#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:27:38 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178783 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/37/4103788.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_4103788
loop_
_publ_author_name
'Zengming Shen'
'Peter K. Dornan'
'Hasan A. Khan'
'Tom K. Woo'
'Vy M. Dong'
_publ_section_title
;
 Mechanistic Insights into the Rhodium-Catalyzed Intramolecular Ketone
 Hydroacylation
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1077
_journal_page_last               1091
_journal_paper_doi               10.1021/ja806758m
_journal_volume                  131
_journal_year                    2009
_chemical_formula_moiety         'C21 H16 O3'
_chemical_formula_sum            'C21 H16 O3'
_chemical_formula_weight         316.34
_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                 115.066(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.0252(3)
_cell_length_b                   18.0030(11)
_cell_length_c                   9.7974(5)
_cell_measurement_reflns_used    9824
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      25.1
_cell_measurement_theta_min      2.6
_cell_volume                     1601.74(14)
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius B.V., 1997-2002)'
_computing_data_reduction        Denzo-SMN
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXTL V6.1'
_computing_structure_refinement  'SHELXTL V6.1 (Sheldrick, 2008)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_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  0.0676
_diffrn_reflns_av_sigmaI/netI    0.0579
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9824
_diffrn_reflns_theta_full        25.07
_diffrn_reflns_theta_max         25.07
_diffrn_reflns_theta_min         2.56
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.004
_exptl_absorpt_correction_T_min  0.685
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
 Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2833
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0460
_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)+(0.0632P)²+0.0124P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1221
_reflns_number_gt                1963
_reflns_number_total             2833
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ja806758m_si_002.cif
_cod_data_source_block           k08120a
_cod_original_cell_volume        1601.73(14)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4103788
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
O1 O 1.04289(13) 0.24382(7) 0.64138(12) 0.0335(3) Uani 1 1 d .
O2 O 1.09435(12) 0.13131(7) 0.85339(12) 0.0306(3) Uani 1 1 d .
O3 O 1.33656(15) 0.12308(8) 0.95404(16) 0.0459(4) Uani 1 1 d .
C1 C 1.14204(19) 0.28318(10) 0.76409(18) 0.0294(5) Uani 1 1 d .
C2 C 1.1520(2) 0.35940(11) 0.75383(19) 0.0337(5) Uani 1 1 d .
H2A H 1.0878 0.3849 0.6655 0.040 Uiso 1 1 calc R
C3 C 1.2565(2) 0.39831(11) 0.8736(2) 0.0384(5) Uani 1 1 d .
H3A H 1.2633 0.4507 0.8676 0.046 Uiso 1 1 calc R
C4 C 1.3512(2) 0.36108(11) 1.0021(2) 0.0385(5) Uani 1 1 d .
H4A H 1.4217 0.3881 1.0843 0.046 Uiso 1 1 calc R
C5 C 1.3433(2) 0.28460(11) 1.0108(2) 0.0355(5) Uani 1 1 d .
H5A H 1.4098 0.2591 1.0980 0.043 Uiso 1 1 calc R
C6 C 1.23810(18) 0.24498(10) 0.89218(18) 0.0297(4) Uani 1 1 d .
C7 C 1.2299(2) 0.16296(11) 0.90273(19) 0.0320(5) Uani 1 1 d .
C8 C 0.96883(18) 0.17992(10) 0.81732(18) 0.0269(4) Uani 1 1 d .
H8A H 1.0015 0.2232 0.8880 0.032 Uiso 1 1 calc R
C9 C 0.91936(19) 0.20980(10) 0.65702(18) 0.0294(4) Uani 1 1 d .
H9A H 0.8424 0.2486 0.6391 0.035 Uiso 1 1 calc R
C10 C 0.8568(2) 0.15135(11) 0.53502(19) 0.0318(5) Uani 1 1 d .
C11 C 0.7075(2) 0.13501(11) 0.4758(2) 0.0399(5) Uani 1 1 d .
H11A H 0.6461 0.1610 0.5115 0.048 Uiso 1 1 calc R
C12 C 0.6467(2) 0.08127(13) 0.3650(2) 0.0470(6) Uani 1 1 d .
H12A H 0.5446 0.0703 0.3260 0.056 Uiso 1 1 calc R
C13 C 0.7350(2) 0.04375(12) 0.3114(2) 0.0489(6) Uani 1 1 d .
H13A H 0.6939 0.0068 0.2357 0.059 Uiso 1 1 calc R
C14 C 0.8825(2) 0.06016(12) 0.3684(2) 0.0485(6) Uani 1 1 d .
H14A H 0.9430 0.0347 0.3309 0.058 Uiso 1 1 calc R
C15 C 0.9446(2) 0.11361(11) 0.4804(2) 0.0407(5) Uani 1 1 d .
H15A H 1.0469 0.1242 0.5193 0.049 Uiso 1 1 calc R
C16 C 0.85085(18) 0.13963(10) 0.84436(17) 0.0266(4) Uani 1 1 d .
C17 C 0.8563(2) 0.06391(11) 0.87144(18) 0.0324(5) Uani 1 1 d .
H17A H 0.9335 0.0348 0.8670 0.039 Uiso 1 1 calc R
C18 C 0.7488(2) 0.03047(12) 0.9050(2) 0.0382(5) Uani 1 1 d .
H18A H 0.7530 -0.0214 0.9238 0.046 Uiso 1 1 calc R
C19 C 0.6363(2) 0.07198(12) 0.91136(19) 0.0380(5) Uani 1 1 d .
H19A H 0.5638 0.0489 0.9355 0.046 Uiso 1 1 calc R
C20 C 0.6290(2) 0.14738(12) 0.88248(19) 0.0358(5) Uani 1 1 d .
H20A H 0.5510 0.1761 0.8858 0.043 Uiso 1 1 calc R
C21 C 0.7358(2) 0.18098(11) 0.84861(19) 0.0320(5) Uani 1 1 d .
H21A H 0.7301 0.2328 0.8281 0.038 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
C1 O1 C9 117.12(12)
C7 O2 C8 117.89(14)
C2 C1 O1 119.43(15)
C2 C1 C6 120.70(16)
O1 C1 C6 119.70(16)
C1 C2 C3 119.45(17)
C4 C3 C2 120.34(19)
C5 C4 C3 120.11(17)
C4 C5 C6 120.14(17)
C5 C6 C1 119.23(17)
C5 C6 C7 119.79(16)
C1 C6 C7 120.98(16)
O3 C7 O2 118.33(17)
O3 C7 C6 123.73(17)
O2 C7 C6 117.94(16)
O2 C8 C16 109.42(14)
O2 C8 C9 109.46(13)
C16 C8 C9 114.41(14)
O1 C9 C10 107.29(13)
O1 C9 C8 109.74(13)
C10 C9 C8 114.30(15)
C15 C10 C11 118.89(17)
C15 C10 C9 121.80(17)
C11 C10 C9 119.31(16)
C12 C11 C10 120.85(19)
C13 C12 C11 119.92(19)
C14 C13 C12 119.55(19)
C13 C14 C15 120.9(2)
C10 C15 C14 119.88(19)
C17 C16 C21 119.18(16)
C17 C16 C8 122.57(16)
C21 C16 C8 118.18(16)
C16 C17 C18 119.98(17)
C19 C18 C17 120.52(19)
C18 C19 C20 119.84(17)
C19 C20 C21 119.87(18)
C20 C21 C16 120.59(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.387(2)
O1 C9 1.447(2)
O2 C7 1.360(2)
O2 C8 1.448(2)
O3 C7 1.207(2)
C1 C2 1.383(3)
C1 C6 1.397(2)
C2 C3 1.387(3)
C3 C4 1.386(3)
C4 C5 1.384(3)
C5 C6 1.390(2)
C6 C7 1.485(3)
C8 C16 1.503(2)
C8 C9 1.530(2)
C9 C10 1.515(2)
C10 C15 1.386(3)
C10 C11 1.389(3)
C11 C12 1.388(3)
C12 C13 1.381(3)
C13 C14 1.374(3)
C14 C15 1.393(3)
C16 C17 1.385(3)
C16 C21 1.388(2)
C17 C18 1.391(2)
C18 C19 1.376(3)
C19 C20 1.382(3)
C20 C21 1.387(2)
