Photoinduced, strain-promoted cycloadditions of trans-cycloheptenones and azides
Yang, Hongzhi; Zeng, Tianying; Xi, Shuang; Hu, Shengkun; Wu, Yunfei; Tang, Yefeng; Green Chemistry 22 (2020) 7023–7030; doi:10.1039/D0GC02347G

data_7241345
_publ_section_title
;
 Photoinduced, strain-promoted cycloadditions of trans-cycloheptenones and
 azides
;
_journal_issue                   20
_journal_name_full               'Green Chemistry'
_journal_page_first              7023
_journal_page_last               7030
_journal_paper_doi               10.1039/D0GC02347G
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         'C20 H44 Li2 N2 O4'
_chemical_formula_sum            'C20 H44 Li2 N2 O4'
_chemical_formula_weight         390.45
_chemical_name_systematic        lithiumdimethylamide
_chemical_properties_physical
Air-sensitive,Moisture-sensitive,Oxygen-sensitive,Pyrophoric
_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
_audit_creation_date             2020-06-30
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_audit_update_record
;
2020-07-01 deposited with the CCDC.	2020-10-01 downloaded from the CCDC.
;
_cell_angle_alpha                88.833(11)
_cell_angle_beta                 68.333(11)
_cell_angle_gamma                89.254(10)
_cell_formula_units_Z            1
_cell_length_a                   8.1303(9)
_cell_length_b                   8.5936(11)
_cell_length_c                   9.2306(12)
_cell_measurement_reflns_used    1893
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      28.6340
_cell_measurement_theta_min      3.5210
_cell_volume                     599.23(14)
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.15
_diffrn_detector                 Sapphire
_diffrn_detector_area_resol_mean 16.0560
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Oxford Xcalibur'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  grahpite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4307
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.998
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         2.371
_diffrn_source                   'microfocus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.082
_exptl_crystal_description       plate
_exptl_crystal_F_000             216
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: thf, n-pentane'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.920
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         4307
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.920
_refine_ls_R_factor_all          0.0926
_refine_ls_R_factor_gt           0.0589
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1195P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1658
_refine_ls_wR_factor_ref         0.1789
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2521
_reflns_number_total             4307
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0gc02347g2.cif
_cod_data_source_block           3203hklf4
_cod_depositor_comments
'Adding full bibliography for 7241345--7241346.cif.'
_cod_database_code               7241345
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.986
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.8959(10)
 0.1041(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Others
 Sof(H6BC)=Sof(H6BD)=Sof(C7B)=Sof(H7BA)=Sof(H7BB)=Sof(H8BC)=Sof(H8BD)=1-FVAR(1)
 Sof(H6AA)=Sof(H6AB)=Sof(C7A)=Sof(H7AA)=Sof(H7AB)=Sof(H8AA)=Sof(H8AB)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6AA,
 H6AB), C6(H6BC,H6BD), C7A(H7AA,H7AB), C7B(H7BA,H7BB), C8(H8AA,H8AB), C8(H8BC,
 H8BD)
4.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_shelx_res_checksum              70665
_olex2_submission_special_instructions 'No special instructions were received'