# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2015

####################################################################### 
# 
# 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_klb008_0m
_database_code_depnum_ccdc_archive 'CCDC 1028235'
_audit_update_record             
;
2014-10-08 deposited with the CCDC.
2015-03-13 downloaded from the CCDC.
;
_audit_creation_date             2013-12-18
_audit_creation_method           
; 
Olex2 1.2 
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736) 
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
; 
(3RS, 4RS)-N-methoxy-3-chloro-4-hydroxy-2,3,4,7-tetrahydro-1H-azepine  
;
_chemical_formula_moiety         'C7 H12 Cl N O2'
_chemical_formula_sum            'C7 H7 Cl N O2'
_chemical_formula_weight         172.59
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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. 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   24.849(3)
_cell_length_b                   4.7231(5)
_cell_length_c                   14.8643(17)
_cell_angle_alpha                90
_cell_angle_beta                 103.467(2)
_cell_angle_gamma                90
_cell_volume                     1696.6(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1920
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.57
_cell_measurement_theta_min      2.82
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.939
_exptl_absorpt_coefficient_mu    0.400
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6525
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0697 before and 0.0500 after correction.'
_exptl_crystal_colour            Clear
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.159
_exptl_crystal_size_mid          0.063
_exptl_crystal_size_min          0.057
_exptl_special_details           
; 
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12847
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.426
_diffrn_reflns_theta_min         1.685
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1287
_reflns_number_total             1736
_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. 
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.894
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     106
_refine_ls_number_reflns         1736
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0562
_refine_ls_restrained_S_all      0.998
_refine_ls_shift/su_max          0.043
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1475P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1727
_refine_ls_wR_factor_ref         0.1969
_refine_special_details          
; 
 ? 
;
_olex2_refinement_description    
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups, All C(H,H) groups 
 At 1.5 times of: 
  All C(H,H,H,H,H,H) groups, All O(H) groups 
2. Uiso/Uaniso restraints and constraints 
O2 \\sim O2A: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 
0.08 
3. Others 
 Sof(H7BD)=Sof(H7BE)=Sof(H7BF)=Sof(O2A)=1-FVAR(1) 
 Sof(H7AA)=Sof(H7AB)=Sof(H7AC)=Sof(O2)=FVAR(1) 
4.a Ternary CH refined with riding coordinates: 
 C2(H2), C3(H3) 
4.b Secondary CH2 refined with riding coordinates: 
 C1(H1A,H1B), C6(H6A,H6B) 
4.c Me refined with riding coordinates: 
 C7(H7AA,H7AB,H7AC), C7(H7BD,H7BE,H7BF) 
4.d Aromatic/amide H refined with riding coordinates: 
 C4(H4), C5(H5) 
4.e Idealised tetrahedral OH refined as rotating group: 
 O1(H1) 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.08770(12) 0.2535(8) 0.3000(2) 0.0292(8) Uani 1 1 d . . . . .
H1A H 0.0545 0.2680 0.2483 0.035 Uiso 1 1 calc R . . . .
H1B H 0.0896 0.0576 0.3242 0.035 Uiso 1 1 calc R . . . .
C2 C 0.13908(13) 0.3129(7) 0.2639(2) 0.0245(7) Uani 1 1 d . . . . .
H2 H 0.1399 0.5176 0.2470 0.029 Uiso 1 1 calc R . . . .
C3 C 0.19353(11) 0.2335(6) 0.3300(2) 0.0240(7) Uani 1 1 d . . . . .
H3 H 0.1903 0.0377 0.3538 0.029 Uiso 1 1 calc R . . . .
C4 C 0.20721(13) 0.4348(7) 0.4106(3) 0.0323(8) Uani 1 1 d . . . . .
H4 H 0.2418 0.5296 0.4205 0.039 Uiso 1 1 calc R . . . .
C5 C 0.17610(13) 0.4926(8) 0.4687(2) 0.0337(8) Uani 1 1 d . . . . .
H5 H 0.1906 0.6197 0.5179 0.040 Uiso 1 1 calc R . . . .
C6 C 0.11953(14) 0.3740(9) 0.4634(2) 0.0370(9) Uani 1 1 d . . . . .
H6A H 0.1217 0.1653 0.4695 0.044 Uiso 1 1 calc R . . . .
H6B H 0.1047 0.4498 0.5149 0.044 Uiso 1 1 calc R . . . .
C7 C 0.00389(16) 0.6798(8) 0.3918(3) 0.0422(9) Uani 1 1 d . . . . .
H7AA H -0.0116 0.7566 0.3299 0.063 Uiso 0.812(6) 1 calc R . P A 1
H7AB H 0.0328 0.8070 0.4255 0.063 Uiso 0.812(6) 1 calc R . P A 1
H7AC H -0.0255 0.6627 0.4255 0.063 Uiso 0.812(6) 1 calc R . P A 1
H7BD H -0.0243 0.6959 0.3336 0.063 Uiso 0.188(6) 1 calc R . P A 2
H7BE H 0.0046 0.8542 0.4277 0.063 Uiso 0.188(6) 1 calc R . P A 2
H7BF H -0.0050 0.5191 0.4275 0.063 Uiso 0.188(6) 1 calc R . P A 2
N1 N 0.08208(12) 0.4515(9) 0.3737(2) 0.0439(9) Uani 1 1 d . . . . .
O1 O 0.23903(9) 0.2427(5) 0.28708(19) 0.0377(7) Uani 1 1 d . . . . .
H1 H 0.2420 0.0859 0.2620 0.057 Uiso 1 1 calc GR . . . .
O2 O 0.02713(10) 0.4074(6) 0.3837(2) 0.0287(9) Uani 0.812(6) 1 d . . P A 1
O2A O 0.0632(5) 0.631(3) 0.3697(8) 0.026(3) Uiso 0.188(6) 1 d . . P A 2
Cl1 Cl 0.13106(3) 0.09809(18) 0.16058(5) 0.0327(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 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.522(4) . ?
C1 N1 1.471(4) . ?
C2 H2 1.0000 . ?
C2 C3 1.523(4) . ?
C2 Cl1 1.812(3) . ?
C3 H3 1.0000 . ?
C3 C4 1.505(5) . ?
C3 O1 1.423(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.315(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.498(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 N1 1.484(5) . ?
C7 H7AA 0.9800 . ?
C7 H7AB 0.9800 . ?
C7 H7AC 0.9800 . ?
C7 H7BD 0.9800 . ?
C7 H7BE 0.9800 . ?
C7 H7BF 0.9800 . ?
C7 O2 1.426(4) . ?
C7 O2A 1.598(13) . ?
N1 O2 1.423(4) . ?
N1 O2A 0.964(12) . ?
O1 H1 0.8400 . ?

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
H1A C1 H1B 107.9 . . ?
C2 C1 H1A 109.2 . . ?
C2 C1 H1B 109.2 . . ?
N1 C1 H1A 109.2 . . ?
N1 C1 H1B 109.1 . . ?
N1 C1 C2 112.3(3) . . ?
C1 C2 H2 109.5 . . ?
C1 C2 Cl1 105.1(2) . . ?
C3 C2 C1 114.8(3) . . ?
C3 C2 H2 109.5 . . ?
C3 C2 Cl1 108.4(2) . . ?
Cl1 C2 H2 109.5 . . ?
C2 C3 H3 108.9 . . ?
C4 C3 C2 111.1(2) . . ?
C4 C3 H3 108.9 . . ?
O1 C3 C2 112.5(3) . . ?
O1 C3 H3 108.9 . . ?
O1 C3 C4 106.4(2) . . ?
C3 C4 H4 116.7 . . ?
C5 C4 C3 126.6(3) . . ?
C5 C4 H4 116.7 . . ?
C4 C5 H5 117.4 . . ?
C4 C5 C6 125.1(3) . . ?
C6 C5 H5 117.4 . . ?
C5 C6 H6A 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
N1 C6 C5 109.8(3) . . ?
N1 C6 H6A 109.7 . . ?
N1 C6 H6B 109.7 . . ?
H7AA C7 H7AB 109.5 . . ?
H7AA C7 H7AC 109.5 . . ?
H7AB C7 H7AC 109.5 . . ?
H7BD C7 H7BE 109.5 . . ?
H7BD C7 H7BF 109.5 . . ?
H7BE C7 H7BF 109.5 . . ?
O2 C7 H7AA 109.5 . . ?
O2 C7 H7AB 109.5 . . ?
O2 C7 H7AC 109.5 . . ?
O2A C7 H7BD 109.5 . . ?
O2A C7 H7BE 109.5 . . ?
O2A C7 H7BF 109.5 . . ?
C1 N1 C6 111.4(3) . . ?
O2 N1 C1 104.2(3) . . ?
O2 N1 C6 106.6(3) . . ?
O2A N1 C1 130.0(8) . . ?
O2A N1 C6 117.8(8) . . ?
C3 O1 H1 109.5 . . ?
C7 O2 N1 107.1(3) . . ?
N1 O2A C7 125.0(11) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 Cl1 0.84 2.82 2.975(3) 92.5 .

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -71.9(3) . . . . ?
C1 C2 C3 O1 169.0(3) . . . . ?
C1 N1 O2 C7 -136.7(3) . . . . ?
C1 N1 O2A C7 101.7(11) . . . . ?
C2 C1 N1 C6 -78.1(4) . . . . ?
C2 C1 N1 O2 167.3(3) . . . . ?
C2 C1 N1 O2A 90.8(10) . . . . ?
C2 C3 C4 C5 56.7(4) . . . . ?
C3 C4 C5 C6 -2.2(6) . . . . ?
C4 C5 C6 N1 -59.3(5) . . . . ?
C5 C6 N1 C1 83.6(4) . . . . ?
C5 C6 N1 O2 -163.4(3) . . . . ?
C5 C6 N1 O2A -86.8(9) . . . . ?
C6 N1 O2 C7 105.5(3) . . . . ?
C6 N1 O2A C7 -89.9(11) . . . . ?
N1 C1 C2 C3 72.1(4) . . . . ?
N1 C1 C2 Cl1 -169.0(2) . . . . ?
O1 C3 C4 C5 179.4(3) . . . . ?
O2 C7 O2A N1 -10.4(9) . . . . ?
O2 N1 O2A C7 9.2(8) . . . . ?
O2A C7 O2 N1 6.0(5) . . . . ?
O2A N1 O2 C7 -8.8(8) . . . . ?
Cl1 C2 C3 C4 171.0(2) . . . . ?
Cl1 C2 C3 O1 51.9(3) . . . . ?
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# 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_klb009_0m
_database_code_depnum_ccdc_archive 'CCDC 1028236'
_audit_update_record             
;
2014-10-08 deposited with the CCDC.
2015-03-13 downloaded from the CCDC.
;
_audit_creation_date             2014-08-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
(2RS, 3RS)-N-phenylmethoxy-2-hydroxymethyl-3-hydroxy-1,2,3,6-tetrahydropyridine  
;
_chemical_formula_moiety         '2(C13 H17 N O3)'
_chemical_formula_sum            'C26 H34 N2 O6'
_chemical_formula_weight         470.55
_chemical_melting_point          ?
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'

_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. 
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.9549(4)
_cell_length_b                   11.3328(5)
_cell_length_c                   11.8818(5)
_cell_angle_alpha                106.4607(7)
_cell_angle_beta                 101.6175(7)
_cell_angle_gamma                100.1738(7)
_cell_volume                     1219.60(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4823
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.174
_cell_measurement_theta_min      2.192
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0517 before and 0.0460 after correction. The Ratio of minimum to maximum transmission is 0.9654. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            Clear
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.161
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.072
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            23662
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.413
_diffrn_reflns_theta_min         1.854
_diffrn_ambient_temperature      99.65
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3483
_reflns_number_total             5015
_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. 
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         5015
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0367
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.175
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0273P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0677
_refine_ls_wR_factor_ref         0.0727
_refine_special_details          
;
 ? 
;
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H14A(0.029) H14B(0.029) H15(0.031) H16(0.03) H17(0.024)
 H18(0.022) H19A(0.026) H19B(0.026) H20A(0.028) H20B(0.028) H22(0.035)
 H23(0.045) H24(0.046) H25(0.04) H26(0.03) H1A(0.03) H1B(0.03) H2(0.036)
 H3(0.038) H4A(0.031) H5A(0.026) H6A(0.033) H6B(0.033) H7A(0.036) H7B(0.036)
 H9(0.033) H10(0.034) H11(0.033) H12(0.033) H13(0.028) H1(0.045) H2A(0.065)
 Fixed X: H14A(0.3431) H14B(0.1777) H15(0.2632) H16(0.1516) H17(-0.0057)
 H18(0.0141) H19A(0.1147) H19B(0.048) H20A(0.4253) H20B(0.3175) H22(0.2067)
 H23(0.2006) H24(0.3232) H25(0.4554) H26(0.461) H1A(0.2342) H1B(0.0812)
 H2(0.1198) H3(0.2566) H4A(0.4566) H5A(0.4378) H6A(0.4832) H6B(0.4166)
 H7A(0.1741) H7B(0.0606) H9(0.3978) H10(0.4288) H11(0.2319) H12(0.0046) H13(-
 0.0266) H1(0.2377) H2A(0.612)
 Fixed Y: H14A(0.9979) H14B(0.9827) H15(1.0693) H16(0.9228) H17(0.7413)
 H18(0.7911) H19A(0.5659) H19B(0.6043) H20A(0.7941) H20B(0.6556) H22(0.559)
 H23(0.5568) H24(0.7325) H25(0.9108) H26(0.9139) H1A(0.0054) H1B(0.0351) H2(-
 0.0221) H3(0.1261) H4A(0.2609) H5A(0.1685) H6A(0.3447) H6B(0.425) H7A(0.3455)
 H7B(0.214) H9(0.3369) H10(0.3821) H11(0.3603) H12(0.2916) H13(0.2422)
 H1(0.3589) H2A(0.4703)
 Fixed Z: H14A(0.3874) H14B(0.3784) H15(0.2232) H16(0.0413) H17(0.0468)
 H18(0.2502) H19A(0.1807) H19B(0.2943) H20A(0.4613) H20B(0.4021) H22(0.5312)
 H23(0.7257) H24(0.8953) H25(0.8714) H26(0.6774) H1A(0.6559) H1B(0.6436)
 H2(0.8224) H3(0.9956) H4A(0.9772) H5A(0.7732) H6A(0.7053) H6B(0.8045)
 H7A(0.6153) H7B(0.5352) H9(0.4891) H10(0.3155) H11(0.159) H12(0.1768)
 H13(0.3487) H1(0.9199) H2A(0.9247)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
C14 C 0.24653(14) 0.95327(12) 0.33439(12) 0.0244(3) Uani 1 1 d . . . . .
H14A H 0.3431 0.9979 0.3874 0.029 Uiso 1 1 calc R U . . .
H14B H 0.1777 0.9827 0.3784 0.029 Uiso 1 1 calc R U . . .
C15 C 0.22631(14) 0.98457(13) 0.21922(12) 0.0260(3) Uani 1 1 d . . . . .
H15 H 0.2632 1.0693 0.2232 0.031 Uiso 1 1 calc R U . . .
C16 C 0.15896(14) 0.89849(13) 0.11209(12) 0.0246(3) Uani 1 1 d . . . . .
H16 H 0.1516 0.9228 0.0413 0.030 Uiso 1 1 calc R U . . .
C17 C 0.09385(13) 0.76385(12) 0.09841(11) 0.0200(3) Uani 1 1 d . . . . .
H17 H -0.0057 0.7413 0.0468 0.024 Uiso 1 1 calc R U . . .
C18 C 0.08686(13) 0.74885(12) 0.22143(11) 0.0182(3) Uani 1 1 d . . . . .
H18 H 0.0141 0.7911 0.2502 0.022 Uiso 1 1 calc R U . . .
C19 C 0.04665(13) 0.61091(12) 0.21281(12) 0.0216(3) Uani 1 1 d . . . . .
H19A H 0.1147 0.5659 0.1807 0.026 Uiso 1 1 calc R U . . .
H19B H 0.0480 0.6043 0.2943 0.026 Uiso 1 1 calc R U . . .
C20 C 0.33346(13) 0.74222(13) 0.45988(11) 0.0232(3) Uani 1 1 d . . . . .
H20A H 0.4253 0.7941 0.4613 0.028 Uiso 1 1 calc R U . . .
H20B H 0.3175 0.6556 0.4021 0.028 Uiso 1 1 calc R U . . .
C21 C 0.33341(13) 0.73745(13) 0.58474(12) 0.0197(3) Uani 1 1 d . . . . .
C22 C 0.25700(14) 0.63122(14) 0.60018(14) 0.0292(4) Uani 1 1 d . . . . .
H22 H 0.2067 0.5590 0.5312 0.035 Uiso 1 1 calc R U . . .
C23 C 0.25356(15) 0.62980(16) 0.71582(15) 0.0374(4) Uani 1 1 d . . . . .
H23 H 0.2006 0.5568 0.7257 0.045 Uiso 1 1 calc R U . . .
C24 C 0.32638(15) 0.73353(17) 0.81626(14) 0.0384(4) Uani 1 1 d . . . . .
H24 H 0.3232 0.7325 0.8953 0.046 Uiso 1 1 calc R U . . .
C25 C 0.40413(15) 0.83922(15) 0.80202(13) 0.0335(4) Uani 1 1 d . . . . .
H25 H 0.4554 0.9108 0.8714 0.040 Uiso 1 1 calc R U . . .
C26 C 0.40734(13) 0.84087(13) 0.68672(12) 0.0248(3) Uani 1 1 d . . . . .
H26 H 0.4610 0.9139 0.6774 0.030 Uiso 1 1 calc R U . . .
N2 N 0.22659(11) 0.81598(10) 0.30796(9) 0.0194(3) Uani 1 1 d . . . . .
O4 O 0.16671(11) 0.67957(9) 0.03488(8) 0.0259(2) Uani 1 1 d . . . . .
O5 O -0.09246(10) 0.55585(10) 0.13265(9) 0.0289(3) Uani 1 1 d . . . . .
O6 O 0.22066(9) 0.79852(8) 0.42403(7) 0.0212(2) Uani 1 1 d . . . . .
C1 C 0.17966(14) 0.06159(12) 0.69574(12) 0.0247(3) Uani 1 1 d . . . . .
H1A H 0.2342 0.0054 0.6559 0.030 Uiso 1 1 calc R U . . .
H1B H 0.0812 0.0351 0.6436 0.030 Uiso 1 1 calc R U . . .
C2 C 0.18046(15) 0.05027(13) 0.81791(13) 0.0302(4) Uani 1 1 d . . . . .
H2 H 0.1198 -0.0221 0.8224 0.036 Uiso 1 1 calc R U . . .
C3 C 0.26222(16) 0.13701(14) 0.92013(13) 0.0317(4) Uani 1 1 d . . . . .
H3 H 0.2566 0.1261 0.9956 0.038 Uiso 1 1 calc R U . . .
C4 C 0.36329(15) 0.25177(13) 0.92065(12) 0.0258(3) Uani 1 1 d . . . . .
H4A H 0.4566 0.2609 0.9772 0.031 Uiso 1 1 calc R U . . .
C5 C 0.38590(13) 0.23619(12) 0.79421(11) 0.0218(3) Uani 1 1 d . . . . .
H5A H 0.4378 0.1685 0.7732 0.026 Uiso 1 1 calc R U . . .
C6 C 0.46915(13) 0.35837(13) 0.78774(12) 0.0274(3) Uani 1 1 d . . . . .
H6A H 0.4832 0.3447 0.7053 0.033 Uiso 1 1 calc R U . . .
H6B H 0.4166 0.4250 0.8045 0.033 Uiso 1 1 calc R U . . .
C7 C 0.15912(14) 0.26301(14) 0.55099(12) 0.0302(4) Uani 1 1 d . . . . .
H7A H 0.1741 0.3455 0.6153 0.036 Uiso 1 1 calc R U . . .
H7B H 0.0606 0.2140 0.5352 0.036 Uiso 1 1 calc R U . . .
C8 C 0.18228(14) 0.28501(13) 0.43677(12) 0.0223(3) Uani 1 1 d . . . . .
C9 C 0.31741(14) 0.32696(13) 0.42540(12) 0.0272(3) Uani 1 1 d . . . . .
H9 H 0.3978 0.3369 0.4891 0.033 Uiso 1 1 calc R U . . .
C10 C 0.33603(15) 0.35432(13) 0.32251(13) 0.0280(3) Uani 1 1 d . . . . .
H10 H 0.4288 0.3821 0.3155 0.034 Uiso 1 1 calc R U . . .
C11 C 0.21937(15) 0.34116(13) 0.22960(12) 0.0276(3) Uani 1 1 d . . . . .
H11 H 0.2319 0.3603 0.1590 0.033 Uiso 1 1 calc R U . . .
C12 C 0.08484(15) 0.30015(13) 0.24017(12) 0.0276(3) Uani 1 1 d . . . . .
H12 H 0.0046 0.2916 0.1768 0.033 Uiso 1 1 calc R U . . .
C13 C 0.06633(14) 0.27145(12) 0.34273(12) 0.0237(3) Uani 1 1 d . . . . .
H13 H -0.0266 0.2422 0.3487 0.028 Uiso 1 1 calc R U . . .
N1 N 0.24311(11) 0.19375(10) 0.71031(9) 0.0192(3) Uani 1 1 d . . . . .
O1 O 0.31618(10) 0.36441(9) 0.96608(8) 0.0301(2) Uani 1 1 d . . . . .
H1 H 0.2377 0.3589 0.9199 0.045 Uiso 1 1 calc R U . . .
O2 O 0.60292(10) 0.39753(10) 0.87603(10) 0.0435(3) Uani 1 1 d . . . . .
H2A H 0.6120 0.4703 0.9247 0.065 Uiso 1 1 calc R U . . .
O3 O 0.25597(9) 0.19444(8) 0.59077(7) 0.0221(2) Uani 1 1 d . . . . .
H4 H 0.2418(17) 0.6789(15) 0.0813(14) 0.051(6) Uiso 1 1 d . . . . .
H5 H -0.0990(18) 0.4844(16) 0.0843(15) 0.056(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
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.4928(18) . ?
C14 N2 1.4654(16) . ?
C15 H15 0.9500 . ?
C15 C16 1.3203(18) . ?
C16 H16 0.9500 . ?
C16 C17 1.4974(17) . ?
C17 H17 1.0000 . ?
C17 C18 1.5323(17) . ?
C17 O4 1.4369(15) . ?
C18 H18 1.0000 . ?
C18 C19 1.5120(17) . ?
C18 N2 1.4757(15) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 O5 1.4286(14) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.4999(17) . ?
C20 O6 1.4366(14) . ?
C21 C22 1.3855(18) . ?
C21 C26 1.3837(18) . ?
C22 H22 0.9500 . ?
C22 C23 1.3860(19) . ?
C23 H23 0.9500 . ?
C23 C24 1.374(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.379(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.3821(18) . ?
C26 H26 0.9500 . ?
N2 O6 1.4588(12) . ?
O4 H4 0.837(16) . ?
O5 H5 0.832(16) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.4917(19) . ?
C1 N1 1.4653(16) . ?
C2 H2 0.9500 . ?
C2 C3 1.3216(19) . ?
C3 H3 0.9500 . ?
C3 C4 1.4948(19) . ?
C4 H4A 1.0000 . ?
C4 C5 1.5294(18) . ?
C4 O1 1.4366(15) . ?
C5 H5A 1.0000 . ?
C5 C6 1.5135(18) . ?
C5 N1 1.4702(15) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 O2 1.4267(15) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.5016(18) . ?
C7 O3 1.4305(15) . ?
C8 C9 1.3918(18) . ?
C8 C13 1.3875(17) . ?
C9 H9 0.9500 . ?
C9 C10 1.3824(18) . ?
C10 H10 0.9500 . ?
C10 C11 1.3852(18) . ?
C11 H11 0.9500 . ?
C11 C12 1.3807(19) . ?
C12 H12 0.9500 . ?
C12 C13 1.3851(18) . ?
C13 H13 0.9500 . ?
N1 O3 1.4535(13) . ?
O1 H1 0.8400 . ?
O2 H2A 0.8400 . ?

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
H14A C14 H14B 108.1 . . ?
C15 C14 H14A 109.6 . . ?
C15 C14 H14B 109.6 . . ?
N2 C14 H14A 109.6 . . ?
N2 C14 H14B 109.6 . . ?
N2 C14 C15 110.45(11) . . ?
C14 C15 H15 118.9 . . ?
C16 C15 C14 122.24(13) . . ?
C16 C15 H15 118.9 . . ?
C15 C16 H16 118.9 . . ?
C15 C16 C17 122.23(12) . . ?
C17 C16 H16 118.9 . . ?
C16 C17 H17 107.3 . . ?
C16 C17 C18 111.51(11) . . ?
C18 C17 H17 107.3 . . ?
O4 C17 C16 110.43(10) . . ?
O4 C17 H17 107.3 . . ?
O4 C17 C18 112.60(10) . . ?
C17 C18 H18 108.6 . . ?
C19 C18 C17 112.10(10) . . ?
C19 C18 H18 108.6 . . ?
N2 C18 C17 107.16(10) . . ?
N2 C18 H18 108.6 . . ?
N2 C18 C19 111.69(10) . . ?
C18 C19 H19A 110.2 . . ?
C18 C19 H19B 110.2 . . ?
H19A C19 H19B 108.5 . . ?
O5 C19 C18 107.66(10) . . ?
O5 C19 H19A 110.2 . . ?
O5 C19 H19B 110.2 . . ?
H20A C20 H20B 108.6 . . ?
C21 C20 H20A 110.4 . . ?
C21 C20 H20B 110.4 . . ?
O6 C20 H20A 110.4 . . ?
O6 C20 H20B 110.4 . . ?
O6 C20 C21 106.61(10) . . ?
C22 C21 C20 120.88(13) . . ?
C26 C21 C20 120.31(12) . . ?
C26 C21 C22 118.80(13) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 C21 120.32(14) . . ?
C23 C22 H22 119.8 . . ?
C22 C23 H23 119.9 . . ?
C24 C23 C22 120.30(14) . . ?
C24 C23 H23 119.9 . . ?
C23 C24 H24 120.1 . . ?
C23 C24 C25 119.86(14) . . ?
C25 C24 H24 120.1 . . ?
C24 C25 H25 120.1 . . ?
C24 C25 C26 119.89(14) . . ?
C26 C25 H25 120.1 . . ?
C21 C26 C25 120.82(14) . . ?
C21 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C14 N2 C18 109.55(10) . . ?
O6 N2 C14 103.67(9) . . ?
O6 N2 C18 106.96(9) . . ?
C17 O4 H4 111.5(11) . . ?
C19 O5 H5 111.9(12) . . ?
C20 O6 N2 107.97(8) . . ?
H1A C1 H1B 108.3 . . ?
C2 C1 H1A 109.8 . . ?
C2 C1 H1B 109.8 . . ?
N1 C1 H1A 109.8 . . ?
N1 C1 H1B 109.8 . . ?
N1 C1 C2 109.19(11) . . ?
C1 C2 H2 118.7 . . ?
C3 C2 C1 122.54(14) . . ?
C3 C2 H2 118.7 . . ?
C2 C3 H3 119.0 . . ?
C2 C3 C4 122.00(13) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 H4A 107.8 . . ?
C3 C4 C5 111.16(11) . . ?
C5 C4 H4A 107.8 . . ?
O1 C4 C3 110.80(11) . . ?
O1 C4 H4A 107.8 . . ?
O1 C4 C5 111.44(11) . . ?
C4 C5 H5A 109.2 . . ?
C6 C5 C4 112.03(11) . . ?
C6 C5 H5A 109.2 . . ?
N1 C5 C4 105.42(10) . . ?
N1 C5 H5A 109.2 . . ?
N1 C5 C6 111.74(10) . . ?
C5 C6 H6A 110.0 . . ?
C5 C6 H6B 110.0 . . ?
H6A C6 H6B 108.3 . . ?
O2 C6 C5 108.65(11) . . ?
O2 C6 H6A 110.0 . . ?
O2 C6 H6B 110.0 . . ?
H7A C7 H7B 108.2 . . ?
C8 C7 H7A 109.8 . . ?
C8 C7 H7B 109.8 . . ?
O3 C7 H7A 109.8 . . ?
O3 C7 H7B 109.8 . . ?
O3 C7 C8 109.43(10) . . ?
C9 C8 C7 121.74(12) . . ?
C13 C8 C7 119.48(12) . . ?
C13 C8 C9 118.64(12) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.81(12) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 119.99(13) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.67(13) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.28(13) . . ?
C13 C12 H12 119.9 . . ?
C8 C13 H13 119.7 . . ?
C12 C13 C8 120.60(13) . . ?
C12 C13 H13 119.7 . . ?
C1 N1 C5 110.04(10) . . ?
O3 N1 C1 106.10(9) . . ?
O3 N1 C5 108.29(9) . . ?
C4 O1 H1 109.5 . . ?
C6 O2 H2A 109.5 . . ?
C7 O3 N1 106.43(9) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O5 0.84 1.97 2.7226(13) 148.4 2_566
O2 H2A O1 0.84 1.87 2.6837(13) 164.4 2_667
O4 H4 O2 0.837(16) 1.950(16) 2.7199(14) 152.4(15) 2_666
O5 H5 O4 0.832(16) 1.896(17) 2.7070(14) 164.5(17) 2_565

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 C15 C16 C17 1.9(2) . . . . ?
C14 N2 O6 C20 -120.51(10) . . . . ?
C15 C14 N2 C18 -54.91(13) . . . . ?
C15 C14 N2 O6 -168.80(10) . . . . ?
C15 C16 C17 C18 12.64(18) . . . . ?
C15 C16 C17 O4 -113.35(14) . . . . ?
C16 C17 C18 C19 -169.57(10) . . . . ?
C16 C17 C18 N2 -46.69(14) . . . . ?
C17 C18 C19 O5 -62.84(13) . . . . ?
C17 C18 N2 C14 69.77(12) . . . . ?
C17 C18 N2 O6 -178.49(9) . . . . ?
C18 N2 O6 C20 123.76(10) . . . . ?
C19 C18 N2 C14 -167.10(10) . . . . ?
C19 C18 N2 O6 -55.36(12) . . . . ?
C20 C21 C22 C23 -177.60(12) . . . . ?
C20 C21 C26 C25 177.77(12) . . . . ?
C21 C20 O6 N2 174.53(9) . . . . ?
C21 C22 C23 C24 -0.3(2) . . . . ?
C22 C21 C26 C25 -0.69(19) . . . . ?
C22 C23 C24 C25 -0.5(2) . . . . ?
C23 C24 C25 C26 0.7(2) . . . . ?
C24 C25 C26 C21 -0.1(2) . . . . ?
C26 C21 C22 C23 0.86(19) . . . . ?
N2 C14 C15 C16 18.79(18) . . . . ?
N2 C18 C19 O5 176.88(10) . . . . ?
O4 C17 C18 C19 -44.78(14) . . . . ?
O4 C17 C18 N2 78.09(13) . . . . ?
O6 C20 C21 C22 91.95(14) . . . . ?
O6 C20 C21 C26 -86.48(14) . . . . ?
C1 C2 C3 C4 -1.7(2) . . . . ?
C1 N1 O3 C7 112.31(11) . . . . ?
C2 C1 N1 C5 55.71(14) . . . . ?
C2 C1 N1 O3 172.64(10) . . . . ?
C2 C3 C4 C5 -14.86(19) . . . . ?
C2 C3 C4 O1 109.64(15) . . . . ?
C3 C4 C5 C6 171.02(11) . . . . ?
C3 C4 C5 N1 49.28(14) . . . . ?
C4 C5 C6 O2 58.70(14) . . . . ?
C4 C5 N1 C1 -72.46(12) . . . . ?
C4 C5 N1 O3 171.98(9) . . . . ?
C5 N1 O3 C7 -129.59(11) . . . . ?
C6 C5 N1 C1 165.61(11) . . . . ?
C6 C5 N1 O3 50.05(13) . . . . ?
C7 C8 C9 C10 -175.87(13) . . . . ?
C7 C8 C13 C12 175.27(13) . . . . ?
C8 C7 O3 N1 171.39(10) . . . . ?
C8 C9 C10 C11 0.6(2) . . . . ?
C9 C8 C13 C12 -0.5(2) . . . . ?
C9 C10 C11 C12 -0.3(2) . . . . ?
C10 C11 C12 C13 -0.4(2) . . . . ?
C11 C12 C13 C8 0.8(2) . . . . ?
C13 C8 C9 C10 -0.2(2) . . . . ?
N1 C1 C2 C3 -17.85(19) . . . . ?
N1 C5 C6 O2 176.75(10) . . . . ?
O1 C4 C5 C6 46.89(15) . . . . ?
O1 C4 C5 N1 -74.86(13) . . . . ?
O3 C7 C8 C9 -45.44(18) . . . . ?
O3 C7 C8 C13 138.89(12) . . . . ?
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# 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_klb010_0m
_database_code_depnum_ccdc_archive 'CCDC 1028237'
_audit_update_record             
;
2014-10-08 deposited with the CCDC.
2015-03-13 downloaded from the CCDC.
;
_audit_creation_date             2014-09-24
_audit_creation_method           
; 
Olex2 1.2 
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874) 
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
(2RS,3RS,4SR,5RS)-N-phenylmethoxy-2-hydroxymethyl-3,4,5-trihydroxypiperidine
;
_chemical_formula_moiety         '2(C13 H19 N O5)'
_chemical_formula_sum            'C26 H38 N2 O10'
_chemical_formula_weight         538.58
_chemical_melting_point          ?
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'

_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. 
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.3906(3)
_cell_length_b                   15.9299(9)
_cell_length_c                   17.3564(10)
_cell_angle_alpha                112.4571(11)
_cell_angle_beta                 97.7331(11)
_cell_angle_gamma                99.3952(11)
_cell_volume                     1326.85(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4557
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.890
_cell_measurement_theta_min      2.291
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.960
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0672 before and 0.0526 after correction. The Rat'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.401
_exptl_crystal_size_mid          0.191
_exptl_crystal_size_min          0.176
_exptl_special_details           
; 
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            33786
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.593
_diffrn_reflns_theta_min         1.300
_diffrn_ambient_temperature      99.65
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5491
_reflns_number_total             8134
_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. 
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     376
_refine_ls_number_reflns         8134
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.041
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0710P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1352
_refine_special_details          
; 
 ? 
;
_olex2_refinement_description    
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups 
 At 1.5 times of: 
  All O(H) groups 
2. Others 
 Sof(H7bc)=Sof(H7bd)=Sof(C8A)=Sof(C13A)=Sof(H13A)=Sof(C12A)=Sof(H12A)= 
 Sof(C11A)=Sof(H11A)=Sof(C10A)=Sof(H10A)=Sof(C9A)=Sof(H9A)=1-FVAR(1) 
 Sof(H7aa)=Sof(H7ab)=Sof(C8)=Sof(C9)=Sof(H9)=Sof(C10)=Sof(H10)=Sof(C11)= 
 Sof(H11)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=FVAR(1) 
3.a Ternary CH refined with riding coordinates: 
 C2(H2), C3(H3), C4(H4), C5(H5), C15(H15), C16(H16), C17(H17), C18(H18) 
3.b Secondary CH2 refined with riding coordinates: 
 C1(H1a,H1b), C6(H6a,H6b), C7(H7aa,H7ab), C7(H7bc,H7bd), C14(H14a,H14b), 
 C19(H19a,H19b), C20(H20a,H20b) 
3.c Aromatic/amide H refined with riding coordinates: 
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C13A(H13A), C12A(H12A), 
 C11A(H11A), C10A(H10A), C9A(H9A), C22(H22), C23(H23), C24(H24), C25(H25), 
 C26(H26) 
3.d Fitted hexagon refined as free rotating group: 
 C8(C9,C10,C11,C12,C13), C8A(C13A,C12A,C11A,C10A,C9A), C21(C22,C23,C24,C25,C26) 
3.e Idealised tetrahedral OH refined as rotating group: 
 O2(H2a), O3(H3a), O6(H6), O7(H7), O8(H8), O9(H9b) 
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
H1 H 0.556(4) 0.7056(13) 0.2096(12) 0.033(5) Uiso 1 1 d . . . . .
C1 C 0.3158(2) 0.70588(9) 0.33708(8) 0.0132(3) Uani 1 1 d . . . . .
H1A H 0.1550 0.6567 0.3073 0.016 Uiso 1 1 calc R . . . .
H1B H 0.4588 0.6752 0.3424 0.016 Uiso 1 1 calc R . . . .
C2 C 0.3695(2) 0.76419(9) 0.28602(8) 0.0111(2) Uani 1 1 d . . . . .
H2 H 0.5315 0.8138 0.3167 0.013 Uiso 1 1 calc R . . . .
C3 C 0.1488(2) 0.80931(9) 0.27537(8) 0.0124(3) Uani 1 1 d . . . . .
H3 H 0.1896 0.8499 0.2446 0.015 Uiso 1 1 calc R . . . .
C4 C 0.1108(2) 0.86811(9) 0.36354(8) 0.0127(3) Uani 1 1 d . . . . .
H4 H -0.0415 0.8952 0.3573 0.015 Uiso 1 1 calc R . . . .
C5 C 0.0662(2) 0.80909(9) 0.41462(8) 0.0127(3) Uani 1 1 d . . . . .
H5 H -0.0900 0.7571 0.3824 0.015 Uiso 1 1 calc R . . . .
C6 C 0.0206(2) 0.86720(10) 0.50259(9) 0.0146(3) Uani 1 1 d . . . . .
H6A H -0.0052 0.8277 0.5345 0.017 Uiso 1 1 calc R . . . .
H6B H 0.1734 0.9192 0.5355 0.017 Uiso 1 1 calc R . . . .
C7 C 0.4072(3) 0.73077(11) 0.53965(9) 0.0207(3) Uani 1 1 d . . . . .
H7AA H 0.4349 0.7978 0.5776 0.025 Uiso 0.490(8) 1 calc R . P A 1
H7AB H 0.5737 0.7175 0.5267 0.025 Uiso 0.490(8) 1 calc R . P A 1
H7BC H 0.4335 0.7981 0.5762 0.025 Uiso 0.510(8) 1 calc R . P A 2
H7BD H 0.5737 0.7192 0.5253 0.025 Uiso 0.510(8) 1 calc R . P A 2
C8 C 0.2861(7) 0.66886(19) 0.5799(2) 0.0187(16) Uani 0.490(8) 1 d . . P A 1
C9 C 0.1730(10) 0.7067(2) 0.6489(3) 0.0181(10) Uani 0.490(8) 1 d G . P A 1
H9 H 0.1697 0.7709 0.6706 0.022 Uiso 0.490(8) 1 calc R . P A 1
C10 C 0.0648(10) 0.6505(3) 0.6861(2) 0.0241(11) Uani 0.490(8) 1 d G . P A 1
H10 H -0.0125 0.6763 0.7333 0.029 Uiso 0.490(8) 1 calc R . P A 1
C11 C 0.0696(7) 0.5565(3) 0.6544(2) 0.0216(14) Uani 0.490(8) 1 d G . P A 1
H11 H -0.0043 0.5181 0.6799 0.026 Uiso 0.490(8) 1 calc R . P A 1
C12 C 0.1828(9) 0.5187(2) 0.5855(3) 0.0258(10) Uani 0.490(8) 1 d G . P A 1
H12 H 0.1861 0.4545 0.5638 0.031 Uiso 0.490(8) 1 calc R . P A 1
C13 C 0.2910(9) 0.5749(2) 0.5482(3) 0.0226(9) Uani 0.490(8) 1 d G . P A 1
H13 H 0.3683 0.5490 0.5011 0.027 Uiso 0.490(8) 1 calc R . P A 1
C8A C 0.3163(8) 0.67435(18) 0.5862(2) 0.0177(15) Uani 0.510(8) 1 d . . P A 2
C13A C 0.4092(10) 0.5961(2) 0.5802(3) 0.0239(9) Uani 0.510(8) 1 d G . P A 2
H13A H 0.5442 0.5819 0.5510 0.029 Uiso 0.510(8) 1 calc R . P A 2
C12A C 0.3046(11) 0.5387(2) 0.6168(3) 0.0303(10) Uani 0.510(8) 1 d G . P A 2
H12A H 0.3680 0.4853 0.6127 0.036 Uiso 0.510(8) 1 calc R . P A 2
C11A C 0.1071(7) 0.5595(3) 0.6595(2) 0.0347(19) Uani 0.510(8) 1 d G . P A 2
H11A H 0.0356 0.5203 0.6846 0.042 Uiso 0.510(8) 1 calc R . P A 2
C10A C 0.0142(7) 0.6377(4) 0.6656(3) 0.0280(12) Uani 0.510(8) 1 d G . P A 2
H10A H -0.1208 0.6519 0.6947 0.034 Uiso 0.510(8) 1 calc R . P A 2
C9A C 0.1188(8) 0.6951(3) 0.6289(3) 0.0225(11) Uani 0.510(8) 1 d G . P A 2
H9A H 0.0553 0.7486 0.6330 0.027 Uiso 0.510(8) 1 calc R . P A 2
N1 N 0.2906(2) 0.76796(8) 0.42248(7) 0.0117(2) Uani 1 1 d . . . . .
O1 O 0.39783(18) 0.70549(7) 0.20275(6) 0.0138(2) Uani 1 1 d . . . . .
O2 O -0.08212(17) 0.73953(7) 0.22886(6) 0.0168(2) Uani 1 1 d . . . . .
H2A H -0.0831 0.7188 0.1764 0.025 Uiso 1 1 calc GR . . . .
O3 O 0.33563(17) 0.94157(6) 0.40403(6) 0.0162(2) Uani 1 1 d . . . . .
H3A H 0.2972 0.9893 0.4376 0.024 Uiso 1 1 calc GR . . . .
O4 O -0.20046(18) 0.90372(7) 0.49328(6) 0.0160(2) Uani 1 1 d . . . . .
O5 O 0.21870(18) 0.70522(7) 0.46292(6) 0.0157(2) Uani 1 1 d . . . . .
C14 C 0.3714(2) 0.38340(9) 0.15937(9) 0.0151(3) Uani 1 1 d . . . . .
H14A H 0.5165 0.3689 0.1896 0.018 Uiso 1 1 calc R . . . .
H14B H 0.2714 0.4142 0.2013 0.018 Uiso 1 1 calc R . . . .
C15 C 0.4739(2) 0.44796(9) 0.11899(9) 0.0139(3) Uani 1 1 d . . . . .
H15 H 0.5781 0.4164 0.0780 0.017 Uiso 1 1 calc R . . . .
C16 C 0.2532(2) 0.46922(9) 0.07078(9) 0.0127(3) Uani 1 1 d . . . . .
H16 H 0.3233 0.5047 0.0387 0.015 Uiso 1 1 calc R . . . .
C17 C 0.0665(2) 0.37813(9) 0.00796(8) 0.0126(3) Uani 1 1 d . . . . .
H17 H -0.0875 0.3940 -0.0172 0.015 Uiso 1 1 calc R . . . .
C18 C -0.0254(2) 0.31574(9) 0.05199(9) 0.0129(3) Uani 1 1 d . . . . .
H18 H -0.1140 0.3496 0.0973 0.016 Uiso 1 1 calc R . . . .
C19 C -0.2102(3) 0.22409(10) -0.01235(9) 0.0174(3) Uani 1 1 d . . . . .
H19A H -0.1142 0.1860 -0.0515 0.021 Uiso 1 1 calc R . . . .
H19B H -0.2814 0.1882 0.0186 0.021 Uiso 1 1 calc R . . . .
C20 C 0.2413(3) 0.16479(11) 0.11811(11) 0.0252(3) Uani 1 1 d . . . . .
H20A H 0.4256 0.1897 0.1470 0.030 Uiso 1 1 calc R . . . .
H20B H 0.2286 0.1302 0.0561 0.030 Uiso 1 1 calc R . . . .
C21 C 0.1083(2) 0.10182(7) 0.15419(7) 0.0229(3) Uani 1 1 d . . . . .
C22 C -0.1365(2) 0.04582(8) 0.11168(6) 0.0366(4) Uani 1 1 d G . . . .
H22 H -0.2166 0.0462 0.0596 0.044 Uiso 1 1 calc R . . . .
C23 C -0.26408(19) -0.01067(9) 0.14535(8) 0.0494(6) Uani 1 1 d G . . . .
H23 H -0.4314 -0.0490 0.1163 0.059 Uiso 1 1 calc R . . . .
C24 C -0.1469(2) -0.01116(9) 0.22153(8) 0.0437(5) Uani 1 1 d G . . . .
H24 H -0.2340 -0.0498 0.2445 0.052 Uiso 1 1 calc R . . . .
C25 C 0.0979(2) 0.04484(9) 0.26403(6) 0.0406(5) Uani 1 1 d G . . . .
H25 H 0.1780 0.0445 0.3161 0.049 Uiso 1 1 calc R . . . .
C26 C 0.22547(18) 0.10133(8) 0.23037(7) 0.0337(4) Uani 1 1 d G . . . .
H26 H 0.3928 0.1396 0.2594 0.040 Uiso 1 1 calc R . . . .
N2 N 0.2057(2) 0.29679(8) 0.09131(7) 0.0138(2) Uani 1 1 d . . . . .
O6 O 0.63497(18) 0.53251(7) 0.18379(7) 0.0193(2) Uani 1 1 d . . . . .
H6 H 0.7842 0.5390 0.1743 0.029 Uiso 1 1 calc GR . . . .
O7 O 0.11204(17) 0.52259(6) 0.12707(6) 0.0156(2) Uani 1 1 d . . . . .
H7 H 0.2015 0.5773 0.1555 0.023 Uiso 1 1 calc GR . . . .
O8 O 0.18337(19) 0.33001(7) -0.05982(6) 0.0170(2) Uani 1 1 d . . . . .
H8 H 0.2892 0.3045 -0.0424 0.025 Uiso 1 1 calc GR . . . .
O9 O -0.41699(17) 0.24086(7) -0.06102(6) 0.0168(2) Uani 1 1 d . . . . .
H9B H -0.3680 0.2502 -0.1016 0.025 Uiso 1 1 calc GR . . . .
O10 O 0.11020(18) 0.23903(7) 0.13362(6) 0.0168(2) Uani 1 1 d . . . . .
H4A H -0.333(4) 0.8619(14) 0.4737(12) 0.036(5) 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 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.5303(18) . ?
C1 N1 1.4736(17) . ?
C2 H2 1.0000 . ?
C2 C3 1.5126(18) . ?
C2 O1 1.4354(15) . ?
C3 H3 1.0000 . ?
C3 C4 1.5209(18) . ?
C3 O2 1.4243(15) . ?
C4 H4 1.0000 . ?
C4 C5 1.5323(18) . ?
C4 O3 1.4182(15) . ?
C5 H5 1.0000 . ?
C5 C6 1.5310(18) . ?
C5 N1 1.4813(16) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 O4 1.4253(16) . ?
C7 H7AA 0.9900 . ?
C7 H7AB 0.9900 . ?
C7 H7BC 0.9900 . ?
C7 H7BD 0.9900 . ?
C7 C8 1.526(3) . ?
C7 C8A 1.489(3) . ?
C7 O5 1.4350(16) . ?
C8 C9 1.3900 . ?
C8 C13 1.3900 . ?
C9 H9 0.9500 . ?
C9 C10 1.3900 . ?
C10 H10 0.9500 . ?
C10 C11 1.3900 . ?
C11 H11 0.9500 . ?
C11 C12 1.3900 . ?
C12 H12 0.9500 . ?
C12 C13 1.3900 . ?
C13 H13 0.9500 . ?
C8A C13A 1.3900 . ?
C8A C9A 1.3900 . ?
C13A H13A 0.9500 . ?
C13A C12A 1.3900 . ?
C12A H12A 0.9500 . ?
C12A C11A 1.3900 . ?
C11A H11A 0.9500 . ?
C11A C10A 1.3900 . ?
C10A H10A 0.9500 . ?
C10A C9A 1.3900 . ?
C9A H9A 0.9500 . ?
N1 O5 1.4575(13) . ?
O1 H1 0.842(19) . ?
O2 H2A 0.8400 . ?
O3 H3A 0.8400 . ?
O4 H4A 0.82(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.5243(18) . ?
C14 N2 1.4716(17) . ?
C15 H15 1.0000 . ?
C15 C16 1.5200(18) . ?
C15 O6 1.4251(15) . ?
C16 H16 1.0000 . ?
C16 C17 1.5251(18) . ?
C16 O7 1.4257(16) . ?
C17 H17 1.0000 . ?
C17 C18 1.5293(18) . ?
C17 O8 1.4270(16) . ?
C18 H18 1.0000 . ?
C18 C19 1.5335(18) . ?
C18 N2 1.4695(16) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 O9 1.4297(16) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.5095(17) . ?
C20 O10 1.4324(18) . ?
C21 C22 1.3900 . ?
C21 C26 1.3900 . ?
C22 H22 0.9500 . ?
C22 C23 1.3900 . ?
C23 H23 0.9500 . ?
C23 C24 1.3900 . ?
C24 H24 0.9500 . ?
C24 C25 1.3900 . ?
C25 H25 0.9500 . ?
C25 C26 1.3900 . ?
C26 H26 0.9500 . ?
N2 O10 1.4540(14) . ?
O6 H6 0.8400 . ?
O7 H7 0.8400 . ?
O8 H8 0.8400 . ?
O9 H9B 0.8400 . ?

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
H1A C1 H1B 108.3 . . ?
C2 C1 H1A 109.9 . . ?
C2 C1 H1B 109.9 . . ?
N1 C1 H1A 109.9 . . ?
N1 C1 H1B 109.9 . . ?
N1 C1 C2 108.76(10) . . ?
C1 C2 H2 109.4 . . ?
C3 C2 C1 110.44(10) . . ?
C3 C2 H2 109.4 . . ?
O1 C2 C1 109.92(10) . . ?
O1 C2 H2 109.4 . . ?
O1 C2 C3 108.33(10) . . ?
C2 C3 H3 109.8 . . ?
C2 C3 C4 108.38(10) . . ?
C4 C3 H3 109.8 . . ?
O2 C3 C2 110.20(11) . . ?
O2 C3 H3 109.8 . . ?
O2 C3 C4 108.74(10) . . ?
C3 C4 H4 109.2 . . ?
C3 C4 C5 111.04(11) . . ?
C5 C4 H4 109.2 . . ?
O3 C4 C3 106.47(10) . . ?
O3 C4 H4 109.2 . . ?
O3 C4 C5 111.66(11) . . ?
C4 C5 H5 108.5 . . ?
C6 C5 C4 111.36(11) . . ?
C6 C5 H5 108.5 . . ?
N1 C5 C4 108.96(10) . . ?
N1 C5 H5 108.5 . . ?
N1 C5 C6 111.05(10) . . ?
C5 C6 H6A 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
O4 C6 C5 109.98(10) . . ?
O4 C6 H6A 109.7 . . ?
O4 C6 H6B 109.7 . . ?
H7AA C7 H7AB 109.1 . . ?
H7BC C7 H7BD 108.3 . . ?
C8 C7 H7AA 111.2 . . ?
C8 C7 H7AB 111.2 . . ?
C8A C7 H7BC 109.8 . . ?
C8A C7 H7BD 109.8 . . ?
O5 C7 H7AA 111.2 . . ?
O5 C7 H7AB 111.2 . . ?
O5 C7 H7BC 109.8 . . ?
O5 C7 H7BD 109.8 . . ?
O5 C7 C8 102.87(17) . . ?
O5 C7 C8A 109.19(17) . . ?
C9 C8 C7 120.0(3) . . ?
C9 C8 C13 120.0 . . ?
C13 C8 C7 120.0(3) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.0 . . ?
C13 C12 H12 120.0 . . ?
C8 C13 H13 120.0 . . ?
C12 C13 C8 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13A C8A C7 120.5(3) . . ?
C13A C8A C9A 120.0 . . ?
C9A C8A C7 119.2(3) . . ?
C8A C13A H13A 120.0 . . ?
C8A C13A C12A 120.0 . . ?
C12A C13A H13A 120.0 . . ?
C13A C12A H12A 120.0 . . ?
C13A C12A C11A 120.0 . . ?
C11A C12A H12A 120.0 . . ?
C12A C11A H11A 120.0 . . ?
C12A C11A C10A 120.0 . . ?
C10A C11A H11A 120.0 . . ?
C11A C10A H10A 120.0 . . ?
C9A C10A C11A 120.0 . . ?
C9A C10A H10A 120.0 . . ?
C8A C9A H9A 120.0 . . ?
C10A C9A C8A 120.0 . . ?
C10A C9A H9A 120.0 . . ?
C1 N1 C5 109.79(10) . . ?
O5 N1 C1 104.45(9) . . ?
O5 N1 C5 104.98(9) . . ?
C2 O1 H1 104.0(13) . . ?
C3 O2 H2A 109.5 . . ?
C4 O3 H3A 109.5 . . ?
C6 O4 H4A 111.0(14) . . ?
C7 O5 N1 109.50(9) . . ?
H14A C14 H14B 108.4 . . ?
C15 C14 H14A 110.0 . . ?
C15 C14 H14B 110.0 . . ?
N2 C14 H14A 110.0 . . ?
N2 C14 H14B 110.0 . . ?
N2 C14 C15 108.50(11) . . ?
C14 C15 H15 108.9 . . ?
C14 C15 C16 110.63(10) . . ?
C16 C15 H15 108.9 . . ?
O6 C15 C14 109.53(11) . . ?
O6 C15 H15 108.9 . . ?
O6 C15 C16 110.03(11) . . ?
C15 C16 H16 109.3 . . ?
C15 C16 C17 109.70(11) . . ?
C17 C16 H16 109.3 . . ?
O7 C16 C15 111.63(11) . . ?
O7 C16 H16 109.3 . . ?
O7 C16 C17 107.61(10) . . ?
C16 C17 H17 108.0 . . ?
C16 C17 C18 111.82(11) . . ?
C18 C17 H17 108.0 . . ?
O8 C17 C16 110.06(10) . . ?
O8 C17 H17 108.0 . . ?
O8 C17 C18 110.80(11) . . ?
C17 C18 H18 109.6 . . ?
C17 C18 C19 111.04(11) . . ?
C19 C18 H18 109.6 . . ?
N2 C18 C17 106.73(10) . . ?
N2 C18 H18 109.6 . . ?
N2 C18 C19 110.37(11) . . ?
C18 C19 H19A 109.3 . . ?
C18 C19 H19B 109.3 . . ?
H19A C19 H19B 108.0 . . ?
O9 C19 C18 111.51(11) . . ?
O9 C19 H19A 109.3 . . ?
O9 C19 H19B 109.3 . . ?
H20A C20 H20B 108.7 . . ?
C21 C20 H20A 110.6 . . ?
C21 C20 H20B 110.6 . . ?
O10 C20 H20A 110.6 . . ?
O10 C20 H20B 110.6 . . ?
O10 C20 C21 105.62(12) . . ?
C22 C21 C20 119.39(9) . . ?
C22 C21 C26 120.0 . . ?
C26 C21 C20 120.59(9) . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 120.0 . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 120.0 . . ?
C24 C23 C22 120.0 . . ?
C24 C23 H23 120.0 . . ?
C23 C24 H24 120.0 . . ?
C25 C24 C23 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 H25 120.0 . . ?
C26 C25 C24 120.0 . . ?
C26 C25 H25 120.0 . . ?
C21 C26 H26 120.0 . . ?
C25 C26 C21 120.0 . . ?
C25 C26 H26 120.0 . . ?
C18 N2 C14 110.65(10) . . ?
O10 N2 C14 106.01(10) . . ?
O10 N2 C18 104.87(9) . . ?
C15 O6 H6 109.5 . . ?
C16 O7 H7 109.5 . . ?
C17 O8 H8 109.5 . . ?
C19 O9 H9B 109.5 . . ?
C20 O10 N2 109.12(10) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2A O8 0.84 1.83 2.6499(13) 163.8 2_565
O3 H3A O4 0.84 1.87 2.7132(13) 176.5 2_576
O6 H6 O7 0.84 2.06 2.8814(13) 165.8 1_655
O7 H7 O1 0.84 1.94 2.7666(13) 170.2 .
O8 H8 O9 0.84 2.01 2.7652(14) 148.7 1_655
O9 H9B O1 0.84 2.12 2.9047(14) 154.4 2_565
O4 H4A N1 0.82(2) 2.16(2) 2.9729(14) 171.5(19) 1_455

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 57.08(13) . . . . ?
C1 C2 C3 O2 -61.80(13) . . . . ?
C1 N1 O5 C7 121.05(11) . . . . ?
C2 C1 N1 C5 63.20(12) . . . . ?
C2 C1 N1 O5 175.31(9) . . . . ?
C2 C3 C4 C5 -56.11(13) . . . . ?
C2 C3 C4 O3 65.64(13) . . . . ?
C3 C4 C5 C6 -178.48(10) . . . . ?
C3 C4 C5 N1 58.70(13) . . . . ?
C4 C5 C6 O4 60.08(13) . . . . ?
C4 C5 N1 C1 -61.96(13) . . . . ?
C4 C5 N1 O5 -173.72(9) . . . . ?
C5 N1 O5 C7 -123.43(11) . . . . ?
C6 C5 N1 C1 175.04(10) . . . . ?
C6 C5 N1 O5 63.27(12) . . . . ?
C7 C8 C9 C10 -179.4(3) . . . . ?
C7 C8 C13 C12 179.4(3) . . . . ?
C7 C8A C13A C12A -173.6(3) . . . . ?
C7 C8A C9A C10A 173.7(3) . . . . ?
C8 C7 C8A C13A 106(2) . . . . ?
C8 C7 C8A C9A -68(2) . . . . ?
C8 C7 O5 N1 172.28(17) . . . . ?
C8 C9 C10 C11 0.0 . . . . ?
C9 C8 C13 C12 0.0 . . . . ?
C9 C10 C11 C12 0.0 . . . . ?
C10 C11 C12 C13 0.0 . . . . ?
C11 C12 C13 C8 0.0 . . . . ?
C13 C8 C9 C10 0.0 . . . . ?
C8A C7 C8 C9 83(2) . . . . ?
C8A C7 C8 C13 -97(2) . . . . ?
C8A C7 O5 N1 172.99(17) . . . . ?
C8A C13A C12A C11A 0.0 . . . . ?
C13A C8A C9A C10A 0.0 . . . . ?
C13A C12A C11A C10A 0.0 . . . . ?
C12A C11A C10A C9A 0.0 . . . . ?
C11A C10A C9A C8A 0.0 . . . . ?
C9A C8A C13A C12A 0.0 . . . . ?
N1 C1 C2 C3 -61.18(13) . . . . ?
N1 C1 C2 O1 179.34(9) . . . . ?
N1 C5 C6 O4 -178.31(10) . . . . ?
O1 C2 C3 C4 177.51(9) . . . . ?
O1 C2 C3 O2 58.64(13) . . . . ?
O2 C3 C4 C5 63.69(13) . . . . ?
O2 C3 C4 O3 -174.56(10) . . . . ?
O3 C4 C5 C6 62.85(13) . . . . ?
O3 C4 C5 N1 -59.97(13) . . . . ?
O5 C7 C8 C9 -103.4(3) . . . . ?
O5 C7 C8 C13 77.2(3) . . . . ?
O5 C7 C8A C13A 99.8(3) . . . . ?
O5 C7 C8A C9A -73.8(3) . . . . ?
C14 C15 C16 C17 -52.96(14) . . . . ?
C14 C15 C16 O7 66.23(13) . . . . ?
C14 N2 O10 C20 -105.72(12) . . . . ?
C15 C14 N2 C18 -65.77(13) . . . . ?
C15 C14 N2 O10 -178.93(10) . . . . ?
C15 C16 C17 C18 54.02(14) . . . . ?
C15 C16 C17 O8 -69.58(13) . . . . ?
C16 C17 C18 C19 -179.34(10) . . . . ?
C16 C17 C18 N2 -59.00(13) . . . . ?
C17 C18 C19 O9 -52.84(15) . . . . ?
C17 C18 N2 C14 65.06(13) . . . . ?
C17 C18 N2 O10 178.94(10) . . . . ?
C18 N2 O10 C20 137.16(12) . . . . ?
C19 C18 N2 C14 -174.18(11) . . . . ?
C19 C18 N2 O10 -60.29(13) . . . . ?
C20 C21 C22 C23 -178.32(12) . . . . ?
C20 C21 C26 C25 178.30(12) . . . . ?
C21 C20 O10 N2 -172.96(10) . . . . ?
C21 C22 C23 C24 0.0 . . . . ?
C22 C21 C26 C25 0.0 . . . . ?
C22 C23 C24 C25 0.0 . . . . ?
C23 C24 C25 C26 0.0 . . . . ?
C24 C25 C26 C21 0.0 . . . . ?
C26 C21 C22 C23 0.0 . . . . ?
N2 C14 C15 C16 58.47(14) . . . . ?
N2 C14 C15 O6 179.93(10) . . . . ?
N2 C18 C19 O9 -171.00(11) . . . . ?
O6 C15 C16 C17 -174.12(10) . . . . ?
O6 C15 C16 O7 -54.93(13) . . . . ?
O7 C16 C17 C18 -67.61(13) . . . . ?
O7 C16 C17 O8 168.80(10) . . . . ?
O8 C17 C18 C19 -56.16(14) . . . . ?
O8 C17 C18 N2 64.18(13) . . . . ?
O10 C20 C21 C22 72.71(14) . . . . ?
O10 C20 C21 C26 -105.59(12) . . . . ?
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
