn_orient_matrix_UB_32      0.0516897000
_diffrn_orient_matrix_UB_33      0.0453822000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                4341
_reflns_number_total             7696
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         2.021
_refine_diff_density_min         -0.685
_refine_diff_density_rms         0.172
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         7696
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1488
_refine_ls_R_factor_gt           0.0758
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0216P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1508
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C15(H15), C23(H23), C19(H19), C20(H20), C8(H8), C3(H3), C11(H11)
2.c X=CH2 refined with riding coordinates:
 C4(H4A,H4B), C16(H16A,H16B)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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
_atom_site_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Br3 Br 0.0000 0.5000 0.5000 0.0222(2) Uani 1 d . . 2 S T P
Br2 Br 0.0000 0.5000 1.0000 0.0224(2) Uani 1 d . . 2 S T P
Br1 Br -0.26818(6) 0.93742(5) 1.14086(5) 0.02159(16) Uani 1 d . . 1 . . .
Cl2 Cl 0.11223(14) 0.92453(13) 1.14891(12) 0.0248(3) Uani 1 d . . 1 . . .
Cl1 Cl -0.10652(15) 0.88845(14) 1.60625(13) 0.0264(4) Uani 1 d . . 1 . . .
F4 F -0.3192(3) 0.7738(4) 0.7628(4) 0.0457(11) Uani 1 d . . 1 . . .
F5 F -0.3059(3) 0.5917(4) 0.6890(3) 0.0427(11) Uani 1 d . . 1 . . .
F2 F 0.3902(4) 0.9823(3) 1.5599(4) 0.0472(11) Uani 1 d . . 1 . . .
F6 F -0.3367(3) 0.6273(3) 0.8580(3) 0.0332(9) Uani 1 d . . 1 . . .
F3 F 0.3675(4) 0.8249(5) 1.6414(4) 0.0561(13) Uani 1 d . . 1 . . .
F1 F 0.3884(3) 0.8029(4) 1.4670(3) 0.0422(10) Uani 1 d . . 1 . . .
N2 N -0.1998(5) 0.7261(4) 1.3337(4) 0.0206(11) Uani 1 d . . 1 . . .
C6 C -0.3206(6) 0.5976(5) 1.1307(5) 0.0271(15) Uani 1 d . . 1 . . .
H6A H -0.3842 0.5458 1.1589 0.041 Uiso 1 calc . . 1 GR . .
H6B H -0.3018 0.5462 1.0692 0.041 Uiso 1 calc . . 1 GR . .
H6C H -0.3538 0.6619 1.1013 0.041 Uiso 1 calc . . 1 GR . .
N4 N 0.2644(4) 0.8075(4) 0.9753(4) 0.0157(10) Uani 1 d . . 1 . . .
N1 N 0.0007(5) 0.7325(4) 1.3380(4) 0.0206(11) Uani 1 d . . 1 . . .
C4 C -0.3520(6) 0.5328(6) 1.4178(5) 0.0284(15) Uani 1 d . . 1 . . .
H4A H -0.2733 0.5256 1.4067 0.034 Uiso 1 calc . . 1 R . .
H4B H -0.4036 0.4697 1.4425 0.034 Uiso 1 calc . . 1 R . .
N3 N 0.0816(4) 0.7181(4) 0.8376(4) 0.0151(10) Uani 1 d . . 1 . . .
C16 C 0.3349(6) 0.6973(6) 1.1712(5) 0.0290(15) Uani 1 d . . 1 . . .
H16A H 0.2749 0.6459 1.1032 0.035 Uiso 1 calc . . 1 R . .
H16B H 0.3571 0.6642 1.2366 0.035 Uiso 1 calc . . 1 R . .
C18 C 0.4252(5) 0.7422(6) 0.8790(5) 0.0242(14) Uani 1 d . . 1 . . .
H18A H 0.4736 0.8252 0.8776 0.036 Uiso 1 calc . . 1 GR . .
H18B H 0.4229 0.6830 0.8113 0.036 Uiso 1 calc . . 1 GR . .
H18C H 0.4658 0.7184 0.9482 0.036 Uiso 1 calc . . 1 GR . .
C22 C -0.2712(6) 0.6788(6) 0.7880(5) 0.0266(15) Uani 1 d . . 1 . . .
C12 C -0.0168(6) 0.8405(5) 1.5186(5) 0.0183(13) Uani 1 d . . 1 . . .
C17 C 0.2912(5) 0.7420(5) 0.8790(5) 0.0184(13) Uani 1 d . . 1 . . .
C7 C -0.0773(6) 0.6604(5) 1.2298(5) 0.0221(14) Uani 1 d . . 1 . . .
H7 H -0.0500 0.6215 1.1703 0.026 Uiso 1 calc . . 1 R . .
C5 C -0.2001(6) 0.6576(5) 1.2276(5) 0.0218(14) Uani 1 d . . 1 . . .
C9 C 0.1893(5) 0.8264(5) 1.4918(5) 0.0191(13) Uani 1 d . . 1 . . .
C14 C 0.3654(5) 0.8858(5) 1.0801(5) 0.0201(13) Uani 1 d . . 1 . . .
H14A H 0.3400 0.9596 1.1081 0.024 Uiso 1 calc . . 1 R . .
H14B H 0.4455 0.9149 1.0595 0.024 Uiso 1 calc . . 1 R . .
C24 C 0.0515(5) 0.8325(5) 1.0081(5) 0.0176(12) Uani 1 d . . 1 . . .
C15 C 0.3888(5) 0.8177(6) 1.1748(5) 0.0233(14) Uani 1 d . . 1 . . .
H15 H 0.4481 0.8646 1.2450 0.028 Uiso 1 calc . . 1 R . .
C23 C -0.0778(5) 0.7998(5) 0.9560(5) 0.0214(13) Uani 1 d . . 1 . . .
H23 H -0.1326 0.8294 0.9941 0.026 Uiso 1 calc . . 1 R . .
C19 C 0.1790(5) 0.6879(5) 0.7951(5) 0.0166(12) Uani 1 d . . 1 . . .
H19 H 0.1688 0.6391 0.7220 0.020 Uiso 1 calc . . 1 R . .
C20 C -0.0490(5) 0.6802(5) 0.7841(5) 0.0168(12) Uani 1 d . . 1 . . .
H20 H -0.0826 0.6285 0.7095 0.020 Uiso 1 calc . . 1 R . .
C8 C 0.1308(6) 0.7590(5) 1.3813(5) 0.0217(13) Uani 1 d . . 1 . . .
H8 H 0.1797 0.7309 1.3352 0.026 Uiso 1 calc . . 1 R . .
C3 C -0.3903(6) 0.6326(6) 1.3985(5) 0.0304(15) Uani 1 d . . 1 . . .
H3 H -0.4697 0.6350 1.4109 0.036 Uiso 1 calc . . 1 R . .
C13 C 0.1354(5) 0.7924(5) 0.9491(5) 0.0157(12) Uani 1 d . . 1 . . .
C2 C -0.3195(5) 0.7428(6) 1.3585(5) 0.0237(14) Uani 1 d . . 1 . . .
H2A H -0.3761 0.7534 1.2885 0.028 Uiso 1 calc . . 1 R . .
H2B H -0.2982 0.8190 1.4184 0.028 Uiso 1 calc . . 1 R . .
C10 C 0.3335(6) 0.8587(6) 1.5406(6) 0.0318(16) Uani 1 d . . 1 . . .
C21 C -0.1285(5) 0.7201(5) 0.8429(5) 0.0186(12) Uani 1 d . . 1 . . .
C1 C -0.0781(6) 0.7699(5) 1.4029(5) 0.0195(13) Uani 1 d . . 1 . . .
C11 C 0.1153(6) 0.8692(5) 1.5632(5) 0.0219(14) Uani 1 d . . 1 . . .
H11 H 0.1559 0.9160 1.6391 0.026 Uiso 1 calc . . 1 R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br3 0.0267(5) 0.0169(4) 0.0177(4) 0.0014(3) 0.0003(3) 0.0037(3)
Br2 0.0340(5) 0.0161(4) 0.0217(5) 0.0044(3) 0.0150(4) 0.0085(4)
Br1 0.0235(3) 0.0189(3) 0.0204(3) 0.0028(2) 0.0047(2) 0.0047(2)
Cl2 0.0323(9) 0.0245(8) 0.0155(7) -0.0031(6) 0.0060(6) 0.0096(6)
Cl1 0.0343(9) 0.0299(8) 0.0201(8) 0.0026(6) 0.0142(6) 0.0138(7)
F4 0.024(2) 0.050(3) 0.066(3) 0.027(2) 0.004(2) 0.0143(19)
F5 0.021(2) 0.066(3) 0.028(2) -0.0095(19) 0.0035(16) 0.0039(18)
F2 0.028(2) 0.031(2) 0.068(3) -0.005(2) 0.010(2) -0.0042(17)
F6 0.023(2) 0.047(2) 0.029(2) 0.0123(17) 0.0114(16) 0.0035(17)
F3 0.034(2) 0.099(4) 0.043(3) 0.036(3) 0.008(2) 0.022(2)
F1 0.029(2) 0.049(2) 0.046(3) -0.0045(19) 0.0116(18) 0.0148(19)
N2 0.025(3) 0.020(3) 0.018(3) 0.003(2) 0.008(2) 0.006(2)
C6 0.041(4) 0.018(3) 0.021(3) 0.006(2) 0.007(3) 0.006(3)
N4 0.015(2) 0.018(2) 0.011(2) -0.0001(18) 0.0023(18) 0.0018(19)
N1 0.028(3) 0.017(3) 0.021(3) 0.005(2) 0.014(2) 0.006(2)
C4 0.035(4) 0.026(4) 0.027(4) 0.012(3) 0.015(3) 0.004(3)
N3 0.010(2) 0.014(2) 0.016(2) -0.0012(18) 0.0003(18) -0.0004(18)
C16 0.026(4) 0.038(4) 0.024(4) 0.011(3) 0.003(3) 0.013(3)
C18 0.022(3) 0.027(3) 0.024(3) 0.001(3) 0.009(3) 0.009(3)
C22 0.023(3) 0.038(4) 0.017(3) 0.002(3) 0.006(3) 0.009(3)
C12 0.028(3) 0.011(3) 0.017(3) 0.003(2) 0.010(2) 0.006(2)
C17 0.019(3) 0.019(3) 0.017(3) 0.002(2) 0.007(2) 0.004(2)
C7 0.036(4) 0.018(3) 0.013(3) 0.000(2) 0.009(3) 0.009(3)
C5 0.038(4) 0.018(3) 0.008(3) 0.000(2) 0.007(3) 0.005(3)
C9 0.022(3) 0.014(3) 0.025(3) 0.008(2) 0.010(3) 0.006(2)
C14 0.017(3) 0.017(3) 0.021(3) -0.002(2) -0.001(2) 0.005(2)
C24 0.022(3) 0.015(3) 0.015(3) 0.002(2) 0.007(2) 0.004(2)
C15 0.020(3) 0.030(4) 0.014(3) -0.002(2) -0.001(2) 0.005(3)
C23 0.022(3) 0.014(3) 0.036(4) 0.010(2) 0.016(3) 0.010(2)
C19 0.018(3) 0.015(3) 0.019(3) 0.005(2) 0.010(2) 0.004(2)
C20 0.016(3) 0.016(3) 0.017(3) 0.005(2) 0.003(2) 0.005(2)
C8 0.024(3) 0.021(3) 0.028(3) 0.011(2) 0.015(3) 0.008(3)
C3 0.026(4) 0.041(4) 0.032(4) 0.016(3) 0.016(3) 0.013(3)
C13 0.018(3) 0.010(3) 0.017(3) 0.002(2) 0.005(2) 0.000(2)
C2 0.021(3) 0.031(4) 0.021(3) 0.004(3) 0.005(3) 0.014(3)
C10 0.034(4) 0.030(4) 0.038(4) 0.010(3) 0.017(3) 0.013(3)
C21 0.020(3) 0.022(3) 0.017(3) 0.007(2) 0.006(2) 0.011(2)
C1 0.024(3) 0.016(3) 0.020(3) 0.003(2) 0.010(3) 0.007(2)
C11 0.033(4) 0.017(3) 0.011(3) -0.001(2) 0.004(3) 0.002(3)

_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
Cl2 C24 1.733(5) . ?
Cl1 C12 1.719(6) . ?
F4 C22 1.339(7) . ?
F5 C22 1.332(6) . ?
F2 C10 1.333(7) . ?
F6 C22 1.343(7) . ?
F3 C10 1.327(7) . ?
F1 C10 1.344(7) . ?
N2 C5 1.385(7) . ?
N2 C2 1.469(7) . ?
N2 C1 1.337(7) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C6 C5 1.485(8) . ?
N4 C17 1.406(7) . ?
N4 C14 1.467(6) . ?
N4 C13 1.350(7) . ?
N1 C7 1.387(7) . ?
N1 C8 1.354(7) . ?
N1 C1 1.391(7) . ?
C4 H4A 0.9300 . ?
C4 H4B 0.9300 . ?
C4 C3 1.318(9) . ?
N3 C19 1.384(6) . ?
N3 C20 1.369(6) . ?
N3 C13 1.380(6) . ?
C16 H16A 0.9300 . ?
C16 H16B 0.9300 . ?
C16 C15 1.325(8) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C18 C17 1.481(7) . ?
C22 C21 1.490(8) . ?
C12 C1 1.415(7) . ?
C12 C11 1.373(8) . ?
C17 C19 1.343(7) . ?
C7 H7 0.9300 . ?
C7 C5 1.345(8) . ?
C9 C8 1.351(8) . ?
C9 C10 1.499(8) . ?
C9 C11 1.424(8) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.477(8) . ?
C24 C23 1.356(8) . ?
C24 C13 1.405(7) . ?
C15 H15 0.9300 . ?
C23 H23 0.9300 . ?
C23 C21 1.417(8) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C20 C21 1.361(7) . ?
C8 H8 0.9300 . ?
C3 H3 0.9300 . ?
C3 C2 1.504(8) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C11 H11 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
C5 N2 C2 122.1(5) . . ?
C1 N2 C5 109.2(5) . . ?
C1 N2 C2 128.7(5) . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
C17 N4 C14 123.4(5) . . ?
C13 N4 C17 108.3(4) . . ?
C13 N4 C14 128.2(4) . . ?
C7 N1 C1 108.5(5) . . ?
C8 N1 C7 128.2(5) . . ?
C8 N1 C1 123.1(5) . . ?
H4A C4 H4B 120.0 . . ?
C3 C4 H4A 120.0 . . ?
C3 C4 H4B 120.0 . . ?
C20 N3 C19 128.0(5) . . ?
C20 N3 C13 122.9(5) . . ?
C13 N3 C19 109.0(4) . . ?
H16A C16 H16B 120.0 . . ?
C15 C16 H16A 120.0 . . ?
C15 C16 H16B 120.0 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
F4 C22 F6 105.7(5) . . ?
F4 C22 C21 113.2(5) . . ?
F5 C22 F4 106.9(5) . . ?
F5 C22 F6 106.1(5) . . ?
F5 C22 C21 112.5(5) . . ?
F6 C22 C21 112.0(5) . . ?
C1 C12 Cl1 120.6(4) . . ?
C11 C12 Cl1 119.1(4) . . ?
C11 C12 C1 120.3(5) . . ?
N4 C17 C18 121.7(5) . . ?
C19 C17 N4 108.3(5) . . ?
C19 C17 C18 130.0(5) . . ?
N1 C7 H7 126.6 . . ?
C5 C7 N1 106.8(5) . . ?
C5 C7 H7 126.6 . . ?
N2 C5 C6 122.6(6) . . ?
C7 C5 N2 108.6(5) . . ?
C7 C5 C6 128.8(5) . . ?
C8 C9 C10 120.4(5) . . ?
C8 C9 C11 120.6(5) . . ?
C11 C9 C10 119.0(5) . . ?
N4 C14 H14A 109.0 . . ?
N4 C14 H14B 109.0 . . ?
N4 C14 C15 112.8(5) . . ?
H14A C14 H14B 107.8 . . ?
C15 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
C23 C24 Cl2 119.0(4) . . ?
C23 C24 C13 120.7(5) . . ?
C13 C24 Cl2 120.3(4) . . ?
C16 C15 C14 127.4(5) . . ?
C16 C15 H15 116.3 . . ?
C14 C15 H15 116.3 . . ?
C24 C23 H23 120.4 . . ?
C24 C23 C21 119.2(5) . . ?
C21 C23 H23 120.4 . . ?
N3 C19 H19 126.4 . . ?
C17 C19 N3 107.3(5) . . ?
C17 C19 H19 126.4 . . ?
N3 C20 H20 120.9 . . ?
C21 C20 N3 118.3(5) . . ?
C21 C20 H20 120.9 . . ?
N1 C8 H8 120.2 . . ?
C9 C8 N1 119.6(5) . . ?
C9 C8 H8 120.2 . . ?
C4 C3 H3 116.5 . . ?
C4 C3 C2 127.0(6) . . ?
C2 C3 H3 116.5 . . ?
N4 C13 N3 107.1(4) . . ?
N4 C13 C24 135.1(5) . . ?
N3 C13 C24 117.8(5) . . ?
N2 C2 C3 112.4(5) . . ?
N2 C2 H2A 109.1 . . ?
N2 C2 H2B 109.1 . . ?
C3 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
H2A C2 H2B 107.9 . . ?
F2 C10 F1 105.8(5) . . ?
F2 C10 C9 111.9(5) . . ?
F3 C10 F2 106.8(6) . . ?
F3 C10 F1 107.4(6) . . ?
F3 C10 C9 112.4(5) . . ?
F1 C10 C9 112.0(5) . . ?
C23 C21 C22 119.3(5) . . ?
C20 C21 C22 119.6(5) . . ?
C20 C21 C23 121.1(5) . . ?
N2 C1 N1 106.7(5) . . ?
N2 C1 C12 136.0(5) . . ?
N1 C1 C12 117.3(5) . . ?
C12 C11 C9 119.1(5) . . ?
C12 C11 H11 120.4 . . ?
C9 C11 H11 120.4 . . ?

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
Cl2 C24 C23 C21 -177.3(4) . . . . ?
Cl2 C24 C13 N4 0.3(10) . . . . ?
Cl2 C24 C13 N3 179.3(4) . . . . ?
Cl1 C12 C1 N2 1.1(10) . . . . ?
Cl1 C12 C1 N1 -178.8(4) . . . . ?
Cl1 C12 C11 C9 178.2(4) . . . . ?
F4 C22 C21 C23 67.0(7) . . . . ?
F4 C22 C21 C20 -113.4(6) . . . . ?
F5 C22 C21 C23 -171.8(5) . . . . ?
F5 C22 C21 C20 7.9(8) . . . . ?
F6 C22 C21 C23 -52.4(7) . . . . ?
F6 C22 C21 C20 127.2(6) . . . . ?
N4 C17 C19 N3 -0.2(6) . . . . ?
N4 C14 C15 C16 3.9(9) . . . . ?
N1 C7 C5 N2 -0.6(6) . . . . ?
N1 C7 C5 C6 177.4(6) . . . . ?
C4 C3 C2 N2 3.9(9) . . . . ?
N3 C20 C21 C22 -179.0(5) . . . . ?
N3 C20 C21 C23 0.6(8) . . . . ?
C18 C17 C19 N3 -178.7(6) . . . . ?
C17 N4 C14 C15 -96.1(6) . . . . ?
C17 N4 C13 N3 0.1(6) . . . . ?
C17 N4 C13 C24 179.2(6) . . . . ?
C7 N1 C8 C9 -176.7(6) . . . . ?
C7 N1 C1 N2 -2.5(6) . . . . ?
C7 N1 C1 C12 177.4(5) . . . . ?
C5 N2 C2 C3 83.3(7) . . . . ?
C5 N2 C1 N1 2.2(6) . . . . ?
C5 N2 C1 C12 -177.8(7) . . . . ?
C14 N4 C17 C18 3.3(8) . . . . ?
C14 N4 C17 C19 -175.4(5) . . . . ?
C14 N4 C13 N3 175.2(5) . . . . ?
C14 N4 C13 C24 -5.7(10) . . . . ?
C24 C23 C21 C22 177.0(5) . . . . ?
C24 C23 C21 C20 -2.7(9) . . . . ?
C23 C24 C13 N4 -179.7(6) . . . . ?
C23 C24 C13 N3 -0.7(8) . . . . ?
C19 N3 C20 C21 179.1(5) . . . . ?
C19 N3 C13 N4 -0.2(6) . . . . ?
C19 N3 C13 C24 -179.5(5) . . . . ?
C20 N3 C19 C17 -177.6(5) . . . . ?
C20 N3 C13 N4 177.8(5) . . . . ?
C20 N3 C13 C24 -1.5(8) . . . . ?
C8 N1 C7 C5 178.1(5) . . . . ?
C8 N1 C1 N2 -179.0(5) . . . . ?
C8 N1 C1 C12 1.0(8) . . . . ?
C8 C9 C10 F2 112.5(6) . . . . ?
C8 C9 C10 F3 -127.2(6) . . . . ?
C8 C9 C10 F1 -6.1(8) . . . . ?
C8 C9 C11 C12 0.3(9) . . . . ?
C13 N4 C17 C18 178.7(5) . . . . ?
C13 N4 C17 C19 0.1(6) . . . . ?
C13 N4 C14 C15 89.4(7) . . . . ?
C13 N3 C19 C17 0.3(6) . . . . ?
C13 N3 C20 C21 1.5(8) . . . . ?
C13 C24 C23 C21 2.7(8) . . . . ?
C2 N2 C5 C6 0.9(9) . . . . ?
C2 N2 C5 C7 179.1(5) . . . . ?
C2 N2 C1 N1 -177.9(5) . . . . ?
C2 N2 C1 C12 2.1(11) . . . . ?
C10 C9 C8 N1 -178.9(5) . . . . ?
C10 C9 C11 C12 179.6(5) . . . . ?
C1 N2 C5 C6 -179.2(5) . . . . ?
C1 N2 C5 C7 -1.0(7) . . . . ?
C1 N2 C2 C3 -96.5(7) . . . . ?
C1 N1 C7 C5 1.9(6) . . . . ?
C1 N1 C8 C9 -1.0(8) . . . . ?
C1 C12 C11 C9 -0.4(8) . . . . ?
C11 C12 C1 N2 179.7(6) . . . . ?
C11 C12 C1 N1 -0.3(8) . . . . ?
C11 C9 C8 N1 0.3(8) . . . . ?
C11 C9 C10 F2 -66.7(7) . . . . ?
C11 C9 C10 F3 53.5(8) . . . . ?
C11 C9 C10 F1 174.6(5) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-4 16 -3 0.0559 -4.3156 15.7500 -2.5106 0.8495 0.0726 0.5225
12 3 4 0.0279 12.3444 2.5378 3.5308 -0.3010 -0.5196 0.7996
6 -16 3 0.0352 5.9644 -15.5410 2.9921 -0.8956 -0.1411 -0.4220
-13 -1 -4 0.0650 -12.8623 -1.0030 -3.8048 0.3871 0.5306 -0.7541
7 -13 -8 0.0722 7.3955 -12.5595 -7.8156 -0.4720 -0.5367 -0.6994
10 -9 9 0.0374 9.9210 -9.1720 9.3180 -0.9161 -0.1819 0.3572
-9 14 4 0.0282 -9.2586 13.6551 4.4489 0.6672 0.5269 0.5265
-8 6 -12 0.0384 -8.1331 5.8153 -12.0338 0.8138 0.0297 -0.5804

_olex2_date_sample_data_collection 2015-05-06
_olex2_submission_special_instructions 'No special instructions were received'
