Rapid access to N-(indol-2-yl)amides and N-(indol-3-yl)amides as unexplored pharmacophores.
Reekie, Tristan A.; Wilkinson, Shane M.; Law, Vivian; Hibbs, David E.; Ong, Jennifer A.; Kassiou, Michael; Organic & biomolecular chemistry 15 (2017) 576–580; doi:10.1039/c6ob02622b

data_7155419
_publ_section_title
;
 Rapid access to N-(indol-2-yl)amides and N-(indol-3-yl)amides as
 unexplored pharmacophores.
;
_journal_issue                   3
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              576
_journal_page_last               580
_journal_paper_doi               10.1039/c6ob02622b
_journal_volume                  15
_journal_year                    2017
_chemical_formula_moiety         'C17 H15 N3 O3'
_chemical_formula_sum            'C17 H15 N3 O3'
_chemical_formula_weight         309.32
_chemical_name_systematic
N-(1-methyl-1H-indol-3-yl)-2-(4-nitrophenyl)acetamide
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2013-10-10
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_audit_update_record
;
2016-10-05 deposited with the CCDC.
2016-12-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.133(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.7845(14)
_cell_length_b                   7.017(2)
_cell_length_c                   21.720(6)
_cell_measurement_reflns_used    110
_cell_measurement_temperature    150
_cell_measurement_theta_max      25.284
_cell_measurement_theta_min      1.876
_cell_volume                     728.7(4)
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      150.15
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX2'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            4556
_diffrn_reflns_point_group_measured_fraction_full 0.871
_diffrn_reflns_point_group_measured_fraction_max 0.865
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.684
_diffrn_reflns_theta_min         1.876
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6533
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_description       needle
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 668 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.4(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         2409
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0395
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0301P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0674
_refine_ls_wR_factor_ref         0.0754
_reflns_Friedel_coverage         0.736
_reflns_Friedel_fraction_full    0.747
_reflns_Friedel_fraction_max     0.735
_reflns_number_gt                1868
_reflns_number_total             2409
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob02622b2.cif
_cod_data_source_block           13sw005_nc
_cod_depositor_comments          'Adding full bibliography for 7155419.cif.'
_cod_database_code               7155419
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.976
_shelxl_version_number           2013-4