Biomimetic synthesis of <i>Sinularia</i> meroterpenoids and photochemical reactivity of capillobenzopyranol.
French, Sarah A.; Peralta, Ricardo A.; George, Jonathan H.; Organic & biomolecular chemistry 23 (2025) 10766–10770; doi:10.1039/d5ob01430a

data_7160865
_publ_section_title
;
 Biomimetic synthesis of <i>Sinularia</i> meroterpenoids and photochemical
 reactivity of capillobenzopyranol.
;
_journal_issue                   47
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              10766
_journal_page_last               10770
_journal_paper_doi               10.1039/d5ob01430a
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C22 H26 O3'
_chemical_formula_sum            'C22 H26 O3'
_chemical_formula_weight         338.43
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2025-09-05
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2025-09-05 deposited with the CCDC.	2025-10-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.935(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6017(8)
_cell_length_b                   13.7639(6)
_cell_length_c                   12.7600(8)
_cell_measurement_reflns_used    11370
_cell_measurement_temperature    150.00(14)
_cell_measurement_theta_max      28.5150
_cell_measurement_theta_min      3.7860
_cell_volume                     1847.6(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1695
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     -7.00  91.00   1.00   15.00    --   19.03  37.00-120.00   98
  2  \w     -2.00  88.00   1.00   15.00    --   19.03  57.00  30.00   90
  3  \w      1.00  80.00   1.00   15.00    --   19.03-131.00  99.28   79
  4  \w     -2.00  88.00   1.00   15.00    --   19.03  57.00 120.00   90
  5  \w     -7.00  91.00   1.00   15.00    --   19.03  37.00 -30.00   98
  6  \w    -50.00  40.00   1.00   15.00    --   19.03 -57.00 120.00   90
  7  \w    -40.00  49.00   1.00   15.00    --  -19.65  57.00 -30.00   89
  8  \w    -25.00  22.00   1.00   15.00    --  -19.65 -99.00-150.00   47
  9  \w    -50.00  50.00   1.00   15.00    --  -19.65  77.00-150.00  100
 10  \w    -54.00  92.00   1.00   15.00    --   19.03   0.00-180.00  146
 11  \w    -54.00  92.00   1.00   15.00    --   19.03   0.00-150.00  146
 12  \w    -90.00 -10.00   1.00   15.00    --  -19.65 146.00 118.98   80
 13  \w    -25.00  22.00   1.00   15.00    --  -19.65 -99.00 150.00   47
 14  \w    -96.00 -32.00   1.00   15.00    --  -19.65 178.00  30.00   64
 15  \w    -25.00  22.00   1.00   15.00    --  -19.65 -99.00 -90.00   47
 16  \w    -81.00  -1.00   1.00   15.00    --  -19.65 131.00 -89.05   80
 17  \w    -54.00  92.00   1.00   15.00    --   19.03   0.00 -90.00  146
 18  \w    -54.00  92.00   1.00   15.00    --   19.03   0.00 -60.00  146
 19  \w    -54.00  92.00   1.00   15.00    --   19.03   0.00 -30.00  146
 20  \w    -54.00  92.00   1.00   15.00    --   19.03   0.00   0.00  146
 21  \w    -54.00  -5.00   1.00   15.00    --   19.03   0.00  30.00   49
 22  \w    -54.00  92.00   1.00   15.00    --   19.03   0.00-120.00  146
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0661978000
_diffrn_orient_matrix_UB_12      0.0008571000
_diffrn_orient_matrix_UB_13      0.0357129000
_diffrn_orient_matrix_UB_21      0.0098805000
_diffrn_orient_matrix_UB_22      -0.0353398000
_diffrn_orient_matrix_UB_23      -0.0358849000
_diffrn_orient_matrix_UB_31      0.0077873000
_diffrn_orient_matrix_UB_32      0.0375259000
_diffrn_orient_matrix_UB_33      -0.0345699000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0846
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            80523
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.371
_diffrn_reflns_theta_min         3.444
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44030
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.051
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         4806
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0518
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1408
_refine_ls_wR_factor_ref         0.1586
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3528
_reflns_number_total             4806
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01430a2.cif
_cod_data_source_block           p21c
_cod_depositor_comments          'Adding full bibliography for 7160865.cif.'
_cod_database_code               7160865
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C25H25O4
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.977
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C009(H009), C00D(H00D), C00E(H00E)
1.b Secondary CH2 refined with riding coordinates:
 C00L(H00L,H00M), C00M(H00N,H00O), C00N(H00P,H00Q)
1.c Aromatic/amide H refined with riding coordinates:
 C007(H007), C00A(H00A), C00F(H00F), C00H(H00H)
1.d Idealised Me refined as rotating group:
 C00J(H00B,H00C,H00G), C00K(H00I,H00J,H00K), C00O(H00R,H00S,H00T), C00P(H00U,
 H00V,H00W)
1.e Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_shelx_res_checksum              23853
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.364
_oxdiff_exptl_absorpt_empirical_full_min 0.426