Rhodium-catalyzed chemo-, regio-, and enantioselective [2 + 2 + 2] cycloaddition of alkynes with isocyanates.
Tanaka, Ken; Wada, Azusa; Noguchi, Keiichi; Organic letters 7 (2005) 4737–4739; doi:10.1021/ol052041b

data_1556114
_publ_section_title
;
 Rhodium-catalyzed chemo-, regio-, and enantioselective [2 + 2 + 2]
 cycloaddition of alkynes with isocyanates.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              4737
_journal_page_last               4739
_journal_paper_doi               10.1021/ol052041b
_journal_volume                  7
_journal_year                    2005
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H20 Cl N O'
_chemical_formula_sum            'C18 H20 Cl N O'
_chemical_formula_weight         301.80
_chemical_melting_point          360.1(5)
_chemical_name_common
;
'(R)-(+)-2-Butyl-1-(2-chlorophenyl)-2,5,6,7-
tetrahydro[2]pyrindin-3-one'
;
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      1
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2005-06-03
_audit_creation_method           SHELXL-97
_cell_angle_alpha                106.260(7)
_cell_angle_beta                 92.413(8)
_cell_angle_gamma                114.734(7)
_cell_formula_units_Z            2
_cell_length_a                   9.0186(10)
_cell_length_b                   10.1685(11)
_cell_length_c                   10.3380(12)
_cell_measurement_reflns_used    14068
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      4.5
_cell_volume                     812.73(17)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_molecular_graphics
'ORTEP-3 for Windows Ver. 1.076 (Farrugia, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.067
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14989
_diffrn_reflns_theta_full        68.20
_diffrn_reflns_theta_max         68.20
_diffrn_reflns_theta_min         4.53
_exptl_absorpt_coefficient_mu    2.055
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.552
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
    Higashi, T. (1999). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             320.00
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 2414 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.011(17)
_refine_ls_extinction_coef       0.0086(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         5343
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0538
_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^)+(0.1157P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1548
_refine_ls_wR_factor_ref         0.1690
_reflns_number_gt                3966
_reflns_number_total             5343
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol052041bsi20050912_081239.cif
_cod_data_source_block           10ab
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '86.5-87.5 \%C' was changed
to '360.1(5)' -- it was converted from degrees Celsius(C) to
Kelvins(K), the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 

 Corrected the value of the '_refine_diff_density_rms' data item
 by removing an ASCII start of heading (SOH) symbol.

 Antanas Vaitkus,
 2019-12-11
;
_cod_original_cell_volume        812.73(16)
_cod_database_code               1556114