#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/16/7151680.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_7151680
loop_
_publ_author_name
'Wang, De-Wei'
'Syu, Siang-en'
'Hung, Yi-Ting'
'Chen, Pei-yi'
'Lee, Chia-Jui'
'Chen, Ko-Wei'
'Chen, Yu-Jhang'
'Lin, Wenwei'
_publ_section_title
;
 Organocatalytic tandem three-component reaction of aldehyde, alkyl
 vinyl ketone, and amide: one-pot syntheses of highly functional
 alkenes.
;
_journal_issue                   2
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              363
_journal_page_last               366
_journal_paper_doi               10.1039/C0OB00644K
_journal_volume                  9
_journal_year                    2011
_chemical_formula_moiety         'C19 H16 Cl N O4'
_chemical_formula_sum            'C19 H16 Cl N O4'
_chemical_formula_weight         357.78
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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                 101.014(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.8329(3)
_cell_length_b                   16.6085(6)
_cell_length_c                   13.2043(5)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     1686.14(11)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_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  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10425
_diffrn_reflns_theta_full        24.96
_diffrn_reflns_theta_max         24.96
_diffrn_reflns_theta_min         2.45
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_T_max  0.9241
_exptl_absorpt_correction_T_min  0.8683
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.138
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.164
_refine_ls_hydrogen_treatment    fixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2918
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.164
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0411
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0790P)²+0.4627P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1190
_refine_ls_wR_factor_ref         0.1432
_reflns_number_gt                2423
_reflns_number_total             2918
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0OB00644K.TXT
_cod_data_source_block           a10539
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7151680
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
C1 C 0.4601(3) 0.67404(14) -0.05993(16) 0.0367(6) Uani 1 1 d . . .
C2 C 0.5027(4) 0.59361(15) -0.06934(17) 0.0455(6) Uani 1 1 d . . .
H2 H 0.4145 0.5536 -0.0775 0.055 Uiso 1 1 calc R . .
C3 C 0.6731(4) 0.57220(15) -0.06672(18) 0.0483(7) Uani 1 1 d . . .
H3 H 0.7034 0.5171 -0.0716 0.058 Uiso 1 1 calc R . .
C4 C 0.7998(4) 0.63078(14) -0.05697(17) 0.0415(6) Uani 1 1 d . . .
H4 H 0.9172 0.6163 -0.0569 0.050 Uiso 1 1 calc R . .
C5 C 0.7556(3) 0.71124(13) -0.04723(16) 0.0324(5) Uani 1 1 d . . .
H5 H 0.8440 0.7511 -0.0410 0.039 Uiso 1 1 calc R . .
C6 C 0.5862(3) 0.73466(12) -0.04643(14) 0.0276(5) Uani 1 1 d . . .
C7 C 0.5388(3) 0.82211(12) -0.03225(15) 0.0279(5) Uani 1 1 d . . .
H7 H 0.4384 0.8366 -0.0881 0.033 Uiso 1 1 calc R . .
C8 C 0.4850(3) 0.83754(12) 0.07425(15) 0.0287(5) Uani 1 1 d . . .
H8 H 0.4033 0.7939 0.0865 0.034 Uiso 1 1 calc R . .
C9 C 0.3897(3) 0.91772(13) 0.06886(15) 0.0325(5) Uani 1 1 d . . .
C10 C 0.2057(3) 0.92032(16) 0.01128(19) 0.0458(6) Uani 1 1 d . . .
H10A H 0.1601 0.9751 0.0134 0.069 Uiso 1 1 calc R . .
H10B H 0.1347 0.8831 0.0433 0.069 Uiso 1 1 calc R . .
H10C H 0.2018 0.9045 -0.0606 0.069 Uiso 1 1 calc R . .
C11 C 0.6381(3) 0.83986(13) 0.16611(16) 0.0348(5) Uani 1 1 d . . .
H11A H 0.7187 0.8833 0.1545 0.042 Uiso 1 1 calc R . .
H11B H 0.5931 0.8535 0.2291 0.042 Uiso 1 1 calc R . .
C12 C 0.6657(3) 0.69083(12) 0.20550(14) 0.0259(5) Uani 1 1 d . . .
C13 C 0.8115(3) 0.63232(12) 0.21877(14) 0.0247(5) Uani 1 1 d . . .
C14 C 0.8145(3) 0.55049(13) 0.23753(16) 0.0346(5) Uani 1 1 d . . .
H14 H 0.7121 0.5223 0.2450 0.042 Uiso 1 1 calc R . .
C15 C 0.9721(3) 0.51106(14) 0.24508(18) 0.0437(6) Uani 1 1 d . . .
H15 H 0.9781 0.4547 0.2577 0.052 Uiso 1 1 calc R . .
C16 C 1.1220(3) 0.55275(16) 0.23451(18) 0.0446(6) Uani 1 1 d . . .
H16 H 1.2288 0.5243 0.2409 0.054 Uiso 1 1 calc R . .
C17 C 1.1188(3) 0.63455(14) 0.21496(17) 0.0368(5) Uani 1 1 d . . .
H17 H 1.2208 0.6629 0.2070 0.044 Uiso 1 1 calc R . .
C18 C 0.9606(3) 0.67331(12) 0.20745(15) 0.0263(5) Uani 1 1 d . . .
C19 C 0.9140(3) 0.75906(13) 0.18597(15) 0.0293(5) Uani 1 1 d . . .
Cl1 Cl 0.24102(8) 0.69825(5) -0.06709(6) 0.0591(3) Uani 1 1 d . . .
N1 N 0.7354(2) 0.76443(10) 0.18376(12) 0.0262(4) Uani 1 1 d . . .
O1 O 0.6825(2) 0.87097(9) -0.04328(12) 0.0363(4) Uani 1 1 d . . .
H1 H 0.6576 0.9196 -0.0361 0.054 Uiso 1 1 calc R . .
O2 O 0.4614(2) 0.97735(9) 0.11115(13) 0.0435(4) Uani 1 1 d . . .
O3 O 0.51493(19) 0.67990(10) 0.21124(12) 0.0410(4) Uani 1 1 d . . .
O4 O 1.0071(2) 0.81461(9) 0.17248(13) 0.0454(5) 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'
Cl Cl 0.1484 0.1585 '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 C1 C6 121.9(2) . . ?
C2 C1 Cl1 117.82(19) . . ?
C6 C1 Cl1 120.24(18) . . ?
C3 C2 C1 119.7(2) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 119.9(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 119.9(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 121.7(2) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C1 116.8(2) . . ?
C5 C6 C7 121.73(19) . . ?
C1 C6 C7 121.4(2) . . ?
O1 C7 C6 108.52(16) . . ?
O1 C7 C8 110.74(16) . . ?
C6 C7 C8 112.42(16) . . ?
O1 C7 H7 108.4 . . ?
C6 C7 H7 108.4 . . ?
C8 C7 H7 108.4 . . ?
C9 C8 C11 108.50(17) . . ?
C9 C8 C7 108.38(16) . . ?
C11 C8 C7 114.25(18) . . ?
C9 C8 H8 108.5 . . ?
C11 C8 H8 108.5 . . ?
C7 C8 H8 108.5 . . ?
O2 C9 C10 121.6(2) . . ?
O2 C9 C8 120.68(19) . . ?
C10 C9 C8 117.7(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 . . ?
N1 C11 C8 114.16(17) . . ?
N1 C11 H11A 108.7 . . ?
C8 C11 H11A 108.7 . . ?
N1 C11 H11B 108.7 . . ?
C8 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
O3 C12 N1 124.77(19) . . ?
O3 C12 C13 129.20(19) . . ?
N1 C12 C13 106.03(16) . . ?
C14 C13 C18 121.2(2) . . ?
C14 C13 C12 130.6(2) . . ?
C18 C13 C12 108.14(17) . . ?
C13 C14 C15 117.6(2) . . ?
C13 C14 H14 121.2 . . ?
C15 C14 H14 121.2 . . ?
C14 C15 C16 121.0(2) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C17 C16 C15 121.4(2) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C18 C17 C16 117.1(2) . . ?
C18 C17 H17 121.5 . . ?
C16 C17 H17 121.5 . . ?
C17 C18 C13 121.7(2) . . ?
C17 C18 C19 130.1(2) . . ?
C13 C18 C19 108.13(17) . . ?
O4 C19 N1 125.27(19) . . ?
O4 C19 C18 128.8(2) . . ?
N1 C19 C18 105.90(17) . . ?
C12 N1 C19 111.75(16) . . ?
C12 N1 C11 124.96(17) . . ?
C19 N1 C11 123.21(18) . . ?
C7 O1 H1 109.5 . . ?
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
C1 C2 1.388(3) . ?
C1 C6 1.397(3) . ?
C1 Cl1 1.748(3) . ?
C2 C3 1.376(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.378(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.519(3) . ?
C7 O1 1.417(3) . ?
C7 C8 1.564(3) . ?
C7 H7 1.0000 . ?
C8 C9 1.522(3) . ?
C8 C11 1.534(3) . ?
C8 H8 1.0000 . ?
C9 O2 1.220(3) . ?
C9 C10 1.496(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 N1 1.462(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 O3 1.211(2) . ?
C12 N1 1.391(3) . ?
C12 C13 1.485(3) . ?
C13 C14 1.381(3) . ?
C13 C18 1.384(3) . ?
C14 C15 1.384(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.393(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.382(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.383(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.484(3) . ?
C19 O4 1.210(3) . ?
C19 N1 1.397(3) . ?
O1 H1 0.8400 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139190575
