2-Ethylthio-5-methyl-6,7,8,9,10,11,12,13,14,15-decahydrocyclododeca[<i>b</i>]indole: an unexpected product from the demethylation of an indole using Fujita's reagent
Ianelli, Sandra; Nardelli, Mario; Belletti, Daniele; Caubère, Caterine; Caubère, Paul; Jamart-Grégoire, Brigitte; Acta Crystallographica Section C 50 (1994) 1916–1919; doi:10.1107/S0108270194003100

data_2010314
_publ_section_title
;2-Ethylthio-5-methyl-6,7,8,9,10,11,12,13,14,15-decahydrocyclododeca[<i>b</i>]indole:
 an unexpected product from the demethylation of an indole using Fujita's
 reagent
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1916
_journal_page_last               1919
_journal_paper_doi               10.1107/S0108270194003100
_journal_volume                  50
_journal_year                    1994
_chemical_formula_analytical     'C21 H31 N S'
_chemical_formula_sum            'C21 H31 N S'
_chemical_formula_weight         329.54
_chemical_name_systematic
;
   2-ethylthio-5-methyl-cyclododeca-6,7,8,9,10,11,12,13,14,15-decahydro
   [b]indole,
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_cell_angle_alpha                90.
_cell_angle_beta                 95.11(2)
_cell_angle_gamma                90.
_cell_formula_units_Z            2
_cell_length_a                   13.183(5)
_cell_length_b                   7.831(2)
_cell_length_c                   9.213(4)
_cell_measurement_reflns_used    29
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      39
_cell_measurement_theta_min      19
_cell_volume                     947.3(6)
_computing_cell_refinement       'LQPARM (Nardelli & Mangia, 1984)'
_computing_data_collection       'local programs'
_computing_data_reduction        'local programs'
_computing_molecular_graphics    'ORTEP (Johnson, 1965)'
_computing_publication_material
;
 PARST (Nardelli, 1983); PARSTCIF (Nardelli, 1991)
;
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Siemens-AED diffractometer'
_diffrn_measurement_method       '\q-2\q scan'
_diffrn_radiation_monochromator  Ni-filter
_diffrn_radiation_source         'standard Cu anode'
_diffrn_radiation_type           'X-ray Cu K\a~1~'
_diffrn_radiation_wavelength     1.540562
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_sigmaI/netI    0.0450
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            2047
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_max         70.1
_diffrn_reflns_theta_min         3.4
_diffrn_standards_decay_%        'within statistical fluctuation'
_diffrn_standards_interval_count 50
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    1.452
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.155
_exptl_crystal_description
;
small prisms
;
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.187
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_extinction_coef       0.0081(7)
_refine_ls_extinction_method
'F~c~^*^ = kF~c~[1 + 0.001xF~c~^2^\l^3^/sin(2\q)]^-1/4^'
_refine_ls_goodness_of_fit_all   0.949
_refine_ls_goodness_of_fit_obs   1.013
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         1941
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_restrained_S_obs      1.012
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_obs          0.0326
_refine_ls_shift/esd_max         0.033
_refine_ls_shift/esd_mean        0.005
_refine_ls_structure_factor_coef F^2^
_refine_ls_weighting_details
'w = 1/[\s^2^(F~o~^2^)+(0.0388P)^2^] where P = (F~o~^2^+2F~c~^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0920
_refine_ls_wR_factor_obs         0.0716
_reflns_number_observed          1394
_reflns_number_total             1943
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            li1099.cif
_cod_data_source_block           Y
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value ' calc w =
1/[\s^2^(F~o~^2^)+(0.0388P)^2^] where P = (F~o~^2^+2F~c~^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(F~o~^2^)+(0.0388P)^2^] where P = (F~o~^2^+2F~c~^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2010314