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_7157747
_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         'C12 H19 N5 O4'
_chemical_formula_sum            'C12 H19 N5 O4'
_chemical_formula_weight         297.32
_chemical_name_systematic        KUTYY-26bicycloPr
_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   mixed
_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                 105.159(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.8252(6)
_cell_length_b                   7.4804(2)
_cell_length_c                   10.9523(4)
_cell_measurement_reflns_used    7233
_cell_measurement_temperature    123.15
_cell_measurement_theta_max      30.0420
_cell_measurement_theta_min      2.3500
_cell_volume                     1409.56(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      123.15
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 1.000
_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    -13.00  13.00   0.50   32.49    --   12.40  88.00 -84.00   52
  2  \w    -22.00  11.00   0.50   32.49    --  -13.03  57.00-180.00   66
  3  \w    -53.00  43.00   0.50   32.49    --  -13.03  88.00 -84.00  192
  4  \w    -41.00  50.00   0.50   32.49    --   12.40 -88.00 159.00  182
  5  \w    -22.00  27.00   0.50   32.49    --  -13.03 -99.00   0.00   98
  6  \w    -97.00 -50.00   0.50   32.49    --  -13.03-178.00 -60.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-S'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0008564000
_diffrn_orient_matrix_UB_12      -0.0677688000
_diffrn_orient_matrix_UB_13      -0.0449692000
_diffrn_orient_matrix_UB_21      0.0246485000
_diffrn_orient_matrix_UB_22      -0.0523405000
_diffrn_orient_matrix_UB_23      0.0481149000
_diffrn_orient_matrix_UB_31      -0.0330102000
_diffrn_orient_matrix_UB_32      -0.0408378000
_diffrn_orient_matrix_UB_33      0.0128480000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10670
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.368
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              PhotonJet-S
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.775
_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    1.401
_exptl_crystal_description       needle
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.294
_exptl_crystal_size_mid          0.082
_exptl_crystal_size_min          0.033
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2885
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0343
_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^)+(0.0385P)^2^+0.5226P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.0871
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2478
_reflns_number_total             2885
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01950j2.cif
_cod_data_source_block           20190520_331bicyclopr_2
_cod_database_code               7157747
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C12 H19 N5 O4 '
_diffrn_oxdiff_digest_frames
;
019ef3b83a4f11bd2c3af873548cfad25d00684aed1
;
_diffrn_oxdiff_digest_hkl
;
015b837f9e9c8718566bfb35abc4795eb7cae1
;
_reflns_odcompleteness_completeness 99.87
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N009(H009)
2.b Ternary CH refined with riding coordinates:
 C00D(H00D), C00E(H00E)
2.c Secondary CH2 refined with riding coordinates:
 C00G(H00B,H00C), C00H(H00G,H00H), C00I(H00I,H00J), C00J(H00K,H00L)
2.d Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00F(H00F)
2.e Idealised Me refined as rotating group:
 C00K(H00M,H00N,H00O), C00L(H00P,H00Q,H00R)
;
_olex2_date_sample_data_collection 2019-05-20
_olex2_submission_original_sample_id KUTYY-26bicycloPr
_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 1.084
_oxdiff_exptl_absorpt_empirical_full_min 0.815