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_7110518
_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         '(C33 H32 O4 . C11 H14 N2 O1)'
_chemical_formula_sum            'C44 H46 N2 O5'
_chemical_formula_weight         682.83
_chemical_name_systematic
; 
bis(R,R)-(-)-trans-2,3-bis(diphenylhydroxymethyl)-1,4-dioxaspiro(4.4)nonane
N-nitroso-4-phenylpiperidine  clathrate 
;
_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'
_atom_sites_solution_hydrogens   'geom, hydroxy H atom difmap'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 97.04(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.292(2)
_cell_length_b                   9.536(2)
_cell_length_c                   17.654(4)
_cell_measurement_reflns_used    34
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29
_cell_measurement_theta_min      8
_cell_volume                     1886.7(7)
_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  0.0244
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3511
_diffrn_reflns_theta_max         66.09
_diffrn_reflns_theta_min         2.52
_diffrn_standards_decay_%        1.7
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.620
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_method    'NOT MEASURED'
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.21(32)
_refine_ls_extinction_coef       0.0030(5)
_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   1.072
_refine_ls_goodness_of_fit_obs   1.126
_refine_ls_hydrogen_treatment    'hydroxy H atoms refall; riding model'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     478
_refine_ls_number_reflns         3122
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.146
_refine_ls_restrained_S_obs      1.177
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_obs          0.0418
_refine_ls_shift/esd_max         -0.085
_refine_ls_shift/esd_mean        0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0778P)^2^+0.1176P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1271
_refine_ls_wR_factor_obs         0.1108
_reflns_number_observed          2633
_reflns_number_total             3418
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            901718fsup1.cif
_cod_data_source_block           3-5b
_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 2.4.2 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^)+(0.0778P)^2^+0.1176P] 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^)+(0.0778P)^2^+0.1176P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7110518