# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_FII
_database_code_depnum_ccdc_archive 'CCDC 1556517'
_audit_update_record             
;
2017-06-16 deposited with the CCDC.
2017-12-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
1-(2,2,3-trimethyl-1,3-oxazolidin-5-yl)butane-1,2,3,4-tetrol
;
_chemical_name_common            ?
_chemical_melting_point          395.3
_chemical_formula_moiety         'C10 H21 N O5'
_chemical_formula_sum            'C10 H21 N O5'
_chemical_formula_weight         235.28

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.0282(6)
_cell_length_b                   9.9007(8)
_cell_length_c                   17.2379(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1199.48(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    101(2)
_cell_measurement_reflns_used    9958
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      27.09

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_preparation       
'crystallised from acetone solution at room temperature'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
Polymorph: metastable form II
;

_diffrn_ambient_temperature      101(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23084
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.130
_diffrn_reflns_theta_max         27.122
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2631
_reflns_number_gt                2471
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.713
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0398P)²+0.2159P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.020(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1002 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(2)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2631
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0275
_refine_ls_wR_factor_ref         0.0698
_refine_ls_wR_factor_gt          0.0675
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8589(2) 0.58394(18) 0.62757(9) 0.0198(4) Uani 1 1 d . . . . .
H1A H 0.9320 0.6685 0.6348 0.024 Uiso 1 1 calc R U . . .
H1B H 0.7868 0.5666 0.6759 0.024 Uiso 1 1 calc R U . . .
C2 C 0.7204(2) 0.60237(16) 0.56117(9) 0.0154(3) Uani 1 1 d . . . . .
C3 C 0.5875(2) 0.48178(16) 0.54553(9) 0.0131(3) Uani 1 1 d . . . . .
C4 C 0.4105(2) 0.53404(16) 0.50259(9) 0.0133(3) Uani 1 1 d . . . . .
C5 C 0.2915(2) 0.42025(16) 0.46850(9) 0.0137(3) Uani 1 1 d . . . . .
H5 H 0.2546 0.3558 0.5106 0.016 Uiso 1 1 calc R U . . .
C6 C 0.3922(2) 0.34364(17) 0.40347(10) 0.0166(3) Uani 1 1 d . . . . .
H6A H 0.4922 0.3998 0.3790 0.020 Uiso 1 1 calc R U . . .
H6B H 0.4500 0.2589 0.4229 0.020 Uiso 1 1 calc R U . . .
C7 C 0.1156(2) 0.43821(16) 0.35160(9) 0.0164(3) Uani 1 1 d . . . . .
C8 C 0.3057(3) 0.27790(19) 0.27158(10) 0.0236(4) Uani 1 1 d . . . . .
H8A H 0.3877 0.3498 0.2513 0.035 Uiso 1 1 calc R U . . .
H8B H 0.1973 0.2649 0.2366 0.035 Uiso 1 1 calc R U . . .
H8C H 0.3785 0.1937 0.2752 0.035 Uiso 1 1 calc R U . . .
C9 C -0.0894(2) 0.40441(19) 0.33181(10) 0.0231(4) Uani 1 1 d . . . . .
H9A H -0.1361 0.3346 0.3673 0.035 Uiso 1 1 calc R U . . .
H9B H -0.0964 0.3711 0.2783 0.035 Uiso 1 1 calc R U . . .
H9C H -0.1679 0.4857 0.3370 0.035 Uiso 1 1 calc R U . . .
C10 C 0.1881(3) 0.55684(18) 0.30303(11) 0.0252(4) Uani 1 1 d . . . . .
H10A H 0.1188 0.6390 0.3174 0.038 Uiso 1 1 calc R U . . .
H10B H 0.1678 0.5376 0.2479 0.038 Uiso 1 1 calc R U . . .
H10C H 0.3243 0.5699 0.3127 0.038 Uiso 1 1 calc R U . . .
H1 H 1.087(3) 0.511(2) 0.5996(12) 0.026(6) Uiso 1 1 d . . . . .
H2 H 0.905(4) 0.589(3) 0.4841(14) 0.035(7) Uiso 1 1 d . . . . .
H3 H 0.597(3) 0.356(2) 0.6224(13) 0.028(6) Uiso 1 1 d . . . . .
H4 H 0.297(4) 0.693(3) 0.5426(13) 0.038(6) Uiso 1 1 d . . . . .
H2A H 0.642(3) 0.681(2) 0.5748(10) 0.012(4) Uiso 1 1 d . . . . .
H3A H 0.659(3) 0.419(2) 0.5127(10) 0.012(4) Uiso 1 1 d . . . . .
H4A H 0.453(2) 0.5917(19) 0.4594(10) 0.008(4) Uiso 1 1 d . . . . .
N1 N 0.23619(19) 0.31576(14) 0.34893(8) 0.0152(3) Uani 1 1 d . . . . .
O1 O 0.98775(17) 0.47566(13) 0.61471(7) 0.0184(3) Uani 1 1 d . . . . .
O2 O 0.81795(18) 0.63502(12) 0.49037(7) 0.0173(3) Uani 1 1 d . . . . .
O3 O 0.52538(17) 0.41781(13) 0.61464(7) 0.0187(3) Uani 1 1 d . . . . .
O4 O 0.29645(16) 0.60855(12) 0.55612(7) 0.0155(3) Uani 1 1 d . . . . .
O5 O 0.12200(16) 0.47479(13) 0.43249(6) 0.0176(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C1 O1 1.421(2) . ?
C1 C2 1.514(2) . ?
C2 O2 1.4368(19) . ?
C2 C3 1.540(2) . ?
C3 O3 1.4181(19) . ?
C3 C4 1.537(2) . ?
C4 O4 1.4278(19) . ?
C4 C5 1.521(2) . ?
C5 O5 1.4478(18) . ?
C5 C6 1.528(2) . ?
C6 N1 1.471(2) . ?
C7 O5 1.441(2) . ?
C7 N1 1.480(2) . ?
C7 C9 1.518(2) . ?
C7 C10 1.530(2) . ?
C8 N1 1.469(2) . ?

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
O1 C1 C2 112.52(13) . . ?
O2 C2 C1 111.25(13) . . ?
O2 C2 C3 108.37(12) . . ?
C1 C2 C3 115.41(14) . . ?
O3 C3 C4 107.80(12) . . ?
O3 C3 C2 112.70(13) . . ?
C4 C3 C2 108.31(13) . . ?
O4 C4 C5 108.86(12) . . ?
O4 C4 C3 108.49(13) . . ?
C5 C4 C3 112.44(13) . . ?
O5 C5 C4 110.00(12) . . ?
O5 C5 C6 104.59(12) . . ?
C4 C5 C6 113.34(13) . . ?
N1 C6 C5 102.52(12) . . ?
O5 C7 N1 102.60(12) . . ?
O5 C7 C9 107.61(13) . . ?
N1 C7 C9 110.85(13) . . ?
O5 C7 C10 109.04(13) . . ?
N1 C7 C10 114.90(14) . . ?
C9 C7 C10 111.25(15) . . ?
C8 N1 C6 112.34(13) . . ?
C8 N1 C7 115.34(14) . . ?
C6 N1 C7 104.67(12) . . ?
C7 O5 C5 110.29(11) . . ?

_refine_diff_density_max         0.244
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.035

_shelxl_version_number           2014-3

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_FI
_database_code_depnum_ccdc_archive 'CCDC 1579804'
_audit_update_record             
;
2017-10-13 deposited with the CCDC.
2017-12-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
1-(2,2,3-trimethyl-1,3-oxazolidin-5-yl)butane-1,2,3,4-tetrol
;
_chemical_name_common            ?
_chemical_melting_point          410.4
_chemical_formula_moiety         'C10 H21 N O5'
_chemical_formula_sum            'C10 H21 N O5'
_chemical_formula_weight         235.28

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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'

_cell_length_a                   6.0781(3)
_cell_length_b                   10.8821(6)
_cell_length_c                   17.8535(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1180.87(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9952
_cell_measurement_theta_min      3.35
_cell_measurement_theta_max      26.985

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_preparation       
'crystallised from acetone solution at room temperature'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.105
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
Polymorph: form I
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\ f and \ w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20697
_diffrn_reflns_av_unetI/netI     0.0070
_diffrn_reflns_av_R_equivalents  0.0137
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.541
_diffrn_reflns_theta_max         26.985
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             2532
_reflns_number_gt                2509
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.711
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    0.992

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0326P)²+0.2497P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.084(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1038 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(7)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2532
_refine_ls_number_parameters     197
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0229
_refine_ls_R_factor_gt           0.0228
_refine_ls_wR_factor_ref         0.0596
_refine_ls_wR_factor_gt          0.0595
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5269(2) 0.22933(12) 0.17757(7) 0.0123(3) Uani 1 1 d . . . . .
C2 C 0.6489(2) 0.34252(11) 0.20562(7) 0.0098(3) Uani 1 1 d . . . . .
C3 C 0.8167(2) 0.30856(11) 0.26654(7) 0.0092(2) Uani 1 1 d . . . . .
C4 C 0.9339(2) 0.42083(11) 0.29926(7) 0.0093(2) Uani 1 1 d . . . . .
C5 C 1.0812(2) 0.38370(11) 0.36446(7) 0.0103(3) Uani 1 1 d . . . . .
C6 C 0.9525(2) 0.33152(12) 0.43089(7) 0.0135(3) Uani 1 1 d . . . . .
C7 C 1.1397(2) 0.50467(12) 0.47173(7) 0.0131(3) Uani 1 1 d . . . . .
C8 C 0.9622(2) 0.36839(14) 0.56571(7) 0.0186(3) Uani 1 1 d . . . . .
H8A H 0.8183 0.4087 0.5626 0.028 Uiso 1 1 calc R U . . .
H8B H 1.0502 0.4075 0.6050 0.028 Uiso 1 1 calc R U . . .
H8C H 0.9419 0.2812 0.5777 0.028 Uiso 1 1 calc R U . . .
C9 C 1.3466(3) 0.54406(14) 0.51278(8) 0.0204(3) Uani 1 1 d . . . . .
H9A H 1.4613 0.4818 0.5058 0.031 Uiso 1 1 calc R U . . .
H9B H 1.3144 0.5528 0.5663 0.031 Uiso 1 1 calc R U . . .
H9C H 1.3976 0.6229 0.4928 0.031 Uiso 1 1 calc R U . . .
C10 C 0.9585(3) 0.60172(13) 0.47721(8) 0.0216(3) Uani 1 1 d . . . . .
H10A H 1.0080 0.6777 0.4530 0.032 Uiso 1 1 calc R U . . .
H10B H 0.9258 0.6181 0.5300 0.032 Uiso 1 1 calc R U . . .
H10C H 0.8256 0.5716 0.4521 0.032 Uiso 1 1 calc R U . . .
N1 N 1.07534(19) 0.37987(10) 0.49416(6) 0.0127(2) Uani 1 1 d . . . . .
O1 O 0.41501(16) 0.16687(8) 0.23687(6) 0.0140(2) Uani 1 1 d . . . . .
O2 O 0.48640(15) 0.42500(9) 0.23428(6) 0.0138(2) Uani 1 1 d . . . . .
O3 O 0.98007(15) 0.22977(9) 0.23460(5) 0.0131(2) Uani 1 1 d . . . . .
O4 O 1.05371(15) 0.48491(8) 0.24231(5) 0.0106(2) Uani 1 1 d . . . . .
O5 O 1.19504(15) 0.48939(9) 0.39402(5) 0.0136(2) Uani 1 1 d . . . . .
H1 H 0.287(4) 0.1959(19) 0.2424(12) 0.025(5) Uiso 1 1 d . . . . .
H2A H 0.537(3) 0.495(2) 0.2411(10) 0.024(5) Uiso 1 1 d . . . . .
H3A H 0.949(4) 0.158(2) 0.2401(12) 0.033(6) Uiso 1 1 d . . . . .
H4A H 1.170(4) 0.451(2) 0.2352(12) 0.029(5) Uiso 1 1 d . . . . .
H5 H 1.192(3) 0.3282(15) 0.3468(9) 0.011(4) Uiso 1 1 d . . . . .
H4 H 0.821(3) 0.4755(15) 0.3179(8) 0.008(4) Uiso 1 1 d . . . . .
H3 H 0.737(3) 0.2654(16) 0.3061(9) 0.010(4) Uiso 1 1 d . . . . .
H2 H 0.725(3) 0.3815(15) 0.1632(8) 0.003(3) Uiso 1 1 d . . . . .
H1A H 0.421(3) 0.2557(16) 0.1394(10) 0.015(4) Uiso 1 1 d . . . . .
H1B H 0.624(3) 0.1712(16) 0.1561(9) 0.013(4) Uiso 1 1 d . . . . .
H6A H 0.798(3) 0.3587(15) 0.4282(9) 0.009(4) Uiso 1 1 d . . . . .
H6B H 0.951(3) 0.2426(17) 0.4315(10) 0.017(4) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C1 O1 1.4303(16) . ?
C1 C2 1.5223(16) . ?
C2 O2 1.4293(15) . ?
C2 C3 1.5360(17) . ?
C3 O3 1.4307(15) . ?
C3 C4 1.5303(16) . ?
C4 O4 1.4318(15) . ?
C4 C5 1.5231(17) . ?
C5 O5 1.4422(15) . ?
C5 C6 1.5302(17) . ?
C6 N1 1.4528(17) . ?
C7 O5 1.4372(15) . ?
C7 N1 1.4689(16) . ?
C7 C9 1.5174(19) . ?
C7 C10 1.529(2) . ?
C8 N1 1.4561(16) . ?

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
O1 C1 C2 111.88(10) . . ?
O2 C2 C1 106.82(10) . . ?
O2 C2 C3 110.87(10) . . ?
C1 C2 C3 111.20(10) . . ?
O3 C3 C4 107.89(10) . . ?
O3 C3 C2 108.83(10) . . ?
C4 C3 C2 112.79(10) . . ?
O4 C4 C5 111.91(10) . . ?
O4 C4 C3 110.77(10) . . ?
C5 C4 C3 110.71(9) . . ?
O5 C5 C4 110.49(10) . . ?
O5 C5 C6 104.93(10) . . ?
C4 C5 C6 112.97(10) . . ?
N1 C6 C5 101.86(10) . . ?
O5 C7 N1 102.63(10) . . ?
O5 C7 C9 107.75(11) . . ?
N1 C7 C9 110.49(11) . . ?
O5 C7 C10 108.08(11) . . ?
N1 C7 C10 115.43(11) . . ?
C9 C7 C10 111.77(12) . . ?
C6 N1 C8 114.10(11) . . ?
C6 N1 C7 105.05(10) . . ?
C8 N1 C7 116.38(10) . . ?
C7 O5 C5 109.46(9) . . ?

_refine_diff_density_max         0.243
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.030

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_FI_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1556518'
_audit_update_record             
;
2017-06-16 deposited with the CCDC.
2017-12-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
1-(2,2,3-trimethyl-1,3-oxazolidin-5-yl)butane-1,2,3,4-tetrol
;
_chemical_name_common            ?
_chemical_melting_point          410.4
_chemical_formula_moiety         'C10 H21 N O5'
_chemical_formula_sum            'C10 H21 N O5'
_chemical_formula_weight         235.28

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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'

_cell_length_a                   6.1053(4)
_cell_length_b                   10.9507(7)
_cell_length_c                   18.1001(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1210.12(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    9950
_cell_measurement_theta_min      2.92
_cell_measurement_theta_max      26.20

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_preparation       
'crystallised from acetone solution at room temperature'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
Polymorph: form I
;

_diffrn_ambient_temperature      299(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\ f and \ w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29288
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.250
_diffrn_reflns_theta_max         26.399
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2490
_reflns_number_gt                2286
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.700
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0636P)²+0.0738P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.080(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 892 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2490
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.1008
_refine_ls_wR_factor_gt          0.0887
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_restrained_S_all      1.165
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O 1.0534(3) 0.48153(13) 0.24492(8) 0.0253(3) Uani 1 1 d . . . . .
O1 O 0.4203(3) 0.16316(14) 0.23975(11) 0.0347(4) Uani 1 1 d . . . . .
O2 O 0.4889(2) 0.41888(15) 0.23517(10) 0.0340(4) Uani 1 1 d . . . . .
O3 O 0.9833(2) 0.22850(14) 0.24001(10) 0.0340(4) Uani 1 1 d . . . . .
O5 O 1.1822(3) 0.49282(14) 0.39529(8) 0.0366(4) Uani 1 1 d . . . . .
C1 C 0.5326(4) 0.2244(2) 0.18182(12) 0.0304(5) Uani 1 1 d . . . . .
H1A H 0.4281 0.2477 0.1440 0.037 Uiso 1 1 calc R U . . .
H1B H 0.6374 0.1688 0.1596 0.037 Uiso 1 1 calc R U . . .
C5 C 1.0747(4) 0.38625(18) 0.36670(11) 0.0252(5) Uani 1 1 d . . . . .
C4 C 0.9323(3) 0.41933(17) 0.30099(11) 0.0220(4) Uani 1 1 d . . . . .
H4A H 0.8183 0.4752 0.3186 0.026 Uiso 1 1 calc R U . . .
C6 C 0.9462(4) 0.3358(2) 0.43205(12) 0.0336(5) Uani 1 1 d . . . . .
H6A H 0.7963 0.3652 0.4320 0.040 Uiso 1 1 calc R U . . .
H6B H 0.9458 0.2472 0.4321 0.040 Uiso 1 1 calc R U . . .
C2 C 0.6520(3) 0.33730(18) 0.20859(11) 0.0241(5) Uani 1 1 d . . . . .
H2A H 0.7286 0.3752 0.1669 0.029 Uiso 1 1 calc R U . . .
C3 C 0.8181(3) 0.30700(17) 0.26952(11) 0.0215(4) Uani 1 1 d . . . . .
H3A H 0.7423 0.2643 0.3097 0.026 Uiso 1 1 calc R U . . .
C7 C 1.1339(4) 0.5070(2) 0.47212(12) 0.0325(5) Uani 1 1 d . . . . .
C8 C 0.9570(5) 0.3719(3) 0.56476(14) 0.0495(7) Uani 1 1 d . . . . .
H8A H 0.8155 0.4099 0.5620 0.074 Uiso 1 1 calc R U . . .
H8B H 1.0425 0.4111 0.6024 0.074 Uiso 1 1 calc R U . . .
H8C H 0.9399 0.2870 0.5766 0.074 Uiso 1 1 calc R U . . .
C9 C 1.3430(6) 0.5432(3) 0.51090(16) 0.0560(8) Uani 1 1 d . . . . .
H9A H 1.4541 0.4832 0.5013 0.084 Uiso 1 1 calc R U . . .
H9B H 1.3171 0.5481 0.5631 0.084 Uiso 1 1 calc R U . . .
H9C H 1.3907 0.6213 0.4929 0.084 Uiso 1 1 calc R U . . .
C10 C 0.9581(6) 0.6045(3) 0.4789(2) 0.0623(9) Uani 1 1 d . . . . .
H10A H 1.0074 0.6781 0.4554 0.094 Uiso 1 1 calc R U . . .
H10B H 0.9295 0.6203 0.5302 0.094 Uiso 1 1 calc R U . . .
H10C H 0.8263 0.5766 0.4554 0.094 Uiso 1 1 calc R U . . .
N1 N 1.0676(3) 0.38371(17) 0.49397(10) 0.0317(5) Uani 1 1 d . . . . .
H1 H 0.301(6) 0.191(3) 0.2474(18) 0.053(9) Uiso 1 1 d . . . . .
H2 H 0.538(5) 0.482(3) 0.2412(15) 0.038(8) Uiso 1 1 d . . . . .
H3 H 0.947(6) 0.159(3) 0.2421(17) 0.053(9) Uiso 1 1 d . . . . .
H4 H 1.167(6) 0.446(3) 0.2385(17) 0.047(8) Uiso 1 1 d . . . . .
H5 H 1.188(4) 0.331(2) 0.3520(12) 0.023(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O4 C4 1.429(2) . ?
O1 C1 1.421(3) . ?
O2 C2 1.422(3) . ?
O3 C3 1.429(2) . ?
O5 C7 1.430(3) . ?
O5 C5 1.436(2) . ?
C1 C2 1.515(3) . ?
C5 C4 1.517(3) . ?
C5 C6 1.523(3) . ?
C4 C3 1.524(3) . ?
C6 N1 1.443(3) . ?
C2 C3 1.535(3) . ?
C7 N1 1.464(3) . ?
C7 C9 1.510(4) . ?
C7 C10 1.519(4) . ?
C8 N1 1.454(3) . ?

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
C7 O5 C5 110.15(16) . . ?
O1 C1 C2 112.40(18) . . ?
O5 C5 C4 110.53(16) . . ?
O5 C5 C6 104.52(16) . . ?
C4 C5 C6 113.60(18) . . ?
O4 C4 C5 111.96(16) . . ?
O4 C4 C3 110.86(16) . . ?
C5 C4 C3 111.24(15) . . ?
N1 C6 C5 101.92(17) . . ?
O2 C2 C1 106.52(16) . . ?
O2 C2 C3 110.83(17) . . ?
C1 C2 C3 111.80(17) . . ?
O3 C3 C4 107.62(15) . . ?
O3 C3 C2 109.15(17) . . ?
C4 C3 C2 113.34(16) . . ?
O5 C7 N1 102.69(16) . . ?
O5 C7 C9 107.8(2) . . ?
N1 C7 C9 110.5(2) . . ?
O5 C7 C10 107.5(2) . . ?
N1 C7 C10 115.5(2) . . ?
C9 C7 C10 112.1(2) . . ?
C6 N1 C8 114.4(2) . . ?
C6 N1 C7 105.54(16) . . ?
C8 N1 C7 116.65(19) . . ?

_refine_diff_density_max         0.382
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.095

_shelxl_version_number           2014-3

