#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006524.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_2006524
loop_
_publ_author_name
'Cole, J. M.'
'Howard, J. A. K.'
'MacBride, J. A. H.'
_publ_section_title
;
 3,5-Dinitro-2-{[(<i>R</i>)-({-})-1-phenylethyl]amino}pyridine
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1331
_journal_page_last               1334
_journal_volume                  53
_journal_year                    1997
_chemical_formula_sum            'C13 H12 N4 O4'
_chemical_formula_weight         288.27
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 93.689(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.3890(10)
_cell_length_b                   8.5800(10)
_cell_length_c                   8.9340(10)
_cell_measurement_reflns_used    497
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      20.75
_cell_measurement_theta_min      3.22
_cell_volume                     641.72(13)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_molecular_graphics    'SHELXTL-Plus (Sheldrick, 1991)'
_computing_publication_material  SHELXL-93
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measurement_device       'Siemens SMART-CCD diffractometer'
_diffrn_measurement_method       '\w 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  0.0548
_diffrn_reflns_av_sigmaI/netI    0.0471
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2576
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         2.28
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.114
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular plate'
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.228
_refine_ls_abs_structure_details
'established by synthesis [Flack (1983) parameter not determinate]'
_refine_ls_abs_structure_Flack   -2.(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.169
_refine_ls_goodness_of_fit_obs   1.115
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         1713
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.389
_refine_ls_restrained_S_obs      1.114
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_obs          0.0449
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0334P)^2^+0.5637P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1276
_refine_ls_wR_factor_obs         0.0971
_reflns_number_observed          1566
_reflns_number_total             1723
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    na1281.cif
_[local]_cod_data_source_block   1
_cod_original_cell_volume        641.7(2)
_cod_database_code               2006524
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0248(14) 0.026(2) 0.042(2) 0.0051(13) 0.0112(13) 0.0047(13)
O2 0.0319(15) 0.029(2) 0.037(2) 0.0078(13) 0.0035(12) 0.0098(14)
O3 0.0310(14) 0.029(2) 0.0290(14) 0.0003(14) 0.0071(11) 0.0033(14)
O4 0.0188(13) 0.029(2) 0.042(2) 0.0035(13) -0.0039(11) -0.0009(13)
N1 0.024(2) 0.018(2) 0.031(2) 0.0012(14) 0.0029(14) 0.0042(14)
N2 0.022(2) 0.019(2) 0.025(2) -0.0013(15) -0.0002(14) 0.0002(14)
N3 0.030(2) 0.020(2) 0.026(2) -0.0001(15) -0.0002(14) 0.0022(15)
N4 0.027(2) 0.023(2) 0.025(2) -0.005(2) 0.0029(13) -0.005(2)
C1 0.025(2) 0.022(2) 0.018(2) 0.002(2) -0.0022(14) 0.004(2)
C2 0.027(2) 0.019(2) 0.024(2) -0.007(2) -0.0024(15) 0.000(2)
C3 0.022(2) 0.026(3) 0.027(2) 0.000(2) -0.0010(15) 0.001(2)
C4 0.029(2) 0.023(2) 0.030(2) 0.005(2) 0.005(2) 0.008(2)
C5 0.035(2) 0.025(2) 0.022(2) 0.002(2) 0.002(2) 0.001(2)
C6 0.025(2) 0.019(2) 0.027(2) -0.004(2) 0.001(2) 0.001(2)
C7 0.022(2) 0.021(2) 0.025(2) 0.000(2) -0.0003(15) 0.002(2)
C8 0.027(2) 0.028(3) 0.026(2) 0.002(2) 0.001(2) -0.001(2)
C9 0.019(2) 0.022(2) 0.022(2) -0.002(2) -0.0023(14) -0.001(2)
C10 0.020(2) 0.017(2) 0.022(2) 0.003(2) -0.0010(14) -0.0012(14)
C11 0.023(2) 0.018(2) 0.021(2) -0.001(2) -0.0022(14) -0.002(2)
C12 0.019(2) 0.020(2) 0.025(2) 0.000(2) -0.0007(14) -0.005(2)
C13 0.024(2) 0.023(2) 0.026(2) 0.001(2) 0.000(2) -0.002(2)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_type_symbol
O1 -0.1566(3) 0.9649(4) 0.7299(3) 0.0307(7) Uani d 1 O
O2 -0.0182(3) 1.0684(4) 0.5592(3) 0.0326(7) Uani d 1 O
O3 0.5153(3) 0.8907(4) 0.4943(3) 0.0295(7) Uani d 1 O
O4 0.6102(3) 0.6964(4) 0.6283(3) 0.0300(7) Uani d 1 O
N1 -0.0816(4) 0.6743(4) 0.8228(4) 0.0244(8) Uani d 1 N
H1N -0.151(5) 0.739(6) 0.808(5) 0.029 Uiso d 1 H
N2 0.1773(3) 0.6038(4) 0.7886(3) 0.0221(8) Uani d 1 N
N3 -0.0391(4) 0.9658(4) 0.6528(3) 0.0252(8) Uani d 1 N
N4 0.4996(4) 0.7843(4) 0.5843(3) 0.0249(8) Uani d 1 N
C1 -0.2451(4) 0.5561(5) 1.0062(4) 0.0220(9) Uani d 1 C
C2 -0.3860(4) 0.4728(5) 1.0004(4) 0.0236(9) Uani d 1 C
H2 -0.404(5) 0.397(6) 0.934(5) 0.028 Uiso d 1 H
C3 -0.5051(5) 0.5040(5) 1.0990(4) 0.0251(9) Uani d 1 C
H3 -0.610(5) 0.437(5) 1.089(4) 0.030 Uiso d 1 H
C4 -0.4795(5) 0.6182(5) 1.2074(4) 0.0272(9) Uani d 1 C
H4 -0.569(5) 0.643(5) 1.283(5) 0.033 Uiso d 1 H
C5 -0.3371(5) 0.7024(5) 1.2167(4) 0.0272(9) Uani d 1 C
H5 -0.309(5) 0.780(6) 1.298(5) 0.033 Uiso d 1 H
C6 -0.2224(5) 0.6731(5) 1.1147(4) 0.0241(9) Uani d 1 C
H6 -0.128(5) 0.732(5) 1.121(5) 0.029 Uiso d 1 H
C7 -0.1131(5) 0.5259(5) 0.8989(4) 0.0230(9) Uani d 1 C
H7 -0.015(5) 0.505(5) 0.961(4) 0.028 Uiso d 1 H
C8 -0.1526(5) 0.3981(5) 0.7838(4) 0.0268(9) Uani d 1 C
H8A -0.161(5) 0.294(6) 0.846(5) 0.040 Uiso d 1 H
H8B -0.069(6) 0.385(6) 0.713(5) 0.040 Uiso d 1 H
H8C -0.253(6) 0.423(6) 0.720(5) 0.040 Uiso d 1 H
C9 0.0574(4) 0.7090(5) 0.7635(4) 0.0207(8) Uani d 1 C
C10 0.0824(4) 0.8462(5) 0.6760(4) 0.0200(8) Uani d 1 C
C11 0.2243(4) 0.8695(5) 0.6132(4) 0.0207(9) Uani d 1 C
H11 0.243(5) 0.969(6) 0.559(4) 0.025 Uiso d 1 H
C12 0.3437(4) 0.7593(5) 0.6420(4) 0.0215(9) Uani d 1 C
C13 0.3165(5) 0.6315(5) 0.7310(4) 0.0244(9) Uani d 1 C
H13 0.408(5) 0.548(5) 0.752(4) 0.029 Uiso d 1 H
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_publ_flag
N3 O1 H1N 101.0(10) ?
C9 N1 C7 123.9(3) yes
C9 N1 H1N 114(3) ?
C7 N1 H1N 122(3) ?
C13 N2 C9 118.5(3) ?
O2 N3 O1 122.3(3) yes
O2 N3 C10 118.1(3) yes
O1 N3 C10 119.5(3) yes
O3 N4 O4 123.3(3) yes
O3 N4 C12 118.6(3) yes
O4 N4 C12 118.0(3) yes
C2 C1 C6 118.4(4) ?
C2 C1 C7 122.7(4) ?
C6 C1 C7 118.9(4) ?
C1 C2 C3 121.5(4) ?
C1 C2 H2 121(3) ?
C3 C2 H2 118(3) ?
C4 C3 C2 119.4(4) ?
C4 C3 H3 123(2) ?
C2 C3 H3 118(2) ?
C3 C4 C5 120.1(4) ?
C3 C4 H4 120(2) ?
C5 C4 H4 120(2) ?
C6 C5 C4 119.6(4) ?
C6 C5 H5 117(3) ?
C4 C5 H5 123(2) ?
C5 C6 C1 121.0(4) ?
C5 C6 H6 119(3) ?
C1 C6 H6 121(3) ?
N1 C7 C8 110.3(3) ?
N1 C7 C1 107.5(3) ?
C8 C7 C1 114.1(3) ?
N1 C7 H7 104(3) ?
C8 C7 H7 113(3) ?
C1 C7 H7 107(2) ?
C7 C8 H8A 106(3) ?
C7 C8 H8B 113(3) ?
H8A C8 H8B 108(4) ?
C7 C8 H8C 112(3) ?
H8A C8 H8C 113(4) ?
H8B C8 H8C 106(3) ?
N1 C9 N2 116.1(4) yes
N1 C9 C10 123.8(3) yes
N2 C9 C10 120.1(3) ?
C11 C10 C9 120.4(3) ?
C11 C10 N3 117.5(3) yes
C9 C10 N3 122.1(3) yes
C10 C11 C12 117.6(4) ?
C10 C11 H11 120(2) ?
C12 C11 H11 122(2) ?
C13 C12 C11 120.2(3) ?
C13 C12 N4 120.5(3) yes
C11 C12 N4 119.3(3) yes
N2 C13 C12 123.2(4) ?
N2 C13 H13 117(2) ?
C12 C13 H13 120(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 N3 1.238(4) yes
O1 H1N 2.06(5) ?
O2 N3 1.234(4) yes
O3 N4 1.229(4) yes
O4 N4 1.240(4) yes
N1 C9 1.345(5) yes
N1 C7 1.476(5) yes
N1 H1N 0.81(5) ?
N2 C13 1.327(5) yes
N2 C9 1.359(5) yes
N3 C10 1.452(5) yes
N4 C12 1.452(5) yes
C1 C2 1.379(5) ?
C1 C6 1.400(6) ?
C1 C7 1.532(5) ?
C2 C3 1.400(6) ?
C2 H2 0.89(5) ?
C3 C4 1.385(6) ?
C3 H3 1.05(4) ?
C4 C5 1.394(6) ?
C4 H4 1.06(4) ?
C5 C6 1.390(6) ?
C5 H5 1.00(5) ?
C6 H6 0.94(5) ?
C7 C8 1.525(6) ?
C7 H7 0.98(4) ?
C8 H8A 1.06(5) ?
C8 H8B 0.99(5) ?
C8 H8C 1.01(5) ?
C9 C10 1.436(5) yes
C10 C11 1.363(5) yes
C11 C12 1.388(5) yes
C11 H11 1.00(5) ?
C12 C13 1.382(6) yes
C13 H13 1.06(4) ?