#------------------------------------------------------------------------------
#$Date: 2018-10-05 14:19:55 +0200 (vie 05 de oct de 2018) $
#$Revision: 211332 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/61/7216104.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_7216104
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         'C17 H16 N4, 0.5(C12 H8 N2)'
_chemical_formula_sum            'C23 H20 N5'
_chemical_formula_weight         366.44
_chemical_melting_point          165.5(5)
_chemical_name_common
'N,N'-Bis(2-pyridyl)-1,3-diamino-2-methylbenzene phenazine 2:1'
_chemical_name_systematic
;
N,N'-Bis(2-pyridyl)-1,3-diamino-2-methylbenzene phenazine 2:1
;
_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                99.694(7)
_cell_angle_beta                 93.711(6)
_cell_angle_gamma                115.471(9)
_cell_formula_units_Z            2
_cell_length_a                   8.5174(7)
_cell_length_b                   8.6054(9)
_cell_length_c                   14.5408(11)
_cell_measurement_reflns_used    4828
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      4
_cell_volume                     937.12(17)
_computing_cell_refinement       'KM4RED, Version 1.157a, 1999'
_computing_data_reduction        'KM4RED, Version 1.157a, 1999'
_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      140(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Kuma KM4CCD diffractometer'
_diffrn_measurement_method       'ο scan'
_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  0.0500
_diffrn_reflns_av_sigmaI/netI    0.0573
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7115
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.68
_diffrn_standards_decay_%        negligible
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             386
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.010(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3309
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0475
_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)+(0.0800P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1192
_refine_ls_wR_factor_ref         0.1285
_reflns_number_gt                2469
_reflns_number_total             3309
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b503023d.txt
_cod_data_source_block           4-phz
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '165-166' was changed to '165.5(5)' -
the average value was taken and precision was
estimated.

'_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_sg_symbol_Hall     -P1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7216104
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 0.10925(17) 0.31351(16) 0.22165(9) 0.0252(3) Uani 1 1 d .
C2 C 0.10533(19) 0.4646(2) 0.21409(11) 0.0234(4) Uani 1 1 d .
C3 C 0.0937(2) 0.5800(2) 0.29163(11) 0.0249(4) Uani 1 1 d .
H3 H 0.0854 0.6841 0.2821 0.027(4) Uiso 1 1 d R
C4 C 0.0863(2) 0.5351(2) 0.37774(12) 0.0282(4) Uani 1 1 d .
H4 H 0.0790 0.6137 0.4307 0.030(4) Uiso 1 1 d R
C5 C 0.0897(2) 0.3783(2) 0.38677(11) 0.0286(4) Uani 1 1 d .
H5 H 0.0927 0.3465 0.4468 0.034(5) Uiso 1 1 d R
C6 C 0.1007(2) 0.2744(2) 0.30763(11) 0.0272(4) Uani 1 1 d .
H6 H 0.1072 0.1666 0.3103 0.023(4) Uiso 1 1 d R
N7 N 0.11283(17) 0.50693(17) 0.12731(9) 0.0265(3) Uani 1 1 d .
H7 H 0.1538 0.6230 0.1293 0.056(6) Uiso 1 1 d R
C8 C 0.1101(2) 0.3952(2) 0.04296(11) 0.0238(4) Uani 1 1 d .
C9 C -0.0381(2) 0.2347(2) 0.00534(11) 0.0229(4) Uani 1 1 d .
C10 C -0.0336(2) 0.1345(2) -0.07993(11) 0.0236(4) Uani 1 1 d .
C11 C 0.1121(2) 0.1933(2) -0.12696(12) 0.0293(4) Uani 1 1 d .
H11 H 0.1120 0.1229 -0.1857 0.020(4) Uiso 1 1 d R
C12 C 0.2553(2) 0.3533(2) -0.08923(12) 0.0317(4) Uani 1 1 d .
H12 H 0.3553 0.3923 -0.1217 0.043(5) Uiso 1 1 d R
C13 C 0.2548(2) 0.4539(2) -0.00475(12) 0.0287(4) Uani 1 1 d .
H13 H 0.3542 0.5649 0.0228 0.028(4) Uiso 1 1 d R
N14 N -0.18041(17) -0.03088(17) -0.12079(9) 0.0267(3) Uani 1 1 d .
H14 H -0.1592 -0.1252 -0.1358 0.039(5) Uiso 1 1 d R
C15 C -0.3283(2) -0.0429(2) -0.17172(11) 0.0241(4) Uani 1 1 d .
N16 N -0.33814(17) 0.10746(16) -0.17482(9) 0.0269(3) Uani 1 1 d .
C17 C -0.4830(2) 0.0948(2) -0.22564(12) 0.0304(4) Uani 1 1 d .
H17 H -0.4860 0.2047 -0.2270 0.033(5) Uiso 1 1 d R
C18 C -0.6191(2) -0.0600(2) -0.27377(12) 0.0332(4) Uani 1 1 d .
H18 H -0.7160 -0.0568 -0.3096 0.033(5) Uiso 1 1 d R
C19 C -0.6092(2) -0.2154(2) -0.26848(13) 0.0348(4) Uani 1 1 d .
H19 H -0.7023 -0.3277 -0.3006 0.043(5) Uiso 1 1 d R
C20 C -0.4642(2) -0.2083(2) -0.21748(12) 0.0299(4) Uani 1 1 d .
H20 H -0.4507 -0.3123 -0.2137 0.028(4) Uiso 1 1 d R
C21 C -0.1978(2) 0.1719(2) 0.05313(12) 0.0291(4) Uani 1 1 d .
H21A H -0.2009 0.0863 0.0885 0.071(7) Uiso 1 1 d R
H21B H -0.3044 0.1085 0.0085 0.043(5) Uiso 1 1 d R
H21C H -0.1986 0.2683 0.0970 0.038(5) Uiso 1 1 d R
N1A N 1.02852(17) 0.91140(17) 0.41589(9) 0.0283(4) Uani 1 1 d .
C2A C 0.8662(2) 0.8631(2) 0.43882(11) 0.0249(4) Uani 1 1 d .
C3A C 0.7203(2) 0.7187(2) 0.37938(12) 0.0321(4) Uani 1 1 d .
H3A H 0.7461 0.6653 0.3227 0.026(4) Uiso 1 1 d R
C4A C 0.5560(2) 0.6655(2) 0.40352(13) 0.0384(5) Uani 1 1 d .
H4A H 0.4588 0.5644 0.3642 0.046(5) Uiso 1 1 d R
C5A C 0.5288(2) 0.7561(3) 0.48715(13) 0.0424(5) Uani 1 1 d .
H5A H 0.4123 0.7121 0.5034 0.060(6) Uiso 1 1 d R
C6A C 0.6635(2) 0.8956(2) 0.54519(13) 0.0359(4) Uani 1 1 d .
H6A H 0.6467 0.9554 0.6028 0.041(5) Uiso 1 1 d R
C7A C 0.8381(2) 0.9538(2) 0.52376(11) 0.0271(4) 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 0.0033 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'
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 116.88(13) .
N1 C2 N7 118.04(14) .
N1 C2 C3 122.50(14) .
N7 C2 C3 119.46(13) .
C4 C3 C2 118.49(14) .
C4 C3 H3 122.0 .
C2 C3 H3 119.5 .
C3 C4 C5 119.75(15) .
C3 C4 H4 118.7 .
C5 C4 H4 121.6 .
C6 C5 C4 117.68(15) .
C6 C5 H5 120.3 .
C4 C5 H5 121.9 .
N1 C6 C5 124.70(14) .
N1 C6 H6 114.2 .
C5 C6 H6 121.1 .
C2 N7 C8 124.53(13) .
C2 N7 H7 114.3 .
C8 N7 H7 118.7 .
C13 C8 C9 120.64(15) .
C13 C8 N7 118.37(14) .
C9 C8 N7 120.89(14) .
C10 C9 C8 117.66(14) .
C10 C9 C21 120.60(15) .
C8 C9 C21 121.74(14) .
C11 C10 C9 121.42(15) .
C11 C10 N14 118.67(14) .
C9 C10 N14 119.91(14) .
C12 C11 C10 119.80(15) .
C12 C11 H11 120.1 .
C10 C11 H11 120.1 .
C11 C12 C13 119.89(16) .
C11 C12 H12 119.3 .
C13 C12 H12 120.8 .
C12 C13 C8 120.57(15) .
C12 C13 H13 120.8 .
C8 C13 H13 118.6 .
C15 N14 C10 122.08(13) .
C15 N14 H14 115.3 .
C10 N14 H14 117.3 .
N16 C15 N14 117.68(14) .
N16 C15 C20 121.93(14) .
N14 C15 C20 120.38(14) .
C15 N16 C17 117.37(14) .
N16 C17 C18 124.47(15) .
N16 C17 H17 115.5 .
C18 C17 H17 120.0 .
C17 C18 C19 117.67(16) .
C17 C18 H18 119.1 .
C19 C18 H18 123.3 .
C20 C19 C18 119.67(16) .
C20 C19 H19 119.6 .
C18 C19 H19 120.8 .
C19 C20 C15 118.87(15) .
C19 C20 H20 122.2 .
C15 C20 H20 118.9 .
C9 C21 H21A 111.8 .
C9 C21 H21B 111.9 .
H21A C21 H21B 102.9 .
C9 C21 H21C 110.6 .
H21A C21 H21C 106.8 .
H21B C21 H21C 112.5 .
C7A N1A C2A 116.93(14) 2_776
N1A C2A C3A 119.72(15) .
N1A C2A C7A 121.10(15) .
C3A C2A C7A 119.18(15) .
C4A C3A C2A 120.10(16) .
C4A C3A H3A 124.2 .
C2A C3A H3A 115.7 .
C3A C4A C5A 120.49(17) .
C3A C4A H4A 119.5 .
C5A C4A H4A 120.0 .
C6A C5A C4A 121.41(17) .
C6A C5A H5A 120.3 .
C4A C5A H5A 118.3 .
C5A C6A C7A 120.09(17) .
C5A C6A H6A 121.9 .
C7A C6A H6A 118.0 .
N1A C7A C6A 119.30(15) 2_776
N1A C7A C2A 121.97(15) 2_776
C6A C7A C2A 118.71(16) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C2 1.3373(19) .
N1 C6 1.347(2) .
C2 N7 1.369(2) .
C2 C3 1.411(2) .
C3 C4 1.369(2) .
C3 H3 0.9600 .
C4 C5 1.389(2) .
C4 H4 0.9599 .
C5 C6 1.368(2) .
C5 H5 0.9600 .
C6 H6 0.9600 .
N7 C8 1.4176(19) .
N7 H7 0.9000 .
C8 C13 1.396(2) .
C8 C9 1.399(2) .
C9 C10 1.399(2) .
C9 C21 1.498(2) .
C10 C11 1.397(2) .
C10 N14 1.4247(19) .
C11 C12 1.378(2) .
C11 H11 0.9600 .
C12 C13 1.380(2) .
C12 H12 0.9599 .
C13 H13 0.9600 .
N14 C15 1.3741(19) .
N14 H14 0.9001 .
C15 N16 1.3397(19) .
C15 C20 1.405(2) .
N16 C17 1.349(2) .
C17 C18 1.364(2) .
C17 H17 0.9600 .
C18 C19 1.391(2) .
C18 H18 0.9600 .
C19 C20 1.371(2) .
C19 H19 0.9600 .
C20 H20 0.9599 .
C21 H21A 0.9600 .
C21 H21B 0.9600 .
C21 H21C 0.9600 .
N1A C7A 1.342(2) 2_776
N1A C2A 1.344(2) .
C2A C3A 1.417(2) .
C2A C7A 1.438(2) .
C3A C4A 1.363(2) .
C3A H3A 0.9600 .
C4A C5A 1.418(3) .
C4A H4A 0.9600 .
C5A C6A 1.349(3) .
C5A H5A 0.9600 .
C6A C7A 1.425(2) .
C6A H6A 0.9600 .
C7A N1A 1.342(2) 2_776
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 N16 0.90 2.12 2.9581(19) 154.4 2_565
N14 H14 N1 0.90 2.09 2.9351(18) 157.1 2
