#------------------------------------------------------------------------------
#$Date: 2025-08-22 14:50:14 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301863 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/49/7204918.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_7204918
loop_
_publ_author_name
'Batchelor, Elaine'
'Klinowski, Jacek'
'Jones, William'
_publ_section_title
;
 Crystal engineering using co‐crystallisation of phenazine with
 dicarboxylic acids
;
_journal_issue                   4
_journal_name_full               'Journal of Materials Chemistry'
_journal_page_first              839
_journal_paper_doi               10.1039/a908214j
_journal_volume                  10
_journal_year                    2000
_chemical_compound_source        Aldrich
_chemical_formula_moiety         'C12 H8 N2, C5 H6 O4'
_chemical_formula_sum            'C17 H14 N2 O4'
_chemical_formula_weight         310.30
_chemical_name_common            'Phenazine mesaconic acid'
_chemical_name_systematic
; 
 dibenzopyrazine trans-2-methyl-2-butenedioic acid 
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 127.46(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   26.833(26)
_cell_length_b                   7.095(4)
_cell_length_c                   19.613(27)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      15
_cell_volume                     2964(6)
_computing_cell_refinement       'CAD4, SETANG <Enraf Nonius>'
_computing_data_collection       'CAD4 <Enraf Nonius>'
_computing_data_reduction
'TEXSAN <Molecular Structure Corporation, 1995>'
_computing_molecular_graphics
'TEXSAN <Molecular Structure Corporation, 1995>'
_computing_publication_material
'SHELXL-93 (Sheldrick, 1993), SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement
'SHELXL-93 (Sheldrick, 1993), SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measurement_device       'Enraf Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0375
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2689
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         1.91
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  3600
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange-yellow
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured '
_exptl_crystal_description       'rectangular plate '
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0059(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.014
_refine_ls_goodness_of_fit_obs   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2601
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_restrained_S_obs      1.085
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_obs          0.0407
_refine_ls_shift/esd_max         0.011
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0606P)²+1.0880P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1183
_refine_ls_wR_factor_obs         0.1010
_reflns_number_observed          1733
_reflns_number_total             2601
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            a908214j.txt
_cod_data_source_block           2d
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0606P)^2^+1.0880P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0606P)^2^+1.0880P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        2963.9(53)
_cod_database_code               7204918
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_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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
O3 O 0.46646(7) 0.7227(2) 0.04498(9) 0.0493(4) Uani 1 d . .
H3O H 0.4274(13) 0.6864(42) 0.0230(17) 0.084(9) Uiso 1 d . .
O1 O 0.63187(8) 0.8758(3) -0.04958(11) 0.0593(5) Uani 1 d . .
H1O H 0.6737(15) 0.9134(44) -0.0206(18) 0.100(10) Uiso 1 d . .
O2 O 0.65233(7) 0.9206(3) 0.07641(10) 0.0786(7) Uani 1 d . .
O4 O 0.42986(7) 0.6705(3) -0.08961(11) 0.0724(6) Uani 1 d . .
N1 N 0.64893(7) 0.3835(3) -0.00896(10) 0.0383(4) Uani 1 d . .
N2 N 0.75412(8) 0.5105(2) 0.00410(11) 0.0359(4) Uani 1 d . .
C16 C 0.47176(9) 0.7201(3) -0.01811(13) 0.0397(5) Uani 1 d . .
C15 C 0.53428(9) 0.7829(3) 0.01041(13) 0.0403(5) Uani 1 d . .
H15 H 0.56479(9) 0.8035(3) 0.06888(13) 0.044(6) Uiso 1 calc R .
C14 C 0.55039(9) 0.8122(3) -0.04060(12) 0.0379(5) Uani 1 d . .
C17 C 0.50881(11) 0.7927(5) -0.13614(14) 0.0677(8) Uani 1 d . .
H17A H 0.5256(7) 0.6983(27) -0.1521(2) 0.153(9) Uiso 1 calc R .
H17B H 0.5067(10) 0.9111(11) -0.1615(2) 0.153(9) Uiso 1 calc R .
H17C H 0.4675(4) 0.7563(38) -0.1562(2) 0.153(9) Uiso 1 calc R .
C13 C 0.61712(9) 0.8750(3) 0.00318(13) 0.0408(5) Uani 1 d . .
C11 C 0.70704(10) 0.4222(4) 0.14256(13) 0.0487(6) Uani 1 d . .
H11 H 0.67325(10) 0.3772(4) 0.13969(13) 0.060(2) Uiso 1 calc R .
C10 C 0.76027(11) 0.4752(4) 0.21901(14) 0.0556(7) Uani 1 d . .
H10 H 0.76276(11) 0.4655(4) 0.26829(14) 0.060(2) Uiso 1 calc R .
C9 C 0.81216(10) 0.5452(4) 0.22527(14) 0.0505(6) Uani 1 d . .
H9 H 0.84808(10) 0.5830(4) 0.27838(14) 0.060(2) Uiso 1 calc R .
C8 C 0.81022(9) 0.5577(3) 0.15519(13) 0.0431(5) Uani 1 d . .
H8 H 0.84483(9) 0.6033(3) 0.16024(13) 0.060(2) Uiso 1 calc R .
C7 C 0.75559(9) 0.5016(3) 0.07368(12) 0.0333(5) Uani 1 d . .
C6 C 0.70088(8) 0.4583(3) -0.07194(12) 0.0331(5) Uani 1 d . .
C5 C 0.69726(10) 0.4665(3) -0.14681(13) 0.0435(5) Uani 1 d . .
H5 H 0.73188(10) 0.5065(3) -0.14302(13) 0.060(2) Uiso 1 calc R .
C4 C 0.64420(11) 0.4171(4) -0.22349(14) 0.0526(6) Uani 1 d . .
H4 H 0.64223(11) 0.4247(4) -0.27242(14) 0.060(2) Uiso 1 calc R .
C3 C 0.59136(10) 0.3535(4) -0.23034(14) 0.0530(7) Uani 1 d . .
H3 H 0.55503(10) 0.3192(4) -0.28375(14) 0.060(2) Uiso 1 calc R .
C2 C 0.59301(9) 0.3421(4) -0.16027(13) 0.0485(6) Uani 1 d . .
H2 H 0.55788(9) 0.2996(4) -0.16593(13) 0.060(2) Uiso 1 calc R .
C1 C 0.64751(9) 0.3941(3) -0.07850(12) 0.0352(5) Uani 1 d . .
C12 C 0.70236(9) 0.4346(3) 0.06703(12) 0.0352(5) Uani 1 d . .
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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C12 117.6(2) . . ?
C7 N2 C6 118.0(2) . . ?
O4 C16 O3 122.6(2) . . ?
O4 C16 C15 124.9(2) . . ?
O3 C16 C15 112.5(2) . . ?
C14 C15 C16 125.3(2) . . ?
C15 C14 C17 126.5(2) . . ?
C15 C14 C13 115.9(2) . . ?
C17 C14 C13 117.6(2) . . ?
O2 C13 O1 123.5(2) . . ?
O2 C13 C14 124.4(2) . . ?
O1 C13 C14 112.0(2) . . ?
C10 C11 C12 120.4(2) . . ?
C11 C10 C9 121.1(2) . . ?
C8 C9 C10 120.7(2) . . ?
C9 C8 C7 120.2(2) . . ?
N2 C7 C8 120.2(2) . . ?
N2 C7 C12 120.7(2) . . ?
C8 C7 C12 119.0(2) . . ?
N2 C6 C5 119.8(2) . . ?
N2 C6 C1 121.1(2) . . ?
C5 C6 C1 119.1(2) . . ?
C4 C5 C6 120.6(2) . . ?
C5 C4 C3 120.5(2) . . ?
C2 C3 C4 120.8(2) . . ?
C3 C2 C1 120.7(2) . . ?
N1 C1 C2 120.6(2) . . ?
N1 C1 C6 121.2(2) . . ?
C2 C1 C6 118.2(2) . . ?
N1 C12 C11 120.0(2) . . ?
N1 C12 C7 121.4(2) . . ?
C11 C12 C7 118.5(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C16 1.329(3) . ?
O1 C13 1.314(3) . ?
O2 C13 1.187(3) . ?
O4 C16 1.198(3) . ?
N1 C1 1.343(3) . ?
N1 C12 1.345(3) . ?
N2 C7 1.343(3) . ?
N2 C6 1.346(3) . ?
C16 C15 1.478(3) . ?
C15 C14 1.326(3) . ?
C14 C17 1.494(4) . ?
C14 C13 1.507(3) . ?
C11 C10 1.351(4) . ?
C11 C12 1.411(3) . ?
C10 C9 1.411(3) . ?
C9 C8 1.346(3) . ?
C8 C7 1.419(3) . ?
C7 C12 1.434(3) . ?
C6 C5 1.413(3) . ?
C6 C1 1.432(3) . ?
C5 C4 1.344(4) . ?
C4 C3 1.414(3) . ?
C3 C2 1.350(3) . ?
C2 C1 1.412(3) . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 C16 C15 C14 7.6(4) . . . . ?
O3 C16 C15 C14 -172.8(2) . . . . ?
C16 C15 C14 C17 1.6(4) . . . . ?
C16 C15 C14 C13 -179.7(2) . . . . ?
C15 C14 C13 O2 -9.5(3) . . . . ?
C17 C14 C13 O2 169.3(3) . . . . ?
C15 C14 C13 O1 171.2(2) . . . . ?
C17 C14 C13 O1 -10.0(3) . . . . ?
C12 C11 C10 C9 0.4(4) . . . . ?
C11 C10 C9 C8 -1.1(4) . . . . ?
C10 C9 C8 C7 0.4(4) . . . . ?
C6 N2 C7 C8 -179.1(2) . . . . ?
C6 N2 C7 C12 1.3(3) . . . . ?
C9 C8 C7 N2 -178.6(2) . . . . ?
C9 C8 C7 C12 1.0(3) . . . . ?
C7 N2 C6 C5 179.6(2) . . . . ?
C7 N2 C6 C1 -0.4(3) . . . . ?
N2 C6 C5 C4 -179.2(2) . . . . ?
C1 C6 C5 C4 0.8(3) . . . . ?
C6 C5 C4 C3 -0.9(4) . . . . ?
C5 C4 C3 C2 0.3(4) . . . . ?
C4 C3 C2 C1 0.2(4) . . . . ?
C12 N1 C1 C2 179.8(2) . . . . ?
C12 N1 C1 C6 -0.3(3) . . . . ?
C3 C2 C1 N1 179.7(2) . . . . ?
C3 C2 C1 C6 -0.3(3) . . . . ?
N2 C6 C1 N1 -0.2(3) . . . . ?
C5 C6 C1 N1 179.8(2) . . . . ?
N2 C6 C1 C2 179.8(2) . . . . ?
C5 C6 C1 C2 -0.3(3) . . . . ?
C1 N1 C12 C11 -178.5(2) . . . . ?
C1 N1 C12 C7 1.2(3) . . . . ?
C10 C11 C12 N1 -179.2(2) . . . . ?
C10 C11 C12 C7 1.0(3) . . . . ?
N2 C7 C12 N1 -1.8(3) . . . . ?
C8 C7 C12 N1 178.6(2) . . . . ?
N2 C7 C12 C11 177.9(2) . . . . ?
C8 C7 C12 C11 -1.7(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21190260
2 PubChem 139195556
