#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:16:01 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180069 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/15/7051556.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_7051556
loop_
_publ_author_name
'Suárez, Margarita'
'de Armas, Merly'
'Ramírez, Oney'
'Alvarez, Amaury'
'Martínez-Alvarez, Roberto'
'Molero, Dolores'
'Seoane, Carlos'
'Liz, Ramón'
'de Armas, Hector Novoa'
'Blaton, Norbert M.'
'Peeters, Oswald M.'
'Martín, Nazario'
_publ_section_title
;
 Synthesis and structural study of new highly lipophilic
 1,4-dihydropyridines
;
_journal_issue                   12
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1567
_journal_paper_doi               10.1039/b506018d
_journal_volume                  29
_journal_year                    2005
_chemical_formula_sum            'C32 H50 N2 O4'
_chemical_formula_weight         526.74
_chemical_name_common
;3-Decyl-5-octyl 2,6-dimethyl-4-(3'-pyridyl)-1,4-dihydropyridine-
3,5-dicarboxylate
;
_chemical_name_systematic
;
3-Decyl-5-octyl 2,6-dimethyl-4-(3'-pyridyl)-1,4-dihydropyridine-3,5-dicarboxylate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.021(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.8754(7)
_cell_length_b                   16.1015(12)
_cell_length_c                   8.7774(16)
_cell_measurement_reflns_used    35
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.25
_cell_measurement_theta_min      9.02
_cell_volume                     3233.0(6)
_computing_cell_refinement       'XSCANS (Siemens, 1996)'
_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_data_reduction        'XSCANS (Siemens, 1996)'
_computing_molecular_graphics    'DIAMOND (Bergerhoff, 1996)'
_computing_publication_material  'PARST (Nardelli, 1983)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al, 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.947
_diffrn_measured_fraction_theta_max 0.947
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_av_sigmaI/netI    0.1061
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            7434
_diffrn_reflns_theta_full        69.05
_diffrn_reflns_theta_max         69.05
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    0.553
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.082
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.00027(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         5718
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.968
_refine_ls_R_factor_all          0.2475
_refine_ls_R_factor_gt           0.0856
_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)+(0.1440P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2182
_refine_ls_wR_factor_ref         0.3405
_reflns_number_gt                1522
_reflns_number_total             5718
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b506018d.txt
_cod_data_source_block           dhp5_2
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7051556
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.1129(2) 0.0736(3) -0.0844(5) 0.0772(14) Uani 1 1 d . . .
H1 H 0.0936 0.0922 -0.1612 0.096 Uiso 1 1 calc R . .
C2 C 0.1604(3) 0.1189(4) -0.0315(6) 0.0722(17) Uani 1 1 d . . .
C21 C 0.1823(3) 0.1824(4) -0.1426(6) 0.090(2) Uani 1 1 d . . .
H21A H 0.1848 0.2355 -0.0933 0.134 Uiso 1 1 calc R . .
H21B H 0.1560 0.1859 -0.2274 0.134 Uiso 1 1 calc R . .
H21C H 0.2204 0.1665 -0.1782 0.134 Uiso 1 1 calc R . .
C3 C 0.1813(3) 0.1033(3) 0.1072(6) 0.0648(15) Uani 1 1 d . . .
C7 C 0.2353(3) 0.1408(4) 0.1639(6) 0.0711(16) Uani 1 1 d . . .
O8 O 0.2660(2) 0.1896(3) 0.0946(5) 0.1044(16) Uani 1 1 d . . .
O33 O 0.24905(17) 0.1162(2) 0.3044(4) 0.0761(12) Uani 1 1 d . . .
C34 C 0.3029(3) 0.1473(4) 0.3695(6) 0.0825(19) Uani 1 1 d . . .
H34A H 0.3019 0.2075 0.3738 0.103 Uiso 1 1 calc R . .
H34B H 0.3358 0.1310 0.3063 0.103 Uiso 1 1 calc R . .
C35 C 0.3101(3) 0.1129(4) 0.5254(7) 0.089(2) Uani 1 1 d . . .
H35A H 0.3118 0.0528 0.5188 0.111 Uiso 1 1 calc R . .
H35B H 0.2760 0.1273 0.5854 0.111 Uiso 1 1 calc R . .
C36 C 0.3635(3) 0.1433(4) 0.6059(7) 0.093(2) Uani 1 1 d . . .
H36A H 0.3973 0.1289 0.5448 0.116 Uiso 1 1 calc R . .
H36B H 0.3616 0.2034 0.6109 0.116 Uiso 1 1 calc R . .
C37 C 0.3729(3) 0.1111(5) 0.7626(7) 0.101(2) Uani 1 1 d . . .
H37A H 0.3768 0.0512 0.7571 0.126 Uiso 1 1 calc R . .
H37B H 0.3383 0.1230 0.8225 0.126 Uiso 1 1 calc R . .
C38 C 0.4254(3) 0.1455(5) 0.8458(8) 0.113(3) Uani 1 1 d . . .
H38A H 0.4599 0.1350 0.7844 0.142 Uiso 1 1 calc R . .
H38B H 0.4209 0.2053 0.8534 0.142 Uiso 1 1 calc R . .
C39 C 0.4362(4) 0.1122(6) 1.0014(8) 0.130(3) Uani 1 1 d . . .
H39A H 0.4407 0.0524 0.9941 0.162 Uiso 1 1 calc R . .
H39B H 0.4019 0.1230 1.0633 0.162 Uiso 1 1 calc R . .
C310 C 0.4884(4) 0.1465(7) 1.0818(9) 0.163(4) Uani 1 1 d . B .
H31A H 0.4839 0.2063 1.0897 0.204 Uiso 1 1 calc R . .
H31B H 0.5227 0.1359 1.0198 0.204 Uiso 1 1 calc R . .
C311 C 0.4994(5) 0.1118(8) 1.2407(11) 0.198(5) Uani 1 1 d . . .
H31C H 0.4655 0.1207 1.3029 0.248 Uiso 1 1 calc R A 1
H31D H 0.5072 0.0533 1.2338 0.248 Uiso 1 1 calc R A 1
H31J H 0.5324 0.1394 1.2854 0.248 Uiso 0.50 1 calc R C 2
C312 C 0.5497(10) 0.1469(19) 1.320(2) 0.210(12) Uani 0.50 1 d P B 1
H31E H 0.5424 0.2057 1.3350 0.262 Uiso 0.50 1 calc PR B 1
H31F H 0.5833 0.1422 1.2530 0.262 Uiso 0.50 1 calc PR B 1
C313 C 0.566(3) 0.108(4) 1.477(4) 0.49(5) Uani 0.50 1 d P B 1
H31G H 0.6063 0.1214 1.5001 0.737 Uiso 0.50 1 calc PR B 1
H31H H 0.5616 0.0491 1.4725 0.737 Uiso 0.50 1 calc PR B 1
H31I H 0.5414 0.1307 1.5545 0.737 Uiso 0.50 1 calc PR B 1
C4 C 0.1498(2) 0.0422(3) 0.2147(6) 0.0644(15) Uani 1 1 d . . .
H4 H 0.1795 0.0114 0.2721 0.080 Uiso 1 1 calc R . .
C1' C 0.1105(2) 0.0884(3) 0.3291(5) 0.0620(15) Uani 1 1 d . . .
C2' C 0.1156(3) 0.0738(4) 0.4822(6) 0.0834(19) Uani 1 1 d . . .
H42 H 0.1445 0.0371 0.5142 0.104 Uiso 1 1 calc R . .
N3' N 0.0817(3) 0.1085(4) 0.5891(5) 0.0935(17) Uani 1 1 d . . .
C4' C 0.0411(3) 0.1617(4) 0.5419(7) 0.088(2) Uani 1 1 d . . .
H44 H 0.0165 0.1857 0.6136 0.110 Uiso 1 1 calc R . .
C5' C 0.0341(3) 0.1824(4) 0.3913(7) 0.0818(19) Uani 1 1 d . . .
H45 H 0.0062 0.2213 0.3627 0.102 Uiso 1 1 calc R . .
C6' C 0.0688(3) 0.1451(4) 0.2829(6) 0.0750(17) Uani 1 1 d . . .
H46 H 0.0642 0.1579 0.1802 0.094 Uiso 1 1 calc R . .
C5 C 0.1141(2) -0.0195(4) 0.1236(6) 0.0667(15) Uani 1 1 d . . .
C9 C 0.1022(3) -0.1000(4) 0.1940(8) 0.0792(18) Uani 1 1 d . . .
O10 O 0.0694(2) -0.1543(3) 0.1492(5) 0.1140(17) Uani 1 1 d . . .
O53 O 0.1321(2) -0.1090(3) 0.3242(5) 0.0959(14) Uani 1 1 d . . .
C54 C 0.1267(4) -0.1862(4) 0.4071(9) 0.113(3) Uani 1 1 d . . .
H54A H 0.1290 -0.2329 0.3376 0.141 Uiso 1 1 calc R . .
H54B H 0.0894 -0.1884 0.4594 0.141 Uiso 1 1 calc R . .
C55 C 0.1747(6) -0.1894(7) 0.5173(14) 0.205(6) Uani 1 1 d . . .
H55A H 0.1621 -0.2304 0.5912 0.256 Uiso 1 1 calc R . .
H55B H 0.2064 -0.2155 0.4615 0.256 Uiso 1 1 calc R . .
C56 C 0.2001(6) -0.1337(7) 0.5978(14) 0.180(5) Uani 1 1 d . . .
H56A H 0.1691 -0.1072 0.6552 0.225 Uiso 1 1 calc R . .
H56B H 0.2136 -0.0925 0.5252 0.225 Uiso 1 1 calc R . .
C57 C 0.2496(6) -0.1436(7) 0.7091(15) 0.199(5) Uani 1 1 d . . .
H57A H 0.2478 -0.2001 0.7476 0.248 Uiso 1 1 calc R . .
H57B H 0.2856 -0.1390 0.6517 0.248 Uiso 1 1 calc R . .
C58 C 0.2546(7) -0.0928(9) 0.8315(16) 0.204(6) Uani 1 1 d . . .
H58A H 0.2165 -0.0911 0.8798 0.255 Uiso 1 1 calc R . .
H58B H 0.2620 -0.0375 0.7922 0.255 Uiso 1 1 calc R . .
C59 C 0.2978(7) -0.1075(11) 0.9537(17) 0.230(7) Uani 1 1 d . . .
H59A H 0.3012 -0.1675 0.9588 0.287 Uiso 1 1 calc R . .
H59B H 0.3345 -0.0883 0.9107 0.287 Uiso 1 1 calc R . .
C510 C 0.2999(9) -0.0854(12) 1.086(2) 0.277(9) Uani 1 1 d . D .
H51A H 0.2621 -0.1008 1.1272 0.346 Uiso 1 1 calc R . .
H51B H 0.2997 -0.0252 1.0808 0.346 Uiso 1 1 calc R . .
C511 C 0.3417(8) -0.1047(12) 1.2100(18) 0.239(7) Uani 1 1 d D . .
H51C H 0.3772 -0.0740 1.1945 0.299 Uiso 1 1 calc R C 2
H51D H 0.3249 -0.0896 1.3062 0.299 Uiso 1 1 calc R C 2
H51J H 0.3502 -0.1631 1.2095 0.299 Uiso 0.50 1 calc R C 2
C512 C 0.3785(19) -0.153(2) 1.317(6) 0.52(5) Uani 0.50 1 d PD D 2
H51E H 0.4007 -0.1938 1.2607 0.655 Uiso 0.50 1 calc PR D 2
H51F H 0.3538 -0.1815 1.3891 0.655 Uiso 0.50 1 calc PR D 2
C513 C 0.419(2) -0.097(3) 1.400(6) 0.84(15) Uani 0.50 1 d PD D 2
H51G H 0.4401 -0.1279 1.4760 1.253 Uiso 0.50 1 calc PR D 2
H51H H 0.3975 -0.0530 1.4485 1.253 Uiso 0.50 1 calc PR D 2
H51I H 0.4467 -0.0729 1.3296 1.253 Uiso 0.50 1 calc PR D 2
C6 C 0.0953(3) -0.0011(4) -0.0181(7) 0.0760(17) Uani 1 1 d . . .
C61 C 0.0552(3) -0.0516(4) -0.1184(6) 0.094(2) Uani 1 1 d . . .
H61A H 0.0537 -0.1077 -0.0816 0.141 Uiso 1 1 calc R . .
H61B H 0.0698 -0.0513 -0.2209 0.141 Uiso 1 1 calc R . .
H61C H 0.0167 -0.0280 -0.1164 0.141 Uiso 1 1 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C2 N1 C6 122.7(5) . . ?
C3 C2 N1 119.2(5) . . ?
C3 C2 C21 127.0(6) . . ?
N1 C2 C21 113.8(5) . . ?
C2 C3 C7 122.5(5) . . ?
C2 C3 C4 120.7(5) . . ?
C7 C3 C4 116.8(5) . . ?
O8 C7 O33 121.2(6) . . ?
O8 C7 C3 125.8(6) . . ?
O33 C7 C3 113.0(6) . . ?
C7 O33 C34 117.6(5) . . ?
O33 C34 C35 109.1(5) . . ?
C34 C35 C36 113.8(6) . . ?
C37 C36 C35 116.2(6) . . ?
C36 C37 C38 115.8(6) . . ?
C39 C38 C37 116.3(7) . . ?
C38 C39 C310 115.6(8) . . ?
C39 C310 C311 115.4(10) . . ?
C312 C311 C310 115.0(15) . . ?
C311 C312 C313 117(3) . . ?
C5 C4 C1' 110.3(4) . . ?
C5 C4 C3 110.4(4) . . ?
C1' C4 C3 111.3(4) . . ?
C2' C1' C6' 117.4(5) . . ?
C2' C1' C4 120.5(5) . . ?
C6' C1' C4 122.1(5) . . ?
N3' C2' C1' 124.6(6) . . ?
C4' N3' C2' 117.0(5) . . ?
N3' C4' C5' 122.5(6) . . ?
C4' C5' C6' 119.6(6) . . ?
C5' C6' C1' 118.9(5) . . ?
C6 C5 C9 121.7(6) . . ?
C6 C5 C4 121.0(5) . . ?
C9 C5 C4 117.3(5) . . ?
O10 C9 O53 120.9(6) . . ?
O10 C9 C5 128.0(7) . . ?
O53 C9 C5 111.1(6) . . ?
C9 O53 C54 118.5(6) . . ?
O53 C54 C55 107.3(6) . . ?
C56 C55 C54 132.8(12) . . ?
C55 C56 C57 128.7(12) . . ?
C58 C57 C56 120.9(14) . . ?
C57 C58 C59 122.3(15) . . ?
C510 C59 C58 132.2(19) . . ?
C59 C510 C511 132(2) . . ?
C512 C511 C510 161(2) . . ?
C511 C512 C513 110.7(19) . . ?
C5 C6 N1 118.8(6) . . ?
C5 C6 C61 127.8(6) . . ?
N1 C6 C61 113.4(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
N1 C2 1.388(7) . ?
N1 C6 1.395(7) . ?
C2 C3 1.333(7) . ?
C2 C21 1.500(7) . ?
C3 C7 1.461(8) . ?
C3 C4 1.543(7) . ?
C7 O8 1.216(6) . ?
C7 O33 1.333(6) . ?
O33 C34 1.448(6) . ?
C34 C35 1.486(8) . ?
C35 C36 1.493(8) . ?
C36 C37 1.485(8) . ?
C37 C38 1.512(9) . ?
C38 C39 1.488(9) . ?
C39 C310 1.493(10) . ?
C310 C311 1.523(12) . ?
C311 C312 1.46(2) . ?
C312 C313 1.56(4) . ?
C4 C5 1.514(7) . ?
C4 C1' 1.540(7) . ?
C1' C2' 1.369(7) . ?
C1' C6' 1.382(7) . ?
C2' N3' 1.338(7) . ?
N3' C4' 1.330(7) . ?
C4' C5' 1.372(7) . ?
C5' C6' 1.377(7) . ?
C5 C6 1.350(7) . ?
C5 C9 1.462(8) . ?
C9 O10 1.216(7) . ?
C9 O53 1.340(7) . ?
O53 C54 1.446(7) . ?
C54 C55 1.464(12) . ?
C55 C56 1.282(12) . ?
C56 C57 1.503(14) . ?
C57 C58 1.355(14) . ?
C58 C59 1.479(16) . ?
C59 C510 1.215(15) . ?
C510 C511 1.482(19) . ?
C511 C512 1.476(19) . ?
C512 C513 1.49(2) . ?
C6 C61 1.509(7) . ?
