One-Pot Synthesis of 2-(Het)aryl/alkyl-3-cyanobenzofurans from 2-(2-Bromoaryl)-3-(het)aryl-3-(methylthio)acrylonitriles and Benzyl Carbamate.
Saraiah, Bonagiri; Gautam, Vibha; Acharya, Anand; Pasha, Mohamed Afzal; Ila, Hiriyakkanavar; ACS omega 3 (2018) 8355–8364; doi:10.1021/acsomega.8b01172

data_4516076
_publ_section_title
;
 One-Pot Synthesis of 2-(Het)aryl/alkyl-3-cyanobenzofurans from
 2-(2-Bromoaryl)-3-(het)aryl-3-(methylthio)acrylonitriles and Benzyl
 Carbamate.
;
_journal_issue                   7
_journal_name_full               'ACS omega'
_journal_page_first              8355
_journal_page_last               8364
_journal_paper_doi               10.1021/acsomega.8b01172
_journal_volume                  3
_journal_year                    2018
_chemical_formula_moiety         'C16 H10 F N O2'
_chemical_formula_sum            'C16 H10 F N O2'
_chemical_formula_weight         267.25
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-02-29
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.01.19 svn.r3143 for OlexSys, GUI svn.r4992)
;
_cell_angle_alpha                87.5870(10)
_cell_angle_beta                 76.7180(10)
_cell_angle_gamma                67.6650(10)
_cell_formula_units_Z            2
_cell_length_a                   7.9674(2)
_cell_length_b                   8.6081(3)
_cell_length_c                   10.2555(3)
_cell_measurement_reflns_used    9997
_cell_measurement_temperature    299
_cell_measurement_theta_max      33.408
_cell_measurement_theta_min      2.841
_cell_volume                     632.40(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      299.25
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            29883
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         33.765
_diffrn_reflns_theta_min         2.841
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.7467
_exptl_absorpt_correction_T_min  0.6972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0785 before and 0.0479 after correction.
The Ratio of minimum to maximum transmission is 0.9337.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_description       block
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         4823
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.1023
_refine_ls_R_factor_gt           0.0598
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0673P)^2^+0.1419P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1402
_refine_ls_wR_factor_ref         0.1579
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3137
_reflns_number_total             4823
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao8b01172_si_002.cif
_cod_data_source_block           compound_7b
_cod_database_code               4516076
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00I(H00I),
 C00J(H00J)
2.b Idealised Me refined as rotating group:
 C00K(H00A,H00B,H00C)
;
_shelx_res_checksum              25337
_shelx_hkl_checksum              99303
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'