# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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. 
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data_dm15453
_database_code_depnum_ccdc_archive 'CCDC 1513095'
_audit_update_record             
;
2016-10-30 deposited with the CCDC.
2017-05-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H36 N4 O4'
_chemical_formula_weight         612.71

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

_cell_length_a                   27.1608(7)
_cell_length_b                   6.9059(2)
_cell_length_c                   21.9106(9)
_cell_angle_alpha                90
_cell_angle_beta                 127.1100(10)
_cell_angle_gamma                90
_cell_volume                     3277.45(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    3528
_cell_measurement_theta_min      8.164
_cell_measurement_theta_max      137.042

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.653
_shelx_estimated_absorpt_T_min   0.875
_shelx_estimated_absorpt_T_max   0.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5121
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            7732
_diffrn_reflns_av_unetI/netI     0.0729
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         4.164
_diffrn_reflns_theta_max         65.485
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.919
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.919
_diffrn_reflns_point_group_measured_fraction_max 0.700
_diffrn_reflns_point_group_measured_fraction_full 0.663
_reflns_number_total             3942
_reflns_number_gt                3709
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.324
_reflns_Friedel_fraction_max     0.378
_reflns_Friedel_fraction_full    0.357

_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)+(0.0590P)²+1.3240P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 871 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.1(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3942
_refine_ls_number_parameters     433
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1200
_refine_ls_wR_factor_gt          0.1144
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.048
_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
N1 N 0.31636(12) 0.5020(4) 0.32985(15) 0.0281(6) Uani 1 1 d . . . . .
N2 N 0.23007(12) 0.7833(5) 0.16189(14) 0.0354(6) Uani 1 1 d . . . . .
N3 N 0.17747(12) 0.1653(4) 0.16629(15) 0.0303(6) Uani 1 1 d . . . . .
N4 N 0.27173(12) -0.1093(4) 0.33692(14) 0.0330(6) Uani 1 1 d . . . . .
O1 O 0.36260(9) 0.2647(3) 0.31356(10) 0.0273(5) Uani 1 1 d . . . . .
O2 O 0.36429(11) 0.8199(4) -0.01672(12) 0.0376(6) Uani 1 1 d . . . . .
O3 O 0.13186(9) 0.3956(3) 0.18660(10) 0.0274(5) Uani 1 1 d . . . . .
O4 O 0.12930(9) -0.1137(3) 0.50900(11) 0.0287(5) Uani 1 1 d . . . . .
C1 C 0.32541(12) 0.4215(4) 0.28159(15) 0.0240(6) Uani 1 1 d . . . . .
C2 C 0.30072(12) 0.4859(5) 0.20942(15) 0.0245(6) Uani 1 1 d . . . . .
C3 C 0.31162(13) 0.3814(5) 0.15728(15) 0.0275(6) Uani 1 1 d . . . . .
H3 H 0.2750 0.2977 0.1211 0.033 Uiso 1 1 calc R U . . .
C4 C 0.36886(14) 0.2501(5) 0.20804(16) 0.0299(7) Uani 1 1 d . . . . .
H4A H 0.3723 0.1616 0.1753 0.036 Uiso 1 1 calc R U . . .
H4B H 0.4066 0.3309 0.2377 0.036 Uiso 1 1 calc R U . . .
C5 C 0.36369(13) 0.1338(5) 0.26203(16) 0.0291(7) Uani 1 1 d . . . . .
H5 H 0.3237 0.0615 0.2311 0.035 Uiso 1 1 calc R U . . .
C6 C 0.41461(13) -0.0093(5) 0.31150(16) 0.0290(7) Uani 1 1 d . . . . .
C7 C 0.46496(14) -0.0305(5) 0.31020(17) 0.0336(7) Uani 1 1 d . . . . .
H7 H 0.4695 0.0543 0.2797 0.040 Uiso 1 1 calc R U . . .
C8 C 0.50849(15) -0.1738(6) 0.3528(2) 0.0426(9) Uani 1 1 d . . . . .
H8 H 0.5424 -0.1877 0.3510 0.051 Uiso 1 1 calc R U . . .
C9 C 0.50261(17) -0.2957(7) 0.3975(3) 0.0579(11) Uani 1 1 d . . . . .
H9 H 0.5326 -0.3933 0.4274 0.069 Uiso 1 1 calc R U . . .
C10 C 0.45184(17) -0.2745(7) 0.3986(3) 0.0600(12) Uani 1 1 d . . . . .
H10 H 0.4470 -0.3596 0.4287 0.072 Uiso 1 1 calc R U . . .
C11 C 0.40912(15) -0.1316(6) 0.3564(2) 0.0438(9) Uani 1 1 d . . . . .
H11 H 0.3753 -0.1171 0.3584 0.053 Uiso 1 1 calc R U . . .
C12 C 0.26182(13) 0.6476(5) 0.18279(15) 0.0272(7) Uani 1 1 d . . . . .
C13 C 0.32264(12) 0.5131(5) 0.11081(14) 0.0238(6) Uani 1 1 d . . . . .
C14 C 0.35676(13) 0.6812(5) 0.14013(15) 0.0282(6) Uani 1 1 d . . . . .
H14 H 0.3705 0.7247 0.1892 0.034 Uiso 1 1 calc R U . . .
C15 C 0.37165(13) 0.7891(5) 0.09960(15) 0.0279(6) Uani 1 1 d . . . . .
H15 H 0.3952 0.9046 0.1209 0.033 Uiso 1 1 calc R U . . .
C16 C 0.35188(13) 0.7264(5) 0.02808(15) 0.0267(7) Uani 1 1 d . . . . .
C17 C 0.31783(13) 0.5563(5) -0.00210(15) 0.0285(7) Uani 1 1 d . . . . .
H17 H 0.3048 0.5120 -0.0508 0.034 Uiso 1 1 calc R U . . .
C18 C 0.30287(13) 0.4516(5) 0.03817(15) 0.0265(6) Uani 1 1 d . . . . .
H18 H 0.2790 0.3369 0.0166 0.032 Uiso 1 1 calc R U . . .
C19 C 0.39360(18) 1.0042(6) 0.0079(2) 0.0452(9) Uani 1 1 d . . . . .
H19A H 0.3697 1.0905 0.0166 0.068 Uiso 1 1 calc R U . . .
H19B H 0.3958 1.0597 -0.0316 0.068 Uiso 1 1 calc R U . . .
H19C H 0.4354 0.9893 0.0556 0.068 Uiso 1 1 calc R U . . .
C20 C 0.17131(12) 0.2457(4) 0.21708(15) 0.0235(6) Uani 1 1 d . . . . .
C21 C 0.20157(12) 0.1887(4) 0.29156(14) 0.0224(6) Uani 1 1 d . . . . .
C22 C 0.20129(12) 0.3041(4) 0.35031(15) 0.0224(6) Uani 1 1 d . . . . .
H22 H 0.2452 0.3396 0.3919 0.027 Uiso 1 1 calc R U . . .
C23 C 0.16639(12) 0.4946(4) 0.31282(15) 0.0232(6) Uani 1 1 d . . . . .
H23A H 0.1525 0.5494 0.3419 0.028 Uiso 1 1 calc R U . . .
H23B H 0.1944 0.5894 0.3143 0.028 Uiso 1 1 calc R U . . .
C24 C 0.11085(13) 0.4606(4) 0.23041(15) 0.0233(6) Uani 1 1 d . . . . .
H24 H 0.0842 0.3580 0.2291 0.028 Uiso 1 1 calc R U . . .
C25 C 0.07268(12) 0.6398(5) 0.19163(15) 0.0254(6) Uani 1 1 d . . . . .
C26 C 0.02519(13) 0.6839(5) 0.19674(17) 0.0320(7) Uani 1 1 d . . . . .
H26 H 0.0167 0.5984 0.2233 0.038 Uiso 1 1 calc R U . . .
C27 C -0.00977(14) 0.8499(6) 0.16377(19) 0.0383(8) Uani 1 1 d . . . . .
H27 H -0.0414 0.8791 0.1687 0.046 Uiso 1 1 calc R U . . .
C28 C 0.00128(14) 0.9731(6) 0.12383(19) 0.0395(8) Uani 1 1 d . . . . .
H28 H -0.0234 1.0855 0.1000 0.047 Uiso 1 1 calc R U . . .
C29 C 0.04821(15) 0.9331(5) 0.11851(18) 0.0378(8) Uani 1 1 d . . . . .
H29 H 0.0562 1.0194 0.0916 0.045 Uiso 1 1 calc R U . . .
C30 C 0.08420(14) 0.7669(5) 0.15218(17) 0.0322(7) Uani 1 1 d . . . . .
H30 H 0.1165 0.7404 0.1482 0.039 Uiso 1 1 calc R U . . .
C31 C 0.24020(13) 0.0258(5) 0.31629(15) 0.0235(6) Uani 1 1 d . . . . .
C32 C 0.17797(12) 0.1910(4) 0.38775(14) 0.0213(6) Uani 1 1 d . . . . .
C33 C 0.14104(12) 0.0277(4) 0.35552(15) 0.0229(6) Uani 1 1 d . . . . .
H33 H 0.1277 -0.0138 0.3063 0.028 Uiso 1 1 calc R U . . .
C34 C 0.12299(13) -0.0774(5) 0.39337(15) 0.0248(6) Uani 1 1 d . . . . .
H34 H 0.0974 -0.1882 0.3701 0.030 Uiso 1 1 calc R U . . .
C35 C 0.14297(12) -0.0178(5) 0.46555(14) 0.0223(6) Uani 1 1 d . . . . .
C36 C 0.17851(12) 0.1480(5) 0.49799(14) 0.0242(6) Uani 1 1 d . . . . .
H36 H 0.1908 0.1913 0.5465 0.029 Uiso 1 1 calc R U . . .
C37 C 0.19594(12) 0.2498(5) 0.45977(15) 0.0242(6) Uani 1 1 d . . . . .
H37 H 0.2207 0.3625 0.4828 0.029 Uiso 1 1 calc R U . . .
C38 C 0.09776(17) -0.2945(5) 0.48166(19) 0.0404(8) Uani 1 1 d . . . . .
H38A H 0.0564 -0.2740 0.4337 0.061 Uiso 1 1 calc R U . . .
H38B H 0.0942 -0.3509 0.5199 0.061 Uiso 1 1 calc R U . . .
H38C H 0.1210 -0.3828 0.4726 0.061 Uiso 1 1 calc R U . . .
H3B H 0.1973(16) 0.063(7) 0.1758(19) 0.031(9) Uiso 1 1 d . . . . .
H1B H 0.2979(15) 0.625(7) 0.3200(19) 0.032(9) Uiso 1 1 d . . . . .
H3A H 0.1554(14) 0.207(5) 0.1176(18) 0.026(8) Uiso 1 1 d . . . . .
H1A H 0.3312(12) 0.453(5) 0.3724(16) 0.013(7) 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
N1 C1 1.342(4) . ?
N1 H1B 0.95(4) . ?
N1 H1A 0.83(3) . ?
N2 C12 1.164(4) . ?
N3 C20 1.341(4) . ?
N3 H3B 0.83(4) . ?
N3 H3A 0.90(3) . ?
N4 C31 1.158(4) . ?
O1 C1 1.353(4) . ?
O1 C5 1.461(3) . ?
O2 C16 1.376(4) . ?
O2 C19 1.423(4) . ?
O3 C20 1.343(3) . ?
O3 C24 1.452(3) . ?
O4 C35 1.382(3) . ?
O4 C38 1.425(4) . ?
C1 C2 1.367(4) . ?
C2 C12 1.400(4) . ?
C2 C3 1.524(4) . ?
C3 C13 1.523(4) . ?
C3 C4 1.546(4) . ?
C3 H3 1.0000 . ?
C4 C5 1.505(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.501(4) . ?
C5 H5 1.0000 . ?
C6 C11 1.372(5) . ?
C6 C7 1.393(4) . ?
C7 C8 1.384(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.373(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.401(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.371(5) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C13 C14 1.379(4) . ?
C13 C18 1.404(4) . ?
C14 C15 1.393(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.391(4) . ?
C17 C18 1.378(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.369(4) . ?
C21 C31 1.405(4) . ?
C21 C22 1.518(4) . ?
C22 C32 1.520(4) . ?
C22 C23 1.538(4) . ?
C22 H22 1.0000 . ?
C23 C24 1.518(4) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.505(4) . ?
C24 H24 1.0000 . ?
C25 C30 1.393(4) . ?
C25 C26 1.394(4) . ?
C26 C27 1.382(5) . ?
C26 H26 0.9500 . ?
C27 C28 1.377(5) . ?
C27 H27 0.9500 . ?
C28 C29 1.376(5) . ?
C28 H28 0.9500 . ?
C29 C30 1.395(5) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C32 C33 1.386(4) . ?
C32 C37 1.402(4) . ?
C33 C34 1.395(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.389(4) . ?
C34 H34 0.9500 . ?
C35 C36 1.386(4) . ?
C36 C37 1.378(4) . ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 H1B 121(2) . . ?
C1 N1 H1A 121(2) . . ?
H1B N1 H1A 117(3) . . ?
C20 N3 H3B 122(2) . . ?
C20 N3 H3A 122(2) . . ?
H3B N3 H3A 116(3) . . ?
C1 O1 C5 116.9(2) . . ?
C16 O2 C19 118.1(2) . . ?
C20 O3 C24 115.1(2) . . ?
C35 O4 C38 118.3(2) . . ?
N1 C1 O1 111.0(2) . . ?
N1 C1 C2 125.5(3) . . ?
O1 C1 C2 123.5(3) . . ?
C1 C2 C12 117.5(2) . . ?
C1 C2 C3 122.1(3) . . ?
C12 C2 C3 120.3(2) . . ?
C13 C3 C2 115.1(3) . . ?
C13 C3 C4 108.2(2) . . ?
C2 C3 C4 107.7(2) . . ?
C13 C3 H3 108.5 . . ?
C2 C3 H3 108.5 . . ?
C4 C3 H3 108.5 . . ?
C5 C4 C3 110.4(2) . . ?
C5 C4 H4A 109.6 . . ?
C3 C4 H4A 109.6 . . ?
C5 C4 H4B 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
O1 C5 C6 106.8(2) . . ?
O1 C5 C4 109.4(2) . . ?
C6 C5 C4 115.9(2) . . ?
O1 C5 H5 108.2 . . ?
C6 C5 H5 108.2 . . ?
C4 C5 H5 108.2 . . ?
C11 C6 C7 118.9(3) . . ?
C11 C6 C5 118.1(3) . . ?
C7 C6 C5 122.9(3) . . ?
C8 C7 C6 120.8(3) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C9 C8 C7 120.0(3) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 119.2(3) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C11 C10 C9 120.3(4) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C6 120.8(3) . . ?
C10 C11 H11 119.6 . . ?
C6 C11 H11 119.6 . . ?
N2 C12 C2 178.9(3) . . ?
C14 C13 C18 118.2(3) . . ?
C14 C13 C3 122.6(2) . . ?
C18 C13 C3 118.9(3) . . ?
C13 C14 C15 121.7(2) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C16 C15 C14 119.4(3) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
O2 C16 C15 124.5(3) . . ?
O2 C16 C17 115.9(2) . . ?
C15 C16 C17 119.6(3) . . ?
C18 C17 C16 120.5(3) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C13 120.6(3) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N3 C20 O3 111.6(2) . . ?
N3 C20 C21 125.7(3) . . ?
O3 C20 C21 122.6(2) . . ?
C20 C21 C31 117.5(2) . . ?
C20 C21 C22 123.6(3) . . ?
C31 C21 C22 118.6(2) . . ?
C21 C22 C32 113.8(3) . . ?
C21 C22 C23 108.3(2) . . ?
C32 C22 C23 113.9(2) . . ?
C21 C22 H22 106.8 . . ?
C32 C22 H22 106.8 . . ?
C23 C22 H22 106.8 . . ?
C24 C23 C22 110.7(2) . . ?
C24 C23 H23A 109.5 . . ?
C22 C23 H23A 109.5 . . ?
C24 C23 H23B 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 108.1 . . ?
O3 C24 C25 107.0(2) . . ?
O3 C24 C23 109.2(2) . . ?
C25 C24 C23 113.3(2) . . ?
O3 C24 H24 109.1 . . ?
C25 C24 H24 109.1 . . ?
C23 C24 H24 109.1 . . ?
C30 C25 C26 118.5(3) . . ?
C30 C25 C24 122.2(2) . . ?
C26 C25 C24 119.3(3) . . ?
C27 C26 C25 121.1(3) . . ?
C27 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
C28 C27 C26 120.0(3) . . ?
C28 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
C29 C28 C27 119.8(3) . . ?
C29 C28 H28 120.1 . . ?
C27 C28 H28 120.1 . . ?
C28 C29 C30 120.7(3) . . ?
C28 C29 H29 119.7 . . ?
C30 C29 H29 119.7 . . ?
C25 C30 C29 119.9(3) . . ?
C25 C30 H30 120.1 . . ?
C29 C30 H30 120.1 . . ?
N4 C31 C21 179.3(3) . . ?
C33 C32 C37 117.6(3) . . ?
C33 C32 C22 123.5(2) . . ?
C37 C32 C22 118.9(3) . . ?
C32 C33 C34 121.7(2) . . ?
C32 C33 H33 119.1 . . ?
C34 C33 H33 119.1 . . ?
C35 C34 C33 119.1(3) . . ?
C35 C34 H34 120.4 . . ?
C33 C34 H34 120.4 . . ?
O4 C35 C36 115.9(2) . . ?
O4 C35 C34 124.0(3) . . ?
C36 C35 C34 120.1(3) . . ?
C37 C36 C35 119.9(2) . . ?
C37 C36 H36 120.0 . . ?
C35 C36 H36 120.0 . . ?
C36 C37 C32 121.5(3) . . ?
C36 C37 H37 119.3 . . ?
C32 C37 H37 119.3 . . ?
O4 C38 H38A 109.5 . . ?
O4 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
O4 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
C5 O1 C1 N1 164.4(2) . . . . ?
C5 O1 C1 C2 -15.3(4) . . . . ?
N1 C1 C2 C12 -1.1(5) . . . . ?
O1 C1 C2 C12 178.6(3) . . . . ?
N1 C1 C2 C3 -177.8(3) . . . . ?
O1 C1 C2 C3 1.9(4) . . . . ?
C1 C2 C3 C13 -139.7(3) . . . . ?
C12 C2 C3 C13 43.7(4) . . . . ?
C1 C2 C3 C4 -18.9(4) . . . . ?
C12 C2 C3 C4 164.5(3) . . . . ?
C13 C3 C4 C5 173.2(2) . . . . ?
C2 C3 C4 C5 48.2(3) . . . . ?
C1 O1 C5 C6 171.6(2) . . . . ?
C1 O1 C5 C4 45.5(3) . . . . ?
C3 C4 C5 O1 -62.9(3) . . . . ?
C3 C4 C5 C6 176.4(3) . . . . ?
O1 C5 C6 C11 63.9(4) . . . . ?
C4 C5 C6 C11 -174.0(3) . . . . ?
O1 C5 C6 C7 -120.0(3) . . . . ?
C4 C5 C6 C7 2.1(4) . . . . ?
C11 C6 C7 C8 0.7(5) . . . . ?
C5 C6 C7 C8 -175.3(3) . . . . ?
C6 C7 C8 C9 -0.6(5) . . . . ?
C7 C8 C9 C10 0.8(6) . . . . ?
C8 C9 C10 C11 -1.0(7) . . . . ?
C9 C10 C11 C6 1.2(7) . . . . ?
C7 C6 C11 C10 -1.0(5) . . . . ?
C5 C6 C11 C10 175.3(4) . . . . ?
C2 C3 C13 C14 38.5(4) . . . . ?
C4 C3 C13 C14 -82.0(3) . . . . ?
C2 C3 C13 C18 -148.2(3) . . . . ?
C4 C3 C13 C18 91.2(3) . . . . ?
C18 C13 C14 C15 0.0(4) . . . . ?
C3 C13 C14 C15 173.3(3) . . . . ?
C13 C14 C15 C16 -0.1(4) . . . . ?
C19 O2 C16 C15 -7.1(4) . . . . ?
C19 O2 C16 C17 173.9(3) . . . . ?
C14 C15 C16 O2 -179.4(3) . . . . ?
C14 C15 C16 C17 -0.4(4) . . . . ?
O2 C16 C17 C18 -180.0(3) . . . . ?
C15 C16 C17 C18 1.0(4) . . . . ?
C16 C17 C18 C13 -1.1(4) . . . . ?
C14 C13 C18 C17 0.6(4) . . . . ?
C3 C13 C18 C17 -173.0(3) . . . . ?
C24 O3 C20 N3 165.6(3) . . . . ?
C24 O3 C20 C21 -15.6(4) . . . . ?
N3 C20 C21 C31 -3.4(4) . . . . ?
O3 C20 C21 C31 178.0(2) . . . . ?
N3 C20 C21 C22 169.4(3) . . . . ?
O3 C20 C21 C22 -9.2(4) . . . . ?
C20 C21 C22 C32 123.6(3) . . . . ?
C31 C21 C22 C32 -63.7(3) . . . . ?
C20 C21 C22 C23 -4.2(4) . . . . ?
C31 C21 C22 C23 168.6(2) . . . . ?
C21 C22 C23 C24 39.0(3) . . . . ?
C32 C22 C23 C24 -88.7(3) . . . . ?
C20 O3 C24 C25 174.4(2) . . . . ?
C20 O3 C24 C23 51.4(3) . . . . ?
C22 C23 C24 O3 -63.9(3) . . . . ?
C22 C23 C24 C25 176.9(2) . . . . ?
O3 C24 C25 C30 -30.8(3) . . . . ?
C23 C24 C25 C30 89.7(3) . . . . ?
O3 C24 C25 C26 151.0(3) . . . . ?
C23 C24 C25 C26 -88.6(3) . . . . ?
C30 C25 C26 C27 -0.2(4) . . . . ?
C24 C25 C26 C27 178.1(3) . . . . ?
C25 C26 C27 C28 1.3(5) . . . . ?
C26 C27 C28 C29 -1.7(5) . . . . ?
C27 C28 C29 C30 1.0(5) . . . . ?
C26 C25 C30 C29 -0.4(4) . . . . ?
C24 C25 C30 C29 -178.7(3) . . . . ?
C28 C29 C30 C25 0.0(5) . . . . ?
C21 C22 C32 C33 -21.4(4) . . . . ?
C23 C22 C32 C33 103.4(3) . . . . ?
C21 C22 C32 C37 156.7(2) . . . . ?
C23 C22 C32 C37 -78.6(3) . . . . ?
C37 C32 C33 C34 -1.1(4) . . . . ?
C22 C32 C33 C34 176.9(3) . . . . ?
C32 C33 C34 C35 -0.6(4) . . . . ?
C38 O4 C35 C36 -174.3(3) . . . . ?
C38 O4 C35 C34 6.2(4) . . . . ?
C33 C34 C35 O4 -178.2(3) . . . . ?
C33 C34 C35 C36 2.3(4) . . . . ?
O4 C35 C36 C37 178.1(3) . . . . ?
C34 C35 C36 C37 -2.4(4) . . . . ?
C35 C36 C37 C32 0.7(4) . . . . ?
C33 C32 C37 C36 1.0(4) . . . . ?
C22 C32 C37 C36 -177.1(3) . . . . ?

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 H1A O4 0.83(3) 2.18(3) 2.999(3) 168(3) 4_556
N3 H3A O2 0.90(3) 2.09(3) 2.946(3) 160(3) 4_545
N1 H1B N4 0.95(4) 2.08(4) 2.987(4) 161(3) 1_565
N3 H3B N2 0.83(4) 2.22(5) 3.030(4) 162(3) 1_545
C36 H36 N4 0.95 2.51 3.438(4) 164.4 4_556
C17 H17 N2 0.95 2.56 3.466(4) 160.3 4_545

_refine_diff_density_max         0.310
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.067

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_cd15358
_database_code_depnum_ccdc_archive 'CCDC 1512442'
_audit_update_record             
;
2016-10-28 deposited with the CCDC.
2017-05-12 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 H18 N2 O2'
_chemical_formula_weight         306.35

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   9.7979(17)
_cell_length_b                   6.8652(12)
_cell_length_c                   12.478(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.477(4)
_cell_angle_gamma                90
_cell_volume                     836.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1278
_cell_measurement_theta_min      5.097
_cell_measurement_theta_max      41.628

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_F_000             324
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6278
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5058
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.637
_diffrn_reflns_theta_max         25.999
_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 0.937
_diffrn_reflns_point_group_measured_fraction_full 0.942
_reflns_number_total             3081
_reflns_number_gt                2439
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.723
_reflns_Friedel_fraction_max     0.863
_reflns_Friedel_fraction_full    0.873

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_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)+(0.0539P)²] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 872 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -2.7(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3081
_refine_ls_number_parameters     217
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1106
_refine_ls_wR_factor_gt          0.1021
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
N1 N 0.9324(4) 0.7340(5) 0.0077(3) 0.0692(9) Uani 1 1 d . . . . .
N2 N 1.1170(3) 0.4606(6) 0.2034(2) 0.0771(10) Uani 1 1 d . . . . .
O1 O 0.8132(2) 0.9564(3) 0.08760(15) 0.0537(6) Uani 1 1 d . . . . .
O2 O 0.6671(3) 0.4509(5) 0.61784(19) 0.0858(9) Uani 1 1 d . . . . .
C1 C 0.9048(3) 0.8105(5) 0.1024(2) 0.0476(7) Uani 1 1 d . . . . .
C2 C 0.9604(3) 0.7579(5) 0.1995(2) 0.0481(7) Uani 1 1 d . . . . .
C3 C 0.9363(3) 0.8639(5) 0.3024(2) 0.0480(8) Uani 1 1 d . . . . .
H3 H 1.0262 0.8998 0.3366 0.058 Uiso 1 1 calc R U . . .
C4 C 0.8606(3) 1.0531(5) 0.2716(3) 0.0528(8) Uani 1 1 d . . . . .
H4A H 0.8207 1.1062 0.3340 0.063 Uiso 1 1 calc R U . . .
H4B H 0.9247 1.1479 0.2472 0.063 Uiso 1 1 calc R U . . .
C5 C 0.7498(3) 1.0156(4) 0.1839(2) 0.0462(7) Uani 1 1 d . . . . .
H5 H 0.6923 0.9086 0.2064 0.055 Uiso 1 1 calc R U . . .
C6 C 0.6603(3) 1.1874(5) 0.1559(2) 0.0465(7) Uani 1 1 d . . . . .
C7 C 0.5377(3) 1.2021(6) 0.2022(3) 0.0650(10) Uani 1 1 d . . . . .
H7 H 0.5119 1.1046 0.2483 0.078 Uiso 1 1 calc R U . . .
C8 C 0.4538(4) 1.3581(8) 0.1814(4) 0.0861(13) Uani 1 1 d . . . . .
H8 H 0.3710 1.3657 0.2129 0.103 Uiso 1 1 calc R U . . .
C9 C 0.4906(5) 1.5027(7) 0.1148(4) 0.0863(14) Uani 1 1 d . . . . .
H9 H 0.4334 1.6094 0.1011 0.104 Uiso 1 1 calc R U . . .
C10 C 0.6120(4) 1.4906(6) 0.0682(3) 0.0746(11) Uani 1 1 d . . . . .
H10 H 0.6372 1.5887 0.0223 0.090 Uiso 1 1 calc R U . . .
C11 C 0.6968(3) 1.3337(5) 0.0891(3) 0.0581(9) Uani 1 1 d . . . . .
H11 H 0.7798 1.3267 0.0578 0.070 Uiso 1 1 calc R U . . .
C12 C 1.0481(3) 0.5944(6) 0.2032(3) 0.0556(8) Uani 1 1 d . . . . .
C13 C 0.8636(3) 0.7461(4) 0.3833(2) 0.0461(7) Uani 1 1 d . . . . .
C14 C 0.7834(3) 0.5868(5) 0.3558(2) 0.0496(8) Uani 1 1 d . . . . .
H14 H 0.7743 0.5463 0.2845 0.060 Uiso 1 1 calc R U . . .
C15 C 0.7158(3) 0.4851(5) 0.4312(3) 0.0558(8) Uani 1 1 d . . . . .
H15 H 0.6621 0.3779 0.4104 0.067 Uiso 1 1 calc R U . . .
C16 C 0.7280(3) 0.5425(5) 0.5363(3) 0.0572(9) Uani 1 1 d . . . . .
C17 C 0.8066(3) 0.7015(6) 0.5661(3) 0.0621(9) Uani 1 1 d . . . . .
H17 H 0.8145 0.7416 0.6375 0.075 Uiso 1 1 calc R U . . .
C18 C 0.8735(3) 0.8014(5) 0.4910(2) 0.0554(9) Uani 1 1 d . . . . .
H18 H 0.9269 0.9087 0.5124 0.067 Uiso 1 1 calc R U . . .
C19 C 0.5917(6) 0.2803(8) 0.5933(4) 0.1196(19) Uani 1 1 d . . . . .
H19A H 0.5193 0.3082 0.5392 0.179 Uiso 1 1 calc R U . . .
H19B H 0.5534 0.2332 0.6569 0.179 Uiso 1 1 calc R U . . .
H19C H 0.6510 0.1829 0.5671 0.179 Uiso 1 1 calc R U . . .
H1A H 0.885(4) 0.776(7) -0.057(4) 0.101(14) Uiso 1 1 d . . . . .
H1B H 0.998(4) 0.656(7) 0.007(3) 0.077(13) 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
N1 C1 1.340(4) . ?
N1 H1A 0.94(5) . ?
N1 H1B 0.84(5) . ?
N2 C12 1.140(5) . ?
O1 C1 1.348(3) . ?
O1 C5 1.453(3) . ?
O2 C16 1.372(4) . ?
O2 C19 1.405(6) . ?
C1 C2 1.339(4) . ?
C2 C12 1.412(5) . ?
C2 C3 1.510(4) . ?
C3 C13 1.514(4) . ?
C3 C4 1.530(4) . ?
C3 H3 0.9800 . ?
C4 C5 1.502(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.495(4) . ?
C5 H5 0.9800 . ?
C6 C11 1.371(5) . ?
C6 C7 1.377(4) . ?
C7 C8 1.362(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.362(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.367(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.373(5) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C13 C14 1.374(4) . ?
C13 C18 1.393(4) . ?
C14 C15 1.381(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.366(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.370(5) . ?
C17 C18 1.369(5) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
C1 N1 H1A 121(3) . . ?
C1 N1 H1B 118(3) . . ?
H1A N1 H1B 121(4) . . ?
C1 O1 C5 114.7(2) . . ?
C16 O2 C19 118.2(3) . . ?
C2 C1 N1 126.7(3) . . ?
C2 C1 O1 123.0(3) . . ?
N1 C1 O1 110.3(3) . . ?
C1 C2 C12 116.6(3) . . ?
C1 C2 C3 124.0(3) . . ?
C12 C2 C3 119.4(3) . . ?
C2 C3 C13 114.9(3) . . ?
C2 C3 C4 107.5(3) . . ?
C13 C3 C4 112.1(2) . . ?
C2 C3 H3 107.3 . . ?
C13 C3 H3 107.3 . . ?
C4 C3 H3 107.3 . . ?
C5 C4 C3 110.3(2) . . ?
C5 C4 H4A 109.6 . . ?
C3 C4 H4A 109.6 . . ?
C5 C4 H4B 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
O1 C5 C6 108.0(2) . . ?
O1 C5 C4 108.6(2) . . ?
C6 C5 C4 114.4(2) . . ?
O1 C5 H5 108.6 . . ?
C6 C5 H5 108.6 . . ?
C4 C5 H5 108.6 . . ?
C11 C6 C7 118.7(3) . . ?
C11 C6 C5 122.9(3) . . ?
C7 C6 C5 118.4(3) . . ?
C8 C7 C6 120.7(4) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C9 C8 C7 120.3(4) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 119.8(4) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C9 C10 C11 120.0(4) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C6 C11 C10 120.5(3) . . ?
C6 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
N2 C12 C2 178.0(4) . . ?
C14 C13 C18 116.9(3) . . ?
C14 C13 C3 123.3(3) . . ?
C18 C13 C3 119.8(3) . . ?
C13 C14 C15 121.9(3) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 H14 119.1 . . ?
C16 C15 C14 119.8(3) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 119.7(3) . . ?
C15 C16 O2 124.7(3) . . ?
C17 C16 O2 115.6(3) . . ?
C18 C17 C16 120.1(3) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C13 121.5(3) . . ?
C17 C18 H18 119.2 . . ?
C13 C18 H18 119.2 . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O2 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
C5 O1 C1 C2 -16.8(4) . . . . ?
C5 O1 C1 N1 164.9(3) . . . . ?
N1 C1 C2 C12 -5.8(5) . . . . ?
O1 C1 C2 C12 176.1(3) . . . . ?
N1 C1 C2 C3 173.2(3) . . . . ?
O1 C1 C2 C3 -4.9(5) . . . . ?
C1 C2 C3 C13 116.2(3) . . . . ?
C12 C2 C3 C13 -64.8(3) . . . . ?
C1 C2 C3 C4 -9.4(4) . . . . ?
C12 C2 C3 C4 169.6(3) . . . . ?
C2 C3 C4 C5 43.1(3) . . . . ?
C13 C3 C4 C5 -84.2(3) . . . . ?
C1 O1 C5 C6 175.6(2) . . . . ?
C1 O1 C5 C4 51.1(3) . . . . ?
C3 C4 C5 O1 -65.4(3) . . . . ?
C3 C4 C5 C6 174.0(3) . . . . ?
O1 C5 C6 C11 -39.7(4) . . . . ?
C4 C5 C6 C11 81.3(4) . . . . ?
O1 C5 C6 C7 142.6(3) . . . . ?
C4 C5 C6 C7 -96.4(3) . . . . ?
C11 C6 C7 C8 0.6(5) . . . . ?
C5 C6 C7 C8 178.4(3) . . . . ?
C6 C7 C8 C9 -0.5(6) . . . . ?
C7 C8 C9 C10 0.4(6) . . . . ?
C8 C9 C10 C11 -0.5(6) . . . . ?
C7 C6 C11 C10 -0.7(5) . . . . ?
C5 C6 C11 C10 -178.4(3) . . . . ?
C9 C10 C11 C6 0.6(5) . . . . ?
C2 C3 C13 C14 -22.0(4) . . . . ?
C4 C3 C13 C14 101.1(3) . . . . ?
C2 C3 C13 C18 159.8(3) . . . . ?
C4 C3 C13 C18 -77.0(3) . . . . ?
C18 C13 C14 C15 -0.2(4) . . . . ?
C3 C13 C14 C15 -178.4(3) . . . . ?
C13 C14 C15 C16 0.0(5) . . . . ?
C14 C15 C16 C17 0.4(5) . . . . ?
C14 C15 C16 O2 -179.1(3) . . . . ?
C19 O2 C16 C15 3.2(5) . . . . ?
C19 O2 C16 C17 -176.3(4) . . . . ?
C15 C16 C17 C18 -0.6(5) . . . . ?
O2 C16 C17 C18 179.0(3) . . . . ?
C16 C17 C18 C13 0.3(5) . . . . ?
C14 C13 C18 C17 0.1(4) . . . . ?
C3 C13 C18 C17 178.4(3) . . . . ?

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
C17 H17 N2 0.93 2.54 3.415(5) 157.2 2_756
N1 H1B O1 0.84(5) 2.65(5) 3.424(4) 154(4) 2_745
N1 H1A N2 0.94(5) 2.22(5) 3.064(5) 148(4) 2_755

_refine_diff_density_max         0.147
_refine_diff_density_min         -0.112
_refine_diff_density_rms         0.030

_shelxl_version_number           2013-4

