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

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

data_15278a1NNC
_database_code_depnum_ccdc_archive 'CCDC 1491528'
#Added by publCIF



_audit_update_record             
;
2016-07-07 deposited with the CCDC.
2016-08-12 downloaded from the CCDC.
;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '4-chlorobenzaldehyde 2-(2-pyridinyl)hydrazone'
_chemical_name_common            ?
_chemical_melting_point          '471-474 K'
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 Cl N3'
_chemical_formula_weight         231.68

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                   6.4948(13)
_cell_length_b                   8.2220(16)
_cell_length_c                   20.348(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.842(2)
_cell_angle_gamma                90
_cell_volume                     1086.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2977
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      27.37

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   0.7645
_exptl_transmission_factor_max   0.9281
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.324
_shelx_estimated_absorpt_T_min   0.895
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS 2012/1 (Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and σ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12258
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.002
_diffrn_reflns_theta_max         27.467
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2488
_reflns_number_gt                1938
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'PLATON (Spek, 2009) Mercury (Macrae et al., 2008)'
_computing_publication_material  'Bruker SHELXTL'
_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+0.4198P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2488
_refine_ls_number_parameters     148
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.1026
_refine_ls_wR_factor_gt          0.0942
_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
C1 C -0.0330(2) -0.00020(19) 0.39424(8) 0.0274(3) Uani 1 1 d . . . . .
H1 H -0.1297 -0.0856 0.3878 0.033 Uiso 1 1 calc R U . . .
C2 C 0.1553(2) 0.00197(18) 0.35593(7) 0.0252(3) Uani 1 1 d . . . . .
C3 C 0.1795(3) -0.1097(2) 0.30529(8) 0.0329(4) Uani 1 1 d . . . . .
H3 H 0.0756 -0.1889 0.2974 0.039 Uiso 1 1 calc R U . . .
C4 C 0.3517(3) -0.1076(2) 0.26628(8) 0.0360(4) Uani 1 1 d . . . . .
H4 H 0.3665 -0.1842 0.2317 0.043 Uiso 1 1 calc R U . . .
C5 C 0.5013(2) 0.0073(2) 0.27836(8) 0.0302(4) Uani 1 1 d . . . . .
C6 C 0.4860(2) 0.1162(2) 0.32956(8) 0.0295(4) Uani 1 1 d . . . . .
H6 H 0.5928 0.1927 0.3380 0.035 Uiso 1 1 calc R U . . .
C7 C 0.3136(2) 0.11294(19) 0.36851(8) 0.0269(3) Uani 1 1 d . . . . .
H7 H 0.3027 0.1869 0.4042 0.032 Uiso 1 1 calc R U . . .
C8 C -0.2966(2) 0.21831(18) 0.51417(7) 0.0271(3) Uani 1 1 d . . . . .
C9 C -0.5362(3) 0.3227(2) 0.58322(9) 0.0381(4) Uani 1 1 d . . . . .
H9 H -0.6698 0.3177 0.6015 0.046 Uiso 1 1 calc R U . . .
C10 C -0.4085(3) 0.4469(2) 0.60329(9) 0.0426(5) Uani 1 1 d . . . . .
H10 H -0.4526 0.5258 0.6342 0.051 Uiso 1 1 calc R U . . .
C11 C -0.2134(3) 0.4529(2) 0.57690(9) 0.0389(4) Uani 1 1 d . . . . .
H11 H -0.1199 0.5359 0.5901 0.047 Uiso 1 1 calc R U . . .
C12 C -0.1555(3) 0.3393(2) 0.53186(8) 0.0322(4) Uani 1 1 d . . . . .
H12 H -0.0226 0.3425 0.5130 0.039 Uiso 1 1 calc R U . . .
Cl1 Cl 0.71481(7) 0.01691(6) 0.22783(2) 0.04616(16) Uani 1 1 d . . . . .
H2N H -0.328(3) 0.0125(18) 0.4638(11) 0.055 Uiso 1 1 d D U . . .
N1 N -0.06972(19) 0.11041(16) 0.43612(6) 0.0279(3) Uani 1 1 d . . . . .
N2 N -0.2501(2) 0.10037(17) 0.46898(7) 0.0295(3) Uani 1 1 d D . . . .
N3 N -0.4847(2) 0.20813(16) 0.53958(7) 0.0311(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.271(2) . ?
C1 C2 1.460(2) . ?
C1 H1 0.95 . ?
C2 C3 1.391(2) . ?
C2 C7 1.395(2) . ?
C3 C4 1.381(2) . ?
C3 H3 0.95 . ?
C4 C5 1.375(2) . ?
C4 H4 0.95 . ?
C5 C6 1.379(2) . ?
C5 Cl1 1.7403(16) . ?
C6 C7 1.382(2) . ?
C6 H6 0.95 . ?
C7 H7 0.95 . ?
C8 N3 1.336(2) . ?
C8 N2 1.373(2) . ?
C8 C12 1.396(2) . ?
C9 N3 1.340(2) . ?
C9 C10 1.374(2) . ?
C9 H9 0.95 . ?
C10 C11 1.385(2) . ?
C10 H10 0.95 . ?
C11 C12 1.365(2) . ?
C11 H11 0.95 . ?
C12 H12 0.95 . ?
N1 N2 1.3598(17) . ?
N2 H2N 0.888(9) . ?

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
N1 C1 C2 121.05(14) . . ?
N1 C1 H1 119.5 . . ?
C2 C1 H1 119.5 . . ?
C3 C2 C7 118.47(14) . . ?
C3 C2 C1 119.47(14) . . ?
C7 C2 C1 122.05(14) . . ?
C4 C3 C2 121.26(15) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C5 C4 C3 118.80(15) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.54(15) . . ?
C4 C5 Cl1 119.52(13) . . ?
C6 C5 Cl1 118.94(13) . . ?
C5 C6 C7 119.26(15) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C6 C7 C2 120.57(14) . . ?
C6 C7 H7 119.7 . . ?
C2 C7 H7 119.7 . . ?
N3 C8 N2 115.25(13) . . ?
N3 C8 C12 123.03(14) . . ?
N2 C8 C12 121.72(14) . . ?
N3 C9 C10 124.34(16) . . ?
N3 C9 H9 117.8 . . ?
C10 C9 H9 117.8 . . ?
C9 C10 C11 117.58(16) . . ?
C9 C10 H10 121.2 . . ?
C11 C10 H10 121.2 . . ?
C12 C11 C10 119.90(16) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C8 118.34(15) . . ?
C11 C12 H12 120.8 . . ?
C8 C12 H12 120.8 . . ?
C1 N1 N2 117.22(13) . . ?
N1 N2 C8 119.09(13) . . ?
N1 N2 H2N 119.1(15) . . ?
C8 N2 H2N 121.5(16) . . ?
C8 N3 C9 116.80(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
N1 C1 C2 C3 -172.53(15) . . . . ?
N1 C1 C2 C7 7.6(2) . . . . ?
C2 C1 N1 N2 179.08(13) . . . . ?
C1 N1 N2 C8 -179.35(14) . . . . ?
N3 C8 N2 N1 173.86(13) . . . . ?
C12 C8 N2 N1 -6.2(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
N2 H2N N3 0.888(9) 2.184(10) 3.0697(19) 175(2) 3_456

_refine_diff_density_max         0.275
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.046


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# 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_15280a1CNNa
_database_code_depnum_ccdc_archive 'CCDC 1491529'
_audit_update_record             
;
2016-07-07 deposited with the CCDC.
2016-08-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'2-pyridinecarboxaldehyde 2-(4-chlorophenyl)hydrazone'
_chemical_name_common            ?
_chemical_melting_point          '457-460 K'
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 Cl N3'
_chemical_formula_weight         231.68

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       
;
Polymorph I
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                   11.9741(17)
_cell_length_b                   4.5330(7)
_cell_length_c                   20.337(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.807(2)
_cell_angle_gamma                90
_cell_volume                     1101.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2973
_cell_measurement_theta_min      3.36
_cell_measurement_theta_max      27.27

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.320
_shelx_estimated_absorpt_T_min   0.856
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8378
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS 2012/1 (Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10461
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.920
_diffrn_reflns_theta_max         27.298
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2466
_reflns_number_gt                1778
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'PLATON (Spek, 2009) Mercury (Macrae et al., 2008)'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0382P)²+0.2907P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2466
_refine_ls_number_parameters     148
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.0952
_refine_ls_wR_factor_gt          0.0852
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.028
_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
C1 C 0.27999(15) -0.0996(4) 0.82810(8) 0.0262(4) Uani 1 1 d . . . . .
H1 H 0.2689 -0.1055 0.7814 0.031 Uiso 1 1 calc R U . . .
C2 C 0.50600(14) 0.3942(4) 0.83250(8) 0.0236(4) Uani 1 1 d . . . . .
C3 C 0.57589(15) 0.4980(4) 0.78554(8) 0.0266(4) Uani 1 1 d . . . . .
H3 H 0.5640 0.4350 0.7411 0.032 Uiso 1 1 calc R U . . .
C4 C 0.66167(15) 0.6899(4) 0.80245(8) 0.0280(4) Uani 1 1 d . . . . .
H4 H 0.7085 0.7603 0.7699 0.034 Uiso 1 1 calc R U . . .
C5 C 0.67923(15) 0.7796(4) 0.86729(9) 0.0272(4) Uani 1 1 d . . . . .
C6 C 0.61071(15) 0.6799(4) 0.91462(8) 0.0288(4) Uani 1 1 d . . . . .
H6 H 0.6230 0.7446 0.9589 0.035 Uiso 1 1 calc R U . . .
C7 C 0.52455(15) 0.4867(4) 0.89766(8) 0.0272(4) Uani 1 1 d . . . . .
H7 H 0.4780 0.4168 0.9303 0.033 Uiso 1 1 calc R U . . .
C8 C 0.20840(14) -0.2778(4) 0.86709(8) 0.0237(4) Uani 1 1 d . . . . .
C9 C 0.05559(16) -0.5831(4) 0.86552(9) 0.0342(5) Uani 1 1 d . . . . .
H9 H -0.0057 -0.6748 0.8415 0.041 Uiso 1 1 calc R U . . .
C10 C 0.06995(16) -0.6369(4) 0.93184(9) 0.0340(5) Uani 1 1 d . . . . .
H10 H 0.0210 -0.7656 0.9530 0.041 Uiso 1 1 calc R U . . .
C11 C 0.15767(16) -0.4987(4) 0.96716(9) 0.0325(4) Uani 1 1 d . . . . .
H11 H 0.1694 -0.5289 1.0133 0.039 Uiso 1 1 calc R U . . .
C12 C 0.22777(15) -0.3173(4) 0.93475(8) 0.0284(4) Uani 1 1 d . . . . .
H12 H 0.2885 -0.2204 0.9582 0.034 Uiso 1 1 calc R U . . .
Cl1 Cl 0.78988(4) 1.01692(11) 0.88898(2) 0.03843(16) Uani 1 1 d . . . . .
H2N H 0.4102(17) 0.167(5) 0.7696(5) 0.046 Uiso 1 1 d D U . . .
N1 N 0.35750(12) 0.0651(3) 0.85434(7) 0.0252(3) Uani 1 1 d . . . . .
N2 N 0.42049(13) 0.2070(4) 0.81161(7) 0.0288(4) Uani 1 1 d D . . . .
N3 N 0.12266(13) -0.4093(3) 0.83263(7) 0.0285(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
C1 N1 1.280(2) . ?
C1 C8 1.451(2) . ?
C1 H1 0.95 . ?
C2 N2 1.375(2) . ?
C2 C3 1.393(2) . ?
C2 C7 1.394(2) . ?
C3 C4 1.372(2) . ?
C3 H3 0.95 . ?
C4 C5 1.383(2) . ?
C4 H4 0.95 . ?
C5 C6 1.382(2) . ?
C5 Cl1 1.7405(18) . ?
C6 C7 1.380(2) . ?
C6 H6 0.95 . ?
C7 H7 0.95 . ?
C8 N3 1.343(2) . ?
C8 C12 1.392(2) . ?
C9 N3 1.336(2) . ?
C9 C10 1.370(3) . ?
C9 H9 0.95 . ?
C10 C11 1.382(3) . ?
C10 H10 0.95 . ?
C11 C12 1.374(3) . ?
C11 H11 0.95 . ?
C12 H12 0.95 . ?
N1 N2 1.351(2) . ?
N2 H2N 0.874(9) . ?

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
N1 C1 C8 122.36(15) . . ?
N1 C1 H1 118.8 . . ?
C8 C1 H1 118.8 . . ?
N2 C2 C3 117.75(15) . . ?
N2 C2 C7 123.21(16) . . ?
C3 C2 C7 119.03(16) . . ?
C4 C3 C2 121.07(16) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 119.30(16) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 120.56(17) . . ?
C6 C5 Cl1 120.20(14) . . ?
C4 C5 Cl1 119.24(14) . . ?
C7 C6 C5 120.16(16) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C2 119.87(16) . . ?
C6 C7 H7 120.1 . . ?
C2 C7 H7 120.1 . . ?
N3 C8 C12 122.02(16) . . ?
N3 C8 C1 114.87(15) . . ?
C12 C8 C1 123.10(16) . . ?
N3 C9 C10 123.89(18) . . ?
N3 C9 H9 118.1 . . ?
C10 C9 H9 118.1 . . ?
C9 C10 C11 118.17(17) . . ?
C9 C10 H10 120.9 . . ?
C11 C10 H10 120.9 . . ?
C12 C11 C10 119.28(17) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C11 C12 C8 118.96(17) . . ?
C11 C12 H12 120.5 . . ?
C8 C12 H12 120.5 . . ?
C1 N1 N2 115.47(14) . . ?
N1 N2 C2 122.08(14) . . ?
N1 N2 H2N 118.7(15) . . ?
C2 N2 H2N 119.0(14) . . ?
C9 N3 C8 117.67(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C8 N3 172.13(16) . . . . ?
N1 C1 C8 C12 -9.4(3) . . . . ?
C8 C1 N1 N2 177.03(15) . . . . ?
C1 N1 N2 C2 179.23(16) . . . . ?
C3 C2 N2 N1 171.31(16) . . . . ?
C7 C2 N2 N1 -9.6(3) . . . . ?


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
N2 H2N N3 0.874(9) 2.119(10) 2.991(2) 176(2) 2_556

_refine_diff_density_max         0.208
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.048


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# 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_16008a1CNNb
_database_code_depnum_ccdc_archive 'CCDC 1491530'
_audit_update_record             
;
2016-07-07 deposited with the CCDC.
2016-08-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
2pyridinecarboxaldehyde2(4chlorophenyl)hydrazone
_chemical_name_common            ?
_chemical_melting_point          '457-460 K'
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 Cl N3'
_chemical_formula_weight         231.68

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      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       
;
Polymorph II
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                   29.3899(18)
_cell_length_b                   3.8643(3)
_cell_length_c                   20.0344(13)
_cell_angle_alpha                90
_cell_angle_beta                 108.118(5)
_cell_angle_gamma                90
_cell_volume                     2162.5(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    2974
_cell_measurement_theta_min      3.16
_cell_measurement_theta_max      74.39

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    2.902
_shelx_estimated_absorpt_T_min   0.595
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5476
_exptl_absorpt_correction_T_max  0.6566
_exptl_absorpt_process_details   'SADABS-2014 (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'ImuS micro-focus'
_diffrn_measurement_device_type  'Bruker-AXS D8 Venture PHOTON-II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24609
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_av_R_equivalents  0.0681
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.164
_diffrn_reflns_theta_max         74.741
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4410
_reflns_number_gt                3376
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'PLATON (Spek 2009) Mercury (Macrae et al. 2008)'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0419P)²+3.8450P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4410
_refine_ls_number_parameters     297
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0652
_refine_ls_wR_factor_ref         0.1456
_refine_ls_wR_factor_gt          0.1341
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.73956(10) 1.0560(9) 0.54268(14) 0.0221(6) Uani 1 1 d . . . . .
H1 H 0.7416 1.0485 0.5909 0.026 Uiso 1 1 calc R U . . .
C2 C 0.62277(9) 0.7171(9) 0.47620(14) 0.0217(6) Uani 1 1 d . . . . .
C3 C 0.59225(10) 0.5347(9) 0.50453(15) 0.0235(7) Uani 1 1 d . . . . .
H3 H 0.6027 0.4753 0.5529 0.028 Uiso 1 1 calc R U . . .
C4 C 0.54698(10) 0.4389(9) 0.46309(16) 0.0246(7) Uani 1 1 d . . . . .
H4 H 0.5264 0.3146 0.4828 0.030 Uiso 1 1 calc R U . . .
C5 C 0.53205(10) 0.5256(9) 0.39296(15) 0.0246(7) Uani 1 1 d . . . . .
C6 C 0.56201(10) 0.7033(9) 0.36284(15) 0.0254(7) Uani 1 1 d . . . . .
H6 H 0.5514 0.7592 0.3143 0.030 Uiso 1 1 calc R U . . .
C7 C 0.60757(10) 0.7979(9) 0.40469(14) 0.0233(7) Uani 1 1 d . . . . .
H7 H 0.6284 0.9177 0.3847 0.028 Uiso 1 1 calc R U . . .
C8 C 0.77989(10) 1.1889(9) 0.52307(14) 0.0220(6) Uani 1 1 d . . . . .
C9 C 0.85506(10) 1.4321(9) 0.56060(15) 0.0264(7) Uani 1 1 d . . . . .
H9 H 0.8809 1.5246 0.5976 0.032 Uiso 1 1 calc R U . . .
C10 C 0.85922(10) 1.4263(9) 0.49357(16) 0.0277(7) Uani 1 1 d . . . . .
H10 H 0.8874 1.5080 0.4851 0.033 Uiso 1 1 calc R U . . .
C11 C 0.82116(10) 1.2982(9) 0.43917(15) 0.0271(7) Uani 1 1 d . . . . .
H11 H 0.8227 1.2914 0.3925 0.032 Uiso 1 1 calc R U . . .
C12 C 0.78111(10) 1.1808(8) 0.45417(14) 0.0223(6) Uani 1 1 d . . . . .
H12 H 0.7545 1.0949 0.4176 0.027 Uiso 1 1 calc R U . . .
C13 C 0.75590(10) 0.6230(9) 0.70947(14) 0.0243(7) Uani 1 1 d . . . . .
H13 H 0.7506 0.5346 0.6634 0.029 Uiso 1 1 calc R U . . .
C14 C 0.87945(10) 0.4458(9) 0.77666(15) 0.0231(6) Uani 1 1 d . . . . .
C15 C 0.91397(10) 0.2887(9) 0.75209(15) 0.0248(7) Uani 1 1 d . . . . .
H15 H 0.9047 0.1830 0.7070 0.030 Uiso 1 1 calc R U . . .
C16 C 0.96157(11) 0.2863(9) 0.79307(16) 0.0261(7) Uani 1 1 d . . . . .
H16 H 0.9851 0.1814 0.7763 0.031 Uiso 1 1 calc R U . . .
C17 C 0.97433(10) 0.4383(9) 0.85870(15) 0.0254(7) Uani 1 1 d . . . . .
C18 C 0.94062(10) 0.5908(9) 0.88475(15) 0.0264(7) Uani 1 1 d . . . . .
H18 H 0.9500 0.6923 0.9302 0.032 Uiso 1 1 calc R U . . .
C19 C 0.89301(10) 0.5928(9) 0.84346(14) 0.0236(7) Uani 1 1 d . . . . .
H19 H 0.8695 0.6949 0.8608 0.028 Uiso 1 1 calc R U . . .
C20 C 0.71632(10) 0.7826(9) 0.72783(14) 0.0212(6) Uani 1 1 d . . . . .
C21 C 0.63830(10) 0.9708(9) 0.68743(15) 0.0279(7) Uani 1 1 d . . . . .
H21 H 0.6098 1.0056 0.6495 0.033 Uiso 1 1 calc R U . . .
C22 C 0.63828(10) 1.0676(9) 0.75391(16) 0.0279(7) Uani 1 1 d . . . . .
H22 H 0.6106 1.1647 0.7614 0.033 Uiso 1 1 calc R U . . .
C23 C 0.67991(10) 1.0186(9) 0.80920(15) 0.0257(7) Uani 1 1 d . . . . .
H23 H 0.6812 1.0809 0.8556 0.031 Uiso 1 1 calc R U . . .
C24 C 0.71953(10) 0.8781(9) 0.79623(15) 0.0243(7) Uani 1 1 d . . . . .
H24 H 0.7486 0.8470 0.8334 0.029 Uiso 1 1 calc R U . . .
Cl1 Cl 0.47460(3) 0.4101(3) 0.34063(4) 0.0363(2) Uani 1 1 d . . . . .
Cl2 Cl 1.03481(3) 0.4493(3) 0.90913(4) 0.0383(2) Uani 1 1 d . . . . .
H2N H 0.6744(12) 0.798(10) 0.5668(6) 0.035(10) Uiso 1 1 d D . . . .
H5N H 0.8268(10) 0.379(8) 0.6897(8) 0.020(8) Uiso 1 1 d D . . . .
N1 N 0.70117(8) 0.9483(7) 0.49635(12) 0.0227(6) Uani 1 1 d . . . . .
N2 N 0.66717(8) 0.8170(8) 0.52112(12) 0.0249(6) Uani 1 1 d D . . . .
N3 N 0.81665(8) 1.3143(7) 0.57623(12) 0.0242(6) Uani 1 1 d . . . . .
N4 N 0.79783(8) 0.6005(8) 0.75469(12) 0.0248(6) Uani 1 1 d . . . . .
N5 N 0.83204(9) 0.4515(8) 0.73280(12) 0.0268(6) Uani 1 1 d D . . . .
N6 N 0.67585(8) 0.8314(7) 0.67327(12) 0.0241(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.287(4) . ?
C1 C8 1.453(4) . ?
C1 H1 0.95 . ?
C2 N2 1.390(4) . ?
C2 C3 1.393(4) . ?
C2 C7 1.397(4) . ?
C3 C4 1.382(4) . ?
C3 H3 0.95 . ?
C4 C5 1.377(4) . ?
C4 H4 0.95 . ?
C5 C6 1.393(4) . ?
C5 Cl1 1.746(3) . ?
C6 C7 1.390(4) . ?
C6 H6 0.95 . ?
C7 H7 0.95 . ?
C8 N3 1.349(4) . ?
C8 C12 1.392(4) . ?
C9 N3 1.342(4) . ?
C9 C10 1.386(4) . ?
C9 H9 0.95 . ?
C10 C11 1.388(4) . ?
C10 H10 0.95 . ?
C11 C12 1.379(4) . ?
C11 H11 0.95 . ?
C12 H12 0.95 . ?
C13 N4 1.286(4) . ?
C13 C20 1.461(4) . ?
C13 H13 0.95 . ?
C14 C19 1.393(4) . ?
C14 C15 1.397(4) . ?
C14 N5 1.397(4) . ?
C15 C16 1.384(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.381(4) . ?
C16 H16 0.95 . ?
C17 C18 1.386(4) . ?
C17 Cl2 1.751(3) . ?
C18 C19 1.387(4) . ?
C18 H18 0.95 . ?
C19 H19 0.95 . ?
C20 N6 1.355(3) . ?
C20 C24 1.394(4) . ?
C21 N6 1.335(4) . ?
C21 C22 1.384(4) . ?
C21 H21 0.95 . ?
C22 C23 1.385(4) . ?
C22 H22 0.95 . ?
C23 C24 1.381(4) . ?
C23 H23 0.95 . ?
C24 H24 0.95 . ?
N1 N2 1.346(3) . ?
N2 H2N 0.876(10) . ?
N4 N5 1.345(3) . ?
N5 H5N 0.875(10) . ?

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
N1 C1 C8 121.7(2) . . ?
N1 C1 H1 119.2 . . ?
C8 C1 H1 119.2 . . ?
N2 C2 C3 118.1(3) . . ?
N2 C2 C7 122.6(3) . . ?
C3 C2 C7 119.3(3) . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C4 C3 119.3(3) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 121.2(3) . . ?
C4 C5 Cl1 119.5(2) . . ?
C6 C5 Cl1 119.3(2) . . ?
C7 C6 C5 119.2(3) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C6 C7 C2 120.0(3) . . ?
C6 C7 H7 120.0 . . ?
C2 C7 H7 120.0 . . ?
N3 C8 C12 122.0(3) . . ?
N3 C8 C1 115.7(2) . . ?
C12 C8 C1 122.3(3) . . ?
N3 C9 C10 123.7(3) . . ?
N3 C9 H9 118.1 . . ?
C10 C9 H9 118.1 . . ?
C9 C10 C11 118.3(3) . . ?
C9 C10 H10 120.8 . . ?
C11 C10 H10 120.8 . . ?
C12 C11 C10 118.7(3) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C11 C12 C8 119.7(3) . . ?
C11 C12 H12 120.1 . . ?
C8 C12 H12 120.1 . . ?
N4 C13 C20 121.0(3) . . ?
N4 C13 H13 119.5 . . ?
C20 C13 H13 119.5 . . ?
C19 C14 C15 119.6(3) . . ?
C19 C14 N5 122.0(3) . . ?
C15 C14 N5 118.5(3) . . ?
C16 C15 C14 120.3(3) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C17 C16 C15 119.1(3) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C16 C17 C18 121.6(3) . . ?
C16 C17 Cl2 119.1(2) . . ?
C18 C17 Cl2 119.3(2) . . ?
C17 C18 C19 119.0(3) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
C18 C19 C14 120.3(3) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?
N6 C20 C24 122.0(3) . . ?
N6 C20 C13 115.1(2) . . ?
C24 C20 C13 122.9(3) . . ?
N6 C21 C22 124.1(3) . . ?
N6 C21 H21 117.9 . . ?
C22 C21 H21 117.9 . . ?
C21 C22 C23 117.9(3) . . ?
C21 C22 H22 121.0 . . ?
C23 C22 H22 121.0 . . ?
C24 C23 C22 119.4(3) . . ?
C24 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
C23 C24 C20 119.1(3) . . ?
C23 C24 H24 120.5 . . ?
C20 C24 H24 120.5 . . ?
C1 N1 N2 116.2(2) . . ?
N1 N2 C2 121.4(2) . . ?
N1 N2 H2N 117(2) . . ?
C2 N2 H2N 122(2) . . ?
C9 N3 C8 117.6(2) . . ?
C13 N4 N5 116.7(2) . . ?
N4 N5 C14 120.1(2) . . ?
N4 N5 H5N 123(2) . . ?
C14 N5 H5N 117(2) . . ?
C21 N6 C20 117.4(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

N1 C1 C8 N3 175.8(3) . . . . ?
N1 C1 C8 C12 -5.5(5) . . . . ?
N4 C13 C20 N6 171.7(3) . . . . ?
N4 C13 C20 C24 -8.4(5) . . . . ?
C8 C1 N1 N2 177.1(3) . . . . ?
C1 N1 N2 C2 175.0(3) . . . . ?
C3 C2 N2 N1 170.2(3) . . . . ?
C7 C2 N2 N1 -11.0(5) . . . . ?
C20 C13 N4 N5 -179.6(3) . . . . ?
C13 N4 N5 C14 174.1(3) . . . . ?
C19 C14 N5 N4 -0.3(5) . . . . ?
C15 C14 N5 N4 180.0(3) . . . . ?

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
N2 H2N N6 0.876(10) 2.123(14) 2.979(3) 165(3) .
N5 H5N N3 0.875(10) 2.213(13) 3.073(3) 167(3) 1_545

_refine_diff_density_max         0.571
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.140


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# 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_16009a2CNN
_database_code_depnum_ccdc_archive 'CCDC 1491531'
_audit_update_record             
;
2016-07-07 deposited with the CCDC.
2016-08-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
2pyridinecarboxaldehyde2(4bromophenyl)hydrazone
_chemical_name_common            ?
_chemical_melting_point          '466-470 K'
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 Br N3'
_chemical_formula_weight         276.14

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                   16.787(4)
_cell_length_b                   3.9475(9)
_cell_length_c                   17.596(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.296(16)
_cell_angle_gamma                90
_cell_volume                     1107.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    2940
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      74.56

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    4.843
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5190
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_process_details   'SADABS-2014 (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'ImuS micro-focus'
_diffrn_measurement_device_type  'Bruker-AXS D8 Venture PHOTON-II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11623
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.175
_diffrn_reflns_theta_max         74.620
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2243
_reflns_number_gt                2178
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'PLATON (Spek 2009) Mercury (Macrae et al. 2008)'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0253P)²+0.6459P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2243
_refine_ls_number_parameters     148
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0228
_refine_ls_R_factor_gt           0.0222
_refine_ls_wR_factor_ref         0.0567
_refine_ls_wR_factor_gt          0.0556
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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
Br1 Br 0.11635(2) -0.07022(5) 0.67161(2) 0.02723(8) Uani 1 1 d . . . . .
C1 C 0.32207(9) 0.5901(4) 0.33679(9) 0.0191(3) Uani 1 1 d . . . . .
H1 H 0.2795 0.5504 0.2873 0.023 Uiso 1 1 calc R U . . .
C2 C 0.21047(8) 0.2616(4) 0.45960(8) 0.0180(3) Uani 1 1 d . . . . .
C3 C 0.13687(9) 0.0718(4) 0.44548(9) 0.0200(3) Uani 1 1 d . . . . .
H3 H 0.1056 0.0108 0.3923 0.024 Uiso 1 1 calc R U . . .
C4 C 0.10922(9) -0.0278(4) 0.50836(10) 0.0212(3) Uani 1 1 d . . . . .
H4 H 0.0595 -0.1586 0.4987 0.025 Uiso 1 1 calc R U . . .
C5 C 0.15513(10) 0.0660(4) 0.58570(9) 0.0204(3) Uani 1 1 d . . . . .
C6 C 0.22831(9) 0.2538(4) 0.60112(9) 0.0213(3) Uani 1 1 d . . . . .
H6 H 0.2591 0.3153 0.6545 0.026 Uiso 1 1 calc R U . . .
C7 C 0.25623(9) 0.3514(4) 0.53790(9) 0.0193(3) Uani 1 1 d . . . . .
H7 H 0.3064 0.4792 0.5480 0.023 Uiso 1 1 calc R U . . .
C8 C 0.40052(9) 0.7466(4) 0.33620(8) 0.0175(3) Uani 1 1 d . . . . .
C9 C 0.47455(9) 0.9796(5) 0.25881(9) 0.0220(3) Uani 1 1 d . . . . .
H9 H 0.4768 1.0454 0.2076 0.026 Uiso 1 1 calc R U . . .
C10 C 0.54475(10) 1.0359(4) 0.32449(10) 0.0233(3) Uani 1 1 d . . . . .
H10 H 0.5940 1.1345 0.3185 0.028 Uiso 1 1 calc R U . . .
C11 C 0.54085(9) 0.9437(4) 0.39945(9) 0.0224(3) Uani 1 1 d . . . . .
H11 H 0.5875 0.9810 0.4459 0.027 Uiso 1 1 calc R U . . .
C12 C 0.46838(9) 0.7973(4) 0.40572(8) 0.0197(3) Uani 1 1 d . . . . .
H12 H 0.4647 0.7320 0.4565 0.024 Uiso 1 1 calc R U . . .
H2N H 0.1983(10) 0.326(6) 0.3457(7) 0.024 Uiso 1 1 d D U . . .
N1 N 0.30866(7) 0.5040(4) 0.40226(7) 0.0187(2) Uani 1 1 d . . . . .
N2 N 0.23375(7) 0.3560(4) 0.39369(7) 0.0204(3) Uani 1 1 d D . . . .
N3 N 0.40349(7) 0.8373(4) 0.26334(7) 0.0197(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
Br1 C5 1.9016(15) . ?
C1 N1 1.287(2) . ?
C1 C8 1.458(2) . ?
C1 H1 0.95 . ?
C2 N2 1.3861(19) . ?
C2 C7 1.396(2) . ?
C2 C3 1.399(2) . ?
C3 C4 1.385(2) . ?
C3 H3 0.95 . ?
C4 C5 1.387(2) . ?
C4 H4 0.95 . ?
C5 C6 1.387(2) . ?
C6 C7 1.390(2) . ?
C6 H6 0.95 . ?
C7 H7 0.95 . ?
C8 N3 1.3470(19) . ?
C8 C12 1.400(2) . ?
C9 N3 1.343(2) . ?
C9 C10 1.385(2) . ?
C9 H9 0.95 . ?
C10 C11 1.390(2) . ?
C10 H10 0.95 . ?
C11 C12 1.382(2) . ?
C11 H11 0.95 . ?
C12 H12 0.95 . ?
N1 N2 1.3513(18) . ?
N2 H2N 0.875(9) . ?

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
N1 C1 C8 122.05(13) . . ?
N1 C1 H1 119.0 . . ?
C8 C1 H1 119.0 . . ?
N2 C2 C7 123.02(13) . . ?
N2 C2 C3 117.44(13) . . ?
C7 C2 C3 119.53(13) . . ?
C4 C3 C2 120.62(14) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.05(14) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 121.33(14) . . ?
C6 C5 Br1 119.93(12) . . ?
C4 C5 Br1 118.74(12) . . ?
C5 C6 C7 119.47(14) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C6 C7 C2 120.00(14) . . ?
C6 C7 H7 120.0 . . ?
C2 C7 H7 120.0 . . ?
N3 C8 C12 122.04(14) . . ?
N3 C8 C1 115.03(13) . . ?
C12 C8 C1 122.93(13) . . ?
N3 C9 C10 123.80(14) . . ?
N3 C9 H9 118.1 . . ?
C10 C9 H9 118.1 . . ?
C9 C10 C11 117.95(14) . . ?
C9 C10 H10 121.0 . . ?
C11 C10 H10 121.0 . . ?
C12 C11 C10 119.35(14) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C8 119.04(13) . . ?
C11 C12 H12 120.5 . . ?
C8 C12 H12 120.5 . . ?
C1 N1 N2 115.62(12) . . ?
N1 N2 C2 121.33(12) . . ?
N1 N2 H2N 119.6(13) . . ?
C2 N2 H2N 119.0(13) . . ?
C9 N3 C8 117.82(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

N1 C1 C8 N3 -176.86(15) . . . . ?
N1 C1 C8 C12 3.7(2) . . . . ?
C8 C1 N1 N2 -178.86(14) . . . . ?
C1 N1 N2 C2 -177.85(14) . . . . ?
C7 C2 N2 N1 8.9(2) . . . . ?
C3 C2 N2 N1 -172.03(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
N2 H2N N3 0.875(9) 2.132(10) 2.9919(18) 167.5(19) 2_545

_refine_diff_density_max         0.316
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.065


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# 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_15283a3NNC
_database_code_depnum_ccdc_archive 'CCDC 1491532'
_audit_update_record             
;
2016-07-07 deposited with the CCDC.
2016-08-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        2-pyrcarboxaldehyde-2-(4-CNphenyl)hydrazone
_chemical_name_common            ?
_chemical_melting_point          511-516K
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H10 N4'
_chemical_formula_weight         222.25

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'

_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                   17.0570(7)
_cell_length_b                   3.8670(2)
_cell_length_c                   18.2283(7)
_cell_angle_alpha                90
_cell_angle_beta                 115.093(2)
_cell_angle_gamma                90
_cell_volume                     1088.85(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    2926
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      74.21

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.686
_shelx_estimated_absorpt_T_min   0.847
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7525
_exptl_absorpt_correction_T_max  0.9288
_exptl_absorpt_process_details   'SADABS-2014 (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'ImuS micro-focus'
_diffrn_measurement_device_type  'Bruker-AXS D8 Venture PHOTON-II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11971
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.861
_diffrn_reflns_theta_max         74.527
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2216
_reflns_number_gt                1677
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'PLATON (Spek 2009) Mercury (Macrae et al. 2008)'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1281P)²+1.7150P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2216
_refine_ls_number_parameters     157
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0995
_refine_ls_R_factor_gt           0.0798
_refine_ls_wR_factor_ref         0.2489
_refine_ls_wR_factor_gt          0.2227
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.29731(17) 0.7810(8) 0.33477(15) 0.0266(7) Uani 1 1 d . . . . .
H1 H 0.2951 0.6596 0.3792 0.032 Uiso 1 1 calc R U . . .
C2 C 0.21642(17) 0.8901(8) 0.26819(15) 0.0252(6) Uani 1 1 d . . . . .
C3 C 0.13851(17) 0.8166(8) 0.27213(16) 0.0261(6) Uani 1 1 d . . . . .
H3 H 0.1388 0.6989 0.3180 0.031 Uiso 1 1 calc R U . . .
C4 C 0.06041(18) 0.9137(8) 0.20973(16) 0.0275(7) Uani 1 1 d . . . . .
H4 H 0.0074 0.8615 0.2127 0.033 Uiso 1 1 calc R U . . .
C5 C 0.06009(17) 1.0891(8) 0.14237(15) 0.0270(7) Uani 1 1 d . . . . .
C6 C 0.13790(18) 1.1631(8) 0.13767(15) 0.0276(7) Uani 1 1 d . . . . .
H6 H 0.1377 1.2810 0.0919 0.033 Uiso 1 1 calc R U . . .
C7 C 0.21522(18) 1.0637(8) 0.20003(15) 0.0264(6) Uani 1 1 d . . . . .
H7 H 0.2682 1.1133 0.1968 0.032 Uiso 1 1 calc R U . . .
C8 C 0.52375(18) 0.8119(8) 0.40735(17) 0.0295(7) Uani 1 1 d . . . . .
C9 C 0.6705(2) 0.7950(9) 0.48342(17) 0.0348(8) Uani 1 1 d . . . . .
H9 H 0.7182 0.7242 0.5316 0.042 Uiso 1 1 calc R U . . .
C10 C 0.68742(18) 0.9749(8) 0.42630(16) 0.0296(7) Uani 1 1 d . . . . .
H10 H 0.7449 1.0315 0.4349 0.036 Uiso 1 1 calc R U . . .
C11 C 0.61644(19) 1.0693(8) 0.35563(16) 0.0302(7) Uani 1 1 d . . . . .
H11 H 0.6251 1.1872 0.3139 0.036 Uiso 1 1 calc R U . . .
C12 C 0.53488(19) 0.9939(9) 0.34589(17) 0.0326(7) Uani 1 1 d . . . . .
H12 H 0.4862 1.0632 0.2983 0.039 Uiso 1 1 calc R U . . .
C13 C -0.02194(19) 1.2001(8) 0.07951(17) 0.0310(7) Uani 1 1 d . . . . .
H2N H 0.429(2) 0.632(9) 0.4368(15) 0.037 Uiso 1 1 d D U . . .
N1 N 0.37111(16) 0.8443(7) 0.33496(14) 0.0327(7) Uani 1 1 d . . . . .
N2 N 0.44183(16) 0.7308(8) 0.39955(14) 0.0352(7) Uani 1 1 d D . . . .
N3 N 0.59027(17) 0.7139(7) 0.47502(14) 0.0319(6) Uani 1 1 d . . . . .
N4 N -0.08716(17) 1.2947(8) 0.03243(15) 0.0403(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.281(4) . ?
C1 C2 1.461(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.390(4) . ?
C2 C7 1.405(4) . ?
C3 C4 1.387(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.401(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.395(4) . ?
C5 C13 1.448(4) . ?
C6 C7 1.381(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 N3 1.329(4) . ?
C8 N2 1.379(4) . ?
C8 C12 1.402(4) . ?
C9 N3 1.347(4) . ?
C9 C10 1.381(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.391(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.357(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 N4 1.139(4) . ?
N1 N2 1.353(3) . ?
N2 H2N 0.884(5) . ?

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
N1 C1 C2 121.9(3) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C3 C2 C7 119.2(2) . . ?
C3 C2 C1 119.0(2) . . ?
C7 C2 C1 121.8(3) . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.7(3) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 120.2(2) . . ?
C6 C5 C13 121.1(3) . . ?
C4 C5 C13 118.7(3) . . ?
C7 C6 C5 119.6(2) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C6 C7 C2 120.8(3) . . ?
C6 C7 H7 119.6 . . ?
C2 C7 H7 119.6 . . ?
N3 C8 N2 117.4(3) . . ?
N3 C8 C12 122.2(3) . . ?
N2 C8 C12 120.4(3) . . ?
N3 C9 C10 124.0(3) . . ?
N3 C9 H9 118.0 . . ?
C10 C9 H9 118.0 . . ?
C9 C10 C11 116.9(3) . . ?
C9 C10 H10 121.6 . . ?
C11 C10 H10 121.6 . . ?
C12 C11 C10 120.4(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C8 118.8(3) . . ?
C11 C12 H12 120.6 . . ?
C8 C12 H12 120.6 . . ?
N4 C13 C5 177.2(3) . . ?
C1 N1 N2 116.9(2) . . ?
N1 N2 C8 120.4(3) . . ?
N1 N2 H2N 113(2) . . ?
C8 N2 H2N 126(2) . . ?
C8 N3 C9 117.7(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
N1 C1 C2 C3 -179.3(3) . . . . ?
N1 C1 C2 C7 1.4(5) . . . . ?
C2 C1 N1 N2 -179.8(3) . . . . ?
C1 N1 N2 C8 -175.0(3) . . . . ?
N3 C8 N2 N1 175.2(3) . . . . ?
C12 C8 N2 N1 -4.1(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
N2 H2N N3 0.884(5) 2.220(10) 3.090(4) 168(3) 3_666

_refine_diff_density_max         1.115
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.082


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# 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_16020a3CNN
_database_code_depnum_ccdc_archive 'CCDC 1491533'
_audit_update_record             
;
2016-07-07 deposited with the CCDC.
2016-08-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'2pyridinecarboxaldehyde 2(4-cyanophenyl)hydrazone'
_chemical_name_common            ?
_chemical_melting_point          '508-514 K'
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H10 N4'
_chemical_formula_weight         222.25

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'

_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                   13.1678(11)
_cell_length_b                   4.2065(4)
_cell_length_c                   20.2522(18)
_cell_angle_alpha                90
_cell_angle_beta                 93.427(4)
_cell_angle_gamma                90
_cell_volume                     1119.77(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    2898
_cell_measurement_theta_min      3.90
_cell_measurement_theta_max      74.42

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.667
_shelx_estimated_absorpt_T_min   0.851
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5884
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_process_details   'SADABS-2014 (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'ImuS micro-focus'
_diffrn_measurement_device_type  'Bruker-AXS D8 Venture PHOTON-II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15130
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.900
_diffrn_reflns_theta_max         74.519
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2296
_reflns_number_gt                2091
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'PLATON (Spek 2009) Mercury (Macrae et al. 2008)'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0691P)²+0.2415P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2296
_refine_ls_number_parameters     158
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.1250
_refine_ls_wR_factor_gt          0.1193
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_restrained_S_all      1.135
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.28416(9) 0.6185(3) 0.32805(6) 0.0260(3) Uani 1 1 d . . . . .
H1 H 0.2734 0.6304 0.2813 0.031 Uiso 1 1 calc R U . . .
C2 C 0.50202(9) 0.1402(3) 0.32652(6) 0.0254(3) Uani 1 1 d . . . . .
C3 C 0.56425(9) 0.0371(3) 0.27689(6) 0.0273(3) Uani 1 1 d . . . . .
H3 H 0.5475 0.0926 0.2321 0.033 Uiso 1 1 calc R U . . .
C4 C 0.64927(9) -0.1434(3) 0.29254(6) 0.0270(3) Uani 1 1 d . . . . .
H4 H 0.6907 -0.2129 0.2585 0.032 Uiso 1 1 calc R U . . .
C5 C 0.67516(9) -0.2255(3) 0.35847(6) 0.0269(3) Uani 1 1 d . . . . .
C6 C 0.61269(9) -0.1243(3) 0.40809(6) 0.0288(3) Uani 1 1 d . . . . .
H6 H 0.6296 -0.1803 0.4529 0.035 Uiso 1 1 calc R U . . .
C7 C 0.52695(9) 0.0557(3) 0.39259(6) 0.0282(3) Uani 1 1 d . . . . .
H7 H 0.4849 0.1222 0.4265 0.034 Uiso 1 1 calc R U . . .
C8 C 0.21431(8) 0.7858(3) 0.36910(6) 0.0245(3) Uani 1 1 d . . . . .
C9 C 0.06580(9) 1.0743(3) 0.36989(6) 0.0306(3) Uani 1 1 d . . . . .
H9 H 0.0080 1.1637 0.3465 0.037 Uiso 1 1 calc R U . . .
C10 C 0.07630(10) 1.1167(3) 0.43769(6) 0.0321(3) Uani 1 1 d . . . . .
H10 H 0.0276 1.2353 0.4601 0.038 Uiso 1 1 calc R U . . .
C11 C 0.15968(10) 0.9818(3) 0.47203(6) 0.0328(3) Uani 1 1 d . . . . .
H11 H 0.1686 1.0042 0.5187 0.039 Uiso 1 1 calc R U . . .
C12 C 0.22979(9) 0.8144(3) 0.43767(6) 0.0291(3) Uani 1 1 d . . . . .
H12 H 0.2875 0.7203 0.4603 0.035 Uiso 1 1 calc R U . . .
C13 C 0.76589(10) -0.4052(3) 0.37404(6) 0.0302(3) Uani 1 1 d . . . . .
H2N H 0.4020(13) 0.362(4) 0.2654(5) 0.046(5) Uiso 1 1 d D . . . .
N1 N 0.35966(7) 0.4557(2) 0.35272(5) 0.0261(3) Uani 1 1 d . . . . .
N2 N 0.41841(8) 0.3195(3) 0.30748(5) 0.0279(3) Uani 1 1 d D . . . .
N3 N 0.13288(7) 0.9138(3) 0.33550(5) 0.0277(3) Uani 1 1 d . . . . .
N4 N 0.83977(9) -0.5461(3) 0.38531(6) 0.0399(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.2836(15) . ?
C1 C8 1.4575(16) . ?
C1 H1 0.95 . ?
C2 N2 1.3707(16) . ?
C2 C3 1.4029(17) . ?
C2 C7 1.4043(16) . ?
C3 C4 1.3741(17) . ?
C3 H3 0.95 . ?
C4 C5 1.4015(17) . ?
C4 H4 0.95 . ?
C5 C6 1.4023(17) . ?
C5 C13 1.4329(17) . ?
C6 C7 1.3798(17) . ?
C6 H6 0.95 . ?
C7 H7 0.95 . ?
C8 N3 1.3472(15) . ?
C8 C12 1.3966(16) . ?
C9 N3 1.3397(16) . ?
C9 C10 1.3833(18) . ?
C9 H9 0.95 . ?
C10 C11 1.3856(18) . ?
C10 H10 0.95 . ?
C11 C12 1.3818(18) . ?
C11 H11 0.95 . ?
C12 H12 0.95 . ?
C13 N4 1.1502(17) . ?
N1 N2 1.3605(14) . ?
N2 H2N 0.885(9) . ?

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
N1 C1 C8 122.42(10) . . ?
N1 C1 H1 118.8 . . ?
C8 C1 H1 118.8 . . ?
N2 C2 C3 117.53(10) . . ?
N2 C2 C7 123.06(11) . . ?
C3 C2 C7 119.41(11) . . ?
C4 C3 C2 120.55(11) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 120.28(11) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 119.23(11) . . ?
C4 C5 C13 119.45(11) . . ?
C6 C5 C13 121.30(10) . . ?
C7 C6 C5 120.70(11) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C2 119.82(11) . . ?
C6 C7 H7 120.1 . . ?
C2 C7 H7 120.1 . . ?
N3 C8 C12 122.16(11) . . ?
N3 C8 C1 114.53(10) . . ?
C12 C8 C1 123.31(11) . . ?
N3 C9 C10 123.44(11) . . ?
N3 C9 H9 118.3 . . ?
C10 C9 H9 118.3 . . ?
C9 C10 C11 118.34(12) . . ?
C9 C10 H10 120.8 . . ?
C11 C10 H10 120.8 . . ?
C12 C11 C10 119.28(11) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C11 C12 C8 118.84(11) . . ?
C11 C12 H12 120.6 . . ?
C8 C12 H12 120.6 . . ?
N4 C13 C5 178.38(14) . . ?
C1 N1 N2 114.89(10) . . ?
N1 N2 C2 121.45(10) . . ?
N1 N2 H2N 116.5(12) . . ?
C2 N2 H2N 121.9(12) . . ?
C9 N3 C8 117.93(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C8 N3 -172.65(11) . . . . ?
N1 C1 C8 C12 7.63(18) . . . . ?
C8 C1 N1 N2 -178.84(10) . . . . ?
C1 N1 N2 C2 179.61(11) . . . . ?
C3 C2 N2 N1 -173.39(10) . . . . ?
C7 C2 N2 N1 7.01(18) . . . . ?

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
N2 H2N N3 0.885(9) 2.079(9) 2.9606(14) 174.0(17) 2_545

_refine_diff_density_max         0.324
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.127


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# 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_16022a4NNC
_database_code_depnum_ccdc_archive 'CCDC 1491534'
_audit_update_record             
;
2016-07-07 deposited with the CCDC.
2016-08-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '4-CNbenzaldehyde 2-(5Br-2pyridinyl)hydrazone'
_chemical_name_common            ?
_chemical_melting_point          '523-526 K'
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H9 Br N4'
_chemical_formula_weight         301.15

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                   12.552(5)
_cell_length_b                   3.962(3)
_cell_length_c                   25.17(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.71(3)
_cell_angle_gamma                90
_cell_volume                     1220.9(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    2879
_cell_measurement_theta_min      3.66
_cell_measurement_theta_max      74.39

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.053
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    4.478
_shelx_estimated_absorpt_T_min   0.401
_shelx_estimated_absorpt_T_max   0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4795
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_process_details   'SADABS-2014 (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'ImuS micro-focus'
_diffrn_measurement_device_type  'Bruker-AXS D8 Venture PHOTON-II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14181
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.600
_diffrn_reflns_theta_max         74.484
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2480
_reflns_number_gt                2163
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'PLATON (Spek 2009) Mercury (Macrae et al. 2008)'
_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)+4.7349P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2480
_refine_ls_number_parameters     166
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.0954
_refine_ls_wR_factor_gt          0.0882
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_restrained_S_all      1.127
_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
Br1 Br -0.13070(3) 0.65794(10) 0.28322(2) 0.02922(13) Uani 1 1 d . . . . .
C1 C 0.2811(2) 0.2801(9) 0.56903(13) 0.0229(7) Uani 1 1 d . . . . .
H1 H 0.2412 0.1454 0.5891 0.028 Uiso 1 1 calc R U . . .
C2 C 0.3896(3) 0.4043(9) 0.59583(13) 0.0223(7) Uani 1 1 d . . . . .
C3 C 0.4261(3) 0.3533(10) 0.65169(13) 0.0235(7) Uani 1 1 d . . . . .
H3 H 0.3804 0.2399 0.6714 0.028 Uiso 1 1 calc R U . . .
C4 C 0.5284(3) 0.4663(10) 0.67879(13) 0.0256(7) Uani 1 1 d . . . . .
H4 H 0.5525 0.4323 0.7169 0.031 Uiso 1 1 calc R U . . .
C5 C 0.5951(3) 0.6299(10) 0.64950(14) 0.0239(7) Uani 1 1 d . . . . .
C6 C 0.5596(3) 0.6831(10) 0.59344(14) 0.0257(7) Uani 1 1 d . . . . .
H6 H 0.6055 0.7956 0.5737 0.031 Uiso 1 1 calc R U . . .
C7 C 0.4572(3) 0.5708(10) 0.56690(13) 0.0250(7) Uani 1 1 d . . . . .
H7 H 0.4328 0.6070 0.5289 0.030 Uiso 1 1 calc R U . . .
C8 C 0.0824(2) 0.3296(9) 0.44789(13) 0.0210(7) Uani 1 1 d . . . . .
C9 C -0.0805(2) 0.3246(10) 0.38504(13) 0.0226(7) Uani 1 1 d . . . . .
H9 H -0.1548 0.2565 0.3745 0.027 Uiso 1 1 calc R U . . .
C10 C -0.0381(3) 0.5190(9) 0.34971(13) 0.0221(7) Uani 1 1 d . . . . .
C11 C 0.0701(3) 0.6247(9) 0.36384(14) 0.0236(7) Uani 1 1 d . . . . .
H11 H 0.1007 0.7592 0.3397 0.028 Uiso 1 1 calc R U . . .
C12 C 0.1313(3) 0.5288(10) 0.41370(13) 0.0230(7) Uani 1 1 d . . . . .
H12 H 0.2055 0.5960 0.4249 0.028 Uiso 1 1 calc R U . . .
C13 C 0.7007(3) 0.7566(10) 0.67753(14) 0.0258(8) Uani 1 1 d . . . . .
H2N H 0.101(3) 0.106(10) 0.5181(14) 0.031 Uiso 1 1 d D U . . .
N1 N 0.2390(2) 0.3490(8) 0.51926(11) 0.0219(6) Uani 1 1 d . . . . .
N2 N 0.1374(2) 0.2247(8) 0.49834(11) 0.0232(6) Uani 1 1 d D . . . .
N3 N -0.0223(2) 0.2255(8) 0.43391(11) 0.0220(6) Uani 1 1 d . . . . .
N4 N 0.7843(2) 0.8584(9) 0.69882(12) 0.0317(7) 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 C10 1.897(3) . ?
C1 N1 1.277(4) . ?
C1 C2 1.466(4) . ?
C1 H1 0.95 . ?
C2 C3 1.394(5) . ?
C2 C7 1.399(5) . ?
C3 C4 1.389(5) . ?
C3 H3 0.95 . ?
C4 C5 1.391(5) . ?
C4 H4 0.95 . ?
C5 C6 1.399(5) . ?
C5 C13 1.448(5) . ?
C6 C7 1.385(5) . ?
C6 H6 0.95 . ?
C7 H7 0.95 . ?
C8 N3 1.349(4) . ?
C8 N2 1.370(4) . ?
C8 C12 1.404(5) . ?
C9 N3 1.344(4) . ?
C9 C10 1.370(5) . ?
C9 H9 0.95 . ?
C10 C11 1.390(5) . ?
C11 C12 1.373(5) . ?
C11 H11 0.95 . ?
C12 H12 0.95 . ?
C13 N4 1.141(5) . ?
N1 N2 1.361(4) . ?
N2 H2N 0.879(10) . ?

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
N1 C1 C2 121.4(3) . . ?
N1 C1 H1 119.3 . . ?
C2 C1 H1 119.3 . . ?
C3 C2 C7 119.4(3) . . ?
C3 C2 C1 118.7(3) . . ?
C7 C2 C1 121.8(3) . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 119.3(3) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C6 120.6(3) . . ?
C4 C5 C13 119.8(3) . . ?
C6 C5 C13 119.5(3) . . ?
C7 C6 C5 119.6(3) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C6 C7 C2 120.4(3) . . ?
C6 C7 H7 119.8 . . ?
C2 C7 H7 119.8 . . ?
N3 C8 N2 114.3(3) . . ?
N3 C8 C12 123.0(3) . . ?
N2 C8 C12 122.7(3) . . ?
N3 C9 C10 123.2(3) . . ?
N3 C9 H9 118.4 . . ?
C10 C9 H9 118.4 . . ?
C9 C10 C11 120.1(3) . . ?
C9 C10 Br1 119.0(2) . . ?
C11 C10 Br1 120.8(3) . . ?
C12 C11 C10 118.0(3) . . ?
C12 C11 H11 121.0 . . ?
C10 C11 H11 121.0 . . ?
C11 C12 C8 118.9(3) . . ?
C11 C12 H12 120.5 . . ?
C8 C12 H12 120.5 . . ?
N4 C13 C5 178.9(4) . . ?
C1 N1 N2 116.9(3) . . ?
N1 N2 C8 119.2(3) . . ?
N1 N2 H2N 122(3) . . ?
C8 N2 H2N 118(3) . . ?
C9 N3 C8 116.9(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
N1 C1 C2 C3 172.9(3) . . . . ?
N1 C1 C2 C7 -7.3(6) . . . . ?
C2 C1 N1 N2 -179.3(3) . . . . ?
C1 N1 N2 C8 170.9(3) . . . . ?
N3 C8 N2 N1 -172.0(3) . . . . ?
C12 C8 N2 N1 8.0(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
N2 H2N N3 0.879(10) 2.166(12) 3.043(4) 175(4) 3_556

_refine_diff_density_max         0.861
_refine_diff_density_min         -0.684
_refine_diff_density_rms         0.109


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# 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_15154a4CNN
_database_code_depnum_ccdc_archive 'CCDC 1491535'
_audit_update_record             
;
2016-07-07 deposited with the CCDC.
2016-08-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
5-Br-2-pyrcarboxaldehyde-4-CNphenylhydrazoneH2O
_chemical_name_common            ?
_chemical_melting_point          '481-482 K'
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H11 Br N4 O'
_chemical_formula_weight         319.17

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   6.7356(10)
_cell_length_b                   10.0422(15)
_cell_length_c                   10.4886(16)
_cell_angle_alpha                94.501(2)
_cell_angle_beta                 105.094(2)
_cell_angle_gamma                98.124(2)
_cell_volume                     673.15(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2092
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      27.34

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_F_000             320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    3.051
_shelx_estimated_absorpt_T_min   0.516
_shelx_estimated_absorpt_T_max   0.792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5697
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS 2012/1 (Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6751
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.026
_diffrn_reflns_theta_max         27.383
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2989
_reflns_number_gt                2631
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'PLATON (Spek 2009) Mercury (Macrae et al. 2008)'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0278P)²+0.2108P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2989
_refine_ls_number_parameters     182
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0267
_refine_ls_wR_factor_ref         0.0621
_refine_ls_wR_factor_gt          0.0597
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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 0.22038(3) 0.66594(2) 0.66824(2) 0.03441(8) Uani 1 1 d . . . . .
C1 C 0.7707(3) 0.2407(2) 0.65238(19) 0.0270(4) Uani 1 1 d . . . . .
H1 H 0.7105 0.1594 0.5941 0.032 Uiso 1 1 calc R U . . .
C2 C 1.2644(3) 0.1580(2) 0.79436(18) 0.0254(4) Uani 1 1 d . . . . .
C3 C 1.3675(3) 0.0494(2) 0.7786(2) 0.0298(4) Uani 1 1 d . . . . .
H3 H 1.2999 -0.0254 0.7132 0.036 Uiso 1 1 calc R U . . .
C4 C 1.5664(3) 0.0496(2) 0.8571(2) 0.0289(4) Uani 1 1 d . . . . .
H4 H 1.6344 -0.0257 0.8470 0.035 Uiso 1 1 calc R U . . .
C5 C 1.6677(3) 0.1605(2) 0.95149(19) 0.0269(4) Uani 1 1 d . . . . .
C6 C 1.5651(3) 0.2698(2) 0.96549(19) 0.0291(4) Uani 1 1 d . . . . .
H6 H 1.6344 0.3460 1.0288 0.035 Uiso 1 1 calc R U . . .
C7 C 1.3647(3) 0.2688(2) 0.88864(19) 0.0277(4) Uani 1 1 d . . . . .
H7 H 1.2954 0.3431 0.8999 0.033 Uiso 1 1 calc R U . . .
C8 C 0.6488(3) 0.3482(2) 0.66032(18) 0.0245(4) Uani 1 1 d . . . . .
C9 C 0.3302(3) 0.4164(2) 0.58895(18) 0.0263(4) Uani 1 1 d . . . . .
H9 H 0.1897 0.3988 0.5354 0.032 Uiso 1 1 calc R U . . .
C10 C 0.4018(3) 0.5384(2) 0.66928(19) 0.0258(4) Uani 1 1 d . . . . .
C11 C 0.6067(3) 0.5668(2) 0.74828(19) 0.0285(4) Uani 1 1 d . . . . .
H11 H 0.6595 0.6505 0.8038 0.034 Uiso 1 1 calc R U . . .
C12 C 0.7305(3) 0.4701(2) 0.74343(19) 0.0284(4) Uani 1 1 d . . . . .
H12 H 0.8713 0.4860 0.7964 0.034 Uiso 1 1 calc R U . . .
C13 C 1.8737(3) 0.1615(2) 1.0362(2) 0.0310(5) Uani 1 1 d . . . . .
H1O H 0.258(3) 0.165(2) 0.4478(17) 0.047 Uiso 1 1 d D U . . .
N1 N 0.9607(3) 0.25635(17) 0.72489(16) 0.0274(4) Uani 1 1 d . . . . .
N2 N 1.0649(3) 0.15224(17) 0.71339(17) 0.0298(4) Uani 1 1 d D . . . .
H2N H 1.005(3) 0.0779(15) 0.6604(18) 0.036 Uiso 1 1 d D U . . .
N3 N 0.4501(2) 0.32203(16) 0.58332(15) 0.0256(3) Uani 1 1 d . . . . .
N4 N 2.0348(3) 0.1623(2) 1.10591(19) 0.0391(4) Uani 1 1 d . . . . .
O1 O 0.1617(3) 0.11464(19) 0.39344(18) 0.0545(5) Uani 1 1 d D . . . .
H2O H 0.162(4) 0.142(3) 0.3225(14) 0.058(9) Uiso 1 1 d 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 C10 1.8901(19) . ?
C1 N1 1.288(3) . ?
C1 C8 1.456(3) . ?
C1 H1 0.95 . ?
C2 N2 1.381(2) . ?
C2 C7 1.392(3) . ?
C2 C3 1.394(3) . ?
C3 C4 1.377(3) . ?
C3 H3 0.95 . ?
C4 C5 1.395(3) . ?
C4 H4 0.95 . ?
C5 C6 1.395(3) . ?
C5 C13 1.438(3) . ?
C6 C7 1.379(3) . ?
C6 H6 0.95 . ?
C7 H7 0.95 . ?
C8 N3 1.348(2) . ?
C8 C12 1.398(3) . ?
C9 N3 1.337(2) . ?
C9 C10 1.379(3) . ?
C9 H9 0.95 . ?
C10 C11 1.389(3) . ?
C11 C12 1.373(3) . ?
C11 H11 0.95 . ?
C12 H12 0.95 . ?
C13 N4 1.138(3) . ?
N1 N2 1.354(2) . ?
N2 H2N 0.873(10) . ?
O1 H1O 0.815(10) . ?
O1 H2O 0.812(10) . ?

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
N1 C1 C8 119.56(18) . . ?
N1 C1 H1 120.2 . . ?
C8 C1 H1 120.2 . . ?
N2 C2 C7 122.08(18) . . ?
N2 C2 C3 118.16(18) . . ?
C7 C2 C3 119.76(18) . . ?
C4 C3 C2 120.61(19) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.83(18) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 119.35(18) . . ?
C6 C5 C13 119.94(19) . . ?
C4 C5 C13 120.69(18) . . ?
C7 C6 C5 120.89(19) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C2 119.54(18) . . ?
C6 C7 H7 120.2 . . ?
C2 C7 H7 120.2 . . ?
N3 C8 C12 121.90(18) . . ?
N3 C8 C1 115.61(17) . . ?
C12 C8 C1 122.49(18) . . ?
N3 C9 C10 122.77(18) . . ?
N3 C9 H9 118.6 . . ?
C10 C9 H9 118.6 . . ?
C9 C10 C11 119.75(18) . . ?
C9 C10 Br1 119.41(14) . . ?
C11 C10 Br1 120.83(15) . . ?
C12 C11 C10 117.80(19) . . ?
C12 C11 H11 121.1 . . ?
C10 C11 H11 121.1 . . ?
C11 C12 C8 119.81(18) . . ?
C11 C12 H12 120.1 . . ?
C8 C12 H12 120.1 . . ?
N4 C13 C5 178.3(2) . . ?
C1 N1 N2 116.59(17) . . ?
N1 N2 C2 119.85(17) . . ?
N1 N2 H2N 121.5(15) . . ?
C2 N2 H2N 118.5(15) . . ?
C9 N3 C8 117.98(17) . . ?
H1O O1 H2O 104.8(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C8 N3 -178.55(17) . . . . ?
N1 C1 C8 C12 0.6(3) . . . . ?
C8 C1 N1 N2 179.59(16) . . . . ?
C1 N1 N2 C2 -175.72(18) . . . . ?
C3 C2 N2 N1 -179.38(17) . . . . ?
C7 C2 N2 N1 -0.2(3) . . . . ?

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
O1 H2O N4 0.812(10) 2.247(13) 3.009(3) 156(2) 1_354
N2 H2N O1 0.873(10) 2.050(13) 2.872(2) 157(2) 2_656
O1 H1O N3 0.815(10) 2.076(12) 2.875(2) 166(3) .

_refine_diff_density_max         0.395
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.057


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
