#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/05/2210587.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_2210587
loop_
_publ_author_name
'Sun, Feng-Xia'
'Zhao, Ying'
'Zhang, Cui'
'Zhang, Yan-Hui'
_publ_section_title
;
 3-(2-Acetoxyethyl) 5-methyl
 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
;
_journal_coeditor_code           EZ2035
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4763
_journal_page_last               o4764
_journal_paper_doi               10.1107/S1600536806039328
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C20 H22 N2 O8'
_chemical_formula_moiety         'C20 H22 N2 O8'
_chemical_formula_sum            'C20 H22 N2 O8'
_chemical_formula_weight         418.40
_chemical_melting_point          .395E-305
_chemical_name_systematic
;
3-(2-Acetoxyethyl) 5-methyl
2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                93.452(6)
_cell_angle_beta                 90.871(5)
_cell_angle_gamma                109.153(6)
_cell_formula_units_Z            2
_cell_length_a                   9.0389(12)
_cell_length_b                   10.6990(14)
_cell_length_c                   11.0049(16)
_cell_measurement_reflns_used    2795
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      1.9
_cell_volume                     1002.8(2)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'CrystalStructure (Rigaku/MSC, 2005)'
_computing_publication_material  CrystalStructure
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.032
_diffrn_reflns_av_sigmaI/netI    0.045
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12582
_diffrn_reflns_theta_full        27.8
_diffrn_reflns_theta_max         27.8
_diffrn_reflns_theta_min         1.9
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Jacobson, 1998)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.42
_refine_diff_density_min         -0.25
_refine_ls_extinction_coef       0.032(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4730
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.06
_refine_ls_R_factor_all          0.052
_refine_ls_R_factor_gt           0.038
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0614P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.102
_refine_ls_wR_factor_ref         0.109
_reflns_number_gt                3265
_reflns_number_total             4730
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ez2035.cif
_cod_data_source_block           I
_cod_database_code               2210587
_cod_database_fobs_code          2210587
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_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
N N1 0.61445(13) 0.35044(11) 0.51127(10) 0.0209(3) Uani d . 1
N N2 0.87217(13) 0.05081(11) 0.20759(10) 0.0237(3) Uani d . 1
O O1 0.89988(10) 0.65892(9) 0.23939(8) 0.0234(2) Uani d . 1
O O2 0.96634(10) 0.70536(9) 0.43856(8) 0.0229(2) Uani d . 1
O O3 0.23864(11) 0.21212(10) 0.24227(9) 0.0299(3) Uani d . 1
O O4 0.41697(10) 0.31821(9) 0.11045(8) 0.0228(2) Uani d . 1
O O5 0.44754(10) 0.15281(9) -0.09725(8) 0.0228(2) Uani d . 1
O O6 0.59419(12) 0.22874(10) -0.25596(9) 0.0339(3) Uani d . 1
O O7 0.81843(13) 0.01321(10) 0.30607(9) 0.0369(3) Uani d . 1
O O8 0.94119(11) -0.00877(10) 0.14291(9) 0.0300(2) Uani d . 1
C C1 0.74001(14) 0.46311(12) 0.49198(11) 0.0179(3) Uani d . 1
C C2 0.76028(14) 0.50605(12) 0.37798(11) 0.0166(3) Uani d . 1
C C3 0.65861(14) 0.42511(12) 0.26960(11) 0.0162(3) Uani d . 1
H H3 0.6337 0.4888 0.2165 0.019 Uiso calc R 1
C C4 0.50394(14) 0.33286(12) 0.31271(11) 0.0181(3) Uani d . 1
C C5 0.49087(15) 0.29385(13) 0.42789(12) 0.0198(3) Uani d . 1
C C6 0.83640(15) 0.52361(13) 0.60628(11) 0.0225(3) Uani d . 1
H H6A 0.9479 0.5448 0.5898 0.034 Uiso calc R 1
H H6B 0.8086 0.4605 0.6699 0.034 Uiso calc R 1
H H6C 0.8156 0.6049 0.6336 0.034 Uiso calc R 1
C C7 0.88031(14) 0.62832(13) 0.34424(11) 0.0174(3) Uani d . 1
C C8 1.08140(16) 0.82885(14) 0.40680(13) 0.0293(3) Uani d . 1
H H8A 1.1600 0.8093 0.3557 0.044 Uiso calc R 1
H H8B 1.1328 0.8807 0.4813 0.044 Uiso calc R 1
H H8C 1.0289 0.8798 0.3620 0.044 Uiso calc R 1
C C9 0.74544(14) 0.34905(12) 0.19278(11) 0.0169(3) Uani d . 1
C C10 0.77475(14) 0.23966(12) 0.23651(11) 0.0172(3) Uani d . 1
H H10 0.7447 0.2130 0.3158 0.021 Uiso calc R 1
C C11 0.84864(14) 0.16992(12) 0.16250(11) 0.0188(3) Uani d . 1
C C12 0.89591(14) 0.20521(13) 0.04708(11) 0.0214(3) Uani d . 1
H H12 0.9449 0.1551 -0.0019 0.026 Uiso calc R 1
C C13 0.86977(15) 0.31590(14) 0.00468(12) 0.0244(3) Uani d . 1
H H13 0.9033 0.3439 -0.0736 0.029 Uiso calc R 1
C C14 0.79441(15) 0.38603(14) 0.07686(12) 0.0217(3) Uani d . 1
H H14 0.7759 0.4610 0.0463 0.026 Uiso calc R 1
C C15 0.37173(15) 0.28022(13) 0.22326(12) 0.0198(3) Uani d . 1
C C16 0.29993(15) 0.26598(14) 0.01237(12) 0.0240(3) Uani d . 1
H H16A 0.2346 0.3237 0.0052 0.029 Uiso calc R 1
H H16B 0.2308 0.1758 0.0283 0.029 Uiso calc R 1
C C17 0.38565(16) 0.26196(14) -0.10241(12) 0.0245(3) Uani d . 1
H H17A 0.3135 0.2476 -0.1744 0.029 Uiso calc R 1
H H17B 0.4721 0.3467 -0.1084 0.029 Uiso calc R 1
C C18 0.55038(15) 0.14620(14) -0.18151(12) 0.0219(3) Uani d . 1
C C19 0.59973(17) 0.02693(14) -0.17365(13) 0.0275(3) Uani d . 1
H H19A 0.5400 -0.0424 -0.2348 0.041 Uiso calc R 1
H H19B 0.5798 -0.0059 -0.0922 0.041 Uiso calc R 1
H H19C 0.7118 0.0506 -0.1888 0.041 Uiso calc R 1
C C20 0.35394(16) 0.19163(14) 0.47971(13) 0.0280(3) Uani d . 1
H H20A 0.2678 0.2275 0.4904 0.042 Uiso calc R 1
H H20B 0.3855 0.1690 0.5588 0.042 Uiso calc R 1
H H20C 0.3193 0.1119 0.4238 0.042 Uiso calc R 1
H H1 0.6038(18) 0.3192(16) 0.5852(15) 0.036(5) Uiso d . 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C5 N1 C1 123.66(11) y
C5 N1 H1 116.7(10) ?
C1 N1 H1 119.0(10) ?
O7 N2 O8 123.09(12) ?
O7 N2 C11 118.64(11) ?
O8 N2 C11 118.24(11) ?
C7 O2 C8 115.37(10) ?
C15 O4 C16 116.18(10) ?
C18 O5 C17 116.26(10) ?
C2 C1 N1 118.69(12) y
C2 C1 C6 128.32(11) ?
N1 C1 C6 112.98(10) ?
C1 C2 C7 125.33(12) ?
C1 C2 C3 121.19(11) ?
C7 C2 C3 113.45(10) ?
C4 C3 C2 110.44(10) y
C4 C3 C9 111.72(10) ?
C2 C3 C9 111.78(10) ?
C4 C3 H3 107.6 ?
C2 C3 H3 107.6 ?
C9 C3 H3 107.6 ?
C5 C4 C15 120.69(11) ?
C5 C4 C3 121.04(11) ?
C15 C4 C3 118.15(11) ?
C4 C5 N1 119.15(11) y
C4 C5 C20 127.42(12) ?
N1 C5 C20 113.43(11) ?
C1 C6 H6A 109.5 ?
C1 C6 H6B 109.5 ?
H6A C6 H6B 109.5 ?
C1 C6 H6C 109.5 ?
H6A C6 H6C 109.5 ?
H6B C6 H6C 109.5 ?
O1 C7 O2 122.20(11) ?
O1 C7 C2 122.93(11) ?
O2 C7 C2 114.86(10) ?
O2 C8 H8A 109.5 ?
O2 C8 H8B 109.5 ?
H8A C8 H8B 109.5 ?
O2 C8 H8C 109.5 ?
H8A C8 H8C 109.5 ?
H8B C8 H8C 109.5 ?
C10 C9 C14 118.41(12) ?
C10 C9 C3 120.63(11) ?
C14 C9 C3 120.95(12) ?
C11 C10 C9 119.09(11) ?
C11 C10 H10 120.5 ?
C9 C10 H10 120.5 ?
C12 C11 C10 122.76(12) ?
C12 C11 N2 118.70(11) ?
C10 C11 N2 118.50(11) ?
C11 C12 C13 118.09(12) ?
C11 C12 H12 121.0 ?
C13 C12 H12 121.0 ?
C12 C13 C14 119.96(12) ?
C12 C13 H13 120.0 ?
C14 C13 H13 120.0 ?
C13 C14 C9 121.66(13) ?
C13 C14 H14 119.2 ?
C9 C14 H14 119.2 ?
O3 C15 O4 122.03(12) ?
O3 C15 C4 127.32(12) ?
O4 C15 C4 110.65(10) ?
O4 C16 C17 107.20(10) ?
O4 C16 H16A 110.3 ?
C17 C16 H16A 110.3 ?
O4 C16 H16B 110.3 ?
C17 C16 H16B 110.3 ?
H16A C16 H16B 108.5 ?
O5 C17 C16 107.03(10) ?
O5 C17 H17A 110.3 ?
C16 C17 H17A 110.3 ?
O5 C17 H17B 110.3 ?
C16 C17 H17B 110.3 ?
H17A C17 H17B 108.6 ?
O6 C18 O5 122.29(13) ?
O6 C18 C19 125.35(12) ?
O5 C18 C19 112.35(11) ?
C18 C19 H19A 109.5 ?
C18 C19 H19B 109.5 ?
H19A C19 H19B 109.5 ?
C18 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_distance
_geom_bond_publ_flag
N1 C5 1.3837(17) y
N1 C1 1.3881(16) y
N1 H1 0.893(16) ?
N2 O7 1.2299(14) ?
N2 O8 1.2337(14) ?
N2 C11 1.4719(17) ?
O1 C7 1.2181(14) ?
O2 C7 1.3466(15) ?
O2 C8 1.4541(15) ?
O3 C15 1.2135(15) ?
O4 C15 1.3568(15) ?
O4 C16 1.4495(15) ?
O5 C18 1.3381(15) ?
O5 C17 1.4546(16) ?
O6 C18 1.2146(16) ?
C1 C2 1.3563(17) ?
C1 C6 1.5030(18) ?
C2 C7 1.4716(17) ?
C2 C3 1.5288(17) ?
C3 C4 1.5248(16) ?
C3 C9 1.5327(17) ?
C3 H3 1.0000 ?
C4 C5 1.3530(18) ?
C4 C15 1.4731(18) ?
C5 C20 1.5038(17) ?
C6 H6A 0.9800 ?
C6 H6B 0.9800 ?
C6 H6C 0.9800 ?
C8 H8A 0.9800 ?
C8 H8B 0.9800 ?
C8 H8C 0.9800 ?
C9 C10 1.3925(18) ?
C9 C14 1.3938(17) ?
C10 C11 1.3915(17) ?
C10 H10 0.9500 ?
C11 C12 1.3809(17) ?
C12 C13 1.3867(19) ?
C12 H12 0.9500 ?
C13 C14 1.3921(18) ?
C13 H13 0.9500 ?
C14 H14 0.9500 ?
C16 C17 1.4977(18) ?
C16 H16A 0.9900 ?
C16 H16B 0.9900 ?
C17 H17A 0.9900 ?
C17 H17B 0.9900 ?
C18 C19 1.4902(19) ?
C19 H19A 0.9800 ?
C19 H19B 0.9800 ?
C19 H19C 0.9800 ?
C20 H20A 0.9800 ?
C20 H20B 0.9800 ?
C20 H20C 0.9800 ?
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
N1 H1 O6 1_556 0.893(16) 2.038(17) 2.9241(15) 171.7(15)
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
C5 N1 C1 C2 -13.35(18)
C5 N1 C1 C6 165.67(11)
N1 C1 C2 C7 175.50(11)
C6 C1 C2 C7 -3.3(2)
N1 C1 C2 C3 -6.45(18)
C6 C1 C2 C3 174.70(11)
C1 C2 C3 C4 23.13(16)
C7 C2 C3 C4 -158.61(10)
C1 C2 C3 C9 -101.91(13)
C7 C2 C3 C9 76.35(13)
C2 C3 C4 C5 -23.59(16)
C9 C3 C4 C5 101.48(14)
C2 C3 C4 C15 160.36(10)
C9 C3 C4 C15 -74.57(14)
C15 C4 C5 N1 -176.67(11)
C3 C4 C5 N1 7.38(19)
C15 C4 C5 C20 3.8(2)
C3 C4 C5 C20 -172.12(12)
C1 N1 C5 C4 12.91(19)
C1 N1 C5 C20 -167.52(11)
C8 O2 C7 O1 1.40(17)
C8 O2 C7 C2 -177.80(11)
C1 C2 C7 O1 175.61(12)
C3 C2 C7 O1 -2.57(17)
C1 C2 C7 O2 -5.19(18)
C3 C2 C7 O2 176.63(10)
C4 C3 C9 C10 -52.52(15)
C2 C3 C9 C10 71.80(14)
C4 C3 C9 C14 126.31(12)
C2 C3 C9 C14 -109.37(13)
C14 C9 C10 C11 -1.26(17)
C3 C9 C10 C11 177.60(11)
C9 C10 C11 C12 0.60(18)
C9 C10 C11 N2 -177.15(11)
O7 N2 C11 C12 -174.04(12)
O8 N2 C11 C12 3.92(17)
O7 N2 C11 C10 3.81(17)
O8 N2 C11 C10 -178.23(11)
C10 C11 C12 C13 0.80(19)
N2 C11 C12 C13 178.55(11)
C11 C12 C13 C14 -1.51(19)
C12 C13 C14 C9 0.9(2)
C10 C9 C14 C13 0.55(19)
C3 C9 C14 C13 -178.30(11)
C16 O4 C15 O3 -3.74(18)
C16 O4 C15 C4 176.30(10)
C5 C4 C15 O3 8.4(2)
C3 C4 C15 O3 -175.58(13)
C5 C4 C15 O4 -171.69(11)
C3 C4 C15 O4 4.37(16)
C15 O4 C16 C17 -153.22(11)
C18 O5 C17 C16 -169.05(10)
O4 C16 C17 O5 73.40(13)
C17 O5 C18 O6 2.35(18)
C17 O5 C18 C19 -176.54(11)
