#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/18/2231855.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2231855
loop_
_publ_author_name
'Paixão, Drielly A.'
'Guilardi, Silvana'
'Fátima, Ângelo de'
'Araujo, Débora P.'
'Oliveira, Francinely C.'
_publ_section_title
;
 N-(2-Nitrooxyethyl)picolinamide
;
_journal_coeditor_code           CV5154
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2816
_journal_paper_doi               10.1107/S1600536811039572
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C8 H9 N3 O4'
_chemical_formula_moiety         'C8 H9 N3 O4'
_chemical_formula_sum            'C8 H9 N3 O4'
_chemical_formula_weight         211.18
_chemical_name_common
;
N-(2-Nitrooxyethyl)picolinamide
;
_chemical_name_systematic
;
N-(2-Nitrooxyethyl)pyridine-2-carboxamide
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.5075(2)
_cell_length_b                   13.6114(5)
_cell_length_c                   12.6822(4)
_cell_measurement_reflns_used    2165
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.91
_cell_volume                     950.72(6)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4037
_diffrn_reflns_reduction_process
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.21
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.486
_exptl_crystal_size_mid          0.207
_exptl_crystal_size_min          0.191
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.152
_refine_ls_extinction_coef       0.124(13)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1265
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.038
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0654P)²+0.0645P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1079
_reflns_number_gt                1039
_reflns_number_total             1265
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cv5154.cif
_cod_data_source_block           I
_cod_database_code               2231855
_cod_database_fobs_code          2231855
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 -0.1820(3) 0.49141(13) 0.05722(14) 0.0662(5) Uani d . 1
O O2 0.2098(3) 0.55263(11) -0.11459(12) 0.0528(4) Uani d . 1
O O3 -0.0499(4) 0.67762(12) -0.11167(15) 0.0705(5) Uani d . 1
O O4 -0.1235(4) 0.54631(16) -0.20249(14) 0.0797(6) Uani d . 1
N N1 0.1892(3) 0.31135(13) 0.17680(14) 0.0509(5) Uani d . 1
N N2 0.2136(4) 0.49676(13) 0.10379(15) 0.0532(5) Uani d . 1
H H 0.3331 0.4648 0.1308 0.064 Uiso calc R 1
N N3 -0.0061(4) 0.59684(13) -0.14445(15) 0.0532(5) Uani d . 1
C C1 -0.0042(4) 0.34497(13) 0.12528(15) 0.0430(5) Uani d . 1
C C2 0.1867(5) 0.21623(15) 0.20374(19) 0.0570(6) Uani d . 1
H H2 0.3191 0.1914 0.2407 0.068 Uiso calc R 1
C C3 -0.0002(5) 0.15319(15) 0.17994(18) 0.0565(6) Uani d . 1
H H3 0.0066 0.0875 0.1998 0.068 Uiso calc R 1
C C4 -0.1974(5) 0.18928(16) 0.12612(19) 0.0561(6) Uani d . 1
H H4 -0.3265 0.1484 0.1086 0.067 Uiso calc R 1
C C5 -0.2003(4) 0.28722(15) 0.09855(18) 0.0516(5) Uani d . 1
H H5 -0.332 0.3138 0.0626 0.062 Uiso calc R 1
C C6 -0.0002(4) 0.45146(14) 0.09262(15) 0.0459(5) Uani d . 1
C C7 0.2509(5) 0.59775(15) 0.07192(18) 0.0592(6) Uani d . 1
H H7A 0.3618 0.629 0.1209 0.071 Uiso calc R 1
H H7B 0.0973 0.6325 0.0754 0.071 Uiso calc R 1
C C8 0.3520(5) 0.60631(17) -0.03806(19) 0.0595(6) Uani d . 1
H H8A 0.3569 0.6751 -0.0581 0.071 Uiso calc R 1
H H8B 0.5171 0.5816 -0.0387 0.071 Uiso calc R 1
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 0 '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 0.006 '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
N3 O2 C8 115.41(16)
C1 N1 C2 116.73(19)
C6 N2 C7 122.2(2)
C6 N2 H 118.9
C7 N2 H 118.9
O4 N3 O3 129.1(2)
O4 N3 O2 112.47(19)
O3 N3 O2 118.4(2)
N1 C1 C5 123.50(19)
N1 C1 C6 116.99(18)
C5 C1 C6 119.49(19)
N1 C2 C3 123.7(2)
N1 C2 H2 118.1
C3 C2 H2 118.1
C4 C3 C2 118.6(2)
C4 C3 H3 120.7
C2 C3 H3 120.7
C3 C4 C5 118.8(2)
C3 C4 H4 120.6
C5 C4 H4 120.6
C4 C5 C1 118.7(2)
C4 C5 H5 120.7
C1 C5 H5 120.7
O1 C6 N2 123.66(18)
O1 C6 C1 121.03(18)
N2 C6 C1 115.30(18)
N2 C7 C8 112.60(19)
N2 C7 H7A 109.1
C8 C7 H7A 109.1
N2 C7 H7B 109.1
C8 C7 H7B 109.1
H7A C7 H7B 107.8
O2 C8 C7 112.49(19)
O2 C8 H8A 109.1
C7 C8 H8A 109.1
O2 C8 H8B 109.1
C7 C8 H8B 109.1
H8A C8 H8B 107.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C6 1.225(3)
O2 N3 1.385(3)
O2 C8 1.445(3)
O3 N3 1.200(2)
O4 N3 1.197(3)
N1 C1 1.330(3)
N1 C2 1.339(3)
N2 C6 1.337(3)
N2 C7 1.447(3)
N2 H 0.86
C1 C5 1.378(3)
C1 C6 1.508(3)
C2 C3 1.374(3)
C2 H2 0.93
C3 C4 1.374(4)
C3 H3 0.93
C4 C5 1.378(3)
C4 H4 0.93
C5 H5 0.93
C7 C8 1.506(3)
C7 H7A 0.97
C7 H7B 0.97
C8 H8A 0.97
C8 H8B 0.97
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H N1 1 0.86 2.31 2.692(3) 107.2
C8 H8B O1 1_655 0.97 2.39 3.239(3) 145.4
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
C8 O2 N3 O4 -175.41(19)
C8 O2 N3 O3 5.3(3)
C2 N1 C1 C5 -0.5(3)
C2 N1 C1 C6 -178.70(19)
C1 N1 C2 C3 0.9(3)
N1 C2 C3 C4 -0.5(4)
C2 C3 C4 C5 -0.3(3)
C3 C4 C5 C1 0.6(3)
N1 C1 C5 C4 -0.2(3)
C6 C1 C5 C4 177.95(19)
C7 N2 C6 O1 -1.7(3)
C7 N2 C6 C1 177.33(19)
N1 C1 C6 O1 -170.5(2)
C5 C1 C6 O1 11.2(3)
N1 C1 C6 N2 10.4(3)
C5 C1 C6 N2 -167.8(2)
C6 N2 C7 C8 -94.3(3)
N3 O2 C8 C7 76.5(2)
N2 C7 C8 O2 52.7(3)
