#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/21/2012173.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_2012173
loop_
_publ_author_name
'Vrábel, Viktor'
'Lehotay, Jozef'
'Oktavec, Drahomír'
'Marchalín, Štefan'
_publ_section_title
;3-Methyl 5-isopropyl
 2-methoxyiminomethyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1073
_journal_page_last               1074
_journal_paper_doi               10.1107/S0108270101009313
_journal_volume                  57
_journal_year                    2001
_chemical_formula_moiety         'C20 H23 N3 O7'
_chemical_formula_sum            'C20 H23 N3 O7'
_chemical_formula_weight         417.41
_chemical_name_systematic
;
Methyl isopropyl 2-methoxyiminomethyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydro-
pyridine-3,5-dicarboxylate
;
_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                93.99(4)
_cell_angle_beta                 105.09(4)
_cell_angle_gamma                103.66(4)
_cell_formula_units_Z            2
_cell_length_a                   9.563(4)
_cell_length_b                   9.703(4)
_cell_length_c                   12.031(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.4
_cell_measurement_theta_min      8.2
_cell_volume                     1037.1(9)
_computing_cell_refinement       'Syntex P2₁ software'
_computing_data_collection       'Syntex P2₁ software'
_computing_data_reduction        'XP21   (Pavelčík, 1987)'
_computing_molecular_graphics    'ORTEPII  (Johnson, 1976)'
_computing_publication_material  SHELXS97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .958
_diffrn_measured_fraction_theta_max .958
_diffrn_measurement_device_type  'Syntex P2₁ diffractometer'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71069
_diffrn_reflns_av_R_equivalents  .0000
_diffrn_reflns_av_sigmaI/netI    .1988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3527
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         1.77
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  100
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    .102
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_meas      1.340(10)
_exptl_crystal_density_method    'flotation in bromoform-hexane'
_exptl_crystal_description       plate
_exptl_crystal_F_000             440
_exptl_crystal_size_max          .35
_exptl_crystal_size_mid          .30
_exptl_crystal_size_min          .10
_refine_diff_density_max         .136
_refine_diff_density_min         -.135
_refine_ls_extinction_coef       .0088(6)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   .783
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         3527
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      .783
_refine_ls_R_factor_all          .1919
_refine_ls_R_factor_gt           .0518
_refine_ls_shift/su_max          .002
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0112P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .0680
_reflns_number_gt                1209
_reflns_number_total             3527
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            av1077.cif
_cod_data_source_block           I
_cod_original_cell_volume        1037.1(8)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2012173
_cod_database_fobs_code          2012173
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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 .6623(2) .3899(2) .99646(18) .0689(7) Uani d . 1 . . O
O2 .3579(2) -.1862(2) .64941(18) .0682(7) Uani d . 1 . . O
O3 .5089(2) .0319(2) .69399(18) .0748(8) Uani d . 1 . . O
O4 -.1738(4) -.4542(3) .4137(3) .1242(14) Uani d . 1 . . O
O5 -.3094(4) -.3256(3) .3356(2) .1639(17) Uani d . 1 . . O
O6 -.0330(3) -.2902(2) .98875(18) .0801(9) Uani d . 1 . . O
O7 -.0179(2) -.3802(2) .81775(17) .0577(7) Uani d . 1 . . O
N1 .3086(3) .0690(3) .9697(2) .0488(8) Uani d . 1 . . N
H1 .348(3) .145(3) 1.0284(19) .049(10) Uiso d . 1 . . H
N2 .5408(3) .2771(3) .9928(2) .0530(8) Uani d . 1 . . N
N3 -.2118(4) -.3433(4) .4129(3) .0954(14) Uani d . 1 . . N
C1 .3793(3) .0662(3) .8842(3) .0403(9) Uani d . 1 . . C
C2 .3280(3) -.0438(3) .7976(3) .0367(8) Uani d . 1 . . C
C3 .1838(3) -.1580(4) .7874(3) .0417(9) Uani d . 1 . . C
H3 .209(2) -.245(2) .7624(17) .018(8) Uiso d . 1 . . H
C4 .1427(3) -.1573(3) .8999(3) .0388(9) Uani d . 1 . . C
C5 .2011(3) -.0458(4) .9832(3) .0410(9) Uani d . 1 . . C
C6 .5079(4) .1884(4) .9001(3) .0512(10) Uani d . 1 . . C
H6 .561(3) .202(3) .8324(19) .063(10) Uiso d . 1 . . H
C7 .6918(3) .4913(3) 1.0985(2) .0720(11) Uani d . 1 . . C
H7A .7759 .5701 1.1017 .108 Uiso calc R 1 . . H
H7B .7143 .4453 1.1666 .108 Uiso calc R 1 . . H
H7C .6050 .5261 1.0952 .108 Uiso calc R 1 . . H
C8 .4098(4) -.0570(4) .7115(3) .0477(9) Uani d . 1 . . C
C9 .4334(4) -.2175(3) .5645(3) .0938(13) Uani d . 1 . . C
H9A .3867 -.3134 .5252 .141 Uiso calc R 1 . . H
H9B .5372 -.2087 .6031 .141 Uiso calc R 1 . . H
H9C .4264 -.1512 .5090 .141 Uiso calc R 1 . . H
C10 .0574(3) -.1398(4) .6882(2) .0373(8) Uani d . 1 . . C
C11 -.0145(4) -.2463(4) .5944(3) .0464(10) Uani d . 1 . . C
H11 .024(3) -.323(3) .592(2) .041(10) Uiso d . 1 . . H
C12 -.1339(4) -.2294(4) .5107(3) .0526(10) Uani d . 1 . . C
C13 -.1847(4) -.1109(5) .5149(3) .0598(12) Uani d . 1 . . C
H13 -.268(3) -.107(3) .455(2) .068(12) Uiso d . 1 . . H
C14 -.1134(5) -.0036(5) .6053(3) .0614(12) Uani d . 1 . . C
H14 -.145(3) .078(3) .616(2) .056(11) Uiso d . 1 . . H
C15 .0070(4) -.0188(4) .6912(3) .0486(10) Uani d . 1 . . C
H15 .049(3) .060(2) .7479(18) .034(9) Uiso d . 1 . . H
C16 .0239(4) -.2786(4) .9096(3) .0496(10) Uani d . 1 . . C
C17 -.1482(4) -.5021(4) .8082(4) .0655(12) Uani d . 1 . . C
H17 -.137(3) -.535(3) .894(2) .106(13) Uiso d . 1 . . H
C18 -.1316(4) -.6212(3) .7323(3) .0929(14) Uani d . 1 . . C
H18A -.0417 -.6475 .7691 .139 Uiso calc R 1 . . H
H18B -.1256 -.5908 .6590 .139 Uiso calc R 1 . . H
H18C -.2168 -.7022 .7196 .139 Uiso calc R 1 . . H
C19 -.2868(4) -.4518(4) .7581(3) .1017(14) Uani d . 1 . . C
H19A -.2906 -.3756 .8116 .153 Uiso calc R 1 . . H
H19B -.3746 -.5301 .7455 .153 Uiso calc R 1 . . H
H19C -.2830 -.4180 .6856 .153 Uiso calc R 1 . . H
C20 .1670(3) -.0251(3) 1.0975(2) .0609(10) Uani d . 1 . . C
H20A .2276 .0660 1.1403 .091 Uiso calc R 1 . . H
H20B .1889 -.1000 1.1416 .091 Uiso calc R 1 . . H
H20C .0628 -.0280 1.0836 .091 Uiso calc R 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 .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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
N2 O1 C7 108.9(2) yes
C8 O2 C9 116.8(3) ?
C16 O7 C17 117.9(3) ?
C1 N1 C5 123.6(3) yes
C1 N1 H1 117.3(17) ?
C5 N1 H1 118.0(16) ?
C6 N2 O1 110.1(3) ?
O5 N3 O4 122.0(4) yes
O5 N3 C12 119.8(4) ?
O4 N3 C12 118.2(4) ?
C2 C1 N1 119.6(3) ?
C2 C1 C6 126.6(3) ?
N1 C1 C6 113.7(3) ?
C1 C2 C8 120.9(3) ?
C1 C2 C3 120.4(3) ?
C8 C2 C3 118.8(3) ?
C4 C3 C10 111.4(3) yes
C4 C3 C2 111.7(3) yes
C10 C3 C2 110.3(3) ?
C4 C3 H3 114.9(13) ?
C10 C3 H3 106.3(12) ?
C2 C3 H3 101.7(13) ?
C5 C4 C16 120.7(3) ?
C5 C4 C3 121.6(3) ?
C16 C4 C3 117.3(3) ?
C4 C5 N1 119.4(3) ?
C4 C5 C20 128.3(3) ?
N1 C5 C20 112.3(3) ?
N2 C6 C1 115.7(3) ?
N2 C6 H6 125.5(14) ?
C1 C6 H6 118.7(14) ?
O1 C7 H7A 109.5 ?
O1 C7 H7B 109.5 ?
H7A C7 H7B 109.5 ?
O1 C7 H7C 109.5 ?
H7A C7 H7C 109.5 ?
H7B C7 H7C 109.5 ?
O3 C8 O2 121.5(3) ?
O3 C8 C2 127.9(3) ?
O2 C8 C2 110.6(3) ?
O2 C9 H9A 109.5 ?
O2 C9 H9B 109.5 ?
H9A C9 H9B 109.5 ?
O2 C9 H9C 109.5 ?
H9A C9 H9C 109.5 ?
H9B C9 H9C 109.5 ?
C15 C10 C11 118.0(3) ?
C15 C10 C3 120.7(3) yes
C11 C10 C3 121.3(3) ?
C12 C11 C10 119.4(4) ?
C12 C11 H11 124.2(16) ?
C10 C11 H11 116.4(16) ?
C13 C12 C11 122.5(4) yes
C13 C12 N3 118.2(4) ?
C11 C12 N3 119.3(4) ?
C12 C13 C14 119.0(4) ?
C12 C13 H13 117.6(18) ?
C14 C13 H13 123.4(18) ?
C13 C14 C15 119.5(4) ?
C13 C14 H14 123.5(17) ?
C15 C14 H14 116.8(17) ?
C10 C15 C14 121.6(4) ?
C10 C15 H15 125.0(16) ?
C14 C15 H15 113.4(16) ?
O6 C16 O7 122.1(3) yes
O6 C16 C4 126.5(3) ?
O7 C16 C4 111.4(3) ?
O7 C17 C18 106.0(3) ?
O7 C17 C19 106.6(3) ?
C18 C17 C19 113.9(3) ?
O7 C17 H17 107.7(16) ?
C18 C17 H17 106.8(16) ?
C19 C17 H17 115.4(17) ?
C17 C18 H18A 109.5 ?
C17 C18 H18B 109.5 ?
H18A C18 H18B 109.5 ?
C17 C18 H18C 109.5 ?
H18A C18 H18C 109.5 ?
H18B C18 H18C 109.5 ?
C17 C19 H19A 109.5 ?
C17 C19 H19B 109.5 ?
H19A C19 H19B 109.5 ?
C17 C19 H19C 109.5 ?
H19A C19 H19C 109.5 ?
H19B C19 H19C 109.5 ?
C5 C20 H20A 109.5 ?
C5 C20 H20B 109.5 ?
H20A C20 H20B 109.5 ?
C5 C20 H20C 109.5 ?
H20A C20 H20C 109.5 ?
H20B C20 H20C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 N2 . 1.384(3) yes
O1 C7 . 1.440(3) ?
O2 C8 . 1.326(3) ?
O2 C9 . 1.450(3) ?
O3 C8 . 1.196(3) yes
O4 N3 . 1.214(4) ?
O5 N3 . 1.189(4) ?
O6 C16 . 1.214(3) yes
O7 C16 . 1.336(3) ?
O7 C17 . 1.474(4) ?
N1 C1 . 1.372(4) yes
N1 C5 . 1.376(3) yes
N1 H1 . .91(2) ?
N2 C6 . 1.280(3) ?
N3 C12 . 1.461(4) yes
C1 C2 . 1.341(3) yes
C1 C6 . 1.453(4) ?
C2 C8 . 1.467(4) ?
C2 C3 . 1.521(4) yes
C3 C4 . 1.505(4) yes
C3 C10 . 1.515(4) yes
C3 H3 . .980(19) ?
C4 C5 . 1.326(4) yes
C4 C16 . 1.465(4) ?
C5 C20 . 1.505(3) ?
C6 H6 . 1.07(2) ?
C7 H7A . .9600 ?
C7 H7B . .9600 ?
C7 H7C . .9600 ?
C9 H9A . .9600 ?
C9 H9B . .9600 ?
C9 H9C . .9600 ?
C10 C15 . 1.372(4) ?
C10 C11 . 1.383(4) ?
C11 C12 . 1.363(4) ?
C11 H11 . .91(2) ?
C12 C13 . 1.352(4) ?
C13 C14 . 1.361(5) ?
C13 H13 . .93(2) ?
C14 C15 . 1.377(4) ?
C14 H14 . .92(2) ?
C15 H15 . .92(2) ?
C17 C18 . 1.486(4) ?
C17 C19 . 1.512(4) ?
C17 H17 . 1.09(3) ?
C18 H18A . .9600 ?
C18 H18B . .9600 ?
C18 H18C . .9600 ?
C19 H19A . .9600 ?
C19 H19B . .9600 ?
C19 H19C . .9600 ?
C20 H20A . .9600 ?
C20 H20B . .9600 ?
C20 H20C . .9600 ?
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
C7 O1 N2 C6 177.1(3) ?
C5 N1 C1 C2 10.7(5) yes
C5 N1 C1 C6 -168.7(3) ?
N1 C1 C2 C8 -173.9(3) ?
C6 C1 C2 C8 5.4(5) ?
N1 C1 C2 C3 5.8(4) ?
C6 C1 C2 C3 -174.9(3) ?
C1 C2 C3 C4 -18.6(4) yes
C8 C2 C3 C4 161.0(3) ?
C1 C2 C3 C10 105.9(3) ?
C8 C2 C3 C10 -74.4(4) ?
C10 C3 C4 C5 -106.1(3) ?
C2 C3 C4 C5 17.8(4) yes
C10 C3 C4 C16 67.7(4) ?
C2 C3 C4 C16 -168.4(3) ?
C16 C4 C5 N1 -177.5(3) ?
C3 C4 C5 N1 -3.9(5) ?
C16 C4 C5 C20 3.2(5) ?
C3 C4 C5 C20 176.9(3) ?
C1 N1 C5 C4 -11.8(4) yes
C1 N1 C5 C20 167.6(3) ?
O1 N2 C6 C1 -178.6(2) ?
C2 C1 C6 N2 -176.5(3) ?
N1 C1 C6 N2 2.9(4) ?
C9 O2 C8 O3 3.8(5) ?
C9 O2 C8 C2 -176.9(3) ?
C1 C2 C8 O3 -13.8(5) yes
C3 C2 C8 O3 166.6(3) ?
C1 C2 C8 O2 167.1(3) yes
C3 C2 C8 O2 -12.6(4) ?
C4 C3 C10 C15 60.9(4) yes
C2 C3 C10 C15 -63.8(4) yes
C4 C3 C10 C11 -116.5(3) ?
C2 C3 C10 C11 118.8(3) ?
C15 C10 C11 C12 -1.7(4) ?
C3 C10 C11 C12 175.8(3) ?
C10 C11 C12 C13 .7(5) ?
C10 C11 C12 N3 -178.8(3) ?
O5 N3 C12 C13 5.5(6) ?
O4 N3 C12 C13 -174.3(4) ?
O5 N3 C12 C11 -175.0(4) ?
O4 N3 C12 C11 5.2(6) yes
C11 C12 C13 C14 .6(5) ?
N3 C12 C13 C14 -179.9(3) ?
C12 C13 C14 C15 -1.0(5) ?
C11 C10 C15 C14 1.3(5) ?
C3 C10 C15 C14 -176.2(3) ?
C13 C14 C15 C10 .0(5) ?
C17 O7 C16 O6 6.5(5) ?
C17 O7 C16 C4 -173.3(3) ?
C5 C4 C16 O6 1.0(5) yes
C3 C4 C16 O6 -173.0(3) ?
C5 C4 C16 O7 -179.2(3) yes
C3 C4 C16 O7 6.9(4) ?
C16 O7 C17 C18 -157.2(3) ?
C16 O7 C17 C19 81.1(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21376812
