Bio-inspired total synthesis of daphnepapytone A
Pereira, Joan; Casaretto, Nicolas; Frison, Gilles; Nay, Bastien; Chemical Science 16 (2025) 11375–11380; doi:10.1039/D5SC02953H

data_1574661
_publ_section_title
;
 Bio-inspired total synthesis of daphnepapytone A
;
_journal_issue                   25
_journal_name_full               'Chemical Science'
_journal_page_first              11375
_journal_page_last               11380
_journal_paper_doi               10.1039/D5SC02953H
_journal_volume                  16
_journal_year                    2025
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C70 H116 O4 Tm2'
_chemical_formula_sum            'C15 H18 O3'
_chemical_formula_weight         246.29
_space_group_crystal_system      trigonal
_space_group_IT_number           145
_space_group_name_Hall           'P 32'
_space_group_name_H-M_alt        'P 32'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-10-31
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-01-21 deposited with the CCDC.	2025-05-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   7.6126(5)
_cell_length_b                   7.6126(5)
_cell_length_c                   18.9125(15)
_cell_measurement_reflns_used    24609
_cell_measurement_temperature    150
_cell_measurement_theta_max      28.87
_cell_measurement_theta_min      3.09
_cell_volume                     949.17(12)
_computing_cell_refinement
;
X-Area Recipe 2.0.2 (STOE, 2024)
;
_computing_data_collection
;
X-Area Pilatus3_SV 1.31.194.0 (STOE, 2023)
;
_computing_data_reduction
;
X-Area Integrate 2.5.3.0 (STOE, 2021)
X-Area LANA 2.7.5.0 (STOE, 2022)
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 2.4, Darmstadt 2024
;
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'EIGER2 1M CDTE'
_diffrn_detector_area_resol_mean 13.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details      '304 frames, detector distance = 70 mm'
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, \w scans'
_diffrn_radiation_collimation    '1.2 0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16816
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.158
_diffrn_reflns_theta_min         3.090
_diffrn_source                   Axo_Mo
_diffrn_source_current           1.00
_diffrn_source_power             0.050
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  1.0000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
STOE LANA, absorption correction by scaling of reflection intensities.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(\m~2~-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             396
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1131 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         3196
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0335
_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/[\s^2^(Fo^2^)+(0.0434P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0718
_refine_ls_wR_factor_ref         0.0727
_reflns_Friedel_coverage         0.943
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.904
_reflns_number_gt                2667
_reflns_number_total             3196
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc02953h3.cif
_cod_data_source_block           jp382-1f1
_cod_depositor_comments
'Adding full bibliography for 1574658--1574665.cif.'
_cod_original_cell_volume        949.17(15)
_cod_database_code               1574661
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Sof(H00L)=Sof(H00M)=Sof(H00N)=1-FVAR(1)
 Sof(H00I)=Sof(H00J)=Sof(H00K)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C00B(H00C), C00D(H00D)
3.b Secondary CH2 refined with riding coordinates:
 C009(H00A,H00B), C00E(H00E,H00F), C00F(H00G,H00H)
3.c Disordered Me refined as rotating group:
 C00G(H00I,H00J,H00K,H00L,H00M,H00N)
3.d Idealised Me refined as rotating group:
 C00H(H00O,H00P,H00Q), C00I(H00R,H00S,H00T)
3.e Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_shelx_res_checksum              80132
_olex2_submission_special_instructions 'No special instructions were received'
_stoe_detector_distance          '60.0 mm'
_stoe_detector_pixelsize_x       '0.075 mm'
_stoe_detector_pixelsize_y       '0.075 mm'
_stoe_detector_size_x            '8.0 cm'
_stoe_detector_size_y            '7.7 cm'
_stoe_evaluation_integration_a   10.1
_stoe_evaluation_integration_b   0.1
_stoe_evaluation_integration_ems 0.011
_stoe_evaluation_lana_bis_l_even_max -
_stoe_evaluation_lana_bis_l_odd_max -
_stoe_evaluation_lana_bos_l_even_max 4
_stoe_evaluation_lana_bos_l_odd_max 1
_stoe_evaluation_lana_completeness 93.2
_stoe_evaluation_lana_dxs_max_order 3
_stoe_evaluation_lana_dys_max_order 3
_stoe_evaluation_lana_fs_max_order 3
_stoe_evaluation_lana_max_2theta_available 58.4
_stoe_evaluation_lana_max_2theta_desired 58.4
_stoe_evaluation_lana_mean_redundancy 5.2
_stoe_evaluation_lana_number_refls_after_or 16882
_stoe_evaluation_lana_number_refls_outliers 625
_stoe_evaluation_lana_number_refls_total 17507
_stoe_evaluation_lana_number_refls_unique 3225
_stoe_evaluation_lana_number_refls_written 16882
_stoe_evaluation_lana_or_c1      0.050
_stoe_evaluation_lana_or_c2      0
_stoe_evaluation_lana_or_c3      0
_stoe_evaluation_lana_or_c4      1.0
_stoe_evaluation_lana_point_group 3
_stoe_evaluation_lana_table
;
2Theta           8.3   14.3   20.3   26.3   32.3   38.3   44.3   50.3   56.3
<Resolution>    4.64   2.82   2.01   1.53   1.26   1.08   0.94   0.84   0.77
N(total)         384    918    944   1667   2359   2849   3527   3564   1295
<Redundancy>    11.6   10.4    5.8    6.4    6.3    6.2    5.5    4.6    2.5
Complet. [%%]   100.0  100.0  100.0   99.6  100.0  100.0  100.0  100.0   68.9
<I/sigma>      122.8   74.5   50.7   25.1   15.8   10.2    4.6    3.0    2.3
R(int)         0.017  0.017  0.019  0.025  0.031  0.042  0.079  0.106  0.118
;
_stoe_measurement_identifier     JP382-1F1
_stoe_measurement_max_exposure_per_frame '15.0 s'
_stoe_measurement_mean_exposure_per_frame '15.0 s'
_stoe_measurement_min_exposure_per_frame '15.0 s'
_stoe_measurement_total_exposure_time '4.3 h'
_stoe_measurement_total_frame_number 1036
_stoe_measurement_total_run_number 17
_stoe_measurement_tube_power     '50.0 W'