# 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_xhj
_database_code_depnum_ccdc_archive 'CCDC 1437626'
_audit_update_record             
;
2015-11-18 deposited with the CCDC.
2016-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        3-(2'-hydroxybenzylidene)nopinone
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C2.37 H2.67 N0 O0.30'
_chemical_formula_weight         35.90

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   8.938(4)
_cell_length_b                   11.742(5)
_cell_length_c                   12.745(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1337.7(10)
_cell_formula_units_Z            27
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      299(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12714
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_sigmaI/netI    0.0244
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         29.40
_reflns_number_total             3703
_reflns_number_gt                3190
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0812P)²+0.0873P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2.2(13)
_refine_ls_number_reflns         3703
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.1280
_refine_ls_wR_factor_gt          0.1210
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C10 C 0.04493(16) 0.86492(11) 0.36392(10) 0.0318(3) Uani 1 1 d . . .
H10A H 0.1419 0.8936 0.3631 0.038 Uiso 1 1 calc R . .
O1 O 0.19446(12) 0.95510(10) 0.53147(9) 0.0429(3) Uani 1 1 d . . .
C2 C 0.05964(15) 0.93589(11) 0.53906(10) 0.0299(3) Uani 1 1 d . . .
C11 C -0.00538(16) 0.81763(11) 0.26390(10) 0.0318(3) Uani 1 1 d . . .
C6 C -0.18418(16) 0.84019(14) 0.48305(11) 0.0367(3) Uani 1 1 d . . .
H6A H -0.1900 0.7582 0.4910 0.044 Uiso 1 1 calc R . .
H6B H -0.2501 0.8622 0.4261 0.044 Uiso 1 1 calc R . .
O2 O 0.16350(16) 0.94643(12) 0.18723(9) 0.0568(4) Uani 1 1 d . . .
H2A H 0.1967 0.9665 0.1302 0.085 Uiso 1 1 calc R . .
C1 C -0.02474(15) 0.87396(11) 0.45635(10) 0.0305(3) Uani 1 1 d . . .
C12 C 0.06262(16) 0.86131(13) 0.17297(11) 0.0359(3) Uani 1 1 d . . .
C5 C -0.23530(17) 0.89733(14) 0.58418(12) 0.0399(3) Uani 1 1 d . . .
H5A H -0.3412 0.8866 0.6015 0.048 Uiso 1 1 calc R . .
C14 C -0.0762(2) 0.73043(15) 0.06651(13) 0.0469(4) Uani 1 1 d . . .
H14A H -0.1001 0.7014 0.0007 0.056 Uiso 1 1 calc R . .
C13 C 0.02610(19) 0.81824(14) 0.07473(11) 0.0417(3) Uani 1 1 d . . .
H13A H 0.0703 0.8484 0.0148 0.050 Uiso 1 1 calc R . .
C7 C -0.12494(18) 0.87437(14) 0.67559(11) 0.0400(3) Uani 1 1 d . . .
C3 C -0.03198(18) 0.97647(12) 0.62920(12) 0.0385(3) Uani 1 1 d . . .
H3A H 0.0191 1.0254 0.6802 0.046 Uiso 1 1 calc R . .
C16 C -0.10786(18) 0.72958(13) 0.25229(12) 0.0398(3) Uani 1 1 d . . .
H16A H -0.1539 0.6996 0.3116 0.048 Uiso 1 1 calc R . .
C4 C -0.1816(2) 1.02266(14) 0.58367(15) 0.0478(4) Uani 1 1 d . . .
H4A H -0.2363 1.0722 0.6309 0.057 Uiso 1 1 calc R . .
H4B H -0.1728 1.0559 0.5143 0.057 Uiso 1 1 calc R . .
C15 C -0.1433(2) 0.68526(14) 0.15467(13) 0.0466(4) Uani 1 1 d . . .
H15A H -0.2115 0.6258 0.1486 0.056 Uiso 1 1 calc R . .
C9 C -0.1914(3) 0.9072(2) 0.78228(14) 0.0654(6) Uani 1 1 d . . .
H9A H -0.2478 0.8444 0.8097 0.098 Uiso 1 1 calc R . .
H9B H -0.2558 0.9720 0.7739 0.098 Uiso 1 1 calc R . .
H9C H -0.1120 0.9259 0.8300 0.098 Uiso 1 1 calc R . .
C8 C -0.0493(2) 0.75901(16) 0.68407(15) 0.0545(5) Uani 1 1 d . . .
H8A H -0.1182 0.7048 0.7132 0.082 Uiso 1 1 calc R . .
H8B H 0.0368 0.7651 0.7288 0.082 Uiso 1 1 calc R . .
H8C H -0.0187 0.7342 0.6156 0.082 Uiso 1 1 calc R . .


_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
C10 C1 1.3367(19) . ?
C10 C11 1.4614(18) . ?
C10 H10A 0.9300 . ?
O1 C2 1.2298(18) . ?
C2 C1 1.4862(18) . ?
C2 C3 1.489(2) . ?
C11 C16 1.389(2) . ?
C11 C12 1.4056(19) . ?
C6 C1 1.518(2) . ?
C6 C5 1.523(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
O2 C12 1.358(2) . ?
O2 H2A 0.8200 . ?
C12 C13 1.389(2) . ?
C5 C4 1.548(2) . ?
C5 C7 1.550(2) . ?
C5 H5A 0.9800 . ?
C14 C15 1.380(3) . ?
C14 C13 1.382(2) . ?
C14 H14A 0.9300 . ?
C13 H13A 0.9300 . ?
C7 C8 1.518(2) . ?
C7 C9 1.533(2) . ?
C7 C3 1.574(2) . ?
C3 C4 1.555(3) . ?
C3 H3A 0.9800 . ?
C16 C15 1.385(2) . ?
C16 H16A 0.9300 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C15 H15A 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 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
C1 C10 C11 130.96(13) . . ?
C1 C10 H10A 114.5 . . ?
C11 C10 H10A 114.5 . . ?
O1 C2 C1 122.09(13) . . ?
O1 C2 C3 122.74(13) . . ?
C1 C2 C3 115.13(12) . . ?
C16 C11 C12 117.96(13) . . ?
C16 C11 C10 125.35(12) . . ?
C12 C11 C10 116.59(12) . . ?
C1 C6 C5 110.87(12) . . ?
C1 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C12 O2 H2A 109.5 . . ?
C10 C1 C2 115.31(12) . . ?
C10 C1 C6 127.90(12) . . ?
C2 C1 C6 116.44(12) . . ?
O2 C12 C13 122.98(13) . . ?
O2 C12 C11 116.44(12) . . ?
C13 C12 C11 120.58(13) . . ?
C6 C5 C4 108.79(13) . . ?
C6 C5 C7 111.62(13) . . ?
C4 C5 C7 88.34(13) . . ?
C6 C5 H5A 115.0 . . ?
C4 C5 H5A 115.0 . . ?
C7 C5 H5A 115.0 . . ?
C15 C14 C13 120.84(14) . . ?
C15 C14 H14A 119.6 . . ?
C13 C14 H14A 119.6 . . ?
C14 C13 C12 119.69(14) . . ?
C14 C13 H13A 120.2 . . ?
C12 C13 H13A 120.2 . . ?
C8 C7 C9 109.51(16) . . ?
C8 C7 C5 119.49(14) . . ?
C9 C7 C5 112.11(15) . . ?
C8 C7 C3 118.13(14) . . ?
C9 C7 C3 110.24(15) . . ?
C5 C7 C3 85.48(12) . . ?
C2 C3 C4 107.25(13) . . ?
C2 C3 C7 109.66(12) . . ?
C4 C3 C7 87.25(12) . . ?
C2 C3 H3A 116.3 . . ?
C4 C3 H3A 116.3 . . ?
C7 C3 H3A 116.3 . . ?
C15 C16 C11 121.74(15) . . ?
C15 C16 H16A 119.1 . . ?
C11 C16 H16A 119.1 . . ?
C5 C4 C3 86.19(12) . . ?
C5 C4 H4A 114.3 . . ?
C3 C4 H4A 114.3 . . ?
C5 C4 H4B 114.3 . . ?
C3 C4 H4B 114.3 . . ?
H4A C4 H4B 111.4 . . ?
C14 C15 C16 119.18(15) . . ?
C14 C15 H15A 120.4 . . ?
C16 C15 H15A 120.4 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        29.40
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.043
