Efficient synthesis of tetrazole hemiaminal silyl ethers via three-component hemiaminal silylation.
Xie, Ming-Sheng; Cheng, Xuan; Chen, Yang-Guang; Wu, Xiao-Xia; Qu, Gui-Rong; Guo, Hai-Ming; Organic & biomolecular chemistry 16 (2018) 6890–6894; doi:10.1039/c8ob02089b

data_7156425
_publ_section_title
;
 Efficient synthesis of tetrazole hemiaminal silyl ethers via
 three-component hemiaminal silylation.
;
_journal_issue                   38
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6890
_journal_page_last               6894
_journal_paper_doi               10.1039/c8ob02089b
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C24 H28 N4 O Si'
_chemical_formula_sum            'C24 H28 N4 O Si'
_chemical_formula_weight         416.59
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-03-20
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.02.02 svn.r3481 for OlexSys, GUI svn.r5480)
;
_audit_update_record
;
2018-04-08 deposited with the CCDC.
2018-09-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4816(8)
_cell_length_b                   12.2451(6)
_cell_length_c                   16.6439(9)
_cell_measurement_reflns_used    2418
_cell_measurement_temperature    292.64(10)
_cell_measurement_theta_max      25.1920
_cell_measurement_theta_min      3.7720
_cell_volume                     2340.0(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.64(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0528
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):
  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -53.00  85.00   1.00   12.00    --   15.98   0.00-180.00  138
  2  \w     35.00  64.00   1.00   12.00    --   15.98  77.00  60.00   29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0411726000
_diffrn_orient_matrix_UB_12      -0.0098049000
_diffrn_orient_matrix_UB_13      0.0309371000
_diffrn_orient_matrix_UB_21      0.0326444000
_diffrn_orient_matrix_UB_22      0.0335926000
_diffrn_orient_matrix_UB_23      0.0264300000
_diffrn_orient_matrix_UB_31      -0.0325245000
_diffrn_orient_matrix_UB_32      0.0461560000
_diffrn_orient_matrix_UB_33      -0.0126338000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6796
_diffrn_reflns_point_group_measured_fraction_full 0.735
_diffrn_reflns_point_group_measured_fraction_max 0.735
_diffrn_reflns_theta_full        24.979
_diffrn_reflns_theta_max         24.979
_diffrn_reflns_theta_min         3.451
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.182
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Flack x determined using 622 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3019
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0380
_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^)+(0.0451P)^2^+0.1166P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0850
_refine_ls_wR_factor_ref         0.0911
_reflns_Friedel_coverage         0.420
_reflns_Friedel_fraction_full    0.452
_reflns_Friedel_fraction_max     0.452
_reflns_number_gt                2441
_reflns_number_total             3019
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob02089b2.cif
_cod_data_source_block           cx-20180320
_cod_depositor_comments
'Adding full bibliography for 7156425--7156426.cif.'
_cod_database_code               7156425
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C1 O1 Si1 N1'
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.959
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C8(H8), C4(H4), C21(H21), C3(H3), C2(H2), C25(H25), C22(H22),
 C24(H24), C6(H6), C7(H7), C23(H23)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C17(H17A,H17B,H17C), C15(H15A,H15B,H15C), C19(H19A,H19B,
 H19C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              77438
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.420
_oxdiff_exptl_absorpt_empirical_full_min 0.626