Total Synthesis and Structural Reassignment of Aranorosinol A, Aranorosinol B, and EI-2128-1.
Yu, Haiyong; Tian, Yingyuan; Zong, Yan; Zhang, Jianyu; Xu, Tao; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00028

data_4038044
_publ_section_title
;
 Total Synthesis and Structural Reassignment of Aranorosinol A,
 Aranorosinol B, and EI-2128-1.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00028
_journal_year                    2020
_chemical_formula_moiety
'2(C25 H32 Br N O7 Si), 2(C25 H35 Br N O7 Si), C H2 Cl2'
_chemical_formula_sum            'C100 H142 Br4 Cl2 N4 O28 Si4'
_chemical_formula_weight         2351.07
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-01-09
_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            4
_cell_length_a                   24.660(2)
_cell_length_b                   32.376(3)
_cell_length_c                   14.0760(13)
_cell_measurement_reflns_used    4752
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.593
_cell_measurement_theta_min      0.286
_cell_volume                     11238.2(17)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      298.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1414
_diffrn_reflns_av_unetI/netI     0.1554
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            53015
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.284
_exptl_absorpt_coefficient_mu    1.595
_exptl_absorpt_correction_T_max  0.839
_exptl_absorpt_correction_T_min  0.525
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_description       block
_exptl_crystal_F_000             4896
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.552
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.764
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     655
_refine_ls_number_reflns         9893
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.768
_refine_ls_R_factor_all          0.1942
_refine_ls_R_factor_gt           0.0565
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0773P)^2^+0.0001P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1287
_refine_ls_wR_factor_ref         0.1563
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3275
_reflns_number_total             9893
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00028_si_004.cif
_cod_data_source_block           171219d
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/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 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        11238.1(17)
_cod_database_code               4038044
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.844
_shelx_estimated_absorpt_t_min   0.561
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C13-C14
 1.45 with sigma of 0.02
 C38-C39
 1.45 with sigma of 0.002
3. Others
 Fixed Sof: H51A(0.5) H51B(0.5)
4.a Ternary CH refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9A), C11(H11), C12(H12), C30(H30), C31(H31),
 C33(H33), C34(H34), C36(H36), C37(H37)
4.b Secondary CH2 refined with riding coordinates:
 N1(H1D,H1E), C3(H3A,H3B), C10(H10A,H10B), N4(H2A,H2B), C13(H13A,H13B),
 C15(H15A,H15B), C17(H17A,H17B), C28(H28A,H28B), C35(H35A,H35B), C38(H38A,H38B),
  C40(H40A,H40B), C42(H42A,H42B), C51(H51A,H51B)
4.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C22(H22), C24(H24), C25(H25), C46(H46), C47(H47), C49(H49), C50(H50)
4.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C26(H26A,H26B,
 H26C), C39(H39A,H39B,H39C), C41(H41A,H41B,H41C), C43(H43A,H43B,H43C)
4.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O9(H9)
;
_shelx_res_checksum              5400
_shelx_hkl_checksum              19861
_olex2_submission_special_instructions 'No special instructions were received'