#------------------------------------------------------------------------------
#$Date: 2019-11-22 19:33:15 +0200 (Fri, 22 Nov 2019) $
#$Revision: 231343 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/64/4516492.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_4516492
loop_
_publ_author_name
'Rybarczyk-Pirek, Agnieszka J.'
'Łukomska-Rogala, Marlena'
'Wojtulewski, Sławomir'
'Palusiak, Marcin'
_publ_section_title
;
 N-Oxide as a Proton Accepting Group in Multicomponent Crystals: X-ray and
 Theoretical Studies on New p-Nitropyridine-N-oxide Co-Crystals
;
_journal_issue                   12
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5802
_journal_paper_doi               10.1021/acs.cgd.5b01177
_journal_volume                  15
_journal_year                    2015
_chemical_formula_sum            'C12 H10 N2 O8'
_chemical_formula_weight         310.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 108.299(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0878(3)
_cell_length_b                   6.82420(10)
_cell_length_c                   15.8918(3)
_cell_measurement_temperature    100(2)
_cell_volume                     1244.62(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS (Sheldrich, 1986)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4052
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'SuperNova, Dual, Mo at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7764
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.495
_diffrn_reflns_theta_min         3.276
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71629
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.348
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.059
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         2312
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0389
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0327P)²+1.1495P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.0936
_reflns_number_gt                2159
_reflns_number_total             2312
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5b01177_si_002.cif
_cod_data_source_block           compound2
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4516492
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O13 O 0.45143(10) 0.66634(18) 0.69754(7) 0.0164(3) Uani 1 1 d . .
C13 C 0.40011(13) 0.7791(2) 0.62445(10) 0.0136(3) Uani 1 1 d . .
C12 C 0.44419(14) 0.9575(2) 0.60852(10) 0.0136(3) Uani 1 1 d . .
H12 H 0.5152 1.0060 0.6481 0.016 Uiso 1 1 calc R U
O14 O 0.24636(10) 0.53537(18) 0.57940(8) 0.0171(3) Uani 1 1 d . .
C11 C 0.38323(14) 1.0658(2) 0.53372(10) 0.0139(3) Uani 1 1 d . .
C10 C 0.43192(14) 1.2570(2) 0.52002(10) 0.0141(3) Uani 1 1 d . .
C15 C 0.23859(14) 0.8129(3) 0.48982(10) 0.0150(3) Uani 1 1 d . .
C16 C 0.28046(14) 0.9944(2) 0.47372(10) 0.0146(3) Uani 1 1 d . .
H16 H 0.2398 1.0684 0.4228 0.018 Uiso 1 1 calc R U
O10 O 0.52354(10) 1.32112(18) 0.57161(7) 0.0174(3) Uani 1 1 d . .
O11 O 0.37052(10) 1.35370(18) 0.44867(7) 0.0178(3) Uani 1 1 d . .
O15 O 0.13784(10) 0.7430(2) 0.43066(8) 0.0203(3) Uani 1 1 d . .
C14 C 0.29597(14) 0.7061(2) 0.56589(10) 0.0138(3) Uani 1 1 d . .
H15 H 0.133(2) 0.626(4) 0.4391(15) 0.035(7) Uiso 1 1 d . .
H14 H 0.290(2) 0.470(4) 0.6317(17) 0.050(7) Uiso 1 1 d . .
H13 H 0.524(2) 0.719(4) 0.7306(17) 0.050(7) Uiso 1 1 d . .
H11 H 0.409(2) 1.467(4) 0.4445(16) 0.048(7) Uiso 1 1 d . .
O1 O 0.67152(10) 0.78196(17) 0.78513(7) 0.0174(3) Uani 1 1 d . .
N1 N 0.74229(11) 0.6313(2) 0.79464(9) 0.0141(3) Uani 1 1 d . .
C6 C 0.84909(14) 0.6364(3) 0.85716(11) 0.0183(4) Uani 1 1 d . .
H6 H 0.8728 0.7494 0.8933 0.022 Uiso 1 1 calc R U
C4 C 0.88679(15) 0.3178(3) 0.81427(11) 0.0187(4) Uani 1 1 d . .
C2 C 0.70717(14) 0.4713(3) 0.74224(10) 0.0165(4) Uani 1 1 d . .
H2 H 0.6318 0.4698 0.6995 0.020 Uiso 1 1 calc R U
C5 C 0.92267(15) 0.4789(3) 0.86810(12) 0.0220(4) Uani 1 1 d . .
H5 H 0.9971 0.4809 0.9120 0.026 Uiso 1 1 calc R U
C3 C 0.77883(15) 0.3118(3) 0.75012(11) 0.0178(4) Uani 1 1 d . .
H3 H 0.7550 0.2008 0.7127 0.021 Uiso 1 1 calc R U
O42 O 1.05305(13) 0.1501(2) 0.89194(13) 0.0549(5) Uani 1 1 d . .
O41 O 0.93329(12) 0.0082(2) 0.77623(9) 0.0302(3) Uani 1 1 d . .
N4 N 0.96317(13) 0.1469(2) 0.82765(12) 0.0281(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
O13 C13 C12 123.49(14)
O13 C13 C14 115.92(14)
C12 C13 C14 120.57(15)
C13 C12 C11 119.37(15)
C16 C11 C12 121.03(15)
C16 C11 C10 121.25(15)
C12 C11 C10 117.71(14)
O10 C10 O11 122.62(15)
O10 C10 C11 122.16(15)
O11 C10 C11 115.22(14)
O15 C15 C16 118.69(14)
O15 C15 C14 120.38(15)
C16 C15 C14 120.90(15)
C15 C16 C11 118.83(15)
O14 C14 C15 117.46(14)
O14 C14 C13 123.32(14)
C15 C14 C13 119.22(15)
O1 N1 C2 119.42(13)
O1 N1 C6 119.85(14)
C2 N1 C6 120.73(14)
N1 C6 C5 120.11(16)
C5 C4 C3 121.51(16)
C5 C4 N4 119.05(16)
C3 C4 N4 119.40(16)
N1 C2 C3 121.01(15)
C6 C5 C4 118.82(16)
C2 C3 C4 117.81(16)
O41 N4 O42 124.23(16)
O41 N4 C4 118.54(15)
O42 N4 C4 117.21(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O13 C13 1.3688(19)
C13 C12 1.384(2)
C13 C14 1.401(2)
C12 C11 1.397(2)
O14 C14 1.358(2)
C11 C16 1.395(2)
C11 C10 1.475(2)
C10 O10 1.233(2)
C10 O11 1.320(2)
C15 O15 1.370(2)
C15 C16 1.392(2)
C15 C14 1.395(2)
O1 N1 1.3154(18)
N1 C2 1.358(2)
N1 C6 1.360(2)
C6 C5 1.371(3)
C4 C5 1.377(3)
C4 C3 1.382(2)
C4 N4 1.461(2)
C2 C3 1.372(2)
O42 N4 1.236(2)
O41 N4 1.228(2)
