Isolation of new compounds related to xyloketals biosynthesis implies an alternative pathway for furan-fused-chromene formation.
Huang, Jia-Hua; Lv, Jian-Ming; Xie, Yan-Feng; Zhao, Huan; Xiao, Liang-Yan; Dai, Ping; Qin, Sheng-Ying; Hu, Dan; Gao, Hao; Yao, Xin-Sheng; Organic & biomolecular chemistry 21 (2023) 4309–4318; doi:10.1039/d3ob00426k

data_7159335
_publ_section_title
;
 Isolation of new compounds related to xyloketals biosynthesis implies an
 alternative pathway for furan-fused-chromene formation.
;
_journal_issue                   20
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4309
_journal_page_last               4318
_journal_paper_doi               10.1039/d3ob00426k
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C15 H20 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     direct
_audit_creation_date             2023-03-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-03-04 deposited with the CCDC.	2023-05-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.5004(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.35263(13)
_cell_length_b                   15.2684(2)
_cell_length_c                   9.55302(17)
_cell_measurement_reflns_used    12380
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.4390
_cell_measurement_theta_min      2.8480
_cell_volume                     1364.12(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_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    -96.00  -2.00   1.00    1.00    --  -40.73 125.00  30.00   94
  2  \w    -69.00  32.00   1.00    1.00    --  -40.73  57.00 -60.00  101
  3  \w     94.00 178.00   1.00    1.00    --  106.95 125.00-180.00   84
  4  \w     94.00 178.00   1.00    1.00    --  106.95 125.00  60.00   84
  5  \w     81.00 178.00   1.00    1.00    --  106.95  45.00-180.00   97
  6  \w     31.00 140.00   1.00    1.00    --  106.95 -77.00   0.00  109
  7  \w     74.00 178.00   1.00    1.00    --  106.95  77.00 120.00  104
  8  \w   -113.00 -13.00   1.00    1.00    --  -40.73 -57.00 -30.00  100
  9  \w   -113.00 -13.00   1.00    1.00    --  -40.73 -57.00-150.00  100
 10  \w     81.00 178.00   1.00    1.00    --  106.95  45.00 -30.00   97
 11  \w     81.00 178.00   1.00    1.00    --  106.95  45.00 -90.00   97
 12  \w     25.00 109.00   1.00    1.00    --  106.95 -95.00-180.00   84
 13  \w     78.00 178.00   1.00    1.00    --  106.95  61.00  30.00  100
 14  \w   -113.00 -13.00   1.00    1.00    --  -40.73 -57.00  90.00  100
 15  \w   -117.00  -8.00   1.00    1.00    --  -40.73 -77.00-180.00  109
 16  \w     81.00 178.00   1.00    1.00    --  106.95  45.00  90.00   97
 17  \w     78.00 178.00   1.00    1.00    --  106.95  61.00   0.00  100
 18  \w     74.00 178.00   1.00    1.00    --  106.95  77.00 -90.00  104
 19  \w     74.00 178.00   1.00    1.00    --  106.95  77.00-150.00  104
 20  \w    -65.00  34.00   1.00    1.00    --  -40.73  38.00-120.00   99
 21  \w   -117.00  -8.00   1.00    1.00    --  -40.73 -77.00 -60.00  109
 22  \w     34.00  73.00   1.00    1.00    --  106.95-125.00 -60.00   39
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1139022000
_diffrn_orient_matrix_UB_12      -0.0543334000
_diffrn_orient_matrix_UB_13      0.0767941000
_diffrn_orient_matrix_UB_21      -0.1188077000
_diffrn_orient_matrix_UB_22      0.0568719000
_diffrn_orient_matrix_UB_23      -0.0660609000
_diffrn_orient_matrix_UB_31      -0.0090154000
_diffrn_orient_matrix_UB_32      -0.0631484000
_diffrn_orient_matrix_UB_33      -0.1254146000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            16884
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.988
_diffrn_reflns_theta_min         4.629
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.667
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 2345 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         5393
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0378
_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^)+(0.0588P)^2^+0.0810P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.0972
_reflns_Friedel_coverage         0.896
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.955
_reflns_number_gt                5216
_reflns_number_total             5393
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00426k2.cif
_cod_data_source_block           ahk-4
_cod_depositor_comments
;
Adding full bibliography for 7159333--7159336.cif.

2024-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C30 H40 O6'
_cod_original_formula_weight         496.62
_cod_original_formula_moiety         '2(C15 H20 O3)'
_cod_original_formula_units_Z            2
_cod_database_code               7159335
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.930
_shelx_estimated_absorpt_t_min   0.901
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C6'(H6'), C5'(H5'), C6(H6), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C7'(H7'A,H7'B), C4'(H4'A,H4'B), C7(H7A,H7B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C13'(H13'), C15'(H15'), C15(H15), C13(H13)
2.d Idealised Me refined as rotating group:
 C16'(H16A,H16B,H16C), C10'(H10A,H10B,H10C), C11'(H11A,H11B,H11C), C17'(H17A,
 H17B,H17C), C16(H16D,H16E,H16F), C17(H17D,H17E,H17F), C10(H10D,H10E,H10F),
 C11(H11D,H11E,H11F)
;
_shelx_res_checksum              82141
_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 4.016
_oxdiff_exptl_absorpt_empirical_full_min 0.647