# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1814043'
_audit_update_record             
;
2017-12-30 deposited with the CCDC.
2018-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        3-ethoxy-6-[(E)-3-pyridyliminomethyl]phenol
_chemical_name_common            5Me3SAP
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H12 N2 O'
_chemical_formula_sum            'C13 H12 N2 O'
_chemical_formula_weight         212.25

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'
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'
H H 0.0000 0.0000 '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                   14.5415(18)
_cell_length_b                   5.0163(6)
_cell_length_c                   14.8807(18)
_cell_angle_alpha                90
_cell_angle_beta                 100.551(2)
_cell_angle_gamma                90
_cell_volume                     1067.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    10577
_cell_measurement_theta_min      3.602
_cell_measurement_theta_max      27.475

_exptl_crystal_description       prizm
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.316
_exptl_crystal_size_mid          0.221
_exptl_crystal_size_min          0.216
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.821
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   'Abscor T.Higashi RIGAKU'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'RIGAKU XtaLAB mini'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 13.6612
_diffrn_reflns_number            10577
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.602
_diffrn_reflns_theta_max         27.475
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2453
_reflns_number_gt                1961
_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       'CrystalClear-SM Expert 2.0'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0'
_computing_data_reduction        'CrystalClear-SM Expert 2.0'
_computing_structure_solution    'SHELXS-97(Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
; 
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. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0594P)²+0.2196P] 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_number_reflns         2453
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1185
_refine_ls_wR_factor_gt          0.1112
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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
O1 O 0.39327(6) 0.5473(2) 0.34390(6) 0.0354(3) Uani 1 1 d . . . . .
H1 H 0.440929 0.455631 0.364069 0.053 Uiso 1 1 calc R U . . .
N1 N 0.56469(7) 0.3739(2) 0.35545(7) 0.0271(3) Uani 1 1 d . . . . .
C1 C 0.41224(8) 0.7146(2) 0.27840(8) 0.0262(3) Uani 1 1 d . . . . .
C2 C 0.34268(9) 0.8855(3) 0.23568(9) 0.0319(3) Uani 1 1 d . . . . .
H2 H 0.282749 0.882682 0.252527 0.038 Uiso 1 1 calc R U . . .
N2 N 0.76959(8) -0.0779(2) 0.37402(8) 0.0363(3) Uani 1 1 d . . . . .
C4 C 0.44701(9) 1.0710(2) 0.14194(8) 0.0268(3) Uani 1 1 d . . . . .
C3 C 0.35998(9) 1.0590(3) 0.16901(9) 0.0303(3) Uani 1 1 d . . . . .
H3 H 0.311330 1.173935 0.140580 0.036 Uiso 1 1 calc R U . . .
C6 C 0.50053(8) 0.7192(2) 0.25215(8) 0.0245(3) Uani 1 1 d . . . . .
C5 C 0.51552(8) 0.8989(3) 0.18422(8) 0.0271(3) Uani 1 1 d . . . . .
H5 H 0.575093 0.902495 0.166608 0.033 Uiso 1 1 calc R U . . .
C7 C 0.57480(9) 0.5404(3) 0.29252(8) 0.0277(3) Uani 1 1 d . . . . .
H7 H 0.632799 0.546467 0.271811 0.033 Uiso 1 1 calc R U . . .
C9 C 0.70510(9) 0.1066(3) 0.34277(9) 0.0312(3) Uani 1 1 d . . . . .
H9 H 0.706458 0.184943 0.284910 0.037 Uiso 1 1 calc R U . . .
C8 C 0.63599(8) 0.1903(3) 0.39031(8) 0.0260(3) Uani 1 1 d . . . . .
C10 C 0.76621(9) -0.1853(3) 0.45573(9) 0.0361(3) Uani 1 1 d . . . . .
H10 H 0.811672 -0.315650 0.479221 0.043 Uiso 1 1 calc R U . . .
C11 C 0.70039(10) -0.1170(3) 0.50765(9) 0.0362(3) Uani 1 1 d . . . . .
H11 H 0.700578 -0.199433 0.565163 0.043 Uiso 1 1 calc R U . . .
C12 C 0.63415(9) 0.0734(3) 0.47449(9) 0.0324(3) Uani 1 1 d . . . . .
H12 H 0.587951 0.123680 0.508878 0.039 Uiso 1 1 calc R U . . .
C13 C 0.46406(10) 1.2655(3) 0.06959(9) 0.0357(3) Uani 1 1 d . . . . .
H13A H 0.437178 1.195084 0.009044 0.054 Uiso 1 1 calc R U . . .
H13B H 0.531517 1.291424 0.073856 0.054 Uiso 1 1 calc R U . . .
H13C H 0.434566 1.436541 0.078821 0.054 Uiso 1 1 calc 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
O1 C1 1.3526(14) . ?
O1 H1 0.8400 . ?
N1 C7 1.2830(16) . ?
N1 C8 1.4127(16) . ?
C1 C2 1.3878(18) . ?
C1 C6 1.4090(16) . ?
C2 C3 1.3771(18) . ?
C2 H2 0.9500 . ?
N2 C9 1.3387(17) . ?
N2 C10 1.3389(17) . ?
C4 C5 1.3797(18) . ?
C4 C3 1.3979(18) . ?
C4 C13 1.5068(17) . ?
C3 H3 0.9500 . ?
C6 C5 1.4012(17) . ?
C6 C7 1.4471(17) . ?
C5 H5 0.9500 . ?
C7 H7 0.9500 . ?
C9 C8 1.3954(17) . ?
C9 H9 0.9500 . ?
C8 C12 1.3878(17) . ?
C10 C11 1.3787(19) . ?
C10 H10 0.9500 . ?
C11 C12 1.3821(19) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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
C1 O1 H1 109.5 . . ?
C7 N1 C8 121.19(11) . . ?
O1 C1 C2 119.05(11) . . ?
O1 C1 C6 121.75(11) . . ?
C2 C1 C6 119.19(11) . . ?
C3 C2 C1 120.41(11) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C9 N2 C10 116.98(11) . . ?
C5 C4 C3 117.24(11) . . ?
C5 C4 C13 122.10(11) . . ?
C3 C4 C13 120.66(12) . . ?
C2 C3 C4 121.96(12) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C5 C6 C1 118.72(11) . . ?
C5 C6 C7 119.70(11) . . ?
C1 C6 C7 121.57(11) . . ?
C4 C5 C6 122.46(11) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
N1 C7 C6 122.00(11) . . ?
N1 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
N2 C9 C8 123.75(12) . . ?
N2 C9 H9 118.1 . . ?
C8 C9 H9 118.1 . . ?
C12 C8 C9 117.73(12) . . ?
C12 C8 N1 118.21(11) . . ?
C9 C8 N1 123.94(11) . . ?
N2 C10 C11 123.62(13) . . ?
N2 C10 H10 118.2 . . ?
C11 C10 H10 118.2 . . ?
C10 C11 C12 118.78(12) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
C11 C12 C8 119.13(12) . . ?
C11 C12 H12 120.4 . . ?
C8 C12 H12 120.4 . . ?
C4 C13 H13A 109.5 . . ?
C4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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
_geom_hbond_publ_flag
O1 H1 N1 0.84 1.87 2.6159(14) 146.7 . yes

_refine_diff_density_max         0.176
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.043


_chemical_compound_source        non-photochromic
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1814047'
_audit_update_record             
;
2017-12-30 deposited with the CCDC.
2018-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        4-methoxy-2-[(E)-3-pyridyliminomethyl]phenol
_chemical_name_common            5OMe-3SAP
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H12 N2 O2'
_chemical_formula_sum            'C13 H12 N2 O2'
_chemical_formula_weight         228.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   6.1596(4)
_cell_length_b                   7.4634(4)
_cell_length_c                   12.7106(6)
_cell_angle_alpha                77.175(3)
_cell_angle_beta                 81.457(3)
_cell_angle_gamma                78.821(3)
_cell_volume                     555.53(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6023
_cell_measurement_theta_min      3.588
_cell_measurement_theta_max      68.211

_exptl_crystal_description       platelet
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_F_000             240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.767
_shelx_estimated_absorpt_T_min   0.900
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.721
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_process_details   abscore,T.Higashi,RIGAKU
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating anode x-ray'
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID2'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            6023
_diffrn_reflns_av_unetI/netI     0.0527
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.588
_diffrn_reflns_theta_max         68.211
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             1988
_reflns_number_gt                1318
_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       RAPID-AUTO
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        RAPID-AUTO
_computing_structure_solution    'SHELXS-97(Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
; 
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. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1209P)²] 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         1988
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.0618
_refine_ls_wR_factor_ref         0.1998
_refine_ls_wR_factor_gt          0.1638
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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 -0.1422(3) 0.7737(3) 0.89679(15) 0.0583(5) Uani 1 1 d . . . . .
C2 C -0.1364(4) 0.7433(3) 0.79332(16) 0.0668(6) Uani 1 1 d . . . . .
H2 H -0.266762 0.774051 0.759842 0.080 Uiso 1 1 calc R U . . .
C3 C 0.0579(4) 0.6684(3) 0.73818(16) 0.0627(6) Uani 1 1 d . . . . .
H3 H 0.058234 0.650085 0.668126 0.075 Uiso 1 1 calc R U . . .
C4 C 0.2527(3) 0.6205(3) 0.78770(14) 0.0571(5) Uani 1 1 d . . . . .
C5 C 0.2491(3) 0.6476(3) 0.89195(15) 0.0565(5) Uani 1 1 d . . . . .
H5 H 0.379942 0.614735 0.925049 0.068 Uiso 1 1 calc R U . . .
C6 C 0.0547(3) 0.7228(3) 0.94860(14) 0.0508(5) Uani 1 1 d . . . . .
C7 C 0.0547(3) 0.7459(3) 1.05834(14) 0.0540(5) Uani 1 1 d . . . . .
H7 H 0.186232 0.709078 1.090790 0.065 Uiso 1 1 calc R U . . .
C8 C -0.1300(3) 0.8349(3) 1.22063(14) 0.0530(5) Uani 1 1 d . . . . .
C9 C -0.3362(4) 0.9015(3) 1.26911(16) 0.0664(6) Uani 1 1 d . . . . .
H9 H -0.454951 0.930474 1.227451 0.080 Uiso 1 1 calc R U . . .
C10 C -0.2060(4) 0.8854(3) 1.42908(16) 0.0733(7) Uani 1 1 d . . . . .
H10 H -0.230265 0.901729 1.500592 0.088 Uiso 1 1 calc R U . . .
C11 C 0.0051(4) 0.8193(4) 1.38843(17) 0.0772(7) Uani 1 1 d . . . . .
H11 H 0.120999 0.792836 1.431702 0.093 Uiso 1 1 calc R U . . .
C12 C 0.0456(4) 0.7921(3) 1.28320(16) 0.0716(7) Uani 1 1 d . . . . .
H12 H 0.188201 0.745838 1.254733 0.086 Uiso 1 1 calc R U . . .
C13 C 0.4770(4) 0.5614(4) 0.62496(17) 0.0836(7) Uani 1 1 d . . . . .
H13A H 0.389926 0.481105 0.606856 0.125 Uiso 1 1 calc R U . . .
H13B H 0.630599 0.526399 0.599069 0.125 Uiso 1 1 calc R U . . .
H13C H 0.425336 0.688130 0.591592 0.125 Uiso 1 1 calc R U . . .
N1 N -0.1219(3) 0.8158(2) 1.11228(12) 0.0542(5) Uani 1 1 d . . . . .
N2 N -0.3789(3) 0.9277(3) 1.37109(14) 0.0795(6) Uani 1 1 d . . . . .
O1 O -0.3361(2) 0.8526(3) 0.94540(12) 0.0827(6) Uani 1 1 d . . . . .
H1 H -0.318801 0.860379 1.006869 0.124 Uiso 1 1 calc R U . . .
O2 O 0.4550(2) 0.5443(2) 0.73910(11) 0.0758(5) 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 O1 1.351(2) . ?
C1 C2 1.378(3) . ?
C1 C6 1.413(3) . ?
C2 C3 1.379(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(2) . ?
C4 O2 1.382(2) . ?
C5 C6 1.389(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.443(2) . ?
C7 N1 1.282(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.378(3) . ?
C8 C12 1.383(3) . ?
C8 N1 1.408(2) . ?
C9 N2 1.334(3) . ?
C9 H9 0.9300 . ?
C10 N2 1.333(3) . ?
C10 C11 1.366(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.377(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 O2 1.416(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
O1 H1 0.8200 . ?

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
O1 C1 C2 118.86(18) . . ?
O1 C1 C6 121.97(17) . . ?
C2 C1 C6 119.17(19) . . ?
C1 C2 C3 121.60(19) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C2 C3 C4 119.68(18) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 O2 116.72(18) . . ?
C5 C4 C3 119.44(19) . . ?
O2 C4 C3 123.84(17) . . ?
C4 C5 C6 121.59(18) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C1 118.51(17) . . ?
C5 C6 C7 120.42(16) . . ?
C1 C6 C7 121.07(18) . . ?
N1 C7 C6 121.74(17) . . ?
N1 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C9 C8 C12 117.05(18) . . ?
C9 C8 N1 115.98(17) . . ?
C12 C8 N1 126.96(19) . . ?
N2 C9 C8 125.1(2) . . ?
N2 C9 H9 117.4 . . ?
C8 C9 H9 117.4 . . ?
N2 C10 C11 123.10(19) . . ?
N2 C10 H10 118.5 . . ?
C11 C10 H10 118.5 . . ?
C10 C11 C12 119.8(2) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C12 C8 118.7(2) . . ?
C11 C12 H12 120.7 . . ?
C8 C12 H12 120.7 . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C7 N1 C8 123.32(16) . . ?
C10 N2 C9 116.3(2) . . ?
C1 O1 H1 109.5 . . ?
C4 O2 C13 117.15(18) . . ?

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
O1 C1 C2 C3 178.1(2) . . . . ?
C6 C1 C2 C3 -1.5(3) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C2 C3 C4 O2 179.82(17) . . . . ?
O2 C4 C5 C6 -179.83(16) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
C4 C5 C6 C7 178.66(16) . . . . ?
O1 C1 C6 C5 -178.07(18) . . . . ?
C2 C1 C6 C5 1.5(3) . . . . ?
O1 C1 C6 C7 2.7(3) . . . . ?
C2 C1 C6 C7 -177.75(17) . . . . ?
C5 C6 C7 N1 179.61(17) . . . . ?
C1 C6 C7 N1 -1.1(3) . . . . ?
C12 C8 C9 N2 0.0(4) . . . . ?
N1 C8 C9 N2 179.33(18) . . . . ?
N2 C10 C11 C12 -0.6(4) . . . . ?
C10 C11 C12 C8 0.7(4) . . . . ?
C9 C8 C12 C11 -0.4(3) . . . . ?
N1 C8 C12 C11 -179.65(18) . . . . ?
C6 C7 N1 C8 177.88(15) . . . . ?
C9 C8 N1 C7 -175.90(18) . . . . ?
C12 C8 N1 C7 3.3(3) . . . . ?
C11 C10 N2 C9 0.2(4) . . . . ?
C8 C9 N2 C10 0.1(4) . . . . ?
C5 C4 O2 C13 -163.51(18) . . . . ?
C3 C4 O2 C13 17.0(3) . . . . ?

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
O1 H1 N1 0.82 1.87 2.5978(19) 146.8 .

_refine_diff_density_max         0.240
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.103


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: diethyl ether'
_chemical_compound_source        non-photochromic
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1814060'
_audit_update_record             
;
2018-01-01 deposited with the CCDC.
2018-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        
'4-bromo-2-[(E)-3-pyridyliminomethyl]phenol/3,4-dihydroxybenzoic acid'
_chemical_name_common            5Br3SAP-3,4OHBA
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H15 Br N2 O5'
_chemical_formula_sum            'C19 H15 Br N2 O5'
_chemical_formula_weight         431.24

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'
Br Br -0.2901 2.4595 '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                   8.5222(14)
_cell_length_b                   10.8771(15)
_cell_length_c                   11.5925(19)
_cell_angle_alpha                106.506(6)
_cell_angle_beta                 103.783(4)
_cell_angle_gamma                112.254(10)
_cell_volume                     878.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4889
_cell_measurement_theta_min      3.19
_cell_measurement_theta_max      27.43

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.631
_exptl_crystal_F_000             436
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.070
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    2.375
_shelx_estimated_absorpt_T_min   0.851
_shelx_estimated_absorpt_T_max   0.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.456
_exptl_absorpt_correction_T_max  0.932
_exptl_absorpt_process_details   'Absorption was corrected by ABSCOR'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode X-ray tube'
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID IP Area Detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8609
_diffrn_reflns_av_unetI/netI     0.1082
_diffrn_reflns_av_R_equivalents  0.0758
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.184
_diffrn_reflns_theta_max         27.431
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3953
_reflns_number_gt                1664
_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       'PROCESS-AUTO (Rigaku, 1998)'
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'PROCESS-AUTO (Rigaku, 1998)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2008)'
_computing_publication_material  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0627P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3953
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1664
_refine_ls_R_factor_gt           0.0644
_refine_ls_wR_factor_ref         0.1606
_refine_ls_wR_factor_gt          0.1234
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_restrained_S_all      0.963
_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
Br1 Br 0.02659(9) 0.11731(8) -0.21639(5) 0.0826(3) Uani 1 1 d . . . . .
O1 O 0.3298(5) 0.3252(4) 0.3683(3) 0.0739(11) Uani 1 1 d . . . . .
H1 H 0.291081 0.385053 0.393985 0.111 Uiso 1 1 d R U . . .
N1 N 0.2082(6) 0.5103(5) 0.3809(4) 0.0626(12) Uani 1 1 d . . . . .
N2 N 0.2212(6) 0.7461(5) 0.6780(4) 0.0695(13) Uani 1 1 d . . . . .
C1 C 0.2618(7) 0.2805(6) 0.2362(5) 0.0620(14) Uani 1 1 d . . . . .
C2 C 0.2860(7) 0.1720(6) 0.1597(5) 0.0686(15) Uani 1 1 d . . . . .
H2 H 0.347892 0.130658 0.198627 0.082 Uiso 1 1 calc R U . . .
C3 C 0.2192(7) 0.1243(6) 0.0257(5) 0.0690(15) Uani 1 1 d . . . . .
H3 H 0.234898 0.050563 -0.025805 0.083 Uiso 1 1 calc R U . . .
C4 C 0.1283(7) 0.1872(6) -0.0314(5) 0.0619(14) Uani 1 1 d . . . . .
C5 C 0.1061(7) 0.2957(6) 0.0428(5) 0.0658(15) Uani 1 1 d . . . . .
H5 H 0.046269 0.337399 0.002669 0.079 Uiso 1 1 calc R U . . .
C6 C 0.1724(7) 0.3460(6) 0.1795(5) 0.0575(13) Uani 1 1 d . . . . .
C7 C 0.1479(7) 0.4612(6) 0.2566(5) 0.0646(15) Uani 1 1 d . . . . .
H7 H 0.086465 0.500938 0.214909 0.077 Uiso 1 1 calc R U . . .
C8 C 0.1806(7) 0.6181(6) 0.4600(5) 0.0600(14) Uani 1 1 d . . . . .
C9 C 0.2421(7) 0.6506(6) 0.5910(5) 0.0666(15) Uani 1 1 d . . . . .
H9 H 0.301904 0.602848 0.620578 0.080 Uiso 1 1 calc R U . . .
C10 C 0.1401(8) 0.8173(7) 0.6362(5) 0.0751(17) Uani 1 1 d . . . . .
H10 H 0.126284 0.885572 0.696494 0.090 Uiso 1 1 calc R U . . .
C11 C 0.0764(9) 0.7937(7) 0.5079(6) 0.0859(19) Uani 1 1 d . . . . .
H11 H 0.020193 0.845116 0.481649 0.103 Uiso 1 1 calc R U . . .
C12 C 0.0964(8) 0.6935(7) 0.4186(6) 0.0771(17) Uani 1 1 d . . . . .
H12 H 0.053963 0.676194 0.330877 0.093 Uiso 1 1 calc R U . . .
O2 O 0.6221(5) 0.6089(4) 0.3236(3) 0.0739(11) Uani 1 1 d . . . . .
H14 H 0.617779 0.542677 0.264960 0.111 Uiso 1 1 d R U . . .
O3 O 0.6077(5) 0.8369(4) 0.4906(3) 0.0800(12) Uani 1 1 d . . . . .
H15 H 0.648026 0.783716 0.507221 0.120 Uiso 1 1 d R U . . .
O4 O 0.3142(5) 0.7901(4) -0.0774(3) 0.0790(12) Uani 1 1 d . . . . .
H4 H 0.279131 0.765755 -0.156549 0.118 Uiso 1 1 d R U . . .
O5 O 0.3275(5) 0.5813(5) -0.1302(3) 0.0783(11) Uani 1 1 d . . . . .
C13 C 0.4794(7) 0.6478(6) 0.1404(5) 0.0601(14) Uani 1 1 d . . . . .
H13 H 0.478938 0.568838 0.081719 0.072 Uiso 1 1 calc R U . . .
C14 C 0.5479(7) 0.6818(6) 0.2709(5) 0.0562(13) Uani 1 1 d . . . . .
C15 C 0.5418(7) 0.7962(6) 0.3591(5) 0.0627(14) Uani 1 1 d . . . . .
C16 C 0.4686(8) 0.8749(6) 0.3128(5) 0.0709(16) Uani 1 1 d . . . . .
H16 H 0.462211 0.950286 0.370679 0.085 Uiso 1 1 calc R U . . .
C17 C 0.4050(8) 0.8418(6) 0.1809(5) 0.0704(16) Uani 1 1 d . . . . .
H17 H 0.358008 0.896265 0.150798 0.084 Uiso 1 1 calc R U . . .
C18 C 0.4105(7) 0.7287(6) 0.0934(5) 0.0565(13) Uani 1 1 d . . . . .
C19 C 0.3459(7) 0.6912(7) -0.0498(5) 0.0645(15) 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
Br1 C4 1.902(5) . ?
O1 C1 1.363(6) . ?
N1 C7 1.275(6) . ?
N1 C8 1.404(6) . ?
N2 C9 1.325(6) . ?
N2 C10 1.331(7) . ?
C1 C2 1.379(7) . ?
C1 C6 1.399(7) . ?
C2 C3 1.379(7) . ?
C3 C4 1.386(7) . ?
C4 C5 1.356(7) . ?
C5 C6 1.406(7) . ?
C6 C7 1.437(7) . ?
C8 C9 1.372(6) . ?
C8 C12 1.387(7) . ?
C10 C11 1.365(8) . ?
C11 C12 1.368(8) . ?
O2 C14 1.369(6) . ?
O3 C15 1.362(6) . ?
O4 C19 1.307(7) . ?
O5 C19 1.216(6) . ?
C13 C14 1.365(6) . ?
C13 C18 1.388(7) . ?
C14 C15 1.396(7) . ?
C15 C16 1.384(7) . ?
C16 C17 1.380(7) . ?
C17 C18 1.379(7) . ?
C18 C19 1.495(7) . ?

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
C7 N1 C8 123.8(5) . . ?
C9 N2 C10 118.1(5) . . ?
O1 C1 C2 118.9(5) . . ?
O1 C1 C6 120.5(5) . . ?
C2 C1 C6 120.6(5) . . ?
C1 C2 C3 120.4(5) . . ?
C2 C3 C4 119.4(5) . . ?
C5 C4 C3 120.8(5) . . ?
C5 C4 Br1 119.2(4) . . ?
C3 C4 Br1 119.9(4) . . ?
C4 C5 C6 120.9(5) . . ?
C1 C6 C5 117.9(5) . . ?
C1 C6 C7 121.9(5) . . ?
C5 C6 C7 120.2(5) . . ?
N1 C7 C6 121.7(5) . . ?
C9 C8 C12 117.2(5) . . ?
C9 C8 N1 116.4(5) . . ?
C12 C8 N1 126.4(5) . . ?
N2 C9 C8 123.8(5) . . ?
N2 C10 C11 122.4(5) . . ?
C10 C11 C12 119.1(6) . . ?
C11 C12 C8 119.4(5) . . ?
C14 C13 C18 121.4(5) . . ?
C13 C14 O2 124.2(5) . . ?
C13 C14 C15 119.7(5) . . ?
O2 C14 C15 116.1(4) . . ?
O3 C15 C16 117.6(5) . . ?
O3 C15 C14 123.2(5) . . ?
C16 C15 C14 119.3(5) . . ?
C17 C16 C15 120.2(5) . . ?
C18 C17 C16 120.7(5) . . ?
C17 C18 C13 118.7(5) . . ?
C17 C18 C19 122.2(5) . . ?
C13 C18 C19 119.1(5) . . ?
O5 C19 O4 124.5(5) . . ?
O5 C19 C18 123.1(6) . . ?
O4 C19 C18 112.4(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
O1 C1 C2 C3 -179.9(5) . . . . ?
C6 C1 C2 C3 -1.3(8) . . . . ?
C1 C2 C3 C4 0.4(9) . . . . ?
C2 C3 C4 C5 0.7(8) . . . . ?
C2 C3 C4 Br1 -177.5(4) . . . . ?
C3 C4 C5 C6 -0.9(8) . . . . ?
Br1 C4 C5 C6 177.3(4) . . . . ?
O1 C1 C6 C5 179.7(5) . . . . ?
C2 C1 C6 C5 1.1(8) . . . . ?
O1 C1 C6 C7 -0.2(8) . . . . ?
C2 C1 C6 C7 -178.8(5) . . . . ?
C4 C5 C6 C1 0.0(8) . . . . ?
C4 C5 C6 C7 179.9(5) . . . . ?
C8 N1 C7 C6 -177.1(5) . . . . ?
C1 C6 C7 N1 0.7(8) . . . . ?
C5 C6 C7 N1 -179.2(5) . . . . ?
C7 N1 C8 C9 175.1(5) . . . . ?
C7 N1 C8 C12 -4.4(9) . . . . ?
C10 N2 C9 C8 -1.8(9) . . . . ?
C12 C8 C9 N2 1.8(9) . . . . ?
N1 C8 C9 N2 -177.7(5) . . . . ?
C9 N2 C10 C11 0.9(9) . . . . ?
N2 C10 C11 C12 -0.1(10) . . . . ?
C10 C11 C12 C8 0.1(10) . . . . ?
C9 C8 C12 C11 -0.9(9) . . . . ?
N1 C8 C12 C11 178.6(5) . . . . ?
C18 C13 C14 O2 -178.2(5) . . . . ?
C18 C13 C14 C15 2.8(8) . . . . ?
C13 C14 C15 O3 -179.8(5) . . . . ?
O2 C14 C15 O3 1.2(8) . . . . ?
C13 C14 C15 C16 -0.9(8) . . . . ?
O2 C14 C15 C16 180.0(5) . . . . ?
O3 C15 C16 C17 177.9(5) . . . . ?
C14 C15 C16 C17 -1.0(9) . . . . ?
C15 C16 C17 C18 1.1(9) . . . . ?
C16 C17 C18 C13 0.7(9) . . . . ?
C16 C17 C18 C19 -178.9(5) . . . . ?
C14 C13 C18 C17 -2.6(8) . . . . ?
C14 C13 C18 C19 177.0(5) . . . . ?
C17 C18 C19 O5 -170.3(5) . . . . ?
C13 C18 C19 O5 10.1(8) . . . . ?
C17 C18 C19 O4 10.4(8) . . . . ?
C13 C18 C19 O4 -169.2(5) . . . . ?

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
_geom_hbond_publ_flag
O1 H1 N1 0.85 1.78 2.576(6) 155.0 . yes
C10 H10 Br1 0.93 2.95 3.810(6) 155.1 1_566 yes
C12 H12 Br1 0.93 3.12 3.746(6) 126.7 2_565 yes
O2 H14 O5 0.82 2.03 2.826(5) 165.3 2_665 yes
O3 H15 O1 0.82 2.13 2.829(5) 143.3 2_666 yes
O3 H15 O2 0.82 2.31 2.744(5) 113.3 . yes
O4 H4 N2 0.82 1.79 2.602(6) 170.0 1_554 yes

_refine_diff_density_max         0.359
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.077


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: THF'
_chemical_compound_source        non-photochromic
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1814059'
_audit_update_record             
;
2017-12-30 deposited with the CCDC.
2018-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
'4-bromo-2-[(E)-3-pyridyliminomethyl]phenol, 4-chlorobenzoic acid'
_chemical_name_common            5Br3SAP-4ClBA
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 Br N2 O, C7 H5 Cl O2'
_chemical_formula_sum            'C19 H14 Br Cl N2 O3'
_chemical_formula_weight         433.68

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'
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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   33.0322(16)
_cell_length_b                   6.2046(3)
_cell_length_c                   18.5200(8)
_cell_angle_alpha                90
_cell_angle_beta                 109.2160(10)
_cell_angle_gamma                90
_cell_volume                     3584.2(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    16181
_cell_measurement_theta_min      3.023
_cell_measurement_theta_max      27.426

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_F_000             1744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    2.465
_shelx_estimated_absorpt_T_min   0.679
_shelx_estimated_absorpt_T_max   0.809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.475
_exptl_absorpt_correction_T_max  0.801
_exptl_absorpt_process_details   abscore,T.Higashi,RIGAKU
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode x-ray'
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            16182
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.023
_diffrn_reflns_theta_max         27.426
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4063
_reflns_number_gt                2742
_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       RAPID-AUTO
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        RAPID-AUTO
_computing_structure_solution    'SHELXS-97(Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
; 
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. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0698P)²+3.5399P] 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         4063
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1468
_refine_ls_wR_factor_gt          0.1144
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_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
Br1 Br 0.70020(2) -0.09661(7) 1.00086(2) 0.0833(2) Uani 1 1 d . . . . .
Cl1 Cl 0.24621(4) 0.9867(2) 0.15265(6) 0.0900(4) Uani 1 1 d . . . . .
N1 N 0.54050(7) 0.2356(4) 0.71290(12) 0.0457(5) Uani 1 1 d . . . . .
O1 O 0.56673(8) 0.5311(4) 0.81724(13) 0.0638(6) Uani 1 1 d . . . . .
H1A H 0.551581 0.477504 0.776932 0.096 Uiso 1 1 calc R U . . .
N2 N 0.46293(8) 0.2655(4) 0.52058(13) 0.0536(6) Uani 1 1 d . . . . .
O2 O 0.41073(8) 0.5455(4) 0.42211(12) 0.0615(6) Uani 1 1 d . . . . .
H2A H 0.428727 0.460881 0.448101 0.092 Uiso 1 1 calc R U . . .
C10 C 0.44850(10) 0.0625(5) 0.50981(18) 0.0559(8) Uani 1 1 d . . . . .
H10 H 0.427744 0.027161 0.463582 0.067 Uiso 1 1 calc R U . . .
C6 C 0.59620(10) 0.3850(5) 0.85655(16) 0.0493(7) Uani 1 1 d . . . . .
C1 C 0.59889(9) 0.1789(5) 0.82775(15) 0.0445(6) Uani 1 1 d . . . . .
C7 C 0.56951(10) 0.1092(5) 0.75409(15) 0.0459(6) Uani 1 1 d . . . . .
H7 H 0.571872 -0.029393 0.736737 0.055 Uiso 1 1 calc R U . . .
C3 C 0.65757(10) 0.0977(5) 0.94195(17) 0.0559(8) Uani 1 1 d . . . . .
C13 C 0.35436(9) 0.5908(5) 0.30561(16) 0.0477(6) Uani 1 1 d . . . . .
C9 C 0.49304(9) 0.3113(5) 0.58672(16) 0.0500(7) Uani 1 1 d . . . . .
H9 H 0.503243 0.452023 0.594967 0.060 Uiso 1 1 calc R U . . .
C19 C 0.38969(11) 0.4554(5) 0.35556(17) 0.0544(7) Uani 1 1 d . . . . .
O3 O 0.39859(9) 0.2792(4) 0.33730(14) 0.0838(8) Uani 1 1 d . . . . .
C16 C 0.28828(10) 0.8322(6) 0.21131(18) 0.0584(8) Uani 1 1 d . . . . .
C14 C 0.34533(10) 0.7920(5) 0.32836(17) 0.0539(7) Uani 1 1 d . . . . .
H14 H 0.361799 0.845770 0.375809 0.065 Uiso 1 1 calc R U . . .
C15 C 0.31211(11) 0.9141(5) 0.2814(2) 0.0607(8) Uani 1 1 d . . . . .
H15 H 0.305974 1.049228 0.296840 0.073 Uiso 1 1 calc R U . . .
C8 C 0.51009(9) 0.1606(5) 0.64415(15) 0.0436(6) Uani 1 1 d . . . . .
C18 C 0.32970(11) 0.5123(6) 0.23489(18) 0.0574(7) Uani 1 1 d . . . . .
H18 H 0.335587 0.376965 0.219218 0.069 Uiso 1 1 calc R U . . .
C17 C 0.29639(11) 0.6330(6) 0.18728(18) 0.0612(8) Uani 1 1 d . . . . .
H17 H 0.279796 0.579977 0.139799 0.073 Uiso 1 1 calc R U . . .
C12 C 0.49411(10) -0.0469(5) 0.63264(17) 0.0521(7) Uani 1 1 d . . . . .
H12 H 0.504068 -0.151555 0.670290 0.062 Uiso 1 1 calc R U . . .
C4 C 0.65456(11) 0.3010(6) 0.97013(18) 0.0640(9) Uani 1 1 d . . . . .
H4 H 0.673264 0.341646 1.017769 0.077 Uiso 1 1 calc R U . . .
C2 C 0.62995(10) 0.0358(5) 0.87160(16) 0.0521(7) Uani 1 1 d . . . . .
H2 H 0.631964 -0.101822 0.853195 0.062 Uiso 1 1 calc R U . . .
C11 C 0.46291(11) -0.0953(5) 0.56374(18) 0.0564(8) Uani 1 1 d . . . . .
H11 H 0.451832 -0.234189 0.554180 0.068 Uiso 1 1 calc R U . . .
C5 C 0.62421(11) 0.4424(6) 0.92827(18) 0.0603(8) Uani 1 1 d . . . . .
H5 H 0.622233 0.578469 0.947873 0.072 Uiso 1 1 calc 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
Br1 C3 1.902(3) . ?
Cl1 C16 1.742(3) . ?
N1 C7 1.278(4) . ?
N1 C8 1.416(3) . ?
O1 C6 1.354(4) . ?
O1 H1A 0.8200 . ?
N2 C9 1.330(4) . ?
N2 C10 1.338(4) . ?
O2 C19 1.323(4) . ?
O2 H2A 0.8200 . ?
C10 C11 1.368(5) . ?
C10 H10 0.9300 . ?
C6 C5 1.392(4) . ?
C6 C1 1.400(4) . ?
C1 C2 1.397(4) . ?
C1 C7 1.456(4) . ?
C7 H7 0.9300 . ?
C3 C2 1.377(4) . ?
C3 C4 1.381(5) . ?
C13 C14 1.381(4) . ?
C13 C18 1.383(4) . ?
C13 C19 1.487(4) . ?
C9 C8 1.389(4) . ?
C9 H9 0.9300 . ?
C19 O3 1.209(4) . ?
C16 C17 1.370(5) . ?
C16 C15 1.374(5) . ?
C14 C15 1.381(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C8 C12 1.381(4) . ?
C18 C17 1.382(5) . ?
C18 H18 0.9300 . ?
C17 H17 0.9300 . ?
C12 C11 1.384(4) . ?
C12 H12 0.9300 . ?
C4 C5 1.365(5) . ?
C4 H4 0.9300 . ?
C2 H2 0.9300 . ?
C11 H11 0.9300 . ?
C5 H5 0.9300 . ?

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
C7 N1 C8 120.4(2) . . ?
C6 O1 H1A 109.5 . . ?
C9 N2 C10 117.4(3) . . ?
C19 O2 H2A 109.5 . . ?
N2 C10 C11 123.0(3) . . ?
N2 C10 H10 118.5 . . ?
C11 C10 H10 118.5 . . ?
O1 C6 C5 118.4(3) . . ?
O1 C6 C1 122.1(3) . . ?
C5 C6 C1 119.4(3) . . ?
C2 C1 C6 119.1(3) . . ?
C2 C1 C7 119.4(3) . . ?
C6 C1 C7 121.5(3) . . ?
N1 C7 C1 121.0(2) . . ?
N1 C7 H7 119.5 . . ?
C1 C7 H7 119.5 . . ?
C2 C3 C4 120.3(3) . . ?
C2 C3 Br1 120.1(3) . . ?
C4 C3 Br1 119.6(2) . . ?
C14 C13 C18 119.2(3) . . ?
C14 C13 C19 121.6(3) . . ?
C18 C13 C19 119.2(3) . . ?
N2 C9 C8 123.6(3) . . ?
N2 C9 H9 118.2 . . ?
C8 C9 H9 118.2 . . ?
O3 C19 O2 122.8(3) . . ?
O3 C19 C13 123.4(3) . . ?
O2 C19 C13 113.9(3) . . ?
C17 C16 C15 121.8(3) . . ?
C17 C16 Cl1 119.7(3) . . ?
C15 C16 Cl1 118.5(3) . . ?
C15 C14 C13 120.7(3) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 118.8(3) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C12 C8 C9 118.1(3) . . ?
C12 C8 N1 124.5(3) . . ?
C9 C8 N1 117.1(3) . . ?
C17 C18 C13 120.7(3) . . ?
C17 C18 H18 119.6 . . ?
C13 C18 H18 119.6 . . ?
C16 C17 C18 118.8(3) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
C8 C12 C11 118.4(3) . . ?
C8 C12 H12 120.8 . . ?
C11 C12 H12 120.8 . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C3 C2 C1 120.3(3) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C10 C11 C12 119.5(3) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C4 C5 C6 120.7(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?

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
C9 N2 C10 C11 0.9(5) . . . . ?
O1 C6 C1 C2 -179.7(3) . . . . ?
C5 C6 C1 C2 -0.5(4) . . . . ?
O1 C6 C1 C7 -1.0(5) . . . . ?
C5 C6 C1 C7 178.2(3) . . . . ?
C8 N1 C7 C1 -175.2(3) . . . . ?
C2 C1 C7 N1 179.4(3) . . . . ?
C6 C1 C7 N1 0.8(4) . . . . ?
C10 N2 C9 C8 0.3(5) . . . . ?
C14 C13 C19 O3 -179.6(3) . . . . ?
C18 C13 C19 O3 1.0(5) . . . . ?
C14 C13 C19 O2 0.3(4) . . . . ?
C18 C13 C19 O2 -179.2(3) . . . . ?
C18 C13 C14 C15 0.1(5) . . . . ?
C19 C13 C14 C15 -179.4(3) . . . . ?
C17 C16 C15 C14 0.5(5) . . . . ?
Cl1 C16 C15 C14 179.6(3) . . . . ?
C13 C14 C15 C16 -0.3(5) . . . . ?
N2 C9 C8 C12 -1.7(5) . . . . ?
N2 C9 C8 N1 -177.1(3) . . . . ?
C7 N1 C8 C12 33.4(4) . . . . ?
C7 N1 C8 C9 -151.5(3) . . . . ?
C14 C13 C18 C17 0.0(5) . . . . ?
C19 C13 C18 C17 179.5(3) . . . . ?
C15 C16 C17 C18 -0.4(5) . . . . ?
Cl1 C16 C17 C18 -179.5(3) . . . . ?
C13 C18 C17 C16 0.1(5) . . . . ?
C9 C8 C12 C11 1.9(4) . . . . ?
N1 C8 C12 C11 176.9(3) . . . . ?
C2 C3 C4 C5 -0.2(5) . . . . ?
Br1 C3 C4 C5 179.7(3) . . . . ?
C4 C3 C2 C1 0.7(5) . . . . ?
Br1 C3 C2 C1 -179.3(2) . . . . ?
C6 C1 C2 C3 -0.3(5) . . . . ?
C7 C1 C2 C3 -179.0(3) . . . . ?
N2 C10 C11 C12 -0.6(5) . . . . ?
C8 C12 C11 C10 -0.8(5) . . . . ?
C3 C4 C5 C6 -0.6(5) . . . . ?
O1 C6 C5 C4 -179.9(3) . . . . ?
C1 C6 C5 C4 0.9(5) . . . . ?

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
O1 H1A N1 0.82 1.87 2.597(3) 146.6 .
O2 H2A N2 0.82 1.88 2.692(3) 168.3 .
C7 H7 O3 0.93 2.47 3.310(4) 149.8 5_656
C4 H4 Cl1 0.93 2.98 3.896(3) 167.9 3_546

_refine_diff_density_max         0.387
_refine_diff_density_min         -0.797
_refine_diff_density_rms         0.115


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: THF'
_chemical_compound_source        photochromic
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 1814055'
_audit_update_record             
;
2017-12-30 deposited with the CCDC.
2018-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        
(E)-4-bromo-2-(((5-methylpyridin-3-yl)imino)methyl)phenol
_chemical_name_common            5Br-5M3SAP
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H11 Br N2 O'
_chemical_formula_sum            'C13 H11 Br N2 O'
_chemical_formula_weight         291.15

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   5.8531(9)
_cell_length_b                   7.5224(12)
_cell_length_c                   13.598(2)
_cell_angle_alpha                94.526(7)
_cell_angle_beta                 93.369(7)
_cell_angle_gamma                99.310(7)
_cell_volume                     587.41(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5510
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      27.52

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_F_000             292
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    3.482
_shelx_estimated_absorpt_T_min   0.432
_shelx_estimated_absorpt_T_max   0.641
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.331
_exptl_absorpt_correction_T_max  0.641
_exptl_absorpt_process_details   'Absorption was corrected by ABSCOR'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focued X-ray tube'
_diffrn_measurement_device_type  
'RIGAKU XtaLab mini CCD Area Detector(MercuryIII)'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6173
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.014
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2698
_reflns_number_gt                2093
_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       'PROCESS-AUTO (Rigaku, 1998)'
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'PROCESS-AUTO (Rigaku, 1998)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2008)'
_computing_publication_material  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0393P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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_number_reflns         2698
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0826
_refine_ls_wR_factor_gt          0.0766
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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
Br1 Br 0.17525(5) 0.26466(4) 0.05187(2) 0.05706(13) Uani 1 1 d . . . . .
O1 O 0.8604(3) 0.4204(3) 0.40776(13) 0.0545(5) Uani 1 1 d . . . . .
H1 H 0.804196 0.378924 0.456633 0.082 Uiso 1 1 calc R U . . .
N1 N 0.1545(4) 0.0687(3) 0.70071(17) 0.0574(6) Uani 1 1 d . . . . .
N2 N 0.5268(3) 0.2652(2) 0.51167(14) 0.0379(4) Uani 1 1 d . . . . .
C1 C 0.7016(4) 0.3836(3) 0.32996(18) 0.0384(5) Uani 1 1 d . . . . .
C2 C 0.7672(4) 0.4324(3) 0.23842(19) 0.0449(6) Uani 1 1 d . . . . .
H2 H 0.918295 0.489663 0.232415 0.054 Uiso 1 1 calc R U . . .
C3 C 0.6135(4) 0.3979(3) 0.15630(19) 0.0447(6) Uani 1 1 d . . . . .
H3 H 0.659698 0.430814 0.095074 0.054 Uiso 1 1 calc R U . . .
C4 C 0.3890(4) 0.3135(3) 0.16593(17) 0.0383(5) Uani 1 1 d . . . . .
C5 C 0.3185(4) 0.2635(3) 0.25525(17) 0.0390(5) Uani 1 1 d . . . . .
H5 H 0.166666 0.206772 0.260138 0.047 Uiso 1 1 calc R U . . .
C6 C 0.4734(4) 0.2973(3) 0.33906(17) 0.0333(5) Uani 1 1 d . . . . .
C7 C 0.3954(4) 0.2406(3) 0.43243(17) 0.0387(5) Uani 1 1 d . . . . .
H7 H 0.242565 0.183679 0.434493 0.046 Uiso 1 1 calc R U . . .
C8 C 0.4476(4) 0.2056(3) 0.60205(16) 0.0345(5) Uani 1 1 d . . . . .
C9 C 0.2215(4) 0.1290(4) 0.6159(2) 0.0533(7) Uani 1 1 d . . . . .
H9 H 0.110547 0.119189 0.563089 0.064 Uiso 1 1 calc R U . . .
C10 C 0.3128(4) 0.0887(3) 0.77614(19) 0.0463(6) Uani 1 1 d . . . . .
H10 H 0.267424 0.044950 0.835321 0.056 Uiso 1 1 calc R U . . .
C11 C 0.5419(4) 0.1705(3) 0.77274(18) 0.0396(5) Uani 1 1 d . . . . .
C12 C 0.6073(4) 0.2265(3) 0.68275(17) 0.0364(5) Uani 1 1 d . . . . .
H12 H 0.760403 0.278626 0.676388 0.044 Uiso 1 1 calc R U . . .
C13 C 0.7090(5) 0.1940(4) 0.8626(2) 0.0555(7) Uani 1 1 d . . . . .
H13A H 0.852238 0.158045 0.844834 0.083 Uiso 1 1 calc R U . . .
H13B H 0.643906 0.120453 0.911872 0.083 Uiso 1 1 calc R U . . .
H13C H 0.737709 0.318711 0.888454 0.083 Uiso 1 1 calc 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
Br1 C4 1.908(2) . ?
O1 C1 1.347(3) . ?
O1 H1 0.8200 . ?
N1 C10 1.324(3) . ?
N1 C9 1.329(3) . ?
N2 C7 1.270(3) . ?
N2 C8 1.419(3) . ?
C1 C2 1.384(3) . ?
C1 C6 1.405(3) . ?
C2 C3 1.373(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.367(3) . ?
C5 C6 1.394(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.447(3) . ?
C7 H7 0.9300 . ?
C8 C12 1.381(3) . ?
C8 C9 1.385(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.387(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.380(3) . ?
C11 C13 1.499(3) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C10 N1 C9 117.5(2) . . ?
C7 N2 C8 121.77(19) . . ?
O1 C1 C2 118.5(2) . . ?
O1 C1 C6 122.1(2) . . ?
C2 C1 C6 119.4(2) . . ?
C3 C2 C1 121.2(2) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 119.0(2) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 121.2(2) . . ?
C5 C4 Br1 119.63(18) . . ?
C3 C4 Br1 119.13(18) . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 118.9(2) . . ?
C5 C6 C7 119.1(2) . . ?
C1 C6 C7 122.0(2) . . ?
N2 C7 C6 122.8(2) . . ?
N2 C7 H7 118.6 . . ?
C6 C7 H7 118.6 . . ?
C12 C8 C9 117.3(2) . . ?
C12 C8 N2 117.68(19) . . ?
C9 C8 N2 125.0(2) . . ?
N1 C9 C8 123.6(2) . . ?
N1 C9 H9 118.2 . . ?
C8 C9 H9 118.2 . . ?
N1 C10 C11 124.3(2) . . ?
N1 C10 H10 117.8 . . ?
C11 C10 H10 117.8 . . ?
C12 C11 C10 116.6(2) . . ?
C12 C11 C13 122.2(2) . . ?
C10 C11 C13 121.1(2) . . ?
C11 C12 C8 120.6(2) . . ?
C11 C12 H12 119.7 . . ?
C8 C12 H12 119.7 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
O1 C1 C2 C3 179.7(2) . . . . ?
C6 C1 C2 C3 -0.1(4) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C2 C3 C4 Br1 -179.80(18) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
Br1 C4 C5 C6 179.57(16) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
C4 C5 C6 C7 -179.1(2) . . . . ?
O1 C1 C6 C5 -180.0(2) . . . . ?
C2 C1 C6 C5 -0.2(3) . . . . ?
O1 C1 C6 C7 -0.7(4) . . . . ?
C2 C1 C6 C7 179.0(2) . . . . ?
C8 N2 C7 C6 -178.90(19) . . . . ?
C5 C6 C7 N2 179.4(2) . . . . ?
C1 C6 C7 N2 0.2(4) . . . . ?
C7 N2 C8 C12 175.4(2) . . . . ?
C7 N2 C8 C9 -5.1(4) . . . . ?
C10 N1 C9 C8 2.0(4) . . . . ?
C12 C8 C9 N1 -2.9(4) . . . . ?
N2 C8 C9 N1 177.5(2) . . . . ?
C9 N1 C10 C11 1.0(4) . . . . ?
N1 C10 C11 C12 -3.0(4) . . . . ?
N1 C10 C11 C13 177.8(2) . . . . ?
C10 C11 C12 C8 2.0(3) . . . . ?
C13 C11 C12 C8 -178.8(2) . . . . ?
C9 C8 C12 C11 0.7(3) . . . . ?
N2 C8 C12 C11 -179.7(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
_geom_hbond_publ_flag
O1 H1 N2 0.82 1.93 2.650(3) 146.0 . yes
C5 H5 N1 0.93 2.67 3.530(3) 153.6 2_556 yes

_refine_diff_density_max         0.324
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.066


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
_chemical_compound_source        non-photochromic
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 1814054'
_audit_update_record             
;
2017-12-30 deposited with the CCDC.
2018-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        
4-chloro-6-[(E)-3-pyridylimino-5-methyl]phenol
_chemical_name_common            5Cl-5Me3SAP
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H11 Cl N2 O'
_chemical_formula_sum            'C13 H11 Cl N2 O'
_chemical_formula_weight         246.69

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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                   5.8388(13)
_cell_length_b                   7.4762(17)
_cell_length_c                   13.369(3)
_cell_angle_alpha                93.793(7)
_cell_angle_beta                 93.656(7)
_cell_angle_gamma                99.044(7)
_cell_volume                     573.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6067
_cell_measurement_theta_min      3.058
_cell_measurement_theta_max      27.482

_exptl_crystal_description       prizm
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_F_000             256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.235
_exptl_crystal_size_mid          0.235
_exptl_crystal_size_min          0.187
_exptl_absorpt_coefficient_mu    0.316
_shelx_estimated_absorpt_T_min   0.929
_shelx_estimated_absorpt_T_max   0.943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.830
_exptl_absorpt_correction_T_max  0.943
_exptl_absorpt_process_details   'Abscor T.Higashi RIGAKU'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube with SHINE monochrometor X-ray'
_diffrn_measurement_device_type  'RIGAKU XtaLAB mini'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 13.6612
_diffrn_reflns_number            6067
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_av_R_equivalents  0.0164
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.058
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2634
_reflns_number_gt                2162
_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       'CrystalClear-SM Expert 2.0'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0'
_computing_data_reduction        'CrystalClear-SM Expert 2.0'
_computing_structure_solution    'SHELXS-97(Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
; 
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. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0618P)²+0.1268P] 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_number_reflns         2634
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1196
_refine_ls_wR_factor_gt          0.1126
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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
Cl1 Cl 0.18521(8) 0.27542(7) 0.05649(3) 0.05997(19) Uani 1 1 d . . . . .
O1 O 0.8608(2) 0.41991(19) 0.40732(9) 0.0535(3) Uani 1 1 d . . . . .
H1 H 0.804919 0.378879 0.457398 0.080 Uiso 1 1 calc R U . . .
N1 N 0.5292(2) 0.26326(17) 0.51394(9) 0.0375(3) Uani 1 1 d . . . . .
N2 N 0.1575(3) 0.0665(2) 0.70734(11) 0.0568(4) Uani 1 1 d . . . . .
C1 C 0.7006(3) 0.3838(2) 0.32840(11) 0.0375(3) Uani 1 1 d . . . . .
C2 C 0.7652(3) 0.4340(2) 0.23486(12) 0.0450(4) Uani 1 1 d . . . . .
H2 H 0.916588 0.490345 0.228098 0.054 Uiso 1 1 calc R U . . .
C3 C 0.6081(3) 0.4014(2) 0.15200(12) 0.0442(4) Uani 1 1 d . . . . .
H3 H 0.652782 0.435772 0.089600 0.053 Uiso 1 1 calc R U . . .
C4 C 0.3838(3) 0.3174(2) 0.16215(11) 0.0403(3) Uani 1 1 d . . . . .
C5 C 0.3147(3) 0.2653(2) 0.25338(11) 0.0392(3) Uani 1 1 d . . . . .
H5 H 0.163090 0.208215 0.258849 0.047 Uiso 1 1 calc R U . . .
C6 C 0.4728(2) 0.29819(19) 0.33835(11) 0.0339(3) Uani 1 1 d . . . . .
C7 C 0.3956(3) 0.2401(2) 0.43338(11) 0.0377(3) Uani 1 1 d . . . . .
H7 H 0.242506 0.183723 0.435828 0.045 Uiso 1 1 calc R U . . .
C8 C 0.4506(2) 0.20297(19) 0.60603(11) 0.0342(3) Uani 1 1 d . . . . .
C9 C 0.2242(3) 0.1265(3) 0.62046(12) 0.0509(4) Uani 1 1 d . . . . .
H9 H 0.112869 0.116403 0.566560 0.061 Uiso 1 1 calc R U . . .
C10 C 0.3176(3) 0.0864(2) 0.78429(12) 0.0467(4) Uani 1 1 d . . . . .
H10 H 0.272409 0.043804 0.844995 0.056 Uiso 1 1 calc R U . . .
C11 C 0.5464(3) 0.1660(2) 0.78021(11) 0.0387(3) Uani 1 1 d . . . . .
C12 C 0.6116(3) 0.2233(2) 0.68807(11) 0.0369(3) Uani 1 1 d . . . . .
H12 H 0.764637 0.275781 0.681432 0.044 Uiso 1 1 calc R U . . .
C13 C 0.7152(3) 0.1887(3) 0.87148(13) 0.0560(5) Uani 1 1 d . . . . .
H13A H 0.643232 0.127135 0.925017 0.084 Uiso 1 1 calc R U . . .
H13B H 0.759314 0.315566 0.892094 0.084 Uiso 1 1 calc R U . . .
H13C H 0.850836 0.137902 0.855679 0.084 Uiso 1 1 calc 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
Cl1 C4 1.7482(16) . ?
O1 C1 1.3487(18) . ?
O1 H1 0.8200 . ?
N1 C7 1.2745(19) . ?
N1 C8 1.4179(19) . ?
N2 C10 1.330(2) . ?
N2 C9 1.332(2) . ?
C1 C2 1.387(2) . ?
C1 C6 1.401(2) . ?
C2 C3 1.376(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(2) . ?
C5 C6 1.400(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.446(2) . ?
C7 H7 0.9300 . ?
C8 C12 1.383(2) . ?
C8 C9 1.386(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.380(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.387(2) . ?
C11 C13 1.502(2) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C7 N1 C8 121.55(13) . . ?
C10 N2 C9 117.39(14) . . ?
O1 C1 C2 118.43(14) . . ?
O1 C1 C6 122.04(13) . . ?
C2 C1 C6 119.53(14) . . ?
C3 C2 C1 120.79(14) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 119.51(14) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 121.14(14) . . ?
C5 C4 Cl1 119.54(12) . . ?
C3 C4 Cl1 119.32(12) . . ?
C4 C5 C6 119.90(14) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 119.13(13) . . ?
C5 C6 C7 118.66(13) . . ?
C1 C6 C7 122.20(13) . . ?
N1 C7 C6 122.55(13) . . ?
N1 C7 H7 118.7 . . ?
C6 C7 H7 118.7 . . ?
C12 C8 C9 117.39(14) . . ?
C12 C8 N1 117.53(13) . . ?
C9 C8 N1 125.07(13) . . ?
N2 C9 C8 123.52(15) . . ?
N2 C9 H9 118.2 . . ?
C8 C9 H9 118.2 . . ?
N2 C10 C11 124.46(15) . . ?
N2 C10 H10 117.8 . . ?
C11 C10 H10 117.8 . . ?
C10 C11 C12 116.73(14) . . ?
C10 C11 C13 121.24(15) . . ?
C12 C11 C13 122.03(15) . . ?
C8 C12 C11 120.45(14) . . ?
C8 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
O1 C1 C2 C3 -179.58(14) . . . . ?
C6 C1 C2 C3 0.3(2) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C2 C3 C4 Cl1 -179.72(12) . . . . ?
C3 C4 C5 C6 0.4(2) . . . . ?
Cl1 C4 C5 C6 179.91(11) . . . . ?
C4 C5 C6 C1 -0.2(2) . . . . ?
C4 C5 C6 C7 -179.40(14) . . . . ?
O1 C1 C6 C5 179.77(14) . . . . ?
C2 C1 C6 C5 -0.1(2) . . . . ?
O1 C1 C6 C7 -1.1(2) . . . . ?
C2 C1 C6 C7 179.04(14) . . . . ?
C8 N1 C7 C6 -179.14(13) . . . . ?
C5 C6 C7 N1 179.26(14) . . . . ?
C1 C6 C7 N1 0.1(2) . . . . ?
C7 N1 C8 C12 175.92(13) . . . . ?
C7 N1 C8 C9 -4.6(2) . . . . ?
C10 N2 C9 C8 1.7(3) . . . . ?
C12 C8 C9 N2 -2.5(3) . . . . ?
N1 C8 C9 N2 178.05(16) . . . . ?
C9 N2 C10 C11 0.6(3) . . . . ?
N2 C10 C11 C12 -2.0(3) . . . . ?
N2 C10 C11 C13 178.03(16) . . . . ?
C9 C8 C12 C11 0.9(2) . . . . ?
N1 C8 C12 C11 -179.54(13) . . . . ?
C10 C11 C12 C8 1.1(2) . . . . ?
C13 C11 C12 C8 -178.90(14) . . . . ?

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
_geom_hbond_publ_flag
O1 H1 N1 0.82 1.93 2.6480(17) 146.2 . yes
C5 H5 N2 0.93 2.64 3.498(2) 154.5 2_556 yes

_refine_diff_density_max         0.168
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.063


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
_chemical_compound_source        non-photochromic
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC6
_database_code_depnum_ccdc_archive 'CCDC 1814057'
_audit_update_record             
;
2017-12-30 deposited with the CCDC.
2018-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
'4-bromo-2-[(E)-3-pyridyliminomethyl]phenol/benzoic acid'
_chemical_name_common            5Br3SAP-BA
_chemical_melting_point          ?
_chemical_formula_moiety         '(C12 H9 Br N2 O), (C7 H6 O2)'
_chemical_formula_sum            'C19 H15 Br N2 O3'
_chemical_formula_weight         399.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   32.6081(14)
_cell_length_b                   6.1424(3)
_cell_length_c                   17.8481(8)
_cell_angle_alpha                90
_cell_angle_beta                 106.922(3)
_cell_angle_gamma                90
_cell_volume                     3420.0(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    18693
_cell_measurement_theta_min      5.131
_cell_measurement_theta_max      68.264

_exptl_crystal_description       prizm
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_F_000             1616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.196
_exptl_crystal_size_mid          0.176
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    3.456
_shelx_estimated_absorpt_T_min   0.551
_shelx_estimated_absorpt_T_max   0.903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.687
_exptl_absorpt_correction_T_max  0.903
_exptl_absorpt_process_details   abscore,T.Higashi,RIGAKU
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_type           CuK\a
_diffrn_source                   RIGAKU
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            18693
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         5.131
_diffrn_reflns_theta_max         68.264
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3128
_reflns_number_gt                2402
_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       RAPID-AUTO
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        RAPID-AUTO
_computing_structure_solution    'SHELXS-97(Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0589P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3128
_refine_ls_number_parameters     232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1145
_refine_ls_wR_factor_gt          0.1075
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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
Br1 Br 0.70740(2) 1.06329(6) 0.98772(2) 0.05949(18) Uani 1 1 d . . . . .
N1 N 0.54087(6) 0.7480(3) 0.71171(11) 0.0298(5) Uani 1 1 d . . . . .
H1 H 0.5746(8) 1.023(4) 0.7356(14) 0.032(7) Uiso 1 1 d . . . . .
O1 O 0.56738(6) 0.4475(3) 0.81740(11) 0.0399(5) Uani 1 1 d . . . . .
H1A H 0.553413 0.499513 0.773940 0.060 Uiso 1 1 calc R U . . .
C1 C 0.59780(9) 0.5911(4) 0.85504(15) 0.0330(6) Uani 1 1 d . . . . .
C3 C 0.65882(9) 0.6701(5) 0.96515(15) 0.0425(7) Uani 1 1 d . . . . .
H3 H 0.678752 0.627038 1.013159 0.051 Uiso 1 1 calc R U . . .
O3 O 0.40900(6) 0.4430(3) 0.42235(10) 0.0384(5) Uani 1 1 d . . . . .
H3A H 0.426331 0.532371 0.450301 0.058 Uiso 1 1 calc R U . . .
O2 O 0.39487(7) 0.7203(3) 0.33768(11) 0.0548(6) Uani 1 1 d . . . . .
N2 N 0.46193(7) 0.7234(3) 0.51909(12) 0.0348(5) Uani 1 1 d . . . . .
C2 C 0.62705(9) 0.5294(5) 0.92587(16) 0.0398(7) Uani 1 1 d . . . . .
H2 H 0.624975 0.389337 0.947042 0.048 Uiso 1 1 calc R U . . .
C18 C 0.30691(10) 0.0818(5) 0.28827(19) 0.0511(8) Uani 1 1 d . . . . .
H18 H 0.300707 -0.057420 0.305440 0.061 Uiso 1 1 calc R U . . .
C17 C 0.28242(10) 0.1632(6) 0.21826(19) 0.0579(9) Uani 1 1 d . . . . .
H17 H 0.259311 0.079510 0.186683 0.069 Uiso 1 1 calc R U . . .
C16 C 0.29105(9) 0.3671(6) 0.19291(17) 0.0540(8) Uani 1 1 d . . . . .
H16 H 0.273909 0.422682 0.144164 0.065 Uiso 1 1 calc R U . . .
C19 C 0.34088(8) 0.2034(4) 0.33425(16) 0.0417(7) Uani 1 1 d . . . . .
H19 H 0.357968 0.146732 0.382838 0.050 Uiso 1 1 calc R U . . .
C15 C 0.32443(9) 0.4883(5) 0.23849(16) 0.0434(7) Uani 1 1 d . . . . .
H15 H 0.330109 0.628552 0.221378 0.052 Uiso 1 1 calc R U . . .
C14 C 0.35001(8) 0.4073(4) 0.30962(15) 0.0338(6) Uani 1 1 d . . . . .
C13 C 0.38639(9) 0.5403(4) 0.35706(15) 0.0366(6) Uani 1 1 d . . . . .
C12 C 0.49413(8) 1.0370(4) 0.63371(15) 0.0328(6) Uani 1 1 d . . . . .
H12 H 0.504788 1.144054 0.672976 0.039 Uiso 1 1 calc R U . . .
C11 C 0.46265(9) 1.0877(4) 0.56561(15) 0.0344(6) Uani 1 1 d . . . . .
H11 H 0.451334 1.231198 0.557406 0.041 Uiso 1 1 calc R U . . .
C10 C 0.44767(9) 0.9298(4) 0.50954(15) 0.0354(6) Uani 1 1 d . . . . .
H10 H 0.426479 0.968193 0.462388 0.043 Uiso 1 1 calc R U . . .
C9 C 0.49251(8) 0.6735(4) 0.58467(14) 0.0328(6) Uani 1 1 d . . . . .
H9 H 0.502916 0.528149 0.591606 0.039 Uiso 1 1 calc R U . . .
C8 C 0.50990(7) 0.8250(4) 0.64349(13) 0.0282(5) Uani 1 1 d . . . . .
C7 C 0.57065(8) 0.8744(4) 0.75138(14) 0.0309(6) Uani 1 1 d . . . . .
C6 C 0.60066(8) 0.8009(4) 0.82449(13) 0.0297(5) Uani 1 1 d . . . . .
C5 C 0.63333(9) 0.9406(4) 0.86543(16) 0.0358(6) Uani 1 1 d . . . . .
H5 H 0.635873 1.081502 0.845283 0.043 Uiso 1 1 calc R U . . .
C4 C 0.66173(9) 0.8749(5) 0.93457(15) 0.0408(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
Br1 C4 1.906(3) . ?
N1 C7 1.283(3) . ?
N1 C8 1.418(3) . ?
O1 C1 1.351(3) . ?
O1 H1A 0.8400 . ?
C1 C2 1.396(4) . ?
C1 C6 1.413(3) . ?
C3 C2 1.375(4) . ?
C3 C4 1.385(4) . ?
C3 H3 0.9500 . ?
O3 C13 1.326(3) . ?
O3 H3A 0.8400 . ?
O2 C13 1.214(3) . ?
N2 C9 1.334(3) . ?
N2 C10 1.345(3) . ?
C2 H2 0.9500 . ?
C18 C17 1.367(4) . ?
C18 C19 1.389(4) . ?
C18 H18 0.9500 . ?
C17 C16 1.388(5) . ?
C17 H17 0.9500 . ?
C16 C15 1.373(4) . ?
C16 H16 0.9500 . ?
C19 C14 1.388(3) . ?
C19 H19 0.9500 . ?
C15 C14 1.392(4) . ?
C15 H15 0.9500 . ?
C14 C13 1.486(4) . ?
C12 C11 1.379(3) . ?
C12 C8 1.392(3) . ?
C12 H12 0.9500 . ?
C11 C10 1.377(3) . ?
C11 H11 0.9500 . ?
C10 H10 0.9500 . ?
C9 C8 1.394(3) . ?
C9 H9 0.9500 . ?
C7 C6 1.456(3) . ?
C7 H1 0.97(3) . ?
C6 C5 1.397(3) . ?
C5 C4 1.370(4) . ?
C5 H5 0.9500 . ?

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
C7 N1 C8 120.5(2) . . ?
C1 O1 H1A 109.5 . . ?
O1 C1 C2 118.8(2) . . ?
O1 C1 C6 121.7(2) . . ?
C2 C1 C6 119.5(2) . . ?
C2 C3 C4 119.9(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C13 O3 H3A 109.5 . . ?
C9 N2 C10 118.1(2) . . ?
C3 C2 C1 120.4(2) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C17 C18 C19 119.8(3) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C18 C17 C16 120.5(3) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C15 C16 C17 119.8(3) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C14 C19 C18 120.4(3) . . ?
C14 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C16 C15 C14 120.5(3) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C19 C14 C15 119.0(3) . . ?
C19 C14 C13 121.7(2) . . ?
C15 C14 C13 119.3(2) . . ?
O2 C13 O3 123.1(3) . . ?
O2 C13 C14 123.3(2) . . ?
O3 C13 C14 113.6(2) . . ?
C11 C12 C8 118.4(2) . . ?
C11 C12 H12 120.8 . . ?
C8 C12 H12 120.8 . . ?
C10 C11 C12 119.8(2) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
N2 C10 C11 122.4(2) . . ?
N2 C10 H10 118.8 . . ?
C11 C10 H10 118.8 . . ?
N2 C9 C8 122.9(2) . . ?
N2 C9 H9 118.5 . . ?
C8 C9 H9 118.5 . . ?
C12 C8 C9 118.4(2) . . ?
C12 C8 N1 124.4(2) . . ?
C9 C8 N1 117.1(2) . . ?
N1 C7 C6 120.7(2) . . ?
N1 C7 H1 123.4(15) . . ?
C6 C7 H1 115.9(15) . . ?
C5 C6 C1 119.0(2) . . ?
C5 C6 C7 119.3(2) . . ?
C1 C6 C7 121.7(2) . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C4 C3 121.1(3) . . ?
C5 C4 Br1 119.6(2) . . ?
C3 C4 Br1 119.2(2) . . ?

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
C4 C3 C2 C1 0.4(4) . . . . ?
O1 C1 C2 C3 179.0(2) . . . . ?
C6 C1 C2 C3 -1.0(4) . . . . ?
C19 C18 C17 C16 -0.4(5) . . . . ?
C18 C17 C16 C15 0.0(5) . . . . ?
C17 C18 C19 C14 0.2(4) . . . . ?
C17 C16 C15 C14 0.7(4) . . . . ?
C18 C19 C14 C15 0.5(4) . . . . ?
C18 C19 C14 C13 -179.4(3) . . . . ?
C16 C15 C14 C19 -0.9(4) . . . . ?
C16 C15 C14 C13 178.9(2) . . . . ?
C19 C14 C13 O2 -179.0(3) . . . . ?
C15 C14 C13 O2 1.2(4) . . . . ?
C19 C14 C13 O3 1.6(4) . . . . ?
C15 C14 C13 O3 -178.2(2) . . . . ?
C8 C12 C11 C10 0.1(4) . . . . ?
C9 N2 C10 C11 -1.8(4) . . . . ?
C12 C11 C10 N2 1.5(4) . . . . ?
C10 N2 C9 C8 0.5(4) . . . . ?
C11 C12 C8 C9 -1.2(4) . . . . ?
C11 C12 C8 N1 -177.2(2) . . . . ?
N2 C9 C8 C12 1.0(4) . . . . ?
N2 C9 C8 N1 177.3(2) . . . . ?
C7 N1 C8 C12 -33.9(3) . . . . ?
C7 N1 C8 C9 150.1(2) . . . . ?
C8 N1 C7 C6 175.6(2) . . . . ?
O1 C1 C6 C5 -178.8(2) . . . . ?
C2 C1 C6 C5 1.2(4) . . . . ?
O1 C1 C6 C7 0.8(4) . . . . ?
C2 C1 C6 C7 -179.2(2) . . . . ?
N1 C7 C6 C5 178.6(2) . . . . ?
N1 C7 C6 C1 -1.0(4) . . . . ?
C1 C6 C5 C4 -0.8(4) . . . . ?
C7 C6 C5 C4 179.6(2) . . . . ?
C6 C5 C4 C3 0.2(4) . . . . ?
C6 C5 C4 Br1 177.68(18) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C2 C3 C4 Br1 -177.5(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
C7 H1 O2 0.97(3) 2.44(2) 3.321(3) 150.5(19) 5_676
O1 H1A N1 0.84 1.86 2.600(2) 146.0 .
O3 H3A N2 0.84 1.84 2.682(3) 174.5 .
C10 H10 O2 0.95 2.65 3.310(3) 127.4 .

_refine_diff_density_max         0.718
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.076


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
_chemical_compound_source        photochromic
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC7
_database_code_depnum_ccdc_archive 'CCDC 1814053'
_audit_update_record             
;
2017-12-30 deposited with the CCDC.
2018-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
(E)-2-(tert-butyl)-6-(((5-methylpyridin-3-yl)imino)methyl)phenol
_chemical_name_common            3Me-5MSAP
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H20 N2 O'
_chemical_formula_sum            'C17 H20 N2 O'
_chemical_formula_weight         268.35

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.0801(5)
_cell_length_b                   15.1860(13)
_cell_length_c                   16.4018(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1514.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    13932
_cell_measurement_theta_min      3.58
_cell_measurement_theta_max      27.61

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.335
_exptl_crystal_size_mid          0.234
_exptl_crystal_size_min          0.187
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.793
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'Absorption was corrected by ABSCOR'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focued X-ray tube'
_diffrn_measurement_device_type  
'RIGAKU XtaLab mini CCD Area Detector(MercuryIII)'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16034
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.574
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3465
_reflns_number_gt                2919
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       'PROCESS-AUTO (Rigaku, 1998)'
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'PROCESS-AUTO (Rigaku, 1998)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2008)'
_computing_publication_material  'SHELXL-2014/07 (Sheldrick, 2014)'
_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)+(0.0703P)²+0.0891P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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 x determined using 1025 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(7)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3465
_refine_ls_number_parameters     186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.1221
_refine_ls_wR_factor_gt          0.1150
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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
O1 O 0.7301(3) 0.40729(9) 0.54642(10) 0.0479(4) Uani 1 1 d . . . . .
H1 H 0.628049 0.433960 0.524994 0.072 Uiso 1 1 calc R U . . .
N1 N 0.4827(3) 0.53745(11) 0.50455(11) 0.0389(4) Uani 1 1 d . . . . .
N2 N 0.0440(4) 0.68421(13) 0.42579(14) 0.0552(6) Uani 1 1 d . . . . .
C1 C 0.8475(3) 0.46302(13) 0.59272(12) 0.0348(4) Uani 1 1 d . . . . .
C2 C 1.0260(4) 0.43106(13) 0.63862(12) 0.0367(5) Uani 1 1 d . . . . .
C3 C 1.1467(4) 0.49301(17) 0.68186(14) 0.0466(6) Uani 1 1 d . . . . .
H3 H 1.267280 0.473917 0.711929 0.056 Uiso 1 1 calc R U . . .
C4 C 1.0959(4) 0.58218(17) 0.68232(15) 0.0521(6) Uani 1 1 d . . . . .
H4 H 1.183416 0.621596 0.711140 0.063 Uiso 1 1 calc R U . . .
C5 C 0.9170(4) 0.61157(14) 0.64025(14) 0.0465(6) Uani 1 1 d . . . . .
H5 H 0.879777 0.670938 0.642027 0.056 Uiso 1 1 calc R U . . .
C6 C 0.7890(3) 0.55327(13) 0.59448(12) 0.0358(5) Uani 1 1 d . . . . .
C7 C 0.6004(4) 0.58631(14) 0.55055(13) 0.0401(5) Uani 1 1 d . . . . .
H7 H 0.563212 0.645428 0.555948 0.048 Uiso 1 1 calc R U . . .
C8 C 0.2956(4) 0.56961(13) 0.46303(12) 0.0368(5) Uani 1 1 d . . . . .
C9 C 0.2245(4) 0.65658(15) 0.46375(15) 0.0489(6) Uani 1 1 d . . . . .
H9 H 0.307615 0.697683 0.492323 0.059 Uiso 1 1 calc R U . . .
C10 C -0.0723(4) 0.62416(17) 0.38499(15) 0.0503(6) Uani 1 1 d . . . . .
H10 H -0.199909 0.642805 0.358940 0.060 Uiso 1 1 calc R U . . .
C11 C -0.0165(4) 0.53623(15) 0.37869(13) 0.0446(5) Uani 1 1 d . . . . .
C12 C 0.1720(4) 0.51008(14) 0.41864(13) 0.0413(5) Uani 1 1 d . . . . .
H12 H 0.216718 0.451599 0.415676 0.050 Uiso 1 1 calc R U . . .
C13 C 1.0868(4) 0.33281(15) 0.63941(14) 0.0438(5) Uani 1 1 d . . . . .
C14 C 1.2723(6) 0.3138(2) 0.70029(19) 0.0740(9) Uani 1 1 d . . . . .
H14A H 1.400700 0.346826 0.685344 0.111 Uiso 1 1 calc R U . . .
H14B H 1.306101 0.252027 0.699548 0.111 Uiso 1 1 calc R U . . .
H14C H 1.226173 0.330548 0.754065 0.111 Uiso 1 1 calc R U . . .
C15 C 1.1646(4) 0.30490(16) 0.55473(15) 0.0529(6) Uani 1 1 d . . . . .
H15A H 1.051293 0.317046 0.515538 0.079 Uiso 1 1 calc R U . . .
H15B H 1.196363 0.242975 0.554783 0.079 Uiso 1 1 calc R U . . .
H15C H 1.294978 0.337125 0.540632 0.079 Uiso 1 1 calc R U . . .
C16 C 0.8881(5) 0.27591(17) 0.66399(18) 0.0605(7) Uani 1 1 d . . . . .
H16A H 0.841181 0.291797 0.717909 0.091 Uiso 1 1 calc R U . . .
H16B H 0.929246 0.214891 0.663141 0.091 Uiso 1 1 calc R U . . .
H16C H 0.769809 0.285559 0.626246 0.091 Uiso 1 1 calc R U . . .
C17 C -0.1571(5) 0.4730(2) 0.33131(18) 0.0691(8) Uani 1 1 d . . . . .
H17A H -0.141551 0.414952 0.353665 0.104 Uiso 1 1 calc R U . . .
H17B H -0.111503 0.472789 0.275282 0.104 Uiso 1 1 calc R U . . .
H17C H -0.308260 0.490995 0.334708 0.104 Uiso 1 1 calc 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
O1 C1 1.343(2) . ?
O1 H1 0.8200 . ?
N1 C7 1.278(3) . ?
N1 C8 1.413(3) . ?
N2 C9 1.330(3) . ?
N2 C10 1.334(3) . ?
C1 C2 1.407(3) . ?
C1 C6 1.416(3) . ?
C2 C3 1.388(3) . ?
C2 C13 1.537(3) . ?
C3 C4 1.389(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.363(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.398(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.444(3) . ?
C7 H7 0.9300 . ?
C8 C12 1.383(3) . ?
C8 C9 1.390(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.381(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.379(3) . ?
C11 C17 1.502(4) . ?
C12 H12 0.9300 . ?
C13 C15 1.527(3) . ?
C13 C14 1.534(4) . ?
C13 C16 1.539(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C7 N1 C8 122.34(17) . . ?
C9 N2 C10 117.2(2) . . ?
O1 C1 C2 119.69(17) . . ?
O1 C1 C6 119.20(18) . . ?
C2 C1 C6 121.11(18) . . ?
C3 C2 C1 116.57(19) . . ?
C3 C2 C13 121.76(19) . . ?
C1 C2 C13 121.65(18) . . ?
C2 C3 C4 123.1(2) . . ?
C2 C3 H3 118.5 . . ?
C4 C3 H3 118.5 . . ?
C5 C4 C3 119.6(2) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 120.6(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 118.95(19) . . ?
C5 C6 C7 119.34(18) . . ?
C1 C6 C7 121.70(18) . . ?
N1 C7 C6 122.52(18) . . ?
N1 C7 H7 118.7 . . ?
C6 C7 H7 118.7 . . ?
C12 C8 C9 117.2(2) . . ?
C12 C8 N1 117.73(18) . . ?
C9 C8 N1 125.1(2) . . ?
N2 C9 C8 123.6(2) . . ?
N2 C9 H9 118.2 . . ?
C8 C9 H9 118.2 . . ?
N2 C10 C11 124.6(2) . . ?
N2 C10 H10 117.7 . . ?
C11 C10 H10 117.7 . . ?
C12 C11 C10 116.5(2) . . ?
C12 C11 C17 122.4(2) . . ?
C10 C11 C17 121.1(2) . . ?
C11 C12 C8 120.9(2) . . ?
C11 C12 H12 119.5 . . ?
C8 C12 H12 119.5 . . ?
C15 C13 C14 108.2(2) . . ?
C15 C13 C2 109.65(19) . . ?
C14 C13 C2 111.4(2) . . ?
C15 C13 C16 109.0(2) . . ?
C14 C13 C16 107.5(2) . . ?
C2 C13 C16 110.99(19) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 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 . . ?
C11 C17 H17A 109.5 . . ?
C11 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C11 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
O1 H1 N1 0.82 1.83 2.577(2) 150.0 .
C7 H7 N2 0.93 2.61 3.523(3) 168.5 4_566
C9 H9 N2 0.93 2.66 3.592(3) 179.7 4_566

_refine_diff_density_max         0.183
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.057


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
_chemical_compound_source        non-photochromic
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC8
_database_code_depnum_ccdc_archive 'CCDC 1814061'
_audit_update_record             
;
2017-12-30 deposited with the CCDC.
2018-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
'4-bromo-2-[(E)-3-pyridyliminomethyl]phenol, 3,5-dihydroxybenzoic acid'
_chemical_name_common            5Br3SAP-35OHBA
_chemical_melting_point          ?
_chemical_formula_moiety         '3(C12 H9 Br N2 O), 2(C7 H6 O4)'
_chemical_formula_sum            'C50 H39 Br3 N6 O11'
_chemical_formula_weight         1139.60

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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'

_cell_length_a                   8.2123(2)
_cell_length_b                   12.3360(2)
_cell_length_c                   13.0008(2)
_cell_angle_alpha                65.6550(10)
_cell_angle_beta                 78.6480(10)
_cell_angle_gamma                83.5680(10)
_cell_volume                     1175.78(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    13821
_cell_measurement_theta_min      3.785
_cell_measurement_theta_max      68.250

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_F_000             574
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    3.768
_shelx_estimated_absorpt_T_min   0.704
_shelx_estimated_absorpt_T_max   0.864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.733
_exptl_absorpt_correction_T_max  0.860
_exptl_absorpt_process_details   abscore,T.Higashi,RIGAKU
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating anode x-ray'
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID2'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            13821
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.785
_diffrn_reflns_theta_max         68.250
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.841
_diffrn_reflns_point_group_measured_fraction_full 0.843
_reflns_number_total             7248
_reflns_number_gt                5499
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_max     0.698
_reflns_Friedel_fraction_full    0.702

_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       RAPID-AUTO
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        RAPID-AUTO
_computing_structure_solution    'SIR2004(Burla et al., 2004)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
; 
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. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0469P)²+0.9386P] 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_abs_structure_details 
; 
 Flack x determined using 1758 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.015(8)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         7248
_refine_ls_number_parameters     640
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.1303
_refine_ls_wR_factor_gt          0.1011
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_restrained_S_all      1.123
_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
Br1 Br 0.55325(15) 1.26578(11) 0.25090(11) 0.0900(4) Uani 1 1 d . . . . .
Br2 Br 0.6114(2) 0.18164(14) 0.91589(13) 0.1312(7) Uani 1 1 d . . . . .
Br3 Br 0.00446(13) 1.00417(10) -0.00360(9) 0.0815(4) Uani 1 1 d . . . . .
O1 O 0.8975(9) 0.7868(7) 0.4530(6) 0.084(2) Uani 1 1 d . . . . .
H1A H 0.850904 0.747956 0.518138 0.127 Uiso 1 1 calc R U . . .
O2 O 0.1174(9) 0.5512(7) 0.6752(7) 0.084(2) Uani 1 1 d . . . . .
H2A H 0.160929 0.593818 0.610463 0.126 Uiso 1 1 calc R U . . .
O3 O 0.4505(8) 0.5698(6) 0.1755(6) 0.076(2) Uani 1 1 d . . . . .
H3A H 0.408827 0.523454 0.239224 0.113 Uiso 1 1 calc R U . . .
O4 O 1.1881(8) 0.9130(7) 0.5972(5) 0.077(2) Uani 1 1 d . . . . .
H4A H 1.184981 0.962354 0.531843 0.116 Uiso 1 1 calc R U . . .
O5 O 0.8383(9) 0.7579(6) 0.9602(5) 0.075(2) Uani 1 1 d . . . . .
H5A H 0.908980 0.703741 0.970209 0.112 Uiso 1 1 calc R U . . .
O6 O 0.6735(8) 1.1965(5) 0.5718(6) 0.0682(19) Uani 1 1 d . . . . .
O7 O 0.4916(8) 1.0698(6) 0.7067(6) 0.081(2) Uani 1 1 d . . . . .
H7A H 0.423820 1.119693 0.673836 0.122 Uiso 1 1 calc R U . . .
O8 O 0.0609(8) 0.5669(5) 0.0097(5) 0.0630(18) Uani 1 1 d . . . . .
H8A H 0.157292 0.559861 -0.019569 0.095 Uiso 1 1 calc R U . . .
O9 O -0.2627(8) 0.4170(6) 0.3801(6) 0.0629(18) Uani 1 1 d . . . . .
H9A H -0.278778 0.354719 0.437223 0.094 Uiso 1 1 calc R U . . .
O10 O 0.2438(8) 0.1346(5) 0.1922(5) 0.0577(16) Uani 1 1 d . . . . .
H10A H 0.284432 0.066681 0.214831 0.086 Uiso 1 1 calc R U . . .
O11 O 0.1750(8) 0.0907(5) 0.3797(5) 0.0659(18) Uani 1 1 d . . . . .
N1 N 0.6766(9) 0.7387(7) 0.6355(7) 0.0575(19) Uani 1 1 d . . . . .
N2 N 0.3853(9) 0.5695(6) 0.8976(6) 0.0550(18) Uani 1 1 d . . . . .
N3 N 0.3639(9) 0.6421(6) 0.5051(6) 0.0511(17) Uani 1 1 d . . . . .
N4 N 0.3975(10) 0.9243(7) 0.2558(7) 0.061(2) Uani 1 1 d . . . . .
N5 N 0.2326(8) 0.4937(6) 0.3627(6) 0.0495(17) Uani 1 1 d . . . . .
N6 N 0.2660(9) 0.2259(7) 0.6163(7) 0.063(2) Uani 1 1 d . . . . .
C1 C 0.8152(12) 0.8937(9) 0.4091(8) 0.064(3) Uani 1 1 d . . . . .
C2 C 0.8765(14) 0.9765(10) 0.3021(9) 0.079(3) Uani 1 1 d . . . . .
H2 H 0.973449 0.958291 0.260732 0.095 Uiso 1 1 calc R U . . .
C3 C 0.7973(15) 1.0849(10) 0.2557(9) 0.074(3) Uani 1 1 d . . . . .
H3 H 0.839774 1.139395 0.183090 0.089 Uiso 1 1 calc R U . . .
C4 C 0.6560(13) 1.1131(9) 0.3161(9) 0.067(3) Uani 1 1 d . . . . .
C5 C 0.5916(12) 1.0327(9) 0.4236(9) 0.065(3) Uani 1 1 d . . . . .
H5 H 0.494744 1.052888 0.463607 0.078 Uiso 1 1 calc R U . . .
C6 C 0.6693(11) 0.9225(8) 0.4727(7) 0.055(2) Uani 1 1 d . . . . .
C7 C 0.6074(12) 0.8418(9) 0.5878(8) 0.059(2) Uani 1 1 d . . . . .
H7 H 0.514576 0.864979 0.628867 0.071 Uiso 1 1 calc R U . . .
C8 C 0.6115(11) 0.6598(8) 0.7503(8) 0.052(2) Uani 1 1 d . . . . .
C9 C 0.4458(10) 0.6476(8) 0.7932(8) 0.054(2) Uani 1 1 d . . . . .
H9 H 0.370853 0.696523 0.747115 0.064 Uiso 1 1 calc R U . . .
C10 C 0.4953(12) 0.5031(9) 0.9605(9) 0.067(3) Uani 1 1 d . . . . .
H10 H 0.455485 0.448629 1.033818 0.080 Uiso 1 1 calc R U . . .
C11 C 0.6655(12) 0.5081(10) 0.9260(9) 0.073(3) Uani 1 1 d . . . . .
H11 H 0.737333 0.459181 0.974657 0.088 Uiso 1 1 calc R U . . .
C12 C 0.7256(12) 0.5881(10) 0.8171(9) 0.070(3) Uani 1 1 d . . . . .
H12 H 0.839139 0.593669 0.789440 0.085 Uiso 1 1 calc R U . . .
C13 C 0.2257(13) 0.4667(9) 0.7247(8) 0.066(3) Uani 1 1 d . . . . .
C14 C 0.1797(15) 0.3756(10) 0.8326(9) 0.076(3) Uani 1 1 d . . . . .
H14 H 0.069214 0.372570 0.867865 0.091 Uiso 1 1 calc R U . . .
C15 C 0.2903(16) 0.2913(9) 0.8879(9) 0.076(3) Uani 1 1 d . . . . .
H15 H 0.255071 0.231887 0.959450 0.091 Uiso 1 1 calc R U . . .
C16 C 0.4527(16) 0.2945(9) 0.8380(9) 0.078(3) Uani 1 1 d . . . . .
C17 C 0.5074(14) 0.3796(9) 0.7314(8) 0.073(3) Uani 1 1 d . . . . .
H17 H 0.618386 0.379137 0.697919 0.087 Uiso 1 1 calc R U . . .
C18 C 0.3964(12) 0.4661(8) 0.6740(8) 0.056(2) Uani 1 1 d . . . . .
C19 C 0.4565(12) 0.5576(8) 0.5626(7) 0.055(2) Uani 1 1 d . . . . .
H19 H 0.568220 0.554366 0.531636 0.066 Uiso 1 1 calc R U . . .
C20 C 0.4284(10) 0.7260(7) 0.3956(7) 0.047(2) Uani 1 1 d . . . . .
C21 C 0.5613(11) 0.7023(8) 0.3221(8) 0.057(2) Uani 1 1 d . . . . .
H21 H 0.615912 0.628081 0.343468 0.068 Uiso 1 1 calc R U . . .
C22 C 0.6096(12) 0.7930(8) 0.2162(8) 0.063(3) Uani 1 1 d . . . . .
H22 H 0.697707 0.780052 0.164936 0.076 Uiso 1 1 calc R U . . .
C23 C 0.5276(12) 0.9014(8) 0.1871(9) 0.064(3) Uani 1 1 d . . . . .
H23 H 0.563828 0.961748 0.116457 0.077 Uiso 1 1 calc R U . . .
C24 C 0.3486(12) 0.8372(8) 0.3571(8) 0.057(2) Uani 1 1 d . . . . .
H24 H 0.256096 0.851672 0.404484 0.068 Uiso 1 1 calc R U . . .
C25 C 0.3482(12) 0.6650(8) 0.1381(8) 0.058(2) Uani 1 1 d . . . . .
C26 C 0.3913(12) 0.7534(8) 0.0279(9) 0.065(3) Uani 1 1 d . . . . .
H26 H 0.489983 0.744575 -0.017712 0.079 Uiso 1 1 calc R U . . .
C27 C 0.2907(13) 0.8526(9) -0.0136(9) 0.068(3) Uani 1 1 d . . . . .
H27 H 0.321063 0.910282 -0.087012 0.081 Uiso 1 1 calc R U . . .
C28 C 0.1438(12) 0.8669(8) 0.0535(8) 0.058(2) Uani 1 1 d . . . . .
C29 C 0.0961(11) 0.7795(8) 0.1604(8) 0.057(2) Uani 1 1 d . . . . .
H29 H -0.005238 0.788471 0.203435 0.069 Uiso 1 1 calc R U . . .
C30 C 0.1953(10) 0.6786(7) 0.2054(7) 0.049(2) Uani 1 1 d . . . . .
C31 C 0.1439(11) 0.5874(8) 0.3191(8) 0.054(2) Uani 1 1 d . . . . .
H31 H 0.042684 0.597943 0.361416 0.065 Uiso 1 1 calc R U . . .
C32 C 0.1804(10) 0.4048(7) 0.4719(7) 0.050(2) Uani 1 1 d . . . . .
C33 C 0.2960(11) 0.3174(8) 0.5151(8) 0.063(3) Uani 1 1 d . . . . .
H33 H 0.401423 0.321979 0.471636 0.076 Uiso 1 1 calc R U . . .
C34 C 0.1157(12) 0.2164(9) 0.6751(8) 0.064(3) Uani 1 1 d . . . . .
H34 H 0.092980 0.151350 0.744648 0.077 Uiso 1 1 calc R U . . .
C35 C -0.0094(12) 0.2983(11) 0.6382(9) 0.082(3) Uani 1 1 d . . . . .
H35 H -0.114542 0.289713 0.682754 0.098 Uiso 1 1 calc R U . . .
C36 C 0.0220(12) 0.3935(10) 0.5347(9) 0.076(3) Uani 1 1 d . . . . .
H36 H -0.061892 0.449408 0.507317 0.091 Uiso 1 1 calc R U . . .
C37 C 0.7731(10) 1.0082(7) 0.6980(8) 0.051(2) Uani 1 1 d . . . . .
C38 C 0.7435(11) 0.9240(8) 0.8101(8) 0.056(2) Uani 1 1 d . . . . .
H38 H 0.643350 0.924986 0.857847 0.067 Uiso 1 1 calc R U . . .
C39 C 0.8672(11) 0.8383(8) 0.8491(7) 0.053(2) Uani 1 1 d . . . . .
C40 C 1.0148(10) 0.8357(8) 0.7778(8) 0.057(2) Uani 1 1 d . . . . .
H40 H 1.096334 0.777733 0.805423 0.069 Uiso 1 1 calc R U . . .
C41 C 1.0429(11) 0.9184(8) 0.6654(7) 0.053(2) Uani 1 1 d . . . . .
C42 C 0.9216(10) 1.0072(8) 0.6252(8) 0.054(2) Uani 1 1 d . . . . .
H42 H 0.939971 1.064831 0.550708 0.065 Uiso 1 1 calc R U . . .
C43 C 0.6427(11) 1.1020(8) 0.6525(8) 0.054(2) Uani 1 1 d . . . . .
C44 C 0.0795(9) 0.2766(7) 0.2481(7) 0.0433(19) Uani 1 1 d . . . . .
C45 C 0.1153(10) 0.3661(7) 0.1408(6) 0.0437(19) Uani 1 1 d . . . . .
H45 H 0.198660 0.354455 0.086117 0.052 Uiso 1 1 calc R U . . .
C46 C 0.0266(10) 0.4732(7) 0.1148(7) 0.045(2) Uani 1 1 d . . . . .
C47 C -0.1013(10) 0.4904(7) 0.1944(7) 0.048(2) Uani 1 1 d . . . . .
H47 H -0.163061 0.561835 0.175926 0.058 Uiso 1 1 calc R U . . .
C48 C -0.1356(10) 0.3991(7) 0.3019(7) 0.044(2) Uani 1 1 d . . . . .
C49 C -0.0434(10) 0.2925(7) 0.3300(7) 0.049(2) Uani 1 1 d . . . . .
H49 H -0.064377 0.232668 0.403136 0.058 Uiso 1 1 calc R U . . .
C50 C 0.1717(11) 0.1584(7) 0.2806(7) 0.051(2) 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
Br1 C4 1.894(12) . ?
Br2 C16 1.900(12) . ?
Br3 C28 1.895(10) . ?
O1 C1 1.362(12) . ?
O1 H1A 0.8200 . ?
O2 C13 1.325(12) . ?
O2 H2A 0.8200 . ?
O3 C25 1.338(10) . ?
O3 H3A 0.8200 . ?
O4 C41 1.352(10) . ?
O4 H4A 0.8200 . ?
O5 C39 1.365(10) . ?
O5 H5A 0.8200 . ?
O6 C43 1.215(10) . ?
O7 C43 1.315(10) . ?
O7 H7A 0.8200 . ?
O8 C46 1.378(9) . ?
O8 H8A 0.8200 . ?
O9 C48 1.375(9) . ?
O9 H9A 0.8200 . ?
O10 C50 1.315(10) . ?
O10 H10A 0.8200 . ?
O11 C50 1.217(9) . ?
N1 C7 1.285(11) . ?
N1 C8 1.437(11) . ?
N2 C10 1.315(12) . ?
N2 C9 1.335(10) . ?
N3 C19 1.276(10) . ?
N3 C20 1.410(10) . ?
N4 C24 1.331(11) . ?
N4 C23 1.335(11) . ?
N5 C31 1.274(11) . ?
N5 C32 1.408(10) . ?
N6 C34 1.307(11) . ?
N6 C33 1.333(11) . ?
C1 C2 1.378(13) . ?
C1 C6 1.414(13) . ?
C2 C3 1.368(16) . ?
C2 H2 0.9300 . ?
C3 C4 1.363(14) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(13) . ?
C5 C6 1.383(13) . ?
C5 H5 0.9300 . ?
C6 C7 1.440(12) . ?
C7 H7 0.9300 . ?
C8 C9 1.366(11) . ?
C8 C12 1.384(12) . ?
C9 H9 0.9300 . ?
C10 C11 1.382(13) . ?
C10 H10 0.9300 . ?
C11 C12 1.380(13) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.400(13) . ?
C13 C18 1.428(13) . ?
C14 C15 1.361(15) . ?
C14 H14 0.9300 . ?
C15 C16 1.361(15) . ?
C15 H15 0.9300 . ?
C16 C17 1.373(13) . ?
C17 C18 1.386(13) . ?
C17 H17 0.9300 . ?
C18 C19 1.453(12) . ?
C19 H19 0.9300 . ?
C20 C24 1.387(11) . ?
C20 C21 1.391(11) . ?
C21 C22 1.385(12) . ?
C21 H21 0.9300 . ?
C22 C23 1.366(12) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C26 1.402(13) . ?
C25 C30 1.418(12) . ?
C26 C27 1.370(13) . ?
C26 H26 0.9300 . ?
C27 C28 1.383(13) . ?
C27 H27 0.9300 . ?
C28 C29 1.375(12) . ?
C29 C30 1.385(12) . ?
C29 H29 0.9300 . ?
C30 C31 1.456(12) . ?
C31 H31 0.9300 . ?
C32 C33 1.364(12) . ?
C32 C36 1.380(12) . ?
C33 H33 0.9300 . ?
C34 C35 1.367(13) . ?
C34 H34 0.9300 . ?
C35 C36 1.373(13) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C37 C38 1.390(11) . ?
C37 C42 1.391(11) . ?
C37 C43 1.498(11) . ?
C38 C39 1.388(12) . ?
C38 H38 0.9300 . ?
C39 C40 1.379(11) . ?
C40 C41 1.385(12) . ?
C40 H40 0.9300 . ?
C41 C42 1.398(12) . ?
C42 H42 0.9300 . ?
C44 C45 1.376(10) . ?
C44 C49 1.377(10) . ?
C44 C50 1.499(11) . ?
C45 C46 1.380(10) . ?
C45 H45 0.9300 . ?
C46 C47 1.386(10) . ?
C47 C48 1.386(11) . ?
C47 H47 0.9300 . ?
C48 C49 1.387(11) . ?
C49 H49 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1A 109.5 . . ?
C13 O2 H2A 109.5 . . ?
C25 O3 H3A 109.5 . . ?
C41 O4 H4A 109.5 . . ?
C39 O5 H5A 109.5 . . ?
C43 O7 H7A 109.5 . . ?
C46 O8 H8A 109.5 . . ?
C48 O9 H9A 109.5 . . ?
C50 O10 H10A 109.5 . . ?
C7 N1 C8 120.7(8) . . ?
C10 N2 C9 116.3(8) . . ?
C19 N3 C20 120.7(7) . . ?
C24 N4 C23 117.7(8) . . ?
C31 N5 C32 121.9(8) . . ?
C34 N6 C33 118.3(8) . . ?
O1 C1 C2 119.6(9) . . ?
O1 C1 C6 121.1(8) . . ?
C2 C1 C6 119.3(10) . . ?
C3 C2 C1 121.2(10) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C4 C3 C2 120.0(10) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.5(11) . . ?
C3 C4 Br1 118.8(8) . . ?
C5 C4 Br1 120.8(9) . . ?
C4 C5 C6 120.8(10) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 118.3(8) . . ?
C5 C6 C7 120.6(9) . . ?
C1 C6 C7 121.0(9) . . ?
N1 C7 C6 122.0(9) . . ?
N1 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
C9 C8 C12 119.4(9) . . ?
C9 C8 N1 123.7(8) . . ?
C12 C8 N1 116.8(8) . . ?
N2 C9 C8 123.6(9) . . ?
N2 C9 H9 118.2 . . ?
C8 C9 H9 118.2 . . ?
N2 C10 C11 124.9(9) . . ?
N2 C10 H10 117.5 . . ?
C11 C10 H10 117.5 . . ?
C12 C11 C10 117.9(10) . . ?
C12 C11 H11 121.0 . . ?
C10 C11 H11 121.0 . . ?
C11 C12 C8 117.8(9) . . ?
C11 C12 H12 121.1 . . ?
C8 C12 H12 121.1 . . ?
O2 C13 C14 121.4(10) . . ?
O2 C13 C18 122.3(9) . . ?
C14 C13 C18 116.2(10) . . ?
C15 C14 C13 122.6(11) . . ?
C15 C14 H14 118.7 . . ?
C13 C14 H14 118.7 . . ?
C16 C15 C14 119.6(10) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 121.4(11) . . ?
C15 C16 Br2 120.5(8) . . ?
C17 C16 Br2 118.1(9) . . ?
C16 C17 C18 119.7(10) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C17 C18 C13 120.4(9) . . ?
C17 C18 C19 119.2(9) . . ?
C13 C18 C19 120.4(9) . . ?
N3 C19 C18 123.4(9) . . ?
N3 C19 H19 118.3 . . ?
C18 C19 H19 118.3 . . ?
C24 C20 C21 118.2(8) . . ?
C24 C20 N3 117.5(7) . . ?
C21 C20 N3 124.2(7) . . ?
C22 C21 C20 117.9(8) . . ?
C22 C21 H21 121.1 . . ?
C20 C21 H21 121.1 . . ?
C23 C22 C21 119.9(8) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
N4 C23 C22 122.8(9) . . ?
N4 C23 H23 118.6 . . ?
C22 C23 H23 118.6 . . ?
N4 C24 C20 123.4(8) . . ?
N4 C24 H24 118.3 . . ?
C20 C24 H24 118.3 . . ?
O3 C25 C26 119.2(8) . . ?
O3 C25 C30 122.2(8) . . ?
C26 C25 C30 118.6(9) . . ?
C27 C26 C25 121.2(9) . . ?
C27 C26 H26 119.4 . . ?
C25 C26 H26 119.4 . . ?
C26 C27 C28 120.0(9) . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C29 C28 C27 119.9(9) . . ?
C29 C28 Br3 120.0(7) . . ?
C27 C28 Br3 120.1(7) . . ?
C28 C29 C30 121.6(9) . . ?
C28 C29 H29 119.2 . . ?
C30 C29 H29 119.2 . . ?
C29 C30 C25 118.7(8) . . ?
C29 C30 C31 120.9(8) . . ?
C25 C30 C31 120.4(8) . . ?
N5 C31 C30 122.3(8) . . ?
N5 C31 H31 118.8 . . ?
C30 C31 H31 118.8 . . ?
C33 C32 C36 117.5(8) . . ?
C33 C32 N5 115.9(8) . . ?
C36 C32 N5 126.4(8) . . ?
N6 C33 C32 123.6(8) . . ?
N6 C33 H33 118.2 . . ?
C32 C33 H33 118.2 . . ?
N6 C34 C35 122.5(9) . . ?
N6 C34 H34 118.7 . . ?
C35 C34 H34 118.7 . . ?
C34 C35 C36 119.2(9) . . ?
C34 C35 H35 120.4 . . ?
C36 C35 H35 120.4 . . ?
C35 C36 C32 118.9(9) . . ?
C35 C36 H36 120.6 . . ?
C32 C36 H36 120.6 . . ?
C38 C37 C42 121.5(8) . . ?
C38 C37 C43 120.0(7) . . ?
C42 C37 C43 118.4(8) . . ?
C39 C38 C37 118.3(8) . . ?
C39 C38 H38 120.8 . . ?
C37 C38 H38 120.8 . . ?
O5 C39 C40 121.4(8) . . ?
O5 C39 C38 117.7(8) . . ?
C40 C39 C38 120.8(8) . . ?
C39 C40 C41 120.8(8) . . ?
C39 C40 H40 119.6 . . ?
C41 C40 H40 119.6 . . ?
O4 C41 C40 119.5(8) . . ?
O4 C41 C42 121.2(7) . . ?
C40 C41 C42 119.4(7) . . ?
C37 C42 C41 119.1(8) . . ?
C37 C42 H42 120.4 . . ?
C41 C42 H42 120.4 . . ?
O6 C43 O7 123.8(8) . . ?
O6 C43 C37 123.3(8) . . ?
O7 C43 C37 112.9(7) . . ?
C45 C44 C49 120.9(7) . . ?
C45 C44 C50 121.7(7) . . ?
C49 C44 C50 117.4(7) . . ?
C44 C45 C46 119.6(7) . . ?
C44 C45 H45 120.2 . . ?
C46 C45 H45 120.2 . . ?
O8 C46 C45 121.8(7) . . ?
O8 C46 C47 117.4(7) . . ?
C45 C46 C47 120.8(7) . . ?
C48 C47 C46 118.8(7) . . ?
C48 C47 H47 120.6 . . ?
C46 C47 H47 120.6 . . ?
O9 C48 C47 118.3(7) . . ?
O9 C48 C49 120.9(7) . . ?
C47 C48 C49 120.8(7) . . ?
C44 C49 C48 119.2(7) . . ?
C44 C49 H49 120.4 . . ?
C48 C49 H49 120.4 . . ?
O11 C50 O10 123.9(8) . . ?
O11 C50 C44 122.6(8) . . ?
O10 C50 C44 113.6(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
O1 C1 C2 C3 -179.7(10) . . . . ?
C6 C1 C2 C3 -1.1(16) . . . . ?
C1 C2 C3 C4 0.7(17) . . . . ?
C2 C3 C4 C5 -0.3(16) . . . . ?
C2 C3 C4 Br1 178.2(8) . . . . ?
C3 C4 C5 C6 0.4(15) . . . . ?
Br1 C4 C5 C6 -178.0(7) . . . . ?
C4 C5 C6 C1 -0.9(14) . . . . ?
C4 C5 C6 C7 176.1(9) . . . . ?
O1 C1 C6 C5 179.8(9) . . . . ?
C2 C1 C6 C5 1.2(14) . . . . ?
O1 C1 C6 C7 2.8(15) . . . . ?
C2 C1 C6 C7 -175.8(9) . . . . ?
C8 N1 C7 C6 -179.7(8) . . . . ?
C5 C6 C7 N1 179.7(9) . . . . ?
C1 C6 C7 N1 -3.3(15) . . . . ?
C7 N1 C8 C9 38.3(14) . . . . ?
C7 N1 C8 C12 -145.6(10) . . . . ?
C10 N2 C9 C8 0.8(13) . . . . ?
C12 C8 C9 N2 0.0(14) . . . . ?
N1 C8 C9 N2 176.0(8) . . . . ?
C9 N2 C10 C11 -0.6(15) . . . . ?
N2 C10 C11 C12 -0.4(18) . . . . ?
C10 C11 C12 C8 1.3(16) . . . . ?
C9 C8 C12 C11 -1.1(15) . . . . ?
N1 C8 C12 C11 -177.4(10) . . . . ?
O2 C13 C14 C15 -176.5(11) . . . . ?
C18 C13 C14 C15 0.8(16) . . . . ?
C13 C14 C15 C16 0.3(18) . . . . ?
C14 C15 C16 C17 -1.5(18) . . . . ?
C14 C15 C16 Br2 177.5(9) . . . . ?
C15 C16 C17 C18 1.6(18) . . . . ?
Br2 C16 C17 C18 -177.5(8) . . . . ?
C16 C17 C18 C13 -0.4(16) . . . . ?
C16 C17 C18 C19 178.4(10) . . . . ?
O2 C13 C18 C17 176.6(10) . . . . ?
C14 C13 C18 C17 -0.7(15) . . . . ?
O2 C13 C18 C19 -2.1(15) . . . . ?
C14 C13 C18 C19 -179.5(9) . . . . ?
C20 N3 C19 C18 -177.8(8) . . . . ?
C17 C18 C19 N3 -178.3(9) . . . . ?
C13 C18 C19 N3 0.5(15) . . . . ?
C19 N3 C20 C24 -155.3(9) . . . . ?
C19 N3 C20 C21 27.9(13) . . . . ?
C24 C20 C21 C22 2.2(14) . . . . ?
N3 C20 C21 C22 179.0(9) . . . . ?
C20 C21 C22 C23 0.2(15) . . . . ?
C24 N4 C23 C22 0.8(15) . . . . ?
C21 C22 C23 N4 -1.8(17) . . . . ?
C23 N4 C24 C20 1.9(15) . . . . ?
C21 C20 C24 N4 -3.4(15) . . . . ?
N3 C20 C24 N4 179.6(9) . . . . ?
O3 C25 C26 C27 -179.7(9) . . . . ?
C30 C25 C26 C27 1.5(15) . . . . ?
C25 C26 C27 C28 0.2(16) . . . . ?
C26 C27 C28 C29 -2.4(15) . . . . ?
C26 C27 C28 Br3 179.9(8) . . . . ?
C27 C28 C29 C30 2.8(15) . . . . ?
Br3 C28 C29 C30 -179.4(7) . . . . ?
C28 C29 C30 C25 -1.1(14) . . . . ?
C28 C29 C30 C31 179.4(9) . . . . ?
O3 C25 C30 C29 -179.8(9) . . . . ?
C26 C25 C30 C29 -1.1(14) . . . . ?
O3 C25 C30 C31 -0.2(14) . . . . ?
C26 C25 C30 C31 178.5(9) . . . . ?
C32 N5 C31 C30 -178.7(8) . . . . ?
C29 C30 C31 N5 -179.9(9) . . . . ?
C25 C30 C31 N5 0.5(14) . . . . ?
C31 N5 C32 C33 -171.2(9) . . . . ?
C31 N5 C32 C36 13.6(15) . . . . ?
C34 N6 C33 C32 3.2(16) . . . . ?
C36 C32 C33 N6 -3.3(16) . . . . ?
N5 C32 C33 N6 -178.9(9) . . . . ?
C33 N6 C34 C35 -2.1(16) . . . . ?
N6 C34 C35 C36 1.2(19) . . . . ?
C34 C35 C36 C32 -1.3(18) . . . . ?
C33 C32 C36 C35 2.3(16) . . . . ?
N5 C32 C36 C35 177.4(10) . . . . ?
C42 C37 C38 C39 0.6(15) . . . . ?
C43 C37 C38 C39 179.9(9) . . . . ?
C37 C38 C39 O5 178.4(9) . . . . ?
C37 C38 C39 C40 -1.0(15) . . . . ?
O5 C39 C40 C41 -179.5(9) . . . . ?
C38 C39 C40 C41 -0.1(15) . . . . ?
C39 C40 C41 O4 -179.4(9) . . . . ?
C39 C40 C41 C42 1.6(15) . . . . ?
C38 C37 C42 C41 0.8(14) . . . . ?
C43 C37 C42 C41 -178.4(8) . . . . ?
O4 C41 C42 C37 179.1(9) . . . . ?
C40 C41 C42 C37 -2.0(14) . . . . ?
C38 C37 C43 O6 157.2(10) . . . . ?
C42 C37 C43 O6 -23.6(14) . . . . ?
C38 C37 C43 O7 -24.8(13) . . . . ?
C42 C37 C43 O7 154.5(9) . . . . ?
C49 C44 C45 C46 -0.1(13) . . . . ?
C50 C44 C45 C46 179.8(8) . . . . ?
C44 C45 C46 O8 178.1(8) . . . . ?
C44 C45 C46 C47 -2.0(13) . . . . ?
O8 C46 C47 C48 -178.2(8) . . . . ?
C45 C46 C47 C48 1.9(13) . . . . ?
C46 C47 C48 O9 180.0(8) . . . . ?
C46 C47 C48 C49 0.3(13) . . . . ?
C45 C44 C49 C48 2.2(13) . . . . ?
C50 C44 C49 C48 -177.7(8) . . . . ?
O9 C48 C49 C44 178.0(8) . . . . ?
C47 C48 C49 C44 -2.3(13) . . . . ?
C45 C44 C50 O11 160.1(9) . . . . ?
C49 C44 C50 O11 -20.0(13) . . . . ?
C45 C44 C50 O10 -21.6(12) . . . . ?
C49 C44 C50 O10 158.3(8) . . . . ?

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
O1 H1A N1 0.82 1.85 2.581(9) 147.7 .
O2 H2A N3 0.82 1.91 2.636(10) 146.5 .
O3 H3A N5 0.82 1.88 2.605(9) 147.3 .
O4 H4A O11 0.82 1.97 2.787(9) 175.4 1_665
O5 H5A O8 0.82 1.93 2.750(8) 173.7 1_656
O7 H7A N6 0.82 1.77 2.592(10) 174.3 1_565
O8 H8A N2 0.82 1.96 2.771(9) 171.3 1_554
O9 H9A O6 0.82 2.03 2.846(9) 175.9 1_445
O10 H10A N4 0.82 1.81 2.629(9) 173.2 1_545
C10 H10 Br1 0.93 2.99 3.786(10) 144.6 1_546
C12 H12 O2 0.93 2.60 3.462(12) 155.2 1_655
C21 H21 O9 0.93 2.57 3.486(10) 170.1 1_655
C23 H23 Br2 0.93 2.88 3.793(10) 166.1 1_564
C34 H34 Br3 0.93 3.00 3.893(10) 161.5 1_546
C42 H42 O11 0.93 2.58 3.276(10) 132.4 1_665

_refine_diff_density_max         0.575
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.061


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methyl acetate'
_chemical_compound_source        photochromic
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC9
_database_code_depnum_ccdc_archive 'CCDC 1814062'
_audit_update_record             
;
2018-03-13 deposited with the CCDC.
2018-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        
'4-bromo-2-[(E)-3-pyridyliminomethyl]phenol, 3,5-chrolobenzoic acid'
_chemical_name_common            '5Br3SAP-35OHBA '
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H13 Br Cl2 N2 O3'
_chemical_formula_sum            'C19 H13 Br Cl2 N2 O3'
_chemical_formula_weight         468.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   34.7332(18)
_cell_length_b                   3.8928(2)
_cell_length_c                   28.2337(15)
_cell_angle_alpha                90
_cell_angle_beta                 99.982(2)
_cell_angle_gamma                90
_cell_volume                     3759.7(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3612
_cell_measurement_theta_min      5.59
_cell_measurement_theta_max      66.65

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.654
_exptl_crystal_F_000             1872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    5.799
_shelx_estimated_absorpt_T_min   0.497
_shelx_estimated_absorpt_T_max   0.893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.578
_exptl_absorpt_correction_T_max  0.893
_exptl_absorpt_process_details   'Absorption was corrected by ABSCOR'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating anode X-ray tube'
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID-II IP Area Detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19294
_diffrn_reflns_av_unetI/netI     0.0818
_diffrn_reflns_av_R_equivalents  0.1032
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         7.281
_diffrn_reflns_theta_max         67.491
_diffrn_reflns_theta_full        67.491
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3386
_reflns_number_gt                1749
_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       'PROCESS-AUTO (Rigaku, 1998)'
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'PROCESS-AUTO (Rigaku, 1998)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2008)'
_computing_publication_material  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.1330P)²+2.3188P] 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_number_reflns         3386
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1411
_refine_ls_R_factor_gt           0.0982
_refine_ls_wR_factor_ref         0.2972
_refine_ls_wR_factor_gt          0.2357
_refine_ls_goodness_of_fit_ref   1.194
_refine_ls_restrained_S_all      1.194
_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 0.0723(2) 0.154(2) 0.6516(3) 0.071(2) Uani 1 1 d . . . . .
C2 C 0.0400(3) 0.002(2) 0.6666(3) 0.076(2) Uani 1 1 d . . . . .
H2 H 0.042207 -0.091571 0.697300 0.091 Uiso 1 1 calc R U . . .
C3 C 0.0050(3) -0.007(2) 0.6356(3) 0.075(2) Uani 1 1 d . . . . .
H3 H -0.016520 -0.109980 0.645276 0.090 Uiso 1 1 calc R U . . .
C4 C 0.0014(2) 0.1341(19) 0.5903(3) 0.068(2) Uani 1 1 d . . . . .
C5 C 0.0330(2) 0.2851(19) 0.5747(3) 0.0618(18) Uani 1 1 d . . . . .
H5 H 0.030511 0.377458 0.543954 0.074 Uiso 1 1 calc R U . . .
C6 C 0.0689(2) 0.297(2) 0.6061(2) 0.0626(19) Uani 1 1 d . . . . .
C7 C 0.1021(2) 0.462(2) 0.5908(3) 0.0631(19) Uani 1 1 d . . . . .
H7 H 0.098992 0.557793 0.560168 0.076 Uiso 1 1 calc R U . . .
C8 C 0.1677(2) 0.6481(19) 0.6032(3) 0.0620(19) Uani 1 1 d . . . . .
C9 C 0.1707(2) 0.710(2) 0.5558(3) 0.0660(19) Uani 1 1 d . . . . .
H9 H 0.150506 0.640609 0.531564 0.079 Uiso 1 1 calc R U . . .
C10 C 0.2313(2) 0.963(2) 0.5785(3) 0.068(2) Uani 1 1 d . . . . .
H10 H 0.252949 1.072221 0.570066 0.082 Uiso 1 1 calc R U . . .
C11 C 0.2304(2) 0.906(2) 0.6261(3) 0.074(2) Uani 1 1 d . . . . .
H11 H 0.250981 0.976642 0.649680 0.089 Uiso 1 1 calc R U . . .
C12 C 0.1984(2) 0.742(2) 0.6386(3) 0.071(2) Uani 1 1 d . . . . .
H12 H 0.197527 0.695341 0.670684 0.086 Uiso 1 1 calc R U . . .
C13 C 0.1129(2) 1.3494(19) 0.3644(3) 0.0618(19) Uani 1 1 d . . . . .
H13 H 0.095641 1.419774 0.384261 0.074 Uiso 1 1 calc R U . . .
C14 C 0.1036(2) 1.3927(18) 0.3153(3) 0.0599(18) Uani 1 1 d . . . . .
C15 C 0.1289(2) 1.303(2) 0.2848(3) 0.0655(19) Uani 1 1 d . . . . .
H15 H 0.122385 1.337447 0.251816 0.079 Uiso 1 1 calc R U . . .
C16 C 0.1642(2) 1.159(2) 0.3052(3) 0.066(2) Uani 1 1 d . . . . .
C17 C 0.1747(2) 1.1074(18) 0.3547(2) 0.0570(18) Uani 1 1 d . . . . .
H17 H 0.198868 1.013107 0.367560 0.068 Uiso 1 1 calc R U . . .
C18 C 0.1485(2) 1.199(2) 0.3841(2) 0.0582(17) Uani 1 1 d . . . . .
C19 C 0.1580(2) 1.148(2) 0.4371(3) 0.066(2) Uani 1 1 d . . . . .
N1 N 0.13549(18) 0.4792(18) 0.6182(2) 0.0665(16) Uani 1 1 d . . . . .
N2 N 0.20211(17) 0.8675(17) 0.5436(2) 0.0693(18) Uani 1 1 d . . . . .
O1 O 0.10622(16) 0.1567(17) 0.68380(19) 0.0831(17) Uani 1 1 d . . . . .
H1A H 0.123559 0.243440 0.671407 0.125 Uiso 1 1 calc R U . . .
O2 O 0.13614(15) 1.2274(17) 0.46431(18) 0.0817(17) Uani 1 1 d . . . . .
O3 O 0.19256(14) 1.0016(18) 0.45153(18) 0.0782(16) Uani 1 1 d . . . . .
H3A H 0.195764 0.968396 0.480631 0.117 Uiso 1 1 calc R U . . .
Cl1 Cl 0.05825(6) 1.5644(6) 0.29090(7) 0.0808(7) Uani 1 1 d . . . . .
Cl2 Cl 0.19749(7) 1.0388(7) 0.26875(7) 0.0893(8) Uani 1 1 d . . . . .
Br1 Br -0.04781(3) 0.1122(3) 0.54874(4) 0.0927(5) 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 O1 1.359(9) . ?
C1 C6 1.385(10) . ?
C1 C2 1.399(11) . ?
C2 C3 1.368(11) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(10) . ?
C4 Br1 1.899(8) . ?
C5 C6 1.398(10) . ?
C5 H5 0.9300 . ?
C6 C7 1.449(10) . ?
C7 N1 1.281(9) . ?
C7 H7 0.9300 . ?
C8 C12 1.380(10) . ?
C8 C9 1.382(10) . ?
C8 N1 1.423(9) . ?
C9 N2 1.347(9) . ?
C9 H9 0.9300 . ?
C10 N2 1.337(9) . ?
C10 C11 1.369(11) . ?
C10 H10 0.9300 . ?
C11 C12 1.379(11) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.378(9) . ?
C13 C18 1.394(10) . ?
C13 H13 0.9300 . ?
C14 C15 1.378(10) . ?
C14 Cl1 1.739(8) . ?
C15 C16 1.381(10) . ?
C15 H15 0.9300 . ?
C16 C17 1.394(10) . ?
C16 Cl2 1.740(8) . ?
C17 C18 1.380(10) . ?
C17 H17 0.9300 . ?
C18 C19 1.491(10) . ?
C19 O2 1.210(8) . ?
C19 O3 1.327(8) . ?
O1 H1A 0.8200 . ?
O3 H3A 0.8200 . ?

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
O1 C1 C6 122.9(7) . . ?
O1 C1 C2 116.6(7) . . ?
C6 C1 C2 120.5(8) . . ?
C3 C2 C1 119.1(8) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 120.8(8) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 120.9(8) . . ?
C3 C4 Br1 118.9(6) . . ?
C5 C4 Br1 120.2(6) . . ?
C4 C5 C6 118.8(7) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C1 C6 C5 119.8(7) . . ?
C1 C6 C7 120.7(7) . . ?
C5 C6 C7 119.5(7) . . ?
N1 C7 C6 121.8(7) . . ?
N1 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C12 C8 C9 118.5(7) . . ?
C12 C8 N1 117.1(7) . . ?
C9 C8 N1 124.4(7) . . ?
N2 C9 C8 121.8(7) . . ?
N2 C9 H9 119.1 . . ?
C8 C9 H9 119.1 . . ?
N2 C10 C11 122.3(7) . . ?
N2 C10 H10 118.9 . . ?
C11 C10 H10 118.9 . . ?
C10 C11 C12 118.9(8) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
C11 C12 C8 119.6(8) . . ?
C11 C12 H12 120.2 . . ?
C8 C12 H12 120.2 . . ?
C14 C13 C18 119.3(7) . . ?
C14 C13 H13 120.4 . . ?
C18 C13 H13 120.4 . . ?
C13 C14 C15 122.2(7) . . ?
C13 C14 Cl1 119.0(6) . . ?
C15 C14 Cl1 118.7(6) . . ?
C14 C15 C16 117.3(7) . . ?
C14 C15 H15 121.3 . . ?
C16 C15 H15 121.3 . . ?
C15 C16 C17 122.4(7) . . ?
C15 C16 Cl2 119.7(6) . . ?
C17 C16 Cl2 117.9(6) . . ?
C18 C17 C16 118.6(7) . . ?
C18 C17 H17 120.7 . . ?
C16 C17 H17 120.7 . . ?
C17 C18 C13 120.1(6) . . ?
C17 C18 C19 121.1(7) . . ?
C13 C18 C19 118.8(6) . . ?
O2 C19 O3 123.3(7) . . ?
O2 C19 C18 123.4(7) . . ?
O3 C19 C18 113.3(6) . . ?
C7 N1 C8 121.4(7) . . ?
C10 N2 C9 118.9(7) . . ?
C1 O1 H1A 109.5 . . ?
C19 O3 H3A 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
O1 C1 C2 C3 180.0(8) . . . . ?
C6 C1 C2 C3 0.6(13) . . . . ?
C1 C2 C3 C4 -0.6(14) . . . . ?
C2 C3 C4 C5 0.7(13) . . . . ?
C2 C3 C4 Br1 179.8(7) . . . . ?
C3 C4 C5 C6 -0.8(12) . . . . ?
Br1 C4 C5 C6 -179.8(6) . . . . ?
O1 C1 C6 C5 -180.0(8) . . . . ?
C2 C1 C6 C5 -0.6(12) . . . . ?
O1 C1 C6 C7 -0.9(13) . . . . ?
C2 C1 C6 C7 178.5(8) . . . . ?
C4 C5 C6 C1 0.7(11) . . . . ?
C4 C5 C6 C7 -178.4(7) . . . . ?
C1 C6 C7 N1 0.8(12) . . . . ?
C5 C6 C7 N1 179.9(7) . . . . ?
C12 C8 C9 N2 -2.1(12) . . . . ?
N1 C8 C9 N2 -179.2(7) . . . . ?
N2 C10 C11 C12 0.5(13) . . . . ?
C10 C11 C12 C8 -1.8(13) . . . . ?
C9 C8 C12 C11 2.5(12) . . . . ?
N1 C8 C12 C11 179.9(8) . . . . ?
C18 C13 C14 C15 -2.2(11) . . . . ?
C18 C13 C14 Cl1 177.4(6) . . . . ?
C13 C14 C15 C16 1.2(11) . . . . ?
Cl1 C14 C15 C16 -178.4(5) . . . . ?
C14 C15 C16 C17 -0.6(11) . . . . ?
C14 C15 C16 Cl2 179.9(6) . . . . ?
C15 C16 C17 C18 0.9(11) . . . . ?
Cl2 C16 C17 C18 -179.5(6) . . . . ?
C16 C17 C18 C13 -1.9(11) . . . . ?
C16 C17 C18 C19 179.6(7) . . . . ?
C14 C13 C18 C17 2.5(11) . . . . ?
C14 C13 C18 C19 -178.9(6) . . . . ?
C17 C18 C19 O2 179.3(8) . . . . ?
C13 C18 C19 O2 0.7(12) . . . . ?
C17 C18 C19 O3 -1.7(10) . . . . ?
C13 C18 C19 O3 179.7(7) . . . . ?
C6 C7 N1 C8 -178.7(7) . . . . ?
C12 C8 N1 C7 161.7(8) . . . . ?
C9 C8 N1 C7 -21.2(12) . . . . ?
C11 C10 N2 C9 0.1(12) . . . . ?
C8 C9 N2 C10 0.8(12) . . . . ?

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
_geom_hbond_publ_flag
C9 H9 O2 0.93 2.47 3.250(10) 141.1 1_545 yes
C10 H10 O3 0.93 2.67 3.582(10) 168.7 7_576 yes
C12 H12 Cl2 0.93 2.96 3.778(8) 148.1 6_576 yes
O1 H1A N1 0.82 1.87 2.588(8) 145.9 . yes
O3 H3A N2 0.82 1.80 2.616(8) 176.4 . yes

_refine_diff_density_max         0.937
_refine_diff_density_min         -0.945
_refine_diff_density_rms         0.108


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: THF'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC10
_database_code_depnum_ccdc_archive 'CCDC 1814052'
_audit_update_record             
;
2017-12-30 deposited with the CCDC.
2018-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
2,4-dibromo-6-[(E)-3-pyridyliminomethyl]phenol
_chemical_name_common            35Br-3SAP
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H8 Br2 N2 O'
_chemical_formula_sum            'C12 H8 Br2 N2 O'
_chemical_formula_weight         356.02

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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                   14.6532(3)
_cell_length_b                   4.52630(10)
_cell_length_c                   18.6301(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.499(2)
_cell_angle_gamma                90
_cell_volume                     1234.46(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    11311
_cell_measurement_theta_min      3.76
_cell_measurement_theta_max      68.21

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.916
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.138
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.088
_exptl_absorpt_coefficient_mu    8.209
_shelx_estimated_absorpt_T_min   0.397
_shelx_estimated_absorpt_T_max   0.532
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.336
_exptl_absorpt_correction_T_max  0.532
_exptl_absorpt_process_details   'Absorption was corrected by ABSCOR'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating anode X-ray tube'
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID IP Area Detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12010
_diffrn_reflns_av_unetI/netI     0.0573
_diffrn_reflns_av_R_equivalents  0.0865
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.759
_diffrn_reflns_theta_max         68.215
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2256
_reflns_number_gt                1916
_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       'PROCESS-AUTO (Rigaku, 1998)'
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'PROCESS-AUTO (Rigaku, 1998)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2008)'
_computing_publication_material  'SHELXL-2014/07 (Sheldrick, 2014)'
_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)+(0.0549P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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_number_reflns         2256
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.1027
_refine_ls_wR_factor_gt          0.0988
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
Br1 Br 0.70827(2) -0.41954(9) 0.36329(2) 0.05849(17) Uani 1 1 d . . . . .
O1 O 0.55240(15) -0.0065(6) 0.39292(11) 0.0516(6) Uani 1 1 d . . . . .
H1 H 0.518490 0.134705 0.398899 0.077 Uiso 1 1 calc R U . . .
N1 N 0.41729(16) 0.3509(6) 0.35884(13) 0.0425(6) Uani 1 1 d . . . . .
C1 C 0.55344(19) -0.0703(7) 0.32280(15) 0.0415(7) Uani 1 1 d . . . . .
Br2 Br 0.55876(3) -0.33084(13) 0.07958(2) 0.0851(2) Uani 1 1 d . . . . .
C2 C 0.6188(2) -0.2630(7) 0.29749(17) 0.0441(7) Uani 1 1 d . . . . .
N3 N 0.22033(19) 0.8695(7) 0.35313(16) 0.0608(8) Uani 1 1 d . . . . .
C3 C 0.6202(2) -0.3418(8) 0.22609(16) 0.0512(8) Uani 1 1 d . . . . .
H3 H 0.663819 -0.474059 0.210635 0.061 Uiso 1 1 calc R U . . .
C4 C 0.5563(2) -0.2222(8) 0.17765(17) 0.0528(8) Uani 1 1 d . . . . .
C5 C 0.4923(2) -0.0239(8) 0.19945(16) 0.0500(8) Uani 1 1 d . . . . .
H5 H 0.450437 0.057980 0.166136 0.060 Uiso 1 1 calc R U . . .
C6 C 0.49017(19) 0.0552(7) 0.27247(15) 0.0417(7) Uani 1 1 d . . . . .
C7 C 0.42379(19) 0.2729(7) 0.29346(16) 0.0437(7) Uani 1 1 d . . . . .
H7 H 0.385001 0.357736 0.258399 0.052 Uiso 1 1 calc R U . . .
C9 C 0.2824(2) 0.6724(8) 0.33349(18) 0.0546(8) Uani 1 1 d . . . . .
H9 H 0.278794 0.604870 0.286301 0.066 Uiso 1 1 calc R U . . .
C8 C 0.35200(18) 0.5616(7) 0.37880(15) 0.0399(6) Uani 1 1 d . . . . .
C10 C 0.2259(2) 0.9608(8) 0.42125(18) 0.0526(8) Uani 1 1 d . . . . .
H10 H 0.182795 1.095677 0.436203 0.063 Uiso 1 1 calc R U . . .
C11 C 0.2919(2) 0.8663(8) 0.47034(17) 0.0543(8) Uani 1 1 d . . . . .
H11 H 0.293510 0.937053 0.517243 0.065 Uiso 1 1 calc R U . . .
C12 C 0.3559(2) 0.6649(7) 0.44918(16) 0.0490(8) Uani 1 1 d . . . . .
H12 H 0.401370 0.598542 0.481676 0.059 Uiso 1 1 calc 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
Br1 C2 1.893(3) . ?
O1 C1 1.339(3) . ?
O1 H1 0.8200 . ?
N1 C7 1.276(4) . ?
N1 C8 1.412(4) . ?
C1 C2 1.393(4) . ?
C1 C6 1.409(4) . ?
Br2 C4 1.894(3) . ?
C2 C3 1.378(4) . ?
N3 C10 1.334(4) . ?
N3 C9 1.337(4) . ?
C3 C4 1.383(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(5) . ?
C5 C6 1.408(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.450(4) . ?
C7 H7 0.9300 . ?
C9 C8 1.389(4) . ?
C9 H9 0.9300 . ?
C8 C12 1.391(4) . ?
C10 C11 1.370(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.378(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C7 N1 C8 121.2(3) . . ?
O1 C1 C2 120.2(3) . . ?
O1 C1 C6 121.8(3) . . ?
C2 C1 C6 118.0(3) . . ?
C3 C2 C1 121.9(3) . . ?
C3 C2 Br1 119.2(2) . . ?
C1 C2 Br1 118.8(2) . . ?
C10 N3 C9 116.9(3) . . ?
C2 C3 C4 119.3(3) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 121.0(3) . . ?
C5 C4 Br2 119.8(3) . . ?
C3 C4 Br2 119.1(3) . . ?
C4 C5 C6 119.7(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C1 119.9(3) . . ?
C5 C6 C7 118.4(3) . . ?
C1 C6 C7 121.6(3) . . ?
N1 C7 C6 121.6(3) . . ?
N1 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
N3 C9 C8 124.4(3) . . ?
N3 C9 H9 117.8 . . ?
C8 C9 H9 117.8 . . ?
C9 C8 C12 116.8(3) . . ?
C9 C8 N1 124.9(3) . . ?
C12 C8 N1 118.3(3) . . ?
N3 C10 C11 123.4(3) . . ?
N3 C10 H10 118.3 . . ?
C11 C10 H10 118.3 . . ?
C10 C11 C12 119.0(3) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C11 C12 C8 119.4(3) . . ?
C11 C12 H12 120.3 . . ?
C8 C12 H12 120.3 . . ?

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
O1 C1 C2 C3 177.8(3) . . . . ?
C6 C1 C2 C3 -2.8(4) . . . . ?
O1 C1 C2 Br1 -2.4(4) . . . . ?
C6 C1 C2 Br1 177.0(2) . . . . ?
C1 C2 C3 C4 1.3(5) . . . . ?
Br1 C2 C3 C4 -178.5(2) . . . . ?
C2 C3 C4 C5 0.8(5) . . . . ?
C2 C3 C4 Br2 179.9(2) . . . . ?
C3 C4 C5 C6 -1.3(5) . . . . ?
Br2 C4 C5 C6 179.6(2) . . . . ?
C4 C5 C6 C1 -0.2(5) . . . . ?
C4 C5 C6 C7 177.9(3) . . . . ?
O1 C1 C6 C5 -178.4(3) . . . . ?
C2 C1 C6 C5 2.3(4) . . . . ?
O1 C1 C6 C7 3.5(4) . . . . ?
C2 C1 C6 C7 -175.8(3) . . . . ?
C8 N1 C7 C6 -179.6(3) . . . . ?
C5 C6 C7 N1 178.9(3) . . . . ?
C1 C6 C7 N1 -3.0(4) . . . . ?
C10 N3 C9 C8 -0.8(6) . . . . ?
N3 C9 C8 C12 0.2(5) . . . . ?
N3 C9 C8 N1 179.2(3) . . . . ?
C7 N1 C8 C9 9.0(5) . . . . ?
C7 N1 C8 C12 -172.0(3) . . . . ?
C9 N3 C10 C11 1.0(5) . . . . ?
N3 C10 C11 C12 -0.5(5) . . . . ?
C10 C11 C12 C8 -0.2(5) . . . . ?
C9 C8 C12 C11 0.3(5) . . . . ?
N1 C8 C12 C11 -178.8(3) . . . . ?

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
O1 H1 N1 0.82 1.90 2.613(3) 144.5 .
C3 H3 Br1 0.93 3.11 4.036(3) 171.1 2_645
C7 H7 N3 0.93 2.53 3.407(4) 156.4 2_545
C11 H11 Br1 0.93 3.12 3.985(3) 155.6 3_666

_refine_diff_density_max         0.621
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.102


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate'
_chemical_compound_source        non-photochromic
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC11
_database_code_depnum_ccdc_archive 'CCDC 1814051'
_audit_update_record             
;
2017-12-30 deposited with the CCDC.
2018-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
2,4-dichloro6-[(E)-3-pyridyliminomethyl]phenol
_chemical_name_common            35Cl-3SAP
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H8 Cl2 N2 O'
_chemical_formula_sum            'C12 H8 Cl2 N2 O'
_chemical_formula_weight         267.10

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   26.1636(6)
_cell_length_b                   3.80910(10)
_cell_length_c                   34.4455(6)
_cell_angle_alpha                90
_cell_angle_beta                 137.4640(10)
_cell_angle_gamma                90
_cell_volume                     2320.77(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    11218
_cell_measurement_theta_min      3.380
_cell_measurement_theta_max      68.135

_exptl_crystal_description       platelet
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_F_000             1088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    4.900
_shelx_estimated_absorpt_T_min   0.456
_shelx_estimated_absorpt_T_max   0.792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.513
_exptl_absorpt_correction_T_max  0.783
_exptl_absorpt_process_details   abscore,T.Higashi,RIGAKU
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating anode x-ray'
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID2'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            11218
_diffrn_reflns_av_unetI/netI     0.0656
_diffrn_reflns_av_R_equivalents  0.0959
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         3.380
_diffrn_reflns_theta_max         68.135
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2131
_reflns_number_gt                1777
_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       RAPID-AUTO
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        RAPID-AUTO
_computing_structure_solution    'SHELXS-97(Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
; 
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. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0763P)²] 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         2131
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1315
_refine_ls_wR_factor_gt          0.1208
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_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
Cl1 Cl 0.14710(3) 1.10514(14) -0.02538(2) 0.0550(2) Uani 1 1 d . . . . .
Cl2 Cl 0.41625(3) 0.57358(18) 0.16919(3) 0.0673(2) Uani 1 1 d . . . . .
O1 O 0.10116(8) 0.9450(4) 0.02825(6) 0.0535(4) Uani 1 1 d . . . . .
H1 H 0.0906 0.8940 0.0448 0.080 Uiso 1 1 calc R U . . .
N1 N 0.12625(9) 0.7104(4) 0.11342(7) 0.0452(4) Uani 1 1 d . . . . .
N2 N 0.14179(10) 0.6963(5) 0.22896(7) 0.0528(5) Uani 1 1 d . . . . .
C1 C 0.17374(11) 0.8603(5) 0.06169(8) 0.0419(4) Uani 1 1 d . . . . .
C2 C 0.20442(11) 0.9230(5) 0.04233(8) 0.0428(5) Uani 1 1 d . . . . .
C3 C 0.27823(12) 0.8404(5) 0.07471(9) 0.0466(5) Uani 1 1 d . . . . .
H3 H 0.2974 0.8854 0.0608 0.056 Uiso 1 1 calc R U . . .
C4 C 0.32372(11) 0.6883(5) 0.12860(9) 0.0454(5) Uani 1 1 d . . . . .
C5 C 0.29548(11) 0.6218(5) 0.14915(9) 0.0446(5) Uani 1 1 d . . . . .
H2 H 0.3262 0.5190 0.1851 0.054 Uiso 1 1 calc R U . . .
C6 C 0.22066(11) 0.7083(5) 0.11621(8) 0.0414(4) Uani 1 1 d . . . . .
C7 C 0.19359(12) 0.6351(5) 0.14015(9) 0.0433(5) Uani 1 1 d . . . . .
H7 H 0.2263 0.5300 0.1761 0.052 Uiso 1 1 calc R U . . .
C8 C 0.10695(10) 0.6512(5) 0.14212(8) 0.0405(4) Uani 1 1 d . . . . .
C9 C 0.15597(11) 0.7439(6) 0.19921(9) 0.0465(5) Uani 1 1 d . . . . .
H9 H 0.2018 0.8463 0.2181 0.056 Uiso 1 1 calc R U . . .
C10 C 0.07508(13) 0.5525(6) 0.20035(10) 0.0542(5) Uani 1 1 d . . . . .
H10 H 0.0640 0.5108 0.2202 0.065 Uiso 1 1 calc R U . . .
C11 C 0.02203(12) 0.4629(6) 0.14344(9) 0.0507(5) Uani 1 1 d . . . . .
H11 H -0.0241 0.3687 0.1253 0.061 Uiso 1 1 calc R U . . .
C12 C 0.03746(11) 0.5132(6) 0.11297(9) 0.0481(5) Uani 1 1 d . . . . .
H12 H 0.0021 0.4558 0.0742 0.058 Uiso 1 1 calc 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
Cl1 C2 1.736(2) . ?
Cl2 C4 1.737(2) . ?
O1 C1 1.347(2) . ?
O1 H1 0.8200 . ?
N1 C7 1.282(2) . ?
N1 C8 1.421(2) . ?
N2 C9 1.335(2) . ?
N2 C10 1.335(3) . ?
C1 C2 1.391(3) . ?
C1 C6 1.404(3) . ?
C2 C3 1.378(3) . ?
C3 C4 1.393(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(3) . ?
C5 C6 1.398(3) . ?
C5 H2 0.9300 . ?
C6 C7 1.456(2) . ?
C7 H7 0.9300 . ?
C8 C12 1.378(2) . ?
C8 C9 1.386(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.370(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.387(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C7 N1 C8 118.01(18) . . ?
C9 N2 C10 116.17(18) . . ?
O1 C1 C2 119.79(18) . . ?
O1 C1 C6 122.35(17) . . ?
C2 C1 C6 117.86(18) . . ?
C3 C2 C1 122.17(19) . . ?
C3 C2 Cl1 119.13(15) . . ?
C1 C2 Cl1 118.69(16) . . ?
C2 C3 C4 119.03(18) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 120.53(19) . . ?
C5 C4 Cl2 119.95(16) . . ?
C3 C4 Cl2 119.51(15) . . ?
C4 C5 C6 120.14(19) . . ?
C4 C5 H2 119.9 . . ?
C6 C5 H2 119.9 . . ?
C5 C6 C1 120.27(17) . . ?
C5 C6 C7 118.02(18) . . ?
C1 C6 C7 121.71(18) . . ?
N1 C7 C6 122.34(19) . . ?
N1 C7 H7 118.8 . . ?
C6 C7 H7 118.8 . . ?
C12 C8 C9 118.39(18) . . ?
C12 C8 N1 120.54(17) . . ?
C9 C8 N1 121.02(17) . . ?
N2 C9 C8 124.39(19) . . ?
N2 C9 H9 117.8 . . ?
C8 C9 H9 117.8 . . ?
N2 C10 C11 123.6(2) . . ?
N2 C10 H10 118.2 . . ?
C11 C10 H10 118.2 . . ?
C10 C11 C12 119.7(2) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C8 C12 C11 117.69(19) . . ?
C8 C12 H12 121.2 . . ?
C11 C12 H12 121.2 . . ?

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
O1 C1 C2 C3 -179.77(18) . . . . ?
C6 C1 C2 C3 0.1(3) . . . . ?
O1 C1 C2 Cl1 -0.8(2) . . . . ?
C6 C1 C2 Cl1 179.10(14) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
Cl1 C2 C3 C4 -178.84(15) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C2 C3 C4 Cl2 178.55(15) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
Cl2 C4 C5 C6 -178.91(15) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C4 C5 C6 C7 -179.49(17) . . . . ?
O1 C1 C6 C5 179.40(18) . . . . ?
C2 C1 C6 C5 -0.5(3) . . . . ?
O1 C1 C6 C7 -0.5(3) . . . . ?
C2 C1 C6 C7 179.62(17) . . . . ?
C8 N1 C7 C6 -175.65(16) . . . . ?
C5 C6 C7 N1 178.90(18) . . . . ?
C1 C6 C7 N1 -1.2(3) . . . . ?
C7 N1 C8 C12 -139.3(2) . . . . ?
C7 N1 C8 C9 43.5(3) . . . . ?
C10 N2 C9 C8 -0.7(3) . . . . ?
C12 C8 C9 N2 2.7(3) . . . . ?
N1 C8 C9 N2 -179.94(19) . . . . ?
C9 N2 C10 C11 -1.5(3) . . . . ?
N2 C10 C11 C12 1.6(4) . . . . ?
C9 C8 C12 C11 -2.5(3) . . . . ?
N1 C8 C12 C11 -179.79(18) . . . . ?
C10 C11 C12 C8 0.5(3) . . . . ?

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
O1 H1 N1 0.82 1.92 2.646(2) 146.6 .

_refine_diff_density_max         0.401
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.077


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: diethyl ether'
_chemical_compound_source        photochromic
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC12
_database_code_depnum_ccdc_archive 'CCDC 1814063'
_audit_update_record             
;
2017-12-30 deposited with the CCDC.
2018-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
'4-chloro-2-[(E)-3-pyridyliminomethyl]phenol, 4-chlorobenzoic acid'
_chemical_name_common            5Cl3SAP-4ClBA
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 Cl N2 O, C7 H5 Cl O2'
_chemical_formula_sum            'C19 H14 Cl2 N2 O3'
_chemical_formula_weight         389.22

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   32.818(8)
_cell_length_b                   6.2380(15)
_cell_length_c                   18.465(5)
_cell_angle_alpha                90
_cell_angle_beta                 109.440(4)
_cell_angle_gamma                90
_cell_volume                     3564.7(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    16488
_cell_measurement_theta_min      3.043
_cell_measurement_theta_max      27.367

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_F_000             1600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.386
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.603
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   abscore,T.Higashi,RIGAKU
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode x-ray'
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            16488
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.043
_diffrn_reflns_theta_max         27.367
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4021
_reflns_number_gt                2451
_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       RAPID-AUTO
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        RAPID-AUTO
_computing_structure_solution    'SHELXS-97(Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
; 
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. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0724P)²+1.0038P] 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         4021
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1481
_refine_ls_wR_factor_gt          0.1141
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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
Cl1 Cl 0.69854(2) -0.09536(15) 1.00004(5) 0.0950(3) Uani 1 1 d . . . . .
Cl2 Cl 0.24737(2) 0.99928(15) 0.15076(5) 0.0905(3) Uani 1 1 d . . . . .
O1 O 0.56958(6) 0.5250(3) 0.82028(10) 0.0657(5) Uani 1 1 d . . . . .
H1A H 0.555278 0.475404 0.778403 0.099 Uiso 1 1 calc R U . . .
O2 O 0.41078(5) 0.5430(3) 0.42318(9) 0.0629(4) Uani 1 1 d . . . . .
H2A H 0.428514 0.456947 0.449252 0.094 Uiso 1 1 calc R U . . .
O3 O 0.39761(7) 0.2790(3) 0.33813(11) 0.0857(6) Uani 1 1 d . . . . .
N1 N 0.54191(5) 0.2308(3) 0.71517(10) 0.0470(4) Uani 1 1 d . . . . .
N2 N 0.46308(6) 0.2629(3) 0.52192(11) 0.0544(5) Uani 1 1 d . . . . .
C1 C 0.60092(6) 0.1709(4) 0.83077(12) 0.0473(5) Uani 1 1 d . . . . .
C2 C 0.59877(7) 0.3774(4) 0.85994(13) 0.0527(5) Uani 1 1 d . . . . .
C3 C 0.62731(8) 0.4334(5) 0.93192(15) 0.0662(7) Uani 1 1 d . . . . .
H3 H 0.625921 0.569500 0.951501 0.079 Uiso 1 1 calc R U . . .
C4 C 0.65736(8) 0.2900(5) 0.97408(15) 0.0709(7) Uani 1 1 d . . . . .
H4 H 0.676307 0.329128 1.022082 0.085 Uiso 1 1 calc R U . . .
C5 C 0.65972(7) 0.0857(5) 0.94548(15) 0.0642(6) Uani 1 1 d . . . . .
C6 C 0.63185(7) 0.0267(4) 0.87462(14) 0.0557(5) Uani 1 1 d . . . . .
H6 H 0.633606 -0.109965 0.855772 0.067 Uiso 1 1 calc R U . . .
C7 C 0.57103(6) 0.1034(3) 0.75681(12) 0.0472(5) Uani 1 1 d . . . . .
H7 H 0.573046 -0.034764 0.739349 0.057 Uiso 1 1 calc R U . . .
C8 C 0.51104(6) 0.1580(3) 0.64594(12) 0.0446(5) Uani 1 1 d . . . . .
C9 C 0.49370(6) 0.3081(4) 0.58851(13) 0.0500(5) Uani 1 1 d . . . . .
H9 H 0.504000 0.447969 0.596896 0.060 Uiso 1 1 calc R U . . .
C10 C 0.44837(7) 0.0606(4) 0.51022(14) 0.0573(6) Uani 1 1 d . . . . .
H10 H 0.427544 0.025837 0.463541 0.069 Uiso 1 1 calc R U . . .
C11 C 0.46304(7) -0.0975(4) 0.56489(14) 0.0566(6) Uani 1 1 d . . . . .
H11 H 0.451692 -0.235350 0.555536 0.068 Uiso 1 1 calc R U . . .
C12 C 0.49474(7) -0.0493(4) 0.63369(14) 0.0535(5) Uani 1 1 d . . . . .
H12 H 0.505008 -0.154030 0.671220 0.064 Uiso 1 1 calc R U . . .
C13 C 0.35395(6) 0.5927(4) 0.30650(12) 0.0489(5) Uani 1 1 d . . . . .
C14 C 0.32874(7) 0.5153(4) 0.23438(14) 0.0575(6) Uani 1 1 d . . . . .
H14 H 0.334173 0.380033 0.218509 0.069 Uiso 1 1 calc R U . . .
C15 C 0.29586(7) 0.6391(4) 0.18677(14) 0.0631(6) Uani 1 1 d . . . . .
H15 H 0.278999 0.587783 0.138886 0.076 Uiso 1 1 calc R U . . .
C16 C 0.28826(7) 0.8395(4) 0.21087(14) 0.0596(6) Uani 1 1 d . . . . .
C17 C 0.31232(7) 0.9192(4) 0.28179(15) 0.0614(6) Uani 1 1 d . . . . .
H17 H 0.306532 1.054146 0.297494 0.074 Uiso 1 1 calc R U . . .
C18 C 0.34537(7) 0.7937(4) 0.32925(13) 0.0554(5) Uani 1 1 d . . . . .
H18 H 0.362020 0.845820 0.377156 0.066 Uiso 1 1 calc R U . . .
C19 C 0.38921(7) 0.4555(4) 0.35643(14) 0.0548(5) 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
Cl1 C5 1.749(3) . ?
Cl2 C16 1.742(2) . ?
O1 C2 1.354(3) . ?
O1 H1A 0.8200 . ?
O2 C19 1.318(3) . ?
O2 H2A 0.8200 . ?
O3 C19 1.210(3) . ?
N1 C7 1.284(3) . ?
N1 C8 1.416(3) . ?
N2 C9 1.334(3) . ?
N2 C10 1.343(3) . ?
C1 C6 1.396(3) . ?
C1 C2 1.407(3) . ?
C1 C7 1.454(3) . ?
C2 C3 1.392(3) . ?
C3 C4 1.366(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.387(3) . ?
C8 C12 1.389(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.378(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.381(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C18 1.381(3) . ?
C13 C14 1.399(3) . ?
C13 C19 1.487(3) . ?
C14 C15 1.379(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.377(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.378(3) . ?
C17 C18 1.387(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?

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 H1A 109.5 . . ?
C19 O2 H2A 109.5 . . ?
C7 N1 C8 120.58(18) . . ?
C9 N2 C10 117.8(2) . . ?
C6 C1 C2 119.2(2) . . ?
C6 C1 C7 119.4(2) . . ?
C2 C1 C7 121.4(2) . . ?
O1 C2 C3 118.4(2) . . ?
O1 C2 C1 122.1(2) . . ?
C3 C2 C1 119.4(2) . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 120.3(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 120.2(2) . . ?
C6 C5 Cl1 120.1(2) . . ?
C4 C5 Cl1 119.7(2) . . ?
C5 C6 C1 120.3(2) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
N1 C7 C1 121.22(19) . . ?
N1 C7 H7 119.4 . . ?
C1 C7 H7 119.4 . . ?
C9 C8 C12 117.8(2) . . ?
C9 C8 N1 117.53(19) . . ?
C12 C8 N1 124.5(2) . . ?
N2 C9 C8 123.6(2) . . ?
N2 C9 H9 118.2 . . ?
C8 C9 H9 118.2 . . ?
N2 C10 C11 122.4(2) . . ?
N2 C10 H10 118.8 . . ?
C11 C10 H10 118.8 . . ?
C10 C11 C12 119.4(2) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C11 C12 C8 118.9(2) . . ?
C11 C12 H12 120.5 . . ?
C8 C12 H12 120.5 . . ?
C18 C13 C14 119.2(2) . . ?
C18 C13 C19 122.0(2) . . ?
C14 C13 C19 118.9(2) . . ?
C15 C14 C13 120.2(2) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C14 119.3(2) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C16 C17 121.8(2) . . ?
C15 C16 Cl2 119.83(19) . . ?
C17 C16 Cl2 118.4(2) . . ?
C16 C17 C18 118.5(2) . . ?
C16 C17 H17 120.8 . . ?
C18 C17 H17 120.8 . . ?
C13 C18 C17 121.1(2) . . ?
C13 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
O3 C19 O2 122.4(2) . . ?
O3 C19 C13 123.6(2) . . ?
O2 C19 C13 114.0(2) . . ?

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 179.9(2) . . . . ?
C7 C1 C2 O1 -1.5(3) . . . . ?
C6 C1 C2 C3 -0.3(3) . . . . ?
C7 C1 C2 C3 178.3(2) . . . . ?
O1 C2 C3 C4 -179.9(2) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C2 C3 C4 C5 -0.1(4) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C3 C4 C5 Cl1 179.7(2) . . . . ?
C4 C5 C6 C1 -0.1(4) . . . . ?
Cl1 C5 C6 C1 -179.79(17) . . . . ?
C2 C1 C6 C5 0.2(3) . . . . ?
C7 C1 C6 C5 -178.4(2) . . . . ?
C8 N1 C7 C1 -175.37(17) . . . . ?
C6 C1 C7 N1 179.39(19) . . . . ?
C2 C1 C7 N1 0.8(3) . . . . ?
C7 N1 C8 C9 -152.18(19) . . . . ?
C7 N1 C8 C12 32.6(3) . . . . ?
C10 N2 C9 C8 0.0(3) . . . . ?
C12 C8 C9 N2 -1.5(3) . . . . ?
N1 C8 C9 N2 -177.07(18) . . . . ?
C9 N2 C10 C11 1.6(3) . . . . ?
N2 C10 C11 C12 -1.6(3) . . . . ?
C10 C11 C12 C8 0.0(3) . . . . ?
C9 C8 C12 C11 1.5(3) . . . . ?
N1 C8 C12 C11 176.68(19) . . . . ?
C18 C13 C14 C15 0.2(3) . . . . ?
C19 C13 C14 C15 -179.9(2) . . . . ?
C13 C14 C15 C16 0.2(4) . . . . ?
C14 C15 C16 C17 -0.8(4) . . . . ?
C14 C15 C16 Cl2 179.03(18) . . . . ?
C15 C16 C17 C18 0.9(4) . . . . ?
Cl2 C16 C17 C18 -178.94(18) . . . . ?
C14 C13 C18 C17 -0.1(3) . . . . ?
C19 C13 C18 C17 180.0(2) . . . . ?
C16 C17 C18 C13 -0.4(3) . . . . ?
C18 C13 C19 O3 -179.8(2) . . . . ?
C14 C13 C19 O3 0.2(3) . . . . ?
C18 C13 C19 O2 0.3(3) . . . . ?
C14 C13 C19 O2 -179.64(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
O1 H1A N1 0.82 1.88 2.605(2) 146.4 .
O2 H2A N2 0.82 1.88 2.691(2) 169.1 .
C4 H4 Cl2 0.93 2.92 3.829(3) 166.1 3_546
C7 H7 O3 0.93 2.49 3.320(3) 148.3 5_656

_refine_diff_density_max         0.273
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.053


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: THF'
_chemical_compound_source        photochromic
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC13
_database_code_depnum_ccdc_archive 'CCDC 1814064'
_audit_update_record             
;
2017-12-30 deposited with the CCDC.
2018-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
'2,4-dibromo-6-[(E)-3-pyridyliminomethyl]phenol, 3,5-dinitrobenzoic acid'
_chemical_name_common            35Br3SAP-35NO2BA
_chemical_formula_moiety         'C12 H8 Br2 N2 O , C7 H4 N2 O6'
_chemical_melting_point          ?
_chemical_formula_sum            'C19 H12 Br2 N4 O7'
_chemical_formula_weight         568.15

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      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

_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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   37.206(3)
_cell_length_b                   7.3594(6)
_cell_length_c                   7.5694(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.589(2)
_cell_angle_gamma                90
_cell_volume                     2071.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7226
_cell_measurement_theta_min      3.22
_cell_measurement_theta_max      27.4

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.821
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    3.964
_shelx_estimated_absorpt_T_min   0.670
_shelx_estimated_absorpt_T_max   0.925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.52
_exptl_absorpt_correction_T_max  0.925
_exptl_absorpt_process_details   'Absorption was corrected by ABSCOR'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode X-ray tube'
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID IP Area Detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10066
_diffrn_reflns_av_unetI/netI     0.0993
_diffrn_reflns_av_R_equivalents  0.0663
_diffrn_reflns_limit_h_min       -48
_diffrn_reflns_limit_h_max       47
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.219
_diffrn_reflns_theta_max         27.415
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4666
_reflns_number_gt                2856
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.838
_reflns_Friedel_fraction_max     0.976
_reflns_Friedel_fraction_full    0.995

_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       'PROCESS-AUTO (Rigaku, 1998)'
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'PROCESS-AUTO (Rigaku, 1998)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2008)'
_computing_publication_material  'SHELXL-2014/07 (Sheldrick, 2014)'
_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)+(0.0495P)²+0.3575P] 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 x determined using 927 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.002(12)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4666
_refine_ls_number_parameters     291
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.1427
_refine_ls_wR_factor_gt          0.1044
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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
Br1 Br 0.38470(2) 0.66758(13) 0.71394(12) 0.0649(3) Uani 1 1 d . . . . .
Br2 Br 0.27191(2) 0.1721(2) 0.57276(14) 0.0811(4) Uani 1 1 d . . . . .
O1 O 0.42849(16) 0.3734(9) 0.5435(10) 0.0608(16) Uani 1 1 d . . . . .
H1A H 0.440001 0.292809 0.496159 0.091 Uiso 1 1 calc R U . . .
O2 O 0.55817(15) 0.2605(10) 0.0208(10) 0.072(2) Uani 1 1 d . . . . .
O3 O 0.58112(15) -0.0093(10) 0.0937(11) 0.0684(19) Uani 1 1 d . . . . .
H3A H 0.560763 -0.030427 0.127092 0.103 Uiso 1 1 calc R U . . .
O4 O 0.64251(19) 0.7065(10) -0.2176(10) 0.082(2) Uani 1 1 d . . . . .
O5 O 0.69662(19) 0.6290(12) -0.2773(11) 0.092(3) Uani 1 1 d . . . . .
O6 O 0.74134(19) 0.0387(12) -0.0788(13) 0.100(3) Uani 1 1 d . . . . .
O7 O 0.7064(2) -0.1338(14) 0.0719(13) 0.101(3) Uani 1 1 d . . . . .
N1 N 0.44003(18) 0.0589(10) 0.4000(10) 0.0495(17) Uani 1 1 d . . . . .
N2 N 0.51997(18) -0.1267(12) 0.1971(10) 0.0557(19) Uani 1 1 d . . . . .
N3 N 0.6671(2) 0.5974(11) -0.2142(11) 0.059(2) Uani 1 1 d . . . . .
N4 N 0.7125(2) 0.0028(14) -0.0149(12) 0.068(2) Uani 1 1 d . . . . .
C1 C 0.3936(2) 0.3235(11) 0.5502(11) 0.0458(19) Uani 1 1 d . . . . .
C2 C 0.3686(2) 0.4430(13) 0.6227(11) 0.054(2) Uani 1 1 d . . . . .
C3 C 0.3332(2) 0.3977(13) 0.6267(11) 0.052(2) Uani 1 1 d . . . . .
H3 H 0.316531 0.478600 0.671555 0.063 Uiso 1 1 calc R U . . .
C4 C 0.3223(2) 0.2305(13) 0.5634(12) 0.056(2) Uani 1 1 d . . . . .
C5 C 0.34575(19) 0.1083(12) 0.4947(11) 0.047(2) Uani 1 1 d . . . . .
H5 H 0.337657 -0.004000 0.453824 0.056 Uiso 1 1 calc R U . . .
C6 C 0.38163(19) 0.1542(16) 0.4870(9) 0.0457(17) Uani 1 1 d . . . . .
C7 C 0.4063(2) 0.0244(13) 0.4118(12) 0.049(2) Uani 1 1 d . . . . .
H7 H 0.397415 -0.086639 0.371111 0.059 Uiso 1 1 calc R U . . .
C8 C 0.4634(2) -0.0746(12) 0.3294(11) 0.048(2) Uani 1 1 d . . . . .
C9 C 0.4572(2) -0.2601(13) 0.3351(13) 0.059(2) Uani 1 1 d . . . . .
H9 H 0.436287 -0.305959 0.382563 0.071 Uiso 1 1 calc R U . . .
C10 C 0.4828(2) -0.3754(13) 0.2686(13) 0.065(3) Uani 1 1 d . . . . .
H10 H 0.479207 -0.500410 0.268837 0.078 Uiso 1 1 calc R U . . .
C11 C 0.5138(2) -0.3031(15) 0.2020(12) 0.056(2) Uani 1 1 d . . . . .
H11 H 0.530997 -0.381744 0.158736 0.067 Uiso 1 1 calc R U . . .
C12 C 0.4950(2) -0.0133(13) 0.2588(12) 0.054(2) Uani 1 1 d . . . . .
H12 H 0.499145 0.111153 0.253804 0.065 Uiso 1 1 calc R U . . .
C13 C 0.62695(19) 0.3758(12) -0.0867(11) 0.0434(18) Uani 1 1 d . . . . .
H13 H 0.608297 0.458527 -0.104468 0.052 Uiso 1 1 calc R U . . .
C14 C 0.6617(2) 0.4190(12) -0.1332(11) 0.048(2) Uani 1 1 d . . . . .
C15 C 0.6903(2) 0.3009(13) -0.1132(12) 0.051(2) Uani 1 1 d . . . . .
H15 H 0.713246 0.332191 -0.147960 0.062 Uiso 1 1 calc R U . . .
C16 C 0.68319(18) 0.1344(13) -0.0394(11) 0.047(2) Uani 1 1 d . . . . .
C17 C 0.6490(2) 0.0838(12) 0.0124(11) 0.049(2) Uani 1 1 d . . . . .
H17 H 0.645115 -0.029337 0.063170 0.059 Uiso 1 1 calc R U . . .
C18 C 0.62059(19) 0.2064(12) -0.0132(10) 0.045(2) Uani 1 1 d . . . . .
C19 C 0.58272(19) 0.1573(18) 0.0358(10) 0.0491(18) 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
Br1 C2 1.883(10) . ?
Br2 C4 1.927(9) . ?
O1 C1 1.350(9) . ?
O1 H1A 0.8200 . ?
O2 C19 1.191(11) . ?
O3 C19 1.304(14) . ?
O3 H3A 0.8200 . ?
O4 N3 1.217(10) . ?
O5 N3 1.231(10) . ?
O6 N4 1.219(12) . ?
O7 N4 1.226(12) . ?
N1 C7 1.288(10) . ?
N1 C8 1.426(11) . ?
N2 C11 1.319(14) . ?
N2 C12 1.342(12) . ?
N3 C14 1.465(12) . ?
N4 C16 1.466(12) . ?
C1 C6 1.403(13) . ?
C1 C2 1.405(13) . ?
C2 C3 1.359(11) . ?
C3 C4 1.378(13) . ?
C3 H3 0.9300 . ?
C4 C5 1.365(12) . ?
C5 C6 1.380(10) . ?
C5 H5 0.9300 . ?
C6 C7 1.451(13) . ?
C7 H7 0.9300 . ?
C8 C12 1.381(12) . ?
C8 C9 1.385(13) . ?
C9 C10 1.381(12) . ?
C9 H9 0.9300 . ?
C10 C11 1.377(12) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.388(11) . ?
C13 C18 1.389(12) . ?
C13 H13 0.9300 . ?
C14 C15 1.378(12) . ?
C15 C16 1.375(13) . ?
C15 H15 0.9300 . ?
C16 C17 1.393(11) . ?
C17 C18 1.399(11) . ?
C17 H17 0.9300 . ?
C18 C19 1.510(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1A 109.5 . . ?
C19 O3 H3A 109.5 . . ?
C7 N1 C8 119.8(8) . . ?
C11 N2 C12 118.6(8) . . ?
O4 N3 O5 123.1(9) . . ?
O4 N3 C14 119.2(8) . . ?
O5 N3 C14 117.7(9) . . ?
O6 N4 O7 124.7(10) . . ?
O6 N4 C16 117.8(10) . . ?
O7 N4 C16 117.5(9) . . ?
O1 C1 C6 121.7(7) . . ?
O1 C1 C2 119.6(8) . . ?
C6 C1 C2 118.7(7) . . ?
C3 C2 C1 120.6(9) . . ?
C3 C2 Br1 120.4(7) . . ?
C1 C2 Br1 119.0(6) . . ?
C2 C3 C4 119.1(9) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 122.5(8) . . ?
C5 C4 Br2 120.0(6) . . ?
C3 C4 Br2 117.6(7) . . ?
C4 C5 C6 119.0(9) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C5 C6 C1 120.1(8) . . ?
C5 C6 C7 118.5(9) . . ?
C1 C6 C7 121.3(7) . . ?
N1 C7 C6 121.7(8) . . ?
N1 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C12 C8 C9 118.6(9) . . ?
C12 C8 N1 117.0(8) . . ?
C9 C8 N1 124.3(8) . . ?
C10 C9 C8 118.5(8) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
C11 C10 C9 119.2(9) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
N2 C11 C10 122.6(9) . . ?
N2 C11 H11 118.7 . . ?
C10 C11 H11 118.7 . . ?
N2 C12 C8 122.5(9) . . ?
N2 C12 H12 118.8 . . ?
C8 C12 H12 118.8 . . ?
C14 C13 C18 118.6(7) . . ?
C14 C13 H13 120.7 . . ?
C18 C13 H13 120.7 . . ?
C15 C14 C13 123.3(9) . . ?
C15 C14 N3 119.8(8) . . ?
C13 C14 N3 116.8(8) . . ?
C16 C15 C14 116.8(8) . . ?
C16 C15 H15 121.6 . . ?
C14 C15 H15 121.6 . . ?
C15 C16 C17 122.7(8) . . ?
C15 C16 N4 119.3(8) . . ?
C17 C16 N4 118.0(9) . . ?
C16 C17 C18 118.8(8) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
C13 C18 C17 119.9(7) . . ?
C13 C18 C19 118.9(8) . . ?
C17 C18 C19 121.2(8) . . ?
O2 C19 O3 126.1(8) . . ?
O2 C19 C18 122.8(11) . . ?
O3 C19 C18 111.0(8) . . ?

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
O1 C1 C2 C3 178.3(8) . . . . ?
C6 C1 C2 C3 -2.0(12) . . . . ?
O1 C1 C2 Br1 -1.5(11) . . . . ?
C6 C1 C2 Br1 178.2(6) . . . . ?
C1 C2 C3 C4 1.9(13) . . . . ?
Br1 C2 C3 C4 -178.3(6) . . . . ?
C2 C3 C4 C5 -0.7(14) . . . . ?
C2 C3 C4 Br2 179.7(6) . . . . ?
C3 C4 C5 C6 -0.5(13) . . . . ?
Br2 C4 C5 C6 179.1(6) . . . . ?
C4 C5 C6 C1 0.5(12) . . . . ?
C4 C5 C6 C7 -179.2(8) . . . . ?
O1 C1 C6 C5 -179.5(8) . . . . ?
C2 C1 C6 C5 0.8(12) . . . . ?
O1 C1 C6 C7 0.2(12) . . . . ?
C2 C1 C6 C7 -179.6(8) . . . . ?
C8 N1 C7 C6 178.3(8) . . . . ?
C5 C6 C7 N1 179.7(7) . . . . ?
C1 C6 C7 N1 0.0(13) . . . . ?
C7 N1 C8 C12 156.5(8) . . . . ?
C7 N1 C8 C9 -26.7(13) . . . . ?
C12 C8 C9 C10 -0.5(14) . . . . ?
N1 C8 C9 C10 -177.2(8) . . . . ?
C8 C9 C10 C11 1.1(15) . . . . ?
C12 N2 C11 C10 -0.3(14) . . . . ?
C9 C10 C11 N2 -0.7(15) . . . . ?
C11 N2 C12 C8 1.0(13) . . . . ?
C9 C8 C12 N2 -0.6(14) . . . . ?
N1 C8 C12 N2 176.4(8) . . . . ?
C18 C13 C14 C15 1.3(13) . . . . ?
C18 C13 C14 N3 178.6(7) . . . . ?
O4 N3 C14 C15 -173.8(8) . . . . ?
O5 N3 C14 C15 6.7(12) . . . . ?
O4 N3 C14 C13 8.8(12) . . . . ?
O5 N3 C14 C13 -170.7(8) . . . . ?
C13 C14 C15 C16 -1.5(13) . . . . ?
N3 C14 C15 C16 -178.7(7) . . . . ?
C14 C15 C16 C17 0.5(13) . . . . ?
C14 C15 C16 N4 180.0(8) . . . . ?
O6 N4 C16 C15 -7.9(13) . . . . ?
O7 N4 C16 C15 170.6(9) . . . . ?
O6 N4 C16 C17 171.6(9) . . . . ?
O7 N4 C16 C17 -9.9(13) . . . . ?
C15 C16 C17 C18 0.7(13) . . . . ?
N4 C16 C17 C18 -178.8(7) . . . . ?
C14 C13 C18 C17 0.0(12) . . . . ?
C14 C13 C18 C19 -179.2(7) . . . . ?
C16 C17 C18 C13 -0.9(12) . . . . ?
C16 C17 C18 C19 178.3(7) . . . . ?
C13 C18 C19 O2 -3.2(12) . . . . ?
C17 C18 C19 O2 177.6(9) . . . . ?
C13 C18 C19 O3 176.5(8) . . . . ?
C17 C18 C19 O3 -2.7(11) . . . . ?

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
O1 H1A N1 0.82 1.87 2.597(10) 147.4 .
O3 H3A N2 0.82 1.77 2.576(9) 167.3 .
C7 H7 O4 0.93 2.40 3.283(12) 157.6 2_645
C17 H17 Br1 0.93 3.03 3.923(9) 162.5 2_646

_refine_diff_density_max         0.682
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.097


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: THF'
_chemical_compound_source        photochromic
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC14
_database_code_depnum_ccdc_archive 'CCDC 1814065'
_audit_update_record             
;
2017-12-30 deposited with the CCDC.
2018-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
'4-bromo-2-[(E)-3-pyridyliminomethyl]phenol, 1,4-diiodobenzene'
_chemical_name_common            5Br3SAP-14IBz
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 Br N2 O, 0.5(C6 H4 I2)'
_chemical_formula_sum            'C15 H11 Br I N2 O'
_chemical_formula_weight         442.07

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   33.7985(6)
_cell_length_b                   6.91740(10)
_cell_length_c                   6.17460(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.7900(10)
_cell_angle_gamma                90
_cell_volume                     1441.90(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8412
_cell_measurement_theta_min      3.93
_cell_measurement_theta_max      68.19

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.036
_exptl_crystal_F_000             844
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.040
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    20.669
_shelx_estimated_absorpt_T_min   0.492
_shelx_estimated_absorpt_T_max   0.683
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.536
_exptl_absorpt_correction_T_max  0.683
_exptl_absorpt_process_details   'Absorption was corrected by ABSCOR'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating anode X-ray tube'
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID-II IP Area Detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12885
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.928
_diffrn_reflns_theta_max         68.224
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             2584
_reflns_number_gt                2406
_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       'PROCESS-AUTO (Rigaku, 1998)'
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'PROCESS-AUTO (Rigaku, 1998)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2008)'
_computing_publication_material  'SHELXL-2014/07 (Sheldrick, 2014)'
_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)+(0.0426P)²+0.5036P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2584
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0316
_refine_ls_wR_factor_ref         0.0786
_refine_ls_wR_factor_gt          0.0757
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_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
N2 N 0.16918(9) -0.0659(4) 0.5711(6) 0.0265(7) Uani 1 1 d . . . . .
C2 C 0.38861(11) 0.0712(5) 0.2739(7) 0.0223(8) Uani 1 1 d . . . . .
H2 H 0.391244 0.117677 0.130519 0.027 Uiso 1 1 calc R U . . .
O1 O 0.31912(8) 0.0702(4) 0.2126(5) 0.0293(6) Uani 1 1 d . . . . .
H1A H 0.298336 0.042295 0.275095 0.044 Uiso 1 1 d R U . . .
Br1 Br 0.46419(2) -0.06895(6) 0.79884(8) 0.02942(13) Uani 1 1 d . . . . .
N1 N 0.27644(8) -0.0195(4) 0.5355(5) 0.0210(7) Uani 1 1 d . . . . .
C1 C 0.35091(11) 0.0372(5) 0.3485(7) 0.0202(8) Uani 1 1 d . . . . .
C8 C 0.23923(10) -0.0135(5) 0.6314(6) 0.0192(7) Uani 1 1 d . . . . .
C12 C 0.23311(11) 0.0614(5) 0.8373(7) 0.0243(9) Uani 1 1 d . . . . .
H12 H 0.254771 0.106399 0.927450 0.029 Uiso 1 1 calc R U . . .
C11 C 0.19496(12) 0.0687(5) 0.9070(7) 0.0264(9) Uani 1 1 d . . . . .
H11 H 0.189953 0.117628 1.046836 0.032 Uiso 1 1 calc R U . . .
C3 C 0.42211(11) 0.0384(5) 0.4054(7) 0.0241(9) Uani 1 1 d . . . . .
H3 H 0.447623 0.062524 0.353130 0.029 Uiso 1 1 calc R U . . .
C10 C 0.16405(11) 0.0037(6) 0.7702(8) 0.0285(9) Uani 1 1 d . . . . .
H10 H 0.137929 0.008817 0.820162 0.034 Uiso 1 1 calc R U . . .
C4 C 0.41828(10) -0.0303(5) 0.6150(7) 0.0203(8) Uani 1 1 d . . . . .
C5 C 0.38124(10) -0.0660(5) 0.6942(6) 0.0189(8) Uani 1 1 d . . . . .
H5 H 0.379020 -0.114673 0.836934 0.023 Uiso 1 1 calc R U . . .
C6 C 0.34713(10) -0.0299(5) 0.5621(7) 0.0183(8) Uani 1 1 d . . . . .
C9 C 0.20622(11) -0.0720(5) 0.5049(7) 0.0229(8) Uani 1 1 d . . . . .
H9 H 0.210238 -0.119016 0.363113 0.028 Uiso 1 1 calc R U . . .
C7 C 0.30821(10) -0.0490(4) 0.6537(7) 0.0195(8) Uani 1 1 d . . . . .
H7 H 0.306412 -0.083399 0.801878 0.023 Uiso 1 1 calc R U . . .
I1 I 0.09117(2) -0.04187(3) 0.28707(4) 0.02404(11) Uani 1 1 d . . . . .
C14 C 0.03638(10) -0.0181(5) 0.1116(7) 0.0191(7) Uani 1 1 d . . . . .
C13 C 0.03431(11) 0.0549(5) -0.0985(7) 0.0223(9) Uani 1 1 d . . . . .
H13 H 0.057881 0.091501 -0.165572 0.027 Uiso 1 1 calc R U . . .
C15 C 0.00180(11) -0.0744(5) 0.2096(6) 0.0207(8) Uani 1 1 d . . . . .
H15 H 0.003188 -0.125984 0.352383 0.025 Uiso 1 1 calc 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
N2 C9 1.337(5) . ?
N2 C10 1.340(6) . ?
C2 C3 1.380(6) . ?
C2 C1 1.396(5) . ?
C2 H2 0.9500 . ?
O1 C1 1.350(5) . ?
O1 H1A 0.8401 . ?
Br1 C4 1.896(4) . ?
N1 C7 1.285(5) . ?
N1 C8 1.416(4) . ?
C1 C6 1.410(6) . ?
C8 C9 1.390(5) . ?
C8 C12 1.398(6) . ?
C12 C11 1.380(5) . ?
C12 H12 0.9500 . ?
C11 C10 1.386(6) . ?
C11 H11 0.9500 . ?
C3 C4 1.390(6) . ?
C3 H3 0.9500 . ?
C10 H10 0.9500 . ?
C4 C5 1.388(5) . ?
C5 C6 1.402(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.463(5) . ?
C9 H9 0.9500 . ?
C7 H7 0.9500 . ?
I1 C14 2.106(4) . ?
C14 C13 1.391(6) . ?
C14 C15 1.397(5) . ?
C13 C15 1.377(5) 3 ?
C13 H13 0.9500 . ?
C15 H15 0.9500 . ?

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
C9 N2 C10 117.2(3) . . ?
C3 C2 C1 121.0(4) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C1 O1 H1A 109.5 . . ?
C7 N1 C8 120.1(3) . . ?
O1 C1 C2 118.6(4) . . ?
O1 C1 C6 122.1(3) . . ?
C2 C1 C6 119.3(4) . . ?
C9 C8 C12 117.9(3) . . ?
C9 C8 N1 117.5(3) . . ?
C12 C8 N1 124.4(3) . . ?
C11 C12 C8 118.6(4) . . ?
C11 C12 H12 120.7 . . ?
C8 C12 H12 120.7 . . ?
C12 C11 C10 119.1(4) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C2 C3 C4 119.5(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
N2 C10 C11 123.3(4) . . ?
N2 C10 H10 118.4 . . ?
C11 C10 H10 118.4 . . ?
C5 C4 C3 121.0(3) . . ?
C5 C4 Br1 119.3(3) . . ?
C3 C4 Br1 119.7(3) . . ?
C4 C5 C6 119.6(4) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C1 119.6(3) . . ?
C5 C6 C7 119.2(4) . . ?
C1 C6 C7 121.0(3) . . ?
N2 C9 C8 123.9(4) . . ?
N2 C9 H9 118.1 . . ?
C8 C9 H9 118.1 . . ?
N1 C7 C6 120.5(4) . . ?
N1 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C13 C14 C15 120.0(3) . . ?
C13 C14 I1 120.7(3) . . ?
C15 C14 I1 119.3(3) . . ?
C15 C13 C14 120.2(3) 3 . ?
C15 C13 H13 119.9 3 . ?
C14 C13 H13 119.9 . . ?
C13 C15 C14 119.8(4) 3 . ?
C13 C15 H15 120.1 3 . ?
C14 C15 H15 120.1 . . ?

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
C3 C2 C1 O1 -179.5(3) . . . . ?
C3 C2 C1 C6 0.6(5) . . . . ?
C7 N1 C8 C9 -150.4(3) . . . . ?
C7 N1 C8 C12 35.0(5) . . . . ?
C9 C8 C12 C11 1.8(5) . . . . ?
N1 C8 C12 C11 176.4(3) . . . . ?
C8 C12 C11 C10 -0.7(5) . . . . ?
C1 C2 C3 C4 0.3(5) . . . . ?
C9 N2 C10 C11 0.2(6) . . . . ?
C12 C11 C10 N2 -0.3(6) . . . . ?
C2 C3 C4 C5 -0.1(5) . . . . ?
C2 C3 C4 Br1 -178.3(3) . . . . ?
C3 C4 C5 C6 -0.9(5) . . . . ?
Br1 C4 C5 C6 177.3(2) . . . . ?
C4 C5 C6 C1 1.7(5) . . . . ?
C4 C5 C6 C7 -173.8(3) . . . . ?
O1 C1 C6 C5 178.5(3) . . . . ?
C2 C1 C6 C5 -1.6(5) . . . . ?
O1 C1 C6 C7 -6.1(5) . . . . ?
C2 C1 C6 C7 173.9(3) . . . . ?
C10 N2 C9 C8 1.0(5) . . . . ?
C12 C8 C9 N2 -2.0(5) . . . . ?
N1 C8 C9 N2 -177.0(3) . . . . ?
C8 N1 C7 C6 -171.8(3) . . . . ?
C5 C6 C7 N1 -178.9(3) . . . . ?
C1 C6 C7 N1 5.6(5) . . . . ?
C15 C14 C13 C15 0.9(6) . . . 3 ?
I1 C14 C13 C15 -178.3(3) . . . 3 ?
C13 C14 C15 C13 -0.8(6) . . . 3 ?
I1 C14 C15 C13 178.3(3) . . . 3 ?

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
O1 H1A N1 0.84 1.85 2.592(4) 146.1 .

_refine_diff_density_max         2.339
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.153


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
_chemical_compound_source        non-photochromic
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC15
_database_code_depnum_ccdc_archive 'CCDC 1814050'
_audit_update_record             
;
2017-12-30 deposited with the CCDC.
2018-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
2,4-tert-butyl-6-[(E)-3-pyridyliminomethyl]phenol
_chemical_name_common            35tBu-3SAP
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H26 N2 O'
_chemical_formula_sum            'C20 H26 N2 O'
_chemical_formula_weight         310.43

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   6.1462(6)
_cell_length_b                   18.7572(19)
_cell_length_c                   16.1025(16)
_cell_angle_alpha                90
_cell_angle_beta                 95.859(2)
_cell_angle_gamma                90
_cell_volume                     1846.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    9871
_cell_measurement_theta_min      3.33
_cell_measurement_theta_max      27.45

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.117
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.069
_shelx_estimated_absorpt_T_min   0.990
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.196
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   'Absorption was corrected by ABSCOR'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode X-ray tube'
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID IP Area Detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17821
_diffrn_reflns_av_unetI/netI     0.0782
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.332
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             8298
_reflns_number_gt                3891
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.924
_reflns_Friedel_fraction_max     0.974
_reflns_Friedel_fraction_full    0.993

_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       'PROCESS-AUTO (Rigaku, 1998)'
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'PROCESS-AUTO (Rigaku, 1998)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2008)'
_computing_publication_material  'SHELXL-2014/07 (Sheldrick, 2014)'
_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)+(0.0678P)²+0.0432P] 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 x determined using 1276 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.5(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         8298
_refine_ls_number_parameters     491
_refine_ls_number_restraints     181
_refine_ls_R_factor_all          0.1515
_refine_ls_R_factor_gt           0.0686
_refine_ls_wR_factor_ref         0.1736
_refine_ls_wR_factor_gt          0.1397
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.036
_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
O1 O 1.2261(6) 0.46559(19) 0.4234(2) 0.0722(10) Uani 1 1 d . . . . .
H1A H 1.129380 0.443876 0.444248 0.108 Uiso 1 1 calc R U . . .
O2 O 0.4456(7) 0.55718(19) 0.8740(2) 0.0775(11) Uani 1 1 d . . . . .
H2A H 0.516045 0.564135 0.834135 0.116 Uiso 1 1 calc R U . . .
N1 N 0.9612(7) 0.3599(2) 0.4499(3) 0.0650(11) Uani 1 1 d . . . . .
N3 N 0.6807(7) 0.5231(2) 0.7546(3) 0.0666(11) Uani 1 1 d . . . . .
N4 N 0.9711(10) 0.6245(3) 0.6074(4) 0.1029(18) Uani 1 1 d . . . . .
C1 C 1.3106(9) 0.3130(3) 0.2907(3) 0.0667(14) Uani 1 1 d . . . . .
H1 H 1.259299 0.266606 0.282855 0.080 Uiso 1 1 calc R U . . .
C2 C 1.4654(9) 0.3377(3) 0.2420(3) 0.0635(13) Uani 1 1 d . . . . .
C3 C 1.5398(8) 0.4068(3) 0.2588(3) 0.0628(13) Uani 1 1 d . . . . .
H3 H 1.646401 0.424176 0.227077 0.075 Uiso 1 1 calc R U . . .
C4 C 1.4694(8) 0.4520(3) 0.3184(3) 0.0558(12) Uani 1 1 d . . . . .
C5 C 1.3057(8) 0.4247(3) 0.3652(3) 0.0576(13) Uani 1 1 d . . . . .
C6 C 1.2278(8) 0.3552(3) 0.3514(3) 0.0613(13) Uani 1 1 d . . . . .
C7 C 1.0570(9) 0.3253(3) 0.3970(3) 0.0705(15) Uani 1 1 d . . . . .
H7 H 1.016028 0.278180 0.386723 0.085 Uiso 1 1 calc R U . . .
C13 C 1.5552(8) 0.5283(3) 0.3299(3) 0.0618(13) Uani 1 1 d . . . . .
C14 C 1.3664(9) 0.5818(3) 0.3092(4) 0.0844(17) Uani 1 1 d . . . . .
H14A H 1.422659 0.629579 0.313450 0.127 Uiso 1 1 calc R U . . .
H14B H 1.258804 0.575655 0.347830 0.127 Uiso 1 1 calc R U . . .
H14C H 1.300283 0.573524 0.253405 0.127 Uiso 1 1 calc R U . . .
C15 C 1.6534(9) 0.5404(3) 0.4200(3) 0.0803(16) Uani 1 1 d . . . . .
H15A H 1.705209 0.588617 0.426275 0.120 Uiso 1 1 calc R U . . .
H15B H 1.773095 0.508103 0.433111 0.120 Uiso 1 1 calc R U . . .
H15C H 1.543552 0.532187 0.457255 0.120 Uiso 1 1 calc R U . . .
C16 C 1.7341(10) 0.5441(3) 0.2733(4) 0.0872(18) Uani 1 1 d . . . . .
H16A H 1.779236 0.592939 0.280209 0.131 Uiso 1 1 calc R U . . .
H16B H 1.678464 0.535971 0.216196 0.131 Uiso 1 1 calc R U . . .
H16C H 1.856911 0.513391 0.287921 0.131 Uiso 1 1 calc R U . . .
C17 C 1.5491(10) 0.2921(3) 0.1732(4) 0.0793(17) Uani 1 1 d . . . . .
C21 C 0.3488(8) 0.3726(3) 0.8075(3) 0.0592(13) Uani 1 1 d . . . . .
H21 H 0.399660 0.340341 0.770144 0.071 Uiso 1 1 calc R U . . .
C22 C 0.1870(8) 0.3518(3) 0.8554(3) 0.0554(12) Uani 1 1 d . . . . .
C23 C 0.1218(8) 0.4016(3) 0.9122(3) 0.0590(13) Uani 1 1 d . . . . .
H23 H 0.014821 0.387932 0.945889 0.071 Uiso 1 1 calc R U . . .
C24 C 0.2058(8) 0.4707(3) 0.9222(3) 0.0571(12) Uani 1 1 d . . . . .
C25 C 0.3643(8) 0.4900(3) 0.8701(3) 0.0568(12) Uani 1 1 d . . . . .
C26 C 0.4390(7) 0.4414(3) 0.8136(3) 0.0547(12) Uani 1 1 d . . . . .
C27 C 0.6019(8) 0.4599(3) 0.7580(3) 0.0621(13) Uani 1 1 d . . . . .
H27 H 0.651007 0.424762 0.723747 0.075 Uiso 1 1 calc R U . . .
C28 C 0.8376(9) 0.5372(3) 0.6988(3) 0.0654(14) Uani 1 1 d . . . . .
C29 C 0.8352(12) 0.6034(3) 0.6617(4) 0.092(2) Uani 1 1 d . . . . .
H29 H 0.730381 0.635781 0.675622 0.111 Uiso 1 1 calc R U . . .
C30 C 1.1238(11) 0.5770(4) 0.5899(4) 0.0888(19) Uani 1 1 d . . . . .
H30 H 1.221712 0.590287 0.552373 0.107 Uiso 1 1 calc R U . . .
C31 C 1.1433(9) 0.5107(3) 0.6239(3) 0.0770(17) Uani 1 1 d . . . . .
H31 H 1.251788 0.479711 0.609921 0.092 Uiso 1 1 calc R U . . .
C32 C 0.9986(8) 0.4905(3) 0.6797(3) 0.0713(15) Uani 1 1 d . . . . .
H32 H 1.009571 0.445576 0.704240 0.086 Uiso 1 1 calc R U . . .
C33 C 0.0866(9) 0.2767(3) 0.8456(3) 0.0633(13) Uani 1 1 d . . . . .
C34 C -0.0151(12) 0.2670(4) 0.7550(4) 0.107(2) Uani 1 1 d . . . . .
H34A H -0.067677 0.218995 0.747260 0.160 Uiso 1 1 calc R U . . .
H34B H 0.093476 0.276193 0.717555 0.160 Uiso 1 1 calc R U . . .
H34C H -0.134610 0.299670 0.743740 0.160 Uiso 1 1 calc R U . . .
C35 C -0.0905(11) 0.2648(3) 0.9048(4) 0.098(2) Uani 1 1 d . . . . .
H35A H -0.154464 0.218450 0.894992 0.147 Uiso 1 1 calc R U . . .
H35B H -0.201747 0.300580 0.894922 0.147 Uiso 1 1 calc R U . . .
H35C H -0.026159 0.267844 0.961589 0.147 Uiso 1 1 calc R U . . .
C36 C 0.2669(11) 0.2209(4) 0.8658(5) 0.098(2) Uani 1 1 d . . . . .
H36A H 0.203251 0.174089 0.863684 0.147 Uiso 1 1 calc R U . . .
H36B H 0.338354 0.229501 0.920719 0.147 Uiso 1 1 calc R U . . .
H36C H 0.371730 0.224151 0.825693 0.147 Uiso 1 1 calc R U . . .
C37 C 0.1289(9) 0.5230(3) 0.9863(3) 0.0666(14) Uani 1 1 d . . . . .
C38 C -0.0465(11) 0.4897(4) 1.0359(4) 0.103(2) Uani 1 1 d . . . . .
H38A H -0.092830 0.524151 1.074494 0.155 Uiso 1 1 calc R U . . .
H38B H 0.013436 0.448864 1.066024 0.155 Uiso 1 1 calc R U . . .
H38C H -0.169502 0.475330 0.998045 0.155 Uiso 1 1 calc R U . . .
C39 C 0.3229(10) 0.5454(4) 1.0481(4) 0.091(2) Uani 1 1 d . . . . .
H39A H 0.273133 0.577255 1.088827 0.137 Uiso 1 1 calc R U . . .
H39B H 0.430007 0.569116 1.018517 0.137 Uiso 1 1 calc R U . . .
H39C H 0.387195 0.503955 1.075609 0.137 Uiso 1 1 calc R U . . .
C40 C 0.0270(11) 0.5895(3) 0.9426(4) 0.0853(18) Uani 1 1 d . . . . .
H40A H -0.022943 0.621177 0.983402 0.128 Uiso 1 1 calc R U . . .
H40B H -0.094373 0.575609 0.903645 0.128 Uiso 1 1 calc R U . . .
H40C H 0.134631 0.613195 0.913305 0.128 Uiso 1 1 calc R U . . .
C18A C 1.413(4) 0.2263(9) 0.1498(14) 0.105(7) Uani 0.528(14) 1 d . U P A 1
H18A H 1.434252 0.212159 0.093943 0.157 Uiso 0.528(14) 1 calc R U P A 1
H18B H 1.261031 0.236928 0.152919 0.157 Uiso 0.528(14) 1 calc R U P A 1
H18C H 1.456917 0.188312 0.187737 0.157 Uiso 0.528(14) 1 calc R U P A 1
C19A C 1.498(3) 0.3381(7) 0.0844(7) 0.098(5) Uani 0.528(14) 1 d . U P A 1
H19A H 1.536349 0.309741 0.038498 0.148 Uiso 0.528(14) 1 calc R U P A 1
H19B H 1.583008 0.381158 0.087681 0.148 Uiso 0.528(14) 1 calc R U P A 1
H19C H 1.345307 0.349887 0.076102 0.148 Uiso 0.528(14) 1 calc R U P A 1
C20A C 1.784(3) 0.2822(13) 0.1828(13) 0.130(8) Uani 0.528(14) 1 d . U P A 1
H20A H 1.826766 0.254822 0.136760 0.196 Uiso 0.528(14) 1 calc R U P A 1
H20B H 1.826599 0.257376 0.234064 0.196 Uiso 0.528(14) 1 calc R U P A 1
H20C H 1.855240 0.327845 0.183976 0.196 Uiso 0.528(14) 1 calc R U P A 1
C18B C 1.367(4) 0.2610(16) 0.1230(16) 0.133(10) Uani 0.472(14) 1 d . U P A 2
H18D H 1.417891 0.223010 0.090145 0.200 Uiso 0.472(14) 1 calc R U P A 2
H18E H 1.297152 0.296732 0.086807 0.200 Uiso 0.472(14) 1 calc R U P A 2
H18F H 1.264112 0.242609 0.158636 0.200 Uiso 0.472(14) 1 calc R U P A 2
C19B C 1.728(4) 0.3256(11) 0.1332(13) 0.118(8) Uani 0.472(14) 1 d . U P A 2
H19D H 1.772692 0.294433 0.090792 0.177 Uiso 0.472(14) 1 calc R U P A 2
H19E H 1.849412 0.334271 0.174256 0.177 Uiso 0.472(14) 1 calc R U P A 2
H19F H 1.678187 0.369978 0.108243 0.177 Uiso 0.472(14) 1 calc R U P A 2
C20B C 1.684(3) 0.2236(10) 0.2264(9) 0.099(6) Uani 0.472(14) 1 d . U P A 2
H20D H 1.742802 0.191921 0.187449 0.149 Uiso 0.472(14) 1 calc R U P A 2
H20E H 1.584686 0.198029 0.257598 0.149 Uiso 0.472(14) 1 calc R U P A 2
H20F H 1.801707 0.242501 0.263951 0.149 Uiso 0.472(14) 1 calc R U P A 2
C8A C 0.806(2) 0.3305(7) 0.4929(8) 0.067(5) Uani 0.40(2) 1 d G U P B 3
C9A C 0.673(3) 0.3781(5) 0.5303(11) 0.068(5) Uani 0.40(2) 1 d G U P B 3
H9A H 0.699223 0.426845 0.527858 0.082 Uiso 0.40(2) 1 calc R U P B 3
N2A N 0.500(2) 0.3528(7) 0.5713(10) 0.074(5) Uani 0.40(2) 1 d G U P B 3
C10A C 0.461(2) 0.2800(7) 0.5749(7) 0.070(5) Uani 0.40(2) 1 d G U P B 3
H10A H 0.345068 0.263051 0.602308 0.083 Uiso 0.40(2) 1 calc R U P B 3
C11A C 0.594(3) 0.2324(6) 0.5375(11) 0.075(5) Uani 0.40(2) 1 d G U P B 3
H11A H 0.567793 0.183657 0.539901 0.090 Uiso 0.40(2) 1 calc R U P B 3
C12A C 0.767(3) 0.2577(7) 0.4965(10) 0.074(4) Uani 0.40(2) 1 d G U P B 3
H12A H 0.856236 0.225856 0.471472 0.088 Uiso 0.40(2) 1 calc R U P B 3
C8B C 0.7781(13) 0.3252(5) 0.4857(5) 0.057(3) Uani 0.60(2) 1 d G U P B 4
C9B C 0.7041(18) 0.3652(6) 0.5498(6) 0.068(3) Uani 0.60(2) 1 d G U P B 4
H9B H 0.771493 0.408166 0.565572 0.082 Uiso 0.60(2) 1 calc R U P B 4
N2B N 0.5294(18) 0.3409(6) 0.5905(6) 0.087(3) Uani 0.60(2) 1 d G U P B 4
C10B C 0.4287(13) 0.2766(6) 0.5670(5) 0.093(4) Uani 0.60(2) 1 d G U P B 4
H10B H 0.311792 0.260356 0.594155 0.112 Uiso 0.60(2) 1 calc R U P B 4
C11B C 0.5027(18) 0.2366(4) 0.5028(8) 0.077(3) Uani 0.60(2) 1 d G U P B 4
H11B H 0.435304 0.193609 0.487103 0.092 Uiso 0.60(2) 1 calc R U P B 4
C12B C 0.6774(18) 0.2609(4) 0.4622(7) 0.069(3) Uani 0.60(2) 1 d G U P B 4
H12B H 0.726911 0.234140 0.419285 0.083 Uiso 0.60(2) 1 calc R U P B 4


_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 C5 1.342(5) . ?
O1 H1A 0.8200 . ?
O2 C25 1.355(6) . ?
O2 H2A 0.8200 . ?
N1 C7 1.262(6) . ?
N1 C8A 1.350(11) . ?
N1 C8B 1.468(8) . ?
N3 C27 1.283(6) . ?
N3 C28 1.408(6) . ?
N4 C29 1.329(7) . ?
N4 C30 1.345(8) . ?
C1 C2 1.373(7) . ?
C1 C6 1.393(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.392(7) . ?
C2 C17 1.529(7) . ?
C3 C4 1.382(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.413(7) . ?
C4 C13 1.530(7) . ?
C5 C6 1.400(7) . ?
C6 C7 1.454(7) . ?
C7 H7 0.9300 . ?
C13 C16 1.527(7) . ?
C13 C15 1.531(7) . ?
C13 C14 1.545(7) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18B 1.44(3) . ?
C17 C20A 1.450(16) . ?
C17 C19B 1.471(17) . ?
C17 C18A 1.52(2) . ?
C17 C19A 1.672(14) . ?
C17 C20B 1.712(18) . ?
C21 C22 1.376(6) . ?
C21 C26 1.403(7) . ?
C21 H21 0.9300 . ?
C22 C23 1.395(7) . ?
C22 C33 1.540(7) . ?
C23 C24 1.397(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.398(6) . ?
C24 C37 1.533(7) . ?
C25 C26 1.398(6) . ?
C26 C27 1.451(6) . ?
C27 H27 0.9300 . ?
C28 C29 1.377(8) . ?
C28 C32 1.381(8) . ?
C29 H29 0.9300 . ?
C30 C31 1.359(9) . ?
C30 H30 0.9300 . ?
C31 C32 1.380(7) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C33 C36 1.534(8) . ?
C33 C35 1.535(8) . ?
C33 C34 1.538(8) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 C39 1.532(8) . ?
C37 C40 1.534(8) . ?
C37 C38 1.537(8) . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C18A H18A 0.9600 . ?
C18A H18B 0.9600 . ?
C18A H18C 0.9600 . ?
C19A H19A 0.9600 . ?
C19A H19B 0.9600 . ?
C19A H19C 0.9600 . ?
C20A H20A 0.9600 . ?
C20A H20B 0.9600 . ?
C20A H20C 0.9600 . ?
C18B H18D 0.9600 . ?
C18B H18E 0.9600 . ?
C18B H18F 0.9600 . ?
C19B H19D 0.9600 . ?
C19B H19E 0.9600 . ?
C19B H19F 0.9600 . ?
C20B H20D 0.9600 . ?
C20B H20E 0.9600 . ?
C20B H20F 0.9600 . ?
C8A C9A 1.3900 . ?
C8A C12A 1.3900 . ?
C9A N2A 1.3900 . ?
C9A H9A 0.9300 . ?
N2A C10A 1.3900 . ?
C10A C11A 1.3900 . ?
C10A H10A 0.9300 . ?
C11A C12A 1.3900 . ?
C11A H11A 0.9300 . ?
C12A H12A 0.9300 . ?
C8B C9B 1.3900 . ?
C8B C12B 1.3900 . ?
C9B N2B 1.3900 . ?
C9B H9B 0.9300 . ?
N2B C10B 1.3900 . ?
C10B C11B 1.3900 . ?
C10B H10B 0.9300 . ?
C11B C12B 1.3900 . ?
C11B H11B 0.9300 . ?
C12B H12B 0.9300 . ?

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
C5 O1 H1A 109.5 . . ?
C25 O2 H2A 109.5 . . ?
C7 N1 C8A 122.6(8) . . ?
C7 N1 C8B 117.8(6) . . ?
C27 N3 C28 119.2(5) . . ?
C29 N4 C30 116.0(6) . . ?
C2 C1 C6 122.2(5) . . ?
C2 C1 H1 118.9 . . ?
C6 C1 H1 118.9 . . ?
C1 C2 C3 115.9(5) . . ?
C1 C2 C17 121.9(5) . . ?
C3 C2 C17 122.2(5) . . ?
C4 C3 C2 125.9(5) . . ?
C4 C3 H3 117.1 . . ?
C2 C3 H3 117.1 . . ?
C3 C4 C5 116.0(5) . . ?
C3 C4 C13 122.0(4) . . ?
C5 C4 C13 122.0(4) . . ?
O1 C5 C6 120.0(4) . . ?
O1 C5 C4 119.7(5) . . ?
C6 C5 C4 120.3(4) . . ?
C1 C6 C5 119.8(4) . . ?
C1 C6 C7 118.1(5) . . ?
C5 C6 C7 122.1(5) . . ?
N1 C7 C6 123.7(5) . . ?
N1 C7 H7 118.2 . . ?
C6 C7 H7 118.2 . . ?
C16 C13 C4 111.7(4) . . ?
C16 C13 C15 107.4(4) . . ?
C4 C13 C15 110.6(4) . . ?
C16 C13 C14 108.4(5) . . ?
C4 C13 C14 109.9(4) . . ?
C15 C13 C14 108.9(4) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 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 . . ?
C18B C17 C19B 120.0(16) . . ?
C20A C17 C18A 116.2(13) . . ?
C18B C17 C2 109.5(11) . . ?
C20A C17 C2 113.6(8) . . ?
C19B C17 C2 113.6(8) . . ?
C18A C17 C2 114.6(9) . . ?
C20A C17 C19A 104.8(12) . . ?
C18A C17 C19A 99.0(11) . . ?
C2 C17 C19A 106.5(6) . . ?
C18B C17 C20B 106.7(13) . . ?
C19B C17 C20B 101.1(12) . . ?
C2 C17 C20B 103.9(6) . . ?
C22 C21 C26 121.7(5) . . ?
C22 C21 H21 119.2 . . ?
C26 C21 H21 119.2 . . ?
C21 C22 C23 116.7(5) . . ?
C21 C22 C33 120.5(4) . . ?
C23 C22 C33 122.8(4) . . ?
C22 C23 C24 124.7(5) . . ?
C22 C23 H23 117.7 . . ?
C24 C23 H23 117.7 . . ?
C23 C24 C25 116.3(4) . . ?
C23 C24 C37 122.3(4) . . ?
C25 C24 C37 121.4(4) . . ?
O2 C25 C24 119.3(4) . . ?
O2 C25 C26 119.5(4) . . ?
C24 C25 C26 121.2(4) . . ?
C25 C26 C21 119.4(4) . . ?
C25 C26 C27 122.5(5) . . ?
C21 C26 C27 118.0(4) . . ?
N3 C27 C26 122.4(5) . . ?
N3 C27 H27 118.8 . . ?
C26 C27 H27 118.8 . . ?
C29 C28 C32 116.8(5) . . ?
C29 C28 N3 118.0(5) . . ?
C32 C28 N3 125.1(5) . . ?
N4 C29 C28 125.1(6) . . ?
N4 C29 H29 117.4 . . ?
C28 C29 H29 117.4 . . ?
N4 C30 C31 123.9(6) . . ?
N4 C30 H30 118.1 . . ?
C31 C30 H30 118.1 . . ?
C30 C31 C32 118.5(6) . . ?
C30 C31 H31 120.7 . . ?
C32 C31 H31 120.7 . . ?
C31 C32 C28 119.6(5) . . ?
C31 C32 H32 120.2 . . ?
C28 C32 H32 120.2 . . ?
C36 C33 C35 108.1(5) . . ?
C36 C33 C34 109.6(5) . . ?
C35 C33 C34 109.1(5) . . ?
C36 C33 C22 109.2(5) . . ?
C35 C33 C22 111.8(4) . . ?
C34 C33 C22 109.0(4) . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C33 C35 H35A 109.5 . . ?
C33 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C33 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C33 C36 H36A 109.5 . . ?
C33 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C33 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C39 C37 C24 109.9(4) . . ?
C39 C37 C40 109.2(5) . . ?
C24 C37 C40 110.5(4) . . ?
C39 C37 C38 108.4(5) . . ?
C24 C37 C38 111.7(5) . . ?
C40 C37 C38 107.1(5) . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C37 C39 H39A 109.5 . . ?
C37 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C37 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C37 C40 H40A 109.5 . . ?
C37 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C37 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C17 C18A H18A 109.5 . . ?
C17 C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
C17 C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
C17 C19A H19A 109.5 . . ?
C17 C19A H19B 109.5 . . ?
H19A C19A H19B 109.5 . . ?
C17 C19A H19C 109.5 . . ?
H19A C19A H19C 109.5 . . ?
H19B C19A H19C 109.5 . . ?
C17 C20A H20A 109.5 . . ?
C17 C20A H20B 109.5 . . ?
H20A C20A H20B 109.5 . . ?
C17 C20A H20C 109.5 . . ?
H20A C20A H20C 109.5 . . ?
H20B C20A H20C 109.5 . . ?
C17 C18B H18D 109.5 . . ?
C17 C18B H18E 109.5 . . ?
H18D C18B H18E 109.5 . . ?
C17 C18B H18F 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?
C17 C19B H19D 109.5 . . ?
C17 C19B H19E 109.5 . . ?
H19D C19B H19E 109.5 . . ?
C17 C19B H19F 109.5 . . ?
H19D C19B H19F 109.5 . . ?
H19E C19B H19F 109.5 . . ?
C17 C20B H20D 109.5 . . ?
C17 C20B H20E 109.5 . . ?
H20D C20B H20E 109.5 . . ?
C17 C20B H20F 109.5 . . ?
H20D C20B H20F 109.5 . . ?
H20E C20B H20F 109.5 . . ?
N1 C8A C9A 116.0(10) . . ?
N1 C8A C12A 123.9(10) . . ?
C9A C8A C12A 120.0 . . ?
C8A C9A N2A 120.0 . . ?
C8A C9A H9A 120.0 . . ?
N2A C9A H9A 120.0 . . ?
C10A N2A C9A 120.0 . . ?
N2A C10A C11A 120.0 . . ?
N2A C10A H10A 120.0 . . ?
C11A C10A H10A 120.0 . . ?
C12A C11A C10A 120.0 . . ?
C12A C11A H11A 120.0 . . ?
C10A C11A H11A 120.0 . . ?
C11A C12A C8A 120.0 . . ?
C11A C12A H12A 120.0 . . ?
C8A C12A H12A 120.0 . . ?
C9B C8B C12B 120.0 . . ?
C9B C8B N1 112.0(6) . . ?
C12B C8B N1 128.0(6) . . ?
C8B C9B N2B 120.0 . . ?
C8B C9B H9B 120.0 . . ?
N2B C9B H9B 120.0 . . ?
C9B N2B C10B 120.0 . . ?
C11B C10B N2B 120.0 . . ?
C11B C10B H10B 120.0 . . ?
N2B C10B H10B 120.0 . . ?
C12B C11B C10B 120.0 . . ?
C12B C11B H11B 120.0 . . ?
C10B C11B H11B 120.0 . . ?
C11B C12B C8B 120.0 . . ?
C11B C12B H12B 120.0 . . ?
C8B C12B H12B 120.0 . . ?

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 1.9(8) . . . . ?
C6 C1 C2 C17 -177.6(5) . . . . ?
C1 C2 C3 C4 -1.0(8) . . . . ?
C17 C2 C3 C4 178.5(5) . . . . ?
C2 C3 C4 C5 -0.7(8) . . . . ?
C2 C3 C4 C13 -177.6(5) . . . . ?
C3 C4 C5 O1 -179.0(5) . . . . ?
C13 C4 C5 O1 -2.1(7) . . . . ?
C3 C4 C5 C6 1.5(7) . . . . ?
C13 C4 C5 C6 178.5(4) . . . . ?
C2 C1 C6 C5 -1.1(8) . . . . ?
C2 C1 C6 C7 177.2(5) . . . . ?
O1 C5 C6 C1 179.9(5) . . . . ?
C4 C5 C6 C1 -0.7(7) . . . . ?
O1 C5 C6 C7 1.6(7) . . . . ?
C4 C5 C6 C7 -179.0(5) . . . . ?
C8A N1 C7 C6 -178.5(8) . . . . ?
C8B N1 C7 C6 174.5(6) . . . . ?
C1 C6 C7 N1 -175.8(5) . . . . ?
C5 C6 C7 N1 2.5(8) . . . . ?
C3 C4 C13 C16 -4.3(7) . . . . ?
C5 C4 C13 C16 178.9(5) . . . . ?
C3 C4 C13 C15 -123.8(5) . . . . ?
C5 C4 C13 C15 59.4(6) . . . . ?
C3 C4 C13 C14 116.0(5) . . . . ?
C5 C4 C13 C14 -60.8(6) . . . . ?
C1 C2 C17 C18B 47.7(16) . . . . ?
C3 C2 C17 C18B -131.8(15) . . . . ?
C1 C2 C17 C20A -123.2(14) . . . . ?
C3 C2 C17 C20A 57.4(15) . . . . ?
C1 C2 C17 C19B -175.0(13) . . . . ?
C3 C2 C17 C19B 5.6(14) . . . . ?
C1 C2 C17 C18A 13.6(13) . . . . ?
C3 C2 C17 C18A -165.8(11) . . . . ?
C1 C2 C17 C19A 122.0(8) . . . . ?
C3 C2 C17 C19A -57.5(9) . . . . ?
C1 C2 C17 C20B -66.0(9) . . . . ?
C3 C2 C17 C20B 114.5(8) . . . . ?
C26 C21 C22 C23 -2.0(7) . . . . ?
C26 C21 C22 C33 178.3(5) . . . . ?
C21 C22 C23 C24 1.4(7) . . . . ?
C33 C22 C23 C24 -178.9(5) . . . . ?
C22 C23 C24 C25 0.8(7) . . . . ?
C22 C23 C24 C37 -179.5(5) . . . . ?
C23 C24 C25 O2 177.1(5) . . . . ?
C37 C24 C25 O2 -2.6(7) . . . . ?
C23 C24 C25 C26 -2.3(7) . . . . ?
C37 C24 C25 C26 177.9(5) . . . . ?
O2 C25 C26 C21 -177.7(5) . . . . ?
C24 C25 C26 C21 1.8(7) . . . . ?
O2 C25 C26 C27 -0.1(7) . . . . ?
C24 C25 C26 C27 179.4(4) . . . . ?
C22 C21 C26 C25 0.5(7) . . . . ?
C22 C21 C26 C27 -177.3(5) . . . . ?
C28 N3 C27 C26 -179.7(5) . . . . ?
C25 C26 C27 N3 -3.2(7) . . . . ?
C21 C26 C27 N3 174.4(5) . . . . ?
C27 N3 C28 C29 145.4(6) . . . . ?
C27 N3 C28 C32 -36.3(7) . . . . ?
C30 N4 C29 C28 -1.4(10) . . . . ?
C32 C28 C29 N4 2.1(10) . . . . ?
N3 C28 C29 N4 -179.5(6) . . . . ?
C29 N4 C30 C31 0.2(10) . . . . ?
N4 C30 C31 C32 0.1(10) . . . . ?
C30 C31 C32 C28 0.7(8) . . . . ?
C29 C28 C32 C31 -1.6(8) . . . . ?
N3 C28 C32 C31 -179.9(5) . . . . ?
C21 C22 C33 C36 60.4(6) . . . . ?
C23 C22 C33 C36 -119.3(5) . . . . ?
C21 C22 C33 C35 -179.9(5) . . . . ?
C23 C22 C33 C35 0.3(7) . . . . ?
C21 C22 C33 C34 -59.3(6) . . . . ?
C23 C22 C33 C34 120.9(6) . . . . ?
C23 C24 C37 C39 120.4(5) . . . . ?
C25 C24 C37 C39 -59.9(6) . . . . ?
C23 C24 C37 C40 -119.1(5) . . . . ?
C25 C24 C37 C40 60.6(6) . . . . ?
C23 C24 C37 C38 0.0(7) . . . . ?
C25 C24 C37 C38 179.7(5) . . . . ?
C7 N1 C8A C9A -162.4(8) . . . . ?
C7 N1 C8A C12A 13.3(13) . . . . ?
N1 C8A C9A N2A 175.9(10) . . . . ?
C12A C8A C9A N2A 0.0 . . . . ?
C8A C9A N2A C10A 0.0 . . . . ?
C9A N2A C10A C11A 0.0 . . . . ?
N2A C10A C11A C12A 0.0 . . . . ?
C10A C11A C12A C8A 0.0 . . . . ?
N1 C8A C12A C11A -175.5(11) . . . . ?
C9A C8A C12A C11A 0.0 . . . . ?
C7 N1 C8B C9B 172.9(6) . . . . ?
C7 N1 C8B C12B -8.0(9) . . . . ?
C12B C8B C9B N2B 0.0 . . . . ?
N1 C8B C9B N2B 179.2(6) . . . . ?
C8B C9B N2B C10B 0.0 . . . . ?
C9B N2B C10B C11B 0.0 . . . . ?
N2B C10B C11B C12B 0.0 . . . . ?
C10B C11B C12B C8B 0.0 . . . . ?
C9B C8B C12B C11B 0.0 . . . . ?
N1 C8B C12B C11B -179.1(7) . . . . ?

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
O1 H1A N1 0.82 1.89 2.628(6) 148.9 .
O2 H2A N3 0.82 1.88 2.600(5) 146.4 .
C12A H12A N4 0.93 2.57 3.490(12) 168.2 2_746

_refine_diff_density_max         0.179
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.031


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
_chemical_compound_source        photochromic
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC16
_database_code_depnum_ccdc_archive 'CCDC 1814067'
_audit_update_record             
;
2017-12-30 deposited with the CCDC.
2018-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
'4-bromo-2-[(E)-3-pyridyliminomethyl]phenol, 1,3-diiodobenzene'
_chemical_name_common            5Br3SAP-13IBz
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H11 Br I N2 O'
_chemical_formula_sum            'C15 H11 Br I N2 O'
_chemical_formula_weight         442.07

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'
Br Br -0.2183 2.4073 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4615 1.7913 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0064 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_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, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   6.1651(12)
_cell_length_b                   66.924(13)
_cell_length_c                   6.8330(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2819.2(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    8887
_cell_measurement_theta_min      0.9
_cell_measurement_theta_max      27.11

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.083
_exptl_crystal_F_000             1688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    4.878
_shelx_estimated_absorpt_T_min   0.592
_shelx_estimated_absorpt_T_max   0.867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.419
_exptl_absorpt_correction_T_max  0.867
_exptl_absorpt_process_details   'Absorption was corrected by ABSCOR'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.6998
_diffrn_radiation_type           ?
_diffrn_source                   synchrotron
_diffrn_measurement_device_type  Rigaku
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16830
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -83
_diffrn_reflns_limit_k_max       83
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.198
_diffrn_reflns_theta_max         27.026
_diffrn_reflns_theta_full        24.827
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3207
_reflns_number_gt                2960
_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       'PROCESS-AUTO (Rigaku, 1998)'
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'PROCESS-AUTO (Rigaku, 1998)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2008)'
_computing_publication_material  'SHELXL-2014/07 (Sheldrick, 2014)'
_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)+(0.0491P)²+1.3399P] 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_number_reflns         3207
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0294
_refine_ls_wR_factor_ref         0.0797
_refine_ls_wR_factor_gt          0.0768
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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
I1 I 0.40721(3) 0.20515(2) 0.44999(2) 0.01207(8) Uani 1 1 d . . . . .
Br1 Br 0.80819(4) 0.01774(2) 0.43071(3) 0.01623(9) Uani 1 1 d . . . . .
O1 O 0.2665(3) 0.09102(3) 0.5695(2) 0.0163(4) Uani 1 1 d . . . . .
H1 H 0.338971 0.101411 0.547897 0.024 Uiso 1 1 calc R U . . .
N1 N 0.6025(3) 0.11227(3) 0.4799(3) 0.0108(4) Uani 1 1 d . . . . .
N2 N 0.6722(4) 0.16615(3) 0.4340(3) 0.0155(5) Uani 1 1 d . . . . .
C1 C 0.6384(4) 0.04094(4) 0.4690(4) 0.0129(5) Uani 1 1 d . . . . .
C2 C 0.4273(4) 0.03907(4) 0.5388(3) 0.0125(5) Uani 1 1 d . . . . .
H2 H 0.367591 0.026229 0.563526 0.015 Uiso 1 1 calc R U . . .
C3 C 0.3046(4) 0.05616(4) 0.5718(3) 0.0137(5) Uani 1 1 d . . . . .
H3 H 0.160409 0.054977 0.619560 0.016 Uiso 1 1 calc R U . . .
C4 C 0.3907(4) 0.07485(4) 0.5358(3) 0.0108(5) Uani 1 1 d . . . . .
C5 C 0.6059(4) 0.07678(4) 0.4689(3) 0.0096(5) Uani 1 1 d . . . . .
C6 C 0.7280(4) 0.05940(4) 0.4344(3) 0.0108(5) Uani 1 1 d . . . . .
H6 H 0.872520 0.060423 0.387126 0.013 Uiso 1 1 calc R U . . .
C7 C 0.7106(4) 0.09604(4) 0.4499(3) 0.0119(5) Uani 1 1 d . . . . .
H7 H 0.859594 0.096739 0.415225 0.014 Uiso 1 1 calc R U . . .
C8 C 0.7092(4) 0.13085(4) 0.4863(4) 0.0106(4) Uani 1 1 d . . . . .
C9 C 0.5928(4) 0.14768(4) 0.4268(3) 0.0129(5) Uani 1 1 d . . . . .
H9 H 0.449640 0.145856 0.378671 0.016 Uiso 1 1 calc R U . . .
C10 C 0.8724(4) 0.16851(4) 0.5046(4) 0.0162(5) Uani 1 1 d . . . . .
H10 H 0.930970 0.181633 0.510087 0.019 Uiso 1 1 calc R U . . .
C11 C 0.9987(4) 0.15283(4) 0.5701(3) 0.0153(5) Uani 1 1 d . . . . .
H11 H 1.140102 0.155223 0.620274 0.018 Uiso 1 1 calc R U . . .
C12 C 0.9167(4) 0.13355(4) 0.5618(3) 0.0133(5) Uani 1 1 d . . . . .
H12 H 0.999840 0.122503 0.606376 0.016 Uiso 1 1 calc R U . . .
C15 C 0.0236(4) 0.23200(4) 0.5449(3) 0.0117(5) Uani 1 1 d . . . . .
H15 H -0.048934 0.219709 0.568641 0.014 Uiso 1 1 calc R U . . .
C13 C 0.3441(6) 0.250000 0.4396(4) 0.0104(7) Uani 1 2 d S T P . .
H13 H 0.487185 0.250000 0.388007 0.012 Uiso 1 2 calc R U P . .
C16 C -0.0801(5) 0.250000 0.5759(5) 0.0122(7) Uani 1 2 d S T P . .
H16 H -0.226441 0.250000 0.619566 0.015 Uiso 1 2 calc R U P . .
C14 C 0.2381(4) 0.23225(4) 0.4778(3) 0.0108(5) 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
I1 C14 2.100(2) . ?
Br1 C1 1.891(3) . ?
O1 C4 1.345(3) . ?
O1 H1 0.8400 . ?
N1 C7 1.290(3) . ?
N1 C8 1.407(3) . ?
N2 C9 1.330(4) . ?
N2 C10 1.335(4) . ?
C1 C6 1.374(4) . ?
C1 C2 1.392(4) . ?
C2 C3 1.390(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.381(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.409(3) . ?
C5 C6 1.405(4) . ?
C5 C7 1.447(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C12 1.391(3) . ?
C8 C9 1.396(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.381(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.387(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C15 C16 1.381(3) . ?
C15 C14 1.400(3) . ?
C15 H15 0.9500 . ?
C13 C14 1.381(3) . ?
C13 C14 1.381(3) 8_565 ?
C13 H13 0.9500 . ?
C16 H16 0.9500 . ?

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
C4 O1 H1 109.5 . . ?
C7 N1 C8 120.5(2) . . ?
C9 N2 C10 117.6(2) . . ?
C6 C1 C2 121.1(2) . . ?
C6 C1 Br1 119.5(2) . . ?
C2 C1 Br1 119.4(2) . . ?
C3 C2 C1 119.4(2) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C4 C3 C2 120.5(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
O1 C4 C3 118.6(2) . . ?
O1 C4 C5 121.2(2) . . ?
C3 C4 C5 120.2(2) . . ?
C6 C5 C4 118.9(2) . . ?
C6 C5 C7 118.9(2) . . ?
C4 C5 C7 122.0(2) . . ?
C1 C6 C5 120.0(2) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
N1 C7 C5 120.3(2) . . ?
N1 C7 H7 119.8 . . ?
C5 C7 H7 119.8 . . ?
C12 C8 C9 118.4(2) . . ?
C12 C8 N1 123.8(2) . . ?
C9 C8 N1 117.6(2) . . ?
N2 C9 C8 123.4(2) . . ?
N2 C9 H9 118.3 . . ?
C8 C9 H9 118.3 . . ?
N2 C10 C11 123.3(3) . . ?
N2 C10 H10 118.4 . . ?
C11 C10 H10 118.4 . . ?
C10 C11 C12 119.2(2) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C11 C12 C8 118.1(3) . . ?
C11 C12 H12 120.9 . . ?
C8 C12 H12 120.9 . . ?
C16 C15 C14 118.5(2) . . ?
C16 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
C14 C13 C14 118.8(3) . 8_565 ?
C14 C13 H13 120.6 . . ?
C14 C13 H13 120.6 8_565 . ?
C15 C16 C15 121.6(3) . 8_565 ?
C15 C16 H16 119.2 . . ?
C15 C16 H16 119.2 8_565 . ?
C13 C14 C15 121.3(2) . . ?
C13 C14 I1 119.4(2) . . ?
C15 C14 I1 119.21(18) . . ?

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 0.7(3) . . . . ?
Br1 C1 C2 C3 178.29(17) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C2 C3 C4 O1 179.9(2) . . . . ?
C2 C3 C4 C5 -1.3(3) . . . . ?
O1 C4 C5 C6 -179.4(2) . . . . ?
C3 C4 C5 C6 1.8(3) . . . . ?
O1 C4 C5 C7 5.7(4) . . . . ?
C3 C4 C5 C7 -173.0(2) . . . . ?
C2 C1 C6 C5 -0.2(4) . . . . ?
Br1 C1 C6 C5 -177.77(17) . . . . ?
C4 C5 C6 C1 -1.1(3) . . . . ?
C7 C5 C6 C1 174.0(2) . . . . ?
C8 N1 C7 C5 171.8(2) . . . . ?
C6 C5 C7 N1 179.7(2) . . . . ?
C4 C5 C7 N1 -5.4(4) . . . . ?
C7 N1 C8 C12 -34.7(4) . . . . ?
C7 N1 C8 C9 150.3(2) . . . . ?
C10 N2 C9 C8 -0.9(4) . . . . ?
C12 C8 C9 N2 1.7(4) . . . . ?
N1 C8 C9 N2 177.0(2) . . . . ?
C9 N2 C10 C11 -0.2(4) . . . . ?
N2 C10 C11 C12 0.5(4) . . . . ?
C10 C11 C12 C8 0.3(3) . . . . ?
C9 C8 C12 C11 -1.3(3) . . . . ?
N1 C8 C12 C11 -176.3(2) . . . . ?
C14 C15 C16 C15 -0.9(5) . . . 8_565 ?
C14 C13 C14 C15 3.1(5) 8_565 . . . ?
C14 C13 C14 I1 -173.40(15) 8_565 . . . ?
C16 C15 C14 C13 -1.1(4) . . . . ?
C16 C15 C14 I1 175.4(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
O1 H1 N1 0.84 1.84 2.586(3) 147.3 .

_refine_diff_density_max         1.047
_refine_diff_density_min         -1.626
_refine_diff_density_rms         0.297


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
_chemical_compound_source        non-photochromic
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC17
_database_code_depnum_ccdc_archive 'CCDC 1814058'
_audit_update_record             
;
2017-12-30 deposited with the CCDC.
2018-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
'4-bromo-2-[(E)-3-pyridyliminomethyl]phenol/2hydroxybenzoic acid'
_chemical_name_common            5Br3SAP-2OHBA
_chemical_melting_point          ?
_chemical_formula_moiety         '(C12 H9 Br N2 O1),(C7 H6 O3)'
_chemical_formula_sum            'C19 H15 Br N2 O4'
_chemical_formula_weight         415.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'

_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                   3.82640(10)
_cell_length_b                   20.7111(7)
_cell_length_c                   21.2587(8)
_cell_angle_alpha                90
_cell_angle_beta                 93.890(2)
_cell_angle_gamma                90
_cell_volume                     1680.85(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    15638
_cell_measurement_theta_min      2.982
_cell_measurement_theta_max      68.235

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.109
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.032
_exptl_absorpt_coefficient_mu    3.589
_shelx_estimated_absorpt_T_min   0.696
_shelx_estimated_absorpt_T_max   0.894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8645
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   abscore,T.Higashi,RIGAKU
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating anode x-ray'
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID2'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            15638
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.982
_diffrn_reflns_theta_max         68.235
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3090
_reflns_number_gt                2808
_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       RAPID-AUTO
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        RAPID-AUTO
_computing_structure_solution    'SHELXS-97(Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
; 
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. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0394P)²+0.7736P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3090
_refine_ls_number_parameters     242
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0312
_refine_ls_wR_factor_ref         0.0834
_refine_ls_wR_factor_gt          0.0809
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_refine_ls_shift/su_max          0.003
_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
Br1 Br 1.21983(6) 0.82950(2) 0.10755(2) 0.03509(11) Uani 1 1 d . . . . .
H1 H 1.181(6) 0.5836(11) 0.1746(11) 0.030(6) Uiso 1 1 d . . . . .
O1 O 0.7170(4) 0.57021(7) 0.00844(7) 0.0334(4) Uani 1 1 d . . . . .
H1A H 0.764886 0.540632 0.034661 0.050 Uiso 1 1 calc R U . . .
C1 C 0.8342(5) 0.62743(10) 0.03270(9) 0.0252(4) Uani 1 1 d . . . . .
C8 C 1.0335(5) 0.46595(10) 0.15608(9) 0.0229(4) Uani 1 1 d . . . . .
C7 C 1.0606(5) 0.57684(10) 0.13416(9) 0.0247(4) Uani 1 1 d . . . . .
C6 C 0.9978(5) 0.63275(10) 0.09407(9) 0.0228(4) Uani 1 1 d . . . . .
C5 C 1.1078(5) 0.69373(10) 0.11635(9) 0.0249(4) Uani 1 1 d . . . . .
H5 H 1.214164 0.698157 0.157814 0.030 Uiso 1 1 calc R U . . .
N1 N 0.9655(4) 0.51988(8) 0.11637(8) 0.0245(4) Uani 1 1 d . . . . .
N3 N 0.9462(5) 0.35185(9) 0.16636(9) 0.0301(4) Uani 1 1 d . . . . .
C3 C 0.9047(5) 0.74145(10) 0.01753(10) 0.0279(5) Uani 1 1 d . . . . .
H3 H 0.876946 0.778580 -0.008569 0.034 Uiso 1 1 calc R U . . .
C10 C 1.1161(6) 0.35342(11) 0.22356(10) 0.0305(5) Uani 1 1 d . . . . .
H10 H 1.141667 0.314624 0.247270 0.037 Uiso 1 1 calc R U . . .
C9 C 0.9063(5) 0.40685(10) 0.13340(10) 0.0273(4) Uani 1 1 d . . . . .
H9 H 0.786002 0.405405 0.092836 0.033 Uiso 1 1 calc R U . . .
C11 C 1.2546(6) 0.40984(11) 0.24884(10) 0.0302(5) Uani 1 1 d . . . . .
H11 H 1.374907 0.409668 0.289429 0.036 Uiso 1 1 calc R U . . .
C13 C 0.5983(5) 0.20253(10) 0.16279(10) 0.0264(4) Uani 1 1 d . . . . .
C12 C 1.2181(5) 0.46675(10) 0.21500(10) 0.0269(4) Uani 1 1 d . . . . .
H12 H 1.317056 0.505756 0.231596 0.032 Uiso 1 1 calc R U . . .
C15 C 0.5006(5) 0.12575(10) 0.07200(9) 0.0256(4) Uani 1 1 d . . . . .
H15 H 0.601692 0.156565 0.045553 0.031 Uiso 1 1 calc R U . . .
C14 C 0.4759(5) 0.13980(9) 0.13588(9) 0.0229(4) Uani 1 1 d . . . . .
C16 C 0.3805(6) 0.06783(11) 0.04678(10) 0.0312(5) Uani 1 1 d . . . . .
H16 H 0.395131 0.059110 0.003168 0.037 Uiso 1 1 calc R U . . .
C17 C 0.2375(6) 0.02222(11) 0.08584(11) 0.0323(5) Uani 1 1 d . . . . .
H17 H 0.154581 -0.017738 0.068701 0.039 Uiso 1 1 calc R U . . .
C18 C 0.2154(6) 0.03463(10) 0.14912(11) 0.0305(5) Uani 1 1 d . . . . .
H18 H 0.121928 0.002908 0.175559 0.037 Uiso 1 1 calc R U . . .
C19 C 0.3299(5) 0.09366(10) 0.17444(9) 0.0260(4) Uani 1 1 d . . . . .
C2 C 0.7897(6) 0.68226(11) -0.00471(10) 0.0289(5) Uani 1 1 d . . . . .
H2 H 0.679044 0.678822 -0.045950 0.035 Uiso 1 1 calc R U . . .
O2 O 0.5787(4) 0.21539(7) 0.21917(7) 0.0353(4) Uani 1 1 d . . . . .
O3 O 0.7266(4) 0.24205(7) 0.12231(7) 0.0340(4) Uani 1 1 d . . . . .
H3A H 0.790850 0.276342 0.140754 0.051 Uiso 1 1 calc R U . . .
C4 C 1.0617(5) 0.74694(10) 0.07828(10) 0.0252(4) Uani 1 1 d . . . . .
O4 O 0.2962(5) 0.10464(8) 0.23692(7) 0.0360(4) Uani 1 1 d . . . . .
H4 H 0.361317 0.142443 0.245991 0.054 Uiso 1 1 calc 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
Br1 C4 1.904(2) . ?
O1 C1 1.357(2) . ?
O1 H1A 0.8400 . ?
C1 C2 1.390(3) . ?
C1 C6 1.413(3) . ?
C8 C9 1.391(3) . ?
C8 C12 1.396(3) . ?
C8 N1 1.414(3) . ?
C7 N1 1.284(3) . ?
C7 C6 1.448(3) . ?
C7 H1 0.96(2) . ?
C6 C5 1.403(3) . ?
C5 C4 1.372(3) . ?
C5 H5 0.9500 . ?
N3 C10 1.340(3) . ?
N3 C9 1.341(3) . ?
C3 C2 1.375(3) . ?
C3 C4 1.392(3) . ?
C3 H3 0.9500 . ?
C10 C11 1.377(3) . ?
C10 H10 0.9500 . ?
C9 H9 0.9500 . ?
C11 C12 1.383(3) . ?
C11 H11 0.9500 . ?
C13 O2 1.235(2) . ?
C13 O3 1.307(3) . ?
C13 C14 1.483(3) . ?
C12 H12 0.9500 . ?
C15 C16 1.380(3) . ?
C15 C14 1.398(3) . ?
C15 H15 0.9500 . ?
C14 C19 1.400(3) . ?
C16 C17 1.394(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.378(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.394(3) . ?
C18 H18 0.9500 . ?
C19 O4 1.362(3) . ?
C2 H2 0.9500 . ?
O3 H3A 0.8400 . ?
O4 H4 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1A 109.5 . . ?
O1 C1 C2 118.14(18) . . ?
O1 C1 C6 122.24(18) . . ?
C2 C1 C6 119.62(19) . . ?
C9 C8 C12 117.72(19) . . ?
C9 C8 N1 116.25(17) . . ?
C12 C8 N1 126.02(18) . . ?
N1 C7 C6 121.92(18) . . ?
N1 C7 H1 120.6(14) . . ?
C6 C7 H1 117.5(14) . . ?
C5 C6 C1 119.06(18) . . ?
C5 C6 C7 119.15(18) . . ?
C1 C6 C7 121.79(18) . . ?
C4 C5 C6 120.03(18) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C7 N1 C8 120.86(17) . . ?
C10 N3 C9 119.01(18) . . ?
C2 C3 C4 119.99(19) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
N3 C10 C11 121.7(2) . . ?
N3 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
N3 C9 C8 122.79(19) . . ?
N3 C9 H9 118.6 . . ?
C8 C9 H9 118.6 . . ?
C10 C11 C12 119.83(19) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
O2 C13 O3 123.65(19) . . ?
O2 C13 C14 121.67(19) . . ?
O3 C13 C14 114.68(18) . . ?
C11 C12 C8 118.94(19) . . ?
C11 C12 H12 120.5 . . ?
C8 C12 H12 120.5 . . ?
C16 C15 C14 121.0(2) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C14 C19 118.87(18) . . ?
C15 C14 C13 121.11(18) . . ?
C19 C14 C13 120.02(18) . . ?
C15 C16 C17 119.4(2) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C18 C17 C16 120.5(2) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 120.1(2) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
O4 C19 C18 118.34(19) . . ?
O4 C19 C14 121.67(19) . . ?
C18 C19 C14 120.00(19) . . ?
C3 C2 C1 120.49(19) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C13 O3 H3A 109.5 . . ?
C5 C4 C3 120.80(19) . . ?
C5 C4 Br1 120.23(15) . . ?
C3 C4 Br1 118.96(15) . . ?
C19 O4 H4 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
O1 C1 C6 C5 -179.07(19) . . . . ?
C2 C1 C6 C5 0.9(3) . . . . ?
O1 C1 C6 C7 2.0(3) . . . . ?
C2 C1 C6 C7 -178.0(2) . . . . ?
N1 C7 C6 C5 179.88(19) . . . . ?
N1 C7 C6 C1 -1.2(3) . . . . ?
C1 C6 C5 C4 -1.2(3) . . . . ?
C7 C6 C5 C4 177.73(19) . . . . ?
C6 C7 N1 C8 179.24(18) . . . . ?
C9 C8 N1 C7 177.34(19) . . . . ?
C12 C8 N1 C7 -3.4(3) . . . . ?
C9 N3 C10 C11 -0.9(3) . . . . ?
C10 N3 C9 C8 -0.1(3) . . . . ?
C12 C8 C9 N3 1.8(3) . . . . ?
N1 C8 C9 N3 -178.88(19) . . . . ?
N3 C10 C11 C12 0.3(3) . . . . ?
C10 C11 C12 C8 1.4(3) . . . . ?
C9 C8 C12 C11 -2.4(3) . . . . ?
N1 C8 C12 C11 178.38(19) . . . . ?
C16 C15 C14 C19 0.7(3) . . . . ?
C16 C15 C14 C13 -178.76(19) . . . . ?
O2 C13 C14 C15 -179.78(19) . . . . ?
O3 C13 C14 C15 0.1(3) . . . . ?
O2 C13 C14 C19 0.8(3) . . . . ?
O3 C13 C14 C19 -179.34(18) . . . . ?
C14 C15 C16 C17 -1.0(3) . . . . ?
C15 C16 C17 C18 0.0(3) . . . . ?
C16 C17 C18 C19 1.3(3) . . . . ?
C17 C18 C19 O4 178.52(19) . . . . ?
C17 C18 C19 C14 -1.6(3) . . . . ?
C15 C14 C19 O4 -179.52(18) . . . . ?
C13 C14 C19 O4 -0.1(3) . . . . ?
C15 C14 C19 C18 0.7(3) . . . . ?
C13 C14 C19 C18 -179.89(19) . . . . ?
C4 C3 C2 C1 -1.1(3) . . . . ?
O1 C1 C2 C3 -179.8(2) . . . . ?
C6 C1 C2 C3 0.2(3) . . . . ?
C6 C5 C4 C3 0.3(3) . . . . ?
C6 C5 C4 Br1 -178.58(15) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
C2 C3 C4 Br1 179.74(16) . . . . ?

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
O1 H1A N1 0.84 1.90 2.638(2) 145.9 .
C11 H11 Br1 0.95 3.08 3.912(2) 146.8 2_845
C12 H12 O4 0.95 2.59 3.521(3) 167.3 2_755
O3 H3A N3 0.84 1.75 2.578(2) 170.1 .
O4 H4 O2 0.84 1.83 2.574(2) 146.1 .

_refine_diff_density_max         0.482
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.074


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
_chemical_compound_source        non-photochromic
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC18
_database_code_depnum_ccdc_archive 'CCDC 1814048'
_audit_update_record             
;
2017-12-30 deposited with the CCDC.
2018-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        3-ethoxy-6-[(E)-3-pyridyliminomethyl]phenol
_chemical_name_common            3OEt-3SAP
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H14 N2 O2'
_chemical_formula_sum            'C14 H14 N2 O2'
_chemical_formula_weight         242.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'

_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'
'-x+1/4, y+1/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+3/4, -y+5/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+5/4, -y+3/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+5/4, -y+5/4, z+1/4'

_cell_length_a                   41.659(5)
_cell_length_b                   24.658(3)
_cell_length_c                   4.8420(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4973.8(10)
_cell_formula_units_Z            16
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    12219
_cell_measurement_theta_min      3.305
_cell_measurement_theta_max      27.476

_exptl_crystal_description       prizm
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_F_000             2048
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.411
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   abscore,T.Higashi,RIGAKU
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode x-ray'
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            12219
_diffrn_reflns_av_unetI/netI     0.0643
_diffrn_reflns_av_R_equivalents  0.0680
_diffrn_reflns_limit_h_min       -53
_diffrn_reflns_limit_h_max       54
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.305
_diffrn_reflns_theta_max         27.476
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             2798
_reflns_number_gt                1842
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.751
_reflns_Friedel_fraction_max     0.950
_reflns_Friedel_fraction_full    0.972

_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       RAPID-AUTO
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        RAPID-AUTO
_computing_structure_solution    'SHELXS-97(Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
; 
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. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0567P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 614 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -1.6(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2798
_refine_ls_number_parameters     166
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1202
_refine_ls_wR_factor_gt          0.1018
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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
O1 O 0.08376(6) 0.32455(8) 0.7405(5) 0.0614(6) Uani 1 1 d . . . . .
H1 H 0.0978 0.3163 0.8519 0.092 Uiso 1 1 calc R U . . .
O2 O 0.03651(5) 0.33656(8) 0.3904(5) 0.0607(6) Uani 1 1 d . . . . .
N1 N 0.12525(6) 0.26166(9) 0.9832(5) 0.0474(6) Uani 1 1 d . . . . .
N2 N 0.18477(8) 0.30085(11) 1.4955(7) 0.0708(9) Uani 1 1 d . . . . .
C1 C 0.07469(7) 0.28021(11) 0.5988(6) 0.0453(7) Uani 1 1 d . . . . .
C2 C 0.04951(7) 0.28591(12) 0.4059(6) 0.0473(7) Uani 1 1 d . . . . .
C3 C 0.04012(7) 0.24150(12) 0.2516(6) 0.0516(8) Uani 1 1 d . . . . .
H3 H 0.0240 0.2453 0.1205 0.062 Uiso 1 1 calc R U . . .
C4 C 0.05446(7) 0.19126(12) 0.2894(7) 0.0532(8) Uani 1 1 d . . . . .
H4 H 0.0477 0.1617 0.1851 0.064 Uiso 1 1 calc R U . . .
C5 C 0.07854(7) 0.18511(11) 0.4805(7) 0.0490(7) Uani 1 1 d . . . . .
H5 H 0.0879 0.1513 0.5066 0.059 Uiso 1 1 calc R U . . .
C6 C 0.08897(7) 0.22956(11) 0.6362(6) 0.0427(6) Uani 1 1 d . . . . .
C7 C 0.11465(7) 0.22259(11) 0.8369(6) 0.0458(7) Uani 1 1 d . . . . .
H7 H 0.1231 0.1865 0.8515 0.039(7) Uiso 1 1 d R . . . .
C8 C 0.01067(8) 0.34440(13) 0.1986(8) 0.0586(8) Uani 1 1 d . . . . .
H8A H -0.0063 0.3184 0.2337 0.070 Uiso 1 1 calc R U . . .
H8B H 0.0182 0.3394 0.0108 0.070 Uiso 1 1 calc R U . . .
C9 C -0.00152(8) 0.40102(14) 0.2372(9) 0.0706(10) Uani 1 1 d . . . . .
H9A H -0.0095 0.4052 0.4220 0.106 Uiso 1 1 calc R U . . .
H9B H -0.0185 0.4079 0.1081 0.106 Uiso 1 1 calc R U . . .
H9C H 0.0156 0.4263 0.2062 0.106 Uiso 1 1 calc R U . . .
C10 C 0.15025(7) 0.25413(10) 1.1781(6) 0.0444(7) Uani 1 1 d . . . . .
C11 C 0.16351(7) 0.20509(12) 1.2558(7) 0.0548(8) Uani 1 1 d . . . . .
H11 H 0.1564 0.1729 1.1771 0.066 Uiso 1 1 calc R U . . .
C12 C 0.18754(8) 0.20481(12) 1.4526(7) 0.0586(8) Uani 1 1 d . . . . .
H12 H 0.1969 0.1724 1.5089 0.070 Uiso 1 1 calc R U . . .
C13 C 0.19726(8) 0.25300(13) 1.5625(8) 0.0610(9) Uani 1 1 d . . . . .
H13 H 0.2137 0.2524 1.6926 0.073 Uiso 1 1 calc R U . . .
C14 C 0.16172(8) 0.30021(13) 1.3057(7) 0.0595(9) Uani 1 1 d . . . . .
H14 H 0.1527 0.3332 1.2554 0.071 Uiso 1 1 calc 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
O1 C1 1.345(3) . ?
O1 H1 0.8200 . ?
O2 C2 1.363(3) . ?
O2 C8 1.435(4) . ?
N1 C7 1.275(3) . ?
N1 C10 1.417(4) . ?
N2 C14 1.329(4) . ?
N2 C13 1.330(4) . ?
C1 C6 1.395(4) . ?
C1 C2 1.411(4) . ?
C2 C3 1.382(4) . ?
C3 C4 1.387(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.399(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.455(4) . ?
C7 H7 0.9580 . ?
C8 C9 1.497(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C14 1.379(4) . ?
C10 C11 1.382(4) . ?
C11 C12 1.382(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.363(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C2 O2 C8 117.2(2) . . ?
C7 N1 C10 121.7(2) . . ?
C14 N2 C13 116.2(3) . . ?
O1 C1 C6 122.8(3) . . ?
O1 C1 C2 117.7(2) . . ?
C6 C1 C2 119.5(2) . . ?
O2 C2 C3 125.7(3) . . ?
O2 C2 C1 115.0(2) . . ?
C3 C2 C1 119.3(3) . . ?
C2 C3 C4 120.9(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.2(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 119.9(3) . . ?
C1 C6 C7 120.4(2) . . ?
C5 C6 C7 119.7(3) . . ?
N1 C7 C6 122.4(3) . . ?
N1 C7 H7 122.2 . . ?
C6 C7 H7 115.3 . . ?
O2 C8 C9 107.4(3) . . ?
O2 C8 H8A 110.2 . . ?
C9 C8 H8A 110.2 . . ?
O2 C8 H8B 110.2 . . ?
C9 C8 H8B 110.2 . . ?
H8A C8 H8B 108.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C14 C10 C11 117.4(3) . . ?
C14 C10 N1 116.4(2) . . ?
C11 C10 N1 126.1(3) . . ?
C10 C11 C12 118.8(3) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
C13 C12 C11 118.7(3) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
N2 C13 C12 124.2(3) . . ?
N2 C13 H13 117.9 . . ?
C12 C13 H13 117.9 . . ?
N2 C14 C10 124.8(3) . . ?
N2 C14 H14 117.6 . . ?
C10 C14 H14 117.6 . . ?

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
C8 O2 C2 C3 0.5(4) . . . . ?
C8 O2 C2 C1 -179.6(3) . . . . ?
O1 C1 C2 O2 -1.5(4) . . . . ?
C6 C1 C2 O2 178.1(3) . . . . ?
O1 C1 C2 C3 178.4(3) . . . . ?
C6 C1 C2 C3 -2.0(4) . . . . ?
O2 C2 C3 C4 -178.2(3) . . . . ?
C1 C2 C3 C4 1.9(4) . . . . ?
C2 C3 C4 C5 -0.6(5) . . . . ?
C3 C4 C5 C6 -0.6(5) . . . . ?
O1 C1 C6 C5 -179.6(3) . . . . ?
C2 C1 C6 C5 0.8(4) . . . . ?
O1 C1 C6 C7 0.5(4) . . . . ?
C2 C1 C6 C7 -179.1(2) . . . . ?
C4 C5 C6 C1 0.5(4) . . . . ?
C4 C5 C6 C7 -179.6(3) . . . . ?
C10 N1 C7 C6 179.9(3) . . . . ?
C1 C6 C7 N1 -0.5(4) . . . . ?
C5 C6 C7 N1 179.6(3) . . . . ?
C2 O2 C8 C9 174.8(3) . . . . ?
C7 N1 C10 C14 174.2(3) . . . . ?
C7 N1 C10 C11 -7.4(4) . . . . ?
C14 C10 C11 C12 -0.7(5) . . . . ?
N1 C10 C11 C12 -179.1(3) . . . . ?
C10 C11 C12 C13 0.0(5) . . . . ?
C14 N2 C13 C12 -1.0(6) . . . . ?
C11 C12 C13 N2 1.0(6) . . . . ?
C13 N2 C14 C10 0.1(6) . . . . ?
C11 C10 C14 N2 0.7(5) . . . . ?
N1 C10 C14 N2 179.2(3) . . . . ?

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
O1 H1 N1 0.82 1.88 2.602(3) 146.5 .

_refine_diff_density_max         0.260
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.061


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
_chemical_compound_source        non-photochromic
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC19
_database_code_depnum_ccdc_archive 'CCDC 1814049'
_audit_update_record             
;
2017-12-30 deposited with the CCDC.
2018-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        3hydroxy-6-[(E)-3-pyridyliminomethyl]phenol
_chemical_name_common            4OH-3SAP
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 N2 O2'
_chemical_formula_sum            'C12 H10 N2 O2'
_chemical_formula_weight         214.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   13.1386(3)
_cell_length_b                   7.1572(2)
_cell_length_c                   11.8627(2)
_cell_angle_alpha                90
_cell_angle_beta                 116.8000(10)
_cell_angle_gamma                90
_cell_volume                     995.69(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6505
_cell_measurement_theta_min      3.769
_cell_measurement_theta_max      68.198

_exptl_crystal_description       prizm
_exptl_crystal_colour            'yellow orange'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.819
_shelx_estimated_absorpt_T_min   0.901
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.774
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_process_details   abscore,T.Higashi,RIGAKU
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating anode x-ray'
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID2'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            6505
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.769
_diffrn_reflns_theta_max         68.198
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             1762
_reflns_number_gt                1540
_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       RAPID-AUTO
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        RAPID-AUTO
_computing_structure_solution    'SHELXS-97(Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
; 
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. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0728P)²+0.1423P] 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_number_reflns         1762
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1201
_refine_ls_wR_factor_gt          0.1153
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_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
O1 O 0.41027(8) 0.19366(16) 0.51983(9) 0.0526(3) Uani 1 1 d . . . . .
H1A H 0.469304 0.207892 0.513279 0.079 Uiso 1 1 calc R U . . .
O2 O 0.01571(8) 0.29710(16) 0.29700(8) 0.0477(3) Uani 1 1 d . . . . .
H2A H -0.033330 0.300479 0.223284 0.072 Uiso 1 1 calc R U . . .
N1 N 0.54008(9) 0.30953(15) 0.41988(10) 0.0357(3) Uani 1 1 d . . . . .
N2 N 0.84758(9) 0.25110(16) 0.55557(10) 0.0400(3) Uani 1 1 d . . . . .
C1 C 0.32159(11) 0.26651(18) 0.41704(11) 0.0346(3) Uani 1 1 d . . . . .
C2 C 0.21270(11) 0.24821(18) 0.40582(11) 0.0370(3) Uani 1 1 d . . . . .
H2 H 0.201823 0.187499 0.468860 0.044 Uiso 1 1 calc R U . . .
C3 C 0.11950(10) 0.31939(18) 0.30158(11) 0.0341(3) Uani 1 1 d . . . . .
C4 C 0.13487(10) 0.41289(18) 0.20666(11) 0.0362(3) Uani 1 1 d . . . . .
H4 H 0.072704 0.461474 0.136752 0.043 Uiso 1 1 calc R U . . .
C5 C 0.24331(10) 0.43159(18) 0.21857(11) 0.0336(3) Uani 1 1 d . . . . .
H5 H 0.253450 0.494374 0.155732 0.040 Uiso 1 1 calc R U . . .
C6 C 0.33925(10) 0.35956(16) 0.32192(10) 0.0306(3) Uani 1 1 d . . . . .
C7 C 0.45089(10) 0.37978(17) 0.32872(11) 0.0330(3) Uani 1 1 d . . . . .
H7 H 0.458706 0.445460 0.265421 0.040 Uiso 1 1 calc R U . . .
C8 C 0.64975(10) 0.32775(17) 0.42716(11) 0.0326(3) Uani 1 1 d . . . . .
C9 C 0.67799(11) 0.41708(19) 0.34066(12) 0.0398(3) Uani 1 1 d . . . . .
H9 H 0.621750 0.472327 0.268487 0.048 Uiso 1 1 calc R U . . .
C10 C 0.79076(11) 0.4222(2) 0.36384(12) 0.0412(3) Uani 1 1 d . . . . .
H10 H 0.811473 0.481850 0.307595 0.049 Uiso 1 1 calc R U . . .
C11 C 0.87253(11) 0.33817(19) 0.47122(12) 0.0400(3) Uani 1 1 d . . . . .
H11 H 0.948184 0.342161 0.485608 0.048 Uiso 1 1 calc R U . . .
C12 C 0.73847(10) 0.24818(19) 0.53287(12) 0.0362(3) Uani 1 1 d . . . . .
H12 H 0.720530 0.189169 0.591470 0.043 Uiso 1 1 calc 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
O1 C1 1.3546(15) . ?
O1 H1A 0.8200 . ?
O2 C3 1.3494(14) . ?
O2 H2A 0.8200 . ?
N1 C7 1.2856(16) . ?
N1 C8 1.4102(16) . ?
N2 C12 1.3342(15) . ?
N2 C11 1.3389(17) . ?
C1 C2 1.3820(17) . ?
C1 C6 1.4166(17) . ?
C2 C3 1.3866(17) . ?
C2 H2 0.9300 . ?
C3 C4 1.4006(17) . ?
C4 C5 1.3734(16) . ?
C4 H4 0.9300 . ?
C5 C6 1.4016(16) . ?
C5 H5 0.9300 . ?
C6 C7 1.4395(16) . ?
C7 H7 0.9300 . ?
C8 C12 1.3920(17) . ?
C8 C9 1.3938(17) . ?
C9 C10 1.3802(17) . ?
C9 H9 0.9300 . ?
C10 C11 1.3802(19) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1A 109.5 . . ?
C3 O2 H2A 109.5 . . ?
C7 N1 C8 122.28(11) . . ?
C12 N2 C11 117.34(11) . . ?
O1 C1 C2 118.89(11) . . ?
O1 C1 C6 120.97(11) . . ?
C2 C1 C6 120.14(11) . . ?
C1 C2 C3 120.71(11) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
O2 C3 C2 117.55(11) . . ?
O2 C3 C4 122.24(11) . . ?
C2 C3 C4 120.20(11) . . ?
C5 C4 C3 118.87(11) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 122.43(11) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
C5 C6 C1 117.65(11) . . ?
C5 C6 C7 120.25(11) . . ?
C1 C6 C7 122.10(11) . . ?
N1 C7 C6 121.81(11) . . ?
N1 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C12 C8 C9 117.27(11) . . ?
C12 C8 N1 115.77(10) . . ?
C9 C8 N1 126.96(11) . . ?
C10 C9 C8 118.94(12) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C11 C10 C9 119.42(12) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
N2 C11 C10 122.80(12) . . ?
N2 C11 H11 118.6 . . ?
C10 C11 H11 118.6 . . ?
N2 C12 C8 124.23(11) . . ?
N2 C12 H12 117.9 . . ?
C8 C12 H12 117.9 . . ?

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
O1 C1 C2 C3 -179.45(12) . . . . ?
C6 C1 C2 C3 0.3(2) . . . . ?
C1 C2 C3 O2 -179.77(11) . . . . ?
C1 C2 C3 C4 -0.69(19) . . . . ?
O2 C3 C4 C5 179.37(11) . . . . ?
C2 C3 C4 C5 0.33(19) . . . . ?
C3 C4 C5 C6 0.39(19) . . . . ?
C4 C5 C6 C1 -0.74(19) . . . . ?
C4 C5 C6 C7 178.79(11) . . . . ?
O1 C1 C6 C5 -179.85(11) . . . . ?
C2 C1 C6 C5 0.38(18) . . . . ?
O1 C1 C6 C7 0.6(2) . . . . ?
C2 C1 C6 C7 -179.15(11) . . . . ?
C8 N1 C7 C6 179.70(10) . . . . ?
C5 C6 C7 N1 -177.46(12) . . . . ?
C1 C6 C7 N1 2.1(2) . . . . ?
C7 N1 C8 C12 178.53(11) . . . . ?
C7 N1 C8 C9 -1.1(2) . . . . ?
C12 C8 C9 C10 -0.06(18) . . . . ?
N1 C8 C9 C10 179.58(12) . . . . ?
C8 C9 C10 C11 0.4(2) . . . . ?
C12 N2 C11 C10 -0.29(19) . . . . ?
C9 C10 C11 N2 -0.3(2) . . . . ?
C11 N2 C12 C8 0.69(19) . . . . ?
C9 C8 C12 N2 -0.52(19) . . . . ?
N1 C8 C12 N2 179.80(11) . . . . ?

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
O2 H2A N2 0.82 1.93 2.7380(14) 167.0 4_465
O1 H1A N1 0.82 1.88 2.6126(14) 147.4 .

_refine_diff_density_max         0.189
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.050


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: THF'
_chemical_compound_source        non-photochromic
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC20
_database_code_depnum_ccdc_archive 'CCDC 1814066'
_audit_update_record             
;
2017-12-30 deposited with the CCDC.
2018-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
'4-bromo-2-[(E)-3-pyridyliminomethyl]phenol, 1,4-diiodobiphenyl'
_chemical_name_common            5Br3SAP-14IbiPh
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 Br N2 O, 0.5(I2 C12 H8)'
_chemical_formula_sum            'C18 H13 Br I N2 O'
_chemical_formula_weight         480.11

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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                   37.851(2)
_cell_length_b                   6.9901(4)
_cell_length_c                   6.168(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.041(2)
_cell_angle_gamma                90
_cell_volume                     1631.9(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    8123
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      27.47

_exptl_crystal_description       palte
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.954
_exptl_crystal_F_000             924
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.040
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    4.416
_shelx_estimated_absorpt_T_min   0.843
_shelx_estimated_absorpt_T_max   0.917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.433
_exptl_absorpt_correction_T_max  0.917
_exptl_absorpt_process_details   'Absorption was corrected by ABSCOR'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode X-ray tube'
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID IP Area Detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12155
_diffrn_reflns_av_unetI/netI     0.0736
_diffrn_reflns_av_R_equivalents  0.0837
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.107
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2976
_reflns_number_gt                2637
_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       'PROCESS-AUTO (Rigaku, 1998)'
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'PROCESS-AUTO (Rigaku, 1998)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2008)'
_computing_publication_material  'SHELXL-2014/07 (Sheldrick, 2014)'
_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)+(0.0334P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2976
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.0838
_refine_ls_wR_factor_gt          0.0813
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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
Br1 Br 0.46794(2) -0.06977(6) 0.80932(6) 0.03436(14) Uani 1 1 d . . . . .
O1 O 0.33921(7) 0.0710(4) 0.2554(4) 0.0328(6) Uani 1 1 d . . . . .
H1A H 0.320584 0.057680 0.327755 0.049 Uiso 1 1 d R U . . .
N1 N 0.30088(8) -0.0175(4) 0.5897(5) 0.0254(7) Uani 1 1 d . . . . .
N2 N 0.20503(9) -0.0647(4) 0.6470(5) 0.0317(7) Uani 1 1 d . . . . .
C1 C 0.36761(10) 0.0376(5) 0.3846(6) 0.0249(8) Uani 1 1 d . . . . .
C2 C 0.40132(10) 0.0721(5) 0.2989(6) 0.0276(8) Uani 1 1 d . . . . .
H2 H 0.403825 0.119095 0.155221 0.033 Uiso 1 1 calc R U . . .
C3 C 0.43081(11) 0.0376(5) 0.4243(6) 0.0276(9) Uani 1 1 d . . . . .
H3 H 0.453685 0.059934 0.366326 0.033 Uiso 1 1 calc R U . . .
C4 C 0.42717(11) -0.0304(5) 0.6367(6) 0.0244(8) Uani 1 1 d . . . . .
C5 C 0.39410(10) -0.0649(5) 0.7231(6) 0.0235(8) Uani 1 1 d . . . . .
H5 H 0.391890 -0.113443 0.866290 0.028 Uiso 1 1 calc R U . . .
C6 C 0.36397(10) -0.0283(5) 0.5996(5) 0.0228(8) Uani 1 1 d . . . . .
C7 C 0.32911(10) -0.0476(4) 0.7007(6) 0.0244(8) Uani 1 1 d . . . . .
H1 H 0.327364 -0.082661 0.849094 0.029 Uiso 1 1 calc R U . . .
C8 C 0.26731(10) -0.0123(5) 0.6940(6) 0.0243(8) Uani 1 1 d . . . . .
C9 C 0.23825(10) -0.0705(5) 0.5719(6) 0.0264(8) Uani 1 1 d . . . . .
H9 H 0.242152 -0.116372 0.428918 0.032 Uiso 1 1 calc R U . . .
C10 C 0.20013(11) 0.0025(6) 0.8483(7) 0.0326(9) Uani 1 1 d . . . . .
H10 H 0.176795 0.005700 0.904698 0.039 Uiso 1 1 calc R U . . .
C11 C 0.22745(11) 0.0673(5) 0.9774(6) 0.0304(9) Uani 1 1 d . . . . .
H11 H 0.222690 0.116355 1.118071 0.037 Uiso 1 1 calc R U . . .
C12 C 0.26167(11) 0.0605(5) 0.9012(6) 0.0269(8) Uani 1 1 d . . . . .
H12 H 0.280839 0.104148 0.987560 0.032 Uiso 1 1 calc R U . . .
I1 I 0.13572(2) -0.03431(3) 0.38665(4) 0.02722(12) Uani 1 1 d . . . . .
C13 C 0.08571(10) -0.0166(5) 0.2408(6) 0.0225(8) Uani 1 1 d . . . . .
C14 C 0.08107(10) 0.0595(5) 0.0339(6) 0.0246(8) Uani 1 1 d . . . . .
H14 H 0.100935 0.105149 -0.044647 0.029 Uiso 1 1 calc R U . . .
C15 C 0.04800(10) 0.0689(5) -0.0576(6) 0.0236(8) Uani 1 1 d . . . . .
H15 H 0.045383 0.124166 -0.197403 0.028 Uiso 1 1 calc R U . . .
C16 C 0.01784(10) -0.0013(5) 0.0506(6) 0.0201(7) Uani 1 1 d . . . . .
C17 C 0.02330(10) -0.0754(5) 0.2607(6) 0.0235(8) Uani 1 1 d . . . . .
H17 H 0.003557 -0.120799 0.340566 0.028 Uiso 1 1 calc R U . . .
C18 C 0.05637(10) -0.0839(5) 0.3537(5) 0.0231(7) Uani 1 1 d . . . . .
H18 H 0.059168 -0.135688 0.495052 0.028 Uiso 1 1 calc 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
Br1 C4 1.894(4) . ?
O1 C1 1.358(5) . ?
O1 H1A 0.8401 . ?
N1 C7 1.286(5) . ?
N1 C8 1.425(5) . ?
N2 C10 1.341(5) . ?
N2 C9 1.341(5) . ?
C1 C2 1.402(5) . ?
C1 C6 1.410(5) . ?
C2 C3 1.379(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.400(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(5) . ?
C5 C6 1.395(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.466(5) . ?
C7 H1 0.9500 . ?
C8 C12 1.392(5) . ?
C8 C9 1.393(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.381(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.379(5) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
I1 C13 2.099(4) . ?
C13 C18 1.393(5) . ?
C13 C14 1.394(5) . ?
C14 C15 1.374(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.411(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.411(5) . ?
C16 C16 1.487(8) 3 ?
C17 C18 1.378(5) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1A 109.5 . . ?
C7 N1 C8 120.3(3) . . ?
C10 N2 C9 117.4(4) . . ?
O1 C1 C2 118.0(3) . . ?
O1 C1 C6 122.0(3) . . ?
C2 C1 C6 120.0(4) . . ?
C3 C2 C1 119.7(4) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 120.3(4) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 120.6(4) . . ?
C5 C4 Br1 119.7(3) . . ?
C3 C4 Br1 119.6(3) . . ?
C4 C5 C6 119.9(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C1 119.5(3) . . ?
C5 C6 C7 119.1(3) . . ?
C1 C6 C7 121.2(3) . . ?
N1 C7 C6 120.4(3) . . ?
N1 C7 H1 119.8 . . ?
C6 C7 H1 119.8 . . ?
C12 C8 C9 118.8(4) . . ?
C12 C8 N1 124.1(3) . . ?
C9 C8 N1 116.9(3) . . ?
N2 C9 C8 123.0(4) . . ?
N2 C9 H9 118.5 . . ?
C8 C9 H9 118.5 . . ?
N2 C10 C11 123.0(4) . . ?
N2 C10 H10 118.5 . . ?
C11 C10 H10 118.5 . . ?
C12 C11 C10 119.7(4) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C8 118.1(4) . . ?
C11 C12 H12 121.0 . . ?
C8 C12 H12 121.0 . . ?
C18 C13 C14 119.1(3) . . ?
C18 C13 I1 119.0(3) . . ?
C14 C13 I1 121.9(3) . . ?
C15 C14 C13 120.6(3) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 121.8(3) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 H15 119.1 . . ?
C17 C16 C15 116.4(3) . . ?
C17 C16 C16 121.5(4) . 3 ?
C15 C16 C16 122.1(4) . 3 ?
C18 C17 C16 122.1(3) . . ?
C18 C17 H17 119.0 . . ?
C16 C17 H17 119.0 . . ?
C17 C18 C13 120.1(3) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?

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
O1 C1 C2 C3 -179.2(3) . . . . ?
C6 C1 C2 C3 1.3(5) . . . . ?
C1 C2 C3 C4 -0.4(5) . . . . ?
C2 C3 C4 C5 0.4(5) . . . . ?
C2 C3 C4 Br1 -178.1(3) . . . . ?
C3 C4 C5 C6 -1.3(5) . . . . ?
Br1 C4 C5 C6 177.3(2) . . . . ?
C4 C5 C6 C1 2.1(5) . . . . ?
C4 C5 C6 C7 -174.0(3) . . . . ?
O1 C1 C6 C5 178.4(3) . . . . ?
C2 C1 C6 C5 -2.2(5) . . . . ?
O1 C1 C6 C7 -5.6(5) . . . . ?
C2 C1 C6 C7 173.9(3) . . . . ?
C8 N1 C7 C6 -172.0(3) . . . . ?
C5 C6 C7 N1 -179.0(3) . . . . ?
C1 C6 C7 N1 4.9(5) . . . . ?
C7 N1 C8 C12 35.2(5) . . . . ?
C7 N1 C8 C9 -150.0(3) . . . . ?
C10 N2 C9 C8 0.7(5) . . . . ?
C12 C8 C9 N2 -1.9(5) . . . . ?
N1 C8 C9 N2 -177.0(3) . . . . ?
C9 N2 C10 C11 1.0(6) . . . . ?
N2 C10 C11 C12 -1.4(6) . . . . ?
C10 C11 C12 C8 0.1(5) . . . . ?
C9 C8 C12 C11 1.4(5) . . . . ?
N1 C8 C12 C11 176.1(3) . . . . ?
C18 C13 C14 C15 0.3(5) . . . . ?
I1 C13 C14 C15 179.9(3) . . . . ?
C13 C14 C15 C16 -1.5(5) . . . . ?
C14 C15 C16 C17 2.2(5) . . . . ?
C14 C15 C16 C16 -177.5(4) . . . 3 ?
C15 C16 C17 C18 -1.7(5) . . . . ?
C16 C16 C17 C18 178.0(4) 3 . . . ?
C16 C17 C18 C13 0.6(5) . . . . ?
C14 C13 C18 C17 0.2(5) . . . . ?
I1 C13 C18 C17 -179.4(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
O1 H1A N1 0.84 1.86 2.597(4) 146.3 .
C14 H14 I1 0.95 3.30 4.016(3) 133.3 4_565

_refine_diff_density_max         1.491
_refine_diff_density_min         -0.784
_refine_diff_density_rms         0.215


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
_chemical_compound_source        non-photochromic
