#===================================================================
data_global
#====================================================================

_audit_creation_method     'from SHELXL97 CIF, local template and enCIFer'
#===================================================================
# 1. SUBMISSION DETAILS 
_publ_contact_author_name       'Dr Scott McKay'

_publ_contact_author_address
;
Central Missouri State University
Department of Chemistry and Physics
Warrensburg, MO 64093
;

_publ_contact_author_email        'mckay@cmsu1.cmsu.edu'
_publ_contact_author_fax          '660-543-4843'
_publ_contact_author_phone        '660-543-4949'


_publ_requested_journal           'Acta Crystallographica E'
_publ_requested_category          EO
_publ_requested_coeditor_name     ?

_publ_contact_letter
;
Please consider this CIF submission for publication as 
 a communication in CrystEngComm.  

The CIF has passed the Chester CHECKCIF routines (please see
 _publ_section_exptl_refinement) and gives a 
satisfactory PRINTCIF file.


Scott McKay
;

#=====================================================================
# 2. PROCESSING SUMMARY  (IUCr Office Use Only)

_journal_date_recd_electronic  ?
_journal_date_to_coeditor      ?
_journal_date_from_coeditor    ?
_journal_date_accepted         ?
_journal_date_printers_first   ?
_journal_date_printers_final   ?
_journal_date_proofs_out       ?
_journal_date_proofs_in        ?
_journal_coeditor_name         ?
_journal_coeditor_code         ?
_journal_coeditor_notes
; 
;
_journal_techeditor_code       ?
_journal_techeditor_notes
; 
;
_journal_coden_ASTM            ACSCEE
_journal_name_full             ?
_journal_year                  ?
_journal_volume                ?
_journal_issue                 ?
_journal_page_first            ?
_journal_page_last             ?
_journal_suppl_publ_number      ?
_journal_suppl_publ_pages       ?

#=====================================================================
# 3. TITLE AND AUTHOR LIST 

_publ_section_title
;
2,7-Dimethoxy-5,10-bis(p-anisyl)-5,10-dihydrophenazine tricyanomethanide
;

loop_
 _publ_author_name
 _publ_author_address
 _publ_author_footnote
'McKay, Scott E.'
;
Central Missouri State University
Department of Chemistry and Physics
Warrensburg, MO 64093
;
?
'Wheeler, Kraig A.'
;
Eastern Illinois University
Department of Chemistry
600 Lincoln Avenue
Charleston, IL 61920
;
?
'Blackstock, Silas C.' 
;
University of Alabama
Department of Chemistry 
Tuscaloosa, Alabama 35487
;
?

#======================================================================
# 4. TEXT
_publ_section_abstract
;

;

_publ_section_comment
;

;

_publ_section_acknowledgements
;  

;

_publ_section_references
; 

;

_publ_section_figure_captions
; 

;

_publ_section_exptl_prep
;

;

_publ_section_exptl_refinement
;
All H atoms were treated as riding with C---H distances of
 0.95 (CAr---H), 0.98 (CH₃), and Uiso(H) = 1.2 Ueq(C)
 [1.5 Ueq for methyl hydrogen atoms].
 Riding methyl hydrogen atoms were allowed to rotate freely
 during refinement.
;


#=====================================================================
# 5. Chemical Data 
_chemical_name_systematic 
; 
 2,7-Dimethoxy-5,10-bis(p-anisyl)-5,10-dihydrophenazine  tricyanomethanide
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          'C28 H26 N2 O4, C4 N3 ' 
_chemical_formula_sum 
 'C32 H26 N5 O4' 
_chemical_formula_weight          544.58 
 
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' 
 
_symmetry_cell_setting            'Monoclinic'
_symmetry_space_group_name_H-M    'C2/c' 
_symmetry_space_group_name_Hall     '-C 2yc' 

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' 
 
_cell_length_a                    16.4791(9) 
_cell_length_b                    21.8079(12) 
_cell_length_c                    7.8598(4) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  104.85(3)
_cell_angle_gamma                 90.00 
_cell_volume                      2730.2(3) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     173(2) 
_cell_measurement_reflns_used     ? 
_cell_measurement_theta_min       ? 
_cell_measurement_theta_max       ? 
 
_exptl_crystal_description        'transparent block' 
_exptl_crystal_colour             'colorless'
_exptl_crystal_size_max           0.60 
_exptl_crystal_size_mid           0.40
_exptl_crystal_size_min           0.32
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.325 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              1140 
_exptl_absorpt_coefficient_mu     0.090 
_exptl_absorpt_correction_type    'none' 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
_exptl_absorpt_process_details    ? 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       173(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Bruker Apex CCD' 
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          '453' 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   'variable' 
_diffrn_standards_decay_%         'none'
_diffrn_reflns_number             7248 
_diffrn_reflns_av_R_equivalents   0.0337 
_diffrn_reflns_av_sigmaI/netI     0.0436 
_diffrn_reflns_limit_h_min        -19 
_diffrn_reflns_limit_h_max        10 
_diffrn_reflns_limit_k_min        -26 
_diffrn_reflns_limit_k_max        25 
_diffrn_reflns_limit_l_min        -9 
_diffrn_reflns_limit_l_max        9 
_diffrn_reflns_theta_min          1.58 
_diffrn_reflns_theta_max          25.35 
_reflns_number_total              2497 
_reflns_number_gt                 1834 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'Bruker SMART v5.625 (Bruker, 2001a)'
_computing_cell_refinement        'Bruker SMART v5.625 (Bruker, 2001a)'
_computing_data_reduction         
;
Bruker SAINT v6.36A (Bruker, 2002), Bruker XPREP v6.12 (Bruker, 2001b)
;
_computing_structure_solution     'Bruker SHELXTL v6.14 (Bruker, 2000)' 
_computing_structure_refinement   'Bruker SHELXTL v6.14 (Bruker, 2000)' 
_computing_publication_material   'X-SEED, Barbour, 2001'
_computing_molecular_graphics    'X-SEED, Barbour, 2001'
 
_refine_special_details 
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
; 
 
_refine_ls_structure_factor_coef  Fsqd  
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc  
_refine_ls_weighting_details 
 'calc w=1/[σ²(Fo²)+(0.0871P)²+1.4252P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          2497 
_refine_ls_number_parameters      189 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0833 
_refine_ls_R_factor_gt            0.0574 
_refine_ls_wR_factor_ref          0.1652 
_refine_ls_wR_factor_gt           0.1461 
_refine_ls_goodness_of_fit_ref    1.104 
_refine_ls_restrained_S_all       1.104 
_refine_ls_shift/su_max           0.000 
_refine_ls_shift/su_mean          0.000 
 
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 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
O1 O 0.40583(11) 0.44784(7) 1.1568(2) 0.0414(5) Uani 1 1 d . . . 
O2 O 0.10497(11) 0.44138(8) 0.2786(2) 0.0416(5) Uani 1 1 d . . . 
N1 N 0.22241(12) 0.28707(8) 0.8532(2) 0.0268(5) Uani 1 1 d . . . 
N2 N 0.08789(16) 0.29346(11) 0.0779(3) 0.0510(7) Uani 1 1 d . . . 
N3 N 0.0000 0.11722(14) 0.2500 0.0601(11) Uani 1 2 d S . . 
C1 C 0.37274(15) 0.39037(10) 1.1416(3) 0.0313(6) Uani 1 1 d . . . 
C2 C 0.31359(14) 0.36920(10) 0.9966(3) 0.0298(5) Uani 1 1 d . . . 
H2 H 0.2942 0.3949 0.8968 0.036 Uiso 1 1 calc R . . 
C3 C 0.28189(14) 0.30914(10) 0.9973(3) 0.0274(5) Uani 1 1 d . . . 
C4 C 0.18949(15) 0.22819(9) 0.8535(3) 0.0263(5) Uani 1 1 d . . . 
C5 C 0.12841(15) 0.20586(10) 0.7093(3) 0.0303(6) Uani 1 1 d . . . 
H5 H 0.1079 0.2313 0.6094 0.036 Uiso 1 1 calc R . . 
C6 C 0.09757(15) 0.14716(11) 0.7109(3) 0.0324(6) Uani 1 1 d . . . 
H6 H 0.0562 0.1322 0.6121 0.039 Uiso 1 1 calc R . . 
C7 C 0.19235(15) 0.32607(10) 0.7012(3) 0.0276(5) Uani 1 1 d . . . 
C8 C 0.23968(16) 0.33282(11) 0.5822(3) 0.0332(6) Uani 1 1 d . . . 
H8 H 0.2912 0.3112 0.5985 0.040 Uiso 1 1 calc R . . 
C9 C 0.21234(16) 0.37125(11) 0.4375(3) 0.0335(6) Uani 1 1 d . . . 
H9 H 0.2451 0.3762 0.3551 0.040 Uiso 1 1 calc R . . 
C10 C 0.13678(15) 0.40224(10) 0.4147(3) 0.0314(6) Uani 1 1 d . . . 
C11 C 0.08904(16) 0.39469(11) 0.5343(3) 0.0366(6) Uani 1 1 d . . . 
H11 H 0.0371 0.4157 0.5175 0.044 Uiso 1 1 calc R . . 
C12 C 0.11670(15) 0.35667(11) 0.6785(3) 0.0338(6) Uani 1 1 d . . . 
H12 H 0.0841 0.3516 0.7612 0.041 Uiso 1 1 calc R . . 
C13 C 0.3849(2) 0.48670(12) 1.0056(4) 0.0515(8) Uani 1 1 d . . . 
H13A H 0.4007 0.4665 0.9074 0.077 Uiso 1 1 calc R . . 
H13B H 0.4153 0.5256 1.0324 0.077 Uiso 1 1 calc R . . 
H13C H 0.3244 0.4946 0.9733 0.077 Uiso 1 1 calc R . . 
C14 C 0.14888(19) 0.44620(12) 0.1443(3) 0.0450(7) Uani 1 1 d . . . 
H14A H 0.2039 0.4651 0.1934 0.067 Uiso 1 1 calc R . . 
H14B H 0.1164 0.4716 0.0479 0.067 Uiso 1 1 calc R . . 
H14C H 0.1565 0.4052 0.0996 0.067 Uiso 1 1 calc R . . 
C15 C 0.04844(17) 0.26742(11) 0.1551(3) 0.0354(6) Uani 1 1 d . . . 
C16 C 0.0000 0.23530(15) 0.2500 0.0332(8) Uani 1 2 d S . . 
C17 C 0.0000 0.17062(17) 0.2500 0.0403(9) Uani 1 2 d S . . 
 
 
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
 
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 
O1 C1 1.360(3) . ? 
O1 C13 1.428(3) . ? 
O2 C10 1.364(3) . ? 
O2 C14 1.428(3) . ? 
N1 C3 1.381(3) . y 
N1 C4 1.394(3) . y 
N1 C7 1.447(3) . y 
N2 C15 1.147(3) . y 
N3 C17 1.165(5) . y 
C1 C2 1.375(3) . ? 
C1 C6 1.401(3) 7_557 ? 
C2 C3 1.411(3) . ? 
C2 H2 0.9500 . ? 
C3 C4 1.406(3) 7_557 y 
C4 C5 1.396(3) . ? 
C4 C3 1.406(3) 7_557 ? 
C5 C6 1.378(3) . ? 
C5 H5 0.9500 . ? 
C6 C1 1.401(3) 7_557 ? 
C6 H6 0.9500 . ? 
C7 C8 1.371(3) . ? 
C7 C12 1.385(3) . ? 
C8 C9 1.391(3) . ? 
C8 H8 0.9500 . ? 
C9 C10 1.387(3) . ? 
C9 H9 0.9500 . ? 
C10 C11 1.381(4) . ? 
C11 C12 1.384(3) . ? 
C11 H11 0.9500 . ? 
C12 H12 0.9500 . ? 
C13 H13A 0.9800 . ? 
C13 H13B 0.9800 . ? 
C13 H13C 0.9800 . ? 
C14 H14A 0.9800 . ? 
C14 H14B 0.9800 . ? 
C14 H14C 0.9800 . ? 
C15 C16 1.410(3) . y
C16 C15 1.410(3) 2 ? 
C16 C17 1.411(5) . y 
 
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 O1 C13 117.89(18) . . ? 
C10 O2 C14 117.4(2) . . ? 
C3 N1 C4 120.97(18) . . y 
C3 N1 C7 119.56(18) . . y 
C4 N1 C7 119.45(17) . . y 
O1 C1 C2 124.4(2) . . ? 
O1 C1 C6 114.7(2) . 7_557 ? 
C2 C1 C6 120.8(2) . 7_557 ? 
C1 C2 C3 119.5(2) . . ? 
C1 C2 H2 120.2 . . ? 
C3 C2 H2 120.2 . . ? 
N1 C3 C4 119.9(2) . 7_557 y 
N1 C3 C2 120.4(2) . . ? 
C4 C3 C2 119.7(2) 7_557 . ? 
N1 C4 C5 121.3(2) . . ? 
N1 C4 C3 119.15(19) . 7_557 ? 
C5 C4 C3 119.5(2) . 7_557 ? 
C6 C5 C4 120.5(2) . . ? 
C6 C5 H5 119.8 . . ? 
C4 C5 H5 119.8 . . ? 
C5 C6 C1 119.9(2) . 7_557 ? 
C5 C6 H6 120.0 . . ? 
C1 C6 H6 120.0 7_557 . ? 
C8 C7 C12 120.8(2) . . ? 
C8 C7 N1 119.5(2) . . ? 
C12 C7 N1 119.7(2) . . ? 
C7 C8 C9 120.0(2) . . ? 
C7 C8 H8 120.0 . . ? 
C9 C8 H8 120.0 . . ? 
C10 C9 C8 119.4(2) . . ? 
C10 C9 H9 120.3 . . ? 
C8 C9 H9 120.3 . . ? 
O2 C10 C11 115.9(2) . . ? 
O2 C10 C9 123.9(2) . . ? 
C11 C10 C9 120.2(2) . . ? 
C10 C11 C12 120.2(2) . . ? 
C10 C11 H11 119.9 . . ? 
C12 C11 H11 119.9 . . ? 
C11 C12 C7 119.4(2) . . ? 
C11 C12 H12 120.3 . . ? 
C7 C12 H12 120.3 . . ? 
O1 C13 H13A 109.5 . . ? 
O1 C13 H13B 109.5 . . ? 
H13A C13 H13B 109.5 . . ? 
O1 C13 H13C 109.5 . . ? 
H13A C13 H13C 109.5 . . ? 
H13B C13 H13C 109.5 . . ? 
O2 C14 H14A 109.5 . . ? 
O2 C14 H14B 109.5 . . ? 
H14A C14 H14B 109.5 . . ? 
O2 C14 H14C 109.5 . . ? 
H14A C14 H14C 109.5 . . ? 
H14B C14 H14C 109.5 . . ? 
N2 C15 C16 179.9(3) . . ? 
C15 C16 C15 120.4(3) 2 . y 
C15 C16 C17 119.78(15) 2 . y 
C15 C16 C17 119.78(15) . . y 
N3 C17 C16 180.0 . . ? 
 
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 
C13 O1 C1 C2 -7.2(4) . . . . Y 
C13 O1 C1 C6 173.9(2) . . . 7_557 ? 
O1 C1 C2 C3 -178.2(2) . . . . ? 
C6 C1 C2 C3 0.6(4) 7_557 . . . ? 
C4 N1 C3 C4 0.5(4) . . . 7_557 ? 
C7 N1 C3 C4 179.1(2) . . . 7_557 ? 
C4 N1 C3 C2 -178.8(2) . . . . ? 
C7 N1 C3 C2 -0.3(3) . . . . ? 
C1 C2 C3 N1 179.9(2) . . . . ? 
C1 C2 C3 C4 0.6(4) . . . 7_557 ? 
C3 N1 C4 C5 179.0(2) . . . . ? 
C7 N1 C4 C5 0.5(3) . . . . ? 
C3 N1 C4 C3 -0.5(4) . . . 7_557 ? 
C7 N1 C4 C3 -179.1(2) . . . 7_557 ? 
N1 C4 C5 C6 179.0(2) . . . . ? 
C3 C4 C5 C6 -1.5(4) 7_557 . . . ? 
C4 C5 C6 C1 0.3(4) . . . 7_557 ? 
C3 N1 C7 C8 80.2(3) . . . . Y 
C4 N1 C7 C8 -101.2(3) . . . . ? 
C3 N1 C7 C12 -99.1(3) . . . . ? 
C4 N1 C7 C12 79.5(3) . . . . ? 
C12 C7 C8 C9 0.7(3) . . . . ? 
N1 C7 C8 C9 -178.6(2) . . . . ? 
C7 C8 C9 C10 -0.4(3) . . . . ? 
C14 O2 C10 C11 -174.7(2) . . . . ? 
C14 O2 C10 C9 5.7(3) . . . . Y 
C8 C9 C10 O2 179.3(2) . . . . ? 
C8 C9 C10 C11 -0.3(3) . . . . ? 
O2 C10 C11 C12 -179.0(2) . . . . ? 
C9 C10 C11 C12 0.7(4) . . . . ? 
C10 C11 C12 C7 -0.4(4) . . . . ? 
C8 C7 C12 C11 -0.3(3) . . . . ? 
N1 C7 C12 C11 178.9(2) . . . . ? 
N2 C15 C16 C15 -178(100) . . . 2 ? 
N2 C15 C16 C17 2(100) . . . . ? 
C15 C16 C17 N3 -144(100) 2 . . . ? 
C15 C16 C17 N3 36(100) . . . . ? 
 


_diffrn_measured_fraction_theta_max    0.994 
_diffrn_reflns_theta_full              25.35 
_diffrn_measured_fraction_theta_full   0.994 
_refine_diff_density_max    0.216 
_refine_diff_density_min   -0.417 
_refine_diff_density_rms    0.075 
