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#$Date: 2016-03-21 19:17:11 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178843 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/97/4109783.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_4109783
loop_
_publ_author_name
'Yuanyuan Wang'
'Jingxin Wang'
'Jiachun Su'
'Feng Huang'
'Lei Jiao'
'Yong Liang'
'Dazhi Yang'
'Shiwei Zhang'
'Paul A. Wender'
'Zhi-Xiang Yu'
_publ_contact_author_address
;
College of Chemistry
Peking University
202 Chengfu Road
Haidian District
Beijing, 100871
P.R. China
;
_publ_contact_author_email       yuzx@pku.edu.cn
_publ_contact_author_fax         '(86)10 6275 1708'
_publ_contact_author_name        'Zhi-Xiang Yu'
_publ_contact_author_phone       ' (86)10 6275 2612'
_publ_section_title
;
 A Computationally Designed Rh(I)-Catalyzed Two-Component [5+2+1]
 Cycloaddition of Ene-vinylcyclopropanes and CO for the Synthesis of
 Cyclooctenones
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10060
_journal_page_last               10061
_journal_paper_doi               10.1021/ja072505w
_journal_volume                  129
_journal_year                    2007
_chemical_compound_source        synthesis
_chemical_formula_moiety         'C17 H20 O2'
_chemical_formula_sum            'C17 H20 O2'
_chemical_formula_weight         256.33
_chemical_melting_point          361
_chemical_name_common            '5+2+1 product'
_chemical_name_systematic
cis-1-methyl-6-oxo-3-phenyl-10-oxabicyclo[6.3.0]undec-2-ene
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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                 98.86(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6264(17)
_cell_length_b                   11.231(2)
_cell_length_c                   14.416(3)
_cell_measurement_reflns_used    7408
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.02
_cell_measurement_theta_min      2.31
_cell_volume                     1380.0(5)
_computing_cell_refinement       Rapid-AUTO
_computing_data_collection       'Rapid-AUTO (Rigaku,2000)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC,2000)'
_computing_molecular_graphics    'Siemens SHELXTL V4.2,(Sheldrick,1990)'
_computing_publication_material  SHELXL-97,(Sheldrick,1997)
_computing_structure_refinement  SHELXL-97,(Sheldrick,1997)
_computing_structure_solution    SHELXS-97,(Sheldrick,1997)
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Rigaku RAXIS RAPID IP'
_diffrn_measurement_method       Ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0599
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7408
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.31
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
; 
                                  HIGASHI, T. (1995). Abscor-empirical
                                  Absorption Correction based on Fourier
                                  Series Approximation.
                                  Rigaku Corporation,Tokyo,Japan.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_recrystallization_method 'petroleum ether and EtOAc'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.041(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2390
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0427
_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)+(0.0400P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.0981
_reflns_number_gt                1303
_reflns_number_total             2390
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja072505wsi20070410_093741.cif
_cod_data_source_block           a
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4109783
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
O1 O 0.73994(17) 0.24555(13) 1.19807(10) 0.0697(5) Uani 1 1 d .
O2 O 0.20682(16) 0.11603(14) 0.97908(10) 0.0783(5) Uani 1 1 d .
C1 C 0.5693(2) 0.08398(16) 1.20907(12) 0.0426(5) Uani 1 1 d .
C2 C 0.5031(2) -0.02845(17) 1.16130(12) 0.0449(5) Uani 1 1 d .
H2 H 0.5709 -0.0710 1.1294 0.054 Uiso 1 1 calc R
C3 C 0.3610(2) -0.07463(17) 1.15872(12) 0.0430(5) Uani 1 1 d .
C4 C 0.2330(2) -0.00874(18) 1.19822(13) 0.0527(6) Uani 1 1 d .
H4A H 0.2791 0.0315 1.2554 0.063 Uiso 1 1 calc R
H4B H 0.1580 -0.0663 1.2148 0.063 Uiso 1 1 calc R
C5 C 0.1443(2) 0.08391(18) 1.13080(14) 0.0577(6) Uani 1 1 d .
H5A H 0.0516 0.0468 1.0961 0.069 Uiso 1 1 calc R
H5B H 0.1099 0.1485 1.1674 0.069 Uiso 1 1 calc R
C6 C 0.2416(2) 0.13425(19) 1.06261(15) 0.0548(6) Uani 1 1 d .
C7 C 0.3783(2) 0.21410(19) 1.09665(14) 0.0629(6) Uani 1 1 d .
H7A H 0.3402 0.2955 1.0916 0.075 Uiso 1 1 calc R
H7B H 0.4529 0.2060 1.0531 0.075 Uiso 1 1 calc R
C8 C 0.4688(2) 0.19824(16) 1.19551(13) 0.0487(5) Uani 1 1 d .
H8 H 0.3970 0.2017 1.2420 0.058 Uiso 1 1 calc R
C9 C 0.5953(2) 0.29425(18) 1.21600(16) 0.0692(7) Uani 1 1 d .
H9A H 0.5675 0.3630 1.1762 0.083 Uiso 1 1 calc R
H9B H 0.6047 0.3194 1.2810 0.083 Uiso 1 1 calc R
C10 C 0.7141(2) 0.12469(18) 1.16942(15) 0.0588(6) Uani 1 1 d .
H10A H 0.8040 0.0760 1.1939 0.071 Uiso 1 1 calc R
H10B H 0.6967 0.1188 1.1015 0.071 Uiso 1 1 calc R
C11 C 0.3242(2) -0.19372(17) 1.11607(12) 0.0447(5) Uani 1 1 d .
C12 C 0.4360(2) -0.28342(18) 1.12603(13) 0.0536(6) Uani 1 1 d .
H12 H 0.5339 -0.2691 1.1614 0.064 Uiso 1 1 calc R
C13 C 0.4053(3) -0.39354(18) 1.08463(14) 0.0632(6) Uani 1 1 d .
H13 H 0.4822 -0.4522 1.0919 0.076 Uiso 1 1 calc R
C14 C 0.2609(3) -0.4164(2) 1.03272(14) 0.0695(7) Uani 1 1 d .
H14 H 0.2401 -0.4902 1.0044 0.083 Uiso 1 1 calc R
C15 C 0.1485(3) -0.3299(2) 1.02309(14) 0.0684(7) Uani 1 1 d .
H15 H 0.0509 -0.3453 0.9879 0.082 Uiso 1 1 calc R
C16 C 0.1780(2) -0.21949(19) 1.06515(13) 0.0568(6) Uani 1 1 d .
H16 H 0.0991 -0.1622 1.0592 0.068 Uiso 1 1 calc R
C17 C 0.6148(2) 0.05717(18) 1.31426(12) 0.0601(6) Uani 1 1 d .
H17A H 0.5234 0.0327 1.3397 0.090 Uiso 1 1 calc R
H17B H 0.6580 0.1275 1.3462 0.090 Uiso 1 1 calc R
H17C H 0.6915 -0.0054 1.3226 0.090 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
C9 O1 C10 108.45(15)
C2 C1 C10 110.79(16)
C2 C1 C17 107.93(15)
C10 C1 C17 109.23(15)
C2 C1 C8 118.19(14)
C10 C1 C8 100.38(15)
C17 C1 C8 109.95(15)
C3 C2 C1 128.59(18)
C3 C2 H2 115.7
C1 C2 H2 115.7
C2 C3 C11 120.12(18)
C2 C3 C4 121.58(18)
C11 C3 C4 118.31(17)
C3 C4 C5 114.37(15)
C3 C4 H4A 108.7
C5 C4 H4A 108.7
C3 C4 H4B 108.7
C5 C4 H4B 108.7
H4A C4 H4B 107.6
C6 C5 C4 113.21(16)
C6 C5 H5A 108.9
C4 C5 H5A 108.9
C6 C5 H5B 108.9
C4 C5 H5B 108.9
H5A C5 H5B 107.7
O2 C6 C7 119.1(2)
O2 C6 C5 120.7(2)
C7 C6 C5 120.12(18)
C6 C7 C8 119.88(17)
C6 C7 H7A 107.4
C8 C7 H7A 107.4
C6 C7 H7B 107.4
C8 C7 H7B 107.4
H7A C7 H7B 106.9
C7 C8 C9 110.18(17)
C7 C8 C1 114.31(16)
C9 C8 C1 101.04(15)
C7 C8 H8 110.3
C9 C8 H8 110.3
C1 C8 H8 110.3
O1 C9 C8 108.27(17)
O1 C9 H9A 110.0
C8 C9 H9A 110.0
O1 C9 H9B 110.0
C8 C9 H9B 110.0
H9A C9 H9B 108.4
O1 C10 C1 106.12(16)
O1 C10 H10A 110.5
C1 C10 H10A 110.5
O1 C10 H10B 110.5
C1 C10 H10B 110.5
H10A C10 H10B 108.7
C12 C11 C16 117.65(18)
C12 C11 C3 120.64(17)
C16 C11 C3 121.71(18)
C13 C12 C11 121.41(19)
C13 C12 H12 119.3
C11 C12 H12 119.3
C14 C13 C12 120.0(2)
C14 C13 H13 120.0
C12 C13 H13 120.0
C15 C14 C13 119.5(2)
C15 C14 H14 120.2
C13 C14 H14 120.2
C14 C15 C16 120.9(2)
C14 C15 H15 119.6
C16 C15 H15 119.6
C15 C16 C11 120.5(2)
C15 C16 H16 119.7
C11 C16 H16 119.7
C1 C17 H17A 109.5
C1 C17 H17B 109.5
H17A C17 H17B 109.5
C1 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C9 1.422(2)
O1 C10 1.426(2)
O2 C6 1.213(2)
C1 C2 1.508(2)
C1 C10 1.522(3)
C1 C17 1.537(2)
C1 C8 1.544(2)
C2 C3 1.326(2)
C2 H2 0.9300
C3 C11 1.486(3)
C3 C4 1.512(2)
C4 C5 1.544(2)
C4 H4A 0.9700
C4 H4B 0.9700
C5 C6 1.498(3)
C5 H5A 0.9700
C5 H5B 0.9700
C6 C7 1.502(3)
C7 C8 1.527(2)
C7 H7A 0.9700
C7 H7B 0.9700
C8 C9 1.530(2)
C8 H8 0.9800
C9 H9A 0.9700
C9 H9B 0.9700
C10 H10A 0.9700
C10 H10B 0.9700
C11 C12 1.387(3)
C11 C16 1.389(3)
C12 C13 1.381(3)
C12 H12 0.9300
C13 C14 1.374(3)
C13 H13 0.9300
C14 C15 1.364(3)
C14 H14 0.9300
C15 C16 1.387(3)
C15 H15 0.9300
C16 H16 0.9300
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 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
C10 C1 C2 C3 -161.78(18)
C17 C1 C2 C3 78.7(2)
C8 C1 C2 C3 -46.8(3)
C1 C2 C3 C11 -173.44(16)
C1 C2 C3 C4 6.7(3)
C2 C3 C4 C5 82.9(2)
C11 C3 C4 C5 -96.9(2)
C3 C4 C5 C6 -27.8(2)
C4 C5 C6 O2 114.9(2)
C4 C5 C6 C7 -68.7(2)
O2 C6 C7 C8 -153.49(19)
C5 C6 C7 C8 30.1(3)
C6 C7 C8 C9 -176.48(19)
C6 C7 C8 C1 70.6(2)
C2 C1 C8 C7 -38.7(2)
C10 C1 C8 C7 81.77(18)
C17 C1 C8 C7 -163.23(16)
C2 C1 C8 C9 -157.03(17)
C10 C1 C8 C9 -36.52(18)
C17 C1 C8 C9 78.49(19)
C10 O1 C9 C8 -1.1(2)
C7 C8 C9 O1 -96.70(19)
C1 C8 C9 O1 24.5(2)
C9 O1 C10 C1 -23.7(2)
C2 C1 C10 O1 163.68(14)
C17 C1 C10 O1 -77.55(19)
C8 C1 C10 O1 37.99(18)
C2 C3 C11 C12 36.3(3)
C4 C3 C11 C12 -143.87(18)
C2 C3 C11 C16 -143.68(19)
C4 C3 C11 C16 36.1(3)
C16 C11 C12 C13 1.8(3)
C3 C11 C12 C13 -178.14(18)
C11 C12 C13 C14 -0.4(3)
C12 C13 C14 C15 -0.5(3)
C13 C14 C15 C16 -0.1(3)
C14 C15 C16 C11 1.6(3)
C12 C11 C16 C15 -2.4(3)
C3 C11 C16 C15 177.56(19)
