#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/04/7150481.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_7150481
loop_
_publ_author_name
'Crampton, Michael R.'
'Emokpae, Thomas A.'
'Howard, Judith A. K.'
'Isanbor, Chukwuemeka'
'Mondal, Raju'
_publ_section_title
;
 Kinetic and equilibrium studies of σ-adduct formation and
 nucleophilic substitution in the reactions of
 2-phenoxy-3,5-dinitropyridine and 2-ethoxy-3,5-dinitropyridine with
 aliphatic amines in dipolar aprotic solventsElectronic supplementary
 information (ESI) available: Tables 10--15. See
 http://www.rsc.org/suppdata/ob/b2/b211639c/
;
_journal_issue                   6
_journal_name_full               'Organic &  Biomolecular Chemistry'
_journal_page_first              1004
_journal_paper_doi               10.1039/b211639c
_journal_volume                  1
_journal_year                    2003
_chemical_formula_sum            'C10 H12 N4 O4'
_chemical_formula_weight         252.24
_chemical_name_common            NPIP
_chemical_name_systematic
; 
2-Piperidine-3,5-dinitropyridine 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                94.29(3)
_cell_angle_beta                 95.28(3)
_cell_angle_gamma                91.80(3)
_cell_formula_units_Z            2
_cell_length_a                   5.9847(12)
_cell_length_b                   7.3833(15)
_cell_length_c                   12.375(3)
_cell_measurement_reflns_used    2836
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.4825
_cell_measurement_theta_min      3.1145
_cell_volume                     542.6(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'smart 6k CCD area detector'
_diffrn_measurement_method       'omega 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  0.0166
_diffrn_reflns_av_sigmaI/netI    0.0204
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4225
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.66
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.776709
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS v.2.03 (Bruker, 2001), R(int) = 0.0301 before correction'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       Cube
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2484
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0332
_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)+(0.0557P)²+0.1288P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.0963
_reflns_number_gt                2245
_reflns_number_total             2484
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b211639c.txt
_cod_data_source_block           sad
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_refine_ls_hydrogen_treatment' value 'Refall' changed to
'refall' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        542.53(19)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7150481
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O 0.22320(14) 0.13842(12) 0.00238(7) 0.0268(2) Uani 1 1 d . . .
O2 O 0.14441(14) 0.26952(12) -0.37638(7) 0.0264(2) Uani 1 1 d . . .
O3 O -0.02275(14) 0.24227(12) 0.10767(6) 0.0254(2) Uani 1 1 d . . .
O1 O -0.19528(14) 0.31833(11) -0.44237(6) 0.0239(2) Uani 1 1 d . . .
N3 N 0.05032(15) 0.21926(12) 0.01795(7) 0.0191(2) Uani 1 1 d . . .
N2 N -0.04787(15) 0.31769(12) -0.36594(7) 0.0183(2) Uani 1 1 d . . .
N4 N -0.38724(14) 0.59464(12) -0.29710(7) 0.0168(2) Uani 1 1 d . . .
N1 N -0.39735(15) 0.44419(12) -0.14077(7) 0.0190(2) Uani 1 1 d . . .
C4 C -0.07251(17) 0.29405(14) -0.07314(8) 0.0172(2) Uani 1 1 d . . .
C5 C -0.28706(18) 0.36070(14) -0.06326(9) 0.0187(2) Uani 1 1 d . . .
C6 C -0.61065(17) 0.66767(15) -0.28308(9) 0.0181(2) Uani 1 1 d . . .
C3 C 0.01294(17) 0.28740(14) -0.17342(9) 0.0168(2) Uani 1 1 d . . .
C2 C -0.10750(17) 0.36631(13) -0.25637(8) 0.0159(2) Uani 1 1 d . . .
C10 C -0.26700(18) 0.68067(14) -0.37947(9) 0.0185(2) Uani 1 1 d . . .
C1 C -0.30020(17) 0.47030(13) -0.23458(8) 0.0158(2) Uani 1 1 d . . .
C9 C -0.25344(18) 0.88743(14) -0.35607(9) 0.0197(2) Uani 1 1 d . . .
C8 C -0.48353(18) 0.96536(15) -0.34429(10) 0.0214(2) Uani 1 1 d . . .
C7 C -0.59535(18) 0.87264(15) -0.25617(9) 0.0211(2) Uani 1 1 d . . .
H10A H -0.115(2) 0.6374(19) -0.3778(11) 0.023(3) Uiso 1 1 d . . .
H3 H 0.144(2) 0.226(2) -0.1851(11) 0.024(3) Uiso 1 1 d . . .
H8A H -0.579(2) 0.942(2) -0.4137(12) 0.025(3) Uiso 1 1 d . . .
H6A H -0.677(2) 0.6002(19) -0.2284(12) 0.024(3) Uiso 1 1 d . . .
H10B H -0.347(2) 0.642(2) -0.4534(12) 0.025(3) Uiso 1 1 d . . .
H6B H -0.703(2) 0.6404(19) -0.3533(12) 0.021(3) Uiso 1 1 d . . .
H7A H -0.749(2) 0.9141(19) -0.2501(12) 0.025(3) Uiso 1 1 d . . .
H7B H -0.511(2) 0.9044(19) -0.1834(12) 0.022(3) Uiso 1 1 d . . .
H5 H -0.360(2) 0.3440(19) 0.0015(12) 0.025(4) Uiso 1 1 d . . .
H9A H -0.157(2) 0.9213(19) -0.2853(12) 0.022(3) Uiso 1 1 d . . .
H9B H -0.183(2) 0.9383(18) -0.4157(11) 0.020(3) Uiso 1 1 d . . .
H8B H -0.470(2) 1.097(2) -0.3230(12) 0.027(4) 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 N3 O4 123.68(9) . . ?
O3 N3 C4 117.69(9) . . ?
O4 N3 C4 118.62(9) . . ?
O2 N2 O1 123.63(9) . . ?
O2 N2 C2 117.93(9) . . ?
O1 N2 C2 118.34(9) . . ?
C1 N4 C10 124.00(9) . . y
C1 N4 C6 121.80(9) . . y
C10 N4 C6 114.06(8) . . ?
C5 N1 C1 119.58(9) . . ?
C3 C4 C5 119.29(10) . . ?
C3 C4 N3 120.13(10) . . ?
C5 C4 N3 120.38(10) . . ?
N1 C5 C4 122.54(10) . . ?
N4 C6 C7 111.37(9) . . ?
C2 C3 C4 117.63(10) . . ?
C3 C2 C1 120.20(9) . . ?
C3 C2 N2 116.26(9) . . y
C1 C2 N2 123.01(9) . . y
N4 C10 C9 110.49(9) . . ?
N4 C1 N1 117.26(9) . . y
N4 C1 C2 124.97(9) . . y
N1 C1 C2 117.73(9) . . ?
C8 C9 C10 112.16(9) . . ?
C9 C8 C7 109.54(9) . . ?
C6 C7 C8 110.04(9) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4 N3 1.2337(13) . ?
O2 N2 1.2303(13) . ?
O3 N3 1.2323(13) . ?
O1 N2 1.2329(13) . ?
N3 C4 1.4429(14) . ?
N2 C2 1.4556(13) . ?
N4 C1 1.3322(14) . ?
N4 C10 1.4709(13) . ?
N4 C6 1.4773(13) . ?
N1 C5 1.3164(15) . ?
N1 C1 1.3688(14) . ?
C4 C3 1.3832(15) . ?
C4 C5 1.4019(15) . ?
C6 C7 1.5231(15) . ?
C3 C2 1.3756(15) . ?
C2 C1 1.4402(14) . ?
C10 C9 1.5305(15) . ?
C9 C8 1.5240(15) . ?
C8 C7 1.5241(16) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 N3 C4 C3 173.87(9) . . . . y
O4 N3 C4 C3 -5.17(15) . . . . y
O3 N3 C4 C5 -11.26(14) . . . . y
O4 N3 C4 C5 169.70(9) . . . . y
C1 N1 C5 C4 -0.90(16) . . . . ?
C3 C4 C5 N1 -11.08(16) . . . . ?
N3 C4 C5 N1 174.01(10) . . . . ?
C1 N4 C6 C7 120.04(11) . . . . ?
C10 N4 C6 C7 -55.80(12) . . . . ?
C5 C4 C3 C2 7.25(15) . . . . ?
N3 C4 C3 C2 -177.82(9) . . . . ?
C4 C3 C2 C1 7.30(14) . . . . ?
C4 C3 C2 N2 -164.58(9) . . . . ?
O2 N2 C2 C3 -25.98(13) . . . . y
O1 N2 C2 C3 150.49(10) . . . . y
O2 N2 C2 C1 162.38(9) . . . . y
O1 N2 C2 C1 -21.15(14) . . . . y
C1 N4 C10 C9 -122.34(11) . . . . ?
C6 N4 C10 C9 53.40(12) . . . . ?
C10 N4 C1 N1 159.95(9) . . . . ?
C6 N4 C1 N1 -15.47(14) . . . . ?
C10 N4 C1 C2 -17.77(16) . . . . ?
C6 N4 C1 C2 166.81(9) . . . . ?
C5 N1 C1 N4 -162.47(10) . . . . ?
C5 N1 C1 C2 15.42(14) . . . . ?
C3 C2 C1 N4 158.80(10) . . . . ?
N2 C2 C1 N4 -29.88(15) . . . . ?
C3 C2 C1 N1 -18.92(14) . . . . ?
N2 C2 C1 N1 152.40(9) . . . . ?
N4 C10 C9 C8 -53.48(12) . . . . ?
C10 C9 C8 C7 55.81(12) . . . . ?
N4 C6 C7 C8 56.46(12) . . . . ?
C9 C8 C7 C6 -56.54(12) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 535823
