Design, synthesis and crystallographic study of novel indole-based cyano derivatives as key building blocks for heteropolycyclic compounds of major complexity.
García, Andrés C; Abonía, Rodrigo; Jaramillo-Gómez, Luz M; Cobo, Justo; Glidewell, Christopher; Acta crystallographica. Section C, Structural chemistry 73 (2017) 1040–1049; doi:10.1107/S2053229617015789

data_2311951
_publ_section_title
;
 Design, synthesis and crystallographic study of novel indole-based cyano
 derivatives as key building blocks for heteropolycyclic compounds of
 major complexity.
;
_journal_coeditor_code           YF3130
_journal_issue                   'Pt 12'
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_page_first              1040
_journal_page_last               1049
_journal_paper_doi               10.1107/S2053229617015789
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C19 H15 Br N2 O'
_chemical_formula_moiety         'C19 H15 Br N2 O'
_chemical_formula_sum            'C19 H15 Br N2 O'
_chemical_formula_weight         367.24
_chemical_name_systematic
;
(2<i>RS</i>)-2-(2-Bromobenzyl)-3-(1-methyl-1<i>H</i>-indol-3-yl)-\
3-oxopropanenitrile
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 92.165(19)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.728(6)
_cell_length_b                   14.901(6)
_cell_length_c                   15.507(6)
_cell_measurement_reflns_used    7297
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.576
_cell_measurement_theta_min      2.377
_cell_volume                     3170(2)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR92 (Altomare <i>et al.</i>,  1994)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0898
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            79963
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.576
_diffrn_reflns_theta_min         2.377
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.599
_exptl_absorpt_correction_T_max  0.771
_exptl_absorpt_correction_T_min  0.489
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            yellow-brown
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_description       plate
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.404
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
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_refine_diff_density_min         -0.762
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         7297
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0341
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0217P)^2^+3.7392P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0633
_refine_ls_wR_factor_ref         0.0721
_reflns_number_gt                5456
_reflns_number_total             7297
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            yf3130sup1.cif
_cod_data_source_block           IIb
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2311951
_shelx_estimated_absorpt_t_min   0.420
_shelx_estimated_absorpt_t_max   0.781
_shelx_hkl_checksum              66127
_shelx_res_checksum              33833
_shelxl_version_number           2.014