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#$Date: 2019-11-22 18:56:18 +0200 (Fri, 22 Nov 2019) $
#$Revision: 231235 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/63/4516307.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4516307
loop_
_publ_author_name
'Varughese, Sunil'
'Hoser, Anna A.'
'Jarzembska, Katarzyna N.'
'Pedireddi, V. R.'
'Woźniak, Krzysztof'
_publ_section_title
;
 Positional Isomerism and Conformational Flexibility Directed Structural
 Variations in the Molecular Complexes of Dihydroxybenzoic Acids
;
_journal_issue                   8
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3832
_journal_paper_doi               10.1021/acs.cgd.5b00471
_journal_volume                  15
_journal_year                    2015
_chemical_formula_sum            'C19 H16 N2 O4'
_chemical_formula_weight         336.34
_chemical_name_common            sv151
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                113.937(10)
_cell_angle_beta                 105.773(9)
_cell_angle_gamma                92.455(7)
_cell_formula_units_Z            2
_cell_length_a                   7.7094(7)
_cell_length_b                   10.5100(10)
_cell_length_c                   11.0988(12)
_cell_measurement_temperature    100(2)
_cell_volume                     778.92(16)
_computing_cell_refinement       CrysAlisRED
_computing_data_collection       CrysAlisCCD
_computing_data_reduction        CrysAlisRED
_computing_molecular_graphics    Diamond
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.6479
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  KM4CCD
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9227
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.79
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       planar
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.170
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         9227
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.170
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0562
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0782P)²+0.1682P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1721
_refine_ls_wR_factor_ref         0.1870
_reflns_number_gt                6163
_reflns_number_total             9227
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5b00471_si_003.cif
_cod_data_source_block           sv151
_cod_original_cell_volume        778.91(13)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4516307
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O2 O 0.38093(17) 0.22551(13) 0.74436(13) 0.0226(3) Uani 1 1 d .
O1 O 0.50189(17) 0.04285(13) 0.77286(13) 0.0239(3) Uani 1 1 d .
O3 O 0.15750(17) 0.17974(12) 0.50580(13) 0.0214(3) Uani 1 1 d .
O4 O -0.02537(17) -0.00507(13) 0.24225(13) 0.0232(3) Uani 1 1 d .
C1 C 0.3008(2) -0.00470(18) 0.55146(18) 0.0157(4) Uani 1 1 d .
C6 C 0.3279(2) -0.14547(19) 0.50185(18) 0.0168(4) Uani 1 1 d .
H6 H 0.4061 -0.1764 0.5603 0.020 Uiso 1 1 calc R
C2 C 0.1841(2) 0.04222(18) 0.46296(18) 0.0156(4) Uani 1 1 d .
C4 C 0.1173(2) -0.19338(18) 0.27474(18) 0.0165(4) Uani 1 1 d .
H4 H 0.0572 -0.2572 0.1829 0.020 Uiso 1 1 calc R
C7 C 0.3974(2) 0.0975(2) 0.69728(19) 0.0191(4) Uani 1 1 d .
C3 C 0.0898(2) -0.05571(19) 0.32279(19) 0.0173(4) Uani 1 1 d .
C5 C 0.2370(2) -0.23773(19) 0.3650(2) 0.0229(4) Uani 1 1 d .
H5 H 0.2552 -0.3311 0.3316 0.027 Uiso 1 1 calc R
N1B N 0.30614(19) 0.77881(15) 0.97641(15) 0.0183(4) Uani 1 1 d .
C10B C 0.1155(2) 0.59038(18) 0.69958(18) 0.0155(4) Uani 1 1 d .
C11B C 0.1862(2) 0.73112(18) 0.73634(19) 0.0182(4) Uani 1 1 d .
H11B H 0.1705 0.7643 0.6688 0.022 Uiso 1 1 calc R
C13B C 0.0163(2) 0.48682(18) 0.55543(18) 0.0181(4) Uani 1 1 d .
C9B C 0.1430(3) 0.5482(2) 0.8071(2) 0.0247(5) Uani 1 1 d .
H9B H 0.0980 0.4561 0.7877 0.030 Uiso 1 1 calc R
C12B C 0.2794(2) 0.81970(19) 0.87404(18) 0.0188(4) Uani 1 1 d .
H12B H 0.3259 0.9125 0.8968 0.023 Uiso 1 1 calc R
C8B C 0.2374(3) 0.6445(2) 0.9423(2) 0.0246(5) Uani 1 1 d .
H8B H 0.2540 0.6151 1.0126 0.029 Uiso 1 1 calc R
N1A N 0.20530(19) 0.20498(16) 0.02173(15) 0.0200(4) Uani 1 1 d .
C13A C 0.4972(2) 0.50569(18) 0.44178(18) 0.0163(4) Uani 1 1 d .
C10A C 0.3935(2) 0.40151(18) 0.29925(18) 0.0158(4) Uani 1 1 d .
C11A C 0.2898(2) 0.27333(18) 0.26808(19) 0.0186(4) Uani 1 1 d .
H11A H 0.2806 0.2505 0.3390 0.022 Uiso 1 1 calc R
C12A C 0.2012(2) 0.18103(19) 0.13107(19) 0.0203(4) Uani 1 1 d .
H12A H 0.1338 0.0961 0.1131 0.024 Uiso 1 1 calc R
C9A C 0.3968(2) 0.42836(19) 0.18625(19) 0.0197(4) Uani 1 1 d .
H9A H 0.4616 0.5130 0.2013 0.024 Uiso 1 1 calc R
C8A C 0.3038(2) 0.32917(19) 0.05209(19) 0.0219(4) Uani 1 1 d .
H8A H 0.3097 0.3493 -0.0211 0.026 Uiso 1 1 calc R
H1X H -0.0373 0.3957 0.5423 0.026(5) Uiso 1 1 d R
H2X H -0.0976 -0.0937 0.1308 0.074(8) Uiso 1 1 d R
H3X H 0.5676 0.5960 0.4475 0.024(5) Uiso 1 1 d R
H4X H 0.2283 0.2186 0.6100 0.037 Uiso 1 1 d R
H6X H 0.5683 0.1156 0.8625 0.037 Uiso 1 1 d R
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'
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
C7 O1 H6X 110.0 .
C2 O3 H4X 99.6 .
C3 O4 H2X 111.3 .
C6 C1 C2 120.46(16) .
C6 C1 C7 120.60(16) .
C2 C1 C7 118.93(15) .
C5 C6 C1 119.11(16) .
C5 C6 H6 120.4 .
C1 C6 H6 120.4 .
O3 C2 C1 122.49(15) .
O3 C2 C3 118.26(15) .
C1 C2 C3 119.25(16) .
C3 C4 C5 119.78(17) .
C3 C4 H4 120.1 .
C5 C4 H4 120.1 .
O2 C7 O1 123.15(16) .
O2 C7 C1 122.45(16) .
O1 C7 C1 114.41(15) .
O4 C3 C4 123.25(16) .
O4 C3 C2 116.76(15) .
C4 C3 C2 119.98(16) .
C6 C5 C4 121.39(17) .
C6 C5 H5 119.3 .
C4 C5 H5 119.3 .
C12B N1B C8B 117.78(15) .
C9B C10B C11B 117.19(16) .
C9B C10B C13B 119.32(16) .
C11B C10B C13B 123.48(16) .
C12B C11B C10B 119.22(17) .
C12B C11B H11B 120.4 .
C10B C11B H11B 120.4 .
C13B C13B C10B 125.1(2) 2_566
C13B C13B H1X 117.8 2_566
C10B C13B H1X 117.0 .
C8B C9B C10B 119.60(17) .
C8B C9B H9B 120.2 .
C10B C9B H9B 120.2 .
N1B C12B C11B 123.41(17) .
N1B C12B H12B 118.3 .
C11B C12B H12B 118.3 .
N1B C8B C9B 122.79(17) .
N1B C8B H8B 118.6 .
C9B C8B H8B 118.6 .
C12A N1A C8A 115.88(15) .
C13A C13A C10A 125.9(2) 2_666
C13A C13A H3X 119.9 2_666
C10A C13A H3X 114.2 .
C11A C10A C9A 116.47(16) .
C11A C10A C13A 123.62(16) .
C9A C10A C13A 119.91(16) .
C12A C11A C10A 119.34(17) .
C12A C11A H11A 120.3 .
C10A C11A H11A 120.3 .
N1A C12A C11A 124.67(17) .
N1A C12A H12A 117.7 .
C11A C12A H12A 117.7 .
C8A C9A C10A 120.11(16) .
C8A C9A H9A 119.9 .
C10A C9A H9A 119.9 .
N1A C8A C9A 123.52(17) .
N1A C8A H8A 118.2 .
C9A C8A H8A 118.2 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O2 C7 1.256(2) .
O1 C7 1.322(2) .
O1 H6X 0.9534 .
O3 C2 1.370(2) .
O3 H4X 1.0276 .
O4 C3 1.366(2) .
O4 H2X 1.1639 .
C1 C6 1.401(2) .
C1 C2 1.403(2) .
C1 C7 1.481(2) .
C6 C5 1.381(2) .
C6 H6 0.9300 .
C2 C3 1.425(2) .
C4 C3 1.373(2) .
C4 C5 1.409(2) .
C4 H4 0.9300 .
C5 H5 0.9300 .
N1B C12B 1.340(2) .
N1B C8B 1.346(2) .
C10B C9B 1.402(3) .
C10B C11B 1.404(2) .
C10B C13B 1.476(2) .
C11B C12B 1.382(2) .
C11B H11B 0.9300 .
C13B C13B 1.330(3) 2_566
C13B H1X 0.9638 .
C9B C8B 1.385(3) .
C9B H9B 0.9300 .
C12B H12B 0.9300 .
C8B H8B 0.9300 .
N1A C12A 1.343(2) .
N1A C8A 1.347(2) .
C13A C13A 1.335(3) 2_666
C13A C10A 1.474(2) .
C13A H3X 1.0432 .
C10A C11A 1.397(2) .
C10A C9A 1.399(3) .
C11A C12A 1.379(2) .
C11A H11A 0.9300 .
C12A H12A 0.9300 .
C9A C8A 1.383(2) .
C9A H9A 0.9300 .
C8A H8A 0.9300 .
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_4
C2 C1 C6 C5 -0.5(2) . .
C7 C1 C6 C5 -179.40(16) . .
C6 C1 C2 O3 -178.10(16) . .
C7 C1 C2 O3 0.8(2) . .
C6 C1 C2 C3 1.5(2) . .
C7 C1 C2 C3 -179.61(16) . .
C6 C1 C7 O2 177.79(16) . .
C2 C1 C7 O2 -1.1(2) . .
C6 C1 C7 O1 -2.1(2) . .
C2 C1 C7 O1 179.03(15) . .
C5 C4 C3 O4 -179.28(15) . .
C5 C4 C3 C2 0.9(3) . .
O3 C2 C3 O4 -1.9(2) . .
C1 C2 C3 O4 178.47(14) . .
O3 C2 C3 C4 177.96(15) . .
C1 C2 C3 C4 -1.7(2) . .
C1 C6 C5 C4 -0.3(3) . .
C3 C4 C5 C6 0.1(3) . .
C9B C10B C11B C12B 0.6(3) . .
C13B C10B C11B C12B -179.12(16) . .
C9B C10B C13B C13B -179.1(2) . 2_566
C11B C10B C13B C13B 0.6(3) . 2_566
C11B C10B C9B C8B -0.3(3) . .
C13B C10B C9B C8B 179.41(17) . .
C8B N1B C12B C11B -0.3(3) . .
C10B C11B C12B N1B -0.3(3) . .
C12B N1B C8B C9B 0.6(3) . .
C10B C9B C8B N1B -0.3(3) . .
C13A C13A C10A C11A -1.7(3) 2_666 .
C13A C13A C10A C9A 178.7(2) 2_666 .
C9A C10A C11A C12A 1.2(2) . .
C13A C10A C11A C12A -178.37(16) . .
C8A N1A C12A C11A -0.2(3) . .
C10A C11A C12A N1A -0.5(3) . .
C11A C10A C9A C8A -1.4(2) . .
C13A C10A C9A C8A 178.22(16) . .
C12A N1A C8A C9A 0.0(3) . .
C10A C9A C8A N1A 0.8(3) . .
