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_7159336
_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      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             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                 108.143(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6389(2)
_cell_length_b                   11.9203(2)
_cell_length_c                   12.9914(3)
_cell_measurement_reflns_used    7769
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.6950
_cell_measurement_theta_min      3.6820
_cell_volume                     1859.97(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      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.976
_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    --  -41.11 125.00  90.00   94
  2  \w   -115.00 -17.00   1.00    1.00    --  -41.11 -38.00 -30.00   98
  3  \w      9.00 117.00   1.00    1.00    --   41.11  77.00  90.00  108
  4  \w     17.00 115.00   1.00    1.00    --   41.11  38.00 -90.00   98
  5  \w      1.00  82.00   1.00    1.00    --   41.11 -99.00 -30.00   81
  6  \w     31.00 136.00   1.00    1.85    --  107.58 -30.00 150.00  105
  7  \w     34.00 122.00   1.00    1.85    --  107.58-125.00 -30.00   88
  8  \w     31.00 136.00   1.00    1.85    --  107.58 -30.00 -30.00  105
  9  \w     82.00 178.00   1.00    1.85    --  107.58  45.00 -30.00   96
 10  \w     82.00 178.00   1.00    1.85    --  107.58  45.00 150.00   96
 11  \w     79.00 178.00   1.00    1.85    --  107.58  30.00-150.00   99
 12  \w     25.00 110.00   1.00    1.85    --  107.58 -95.00  90.00   85
 13  \w     25.00  89.00   1.00    1.85    --  107.58 -95.00  30.00   64
;
_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      -0.0776191000
_diffrn_orient_matrix_UB_12      0.1028371000
_diffrn_orient_matrix_UB_13      -0.0196110000
_diffrn_orient_matrix_UB_21      -0.1012750000
_diffrn_orient_matrix_UB_22      -0.0767604000
_diffrn_orient_matrix_UB_23      -0.0489885000
_diffrn_orient_matrix_UB_31      -0.0132447000
_diffrn_orient_matrix_UB_32      -0.0154012000
_diffrn_orient_matrix_UB_33      0.1130608000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12983
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.801
_diffrn_reflns_theta_min         3.680
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.671
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65336
_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    1.230
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3674
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0400
_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^)+(0.0510P)^2^+0.6239P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1055
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3298
_reflns_number_total             3674
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00426k2.cif
_cod_data_source_block           c70m-2-4-1
_cod_depositor_comments
'Adding full bibliography for 7159333--7159336.cif.'
_cod_original_cell_volume        1859.97(7)
_cod_database_code               7159336
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.930
_shelx_estimated_absorpt_t_min   0.912
_reflns_odcompleteness_completeness 99.54
_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(H4A,H4B), C4'(H4'A,H4'B)
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), C11'(H11A,H11B,H11C), C11(H11D,
 H11E,H11F), C10(H10D,H10E,H10F)
;
_shelx_res_checksum              53788
_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 1.411
_oxdiff_exptl_absorpt_empirical_full_min 0.403