# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# 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_akd013
_database_code_depnum_ccdc_archive 'CCDC 1501293'
_audit_update_record             
;
2016-08-29 deposited with the CCDC.	2019-02-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H23 N O4'
_chemical_formula_weight         257.32

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           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   11.6825(7)
_cell_length_b                   11.2969(5)
_cell_length_c                   11.8091(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.399(7)
_cell_angle_gamma                90.00
_cell_volume                     1460.78(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2469
_cell_measurement_theta_min      3.4980
_cell_measurement_theta_max      24.5260

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.170
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_min  0.9722
_exptl_absorpt_correction_T_max  0.9822
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Micro-Focus (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10187
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_av_sigmaI/netI    0.0456
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.50
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2567
_reflns_number_gt                1693
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_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.
;

_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)+(0.0774P)²+0.6546P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.006(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2567
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0629
_refine_ls_wR_factor_ref         0.1902
_refine_ls_wR_factor_gt          0.1637
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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 0.21150(16) 0.16659(18) 0.3566(2) 0.0657(7) Uani 1 1 d . . .
O2 O 0.25387(19) 0.3209(2) 0.2575(2) 0.0807(8) Uani 1 1 d . . .
O3 O 0.57312(19) -0.04987(19) 0.4026(2) 0.0691(7) Uani 1 1 d . . .
O4 O 0.72672(17) 0.01980(18) 0.3534(2) 0.0660(7) Uani 1 1 d . . .
H4 H 0.7164 -0.0423 0.3152 0.099 Uiso 1 1 calc R . .
N1 N 0.3968(2) 0.1859(2) 0.3516(3) 0.0667(8) Uani 1 1 d . . .
H1 H 0.4132 0.1282 0.4023 0.080 Uiso 1 1 calc R . .
C1 C 0.0851(4) 0.3176(4) 0.4003(5) 0.1082(15) Uani 1 1 d . . .
H1A H 0.1423 0.3137 0.4815 0.162 Uiso 1 1 calc R . .
H1B H 0.0048 0.3326 0.4020 0.162 Uiso 1 1 calc R . .
H1C H 0.1079 0.3803 0.3576 0.162 Uiso 1 1 calc R . .
C2 C 0.0115(3) 0.2067(5) 0.2059(4) 0.1084(16) Uani 1 1 d . . .
H2A H 0.0354 0.2745 0.1704 0.163 Uiso 1 1 calc R . .
H2B H -0.0735 0.2126 0.1954 0.163 Uiso 1 1 calc R . .
H2C H 0.0253 0.1361 0.1674 0.163 Uiso 1 1 calc R . .
C3 C 0.0407(3) 0.1030(4) 0.3984(4) 0.0941(14) Uani 1 1 d . . .
H3A H 0.0503 0.0286 0.3636 0.141 Uiso 1 1 calc R . .
H3B H -0.0440 0.1153 0.3868 0.141 Uiso 1 1 calc R . .
H3C H 0.0876 0.1026 0.4833 0.141 Uiso 1 1 calc R . .
C4 C 0.0853(2) 0.2021(3) 0.3375(3) 0.0567(8) Uani 1 1 d . . .
C5 C 0.2853(2) 0.2319(3) 0.3170(3) 0.0530(7) Uani 1 1 d . . .
C6 C 0.4931(2) 0.2267(3) 0.3093(3) 0.0561(8) Uani 1 1 d . . .
H6A H 0.4667 0.2995 0.2642 0.067 Uiso 1 1 calc R . .
H6B H 0.5049 0.1681 0.2543 0.067 Uiso 1 1 calc R . .
C7 C 0.6159(2) 0.2490(2) 0.4104(3) 0.0503(7) Uani 1 1 d . . .
C8 C 0.6077(3) 0.3510(3) 0.4935(4) 0.0733(10) Uani 1 1 d . . .
H8A H 0.5264 0.3552 0.4978 0.088 Uiso 1 1 calc R . .
H8B H 0.6661 0.3394 0.5744 0.088 Uiso 1 1 calc R . .
C9 C 0.6357(4) 0.4598(3) 0.4403(5) 0.1026(14) Uani 1 1 d . . .
H9A H 0.6730 0.5180 0.5026 0.123 Uiso 1 1 calc R . .
H9B H 0.5619 0.4933 0.3826 0.123 Uiso 1 1 calc R . .
C10 C 0.7221(4) 0.4238(3) 0.3791(5) 0.1090(16) Uani 1 1 d . . .
H10A H 0.7055 0.4683 0.3048 0.131 Uiso 1 1 calc R . .
H10B H 0.8054 0.4400 0.4310 0.131 Uiso 1 1 calc R . .
C11 C 0.7067(3) 0.2971(3) 0.3524(3) 0.0643(9) Uani 1 1 d . . .
H11A H 0.7846 0.2567 0.3857 0.077 Uiso 1 1 calc R . .
H11B H 0.6750 0.2844 0.2657 0.077 Uiso 1 1 calc R . .
C12 C 0.6596(2) 0.1358(2) 0.4845(3) 0.0538(7) Uani 1 1 d . . .
H12A H 0.7446 0.1460 0.5350 0.065 Uiso 1 1 calc R . .
H12B H 0.6130 0.1254 0.5375 0.065 Uiso 1 1 calc R . .
C13 C 0.6486(2) 0.0258(2) 0.4111(2) 0.0480(7) 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
O1 C5 1.336(3) . ?
O1 C4 1.468(3) . ?
O2 C5 1.209(3) . ?
O3 C13 1.206(3) . ?
O4 C13 1.318(3) . ?
O4 H4 0.8200 . ?
N1 C5 1.327(3) . ?
N1 C6 1.456(3) . ?
N1 H1 0.8600 . ?
C1 C4 1.501(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C4 1.492(5) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C4 1.517(4) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C6 C7 1.533(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C12 1.532(4) . ?
C7 C8 1.537(4) . ?
C7 C11 1.550(4) . ?
C8 C9 1.468(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.489(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.462(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.495(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 C4 122.1(2) . . ?
C13 O4 H4 109.5 . . ?
C5 N1 C6 124.3(2) . . ?
C5 N1 H1 117.8 . . ?
C6 N1 H1 117.8 . . ?
C4 C1 H1A 109.5 . . ?
C4 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C4 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C4 C2 H2A 109.5 . . ?
C4 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C4 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O1 C4 C2 110.7(3) . . ?
O1 C4 C1 109.7(3) . . ?
C2 C4 C1 112.6(4) . . ?
O1 C4 C3 102.6(2) . . ?
C2 C4 C3 110.5(3) . . ?
C1 C4 C3 110.3(3) . . ?
O2 C5 N1 124.8(3) . . ?
O2 C5 O1 124.1(2) . . ?
N1 C5 O1 111.1(2) . . ?
N1 C6 C7 114.2(2) . . ?
N1 C6 H6A 108.7 . . ?
C7 C6 H6A 108.7 . . ?
N1 C6 H6B 108.7 . . ?
C7 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
C12 C7 C6 110.1(2) . . ?
C12 C7 C8 110.1(2) . . ?
C6 C7 C8 111.8(2) . . ?
C12 C7 C11 113.7(2) . . ?
C6 C7 C11 108.2(2) . . ?
C8 C7 C11 102.9(2) . . ?
C9 C8 C7 106.4(3) . . ?
C9 C8 H8A 110.4 . . ?
C7 C8 H8A 110.4 . . ?
C9 C8 H8B 110.4 . . ?
C7 C8 H8B 110.4 . . ?
H8A C8 H8B 108.6 . . ?
C8 C9 C10 105.6(3) . . ?
C8 C9 H9A 110.6 . . ?
C10 C9 H9A 110.6 . . ?
C8 C9 H9B 110.6 . . ?
C10 C9 H9B 110.6 . . ?
H9A C9 H9B 108.8 . . ?
C11 C10 C9 108.6(3) . . ?
C11 C10 H10A 110.0 . . ?
C9 C10 H10A 110.0 . . ?
C11 C10 H10B 110.0 . . ?
C9 C10 H10B 110.0 . . ?
H10A C10 H10B 108.4 . . ?
C10 C11 C7 107.4(3) . . ?
C10 C11 H11A 110.2 . . ?
C7 C11 H11A 110.2 . . ?
C10 C11 H11B 110.2 . . ?
C7 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
C13 C12 C7 114.8(2) . . ?
C13 C12 H12A 108.6 . . ?
C7 C12 H12A 108.6 . . ?
C13 C12 H12B 108.6 . . ?
C7 C12 H12B 108.6 . . ?
H12A C12 H12B 107.5 . . ?
O3 C13 O4 122.6(3) . . ?
O3 C13 C12 123.4(2) . . ?
O4 C13 C12 114.0(2) . . ?

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
C5 O1 C4 C2 62.8(4) . . . . ?
C5 O1 C4 C1 -62.1(4) . . . . ?
C5 O1 C4 C3 -179.3(3) . . . . ?
C6 N1 C5 O2 -8.7(5) . . . . ?
C6 N1 C5 O1 171.2(3) . . . . ?
C4 O1 C5 O2 -4.2(5) . . . . ?
C4 O1 C5 N1 176.0(3) . . . . ?
C5 N1 C6 C7 131.1(3) . . . . ?
N1 C6 C7 C12 57.8(3) . . . . ?
N1 C6 C7 C8 -64.8(3) . . . . ?
N1 C6 C7 C11 -177.4(2) . . . . ?
C12 C7 C8 C9 148.2(3) . . . . ?
C6 C7 C8 C9 -89.1(3) . . . . ?
C11 C7 C8 C9 26.7(4) . . . . ?
C7 C8 C9 C10 -30.8(5) . . . . ?
C8 C9 C10 C11 22.8(5) . . . . ?
C9 C10 C11 C7 -5.7(5) . . . . ?
C12 C7 C11 C10 -131.7(3) . . . . ?
C6 C7 C11 C10 105.7(3) . . . . ?
C8 C7 C11 C10 -12.6(4) . . . . ?
C6 C7 C12 C13 45.3(3) . . . . ?
C8 C7 C12 C13 168.9(2) . . . . ?
C11 C7 C12 C13 -76.2(3) . . . . ?
C7 C12 C13 O3 -107.2(3) . . . . ?
C7 C12 C13 O4 71.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.227
_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_akdkm94_0m
_database_code_depnum_ccdc_archive 'CCDC 1845125'
_audit_update_record             
;
2018-05-24 deposited with the CCDC.	2019-02-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C H N O'
_chemical_formula_weight         43.03

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           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   9.4628(15)
_cell_length_b                   10.1211(16)
_cell_length_c                   10.7468(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.784(4)
_cell_angle_gamma                90.00
_cell_volume                     974.4(3)
_cell_formula_units_Z            19
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             418
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15073
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0365
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         32.12
_reflns_number_total             5327
_reflns_number_gt                4705
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_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)+(0.1000P)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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(8)
_refine_ls_number_reflns         5327
_refine_ls_number_parameters     223
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1377
_refine_ls_wR_factor_gt          0.1287
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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
C2 C 0.6393(2) 0.49652(19) 0.59764(18) 0.0300(4) Uani 1 1 d . . .
H2A H 0.6615 0.5590 0.5393 0.045 Uiso 1 1 calc R . .
H2B H 0.6740 0.5302 0.6858 0.045 Uiso 1 1 calc R . .
H2C H 0.5334 0.4826 0.5715 0.045 Uiso 1 1 calc R . .
C3 C 0.88498(19) 0.3842(2) 0.64687(17) 0.0372(5) Uani 1 1 d . . .
H3A H 0.9331 0.3027 0.6388 0.056 Uiso 1 1 calc R . .
H3B H 0.9125 0.4087 0.7379 0.056 Uiso 1 1 calc R . .
H3C H 0.9157 0.4522 0.5988 0.056 Uiso 1 1 calc R . .
C1 C 0.6675(2) 0.2546(2) 0.66262(17) 0.0360(4) Uani 1 1 d . . .
H1A H 0.5606 0.2479 0.6311 0.054 Uiso 1 1 calc R . .
H1B H 0.7005 0.2720 0.7554 0.054 Uiso 1 1 calc R . .
H1C H 0.7103 0.1732 0.6461 0.054 Uiso 1 1 calc R . .
C4 C 0.71662(17) 0.36691(17) 0.59167(13) 0.0219(3) Uani 1 1 d . . .
O1 O 0.69377(12) 0.32804(13) 0.45421(9) 0.0232(2) Uani 1 1 d . . .
C5 C 0.55297(16) 0.31254(15) 0.37103(13) 0.0188(3) Uani 1 1 d . . .
O2 O 0.44102(11) 0.32203(13) 0.40266(9) 0.0234(2) Uani 1 1 d . . .
N1 N 0.55470(14) 0.28598(14) 0.24905(12) 0.0211(3) Uani 1 1 d . . .
H1 H 0.6387 0.2869 0.2341 0.025 Uiso 1 1 calc R . .
C6 C 0.41932(17) 0.25565(16) 0.14135(14) 0.0199(3) Uani 1 1 d . . .
H6A H 0.3413 0.2322 0.1778 0.024 Uiso 1 1 calc R . .
H6B H 0.4379 0.1791 0.0946 0.024 Uiso 1 1 calc R . .
C7 C 0.36259(16) 0.36914(17) 0.04240(13) 0.0201(3) Uani 1 1 d . . .
C8 C 0.30584(16) 0.48748(16) 0.10565(15) 0.0209(3) Uani 1 1 d . . .
H8A H 0.3790 0.5065 0.1904 0.025 Uiso 1 1 calc R . .
H8B H 0.2985 0.5647 0.0505 0.025 Uiso 1 1 calc R . .
C9 C 0.15632(17) 0.46442(15) 0.12455(15) 0.0192(3) Uani 1 1 d . . .
O3 O 0.03693(12) 0.49149(13) 0.03660(11) 0.0258(3) Uani 1 1 d . . .
N2 N 0.15914(14) 0.41064(13) 0.23869(12) 0.0182(2) Uani 1 1 d . . .
H2 H 0.2443 0.4019 0.2989 0.022 Uiso 1 1 calc R . .
C10 C 0.02581(16) 0.36560(16) 0.26762(14) 0.0191(3) Uani 1 1 d . . .
C12 C 0.07936(19) 0.3020(2) 0.40478(15) 0.0278(4) Uani 1 1 d . . .
H12A H 0.1498 0.2332 0.4064 0.042 Uiso 1 1 calc R . .
H12B H -0.0045 0.2652 0.4245 0.042 Uiso 1 1 calc R . .
H12C H 0.1263 0.3678 0.4691 0.042 Uiso 1 1 calc R . .
C11 C -0.08071(19) 0.47948(19) 0.26518(18) 0.0292(4) Uani 1 1 d . . .
H11A H -0.0273 0.5492 0.3214 0.044 Uiso 1 1 calc R . .
H11B H -0.1598 0.4488 0.2957 0.044 Uiso 1 1 calc R . .
H11C H -0.1221 0.5121 0.1770 0.044 Uiso 1 1 calc R . .
C13 C -0.05328(16) 0.25544(16) 0.17157(14) 0.0200(3) Uani 1 1 d . . .
O5 O 0.03810(12) 0.18639(12) 0.12697(11) 0.0233(2) Uani 1 1 d . . .
H5 H -0.0079 0.1256 0.0811 0.035 Uiso 1 1 calc R . .
O4 O -0.18554(13) 0.23075(15) 0.14772(13) 0.0332(3) Uani 1 1 d . . .
C14 C 0.23946(18) 0.3135(2) -0.08113(14) 0.0305(4) Uani 1 1 d . . .
H14A H 0.2051 0.2279 -0.0621 0.037 Uiso 1 1 calc R . .
H14B H 0.1548 0.3731 -0.1087 0.037 Uiso 1 1 calc R . .
C15 C 0.48702(19) 0.4166(2) -0.01139(16) 0.0291(4) Uani 1 1 d . . .
H15A H 0.5237 0.5028 0.0239 0.035 Uiso 1 1 calc R . .
H15B H 0.5698 0.3548 0.0117 0.035 Uiso 1 1 calc R . .
C16 C 0.4141(3) 0.4233(3) -0.15977(19) 0.0429(5) Uani 1 1 d . . .
H16A H 0.4877 0.4175 -0.2048 0.052 Uiso 1 1 calc R . .
H16B H 0.3570 0.5041 -0.1860 0.052 Uiso 1 1 calc R . .
C17 C 0.3121(2) 0.3014(2) -0.18695(16) 0.0370(4) Uani 1 1 d . . .
H17A H 0.2388 0.3049 -0.2740 0.044 Uiso 1 1 calc R . .
H17B H 0.3692 0.2203 -0.1778 0.044 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
C2 C4 1.513(2) . ?
C3 C4 1.521(2) . ?
C1 C4 1.522(3) . ?
C4 O1 1.4759(17) . ?
O1 C5 1.3535(16) . ?
C5 O2 1.2161(19) . ?
C5 N1 1.3434(18) . ?
N1 C6 1.4561(18) . ?
C6 C7 1.540(2) . ?
C7 C15 1.546(2) . ?
C7 C8 1.556(2) . ?
C7 C14 1.562(2) . ?
C8 C9 1.511(2) . ?
C9 O3 1.2478(18) . ?
C9 N2 1.334(2) . ?
N2 C10 1.4658(19) . ?
C10 C11 1.526(2) . ?
C10 C12 1.537(2) . ?
C10 C13 1.540(2) . ?
C13 O4 1.2198(19) . ?
C13 O5 1.3164(19) . ?
C14 C17 1.512(2) . ?
C15 C16 1.522(2) . ?
C16 C17 1.535(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
O1 C4 C2 110.88(13) . . ?
O1 C4 C3 102.63(13) . . ?
C2 C4 C3 110.09(15) . . ?
O1 C4 C1 109.41(14) . . ?
C2 C4 C1 113.34(15) . . ?
C3 C4 C1 109.95(15) . . ?
C5 O1 C4 119.20(12) . . ?
O2 C5 N1 125.03(13) . . ?
O2 C5 O1 124.55(13) . . ?
N1 C5 O1 110.42(13) . . ?
C5 N1 C6 122.26(13) . . ?
N1 C6 C7 114.43(13) . . ?
C6 C7 C15 110.60(13) . . ?
C6 C7 C8 111.42(11) . . ?
C15 C7 C8 109.63(14) . . ?
C6 C7 C14 108.46(14) . . ?
C15 C7 C14 104.11(12) . . ?
C8 C7 C14 112.39(13) . . ?
C9 C8 C7 114.19(13) . . ?
O3 C9 N2 122.08(14) . . ?
O3 C9 C8 121.52(14) . . ?
N2 C9 C8 116.38(13) . . ?
C9 N2 C10 123.92(12) . . ?
N2 C10 C11 111.74(13) . . ?
N2 C10 C12 107.04(12) . . ?
C11 C10 C12 110.17(13) . . ?
N2 C10 C13 110.41(12) . . ?
C11 C10 C13 111.08(12) . . ?
C12 C10 C13 106.16(14) . . ?
O4 C13 O5 124.37(15) . . ?
O4 C13 C10 122.24(14) . . ?
O5 C13 C10 113.21(13) . . ?
C17 C14 C7 105.83(13) . . ?
C16 C15 C7 105.24(14) . . ?
C15 C16 C17 102.03(16) . . ?
C14 C17 C16 101.68(16) . . ?

_diffrn_measured_fraction_theta_max 0.919
_diffrn_reflns_theta_full        32.12
_diffrn_measured_fraction_theta_full 0.919
_refine_diff_density_max         0.700
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.056
####################################################################### 
# 
# 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_akd016
_database_code_depnum_ccdc_archive 'CCDC 1815432'
loop_
_audit_author_name
_audit_author_address
'Shaikh M. Mobin' 'Indian Institute of Technology Indore, India'
_audit_update_record             
;
2018-01-08 deposited with the CCDC.	2019-02-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H11.27 N0.73 O2.18'
_chemical_formula_weight         152.54

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   10.2051(2)
_cell_length_b                   12.0183(3)
_cell_length_c                   19.9352(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2445.01(9)
_cell_formula_units_Z            11
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    10806
_cell_measurement_theta_min      3.6980
_cell_measurement_theta_max      71.2460

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.140
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             900
_exptl_absorpt_coefficient_mu    0.682
_exptl_absorpt_correction_T_min  0.8063
_exptl_absorpt_correction_T_max  0.8700
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Micro-Focus (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16519
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.30
_diffrn_reflns_theta_max         71.48
_reflns_number_total             4707
_reflns_number_gt                4562
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_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.
;

_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)+(0.0803P)²+0.2761P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_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   -0.2(2)
_refine_ls_number_reflns         4707
_refine_ls_number_parameters     278
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1287
_refine_ls_wR_factor_gt          0.1234
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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 0.31816(16) -0.28548(13) 0.75156(7) 0.0609(4) Uani 1 1 d . . .
O2 O 0.82008(13) 0.16449(11) 0.52825(6) 0.0522(3) Uani 1 1 d . . .
O3 O 0.76885(16) 0.25256(13) 0.62266(7) 0.0630(4) Uani 1 1 d . . .
O4 O 0.50563(14) 0.20590(11) 0.50065(7) 0.0569(4) Uani 1 1 d . . .
O5 O 0.67352(16) -0.16764(11) 0.48210(7) 0.0575(3) Uani 1 1 d . . .
O6 O 0.66104(19) -0.29731(12) 0.39977(8) 0.0690(4) Uani 1 1 d . . .
N1 N 0.59764(13) 0.04537(11) 0.52959(7) 0.0385(3) Uani 1 1 d . . .
H1 H 0.6119 -0.0253 0.5205 0.046 Uiso 1 1 calc R . .
N2 N 0.6948(2) -0.12375(15) 0.37201(9) 0.0622(5) Uani 1 1 d . . .
H2 H 0.6854 -0.1497 0.3310 0.075 Uiso 1 1 calc R . .
C1 C 0.4094(2) -0.21403(17) 0.72531(8) 0.0498(4) Uani 1 1 d . . .
C2 C 0.4883(2) -0.25247(17) 0.67421(9) 0.0572(5) Uani 1 1 d . . .
H2A H 0.4792 -0.3267 0.6585 0.069 Uiso 1 1 calc R . .
C3 C 0.5810(2) -0.18265(17) 0.64585(9) 0.0537(4) Uani 1 1 d . . .
H3 H 0.6347 -0.2097 0.6105 0.064 Uiso 1 1 calc R . .
C4 C 0.59682(18) -0.07454(16) 0.66780(8) 0.0453(4) Uani 1 1 d . . .
C5 C 0.5163(2) -0.03698(17) 0.71926(10) 0.0571(5) Uani 1 1 d . . .
H5 H 0.5254 0.0372 0.7350 0.068 Uiso 1 1 calc R . .
C6 C 0.4229(2) -0.10589(17) 0.74794(10) 0.0587(5) Uani 1 1 d . . .
H6 H 0.3684 -0.0789 0.7830 0.070 Uiso 1 1 calc R . .
C7 C 0.69979(17) 0.00051(16) 0.63779(9) 0.0456(4) Uani 1 1 d . . .
H7A H 0.7616 -0.0453 0.6113 0.055 Uiso 1 1 calc R . .
H7B H 0.7499 0.0359 0.6746 0.055 Uiso 1 1 calc R . .
C8 C 0.64345(16) 0.09166(13) 0.59254(8) 0.0387(3) Uani 1 1 d . . .
H8 H 0.5676 0.1271 0.6160 0.046 Uiso 1 1 calc R . .
C9 C 0.74926(17) 0.17933(14) 0.58185(8) 0.0416(3) Uani 1 1 d . . .
C10 C 0.53485(15) 0.10808(14) 0.48581(8) 0.0410(3) Uani 1 1 d . . .
C11 C 0.50465(18) 0.05938(15) 0.41756(9) 0.0470(4) Uani 1 1 d . . .
H11A H 0.4245 0.0953 0.3998 0.056 Uiso 1 1 calc R . .
H11B H 0.4859 -0.0210 0.4229 0.056 Uiso 1 1 calc R . .
C12 C 0.6164(2) 0.07358(17) 0.36560(9) 0.0552(5) Uani 1 1 d . . .
C13 C 0.6701(3) 0.19424(19) 0.36302(13) 0.0756(7) Uani 1 1 d . . .
H13A H 0.6256 0.2408 0.3971 0.091 Uiso 1 1 calc R . .
H13B H 0.7653 0.1945 0.3726 0.091 Uiso 1 1 calc R . .
C14 C 0.6470(10) 0.2363(4) 0.2994(2) 0.220(5) Uani 1 1 d . . .
H14A H 0.7307 0.2405 0.2744 0.263 Uiso 1 1 calc R . .
H14B H 0.6113 0.3127 0.3031 0.263 Uiso 1 1 calc R . .
C15 C 0.5543(5) 0.1665(3) 0.26214(14) 0.1084(13) Uani 1 1 d . . .
H15A H 0.5795 0.1620 0.2143 0.130 Uiso 1 1 calc R . .
H15B H 0.4645 0.1973 0.2652 0.130 Uiso 1 1 calc R . .
C16 C 0.5608(4) 0.0551(2) 0.29396(10) 0.0797(8) Uani 1 1 d . . .
H16A H 0.6188 0.0051 0.2679 0.096 Uiso 1 1 calc R . .
H16B H 0.4724 0.0213 0.2962 0.096 Uiso 1 1 calc R . .
C17 C 0.7288(2) -0.00723(18) 0.38010(11) 0.0579(5) Uani 1 1 d . . .
H17A H 0.8027 0.0104 0.3497 0.069 Uiso 1 1 calc R . .
H17B H 0.7593 0.0048 0.4267 0.069 Uiso 1 1 calc R . .
C18 C 0.6769(2) -0.19369(15) 0.42304(10) 0.0519(4) Uani 1 1 d . . .
C19 C 0.6414(3) -0.39203(17) 0.44493(13) 0.0647(6) Uani 1 1 d . . .
C20 C 0.5141(3) -0.3782(3) 0.4830(2) 0.0951(9) Uani 1 1 d . . .
H20A H 0.4436 -0.3596 0.4516 0.143 Uiso 1 1 calc R . .
H20B H 0.5235 -0.3183 0.5160 0.143 Uiso 1 1 calc R . .
H20C H 0.4928 -0.4478 0.5062 0.143 Uiso 1 1 calc R . .
C21 C 0.7573(3) -0.4044(3) 0.49063(19) 0.0965(10) Uani 1 1 d . . .
H21A H 0.7635 -0.3392 0.5199 0.145 Uiso 1 1 calc R . .
H21B H 0.8374 -0.4106 0.4638 0.145 Uiso 1 1 calc R . .
H21C H 0.7468 -0.4715 0.5180 0.145 Uiso 1 1 calc R . .
C22 C 0.6302(5) -0.4883(2) 0.39554(19) 0.1117(13) Uani 1 1 d . . .
H22A H 0.7080 -0.4899 0.3667 0.168 Uiso 1 1 calc R . .
H22B H 0.5517 -0.4784 0.3678 0.168 Uiso 1 1 calc R . .
H22C H 0.6237 -0.5585 0.4203 0.168 Uiso 1 1 calc R . .
H101 H 0.290(3) -0.259(2) 0.7936(15) 0.074(8) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.371(2) . ?
O1 H101 0.94(3) . ?
O2 C9 1.302(2) . ?
O3 C9 1.215(2) . ?
O4 C10 1.248(2) . ?
O5 C18 1.219(2) . ?
O6 C18 1.339(2) . ?
O6 C19 1.465(3) . ?
N1 C10 1.319(2) . ?
N1 C8 1.450(2) . ?
N1 H1 0.8800 . ?
N2 C18 1.332(3) . ?
N2 C17 1.452(3) . ?
N2 H2 0.8800 . ?
C1 C2 1.378(3) . ?
C1 C6 1.383(3) . ?
C2 C3 1.385(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.380(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(3) . ?
C4 C7 1.509(2) . ?
C5 C6 1.386(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.531(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.524(2) . ?
C8 H8 1.0000 . ?
C10 C11 1.513(2) . ?
C11 C12 1.550(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C17 1.531(3) . ?
C12 C13 1.551(3) . ?
C12 C16 1.553(3) . ?
C13 C14 1.387(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.466(7) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.483(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C19 C21 1.500(4) . ?
C19 C20 1.514(4) . ?
C19 C22 1.524(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

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 O1 H101 109.4(17) . . ?
C18 O6 C19 121.77(16) . . ?
C10 N1 C8 120.66(14) . . ?
C10 N1 H1 119.7 . . ?
C8 N1 H1 119.7 . . ?
C18 N2 C17 123.83(17) . . ?
C18 N2 H2 118.1 . . ?
C17 N2 H2 118.1 . . ?
O1 C1 C2 117.98(18) . . ?
O1 C1 C6 122.15(18) . . ?
C2 C1 C6 119.86(18) . . ?
C1 C2 C3 119.83(18) . . ?
C1 C2 H2A 120.1 . . ?
C3 C2 H2A 120.1 . . ?
C4 C3 C2 121.40(18) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 118.06(17) . . ?
C3 C4 C7 121.25(17) . . ?
C5 C4 C7 120.69(17) . . ?
C6 C5 C4 121.13(18) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C1 C6 C5 119.71(19) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C4 C7 C8 113.57(15) . . ?
C4 C7 H7A 108.9 . . ?
C8 C7 H7A 108.9 . . ?
C4 C7 H7B 108.9 . . ?
C8 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
N1 C8 C9 111.88(13) . . ?
N1 C8 C7 110.89(14) . . ?
C9 C8 C7 108.12(14) . . ?
N1 C8 H8 108.6 . . ?
C9 C8 H8 108.6 . . ?
C7 C8 H8 108.6 . . ?
O3 C9 O2 123.87(16) . . ?
O3 C9 C8 121.59(15) . . ?
O2 C9 C8 114.41(14) . . ?
O4 C10 N1 119.81(15) . . ?
O4 C10 C11 121.93(15) . . ?
N1 C10 C11 118.22(15) . . ?
C10 C11 C12 114.11(15) . . ?
C10 C11 H11A 108.7 . . ?
C12 C11 H11A 108.7 . . ?
C10 C11 H11B 108.7 . . ?
C12 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C17 C12 C11 110.82(15) . . ?
C17 C12 C13 109.5(2) . . ?
C11 C12 C13 112.64(18) . . ?
C17 C12 C16 110.9(2) . . ?
C11 C12 C16 109.3(2) . . ?
C13 C12 C16 103.46(18) . . ?
C14 C13 C12 108.1(3) . . ?
C14 C13 H13A 110.1 . . ?
C12 C13 H13A 110.1 . . ?
C14 C13 H13B 110.1 . . ?
C12 C13 H13B 110.1 . . ?
H13A C13 H13B 108.4 . . ?
C13 C14 C15 111.3(4) . . ?
C13 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C14 C15 C16 105.8(3) . . ?
C14 C15 H15A 110.6 . . ?
C16 C15 H15A 110.6 . . ?
C14 C15 H15B 110.6 . . ?
C16 C15 H15B 110.6 . . ?
H15A C15 H15B 108.7 . . ?
C15 C16 C12 106.3(2) . . ?
C15 C16 H16A 110.5 . . ?
C12 C16 H16A 110.5 . . ?
C15 C16 H16B 110.5 . . ?
C12 C16 H16B 110.5 . . ?
H16A C16 H16B 108.7 . . ?
N2 C17 C12 114.32(19) . . ?
N2 C17 H17A 108.7 . . ?
C12 C17 H17A 108.7 . . ?
N2 C17 H17B 108.7 . . ?
C12 C17 H17B 108.7 . . ?
H17A C17 H17B 107.6 . . ?
O5 C18 N2 125.41(18) . . ?
O5 C18 O6 124.77(19) . . ?
N2 C18 O6 109.82(17) . . ?
O6 C19 C21 110.0(2) . . ?
O6 C19 C20 109.9(2) . . ?
C21 C19 C20 112.5(3) . . ?
O6 C19 C22 101.7(2) . . ?
C21 C19 C22 112.1(3) . . ?
C20 C19 C22 110.1(3) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

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
O1 C1 C2 C3 179.38(19) . . . . ?
C6 C1 C2 C3 0.1(3) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C2 C3 C4 C7 178.67(19) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C7 C4 C5 C6 -178.9(2) . . . . ?
O1 C1 C6 C5 -179.6(2) . . . . ?
C2 C1 C6 C5 -0.3(3) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
C3 C4 C7 C8 107.5(2) . . . . ?
C5 C4 C7 C8 -73.5(2) . . . . ?
C10 N1 C8 C9 -65.31(19) . . . . ?
C10 N1 C8 C7 173.89(14) . . . . ?
C4 C7 C8 N1 -72.80(19) . . . . ?
C4 C7 C8 C9 164.20(15) . . . . ?
N1 C8 C9 O3 154.78(18) . . . . ?
C7 C8 C9 O3 -82.8(2) . . . . ?
N1 C8 C9 O2 -29.2(2) . . . . ?
C7 C8 C9 O2 93.21(18) . . . . ?
C8 N1 C10 O4 -5.5(2) . . . . ?
C8 N1 C10 C11 172.37(15) . . . . ?
O4 C10 C11 C12 91.1(2) . . . . ?
N1 C10 C11 C12 -86.8(2) . . . . ?
C10 C11 C12 C17 74.9(2) . . . . ?
C10 C11 C12 C13 -48.2(2) . . . . ?
C10 C11 C12 C16 -162.60(18) . . . . ?
C17 C12 C13 C14 118.5(5) . . . . ?
C11 C12 C13 C14 -117.6(5) . . . . ?
C16 C12 C13 C14 0.2(5) . . . . ?
C12 C13 C14 C15 13.7(7) . . . . ?
C13 C14 C15 C16 -22.6(7) . . . . ?
C14 C15 C16 C12 21.5(5) . . . . ?
C17 C12 C16 C15 -130.9(3) . . . . ?
C11 C12 C16 C15 106.7(3) . . . . ?
C13 C12 C16 C15 -13.5(3) . . . . ?
C18 N2 C17 C12 -106.3(2) . . . . ?
C11 C12 C17 N2 65.4(2) . . . . ?
C13 C12 C17 N2 -169.69(17) . . . . ?
C16 C12 C17 N2 -56.1(3) . . . . ?
C17 N2 C18 O5 7.8(4) . . . . ?
C17 N2 C18 O6 -173.2(2) . . . . ?
C19 O6 C18 O5 -1.9(3) . . . . ?
C19 O6 C18 N2 179.1(2) . . . . ?
C18 O6 C19 C21 -60.5(3) . . . . ?
C18 O6 C19 C20 63.9(3) . . . . ?
C18 O6 C19 C22 -179.5(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        71.48
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.070
