# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_1303
_database_code_depnum_ccdc_archive 'CCDC 1545186'
_audit_update_record             
;
2017-04-20 deposited with the CCDC.
2017-10-11 downloaded from the CCDC.
;

#------------------ AUDIT DETAILS -------------------------------------------#

_audit_creation_date             
;
'Thu Dec 04 18:41:08 2014'
;
_audit_creation_method           SHELXL-2014/6

_chemical_name_systematic        
;
benzyl 6-deoxy-2,3-O-(1-methylethylidene)-?-D-mannofuranoside 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H22 O5'
_chemical_formula_sum            'C16 H22 O5'
_chemical_formula_weight         294.33

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'
O O 0.0492 0.0322 '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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.7984(1)
_cell_length_b                   7.8542(2)
_cell_length_c                   33.8291(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1540.64(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2724
_cell_measurement_theta_min      5.230
_cell_measurement_theta_max      72.397

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.772
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.70165
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_probe          x-ray
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Onyx
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.1241
_diffrn_reflns_number            4627
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         5.230
_diffrn_reflns_theta_max         72.394
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.896
_diffrn_reflns_point_group_measured_fraction_full 0.960
_reflns_number_total             2724
_reflns_number_gt                2440
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.567
_reflns_Friedel_fraction_max     0.800
_reflns_Friedel_fraction_full    0.861

_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -76.00  -15.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -46.2824   77.0000  -90.0000 61

#__ type_ start__ end____ width___ exp.time_
  2 omega   17.00   75.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       46.2824   77.0000  -60.0000 58

#__ type_ start__ end____ width___ exp.time_
  3 omega  -93.00  -45.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   77.0000   60.0000 48

#__ type_ start__ end____ width___ exp.time_
  4 omega   74.00  125.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   77.0000   30.0000 51

#__ type_ start__ end____ width___ exp.time_
  5 omega   83.00  109.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   77.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega  122.00  148.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   77.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega  130.00  171.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   77.0000   30.0000 41

#__ type_ start__ end____ width___ exp.time_
  8 omega   74.00  168.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   77.0000  150.0000 94

;

_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SIR2004 J.Appl.Cryst.38,381-388'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_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)+(0.0530P)²+0.7945P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 820 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(1)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         2724
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1323
_refine_ls_wR_factor_gt          0.1229
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_restrained_S_all      1.149
_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
O1 O 0.8002(5) -0.1541(3) 0.31987(7) 0.0271(6) Uani 1 1 d . . . . .
O2 O 0.8703(5) 0.1128(3) 0.29832(7) 0.0214(6) Uani 1 1 d . . . . .
O3 O 0.5092(4) 0.1331(3) 0.35979(7) 0.0211(5) Uani 1 1 d . . . . .
O4 O 0.8656(5) 0.4938(4) 0.33309(8) 0.0291(6) Uani 1 1 d . . . . .
O5 O 0.6198(4) -0.0274(3) 0.41503(6) 0.0218(6) Uani 1 1 d . . . . .
C1 C 0.8960(6) 0.1252(5) 0.34039(10) 0.0193(7) Uani 1 1 d . . . . .
H1 H 1.0524 0.1570 0.3485 0.023 Uiso 1 1 calc R U . . .
C2 C 0.8236(7) -0.0545(4) 0.35492(10) 0.0216(8) Uani 1 1 d . . . . .
H2 H 0.9348 -0.1034 0.3736 0.026 Uiso 1 1 calc R U . . .
C3 C 0.5875(7) -0.0265(5) 0.37352(9) 0.0210(8) Uani 1 1 d . . . . .
H3 H 0.4807 -0.1170 0.3656 0.025 Uiso 1 1 calc R U . . .
C4 C 0.7112(6) 0.2409(5) 0.35755(10) 0.0193(7) Uani 1 1 d . . . . .
H4 H 0.7563 0.2750 0.3843 0.023 Uiso 1 1 calc R U . . .
C5 C 0.6560(7) 0.3985(5) 0.33354(10) 0.0205(8) Uani 1 1 d . . . . .
H5 H 0.6164 0.3650 0.3065 0.025 Uiso 1 1 calc R U . . .
C6 C 0.4595(7) 0.4994(5) 0.35101(11) 0.0252(8) Uani 1 1 d . . . . .
H6A H 0.3218 0.4314 0.3508 0.038 Uiso 1 1 calc R U . . .
H6B H 0.4965 0.5304 0.3777 0.038 Uiso 1 1 calc R U . . .
H6C H 0.4350 0.6005 0.3356 0.038 Uiso 1 1 calc R U . . .
C7 C 0.9034(7) -0.0596(5) 0.28768(10) 0.0207(8) Uani 1 1 d . . . . .
C8 C 0.7687(7) -0.0981(6) 0.25068(10) 0.0286(9) Uani 1 1 d . . . . .
H8A H 0.7911 -0.2151 0.2435 0.043 Uiso 1 1 calc R U . . .
H8B H 0.6077 -0.0777 0.2554 0.043 Uiso 1 1 calc R U . . .
H8C H 0.8213 -0.0259 0.2296 0.043 Uiso 1 1 calc R U . . .
C9 C 1.1548(7) -0.1033(5) 0.28410(11) 0.0284(9) Uani 1 1 d . . . . .
H9A H 1.1707 -0.2209 0.2769 0.043 Uiso 1 1 calc R U . . .
H9B H 1.2244 -0.0330 0.2642 0.043 Uiso 1 1 calc R U . . .
H9C H 1.2300 -0.0838 0.3090 0.043 Uiso 1 1 calc R U . . .
C10 C 0.4066(7) -0.0120(6) 0.43618(10) 0.0270(9) Uani 1 1 d . . . . .
H10A H 0.3055 -0.1062 0.4295 0.032 Uiso 1 1 calc R U . . .
H10B H 0.3299 0.0932 0.4289 0.032 Uiso 1 1 calc R U . . .
C11 C 0.4573(7) -0.0129(5) 0.47990(10) 0.0225(8) Uani 1 1 d . . . . .
C12 C 0.6536(7) 0.0631(5) 0.49539(11) 0.0274(9) Uani 1 1 d . . . . .
H12 H 0.7586 0.1164 0.4787 0.033 Uiso 1 1 calc R U . . .
C13 C 0.6928(8) 0.0596(6) 0.53590(11) 0.0321(9) Uani 1 1 d . . . . .
H13 H 0.8255 0.1092 0.5462 0.039 Uiso 1 1 calc R U . . .
C14 C 0.5355(7) -0.0174(6) 0.56107(11) 0.0311(9) Uani 1 1 d . . . . .
H14 H 0.5621 -0.0192 0.5882 0.037 Uiso 1 1 calc R U . . .
C15 C 0.3380(8) -0.0917(5) 0.54556(11) 0.0288(9) Uani 1 1 d . . . . .
H15 H 0.2311 -0.1428 0.5623 0.035 Uiso 1 1 calc R U . . .
C16 C 0.3006(7) -0.0895(5) 0.50501(11) 0.0265(9) Uani 1 1 d . . . . .
H16 H 0.1688 -0.1401 0.4946 0.032 Uiso 1 1 calc R U . . .
HO4 H 0.840(9) 0.610(7) 0.3264(13) 0.039(13) 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
O1 C2 1.427(4) . ?
O1 C7 1.447(4) . ?
O2 C7 1.414(4) . ?
O2 C1 1.434(4) . ?
O3 C3 1.412(4) . ?
O3 C4 1.447(4) . ?
O4 C5 1.427(5) . ?
O4 HO4 0.95(5) . ?
O5 C3 1.417(4) . ?
O5 C10 1.433(4) . ?
C1 C4 1.520(5) . ?
C1 C2 1.553(5) . ?
C1 H1 0.9800 . ?
C2 C3 1.522(5) . ?
C2 H2 0.9800 . ?
C3 H3 0.9800 . ?
C4 C5 1.515(5) . ?
C4 H4 0.9800 . ?
C5 C6 1.509(5) . ?
C5 H5 0.9800 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C9 1.503(5) . ?
C7 C8 1.506(5) . ?
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 C11 1.508(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C16 1.381(5) . ?
C11 C12 1.388(6) . ?
C12 C13 1.389(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.387(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.388(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.389(5) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?

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
C2 O1 C7 107.8(3) . . ?
C7 O2 C1 107.7(3) . . ?
C3 O3 C4 106.0(3) . . ?
C5 O4 HO4 112(3) . . ?
C3 O5 C10 112.4(3) . . ?
O2 C1 C4 110.3(3) . . ?
O2 C1 C2 103.0(3) . . ?
C4 C1 C2 103.4(3) . . ?
O2 C1 H1 113.1 . . ?
C4 C1 H1 113.1 . . ?
C2 C1 H1 113.1 . . ?
O1 C2 C3 109.7(3) . . ?
O1 C2 C1 105.1(3) . . ?
C3 C2 C1 104.1(3) . . ?
O1 C2 H2 112.5 . . ?
C3 C2 H2 112.5 . . ?
C1 C2 H2 112.5 . . ?
O3 C3 O5 111.9(3) . . ?
O3 C3 C2 106.3(3) . . ?
O5 C3 C2 106.9(3) . . ?
O3 C3 H3 110.5 . . ?
O5 C3 H3 110.5 . . ?
C2 C3 H3 110.5 . . ?
O3 C4 C5 109.6(3) . . ?
O3 C4 C1 104.0(3) . . ?
C5 C4 C1 115.6(3) . . ?
O3 C4 H4 109.2 . . ?
C5 C4 H4 109.2 . . ?
C1 C4 H4 109.2 . . ?
O4 C5 C6 111.8(3) . . ?
O4 C5 C4 104.7(3) . . ?
C6 C5 C4 112.2(3) . . ?
O4 C5 H5 109.3 . . ?
C6 C5 H5 109.3 . . ?
C4 C5 H5 109.3 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O2 C7 O1 104.1(3) . . ?
O2 C7 C9 111.7(3) . . ?
O1 C7 C9 110.2(3) . . ?
O2 C7 C8 109.5(3) . . ?
O1 C7 C8 108.0(3) . . ?
C9 C7 C8 113.0(3) . . ?
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 . . ?
O5 C10 C11 108.7(3) . . ?
O5 C10 H10A 109.9 . . ?
C11 C10 H10A 109.9 . . ?
O5 C10 H10B 109.9 . . ?
C11 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
C16 C11 C12 119.6(4) . . ?
C16 C11 C10 118.5(4) . . ?
C12 C11 C10 121.9(3) . . ?
C11 C12 C13 119.9(4) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C14 C13 C12 120.4(4) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 119.6(3) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C16 119.8(4) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C11 C16 C15 120.7(4) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?

_refine_diff_density_max         0.299
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.068

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_145
_database_code_depnum_ccdc_archive 'CCDC 1545187'
_audit_update_record             
;
2017-04-20 deposited with the CCDC.
2017-10-11 downloaded from the CCDC.
;

#------------------ AUDIT DETAILS -------------------------------------------#

_audit_creation_date             
;
'Tue Dec 13 14:03:15 2016'
;
_audit_creation_method           SHELXL-2014/6

_chemical_name_systematic        
(2S,3R,4S,5R)-3-hydroxy-4,5-O-(1-methylethylidene)-2-methyl-piperidine
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H17 N O3'
_chemical_formula_sum            'C9 H17 N O3'
_chemical_formula_weight         187.23

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'

_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.5000(2)
_cell_length_b                   9.8160(3)
_cell_length_c                   18.5860(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1003.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1516
_cell_measurement_theta_min      4.758
_cell_measurement_theta_max      70.649

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_F_000             408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.87478
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_probe          x-ray
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Onyx
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.1241
_diffrn_reflns_number            2631
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.758
_diffrn_reflns_theta_max         70.649
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measured_fraction_theta_full 0.940
_diffrn_reflns_Laue_measured_fraction_max 0.908
_diffrn_reflns_point_group_measured_fraction_max 0.784
_reflns_number_total             1516
_reflns_number_gt                1228
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.445
_reflns_Friedel_fraction_max     0.600
_reflns_Friedel_fraction_full    0.633

_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -70.00   23.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -46.2824   57.0000  -30.0000 93

#__ type_ start__ end____ width___ exp.time_
  2 omega   73.00  118.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       46.2824  125.0000  -30.0000 45

#__ type_ start__ end____ width___ exp.time_
  3 omega   28.00   77.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -45.0000  -60.0000 49

#__ type_ start__ end____ width___ exp.time_
  4 omega   24.00   69.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -30.0000  150.0000 45

#__ type_ start__ end____ width___ exp.time_
  5 omega   24.00   69.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -30.0000  -30.0000 45

#__ type_ start__ end____ width___ exp.time_
  6 omega   24.00   69.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -30.0000   30.0000 45

#__ type_ start__ end____ width___ exp.time_
  7 omega   24.00   69.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -30.0000 -120.0000 45
;

_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_structure_solution    'SIR2004 J.Appl.Cryst.38,381-388'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_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)+(0.0372P)²] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 341 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(1)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         1516
_refine_ls_number_parameters     122
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.0882
_refine_ls_wR_factor_gt          0.0828
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_restrained_S_all      0.984
_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
N1 N 0.6994(4) 1.1156(3) 0.45449(14) 0.0179(5) Uani 1 1 d . . . . .
O1 O 0.6690(3) 0.8392(2) 0.39757(11) 0.0219(5) Uani 1 1 d . . . . .
O2 O 0.9832(3) 0.8784(2) 0.32205(10) 0.0218(5) Uani 1 1 d . . . . .
O3 O 1.2123(3) 1.1342(2) 0.44684(11) 0.0224(5) Uani 1 1 d . . . . .
H3A H 1.3496 1.1016 0.4477 0.034 Uiso 1 1 calc R U . . .
C1 C 0.8307(5) 1.1437(3) 0.38669(16) 0.0189(6) Uani 1 1 d . . . . .
H1 H 0.7394 1.1008 0.3475 0.023 Uiso 1 1 calc R U . . .
C2 C 1.0846(5) 1.0823(3) 0.38702(16) 0.0187(6) Uani 1 1 d . . . . .
H2 H 1.1696 1.1080 0.3427 0.022 Uiso 1 1 calc R U . . .
C3 C 1.0627(5) 0.9267(3) 0.39088(16) 0.0190(6) Uani 1 1 d . . . . .
H3 H 1.2194 0.8858 0.4037 0.023 Uiso 1 1 calc R U . . .
C4 C 0.8635(5) 0.8804(3) 0.44379(16) 0.0194(6) Uani 1 1 d . . . . .
H4 H 0.9210 0.8024 0.4720 0.023 Uiso 1 1 calc R U . . .
C5 C 0.7754(5) 0.9914(3) 0.49326(16) 0.0205(6) Uani 1 1 d . . . . .
H5A H 0.6391 0.9574 0.5211 0.025 Uiso 1 1 calc R U . . .
H5B H 0.9045 1.0146 0.5266 0.025 Uiso 1 1 calc R U . . .
C6 C 0.8315(6) 1.2967(3) 0.37330(17) 0.0232(7) Uani 1 1 d . . . . .
H6A H 0.9165 1.3158 0.3293 0.035 Uiso 1 1 calc R U . . .
H6B H 0.6672 1.3289 0.3696 0.035 Uiso 1 1 calc R U . . .
H6C H 0.9114 1.3419 0.4125 0.035 Uiso 1 1 calc R U . . .
C7 C 0.7749(5) 0.7946(3) 0.33160(16) 0.0208(7) Uani 1 1 d . . . . .
C8 C 0.5958(5) 0.8216(4) 0.27177(18) 0.0271(8) Uani 1 1 d . . . . .
H8A H 0.4551 0.7651 0.2782 0.041 Uiso 1 1 calc R U . . .
H8B H 0.5482 0.9157 0.2728 0.041 Uiso 1 1 calc R U . . .
H8C H 0.6704 0.8013 0.2263 0.041 Uiso 1 1 calc R U . . .
C9 C 0.8482(7) 0.6461(3) 0.33625(19) 0.0332(8) Uani 1 1 d . . . . .
H9A H 0.7057 0.5909 0.3427 0.050 Uiso 1 1 calc R U . . .
H9B H 0.9293 0.6199 0.2927 0.050 Uiso 1 1 calc R U . . .
H9C H 0.9558 0.6333 0.3763 0.050 Uiso 1 1 calc R U . . .
HN1 H 0.719(6) 1.186(4) 0.478(2) 0.027(10) 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
N1 C5 1.476(4) . ?
N1 C1 1.478(4) . ?
N1 HN1 0.83(4) . ?
O1 C7 1.426(4) . ?
O1 C4 1.430(3) . ?
O2 C7 1.421(4) . ?
O2 C3 1.433(3) . ?
O3 C2 1.410(4) . ?
O3 H3A 0.8200 . ?
C1 C2 1.521(4) . ?
C1 C6 1.523(4) . ?
C1 H1 0.9800 . ?
C2 C3 1.534(4) . ?
C2 H2 0.9800 . ?
C3 C4 1.541(4) . ?
C3 H3 0.9800 . ?
C4 C5 1.506(4) . ?
C4 H4 0.9800 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.509(4) . ?
C7 C9 1.515(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

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
C5 N1 C1 115.6(2) . . ?
C5 N1 HN1 113(2) . . ?
C1 N1 HN1 104(2) . . ?
C7 O1 C4 107.3(2) . . ?
C7 O2 C3 109.0(2) . . ?
C2 O3 H3A 109.5 . . ?
N1 C1 C2 111.8(2) . . ?
N1 C1 C6 109.0(2) . . ?
C2 C1 C6 112.9(3) . . ?
N1 C1 H1 107.7 . . ?
C2 C1 H1 107.7 . . ?
C6 C1 H1 107.7 . . ?
O3 C2 C1 108.5(2) . . ?
O3 C2 C3 111.2(2) . . ?
C1 C2 C3 108.8(2) . . ?
O3 C2 H2 109.4 . . ?
C1 C2 H2 109.4 . . ?
C3 C2 H2 109.4 . . ?
O2 C3 C2 108.2(2) . . ?
O2 C3 C4 104.8(2) . . ?
C2 C3 C4 112.3(2) . . ?
O2 C3 H3 110.5 . . ?
C2 C3 H3 110.5 . . ?
C4 C3 H3 110.5 . . ?
O1 C4 C5 109.3(2) . . ?
O1 C4 C3 103.4(2) . . ?
C5 C4 C3 113.9(3) . . ?
O1 C4 H4 110.0 . . ?
C5 C4 H4 110.0 . . ?
C3 C4 H4 110.0 . . ?
N1 C5 C4 113.0(2) . . ?
N1 C5 H5A 109.0 . . ?
C4 C5 H5A 109.0 . . ?
N1 C5 H5B 109.0 . . ?
C4 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O2 C7 O1 105.0(2) . . ?
O2 C7 C8 109.4(2) . . ?
O1 C7 C8 108.2(2) . . ?
O2 C7 C9 110.5(2) . . ?
O1 C7 C9 110.8(3) . . ?
C8 C7 C9 112.6(3) . . ?
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 . . ?

_refine_diff_density_max         0.163
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.046

_shelxl_version_number           2014/6

