The effect of hydrogen bonding on the conformations of 2-(1<i>H</i>-indol-3-yl)-2-oxoacetamide and 2-(1<i>H</i>-indol-3-yl)-<i>N</i>,<i>N</i>-dimethyl-2-oxoacetamide
Sonar, Vijayakumar N.; Parkin, Sean; Crooks, Peter A.; Acta Crystallographica Section C 68 (2012) o405–o407; doi:10.1107/S0108270112038322

data_2018696
_publ_section_title
;
 The effect of hydrogen bonding on the conformations of
 2-(1<i>H</i>-indol-3-yl)-2-oxoacetamide and
 2-(1<i>H</i>-indol-3-yl)-<i>N</i>,<i>N</i>-dimethyl-2-oxoacetamide
;
_journal_coeditor_code           YP3017
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o405
_journal_page_last               o407
_journal_paper_doi               10.1107/S0108270112038322
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C10 H8 N2 O2'
_chemical_formula_moiety         'C10 H8 N2 O2'
_chemical_formula_sum            'C10 H8 N2 O2'
_chemical_formula_weight         188.18
_chemical_name_systematic
;
2-(1<i>H</i>-indol-3-yl)-2-oxoacetamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.251(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.1253(4)
_cell_length_b                   19.4363(14)
_cell_length_c                   8.4953(6)
_cell_measurement_reflns_used    8721
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      68.95
_cell_measurement_theta_min      4.55
_cell_volume                     844.91(11)
_computing_cell_refinement       'APEX2 (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'APEX2 (Bruker, 2006)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and local procedures
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90.0(2)
_diffrn_detector_area_resol_mean 18
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker X8 Proteum'
_diffrn_measurement_method       '\f and \w'
_diffrn_radiation_monochromator  'graded multilayer optics'
_diffrn_radiation_source         'fine-focus rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_sigmaI/netI    0.0286
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10887
_diffrn_reflns_theta_full        68.94
_diffrn_reflns_theta_max         68.94
_diffrn_reflns_theta_min         4.55
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.880
_exptl_absorpt_correction_T_max  0.949
_exptl_absorpt_correction_T_min  0.744
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[SADABS (Bruker, 2006) and XABS2 (Parkin <i>et al.</i>, 1995)]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.330
_refine_ls_extinction_coef       0.0033(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.235
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1518
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.235
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0575
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0370P)^2^+1.8838P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1576
_refine_ls_wR_factor_ref         0.1581
_reflns_number_gt                1481
_reflns_number_total             1518
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            yp3017.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2018696
_cod_database_fobs_code          2018696