#------------------------------------------------------------------------------
#$Date: 2018-10-05 14:19:55 +0200 (vie 05 de oct de 2018) $
#$Revision: 211332 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/61/7216101.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_7216101
loop_
_publ_author_name
'Gdaniec, Maria'
'Bensemann, Igor'
'Połoński, Tadeusz'
_publ_section_title
;
 Interplay of hydrogen bonding and aromatic ring interactions in
 supramolecular complexes of phenazine with
 N,N′-bis(2-pyridyl)aryldiamines
;
_journal_issue                   71
_journal_name_full               CrystEngComm
_journal_page_first              433
_journal_paper_doi               10.1039/b503023d
_journal_volume                  7
_journal_year                    2005
_chemical_formula_moiety         'C16 H14 N4, 4(C12 H8 N2)'
_chemical_formula_sum            'C64 H46 N12'
_chemical_formula_weight         983.13
_chemical_melting_point          171
_chemical_name_common
'N,N'-Bis(2-pyridyl)-1,4-diaminobenzene phenazine 1:4 complex'
_chemical_name_systematic
;
N,N'-Bis(2-pyridyl)-1,4-diaminobenzene phenazine 1:4 complex
;
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                108.446(7)
_cell_angle_beta                 101.895(7)
_cell_angle_gamma                93.506(7)
_cell_formula_units_Z            1
_cell_length_a                   9.8663(9)
_cell_length_b                   10.7948(9)
_cell_length_c                   12.5957(9)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28
_cell_measurement_theta_min      11
_cell_volume                     1233.66(19)
_computing_cell_refinement       'Kuma KM-4 software (Kuma Diffraction, 1991)'
_computing_data_collection       'Kuma KM-4 sofware (Kuma Diffraction, 1991)'
_computing_data_reduction        'Kuma KM-4 software (Kuma Diffraction, 1991)'
_computing_molecular_graphics
; 'Stereochemical Workstation (Siemens
Analytical X-Ray Instruments, Inc., 1989)'
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'KM-4 four-circle diffractometer'
_diffrn_measurement_method       'ω/2θ scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0155
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4348
_diffrn_reflns_theta_full        66.59
_diffrn_reflns_theta_max         66.59
_diffrn_reflns_theta_min         3.81
_diffrn_standards_decay_%        <1.5
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.637
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             514
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0048(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         4339
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0391
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0617P)²+0.1403P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1119
_reflns_number_gt                3580
_reflns_number_total             4339
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b503023d.txt
_cod_data_source_block           1-phz
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_hydrogen_treatment' value 'refu' changed to 'refU'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'difmap,geom' was changed to
'mixed'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_cell_volume        1233.66(18)
_cod_original_sg_symbol_Hall     -P1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7216101
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
N1 N 0.38482(11) -0.12354(11) 0.03664(9) 0.0523(3) Uani 1 1 d .
C2 C 0.31920(12) -0.16193(11) 0.10549(10) 0.0435(3) Uani 1 1 d .
C3 C 0.37903(14) -0.23424(13) 0.17367(11) 0.0532(3) Uani 1 1 d .
H3 H 0.3285 -0.2577 0.2235 0.064(4) Uiso 1 1 d R
C4 C 0.50900(15) -0.26741(15) 0.16875(13) 0.0641(4) Uani 1 1 d .
H4 H 0.5513 -0.3165 0.2153 0.079(5) Uiso 1 1 d R
C5 C 0.57865(15) -0.22870(15) 0.09725(13) 0.0641(4) Uani 1 1 d .
H5 H 0.6707 -0.2513 0.0941 0.082(5) Uiso 1 1 d R
C6 C 0.51374(14) -0.15734(14) 0.03530(12) 0.0599(4) Uani 1 1 d .
H6 H 0.5580 -0.1281 -0.0153 0.067(4) Uiso 1 1 d R
N7 N 0.18774(10) -0.13035(11) 0.11231(9) 0.0501(3) Uani 1 1 d .
H7 H 0.1511 -0.1548 0.1636 0.055(4) Uiso 1 1 d R
C8 C 0.09888(12) -0.06367(11) 0.05413(9) 0.0418(3) Uani 1 1 d .
C9 C -0.02502(13) -0.03806(12) 0.08815(10) 0.0460(3) Uani 1 1 d .
H9 H -0.0432 -0.0651 0.1501 0.048(3) Uiso 1 1 d R
C10 C 0.12269(13) -0.02406(12) -0.03624(10) 0.0457(3) Uani 1 1 d .
H10 H 0.2087 -0.0378 -0.0598 0.047(3) Uiso 1 1 d R
N1A N 0.55680(13) 0.41239(11) 0.62061(10) 0.0584(3) Uani 1 1 d .
C2A C 0.68130(16) 0.48825(13) 0.66580(11) 0.0550(3) Uani 1 1 d .
C3A C 0.7147(2) 0.57103(16) 0.78302(13) 0.0716(4) Uani 1 1 d .
H3A H 0.6418 0.5697 0.8228 0.081(5) Uiso 1 1 d R
C4A C 0.8387(2) 0.65087(17) 0.82878(14) 0.0823(5) Uani 1 1 d .
H4A H 0.8635 0.7051 0.9086 0.099(6) Uiso 1 1 d R
C5A C 0.9373(2) 0.65231(16) 0.76230(16) 0.0781(5) Uani 1 1 d .
H5A H 1.0257 0.7075 0.7974 0.105(7) Uiso 1 1 d R
C6A C 0.91074(17) 0.57463(15) 0.65086(15) 0.0673(4) Uani 1 1 d .
H6A H 0.9762 0.5693 0.6033 0.093(6) Uiso 1 1 d R
C7A C 0.78196(15) 0.49000(13) 0.59884(12) 0.0534(3) Uani 1 1 d .
N8A N 0.75682(13) 0.41367(11) 0.48785(10) 0.0566(3) Uani 1 1 d .
C9A C 0.63189(16) 0.33818(12) 0.44287(11) 0.0541(3) Uani 1 1 d .
C10A C 0.5975(2) 0.25571(15) 0.32499(13) 0.0694(4) Uani 1 1 d .
H10A H 0.6703 0.2596 0.2855 0.079(5) Uiso 1 1 d R
C11A C 0.4713(2) 0.17974(16) 0.27872(14) 0.0810(5) Uani 1 1 d .
H11A H 0.4455 0.1255 0.1989 0.112(7) Uiso 1 1 d R
C12A C 0.3714(2) 0.18162(16) 0.34396(15) 0.0782(5) Uani 1 1 d .
H12A H 0.2806 0.1310 0.3082 0.090(6) Uiso 1 1 d R
C13A C 0.39908(17) 0.25765(15) 0.45563(14) 0.0678(4) Uani 1 1 d .
H13A H 0.3299 0.2606 0.4997 0.098(6) Uiso 1 1 d R
C14A C 0.53058(15) 0.33776(13) 0.50928(12) 0.0536(3) Uani 1 1 d .
N1B N 0.91824(11) 0.22876(10) 0.71159(9) 0.0500(3) Uani 1 1 d .
C2B C 1.03157(13) 0.32089(12) 0.75471(11) 0.0476(3) Uani 1 1 d .
C3B C 1.06938(15) 0.39370(14) 0.87422(12) 0.0581(3) Uani 1 1 d .
H3B H 1.0121 0.3712 0.9202 0.075(5) Uiso 1 1 d R
C4B C 1.18051(17) 0.48909(15) 0.91823(13) 0.0659(4) Uani 1 1 d .
H4B H 1.2106 0.5367 0.9994 0.084(5) Uiso 1 1 d R
C5B C 1.26176(16) 0.51732(15) 0.84644(14) 0.0659(4) Uani 1 1 d .
H5B H 1.3416 0.5843 0.8784 0.086(5) Uiso 1 1 d R
C6B C 1.23145(14) 0.44870(14) 0.73208(13) 0.0580(3) Uani 1 1 d .
H6B H 1.2863 0.4637 0.6815 0.063(4) Uiso 1 1 d R
C7B C 1.11523(13) 0.34736(12) 0.68221(11) 0.0482(3) Uani 1 1 d .
N8B N 1.08614(12) 0.27981(11) 0.56897(9) 0.0524(3) Uani 1 1 d .
C9B C 0.97177(14) 0.18964(12) 0.52583(11) 0.0499(3) Uani 1 1 d .
C10B C 0.93364(17) 0.11629(15) 0.40591(12) 0.0626(4) Uani 1 1 d .
H10B H 0.9949 0.1368 0.3619 0.078(5) Uiso 1 1 d R
C11B C 0.81729(18) 0.02794(16) 0.36103(14) 0.0710(4) Uani 1 1 d .
H11B H 0.7929 -0.0179 0.2794 0.091(6) Uiso 1 1 d R
C12B C 0.73085(17) 0.00472(16) 0.43118(14) 0.0694(4) Uani 1 1 d .
H12B H 0.6491 -0.0600 0.3967 0.089(5) Uiso 1 1 d R
C13B C 0.76378(15) 0.07005(14) 0.54572(13) 0.0609(4) Uani 1 1 d .
H13B H 0.7070 0.0573 0.5958 0.075(5) Uiso 1 1 d R
C14B C 0.88557(14) 0.16480(12) 0.59749(11) 0.0489(3) Uani 1 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 0.0181 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'
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
C2 N1 C6 116.56(11) .
N1 C2 N7 120.03(11) .
N1 C2 C3 122.64(11) .
N7 C2 C3 117.33(10) .
C4 C3 C2 118.82(12) .
C4 C3 H3 121.6 .
C2 C3 H3 119.6 .
C3 C4 C5 119.33(13) .
C3 C4 H4 119.6 .
C5 C4 H4 121.0 .
C6 C5 C4 117.99(13) .
C6 C5 H5 122.5 .
C4 C5 H5 119.5 .
N1 C6 C5 124.65(13) .
N1 C6 H6 114.4 .
C5 C6 H6 121.0 .
C2 N7 C8 131.36(10) .
C2 N7 H7 115.8 .
C8 N7 H7 112.9 .
C9 C8 C10 117.49(11) .
C9 C8 N7 116.93(10) .
C10 C8 N7 125.56(11) .
C10 C9 C8 122.67(10) 2
C10 C9 H9 118.8 2
C8 C9 H9 118.5 .
C9 C10 C8 119.84(11) 2
C9 C10 H10 120.9 2
C8 C10 H10 119.3 .
C14A N1A C2A 116.77(12) .
N1A C2A C3A 119.52(14) .
N1A C2A C7A 121.96(12) .
C3A C2A C7A 118.51(14) .
C4A C3A C2A 120.04(16) .
C4A C3A H3A 124.7 .
C2A C3A H3A 115.1 .
C3A C4A C5A 121.15(16) .
C3A C4A H4A 120.6 .
C5A C4A H4A 118.2 .
C6A C5A C4A 120.97(16) .
C6A C5A H5A 119.4 .
C4A C5A H5A 119.6 .
C5A C6A C7A 119.97(16) .
C5A C6A H6A 123.9 .
C7A C6A H6A 116.0 .
N8A C7A C6A 119.31(14) .
N8A C7A C2A 121.35(13) .
C6A C7A C2A 119.35(14) .
C7A N8A C9A 116.48(12) .
N8A C9A C10A 119.49(13) .
N8A C9A C14A 122.18(12) .
C10A C9A C14A 118.33(14) .
C11A C10A C9A 119.87(16) .
C11A C10A H10A 125.9 .
C9A C10A H10A 114.2 .
C10A C11A C12A 121.45(15) .
C10A C11A H11A 120.9 .
C12A C11A H11A 117.6 .
C13A C12A C11A 120.87(16) .
C13A C12A H12A 119.0 .
C11A C12A H12A 120.1 .
C12A C13A C14A 120.15(16) .
C12A C13A H13A 120.8 .
C14A C13A H13A 119.0 .
N1A C14A C13A 119.45(13) .
N1A C14A C9A 121.25(13) .
C13A C14A C9A 119.30(13) .
C14B N1B C2B 117.15(10) .
N1B C2B C3B 119.67(11) .
N1B C2B C7B 121.28(12) .
C3B C2B C7B 119.04(12) .
C4B C3B C2B 120.35(13) .
C4B C3B H3B 123.2 .
C2B C3B H3B 116.4 .
C3B C4B C5B 120.75(14) .
C3B C4B H4B 121.7 .
C5B C4B H4B 117.5 .
C6B C5B C4B 121.10(14) .
C6B C5B H5B 118.5 .
C4B C5B H5B 120.4 .
C5B C6B C7B 119.95(13) .
C5B C6B H6B 123.1 .
C7B C6B H6B 116.9 .
N8B C7B C6B 119.54(12) .
N8B C7B C2B 121.68(12) .
C6B C7B C2B 118.78(12) .
C9B N8B C7B 116.91(11) .
N8B C9B C10B 119.70(12) .
N8B C9B C14B 121.69(12) .
C10B C9B C14B 118.61(12) .
C11B C10B C9B 120.33(14) .
C11B C10B H10B 124.4 .
C9B C10B H10B 115.2 .
C10B C11B C12B 121.19(14) .
C10B C11B H11B 118.3 .
C12B C11B H11B 120.5 .
C13B C12B C11B 120.75(14) .
C13B C12B H12B 120.0 .
C11B C12B H12B 119.2 .
C12B C13B C14B 120.29(13) .
C12B C13B H13B 122.9 .
C14B C13B H13B 116.8 .
N1B C14B C13B 119.98(12) .
N1B C14B C9B 121.21(12) .
C13B C14B C9B 118.80(12) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C2 1.3301(15) .
N1 C6 1.3465(17) .
C2 N7 1.3738(15) .
C2 C3 1.4024(17) .
C3 C4 1.3606(19) .
C3 H3 0.9600 .
C4 C5 1.384(2) .
C4 H4 0.9601 .
C5 C6 1.359(2) .
C5 H5 0.9600 .
C6 H6 0.9600 .
N7 C8 1.4035(15) .
N7 H7 0.9000 .
C8 C9 1.3916(16) .
C8 C10 1.3927(15) .
C9 C10 1.3792(17) 2
C9 H9 0.9602 .
C10 C9 1.3792(17) 2
C10 H10 0.9600 .
N1A C14A 1.3388(18) .
N1A C2A 1.3406(18) .
C2A C3A 1.420(2) .
C2A C7A 1.432(2) .
C3A C4A 1.356(3) .
C3A H3A 0.9600 .
C4A C5A 1.410(3) .
C4A H4A 0.9600 .
C5A C6A 1.349(2) .
C5A H5A 0.9600 .
C6A C7A 1.419(2) .
C6A H6A 0.9599 .
C7A N8A 1.3409(17) .
N8A C9A 1.3421(18) .
C9A C10A 1.4252(19) .
C9A C14A 1.4302(19) .
C10A C11A 1.355(2) .
C10A H10A 0.9600 .
C11A C12A 1.405(3) .
C11A H11A 0.9600 .
C12A C13A 1.345(2) .
C12A H12A 0.9600 .
C13A C14A 1.421(2) .
C13A H13A 0.9600 .
N1B C14B 1.3416(16) .
N1B C2B 1.3439(16) .
C2B C3B 1.4167(18) .
C2B C7B 1.4296(17) .
C3B C4B 1.349(2) .
C3B H3B 0.9599 .
C4B C5B 1.413(2) .
C4B H4B 0.9600 .
C5B C6B 1.354(2) .
C5B H5B 0.9600 .
C6B C7B 1.4216(18) .
C6B H6B 0.9599 .
C7B N8B 1.3402(16) .
N8B C9B 1.3396(17) .
C9B C10B 1.4222(19) .
C9B C14B 1.4322(17) .
C10B C11B 1.343(2) .
C10B H10B 0.9599 .
C11B C12B 1.413(2) .
C11B H11B 0.9600 .
C12B C13B 1.349(2) .
C12B H12B 0.9600 .
C13B C14B 1.4212(19) .
C13B H13B 0.9600 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N7 H7 N1B 0.90 2.18 3.0747(13) 173.3 2_656
