#------------------------------------------------------------------------------
#$Date: 2017-07-12 15:28:44 +0300 (Wed, 12 Jul 2017) $
#$Revision: 198673 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/34/1503489.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1503489
loop_
_publ_author_name
'Burkhard, Johannes A.'
'Guérot, Carine'
'Knust, Henner'
'Carreira, Erick M.'
_publ_section_title
;
 Expanding the azaspiro[3.3]heptane family: synthesis of novel highly
 functionalized building blocks.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              66
_journal_page_last               69
_journal_paper_doi               10.1021/ol2028459
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C12 H15 N O4 S, 0.333(H2 O)'
_chemical_formula_sum            'C12 H15.67 N O4.33 S'
_chemical_formula_weight         275.31
_chemical_name_systematic
; 
 6-tosyl-1-oxa-6-azaspiro[3.3]heptan-3-ol 
;
_space_group_IT_number           148
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_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                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            18
_cell_length_a                   23.477(3)
_cell_length_b                   23.477(3)
_cell_length_c                   12.0406(13)
_cell_measurement_temperature    100(2)
_cell_volume                     5747.3(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Platon, Ortep'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement
'OLEX2 (Dolomanov, 2009), SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0981
_diffrn_reflns_av_sigmaI/netI    0.0475
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12664
_diffrn_reflns_theta_full        24.84
_diffrn_reflns_theta_max         24.84
_diffrn_reflns_theta_min         2.62
_exptl_absorpt_coefficient_mu    0.263
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2610
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.039
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.299
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2200
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.299
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0518
_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/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1623
_refine_ls_wR_factor_ref         0.1772
_reflns_number_gt                1771
_reflns_number_total             2200
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol2028459_si_003.cif
_cod_data_source_block           ca210711_0ma
_cod_depositor_comments
;
 Marking attached hydrogen atoms.

 Antanas Vaitkus,
 2017-07-12
;
_cod_original_sg_symbol_H-M      R-3
_cod_database_code               1503489
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_attached_hydrogens
S29 S -0.40692(4) -0.10054(3) 0.22074(5) 0.0251(3) Uani 1 1 d . 0
O21 O -0.53354(11) -0.23699(10) 0.51990(16) 0.0339(6) Uani 1 1 d . 0
O28 O -0.54859(12) -0.34424(10) 0.33794(18) 0.0414(6) Uani 1 1 d . 0
O30 O -0.43695(11) -0.11374(10) 0.11307(16) 0.0319(5) Uani 1 1 d . 0
O31 O -0.33796(9) -0.07765(10) 0.22912(16) 0.0309(5) Uani 1 1 d . 0
N26 N -0.44395(11) -0.16937(11) 0.28814(19) 0.0229(6) Uani 1 1 d . 0
C22 C -0.55690(18) -0.30731(15) 0.5245(3) 0.0355(8) Uani 1 1 d . 0
H22A H -0.6101(17) -0.3363(16) 0.504(3) 0.043 Uiso 1 1 d . 0
H22B H -0.5481(17) -0.3184(18) 0.586(3) 0.043 Uiso 1 1 d . 0
C23 C -0.51440(16) -0.30298(14) 0.4248(2) 0.0318(7) Uani 1 1 d . 0
H23 H -0.4718 -0.3069 0.4490 0.038 Uiso 1 1 calc R 0
C24 C -0.49858(14) -0.23063(14) 0.4181(2) 0.0257(7) Uani 1 1 d . 0
C25 C -0.51626(13) -0.20582(14) 0.3131(2) 0.0260(7) Uani 1 1 d . 0
H25A H -0.5458 -0.2443 0.2533 0.031 Uiso 1 1 calc R 0
H25B H -0.5370 -0.1742 0.3291 0.031 Uiso 1 1 calc R 0
C27 C -0.42763(14) -0.17486(14) 0.4069(2) 0.0268(7) Uani 1 1 d . 0
H27A H -0.4157 -0.1318 0.4575 0.032 Uiso 1 1 calc R 0
H27B H -0.3910 -0.1901 0.4169 0.032 Uiso 1 1 calc R 0
C32 C -0.42338(14) -0.04363(13) 0.2856(2) 0.0249(7) Uani 1 1 d . 0
C33 C -0.37946(15) -0.00082(14) 0.3651(3) 0.0329(7) Uani 1 1 d . 0
H33 H -0.3355 -0.0025 0.3855 0.039 Uiso 1 1 calc R 0
C34 C -0.39260(15) 0.04350(14) 0.4171(3) 0.0352(8) Uani 1 1 d . 0
H34 H -0.3590 0.0761 0.4794 0.042 Uiso 1 1 calc R 0
C35 C -0.44898(15) 0.04714(14) 0.3904(2) 0.0310(7) Uani 1 1 d . 0
C36 C -0.49193(15) 0.00369(14) 0.3114(2) 0.0282(7) Uani 1 1 d . 0
H36 H -0.5360 0.0051 0.2911 0.034 Uiso 1 1 calc R 0
C37 C -0.47976(14) -0.04121(14) 0.2581(2) 0.0282(7) Uani 1 1 d . 0
H37 H -0.5134 -0.0739 0.1960 0.034 Uiso 1 1 calc R 0
C38 C -0.46204(16) 0.09670(15) 0.4446(3) 0.0358(8) Uani 1 1 d . 0
H38A H -0.4350 0.1435 0.4010 0.054 Uiso 1 1 calc R 0
H38B H -0.4461 0.1031 0.5309 0.054 Uiso 1 1 calc R 0
H38C H -0.5145 0.0797 0.4412 0.054 Uiso 1 1 calc R 0
H28 H -0.515(3) -0.346(2) 0.278(4) 0.104(17) Uiso 1 1 d . 0
O1 O -0.6667 -0.3333 0.292(3) 0.61(3) Uani 1 3 d S 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O31 S29 O30 119.10(13)
O31 S29 N26 106.34(12)
O30 S29 N26 106.08(12)
O31 S29 C32 108.79(13)
O30 S29 C32 107.22(13)
N26 S29 C32 108.98(13)
C24 O21 C22 91.3(2)
C23 O28 H28 110(3)
C25 N26 C27 91.4(2)
C25 N26 S29 124.01(18)
C27 N26 S29 122.01(18)
O21 C22 C23 91.8(2)
O21 C22 H22A 110.9(17)
C23 C22 H22A 111.5(17)
O21 C22 H22B 112(3)
C23 C22 H22B 117(2)
H22A C22 H22B 112(3)
O28 C23 C22 114.6(3)
O28 C23 C24 117.9(3)
C22 C23 C24 84.5(2)
O28 C23 H23 112.3
C22 C23 H23 112.3
C24 C23 H23 112.3
O21 C24 C27 119.0(2)
O21 C24 C25 119.5(2)
C27 C24 C25 89.3(2)
O21 C24 C23 91.7(2)
C27 C24 C23 120.4(2)
C25 C24 C23 119.8(2)
N26 C25 C24 86.4(2)
N26 C25 H25A 114.2
C24 C25 H25A 114.2
N26 C25 H25B 114.2
C24 C25 H25B 114.2
H25A C25 H25B 111.4
N26 C27 C24 86.7(2)
N26 C27 H27A 114.2
C24 C27 H27A 114.2
N26 C27 H27B 114.2
C24 C27 H27B 114.2
H27A C27 H27B 111.4
C37 C32 C33 120.6(3)
C37 C32 S29 120.1(2)
C33 C32 S29 119.3(2)
C34 C33 C32 119.5(3)
C34 C33 H33 120.3
C32 C33 H33 120.3
C33 C34 C35 121.1(3)
C33 C34 H34 119.4
C35 C34 H34 119.4
C36 C35 C34 118.1(3)
C36 C35 C38 120.9(3)
C34 C35 C38 121.0(3)
C37 C36 C35 121.8(3)
C37 C36 H36 119.1
C35 C36 H36 119.1
C36 C37 C32 118.9(3)
C36 C37 H37 120.5
C32 C37 H37 120.5
C35 C38 H38A 109.5
C35 C38 H38B 109.5
H38A C38 H38B 109.5
C35 C38 H38C 109.5
H38A C38 H38C 109.5
H38B C38 H38C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S29 O31 1.432(2)
S29 O30 1.434(2)
S29 N26 1.619(2)
S29 C32 1.749(3)
O21 C24 1.441(3)
O21 C22 1.457(4)
O28 C23 1.378(4)
O28 H28 1.09(5)
N26 C25 1.500(4)
N26 C27 1.502(3)
C22 C23 1.532(4)
C22 H22A 1.11(3)
C22 H22B 0.85(3)
C23 C24 1.549(4)
C23 H23 1.0900
C24 C27 1.525(4)
C24 C25 1.534(4)
C25 H25A 1.0900
C25 H25B 1.0900
C27 H27A 1.0900
C27 H27B 1.0900
C32 C37 1.393(4)
C32 C33 1.397(4)
C33 C34 1.375(4)
C33 H33 1.0800
C34 C35 1.406(4)
C34 H34 1.0800
C35 C36 1.391(4)
C35 C38 1.493(4)
C36 C37 1.381(4)
C36 H36 1.0800
C37 H37 1.0800
C38 H38A 1.0899
C38 H38B 1.0899
C38 H38C 1.0899
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O31 S29 N26 C25 171.7(2)
O30 S29 N26 C25 -60.6(2)
C32 S29 N26 C25 54.6(2)
O31 S29 N26 C27 54.5(2)
O30 S29 N26 C27 -177.8(2)
C32 S29 N26 C27 -62.7(2)
C24 O21 C22 C23 6.5(2)
O21 C22 C23 O28 -124.3(3)
O21 C22 C23 C24 -6.0(2)
C22 O21 C24 C27 -133.0(3)
C22 O21 C24 C25 119.7(3)
C22 O21 C24 C23 -6.4(2)
O28 C23 C24 O21 121.2(3)
C22 C23 C24 O21 6.1(2)
O28 C23 C24 C27 -113.4(3)
C22 C23 C24 C27 131.6(3)
O28 C23 C24 C25 -4.7(4)
C22 C23 C24 C25 -119.7(3)
C27 N26 C25 C24 -18.8(2)
S29 N26 C25 C24 -149.8(2)
O21 C24 C25 N26 141.9(2)
C27 C24 C25 N26 18.5(2)
C23 C24 C25 N26 -106.7(3)
C25 N26 C27 C24 18.9(2)
S29 N26 C27 C24 151.36(19)
O21 C24 C27 N26 -142.3(2)
C25 C24 C27 N26 -18.44(19)
C23 C24 C27 N26 106.3(3)
O31 S29 C32 C37 158.0(2)
O30 S29 C32 C37 27.9(3)
N26 S29 C32 C37 -86.5(3)
O31 S29 C32 C33 -22.1(3)
O30 S29 C32 C33 -152.1(2)
N26 S29 C32 C33 93.5(3)
C37 C32 C33 C34 0.7(5)
S29 C32 C33 C34 -179.3(2)
C32 C33 C34 C35 -0.9(5)
C33 C34 C35 C36 1.2(5)
C33 C34 C35 C38 -178.1(3)
C34 C35 C36 C37 -1.2(4)
C38 C35 C36 C37 178.1(3)
C35 C36 C37 C32 1.0(4)
C33 C32 C37 C36 -0.7(4)
S29 C32 C37 C36 179.3(2)
