data_2011416
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2000
_journal_volume  56
_journal_page_first  1228
_journal_page_last  1231
_publ_section_title
;
Three methoxy-substituted
diethyl 4-phenyl-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate compounds
;
loop_
_publ_author_name
  'Sara K. Metcalf'
  'Elizabeth M. Holt'
_chemical_formula_moiety  'C22 H29 N1 O7'
_chemical_formula_sum  'C22 H29 N1 O7'
_chemical_formula_weight  419.46
_symmetry_cell_setting  orthorhombic
_symmetry_space_group_name_H-M  'P 21 21 21'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, -y, z+1/2'
  '-x, y+1/2, -z+1/2'
  'x+1/2, -y+1/2, -z'
_cell_length_a  8.714(8)
_cell_length_b  16.167(14)
_cell_length_c  16.948(14)
_cell_angle_alpha  90.0
_cell_angle_beta  90.0
_cell_angle_gamma  90.0
_cell_volume  2388(5)
_cell_formula_units_Z  4
_cell_measurement_temperature  301
_exptl_crystal_density_diffrn  1.164
_diffrn_ambient_temperature  298
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
  N1  .1083(4)  .22006(19)  .15745(19)  .0613(9) Uani d . 1 . . N
  H1A  .0601  .2510  .1940  .080 Uiso d R 1 . . H
  C2  .0294(5)  .1999(2)  .0891(2)  .0566(9) Uani d . 1 . . C
  C2'  -.1108(7)  .2544(3)  .0738(3)  .0850(15) Uani d . 1 . . C
  H2'A  -.1592  .2372  .0267  .080 Uiso d PR  .50 . . H
  H2'B  -.1826  .2474  .1179  .080 Uiso d PR  .50 . . H
  H2'C  -.0827  .3115  .0713  .080 Uiso d PR  .50 . . H
  H2'D  -.2038  .2219  .0747  .080 Uiso d PR  .50 . . H
  H2'E  -.1502  .2879  .0328  .080 Uiso d PR  .50 . . H
  H2'F  -.1580  .2930  .1109  .080 Uiso d PR  .50 . . H
  C3  .0838(5)  .1376(2)  .0422(2)  .0504(8) Uani d . 1 . . C
  C3'  .0101(6)  .1181(3)  -.0353(2)  .0644(11) Uani d . 1 . . C
  C3"  .0401(10)  .0372(5)  -.1528(4)  .124(2) Uani d D 1 . . C
  H3"H  .1157  .0431  -.1936  .080 Uiso d PR  .50 . . H
  H3"G  .0396  -.0221  -.1564  .080 Uiso d PR  .50 . . H
  H3  -.0545  .0629  -.1682  .080 Uiso d R 1 . . H
  O3'  -.1156(5)  .1403(3)  -.0585(2)  .1045(13) Uani d . 1 . . O
  O3"  .0992(5)  .0675(2)  -.07832(18)  .0958(11) Uani d . 1 . . O
  C4  .2261(4)  .08673(19)  .06655(19)  .0452(8) Uani d . 1 . . C
  H4A  .2893  .0789  .0208  .080 Uiso d R 1 . . H
  C5  .3225(4)  .1320(2)  .1287(2)  .0500(8) Uani d . 1 . . C
  C5'  .4858(5)  .1071(3)  .1386(3)  .0666(11) Uani d . 1 . . C
  C5"  .6881(6)  .0167(4)  .0925(4)  .0989(18) Uani d . 1 . . C
  H5"A  .7063  -.0048  .1444  .080 Uiso d R 1 . . H
  H5"B  .7597  .0607  .0826  .080 Uiso d R 1 . . H
  C5'"  .7070(9)  -.0516(4)  .0372(6)  .150(3) Uani d . 1 . . C
  H5'A  .8093  -.0735  .0395  .080 Uiso d R 1 . . H
  H5'B  .6346  -.0950  .0477  .080 Uiso d R 1 . . H
  H5'C  .6882  -.0292  -.0144  .080 Uiso d R 1 . . H
  O5'  .5794(4)  .1333(4)  .1862(3)  .1304(18) Uani d . 1 . . O
  O5"  .5289(3)  .04798(19)  .0863(2)  .0781(9) Uani d . 1 . . O
  C6  .2593(5)  .1931(2)  .1733(2)  .0553(9) Uani d . 1 . . C
  C6'  .3350(7)  .2394(3)  .2407(3)  .0838(14) Uani d . 1 . . C
  H6'A  .4339  .2199  .2473  .080 Uiso d PR  .50 . . H
  H6'B  .3359  .2991  .2299  .080 Uiso d PR  .50 . . H
  H6'C  .2742  .2318  .2884  .080 Uiso d PR  .50 . . H
  H6'D  .2558  .2751  .2659  .080 Uiso d PR  .50 . . H
  H6'E  .3795  .2016  .2755  .080 Uiso d PR  .50 . . H
  H6'F  .4343  .2601  .2318  .080 Uiso d PR  .50 . . H
  C7  .1772(4)  -.00111(19)  .09624(19)  .0435(7) Uani d . 1 . . C
  C8  .0944(5)  -.0109(2)  .1662(2)  .0494(8) Uani d . 1 . . C
  H8A  .0647  .0370  .1961  .080 Uiso d R 1 . . H
  C9  .0545(5)  -.0904(2)  .1927(2)  .0523(9) Uani d . 1 . . C
  C10  .0975(4)  -.16046(19)  .1482(2)  .0477(8) Uani d . 1 . . C
  C11  .1787(4)  -.1505(2)  .0778(2)  .0512(8) Uani d . 1 . . C
  C12  .2196(5)  -.0706(2)  .0525(2)  .0519(9) Uani d . 1 . . C
  H12A  .2757  -.0636  .0042  .080 Uiso d R 1 . . H
  C13  -.0673(8)  -.0401(3)  .3117(3)  .097(2) Uani d . 1 . . C
  H13A  -.1204  -.0602  .3575  .080 Uiso d R 1 . . H
  H13B  .0233  -.0108  .3279  .080 Uiso d R 1 . . H
  H13C  -.1332  -.0034  .2828  .080 Uiso d R 1 . . H
  C14  .1761(8)  -.2929(3)  .1968(4)  .0940(17) Uani d . 1 . . C
  H14A  .1393  -.3454  .2153  .080 Uiso d R 1 . . H
  H14B  .2408  -.3012  .1517  .080 Uiso d R 1 . . H
  H14C  .2338  -.2663  .2379  .080 Uiso d R 1 . . H
  C15  .3164(10)  -.2180(3)  -.0280(4)  .124(3) Uani d . 1 . . C
  H15A  .3296  -.2719  -.0507  .080 Uiso d R 1 . . H
  H15B  .2736  -.1813  -.0668  .080 Uiso d R 1 . . H
  H15C  .4141  -.1971  -.0110  .080 Uiso d R 1 . . H
  O9  -.0234(5)  -.10739(17)  .26251(17)  .0781(10) Uani d . 1 . . O
  O10  .0533(3)  -.23849(14)  .17638(17)  .0630(8) Uani d . 1 . . O
  O11  .2118(4)  -.22208(15)  .03702(17)  .0723(9) Uani d . 1 . . O
  C3"B  .111(3)  .0802(12)  -.2168(10)  .184(8) Uiso d PD  .50 . . C
  H3"D  .0846  .0691  -.2707  .080 Uiso d PR  .50 . . H
  H3"E  .1005  .1383  -.2065  .080 Uiso d PR  .50 . . H
  H3"F  .2154  .0637  -.2074  .080 Uiso d PR  .50 . . H
  C3"A  -.003(3)  -.0481(6)  -.1502(12)  .181(8) Uiso d PD  .50 . . C
  H3"A  -.0426  -.0592  -.2020  .080 Uiso d PR  .50 . . H
  H3"B  .0778  -.0864  -.1383  .080 Uiso d PR  .50 . . H
  H3"C  -.0839  -.0540  -.1121  .080 Uiso d PR  .50 . . 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  .075(2)  .0504(16)  .0582(17)  .0106(17)  -.0003(18)  -.0082(14)
  C2  .068(2)  .0448(16)  .0570(19)  .0055(18)  -.002(2)  .0069(16)
  C2'  .097(4)  .067(3)  .091(3)  .036(3)  -.021(3)  .000(2)
  C3  .060(2)  .0432(16)  .0478(17)  -.0002(17)  -.0025(17)  .0104(14)
  C3'  .075(3)  .060(2)  .058(2)  .005(2)  -.012(2)  .0084(18)
  C3"  .137(6)  .153(6)  .082(3)  .017(5)  -.036(4)  -.016(4)
  O3'  .101(3)  .125(3)  .087(2)  .029(3)  -.036(2)  -.006(2)
  O3"  .109(3)  .116(3)  .0619(16)  .023(3)  -.0265(19)  -.0273(18)
  C4  .0506(19)  .0398(15)  .0451(16)  -.0037(15)  .0046(16)  .0040(13)
  C5  .054(2)  .0451(16)  .0510(18)  -.0099(17)  .0001(17)  .0045(15)
  C5'  .052(2)  .075(3)  .073(2)  -.009(2)  .002(2)  -.011(2)
  C5"  .054(3)  .116(4)  .127(5)  .015(3)  .004(3)  -.007(4)
  C5'"  .087(4)  .104(5)  .258(10)  .034(4)  -.022(6)  -.026(6)
  O5'  .068(2)  .182(4)  .142(3)  .010(3)  -.037(2)  -.079(3)
  O5"  .0499(15)  .0785(18)  .106(2)  .0039(15)  -.0024(18)  -.0224(19)
  C6  .069(2)  .0448(16)  .0523(18)  -.0052(18)  .001(2)  -.0020(16)
  C6'  .087(3)  .078(3)  .086(3)  -.005(3)  -.009(3)  -.027(3)
  C7  .0452(17)  .0406(15)  .0447(16)  -.0012(15)  -.0049(15)  .0045(14)
  C8  .058(2)  .0366(14)  .0531(18)  .0016(16)  .0090(18)  .0033(14)
  C9  .059(2)  .0457(17)  .0527(18)  .0023(16)  .0101(18)  .0074(15)
  C10  .0528(19)  .0347(14)  .0556(18)  -.0019(15)  -.0019(18)  .0059(14)
  C11  .057(2)  .0413(16)  .0556(19)  .0010(17)  -.0008(19)  -.0019(15)
  C12  .058(2)  .0441(16)  .0535(18)  -.0024(17)  .0073(18)  -.0011(15)
  C13  .143(5)  .065(2)  .084(3)  -.008(3)  .058(4)  .004(2)
  C14  .115(4)  .057(2)  .110(4)  .024(3)  .003(4)  .024(3)
  C15  .165(7)  .063(3)  .144(5)  -.007(4)  .070(5)  -.031(3)
  O9  .113(3)  .0516(14)  .0700(16)  -.0042(18)  .0398(18)  .0077(13)
  O10  .0708(18)  .0418(12)  .0763(17)  -.0025(13)  -.0022(16)  .0098(12)
  O11  .095(2)  .0445(13)  .0771(17)  -.0031(16)  .0222(18)  -.0144(13)
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
  N1 C2 . 1.386(5) ?
  N1 C6 . 1.412(6) ?
  C2 C3 . 1.368(5) ?
  C2 C2' . 1.528(6) ?
  C3 C3' . 1.494(6) ?
  C3 C4 . 1.544(5) ?
  C3' O3' . 1.218(6) ?
  C3' O3" . 1.344(6) ?
  C3" C3"A . 1.4297(15) ?
  C3" C3"B . 1.4298(13) ?
  C3" O3" . 1.448(7) ?
  C4 C5 . 1.534(5) ?
  C4 C7 . 1.566(4) ?
  C5 C6 . 1.359(5) ?
  C5 C5' . 1.488(6) ?
  C5' O5' . 1.223(5) ?
  C5' O5" . 1.358(5) ?
  C5" C5'" . 1.457(10) ?
  C5" O5" . 1.480(6) ?
  C6 C6' . 1.516(6) ?
  C7 C12 . 1.395(5) ?
  C7 C8 . 1.397(5) ?
  C8 C9 . 1.405(5) ?
  C9 O9 . 1.391(4) ?
  C9 C10 . 1.412(5) ?
  C10 C11 . 1.396(5) ?
  C10 O10 . 1.403(4) ?
  C11 O11 . 1.378(4) ?
  C11 C12 . 1.408(5) ?
  C13 O9 . 1.424(5) ?
  C14 O10 . 1.428(6) ?
  C15 O11 . 1.432(7) ?