# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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_seesen
_database_code_depnum_ccdc_archive 'CCDC 1037209'
_audit_update_record             
;
2014-12-02 deposited with the CCDC.
2015-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H11 N O'
_chemical_formula_weight         101.15

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'

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'P -4 21 c'

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

_cell_length_a                   12.0295(4)
_cell_length_b                   12.0295(4)
_cell_length_c                   8.0824(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1169.59(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3009
_cell_measurement_theta_min      2.3980
_cell_measurement_theta_max      26.7010

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Eos'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 16.1419
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9202
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_sigmaI/netI    0.0189
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.39
_diffrn_reflns_theta_max         26.73
_reflns_number_total             729
_reflns_number_gt                668
_reflns_threshold_expression     >2sigma(I)

_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    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

 The NH and OH hydrogens were refined freely. All other hydrogens were
 placed in calculated positions and refined using a riding model.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0301P)²+0.2877P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.8(19)
_refine_ls_number_reflns         729
_refine_ls_number_parameters     72
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0716
_refine_ls_wR_factor_gt          0.0696
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.29868(9) 0.75086(10) 0.03255(14) 0.0187(3) Uani 1 1 d . . .
H02 H 0.238(2) 0.7475(19) 0.090(3) 0.047(7) Uiso 1 1 d . . .
N11 N 0.61380(11) 0.74244(13) 0.26833(19) 0.0193(3) Uani 1 1 d . . .
H01 H 0.6454(17) 0.7047(16) 0.185(3) 0.029(6) Uiso 1 1 d . . .
C12 C 0.52262(15) 0.67760(16) 0.3414(2) 0.0241(4) Uani 1 1 d . . .
H12A H 0.4944 0.7172 0.4402 0.029 Uiso 1 1 calc R . .
H12B H 0.5519 0.6048 0.3782 0.029 Uiso 1 1 calc R . .
C13 C 0.42608(14) 0.65805(15) 0.2216(2) 0.0213(4) Uani 1 1 d . . .
H13A H 0.4511 0.6097 0.1297 0.026 Uiso 1 1 calc R . .
H13B H 0.3648 0.6196 0.2801 0.026 Uiso 1 1 calc R . .
C14 C 0.38421(13) 0.76773(13) 0.1523(2) 0.0155(4) Uani 1 1 d . . .
H14 H 0.3533 0.8130 0.2453 0.019 Uiso 1 1 calc R . .
C15 C 0.47913(13) 0.83151(14) 0.0735(2) 0.0185(4) Uani 1 1 d . . .
H15A H 0.4522 0.9050 0.0356 0.022 Uiso 1 1 calc R . .
H15B H 0.5068 0.7903 -0.0241 0.022 Uiso 1 1 calc R . .
C16 C 0.57367(14) 0.84741(15) 0.1975(2) 0.0203(4) Uani 1 1 d . . .
H16A H 0.6363 0.8854 0.1416 0.024 Uiso 1 1 calc R . .
H16B H 0.5477 0.8962 0.2883 0.024 Uiso 1 1 calc R . .


_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 C14 1.4272(19) . ?
N11 C16 1.468(2) . ?
N11 C12 1.470(2) . ?
C12 C13 1.530(2) . ?
C13 C14 1.519(2) . ?
C14 C15 1.516(2) . ?
C15 C16 1.528(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
C16 N11 C12 111.58(13) . . ?
N11 C12 C13 113.19(14) . . ?
C14 C13 C12 110.57(15) . . ?
O1 C14 C15 109.27(13) . . ?
O1 C14 C13 111.43(13) . . ?
C15 C14 C13 110.16(13) . . ?
C14 C15 C16 110.40(14) . . ?
N11 C16 C15 113.13(14) . . ?

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
C16 N11 C12 C13 53.5(2) . . . . ?
N11 C12 C13 C14 -54.5(2) . . . . ?
C12 C13 C14 O1 176.41(14) . . . . ?
C12 C13 C14 C15 54.96(18) . . . . ?
O1 C14 C15 C16 -178.11(13) . . . . ?
C13 C14 C15 C16 -55.38(18) . . . . ?
C12 N11 C16 C15 -53.97(18) . . . . ?
C14 C15 C16 N11 55.49(18) . . . . ?

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 H02 N11 0.86(2) 1.89(3) 2.7464(18) 172(2) 6_465
N11 H01 O1 0.90(2) 2.17(2) 2.9794(19) 150.1(18) 3_565
C14 H14 O1 1.00 2.63 3.487(2) 143.2 8_455

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.73
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.032

####################################################################### 
# 
# 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_siegen
_database_code_depnum_ccdc_archive 'CCDC 1037210'
_audit_update_record             
;
2014-12-02 deposited with the CCDC.
2015-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H11 N O'
_chemical_formula_weight         101.15

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'F d d 2'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   21.3459(7)
_cell_length_b                   18.6413(6)
_cell_length_c                   5.93539(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2361.78(13)
_cell_formula_units_Z            16
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8898
_cell_measurement_theta_min      2.8930
_cell_measurement_theta_max      30.6690

_exptl_crystal_description       'needle (cut to equidimensional block)'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.35
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.138
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Eos'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 16.1419
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20678
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_sigmaI/netI    0.0105
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.90
_diffrn_reflns_theta_max         30.83
_reflns_number_total             987
_reflns_number_gt                959
_reflns_threshold_expression     >2sigma(I)

_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    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

 The NH and OH hydrogens were refined freely. All other hydrogens were
 placed in calculated positions and refined using a riding model.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0375P)²+1.2034P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.9(12)
_refine_ls_number_reflns         987
_refine_ls_number_parameters     72
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0271
_refine_ls_wR_factor_ref         0.0694
_refine_ls_wR_factor_gt          0.0686
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.002
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.41195(4) 0.24000(4) 0.46117(15) 0.02241(19) Uani 1 1 d . . .
H02 H 0.4282(8) 0.2645(9) 0.350(4) 0.038(5) Uiso 1 1 d . . .
N11 N 0.28059(4) 0.07472(5) 0.39406(17) 0.0191(2) Uani 1 1 d . . .
H01 H 0.2456(8) 0.0537(9) 0.363(3) 0.033(4) Uiso 1 1 d . . .
C12 C 0.31059(5) 0.09918(6) 0.1852(2) 0.0225(2) Uani 1 1 d . . .
H12A H 0.2816 0.1309 0.1014 0.027 Uiso 1 1 calc R . .
H12B H 0.3204 0.0573 0.0887 0.027 Uiso 1 1 calc R . .
C13 C 0.37078(5) 0.13994(6) 0.23964(19) 0.0199(2) Uani 1 1 d . . .
H13A H 0.4008 0.1074 0.3148 0.024 Uiso 1 1 calc R . .
H13B H 0.3902 0.1573 0.0983 0.024 Uiso 1 1 calc R . .
C14 C 0.35667(4) 0.20331(5) 0.39278(18) 0.0165(2) Uani 1 1 d . . .
H14 H 0.3291 0.2377 0.3100 0.020 Uiso 1 1 calc R . .
C15 C 0.32260(5) 0.17792(6) 0.60251(19) 0.0186(2) Uani 1 1 d . . .
H15A H 0.3107 0.2198 0.6954 0.022 Uiso 1 1 calc R . .
H15B H 0.3509 0.1472 0.6932 0.022 Uiso 1 1 calc R . .
C16 C 0.26409(5) 0.13563(6) 0.5395(2) 0.0197(2) Uani 1 1 d . . .
H16A H 0.2434 0.1178 0.6780 0.024 Uiso 1 1 calc R . .
H16B H 0.2343 0.1674 0.4598 0.024 Uiso 1 1 calc R . .


_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 C14 1.4230(12) . ?
N11 C12 1.4679(15) . ?
N11 C16 1.4692(14) . ?
C12 C13 1.5272(14) . ?
C13 C14 1.5207(15) . ?
C14 C15 1.5174(15) . ?
C15 C16 1.5234(14) . ?

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
C12 N11 C16 111.15(9) . . ?
N11 C12 C13 110.05(9) . . ?
C14 C13 C12 110.27(8) . . ?
O1 C14 C15 108.26(9) . . ?
O1 C14 C13 112.31(8) . . ?
C15 C14 C13 110.05(8) . . ?
C14 C15 C16 110.67(9) . . ?
N11 C16 C15 110.34(8) . . ?

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
C16 N11 C12 C13 60.54(11) . . . . ?
N11 C12 C13 C14 -57.87(12) . . . . ?
C12 C13 C14 O1 175.84(9) . . . . ?
C12 C13 C14 C15 55.15(11) . . . . ?
O1 C14 C15 C16 -177.84(8) . . . . ?
C13 C14 C15 C16 -54.74(11) . . . . ?
C12 N11 C16 C15 -60.05(11) . . . . ?
C14 C15 C16 N11 56.94(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 H02 N11 0.87(2) 1.88(2) 2.7461(13) 171.6(18) 12_554
N11 H01 O1 0.862(17) 2.161(18) 3.0079(12) 167.1(18) 11_454
C12 H12B O1 0.99 2.60 3.5216(14) 155.7 16_544

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        30.50
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.031

####################################################################### 
# 
# 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_meppen
_database_code_depnum_ccdc_archive 'CCDC 1037211'
_audit_update_record             
;
2014-12-02 deposited with the CCDC.
2015-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H12 Cl N O'
_chemical_formula_weight         137.61

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

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

_cell_length_a                   5.3800(2)
_cell_length_b                   20.4924(11)
_cell_length_c                   6.4026(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.745(5)
_cell_angle_gamma                90.00
_cell_volume                     691.10(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5056
_cell_measurement_theta_min      3.7980
_cell_measurement_theta_max      29.9860

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             296
_exptl_absorpt_coefficient_mu    0.460
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.98302
_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)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Eos'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 16.1419
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18001
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.40
_diffrn_reflns_theta_max         30.80
_reflns_number_total             2057
_reflns_number_gt                1788
_reflns_threshold_expression     >2sigma(I)

_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    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

 The NH and OH hydrogens were refined freely. All other hydrogens were placed in
 calculated positions and refined using a riding model.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0267P)²+0.2508P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2057
_refine_ls_number_parameters     85
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0300
_refine_ls_wR_factor_ref         0.0687
_refine_ls_wR_factor_gt          0.0640
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.20466(5) 0.421291(14) 0.93127(4) 0.01753(8) Uani 1 1 d . . .
O1 O 0.38340(18) 0.31826(5) 0.62506(15) 0.0258(2) Uani 1 1 d . . .
H03 H 0.348(3) 0.3467(9) 0.707(3) 0.035(5) Uiso 1 1 d . . .
N11 N 0.76619(18) 0.39828(5) 0.18090(15) 0.01434(19) Uani 1 1 d . . .
H01 H 0.882(3) 0.4099(7) 0.109(2) 0.023(4) Uiso 1 1 d . . .
H02 H 0.614(3) 0.4083(7) 0.100(2) 0.025(4) Uiso 1 1 d . . .
C12 C 0.7976(2) 0.43377(5) 0.38784(17) 0.0150(2) Uani 1 1 d . . .
H12A H 0.7883 0.4814 0.3617 0.018 Uiso 1 1 calc R . .
H12B H 0.9659 0.4237 0.4775 0.018 Uiso 1 1 calc R . .
C13 C 0.5894(2) 0.41319(5) 0.50295(17) 0.0144(2) Uani 1 1 d . . .
H13A H 0.4221 0.4261 0.4171 0.017 Uiso 1 1 calc R . .
H13B H 0.6131 0.4359 0.6421 0.017 Uiso 1 1 calc R . .
C14 C 0.5942(2) 0.33973(5) 0.53909(18) 0.0160(2) Uani 1 1 d . . .
H14 H 0.7552 0.3277 0.6399 0.019 Uiso 1 1 calc R . .
C15 C 0.5804(2) 0.30319(6) 0.33033(19) 0.0173(2) Uani 1 1 d . . .
H15A H 0.4106 0.3098 0.2385 0.021 Uiso 1 1 calc R . .
H15B H 0.6022 0.2559 0.3603 0.021 Uiso 1 1 calc R . .
C16 C 0.7826(2) 0.32599(6) 0.21159(19) 0.0176(2) Uani 1 1 d . . .
H16A H 0.9529 0.3141 0.2940 0.021 Uiso 1 1 calc R . .
H16B H 0.7578 0.3041 0.0711 0.021 Uiso 1 1 calc R . .


_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 C14 1.4271(13) . ?
N11 C12 1.4906(14) . ?
N11 C16 1.4946(15) . ?
C12 C13 1.5206(15) . ?
C13 C14 1.5225(15) . ?
C14 C15 1.5207(15) . ?
C15 C16 1.5219(15) . ?

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
C12 N11 C16 111.95(9) . . ?
N11 C12 C13 109.51(9) . . ?
C12 C13 C14 110.89(9) . . ?
O1 C14 C15 106.67(9) . . ?
O1 C14 C13 111.92(9) . . ?
C15 C14 C13 110.92(9) . . ?
C14 C15 C16 112.08(9) . . ?
N11 C16 C15 109.93(9) . . ?

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
C16 N11 C12 C13 -60.25(11) . . . . ?
N11 C12 C13 C14 57.65(12) . . . . ?
C12 C13 C14 O1 -173.41(9) . . . . ?
C12 C13 C14 C15 -54.41(12) . . . . ?
O1 C14 C15 C16 175.02(9) . . . . ?
C13 C14 C15 C16 52.90(12) . . . . ?
C12 N11 C16 C15 58.30(12) . . . . ?
C14 C15 C16 N11 -54.19(12) . . . . ?

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 H03 Cl1 0.832(18) 2.333(18) 3.1613(10) 173.6(16) .
N11 H01 Cl1 0.880(16) 2.273(16) 3.1427(10) 169.7(14) 1_654
N11 H02 Cl1 0.900(16) 2.262(16) 3.1524(10) 170.2(13) 1_554
C12 H12A Cl1 0.99 2.74 3.6035(11) 145.6 3_666
C12 H12B Cl1 0.99 2.93 3.7236(11) 138.0 1_655
C15 H15B O1 0.99 2.79 3.3838(14) 118.9 4_665
C16 H16A O1 0.99 2.80 3.7413(16) 158.1 1_655
C16 H16B O1 0.99 2.60 3.0759(15) 109.5 4_665

_diffrn_measured_fraction_theta_max 0.947
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_vechta
_database_code_depnum_ccdc_archive 'CCDC 1037212'
_audit_update_record             
;
2014-12-02 deposited with the CCDC.
2015-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H22 N2 O2'
_chemical_formula_weight         214.31

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P c a 21'

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

_cell_length_a                   11.5417(12)
_cell_length_b                   5.0515(5)
_cell_length_c                   21.0649(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1228.13(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2364
_cell_measurement_theta_min      3.5220
_cell_measurement_theta_max      26.3850

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.159
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.96082
_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)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Eos'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 16.1419
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23143
_diffrn_reflns_av_R_equivalents  0.0867
_diffrn_reflns_av_sigmaI/netI    0.0387
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.53
_diffrn_reflns_theta_max         28.28
_reflns_number_total             1565
_reflns_number_gt                1355
_reflns_threshold_expression     >2sigma(I)

_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    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

 The OH hydrogens were refined freely but with OH distance restraints.
 All other hydrogens were placed in calculated positions and refined
 using a riding model.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0384P)²+0.1244P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.2(15)
_refine_ls_number_reflns         1565
_refine_ls_number_parameters     144
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.0877
_refine_ls_wR_factor_gt          0.0825
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.043
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.35941(14) 0.6740(3) 0.52324(7) 0.0209(4) Uani 1 1 d D . .
H01 H 0.388(3) 0.528(6) 0.5381(15) 0.050(10) Uiso 1 1 d D . .
O2 O 0.56609(15) 0.8244(3) 0.05953(8) 0.0256(4) Uani 1 1 d D . .
H02 H 0.595(3) 0.974(6) 0.0486(18) 0.066(11) Uiso 1 1 d D . .
N11 N 0.29875(16) 0.7516(4) 0.32780(8) 0.0164(4) Uani 1 1 d . . .
N21 N 0.34981(15) 0.7084(4) 0.21739(8) 0.0167(4) Uani 1 1 d . . .
C12 C 0.3629(2) 0.5165(5) 0.34786(10) 0.0201(5) Uani 1 1 d . . .
H12A H 0.4275 0.4834 0.3180 0.024 Uiso 1 1 calc R . .
H12B H 0.3109 0.3605 0.3471 0.024 Uiso 1 1 calc R . .
C13 C 0.4107(2) 0.5541(5) 0.41462(10) 0.0192(5) Uani 1 1 d . . .
H13A H 0.4514 0.3909 0.4281 0.023 Uiso 1 1 calc R . .
H13B H 0.4676 0.7008 0.4145 0.023 Uiso 1 1 calc R . .
C14 C 0.31471(19) 0.6159(4) 0.46123(9) 0.0160(5) Uani 1 1 d . . .
H14 H 0.2622 0.4590 0.4643 0.019 Uiso 1 1 calc R . .
C15 C 0.2451(2) 0.8514(4) 0.43815(10) 0.0193(5) Uani 1 1 d . . .
H15A H 0.2942 1.0122 0.4390 0.023 Uiso 1 1 calc R . .
H15B H 0.1783 0.8809 0.4668 0.023 Uiso 1 1 calc R . .
C16 C 0.2019(2) 0.8033(5) 0.37090(11) 0.0206(5) Uani 1 1 d . . .
H16A H 0.1484 0.6500 0.3707 0.025 Uiso 1 1 calc R . .
H16B H 0.1584 0.9604 0.3560 0.025 Uiso 1 1 calc R . .
C22 C 0.3033(2) 0.6475(5) 0.15406(10) 0.0195(5) Uani 1 1 d . . .
H22A H 0.2514 0.7924 0.1402 0.023 Uiso 1 1 calc R . .
H22B H 0.2573 0.4824 0.1560 0.023 Uiso 1 1 calc R . .
C23 C 0.4011(2) 0.6148(4) 0.10634(11) 0.0188(5) Uani 1 1 d . . .
H23A H 0.4516 0.4659 0.1194 0.023 Uiso 1 1 calc R . .
H23B H 0.3685 0.5729 0.0640 0.023 Uiso 1 1 calc R . .
C24 C 0.47164(19) 0.8659(4) 0.10247(10) 0.0180(5) Uani 1 1 d . . .
H24 H 0.4215 1.0117 0.0858 0.022 Uiso 1 1 calc R . .
C25 C 0.51405(19) 0.9399(4) 0.16877(9) 0.0186(5) Uani 1 1 d . . .
H25A H 0.5703 0.8053 0.1836 0.022 Uiso 1 1 calc R . .
H25B H 0.5545 1.1125 0.1669 0.022 Uiso 1 1 calc R . .
C26 C 0.41495(19) 0.9577(4) 0.21575(10) 0.0189(5) Uani 1 1 d . . .
H26A H 0.4459 0.9967 0.2586 0.023 Uiso 1 1 calc R . .
H26B H 0.3626 1.1041 0.2034 0.023 Uiso 1 1 calc R . .
C1 C 0.2554(2) 0.7240(5) 0.26322(10) 0.0206(5) Uani 1 1 d . . .
H1A H 0.2055 0.8774 0.2529 0.025 Uiso 1 1 calc R . .
H1B H 0.2074 0.5619 0.2602 0.025 Uiso 1 1 calc R . .


_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 C14 1.435(2) . ?
O2 C24 1.432(3) . ?
N11 C1 1.456(3) . ?
N11 C12 1.462(3) . ?
N11 C16 1.464(3) . ?
N21 C1 1.458(3) . ?
N21 C26 1.467(3) . ?
N21 C22 1.470(3) . ?
C12 C13 1.523(3) . ?
C13 C14 1.513(3) . ?
C14 C15 1.516(3) . ?
C15 C16 1.521(3) . ?
C22 C23 1.521(3) . ?
C23 C24 1.509(3) . ?
C24 C25 1.526(3) . ?
C25 C26 1.515(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
C1 N11 C12 111.49(17) . . ?
C1 N11 C16 109.50(17) . . ?
C12 N11 C16 110.63(17) . . ?
C1 N21 C26 110.65(16) . . ?
C1 N21 C22 109.82(17) . . ?
C26 N21 C22 110.19(16) . . ?
N11 C12 C13 110.44(18) . . ?
C14 C13 C12 111.05(18) . . ?
O1 C14 C13 111.69(17) . . ?
O1 C14 C15 108.79(17) . . ?
C13 C14 C15 109.99(17) . . ?
C14 C15 C16 110.32(17) . . ?
N11 C16 C15 110.81(18) . . ?
N21 C22 C23 110.59(18) . . ?
C24 C23 C22 110.14(18) . . ?
O2 C24 C23 108.76(17) . . ?
O2 C24 C25 111.70(18) . . ?
C23 C24 C25 109.23(17) . . ?
C26 C25 C24 111.72(18) . . ?
N21 C26 C25 110.57(17) . . ?
N11 C1 N21 111.50(18) . . ?

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 N11 C12 C13 178.08(18) . . . . ?
C16 N11 C12 C13 -59.8(2) . . . . ?
N11 C12 C13 C14 57.0(2) . . . . ?
C12 C13 C14 O1 -175.08(18) . . . . ?
C12 C13 C14 C15 -54.2(2) . . . . ?
O1 C14 C15 C16 176.84(18) . . . . ?
C13 C14 C15 C16 54.2(2) . . . . ?
C1 N11 C16 C15 -176.23(17) . . . . ?
C12 N11 C16 C15 60.5(2) . . . . ?
C14 C15 C16 N11 -57.6(2) . . . . ?
C1 N21 C22 C23 -176.72(18) . . . . ?
C26 N21 C22 C23 61.1(2) . . . . ?
N21 C22 C23 C24 -59.6(2) . . . . ?
C22 C23 C24 O2 177.27(18) . . . . ?
C22 C23 C24 C25 55.1(2) . . . . ?
O2 C24 C25 C26 -174.46(18) . . . . ?
C23 C24 C25 C26 -54.1(2) . . . . ?
C1 N21 C26 C25 179.22(18) . . . . ?
C22 N21 C26 C25 -59.1(2) . . . . ?
C24 C25 C26 N21 56.3(2) . . . . ?
C12 N11 C1 N21 -65.1(2) . . . . ?
C16 N11 C1 N21 172.18(19) . . . . ?
C26 N21 C1 N11 -65.2(2) . . . . ?
C22 N21 C1 N11 172.98(17) . . . . ?

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 H01 O2 0.86(3) 1.91(3) 2.768(2) 170(3) 2_665
O2 H02 O1 0.85(3) 1.93(3) 2.783(2) 173(3) 2_674
C26 H26A N11 0.99 2.56 2.907(3) 100.6 .
C12 H12A N21 0.99 2.57 2.918(3) 100.8 .

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_regen_twin1_hklf5
_database_code_depnum_ccdc_archive 'CCDC 1037213'
_audit_update_record             
;
2014-12-02 deposited with the CCDC.
2015-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H22 N2 O4'
_chemical_formula_weight         246.31

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.4947(10)
_cell_length_b                   11.9000(11)
_cell_length_c                   16.836(2)
_cell_angle_alpha                76.943(10)
_cell_angle_beta                 81.326(10)
_cell_angle_gamma                68.873(9)
_cell_volume                     1905.0(4)
_cell_formula_units_Z            6
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4770
_cell_measurement_theta_min      2.4880
_cell_measurement_theta_max      22.9450

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             804
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.98533
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;

_exptl_special_details           
;
 The crystal was a non-merohedral twin (by 180 degree rotation about
 the c* axis).
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford diffraction Xcalibur, Eos'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 16.1419
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10054
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1327
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         25.68
_reflns_number_total             10054
_reflns_number_gt                5922
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

 The structure was refined using the "HKLF 5" method. The scale factor
 refined to 0.4150(7).The detwinning routines merge equivalent reflections,
 so that R(int) is meaningless. The intensity dataset comprised all
 non-overlapped reflections from the major component and all overlapped
 reflections, so that the number of reflections should be interpreted
 with caution.

 All NH hydrogens were refined freely. The N-H distances were refined using
 restraints (SADI). All OH hydrogens were refined using a riding model
 (AFIX 147).
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0494P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         10054
_refine_ls_number_parameters     491
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.1017
_refine_ls_R_factor_gt           0.0540
_refine_ls_wR_factor_ref         0.1144
_refine_ls_wR_factor_gt          0.1059
_refine_ls_goodness_of_fit_ref   0.905
_refine_ls_restrained_S_all      0.905
_refine_ls_shift/su_max          0.005
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N11 N -0.4942(3) 0.2918(2) 0.91989(15) 0.0154(6) Uani 1 1 d D . .
H01 H -0.565(2) 0.279(3) 0.9025(16) 0.026(9) Uiso 1 1 d D . .
H02 H -0.444(2) 0.322(2) 0.8750(12) 0.006(7) Uiso 1 1 d D . .
C12 C -0.4062(3) 0.1759(3) 0.96723(18) 0.0179(8) Uani 1 1 d . . .
H12A H -0.3235 0.1876 0.9801 0.021 Uiso 1 1 calc R . .
H12B H -0.3764 0.1110 0.9338 0.021 Uiso 1 1 calc R . .
C13 C -0.4828(3) 0.1355(3) 1.04627(17) 0.0211(8) Uani 1 1 d . . .
H13A H -0.5586 0.1134 1.0331 0.025 Uiso 1 1 calc R . .
H13B H -0.4197 0.0615 1.0785 0.025 Uiso 1 1 calc R . .
C14 C -0.5403(3) 0.2345(3) 1.09685(18) 0.0187(8) Uani 1 1 d . . .
H14 H -0.5962 0.2070 1.1457 0.022 Uiso 1 1 calc R . .
C15 C -0.6303(3) 0.3523(3) 1.04659(17) 0.0172(7) Uani 1 1 d . . .
H15A H -0.7117 0.3393 1.0326 0.021 Uiso 1 1 calc R . .
H15B H -0.6624 0.4184 1.0791 0.021 Uiso 1 1 calc R . .
C16 C -0.5506(3) 0.3896(3) 0.96944(17) 0.0174(7) Uani 1 1 d . . .
H16A H -0.6113 0.4643 0.9364 0.021 Uiso 1 1 calc R . .
H16B H -0.4744 0.4099 0.9838 0.021 Uiso 1 1 calc R . .
O1 O -0.42689(18) 0.25418(19) 1.12344(12) 0.0201(5) Uani 1 1 d . . .
H07 H -0.4569 0.3107 1.1507 0.024 Uiso 1 1 calc R . .
N21 N 0.2863(3) 0.5288(2) 0.74611(15) 0.0184(7) Uani 1 1 d D . .
H03 H 0.366(2) 0.521(3) 0.7678(17) 0.040(11) Uiso 1 1 d D . .
H04 H 0.235(2) 0.498(2) 0.7911(12) 0.015(8) Uiso 1 1 d D . .
C22 C 0.3226(3) 0.4599(3) 0.67870(18) 0.0283(9) Uani 1 1 d . . .
H22A H 0.2379 0.4607 0.6590 0.034 Uiso 1 1 calc R . .
H22B H 0.3777 0.3735 0.6990 0.034 Uiso 1 1 calc R . .
C23 C 0.4034(3) 0.5148(3) 0.60863(18) 0.0241(8) Uani 1 1 d . . .
H23A H 0.4925 0.5061 0.6267 0.029 Uiso 1 1 calc R . .
H23B H 0.4217 0.4699 0.5629 0.029 Uiso 1 1 calc R . .
C24 C 0.3251(3) 0.6485(3) 0.57961(18) 0.0241(8) Uani 1 1 d . . .
H24 H 0.2402 0.6562 0.5555 0.029 Uiso 1 1 calc R . .
C25 C 0.2862(3) 0.7168(3) 0.64972(17) 0.0213(8) Uani 1 1 d . . .
H25A H 0.2307 0.8033 0.6303 0.026 Uiso 1 1 calc R . .
H25B H 0.3702 0.7156 0.6705 0.026 Uiso 1 1 calc R . .
C26 C 0.2050(3) 0.6594(3) 0.71833(17) 0.0201(8) Uani 1 1 d . . .
H26A H 0.1830 0.7037 0.7645 0.024 Uiso 1 1 calc R . .
H26B H 0.1178 0.6655 0.6989 0.024 Uiso 1 1 calc R . .
O2 O 0.4108(2) 0.69986(19) 0.51760(13) 0.0307(6) Uani 1 1 d . . .
H08 H 0.3840 0.7762 0.5145 0.037 Uiso 1 1 calc R . .
N31 N 0.8820(3) 0.0748(2) 0.60203(16) 0.0178(6) Uani 1 1 d D . .
H05 H 0.823(3) 0.069(3) 0.5684(15) 0.029(10) Uiso 1 1 d D . .
H06 H 0.940(3) 0.106(3) 0.5630(19) 0.091(16) Uiso 1 1 d D . .
C32 C 0.8062(3) 0.1836(3) 0.63961(18) 0.0207(8) Uani 1 1 d . . .
H32A H 0.7694 0.2557 0.5963 0.025 Uiso 1 1 calc R . .
H32B H 0.8692 0.2012 0.6694 0.025 Uiso 1 1 calc R . .
C33 C 0.6898(3) 0.1614(3) 0.69803(18) 0.0240(8) Uani 1 1 d . . .
H33A H 0.6222 0.1518 0.6673 0.029 Uiso 1 1 calc R . .
H33B H 0.6431 0.2329 0.7252 0.029 Uiso 1 1 calc R . .
C34 C 0.7437(3) 0.0473(3) 0.76168(18) 0.0249(8) Uani 1 1 d . . .
H34 H 0.8103 0.0602 0.7923 0.030 Uiso 1 1 calc R . .
C35 C 0.8197(3) -0.0613(3) 0.72084(18) 0.0267(9) Uani 1 1 d . . .
H35A H 0.7556 -0.0766 0.6905 0.032 Uiso 1 1 calc R . .
H35B H 0.8564 -0.1351 0.7630 0.032 Uiso 1 1 calc R . .
C36 C 0.9359(3) -0.0389(3) 0.66260(18) 0.0218(8) Uani 1 1 d . . .
H36A H 1.0046 -0.0310 0.6934 0.026 Uiso 1 1 calc R . .
H36B H 0.9814 -0.1091 0.6341 0.026 Uiso 1 1 calc R . .
O3 O 0.6392(2) 0.0202(2) 0.81962(12) 0.0388(7) Uani 1 1 d . . .
H09 H 0.5658 0.0436 0.7968 0.047 Uiso 1 1 calc R . .
N41 N 0.0800(2) 0.2787(2) 0.93601(15) 0.0212(7) Uani 1 1 d . . .
C42 C 0.1203(3) 0.1465(3) 0.96288(18) 0.0228(8) Uani 1 1 d . . .
H42A H 0.2215 0.1100 0.9584 0.027 Uiso 1 1 calc R . .
H42B H 0.0841 0.1116 0.9269 0.027 Uiso 1 1 calc R . .
C43 C 0.0663(3) 0.1140(3) 1.05056(17) 0.0196(8) Uani 1 1 d . . .
H43A H 0.0899 0.0239 1.0662 0.024 Uiso 1 1 calc R . .
H43B H 0.1103 0.1408 1.0873 0.024 Uiso 1 1 calc R . .
C44 C -0.0871(3) 0.1749(3) 1.06053(18) 0.0194(8) Uani 1 1 d . . .
H44 H -0.1298 0.1456 1.0237 0.023 Uiso 1 1 calc R . .
C45 C -0.1214(3) 0.3118(3) 1.0338(2) 0.0293(9) Uani 1 1 d . . .
H45A H -0.0816 0.3424 1.0706 0.035 Uiso 1 1 calc R . .
H45B H -0.2221 0.3522 1.0387 0.035 Uiso 1 1 calc R . .
C46 C -0.0668(3) 0.3459(3) 0.9460(2) 0.0314(9) Uani 1 1 d . . .
H46A H -0.1156 0.3258 0.9082 0.038 Uiso 1 1 calc R . .
H46B H -0.0834 0.4352 0.9324 0.038 Uiso 1 1 calc R . .
O4 O -0.1363(2) 0.1409(2) 1.14200(12) 0.0305(6) Uani 1 1 d . . .
H010 H -0.2218 0.1600 1.1445 0.037 Uiso 1 1 calc R . .
C47 C 0.1649(3) 0.3330(3) 0.88621(18) 0.0193(8) Uani 1 1 d . . .
O41 O 0.2882(2) 0.26369(19) 0.86941(12) 0.0212(5) Uani 1 1 d . . .
O42 O 0.1215(2) 0.4459(2) 0.86045(13) 0.0307(6) Uani 1 1 d . . .
N51 N 0.7303(2) 0.5359(2) 0.74309(15) 0.0216(7) Uani 1 1 d . . .
C52 C 0.8702(3) 0.4648(3) 0.72173(19) 0.0257(8) Uani 1 1 d . . .
H52A H 0.8876 0.3776 0.7472 0.031 Uiso 1 1 calc R . .
H52B H 0.9331 0.4936 0.7435 0.031 Uiso 1 1 calc R . .
C53 C 0.8988(3) 0.4760(3) 0.6304(2) 0.0315(9) Uani 1 1 d . . .
H53A H 0.8466 0.4350 0.6101 0.038 Uiso 1 1 calc R . .
H53B H 0.9975 0.4331 0.6177 0.038 Uiso 1 1 calc R . .
C54 C 0.8608(3) 0.6078(3) 0.58614(19) 0.0270(9) Uani 1 1 d . . .
H54 H 0.8660 0.6094 0.5261 0.032 Uiso 1 1 calc R . .
C55 C 0.7168(3) 0.6814(3) 0.61313(19) 0.0289(9) Uani 1 1 d . . .
H55A H 0.6509 0.6550 0.5923 0.035 Uiso 1 1 calc R . .
H55B H 0.6990 0.7693 0.5895 0.035 Uiso 1 1 calc R . .
C56 C 0.6951(3) 0.6651(3) 0.7052(2) 0.0334(9) Uani 1 1 d . . .
H56A H 0.7525 0.7013 0.7255 0.040 Uiso 1 1 calc R . .
H56B H 0.5981 0.7091 0.7211 0.040 Uiso 1 1 calc R . .
O5 O 0.9579(2) 0.65713(19) 0.60112(13) 0.0270(6) Uani 1 1 d . . .
H011 H 0.9479 0.7249 0.5696 0.032 Uiso 1 1 calc R . .
C57 C 0.6351(3) 0.4828(3) 0.78226(17) 0.0165(8) Uani 1 1 d . . .
O51 O 0.6737(2) 0.36957(19) 0.80351(13) 0.0239(5) Uani 1 1 d . . .
O52 O 0.5118(2) 0.55520(19) 0.79534(12) 0.0205(5) Uani 1 1 d . . .
N61 N 0.7292(3) -0.0775(2) 0.41924(14) 0.0200(6) Uani 1 1 d . . .
C62 C 0.8018(3) -0.1831(3) 0.38056(18) 0.0245(8) Uani 1 1 d . . .
H62A H 0.7486 -0.2396 0.3922 0.029 Uiso 1 1 calc R . .
H62B H 0.8918 -0.2277 0.4036 0.029 Uiso 1 1 calc R . .
C63 C 0.8229(3) -0.1439(3) 0.28963(18) 0.0259(8) Uani 1 1 d . . .
H63A H 0.8884 -0.0986 0.2783 0.031 Uiso 1 1 calc R . .
H63B H 0.8642 -0.2178 0.2644 0.031 Uiso 1 1 calc R . .
C64 C 0.6932(3) -0.0643(3) 0.2504(2) 0.0307(9) Uani 1 1 d . . .
H64 H 0.7169 -0.0264 0.1934 0.037 Uiso 1 1 calc R . .
C65 C 0.6101(3) 0.0371(3) 0.29768(18) 0.0280(9) Uani 1 1 d . . .
H65A H 0.6544 0.1003 0.2866 0.034 Uiso 1 1 calc R . .
H65B H 0.5176 0.0762 0.2772 0.034 Uiso 1 1 calc R . .
C66 C 0.5953(3) -0.0063(3) 0.38915(18) 0.0216(8) Uani 1 1 d . . .
H66A H 0.5518 0.0652 0.4166 0.026 Uiso 1 1 calc R . .
H66B H 0.5357 -0.0574 0.4019 0.026 Uiso 1 1 calc R . .
O6 O 0.6100(2) -0.1312(2) 0.24756(15) 0.0396(7) Uani 1 1 d . . .
H012 H 0.6397 -0.1700 0.2089 0.047 Uiso 1 1 calc R . .
C67 C 0.7833(3) -0.0482(3) 0.47716(17) 0.0142(7) Uani 1 1 d U . .
O61 O 0.90380(19) -0.11639(18) 0.49708(11) 0.0168(5) Uani 1 1 d . . .
O62 O 0.71307(19) 0.04488(18) 0.50780(12) 0.0208(5) 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
N11 C16 1.481(4) . ?
N11 C12 1.482(4) . ?
C12 C13 1.521(4) . ?
C13 C14 1.504(4) . ?
C14 O1 1.442(3) . ?
C14 C15 1.525(4) . ?
C15 C16 1.504(4) . ?
N21 C22 1.473(4) . ?
N21 C26 1.483(4) . ?
C22 C23 1.512(4) . ?
C23 C24 1.508(4) . ?
C24 O2 1.448(3) . ?
C24 C25 1.507(4) . ?
C25 C26 1.514(4) . ?
N31 C32 1.478(4) . ?
N31 C36 1.480(4) . ?
C32 C33 1.511(4) . ?
C33 C34 1.512(4) . ?
C34 O3 1.431(3) . ?
C34 C35 1.507(4) . ?
C35 C36 1.509(4) . ?
N41 C47 1.363(4) . ?
N41 C42 1.455(4) . ?
N41 C46 1.462(4) . ?
C42 C43 1.516(4) . ?
C43 C44 1.509(4) . ?
C44 O4 1.413(3) . ?
C44 C45 1.511(4) . ?
C45 C46 1.523(4) . ?
C47 O42 1.248(3) . ?
C47 O41 1.289(3) . ?
N51 C57 1.379(3) . ?
N51 C52 1.444(4) . ?
N51 C56 1.458(4) . ?
C52 C53 1.506(4) . ?
C53 C54 1.512(4) . ?
C54 O5 1.422(3) . ?
C54 C55 1.509(4) . ?
C55 C56 1.511(4) . ?
C57 O51 1.240(3) . ?
C57 O52 1.289(3) . ?
N61 C67 1.363(3) . ?
N61 C66 1.453(4) . ?
N61 C62 1.454(4) . ?
C62 C63 1.503(4) . ?
C63 C64 1.497(4) . ?
C64 O6 1.389(3) . ?
C64 C65 1.522(4) . ?
C65 C66 1.513(4) . ?
C67 O62 1.262(3) . ?
C67 O61 1.279(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
C16 N11 C12 111.7(2) . . ?
N11 C12 C13 111.0(2) . . ?
C14 C13 C12 111.9(2) . . ?
O1 C14 C13 108.0(2) . . ?
O1 C14 C15 110.5(2) . . ?
C13 C14 C15 110.3(2) . . ?
C16 C15 C14 110.0(2) . . ?
N11 C16 C15 112.2(2) . . ?
C22 N21 C26 111.4(2) . . ?
N21 C22 C23 111.2(2) . . ?
C24 C23 C22 110.5(3) . . ?
O2 C24 C25 109.6(2) . . ?
O2 C24 C23 108.7(2) . . ?
C25 C24 C23 110.5(2) . . ?
C24 C25 C26 110.9(3) . . ?
N21 C26 C25 109.6(2) . . ?
C32 N31 C36 113.4(2) . . ?
N31 C32 C33 110.3(2) . . ?
C32 C33 C34 110.1(3) . . ?
O3 C34 C35 109.4(3) . . ?
O3 C34 C33 113.5(3) . . ?
C35 C34 C33 110.1(3) . . ?
C34 C35 C36 110.9(3) . . ?
N31 C36 C35 109.5(2) . . ?
C47 N41 C42 122.1(3) . . ?
C47 N41 C46 120.4(3) . . ?
C42 N41 C46 115.3(2) . . ?
N41 C42 C43 111.0(2) . . ?
C44 C43 C42 110.8(2) . . ?
O4 C44 C43 110.1(2) . . ?
O4 C44 C45 113.0(3) . . ?
C43 C44 C45 108.7(2) . . ?
C44 C45 C46 111.9(3) . . ?
N41 C46 C45 110.0(3) . . ?
O42 C47 O41 123.3(3) . . ?
O42 C47 N41 119.3(3) . . ?
O41 C47 N41 117.3(3) . . ?
C57 N51 C52 122.6(3) . . ?
C57 N51 C56 123.7(3) . . ?
C52 N51 C56 112.7(2) . . ?
N51 C52 C53 111.2(3) . . ?
C52 C53 C54 112.7(3) . . ?
O5 C54 C55 111.5(3) . . ?
O5 C54 C53 108.4(3) . . ?
C55 C54 C53 110.9(3) . . ?
C54 C55 C56 111.3(3) . . ?
N51 C56 C55 111.3(3) . . ?
O51 C57 O52 124.5(3) . . ?
O51 C57 N51 118.3(3) . . ?
O52 C57 N51 117.2(3) . . ?
C67 N61 C66 123.8(3) . . ?
C67 N61 C62 122.8(3) . . ?
C66 N61 C62 113.3(2) . . ?
N61 C62 C63 110.7(3) . . ?
C64 C63 C62 113.4(3) . . ?
O6 C64 C63 111.6(3) . . ?
O6 C64 C65 107.1(3) . . ?
C63 C64 C65 111.3(3) . . ?
C66 C65 C64 114.0(3) . . ?
N61 C66 C65 109.8(2) . . ?
O62 C67 O61 123.3(3) . . ?
O62 C67 N61 118.7(3) . . ?
O61 C67 N61 118.0(3) . . ?

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
C16 N11 C12 C13 54.7(3) . . . . ?
N11 C12 C13 C14 -54.7(3) . . . . ?
C12 C13 C14 O1 -65.8(3) . . . . ?
C12 C13 C14 C15 55.1(3) . . . . ?
O1 C14 C15 C16 63.9(3) . . . . ?
C13 C14 C15 C16 -55.4(3) . . . . ?
C12 N11 C16 C15 -56.7(3) . . . . ?
C14 C15 C16 N11 56.6(3) . . . . ?
C26 N21 C22 C23 58.3(3) . . . . ?
N21 C22 C23 C24 -55.9(4) . . . . ?
C22 C23 C24 O2 175.0(2) . . . . ?
C22 C23 C24 C25 54.7(3) . . . . ?
O2 C24 C25 C26 -175.9(2) . . . . ?
C23 C24 C25 C26 -56.2(3) . . . . ?
C22 N21 C26 C25 -58.7(3) . . . . ?
C24 C25 C26 N21 57.6(3) . . . . ?
C36 N31 C32 C33 -56.8(3) . . . . ?
N31 C32 C33 C34 56.0(3) . . . . ?
C32 C33 C34 O3 179.8(2) . . . . ?
C32 C33 C34 C35 -57.2(3) . . . . ?
O3 C34 C35 C36 -176.9(2) . . . . ?
C33 C34 C35 C36 57.8(3) . . . . ?
C32 N31 C36 C35 56.5(3) . . . . ?
C34 C35 C36 N31 -56.4(3) . . . . ?
C47 N41 C42 C43 142.5(3) . . . . ?
C46 N41 C42 C43 -54.0(3) . . . . ?
N41 C42 C43 C44 55.6(3) . . . . ?
C42 C43 C44 O4 178.4(2) . . . . ?
C42 C43 C44 C45 -57.4(3) . . . . ?
O4 C44 C45 C46 179.8(2) . . . . ?
C43 C44 C45 C46 57.3(3) . . . . ?
C47 N41 C46 C45 -143.5(3) . . . . ?
C42 N41 C46 C45 52.7(4) . . . . ?
C44 C45 C46 N41 -54.0(4) . . . . ?
C42 N41 C47 O42 175.0(3) . . . . ?
C46 N41 C47 O42 12.3(4) . . . . ?
C42 N41 C47 O41 -6.3(4) . . . . ?
C46 N41 C47 O41 -168.9(3) . . . . ?
C57 N51 C52 C53 111.9(3) . . . . ?
C56 N51 C52 C53 -56.8(3) . . . . ?
N51 C52 C53 C54 53.2(4) . . . . ?
C52 C53 C54 O5 72.2(3) . . . . ?
C52 C53 C54 C55 -50.5(4) . . . . ?
O5 C54 C55 C56 -70.0(3) . . . . ?
C53 C54 C55 C56 50.9(4) . . . . ?
C57 N51 C56 C55 -110.6(3) . . . . ?
C52 N51 C56 C55 58.1(3) . . . . ?
C54 C55 C56 N51 -54.7(3) . . . . ?
C52 N51 C57 O51 3.7(4) . . . . ?
C56 N51 C57 O51 171.3(3) . . . . ?
C52 N51 C57 O52 -177.3(3) . . . . ?
C56 N51 C57 O52 -9.7(4) . . . . ?
C67 N61 C62 C63 -120.0(3) . . . . ?
C66 N61 C62 C63 59.2(3) . . . . ?
N61 C62 C63 C64 -53.1(4) . . . . ?
C62 C63 C64 O6 -72.5(3) . . . . ?
C62 C63 C64 C65 47.0(4) . . . . ?
O6 C64 C65 C66 75.5(3) . . . . ?
C63 C64 C65 C66 -46.6(4) . . . . ?
C67 N61 C66 C65 121.2(3) . . . . ?
C62 N61 C66 C65 -58.0(3) . . . . ?
C64 C65 C66 N61 51.4(4) . . . . ?
C66 N61 C67 O62 1.1(4) . . . . ?
C62 N61 C67 O62 -179.8(3) . . . . ?
C66 N61 C67 O61 -178.2(2) . . . . ?
C62 N61 C67 O61 0.9(4) . . . . ?

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
N11 H01 O41 0.915(15) 1.791(16) 2.705(3) 176(3) 1_455
N11 H02 O51 0.935(15) 1.743(16) 2.667(3) 169(2) 1_455
N11 H02 O52 0.935(15) 2.70(2) 3.370(3) 129.5(19) 1_455
N21 H03 O52 0.929(16) 1.865(18) 2.763(3) 162(3) .
N21 H04 O41 0.942(15) 2.70(2) 3.357(3) 128(2) .
N21 H04 O42 0.942(15) 1.721(16) 2.652(3) 170(2) .
N31 H05 O62 0.931(16) 1.783(16) 2.711(3) 175(3) .
N31 H05 O61 0.931(16) 2.57(3) 3.110(3) 118(2) .
N31 H06 O61 0.936(17) 1.82(2) 2.716(3) 160(4) 2_756
O1 H07 O52 0.84 1.88 2.718(3) 174.0 2_567
O2 H08 O62 0.84 1.98 2.799(3) 166.3 2_666
O3 H09 O6 0.84 1.93 2.755(3) 167.2 2_656
O4 H010 O1 0.84 2.08 2.890(3) 161.8 .
O5 H011 O61 0.84 1.94 2.778(3) 173.7 1_565
O6 H012 O41 0.84 1.82 2.657(3) 175.6 2_656
C12 H12B O3 0.99 2.37 3.304(4) 157.7 1_455
C16 H16A O52 0.99 2.72 3.263(3) 114.9 1_455
C22 H22B O6 0.99 2.78 3.663(4) 148.6 2_656
C25 H25B O52 0.99 2.71 3.414(4) 128.1 .
C25 H25A O62 0.99 2.73 3.419(3) 126.8 2_666
C26 H26A O4 0.99 2.56 3.532(4) 166.5 2_567
C26 H26B O5 0.99 2.56 3.498(4) 157.6 1_455
C32 H32A O2 0.99 2.73 3.464(4) 131.3 2_666
C33 H33A O6 0.99 2.70 3.266(3) 116.9 2_656
C33 H33B O51 0.99 2.44 3.303(4) 145.2 .
C36 H36B O61 0.99 2.59 3.225(4) 122.0 .

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.68
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.519
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.052


#=============================================================================
# end of cif data for regen (compound 4)
#=============================================================================

#=============================================================================
# end of combined cif file
#=============================================================================
