# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_hz1
_audit_block_doi                 10.5517/cc1k5yym
_database_code_depnum_ccdc_archive 'CCDC 1435701'

_audit_update_record             
;
2015-11-09 deposited with the CCDC.
2016-01-25 downloaded from the CCDC.
;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
α-(3-methyl-4-(hydroxyimino)-2,5-cyclohexadien-1-ylidene)benzeneacetonitrile
_chemical_name_common            ?
_chemical_melting_point          '160.4~161.9 \%C'
_chemical_formula_moiety         'C15 H12 N2 O'
_chemical_formula_sum            'C15 H12 N2 O'
_chemical_formula_weight         236.27

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                   6.958(5)
_cell_length_b                   3.937(3)
_cell_length_c                   45.96(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.278(9)
_cell_angle_gamma                90
_cell_volume                     1258.6(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1534
_cell_measurement_theta_min      2.6597
_cell_measurement_theta_max      21.1933

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   0.602
_exptl_transmission_factor_max   0.882
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   sadabs

_exptl_special_details           ?

_diffrn_ambient_temperature      296(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            9322
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -59
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_theta_min         1.773
_diffrn_reflns_theta_max         27.410
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2791
_reflns_number_gt                1569
_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-2013 (Sheldrick, 2013)'
_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)+(0.1368P)²+0.3253P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.028(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2791
_refine_ls_number_parameters     250
_refine_ls_number_restraints     204
_refine_ls_R_factor_all          0.1307
_refine_ls_R_factor_gt           0.0784
_refine_ls_wR_factor_ref         0.2605
_refine_ls_wR_factor_gt          0.2199
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.001
_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
C1 C 0.3379(4) 0.7123(7) 0.16794(6) 0.0528(8) Uani 1 1 d . . . . .
C2 C 0.4591(5) 0.5748(8) 0.18957(7) 0.0657(9) Uani 1 1 d . . . . .
H2 H 0.5868 0.5308 0.1853 0.079 Uiso 1 1 calc R U . . .
C3 C 0.3951(7) 0.5036(9) 0.21665(8) 0.0857(12) Uani 1 1 d . . . . .
H3 H 0.4785 0.4113 0.2306 0.103 Uiso 1 1 calc R U . . .
C4 C 0.2049(9) 0.5691(12) 0.22338(8) 0.0992(15) Uani 1 1 d . . . . .
H4 H 0.1601 0.5175 0.2418 0.119 Uiso 1 1 calc R U . . .
C5 C 0.0834(6) 0.7102(12) 0.20276(8) 0.0920(13) Uani 1 1 d . . . . .
H5 H -0.0434 0.7569 0.2074 0.110 Uiso 1 1 calc R U . . .
C6 C 0.1481(5) 0.7837(9) 0.17509(7) 0.0659(9) Uani 1 1 d . . . . .
H6 H 0.0650 0.8806 0.1613 0.079 Uiso 1 1 calc R U . . .
C7 C 0.4125(4) 0.7888(7) 0.13890(6) 0.0516(7) Uani 1 1 d . . . . .
C8 C 0.309(3) 0.716(6) 0.1146(4) 0.040(2) Uani 0.466(5) 1 d . U P A 1
C9 C 0.126(2) 0.543(5) 0.1116(3) 0.0400(19) Uani 0.466(5) 1 d . U P A 1
H9 H 0.0642 0.4683 0.1282 0.048 Uiso 0.466(5) 1 calc R U P A 1
C10 C 0.043(2) 0.487(5) 0.0856(3) 0.040(2) Uani 0.466(5) 1 d . U P A 1
H10 H -0.0754 0.3789 0.0846 0.048 Uiso 0.466(5) 1 calc R U P A 1
C11 C 0.130(2) 0.586(4) 0.0591(3) 0.045(2) Uani 0.466(5) 1 d . U P A 1
C12 C 0.316(2) 0.757(5) 0.0608(4) 0.048(2) Uani 0.466(5) 1 d . U P A 1
C13 C 0.398(2) 0.817(5) 0.0884(3) 0.047(2) Uani 0.466(5) 1 d . U P A 1
H13 H 0.5156 0.9271 0.0897 0.056 Uiso 0.466(5) 1 calc R U P A 1
N2 N 0.070(3) 0.557(5) 0.0299(3) 0.106(7) Uani 0.466(5) 1 d . . P A 1
O1 O 0.2026(12) 0.683(3) 0.00346(16) 0.139(3) Uani 0.466(5) 1 d . . P A 1
H1 H 0.3142 0.7029 0.0093 0.209 Uiso 0.466(5) 1 calc R U P A 1
C15 C 0.4309(7) 0.8700(15) 0.03183(10) 0.0403(15) Uani 0.466(5) 1 d . . P A 1
H15A H 0.3556 1.0329 0.0210 0.060 Uiso 0.466(5) 1 calc R U P A 1
H15B H 0.4529 0.6740 0.0199 0.060 Uiso 0.466(5) 1 calc R U P A 1
H15C H 0.5519 0.9696 0.0375 0.060 Uiso 0.466(5) 1 calc R U P A 1
C8' C 0.341(2) 0.740(5) 0.1096(3) 0.041(2) Uani 0.534(5) 1 d . U P A 2
C9' C 0.157(2) 0.578(4) 0.1057(3) 0.047(2) Uani 0.534(5) 1 d . U P A 2
H9' H 0.0920 0.5055 0.1221 0.056 Uiso 0.534(5) 1 calc R U P A 2
C10' C 0.074(2) 0.527(4) 0.0789(3) 0.045(2) Uani 0.534(5) 1 d . U P A 2
C11' C 0.1719(18) 0.631(4) 0.0537(3) 0.044(2) Uani 0.534(5) 1 d . U P A 2
C12' C 0.3609(17) 0.790(4) 0.0569(3) 0.049(2) Uani 0.534(5) 1 d . U P A 2
H12' H 0.4269 0.8589 0.0406 0.059 Uiso 0.534(5) 1 calc R U P A 2
C13' C 0.437(2) 0.835(5) 0.0829(3) 0.048(2) Uani 0.534(5) 1 d . U P A 2
H13' H 0.5583 0.9323 0.0844 0.057 Uiso 0.534(5) 1 calc R U P A 2
N2' N 0.0832(10) 0.568(3) 0.0295(2) 0.050(3) Uani 0.534(5) 1 d . . P A 2
O1' O -0.1102(5) 0.3952(12) 0.03001(7) 0.0579(14) Uani 0.534(5) 1 d . . P A 2
H1' H -0.1044 0.2133 0.0214 0.087 Uiso 0.534(5) 1 calc R U P A 2
C15' C -0.1095(13) 0.387(3) 0.07508(19) 0.113(3) Uani 0.534(5) 1 d . . P A 2
H15D H -0.1980 0.5609 0.0689 0.169 Uiso 0.534(5) 1 calc R U P A 2
H15E H -0.1505 0.2913 0.0931 0.169 Uiso 0.534(5) 1 calc R U P A 2
H15F H -0.1059 0.2118 0.0606 0.169 Uiso 0.534(5) 1 calc R U P A 2
C14 C 0.6008(5) 0.9433(9) 0.13909(6) 0.0609(8) Uani 1 1 d . . . . .
N1 N 0.7489(4) 1.0762(9) 0.14005(7) 0.0809(9) 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 C6 1.396(4) . ?
C1 C2 1.398(4) . ?
C1 C7 1.474(4) . ?
C2 C3 1.361(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.390(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.35(2) . ?
C7 C8' 1.438(17) . ?
C7 C14 1.444(4) . ?
C8 C13 1.424(12) . ?
C8 C9 1.447(17) . ?
C9 C10 1.332(16) . ?
C9 H9 0.9300 . ?
C10 C11 1.427(10) . ?
C10 H10 0.9300 . ?
C11 N2 1.40(2) . ?
C11 C12 1.456(14) . ?
C12 C13 1.399(19) . ?
C12 C15 1.630(12) . ?
C13 H13 0.9300 . ?
N2 O1 1.622(18) . ?
O1 H1 0.8200 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C8' C9' 1.437(15) . ?
C8' C13' 1.462(10) . ?
C9' C10' 1.365(15) . ?
C9' H9' 0.9300 . ?
C10' C15' 1.396(15) . ?
C10' C11' 1.420(9) . ?
C11' N2' 1.282(17) . ?
C11' C12' 1.462(12) . ?
C12' C13' 1.305(15) . ?
C12' H12' 0.9300 . ?
C13' H13' 0.9300 . ?
N2' O1' 1.509(9) . ?
O1' H1' 0.8200 . ?
C15' H15D 0.9600 . ?
C15' H15E 0.9600 . ?
C15' H15F 0.9600 . ?
C14 N1 1.156(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
C6 C1 C2 118.0(3) . . ?
C6 C1 C7 121.7(3) . . ?
C2 C1 C7 120.3(3) . . ?
C3 C2 C1 121.7(4) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C2 C3 C4 119.9(4) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 119.7(4) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.6(4) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 120.1(3) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
C8 C7 C14 124.4(7) . . ?
C8' C7 C14 111.0(6) . . ?
C8 C7 C1 120.9(7) . . ?
C8' C7 C1 134.3(6) . . ?
C14 C7 C1 114.7(2) . . ?
C7 C8 C13 113.9(11) . . ?
C7 C8 C9 129.5(10) . . ?
C13 C8 C9 116.5(11) . . ?
C10 C9 C8 121.6(9) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C9 C10 C11 122.6(10) . . ?
C9 C10 H10 118.7 . . ?
C11 C10 H10 118.7 . . ?
N2 C11 C10 132.1(12) . . ?
N2 C11 C12 109.7(12) . . ?
C10 C11 C12 118.2(10) . . ?
C13 C12 C11 118.0(9) . . ?
C13 C12 C15 119.8(10) . . ?
C11 C12 C15 122.2(11) . . ?
C12 C13 C8 123.1(10) . . ?
C12 C13 H13 118.5 . . ?
C8 C13 H13 118.5 . . ?
C11 N2 O1 121.9(13) . . ?
N2 O1 H1 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C9' C8' C7 117.7(9) . . ?
C9' C8' C13' 115.6(9) . . ?
C7 C8' C13' 126.7(10) . . ?
C10' C9' C8' 122.4(8) . . ?
C10' C9' H9' 118.8 . . ?
C8' C9' H9' 118.8 . . ?
C9' C10' C15' 122.7(8) . . ?
C9' C10' C11' 119.5(9) . . ?
C15' C10' C11' 117.8(9) . . ?
N2' C11' C10' 114.9(9) . . ?
N2' C11' C12' 125.8(9) . . ?
C10' C11' C12' 119.4(8) . . ?
C13' C12' C11' 119.7(8) . . ?
C13' C12' H12' 120.2 . . ?
C11' C12' H12' 120.2 . . ?
C12' C13' C8' 123.4(9) . . ?
C12' C13' H13' 118.3 . . ?
C8' C13' H13' 118.3 . . ?
C11' N2' O1' 119.1(9) . . ?
N2' O1' H1' 109.5 . . ?
C10' C15' H15D 109.5 . . ?
C10' C15' H15E 109.5 . . ?
H15D C15' H15E 109.5 . . ?
C10' C15' H15F 109.5 . . ?
H15D C15' H15F 109.5 . . ?
H15E C15' H15F 109.5 . . ?
N1 C14 C7 177.2(4) . . ?

_refine_diff_density_max         0.345
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.063

_shelxl_version_number           2013-4

