# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_I_110K
_database_code_depnum_ccdc_archive 'CCDC 1401490'
#Added by publCIF




_audit_update_record             
;
2015-05-18 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;


_cell_special_details            ?
#Added by publCIF




_symmetry_space_group_name_hall  'P 2c -2n'
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
1-{3-[(2-Hydroxy-3-methoxy-benzylidene)-amino]-phenyl}-ethanone
_chemical_name_common            
1-{3-[(2-Hydroxy-3-methoxy-benzylidene)-amino]-phenyl}-ethanone
_chemical_melting_point          376
_chemical_formula_moiety         'C16 H15 N O3'
_chemical_formula_sum            'C16 H15 N O3'
_chemical_formula_weight         269.29

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           orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'

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

_cell_length_a                   19.0009(19)
_cell_length_b                   5.2814(9)
_cell_length_c                   25.611(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2570.1(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    110(1)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       rod
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.96
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1136
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           ?

_diffrn_ambient_temperature      110(1)
_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  'Oxford Diffraction Xcalibur Kappa CCD'
_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            10431
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_sigmaI/netI    0.0745
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         4.29
_diffrn_reflns_theta_max         27.00
_reflns_number_total             5260
_reflns_number_gt                3357
_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)+(0.0434P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_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   .
_refine_ls_number_reflns         5260
_refine_ls_number_parameters     367
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.0879
_refine_ls_wR_factor_gt          0.0822
_refine_ls_goodness_of_fit_ref   0.846
_refine_ls_restrained_S_all      0.846
_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
O11 O 0.39112(9) 0.1132(4) 0.21380(7) 0.0255(5) Uani 1 1 d . . .
H11 H 0.3641 -0.0007 0.2222 0.038 Uiso 1 1 calc R . .
O12 O 0.48975(9) 0.4597(4) 0.20557(7) 0.0266(5) Uani 1 1 d . . .
O13 O 0.09827(9) -0.2840(4) 0.40335(7) 0.0263(5) Uani 1 1 d . . .
N11 N 0.28936(11) -0.0891(4) 0.26896(8) 0.0191(5) Uani 1 1 d . . .
C11 C 0.35866(12) 0.2614(5) 0.29982(9) 0.0169(6) Uani 1 1 d . . .
C12 C 0.39989(13) 0.2738(5) 0.25465(10) 0.0173(6) Uani 1 1 d . . .
C13 C 0.45215(12) 0.4635(5) 0.25067(10) 0.0188(6) Uani 1 1 d . . .
C14 C 0.46132(13) 0.6326(5) 0.29101(10) 0.0190(6) Uani 1 1 d . . .
H14 H 0.4951 0.7592 0.2880 0.023 Uiso 1 1 calc R . .
C15 C 0.42063(12) 0.6169(5) 0.33645(11) 0.0204(6) Uani 1 1 d . . .
H15 H 0.4278 0.7299 0.3638 0.024 Uiso 1 1 calc R . .
C16 C 0.37008(12) 0.4328(5) 0.34016(10) 0.0197(6) Uani 1 1 d . . .
H16 H 0.3429 0.4222 0.3703 0.024 Uiso 1 1 calc R . .
C17 C 0.30271(12) 0.0749(5) 0.30455(10) 0.0193(6) Uani 1 1 d . . .
H17 H 0.2754 0.0745 0.3347 0.023 Uiso 1 1 calc R . .
C18 C 0.23366(12) -0.2674(5) 0.27611(10) 0.0189(6) Uani 1 1 d . . .
C19 C 0.18793(12) -0.2679(5) 0.31844(9) 0.0173(6) Uani 1 1 d . . .
H19 H 0.1921 -0.1441 0.3441 0.021 Uiso 1 1 calc R . .
C110 C 0.13602(13) -0.4522(5) 0.32270(9) 0.0175(6) Uani 1 1 d . . .
C111 C 0.12758(13) -0.6313(5) 0.28332(10) 0.0207(6) Uani 1 1 d . . .
H111 H 0.0923 -0.7527 0.2857 0.025 Uiso 1 1 calc R . .
C112 C 0.17201(13) -0.6275(5) 0.24059(10) 0.0228(6) Uani 1 1 d . . .
H112 H 0.1661 -0.7451 0.2139 0.027 Uiso 1 1 calc R . .
C113 C 0.22515(13) -0.4501(5) 0.23729(10) 0.0186(6) Uani 1 1 d . . .
H113 H 0.2556 -0.4524 0.2089 0.022 Uiso 1 1 calc R . .
C114 C 0.09141(12) -0.4504(5) 0.37094(10) 0.0182(6) Uani 1 1 d . . .
C115 C 0.03964(13) -0.6605(5) 0.37807(10) 0.0244(7) Uani 1 1 d . . .
H11A H 0.0644 -0.8170 0.3831 0.037 Uiso 1 1 calc R . .
H11B H 0.0104 -0.6731 0.3476 0.037 Uiso 1 1 calc R . .
H11C H 0.0108 -0.6263 0.4081 0.037 Uiso 1 1 calc R . .
C116 C 0.54116(13) 0.6588(6) 0.19896(11) 0.0275(7) Uani 1 1 d . . .
H11D H 0.5179 0.8201 0.1994 0.041 Uiso 1 1 calc R . .
H11E H 0.5650 0.6369 0.1662 0.041 Uiso 1 1 calc R . .
H11F H 0.5748 0.6516 0.2269 0.041 Uiso 1 1 calc R . .
O21 O 0.57742(9) 1.1066(4) 0.10888(7) 0.0249(4) Uani 1 1 d . . .
H21 H 0.5424 1.0193 0.1039 0.037 Uiso 1 1 calc R . .
O22 O 0.67991(9) 1.4350(4) 0.11644(7) 0.0247(5) Uani 1 1 d . . .
O23 O 0.28331(9) 0.7004(4) -0.07847(7) 0.0255(5) Uani 1 1 d . . .
N21 N 0.46955(10) 0.9326(4) 0.05726(8) 0.0189(5) Uani 1 1 d . . .
C21 C 0.53900(12) 1.2781(5) 0.02662(9) 0.0165(6) Uani 1 1 d . . .
C22 C 0.58412(12) 1.2739(5) 0.07013(9) 0.0171(6) Uani 1 1 d . . .
C23 C 0.63869(12) 1.4555(6) 0.07313(10) 0.0195(6) Uani 1 1 d . . .
C24 C 0.64670(13) 1.6323(5) 0.03419(10) 0.0200(6) Uani 1 1 d . . .
H24 H 0.6823 1.7526 0.0367 0.024 Uiso 1 1 calc R . .
C25 C 0.60212(13) 1.6336(5) -0.00907(10) 0.0214(6) Uani 1 1 d . . .
H25 H 0.6082 1.7534 -0.0353 0.026 Uiso 1 1 calc R . .
C26 C 0.54952(12) 1.4588(5) -0.01281(11) 0.0193(6) Uani 1 1 d . . .
H26 H 0.5202 1.4593 -0.0419 0.023 Uiso 1 1 calc R . .
C27 C 0.48072(13) 1.1028(5) 0.02290(10) 0.0179(6) Uani 1 1 d . . .
H27 H 0.4504 1.1146 -0.0055 0.022 Uiso 1 1 calc R . .
C28 C 0.41354(12) 0.7571(5) 0.05206(10) 0.0182(6) Uani 1 1 d . . .
C29 C 0.37142(12) 0.7380(5) 0.00758(10) 0.0176(6) Uani 1 1 d . . .
H29 H 0.3776 0.8517 -0.0198 0.021 Uiso 1 1 calc R . .
C210 C 0.32005(12) 0.5497(5) 0.00376(10) 0.0176(6) Uani 1 1 d . . .
C211 C 0.31051(13) 0.3818(5) 0.04492(10) 0.0205(6) Uani 1 1 d . . .
H211 H 0.2765 0.2557 0.0425 0.025 Uiso 1 1 calc R . .
C212 C 0.35141(13) 0.4013(6) 0.08959(10) 0.0229(6) Uani 1 1 d . . .
H212 H 0.3449 0.2893 0.1172 0.028 Uiso 1 1 calc R . .
C213 C 0.40224(12) 0.5897(5) 0.09274(10) 0.0190(6) Uani 1 1 d . . .
H213 H 0.4293 0.6036 0.1229 0.023 Uiso 1 1 calc R . .
C214 C 0.27761(13) 0.5363(5) -0.04518(11) 0.0187(6) Uani 1 1 d . . .
C215 C 0.22700(13) 0.3226(5) -0.05146(11) 0.0248(7) Uani 1 1 d . . .
H21A H 0.2020 0.3415 -0.0838 0.037 Uiso 1 1 calc R . .
H21B H 0.1941 0.3236 -0.0230 0.037 Uiso 1 1 calc R . .
H21C H 0.2523 0.1652 -0.0516 0.037 Uiso 1 1 calc R . .
C216 C 0.73148(13) 1.6246(5) 0.12282(11) 0.0267(7) Uani 1 1 d . . .
H21D H 0.7627 1.6235 0.0933 0.040 Uiso 1 1 calc R . .
H21E H 0.7579 1.5923 0.1541 0.040 Uiso 1 1 calc R . .
H21F H 0.7090 1.7870 0.1254 0.040 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
O11 C12 1.357(3) . ?
O12 C13 1.358(3) . ?
O12 C116 1.445(3) . ?
O13 C114 1.216(3) . ?
N11 C17 1.283(3) . ?
N11 C18 1.429(3) . ?
C11 C16 1.391(4) . ?
C11 C12 1.399(3) . ?
C11 C17 1.454(4) . ?
C12 C13 1.414(4) . ?
C13 C14 1.376(4) . ?
C14 C15 1.400(4) . ?
C15 C16 1.370(4) . ?
C18 C19 1.390(3) . ?
C18 C113 1.395(4) . ?
C19 C110 1.390(4) . ?
C110 C111 1.392(4) . ?
C110 C114 1.498(3) . ?
C111 C112 1.382(4) . ?
C112 C113 1.380(4) . ?
C114 C115 1.494(4) . ?
O21 C22 1.335(3) . ?
O22 C23 1.362(3) . ?
O22 C216 1.410(3) . ?
O23 C214 1.221(3) . ?
N21 C27 1.276(3) . ?
N21 C28 1.417(3) . ?
C21 C26 1.404(4) . ?
C21 C22 1.406(3) . ?
C21 C27 1.447(4) . ?
C22 C23 1.414(4) . ?
C23 C24 1.375(4) . ?
C24 C25 1.395(3) . ?
C25 C26 1.364(4) . ?
C28 C213 1.383(4) . ?
C28 C29 1.396(3) . ?
C29 C210 1.397(4) . ?
C210 C211 1.389(4) . ?
C210 C214 1.492(4) . ?
C211 C212 1.387(3) . ?
C212 C213 1.389(4) . ?
C214 C215 1.491(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
C13 O12 C116 116.4(2) . . ?
C17 N11 C18 120.0(2) . . ?
C16 C11 C12 119.8(2) . . ?
C16 C11 C17 119.5(2) . . ?
C12 C11 C17 120.7(2) . . ?
O11 C12 C11 122.7(2) . . ?
O11 C12 C13 118.3(2) . . ?
C11 C12 C13 119.1(2) . . ?
O12 C13 C14 125.5(2) . . ?
O12 C13 C12 114.8(2) . . ?
C14 C13 C12 119.6(2) . . ?
C13 C14 C15 121.0(2) . . ?
C16 C15 C14 119.1(3) . . ?
C15 C16 C11 121.3(3) . . ?
N11 C17 C11 122.9(2) . . ?
C19 C18 C113 118.9(2) . . ?
C19 C18 N11 124.4(2) . . ?
C113 C18 N11 116.8(2) . . ?
C18 C19 C110 120.4(2) . . ?
C19 C110 C111 120.1(2) . . ?
C19 C110 C114 117.5(2) . . ?
C111 C110 C114 122.4(2) . . ?
C112 C111 C110 119.6(3) . . ?
C113 C112 C111 120.3(3) . . ?
C112 C113 C18 120.7(2) . . ?
O13 C114 C115 121.6(2) . . ?
O13 C114 C110 120.4(2) . . ?
C115 C114 C110 117.9(2) . . ?
C23 O22 C216 115.9(2) . . ?
C27 N21 C28 121.4(2) . . ?
C26 C21 C22 119.6(2) . . ?
C26 C21 C27 119.8(2) . . ?
C22 C21 C27 120.6(2) . . ?
O21 C22 C21 122.8(2) . . ?
O21 C22 C23 118.6(2) . . ?
C21 C22 C23 118.6(2) . . ?
O22 C23 C24 125.5(2) . . ?
O22 C23 C22 114.3(2) . . ?
C24 C23 C22 120.2(2) . . ?
C23 C24 C25 120.8(2) . . ?
C26 C25 C24 119.8(3) . . ?
C25 C26 C21 120.9(3) . . ?
N21 C27 C21 122.2(2) . . ?
C213 C28 C29 118.6(2) . . ?
C213 C28 N21 117.6(2) . . ?
C29 C28 N21 123.7(2) . . ?
C28 C29 C210 120.6(2) . . ?
C211 C210 C29 119.5(2) . . ?
C211 C210 C214 122.4(2) . . ?
C29 C210 C214 118.1(2) . . ?
C212 C211 C210 120.4(2) . . ?
C211 C212 C213 119.4(3) . . ?
C28 C213 C212 121.5(2) . . ?
O23 C214 C215 121.3(2) . . ?
O23 C214 C210 120.3(2) . . ?
C215 C214 C210 118.4(2) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.044

#============================================================
_iucr_refine_instruction_details 
;

TITL I_110K in Pna2(1)
CELL  0.71073  19.0009   5.2814  25.6108   90.000   90.000   90.000
ZERR     8.00   0.0019   0.0009   0.0046    0.000    0.000    0.000
LATT  -1
SYMM  - X, - Y, 1/2 + Z
SYMM  1/2 - X, 1/2 + Y, 1/2 + Z
SYMM  1/2 + X, 1/2 - Y,   Z
SFAC  C    H    N    O
UNIT  128  120  8    24
MERG   2
OMIT    -4.00  54.00
OMIT     3   4 -11
OMIT     2   3 -17
OMIT     3   4 -10
OMIT     2   0  24
FMAP   2
PLAN   20
ACTA
BOND
LIST   4
L.S.   6
WGHT    0.043400
FVAR       4.81945
MOLE    1
O11   4    0.391118    0.113215    0.213797    11.00000    0.02440    0.02881 =
         0.02333   -0.00117    0.00313   -0.00928
AFIX 147
H11   2    0.364075   -0.000722    0.222196    11.00000   -1.50000
AFIX   0
O12   4    0.489750    0.459673    0.205569    11.00000    0.02336    0.03571 =
         0.02078    0.00039    0.00273   -0.01222
O13   4    0.098271   -0.283990    0.403351    11.00000    0.02468    0.02913 =
         0.02503   -0.00305    0.00751   -0.00441
N11   3    0.289364   -0.089079    0.268964    11.00000    0.01450    0.02204 =
         0.02082    0.00309   -0.00254   -0.00060
C11   1    0.358656    0.261447    0.299817    11.00000    0.01298    0.01708 =
         0.02054    0.00618   -0.00254    0.00194
C12   1    0.399890    0.273806    0.254651    11.00000    0.01592    0.01820 =
         0.01774    0.00010   -0.00405    0.00290
C13   1    0.452147    0.463507    0.250669    11.00000    0.01262    0.02451 =
         0.01935    0.00534    0.00091    0.00003
C14   1    0.461321    0.632554    0.291007    11.00000    0.01724    0.01661 =
         0.02306    0.00501   -0.00012   -0.00108
AFIX  43
H14   2    0.495089    0.759198    0.288020    11.00000   -1.20000
AFIX   0
C15   1    0.420627    0.616854    0.336450    11.00000    0.01693    0.02223 =
         0.02190    0.00038   -0.00265    0.00351
AFIX  43
H15   2    0.427812    0.729935    0.363771    11.00000   -1.20000
AFIX   0
C16   1    0.370081    0.432770    0.340163    11.00000    0.01521    0.02710 =
         0.01677    0.00525    0.00345    0.00403
AFIX  43
H16   2    0.342866    0.422175    0.370266    11.00000   -1.20000
AFIX   0
C17   1    0.302714    0.074885    0.304551    11.00000    0.01206    0.02568 =
         0.02028    0.00622    0.00350    0.00360
AFIX  43
H17   2    0.275433    0.074469    0.334700    11.00000   -1.20000
AFIX   0
C18   1    0.233662   -0.267443    0.276108    11.00000    0.01490    0.02030 =
         0.02142    0.00424   -0.00412    0.00421
C19   1    0.187927   -0.267850    0.318444    11.00000    0.01779    0.01767 =
         0.01659   -0.00015   -0.00169   -0.00117
AFIX  43
H19   2    0.192067   -0.144063    0.344087    11.00000   -1.20000
AFIX   0
C110  1    0.136018   -0.452194    0.322696    11.00000    0.01563    0.01911 =
         0.01764    0.00292   -0.00266    0.00236
C111  1    0.127577   -0.631300    0.283317    11.00000    0.01620    0.01948 =
         0.02651   -0.00030   -0.00423   -0.00039
AFIX  43
H111  2    0.092278   -0.752716    0.285739    11.00000   -1.20000
AFIX   0
C112  1    0.172012   -0.627488    0.240589    11.00000    0.02321    0.02283 =
         0.02245   -0.00282   -0.00383    0.00065
AFIX  43
H112  2    0.166065   -0.745087    0.213924    11.00000   -1.20000
AFIX   0
C113  1    0.225149   -0.450097    0.237294    11.00000    0.02039    0.01763 =
         0.01787    0.00095    0.00175    0.00344
AFIX  43
H113  2    0.255617   -0.452375    0.208878    11.00000   -1.20000
AFIX   0
C114  1    0.091407   -0.450414    0.370940    11.00000    0.01758    0.01989 =
         0.01722    0.00202   -0.00036    0.00383
C115  1    0.039637   -0.660469    0.378072    11.00000    0.02006    0.02652 =
         0.02652    0.00048    0.00191   -0.00702
AFIX 137
H11A  2    0.064397   -0.817002    0.383135    11.00000   -1.50000
H11B  2    0.010405   -0.673127    0.347611    11.00000   -1.50000
H11C  2    0.010841   -0.626263    0.408054    11.00000   -1.50000
AFIX   0
C116  1    0.541162    0.658803    0.198965    11.00000    0.01808    0.03591 =
         0.02854    0.00544    0.00493   -0.00754
AFIX 137
H11D  2    0.517895    0.820139    0.199369    11.00000   -1.50000
H11E  2    0.564982    0.636930    0.166217    11.00000   -1.50000
H11F  2    0.574758    0.651604    0.226922    11.00000   -1.50000
AFIX   0
MOLE    2
O21   4    0.577416    1.106574    0.108878    11.00000    0.02022    0.03145 =
         0.02303    0.00314   -0.00356   -0.00841
AFIX 147
H21   2    0.542377    1.019261    0.103864    11.00000   -1.50000
AFIX   0
O22   4    0.679907    1.435029    0.116442    11.00000    0.01769    0.03629 =
         0.02013    0.00043   -0.00329   -0.00982
O23   4    0.283305    0.700394   -0.078469    11.00000    0.02805    0.02482 =
         0.02369    0.00264   -0.00549   -0.00404
N21   3    0.469552    0.932581    0.057256    11.00000    0.01486    0.02129 =
         0.02044   -0.00224   -0.00110    0.00133
C21   1    0.539001    1.278119    0.026625    11.00000    0.01108    0.02084 =
         0.01748   -0.00102    0.00118    0.00318
C22   1    0.584117    1.273926    0.070131    11.00000    0.01173    0.02275 =
         0.01671   -0.00069    0.00291    0.00199
C23   1    0.638689    1.455470    0.073128    11.00000    0.01399    0.02578 =
         0.01882   -0.00140    0.00030    0.00170
C24   1    0.646698    1.632315    0.034191    11.00000    0.01248    0.02229 =
         0.02510   -0.00313    0.00270   -0.00205
AFIX  43
H24   2    0.682288    1.752571    0.036731    11.00000   -1.20000
AFIX   0
C25   1    0.602121    1.633644   -0.009070    11.00000    0.02107    0.02119 =
         0.02195    0.00495    0.00081    0.00352
AFIX  43
H25   2    0.608238    1.753425   -0.035298    11.00000   -1.20000
AFIX   0
C26   1    0.549522    1.458773   -0.012812    11.00000    0.01227    0.02347 =
         0.02230   -0.00035   -0.00069    0.00407
AFIX  43
H26   2    0.520222    1.459256   -0.041900    11.00000   -1.20000
AFIX   0
C27   1    0.480718    1.102800    0.022901    11.00000    0.01556    0.01951 =
         0.01874   -0.00419   -0.00200    0.00190
AFIX  43
H27   2    0.450374    1.114584   -0.005487    11.00000   -1.20000
AFIX   0
C28   1    0.413541    0.757119    0.052065    11.00000    0.01278    0.02159 =
         0.02019   -0.00314    0.00129    0.00138
C29   1    0.371420    0.738003    0.007580    11.00000    0.01355    0.02134 =
         0.01787    0.00094    0.00169    0.00188
AFIX  43
H29   2    0.377620    0.851677   -0.019769    11.00000   -1.20000
AFIX   0
C210  1    0.320048    0.549724    0.003763    11.00000    0.01449    0.01723 =
         0.02102   -0.00351    0.00287    0.00232
C211  1    0.310514    0.381813    0.044917    11.00000    0.01482    0.02025 =
         0.02653   -0.00009    0.00055   -0.00073
AFIX  43
H211  2    0.276521    0.255663    0.042498    11.00000   -1.20000
AFIX   0
C212  1    0.351412    0.401302    0.089587    11.00000    0.02096    0.02589 =
         0.02194    0.00666    0.00185    0.00341
AFIX  43
H212  2    0.344867    0.289252    0.117176    11.00000   -1.20000
AFIX   0
C213  1    0.402236    0.589689    0.092745    11.00000    0.01237    0.02297 =
         0.02152   -0.00230   -0.00298    0.00295
AFIX  43
H213  2    0.429270    0.603578    0.122881    11.00000   -1.20000
AFIX   0
C214  1    0.277607    0.536267   -0.045184    11.00000    0.01301    0.01753 =
         0.02552   -0.00203    0.00174    0.00014
C215  1    0.227004    0.322614   -0.051460    11.00000    0.02253    0.02720 =
         0.02478   -0.00189   -0.00371   -0.00235
AFIX 137
H21A  2    0.202017    0.341490   -0.083806    11.00000   -1.50000
H21B  2    0.194148    0.323599   -0.022986    11.00000   -1.50000
H21C  2    0.252270    0.165206   -0.051630    11.00000   -1.50000
AFIX   0
C216  1    0.731483    1.624598    0.122823    11.00000    0.02137    0.03261 =
         0.02621   -0.00737   -0.00094   -0.00319
AFIX 137
H21D  2    0.762652    1.623542    0.093323    11.00000   -1.50000
H21E  2    0.757863    1.592311    0.154090    11.00000   -1.50000
H21F  2    0.709036    1.786965    0.125398    11.00000   -1.50000
HKLF    4
 
REM  I_110K in Pna2(1)
REM R1 =  0.0414 for   3357 Fo > 4sig(Fo)  and  0.0699 for all   5260 data
REM    367 parameters refined using      1 restraints
 
END  
     
WGHT      0.0434      0.0000 
REM Highest difference peak  0.221,  deepest hole -0.193,  1-sigma level  0.044
Q1    1   0.1987 -0.0958  0.3619  11.00000  0.05    0.22
Q2    1   0.3762  0.9001 -0.0364  11.00000  0.05    0.22
Q3    1   0.4082  0.4604  0.3428  11.00000  0.05    0.18
Q4    1   0.2942 -0.0257  0.2392  11.00000  0.05    0.18
Q5    1   0.0250 -0.7843  0.3371  11.00000  0.05    0.17
Q6    1   0.3332 -0.0976  0.2294  11.00000  0.05    0.17
Q7    1   0.3614  0.5463  0.0988  11.00000  0.05    0.17
Q8    1   0.7079  1.8276  0.0476  11.00000  0.05    0.17
Q9    1   0.2486 -0.1015  0.3105  11.00000  0.05    0.17
Q10   1   0.3892  0.2200  0.2855  11.00000  0.05    0.17
Q11   1   0.1946 -0.2221  0.2911  11.00000  0.05    0.16
Q12   1   0.5940  1.4473  0.0752  11.00000  0.05    0.16
Q13   1   0.4691  0.4697  0.2844  11.00000  0.05    0.16
Q14   1   0.5144  0.9091  0.0977  11.00000  0.05    0.16
Q15   1   0.6765  1.3128  0.1487  11.00000  0.05    0.16
Q16   1   0.4207  0.4033  0.2500  11.00000  0.05    0.16
Q17   1   0.3129  0.5003  0.0795  11.00000  0.05    0.15
Q18   1   0.6513  1.4940  0.0507  11.00000  0.05    0.15
Q19   1   0.4278  0.4610  0.3889  11.00000  0.05    0.15
Q20   1   0.3274  0.4094  0.0118  11.00000  0.05    0.15

;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
_chemical_properties_physical    Thermochromic
####################################################################### 
# 
# 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_I_200K
_database_code_depnum_ccdc_archive 'CCDC 1401491'
#Added by publCIF



_audit_update_record             
;
2015-05-18 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;


_symmetry_space_group_name_hall  'P 2c -2n'
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
1-{3-[(2-Hydroxy-3-methoxy-benzylidene)-amino]-phenyl}-ethanone
_chemical_name_common            
1-{3-[(2-Hydroxy-3-methoxy-benzylidene)-amino]-phenyl}-ethanone
_chemical_melting_point          376
_chemical_formula_moiety         'C16 H15 N O3'
_chemical_formula_sum            'C16 H15 N O3'
_chemical_formula_weight         269.29

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           orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'

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

_cell_length_a                   19.139(3)
_cell_length_b                   5.3140(13)
_cell_length_c                   26.000(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2644.3(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       rod
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.96
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1136
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           ?

_diffrn_ambient_temperature      200(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  'Oxford Diffraction Xcalibur Kappa CCD'
_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            16801
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_sigmaI/netI    0.0622
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         4.28
_diffrn_reflns_theta_max         27.00
_reflns_number_total             5701
_reflns_number_gt                3669
_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)+(0.2000P)²+0.0000P] 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   .
_refine_ls_number_reflns         5701
_refine_ls_number_parameters     372
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.1265
_refine_ls_R_factor_gt           0.0996
_refine_ls_wR_factor_ref         0.2945
_refine_ls_wR_factor_gt          0.2809
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O11 O 0.3882(2) 0.1170(9) 0.21489(16) 0.0452(11) Uani 1 1 d D . .
H11 H 0.362(3) -0.030(7) 0.217(2) 0.041(17) Uiso 1 1 d D . .
O12 O 0.4867(2) 0.4593(10) 0.20608(16) 0.0502(12) Uani 1 1 d . . .
O13 O 0.0987(2) -0.2917(9) 0.40287(16) 0.0461(11) Uani 1 1 d . . .
N11 N 0.2870(3) -0.0822(8) 0.26900(17) 0.0313(10) Uani 1 1 d . . .
C11 C 0.3561(3) 0.2621(11) 0.30024(19) 0.0305(12) Uani 1 1 d . . .
C12 C 0.3972(3) 0.2773(11) 0.2552(2) 0.0293(12) Uani 1 1 d D . .
C13 C 0.4488(3) 0.4611(10) 0.2519(2) 0.0303(12) Uani 1 1 d . . .
C14 C 0.4576(3) 0.6320(10) 0.2918(2) 0.0326(12) Uani 1 1 d . . .
H14 H 0.4915 0.7620 0.2889 0.039 Uiso 1 1 calc R . .
C15 C 0.4173(3) 0.6135(11) 0.3360(2) 0.0358(13) Uani 1 1 d . . .
H15 H 0.4244 0.7274 0.3637 0.043 Uiso 1 1 calc R . .
C16 C 0.3674(3) 0.4321(11) 0.3396(2) 0.0349(13) Uani 1 1 d . . .
H16 H 0.3397 0.4220 0.3698 0.042 Uiso 1 1 calc R . .
C17 C 0.3004(3) 0.0811(11) 0.3046(2) 0.0319(12) Uani 1 1 d . . .
H17 H 0.2724 0.0815 0.3348 0.038 Uiso 1 1 calc R . .
C18 C 0.2309(3) -0.2620(10) 0.27622(19) 0.0292(12) Uani 1 1 d . . .
C19 C 0.1864(3) -0.2711(10) 0.31884(18) 0.0266(11) Uani 1 1 d . . .
H19 H 0.1919 -0.1515 0.3457 0.032 Uiso 1 1 calc R . .
C110 C 0.1346(3) -0.4511(10) 0.3225(2) 0.0297(11) Uani 1 1 d U . .
C111 C 0.1255(3) -0.6272(11) 0.2831(2) 0.0340(13) Uani 1 1 d . . .
H111 H 0.0904 -0.7529 0.2857 0.041 Uiso 1 1 calc R . .
C112 C 0.1689(3) -0.6159(11) 0.2398(2) 0.0373(13) Uani 1 1 d . . .
H112 H 0.1619 -0.7304 0.2122 0.045 Uiso 1 1 calc R . .
C113 C 0.2230(3) -0.4360(11) 0.2367(2) 0.0352(13) Uani 1 1 d . . .
H113 H 0.2537 -0.4338 0.2080 0.042 Uiso 1 1 calc R . .
C114 C 0.0908(3) -0.4538(11) 0.3700(2) 0.0372(13) Uani 1 1 d U . .
C115 C 0.0401(3) -0.6668(12) 0.3781(3) 0.0428(15) Uani 1 1 d . . .
H11A H 0.0659 -0.8251 0.3816 0.064 Uiso 1 1 calc R . .
H11B H 0.0085 -0.6779 0.3485 0.064 Uiso 1 1 calc R . .
H11C H 0.0129 -0.6361 0.4094 0.064 Uiso 1 1 calc R . .
C116 C 0.5371(3) 0.6586(12) 0.1999(2) 0.0442(15) Uani 1 1 d . . .
H11D H 0.5143 0.8213 0.2057 0.066 Uiso 1 1 calc R . .
H11E H 0.5563 0.6535 0.1650 0.066 Uiso 1 1 calc R . .
H11F H 0.5749 0.6365 0.2249 0.066 Uiso 1 1 calc R . .
O21 O 0.5738(2) 1.1078(7) 0.10819(15) 0.0402(10) Uani 1 1 d D . .
O22 O 0.6751(2) 1.4377(9) 0.11559(16) 0.0456(12) Uani 1 1 d . . .
O23 O 0.2829(2) 0.6932(8) -0.07769(16) 0.0433(11) Uani 1 1 d . . .
N21 N 0.4668(2) 0.9343(8) 0.05677(17) 0.0325(11) Uani 1 1 d . . .
C21 C 0.5364(3) 1.2759(10) 0.0263(2) 0.0274(11) Uani 1 1 d . . .
C22 C 0.5807(3) 1.2730(10) 0.06976(18) 0.0276(11) Uani 1 1 d . . .
C23 C 0.6351(3) 1.4566(11) 0.07285(19) 0.0313(12) Uani 1 1 d . . .
C24 C 0.6445(3) 1.6324(11) 0.0344(2) 0.0339(12) Uani 1 1 d . . .
H24 H 0.6808 1.7537 0.0369 0.041 Uiso 1 1 calc R . .
C25 C 0.5998(3) 1.6305(11) -0.0087(2) 0.0347(13) Uani 1 1 d . . .
H25 H 0.6059 1.7525 -0.0350 0.042 Uiso 1 1 calc R . .
C26 C 0.5475(3) 1.4547(9) -0.0132(2) 0.0308(12) Uani 1 1 d . . .
H26 H 0.5186 1.4533 -0.0429 0.037 Uiso 1 1 calc R . .
C27 C 0.4787(3) 1.1015(9) 0.0223(2) 0.0287(11) Uani 1 1 d . . .
H27 H 0.4487 1.1110 -0.0067 0.034 Uiso 1 1 calc R . .
C28 C 0.4114(3) 0.7579(11) 0.05199(19) 0.0308(12) Uani 1 1 d . . .
C29 C 0.3696(3) 0.7379(9) 0.0079(2) 0.0260(11) Uani 1 1 d . . .
H29 H 0.3758 0.8538 -0.0195 0.031 Uiso 1 1 calc R . .
C210 C 0.3195(3) 0.5516(9) 0.0039(2) 0.0286(11) Uani 1 1 d . . .
C211 C 0.3089(3) 0.3853(10) 0.0450(2) 0.0338(13) Uani 1 1 d . . .
H211 H 0.2743 0.2576 0.0426 0.041 Uiso 1 1 calc R . .
C212 C 0.3489(3) 0.4077(11) 0.0892(2) 0.0381(14) Uani 1 1 d . . .
H212 H 0.3418 0.2950 0.1170 0.046 Uiso 1 1 calc R . .
C213 C 0.3989(3) 0.5930(10) 0.0926(2) 0.0347(13) Uani 1 1 d . . .
H213 H 0.4255 0.6088 0.1233 0.042 Uiso 1 1 calc R . .
C214 C 0.2771(3) 0.5295(10) -0.0446(2) 0.0324(12) Uani 1 1 d . . .
C215 C 0.2267(3) 0.3216(11) -0.0507(2) 0.0413(14) Uani 1 1 d . . .
H21A H 0.2040 0.3344 -0.0843 0.062 Uiso 1 1 calc R . .
H21B H 0.1913 0.3320 -0.0235 0.062 Uiso 1 1 calc R . .
H21C H 0.2513 0.1604 -0.0481 0.062 Uiso 1 1 calc R . .
C216 C 0.7266(4) 1.6234(12) 0.1221(2) 0.0484(16) Uani 1 1 d . . .
H21D H 0.7570 1.6272 0.0918 0.073 Uiso 1 1 calc R . .
H21E H 0.7546 1.5847 0.1527 0.073 Uiso 1 1 calc R . .
H21F H 0.7042 1.7879 0.1265 0.073 Uiso 1 1 calc R . .
H21 H 0.532(2) 1.006(12) 0.105(3) 0.058 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
O11 C12 1.361(7) . ?
O11 H11 0.936(19) . ?
O12 C13 1.394(7) . ?
O12 C116 1.442(7) . ?
O13 C114 1.224(7) . ?
N11 C17 1.295(7) . ?
N11 C18 1.451(7) . ?
C11 C16 1.381(8) . ?
C11 C12 1.414(7) . ?
C11 C17 1.440(7) . ?
C12 C13 1.392(8) . ?
C13 C14 1.390(8) . ?
C14 C15 1.387(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.360(8) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C113 1.391(8) . ?
C18 C19 1.398(7) . ?
C19 C110 1.381(7) . ?
C19 H19 0.9500 . ?
C110 C111 1.397(7) . ?
C110 C114 1.492(8) . ?
C111 C112 1.402(8) . ?
C111 H111 0.9500 . ?
C112 C113 1.411(8) . ?
C112 H112 0.9500 . ?
C113 H113 0.9500 . ?
C114 C115 1.506(8) . ?
C115 H11A 0.9800 . ?
C115 H11B 0.9800 . ?
C115 H11C 0.9800 . ?
C116 H11D 0.9800 . ?
C116 H11E 0.9800 . ?
C116 H11F 0.9800 . ?
O21 C22 1.336(6) . ?
O21 H21 0.97(2) . ?
O22 C23 1.354(7) . ?
O22 C216 1.405(7) . ?
O23 C214 1.228(7) . ?
N21 C27 1.282(7) . ?
N21 C28 1.421(7) . ?
C21 C22 1.413(7) . ?
C21 C26 1.414(7) . ?
C21 C27 1.445(7) . ?
C22 C23 1.429(8) . ?
C23 C24 1.380(8) . ?
C24 C25 1.409(9) . ?
C24 H24 0.9500 . ?
C25 C26 1.374(8) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C213 1.393(8) . ?
C28 C29 1.402(7) . ?
C29 C210 1.382(7) . ?
C29 H29 0.9500 . ?
C210 C211 1.403(7) . ?
C210 C214 1.504(8) . ?
C211 C212 1.385(9) . ?
C211 H211 0.9500 . ?
C212 C213 1.377(9) . ?
C212 H212 0.9500 . ?
C213 H213 0.9500 . ?
C214 C215 1.475(8) . ?
C215 H21A 0.9800 . ?
C215 H21B 0.9800 . ?
C215 H21C 0.9800 . ?
C216 H21D 0.9800 . ?
C216 H21E 0.9800 . ?
C216 H21F 0.9800 . ?

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
C12 O11 H11 124(3) . . ?
C13 O12 C116 115.9(4) . . ?
C17 N11 C18 119.7(4) . . ?
C16 C11 C12 119.3(5) . . ?
C16 C11 C17 119.6(5) . . ?
C12 C11 C17 121.0(5) . . ?
O11 C12 C13 118.8(5) . . ?
O11 C12 C11 122.1(5) . . ?
C13 C12 C11 119.1(5) . . ?
C14 C13 C12 119.9(5) . . ?
C14 C13 O12 125.5(5) . . ?
C12 C13 O12 114.6(5) . . ?
C15 C14 C13 120.3(5) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 119.8(6) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C11 121.5(5) . . ?
C15 C16 H16 119.2 . . ?
C11 C16 H16 119.2 . . ?
N11 C17 C11 122.5(5) . . ?
N11 C17 H17 118.8 . . ?
C11 C17 H17 118.8 . . ?
C113 C18 C19 119.8(5) . . ?
C113 C18 N11 115.0(5) . . ?
C19 C18 N11 125.2(5) . . ?
C110 C19 C18 121.0(5) . . ?
C110 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C19 C110 C111 120.2(5) . . ?
C19 C110 C114 117.8(5) . . ?
C111 C110 C114 122.0(5) . . ?
C110 C111 C112 119.1(5) . . ?
C110 C111 H111 120.5 . . ?
C112 C111 H111 120.5 . . ?
C111 C112 C113 120.7(5) . . ?
C111 C112 H112 119.7 . . ?
C113 C112 H112 119.7 . . ?
C18 C113 C112 119.2(5) . . ?
C18 C113 H113 120.4 . . ?
C112 C113 H113 120.4 . . ?
O13 C114 C110 120.2(5) . . ?
O13 C114 C115 120.7(5) . . ?
C110 C114 C115 119.0(5) . . ?
C114 C115 H11A 109.5 . . ?
C114 C115 H11B 109.5 . . ?
H11A C115 H11B 109.5 . . ?
C114 C115 H11C 109.5 . . ?
H11A C115 H11C 109.5 . . ?
H11B C115 H11C 109.5 . . ?
O12 C116 H11D 109.5 . . ?
O12 C116 H11E 109.5 . . ?
H11D C116 H11E 109.5 . . ?
O12 C116 H11F 109.5 . . ?
H11D C116 H11F 109.5 . . ?
H11E C116 H11F 109.5 . . ?
C22 O21 H21 113(5) . . ?
C23 O22 C216 116.4(5) . . ?
C27 N21 C28 121.9(5) . . ?
C22 C21 C26 119.9(5) . . ?
C22 C21 C27 120.5(4) . . ?
C26 C21 C27 119.6(5) . . ?
O21 C22 C21 123.1(5) . . ?
O21 C22 C23 118.6(5) . . ?
C21 C22 C23 118.3(4) . . ?
O22 C23 C24 124.8(5) . . ?
O22 C23 C22 114.1(5) . . ?
C24 C23 C22 121.1(5) . . ?
C23 C24 C25 119.4(5) . . ?
C23 C24 H24 120.3 . . ?
C25 C24 H24 120.3 . . ?
C26 C25 C24 121.0(5) . . ?
C26 C25 H25 119.5 . . ?
C24 C25 H25 119.5 . . ?
C25 C26 C21 120.3(5) . . ?
C25 C26 H26 119.9 . . ?
C21 C26 H26 119.9 . . ?
N21 C27 C21 122.1(5) . . ?
N21 C27 H27 119.0 . . ?
C21 C27 H27 119.0 . . ?
C213 C28 C29 118.4(5) . . ?
C213 C28 N21 118.4(5) . . ?
C29 C28 N21 123.2(5) . . ?
C210 C29 C28 120.8(5) . . ?
C210 C29 H29 119.6 . . ?
C28 C29 H29 119.6 . . ?
C29 C210 C211 119.6(5) . . ?
C29 C210 C214 119.6(5) . . ?
C211 C210 C214 120.8(5) . . ?
C212 C211 C210 119.9(5) . . ?
C212 C211 H211 120.1 . . ?
C210 C211 H211 120.1 . . ?
C213 C212 C211 120.1(5) . . ?
C213 C212 H212 120.0 . . ?
C211 C212 H212 120.0 . . ?
C212 C213 C28 121.2(5) . . ?
C212 C213 H213 119.4 . . ?
C28 C213 H213 119.4 . . ?
O23 C214 C215 121.0(5) . . ?
O23 C214 C210 118.9(5) . . ?
C215 C214 C210 120.0(5) . . ?
C214 C215 H21A 109.5 . . ?
C214 C215 H21B 109.5 . . ?
H21A C215 H21B 109.5 . . ?
C214 C215 H21C 109.5 . . ?
H21A C215 H21C 109.5 . . ?
H21B C215 H21C 109.5 . . ?
O22 C216 H21D 109.5 . . ?
O22 C216 H21E 109.5 . . ?
H21D C216 H21E 109.5 . . ?
O22 C216 H21F 109.5 . . ?
H21D C216 H21F 109.5 . . ?
H21E C216 H21F 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
C16 C11 C12 O11 -179.4(5) . . . . ?
C17 C11 C12 O11 -2.6(8) . . . . ?
C16 C11 C12 C13 1.0(8) . . . . ?
C17 C11 C12 C13 177.7(5) . . . . ?
O11 C12 C13 C14 178.0(5) . . . . ?
C11 C12 C13 C14 -2.3(8) . . . . ?
O11 C12 C13 O12 -0.1(7) . . . . ?
C11 C12 C13 O12 179.6(5) . . . . ?
C116 O12 C13 C14 -2.3(8) . . . . ?
C116 O12 C13 C12 175.7(5) . . . . ?
C12 C13 C14 C15 2.8(8) . . . . ?
O12 C13 C14 C15 -179.3(5) . . . . ?
C13 C14 C15 C16 -2.0(8) . . . . ?
C14 C15 C16 C11 0.6(8) . . . . ?
C12 C11 C16 C15 -0.1(8) . . . . ?
C17 C11 C16 C15 -176.9(5) . . . . ?
C18 N11 C17 C11 179.0(5) . . . . ?
C16 C11 C17 N11 179.7(5) . . . . ?
C12 C11 C17 N11 3.0(8) . . . . ?
C17 N11 C18 C113 -177.2(5) . . . . ?
C17 N11 C18 C19 2.4(8) . . . . ?
C113 C18 C19 C110 0.2(8) . . . . ?
N11 C18 C19 C110 -179.5(5) . . . . ?
C18 C19 C110 C111 -0.4(8) . . . . ?
C18 C19 C110 C114 177.9(5) . . . . ?
C19 C110 C111 C112 -0.9(8) . . . . ?
C114 C110 C111 C112 -179.2(5) . . . . ?
C110 C111 C112 C113 2.6(9) . . . . ?
C19 C18 C113 C112 1.5(8) . . . . ?
N11 C18 C113 C112 -178.9(5) . . . . ?
C111 C112 C113 C18 -2.9(9) . . . . ?
C19 C110 C114 O13 4.1(8) . . . . ?
C111 C110 C114 O13 -177.6(6) . . . . ?
C19 C110 C114 C115 -172.4(5) . . . . ?
C111 C110 C114 C115 5.9(8) . . . . ?
C26 C21 C22 O21 -179.3(5) . . . . ?
C27 C21 C22 O21 2.3(8) . . . . ?
C26 C21 C22 C23 1.2(7) . . . . ?
C27 C21 C22 C23 -177.3(5) . . . . ?
C216 O22 C23 C24 4.6(8) . . . . ?
C216 O22 C23 C22 -176.1(5) . . . . ?
O21 C22 C23 O22 1.0(7) . . . . ?
C21 C22 C23 O22 -179.5(4) . . . . ?
O21 C22 C23 C24 -179.7(5) . . . . ?
C21 C22 C23 C24 -0.1(7) . . . . ?
O22 C23 C24 C25 179.1(5) . . . . ?
C22 C23 C24 C25 -0.1(8) . . . . ?
C23 C24 C25 C26 -0.6(8) . . . . ?
C24 C25 C26 C21 1.7(8) . . . . ?
C22 C21 C26 C25 -2.0(7) . . . . ?
C27 C21 C26 C25 176.5(5) . . . . ?
C28 N21 C27 C21 -178.0(5) . . . . ?
C22 C21 C27 N21 -2.2(8) . . . . ?
C26 C21 C27 N21 179.3(5) . . . . ?
C27 N21 C28 C213 -175.8(5) . . . . ?
C27 N21 C28 C29 5.7(8) . . . . ?
C213 C28 C29 C210 -3.0(7) . . . . ?
N21 C28 C29 C210 175.5(5) . . . . ?
C28 C29 C210 C211 2.0(8) . . . . ?
C28 C29 C210 C214 -178.0(5) . . . . ?
C29 C210 C211 C212 -0.5(8) . . . . ?
C214 C210 C211 C212 179.5(5) . . . . ?
C210 C211 C212 C213 0.1(8) . . . . ?
C211 C212 C213 C28 -1.2(8) . . . . ?
C29 C28 C213 C212 2.7(8) . . . . ?
N21 C28 C213 C212 -176.0(5) . . . . ?
C29 C210 C214 O23 -7.3(8) . . . . ?
C211 C210 C214 O23 172.8(5) . . . . ?
C29 C210 C214 C215 176.1(5) . . . . ?
C211 C210 C214 C215 -3.9(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.117

#============================================================
_iucr_refine_instruction_details 
;

TITL I_200K in Pna2(1)
CELL  0.71073  19.1390   5.3140  26.0000   90.000   90.000   90.000
ZERR     8.00   0.0030   0.0013   0.0050    0.000    0.000    0.000
LATT  -1
SYMM  - X, - Y, 1/2 + Z
SYMM  1/2 - X, 1/2 + Y, 1/2 + Z
SYMM  1/2 + X, 1/2 - Y,   Z
SFAC  C    H    N    O
UNIT  128  120  8    24
MERG   2
OMIT    -4.00  54.00
OMIT     8   1   0
OMIT     3   2  -2
OMIT     3   2   2
OMIT     2   0  24
dfix  0.95  O21  H21
dfix  0.95  O11  H11
dang  1.95  C12  H11
delu 0.001  0.001  C110  C114
FMAP   2
PLAN   20
ACTA
BOND
bond  $H
CONF
LIST   4
L.S.   6
TEMP   -73.00
WGHT    0.200000
FVAR       5.03629
MOLE    1
O11   4    0.388216    0.116958    0.214885    11.00000    0.04044    0.05658 =
         0.03845   -0.00140    0.01016   -0.02070
H11   2    0.361503   -0.030240    0.216659    11.00000    0.04054
O12   4    0.486675    0.459289    0.206082    11.00000    0.04551    0.07085 =
         0.03411   -0.00378    0.00657   -0.02663
O13   4    0.098663   -0.291664    0.402867    11.00000    0.04611    0.04696 =
         0.04534   -0.01151    0.01964   -0.01159
N11   3    0.287043   -0.082220    0.269002    11.00000    0.02990    0.03550 =
         0.02847    0.00328    0.00338   -0.00310
C11   1    0.356112    0.262097    0.300241    11.00000    0.02421    0.04037 =
         0.02681    0.01028   -0.00227   -0.00451
C12   1    0.397216    0.277283    0.255174    11.00000    0.02001    0.03906 =
         0.02892    0.00270   -0.00041    0.00456
C13   1    0.448841    0.461137    0.251878    11.00000    0.02873    0.02832 =
         0.03373    0.00431    0.00328    0.00565
C14   1    0.457632    0.631951    0.291832    11.00000    0.03081    0.02618 =
         0.04078    0.01091    0.00359    0.00064
AFIX  43
H14   2    0.491462    0.761979    0.288893    11.00000   -1.20000
AFIX   0
C15   1    0.417255    0.613547    0.335985    11.00000    0.03378    0.02943 =
         0.04421    0.00191   -0.00368    0.00157
AFIX  43
H15   2    0.424424    0.727428    0.363652    11.00000   -1.20000
AFIX   0
C16   1    0.367380    0.432061    0.339566    11.00000    0.02341    0.04940 =
         0.03203    0.00847   -0.00212    0.00356
AFIX  43
H16   2    0.339661    0.421973    0.369806    11.00000   -1.20000
AFIX   0
C17   1    0.300425    0.081107    0.304633    11.00000    0.02408    0.04496 =
         0.02678    0.00630    0.00496   -0.00103
AFIX  43
H17   2    0.272446    0.081543    0.334814    11.00000   -1.20000
AFIX   0
C18   1    0.230870   -0.262028    0.276220    11.00000    0.02535    0.02842 =
         0.03376    0.00122   -0.00301    0.00526
C19   1    0.186371   -0.271074    0.318839    11.00000    0.02653    0.03071 =
         0.02243   -0.00087    0.00129    0.00107
AFIX  43
H19   2    0.191856   -0.151550    0.345709    11.00000   -1.20000
AFIX   0
C110  1    0.134570   -0.451139    0.322458    11.00000    0.02347    0.03167 =
         0.03405    0.00034   -0.00454    0.00011
C111  1    0.125503   -0.627208    0.283124    11.00000    0.03324    0.04092 =
         0.02795   -0.00318    0.00066   -0.00874
AFIX  43
H111  2    0.090383   -0.752905    0.285714    11.00000   -1.20000
AFIX   0
C112  1    0.168936   -0.615851    0.239788    11.00000    0.04261    0.03617 =
         0.03305   -0.01022    0.00014   -0.00966
AFIX  43
H112  2    0.161891   -0.730390    0.212217    11.00000   -1.20000
AFIX   0
C113  1    0.223029   -0.436013    0.236686    11.00000    0.03835    0.03937 =
         0.02794    0.00213    0.00532   -0.00648
AFIX  43
H113  2    0.253695   -0.433836    0.207958    11.00000   -1.20000
AFIX   0
C114  1    0.090837   -0.453832    0.369960    11.00000    0.04818    0.03540 =
         0.02800    0.00036    0.00040    0.00024
C115  1    0.040120   -0.666818    0.378052    11.00000    0.03215    0.05011 =
         0.04626    0.00002    0.00114   -0.01421
AFIX 137
H11A  2    0.065938   -0.825135    0.381588    11.00000   -1.50000
H11B  2    0.008516   -0.677878    0.348482    11.00000   -1.50000
H11C  2    0.012900   -0.636055    0.409352    11.00000   -1.50000
AFIX   0
C116  1    0.537088    0.658622    0.199941    11.00000    0.04048    0.04879 =
         0.04327    0.01044    0.01339   -0.01705
AFIX 137
H11D  2    0.514293    0.821326    0.205714    11.00000   -1.50000
H11E  2    0.556297    0.653518    0.165018    11.00000   -1.50000
H11F  2    0.574942    0.636522    0.224918    11.00000   -1.50000
AFIX   0
MOLE    2
O21   4    0.573776    1.107829    0.108190    11.00000    0.04238    0.04746 =
         0.03063    0.00691   -0.00883   -0.01392
O22   4    0.675136    1.437712    0.115589    11.00000    0.03512    0.06807 =
         0.03362   -0.00504   -0.00814   -0.02232
O23   4    0.282895    0.693170   -0.077688    11.00000    0.05276    0.04109 =
         0.03619    0.00377   -0.01226   -0.01690
N21   3    0.466810    0.934278    0.056769    11.00000    0.02627    0.03372 =
         0.03738   -0.00219    0.00142   -0.00106
C21   1    0.536414    1.275938    0.026278    11.00000    0.02327    0.02566 =
         0.03334    0.00089    0.00316    0.00434
C22   1    0.580680    1.272977    0.069757    11.00000    0.03072    0.02784 =
         0.02434   -0.00256    0.00634   -0.00490
C23   1    0.635093    1.456576    0.072853    11.00000    0.02542    0.04423 =
         0.02411   -0.00403    0.00630   -0.00019
C24   1    0.644496    1.632377    0.034402    11.00000    0.02785    0.03794 =
         0.03585   -0.00636    0.00844   -0.01228
AFIX  43
H24   2    0.680797    1.753668    0.036945    11.00000   -1.20000
AFIX   0
C25   1    0.599792    1.630450   -0.008670    11.00000    0.03326    0.03603 =
         0.03494    0.00770   -0.00039    0.00169
AFIX  43
H25   2    0.605913    1.752473   -0.034991    11.00000   -1.20000
AFIX   0
C26   1    0.547485    1.454694   -0.013159    11.00000    0.03150    0.02494 =
         0.03595    0.00124   -0.00361    0.00798
AFIX  43
H26   2    0.518637    1.453298   -0.042892    11.00000   -1.20000
AFIX   0
C27   1    0.478729    1.101479    0.022341    11.00000    0.02472    0.03222 =
         0.02914   -0.00641   -0.00367    0.00494
AFIX  43
H27   2    0.448696    1.111037   -0.006684    11.00000   -1.20000
AFIX   0
C28   1    0.411384    0.757856    0.051991    11.00000    0.02258    0.04339 =
         0.02640   -0.00674    0.00134    0.00490
C29   1    0.369583    0.737913    0.007892    11.00000    0.02192    0.02117 =
         0.03503   -0.00018    0.00086   -0.00040
AFIX  43
H29   2    0.375771    0.853838   -0.019548    11.00000   -1.20000
AFIX   0
C210  1    0.319484    0.551634    0.003860    11.00000    0.03173    0.02499 =
         0.02907   -0.00232    0.00337    0.00491
C211  1    0.308860    0.385321    0.045035    11.00000    0.03471    0.02574 =
         0.04105    0.00491   -0.00173   -0.00040
AFIX  43
H211  2    0.274268    0.257645    0.042648    11.00000   -1.20000
AFIX   0
C212  1    0.348892    0.407659    0.089153    11.00000    0.04443    0.03283 =
         0.03695    0.00889    0.00105    0.00535
AFIX  43
H212  2    0.341827    0.294994    0.117041    11.00000   -1.20000
AFIX   0
C213  1    0.398941    0.593039    0.092643    11.00000    0.03466    0.03916 =
         0.03036    0.00580   -0.00635    0.01559
AFIX  43
H213  2    0.425484    0.608840    0.123349    11.00000   -1.20000
AFIX   0
C214  1    0.277074    0.529543   -0.044623    11.00000    0.02612    0.02444 =
         0.04665   -0.00462   -0.00207    0.00089
C215  1    0.226679    0.321619   -0.050659    11.00000    0.04544    0.04326 =
         0.03519   -0.00450   -0.00295   -0.00852
AFIX 137
H21A  2    0.203970    0.334358   -0.084341    11.00000   -1.50000
H21B  2    0.191284    0.331964   -0.023504    11.00000   -1.50000
H21C  2    0.251302    0.160392   -0.048142    11.00000   -1.50000
AFIX   0
C216  1    0.726641    1.623437    0.122136    11.00000    0.04656    0.05993 =
         0.03867   -0.00690   -0.00034   -0.01040
AFIX 137
H21D  2    0.757028    1.627246    0.091809    11.00000   -1.50000
H21E  2    0.754576    1.584669    0.152715    11.00000   -1.50000
H21F  2    0.704237    1.787917    0.126451    11.00000   -1.50000
AFIX   0
H21   2    0.531974    1.005672    0.105247    11.00000   -1.20000
HKLF    4
 
REM  I_200K in Pna2(1)
REM R1 =  0.0996 for   3669 Fo > 4sig(Fo)  and  0.1265 for all   5701 data
REM    372 parameters refined using      5 restraints
 
END  
     
WGHT      0.2000      0.0000 
REM Highest difference peak  0.549,  deepest hole -0.516,  1-sigma level  0.117
Q1    1   0.3009 -0.4182  0.2242  11.00000  0.05    0.55
Q2    1   0.6220  0.9129  0.0988  11.00000  0.05    0.53
Q3    1  -0.0036 -0.8233  0.4047  11.00000  0.05    0.53
Q4    1   0.3186  0.3397 -0.0792  11.00000  0.05    0.48
Q5    1   0.7523  1.7768  0.0744  11.00000  0.05    0.47
Q6    1   0.3181 -0.2715  0.3092  11.00000  0.05    0.47
Q7    1   0.7660  1.9329  0.1138  11.00000  0.05    0.46
Q8    1   0.3713  0.9505 -0.0377  11.00000  0.05    0.43
Q9    1   0.4236  1.2616  0.0056  11.00000  0.05    0.42
Q10   1   0.5535  1.4053  0.0593  11.00000  0.05    0.42
Q11   1   0.6802  1.6052  0.1113  11.00000  0.05    0.42
Q12   1   0.5301  0.9066  0.0388  11.00000  0.05    0.41
Q13   1   0.3322  0.4061  0.0122  11.00000  0.05    0.40
Q14   1  -0.0170 -0.7259  0.3173  11.00000  0.05    0.39
Q15   1   0.1871 -0.8158  0.2711  11.00000  0.05    0.38
Q16   1   0.0815 -0.5488  0.2552  11.00000  0.05    0.38
Q17   1   0.4171  1.0499  0.0009  11.00000  0.05    0.37
Q18   1   0.3278  0.8034 -0.0536  11.00000  0.05    0.37
Q19   1   0.0535 -0.2594  0.4397  11.00000  0.05    0.37
Q20   1   0.1306 -0.3071  0.4195  11.00000  0.05    0.37

#============================================================ 
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
_chemical_properties_physical    Thermochromic
####################################################################### 
# 
# 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_II_298K
_database_code_depnum_ccdc_archive 'CCDC 1401492'
#Added by publCIF



_audit_update_record             
;
2015-05-18 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;


_symmetry_space_group_name_hall  'P 2ac 2ab'
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
1-{3-[(2-Hydroxy-3-methoxy-benzylidene)-amino]-phenyl}-ethanone
_chemical_name_common            
1-{3-[(2-Hydroxy-3-methoxy-benzylidene)-amino]-phenyl}-ethanone
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H15 N O3'
_chemical_formula_sum            'C16 H15 N O3'
_chemical_formula_weight         269.29

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           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

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

_cell_length_a                   4.8773(5)
_cell_length_b                   13.7541(14)
_cell_length_c                   20.3950(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1368.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9476
_exptl_absorpt_correction_T_max  0.9964
_exptl_absorpt_process_details   ?

_exptl_special_details           ?

_diffrn_ambient_temperature      298(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  'Oxford Diffraction Xcalibur Kappa CCD'
_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            5046
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_av_sigmaI/netI    0.1701
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         4.22
_diffrn_reflns_theta_max         26.99
_reflns_number_total             2651
_reflns_number_gt                959
_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)+(0.0295P)²+0.0000P] 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   .
_refine_ls_number_reflns         2651
_refine_ls_number_parameters     187
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1348
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.0830
_refine_ls_wR_factor_gt          0.0710
_refine_ls_goodness_of_fit_ref   0.681
_refine_ls_restrained_S_all      0.681
_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
O1 O 0.5804(5) 0.9641(2) 0.02211(10) 0.0527(7) Uani 1 1 d D . .
H1 H 0.455(5) 0.945(2) 0.0563(10) 0.048(9) Uiso 1 1 d D . .
O2 O 0.9362(4) 1.04607(18) -0.05551(10) 0.0554(7) Uani 1 1 d . . .
O3 O -0.4811(7) 0.6468(2) 0.19215(14) 0.0979(11) Uani 1 1 d . . .
N1 N 0.3342(6) 0.9574(2) 0.13270(12) 0.0477(8) Uani 1 1 d . . .
C1 C 0.6843(7) 1.0726(2) 0.10955(14) 0.0413(9) Uani 1 1 d U . .
C2 C 0.7244(7) 1.0387(3) 0.04729(15) 0.0385(9) Uani 1 1 d . . .
C3 C 0.9207(7) 1.0842(3) 0.00679(14) 0.0438(10) Uani 1 1 d . . .
C4 C 1.0772(7) 1.1586(3) 0.03028(16) 0.0471(10) Uani 1 1 d . . .
H4 H 1.2092 1.1870 0.0035 0.057 Uiso 1 1 calc R . .
C5 C 1.0414(7) 1.1922(3) 0.09364(17) 0.0534(10) Uani 1 1 d . . .
H5 H 1.1475 1.2433 0.1094 0.064 Uiso 1 1 calc R . .
C6 C 0.8461(7) 1.1491(2) 0.13329(17) 0.0500(10) Uani 1 1 d U . .
H6 H 0.8220 1.1710 0.1760 0.060 Uiso 1 1 calc R . .
C7 C 0.4830(7) 1.0280(3) 0.15217(14) 0.0464(10) Uani 1 1 d . . .
H7 H 0.4617 1.0513 0.1947 0.056 Uiso 1 1 calc R . .
C8 C 0.1343(7) 0.9132(3) 0.17428(15) 0.0453(10) Uani 1 1 d . . .
C9 C 0.0656(7) 0.9454(3) 0.23775(14) 0.0550(10) Uani 1 1 d . . .
H9 H 0.1519 0.9997 0.2555 0.066 Uiso 1 1 calc R . .
C10 C -0.1286(7) 0.8965(3) 0.27330(15) 0.0620(13) Uani 1 1 d . . .
H10 H -0.1709 0.9170 0.3156 0.074 Uiso 1 1 calc R . .
C11 C -0.2620(8) 0.8171(3) 0.24692(18) 0.0617(12) Uani 1 1 d . . .
H11 H -0.3941 0.7848 0.2715 0.074 Uiso 1 1 calc R . .
C12 C -0.2011(8) 0.7852(3) 0.18414(18) 0.0490(10) Uani 1 1 d . . .
C13 C -0.0047(7) 0.8345(3) 0.14801(16) 0.0484(10) Uani 1 1 d . . .
H13 H 0.0344 0.8144 0.1055 0.058 Uiso 1 1 calc R . .
C14 C -0.3553(10) 0.7000(3) 0.15594(19) 0.0688(13) Uani 1 1 d . . .
C16 C 1.1597(7) 1.0785(3) -0.09595(15) 0.0665(13) Uani 1 1 d . . .
H16A H 1.1318 1.1453 -0.1077 0.100 Uiso 1 1 calc R . .
H16B H 1.1677 1.0395 -0.1350 0.100 Uiso 1 1 calc R . .
H16C H 1.3286 1.0722 -0.0722 0.100 Uiso 1 1 calc R . .
C15 C -0.3500(9) 0.6862(3) 0.08417(17) 0.0954(16) Uani 1 1 d . . .
H15A H -0.1739 0.6616 0.0712 0.143 Uiso 1 1 calc R . .
H15B H -0.3830 0.7473 0.0628 0.143 Uiso 1 1 calc R . .
H15C H -0.4898 0.6406 0.0718 0.143 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
O1 C2 1.345(4) . ?
O1 H1 0.964(17) . ?
O2 C3 1.377(3) . ?
O2 C16 1.438(3) . ?
O3 C14 1.208(4) . ?
N1 C7 1.275(4) . ?
N1 C8 1.428(4) . ?
C1 C2 1.367(4) . ?
C1 C6 1.402(4) . ?
C1 C7 1.448(4) . ?
C2 C3 1.411(4) . ?
C3 C4 1.364(4) . ?
C4 C5 1.384(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C13 1.386(4) . ?
C8 C9 1.408(4) . ?
C9 C10 1.369(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.380(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.386(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.386(4) . ?
C12 C14 1.506(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.476(4) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
C2 O1 H1 105.3(18) . . ?
C3 O2 C16 116.9(3) . . ?
C7 N1 C8 121.8(3) . . ?
C2 C1 C6 119.8(3) . . ?
C2 C1 C7 120.7(3) . . ?
C6 C1 C7 119.5(3) . . ?
O1 C2 C1 122.7(3) . . ?
O1 C2 C3 118.0(3) . . ?
C1 C2 C3 119.3(3) . . ?
C4 C3 O2 125.4(3) . . ?
C4 C3 C2 120.5(3) . . ?
O2 C3 C2 114.1(3) . . ?
C3 C4 C5 120.5(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 119.3(3) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C1 120.5(3) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
N1 C7 C1 121.4(3) . . ?
N1 C7 H7 119.3 . . ?
C1 C7 H7 119.3 . . ?
C13 C8 C9 119.0(3) . . ?
C13 C8 N1 115.9(3) . . ?
C9 C8 N1 125.1(4) . . ?
C10 C9 C8 119.8(4) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 120.5(3) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C10 C11 C12 120.7(4) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C13 C12 C11 119.0(4) . . ?
C13 C12 C14 121.5(4) . . ?
C11 C12 C14 119.5(4) . . ?
C12 C13 C8 121.0(3) . . ?
C12 C13 H13 119.5 . . ?
C8 C13 H13 119.5 . . ?
O3 C14 C15 122.5(4) . . ?
O3 C14 C12 119.5(4) . . ?
C15 C14 C12 118.0(4) . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C6 C1 C2 O1 178.5(3) . . . . ?
C7 C1 C2 O1 0.7(5) . . . . ?
C6 C1 C2 C3 -2.7(4) . . . . ?
C7 C1 C2 C3 179.5(3) . . . . ?
C16 O2 C3 C4 8.8(5) . . . . ?
C16 O2 C3 C2 -170.6(3) . . . . ?
O1 C2 C3 C4 -178.4(3) . . . . ?
C1 C2 C3 C4 2.7(5) . . . . ?
O1 C2 C3 O2 1.0(4) . . . . ?
C1 C2 C3 O2 -177.8(3) . . . . ?
O2 C3 C4 C5 179.0(3) . . . . ?
C2 C3 C4 C5 -1.6(5) . . . . ?
C3 C4 C5 C6 0.5(5) . . . . ?
C4 C5 C6 C1 -0.5(5) . . . . ?
C2 C1 C6 C5 1.6(5) . . . . ?
C7 C1 C6 C5 179.4(3) . . . . ?
C8 N1 C7 C1 -179.7(3) . . . . ?
C2 C1 C7 N1 -1.3(5) . . . . ?
C6 C1 C7 N1 -179.1(3) . . . . ?
C7 N1 C8 C13 -177.2(3) . . . . ?
C7 N1 C8 C9 4.7(5) . . . . ?
C13 C8 C9 C10 2.5(5) . . . . ?
N1 C8 C9 C10 -179.5(3) . . . . ?
C8 C9 C10 C11 -1.4(5) . . . . ?
C9 C10 C11 C12 0.3(6) . . . . ?
C10 C11 C12 C13 -0.3(5) . . . . ?
C10 C11 C12 C14 -178.4(3) . . . . ?
C11 C12 C13 C8 1.4(5) . . . . ?
C14 C12 C13 C8 179.5(3) . . . . ?
C9 C8 C13 C12 -2.5(5) . . . . ?
N1 C8 C13 C12 179.3(3) . . . . ?
C13 C12 C14 O3 164.7(4) . . . . ?
C11 C12 C14 O3 -17.2(6) . . . . ?
C13 C12 C14 C15 -16.4(5) . . . . ?
C11 C12 C14 C15 161.7(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        26.99
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.030

#============================================================
_iucr_refine_instruction_details 
;

TITL II_298K in P212121
CELL  0.71073   4.8773  13.7541  20.3950   90.000   90.000   90.000
ZERR     4.00   0.0005   0.0014   0.0018    0.000    0.000    0.000
LATT  -1
SYMM  1/2 - X, - Y, 1/2 + Z
SYMM  1/2 + X, 1/2 - Y, - Z
SYMM  - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    N    O
UNIT  64   60   4    12
MERG   2
OMIT    -4.00  54.00
delu  0.001 0.001 C1  C6
DFIX  0.95  O1 H1
FMAP   2
PLAN   20
SIZE     0.04   0.06   0.60
ACTA
BOND
BOND   $H
CONF
LIST   4
L.S.   4
TEMP    25.00
WGHT    0.029500
FVAR       6.35502
O1    4    0.580388    0.964146    0.022109    11.00000    0.05766    0.05030 =
         0.05014   -0.00222    0.01125   -0.01409
H1    2    0.455103    0.944917    0.056294    11.00000    0.04792
O2    4    0.936211    1.046072   -0.055513    11.00000    0.05372    0.05705 =
         0.05546   -0.00270    0.01263   -0.01174
O3    4   -0.481140    0.646752    0.192149    11.00000    0.12357    0.06917 =
         0.10102    0.02111    0.02278   -0.03553
N1    3    0.334213    0.957396    0.132703    11.00000    0.04152    0.05051 =
         0.05100    0.00818    0.00379   -0.00103
C1    1    0.684333    1.072583    0.109550    11.00000    0.03441    0.03856 =
         0.05080    0.00302   -0.00118    0.00788
C2    1    0.724413    1.038703    0.047291    11.00000    0.03644    0.03476 =
         0.04433    0.00021    0.00178    0.00111
C3    1    0.920708    1.084216    0.006793    11.00000    0.04409    0.04212 =
         0.04519    0.00108    0.00271    0.00503
C4    1    1.077244    1.158610    0.030278    11.00000    0.04303    0.03993 =
         0.05835    0.00454    0.00339   -0.00274
AFIX  43
H4    2    1.209191    1.186981    0.003490    11.00000   -1.20000
AFIX   0
C5    1    1.041366    1.192229    0.093637    11.00000    0.05001    0.03871 =
         0.07138   -0.00570   -0.00510   -0.00721
AFIX  43
H5    2    1.147466    1.243315    0.109404    11.00000   -1.20000
AFIX   0
C6    1    0.846108    1.149091    0.133288    11.00000    0.05003    0.03796 =
         0.06206   -0.00599    0.00044    0.00732
AFIX  43
H6    2    0.821974    1.171023    0.176034    11.00000   -1.20000
AFIX   0
C7    1    0.483017    1.027974    0.152168    11.00000    0.04211    0.05369 =
         0.04332   -0.00219   -0.00562    0.01449
AFIX  43
H7    2    0.461739    1.051293    0.194667    11.00000   -1.20000
AFIX   0
C8    1    0.134323    0.913240    0.174281    11.00000    0.04058    0.04641 =
         0.04880    0.01430    0.00372    0.00469
C9    1    0.065639    0.945387    0.237745    11.00000    0.05290    0.06573 =
         0.04647    0.00620   -0.00289   -0.00495
AFIX  43
H9    2    0.151931    0.999660    0.255461    11.00000   -1.20000
AFIX   0
C10   1   -0.128588    0.896499    0.273300    11.00000    0.05765    0.08796 =
         0.04050    0.00486    0.00654   -0.01358
AFIX  43
H10   2   -0.170927    0.916952    0.315568    11.00000   -1.20000
AFIX   0
C11   1   -0.262006    0.817132    0.246925    11.00000    0.05232    0.07805 =
         0.05471    0.02702   -0.00241    0.00165
AFIX  43
H11   2   -0.394091    0.784764    0.271523    11.00000   -1.20000
AFIX   0
C12   1   -0.201111    0.785175    0.184136    11.00000    0.04900    0.04078 =
         0.05715    0.01496    0.00147    0.00303
C13   1   -0.004729    0.834452    0.148006    11.00000    0.05176    0.03976 =
         0.05369    0.00700    0.01074    0.00357
AFIX  43
H13   2    0.034386    0.814362    0.105482    11.00000   -1.20000
AFIX   0
C14   1   -0.355302    0.700015    0.155942    11.00000    0.08763    0.04885 =
         0.07004    0.00826    0.00575    0.00941
C16   1    1.159652    1.078479   -0.095952    11.00000    0.06127    0.07625 =
         0.06203    0.01189    0.01218   -0.01264
AFIX 137
H16A  2    1.131849    1.145337   -0.107718    11.00000   -1.50000
H16B  2    1.167694    1.039517   -0.134959    11.00000   -1.50000
H16C  2    1.328629    1.072223   -0.072184    11.00000   -1.50000
AFIX   0
C15   1   -0.350036    0.686176    0.084172    11.00000    0.12454    0.06589 =
         0.09568   -0.01247    0.01723   -0.02365
AFIX 137
H15A  2   -0.173888    0.661637    0.071239    11.00000   -1.50000
H15B  2   -0.383015    0.747293    0.062850    11.00000   -1.50000
H15C  2   -0.489781    0.640601    0.071758    11.00000   -1.50000
HKLF    4
 
REM  o3a_IN in P212121
REM R1 =  0.0382 for    959 Fo > 4sig(Fo)  and  0.1348 for all   2651 data
REM    187 parameters refined using      2 restraints
 
END  
     
WGHT      0.0295      0.0000 
REM Highest difference peak  0.125,  deepest hole -0.128,  1-sigma level  0.030
Q1    1   0.0401  0.9720  0.0759  11.00000  0.05    0.13
Q2    1   0.9177  1.0797 -0.0251  11.00000  0.05    0.11
Q3    1   0.1949  1.0831  0.1763  11.00000  0.05    0.11
Q4    1   1.0279  1.1629  0.2546  11.00000  0.05    0.10
Q5    1   0.1935  0.9588  0.1417  11.00000  0.05    0.10
Q6    1   0.4564  1.0566  0.1695  11.00000  0.05    0.10
Q7    1   1.1647  1.2159 -0.0656  11.00000  0.05    0.09
Q8    1   1.1884  0.9317 -0.1220  11.00000  0.05    0.09
Q9    1   0.1996  1.0347  0.1115  11.00000  0.05    0.09
Q10   1   1.2748  1.2187 -0.0240  11.00000  0.05    0.09
Q11   1   0.6020  1.1174  0.2375  11.00000  0.05    0.09
Q12   1   1.0305  1.0089 -0.0462  11.00000  0.05    0.09
Q13   1   1.1719  1.0561  0.0537  11.00000  0.05    0.09
Q14   1   0.0802  0.9261  0.0462  11.00000  0.05    0.08
Q15   1   0.9614  1.2381 -0.0811  11.00000  0.05    0.08
Q16   1   0.8246  0.9564  0.0905  11.00000  0.05    0.08
Q17   1   0.3281  1.0410  0.0884  11.00000  0.05    0.08
Q18   1   0.9865  1.0508 -0.1968  11.00000  0.05    0.08
Q19   1   0.0801  0.7750  0.0975  11.00000  0.05    0.08
Q20   1  -0.4832  0.8353  0.0845  11.00000  0.05    0.08


#============================================================ 
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
_chemical_properties_physical    'Heat-sensitive, Thermochromic'
####################################################################### 
# 
# 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_III_298K
_database_code_depnum_ccdc_archive 'CCDC 1401493'
#Added by publCIF



_audit_update_record             
;
2015-05-18 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;


_symmetry_space_group_name_hall  'P 2ac 2ab'
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
1-{3-[(2-Hydroxy-3-methoxy-benzylidene)-amino]-phenyl}-ethanone
_chemical_name_common            
1-{3-[(2-Hydroxy-3-methoxy-benzylidene)-amino]-phenyl}-ethanone
_chemical_melting_point          391
_chemical_formula_moiety         'C16 H15 N O3'
_chemical_formula_sum            'C16 H15 N O3'
_chemical_formula_weight         269.29

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           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

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

_cell_length_a                   7.4681(3)
_cell_length_b                   13.1048(5)
_cell_length_c                   13.9995(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1370.10(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    298
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.44
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9510
_exptl_absorpt_correction_T_max  0.9612
_exptl_absorpt_process_details   ?

_exptl_special_details           ?

_diffrn_ambient_temperature      298
_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  'Oxford Diffraction Xcalibur Kappa CCD'
_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            10075
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0336
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.26
_diffrn_reflns_theta_max         27.00
_reflns_number_total             2966
_reflns_number_gt                2012
_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)+(0.1594P)²+0.0000P] 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   .
_refine_ls_number_reflns         2966
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0705
_refine_ls_wR_factor_ref         0.2302
_refine_ls_wR_factor_gt          0.2196
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
O1 O 0.5357(4) 0.2948(2) 0.41105(17) 0.0717(8) Uani 1 1 d . . .
H1 H 0.647(7) 0.258(4) 0.402(3) 0.083(13) Uiso 1 1 d . . .
O2 O 0.2260(4) 0.3803(2) 0.44200(18) 0.0730(8) Uani 1 1 d . . .
O3 O 1.2187(5) 0.1872(3) 0.0132(2) 0.1035(12) Uani 1 1 d . . .
N1 N 0.7862(4) 0.2402(2) 0.29057(18) 0.0526(7) Uani 1 1 d . . .
C1 C 0.5268(4) 0.3334(2) 0.2436(2) 0.0482(7) Uani 1 1 d . . .
C2 C 0.4514(5) 0.3350(2) 0.3340(2) 0.0501(8) Uani 1 1 d . . .
C3 C 0.2865(5) 0.3828(2) 0.3498(2) 0.0518(8) Uani 1 1 d . . .
C4 C 0.2004(5) 0.4296(3) 0.2740(3) 0.0607(9) Uani 1 1 d . . .
H4 H 0.0912 0.4621 0.2836 0.073 Uiso 1 1 calc R . .
C5 C 0.2773(6) 0.4278(3) 0.1832(2) 0.0612(9) Uani 1 1 d . . .
H5 H 0.2176 0.4591 0.1328 0.073 Uiso 1 1 calc R . .
C6 C 0.4346(5) 0.3824(3) 0.1667(2) 0.0566(9) Uani 1 1 d . . .
H6 H 0.4838 0.3826 0.1056 0.068 Uiso 1 1 calc R . .
C7 C 0.6965(4) 0.2848(2) 0.2248(2) 0.0472(7) Uani 1 1 d . . .
H7 H 0.7420 0.2859 0.1630 0.057 Uiso 1 1 calc R . .
C8 C 0.9528(5) 0.1910(2) 0.2727(2) 0.0499(8) Uani 1 1 d . . .
C13 C 1.0327(5) 0.1432(3) 0.3501(2) 0.0568(8) Uani 1 1 d . . .
H13 H 0.9788 0.1459 0.4100 0.068 Uiso 1 1 calc R . .
C12 C 1.1922(5) 0.0918(3) 0.3381(3) 0.0721(11) Uani 1 1 d . . .
H12 H 1.2423 0.0567 0.3893 0.086 Uiso 1 1 calc R . .
C11 C 1.2770(5) 0.0918(3) 0.2520(3) 0.0592(9) Uani 1 1 d . . .
H11 H 1.3867 0.0589 0.2457 0.071 Uiso 1 1 calc R . .
C10 C 1.2017(4) 0.1404(2) 0.1733(2) 0.0499(8) Uani 1 1 d . . .
C9 C 1.0369(5) 0.1888(2) 0.1851(2) 0.0502(7) Uani 1 1 d . . .
H9 H 0.9827 0.2201 0.1329 0.060 Uiso 1 1 calc R . .
C14 C 1.2898(5) 0.1431(3) 0.0789(2) 0.0563(8) Uani 1 1 d . . .
C15 C 1.4665(6) 0.0954(4) 0.0634(4) 0.0851(13) Uani 1 1 d . . .
H15A H 1.5202 0.1234 0.0068 0.128 Uiso 1 1 calc R . .
H15B H 1.4520 0.0231 0.0558 0.128 Uiso 1 1 calc R . .
H15C H 1.5423 0.1088 0.1174 0.128 Uiso 1 1 calc R . .
C16 C 0.0534(6) 0.4236(4) 0.4588(3) 0.0760(12) Uani 1 1 d . . .
H16A H 0.0606 0.4965 0.4535 0.114 Uiso 1 1 calc R . .
H16B H 0.0136 0.4056 0.5218 0.114 Uiso 1 1 calc R . .
H16C H -0.0298 0.3979 0.4125 0.114 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
O1 C2 1.355(4) . ?
O1 H1 0.96(5) . ?
O2 C3 1.367(4) . ?
O2 C16 1.428(5) . ?
O3 C14 1.209(4) . ?
N1 C7 1.280(4) . ?
N1 C8 1.424(5) . ?
C1 C2 1.385(5) . ?
C1 C6 1.430(5) . ?
C1 C7 1.443(5) . ?
C2 C3 1.400(5) . ?
C3 C4 1.384(5) . ?
C4 C5 1.396(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.337(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.378(4) . ?
C8 C13 1.387(5) . ?
C13 C12 1.379(6) . ?
C13 H13 0.9300 . ?
C12 C11 1.362(6) . ?
C12 H12 0.9300 . ?
C11 C10 1.391(5) . ?
C11 H11 0.9300 . ?
C10 C9 1.395(5) . ?
C10 C14 1.476(5) . ?
C9 H9 0.9300 . ?
C14 C15 1.477(6) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C2 O1 H1 119(3) . . ?
C3 O2 C16 116.4(3) . . ?
C7 N1 C8 122.5(3) . . ?
C2 C1 C6 119.1(3) . . ?
C2 C1 C7 122.0(3) . . ?
C6 C1 C7 118.9(3) . . ?
O1 C2 C1 122.2(3) . . ?
O1 C2 C3 117.2(3) . . ?
C1 C2 C3 120.6(3) . . ?
O2 C3 C4 125.5(3) . . ?
O2 C3 C2 115.4(3) . . ?
C4 C3 C2 119.1(3) . . ?
C3 C4 C5 120.0(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 121.7(3) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C1 119.5(3) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
N1 C7 C1 122.0(3) . . ?
N1 C7 H7 119.0 . . ?
C1 C7 H7 119.0 . . ?
C9 C8 C13 119.4(3) . . ?
C9 C8 N1 124.4(3) . . ?
C13 C8 N1 116.3(3) . . ?
C12 C13 C8 119.8(3) . . ?
C12 C13 H13 120.1 . . ?
C8 C13 H13 120.1 . . ?
C11 C12 C13 120.7(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C11 C10 120.9(3) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C10 C9 118.1(3) . . ?
C11 C10 C14 122.7(3) . . ?
C9 C10 C14 119.2(3) . . ?
C8 C9 C10 121.2(3) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
O3 C14 C10 119.8(3) . . ?
O3 C14 C15 118.8(3) . . ?
C10 C14 C15 121.4(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
C6 C1 C2 O1 -176.5(3) . . . . ?
C7 C1 C2 O1 2.8(5) . . . . ?
C6 C1 C2 C3 0.7(5) . . . . ?
C7 C1 C2 C3 -180.0(3) . . . . ?
C16 O2 C3 C4 4.6(5) . . . . ?
C16 O2 C3 C2 -176.6(3) . . . . ?
O1 C2 C3 O2 -2.2(4) . . . . ?
C1 C2 C3 O2 -179.5(3) . . . . ?
O1 C2 C3 C4 176.6(3) . . . . ?
C1 C2 C3 C4 -0.7(5) . . . . ?
O2 C3 C4 C5 179.2(3) . . . . ?
C2 C3 C4 C5 0.6(5) . . . . ?
C3 C4 C5 C6 -0.5(6) . . . . ?
C4 C5 C6 C1 0.5(5) . . . . ?
C2 C1 C6 C5 -0.6(5) . . . . ?
C7 C1 C6 C5 -179.9(3) . . . . ?
C8 N1 C7 C1 179.3(3) . . . . ?
C2 C1 C7 N1 0.2(5) . . . . ?
C6 C1 C7 N1 179.6(3) . . . . ?
C7 N1 C8 C9 2.1(5) . . . . ?
C7 N1 C8 C13 -178.2(3) . . . . ?
C9 C8 C13 C12 -1.8(5) . . . . ?
N1 C8 C13 C12 178.5(3) . . . . ?
C8 C13 C12 C11 3.4(6) . . . . ?
C13 C12 C11 C10 -2.4(6) . . . . ?
C12 C11 C10 C9 -0.2(5) . . . . ?
C12 C11 C10 C14 179.4(4) . . . . ?
C13 C8 C9 C10 -0.8(5) . . . . ?
N1 C8 C9 C10 178.9(3) . . . . ?
C11 C10 C9 C8 1.8(5) . . . . ?
C14 C10 C9 C8 -177.8(3) . . . . ?
C11 C10 C14 O3 -179.5(4) . . . . ?
C9 C10 C14 O3 0.2(5) . . . . ?
C11 C10 C14 C15 -1.2(6) . . . . ?
C9 C10 C14 C15 178.4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.608
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.062

#============================================================
_iucr_refine_instruction_details 
;

TITL III_298K in P2(1)2(1)2(1)
CELL  0.71073   7.4681  13.1048  13.9995   90.000   90.000   90.000
ZERR     4.00   0.0003   0.0005   0.0005    0.000    0.000    0.000
LATT  -1
SYMM  1/2 - X, - Y, 1/2 + Z
SYMM  1/2 + X, 1/2 - Y, - Z
SYMM  - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    N    O
UNIT  64   60   4    12
MERG   2
OMIT    -4.00  54.00
FMAP   2
PLAN   20
SIZE     0.44   0.48   0.56
ACTA
BOND
BOND   $H
CONF
LIST   4
L.S.   4
TEMP    25.00
WGHT    0.159400
FVAR       8.65788
O1    4    0.535683    0.294776    0.411048    11.00000    0.07734    0.09194 =
         0.04597    0.00777    0.00401    0.02604
H1    2    0.646529    0.258466    0.402071    11.00000    0.08350
O2    4    0.225957    0.380278    0.441995    11.00000    0.07345    0.08706 =
         0.05854    0.00096    0.01693    0.01685
O3    4    1.218675    0.187166    0.013203    11.00000    0.09065    0.16905 =
         0.05072    0.01166    0.00527    0.03738
N1    3    0.786178    0.240204    0.290574    11.00000    0.06121    0.05563 =
         0.04085    0.00269    0.00103    0.00507
C1    1    0.526783    0.333416    0.243598    11.00000    0.05676    0.04751 =
         0.04021    0.00442   -0.00590   -0.00351
C2    1    0.451445    0.334973    0.333996    11.00000    0.05707    0.05002 =
         0.04325    0.00602   -0.00723    0.00356
C3    1    0.286467    0.382815    0.349840    11.00000    0.05926    0.05131 =
         0.04479   -0.00196    0.00339   -0.00180
C4    1    0.200380    0.429555    0.274037    11.00000    0.05282    0.05118 =
         0.07810   -0.00291   -0.00788    0.00425
AFIX  43
H4    2    0.091221    0.462136    0.283628    11.00000   -1.20000
AFIX   0
C5    1    0.277328    0.427825    0.183152    11.00000    0.06949    0.06028 =
         0.05385    0.01053   -0.01112    0.00669
AFIX  43
H5    2    0.217598    0.459112    0.132753    11.00000   -1.20000
AFIX   0
C6    1    0.434640    0.382370    0.166659    11.00000    0.07249    0.05750 =
         0.03969    0.01001   -0.00592   -0.00139
AFIX  43
H6    2    0.483753    0.382591    0.105613    11.00000   -1.20000
AFIX   0
C7    1    0.696459    0.284796    0.224763    11.00000    0.05489    0.05052 =
         0.03617    0.00561    0.00081    0.00082
AFIX  43
H7    2    0.742049    0.285876    0.162952    11.00000   -1.20000
AFIX   0
C8    1    0.952819    0.191004    0.272663    11.00000    0.05344    0.05021 =
         0.04618   -0.00019   -0.00582   -0.00420
C13   1    1.032653    0.143230    0.350142    11.00000    0.06668    0.06198 =
         0.04165    0.00564   -0.00916   -0.01040
AFIX  43
H13   2    0.978810    0.145879    0.409991    11.00000   -1.20000
AFIX   0
C12   1    1.192175    0.091785    0.338101    11.00000    0.06669    0.08532 =
         0.06417    0.02518   -0.02391   -0.00902
AFIX  43
H12   2    1.242308    0.056724    0.389294    11.00000   -1.20000
AFIX   0
C11   1    1.277020    0.091821    0.251974    11.00000    0.04795    0.06601 =
         0.06371    0.00980   -0.00949    0.00123
AFIX  43
H11   2    1.386722    0.058914    0.245689    11.00000   -1.20000
AFIX   0
C10   1    1.201748    0.140433    0.173284    11.00000    0.04771    0.05181 =
         0.05025    0.00504   -0.00515   -0.00295
C9    1    1.036873    0.188776    0.185083    11.00000    0.06057    0.05190 =
         0.03813    0.00251   -0.00646    0.00082
AFIX  43
H9    2    0.982713    0.220058    0.132922    11.00000   -1.20000
AFIX   0
C14   1    1.289793    0.143126    0.078944    11.00000    0.05780    0.06063 =
         0.05032    0.00531    0.00209    0.00843
C15   1    1.466538    0.095444    0.063372    11.00000    0.07937    0.08853 =
         0.08740    0.00702    0.03112    0.02467
AFIX 137
H15A  2    1.520233    0.123445    0.006849    11.00000   -1.50000
H15B  2    1.452033    0.023109    0.055782    11.00000   -1.50000
H15C  2    1.542261    0.108777    0.117362    11.00000   -1.50000
AFIX   0
C16   1    0.053445    0.423617    0.458820    11.00000    0.06744    0.09411 =
         0.06632   -0.00636    0.01354    0.01496
AFIX 137
H16A  2    0.060564    0.496541    0.453526    11.00000   -1.50000
H16B  2    0.013585    0.405568    0.521787    11.00000   -1.50000
H16C  2   -0.029825    0.397886    0.412463    11.00000   -1.50000
HKLF    4
 
REM  O3A_APS_P212121 in P2(1)2(1)2(1)
REM R1 =  0.0705 for   2012 Fo > 4sig(Fo)  and  0.0921 for all   2966 data
REM    187 parameters refined using      0 restraints
 
END  
     
WGHT      0.1594      0.0000 
REM Highest difference peak  0.608,  deepest hole -0.205,  1-sigma level  0.062
Q1    1   0.9626  0.2196  0.0932  11.00000  0.05    0.61
Q2    1   0.2747  0.3145  0.4869  11.00000  0.05    0.58
Q3    1   1.2481  0.1188  0.0490  11.00000  0.05    0.22
Q4    1   1.2523  0.1118  0.1204  11.00000  0.05    0.22
Q5    1   0.5218  0.3149  0.2268  11.00000  0.05    0.22
Q6    1   0.4578  0.2835  0.4979  11.00000  0.05    0.20
Q7    1   1.4274  0.0776 -0.0133  11.00000  0.05    0.20
Q8    1   0.4619  0.3102  0.3007  11.00000  0.05    0.19
Q9    1   1.2689  0.3164  0.0611  11.00000  0.05    0.18
Q10   1   1.4665  0.1192 -0.0891  11.00000  0.05    0.17
Q11   1   1.4967  0.1349 -0.0962  11.00000  0.05    0.17
Q12   1  -0.0296  0.4072  0.4354  11.00000  0.05    0.17
Q13   1   0.2141  0.3552  0.4298  11.00000  0.05    0.17
Q14   1   0.7740  0.1451  0.2603  11.00000  0.05    0.16
Q15   1   0.7781  0.2170  0.2847  11.00000  0.05    0.16
Q16   1   1.0385  0.1235  0.3368  11.00000  0.05    0.15
Q17   1  -0.1386  0.3224  0.4750  11.00000  0.05    0.15
Q18   1   1.0604  0.3403  0.1125  11.00000  0.05    0.15
Q19   1   1.4883  0.1157  0.2067  11.00000  0.05    0.15
Q20   1   0.2856  0.2708  0.3157  11.00000  0.05    0.15

;

#============================================================

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Absolute Ethanol'
_chemical_properties_physical    Thermochromic
