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_1571303
_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         'C15 H16 O3'
_chemical_formula_sum            'C15 H16 O3'
_chemical_formula_weight         244.27
_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     dual
_audit_creation_date             2022-09-15
_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                90
_cell_angle_beta                 92.6560(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.3154(2)
_cell_length_b                   9.74840(10)
_cell_length_c                   11.29700(10)
_cell_measurement_reflns_used    13664
_cell_measurement_temperature    99.99(11)
_cell_measurement_theta_max      76.1620
_cell_measurement_theta_min      4.9290
_cell_volume                     2454.90(4)
_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      N~2~
_diffrn_ambient_temperature      99.99(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.973
_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  33.00   0.50    0.50    --    0.00 -82.00 -30.00  144
  2  \w    -38.00  36.00   0.50    0.50    --    0.00 -82.00  60.00  148
  3  \w    -39.00  36.00   0.50    0.50    --    0.00 -82.00-120.00  150
  4  \w     12.00 127.00   0.50    0.50    --  101.90 -77.00 -30.00  230
  5  \w     43.00 133.00   0.50    0.50    --  101.90 -82.00  90.00  180
  6  \w     12.00 120.00   0.50    0.50    --  101.90 -57.00-150.00  216
  7  \w     47.00 123.00   0.50    0.50    --  101.90 -82.00-150.00  152
  8  \w     16.00 123.00   0.50    0.50    --  101.90 -57.00  60.00  214
  9  \w     76.00 191.00   0.50    0.50    --  101.90  38.00 -30.00  230
 10  \w     24.00 129.00   0.50    0.50    --  101.90 -57.00 -30.00  210
 11  \w     83.00 191.00   0.50    0.50    --  101.90   0.00-120.00  216
 12  \w     27.00  53.00   0.50    0.50    --  101.90   0.00-120.00   52
;
_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      0.0590280000
_diffrn_orient_matrix_UB_12      0.0655442000
_diffrn_orient_matrix_UB_13      -0.0374401000
_diffrn_orient_matrix_UB_21      0.0204495000
_diffrn_orient_matrix_UB_22      -0.1396903000
_diffrn_orient_matrix_UB_23      -0.0474038000
_diffrn_orient_matrix_UB_31      -0.0295591000
_diffrn_orient_matrix_UB_32      0.0343321000
_diffrn_orient_matrix_UB_33      -0.1223829000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19866
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.394
_diffrn_reflns_theta_min         4.952
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_exptl_absorpt_coefficient_mu    0.740
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94211
_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_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         5021
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0355
_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^)+(0.0412P)^2^+0.9495P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0918
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4620
_reflns_number_total             5021
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc01469c2.cif
_cod_data_source_block           cbl-14-6
_cod_depositor_comments
;
Adding full bibliography for 1571303--1571304.cif.

2025-06-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C30 H32 O6'
_cod_original_formula_weight         488.55
_cod_original_formula_moiety         '2(C15 H16 O3)'
_cod_original_formula_units_Z            4
_cod_database_code               1571303
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.51
_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:
 C00G(H00O), C00P(H00P)
2.b Secondary CH2 refined with riding coordinates:
 C00B(H00L,H00M), C00N(H00A,H00B), C00R(H00V,H00X), C00S(H00Y,H), C00X(H00H,
 H00I), C00Y(H00J,H00K)
2.c Aromatic/amide H refined with riding coordinates:
 C00E(H00N), C00W(H00W)
2.d X=CH2 refined with riding coordinates:
 C00K(H00Q,H00R), C00Q(H00C,H00D)
2.e Idealised Me refined as rotating group:
 C00M(H00S,H00T,H00U), C00V(H00E,H00F,H00G), C00Z(H00Z,HA,HB), C010(H01A,H01B,
 H01C)
;
_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 1.237
_oxdiff_exptl_absorpt_empirical_full_min 0.754