A formal [4 + 4] complementary ambiphile pairing reaction: a new cyclization pathway for ortho-quinone methides.
Samarakoon, Thiwanka B.; Hur, Moon Y.; Kurtz, Ryan D.; Hanson, Paul R.; Organic letters 12 (2010) 2182–2185; doi:10.1021/ol100495w

data_1502940
_publ_section_title
;
 A formal [4 + 4] complementary ambiphile pairing reaction: a new
 cyclization pathway for ortho-quinone methides.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2182
_journal_page_last               2185
_journal_paper_doi               10.1021/ol100495w
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C16 H14 Br N O3 S'
_chemical_formula_weight         380.25
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 100.217(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.252(2)
_cell_length_b                   7.4707(15)
_cell_length_c                   20.115(4)
_cell_measurement_reflns_used    1432
_cell_measurement_temperature    100(2)
_cell_volume                     1516.2(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX II CCD detector'
_diffrn_measurement_method       'w scans'
_diffrn_radiation_monochromator  'Quazar MX Optics'
_diffrn_radiation_source         'Bruker IuS microfocus'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_sigmaI/netI    0.0219
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            17720
_diffrn_reflns_theta_full        65.21
_diffrn_reflns_theta_max         65.21
_diffrn_reflns_theta_min         4.47
_diffrn_standards_decay_%        0.00
_exptl_absorpt_coefficient_mu    5.092
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.666
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.375
_refine_diff_density_min         -0.515
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         2527
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0366
_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^)+(0.0428P)^2^+2.8282P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.0914
_reflns_number_gt                2432
_reflns_number_total             2527
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol100495w_si_002.cif
_cod_data_source_block           k76h
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1502940