#------------------------------------------------------------------------------
#$Date: 2016-03-24 01:30:03 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179532 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/01/4500132.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_4500132
loop_
_publ_author_name
'Bertolasi, Valerio'
'Gilli, Paola'
'Gilli, Gastone'
_publ_section_title
;
 Hydrogen Bonding and Electron Donor−Acceptor (EDA) Interactions
 Controlling the Crystal Packing of Picric Acid and Its Adducts with
 Nitrogen Bases. Their Rationalization in Terms of the pKaEqualization and
 Electron-Pair Saturation Concepts
;
_journal_issue                   7
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2724
_journal_paper_doi               10.1021/cg101007a
_journal_volume                  11
_journal_year                    2011
_chemical_formula_moiety         'C6 H3 N3 O7, C4 H4 N2 O3'
_chemical_formula_sum            'C11 H7 N5 O10'
_chemical_formula_weight         369.22
_chemical_name_systematic
;
4-nitropyridine-N-oxide, picric 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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.4066(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.2140(4)
_cell_length_b                   8.2542(2)
_cell_length_c                   23.4160(7)
_cell_measurement_reflns_used    10664
_cell_measurement_temperature    295
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      3.97
_cell_volume                     2916.03(14)
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1999)'
_computing_publication_material
'SHELXL-97 (Sheldrick, 1997), PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      295
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'φ scans and 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  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0374
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            10664
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.97
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.682
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         2808
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0427
_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)+(0.0512P)²+1.2807P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1188
_reflns_number_gt                1960
_reflns_number_total             2808
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cg101007a_si_002.cif
_cod_data_source_block           (15)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4500132
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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.64791(12) 0.3439(2) 0.02582(8) 0.0434(4) Uani 1 1 d .
C2 C 0.63786(12) 0.17416(19) 0.02631(8) 0.0405(4) Uani 1 1 d .
C3 C 0.60300(12) 0.0878(2) -0.02194(8) 0.0441(4) Uani 1 1 d .
C4 C 0.57574(12) 0.1703(2) -0.07187(8) 0.0455(4) Uani 1 1 d .
C5 C 0.58177(13) 0.3371(2) -0.07546(9) 0.0475(5) Uani 1 1 d .
C6 C 0.61731(12) 0.4178(2) -0.02708(8) 0.0426(4) Uani 1 1 d .
N1 N 0.66391(11) 0.08095(19) 0.07855(7) 0.0500(4) Uani 1 1 d .
N2 N 0.53859(12) 0.0795(2) -0.12292(8) 0.0586(5) Uani 1 1 d .
N3 N 0.62436(14) 0.59603(19) -0.03000(8) 0.0543(4) Uani 1 1 d .
O1 O 0.67995(10) 0.44100(15) 0.06790(6) 0.0614(4) Uani 1 1 d .
O2 O 0.71334(13) 0.14401(18) 0.11703(7) 0.0841(6) Uani 1 1 d .
O3 O 0.63588(11) -0.05652(17) 0.08141(7) 0.0729(5) Uani 1 1 d .
O4 O 0.53914(12) -0.06850(18) -0.12005(7) 0.0777(5) Uani 1 1 d .
O5 O 0.50910(12) 0.15509(19) -0.16567(7) 0.0792(5) Uani 1 1 d .
O6 O 0.5790(12) 0.6724(15) -0.0031(7) 0.086(3) Uani 0.51(4) 1 d P
O7 O 0.6767(12) 0.6547(13) -0.0576(8) 0.112(4) Uani 0.51(4) 1 d P
O6' O 0.5587(10) 0.6766(17) -0.0274(14) 0.114(5) Uani 0.49(4) 1 d P
O7' O 0.6939(8) 0.6473(14) -0.0366(10) 0.111(4) Uani 0.49(4) 1 d P
H5 H 0.5633(12) 0.403(2) -0.1105(8) 0.050(5) Uiso 1 1 d .
H3 H 0.5976(12) -0.021(3) -0.0201(8) 0.053(6) Uiso 1 1 d .
H1 H 0.717(2) 0.407(4) 0.1102(17) 0.159(14) Uiso 1 1 d .
C7 C 0.85940(13) 0.5324(2) 0.23910(9) 0.0511(5) Uani 1 1 d .
C8 C 0.89272(13) 0.6684(2) 0.26680(9) 0.0498(5) Uani 1 1 d .
C9 C 0.86527(13) 0.8167(2) 0.24449(9) 0.0491(5) Uani 1 1 d .
C10 C 0.80586(14) 0.8291(2) 0.19555(10) 0.0549(5) Uani 1 1 d .
C11 C 0.77403(15) 0.6905(3) 0.16904(10) 0.0579(6) Uani 1 1 d .
N4 N 0.80053(11) 0.54395(18) 0.19085(7) 0.0518(4) Uani 1 1 d .
N5 N 0.90066(13) 0.9641(2) 0.27396(9) 0.0659(5) Uani 1 1 d .
O8 O 0.77005(11) 0.40915(18) 0.16634(7) 0.0741(5) Uani 1 1 d .
O9 O 0.95772(14) 0.9475(2) 0.31517(9) 0.0944(6) Uani 1 1 d .
O10 O 0.87169(13) 1.09373(19) 0.25529(9) 0.0912(6) Uani 1 1 d .
H8 H 0.9328(14) 0.659(2) 0.2987(9) 0.057(6) Uiso 1 1 d .
H7 H 0.8750(13) 0.427(3) 0.2500(8) 0.057(6) Uiso 1 1 d .
H11 H 0.7358(15) 0.688(3) 0.1385(10) 0.064(6) Uiso 1 1 d .
H10 H 0.7893(14) 0.927(3) 0.1821(9) 0.067(7) Uiso 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
O1 C1 C6 116.41(16)
O1 C1 C2 129.07(17)
C6 C1 C2 114.51(16)
C3 C2 C1 122.45(17)
C3 C2 N1 116.63(15)
C1 C2 N1 120.92(16)
C4 C3 C2 118.88(17)
C4 C3 H3 121.0(13)
C2 C3 H3 120.1(13)
C3 C4 C5 122.11(18)
C3 C4 N2 119.07(16)
C5 C4 N2 118.83(17)
C6 C5 C4 117.27(18)
C6 C5 H5 117.3(11)
C4 C5 H5 125.4(11)
C5 C6 C1 124.77(17)
C5 C6 N3 118.13(16)
C1 C6 N3 117.10(16)
O2 N1 O3 123.15(17)
O2 N1 C2 118.20(16)
O3 N1 C2 118.64(16)
O5 N2 O4 123.85(18)
O5 N2 C4 118.27(17)
O4 N2 C4 117.89(17)
O7' N3 O6 118.7(9)
O7' N3 O7 26.0(11)
O6 N3 O7 123.6(8)
O7' N3 O6' 125.2(10)
O6 N3 O6' 29.8(10)
O7 N3 O6' 114.7(9)
O7' N3 C6 116.0(7)
O6 N3 C6 117.2(7)
O7 N3 C6 119.2(6)
O6' N3 C6 118.7(8)
C1 O1 H1 127.7(19)
O6' O6 N3 78(2)
O7' O7 N3 75(2)
O6 O6' N3 72(2)
O7 O7' N3 79(2)
N4 C7 C8 120.41(18)
N4 C7 H7 114.4(13)
C8 C7 H7 125.2(13)
C7 C8 C9 118.49(19)
C7 C8 H8 119.2(13)
C9 C8 H8 122.3(13)
C10 C9 C8 121.35(18)
C10 C9 N5 119.65(18)
C8 C9 N5 119.00(18)
C11 C10 C9 118.48(19)
C11 C10 H10 122.3(14)
C9 C10 H10 119.2(14)
N4 C11 C10 120.5(2)
N4 C11 H11 115.5(15)
C10 C11 H11 124.0(15)
O8 N4 C7 117.75(15)
O8 N4 C11 121.51(17)
C7 N4 C11 120.74(17)
O10 N5 O9 124.80(19)
O10 N5 C9 117.81(19)
O9 N5 C9 117.38(18)
N4 O8 H1 122.1(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.314(2)
C1 C6 1.405(3)
C1 C2 1.410(2)
C2 C3 1.383(3)
C2 N1 1.456(2)
C3 C4 1.370(3)
C3 H3 0.90(2)
C4 C5 1.383(2)
C4 N2 1.461(2)
C5 C6 1.365(3)
C5 H5 0.994(19)
C6 N3 1.477(2)
N1 O2 1.214(2)
N1 O3 1.217(2)
N2 O5 1.215(2)
N2 O4 1.224(2)
N3 O7' 1.168(10)
N3 O6 1.176(11)
N3 O7 1.191(10)
N3 O6' 1.208(13)
O1 H1 1.11(4)
O6 O6' 0.61(2)
O7 O7' 0.53(2)
C7 N4 1.352(2)
C7 C8 1.361(3)
C7 H7 0.93(2)
C8 C9 1.374(3)
C8 H8 0.91(2)
C9 C10 1.369(3)
C9 N5 1.467(2)
C10 C11 1.360(3)
C10 H10 0.90(2)
C11 N4 1.354(2)
C11 H11 0.86(2)
N4 O8 1.309(2)
N5 O10 1.217(2)
N5 O9 1.220(2)
O8 H1 1.45(4)
