#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/27/2222777.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_2222777
loop_
_publ_author_name
'Wu, De-Hong'
'Hu, Ling'
_publ_section_title
;
 3,5-Bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine-4-carboxylic
 acid
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1748
_journal_paper_doi               10.1107/S1600536809024945
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H19 N O6'
_chemical_formula_moiety         'C14 H19 N O6'
_chemical_formula_sum            'C14 H19 N O6'
_chemical_formula_weight         297.30
_chemical_name_systematic
;
3,5-Bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine-4-carboxylic acid
;
_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                104.10(3)
_cell_angle_beta                 97.808(9)
_cell_angle_gamma                111.658(10)
_cell_formula_units_Z            2
_cell_length_a                   7.445(4)
_cell_length_b                   9.864(5)
_cell_length_c                   11.908(2)
_cell_measurement_reflns_used    2034
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.34
_cell_volume                     763.1(6)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      291(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Rigaku SCXmini'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0312
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6950
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.04
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.237
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2969
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0627
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.115P)²+0.1066P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1802
_refine_ls_wR_factor_ref         0.1969
_reflns_number_gt                2241
_reflns_number_total             2969
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            kj2129.cif
_cod_data_source_block           I
_cod_original_cell_volume        763.2(6)
_cod_database_code               2222777
_cod_database_fobs_code          2222777
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.5752(3) 0.3833(2) 0.24556(18) 0.0403(5) Uani d . 1 . .
H H1A 0.4891 0.4029 0.2968 0.048 Uiso calc R 1 . .
C C2 0.5338(3) 0.4308(2) 0.13568(18) 0.0418(5) Uani d . 1 . .
C C3 0.7927(3) 0.4825(2) 0.31506(19) 0.0471(5) Uani d . 1 . .
C C4 0.9329(3) 0.4276(3) 0.29898(19) 0.0482(5) Uani d . 1 . .
C C5 0.6783(3) 0.1670(2) 0.19748(19) 0.0447(5) Uani d . 1 . .
C C6 0.5295(3) 0.2141(2) 0.21075(17) 0.0403(5) Uani d . 1 . .
C C7 1.1547(3) 0.5129(3) 0.3518(3) 0.0700(7) Uani d . 1 . .
H H7A 1.1858 0.6168 0.3980 0.105 Uiso calc R 1 . .
H H7B 1.2223 0.5136 0.2887 0.105 Uiso calc R 1 . .
H H7C 1.1974 0.4627 0.4026 0.105 Uiso calc R 1 . .
C C8 0.8460(4) 0.6388(3) 0.3946(2) 0.0691(7) Uani d . 1 A .
C C9 0.7022(9) 0.7955(6) 0.5064(4) 0.0796(16) Uani d PD 0.742(10) A 2
H H9A 0.8340 0.8514 0.5609 0.096 Uiso calc PR 0.742(10) A 2
H H9B 0.6041 0.7752 0.5532 0.096 Uiso calc PR 0.742(10) A 2
C C10 0.6670(9) 0.8858(5) 0.4323(6) 0.109(2) Uani d PD 0.742(10) A 2
H H10D 0.6721 0.9802 0.4824 0.164 Uiso calc PR 0.742(10) A 2
H H10E 0.5379 0.8281 0.3771 0.164 Uiso calc PR 0.742(10) A 2
H H10F 0.7678 0.9085 0.3887 0.164 Uiso calc PR 0.742(10) A 2
C C11 0.6588(4) 0.0046(3) 0.1497(3) 0.0639(7) Uani d . 1 . .
H H11A 0.5206 -0.0659 0.1283 0.096 Uiso calc R 1 . .
H H11B 0.7320 -0.0178 0.2100 0.096 Uiso calc R 1 . .
H H11C 0.7114 -0.0059 0.0804 0.096 Uiso calc R 1 . .
C C12 0.3169(3) 0.1123(2) 0.18269(19) 0.0439(5) Uani d . 1 . .
C C13 0.0631(4) -0.1451(3) 0.1230(3) 0.0734(8) Uani d . 1 . .
H H13A -0.0118 -0.1280 0.0588 0.088 Uiso calc R 1 . .
H H13B 0.0062 -0.1315 0.1913 0.088 Uiso calc R 1 . .
C C14 0.0555(5) -0.3023(3) 0.0839(4) 0.0916(11) Uani d . 1 . .
H H14A -0.0808 -0.3768 0.0618 0.137 Uiso calc R 1 . .
H H14B 0.1301 -0.3177 0.1482 0.137 Uiso calc R 1 . .
H H14C 0.1121 -0.3142 0.0164 0.137 Uiso calc R 1 . .
C C9' 0.7854(18) 0.8432(14) 0.4818(12) 0.065(4) Uiso d PD 0.258(10) A 1
H H9'A 0.8895 0.8831 0.5551 0.078 Uiso calc PR 0.258(10) A 1
H H9'B 0.8364 0.8910 0.4238 0.078 Uiso calc PR 0.258(10) A 1
C C10' 0.5997(16) 0.8597(14) 0.5033(11) 0.070(4) Uiso d PD 0.258(10) A 1
H H10A 0.6312 0.9662 0.5417 0.105 Uiso calc PR 0.258(10) A 1
H H10B 0.5459 0.8009 0.5538 0.105 Uiso calc PR 0.258(10) A 1
H H10C 0.5030 0.8227 0.4283 0.105 Uiso calc PR 0.258(10) A 1
N N1 0.8729(2) 0.2761(2) 0.23053(18) 0.0502(5) Uani d . 1 . .
H H1D 0.9620 0.2484 0.2073 0.060 Uiso calc R 1 . .
O O1 0.5162(3) 0.35326(19) 0.03480(14) 0.0690(5) Uani d . 1 . .
O O2 0.5283(3) 0.56518(19) 0.15897(15) 0.0760(6) Uani d . 1 . .
H H2A 0.5144 0.5865 0.0969 0.114 Uiso calc R 1 . .
O O3 1.0104(4) 0.7427(3) 0.4291(3) 0.1314(12) Uani d . 1 . .
O O4 0.6867(3) 0.6538(2) 0.42828(16) 0.0787(6) Uani d . 1 . .
O O5 0.1878(2) 0.16074(18) 0.18443(16) 0.0603(5) Uani d . 1 . .
O O6 0.2733(2) -0.03741(17) 0.15535(18) 0.0639(5) Uani 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 C1 C2 . . 111.10(16) ?
C6 C1 C3 . . 111.42(16) ?
C2 C1 C3 . . 108.83(16) ?
C6 C1 H1A . . 108.5 ?
C2 C1 H1A . . 108.5 ?
C3 C1 H1A . . 108.5 ?
O1 C2 O2 . . 122.4(2) ?
O1 C2 C1 . . 122.99(17) ?
O2 C2 C1 . . 114.51(17) ?
C4 C3 C8 . . 121.5(2) ?
C4 C3 C1 . . 119.72(19) ?
C8 C3 C1 . . 118.72(19) ?
C3 C4 N1 . . 119.07(18) ?
C3 C4 C7 . . 127.0(2) ?
N1 C4 C7 . . 113.86(19) ?
C6 C5 N1 . . 118.93(18) ?
C6 C5 C11 . . 127.8(2) ?
N1 C5 C11 . . 113.28(17) ?
C5 C6 C12 . . 125.35(19) ?
C5 C6 C1 . . 120.07(18) ?
C12 C6 C1 . . 114.31(16) ?
C4 C7 H7A . . 109.5 ?
C4 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C4 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
O3 C8 O4 . . 122.4(3) ?
O3 C8 C3 . . 125.8(3) ?
O4 C8 C3 . . 111.8(2) ?
O4 C9 C10 . . 107.7(4) ?
O4 C9 H9A . . 110.2 ?
C10 C9 H9A . . 110.2 ?
O4 C9 H9B . . 110.2 ?
C10 C9 H9B . . 110.2 ?
H9A C9 H9B . . 108.5 ?
C9 C10 H10D . . 109.5 ?
C9 C10 H10E . . 109.5 ?
H10D C10 H10E . . 109.5 ?
C9 C10 H10F . . 109.5 ?
H10D C10 H10F . . 109.5 ?
H10E C10 H10F . . 109.5 ?
C5 C11 H11A . . 109.5 ?
C5 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C5 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
O5 C12 O6 . . 122.05(19) ?
O5 C12 C6 . . 122.53(19) ?
O6 C12 C6 . . 115.42(17) ?
O6 C13 C14 . . 106.9(2) ?
O6 C13 H13A . . 110.3 ?
C14 C13 H13A . . 110.3 ?
O6 C13 H13B . . 110.3 ?
C14 C13 H13B . . 110.3 ?
H13A C13 H13B . . 108.6 ?
C13 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C13 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C10' C9' O4 . . 97.3(9) ?
C10' C9' H9'A . . 112.3 ?
O4 C9' H9'A . . 112.3 ?
C10' C9' H9'B . . 112.3 ?
O4 C9' H9'B . . 112.3 ?
H9'A C9' H9'B . . 109.9 ?
C9' C10' H10A . . 109.5 ?
C9' C10' H10B . . 109.5 ?
H10A C10' H10B . . 109.5 ?
C9' C10' H10C . . 109.5 ?
H10A C10' H10C . . 109.5 ?
H10B C10' H10C . . 109.5 ?
C5 N1 C4 . . 123.75(16) ?
C5 N1 H1D . . 118.1 ?
C4 N1 H1D . . 118.1 ?
C2 O2 H2A . . 109.5 ?
C8 O4 C9 . . 121.9(3) ?
C8 O4 C9' . . 97.6(5) ?
C12 O6 C13 . . 117.96(17) ?
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
C1 C6 . 1.510(3) ?
C1 C2 . 1.524(3) ?
C1 C3 . 1.528(3) ?
C1 H1A . 0.9800 ?
C2 O1 . 1.217(3) ?
C2 O2 . 1.304(2) ?
C3 C4 . 1.357(3) ?
C3 C8 . 1.472(3) ?
C4 N1 . 1.383(3) ?
C4 C7 . 1.505(3) ?
C5 C6 . 1.363(3) ?
C5 N1 . 1.378(3) ?
C5 C11 . 1.508(3) ?
C6 C12 . 1.465(3) ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C8 O3 . 1.204(3) ?
C8 O4 . 1.348(3) ?
C9 O4 . 1.432(4) ?
C9 C10 . 1.461(8) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 H10D . 0.9600 ?
C10 H10E . 0.9600 ?
C10 H10F . 0.9600 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 O5 . 1.222(2) ?
C12 O6 . 1.332(2) ?
C13 O6 . 1.462(3) ?
C13 C14 . 1.483(4) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C9' C10' . 1.499(15) ?
C9' O4 . 1.649(12) ?
C9' H9'A . 0.9700 ?
C9' H9'B . 0.9700 ?
C10' H10A . 0.9600 ?
C10' H10B . 0.9600 ?
C10' H10C . 0.9600 ?
N1 H1D . 0.8600 ?
O2 H2A . 0.8200 ?
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 H1D O5 1_655 0.86 2.17 3.018(2) 166.8
O2 H2A O1 2_665 0.82 1.82 2.641(2) 175.9
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 O1 . . . . -17.2(3) ?
C3 C1 C2 O1 . . . . 105.9(2) ?
C6 C1 C2 O2 . . . . 166.01(18) ?
C3 C1 C2 O2 . . . . -70.9(2) ?
C6 C1 C3 C4 . . . . 25.8(3) ?
C2 C1 C3 C4 . . . . -97.1(2) ?
C6 C1 C3 C8 . . . . -156.7(2) ?
C2 C1 C3 C8 . . . . 80.4(2) ?
C8 C3 C4 N1 . . . . 175.1(2) ?
C1 C3 C4 N1 . . . . -7.5(3) ?
C8 C3 C4 C7 . . . . -2.6(4) ?
C1 C3 C4 C7 . . . . 174.8(2) ?
N1 C5 C6 C12 . . . . -178.35(18) ?
C11 C5 C6 C12 . . . . 1.5(4) ?
N1 C5 C6 C1 . . . . 8.0(3) ?
C11 C5 C6 C1 . . . . -172.2(2) ?
C2 C1 C6 C5 . . . . 95.5(2) ?
C3 C1 C6 C5 . . . . -26.0(3) ?
C2 C1 C6 C12 . . . . -78.8(2) ?
C3 C1 C6 C12 . . . . 159.62(17) ?
C4 C3 C8 O3 . . . . 18.6(5) ?
C1 C3 C8 O3 . . . . -158.8(3) ?
C4 C3 C8 O4 . . . . -160.1(2) ?
C1 C3 C8 O4 . . . . 22.5(3) ?
C5 C6 C12 O5 . . . . -172.2(2) ?
C1 C6 C12 O5 . . . . 1.8(3) ?
C5 C6 C12 O6 . . . . 8.0(3) ?
C1 C6 C12 O6 . . . . -177.98(17) ?
C6 C5 N1 C4 . . . . 13.9(3) ?
C11 C5 N1 C4 . . . . -166.0(2) ?
C3 C4 N1 C5 . . . . -14.1(3) ?
C7 C4 N1 C5 . . . . 163.9(2) ?
O3 C8 O4 C9 . . . . 0.8(5) ?
C3 C8 O4 C9 . . . . 179.6(3) ?
O3 C8 O4 C9' . . . . 15.3(6) ?
C3 C8 O4 C9' . . . . -165.9(5) ?
C10 C9 O4 C8 . . . . 89.7(5) ?
C10' C9' O4 C8 . . . . 172.6(8) ?
O5 C12 O6 C13 . . . . 2.0(3) ?
C6 C12 O6 C13 . . . . -178.2(2) ?
C14 C13 O6 C12 . . . . 173.7(2) ?
