#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/77/2237700.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_2237700
loop_
_publ_author_name
'deGeorge, Joseph'
'Landee, Christopher P.'
'Turnbull, Mark M.'
_publ_section_title
;
 Phenazin-5-ium hydrogen sulfate monohydrate
;
_journal_coeditor_code           SJ5299
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o471
_journal_paper_doi               10.1107/S160053681300562X
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C12 H9 N2 +, H S O4 -, H2 O'
_chemical_formula_moiety         'C12 H9 N2 +, H O4 S -, H2 O'
_chemical_formula_sum            'C12 H12 N2 O5 S'
_chemical_formula_weight         296.30
_chemical_name_systematic
;
Phenazin-5-ium hydrogen sulfate monohydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_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                89.693(4)
_cell_angle_beta                 87.202(5)
_cell_angle_gamma                76.412(5)
_cell_formula_units_Z            2
_cell_length_a                   5.6565(4)
_cell_length_b                   10.4019(6)
_cell_length_c                   10.9500(5)
_cell_measurement_reflns_used    3015
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.6591
_cell_measurement_theta_min      4.0387
_cell_volume                     625.49(7)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008), enCIFer (Allen et al., 2004)
and
publCIF (Westrip, 2010)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 10.6501
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Agilent SuperNova (Dual, Cu at zero, Atlas)'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0131
_diffrn_reflns_av_sigmaI/netI    0.0166
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3789
_diffrn_reflns_theta_full        70.06
_diffrn_reflns_theta_max         70.06
_diffrn_reflns_theta_min         4.04
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.533
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2011)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.385
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2341
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0320
_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)+(0.0466P)²+0.3904P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0881
_reflns_number_gt                2276
_reflns_number_total             2341
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj5299.cif
_cod_data_source_block           I
_cod_original_cell_volume        625.49(6)
_cod_database_code               2237700
_cod_database_fobs_code          2237700
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_symmetry_multiplicity
N N1 -0.2593(2) 0.82964(13) 0.67912(12) 0.0146(3) Uani d . 1 1
H H1 -0.121(4) 0.782(2) 0.6983(18) 0.018 Uiso d . 1 1
C C2 -0.3721(3) 0.78622(15) 0.58835(14) 0.0147(3) Uani d . 1 1
C C3 -0.2635(3) 0.66885(16) 0.52306(15) 0.0196(3) Uani d . 1 1
H H3 -0.1104 0.6194 0.5420 0.024 Uiso calc R 1 1
C C4 -0.3861(3) 0.62898(17) 0.43183(15) 0.0223(4) Uani d . 1 1
H H4 -0.3161 0.5514 0.3890 0.027 Uiso calc R 1 1
C C5 -0.6203(3) 0.70454(17) 0.40110(15) 0.0217(4) Uani d . 1 1
H H5 -0.6999 0.6760 0.3379 0.026 Uiso calc R 1 1
C C6 -0.7286(3) 0.81763(17) 0.46292(15) 0.0192(3) Uani d . 1 1
H H6 -0.8810 0.8660 0.4416 0.023 Uiso calc R 1 1
C C7 -0.6090(3) 0.86222(15) 0.56042(14) 0.0152(3) Uani d . 1 1
N N8 -0.7194(2) 0.97138(13) 0.62387(12) 0.0170(3) Uani d . 1 1
C C9 -0.6022(3) 1.00957(15) 0.71603(14) 0.0156(3) Uani d . 1 1
C C10 -0.7157(3) 1.12367(16) 0.78748(15) 0.0195(3) Uani d . 1 1
H H10 -0.8713 1.1714 0.7708 0.023 Uiso calc R 1 1
C C11 -0.5958(3) 1.16250(16) 0.88007(15) 0.0211(4) Uani d . 1 1
H H11 -0.6713 1.2364 0.9269 0.025 Uiso calc R 1 1
C C12 -0.3575(3) 1.09182(16) 0.90608(15) 0.0209(4) Uani d . 1 1
H H12 -0.2782 1.1214 0.9688 0.025 Uiso calc R 1 1
C C13 -0.2415(3) 0.98128(16) 0.84123(15) 0.0186(3) Uani d . 1 1
H H13 -0.0857 0.9352 0.8597 0.022 Uiso calc R 1 1
C C14 -0.3633(3) 0.93855(15) 0.74565(14) 0.0142(3) Uani d . 1 1
S S1 0.28595(6) 0.63836(3) 0.83817(3) 0.01403(14) Uani d . 1 1
O O1 0.1783(2) 0.67614(11) 0.72006(10) 0.0209(3) Uani d . 1 1
O O2 0.3077(2) 0.48835(11) 0.85361(11) 0.0193(3) Uani d . 1 1
H H2 0.155(4) 0.469(2) 0.8530(18) 0.023 Uiso d . 1 1
O O3 0.1275(2) 0.70674(11) 0.93855(11) 0.0214(3) Uani d . 1 1
O O4 0.5331(2) 0.65395(12) 0.84063(12) 0.0247(3) Uani d . 1 1
O O1S -0.0979(2) 0.42771(13) 0.84748(11) 0.0207(3) Uani d . 1 1
H H1A -0.221(4) 0.498(2) 0.8448(19) 0.025 Uiso d . 1 1
H H1B -0.120(4) 0.387(2) 0.912(2) 0.025 Uiso d . 1 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
S S 0.3331 0.5567 '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
C2 N1 C14 122.42(14)
C2 N1 H1 117.8(13)
C14 N1 H1 119.6(13)
N1 C2 C3 121.43(14)
N1 C2 C7 117.80(14)
C3 C2 C7 120.77(14)
C4 C3 C2 119.09(15)
C4 C3 H3 120.5
C2 C3 H3 120.5
C3 C4 C5 121.01(15)
C3 C4 H4 119.5
C5 C4 H4 119.5
C6 C5 C4 120.90(15)
C6 C5 H5 119.5
C4 C5 H5 119.5
C5 C6 C7 120.12(15)
C5 C6 H6 119.9
C7 C6 H6 119.9
N8 C7 C6 120.05(14)
N8 C7 C2 121.85(14)
C6 C7 C2 118.09(14)
C7 N8 C9 118.37(14)
N8 C9 C10 120.09(14)
N8 C9 C14 121.81(14)
C10 C9 C14 118.10(14)
C11 C10 C9 119.91(15)
C11 C10 H10 120.0
C9 C10 H10 120.0
C10 C11 C12 120.87(15)
C10 C11 H11 119.6
C12 C11 H11 119.6
C13 C12 C11 121.57(15)
C13 C12 H12 119.2
C11 C12 H12 119.2
C12 C13 C14 118.48(15)
C12 C13 H13 120.8
C14 C13 H13 120.8
N1 C14 C13 121.24(14)
N1 C14 C9 117.71(14)
C13 C14 C9 121.05(14)
O4 S1 O3 113.27(7)
O4 S1 O1 112.32(7)
O3 S1 O1 110.75(7)
O4 S1 O2 104.85(7)
O3 S1 O2 107.93(7)
O1 S1 O2 107.28(7)
S1 O2 H2 111.1(13)
H1A O1S H1B 107(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.342(2)
N1 C14 1.347(2)
N1 H1 0.86(2)
C2 C3 1.412(2)
C2 C7 1.433(2)
C3 C4 1.363(2)
C3 H3 0.9300
C4 C5 1.428(2)
C4 H4 0.9300
C5 C6 1.359(2)
C5 H5 0.9300
C6 C7 1.427(2)
C6 H6 0.9300
C7 N8 1.340(2)
N8 C9 1.345(2)
C9 C10 1.427(2)
C9 C14 1.431(2)
C10 C11 1.360(2)
C10 H10 0.9300
C11 C12 1.417(2)
C11 H11 0.9300
C12 C13 1.366(2)
C12 H12 0.9300
C13 C14 1.410(2)
C13 H13 0.9300
S1 O4 1.4465(12)
S1 O3 1.4595(12)
S1 O1 1.4685(12)
S1 O2 1.5452(11)
O2 H2 0.93(2)
O1S H1A 0.89(2)
O1S H1B 0.84(2)
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
N1 H1 O1 . 0.86(2) 1.81(2) 2.6685(18) 173.3(19)
O2 H2 O1S . 0.93(2) 1.59(2) 2.5223(16) 177(2)
O1S H1A O4 1_455 0.89(2) 1.87(2) 2.7577(18) 176(2)
O1S H1B O3 2_567 0.84(2) 1.90(2) 2.7405(18) 173(2)
C6 H6 N8 2_376 0.93 2.61 3.538(2) 172.2
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C14 N1 C2 C3 -177.42(14)
C14 N1 C2 C7 1.9(2)
N1 C2 C3 C4 179.87(15)
C7 C2 C3 C4 0.6(2)
C2 C3 C4 C5 0.5(3)
C3 C4 C5 C6 -0.7(3)
C4 C5 C6 C7 -0.3(3)
C5 C6 C7 N8 -177.83(15)
C5 C6 C7 C2 1.4(2)
N1 C2 C7 N8 -1.6(2)
C3 C2 C7 N8 177.64(15)
N1 C2 C7 C6 179.15(13)
C3 C2 C7 C6 -1.6(2)
C6 C7 N8 C9 179.27(14)
C2 C7 N8 C9 0.1(2)
C7 N8 C9 C10 -178.66(14)
C7 N8 C9 C14 1.3(2)
N8 C9 C10 C11 -179.55(15)
C14 C9 C10 C11 0.5(2)
C9 C10 C11 C12 0.7(2)
C10 C11 C12 C13 -1.3(3)
C11 C12 C13 C14 0.6(2)
C2 N1 C14 C13 179.42(14)
C2 N1 C14 C9 -0.6(2)
C12 C13 C14 N1 -179.43(15)
C12 C13 C14 C9 0.6(2)
N8 C9 C14 N1 -1.1(2)
C10 C9 C14 N1 178.86(14)
N8 C9 C14 C13 178.92(14)
C10 C9 C14 C13 -1.1(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658398
