#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:52:40 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180199 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/95/7109551.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_7109551
loop_
_publ_author_name
'Shuang Liang'
'Shan-Xiang Liu'
'Hui-Zi Jin'
'Lei Shan'
'Shi-Chong Yu'
'Yun-Heng Shen'
'Hui-Liang Li'
'Qiu-Ye Wu'
'Qing-Yan Sun'
'Wei-Dong Zhang'
_publ_section_title
;
 Two novel innovanoside dimers from Daphne aurantiaca and a concise total
 synthesis of diinnovanoside A
;
_journal_name_full               Chem.Commun.
_journal_page_first              6968
_journal_paper_doi               10.1039/c3cc41811a
_journal_volume                  49
_journal_year                    2013
_chemical_formula_sum            'C24 H24 O8'
_chemical_formula_weight         440.43
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 111.2380(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   14.0632(14)
_cell_length_b                   7.2591(7)
_cell_length_c                   11.4968(11)
_cell_measurement_reflns_used    5496
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      30.55
_cell_measurement_theta_min      3.11
_cell_volume                     1093.95(18)
_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      140(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0178
_diffrn_reflns_av_sigmaI/netI    0.0200
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10346
_diffrn_reflns_theta_full        30.67
_diffrn_reflns_theta_max         30.67
_diffrn_reflns_theta_min         3.11
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.9860
_exptl_absorpt_correction_T_min  0.9704
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         3382
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0656P)²+0.3300P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1169
_reflns_number_gt                2945
_reflns_number_total             3382
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc41811a.txt
_cod_data_source_block           dm12579
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7109551
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.40571(7) 1.16170(14) 0.70447(9) 0.0386(2) Uani 1 1 d .
O2 O 0.37061(6) 1.03144(11) 0.51547(7) 0.02812(18) Uani 1 1 d .
O3 O -0.15609(5) 0.62160(10) 0.63690(7) 0.02269(16) Uani 1 1 d .
O4 O -0.01918(6) 0.45178(11) 0.74756(7) 0.02435(16) Uani 1 1 d .
C1 C 0.07922(6) 0.52547(12) 0.56733(8) 0.01617(16) Uani 1 1 d .
H1 H 0.1083 0.4460 0.6431 0.019 Uiso 1 1 calc R
C2 C -0.02810(6) 0.59662(12) 0.55398(8) 0.01601(17) Uani 1 1 d .
H2 H -0.0358 0.7312 0.5344 0.019 Uiso 1 1 calc R
C5 C 0.15643(6) 0.66468(12) 0.56090(8) 0.01686(17) Uani 1 1 d .
C6 C 0.12643(7) 0.81903(13) 0.48330(9) 0.01962(18) Uani 1 1 d .
H6 H 0.0559 0.8404 0.4386 0.024 Uiso 1 1 calc R
C7 C 0.19783(7) 0.94176(14) 0.47037(9) 0.02156(19) Uani 1 1 d .
H7 H 0.1767 1.0460 0.4173 0.026 Uiso 1 1 calc R
C8 C 0.30021(7) 0.90932(14) 0.53623(9) 0.02202(19) Uani 1 1 d .
C9 C 0.33327(7) 0.75750(15) 0.61304(9) 0.0243(2) Uani 1 1 d .
H9 H 0.4040 0.7367 0.6567 0.029 Uiso 1 1 calc R
C10 C 0.26084(7) 0.63551(14) 0.62525(9) 0.02126(19) Uani 1 1 d .
H10 H 0.2827 0.5310 0.6780 0.026 Uiso 1 1 calc R
C11 C 0.48016(10) 1.28721(18) 0.56311(13) 0.0372(3) Uani 1 1 d .
H11A H 0.4932 1.3996 0.6137 0.056 Uiso 1 1 calc R
H11B H 0.4440 1.3187 0.4752 0.056 Uiso 1 1 calc R
H11C H 0.5452 1.2279 0.5727 0.056 Uiso 1 1 calc R
C12 C 0.41631(7) 1.15803(15) 0.60551(10) 0.0248(2) Uani 1 1 d .
C13 C -0.06366(7) 0.54800(13) 0.65889(8) 0.01772(17) Uani 1 1 d .
C14 C -0.20546(9) 0.56977(18) 0.72249(12) 0.0337(3) Uani 1 1 d .
H14A H -0.2201 0.4374 0.7150 0.051 Uiso 1 1 calc R
H14B H -0.2694 0.6386 0.7024 0.051 Uiso 1 1 calc R
H14C H -0.1604 0.5982 0.8081 0.051 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C12 O2 C8 117.57(8) . .
C13 O3 C14 116.09(8) . .
C5 C1 C2 117.76(7) . .
C5 C1 C2 115.90(7) . 3_566
C2 C1 C2 89.09(6) . 3_566
C5 C1 H1 110.8 . .
C2 C1 H1 110.8 . .
C2 C1 H1 110.8 3_566 .
C13 C2 C1 115.90(7) . .
C13 C2 C1 113.38(7) . 3_566
C1 C2 C1 90.91(6) . 3_566
C13 C2 H2 111.7 . .
C1 C2 H2 111.7 . .
C1 C2 H2 111.7 3_566 .
C6 C5 C10 118.32(8) . .
C6 C5 C1 120.87(8) . .
C10 C5 C1 120.64(8) . .
C7 C6 C5 121.26(8) . .
C7 C6 H6 119.4 . .
C5 C6 H6 119.4 . .
C8 C7 C6 118.78(9) . .
C8 C7 H7 120.6 . .
C6 C7 H7 120.6 . .
C7 C8 C9 121.86(9) . .
C7 C8 O2 117.08(9) . .
C9 C8 O2 120.93(9) . .
C8 C9 C10 118.77(9) . .
C8 C9 H9 120.6 . .
C10 C9 H9 120.6 . .
C9 C10 C5 121.00(9) . .
C9 C10 H10 119.5 . .
C5 C10 H10 119.5 . .
C12 C11 H11A 109.5 . .
C12 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C12 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
O1 C12 O2 123.38(9) . .
O1 C12 C11 126.16(10) . .
O2 C12 C11 110.46(9) . .
O4 C13 O3 124.04(8) . .
O4 C13 C2 126.27(8) . .
O3 C13 C2 109.63(8) . .
O3 C14 H14A 109.5 . .
O3 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
O3 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C12 1.2002(14) .
O2 C12 1.3590(13) .
O2 C8 1.4122(11) .
O3 C13 1.3420(11) .
O3 C14 1.4446(12) .
O4 C13 1.2068(12) .
C1 C5 1.5046(12) .
C1 C2 1.5494(12) .
C1 C2 1.5877(12) 3_566
C1 H1 1.0000 .
C2 C13 1.5054(12) .
C2 C1 1.5878(12) 3_566
C2 H2 1.0000 .
C5 C6 1.3987(12) .
C5 C10 1.4004(12) .
C6 C7 1.3900(12) .
C6 H6 0.9500 .
C7 C8 1.3827(14) .
C7 H7 0.9500 .
C8 C9 1.3831(15) .
C9 C10 1.3947(13) .
C9 H9 0.9500 .
C10 H10 0.9500 .
C11 C12 1.4968(14) .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C5 C1 C2 C13 -124.29(8) . .
C2 C1 C2 C13 116.67(9) 3_566 .
C5 C1 C2 C1 119.04(9) . 3_566
C2 C1 C2 C1 0.0 3_566 3_566
C2 C1 C5 C6 -34.36(12) . .
C2 C1 C5 C6 69.28(11) 3_566 .
C2 C1 C5 C10 150.51(9) . .
C2 C1 C5 C10 -105.86(10) 3_566 .
C10 C5 C6 C7 -0.39(14) . .
C1 C5 C6 C7 -175.63(9) . .
C5 C6 C7 C8 -0.17(15) . .
C6 C7 C8 C9 0.81(15) . .
C6 C7 C8 O2 176.67(8) . .
C12 O2 C8 C7 104.87(11) . .
C12 O2 C8 C9 -79.23(13) . .
C7 C8 C9 C10 -0.85(16) . .
O2 C8 C9 C10 -176.56(9) . .
C8 C9 C10 C5 0.27(15) . .
C6 C5 C10 C9 0.33(14) . .
C1 C5 C10 C9 175.59(9) . .
C8 O2 C12 O1 5.84(16) . .
C8 O2 C12 C11 -174.40(10) . .
C14 O3 C13 O4 -3.99(14) . .
C14 O3 C13 C2 173.31(9) . .
C1 C2 C13 O4 -4.28(13) . .
C1 C2 C13 O4 98.97(11) 3_566 .
C1 C2 C13 O3 178.50(7) . .
C1 C2 C13 O3 -78.25(9) 3_566 .
