#------------------------------------------------------------------------------
#$Date: 2016-03-26 20:36:37 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180441 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/10/7211064.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_7211064
loop_
_publ_author_name
'Tao, Qian'
'Chen, Jia-Mei'
'Lu, Tong-Bu'
_publ_section_title
;
 Two polymorphs and one hydrate of a molecular salt involving
 phenazopyridine and salicylic acid
;
_journal_issue                   39
_journal_name_full               CrystEngComm
_journal_page_first              7852
_journal_paper_doi               10.1039/c3ce41188e
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C11 H12 N5, C7 H5 O3'
_chemical_formula_sum            'C18 H17 N5 O3'
_chemical_formula_weight         351.37
_chemical_name_common            phenazopyridine
_chemical_name_systematic
;
?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.498(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.7841(2)
_cell_length_b                   9.3170(3)
_cell_length_c                   18.9162(3)
_cell_measurement_reflns_used    1107
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      70.7855
_cell_measurement_theta_min      2.3360
_cell_volume                     842.36(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3140
_diffrn_reflns_theta_full        70.92
_diffrn_reflns_theta_max         70.92
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    0.809
_exptl_absorpt_correction_T_max  0.9235
_exptl_absorpt_correction_T_min  0.8883
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.5(5)
_refine_ls_extinction_coef       0.0032(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2233
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0537
_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)+(0.0896P)²+0.0754P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1438
_refine_ls_wR_factor_ref         0.1656
_reflns_number_gt                1841
_reflns_number_total             2233
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce41188e.txt
_cod_data_source_block           tq_5_110618
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7211064
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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
N2 N 0.2674(6) 0.4495(4) 0.22366(15) 0.0621(7) Uani 1 1 d .
N3 N 0.2617(7) 0.3673(5) 0.10983(16) 0.0778(9) Uani 1 1 d .
H2 H 0.1331 0.5061 0.2105 0.093 Uiso 1 1 d R
N1 N 0.2445(7) 0.5520(4) 0.33278(17) 0.0723(9) Uani 1 1 d .
H1B H 0.1153 0.6071 0.3151 0.087 Uiso 1 1 d R
H1A H 0.2969 0.5600 0.3767 0.087 Uiso 1 1 d R
H3B H 0.1296 0.4273 0.0999 0.087 Uiso 1 1 d R
H3A H 0.3227 0.3122 0.0773 0.087 Uiso 1 1 d R
N4 N 0.6954(6) 0.3495(4) 0.38387(16) 0.0643(8) Uani 1 1 d .
N5 N 0.6083(7) 0.4369(3) 0.42956(15) 0.0634(7) Uani 1 1 d .
C15 C 0.3626(7) 0.4547(4) 0.29228(18) 0.0595(8) Uani 1 1 d .
C16 C 0.5758(7) 0.3598(4) 0.31543(18) 0.0588(8) Uani 1 1 d .
C17 C 0.6825(8) 0.2652(5) 0.2653(2) 0.0686(9) Uani 1 1 d .
H17 H 0.8268 0.2004 0.2800 0.082 Uiso 1 1 calc R
C18 C 0.5869(8) 0.2629(5) 0.19664(19) 0.0693(10) Uani 1 1 d .
H18 H 0.6624 0.1976 0.1640 0.083 Uiso 1 1 calc R
C19 C 0.3720(8) 0.3601(4) 0.17469(18) 0.0621(8) Uani 1 1 d .
C20 C 0.7421(8) 0.4209(4) 0.49764(18) 0.0630(9) Uani 1 1 d .
C21 C 0.6502(9) 0.5091(5) 0.5505(2) 0.0714(10) Uani 1 1 d .
H21 H 0.5046 0.5762 0.5402 0.086 Uiso 1 1 calc R
C22 C 0.7674(10) 0.5005(6) 0.6174(2) 0.0807(12) Uani 1 1 d .
H22 H 0.7041 0.5628 0.6531 0.097 Uiso 1 1 calc R
C23 C 0.9759(10) 0.4027(5) 0.6340(2) 0.0770(11) Uani 1 1 d .
H23 H 1.0546 0.3964 0.6809 0.092 Uiso 1 1 calc R
C24 C 1.0689(9) 0.3141(5) 0.5817(2) 0.0769(11) Uani 1 1 d .
H24 H 1.2146 0.2473 0.5924 0.092 Uiso 1 1 calc R
C25 C 0.9521(8) 0.3217(5) 0.51422(19) 0.0700(10) Uani 1 1 d .
H25 H 1.0151 0.2590 0.4787 0.084 Uiso 1 1 calc R
O1 O -0.1641(7) 0.6394(4) 0.21708(16) 0.0925(10) Uani 1 1 d .
O2 O -0.1563(7) 0.5798(4) 0.10342(19) 0.0947(10) Uani 1 1 d .
O3 O -0.4624(9) 0.7055(4) 0.01266(16) 0.1000(11) Uani 1 1 d .
H4 H -0.3444 0.6492 0.0283 0.150 Uiso 1 1 d R
C1 C -0.2439(8) 0.6545(5) 0.1547(2) 0.0718(11) Uani 1 1 d .
C2 C -0.4687(7) 0.7629(5) 0.13637(18) 0.0620(9) Uani 1 1 d .
C3 C -0.5636(8) 0.7823(5) 0.06639(17) 0.0684(10) Uani 1 1 d .
C4 C -0.7673(11) 0.8866(6) 0.0500(2) 0.0865(13) Uani 1 1 d .
H4A H -0.8308 0.9004 0.0022 0.104 Uiso 1 1 calc R
C5 C -0.8745(11) 0.9679(6) 0.1016(3) 0.0862(12) Uani 1 1 d .
H5A H -1.0117 1.0388 0.0898 0.103 Uiso 1 1 calc R
C6 C -0.7854(11) 0.9480(6) 0.1704(3) 0.0879(12) Uani 1 1 d .
H6A H -0.8624 1.0039 0.2068 0.105 Uiso 1 1 calc R
C7 C -0.5865(9) 0.8481(5) 0.1868(2) 0.0737(11) Uani 1 1 d .
H7A H -0.5258 0.8364 0.2350 0.088 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C19 N2 C15 123.8(3)
N5 N4 C16 117.0(3)
N4 N5 C20 113.7(3)
N1 C15 N2 116.3(3)
N1 C15 C16 124.8(3)
N2 C15 C16 118.9(3)
N4 C16 C15 126.5(3)
N4 C16 C17 115.8(3)
C15 C16 C17 117.6(3)
C18 C17 C16 122.5(4)
C17 C18 C19 118.7(4)
N3 C19 N2 117.4(4)
N3 C19 C18 124.2(4)
N2 C19 C18 118.4(3)
C21 C20 C25 118.8(3)
C21 C20 N5 116.7(4)
C25 C20 N5 124.5(3)
C22 C21 C20 120.4(4)
C21 C22 C23 120.9(4)
C22 C23 C24 119.1(4)
C25 C24 C23 120.4(4)
C24 C25 C20 120.3(4)
O1 C1 O2 124.4(5)
O1 C1 C2 119.1(4)
O2 C1 C2 116.5(3)
C7 C2 C3 117.2(4)
C7 C2 C1 122.4(3)
C3 C2 C1 120.4(4)
O3 C3 C2 122.3(4)
O3 C3 C4 118.1(3)
C2 C3 C4 119.7(4)
C5 C4 C3 120.7(4)
C4 C5 C6 119.9(5)
C7 C6 C5 119.9(5)
C6 C7 C2 122.6(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N2 C19 1.357(5)
N2 C15 1.358(4)
N3 C19 1.316(5)
N1 C15 1.329(5)
N4 N5 1.271(4)
N4 C16 1.396(5)
N5 C20 1.421(5)
C15 C16 1.406(5)
C16 C17 1.407(5)
C17 C18 1.358(5)
C18 C19 1.418(6)
C20 C21 1.380(6)
C20 C25 1.391(6)
C21 C22 1.365(6)
C22 C23 1.377(7)
C23 C24 1.377(6)
C24 C25 1.372(6)
O1 C1 1.233(5)
O2 C1 1.279(6)
O3 C3 1.350(5)
C1 C2 1.505(6)
C2 C7 1.381(6)
C2 C3 1.392(5)
C3 C4 1.401(7)
C4 C5 1.353(7)
C5 C6 1.365(7)
C6 C7 1.357(7)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O1 0.86 1.90 2.717(5) 159.3 .
N1 H1B O1 0.86 2.26 2.983(4) 142.1 .
N3 H3B O2 0.86 1.98 2.813(5) 164.9 .
N3 H3A O3 0.86 2.11 2.959(5) 171.0 2_545
O3 H4 O2 0.82 1.77 2.499(5) 147.6 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C16 N4 N5 C20 -179.3(3)
C19 N2 C15 N1 177.6(3)
C19 N2 C15 C16 -2.1(5)
N5 N4 C16 C15 -1.9(5)
N5 N4 C16 C17 177.9(3)
N1 C15 C16 N4 1.1(6)
N2 C15 C16 N4 -179.2(3)
N1 C15 C16 C17 -178.7(4)
N2 C15 C16 C17 1.0(5)
N4 C16 C17 C18 -179.9(4)
C15 C16 C17 C18 -0.1(6)
C16 C17 C18 C19 0.2(6)
C15 N2 C19 N3 -179.3(3)
C15 N2 C19 C18 2.2(5)
C17 C18 C19 N3 -179.6(4)
C17 C18 C19 N2 -1.2(6)
N4 N5 C20 C21 -177.7(3)
N4 N5 C20 C25 1.0(5)
C25 C20 C21 C22 1.1(6)
N5 C20 C21 C22 179.9(4)
C20 C21 C22 C23 -1.0(7)
C21 C22 C23 C24 0.9(7)
C22 C23 C24 C25 -1.0(7)
C23 C24 C25 C20 1.2(7)
C21 C20 C25 C24 -1.3(6)
N5 C20 C25 C24 -179.9(4)
O1 C1 C2 C7 1.1(5)
O2 C1 C2 C7 178.5(4)
O1 C1 C2 C3 -179.9(4)
O2 C1 C2 C3 -2.5(5)
C7 C2 C3 O3 179.7(4)
C1 C2 C3 O3 0.6(6)
C7 C2 C3 C4 0.9(6)
C1 C2 C3 C4 -178.2(4)
O3 C3 C4 C5 -179.3(5)
C2 C3 C4 C5 -0.6(7)
C3 C4 C5 C6 -0.4(8)
C4 C5 C6 C7 1.0(8)
C5 C6 C7 C2 -0.6(7)
C3 C2 C7 C6 -0.4(6)
C1 C2 C7 C6 178.7(4)
