#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/84/2218460.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_2218460
loop_
_publ_author_name
'Li, Xiao-Feng'
'An, Yan'
'Yin, Yan-Sheng'
_publ_section_title
;
 2,3-Diaminophenazine tetrahydrate
;
_journal_coeditor_code           LH2601
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1000
_journal_paper_doi               10.1107/S1600536808009598
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C12 H10 N4, 4H2 O'
_chemical_formula_moiety         'C12 H10 N4, 4(H2 O)'
_chemical_formula_sum            'C12 H18 N4 O4'
_chemical_formula_weight         282.30
_chemical_name_systematic
;
2,3-Diaminophenazine tetrahydrate
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.7593(18)
_cell_length_b                   18.1200(19)
_cell_length_c                   4.7834(5)
_cell_measurement_reflns_used    3569
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.32
_cell_measurement_theta_min      2.65
_cell_volume                     1452.6(3)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX area-detector'
_diffrn_measurement_method       'φ and 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  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0217
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            7735
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.12
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.9772
_exptl_absorpt_correction_T_min  0.9646
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Black
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.123
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         1608
_refine_ls_number_restraints     17
_refine_ls_restrained_S_all      1.135
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0478
_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)+(0.0963P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1397
_reflns_number_gt                1432
_reflns_number_total             1608
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2601.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2218460
_cod_database_fobs_code          2218460
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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
N N1 0.51508(13) 0.31719(12) 0.3965(5) 0.0417(6) Uani d . 1
N N2 0.51933(12) 0.16406(12) 0.2821(6) 0.0410(5) Uani d . 1
C C10 0.46946(14) 0.20894(15) 0.1460(6) 0.0393(6) Uani d . 1
C C11 0.41763(15) 0.18021(16) -0.0623(7) 0.0443(7) Uani d . 1
H H11A 0.4184 0.1299 -0.1008 0.053 Uiso calc R 1
C C1 0.56542(15) 0.27142(16) 0.5338(6) 0.0418(7) Uani d . 1
C C12 0.36660(15) 0.22488(17) -0.2076(6) 0.0445(7) Uani d . 1
C C8 0.41408(16) 0.33188(16) 0.0507(7) 0.0456(7) Uani d . 1
H H8A 0.4123 0.3823 0.0873 0.055 Uiso calc R 1
C C9 0.46739(15) 0.28738(15) 0.2042(6) 0.0394(6) Uani d . 1
N N4 0.31334(15) 0.19700(17) -0.3960(7) 0.0603(8) Uani d D 1
H H4B 0.3134(18) 0.1476(6) -0.403(10) 0.072 Uiso d D 1
H H4C 0.2916(19) 0.2287(16) -0.520(7) 0.072 Uiso d D 1
N N3 0.30987(17) 0.34664(19) -0.2858(6) 0.0630(8) Uani d D 1
H H3B 0.315(2) 0.3961(7) -0.263(12) 0.076 Uiso d D 1
H H3C 0.2912(19) 0.333(2) -0.454(4) 0.076 Uiso d D 1
C C5 0.62032(15) 0.14891(17) 0.6301(7) 0.0498(7) Uani d . 1
H H5A 0.6222 0.0985 0.5942 0.060 Uiso calc R 1
C C6 0.56701(14) 0.19474(15) 0.4760(6) 0.0401(6) Uani d . 1
C C2 0.61674(16) 0.30014(19) 0.7428(7) 0.0512(8) Uani d . 1
H H2A 0.6163 0.3504 0.7828 0.061 Uiso calc R 1
C C7 0.36499(15) 0.30342(16) -0.1501(6) 0.0446(7) Uani d . 1
C C4 0.66820(16) 0.1785(2) 0.8286(7) 0.0561(8) Uani d . 1
H H4A 0.7025 0.1480 0.9289 0.067 Uiso calc R 1
C C3 0.66680(18) 0.25428(18) 0.8851(7) 0.0576(9) Uani d . 1
H H3A 0.7004 0.2736 1.0213 0.069 Uiso calc R 1
O O4W 0.54392(14) 0.01642(12) 0.1437(6) 0.0592(6) Uani d D 1
O O3W 0.53446(19) 0.47020(15) 0.4439(8) 0.0798(8) Uani d D 1
O O2W 0.29410(18) 0.02670(19) 0.5763(7) 0.0818(8) Uani d D 1
O O1W 0.7032(3) 0.4897(3) 0.3542(10) 0.1042(11) Uani d D 1
H H4WB 0.541(2) 0.0631(11) 0.182(8) 0.088(14) Uiso d D 1
H H3WB 0.535(3) 0.4238(14) 0.396(16) 0.16(3) Uiso d D 1
H H4WA 0.516(2) 0.0085(18) -0.004(7) 0.070(12) Uiso d D 1
H H3WA 0.4832(14) 0.481(2) 0.455(16) 0.14(2) Uiso d D 1
H H2WA 0.3416(11) 0.014(2) 0.601(11) 0.102(16) Uiso d D 1
H H1WA 0.723(3) 0.469(4) 0.495(12) 0.22(4) Uiso d D 1
H H2WB 0.266(2) 0.016(2) 0.724(8) 0.093(16) Uiso d D 1
H H1WB 0.6547(14) 0.478(2) 0.330(13) 0.11(2) Uiso d 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
C9 N1 C1 117.4(2)
C10 N2 C6 117.2(2)
N2 C10 C11 120.1(2)
N2 C10 C9 121.2(2)
C11 C10 C9 118.7(2)
C12 C11 C10 121.5(3)
C12 C11 H11A 119.3
C10 C11 H11A 119.3
N1 C1 C6 121.2(2)
N1 C1 C2 119.7(3)
C6 C1 C2 119.1(3)
N4 C12 C11 121.7(3)
N4 C12 C7 118.4(3)
C11 C12 C7 119.8(3)
C7 C8 C9 122.2(3)
C7 C8 H8A 118.9
C9 C8 H8A 118.9
N1 C9 C8 120.5(3)
N1 C9 C10 121.1(2)
C8 C9 C10 118.4(2)
C12 N4 H4B 113(3)
C12 N4 H4C 118(2)
H4B N4 H4C 128(4)
C7 N3 H3B 117(3)
C7 N3 H3C 120(3)
H3B N3 H3C 114(4)
C4 C5 C6 120.3(3)
C4 C5 H5A 119.9
C6 C5 H5A 119.9
N2 C6 C1 121.9(2)
N2 C6 C5 119.2(3)
C1 C6 C5 118.8(2)
C3 C2 C1 120.1(3)
C3 C2 H2A 119.9
C1 C2 H2A 119.9
C8 C7 N3 121.5(3)
C8 C7 C12 119.5(3)
N3 C7 C12 118.9(3)
C5 C4 C3 120.9(3)
C5 C4 H4A 119.6
C3 C4 H4A 119.6
C2 C3 C4 120.8(3)
C2 C3 H3A 119.6
C4 C3 H3A 119.6
H4WB O4W H4WA 108(2)
H3WB O3W H3WA 105(2)
H2WA O2W H2WB 109(2)
H1WA O1W H1WB 112(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C9 1.333(3)
N1 C1 1.353(3)
N2 C10 1.335(3)
N2 C6 1.345(4)
C10 C11 1.421(4)
C10 C9 1.449(4)
C11 C12 1.367(4)
C11 H11A 0.9300
C1 C6 1.417(4)
C1 C2 1.417(4)
C12 N4 1.366(4)
C12 C7 1.450(4)
C8 C7 1.366(4)
C8 C9 1.410(4)
C8 H8A 0.9300
N4 H4B 0.895(10)
N4 H4C 0.90(3)
N3 C7 1.374(4)
N3 H3B 0.906(10)
N3 H3C 0.895(11)
C5 C4 1.353(5)
C5 C6 1.425(4)
C5 H5A 0.9300
C2 C3 1.363(4)
C2 H2A 0.9300
C4 C3 1.400(4)
C4 H4A 0.9300
C3 H3A 0.9300
O4W H4WB 0.867(17)
O4W H4WA 0.855(19)
O3W H3WB 0.872(19)
O3W H3WA 0.883(19)
O2W H2WA 0.837(19)
O2W H2WB 0.87(4)
O1W H1WA 0.84(6)
O1W H1WB 0.849(18)
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
N4 H4B O2W 1_554 0.895(10) 2.218(12) 3.105(5) 171(3)
N4 H4C N4 4_554 0.90(3) 2.58(3) 3.198(3) 126(3)
N3 H3B O1W 2_664 0.906(10) 2.165(16) 3.048(6) 165(4)
N3 H3C N3 4_554 0.895(11) 2.33(2) 3.122(4) 147(3)
O4W H4WA O4W 2_654 0.855(19) 2.017(19) 2.871(3) 176(4)
O4W H4WB N2 . 0.867(17) 1.924(19) 2.787(3) 173(4)
O3W H3WB N1 . 0.872(19) 1.96(3) 2.801(3) 161(6)
O2W H2WA O4W 2_655 0.84(2) 2.01(2) 2.843(4) 178(5)
O1W H1WA O1W 4_655 0.84(6) 2.15(6) 2.860(7) 142(6)
O2W H2WB O2W 4_555 0.87(4) 1.97(4) 2.812(5) 161(3)
O1W H1WB O3W . 0.85(3) 2.09(3) 2.882(6) 155(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
C6 N2 C10 C11 179.8(2)
C6 N2 C10 C9 0.4(4)
N2 C10 C11 C12 -179.2(2)
C9 C10 C11 C12 0.2(4)
C9 N1 C1 C6 -0.3(4)
C9 N1 C1 C2 -179.2(2)
C10 C11 C12 N4 -176.0(3)
C10 C11 C12 C7 0.2(4)
C1 N1 C9 C8 -179.3(2)
C1 N1 C9 C10 0.2(4)
C7 C8 C9 N1 179.2(2)
C7 C8 C9 C10 -0.2(4)
N2 C10 C9 N1 -0.3(3)
C11 C10 C9 N1 -179.6(3)
N2 C10 C9 C8 179.2(3)
C11 C10 C9 C8 -0.2(3)
C10 N2 C6 C1 -0.5(4)
C10 N2 C6 C5 179.0(2)
N1 C1 C6 N2 0.5(4)
C2 C1 C6 N2 179.4(3)
N1 C1 C6 C5 -179.0(3)
C2 C1 C6 C5 0.0(4)
C4 C5 C6 N2 -179.2(3)
C4 C5 C6 C1 0.2(4)
N1 C1 C2 C3 179.0(3)
C6 C1 C2 C3 0.0(4)
C9 C8 C7 N3 175.9(3)
C9 C8 C7 C12 0.6(4)
N4 C12 C7 C8 175.8(3)
C11 C12 C7 C8 -0.6(4)
N4 C12 C7 N3 0.4(4)
C11 C12 C7 N3 -176.0(3)
C6 C5 C4 C3 -0.5(4)
C1 C2 C3 C4 -0.3(5)
C5 C4 C3 C2 0.5(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655504
