#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:40:09 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178476 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/97/4029780.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_4029780
loop_
_publ_author_name
'Arimura, Junya'
'Mizuta, Tsutomu'
'Hiraga, Yoshikazu'
'Abe, Manabu'
_publ_section_title
;
 Formation of macrocyclic lactones in the Paternò-Büchi dimerization
 reaction.
;
_journal_name_full               'Beilstein journal of organic chemistry'
_journal_page_first              265
_journal_page_last               269
_journal_paper_doi               10.3762/bjoc.7.35
_journal_volume                  7
_journal_year                    2011
_chemical_formula_sum            'C26 H20 O8'
_chemical_formula_weight         460.42
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                62.3560(10)
_cell_angle_beta                 89.0080(10)
_cell_angle_gamma                89.8930(10)
_cell_formula_units_Z            2
_cell_length_a                   9.2883(9)
_cell_length_b                   11.2794(11)
_cell_length_c                   11.6730(12)
_cell_measurement_reflns_used    3905
_cell_measurement_temperature    173
_cell_measurement_theta_max      28.47
_cell_measurement_theta_min      2.19
_cell_volume                     1083.15(19)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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  0.0125
_diffrn_reflns_av_sigmaI/netI    0.0205
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5138
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.9947
_exptl_absorpt_correction_T_min  0.9766
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         3721
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.984
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0356
_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)+(0.0712P)²+0.2916P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1060
_reflns_number_gt                3373
_reflns_number_total             3721
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1860-5397-7-35-S2.cif
_cod_data_source_block           20100706aj389
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/Beilstein/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4029780
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 0.27133(15) 0.74856(13) 0.25280(12) 0.0261(3) Uani 1 1 d
C2 C 0.16720(17) 0.82331(15) 0.27770(14) 0.0342(3) Uani 1 1 d
C3 C 0.04667(18) 0.86754(16) 0.20150(15) 0.0385(4) Uani 1 1 d
C4 C 0.02988(17) 0.83819(15) 0.09934(14) 0.0374(4) Uani 1 1 d
C5 C 0.13411(17) 0.76762(15) 0.07230(14) 0.0364(3) Uani 1 1 d
C6 C 0.25529(16) 0.72144(14) 0.14937(13) 0.0316(3) Uani 1 1 d
C7 C 0.26096(15) 0.37570(14) 0.61461(13) 0.0286(3) Uani 1 1 d
C8 C 0.34046(14) 0.59672(13) 0.47566(12) 0.0257(3) Uani 1 1 d
C9 C 0.39868(15) 0.69315(13) 0.34102(13) 0.0262(3) Uani 1 1 d
C10 C 0.51465(15) 0.79007(13) 0.34503(14) 0.0291(3) Uani 1 1 d
C11 C 0.61951(15) 0.71059(13) 0.30385(13) 0.0281(3) Uani 1 1 d
C12 C 0.52318(18) 0.92605(15) 0.23034(16) 0.0391(4) Uani 1 1 d
C13 C 0.61564(18) 0.92328(15) 0.14599(16) 0.0415(4) Uani 1 1 d
C15 C 0.34270(16) 0.32245(15) 0.28181(14) 0.0328(3) Uani 1 1 d
C16 C 0.46641(17) 0.36661(15) 0.20648(14) 0.0363(3) Uani 1 1 d
C17 C 0.48741(17) 0.34002(15) 0.10253(14) 0.0363(3) Uani 1 1 d
C18 C 0.38297(17) 0.27234(15) 0.07284(14) 0.0366(3) Uani 1 1 d
C19 C 0.25837(16) 0.22658(14) 0.14914(13) 0.0320(3) Uani 1 1 d
C20 C 0.23865(15) 0.25049(13) 0.25469(12) 0.0264(3) Uani 1 1 d
C21 C 0.23461(15) -0.12545(14) 0.61326(13) 0.0287(3) Uani 1 1 d
C22 C 0.16043(14) 0.09636(13) 0.47688(12) 0.0264(3) Uani 1 1 d
C23 C 0.10783(15) 0.19440(13) 0.34297(13) 0.0265(3) Uani 1 1 d
C24 C -0.00828(15) 0.29028(13) 0.34946(14) 0.0288(3) Uani 1 1 d
C25 C -0.11180(15) 0.21254(13) 0.30625(13) 0.0283(3) Uani 1 1 d
C26 C -0.01280(18) 0.42770(15) 0.23733(16) 0.0383(4) Uani 1 1 d
C27 C -0.10248(18) 0.42757(15) 0.15219(16) 0.0408(4) Uani 1 1 d
H1 H 0.1816(18) 0.8429(17) 0.3502(17) 0.041(4) Uiso 1 1 d
H2 H -0.026(2) 0.9150(18) 0.2198(16) 0.043(5) Uiso 1 1 d
H3 H -0.055(2) 0.8667(18) 0.0490(17) 0.046(5) Uiso 1 1 d
H4 H 0.1254(19) 0.7510(18) 0.0013(18) 0.046(5) Uiso 1 1 d
H5 H 0.3268(19) 0.6709(18) 0.1323(16) 0.041(4) Uiso 1 1 d
H6 H 0.1903(18) 0.3235(17) 0.5967(16) 0.037(4) Uiso 1 1 d
H7 H 0.2136(17) 0.4229(16) 0.6576(15) 0.032(4) Uiso 1 1 d
H8 H 0.5238(17) 0.7869(16) 0.4292(16) 0.035(4) Uiso 1 1 d
H9 H 0.470(2) 1.000(2) 0.2213(18) 0.048(5) Uiso 1 1 d
H10 H 0.648(2) 0.992(2) 0.0621(19) 0.056(5) Uiso 1 1 d
H11 H 0.3282(18) 0.3410(17) 0.3537(17) 0.042(4) Uiso 1 1 d
H12 H 0.539(2) 0.4142(18) 0.2254(17) 0.044(5) Uiso 1 1 d
H13 H 0.5743(18) 0.3691(16) 0.0517(16) 0.035(4) Uiso 1 1 d
H14 H 0.3968(18) 0.2572(17) -0.0006(17) 0.042(4) Uiso 1 1 d
H15 H 0.1858(18) 0.1781(17) 0.1304(16) 0.036(4) Uiso 1 1 d
H16 H 0.2821(17) -0.0811(16) 0.6568(15) 0.034(4) Uiso 1 1 d
H17 H 0.3055(17) -0.1770(16) 0.5933(14) 0.028(4) Uiso 1 1 d
H18 H -0.0233(17) 0.2848(16) 0.4335(16) 0.033(4) Uiso 1 1 d
H19 H 0.040(2) 0.502(2) 0.2299(18) 0.050(5) Uiso 1 1 d
H20 H -0.1330(19) 0.4981(19) 0.0701(18) 0.046(5) Uiso 1 1 d
O1 O 0.32143(10) 0.47262(9) 0.49090(9) 0.0275(2) Uani 1 1 d
O2 O 0.30863(12) 0.63276(10) 0.55471(9) 0.0352(3) Uani 1 1 d
O3 O 0.50466(10) 0.63193(9) 0.29216(9) 0.0281(2) Uani 1 1 d
O4 O 0.68189(11) 0.80064(10) 0.18197(9) 0.0369(3) Uani 1 1 d
O5 O 0.17902(10) -0.02725(9) 0.49043(9) 0.0280(2) Uani 1 1 d
O6 O 0.18931(12) 0.13090(10) 0.55690(9) 0.0358(3) Uani 1 1 d
O7 O 0.00359(10) 0.13500(9) 0.29247(9) 0.0290(2) Uani 1 1 d
O8 O -0.16953(12) 0.30516(11) 0.18525(9) 0.0375(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 0.0033 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C6 C1 C2 119.71(13) . .
C6 C1 C9 120.08(12) . .
C2 C1 C9 120.18(12) . .
C3 C2 C1 120.20(14) . .
C3 C2 H1 121.4(10) . .
C1 C2 H1 118.4(10) . .
C2 C3 C4 119.87(15) . .
C2 C3 H2 120.6(11) . .
C4 C3 H2 119.5(11) . .
C5 C4 C3 120.12(14) . .
C5 C4 H3 120.7(11) . .
C3 C4 H3 119.2(11) . .
C4 C5 C6 120.41(14) . .
C4 C5 H4 120.5(11) . .
C6 C5 H4 119.1(11) . .
C1 C6 C5 119.65(14) . .
C1 C6 H5 119.5(10) . .
C5 C6 H5 120.8(10) . .
O1 C7 C11 108.64(11) . 2_666
O1 C7 H6 106.9(10) . .
C11 C7 H6 111.5(10) 2_666 .
O1 C7 H7 109.5(9) . .
C11 C7 H7 110.4(9) 2_666 .
H6 C7 H7 109.7(13) . .
O2 C8 O1 124.99(12) . .
O2 C8 C9 122.38(12) . .
O1 C8 C9 112.50(10) . .
O3 C9 C1 112.63(10) . .
O3 C9 C8 112.86(10) . .
C1 C9 C8 107.73(11) . .
O3 C9 C10 90.88(10) . .
C1 C9 C10 119.82(11) . .
C8 C9 C10 112.27(11) . .
C12 C10 C11 101.53(12) . .
C12 C10 C9 116.35(12) . .
C11 C10 C9 84.60(9) . .
C12 C10 H8 116.2(10) . .
C11 C10 H8 119.8(10) . .
C9 C10 H8 114.0(10) . .
O4 C11 O3 112.48(10) . .
O4 C11 C7 107.00(11) . 2_666
O3 C11 C7 111.77(11) . 2_666
O4 C11 C10 107.98(11) . .
O3 C11 C10 92.17(10) . .
C7 C11 C10 124.86(12) 2_666 .
C13 C12 C10 109.04(14) . .
C13 C12 H9 126.0(11) . .
C10 C12 H9 124.9(11) . .
C12 C13 O4 115.33(14) . .
C12 C13 H10 131.9(12) . .
O4 C13 H10 112.8(12) . .
C16 C15 C20 120.38(13) . .
C16 C15 H11 119.9(10) . .
C20 C15 H11 119.8(10) . .
C15 C16 C17 119.93(14) . .
C15 C16 H12 121.1(11) . .
C17 C16 H12 119.0(11) . .
C18 C17 C16 119.98(14) . .
C18 C17 H13 120.3(9) . .
C16 C17 H13 119.7(9) . .
C17 C18 C19 120.33(14) . .
C17 C18 H14 119.4(10) . .
C19 C18 H14 120.3(10) . .
C20 C19 C18 119.75(14) . .
C20 C19 H15 119.1(10) . .
C18 C19 H15 121.1(10) . .
C19 C20 C15 119.59(13) . .
C19 C20 C23 120.28(12) . .
C15 C20 C23 120.09(11) . .
O5 C21 C25 108.51(11) . 2_556
O5 C21 H16 110.3(10) . .
C25 C21 H16 111.5(9) 2_556 .
O5 C21 H17 106.3(9) . .
C25 C21 H17 111.3(9) 2_556 .
H16 C21 H17 108.9(13) . .
O6 C22 O5 124.95(13) . .
O6 C22 C23 122.30(12) . .
O5 C22 C23 112.61(10) . .
O7 C23 C20 112.48(10) . .
O7 C23 C22 112.97(10) . .
C20 C23 C22 107.83(11) . .
O7 C23 C24 90.89(10) . .
C20 C23 C24 120.07(11) . .
C22 C23 C24 111.94(11) . .
C26 C24 C25 101.74(12) . .
C26 C24 C23 116.66(11) . .
C25 C24 C23 84.59(9) . .
C26 C24 H18 115.9(10) . .
C25 C24 H18 118.4(9) . .
C23 C24 H18 115.0(10) . .
O8 C25 O7 112.66(10) . .
O8 C25 C21 106.96(12) . 2_556
O7 C25 C21 111.81(11) . 2_556
O8 C25 C24 107.74(11) . .
O7 C25 C24 92.09(10) . .
C21 C25 C24 125.01(11) 2_556 .
C27 C26 C24 109.00(14) . .
C27 C26 H19 125.7(12) . .
C24 C26 H19 125.3(12) . .
C26 C27 O8 115.35(14) . .
C26 C27 H20 131.6(11) . .
O8 C27 H20 113.1(11) . .
C8 O1 C7 116.09(10) . .
C11 O3 C9 92.00(9) . .
C13 O4 C11 106.02(11) . .
C22 O5 C21 116.16(10) . .
C25 O7 C23 92.08(9) . .
C27 O8 C25 106.08(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.3866(19) .
C1 C2 1.395(2) .
C1 C9 1.5140(19) .
C2 C3 1.383(2) .
C2 H1 0.980(17) .
C3 C4 1.389(2) .
C3 H2 0.939(18) .
C4 C5 1.375(2) .
C4 H3 0.956(19) .
C5 C6 1.395(2) .
C5 H4 0.935(18) .
C6 H5 0.951(18) .
C7 O1 1.4510(16) .
C7 C11 1.503(2) 2_666
C7 H6 0.970(17) .
C7 H7 0.984(16) .
C8 O2 1.2009(16) .
C8 O1 1.3383(16) .
C8 C9 1.5271(18) .
C9 O3 1.4542(16) .
C9 C10 1.5528(18) .
C10 C12 1.498(2) .
C10 C11 1.5374(19) .
C10 H8 0.971(17) .
C11 O4 1.4228(16) .
C11 O3 1.4369(16) .
C11 C7 1.503(2) 2_666
C12 C13 1.307(3) .
C12 H9 0.93(2) .
C13 O4 1.391(2) .
C13 H10 0.97(2) .
C15 C16 1.379(2) .
C15 C20 1.395(2) .
C15 H11 0.962(18) .
C16 C17 1.389(2) .
C16 H12 0.954(18) .
C17 C18 1.380(2) .
C17 H13 0.957(17) .
C18 C19 1.392(2) .
C18 H14 0.956(17) .
C19 C20 1.3874(19) .
C19 H15 0.959(17) .
C20 C23 1.5143(19) .
C21 O5 1.4488(17) .
C21 C25 1.503(2) 2_556
C21 H16 0.974(16) .
C21 H17 0.972(16) .
C22 O6 1.2012(16) .
C22 O5 1.3395(16) .
C22 C23 1.5249(19) .
C23 O7 1.4569(15) .
C23 C24 1.5516(19) .
C24 C26 1.495(2) .
C24 C25 1.5421(19) .
C24 H18 0.961(16) .
C25 O8 1.4243(17) .
C25 O7 1.4355(16) .
C25 C21 1.503(2) 2_556
C26 C27 1.308(3) .
C26 H19 0.93(2) .
C27 O8 1.3942(19) .
C27 H20 0.966(19) .
