#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/33/4023316.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_4023316
loop_
_publ_author_name
'Francesca Cardona'
'Daniela Lalli'
'Cristina Faggi'
'Andrea Goti'
'Alberto Brandi'
_publ_contact_author_address
;
CRIST
Dipartimento di Chimica
Universit%a di Firenze
Via della Lastruccia 3
I-50019 Sesto Fiorentino
Firenze, Italy
;
_publ_contact_author_email       cristina.faggi@unifi.it
_publ_contact_author_name        'Cristina Faggi'
_publ_section_title
;
 Quasienantiomeric Levoglucosenone and Isolevoglucosenone
 Allow the Parallel Kinetic Resolution of a Racemic Nitrone
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1999
_journal_page_last               2002
_journal_paper_doi               10.1021/jo702403b
_journal_volume                  73
_journal_year                    2008
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C14 H21 N O5'
_chemical_formula_sum            'C14 H21 N O5'
_chemical_formula_weight         283.32
_chemical_name_systematic
;
 ?
;
_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
_audit_update_record
;
2007-10-08 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.297(1)
_cell_length_b                   12.593(1)
_cell_length_c                   18.072(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      41.95
_cell_measurement_theta_min      14.82
_cell_volume                     1433.1(3)
_computing_cell_refinement       'Siemens P4'
_computing_data_collection       'Siemens P4'
_computing_data_reduction        'Siemens P4'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Ciftab
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Sir97 (Altomare, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.934
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       'profile data from theta\2theta 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  0.0556
_diffrn_reflns_av_sigmaI/netI    0.0320
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            1838
_diffrn_reflns_theta_full        64.52
_diffrn_reflns_theta_max         64.52
_diffrn_reflns_theta_min         4.28
_diffrn_standards_decay_%        50
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.828
_exptl_absorpt_correction_T_max  0.9054
_exptl_absorpt_correction_T_min  0.8404
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(3)
_refine_ls_extinction_coef       0.0300(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         1670
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0341
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0606P)²+0.1485P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0941
_reflns_number_gt                1610
_reflns_number_total             1670
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702403b-File002.cif
_cod_data_source_block           Compound8
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4023316
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.8915(3) 0.23740(16) 0.33813(10) 0.0579(5) Uani 1 1 d . . .
O1 O 0.8209(4) -0.04552(15) 0.36212(13) 0.0942(7) Uani 1 1 d . . .
O2 O 0.6018(3) 0.10823(13) 0.49021(8) 0.0637(5) Uani 1 1 d . . .
O3 O 0.3556(3) -0.00384(13) 0.44290(9) 0.0645(5) Uani 1 1 d . . .
O4 O 0.7153(3) 0.27201(13) 0.38636(9) 0.0702(5) Uani 1 1 d . . .
O5 O 0.5149(2) 0.19765(14) 0.19473(7) 0.0540(4) Uani 1 1 d . . .
C1 C 0.5764(4) 0.01037(18) 0.45452(13) 0.0596(6) Uani 1 1 d . . .
H1 H 0.629(4) -0.049(2) 0.4849(14) 0.071(8) Uiso 1 1 d . . .
C2 C 0.6874(4) 0.01755(16) 0.38058(13) 0.0554(5) Uani 1 1 d . . .
C3 C 0.6163(3) 0.10962(16) 0.33227(10) 0.0447(5) Uani 1 1 d . . .
H3 H 0.502(4) 0.0835(18) 0.2978(14) 0.060(7) Uiso 1 1 d . . .
C4 C 0.5353(4) 0.20424(16) 0.37723(11) 0.0494(5) Uani 1 1 d . . .
H4 H 0.428(5) 0.245(2) 0.3510(14) 0.067(7) Uiso 1 1 d . . .
C5 C 0.4499(4) 0.17350(18) 0.45259(11) 0.0566(5) Uani 1 1 d . . .
H5 H 0.423(5) 0.235(2) 0.4797(14) 0.072(8) Uiso 1 1 d . . .
C6 C 0.2622(4) 0.1001(2) 0.44692(15) 0.0649(6) Uani 1 1 d . . .
H6A H 0.181(6) 0.103(3) 0.495(2) 0.099(10) Uiso 1 1 d . . .
H6B H 0.187(4) 0.109(2) 0.4050(14) 0.058(7) Uiso 1 1 d . . .
C1' C 0.7957(3) 0.15788(18) 0.28724(11) 0.0483(5) Uani 1 1 d . . .
H1' H 0.896(4) 0.1042(19) 0.2777(13) 0.062(7) Uiso 1 1 d . . .
C2' C 0.7279(3) 0.2175(2) 0.21577(11) 0.0520(5) Uani 1 1 d . . .
H2' H 0.821(4) 0.1966(18) 0.1740(12) 0.054(6) Uiso 1 1 d . . .
C3' C 0.7636(5) 0.3346(2) 0.23397(14) 0.0678(7) Uani 1 1 d . . .
H3'A H 0.810(6) 0.368(3) 0.1914(19) 0.092(10) Uiso 1 1 d . . .
H3'B H 0.628(5) 0.362(2) 0.2604(16) 0.077(8) Uiso 1 1 d . . .
C4' C 0.9388(5) 0.3296(2) 0.29128(15) 0.0697(7) Uani 1 1 d . . .
H4'A H 0.955(5) 0.391(2) 0.3234(16) 0.079(8) Uiso 1 1 d . . .
H4'B H 1.082(7) 0.321(3) 0.268(2) 0.112(12) Uiso 1 1 d . . .
C7 C 0.4813(3) 0.14011(18) 0.12675(10) 0.0499(5) Uani 1 1 d . . .
C8 C 0.5602(5) 0.2042(2) 0.06115(11) 0.0699(7) Uani 1 1 d . . .
H8A H 0.7120 0.2105 0.0636 0.102(4) Uiso 1 1 calc R . .
H8B H 0.4975 0.2737 0.0623 0.102(4) Uiso 1 1 calc R . .
H8C H 0.5211 0.1690 0.0161 0.102(4) Uiso 1 1 calc R . .
C9 C 0.5873(5) 0.0325(2) 0.12959(15) 0.0717(7) Uani 1 1 d . . .
H9A H 0.7387 0.0415 0.1312 0.102(4) Uiso 1 1 calc R . .
H9B H 0.5495 -0.0075 0.0863 0.102(4) Uiso 1 1 calc R . .
H9C H 0.5413 -0.0049 0.1730 0.102(4) Uiso 1 1 calc R . .
C10 C 0.2419(4) 0.1302(3) 0.12348(16) 0.0864(9) Uani 1 1 d . . .
H10A H 0.1928 0.0901 0.1653 0.102(4) Uiso 1 1 calc R . .
H10B H 0.2018 0.0945 0.0787 0.102(4) Uiso 1 1 calc R . .
H10C H 0.1793 0.1997 0.1244 0.102(4) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4' N1 O4 105.04(19) . . ?
C4' N1 C1' 104.98(18) . . ?
O4 N1 C1' 105.02(15) . . ?
C1 O2 C5 102.13(17) . . ?
C1 O3 C6 106.21(19) . . ?
C4 O4 N1 110.59(14) . . ?
C2' O5 C7 117.17(15) . . ?
O2 C1 O3 106.9(2) . . ?
O2 C1 C2 107.57(19) . . ?
O3 C1 C2 109.30(19) . . ?
O2 C1 H1 111.8(15) . . ?
O3 C1 H1 108.7(16) . . ?
C2 C1 H1 112.4(16) . . ?
O1 C2 C1 121.9(2) . . ?
O1 C2 C3 123.4(2) . . ?
C1 C2 C3 114.68(18) . . ?
C2 C3 C1' 113.19(18) . . ?
C2 C3 C4 112.80(17) . . ?
C1' C3 C4 102.75(17) . . ?
C2 C3 H3 108.5(14) . . ?
C1' C3 H3 109.3(14) . . ?
C4 C3 H3 110.2(14) . . ?
O4 C4 C5 109.31(17) . . ?
O4 C4 C3 105.20(17) . . ?
C5 C4 C3 113.39(18) . . ?
O4 C4 H4 106.9(15) . . ?
C5 C4 H4 109.1(16) . . ?
C3 C4 H4 112.6(15) . . ?
O2 C5 C6 101.78(18) . . ?
O2 C5 C4 109.6(2) . . ?
C6 C5 C4 112.02(19) . . ?
O2 C5 H5 110.4(18) . . ?
C6 C5 H5 113.6(18) . . ?
C4 C5 H5 109.2(16) . . ?
O3 C6 C5 104.0(2) . . ?
O3 C6 H6A 106.3(19) . . ?
C5 C6 H6A 109(2) . . ?
O3 C6 H6B 106.7(16) . . ?
C5 C6 H6B 113.2(16) . . ?
H6A C6 H6B 117(2) . . ?
N1 C1' C3 103.87(16) . . ?
N1 C1' C2' 107.44(19) . . ?
C3 C1' C2' 115.73(17) . . ?
N1 C1' H1' 108.9(15) . . ?
C3 C1' H1' 108.1(15) . . ?
C2' C1' H1' 112.3(15) . . ?
O5 C2' C3' 111.6(2) . . ?
O5 C2' C1' 113.44(18) . . ?
C3' C2' C1' 104.32(18) . . ?
O5 C2' H2' 107.8(14) . . ?
C3' C2' H2' 109.5(13) . . ?
C1' C2' H2' 110.1(13) . . ?
C4' C3' C2' 102.4(2) . . ?
C4' C3' H3'A 111(2) . . ?
C2' C3' H3'A 108(2) . . ?
C4' C3' H3'B 107.4(16) . . ?
C2' C3' H3'B 107.6(16) . . ?
H3'A C3' H3'B 120(3) . . ?
N1 C4' C3' 106.2(2) . . ?
N1 C4' H4'A 107.8(17) . . ?
C3' C4' H4'A 116.9(19) . . ?
N1 C4' H4'B 110(2) . . ?
C3' C4' H4'B 112(2) . . ?
H4'A C4' H4'B 104(3) . . ?
O5 C7 C9 110.90(18) . . ?
O5 C7 C10 102.77(18) . . ?
C9 C7 C10 111.6(2) . . ?
O5 C7 C8 110.49(19) . . ?
C9 C7 C8 111.00(18) . . ?
C10 C7 C8 109.8(2) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C4' 1.468(3) . ?
N1 O4 1.476(3) . ?
N1 C1' 1.487(3) . ?
O1 C2 1.204(3) . ?
O2 C1 1.400(3) . ?
O2 C5 1.433(3) . ?
O3 C1 1.418(3) . ?
O3 C6 1.437(3) . ?
O4 C4 1.428(3) . ?
O5 C2' 1.416(3) . ?
O5 C7 1.442(2) . ?
C1 C2 1.511(3) . ?
C1 H1 0.98(3) . ?
C2 C3 1.519(3) . ?
C3 C1' 1.519(3) . ?
C3 C4 1.530(3) . ?
C3 H3 1.01(3) . ?
C4 C5 1.515(3) . ?
C4 H4 0.97(3) . ?
C5 C6 1.504(4) . ?
C5 H5 0.93(3) . ?
C6 H6A 1.01(4) . ?
C6 H6B 0.90(3) . ?
C1' C2' 1.554(3) . ?
C1' H1' 0.94(3) . ?
C2' C3' 1.527(4) . ?
C2' H2' 0.99(2) . ?
C3' C4' 1.514(4) . ?
C3' H3'A 0.92(4) . ?
C3' H3'B 1.04(3) . ?
C4' H4'A 0.97(3) . ?
C4' H4'B 1.00(4) . ?
C7 C9 1.512(3) . ?
C7 C10 1.514(3) . ?
C7 C8 1.518(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658648
