#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/59/2005947.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_2005947
loop_
_publ_author_name
'Rowan, K. R.'
'Holt, E. M.'
_publ_section_title
;
 3-Ethoxycarbonyl-5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)pyridinium
 Nitrate, Dineopentyl
 2,6-Dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate and Dihexyl
 2,6-Dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              257
_journal_page_last               261
_journal_paper_doi               10.1107/S010827019601181X
_journal_volume                  53
_journal_year                    1997
_chemical_formula_iupac          'C18 H19 N2 O6 1+, N O3 1-'
_chemical_formula_moiety         'C18 H19 N3 O9'
_chemical_formula_sum            'C18 H19 N3 O9'
_chemical_formula_weight         421.36
_chemical_name_systematic
;
ethyl methyl 2,6-dimethyl-4-(3-nitrophenyl)pyridinium-3,5-dicarboxylate
nitrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                78.71(1)
_cell_angle_beta                 71.05(1)
_cell_angle_gamma                69.40(1)
_cell_formula_units_Z            2
_cell_length_a                   9.034(1)
_cell_length_b                   10.228(1)
_cell_length_c                   12.392(2)
_cell_measurement_reflns_used    66
_cell_measurement_temperature    298
_cell_measurement_theta_max      12.43
_cell_measurement_theta_min      3.69
_cell_volume                     1009.4(2)
_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      298
_diffrn_measurement_device       'Syntex P4 4-circle'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  'highly oriented graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4289
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         2.14
_diffrn_standards_decay_%        insignificant
_diffrn_standards_interval_time  97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.1057
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rhombohedral
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.253
_refine_ls_extinction_coef       0.029(5)
_refine_ls_extinction_method     'SHELXL93 (Sheldrick, 1993)'
_refine_ls_goodness_of_fit_obs   0.898
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         3552
_refine_ls_R_factor_obs          .0579
_refine_ls_shift/esd_max         0.032
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
;
calc w = 1/[\s^2^(F~o~^2^) + (0.1127P)^2^ + 0.3691P] where
P = (F~o~^2^ + 2F~c~^2^)/3
;
_refine_ls_wR_factor_obs         .1494
_reflns_number_observed          3501
_reflns_number_total             3552
_reflns_observed_criterion       F>2.0\s(F)
_cod_data_source_file            pa1238.cif
_cod_data_source_block           holt1
_cod_database_code               2005947
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
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_calc_attached_atom
N(1) 0.1663(3) 0.1132(3) 0.0487(2) 0.062(1) Uani d .
H(1A) 0.1281(4) 0.1474(3) -0.0192(2) 0.080 Uiso calc R
N(2) 0.2033(5) -0.0843(4) 0.6459(2) 0.078(1) Uani d .
N(3) -0.0048(6) 0.3074(5) 0.8261(3) 0.084(1) Uani d .
O(1) 0.2440(4) -0.1624(4) 0.7254(2) 0.113(1) Uani d .
O(2) 0.0716(4) 0.0094(4) 0.6565(2) 0.093(1) Uani d .
O(3) 0.0949(10) 0.2020(9) 0.8501(5) 0.104(4) Uani d .
O(4) -0.1370(6) 0.3577(7) 0.9055(5) 0.094(2) Uani d .
O(5) 0.0054(18) 0.3670(13) 0.7317(9) 0.123(4) Uani d .
O(6) 0.1339(14) 0.312(2) 0.8262(12) 0.128(5) Uani d .
O(7) -0.030(4) 0.215(3) 0.8968(14) 0.181(15) Uani d .
O(8) -0.044(4) 0.368(4) 0.748(2) 0.185(14) Uani d .
C(2) 0.2649(4) -0.0213(4) 0.0472(3) 0.061(1) Uani d .
C(2') 0.2907(6) -0.0974(4) -0.0517(3) 0.085(1) Uani d .
H(2'A) 0.2328(6) -0.0355(4) -0.1041(3) 0.080 Uiso calc R
H(2'B) 0.4061(6) -0.1297(4) -0.0903(3) 0.080 Uiso calc R
H(2'C) 0.2500(6) -0.1763(4) -0.0244(3) 0.080 Uiso calc R
C(3) 0.3321(4) -0.0798(3) 0.1384(2) 0.056(1) Uani d .
C(3') 0.4433(5) -0.2276(4) 0.1327(3) 0.070(1) Uani d .
C(3") 0.4851(9) -0.4595(5) 0.2154(6) 0.149(3) Uani d .
H(3"A) 0.4340(9) -0.5126(5) 0.2804(6) 0.080 Uiso calc .
H(3"B) 0.4928(9) -0.4935(5) 0.1462(6) 0.080 Uiso calc R
H(3"C) 0.5935(9) -0.4695(5) 0.2183(6) 0.080 Uiso calc R
O(3') 0.5690(4) -0.2623(3) 0.0581(3) 0.109(1) Uani d .
O(3") 0.3859(4) -0.3106(3) 0.2168(2) 0.092(1) Uani d .
C(4) 0.2964(4) 0.0012(3) 0.2278(2) 0.052(1) Uani d .
C(5) 0.1969(4) 0.1395(3) 0.2228(2) 0.053(1) Uani d .
C(5') 0.1615(5) 0.2333(3) 0.3131(3) 0.062(1) Uani d .
C(5") -0.0383(7) 0.3554(5) 0.4621(4) 0.110(2) Uani d .
H(5"A) 0.0137(7) 0.4273(5) 0.4323(4) 0.080 Uiso calc R
H(5"E) -0.0037(7) 0.3048(5) 0.5281(4) 0.080 Uiso calc R
C(5"') -0.1928(11) 0.4136(8) 0.4959(6) 0.179(4) Uani d .
H(5"B) -0.2287(11) 0.4776(8) 0.5533(6) 0.080 Uiso calc R
H(5"C) -0.2250(11) 0.4630(8) 0.4288(6) 0.080 Uiso calc R
H(5"D) -0.2424(11) 0.3401(8) 0.5250(6) 0.080 Uiso calc R
O(5') 0.2646(3) 0.2740(3) 0.3245(2) 0.087(1) Uani d .
O(5") 0.0063(3) 0.2635(2) 0.3755(2) 0.073(1) Uani d .
C(6) 0.1317(4) 0.1962(3) 0.1299(3) 0.057(1) Uani d .
C(6') 0.0304(5) 0.3437(4) 0.1132(3) 0.078(1) Uani d .
H(6'A) -0.0013(5) 0.3578(4) 0.0439(3) 0.080 Uiso calc R
H(6'B) -0.0663(5) 0.3662(4) 0.1769(3) 0.080 Uiso calc R
H(6'C) 0.0949(5) 0.4034(4) 0.1072(3) 0.080 Uiso calc R
C(7) 0.3618(4) -0.0598(3) 0.3296(3) 0.052(1) Uani d .
C(8) 0.5285(4) -0.1311(3) 0.3171(3) 0.065(1) Uani d .
H(8A) 0.6025(4) -0.1394(3) 0.2412(3) 0.080 Uiso calc R
C(9) 0.5870(5) -0.1861(4) 0.4110(4) 0.075(1) Uani d .
H(9A) 0.7019(5) -0.2365(4) 0.4004(4) 0.080 Uiso calc R
C(10) 0.4812(5) -0.1741(4) 0.5195(3) 0.069(1) Uani d .
H(10A) 0.5226(5) -0.2115(4) 0.5851(3) 0.080 Uiso calc R
C(11) 0.3183(4) -0.1033(3) 0.5314(3) 0.059(1) Uani d .
C(12) 0.2564(4) -0.0456(3) 0.4382(2) 0.055(1) Uani d .
H(12A) 0.1412(4) 0.0037(3) 0.4491(2) 0.080 Uiso calc R
C(99") 0.567(4) -0.496(4) 0.291(3) 0.08(1) Uiso d .
H(99D) 0.6659(42) -0.4700(36) 0.2599(31) 0.080 Uiso calc R
H(99E) 0.5004(42) -0.4478(36) 0.3583(31) 0.080 Uiso calc R
H(99F) 0.5946(42) -0.5953(36) 0.3113(31) 0.080 Uiso calc R
C(99') 0.504(6) -0.536(5) 0.143(4) 0.07(2) Uiso d .
H(99G) 0.6075(62) -0.5415(53) 0.0865(40) 0.080 Uiso calc R
H(99H) 0.5048(62) -0.6287(53) 0.1788(40) 0.080 Uiso calc R
H(99I) 0.4163(62) -0.4973(53) 0.1077(40) 0.080 Uiso calc R
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.0 0.0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H 0.0 0.0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N 0.0 0.0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O 0.0 0.0 '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
C(6) N(1) C(2) 124.9(3) no
O(1) N(2) O(2) 123.4(4) no
O(1) N(2) C(11) 118.0(4) no
O(2) N(2) C(11) 118.5(3) no
O(8) N(3) O(7) 140(2) no
O(3) N(3) O(5) 124.7(8) no
O(8) N(3) O(6) 112(2) no
O(7) N(3) O(6) 104.8(13) no
O(3) N(3) O(4) 118.1(5) no
O(5) N(3) O(4) 117.1(7) no
N(1) C(2) C(3) 118.1(3) no
N(1) C(2) C(2') 117.2(3) no
C(3) C(2) C(2') 124.7(3) no
C(2) C(3) C(4) 119.5(3) no
C(2) C(3) C(3') 116.7(3) no
C(4) C(3) C(3') 123.8(3) no
O(3') C(3') O(3") 125.6(4) no
O(3') C(3') C(3) 122.6(3) no
O(3") C(3') C(3) 111.8(3) no
C(99') C(3") C(99") 124(3) no
C(99') C(3") O(3") 125(3) no
C(99") C(3") O(3") 111(2) no
C(3') O(3") C(3") 115.4(4) no
C(5) C(4) C(3) 119.4(3) no
C(5) C(4) C(7) 119.5(3) no
C(3) C(4) C(7) 121.1(3) no
C(4) C(5) C(6) 120.0(3) no
C(4) C(5) C(5') 121.7(3) no
C(6) C(5) C(5') 118.3(3) no
O(5') C(5') O(5") 125.9(3) no
O(5') C(5') C(5) 122.6(4) no
O(5") C(5') C(5) 111.5(3) no
C(5"') C(5") O(5") 112.2(5) no
C(5') O(5") C(5") 114.9(3) no
N(1) C(6) C(5) 118.1(3) no
N(1) C(6) C(6') 117.3(3) no
C(5) C(6) C(6') 124.6(3) no
C(12) C(7) C(8) 118.7(3) no
C(12) C(7) C(4) 119.8(3) no
C(8) C(7) C(4) 121.5(3) no
C(9) C(8) C(7) 121.0(3) no
C(10) C(9) C(8) 120.4(3) no
C(11) C(10) C(9) 118.4(3) no
C(10) C(11) C(12) 122.4(3) no
C(10) C(11) N(2) 119.8(3) no
C(12) C(11) N(2) 117.9(3) no
C(7) C(12) C(11) 119.2(3) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N(1) . C(6) . 1.332(4) yes
N(1) . C(2) . 1.351(4) yes
N(2) . O(1) . 1.210(4) yes
N(2) . O(2) . 1.224(4) yes
N(2) . C(11) . 1.463(5) yes
N(3) . O(8) . 1.13(2) yes
N(3) . O(7) . 1.19(2) yes
N(3) . O(3) . 1.195(7) yes
N(3) . O(5) . 1.199(11) yes
N(3) . O(6) . 1.271(12) yes
N(3) . O(4) . 1.290(6) yes
C(2) . C(3) . 1.389(4) yes
C(2) . C(2') . 1.491(5) yes
C(3) . C(4) . 1.399(4) yes
C(3) . C(3') . 1.492(5) yes
C(3') . O(3') . 1.197(4) yes
C(3') . O(3") . 1.298(4) yes
C(3") . C(99') . 1.23(5) yes
C(3") . C(99") . 1.30(3) yes
C(3") . O(3") . 1.471(5) yes
C(4) . C(5) . 1.386(4) yes
C(4) . C(7) . 1.500(4) yes
C(5) . C(6) . 1.395(4) yes
C(5) . C(5') . 1.499(4) yes
C(5') . O(5') . 1.201(4) yes
C(5') . O(5") . 1.321(4) yes
C(5") . C(5"') . 1.269(8) yes
C(5") . O(5") . 1.430(4) yes
C(6) . C(6') . 1.478(4) yes
C(7) . C(12) . 1.373(4) yes
C(7) . C(8) . 1.394(4) yes
C(8) . C(9) . 1.372(5) yes
C(9) . C(10) . 1.373(5) yes
C(10) . C(11) . 1.365(5) yes
C(11) . C(12) . 1.384(4) yes
