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_1574659
_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 O3'
_chemical_formula_sum            'C15 H20 O3'
_chemical_formula_weight         248.31
_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             2025-02-11
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-02-11 deposited with the CCDC.	2025-05-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.972(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2282(8)
_cell_length_b                   14.1294(13)
_cell_length_c                   13.1197(16)
_cell_measurement_reflns_used    8151
_cell_measurement_temperature    150
_cell_measurement_theta_max      28.03
_cell_measurement_theta_min      2.82
_cell_volume                     1339.7(3)
_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 2.5.18.0 (STOE, 2024)
X-Area LANA 2.8.4 (STOE, 2024)
;
_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 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
 517 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  0.1143
_diffrn_reflns_av_unetI/netI     0.1038
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8893
_diffrn_reflns_point_group_measured_fraction_full 0.930
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        25.026
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         2.818
_diffrn_source                   Axo_Mo
_diffrn_source_current           1.00
_diffrn_source_power             0.050
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.084
_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    1.231
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             536
_refine_diff_density_max         0.783
_refine_diff_density_min         -0.649
_refine_diff_density_rms         0.148
_refine_ls_abs_structure_details
;
 Flack x determined using 942 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   5.4(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.169
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         4410
_refine_ls_number_restraints     811
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.1498
_refine_ls_R_factor_gt           0.1276
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3007
_refine_ls_wR_factor_ref         0.3180
_reflns_Friedel_coverage         0.799
_reflns_Friedel_fraction_full    0.864
_reflns_Friedel_fraction_max     0.864
_reflns_number_gt                3133
_reflns_number_total             4410
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc02953h3.cif
_cod_data_source_block           jp444-2-f1
_cod_depositor_comments
'Adding full bibliography for 1574658--1574665.cif.'
_cod_database_code               1574659
_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, All O(H) groups
2. Uiso/Uaniso restraints and constraints
O005 \\sim O002 \\sim C007 \\sim C008 \\sim C00C \\sim C009 \\sim C00K \\sim
C00F \\sim C00A \\sim C00D \\sim C00G \\sim O003 \\sim C00E \\sim C00B \\sim
C00P \\sim C00Q \\sim C00X \\sim C00W: within 3A with sigma of 0.002 and sigma
for terminal atoms of 0.004 within 3A
C00Z \\sim O001 \\sim C00J \\sim C00M \\sim C00N \\sim C00H \\sim C00I \\sim
C00Y \\sim C00L \\sim C00T \\sim C00R \\sim C00U \\sim C00S \\sim C00V \\sim
C00O \\sim O006 \\sim C010 \\sim O004: within 3A with sigma of 0.002 and sigma
for terminal atoms of 0.004 within 3A
3.a Ternary CH refined with riding coordinates:
 C00A(H00N), C00E(H00Q), C00J(H00J), C00P(H00X), C00S(H00S), C00Z(H00Z)
3.b Secondary CH2 refined with riding coordinates:
 C00C(H00O,H00P), C00G(H00R,H00T), C00L(H00A,H00B), C00N(H00C,H00D), C00U(H00H,
 H00I), C00X(H1,HD)
3.c Idealised Me refined as rotating group:
 C00K(H00U,H00V,H00W), C00Q(H00Y,H,HA), C00T(H00E,H00F,H00G), C00W(H00,HB,HC),
 C00Y(H00K,H00L,H00M), C010(H01A,H01B,H01C)
3.d Idealised tetrahedral OH refined as rotating group:
 O001(H001), O003(H003), O005(H005), O006(H006)
;
_shelx_res_checksum              81212
_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   12.7
_stoe_evaluation_integration_b   0.9
_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 90.4
_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 55.0
_stoe_evaluation_lana_mean_redundancy 1.9
_stoe_evaluation_lana_number_refls_after_or 10805
_stoe_evaluation_lana_number_refls_outliers 925
_stoe_evaluation_lana_number_refls_total 11730
_stoe_evaluation_lana_number_refls_unique 5594
_stoe_evaluation_lana_number_refls_written 10805
_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           7.9   13.5   19.1   24.7   30.3   35.9   41.5   47.1   52.7
<Resolution>    5.00   3.06   2.18   1.65   1.35   1.15   1.00   0.89   0.81
N(total)         202    533    612    854   1393   1705   2121   2312   1998
<Redundancy>     3.4    3.3    2.4    2.1    2.1    2.0    2.0    1.8    1.6
Complet. [%%]   100.0   99.2   91.1   88.0   94.5   94.0   93.8   92.1   82.2
<I/sigma>      211.4   83.5   62.6   29.4   14.3   10.4    4.3    2.0    1.3
R(int)         0.062  0.115  0.108  0.138  0.155  0.153  0.165  0.228  0.295
;
_stoe_measurement_identifier     JP444-2-F1
_stoe_measurement_max_exposure_per_frame '130.0 s'
_stoe_measurement_mean_exposure_per_frame '130.0 s'
_stoe_measurement_min_exposure_per_frame '130.0 s'
_stoe_measurement_total_exposure_time '18.7 h'
_stoe_measurement_total_frame_number 517
_stoe_measurement_total_run_number 10
_stoe_measurement_tube_power     '50.0 W'