# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1533855'
_audit_update_record             
;
2017-02-20 deposited with the CCDC.
2017-08-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(1E,2E)-1-(4-ethoxybenzylidene)-2-(1-(4-nitrophenyl)ethylidene)hydrazine
_chemical_name_common            azine
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H17 N3 O3'
_chemical_formula_weight         311.33

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_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                   9.347
_cell_length_b                   9.949
_cell_length_c                   10.194
_cell_angle_alpha                106.19
_cell_angle_beta                 101.69
_cell_angle_gamma                110.10
_cell_volume                     806.8
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2876
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      25.35

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13588
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.447
_diffrn_reflns_theta_max         25.360
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             2872
_reflns_number_gt                2191
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1268P)²+0.0705P] 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         2872
_refine_ls_number_parameters     232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0624
_refine_ls_wR_factor_ref         0.1908
_refine_ls_wR_factor_gt          0.1706
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.48039(16) 0.82979(16) 0.05041(15) 0.0806(4) Uani 1 1 d . . . . .
C5 C 0.7574(2) 0.5959(2) -0.9012(2) 0.0710(5) Uani 1 1 d . . . . .
H5 H 0.6626 0.5558 -0.8809 0.085 Uiso 1 1 calc R U . . .
C10 C 0.6013(2) 0.7470(2) -0.3250(2) 0.0684(5) Uani 1 1 d . . . . .
C1 C 0.8958(2) 0.6134(2) -1.0703(2) 0.0694(5) Uani 1 1 d . . . . .
N1 N 0.8931(2) 0.5658(2) -1.2207(2) 0.0849(5) Uani 1 1 d . . . . .
C4 C 0.9004(2) 0.6999(2) -0.7869(2) 0.0664(5) Uani 1 1 d . . . . .
C6 C 0.7541(2) 0.5518(2) -1.0422(2) 0.0719(5) Uani 1 1 d . . . . .
H6 H 0.6585 0.4820 -1.1171 0.086 Uiso 1 1 calc R U . . .
N2 N 0.7652(2) 0.72216(19) -0.61772(17) 0.0763(5) Uani 1 1 d . . . . .
N3 N 0.7709(2) 0.7711(2) -0.47275(18) 0.0801(5) Uani 1 1 d . . . . .
C3 C 1.0401(2) 0.7580(2) -0.8214(2) 0.0792(6) Uani 1 1 d . . . . .
H3 H 1.1368 0.8266 -0.7472 0.095 Uiso 1 1 calc R U . . .
C7 C 0.9026(2) 0.7458(2) -0.6354(2) 0.0711(5) Uani 1 1 d . . . . .
O2 O 0.7722(2) 0.4584(2) -1.31383(18) 0.1104(6) Uani 1 1 d . . . . .
C12 C 0.6891(2) 0.8716(2) -0.0646(2) 0.0737(5) Uani 1 1 d . . . . .
H12 H 0.7720 0.9346 0.0231 0.088 Uiso 1 1 calc R U . . .
C11 C 0.7235(2) 0.8407(2) -0.1914(2) 0.0722(5) Uani 1 1 d . . . . .
H11 H 0.8301 0.8829 -0.1884 0.087 Uiso 1 1 calc R U . . .
O1 O 1.0112(2) 0.6349(3) -1.2476(2) 0.1272(7) Uani 1 1 d . . . . .
C14 C 0.4068(2) 0.7157(2) -0.1995(2) 0.0734(5) Uani 1 1 d . . . . .
C13 C 0.5292(2) 0.8080(2) -0.0676(2) 0.0680(5) Uani 1 1 d . . . . .
C2 C 1.0385(2) 0.7163(2) -0.9623(2) 0.0795(6) Uani 1 1 d . . . . .
H2 H 1.1323 0.7570 -0.9838 0.095 Uiso 1 1 calc R U . . .
C15 C 0.4423(2) 0.6853(2) -0.3251(2) 0.0749(5) Uani 1 1 d . . . . .
C9 C 0.6311(3) 0.7139(2) -0.4623(2) 0.0727(5) Uani 1 1 d . . . . .
C16 C 0.5992(3) 0.9181(3) 0.1917(2) 0.0778(5) Uani 1 1 d . . . . .
C17 C 0.5102(3) 0.9192(3) 0.2977(3) 0.0856(6) Uani 1 1 d . . . . .
C8 C 1.0595(3) 0.8157(3) -0.5147(3) 0.1087(8) Uani 1 1 d . . . . .
H8A H 1.1454 0.8218 -0.5542 0.163 Uiso 1 1 calc R U . . .
H8B H 1.0788 0.9177 -0.4543 0.163 Uiso 1 1 calc R U . . .
H8C H 1.0549 0.7526 -0.4582 0.163 Uiso 1 1 calc R U . . .
H14 H 0.299(4) 0.673(3) -0.201(3) 0.130 Uiso 1 1 d . U . . .
H15 H 0.352(4) 0.624(3) -0.424(3) 0.130 Uiso 1 1 d . U . . .
H9 H 0.536(4) 0.646(3) -0.552(3) 0.130 Uiso 1 1 d . U . . .
H16A H 0.663(4) 1.025(3) 0.204(3) 0.130 Uiso 1 1 d . U . . .
H16B H 0.668(4) 0.866(3) 0.208(3) 0.130 Uiso 1 1 d . U . . .
H17A H 0.442(4) 0.970(4) 0.285(4) 0.163 Uiso 1 1 d . U . . .
H17B H 0.592(5) 0.978(4) 0.400(4) 0.163 Uiso 1 1 d . U . . .
H17C H 0.443(4) 0.815(4) 0.293(4) 0.163 Uiso 1 1 d . U . . .


_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
O3 C13 1.359(2) . ?
O3 C16 1.434(2) . ?
C5 C6 1.371(3) . ?
C5 C4 1.400(3) . ?
C10 C15 1.399(3) . ?
C10 C11 1.400(3) . ?
C10 C9 1.452(3) . ?
C1 C2 1.370(3) . ?
C1 C6 1.381(3) . ?
C1 N1 1.465(3) . ?
N1 O1 1.214(2) . ?
N1 O2 1.221(3) . ?
C4 C3 1.394(3) . ?
C4 C7 1.477(3) . ?
N2 C7 1.284(2) . ?
N2 N3 1.405(2) . ?
N3 C9 1.273(2) . ?
C3 C2 1.375(3) . ?
C7 C8 1.496(3) . ?
C12 C11 1.372(3) . ?
C12 C13 1.398(3) . ?
C14 C15 1.367(3) . ?
C14 C13 1.388(3) . ?
C16 C17 1.492(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
C13 O3 C16 119.24(16) . . ?
C6 C5 C4 121.53(17) . . ?
C15 C10 C11 117.68(18) . . ?
C15 C10 C9 118.86(18) . . ?
C11 C10 C9 123.44(18) . . ?
C2 C1 C6 122.13(19) . . ?
C2 C1 N1 119.20(18) . . ?
C6 C1 N1 118.67(18) . . ?
O1 N1 O2 122.7(2) . . ?
O1 N1 C1 118.6(2) . . ?
O2 N1 C1 118.73(18) . . ?
C3 C4 C5 117.65(18) . . ?
C3 C4 C7 121.35(18) . . ?
C5 C4 C7 121.00(17) . . ?
C5 C6 C1 118.47(18) . . ?
C7 N2 N3 114.86(16) . . ?
C9 N3 N2 111.29(17) . . ?
C2 C3 C4 121.56(19) . . ?
N2 C7 C4 115.86(17) . . ?
N2 C7 C8 124.48(19) . . ?
C4 C7 C8 119.66(18) . . ?
C11 C12 C13 119.78(19) . . ?
C12 C11 C10 121.40(18) . . ?
C15 C14 C13 120.32(18) . . ?
O3 C13 C14 115.39(17) . . ?
O3 C13 C12 125.19(18) . . ?
C14 C13 C12 119.43(18) . . ?
C1 C2 C3 118.66(18) . . ?
C14 C15 C10 121.39(19) . . ?
N3 C9 C10 123.0(2) . . ?
O3 C16 C17 106.84(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
C2 C1 N1 O1 -10.3(3) . . . . ?
C6 C1 N1 O1 170.2(2) . . . . ?
C2 C1 N1 O2 169.59(19) . . . . ?
C6 C1 N1 O2 -9.9(3) . . . . ?
C6 C5 C4 C3 0.2(3) . . . . ?
C6 C5 C4 C7 -179.62(16) . . . . ?
C4 C5 C6 C1 -0.5(3) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
N1 C1 C6 C5 179.58(15) . . . . ?
C7 N2 N3 C9 -165.17(17) . . . . ?
C5 C4 C3 C2 0.6(3) . . . . ?
C7 C4 C3 C2 -179.66(17) . . . . ?
N3 N2 C7 C4 -178.07(14) . . . . ?
N3 N2 C7 C8 1.5(3) . . . . ?
C3 C4 C7 N2 161.16(18) . . . . ?
C5 C4 C7 N2 -19.1(3) . . . . ?
C3 C4 C7 C8 -18.5(3) . . . . ?
C5 C4 C7 C8 161.3(2) . . . . ?
C13 C12 C11 C10 0.4(3) . . . . ?
C15 C10 C11 C12 -0.1(3) . . . . ?
C9 C10 C11 C12 178.54(16) . . . . ?
C16 O3 C13 C14 177.35(17) . . . . ?
C16 O3 C13 C12 -3.3(3) . . . . ?
C15 C14 C13 O3 -179.60(16) . . . . ?
C15 C14 C13 C12 1.0(3) . . . . ?
C11 C12 C13 O3 179.85(15) . . . . ?
C11 C12 C13 C14 -0.8(3) . . . . ?
C6 C1 C2 C3 0.6(3) . . . . ?
N1 C1 C2 C3 -178.89(17) . . . . ?
C4 C3 C2 C1 -0.9(3) . . . . ?
C13 C14 C15 C10 -0.8(3) . . . . ?
C11 C10 C15 C14 0.3(3) . . . . ?
C9 C10 C15 C14 -178.41(17) . . . . ?
N2 N3 C9 C10 -179.06(15) . . . . ?
C15 C10 C9 N3 176.59(17) . . . . ?
C11 C10 C9 N3 -2.1(3) . . . . ?
C13 O3 C16 C17 -178.94(16) . . . . ?

_refine_diff_density_max         0.209
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.032

