#------------------------------------------------------------------------------
#$Date: 2019-11-22 19:33:15 +0200 (Fri, 22 Nov 2019) $
#$Revision: 231343 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/64/4516491.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_4516491
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 O6'
_chemical_formula_weight         278.22
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.2042(2)
_cell_length_b                   13.5361(3)
_cell_length_c                   14.7000(3)
_cell_measurement_temperature    100(2)
_cell_volume                     2428.40(8)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0186
_diffrn_reflns_av_sigmaI/netI    0.0146
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8164
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.77
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72241
_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            colorless
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.512
_exptl_crystal_size_mid          0.361
_exptl_crystal_size_min          0.186
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         2258
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0318
_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)+(0.0418P)²+1.2369P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.0932
_reflns_number_gt                2080
_reflns_number_total             2258
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5b01177_si_002.cif
_cod_data_source_block           compound1
_cod_original_sg_symbol_H-M      'P bca'
_cod_database_code               4516491
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
H11 H 0.7726(19) 0.1656(17) 0.6296(17) 0.060(7) Uiso 1 1 d .
H12 H 0.9649(19) 0.0901(17) 0.8356(17) 0.056(7) Uiso 1 1 d .
O11 O 0.74207(8) 0.14178(8) 0.68639(7) 0.0215(2) Uani 1 1 d .
C11 C 0.77596(11) 0.08675(9) 0.83575(9) 0.0159(3) Uani 1 1 d .
O10 O 0.91653(8) 0.12620(9) 0.72955(7) 0.0271(3) Uani 1 1 d .
O12 O 0.96017(8) 0.07161(8) 0.89469(8) 0.0265(3) Uani 1 1 d .
C16 C 0.66338(12) 0.07935(10) 0.85236(10) 0.0196(3) Uani 1 1 d .
H16 H 0.6129 0.0920 0.8046 0.024 Uiso 1 1 calc R
C12 C 0.85000(12) 0.06639(10) 0.90663(10) 0.0189(3) Uani 1 1 d .
C10 C 0.81776(11) 0.11924(10) 0.74611(10) 0.0176(3) Uani 1 1 d .
C13 C 0.81076(13) 0.04081(10) 0.99267(10) 0.0221(3) Uani 1 1 d .
H13 H 0.8605 0.0271 1.0407 0.027 Uiso 1 1 calc R
C15 C 0.62486(13) 0.05384(11) 0.93735(10) 0.0241(3) Uani 1 1 d .
H15 H 0.5483 0.0488 0.9481 0.029 Uiso 1 1 calc R
C14 C 0.69921(13) 0.03549(11) 1.00753(10) 0.0244(3) Uani 1 1 d .
H14 H 0.6727 0.0191 1.0664 0.029 Uiso 1 1 calc R
N1 N 0.73550(9) 0.19846(8) 0.47288(7) 0.0153(3) Uani 1 1 d .
O1 O 0.81095(8) 0.21025(8) 0.53602(6) 0.0208(2) Uani 1 1 d .
N4 N 0.49987(10) 0.15353(9) 0.27108(8) 0.0204(3) Uani 1 1 d .
C4 C 0.58230(11) 0.17016(10) 0.34181(9) 0.0160(3) Uani 1 1 d .
C5 C 0.69207(11) 0.16155(10) 0.31945(9) 0.0160(3) Uani 1 1 d .
H5 H 0.7142 0.1464 0.2591 0.019 Uiso 1 1 calc R
C3 C 0.54831(11) 0.19344(10) 0.42895(9) 0.0172(3) Uani 1 1 d .
H3 H 0.4727 0.1991 0.4434 0.021 Uiso 1 1 calc R
C2 C 0.62763(11) 0.20816(10) 0.49407(9) 0.0175(3) Uani 1 1 d .
H2 H 0.6068 0.2252 0.5543 0.021 Uiso 1 1 calc R
O41 O 0.40519(8) 0.13960(9) 0.29528(7) 0.0282(3) Uani 1 1 d .
C6 C 0.76813(11) 0.17551(10) 0.38717(9) 0.0163(3) Uani 1 1 d .
H6 H 0.8440 0.1691 0.3739 0.020 Uiso 1 1 calc R
O42 O 0.53042(9) 0.15420(9) 0.19107(7) 0.0306(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 0.0033 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
C16 C11 C12 119.19(13)
C16 C11 C10 121.01(12)
C12 C11 C10 119.76(12)
C15 C16 C11 120.72(13)
O12 C12 C13 118.01(13)
O12 C12 C11 122.02(13)
C13 C12 C11 119.96(13)
O10 C10 O11 122.62(13)
O10 C10 C11 122.37(13)
O11 C10 C11 115.01(12)
C14 C13 C12 119.63(13)
C16 C15 C14 119.50(14)
C13 C14 C15 120.98(14)
O1 N1 C6 118.48(11)
O1 N1 C2 120.26(11)
C6 N1 C2 121.26(12)
O41 N4 O42 124.30(12)
O41 N4 C4 117.78(11)
O42 N4 C4 117.92(12)
C3 C4 C5 121.96(12)
C3 C4 N4 119.13(12)
C5 C4 N4 118.90(12)
C6 C5 C4 118.04(12)
C2 C3 C4 117.80(13)
N1 C2 C3 120.54(12)
N1 C6 C5 120.39(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O11 C10 1.3104(17)
C11 C16 1.399(2)
C11 C12 1.4064(19)
C11 C10 1.4799(19)
O10 C10 1.2334(17)
O12 C12 1.3578(18)
C16 C15 1.379(2)
C12 C13 1.396(2)
C13 C14 1.381(2)
C15 C14 1.396(2)
N1 O1 1.3171(14)
N1 C6 1.3573(17)
N1 C2 1.3592(17)
N4 O41 1.2236(16)
N4 O42 1.2338(16)
N4 C4 1.4641(17)
C4 C3 1.3829(19)
C4 C5 1.3844(19)
C5 C6 1.3741(19)
C3 C2 1.3758(19)
