#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:58:33 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202018 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/18/8101885.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8101885
loop_
_publ_author_name
'da Silva, A. F.'
'de Simone, C. A.'
'Sant'Ana, A. E. G.'
'Pereira, M. A.'
'Malta, V. R. S.'
_publ_section_title
;
Crystal structure of diethyl 4-phenyl-2,6-dimethyl-3,5-pyridinedicarboxylate, 
C₁₉H₂₁NO₄, an multidrug resistance reversal agent from Jatropha 
elliptica
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              611
_journal_page_last               612
_journal_volume                  220
_journal_year                    2005
_chemical_formula_moiety         'C19 H21 N O4'
_chemical_formula_sum            'C19 H21 N O4'
_chemical_formula_weight         327.37
_chemical_name_systematic
;
 diethyl 4-phenyl-2,6-dimethyl-3,5-pyridinedicarboxylate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 99.366(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   11.204(5)
_cell_length_b                   8.368(5)
_cell_length_c                   18.817(5)
_cell_measurement_reflns_used    3765
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     1740.7(14)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'HKL Denzo and Scalepack (Otw. & Minor 1997)'
_computing_molecular_graphics    'Ortep3 (Farrugia,1997)'
_computing_publication_material  'WinGX-Routine (Farrugia,1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick,1997)'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'Nonius 95mm KappaCCD'
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0425
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            7043
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.67
_diffrn_source                   'Enraf-Nonius FR590 CCD'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.020(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3940
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0544
_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)+(0.0644P)²+0.4551P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1364
_refine_ls_wR_factor_ref         0.1536
_reflns_number_gt                2815
_reflns_number_total             3940
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-1673.cff
_cod_data_source_block           aldenir2
_cod_depositor_comments
;
The following automatic conversions were performed:
'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      P12(1)/n1
_cod_database_code               8101885
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.74779(10) 0.39408(14) 0.96434(7) 0.0552(3) Uani 1 4 e d . . .
O4 O 0.48900(11) -0.06963(17) 0.75790(7) 0.0642(4) Uani 1 4 e d . . .
C3 C 0.71883(14) 0.1213(2) 0.94054(9) 0.0486(4) Uani 1 4 e d . . .
C20 C 0.83976(17) 0.0045(3) 1.05494(11) 0.0680(5) Uani 1 4 e d . . .
H20A H 0.8358 -0.0882 1.0845 0.102 Uiso 1 4 e calc R . .
H20B H 0.8343 0.0991 1.0831 0.102 Uiso 1 4 e calc R . .
H20C H 0.9151 0.0047 1.0368 0.102 Uiso 1 4 e calc R . .
N1 N 0.66144(14) -0.12327(18) 0.99116(8) 0.0580(4) Uani 1 4 e d . . .
C9 C 0.8269(2) 0.6162(3) 0.90200(14) 0.0831(7) Uani 1 4 e d . . .
H9A H 0.8743 0.7120 0.9096 0.125 Uiso 1 4 e calc R . .
H9B H 0.7470 0.6421 0.8779 0.125 Uiso 1 4 e calc R . .
H9C H 0.8643 0.5433 0.8729 0.125 Uiso 1 4 e calc R . .
O2 O 0.90728(11) 0.25514(18) 0.94041(10) 0.0769(5) Uani 1 4 e d . . .
C5 C 0.54689(15) -0.0241(2) 0.88145(10) 0.0533(4) Uani 1 4 e d . . .
C4 C 0.62139(14) 0.1110(2) 0.88377(9) 0.0490(4) Uani 1 4 e d . . .
C10 C 0.59785(14) 0.2389(2) 0.82837(10) 0.0513(4) Uani 1 4 e d . . .
C7 C 0.80279(14) 0.2618(2) 0.94745(10) 0.0526(4) Uani 1 4 e d . . .
C2 C 0.73627(15) 0.0012(2) 0.99266(10) 0.0526(4) Uani 1 4 e d . . .
C17 C 0.3991(2) -0.0925(3) 0.69325(12) 0.0768(6) Uani 1 4 e d . . .
H17A H 0.3350 -0.1613 0.7044 0.092 Uiso 1 4 e calc R . .
H17B H 0.4366 -0.1447 0.6565 0.092 Uiso 1 4 e calc R . .
O1 O 0.34197(13) -0.0601(3) 0.82460(9) 0.0998(7) Uani 1 4 e d . . .
C16 C 0.44668(16) -0.0518(2) 0.81967(11) 0.0606(5) Uani 1 4 e d . . .
C6 C 0.56829(16) -0.1373(2) 0.93654(10) 0.0568(5) Uani 1 4 e d . . .
C8 C 0.81909(18) 0.5404(2) 0.97285(12) 0.0645(5) Uani 1 4 e d . . .
H8A H 0.9000 0.5162 0.9975 0.077 Uiso 1 4 e calc R . .
H8B H 0.7826 0.6151 1.0024 0.077 Uiso 1 4 e calc R . .
C15 C 0.48686(16) 0.3183(3) 0.81703(12) 0.0657(5) Uani 1 4 e d . . .
H15 H 0.4276 0.2924 0.8444 0.079 Uiso 1 4 e calc R . .
C11 C 0.68470(16) 0.2820(2) 0.78738(10) 0.0579(5) Uani 1 4 e d . . .
H11 H 0.7596 0.2313 0.7950 0.069 Uiso 1 4 e calc R . .
C12 C 0.6615(2) 0.3992(2) 0.73539(11) 0.0684(5) Uani 1 4 e d . . .
H12 H 0.7204 0.4259 0.7078 0.082 Uiso 1 4 e calc R . .
C14 C 0.4654(2) 0.4365(3) 0.76447(14) 0.0792(7) Uani 1 4 e d . . .
H14 H 0.3913 0.4890 0.7567 0.095 Uiso 1 4 e calc R . .
C13 C 0.5522(2) 0.4766(3) 0.72410(13) 0.0758(6) Uani 1 4 e d . . .
H13 H 0.5371 0.5559 0.6892 0.091 Uiso 1 4 e calc R . .
C19 C 0.4928(2) -0.2857(3) 0.93826(13) 0.0773(6) Uani 1 4 e d . . .
H19A H 0.5230 -0.3467 0.9806 0.116 Uiso 1 4 e calc R . .
H19B H 0.4971 -0.3490 0.8962 0.116 Uiso 1 4 e calc R . .
H19C H 0.4103 -0.2561 0.9391 0.116 Uiso 1 4 e calc R . .
C18 C 0.3467(2) 0.0629(3) 0.66519(14) 0.0911(8) Uani 1 4 e d . . .
H18A H 0.2880 0.0447 0.6228 0.137 Uiso 1 4 e calc R . .
H18B H 0.4100 0.1304 0.6534 0.137 Uiso 1 4 e calc R . .
H18C H 0.3084 0.1139 0.7012 0.137 Uiso 1 4 e calc R . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O3 C8 117.30(14) . . ?
C16 O4 C17 116.48(15) . . ?
C2 C3 C4 119.64(16) . . ?
C2 C3 C7 119.34(15) . . ?
C4 C3 C7 120.99(15) . . ?
C2 C20 H20A 109.5 . . ?
C2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C2 N1 C6 119.39(16) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C5 C4 119.66(16) . . ?
C6 C5 C16 119.20(16) . . ?
C4 C5 C16 121.12(17) . . ?
C3 C4 C5 117.37(16) . . ?
C3 C4 C10 121.19(15) . . ?
C5 C4 C10 121.44(15) . . ?
C11 C10 C15 118.72(18) . . ?
C11 C10 C4 121.16(15) . . ?
C15 C10 C4 120.12(17) . . ?
O2 C7 O3 124.28(17) . . ?
O2 C7 C3 124.29(16) . . ?
O3 C7 C3 111.41(14) . . ?
N1 C2 C3 122.10(16) . . ?
N1 C2 C20 115.55(16) . . ?
C3 C2 C20 122.34(16) . . ?
O4 C17 C18 111.10(19) . . ?
O4 C17 H17A 109.4 . . ?
C18 C17 H17A 109.4 . . ?
O4 C17 H17B 109.4 . . ?
C18 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
O1 C16 O4 123.68(18) . . ?
O1 C16 C5 124.82(18) . . ?
O4 C16 C5 111.48(15) . . ?
N1 C6 C5 121.75(17) . . ?
N1 C6 C19 115.09(18) . . ?
C5 C6 C19 123.13(18) . . ?
O3 C8 C9 111.72(18) . . ?
O3 C8 H8A 109.3 . . ?
C9 C8 H8A 109.3 . . ?
O3 C8 H8B 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
C14 C15 C10 119.6(2) . . ?
C14 C15 H15 120.2 . . ?
C10 C15 H15 120.2 . . ?
C12 C11 C10 120.78(18) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C13 C12 C11 120.4(2) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C13 C14 C15 120.81(19) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C14 C13 C12 119.7(2) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C6 C19 H19A 109.5 . . ?
C6 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C6 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C7 1.330(2) . ?
O3 C8 1.457(2) . ?
O4 C16 1.333(2) . ?
O4 C17 1.460(2) . ?
C3 C2 1.396(3) . ?
C3 C4 1.400(2) . ?
C3 C7 1.498(2) . ?
C20 C2 1.509(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
N1 C2 1.335(2) . ?
N1 C6 1.345(2) . ?
C9 C8 1.492(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
O2 C7 1.201(2) . ?
C5 C6 1.396(3) . ?
C5 C4 1.402(2) . ?
C5 C16 1.497(3) . ?
C4 C10 1.487(3) . ?
C10 C11 1.384(3) . ?
C10 C15 1.396(3) . ?
C17 C18 1.488(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
O1 C16 1.194(2) . ?
C6 C19 1.506(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C15 C14 1.392(3) . ?
C15 H15 0.9300 . ?
C11 C12 1.380(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.371(3) . ?
C12 H12 0.9300 . ?
C14 C13 1.369(3) . ?
C14 H14 0.9300 . ?
C13 H13 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C3 C4 C5 -1.5(2) . . . . ?
C7 C3 C4 C5 -179.71(15) . . . . ?
C2 C3 C4 C10 178.26(15) . . . . ?
C7 C3 C4 C10 0.1(2) . . . . ?
C6 C5 C4 C3 3.1(2) . . . . ?
C16 C5 C4 C3 -175.05(15) . . . . ?
C6 C5 C4 C10 -176.66(16) . . . . ?
C16 C5 C4 C10 5.2(2) . . . . ?
C3 C4 C10 C11 57.8(2) . . . . ?
C5 C4 C10 C11 -122.47(19) . . . . ?
C3 C4 C10 C15 -122.01(19) . . . . ?
C5 C4 C10 C15 57.8(2) . . . . ?
C8 O3 C7 O2 1.7(3) . . . . ?
C8 O3 C7 C3 179.96(15) . . . . ?
C2 C3 C7 O2 68.9(3) . . . . ?
C4 C3 C7 O2 -112.9(2) . . . . ?
C2 C3 C7 O3 -109.40(18) . . . . ?
C4 C3 C7 O3 68.8(2) . . . . ?
C6 N1 C2 C3 2.3(3) . . . . ?
C6 N1 C2 C20 -178.51(16) . . . . ?
C4 C3 C2 N1 -1.2(3) . . . . ?
C7 C3 C2 N1 177.01(15) . . . . ?
C4 C3 C2 C20 179.65(16) . . . . ?
C7 C3 C2 C20 -2.1(3) . . . . ?
C16 O4 C17 C18 81.4(2) . . . . ?
C17 O4 C16 O1 3.2(3) . . . . ?
C17 O4 C16 C5 -178.15(17) . . . . ?
C6 C5 C16 O1 63.1(3) . . . . ?
C4 C5 C16 O1 -118.7(2) . . . . ?
C6 C5 C16 O4 -115.54(19) . . . . ?
C4 C5 C16 O4 62.6(2) . . . . ?
C2 N1 C6 C5 -0.6(3) . . . . ?
C2 N1 C6 C19 177.38(17) . . . . ?
C4 C5 C6 N1 -2.2(3) . . . . ?
C16 C5 C6 N1 176.04(16) . . . . ?
C4 C5 C6 C19 -179.97(17) . . . . ?
C16 C5 C6 C19 -1.8(3) . . . . ?
C7 O3 C8 C9 81.2(2) . . . . ?
C11 C10 C15 C14 0.9(3) . . . . ?
C4 C10 C15 C14 -179.29(18) . . . . ?
C15 C10 C11 C12 -1.1(3) . . . . ?
C4 C10 C11 C12 179.10(17) . . . . ?
C10 C11 C12 C13 0.8(3) . . . . ?
C10 C15 C14 C13 -0.5(3) . . . . ?
C15 C14 C13 C12 0.1(4) . . . . ?
C11 C12 C13 C14 -0.3(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 547037
