Stereocontrol in an intermolecular Schmidt reaction of equilibrating hydroxyalkyl allylic azides.
Liu, Ruzhang; Wang, Juan; Wu, Hao; Quan, Xianfeng; Wang, Shilin; Guo, Jiandong; Wang, Yang; Li, Heting; Chemical communications (Cambridge, England) 60 (2024) 4362–4365; doi:10.1039/d4cc00907j

data_7132891
_publ_section_title
;
 Stereocontrol in an intermolecular Schmidt reaction of equilibrating
 hydroxyalkyl allylic azides.
;
_journal_issue                   32
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4362
_journal_page_last               4365
_journal_paper_doi               10.1039/d4cc00907j
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         '2(C16 H21 N O2)'
_chemical_formula_sum            'C32 H42 N2 O4'
_chemical_formula_weight         518.67
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2021-05-09
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_audit_update_record
;
2022-06-05 deposited with the CCDC.	2024-03-26 downloaded from the CCDC.
;
_cell_angle_alpha                88.886(3)
_cell_angle_beta                 84.246(3)
_cell_angle_gamma                83.434(3)
_cell_formula_units_Z            2
_cell_length_a                   5.6228(6)
_cell_length_b                   11.5801(11)
_cell_length_c                   22.772(2)
_cell_measurement_reflns_used    5695
_cell_measurement_temperature    296
_cell_measurement_theta_max      22.477
_cell_measurement_theta_min      2.513
_cell_volume                     1465.5(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_av_unetI/netI     0.0868
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            22640
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.424
_diffrn_reflns_theta_min         0.899
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6665
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1412 before and 0.0612 after correction.
The Ratio of minimum to maximum transmission is 0.8940.
The \l/2 correction factor is Not present.
;
_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    1.175
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.518
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       0.083(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         6660
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.1905
_refine_ls_R_factor_gt           0.0987
_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^)+(0.1522P)^2^+1.4637P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2986
_refine_ls_wR_factor_ref         0.3473
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3212
_reflns_number_total             6660
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00907j2.cif
_cod_data_source_block           15b
_cod_depositor_comments
'Adding full bibliography for 7132889--7132892.cif.'
_cod_original_cell_volume        1465.6(3)
_cod_database_code               7132891
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.985
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Others
 Sof(H31A)=Sof(C32)=Sof(H32C)=Sof(H32D)=1-FVAR(1)
 Sof(H31)=Sof(C32A)=Sof(H32A)=Sof(H32B)=FVAR(1)
 Sof(H13C)=Sof(H13D)=Sof(O2)=Sof(H2)=1-FVAR(2)
 Sof(O2A)=Sof(H2AA)=Sof(H13A)=Sof(H13B)=FVAR(2)
3.a Ternary CH refined with riding coordinates:
 C30(H30), C19(H19), C3(H3), C14(H14)
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C29(H29A,H29B), C17(H17A,H17B), C1(H1A,H1B), C18(H18A,H18B),
 C2(H2A,H2B), C21(H21A,H21B), C5(H5A,H5B), C20(H20A,H20B), C13(H13A,H13B),
 C13(H13C,H13D)
3.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C31(H31), C31(H31A), C12(H12), C10(H10), C11(H11), C24(H24), C9(H9),
 C15(H15), C28(H28), C27(H27), C26(H26), C25(H25)
3.d Tetrahedral OH refined with riding coordinates:
 O2(H2)
3.e X=CH2 refined with riding coordinates:
 C16(H16A,H16B), C32A(H32A,H32B), C32(H32C,H32D)
3.f Idealised tetrahedral OH refined as rotating group:
 O4(H4), O2A(H2AA)
;
_shelx_res_checksum              88096
_olex2_submission_special_instructions 'No special instructions were received'