#------------------------------------------------------------------------------
#$Date: 2017-10-14 21:27:35 +0200 (Sat 14 de Oct de 2017) $
#$Revision: 202017 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/19/7151934.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_7151934
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         'C19 H13 N3'
_chemical_formula_sum            'C19 H13 N3'
_chemical_formula_weight         283.32
_chemical_name_systematic
;
?
;
_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                90.00
_cell_angle_beta                 94.69(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.657(3)
_cell_length_b                   8.1149(16)
_cell_length_c                   13.751(3)
_cell_measurement_reflns_used    2895
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.89
_cell_measurement_theta_min      2.35
_cell_volume                     1518.9(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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0444
_diffrn_reflns_av_sigmaI/netI    0.0384
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9938
_diffrn_reflns_theta_full        25.20
_diffrn_reflns_theta_max         25.20
_diffrn_reflns_theta_min         3.22
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Jacobson, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.114
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2728
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0429
_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)+(0.0576P)²+0.1912P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1039
_refine_ls_wR_factor_ref         0.1265
_reflns_number_gt                1848
_reflns_number_total             2728
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ob05440f.txt
_cod_data_source_block           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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1518.8(5)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7151934
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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.24493(12) 0.0335(2) 0.72009(11) 0.0618(4) Uani 1 1 d . . .
C2 C 0.29859(12) -0.0037(2) 0.80702(12) 0.0647(4) Uani 1 1 d . . .
H2 H 0.2667 -0.0350 0.8613 0.078 Uiso 1 1 calc R . .
C3 C 0.39921(13) 0.0060(2) 0.81246(12) 0.0703(5) Uani 1 1 d . . .
H3 H 0.4354 -0.0175 0.8711 0.084 Uiso 1 1 calc R . .
C4 C 0.44707(14) 0.0499(2) 0.73227(13) 0.0741(5) Uani 1 1 d . . .
H4 H 0.5153 0.0550 0.7363 0.089 Uiso 1 1 calc R . .
C5 C 0.39331(14) 0.0863(3) 0.64619(13) 0.0812(5) Uani 1 1 d . . .
H5 H 0.4255 0.1159 0.5918 0.097 Uiso 1 1 calc R . .
C6 C 0.29235(14) 0.0793(2) 0.63965(12) 0.0769(5) Uani 1 1 d . . .
H6 H 0.2564 0.1054 0.5813 0.092 Uiso 1 1 calc R . .
N1 N 0.13993(10) 0.02448(18) 0.71470(10) 0.0680(4) Uani 1 1 d . . .
C7 C 0.08783(13) -0.0660(2) 0.64304(11) 0.0653(4) Uani 1 1 d . . .
H7 H 0.1216 -0.1118 0.5936 0.078 Uiso 1 1 calc R . .
C8 C -0.00864(12) -0.09083(19) 0.64149(11) 0.0609(4) Uani 1 1 d . . .
C10 C -0.00821(13) 0.0707(2) 0.79147(11) 0.0651(4) Uani 1 1 d . . .
C11 C 0.08850(13) 0.0889(2) 0.78800(12) 0.0685(5) Uani 1 1 d . . .
H11 H 0.1230 0.1480 0.8376 0.082 Uiso 1 1 calc R . .
C12 C -0.05553(13) -0.1946(2) 0.56776(12) 0.0702(5) Uani 1 1 d . . .
C13 C -0.05317(14) 0.1419(3) 0.87142(13) 0.0803(5) Uani 1 1 d . . .
C14 C -0.15448(11) 0.0861(2) 0.66542(11) 0.0603(4) Uani 1 1 d . . .
C15 C -0.13454(14) 0.2414(2) 0.63207(13) 0.0778(5) Uani 1 1 d . . .
H15 H -0.0713 0.2837 0.6424 0.093 Uiso 1 1 calc R . .
C16 C -0.20774(19) 0.3357(3) 0.58324(15) 0.0972(7) Uani 1 1 d . . .
H16 H -0.1938 0.4411 0.5617 0.117 Uiso 1 1 calc R . .
C17 C -0.30081(18) 0.2726(4) 0.56692(16) 0.1023(8) Uani 1 1 d . . .
H17 H -0.3502 0.3355 0.5345 0.123 Uiso 1 1 calc R . .
C18 C -0.32076(16) 0.1184(4) 0.59811(17) 0.1040(8) Uani 1 1 d . . .
H18 H -0.3836 0.0751 0.5856 0.125 Uiso 1 1 calc R . .
C19 C -0.24881(14) 0.0258(3) 0.64805(14) 0.0845(6) Uani 1 1 d . . .
H19 H -0.2639 -0.0786 0.6704 0.101 Uiso 1 1 calc R . .
C9 C -0.07407(12) -0.0210(2) 0.71515(11) 0.0622(4) Uani 1 1 d . . .
H9 H -0.1050 -0.1130 0.7472 0.075 Uiso 1 1 calc R . .
N2 N -0.09657(13) -0.2785(2) 0.51187(12) 0.0937(5) Uani 1 1 d . . .
N3 N -0.09056(15) 0.1961(3) 0.93547(14) 0.1182(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'
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
C6 C1 C2 120.13(16) . . ?
C6 C1 N1 120.45(15) . . ?
C2 C1 N1 119.42(15) . . ?
C3 C2 C1 119.47(16) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C4 C3 C2 120.73(16) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 119.45(17) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 120.67(17) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C1 C6 C5 119.54(16) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C11 N1 C7 117.42(14) . . ?
C11 N1 C1 120.74(13) . . ?
C7 N1 C1 121.35(13) . . ?
C8 C7 N1 122.97(15) . . ?
C8 C7 H7 118.5 . . ?
N1 C7 H7 118.5 . . ?
C7 C8 C12 119.09(15) . . ?
C7 C8 C9 124.75(14) . . ?
C12 C8 C9 116.12(15) . . ?
C11 C10 C13 118.26(15) . . ?
C11 C10 C9 124.14(15) . . ?
C13 C10 C9 117.60(15) . . ?
C10 C11 N1 123.37(15) . . ?
C10 C11 H11 118.3 . . ?
N1 C11 H11 118.3 . . ?
N2 C12 C8 176.6(2) . . ?
N3 C13 C10 178.5(2) . . ?
C15 C14 C19 118.31(17) . . ?
C15 C14 C9 121.24(15) . . ?
C19 C14 C9 120.37(16) . . ?
C14 C15 C16 120.79(19) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 119.6(2) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C18 C17 C16 120.0(2) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.5(2) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C18 C19 C14 120.8(2) . . ?
C18 C19 H19 119.6 . . ?
C14 C19 H19 119.6 . . ?
C8 C9 C14 110.95(12) . . ?
C8 C9 C10 107.27(13) . . ?
C14 C9 C10 113.32(13) . . ?
C8 C9 H9 108.4 . . ?
C14 C9 H9 108.4 . . ?
C10 C9 H9 108.4 . . ?
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 C6 1.378(2) . ?
C1 C2 1.383(2) . ?
C1 N1 1.432(2) . ?
C2 C3 1.372(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.376(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N1 C11 1.378(2) . ?
N1 C7 1.379(2) . ?
C7 C8 1.331(2) . ?
C7 H7 0.9300 . ?
C8 C12 1.428(2) . ?
C8 C9 1.514(2) . ?
C10 C11 1.334(2) . ?
C10 C13 1.424(2) . ?
C10 C9 1.520(2) . ?
C11 H11 0.9300 . ?
C12 N2 1.139(2) . ?
C13 N3 1.142(2) . ?
C14 C15 1.376(2) . ?
C14 C19 1.380(2) . ?
C14 C9 1.519(2) . ?
C15 C16 1.388(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.372(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.358(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.375(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C9 H9 0.9800 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653512
