#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2011416.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_2011416
loop_
_publ_author_name
'Metcalf, Sara K.'
'Holt, Elizabeth M.'
_publ_section_title
;
 Three methoxy-substituted diethyl
 4-phenyl-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate compounds
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1228
_journal_page_last               1231
_journal_volume                  56
_journal_year                    2000
_chemical_formula_moiety         'C22 H29 N1 O7'
_chemical_formula_sum            'C22 H29 N O7'
_chemical_formula_weight         419.46
_chemical_name_systematic
;
4-(3,4,5-trimethoxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-bis(ethoxyca
rbonyl) (III)
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   8.714(8)
_cell_length_b                   16.167(14)
_cell_length_c                   16.948(14)
_cell_measurement_reflns_used    46
_cell_measurement_temperature    301
_cell_measurement_theta_max      12.84
_cell_measurement_theta_min      4.08
_cell_volume                     2388(4)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1991)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    'XP (Siemens, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXS97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full .994
_diffrn_measured_fraction_theta_max .994
_diffrn_measurement_device_type  'Syntex 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     .71073
_diffrn_reflns_av_R_equivalents  .041
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            4844
_diffrn_reflns_theta_full        30.03
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         2.4
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_time  '97 reflections'
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .087
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_density_meas      'not meas'
_exptl_crystal_description       rhomb
_exptl_crystal_F_000             892
_exptl_crystal_size_max          .3
_exptl_crystal_size_mid          .2
_exptl_crystal_size_min          .2
_refine_diff_density_max         .34
_refine_diff_density_min         -.28
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.00
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     270
_refine_ls_number_reflns         4634
_refine_ls_R_factor_all          .125
_refine_ls_R_factor_gt           .069
_refine_ls_shift/su_max          .045
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.1102P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_ref         .220
_reflns_number_gt                2616
_reflns_number_total             4634
_reflns_threshold_expression     I<2\s(I)
_[local]_cod_data_source_file    fr1251.cif
_[local]_cod_data_source_block   III
_[local]_cod_cif_authors_sg_H-M  'P21 21 21'
_[local]_cod_chemical_formula_sum_orig 'C22 H29 N1 O7'
_cod_original_cell_volume        2388(5)
_cod_database_code               2011416
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'
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_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_
_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
C2 N1 C6 123.3(3)
C3 C2 N1 119.1(4)
C3 C2 C2' 127.1(4)
N1 C2 C2' 113.8(3)
C2 C3 C3' 121.1(4)
C2 C3 C4 121.0(3)
C3' C3 C4 117.9(3)
O3' C3' O3" 121.6(4)
O3' C3' C3 127.4(4)
O3" C3' C3 110.9(4)
C3"A C3" C3"B 127.4(14)
C3"A C3" O3" 113.1(10)
C3"B C3" O3" 110.0(11)
C3' O3" C3" 118.3(5)
C5 C4 C3 111.7(3)
C5 C4 C7 111.2(3)
C3 C4 C7 110.5(3)
C6 C5 C5' 121.4(4)
C6 C5 C4 120.4(3)
C5' C5 C4 118.1(3)
O5' C5' O5" 119.4(4)
O5' C5' C5 128.2(4)
O5" C5' C5 112.5(4)
C5'" C5" O5" 108.6(5)
C5' O5" C5" 117.0(4)
C5 C6 N1 119.8(3)
C5 C6 C6' 126.9(4)
N1 C6 C6' 113.3(4)
C12 C7 C8 119.8(3)
C12 C7 C4 119.2(3)
C8 C7 C4 121.1(3)
C7 C8 C9 120.2(3)
O9 C9 C8 125.0(3)
O9 C9 C10 115.1(3)
C8 C9 C10 119.8(3)
C11 C10 O10 122.2(3)
C11 C10 C9 119.9(3)
O10 C10 C9 117.9(3)
O11 C11 C10 116.0(3)
O11 C11 C12 124.4(3)
C10 C11 C12 119.6(3)
C7 C12 C11 120.7(3)
C9 O9 C13 118.6(3)
C10 O10 C14 115.5(3)
C11 O11 C15 118.7(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
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)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1A O10 3 .90 2.42 3.219(5) 148.9 no
N1 H1A O9 3 .90 2.42 3.189(5) 142.6 no