Synthesis and intramolecular ring transformation of N,N′-dialkylated 2,6,9-triazabicyclo[3.3.1]nonadienes
Nakaike, Yumi; Yoshida, Yusuke; Yokoyama, Soichi; Ito, Akitaka; Nishiwaki, Nagatoshi; Organic & Biomolecular Chemistry 18 (2020) 9109–9116; doi:10.1039/D0OB01950J

data_7157748
_publ_section_title
;
 Synthesis and intramolecular ring transformation of
 N,N&#x2032;-dialkylated 2,6,9-triazabicyclo[3.3.1]nonadienes
;
_journal_issue                   44
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              9109
_journal_page_last               9116
_journal_paper_doi               10.1039/D0OB01950J
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C20 H19 N5 O4'
_chemical_formula_sum            'C20 H19 N5 O4'
_chemical_formula_weight         393.40
_chemical_name_systematic        KUTYY-29bicycloBn
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-09-07
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2020-09-07 deposited with the CCDC.	2020-10-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 140.02(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.4032(16)
_cell_length_b                   9.8582(2)
_cell_length_c                   19.916(2)
_cell_measurement_reflns_used    7839
_cell_measurement_temperature    93.15
_cell_measurement_theta_max      29.4150
_cell_measurement_theta_min      2.0810
_cell_volume                     1817.0(8)
_computing_cell_refinement       'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      93.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -19.00  18.00   0.50    0.75    --   12.56 -84.00  67.00   74
  2  \w    -51.00  33.00   0.50    0.75    --  -13.19  84.00-172.00  168
  3  \w    -41.00  11.00   0.50    0.75    --  -13.19 -84.00  67.00  104
  4  \w     43.00  95.00   0.50    0.75    --   12.56 178.00  30.00  104
  5  \w     32.00  58.00   0.50    0.75    --   12.56 -99.00 -30.00   52
  6  \w    -21.00   7.00   0.50    0.75    --   12.56 -99.00 -30.00   56
  7  \w     29.00  62.00   0.50    0.75    --  -13.19  57.00-150.00   66
  8  \w    -18.00   7.00   0.50    0.75    --  -13.19 -99.00   0.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0383338000
_diffrn_orient_matrix_UB_12      0.0389060000
_diffrn_orient_matrix_UB_13      0.0028519000
_diffrn_orient_matrix_UB_21      0.0144884000
_diffrn_orient_matrix_UB_22      -0.0499615000
_diffrn_orient_matrix_UB_23      0.0327659000
_diffrn_orient_matrix_UB_31      0.0647598000
_diffrn_orient_matrix_UB_32      0.0341646000
_diffrn_orient_matrix_UB_33      0.0446114000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13775
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.505
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.141
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.47a (Rigaku Oxford Diffraction, 2019)
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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.796
_exptl_crystal_size_mid          0.532
_exptl_crystal_size_min          0.413
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0089(9)
_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   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3711
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0351
_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^)+(0.0376P)^2^+0.7655P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0892
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3308
_reflns_number_total             3711
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01950j2.cif
_cod_data_source_block           331bicyclo-bn_1
_cod_original_cell_volume        1817.0(6)
_cod_database_code               7157748
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C84 H72 N16 O16 '
_diffrn_oxdiff_digest_frames
;
018612716535303438e226bcc075b0c9540067411be
;
_diffrn_oxdiff_digest_hkl
;
01caa2c90eeee073f53e5c657f8ce707435be4
;
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C00B(H00C), C00C(H00D)
2.b Secondary CH2 refined with riding coordinates:
 C00A(H00A,H00B), C00I(H00G,H00I)
2.c Aromatic/amide H refined with riding coordinates:
 N008(H008), C00E(H00E), C00F(H00F), C00H(H00H), C00J(H00J), C00L(H00L),
 C00M(H00M), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S),
 C00T(H00T)
;
_shelx_res_checksum              75552
_olex2_date_sample_data_collection 2019-11-07
_olex2_submission_original_sample_id KUTYY-29bicycloBn
_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 1.092
_oxdiff_exptl_absorpt_empirical_full_min 0.927