#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:26:14 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178469 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/90/4029082.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_4029082
loop_
_publ_author_name
'Griffith, Daniel R.'
'Botta, Lorenzo'
'St Denis, Tyler G.'
'Snyder, Scott A.'
_publ_section_title
;
 Explorations of caffeic acid derivatives: total syntheses of
 rufescenolide, yunnaneic acids C and D, and studies toward yunnaneic
 acids A and B.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              88
_journal_page_last               105
_journal_paper_doi               10.1021/jo4023167
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C47 H54 Cl2 O16'
_chemical_formula_weight         945.80
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 103.590(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.827(4)
_cell_length_b                   18.867(4)
_cell_length_c                   12.772(3)
_cell_measurement_reflns_used    4694
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      26.85
_cell_measurement_theta_min      2.41
_cell_volume                     4643.9(17)
_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      125(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.1234
_diffrn_reflns_av_sigmaI/netI    0.0954
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            31840
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.51
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_T_max  0.9874
_exptl_absorpt_correction_T_min  0.9690
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1992
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.647
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         5768
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.1488
_refine_ls_R_factor_gt           0.0710
_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)+(0.0959P)²+1.8955P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1769
_refine_ls_wR_factor_ref         0.2127
_reflns_number_gt                2977
_reflns_number_total             5768
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4023167_si_006.cif
_cod_data_source_block           dggws10
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'EMPIRICAL'
changed to 'empirical' according to
/usr/data/users/saulius/automatic-downloads/current/ACS/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_cell_volume        4643.8(16)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4029082
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.09754(13) 0.43983(12) 1.11111(19) 0.0333(6) Uani 1 1 d . . .
O2 O 0.09129(14) 0.49148(13) 0.9511(2) 0.0378(6) Uani 1 1 d . . .
O3 O 0.23042(13) 0.06151(13) 0.8938(2) 0.0374(6) Uani 1 1 d . . .
O4 O 0.21712(13) 0.12943(13) 1.03058(19) 0.0352(6) Uani 1 1 d . . .
O5 O 0.00424(10) 0.19459(11) 0.85271(17) 0.0224(5) Uani 1 1 d . . .
O6 O -0.05916(11) 0.08933(11) 0.82185(18) 0.0261(5) Uani 1 1 d . . .
O7 O -0.42272(12) 0.23553(14) 0.9218(2) 0.0366(6) Uani 1 1 d . . .
O8 O -0.33649(13) 0.33462(13) 0.9132(2) 0.0386(7) Uani 1 1 d . . .
C1 C 0.0909(2) 0.5085(2) 1.1575(3) 0.0435(10) Uani 1 1 d . . .
H1A H 0.0951 0.5034 1.2352 0.065 Uiso 1 1 calc R . .
H1B H 0.0455 0.5288 1.1238 0.065 Uiso 1 1 calc R . .
H1C H 0.1277 0.5399 1.1451 0.065 Uiso 1 1 calc R . .
C2 C 0.09856(17) 0.43911(18) 1.0067(3) 0.0265(7) Uani 1 1 d . . .
C3 C 0.10923(16) 0.36659(18) 0.9722(3) 0.0245(7) Uani 1 1 d . . .
H3A H 0.1196 0.3296 1.0240 0.029 Uiso 1 1 calc R . .
C4 C 0.10432(16) 0.35239(17) 0.8678(3) 0.0248(7) Uani 1 1 d . . .
H4A H 0.0934 0.3916 0.8202 0.030 Uiso 1 1 calc R . .
C5 C 0.11338(16) 0.28560(17) 0.8183(3) 0.0222(7) Uani 1 1 d . . .
C6 C 0.12501(16) 0.21517(17) 0.8784(3) 0.0222(7) Uani 1 1 d . . .
H6A H 0.1275 0.2219 0.9569 0.027 Uiso 1 1 calc R . .
C7 C 0.19349(16) 0.18390(17) 0.8603(3) 0.0228(7) Uani 1 1 d . . .
H7A H 0.2307 0.2203 0.8834 0.027 Uiso 1 1 calc R . .
C8 C 0.21546(16) 0.11758(19) 0.9268(3) 0.0260(7) Uani 1 1 d . . .
C9 C 0.2355(2) 0.0693(2) 1.1020(3) 0.0442(10) Uani 1 1 d . . .
H9A H 0.2455 0.0856 1.1769 0.066 Uiso 1 1 calc R . .
H9B H 0.2766 0.0460 1.0880 0.066 Uiso 1 1 calc R . .
H9C H 0.1968 0.0357 1.0894 0.066 Uiso 1 1 calc R . .
C10 C 0.06526(16) 0.16568(17) 0.8270(3) 0.0220(7) Uani 1 1 d . . .
H10A H 0.0744 0.1172 0.8590 0.026 Uiso 1 1 calc R . .
C11 C -0.05809(16) 0.16178(16) 0.7965(2) 0.0213(7) Uani 1 1 d . . .
C12 C -0.0577(2) 0.0740(2) 0.9314(3) 0.0374(9) Uani 1 1 d . . .
H12A H -0.0534 0.0227 0.9432 0.056 Uiso 1 1 calc R . .
H12B H -0.1007 0.0907 0.9483 0.056 Uiso 1 1 calc R . .
H12C H -0.0180 0.0980 0.9782 0.056 Uiso 1 1 calc R . .
C13 C -0.11021(16) 0.27849(17) 0.7863(3) 0.0232(7) Uani 1 1 d . . .
H13A H -0.1036 0.3180 0.8338 0.028 Uiso 1 1 calc R . .
C14 C -0.11763(16) 0.20479(16) 0.8252(2) 0.0211(7) Uani 1 1 d . . .
H14A H -0.1145 0.2040 0.9045 0.025 Uiso 1 1 calc R . .
C15 C -0.18576(16) 0.16960(17) 0.7618(2) 0.0221(7) Uani 1 1 d . . .
H15A H -0.1788 0.1173 0.7719 0.027 Uiso 1 1 calc R . .
C16 C -0.24934(16) 0.18779(18) 0.8029(3) 0.0239(7) Uani 1 1 d . . .
C17 C -0.29676(18) 0.13515(19) 0.8083(3) 0.0313(8) Uani 1 1 d . . .
H17A H -0.2890 0.0886 0.7851 0.038 Uiso 1 1 calc R . .
C18 C -0.35569(18) 0.1484(2) 0.8469(3) 0.0341(9) Uani 1 1 d . . .
H18A H -0.3876 0.1114 0.8498 0.041 Uiso 1 1 calc R . .
C19 C -0.36743(16) 0.2156(2) 0.8808(3) 0.0289(8) Uani 1 1 d . . .
C20 C -0.31970(17) 0.27034(18) 0.8759(3) 0.0275(7) Uani 1 1 d . . .
C21 C -0.26214(17) 0.25597(18) 0.8373(3) 0.0279(8) Uani 1 1 d . . .
H21A H -0.2303 0.2930 0.8337 0.033 Uiso 1 1 calc R . .
C22 C -0.4737(2) 0.1825(2) 0.9258(4) 0.0448(10) Uani 1 1 d . . .
H22A H -0.5077 0.2016 0.9629 0.067 Uiso 1 1 calc R . .
H22B H -0.4510 0.1410 0.9649 0.067 Uiso 1 1 calc R . .
H22C H -0.4973 0.1687 0.8523 0.067 Uiso 1 1 calc R . .
C23 C -0.2912(2) 0.3921(2) 0.9070(4) 0.0468(11) Uani 1 1 d . . .
H23A H -0.3087 0.4353 0.9340 0.070 Uiso 1 1 calc R . .
H23B H -0.2889 0.3992 0.8319 0.070 Uiso 1 1 calc R . .
H23C H -0.2447 0.3815 0.9508 0.070 Uiso 1 1 calc R . .
C24 C 0.0183(4) 0.1444(4) 0.2236(7) 0.046(2) Uani 0.50 1 d P A -1
H24A H 0.0341 0.1701 0.2926 0.056 Uiso 0.50 1 calc PR A -1
H24B H -0.0246 0.1676 0.1826 0.056 Uiso 0.50 1 calc PR A -1
Cl1 Cl 0.0000 0.05677(9) 0.2500 0.0696(5) Uani 1 2 d S . .
Cl2 Cl 0.08326(11) 0.15058(14) 0.14882(18) 0.0568(6) Uani 0.50 1 d P A -1
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'
Cl Cl 0.1484 0.1585 '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
C2 O1 C1 116.2(3) . .
C8 O4 C9 116.0(3) . .
C11 O5 C10 113.6(2) . .
C11 O6 C12 115.3(3) . .
C19 O7 C22 117.1(3) . .
C20 O8 C23 116.5(3) . .
O2 C2 O1 123.4(3) . .
O2 C2 C3 126.3(3) . .
O1 C2 C3 110.2(3) . .
C4 C3 C2 120.2(3) . .
C3 C4 C5 128.6(3) . .
C13 C5 C4 123.3(3) 2_556 .
C13 C5 C6 112.6(3) 2_556 .
C4 C5 C6 124.1(3) . .
C5 C6 C10 107.8(2) . .
C5 C6 C7 106.9(3) . .
C10 C6 C7 108.8(3) . .
C8 C7 C6 112.2(3) . .
C8 C7 C15 111.4(3) . 2_556
C6 C7 C15 109.5(2) . 2_556
O3 C8 O4 123.0(3) . .
O3 C8 C7 126.3(3) . .
O4 C8 C7 110.7(3) . .
O5 C10 C6 106.2(2) . .
O5 C10 C11 111.7(2) . 2_556
C6 C10 C11 110.0(2) . 2_556
O6 C11 O5 111.5(2) . .
O6 C11 C14 113.7(2) . .
O5 C11 C14 105.9(2) . .
O6 C11 C10 106.1(2) . 2_556
O5 C11 C10 110.8(2) . 2_556
C14 C11 C10 108.9(2) . 2_556
C5 C13 C14 116.2(3) 2_556 .
C13 C14 C11 105.6(2) . .
C13 C14 C15 111.5(3) . .
C11 C14 C15 105.7(2) . .
C16 C15 C14 114.6(3) . .
C16 C15 C7 114.5(3) . 2_556
C14 C15 C7 108.5(2) . 2_556
C17 C16 C21 118.0(3) . .
C17 C16 C15 119.1(3) . .
C21 C16 C15 122.9(3) . .
C16 C17 C18 121.7(3) . .
C19 C18 C17 119.7(3) . .
O7 C19 C18 125.6(3) . .
O7 C19 C20 114.8(3) . .
C18 C19 C20 119.7(3) . .
O8 C20 C21 126.1(3) . .
O8 C20 C19 114.3(3) . .
C21 C20 C19 119.6(3) . .
C20 C21 C16 121.4(3) . .
Cl1 C24 Cl2 112.1(4) . .
C24 Cl1 C24 36.9(5) . 2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C2 1.338(4) .
O1 C1 1.444(4) .
O2 C2 1.206(4) .
O3 C8 1.202(4) .
O4 C8 1.337(4) .
O4 C9 1.447(4) .
O5 C11 1.417(4) .
O5 C10 1.434(4) .
O6 C11 1.406(4) .
O6 C12 1.423(4) .
O7 C19 1.374(4) .
O7 C22 1.431(4) .
O8 C20 1.372(4) .
O8 C23 1.422(5) .
C2 C3 1.468(5) .
C3 C4 1.340(5) .
C4 C5 1.440(5) .
C5 C13 1.330(5) 2_556
C5 C6 1.525(4) .
C6 C10 1.530(4) .
C6 C7 1.547(4) .
C7 C8 1.517(5) .
C7 C15 1.554(4) 2_556
C10 C11 1.552(4) 2_556
C11 C14 1.546(4) .
C11 C10 1.552(4) 2_556
C13 C5 1.330(5) 2_556
C13 C14 1.495(4) .
C14 C15 1.551(4) .
C15 C16 1.515(4) .
C15 C7 1.554(4) 2_556
C16 C17 1.380(5) .
C16 C21 1.402(5) .
C17 C18 1.393(5) .
C18 C19 1.376(5) .
C19 C20 1.413(5) .
C20 C21 1.373(5) .
C24 Cl1 1.743(8) .
C24 Cl2 1.778(8) .
Cl1 C24 1.744(8) 2
