N-Nitrosopiperidines with chirality solely due to hindered rotation about the N‒N bond: enantioselective inclusion complexation with optically active hosts
Olszewska, Teresa; Milewska, Maria J.; Połoński, Tadeusz; Gdaniec, Maria; Chemical Communications  (1999) 1385–; doi:10.1039/a901718f

data_7110517
_publ_section_title
;
 N-Nitrosopiperidines with chirality solely due to hindered rotation about
 the N--N bond: enantioselective inclusion complexation with optically
 active hosts
;
_journal_issue                   15
_journal_name_full               'Chemical Communications'
_journal_page_first              1385
_journal_paper_doi               10.1039/a901718f
_journal_year                    1999
_chemical_formula_moiety         '2 (C33 H32 O4).C12 H16 N2 O1'
_chemical_formula_sum            'C78 H80 N2 O9'
_chemical_formula_weight         1189.44
_chemical_melting_point          403.15
_chemical_name_systematic
; 
bis(R,R)-(-)-trans-2,3-bis(diphenylhydroxymethyl)-1,4-dioxaspiro(4.4)nonane
N-nitroso-4-benzylpiperidine 2:1 clathrate
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 117.94(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   35.720(7)
_cell_length_b                   8.605(2)
_cell_length_c                   23.661(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22
_cell_measurement_theta_min      5
_cell_volume                     6425(3)
_computing_cell_refinement       'Kuma KM-4 software (Kuma Diffraction, 1991)'
_computing_data_collection       'Kuma KM-4 sofware (Kuma Diffraction, 1991)'
_computing_data_reduction        'Kuma KM-4 software (Kuma Diffraction, 1991)'
_computing_molecular_graphics
'Stereochemical Workstation (Siemens Analytical X-Ray Instruments, Inc., 1989)'
_computing_publication_material  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'KM-4 four-circle diffractometer'
_diffrn_measurement_method       '\w/2\q scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            4792
_diffrn_reflns_theta_max         60.04
_diffrn_reflns_theta_min         2.11
_diffrn_standards_decay_%        1.5
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.632
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             2536
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(25)
_refine_ls_extinction_coef       0.00075(6)
_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_all   1.069
_refine_ls_goodness_of_fit_obs   1.099
_refine_ls_hydrogen_treatment    'riding model'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     812
_refine_ls_number_reflns         4391
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.126
_refine_ls_restrained_S_obs      1.134
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_obs          0.0404
_refine_ls_shift/esd_max         -0.013
_refine_ls_shift/esd_mean        0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0762P)^2^+0.8612P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1139
_refine_ls_wR_factor_obs         0.1020
_reflns_number_observed          3928
_reflns_number_total             4710
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            901718fsup1.cif
_cod_data_source_block           4-2(5b)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '130C' was changed to '403.15' - it
was converted from degrees Celsius(C) to
Kelvins(K).

'_symmetry_cell_setting' value 'MONOCLINIC' changed to
'monoclinic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'NONE' changed to
'none' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0762P)^2^+0.8612P] where P=(Fo^2^+2Fc^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^(Fo^2^)+(0.0762P)^2^+0.8612P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        6425.0(24)
_cod_original_sg_symbol_H-M      C2
_cod_database_code               7110517