#------------------------------------------------------------------------------
#$Date: 2020-12-02 02:12:35 +0200 (Wed, 02 Dec 2020) $
#$Revision: 259419 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/96/1559692.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_1559692
loop_
_publ_author_name
'Yang, Yue'
'Gong, Qi'
'Wang, Wei'
'Mao, Ying-Le'
'Wang, Xiao-Rong'
'Yao, Sheng'
'Zhang, Hai-Yan'
'Tang, Chunping'
'Ye, Yang'
_publ_section_title
;
 Neuroprotective and Anti-inflammatory Ditetrahydrofuran-Containing
 Diarylheptanoids from Tacca chantrieri.
;
_journal_name_full               'Journal of natural products'
_journal_paper_doi               10.1021/acs.jnatprod.0c00901
_journal_year                    2020
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C38 H38 O8, 4(C5 H5 N)'
_chemical_formula_sum            'C58 H58 N4 O8'
_chemical_formula_weight         939.08
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.939(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   31.360(5)
_cell_length_b                   5.4501(8)
_cell_length_c                   14.626(2)
_cell_measurement_reflns_used    3012
_cell_measurement_temperature    173
_cell_measurement_theta_max      54.708
_cell_measurement_theta_min      2.829
_cell_volume                     2490.5(6)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.0
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            33190
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.546
_diffrn_reflns_theta_min         2.829
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.673
_exptl_absorpt_correction_T_max  0.7534
_exptl_absorpt_correction_T_min  0.5917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1081 before and 0.0662 after correction. The Ratio of minimum to maximum transmission is 0.7854. The λ/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_description       block
_exptl_crystal_F_000             996
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.096
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 1722 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         4490
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0312
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0461P)²+0.3938P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0777
_refine_ls_wR_factor_ref         0.0791
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_full    0.934
_reflns_Friedel_fraction_max     0.897
_reflns_number_gt                4257
_reflns_number_total             4490
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            np0c00901_si_003.cif
_cod_data_source_block           cu_20180574_0m
_cod_original_cell_volume        2490.4(7)
_cod_database_code               1559692
_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_max   0.930
_shelx_estimated_absorpt_t_min   0.889
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C2(H2), C1(H1A)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C6(H6A,H6C), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C3B(H3B), C2B(H2B), C6B(H6B), C5B(H5B), C2A(H2A), C3A(H3A), C5A(H5A),
 C6A(H6AA), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C17(H17)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-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 0.17194(4) 0.2431(3) 0.72363(10) 0.0531(4) Uani 1 1 d . . . . .
H1 H 0.1789 0.1572 0.7702 0.080 Uiso 1 1 calc GR . . . .
O2 O 0.38467(4) 1.0316(3) 0.55236(11) 0.0510(4) Uani 1 1 d . . . . .
O3 O 0.46664(4) 0.6663(3) 0.38243(9) 0.0556(4) Uani 1 1 d . . . . .
O4 O 0.60123(5) 0.7447(3) 0.08474(9) 0.0607(4) Uani 1 1 d . . . . .
H4 H 0.5891 0.8435 0.0469 0.091 Uiso 1 1 calc GR . . . .
C3B C 0.20011(6) 0.5702(4) 0.64131(14) 0.0487(5) Uani 1 1 d . . . . .
H3B H 0.1719 0.6115 0.6175 0.058 Uiso 1 1 calc R . . . .
C2B C 0.23454(6) 0.7094(4) 0.61751(14) 0.0486(5) Uani 1 1 d . . . . .
H2B H 0.2294 0.8446 0.5770 0.058 Uiso 1 1 calc R . . . .
C1B C 0.27611(6) 0.6562(4) 0.65121(13) 0.0435(4) Uani 1 1 d . . . . .
C6B C 0.28211(6) 0.4536(4) 0.70812(14) 0.0471(5) Uani 1 1 d . . . . .
H6B H 0.3103 0.4113 0.7316 0.056 Uiso 1 1 calc R . . . .
C5B C 0.24813(6) 0.3108(4) 0.73180(13) 0.0445(4) Uani 1 1 d . . . . .
H5B H 0.2533 0.1713 0.7701 0.053 Uiso 1 1 calc R . . . .
C4B C 0.20685(6) 0.3710(4) 0.69972(13) 0.0415(4) Uani 1 1 d . . . . .
C7 C 0.31367(6) 0.8095(4) 0.62611(15) 0.0506(5) Uani 1 1 d . . . . .
H7A H 0.3330 0.8411 0.6820 0.061 Uiso 1 1 calc R . . . .
H7B H 0.3031 0.9696 0.6016 0.061 Uiso 1 1 calc R . . . .
C6 C 0.33862(6) 0.6827(4) 0.55488(13) 0.0438(4) Uani 1 1 d . . . . .
H6A H 0.3483 0.5206 0.5792 0.053 Uiso 1 1 calc R . . . .
H6C H 0.3191 0.6534 0.4991 0.053 Uiso 1 1 calc R . . . .
C5 C 0.37712(5) 0.8231(4) 0.52792(12) 0.0390(4) Uani 1 1 d . . . . .
C4 C 0.40476(6) 0.6843(4) 0.46630(12) 0.0413(4) Uani 1 1 d . . . . .
H4A H 0.3877 0.6489 0.4077 0.050 Uiso 1 1 calc R . . . .
H4B H 0.4128 0.5251 0.4956 0.050 Uiso 1 1 calc R . . . .
C3 C 0.44546(5) 0.8176(4) 0.44528(11) 0.0394(4) Uani 1 1 d . . . . .
H3 H 0.4374 0.9765 0.4143 0.047 Uiso 1 1 calc R . . . .
C2 C 0.47915(5) 0.8681(3) 0.52400(10) 0.0313(3) Uani 1 1 d . . . . .
H2 H 0.4743 1.0293 0.5540 0.038 Uiso 1 1 calc R . . . .
C1 C 0.51231(5) 0.6626(3) 0.40519(11) 0.0362(4) Uani 1 1 d . . . . .
H1A H 0.5203 0.5023 0.4352 0.043 Uiso 1 1 calc R . . . .
C1A C 0.53516(5) 0.6851(3) 0.31867(10) 0.0333(4) Uani 1 1 d . . . . .
C2A C 0.52703(6) 0.8799(4) 0.25901(12) 0.0391(4) Uani 1 1 d . . . . .
H2A H 0.5065 1.0001 0.2723 0.047 Uiso 1 1 calc R . . . .
C3A C 0.54827(6) 0.9028(4) 0.18013(12) 0.0412(4) Uani 1 1 d . . . . .
H3A H 0.5422 1.0376 0.1399 0.049 Uiso 1 1 calc R . . . .
C4A C 0.57847(6) 0.7284(4) 0.15996(12) 0.0401(4) Uani 1 1 d . . . . .
C5A C 0.58637(6) 0.5320(4) 0.21860(13) 0.0432(4) Uani 1 1 d . . . . .
H5A H 0.6067 0.4109 0.2052 0.052 Uiso 1 1 calc R . . . .
C6A C 0.56480(6) 0.5108(3) 0.29686(12) 0.0386(4) Uani 1 1 d . . . . .
H6AA H 0.5704 0.3741 0.3364 0.046 Uiso 1 1 calc R . . . .
N1 N 0.42395(6) 0.0697(4) 0.05159(13) 0.0570(5) Uani 1 1 d . . . . .
C8 C 0.44699(8) 0.2697(5) 0.04727(19) 0.0674(7) Uani 1 1 d . . . . .
H8 H 0.4589 0.3058 -0.0087 0.081 Uiso 1 1 calc R . . . .
C9 C 0.45463(9) 0.4273(6) 0.1183(2) 0.0824(9) Uani 1 1 d . . . . .
H9 H 0.4722 0.5675 0.1122 0.099 Uiso 1 1 calc R . . . .
C10 C 0.43696(9) 0.3835(6) 0.1988(2) 0.0840(10) Uani 1 1 d . . . . .
H10 H 0.4417 0.4927 0.2493 0.101 Uiso 1 1 calc R . . . .
C11 C 0.41183(9) 0.1751(6) 0.20507(17) 0.0765(8) Uani 1 1 d . . . . .
H11 H 0.3986 0.1391 0.2595 0.092 Uiso 1 1 calc R . . . .
C12 C 0.40680(8) 0.0236(5) 0.13040(15) 0.0593(6) Uani 1 1 d . . . . .
H12 H 0.3903 -0.1216 0.1347 0.071 Uiso 1 1 calc R . . . .
N2 N 0.31089(5) 0.4568(3) 0.11755(12) 0.0470(4) Uani 1 1 d . . . . .
C13 C 0.33179(6) 0.4796(4) 0.04248(15) 0.0494(5) Uani 1 1 d . . . . .
H13 H 0.3490 0.6212 0.0370 0.059 Uiso 1 1 calc R . . . .
C14 C 0.32993(7) 0.3103(5) -0.02769(15) 0.0547(5) Uani 1 1 d . . . . .
H14 H 0.3453 0.3355 -0.0801 0.066 Uiso 1 1 calc R . . . .
C15 C 0.30521(7) 0.1034(4) -0.02006(15) 0.0526(5) Uani 1 1 d . . . . .
H15 H 0.3033 -0.0180 -0.0668 0.063 Uiso 1 1 calc R . . . .
C16 C 0.28346(7) 0.0773(4) 0.05670(15) 0.0501(5) Uani 1 1 d . . . . .
H16 H 0.2662 -0.0635 0.0641 0.060 Uiso 1 1 calc R . . . .
C17 C 0.28681(6) 0.2570(4) 0.12306(14) 0.0468(5) Uani 1 1 d . . . . .
H17 H 0.2712 0.2376 0.1754 0.056 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 0.0181 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'
N N 0.0311 0.0180 '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
C4B O1 H1 109.5 . . ?
C3 O3 C1 111.37(13) . . ?
C4A O4 H4 109.5 . . ?
C2B C3B H3B 119.9 . . ?
C4B C3B H3B 119.9 . . ?
C4B C3B C2B 120.12(18) . . ?
C3B C2B H2B 119.2 . . ?
C1B C2B C3B 121.7(2) . . ?
C1B C2B H2B 119.2 . . ?
C2B C1B C6B 117.13(18) . . ?
C2B C1B C7 121.75(19) . . ?
C6B C1B C7 121.11(18) . . ?
C1B C6B H6B 119.0 . . ?
C1B C6B C5B 121.97(18) . . ?
C5B C6B H6B 119.0 . . ?
C6B C5B H5B 120.0 . . ?
C4B C5B C6B 120.02(19) . . ?
C4B C5B H5B 120.0 . . ?
O1 C4B C3B 118.26(17) . . ?
O1 C4B C5B 122.70(18) . . ?
C5B C4B C3B 119.04(18) . . ?
C1B C7 H7A 109.3 . . ?
C1B C7 H7B 109.3 . . ?
C1B C7 C6 111.83(17) . . ?
H7A C7 H7B 107.9 . . ?
C6 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
C7 C6 H6A 108.6 . . ?
C7 C6 H6C 108.6 . . ?
H6A C6 H6C 107.6 . . ?
C5 C6 C7 114.73(17) . . ?
C5 C6 H6A 108.6 . . ?
C5 C6 H6C 108.6 . . ?
O2 C5 C6 122.69(17) . . ?
O2 C5 C4 122.74(17) . . ?
C4 C5 C6 114.56(16) . . ?
C5 C4 H4A 108.6 . . ?
C5 C4 H4B 108.6 . . ?
C5 C4 C3 114.60(17) . . ?
H4A C4 H4B 107.6 . . ?
C3 C4 H4A 108.6 . . ?
C3 C4 H4B 108.6 . . ?
O3 C3 C4 107.25(15) . . ?
O3 C3 H3 108.7 . . ?
O3 C3 C2 104.99(14) . . ?
C4 C3 H3 108.7 . . ?
C2 C3 C4 118.28(14) . . ?
C2 C3 H3 108.7 . . ?
C3 C2 C2 102.56(15) . 2_656 ?
C3 C2 H2 111.7 . . ?
C3 C2 C1 116.69(15) . 2_656 ?
C2 C2 H2 111.7 2_656 . ?
C1 C2 C2 101.69(12) 2_656 2_656 ?
C1 C2 H2 111.7 2_656 . ?
O3 C1 C2 104.94(13) . 2_656 ?
O3 C1 H1A 108.6 . . ?
O3 C1 C1A 109.78(13) . . ?
C2 C1 H1A 108.6 2_656 . ?
C1A C1 C2 116.00(14) . 2_656 ?
C1A C1 H1A 108.6 . . ?
C2A C1A C1 121.01(15) . . ?
C2A C1A C6A 118.14(15) . . ?
C6A C1A C1 120.84(15) . . ?
C1A C2A H2A 119.4 . . ?
C1A C2A C3A 121.22(16) . . ?
C3A C2A H2A 119.4 . . ?
C2A C3A H3A 120.0 . . ?
C2A C3A C4A 119.94(16) . . ?
C4A C3A H3A 120.0 . . ?
O4 C4A C3A 122.61(16) . . ?
O4 C4A C5A 118.23(16) . . ?
C5A C4A C3A 119.15(15) . . ?
C4A C5A H5A 119.9 . . ?
C4A C5A C6A 120.29(16) . . ?
C6A C5A H5A 119.9 . . ?
C1A C6A H6AA 119.4 . . ?
C5A C6A C1A 121.24(16) . . ?
C5A C6A H6AA 119.4 . . ?
C8 N1 C12 117.5(2) . . ?
N1 C8 H8 118.2 . . ?
N1 C8 C9 123.5(3) . . ?
C9 C8 H8 118.2 . . ?
C8 C9 H9 120.2 . . ?
C8 C9 C10 119.5(3) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 H10 120.8 . . ?
C9 C10 C11 118.3(2) . . ?
C11 C10 H10 120.8 . . ?
C10 C11 H11 121.0 . . ?
C12 C11 C10 117.9(3) . . ?
C12 C11 H11 121.0 . . ?
N1 C12 C11 123.2(3) . . ?
N1 C12 H12 118.4 . . ?
C11 C12 H12 118.4 . . ?
C17 N2 C13 116.60(18) . . ?
N2 C13 H13 118.0 . . ?
N2 C13 C14 124.0(2) . . ?
C14 C13 H13 118.0 . . ?
C13 C14 H14 120.8 . . ?
C13 C14 C15 118.4(2) . . ?
C15 C14 H14 120.8 . . ?
C14 C15 H15 120.8 . . ?
C16 C15 C14 118.3(2) . . ?
C16 C15 H15 120.8 . . ?
C15 C16 H16 120.3 . . ?
C15 C16 C17 119.4(2) . . ?
C17 C16 H16 120.3 . . ?
N2 C17 C16 123.26(19) . . ?
N2 C17 H17 118.4 . . ?
C16 C17 H17 118.4 . . ?
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 H1 0.8400 . ?
O1 C4B 1.369(2) . ?
O2 C5 1.209(3) . ?
O3 C3 1.439(2) . ?
O3 C1 1.442(2) . ?
O4 H4 0.8400 . ?
O4 C4A 1.365(2) . ?
C3B H3B 0.9500 . ?
C3B C2B 1.388(3) . ?
C3B C4B 1.386(3) . ?
C2B H2B 0.9500 . ?
C2B C1B 1.384(3) . ?
C1B C6B 1.386(3) . ?
C1B C7 1.515(3) . ?
C6B H6B 0.9500 . ?
C6B C5B 1.387(3) . ?
C5B H5B 0.9500 . ?
C5B C4B 1.378(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C6 1.522(3) . ?
C6 H6A 0.9900 . ?
C6 H6C 0.9900 . ?
C6 C5 1.510(3) . ?
C5 C4 1.507(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C3 1.523(2) . ?
C3 H3 1.0000 . ?
C3 C2 1.519(2) . ?
C2 C2 1.537(3) 2_656 ?
C2 H2 1.0000 . ?
C2 C1 1.533(2) 2_656 ?
C1 C2 1.533(2) 2_656 ?
C1 H1A 1.0000 . ?
C1 C1A 1.512(2) . ?
C1A C2A 1.384(3) . ?
C1A C6A 1.386(2) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.387(2) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.392(3) . ?
C4A C5A 1.381(3) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.383(3) . ?
C6A H6AA 0.9500 . ?
N1 C8 1.312(3) . ?
N1 C12 1.337(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.354(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.365(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.390(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.367(4) . ?
C12 H12 0.9500 . ?
N2 C13 1.332(3) . ?
N2 C17 1.331(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.377(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.378(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.370(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.376(3) . ?
C17 H17 0.9500 . ?
