The asymmetric total synthesis of (+)-N-acetyl norloline
Jian-Liang Ye; Yang Liu; Zhi-Ping Yang; Pei-Qiang Huang; Chem.Commun. 52 (2016) 561–; doi:

data_7118429
_publ_section_title
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 The asymmetric total synthesis of (+)-N-acetyl norloline
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_journal_name_full               Chem.Commun.
_journal_page_first              561
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C18 H32 N O6 Si'
_chemical_formula_sum            'C18 H32 N O6 Si'
_chemical_formula_weight         386.54
_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_primary     iterative
_audit_creation_date             2015-01-23
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.19 svn.r3143 for OlexSys, GUI svn.r4992)
;
_audit_update_record
;
2015-09-01 deposited with the CCDC.
2015-10-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8260(15)
_cell_length_b                   9.791(2)
_cell_length_c                   30.820(7)
_cell_measurement_reflns_used    6656
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      25.74
_cell_measurement_theta_min      2.18
_cell_volume                     2059.8(8)
_computing_cell_refinement       'SAINT v6.28A (Bruker, 2002)'
_computing_data_reduction        'SAINT v6.28A (Bruker, 2002)'
_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      273.15
_diffrn_measured_fraction_theta_full 0.9993
_diffrn_measured_fraction_theta_max 0.9339
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            18580
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         28.90
_diffrn_reflns_theta_min         1.32
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.930304
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS v.2.03 (Bruker,200?) was used for absorption correction.
R(int) was 0.0811 before and 0.0342 after correction.
The Ratio of minimum to maximum transmission is 0.9303.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.2464
_exptl_crystal_density_meas      .
_exptl_crystal_description       pillar
_exptl_crystal_F_000             836.7723
_exptl_crystal_size_max          1.0
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.4176
_refine_diff_density_min         -0.3254
_refine_diff_density_rms         0.0592
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.06(13)
_refine_ls_d_res_high            0.7352
_refine_ls_d_res_low             15.4099
_refine_ls_goodness_of_fit_ref   1.0367
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    47
_refine_ls_number_parameters     243
_refine_ls_number_reflns         5071
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0367
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0795P)^2^+0.2115P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1214
_refine_ls_wR_factor_ref         0.1251
_reflns_Friedel_coverage         0.903
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              40
_reflns_limit_l_min              -39
_reflns_number_gt                4495
_reflns_number_total             5071
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c5cc07480k2.cif
_cod_data_source_block           y01222m
_cod_depositor_comments
;
 Updating space group information.

 Antanas Vaitkus,
 2018-08-02

2017-12-13
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '0.15(C18 H32 N O6 Si)'
_cod_original_formula_sum        'C2.667 H4.741 N0.148 O0.889 Si0.148'
_cod_original_formula_units_Z    27
_cod_original_formula_weight     57.27
_cod_database_code               7118429
_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:
 C9(H9), C11(H11), C13(H13), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15a,H15b)
2.c Aromatic/amide H refined with riding coordinates:
 C17(H17)
2.d Idealised Me refined as rotating group:
 C18(H18a,H18b,H18c), C20(H20a,H20b,H20c), C21(H21a,H21b,H21c), C22(H22a,H22b,
 H22c), C23(H23a,H23b,H23c), C24(H24a,H24b,H24c), C25(H25a,H25b,H25c), C26(H26a,
 H26b,H26c)
2.e Idealised tetrahedral OH refined as rotating group:
 O8(H8)
;
_olex2_submission_special_instructions 'No special instructions were received'