#------------------------------------------------------------------------------
#$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $
#$Revision: 32112 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/49/2004976.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_2004976
loop_
_publ_author_name
'Rowan, K. R.'
'Holt, E. M.'
_publ_section_title
;
 Dimethyl 2,6-Dimethyl-4-(3-nitrophenyl)-pyridine-3,5-dicarboxylate,
 Diethyl
 2,6-Dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate,
 and Diethyl 2,6-Dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1565
_journal_page_last               1570
_journal_volume                  52
_journal_year                    1996
_chemical_formula_moiety         'C19 H20 N2 O6'
_chemical_formula_sum            'C19 H20 N2 O6'
_chemical_formula_weight         372.37
_chemical_name_systematic
;
   diethyl 2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate
;
_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'
_cell_angle_alpha                90.00
_cell_angle_beta                 109.920(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.0180(10)
_cell_length_b                   19.517(2)
_cell_length_c                   8.6060(10)
_cell_measurement_reflns_used    53
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.008
_cell_measurement_theta_min      4.174
_cell_volume                     1897.8(4)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1991)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    'XP (Siemens, 1990)'
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Siemens P4 4-circle-diffractometer'
_diffrn_measurement_method       \q/2\q
_diffrn_radiation_monochromator  'highly oriented graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_sigmaI/netI    0.1105
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            2402
_diffrn_reflns_theta_max         20.0
_diffrn_reflns_theta_min         1.8
_diffrn_standards_decay_%        2.0
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            plate
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_description       clear
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.148
_refine_ls_extinction_coef       0.0016(11)
_refine_ls_extinction_method     'SHELXL93 (Sheldrick 1993)'
_refine_ls_goodness_of_fit_all   0.984
_refine_ls_goodness_of_fit_obs   1.134
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         1706
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.161
_refine_ls_restrained_S_obs      1.134
_refine_ls_R_factor_all          0.1452
_refine_ls_R_factor_obs          0.0587
_refine_ls_shift/esd_max         -0.003
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0500P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.1605
_refine_ls_wR_factor_obs         0.1064
_reflns_number_observed          890
_reflns_number_total             1767
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    fg1105.cif
_[local]_cod_data_source_block   III
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_cod_original_cell_volume        1897.8(3)
_cod_database_code               2004976
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,1/2+y,1/2-z
-x,-y,-z
x,1/2-y,1/2+z
loop_
_atom_site_label
_atom_site_occupancy
_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_refinement_flags
_atom_site_type_symbol
N1 1 .8611(6) .4858(3) .1636(8) .063(2) Uani d . N
H1A 1 .8039 .5156 .1631 .080 Uiso d R H
C2 1 .8301(6) .4265(5) .0794(9) .056(2) Uani d . C
C2' 1 .6999(5) .4178(4) -.0093(8) .076(2) Uani d . C
H2'A 1 .6577 .4567 .0104 .080 Uiso d R H
H2'B 1 .6855 .4136 -0.1257 .080 Uiso d R H
H2'C 1 .6734 .3771 .0300 .080 Uiso d R H
C3 1 .9168(6) .3799(4) .0775(8) .045(2) Uani d . C
C3' 1 .8852(6) .3182(4) -.0293(9) .052(2) Uani d . C
C3" 1 .7720(6) .2170(4) -.0896(10) .084(3) Uani d . C
H3"A 1 .7411 .2281 -0.2051 .080 Uiso d R H
H3"B 1 .8403 .1884 -0.0711 .080 Uiso d R H
C3'" 1 .6838(7) .1807(4) -.0432(10) .104(3) Uani d . C
H3'A 1 .6624 .1397 -0.1079 .080 Uiso d R H
H3'B 1 .7150 .1690 .0720 .080 Uiso d R H
H3'C 1 .6150 .2091 -0.0632 .080 Uiso d R H
O3' 1 .9289(4) .3041(2) -0.1301(6) .069(2) Uani d . O
O3" 1 .8055(4) .2795(2) .0063(5) .0607(14) Uani d . O
C4 1 1.0358(6) .3953(4) .1657(8) .042(2) Uani d . C
C5 1 1.0624(6) .4570(4) .2519(8) .049(2) Uani d . C
C5' 1 1.1870(6) .4758(4) .3504(9) .049(2) Uani d . C
C5" 1 1.3485(6) .4491(4) .5981(10) .098(3) Uani d . C
H5"A 1 1.3624 .4976 .6078 .080 Uiso d R H
H5"B 1 1.3557 .4314 .7051 .080 Uiso d R H
C5"' 1 1.4337(7) .4160(4) .5364(11) .121(3) Uani d . C
H5"C 1 1.5123 .4246 .6116 .080 Uiso d R H
H5"D 1 1.4193 .3676 .5275 .080 Uiso d R H
H5"E 1 1.4260 .4343 .4296 .080 Uiso d R H
O5" 1 1.2294(4) .4347(3) .4785(6) .073(2) Uani d . O
O5' 1 1.2399(4) .5232(2) .3211(6) .079(2) Uani d . O
C6 1 .9733(7) .5018(4) .2481(9) .056(2) Uani d . C
C6' 1 .9968(6) .5685(3) .3428(9) .070(2) Uani d . C
H6'A .50 .9241 .5930 .3249 .080 Uiso d PR H
H6'B .50 1.0334 .5590 .4585 .080 Uiso d PR H
H6'C .50 1.0492 .5959 .3056 .080 Uiso d PR H
C7 1 1.1307(5) .3458(4) .1698(8) .045(2) Uani d . C
C8 1 1.1272(6) .2780(4) .2207(8) .062(2) Uani d . C
H8A 1 1.0624 .2632 .2537 .080 Uiso d R H
C9 1 1.2155(8) .2323(4) .2240(10) .081(3) Uani d . C
H9A 1 1.2109 .1858 .2577 .080 Uiso d R H
C10 1 1.3093(7) .2527(5) .1802(10) .072(2) Uani d . C
H10A 1 1.3714 .2212 .1834 .080 Uiso d R H
C11 1 1.3113(6) .3186(5) .1319(9) .058(2) Uani d . C
C12 1 1.2243(6) .3654(3) .1221(7) .048(2) Uani d . C
H12A 1 1.2281 .4109 .0821 .080 Uiso d R H
N2 1 1.4115(6) .3410(4) .0798(9) .083(2) Uani d . N
O1 1 1.4221(6) .4009(4) .0577(11) .151(4) Uani d . O
O2 1 1.4805(5) .2976(3) .0704(8) .118(2) Uani d . O
H6'E .50 .9680 .6013 .2058 .050 Uiso d P H
H6'D .50 .9364 .5811 .4164 .050 Uiso d P H
H6'F .50 1.1137 .5811 .4209 .050 Uiso d P H
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
N1 0.060(5) 0.062(5) 0.086(5) 0.022(4) 0.048(4) 0.014(4)
C2 0.051(5) 0.065(6) 0.060(5) -0.007(5) 0.029(4) 0.004(5)
C2' 0.052(5) 0.082(6) 0.092(6) 0.010(4) 0.022(5) 0.018(5)
C3 0.039(5) 0.049(5) 0.058(5) -0.001(4) 0.029(4) 0.012(4)
C3' 0.035(4) 0.069(6) 0.056(6) -0.012(4) 0.020(4) 0.001(5)
C3" 0.079(6) 0.092(7) 0.080(6) -0.034(5) 0.026(5) -0.014(6)
C3'" 0.110(7) 0.086(7) 0.106(7) -0.024(6) 0.024(6) -0.022(6)
O3' 0.073(4) 0.083(4) 0.064(4) -0.015(3) 0.040(3) -0.005(3)
O3" 0.063(3) 0.063(3) 0.058(3) -0.022(3) 0.023(3) -0.008(3)
C4 0.045(5) 0.051(5) 0.040(4) -0.005(4) 0.026(4) 0.008(4)
C5 0.038(5) 0.057(5) 0.049(5) -0.004(4) 0.013(4) 0.005(5)
C5' 0.060(6) 0.050(5) 0.041(5) 0.006(5) 0.022(5) 0.005(5)
C5" 0.063(6) 0.131(8) 0.102(7) 0.009(6) 0.031(6) 0.006(6)
C5"' 0.111(7) 0.102(7) 0.129(8) -0.038(6) 0.013(7) 0.023(7)
O5" 0.045(3) 0.093(4) 0.069(4) -0.013(3) 0.006(3) 0.015(4)
O5' 0.069(3) 0.063(4) 0.100(5) -0.022(3) 0.022(3) 0.013(3)
C6 0.041(5) 0.072(6) 0.059(5) 0.009(5) 0.023(5) 0.018(5)
C6' 0.085(5) 0.051(5) 0.090(6) 0.004(4) 0.053(5) -0.010(5)
C7 0.030(4) 0.053(5) 0.052(5) 0.001(4) 0.015(4) -0.006(4)
C8 0.055(5) 0.067(6) 0.063(6) -0.009(5) 0.020(4) 0.008(5)
C9 0.085(6) 0.048(5) 0.098(7) 0.010(6) 0.015(6) 0.011(5)
C10 0.052(6) 0.077(8) 0.088(7) 0.018(5) 0.026(5) 0.001(5)
C11 0.037(5) 0.071(6) 0.071(6) -0.004(5) 0.023(4) -0.006(5)
C12 0.046(4) 0.045(5) 0.050(5) 0.007(4) 0.013(4) 0.000(4)
N2 0.054(5) 0.098(6) 0.095(6) 0.021(5) 0.024(4) -0.006(5)
O1 0.099(5) 0.126(6) 0.276(10) 0.025(5) 0.127(6) 0.063(7)
O2 0.065(4) 0.146(6) 0.159(6) 0.008(4) 0.058(4) -0.027(5)
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
C6 N1 C2 122.5(6) no
N1 C2 C3 119.9(6) no
N1 C2 C2' 114.9(7) no
C3 C2 C2' 125.3(8) no
C2 C3 C4 118.9(7) no
C2 C3 C3' 120.3(7) no
C4 C3 C3' 120.5(6) no
O3' C3' O3" 124.6(8) no
O3' C3' C3 123.8(7) no
O3" C3' C3 111.6(6) no
C3'" C3" O3" 110.1(6) no
C3' O3" C3" 115.2(6) no
C5 C4 C3 118.7(6) no
C5 C4 C7 121.0(6) no
C3 C4 C7 120.3(6) no
C6 C5 C4 120.1(6) no
C6 C5 C5' 118.7(7) no
C4 C5 C5' 121.2(6) no
O5' C5' O5" 124.4(7) no
O5' C5' C5 124.9(7) no
O5" C5' C5 110.6(6) no
C5"' C5" O5" 107.2(7) no
C5' O5" C5" 118.2(6) no
N1 C6 C5 119.9(7) no
N1 C6 C6' 117.7(7) no
C5 C6 C6' 122.3(7) no
C12 C7 C8 118.1(6) no
C12 C7 C4 120.7(6) no
C8 C7 C4 121.2(6) no
C9 C8 C7 120.8(7) no
C10 C9 C8 120.6(7) no
C11 C10 C9 117.6(7) no
C10 C11 C12 124.0(7) no
C10 C11 N2 118.2(8) no
C12 C11 N2 117.8(8) no
C11 C12 C7 118.8(6) no
O1 N2 O2 124.1(9) no
O1 N2 C11 118.4(8) no
O2 N2 C11 117.4(8) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C6 1.333(7) yes
N1 C2 1.348(8) yes
C2 C3 1.388(8) yes
C2 C2' 1.498(8) yes
C3 C4 1.405(8) yes
C3 C3' 1.484(9) yes
C3' O3' 1.190(7) yes
C3' O3" 1.335(7) yes
C3" C3'" 1.441(8) yes
C3" O3" 1.451(7) yes
C4 C5 1.393(8) yes
C4 C7 1.486(8) yes
C5 C6 1.375(8) yes
C5 C5' 1.493(8) yes
C5' O5' 1.197(7) yes
C5' O5" 1.318(7) yes
C5" C5"' 1.456(9) yes
C5" O5" 1.478(8) yes
C6 C6' 1.510(8) yes
C7 C12 1.376(7) no
C7 C8 1.400(8) no
C8 C9 1.378(9) no
C9 C10 1.364(9) no
C10 C11 1.355(8) no
C11 C12 1.369(8) no
C11 N2 1.486(9) no
N2 O1 1.197(7) no
N2 O2 1.208(7) no
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_publ_flag
C6 N1 C2 C3 -0.6(10) yes
C6 N1 C2 C2' -179.5(6) no
N1 C2 C3 C4 0.7(9) yes
C2' C2 C3 C4 179.4(6) no
N1 C2 C3 C3' -173.2(6) no
C2' C2 C3 C3' 5.5(10) no
C2 C3 C3' O3' 123.8(8) no
C4 C3 C3' O3' -50.0(10) no
C2 C3 C3' O3" -58.6(8) no
C4 C3 C3' O3" 127.6(6) no
O3' C3' O3" C3" -0.8(10) no
C3 C3' O3" C3" -178.4(5) no
C3'" C3" O3" C3' -178.6(6) no
C2 C3 C4 C5 0.0(9) yes
C3' C3 C4 C5 173.9(6) no
C2 C3 C4 C7 178.5(6) no
C3' C3 C4 C7 -7.6(9) no
C3 C4 C5 C6 -0.8(9) yes
C7 C4 C5 C6 -179.3(6) no
C3 C4 C5 C5' 178.9(6) no
C7 C4 C5 C5' 0.5(9) no
C6 C5 C5' O5' -64.8(9) no
C4 C5 C5' O5' 115.5(8) no
C6 C5 C5' O5" 112.5(7) no
C4 C5 C5' O5" -67.2(8) no
O5' C5' O5" C5" 2.3(10) no
C5 C5' O5" C5" -175.0(6) no
C5"' C5" O5" C5' -86.2(8) no
C2 N1 C6 C5 -0.2(10) yes
C2 N1 C6 C6' -177.7(6) no
C4 C5 C6 N1 0.9(10) yes
C5' C5 C6 N1 -178.8(6) no
C4 C5 C6 C6' 178.4(6) no
C5' C5 C6 C6' -1.4(10) no
C5 C4 C7 C12 -56.6(8) no
C3 C4 C7 C12 125.0(6) no
C5 C4 C7 C8 124.0(7) no
C3 C4 C7 C8 -54.4(8) yes
C12 C7 C8 C9 0.5(10) no
C4 C7 C8 C9 179.9(7) no
C7 C8 C9 C10 1.0(12) no
C8 C9 C10 C11 -0.8(12) no
C9 C10 C11 C12 -1.1(12) no
C9 C10 C11 N2 -178.5(6) no
C10 C11 C12 C7 2.6(11) no
N2 C11 C12 C7 -180.0(6) no
C8 C7 C12 C11 -2.2(9) no
C4 C7 C12 C11 178.3(6) no
C10 C11 N2 O1 -170.5(9) no
C12 C11 N2 O1 12.0(11) no
C10 C11 N2 O2 6.0(11) no
C12 C11 N2 O2 -171.6(7) no