Gram-scale synthesis of alstoscholarinoid B <i>via</i> a bio-inspired strategy.
He, Long; Zhang, Wenting; Zhang, Xiaocheng; Wu, Xiaohui; Han, Yimeng; Yan, Jiahang; Xie, Weiqing; Organic & biomolecular chemistry 21 (2023) 9346–9355; doi:10.1039/d3ob01625k

data_7159610
_publ_section_title
;
 Gram-scale synthesis of alstoscholarinoid B <i>via</i> a bio-inspired
 strategy.
;
_journal_issue                   47
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9346
_journal_page_last               9355
_journal_paper_doi               10.1039/d3ob01625k
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H48 O5, H2 O'
_chemical_formula_sum            'C30 H50 O6'
_chemical_formula_weight         506.70
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-06-15
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_audit_update_record
;
2023-08-20 deposited with the CCDC.	2023-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2344(5)
_cell_length_b                   16.0149(9)
_cell_length_c                   17.8661(9)
_cell_measurement_reflns_used    9821
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      57.024
_cell_measurement_theta_min      3.224
_cell_volume                     2642.2(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0792
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            29126
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         57.033
_diffrn_reflns_theta_min         3.224
_diffrn_source_current           2.86
_diffrn_source_power             0.19977099999999998
_diffrn_source_voltage           69.85
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.440
_exptl_absorpt_correction_T_max  0.7253
_exptl_absorpt_correction_T_min  0.6458
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1612 before and 0.0956 after correction.
The Ratio of minimum to maximum transmission is 0.8904.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_description       block
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1684 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.21(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         5339
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0456
_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^)+(0.0541P)^2^+0.6201P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1162
_reflns_Friedel_coverage         0.755
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                4544
_reflns_number_total             5339
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01625k2.cif
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_absolute_configuration' value 'AD' was changed
to 'ad' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7159609--7159611.cif.
;
_cod_database_code               7159610
_shelx_shelxl_version_number     2018/3
_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. Restrained distances
 H5C-H6_$1
 2.1 with sigma of 0.001
 H6_$1-H5D
 2.1 with sigma of 0.001
3.a Everything fixed:
 O5, H5C, H5D
3.b Ternary CH refined with riding coordinates:
 C16(H16), C17(H17), C22(H22), C7(H7), C27(H27)
3.c Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C25(H25A,H25B), C10(H10A,H10B), C20(H20A,H20B), C21(H21A,
 H21B), C5(H5A,H5B), C6(H6A,H6B), C4(H4A,H4B), C26(H26A,H26B)
3.d Aromatic/amide H refined with riding coordinates:
 C15(H15)
3.e Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C23(H23A,H23B,H23C), C30(H30A,H30B,H30C), C13(H13A,H13B,
 H13C), C29(H29A,H29B,H29C), C2(H2A,H2B,H2C), C1(H1A,H1B,H1C)
3.f Idealised tetrahedral OH refined as rotating group:
 O4(H4), O6(H6), O1(H1)
;
_shelx_res_checksum              70484
_olex2_submission_special_instructions 'No special instructions were received'