#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:26:14 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178469 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/90/4029080.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_4029080
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            'C22 H22 O8'
_chemical_formula_weight         414.40
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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                 100.866(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3052(10)
_cell_length_b                   14.2683(18)
_cell_length_c                   17.062(2)
_cell_measurement_reflns_used    3825
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      21.97
_cell_measurement_theta_min      2.43
_cell_volume                     1985.6(4)
_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      130(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  0.1057
_diffrn_reflns_av_sigmaI/netI    0.0880
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            27255
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.9853
_exptl_absorpt_correction_T_min  0.9719
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4925
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.1398
_refine_ls_R_factor_gt           0.0553
_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)+(0.0350P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.1190
_reflns_number_gt                2377
_reflns_number_total             4925
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4023167_si_001.cif
_cod_data_source_block           dangs10
_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.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4029080
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
O1 O 0.6314(2) 0.10538(11) 0.10682(10) 0.0493(5) Uani 1 1 d .
O2 O 0.57524(18) 0.28684(10) 0.05513(9) 0.0411(4) Uani 1 1 d .
O3 O 0.42016(18) 0.18937(11) -0.03909(10) 0.0439(4) Uani 1 1 d .
O4 O 0.3077(2) 0.13277(12) -0.15888(11) 0.0570(5) Uani 1 1 d .
O5 O 1.1712(2) 0.46880(11) -0.06178(10) 0.0465(4) Uani 1 1 d .
O6 O 0.96390(19) 0.53821(11) -0.14300(9) 0.0465(4) Uani 1 1 d .
O7 O 1.03738(19) -0.16012(11) -0.27003(9) 0.0461(4) Uani 1 1 d .
O8 O 0.7798(2) -0.22767(11) -0.22539(10) 0.0542(5) Uani 1 1 d .
C1 C 0.6653(3) 0.13152(15) 0.04522(15) 0.0384(6) Uani 1 1 d .
C2 C 0.5861(3) 0.21827(15) 0.00001(14) 0.0365(6) Uani 1 1 d .
C3 C 0.4288(3) 0.15566(16) -0.11349(16) 0.0449(6) Uani 1 1 d .
C4 C 0.6053(3) 0.15415(15) -0.12210(13) 0.0383(6) Uani 1 1 d .
H4A H 0.6187 0.1621 -0.1788 0.046 Uiso 1 1 calc R
C5 C 0.6734(3) 0.23846(15) -0.06912(13) 0.0360(6) Uani 1 1 d .
H5A H 0.6367 0.2994 -0.0956 0.043 Uiso 1 1 calc R
C6\ C 0.6834(3) 0.06110(16) -0.08442(14) 0.0424(6) Uani 1 1 d .
H6\A H 0.5907 0.0195 -0.0769 0.051 Uiso 1 1 calc R
C7 C 0.7820(3) 0.08375(16) 0.00036(14) 0.0402(6) Uani 1 1 d .
H7A H 0.8308 0.0260 0.0285 0.048 Uiso 1 1 calc R
C8 C 0.9099(3) 0.15651(15) -0.00460(13) 0.0380(6) Uani 1 1 d .
H8A H 1.0228 0.1464 0.0166 0.046 Uiso 1 1 calc R
C9 C 0.8550(3) 0.23645(15) -0.04077(13) 0.0345(5) Uani 1 1 d .
C10 C 0.9588(3) 0.31516(15) -0.05193(13) 0.0366(6) Uani 1 1 d .
H10A H 1.0720 0.3095 -0.0292 0.044 Uiso 1 1 calc R
C11 C 0.9125(3) 0.39427(15) -0.09047(13) 0.0359(6) Uani 1 1 d .
H11A H 0.8009 0.4025 -0.1151 0.043 Uiso 1 1 calc R
C12 C 1.0300(3) 0.46861(16) -0.09556(13) 0.0349(5) Uani 1 1 d .
C13 C 1.0731(3) 0.61362(17) -0.15344(15) 0.0511(7) Uani 1 1 d .
H13A H 1.0100 0.6653 -0.1819 0.077 Uiso 1 1 calc R
H13B H 1.1536 0.5913 -0.1844 0.077 Uiso 1 1 calc R
H13C H 1.1302 0.6355 -0.1011 0.077 Uiso 1 1 calc R
C14 C 0.5105(3) 0.37507(16) 0.02403(15) 0.0479(7) Uani 1 1 d .
H14A H 0.4876 0.4143 0.0678 0.072 Uiso 1 1 calc R
H14B H 0.4088 0.3647 -0.0147 0.072 Uiso 1 1 calc R
H14C H 0.5907 0.4066 -0.0023 0.072 Uiso 1 1 calc R
C15 C 0.7822(3) 0.00739(16) -0.13551(14) 0.0412(6) Uani 1 1 d .
C16 C 0.9168(3) 0.04289(18) -0.16164(15) 0.0549(7) Uani 1 1 d .
H16A H 0.9503 0.1055 -0.1486 0.066 Uiso 1 1 calc R
C17 C 1.0045(3) -0.01091(18) -0.20664(15) 0.0507(7) Uani 1 1 d .
H17A H 1.0971 0.0152 -0.2239 0.061 Uiso 1 1 calc R
C18 C 0.9587(3) -0.10135(17) -0.22638(13) 0.0395(6) Uani 1 1 d .
C19 C 0.8199(3) -0.13790(16) -0.20189(13) 0.0392(6) Uani 1 1 d .
C20 C 0.7342(3) -0.08395(16) -0.15695(13) 0.0390(6) Uani 1 1 d .
H20A H 0.6406 -0.1095 -0.1402 0.047 Uiso 1 1 calc R
C21 C 1.1790(3) -0.1236(2) -0.29551(15) 0.0593(8) Uani 1 1 d .
H21A H 1.2296 -0.1729 -0.3227 0.089 Uiso 1 1 calc R
H21B H 1.2578 -0.1016 -0.2490 0.089 Uiso 1 1 calc R
H21C H 1.1470 -0.0712 -0.3323 0.089 Uiso 1 1 calc R
C22 C 0.6547(4) -0.27067(19) -0.1901(2) 0.0887(12) Uani 1 1 d .
H22A H 0.6536 -0.3383 -0.2001 0.133 Uiso 1 1 calc R
H22B H 0.5479 -0.2440 -0.2137 0.133 Uiso 1 1 calc R
H22C H 0.6772 -0.2591 -0.1325 0.133 Uiso 1 1 calc R
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
C2 O2 C14 116.22(17)
C3 O3 C2 108.03(18)
C12 O6 C13 115.79(19)
C18 O7 C21 116.62(18)
C19 O8 C22 115.77(18)
O1 C1 C7 125.8(2)
O1 C1 C2 122.8(2)
C7 C1 C2 111.4(2)
O2 C2 O3 109.48(17)
O2 C2 C5 119.87(18)
O3 C2 C5 104.10(17)
O2 C2 C1 107.89(18)
O3 C2 C1 106.08(17)
C5 C2 C1 108.61(19)
O4 C3 O3 120.8(2)
O4 C3 C4 130.7(2)
O3 C3 C4 108.6(2)
C3 C4 C5 100.82(18)
C3 C4 C6\ 108.02(19)
C5 C4 C6\ 110.06(18)
C9 C5 C2 110.13(18)
C9 C5 C4 114.18(18)
C2 C5 C4 97.51(17)
C15 C6\ C7 113.17(19)
C15 C6\ C4 114.93(19)
C7 C6\ C4 108.12(18)
C8 C7 C1 104.24(18)
C8 C7 C6\ 110.22(18)
C1 C7 C6\ 106.87(19)
C9 C8 C7 115.7(2)
C8 C9 C10 124.2(2)
C8 C9 C5 113.7(2)
C10 C9 C5 122.1(2)
C11 C10 C9 126.9(2)
C10 C11 C12 121.0(2)
O5 C12 O6 122.8(2)
O5 C12 C11 125.2(2)
O6 C12 C11 112.0(2)
C16 C15 C20 118.0(2)
C16 C15 C6\ 124.2(2)
C20 C15 C6\ 117.8(2)
C15 C16 C17 121.3(2)
C18 C17 C16 120.5(2)
O7 C18 C17 125.0(2)
O7 C18 C19 116.1(2)
C17 C18 C19 119.0(2)
O8 C19 C20 124.5(2)
O8 C19 C18 115.6(2)
C20 C19 C18 120.0(2)
C19 C20 C15 121.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.198(2)
O2 C2 1.372(3)
O2 C14 1.431(3)
O3 C3 1.372(3)
O3 C2 1.472(3)
O4 C3 1.194(3)
O5 C12 1.205(2)
O6 C12 1.332(3)
O6 C13 1.440(3)
O7 C18 1.367(3)
O7 C21 1.428(3)
O8 C19 1.364(3)
O8 C22 1.433(3)
C1 C7 1.506(3)
C1 C2 1.539(3)
C2 C5 1.524(3)
C3 C4 1.501(3)
C4 C5 1.546(3)
C4 C6\ 1.562(3)
C5 C9 1.495(3)
C6\ C15 1.513(3)
C6\ C7 1.556(3)
C7 C8 1.499(3)
C8 C9 1.336(3)
C9 C10 1.450(3)
C10 C11 1.326(3)
C11 C12 1.455(3)
C15 C16 1.376(3)
C15 C20 1.391(3)
C16 C17 1.385(3)
C17 C18 1.369(3)
C18 C19 1.399(3)
C19 C20 1.376(3)
