#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/63/1506313.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_1506313
loop_
_publ_author_name
'Pansare, Sunil V.'
'Adsool, Vikrant A.'
_publ_contact_author             'Dr. Sunil V. Pansare'
_publ_section_title
;
 Enantioselective synthesis of functionalized medium-sized oxacycles.
;
_journal_issue                   25
_journal_name_full               'Organic letters'
_journal_page_first              5897
_journal_page_last               5899
_journal_paper_doi               10.1021/ol062484v
_journal_volume                  8
_journal_year                    2006
_chemical_formula_sum            'C14 H17 N O3'
_chemical_formula_weight         247.29
_chemical_name_systematic
(3S,5R,6S)-2,6,7-Trimethyl-5-phenyl-1,4-dioxa-7-azaspiro[2.5]octan-8-one
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6454(12)
_cell_length_b                   10.7876(17)
_cell_length_c                   13.704(2)
_cell_measurement_reflns_used    6079
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      30.7
_cell_measurement_theta_min      2.4
_cell_volume                     1278.1(3)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalStructure 3.7.0 (Rigaku)'
_computing_molecular_graphics    'CrystalStructure 3.7.0 (Rigaku)'
_computing_publication_material  'CrystalStructure 3.7.0 (Rigaku)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Giacovazzo et. al., 1994)'
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean 14.63
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0268
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11571
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.79
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_T_max  0.9791
_exptl_absorpt_correction_T_min  0.9688
_exptl_absorpt_correction_type   numerical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.171
_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   -0.1(13)
_refine_ls_extinction_coef       0.013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2916
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0446
_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)+(0.0521P)²+0.2055P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1103
_reflns_number_gt                2685
_reflns_number_total             2916
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol062484vsi20061103_015018.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Numerical' changed to
'numerical' 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_formula_sum        'C14 H17 N O3 '
_cod_database_code               1506313
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
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
O1 O -0.04806(16) 0.29510(13) 0.49274(9) 0.0442(4) Uani 1 1 d .
O2 O 0.07376(18) 0.11116(12) 0.36193(11) 0.0496(4) Uani 1 1 d .
O3 O 0.05358(14) 0.44230(11) 0.38061(9) 0.0344(3) Uani 1 1 d .
N1 N 0.2450(2) 0.25828(13) 0.31235(11) 0.0382(4) Uani 1 1 d .
C1 C -0.2701(2) 0.4001(2) 0.40667(15) 0.0446(5) Uani 1 1 d .
H1 H -0.3643 0.3744 0.4409 0.054 Uiso 1 1 calc R
H2 H -0.2950 0.4194 0.3386 0.054 Uiso 1 1 calc R
H3 H -0.2269 0.4738 0.4384 0.054 Uiso 1 1 calc R
C2 C -0.1546(2) 0.29754(19) 0.40991(14) 0.0414(4) Uani 1 1 d .
H4 H -0.1923 0.2149 0.3869 0.050 Uiso 1 1 calc R
C3 C 0.0102(2) 0.32095(17) 0.39673(13) 0.0359(4) Uani 1 1 d .
C4 C 0.1139(2) 0.22086(17) 0.35573(13) 0.0386(4) Uani 1 1 d .
C5 C 0.3466(3) 0.1652(2) 0.26909(18) 0.0561(6) Uani 1 1 d .
H5 H 0.4214 0.1369 0.3180 0.067 Uiso 1 1 calc R
H6 H 0.4018 0.2015 0.2136 0.067 Uiso 1 1 calc R
H7 H 0.2847 0.0946 0.2467 0.067 Uiso 1 1 calc R
C6 C 0.2967(2) 0.38778(16) 0.30894(13) 0.0350(4) Uani 1 1 d .
H8 H 0.4106 0.3886 0.3216 0.042 Uiso 1 1 calc R
C7 C 0.2701(2) 0.44345(18) 0.20792(13) 0.0411(4) Uani 1 1 d .
H9 H 0.2965 0.3821 0.1579 0.049 Uiso 1 1 calc R
H10 H 0.3355 0.5169 0.1999 0.049 Uiso 1 1 calc R
H11 H 0.1612 0.4671 0.2011 0.049 Uiso 1 1 calc R
C8 C 0.21860(19) 0.45775(16) 0.39176(13) 0.0320(4) Uani 1 1 d .
H12 H 0.2509 0.4198 0.4551 0.038 Uiso 1 1 calc R
C9 C 0.2533(2) 0.59407(16) 0.39483(12) 0.0332(4) Uani 1 1 d .
C10 C 0.3767(2) 0.63576(19) 0.45148(14) 0.0418(5) Uani 1 1 d .
H13 H 0.4380 0.5784 0.4871 0.050 Uiso 1 1 calc R
C11 C 0.4095(3) 0.7618(2) 0.45561(15) 0.0510(6) Uani 1 1 d .
H14 H 0.4942 0.7902 0.4937 0.061 Uiso 1 1 calc R
C12 C 0.3203(3) 0.84583(18) 0.40505(15) 0.0494(5) Uani 1 1 d .
H15 H 0.3434 0.9318 0.4088 0.059 Uiso 1 1 calc R
C13 C 0.1979(3) 0.80583(17) 0.34906(15) 0.0439(5) Uani 1 1 d .
H16 H 0.1362 0.8640 0.3146 0.053 Uiso 1 1 calc R
C14 C 0.1649(2) 0.67922(17) 0.34322(14) 0.0389(4) Uani 1 1 d .
H17 H 0.0815 0.6513 0.3038 0.047 Uiso 1 1 calc R
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C3 O1 C2 60.43(11)
C3 O3 C8 111.15(13)
C4 N1 C5 118.74(17)
C4 N1 C6 123.88(15)
C5 N1 C6 117.34(17)
C3 C2 O1 58.91(12)
C3 C2 C1 121.50(17)
O1 C2 C1 117.29(17)
O3 C3 O1 115.23(15)
O3 C3 C2 116.71(16)
O1 C3 C2 60.66(12)
O3 C3 C4 117.22(15)
O1 C3 C4 114.20(15)
C2 C3 C4 120.10(16)
O2 C4 N1 123.73(18)
O2 C4 C3 119.48(18)
N1 C4 C3 116.77(16)
N1 C6 C8 108.28(14)
N1 C6 C7 110.96(15)
C8 C6 C7 114.50(15)
O3 C8 C9 108.27(14)
O3 C8 C6 107.58(14)
C9 C8 C6 114.72(15)
C14 C9 C10 119.45(17)
C14 C9 C8 121.56(16)
C10 C9 C8 118.99(16)
C11 C10 C9 119.64(19)
C12 C11 C10 120.6(2)
C13 C12 C11 120.31(18)
C12 C13 C14 119.70(19)
C9 C14 C13 120.30(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C3 1.436(2)
O1 C2 1.462(2)
O2 C4 1.236(2)
O3 C3 1.379(2)
O3 C8 1.445(2)
N1 C4 1.342(3)
N1 C5 1.460(3)
N1 C6 1.467(2)
C1 C2 1.491(3)
C2 C3 1.459(3)
C3 C4 1.511(3)
C6 C8 1.521(2)
C6 C7 1.526(3)
C8 C9 1.501(2)
C9 C14 1.389(3)
C9 C10 1.394(3)
C10 C11 1.390(3)
C11 C12 1.377(3)
C12 C13 1.376(3)
C13 C14 1.398(3)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 21199645 ChemSpider
