Synthesis of highly functionalized 2-thiaspiro[4.5]deca-6,8-dienes via atom efficient tandem Michael addition/Thorpe-Ziegler cyclization
Anusha Rani, Mani; Vivek Kumar, Sundaravel; Roja, Somi; Almansour, Abdulrahman Ibrahim; Kumar, Raju; Athimoolam, S.; Raju, Ranjith Kumar; RSC Adv.  (2016) –; doi:10.1039/C6RA05572A

data_7224943
_publ_section_title
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 Synthesis of highly functionalized 2-thiaspiro[4.5]deca-6,8-dienes via
 atom efficient tandem Michael addition/Thorpe-Ziegler cyclization
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_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA05572A
_journal_year                    2016
_chemical_formula_moiety         'C30 H22 Br2 N2 O S'
_chemical_formula_sum            'C30 H22 Br2 N2 O S'
_chemical_formula_weight         618.37
_chemical_melting_point          224
_chemical_name_common
(Z)-6-Amino-3-(2-bromobenzylidene)-10-(2-bromophenyl)-4-oxo-8-(p-tolyl)-2-thiaspiro[4.5]deca-6,8-diene-7-carbonitrile
_chemical_name_systematic
(Z)-6-Amino-3-(2-bromobenzylidene)-10-(2-bromophenyl)-4-oxo-8-(p-tolyl)-2-thiaspiro[4.5]deca-6,8-diene-7-carbonitrile
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2016-02-27 deposited with the CCDC.
2016-04-15 downloaded from the CCDC.
;
_cell_angle_alpha                76.797(9)
_cell_angle_beta                 83.778(8)
_cell_angle_gamma                77.976(6)
_cell_formula_units_Z            2
_cell_length_a                   7.8301(4)
_cell_length_b                   9.9382(6)
_cell_length_c                   18.0845(11)
_cell_measurement_reflns_used    3216
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.58
_cell_measurement_theta_min      2.16
_cell_volume                     1337.29(14)
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       \w
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            25914
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.144
_exptl_absorpt_coefficient_mu    3.135
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             620
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4709
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0288
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0366P)^2^+0.7025P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0708
_refine_ls_wR_factor_ref         0.0736
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3850
_reflns_number_total             4709
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra05572a2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_original_cell_volume        1337.29(15)
_cod_database_code               7224943
_shelxl_version_number           2014-3
_shelx_res_checksum              93405