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_1574665
_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         'C15 H16 O3'
_chemical_formula_sum            'C15 H16 O3'
_chemical_formula_weight         244.28
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2025-03-03
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-03-04 deposited with the CCDC.	2025-05-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8918(3)
_cell_length_b                   10.0340(4)
_cell_length_c                   13.7443(6)
_cell_measurement_reflns_used    16255
_cell_measurement_temperature    150
_cell_measurement_theta_max      29.04
_cell_measurement_theta_min      2.51
_cell_volume                     1226.27(8)
_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_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 0.998
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_details
;
 682 frames, detector distance = 60 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  0.0194
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13303
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.044
_diffrn_reflns_theta_min         2.513
_diffrn_source                   Axo_Mo
_diffrn_source_power             0.050
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  1.0000
_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    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.5(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         3002
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0355
_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^)+(0.0704P)^2^+0.0052P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.0988
_reflns_Friedel_coverage         0.685
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.878
_reflns_number_gt                2765
_reflns_number_total             3002
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc02953h3.cif
_cod_data_source_block           jp472-2-f1
_cod_depositor_comments
'Adding full bibliography for 1574658--1574665.cif.'
_cod_database_code               1574665
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5(12)
 0.5(12)
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
3.a Ternary CH refined with riding coordinates:
 C00E(H00E)
3.b Secondary CH2 refined with riding coordinates:
 C007(H00A,H00B), C009(H00C,H00D), C00F(H00F,H00G)
3.c Idealised Me refined as rotating group:
 C00G(H00H,H00I,H00J), C00H(H00K,H00L,H00M), C00I(H00N,H00O,H00P)
;
_shelx_res_checksum              45472
_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 91.9
_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 58.1
_stoe_evaluation_lana_max_2theta_desired 58.1
_stoe_evaluation_lana_mean_redundancy 4.4
_stoe_evaluation_lana_number_refls_after_or 13357
_stoe_evaluation_lana_number_refls_outliers 808
_stoe_evaluation_lana_number_refls_total 14165
_stoe_evaluation_lana_number_refls_unique 3021
_stoe_evaluation_lana_number_refls_written 13357
_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 222
_stoe_evaluation_lana_table
;
2Theta           6.5   12.7   18.9   25.1   31.3   37.5   43.7   49.9   56.1
<Resolution>    5.44   3.15   2.17   1.62   1.31   1.10   0.95   0.84   0.78
N(total)         155    686    909   1421   2095   2571   2618   2754    956
<Redundancy>     8.7   10.0    6.7    6.2    5.9    5.2    4.2    3.5    2.0
Complet. [%%]   100.0  100.0  100.0  100.0   99.7   99.8  100.0   99.5   63.8
<I/sigma>      351.3  184.0  117.7   68.2   36.7   27.3   11.6    6.9    5.8
R(int)         0.018  0.016  0.016  0.017  0.021  0.022  0.036  0.057  0.062
;
_stoe_measurement_identifier     JP472-2-F1
_stoe_measurement_max_exposure_per_frame '30.0 s'
_stoe_measurement_mean_exposure_per_frame '30.0 s'
_stoe_measurement_min_exposure_per_frame '30.0 s'
_stoe_measurement_total_exposure_time '5.7 h'
_stoe_measurement_total_frame_number 682
_stoe_measurement_total_run_number 15
_stoe_measurement_tube_power     '50.0 W'