# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_dm15303
_database_code_depnum_ccdc_archive 'CCDC 1404844'
_audit_update_record             
;
2015-06-04 deposited with the CCDC.
2016-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H21 N2 O3'
_chemical_formula_weight         325.38

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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   9.6907(9)
_cell_length_b                   21.234(2)
_cell_length_c                   8.2891(8)
_cell_angle_alpha                90
_cell_angle_beta                 95.872(2)
_cell_angle_gamma                90
_cell_volume                     1696.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    5774
_cell_measurement_theta_min      4.461
_cell_measurement_theta_max      55.000

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_F_000             692
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.123
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6828
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12270
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.113
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3322
_reflns_number_gt                2873
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0638P)²+0.9310P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0106(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3322
_refine_ls_number_parameters     227
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1244
_refine_ls_wR_factor_gt          0.1205
_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

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.219 0.892 -0.038 34 22 ' '
2 0.781 0.108 0.038 34 22 ' '
3 0.219 0.608 0.462 34 22 ' '
4 0.781 0.392 0.538 34 22 ' '
_platon_squeeze_details          
;
;



loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.17143(14) 0.42533(7) 0.64700(17) 0.0194(3) Uani 1 1 d D . . . .
N2 N 0.40147(14) 0.43592(7) 0.61228(17) 0.0202(3) Uani 1 1 d D . . . .
O1 O 0.31364(13) 0.18933(6) 0.35691(17) 0.0320(3) Uani 1 1 d . . . . .
O2 O 0.36915(11) 0.40410(5) 0.30396(13) 0.0187(3) Uani 1 1 d . . . . .
O3 O 0.16303(13) 0.48154(6) 0.18967(14) 0.0249(3) Uani 1 1 d . . . . .
H3 H 0.1689 0.5148 0.2450 0.037 Uiso 1 1 calc R U . . .
C1 C 0.38388(17) 0.23321(8) 0.31579(19) 0.0204(4) Uani 1 1 d . . . . .
C2 C 0.51956(17) 0.22227(8) 0.2445(2) 0.0231(4) Uani 1 1 d . . . . .
H2A H 0.4997 0.2148 0.1265 0.028 Uiso 1 1 calc R U . . .
H2B H 0.5635 0.1837 0.2934 0.028 Uiso 1 1 calc R U . . .
C3 C 0.62197(17) 0.27674(8) 0.2709(2) 0.0236(4) Uani 1 1 d . . . . .
H3A H 0.7029 0.2683 0.2103 0.028 Uiso 1 1 calc R U . . .
H3B H 0.6556 0.2794 0.3875 0.028 Uiso 1 1 calc R U . . .
C4 C 0.55700(17) 0.33988(8) 0.2151(2) 0.0215(4) Uani 1 1 d . . . . .
H4A H 0.6190 0.3750 0.2540 0.026 Uiso 1 1 calc R U . . .
H4B H 0.5429 0.3415 0.0952 0.026 Uiso 1 1 calc R U . . .
C5 C 0.42230(16) 0.34555(7) 0.28326(18) 0.0177(3) Uani 1 1 d . . . . .
C6 C 0.34297(16) 0.29845(8) 0.32869(18) 0.0179(3) Uani 1 1 d . . . . .
C7 C 0.20957(16) 0.32510(7) 0.37763(19) 0.0172(3) Uani 1 1 d . . . . .
H7 H 0.1848 0.3080 0.4834 0.021 Uiso 1 1 calc R U . . .
C8 C 0.24379(16) 0.39691(7) 0.38470(19) 0.0169(3) Uani 1 1 d . . . . .
C9 C 0.12080(17) 0.43190(8) 0.28437(19) 0.0196(3) Uani 1 1 d . . . . .
H9 H 0.0563 0.4487 0.3607 0.023 Uiso 1 1 calc R U . . .
C10 C 0.04935(16) 0.37955(8) 0.18609(19) 0.0194(3) Uani 1 1 d . . . . .
C11 C 0.09171(16) 0.32055(8) 0.24360(19) 0.0184(3) Uani 1 1 d . . . . .
C12 C 0.03265(16) 0.26596(8) 0.1746(2) 0.0205(3) Uani 1 1 d . . . . .
H12 H 0.0604 0.2257 0.2160 0.025 Uiso 1 1 calc R U . . .
C13 C -0.06772(17) 0.27173(9) 0.0439(2) 0.0245(4) Uani 1 1 d . . . . .
H13 H -0.1090 0.2350 -0.0054 0.029 Uiso 1 1 calc R U . . .
C14 C -0.10871(17) 0.33079(9) -0.0160(2) 0.0256(4) Uani 1 1 d . . . . .
H14 H -0.1767 0.3338 -0.1068 0.031 Uiso 1 1 calc R U . . .
C15 C -0.05163(17) 0.38529(9) 0.0552(2) 0.0226(4) Uani 1 1 d . . . . .
H15 H -0.0809 0.4256 0.0154 0.027 Uiso 1 1 calc R U . . .
C16 C 0.27428(16) 0.42123(7) 0.55711(19) 0.0170(3) Uani 1 1 d . . . . .
C17 C 0.43835(17) 0.45977(8) 0.7772(2) 0.0240(4) Uani 1 1 d . . . . .
H17A H 0.5151 0.4905 0.7771 0.029 Uiso 1 1 calc R U . . .
H17B H 0.4700 0.4246 0.8501 0.029 Uiso 1 1 calc R U . . .
C18 C 0.31304(19) 0.49112(8) 0.8378(2) 0.0248(4) Uani 1 1 d . . . . .
H18A H 0.2914 0.5306 0.7767 0.030 Uiso 1 1 calc R U . . .
H18B H 0.3335 0.5019 0.9540 0.030 Uiso 1 1 calc R U . . .
C19 C 0.18947(17) 0.44705(8) 0.81577(19) 0.0209(4) Uani 1 1 d . . . . .
H19A H 0.2050 0.4106 0.8897 0.025 Uiso 1 1 calc R U . . .
H19B H 0.1049 0.4693 0.8421 0.025 Uiso 1 1 calc R U . . .
H2 H 0.4627(19) 0.4302(10) 0.552(2) 0.030(6) Uiso 1 1 d D . . . .
H1 H 0.0894(17) 0.4164(10) 0.613(2) 0.026(5) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C16 1.307(2) . ?
N1 C19 1.466(2) . ?
N1 H1 0.839(15) . ?
N2 C16 1.308(2) . ?
N2 C17 1.467(2) . ?
N2 H2 0.823(15) . ?
O1 C1 1.223(2) . ?
O2 C5 1.3633(19) . ?
O2 C8 1.4537(18) . ?
O3 C9 1.400(2) . ?
O3 H3 0.8400 . ?
C1 C6 1.448(2) . ?
C1 C2 1.514(2) . ?
C2 C3 1.525(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.532(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.479(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.339(2) . ?
C6 C7 1.504(2) . ?
C7 C11 1.513(2) . ?
C7 C8 1.560(2) . ?
C7 H7 1.0000 . ?
C8 C16 1.520(2) . ?
C8 C9 1.569(2) . ?
C9 C10 1.504(2) . ?
C9 H9 1.0000 . ?
C10 C11 1.388(2) . ?
C10 C15 1.390(2) . ?
C11 C12 1.390(2) . ?
C12 C13 1.385(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.388(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C17 C18 1.515(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.516(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?

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 N1 C19 122.78(14) . . ?
C16 N1 H1 122.8(14) . . ?
C19 N1 H1 114.4(14) . . ?
C16 N2 C17 122.62(14) . . ?
C16 N2 H2 117.7(15) . . ?
C17 N2 H2 119.7(15) . . ?
C5 O2 C8 107.85(11) . . ?
C9 O3 H3 109.5 . . ?
O1 C1 C6 122.96(15) . . ?
O1 C1 C2 121.50(15) . . ?
C6 C1 C2 115.53(14) . . ?
C1 C2 C3 113.96(14) . . ?
C1 C2 H2A 108.8 . . ?
C3 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
C3 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
C2 C3 C4 112.28(13) . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
C4 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
C5 C4 C3 107.91(13) . . ?
C5 C4 H4A 110.1 . . ?
C3 C4 H4A 110.1 . . ?
C5 C4 H4B 110.1 . . ?
C3 C4 H4B 110.1 . . ?
H4A C4 H4B 108.4 . . ?
C6 C5 O2 114.24(14) . . ?
C6 C5 C4 126.96(15) . . ?
O2 C5 C4 118.80(13) . . ?
C5 C6 C1 121.64(15) . . ?
C5 C6 C7 109.21(14) . . ?
C1 C6 C7 128.98(14) . . ?
C6 C7 C11 112.52(13) . . ?
C6 C7 C8 101.10(12) . . ?
C11 C7 C8 103.39(13) . . ?
C6 C7 H7 113.0 . . ?
C11 C7 H7 113.0 . . ?
C8 C7 H7 113.0 . . ?
O2 C8 C16 107.82(12) . . ?
O2 C8 C7 105.65(12) . . ?
C16 C8 C7 112.80(13) . . ?
O2 C8 C9 109.37(12) . . ?
C16 C8 C9 113.68(13) . . ?
C7 C8 C9 107.21(12) . . ?
O3 C9 C10 113.41(13) . . ?
O3 C9 C8 113.82(13) . . ?
C10 C9 C8 102.70(13) . . ?
O3 C9 H9 108.9 . . ?
C10 C9 H9 108.9 . . ?
C8 C9 H9 108.9 . . ?
C11 C10 C15 120.47(15) . . ?
C11 C10 C9 112.18(14) . . ?
C15 C10 C9 127.31(15) . . ?
C10 C11 C12 121.11(15) . . ?
C10 C11 C7 111.67(14) . . ?
C12 C11 C7 127.14(15) . . ?
C13 C12 C11 118.35(16) . . ?
C13 C12 H12 120.8 . . ?
C11 C12 H12 120.8 . . ?
C12 C13 C14 120.69(16) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 120.87(16) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C10 118.47(16) . . ?
C14 C15 H15 120.8 . . ?
C10 C15 H15 120.8 . . ?
N1 C16 N2 122.09(15) . . ?
N1 C16 C8 118.19(14) . . ?
N2 C16 C8 119.70(14) . . ?
N2 C17 C18 109.48(13) . . ?
N2 C17 H17A 109.8 . . ?
C18 C17 H17A 109.8 . . ?
N2 C17 H17B 109.8 . . ?
C18 C17 H17B 109.8 . . ?
H17A C17 H17B 108.2 . . ?
C17 C18 C19 109.82(14) . . ?
C17 C18 H18A 109.7 . . ?
C19 C18 H18A 109.7 . . ?
C17 C18 H18B 109.7 . . ?
C19 C18 H18B 109.7 . . ?
H18A C18 H18B 108.2 . . ?
N1 C19 C18 108.95(13) . . ?
N1 C19 H19A 109.9 . . ?
C18 C19 H19A 109.9 . . ?
N1 C19 H19B 109.9 . . ?
C18 C19 H19B 109.9 . . ?
H19A C19 H19B 108.3 . . ?

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
O1 C1 C2 C3 -153.67(16) . . . . ?
C6 C1 C2 C3 27.4(2) . . . . ?
C1 C2 C3 C4 -52.31(19) . . . . ?
C2 C3 C4 C5 48.21(18) . . . . ?
C8 O2 C5 C6 4.90(17) . . . . ?
C8 O2 C5 C4 -175.18(13) . . . . ?
C3 C4 C5 C6 -24.3(2) . . . . ?
C3 C4 C5 O2 155.83(14) . . . . ?
O2 C5 C6 C1 -179.71(14) . . . . ?
C4 C5 C6 C1 0.4(2) . . . . ?
O2 C5 C6 C7 4.71(18) . . . . ?
C4 C5 C6 C7 -175.20(14) . . . . ?
O1 C1 C6 C5 179.74(16) . . . . ?
C2 C1 C6 C5 -1.3(2) . . . . ?
O1 C1 C6 C7 -5.6(3) . . . . ?
C2 C1 C6 C7 173.28(14) . . . . ?
C5 C6 C7 C11 98.39(16) . . . . ?
C1 C6 C7 C11 -76.8(2) . . . . ?
C5 C6 C7 C8 -11.29(16) . . . . ?
C1 C6 C7 C8 173.55(15) . . . . ?
C5 O2 C8 C16 108.99(13) . . . . ?
C5 O2 C8 C7 -11.86(15) . . . . ?
C5 O2 C8 C9 -126.95(13) . . . . ?
C6 C7 C8 O2 13.66(15) . . . . ?
C11 C7 C8 O2 -102.95(13) . . . . ?
C6 C7 C8 C16 -103.88(14) . . . . ?
C11 C7 C8 C16 139.51(13) . . . . ?
C6 C7 C8 C9 130.23(12) . . . . ?
C11 C7 C8 C9 13.62(16) . . . . ?
O2 C8 C9 O3 -25.81(17) . . . . ?
C16 C8 C9 O3 94.75(16) . . . . ?
C7 C8 C9 O3 -139.90(13) . . . . ?
O2 C8 C9 C10 97.20(14) . . . . ?
C16 C8 C9 C10 -142.25(13) . . . . ?
C7 C8 C9 C10 -16.89(16) . . . . ?
O3 C9 C10 C11 137.77(14) . . . . ?
C8 C9 C10 C11 14.49(17) . . . . ?
O3 C9 C10 C15 -44.4(2) . . . . ?
C8 C9 C10 C15 -167.66(16) . . . . ?
C15 C10 C11 C12 -1.4(2) . . . . ?
C9 C10 C11 C12 176.65(14) . . . . ?
C15 C10 C11 C7 175.66(14) . . . . ?
C9 C10 C11 C7 -6.32(18) . . . . ?
C6 C7 C11 C10 -113.16(15) . . . . ?
C8 C7 C11 C10 -4.93(17) . . . . ?
C6 C7 C11 C12 63.6(2) . . . . ?
C8 C7 C11 C12 171.87(15) . . . . ?
C10 C11 C12 C13 1.5(2) . . . . ?
C7 C11 C12 C13 -175.03(15) . . . . ?
C11 C12 C13 C14 -0.3(2) . . . . ?
C12 C13 C14 C15 -1.0(2) . . . . ?
C13 C14 C15 C10 1.1(2) . . . . ?
C11 C10 C15 C14 0.0(2) . . . . ?
C9 C10 C15 C14 -177.65(15) . . . . ?
C19 N1 C16 N2 0.5(2) . . . . ?
C19 N1 C16 C8 178.87(14) . . . . ?
C17 N2 C16 N1 -1.8(2) . . . . ?
C17 N2 C16 C8 179.88(14) . . . . ?
O2 C8 C16 N1 173.01(13) . . . . ?
C7 C8 C16 N1 -70.73(18) . . . . ?
C9 C8 C16 N1 51.60(19) . . . . ?
O2 C8 C16 N2 -8.57(19) . . . . ?
C7 C8 C16 N2 107.69(16) . . . . ?
C9 C8 C16 N2 -129.98(15) . . . . ?
C16 N2 C17 C18 -25.3(2) . . . . ?
N2 C17 C18 C19 51.48(18) . . . . ?
C16 N1 C19 C18 27.5(2) . . . . ?
C17 C18 C19 N1 -52.37(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
N2 H2 O2 0.823(15) 2.23(2) 2.6310(18) 110.3(17) .
C19 H19A O1 0.99 2.40 3.141(2) 131.6 4_566
C17 H17A O2 0.99 2.62 3.542(2) 154.8 3_666
C17 H17A O2 0.99 2.62 3.542(2) 154.8 3_666
C19 H19A O1 0.99 2.40 3.141(2) 131.6 4_566
N2 H2 O2 0.823(15) 2.23(2) 2.6310(18) 110.3(17) .

_refine_diff_density_max         0.551
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.053

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_dm15456_0m
_database_code_depnum_ccdc_archive 'CCDC 1404849'
_audit_update_record             
;
2015-06-04 deposited with the CCDC.
2016-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H23 N3 O6'
_chemical_formula_weight         389.40

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                   9.2714(9)
_cell_length_b                   20.4113(19)
_cell_length_c                   9.4269(9)
_cell_angle_alpha                90
_cell_angle_beta                 102.529(2)
_cell_angle_gamma                90
_cell_volume                     1741.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    4075
_cell_measurement_theta_min      4.856
_cell_measurement_theta_max      55.025

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.112
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6716
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12611
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.995
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3424
_reflns_number_gt                2876
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0515P)²+1.7060P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0020(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3424
_refine_ls_number_parameters     269
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1180
_refine_ls_wR_factor_gt          0.1118
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.042
_refine_ls_shift/su_mean         0.005

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.84908(17) 0.22148(8) 0.27503(17) 0.0169(3) Uani 1 1 d . . . . .
N2 N 0.6840(2) 0.33441(9) 0.14230(19) 0.0244(4) Uani 1 1 d . . . . .
N3 N 0.66742(17) 0.36901(7) 0.35992(17) 0.0153(3) Uani 1 1 d . . . . .
O1 O 0.86508(18) 0.30371(7) 0.85813(16) 0.0308(4) Uani 1 1 d . . . . .
H1 H 0.9183 0.2700 0.8714 0.046 Uiso 1 1 calc R U . . .
O2 O 0.92776(15) 0.17498(6) 0.34042(15) 0.0207(3) Uani 1 1 d . . . . .
O3 O 0.83039(15) 0.22576(7) 0.13773(14) 0.0213(3) Uani 1 1 d . . . . .
O4 O 0.51289(14) 0.31151(6) 0.47275(14) 0.0170(3) Uani 1 1 d . . . . .
H4 H 0.4709 0.3120 0.5432 0.026 Uiso 1 1 calc R U . . .
O5 O 1.01752(15) 0.35739(7) 0.58461(17) 0.0292(4) Uani 1 1 d . . . . .
O6 O 0.2747(2) 0.43461(8) 0.6856(2) 0.0387(4) Uani 1 1 d D . . . .
C1 C 0.7348(2) 0.20256(9) 0.5763(2) 0.0168(4) Uani 1 1 d . . . . .
C2 C 0.6957(2) 0.14005(9) 0.5244(2) 0.0192(4) Uani 1 1 d . . . . .
H2A H 0.7140 0.1260 0.4338 0.023 Uiso 1 1 calc R U . . .
C3 C 0.6292(2) 0.09844(10) 0.6080(2) 0.0225(4) Uani 1 1 d . . . . .
H3A H 0.6008 0.0556 0.5733 0.027 Uiso 1 1 calc R U . . .
C4 C 0.6036(2) 0.11826(10) 0.7413(2) 0.0231(4) Uani 1 1 d . . . . .
H4A H 0.5601 0.0887 0.7977 0.028 Uiso 1 1 calc R U . . .
C5 C 0.6410(2) 0.18100(9) 0.7924(2) 0.0202(4) Uani 1 1 d . . . . .
H5 H 0.6234 0.1950 0.8832 0.024 Uiso 1 1 calc R U . . .
C6 C 0.7047(2) 0.22269(9) 0.7076(2) 0.0175(4) Uani 1 1 d . . . . .
C7 C 0.7450(2) 0.29342(9) 0.7394(2) 0.0189(4) Uani 1 1 d . . . . .
H7 H 0.6567 0.3169 0.7589 0.023 Uiso 1 1 calc R U . . .
C8 C 0.77600(19) 0.31896(9) 0.5922(2) 0.0150(4) Uani 1 1 d . . . . .
C9 C 0.8152(2) 0.25694(9) 0.5141(2) 0.0159(4) Uani 1 1 d . . . . .
H9 H 0.9235 0.2491 0.5497 0.019 Uiso 1 1 calc R U . . .
C10 C 0.7879(2) 0.26491(9) 0.3527(2) 0.0156(4) Uani 1 1 d . . . . .
C11 C 0.7152(2) 0.32048(9) 0.2828(2) 0.0164(4) Uani 1 1 d . . . . .
C12 C 0.6120(3) 0.39841(10) 0.1125(2) 0.0279(5) Uani 1 1 d . . . . .
H12 H 0.5220 0.3944 0.0324 0.033 Uiso 1 1 calc R U . . .
C13 C 0.5673(2) 0.41197(10) 0.2568(2) 0.0214(4) Uani 1 1 d . . . . .
H13A H 0.5827 0.4586 0.2850 0.026 Uiso 1 1 calc R U . . .
H13B H 0.4626 0.4003 0.2513 0.026 Uiso 1 1 calc R U . . .
C14 C 0.63620(19) 0.35380(9) 0.50190(19) 0.0150(4) Uani 1 1 d . . . . .
C15 C 0.6024(2) 0.41679(9) 0.5748(2) 0.0175(4) Uani 1 1 d . . . . .
H15A H 0.5754 0.4058 0.6680 0.021 Uiso 1 1 calc R U . . .
H15B H 0.5161 0.4384 0.5119 0.021 Uiso 1 1 calc R U . . .
C16 C 0.7319(2) 0.46454(9) 0.6039(2) 0.0213(4) Uani 1 1 d . . . . .
H16A H 0.7070 0.5026 0.6591 0.026 Uiso 1 1 calc R U . . .
H16B H 0.7498 0.4808 0.5103 0.026 Uiso 1 1 calc R U . . .
C17 C 0.8724(2) 0.43184(9) 0.6900(2) 0.0204(4) Uani 1 1 d . . . . .
H17A H 0.9573 0.4618 0.6952 0.024 Uiso 1 1 calc R U . . .
H17B H 0.8613 0.4231 0.7904 0.024 Uiso 1 1 calc R U . . .
C18 C 0.9022(2) 0.36870(9) 0.6201(2) 0.0176(4) Uani 1 1 d . . . . .
C19 C 0.7158(3) 0.44799(12) 0.0728(3) 0.0406(6) Uani 1 1 d . . . . .
H19A H 0.7982 0.4553 0.1560 0.061 Uiso 1 1 calc R U . . .
H19B H 0.6630 0.4893 0.0462 0.061 Uiso 1 1 calc R U . . .
H19C H 0.7540 0.4318 -0.0098 0.061 Uiso 1 1 calc R U . . .
H2 H 0.725(3) 0.3131(14) 0.083(3) 0.046(8) Uiso 1 1 d . . . . .
H6A H 0.194(3) 0.412(2) 0.641(4) 0.111(15) Uiso 1 1 d D . . . .
H6B H 0.343(6) 0.406(3) 0.722(8) 0.25(3) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 O3 1.271(2) . ?
N1 O2 1.272(2) . ?
N1 C10 1.350(2) . ?
N2 C11 1.324(3) . ?
N2 C12 1.466(3) . ?
N2 H2 0.86(3) . ?
N3 C11 1.359(2) . ?
N3 C14 1.463(2) . ?
N3 C13 1.478(2) . ?
O1 C7 1.413(2) . ?
O1 H1 0.8400 . ?
O4 C14 1.411(2) . ?
O4 H4 0.8400 . ?
O5 C18 1.210(2) . ?
O6 H6A 0.897(19) . ?
O6 H6B 0.88(2) . ?
C1 C2 1.386(3) . ?
C1 C6 1.389(3) . ?
C1 C9 1.524(3) . ?
C2 C3 1.391(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.388(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.386(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.384(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.505(3) . ?
C7 C8 1.566(2) . ?
C7 H7 1.0000 . ?
C8 C18 1.528(3) . ?
C8 C9 1.547(2) . ?
C8 C14 1.559(2) . ?
C9 C10 1.496(3) . ?
C9 H9 1.0000 . ?
C10 C11 1.408(3) . ?
C12 C19 1.498(3) . ?
C12 C13 1.531(3) . ?
C12 H12 1.0000 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.522(2) . ?
C15 C16 1.525(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.530(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.500(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
O3 N1 O2 118.81(15) . . ?
O3 N1 C10 121.77(15) . . ?
O2 N1 C10 119.41(15) . . ?
C11 N2 C12 112.03(17) . . ?
C11 N2 H2 120.7(19) . . ?
C12 N2 H2 124.9(19) . . ?
C11 N3 C14 119.17(15) . . ?
C11 N3 C13 108.17(15) . . ?
C14 N3 C13 120.47(14) . . ?
C7 O1 H1 109.5 . . ?
C14 O4 H4 109.5 . . ?
H6A O6 H6B 107(5) . . ?
C2 C1 C6 119.96(17) . . ?
C2 C1 C9 130.31(17) . . ?
C6 C1 C9 109.69(16) . . ?
C1 C2 C3 118.42(18) . . ?
C1 C2 H2A 120.8 . . ?
C3 C2 H2A 120.8 . . ?
C4 C3 C2 121.27(18) . . ?
C4 C3 H3A 119.4 . . ?
C2 C3 H3A 119.4 . . ?
C5 C4 C3 120.30(18) . . ?
C5 C4 H4A 119.8 . . ?
C3 C4 H4A 119.8 . . ?
C6 C5 C4 118.28(18) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
C5 C6 C1 121.72(18) . . ?
C5 C6 C7 126.43(17) . . ?
C1 C6 C7 111.82(16) . . ?
O1 C7 C6 114.79(15) . . ?
O1 C7 C8 112.85(16) . . ?
C6 C7 C8 103.21(14) . . ?
O1 C7 H7 108.6 . . ?
C6 C7 H7 108.6 . . ?
C8 C7 H7 108.6 . . ?
C18 C8 C9 112.05(15) . . ?
C18 C8 C14 107.79(14) . . ?
C9 C8 C14 111.54(15) . . ?
C18 C8 C7 110.44(15) . . ?
C9 C8 C7 104.85(14) . . ?
C14 C8 C7 110.18(14) . . ?
C10 C9 C1 118.77(15) . . ?
C10 C9 C8 112.91(15) . . ?
C1 C9 C8 103.18(14) . . ?
C10 C9 H9 107.1 . . ?
C1 C9 H9 107.1 . . ?
C8 C9 H9 107.1 . . ?
N1 C10 C11 119.30(16) . . ?
N1 C10 C9 118.81(16) . . ?
C11 C10 C9 121.47(16) . . ?
N2 C11 N3 110.67(16) . . ?
N2 C11 C10 128.32(17) . . ?
N3 C11 C10 121.00(17) . . ?
N2 C12 C19 111.09(19) . . ?
N2 C12 C13 100.96(16) . . ?
C19 C12 C13 114.33(19) . . ?
N2 C12 H12 110.0 . . ?
C19 C12 H12 110.0 . . ?
C13 C12 H12 110.0 . . ?
N3 C13 C12 102.99(15) . . ?
N3 C13 H13A 111.2 . . ?
C12 C13 H13A 111.2 . . ?
N3 C13 H13B 111.2 . . ?
C12 C13 H13B 111.2 . . ?
H13A C13 H13B 109.1 . . ?
O4 C14 N3 105.33(14) . . ?
O4 C14 C15 111.53(14) . . ?
N3 C14 C15 109.56(14) . . ?
O4 C14 C8 111.69(14) . . ?
N3 C14 C8 106.87(14) . . ?
C15 C14 C8 111.55(15) . . ?
C14 C15 C16 112.93(15) . . ?
C14 C15 H15A 109.0 . . ?
C16 C15 H15A 109.0 . . ?
C14 C15 H15B 109.0 . . ?
C16 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C15 C16 C17 111.31(16) . . ?
C15 C16 H16A 109.4 . . ?
C17 C16 H16A 109.4 . . ?
C15 C16 H16B 109.4 . . ?
C17 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
C18 C17 C16 110.97(16) . . ?
C18 C17 H17A 109.4 . . ?
C16 C17 H17A 109.4 . . ?
C18 C17 H17B 109.4 . . ?
C16 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
O5 C18 C17 122.89(17) . . ?
O5 C18 C8 121.01(17) . . ?
C17 C18 C8 116.08(15) . . ?
C12 C19 H19A 109.5 . . ?
C12 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C12 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
C6 C1 C2 C3 -1.2(3) . . . . ?
C9 C1 C2 C3 176.35(18) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C2 C3 C4 C5 1.5(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C1 -1.7(3) . . . . ?
C4 C5 C6 C7 176.27(18) . . . . ?
C2 C1 C6 C5 2.5(3) . . . . ?
C9 C1 C6 C5 -175.55(17) . . . . ?
C2 C1 C6 C7 -175.75(17) . . . . ?
C9 C1 C6 C7 6.2(2) . . . . ?
C5 C6 C7 O1 69.7(3) . . . . ?
C1 C6 C7 O1 -112.18(19) . . . . ?
C5 C6 C7 C8 -167.11(18) . . . . ?
C1 C6 C7 C8 11.0(2) . . . . ?
O1 C7 C8 C18 -19.7(2) . . . . ?
C6 C7 C8 C18 -144.20(15) . . . . ?
O1 C7 C8 C9 101.18(17) . . . . ?
C6 C7 C8 C9 -23.31(18) . . . . ?
O1 C7 C8 C14 -138.67(16) . . . . ?
C6 C7 C8 C14 96.84(16) . . . . ?
C2 C1 C9 C10 35.5(3) . . . . ?
C6 C1 C9 C10 -146.68(16) . . . . ?
C2 C1 C9 C8 161.32(19) . . . . ?
C6 C1 C9 C8 -20.89(19) . . . . ?
C18 C8 C9 C10 -84.01(19) . . . . ?
C14 C8 C9 C10 36.9(2) . . . . ?
C7 C8 C9 C10 156.17(15) . . . . ?
C18 C8 C9 C1 146.52(15) . . . . ?
C14 C8 C9 C1 -92.53(16) . . . . ?
C7 C8 C9 C1 26.70(18) . . . . ?
O3 N1 C10 C11 -7.1(3) . . . . ?
O2 N1 C10 C11 172.77(16) . . . . ?
O3 N1 C10 C9 -179.76(15) . . . . ?
O2 N1 C10 C9 0.1(2) . . . . ?
C1 C9 C10 N1 -74.6(2) . . . . ?
C8 C9 C10 N1 164.40(15) . . . . ?
C1 C9 C10 C11 112.90(19) . . . . ?
C8 C9 C10 C11 -8.1(2) . . . . ?
C12 N2 C11 N3 1.8(2) . . . . ?
C12 N2 C11 C10 -177.78(19) . . . . ?
C14 N3 C11 N2 155.80(16) . . . . ?
C13 N3 C11 N2 13.2(2) . . . . ?
C14 N3 C11 C10 -24.6(3) . . . . ?
C13 N3 C11 C10 -167.15(17) . . . . ?
N1 C10 C11 N2 7.3(3) . . . . ?
C9 C10 C11 N2 179.70(18) . . . . ?
N1 C10 C11 N3 -172.31(16) . . . . ?
C9 C10 C11 N3 0.1(3) . . . . ?
C11 N2 C12 C19 106.6(2) . . . . ?
C11 N2 C12 C13 -15.0(2) . . . . ?
C11 N3 C13 C12 -21.7(2) . . . . ?
C14 N3 C13 C12 -163.74(16) . . . . ?
N2 C12 C13 N3 21.1(2) . . . . ?
C19 C12 C13 N3 -98.2(2) . . . . ?
C11 N3 C14 O4 -66.59(19) . . . . ?
C13 N3 C14 O4 71.36(19) . . . . ?
C11 N3 C14 C15 173.32(16) . . . . ?
C13 N3 C14 C15 -48.7(2) . . . . ?
C11 N3 C14 C8 52.3(2) . . . . ?
C13 N3 C14 C8 -169.72(15) . . . . ?
C18 C8 C14 O4 -179.12(14) . . . . ?
C9 C8 C14 O4 57.47(19) . . . . ?
C7 C8 C14 O4 -58.55(19) . . . . ?
C18 C8 C14 N3 66.18(17) . . . . ?
C9 C8 C14 N3 -57.23(18) . . . . ?
C7 C8 C14 N3 -173.25(14) . . . . ?
C18 C8 C14 C15 -53.55(19) . . . . ?
C9 C8 C14 C15 -176.96(14) . . . . ?
C7 C8 C14 C15 67.02(18) . . . . ?
O4 C14 C15 C16 -178.33(15) . . . . ?
N3 C14 C15 C16 -62.1(2) . . . . ?
C8 C14 C15 C16 56.0(2) . . . . ?
C14 C15 C16 C17 -53.9(2) . . . . ?
C15 C16 C17 C18 51.2(2) . . . . ?
C16 C17 C18 O5 124.5(2) . . . . ?
C16 C17 C18 C8 -54.2(2) . . . . ?
C9 C8 C18 O5 -1.1(3) . . . . ?
C14 C8 C18 O5 -124.19(19) . . . . ?
C7 C8 C18 O5 115.4(2) . . . . ?
C9 C8 C18 C17 177.60(15) . . . . ?
C14 C8 C18 C17 54.5(2) . . . . ?
C7 C8 C18 C17 -65.9(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O4 0.84 2.02 2.8167(19) 157.7 4_666
O4 H4 O3 0.84 1.89 2.6462(17) 148.3 4_566
C7 H7 O2 1.00 2.41 3.345(2) 154.5 4_566
C12 H12 O2 1.00 2.31 3.137(3) 138.7 4_565
C13 H13A O6 0.99 2.53 3.450(3) 153.9 3_666
C17 H17B O1 0.99 2.52 3.066(2) 114.7 .
O6 H6A O5 0.897(19) 1.96(2) 2.845(2) 168(4) 1_455
O6 H6B N1 0.88(2) 2.64(6) 3.329(2) 136(6) 4_566
O6 H6B O2 0.88(2) 2.05(4) 2.872(2) 156(7) 4_566
N2 H2 O3 0.86(3) 2.04(3) 2.605(2) 122(2) .
O1 H1 O4 0.84 2.02 2.8167(19) 157.7 4_666
O4 H4 O3 0.84 1.89 2.6462(17) 148.3 4_566
C7 H7 O2 1.00 2.41 3.345(2) 154.5 4_566
C12 H12 O2 1.00 2.31 3.137(3) 138.7 4_565
C13 H13A O6 0.99 2.53 3.450(3) 153.9 3_666
C17 H17B O1 0.99 2.52 3.066(2) 114.7 .
O6 H6A O5 0.897(19) 1.96(2) 2.845(2) 168(4) 1_455
O6 H6B N1 0.88(2) 2.64(6) 3.329(2) 136(6) 4_566
O6 H6B O2 0.88(2) 2.05(4) 2.872(2) 156(7) 4_566

_refine_diff_density_max         0.688
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.052

_shelxl_version_number           2013-4

