#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/20/2212000.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2212000
loop_
_publ_author_name
'Maria Gdaniec'
'Tadeusz Połoński'
_publ_section_title
;
 Phenazine--2,6-dihydroxybenzoic acid (1/1)
;
_journal_coeditor_code           AT2202
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o707
_journal_page_last               o709
_journal_paper_doi               10.1107/S1600536807001195
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C12 H8 N2 , C7 H6 O4'
_chemical_formula_moiety         'C12 H8 N2 , C7 H6 O4'
_chemical_formula_sum            'C19 H14 N2 O4'
_chemical_formula_weight         334.32
_chemical_name_systematic
;
Phenazine--2,6-dihydroxybenzoic acid (1/1)
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.57(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.5921(18)
_cell_length_b                   7.4480(7)
_cell_length_c                   25.297(2)
_cell_measurement_reflns_used    1855
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      4
_cell_volume                     3038.9(6)
_computing_cell_refinement       'CrysAlis CCD'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2004)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2004)'
_computing_molecular_graphics
;
Stereochemical Workstation Operation Manual (Siemens, 1989) and
MERCURY (Version 1.4; Macrae et al.,  2006)
;
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Kuma KM4 κ-geometry CCD area-detector'
_diffrn_measurement_method       ω
_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  0.0378
_diffrn_reflns_av_sigmaI/netI    0.0483
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            7257
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         3.58
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.214
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         2667
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0484
_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)+(0.0534P)²+1.0575P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1040
_refine_ls_wR_factor_ref         0.1125
_reflns_number_gt                1876
_reflns_number_total             2667
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2202.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2212000
_cod_database_fobs_code          2212000
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
C C1 0.54456(13) 0.5591(3) 0.69372(8) 0.0186(5) Uani d . 1
C C2 0.60228(13) 0.6779(3) 0.72671(9) 0.0193(5) Uani d . 1
C C3 0.67036(13) 0.6123(3) 0.76457(9) 0.0221(5) Uani d . 1
H H3 0.7087 0.6928 0.7863 0.026 Uiso calc R 1
C C4 0.68188(14) 0.4285(3) 0.77042(9) 0.0225(5) Uani d . 1
H H4 0.7290 0.3840 0.7960 0.027 Uiso calc R 1
C C5 0.62633(14) 0.3081(3) 0.73978(9) 0.0232(5) Uani d . 1
H H5 0.6352 0.1825 0.7446 0.028 Uiso calc R 1
C C6 0.55765(13) 0.3722(3) 0.70204(9) 0.0199(5) Uani d . 1
C C7 0.47677(14) 0.6363(3) 0.65202(9) 0.0217(5) Uani d . 1
O O1 0.59442(10) 0.8587(2) 0.72250(7) 0.0275(4) Uani d . 1
H H1O 0.5469(18) 0.875(4) 0.6966(12) 0.052(9) Uiso d . 1
O O2 0.50553(10) 0.2462(2) 0.67427(7) 0.0259(4) Uani d . 1
H H2O 0.4614(18) 0.298(4) 0.6525(11) 0.048(9) Uiso d . 1
O O3 0.46821(10) 0.7980(2) 0.64386(7) 0.0335(5) Uani d . 1
O O4 0.42443(9) 0.5186(2) 0.62198(6) 0.0253(4) Uani d . 1
H H4O 0.375(2) 0.588(5) 0.5935(13) 0.076(10) Uiso d . 1
N N1A 0.66289(11) 0.7762(2) 0.49310(7) 0.0204(4) Uani d . 1
C C2A 0.70315(13) 0.8265(3) 0.45475(8) 0.0177(5) Uani d . 1
C C3A 0.65756(14) 0.9112(3) 0.40653(9) 0.0217(5) Uani d . 1
H H3A 0.5999 0.9322 0.4020 0.026 Uiso calc R 1
C C4A 0.69551(14) 0.9622(3) 0.36710(9) 0.0228(5) Uani d . 1
H H4A 0.6641 1.0170 0.3349 0.027 Uiso calc R 1
C C5A 0.71773(14) 0.5656(3) 0.62654(9) 0.0241(5) Uani d . 1
H H5A 0.6919 0.5294 0.6546 0.029 Uiso calc R 1
C C6A 0.67170(14) 0.6434(3) 0.58069(9) 0.0237(5) Uani d . 1
H H6A 0.6138 0.6600 0.5768 0.028 Uiso calc R 1
C C7A 0.70954(13) 0.7004(3) 0.53836(9) 0.0188(5) Uani d . 1
N N1B 0.30893(11) 0.6689(2) 0.54264(7) 0.0195(4) Uani d . 1
C C2B 0.33163(13) 0.7384(3) 0.49899(8) 0.0189(5) Uani d . 1
C C3B 0.41567(14) 0.7319(3) 0.49590(9) 0.0267(6) Uani d . 1
H H3B 0.4560 0.6776 0.5243 0.032 Uiso calc R 1
C C4B 0.43866(15) 0.8033(3) 0.45220(10) 0.0311(6) Uani d . 1
H H4B 0.4953 0.8001 0.4506 0.037 Uiso calc R 1
C C5B 0.12074(15) 0.6174(3) 0.59110(10) 0.0281(6) Uani d . 1
H H5B 0.1034 0.5698 0.6215 0.034 Uiso calc R 1
C C6B 0.20203(14) 0.6086(3) 0.58971(9) 0.0235(5) Uani d . 1
H H6B 0.2412 0.5549 0.6189 0.028 Uiso calc R 1
C C7B 0.22833(13) 0.6801(3) 0.54440(8) 0.0181(5) Uani d . 1
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C6 C1 C2 . . 117.73(19)
C6 C1 C7 . . 123.8(2)
C2 C1 C7 . . 118.4(2)
O1 C2 C3 . . 116.9(2)
O1 C2 C1 . . 122.21(19)
C3 C2 C1 . . 120.9(2)
C4 C3 C2 . . 119.4(2)
C4 C3 H3 . . 120.3
C2 C3 H3 . . 120.3
C5 C4 C3 . . 121.5(2)
C5 C4 H4 . . 119.2
C3 C4 H4 . . 119.2
C4 C5 C6 . . 119.5(2)
C4 C5 H5 . . 120.2
C6 C5 H5 . . 120.2
O2 C6 C5 . . 116.0(2)
O2 C6 C1 . . 123.12(19)
C5 C6 C1 . . 120.8(2)
O3 C7 O4 . . 121.0(2)
O3 C7 C1 . . 123.1(2)
O4 C7 C1 . . 116.0(2)
C2 O1 H1O . . 104(2)
C6 O2 H2O . . 110.6(18)
C7 O4 H4O . . 110.7(18)
C7A N1A C2A . . 116.34(19)
N1A C2A C3A . . 119.0(2)
N1A C2A C7A . 7_666 121.98(19)
C3A C2A C7A . 7_666 119.0(2)
C4A C3A C2A . . 120.7(2)
C4A C3A H3A . . 119.6
C2A C3A H3A . . 119.6
C3A C4A C5A . 7_666 120.6(2)
C3A C4A H4A . . 119.7
C5A C4A H4A 7_666 . 119.7
C6A C5A C4A . 7_666 120.6(2)
C6A C5A H5A . . 119.7
C4A C5A H5A 7_666 . 119.7
C5A C6A C7A . . 120.6(2)
C5A C6A H6A . . 119.7
C7A C6A H6A . . 119.7
N1A C7A C6A . . 119.8(2)
N1A C7A C2A . 7_666 121.7(2)
C6A C7A C2A . 7_666 118.5(2)
C2B N1B C7B . . 118.13(18)
N1B C2B C3B . . 120.0(2)
N1B C2B C7B . 7_566 120.81(19)
C3B C2B C7B . 7_566 119.2(2)
C4B C3B C2B . . 120.0(2)
C4B C3B H3B . . 120.0
C2B C3B H3B . . 120.0
C3B C4B C5B . 7_566 120.9(2)
C3B C4B H4B . . 119.5
C5B C4B H4B 7_566 . 119.5
C6B C5B C4B . 7_566 120.9(2)
C6B C5B H5B . . 119.5
C4B C5B H5B 7_566 . 119.5
C5B C6B C7B . . 119.8(2)
C5B C6B H6B . . 120.1
C7B C6B H6B . . 120.1
N1B C7B C6B . . 119.78(19)
N1B C7B C2B . 7_566 121.06(19)
C6B C7B C2B . 7_566 119.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C6 . 1.417(3)
C1 C2 . 1.422(3)
C1 C7 . 1.467(3)
C2 O1 . 1.355(3)
C2 C3 . 1.387(3)
C3 C4 . 1.386(3)
C3 H3 . 0.9500
C4 C5 . 1.385(3)
C4 H4 . 0.9500
C5 C6 . 1.389(3)
C5 H5 . 0.9500
C6 O2 . 1.355(3)
C7 O3 . 1.225(3)
C7 O4 . 1.338(3)
O1 H1O . 0.91(3)
O2 H2O . 0.89(3)
O4 H4O . 1.09(3)
N1A C7A . 1.347(3)
N1A C2A . 1.353(3)
C2A C3A . 1.423(3)
C2A C7A 7_666 1.432(3)
C3A C4A . 1.353(3)
C3A H3A . 0.9500
C4A C5A 7_666 1.425(3)
C4A H4A . 0.9500
C5A C6A . 1.360(3)
C5A H5A . 0.9500
C6A C7A . 1.427(3)
C6A H6A . 0.9500
N1B C2B . 1.351(3)
N1B C7B . 1.351(3)
C2B C3B . 1.416(3)
C2B C7B 7_566 1.432(3)
C3B C4B . 1.360(3)
C3B H3B . 0.9500
C4B C5B 7_566 1.419(3)
C4B H4B . 0.9500
C5B C6B . 1.359(3)
C5B H5B . 0.9500
C6B C7B . 1.422(3)
C6B H6B . 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O2 H2O O4 . 0.89(3) 1.86(3) 2.616(2) 141(3)
O1 H1O O3 . 0.91(3) 1.73(3) 2.568(2) 152(3)
O4 H4O N1B . 1.09(3) 1.60(3) 2.674(2) 168(3)
C4B H4B N1A . 0.95 2.74 3.626(3) 155
C3A H3A O3 5_676 0.95 2.46 3.070(3) 122
C3A H3A O2 5_666 0.95 2.64 3.206(3) 119
C5 H5 O1 1_545 0.95 2.53 3.401(3) 152
C5B H5B O2 3_455 0.95 2.68 3.300(3) 124
