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_1574663
_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 H18 O2'
_chemical_formula_sum            'C15 H18 O2'
_chemical_formula_weight         230.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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                 95.478(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4319(3)
_cell_length_b                   5.7056(2)
_cell_length_c                   23.0001(6)
_cell_measurement_reflns_used    24609
_cell_measurement_temperature    150
_cell_measurement_theta_max      28.87
_cell_measurement_theta_min      2.17
_cell_volume                     1232.09(7)
_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  (Sheldrick, 2015)'
_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 0.941
_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  0.0186
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            21331
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.909
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.226
_diffrn_reflns_theta_min         2.169
_diffrn_source                   Axo_Mo
_diffrn_source_current           1.00
_diffrn_source_power             0.050
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.081
_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    1.242
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             496
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 2188 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         6063
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0350
_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^)+(0.0681P)^2^+0.0193P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.0981
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.870
_reflns_number_gt                5444
_reflns_number_total             6063
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc02953h3.cif
_cod_data_source_block           jp389-1f1
_cod_depositor_comments
'Adding full bibliography for 1574658--1574665.cif.'
_cod_database_code               1574663
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00G(H00G), C00K(H00S)
2.b Secondary CH2 refined with riding coordinates:
 C00E(H00C,H00D), C00H(H00E,H00F), C00O(H00T,H00U), C00P(H00K,H00L), C00U(H00Y,
 H), C00W(H00,HB)
2.c X=CH2 refined with riding coordinates:
 C007(H00A,H00B), C00V(H00Z,HA)
2.d Idealised Me refined as rotating group:
 C00N(H00H,H00I,H00J), C00Q(H00M,H00N,H00O), C00R(H00V,H00W,H00X), C00T(H00P,
 H00Q,H00R), C00X(H1,HC,HD), C00Y(H2,HE,HF)
;
_shelx_res_checksum              25444
_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 90.7
_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 58.5
_stoe_evaluation_lana_max_2theta_desired 58.5
_stoe_evaluation_lana_mean_redundancy 3.5
_stoe_evaluation_lana_number_refls_after_or 21354
_stoe_evaluation_lana_number_refls_outliers 1279
_stoe_evaluation_lana_number_refls_total 22633
_stoe_evaluation_lana_number_refls_unique 6072
_stoe_evaluation_lana_number_refls_written 21354
_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 2
_stoe_evaluation_lana_table
;
2Theta           6.6   12.8   19.0   25.2   31.4   37.6   43.8   50.0   56.2
<Resolution>    5.07   3.08   2.17   1.61   1.31   1.10   0.95   0.84   0.77
N(total)         337   1037   1396   2255   3292   4010   4277   4376   1653
<Redundancy>     8.1    8.6    5.3    4.7    4.5    4.0    3.4    2.8    1.7
Complet. [%%]   100.0  100.0  100.0   99.8  100.0  100.0  100.0   99.7   60.7
<I/sigma>      264.7  203.9  106.5   61.3   34.7   24.3   11.7    6.4    5.0
R(int)         0.015  0.013  0.015  0.016  0.019  0.023  0.036  0.061  0.079
;
_stoe_measurement_identifier     JP389-1F1
_stoe_measurement_max_exposure_per_frame '60.0 s'
_stoe_measurement_mean_exposure_per_frame '60.0 s'
_stoe_measurement_min_exposure_per_frame '60.0 s'
_stoe_measurement_total_exposure_time '17.7 h'
_stoe_measurement_total_frame_number 1061
_stoe_measurement_total_run_number 19
_stoe_measurement_tube_power     '50.0 W'