#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/72/2207215.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_2207215
loop_
_publ_author_name
'Vrábel, Viktor'
'Fronc, Marek'
'Svoboda, Ingrid'
'Marchalín, Štefan'
'Baumlová, Barbora'
_publ_section_title
;Diethyl
 2,6-dimethyl-4-[5-(4-nitrophenyl)-2-furyl]-1,4-dihydropyridine-3,5-dicarboxylate
;
_journal_coeditor_code           ER6024
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3592
_journal_page_last               o3594
_journal_paper_doi               10.1107/S1600536805031430
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C23 H24 N2 O7'
_chemical_formula_moiety         'C23 H24 N2 O7'
_chemical_formula_sum            'C23 H24 N2 O7'
_chemical_formula_weight         440.44
_chemical_name_systematic
;
Diethyl
2,6-dimethyl-4-[5-(4-nitrophenyl)-2-furyl]-1,4-dihydropyridine-3,5-
dicarboxylate
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.940(2)
_cell_length_b                   8.1430(10)
_cell_length_c                   20.114(2)
_cell_measurement_reflns_used    2029
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      19.10
_cell_measurement_theta_min      4.50
_cell_volume                     2119.4(5)
_computing_cell_refinement
;
CrysAlis CCD
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2002)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2002)
;
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur CCD'
_diffrn_measurement_method       'area detector ω and φ'
_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  0.0589
_diffrn_reflns_av_sigmaI/netI    0.0372
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13748
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         4.15
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.504
_refine_ls_abs_structure_details rm
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         2222
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0636
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.1339P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1697
_refine_ls_wR_factor_ref         0.1862
_reflns_number_gt                1615
_reflns_number_total             2222
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            er6024.cif
_cod_data_source_block           I
_cod_database_code               2207215
_cod_database_fobs_code          2207215
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, 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
C2 -0.0022(4) 0.9705(6) 0.8295(3) 0.0487(11) Uani d . 1 C
C3 0.0861(4) 1.0382(6) 0.8495(2) 0.0446(10) Uani d . 1 C
C4 0.1394(4) 0.9737(6) 0.9109(2) 0.0454(10) Uani d . 1 C
H4 0.1744 1.0667 0.9321 0.054 Uiso calc R 1 H
C5 0.0627(4) 0.9075(7) 0.9598(3) 0.0540(12) Uani d . 1 C
C6 -0.0281(4) 0.8476(6) 0.9365(3) 0.0517(12) Uani d . 1 C
C7 0.2205(3) 0.8546(6) 0.8907(2) 0.0446(10) Uani d . 1 C
C8 0.2294(4) 0.7571(7) 0.8377(3) 0.0626(14) Uani d . 1 C
H8 0.1840 0.7489 0.8020 0.075 Uiso calc R 1 H
C9 0.3215(4) 0.6698(7) 0.8473(3) 0.0586(13) Uani d . 1 C
H9 0.3495 0.5927 0.8183 0.070 Uiso calc R 1 H
C10 0.3623(3) 0.7172(6) 0.9059(3) 0.0468(10) Uani d . 1 C
C12 0.4504(4) 0.6726(5) 0.9462(3) 0.0472(11) Uani d . 1 C
C13 0.5256(4) 0.5706(6) 0.9217(3) 0.0569(13) Uani d . 1 C
H13 0.5221 0.5353 0.8778 0.068 Uiso calc R 1 H
C14 0.6050(4) 0.5206(7) 0.9605(3) 0.0639(15) Uani d . 1 C
H14 0.6555 0.4509 0.9435 0.077 Uiso calc R 1 H
C15 0.6103(4) 0.5737(6) 1.0253(3) 0.0576(14) Uani d . 1 C
C16 0.5376(4) 0.6788(7) 1.0503(3) 0.0641(15) Uani d . 1 C
H16 0.5417 0.7162 1.0939 0.077 Uiso calc R 1 H
C17 0.4591(4) 0.7274(6) 1.0097(3) 0.0567(13) Uani d . 1 C
H17 0.4100 0.8004 1.0260 0.068 Uiso calc R 1 H
C21 -0.0569(4) 0.9941(8) 0.7637(3) 0.0635(14) Uani d . 1 C
H21A -0.0738 1.1080 0.7580 0.076 Uiso calc R 1 H
H21B -0.1191 0.9299 0.7631 0.076 Uiso calc R 1 H
H21C -0.0124 0.9593 0.7282 0.076 Uiso calc R 1 H
C31 0.1426(4) 1.1659(6) 0.8159(3) 0.0511(12) Uani d . 1 C
C32 0.1400(5) 1.3689(9) 0.7359(4) 0.088(2) Uani d D 1 C
H32A 0.1931 1.3223 0.7075 0.105 Uiso calc R 1 H
H32B 0.1724 1.4440 0.7669 0.105 Uiso calc R 1 H
C33 0.0616(7) 1.4560(12) 0.6953(5) 0.124(4) Uani d D 1 C
H33A 0.0316 1.3810 0.6639 0.149 Uiso calc R 1 H
H33B 0.0939 1.5450 0.6718 0.149 Uiso calc R 1 H
H33C 0.0085 1.4986 0.7238 0.149 Uiso calc R 1 H
C51 0.0849(5) 0.9072(9) 1.0306(3) 0.0728(18) Uani d . 1 C
C52 0.1900(8) 1.012(2) 1.1124(4) 0.174(7) Uani d D 1 C
H52A 0.1316 0.9719 1.1378 0.209 Uiso calc R 1 H
H52B 0.1925 1.1308 1.1173 0.209 Uiso calc R 1 H
C53 0.2844(4) 0.9411(7) 1.1379(3) 0.197(8) Uani d D 1 C
H53A 0.2901 0.9641 1.1846 0.236 Uiso calc R 1 H
H53B 0.3425 0.9874 1.1149 0.236 Uiso calc R 1 H
H53C 0.2832 0.8244 1.1311 0.236 Uiso calc R 1 H
C61 -0.1069(4) 0.7616(7) 0.9757(3) 0.0709(16) Uani d R 1 C
H61A -0.0772 0.6651 0.9953 0.085 Uiso calc R 1 H
H61B -0.1633 0.7307 0.9474 0.085 Uiso calc R 1 H
H61C -0.1318 0.8329 1.0102 0.085 Uiso calc R 1 H
N1 -0.0497(3) 0.8622(5) 0.8702(2) 0.0544(10) Uani d . 1 N
H1 -0.0961 0.7989 0.8535 0.065 Uiso calc R 1 H
N15 0.6922(4) 0.5165(7) 1.0683(4) 0.0804(17) Uani d . 1 N
O11 0.2994(2) 0.8319(4) 0.93239(17) 0.0457(8) Uani d . 1 O
O15 0.7581(4) 0.4352(7) 1.0465(4) 0.115(2) Uani d . 1 O
O16 0.6860(5) 0.5505(9) 1.1282(4) 0.123(2) Uani d . 1 O
O31 0.0870(3) 1.2428(5) 0.7706(2) 0.0651(10) Uani d . 1 O
O32 0.2294(3) 1.2048(5) 0.8288(2) 0.0672(11) Uani d . 1 O
O51 0.1766(4) 0.9719(7) 1.0446(2) 0.0816(14) Uani d . 1 O
O52 0.0285(5) 0.8658(11) 1.0740(3) 0.129(2) Uani d . 1 O
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C3 C2 N1 118.6(5) y
C3 C2 C21 127.8(5) ?
N1 C2 C21 113.6(4) ?
C2 C3 C31 126.4(4) ?
C2 C3 C4 119.7(4) y
C31 C3 C4 113.8(4) ?
C7 C4 C5 114.4(4) ?
C7 C4 C3 109.1(4) y
C5 C4 C3 111.1(4) ?
C7 C4 H4 107.3 ?
C5 C4 H4 107.3 ?
C3 C4 H4 107.3 ?
C6 C5 C51 120.6(5) ?
C6 C5 C4 118.5(5) ?
C51 C5 C4 120.9(5) ?
C5 C6 N1 118.8(5) ?
C5 C6 C61 126.0(5) ?
N1 C6 C61 115.1(5) ?
C8 C7 O11 110.7(4) ?
C8 C7 C4 131.9(5) ?
O11 C7 C4 117.3(4) ?
C7 C8 C9 105.4(5) ?
C7 C8 H8 127.3 ?
C9 C8 H8 127.3 ?
C10 C9 C8 107.9(5) ?
C10 C9 H9 126.0 ?
C8 C9 H9 126.0 ?
O11 C10 C9 107.9(4) ?
O11 C10 C12 115.4(4) ?
C9 C10 C12 136.7(5) ?
C17 C12 C13 118.5(5) ?
C17 C12 C10 120.7(4) ?
C13 C12 C10 120.7(5) ?
C14 C13 C12 120.9(5) ?
C14 C13 H13 119.5 ?
C12 C13 H13 119.5 ?
C13 C14 C15 119.3(5) ?
C13 C14 H14 120.3 ?
C15 C14 H14 120.3 ?
C16 C15 C14 120.7(5) ?
C16 C15 N15 119.2(6) ?
C14 C15 N15 120.1(5) ?
C17 C16 C15 118.3(6) ?
C17 C16 H16 120.8 ?
C15 C16 H16 120.8 ?
C12 C17 C16 122.1(5) ?
C12 C17 H17 119.0 ?
C16 C17 H17 119.0 ?
C2 C21 H21A 109.5 ?
C2 C21 H21B 109.5 ?
H21A C21 H21B 109.5 ?
C2 C21 H21C 109.5 ?
H21A C21 H21C 109.5 ?
H21B C21 H21C 109.5 ?
O32 C31 O31 122.5(5) y
O32 C31 C3 124.5(5) ?
O31 C31 C3 113.0(4) ?
O31 C32 C33 106.6(5) ?
O31 C32 H32A 110.4 ?
C33 C32 H32A 110.4 ?
O31 C32 H32B 110.4 ?
C33 C32 H32B 110.4 ?
H32A C32 H32B 108.6 ?
C32 C33 H33A 109.5 ?
C32 C33 H33B 109.5 ?
H33A C33 H33B 109.5 ?
C32 C33 H33C 109.5 ?
H33A C33 H33C 109.5 ?
H33B C33 H33C 109.5 ?
O52 C51 O51 120.5(6) y
O52 C51 C5 126.9(7) ?
O51 C51 C5 112.5(5) ?
O51 C52 C53 110.6(7) ?
O51 C52 H52A 109.5 ?
C53 C52 H52A 109.5 ?
O51 C52 H52B 109.5 ?
C53 C52 H52B 109.5 ?
H52A C52 H52B 108.1 ?
C52 C53 H53A 109.5 ?
C52 C53 H53B 109.5 ?
H53A C53 H53B 109.5 ?
C52 C53 H53C 109.5 ?
H53A C53 H53C 109.5 ?
H53B C53 H53C 109.5 ?
C6 C61 H61A 109.5 ?
C6 C61 H61B 109.5 ?
H61A C61 H61B 109.5 ?
C6 C61 H61C 109.5 ?
H61A C61 H61C 109.5 ?
H61B C61 H61C 109.5 ?
C2 N1 C6 123.7(5) y
C2 N1 H1 118.2 ?
C6 N1 H1 118.2 ?
O15 N15 O16 122.6(6) y
O15 N15 C15 119.8(7) ?
O16 N15 C15 117.5(6) ?
C7 O11 C10 108.0(4) y
C31 O31 C32 114.8(4) ?
C51 O51 C52 113.9(7) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C2 C3 1.331(7) y
C2 N1 1.351(7) y
C2 C21 1.513(7) ?
C3 C31 1.440(7) ?
C3 C4 1.509(6) ?
C4 C7 1.486(7) y
C4 C5 1.498(7) ?
C4 H4 0.9800 ?
C5 C6 1.356(7) y
C5 C51 1.453(8) ?
C6 N1 1.368(7) ?
C6 C61 1.467(8) ?
C7 C8 1.333(7) y
C7 O11 1.335(5) ?
C8 C9 1.401(8) y
C8 H8 0.9300 ?
C9 C10 1.349(8) ?
C9 H9 0.9300 ?
C10 O11 1.349(5) ?
C10 C12 1.444(7) y
C12 C17 1.358(7) ?
C12 C13 1.372(7) ?
C13 C14 1.352(8) ?
C13 H13 0.9300 ?
C14 C15 1.377(9) ?
C14 H14 0.9300 ?
C15 C16 1.367(8) ?
C15 N15 1.444(7) y
C16 C17 1.362(8) ?
C16 H16 0.9300 ?
C17 H17 0.9300 ?
C21 H21A 0.9600 ?
C21 H21B 0.9600 ?
C21 H21C 0.9600 ?
C31 O32 1.196(6) ?
C31 O31 1.319(6) ?
C32 O31 1.418(7) ?
C32 C33 1.484(5) y
C32 H32A 0.9700 ?
C32 H32B 0.9700 ?
C33 H33A 0.9600 ?
C33 H33B 0.9600 ?
C33 H33C 0.9600 ?
C51 O52 1.187(8) ?
C51 O51 1.328(8) ?
C52 O51 1.414(9) ?
C52 C53 1.447(5) y
C52 H52A 0.9700 ?
C52 H52B 0.9700 ?
C53 H53A 0.9600 ?
C53 H53B 0.9600 ?
C53 H53C 0.9600 ?
C61 H61A 0.9600 ?
C61 H61B 0.9600 ?
C61 H61C 0.9600 ?
N1 H1 0.8600 ?
N15 O15 1.165(8) ?
N15 O16 1.239(10) ?
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 O32 4_475 0.86 2.31 3.027(6) 141
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
_geom_torsion_publ_flag
N1 C2 C3 C31 -174.1(5) ?
C21 C2 C3 C31 8.6(8) ?
N1 C2 C3 C4 9.8(7) ?
C21 C2 C3 C4 -167.5(5) ?
C2 C3 C4 C7 96.4(5) y
C31 C3 C4 C7 -80.2(5) ?
C2 C3 C4 C5 -30.6(6) ?
C31 C3 C4 C5 152.8(4) ?
C7 C4 C5 C6 -96.2(5) y
C3 C4 C5 C6 27.8(6) ?
C7 C4 C5 C51 83.8(6) ?
C3 C4 C5 C51 -152.2(5) ?
C51 C5 C6 N1 174.8(5) ?
C4 C5 C6 N1 -5.3(7) ?
C51 C5 C6 C61 -7.3(9) ?
C4 C5 C6 C61 172.6(5) ?
C5 C4 C7 C8 97.8(7) ?
C3 C4 C7 C8 -27.3(8) ?
C5 C4 C7 O11 -79.7(5) ?
C3 C4 C7 O11 155.2(4) ?
O11 C7 C8 C9 -0.9(6) ?
C4 C7 C8 C9 -178.5(5) ?
C7 C8 C9 C10 1.0(6) ?
C8 C9 C10 O11 -0.8(6) ?
C8 C9 C10 C12 176.4(5) ?
O11 C10 C12 C17 8.7(7) ?
C9 C10 C12 C17 -168.4(6) ?
O11 C10 C12 C13 -173.0(4) ?
C9 C10 C12 C13 10.0(9) y
C17 C12 C13 C14 2.4(8) ?
C10 C12 C13 C14 -176.0(5) ?
C12 C13 C14 C15 -0.4(8) ?
C13 C14 C15 C16 -1.4(8) ?
C13 C14 C15 N15 177.6(5) ?
C14 C15 C16 C17 1.0(8) ?
N15 C15 C16 C17 -178.0(5) ?
C13 C12 C17 C16 -2.8(8) ?
C10 C12 C17 C16 175.6(5) ?
C15 C16 C17 C12 1.1(8) ?
C2 C3 C31 O32 -166.8(5) y
C4 C3 C31 O32 9.5(7) y
C2 C3 C31 O31 16.1(7) y
C4 C3 C31 O31 -167.6(4) y
C6 C5 C51 O52 -4.1(12) y
C4 C5 C51 O52 176.0(8) y
C6 C5 C51 O51 -179.3(5) y
C4 C5 C51 O51 0.8(8) ?
C3 C2 N1 C6 17.0(7) ?
C21 C2 N1 C6 -165.3(5) ?
C5 C6 N1 C2 -19.4(8) ?
C61 C6 N1 C2 162.4(5) ?
C16 C15 N15 O15 -175.3(6) y
C14 C15 N15 O15 5.8(9) ?
C16 C15 N15 O16 8.2(9) y
C14 C15 N15 O16 -170.7(7) ?
C8 C7 O11 C10 0.4(5) ?
C4 C7 O11 C10 178.4(4) ?
C9 C10 O11 C7 0.2(5) ?
C12 C10 O11 C7 -177.6(4) ?
O32 C31 O31 C32 3.3(8) ?
C3 C31 O31 C32 -179.5(5) ?
C33 C32 O31 C31 -171.6(6) ?
O52 C51 O51 C52 -10.9(12) ?
C5 C51 O51 C52 164.6(7) ?
C53 C52 O51 C51 128.0(10) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 1030155
