#------------------------------------------------------------------------------
#$Date: 2021-01-07 07:01:03 +0200 (Thu, 07 Jan 2021) $
#$Revision: 260721 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/72/7127224.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_7127224
loop_
_publ_author_name
'Zhao, Can'
'Khan, Ijaz'
'Zhang, Yong Jian'
_publ_section_title
;
 Enantioselective total synthesis of furofuran lignans via
 Pd-catalyzed asymmetric allylic cycloadditon of vinylethylene carbonates
 with 2-nitroacrylates.
;
_journal_issue                   82
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              12431
_journal_page_last               12434
_journal_paper_doi               10.1039/d0cc05640e
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H12 O5'
_chemical_formula_sum            'C13 H12 O5'
_chemical_formula_weight         248.23
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2020-07-12 deposited with the CCDC.	2020-09-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.6885(3)
_cell_length_b                   7.1093(3)
_cell_length_c                   24.1880(9)
_cell_measurement_reflns_used    8692
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      68.28
_cell_measurement_theta_min      3.65
_cell_volume                     1150.15(8)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1044
_diffrn_reflns_av_unetI/netI     0.0631
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            12764
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.391
_diffrn_reflns_theta_min         3.655
_exptl_absorpt_coefficient_mu    0.938
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.150
_exptl_transmission_factor_max   0.7531
_exptl_transmission_factor_min   0.6575
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details
;
 Flack x determined using 572 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(9)
_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     163
_refine_ls_number_reflns         2095
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0329
_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)+(0.0522P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0898
_reflns_Friedel_coverage         0.676
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                1610
_reflns_number_total             2095
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc05640e2.cif
_cod_data_source_block           ta_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_absolute_configuration' value 'AD' was changed
to 'ad' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7127223--7127224.cif.
;
_cod_database_code               7127224
_shelx_shelxl_version_number     2016/6
_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   0.849
_shelx_estimated_absorpt_t_max   0.872
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.9581(3) 0.6850(2) 0.40818(8) 0.0528(5) Uani 1 1 d . . . . .
C1 C 1.0710(4) 0.9096(4) 0.29127(12) 0.0546(6) Uani 1 1 d . . . . .
O2 O 0.9306(3) 0.8575(3) 0.25413(8) 0.0677(6) Uani 1 1 d . . . . .
C2 C 0.9779(3) 0.9439(3) 0.34691(11) 0.0453(6) Uani 1 1 d . . . . .
H2 H 0.964744 1.078529 0.354753 0.054 Uiso 1 1 calc R U . . .
O3 O 1.2437(3) 0.9197(3) 0.27898(10) 0.0758(6) Uani 1 1 d . . . . .
C3 C 1.0828(4) 0.8402(4) 0.39387(12) 0.0556(6) Uani 1 1 d . . . . .
H3A H 1.213216 0.796283 0.381978 0.067 Uiso 1 1 calc R U . . .
H3B H 1.100386 0.922880 0.425399 0.067 Uiso 1 1 calc R U . . .
C6 C 0.8192(4) 0.6526(3) 0.36402(10) 0.0432(5) Uani 1 1 d . . . . .
H6 H 0.885028 0.578295 0.335146 0.052 Uiso 1 1 calc R U . . .
O5 O 0.2757(3) 0.5234(3) 0.49826(8) 0.0594(5) Uani 1 1 d . . . . .
C5 C 0.7740(4) 0.8488(3) 0.34146(11) 0.0451(5) Uani 1 1 d . . . . .
H5 H 0.670386 0.913398 0.362915 0.054 Uiso 1 1 calc R U . . .
O4 O 0.1420(3) 0.2836(3) 0.44552(9) 0.0649(6) Uani 1 1 d . . . . .
C4 C 0.7337(4) 0.8564(4) 0.27965(12) 0.0603(7) Uani 1 1 d . . . . .
H4A H 0.657523 0.747485 0.267837 0.072 Uiso 1 1 calc R U . . .
H4B H 0.659920 0.969290 0.270072 0.072 Uiso 1 1 calc R U . . .
C7 C 0.6419(4) 0.5459(3) 0.38517(10) 0.0422(5) Uani 1 1 d . . . . .
C9 C 0.3854(3) 0.5015(3) 0.45107(10) 0.0425(5) Uani 1 1 d . . . . .
C8 C 0.5532(3) 0.5970(3) 0.43562(10) 0.0423(5) Uani 1 1 d . . . . .
H8 H 0.606582 0.691885 0.457565 0.051 Uiso 1 1 calc R U . . .
C10 C 0.3046(4) 0.3587(3) 0.41924(11) 0.0464(6) Uani 1 1 d . . . . .
C11 C 0.3884(4) 0.3055(4) 0.37054(12) 0.0561(7) Uani 1 1 d . . . . .
H11 H 0.333716 0.209503 0.349235 0.067 Uiso 1 1 calc R U . . .
C12 C 0.5603(4) 0.4015(3) 0.35390(11) 0.0519(6) Uani 1 1 d . . . . .
H12 H 0.621887 0.367661 0.320892 0.062 Uiso 1 1 calc R U . . .
C13 C 0.1168(4) 0.3884(4) 0.49522(13) 0.0643(8) Uani 1 1 d . . . . .
H13A H 0.121465 0.305028 0.526946 0.077 Uiso 1 1 calc R U . . .
H13B H -0.011573 0.451889 0.495037 0.077 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 '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
_geom_angle_publ_flag
C3 O1 C6 108.83(18) . . ?
O3 C1 O2 121.5(3) . . ?
O3 C1 C2 127.9(3) . . ?
O2 C1 C2 110.6(2) . . ?
C1 O2 C4 110.4(2) . . ?
C1 C2 C3 113.4(2) . . ?
C1 C2 C5 102.8(2) . . ?
C3 C2 C5 105.16(19) . . ?
C1 C2 H2 111.7 . . ?
C3 C2 H2 111.7 . . ?
C5 C2 H2 111.7 . . ?
O1 C3 C2 106.6(2) . . ?
O1 C3 H3A 110.4 . . ?
C2 C3 H3A 110.4 . . ?
O1 C3 H3B 110.4 . . ?
C2 C3 H3B 110.4 . . ?
H3A C3 H3B 108.6 . . ?
O1 C6 C7 109.9(2) . . ?
O1 C6 C5 104.30(18) . . ?
C7 C6 C5 115.3(2) . . ?
O1 C6 H6 109.0 . . ?
C7 C6 H6 109.0 . . ?
C5 C6 H6 109.0 . . ?
C9 O5 C13 106.19(19) . . ?
C4 C5 C2 103.2(2) . . ?
C4 C5 C6 114.7(2) . . ?
C2 C5 C6 101.33(19) . . ?
C4 C5 H5 112.2 . . ?
C2 C5 H5 112.2 . . ?
C6 C5 H5 112.2 . . ?
C10 O4 C13 106.40(19) . . ?
O2 C4 C5 104.9(2) . . ?
O2 C4 H4A 110.8 . . ?
C5 C4 H4A 110.8 . . ?
O2 C4 H4B 110.8 . . ?
C5 C4 H4B 110.8 . . ?
H4A C4 H4B 108.8 . . ?
C12 C7 C8 119.9(2) . . ?
C12 C7 C6 120.0(2) . . ?
C8 C7 C6 120.0(2) . . ?
C8 C9 O5 127.9(2) . . ?
C8 C9 C10 122.3(2) . . ?
O5 C9 C10 109.8(2) . . ?
C9 C8 C7 117.2(2) . . ?
C9 C8 H8 121.4 . . ?
C7 C8 H8 121.4 . . ?
C11 C10 O4 128.5(2) . . ?
C11 C10 C9 121.7(2) . . ?
O4 C10 C9 109.8(2) . . ?
C10 C11 C12 117.0(2) . . ?
C10 C11 H11 121.5 . . ?
C12 C11 H11 121.5 . . ?
C7 C12 C11 121.9(2) . . ?
C7 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
O4 C13 O5 107.8(2) . . ?
O4 C13 H13A 110.1 . . ?
O5 C13 H13A 110.1 . . ?
O4 C13 H13B 110.1 . . ?
O5 C13 H13B 110.1 . . ?
H13A C13 H13B 108.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.426(3) . ?
O1 C6 1.434(3) . ?
C1 O3 1.195(3) . ?
C1 O2 1.351(4) . ?
C1 C2 1.503(4) . ?
O2 C4 1.455(3) . ?
C2 C3 1.525(4) . ?
C2 C5 1.527(3) . ?
C2 H2 0.9800 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C6 C7 1.497(3) . ?
C6 C5 1.528(3) . ?
C6 H6 0.9800 . ?
O5 C9 1.366(3) . ?
O5 C13 1.434(3) . ?
C5 C4 1.520(3) . ?
C5 H5 0.9800 . ?
O4 C10 1.368(3) . ?
O4 C13 1.424(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C7 C12 1.387(3) . ?
C7 C8 1.405(3) . ?
C9 C8 1.364(3) . ?
C9 C10 1.384(3) . ?
C8 H8 0.9300 . ?
C10 C11 1.358(4) . ?
C11 C12 1.397(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C1 O2 C4 179.9(3) . . . . ?
C2 C1 O2 C4 1.5(3) . . . . ?
O3 C1 C2 C3 -49.1(4) . . . . ?
O2 C1 C2 C3 129.2(2) . . . . ?
O3 C1 C2 C5 -162.0(3) . . . . ?
O2 C1 C2 C5 16.2(3) . . . . ?
C6 O1 C3 C2 17.1(3) . . . . ?
C1 C2 C3 O1 -104.6(2) . . . . ?
C5 C2 C3 O1 7.0(3) . . . . ?
C3 O1 C6 C7 -158.5(2) . . . . ?
C3 O1 C6 C5 -34.4(2) . . . . ?
C1 C2 C5 C4 -26.3(2) . . . . ?
C3 C2 C5 C4 -145.2(2) . . . . ?
C1 C2 C5 C6 92.8(2) . . . . ?
C3 C2 C5 C6 -26.2(3) . . . . ?
O1 C6 C5 C4 147.02(19) . . . . ?
C7 C6 C5 C4 -92.4(3) . . . . ?
O1 C6 C5 C2 36.7(2) . . . . ?
C7 C6 C5 C2 157.2(2) . . . . ?
C1 O2 C4 C5 -18.9(3) . . . . ?
C2 C5 C4 O2 27.8(3) . . . . ?
C6 C5 C4 O2 -81.5(3) . . . . ?
O1 C6 C7 C12 -138.5(2) . . . . ?
C5 C6 C7 C12 104.0(3) . . . . ?
O1 C6 C7 C8 44.1(3) . . . . ?
C5 C6 C7 C8 -73.4(3) . . . . ?
C13 O5 C9 C8 -179.1(2) . . . . ?
C13 O5 C9 C10 -0.7(3) . . . . ?
O5 C9 C8 C7 178.8(2) . . . . ?
C10 C9 C8 C7 0.6(3) . . . . ?
C12 C7 C8 C9 -1.1(3) . . . . ?
C6 C7 C8 C9 176.3(2) . . . . ?
C13 O4 C10 C11 179.5(3) . . . . ?
C13 O4 C10 C9 1.8(3) . . . . ?
C8 C9 C10 C11 0.0(4) . . . . ?
O5 C9 C10 C11 -178.6(2) . . . . ?
C8 C9 C10 O4 177.8(2) . . . . ?
O5 C9 C10 O4 -0.7(3) . . . . ?
O4 C10 C11 C12 -177.4(2) . . . . ?
C9 C10 C11 C12 0.0(4) . . . . ?
C8 C7 C12 C11 1.1(4) . . . . ?
C6 C7 C12 C11 -176.3(2) . . . . ?
C10 C11 C12 C7 -0.6(4) . . . . ?
C10 O4 C13 O5 -2.2(3) . . . . ?
C9 O5 C13 O4 1.8(3) . . . . ?
