#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/44/7214443.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_7214443
loop_
_publ_author_name
'Chan, Eric J.'
'Grabowsky, Simon'
'Harrowfield, Jack M.'
'Shi, Ming W.'
'Skelton, Brian W.'
'Sobolev, Alexandre N.'
'White, Allan H.'
_publ_section_title
;
 Hirshfeld surface analysis of crystal packing in aza-aromatic picrate
 salts
;
_journal_issue                   21
_journal_name_full               CrystEngComm
_journal_page_first              4508
_journal_paper_doi               10.1039/c4ce00095a
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C6 H2 N3 O7, C12 H9 N2'
_chemical_formula_sum            'C18 H11 N5 O7'
_chemical_formula_weight         409.32
_chemical_name_systematic
;
1,10-Phenanthrolinium picrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 98.116(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.509(5)
_cell_length_b                   7.028(3)
_cell_length_c                   18.804(7)
_cell_measurement_reflns_used    4060
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.5685
_cell_measurement_theta_min      2.4835
_cell_volume                     1767.4(12)
_computing_cell_refinement       'Siemens SAINT (Siemens, 1995)'
_computing_data_collection       'Siemens SMART (Siemens, 1995)'
_computing_data_reduction        'XPREP, Bruker Version 5.1/NT, 1997'
_computing_molecular_graphics
'XP Interactive Molecular Graphics, Bruker AXS V5.1, 1998)'
_computing_publication_material  'XCIF Tables Production, Bruker Ver. 2008/2'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measurement_device_type
;
Bruker SMART CCD diffractometer
;
_diffrn_measurement_method       'ω scans'
_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  0.0589
_diffrn_reflns_av_sigmaI/netI    0.0564
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            14321
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.60
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS (Sheldrick, 1996)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       slab
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         4149
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0528
_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)+(0.0767P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1297
_refine_ls_wR_factor_ref         0.1424
_reflns_number_gt                2679
_reflns_number_total             4149
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce00095a2.cif
_cod_data_source_block           CCDC606099
_cod_depositor_comments
'Adding full bibliography for 7214441--7214449.cif.'
_cod_original_cell_volume        1767.3(12)
_cod_original_sg_symbol_Hall     -P_2ybc
_cod_original_sg_symbol_H-M      P_21/c
_cod_database_code               7214443
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
N011 N 0.65104(12) 0.5053(2) 0.35251(9) 0.0261(4) Uani 1 1 d
H011 H 0.6191(17) 0.487(3) 0.3061(13) 0.044(7) Uiso 1 1 d
C012 C 0.59763(15) 0.4856(3) 0.40767(11) 0.0306(5) Uani 1 1 d
H012 H 0.5250(15) 0.449(3) 0.3951(10) 0.026(5) Uiso 1 1 d
C013 C 0.64411(16) 0.5168(3) 0.47955(12) 0.0347(5) Uani 1 1 d
H013 H 0.6085(15) 0.499(3) 0.5231(11) 0.035(6) Uiso 1 1 d
C014 C 0.74516(16) 0.5715(3) 0.49186(12) 0.0340(5) Uani 1 1 d
H014 H 0.7779(15) 0.590(3) 0.5400(11) 0.035(6) Uiso 1 1 d
C015 C 0.80146(14) 0.5924(3) 0.43297(11) 0.0291(5) Uani 1 1 d
C016 C 0.75144(13) 0.5550(3) 0.36212(10) 0.0253(4) Uani 1 1 d
C017 C 0.90684(15) 0.6494(3) 0.44143(12) 0.0349(5) Uani 1 1 d
H017 H 0.9395(15) 0.677(3) 0.4906(11) 0.039(6) Uiso 1 1 d
N021 N 0.74928(12) 0.5237(2) 0.23316(9) 0.0307(4) Uani 1 1 d
C022 C 0.79816(16) 0.5341(3) 0.17556(12) 0.0343(5) Uani 1 1 d
H022 H 0.7599(18) 0.502(3) 0.1311(13) 0.049(7) Uiso 1 1 d
C023 C 0.90116(16) 0.5888(3) 0.17954(13) 0.0374(5) Uani 1 1 d
H023 H 0.9296(17) 0.597(3) 0.1336(13) 0.050(7) Uiso 1 1 d
C024 C 0.95552(16) 0.6313(3) 0.24613(13) 0.0375(5) Uani 1 1 d
H024 H 1.0270(16) 0.670(3) 0.2522(11) 0.043(6) Uiso 1 1 d
C025 C 0.90754(14) 0.6210(3) 0.30981(11) 0.0306(5) Uani 1 1 d
C026 C 0.80389(14) 0.5661(3) 0.29914(11) 0.0272(4) Uani 1 1 d
C027 C 0.95768(15) 0.6626(3) 0.38280(12) 0.0350(5) Uani 1 1 d
H027 H 1.0290(15) 0.698(3) 0.3880(10) 0.033(5) Uiso 1 1 d
O1 O 0.49309(10) 0.4123(2) 0.25354(8) 0.0347(4) Uani 1 1 d
C1 C 0.41756(14) 0.4631(3) 0.20951(10) 0.0276(4) Uani 1 1 d
C2 C 0.42156(13) 0.4894(3) 0.13144(11) 0.0258(4) Uani 1 1 d
C3 C 0.34121(14) 0.5394(3) 0.07962(11) 0.0271(4) Uani 1 1 d
H3 H 0.3484(14) 0.553(3) 0.0262(11) 0.031(5) Uiso 1 1 d
C4 C 0.24659(13) 0.5709(3) 0.10300(10) 0.0249(4) Uani 1 1 d
C5 C 0.23459(14) 0.5573(3) 0.17597(10) 0.0256(4) Uani 1 1 d
H5 H 0.1666(15) 0.582(3) 0.1926(10) 0.027(5) Uiso 1 1 d
C6 C 0.31626(14) 0.5060(3) 0.22782(10) 0.0260(4) Uani 1 1 d
N2 N 0.51970(12) 0.4603(2) 0.10529(9) 0.0308(4) Uani 1 1 d
O21 O 0.56600(10) 0.3087(2) 0.12108(9) 0.0439(4) Uani 1 1 d
O22 O 0.54968(10) 0.5893(2) 0.06696(8) 0.0386(4) Uani 1 1 d
N4 N 0.15938(12) 0.6185(2) 0.04992(9) 0.0293(4) Uani 1 1 d
O41 O 0.16808(11) 0.6122(2) -0.01556(8) 0.0442(4) Uani 1 1 d
O42 O 0.07908(10) 0.6659(2) 0.07282(8) 0.0377(4) Uani 1 1 d
N6 N 0.29470(12) 0.4887(2) 0.30259(9) 0.0303(4) Uani 1 1 d
O61 O 0.35694(10) 0.4105(2) 0.34916(7) 0.0384(4) Uani 1 1 d
O62 O 0.21209(11) 0.5522(2) 0.31698(8) 0.0436(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'
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
C012 N011 C016 122.95(17)
C012 N011 H011 118.8(14)
C016 N011 H011 118.3(14)
N011 C012 C013 120.05(19)
N011 C012 H012 116.9(11)
C013 C012 H012 123.0(11)
C014 C013 C012 119.1(2)
C014 C013 H013 117.5(12)
C012 C013 H013 123.4(12)
C013 C014 C015 120.6(2)
C013 C014 H014 120.1(12)
C015 C014 H014 119.3(12)
C016 C015 C014 117.85(18)
C016 C015 C017 118.37(18)
C014 C015 C017 123.78(19)
N011 C016 C015 119.47(17)
N011 C016 C026 118.92(17)
C015 C016 C026 121.60(17)
C027 C017 C015 121.1(2)
C027 C017 H017 121.9(12)
C015 C017 H017 117.0(12)
C022 N021 C026 116.71(17)
N021 C022 C023 123.6(2)
N021 C022 H022 115.4(15)
C023 C022 H022 121.0(15)
C024 C023 C022 119.3(2)
C024 C023 H023 123.3(13)
C022 C023 H023 117.4(13)
C023 C024 C025 119.6(2)
C023 C024 H024 122.9(12)
C025 C024 H024 117.5(12)
C026 C025 C024 116.14(19)
C026 C025 C027 119.60(18)
C024 C025 C027 124.26(19)
N021 C026 C025 124.60(18)
N021 C026 C016 117.12(17)
C025 C026 C016 118.28(18)
C017 C027 C025 121.04(19)
C017 C027 H027 121.7(11)
C025 C027 H027 117.2(11)
O1 C1 C2 122.67(17)
O1 C1 C6 125.88(18)
C2 C1 C6 111.45(16)
C3 C2 C1 125.89(17)
C3 C2 N2 116.34(17)
C1 C2 N2 117.77(16)
C2 C3 C4 117.77(18)
C2 C3 H3 122.3(11)
C4 C3 H3 120.0(11)
C5 C4 C3 121.43(17)
C5 C4 N4 119.04(16)
C3 C4 N4 119.53(17)
C4 C5 C6 120.27(17)
C4 C5 H5 121.1(11)
C6 C5 H5 118.6(11)
C5 C6 N6 115.94(16)
C5 C6 C1 123.12(17)
N6 C6 C1 120.89(16)
O21 N2 O22 123.98(17)
O21 N2 C2 118.48(16)
O22 N2 C2 117.51(16)
O41 N4 O42 123.12(16)
O41 N4 C4 118.75(16)
O42 N4 C4 118.12(16)
O61 N6 O62 122.03(16)
O61 N6 C6 119.84(16)
O62 N6 C6 118.12(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N011 C012 1.352(3)
N011 C016 1.387(2)
N011 H011 0.93(2)
C012 C013 1.425(3)
C012 H012 1.010(19)
C013 C014 1.405(3)
C013 H013 1.02(2)
C014 C015 1.437(3)
C014 H014 0.96(2)
C015 C016 1.430(3)
C015 C017 1.466(3)
C016 C026 1.465(3)
C017 C027 1.382(3)
C017 H017 0.99(2)
N021 C022 1.348(3)
N021 C026 1.384(3)
C022 C023 1.435(3)
C022 H022 0.95(2)
C023 C024 1.392(3)
C023 H023 1.00(2)
C024 C025 1.442(3)
C024 H024 0.99(2)
C025 C026 1.439(3)
C025 C027 1.472(3)
C027 H027 0.99(2)
O1 C1 1.271(2)
C1 C2 1.488(3)
C1 C6 1.488(3)
C2 C3 1.397(3)
C2 N2 1.492(2)
C3 C4 1.426(3)
C3 H3 1.03(2)
C4 C5 1.408(3)
C4 N4 1.471(2)
C5 C6 1.412(3)
C5 H5 1.025(19)
C6 N6 1.481(3)
N2 O21 1.250(2)
N2 O22 1.260(2)
N4 O41 1.254(2)
N4 O42 1.267(2)
N6 O61 1.252(2)
N6 O62 1.266(2)
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
N011 H011 O1 0.93(2) 1.92(2) 2.706(2) 141.7(19)
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
C016 N011 C012 C013 0.2(3)
N011 C012 C013 C014 1.2(3)
C012 C013 C014 C015 -1.1(3)
C013 C014 C015 C016 -0.3(3)
C013 C014 C015 C017 179.78(19)
C012 N011 C016 C015 -1.7(3)
C012 N011 C016 C026 177.79(17)
C014 C015 C016 N011 1.7(3)
C017 C015 C016 N011 -178.41(17)
C014 C015 C016 C026 -177.80(17)
C017 C015 C016 C026 2.1(3)
C016 C015 C017 C027 -1.5(3)
C014 C015 C017 C027 178.39(19)
C026 N021 C022 C023 -1.0(3)
N021 C022 C023 C024 1.0(3)
C022 C023 C024 C025 -0.4(3)
C023 C024 C025 C026 -0.1(3)
C023 C024 C025 C027 179.94(19)
C022 N021 C026 C025 0.5(3)
C022 N021 C026 C016 -179.91(17)
C024 C025 C026 N021 0.1(3)
C027 C025 C026 N021 -179.96(18)
C024 C025 C026 C016 -179.54(17)
C027 C025 C026 C016 0.4(3)
N011 C016 C026 N021 -0.7(3)
C015 C016 C026 N021 178.77(16)
N011 C016 C026 C025 178.94(17)
C015 C016 C026 C025 -1.6(3)
C015 C017 C027 C025 0.4(3)
C026 C025 C027 C017 0.1(3)
C024 C025 C027 C017 -179.90(19)
O1 C1 C2 C3 177.99(18)
C6 C1 C2 C3 -2.7(3)
O1 C1 C2 N2 -2.0(3)
C6 C1 C2 N2 177.27(15)
C1 C2 C3 C4 0.8(3)
N2 C2 C3 C4 -179.17(16)
C2 C3 C4 C5 1.7(3)
C2 C3 C4 N4 -178.29(16)
C3 C4 C5 C6 -1.9(3)
N4 C4 C5 C6 178.04(16)
C4 C5 C6 N6 -177.75(16)
C4 C5 C6 C1 -0.3(3)
O1 C1 C6 C5 -178.33(18)
C2 C1 C6 C5 2.4(2)
O1 C1 C6 N6 -1.0(3)
C2 C1 C6 N6 179.73(15)
C3 C2 N2 O21 -127.72(19)
C1 C2 N2 O21 52.3(2)
C3 C2 N2 O22 50.7(2)
C1 C2 N2 O22 -129.34(18)
C5 C4 N4 O41 -173.10(17)
C3 C4 N4 O41 6.9(3)
C5 C4 N4 O42 7.6(2)
C3 C4 N4 O42 -172.45(17)
C5 C6 N6 O61 166.74(17)
C1 C6 N6 O61 -10.8(3)
C5 C6 N6 O62 -12.3(2)
C1 C6 N6 O62 170.19(17)
