Synthesis of the ABC ring system of kadlongilactones.
Li, Liang; Li, Pengfei; Li, Tianhao; Zhang, Mingxiao; Liu, Wenjie; Li, Jing; Wang, Liang; Chen, Yue; Organic & biomolecular chemistry 21 (2023) 1704–1708; doi:10.1039/d2ob01701f

data_7159130
_publ_section_title
;
 Synthesis of the ABC ring system of kadlongilactones.
;
_journal_issue                   8
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1704
_journal_page_last               1708
_journal_paper_doi               10.1039/d2ob01701f
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C13 H20 O3'
_chemical_formula_sum            'C13 H20 O3'
_chemical_formula_weight         224.29
_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             2020-01-02
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2022-05-30 deposited with the CCDC.	2023-01-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.364(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.4722(5)
_cell_length_b                   12.8218(9)
_cell_length_c                   8.8354(9)
_cell_measurement_reflns_used    1822
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.0980
_cell_measurement_theta_min      5.1990
_cell_volume                     597.77(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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    -39.00  -3.00   1.00    1.00    --    0.00  82.00-150.00   36
  2  \w    -53.00 -25.00   1.00    1.00    --    0.00 -38.00  30.00   28
  3  \w     -4.00  44.00   1.00    1.00    --    0.00 -38.00  30.00   48
  4  \w     -1.00  89.00   1.00    1.00    --    0.00  82.00-150.00   90
  5  \w    158.00 184.00   1.00    1.50    --   98.20  61.00  60.00   26
  6  \w     63.00 130.00   1.00    1.50    --   98.20  61.00-180.00   67
  7  \w     68.00  94.00   1.00    1.50    --   98.20  61.00-150.00   26
  8  \w     62.00 145.00   1.00    1.50    --   98.20  61.00  60.00   83
  9  \w     66.00 135.00   1.00    1.50    --   98.20 -45.00   0.00   69
 10  \w     62.00 188.00   1.00    1.50    --   98.20  61.00  90.00  126
 11  \w     67.00 177.00   1.00    1.50    --   98.20  61.00-120.00  110
 12  \w     76.00 112.00   1.00    1.50    --   98.20  61.00  30.00   36
 13  \w    115.00 182.00   1.00    1.50    --   98.20  61.00  30.00   67
 14  \w      9.00  44.00   1.00    1.50    --   98.20 -45.00   0.00   35
 15  \w    139.00 179.00   1.00    1.50    --   98.20  61.00-180.00   40
 16  \w     98.00 178.00   1.00    1.50    --   98.20  61.00-150.00   80
 17  \w     99.00 188.00   1.00    1.50    --   98.20  61.00 120.00   89
 18  \w     66.00  92.00   1.00    1.50    --   98.20  61.00 120.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0969413000
_diffrn_orient_matrix_UB_12      -0.0317545000
_diffrn_orient_matrix_UB_13      -0.1737029000
_diffrn_orient_matrix_UB_21      -0.1387443000
_diffrn_orient_matrix_UB_22      -0.0939260000
_diffrn_orient_matrix_UB_23      0.0472714000
_diffrn_orient_matrix_UB_31      -0.2382311000
_diffrn_orient_matrix_UB_32      0.0678554000
_diffrn_orient_matrix_UB_33      -0.0157817000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_unetI/netI     0.0639
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3938
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        66.996
_diffrn_reflns_theta_max         66.995
_diffrn_reflns_theta_min         5.192
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_exptl_absorpt_coefficient_mu    0.701
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66191
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_description       plate
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.656
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.117
_refine_ls_abs_structure_details
;
 Flack x determined using 803 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2081
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0767
_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^)+(0.1498P)^2^+0.1373P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2031
_refine_ls_wR_factor_ref         0.2065
_reflns_Friedel_coverage         0.863
_reflns_Friedel_fraction_full    0.946
_reflns_Friedel_fraction_max     0.946
_reflns_number_gt                1924
_reflns_number_total             2081
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01701f2.cif
_cod_data_source_block           lwj-1-54
_cod_depositor_comments
'Adding full bibliography for 7159130--7159137.cif.'
_cod_original_cell_volume        597.76(10)
_cod_database_code               7159130
_reflns_odcompleteness_completeness 99.56
_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:
 C5(H5), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C2(H2A,H2B), C3(H3A,H3B), C12(H12A,H12B), C13(H13A,H13B),
 C11(H11A,H11B)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
;
_shelx_res_checksum              2695
_shelx_shelxl_version_number     2017/1
_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 1.463
_oxdiff_exptl_absorpt_empirical_full_min 0.746