Structural elucidation, total synthesis, and cytotoxic activity of effphenol A
Liu, Hongxin; Chen, Shanchong; Zhang, Xiao; Dong, Chunmao; Chen, Yuchan; Liu, Zhaoming; Tan, Haibo; Zhang, Weimin; Organic & Biomolecular Chemistry 18 (2020) 9035–9038; doi:10.1039/D0OB01985B

data_7157781
_publ_section_title
;
 Structural elucidation, total synthesis, and cytotoxic activity of
 effphenol A
;
_journal_issue                   44
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              9035
_journal_page_last               9038
_journal_paper_doi               10.1039/D0OB01985B
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'H2 O, C26 H26 O7'
_chemical_formula_sum            'C26 H28 O8'
_chemical_formula_weight         468.48
_chemical_name_systematic        'Trieffnol C'
_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     direct
_audit_creation_date             2019-08-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-12-30 deposited with the CCDC.	2020-10-21 downloaded from the CCDC.
;
_cell_angle_alpha                88.816(2)
_cell_angle_beta                 73.989(2)
_cell_angle_gamma                76.976(2)
_cell_formula_units_Z            2
_cell_length_a                   8.3229(2)
_cell_length_b                   10.5201(2)
_cell_length_c                   13.8336(3)
_cell_measurement_reflns_used    5339
_cell_measurement_temperature    99.9(9)
_cell_measurement_theta_max      61.9040
_cell_measurement_theta_min      5.3270
_cell_volume                     1133.19(5)
_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, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(9)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.847
_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     34.00  62.00   0.50    0.71    --    0.00  57.00-120.00   56
  2  \w    -54.00 -29.00   0.50    0.71    --    0.00 -57.00-120.00   50
  3  \w      3.00  29.00   0.50    0.71    --    0.00 -82.00  90.00   52
  4  \w    -16.00  16.00   0.50    0.71    --    0.00  57.00-120.00   64
  5  \w    -15.00  12.00   0.50    0.71    --    0.00 -57.00-120.00   54
  6  \w    -17.00  93.00   0.50    2.84    --   70.80 -61.00  60.00  220
  7  \w     21.00 102.00   0.50    2.84    --   70.80 -82.00-180.00  162
  8  \w    -18.00  99.00   0.50    2.84    --   70.80 -82.00 -60.00  234
  9  \w     52.00  78.00   0.50    2.84    --   70.80  61.00 -60.00   52
 10  \w     36.00  79.00   0.50    2.84    --   70.80 -61.00-180.00   86
 11  \w    -19.00   6.00   0.50    2.84    --   70.80 -82.00-180.00   50
 12  \w    -10.00  20.00   0.50    2.84    --   70.80 -61.00-180.00   60
 13  \w     53.00 101.00   0.50    2.84    --   70.80  45.00 -60.00   96
 14  \w    129.00 158.00   0.50    2.84    --   70.80  45.00 -60.00   58
 15  \w     58.00  94.00   0.50    2.84    --   70.80 -82.00 120.00   72
 16  \w     11.00  38.00   0.50    2.84    --   70.80 -82.00 120.00   54
 17  \w    -10.00  15.00   0.50    2.84    --   70.80 -82.00  30.00   50
 18  \w     42.00  95.00   0.50    2.84    --   70.80 -82.00  30.00  106
 19  \w      3.00  93.00   0.50    2.84    --   70.80 -61.00 -60.00  180
 20  \w    101.00 159.00   0.50    2.84    --   70.80  82.00 -30.00  116
 21  \w    -16.00  98.00   0.50    2.84    --   70.80 -82.00  60.00  228
 22  \w    109.00 136.00   0.50    2.84    --   70.80  61.00-150.00   54
;
_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      0.1503241000
_diffrn_orient_matrix_UB_12      0.0656972000
_diffrn_orient_matrix_UB_13      -0.0068889000
_diffrn_orient_matrix_UB_21      0.1284920000
_diffrn_orient_matrix_UB_22      -0.1309834000
_diffrn_orient_matrix_UB_23      -0.0378523000
_diffrn_orient_matrix_UB_31      0.0044498000
_diffrn_orient_matrix_UB_32      0.0341142000
_diffrn_orient_matrix_UB_33      -0.1094038000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.847
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9494
_diffrn_reflns_point_group_measured_fraction_full 0.847
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         62.033
_diffrn_reflns_theta_min         4.318
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.845
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81712
_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            'clear reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_description       cube
_exptl_crystal_F_000             496
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.614
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         3468
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.141
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0404
_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^)+(0.1000P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1338
_refine_ls_wR_factor_ref         0.1391
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3022
_reflns_number_total             3468
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01985b2.cif
_cod_data_source_block           chenshanchong_x7-2_collect
_cod_original_cell_volume        1133.19(4)
_cod_database_code               7157781
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         'C52 H56 O16 '
_reflns_odcompleteness_completeness 99.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     58.86
_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, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O0AA(H0AA,H0AB)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C13(H13), C14(H14), C16(H16), C17(H17), C22(H22)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O4(H4), O5(H5), O6(H6)
;
_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 1.490
_oxdiff_exptl_absorpt_empirical_full_min 0.679