Strain-promoted azide-alkyne cycloadditions of benzocyclononynes.
Tummatorn, Jumreang; Batsomboon, Paratchata; Clark, Ronald J.; Alabugin, Igor V.; Dudley, Gregory B.; The Journal of organic chemistry 77 (2012) 2093–2097; doi:10.1021/jo300188y

data_4037598
_publ_section_title
;
 Strain-promoted azide-alkyne cycloadditions of benzocyclononynes.
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_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2093
_journal_page_last               2097
_journal_paper_doi               10.1021/jo300188y
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C16 H20 O4'
_chemical_formula_weight         276.32
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 114.6350(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.1194(18)
_cell_length_b                   7.8260(11)
_cell_length_c                   14.852(2)
_cell_measurement_temperature    173(2)
_cell_volume                     1386.1(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14081
_diffrn_reflns_theta_full        27.19
_diffrn_reflns_theta_max         27.19
_diffrn_reflns_theta_min         2.71
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9932
_exptl_absorpt_correction_T_min  0.9869
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0002(16)
_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   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         3074
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0425
_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^)+(0.0620P)^2^+0.5388P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1147
_reflns_number_gt                2654
_reflns_number_total             3074
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300188y_si_003.cif
_cod_data_source_block           greg15
_cod_database_code               4037598