# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1971665'
loop_
_audit_author_name
_audit_author_address
'Zhenfeng Zhang'
;School of Chemistry and Chemical Engineering, Henan Normal University
China
;
_audit_update_record             
;
2019-12-12 deposited with the CCDC.	2020-02-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        
;
2-cyano-N'-[(1E)-(4-methylphenyl)methylidene]acetohydrazide
;
_chemical_name_common            
;
4-methylbenzaldehyde (cyanoacetyl)hydrazone
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H11 N3 O'
_chemical_formula_sum            'C11 H11 N3 O'
_chemical_formula_weight         201.23

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

_space_group_crystal_system      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                   4.5912(4)
_cell_length_b                   10.6146(7)
_cell_length_c                   21.6437(17)
_cell_angle_alpha                90
_cell_angle_beta                 94.490(8)
_cell_angle_gamma                90
_cell_volume                     1051.54(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2617
_cell_measurement_theta_min      4.2690
_cell_measurement_theta_max      28.2490

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.67737
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7121
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.422
_diffrn_reflns_theta_max         28.904
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.895
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.895
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.895
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2483
_reflns_number_gt                1993
_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       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0597P)²+0.3358P] 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     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.008(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2483
_refine_ls_number_parameters     170
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0540
_refine_ls_wR_factor_ref         0.1463
_refine_ls_wR_factor_gt          0.1377
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_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
O1 O -0.0548(3) 0.64456(11) 0.45266(6) 0.0469(3) Uani 1 1 d . . . . .
N2 N 0.5251(3) 0.65337(13) 0.56686(6) 0.0370(3) Uani 1 1 d . . . . .
N1 N 0.2953(3) 0.60709(13) 0.52884(6) 0.0375(3) Uani 1 1 d . . . . .
C1 C 0.1565(3) 0.68119(15) 0.48601(8) 0.0368(4) Uani 1 1 d . . . . .
C5 C 0.8683(3) 0.61592(15) 0.65328(7) 0.0350(4) Uani 1 1 d . . . . .
C4 C 0.6329(3) 0.57785(16) 0.60821(8) 0.0367(4) Uani 1 1 d . . . . .
C10 C 0.9792(4) 0.73869(16) 0.65589(8) 0.0393(4) Uani 1 1 d . . . . .
C8 C 1.3008(4) 0.68608(17) 0.74586(8) 0.0417(4) Uani 1 1 d . . . . .
C9 C 1.1933(4) 0.77159(17) 0.70107(8) 0.0426(4) Uani 1 1 d . . . . .
C6 C 0.9828(4) 0.52942(17) 0.69653(8) 0.0436(4) Uani 1 1 d . . . . .
C7 C 1.1943(4) 0.56464(18) 0.74230(9) 0.0468(4) Uani 1 1 d . . . . .
C2 C 0.2830(5) 0.81196(18) 0.48092(11) 0.0524(5) Uani 1 1 d . . . . .
N3 N -0.0575(5) 0.95964(19) 0.41351(11) 0.0855(7) Uani 1 1 d . . . . .
C3 C 0.0902(5) 0.89343(18) 0.44247(9) 0.0562(5) Uani 1 1 d . . . . .
C11 C 1.5257(4) 0.7241(2) 0.79659(9) 0.0581(5) Uani 1 1 d . . . . .
H11A H 1.431915 0.767469 0.828517 0.087 Uiso 1 1 calc R U . . .
H11B H 1.666638 0.778799 0.779961 0.087 Uiso 1 1 calc R U . . .
H11C H 1.622371 0.650320 0.813700 0.087 Uiso 1 1 calc R U . . .
H1 H 0.221(4) 0.528(2) 0.5354(8) 0.047(5) Uiso 1 1 d . . . . .
H4 H 0.555(4) 0.4947(19) 0.6112(8) 0.046(5) Uiso 1 1 d . . . . .
H6 H 0.911(4) 0.440(2) 0.6952(9) 0.055(5) Uiso 1 1 d . . . . .
H9 H 1.275(4) 0.8582(19) 0.7000(9) 0.047(5) Uiso 1 1 d . . . . .
H10 H 0.906(4) 0.7986(19) 0.6245(9) 0.049(5) Uiso 1 1 d . . . . .
H7 H 1.270(4) 0.506(2) 0.7719(9) 0.059(6) Uiso 1 1 d . . . . .
H2A H 0.315(5) 0.854(2) 0.5223(12) 0.081(8) Uiso 1 1 d . . . . .
H2B H 0.471(6) 0.807(2) 0.4637(12) 0.083(8) Uiso 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
O1 C1 1.2262(19) . ?
N2 C4 1.273(2) . ?
N2 N1 1.3767(18) . ?
N1 C1 1.338(2) . ?
N1 H1 0.93(2) . ?
C1 C2 1.512(2) . ?
C5 C6 1.385(2) . ?
C5 C10 1.399(2) . ?
C5 C4 1.455(2) . ?
C4 H4 0.96(2) . ?
C10 C9 1.376(2) . ?
C10 H10 0.97(2) . ?
C8 C7 1.379(3) . ?
C8 C9 1.390(3) . ?
C8 C11 1.503(2) . ?
C9 H9 0.99(2) . ?
C6 C7 1.383(3) . ?
C6 H6 1.00(2) . ?
C7 H7 0.94(2) . ?
C2 C3 1.452(3) . ?
C2 H2A 1.00(3) . ?
C2 H2B 0.97(3) . ?
N3 C3 1.132(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N2 N1 115.69(14) . . ?
C1 N1 N2 120.36(14) . . ?
C1 N1 H1 118.8(11) . . ?
N2 N1 H1 120.5(11) . . ?
O1 C1 N1 122.23(15) . . ?
O1 C1 C2 122.60(15) . . ?
N1 C1 C2 115.16(15) . . ?
C6 C5 C10 118.20(15) . . ?
C6 C5 C4 119.45(15) . . ?
C10 C5 C4 122.33(15) . . ?
N2 C4 C5 121.62(15) . . ?
N2 C4 H4 120.1(11) . . ?
C5 C4 H4 118.3(11) . . ?
C9 C10 C5 120.18(16) . . ?
C9 C10 H10 121.3(12) . . ?
C5 C10 H10 118.5(12) . . ?
C7 C8 C9 117.82(16) . . ?
C7 C8 C11 120.82(17) . . ?
C9 C8 C11 121.36(17) . . ?
C10 C9 C8 121.65(16) . . ?
C10 C9 H9 117.9(11) . . ?
C8 C9 H9 120.4(11) . . ?
C7 C6 C5 120.85(17) . . ?
C7 C6 H6 119.2(11) . . ?
C5 C6 H6 120.0(11) . . ?
C8 C7 C6 121.25(17) . . ?
C8 C7 H7 118.2(13) . . ?
C6 C7 H7 120.6(13) . . ?
C3 C2 C1 111.60(16) . . ?
C3 C2 H2A 106.5(14) . . ?
C1 C2 H2A 112.1(15) . . ?
C3 C2 H2B 109.6(15) . . ?
C1 C2 H2B 109.6(16) . . ?
H2A C2 H2B 107(2) . . ?
N3 C3 C2 178.1(2) . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N2 N1 C1 176.43(14) . . . . ?
N2 N1 C1 O1 -177.63(14) . . . . ?
N2 N1 C1 C2 3.6(2) . . . . ?
N1 N2 C4 C5 -177.34(13) . . . . ?
C6 C5 C4 N2 -178.56(15) . . . . ?
C10 C5 C4 N2 3.3(2) . . . . ?
C6 C5 C10 C9 -0.9(2) . . . . ?
C4 C5 C10 C9 177.19(15) . . . . ?
C5 C10 C9 C8 -1.4(3) . . . . ?
C7 C8 C9 C10 2.5(3) . . . . ?
C11 C8 C9 C10 -177.48(16) . . . . ?
C10 C5 C6 C7 2.1(3) . . . . ?
C4 C5 C6 C7 -176.08(16) . . . . ?
C9 C8 C7 C6 -1.4(3) . . . . ?
C11 C8 C7 C6 178.66(17) . . . . ?
C5 C6 C7 C8 -1.0(3) . . . . ?
O1 C1 C2 C3 12.2(3) . . . . ?
N1 C1 C2 C3 -169.04(17) . . . . ?

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
_geom_hbond_publ_flag
N1 H1 O1 0.93(2) 2.00(2) 2.9300(19) 178.4(17) 3_566 yes

_refine_diff_density_max         0.253
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_zzf-2
_database_code_depnum_ccdc_archive 'CCDC 1971666'
loop_
_audit_author_name
_audit_author_address
'Zhenfeng Zhang'
;School of Chemistry and Chemical Engineering, Henan Normal University
China
;
_audit_update_record             
;
2019-12-12 deposited with the CCDC.	2020-02-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        
;
2-cyano-N'-[(1E)-(4-chlorophenyl)methylidene]acetohydrazide
;
_chemical_name_common            
;
4-chlorobenzaldehyde (cyanoacetyl)hydrazone
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H8 Cl N3 O'
_chemical_formula_sum            'C10 H8 Cl N3 O'
_chemical_formula_weight         221.64

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'
O O 0.0492 0.0322 '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       
;
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                   4.59060(10)
_cell_length_b                   10.7866(2)
_cell_length_c                   20.7507(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.248(2)
_cell_angle_gamma                90
_cell_volume                     1024.69(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3465
_cell_measurement_theta_min      4.3
_cell_measurement_theta_max      71.0

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    3.110
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.87737
_exptl_absorpt_correction_T_max  0.98000
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4974
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.273
_diffrn_reflns_theta_max         71.130
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1968
_reflns_number_gt                1827
_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       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0690P)²+0.3047P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0218(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1968
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.1109
_refine_ls_wR_factor_gt          0.1087
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.55000(9) 0.27685(5) 0.19669(2) 0.0515(2) Uani 1 1 d . . . . .
O1 O 1.0684(3) 0.13595(11) 0.55350(6) 0.0425(3) Uani 1 1 d . . . . .
N1 N 0.7096(3) 0.11059(13) 0.47480(7) 0.0357(3) Uani 1 1 d . . . . .
N2 N 0.4834(3) 0.16238(13) 0.43656(6) 0.0344(3) Uani 1 1 d . . . . .
C1 C 0.8587(3) 0.17818(15) 0.52050(7) 0.0342(4) Uani 1 1 d . . . . .
C9 C -0.1805(4) 0.30314(16) 0.30354(8) 0.0383(4) Uani 1 1 d . . . . .
C5 C 0.1322(3) 0.13858(14) 0.34707(7) 0.0323(4) Uani 1 1 d . . . . .
C6 C 0.0068(4) 0.05901(17) 0.30011(9) 0.0400(4) Uani 1 1 d . . . . .
C4 C 0.3664(3) 0.09270(15) 0.39242(8) 0.0347(4) Uani 1 1 d . . . . .
C10 C 0.0342(4) 0.26147(16) 0.34826(8) 0.0360(4) Uani 1 1 d . . . . .
C8 C -0.2929(4) 0.22294(16) 0.25576(8) 0.0368(4) Uani 1 1 d . . . . .
C7 C -0.2044(4) 0.10058(17) 0.25409(9) 0.0414(4) Uani 1 1 d . . . . .
C3 C 0.9636(5) 0.38781(17) 0.56338(10) 0.0501(5) Uani 1 1 d . . . . .
C2 C 0.7471(4) 0.30893(17) 0.52915(11) 0.0475(5) Uani 1 1 d . . . . .
N3 N 1.1301(5) 0.45299(18) 0.58817(12) 0.0774(7) Uani 1 1 d . . . . .
H1 H 0.764(5) 0.038(3) 0.4667(11) 0.056(6) Uiso 1 1 d . . . . .
H4 H 0.425(4) 0.006(2) 0.3879(9) 0.040(5) Uiso 1 1 d . . . . .
H6 H 0.069(4) -0.025(2) 0.3000(10) 0.052(6) Uiso 1 1 d . . . . .
H9 H -0.244(4) 0.389(2) 0.3043(9) 0.042(5) Uiso 1 1 d . . . . .
H10 H 0.104(5) 0.320(2) 0.3813(11) 0.054(6) Uiso 1 1 d . . . . .
H7 H -0.285(5) 0.043(2) 0.2213(12) 0.060(6) Uiso 1 1 d . . . . .
H2A H 0.573(6) 0.306(3) 0.5534(12) 0.073(8) Uiso 1 1 d . . . . .
H2B H 0.690(5) 0.352(2) 0.4883(13) 0.065(7) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C8 1.7376(17) . ?
O1 C1 1.2268(19) . ?
N1 C1 1.343(2) . ?
N1 N2 1.3778(18) . ?
N1 H1 0.85(3) . ?
N2 C4 1.272(2) . ?
C1 C2 1.516(2) . ?
C9 C10 1.378(2) . ?
C9 C8 1.386(2) . ?
C9 H9 0.97(2) . ?
C5 C6 1.391(2) . ?
C5 C10 1.401(2) . ?
C5 C4 1.462(2) . ?
C6 C7 1.384(2) . ?
C6 H6 0.95(2) . ?
C4 H4 0.98(2) . ?
C10 H10 0.97(2) . ?
C8 C7 1.382(2) . ?
C7 H7 0.98(2) . ?
C3 N3 1.133(3) . ?
C3 C2 1.453(3) . ?
C2 H2A 0.98(3) . ?
C2 H2B 0.98(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 N2 120.65(14) . . ?
C1 N1 H1 120.1(15) . . ?
N2 N1 H1 118.9(15) . . ?
C4 N2 N1 115.78(14) . . ?
O1 C1 N1 122.04(15) . . ?
O1 C1 C2 122.52(15) . . ?
N1 C1 C2 115.44(14) . . ?
C10 C9 C8 119.20(15) . . ?
C10 C9 H9 120.0(11) . . ?
C8 C9 H9 120.7(11) . . ?
C6 C5 C10 118.66(15) . . ?
C6 C5 C4 119.25(15) . . ?
C10 C5 C4 122.07(14) . . ?
C7 C6 C5 121.05(16) . . ?
C7 C6 H6 120.1(12) . . ?
C5 C6 H6 118.8(12) . . ?
N2 C4 C5 120.96(14) . . ?
N2 C4 H4 121.9(11) . . ?
C5 C4 H4 117.1(11) . . ?
C9 C10 C5 120.75(15) . . ?
C9 C10 H10 116.7(14) . . ?
C5 C10 H10 122.4(14) . . ?
C7 C8 C9 121.29(16) . . ?
C7 C8 Cl1 119.18(13) . . ?
C9 C8 Cl1 119.54(13) . . ?
C8 C7 C6 118.96(16) . . ?
C8 C7 H7 122.2(14) . . ?
C6 C7 H7 118.8(14) . . ?
N3 C3 C2 177.1(2) . . ?
C3 C2 C1 112.19(15) . . ?
C3 C2 H2A 108.9(16) . . ?
C1 C2 H2A 109.3(17) . . ?
C3 C2 H2B 106.0(15) . . ?
C1 C2 H2B 113.9(15) . . ?
H2A C2 H2B 106(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
_geom_hbond_publ_flag
N1 H1 O1 0.85(3) 2.08(3) 2.9231(19) 175(2) 3_756 yes

_refine_diff_density_max         0.215
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_zzf-20190530
_database_code_depnum_ccdc_archive 'CCDC 1971667'
loop_
_audit_author_name
_audit_author_address
'Zhenfeng Zhang'
;School of Chemistry and Chemical Engineering, Henan Normal University
China
;
_audit_update_record             
;
2019-12-12 deposited with the CCDC.	2020-02-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        
;
2-cyano-N'-[(1E)-(4-bromophenyl)methylidene]acetohydrazide
;
_chemical_name_common            
;
4-bromobenzaldehyde (cyanoacetyl)hydrazone
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H8 Br N3 O'
_chemical_formula_sum            'C10 H8 Br N3 O'
_chemical_formula_weight         266.10

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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                   4.63410(10)
_cell_length_b                   10.7786(3)
_cell_length_c                   21.0532(8)
_cell_angle_alpha                90
_cell_angle_beta                 93.975(3)
_cell_angle_gamma                90
_cell_volume                     1049.06(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3343
_cell_measurement_theta_min      3.5
_cell_measurement_theta_max      29.6

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.685
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    3.894
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.87737
_exptl_absorpt_correction_T_max  0.98000
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8239
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.470
_diffrn_reflns_theta_max         29.594
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.852
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.852
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2518
_reflns_number_gt                1934
_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       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0273P)²+0.4024P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0027(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2518
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0765
_refine_ls_wR_factor_gt          0.0671
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.002
_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 1.55628(5) 0.26639(3) 0.80706(2) 0.04639(13) Uani 1 1 d . . . . .
O1 O -0.0624(3) 0.13913(17) 0.44829(9) 0.0412(5) Uani 1 1 d . . . . .
N2 N 0.5149(4) 0.16094(18) 0.56373(10) 0.0321(5) Uani 1 1 d . . . . .
N1 N 0.2908(4) 0.1102(2) 0.52535(11) 0.0333(5) Uani 1 1 d . . . . .
C5 C 0.8612(5) 0.1334(2) 0.65148(12) 0.0303(5) Uani 1 1 d . . . . .
C8 C 1.2815(5) 0.2121(2) 0.74197(13) 0.0327(6) Uani 1 1 d . . . . .
C4 C 0.6294(5) 0.0896(2) 0.60631(13) 0.0326(6) Uani 1 1 d . . . . .
C6 C 0.9829(5) 0.0519(3) 0.69652(14) 0.0378(6) Uani 1 1 d . . . . .
C10 C 0.9614(6) 0.2557(2) 0.65148(14) 0.0348(6) Uani 1 1 d . . . . .
C1 C 0.1435(5) 0.1803(2) 0.48123(13) 0.0328(6) Uani 1 1 d . . . . .
C9 C 1.1726(5) 0.2948(3) 0.69634(14) 0.0352(6) Uani 1 1 d . . . . .
C7 C 1.1909(5) 0.0909(3) 0.74253(15) 0.0395(7) Uani 1 1 d . . . . .
C2 C 0.2589(6) 0.3100(3) 0.47413(17) 0.0450(7) Uani 1 1 d . . . . .
N3 N -0.1059(7) 0.4568(3) 0.41331(17) 0.0805(10) Uani 1 1 d . . . . .
C3 C 0.0530(7) 0.3904(3) 0.43892(16) 0.0531(8) Uani 1 1 d . . . . .
H6 H 0.918(5) -0.027(3) 0.6955(12) 0.033(7) Uiso 1 1 d . . . . .
H10 H 0.879(5) 0.312(3) 0.6199(14) 0.041(7) Uiso 1 1 d . . . . .
H9 H 1.228(5) 0.375(3) 0.6942(13) 0.040(7) Uiso 1 1 d . . . . .
H7 H 1.263(6) 0.037(3) 0.7722(14) 0.048(8) Uiso 1 1 d . . . . .
H4 H 0.569(5) 0.006(2) 0.6128(12) 0.033(7) Uiso 1 1 d . . . . .
H1 H 0.225(6) 0.033(3) 0.5333(15) 0.065(10) Uiso 1 1 d . . . . .
H2A H 0.294(6) 0.351(3) 0.5151(16) 0.058(9) Uiso 1 1 d . . . . .
H2B H 0.436(6) 0.307(3) 0.4528(15) 0.061(9) Uiso 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 C8 1.897(2) . ?
O1 C1 1.223(3) . ?
N2 C4 1.269(3) . ?
N2 N1 1.383(3) . ?
N1 C1 1.346(3) . ?
N1 H1 0.91(3) . ?
C5 C6 1.384(4) . ?
C5 C10 1.397(3) . ?
C5 C4 1.463(3) . ?
C8 C7 1.372(4) . ?
C8 C9 1.381(4) . ?
C4 H4 0.95(3) . ?
C6 C7 1.384(4) . ?
C6 H6 0.91(3) . ?
C10 C9 1.379(4) . ?
C10 H10 0.96(3) . ?
C1 C2 1.509(4) . ?
C9 H9 0.90(3) . ?
C7 H7 0.90(3) . ?
C2 C3 1.454(4) . ?
C2 H2A 0.97(3) . ?
C2 H2B 0.96(3) . ?
N3 C3 1.136(4) . ?

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
C4 N2 N1 115.7(2) . . ?
C1 N1 N2 120.4(2) . . ?
C1 N1 H1 119(2) . . ?
N2 N1 H1 120(2) . . ?
C6 C5 C10 118.6(2) . . ?
C6 C5 C4 119.1(2) . . ?
C10 C5 C4 122.2(2) . . ?
C7 C8 C9 121.6(2) . . ?
C7 C8 Br1 118.6(2) . . ?
C9 C8 Br1 119.85(19) . . ?
N2 C4 C5 121.1(2) . . ?
N2 C4 H4 124.0(15) . . ?
C5 C4 H4 114.9(15) . . ?
C7 C6 C5 121.2(2) . . ?
C7 C6 H6 121.1(16) . . ?
C5 C6 H6 117.7(16) . . ?
C9 C10 C5 120.6(2) . . ?
C9 C10 H10 120.5(16) . . ?
C5 C10 H10 118.9(16) . . ?
O1 C1 N1 121.8(2) . . ?
O1 C1 C2 123.2(2) . . ?
N1 C1 C2 115.0(2) . . ?
C10 C9 C8 119.1(2) . . ?
C10 C9 H9 116.7(17) . . ?
C8 C9 H9 124.2(17) . . ?
C8 C7 C6 118.8(3) . . ?
C8 C7 H7 121.5(19) . . ?
C6 C7 H7 119.6(19) . . ?
C3 C2 C1 112.2(2) . . ?
C3 C2 H2A 104.0(18) . . ?
C1 C2 H2A 111.9(18) . . ?
C3 C2 H2B 109.5(19) . . ?
C1 C2 H2B 109(2) . . ?
H2A C2 H2B 110(3) . . ?
N3 C3 C2 177.2(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N2 N1 C1 176.1(2) . . . . ?
N1 N2 C4 C5 -177.7(2) . . . . ?
C6 C5 C4 N2 -179.0(2) . . . . ?
C10 C5 C4 N2 2.1(4) . . . . ?
C10 C5 C6 C7 2.7(4) . . . . ?
C4 C5 C6 C7 -176.2(2) . . . . ?
C6 C5 C10 C9 -1.4(4) . . . . ?
C4 C5 C10 C9 177.5(2) . . . . ?
N2 N1 C1 O1 -177.2(2) . . . . ?
N2 N1 C1 C2 5.0(3) . . . . ?
C5 C10 C9 C8 -0.9(4) . . . . ?
C7 C8 C9 C10 2.0(4) . . . . ?
Br1 C8 C9 C10 -176.4(2) . . . . ?
C9 C8 C7 C6 -0.7(4) . . . . ?
Br1 C8 C7 C6 177.7(2) . . . . ?
C5 C6 C7 C8 -1.7(4) . . . . ?
O1 C1 C2 C3 17.3(4) . . . . ?
N1 C1 C2 C3 -165.0(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
_geom_hbond_publ_flag
N1 H1 O1 0.91(3) 2.05(3) 2.955(3) 178(3) 3_556 yes

_refine_diff_density_max         0.475
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.067

