#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/79/2017927.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_2017927
loop_
_publ_author_name
'Tutughamiarso, Maya'
'Bolte, Michael'
'Wagner, Guido'
'Egert, Ernst'
_publ_section_title
;
 Five pseudopolymorphs and a cocrystal of nitrofurantoin
;
_journal_coeditor_code           EG3064
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o18
_journal_page_last               o25
_journal_paper_doi               10.1107/S0108270110046755
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C9 H11 N3 O2, C3 H7 N O'
_chemical_formula_moiety         'C9 H11 N3 O2, C3 H7 N O'
_chemical_formula_sum            'C12 H18 N4 O3'
_chemical_formula_weight         266.30
_chemical_name_systematic
;
2,6-diacetaminopyridine dimethylformamide monosolvate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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                 94.327(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.3031(7)
_cell_length_b                   13.1539(8)
_cell_length_c                   9.3959(5)
_cell_measurement_reflns_used    6874
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.9
_cell_measurement_theta_min      3.31
_cell_volume                     1393.00(14)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2001)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2001)'
_computing_data_reduction        'X-AREA (Stoe & Cie, 2001)'
_computing_molecular_graphics
;
Mercury (Macrae et al., 2008) and XP (Sheldrick, 2008);
;
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Stoe IPDS II two-circle diffractometer'
_diffrn_measurement_method       ω
_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  0.1003
_diffrn_reflns_av_sigmaI/netI    0.0595
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12406
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.64
_diffrn_reflns_theta_min         3.31
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.185
_refine_ls_extinction_coef       0.024(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.927
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2603
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.927
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0415
_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)+(0.0587P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.0990
_reflns_number_gt                1967
_reflns_number_total             2603
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            eg3064.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2017927
_cod_database_fobs_code          2017927
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_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
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.81887(10) 0.42930(9) 0.33685(12) 0.0280(3) Uani d . 1 . .
C C2 0.77593(12) 0.52246(11) 0.30726(16) 0.0299(3) Uani d . 1 . .
C C3 0.77636(13) 0.59988(11) 0.40791(17) 0.0356(4) Uani d . 1 . .
H H3 0.7454 0.6653 0.3838 0.043 Uiso calc R 1 . .
C C4 0.82346(14) 0.57795(12) 0.54412(17) 0.0372(4) Uani d . 1 . .
H H4 0.8245 0.6291 0.6156 0.045 Uiso calc R 1 . .
C C5 0.86915(13) 0.48275(12) 0.57834(16) 0.0340(4) Uani d . 1 . .
H H5 0.9016 0.4672 0.6720 0.041 Uiso calc R 1 . .
C C6 0.86552(12) 0.41064(11) 0.46952(15) 0.0278(3) Uani d . 1 . .
N N21 0.72814(12) 0.53106(10) 0.16546(14) 0.0347(3) Uani d . 1 . .
H H21 0.7197(16) 0.4710(17) 0.118(2) 0.053(5) Uiso d . 1 . .
C C22 0.69884(14) 0.61764(12) 0.09140(18) 0.0371(4) Uani d . 1 . .
C C23 0.64755(17) 0.59993(13) -0.05894(19) 0.0469(4) Uani d . 1 . .
H H23A 0.5641 0.6209 -0.0674 0.070 Uiso calc PR 0.42(5) A 1
H H23B 0.6532 0.5276 -0.0822 0.070 Uiso calc PR 0.42(5) A 1
H H23C 0.6919 0.6398 -0.1251 0.070 Uiso calc PR 0.42(5) A 1
H H23D 0.5674 0.5718 -0.0572 0.070 Uiso d PR 0.58(5) A 2
H H23E 0.6978 0.5519 -0.1067 0.070 Uiso d PR 0.58(5) A 2
H H23F 0.6440 0.6646 -0.1111 0.070 Uiso d PR 0.58(5) A 2
O O24 0.71192(12) 0.70272(9) 0.14172(14) 0.0516(3) Uani d . 1 . .
N N61 0.91380(11) 0.31284(10) 0.48319(13) 0.0285(3) Uani d . 1 . .
H H61 0.9215(15) 0.2810(14) 0.404(2) 0.042(5) Uiso d . 1 . .
C C62 0.95180(12) 0.26280(12) 0.60424(15) 0.0310(3) Uani d . 1 . .
C C63 1.00524(16) 0.16042(13) 0.58083(17) 0.0428(4) Uani d . 1 . .
H H63A 1.0861 0.1584 0.6265 0.064 Uiso calc PR 0.66(2) B 1
H H63B 1.0075 0.1481 0.4782 0.064 Uiso calc PR 0.66(2) B 1
H H63C 0.9571 0.1078 0.6225 0.064 Uiso calc PR 0.66(2) B 1
H H63D 0.9488 0.1187 0.5220 0.064 Uiso d PR 0.34(2) B 2
H H63E 1.0236 0.1270 0.6731 0.064 Uiso d PR 0.34(2) B 2
H H63F 1.0783 0.1686 0.5320 0.064 Uiso d PR 0.34(2) B 2
O O64 0.94306(11) 0.29781(8) 0.72423(11) 0.0419(3) Uani d . 1 . .
O O1A 0.66772(10) 0.34158(9) 0.02033(13) 0.0424(3) Uani d . 1 . .
C C2A 0.65996(13) 0.26859(12) 0.10092(17) 0.0345(4) Uani d . 1 . .
H H2A 0.7024 0.2723 0.1920 0.041 Uiso calc R 1 . .
N N3A 0.59688(11) 0.18486(10) 0.07072(14) 0.0342(3) Uani d . 1 . .
C C4A 0.59146(16) 0.10297(13) 0.1735(2) 0.0453(4) Uani d . 1 . .
H H4A1 0.6417 0.1197 0.2599 0.068 Uiso calc R 1 . .
H H4A2 0.6196 0.0399 0.1321 0.068 Uiso calc R 1 . .
H H4A3 0.5093 0.0940 0.1980 0.068 Uiso calc R 1 . .
C C5A 0.53209(15) 0.17015(14) -0.06731(19) 0.0428(4) Uani d . 1 . .
H H5A1 0.5349 0.2328 -0.1234 0.064 Uiso calc R 1 . .
H H5A2 0.4493 0.1532 -0.0534 0.064 Uiso calc R 1 . .
H H5A3 0.5684 0.1146 -0.1182 0.064 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 0.0000 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 N1 C2 . . 118.16(12) ?
N1 C2 C3 . . 123.14(14) ?
N1 C2 N21 . . 112.22(13) ?
C3 C2 N21 . . 124.62(14) ?
C4 C3 C2 . . 117.36(14) ?
C4 C3 H3 . . 121.3 ?
C2 C3 H3 . . 121.3 ?
C3 C4 C5 . . 121.09(14) ?
C3 C4 H4 . . 119.5 ?
C5 C4 H4 . . 119.5 ?
C4 C5 C6 . . 117.13(14) ?
C4 C5 H5 . . 121.4 ?
C6 C5 H5 . . 121.4 ?
N1 C6 C5 . . 123.11(14) ?
N1 C6 N61 . . 112.17(12) ?
C5 C6 N61 . . 124.67(13) ?
C22 N21 C2 . . 127.83(14) ?
C22 N21 H21 . . 117.5(13) ?
C2 N21 H21 . . 114.6(13) ?
O24 C22 N21 . . 123.46(16) ?
O24 C22 C23 . . 122.22(15) ?
N21 C22 C23 . . 114.32(14) ?
C22 C23 H23A . . 109.5 ?
C22 C23 H23B . . 109.5 ?
C22 C23 H23C . . 109.5 ?
C22 C23 H23D . . 109.5 ?
C22 C23 H23E . . 109.5 ?
H23D C23 H23E . . 109.4 ?
C22 C23 H23F . . 109.5 ?
H23D C23 H23F . . 109.4 ?
H23E C23 H23F . . 109.4 ?
C62 N61 C6 . . 128.32(13) ?
C62 N61 H61 . . 116.3(12) ?
C6 N61 H61 . . 115.3(12) ?
O64 C62 N61 . . 123.06(14) ?
O64 C62 C63 . . 122.18(13) ?
N61 C62 C63 . . 114.76(13) ?
C62 C63 H63A . . 109.5 ?
C62 C63 H63B . . 109.5 ?
C62 C63 H63C . . 109.5 ?
C62 C63 H63D . . 109.5 ?
C62 C63 H63E . . 109.5 ?
H63D C63 H63E . . 109.5 ?
C62 C63 H63F . . 109.5 ?
H63D C63 H63F . . 109.5 ?
H63E C63 H63F . . 109.5 ?
O1A C2A N3A . . 125.21(15) ?
O1A C2A H2A . . 117.4 ?
N3A C2A H2A . . 117.4 ?
C2A N3A C4A . . 121.41(14) ?
C2A N3A C5A . . 121.75(14) ?
C4A N3A C5A . . 116.83(14) ?
N3A C4A H4A1 . . 109.5 ?
N3A C4A H4A2 . . 109.5 ?
H4A1 C4A H4A2 . . 109.5 ?
N3A C4A H4A3 . . 109.5 ?
H4A1 C4A H4A3 . . 109.5 ?
H4A2 C4A H4A3 . . 109.5 ?
N3A C5A H5A1 . . 109.5 ?
N3A C5A H5A2 . . 109.5 ?
H5A1 C5A H5A2 . . 109.5 ?
N3A C5A H5A3 . . 109.5 ?
H5A1 C5A H5A3 . . 109.5 ?
H5A2 C5A H5A3 . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C6 . 1.3390(19) ?
N1 C2 . 1.3395(19) ?
C2 C3 . 1.389(2) ?
C2 N21 . 1.404(2) ?
C3 C4 . 1.379(2) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.383(2) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.393(2) ?
C5 H5 . 0.9500 ?
C6 N61 . 1.3995(19) ?
N21 C22 . 1.362(2) ?
N21 H21 . 0.91(2) ?
C22 O24 . 1.220(2) ?
C22 C23 . 1.504(2) ?
C23 H23A . 0.9800 ?
C23 H23B . 0.9800 ?
C23 H23C . 0.9800 ?
C23 H23D . 0.9804 ?
C23 H23E . 0.9804 ?
C23 H23F . 0.9805 ?
N61 C62 . 1.3556(19) ?
N61 H61 . 0.87(2) ?
C62 O64 . 1.2287(18) ?
C62 C63 . 1.499(2) ?
C63 H63A . 0.9800 ?
C63 H63B . 0.9800 ?
C63 H63C . 0.9800 ?
C63 H63D . 0.9801 ?
C63 H63E . 0.9801 ?
C63 H63F . 0.9801 ?
O1A C2A . 1.2300(19) ?
C2A N3A . 1.331(2) ?
C2A H2A . 0.9500 ?
N3A C4A . 1.451(2) ?
N3A C5A . 1.453(2) ?
C4A H4A1 . 0.9800 ?
C4A H4A2 . 0.9800 ?
C4A H4A3 . 0.9800 ?
C5A H5A1 . 0.9800 ?
C5A H5A2 . 0.9800 ?
C5A H5A3 . 0.9800 ?
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
N21 H21 O1A . 0.91(2) 2.00(2) 2.8979(18) 168.8(17)
N61 H61 O64 4_565 0.87(2) 2.01(2) 2.8757(16) 177.4(18)
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 N1 C2 C3 . . . . -0.8(2) ?
C6 N1 C2 N21 . . . . -179.05(12) ?
N1 C2 C3 C4 . . . . -0.1(2) ?
N21 C2 C3 C4 . . . . 177.94(14) ?
C2 C3 C4 C5 . . . . 0.5(2) ?
C3 C4 C5 C6 . . . . 0.1(2) ?
C2 N1 C6 C5 . . . . 1.4(2) ?
C2 N1 C6 N61 . . . . -176.13(11) ?
C4 C5 C6 N1 . . . . -1.0(2) ?
C4 C5 C6 N61 . . . . 176.14(13) ?
N1 C2 N21 C22 . . . . -165.90(14) ?
C3 C2 N21 C22 . . . . 15.8(2) ?
C2 N21 C22 O24 . . . . 0.5(3) ?
C2 N21 C22 C23 . . . . -179.08(14) ?
N1 C6 N61 C62 . . . . -169.19(13) ?
C5 C6 N61 C62 . . . . 13.4(2) ?
C6 N61 C62 O64 . . . . 3.5(2) ?
C6 N61 C62 C63 . . . . -176.79(13) ?
O1A C2A N3A C4A . . . . -179.06(14) ?
O1A C2A N3A C5A . . . . 2.1(2) ?
