#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/35/4023549.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_4023549
loop_
_publ_author_name
'Min Shi'
'Xiang-Ying Tang'
'Yong-Hua Yang'
_publ_section_title
;
 Lewis Acid-Mediated Reactions of 1-Cyclopropyl-2-arylethanone
 Derivatives with Allenic Ester, Ethyl Acetoacetate,
 and Methyl Acrylate
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5311
_journal_page_last               5318
_journal_paper_doi               10.1021/jo800608h
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C19 H16 O3'
_chemical_formula_weight         292.32
_chemical_name_systematic
; 
 ? 
;
_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                 109.901(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9030(18)
_cell_length_b                   16.171(3)
_cell_length_c                   8.8944(15)
_cell_measurement_reflns_used    1496
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      47.605
_cell_measurement_theta_min      4.704
_cell_volume                     1474.6(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  '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  0.1517
_diffrn_reflns_av_sigmaI/netI    0.1177
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8607
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8183
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.428
_exptl_crystal_size_mid          0.327
_exptl_crystal_size_min          0.119
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0152(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.882
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3210
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.882
_refine_ls_R_factor_all          0.1004
_refine_ls_R_factor_gt           0.0605
_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)+(0.0407P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1397
_reflns_number_gt                1737
_reflns_number_total             3210
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo800608h-File003.cif
_cod_data_source_block           cd27586
_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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4023549
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
O1 O 1.10950(16) 1.17481(10) 0.81553(18) 0.0685(5) Uani 1 1 d . . .
O2 O 0.97025(13) 1.07202(9) 0.74181(14) 0.0493(4) Uani 1 1 d . . .
O3 O 0.66518(16) 0.86617(10) 0.64882(16) 0.0627(5) Uani 1 1 d . . .
C1 C 1.0329(2) 1.13876(14) 0.7036(3) 0.0500(6) Uani 1 1 d . . .
C2 C 0.9987(2) 1.15722(13) 0.5388(2) 0.0496(6) Uani 1 1 d . . .
H2 H 1.0435 1.1997 0.5096 0.060 Uiso 1 1 calc R . .
C3 C 0.9053(2) 1.11711(13) 0.4212(2) 0.0440(5) Uani 1 1 d . . .
C4 C 0.83193(18) 1.05114(12) 0.4634(2) 0.0393(5) Uani 1 1 d . . .
C5 C 0.87290(19) 1.03010(13) 0.6256(2) 0.0410(5) Uani 1 1 d . . .
C6 C 0.8157(2) 0.96806(13) 0.6845(2) 0.0431(5) Uani 1 1 d . . .
C7 C 0.7163(2) 0.92470(13) 0.5782(2) 0.0441(5) Uani 1 1 d . . .
C8 C 0.6679(2) 0.94099(13) 0.4149(2) 0.0415(5) Uani 1 1 d . . .
C9 C 0.7243(2) 1.00510(13) 0.3568(2) 0.0431(5) Uani 1 1 d . . .
C10 C 0.8340(2) 0.93858(15) 0.8507(2) 0.0602(7) Uani 1 1 d . . .
H10A H 0.8116 0.9813 0.9135 0.072 Uiso 1 1 calc R . .
H10B H 0.9229 0.9204 0.9055 0.072 Uiso 1 1 calc R . .
C11 C 0.7388(3) 0.86674(18) 0.8177(3) 0.0770(8) Uani 1 1 d . . .
H11A H 0.7858 0.8151 0.8488 0.092 Uiso 1 1 calc R . .
H11B H 0.6806 0.8732 0.8786 0.092 Uiso 1 1 calc R . .
C12 C 0.55814(19) 0.88882(12) 0.3108(2) 0.0409(5) Uani 1 1 d . . .
C13 C 0.4359(2) 0.89274(14) 0.3258(2) 0.0538(6) Uani 1 1 d . . .
H13 H 0.4213 0.9293 0.3986 0.065 Uiso 1 1 calc R . .
C14 C 0.3361(2) 0.84328(15) 0.2344(3) 0.0589(6) Uani 1 1 d . . .
H14 H 0.2547 0.8466 0.2462 0.071 Uiso 1 1 calc R . .
C15 C 0.3548(2) 0.78968(14) 0.1273(2) 0.0570(6) Uani 1 1 d . . .
H15 H 0.2867 0.7563 0.0660 0.068 Uiso 1 1 calc R . .
C16 C 0.4749(2) 0.78495(15) 0.1096(3) 0.0649(7) Uani 1 1 d . . .
H16 H 0.4882 0.7484 0.0359 0.078 Uiso 1 1 calc R . .
C17 C 0.5758(2) 0.83440(15) 0.2011(2) 0.0585(6) Uani 1 1 d . . .
H17 H 0.6569 0.8309 0.1885 0.070 Uiso 1 1 calc R . .
C18 C 0.8857(2) 1.14375(15) 0.2527(2) 0.0636(7) Uani 1 1 d . . .
H18A H 0.8035 1.1717 0.2093 0.095 Uiso 1 1 calc R . .
H18B H 0.8863 1.0960 0.1888 0.095 Uiso 1 1 calc R . .
H18C H 0.9548 1.1805 0.2526 0.095 Uiso 1 1 calc R . .
C19 C 0.6623(3) 1.02757(17) 0.1825(2) 0.0718(8) Uani 1 1 d . . .
H19A H 0.7178 1.0098 0.1249 0.108 Uiso 1 1 calc R . .
H19B H 0.6507 1.0864 0.1724 0.108 Uiso 1 1 calc R . .
H19C H 0.5791 1.0008 0.1394 0.108 Uiso 1 1 calc R . .
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'
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
C1 O2 C5 121.20(16) . . ?
C7 O3 C11 107.88(16) . . ?
O1 C1 O2 115.8(2) . . ?
O1 C1 C2 128.0(2) . . ?
O2 C1 C2 116.24(18) . . ?
C3 C2 C1 124.3(2) . . ?
C3 C2 H2 117.9 . . ?
C1 C2 H2 117.9 . . ?
C2 C3 C4 119.14(18) . . ?
C2 C3 C18 116.6(2) . . ?
C4 C3 C18 124.23(18) . . ?
C5 C4 C9 117.12(19) . . ?
C5 C4 C3 115.66(17) . . ?
C9 C4 C3 127.21(17) . . ?
C6 C5 O2 113.91(17) . . ?
C6 C5 C4 122.90(18) . . ?
O2 C5 C4 123.14(19) . . ?
C7 C6 C5 117.82(18) . . ?
C7 C6 C10 109.1(2) . . ?
C5 C6 C10 132.96(18) . . ?
O3 C7 C6 113.10(17) . . ?
O3 C7 C8 123.09(18) . . ?
C6 C7 C8 123.7(2) . . ?
C9 C8 C7 118.04(18) . . ?
C9 C8 C12 123.44(17) . . ?
C7 C8 C12 118.52(19) . . ?
C8 C9 C4 120.33(17) . . ?
C8 C9 C19 117.43(18) . . ?
C4 C9 C19 122.10(19) . . ?
C6 C10 C11 101.52(16) . . ?
C6 C10 H10A 111.5 . . ?
C11 C10 H10A 111.5 . . ?
C6 C10 H10B 111.5 . . ?
C11 C10 H10B 111.5 . . ?
H10A C10 H10B 109.3 . . ?
O3 C11 C10 107.92(17) . . ?
O3 C11 H11A 110.1 . . ?
C10 C11 H11A 110.1 . . ?
O3 C11 H11B 110.1 . . ?
C10 C11 H11B 110.1 . . ?
H11A C11 H11B 108.4 . . ?
C17 C12 C13 117.98(19) . . ?
C17 C12 C8 121.55(19) . . ?
C13 C12 C8 120.45(18) . . ?
C14 C13 C12 120.8(2) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C15 C14 C13 120.7(2) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 119.6(2) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C15 C16 C17 120.0(2) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C12 C17 C16 120.9(2) . . ?
C12 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C3 C18 H18A 109.5 . . ?
C3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C9 C19 H19A 109.5 . . ?
C9 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C9 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
O1 C1 1.209(2) . ?
O2 C1 1.380(3) . ?
O2 C5 1.381(2) . ?
O3 C7 1.356(2) . ?
O3 C11 1.442(2) . ?
C1 C2 1.416(3) . ?
C2 C3 1.352(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.457(3) . ?
C3 C18 1.503(3) . ?
C4 C5 1.399(2) . ?
C4 C9 1.440(3) . ?
C5 C6 1.376(3) . ?
C6 C7 1.365(3) . ?
C6 C10 1.500(3) . ?
C7 C8 1.392(2) . ?
C8 C9 1.391(3) . ?
C8 C12 1.499(3) . ?
C9 C19 1.509(3) . ?
C10 C11 1.518(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C17 1.375(3) . ?
C12 C13 1.385(3) . ?
C13 C14 1.372(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.354(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.373(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.379(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 O2 C1 O1 174.62(18) . . . . ?
C5 O2 C1 C2 -4.7(3) . . . . ?
O1 C1 C2 C3 -175.3(2) . . . . ?
O2 C1 C2 C3 3.9(3) . . . . ?
C1 C2 C3 C4 1.0(3) . . . . ?
C1 C2 C3 C18 -178.18(19) . . . . ?
C2 C3 C4 C5 -5.0(3) . . . . ?
C18 C3 C4 C5 174.09(19) . . . . ?
C2 C3 C4 C9 175.91(19) . . . . ?
C18 C3 C4 C9 -5.0(3) . . . . ?
C1 O2 C5 C6 -176.66(19) . . . . ?
C1 O2 C5 C4 0.6(3) . . . . ?
C9 C4 C5 C6 0.5(3) . . . . ?
C3 C4 C5 C6 -178.65(19) . . . . ?
C9 C4 C5 O2 -176.49(17) . . . . ?
C3 C4 C5 O2 4.4(3) . . . . ?
O2 C5 C6 C7 178.46(17) . . . . ?
C4 C5 C6 C7 1.2(3) . . . . ?
O2 C5 C6 C10 2.8(3) . . . . ?
C4 C5 C6 C10 -174.5(2) . . . . ?
C11 O3 C7 C6 -2.5(3) . . . . ?
C11 O3 C7 C8 -179.7(2) . . . . ?
C5 C6 C7 O3 -178.82(18) . . . . ?
C10 C6 C7 O3 -2.2(3) . . . . ?
C5 C6 C7 C8 -1.5(3) . . . . ?
C10 C6 C7 C8 175.12(19) . . . . ?
O3 C7 C8 C9 177.08(19) . . . . ?
C6 C7 C8 C9 0.1(3) . . . . ?
O3 C7 C8 C12 -2.9(3) . . . . ?
C6 C7 C8 C12 -179.9(2) . . . . ?
C7 C8 C9 C4 1.7(3) . . . . ?
C12 C8 C9 C4 -178.26(18) . . . . ?
C7 C8 C9 C19 -174.10(19) . . . . ?
C12 C8 C9 C19 5.9(3) . . . . ?
C5 C4 C9 C8 -2.0(3) . . . . ?
C3 C4 C9 C8 177.0(2) . . . . ?
C5 C4 C9 C19 173.6(2) . . . . ?
C3 C4 C9 C19 -7.3(3) . . . . ?
C7 C6 C10 C11 5.4(3) . . . . ?
C5 C6 C10 C11 -178.6(2) . . . . ?
C7 O3 C11 C10 6.0(3) . . . . ?
C6 C10 C11 O3 -6.8(3) . . . . ?
C9 C8 C12 C17 68.5(3) . . . . ?
C7 C8 C12 C17 -111.5(2) . . . . ?
C9 C8 C12 C13 -113.2(2) . . . . ?
C7 C8 C12 C13 66.8(3) . . . . ?
C17 C12 C13 C14 0.4(3) . . . . ?
C8 C12 C13 C14 -178.0(2) . . . . ?
C12 C13 C14 C15 -0.2(3) . . . . ?
C13 C14 C15 C16 -0.2(4) . . . . ?
C14 C15 C16 C17 0.2(4) . . . . ?
C13 C12 C17 C16 -0.4(3) . . . . ?
C8 C12 C17 C16 178.0(2) . . . . ?
C15 C16 C17 C12 0.0(4) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658702
