Three Stereoisomers of a Novel and Selective μ-Opioid Analgesic
Ianelli, S.; Nardelli, M.; Fraire, C.; Grancini, G.; Napoletano, M.; Santangelo, F.; Acta Crystallographica Section C 51 (1995) 1675–1680; doi:10.1107/S0108270195001478

data_2003817
_publ_section_title
;
 Three Stereoisomers of a Novel and Selective \m-Opioid Analgesic
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1675
_journal_page_last               1680
_journal_paper_doi               10.1107/S0108270195001478
_journal_volume                  51
_journal_year                    1995
_chemical_compound_source
;
chemical synthesis
;
_chemical_formula_analytical     'C21 H33 Cl N2 O2'
_chemical_formula_sum            'C21 H33 Cl N2 O2'
_chemical_formula_weight         380.96
_chemical_melting_point          312.0(10)
_chemical_name_systematic
;
(1S)-2-[(1R,1'S)-bis(1-Methylpropyl)amino]-1-[(5S)-1-(2-chlorophenyl)
methyl-2-oxo-5-pyrrolidinyl]ethanol
;
_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                 108.16(1)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.627(2)
_cell_length_b                   7.298(2)
_cell_length_c                   11.527(2)
_cell_measurement_radiation      CuK\a~1~
_cell_measurement_reflns_used    30
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      36.64
_cell_measurement_theta_min      20.05
_cell_measurement_wavelength     1.5405620
_cell_volume                     1089.3(4)
_computing_cell_refinement       'LQPARM (Nardelli & Mangia,1984)'
_computing_data_collection       'local programs'
_computing_data_reduction        'local programs'
_computing_molecular_graphics
'ORTEP (Johnson, 1965); PLUTO (Motherwell & Clegg, 1978)'
_computing_publication_material
'PARST (Nardelli, 1983); PARSTCIF (Nardelli, 1991)'
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1994)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_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         'fine-focus sealed tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_sigmaI/netI    0.0429
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2336
_diffrn_reflns_reduction_process
;
standard
;
_diffrn_reflns_theta_max         70.08
_diffrn_reflns_theta_min         3.41
_diffrn_standards_decay_%        'within statistical fluctuation'
_diffrn_standards_interval_count 50
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    1.677
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
Tabular
;
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.11
_refine_diff_density_min         -0.17
_refine_ls_abs_structure_details 'Flack  (1983)'
_refine_ls_abs_structure_Flack   0.12(3)
_refine_ls_extinction_coef       0.0059(6)
_refine_ls_extinction_method     'SHELXL93 (Sheldrick, 1993)'
_refine_ls_goodness_of_fit_all   0.795
_refine_ls_goodness_of_fit_obs   0.997
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2239
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.795
_refine_ls_restrained_S_obs      0.996
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_obs          0.0369
_refine_ls_shift/esd_max         -0.006
_refine_ls_shift/esd_mean        0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(F~o~^2^)+(0.0495P)^2^]  where  P = (F~o~^2^+2F~c~^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0924
_refine_ls_wR_factor_obs         0.0831
_reflns_number_observed          1267
_reflns_number_total             2239
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            mu1165.cif
_cod_data_source_block           2c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '311-313 K' was changed to
'312.0(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 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value
'w=1/[\s^2^(F~o~^2^)+(0.0495P)^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^)+(0.0495P)^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               2003817