#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/73/2217326.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_2217326
loop_
_publ_author_name
'Fei Teng'
'Fanpeng Kong'
'Qingjian Liu'
_publ_section_title
;
 Dimethyl
 4-(4-formylphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
;
_journal_coeditor_code           SQ2008
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o293
_journal_page_last               o293
_journal_paper_doi               10.1107/S1600536807063428
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C18 H19 N O5'
_chemical_formula_moiety         'C18 H19 N O5'
_chemical_formula_structural     'C18 H19 N O5'
_chemical_formula_sum            'C18 H19 N O5'
_chemical_formula_weight         329.34
_chemical_melting_point          479
_chemical_name_systematic
;Dimethyl
 4-(4-formylphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
;
_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
_cell_angle_alpha                111.364(3)
_cell_angle_beta                 102.799(3)
_cell_angle_gamma                101.150(4)
_cell_formula_units_Z            2
_cell_length_a                   8.219(2)
_cell_length_b                   10.432(3)
_cell_length_c                   10.979(3)
_cell_measurement_reflns_used    1572
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.692
_cell_measurement_theta_min      2.199
_cell_volume                     815.0(4)
_computing_cell_refinement       'SMART (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2001)'
_computing_publication_material  'SHELXTL (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'phi and omega 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  0.0149
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.9902
_exptl_absorpt_correction_T_min  0.9543
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS: Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.229
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2855
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0519
_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)+(0.0745P)²+0.2263P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1331
_refine_ls_wR_factor_ref         0.1402
_reflns_number_gt                2352
_reflns_number_total             2855
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            sq2008.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2217326
_cod_database_fobs_code          2217326
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
C C1 0.0487(3) 0.7111(3) 0.2379(2) 0.0540(6) Uani d . 1
H H1A 0.1663 0.7527 0.2429 0.081 Uiso calc R 1
H H1B -0.0263 0.7598 0.2053 0.081 Uiso calc R 1
H H1C 0.0087 0.6105 0.1753 0.081 Uiso calc R 1
C C2 0.1597(3) 0.6835(2) 0.4429(2) 0.0369(5) Uani d . 1
C C3 0.1430(2) 0.7146(2) 0.58051(19) 0.0316(4) Uani d . 1
C C4 0.2082(3) 0.6488(2) 0.6575(2) 0.0360(5) Uani d . 1
C C5 0.3136(3) 0.5473(2) 0.6249(3) 0.0501(6) Uani d . 1
H H5A 0.2939 0.5048 0.5272 0.075 Uiso calc R 1
H H5B 0.2792 0.4727 0.6538 0.075 Uiso calc R 1
H H5C 0.4355 0.5989 0.6725 0.075 Uiso calc R 1
C C6 -0.0172(3) 0.7028(3) 0.9224(3) 0.0562(6) Uani d . 1
H H6A -0.0266 0.7913 0.9853 0.084 Uiso calc R 1
H H6B 0.0693 0.6730 0.9707 0.084 Uiso calc R 1
H H6C -0.1282 0.6294 0.8845 0.084 Uiso calc R 1
C C7 0.0357(3) 0.7258(2) 0.8083(2) 0.0369(5) Uani d . 1
C C8 -0.0337(2) 0.7922(2) 0.73481(19) 0.0326(4) Uani d . 1
C C9 -0.1879(3) 0.8380(2) 0.7515(2) 0.0403(5) Uani d . 1
C C10 -0.3909(3) 0.9447(3) 0.6724(3) 0.0648(7) Uani d . 1
H H10A -0.4883 0.8609 0.6436 0.097 Uiso calc R 1
H H10B -0.4126 0.9901 0.6110 0.097 Uiso calc R 1
H H10C -0.3759 1.0113 0.7646 0.097 Uiso calc R 1
C C11 0.0538(2) 0.8272(2) 0.63858(18) 0.0298(4) Uani d . 1
H H11 -0.0369 0.8235 0.5614 0.036 Uiso calc R 1
C C12 0.1873(2) 0.9776(2) 0.70850(19) 0.0306(4) Uani d . 1
C C13 0.2279(3) 1.0506(2) 0.6300(2) 0.0352(5) Uani d . 1
H H13 0.1695 1.0093 0.5356 0.042 Uiso calc R 1
C C14 0.3539(3) 1.1837(2) 0.6906(2) 0.0387(5) Uani d . 1
H H14 0.3797 1.2310 0.6368 0.046 Uiso calc R 1
C C15 0.4421(2) 1.2473(2) 0.8316(2) 0.0360(5) Uani d . 1
C C16 0.5802(3) 1.3855(2) 0.8933(2) 0.0443(5) Uani d . 1
H H16 0.5943 1.4329 0.8374 0.053 Uiso calc R 1
C C17 0.4002(3) 1.1764(2) 0.9107(2) 0.0423(5) Uani d . 1
H H17 0.4576 1.2186 1.0054 0.051 Uiso calc R 1
C C18 0.2739(3) 1.0439(2) 0.8499(2) 0.0395(5) Uani d . 1
H H18 0.2461 0.9981 0.9044 0.047 Uiso calc R 1
O O1 0.2601(3) 0.6284(2) 0.39502(18) 0.0686(5) Uani d . 1
O O2 0.0449(2) 0.72623(17) 0.37188(14) 0.0483(4) Uani d . 1
O O3 -0.23540(19) 0.90263(18) 0.66944(17) 0.0504(4) Uani d . 1
O O4 -0.2703(2) 0.8207(2) 0.8252(2) 0.0747(6) Uani d . 1
O O5 0.6775(2) 1.44321(17) 1.01131(17) 0.0562(5) Uani d . 1
N N1 0.1702(2) 0.67213(19) 0.77876(18) 0.0412(4) Uani d . 1
H H1 0.2335 0.6523 0.8389 0.049 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_
_diffrn_reflns_number
4173
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
O2 C1 H1A 109.5 n
O2 C1 H1B 109.5 n
H1A C1 H1B 109.5 n
O2 C1 H1C 109.5 n
H1A C1 H1C 109.5 n
H1B C1 H1C 109.5 n
O1 C2 O2 121.76(19) n
O1 C2 C3 127.5(2) n
O2 C2 C3 110.72(16) n
C4 C3 C2 121.94(18) n
C4 C3 C11 119.60(17) y
C2 C3 C11 118.44(16) n
C3 C4 N1 118.15(18) y
C3 C4 C5 127.55(19) n
N1 C4 C5 114.27(17) n
C4 C5 H5A 109.5 n
C4 C5 H5B 109.5 n
H5A C5 H5B 109.5 n
C4 C5 H5C 109.5 n
H5A C5 H5C 109.5 n
H5B C5 H5C 109.5 n
C7 C6 H6A 109.5 n
C7 C6 H6B 109.5 n
H6A C6 H6B 109.5 n
C7 C6 H6C 109.5 n
H6A C6 H6C 109.5 n
H6B C6 H6C 109.5 n
C8 C7 N1 118.71(17) y
C8 C7 C6 126.71(19) n
N1 C7 C6 114.59(18) n
C7 C8 C9 121.16(17) n
C7 C8 C11 119.69(17) y
C9 C8 C11 119.07(16) n
O4 C9 O3 121.06(19) n
O4 C9 C8 127.2(2) n
O3 C9 C8 111.71(16) n
O3 C10 H10A 109.5 n
O3 C10 H10B 109.5 n
H10A C10 H10B 109.5 n
O3 C10 H10C 109.5 n
H10A C10 H10C 109.5 n
H10B C10 H10C 109.5 n
C8 C11 C3 110.09(15) y
C8 C11 C12 112.69(15) y
C3 C11 C12 109.55(15) y
C8 C11 H11 108.1 n
C3 C11 H11 108.1 n
C12 C11 H11 108.1 n
C18 C12 C13 118.16(18) n
C18 C12 C11 121.69(16) n
C13 C12 C11 120.14(16) n
C14 C13 C12 120.86(18) n
C14 C13 H13 119.6 n
C12 C13 H13 119.6 n
C13 C14 C15 120.34(18) n
C13 C14 H14 119.8 n
C15 C14 H14 119.8 n
C17 C15 C14 119.14(19) n
C17 C15 C16 121.20(19) n
C14 C15 C16 119.65(19) n
O5 C16 C15 125.3(2) n
O5 C16 H16 117.4 n
C15 C16 H16 117.4 n
C18 C17 C15 120.34(19) n
C18 C17 H17 119.8 n
C15 C17 H17 119.8 n
C17 C18 C12 121.13(18) n
C17 C18 H18 119.4 n
C12 C18 H18 119.4 n
C2 O2 C1 118.39(17) n
C9 O3 C10 116.16(17) n
C7 N1 C4 123.31(16) y
C7 N1 H1 118.3 n
C4 N1 H1 118.3 n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O2 1.429(2) n
C1 H1A 0.9600 n
C1 H1B 0.9600 n
C1 H1C 0.9600 n
C2 O1 1.202(2) n
C2 O2 1.337(3) n
C2 C3 1.469(3) n
C3 C4 1.355(3) y
C3 C11 1.522(3) y
C4 N1 1.381(3) y
C4 C5 1.489(3) n
C5 H5A 0.9600 n
C5 H5B 0.9600 n
C5 H5C 0.9600 n
C6 C7 1.495(3) n
C6 H6A 0.9600 n
C6 H6B 0.9600 n
C6 H6C 0.9600 n
C7 C8 1.346(3) y
C7 N1 1.381(3) y
C8 C9 1.463(3) n
C8 C11 1.511(2) y
C9 O4 1.203(2) n
C9 O3 1.344(2) n
C10 O3 1.432(3) n
C10 H10A 0.9600 n
C10 H10B 0.9600 n
C10 H10C 0.9600 n
C11 C12 1.529(3) n
C11 H11 0.9800 n
C12 C18 1.390(3) n
C12 C13 1.394(3) n
C13 C14 1.381(3) n
C13 H13 0.9300 n
C14 C15 1.389(3) n
C14 H14 0.9300 n
C15 C17 1.386(3) n
C15 C16 1.463(3) n
C16 O5 1.211(3) n
C16 H16 0.9300 n
C17 C18 1.378(3) n
C17 H17 0.9300 n
C18 H18 0.9300 n
N1 H1 0.8600 n
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 O5 2_677 0.86 2.27 3.107(2) 163.0
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
O1 C2 C3 C4 -18.6(3) y
O2 C2 C3 C4 161.80(17) n
O1 C2 C3 C11 159.8(2) n
O2 C2 C3 C11 -19.8(2) n
C2 C3 C4 N1 -172.96(17) n
C11 C3 C4 N1 8.7(3) y
C2 C3 C4 C5 4.6(3) n
C11 C3 C4 C5 -173.75(19) n
N1 C7 C8 C9 173.70(18) n
C6 C7 C8 C9 -6.5(3) n
N1 C7 C8 C11 -9.5(3) y
C6 C7 C8 C11 170.29(19) n
C7 C8 C9 O4 -1.9(3) y
C11 C8 C9 O4 -178.8(2) n
C7 C8 C9 O3 179.69(18) n
C11 C8 C9 O3 2.8(3) n
C7 C8 C11 C3 31.4(2) y
C9 C8 C11 C3 -151.73(17) n
C7 C8 C11 C12 -91.2(2) n
C9 C8 C11 C12 85.7(2) n
C4 C3 C11 C8 -31.0(2) y
C2 C3 C11 C8 150.61(16) n
C4 C3 C11 C12 93.5(2) n
C2 C3 C11 C12 -84.9(2) n
C8 C11 C12 C18 27.1(2) y
C3 C11 C12 C18 -95.8(2) n
C8 C11 C12 C13 -154.35(17) n
C3 C11 C12 C13 82.7(2) n
C18 C12 C13 C14 1.6(3) n
C11 C12 C13 C14 -177.05(17) n
C12 C13 C14 C15 -0.2(3) n
C13 C14 C15 C17 -1.0(3) n
C13 C14 C15 C16 177.53(18) n
C17 C15 C16 O5 6.6(3) n
C14 C15 C16 O5 -171.9(2) n
C14 C15 C17 C18 0.7(3) n
C16 C15 C17 C18 -177.79(19) n
C15 C17 C18 C12 0.7(3) n
C13 C12 C18 C17 -1.8(3) n
C11 C12 C18 C17 176.73(18) n
O1 C2 O2 C1 -2.8(3) n
C3 C2 O2 C1 176.83(18) n
O4 C9 O3 C10 -1.8(3) n
C8 C9 O3 C10 176.73(19) n
C8 C7 N1 C4 -17.3(3) n
C6 C7 N1 C4 162.9(2) n
C3 C4 N1 C7 17.6(3) n
C5 C4 N1 C7 -160.32(19) n
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21119467
