3-Hexanoyl-1-tosylindole. A Highly Stereospecific Preparation of 3-Alkyl-Substituted Indoles
Mohialdin-Khaffaf, S.; Persaud, K. C.; Pritchard, R. G.; Acta Crystallographica Section C 52 (1996) 2607–2609; doi:10.1107/S010827019600580X

data_2005479
_publ_section_title
;
 3-Hexanoyl-1-tosylindole. A Highly Stereospecific Preparation of
 3-Alkyl-Substituted Indoles
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2607
_journal_page_last               2609
_journal_paper_doi               10.1107/S010827019600580X
_journal_volume                  52
_journal_year                    1996
_chemical_formula_iupac          'C21 H23 N1 O3 S1'
_chemical_formula_sum            'C21 H23 N O3 S'
_chemical_formula_weight         369.47
_chemical_melting_point          365.0(10)
_chemical_name_common
;
3-hexanoyl-1-tosylindole
;
_chemical_name_systematic
;
3-hexanoyl-1-(p-methylphenylsulphonyl)indole
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.
_cell_angle_beta                 103.27(2)
_cell_angle_gamma                90.
_cell_formula_units_Z            4
_cell_length_a                   8.984(2)
_cell_length_b                   16.588(4)
_cell_length_c                   13.732(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.0
_cell_measurement_theta_min      7.3
_cell_volume                     1991.8(7)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;
MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1988)
;
_computing_data_reduction
'TEXSAN PROCESS (Molecular Structure Corporation, 1985)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL93. Literature survey: CSSR (1984)'
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Rigaku AFC-6S'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_sigmaI/netI    0.1140
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3388
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.96
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.253
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.078
_refine_ls_goodness_of_fit_obs   1.222
_refine_ls_hydrogen_treatment    'H atoms riding with U(H) =  1.2U~eq~(C)'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3129
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.258
_refine_ls_restrained_S_obs      1.222
_refine_ls_R_factor_all          0.2052
_refine_ls_R_factor_obs          0.0659
_refine_ls_shift/esd_max         0.003
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
;
calc w = 1/[\s^2^(F~o~^2^) + (0.1506P)^2^]
where P = (F~o~^2^ + 2F~c~^2^)/3
;
_refine_ls_wR_factor_all         0.3392
_refine_ls_wR_factor_obs         0.1973
_reflns_number_observed          1219
_reflns_number_total             3152
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            cf1004.cif
_cod_data_source_block           smk3d
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '364-366' was changed to '365.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1991.8(6)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C21 H23 N1 O3 S1'
_cod_database_code               2005479