One-Pot Regioselective Synthesis of meta-Terphenyls via [3 + 3] Annulation of Nitroallylic Acetates with Alkylidenemalononitriles.
Gopi, Elumalai; Namboothiri, Irishi N. N.; The Journal of organic chemistry 79 (2014) 7468–7476; doi:10.1021/jo501193h

data_4029829
_publ_section_title
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 One-Pot Regioselective Synthesis of meta-Terphenyls via [3 + 3]
 Annulation of Nitroallylic Acetates with Alkylidenemalononitriles.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7468
_journal_page_last               7476
_journal_paper_doi               10.1021/jo501193h
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C20 H14 Br N O3'
_chemical_formula_sum            'C20 H14 Br N O3'
_chemical_formula_weight         396.23
_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                 97.206(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.446(3)
_cell_length_b                   7.600(3)
_cell_length_c                   29.561(11)
_cell_measurement_reflns_used    2203
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.3
_cell_measurement_theta_min      3.0
_cell_volume                     1659.6(11)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)'
_computing_data_reduction        'Bruker SAINT, SADABS and XPREP'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_source         MicroMax003_Mo
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0752
_diffrn_reflns_av_sigmaI/netI    0.0739
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            11437
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         3.02
_exptl_absorpt_coefficient_mu    2.496
_exptl_absorpt_correction_T_max  0.7709
_exptl_absorpt_correction_T_min  0.5214
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.883
_refine_diff_density_min         -0.575
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3001
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0403
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0367P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.0920
_reflns_number_gt                2261
_reflns_number_total             3001
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo501193h_si_002.cif
_cod_data_source_block           gopi
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 4029829.cif.
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_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4029829