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_7159611
_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'
_chemical_formula_sum            'C30 H48 O5'
_chemical_formula_weight         488.68
_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   geom
_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            12
_cell_length_a                   12.7887(10)
_cell_length_b                   13.3649(10)
_cell_length_c                   53.155(4)
_cell_measurement_reflns_used    9994
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      56.860
_cell_measurement_theta_min      3.220
_cell_volume                     9085.2(12)
_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 0.994
_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  0.1019
_diffrn_reflns_av_unetI/netI     0.0583
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       66
_diffrn_reflns_limit_l_min       -66
_diffrn_reflns_number            96778
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         57.041
_diffrn_reflns_theta_min         2.966
_diffrn_source_current           2.86
_diffrn_source_power             0.1997996
_diffrn_source_voltage           69.86
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.358
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.5827
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1485 before and 0.0844 after correction.
The Ratio of minimum to maximum transmission is 0.7757.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.072
_exptl_crystal_description       needle
_exptl_crystal_F_000             3216
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.537
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 5611 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.26(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     973
_refine_ls_number_reflns         18153
_refine_ls_number_restraints     616
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0657
_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^)+(0.1071P)^2^+3.6336P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1791
_refine_ls_wR_factor_ref         0.1865
_reflns_Friedel_coverage         0.784
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.953
_reflns_number_gt                15349
_reflns_number_total             18153
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01625k2.cif
_cod_data_source_block           1_sq
_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               7159611
_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
2. Restrained distances
 O02Z-C02U
 1.22 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
O02P \\sim C02U \\sim O02Z \\sim C02T \\sim C02G \\sim C02X \\sim C02M \\sim
C02V \\sim C030 \\sim C02Y \\sim C02W \\sim C02S \\sim C02A \\sim C01O \\sim
O00F \\sim C00V \\sim C01B \\sim C01I \\sim C02L \\sim O009 \\sim C00Y \\sim
C01K \\sim C013 \\sim C026 \\sim C01V \\sim C00U \\sim C01N \\sim C01M \\sim
C012 \\sim C018 \\sim C02K \\sim C01X \\sim C02I \\sim C02B \\sim O00B: within
2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
Uanis(C02X) \\sim Ueq, Uanis(C02T) \\sim Ueq, Uanis(O02P) \\sim Ueq,
Uanis(C02U) \\sim Ueq, Uanis(O02Z) \\sim Ueq, Uanis(C02S) \\sim Ueq,
Uanis(C02Y) \\sim Ueq, Uanis(C02V) \\sim Ueq, Uanis(C02W) \\sim Ueq,
Uanis(C030) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
4. Rigid body (RIGU) restrains
 O02P, C02U, O02Z, C02T, C02G, C02X, C02M, C02V, C030, C02Y, C02W, C02S, C02A,
 C01O, O00F, C00V, C01B, C01I, C02L, O009, C00Y, C01K, C013, C026, C01V, C00U,
 C01N, C01M, C012, C018, C02K, C01X, C02I, C02B, O00B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
5.a Ternary CH refined with riding coordinates:
 C00E(HD), C00I(HE), C00J(HF), C00O(HK), C00W(HL), C010(HP), C012(H012),
 C013(H013), C019(HZ), C01G(H6), C01H(H7), C01O(H01O), C01X(H01X), C02D(H50),
 C02G(H02H)
5.b Secondary CH2 refined with riding coordinates:
 C00K(HG,HH), C00L(HI,HJ), C011(HQ,HR), C014(HS,HT), C016(HX,HY), C01F(H4,H5),
 C01J(H8,H9), C01K(H01D,H01E), C01L(H10,H11), C01M(H01F,H01G), C01Q(H12,H13),
 C01R(H14,H15), C01S(H16,H17), C01V(H01K,H01L), C01W(H21,H22), C01Y(H23,H24),
 C01Z(H25,H26), C023(H33,H34), C025(H38,H39), C026(H02A,H02B), C028(H43,H44),
 C02A(H02C,H02D), C02C(H48,H49), C02E(H51,H52), C02I(H02I,H02J), C02J(H59,H60),
 C02M(H02Q,H02R), C02S(H02T,H02U), C02X(H02Y,H70), C02Y(H02Z,H71)
5.c Idealised Me refined as rotating group:
 C00X(HM,HN,HO), C015(HU,HV,HW), C01B(H01A,H01B,H01C), C01C(H1,H2,H3),
 C01N(H01H,H01I,H01J), C01U(H18,H19,H20), C021(H27,H28,H29), C022(H30,H31,H32),
 C024(H35,H36,H37), C027(H40,H41,H42), C029(H45,H46,H47), C02B(H02E,H02F,H02G),
 C02F(H53,H54,H55), C02H(H56,H57,H58), C02K(H02K,H02L,H02M), C02L(H02N,H02O,
 H02P), C02N(H61,H62,H63), C02O(H64,H65,H66), C02Q(H67,H68,H69), C02W(H02V,H02W,
 H02X), C030(H03A,H03B,H03C)
5.d Idealised tetrahedral OH refined as rotating group:
 O005(H), O008(HA), O00A(HB), O00B(H00B), O00C(HC), O02P(H02S)
;
_shelx_res_checksum              61642
_shelx_fab_checksum              57738
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'