#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:17:08 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180176 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/72/7107224.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_7107224
loop_
_publ_author_name
'Dongdong Wu'
'Lei Wang'
'Kai Xu'
'Jia Song'
'Hong-Kun Fun'
'JianHua Xu'
'Yan Zhang'
_publ_section_title
;
 Facile and highly atom-economic method to build biaryl-containing
 medium-ring lactones
;
_journal_name_full               Chem.Commun.
_journal_page_first              1168
_journal_paper_doi               10.1039/c2cc16492b
_journal_volume                  48
_journal_year                    2012
_chemical_formula_sum            'C23 H18 O4'
_chemical_formula_weight         358.37
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_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                 90.0340(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.51370(10)
_cell_length_b                   17.0468(2)
_cell_length_c                   12.05680(10)
_cell_measurement_reflns_used    9925
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      33.62
_cell_measurement_theta_min      2.39
_cell_volume                     1749.82(3)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009)
;
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector diffractometer
;
_diffrn_measurement_method       'φ and ω 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  0.0506
_diffrn_reflns_av_sigmaI/netI    0.0364
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            50813
_diffrn_reflns_theta_full        33.82
_diffrn_reflns_theta_max         33.82
_diffrn_reflns_theta_min         2.07
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9825
_exptl_absorpt_correction_T_min  0.9744
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.619
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         7034
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0553
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0646P)²+0.7063P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1424
_reflns_number_gt                5390
_reflns_number_total             7034
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c2cc16492b.txt
_cod_data_source_block           wdd73a_0m
_cod_database_code               7107224
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 0.52380(10) 0.50241(5) 0.84128(7) 0.02044(17) Uani 1 1 d .
O2 O 0.43683(10) 0.62841(5) 0.84080(7) 0.01710(16) Uani 1 1 d .
O3 O 0.76139(11) 0.71371(5) 0.81002(7) 0.02234(18) Uani 1 1 d .
O4 O 0.71113(10) 0.63070(5) 0.95359(7) 0.01822(16) Uani 1 1 d .
C1 C 0.72441(14) 0.58381(7) 0.52428(9) 0.0196(2) Uani 1 1 d .
H1A H 0.8285 0.5796 0.4965 0.024 Uiso 1 1 calc R
C2 C 0.60307(16) 0.60188(7) 0.45150(10) 0.0219(2) Uani 1 1 d .
H2A H 0.6245 0.6089 0.3748 0.026 Uiso 1 1 calc R
C3 C 0.45072(15) 0.60960(7) 0.49070(10) 0.0210(2) Uani 1 1 d .
H3A H 0.3674 0.6214 0.4410 0.025 Uiso 1 1 calc R
C4 C 0.42066(14) 0.60004(7) 0.60330(10) 0.0187(2) Uani 1 1 d .
H4A H 0.3172 0.6073 0.6309 0.022 Uiso 1 1 calc R
C5 C 0.54198(13) 0.57977(6) 0.67588(9) 0.01557(19) Uani 1 1 d .
C6 C 0.69707(13) 0.57165(6) 0.63750(9) 0.01592(19) Uani 1 1 d .
C7 C 0.83289(13) 0.54869(7) 0.70916(9) 0.0165(2) Uani 1 1 d .
C8 C 0.93103(14) 0.48786(7) 0.67256(10) 0.0205(2) Uani 1 1 d .
H8A H 0.9092 0.4631 0.6036 0.025 Uiso 1 1 calc R
C9 C 1.05930(15) 0.46281(8) 0.73452(11) 0.0230(2) Uani 1 1 d .
H9A H 1.1244 0.4219 0.7072 0.028 Uiso 1 1 calc R
C10 C 1.09263(14) 0.49729(8) 0.83607(11) 0.0227(2) Uani 1 1 d .
H10A H 1.1800 0.4801 0.8787 0.027 Uiso 1 1 calc R
C11 C 0.99663(14) 0.55729(7) 0.87467(10) 0.0202(2) Uani 1 1 d .
H11A H 1.0175 0.5805 0.9448 0.024 Uiso 1 1 calc R
C12 C 0.86952(13) 0.58388(7) 0.81130(9) 0.0170(2) Uani 1 1 d .
C13 C 0.77606(13) 0.65130(7) 0.85520(9) 0.0172(2) Uani 1 1 d .
C14 C 0.58139(14) 0.67815(7) 0.99506(10) 0.0188(2) Uani 1 1 d .
H14A H 0.5826 0.7311 0.9593 0.023 Uiso 1 1 calc R
C15 C 0.43175(13) 0.63287(7) 0.96111(9) 0.0168(2) Uani 1 1 d .
H15A H 0.4324 0.5790 0.9941 0.020 Uiso 1 1 calc R
C16 C 0.50144(13) 0.56383(7) 0.79434(9) 0.01599(19) Uani 1 1 d .
C17 C 0.28530(13) 0.67627(7) 0.99471(9) 0.0163(2) Uani 1 1 d .
C18 C 0.22055(14) 0.66276(7) 1.09937(10) 0.0201(2) Uani 1 1 d .
H18A H 0.2650 0.6241 1.1466 0.024 Uiso 1 1 calc R
C19 C 0.09114(15) 0.70584(8) 1.13453(10) 0.0223(2) Uani 1 1 d .
H19A H 0.0490 0.6972 1.2065 0.027 Uiso 1 1 calc R
C20 C 0.02291(14) 0.76138(7) 1.06520(11) 0.0221(2) Uani 1 1 d .
H20A H -0.0648 0.7911 1.0898 0.027 Uiso 1 1 calc R
C21 C 0.08385(14) 0.77317(7) 0.95962(11) 0.0213(2) Uani 1 1 d .
H21A H 0.0357 0.8099 0.9111 0.026 Uiso 1 1 calc R
C22 C 0.21533(14) 0.73130(7) 0.92470(10) 0.0185(2) Uani 1 1 d .
H22A H 0.2576 0.7402 0.8529 0.022 Uiso 1 1 calc R
C23 C 0.60226(15) 0.68598(8) 1.11932(10) 0.0227(2) Uani 1 1 d .
H23A H 0.7070 0.7070 1.1353 0.034 Uiso 1 1 calc R
H23B H 0.5911 0.6343 1.1541 0.034 Uiso 1 1 calc R
H23C H 0.5223 0.7216 1.1489 0.034 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
C16 O2 C15 117.93(9)
C13 O4 C14 117.77(9)
C2 C1 C6 121.63(11)
C2 C1 H1A 119.2
C6 C1 H1A 119.2
C3 C2 C1 120.06(11)
C3 C2 H2A 120.0
C1 C2 H2A 120.0
C2 C3 C4 119.60(11)
C2 C3 H3A 120.2
C4 C3 H3A 120.2
C3 C4 C5 120.26(11)
C3 C4 H4A 119.9
C5 C4 H4A 119.9
C4 C5 C6 120.82(10)
C4 C5 C16 118.20(10)
C6 C5 C16 120.93(10)
C1 C6 C5 117.57(10)
C1 C6 C7 118.24(10)
C5 C6 C7 124.17(10)
C8 C7 C12 117.35(10)
C8 C7 C6 118.18(10)
C12 C7 C6 124.47(10)
C9 C8 C7 121.73(11)
C9 C8 H8A 119.1
C7 C8 H8A 119.1
C10 C9 C8 120.29(12)
C10 C9 H9A 119.9
C8 C9 H9A 119.9
C9 C10 C11 119.17(11)
C9 C10 H10A 120.4
C11 C10 H10A 120.4
C10 C11 C12 120.67(11)
C10 C11 H11A 119.7
C12 C11 H11A 119.7
C11 C12 C7 120.76(11)
C11 C12 C13 117.85(10)
C7 C12 C13 121.39(10)
O3 C13 O4 125.73(11)
O3 C13 C12 125.12(11)
O4 C13 C12 109.15(10)
O4 C14 C23 107.44(9)
O4 C14 C15 104.88(9)
C23 C14 C15 113.73(10)
O4 C14 H14A 110.2
C23 C14 H14A 110.2
C15 C14 H14A 110.2
O2 C15 C17 108.63(9)
O2 C15 C14 105.41(9)
C17 C15 C14 111.48(9)
O2 C15 H15A 110.4
C17 C15 H15A 110.4
C14 C15 H15A 110.4
O1 C16 O2 125.23(10)
O1 C16 C5 124.77(10)
O2 C16 C5 110.00(9)
C22 C17 C18 119.27(11)
C22 C17 C15 121.39(10)
C18 C17 C15 119.31(10)
C19 C18 C17 120.11(11)
C19 C18 H18A 119.9
C17 C18 H18A 119.9
C20 C19 C18 120.49(11)
C20 C19 H19A 119.8
C18 C19 H19A 119.8
C21 C20 C19 119.55(11)
C21 C20 H20A 120.2
C19 C20 H20A 120.2
C20 C21 C22 120.22(11)
C20 C21 H21A 119.9
C22 C21 H21A 119.9
C21 C22 C17 120.30(11)
C21 C22 H22A 119.9
C17 C22 H22A 119.9
C14 C23 H23A 109.5
C14 C23 H23B 109.5
H23A C23 H23B 109.5
C14 C23 H23C 109.5
H23A C23 H23C 109.5
H23B C23 H23C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C16 1.2053(14)
O2 C16 1.3522(14)
O2 C15 1.4532(13)
O3 C13 1.2017(15)
O4 C13 1.3553(14)
O4 C14 1.4577(14)
C1 C2 1.3896(17)
C1 C6 1.4003(16)
C1 H1A 0.9500
C2 C3 1.3870(18)
C2 H2A 0.9500
C3 C4 1.3912(17)
C3 H3A 0.9500
C4 C5 1.3967(16)
C4 H4A 0.9500
C5 C6 1.4062(16)
C5 C16 1.4945(16)
C6 C7 1.4951(16)
C7 C8 1.4031(17)
C7 C12 1.4048(16)
C8 C9 1.3900(17)
C8 H8A 0.9500
C9 C10 1.3872(19)
C9 H9A 0.9500
C10 C11 1.3897(18)
C10 H10A 0.9500
C11 C12 1.3998(16)
C11 H11A 0.9500
C12 C13 1.4950(16)
C14 C23 1.5144(17)
C14 C15 1.5447(17)
C14 H14A 1.0000
C15 C17 1.5056(16)
C15 H15A 1.0000
C17 C22 1.3952(16)
C17 C18 1.3964(16)
C18 C19 1.3905(17)
C18 H18A 0.9500
C19 C20 1.3899(18)
C19 H19A 0.9500
C20 C21 1.3896(18)
C20 H20A 0.9500
C21 C22 1.3930(17)
C21 H21A 0.9500
C22 H22A 0.9500
C23 H23A 0.9800
C23 H23B 0.9800
C23 H23C 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C15 H15A O1 1.0000 2.4500 3.3372(14) 147.00 3_667 yes
C23 H23A O3 0.9800 2.5500 3.1689(15) 121.00 4_565 yes
C23 H23B O1 0.9800 2.5300 3.4193(16) 151.00 3_667 yes
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
C6 C1 C2 C3 1.12(19)
C1 C2 C3 C4 0.72(19)
C2 C3 C4 C5 -2.49(18)
C3 C4 C5 C6 2.46(17)
C3 C4 C5 C16 -175.12(11)
C2 C1 C6 C5 -1.14(17)
C2 C1 C6 C7 177.13(11)
C4 C5 C6 C1 -0.64(16)
C16 C5 C6 C1 176.88(10)
C4 C5 C6 C7 -178.80(11)
C16 C5 C6 C7 -1.28(17)
C1 C6 C7 C8 -47.97(15)
C5 C6 C7 C8 130.18(12)
C1 C6 C7 C12 132.07(12)
C5 C6 C7 C12 -49.78(17)
C12 C7 C8 C9 0.24(17)
C6 C7 C8 C9 -179.72(11)
C7 C8 C9 C10 0.75(19)
C8 C9 C10 C11 -0.27(19)
C9 C10 C11 C12 -1.22(19)
C10 C11 C12 C7 2.25(18)
C10 C11 C12 C13 -176.96(11)
C8 C7 C12 C11 -1.72(16)
C6 C7 C12 C11 178.24(11)
C8 C7 C12 C13 177.46(10)
C6 C7 C12 C13 -2.58(17)
C14 O4 C13 O3 17.16(16)
C14 O4 C13 C12 -162.87(9)
C11 C12 C13 O3 118.53(13)
C7 C12 C13 O3 -60.67(16)
C11 C12 C13 O4 -61.44(13)
C7 C12 C13 O4 119.36(11)
C13 O4 C14 C23 -140.96(10)
C13 O4 C14 C15 97.71(11)
C16 O2 C15 C17 -146.61(10)
C16 O2 C15 C14 93.81(11)
O4 C14 C15 O2 -60.24(11)
C23 C14 C15 O2 -177.34(9)
O4 C14 C15 C17 -177.91(9)
C23 C14 C15 C17 64.98(13)
C15 O2 C16 O1 17.39(16)
C15 O2 C16 C5 -162.37(9)
C4 C5 C16 O1 119.47(13)
C6 C5 C16 O1 -58.11(16)
C4 C5 C16 O2 -60.77(13)
C6 C5 C16 O2 121.65(11)
O2 C15 C17 C22 -26.77(14)
C14 C15 C17 C22 88.95(13)
O2 C15 C17 C18 155.01(10)
C14 C15 C17 C18 -89.27(13)
C22 C17 C18 C19 -2.28(18)
C15 C17 C18 C19 175.98(11)
C17 C18 C19 C20 1.44(19)
C18 C19 C20 C21 0.67(19)
C19 C20 C21 C22 -1.92(19)
C20 C21 C22 C17 1.07(18)
C18 C17 C22 C21 1.03(17)
C15 C17 C22 C21 -177.19(11)
