#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:55:56 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180323 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/37/7153704.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_7153704
loop_
_publ_author_name
'Zhu, Shifa'
'Hu, Lang'
'Jiang, Huanfeng'
_publ_section_title
;
 Gold-catalyzed tandem Diels-Alder reactions of enynals/enynones with
 alkenes: generation and trapping of cyclic o-QDMs.
;
_journal_issue                   24
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4104
_journal_page_last               4111
_journal_paper_doi               10.1039/c4ob00321g
_journal_volume                  12
_journal_year                    2014
_chemical_formula_sum            'C28 H24 O3'
_chemical_formula_weight         408.47
_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                 116.050(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1157(3)
_cell_length_b                   21.1608(4)
_cell_length_c                   10.7272(3)
_cell_measurement_temperature    293(2)
_cell_volume                     2062.95(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12180
_diffrn_reflns_theta_full        66.85
_diffrn_reflns_theta_max         66.85
_diffrn_reflns_theta_min         4.18
_exptl_absorpt_coefficient_mu    0.668
_exptl_absorpt_correction_T_max  0.9362
_exptl_absorpt_correction_T_min  0.8780
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0003(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.873
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3647
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.873
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0365
_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)+(0.1000P)²+0.4655P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1219
_reflns_number_gt                3168
_reflns_number_total             3647
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob00321g2.cif
_cod_data_source_block           04171a
_cod_depositor_comments
'Adding full bibliography for 7153704--7153705.cif.'
_cod_original_cell_volume        2062.95(9)
_cod_original_sg_symbol_H-M      p_1_21/c_1
_cod_database_code               7153704
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
C11 C 0.28087(13) 0.57177(6) 0.16047(13) 0.0225(3) Uani 1 1 d .
C17 C 0.36380(14) 0.69731(6) 0.13396(13) 0.0225(3) Uani 1 1 d .
H17 H 0.4407 0.7248 0.1318 0.027 Uiso 1 1 calc R
C15 C 0.23323(14) 0.61322(6) 0.34560(14) 0.0250(3) Uani 1 1 d .
H15 H 0.2498 0.6431 0.4145 0.030 Uiso 1 1 calc R
C22 C 0.48863(14) 0.70608(6) 0.40496(13) 0.0236(3) Uani 1 1 d .
C10 C 0.31298(13) 0.61551(6) 0.26786(13) 0.0211(3) Uani 1 1 d .
C6 C 0.53127(14) 0.58011(6) 0.16498(14) 0.0256(3) Uani 1 1 d .
H6 H 0.5804 0.5926 0.1078 0.031 Uiso 1 1 calc R
C12 C 0.17645(14) 0.52486(6) 0.13610(14) 0.0267(3) Uani 1 1 d .
H12 H 0.1568 0.4957 0.0652 0.032 Uiso 1 1 calc R
C16 C 0.32349(15) 0.64851(6) 0.01338(13) 0.0246(3) Uani 1 1 d .
H16 H 0.3867 0.6578 -0.0321 0.030 Uiso 1 1 calc R
C21 C 0.16595(16) 0.65026(7) -0.09846(14) 0.0306(3) Uani 1 1 d .
C18 C 0.23930(15) 0.73978(6) 0.12576(14) 0.0275(3) Uani 1 1 d .
C7 C 0.57275(14) 0.62826(6) 0.28712(13) 0.0234(3) Uani 1 1 d .
H7 H 0.6400 0.6599 0.2801 0.028 Uiso 1 1 calc R
C9 C 0.43082(13) 0.66293(6) 0.27710(12) 0.0208(3) Uani 1 1 d .
C24 C 0.57925(17) 0.80814(7) 0.33192(15) 0.0316(3) Uani 1 1 d .
H24 H 0.4970 0.8089 0.2463 0.038 Uiso 1 1 calc R
C28 C 0.71904(16) 0.76061(7) 0.55434(16) 0.0349(3) Uani 1 1 d .
H28 H 0.7305 0.7292 0.6189 0.042 Uiso 1 1 calc R
C14 C 0.12849(14) 0.56596(7) 0.31968(14) 0.0296(3) Uani 1 1 d .
H14 H 0.0760 0.5644 0.3723 0.036 Uiso 1 1 calc R
C23 C 0.59615(15) 0.75962(6) 0.42470(14) 0.0258(3) Uani 1 1 d .
C8 C 0.36385(14) 0.58123(6) 0.07516(13) 0.0243(3) Uani 1 1 d .
H8 H 0.3348 0.5496 0.0012 0.029 Uiso 1 1 calc R
C3 C 0.65881(15) 0.58686(7) 0.41662(14) 0.0302(3) Uani 1 1 d .
H3 H 0.6651 0.6041 0.5039 0.036 Uiso 1 1 calc R
C4 C 0.58445(15) 0.52189(7) 0.37613(15) 0.0318(3) Uani 1 1 d .
H4A H 0.6386 0.4890 0.4416 0.038 Uiso 1 1 calc R
H4B H 0.4828 0.5224 0.3616 0.038 Uiso 1 1 calc R
C13 C 0.10128(15) 0.52138(7) 0.21749(15) 0.0308(3) Uani 1 1 d .
H13 H 0.0333 0.4893 0.2032 0.037 Uiso 1 1 calc R
C5 C 0.59941(15) 0.51778(7) 0.24023(16) 0.0316(3) Uani 1 1 d .
H5 H 0.5577 0.4795 0.1857 0.038 Uiso 1 1 calc R
C19 C 0.10741(17) 0.74702(8) -0.00628(16) 0.0372(4) Uani 1 1 d .
H19 H 0.0457 0.7814 -0.0185 0.045 Uiso 1 1 calc R
C25 C 0.68433(18) 0.85569(7) 0.36578(16) 0.0364(4) Uani 1 1 d .
H25 H 0.6721 0.8879 0.3027 0.044 Uiso 1 1 calc R
C27 C 0.82381(17) 0.80796(8) 0.58757(18) 0.0432(4) Uani 1 1 d .
H27 H 0.9054 0.8078 0.6737 0.052 Uiso 1 1 calc R
C2 C 0.80854(16) 0.57246(8) 0.41644(17) 0.0376(4) Uani 1 1 d .
H2A H 0.8770 0.5541 0.5040 0.045 Uiso 1 1 calc R
H2B H 0.8517 0.6104 0.3991 0.045 Uiso 1 1 calc R
C1 C 0.76768(17) 0.52438(8) 0.29589(18) 0.0396(4) Uani 1 1 d .
H1A H 0.7936 0.5404 0.2248 0.047 Uiso 1 1 calc R
H1B H 0.8166 0.4842 0.3293 0.047 Uiso 1 1 calc R
C26 C 0.80746(17) 0.85523(7) 0.49343(18) 0.0391(4) Uani 1 1 d .
H26 H 0.8785 0.8866 0.5153 0.047 Uiso 1 1 calc R
C20 C 0.07375(17) 0.70566(8) -0.10899(16) 0.0381(4) Uani 1 1 d .
H20 H -0.0114 0.7120 -0.1907 0.046 Uiso 1 1 calc R
O2 O 0.24972(12) 0.76858(5) 0.22807(11) 0.0372(3) Uani 1 1 d .
O1 O 0.11492(13) 0.60704(5) -0.18015(11) 0.0451(3) Uani 1 1 d .
O3 O 0.47051(11) 0.69131(5) 0.50598(10) 0.0317(3) 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 0.0181 0.0091 '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 0.0492 0.0322 '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
C12 C11 C10 120.67(12)
C12 C11 C8 124.28(12)
C10 C11 C8 115.04(11)
C18 C17 C9 108.91(10)
C18 C17 C16 115.79(11)
C9 C17 C16 110.43(10)
C10 C15 C14 119.68(12)
O3 C22 C23 116.48(11)
O3 C22 C9 119.75(11)
C23 C22 C9 122.48(11)
C15 C10 C11 118.91(11)
C15 C10 C9 128.66(11)
C11 C10 C9 112.34(10)
C8 C6 C5 117.22(11)
C8 C6 C7 109.34(10)
C5 C6 C7 102.99(10)
C11 C12 C13 120.06(13)
C21 C16 C8 110.44(10)
C21 C16 C17 116.10(11)
C8 C16 C17 109.25(10)
O1 C21 C20 119.39(13)
O1 C21 C16 121.23(14)
C20 C21 C16 119.38(12)
O2 C18 C19 120.00(13)
O2 C18 C17 120.16(12)
C19 C18 C17 119.84(12)
C3 C7 C6 102.79(11)
C3 C7 C9 117.53(10)
C6 C7 C9 110.20(10)
C10 C9 C22 115.42(10)
C10 C9 C17 104.66(9)
C22 C9 C17 115.65(10)
C10 C9 C7 111.15(10)
C22 C9 C7 103.79(10)
C17 C9 C7 105.89(9)
C23 C24 C25 120.58(14)
C27 C28 C23 120.73(14)
C13 C14 C15 121.23(12)
C24 C23 C28 118.51(13)
C24 C23 C22 126.64(12)
C28 C23 C22 114.73(12)
C11 C8 C6 111.87(10)
C11 C8 C16 105.70(10)
C6 C8 C16 107.07(10)
C4 C3 C2 100.47(12)
C4 C3 C7 103.92(11)
C2 C3 C7 106.01(11)
C5 C4 C3 94.54(11)
C14 C13 C12 119.35(12)
C4 C5 C6 103.96(11)
C4 C5 C1 100.35(12)
C6 C5 C1 106.79(12)
C20 C19 C18 121.69(14)
C26 C25 C24 120.26(14)
C26 C27 C28 120.24(14)
C3 C2 C1 103.16(11)
C5 C1 C2 103.10(11)
C27 C26 C25 119.64(14)
C19 C20 C21 122.55(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C11 C12 1.3881(18)
C11 C10 1.4003(18)
C11 C8 1.5023(18)
C17 C18 1.5180(19)
C17 C9 1.5597(17)
C17 C16 1.5629(17)
C15 C10 1.3927(18)
C15 C14 1.393(2)
C22 O3 1.2166(16)
C22 C23 1.5196(18)
C22 C9 1.5337(17)
C10 C9 1.5276(17)
C6 C8 1.5375(18)
C6 C5 1.542(2)
C6 C7 1.5647(17)
C12 C13 1.389(2)
C16 C21 1.5170(19)
C16 C8 1.5474(18)
C21 O1 1.2139(18)
C21 C20 1.471(2)
C18 O2 1.2187(17)
C18 C19 1.466(2)
C7 C3 1.5470(19)
C7 C9 1.5734(17)
C24 C23 1.387(2)
C24 C25 1.391(2)
C28 C27 1.387(2)
C28 C23 1.401(2)
C14 C13 1.379(2)
C3 C4 1.535(2)
C3 C2 1.546(2)
C4 C5 1.533(2)
C5 C1 1.543(2)
C19 C20 1.329(2)
C25 C26 1.389(2)
C27 C26 1.379(2)
C2 C1 1.552(2)
