#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/67/1516776.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_1516776
loop_
_publ_author_name
'Wright, Nathan E.'
'ElSohly, Adel M.'
'Snyder, Scott A.'
_publ_section_title
;
 Syntheses of Cyclotriveratrylene Analogues and Their Long Elusive
 Triketone Congeners.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3644
_journal_paper_doi               10.1021/ol501284s
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C27 H26 O8'
_chemical_formula_weight         478.48
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 96.2678(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.7447(14)
_cell_length_b                   11.7233(13)
_cell_length_c                   15.8897(18)
_cell_measurement_reflns_used    9846
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      32.89
_cell_measurement_theta_min      2.37
_cell_volume                     2359.9(5)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            41391
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.025
_diffrn_reflns_theta_min         1.948
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.5926
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.542
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         8535
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0446
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0783P)²+0.5065P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1227
_refine_ls_wR_factor_ref         0.1316
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7112
_reflns_number_total             8535
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol501284s_si_003.cif
_cod_data_source_block           s
_cod_depositor_comments
'Adding full bibliography for 1516775--1516777.cif.'
_cod_database_code               1516776
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.970
_shelx_estimated_absorpt_t_max   0.990
_shelxl_version_number           2013-4
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.69631(6) 0.22430(8) 0.45966(5) 0.02623(17) Uani 1 1 d . .
O2 O 0.41323(5) 0.18017(7) 0.23515(5) 0.02614(16) Uani 1 1 d . .
O3 O 0.71696(5) 0.00974(7) 0.12314(4) 0.02054(14) Uani 1 1 d . .
O4 O 0.86000(5) -0.04834(6) 0.29678(4) 0.01914(14) Uani 1 1 d . .
O5 O 1.11385(6) 0.01353(7) 0.06782(5) 0.02602(16) Uani 1 1 d . .
O6 O 1.01758(6) 0.37905(6) 0.16337(5) 0.02274(15) Uani 1 1 d . .
O7 O 1.18895(5) 0.22564(7) 0.48038(5) 0.02256(15) Uani 1 1 d . .
O8 O 0.84813(5) 0.09008(7) 0.54544(4) 0.01999(14) Uani 1 1 d . .
C1 C 0.74666(7) 0.18964(8) 0.40368(5) 0.01584(16) Uani 1 1 d . .
C2 C 0.68717(6) 0.15109(7) 0.32129(5) 0.01408(15) Uani 1 1 d . .
C3 C 0.58028(7) 0.17990(8) 0.31073(6) 0.01678(16) Uani 1 1 d . .
H3A H 0.5503 0.2193 0.3545 0.020 Uiso 1 1 calc R U
C4 C 0.51732(7) 0.15144(8) 0.23665(6) 0.01774(16) Uani 1 1 d . .
C5 C 0.34185(8) 0.13771(12) 0.16678(8) 0.0324(2) Uani 1 1 d . .
H5A H 0.2692 0.1546 0.1775 0.049 Uiso 1 1 calc R U
H5B H 0.3508 0.0550 0.1621 0.049 Uiso 1 1 calc R U
H5C H 0.3566 0.1744 0.1139 0.049 Uiso 1 1 calc R U
C6 C 0.56061(7) 0.09741(8) 0.17024(6) 0.01732(16) Uani 1 1 d . .
H6A H 0.5184 0.0809 0.1186 0.021 Uiso 1 1 calc R U
C7 C 0.66733(7) 0.06820(7) 0.18150(5) 0.01486(15) Uani 1 1 d . .
C8 C 0.66288(8) -0.00889(8) 0.04066(6) 0.01998(17) Uani 1 1 d . .
H8A H 0.7105 -0.0465 0.0049 0.030 Uiso 1 1 calc R U
H8B H 0.6400 0.0645 0.0154 0.030 Uiso 1 1 calc R U
H8C H 0.6011 -0.0574 0.0451 0.030 Uiso 1 1 calc R U
C9 C 0.73161(6) 0.09262(7) 0.25696(5) 0.01342(15) Uani 1 1 d . .
C10 C 0.84154(7) 0.04268(7) 0.26158(5) 0.01348(15) Uani 1 1 d . .
C11 C 0.92051(6) 0.09916(7) 0.21209(5) 0.01334(15) Uani 1 1 d . .
C12 C 0.97871(7) 0.02657(8) 0.16481(5) 0.01593(16) Uani 1 1 d . .
H12A H 0.9689 -0.0537 0.1662 0.019 Uiso 1 1 calc R U
C13 C 1.05095(7) 0.07437(8) 0.11588(6) 0.01751(16) Uani 1 1 d . .
C14 C 1.10968(10) -0.10791(10) 0.07470(8) 0.0303(2) Uani 1 1 d . .
H14A H 1.1601 -0.1422 0.0397 0.045 Uiso 1 1 calc R U
H14B H 1.0383 -0.1345 0.0552 0.045 Uiso 1 1 calc R U
H14C H 1.1279 -0.1303 0.1339 0.045 Uiso 1 1 calc R U
C15 C 1.06368(7) 0.19273(8) 0.11209(6) 0.01764(16) Uani 1 1 d . .
H15A H 1.1109 0.2249 0.0763 0.021 Uiso 1 1 calc R U
C16 C 1.00672(7) 0.26287(8) 0.16103(5) 0.01530(15) Uani 1 1 d . .
C17 C 1.08668(12) 0.42917(10) 0.10942(10) 0.0403(3) Uani 1 1 d . .
H17A H 1.0871 0.5122 0.1169 0.060 Uiso 1 1 calc R U
H17B H 1.0624 0.4106 0.0504 0.060 Uiso 1 1 calc R U
H17C H 1.1582 0.3993 0.1238 0.060 Uiso 1 1 calc R U
C18 C 0.93425(6) 0.21730(7) 0.21298(5) 0.01308(14) Uani 1 1 d . .
C19 C 0.88828(7) 0.29200(7) 0.27766(5) 0.01461(15) Uani 1 1 d . .
H19A H 0.8102 0.2893 0.2691 0.018 Uiso 1 1 calc R U
H19B H 0.9110 0.3721 0.2718 0.018 Uiso 1 1 calc R U
C20 C 0.92838(7) 0.24640(7) 0.36499(5) 0.01391(15) Uani 1 1 d . .
C21 C 1.03636(7) 0.25851(8) 0.38918(5) 0.01608(16) Uani 1 1 d . .
H21A H 1.0789 0.2983 0.3534 0.019 Uiso 1 1 calc R U
C22 C 1.08237(7) 0.21287(8) 0.46528(6) 0.01614(16) Uani 1 1 d . .
C23 C 1.24236(8) 0.17098(10) 0.55366(7) 0.0258(2) Uani 1 1 d . .
H23A H 1.3185 0.1843 0.5555 0.039 Uiso 1 1 calc R U
H23B H 1.2283 0.0888 0.5508 0.039 Uiso 1 1 calc R U
H23C H 1.2168 0.2025 0.6048 0.039 Uiso 1 1 calc R U
C24 C 1.02126(7) 0.15656(8) 0.52026(5) 0.01589(16) Uani 1 1 d . .
H24A H 1.0527 0.1262 0.5724 0.019 Uiso 1 1 calc R U
C25 C 0.91315(7) 0.14596(7) 0.49676(5) 0.01467(15) Uani 1 1 d . .
C26 C 0.89296(8) 0.04854(9) 0.62664(6) 0.02075(18) Uani 1 1 d . .
H26A H 0.8383 0.0094 0.6546 0.031 Uiso 1 1 calc R U
H26B H 0.9208 0.1128 0.6617 0.031 Uiso 1 1 calc R U
H26C H 0.9503 -0.0049 0.6190 0.031 Uiso 1 1 calc R U
C27 C 0.86461(7) 0.19026(7) 0.41875(5) 0.01398(15) 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
C4 O2 C5 117.64(8)
C7 O3 C8 119.18(7)
C13 O5 C14 116.62(8)
C16 O6 C17 117.54(8)
C22 O7 C23 118.03(7)
C25 O8 C26 117.77(7)
O1 C1 C27 118.71(8)
O1 C1 C2 118.50(8)
C27 C1 C2 122.77(7)
C3 C2 C9 119.85(8)
C3 C2 C1 115.04(7)
C9 C2 C1 125.09(8)
C4 C3 C2 120.60(8)
O2 C4 C3 115.14(8)
O2 C4 C6 124.20(8)
C3 C4 C6 120.65(8)
C4 C6 C7 118.36(8)
O3 C7 C6 123.68(8)
O3 C7 C9 114.34(7)
C6 C7 C9 121.91(8)
C2 C9 C7 118.54(8)
C2 C9 C10 126.88(7)
C7 C9 C10 114.39(7)
O4 C10 C11 121.49(8)
O4 C10 C9 119.58(8)
C11 C10 C9 118.39(7)
C18 C11 C12 122.36(8)
C18 C11 C10 121.61(7)
C12 C11 C10 116.03(7)
C13 C12 C11 118.58(8)
O5 C13 C12 124.63(9)
O5 C13 C15 114.56(8)
C12 C13 C15 120.81(8)
C16 C15 C13 119.51(8)
O6 C16 C15 123.12(8)
O6 C16 C18 115.60(8)
C15 C16 C18 121.28(8)
C11 C18 C16 117.37(8)
C11 C18 C19 121.52(7)
C16 C18 C19 120.30(8)
C18 C19 C20 107.39(7)
C21 C20 C27 119.92(8)
C21 C20 C19 115.99(7)
C27 C20 C19 124.03(7)
C22 C21 C20 120.64(8)
O7 C22 C21 115.37(8)
O7 C22 C24 123.71(8)
C21 C22 C24 120.92(8)
C25 C24 C22 118.48(8)
O8 C25 C24 122.41(8)
O8 C25 C27 115.93(7)
C24 C25 C27 121.63(8)
C20 C27 C25 118.40(8)
C20 C27 C1 122.87(8)
C25 C27 C1 118.13(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2218(11)
O2 C4 1.3664(11)
O2 C5 1.4282(13)
O3 C7 1.3630(10)
O3 C8 1.4294(11)
O4 C10 1.2158(11)
O5 C13 1.3669(11)
O5 C14 1.4293(14)
O6 C16 1.3690(11)
O6 C17 1.4214(13)
O7 C22 1.3616(11)
O7 C23 1.4341(12)
O8 C25 1.3616(10)
O8 C26 1.4378(11)
C1 C27 1.4962(12)
C1 C2 1.5088(12)
C2 C3 1.3958(12)
C2 C9 1.4007(11)
C3 C4 1.3908(13)
C4 C6 1.3950(13)
C6 C7 1.3951(12)
C7 C9 1.4057(12)
C9 C10 1.5128(12)
C10 C11 1.4975(11)
C11 C18 1.3958(12)
C11 C12 1.4002(11)
C12 C13 1.3865(12)
C13 C15 1.3991(13)
C15 C16 1.3897(12)
C16 C18 1.4094(11)
C18 C19 1.5159(11)
C19 C20 1.5223(12)
C20 C21 1.3950(12)
C20 C27 1.4053(12)
C21 C22 1.3920(12)
C22 C24 1.3979(12)
C24 C25 1.3932(12)
C25 C27 1.4218(12)
