Absolute configuration of <i>N</i>-[(–)-2-(7-methoxy-1,2,3,4-tetrahydro-1-naphthyl)ethyl]cyclopropylcarboxamide, a highly potent and selective melatonin analogue
Abdelhalim, Guelzim; Belloli, Emmanuelle; Yous, Said; Vaccher, Claude; Acta Crystallographica Section C 57 (2001) 100–101; doi:10.1107/S0108270100014724

data_2011720
_publ_section_title
;Absolute configuration of
 <i>N</i>-[(--)-2-(7-methoxy-1,2,3,4-tetrahydro-1-naphthyl)ethyl]cyclopropylcarboxamide,
 a highly potent and selective melatonin analogue
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              100
_journal_page_last               101
_journal_paper_doi               10.1107/S0108270100014724
_journal_volume                  57
_journal_year                    2001
_chemical_formula_moiety         'C17 H23 N  O2'
_chemical_formula_sum            'C17 H23 N O2'
_chemical_formula_weight         273.36
_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'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 95.262(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.6653(6)
_cell_length_b                   5.0767(4)
_cell_length_c                   22.615(2)
_cell_measurement_reflns_used    5338
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.26
_cell_measurement_theta_min      4.41
_cell_volume                     762.02(11)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_measured_fraction_theta_full .995
_diffrn_measured_fraction_theta_max .995
_diffrn_measurement_device_type  'Bruker SMART-CCD diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .023
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            9999
_diffrn_reflns_theta_full        25.26
_diffrn_reflns_theta_max         25.26
_diffrn_reflns_theta_min         2.71
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    .077
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             296
_exptl_crystal_size_max          .20
_exptl_crystal_size_mid          .18
_exptl_crystal_size_min          .08
_refine_diff_density_max         .177
_refine_diff_density_min         -.161
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   .01(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2673
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          .0392
_refine_ls_R_factor_gt           .0360
_refine_ls_shift/su_max          .001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0703P)^2^+0.0399P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1069
_reflns_number_gt                2422
_reflns_number_total             2673
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            gs1106.cif
_cod_data_source_block           IV
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        762.0(2)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2011720