Difluorobenzocyclooctyne: Synthesis, Reactivity, and Stabilization by β-Cyclodextrin
Ellen M. Sletten; Hitomi Nakamura; John C. Jewett; Carolyn R. Bertozzi; Journal of the American Chemical Society 132 (2010) 11799–11805; doi:10.1021/ja105005t

data_4102926
_publ_section_title
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 Difluorobenzocyclooctyne: Synthesis, Reactivity, and Stabilization by
 \b-Cyclodextrin
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11799
_journal_page_last               11805
_journal_paper_doi               10.1021/ja105005t
_journal_volume                  132
_journal_year                    2010
_chemical_formula_sum            'C36 H30 F6'
_chemical_formula_weight         576.60
_chemical_name_common            EMS-VIII-007D
_chemical_name_systematic
;
 bertozzi01
;
_space_group.centring_type       P
_space_group_IT_number           4
_space_group.IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 103.344(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.0552(4)
_cell_length_b                   12.8869(6)
_cell_length_c                   12.0073(5)
_cell_measurement_reflns_used    9930
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.91
_cell_measurement_theta_min      3.78
_cell_volume                     1363.34(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  SHELXL-97
_computing_structure_solution    SIR-2008
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'HELIOS multilayer mirrors'
_diffrn_radiation_source         'microfocus rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0149
_diffrn_reflns_av_sigmaI/netI    0.0158
_diffrn_refln_scan_rate          5
_diffrn_refln_scan_width         1.0
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12405
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         68.17
_diffrn_reflns_theta_min         3.78
_exptl_absorpt_coefficient_mu    0.916
_exptl_absorpt_correction_T_max  0.9643
_exptl_absorpt_correction_T_min  0.8980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         4349
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0274
_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^)+(0.0462P)^2^+0.3189P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0735
_refine_ls_wR_factor_ref         0.0744
_reflns_number_gt                4259
_reflns_number_total             4349
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja105005t_si_002.cif
_cod_data_source_block           bertozzi01
_cod_depositor_comments
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The following automatic conversions were performed:

'_space_group.centring_type' value 'primitive' was replaced with the
value 'P' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5642 2017-10-24 12:04:52Z antanas 
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_cod_database_code               4102926