# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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_2c
_database_code_depnum_ccdc_archive 'CCDC 1504720'
_audit_update_record             
;
2016-09-16 deposited with the CCDC.
2016-10-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        
'(E)--4--(4--Nitrophenylmethylenimino)--2,6--dimethylphenol '
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H14 N2 O3, H2 O'
_chemical_formula_sum            'C15 H16 N2 O4'
_chemical_formula_weight         288.30

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.7540(2)
_cell_length_b                   13.5346(3)
_cell_length_c                   11.9125(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.9410(10)
_cell_angle_gamma                90
_cell_volume                     1401.07(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4956
_cell_measurement_theta_min      0.24
_cell_measurement_theta_max      0.24

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9648
_exptl_absorpt_correction_T_max  0.9763
_exptl_absorpt_process_details   
;
Bruker APEX2, SAINT and SADABS, version 2011.8-0; Bruker AXS Inc., 
Madison, Wisconsin, USA
;





_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10748
_diffrn_reflns_av_unetI/netI     0.0145
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.287
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2755
_reflns_number_gt                2303
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0622P)²+0.4165P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2755
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1191
_refine_ls_wR_factor_gt          0.1108
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.45741(15) 0.63491(10) 0.33390(10) 0.0262(3) Uani 1 1 d . . . . .
C2 C 0.56652(15) 0.62381(10) 0.25847(11) 0.0296(3) Uani 1 1 d . . . . .
H2 H 0.5977 0.5595 0.2389 0.036 Uiso 1 1 calc R U . . .
C3 C 0.62923(16) 0.70541(10) 0.21231(12) 0.0309(3) Uani 1 1 d . . . . .
H3 H 0.7032 0.6982 0.1607 0.037 Uiso 1 1 calc R U . . .
C4 C 0.58192(15) 0.79832(10) 0.24293(11) 0.0281(3) Uani 1 1 d . . . . .
C5 C 0.47489(15) 0.81199(10) 0.31725(12) 0.0302(3) Uani 1 1 d . . . . .
H5 H 0.4439 0.8765 0.3361 0.036 Uiso 1 1 calc R U . . .
C6 C 0.41364(15) 0.72950(10) 0.36373(11) 0.0299(3) Uani 1 1 d . . . . .
H6 H 0.3412 0.7373 0.4164 0.036 Uiso 1 1 calc R U . . .
C7 C 0.39006(15) 0.54861(10) 0.38440(11) 0.0277(3) Uani 1 1 d . . . . .
H7 H 0.3449 0.5564 0.4525 0.033 Uiso 1 1 calc R U . . .
C9 C 0.32787(15) 0.38029(9) 0.38919(10) 0.0247(3) Uani 1 1 d . . . . .
C10 C 0.21386(15) 0.38429(9) 0.46116(10) 0.0260(3) Uani 1 1 d . . . . .
H10 H 0.1751 0.4466 0.4812 0.031 Uiso 1 1 calc R U . . .
C11 C 0.15609(14) 0.29845(10) 0.50400(10) 0.0260(3) Uani 1 1 d . . . . .
C12 C 0.21545(15) 0.20720(9) 0.47427(10) 0.0251(3) Uani 1 1 d . . . . .
C13 C 0.33302(15) 0.20143(9) 0.40505(10) 0.0261(3) Uani 1 1 d . . . . .
C14 C 0.38521(15) 0.28886(10) 0.36213(10) 0.0269(3) Uani 1 1 d . . . . .
H14 H 0.4625 0.2860 0.3127 0.032 Uiso 1 1 calc R U . . .
C15 C 0.03259(17) 0.30298(11) 0.58110(13) 0.0366(3) Uani 1 1 d . . . . .
H15A H 0.0083 0.3722 0.5954 0.055 Uiso 1 1 calc R U . . .
H15B H 0.0688 0.2703 0.6528 0.055 Uiso 1 1 calc R U . . .
H15C H -0.0599 0.2694 0.5453 0.055 Uiso 1 1 calc R U . . .
C16 C 0.40232(18) 0.10392(11) 0.37814(13) 0.0369(3) Uani 1 1 d . . . . .
H16A H 0.3303 0.0680 0.3233 0.055 Uiso 1 1 calc R U . . .
H16B H 0.4231 0.0648 0.4475 0.055 Uiso 1 1 calc R U . . .
H16C H 0.4987 0.1154 0.3460 0.055 Uiso 1 1 calc R U . . .
N1 N 0.64852(14) 0.88560(9) 0.19435(11) 0.0383(3) Uani 1 1 d . . . . .
N8 N 0.39104(12) 0.46359(8) 0.33869(9) 0.0278(3) Uani 1 1 d . . . . .
O1 O 0.74621(16) 0.87270(9) 0.13065(12) 0.0602(4) Uani 1 1 d . . . . .
O2 O 0.60364(16) 0.96700(8) 0.21863(13) 0.0604(4) Uani 1 1 d . . . . .
O3 O 0.16112(12) 0.12094(7) 0.51532(8) 0.0346(3) Uani 1 1 d . . . . .
H3O H 0.0645 0.1269 0.5473 0.041 Uiso 1 1 d R U . . .
O1W O 0.88690(15) 0.06929(9) 0.59468(10) 0.0555(4) Uani 1 1 d . . . . .
H1WA H 0.8970 0.0609 0.6733 0.083 Uiso 1 1 d R U . . .
H1WB H 0.8698 0.0171 0.5682 0.083 Uiso 1 1 d R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.3946(19) . ?
C1 C2 1.3962(19) . ?
C1 C7 1.4696(18) . ?
C2 C3 1.3772(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.3865(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.377(2) . ?
C4 N1 1.4669(17) . ?
C5 C6 1.3829(19) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N8 1.2735(17) . ?
C7 H7 0.9500 . ?
C9 C14 1.3879(18) . ?
C9 C10 1.3931(18) . ?
C9 N8 1.4210(16) . ?
C10 C11 1.3886(18) . ?
C10 H10 0.9500 . ?
C11 C12 1.4019(18) . ?
C11 C15 1.5020(18) . ?
C12 O3 1.3728(15) . ?
C12 C13 1.3966(18) . ?
C13 C14 1.3881(18) . ?
C13 C16 1.5032(18) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
N1 O2 1.2163(17) . ?
N1 O1 1.2225(18) . ?
O3 H3O 0.9721 . ?
O1W H1WA 0.9370 . ?
O1W H1WB 0.7804 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 119.55(12) . . ?
C6 C1 C7 119.28(12) . . ?
C2 C1 C7 121.15(12) . . ?
C3 C2 C1 120.48(12) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 118.44(12) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C5 C4 C3 122.62(12) . . ?
C5 C4 N1 118.63(12) . . ?
C3 C4 N1 118.75(12) . . ?
C4 C5 C6 118.41(12) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C5 C6 C1 120.48(12) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
N8 C7 C1 121.29(12) . . ?
N8 C7 H7 119.4 . . ?
C1 C7 H7 119.4 . . ?
C14 C9 C10 118.92(11) . . ?
C14 C9 N8 116.03(11) . . ?
C10 C9 N8 125.04(11) . . ?
C11 C10 C9 120.90(12) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 118.79(11) . . ?
C10 C11 C15 120.77(12) . . ?
C12 C11 C15 120.44(12) . . ?
O3 C12 C13 118.33(11) . . ?
O3 C12 C11 120.28(11) . . ?
C13 C12 C11 121.37(11) . . ?
C14 C13 C12 117.94(11) . . ?
C14 C13 C16 120.71(12) . . ?
C12 C13 C16 121.35(11) . . ?
C9 C14 C13 122.02(12) . . ?
C9 C14 H14 119.0 . . ?
C13 C14 H14 119.0 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O2 N1 O1 123.18(13) . . ?
O2 N1 C4 118.71(13) . . ?
O1 N1 C4 118.11(12) . . ?
C7 N8 C9 120.85(11) . . ?
C12 O3 H3O 115.1 . . ?
H1WA O1W H1WB 106.5 . . ?

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 C3 -0.9(2) . . . . ?
C7 C1 C2 C3 -179.64(12) . . . . ?
C1 C2 C3 C4 0.3(2) . . . . ?
C2 C3 C4 C5 -0.1(2) . . . . ?
C2 C3 C4 N1 179.83(12) . . . . ?
C3 C4 C5 C6 0.6(2) . . . . ?
N1 C4 C5 C6 -179.33(11) . . . . ?
C4 C5 C6 C1 -1.28(19) . . . . ?
C2 C1 C6 C5 1.5(2) . . . . ?
C7 C1 C6 C5 -179.82(12) . . . . ?
C6 C1 C7 N8 160.05(13) . . . . ?
C2 C1 C7 N8 -21.24(19) . . . . ?
C14 C9 C10 C11 -1.06(19) . . . . ?
N8 C9 C10 C11 178.16(11) . . . . ?
C9 C10 C11 C12 0.50(18) . . . . ?
C9 C10 C11 C15 -179.68(12) . . . . ?
C10 C11 C12 O3 179.87(11) . . . . ?
C15 C11 C12 O3 0.06(19) . . . . ?
C10 C11 C12 C13 1.47(19) . . . . ?
C15 C11 C12 C13 -178.35(12) . . . . ?
O3 C12 C13 C14 178.77(11) . . . . ?
C11 C12 C13 C14 -2.79(19) . . . . ?
O3 C12 C13 C16 -1.67(18) . . . . ?
C11 C12 C13 C16 176.76(12) . . . . ?
C10 C9 C14 C13 -0.35(19) . . . . ?
N8 C9 C14 C13 -179.63(11) . . . . ?
C12 C13 C14 C9 2.24(19) . . . . ?
C16 C13 C14 C9 -177.33(12) . . . . ?
C5 C4 N1 O2 -2.2(2) . . . . ?
C3 C4 N1 O2 177.85(13) . . . . ?
C5 C4 N1 O1 178.23(13) . . . . ?
C3 C4 N1 O1 -1.7(2) . . . . ?
C1 C7 N8 C9 178.95(11) . . . . ?
C14 C9 N8 C7 -155.36(12) . . . . ?
C10 C9 N8 C7 25.40(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3O O1W 0.97 1.89 2.7737(16) 150.5 1_455
O1W H1WA N8 0.94 2.00 2.9365(15) 172.7 4_666
O1W H1WB O3 0.78 2.12 2.8966(16) 174.3 3_656

_refine_diff_density_max         0.232
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.044

_shelxl_version_number           2014/6


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
####################################################################### 
# 
# 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_2d
_database_code_depnum_ccdc_archive 'CCDC 1504721'
_audit_update_record             
;
2016-09-16 deposited with the CCDC.
2016-10-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        
(E)--4--(4--Nitrophenylmethylenimino)--2,6--dibromophenol
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H8 Br2 N2 O3'
_chemical_formula_sum            'C13 H8 Br2 N2 O3'
_chemical_formula_weight         400.03

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5277(3)
_cell_length_b                   10.5750(4)
_cell_length_c                   15.1816(5)
_cell_angle_alpha                93.2580(10)
_cell_angle_beta                 101.7060(10)
_cell_angle_gamma                92.7190(10)
_cell_volume                     1336.00(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9461
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      27.59

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.989
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    6.075
_shelx_estimated_absorpt_T_min   0.195
_shelx_estimated_absorpt_T_max   0.712
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4250
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
Bruker APEX2, SAINT and SADABS, version 2011.8-0; Bruker AXS Inc., 
Madison, Wisconsin, USA
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27438
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.932
_diffrn_reflns_theta_max         27.627
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6180
_reflns_number_gt                5459
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS 2012 (Sheldrick, 2012)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-2012 (Sheldrick, 2012)'





_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0178P)²+1.7356P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6180
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0251
_refine_ls_wR_factor_ref         0.0563
_refine_ls_wR_factor_gt          0.0535
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9597(3) 0.6903(2) 0.60326(14) 0.0220(4) Uani 1 1 d . . . . .
C2 C 0.8391(3) 0.6385(2) 0.64278(15) 0.0241(4) Uani 1 1 d . . . . .
H3 H 0.7437 0.6001 0.6055 0.029 Uiso 1 1 calc R U . . .
C3 C 0.8571(3) 0.6425(2) 0.73556(15) 0.0258(5) Uani 1 1 d . . . . .
H4 H 0.7745 0.6084 0.7625 0.031 Uiso 1 1 calc R U . . .
C4 C 0.9989(3) 0.6976(2) 0.78832(14) 0.0234(4) Uani 1 1 d . . . . .
C5 C 1.1199(3) 0.7510(2) 0.75169(15) 0.0273(5) Uani 1 1 d . . . . .
H5 H 1.2154 0.7884 0.7894 0.033 Uiso 1 1 calc R U . . .
C6 C 1.0989(3) 0.7489(2) 0.65849(15) 0.0259(5) Uani 1 1 d . . . . .
H2 H 1.1794 0.7874 0.6320 0.031 Uiso 1 1 calc R U . . .
C7 C 0.9428(3) 0.6859(2) 0.50434(14) 0.0235(4) Uani 1 1 d . . . . .
H6 H 1.0060 0.7448 0.4792 0.028 Uiso 1 1 calc R U . . .
C9 C 0.8386(3) 0.6047(2) 0.35708(14) 0.0211(4) Uani 1 1 d . . . . .
C10 C 0.9642(3) 0.6473(2) 0.31758(14) 0.0231(4) Uani 1 1 d . . . . .
H1 H 1.0628 0.6804 0.3545 0.028 Uiso 1 1 calc R U . . .
C11 C 0.9445(3) 0.6413(2) 0.22496(14) 0.0220(4) Uani 1 1 d . . . . .
C12 C 0.8024(3) 0.5941(2) 0.16699(14) 0.0217(4) Uani 1 1 d . . . . .
C13 C 0.6794(3) 0.5508(2) 0.20802(14) 0.0221(4) Uani 1 1 d . . . . .
C14 C 0.6972(3) 0.5533(2) 0.30072(14) 0.0227(4) Uani 1 1 d . . . . .
H8 H 0.6124 0.5198 0.3262 0.027 Uiso 1 1 calc R U . . .
C21 C 0.6185(3) 0.8753(2) 0.14526(14) 0.0231(4) Uani 1 1 d . . . . .
C22 C 0.5016(3) 0.8313(2) 0.07011(15) 0.0268(5) Uani 1 1 d . . . . .
H9 H 0.4012 0.7960 0.0781 0.032 Uiso 1 1 calc R U . . .
C23 C 0.5307(3) 0.8386(2) -0.01596(15) 0.0268(5) Uani 1 1 d . . . . .
H16 H 0.4516 0.8092 -0.0675 0.032 Uiso 1 1 calc R U . . .
C24 C 0.6780(3) 0.8898(2) -0.02459(14) 0.0244(4) Uani 1 1 d . . . . .
C25 C 0.7979(3) 0.9321(2) 0.04874(15) 0.0293(5) Uani 1 1 d . . . . .
H10 H 0.8988 0.9656 0.0404 0.035 Uiso 1 1 calc R U . . .
C26 C 0.7671(3) 0.9243(2) 0.13394(15) 0.0272(5) Uani 1 1 d . . . . .
H11 H 0.8475 0.9525 0.1852 0.033 Uiso 1 1 calc R U . . .
C27 C 0.5825(3) 0.8667(2) 0.23536(14) 0.0258(5) Uani 1 1 d . . . . .
H15 H 0.4788 0.8352 0.2404 0.031 Uiso 1 1 calc R U . . .
C29 C 0.6452(3) 0.8800(2) 0.39107(14) 0.0218(4) Uani 1 1 d . . . . .
C30 C 0.7332(3) 0.9516(2) 0.46650(15) 0.0245(4) Uani 1 1 d . . . . .
H14 H 0.8158 1.0117 0.4601 0.029 Uiso 1 1 calc R U . . .
C31 C 0.6998(3) 0.9346(2) 0.55091(14) 0.0225(4) Uani 1 1 d . . . . .
C32 C 0.5818(3) 0.8463(2) 0.56351(14) 0.0225(4) Uani 1 1 d . . . . .
C33 C 0.5013(3) 0.7714(2) 0.48772(14) 0.0213(4) Uani 1 1 d . . . . .
C34 C 0.5302(3) 0.7878(2) 0.40286(14) 0.0215(4) Uani 1 1 d . . . . .
H34 H 0.4718 0.7363 0.3524 0.026 Uiso 1 1 calc R U . . .
N1 N 1.0204(3) 0.6994(2) 0.88740(13) 0.0305(4) Uani 1 1 d . . . . .
N8 N 0.8466(2) 0.60602(17) 0.45152(12) 0.0235(4) Uani 1 1 d . . . . .
N21 N 0.7084(3) 0.9037(2) -0.11515(13) 0.0312(4) Uani 1 1 d . . . . .
N28 N 0.6855(2) 0.89999(18) 0.30668(12) 0.0247(4) Uani 1 1 d . . . . .
O1 O 1.1459(2) 0.7459(2) 0.93347(12) 0.0488(5) Uani 1 1 d . . . . .
O2 O 0.9097(2) 0.6546(2) 0.91897(12) 0.0451(5) Uani 1 1 d . . . . .
O3 O 0.7785(2) 0.58536(16) 0.07587(10) 0.0311(4) Uani 1 1 d . . . . .
H3O H 0.8457 0.6116 0.0632 0.037 Uiso 1 1 d R U . . .
O21 O 0.5983(2) 0.8746(2) -0.17936(12) 0.0480(5) Uani 1 1 d . . . . .
O22 O 0.8405(3) 0.9441(2) -0.12359(13) 0.0513(6) Uani 1 1 d . . . . .
O23 O 0.5409(2) 0.82475(16) 0.64290(10) 0.0309(4) Uani 1 1 d . . . . .
H23O H 0.5957 0.8630 0.6834 0.037 Uiso 1 1 d R U . . .
Br1 Br 1.11744(3) 0.69363(3) 0.17138(2) 0.03886(7) Uani 1 1 d . . . . .
Br2 Br 0.48426(3) 0.48466(3) 0.13282(2) 0.03579(7) Uani 1 1 d . . . . .
Br21 Br 0.35575(3) 0.63791(2) 0.50373(2) 0.02752(6) Uani 1 1 d . . . . .
Br22 Br 0.82101(3) 1.03072(2) 0.65327(2) 0.03447(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.397(3) . ?
C1 C6 1.401(3) . ?
C1 C7 1.477(3) . ?
C2 C3 1.384(3) . ?
C2 H3 0.9500 . ?
C3 C4 1.389(3) . ?
C3 H4 0.9500 . ?
C4 C5 1.381(3) . ?
C4 N1 1.477(3) . ?
C5 C6 1.388(3) . ?
C5 H5 0.9500 . ?
C6 H2 0.9500 . ?
C7 N8 1.272(3) . ?
C7 H6 0.9500 . ?
C9 C14 1.396(3) . ?
C9 C10 1.398(3) . ?
C9 N8 1.421(3) . ?
C10 C11 1.379(3) . ?
C10 H1 0.9500 . ?
C11 C12 1.397(3) . ?
C11 Br1 1.899(2) . ?
C12 O3 1.354(2) . ?
C12 C13 1.396(3) . ?
C13 C14 1.383(3) . ?
C13 Br2 1.895(2) . ?
C14 H8 0.9500 . ?
C21 C26 1.393(3) . ?
C21 C22 1.395(3) . ?
C21 C27 1.468(3) . ?
C22 C23 1.385(3) . ?
C22 H9 0.9500 . ?
C23 C24 1.378(3) . ?
C23 H16 0.9500 . ?
C24 C25 1.387(3) . ?
C24 N21 1.464(3) . ?
C25 C26 1.377(3) . ?
C25 H10 0.9500 . ?
C26 H11 0.9500 . ?
C27 N28 1.268(3) . ?
C27 H15 0.9500 . ?
C29 C34 1.394(3) . ?
C29 C30 1.395(3) . ?
C29 N28 1.417(3) . ?
C30 C31 1.387(3) . ?
C30 H14 0.9500 . ?
C31 C32 1.390(3) . ?
C31 Br22 1.893(2) . ?
C32 O23 1.349(3) . ?
C32 C33 1.396(3) . ?
C33 C34 1.379(3) . ?
C33 Br21 1.894(2) . ?
C34 H34 0.9500 . ?
N1 O1 1.218(3) . ?
N1 O2 1.229(3) . ?
N21 O22 1.219(3) . ?
N21 O21 1.222(3) . ?
O3 H3O 0.6916 . ?
O23 H23O 0.7723 . ?

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 C1 C6 119.4(2) . . ?
C2 C1 C7 121.3(2) . . ?
C6 C1 C7 119.3(2) . . ?
C3 C2 C1 120.7(2) . . ?
C3 C2 H3 119.6 . . ?
C1 C2 H3 119.6 . . ?
C2 C3 C4 118.4(2) . . ?
C2 C3 H4 120.8 . . ?
C4 C3 H4 120.8 . . ?
C5 C4 C3 122.5(2) . . ?
C5 C4 N1 118.8(2) . . ?
C3 C4 N1 118.6(2) . . ?
C4 C5 C6 118.5(2) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C5 C6 C1 120.4(2) . . ?
C5 C6 H2 119.8 . . ?
C1 C6 H2 119.8 . . ?
N8 C7 C1 122.4(2) . . ?
N8 C7 H6 118.8 . . ?
C1 C7 H6 118.8 . . ?
C14 C9 C10 118.38(19) . . ?
C14 C9 N8 117.19(19) . . ?
C10 C9 N8 124.40(19) . . ?
C11 C10 C9 119.9(2) . . ?
C11 C10 H1 120.1 . . ?
C9 C10 H1 120.1 . . ?
C10 C11 C12 122.9(2) . . ?
C10 C11 Br1 119.85(16) . . ?
C12 C11 Br1 117.21(16) . . ?
O3 C12 C13 118.99(19) . . ?
O3 C12 C11 124.82(19) . . ?
C13 C12 C11 116.18(19) . . ?
C14 C13 C12 122.1(2) . . ?
C14 C13 Br2 119.81(16) . . ?
C12 C13 Br2 118.10(16) . . ?
C13 C14 C9 120.5(2) . . ?
C13 C14 H8 119.7 . . ?
C9 C14 H8 119.7 . . ?
C26 C21 C22 119.9(2) . . ?
C26 C21 C27 121.3(2) . . ?
C22 C21 C27 118.8(2) . . ?
C23 C22 C21 120.5(2) . . ?
C23 C22 H9 119.8 . . ?
C21 C22 H9 119.8 . . ?
C24 C23 C22 118.0(2) . . ?
C24 C23 H16 121.0 . . ?
C22 C23 H16 121.0 . . ?
C23 C24 C25 123.0(2) . . ?
C23 C24 N21 118.8(2) . . ?
C25 C24 N21 118.2(2) . . ?
C26 C25 C24 118.3(2) . . ?
C26 C25 H10 120.8 . . ?
C24 C25 H10 120.8 . . ?
C25 C26 C21 120.3(2) . . ?
C25 C26 H11 119.9 . . ?
C21 C26 H11 119.9 . . ?
N28 C27 C21 122.1(2) . . ?
N28 C27 H15 118.9 . . ?
C21 C27 H15 118.9 . . ?
C34 C29 C30 118.99(19) . . ?
C34 C29 N28 123.41(19) . . ?
C30 C29 N28 117.5(2) . . ?
C31 C30 C29 119.8(2) . . ?
C31 C30 H14 120.1 . . ?
C29 C30 H14 120.1 . . ?
C30 C31 C32 121.97(19) . . ?
C30 C31 Br22 119.67(17) . . ?
C32 C31 Br22 118.34(16) . . ?
O23 C32 C31 125.70(19) . . ?
O23 C32 C33 117.2(2) . . ?
C31 C32 C33 117.05(19) . . ?
C34 C33 C32 122.1(2) . . ?
C34 C33 Br21 119.35(16) . . ?
C32 C33 Br21 118.49(16) . . ?
C33 C34 C29 119.98(19) . . ?
C33 C34 H34 120.0 . . ?
C29 C34 H34 120.0 . . ?
O1 N1 O2 123.5(2) . . ?
O1 N1 C4 118.4(2) . . ?
O2 N1 C4 118.05(19) . . ?
C7 N8 C9 119.68(19) . . ?
O22 N21 O21 122.9(2) . . ?
O22 N21 C24 119.3(2) . . ?
O21 N21 C24 117.8(2) . . ?
C27 N28 C29 118.6(2) . . ?
C12 O3 H3O 108.8 . . ?
C32 O23 H23O 113.0 . . ?

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 C3 -1.2(3) . . . . ?
C7 C1 C2 C3 179.5(2) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C2 C3 C4 C5 1.7(3) . . . . ?
C2 C3 C4 N1 -178.6(2) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
N1 C4 C5 C6 180.0(2) . . . . ?
C4 C5 C6 C1 -1.8(3) . . . . ?
C2 C1 C6 C5 2.6(3) . . . . ?
C7 C1 C6 C5 -178.1(2) . . . . ?
C2 C1 C7 N8 -21.3(3) . . . . ?
C6 C1 C7 N8 159.4(2) . . . . ?
C14 C9 C10 C11 1.8(3) . . . . ?
N8 C9 C10 C11 179.6(2) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C9 C10 C11 Br1 -177.79(16) . . . . ?
C10 C11 C12 O3 -179.4(2) . . . . ?
Br1 C11 C12 O3 -1.3(3) . . . . ?
C10 C11 C12 C13 -0.9(3) . . . . ?
Br1 C11 C12 C13 177.17(16) . . . . ?
O3 C12 C13 C14 178.1(2) . . . . ?
C11 C12 C13 C14 -0.5(3) . . . . ?
O3 C12 C13 Br2 -1.0(3) . . . . ?
C11 C12 C13 Br2 -179.62(16) . . . . ?
C12 C13 C14 C9 2.6(3) . . . . ?
Br2 C13 C14 C9 -178.34(16) . . . . ?
C10 C9 C14 C13 -3.2(3) . . . . ?
N8 C9 C14 C13 178.86(19) . . . . ?
C26 C21 C22 C23 -1.5(4) . . . . ?
C27 C21 C22 C23 179.6(2) . . . . ?
C21 C22 C23 C24 0.3(4) . . . . ?
C22 C23 C24 C25 1.0(4) . . . . ?
C22 C23 C24 N21 -177.3(2) . . . . ?
C23 C24 C25 C26 -1.1(4) . . . . ?
N21 C24 C25 C26 177.2(2) . . . . ?
C24 C25 C26 C21 -0.2(4) . . . . ?
C22 C21 C26 C25 1.4(4) . . . . ?
C27 C21 C26 C25 -179.7(2) . . . . ?
C26 C21 C27 N28 -1.9(4) . . . . ?
C22 C21 C27 N28 177.0(2) . . . . ?
C34 C29 C30 C31 -3.2(3) . . . . ?
N28 C29 C30 C31 -179.3(2) . . . . ?
C29 C30 C31 C32 1.0(3) . . . . ?
C29 C30 C31 Br22 179.37(17) . . . . ?
C30 C31 C32 O23 -179.3(2) . . . . ?
Br22 C31 C32 O23 2.3(3) . . . . ?
C30 C31 C32 C33 2.3(3) . . . . ?
Br22 C31 C32 C33 -176.13(16) . . . . ?
O23 C32 C33 C34 178.0(2) . . . . ?
C31 C32 C33 C34 -3.4(3) . . . . ?
O23 C32 C33 Br21 -5.1(3) . . . . ?
C31 C32 C33 Br21 173.47(16) . . . . ?
C32 C33 C34 C29 1.3(3) . . . . ?
Br21 C33 C34 C29 -175.58(16) . . . . ?
C30 C29 C34 C33 2.1(3) . . . . ?
N28 C29 C34 C33 177.9(2) . . . . ?
C5 C4 N1 O1 -1.5(3) . . . . ?
C3 C4 N1 O1 178.8(2) . . . . ?
C5 C4 N1 O2 178.0(2) . . . . ?
C3 C4 N1 O2 -1.7(3) . . . . ?
C1 C7 N8 C9 -178.53(19) . . . . ?
C14 C9 N8 C7 -156.4(2) . . . . ?
C10 C9 N8 C7 25.7(3) . . . . ?
C23 C24 N21 O22 -177.1(2) . . . . ?
C25 C24 N21 O22 4.6(3) . . . . ?
C23 C24 N21 O21 3.5(3) . . . . ?
C25 C24 N21 O21 -174.9(2) . . . . ?
C21 C27 N28 C29 -175.4(2) . . . . ?
C34 C29 N28 C27 24.5(3) . . . . ?
C30 C29 N28 C27 -159.6(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3O O2 0.69 2.42 2.944(2) 133.6 1_554
O3 H3O Br1 0.69 2.63 3.0925(16) 126.5 .
O23 H23O O21 0.77 2.08 2.660(2) 132.5 1_556
O23 H23O Br22 0.77 2.68 3.1287(17) 119.3 .

_refine_diff_density_max         0.637
_refine_diff_density_min         -0.743
_refine_diff_density_rms         0.080

_shelxl_version_number           2014/6


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
####################################################################### 
# 
# 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_1b
_database_code_depnum_ccdc_archive 'CCDC 1504722'
_audit_update_record             
;
2016-09-16 deposited with the CCDC.
2016-10-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        
;
(E)--2,6--Diphenyl--4--(4--nitrostyryl)phenol
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H19 N O3'
_chemical_formula_sum            'C26 H19 N O3'
_chemical_formula_weight         393.42

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   11.8923(3)
_cell_length_b                   12.9590(3)
_cell_length_c                   12.7118(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.6380(10)
_cell_angle_gamma                90
_cell_volume                     1941.66(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    8187
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      29.94

_exptl_crystal_description       plate-like
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9656
_exptl_absorpt_correction_T_max  0.9965
_exptl_absorpt_process_details   
;
Bruker APEX2, SAINT and SADABS, version 2011.8-0; Bruker AXS Inc., 
Madison, Wisconsin, USA
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31205
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.728
_diffrn_reflns_theta_max         30.109
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5706
_reflns_number_gt                4257
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
?
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0753P)²+0.5969P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5706
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1442
_refine_ls_wR_factor_gt          0.1296
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.09377(11) -0.10308(10) -0.10286(10) 0.0279(3) Uani 1 1 d . . . . .
C2 C 0.06099(13) -0.20345(11) -0.13238(11) 0.0339(3) Uani 1 1 d . . . . .
H2 H 0.071983 -0.257145 -0.081163 0.041 Uiso 1 1 calc R U . . .
C3 C 0.01286(13) -0.22625(11) -0.23468(11) 0.0345(3) Uani 1 1 d . . . . .
H3 H -0.011270 -0.294465 -0.253460 0.041 Uiso 1 1 calc R U . . .
C4 C 0.00046(11) -0.14802(11) -0.30920(10) 0.0295(3) Uani 1 1 d . . . . .
C5 C 0.03740(13) -0.04819(11) -0.28506(10) 0.0340(3) Uani 1 1 d . . . . .
H5 H 0.030981 0.004006 -0.337998 0.041 Uiso 1 1 calc R U . . .
C6 C 0.08393(13) -0.02675(11) -0.18154(11) 0.0338(3) Uani 1 1 d . . . . .
H6 H 0.109697 0.041184 -0.163576 0.041 Uiso 1 1 calc R U . . .
C7 C 0.13755(11) -0.08218(10) 0.00865(10) 0.0295(3) Uani 1 1 d . . . . .
H7 H 0.149215 -0.139755 0.055075 0.035 Uiso 1 1 calc R U . . .
C8 C 0.16220(11) 0.01058(11) 0.05001(10) 0.0289(3) Uani 1 1 d . . . . .
H8 H 0.144868 0.067871 0.004083 0.035 Uiso 1 1 calc R U . . .
C9 C 0.21317(10) 0.03415(10) 0.15869(9) 0.0257(2) Uani 1 1 d . . . . .
C10 C 0.25085(11) 0.13453(10) 0.18132(9) 0.0266(2) Uani 1 1 d . . . . .
H10 H 0.236148 0.185734 0.127777 0.032 Uiso 1 1 calc R U . . .
C11 C 0.30934(10) 0.16275(10) 0.27960(9) 0.0250(2) Uani 1 1 d . . . . .
C12 C 0.32921(11) 0.08644(10) 0.35831(9) 0.0256(2) Uani 1 1 d . . . . .
C13 C 0.28573(11) -0.01399(10) 0.34090(9) 0.0252(2) Uani 1 1 d . . . . .
C14 C 0.22926(11) -0.03862(10) 0.24098(9) 0.0263(2) Uani 1 1 d . . . . .
H14 H 0.200842 -0.106617 0.228200 0.032 Uiso 1 1 calc R U . . .
C15A C 0.35245(11) 0.27027(10) 0.29618(9) 0.0259(2) Uani 1 1 d . . . . .
C15B C 0.30560(11) -0.09458(10) 0.42491(9) 0.0261(2) Uani 1 1 d . . . . .
C16A C 0.39901(12) 0.32085(11) 0.21509(10) 0.0315(3) Uani 1 1 d . . . . .
H16A H 0.403094 0.285815 0.150060 0.038 Uiso 1 1 calc R U . . .
C16B C 0.28430(13) -0.07624(11) 0.52858(10) 0.0334(3) Uani 1 1 d . . . . .
H16B H 0.254422 -0.011550 0.546496 0.040 Uiso 1 1 calc R U . . .
C17A C 0.43937(13) 0.42098(11) 0.22743(12) 0.0360(3) Uani 1 1 d . . . . .
H17A H 0.469766 0.454259 0.170876 0.043 Uiso 1 1 calc R U . . .
C17B C 0.30666(14) -0.15246(12) 0.60609(11) 0.0375(3) Uani 1 1 d . . . . .
H17B H 0.291410 -0.139451 0.676374 0.045 Uiso 1 1 calc R U . . .
C18A C 0.43538(13) 0.47247(11) 0.32216(12) 0.0381(3) Uani 1 1 d . . . . .
H18A H 0.464977 0.540423 0.331553 0.046 Uiso 1 1 calc R U . . .
C18B C 0.35081(13) -0.24670(11) 0.58141(11) 0.0363(3) Uani 1 1 d . . . . .
H18B H 0.368129 -0.297600 0.634894 0.044 Uiso 1 1 calc R U . . .
C19A C 0.38806(13) 0.42462(11) 0.40331(12) 0.0368(3) Uani 1 1 d . . . . .
H19A H 0.384115 0.460367 0.467957 0.044 Uiso 1 1 calc R U . . .
C19B C 0.36959(13) -0.26635(11) 0.47822(12) 0.0353(3) Uani 1 1 d . . . . .
H19B H 0.398342 -0.331551 0.460435 0.042 Uiso 1 1 calc R U . . .
C20A C 0.34638(12) 0.32469(11) 0.39062(10) 0.0312(3) Uani 1 1 d . . . . .
H20A H 0.313407 0.292848 0.446493 0.037 Uiso 1 1 calc R U . . .
C20B C 0.34660(12) -0.19119(10) 0.40057(10) 0.0306(3) Uani 1 1 d . . . . .
H20B H 0.358994 -0.205831 0.329788 0.037 Uiso 1 1 calc R U . . .
N1 N -0.05472(11) -0.17101(10) -0.41626(9) 0.0364(3) Uani 1 1 d . . . . .
O1 O -0.06374(13) -0.10263(10) -0.48283(9) 0.0602(4) Uani 1 1 d . . . . .
O2 O -0.09006(12) -0.25892(10) -0.43506(9) 0.0542(3) Uani 1 1 d . . . . .
O3 O 0.39542(9) 0.10521(8) 0.45306(7) 0.0362(2) Uani 1 1 d . . . . .
H1O H 0.436561 0.159464 0.446502 0.054 Uiso 1 1 d R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3949(19) . ?
C1 C6 1.4005(19) . ?
C1 C7 1.4688(17) . ?
C2 C3 1.3813(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.382(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.3874(19) . ?
C4 N1 1.4608(16) . ?
C5 C6 1.3863(18) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.3290(19) . ?
C7 H7 0.9500 . ?
C8 C9 1.4651(16) . ?
C8 H8 0.9500 . ?
C9 C10 1.3933(18) . ?
C9 C14 1.4025(17) . ?
C10 C11 1.3955(16) . ?
C10 H10 0.9500 . ?
C11 C12 1.4043(17) . ?
C11 C15A 1.4899(17) . ?
C12 O3 1.3703(14) . ?
C12 C13 1.4070(17) . ?
C13 C14 1.3927(16) . ?
C13 C15B 1.4899(16) . ?
C14 H14 0.9500 . ?
C15A C16A 1.3965(18) . ?
C15A C20A 1.4025(17) . ?
C15B C20B 1.3932(19) . ?
C15B C16B 1.3950(18) . ?
C16A C17A 1.385(2) . ?
C16A H16A 0.9500 . ?
C16B C17B 1.3956(19) . ?
C16B H16B 0.9500 . ?
C17A C18A 1.383(2) . ?
C17A H17A 0.9500 . ?
C17B C18B 1.382(2) . ?
C17B H17B 0.9500 . ?
C18A C19A 1.386(2) . ?
C18A H18A 0.9500 . ?
C18B C19B 1.383(2) . ?
C18B H18B 0.9500 . ?
C19A C20A 1.388(2) . ?
C19A H19A 0.9500 . ?
C19B C20B 1.3879(19) . ?
C19B H19B 0.9500 . ?
C20A H20A 0.9500 . ?
C20B H20B 0.9500 . ?
N1 O1 1.2202(18) . ?
N1 O2 1.2268(17) . ?
O3 H1O 0.8669 . ?

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 C1 C6 118.20(12) . . ?
C2 C1 C7 118.83(12) . . ?
C6 C1 C7 122.97(12) . . ?
C3 C2 C1 121.25(13) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 118.78(13) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C3 C4 C5 122.05(12) . . ?
C3 C4 N1 118.86(12) . . ?
C5 C4 N1 119.08(12) . . ?
C6 C5 C4 118.13(13) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
C5 C6 C1 121.42(13) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
C8 C7 C1 125.44(12) . . ?
C8 C7 H7 117.3 . . ?
C1 C7 H7 117.3 . . ?
C7 C8 C9 127.11(12) . . ?
C7 C8 H8 116.4 . . ?
C9 C8 H8 116.4 . . ?
C10 C9 C14 117.74(11) . . ?
C10 C9 C8 118.08(11) . . ?
C14 C9 C8 124.16(12) . . ?
C9 C10 C11 122.54(11) . . ?
C9 C10 H10 118.7 . . ?
C11 C10 H10 118.7 . . ?
C10 C11 C12 118.03(11) . . ?
C10 C11 C15A 119.53(11) . . ?
C12 C11 C15A 122.38(11) . . ?
O3 C12 C11 121.60(11) . . ?
O3 C12 C13 117.30(10) . . ?
C11 C12 C13 121.05(11) . . ?
C14 C13 C12 118.56(11) . . ?
C14 C13 C15B 120.29(11) . . ?
C12 C13 C15B 121.04(10) . . ?
C13 C14 C9 121.84(12) . . ?
C13 C14 H14 119.1 . . ?
C9 C14 H14 119.1 . . ?
C16A C15A C20A 117.80(12) . . ?
C16A C15A C11 119.82(11) . . ?
C20A C15A C11 122.37(11) . . ?
C20B C15B C16B 118.40(12) . . ?
C20B C15B C13 119.84(11) . . ?
C16B C15B C13 121.75(12) . . ?
C17A C16A C15A 121.43(12) . . ?
C17A C16A H16A 119.3 . . ?
C15A C16A H16A 119.3 . . ?
C15B C16B C17B 120.33(13) . . ?
C15B C16B H16B 119.8 . . ?
C17B C16B H16B 119.8 . . ?
C18A C17A C16A 119.94(13) . . ?
C18A C17A H17A 120.0 . . ?
C16A C17A H17A 120.0 . . ?
C18B C17B C16B 120.51(13) . . ?
C18B C17B H17B 119.7 . . ?
C16B C17B H17B 119.7 . . ?
C17A C18A C19A 119.78(13) . . ?
C17A C18A H18A 120.1 . . ?
C19A C18A H18A 120.1 . . ?
C17B C18B C19B 119.48(13) . . ?
C17B C18B H18B 120.3 . . ?
C19B C18B H18B 120.3 . . ?
C18A C19A C20A 120.34(13) . . ?
C18A C19A H19A 119.8 . . ?
C20A C19A H19A 119.8 . . ?
C18B C19B C20B 120.26(14) . . ?
C18B C19B H19B 119.9 . . ?
C20B C19B H19B 119.9 . . ?
C19A C20A C15A 120.68(13) . . ?
C19A C20A H20A 119.7 . . ?
C15A C20A H20A 119.7 . . ?
C19B C20B C15B 120.96(13) . . ?
C19B C20B H20B 119.5 . . ?
C15B C20B H20B 119.5 . . ?
O1 N1 O2 122.89(12) . . ?
O1 N1 C4 119.03(12) . . ?
O2 N1 C4 118.09(13) . . ?
C12 O3 H1O 109.0 . . ?

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 C3 -4.4(2) . . . . ?
C7 C1 C2 C3 176.02(13) . . . . ?
C1 C2 C3 C4 1.9(2) . . . . ?
C2 C3 C4 C5 1.7(2) . . . . ?
C2 C3 C4 N1 -177.47(13) . . . . ?
C3 C4 C5 C6 -2.6(2) . . . . ?
N1 C4 C5 C6 176.55(13) . . . . ?
C4 C5 C6 C1 0.0(2) . . . . ?
C2 C1 C6 C5 3.4(2) . . . . ?
C7 C1 C6 C5 -177.00(13) . . . . ?
C2 C1 C7 C8 -173.59(14) . . . . ?
C6 C1 C7 C8 6.8(2) . . . . ?
C1 C7 C8 C9 -175.46(12) . . . . ?
C7 C8 C9 C10 168.74(13) . . . . ?
C7 C8 C9 C14 -9.5(2) . . . . ?
C14 C9 C10 C11 4.05(19) . . . . ?
C8 C9 C10 C11 -174.31(12) . . . . ?
C9 C10 C11 C12 -0.74(19) . . . . ?
C9 C10 C11 C15A 176.74(12) . . . . ?
C10 C11 C12 O3 173.50(12) . . . . ?
C15A C11 C12 O3 -3.90(19) . . . . ?
C10 C11 C12 C13 -3.68(19) . . . . ?
C15A C11 C12 C13 178.92(12) . . . . ?
O3 C12 C13 C14 -172.71(12) . . . . ?
C11 C12 C13 C14 4.59(19) . . . . ?
O3 C12 C13 C15B 3.48(18) . . . . ?
C11 C12 C13 C15B -179.22(12) . . . . ?
C12 C13 C14 C9 -1.12(19) . . . . ?
C15B C13 C14 C9 -177.34(12) . . . . ?
C10 C9 C14 C13 -3.09(19) . . . . ?
C8 C9 C14 C13 175.16(12) . . . . ?
C10 C11 C15A C16A -39.38(17) . . . . ?
C12 C11 C15A C16A 137.98(13) . . . . ?
C10 C11 C15A C20A 139.40(13) . . . . ?
C12 C11 C15A C20A -43.23(18) . . . . ?
C14 C13 C15B C20B 46.15(18) . . . . ?
C12 C13 C15B C20B -129.97(13) . . . . ?
C14 C13 C15B C16B -133.90(14) . . . . ?
C12 C13 C15B C16B 49.98(18) . . . . ?
C20A C15A C16A C17A 0.8(2) . . . . ?
C11 C15A C16A C17A 179.65(12) . . . . ?
C20B C15B C16B C17B 1.7(2) . . . . ?
C13 C15B C16B C17B -178.29(13) . . . . ?
C15A C16A C17A C18A 0.9(2) . . . . ?
C15B C16B C17B C18B 0.4(2) . . . . ?
C16A C17A C18A C19A -1.8(2) . . . . ?
C16B C17B C18B C19B -2.0(2) . . . . ?
C17A C18A C19A C20A 1.1(2) . . . . ?
C17B C18B C19B C20B 1.4(2) . . . . ?
C18A C19A C20A C15A 0.6(2) . . . . ?
C16A C15A C20A C19A -1.5(2) . . . . ?
C11 C15A C20A C19A 179.64(13) . . . . ?
C18B C19B C20B C15B 0.7(2) . . . . ?
C16B C15B C20B C19B -2.2(2) . . . . ?
C13 C15B C20B C19B 177.71(12) . . . . ?
C3 C4 N1 O1 -178.53(15) . . . . ?
C5 C4 N1 O1 2.3(2) . . . . ?
C3 C4 N1 O2 1.5(2) . . . . ?
C5 C4 N1 O2 -177.68(14) . . . . ?

_refine_diff_density_max         0.366
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.048


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
####################################################################### 
# 
# 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_2e
_database_code_depnum_ccdc_archive 'CCDC 1504723'
_audit_update_record             
;
2016-09-16 deposited with the CCDC.
2016-10-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        
(E)--4--(4--Nitrophenylmethylenimino)--2,6--dichlorophenol
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 Cl2 N2 O4'
_chemical_formula_sum            'C13 H10 Cl2 N2 O4'
_chemical_formula_weight         329.13

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.7179(3)
_cell_length_b                   13.5770(5)
_cell_length_c                   11.6351(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.5550(10)
_cell_angle_gamma                90
_cell_volume                     1368.16(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    6646
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      30.52

_exptl_crystal_description       Block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.491
_shelx_estimated_absorpt_T_min   0.875
_shelx_estimated_absorpt_T_max   0.943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8747
_exptl_absorpt_correction_T_max  0.9434
_exptl_absorpt_process_details   
;
Bruker APEX2, SAINT and SADABS, version 2011.8-0; Bruker AXS Inc., 
Madison, Wisconsin, USA
;
_exptl_absorpt_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14171
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.314
_diffrn_reflns_theta_max         30.518
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4177
_reflns_number_gt                3540
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'


_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0504P)²+0.5913P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4177
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.1000
_refine_ls_wR_factor_gt          0.0935
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.45352(14) 0.63791(9) 0.33466(10) 0.0221(2) Uani 1 1 d . . . . .
C2 C 0.41145(14) 0.73242(9) 0.36651(11) 0.0256(2) Uani 1 1 d . . . . .
H2 H 0.3371 0.7406 0.4194 0.031 Uiso 1 1 calc R U . . .
C3 C 0.47789(15) 0.81449(9) 0.32116(11) 0.0262(2) Uani 1 1 d . . . . .
H3 H 0.4479 0.8791 0.3406 0.031 Uiso 1 1 calc R U . . .
C4 C 0.58860(14) 0.79995(9) 0.24707(11) 0.0244(2) Uani 1 1 d . . . . .
C5 C 0.63529(15) 0.70715(10) 0.21528(11) 0.0270(2) Uani 1 1 d . . . . .
H5 H 0.7126 0.6996 0.1647 0.032 Uiso 1 1 calc R U . . .
C6 C 0.56584(14) 0.62591(9) 0.25943(11) 0.0258(2) Uani 1 1 d . . . . .
H6 H 0.5949 0.5615 0.2383 0.031 Uiso 1 1 calc R U . . .
C7 C 0.38220(14) 0.55212(9) 0.38468(10) 0.0242(2) Uani 1 1 d . . . . .
H7 H 0.3341 0.5599 0.4534 0.029 Uiso 1 1 calc R U . . .
C9 C 0.31991(14) 0.38486(9) 0.38869(10) 0.0215(2) Uani 1 1 d . . . . .
C10 C 0.37959(15) 0.29391(9) 0.36133(10) 0.0238(2) Uani 1 1 d . . . . .
H10 H 0.4583 0.2905 0.3114 0.029 Uiso 1 1 calc R U . . .
C11 C 0.32460(15) 0.20840(9) 0.40667(11) 0.0238(2) Uani 1 1 d . . . . .
C12 C 0.20624(14) 0.20943(9) 0.47795(10) 0.0226(2) Uani 1 1 d . . . . .
C13 C 0.14853(14) 0.30206(9) 0.50400(10) 0.0226(2) Uani 1 1 d . . . . .
C14 C 0.20307(14) 0.38903(9) 0.46132(10) 0.0228(2) Uani 1 1 d . . . . .
H14 H 0.1616 0.4506 0.4812 0.027 Uiso 1 1 calc R U . . .
N1 N 0.66092(14) 0.88667(9) 0.20060(11) 0.0333(3) Uani 1 1 d . . . . .
N8 N 0.38390(12) 0.46772(8) 0.33729(9) 0.0242(2) Uani 1 1 d . . . . .
O1 O 0.76808(15) 0.87358(10) 0.14308(12) 0.0510(3) Uani 1 1 d . . . . .
O2 O 0.61143(17) 0.96786(8) 0.22024(15) 0.0587(4) Uani 1 1 d . . . . .
O1W O 0.87943(16) 0.06999(10) 0.59022(11) 0.0519(3) Uani 1 1 d . . . . .
H1W H 0.8542 0.0161 0.5527 0.078 Uiso 1 1 d R U . . .
H2W H 0.8992 0.0507 0.6675 0.078 Uiso 1 1 d R U . . .
O3 O 0.15499(11) 0.12470(7) 0.52044(8) 0.0296(2) Uani 1 1 d . . . . .
H3O H 0.0639 0.1301 0.5411 0.035 Uiso 1 1 d R U . . .
Cl1 Cl 0.40751(5) 0.09752(2) 0.37519(4) 0.03886(11) Uani 1 1 d . . . . .
Cl2 Cl 0.00269(4) 0.30770(3) 0.59303(3) 0.03529(10) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.3955(17) . ?
C1 C2 1.3962(17) . ?
C1 C7 1.4712(16) . ?
C2 C3 1.3875(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.3797(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.3871(18) . ?
C4 N1 1.4677(16) . ?
C5 C6 1.3850(17) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N8 1.2725(16) . ?
C7 H7 0.9500 . ?
C9 C10 1.3909(17) . ?
C9 C14 1.3969(16) . ?
C9 N8 1.4179(15) . ?
C10 C11 1.3834(16) . ?
C10 H10 0.9500 . ?
C11 C12 1.3958(17) . ?
C11 Cl1 1.7273(12) . ?
C12 O3 1.3483(14) . ?
C12 C13 1.4005(17) . ?
C13 C14 1.3860(16) . ?
C13 Cl2 1.7310(12) . ?
C14 H14 0.9500 . ?
N1 O2 1.2149(18) . ?
N1 O1 1.2227(17) . ?
O1W H1W 0.8671 . ?
O1W H2W 0.9339 . ?
O3 H3O 0.8585 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 119.88(11) . . ?
C6 C1 C7 120.94(11) . . ?
C2 C1 C7 119.14(11) . . ?
C3 C2 C1 120.23(11) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 118.35(11) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C3 C4 C5 122.96(11) . . ?
C3 C4 N1 118.42(11) . . ?
C5 C4 N1 118.62(12) . . ?
C6 C5 C4 118.07(11) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
C5 C6 C1 120.49(12) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
N8 C7 C1 121.01(11) . . ?
N8 C7 H7 119.5 . . ?
C1 C7 H7 119.5 . . ?
C10 C9 C14 119.48(10) . . ?
C10 C9 N8 115.62(10) . . ?
C14 C9 N8 124.90(11) . . ?
C11 C10 C9 120.19(11) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 122.01(11) . . ?
C10 C11 Cl1 118.62(10) . . ?
C12 C11 Cl1 119.37(9) . . ?
O3 C12 C11 120.51(11) . . ?
O3 C12 C13 123.00(11) . . ?
C11 C12 C13 116.47(10) . . ?
C14 C13 C12 122.76(11) . . ?
C14 C13 Cl2 118.83(9) . . ?
C12 C13 Cl2 118.41(9) . . ?
C13 C14 C9 119.07(11) . . ?
C13 C14 H14 120.5 . . ?
C9 C14 H14 120.5 . . ?
O2 N1 O1 123.01(13) . . ?
O2 N1 C4 118.81(12) . . ?
O1 N1 C4 118.18(12) . . ?
C7 N8 C9 120.47(10) . . ?
H1W O1W H2W 104.9 . . ?
C12 O3 H3O 112.7 . . ?

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 C3 1.75(19) . . . . ?
C7 C1 C2 C3 179.54(12) . . . . ?
C1 C2 C3 C4 -1.76(19) . . . . ?
C2 C3 C4 C5 0.6(2) . . . . ?
C2 C3 C4 N1 -178.96(11) . . . . ?
C3 C4 C5 C6 0.7(2) . . . . ?
N1 C4 C5 C6 -179.81(11) . . . . ?
C4 C5 C6 C1 -0.70(19) . . . . ?
C2 C1 C6 C5 -0.49(19) . . . . ?
C7 C1 C6 C5 -178.24(12) . . . . ?
C6 C1 C7 N8 -21.15(18) . . . . ?
C2 C1 C7 N8 161.08(12) . . . . ?
C14 C9 C10 C11 -0.62(18) . . . . ?
N8 C9 C10 C11 -179.77(11) . . . . ?
C9 C10 C11 C12 1.73(19) . . . . ?
C9 C10 C11 Cl1 -177.37(9) . . . . ?
C10 C11 C12 O3 179.80(11) . . . . ?
Cl1 C11 C12 O3 -1.10(16) . . . . ?
C10 C11 C12 C13 -1.71(18) . . . . ?
Cl1 C11 C12 C13 177.39(9) . . . . ?
O3 C12 C13 C14 179.11(11) . . . . ?
C11 C12 C13 C14 0.66(18) . . . . ?
O3 C12 C13 Cl2 -1.03(17) . . . . ?
C11 C12 C13 Cl2 -179.48(9) . . . . ?
C12 C13 C14 C9 0.36(18) . . . . ?
Cl2 C13 C14 C9 -179.49(9) . . . . ?
C10 C9 C14 C13 -0.39(18) . . . . ?
N8 C9 C14 C13 178.67(11) . . . . ?
C3 C4 N1 O2 -6.6(2) . . . . ?
C5 C4 N1 O2 173.85(14) . . . . ?
C3 C4 N1 O1 173.82(13) . . . . ?
C5 C4 N1 O1 -5.72(19) . . . . ?
C1 C7 N8 C9 177.62(11) . . . . ?
C10 C9 N8 C7 -154.69(12) . . . . ?
C14 C9 N8 C7 26.22(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1W O3 0.87 2.09 2.9405(17) 166.4 3_656
O1W H1W Cl1 0.87 2.95 3.4383(15) 117.2 3_656
O1W H2W N8 0.93 2.01 2.9158(16) 162.9 4_666
O3 H3O O1W 0.86 1.95 2.7252(16) 150.2 1_455
O3 H3O Cl2 0.86 2.56 2.9842(10) 111.8 .

_refine_diff_density_max         0.511
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.053

_shelxl_version_number           2014/6


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# 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_2h
_database_code_depnum_ccdc_archive 'CCDC 1504724'
_audit_update_record             
;
2016-09-16 deposited with the CCDC.
2016-10-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_chemical_name_systematic        
'(E)--4--(2,4--Dinitrophenylmethylenimino)--2,6--dimethylphenol (2h)'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H13 N3 O5'
_chemical_formula_sum            'C15 H13 N3 O5'
_chemical_formula_weight         315.28

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

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.6932(4)
_cell_length_b                   7.6756(5)
_cell_length_c                   15.1649(9)
_cell_angle_alpha                86.795(2)
_cell_angle_beta                 85.596(2)
_cell_angle_gamma                68.438(2)
_cell_volume                     722.10(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4027
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      27.51

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.111
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7172
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
Bruker APEX2, SAINT and SADABS, version 2011.8-0; Bruker AXS Inc., 
Madison, Wisconsin, USA
;


_exptl_absorpt_special_details   ?


_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13077
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.347
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2612
_reflns_number_gt                1985
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick,2013)'



_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0485P)²+0.2371P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2612
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.1022
_refine_ls_wR_factor_gt          0.0934
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2489(2) 0.4996(2) 0.48089(10) 0.0218(3) Uani 1 1 d . . . . .
C6 C 0.3120(3) 0.3091(2) 0.46297(10) 0.0262(4) Uani 1 1 d . . . . .
H6 H 0.3369 0.2206 0.5111 0.031 Uiso 1 1 calc R U . . .
C5 C 0.3392(3) 0.2456(2) 0.37808(10) 0.0289(4) Uani 1 1 d . . . . .
H5 H 0.3866 0.1153 0.3677 0.035 Uiso 1 1 calc R U . . .
C4 C 0.2960(2) 0.3755(2) 0.30826(10) 0.0248(4) Uani 1 1 d . . . . .
C3 C 0.2272(2) 0.5648(2) 0.32127(10) 0.0258(4) Uani 1 1 d . . . . .
H3 H 0.1931 0.6527 0.2729 0.031 Uiso 1 1 calc R U . . .
C2 C 0.2091(2) 0.6227(2) 0.40692(10) 0.0236(3) Uani 1 1 d . . . . .
C7 C 0.2188(2) 0.5594(2) 0.57312(10) 0.0241(3) Uani 1 1 d . . . . .
H7 H 0.1522 0.6885 0.5860 0.029 Uiso 1 1 calc R U . . .
C9 C 0.2547(2) 0.4923(2) 0.72493(10) 0.0238(4) Uani 1 1 d . . . . .
C10 C 0.3203(3) 0.3477(2) 0.78851(10) 0.0253(4) Uani 1 1 d . . . . .
H10 H 0.3774 0.2216 0.7701 0.030 Uiso 1 1 calc R U . . .
C11 C 0.3043(3) 0.3831(2) 0.87813(10) 0.0258(4) Uani 1 1 d . . . . .
C12 C 0.2178(3) 0.5699(2) 0.90339(10) 0.0260(4) Uani 1 1 d . . . . .
C13 C 0.1518(3) 0.7191(2) 0.84120(10) 0.0266(4) Uani 1 1 d . . . . .
C14 C 0.1721(3) 0.6775(2) 0.75283(10) 0.0268(4) Uani 1 1 d . . . . .
H14 H 0.1290 0.7770 0.7099 0.032 Uiso 1 1 calc R U . . .
C15 C 0.3803(3) 0.2269(2) 0.94667(11) 0.0352(4) Uani 1 1 d . . . . .
H15A H 0.4908 0.2446 0.9801 0.053 Uiso 1 1 calc R U . . .
H15B H 0.4411 0.1064 0.9173 0.053 Uiso 1 1 calc R U . . .
H15C H 0.2585 0.2281 0.9872 0.053 Uiso 1 1 calc R U . . .
C16 C 0.0626(3) 0.9192(2) 0.87082(11) 0.0395(5) Uani 1 1 d . . . . .
H16A H 0.1613 0.9384 0.9104 0.059 Uiso 1 1 calc R U . . .
H16B H -0.0782 0.9445 0.9023 0.059 Uiso 1 1 calc R U . . .
H16C H 0.0469 1.0044 0.8190 0.059 Uiso 1 1 calc R U . . .
N1 N 0.1516(3) 0.8254(2) 0.41570(9) 0.0392(4) Uani 1 1 d . . . . .
N2 N 0.3241(2) 0.3120(2) 0.21695(9) 0.0320(3) Uani 1 1 d . . . . .
N8 N 0.2822(2) 0.43787(18) 0.63562(8) 0.0268(3) Uani 1 1 d . . . . .
O1 O 0.0320(4) 0.9284(2) 0.36319(10) 0.0947(8) Uani 1 1 d . . . . .
O2 O 0.2298(2) 0.88109(17) 0.47320(9) 0.0463(4) Uani 1 1 d . . . . .
O3 O 0.2788(2) 0.43228(18) 0.15743(7) 0.0426(3) Uani 1 1 d . . . . .
O4 O 0.3908(2) 0.14354(19) 0.20500(8) 0.0486(4) Uani 1 1 d . . . . .
O5 O 0.1950(2) 0.61870(17) 0.98991(7) 0.0383(3) Uani 1 1 d . . . . .
H5O H 0.2378 0.5232 1.0196 0.057 Uiso 1 1 d R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.401(2) . ?
C1 C2 1.402(2) . ?
C1 C7 1.473(2) . ?
C6 C5 1.377(2) . ?
C6 H6 0.9500 . ?
C5 C4 1.385(2) . ?
C5 H5 0.9500 . ?
C4 C3 1.374(2) . ?
C4 N2 1.469(2) . ?
C3 C2 1.379(2) . ?
C3 H3 0.9500 . ?
C2 N1 1.470(2) . ?
C7 N8 1.2730(19) . ?
C7 H7 0.9500 . ?
C9 C10 1.393(2) . ?
C9 C14 1.400(2) . ?
C9 N8 1.4181(19) . ?
C10 C11 1.389(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.399(2) . ?
C11 C15 1.507(2) . ?
C12 O5 1.3663(18) . ?
C12 C13 1.403(2) . ?
C13 C14 1.380(2) . ?
C13 C16 1.509(2) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
N1 O1 1.2092(19) . ?
N1 O2 1.2221(19) . ?
N2 O4 1.2218(18) . ?
N2 O3 1.2257(18) . ?
O5 H5O 0.8067 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 115.74(14) . . ?
C6 C1 C7 119.91(13) . . ?
C2 C1 C7 124.29(14) . . ?
C5 C6 C1 122.39(14) . . ?
C5 C6 H6 118.8 . . ?
C1 C6 H6 118.8 . . ?
C6 C5 C4 118.60(15) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C3 C4 C5 122.01(14) . . ?
C3 C4 N2 118.13(14) . . ?
C5 C4 N2 119.86(14) . . ?
C4 C3 C2 117.71(14) . . ?
C4 C3 H3 121.1 . . ?
C2 C3 H3 121.1 . . ?
C3 C2 C1 123.47(14) . . ?
C3 C2 N1 114.98(13) . . ?
C1 C2 N1 121.51(13) . . ?
N8 C7 C1 119.91(14) . . ?
N8 C7 H7 120.0 . . ?
C1 C7 H7 120.0 . . ?
C10 C9 C14 118.60(14) . . ?
C10 C9 N8 116.28(14) . . ?
C14 C9 N8 125.11(14) . . ?
C11 C10 C9 121.73(15) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C10 C11 C12 117.90(14) . . ?
C10 C11 C15 121.71(14) . . ?
C12 C11 C15 120.39(14) . . ?
O5 C12 C11 122.19(14) . . ?
O5 C12 C13 115.85(14) . . ?
C11 C12 C13 121.95(14) . . ?
C14 C13 C12 118.17(14) . . ?
C14 C13 C16 121.37(14) . . ?
C12 C13 C16 120.47(14) . . ?
C13 C14 C9 121.65(14) . . ?
C13 C14 H14 119.2 . . ?
C9 C14 H14 119.2 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O1 N1 O2 123.49(16) . . ?
O1 N1 C2 117.27(15) . . ?
O2 N1 C2 119.22(14) . . ?
O4 N2 O3 124.16(14) . . ?
O4 N2 C4 118.30(14) . . ?
O3 N2 C4 117.53(14) . . ?
C7 N8 C9 120.87(14) . . ?
C12 O5 H5O 107.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 C6 C5 1.7(2) . . . . ?
C7 C1 C6 C5 178.95(15) . . . . ?
C1 C6 C5 C4 -2.1(2) . . . . ?
C6 C5 C4 C3 0.0(2) . . . . ?
C6 C5 C4 N2 179.84(14) . . . . ?
C5 C4 C3 C2 2.3(2) . . . . ?
N2 C4 C3 C2 -177.58(14) . . . . ?
C4 C3 C2 C1 -2.7(2) . . . . ?
C4 C3 C2 N1 175.31(14) . . . . ?
C6 C1 C2 C3 0.7(2) . . . . ?
C7 C1 C2 C3 -176.39(15) . . . . ?
C6 C1 C2 N1 -177.13(15) . . . . ?
C7 C1 C2 N1 5.8(2) . . . . ?
C6 C1 C7 N8 11.1(2) . . . . ?
C2 C1 C7 N8 -171.90(15) . . . . ?
C14 C9 C10 C11 0.4(2) . . . . ?
N8 C9 C10 C11 179.12(14) . . . . ?
C9 C10 C11 C12 0.6(2) . . . . ?
C9 C10 C11 C15 -178.47(15) . . . . ?
C10 C11 C12 O5 179.79(14) . . . . ?
C15 C11 C12 O5 -1.1(2) . . . . ?
C10 C11 C12 C13 -1.2(2) . . . . ?
C15 C11 C12 C13 177.92(15) . . . . ?
O5 C12 C13 C14 179.79(14) . . . . ?
C11 C12 C13 C14 0.7(2) . . . . ?
O5 C12 C13 C16 0.2(2) . . . . ?
C11 C12 C13 C16 -178.95(16) . . . . ?
C12 C13 C14 C9 0.4(2) . . . . ?
C16 C13 C14 C9 -179.99(16) . . . . ?
C10 C9 C14 C13 -0.9(2) . . . . ?
N8 C9 C14 C13 -179.49(15) . . . . ?
C3 C2 N1 O1 34.3(2) . . . . ?
C1 C2 N1 O1 -147.70(18) . . . . ?
C3 C2 N1 O2 -143.82(16) . . . . ?
C1 C2 N1 O2 34.2(2) . . . . ?
C3 C4 N2 O4 178.07(15) . . . . ?
C5 C4 N2 O4 -1.8(2) . . . . ?
C3 C4 N2 O3 -1.9(2) . . . . ?
C5 C4 N2 O3 178.25(15) . . . . ?
C1 C7 N8 C9 -179.94(13) . . . . ?
C10 C9 N8 C7 177.03(15) . . . . ?
C14 C9 N8 C7 -4.4(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H5O O3 0.81 2.17 2.8353(16) 139.7 1_556

_refine_diff_density_max         0.171
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.038

_shelxl_version_number           2014/6


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
