One-step synthesis of polysubstituted benzene derivatives by multi-component cyclization of alpha-bromoacetate, malononitrile and aromatic aldehydes.
Yan, Chao Guo; Song, Xiao Kai; Wang, Qi Fang; Sun, Jing; Siemeling, Ulrich; Bruhn, Clemens; Chemical communications (Cambridge, England)  (2008) 1440–1442; doi:10.1039/b718171j

data_7102987
_publ_section_title
;
 One-step synthesis of polysubstituted benzene derivatives by
 multi-component cyclization of alpha-bromoacetate, malononitrile and
 aromatic aldehydes.
;
_journal_issue                   12
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1440
_journal_page_last               1442
_journal_paper_doi               10.1039/b718171j
_journal_year                    2008
_chemical_formula_moiety         'C14 H11 Br N2 O2'
_chemical_formula_sum            'C14 H11 Br N2 O2'
_chemical_formula_weight         319.16
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.198(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.0199(7)
_cell_length_b                   8.0123(5)
_cell_length_c                   24.381(2)
_cell_measurement_reflns_used    7781
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      25.55
_cell_measurement_theta_min      1.68
_cell_volume                     1365.7(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      133(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      ' 180 frames, detector distance = 135 mm'
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    '0.5 mm diameter, multiple pinhole'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1118
_diffrn_reflns_av_sigmaI/netI    0.0819
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            8536
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.68
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           32
_diffrn_source_power             1.60
_diffrn_source_voltage           50
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    3.009
_exptl_absorpt_correction_T_max  0.4988
_exptl_absorpt_correction_T_min  0.2908
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'X-red ver 1.06 (Stoe & Cie. 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.797
_refine_diff_density_min         -1.115
_refine_diff_density_rms         0.111
_refine_ls_extinction_coef       0.0031(12)
_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   0.947
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2385
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.947
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0415
_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^)+(0.0600P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1085
_reflns_number_gt                1887
_reflns_number_total             2385
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b718171j.txt
_cod_data_source_block           i0373
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7102987