TiCl4 Promoted Formal [3 + 3] Cycloaddition of Cyclopropane 1,1-Diesters with Azides: Synthesis of Highly Functionalized Triazinines and Azetidines.
Zhang, Huan-Huan; Luo, Yong-Chun; Wang, Hua-Peng; Chen, Wei; Xu, Peng-Fei; Organic letters 16 (2014) 4896–4899; doi:10.1021/ol5024079

data_1517566
_publ_section_title
;
 TiCl4 Promoted Formal [3 + 3] Cycloaddition of Cyclopropane 1,1-Diesters
 with Azides: Synthesis of Highly Functionalized Triazinines and
 Azetidines.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4896
_journal_page_last               4899
_journal_paper_doi               10.1021/ol5024079
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C21 H23 N3 O5'
_chemical_formula_sum            'C21 H23 N3 O5'
_chemical_formula_weight         397.42
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-03-01
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 97.583(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.5617(4)
_cell_length_b                   9.5319(3)
_cell_length_c                   14.8718(4)
_cell_measurement_reflns_used    2805
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.8460
_cell_measurement_theta_min      3.6560
_cell_volume                     2046.16(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9903
_diffrn_measured_fraction_theta_max 0.8736
_diffrn_measurement_details
;
  1 omega  -11.00   15.40   1.2000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.1930  -99.0000 -150.0000 22

  2 omega  -46.00   45.20   1.2000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305  -57.0000   60.0000 76

  3 omega   -1.00   92.60   1.2000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305   57.0000 -150.0000 78

  4 omega   37.00   63.40   1.2000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305   19.0000   90.0000 22
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0054920000
_diffrn_orient_matrix_UB_12      -0.0738215000
_diffrn_orient_matrix_UB_13      -0.0034763000
_diffrn_orient_matrix_UB_21      -0.0292136000
_diffrn_orient_matrix_UB_22      0.0085013000
_diffrn_orient_matrix_UB_23      -0.0417577000
_diffrn_orient_matrix_UB_31      0.0391267000
_diffrn_orient_matrix_UB_32      -0.0040253000
_diffrn_orient_matrix_UB_33      -0.0236860000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8062
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.00
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89576
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.023(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4139
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0539
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1592
_refine_ls_wR_factor_ref         0.1860
_reflns_number_gt                2861
_reflns_number_total             4139
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5024079_si_003.cif
_cod_data_source_block           luoych0226
_cod_depositor_comments          'Adding full bibliography for 1517566.cif.'
_cod_original_cell_volume        2046.17(11)
_cod_database_code               1517566
_reflns_odcompleteness_completeness 99.03
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H4 of C4, H5 of C5, {H7A,H7B} of C7, H8 of C8, {H9A,H9B} of C9, H17 of C17,
  H18 of C18, H1 of C1, H2 of C2, H3 of C3, H19 of C19, H20 of C20
 At 1.5 times of:
  {H12A,H12B,H12C} of C12, {H14A,H14B,H14C} of C14, {H21A,H21B,H21C} of C21
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C17(H17), C18(H18), C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C21(H21A,H21B,H21C)
;