# 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 2016

####################################################################### 
# 
# 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_spider-15055
_database_code_depnum_ccdc_archive 'CCDC 1423261'
_audit_update_record             
;
2015-09-09 deposited with the CCDC.
2016-01-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H20 N2 O3'
_chemical_formula_sum            'C16 H20 N2 O3'
_chemical_formula_weight         288.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   6.53400(10)
_cell_length_b                   25.7728(5)
_cell_length_c                   8.4563(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.402(7)
_cell_angle_gamma                90
_cell_volume                     1412.17(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    25885
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.902
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private Communication'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID imaging plate'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number            38962
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.162
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3235
_reflns_number_gt                2638
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_computing_publication_material  'SHELXL-2013/2 (Sheldrick, 2014)'
_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. 

Unless stated otherwise, the hydrogen atoms were first found in the difference map, then generated geometrically and refined as riding atoms with C-H distances = 0.95- 0.99 angstroms and Uiso(H) = 1.2 times Ueq(C) for CH and CH2 groups and Uiso~(H) 
 = 1.5 times Ueq(C) for CH3 groups. Hydrogen H1 was found in the difference map and freely refined. Atoms H1 and H13 are apart of refined hydrogen bond distances.  However, H13 was geometrically placed, but the donor/acceptor distance of C13/O1 is freely refined. The donor/acceptor pair which involved H1 is between N1 and N2_$1 where _$1 denotes the symmetry operation x-1/2, -y+1/2, z+1/2.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0499P)²+0.3900P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3235
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1081
_refine_ls_wR_factor_gt          0.1033
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_restrained_S_all      1.145
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.01731(15) 0.40678(4) 0.23952(11) 0.0234(2) Uani 1 1 d . . . . .
O2 O 0.35371(15) 0.46302(4) 0.80074(11) 0.0238(2) Uani 1 1 d . . . . .
O3 O 0.49138(17) 0.39519(4) 0.94267(12) 0.0305(3) Uani 1 1 d . . . . .
N1 N 0.84278(18) 0.32968(4) 0.22475(13) 0.0184(2) Uani 1 1 d . . . . .
H1 H 0.738(3) 0.3112(7) 0.261(2) 0.031(4) Uiso 1 1 d . . . . .
N2 N 1.05060(18) 0.25096(4) -0.16095(13) 0.0217(3) Uani 1 1 d . . . . .
C1 C 0.2372(2) 0.47509(6) 0.93080(17) 0.0248(3) Uani 1 1 d . . . . .
H1A H 0.1600 0.5074 0.9070 0.037 Uiso 1 1 calc R U . . .
H1B H 0.3322 0.4793 1.0295 0.037 Uiso 1 1 calc R U . . .
H1C H 0.1407 0.4468 0.9438 0.037 Uiso 1 1 calc R U . . .
C2 C 0.4768(2) 0.42100(5) 0.82269(16) 0.0192(3) Uani 1 1 d . . . . .
C3 C 0.5887(2) 0.41061(5) 0.67905(15) 0.0169(3) Uani 1 1 d . . . . .
C4 C 0.7357(2) 0.36483(6) 0.71510(17) 0.0278(3) Uani 1 1 d . . . . .
H4A H 0.6597 0.3350 0.7526 0.033 Uiso 1 1 calc R U . . .
H4B H 0.8468 0.3745 0.8010 0.033 Uiso 1 1 calc R U . . .
C5 C 0.8310(2) 0.34929(5) 0.56441(15) 0.0181(3) Uani 1 1 d . . . . .
H5A H 0.7759 0.3152 0.5257 0.022 Uiso 1 1 calc R U . . .
H5B H 0.9826 0.3461 0.5905 0.022 Uiso 1 1 calc R U . . .
C6 C 0.77945(19) 0.39053(5) 0.43255(15) 0.0160(3) Uani 1 1 d . . . . .
C7 C 0.4327(2) 0.39757(5) 0.53227(16) 0.0211(3) Uani 1 1 d . . . . .
H7A H 0.3270 0.4252 0.5156 0.025 Uiso 1 1 calc R U . . .
H7B H 0.3621 0.3645 0.5505 0.025 Uiso 1 1 calc R U . . .
C8 C 0.54369(19) 0.39267(5) 0.38299(15) 0.0173(3) Uani 1 1 d . . . . .
H8A H 0.5087 0.4228 0.3119 0.021 Uiso 1 1 calc R U . . .
H8B H 0.4973 0.3608 0.3237 0.021 Uiso 1 1 calc R U . . .
C9 C 0.7152(2) 0.45797(5) 0.63765(17) 0.0228(3) Uani 1 1 d . . . . .
H9A H 0.8072 0.4694 0.7336 0.027 Uiso 1 1 calc R U . . .
H9B H 0.6211 0.4870 0.6022 0.027 Uiso 1 1 calc R U . . .
C10 C 0.8459(2) 0.44375(5) 0.50355(16) 0.0190(3) Uani 1 1 d . . . . .
H10A H 0.8272 0.4705 0.4189 0.023 Uiso 1 1 calc R U . . .
H10B H 0.9939 0.4428 0.5473 0.023 Uiso 1 1 calc R U . . .
C11 C 0.8926(2) 0.37775(5) 0.28975(15) 0.0175(3) Uani 1 1 d . . . . .
C12 C 0.9171(2) 0.30618(5) 0.09417(15) 0.0172(3) Uani 1 1 d . . . . .
C13 C 1.1004(2) 0.31986(5) 0.03526(15) 0.0184(3) Uani 1 1 d . . . . .
H13 H 1.1823 0.3481 0.0794 0.022 Uiso 1 1 calc R U . . .
C14 C 1.1583(2) 0.29075(5) -0.09019(16) 0.0203(3) Uani 1 1 d . . . . .
H14 H 1.2840 0.2998 -0.1287 0.024 Uiso 1 1 calc R U . . .
C15 C 0.8725(2) 0.23942(5) -0.10437(16) 0.0201(3) Uani 1 1 d . . . . .
H15 H 0.7908 0.2120 -0.1538 0.024 Uiso 1 1 calc R U . . .
C16 C 0.8016(2) 0.26509(5) 0.02108(15) 0.0183(3) Uani 1 1 d . . . . .
H16 H 0.6758 0.2550 0.0573 0.022 Uiso 1 1 calc R U . . .


_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 C11 1.2220(16) . ?
O2 C2 1.3474(16) . ?
O2 C1 1.4498(15) . ?
O3 C2 1.2066(16) . ?
N1 C11 1.3772(17) . ?
N1 C12 1.3999(16) . ?
N1 H1 0.917(18) . ?
N2 C14 1.3405(18) . ?
N2 C15 1.3473(17) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.5202(17) . ?
C3 C4 1.5272(18) . ?
C3 C7 1.5385(18) . ?
C3 C9 1.5397(18) . ?
C4 C5 1.5414(18) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.5459(17) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C11 1.5308(17) . ?
C6 C10 1.5373(17) . ?
C6 C8 1.5445(17) . ?
C7 C8 1.5400(18) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.5488(18) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C12 C16 1.3972(19) . ?
C12 C13 1.4002(18) . ?
C13 C14 1.3912(18) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.3800(18) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O2 C1 115.49(10) . . ?
C11 N1 C12 128.02(11) . . ?
C11 N1 H1 119.0(11) . . ?
C12 N1 H1 112.6(11) . . ?
C14 N2 C15 116.00(11) . . ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O3 C2 O2 122.68(12) . . ?
O3 C2 C3 125.50(12) . . ?
O2 C2 C3 111.81(11) . . ?
C2 C3 C4 109.37(11) . . ?
C2 C3 C7 110.25(10) . . ?
C4 C3 C7 109.07(11) . . ?
C2 C3 C9 111.70(11) . . ?
C4 C3 C9 108.39(11) . . ?
C7 C3 C9 108.01(11) . . ?
C3 C4 C5 110.27(11) . . ?
C3 C4 H4A 109.6 . . ?
C5 C4 H4A 109.6 . . ?
C3 C4 H4B 109.6 . . ?
C5 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C4 C5 C6 110.12(10) . . ?
C4 C5 H5A 109.6 . . ?
C6 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
C6 C5 H5B 109.6 . . ?
H5A C5 H5B 108.2 . . ?
C11 C6 C10 111.05(10) . . ?
C11 C6 C8 111.09(10) . . ?
C10 C6 C8 107.21(10) . . ?
C11 C6 C5 109.78(10) . . ?
C10 C6 C5 107.90(11) . . ?
C8 C6 C5 109.72(10) . . ?
C3 C7 C8 110.25(10) . . ?
C3 C7 H7A 109.6 . . ?
C8 C7 H7A 109.6 . . ?
C3 C7 H7B 109.6 . . ?
C8 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C7 C8 C6 109.82(10) . . ?
C7 C8 H8A 109.7 . . ?
C6 C8 H8A 109.7 . . ?
C7 C8 H8B 109.7 . . ?
C6 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C3 C9 C10 109.98(10) . . ?
C3 C9 H9A 109.7 . . ?
C10 C9 H9A 109.7 . . ?
C3 C9 H9B 109.7 . . ?
C10 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C6 C10 C9 110.03(10) . . ?
C6 C10 H10A 109.7 . . ?
C9 C10 H10A 109.7 . . ?
C6 C10 H10B 109.7 . . ?
C9 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
O1 C11 N1 123.09(12) . . ?
O1 C11 C6 123.64(12) . . ?
N1 C11 C6 113.27(11) . . ?
C16 C12 N1 117.04(12) . . ?
C16 C12 C13 118.11(12) . . ?
N1 C12 C13 124.82(12) . . ?
C14 C13 C12 117.70(12) . . ?
C14 C13 H13 121.1 . . ?
C12 C13 H13 121.1 . . ?
N2 C14 C13 125.03(12) . . ?
N2 C14 H14 117.5 . . ?
C13 C14 H14 117.5 . . ?
N2 C15 C16 123.92(13) . . ?
N2 C15 H15 118.0 . . ?
C16 C15 H15 118.0 . . ?
C15 C16 C12 119.21(12) . . ?
C15 C16 H16 120.4 . . ?
C12 C16 H16 120.4 . . ?

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 O2 C2 O3 -0.62(19) . . . . ?
C1 O2 C2 C3 178.65(11) . . . . ?
O3 C2 C3 C4 -4.38(19) . . . . ?
O2 C2 C3 C4 176.38(12) . . . . ?
O3 C2 C3 C7 115.54(15) . . . . ?
O2 C2 C3 C7 -63.70(14) . . . . ?
O3 C2 C3 C9 -124.36(15) . . . . ?
O2 C2 C3 C9 56.40(15) . . . . ?
C2 C3 C4 C5 173.07(11) . . . . ?
C7 C3 C4 C5 52.43(15) . . . . ?
C9 C3 C4 C5 -64.94(15) . . . . ?
C3 C4 C5 C6 10.07(16) . . . . ?
C4 C5 C6 C11 174.25(11) . . . . ?
C4 C5 C6 C10 53.10(14) . . . . ?
C4 C5 C6 C8 -63.39(14) . . . . ?
C2 C3 C7 C8 174.09(11) . . . . ?
C4 C3 C7 C8 -65.81(14) . . . . ?
C9 C3 C7 C8 51.79(14) . . . . ?
C3 C7 C8 C6 12.22(15) . . . . ?
C11 C6 C8 C7 171.72(10) . . . . ?
C10 C6 C8 C7 -66.78(13) . . . . ?
C5 C6 C8 C7 50.15(13) . . . . ?
C2 C3 C9 C10 173.58(11) . . . . ?
C4 C3 C9 C10 53.03(14) . . . . ?
C7 C3 C9 C10 -65.01(14) . . . . ?
C11 C6 C10 C9 174.88(11) . . . . ?
C8 C6 C10 C9 53.35(14) . . . . ?
C5 C6 C10 C9 -64.76(13) . . . . ?
C3 C9 C10 C6 10.39(15) . . . . ?
C12 N1 C11 O1 -1.3(2) . . . . ?
C12 N1 C11 C6 179.80(12) . . . . ?
C10 C6 C11 O1 -0.70(18) . . . . ?
C8 C6 C11 O1 118.52(14) . . . . ?
C5 C6 C11 O1 -119.94(14) . . . . ?
C10 C6 C11 N1 178.19(11) . . . . ?
C8 C6 C11 N1 -62.59(14) . . . . ?
C5 C6 C11 N1 58.95(14) . . . . ?
C11 N1 C12 C16 -161.31(12) . . . . ?
C11 N1 C12 C13 20.7(2) . . . . ?
C16 C12 C13 C14 -1.51(18) . . . . ?
N1 C12 C13 C14 176.51(12) . . . . ?
C15 N2 C14 C13 0.47(19) . . . . ?
C12 C13 C14 N2 1.0(2) . . . . ?
C14 N2 C15 C16 -1.54(19) . . . . ?
N2 C15 C16 C12 1.0(2) . . . . ?
N1 C12 C16 C15 -177.62(11) . . . . ?
C13 C12 C16 C15 0.56(19) . . . . ?

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
N1 H1 N2 0.917(18) 2.171(18) 3.0617(15) 163.6(15) 4_566
C13 H13 O1 0.95 2.38 2.9218(16) 115.9 .

_refine_diff_density_max         0.374
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_mini-15024
_database_code_depnum_ccdc_archive 'CCDC 1423262'
_audit_update_record             
;
2015-09-09 deposited with the CCDC.
2016-01-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H22 N2 O3'
_chemical_formula_sum            'C17 H22 N2 O3'
_chemical_formula_weight         302.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1666(8)
_cell_length_b                   10.5180(12)
_cell_length_c                   20.800(3)
_cell_angle_alpha                75.729(5)
_cell_angle_beta                 82.329(6)
_cell_angle_gamma                82.895(6)
_cell_volume                     1499.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    11757
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.820
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private Communication'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku Mercury275R CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 6.8
_diffrn_reflns_number            12190
_diffrn_reflns_av_unetI/netI     0.0986
_diffrn_reflns_av_R_equivalents  0.0728
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.049
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_full        25.025
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5281
_reflns_number_gt                3493
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Dolomanov, O.V.; Bourhis, L.J.; Gildea, R.J.; Howard, J.A.K.; Puschmann, H., 
OLEX2: A complete structure solution, refinement and analysis program
(2009). J. Appl. Cryst., 42, 339-341.
;
_computing_publication_material  'SHELXL-2013/2 (Sheldrick, 2014)'
_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 hydrogen atoms were first found in the difference map, then generated 
 geometrically and refined as riding atoms with C-H distances = 0.95- 0.99 
 Å and Uiso(H) = 1.2 times Ueq(C) for CH and CH2 groups and Uiso(H) 
 = 1.5 times Ueq(C) for CH3 groups.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0297P)²+1.2532P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5281
_refine_ls_number_parameters     401
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1399
_refine_ls_R_factor_gt           0.0837
_refine_ls_wR_factor_ref         0.1324
_refine_ls_wR_factor_gt          0.1191
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_restrained_S_all      1.130
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4857(3) 0.7554(2) 0.49863(11) 0.0257(6) Uani 1 1 d . . . . .
O2 O 0.4247(3) 0.8452(2) 0.58678(12) 0.0314(7) Uani 1 1 d . . . . .
O3 O 1.2394(4) 0.4926(2) 0.68869(12) 0.0312(7) Uani 1 1 d . . . . .
N1 N 1.1893(4) 0.3012(3) 0.66953(14) 0.0202(7) Uani 1 1 d . . . . .
N2 N 0.8634(4) -0.0103(3) 0.67412(14) 0.0238(7) Uani 1 1 d . . . . .
C1 C 0.3439(5) 0.8503(4) 0.46618(18) 0.0295(9) Uani 1 1 d . . . . .
H1A H 0.3167 0.8249 0.4264 0.044 Uiso 1 1 calc R U . . .
H1B H 0.3907 0.9377 0.4532 0.044 Uiso 1 1 calc R U . . .
H1C H 0.2281 0.8526 0.4970 0.044 Uiso 1 1 calc R U . . .
C2 C 0.5148(5) 0.7643(3) 0.56004(17) 0.0199(8) Uani 1 1 d . . . . .
C3 C 0.6740(5) 0.6668(3) 0.58790(16) 0.0181(8) Uani 1 1 d . . . . .
C4 C 0.8600(5) 0.7306(4) 0.56438(19) 0.0281(9) Uani 1 1 d . . . . .
H4A H 0.8778 0.7552 0.5150 0.034 Uiso 1 1 calc R U . . .
H4B H 0.8543 0.8119 0.5807 0.034 Uiso 1 1 calc R U . . .
C5 C 1.0270(5) 0.6358(3) 0.59029(18) 0.0243(9) Uani 1 1 d . . . . .
H5A H 1.0990 0.6787 0.6151 0.029 Uiso 1 1 calc R U . . .
H5B H 1.1126 0.6147 0.5521 0.029 Uiso 1 1 calc R U . . .
C6 C 0.6490(5) 0.6348(4) 0.66447(17) 0.0285(9) Uani 1 1 d . . . . .
H6A H 0.6348 0.7177 0.6799 0.034 Uiso 1 1 calc R U . . .
H6B H 0.5325 0.5899 0.6811 0.034 Uiso 1 1 calc R U . . .
C7 C 0.8183(5) 0.5466(4) 0.69292(17) 0.0248(9) Uani 1 1 d . . . . .
H7A H 0.7740 0.4663 0.7244 0.030 Uiso 1 1 calc R U . . .
H7B H 0.8828 0.5938 0.7179 0.030 Uiso 1 1 calc R U . . .
C8 C 0.6921(5) 0.5391(3) 0.56481(18) 0.0259(9) Uani 1 1 d . . . . .
H8A H 0.7181 0.5586 0.5156 0.031 Uiso 1 1 calc R U . . .
H8B H 0.5712 0.4983 0.5774 0.031 Uiso 1 1 calc R U . . .
C9 C 0.8524(5) 0.4417(3) 0.59614(17) 0.0222(9) Uani 1 1 d . . . . .
H9A H 0.7986 0.3627 0.6256 0.027 Uiso 1 1 calc R U . . .
H9B H 0.9410 0.4132 0.5605 0.027 Uiso 1 1 calc R U . . .
C10 C 0.9595(5) 0.5069(3) 0.63669(16) 0.0178(8) Uani 1 1 d . . . . .
C11 C 1.1351(5) 0.4312(3) 0.66806(16) 0.0204(8) Uani 1 1 d . . . . .
C12 C 1.0729(5) 0.1997(3) 0.66971(16) 0.0171(8) Uani 1 1 d . . . . .
C13 C 1.1226(5) 0.1183(3) 0.62602(17) 0.0209(8) Uani 1 1 d . . . . .
H13 H 1.2293 0.1327 0.5936 0.025 Uiso 1 1 calc R U . . .
C14 C 1.0156(5) 0.0160(4) 0.62998(18) 0.0250(9) Uani 1 1 d . . . . .
H14 H 1.0519 -0.0392 0.5996 0.030 Uiso 1 1 calc R U . . .
C15 C 0.8180(5) 0.0677(3) 0.71660(17) 0.0218(9) Uani 1 1 d . . . . .
H15 H 0.7110 0.0505 0.7486 0.026 Uiso 1 1 calc R U . . .
C16 C 0.9180(5) 0.1725(3) 0.71684(17) 0.0219(8) Uani 1 1 d . . . . .
H16 H 0.8810 0.2246 0.7486 0.026 Uiso 1 1 calc R U . . .
C17 C 1.3768(5) 0.2473(4) 0.69191(19) 0.0270(9) Uani 1 1 d . . . . .
H17A H 1.3651 0.2197 0.7407 0.041 Uiso 1 1 calc R U . . .
H17B H 1.4653 0.3153 0.6768 0.041 Uiso 1 1 calc R U . . .
H17C H 1.4241 0.1712 0.6731 0.041 Uiso 1 1 calc R U . . .
O4 O 0.7489(3) 0.1144(2) 0.87921(11) 0.0256(6) Uani 1 1 d . . . . .
O5 O 0.7209(4) 0.1197(2) 0.98671(12) 0.0319(7) Uani 1 1 d . . . . .
O6 O -0.1311(3) 0.4710(2) 0.90427(11) 0.0226(6) Uani 1 1 d . . . . .
N3 N 0.0096(4) 0.6439(3) 0.84004(14) 0.0179(7) Uani 1 1 d . . . . .
N4 N 0.4261(4) 0.9143(3) 0.79809(14) 0.0196(7) Uani 1 1 d . . . . .
C18 C 0.9010(5) 0.0112(3) 0.89291(18) 0.0261(9) Uani 1 1 d . . . . .
H18A H 0.9623 -0.0080 0.8509 0.039 Uiso 1 1 calc R U . . .
H18B H 0.8501 -0.0684 0.9215 0.039 Uiso 1 1 calc R U . . .
H18C H 0.9938 0.0399 0.9156 0.039 Uiso 1 1 calc R U . . .
C19 C 0.6661(5) 0.1592(3) 0.93253(18) 0.0196(8) Uani 1 1 d . . . . .
C20 C 0.4989(5) 0.2593(3) 0.91508(17) 0.0181(8) Uani 1 1 d . . . . .
C21 C 0.4413(5) 0.3336(3) 0.97033(16) 0.0216(9) Uani 1 1 d . . . . .
H21A H 0.5361 0.3956 0.9688 0.026 Uiso 1 1 calc R U . . .
H21B H 0.4373 0.2704 1.0144 0.026 Uiso 1 1 calc R U . . .
C22 C 0.2453(5) 0.4107(3) 0.96150(16) 0.0195(8) Uani 1 1 d . . . . .
H22A H 0.2433 0.4975 0.9723 0.023 Uiso 1 1 calc R U . . .
H22B H 0.1469 0.3613 0.9921 0.023 Uiso 1 1 calc R U . . .
C23 C 0.3288(5) 0.1890(3) 0.90744(17) 0.0208(8) Uani 1 1 d . . . . .
H23A H 0.3685 0.1294 0.8769 0.025 Uiso 1 1 calc R U . . .
H23B H 0.2804 0.1356 0.9513 0.025 Uiso 1 1 calc R U . . .
C24 C 0.1730(5) 0.2943(3) 0.87906(18) 0.0222(9) Uani 1 1 d . . . . .
H24A H 0.1728 0.2988 0.8310 0.027 Uiso 1 1 calc R U . . .
H24B H 0.0481 0.2692 0.9020 0.027 Uiso 1 1 calc R U . . .
C25 C 0.5403(5) 0.3597(3) 0.84851(16) 0.0164(8) Uani 1 1 d . . . . .
H25A H 0.5447 0.3168 0.8109 0.020 Uiso 1 1 calc R U . . .
H25B H 0.6646 0.3930 0.8468 0.020 Uiso 1 1 calc R U . . .
C26 C 0.3826(4) 0.4755(3) 0.84245(16) 0.0153(8) Uani 1 1 d . . . . .
H26A H 0.4264 0.5504 0.8553 0.018 Uiso 1 1 calc R U . . .
H26B H 0.3526 0.5052 0.7957 0.018 Uiso 1 1 calc R U . . .
C27 C 0.2045(4) 0.4300(3) 0.88841(16) 0.0155(8) Uani 1 1 d . . . . .
C28 C 0.0178(5) 0.5172(3) 0.87896(16) 0.0165(8) Uani 1 1 d . . . . .
C29 C 0.1581(5) 0.7311(3) 0.82622(17) 0.0163(8) Uani 1 1 d . . . . .
C30 C 0.2259(5) 0.7849(3) 0.76118(17) 0.0193(8) Uani 1 1 d . . . . .
H30 H 0.1820 0.7611 0.7250 0.023 Uiso 1 1 calc R U . . .
C31 C 0.3589(5) 0.8743(3) 0.74991(17) 0.0204(8) Uani 1 1 d . . . . .
H31 H 0.4062 0.9099 0.7050 0.024 Uiso 1 1 calc R U . . .
C32 C 0.3586(5) 0.8596(3) 0.86076(17) 0.0183(8) Uani 1 1 d . . . . .
H32 H 0.4052 0.8847 0.8960 0.022 Uiso 1 1 calc R U . . .
C33 C 0.2249(5) 0.7687(3) 0.87750(17) 0.0171(8) Uani 1 1 d . . . . .
H33 H 0.1807 0.7334 0.9228 0.020 Uiso 1 1 calc R U . . .
C34 C -0.1801(5) 0.7128(3) 0.83011(18) 0.0236(9) Uani 1 1 d . . . . .
H34A H -0.2331 0.7434 0.8702 0.035 Uiso 1 1 calc R U . . .
H34B H -0.2625 0.6522 0.8218 0.035 Uiso 1 1 calc R U . . .
H34C H -0.1706 0.7884 0.7918 0.035 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.348(4) . ?
O1 C1 1.444(4) . ?
O2 C2 1.205(4) . ?
O3 C11 1.226(4) . ?
N1 C11 1.368(4) . ?
N1 C12 1.433(4) . ?
N1 C17 1.481(4) . ?
N2 C15 1.332(4) . ?
N2 C14 1.338(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.511(5) . ?
C3 C8 1.519(5) . ?
C3 C4 1.533(5) . ?
C3 C6 1.535(5) . ?
C4 C5 1.526(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C10 1.548(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.525(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C10 1.545(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.541(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.536(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.536(5) . ?
C12 C13 1.381(4) . ?
C12 C16 1.388(5) . ?
C13 C14 1.377(5) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.389(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
O4 C19 1.348(4) . ?
O4 C18 1.444(4) . ?
O5 C19 1.201(4) . ?
O6 C28 1.226(4) . ?
N3 C28 1.378(4) . ?
N3 C29 1.444(4) . ?
N3 C34 1.474(4) . ?
N4 C32 1.340(4) . ?
N4 C31 1.342(4) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.514(5) . ?
C20 C21 1.529(4) . ?
C20 C25 1.539(4) . ?
C20 C23 1.546(5) . ?
C21 C22 1.542(4) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C27 1.546(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.539(5) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C27 1.534(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.549(4) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.540(4) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.533(5) . ?
C29 C30 1.379(5) . ?
C29 C33 1.384(4) . ?
C30 C31 1.378(5) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 C33 1.388(4) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 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
C2 O1 C1 116.2(3) . . ?
C11 N1 C12 128.2(3) . . ?
C11 N1 C17 117.1(3) . . ?
C12 N1 C17 112.4(3) . . ?
C15 N2 C14 116.6(3) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 O1 121.8(3) . . ?
O2 C2 C3 126.0(3) . . ?
O1 C2 C3 112.2(3) . . ?
C2 C3 C8 113.2(3) . . ?
C2 C3 C4 108.2(3) . . ?
C8 C3 C4 107.9(3) . . ?
C2 C3 C6 110.6(3) . . ?
C8 C3 C6 109.0(3) . . ?
C4 C3 C6 107.7(3) . . ?
C5 C4 C3 110.6(3) . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C4 C5 C10 111.2(3) . . ?
C4 C5 H5A 109.4 . . ?
C10 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
C10 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C7 C6 C3 111.0(3) . . ?
C7 C6 H6A 109.4 . . ?
C3 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
C3 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C6 C7 C10 110.9(3) . . ?
C6 C7 H7A 109.5 . . ?
C10 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C10 C7 H7B 109.5 . . ?
H7A C7 H7B 108.0 . . ?
C3 C8 C9 111.2(3) . . ?
C3 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
C3 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C10 C9 C8 110.3(3) . . ?
C10 C9 H9A 109.6 . . ?
C8 C9 H9A 109.6 . . ?
C10 C9 H9B 109.6 . . ?
C8 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C9 C10 C11 119.3(3) . . ?
C9 C10 C7 108.2(3) . . ?
C11 C10 C7 108.0(3) . . ?
C9 C10 C5 107.9(3) . . ?
C11 C10 C5 105.9(3) . . ?
C7 C10 C5 107.0(3) . . ?
O3 C11 N1 118.1(3) . . ?
O3 C11 C10 118.2(3) . . ?
N1 C11 C10 123.5(3) . . ?
C13 C12 C16 118.0(3) . . ?
C13 C12 N1 120.2(3) . . ?
C16 C12 N1 121.6(3) . . ?
C14 C13 C12 119.2(3) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
N2 C14 C13 123.8(3) . . ?
N2 C14 H14 118.1 . . ?
C13 C14 H14 118.1 . . ?
N2 C15 C16 123.8(3) . . ?
N2 C15 H15 118.1 . . ?
C16 C15 H15 118.1 . . ?
C12 C16 C15 118.6(3) . . ?
C12 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 O4 C18 115.0(3) . . ?
C28 N3 C29 126.1(3) . . ?
C28 N3 C34 116.9(3) . . ?
C29 N3 C34 113.8(3) . . ?
C32 N4 C31 115.8(3) . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O5 C19 O4 122.1(3) . . ?
O5 C19 C20 126.2(3) . . ?
O4 C19 C20 111.7(3) . . ?
C19 C20 C21 110.1(3) . . ?
C19 C20 C25 112.5(3) . . ?
C21 C20 C25 108.8(3) . . ?
C19 C20 C23 110.0(3) . . ?
C21 C20 C23 108.7(3) . . ?
C25 C20 C23 106.6(3) . . ?
C20 C21 C22 110.2(3) . . ?
C20 C21 H21A 109.6 . . ?
C22 C21 H21A 109.6 . . ?
C20 C21 H21B 109.6 . . ?
C22 C21 H21B 109.6 . . ?
H21A C21 H21B 108.1 . . ?
C21 C22 C27 108.8(3) . . ?
C21 C22 H22A 109.9 . . ?
C27 C22 H22A 109.9 . . ?
C21 C22 H22B 109.9 . . ?
C27 C22 H22B 109.9 . . ?
H22A C22 H22B 108.3 . . ?
C24 C23 C20 108.5(3) . . ?
C24 C23 H23A 110.0 . . ?
C20 C23 H23A 110.0 . . ?
C24 C23 H23B 110.0 . . ?
C20 C23 H23B 110.0 . . ?
H23A C23 H23B 108.4 . . ?
C27 C24 C23 111.0(3) . . ?
C27 C24 H24A 109.4 . . ?
C23 C24 H24A 109.4 . . ?
C27 C24 H24B 109.4 . . ?
C23 C24 H24B 109.4 . . ?
H24A C24 H24B 108.0 . . ?
C20 C25 C26 109.0(3) . . ?
C20 C25 H25A 109.9 . . ?
C26 C25 H25A 109.9 . . ?
C20 C25 H25B 109.9 . . ?
C26 C25 H25B 109.9 . . ?
H25A C25 H25B 108.3 . . ?
C27 C26 C25 109.4(3) . . ?
C27 C26 H26A 109.8 . . ?
C25 C26 H26A 109.8 . . ?
C27 C26 H26B 109.8 . . ?
C25 C26 H26B 109.8 . . ?
H26A C26 H26B 108.2 . . ?
C28 C27 C24 107.1(3) . . ?
C28 C27 C26 118.3(3) . . ?
C24 C27 C26 107.6(3) . . ?
C28 C27 C22 108.1(3) . . ?
C24 C27 C22 107.1(3) . . ?
C26 C27 C22 108.2(3) . . ?
O6 C28 N3 118.4(3) . . ?
O6 C28 C27 119.1(3) . . ?
N3 C28 C27 122.4(3) . . ?
C30 C29 C33 119.1(3) . . ?
C30 C29 N3 120.1(3) . . ?
C33 C29 N3 120.6(3) . . ?
C31 C30 C29 118.3(3) . . ?
C31 C30 H30 120.8 . . ?
C29 C30 H30 120.8 . . ?
N4 C31 C30 124.4(3) . . ?
N4 C31 H31 117.8 . . ?
C30 C31 H31 117.8 . . ?
N4 C32 C33 124.3(3) . . ?
N4 C32 H32 117.9 . . ?
C33 C32 H32 117.9 . . ?
C29 C33 C32 118.0(3) . . ?
C29 C33 H33 121.0 . . ?
C32 C33 H33 121.0 . . ?
N3 C34 H34A 109.5 . . ?
N3 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
N3 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 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
C1 O1 C2 O2 1.4(5) . . . . ?
C1 O1 C2 C3 -176.3(3) . . . . ?
O2 C2 C3 C8 150.3(4) . . . . ?
O1 C2 C3 C8 -32.1(4) . . . . ?
O2 C2 C3 C4 -90.2(4) . . . . ?
O1 C2 C3 C4 87.4(3) . . . . ?
O2 C2 C3 C6 27.5(5) . . . . ?
O1 C2 C3 C6 -154.8(3) . . . . ?
C2 C3 C4 C5 -179.3(3) . . . . ?
C8 C3 C4 C5 -56.4(4) . . . . ?
C6 C3 C4 C5 61.1(4) . . . . ?
C3 C4 C5 C10 -4.0(4) . . . . ?
C2 C3 C6 C7 -174.7(3) . . . . ?
C8 C3 C6 C7 60.1(4) . . . . ?
C4 C3 C6 C7 -56.7(4) . . . . ?
C3 C6 C7 C10 -4.0(4) . . . . ?
C2 C3 C8 C9 -178.3(3) . . . . ?
C4 C3 C8 C9 61.9(4) . . . . ?
C6 C3 C8 C9 -54.7(4) . . . . ?
C3 C8 C9 C10 -5.2(4) . . . . ?
C8 C9 C10 C11 -175.4(3) . . . . ?
C8 C9 C10 C7 60.8(4) . . . . ?
C8 C9 C10 C5 -54.7(4) . . . . ?
C6 C7 C10 C9 -55.6(4) . . . . ?
C6 C7 C10 C11 174.0(3) . . . . ?
C6 C7 C10 C5 60.4(4) . . . . ?
C4 C5 C10 C9 60.3(4) . . . . ?
C4 C5 C10 C11 -170.9(3) . . . . ?
C4 C5 C10 C7 -55.9(4) . . . . ?
C12 N1 C11 O3 157.6(3) . . . . ?
C17 N1 C11 O3 -4.0(5) . . . . ?
C12 N1 C11 C10 -27.7(5) . . . . ?
C17 N1 C11 C10 170.8(3) . . . . ?
C9 C10 C11 O3 165.9(3) . . . . ?
C7 C10 C11 O3 -70.2(4) . . . . ?
C5 C10 C11 O3 44.1(4) . . . . ?
C9 C10 C11 N1 -8.8(5) . . . . ?
C7 C10 C11 N1 115.1(3) . . . . ?
C5 C10 C11 N1 -130.6(3) . . . . ?
C11 N1 C12 C13 131.2(3) . . . . ?
C17 N1 C12 C13 -66.5(4) . . . . ?
C11 N1 C12 C16 -54.4(5) . . . . ?
C17 N1 C12 C16 107.9(4) . . . . ?
C16 C12 C13 C14 1.2(5) . . . . ?
N1 C12 C13 C14 175.8(3) . . . . ?
C15 N2 C14 C13 -1.0(5) . . . . ?
C12 C13 C14 N2 0.1(5) . . . . ?
C14 N2 C15 C16 0.4(5) . . . . ?
C13 C12 C16 C15 -1.7(5) . . . . ?
N1 C12 C16 C15 -176.2(3) . . . . ?
N2 C15 C16 C12 0.9(5) . . . . ?
C18 O4 C19 O5 3.0(5) . . . . ?
C18 O4 C19 C20 -175.6(3) . . . . ?
O5 C19 C20 C21 16.2(5) . . . . ?
O4 C19 C20 C21 -165.3(3) . . . . ?
O5 C19 C20 C25 137.8(4) . . . . ?
O4 C19 C20 C25 -43.7(4) . . . . ?
O5 C19 C20 C23 -103.5(4) . . . . ?
O4 C19 C20 C23 75.0(4) . . . . ?
C19 C20 C21 C22 -166.5(3) . . . . ?
C25 C20 C21 C22 69.7(3) . . . . ?
C23 C20 C21 C22 -46.0(4) . . . . ?
C20 C21 C22 C27 -20.6(4) . . . . ?
C19 C20 C23 C24 -171.2(3) . . . . ?
C21 C20 C23 C24 68.3(3) . . . . ?
C25 C20 C23 C24 -48.9(3) . . . . ?
C20 C23 C24 C27 -18.2(4) . . . . ?
C19 C20 C25 C26 -167.0(3) . . . . ?
C21 C20 C25 C26 -44.7(3) . . . . ?
C23 C20 C25 C26 72.3(3) . . . . ?
C20 C25 C26 C27 -21.7(3) . . . . ?
C23 C24 C27 C28 -163.2(3) . . . . ?
C23 C24 C27 C26 68.7(3) . . . . ?
C23 C24 C27 C22 -47.5(4) . . . . ?
C25 C26 C27 C28 -166.3(3) . . . . ?
C25 C26 C27 C24 -44.9(3) . . . . ?
C25 C26 C27 C22 70.5(3) . . . . ?
C21 C22 C27 C28 -175.0(3) . . . . ?
C21 C22 C27 C24 69.9(3) . . . . ?
C21 C22 C27 C26 -45.8(4) . . . . ?
C29 N3 C28 O6 156.2(3) . . . . ?
C34 N3 C28 O6 -2.0(4) . . . . ?
C29 N3 C28 C27 -27.2(5) . . . . ?
C34 N3 C28 C27 174.5(3) . . . . ?
C24 C27 C28 O6 42.8(4) . . . . ?
C26 C27 C28 O6 164.4(3) . . . . ?
C22 C27 C28 O6 -72.3(4) . . . . ?
C24 C27 C28 N3 -133.7(3) . . . . ?
C26 C27 C28 N3 -12.1(5) . . . . ?
C22 C27 C28 N3 111.2(3) . . . . ?
C28 N3 C29 C30 123.7(4) . . . . ?
C34 N3 C29 C30 -77.4(4) . . . . ?
C28 N3 C29 C33 -60.7(5) . . . . ?
C34 N3 C29 C33 98.1(4) . . . . ?
C33 C29 C30 C31 0.2(5) . . . . ?
N3 C29 C30 C31 175.8(3) . . . . ?
C32 N4 C31 C30 1.4(5) . . . . ?
C29 C30 C31 N4 -0.9(5) . . . . ?
C31 N4 C32 C33 -1.2(5) . . . . ?
C30 C29 C33 C32 -0.1(5) . . . . ?
N3 C29 C33 C32 -175.7(3) . . . . ?
N4 C32 C33 C29 0.6(5) . . . . ?

_refine_diff_density_max         0.233
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.055

