Hypocretenolides: collective total syntheses and activities toward metastatic colon cancer.
Chen, Bolin; Zhang, Xijing; Yang, Yufen; Xu, Dongdong; Wu, Qianwei; Wang, Shibo; Bao, Shiqi; Zhang, Xuemei; Ding, Yahui; Wang, Liang; Chen, Yue; Chemical science 15 (2024) 6397–6401; doi:10.1039/d4sc01469c

data_1571304
_publ_section_title
;
 Hypocretenolides: collective total syntheses and activities toward
 metastatic colon cancer.
;
_journal_issue                   17
_journal_name_full               'Chemical science'
_journal_page_first              6397
_journal_page_last               6401
_journal_paper_doi               10.1039/d4sc01469c
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         '0.67(C15 H19 N O2)'
_chemical_formula_sum            'C11 H10 N O'
_chemical_formula_weight         172.20
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-06-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-07-11 deposited with the CCDC.	2024-03-26 downloaded from the CCDC.
;
_cell_angle_alpha                101.163(4)
_cell_angle_beta                 92.706(6)
_cell_angle_gamma                105.082(5)
_cell_formula_units_Z            3
_cell_length_a                   8.5784(7)
_cell_length_b                   8.7025(4)
_cell_length_c                   9.1689(5)
_cell_measurement_reflns_used    2399
_cell_measurement_temperature    301.17(10)
_cell_measurement_theta_max      75.5650
_cell_measurement_theta_min      4.9280
_cell_volume                     644.96(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      301.17(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.952
_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    -43.00   3.00   0.50    0.50    --    0.00 -56.00 166.00   92
  2  \w     14.00  59.00   0.50    0.50    --    0.00  56.00 -50.00   90
  3  \w     49.00  82.00   0.50    0.50    --  101.30 -56.00 166.00   66
  4  \w     77.00 190.00   0.50    0.50    --  101.30  56.00 -50.00  226
  5  \w    -36.00  29.00   0.50    0.50    --    0.00  82.00   0.00  130
  6  \w    -27.00  37.00   0.50    0.50    --    0.00  82.00-150.00  128
  7  \w    -23.00  18.00   0.50    0.50    --    0.00  82.00  90.00   82
  8  \w      1.00  27.00   0.50    0.50    --    0.00  82.00-180.00   52
  9  \w     14.00  56.00   0.50    0.50    --  101.30 -82.00   0.00   84
 10  \w     61.00 133.00   0.50    0.50    --  101.30 -82.00   0.00  144
 11  \w     74.00 120.00   0.50    0.50    --  101.30 -82.00 -90.00   92
 12  \w     14.00 134.00   0.50    0.50    --  101.30 -77.00 150.00  240
 13  \w     66.00 190.00   0.50    0.50    --  101.30  19.00  90.00  248
 14  \w     22.00  48.00   0.50    0.50    --  101.30 -77.00-150.00   52
 15  \w     74.00 125.00   0.50    0.50    --  101.30 -77.00-150.00  102
 16  \w     81.00 115.00   0.50    0.50    --  101.30  38.00  30.00   68
 17  \w    124.00 191.00   0.50    0.50    --  101.30  38.00  30.00  134
 18  \w     76.00 101.00   0.50    0.50    --  101.30 -82.00-180.00   50
 19  \w     86.00 130.00   0.50    0.50    --  101.30 -82.00  60.00   88
 20  \w     84.00 136.00   0.50    0.50    --  101.30 -19.00   0.00  104
 21  \w     42.00  68.00   0.50    0.50    --  101.30 -82.00 -90.00   52
 22  \w     12.00 121.00   0.50    0.50    --  101.30 -57.00   0.00  218
;
_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      0.1221143000
_diffrn_orient_matrix_UB_12      0.1282497000
_diffrn_orient_matrix_UB_13      -0.0628912000
_diffrn_orient_matrix_UB_21      0.0559372000
_diffrn_orient_matrix_UB_22      -0.1364439000
_diffrn_orient_matrix_UB_23      -0.0981315000
_diffrn_orient_matrix_UB_31      -0.1300899000
_diffrn_orient_matrix_UB_32      -0.0124223000
_diffrn_orient_matrix_UB_33      -0.1267278000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5961
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.699
_diffrn_reflns_theta_min         4.943
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_exptl_absorpt_coefficient_mu    0.685
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_F_000             273
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.908
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2556
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.908
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0517
_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^)+(0.1095P)^2^+0.1347P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1588
_refine_ls_wR_factor_ref         0.1668
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2047
_reflns_number_total             2556
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc01469c2.cif
_cod_data_source_block           cbl-13-79
_cod_depositor_comments
'Adding full bibliography for 1571303--1571304.cif.'
_cod_database_code               1571304
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.05
_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:
 C006(H006), C00C(H00E)
2.b Secondary CH2 refined with riding coordinates:
 C005(H00A,H00B), C008(H00C,H00D), C00D(H00F,H00G), C00E(H00H,H00I), C00F(H00J,
 H00K)
2.c Idealised Me refined as rotating group:
 C00H(H00N,H00O,H00P)
;
_shelx_res_checksum              27340
_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 1.744
_oxdiff_exptl_absorpt_empirical_full_min 0.598