#------------------------------------------------------------------------------
#$Date: 2017-10-14 21:27:35 +0200 (Sat 14 de Oct de 2017) $
#$Revision: 202017 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/19/7151933.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_7151933
loop_
_publ_author_name
'Jiang, Huanfeng'
'Ji, Xiaochen'
'Li, Yibiao'
'Chen, Zhengwang'
'Wang, Azhong'
_publ_section_title
;
 Palladium-assisted multicomponent cyclization of aromatic aldehydes,
 arylamines and terminal olefins under molecular oxygen: an assembly of
 1,4-dihydropyridines.
;
_journal_issue                   15
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5358
_journal_page_last               5361
_journal_paper_doi               10.1039/c1ob05440f
_journal_volume                  9
_journal_year                    2011
_chemical_formula_moiety         'C21 H19 N O4'
_chemical_formula_sum            'C21 H19 N O4'
_chemical_formula_weight         349.37
_chemical_name_systematic
;
?
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 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                 102.32(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.404(4)
_cell_length_b                   8.0536(16)
_cell_length_c                   11.589(2)
_cell_measurement_reflns_used    2895
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.89
_cell_measurement_theta_min      2.35
_cell_volume                     1769.3(6)
_computing_cell_refinement       RAPID-AUTO
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       ω
_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  0.0379
_diffrn_reflns_av_sigmaI/netI    0.0566
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6916
_diffrn_reflns_theta_full        25.20
_diffrn_reflns_theta_max         25.20
_diffrn_reflns_theta_min         3.16
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Jacobson, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.9(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3102
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.132
_refine_ls_R_factor_all          0.1056
_refine_ls_R_factor_gt           0.0401
_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)+(0.0443P)²+0.5456P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0815
_refine_ls_wR_factor_ref         0.1257
_reflns_number_gt                1742
_reflns_number_total             3102
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ob05440f.txt
_cod_data_source_block           1
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_Hall     'C -2yc '
_cod_original_sg_symbol_H-M      'C c '
_cod_database_code               7151933
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, 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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7038(2) 0.2194(5) 0.7941(4) 0.0490(10) Uani 1 1 d . . .
C2 C 0.73468(18) 0.2662(5) 0.6938(3) 0.0430(9) Uani 1 1 d . . .
C3 C 0.69469(19) 0.2800(5) 0.5859(3) 0.0490(10) Uani 1 1 d . . .
H3 H 0.6471 0.2537 0.5746 0.059 Uiso 1 1 calc R . .
N1 N 0.72079(16) 0.3323(4) 0.4886(3) 0.0500(9) Uani 1 1 d . . .
C5 C 0.79054(19) 0.3806(5) 0.5088(4) 0.0488(10) Uani 1 1 d . . .
H5 H 0.8076 0.4245 0.4460 0.059 Uiso 1 1 calc R . .
C6 C 0.83484(18) 0.3677(5) 0.6136(3) 0.0423(9) Uani 1 1 d . . .
C7 C 0.6769(2) 0.3374(5) 0.3733(4) 0.0501(10) Uani 1 1 d . . .
C8 C 0.6081(2) 0.3918(5) 0.3556(4) 0.0569(11) Uani 1 1 d . . .
H8 H 0.5894 0.4258 0.4193 0.068 Uiso 1 1 calc R . .
C9 C 0.5671(2) 0.3953(6) 0.2423(4) 0.0647(13) Uani 1 1 d . . .
H9 H 0.5204 0.4304 0.2299 0.078 Uiso 1 1 calc R . .
C10 C 0.5947(3) 0.3475(6) 0.1486(4) 0.0692(13) Uani 1 1 d . . .
H10 H 0.5668 0.3507 0.0726 0.083 Uiso 1 1 calc R . .
C11 C 0.6631(2) 0.2951(7) 0.1659(4) 0.0701(14) Uani 1 1 d . . .
H11 H 0.6817 0.2636 0.1017 0.084 Uiso 1 1 calc R . .
C12 C 0.7045(2) 0.2885(6) 0.2781(4) 0.0578(11) Uani 1 1 d . . .
H12 H 0.7509 0.2514 0.2898 0.069 Uiso 1 1 calc R . .
C13 C 0.84960(19) 0.1190(5) 0.7506(4) 0.0450(9) Uani 1 1 d . . .
C14 C 0.8852(2) 0.0823(6) 0.8631(4) 0.0570(11) Uani 1 1 d . . .
H14 H 0.8902 0.1638 0.9212 0.068 Uiso 1 1 calc R . .
C15 C 0.9139(2) -0.0740(7) 0.8921(5) 0.0711(14) Uani 1 1 d . . .
H15 H 0.9372 -0.0973 0.9692 0.085 Uiso 1 1 calc R . .
C16 C 0.9076(2) -0.1932(6) 0.8067(5) 0.0725(14) Uani 1 1 d . . .
H16 H 0.9276 -0.2973 0.8253 0.087 Uiso 1 1 calc R . .
C17 C 0.8716(3) -0.1600(6) 0.6927(5) 0.0666(12) Uani 1 1 d . . .
H17 H 0.8667 -0.2420 0.6350 0.080 Uiso 1 1 calc R . .
C18 C 0.8430(2) -0.0043(5) 0.6650(4) 0.0541(11) Uani 1 1 d . . .
H18 H 0.8191 0.0184 0.5881 0.065 Uiso 1 1 calc R . .
C19 C 0.9074(2) 0.4287(5) 0.6303(4) 0.0461(9) Uani 1 1 d . . .
C20 C 0.9927(2) 0.5630(6) 0.5429(4) 0.0672(13) Uani 1 1 d . . .
H20A H 0.9986 0.6543 0.5974 0.101 Uiso 1 1 calc R . .
H20B H 0.9990 0.6013 0.4673 0.101 Uiso 1 1 calc R . .
H20C H 1.0271 0.4789 0.5720 0.101 Uiso 1 1 calc R . .
C21 C 0.6041(2) 0.1104(7) 0.8547(4) 0.0751(14) Uani 1 1 d . . .
H21A H 0.6362 0.0446 0.9110 0.113 Uiso 1 1 calc R . .
H21B H 0.5627 0.0463 0.8228 0.113 Uiso 1 1 calc R . .
H21C H 0.5910 0.2075 0.8931 0.113 Uiso 1 1 calc R . .
C4 C 0.81451(19) 0.2879(5) 0.7201(3) 0.0431(9) Uani 1 1 d . . .
H4 H 0.8283 0.3620 0.7882 0.052 Uiso 1 1 calc R . .
O1 O 0.73331(14) 0.2324(4) 0.8965(3) 0.0668(9) Uani 1 1 d . . .
O2 O 0.63793(14) 0.1601(4) 0.7600(2) 0.0621(8) Uani 1 1 d . . .
O3 O 0.94950(14) 0.4254(4) 0.7237(3) 0.0594(8) Uani 1 1 d . . .
O4 O 0.92255(14) 0.4943(4) 0.5308(2) 0.0556(7) Uani 1 1 d . . .
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
O1 C1 O2 122.9(4) . . ?
O1 C1 C2 124.7(4) . . ?
O2 C1 C2 112.5(4) . . ?
C3 C2 C1 120.8(3) . . ?
C3 C2 C4 122.9(3) . . ?
C1 C2 C4 116.2(3) . . ?
C2 C3 N1 123.1(3) . . ?
C2 C3 H3 118.4 . . ?
N1 C3 H3 118.4 . . ?
C5 N1 C3 117.4(3) . . ?
C5 N1 C7 121.3(3) . . ?
C3 N1 C7 121.3(3) . . ?
C6 C5 N1 123.4(4) . . ?
C6 C5 H5 118.3 . . ?
N1 C5 H5 118.3 . . ?
C5 C6 C19 120.5(3) . . ?
C5 C6 C4 123.0(3) . . ?
C19 C6 C4 116.4(3) . . ?
C8 C7 C12 120.0(4) . . ?
C8 C7 N1 121.0(4) . . ?
C12 C7 N1 119.0(3) . . ?
C7 C8 C9 119.3(4) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C10 C9 C8 120.4(4) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 120.2(5) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C12 120.3(5) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C7 119.7(4) . . ?
C11 C12 H12 120.2 . . ?
C7 C12 H12 120.2 . . ?
C14 C13 C18 118.4(4) . . ?
C14 C13 C4 121.4(4) . . ?
C18 C13 C4 120.1(4) . . ?
C13 C14 C15 121.4(4) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C16 C15 C14 119.5(5) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C16 C17 120.4(5) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C18 C17 C16 119.6(5) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C13 120.8(4) . . ?
C17 C18 H18 119.6 . . ?
C13 C18 H18 119.6 . . ?
O3 C19 O4 122.9(4) . . ?
O3 C19 C6 123.8(4) . . ?
O4 C19 C6 113.3(3) . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O2 C21 H21A 109.5 . . ?
O2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C6 C4 C2 108.4(3) . . ?
C6 C4 C13 112.7(3) . . ?
C2 C4 C13 109.1(3) . . ?
C6 C4 H4 108.8 . . ?
C2 C4 H4 108.8 . . ?
C13 C4 H4 108.8 . . ?
C1 O2 C21 115.5(3) . . ?
C19 O4 C20 115.9(3) . . ?
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
C1 O1 1.207(5) . ?
C1 O2 1.343(5) . ?
C1 C2 1.466(5) . ?
C2 C3 1.328(5) . ?
C2 C4 1.524(5) . ?
C3 N1 1.396(5) . ?
C3 H3 0.9300 . ?
N1 C5 1.379(5) . ?
N1 C7 1.424(5) . ?
C5 C6 1.334(5) . ?
C5 H5 0.9300 . ?
C6 C19 1.465(5) . ?
C6 C4 1.516(5) . ?
C7 C8 1.379(6) . ?
C7 C12 1.382(5) . ?
C8 C9 1.383(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.365(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.366(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.376(6) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.371(5) . ?
C13 C18 1.391(5) . ?
C13 C4 1.528(5) . ?
C14 C15 1.388(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.366(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.382(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.381(6) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 O3 1.210(5) . ?
C19 O4 1.356(5) . ?
C20 O4 1.448(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 O2 1.451(5) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C4 H4 0.9800 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 3106436
