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_7158296
_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         'C26 H36 N4 O3 S'
_chemical_formula_sum            'C26 H36 N4 O3 S'
_chemical_formula_weight         484.65
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-05-07
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-08-03 deposited with the CCDC.	2021-09-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.7493(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.80574(8)
_cell_length_b                   34.1537(3)
_cell_length_c                   9.62710(9)
_cell_measurement_reflns_used    12502
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      72.5600
_cell_measurement_theta_min      4.7730
_cell_volume                     2553.63(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_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 2018/2 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2817
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_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    -89.00 -64.00   1.00    2.00    --  -40.91 155.00 -71.00   25
  2  \w   -111.00 -86.00   1.00    2.00    --  -40.91-155.00-110.00   25
  3  \w    -68.00 -43.00   1.00    2.00    --  -40.91 120.00 131.00   25
  4  \w     56.00  81.00   1.00    2.00    --   40.91-120.00  47.00   25
  5  \w     46.00  73.00   1.00    8.00    --  105.15-120.00  47.00   27
  6  \w     93.00 142.00   1.00    8.00    --  105.15 155.00 -71.00   49
  7  \w    120.00 146.00   1.00    8.00    --  105.15 120.00 131.00   26
  8  \w     64.00  89.00   1.00    8.00    --  105.15-155.00-110.00   25
  9  \w   -114.00 -17.00   1.00    2.00    --  -40.91 -38.00 -60.00   97
 10  \w    -86.00 -10.00   1.00    2.00    --  -40.91 125.00-180.00   76
 11  \w   -106.00 -16.00   1.00    2.00    --  -40.91 -38.00  30.00   90
 12  \w     49.00  74.00   1.00    2.00    --   40.91-125.00 -90.00   25
 13  \w    -21.00  50.00   1.00    2.00    --   40.91 -77.00 150.00   71
 14  \w    135.00 161.00   1.00    8.00    --  105.15 111.00-120.00   26
 15  \w     34.00  70.00   1.00    8.00    --  105.15-111.00 -60.00   36
 16  \w     80.00 178.00   1.00    8.00    --  105.15  45.00 120.00   98
 17  \w     29.00 109.00   1.00    8.00    --  105.15-111.00 120.00   80
 18  \w     31.00 130.00   1.00    8.00    --  105.15 -77.00 -60.00   99
 19  \w     23.00  98.00   1.00    8.00    --  105.15 -94.00-120.00   75
 20  \w     84.00 109.00   1.00    8.00    --  105.15-111.00 -60.00   25
 21  \w     57.00 108.00   1.00    8.00    --  105.15-111.00   0.00   51
 22  \w     43.00 109.00   1.00    8.00    --  105.15-111.00-180.00   66
 23  \w     82.00 178.00   1.00    8.00    --  105.15  30.00-180.00   96
 24  \w    104.00 144.00   1.00    8.00    --  105.15 111.00   0.00   40
 25  \w     76.00 176.00   1.00    8.00    --  105.15  61.00  60.00  100
;
_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      -0.1973596000
_diffrn_orient_matrix_UB_12      0.0007047000
_diffrn_orient_matrix_UB_13      -0.0001307000
_diffrn_orient_matrix_UB_21      0.0006201000
_diffrn_orient_matrix_UB_22      0.0447647000
_diffrn_orient_matrix_UB_23      -0.0196589000
_diffrn_orient_matrix_UB_31      -0.0198985000
_diffrn_orient_matrix_UB_32      -0.0055030000
_diffrn_orient_matrix_UB_33      -0.1596238000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            20995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.655
_diffrn_reflns_theta_min         4.795
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.400
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.640
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on Gaussian integration over
a multifaceted crystal model.
Empirical absorption correction using spherical harmonics
as implemented in SCALE3 ABSPACK scaling algorithm
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_description       plate
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.00059(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     314
_refine_ls_number_reflns         5004
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0310
_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^)+(0.0405P)^2^+0.9103P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0799
_refine_ls_wR_factor_ref         0.0816
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4698
_reflns_number_total             5004
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01546j2.cif
_cod_data_source_block           cb715-1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Gaussian' was
changed to 'gaussian' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/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 

 Adding full bibliography for 7158295--7158296.cif.
;
_cod_original_cell_volume        2553.62(4)
_cod_database_code               7158296
_shelx_shelxl_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_oxdiff_formula         'C26 H36 N4 O3 S'
_shelx_estimated_absorpt_t_max   0.959
_shelx_estimated_absorpt_t_min   0.712
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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
2.a Ternary CH refined with riding coordinates:
 C2(H2), C21(H21), C24(H24)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C15(H15), C16(H16), C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C20(H20A,H20B,H20C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C)
;
_shelx_res_checksum              79910
_olex2_date_sample_data_collection 2021-05-06
_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
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.338
_oxdiff_exptl_absorpt_empirical_full_min 0.764