#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:51:30 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180319 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/33/7153309.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_7153309
loop_
_publ_author_name
'Xie, Fuchun'
'Pan, Xuan'
'Lin, Shijun'
'Hu, Youhong'
_publ_section_title
;
 A base-promoted desalicyloylative dimerization of 3-(1-alkynyl)chromones:
 an unusual approach to 2-alkynyl xanthones.
;
_journal_issue                   6
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1378
_journal_page_last               1381
_journal_paper_doi               10.1039/b925234g
_journal_volume                  8
_journal_year                    2010
_chemical_formula_sum            'C21 H14 O4'
_chemical_formula_weight         330.32
_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                 94.579(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.377(2)
_cell_length_b                   15.318(2)
_cell_length_c                   8.3322(14)
_cell_measurement_reflns_used    1919
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      49.148
_cell_measurement_theta_min      5.319
_cell_volume                     1574.7(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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.1184
_diffrn_reflns_av_sigmaI/netI    0.0840
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8210
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75675
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.403
_exptl_crystal_size_mid          0.347
_exptl_crystal_size_min          0.112
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.877
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         2932
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.877
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0470
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0517P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1152
_reflns_number_gt                1814
_reflns_number_total             2932
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b925234g.txt
_cod_data_source_block           cd29342
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        1574.6(4)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7153309
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 0.11523(10) 0.08830(12) 0.17278(16) 0.0885(5) Uani 1 1 d .
O2 O -0.03009(11) 0.10741(13) 0.3780(2) 0.0950(6) Uani 1 1 d D
O3 O 0.47072(12) 0.25136(11) -0.0370(2) 0.0973(5) Uani 1 1 d .
O4 O 0.62249(9) 0.03559(8) 0.16481(13) 0.0568(3) Uani 1 1 d .
C1 C 0.18672(14) 0.09363(13) 0.2833(2) 0.0572(5) Uani 1 1 d .
C2 C 0.16244(13) 0.11806(11) 0.44630(19) 0.0494(4) Uani 1 1 d .
C3 C 0.24426(14) 0.13755(12) 0.5652(2) 0.0543(5) Uani 1 1 d .
H3 H 0.3161 0.1356 0.5403 0.065 Uiso 1 1 calc R
C4 C 0.22130(16) 0.15953(13) 0.7183(2) 0.0660(5) Uani 1 1 d .
H4 H 0.2770 0.1719 0.7966 0.079 Uiso 1 1 calc R
C5 C 0.11498(17) 0.16311(14) 0.7548(2) 0.0733(6) Uani 1 1 d .
H5 H 0.0989 0.1781 0.8584 0.088 Uiso 1 1 calc R
C6 C 0.03264(16) 0.14497(14) 0.6406(2) 0.0751(6) Uani 1 1 d .
H6 H -0.0388 0.1472 0.6673 0.090 Uiso 1 1 calc R
C7 C 0.05475(14) 0.12349(13) 0.4863(2) 0.0617(5) Uani 1 1 d .
C8 C 0.30260(13) 0.07664(12) 0.24948(18) 0.0501(4) Uani 1 1 d .
C9 C 0.35256(14) 0.13369(12) 0.15270(19) 0.0542(5) Uani 1 1 d .
H9 H 0.3131 0.1804 0.1072 0.065 Uiso 1 1 calc R
C10 C 0.46075(13) 0.12402(11) 0.12008(19) 0.0497(4) Uani 1 1 d .
C11 C 0.51556(13) 0.05168(11) 0.18617(18) 0.0470(4) Uani 1 1 d .
C12 C 0.46544(13) -0.00803(12) 0.27965(19) 0.0522(4) Uani 1 1 d .
H12 H 0.5038 -0.0565 0.3200 0.063 Uiso 1 1 calc R
C13 C 0.35918(13) 0.00327(12) 0.31403(18) 0.0499(4) Uani 1 1 d .
C14 C 0.51626(15) 0.18703(14) 0.0242(2) 0.0611(5) Uani 1 1 d .
C15 C 0.63119(14) 0.16847(12) 0.00924(19) 0.0534(5) Uani 1 1 d .
C16 C 0.69575(16) 0.22410(14) -0.0751(2) 0.0666(5) Uani 1 1 d .
H16 H 0.6650 0.2734 -0.1255 0.080 Uiso 1 1 calc R
C17 C 0.80385(17) 0.20710(16) -0.0848(2) 0.0767(6) Uani 1 1 d .
H17 H 0.8465 0.2453 -0.1391 0.092 Uiso 1 1 calc R
C18 C 0.84882(16) 0.13268(17) -0.0129(2) 0.0764(6) Uani 1 1 d .
H18 H 0.9220 0.1209 -0.0202 0.092 Uiso 1 1 calc R
C19 C 0.78738(14) 0.07611(15) 0.0687(2) 0.0659(6) Uani 1 1 d .
H19 H 0.8180 0.0259 0.1159 0.079 Uiso 1 1 calc R
C20 C 0.67915(13) 0.09497(13) 0.07947(18) 0.0513(4) Uani 1 1 d .
C21 C 0.30684(15) -0.06332(13) 0.4149(2) 0.0669(5) Uani 1 1 d .
H21A H 0.3505 -0.1152 0.4226 0.100 Uiso 1 1 calc R
H21B H 0.2361 -0.0773 0.3660 0.100 Uiso 1 1 calc R
H21C H 0.3004 -0.0401 0.5208 0.100 Uiso 1 1 calc R
H2 H -0.0036(19) 0.0974(17) 0.287(2) 0.116(10) Uiso 1 1 d D
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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
C7 O2 H2 106.8(16)
C11 O4 C20 118.93(14)
O1 C1 C2 121.60(16)
O1 C1 C8 119.24(15)
C2 C1 C8 119.14(14)
C3 C2 C7 118.02(16)
C3 C2 C1 121.61(15)
C7 C2 C1 120.36(15)
C4 C3 C2 121.48(16)
C4 C3 H3 119.3
C2 C3 H3 119.3
C3 C4 C5 119.24(18)
C3 C4 H4 120.4
C5 C4 H4 120.4
C6 C5 C4 120.79(18)
C6 C5 H5 119.6
C4 C5 H5 119.6
C5 C6 C7 120.43(18)
C5 C6 H6 119.8
C7 C6 H6 119.8
O2 C7 C6 117.75(17)
O2 C7 C2 122.24(17)
C6 C7 C2 120.00(17)
C9 C8 C13 120.00(16)
C9 C8 C1 118.77(16)
C13 C8 C1 121.23(16)
C8 C9 C10 122.16(16)
C8 C9 H9 118.9
C10 C9 H9 118.9
C11 C10 C9 116.94(16)
C11 C10 C14 120.53(16)
C9 C10 C14 122.52(16)
O4 C11 C12 115.84(15)
O4 C11 C10 122.50(16)
C12 C11 C10 121.65(16)
C13 C12 C11 120.87(16)
C13 C12 H12 119.6
C11 C12 H12 119.6
C12 C13 C8 118.31(16)
C12 C13 C21 119.50(16)
C8 C13 C21 122.17(16)
O3 C14 C10 122.56(17)
O3 C14 C15 122.54(18)
C10 C14 C15 114.89(16)
C20 C15 C16 117.85(17)
C20 C15 C14 120.62(17)
C16 C15 C14 121.53(18)
C17 C16 C15 120.9(2)
C17 C16 H16 119.5
C15 C16 H16 119.5
C16 C17 C18 119.4(2)
C16 C17 H17 120.3
C18 C17 H17 120.3
C19 C18 C17 121.1(2)
C19 C18 H18 119.5
C17 C18 H18 119.5
C18 C19 C20 118.7(2)
C18 C19 H19 120.6
C20 C19 H19 120.6
O4 C20 C19 115.56(17)
O4 C20 C15 122.47(15)
C19 C20 C15 121.97(17)
C13 C21 H21A 109.5
C13 C21 H21B 109.5
H21A C21 H21B 109.5
C13 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2277(18)
O2 C7 1.351(2)
O2 H2 0.859(16)
O3 C14 1.226(2)
O4 C11 1.3717(19)
O4 C20 1.380(2)
C1 C2 1.463(2)
C1 C8 1.506(2)
C2 C3 1.392(2)
C2 C7 1.402(2)
C3 C4 1.371(2)
C3 H3 0.9300
C4 C5 1.375(3)
C4 H4 0.9300
C5 C6 1.366(3)
C5 H5 0.9300
C6 C7 1.376(3)
C6 H6 0.9300
C8 C9 1.370(2)
C8 C13 1.408(2)
C9 C10 1.395(2)
C9 H9 0.9300
C10 C11 1.390(2)
C10 C14 1.459(3)
C11 C12 1.380(2)
C12 C13 1.379(2)
C12 H12 0.9300
C13 C21 1.501(2)
C14 C15 1.466(2)
C15 C20 1.381(3)
C15 C16 1.396(3)
C16 C17 1.372(3)
C16 H16 0.9300
C17 C18 1.384(3)
C17 H17 0.9300
C18 C19 1.369(3)
C18 H18 0.9300
C19 C20 1.380(2)
C19 H19 0.9300
C21 H21A 0.9600
C21 H21B 0.9600
C21 H21C 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
O1 C1 C2 C3 -169.68(18)
C8 C1 C2 C3 8.9(3)
O1 C1 C2 C7 9.5(3)
C8 C1 C2 C7 -171.91(17)
C7 C2 C3 C4 1.5(3)
C1 C2 C3 C4 -179.30(19)
C2 C3 C4 C5 -0.6(3)
C3 C4 C5 C6 0.1(3)
C4 C5 C6 C7 -0.6(3)
C5 C6 C7 O2 -179.10(19)
C5 C6 C7 C2 1.5(3)
C3 C2 C7 O2 178.71(18)
C1 C2 C7 O2 -0.5(3)
C3 C2 C7 C6 -1.9(3)
C1 C2 C7 C6 178.83(19)
O1 C1 C8 C9 66.8(2)
C2 C1 C8 C9 -111.85(19)
O1 C1 C8 C13 -112.6(2)
C2 C1 C8 C13 68.8(2)
C13 C8 C9 C10 -2.8(2)
C1 C8 C9 C10 177.85(15)
C8 C9 C10 C11 2.1(2)
C8 C9 C10 C14 -176.64(16)
C20 O4 C11 C12 -176.77(13)
C20 O4 C11 C10 2.4(2)
C9 C10 C11 O4 -179.05(14)
C14 C10 C11 O4 -0.3(2)
C9 C10 C11 C12 0.1(2)
C14 C10 C11 C12 178.84(15)
O4 C11 C12 C13 177.64(14)
C10 C11 C12 C13 -1.6(2)
C11 C12 C13 C8 0.9(2)
C11 C12 C13 C21 179.49(15)
C9 C8 C13 C12 1.2(2)
C1 C8 C13 C12 -179.41(15)
C9 C8 C13 C21 -177.33(15)
C1 C8 C13 C21 2.0(2)
C11 C10 C14 O3 179.55(18)
C9 C10 C14 O3 -1.8(3)
C11 C10 C14 C15 -1.6(2)
C9 C10 C14 C15 177.08(15)
O3 C14 C15 C20 -179.69(19)
C10 C14 C15 C20 1.5(2)
O3 C14 C15 C16 0.6(3)
C10 C14 C15 C16 -178.24(16)
C20 C15 C16 C17 -1.4(3)
C14 C15 C16 C17 178.36(17)
C15 C16 C17 C18 1.5(3)
C16 C17 C18 C19 -0.5(3)
C17 C18 C19 C20 -0.5(3)
C11 O4 C20 C19 177.46(14)
C11 O4 C20 C15 -2.6(2)
C18 C19 C20 O4 -179.36(15)
C18 C19 C20 C15 0.7(3)
C16 C15 C20 O4 -179.70(14)
C14 C15 C20 O4 0.6(2)
C16 C15 C20 C19 0.3(3)
C14 C15 C20 C19 -179.45(16)
