data_2011414
_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  'C21 H27 N O6'
_chemical_formula_sum  'C21 H27 N O6'
_chemical_formula_weight  389.4
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/c'
loop_
_symmetry_equiv_pos_as_xyz
  'x,y,z'
  '-x,-y,-z'
  '-x,1/2+y, 1/2-z'
  'x,1/2-y,1/2+z'
_cell_length_a  8.268(4)
_cell_length_b  17.802(7)
_cell_length_c  14.707(8)
_cell_angle_alpha  90.0
_cell_angle_beta  93.32(2)
_cell_angle_gamma  90.0
_cell_volume  2161(2)
_cell_formula_units_Z  4
_cell_measurement_temperature  301
_exptl_crystal_density_diffrn  1.196
_exptl_crystal_density_meas  'not meas'
_exptl_Crystal_F_000  832
_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  .0502(3)  .25955(13)  .02486(12)  .0601(6) Uani d . 1 . . N
  H1A  .0206  .2473  -.0424  .080 Uiso d R 1 . . H
  C2  -.0537(3)  .23768(13)  .09114(15)  .0515(6) Uani d . 1 . . C
  C2'  -.2016(4)  .19576(16)  .05191(18)  .0693(8) Uani d . 1 . . C
  H2'A  -.2690  .1822  .1003  .080 Uiso d PR  .50 . . H
  H2'B  -.2614  .2275  .0092  .080 Uiso d PR  .50 . . H
  H2'C  -.1680  .1512  .0215  .080 Uiso d PR  .50 . . H
  H2'D  -.1918  .1965  -.0128  .050 Uiso d PR  .50 . . H
  H2'E  -.2995  .2219  .0643  .050 Uiso d PR  .50 . . H
  H2'F  -.2076  .1442  .0706  .050 Uiso d PR  .50 . . H
  C3  -.0146(3)  .25492(13)  .18020(14)  .0477(5) Uani d . 1 . . C
  C3'  -.1065(3)  .23082(14)  .25803(16)  .0554(6) Uani d . 1 . . C
  C3"  -.3273(5)  .1594(2)  .3119(2)  .1092(14) Uani d . 1 . . C
  H3"A  -.2574  .1337  .3560  .080 Uiso d R 1 . . H
  H3"B  -.3763  .2011  .3412  .080 Uiso d R 1 . . H
  C3"'  -.4483(7)  .1076(3)  .2788(4)  .199(3) Uani d . 1 . . C
  H3"C  -.5119  .0890  .3265  .080 Uiso d R 1 . . H
  H3"D  -.5172  .1341  .2348  .080 Uiso d R 1 . . H
  H3"E  -.3976  .0662  .2497  .080 Uiso d R 1 . . H
  O3'  -.0726(3)  .25036(13)  .33577(11)  .0842(7) Uani d . 1 . . O
  O3"  -.2334(2)  .18531(11)  .23730(12)  .0770(6) Uani d . 1 . . O
  C4  .1257(3)  .30926(13)  .20576(15)  .0503(6) Uani d . 1 . . C
  H4A  .1786  .2921  .2618  .080 Uiso d R 1 . . H
  C5  .2504(3)  .30841(14)  .13140(16)  .0528(6) Uani d . 1 . . C
  C5'  .4153(3)  .33755(16)  .1544(2)  .0668(7) Uani d . 1 . . C
  C5"  .5923(4)  .3919(2)  .2716(3)  .1061(13) Uani d . 1 . . C
  H5"A  .6775  .3554  .2698  .080 Uiso d R 1 . . H
  H5"B  .6150  .4321  .2308  .080 Uiso d R 1 . . H
  C5"'  .5894(5)  .4203(3)  .3612(3)  .1279(16) Uani d . 1 . . C
  H5"C  .6906  .4433  .3806  .080 Uiso d R 1 . . H
  H5"D  .5042  .4568  .3622  .080 Uiso d R 1 . . H
  H5"E  .5671  .3796  .4015  .080 Uiso d R 1 . . H
  O5'  .5241(3)  .34555(16)  .10227(17)  .1087(9) Uani d . 1 . . O
  O5"  .4371(2)  .35684(13)  .24239(14)  .0830(6) Uani d . 1 . . O
  C6  .2061(3)  .28745(14)  .04484(16)  .0566(7) Uani d . 1 . . C
  C6'  .3090(4)  .28941(17)  -.03778(19)  .0732(8) Uani d . 1 . . C
  H6'A  .4146  .3090  -.0207  .080 Uiso d PR  .50 . . H
  H6'B  .3191  .2394  -.0612  .080 Uiso d PR  .50 . . H
  H6'C  .2573  .3209  -.0838  .080 Uiso d PR  .50 . . H
  H6'D  .2152  .2776  -.0767  .050 Uiso d PR  .50 . . H
  H6'E  .3396  .3401  -.0508  .050 Uiso d PR  .50 . . H
  H6'F  .4033  .2595  -.0225  .050 Uiso d PR  .50 . . H
  C7  .0613(3)  .38914(14)  .22152(17)  .0560(6) Uani d . 1 . . C
  C8  .0863(4)  .42771(17)  .30437(19)  .0694(8) Uani d . 1 . . C
  C9  .0245(4)  .50103(19)  .3121(2)  .0864(10) Uani d . 1 . . C
  H9A  .0458  .5280  .3681  .080 Uiso d R 1 . . H
  C10  -.0623(4)  .53421(18)  .2403(3)  .0889(10) Uani d . 1 . . C
  H10A  -.1050  .5839  .2470  .080 Uiso d R 1 . . H
  C11  -.0916(4)  .49695(17)  .1582(2)  .0751(8) Uani d . 1 . . C
  C12  -.0276(3)  .42476(14)  .14968(19)  .0622(7) Uani d . 1 . . C
  H12A  -.0468  .3984  .0931  .080 Uiso d R 1 . . H
  O8  .1708(3)  .38995(13)  .37481(13)  .0875(7) Uani d . 1 . . O
  C8'  .1824(5)  .4239(2)  .4625(2)  .1115(13) Uani d . 1 . . C
  H8'A  .2432  .3917  .5042  .080 Uiso d R 1 . . H
  H8'B  .2377  .4710  .4578  .080 Uiso d R 1 . . H
  H8'C  .0768  .4324  .4844  .080 Uiso d R 1 . . H
  O11  -.1821(3)  .53461(13)  .0910(2)  .1055(8) Uani d . 1 . . O
  C11'  -.2442(4)  .4926(2)  .0141(3)  .0987(11) Uani d . 1 . . C
  H11A  -.3048  .5241  -.0286  .080 Uiso d R 1 . . H
  H11B  -.1546  .4707  -.0151  .080 Uiso d R 1 . . H
  H11C  -.3130  .4535  .0348  .080 Uiso d R 1 . . 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  .0707(15)  .0751(14)  .0351(10)  -.0010(12)  .0086(9)  -.0001(9)
  C2  .0617(15)  .0529(13)  .0400(11)  .0012(12)  .0037(11)  -.0022(10)
  C2'  .0802(19)  .0778(18)  .0493(14)  -.0072(16)  -.0019(13)  -.0103(13)
  C3  .0551(14)  .0491(13)  .0392(11)  .0005(11)  .0059(10)  .0000(10)
  C3'  .0616(15)  .0591(14)  .0458(13)  -.0030(13)  .0074(11)  .0019(11)
  C3"  .121(3)  .118(3)  .093(3)  -.048(3)  .054(2)  -.004(2)
  C3"'  .213(6)  .224(6)  .174(5)  -.143(5)  .117(5)  -.082(5)
  O3'  .0968(15)  .1200(17)  .0367(9)  -.0301(13)  .0108(9)  -.0027(10)
  O3"  .0840(14)  .0870(13)  .0617(11)  -.0296(12)  .0199(10)  -.0050(10)
  C4  .0572(14)  .0535(13)  .0406(11)  -.0021(12)  .0066(10)  -.0028(10)
  C5  .0564(15)  .0525(13)  .0505(13)  .0043(12)  .0125(11)  .0018(11)
  C5'  .0547(16)  .0646(17)  .083(2)  .0038(14)  .0174(15)  -.0007(15)
  C5"  .057(2)  .125(3)  .136(3)  -.017(2)  .000(2)  -.024(3)
  C5"'  .103(3)  .154(4)  .121(3)  -.038(3)  -.041(3)  .010(3)
  O5'  .0720(14)  .143(2)  .1147(19)  -.0240(14)  .0397(14)  -.0227(16)
  O5"  .0558(12)  .1123(17)  .0809(14)  -.0112(11)  .0037(10)  -.0149(12)
  C6  .0650(17)  .0540(14)  .0525(14)  .0096(13)  .0192(12)  .0046(11)
  C6'  .080(2)  .0795(19)  .0629(16)  .0051(16)  .0262(14)  .0035(14)
  C7  .0561(15)  .0574(14)  .0564(14)  -.0053(12)  .0186(12)  -.0089(12)
  C8  .0697(18)  .0727(19)  .0672(17)  -.0087(15)  .0157(15)  -.0226(15)
  C9  .089(2)  .078(2)  .094(2)  -.0130(19)  .0243(19)  -.0378(19)
  C10  .092(2)  .0565(18)  .122(3)  -.0019(17)  .035(2)  -.0203(19)
  C11  .077(2)  .0584(17)  .092(2)  .0017(16)  .0230(17)  .0060(16)
  C12  .0657(17)  .0531(15)  .0696(17)  .0001(13)  .0189(14)  -.0006(13)
  O8  .0969(16)  .1005(16)  .0645(13)  .0005(13)  -.0007(11)  -.0310(12)
  C8'  .149(3)  .115(3)  .071(2)  -.010(3)  .006(2)  -.034(2)
  O11  .124(2)  .0677(14)  .125(2)  .0242(14)  .0088(17)  .0129(14)
  C11'  .090(2)  .091(2)  .115(3)  .015(2)  .016(2)  .040(2)
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 . 1.392(3) ?
  N1 C6 . 1.397(3) ?
  N1 H1A . 1.0282 ?
  C2 C3 . 1.366(3) ?
  C2 C2' . 1.517(4) ?
  C2' H2'A .  .9600 ?
  C2' H2'B .  .9600 ?
  C2' H2'C .  .9600 ?
  C2' H2'D .  .9600 ?
  C2' H2'E .  .9600 ?
  C2' H2'F .  .9600 ?
  C3 C3' . 1.474(3) ?
  C3 C4 . 1.540(3) ?
  C3' O3' . 1.212(3) ?
  C3' O3" . 1.347(3) ?
  C3" C3"' . 1.426(5) ?
  C3" O3" . 1.455(3) ?
  C3" H3"A .  .9600 ?
  C3" H3"B .  .9599 ?
  C3"' H3"C .  .9600 ?
  C3"' H3"D .  .9599 ?
  C3"' H3"E .  .9601 ?
  C4 C7 . 1.541(3) ?
  C4 C5 . 1.546(3) ?
  C4 H4A .  .9600 ?
  C5 C6 . 1.356(3) ?
  C5 C5' . 1.480(4) ?
  C5' O5' . 1.224(3) ?
  C5' O5" . 1.340(3) ?
  C5" C5"' . 1.412(5) ?
  C5" O5" . 1.469(4) ?
  C5" H5"A .  .9600 ?
  C5" H5"B .  .9600 ?
  C5"' H5"C .  .9600 ?
  C5"' H5"D .  .9600 ?
  C5"' H5"E .  .9600 ?
  C6 C6' . 1.523(3) ?
  C6' H6'A .  .9600 ?
  C6' H6'B .  .9599 ?
  C6' H6'C .  .9601 ?
  C6' H6'D .  .9600 ?
  C6' H6'E .  .9600 ?
  C6' H6'F .  .9600 ?
  C7 C12 . 1.403(4) ?
  C7 C8 . 1.403(4) ?
  C8 O8 . 1.389(4) ?
  C8 C9 . 1.409(5) ?
  C9 C10 . 1.375(5) ?
  C9 H9A .  .9600 ?
  C10 C11 . 1.387(4) ?
  C10 H10A .  .9600 ?
  C11 O11 . 1.379(4) ?
  C11 C12 . 1.398(4) ?
  C12 H12A .  .9600 ?
  O8 C8' . 1.423(3) ?
  C8' H8'A .  .9599 ?
  C8' H8'B .  .9600 ?
  C8' H8'C .  .9600 ?
  O11 C11' . 1.427(4) ?
  C11' H11A .  .9599 ?
  C11' H11B .  .9600 ?
  C11' H11C .  .9600 ?