Aniline-containing derivatives of parthenolide: Synthesis and anti-chronic lymphocytic leukaemia activity
Quy, Alex S.; Li, Xingjian; Male, Louise; Stankovic, Tatjana; Agathanggelou, Angelo; Fossey, John S.; Tetrahedron 76 (2020) 131631–; doi:10.1016/j.tet.2020.131631

data_1566135
_publ_section_title
;
 Aniline-containing derivatives of parthenolide: Synthesis and
 anti-chronic lymphocytic leukaemia activity
;
_journal_issue                   48
_journal_name_full               Tetrahedron
_journal_page_first              131631
_journal_paper_doi               10.1016/j.tet.2020.131631
_journal_volume                  76
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H24 O4, 0.5(H2 O)'
_chemical_formula_sum            'C16 H25 O4.5'
_chemical_formula_weight         289.36
_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   mixed
_cell_angle_alpha                90
_cell_angle_beta                 105.0673(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.42575(9)
_cell_length_b                   25.7445(3)
_cell_length_c                   9.53536(12)
_cell_measurement_reflns_used    14767
_cell_measurement_temperature    99.9(5)
_cell_measurement_theta_max      74.1350
_cell_measurement_theta_min      3.4240
_cell_volume                     1523.18(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3537
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega -115.00  -20.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6857  -38.0000 -180.0000 95

  2 omega -117.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6857  -77.0000   90.0000 106

  3 omega  -50.00   30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6857   38.0000  120.0000 80

  4 omega  -50.00   30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6857   38.0000    0.0000 80

  5 omega   23.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6857 -125.0000   30.0000 75

  6 omega   23.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6857 -125.0000 -120.0000 75

  7 omega   83.00  178.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      106.6257   30.0000 -120.0000 95

  8 omega   25.00  109.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000   30.0000 84

  9 omega   25.00  109.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000   90.0000 84

 10 omega   79.00  177.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      106.6257   61.0000 -180.0000 98

 11 omega   32.00   91.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -30.0000 -180.0000 59

 12 omega   83.00  178.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      106.6257   30.0000    0.0000 95

 13 omega   94.00  178.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      106.6257  125.0000   90.0000 84

 14 omega   83.00  178.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      106.6257   30.0000   90.0000 95

 15 omega   83.00  178.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      106.6257   30.0000  -90.0000 95

 16 omega   35.00   99.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -45.0000   90.0000 64

 17 omega   32.00   91.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -30.0000   60.0000 59

 18 omega -117.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6857  -77.0000    0.0000 106

 19 omega  -50.00   30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6857   38.0000 -120.0000 80

 20 omega -113.00  -16.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6857  -57.0000  -30.0000 97

 21 omega -117.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6857  -77.0000 -180.0000 106

 22 omega -117.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6857  -77.0000  -60.0000 106

 23 omega   75.00  178.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000  120.0000 103

 24 omega   79.00  177.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      106.6257   61.0000  -90.0000 98

 25 omega   25.00  109.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000 -150.0000 84

 26 omega   79.00  177.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      106.6257   61.0000    0.0000 98

 27 omega   75.00  178.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000   60.0000 103

 28 omega   79.00  177.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      106.6257   61.0000   30.0000 98

 29 omega   75.00  178.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000   90.0000 103

 30 omega   75.00  178.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000  150.0000 103

 31 omega   79.00  177.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      106.6257   61.0000 -150.0000 98

 32 omega   79.00  177.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      106.6257   61.0000  -60.0000 98

 33 omega   16.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6857   57.0000  -60.0000 67
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0210397000
_diffrn_orient_matrix_UB_12      0.0225695000
_diffrn_orient_matrix_UB_13      -0.1526933000
_diffrn_orient_matrix_UB_21      0.1464633000
_diffrn_orient_matrix_UB_22      0.0457852000
_diffrn_orient_matrix_UB_23      0.0674891000
_diffrn_orient_matrix_UB_31      0.1993427000
_diffrn_orient_matrix_UB_32      -0.0312268000
_diffrn_orient_matrix_UB_33      -0.0115091000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            28047
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.138
_diffrn_reflns_theta_min         3.433
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.741
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.967
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_description       plate
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.255
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.0433
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 2602 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     392
_refine_ls_number_reflns         5683
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0264
_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^)+(0.0300P)^2^+0.3220P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0622
_refine_ls_wR_factor_ref         0.0637
_reflns_Friedel_coverage         0.952
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                5469
_reflns_number_total             5683
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            7.cif
_cod_data_source_block           7
_cod_depositor_comments
;

2022-05-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C32 H50 O9'
_cod_original_formula_weight         578.72
_cod_original_formula_moiety         '2(C16 H24 O4), H2 O'
_cod_original_formula_units_Z            2
_cod_original_cell_volume        1523.19(3)
_cod_database_code               1566135
_chemical_oxdiff_formula         'C16 H24 O4'
_reflns_odcompleteness_completeness 99.96
_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:
 C4(H4), C5(H5), C6(H6), C11(H11), C104(H104), C105(H105), C106(H106),
 C111(H111)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C15(H15A,H15B), C16(H16A,H16B), C109(H10H,H10I),
 C110(H11A,H11B), C115(H11I,H11J), C116(H11K,H11L)
2.c X=CH2 refined with riding coordinates:
 C3(H3A,H3B), C103(H10C,H10D)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C108(H10E,H10F,
 H10G), C113(H11C,H11D,H11E), C114(H11F,H11G,H11H)
;
_shelx_res_checksum              29380
_shelx_hkl_checksum              83096
_olex2_submission_special_instructions 'No special instructions were received'