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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2py4br
_database_code_depnum_ccdc_archive 'CCDC 1544813'
_audit_update_record             
;
2017-04-18 deposited with the CCDC.
2018-03-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
(Z)-3-(4-bromophenyl)-2-(pyridin-2-yl)acrylonitrile
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H9 Br N2'
_chemical_formula_sum            'C14 H9 Br N2'
_chemical_formula_weight         285.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   14.4059(4)
_cell_length_b                   3.87086(10)
_cell_length_c                   21.1990(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.308(3)
_cell_angle_gamma                90
_cell_volume                     1145.46(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    4708
_cell_measurement_theta_min      4.24
_cell_measurement_theta_max      71.95

_exptl_crystal_description       lath
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    4.683
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.175
_exptl_absorpt_correction_T_max  0.813
_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_special_details           
;
 ?
;
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            6851
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.359
_diffrn_reflns_theta_max         71.898
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2248
_reflns_number_gt                2055
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0297P)²+0.5583P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2248
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0243
_refine_ls_R_factor_gt           0.0217
_refine_ls_wR_factor_ref         0.0586
_refine_ls_wR_factor_gt          0.0567
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.04222(2) 0.75912(5) 0.25516(2) 0.02479(8) Uani 1 1 d . . . . .
N1 N 0.20307(10) 0.0143(4) -0.10211(7) 0.0198(3) Uani 1 1 d . . . . .
N2 N 0.42073(11) 0.5065(5) 0.08198(8) 0.0324(4) Uani 1 1 d . . . . .
C1 C 0.28088(11) 0.1432(4) -0.05966(7) 0.0166(3) Uani 1 1 d . . . . .
C3 C 0.21518(12) -0.1072(5) -0.15834(8) 0.0222(4) Uani 1 1 d . . . . .
H3 H 0.1609 -0.1999 -0.1886 0.027 Uiso 1 1 calc R U . . .
C4 C 0.30214(12) -0.1071(5) -0.17556(8) 0.0214(4) Uani 1 1 d . . . . .
H4 H 0.3070 -0.1965 -0.2164 0.026 Uiso 1 1 calc R U . . .
C5 C 0.38132(12) 0.0262(5) -0.13193(8) 0.0238(4) Uani 1 1 d . . . . .
H5 H 0.4419 0.0318 -0.1422 0.029 Uiso 1 1 calc R U . . .
C6 C 0.37092(12) 0.1515(5) -0.07301(8) 0.0206(3) Uani 1 1 d . . . . .
H6 H 0.4245 0.2424 -0.0419 0.025 Uiso 1 1 calc R U . . .
C7 C 0.26631(12) 0.2814(4) 0.00272(8) 0.0165(3) Uani 1 1 d . . . . .
C8 C 0.17963(12) 0.2904(4) 0.01658(8) 0.0166(3) Uani 1 1 d . . . . .
H8 H 0.1287 0.1996 -0.0166 0.020 Uiso 1 1 calc R U . . .
C9 C 0.15127(11) 0.4159(4) 0.07386(8) 0.0160(3) Uani 1 1 d . . . . .
C10 C 0.05666(11) 0.3512(5) 0.07722(8) 0.0173(3) Uani 1 1 d . . . . .
H10 H 0.0146 0.2347 0.0421 0.021 Uiso 1 1 calc R U . . .
C11 C 0.02260(12) 0.4513(4) 0.13003(8) 0.0189(3) Uani 1 1 d . . . . .
H11 H -0.0417 0.4043 0.1312 0.023 Uiso 1 1 calc R U . . .
C12 C 0.08388(12) 0.6211(4) 0.18107(8) 0.0183(3) Uani 1 1 d . . . . .
C13 C 0.17774(12) 0.6947(4) 0.17932(8) 0.0193(3) Uani 1 1 d . . . . .
H13 H 0.2189 0.8139 0.2145 0.023 Uiso 1 1 calc R U . . .
C14 C 0.21085(11) 0.5939(5) 0.12625(8) 0.0184(3) Uani 1 1 d . . . . .
H14 H 0.2749 0.6459 0.1252 0.022 Uiso 1 1 calc R U . . .
C15 C 0.35158(12) 0.4082(5) 0.04760(8) 0.0211(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C12 1.8917(16) . ?
N1 C3 1.333(2) . ?
N1 C1 1.348(2) . ?
N2 C15 1.144(2) . ?
C1 C6 1.395(2) . ?
C1 C7 1.489(2) . ?
C3 C4 1.389(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.379(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.352(2) . ?
C7 C15 1.441(2) . ?
C8 C9 1.457(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.405(2) . ?
C9 C14 1.405(2) . ?
C10 C11 1.384(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.382(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.391(2) . ?
C13 C14 1.382(2) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?

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
C3 N1 C1 117.18(14) . . ?
N1 C1 C6 122.33(15) . . ?
N1 C1 C7 116.71(14) . . ?
C6 C1 C7 120.96(15) . . ?
N1 C3 C4 124.13(16) . . ?
N1 C3 H3 117.9 . . ?
C4 C3 H3 117.9 . . ?
C5 C4 C3 118.31(16) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C4 C5 C6 118.75(16) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C5 C6 C1 119.30(16) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
C8 C7 C15 122.01(15) . . ?
C8 C7 C1 122.87(15) . . ?
C15 C7 C1 115.12(15) . . ?
C7 C8 C9 130.84(15) . . ?
C7 C8 H8 114.6 . . ?
C9 C8 H8 114.6 . . ?
C10 C9 C14 117.27(15) . . ?
C10 C9 C8 117.28(15) . . ?
C14 C9 C8 125.45(14) . . ?
C11 C10 C9 122.24(15) . . ?
C11 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?
C12 C11 C10 118.75(15) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C11 C12 C13 120.89(15) . . ?
C11 C12 Br1 120.80(12) . . ?
C13 C12 Br1 118.31(13) . . ?
C14 C13 C12 119.81(16) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C9 121.03(15) . . ?
C13 C14 H14 119.5 . . ?
C9 C14 H14 119.5 . . ?
N2 C15 C7 178.06(18) . . ?

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
C3 N1 C1 C6 0.0(3) . . . . ?
C3 N1 C1 C7 179.41(15) . . . . ?
C1 N1 C3 C4 -0.3(3) . . . . ?
N1 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C4 C5 C6 C1 -0.7(3) . . . . ?
N1 C1 C6 C5 0.5(3) . . . . ?
C7 C1 C6 C5 -178.88(16) . . . . ?
N1 C1 C7 C8 -2.0(2) . . . . ?
C6 C1 C7 C8 177.41(16) . . . . ?
N1 C1 C7 C15 178.35(15) . . . . ?
C6 C1 C7 C15 -2.2(2) . . . . ?
C15 C7 C8 C9 0.1(3) . . . . ?
C1 C7 C8 C9 -179.55(16) . . . . ?
C7 C8 C9 C10 -172.37(17) . . . . ?
C7 C8 C9 C14 7.1(3) . . . . ?
C14 C9 C10 C11 -1.1(3) . . . . ?
C8 C9 C10 C11 178.46(15) . . . . ?
C9 C10 C11 C12 0.1(3) . . . . ?
C10 C11 C12 C13 0.8(3) . . . . ?
C10 C11 C12 Br1 -179.13(13) . . . . ?
C11 C12 C13 C14 -0.7(3) . . . . ?
Br1 C12 C13 C14 179.25(13) . . . . ?
C12 C13 C14 C9 -0.3(3) . . . . ?
C10 C9 C14 C13 1.2(2) . . . . ?
C8 C9 C14 C13 -178.30(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6 N2 0.95 2.83 3.469(2) 125.3 .
C14 H14 N2 0.95 2.55 3.397(2) 148.8 .
C11 H11 N1 0.95 2.78 3.635(2) 151.0 3
C5 H5 N2 0.95 2.74 3.321(2) 120.5 3_665
C5 H5 N2 0.95 2.94 3.466(2) 116.3 3_655

_refine_diff_density_max         0.288
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.055

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CHCL3:HEXANE '
_exptl_crystal_preparation       ', Luminescent'
####################################################################### 
# 
# 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_3py4h
_database_code_depnum_ccdc_archive 'CCDC 1544820'
_audit_update_record             
;
2017-04-18 deposited with the CCDC.
2018-03-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H10 N2'
_chemical_formula_sum            'C14 H10 N2'
_chemical_formula_weight         206.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.3502(4)
_cell_length_b                   4.57161(14)
_cell_length_c                   22.7222(12)
_cell_angle_alpha                90
_cell_angle_beta                 100.633(4)
_cell_angle_gamma                90
_cell_volume                     1056.69(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    2699
_cell_measurement_theta_min      1.82
_cell_measurement_theta_max      25.13

_exptl_crystal_description       lath
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
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_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Goniometer KM4/Xcalibur, detector: Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.989
_diffrn_reflns_number            7880
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.348
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             1872
_reflns_number_gt                1493
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0449P)²+0.1826P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1872
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0886
_refine_ls_wR_factor_gt          0.0821
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.09845(10) 0.3874(2) 0.19820(5) 0.0245(3) Uani 1 1 d . . . . .
N2 N 0.22581(12) 1.0627(3) -0.00181(5) 0.0391(3) Uani 1 1 d . . . . .
C1 C 0.17087(12) 0.7010(2) 0.12505(5) 0.0192(3) Uani 1 1 d . . . . .
C2 C 0.18373(12) 0.5765(3) 0.18200(6) 0.0219(3) Uani 1 1 d . . . . .
H2 H 0.2581 0.6300 0.2111 0.026 Uiso 1 1 calc R U . . .
C4 C -0.00509(13) 0.3124(3) 0.15647(6) 0.0255(3) Uani 1 1 d . . . . .
H4 H -0.0665 0.1768 0.1670 0.031 Uiso 1 1 calc R U . . .
C5 C -0.02723(13) 0.4216(3) 0.09903(6) 0.0270(3) Uani 1 1 d . . . . .
H5 H -0.1022 0.3629 0.0708 0.032 Uiso 1 1 calc R U . . .
C6 C 0.06163(13) 0.6180(3) 0.08326(6) 0.0245(3) Uani 1 1 d . . . . .
H6 H 0.0481 0.6964 0.0439 0.029 Uiso 1 1 calc R U . . .
C7 C 0.26886(12) 0.9124(3) 0.11004(5) 0.0203(3) Uani 1 1 d . . . . .
C8 C 0.36725(12) 1.0277(3) 0.15052(6) 0.0219(3) Uani 1 1 d . . . . .
H8 H 0.3704 0.9621 0.1904 0.026 Uiso 1 1 calc R U . . .
C9 C 0.46984(12) 1.2367(3) 0.14327(6) 0.0223(3) Uani 1 1 d . . . . .
C10 C 0.53454(12) 1.3783(3) 0.19493(6) 0.0266(3) Uani 1 1 d . . . . .
H10 H 0.5107 1.3349 0.2324 0.032 Uiso 1 1 calc R U . . .
C11 C 0.63285(13) 1.5807(3) 0.19235(7) 0.0313(4) Uani 1 1 d . . . . .
H11 H 0.6752 1.6767 0.2278 0.038 Uiso 1 1 calc R U . . .
C12 C 0.66923(13) 1.6429(3) 0.13821(7) 0.0340(4) Uani 1 1 d . . . . .
H12 H 0.7360 1.7832 0.1363 0.041 Uiso 1 1 calc R U . . .
C13 C 0.60832(13) 1.5007(3) 0.08686(7) 0.0336(4) Uani 1 1 d . . . . .
H13 H 0.6345 1.5414 0.0498 0.040 Uiso 1 1 calc R U . . .
C14 C 0.50964(13) 1.2998(3) 0.08912(6) 0.0284(3) Uani 1 1 d . . . . .
H14 H 0.4684 1.2035 0.0535 0.034 Uiso 1 1 calc R U . . .
C15 C 0.24819(13) 0.9984(3) 0.04798(6) 0.0268(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.3348(16) . ?
N1 C4 1.3379(16) . ?
N2 C15 1.1503(17) . ?
C1 C6 1.3886(18) . ?
C1 C2 1.3972(17) . ?
C1 C7 1.4854(17) . ?
C2 H2 0.9500 . ?
C4 C5 1.3766(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.3792(18) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.3473(18) . ?
C7 C15 1.4414(18) . ?
C8 C9 1.4601(17) . ?
C8 H8 0.9500 . ?
C9 C14 1.3979(18) . ?
C9 C10 1.3982(18) . ?
C10 C11 1.3846(19) . ?
C10 H10 0.9500 . ?
C11 C12 1.381(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.382(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.3815(18) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C4 117.03(11) . . ?
C6 C1 C2 116.64(11) . . ?
C6 C1 C7 121.67(11) . . ?
C2 C1 C7 121.69(11) . . ?
N1 C2 C1 124.36(12) . . ?
N1 C2 H2 117.8 . . ?
C1 C2 H2 117.8 . . ?
N1 C4 C5 123.39(12) . . ?
N1 C4 H4 118.3 . . ?
C5 C4 H4 118.3 . . ?
C4 C5 C6 118.70(12) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C5 C6 C1 119.87(12) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
C8 C7 C15 121.20(12) . . ?
C8 C7 C1 124.06(11) . . ?
C15 C7 C1 114.69(11) . . ?
C7 C8 C9 130.77(12) . . ?
C7 C8 H8 114.6 . . ?
C9 C8 H8 114.6 . . ?
C14 C9 C10 118.05(12) . . ?
C14 C9 C8 124.94(12) . . ?
C10 C9 C8 116.99(11) . . ?
C11 C10 C9 121.04(13) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C12 C11 C10 119.91(13) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 119.89(13) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C14 C13 C12 120.44(13) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C9 120.64(13) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?
N2 C15 C7 176.85(14) . . ?

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
C4 N1 C2 C1 0.61(18) . . . . ?
C6 C1 C2 N1 -0.31(18) . . . . ?
C7 C1 C2 N1 179.46(11) . . . . ?
C2 N1 C4 C5 -0.54(18) . . . . ?
N1 C4 C5 C6 0.2(2) . . . . ?
C4 C5 C6 C1 0.13(19) . . . . ?
C2 C1 C6 C5 -0.07(18) . . . . ?
C7 C1 C6 C5 -179.85(11) . . . . ?
C6 C1 C7 C8 171.47(12) . . . . ?
C2 C1 C7 C8 -8.30(18) . . . . ?
C6 C1 C7 C15 -5.97(17) . . . . ?
C2 C1 C7 C15 174.26(11) . . . . ?
C15 C7 C8 C9 -2.3(2) . . . . ?
C1 C7 C8 C9 -179.55(11) . . . . ?
C7 C8 C9 C14 -19.4(2) . . . . ?
C7 C8 C9 C10 162.15(13) . . . . ?
C14 C9 C10 C11 1.63(19) . . . . ?
C8 C9 C10 C11 -179.78(11) . . . . ?
C9 C10 C11 C12 -0.7(2) . . . . ?
C10 C11 C12 C13 -0.7(2) . . . . ?
C11 C12 C13 C14 1.0(2) . . . . ?
C12 C13 C14 C9 -0.1(2) . . . . ?
C10 C9 C14 C13 -1.25(19) . . . . ?
C8 C9 C14 C13 -179.71(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6 N2 0.95 2.82 3.4595(17) 125.3 .
C14 H14 N2 0.95 2.67 3.4400(18) 138.4 .
C2 H2 N1 0.95 2.59 3.4998(17) 160.6 2
C8 H8 N1 0.95 2.51 3.4501(17) 168.2 2
C5 H5 N2 0.95 2.67 3.5116(18) 147.7 3_565
C13 H13 N2 0.95 2.67 3.4484(18) 139.4 3_685
C5 H5 N2 0.95 3.20 3.6038(19) 107.5 3_575

_refine_diff_density_max         0.144
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.040

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_3py4f
_database_code_depnum_ccdc_archive 'CCDC 1544821'
_audit_update_record             
;
2017-04-18 deposited with the CCDC.
2018-03-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H9 F N2'
_chemical_formula_sum            'C14 H9 F N2'
_chemical_formula_weight         224.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   3.76509(10)
_cell_length_b                   47.3024(12)
_cell_length_c                   5.91017(16)
_cell_angle_alpha                90
_cell_angle_beta                 91.941(3)
_cell_angle_gamma                90
_cell_volume                     1051.98(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    4686
_cell_measurement_theta_min      3.73
_cell_measurement_theta_max      72.15

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.802
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.882
_exptl_absorpt_correction_T_max  0.982
_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_special_details           
;
 ?
;

_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            8033
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_av_R_equivalents  0.0225

_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -56
_diffrn_reflns_limit_k_max       47
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.738
_diffrn_reflns_theta_max         67.997
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             1894
_reflns_number_gt                1796
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0528P)²+1.0868P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1894
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0550
_refine_ls_wR_factor_ref         0.1430
_refine_ls_wR_factor_gt          0.1415
_refine_ls_goodness_of_fit_ref   1.228
_refine_ls_restrained_S_all      1.228
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.7787(4) 0.00536(3) 0.7275(2) 0.0341(4) Uani 1 1 d . . . . .
N1 N 1.1696(6) 0.21795(4) 0.3870(3) 0.0298(5) Uani 1 1 d . . . . .
N2 N 0.6280(5) 0.13248(4) 0.1443(3) 0.0253(5) Uani 1 1 d . . . . .
C1 C 1.0961(6) 0.17153(4) 0.5521(4) 0.0195(5) Uani 1 1 d . . . . .
C2 C 1.0652(6) 0.19106(5) 0.3754(4) 0.0244(5) Uani 1 1 d . . . . .
H2 H 0.9617 0.1847 0.2358 0.029 Uiso 1 1 calc R U . . .
C4 C 1.3096(7) 0.22680(5) 0.5859(4) 0.0279(5) Uani 1 1 d . . . . .
H4 H 1.3875 0.2459 0.5984 0.034 Uiso 1 1 calc R U . . .
C5 C 1.3462(6) 0.20947(5) 0.7746(4) 0.0255(5) Uani 1 1 d . . . . .
H5 H 1.4415 0.2167 0.9138 0.031 Uiso 1 1 calc R U . . .
C6 C 1.2424(6) 0.18162(5) 0.7569(4) 0.0213(5) Uani 1 1 d . . . . .
H6 H 1.2701 0.1693 0.8834 0.026 Uiso 1 1 calc R U . . .
C7 C 0.9815(6) 0.14183(4) 0.5194(4) 0.0187(5) Uani 1 1 d . . . . .
C8 C 1.0567(6) 0.12102(5) 0.6713(4) 0.0196(5) Uani 1 1 d . . . . .
H8 H 1.1873 0.1272 0.8025 0.024 Uiso 1 1 calc R U . . .
C9 C 0.9740(5) 0.09087(4) 0.6707(4) 0.0190(5) Uani 1 1 d . . . . .
C10 C 1.0720(6) 0.07590(5) 0.8684(4) 0.0214(5) Uani 1 1 d . . . . .
H10 H 1.1845 0.0857 0.9912 0.026 Uiso 1 1 calc R U . . .
C11 C 1.0094(6) 0.04724(5) 0.8892(4) 0.0251(5) Uani 1 1 d . . . . .
H11 H 1.0779 0.0374 1.0237 0.030 Uiso 1 1 calc R U . . .
C12 C 0.8445(6) 0.03337(5) 0.7091(4) 0.0245(5) Uani 1 1 d . . . . .
C13 C 0.7474(6) 0.04699(5) 0.5100(4) 0.0244(5) Uani 1 1 d . . . . .
H13 H 0.6397 0.0368 0.3873 0.029 Uiso 1 1 calc R U . . .
C14 C 0.8091(6) 0.07560(5) 0.4921(4) 0.0219(5) Uani 1 1 d . . . . .
H14 H 0.7388 0.0852 0.3567 0.026 Uiso 1 1 calc R U . . .
C15 C 0.7858(6) 0.13609(4) 0.3113(4) 0.0191(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C12 1.353(3) . ?
N1 C2 1.332(3) . ?
N1 C4 1.339(3) . ?
N2 C15 1.148(3) . ?
C1 C2 1.396(3) . ?
C1 C6 1.397(3) . ?
C1 C7 1.480(3) . ?
C2 H2 0.9500 . ?
C4 C5 1.387(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.377(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.356(3) . ?
C7 C15 1.438(3) . ?
C8 C9 1.460(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.405(3) . ?
C9 C14 1.406(3) . ?
C10 C11 1.382(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.380(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.380(3) . ?
C13 C14 1.378(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C4 116.8(2) . . ?
C2 C1 C6 116.2(2) . . ?
C2 C1 C7 120.9(2) . . ?
C6 C1 C7 122.81(19) . . ?
N1 C2 C1 125.2(2) . . ?
N1 C2 H2 117.4 . . ?
C1 C2 H2 117.4 . . ?
N1 C4 C5 123.1(2) . . ?
N1 C4 H4 118.4 . . ?
C5 C4 H4 118.4 . . ?
C6 C5 C4 119.0(2) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C1 119.7(2) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
C8 C7 C15 121.2(2) . . ?
C8 C7 C1 123.3(2) . . ?
C15 C7 C1 115.41(18) . . ?
C7 C8 C9 131.9(2) . . ?
C7 C8 H8 114.0 . . ?
C9 C8 H8 114.0 . . ?
C10 C9 C14 117.5(2) . . ?
C10 C9 C8 116.12(19) . . ?
C14 C9 C8 126.34(19) . . ?
C11 C10 C9 121.8(2) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C12 C11 C10 118.1(2) . . ?
C12 C11 H11 120.9 . . ?
C10 C11 H11 120.9 . . ?
F1 C12 C11 118.9(2) . . ?
F1 C12 C13 118.8(2) . . ?
C11 C12 C13 122.3(2) . . ?
C14 C13 C12 118.9(2) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C14 C9 121.2(2) . . ?
C13 C14 H14 119.4 . . ?
C9 C14 H14 119.4 . . ?
N2 C15 C7 177.7(2) . . ?

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
C4 N1 C2 C1 -1.1(4) . . . . ?
C6 C1 C2 N1 1.3(3) . . . . ?
C7 C1 C2 N1 -178.1(2) . . . . ?
C2 N1 C4 C5 -0.4(4) . . . . ?
N1 C4 C5 C6 1.6(4) . . . . ?
C4 C5 C6 C1 -1.3(3) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
C7 C1 C6 C5 179.4(2) . . . . ?
C2 C1 C7 C8 169.0(2) . . . . ?
C6 C1 C7 C8 -10.4(3) . . . . ?
C2 C1 C7 C15 -10.1(3) . . . . ?
C6 C1 C7 C15 170.47(19) . . . . ?
C15 C7 C8 C9 -0.1(4) . . . . ?
C1 C7 C8 C9 -179.2(2) . . . . ?
C7 C8 C9 C10 -175.1(2) . . . . ?
C7 C8 C9 C14 5.2(4) . . . . ?
C14 C9 C10 C11 -0.2(3) . . . . ?
C8 C9 C10 C11 -179.9(2) . . . . ?
C9 C10 C11 C12 -0.2(3) . . . . ?
C10 C11 C12 F1 -179.5(2) . . . . ?
C10 C11 C12 C13 1.2(3) . . . . ?
F1 C12 C13 C14 179.0(2) . . . . ?
C11 C12 C13 C14 -1.6(4) . . . . ?
C12 C13 C14 C9 1.2(3) . . . . ?
C10 C9 C14 C13 -0.3(3) . . . . ?
C8 C9 C14 C13 179.3(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 N2 0.95 2.81 3.479(3) 127.8 .
C14 H14 N2 0.95 2.59 3.440(3) 148.9 .
C11 H11 F1 0.95 2.55 3.441(3) 156.8 3_757
C13 H13 F1 0.95 2.62 3.440(3) 145.3 3_656
C4 H4 N1 0.95 2.62 3.416(3) 142.1 4_666
C8 H8 N2 0.95 2.58 3.511(3) 165.7 1_656


_refine_diff_density_max         0.323
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.059

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_2py4f
_database_code_depnum_ccdc_archive 'CCDC 1544814'
_audit_update_record             
;
2017-04-18 deposited with the CCDC.
2018-03-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
(Z)-3-(4-fluorophenyl)-2-(pyridin-2-yl)acrylonitrile
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H9 F N2'
_chemical_formula_sum            'C14 H9 F N2'
_chemical_formula_weight         224.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   3.78230(11)
_cell_length_b                   22.3928(6)
_cell_length_c                   12.7185(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.041(3)
_cell_angle_gamma                90
_cell_volume                     1077.03(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3451
_cell_measurement_theta_min      3.93
_cell_measurement_theta_max      71.75
_exptl_crystal_description       lath
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.783
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.821
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
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_special_details           
;
 ?
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3875
_diffrn_reflns_number            6335
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.948
_diffrn_reflns_theta_max         71.883
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2117
_reflns_number_gt                1910
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0439P)²+0.3162P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0025(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2117
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0902
_refine_ls_wR_factor_gt          0.0865
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.3828(2) 0.57794(3) 0.47233(6) 0.0294(2) Uani 1 1 d . . . . .
N1 N 0.9141(3) 0.91088(4) 0.23859(8) 0.0220(2) Uani 1 1 d . . . . .
N2 N 1.1955(3) 0.85324(5) 0.58966(8) 0.0306(3) Uani 1 1 d . . . . .
C1 C 1.0185(3) 0.91043(5) 0.34019(9) 0.0197(2) Uani 1 1 d . . . . .
C3 C 0.9664(3) 0.96097(5) 0.18419(9) 0.0234(3) Uani 1 1 d . . . . .
H3 H 0.8918 0.9618 0.1125 0.028 Uiso 1 1 calc R U . . .
C4 C 1.1235(3) 1.01196(5) 0.22628(10) 0.0244(3) Uani 1 1 d . . . . .
H4 H 1.1557 1.0466 0.1843 0.029 Uiso 1 1 calc R U . . .
C5 C 1.2317(3) 1.01114(5) 0.33057(10) 0.0250(3) Uani 1 1 d . . . . .
H5 H 1.3405 1.0452 0.3618 0.030 Uiso 1 1 calc R U . . .
C6 C 1.1781(3) 0.95949(5) 0.38891(10) 0.0228(3) Uani 1 1 d . . . . .
H6 H 1.2493 0.9577 0.4609 0.027 Uiso 1 1 calc R U . . .
C7 C 0.9488(3) 0.85402(5) 0.39859(9) 0.0196(3) Uani 1 1 d . . . . .
C8 C 0.7741(3) 0.80795(5) 0.35312(9) 0.0206(3) Uani 1 1 d . . . . .
H8 H 0.6998 0.8155 0.2826 0.025 Uiso 1 1 calc R U . . .
C9 C 0.6772(3) 0.74881(5) 0.39106(9) 0.0197(3) Uani 1 1 d . . . . .
C10 C 0.5207(3) 0.71018(5) 0.31705(9) 0.0214(3) Uani 1 1 d . . . . .
H10 H 0.4823 0.7238 0.2471 0.026 Uiso 1 1 calc R U . . .
C11 C 0.4204(3) 0.65263(5) 0.34317(9) 0.0220(3) Uani 1 1 d . . . . .
H11 H 0.3149 0.6267 0.2924 0.026 Uiso 1 1 calc R U . . .
C12 C 0.4792(3) 0.63436(5) 0.44530(9) 0.0224(3) Uani 1 1 d . . . . .
C13 C 0.6322(3) 0.67028(5) 0.52179(9) 0.0234(3) Uani 1 1 d . . . . .
H13 H 0.6692 0.6560 0.5915 0.028 Uiso 1 1 calc R U . . .
C14 C 0.7306(3) 0.72778(5) 0.49422(9) 0.0222(3) Uani 1 1 d . . . . .
H14 H 0.8353 0.7533 0.5457 0.027 Uiso 1 1 calc R U . . .
C15 C 1.0823(3) 0.85231(5) 0.50544(9) 0.0225(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C12 1.3609(13) . ?
N1 C3 1.3344(15) . ?
N1 C1 1.3445(15) . ?
N2 C15 1.1465(16) . ?
C1 C6 1.3935(16) . ?
C1 C7 1.4914(16) . ?
C3 C4 1.3899(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.3811(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.3908(17) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.3494(16) . ?
C7 C15 1.4417(15) . ?
C8 C9 1.4585(16) . ?
C8 H8 0.9500 . ?
C9 C10 1.4015(16) . ?
C9 C14 1.4052(16) . ?
C10 C11 1.3856(16) . ?
C10 H10 0.9500 . ?
C11 C12 1.3761(16) . ?
C11 H11 0.9500 . ?
C12 C13 1.3812(17) . ?
C13 C14 1.3872(17) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?

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
C3 N1 C1 117.45(10) . . ?
N1 C1 C6 122.60(11) . . ?
N1 C1 C7 115.69(10) . . ?
C6 C1 C7 121.71(10) . . ?
N1 C3 C4 123.85(11) . . ?
N1 C3 H3 118.1 . . ?
C4 C3 H3 118.1 . . ?
C5 C4 C3 118.44(11) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C4 C5 C6 118.68(11) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C5 C6 C1 118.98(11) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
C8 C7 C15 122.96(10) . . ?
C8 C7 C1 121.58(10) . . ?
C15 C7 C1 115.45(10) . . ?
C7 C8 C9 132.55(11) . . ?
C7 C8 H8 113.7 . . ?
C9 C8 H8 113.7 . . ?
C10 C9 C14 118.16(11) . . ?
C10 C9 C8 116.35(10) . . ?
C14 C9 C8 125.49(11) . . ?
C11 C10 C9 121.82(11) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C12 C11 C10 117.54(11) . . ?
C12 C11 H11 121.2 . . ?
C10 C11 H11 121.2 . . ?
F1 C12 C11 118.35(11) . . ?
F1 C12 C13 118.26(11) . . ?
C11 C12 C13 123.39(11) . . ?
C12 C13 C14 118.25(11) . . ?
C12 C13 H13 120.9 . . ?
C14 C13 H13 120.9 . . ?
C13 C14 C9 120.83(11) . . ?
C13 C14 H14 119.6 . . ?
C9 C14 H14 119.6 . . ?
N2 C15 C7 177.08(13) . . ?

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
C3 N1 C1 C6 -0.43(16) . . . . ?
C3 N1 C1 C7 178.85(10) . . . . ?
C1 N1 C3 C4 0.47(17) . . . . ?
N1 C3 C4 C5 -0.19(18) . . . . ?
C3 C4 C5 C6 -0.14(17) . . . . ?
C4 C5 C6 C1 0.18(17) . . . . ?
N1 C1 C6 C5 0.11(17) . . . . ?
C7 C1 C6 C5 -179.13(11) . . . . ?
N1 C1 C7 C8 -3.56(16) . . . . ?
C6 C1 C7 C8 175.73(11) . . . . ?
N1 C1 C7 C15 176.03(10) . . . . ?
C6 C1 C7 C15 -4.68(16) . . . . ?
C15 C7 C8 C9 -0.5(2) . . . . ?
C1 C7 C8 C9 179.02(11) . . . . ?
C7 C8 C9 C10 -174.37(12) . . . . ?
C7 C8 C9 C14 5.1(2) . . . . ?
C14 C9 C10 C11 -0.18(17) . . . . ?
C8 C9 C10 C11 179.29(10) . . . . ?
C9 C10 C11 C12 0.12(17) . . . . ?
C10 C11 C12 F1 -179.92(10) . . . . ?
C10 C11 C12 C13 -0.13(18) . . . . ?
F1 C12 C13 C14 179.99(10) . . . . ?
C11 C12 C13 C14 0.20(18) . . . . ?
C12 C13 C14 C9 -0.26(17) . . . . ?
C10 C9 C14 C13 0.26(17) . . . . ?
C8 C9 C14 C13 -179.17(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6 N2 0.95 2.87 3.4898(17) 124.3 .
C14 H14 N2 0.95 2.67 3.5184(16) 148.4 .
C13 H13 N1 0.95 2.56 3.4547(15) 157.7 4_576
C5 H5 N2 0.95 2.93 3.8558(16) 164.5 3_876
C11 H11 N2 0.95 2.65 3.3223(15) 128.3 4_475

_refine_diff_density_max         0.212
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.039

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane: chloroform'
_exptl_crystal_preparation       ', Luminescent'
####################################################################### 
# 
# 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_2py4cl
_database_code_depnum_ccdc_archive 'CCDC 1544815'
_audit_update_record             
;
2017-04-18 deposited with the CCDC.
2018-03-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
(Z)-3-(4-chlorophenyl)-2-(pyridin-2-yl)acrylonitrile
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H9 Cl N2'
_chemical_formula_sum            'C14 H9 Cl N2'
_chemical_formula_weight         240.68

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'
Cl Cl 0.1484 0.1585 '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 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   11.6356(5)
_cell_length_b                   3.82523(14)
_cell_length_c                   25.2133(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.488(4)
_cell_angle_gamma                90
_cell_volume                     1121.84(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    2958
_cell_measurement_theta_min      1.75
_cell_measurement_theta_max      26.31

_exptl_crystal_description       lath
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.09
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    0.315
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.885
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
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_special_details           
; 
 ? 
;
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Goniometer KM4/Xcalibur, detector: Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.989
_diffrn_reflns_number            7069
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.954
_diffrn_reflns_theta_max         26.244
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2270
_reflns_number_gt                1879
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0541P)²+0.4003P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2270
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.1056
_refine_ls_wR_factor_gt          0.0996
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.15002(4) -0.01214(11) 0.13616(2) 0.02900(16) Uani 1 1 d . . . . .
N1 N -0.29744(11) -0.1076(4) 0.40713(5) 0.0215(3) Uani 1 1 d . . . . .
N2 N 0.06576(12) 0.4634(4) 0.41374(6) 0.0246(3) Uani 1 1 d . . . . .
C1 C -0.19758(13) 0.0385(4) 0.42365(6) 0.0180(3) Uani 1 1 d . . . . .
C3 C -0.37211(14) -0.1900(4) 0.44415(7) 0.0233(4) Uani 1 1 d . . . . .
H3 H -0.4429 -0.2932 0.4329 0.028 Uiso 1 1 calc R U . . .
C4 C -0.35339(14) -0.1351(4) 0.49819(7) 0.0237(4) Uani 1 1 d . . . . .
H4 H -0.4093 -0.2010 0.5231 0.028 Uiso 1 1 calc R U . . .
C5 C -0.25105(14) 0.0181(4) 0.51459(7) 0.0231(4) Uani 1 1 d . . . . .
H5 H -0.2352 0.0614 0.5512 0.028 Uiso 1 1 calc R U . . .
C6 C -0.17215(14) 0.1074(4) 0.47701(6) 0.0205(3) Uani 1 1 d . . . . .
H6 H -0.1014 0.2144 0.4873 0.025 Uiso 1 1 calc R U . . .
C7 C -0.11393(13) 0.1151(4) 0.38172(6) 0.0178(3) Uani 1 1 d . . . . .
C8 C -0.13121(13) 0.0028(4) 0.33123(6) 0.0172(3) Uani 1 1 d . . . . .
H8 H -0.2031 -0.1095 0.3249 0.021 Uiso 1 1 calc R U . . .
C9 C -0.05935(13) 0.0235(4) 0.28490(6) 0.0175(3) Uani 1 1 d . . . . .
C10 C -0.10540(13) -0.1151(4) 0.23719(6) 0.0190(3) Uani 1 1 d . . . . .
H10 H -0.1815 -0.2056 0.2367 0.023 Uiso 1 1 calc R U . . .
C11 C -0.04399(14) -0.1242(4) 0.19113(6) 0.0212(4) Uani 1 1 d . . . . .
H11 H -0.0769 -0.2191 0.1594 0.025 Uiso 1 1 calc R U . . .
C12 C 0.06655(14) 0.0080(4) 0.19229(7) 0.0199(3) Uani 1 1 d . . . . .
C13 C 0.11460(13) 0.1532(4) 0.23835(7) 0.0212(4) Uani 1 1 d . . . . .
H13 H 0.1901 0.2476 0.2382 0.025 Uiso 1 1 calc R U . . .
C14 C 0.05264(13) 0.1601(4) 0.28415(7) 0.0206(3) Uani 1 1 d . . . . .
H14 H 0.0860 0.2582 0.3156 0.025 Uiso 1 1 calc R U . . .
C15 C -0.01244(13) 0.3046(4) 0.39869(6) 0.0194(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C12 1.7388(17) . ?
N1 C3 1.330(2) . ?
N1 C1 1.346(2) . ?
N2 C15 1.150(2) . ?
C1 C6 1.395(2) . ?
C1 C7 1.485(2) . ?
C3 C4 1.390(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.379(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.354(2) . ?
C7 C15 1.441(2) . ?
C8 C9 1.456(2) . ?
C8 H8 0.9500 . ?
C9 C14 1.404(2) . ?
C9 C10 1.408(2) . ?
C10 C11 1.380(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.382(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.391(2) . ?
C13 C14 1.378(2) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?

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
C3 N1 C1 117.12(14) . . ?
N1 C1 C6 122.46(15) . . ?
N1 C1 C7 115.99(14) . . ?
C6 C1 C7 121.53(14) . . ?
N1 C3 C4 124.31(15) . . ?
N1 C3 H3 117.8 . . ?
C4 C3 H3 117.8 . . ?
C5 C4 C3 118.01(16) . . ?
C5 C4 H4 121.0 . . ?
C3 C4 H4 121.0 . . ?
C6 C5 C4 118.91(15) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C1 119.18(15) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
C8 C7 C15 122.64(15) . . ?
C8 C7 C1 121.54(14) . . ?
C15 C7 C1 115.79(13) . . ?
C7 C8 C9 131.52(14) . . ?
C7 C8 H8 114.2 . . ?
C9 C8 H8 114.2 . . ?
C14 C9 C10 117.47(15) . . ?
C14 C9 C8 125.68(14) . . ?
C10 C9 C8 116.82(14) . . ?
C11 C10 C9 122.33(15) . . ?
C11 C10 H10 118.8 . . ?
C9 C10 H10 118.8 . . ?
C10 C11 C12 118.37(15) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 H11 120.8 . . ?
C11 C12 C13 121.16(15) . . ?
C11 C12 Cl1 120.40(13) . . ?
C13 C12 Cl1 118.43(12) . . ?
C14 C13 C12 119.97(14) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C9 120.68(14) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?
N2 C15 C7 177.10(17) . . ?

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
C3 N1 C1 C6 -0.8(2) . . . . ?
C3 N1 C1 C7 177.69(14) . . . . ?
C1 N1 C3 C4 0.0(2) . . . . ?
N1 C3 C4 C5 0.7(3) . . . . ?
C3 C4 C5 C6 -0.4(2) . . . . ?
C4 C5 C6 C1 -0.4(2) . . . . ?
N1 C1 C6 C5 1.1(2) . . . . ?
C7 C1 C6 C5 -177.37(14) . . . . ?
N1 C1 C7 C8 -8.3(2) . . . . ?
C6 C1 C7 C8 170.24(15) . . . . ?
N1 C1 C7 C15 173.70(13) . . . . ?
C6 C1 C7 C15 -7.8(2) . . . . ?
C15 C7 C8 C9 2.7(3) . . . . ?
C1 C7 C8 C9 -175.19(14) . . . . ?
C7 C8 C9 C14 3.4(3) . . . . ?
C7 C8 C9 C10 -178.57(16) . . . . ?
C14 C9 C10 C11 0.9(2) . . . . ?
C8 C9 C10 C11 -177.26(14) . . . . ?
C9 C10 C11 C12 0.0(2) . . . . ?
C10 C11 C12 C13 -1.2(2) . . . . ?
C10 C11 C12 Cl1 177.47(12) . . . . ?
C11 C12 C13 C14 1.4(2) . . . . ?
Cl1 C12 C13 C14 -177.29(12) . . . . ?
C12 C13 C14 C9 -0.4(2) . . . . ?
C10 C9 C14 C13 -0.7(2) . . . . ?
C8 C9 C14 C13 177.29(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6 N2 0.95 2.88 3.506(2) 124.1 .
C14 H14 N2 0.95 2.61 3.467(2) 149.7 .
C11 H11 N1 0.95 2.65 3.567(2) 161.9 2_445
C5 H5 N2 0.95 2.81 3.412(2) 122.4 3_566
C6 H6 N2 0.95 2.80 3.411(2) 122.7 3_566

_refine_diff_density_max         0.382
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.054

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane: chloroform'
_exptl_crystal_preparation       ', Luminescent'
####################################################################### 
# 
# 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_3py4br
_database_code_depnum_ccdc_archive 'CCDC 1544816'
_audit_update_record             
;
2017-04-18 deposited with the CCDC.
2018-03-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
(Z)-3-(4-bromophenyl)-2-(pyridin-3-yl)acrylonitrile
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H9 Br N2'
_chemical_formula_sum            'C14 H9 Br N2'
_chemical_formula_weight         285.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   4.77341(15)
_cell_length_b                   15.3325(5)
_cell_length_c                   15.7201(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1150.53(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    7018
_cell_measurement_theta_min      3.99
_cell_measurement_theta_max      72.09
_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    4.662
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.512
_exptl_absorpt_correction_T_max  0.877
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            9841
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_av_R_equivalents  0.0789
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.027
_diffrn_reflns_theta_max         71.855
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             2222
_reflns_number_gt                2018
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.668
_reflns_Friedel_fraction_max     0.982
_reflns_Friedel_fraction_full    0.982

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0566P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 773 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2222
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.0863
_refine_ls_wR_factor_gt          0.0851
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 1.0870(12) 0.3560(3) -0.0411(2) 0.0219(10) Uani 1 1 d . . . . .
N2 N 0.5854(14) 0.5470(3) 0.2402(3) 0.0336(12) Uani 1 1 d . . . . .
Br1 Br -0.43868(13) 0.23691(3) 0.41675(3) 0.02503(18) Uani 1 1 d . . . . .
C1 C 0.8065(13) 0.4238(3) 0.0687(3) 0.0185(10) Uani 1 1 d . . . . .
C2 C 0.9017(14) 0.3515(3) 0.0222(3) 0.0216(12) Uani 1 1 d . . . . .
H2 H 0.8293 0.2957 0.0367 0.026 Uiso 1 1 calc R U . . .
C4 C 1.1921(14) 0.4353(3) -0.0608(3) 0.0236(11) Uani 1 1 d . . . . .
H4 H 1.3256 0.4396 -0.1054 0.028 Uiso 1 1 calc R U . . .
C5 C 1.1129(13) 0.5107(3) -0.0183(3) 0.0248(13) Uani 1 1 d . . . . .
H5 H 1.1901 0.5655 -0.0340 0.030 Uiso 1 1 calc R U . . .
C6 C 0.9202(15) 0.5050(3) 0.0470(3) 0.0228(11) Uani 1 1 d . . . . .
H6 H 0.8650 0.5559 0.0771 0.027 Uiso 1 1 calc R U . . .
C7 C 0.6008(13) 0.4145(3) 0.1388(3) 0.0188(11) Uani 1 1 d . . . . .
C8 C 0.4465(14) 0.3422(3) 0.1517(3) 0.0186(10) Uani 1 1 d . . . . .
H8 H 0.4817 0.2963 0.1126 0.022 Uiso 1 1 calc R U . . .
C9 C 0.2324(12) 0.3223(3) 0.2163(3) 0.0198(11) Uani 1 1 d . . . . .
C10 C 0.1290(12) 0.2376(3) 0.2168(3) 0.0220(11) Uani 1 1 d . . . . .
H10 H 0.1991 0.1967 0.1767 0.026 Uiso 1 1 calc R U . . .
C11 C -0.0760(14) 0.2110(3) 0.2750(3) 0.0228(11) Uani 1 1 d . . . . .
H11 H -0.1489 0.1534 0.2736 0.027 Uiso 1 1 calc R U . . .
C12 C -0.1697(12) 0.2707(3) 0.3346(3) 0.0203(10) Uani 1 1 d . . . . .
C13 C -0.0754(15) 0.3559(3) 0.3351(3) 0.0225(10) Uani 1 1 d . . . . .
H13 H -0.1487 0.3966 0.3749 0.027 Uiso 1 1 calc R U . . .
C14 C 0.1287(13) 0.3817(3) 0.2765(3) 0.0223(12) Uani 1 1 d . . . . .
H14 H 0.1978 0.4397 0.2775 0.027 Uiso 1 1 calc R U . . .
C15 C 0.5866(15) 0.4886(3) 0.1955(3) 0.0244(12) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.333(8) . ?
N1 C4 1.351(7) . ?
N2 C15 1.138(7) . ?
Br1 C12 1.894(5) . ?
C1 C6 1.400(7) . ?
C1 C2 1.404(7) . ?
C1 C7 1.483(7) . ?
C2 H2 0.9500 . ?
C4 C5 1.387(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(8) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.346(7) . ?
C7 C15 1.446(6) . ?
C8 C9 1.473(8) . ?
C8 H8 0.9500 . ?
C9 C10 1.390(7) . ?
C9 C14 1.403(7) . ?
C10 C11 1.400(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.382(8) . ?
C13 C14 1.397(8) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C4 117.6(4) . . ?
C6 C1 C2 116.7(5) . . ?
C6 C1 C7 121.6(4) . . ?
C2 C1 C7 121.7(4) . . ?
N1 C2 C1 124.2(5) . . ?
N1 C2 H2 117.9 . . ?
C1 C2 H2 117.9 . . ?
N1 C4 C5 122.6(5) . . ?
N1 C4 H4 118.7 . . ?
C5 C4 H4 118.7 . . ?
C6 C5 C4 119.1(5) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C1 119.7(5) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
C8 C7 C15 122.0(5) . . ?
C8 C7 C1 123.6(4) . . ?
C15 C7 C1 114.4(5) . . ?
C7 C8 C9 130.8(4) . . ?
C7 C8 H8 114.6 . . ?
C9 C8 H8 114.6 . . ?
C10 C9 C14 118.4(5) . . ?
C10 C9 C8 116.4(4) . . ?
C14 C9 C8 125.2(5) . . ?
C9 C10 C11 121.6(5) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
C12 C11 C10 118.4(5) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
C13 C12 C11 121.6(5) . . ?
C13 C12 Br1 118.4(4) . . ?
C11 C12 Br1 120.0(4) . . ?
C12 C13 C14 119.3(5) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C13 C14 C9 120.5(5) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?
N2 C15 C7 177.6(8) . . ?

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
C4 N1 C2 C1 0.9(9) . . . . ?
C6 C1 C2 N1 -1.1(9) . . . . ?
C7 C1 C2 N1 -179.7(5) . . . . ?
C2 N1 C4 C5 -0.5(9) . . . . ?
N1 C4 C5 C6 0.4(9) . . . . ?
C4 C5 C6 C1 -0.6(9) . . . . ?
C2 C1 C6 C5 0.9(8) . . . . ?
C7 C1 C6 C5 179.5(5) . . . . ?
C6 C1 C7 C8 166.8(6) . . . . ?
C2 C1 C7 C8 -14.7(8) . . . . ?
C6 C1 C7 C15 -15.7(7) . . . . ?
C2 C1 C7 C15 162.8(5) . . . . ?
C15 C7 C8 C9 3.8(10) . . . . ?
C1 C7 C8 C9 -178.9(5) . . . . ?
C7 C8 C9 C10 -174.3(6) . . . . ?
C7 C8 C9 C14 5.3(10) . . . . ?
C14 C9 C10 C11 0.7(8) . . . . ?
C8 C9 C10 C11 -179.7(5) . . . . ?
C9 C10 C11 C12 -1.9(8) . . . . ?
C10 C11 C12 C13 3.0(8) . . . . ?
C10 C11 C12 Br1 -178.1(4) . . . . ?
C11 C12 C13 C14 -2.9(9) . . . . ?
Br1 C12 C13 C14 178.2(4) . . . . ?
C12 C13 C14 C9 1.6(9) . . . . ?
C10 C9 C14 C13 -0.5(8) . . . . ?
C8 C9 C14 C13 179.9(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6 N2 0.95 2.89 3.492(7) 122.0 .
C14 H14 N2 0.95 2.54 3.392(7) 148.8 .
C2 H2 N1 0.95 2.60 3.531(7) 166.9 3_455
C8 H8 N1 0.95 2.64 3.565(6) 164.8 3_455
C10 H10 N2 0.95 2.83 3.295(7) 110.9 4_645
C11 H11 N2 0.95 2.66 3.507(8) 149.4 4_545

_refine_diff_density_max         0.731
_refine_diff_density_min         -0.667
_refine_diff_density_rms         0.096

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane:chloroform'
_exptl_crystal_preparation       ', Luminescent'
####################################################################### 
# 
# 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_4py4cl
_database_code_depnum_ccdc_archive 'CCDC 1544818'
_audit_update_record             
;
2017-04-18 deposited with the CCDC.
2018-03-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H9 Cl N2'
_chemical_formula_sum            'C14 H9 Cl N2'
_chemical_formula_weight         240.68

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   3.82480(7)
_cell_length_b                   5.96310(10)
_cell_length_c                   48.2653(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1100.82(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    10266
_cell_measurement_theta_min      3.65
_cell_measurement_theta_max      72.08

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    2.853
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.463
_exptl_absorpt_correction_T_max  0.875
_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_special_details           
;
 ?
;

_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            15920
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -58
_diffrn_reflns_limit_l_max       59
_diffrn_reflns_theta_min         3.663
_diffrn_reflns_theta_max         71.832
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2163
_reflns_number_gt                2155
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.593
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+4.1021P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 800 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.027(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2163
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0545
_refine_ls_wR_factor_ref         0.1262
_refine_ls_wR_factor_gt          0.1262
_refine_ls_goodness_of_fit_ref   1.178
_refine_ls_restrained_S_all      1.178
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.5268(3) 0.5028(2) 0.00739(2) 0.0215(3) Uani 1 1 d . . . . .
N1 N 1.1953(13) 0.7142(8) 0.23129(9) 0.0225(10) Uani 1 1 d . . . . .
N2 N 1.3811(12) 0.1449(8) 0.13479(9) 0.0227(10) Uani 1 1 d . . . . .
C1 C 1.1238(13) 0.5975(9) 0.17496(10) 0.0166(10) Uani 1 1 d . . . . .
C2 C 1.0062(15) 0.8045(8) 0.18479(10) 0.0191(10) Uani 1 1 d . . . . .
H2 H 0.9006 0.9095 0.1726 0.023 Uiso 1 1 calc R U . . .
C3 C 1.0465(15) 0.8540(9) 0.21278(10) 0.0217(11) Uani 1 1 d . . . . .
H3 H 0.9642 0.9949 0.2192 0.026 Uiso 1 1 calc R U . . .
C5 C 1.3092(14) 0.5181(10) 0.22141(10) 0.0227(11) Uani 1 1 d . . . . .
H5 H 1.4166 0.4163 0.2339 0.027 Uiso 1 1 calc R U . . .
C6 C 1.2793(14) 0.4557(9) 0.19405(11) 0.0210(11) Uani 1 1 d . . . . .
H6 H 1.3660 0.3141 0.1882 0.025 Uiso 1 1 calc R U . . .
C7 C 1.0861(13) 0.5306(9) 0.14529(10) 0.0173(10) Uani 1 1 d . . . . .
C8 C 0.9154(13) 0.6496(9) 0.12598(10) 0.0161(10) Uani 1 1 d . . . . .
H8 H 0.8262 0.7885 0.1325 0.019 Uiso 1 1 calc R U . . .
C9 C 0.8405(13) 0.6066(8) 0.09687(10) 0.0146(10) Uani 1 1 d . . . . .
C10 C 0.6743(14) 0.7762(8) 0.08169(10) 0.0172(11) Uani 1 1 d . . . . .
H10 H 0.6217 0.9140 0.0906 0.021 Uiso 1 1 calc R U . . .
C11 C 0.5845(14) 0.7497(8) 0.05418(10) 0.0166(10) Uani 1 1 d . . . . .
H11 H 0.4743 0.8676 0.0442 0.020 Uiso 1 1 calc R U . . .
C12 C 0.6593(13) 0.5465(8) 0.04141(10) 0.0163(11) Uani 1 1 d . . . . .
C13 C 0.8226(14) 0.3742(9) 0.05553(10) 0.0182(11) Uani 1 1 d . . . . .
H13 H 0.8713 0.2362 0.0465 0.022 Uiso 1 1 calc R U . . .
C14 C 0.9146(14) 0.4047(8) 0.08307(10) 0.0177(11) Uani 1 1 d . . . . .
H14 H 1.0296 0.2872 0.0928 0.021 Uiso 1 1 calc R U . . .
C15 C 1.2442(14) 0.3134(9) 0.13881(10) 0.0175(11) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C12 1.738(5) . ?
N1 C5 1.336(7) . ?
N1 C3 1.348(7) . ?
N2 C15 1.150(7) . ?
C1 C6 1.384(7) . ?
C1 C2 1.397(7) . ?
C1 C7 1.493(7) . ?
C2 C3 1.392(7) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C5 C6 1.377(7) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.341(7) . ?
C7 C15 1.463(7) . ?
C8 C9 1.457(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.401(7) . ?
C9 C14 1.405(7) . ?
C10 C11 1.381(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.382(7) . ?
C13 C14 1.387(7) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?

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 C3 116.3(4) . . ?
C6 C1 C2 116.9(5) . . ?
C6 C1 C7 121.1(5) . . ?
C2 C1 C7 122.0(5) . . ?
C3 C2 C1 118.8(5) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
N1 C3 C2 124.0(5) . . ?
N1 C3 H3 118.0 . . ?
C2 C3 H3 118.0 . . ?
N1 C5 C6 123.5(5) . . ?
N1 C5 H5 118.3 . . ?
C6 C5 H5 118.3 . . ?
C5 C6 C1 120.6(5) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
C8 C7 C15 121.4(5) . . ?
C8 C7 C1 124.9(5) . . ?
C15 C7 C1 113.7(4) . . ?
C7 C8 C9 132.3(5) . . ?
C7 C8 H8 113.9 . . ?
C9 C8 H8 113.9 . . ?
C10 C9 C14 117.5(5) . . ?
C10 C9 C8 117.8(5) . . ?
C14 C9 C8 124.7(5) . . ?
C11 C10 C9 122.2(5) . . ?
C11 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?
C10 C11 C12 118.4(5) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 H11 120.8 . . ?
C13 C12 C11 121.5(4) . . ?
C13 C12 Cl1 119.1(4) . . ?
C11 C12 Cl1 119.3(4) . . ?
C12 C13 C14 119.3(5) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C13 C14 C9 121.0(5) . . ?
C13 C14 H14 119.5 . . ?
C9 C14 H14 119.5 . . ?
N2 C15 C7 176.4(6) . . ?

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
C6 C1 C2 C3 -1.0(8) . . . . ?
C7 C1 C2 C3 179.2(5) . . . . ?
C5 N1 C3 C2 0.3(8) . . . . ?
C1 C2 C3 N1 0.4(9) . . . . ?
C3 N1 C5 C6 -0.4(8) . . . . ?
N1 C5 C6 C1 -0.2(9) . . . . ?
C2 C1 C6 C5 0.9(8) . . . . ?
C7 C1 C6 C5 -179.3(5) . . . . ?
C6 C1 C7 C8 174.5(5) . . . . ?
C2 C1 C7 C8 -5.7(8) . . . . ?
C6 C1 C7 C15 -3.3(7) . . . . ?
C2 C1 C7 C15 176.5(5) . . . . ?
C15 C7 C8 C9 0.7(9) . . . . ?
C1 C7 C8 C9 -177.0(5) . . . . ?
C7 C8 C9 C10 -175.4(5) . . . . ?
C7 C8 C9 C14 6.4(9) . . . . ?
C14 C9 C10 C11 0.0(8) . . . . ?
C8 C9 C10 C11 -178.4(5) . . . . ?
C9 C10 C11 C12 0.7(8) . . . . ?
C10 C11 C12 C13 -0.6(8) . . . . ?
C10 C11 C12 Cl1 176.4(4) . . . . ?
C11 C12 C13 C14 -0.1(8) . . . . ?
Cl1 C12 C13 C14 -177.1(4) . . . . ?
C12 C13 C14 C9 0.8(8) . . . . ?
C10 C9 C14 C13 -0.7(8) . . . . ?
C8 C9 C14 C13 177.5(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6 N2 0.95 2.77 3.431(7) 127.4 .
C14 H14 N2 0.95 2.58 3.437(7) 150.6 .
C8 H8 N2 0.95 2.73 3.617(7) 156.5 1_465
C10 H10 N2 0.95 2.70 3.558(7) 150.7 1_465
C2 H2 N2 0.95 2.95 3.464(7) 115.7 1_565
C8 H8 N2 0.95 2.73 3.617(7) 156.5 1_465
C10 H10 N2 0.95 2.70 3.558(7) 150.7 1_465
C3 H3 N1 0.95 2.79 3.572(7) 140.2 3_755
C5 H5 N1 0.95 2.54 3.477(7) 167.1 3_845

_refine_diff_density_max         0.589
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.091

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_4py4br
_database_code_depnum_ccdc_archive 'CCDC 1544817'
_audit_update_record             
;
2017-04-18 deposited with the CCDC.
2018-03-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
(Z)-3-(4-bromophenyl)-2-(pyridin-4-yl)acrylonitrile
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H9 Br N2'
_chemical_formula_sum            'C14 H9 Br N2'
_chemical_formula_weight         285.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.4111(2)
_cell_length_b                   15.5974(5)
_cell_length_c                   10.2178(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.820(3)
_cell_angle_gamma                90
_cell_volume                     1146.92(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    3906
_cell_measurement_theta_min      5.24
_cell_measurement_theta_max      72.06

_exptl_crystal_description       'small rod'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.651
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    4.677
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.557
_exptl_absorpt_correction_T_max  0.871
_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_special_details           
;
 ?
;

_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            7615

_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         5.283
_diffrn_reflns_theta_max         71.885
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2260
_reflns_number_gt                1949
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0293P)²+0.5926P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2260
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0257
_refine_ls_wR_factor_ref         0.0665
_refine_ls_wR_factor_gt          0.0610
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.12196(3) 0.67426(2) 0.02605(2) 0.02571(9) Uani 1 1 d . . . . .
N1 N 0.5778(3) 0.26852(14) 0.9207(2) 0.0258(4) Uani 1 1 d . . . . .
N2 N 0.4590(3) 0.62481(14) 0.7345(2) 0.0336(5) Uani 1 1 d . . . . .
C1 C 0.4388(3) 0.40239(14) 0.7375(2) 0.0175(4) Uani 1 1 d . . . . .
C2 C 0.3886(3) 0.31677(15) 0.7073(2) 0.0218(5) Uani 1 1 d . . . . .
H2 H 0.3071 0.3019 0.6237 0.026 Uiso 1 1 calc R U . . .
C3 C 0.4597(3) 0.25444(15) 0.8011(3) 0.0242(5) Uani 1 1 d . . . . .
H3 H 0.4220 0.1969 0.7792 0.029 Uiso 1 1 calc R U . . .
C5 C 0.6218(3) 0.35052(16) 0.9490(2) 0.0241(5) Uani 1 1 d . . . . .
H5 H 0.7036 0.3631 1.0336 0.029 Uiso 1 1 calc R U . . .
C6 C 0.5564(3) 0.41873(15) 0.8634(2) 0.0208(5) Uani 1 1 d . . . . .
H6 H 0.5914 0.4758 0.8903 0.025 Uiso 1 1 calc R U . . .
C7 C 0.3661(3) 0.47285(14) 0.6412(2) 0.0168(4) Uani 1 1 d . . . . .
C8 C 0.2627(3) 0.45832(15) 0.5153(2) 0.0188(4) Uani 1 1 d . . . . .
H8 H 0.2435 0.3993 0.4934 0.023 Uiso 1 1 calc R U . . .
C9 C 0.1750(3) 0.51625(14) 0.4063(2) 0.0179(4) Uani 1 1 d . . . . .
C10 C 0.0904(3) 0.47629(15) 0.2840(2) 0.0200(5) Uani 1 1 d . . . . .
H10 H 0.0970 0.4157 0.2772 0.024 Uiso 1 1 calc R U . . .
C11 C -0.0027(3) 0.52292(15) 0.1729(2) 0.0207(5) Uani 1 1 d . . . . .
H11 H -0.0635 0.4947 0.0920 0.025 Uiso 1 1 calc R U . . .
C12 C -0.0053(3) 0.61146(15) 0.1823(2) 0.0199(5) Uani 1 1 d . . . . .
C13 C 0.0755(3) 0.65340(15) 0.3007(2) 0.0217(5) Uani 1 1 d . . . . .
H13 H 0.0702 0.7141 0.3056 0.026 Uiso 1 1 calc R U . . .
C14 C 0.1649(3) 0.60609(15) 0.4126(2) 0.0210(5) Uani 1 1 d . . . . .
H14 H 0.2199 0.6348 0.4944 0.025 Uiso 1 1 calc R U . . .
C15 C 0.4155(3) 0.55848(15) 0.6906(2) 0.0219(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C12 1.896(2) . ?
N1 C5 1.335(3) . ?
N1 C3 1.340(3) . ?
N2 C15 1.143(3) . ?
C1 C6 1.394(3) . ?
C1 C2 1.401(3) . ?
C1 C7 1.487(3) . ?
C2 C3 1.378(3) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C5 C6 1.389(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.350(3) . ?
C7 C15 1.444(3) . ?
C8 C9 1.460(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.403(3) . ?
C9 C14 1.406(3) . ?
C10 C11 1.385(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.385(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.380(3) . ?
C13 C14 1.389(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?

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 C3 115.3(2) . . ?
C6 C1 C2 116.9(2) . . ?
C6 C1 C7 121.5(2) . . ?
C2 C1 C7 121.6(2) . . ?
C3 C2 C1 118.8(2) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
N1 C3 C2 125.2(2) . . ?
N1 C3 H3 117.4 . . ?
C2 C3 H3 117.4 . . ?
N1 C5 C6 124.5(2) . . ?
N1 C5 H5 117.7 . . ?
C6 C5 H5 117.7 . . ?
C5 C6 C1 119.2(2) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
C8 C7 C15 121.8(2) . . ?
C8 C7 C1 122.7(2) . . ?
C15 C7 C1 115.5(2) . . ?
C7 C8 C9 132.1(2) . . ?
C7 C8 H8 113.9 . . ?
C9 C8 H8 113.9 . . ?
C10 C9 C14 117.8(2) . . ?
C10 C9 C8 115.3(2) . . ?
C14 C9 C8 126.9(2) . . ?
C11 C10 C9 121.7(2) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C12 C11 C10 118.7(2) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
C13 C12 C11 121.5(2) . . ?
C13 C12 Br1 120.55(18) . . ?
C11 C12 Br1 117.91(18) . . ?
C12 C13 C14 119.5(2) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C13 C14 C9 120.8(2) . . ?
C13 C14 H14 119.6 . . ?
C9 C14 H14 119.6 . . ?
N2 C15 C7 177.2(3) . . ?

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
C6 C1 C2 C3 -1.1(3) . . . . ?
C7 C1 C2 C3 -179.5(2) . . . . ?
C5 N1 C3 C2 2.2(4) . . . . ?
C1 C2 C3 N1 -1.1(4) . . . . ?
C3 N1 C5 C6 -1.0(3) . . . . ?
N1 C5 C6 C1 -1.1(4) . . . . ?
C2 C1 C6 C5 2.2(3) . . . . ?
C7 C1 C6 C5 -179.4(2) . . . . ?
C6 C1 C7 C8 175.2(2) . . . . ?
C2 C1 C7 C8 -6.4(3) . . . . ?
C6 C1 C7 C15 -3.9(3) . . . . ?
C2 C1 C7 C15 174.4(2) . . . . ?
C15 C7 C8 C9 -2.3(4) . . . . ?
C1 C7 C8 C9 178.6(2) . . . . ?
C7 C8 C9 C10 174.9(2) . . . . ?
C7 C8 C9 C14 -6.2(4) . . . . ?
C14 C9 C10 C11 -0.9(3) . . . . ?
C8 C9 C10 C11 178.2(2) . . . . ?
C9 C10 C11 C12 2.5(3) . . . . ?
C10 C11 C12 C13 -2.7(3) . . . . ?
C10 C11 C12 Br1 176.66(16) . . . . ?
C11 C12 C13 C14 1.2(3) . . . . ?
Br1 C12 C13 C14 -178.11(17) . . . . ?
C12 C13 C14 C9 0.5(3) . . . . ?
C10 C9 C14 C13 -0.7(3) . . . . ?
C8 C9 C14 C13 -179.6(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6 N2 0.95 2.85 3.483(3) 124.6 .
C14 H14 N2 0.95 2.67 3.496(3) 146.4 .
C2 H2 N1 0.95 2.59 3.526(3) 168.0 4_565
C13 H13 N2 0.95 2.69 3.591(3) 158.6 4_575

_refine_diff_density_max         0.312
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.066

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane:chloroform'
_exptl_crystal_preparation       ', Luminescent'
####################################################################### 
# 
# 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_3py4cl
_database_code_depnum_ccdc_archive 'CCDC 1544819'
_audit_update_record             
;
2017-04-18 deposited with the CCDC.
2018-03-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H9 Cl N2'
_chemical_formula_sum            'C14 H9 Cl N2'
_chemical_formula_weight         240.68

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   4.67306(8)
_cell_length_b                   15.4504(3)
_cell_length_c                   15.4973(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1118.92(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    10200
_cell_measurement_theta_min      1.86
_cell_measurement_theta_max      27.62

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    0.316
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.890
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug  2 2010,13:00:58)
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_special_details           
;
 ?
;
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Goniometer KM4/Xcalibur, detector: Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9890

_diffrn_reflns_number            14467
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.861
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2557
_reflns_number_gt                2411
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.680
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0356P)²+0.2263P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 958 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2557
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0267
_refine_ls_wR_factor_ref         0.0695
_refine_ls_wR_factor_gt          0.0683
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.67522(10) 0.33243(3) 1.02866(3) 0.02446(14) Uani 1 1 d . . . . .
N1 N 0.1475(4) 0.78815(10) 0.89312(10) 0.0186(3) Uani 1 1 d . . . . .
N2 N 0.6603(5) 0.49754(12) 0.71376(11) 0.0321(5) Uani 1 1 d . . . . .
C1 C 0.4358(4) 0.67432(12) 0.83082(12) 0.0149(4) Uani 1 1 d . . . . .
C2 C 0.3361(4) 0.72366(12) 0.90028(11) 0.0167(4) Uani 1 1 d . . . . .
H2 H 0.4073 0.7104 0.9562 0.020 Uiso 1 1 calc R U . . .
C4 C 0.0477(4) 0.80636(13) 0.81409(13) 0.0198(4) Uani 1 1 d . . . . .
H4 H -0.0862 0.8522 0.8079 0.024 Uiso 1 1 calc R U . . .
C5 C 0.1311(5) 0.76141(13) 0.74126(12) 0.0204(4) Uani 1 1 d . . . . .
H5 H 0.0553 0.7762 0.6863 0.025 Uiso 1 1 calc R U . . .
C6 C 0.3267(5) 0.69445(12) 0.74939(12) 0.0191(4) Uani 1 1 d . . . . .
H6 H 0.3859 0.6626 0.7001 0.023 Uiso 1 1 calc R U . . .
C7 C 0.6432(4) 0.60278(11) 0.84318(11) 0.0149(4) Uani 1 1 d . . . . .
C8 C 0.7987(4) 0.59107(11) 0.91568(12) 0.0150(4) Uani 1 1 d . . . . .
H8 H 0.7639 0.6326 0.9597 0.018 Uiso 1 1 calc R U . . .
C9 C 1.0115(4) 0.52531(12) 0.93806(12) 0.0153(4) Uani 1 1 d . . . . .
C10 C 1.1231(4) 0.52919(12) 1.02178(12) 0.0180(4) Uani 1 1 d . . . . .
H10 H 1.0568 0.5729 1.0600 0.022 Uiso 1 1 calc R U . . .
C11 C 1.3279(5) 0.47086(12) 1.05028(12) 0.0201(4) Uani 1 1 d . . . . .
H11 H 1.4027 0.4746 1.1072 0.024 Uiso 1 1 calc R U . . .
C12 C 1.4210(4) 0.40727(12) 0.99447(13) 0.0183(4) Uani 1 1 d . . . . .
C13 C 1.3189(5) 0.40181(12) 0.91089(13) 0.0196(4) Uani 1 1 d . . . . .
H13 H 1.3881 0.3583 0.8730 0.024 Uiso 1 1 calc R U . . .
C14 C 1.1145(4) 0.46061(13) 0.88301(13) 0.0187(4) Uani 1 1 d . . . . .
H14 H 1.0433 0.4569 0.8257 0.022 Uiso 1 1 calc R U . . .
C15 C 0.6604(5) 0.54344(13) 0.77154(12) 0.0203(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C12 1.7403(19) . ?
N1 C2 1.335(3) . ?
N1 C4 1.340(3) . ?
N2 C15 1.142(3) . ?
C1 C6 1.396(3) . ?
C1 C2 1.399(3) . ?
C1 C7 1.483(3) . ?
C2 H2 0.9500 . ?
C4 C5 1.381(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.350(3) . ?
C7 C15 1.442(2) . ?
C8 C9 1.464(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.399(3) . ?
C9 C14 1.400(3) . ?
C10 C11 1.387(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.379(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.383(3) . ?
C13 C14 1.387(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C4 117.54(16) . . ?
C6 C1 C2 116.91(17) . . ?
C6 C1 C7 121.44(17) . . ?
C2 C1 C7 121.64(17) . . ?
N1 C2 C1 124.24(17) . . ?
N1 C2 H2 117.9 . . ?
C1 C2 H2 117.9 . . ?
N1 C4 C5 122.88(18) . . ?
N1 C4 H4 118.6 . . ?
C5 C4 H4 118.6 . . ?
C4 C5 C6 119.14(18) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C1 119.29(18) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
C8 C7 C15 121.71(17) . . ?
C8 C7 C1 124.00(16) . . ?
C15 C7 C1 114.26(16) . . ?
C7 C8 C9 130.99(17) . . ?
C7 C8 H8 114.5 . . ?
C9 C8 H8 114.5 . . ?
C10 C9 C14 117.88(17) . . ?
C10 C9 C8 116.30(16) . . ?
C14 C9 C8 125.80(17) . . ?
C11 C10 C9 121.63(17) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C12 C11 C10 118.74(17) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C11 C12 C13 121.46(18) . . ?
C11 C12 Cl1 119.84(15) . . ?
C13 C12 Cl1 118.69(15) . . ?
C12 C13 C14 119.30(18) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C13 C14 C9 120.97(18) . . ?
C13 C14 H14 119.5 . . ?
C9 C14 H14 119.5 . . ?
N2 C15 C7 176.6(2) . . ?

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
C4 N1 C2 C1 0.1(3) . . . . ?
C6 C1 C2 N1 -0.5(3) . . . . ?
C7 C1 C2 N1 -179.30(18) . . . . ?
C2 N1 C4 C5 0.2(3) . . . . ?
N1 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 C1 -0.3(3) . . . . ?
C2 C1 C6 C5 0.6(3) . . . . ?
C7 C1 C6 C5 179.38(18) . . . . ?
C6 C1 C7 C8 166.18(19) . . . . ?
C2 C1 C7 C8 -15.1(3) . . . . ?
C6 C1 C7 C15 -15.8(3) . . . . ?
C2 C1 C7 C15 162.92(18) . . . . ?
C15 C7 C8 C9 2.7(3) . . . . ?
C1 C7 C8 C9 -179.43(18) . . . . ?
C7 C8 C9 C10 -176.63(19) . . . . ?
C7 C8 C9 C14 4.4(3) . . . . ?
C14 C9 C10 C11 -0.4(3) . . . . ?
C8 C9 C10 C11 -179.43(18) . . . . ?
C9 C10 C11 C12 -0.5(3) . . . . ?
C10 C11 C12 C13 1.3(3) . . . . ?
C10 C11 C12 Cl1 -179.35(15) . . . . ?
C11 C12 C13 C14 -1.2(3) . . . . ?
Cl1 C12 C13 C14 179.47(15) . . . . ?
C12 C13 C14 C9 0.3(3) . . . . ?
C10 C9 C14 C13 0.5(3) . . . . ?
C8 C9 C14 C13 179.47(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6 N2 0.95 2.86 3.463(3) 122.2 .
C14 H14 N2 0.95 2.57 3.422(3) 149.3 .
C2 H2 N1 0.95 2.59 3.522(2) 166.3 3_567
C8 H8 N1 0.95 2.65 3.572(2) 165.1 3_567
C10 H10 N2 0.95 2.81 3.283(3) 111.8 2_665
C11 H11 N2 0.95 2.66 3.518(3) 150.2 2_765

_refine_diff_density_max         0.209
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.038

_shelxl_version_number           2014-3

