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_7159333
_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         'C21 H28 O4'
_chemical_formula_sum            'C21 H28 O4'
_chemical_formula_weight         344.43
_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     iterative
_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
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.95724(19)
_cell_length_b                   9.43219(18)
_cell_length_c                   22.4623(4)
_cell_measurement_reflns_used    11072
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      74.1050
_cell_measurement_theta_min      3.8880
_cell_volume                     1897.76(6)
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(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 0.987
_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    -73.00  35.00   1.00    1.00    --  -40.73  77.00  60.00  108
  2  \w   -115.00 -16.00   1.00    1.00    --  -40.73 -38.00 150.00   99
  3  \w    -34.00  65.00   1.00    1.00    --   40.73 -38.00   0.00   99
  4  \w     79.00 178.00   1.00    1.92    --  108.20  61.00-120.00   99
  5  \w     79.00 178.00   1.00    1.92    --  108.20  61.00   0.00   99
  6  \w    101.00 178.00   1.00    1.92    --  108.20  95.00 100.00   77
  7  \w     26.00 109.00   1.00    1.92    --  108.20 -94.00 120.00   83
  8  \w     82.00 178.00   1.00    1.92    --  108.20  45.00 -30.00   96
  9  \w     76.00 178.00   1.00    1.92    --  108.20  77.00 150.00  102
 10  \w   -113.00 -13.00   1.00    1.00    --  -40.73 -57.00  60.00  100
 11  \w   -113.00 -13.00   1.00    1.00    --  -40.73 -57.00 -60.00  100
 12  \w      1.00  82.00   1.00    1.00    --   40.73 -99.00 -90.00   81
 13  \w     94.00 178.00   1.00    1.92    --  108.20 125.00-180.00   84
 14  \w     76.00 178.00   1.00    1.92    --  108.20  77.00  60.00  102
 15  \w   -117.00  -8.00   1.00    1.00    --  -40.98 -77.00 -60.00  109
 16  \w   -117.00  -8.00   1.00    1.00    --  -40.98 -77.00  30.00  109
 17  \w    -69.00  32.00   1.00    1.00    --  -40.98  57.00-150.00  101
 18  \w    -66.00   9.00   1.00    1.00    --  -40.98  38.00 -30.00   75
;
_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      -0.0825706000
_diffrn_orient_matrix_UB_12      0.1078311000
_diffrn_orient_matrix_UB_13      -0.0396043000
_diffrn_orient_matrix_UB_21      0.1259761000
_diffrn_orient_matrix_UB_22      0.1084861000
_diffrn_orient_matrix_UB_23      0.0102530000
_diffrn_orient_matrix_UB_31      0.0829605000
_diffrn_orient_matrix_UB_32      -0.0573718000
_diffrn_orient_matrix_UB_33      -0.0550437000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            16860
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.145
_diffrn_reflns_theta_min         3.936
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.658
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31720
_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    1.206
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1311 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3766
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0388
_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^)+(0.0532P)^2^+0.2744P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1030
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                3421
_reflns_number_total             3766
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00426k2.cif
_cod_data_source_block           c_70m_3_2
_cod_depositor_comments
'Adding full bibliography for 7159333--7159336.cif.'
_cod_original_cell_volume        1897.76(7)
_cod_database_code               7159333
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 100.00
_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), C6'(H6'), C5(H5), C5'(H5')
2.b Secondary CH2 refined with riding coordinates:
 C7'(H7'A,H7'B), C7(H7A,H7B), C4'(H4'A,H4'B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C10'(H10A,H10B,H10C), C10(H10D,H10E,H10F), C11'(H11A,
 H11B,H11C), C11(H11D,H11E,H11F)
;
_shelx_res_checksum              90144
_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 3.147
_oxdiff_exptl_absorpt_empirical_full_min 0.672