#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:28:26 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201972 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/43/2104356.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_2104356
loop_
_publ_author_name
'Rathore, R. S.'
'Reddy, B. Palakshi'
'Vijayakumar, V.'
'Ragavan, R. Venkat'
'Narasimhamurthy, T.'
_publ_section_title
;
 Hantzsch 1,4-dihydropyridine esters and analogs: candidates for
 generating reproducible one-dimensional packing motifs
;
_journal_coeditor_code           EB5001
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              375
_journal_page_last               381
_journal_paper_doi               10.1107/S0108768109004832
_journal_volume                  65
_journal_year                    2009
_chemical_formula_moiety         'C17 H18 N2 O4'
_chemical_formula_sum            'C17 H18 N2 O4'
_chemical_formula_weight         314.33
_chemical_melting_point          483
_chemical_name_common            'Hantzsch 1,4-dihydropyridine ester analog'
_chemical_name_systematic
;
3, 5-diacetyl-2, 6-dimethyl -1, 4 dihydro-4-(3-nitrophenyl)-3, 5-pyridine
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 104.606(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8420(7)
_cell_length_b                   16.0785(14)
_cell_length_c                   11.2188(10)
_cell_measurement_reflns_used    1601
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      19.1
_cell_measurement_theta_min      2.3
_cell_volume                     1543.4(2)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        SAINT-Plus
_computing_molecular_graphics
'ORTEP-III (Farrugia, 1997), PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 and PLATON'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXTL (Bruker, 2003) '
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω-scans'
_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  0.0497
_diffrn_reflns_av_sigmaI/netI    0.0525
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11818
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.26
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.171
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3025
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.1063
_refine_ls_R_factor_gt           0.0646
_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)+(0.0354P)²+0.4210P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1264
_reflns_number_gt                2030
_reflns_number_total             3025
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            eb5001.cif
_cod_data_source_block           III
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               2104356
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_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
O O1 0.4112(2) 0.12566(11) 0.16606(15) 0.0564(5) Uani d . 1 . .
O O2 0.5779(2) 0.36297(11) -0.00143(16) 0.0659(6) Uani d . 1 . .
O O3 0.6369(3) 0.12095(16) -0.22215(19) 0.0897(8) Uani d . 1 . .
O O4 0.8667(3) 0.06884(16) -0.1976(2) 0.0985(8) Uani d . 1 . .
N N1 0.7526(2) 0.31151(13) 0.42101(17) 0.0442(5) Uani d . 1 . .
H H1 0.8169 0.3220 0.4908 0.053 Uiso calc R 1 . .
N N2 0.7685(4) 0.10566(16) -0.1587(2) 0.0658(7) Uani d . 1 . .
C C2 0.6619(3) 0.24154(15) 0.4126(2) 0.0402(6) Uani d . 1 . .
C C3 0.5843(3) 0.21367(14) 0.2991(2) 0.0363(6) Uani d . 1 . .
C C4 0.6194(3) 0.25303(14) 0.1858(2) 0.0360(6) Uani d . 1 . .
H H4 0.5212 0.2546 0.1214 0.043 Uiso calc R 1 . .
C C5 0.6768(3) 0.34194(14) 0.2089(2) 0.0362(6) Uani d . 1 . .
C C6 0.7481(3) 0.36661(15) 0.3249(2) 0.0399(6) Uani d . 1 . .
C C7 0.6660(3) 0.20488(17) 0.5371(2) 0.0554(7) Uani d . 1 . .
H H7A 0.5622 0.2039 0.5489 0.083 Uiso calc R 1 . .
H H7B 0.7321 0.2382 0.6003 0.083 Uiso calc R 1 . .
H H7C 0.7063 0.1492 0.5415 0.083 Uiso calc R 1 . .
C C8 0.8227(3) 0.44876(17) 0.3697(2) 0.0592(8) Uani d . 1 . .
H H8A 0.9047 0.4603 0.3299 0.089 Uiso calc R 1 . .
H H8B 0.8656 0.4464 0.4572 0.089 Uiso calc R 1 . .
H H8C 0.7455 0.4920 0.3505 0.089 Uiso calc R 1 . .
C C9 0.4705(3) 0.14626(15) 0.2741(2) 0.0415(6) Uani d . 1 . .
C C10 0.4149(3) 0.10003(18) 0.3718(2) 0.0583(8) Uani d . 1 . .
H H10A 0.3481 0.0550 0.3347 0.087 Uiso calc R 1 . .
H H10B 0.3577 0.1373 0.4112 0.087 Uiso calc R 1 . .
H H10C 0.5033 0.0783 0.4319 0.087 Uiso calc R 1 . .
C C11 0.6493(3) 0.39327(15) 0.0967(2) 0.0445(6) Uani d . 1 . .
C C12 0.7071(4) 0.48069(17) 0.0954(3) 0.0714(9) Uani d . 1 . .
H H12A 0.6862 0.5002 0.0120 0.107 Uiso calc R 1 . .
H H12B 0.8176 0.4822 0.1320 0.107 Uiso calc R 1 . .
H H12C 0.6545 0.5157 0.1415 0.107 Uiso calc R 1 . .
C C13 0.7352(3) 0.20074(14) 0.1369(2) 0.0356(6) Uani d . 1 . .
C C14 0.7014(3) 0.17810(15) 0.0138(2) 0.0415(6) Uani d . 1 . .
H H14 0.6073 0.1938 -0.0398 0.050 Uiso calc R 1 . .
C C15 0.8090(3) 0.13189(15) -0.0284(2) 0.0448(6) Uani d . 1 . .
C C16 0.9500(3) 0.10816(16) 0.0470(3) 0.0559(7) Uani d . 1 . .
H H16 1.0214 0.0777 0.0165 0.067 Uiso calc R 1 . .
C C17 0.9828(3) 0.13075(17) 0.1692(3) 0.0568(8) Uani d . 1 . .
H H17 1.0774 0.1152 0.2223 0.068 Uiso calc R 1 . .
C C18 0.8766(3) 0.17614(16) 0.2135(2) 0.0461(6) Uani d . 1 . .
H H18 0.9003 0.1905 0.2965 0.055 Uiso calc R 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
C2 N1 C6 . . 124.6(2) ?
C2 N1 H1 . . 117.7 ?
C6 N1 H1 . . 117.7 ?
O4 N2 O3 . . 123.1(3) ?
O4 N2 C15 . . 118.5(3) ?
O3 N2 C15 . . 118.4(3) ?
C3 C2 N1 . . 118.9(2) ?
C3 C2 C7 . . 128.8(2) ?
N1 C2 C7 . . 112.3(2) ?
C2 C3 C9 . . 125.9(2) ?
C2 C3 C4 . . 119.0(2) ?
C9 C3 C4 . . 115.1(2) ?
C5 C4 C3 . . 112.33(19) ?
C5 C4 C13 . . 110.70(19) ?
C3 C4 C13 . . 111.53(18) ?
C5 C4 H4 . . 107.3 ?
C3 C4 H4 . . 107.3 ?
C13 C4 H4 . . 107.3 ?
C6 C5 C11 . . 126.4(2) ?
C6 C5 C4 . . 119.6(2) ?
C11 C5 C4 . . 114.0(2) ?
C5 C6 N1 . . 118.3(2) ?
C5 C6 C8 . . 129.5(2) ?
N1 C6 C8 . . 112.1(2) ?
C2 C7 H7A . . 109.5 ?
C2 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C2 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C6 C8 H8A . . 109.5 ?
C6 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C6 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
O1 C9 C3 . . 119.3(2) ?
O1 C9 C10 . . 116.4(2) ?
C3 C9 C10 . . 124.3(2) ?
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 ?
O2 C11 C5 . . 118.8(2) ?
O2 C11 C12 . . 117.7(2) ?
C5 C11 C12 . . 123.4(2) ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C18 C13 C14 . . 118.5(2) ?
C18 C13 C4 . . 121.1(2) ?
C14 C13 C4 . . 120.4(2) ?
C15 C14 C13 . . 119.3(2) ?
C15 C14 H14 . . 120.4 ?
C13 C14 H14 . . 120.4 ?
C16 C15 C14 . . 122.3(2) ?
C16 C15 N2 . . 119.2(3) ?
C14 C15 N2 . . 118.5(3) ?
C15 C16 C17 . . 118.1(3) ?
C15 C16 H16 . . 121.0 ?
C17 C16 H16 . . 121.0 ?
C16 C17 C18 . . 120.5(3) ?
C16 C17 H17 . . 119.7 ?
C18 C17 H17 . . 119.7 ?
C17 C18 C13 . . 121.2(2) ?
C17 C18 H18 . . 119.4 ?
C13 C18 H18 . . 119.4 ?
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
O1 C9 . 1.238(3) ?
O2 C11 . 1.224(3) ?
O3 N2 . 1.226(3) ?
O4 N2 . 1.219(3) ?
N1 C2 . 1.371(3) ?
N1 C6 . 1.388(3) ?
N1 H1 . 0.8600 ?
N2 C15 . 1.476(3) ?
C2 C3 . 1.361(3) ?
C2 C7 . 1.508(3) ?
C3 C9 . 1.458(3) ?
C3 C4 . 1.520(3) ?
C4 C5 . 1.517(3) ?
C4 C13 . 1.529(3) ?
C4 H4 . 0.9800 ?
C5 C6 . 1.354(3) ?
C5 C11 . 1.473(3) ?
C6 C8 . 1.505(3) ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 C10 . 1.506(3) ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 C12 . 1.497(4) ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C13 C18 . 1.384(3) ?
C13 C14 . 1.387(3) ?
C14 C15 . 1.382(3) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.373(4) ?
C16 C17 . 1.376(4) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.377(3) ?
C17 H17 . 0.9300 ?
C18 H18 . 0.9300 ?
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
_geom_hbond_publ_flag
N1 H1 O1 4_555 0.86 2.11 2.933(3) 160 y
C18 H18 O2 4_555 0.93 2.56 3.305(3) 137 y
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 N1 C2 C3 . . . . 13.8(4) y
C6 N1 C2 C7 . . . . -167.2(2) ?
N1 C2 C3 C9 . . . . -172.9(2) ?
C7 C2 C3 C9 . . . . 8.3(4) ?
N1 C2 C3 C4 . . . . 8.9(3) y
C7 C2 C3 C4 . . . . -169.9(2) ?
C2 C3 C4 C5 . . . . -26.9(3) y
C9 C3 C4 C5 . . . . 154.7(2) ?
C2 C3 C4 C13 . . . . 98.1(2) y
C9 C3 C4 C13 . . . . -80.3(2) ?
C3 C4 C5 C6 . . . . 25.5(3) y
C13 C4 C5 C6 . . . . -99.9(2) ?
C3 C4 C5 C11 . . . . -155.4(2) ?
C13 C4 C5 C11 . . . . 79.2(2) ?
C11 C5 C6 N1 . . . . 174.9(2) ?
C4 C5 C6 N1 . . . . -6.2(3) y
C11 C5 C6 C8 . . . . -2.9(4) ?
C4 C5 C6 C8 . . . . 176.0(2) ?
C2 N1 C6 C5 . . . . -15.3(4) y
C2 N1 C6 C8 . . . . 162.9(2) ?
C2 C3 C9 O1 . . . . -178.2(2) y
C4 C3 C9 O1 . . . . 0.1(3) ?
C2 C3 C9 C10 . . . . 3.5(4) y
C4 C3 C9 C10 . . . . -178.2(2) ?
C6 C5 C11 O2 . . . . -177.4(2) y
C4 C5 C11 O2 . . . . 3.7(3) ?
C6 C5 C11 C12 . . . . 3.9(4) y
C4 C5 C11 C12 . . . . -175.0(2) ?
C5 C4 C13 C18 . . . . 73.3(3) ?
C3 C4 C13 C18 . . . . -52.5(3) ?
C5 C4 C13 C14 . . . . -105.6(2) ?
C3 C4 C13 C14 . . . . 128.6(2) y
C18 C13 C14 C15 . . . . 0.1(3) ?
C4 C13 C14 C15 . . . . 179.0(2) ?
C13 C14 C15 C16 . . . . -0.8(4) ?
C13 C14 C15 N2 . . . . 177.7(2) ?
O4 N2 C15 C16 . . . . -5.4(4) ?
O3 N2 C15 C16 . . . . 173.6(3) ?
O4 N2 C15 C14 . . . . 176.0(2) ?
O3 N2 C15 C14 . . . . -4.9(4) y
C14 C15 C16 C17 . . . . 0.9(4) ?
N2 C15 C16 C17 . . . . -177.6(2) ?
C15 C16 C17 C18 . . . . -0.2(4) ?
C16 C17 C18 C13 . . . . -0.4(4) ?
C14 C13 C18 C17 . . . . 0.5(4) ?
C4 C13 C18 C17 . . . . -178.4(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 254625
