# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_34LGF1
_database_code_depnum_ccdc_archive 'CCDC 1991574'
loop_
_audit_author_name
_audit_author_address
'Iwona Bryndal'
;Department of Drugs Technology, Faculty of Pharmacy, Wroclaw Medical University
Poland
;

_audit_update_record             
;
2020-03-19 deposited with the CCDC.	2020-06-04 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        2,5-Dinitrophenol
_chemical_name_common            2,5-Dinitrophenol
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H4 N2 O5'
_chemical_formula_sum            'C6 H4 N2 O5'
_chemical_formula_weight         184.11

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'
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                   5.4780(15)
_cell_length_b                   5.2268(15)
_cell_length_c                   12.296(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.28(5)
_cell_angle_gamma                90
_cell_volume                     347.46(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    630
_cell_measurement_theta_min      3.351
_cell_measurement_theta_max      28.751

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.760
_exptl_crystal_F_000             188
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.157
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.3359
_diffrn_reflns_number            1693
_diffrn_reflns_av_unetI/netI     0.0856
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.358
_diffrn_reflns_theta_max         28.815
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.899
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.899
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.592
_diffrn_reflns_point_group_measured_fraction_full 0.652
_reflns_number_total             1072
_reflns_number_gt                797
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.191
_reflns_Friedel_fraction_max     0.213
_reflns_Friedel_fraction_full    0.242

_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       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2015)'
_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)+(0.0955P)²] 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 81 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -9.6(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1072
_refine_ls_number_parameters     119
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1033
_refine_ls_R_factor_gt           0.0771
_refine_ls_wR_factor_ref         0.2074
_refine_ls_wR_factor_gt          0.1764
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_restrained_S_all      1.108
_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 0.1638(10) 0.6864(12) 0.3334(5) 0.0253(14) Uani 1 1 d . . . . .
C2 C 0.3667(10) 0.8277(12) 0.3091(5) 0.0209(12) Uani 1 1 d . . . . .
C3 C 0.4806(10) 0.7710(13) 0.2178(4) 0.0265(14) Uani 1 1 d . . . . .
H3 H 0.619458 0.867452 0.204108 0.032 Uiso 1 1 calc R U . . .
C4 C 0.3904(10) 0.5748(12) 0.1480(5) 0.0253(13) Uani 1 1 d . . . . .
H4 H 0.463369 0.533436 0.085237 0.030 Uiso 1 1 calc R U . . .
C5 C 0.1900(10) 0.4409(12) 0.1730(5) 0.0251(13) Uani 1 1 d . . . . .
C6 C 0.0736(10) 0.4910(11) 0.2617(4) 0.0234(12) Uani 1 1 d . . . . .
H6 H -0.066031 0.393572 0.273681 0.028 Uiso 1 1 calc R U . . .
O1 O 0.0454(7) 0.7263(9) 0.4195(3) 0.0324(11) Uani 1 1 d . . . . .
H1 H 0.129850 0.824658 0.464761 0.049 Uiso 1 1 calc R U . . .
N1 N 0.4642(8) 1.0416(11) 0.3798(4) 0.0246(11) Uani 1 1 d . . . . .
O2 O 0.3599(7) 1.0995(8) 0.4582(3) 0.0304(11) Uani 1 1 d . . . . .
O3 O 0.6448(7) 1.1584(10) 0.3568(3) 0.0343(11) Uani 1 1 d . . . . .
N2 N 0.0891(9) 0.2290(11) 0.0983(4) 0.0279(12) Uani 1 1 d . . . . .
O4 O 0.2083(7) 0.1590(9) 0.0291(3) 0.0330(11) Uani 1 1 d . . . . .
O5 O -0.1096(8) 0.1351(10) 0.1115(3) 0.0363(12) 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 1.344(7) . ?
C1 C6 1.387(8) . ?
C1 C2 1.406(8) . ?
C2 C3 1.401(7) . ?
C2 N1 1.463(8) . ?
C3 C4 1.377(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.377(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.375(7) . ?
C5 N2 1.487(8) . ?
C6 H6 0.9500 . ?
O1 H1 0.8400 . ?
N1 O3 1.234(6) . ?
N1 O2 1.234(5) . ?
N2 O4 1.210(6) . ?
N2 O5 1.228(6) . ?

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 116.6(5) . . ?
O1 C1 C2 125.7(6) . . ?
C6 C1 C2 117.7(5) . . ?
C3 C2 C1 121.9(5) . . ?
C3 C2 N1 118.1(5) . . ?
C1 C2 N1 120.0(5) . . ?
C4 C3 C2 119.7(5) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 117.3(5) . . ?
C3 C4 H4 121.3 . . ?
C5 C4 H4 121.3 . . ?
C6 C5 C4 124.6(6) . . ?
C6 C5 N2 117.2(5) . . ?
C4 C5 N2 118.1(5) . . ?
C5 C6 C1 118.8(5) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
C1 O1 H1 109.5 . . ?
O3 N1 O2 123.1(6) . . ?
O3 N1 C2 118.1(5) . . ?
O2 N1 C2 118.7(5) . . ?
O4 N2 O5 124.2(6) . . ?
O4 N2 C5 118.0(5) . . ?
O5 N2 C5 117.8(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 179.4(6) . . . . ?
C6 C1 C2 C3 -1.8(8) . . . . ?
O1 C1 C2 N1 -0.9(8) . . . . ?
C6 C1 C2 N1 178.0(5) . . . . ?
C1 C2 C3 C4 1.2(8) . . . . ?
N1 C2 C3 C4 -178.5(5) . . . . ?
C2 C3 C4 C5 -0.5(8) . . . . ?
C3 C4 C5 C6 0.6(9) . . . . ?
C3 C4 C5 N2 179.7(5) . . . . ?
C4 C5 C6 C1 -1.2(8) . . . . ?
N2 C5 C6 C1 179.6(5) . . . . ?
O1 C1 C6 C5 -179.3(5) . . . . ?
C2 C1 C6 C5 1.7(8) . . . . ?
C3 C2 N1 O3 -1.3(8) . . . . ?
C1 C2 N1 O3 178.9(5) . . . . ?
C3 C2 N1 O2 177.4(5) . . . . ?
C1 C2 N1 O2 -2.4(7) . . . . ?
C6 C5 N2 O4 -170.0(5) . . . . ?
C4 C5 N2 O4 10.8(8) . . . . ?
C6 C5 N2 O5 9.6(7) . . . . ?
C4 C5 N2 O5 -169.7(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 O2 0.84 1.92 2.595(6) 136.4 . yes
O1 H1 N1 0.84 2.52 2.928(7) 111.1 . yes
O1 H1 O3 0.84 2.49 3.011(6) 120.8 2_646 yes
C3 H3 O5 0.95 2.45 3.364(8) 161.4 1_665 yes
C4 H4 O4 0.95 2.54 3.364(7) 145.0 2_655 yes
C6 H6 O3 0.95 2.36 3.286(7) 163.4 1_445 yes

_refine_diff_density_max         0.383
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.096


# start Validation Reply Form
_vrf_PLAT915_34LGF1              
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         21 %     
RESPONSE: The reliable determination of the  absolute structure of 
a non-centrosymmetric crystal structure could not be determined; 
because there are no heavy atoms in the molecules.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_2ap6f1
_database_code_depnum_ccdc_archive 'CCDC 1991575'
loop_
_audit_author_name
_audit_author_address
'Iwona Bryndal'
;Department of Drugs Technology, Faculty of Pharmacy, Wroclaw Medical University
Poland
;
_audit_update_record             
;
2020-03-19 deposited with the CCDC.	2020-06-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        '2-aminopyridinium 2,5-dinitrophenolate'
_chemical_name_common            '2-aminopyridinium 2,5-dinitrophenolate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H3 N2 O5, C5 H7 N2'
_chemical_formula_sum            'C11 H10 N4 O5'
_chemical_formula_weight         278.23

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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -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, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   30.030(9)
_cell_length_b                   3.7280(9)
_cell_length_c                   21.080(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2359.9(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    494
_cell_measurement_theta_min      2.804
_cell_measurement_theta_max      30.660

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_F_000             1152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.127
_shelx_estimated_absorpt_T_min   0.928
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3456
_diffrn_reflns_number            5448
_diffrn_reflns_av_unetI/netI     0.1366
_diffrn_reflns_av_R_equivalents  0.0790
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.201
_diffrn_reflns_theta_max         30.700
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.816
_diffrn_measured_fraction_theta_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.816
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.519
_diffrn_reflns_point_group_measured_fraction_full 0.639
_reflns_number_total             3817
_reflns_number_gt                2041
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.242
_reflns_Friedel_fraction_max     0.208
_reflns_Friedel_fraction_full    0.297

_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2015)'
_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)+(0.0212P)²] 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 297 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.7(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3817
_refine_ls_number_parameters     355
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1611
_refine_ls_R_factor_gt           0.0811
_refine_ls_wR_factor_ref         0.1283
_refine_ls_wR_factor_gt          0.1027
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.018
_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
N1A N 0.5805(2) -0.401(2) 0.4111(3) 0.0148(15) Uani 1 1 d . . . . .
H1A H 0.567905 -0.334656 0.446904 0.018 Uiso 1 1 calc R U . . .
C2A C 0.6242(2) -0.327(2) 0.4019(4) 0.0137(17) Uani 1 1 d . . . . .
C3A C 0.6444(2) -0.441(2) 0.3441(4) 0.0145(19) Uani 1 1 d . . . . .
H3A H 0.675130 -0.399478 0.336416 0.017 Uiso 1 1 calc R U . . .
C4A C 0.6184(3) -0.611(2) 0.2999(4) 0.018(2) Uani 1 1 d . . . . .
H4A H 0.631420 -0.684032 0.260968 0.022 Uiso 1 1 calc R U . . .
C5A C 0.5733(3) -0.679(2) 0.3104(4) 0.017(2) Uani 1 1 d . . . . .
H5A H 0.555682 -0.795433 0.279150 0.020 Uiso 1 1 calc R U . . .
C6A C 0.5554(3) -0.574(3) 0.3669(4) 0.0177(19) Uani 1 1 d . . . . .
H6A H 0.524895 -0.621492 0.375552 0.021 Uiso 1 1 calc R U . . .
N2A N 0.64545(19) -0.150(2) 0.4474(3) 0.0161(17) Uani 1 1 d . . . . .
H21A H 0.631157 -0.084113 0.481922 0.019 Uiso 1 1 calc R U . . .
H22A H 0.673857 -0.097280 0.442903 0.019 Uiso 1 1 calc R U . . .
N1B N 0.7880(2) 0.8920(19) 0.5897(3) 0.0138(12) Uani 1 1 d . . . . .
H1B H 0.801120 0.831516 0.553961 0.017 Uiso 1 1 calc R U . . .
C2B C 0.7443(2) 0.805(2) 0.5980(4) 0.0138(12) Uani 1 1 d . . . . .
C3B C 0.7237(3) 0.906(2) 0.6555(4) 0.017(2) Uani 1 1 d . . . . .
H3B H 0.693298 0.850503 0.662776 0.020 Uiso 1 1 calc R U . . .
C4B C 0.7478(3) 1.085(2) 0.7007(4) 0.0154(19) Uani 1 1 d . . . . .
H4B H 0.734014 1.153165 0.739402 0.018 Uiso 1 1 calc R U . . .
C5B C 0.7932(3) 1.169(2) 0.6901(4) 0.015(2) Uani 1 1 d . . . . .
H5B H 0.810038 1.292400 0.721318 0.018 Uiso 1 1 calc R U . . .
C6B C 0.8120(3) 1.068(2) 0.6343(4) 0.0161(19) Uani 1 1 d . . . . .
H6B H 0.842401 1.122131 0.626452 0.019 Uiso 1 1 calc R U . . .
N2B N 0.7233(2) 0.630(2) 0.5517(3) 0.0175(17) Uani 1 1 d . . . . .
H21B H 0.737578 0.573213 0.516714 0.021 Uiso 1 1 calc R U . . .
H22B H 0.695062 0.571295 0.556206 0.021 Uiso 1 1 calc R U . . .
O1C O 0.5665(2) -0.0218(18) 0.5124(3) 0.0243(15) Uani 1 1 d . . . . .
C1C C 0.5450(2) 0.056(2) 0.5638(3) 0.0140(18) Uani 1 1 d . . . . .
C2C C 0.5637(2) 0.228(2) 0.6187(4) 0.0143(18) Uani 1 1 d . . . . .
C3C C 0.5392(3) 0.303(3) 0.6728(4) 0.017(2) Uani 1 1 d . . . . .
H3C H 0.553487 0.411391 0.708185 0.021 Uiso 1 1 calc R U . . .
C4C C 0.4942(2) 0.222(2) 0.6760(4) 0.018(2) Uani 1 1 d . . . . .
H4C H 0.476981 0.274377 0.712644 0.022 Uiso 1 1 calc R U . . .
C5C C 0.4755(2) 0.059(2) 0.6227(3) 0.0131(17) Uani 1 1 d . . . . .
C6C C 0.4979(3) -0.019(2) 0.5685(4) 0.0162(18) Uani 1 1 d . . . . .
H6C H 0.482579 -0.123874 0.533664 0.019 Uiso 1 1 calc R U . . .
N1C N 0.6101(2) 0.336(2) 0.6200(3) 0.0188(17) Uani 1 1 d . . . . .
O2C O 0.63507(16) 0.2577(19) 0.5749(2) 0.0242(15) Uani 1 1 d . . . . .
O3C O 0.62391(18) 0.4977(18) 0.6668(3) 0.0287(16) Uani 1 1 d . . . . .
N2C N 0.4272(2) -0.039(2) 0.6262(3) 0.0174(16) Uani 1 1 d . . . . .
O4C O 0.40541(17) 0.0648(19) 0.6716(3) 0.0236(16) Uani 1 1 d . . . . .
O5C O 0.41120(17) -0.2181(19) 0.5818(3) 0.0288(16) Uani 1 1 d . . . . .
O1D O 0.80456(17) 0.5147(18) 0.4865(2) 0.0213(14) Uani 1 1 d . . . . .
C1D C 0.8246(3) 0.445(3) 0.4348(4) 0.020(2) Uani 1 1 d . . . . .
C2D C 0.8052(2) 0.285(2) 0.3793(4) 0.0137(18) Uani 1 1 d . . . . .
C3D C 0.8292(2) 0.223(2) 0.3233(4) 0.0134(19) Uani 1 1 d . . . . .
H3D H 0.814625 0.115675 0.288073 0.016 Uiso 1 1 calc R U . . .
C4D C 0.8733(2) 0.316(2) 0.3183(4) 0.0116(18) Uani 1 1 d . . . . .
H4D H 0.889733 0.276887 0.280462 0.014 Uiso 1 1 calc R U . . .
C5D C 0.8927(2) 0.472(2) 0.3723(4) 0.0168(19) Uani 1 1 d . . . . .
C6D C 0.8708(2) 0.540(2) 0.4283(4) 0.0181(19) Uani 1 1 d . . . . .
H6D H 0.886102 0.649203 0.462645 0.022 Uiso 1 1 calc R U . . .
N1D N 0.7592(2) 0.171(2) 0.3804(3) 0.0163(16) Uani 1 1 d . . . . .
O2D O 0.73503(16) 0.2387(18) 0.4267(2) 0.0236(15) Uani 1 1 d . . . . .
O3D O 0.74476(18) -0.005(2) 0.3340(3) 0.0269(17) Uani 1 1 d . . . . .
N2D N 0.9409(2) 0.572(2) 0.3688(3) 0.0249(18) Uani 1 1 d . . . . .
O4D O 0.96207(18) 0.474(2) 0.3210(3) 0.0298(16) Uani 1 1 d . . . . .
O5D O 0.95720(17) 0.7423(19) 0.4131(3) 0.0299(17) 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
N1A C2A 1.353(9) . ?
N1A C6A 1.360(10) . ?
N1A H1A 0.8800 . ?
C2A N2A 1.328(9) . ?
C2A C3A 1.426(10) . ?
C3A C4A 1.372(10) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.393(11) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.367(11) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
N2A H21A 0.8800 . ?
N2A H22A 0.8800 . ?
N1B C6B 1.355(10) . ?
N1B C2B 1.362(9) . ?
N1B H1B 0.8800 . ?
C2B N2B 1.332(9) . ?
C2B C3B 1.412(10) . ?
C3B C4B 1.370(11) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.414(11) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.358(11) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
N2B H21B 0.8800 . ?
N2B H22B 0.8800 . ?
O1C C1C 1.296(9) . ?
C1C C2C 1.437(11) . ?
C1C C6C 1.445(11) . ?
C2C C3C 1.385(11) . ?
C2C N1C 1.450(9) . ?
C3C C4C 1.388(11) . ?
C3C H3C 0.9500 . ?
C4C C5C 1.394(10) . ?
C4C H4C 0.9500 . ?
C5C C6C 1.357(10) . ?
C5C N2C 1.498(9) . ?
C6C H6C 0.9500 . ?
N1C O3C 1.228(8) . ?
N1C O2C 1.247(8) . ?
N2C O4C 1.222(8) . ?
N2C O5C 1.248(8) . ?
O1D C1D 1.270(9) . ?
C1D C2D 1.437(11) . ?
C1D C6D 1.438(11) . ?
C2D C3D 1.403(10) . ?
C2D N1D 1.445(9) . ?
C3D C4D 1.372(11) . ?
C3D H3D 0.9500 . ?
C4D C5D 1.405(11) . ?
C4D H4D 0.9500 . ?
C5D C6D 1.376(10) . ?
C5D N2D 1.495(10) . ?
C6D H6D 0.9500 . ?
N1D O2D 1.241(7) . ?
N1D O3D 1.256(8) . ?
N2D O5D 1.229(8) . ?
N2D O4D 1.248(8) . ?

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
C2A N1A C6A 122.4(7) . . ?
C2A N1A H1A 118.8 . . ?
C6A N1A H1A 118.8 . . ?
N2A C2A N1A 117.7(7) . . ?
N2A C2A C3A 124.0(7) . . ?
N1A C2A C3A 118.3(7) . . ?
C4A C3A C2A 118.4(7) . . ?
C4A C3A H3A 120.8 . . ?
C2A C3A H3A 120.8 . . ?
C3A C4A C5A 122.0(8) . . ?
C3A C4A H4A 119.0 . . ?
C5A C4A H4A 119.0 . . ?
C6A C5A C4A 117.9(8) . . ?
C6A C5A H5A 121.0 . . ?
C4A C5A H5A 121.0 . . ?
N1A C6A C5A 120.9(7) . . ?
N1A C6A H6A 119.5 . . ?
C5A C6A H6A 119.5 . . ?
C2A N2A H21A 120.0 . . ?
C2A N2A H22A 120.0 . . ?
H21A N2A H22A 120.0 . . ?
C6B N1B C2B 122.6(7) . . ?
C6B N1B H1B 118.7 . . ?
C2B N1B H1B 118.7 . . ?
N2B C2B N1B 118.7(7) . . ?
N2B C2B C3B 123.5(7) . . ?
N1B C2B C3B 117.9(7) . . ?
C4B C3B C2B 119.8(8) . . ?
C4B C3B H3B 120.1 . . ?
C2B C3B H3B 120.1 . . ?
C3B C4B C5B 120.4(8) . . ?
C3B C4B H4B 119.8 . . ?
C5B C4B H4B 119.8 . . ?
C6B C5B C4B 118.5(8) . . ?
C6B C5B H5B 120.8 . . ?
C4B C5B H5B 120.8 . . ?
N1B C6B C5B 120.9(8) . . ?
N1B C6B H6B 119.5 . . ?
C5B C6B H6B 119.5 . . ?
C2B N2B H21B 120.0 . . ?
C2B N2B H22B 120.0 . . ?
H21B N2B H22B 120.0 . . ?
O1C C1C C2C 125.3(7) . . ?
O1C C1C C6C 120.1(7) . . ?
C2C C1C C6C 114.6(6) . . ?
C3C C2C C1C 123.0(7) . . ?
C3C C2C N1C 116.0(8) . . ?
C1C C2C N1C 121.0(7) . . ?
C2C C3C C4C 120.9(8) . . ?
C2C C3C H3C 119.6 . . ?
C4C C3C H3C 119.6 . . ?
C3C C4C C5C 116.6(7) . . ?
C3C C4C H4C 121.7 . . ?
C5C C4C H4C 121.7 . . ?
C6C C5C C4C 124.9(7) . . ?
C6C C5C N2C 117.9(7) . . ?
C4C C5C N2C 117.1(7) . . ?
C5C C6C C1C 120.0(7) . . ?
C5C C6C H6C 120.0 . . ?
C1C C6C H6C 120.0 . . ?
O3C N1C O2C 121.6(7) . . ?
O3C N1C C2C 118.5(7) . . ?
O2C N1C C2C 119.9(7) . . ?
O4C N2C O5C 123.5(6) . . ?
O4C N2C C5C 118.7(7) . . ?
O5C N2C C5C 117.8(7) . . ?
O1D C1D C2D 126.2(7) . . ?
O1D C1D C6D 119.3(7) . . ?
C2D C1D C6D 114.5(7) . . ?
C3D C2D C1D 123.0(7) . . ?
C3D C2D N1D 117.2(7) . . ?
C1D C2D N1D 119.8(7) . . ?
C4D C3D C2D 121.2(8) . . ?
C4D C3D H3D 119.4 . . ?
C2D C3D H3D 119.4 . . ?
C3D C4D C5D 116.3(7) . . ?
C3D C4D H4D 121.8 . . ?
C5D C4D H4D 121.8 . . ?
C6D C5D C4D 124.9(7) . . ?
C6D C5D N2D 117.4(7) . . ?
C4D C5D N2D 117.8(7) . . ?
C5D C6D C1D 120.0(7) . . ?
C5D C6D H6D 120.0 . . ?
C1D C6D H6D 120.0 . . ?
O2D N1D O3D 121.2(6) . . ?
O2D N1D C2D 120.7(7) . . ?
O3D N1D C2D 118.0(6) . . ?
O5D N2D O4D 124.1(7) . . ?
O5D N2D C5D 118.5(7) . . ?
O4D N2D C5D 117.4(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
C6A N1A C2A N2A 178.4(8) . . . . ?
C6A N1A C2A C3A -1.0(12) . . . . ?
N2A C2A C3A C4A -177.6(8) . . . . ?
N1A C2A C3A C4A 1.7(11) . . . . ?
C2A C3A C4A C5A -1.0(12) . . . . ?
C3A C4A C5A C6A -0.5(13) . . . . ?
C2A N1A C6A C5A -0.5(13) . . . . ?
C4A C5A C6A N1A 1.3(13) . . . . ?
C6B N1B C2B N2B -179.7(7) . . . . ?
C6B N1B C2B C3B 0.4(12) . . . . ?
N2B C2B C3B C4B 179.9(8) . . . . ?
N1B C2B C3B C4B -0.3(12) . . . . ?
C2B C3B C4B C5B 0.0(13) . . . . ?
C3B C4B C5B C6B 0.1(12) . . . . ?
C2B N1B C6B C5B -0.3(12) . . . . ?
C4B C5B C6B N1B 0.1(12) . . . . ?
O1C C1C C2C C3C -179.4(9) . . . . ?
C6C C1C C2C C3C 2.5(12) . . . . ?
O1C C1C C2C N1C 0.9(13) . . . . ?
C6C C1C C2C N1C -177.2(7) . . . . ?
C1C C2C C3C C4C -1.7(13) . . . . ?
N1C C2C C3C C4C 178.0(8) . . . . ?
C2C C3C C4C C5C 0.8(13) . . . . ?
C3C C4C C5C C6C -0.9(13) . . . . ?
C3C C4C C5C N2C 178.4(7) . . . . ?
C4C C5C C6C C1C 1.9(13) . . . . ?
N2C C5C C6C C1C -177.4(7) . . . . ?
O1C C1C C6C C5C 179.3(8) . . . . ?
C2C C1C C6C C5C -2.5(12) . . . . ?
C3C C2C N1C O3C -3.2(11) . . . . ?
C1C C2C N1C O3C 176.5(8) . . . . ?
C3C C2C N1C O2C 175.4(8) . . . . ?
C1C C2C N1C O2C -4.9(12) . . . . ?
C6C C5C N2C O4C -172.0(8) . . . . ?
C4C C5C N2C O4C 8.6(11) . . . . ?
C6C C5C N2C O5C 6.8(11) . . . . ?
C4C C5C N2C O5C -172.6(7) . . . . ?
O1D C1D C2D C3D 178.5(9) . . . . ?
C6D C1D C2D C3D 0.2(12) . . . . ?
O1D C1D C2D N1D -3.0(14) . . . . ?
C6D C1D C2D N1D 178.8(7) . . . . ?
C1D C2D C3D C4D -0.2(13) . . . . ?
N1D C2D C3D C4D -178.8(8) . . . . ?
C2D C3D C4D C5D 0.4(12) . . . . ?
C3D C4D C5D C6D -0.8(13) . . . . ?
C3D C4D C5D N2D 179.4(7) . . . . ?
C4D C5D C6D C1D 0.9(13) . . . . ?
N2D C5D C6D C1D -179.3(8) . . . . ?
O1D C1D C6D C5D -178.9(8) . . . . ?
C2D C1D C6D C5D -0.6(12) . . . . ?
C3D C2D N1D O2D -175.1(7) . . . . ?
C1D C2D N1D O2D 6.3(12) . . . . ?
C3D C2D N1D O3D 6.7(11) . . . . ?
C1D C2D N1D O3D -171.9(8) . . . . ?
C6D C5D N2D O5D -7.3(12) . . . . ?
C4D C5D N2D O5D 172.5(8) . . . . ?
C6D C5D N2D O4D 172.1(8) . . . . ?
C4D C5D N2D O4D -8.1(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
_geom_hbond_publ_flag
N1A H1A O1C 0.88 1.81 2.595(9) 147.8 . yes
N2A H21A O1C 0.88 2.06 2.780(9) 138.6 . yes
N2A H21A O2C 0.88 2.34 3.103(8) 145.0 . yes
N2A H22A O2D 0.88 2.25 3.085(8) 158.6 . yes
N1B H1B O1D 0.88 1.85 2.639(9) 147.8 . yes
N2B H21B O1D 0.88 2.12 2.835(8) 137.7 . yes
N2B H21B O2D 0.88 2.27 3.033(8) 144.7 . yes
N2B H22B O2C 0.88 2.18 3.030(8) 161.2 . yes
C3A H3A O3D 0.95 2.56 3.431(10) 153.0 . yes
C6A H6A O4D 0.95 2.57 3.320(10) 135.8 3_445 yes
C6A H6A O5D 0.95 2.60 3.341(10) 135.2 3_455 yes
C3B H3B O3C 0.95 2.47 3.371(10) 159.3 . yes
C4B H4B O3D 0.95 2.45 3.206(10) 136.4 4_665 yes
C6B H6B O4C 0.95 2.42 3.219(10) 141.8 3_565 yes
C4D H4D O3C 0.95 2.64 3.408(10) 137.8 4_644 yes
C6D H6D O5C 0.95 2.63 3.518(10) 155.1 3 yes

_refine_diff_density_max         0.344
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.077


# start Validation Reply Form

_vrf_PLAT915_2ap6f1              
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         21 %     
RESPONSE: The reliable determination of the  absolute structure of 
a non-centrosymmetric crystal structure could not be determined; 
because there are no heavy atoms in the molecules.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_35l4chfa
_database_code_depnum_ccdc_archive 'CCDC 1991578'
loop_
_audit_author_name
_audit_author_address
'Iwona Bryndal'
;Department of Drugs Technology, Faculty of Pharmacy, Wroclaw Medical University
Poland
;
_audit_update_record             
;
2020-03-19 deposited with the CCDC.	2020-06-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        
'3,5-dimethylpyridine 2,3,5,6-tetrachlorophenol'
_chemical_name_common            
'3,5-dimethylpyridine 2,3,5,6-tetrachlorophenol'
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H2 Cl4 O, C7 H9 N'
_chemical_formula_sum            'C13 H11 Cl4 N O'
_chemical_formula_weight         339.03

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           9
_space_group_name_H-M_alt        'C 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'

_cell_length_a                   16.428(3)
_cell_length_b                   6.0198(12)
_cell_length_c                   14.604(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.02(2)
_cell_angle_gamma                90
_cell_volume                     1422.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5060
_cell_measurement_theta_min      2.827
_cell_measurement_theta_max      30.560

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.821
_shelx_estimated_absorpt_T_min   0.704
_shelx_estimated_absorpt_T_max   0.791
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.742
_exptl_absorpt_correction_T_max  0.813
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_detector_area_resol_mean 10.3456
_diffrn_reflns_number            5393
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_av_R_equivalents  0.0105
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.833
_diffrn_reflns_theta_max         30.628
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.912
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.582
_diffrn_reflns_point_group_measured_fraction_full 0.674
_reflns_number_total             2572
_reflns_number_gt                2569
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.275
_reflns_Friedel_fraction_max     0.251
_reflns_Friedel_fraction_full    0.348

_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2015)'
_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)+(0.0307P)²+0.3648P] 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 550 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2572
_refine_ls_number_parameters     175
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0174
_refine_ls_R_factor_gt           0.0174
_refine_ls_wR_factor_ref         0.0483
_refine_ls_wR_factor_gt          0.0483
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1B O 0.20118(8) 0.6907(2) 0.23116(8) 0.0170(2) Uani 1 1 d . . . . .
H1B H 0.242061 0.740709 0.210306 0.026 Uiso 1 1 calc R U . . .
C1B C 0.22294(11) 0.5052(3) 0.27939(11) 0.0127(3) Uani 1 1 d . . . . .
C2B C 0.30483(10) 0.4416(3) 0.31307(11) 0.0128(3) Uani 1 1 d . . . . .
C3B C 0.32167(11) 0.2432(3) 0.36250(11) 0.0133(3) Uani 1 1 d . . . . .
C4B C 0.25842(11) 0.1074(3) 0.38127(12) 0.0143(3) Uani 1 1 d . . . . .
H4B H 0.270468 -0.026859 0.415098 0.017 Uiso 1 1 calc R U . . .
C5B C 0.17698(11) 0.1713(3) 0.34969(11) 0.0138(3) Uani 1 1 d . . . . .
C6B C 0.15937(10) 0.3670(3) 0.29920(11) 0.0129(3) Uani 1 1 d . . . . .
Cl2B Cl 0.38368(2) 0.61333(7) 0.29245(3) 0.01759(9) Uani 1 1 d . . . . .
Cl3B Cl 0.42257(2) 0.16365(7) 0.40254(3) 0.01887(9) Uani 1 1 d . . . . .
Cl5B Cl 0.09776(3) 0.00544(8) 0.37330(3) 0.01986(9) Uani 1 1 d . . . . .
Cl6B Cl 0.05834(2) 0.44533(8) 0.25921(3) 0.01822(9) Uani 1 1 d . . . . .
N1A N 0.27347(10) 0.9875(3) 0.14007(10) 0.0173(3) Uani 1 1 d . . . . .
C2A C 0.34772(12) 1.0659(3) 0.12862(12) 0.0174(3) Uani 1 1 d . . . . .
H2A H 0.395186 0.977930 0.150245 0.021 Uiso 1 1 calc R U . . .
C3A C 0.35881(11) 1.2691(3) 0.08677(12) 0.0177(3) Uani 1 1 d . . . . .
C4A C 0.28775(12) 1.3936(3) 0.05505(11) 0.0177(3) Uani 1 1 d . . . . .
H4A H 0.292579 1.533598 0.026407 0.021 Uiso 1 1 calc R U . . .
C5A C 0.20988(12) 1.3155(3) 0.06481(11) 0.0165(3) Uani 1 1 d . . . . .
C6A C 0.20672(11) 1.1105(3) 0.10829(12) 0.0167(3) Uani 1 1 d . . . . .
H6A H 0.154159 1.054949 0.115818 0.020 Uiso 1 1 calc R U . . .
C7A C 0.44363(13) 1.3491(4) 0.07663(15) 0.0251(4) Uani 1 1 d . . . . .
H71A H 0.485347 1.271438 0.121423 0.038 Uiso 1 1 calc R U . . .
H72A H 0.447705 1.509330 0.088485 0.038 Uiso 1 1 calc R U . . .
H73A H 0.453035 1.318705 0.013377 0.038 Uiso 1 1 calc R U . . .
C8A C 0.13220(13) 1.4462(4) 0.03080(13) 0.0223(4) Uani 1 1 d . . . . .
H81A H 0.118126 1.434679 -0.037046 0.033 Uiso 1 1 calc R U . . .
H82A H 0.141231 1.602456 0.048534 0.033 Uiso 1 1 calc R U . . .
H83A H 0.086760 1.386442 0.058823 0.033 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
O1B C1B 1.335(2) . ?
O1B H1B 0.8400 . ?
C1B C2B 1.403(2) . ?
C1B C6B 1.404(2) . ?
C2B C3B 1.398(2) . ?
C2B Cl2B 1.7243(17) . ?
C3B C4B 1.387(2) . ?
C3B Cl3B 1.7268(18) . ?
C4B C5B 1.391(2) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.393(2) . ?
C5B Cl5B 1.7221(17) . ?
C6B Cl6B 1.7265(17) . ?
N1A C6A 1.338(2) . ?
N1A C2A 1.345(2) . ?
C2A C3A 1.394(2) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.397(3) . ?
C3A C7A 1.506(3) . ?
C4A C5A 1.394(3) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.393(2) . ?
C5A C8A 1.508(3) . ?
C6A H6A 0.9500 . ?
C7A H71A 0.9800 . ?
C7A H72A 0.9800 . ?
C7A H73A 0.9800 . ?
C8A H81A 0.9800 . ?
C8A H82A 0.9800 . ?
C8A H83A 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
C1B O1B H1B 109.5 . . ?
O1B C1B C2B 124.44(16) . . ?
O1B C1B C6B 117.62(16) . . ?
C2B C1B C6B 117.92(15) . . ?
C3B C2B C1B 120.38(16) . . ?
C3B C2B Cl2B 121.01(13) . . ?
C1B C2B Cl2B 118.61(13) . . ?
C4B C3B C2B 121.20(16) . . ?
C4B C3B Cl3B 118.54(13) . . ?
C2B C3B Cl3B 120.26(14) . . ?
C3B C4B C5B 118.82(16) . . ?
C3B C4B H4B 120.6 . . ?
C5B C4B H4B 120.6 . . ?
C4B C5B C6B 120.55(15) . . ?
C4B C5B Cl5B 119.34(13) . . ?
C6B C5B Cl5B 120.11(13) . . ?
C5B C6B C1B 121.11(15) . . ?
C5B C6B Cl6B 120.59(13) . . ?
C1B C6B Cl6B 118.30(13) . . ?
C6A N1A C2A 117.96(16) . . ?
N1A C2A C3A 123.58(17) . . ?
N1A C2A H2A 118.2 . . ?
C3A C2A H2A 118.2 . . ?
C2A C3A C4A 116.82(17) . . ?
C2A C3A C7A 121.18(17) . . ?
C4A C3A C7A 122.00(17) . . ?
C5A C4A C3A 120.93(16) . . ?
C5A C4A H4A 119.5 . . ?
C3A C4A H4A 119.5 . . ?
C6A C5A C4A 116.97(16) . . ?
C6A C5A C8A 121.06(18) . . ?
C4A C5A C8A 121.97(17) . . ?
N1A C6A C5A 123.74(17) . . ?
N1A C6A H6A 118.1 . . ?
C5A C6A H6A 118.1 . . ?
C3A C7A H71A 109.5 . . ?
C3A C7A H72A 109.5 . . ?
H71A C7A H72A 109.5 . . ?
C3A C7A H73A 109.5 . . ?
H71A C7A H73A 109.5 . . ?
H72A C7A H73A 109.5 . . ?
C5A C8A H81A 109.5 . . ?
C5A C8A H82A 109.5 . . ?
H81A C8A H82A 109.5 . . ?
C5A C8A H83A 109.5 . . ?
H81A C8A H83A 109.5 . . ?
H82A C8A H83A 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
O1B C1B C2B C3B -179.60(15) . . . . ?
C6B C1B C2B C3B 1.7(2) . . . . ?
O1B C1B C2B Cl2B 0.6(2) . . . . ?
C6B C1B C2B Cl2B -178.08(12) . . . . ?
C1B C2B C3B C4B -1.5(2) . . . . ?
Cl2B C2B C3B C4B 178.35(13) . . . . ?
C1B C2B C3B Cl3B 179.15(13) . . . . ?
Cl2B C2B C3B Cl3B -1.0(2) . . . . ?
C2B C3B C4B C5B 0.2(2) . . . . ?
Cl3B C3B C4B C5B 179.61(13) . . . . ?
C3B C4B C5B C6B 0.7(2) . . . . ?
C3B C4B C5B Cl5B -179.47(13) . . . . ?
C4B C5B C6B C1B -0.4(2) . . . . ?
Cl5B C5B C6B C1B 179.78(13) . . . . ?
C4B C5B C6B Cl6B 179.50(13) . . . . ?
Cl5B C5B C6B Cl6B -0.3(2) . . . . ?
O1B C1B C6B C5B -179.58(15) . . . . ?
C2B C1B C6B C5B -0.8(2) . . . . ?
O1B C1B C6B Cl6B 0.5(2) . . . . ?
C2B C1B C6B Cl6B 179.28(12) . . . . ?
C6A N1A C2A C3A 0.9(3) . . . . ?
N1A C2A C3A C4A -0.5(3) . . . . ?
N1A C2A C3A C7A 179.47(17) . . . . ?
C2A C3A C4A C5A -0.4(3) . . . . ?
C7A C3A C4A C5A 179.67(16) . . . . ?
C3A C4A C5A C6A 0.7(2) . . . . ?
C3A C4A C5A C8A -179.74(16) . . . . ?
C2A N1A C6A C5A -0.5(3) . . . . ?
C4A C5A C6A N1A -0.3(3) . . . . ?
C8A C5A C6A N1A -179.83(17) . . . . ?

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
O1B H1B N1A 0.84 1.93 2.631(2) 140.8 . yes
C2A H2A Cl6B 0.95 2.88 3.720(2) 148.7 3 yes

_refine_diff_density_max         0.290
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.044


# start Validation Reply Form

_vrf_PLAT915_35l4chfa            
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         25 %     
RESPONSE: The reliable determination of the  absolute structure of 
a non-centrosymmetric crystal structure could not be determined; 
the full Ewald sphere was not measured.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_3k4chfba
_database_code_depnum_ccdc_archive 'CCDC 1991577'
loop_
_audit_author_name
_audit_author_address
'Iwona Bryndal'
;Department of Drugs Technology, Faculty of Pharmacy, Wroclaw Medical University
Poland
;
_audit_update_record             
;
2020-03-19 deposited with the CCDC.	2020-06-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        
'2,3,6-trimethylpyridinium 2,3,5,6-tetrachlorophenolate'
_chemical_name_common            
'2,3,6-trimethylpyridinium 2,3,5,6-tetrachlorophenolate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H Cl4 O, C8 H12 N'
_chemical_formula_sum            'C14 H13 Cl4 N O'
_chemical_formula_weight         353.05

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      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                   7.6730(18)
_cell_length_b                   15.707(3)
_cell_length_c                   24.892(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3000.0(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5780
_cell_measurement_theta_min      2.949
_cell_measurement_theta_max      30.528

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_F_000             1440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.410
_exptl_crystal_size_min          0.320
_exptl_absorpt_coefficient_mu    0.782
_shelx_estimated_absorpt_T_min   0.705
_shelx_estimated_absorpt_T_max   0.788
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.772
_exptl_absorpt_correction_T_max  0.826
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3456
_diffrn_reflns_number            11914
_diffrn_reflns_av_unetI/netI     0.0528
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.955
_diffrn_reflns_theta_max         30.597
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.917
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7676
_reflns_number_gt                6908
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.785
_reflns_Friedel_fraction_max     0.913
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0263P)²+0.8733P] 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 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.51(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         7676
_refine_ls_number_parameters     368
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.0836
_refine_ls_wR_factor_gt          0.0796
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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
O1C O 0.1631(3) 0.47108(16) 0.75231(9) 0.0181(5) Uani 1 1 d . . . . .
C1C C 0.0738(4) 0.4799(2) 0.79609(12) 0.0123(7) Uani 1 1 d . . . . .
C2C C 0.0106(4) 0.4073(2) 0.82472(13) 0.0123(6) Uani 1 1 d . . . . .
C3C C -0.0842(5) 0.4159(2) 0.87200(13) 0.0149(7) Uani 1 1 d . . . . .
C4C C -0.1232(5) 0.4950(2) 0.89347(13) 0.0156(7) Uani 1 1 d . . . . .
H4C H -0.188328 0.499882 0.925780 0.019 Uiso 1 1 calc R U . . .
C5C C -0.0645(5) 0.5669(2) 0.86652(13) 0.0139(7) Uani 1 1 d . . . . .
C6C C 0.0299(4) 0.5602(2) 0.81905(13) 0.0134(7) Uani 1 1 d . . . . .
Cl2C Cl 0.05910(11) 0.30763(5) 0.79907(3) 0.01742(18) Uani 1 1 d . . . . .
Cl3C Cl -0.15618(13) 0.32641(6) 0.90613(4) 0.0246(2) Uani 1 1 d . . . . .
Cl5C Cl -0.11856(12) 0.66573(6) 0.89252(3) 0.0229(2) Uani 1 1 d . . . . .
Cl6C Cl 0.09489(12) 0.65024(5) 0.78436(3) 0.02044(19) Uani 1 1 d . . . . .
O1D O 0.8340(3) 0.49548(15) 0.56011(9) 0.0164(5) Uani 1 1 d . . . . .
C1D C 0.9229(4) 0.4921(2) 0.51597(12) 0.0121(6) Uani 1 1 d . . . . .
C2D C 0.9664(4) 0.4152(2) 0.48916(13) 0.0136(7) Uani 1 1 d . . . . .
C3D C 1.0628(4) 0.4139(2) 0.44187(13) 0.0148(7) Uani 1 1 d . . . . .
C4D C 1.1226(5) 0.4883(2) 0.41869(13) 0.0155(7) Uani 1 1 d . . . . .
H4D H 1.188648 0.487087 0.386421 0.019 Uiso 1 1 calc R U . . .
C5D C 1.0835(5) 0.5654(2) 0.44389(13) 0.0144(7) Uani 1 1 d . . . . .
C6D C 0.9870(4) 0.5681(2) 0.49099(13) 0.0115(7) Uani 1 1 d . . . . .
Cl2D Cl 0.89653(12) 0.32092(5) 0.51862(3) 0.01915(18) Uani 1 1 d . . . . .
Cl3D Cl 1.11601(12) 0.31851(5) 0.41069(3) 0.02120(19) Uani 1 1 d . . . . .
Cl5D Cl 1.15985(12) 0.65827(6) 0.41437(3) 0.0227(2) Uani 1 1 d . . . . .
Cl6D Cl 0.93999(11) 0.66423(5) 0.52136(3) 0.01454(16) Uani 1 1 d . . . . .
N1A N 0.3868(4) 0.56349(18) 0.70333(11) 0.0151(6) Uani 1 1 d . . . . .
H1A H 0.302488 0.542038 0.723126 0.018 Uiso 1 1 calc R U . . .
C2A C 0.3494(5) 0.5863(2) 0.65223(13) 0.0155(7) Uani 1 1 d . . . . .
C3A C 0.4813(5) 0.6177(2) 0.61900(13) 0.0162(7) Uani 1 1 d . . . . .
C4A C 0.6479(4) 0.6253(2) 0.64121(14) 0.0166(7) Uani 1 1 d . . . . .
H4A H 0.740991 0.645253 0.619418 0.020 Uiso 1 1 calc R U . . .
C5A C 0.6801(5) 0.6043(2) 0.69430(14) 0.0201(8) Uani 1 1 d . . . . .
H5A H 0.793031 0.612064 0.709133 0.024 Uiso 1 1 calc R U . . .
C6A C 0.5465(5) 0.5718(2) 0.72571(14) 0.0174(7) Uani 1 1 d . . . . .
C7A C 0.1638(5) 0.5762(2) 0.63477(14) 0.0200(8) Uani 1 1 d . . . . .
H71A H 0.113791 0.632357 0.627153 0.030 Uiso 1 1 calc R U . . .
H72A H 0.096854 0.548669 0.663450 0.030 Uiso 1 1 calc R U . . .
H73A H 0.159144 0.541053 0.602282 0.030 Uiso 1 1 calc R U . . .
C8A C 0.4456(5) 0.6416(2) 0.56152(13) 0.0207(8) Uani 1 1 d . . . . .
H81A H 0.394172 0.698639 0.560187 0.031 Uiso 1 1 calc R U . . .
H82A H 0.364415 0.600439 0.545712 0.031 Uiso 1 1 calc R U . . .
H83A H 0.555024 0.641178 0.541208 0.031 Uiso 1 1 calc R U . . .
C9A C 0.5646(5) 0.5475(3) 0.78381(14) 0.0260(9) Uani 1 1 d . . . . .
H91A H 0.484350 0.500736 0.792030 0.039 Uiso 1 1 calc R U . . .
H92A H 0.536841 0.596645 0.806486 0.039 Uiso 1 1 calc R U . . .
H93A H 0.684599 0.529159 0.790820 0.039 Uiso 1 1 calc R U . . .
N1B N 0.6108(4) 0.40068(17) 0.60828(11) 0.0150(6) Uani 1 1 d . . . . .
H1B H 0.695375 0.422746 0.588879 0.018 Uiso 1 1 calc R U . . .
C2B C 0.6474(5) 0.3765(2) 0.65918(13) 0.0154(7) Uani 1 1 d . . . . .
C3B C 0.5157(5) 0.3441(2) 0.69179(14) 0.0187(7) Uani 1 1 d . . . . .
C4B C 0.3487(5) 0.3388(2) 0.66975(15) 0.0226(8) Uani 1 1 d . . . . .
H4B H 0.255072 0.318687 0.691265 0.027 Uiso 1 1 calc R U . . .
C5B C 0.3175(5) 0.3623(2) 0.61692(15) 0.0193(8) Uani 1 1 d . . . . .
H5B H 0.203552 0.357390 0.602298 0.023 Uiso 1 1 calc R U . . .
C6B C 0.4521(5) 0.3929(2) 0.58562(15) 0.0184(7) Uani 1 1 d . . . . .
C7B C 0.8339(5) 0.3863(3) 0.67669(15) 0.0220(8) Uani 1 1 d . . . . .
H71B H 0.899903 0.415712 0.648576 0.033 Uiso 1 1 calc R U . . .
H72B H 0.884839 0.329928 0.682952 0.033 Uiso 1 1 calc R U . . .
H73B H 0.838380 0.419560 0.709959 0.033 Uiso 1 1 calc R U . . .
C8B C 0.5516(5) 0.3144(3) 0.74824(14) 0.0266(9) Uani 1 1 d . . . . .
H81B H 0.609952 0.258898 0.747151 0.040 Uiso 1 1 calc R U . . .
H82B H 0.441338 0.309094 0.767854 0.040 Uiso 1 1 calc R U . . .
H83B H 0.626710 0.355737 0.766456 0.040 Uiso 1 1 calc R U . . .
C9B C 0.4353(5) 0.4164(3) 0.52748(14) 0.0247(8) Uani 1 1 d . . . . .
H91B H 0.459509 0.366396 0.505166 0.037 Uiso 1 1 calc R U . . .
H92B H 0.518837 0.461627 0.518875 0.037 Uiso 1 1 calc R U . . .
H93B H 0.316708 0.436623 0.520397 0.037 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
O1C C1C 1.295(4) . ?
C1C C6C 1.424(5) . ?
C1C C2C 1.429(5) . ?
C2C C3C 1.390(5) . ?
C2C Cl2C 1.731(3) . ?
C3C C4C 1.385(5) . ?
C3C Cl3C 1.733(3) . ?
C4C C5C 1.389(5) . ?
C4C H4C 0.9500 . ?
C5C C6C 1.390(5) . ?
C5C Cl5C 1.732(3) . ?
C6C Cl6C 1.731(3) . ?
O1D C1D 1.294(4) . ?
C1D C2D 1.420(4) . ?
C1D C6D 1.432(4) . ?
C2D C3D 1.390(5) . ?
C2D Cl2D 1.738(3) . ?
C3D C4D 1.382(5) . ?
C3D Cl3D 1.736(3) . ?
C4D C5D 1.395(5) . ?
C4D H4D 0.9500 . ?
C5D C6D 1.387(4) . ?
C5D Cl5D 1.736(3) . ?
C6D Cl6D 1.727(3) . ?
N1A C2A 1.352(4) . ?
N1A C6A 1.352(4) . ?
N1A H1A 0.8800 . ?
C2A C3A 1.397(5) . ?
C2A C7A 1.497(5) . ?
C3A C4A 1.398(5) . ?
C3A C8A 1.504(5) . ?
C4A C5A 1.384(5) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.386(5) . ?
C5A H5A 0.9500 . ?
C6A C9A 1.503(5) . ?
C7A H71A 0.9800 . ?
C7A H72A 0.9800 . ?
C7A H73A 0.9800 . ?
C8A H81A 0.9800 . ?
C8A H82A 0.9800 . ?
C8A H83A 0.9800 . ?
C9A H91A 0.9800 . ?
C9A H92A 0.9800 . ?
C9A H93A 0.9800 . ?
N1B C6B 1.347(4) . ?
N1B C2B 1.352(4) . ?
N1B H1B 0.8800 . ?
C2B C3B 1.392(5) . ?
C2B C7B 1.504(5) . ?
C3B C4B 1.396(5) . ?
C3B C8B 1.506(5) . ?
C4B C5B 1.387(5) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.381(5) . ?
C5B H5B 0.9500 . ?
C6B C9B 1.499(5) . ?
C7B H71B 0.9800 . ?
C7B H72B 0.9800 . ?
C7B H73B 0.9800 . ?
C8B H81B 0.9800 . ?
C8B H82B 0.9800 . ?
C8B H83B 0.9800 . ?
C9B H91B 0.9800 . ?
C9B H92B 0.9800 . ?
C9B H93B 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
O1C C1C C6C 123.9(3) . . ?
O1C C1C C2C 120.9(3) . . ?
C6C C1C C2C 115.2(3) . . ?
C3C C2C C1C 121.5(3) . . ?
C3C C2C Cl2C 120.8(3) . . ?
C1C C2C Cl2C 117.7(2) . . ?
C4C C3C C2C 121.8(3) . . ?
C4C C3C Cl3C 118.0(3) . . ?
C2C C3C Cl3C 120.2(3) . . ?
C3C C4C C5C 118.2(3) . . ?
C3C C4C H4C 120.9 . . ?
C5C C4C H4C 120.9 . . ?
C4C C5C C6C 121.1(3) . . ?
C4C C5C Cl5C 118.1(3) . . ?
C6C C5C Cl5C 120.7(3) . . ?
C5C C6C C1C 122.1(3) . . ?
C5C C6C Cl6C 120.8(3) . . ?
C1C C6C Cl6C 117.1(3) . . ?
O1D C1D C2D 123.9(3) . . ?
O1D C1D C6D 121.0(3) . . ?
C2D C1D C6D 115.1(3) . . ?
C3D C2D C1D 122.4(3) . . ?
C3D C2D Cl2D 120.6(3) . . ?
C1D C2D Cl2D 117.0(3) . . ?
C4D C3D C2D 121.2(3) . . ?
C4D C3D Cl3D 117.7(3) . . ?
C2D C3D Cl3D 121.1(3) . . ?
C3D C4D C5D 118.3(3) . . ?
C3D C4D H4D 120.8 . . ?
C5D C4D H4D 120.8 . . ?
C6D C5D C4D 121.4(3) . . ?
C6D C5D Cl5D 120.8(3) . . ?
C4D C5D Cl5D 117.8(3) . . ?
C5D C6D C1D 121.6(3) . . ?
C5D C6D Cl6D 120.6(3) . . ?
C1D C6D Cl6D 117.8(2) . . ?
C2A N1A C6A 123.6(3) . . ?
C2A N1A H1A 118.2 . . ?
C6A N1A H1A 118.2 . . ?
N1A C2A C3A 119.8(3) . . ?
N1A C2A C7A 116.5(3) . . ?
C3A C2A C7A 123.7(3) . . ?
C2A C3A C4A 117.3(3) . . ?
C2A C3A C8A 121.3(3) . . ?
C4A C3A C8A 121.4(3) . . ?
C5A C4A C3A 121.3(3) . . ?
C5A C4A H4A 119.3 . . ?
C3A C4A H4A 119.3 . . ?
C4A C5A C6A 119.6(3) . . ?
C4A C5A H5A 120.2 . . ?
C6A C5A H5A 120.2 . . ?
N1A C6A C5A 118.3(3) . . ?
N1A C6A C9A 117.1(3) . . ?
C5A C6A C9A 124.6(3) . . ?
C2A C7A H71A 109.5 . . ?
C2A C7A H72A 109.5 . . ?
H71A C7A H72A 109.5 . . ?
C2A C7A H73A 109.5 . . ?
H71A C7A H73A 109.5 . . ?
H72A C7A H73A 109.5 . . ?
C3A C8A H81A 109.5 . . ?
C3A C8A H82A 109.5 . . ?
H81A C8A H82A 109.5 . . ?
C3A C8A H83A 109.5 . . ?
H81A C8A H83A 109.5 . . ?
H82A C8A H83A 109.5 . . ?
C6A C9A H91A 109.5 . . ?
C6A C9A H92A 109.5 . . ?
H91A C9A H92A 109.5 . . ?
C6A C9A H93A 109.5 . . ?
H91A C9A H93A 109.5 . . ?
H92A C9A H93A 109.5 . . ?
C6B N1B C2B 123.7(3) . . ?
C6B N1B H1B 118.2 . . ?
C2B N1B H1B 118.2 . . ?
N1B C2B C3B 119.9(3) . . ?
N1B C2B C7B 116.1(3) . . ?
C3B C2B C7B 124.0(3) . . ?
C2B C3B C4B 117.3(3) . . ?
C2B C3B C8B 121.6(3) . . ?
C4B C3B C8B 121.0(3) . . ?
C5B C4B C3B 121.0(3) . . ?
C5B C4B H4B 119.5 . . ?
C3B C4B H4B 119.5 . . ?
C6B C5B C4B 119.9(3) . . ?
C6B C5B H5B 120.0 . . ?
C4B C5B H5B 120.0 . . ?
N1B C6B C5B 118.1(3) . . ?
N1B C6B C9B 117.4(3) . . ?
C5B C6B C9B 124.5(3) . . ?
C2B C7B H71B 109.5 . . ?
C2B C7B H72B 109.5 . . ?
H71B C7B H72B 109.5 . . ?
C2B C7B H73B 109.5 . . ?
H71B C7B H73B 109.5 . . ?
H72B C7B H73B 109.5 . . ?
C3B C8B H81B 109.5 . . ?
C3B C8B H82B 109.5 . . ?
H81B C8B H82B 109.5 . . ?
C3B C8B H83B 109.5 . . ?
H81B C8B H83B 109.5 . . ?
H82B C8B H83B 109.5 . . ?
C6B C9B H91B 109.5 . . ?
C6B C9B H92B 109.5 . . ?
H91B C9B H92B 109.5 . . ?
C6B C9B H93B 109.5 . . ?
H91B C9B H93B 109.5 . . ?
H92B C9B H93B 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
O1C C1C C2C C3C 179.5(3) . . . . ?
C6C C1C C2C C3C -1.1(5) . . . . ?
O1C C1C C2C Cl2C 0.5(4) . . . . ?
C6C C1C C2C Cl2C 180.0(2) . . . . ?
C1C C2C C3C C4C 0.5(5) . . . . ?
Cl2C C2C C3C C4C 179.4(3) . . . . ?
C1C C2C C3C Cl3C -179.1(3) . . . . ?
Cl2C C2C C3C Cl3C -0.2(4) . . . . ?
C2C C3C C4C C5C -0.1(5) . . . . ?
Cl3C C3C C4C C5C 179.4(3) . . . . ?
C3C C4C C5C C6C 0.4(5) . . . . ?
C3C C4C C5C Cl5C 178.3(3) . . . . ?
C4C C5C C6C C1C -1.1(5) . . . . ?
Cl5C C5C C6C C1C -178.9(3) . . . . ?
C4C C5C C6C Cl6C 177.4(3) . . . . ?
Cl5C C5C C6C Cl6C -0.4(4) . . . . ?
O1C C1C C6C C5C -179.2(3) . . . . ?
C2C C1C C6C C5C 1.3(5) . . . . ?
O1C C1C C6C Cl6C 2.3(5) . . . . ?
C2C C1C C6C Cl6C -177.2(2) . . . . ?
O1D C1D C2D C3D -179.7(3) . . . . ?
C6D C1D C2D C3D -0.5(5) . . . . ?
O1D C1D C2D Cl2D -0.7(5) . . . . ?
C6D C1D C2D Cl2D 178.5(2) . . . . ?
C1D C2D C3D C4D 0.5(5) . . . . ?
Cl2D C2D C3D C4D -178.5(3) . . . . ?
C1D C2D C3D Cl3D 179.1(3) . . . . ?
Cl2D C2D C3D Cl3D 0.2(4) . . . . ?
C2D C3D C4D C5D -0.1(5) . . . . ?
Cl3D C3D C4D C5D -178.9(3) . . . . ?
C3D C4D C5D C6D -0.1(5) . . . . ?
C3D C4D C5D Cl5D 179.9(3) . . . . ?
C4D C5D C6D C1D 0.0(5) . . . . ?
Cl5D C5D C6D C1D -180.0(3) . . . . ?
C4D C5D C6D Cl6D -179.9(3) . . . . ?
Cl5D C5D C6D Cl6D 0.2(4) . . . . ?
O1D C1D C6D C5D 179.5(3) . . . . ?
C2D C1D C6D C5D 0.3(5) . . . . ?
O1D C1D C6D Cl6D -0.6(4) . . . . ?
C2D C1D C6D Cl6D -179.8(2) . . . . ?
C6A N1A C2A C3A 2.3(5) . . . . ?
C6A N1A C2A C7A -177.4(3) . . . . ?
N1A C2A C3A C4A -1.0(5) . . . . ?
C7A C2A C3A C4A 178.6(3) . . . . ?
N1A C2A C3A C8A 178.4(3) . . . . ?
C7A C2A C3A C8A -2.0(5) . . . . ?
C2A C3A C4A C5A -1.4(5) . . . . ?
C8A C3A C4A C5A 179.2(3) . . . . ?
C3A C4A C5A C6A 2.6(5) . . . . ?
C2A N1A C6A C5A -1.1(5) . . . . ?
C2A N1A C6A C9A 177.1(3) . . . . ?
C4A C5A C6A N1A -1.4(5) . . . . ?
C4A C5A C6A C9A -179.4(4) . . . . ?
C6B N1B C2B C3B -2.3(5) . . . . ?
C6B N1B C2B C7B 177.3(3) . . . . ?
N1B C2B C3B C4B -0.4(5) . . . . ?
C7B C2B C3B C4B -179.9(3) . . . . ?
N1B C2B C3B C8B 178.5(3) . . . . ?
C7B C2B C3B C8B -1.1(5) . . . . ?
C2B C3B C4B C5B 2.0(5) . . . . ?
C8B C3B C4B C5B -176.9(4) . . . . ?
C3B C4B C5B C6B -1.1(6) . . . . ?
C2B N1B C6B C5B 3.2(5) . . . . ?
C2B N1B C6B C9B -175.4(3) . . . . ?
C4B C5B C6B N1B -1.5(5) . . . . ?
C4B C5B C6B C9B 177.1(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
_geom_hbond_publ_flag
N1A H1A O1C 0.88 1.71 2.557(4) 161.6 . yes
N1A H1A Cl6C 0.88 2.78 3.308(3) 119.6 . yes
C7A H72A O1C 0.98 2.58 3.360(4) 137.0 . yes
N1B H1B O1D 0.88 1.72 2.567(4) 161.4 . yes
N1B H1B Cl2D 0.88 2.83 3.370(3) 121.3 . yes
C7B H71B O1D 0.98 2.58 3.371(4) 137.4 . yes
C7B H72B Cl6C 0.98 2.94 3.871(4) 158.7 3_646 yes

_refine_diff_density_max         0.552
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.077

####################################################################### 
# 
# 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_2appnf
_database_code_depnum_ccdc_archive 'CCDC 1991576'
loop_
_audit_author_name
_audit_author_address
'Iwona Bryndal'
;Department of Drugs Technology, Faculty of Pharmacy, Wroclaw Medical University
Poland
;
_audit_update_record             
;
2020-03-19 deposited with the CCDC.	2020-06-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        
'2-aminopyridinium 4-nitrophenolate 4-nitrophenol'
_chemical_name_common            
'2-aminopyridinium 4-nitrophenolate 4-nitrophenol'
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H4 N O3, C6 H5 N O3, C5 H7 N2'
_chemical_formula_sum            'C17 H16 N4 O6'
_chemical_formula_weight         372.34

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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -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, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   13.249(5)
_cell_length_b                   10.910(4)
_cell_length_c                   11.697(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1690.8(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1798
_cell_measurement_theta_min      2.974
_cell_measurement_theta_max      28.729

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.113
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.3359
_diffrn_reflns_number            7309
_diffrn_reflns_av_unetI/netI     0.1088
_diffrn_reflns_av_R_equivalents  0.0748
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.980
_diffrn_reflns_theta_max         28.793
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.720
_diffrn_reflns_point_group_measured_fraction_full 0.773
_reflns_number_total             3160
_reflns_number_gt                1975
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.458
_reflns_Friedel_fraction_max     0.475
_reflns_Friedel_fraction_full    0.527

_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       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2015)'
_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)+(0.0600P)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 389 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.8(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3160
_refine_ls_number_parameters     261
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1131
_refine_ls_R_factor_gt           0.0671
_refine_ls_wR_factor_ref         0.1643
_refine_ls_wR_factor_gt          0.1349
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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
O1D O 0.6703(3) 0.2053(3) 0.4460(4) 0.0316(9) Uani 1 1 d . . . . .
H1D H 0.647550 0.267461 0.479687 0.047 Uiso 1 1 calc R U . . .
C1D C 0.7585(4) 0.2340(5) 0.3940(5) 0.0267(12) Uani 1 1 d . . . . .
C2D C 0.8212(4) 0.1406(5) 0.3608(5) 0.0269(12) Uani 1 1 d . . . . .
H2D H 0.801258 0.058031 0.373241 0.032 Uiso 1 1 calc R U . . .
C3D C 0.9131(4) 0.1648(4) 0.3094(5) 0.0264(12) Uani 1 1 d . . . . .
H3D H 0.956913 0.099960 0.287476 0.032 Uiso 1 1 calc R U . . .
C4D C 0.9398(4) 0.2861(5) 0.2906(5) 0.0256(12) Uani 1 1 d . . . . .
C5D C 0.8760(4) 0.3817(5) 0.3209(5) 0.0271(12) Uani 1 1 d . . . . .
H5D H 0.894660 0.464037 0.305125 0.033 Uiso 1 1 calc R U . . .
C6D C 0.7857(4) 0.3566(5) 0.3738(5) 0.0262(12) Uani 1 1 d . . . . .
H6D H 0.742162 0.421356 0.396368 0.031 Uiso 1 1 calc R U . . .
N1D N 1.0344(3) 0.3131(4) 0.2350(4) 0.0323(11) Uani 1 1 d . . . . .
O2D O 1.0877(3) 0.2283(3) 0.2005(4) 0.0365(10) Uani 1 1 d . . . . .
O3D O 1.0589(3) 0.4224(3) 0.2233(4) 0.0465(12) Uani 1 1 d . . . . .
O1C O 0.5706(3) 0.3913(3) 0.5218(4) 0.0311(9) Uani 1 1 d . . . . .
C1C C 0.4899(4) 0.3565(5) 0.5805(5) 0.0268(12) Uani 1 1 d . . . . .
C2C C 0.4686(4) 0.2311(5) 0.5995(5) 0.0301(13) Uani 1 1 d . . . . .
H2C H 0.515184 0.170840 0.573779 0.036 Uiso 1 1 calc R U . . .
C3C C 0.3827(4) 0.1950(5) 0.6539(5) 0.0285(12) Uani 1 1 d . . . . .
H3C H 0.369324 0.110238 0.664976 0.034 Uiso 1 1 calc R U . . .
C4C C 0.3150(4) 0.2819(4) 0.6931(5) 0.0252(11) Uani 1 1 d . . . . .
C5C C 0.3338(4) 0.4064(4) 0.6795(4) 0.0264(12) Uani 1 1 d . . . . .
H5C H 0.287731 0.465383 0.708452 0.032 Uiso 1 1 calc R U . . .
C6C C 0.4203(4) 0.4433(5) 0.6234(5) 0.0295(12) Uani 1 1 d . . . . .
H6C H 0.433202 0.528268 0.613403 0.035 Uiso 1 1 calc R U . . .
N1C N 0.2247(4) 0.2453(4) 0.7511(4) 0.0294(10) Uani 1 1 d . . . . .
O2C O 0.2023(3) 0.1330(3) 0.7531(4) 0.0344(10) Uani 1 1 d . . . . .
O3C O 0.1712(3) 0.3226(4) 0.7989(4) 0.0388(11) Uani 1 1 d . . . . .
N1A N 0.5926(5) 0.6274(6) 0.4888(6) 0.0246(15) Uani 0.815(11) 1 d . . P A 1
H1A H 0.577536 0.548936 0.492225 0.030 Uiso 0.815(11) 1 calc R U P A 1
C2A C 0.6795(6) 0.6666(7) 0.5369(7) 0.0226(16) Uani 0.815(11) 1 d D . P A 1
C3A C 0.7039(7) 0.7923(6) 0.5318(9) 0.0282(17) Uani 0.815(11) 1 d . . P A 1
H3A H 0.764956 0.822451 0.563883 0.034 Uiso 0.815(11) 1 calc R U P A 1
C4A C 0.6369(8) 0.8697(7) 0.4791(11) 0.030(2) Uani 0.815(11) 1 d . . P A 1
H4A H 0.651915 0.954785 0.475308 0.036 Uiso 0.815(11) 1 calc R U P A 1
C5A C 0.5474(8) 0.8268(9) 0.4309(9) 0.034(2) Uani 0.815(11) 1 d . . P A 1
H5A H 0.501250 0.881851 0.395825 0.041 Uiso 0.815(11) 1 calc R U P A 1
C6A C 0.5274(7) 0.7053(8) 0.4350(8) 0.0305(18) Uani 0.815(11) 1 d . . P A 1
H6A H 0.468447 0.672063 0.400582 0.037 Uiso 0.815(11) 1 d R U P A 1
N2A N 0.7415(4) 0.5869(4) 0.5856(5) 0.0261(15) Uani 0.815(11) 1 d D . P A 1
H21A H 0.726012 0.508430 0.586583 0.031 Uiso 0.815(11) 1 calc R U P A 1
H22A H 0.798069 0.612345 0.616988 0.031 Uiso 0.815(11) 1 calc R U P A 1
N1B N 0.625(3) 0.629(2) 0.507(3) 0.0246(15) Uani 0.185(11) 1 d G . P A 2
H1B H 0.625959 0.548489 0.511267 0.030 Uiso 0.185(11) 1 calc R U P A 2
C2B C 0.542(2) 0.689(4) 0.461(3) 0.0305(18) Uani 0.185(11) 1 d DG . P A 2
C3B C 0.542(3) 0.816(4) 0.453(5) 0.034(2) Uani 0.185(11) 1 d G . P A 2
H3B H 0.484827 0.857302 0.421900 0.041 Uiso 0.185(11) 1 calc R U P A 2
C4B C 0.624(4) 0.883(2) 0.492(5) 0.030(2) Uani 0.185(11) 1 d G . P A 2
H4B H 0.623509 0.970231 0.487098 0.036 Uiso 0.185(11) 1 calc R U P A 2
C5B C 0.707(3) 0.823(3) 0.538(5) 0.0282(17) Uani 0.185(11) 1 d G . P A 2
H5B H 0.763435 0.869089 0.564564 0.034 Uiso 0.185(11) 1 calc R U P A 2
C6B C 0.7079(19) 0.696(3) 0.545(3) 0.0226(16) Uani 0.185(11) 1 d G . P A 2
H6B H 0.764680 0.655016 0.576833 0.027 Uiso 0.185(11) 1 calc R U P A 2
N2B N 0.470(2) 0.629(3) 0.409(2) 0.055(10) Uani 0.185(11) 1 d D . P A 2
H21B H 0.472680 0.548791 0.402148 0.066 Uiso 0.185(11) 1 calc R U P A 2
H22B H 0.417683 0.669206 0.380122 0.066 Uiso 0.185(11) 1 calc R U P A 2


_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
O1D C1D 1.354(6) . ?
O1D H1D 0.8400 . ?
C1D C2D 1.371(7) . ?
C1D C6D 1.405(7) . ?
C2D C3D 1.384(7) . ?
C2D H2D 0.9500 . ?
C3D C4D 1.387(7) . ?
C3D H3D 0.9500 . ?
C4D C5D 1.388(7) . ?
C4D N1D 1.444(6) . ?
C5D C6D 1.374(8) . ?
C5D H5D 0.9500 . ?
C6D H6D 0.9500 . ?
N1D O2D 1.231(5) . ?
N1D O3D 1.244(5) . ?
O1C C1C 1.326(6) . ?
C1C C6C 1.414(7) . ?
C1C C2C 1.414(7) . ?
C2C C3C 1.363(7) . ?
C2C H2C 0.9500 . ?
C3C C4C 1.384(7) . ?
C3C H3C 0.9500 . ?
C4C C5C 1.390(7) . ?
C4C N1C 1.432(6) . ?
C5C C6C 1.380(7) . ?
C5C H5C 0.9500 . ?
C6C H6C 0.9500 . ?
N1C O3C 1.235(6) . ?
N1C O2C 1.262(5) . ?
N1A C2A 1.351(9) . ?
N1A C6A 1.365(9) . ?
N1A H1A 0.8800 . ?
C2A N2A 1.325(9) . ?
C2A C3A 1.410(9) . ?
C3A C4A 1.372(10) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.395(10) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.353(10) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
N2A H21A 0.8800 . ?
N2A H22A 0.8800 . ?
N1B C2B 1.3900 . ?
N1B C6B 1.3900 . ?
N1B H1B 0.8800 . ?
C2B N2B 1.316(15) . ?
C2B C3B 1.3900 . ?
C3B C4B 1.3900 . ?
C3B H3B 0.9500 . ?
C4B C5B 1.3900 . ?
C4B H4B 0.9500 . ?
C5B C6B 1.3900 . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
N2B H21B 0.8800 . ?
N2B H22B 0.8800 . ?

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
C1D O1D H1D 109.5 . . ?
O1D C1D C2D 118.6(5) . . ?
O1D C1D C6D 121.2(5) . . ?
C2D C1D C6D 120.3(5) . . ?
C1D C2D C3D 121.0(5) . . ?
C1D C2D H2D 119.5 . . ?
C3D C2D H2D 119.5 . . ?
C2D C3D C4D 118.3(5) . . ?
C2D C3D H3D 120.8 . . ?
C4D C3D H3D 120.8 . . ?
C3D C4D C5D 121.4(5) . . ?
C3D C4D N1D 119.1(5) . . ?
C5D C4D N1D 119.4(5) . . ?
C6D C5D C4D 119.7(5) . . ?
C6D C5D H5D 120.2 . . ?
C4D C5D H5D 120.2 . . ?
C5D C6D C1D 119.3(5) . . ?
C5D C6D H6D 120.4 . . ?
C1D C6D H6D 120.4 . . ?
O2D N1D O3D 122.3(5) . . ?
O2D N1D C4D 119.6(4) . . ?
O3D N1D C4D 118.1(5) . . ?
O1C C1C C6C 121.2(5) . . ?
O1C C1C C2C 121.3(5) . . ?
C6C C1C C2C 117.5(5) . . ?
C3C C2C C1C 121.3(5) . . ?
C3C C2C H2C 119.4 . . ?
C1C C2C H2C 119.4 . . ?
C2C C3C C4C 119.9(5) . . ?
C2C C3C H3C 120.1 . . ?
C4C C3C H3C 120.1 . . ?
C3C C4C C5C 121.0(5) . . ?
C3C C4C N1C 120.5(4) . . ?
C5C C4C N1C 118.5(5) . . ?
C6C C5C C4C 119.3(5) . . ?
C6C C5C H5C 120.4 . . ?
C4C C5C H5C 120.4 . . ?
C5C C6C C1C 121.0(5) . . ?
C5C C6C H6C 119.5 . . ?
C1C C6C H6C 119.5 . . ?
O3C N1C O2C 121.3(5) . . ?
O3C N1C C4C 120.2(4) . . ?
O2C N1C C4C 118.5(4) . . ?
C2A N1A C6A 122.3(5) . . ?
C2A N1A H1A 118.9 . . ?
C6A N1A H1A 118.9 . . ?
N2A C2A N1A 119.9(7) . . ?
N2A C2A C3A 120.9(7) . . ?
N1A C2A C3A 119.1(6) . . ?
C4A C3A C2A 118.0(6) . . ?
C4A C3A H3A 121.0 . . ?
C2A C3A H3A 121.0 . . ?
C3A C4A C5A 121.7(6) . . ?
C3A C4A H4A 119.2 . . ?
C5A C4A H4A 119.1 . . ?
C6A C5A C4A 118.8(7) . . ?
C6A C5A H5A 120.6 . . ?
C4A C5A H5A 120.6 . . ?
C5A C6A N1A 120.1(7) . . ?
C5A C6A H6A 121.3 . . ?
N1A C6A H6A 118.6 . . ?
C2A N2A H21A 120.0 . . ?
C2A N2A H22A 120.0 . . ?
H21A N2A H22A 120.0 . . ?
C2B N1B C6B 120.0 . . ?
C2B N1B H1B 120.0 . . ?
C6B N1B H1B 120.0 . . ?
N2B C2B N1B 122(3) . . ?
N2B C2B C3B 118(3) . . ?
N1B C2B C3B 120.0 . . ?
C4B C3B C2B 120.0 . . ?
C4B C3B H3B 120.0 . . ?
C2B C3B H3B 120.0 . . ?
C3B C4B C5B 120.0 . . ?
C3B C4B H4B 120.0 . . ?
C5B C4B H4B 120.0 . . ?
C6B C5B C4B 120.0 . . ?
C6B C5B H5B 120.0 . . ?
C4B C5B H5B 120.0 . . ?
C5B C6B N1B 120.0 . . ?
C5B C6B H6B 120.0 . . ?
N1B C6B H6B 120.0 . . ?
C2B N2B H21B 120.0 . . ?
C2B N2B H22B 120.0 . . ?
H21B N2B H22B 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
O1D C1D C2D C3D -178.7(5) . . . . ?
C6D C1D C2D C3D 1.5(8) . . . . ?
C1D C2D C3D C4D -0.9(8) . . . . ?
C2D C3D C4D C5D -0.8(8) . . . . ?
C2D C3D C4D N1D -178.7(5) . . . . ?
C3D C4D C5D C6D 2.0(8) . . . . ?
N1D C4D C5D C6D 179.9(5) . . . . ?
C4D C5D C6D C1D -1.4(8) . . . . ?
O1D C1D C6D C5D 179.9(5) . . . . ?
C2D C1D C6D C5D -0.3(8) . . . . ?
C3D C4D N1D O2D 3.3(8) . . . . ?
C5D C4D N1D O2D -174.7(5) . . . . ?
C3D C4D N1D O3D -177.0(5) . . . . ?
C5D C4D N1D O3D 5.0(8) . . . . ?
O1C C1C C2C C3C -176.1(5) . . . . ?
C6C C1C C2C C3C 2.0(8) . . . . ?
C1C C2C C3C C4C -0.8(9) . . . . ?
C2C C3C C4C C5C -1.0(8) . . . . ?
C2C C3C C4C N1C -179.6(5) . . . . ?
C3C C4C C5C C6C 1.7(8) . . . . ?
N1C C4C C5C C6C -179.8(5) . . . . ?
C4C C5C C6C C1C -0.4(8) . . . . ?
O1C C1C C6C C5C 176.8(5) . . . . ?
C2C C1C C6C C5C -1.3(8) . . . . ?
C3C C4C N1C O3C 170.5(5) . . . . ?
C5C C4C N1C O3C -8.1(7) . . . . ?
C3C C4C N1C O2C -8.7(7) . . . . ?
C5C C4C N1C O2C 172.8(5) . . . . ?
C6A N1A C2A N2A -178.3(8) . . . . ?
C6A N1A C2A C3A 0.1(9) . . . . ?
N2A C2A C3A C4A 179.3(8) . . . . ?
N1A C2A C3A C4A 0.9(9) . . . . ?
C2A C3A C4A C5A -0.4(10) . . . . ?
C3A C4A C5A C6A -1.1(11) . . . . ?
C4A C5A C6A N1A 2.1(11) . . . . ?
C2A N1A C6A C5A -1.6(10) . . . . ?
C6B N1B C2B N2B 170(4) . . . . ?
C6B N1B C2B C3B 0.0 . . . . ?
N2B C2B C3B C4B -171(4) . . . . ?
N1B C2B C3B C4B 0.0 . . . . ?
C2B C3B C4B C5B 0.0 . . . . ?
C3B C4B C5B C6B 0.0 . . . . ?
C4B C5B C6B N1B 0.0 . . . . ?
C2B N1B C6B C5B 0.0 . . . . ?

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
O1D H1D O1C 0.84 1.76 2.579(5) 163.2 . yes
C2D H2D O2C 0.95 2.51 3.254(7) 134.9 2_654 yes
C5D H5D O3C 0.95 2.49 3.297(6) 143.1 2_664 yes
C3C H3C O3D 0.95 2.36 3.178(6) 144.0 4_645 yes
C6C H6C O2D 0.95 2.42 3.240(6) 143.8 4_655 yes
N1A^a H1A^a O1C 0.88 1.76 2.621(7) 166.7 . yes
N2A^a H21A^a O1C 0.88 2.54 3.199(7) 132.4 . yes
N2A^a H21A^a O2C 0.88 2.50 3.140(6) 129.7 3 yes
N2A^a H22A^a O2D 0.88 2.50 3.315(7) 153.8 2_765 yes
N2A^a H22A^a O3D 0.88 2.30 3.098(7) 151.2 2_765 yes
N1B^b H1B^b O1C 0.88 1.87 2.70(3) 156.5 . yes
C3B^b H3B^b O3C 0.95 2.55 3.35(4) 142.3 4_554 yes
N2B^b H22B^b N1C 0.88 2.55 3.41(3) 164.1 4_554 yes
N2B^b H22B^b O2C 0.88 2.21 2.91(3) 136.6 4_554 yes
N2B^b H22B^b O3C 0.88 2.26 3.10(3) 159.4 4_554 yes
N2B^b H21B^b O1C 0.88 2.57 3.21(3) 130.0 . yes

_refine_diff_density_max         0.323
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.072


# start Validation Reply Form
_vrf_PLAT915_2appnf              
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         47 %     
RESPONSE: The reliable determination of the  absolute structure of 
a non-centrosymmetric crystal structure could not be determined; 
because there are no heavy atoms in the molecules.
;
# end Validation Reply Form
