# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_wmj18159
_database_code_depnum_ccdc_archive 'CCDC 1866987'
loop_
_audit_author_name
_audit_author_address
'Haijun Chen'
;Fuzhou University,
China
;
_audit_update_record             
;
2018-09-11 deposited with the CCDC.	2019-09-24 downloaded from the CCDC.
;
_audit_creation_date             2018-09-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H17 N3 O3'
_chemical_formula_sum            'C19 H17 N3 O3'
_chemical_formula_weight         335.35
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0148 0.0070 '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 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   15.3447(4)
_cell_length_b                   10.1160(2)
_cell_length_c                   10.7205(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.8920(10)
_cell_angle_gamma                90
_cell_volume                     1564.82(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7562
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.85
_cell_measurement_theta_min      4.646
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.517
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1870 before and 0.0850 after correction. The Ratio of minimum to maximum transmission is 0.7060. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0701
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16321
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.912
_diffrn_reflns_theta_min         4.644
_diffrn_ambient_temperature      169.97
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2364
_reflns_number_total             2963
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         2963
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0447
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0463P)²+0.8343P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1137
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C16(H16), C17(H17), C18(H18), C19(H19)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.40900(9) -0.64083(13) -0.66283(13) 0.0330(3) Uani 1 1 d . . . . .
O2 O -0.26077(9) -0.77523(12) -0.52472(13) 0.0299(3) Uani 1 1 d . . . . .
H2 H -0.314923 -0.773273 -0.579807 0.045 Uiso 1 1 calc GR . . . .
O3 O -0.21832(9) -0.24257(13) -0.70970(13) 0.0289(3) Uani 1 1 d . . . . .
N1 N -0.42652(10) -0.42935(15) -0.61143(14) 0.0222(3) Uani 1 1 d . . . . .
N2 N -0.23362(10) -0.43811(14) -0.61867(14) 0.0210(3) Uani 1 1 d . . . . .
N3 N -0.24307(10) -0.49079(16) -0.39666(14) 0.0208(3) Uani 1 1 d . . . . .
C1 C -0.37380(12) -0.53725(18) -0.60690(16) 0.0222(4) Uani 1 1 d . . . . .
C2 C -0.26915(12) -0.52539(18) -0.53588(16) 0.0206(4) Uani 1 1 d . . . . .
C3 C -0.21381(12) -0.65791(17) -0.53527(17) 0.0224(4) Uani 1 1 d . . . . .
C4 C -0.18810(13) -0.65027(19) -0.66018(17) 0.0272(4) Uani 1 1 d . . . . .
H4A H -0.133012 -0.705318 -0.651584 0.033 Uiso 1 1 calc R . . . .
H4B H -0.240167 -0.679816 -0.738825 0.033 Uiso 1 1 calc R . . . .
C5 C -0.16744(13) -0.50527(19) -0.67059(18) 0.0256(4) Uani 1 1 d . . . . .
H5A H -0.102628 -0.484100 -0.616241 0.031 Uiso 1 1 calc R . . . .
H5B H -0.178194 -0.479755 -0.763792 0.031 Uiso 1 1 calc R . . . .
C6 C -0.25321(12) -0.30837(18) -0.64233(17) 0.0222(4) Uani 1 1 d . . . . .
C7 C -0.31460(12) -0.24442(18) -0.57710(16) 0.0211(4) Uani 1 1 d . . . . .
C8 C -0.29175(13) -0.11488(19) -0.53304(17) 0.0261(4) Uani 1 1 d . . . . .
H8 H -0.241400 -0.072468 -0.549238 0.031 Uiso 1 1 calc R . . . .
C9 C -0.34064(13) -0.0470(2) -0.46644(18) 0.0294(4) Uani 1 1 d . . . . .
H9 H -0.324372 0.041349 -0.437798 0.035 Uiso 1 1 calc R . . . .
C10 C -0.41355(13) -0.1090(2) -0.44193(18) 0.0295(5) Uani 1 1 d . . . . .
H10 H -0.445836 -0.064248 -0.392968 0.035 Uiso 1 1 calc R . . . .
C11 C -0.43971(13) -0.23534(19) -0.48813(18) 0.0270(4) Uani 1 1 d . . . . .
H11 H -0.491049 -0.276062 -0.473118 0.032 Uiso 1 1 calc R . . . .
C12 C -0.39127(12) -0.30337(18) -0.55657(16) 0.0216(4) Uani 1 1 d . . . . .
C13 C -0.52734(12) -0.4402(2) -0.68070(18) 0.0287(4) Uani 1 1 d . . . . .
H13A H -0.557322 -0.468952 -0.617894 0.043 Uiso 1 1 calc GR . . . .
H13B H -0.539589 -0.504916 -0.752654 0.043 Uiso 1 1 calc GR . . . .
H13C H -0.552115 -0.353907 -0.717583 0.043 Uiso 1 1 calc GR . . . .
C14 C -0.13397(12) -0.64203(17) -0.40725(16) 0.0208(4) Uani 1 1 d . . . . .
C15 C -0.15465(12) -0.54408(17) -0.33135(16) 0.0200(4) Uani 1 1 d . . . . .
C16 C -0.09245(12) -0.51160(18) -0.20720(17) 0.0228(4) Uani 1 1 d . . . . .
H16 H -0.105825 -0.443616 -0.155283 0.027 Uiso 1 1 calc R . . . .
C17 C -0.00998(12) -0.58203(19) -0.16161(18) 0.0263(4) Uani 1 1 d . . . . .
H17 H 0.033858 -0.560916 -0.077221 0.032 Uiso 1 1 calc R . . . .
C18 C 0.01029(13) -0.68224(19) -0.23555(18) 0.0278(4) Uani 1 1 d . . . . .
H18 H 0.066707 -0.730077 -0.201082 0.033 Uiso 1 1 calc R . . . .
C19 C -0.05241(13) -0.71248(19) -0.36057(18) 0.0258(4) Uani 1 1 d . . . . .
H19 H -0.039210 -0.780394 -0.412704 0.031 Uiso 1 1 calc R . . . .
H3 H -0.2543(14) -0.411(2) -0.373(2) 0.029(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.236(2) . ?
O2 H2 0.8400 . ?
O2 C3 1.413(2) . ?
O3 C6 1.231(2) . ?
N1 C1 1.350(2) . ?
N1 C12 1.430(2) . ?
N1 C13 1.475(2) . ?
N2 C2 1.481(2) . ?
N2 C5 1.479(2) . ?
N2 C6 1.351(2) . ?
N3 C2 1.450(2) . ?
N3 C15 1.405(2) . ?
N3 H3 0.88(2) . ?
C1 C2 1.530(2) . ?
C2 C3 1.586(2) . ?
C3 C4 1.521(2) . ?
C3 C14 1.505(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.513(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.498(2) . ?
C7 C8 1.397(3) . ?
C7 C12 1.402(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.382(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.383(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.380(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.391(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.386(2) . ?
C14 C19 1.378(3) . ?
C15 C16 1.388(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.388(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.386(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.392(3) . ?
C19 H19 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
C3 O2 H2 109.5 . . ?
C1 N1 C12 124.58(14) . . ?
C1 N1 C13 118.11(15) . . ?
C12 N1 C13 117.28(14) . . ?
C5 N2 C2 113.05(14) . . ?
C6 N2 C2 126.00(14) . . ?
C6 N2 C5 120.87(14) . . ?
C2 N3 H3 120.6(13) . . ?
C15 N3 C2 107.56(14) . . ?
C15 N3 H3 117.2(13) . . ?
O1 C1 N1 120.69(16) . . ?
O1 C1 C2 121.27(16) . . ?
N1 C1 C2 117.99(15) . . ?
N2 C2 C1 106.65(13) . . ?
N2 C2 C3 101.57(13) . . ?
N3 C2 N2 116.35(14) . . ?
N3 C2 C1 113.98(14) . . ?
N3 C2 C3 103.88(13) . . ?
C1 C2 C3 113.93(14) . . ?
O2 C3 C2 115.06(14) . . ?
O2 C3 C4 113.90(15) . . ?
O2 C3 C14 107.20(14) . . ?
C4 C3 C2 104.62(14) . . ?
C14 C3 C2 100.49(13) . . ?
C14 C3 C4 115.01(15) . . ?
C3 C4 H4A 111.0 . . ?
C3 C4 H4B 111.0 . . ?
H4A C4 H4B 109.0 . . ?
C5 C4 C3 103.75(14) . . ?
C5 C4 H4A 111.0 . . ?
C5 C4 H4B 111.0 . . ?
N2 C5 C4 103.28(14) . . ?
N2 C5 H5A 111.1 . . ?
N2 C5 H5B 111.1 . . ?
C4 C5 H5A 111.1 . . ?
C4 C5 H5B 111.1 . . ?
H5A C5 H5B 109.1 . . ?
O3 C6 N2 121.47(16) . . ?
O3 C6 C7 120.58(16) . . ?
N2 C6 C7 117.85(15) . . ?
C8 C7 C6 115.96(16) . . ?
C8 C7 C12 118.28(16) . . ?
C12 C7 C6 125.76(16) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 C7 121.56(18) . . ?
C9 C8 H8 119.2 . . ?
C8 C9 H9 120.4 . . ?
C8 C9 C10 119.28(18) . . ?
C10 C9 H9 120.4 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.46(18) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.33(18) . . ?
C12 C11 H11 119.8 . . ?
C7 C12 N1 122.32(16) . . ?
C11 C12 N1 117.54(16) . . ?
C11 C12 C7 120.00(17) . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C3 109.49(15) . . ?
C19 C14 C3 129.26(16) . . ?
C19 C14 C15 121.19(16) . . ?
C14 C15 N3 110.91(15) . . ?
C14 C15 C16 120.81(16) . . ?
C16 C15 N3 128.26(16) . . ?
C15 C16 H16 121.2 . . ?
C15 C16 C17 117.59(17) . . ?
C17 C16 H16 121.2 . . ?
C16 C17 H17 119.0 . . ?
C18 C17 C16 121.95(17) . . ?
C18 C17 H17 119.0 . . ?
C17 C18 H18 120.2 . . ?
C17 C18 C19 119.69(17) . . ?
C19 C18 H18 120.2 . . ?
C14 C19 C18 118.74(17) . . ?
C14 C19 H19 120.6 . . ?
C18 C19 H19 120.6 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1 0.84 1.95 2.6311(19) 137.7 .

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_dd18254
_database_code_depnum_ccdc_archive 'CCDC 1880631'
loop_
_audit_author_name
_audit_author_address
'Haijun Chen'
;Fuzhou University,
China
;
_audit_update_record             
;
2018-11-22 deposited with the CCDC.	2019-09-24 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 H17 N3 O3'
_chemical_formula_weight         335.35

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                   16.6547(7)
_cell_length_b                   13.5081(6)
_cell_length_c                   16.2182(7)
_cell_angle_alpha                90
_cell_angle_beta                 117.9680(10)
_cell_angle_gamma                90
_cell_volume                     3222.5(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4745
_cell_measurement_theta_min      5.539
_cell_measurement_theta_max      54.757

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_F_000             1408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6659
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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            31796
_diffrn_reflns_av_unetI/netI     0.0582
_diffrn_reflns_av_R_equivalents  0.0645
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.512
_diffrn_reflns_theta_max         26.000
_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             6314
_reflns_number_gt                3563
_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)+(0.0541P)²+0.7746P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0075(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6314
_refine_ls_number_parameters     454
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1184
_refine_ls_R_factor_gt           0.0545
_refine_ls_wR_factor_ref         0.1468
_refine_ls_wR_factor_gt          0.1119
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_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 0.75141(15) -0.04657(17) 0.83231(15) 0.0842(7) Uani 1 1 d . . . . .
O2 O 0.62755(11) 0.07260(12) 0.65643(11) 0.0455(4) Uani 1 1 d . . . . .
O3 O 0.53277(14) 0.30749(14) 0.75761(14) 0.0652(6) Uani 1 1 d . . . . .
N1 N 0.83624(16) -0.02775(17) 0.75554(16) 0.0598(6) Uani 1 1 d . . . . .
H1 H 0.8731 -0.0765 0.7803 0.072 Uiso 1 1 calc R U . . .
N2 N 0.57501(15) 0.14971(17) 0.75305(15) 0.0533(6) Uani 1 1 d . . . . .
N3 N 0.48047(14) 0.03942(15) 0.63097(14) 0.0475(5) Uani 1 1 d . . . . .
C1 C 0.83800(18) 0.03530(19) 0.68780(18) 0.0496(7) Uani 1 1 d . . . . .
C2 C 0.89328(19) 0.0312(2) 0.6464(2) 0.0629(8) Uani 1 1 d . . . . .
H2 H 0.9383 -0.0167 0.6633 0.075 Uiso 1 1 calc R U . . .
C3 C 0.8796(2) 0.1009(3) 0.5787(2) 0.0734(9) Uani 1 1 d . . . . .
H3 H 0.9154 0.0990 0.5488 0.088 Uiso 1 1 calc R U . . .
C4 C 0.8141(2) 0.1728(3) 0.5546(2) 0.0760(10) Uani 1 1 d . . . . .
H4 H 0.8065 0.2195 0.5093 0.091 Uiso 1 1 calc R U . . .
C5 C 0.75934(19) 0.1761(2) 0.5977(2) 0.0653(8) Uani 1 1 d . . . . .
H5 H 0.7149 0.2246 0.5815 0.078 Uiso 1 1 calc R U . . .
C6 C 0.77126(17) 0.10695(19) 0.66452(18) 0.0491(7) Uani 1 1 d . . . . .
C7 C 0.72209(17) 0.09131(19) 0.72086(18) 0.0502(7) Uani 1 1 d . . . . .
C8 C 0.76976(19) -0.0029(2) 0.7773(2) 0.0597(8) Uani 1 1 d . . . . .
C9 C 0.73020(19) 0.1784(2) 0.7844(2) 0.0630(8) Uani 1 1 d . . . . .
H9A H 0.7925 0.1831 0.8337 0.076 Uiso 1 1 calc R U . . .
H9B H 0.7158 0.2393 0.7485 0.076 Uiso 1 1 calc R U . . .
C10 C 0.66729(19) 0.1678(3) 0.8276(2) 0.0699(9) Uani 1 1 d . . . . .
H10A H 0.6870 0.1130 0.8714 0.084 Uiso 1 1 calc R U . . .
H10B H 0.6686 0.2277 0.8611 0.084 Uiso 1 1 calc R U . . .
C11 C 0.56975(17) 0.06158(19) 0.70134(17) 0.0480(7) Uani 1 1 d . . . . .
H11 H 0.5922 0.0057 0.7449 0.058 Uiso 1 1 calc R U . . .
C12 C 0.51507(19) 0.2253(2) 0.71910(19) 0.0490(7) Uani 1 1 d . . . . .
C13 C 0.42831(18) 0.20348(18) 0.63721(17) 0.0442(6) Uani 1 1 d . . . . .
C14 C 0.3603(2) 0.2749(2) 0.6035(2) 0.0554(7) Uani 1 1 d . . . . .
H14 H 0.3710 0.3363 0.6328 0.066 Uiso 1 1 calc R U . . .
C15 C 0.2779(2) 0.2563(2) 0.5281(2) 0.0651(8) Uani 1 1 d . . . . .
H15 H 0.2326 0.3043 0.5058 0.078 Uiso 1 1 calc R U . . .
C16 C 0.2633(2) 0.1649(3) 0.4859(2) 0.0675(8) Uani 1 1 d . . . . .
H16 H 0.2074 0.1518 0.4345 0.081 Uiso 1 1 calc R U . . .
C17 C 0.32904(19) 0.0925(2) 0.51744(19) 0.0586(8) Uani 1 1 d . . . . .
H17 H 0.3173 0.0316 0.4873 0.070 Uiso 1 1 calc R U . . .
C18 C 0.41382(17) 0.11044(19) 0.59499(17) 0.0443(6) Uani 1 1 d . . . . .
C19 C 0.4676(2) -0.05864(18) 0.58896(19) 0.0585(8) Uani 1 1 d . . . . .
H19A H 0.4573 -0.0525 0.5258 0.088 Uiso 1 1 calc R U . . .
H19B H 0.4161 -0.0900 0.5894 0.088 Uiso 1 1 calc R U . . .
H19C H 0.5210 -0.0980 0.6240 0.088 Uiso 1 1 calc R U . . .
O4 O 0.75794(16) 0.43901(17) 0.80110(16) 0.0858(7) Uani 1 1 d . . . . .
O5 O 0.75588(11) 0.57722(12) 0.65130(11) 0.0488(5) Uani 1 1 d . . . . .
O6 O 0.95000(13) 0.79766(14) 0.80373(14) 0.0639(5) Uani 1 1 d . . . . .
N4 N 0.60612(17) 0.46857(17) 0.70673(17) 0.0618(7) Uani 1 1 d . . . . .
H4A H 0.5846 0.4186 0.7228 0.074 Uiso 1 1 calc R U . . .
N5 N 0.89083(14) 0.64296(17) 0.77340(15) 0.0530(6) Uani 1 1 d . . . . .
N6 N 0.89309(15) 0.54465(18) 0.65227(16) 0.0631(7) Uani 1 1 d . . . . .
C20 C 0.55205(19) 0.53797(19) 0.63837(19) 0.0503(7) Uani 1 1 d . . . . .
C21 C 0.4598(2) 0.5362(2) 0.5806(2) 0.0608(8) Uani 1 1 d . . . . .
H21 H 0.4234 0.4861 0.5845 0.073 Uiso 1 1 calc R U . . .
C22 C 0.4231(2) 0.6125(2) 0.5164(2) 0.0633(8) Uani 1 1 d . . . . .
H22 H 0.3610 0.6130 0.4757 0.076 Uiso 1 1 calc R U . . .
C23 C 0.4768(2) 0.6876(2) 0.5115(2) 0.0600(8) Uani 1 1 d . . . . .
H23 H 0.4505 0.7388 0.4688 0.072 Uiso 1 1 calc R U . . .
C24 C 0.56971(19) 0.6870(2) 0.5701(2) 0.0536(7) Uani 1 1 d . . . . .
H24 H 0.6061 0.7375 0.5669 0.064 Uiso 1 1 calc R U . . .
C25 C 0.60758(18) 0.61115(19) 0.63287(18) 0.0465(6) Uani 1 1 d . . . . .
C26 C 0.70417(18) 0.58979(19) 0.70155(18) 0.0494(7) Uani 1 1 d . . . . .
C27 C 0.6957(2) 0.4896(2) 0.7442(2) 0.0614(8) Uani 1 1 d . . . . .
C28 C 0.74818(19) 0.6689(2) 0.7766(2) 0.0592(8) Uani 1 1 d . . . . .
H28A H 0.7372 0.7334 0.7470 0.071 Uiso 1 1 calc R U . . .
H28B H 0.7197 0.6681 0.8169 0.071 Uiso 1 1 calc R U . . .
C29 C 0.84940(19) 0.6543(2) 0.83553(19) 0.0623(8) Uani 1 1 d . . . . .
H29A H 0.8757 0.7110 0.8762 0.075 Uiso 1 1 calc R U . . .
H29B H 0.8611 0.5958 0.8741 0.075 Uiso 1 1 calc R U . . .
C30 C 0.85164(18) 0.5609(2) 0.71066(19) 0.0537(7) Uani 1 1 d . . . . .
H30 H 0.8591 0.5011 0.7477 0.064 Uiso 1 1 calc R U . . .
C31 C 0.93333(17) 0.7202(2) 0.75767(19) 0.0508(7) Uani 1 1 d . . . . .
C32 C 0.96045(18) 0.7060(2) 0.68449(19) 0.0542(7) Uani 1 1 d . . . . .
C33 C 1.0097(2) 0.7792(2) 0.6683(2) 0.0690(9) Uani 1 1 d . . . . .
H33 H 1.0265 0.8359 0.7051 0.083 Uiso 1 1 calc R U . . .
C34 C 1.0342(2) 0.7695(3) 0.5990(3) 0.0885(12) Uani 1 1 d . . . . .
H34 H 1.0683 0.8185 0.5895 0.106 Uiso 1 1 calc R U . . .
C35 C 1.0078(2) 0.6872(4) 0.5441(2) 0.0877(12) Uani 1 1 d . . . . .
H35 H 1.0224 0.6818 0.4956 0.105 Uiso 1 1 calc R U . . .
C36 C 0.9601(2) 0.6117(3) 0.5585(2) 0.0771(10) Uani 1 1 d . . . . .
H36 H 0.9434 0.5559 0.5205 0.093 Uiso 1 1 calc R U . . .
C37 C 0.93675(18) 0.6200(2) 0.63174(19) 0.0581(8) Uani 1 1 d . . . . .
C38 C 0.8624(2) 0.4542(2) 0.5955(2) 0.0877(11) Uani 1 1 d . . . . .
H38A H 0.8352 0.4102 0.6218 0.132 Uiso 1 1 calc R U . . .
H38B H 0.9134 0.4221 0.5946 0.132 Uiso 1 1 calc R U . . .
H38C H 0.8184 0.4711 0.5329 0.132 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 C8 1.221(3) . ?
O2 C7 1.446(3) . ?
O2 C11 1.462(3) . ?
O3 C12 1.239(3) . ?
N1 C8 1.353(3) . ?
N1 C1 1.401(3) . ?
N1 H1 0.8600 . ?
N2 C12 1.352(3) . ?
N2 C11 1.435(3) . ?
N2 C10 1.463(3) . ?
N3 C18 1.373(3) . ?
N3 C11 1.418(3) . ?
N3 C19 1.459(3) . ?
C1 C2 1.372(4) . ?
C1 C6 1.386(3) . ?
C2 C3 1.381(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.372(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.501(4) . ?
C7 C9 1.528(4) . ?
C7 C8 1.551(4) . ?
C9 C10 1.516(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11 0.9800 . ?
C12 C13 1.463(4) . ?
C13 C14 1.390(4) . ?
C13 C18 1.397(3) . ?
C14 C15 1.367(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.376(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.375(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.403(4) . ?
C17 H17 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
O4 C27 1.224(3) . ?
O5 C30 1.442(3) . ?
O5 C26 1.447(3) . ?
O6 C31 1.239(3) . ?
N4 C27 1.350(4) . ?
N4 C20 1.408(3) . ?
N4 H4A 0.8600 . ?
N5 C31 1.350(3) . ?
N5 C30 1.437(3) . ?
N5 C29 1.472(3) . ?
N6 C37 1.379(4) . ?
N6 C30 1.427(3) . ?
N6 C38 1.470(3) . ?
C20 C21 1.375(4) . ?
C20 C25 1.385(3) . ?
C21 C22 1.387(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.378(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.385(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.372(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.494(4) . ?
C26 C28 1.525(4) . ?
C26 C27 1.556(4) . ?
C28 C29 1.511(4) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 H30 0.9800 . ?
C31 C32 1.467(4) . ?
C32 C37 1.386(4) . ?
C32 C33 1.387(4) . ?
C33 C34 1.369(4) . ?
C33 H33 0.9300 . ?
C34 C35 1.362(5) . ?
C34 H34 0.9300 . ?
C35 C36 1.378(5) . ?
C35 H35 0.9300 . ?
C36 C37 1.417(4) . ?
C36 H36 0.9300 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?

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
C7 O2 C11 113.96(18) . . ?
C8 N1 C1 112.0(2) . . ?
C8 N1 H1 124.0 . . ?
C1 N1 H1 124.0 . . ?
C12 N2 C11 123.9(2) . . ?
C12 N2 C10 120.0(2) . . ?
C11 N2 C10 111.9(2) . . ?
C18 N3 C11 121.9(2) . . ?
C18 N3 C19 121.6(2) . . ?
C11 N3 C19 115.9(2) . . ?
C2 C1 C6 122.1(3) . . ?
C2 C1 N1 128.7(3) . . ?
C6 C1 N1 109.2(2) . . ?
C1 C2 C3 117.6(3) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 H2 121.2 . . ?
C4 C3 C2 121.4(3) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 119.4(3) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C1 119.4(3) . . ?
C5 C6 C7 131.2(2) . . ?
C1 C6 C7 109.4(2) . . ?
O2 C7 C6 107.7(2) . . ?
O2 C7 C9 110.1(2) . . ?
C6 C7 C9 113.7(2) . . ?
O2 C7 C8 111.4(2) . . ?
C6 C7 C8 101.6(2) . . ?
C9 C7 C8 112.0(2) . . ?
O1 C8 N1 125.9(3) . . ?
O1 C8 C7 126.4(3) . . ?
N1 C8 C7 107.7(2) . . ?
C10 C9 C7 112.1(2) . . ?
C10 C9 H9A 109.2 . . ?
C7 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C7 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
N2 C10 C9 108.7(2) . . ?
N2 C10 H10A 110.0 . . ?
C9 C10 H10A 110.0 . . ?
N2 C10 H10B 110.0 . . ?
C9 C10 H10B 110.0 . . ?
H10A C10 H10B 108.3 . . ?
N3 C11 N2 113.5(2) . . ?
N3 C11 O2 107.91(19) . . ?
N2 C11 O2 109.43(19) . . ?
N3 C11 H11 108.6 . . ?
N2 C11 H11 108.6 . . ?
O2 C11 H11 108.6 . . ?
O3 C12 N2 121.0(3) . . ?
O3 C12 C13 122.6(3) . . ?
N2 C12 C13 116.3(2) . . ?
C14 C13 C18 120.7(3) . . ?
C14 C13 C12 119.5(2) . . ?
C18 C13 C12 119.8(2) . . ?
C15 C14 C13 121.0(3) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 118.6(3) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
C17 C16 C15 121.9(3) . . ?
C17 C16 H16 119.0 . . ?
C15 C16 H16 119.0 . . ?
C16 C17 C18 120.1(3) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
N3 C18 C13 120.1(2) . . ?
N3 C18 C17 122.2(2) . . ?
C13 C18 C17 117.7(2) . . ?
N3 C19 H19A 109.5 . . ?
N3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C30 O5 C26 113.96(19) . . ?
C27 N4 C20 112.2(2) . . ?
C27 N4 H4A 123.9 . . ?
C20 N4 H4A 123.9 . . ?
C31 N5 C30 124.5(2) . . ?
C31 N5 C29 120.3(2) . . ?
C30 N5 C29 111.2(2) . . ?
C37 N6 C30 121.4(2) . . ?
C37 N6 C38 122.0(2) . . ?
C30 N6 C38 114.2(2) . . ?
C21 C20 C25 122.4(3) . . ?
C21 C20 N4 128.5(3) . . ?
C25 C20 N4 109.0(2) . . ?
C20 C21 C22 117.2(3) . . ?
C20 C21 H21 121.4 . . ?
C22 C21 H21 121.4 . . ?
C23 C22 C21 121.4(3) . . ?
C23 C22 H22 119.3 . . ?
C21 C22 H22 119.3 . . ?
C22 C23 C24 120.1(3) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C25 C24 C23 119.4(3) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C24 C25 C20 119.5(3) . . ?
C24 C25 C26 131.1(2) . . ?
C20 C25 C26 109.4(2) . . ?
O5 C26 C25 108.7(2) . . ?
O5 C26 C28 110.0(2) . . ?
C25 C26 C28 114.0(2) . . ?
O5 C26 C27 110.5(2) . . ?
C25 C26 C27 102.0(2) . . ?
C28 C26 C27 111.4(2) . . ?
O4 C27 N4 126.0(3) . . ?
O4 C27 C26 126.8(3) . . ?
N4 C27 C26 107.1(3) . . ?
C29 C28 C26 112.9(2) . . ?
C29 C28 H28A 109.0 . . ?
C26 C28 H28A 109.0 . . ?
C29 C28 H28B 109.0 . . ?
C26 C28 H28B 109.0 . . ?
H28A C28 H28B 107.8 . . ?
N5 C29 C28 108.8(2) . . ?
N5 C29 H29A 109.9 . . ?
C28 C29 H29A 109.9 . . ?
N5 C29 H29B 109.9 . . ?
C28 C29 H29B 109.9 . . ?
H29A C29 H29B 108.3 . . ?
N6 C30 N5 112.9(2) . . ?
N6 C30 O5 108.0(2) . . ?
N5 C30 O5 110.4(2) . . ?
N6 C30 H30 108.5 . . ?
N5 C30 H30 108.5 . . ?
O5 C30 H30 108.5 . . ?
O6 C31 N5 121.8(2) . . ?
O6 C31 C32 122.1(3) . . ?
N5 C31 C32 116.1(2) . . ?
C37 C32 C33 120.2(3) . . ?
C37 C32 C31 120.2(3) . . ?
C33 C32 C31 119.6(3) . . ?
C34 C33 C32 121.1(3) . . ?
C34 C33 H33 119.4 . . ?
C32 C33 H33 119.4 . . ?
C35 C34 C33 119.1(4) . . ?
C35 C34 H34 120.5 . . ?
C33 C34 H34 120.5 . . ?
C34 C35 C36 121.9(3) . . ?
C34 C35 H35 119.1 . . ?
C36 C35 H35 119.1 . . ?
C35 C36 C37 119.3(3) . . ?
C35 C36 H36 120.3 . . ?
C37 C36 H36 120.3 . . ?
N6 C37 C32 119.9(2) . . ?
N6 C37 C36 121.8(3) . . ?
C32 C37 C36 118.2(3) . . ?
N6 C38 H38A 109.5 . . ?
N6 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
N6 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 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
C8 N1 C1 C2 -177.6(3) . . . . ?
C8 N1 C1 C6 1.4(3) . . . . ?
C6 C1 C2 C3 -0.9(4) . . . . ?
N1 C1 C2 C3 178.0(3) . . . . ?
C1 C2 C3 C4 1.1(5) . . . . ?
C2 C3 C4 C5 -0.7(5) . . . . ?
C3 C4 C5 C6 0.1(5) . . . . ?
C4 C5 C6 C1 0.1(4) . . . . ?
C4 C5 C6 C7 -178.9(3) . . . . ?
C2 C1 C6 C5 0.3(4) . . . . ?
N1 C1 C6 C5 -178.8(2) . . . . ?
C2 C1 C6 C7 179.5(2) . . . . ?
N1 C1 C6 C7 0.5(3) . . . . ?
C11 O2 C7 C6 -176.60(19) . . . . ?
C11 O2 C7 C9 -52.1(3) . . . . ?
C11 O2 C7 C8 72.8(3) . . . . ?
C5 C6 C7 O2 60.1(4) . . . . ?
C1 C6 C7 O2 -119.0(2) . . . . ?
C5 C6 C7 C9 -62.2(4) . . . . ?
C1 C6 C7 C9 118.7(3) . . . . ?
C5 C6 C7 C8 177.3(3) . . . . ?
C1 C6 C7 C8 -1.8(3) . . . . ?
C1 N1 C8 O1 178.1(3) . . . . ?
C1 N1 C8 C7 -2.5(3) . . . . ?
O2 C7 C8 O1 -63.5(4) . . . . ?
C6 C7 C8 O1 -178.0(3) . . . . ?
C9 C7 C8 O1 60.3(4) . . . . ?
O2 C7 C8 N1 117.1(2) . . . . ?
C6 C7 C8 N1 2.6(3) . . . . ?
C9 C7 C8 N1 -119.0(2) . . . . ?
O2 C7 C9 C10 49.4(3) . . . . ?
C6 C7 C9 C10 170.3(2) . . . . ?
C8 C7 C9 C10 -75.2(3) . . . . ?
C12 N2 C10 C9 -98.3(3) . . . . ?
C11 N2 C10 C9 59.6(3) . . . . ?
C7 C9 C10 N2 -52.6(3) . . . . ?
C18 N3 C11 N2 21.1(3) . . . . ?
C19 N3 C11 N2 -168.2(2) . . . . ?
C18 N3 C11 O2 -100.3(2) . . . . ?
C19 N3 C11 O2 70.4(3) . . . . ?
C12 N2 C11 N3 -25.6(3) . . . . ?
C10 N2 C11 N3 177.5(2) . . . . ?
C12 N2 C11 O2 95.0(3) . . . . ?
C10 N2 C11 O2 -61.9(3) . . . . ?
C7 O2 C11 N3 -177.49(19) . . . . ?
C7 O2 C11 N2 58.5(3) . . . . ?
C11 N2 C12 O3 -164.3(2) . . . . ?
C10 N2 C12 O3 -9.2(4) . . . . ?
C11 N2 C12 C13 17.5(3) . . . . ?
C10 N2 C12 C13 172.7(2) . . . . ?
O3 C12 C13 C14 -3.8(4) . . . . ?
N2 C12 C13 C14 174.3(2) . . . . ?
O3 C12 C13 C18 177.7(2) . . . . ?
N2 C12 C13 C18 -4.2(3) . . . . ?
C18 C13 C14 C15 -0.4(4) . . . . ?
C12 C13 C14 C15 -178.9(2) . . . . ?
C13 C14 C15 C16 0.0(4) . . . . ?
C14 C15 C16 C17 0.0(4) . . . . ?
C15 C16 C17 C18 0.2(4) . . . . ?
C11 N3 C18 C13 -10.1(3) . . . . ?
C19 N3 C18 C13 179.8(2) . . . . ?
C11 N3 C18 C17 171.6(2) . . . . ?
C19 N3 C18 C17 1.5(4) . . . . ?
C14 C13 C18 N3 -177.7(2) . . . . ?
C12 C13 C18 N3 0.8(3) . . . . ?
C14 C13 C18 C17 0.6(3) . . . . ?
C12 C13 C18 C17 179.1(2) . . . . ?
C16 C17 C18 N3 177.8(2) . . . . ?
C16 C17 C18 C13 -0.5(4) . . . . ?
C27 N4 C20 C21 174.3(3) . . . . ?
C27 N4 C20 C25 -2.8(3) . . . . ?
C25 C20 C21 C22 -1.0(4) . . . . ?
N4 C20 C21 C22 -177.7(2) . . . . ?
C20 C21 C22 C23 -0.9(4) . . . . ?
C21 C22 C23 C24 1.4(4) . . . . ?
C22 C23 C24 C25 -0.1(4) . . . . ?
C23 C24 C25 C20 -1.7(4) . . . . ?
C23 C24 C25 C26 178.0(2) . . . . ?
C21 C20 C25 C24 2.3(4) . . . . ?
N4 C20 C25 C24 179.6(2) . . . . ?
C21 C20 C25 C26 -177.5(2) . . . . ?
N4 C20 C25 C26 -0.2(3) . . . . ?
C30 O5 C26 C25 177.1(2) . . . . ?
C30 O5 C26 C28 51.7(3) . . . . ?
C30 O5 C26 C27 -71.7(3) . . . . ?
C24 C25 C26 O5 -60.4(3) . . . . ?
C20 C25 C26 O5 119.4(2) . . . . ?
C24 C25 C26 C28 62.7(4) . . . . ?
C20 C25 C26 C28 -117.6(2) . . . . ?
C24 C25 C26 C27 -177.2(3) . . . . ?
C20 C25 C26 C27 2.6(3) . . . . ?
C20 N4 C27 O4 -175.7(3) . . . . ?
C20 N4 C27 C26 4.4(3) . . . . ?
O5 C26 C27 O4 60.5(4) . . . . ?
C25 C26 C27 O4 175.9(3) . . . . ?
C28 C26 C27 O4 -62.1(4) . . . . ?
O5 C26 C27 N4 -119.6(2) . . . . ?
C25 C26 C27 N4 -4.1(3) . . . . ?
C28 C26 C27 N4 117.8(3) . . . . ?
O5 C26 C28 C29 -48.4(3) . . . . ?
C25 C26 C28 C29 -170.7(2) . . . . ?
C27 C26 C28 C29 74.5(3) . . . . ?
C31 N5 C29 C28 100.2(3) . . . . ?
C30 N5 C29 C28 -58.2(3) . . . . ?
C26 C28 C29 N5 51.6(3) . . . . ?
C37 N6 C30 N5 -24.5(4) . . . . ?
C38 N6 C30 N5 172.9(2) . . . . ?
C37 N6 C30 O5 97.7(3) . . . . ?
C38 N6 C30 O5 -64.8(3) . . . . ?
C31 N5 C30 N6 25.5(4) . . . . ?
C29 N5 C30 N6 -177.2(2) . . . . ?
C31 N5 C30 O5 -95.4(3) . . . . ?
C29 N5 C30 O5 61.9(3) . . . . ?
C26 O5 C30 N6 177.0(2) . . . . ?
C26 O5 C30 N5 -59.3(3) . . . . ?
C30 N5 C31 O6 165.5(2) . . . . ?
C29 N5 C31 O6 10.1(4) . . . . ?
C30 N5 C31 C32 -15.9(4) . . . . ?
C29 N5 C31 C32 -171.3(2) . . . . ?
O6 C31 C32 C37 -177.0(3) . . . . ?
N5 C31 C32 C37 4.4(4) . . . . ?
O6 C31 C32 C33 2.8(4) . . . . ?
N5 C31 C32 C33 -175.8(2) . . . . ?
C37 C32 C33 C34 1.5(4) . . . . ?
C31 C32 C33 C34 -178.3(3) . . . . ?
C32 C33 C34 C35 1.3(5) . . . . ?
C33 C34 C35 C36 -2.4(5) . . . . ?
C34 C35 C36 C37 0.7(5) . . . . ?
C30 N6 C37 C32 15.6(4) . . . . ?
C38 N6 C37 C32 176.8(3) . . . . ?
C30 N6 C37 C36 -165.6(2) . . . . ?
C38 N6 C37 C36 -4.4(4) . . . . ?
C33 C32 C37 N6 175.7(3) . . . . ?
C31 C32 C37 N6 -4.5(4) . . . . ?
C33 C32 C37 C36 -3.2(4) . . . . ?
C31 C32 C37 C36 176.6(2) . . . . ?
C35 C36 C37 N6 -176.7(3) . . . . ?
C35 C36 C37 C32 2.1(4) . . . . ?

_refine_diff_density_max         0.172
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.037

_shelxl_version_number           2013-4

