#------------------------------------------------------------------------------
#$Date: 2024-05-05 04:33:51 +0300 (Sun, 05 May 2024) $
#$Revision: 291560 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/13/1571304.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1571304
loop_
_publ_author_name
'Chen, Bolin'
'Zhang, Xijing'
'Yang, Yufen'
'Xu, Dongdong'
'Wu, Qianwei'
'Wang, Shibo'
'Bao, Shiqi'
'Zhang, Xuemei'
'Ding, Yahui'
'Wang, Liang'
'Chen, Yue'
_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -43.00   3.00   0.50    0.50    --    0.00 -56.00 166.00   92
  2  ω     14.00  59.00   0.50    0.50    --    0.00  56.00 -50.00   90
  3  ω     49.00  82.00   0.50    0.50    --  101.30 -56.00 166.00   66
  4  ω     77.00 190.00   0.50    0.50    --  101.30  56.00 -50.00  226
  5  ω    -36.00  29.00   0.50    0.50    --    0.00  82.00   0.00  130
  6  ω    -27.00  37.00   0.50    0.50    --    0.00  82.00-150.00  128
  7  ω    -23.00  18.00   0.50    0.50    --    0.00  82.00  90.00   82
  8  ω      1.00  27.00   0.50    0.50    --    0.00  82.00-180.00   52
  9  ω     14.00  56.00   0.50    0.50    --  101.30 -82.00   0.00   84
 10  ω     61.00 133.00   0.50    0.50    --  101.30 -82.00   0.00  144
 11  ω     74.00 120.00   0.50    0.50    --  101.30 -82.00 -90.00   92
 12  ω     14.00 134.00   0.50    0.50    --  101.30 -77.00 150.00  240
 13  ω     66.00 190.00   0.50    0.50    --  101.30  19.00  90.00  248
 14  ω     22.00  48.00   0.50    0.50    --  101.30 -77.00-150.00   52
 15  ω     74.00 125.00   0.50    0.50    --  101.30 -77.00-150.00  102
 16  ω     81.00 115.00   0.50    0.50    --  101.30  38.00  30.00   68
 17  ω    124.00 191.00   0.50    0.50    --  101.30  38.00  30.00  134
 18  ω     76.00 101.00   0.50    0.50    --  101.30 -82.00-180.00   50
 19  ω     86.00 130.00   0.50    0.50    --  101.30 -82.00  60.00   88
 20  ω     84.00 136.00   0.50    0.50    --  101.30 -19.00   0.00  104
 21  ω     42.00  68.00   0.50    0.50    --  101.30 -82.00 -90.00   52
 22  ω     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       'ω 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/[σ²(Fo²)+(0.1095P)²+0.1347P] where P=(Fo²+2Fc²)/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 > 2σ(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
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)
;
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.73491(14) 0.52739(12) 0.58807(13) 0.0494(3) Uani 1 1 d . . . . .
O002 O 0.60652(18) 1.00566(14) 0.79391(17) 0.0658(4) Uani 1 1 d . . . . .
N003 N 0.6721(2) 1.04539(18) 0.6625(2) 0.0642(5) Uani 1 1 d . . . . .
C004 C 0.76903(19) 0.70052(18) 0.61429(19) 0.0441(4) Uani 1 1 d . . . . .
C005 C 0.6717(2) 0.46432(19) 0.7125(2) 0.0521(4) Uani 1 1 d . . . . .
H00A H 0.6563 0.3474 0.6907 0.062 Uiso 1 1 calc R . . . .
H00B H 0.5662 0.4835 0.7245 0.062 Uiso 1 1 calc R . . . .
C006 C 0.6137(2) 0.76118(18) 0.63026(19) 0.0442(4) Uani 1 1 d . . . . .
H006 H 0.5252 0.6844 0.5601 0.053 Uiso 1 1 calc R . . . .
C007 C 0.8284(2) 0.7523(2) 0.4708(2) 0.0529(4) Uani 1 1 d . . . . .
C008 C 0.9018(2) 0.7760(2) 0.7435(2) 0.0502(4) Uani 1 1 d . . . . .
H00C H 0.9240 0.8936 0.7618 0.060 Uiso 1 1 calc R . . . .
H00D H 1.0003 0.7484 0.7150 0.060 Uiso 1 1 calc R . . . .
C009 C 0.7780(2) 0.5375(2) 0.8566(2) 0.0521(4) Uani 1 1 d . . . . .
C00A C 0.5422(2) 0.82666(19) 0.7725(2) 0.0513(4) Uani 1 1 d . . . . .
C00B C 0.6684(2) 0.9132(2) 0.5725(2) 0.0535(4) Uani 1 1 d . . . . .
C00C C 0.8583(2) 0.7198(2) 0.8881(2) 0.0533(4) Uani 1 1 d . . . . .
H00E H 0.9607 0.7392 0.9498 0.064 Uiso 1 1 calc R . . . .
C00D C 0.5808(2) 0.7844(2) 0.9205(2) 0.0581(5) Uani 1 1 d . . . . .
H00F H 0.5303 0.6691 0.9117 0.070 Uiso 1 1 calc R . . . .
H00G H 0.5289 0.8427 0.9957 0.070 Uiso 1 1 calc R . . . .
C00E C 0.7594(3) 0.8886(2) 0.4402(2) 0.0642(5) Uani 1 1 d . . . . .
H00H H 0.8446 0.9859 0.4371 0.077 Uiso 1 1 calc R . . . .
H00I H 0.6881 0.8551 0.3477 0.077 Uiso 1 1 calc R . . . .
C00F C 0.7577(3) 0.8192(3) 0.9790(2) 0.0642(5) Uani 1 1 d . . . . .
H00J H 0.7618 0.8007 1.0799 0.077 Uiso 1 1 calc R . . . .
H00K H 0.8096 0.9338 0.9852 0.077 Uiso 1 1 calc R . . . .
C00G C 0.7951(3) 0.4443(3) 0.9506(3) 0.0674(6) Uani 1 1 d . . . . .
C00H C 0.3589(2) 0.7880(3) 0.7366(3) 0.0683(6) Uani 1 1 d . . . . .
H00N H 0.3145 0.8457 0.8168 0.102 Uiso 1 1 calc GR . . . .
H00O H 0.3110 0.6730 0.7245 0.102 Uiso 1 1 calc GR . . . .
H00P H 0.3358 0.8210 0.6458 0.102 Uiso 1 1 calc GR . . . .
C00I C 0.9281(3) 0.6891(3) 0.3889(3) 0.0726(6) Uani 1 1 d . . . . .
H00L H 0.738(3) 0.321(3) 0.925(3) 0.078(7) Uiso 1 1 d . . . . .
H00M H 0.857(3) 0.488(3) 1.043(3) 0.077(7) Uiso 1 1 d . . . . .
H00Q H 0.976(3) 0.732(3) 0.302(3) 0.085(7) Uiso 1 1 d . . . . .
H00R H 0.968(3) 0.600(3) 0.419(3) 0.087(8) Uiso 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C004 O001 C005 112.30(12) . . ?
N003 O002 C00A 109.80(13) . . ?
C00B N003 O002 107.97(14) . . ?
O001 C004 C006 112.98(12) . . ?
O001 C004 C007 107.29(13) . . ?
O001 C004 C008 108.97(13) . . ?
C007 C004 C006 102.33(13) . . ?
C008 C004 C006 114.93(14) . . ?
C008 C004 C007 109.90(13) . . ?
O001 C005 H00A 108.8 . . ?
O001 C005 H00B 108.8 . . ?
O001 C005 C009 113.96(14) . . ?
H00A C005 H00B 107.7 . . ?
C009 C005 H00A 108.8 . . ?
C009 C005 H00B 108.8 . . ?
C004 C006 H006 108.6 . . ?
C00A C006 C004 129.52(14) . . ?
C00A C006 H006 108.6 . . ?
C00B C006 C004 99.16(13) . . ?
C00B C006 H006 108.6 . . ?
C00B C006 C00A 100.11(13) . . ?
C00E C007 C004 110.25(15) . . ?
C00I C007 C004 124.32(18) . . ?
C00I C007 C00E 125.42(19) . . ?
C004 C008 H00C 108.9 . . ?
C004 C008 H00D 108.9 . . ?
C004 C008 C00C 113.45(14) . . ?
H00C C008 H00D 107.7 . . ?
C00C C008 H00C 108.9 . . ?
C00C C008 H00D 108.9 . . ?
C005 C009 C00C 117.00(14) . . ?
C00G C009 C005 119.72(19) . . ?
C00G C009 C00C 123.26(19) . . ?
O002 C00A C006 103.38(13) . . ?
O002 C00A C00D 106.52(15) . . ?
O002 C00A C00H 106.34(14) . . ?
C00D C00A C006 121.23(14) . . ?
C00D C00A C00H 110.12(16) . . ?
C00H C00A C006 108.13(16) . . ?
N003 C00B C006 116.25(17) . . ?
N003 C00B C00E 128.66(18) . . ?
C00E C00B C006 111.69(15) . . ?
C008 C00C H00E 106.8 . . ?
C008 C00C C00F 112.60(15) . . ?
C009 C00C C008 110.79(14) . . ?
C009 C00C H00E 106.8 . . ?
C009 C00C C00F 112.67(16) . . ?
C00F C00C H00E 106.8 . . ?
C00A C00D H00F 107.7 . . ?
C00A C00D H00G 107.7 . . ?
C00A C00D C00F 118.31(17) . . ?
H00F C00D H00G 107.1 . . ?
C00F C00D H00F 107.7 . . ?
C00F C00D H00G 107.7 . . ?
C007 C00E H00H 111.7 . . ?
C007 C00E H00I 111.7 . . ?
C00B C00E C007 100.38(14) . . ?
C00B C00E H00H 111.7 . . ?
C00B C00E H00I 111.7 . . ?
H00H C00E H00I 109.5 . . ?
C00C C00F H00J 108.1 . . ?
C00C C00F H00K 108.1 . . ?
C00D C00F C00C 116.76(15) . . ?
C00D C00F H00J 108.1 . . ?
C00D C00F H00K 108.1 . . ?
H00J C00F H00K 107.3 . . ?
C009 C00G H00L 120.7(13) . . ?
C009 C00G H00M 121.4(16) . . ?
H00L C00G H00M 118(2) . . ?
C00A C00H H00N 109.5 . . ?
C00A C00H H00O 109.5 . . ?
C00A C00H H00P 109.5 . . ?
H00N C00H H00O 109.5 . . ?
H00N C00H H00P 109.5 . . ?
H00O C00H H00P 109.5 . . ?
C007 C00I H00Q 123.7(15) . . ?
C007 C00I H00R 119.4(15) . . ?
H00Q C00I H00R 117(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C004 1.4273(17) . ?
O001 C005 1.429(2) . ?
O002 N003 1.419(2) . ?
O002 C00A 1.4811(19) . ?
N003 C00B 1.271(2) . ?
C004 C006 1.559(2) . ?
C004 C007 1.539(2) . ?
C004 C008 1.521(2) . ?
C005 H00A 0.9700 . ?
C005 H00B 0.9700 . ?
C005 C009 1.497(3) . ?
C006 H006 0.9800 . ?
C006 C00A 1.540(2) . ?
C006 C00B 1.491(2) . ?
C007 C00E 1.521(3) . ?
C007 C00I 1.320(3) . ?
C008 H00C 0.9700 . ?
C008 H00D 0.9700 . ?
C008 C00C 1.530(3) . ?
C009 C00C 1.520(2) . ?
C009 C00G 1.320(3) . ?
C00A C00D 1.517(3) . ?
C00A C00H 1.525(3) . ?
C00B C00E 1.484(3) . ?
C00C H00E 0.9800 . ?
C00C C00F 1.538(3) . ?
C00D H00F 0.9700 . ?
C00D H00G 0.9700 . ?
C00D C00F 1.517(3) . ?
C00E H00H 0.9700 . ?
C00E H00I 0.9700 . ?
C00F H00J 0.9700 . ?
C00F H00K 0.9700 . ?
C00G H00L 1.03(3) . ?
C00G H00M 0.93(3) . ?
C00H H00N 0.9600 . ?
C00H H00O 0.9600 . ?
C00H H00P 0.9600 . ?
C00I H00Q 1.01(3) . ?
C00I H00R 1.00(3) . ?
