#------------------------------------------------------------------------------
#$Date: 2018-01-06 03:57:01 +0200 (Sat, 06 Jan 2018) $
#$Revision: 204800 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/32/4033228.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_4033228
loop_
_publ_author_name
'Liu, Lu'
'Xu, Guan-Ling'
'Ma, Xiao-Xia'
'Khan, Afsar'
'Tan, Wen-Hong'
'Yang, Zhu-Ya'
'Zhou, Zhi-Hong'
_publ_section_title
;
 Sweritranslactones A-C: Unusual Skeleton Secoiridoid Dimers via
 [4 + 2] Cycloaddition from Swertiamarin.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13263
_journal_page_last               13267
_journal_paper_doi               10.1021/acs.joc.7b02383
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C19 H18 O6'
_chemical_formula_sum            'C19 H18 O6'
_chemical_formula_weight         342.33
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 89.933(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.722(3)
_cell_length_b                   12.395(5)
_cell_length_c                   15.776(6)
_cell_measurement_reflns_used    3139
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.74
_cell_measurement_theta_min      2.58
_cell_volume                     1510.0(10)
_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-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.980
_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  0.1158
_diffrn_reflns_av_unetI/netI     0.1120
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12895
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.153
_diffrn_reflns_theta_min         2.090
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.660
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.260
_exptl_transmission_factor_max   0.7457
_exptl_transmission_factor_min   0.5517
_refine_diff_density_max         2.101
_refine_diff_density_min         -0.633
_refine_diff_density_rms         0.234
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3632
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      2.114
_refine_ls_R_factor_all          0.3180
_refine_ls_R_factor_gt           0.2296
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.5580
_refine_ls_wR_factor_ref         0.5955
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1944
_reflns_number_total             3632
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo7b02383_si_003.cif
_cod_data_source_block           mo_sww5_0m
_cod_depositor_comments
'Adding full bibliography for 4033228--4033230.cif.'
_cod_database_code               4033228
_shelx_shelxl_version_number     2014/7
_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   0.929
_shelx_estimated_absorpt_t_max   0.971
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
O7 O 0.5066(9) 0.8134(6) 0.0103(4) 0.0424(19) Uani 1 1 d . .
C4 C 0.8221(12) 0.5580(7) 0.0758(6) 0.030(2) Uani 1 1 d . .
H4A H 0.9390 0.5658 0.1008 0.036 Uiso 1 1 calc R U
H4B H 0.8363 0.5350 0.0161 0.036 Uiso 1 1 calc R U
C20 C 0.9669(12) 0.7578(7) 0.0062(6) 0.031(2) Uani 1 1 d . .
H20 H 1.0250 0.6903 0.0037 0.037 Uiso 1 1 calc R U
O15 O 0.3868(13) 0.5293(7) 0.3165(5) 0.062(2) Uani 1 1 d . .
O1 O 0.2971(11) 0.5506(7) 0.0990(5) 0.053(2) Uani 1 1 d . .
C21 C 1.0556(13) 0.8415(9) -0.0267(6) 0.036(2) Uani 1 1 d . .
H21A H 1.0062 0.9117 -0.0265 0.043 Uiso 1 1 calc R U
H21B H 1.1676 0.8303 -0.0501 0.043 Uiso 1 1 calc R U
C6 C 0.7975(13) 0.7546(8) 0.0448(6) 0.035(2) Uani 1 1 d . .
C11 C 0.2972(12) 0.7783(7) 0.2164(5) 0.027(2) Uani 1 1 d . .
C19 C 0.4305(11) 0.7575(8) 0.0715(5) 0.029(2) Uani 1 1 d . .
H19 H 0.3202 0.7263 0.0491 0.035 Uiso 1 1 calc R U
O9 O 0.6460(8) 0.7902(5) 0.2182(4) 0.0321(16) Uani 1 1 d . .
C5 C 0.7326(12) 0.6637(7) 0.0781(5) 0.030(2) Uani 1 1 d . .
C1 C 0.4515(14) 0.5589(8) 0.1049(5) 0.036(2) Uani 1 1 d . .
C17 C 0.5615(14) 0.6908(8) 0.2127(6) 0.038(2) Uani 1 1 d . .
H17 H 0.6309 0.6331 0.2410 0.046 Uiso 1 1 calc R U
O14 O 0.1523(12) 0.6289(7) 0.3311(6) 0.066(3) Uani 1 1 d . .
C16 C 0.3858(14) 0.6967(8) 0.2496(6) 0.039(2) Uani 1 1 d . .
C18 C 0.5384(16) 0.6649(8) 0.1137(6) 0.044(3) Uani 1 1 d . .
C15 C 0.3122(16) 0.6159(11) 0.3023(6) 0.048(3) Uani 1 1 d . .
C7 C 0.6772(13) 0.8507(9) 0.0309(7) 0.040(3) Uani 1 1 d . .
H7 H 0.7221 0.8933 -0.0182 0.048 Uiso 1 1 calc R U
C10 C 0.3850(16) 0.8372(9) 0.1495(7) 0.052(3) Uani 1 1 d . .
H10 H 0.3117 0.8986 0.1295 0.062 Uiso 1 1 calc R U
C8 C 0.6612(14) 0.9228(9) 0.1030(9) 0.055(3) Uani 1 1 d . .
H8A H 0.6067 0.9907 0.0835 0.066 Uiso 1 1 calc R U
H8B H 0.7789 0.9408 0.1234 0.066 Uiso 1 1 calc R U
C9 C 0.5511(16) 0.8770(9) 0.1813(6) 0.050(3) Uani 1 1 d . .
H9 H 0.5318 0.9352 0.2242 0.060 Uiso 1 1 calc R U
C3 C 0.7227(14) 0.4715(8) 0.1241(7) 0.044(3) Uani 1 1 d . .
H3A H 0.7767 0.4006 0.1125 0.052 Uiso 1 1 calc R U
H3B H 0.7339 0.4857 0.1856 0.052 Uiso 1 1 calc R U
C12 C 0.1047(17) 0.7899(11) 0.2431(8) 0.058(4) Uani 1 1 d . .
H12A H 0.0732 0.8672 0.2469 0.070 Uiso 1 1 calc R U
H12B H 0.0290 0.7554 0.2004 0.070 Uiso 1 1 calc R U
C13 C 0.0814(17) 0.7386(9) 0.3244(9) 0.064(4) Uani 1 1 d . .
H13A H -0.0441 0.7357 0.3371 0.076 Uiso 1 1 calc R U
H13B H 0.1364 0.7841 0.3683 0.076 Uiso 1 1 calc R U
O2 O 0.5450(11) 0.4656(6) 0.1035(4) 0.050(2) 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
C19 O7 C7 114.1(7)
C5 C4 C3 112.0(8)
C5 C4 H4A 109.2
C3 C4 H4A 109.2
C5 C4 H4B 109.2
C3 C4 H4B 109.2
H4A C4 H4B 107.9
C21 C20 C6 130.1(9)
C21 C20 H20 114.9
C6 C20 H20 114.9
C20 C21 H21A 120.0
C20 C21 H21B 120.0
H21A C21 H21B 120.0
C5 C6 C20 121.8(8)
C5 C6 C7 119.0(9)
C20 C6 C7 118.0(8)
C16 C11 C10 115.4(9)
C16 C11 C12 117.2(9)
C10 C11 C12 126.7(10)
O7 C19 C18 117.2(8)
O7 C19 C10 109.3(8)
C18 C19 C10 103.9(7)
O7 C19 H19 108.7
C18 C19 H19 108.7
C10 C19 H19 108.7
C17 O9 C9 113.5(8)
C6 C5 C4 124.0(8)
C6 C5 C18 118.6(8)
C4 C5 C18 117.0(7)
O1 C1 O2 116.9(10)
O1 C1 C18 122.2(10)
O2 C1 C18 120.9(10)
O9 C17 C16 111.1(8)
O9 C17 C18 106.8(7)
C16 C17 C18 106.9(9)
O9 C17 H17 110.6
C16 C17 H17 110.6
C18 C17 H17 110.6
C15 O14 C13 115.8(9)
C11 C16 C15 124.2(10)
C11 C16 C17 110.8(9)
C15 C16 C17 124.2(10)
C1 C18 C19 111.7(9)
C1 C18 C5 112.5(8)
C19 C18 C5 110.9(7)
C1 C18 C17 108.6(7)
C19 C18 C17 109.0(8)
C5 C18 C17 103.8(9)
O15 C15 O14 118.5(11)
O15 C15 C16 122.1(11)
O14 C15 C16 119.1(12)
O7 C7 C8 107.4(9)
O7 C7 C6 109.9(8)
C8 C7 C6 114.8(9)
O7 C7 H7 108.2
C8 C7 H7 108.2
C6 C7 H7 108.2
C11 C10 C9 109.2(10)
C11 C10 C19 110.3(9)
C9 C10 C19 106.1(8)
C11 C10 H10 110.4
C9 C10 H10 110.4
C19 C10 H10 110.4
C7 C8 C9 115.5(9)
C7 C8 H8A 108.4
C9 C8 H8A 108.4
C7 C8 H8B 108.4
C9 C8 H8B 108.4
H8A C8 H8B 107.5
O9 C9 C10 109.7(10)
O9 C9 C8 108.0(9)
C10 C9 C8 108.6(9)
O9 C9 H9 110.2
C10 C9 H9 110.2
C8 C9 H9 110.2
O2 C3 C4 114.3(8)
O2 C3 H3A 108.7
C4 C3 H3A 108.7
O2 C3 H3B 108.7
C4 C3 H3B 108.7
H3A C3 H3B 107.6
C13 C12 C11 108.6(11)
C13 C12 H12A 110.0
C11 C12 H12A 110.0
C13 C12 H12B 110.0
C11 C12 H12B 110.0
H12A C12 H12B 108.3
C12 C13 O14 115.2(9)
C12 C13 H13A 108.5
O14 C13 H13A 108.5
C12 C13 H13B 108.5
O14 C13 H13B 108.5
H13A C13 H13B 107.5
C1 O2 C3 117.8(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O7 C19 1.326(12)
O7 C7 1.434(12)
C4 C5 1.482(12)
C4 C3 1.522(12)
C4 H4A 0.9900
C4 H4B 0.9900
C20 C21 1.348(12)
C20 C6 1.442(13)
C20 H20 0.9500
O15 C15 1.239(15)
O1 C1 1.200(12)
C21 H21A 0.9500
C21 H21B 0.9500
C6 C5 1.340(13)
C6 C7 1.528(14)
C11 C16 1.329(14)
C11 C10 1.451(12)
C11 C12 1.551(15)
C19 C18 1.566(14)
C19 C10 1.616(14)
C19 H19 1.0000
O9 C17 1.397(12)
O9 C9 1.426(12)
C5 C18 1.601(14)
C1 O2 1.363(13)
C1 C18 1.482(14)
C17 C16 1.478(14)
C17 C18 1.605(13)
C17 H17 1.0000
O14 C15 1.325(15)
O14 C13 1.469(15)
C16 C15 1.421(16)
C7 C8 1.451(16)
C7 H7 1.0000
C10 C9 1.464(18)
C10 H10 1.0000
C8 C9 1.603(17)
C8 H8A 0.9900
C8 H8B 0.9900
C9 H9 1.0000
C3 O2 1.413(13)
C3 H3A 0.9900
C3 H3B 0.9900
C12 C13 1.444(19)
C12 H12A 0.9900
C12 H12B 0.9900
C13 H13A 0.9900
C13 H13B 0.9900
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C12 H12A O15 0.99 2.27 3.113(16) 142.9 2
C10 H10 O15 1.00 2.39 3.218(14) 140.1 2
C7 H7 O14 1.00 2.45 3.168(13) 128.0 4_675
C4 H4B O1 0.99 2.34 3.205(12) 145.1 3_665
C12 H12A O15 0.99 2.27 3.113(16) 142.9 2
C10 H10 O15 1.00 2.39 3.218(14) 140.1 2
C7 H7 O14 1.00 2.45 3.168(13) 128.0 4_675
C4 H4B O1 0.99 2.34 3.205(12) 145.1 3_665
C4 H4B O1 0.99 2.34 3.205(12) 145.1 3_665
C7 H7 O14 1.00 2.45 3.168(13) 128.0 4_675
C10 H10 O15 1.00 2.39 3.218(14) 140.1 2
C12 H12A O15 0.99 2.27 3.113(16) 142.9 2
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
C21 C20 C6 C5 -176.7(10)
C21 C20 C6 C7 15.8(16)
C7 O7 C19 C18 -48.7(11)
C7 O7 C19 C10 69.1(10)
C20 C6 C5 C4 -2.7(16)
C7 C6 C5 C4 164.7(9)
C20 C6 C5 C18 -175.6(9)
C7 C6 C5 C18 -8.3(14)
C3 C4 C5 C6 175.9(10)
C3 C4 C5 C18 -11.0(12)
C9 O9 C17 C16 -54.8(10)
C9 O9 C17 C18 61.4(10)
C10 C11 C16 C15 -166.3(10)
C12 C11 C16 C15 4.9(14)
C10 C11 C16 C17 3.8(12)
C12 C11 C16 C17 175.1(8)
O9 C17 C16 C11 52.2(10)
C18 C17 C16 C11 -64.0(10)
O9 C17 C16 C15 -137.6(9)
C18 C17 C16 C15 106.2(10)
O1 C1 C18 C19 -27.9(12)
O2 C1 C18 C19 152.4(8)
O1 C1 C18 C5 -153.4(9)
O2 C1 C18 C5 27.0(12)
O1 C1 C18 C17 92.4(11)
O2 C1 C18 C17 -87.3(11)
O7 C19 C18 C1 -121.0(9)
C10 C19 C18 C1 118.2(8)
O7 C19 C18 C5 5.2(11)
C10 C19 C18 C5 -115.5(8)
O7 C19 C18 C17 118.9(9)
C10 C19 C18 C17 -1.8(11)
C6 C5 C18 C1 148.9(9)
C4 C5 C18 C1 -24.5(12)
C6 C5 C18 C19 23.1(12)
C4 C5 C18 C19 -150.4(8)
C6 C5 C18 C17 -93.9(10)
C4 C5 C18 C17 92.7(9)
O9 C17 C18 C1 179.1(9)
C16 C17 C18 C1 -61.9(11)
O9 C17 C18 C19 -59.1(11)
C16 C17 C18 C19 60.0(10)
O9 C17 C18 C5 59.2(9)
C16 C17 C18 C5 178.2(8)
C13 O14 C15 O15 170.5(10)
C13 O14 C15 C16 -15.5(15)
C11 C16 C15 O15 163.5(10)
C17 C16 C15 O15 -5.4(16)
C11 C16 C15 O14 -10.3(15)
C17 C16 C15 O14 -179.2(9)
C19 O7 C7 C8 -62.0(11)
C19 O7 C7 C6 63.6(10)
C5 C6 C7 O7 -33.0(12)
C20 C6 C7 O7 134.9(9)
C5 C6 C7 C8 88.2(12)
C20 C6 C7 C8 -103.9(11)
C16 C11 C10 C9 -56.4(11)
C12 C11 C10 C9 133.3(10)
C16 C11 C10 C19 59.8(12)
C12 C11 C10 C19 -110.5(11)
O7 C19 C10 C11 178.4(9)
C18 C19 C10 C11 -55.7(12)
O7 C19 C10 C9 -63.4(10)
C18 C19 C10 C9 62.4(10)
O7 C7 C8 C9 49.9(12)
C6 C7 C8 C9 -72.6(12)
C17 O9 C9 C10 1.8(11)
C17 O9 C9 C8 -116.4(9)
C11 C10 C9 O9 52.0(11)
C19 C10 C9 O9 -66.9(10)
C11 C10 C9 C8 169.9(8)
C19 C10 C9 C8 51.0(11)
C7 C8 C9 O9 68.0(12)
C7 C8 C9 C10 -50.9(13)
C5 C4 C3 O2 48.9(12)
C16 C11 C12 C13 24.4(13)
C10 C11 C12 C13 -165.5(10)
C11 C12 C13 O14 -49.3(14)
C15 O14 C13 C12 47.3(16)
O1 C1 O2 C3 -169.8(8)
C18 C1 O2 C3 9.8(12)
C4 C3 O2 C1 -50.3(11)
