Euroticins A and B, Two Pairs of Highly Constructed Salicylaldehyde Derivative Enantiomers from a Marine-Derived Fungus Eurotium sp. SCSIO F452
Zhong, Weimao; Chen, Yuchan; Mai, Zhimao; Wei, Xiaoyi; Wang, Junfeng; Zeng, Qi; Chen, Xiayu; Tian, Xinpeng; Zhang, Weimin; Wang, Fazuo; Zhang, Si; The Journal of Organic Chemistry  (2020) –; doi:10.1021/acs.joc.0c01407

data_4038738
_publ_section_title
;
 Euroticins A and B, Two Pairs of Highly Constructed Salicylaldehyde
 Derivative Enantiomers from a Marine-Derived Fungus Eurotium sp. SCSIO
 F452
;
_journal_name_full               'The Journal of Organic Chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01407
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H22 O4'
_chemical_formula_sum            'C19 H22 O4'
_chemical_formula_weight         314.36
_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_Hall           'P 4nw 2abw'
_space_group_name_H-M_alt        'P 43 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-03-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.70420(10)
_cell_length_b                   10.70420(10)
_cell_length_c                   30.0297(4)
_cell_measurement_reflns_used    5743
_cell_measurement_temperature    99.8(8)
_cell_measurement_theta_max      73.6380
_cell_measurement_theta_min      5.0570
_cell_volume                     3440.80(6)
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.8(8)
_diffrn_detector                 'Pilatus3R 200K-A'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.977
_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    -17.00  10.75   0.25    2.05    --    0.00  19.00 -60.00  111
  2  \w     29.00  83.00   0.25    2.05    --    0.00  19.00 -60.00  216
  3  \w     90.00 139.75   0.25    9.00    --   95.20  82.00 -30.00  199
  4  \w     27.00  84.75   0.25    9.00    --   95.20 -45.00-120.00  231
  5  \w     88.00 182.25   0.25    9.00    --   95.20  82.00-150.00  377
  6  \w      6.00  84.50   0.25    9.00    --   95.20 -82.00 -90.00  314
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1278249000
_diffrn_orient_matrix_UB_12      -0.0379761000
_diffrn_orient_matrix_UB_13      -0.0192752000
_diffrn_orient_matrix_UB_21      -0.0605806000
_diffrn_orient_matrix_UB_22      0.1144683000
_diffrn_orient_matrix_UB_23      0.0223183000
_diffrn_orient_matrix_UB_31      0.0266002000
_diffrn_orient_matrix_UB_32      0.0785552000
_diffrn_orient_matrix_UB_33      -0.0419693000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            9204
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.125
_diffrn_reflns_theta_min         4.385
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'MicroMax 007 (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.683
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41817
_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 light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1072 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.12(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3371
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0407
_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^)+(0.0682P)^2^+0.3196P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1125
_reflns_Friedel_coverage         0.639
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.940
_reflns_number_gt                3064
_reflns_number_total             3371
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01407_si_003.cif
_cod_data_source_block           zhongweimao_wf452-66a-2_collect
_cod_original_cell_volume        3440.80(8)
_cod_database_code               4038738
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C152 H176 O32 '
_shelx_estimated_absorpt_t_max   0.935
_shelx_estimated_absorpt_t_min   0.935
_reflns_odcompleteness_completeness 99.84
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2"(H2"), C7(H7), C6"(H6"), C1"(H1"), C5"(H5")
2.b Secondary CH2 refined with riding coordinates:
 C3"(H3"A,H3"B), C4"(H4"A,H4"B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C1'(H1'), C2'(H2')
2.d Idealised Me refined as rotating group:
 C7"(H7"A,H7"B,H7"C), C5'(H5'A,H5'B,H5'C), C4'(H4'A,H4'B,H4'C)
2.e Idealised tetrahedral OH refined as rotating group:
 O22(H22)
;
_shelx_res_checksum              43849
_shelx_hkl_checksum              38655
_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 2.233
_oxdiff_exptl_absorpt_empirical_full_min 0.455