Synthesis of bicyclic vinyl triazenes by Ficini-type reactions.
Bormann, Carl Thomas; Fadaei-Tirani, Farzaneh; Scopelliti, Rosario; Severin, Kay; Organic & biomolecular chemistry 19 (2021) 8113–8117; doi:10.1039/d1ob01546j

data_7158295
_publ_section_title
;
 Synthesis of bicyclic vinyl triazenes by Ficini-type reactions.
;
_journal_issue                   37
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8113
_journal_page_last               8117
_journal_paper_doi               10.1039/d1ob01546j
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C20 H27 N3 O'
_chemical_formula_sum            'C20 H27 N3 O'
_chemical_formula_weight         325.44
_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     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-01-05
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-08-03 deposited with the CCDC.	2021-09-02 downloaded from the CCDC.
;
_cell_angle_alpha                69.946(8)
_cell_angle_beta                 72.758(6)
_cell_angle_gamma                64.698(8)
_cell_formula_units_Z            4
_cell_length_a                   10.9301(7)
_cell_length_b                   12.0124(11)
_cell_length_c                   16.8138(12)
_cell_measurement_reflns_used    5974
_cell_measurement_temperature    140.15
_cell_measurement_theta_max      72.6870
_cell_measurement_theta_min      4.9260
_cell_volume                     1845.4(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      140.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2817
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.971
_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    -31.00  -4.00   1.00    3.00    --  -40.91  70.00 133.00   27
  2  \w   -114.00 -10.00   1.00    3.00    --  -40.91 -70.00   1.00  104
  3  \w     36.00 100.00   1.00    3.00    --   40.91  70.00 133.00   64
  4  \w     -5.00  20.00   1.00    3.00    --   40.91 -70.00   1.00   25
  5  \w     91.00 124.00   1.00   12.00    --  105.15 -70.00   1.00   33
  6  \w     74.00 173.00   1.00   12.00    --  105.15  70.00 133.00   99
  7  \w    -20.00  71.00   1.00    3.00    --   40.91 -77.00-120.00   91
  8  \w     26.00 111.00   1.00    3.00    --   40.91  57.00  60.00   85
  9  \w     17.00  51.00   1.00    3.00    --   40.91  38.00 -90.00   34
 10  \w     36.00  80.00   1.00    3.00    --   40.91-125.00-180.00   44
 11  \w     69.00 113.00   1.00    3.00    --   40.91  38.00 -90.00   44
 12  \w     30.00 107.00   1.00   12.00    --  105.15-111.00 -90.00   77
 13  \w     29.00 109.00   1.00   12.00    --  105.15-111.00   0.00   80
 14  \w     48.00 107.00   1.00   12.00    --  105.15-111.00-180.00   59
 15  \w     81.00 106.00   1.00   12.00    --  105.15 -94.00  60.00   25
 16  \w     25.00  63.00   1.00   12.00    --  105.15 -94.00  60.00   38
 17  \w     72.00 130.00   1.00   12.00    --  105.15 178.00 -60.00   58
 18  \w    153.00 178.00   1.00   12.00    --  105.15  77.00-120.00   25
 19  \w    105.00 165.00   1.00   12.00    --  105.15 111.00  30.00   60
 20  \w     30.00 101.00   1.00   12.00    --  105.15 -94.00  30.00   71
 21  \w     80.00 178.00   1.00   12.00    --  105.15  45.00  90.00   98
 22  \w     79.00 163.00   1.00   12.00    --  105.15  30.00-150.00   84
 23  \w     39.00  81.00   1.00   12.00    --  105.15-111.00 -30.00   42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0206574000
_diffrn_orient_matrix_UB_12      -0.1173709000
_diffrn_orient_matrix_UB_13      -0.0277573000
_diffrn_orient_matrix_UB_21      0.1197281000
_diffrn_orient_matrix_UB_22      0.0219442000
_diffrn_orient_matrix_UB_23      -0.0715465000
_diffrn_orient_matrix_UB_31      0.1016129000
_diffrn_orient_matrix_UB_32      -0.0849228000
_diffrn_orient_matrix_UB_33      0.0626901000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7640
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.866
_diffrn_reflns_theta_min         2.842
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.572
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.453
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear pale colourless'
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_description       prism
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.461
_exptl_crystal_size_mid          0.168
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.512
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     442
_refine_ls_number_reflns         7640
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0883
_refine_ls_R_factor_gt           0.0810
_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^)+(0.1697P)^2^+0.9442P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2450
_refine_ls_wR_factor_ref         0.2503
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6257
_reflns_number_total             7640
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by 179.3084\% 
around [-0.01 -0.32 0.95] (reciprocal) or [-0.01 -0.70 0.72] (direct)
;
_cod_data_source_file            d1ob01546j2.cif
_cod_data_source_block           cb590-2
_cod_depositor_comments
'Adding full bibliography for 7158295--7158296.cif.'
_cod_database_code               7158295
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C20 H27 N3 O1'
_shelx_estimated_absorpt_t_max   0.935
_shelx_estimated_absorpt_t_min   0.778
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.628(3)
 0.372(3)
2. 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
3.a Ternary CH refined with riding coordinates:
 C1(H1), C4(H4), C8(H8), C12(H12), C21(H21), C24(H24), C28(H28), C32(H32)
3.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C29(H29A,H29B), C30(H30A,H30B),
 C31(H31A,H31B)
3.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C36(H36), C37(H37),
 C38(H38), C39(H39), C40(H40)
3.d Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C22(H22A,
 H22B,H22C), C23(H23A,H23B,H23C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C)
;
_shelx_res_checksum              43924
_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 1.825
_oxdiff_exptl_absorpt_empirical_full_min 0.431
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2