#------------------------------------------------------------------------------
#$Date: 2021-07-01 04:14:44 +0300 (Thu, 01 Jul 2021) $
#$Revision: 266827 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/38/1563816.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_1563816
loop_
_publ_author_name
'Sun, Jiawei'
'Gu, Wei'
'Yang, He'
'Tang, Wenjun'
_publ_section_title
;
 Enantioselective Total Synthesis of Parnafungin A1 and
 10a-epi-Hirtusneanine
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC02919C
_journal_year                    2021
_chemical_formula_moiety         'C18 H20 O8'
_chemical_formula_sum            'C18 H20 O8'
_chemical_formula_weight         364.355
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     iterative
_audit_creation_date             2021-01-31
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-03-05 deposited with the CCDC.	2021-06-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.300(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2810(4)
_cell_length_b                   26.6332(13)
_cell_length_c                   8.0706(4)
_cell_measurement_reflns_used    9560
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.33
_cell_measurement_theta_min      3.32
_cell_volume                     1724.82(15)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293.4
_diffrn_measured_fraction_theta_full 0.9781
_diffrn_measured_fraction_theta_max 0.9781
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.9781
_diffrn_reflns_Laue_measured_fraction_max 0.9781
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            23450
_diffrn_reflns_point_group_measured_fraction_full 0.9781
_diffrn_reflns_point_group_measured_fraction_max 0.9781
_diffrn_reflns_theta_full        65.4999
_diffrn_reflns_theta_max         65.50
_diffrn_reflns_theta_min         3.32
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.942
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5945
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1397 before and 0.0875 after correction.
The Ratio of minimum to maximum transmission is 0.7892.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             770.980
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.3883
_refine_diff_density_min         -0.4083
_refine_diff_density_rms         0.0860
_refine_ls_d_res_high            0.8472
_refine_ls_d_res_low             13.3166
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.2020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    33
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2904
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.2020
_refine_ls_R_factor_all          0.0926
_refine_ls_R_factor_gt           0.0907
_refine_ls_shift/su_max          17.3621
_refine_ls_shift/su_mean         0.5147
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1101P)²+3.7995P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2789
_refine_ls_wR_factor_ref         0.2800
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              31
_reflns_limit_k_min              0
_reflns_limit_l_max              9
_reflns_limit_l_min              0
_reflns_number_gt                2746
_reflns_number_total             2904
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d1sc02919c2.cif
_cod_data_source_block           d8v20639
_cod_database_code               1563816
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.9980(5)
 0.0020(5)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3.a Ternary CH refined with riding coordinates:
 C10(H10), C11(H11), C12(H12)
3.b Secondary CH2 refined with riding coordinates:
 C18(H18a,H18b)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4a)
3.d Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c), C16(H16a,H16b,H16c), C17(H17a,H17b,H17c)
3.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4), O5(H5), O6(H6)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 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_refinement_flags_posn
O1 O -0.1150(4) 0.57235(13) 0.3810(6) 0.0661(12) Uani 1.000000 .
H1 H -0.0556(10) 0.5487(8) 0.423(9) 0.0991(17) Uiso 1.000000 GR
O2 O 0.1684(4) 0.52806(11) 0.5383(5) 0.0557(10) Uani 1.000000 .
O3 O 0.4056(3) 0.66248(11) 0.5385(4) 0.0427(8) Uani 1.000000 .
O4 O 0.4562(4) 0.49080(11) 0.6852(5) 0.0573(10) Uani 1.000000 .
H4 H 0.3561(19) 0.49042(12) 0.639(8) 0.0859(15) Uiso 1.000000 GR
O5 O 0.7047(4) 0.68389(12) 0.7890(4) 0.0518(9) Uani 1.000000 .
H5 H 0.699(8) 0.7039(5) 0.7106(4) 0.0776(14) Uiso 1.000000 GR
O6 O -0.2431(4) 0.73905(13) 0.0924(5) 0.0564(10) Uani 1.000000 .
H6 H -0.2786(6) 0.7626(16) 0.139(7) 0.0847(15) Uiso 1.000000 GR
O7 O 0.3118(6) 0.68826(15) 0.8206(6) 0.0786(14) Uani 1.000000 .
O8 O 0.4552(5) 0.62643(14) 0.9735(4) 0.0607(10) Uani 1.000000 .
C1 C -0.0194(5) 0.61319(16) 0.3772(6) 0.0435(11) Uani 1.000000 .
C2 C -0.0924(6) 0.65393(17) 0.2818(6) 0.0466(11) Uani 1.000000 .
H2 H -0.2054(6) 0.65337(17) 0.2276(6) 0.0559(14) Uiso 1.000000 R
C3 C 0.0033(6) 0.69582(16) 0.2670(5) 0.0413(10) Uani 1.000000 .
C4 C 0.1688(5) 0.69874(15) 0.3569(5) 0.0381(10) Uani 1.000000 .
H4a H 0.2316(5) 0.72722(15) 0.3494(5) 0.0458(12) Uiso 1.000000 R
C5 C 0.2389(5) 0.65873(15) 0.4579(5) 0.0360(10) Uani 1.000000 .
C6 C 0.1506(5) 0.61448(15) 0.4679(5) 0.0377(10) Uani 1.000000 .
C7 C 0.2363(6) 0.57093(15) 0.5546(5) 0.0411(10) Uani 1.000000 .
C8 C 0.4067(5) 0.57789(15) 0.6494(5) 0.0375(10) Uani 1.000000 .
C9 C 0.5090(6) 0.53809(16) 0.7064(6) 0.0437(11) Uani 1.000000 .
C10 C 0.6912(6) 0.54228(18) 0.7931(7) 0.0526(12) Uani 1.000000 .
H10 H 0.7531(6) 0.53056(18) 0.7115(7) 0.0632(15) Uiso 1.000000 R
C11 C 0.7503(5) 0.59591(17) 0.8450(6) 0.0444(11) Uani 1.000000 .
H11 H 0.7298(5) 0.60266(17) 0.9574(6) 0.0533(13) Uiso 1.000000 R
C12 C 0.6562(5) 0.63527(16) 0.7204(5) 0.0397(10) Uani 1.000000 .
H12 H 0.6883(5) 0.63188(16) 0.6119(5) 0.0476(12) Uiso 1.000000 R
C13 C 0.4658(5) 0.63089(15) 0.6848(5) 0.0361(10) Uani 1.000000 .
C14 C 0.4014(5) 0.65282(16) 0.8334(6) 0.0419(11) Uani 1.000000 .
C15 C 0.4055(9) 0.6427(3) 1.1252(8) 0.087(2) Uani 1.000000 .
H15a H 0.2865(10) 0.646(2) 1.099(2) 0.130(3) Uiso 1.000000 GR
H15b H 0.440(6) 0.6183(10) 1.214(2) 0.130(3) Uiso 1.000000 GR
H15c H 0.457(6) 0.6744(10) 1.163(4) 0.130(3) Uiso 1.000000 GR
C16 C 0.7371(9) 0.5072(3) 0.9502(12) 0.105(3) Uani 1.000000 .
H16a H 0.659(5) 0.5120(18) 1.020(5) 0.158(5) Uiso 1.000000 GR
H16b H 0.733(8) 0.4729(3) 0.9126(12) 0.158(5) Uiso 1.000000 GR
H16c H 0.848(3) 0.5148(18) 1.016(5) 0.158(5) Uiso 1.000000 GR
C17 C 0.9389(6) 0.6017(2) 0.8612(8) 0.0650(15) Uani 1.000000 .
H17a H 0.9994(6) 0.5807(13) 0.952(4) 0.097(2) Uiso 1.000000 GR
H17b H 0.9639(10) 0.5918(16) 0.756(2) 0.097(2) Uiso 1.000000 GR
H17c H 0.9707(12) 0.6360(4) 0.886(6) 0.097(2) Uiso 1.000000 GR
C18 C -0.0652(6) 0.73816(18) 0.1460(7) 0.0510(12) Uani 1.000000 .
H18a H -0.0210(6) 0.73533(18) 0.0458(7) 0.0612(15) Uiso 1.000000 R
H18b H -0.0267(6) 0.76978(18) 0.2015(7) 0.0612(15) Uiso 1.000000 R
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03376 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
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
C1 O1 H1 109.5 . . ?
C13 O3 C5 116.8(3) . . ?
C9 O4 H4 109.5 . . ?
C12 O5 H5 109.5 . . ?
H6 H5 O5 161(4) 4_676 . ?
C18 O6 H6 109.5 . . ?
O6 H6 H5 169(3) . 4_475 ?
C15 O8 C14 117.4(4) . . ?
C2 C1 O1 117.9(4) . . ?
C6 C1 O1 121.4(4) . . ?
C6 C1 C2 120.7(4) . . ?
H2 C2 C1 120.1(3) . . ?
C3 C2 C1 119.9(4) . . ?
C3 C2 H2 120.1(3) . . ?
C4 C3 C2 120.7(4) . . ?
C18 C3 C2 121.6(4) . . ?
C18 C3 C4 117.6(4) . . ?
H4a C4 C3 120.5(2) . . ?
C5 C4 C3 118.9(4) . . ?
C5 C4 H4a 120.5(2) . . ?
C4 C5 O3 116.7(3) . . ?
C6 C5 O3 120.7(4) . . ?
C6 C5 C4 122.4(4) . . ?
C5 C6 C1 117.2(4) . . ?
C7 C6 C1 122.4(4) . . ?
C7 C6 C5 120.1(4) . . ?
C6 C7 O2 121.4(4) . . ?
C8 C7 O2 121.5(4) . . ?
C8 C7 C6 116.9(4) . . ?
C9 C8 C7 121.6(4) . . ?
C13 C8 C7 116.9(4) . . ?
C13 C8 C9 121.4(4) . . ?
C8 C9 O4 122.3(4) . . ?
C10 C9 O4 113.0(4) . . ?
C10 C9 C8 124.6(4) . . ?
H10 C10 C9 107.2(3) . . ?
C11 C10 C9 114.4(4) . . ?
C11 C10 H10 107.2(3) . . ?
C16 C10 C9 110.6(4) . . ?
C16 C10 H10 107.2(4) . . ?
C16 C10 C11 110.0(5) . . ?
H11 C11 C10 107.9(3) . . ?
C12 C11 C10 112.5(4) . . ?
C12 C11 H11 107.9(2) . . ?
C17 C11 C10 111.3(4) . . ?
C17 C11 H11 107.9(3) . . ?
C17 C11 C12 109.2(4) . . ?
C11 C12 O5 108.6(3) . . ?
H12 C12 O5 108.6(2) . . ?
H12 C12 C11 108.6(2) . . ?
C13 C12 O5 108.6(3) . . ?
C13 C12 C11 113.8(3) . . ?
C13 C12 H12 108.6(2) . . ?
C8 C13 O3 111.4(3) . . ?
C12 C13 O3 103.9(3) . . ?
C12 C13 C8 112.3(3) . . ?
C14 C13 O3 107.5(3) . . ?
C14 C13 C8 110.2(3) . . ?
C14 C13 C12 111.2(3) . . ?
O8 C14 O7 124.9(5) . . ?
C13 C14 O7 124.1(4) . . ?
C13 C14 O8 111.0(3) . . ?
H15a C15 O8 109.5 . . ?
H15b C15 O8 109.5 . . ?
H15b C15 H15a 109.5 . . ?
H15c C15 O8 109.5 . . ?
H15c C15 H15a 109.5 . . ?
H15c C15 H15b 109.5 . . ?
H16a C16 C10 109.5 . . ?
H16b C16 C10 109.5 . . ?
H16b C16 H16a 109.5 . . ?
H16c C16 C10 109.5 . . ?
H16c C16 H16a 109.5 . . ?
H16c C16 H16b 109.5 . . ?
H17a C17 C11 109.5 . . ?
H17b C17 C11 109.5 . . ?
H17b C17 H17a 109.5 . . ?
H17c C17 C11 109.5 . . ?
H17c C17 H17a 109.5 . . ?
H17c C17 H17b 109.5 . . ?
C3 C18 O6 113.8(4) . . ?
H18a C18 O6 108.8(3) . . ?
H18a C18 C3 108.8(3) . . ?
H18b C18 O6 108.8(2) . . ?
H18b C18 C3 108.8(2) . . ?
H18b C18 H18a 107.7 . . ?
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 0.8200 . ?
O1 C1 1.350(5) . ?
O2 C7 1.265(5) . ?
O3 C5 1.377(5) . ?
O3 C13 1.435(5) . ?
O4 H4 0.8200 . ?
O4 C9 1.330(5) . ?
O5 H5 0.8200 . ?
O5 C12 1.427(5) . ?
H5 H6 1.105(9) 4_676 ?
O6 H6 0.8200 . ?
O6 C18 1.429(6) . ?
O7 C14 1.189(6) . ?
O8 C14 1.312(6) . ?
O8 C15 1.451(6) . ?
C1 C2 1.380(6) . ?
C1 C6 1.417(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.391(6) . ?
C3 C4 1.385(6) . ?
C3 C18 1.508(6) . ?
C4 H4a 0.9300 . ?
C4 C5 1.379(6) . ?
C5 C6 1.400(6) . ?
C6 C7 1.447(6) . ?
C7 C8 1.441(6) . ?
C8 C9 1.364(6) . ?
C8 C13 1.498(5) . ?
C9 C10 1.502(6) . ?
C10 H10 0.9800 . ?
C10 C11 1.534(6) . ?
C10 C16 1.545(8) . ?
C11 H11 0.9800 . ?
C11 C12 1.527(6) . ?
C11 C17 1.542(6) . ?
C12 H12 0.9800 . ?
C12 C13 1.536(6) . ?
C13 C14 1.542(6) . ?
C15 H15a 0.9600 . ?
C15 H15b 0.9600 . ?
C15 H15c 0.9600 . ?
C16 H16a 0.9600 . ?
C16 H16b 0.9600 . ?
C16 H16c 0.9600 . ?
C17 H17a 0.9600 . ?
C17 H17b 0.9600 . ?
C17 H17c 0.9600 . ?
C18 H18a 0.9700 . ?
C18 H18b 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
O1 C1 C2 C3 -176.7(4) . . . . ?
O1 C1 C6 C5 -179.2(5) . . . . ?
O1 C1 C6 C7 6.6(6) . . . . ?
O2 C7 C6 C1 7.7(5) . . . . ?
O2 C7 C6 C5 -166.4(4) . . . . ?
O2 C7 C8 C9 8.9(5) . . . . ?
O2 C7 C8 C13 -170.3(4) . . . . ?
O3 C5 C4 C3 177.1(4) . . . . ?
O3 C5 C6 C1 -178.2(4) . . . . ?
O3 C5 C6 C7 -3.9(5) . . . . ?
O3 C13 C8 C7 -41.4(4) . . . . ?
O3 C13 C8 C9 139.4(4) . . . . ?
O3 C13 C12 O5 72.1(3) . . . . ?
O3 C13 C12 C11 -166.8(3) . . . . ?
O3 C13 C14 O7 3.2(4) . . . . ?
O3 C13 C14 O8 -178.5(3) . . . . ?
O4 C9 C8 C7 -3.2(6) . . . . ?
O4 C9 C8 C13 175.9(4) . . . . ?
O4 C9 C10 C11 -170.9(4) . . . . ?
O4 C9 C10 C16 -46.0(6) . . . . ?
O5 C12 C11 C10 173.1(4) . . . . ?
O5 C12 C11 C17 -62.8(4) . . . . ?
O5 C12 C13 C8 -167.3(3) . . . . ?
O5 C12 C13 C14 -43.3(4) . . . . ?
O6 C18 C3 C2 18.5(5) . . . . ?
O6 C18 C3 C4 -164.9(4) . . . . ?
O7 C14 O8 C15 -2.0(7) . . . . ?
O7 C14 C13 C8 -118.4(5) . . . . ?
O7 C14 C13 C12 116.4(5) . . . . ?
O8 C14 C13 C8 59.9(4) . . . . ?
O8 C14 C13 C12 -65.3(4) . . . . ?
C1 C2 C3 C4 -4.8(6) . . . . ?
C1 C2 C3 C18 171.8(4) . . . . ?
C1 C6 C5 C4 -3.7(5) . . . . ?
C1 C6 C7 C8 -177.0(4) . . . . ?
C2 C3 C4 C5 1.9(5) . . . . ?
C3 C4 C5 C6 2.4(5) . . . . ?
C4 C5 C6 C7 170.7(4) . . . . ?
C5 C6 C7 C8 9.0(5) . . . . ?
C6 C7 C8 C9 -166.5(4) . . . . ?
C6 C7 C8 C13 14.3(4) . . . . ?
C7 C8 C9 C10 174.7(4) . . . . ?
C7 C8 C13 C12 -157.5(4) . . . . ?
C7 C8 C13 C14 77.9(4) . . . . ?
C8 C9 C10 C11 11.1(5) . . . . ?
C8 C9 C10 C16 135.9(6) . . . . ?
C8 C13 C12 C11 -46.3(4) . . . . ?
C9 C10 C11 C12 -33.2(5) . . . . ?
C9 C10 C11 C17 -156.2(5) . . . . ?
C10 C11 C12 C13 52.0(4) . . . . ?
C11 C12 C13 C14 77.8(4) . . . . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.9980(5)
2 0.0020(5)
