#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/26/7152621.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_7152621
loop_
_publ_author_name
'Iaroshenko, Viktor O.'
'Savych, Iryna'
'Villinger, Alexander'
'Sosnovskikh, Vyacheslav Ya'
'Langer, Peter'
_publ_section_title
;
 Reactions of 3-acylchromones with dimethyl 1,3-acetonedicarboxylate and
 1,3-diphenylacetone: one-pot synthesis of functionalized
 2-hydroxybenzophenones, 6H-benzo[c]chromenes and benzo[c]coumarins.
;
_journal_issue                   47
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              9344
_journal_page_last               9348
_journal_paper_doi               10.1039/c2ob07020k
_journal_volume                  10
_journal_year                    2012
_chemical_formula_moiety         'C31 H22 O3, 0.5(C H4 O)'
_chemical_formula_sum            'C31.5 H24 O3.5'
_chemical_formula_weight         458.51
_chemical_name_systematic
;
?
;
_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                 94.710(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5603(5)
_cell_length_b                   8.7419(4)
_cell_length_c                   25.2998(11)
_cell_measurement_reflns_used    3927
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      51.325
_cell_measurement_theta_min      5.671
_cell_volume                     2327.72(18)
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_collection       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_sigmaI/netI    0.0561
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            29004
_diffrn_reflns_theta_full        28.83
_diffrn_reflns_theta_max         28.83
_diffrn_reflns_theta_min         2.97
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9908
_exptl_absorpt_correction_T_min  0.9817
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             964
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_platon_squeeze_details
;
The unit cell contains two methanol molecules which have been treated
as a diffuse contribution to the overall scattering without specific atom
positions by SQUEEZE/PLATON.
;
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         6070
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0527
_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)+(0.0600P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1260
_reflns_number_gt                3908
_reflns_number_total             6070
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c2ob07020k.txt
_cod_data_source_block           av_is2081
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C31.50 H24 O3.50'
_cod_database_code               7152621
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
C1 C 0.08924(13) 0.80320(17) 0.06231(6) 0.0179(3) Uani 1 1 d .
C2 C 0.06528(13) 0.82373(17) 0.11555(6) 0.0174(3) Uani 1 1 d .
C3 C -0.05764(13) 0.80300(17) 0.13147(5) 0.0174(3) Uani 1 1 d .
C4 C -0.15626(13) 0.76627(18) 0.09246(6) 0.0193(3) Uani 1 1 d .
C5 C -0.12974(14) 0.74931(18) 0.03982(6) 0.0194(3) Uani 1 1 d .
H5 H -0.1974 0.7249 0.0141 0.023 Uiso 1 1 calc R
C6 C -0.00821(13) 0.76668(17) 0.02325(6) 0.0175(3) Uani 1 1 d .
C7 C 0.17537(13) 0.86684(18) 0.15392(6) 0.0195(3) Uani 1 1 d .
C8 C 0.23464(15) 1.00770(19) 0.14856(6) 0.0272(4) Uani 1 1 d .
H8 H 0.2038 1.0763 0.1214 0.033 Uiso 1 1 calc R
C9 C 0.33899(17) 1.0482(2) 0.18300(7) 0.0354(4) Uani 1 1 d .
H9 H 0.3792 1.1444 0.1793 0.043 Uiso 1 1 calc R
C10 C 0.38387(16) 0.9481(2) 0.22248(7) 0.0369(5) Uani 1 1 d .
H10 H 0.4561 0.9749 0.2455 0.044 Uiso 1 1 calc R
C11 C 0.32459(16) 0.8103(2) 0.22862(7) 0.0339(4) Uani 1 1 d .
H11 H 0.3547 0.7432 0.2564 0.041 Uiso 1 1 calc R
C12 C 0.22066(15) 0.7684(2) 0.19430(6) 0.0255(4) Uani 1 1 d .
H12 H 0.1806 0.6723 0.1985 0.031 Uiso 1 1 calc R
C13 C -0.08370(14) 0.81104(19) 0.18869(6) 0.0216(3) Uani 1 1 d .
C14 C -0.04376(15) 0.9350(2) 0.22077(6) 0.0271(4) Uani 1 1 d .
H14 H -0.0005 1.0180 0.2060 0.033 Uiso 1 1 calc R
C15 C -0.06672(17) 0.9376(2) 0.27384(7) 0.0356(4) Uani 1 1 d .
H15 H -0.0395 1.0226 0.2953 0.043 Uiso 1 1 calc R
C16 C -0.12898(17) 0.8174(3) 0.29581(7) 0.0410(5) Uani 1 1 d .
H16 H -0.1441 0.8196 0.3323 0.049 Uiso 1 1 calc R
C17 C -0.16935(17) 0.6939(2) 0.26480(7) 0.0371(4) Uani 1 1 d .
H17 H -0.2122 0.6111 0.2799 0.045 Uiso 1 1 calc R
C18 C -0.14704(15) 0.6911(2) 0.21140(6) 0.0280(4) Uani 1 1 d .
H18 H -0.1754 0.6063 0.1901 0.034 Uiso 1 1 calc R
C19 C -0.29251(14) 0.7630(2) 0.10458(6) 0.0233(4) Uani 1 1 d .
C20 C -0.37198(14) 0.6304(2) 0.08790(6) 0.0243(4) Uani 1 1 d .
C21 C -0.50462(15) 0.6367(2) 0.09187(6) 0.0302(4) Uani 1 1 d .
C22 C -0.58051(16) 0.5109(3) 0.07810(7) 0.0398(5) Uani 1 1 d .
H22 H -0.6696 0.5159 0.0809 0.048 Uiso 1 1 calc R
C23 C -0.52701(17) 0.3798(3) 0.06051(8) 0.0415(5) Uani 1 1 d .
H23 H -0.5797 0.2943 0.0511 0.050 Uiso 1 1 calc R
C24 C -0.39652(17) 0.3693(2) 0.05606(7) 0.0352(4) Uani 1 1 d .
H24 H -0.3604 0.2779 0.0436 0.042 Uiso 1 1 calc R
C25 C -0.32067(15) 0.4938(2) 0.07001(6) 0.0278(4) Uani 1 1 d .
H25 H -0.2316 0.4867 0.0674 0.033 Uiso 1 1 calc R
C26 C 0.01412(14) 0.74223(17) -0.03359(6) 0.0183(3) Uani 1 1 d .
C27 C -0.04863(15) 0.62389(18) -0.06210(6) 0.0235(3) Uani 1 1 d .
H27 H -0.1032 0.5575 -0.0448 0.028 Uiso 1 1 calc R
C28 C -0.03227(16) 0.6021(2) -0.11535(6) 0.0280(4) Uani 1 1 d .
H28 H -0.0764 0.5221 -0.1344 0.034 Uiso 1 1 calc R
C29 C 0.04808(16) 0.6965(2) -0.14078(6) 0.0280(4) Uani 1 1 d .
H29 H 0.0598 0.6809 -0.1772 0.034 Uiso 1 1 calc R
C30 C 0.11157(15) 0.81411(19) -0.11313(6) 0.0251(4) Uani 1 1 d .
H30 H 0.1670 0.8791 -0.1306 0.030 Uiso 1 1 calc R
C31 C 0.09412(14) 0.83690(18) -0.05996(6) 0.0204(3) Uani 1 1 d .
H31 H 0.1374 0.9183 -0.0413 0.024 Uiso 1 1 calc R
O1 O 0.20959(10) 0.81173(14) 0.04667(5) 0.0281(3) Uani 1 1 d .
O2 O -0.33722(11) 0.87377(16) 0.12689(5) 0.0369(3) Uani 1 1 d .
O3 O -0.56099(11) 0.76498(19) 0.10874(5) 0.0437(4) Uani 1 1 d .
H1 H 0.268(2) 0.803(3) 0.0744(10) 0.072(8) Uiso 1 1 d .
H2 H -0.495(2) 0.834(3) 0.1207(9) 0.064(7) Uiso 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 0.0033 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
O1 C1 C2 121.18(13)
O1 C1 C6 117.05(13)
C2 C1 C6 121.72(13)
C3 C2 C1 120.25(13)
C3 C2 C7 122.21(13)
C1 C2 C7 117.54(13)
C2 C3 C4 118.41(13)
C2 C3 C13 121.32(12)
C4 C3 C13 120.20(13)
C5 C4 C3 119.91(13)
C5 C4 C19 117.82(13)
C3 C4 C19 121.86(13)
C6 C5 C4 122.70(13)
C6 C5 H5 118.7
C4 C5 H5 118.7
C5 C6 C1 116.99(13)
C5 C6 C26 119.85(13)
C1 C6 C26 123.13(13)
C12 C7 C8 119.26(14)
C12 C7 C2 121.43(14)
C8 C7 C2 119.31(13)
C7 C8 C9 120.15(16)
C7 C8 H8 119.9
C9 C8 H8 119.9
C10 C9 C8 119.88(17)
C10 C9 H9 120.1
C8 C9 H9 120.1
C11 C10 C9 120.31(15)
C11 C10 H10 119.8
C9 C10 H10 119.8
C10 C11 C12 120.28(16)
C10 C11 H11 119.9
C12 C11 H11 119.9
C7 C12 C11 120.10(16)
C7 C12 H12 119.9
C11 C12 H12 119.9
C18 C13 C14 118.42(14)
C18 C13 C3 119.76(14)
C14 C13 C3 121.81(15)
C15 C14 C13 120.50(17)
C15 C14 H14 119.8
C13 C14 H14 119.8
C16 C15 C14 120.34(18)
C16 C15 H15 119.8
C14 C15 H15 119.8
C15 C16 C17 120.09(17)
C15 C16 H16 120.0
C17 C16 H16 120.0
C16 C17 C18 119.75(18)
C16 C17 H17 120.1
C18 C17 H17 120.1
C17 C18 C13 120.89(17)
C17 C18 H18 119.6
C13 C18 H18 119.6
O2 C19 C20 121.21(14)
O2 C19 C4 119.31(15)
C20 C19 C4 119.43(14)
C25 C20 C21 117.85(15)
C25 C20 C19 122.48(14)
C21 C20 C19 119.61(15)
O3 C21 C22 118.37(16)
O3 C21 C20 121.18(16)
C22 C21 C20 120.45(17)
C23 C22 C21 119.99(17)
C23 C22 H22 120.0
C21 C22 H22 120.0
C22 C23 C24 121.22(18)
C22 C23 H23 119.4
C24 C23 H23 119.4
C25 C24 C23 118.96(19)
C25 C24 H24 120.5
C23 C24 H24 120.5
C24 C25 C20 121.53(16)
C24 C25 H25 119.2
C20 C25 H25 119.2
C31 C26 C27 118.28(14)
C31 C26 C6 121.82(13)
C27 C26 C6 119.88(14)
C28 C27 C26 120.80(15)
C28 C27 H27 119.6
C26 C27 H27 119.6
C29 C28 C27 120.12(15)
C29 C28 H28 119.9
C27 C28 H28 119.9
C28 C29 C30 119.93(15)
C28 C29 H29 120.0
C30 C29 H29 120.0
C29 C30 C31 119.94(15)
C29 C30 H30 120.0
C31 C30 H30 120.0
C30 C31 C26 120.92(14)
C30 C31 H31 119.5
C26 C31 H31 119.5
C1 O1 H1 111.3(16)
C21 O3 H2 107.3(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.3639(17)
C1 C2 1.402(2)
C1 C6 1.4038(19)
C2 C3 1.4021(19)
C2 C7 1.5004(19)
C3 C4 1.4117(19)
C3 C13 1.497(2)
C4 C5 1.391(2)
C4 C19 1.496(2)
C5 C6 1.391(2)
C5 H5 0.9500
C6 C26 1.492(2)
C7 C12 1.390(2)
C7 C8 1.393(2)
C8 C9 1.393(2)
C8 H8 0.9500
C9 C10 1.382(3)
C9 H9 0.9500
C10 C11 1.373(3)
C10 H10 0.9500
C11 C12 1.391(2)
C11 H11 0.9500
C12 H12 0.9500
C13 C18 1.393(2)
C13 C14 1.398(2)
C14 C15 1.384(2)
C14 H14 0.9500
C15 C16 1.380(3)
C15 H15 0.9500
C16 C17 1.381(3)
C16 H16 0.9500
C17 C18 1.390(2)
C17 H17 0.9500
C18 H18 0.9500
C19 O2 1.234(2)
C19 C20 1.472(2)
C20 C25 1.402(2)
C20 C21 1.414(2)
C21 O3 1.355(2)
C21 C22 1.388(3)
C22 C23 1.369(3)
C22 H22 0.9500
C23 C24 1.395(3)
C23 H23 0.9500
C24 C25 1.380(2)
C24 H24 0.9500
C25 H25 0.9500
C26 C31 1.392(2)
C26 C27 1.397(2)
C27 C28 1.385(2)
C27 H27 0.9500
C28 C29 1.380(2)
C28 H28 0.9500
C29 C30 1.385(2)
C29 H29 0.9500
C30 C31 1.387(2)
C30 H30 0.9500
C31 H31 0.9500
O1 H1 0.90(2)
O3 H2 0.95(2)
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 -175.13(14)
C6 C1 C2 C3 2.1(2)
O1 C1 C2 C7 4.4(2)
C6 C1 C2 C7 -178.33(14)
C1 C2 C3 C4 -2.1(2)
C7 C2 C3 C4 178.42(14)
C1 C2 C3 C13 174.71(14)
C7 C2 C3 C13 -4.8(2)
C2 C3 C4 C5 0.9(2)
C13 C3 C4 C5 -175.86(14)
C2 C3 C4 C19 -171.57(14)
C13 C3 C4 C19 11.6(2)
C3 C4 C5 C6 0.2(2)
C19 C4 C5 C6 172.98(15)
C4 C5 C6 C1 -0.2(2)
C4 C5 C6 C26 178.16(14)
O1 C1 C6 C5 176.39(14)
C2 C1 C6 C5 -1.0(2)
O1 C1 C6 C26 -1.9(2)
C2 C1 C6 C26 -179.25(14)
C3 C2 C7 C12 65.6(2)
C1 C2 C7 C12 -113.94(17)
C3 C2 C7 C8 -115.30(17)
C1 C2 C7 C8 65.17(19)
C12 C7 C8 C9 0.7(2)
C2 C7 C8 C9 -178.41(15)
C7 C8 C9 C10 0.1(3)
C8 C9 C10 C11 -1.3(3)
C9 C10 C11 C12 1.6(3)
C8 C7 C12 C11 -0.4(2)
C2 C7 C12 C11 178.68(15)
C10 C11 C12 C7 -0.7(3)
C2 C3 C13 C18 -126.90(16)
C4 C3 C13 C18 49.8(2)
C2 C3 C13 C14 51.7(2)
C4 C3 C13 C14 -131.55(16)
C18 C13 C14 C15 0.1(2)
C3 C13 C14 C15 -178.53(14)
C13 C14 C15 C16 0.3(3)
C14 C15 C16 C17 -0.3(3)
C15 C16 C17 C18 0.0(3)
C16 C17 C18 C13 0.4(3)
C14 C13 C18 C17 -0.4(2)
C3 C13 C18 C17 178.23(15)
C5 C4 C19 O2 -121.93(17)
C3 C4 C19 O2 50.7(2)
C5 C4 C19 C20 55.8(2)
C3 C4 C19 C20 -131.53(16)
O2 C19 C20 C25 -169.94(15)
C4 C19 C20 C25 12.4(2)
O2 C19 C20 C21 7.3(2)
C4 C19 C20 C21 -170.36(14)
C25 C20 C21 O3 -179.85(15)
C19 C20 C21 O3 2.8(2)
C25 C20 C21 C22 -0.3(2)
C19 C20 C21 C22 -177.74(15)
O3 C21 C22 C23 179.50(16)
C20 C21 C22 C23 0.0(3)
C21 C22 C23 C24 0.0(3)
C22 C23 C24 C25 0.3(3)
C23 C24 C25 C20 -0.7(3)
C21 C20 C25 C24 0.7(2)
C19 C20 C25 C24 178.04(15)
C5 C6 C26 C31 139.28(15)
C1 C6 C26 C31 -42.5(2)
C5 C6 C26 C27 -39.1(2)
C1 C6 C26 C27 139.12(16)
C31 C26 C27 C28 -0.4(2)
C6 C26 C27 C28 177.99(14)
C26 C27 C28 C29 0.9(2)
C27 C28 C29 C30 -0.6(2)
C28 C29 C30 C31 -0.1(2)
C29 C30 C31 C26 0.5(2)
C27 C26 C31 C30 -0.3(2)
C6 C26 C31 C30 -178.66(14)
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 0.000 1.000 52 15 ' '
2 0.792 0.073 0.674 8 1 ' '
3 0.000 0.500 0.500 52 15 ' '
4 0.292 0.427 0.174 8 1 ' '
5 0.708 0.573 0.826 8 1 ' '
6 0.208 0.927 0.326 8 1 ' '
