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/
Crampton, Michael R.; Emokpae, Thomas A.; Howard, Judith A. K.; Isanbor, Chukwuemeka; Mondal, Raju; Organic & Biomolecular Chemistry 1 (2003) 1004–; doi:10.1039/b211639c

data_7150481
_publ_section_title
;
 Kinetic and equilibrium studies of \s-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 &amp;  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/[\s^2^(Fo^2^)+(0.0557P)^2^+0.1288P] where P=(Fo^2^+2Fc^2^)/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>2\s(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