Reactions of Monoaryl-Substituted Methylenecyclobutanes and Methylenecyclopropanes with 1-Hydroxybenzotriazole (HOBt), 1-Hydroxy-7-azabenzotriazole (HOAt), and 1-Hydroxysuccinimide (HOSu)
Min Jiang; Min Shi; Journal of Organic Chemistry 74 (2009) 2516–2520; doi:10.1021/jo9000299

data_4024421
_publ_section_title
;
Reactions of Monoaryl-Substituted Methylenecyclobutanes and
Methylenecyclopropanes with 1-Hydroxybenzotriazole (HOBt),
1-Hydroxy-7-azabenzotriazole (HOAt), and 1-Hydroxysuccinimide (HOSu)
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2516
_journal_page_last               2520
_journal_paper_doi               10.1021/jo9000299
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C17 H14 Br N3 O2'
_chemical_formula_weight         372.22
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 90.417(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.8939(10)
_cell_length_b                   10.3365(18)
_cell_length_c                   26.251(5)
_cell_measurement_reflns_used    1433
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      38.726
_cell_measurement_theta_min      5.016
_cell_volume                     1599.2(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.1217
_diffrn_reflns_av_sigmaI/netI    0.1300
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9101
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.55
_exptl_absorpt_coefficient_mu    2.583
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7563
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.256
_exptl_crystal_size_mid          0.113
_exptl_crystal_size_min          0.079
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.126
_refine_ls_extinction_coef       0.0023(4)
_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   0.823
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3469
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.823
_refine_ls_R_factor_all          0.1200
_refine_ls_R_factor_gt           0.0527
_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^)+(0.0654P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1172
_refine_ls_wR_factor_ref         0.1552
_reflns_number_gt                1523
_reflns_number_total             3469
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9000299_si_001.cif
_cod_data_source_block           cd27564
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4024421