# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1826773'
_audit_update_record             
;
2018-03-01 deposited with the CCDC.
2018-03-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H27 F3 N4 O6'
_chemical_formula_sum            'C25 H27 F3 N4 O6'
_chemical_formula_weight         536.50

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.0578(5)
_cell_length_b                   9.3785(5)
_cell_length_c                   15.7048(9)
_cell_angle_alpha                103.1670(10)
_cell_angle_beta                 101.3370(10)
_cell_angle_gamma                91.8400(10)
_cell_volume                     1269.54(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4666
_cell_measurement_theta_min      3
_cell_measurement_theta_max      30

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.115
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6699
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'APEX2 (Bruker, 2005)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX2 DUO CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15832
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.237
_diffrn_reflns_theta_max         28.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6752
_reflns_number_gt                5494
_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       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'APEX2 (Bruker, 2005)'
_computing_structure_solution    'APEX2 (Bruker, 2005)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/6 (Sheldrick, 2014)'
_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)+(0.0610P)²+0.7136P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6752
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1261
_refine_ls_wR_factor_gt          0.1171
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_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
F1 F -0.03545(13) 0.90642(12) 0.69129(7) 0.0390(3) Uani 1 1 d . . . . .
F2 F -0.00847(11) 1.13627(11) 0.75769(7) 0.0334(2) Uani 1 1 d . . . . .
F3 F -0.12018(11) 0.98167(12) 0.81116(7) 0.0337(2) Uani 1 1 d . . . . .
N1 N 0.43807(13) 0.84064(13) 0.74975(8) 0.0195(2) Uani 1 1 d . . . . .
N2 N 0.49763(13) 0.80307(13) 0.60295(8) 0.0192(2) Uani 1 1 d . . . . .
N3 N 0.30450(12) 0.64189(13) 0.48803(8) 0.0161(2) Uani 1 1 d . . . . .
N4 N 0.14265(13) 0.60153(13) 0.57443(8) 0.0184(2) Uani 1 1 d . . . . .
O1 O 0.11193(15) 1.18152(14) 0.94266(8) 0.0360(3) Uani 1 1 d . . . . .
O2 O 0.31883(13) 1.05772(13) 0.96174(7) 0.0296(3) Uani 1 1 d . . . . .
O3 O 0.34223(15) 0.23688(15) 0.79817(10) 0.0427(3) Uani 1 1 d . . . . .
O4 O 0.50245(14) 0.43928(13) 0.85425(8) 0.0312(3) Uani 1 1 d . . . . .
O5 O 0.06028(11) 0.31919(11) 0.65186(7) 0.0205(2) Uani 1 1 d . . . . .
O6 O 0.27499(11) 0.29049(11) 0.59870(7) 0.0217(2) Uani 1 1 d . . . . .
C1 C 0.22258(15) 0.71273(15) 0.78261(9) 0.0152(2) Uani 1 1 d . . . . .
C2 C 0.14795(16) 0.81753(15) 0.83427(9) 0.0172(3) Uani 1 1 d . . . . .
C3 C 0.06661(17) 0.77494(16) 0.89244(9) 0.0209(3) Uani 1 1 d . . . . .
H3A H 0.0182 0.8463 0.9284 0.025 Uiso 1 1 calc R U . . .
C4 C 0.05553(17) 0.63017(17) 0.89851(10) 0.0227(3) Uani 1 1 d . . . . .
H4A H -0.0022 0.6022 0.9373 0.027 Uiso 1 1 calc R U . . .
C5 C 0.12871(17) 0.52611(16) 0.84787(10) 0.0210(3) Uani 1 1 d . . . . .
H5A H 0.1209 0.4267 0.8520 0.025 Uiso 1 1 calc R U . . .
C6 C 0.21413(15) 0.56691(15) 0.79067(9) 0.0163(3) Uani 1 1 d . . . . .
C7 C 0.30970(15) 0.75176(14) 0.71821(9) 0.0148(2) Uani 1 1 d . . . . .
C8 C 0.52186(16) 0.86198(17) 0.69119(10) 0.0215(3) Uani 1 1 d . . . . .
H8A H 0.6099 0.9275 0.7156 0.026 Uiso 1 1 calc R U . . .
C9 C 0.36775(15) 0.71930(14) 0.57342(9) 0.0150(2) Uani 1 1 d . . . . .
C10 C 0.17010(15) 0.57577(16) 0.49336(9) 0.0181(3) Uani 1 1 d . . . . .
H10A H 0.1026 0.5164 0.4427 0.022 Uiso 1 1 calc R U . . .
C11 C 0.26663(14) 0.69222(14) 0.62659(9) 0.0148(2) Uani 1 1 d . . . . .
C12 C 0.36978(16) 0.63487(17) 0.40800(9) 0.0200(3) Uani 1 1 d . . . . .
H12A H 0.4788 0.6164 0.4237 0.024 Uiso 1 1 calc R U . . .
C13 C 0.3609(2) 0.78120(19) 0.38145(11) 0.0284(3) Uani 1 1 d . . . . .
H13A H 0.4044 0.7754 0.3285 0.043 Uiso 1 1 calc R U . . .
H13B H 0.2551 0.8033 0.3679 0.043 Uiso 1 1 calc R U . . .
H13C H 0.4176 0.8591 0.4309 0.043 Uiso 1 1 calc R U . . .
C14 C 0.29098(19) 0.50781(19) 0.33186(10) 0.0285(3) Uani 1 1 d . . . . .
H14A H 0.3353 0.5045 0.2794 0.043 Uiso 1 1 calc R U . . .
H14B H 0.3039 0.4153 0.3504 0.043 Uiso 1 1 calc R U . . .
H14C H 0.1831 0.5219 0.3168 0.043 Uiso 1 1 calc R U . . .
C15 C 0.14718(16) 0.97574(15) 0.82519(9) 0.0176(3) Uani 1 1 d . . . . .
H15A H 0.2260 0.9916 0.7910 0.021 Uiso 1 1 calc R U . . .
C16 C -0.00394(18) 1.00177(17) 0.77208(10) 0.0237(3) Uani 1 1 d . . . . .
C17 C 0.18714(17) 1.08507(16) 0.91589(10) 0.0211(3) Uani 1 1 d . . . . .
C18 C 0.3682(2) 1.1481(2) 1.05176(12) 0.0399(4) Uani 1 1 d . . . . .
H18A H 0.4657 1.1189 1.0792 0.060 Uiso 1 1 calc R U . . .
H18B H 0.3789 1.2515 1.0497 0.060 Uiso 1 1 calc R U . . .
H18C H 0.2933 1.1351 1.0873 0.060 Uiso 1 1 calc R U . . .
C19 C 0.29763(15) 0.45147(15) 0.73866(9) 0.0168(3) Uani 1 1 d . . . . .
H19A H 0.3741 0.5029 0.7157 0.020 Uiso 1 1 calc R U . . .
C20 C 0.38085(17) 0.36054(17) 0.79934(10) 0.0214(3) Uani 1 1 d . . . . .
C21 C 0.5916(2) 0.3674(2) 0.91857(12) 0.0405(5) Uani 1 1 d . . . . .
H21A H 0.5226 0.3087 0.9415 0.049 Uiso 1 1 calc R U . . .
H21B H 0.6496 0.4433 0.9699 0.049 Uiso 1 1 calc R U . . .
C22 C 0.6975(3) 0.2700(3) 0.87727(14) 0.0590(7) Uani 1 1 d . . . . .
H22A H 0.7551 0.2239 0.9220 0.088 Uiso 1 1 calc R U . . .
H22B H 0.6402 0.1938 0.8271 0.088 Uiso 1 1 calc R U . . .
H22C H 0.7672 0.3282 0.8555 0.088 Uiso 1 1 calc R U . . .
C23 C 0.19302(16) 0.34744(15) 0.65889(9) 0.0173(3) Uani 1 1 d . . . . .
C24 C 0.19689(18) 0.17720(17) 0.52122(10) 0.0254(3) Uani 1 1 d . . . . .
H24A H 0.2509 0.1702 0.4716 0.030 Uiso 1 1 calc R U . . .
H24B H 0.0930 0.2033 0.5008 0.030 Uiso 1 1 calc R U . . .
C25 C 0.1912(2) 0.03188(19) 0.54637(13) 0.0346(4) Uani 1 1 d . . . . .
H25A H 0.1388 -0.0442 0.4944 0.052 Uiso 1 1 calc R U . . .
H25B H 0.2942 0.0060 0.5659 0.052 Uiso 1 1 calc R U . . .
H25C H 0.1368 0.0391 0.5951 0.052 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
F1 C16 1.3473(19) . ?
F2 C16 1.3316(18) . ?
F3 C16 1.3472(18) . ?
N1 C8 1.3455(18) . ?
N1 C7 1.3473(17) . ?
N2 C9 1.3328(18) . ?
N2 C8 1.3407(19) . ?
N3 C9 1.3717(17) . ?
N3 C10 1.3743(17) . ?
N3 C12 1.4800(17) . ?
N4 C10 1.3152(18) . ?
N4 C11 1.3838(17) . ?
O1 C17 1.1991(19) . ?
O2 C17 1.3317(19) . ?
O2 C18 1.449(2) . ?
O3 C20 1.196(2) . ?
O4 C20 1.3365(19) . ?
O4 C21 1.467(2) . ?
O5 C23 1.2008(17) . ?
O6 C23 1.3423(16) . ?
O6 C24 1.4608(18) . ?
C1 C6 1.4030(19) . ?
C1 C2 1.4058(18) . ?
C1 C7 1.4978(18) . ?
C2 C3 1.3961(19) . ?
C2 C15 1.5227(19) . ?
C3 C4 1.384(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.385(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.4011(19) . ?
C5 H5A 0.9500 . ?
C6 C19 1.5178(18) . ?
C7 C11 1.3906(18) . ?
C8 H8A 0.9500 . ?
C9 C11 1.4081(18) . ?
C10 H10A 0.9500 . ?
C12 C13 1.523(2) . ?
C12 C14 1.523(2) . ?
C12 H12A 1.0000 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.515(2) . ?
C15 C17 1.523(2) . ?
C15 H15A 1.0000 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.5274(19) . ?
C19 C23 1.528(2) . ?
C19 H19A 1.0000 . ?
C21 C22 1.486(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C24 C25 1.505(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 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
C8 N1 C7 118.12(12) . . ?
C9 N2 C8 111.73(12) . . ?
C9 N3 C10 105.64(11) . . ?
C9 N3 C12 126.01(11) . . ?
C10 N3 C12 128.34(12) . . ?
C10 N4 C11 103.81(11) . . ?
C17 O2 C18 116.27(13) . . ?
C20 O4 C21 116.48(14) . . ?
C23 O6 C24 116.50(11) . . ?
C6 C1 C2 119.24(12) . . ?
C6 C1 C7 118.85(12) . . ?
C2 C1 C7 121.90(12) . . ?
C3 C2 C1 119.60(13) . . ?
C3 C2 C15 118.79(12) . . ?
C1 C2 C15 121.54(12) . . ?
C4 C3 C2 120.91(13) . . ?
C4 C3 H3A 119.5 . . ?
C2 C3 H3A 119.5 . . ?
C3 C4 C5 119.89(13) . . ?
C3 C4 H4A 120.1 . . ?
C5 C4 H4A 120.1 . . ?
C4 C5 C6 120.24(13) . . ?
C4 C5 H5A 119.9 . . ?
C6 C5 H5A 119.9 . . ?
C5 C6 C1 120.08(12) . . ?
C5 C6 C19 118.96(12) . . ?
C1 C6 C19 120.96(12) . . ?
N1 C7 C11 118.62(12) . . ?
N1 C7 C1 119.44(12) . . ?
C11 C7 C1 121.84(12) . . ?
N2 C8 N1 128.65(13) . . ?
N2 C8 H8A 115.7 . . ?
N1 C8 H8A 115.7 . . ?
N2 C9 N3 128.79(12) . . ?
N2 C9 C11 125.48(12) . . ?
N3 C9 C11 105.73(11) . . ?
N4 C10 N3 114.45(12) . . ?
N4 C10 H10A 122.8 . . ?
N3 C10 H10A 122.8 . . ?
N4 C11 C7 132.39(12) . . ?
N4 C11 C9 110.35(12) . . ?
C7 C11 C9 117.16(12) . . ?
N3 C12 C13 110.13(12) . . ?
N3 C12 C14 110.35(12) . . ?
C13 C12 C14 111.97(13) . . ?
N3 C12 H12A 108.1 . . ?
C13 C12 H12A 108.1 . . ?
C14 C12 H12A 108.1 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C2 110.46(12) . . ?
C16 C15 C17 111.16(12) . . ?
C2 C15 C17 111.84(11) . . ?
C16 C15 H15A 107.7 . . ?
C2 C15 H15A 107.7 . . ?
C17 C15 H15A 107.7 . . ?
F2 C16 F3 106.81(12) . . ?
F2 C16 F1 106.97(12) . . ?
F3 C16 F1 105.96(13) . . ?
F2 C16 C15 113.15(13) . . ?
F3 C16 C15 113.26(12) . . ?
F1 C16 C15 110.24(12) . . ?
O1 C17 O2 124.66(14) . . ?
O1 C17 C15 125.51(14) . . ?
O2 C17 C15 109.82(12) . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C6 C19 C20 110.65(11) . . ?
C6 C19 C23 112.76(11) . . ?
C20 C19 C23 108.66(11) . . ?
C6 C19 H19A 108.2 . . ?
C20 C19 H19A 108.2 . . ?
C23 C19 H19A 108.2 . . ?
O3 C20 O4 124.90(14) . . ?
O3 C20 C19 124.82(14) . . ?
O4 C20 C19 110.28(12) . . ?
O4 C21 C22 111.61(16) . . ?
O4 C21 H21A 109.3 . . ?
C22 C21 H21A 109.3 . . ?
O4 C21 H21B 109.3 . . ?
C22 C21 H21B 109.3 . . ?
H21A C21 H21B 108.0 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O5 C23 O6 125.63(13) . . ?
O5 C23 C19 125.80(13) . . ?
O6 C23 C19 108.56(11) . . ?
O6 C24 C25 109.44(13) . . ?
O6 C24 H24A 109.8 . . ?
C25 C24 H24A 109.8 . . ?
O6 C24 H24B 109.8 . . ?
C25 C24 H24B 109.8 . . ?
H24A C24 H24B 108.2 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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 -0.1(2) . . . . ?
C7 C1 C2 C3 179.15(13) . . . . ?
C6 C1 C2 C15 -177.17(12) . . . . ?
C7 C1 C2 C15 2.1(2) . . . . ?
C1 C2 C3 C4 -1.5(2) . . . . ?
C15 C2 C3 C4 175.63(14) . . . . ?
C2 C3 C4 C5 1.5(2) . . . . ?
C3 C4 C5 C6 0.1(2) . . . . ?
C4 C5 C6 C1 -1.7(2) . . . . ?
C4 C5 C6 C19 177.78(13) . . . . ?
C2 C1 C6 C5 1.7(2) . . . . ?
C7 C1 C6 C5 -177.59(13) . . . . ?
C2 C1 C6 C19 -177.78(12) . . . . ?
C7 C1 C6 C19 2.91(19) . . . . ?
C8 N1 C7 C11 -2.97(19) . . . . ?
C8 N1 C7 C1 173.44(13) . . . . ?
C6 C1 C7 N1 -112.68(15) . . . . ?
C2 C1 C7 N1 68.03(17) . . . . ?
C6 C1 C7 C11 63.61(17) . . . . ?
C2 C1 C7 C11 -115.68(15) . . . . ?
C9 N2 C8 N1 3.5(2) . . . . ?
C7 N1 C8 N2 -1.8(2) . . . . ?
C8 N2 C9 N3 179.76(13) . . . . ?
C8 N2 C9 C11 -0.7(2) . . . . ?
C10 N3 C9 N2 -179.26(14) . . . . ?
C12 N3 C9 N2 0.1(2) . . . . ?
C10 N3 C9 C11 1.12(14) . . . . ?
C12 N3 C9 C11 -179.53(12) . . . . ?
C11 N4 C10 N3 0.60(16) . . . . ?
C9 N3 C10 N4 -1.13(16) . . . . ?
C12 N3 C10 N4 179.54(13) . . . . ?
C10 N4 C11 C7 -176.15(14) . . . . ?
C10 N4 C11 C9 0.17(15) . . . . ?
N1 C7 C11 N4 -178.60(14) . . . . ?
C1 C7 C11 N4 5.1(2) . . . . ?
N1 C7 C11 C9 5.27(18) . . . . ?
C1 C7 C11 C9 -171.05(12) . . . . ?
N2 C9 C11 N4 179.54(13) . . . . ?
N3 C9 C11 N4 -0.83(15) . . . . ?
N2 C9 C11 C7 -3.5(2) . . . . ?
N3 C9 C11 C7 176.11(11) . . . . ?
C9 N3 C12 C13 -71.32(17) . . . . ?
C10 N3 C12 C13 107.88(16) . . . . ?
C9 N3 C12 C14 164.56(13) . . . . ?
C10 N3 C12 C14 -16.2(2) . . . . ?
C3 C2 C15 C16 -73.56(16) . . . . ?
C1 C2 C15 C16 103.50(15) . . . . ?
C3 C2 C15 C17 50.82(17) . . . . ?
C1 C2 C15 C17 -132.13(14) . . . . ?
C2 C15 C16 F2 -176.49(12) . . . . ?
C17 C15 C16 F2 58.75(16) . . . . ?
C2 C15 C16 F3 61.77(16) . . . . ?
C17 C15 C16 F3 -63.00(16) . . . . ?
C2 C15 C16 F1 -56.75(16) . . . . ?
C17 C15 C16 F1 178.48(12) . . . . ?
C18 O2 C17 O1 3.1(2) . . . . ?
C18 O2 C17 C15 -176.74(14) . . . . ?
C16 C15 C17 O1 -1.1(2) . . . . ?
C2 C15 C17 O1 -125.12(16) . . . . ?
C16 C15 C17 O2 178.75(12) . . . . ?
C2 C15 C17 O2 54.76(16) . . . . ?
C5 C6 C19 C20 -45.77(17) . . . . ?
C1 C6 C19 C20 133.73(13) . . . . ?
C5 C6 C19 C23 76.15(16) . . . . ?
C1 C6 C19 C23 -104.34(14) . . . . ?
C21 O4 C20 O3 -1.4(2) . . . . ?
C21 O4 C20 C19 178.26(13) . . . . ?
C6 C19 C20 O3 105.94(18) . . . . ?
C23 C19 C20 O3 -18.4(2) . . . . ?
C6 C19 C20 O4 -73.70(15) . . . . ?
C23 C19 C20 O4 162.00(12) . . . . ?
C20 O4 C21 C22 82.1(2) . . . . ?
C24 O6 C23 O5 -4.4(2) . . . . ?
C24 O6 C23 C19 174.34(11) . . . . ?
C6 C19 C23 O5 -25.24(19) . . . . ?
C20 C19 C23 O5 97.80(16) . . . . ?
C6 C19 C23 O6 156.01(11) . . . . ?
C20 C19 C23 O6 -80.95(13) . . . . ?
C23 O6 C24 C25 -81.06(16) . . . . ?

_refine_diff_density_max         0.422
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.053

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1826774'
_audit_update_record             
;
2018-03-01 deposited with the CCDC.
2018-03-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H24 N4 O4'
_chemical_formula_sum            'C21 H24 N4 O4'
_chemical_formula_weight         396.44

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                   9.7486(10)
_cell_length_b                   10.5135(11)
_cell_length_c                   19.312(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.750(2)
_cell_angle_gamma                90
_cell_volume                     1944.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3522
_cell_measurement_theta_min      3
_cell_measurement_theta_max      30

_exptl_crystal_description       prism
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6699
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'APEX2 (Bruker, 2005)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX2 CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25772
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.147
_diffrn_reflns_theta_max         30.717
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6036
_reflns_number_gt                4931
_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       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'APEX2 (Bruker, 2005)'
_computing_structure_solution    'APEX2 (Bruker, 2005)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/6 (Sheldrick, 2014)'
_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)+(0.0600P)²+0.5000P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6036
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1180
_refine_ls_wR_factor_gt          0.1092
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_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 0.28166(10) 0.42076(9) 0.30040(5) 0.0230(2) Uani 1 1 d . . . . .
O2 O 0.45502(9) 0.51177(8) 0.37846(4) 0.01747(17) Uani 1 1 d . . . . .
O3 O 0.54236(9) 0.21850(8) 0.33119(4) 0.02058(19) Uani 1 1 d . . . . .
O4 O 0.57515(9) 0.16744(8) 0.44659(4) 0.01779(18) Uani 1 1 d . . . . .
N1 N 0.21332(10) 0.46883(9) 0.46653(5) 0.01478(19) Uani 1 1 d . . . . .
N2 N 0.19412(10) 0.58644(9) 0.57162(5) 0.01628(19) Uani 1 1 d . . . . .
N3 N 0.11320(10) 0.45370(9) 0.65950(5) 0.01506(19) Uani 1 1 d . . . . .
N4 N 0.08731(11) 0.26749(9) 0.59961(5) 0.0183(2) Uani 1 1 d . . . . .
C1 C 0.16526(11) 0.24360(10) 0.44781(5) 0.0121(2) Uani 1 1 d . . . . .
C2 C 0.05844(11) 0.15553(10) 0.44974(6) 0.0140(2) Uani 1 1 d . . . . .
H2A H -0.0061 0.1700 0.4802 0.017 Uiso 1 1 calc R U . . .
C3 C 0.04532(12) 0.04741(11) 0.40789(6) 0.0158(2) Uani 1 1 d . . . . .
H3A H -0.0266 -0.0125 0.4103 0.019 Uiso 1 1 calc R U . . .
C4 C 0.13788(12) 0.02737(11) 0.36247(6) 0.0164(2) Uani 1 1 d . . . . .
H4A H 0.1278 -0.0452 0.3326 0.020 Uiso 1 1 calc R U . . .
C5 C 0.24552(12) 0.11342(11) 0.36054(6) 0.0153(2) Uani 1 1 d . . . . .
H5A H 0.3083 0.0987 0.3292 0.018 Uiso 1 1 calc R U . . .
C6 C 0.26295(11) 0.22090(10) 0.40371(5) 0.0121(2) Uani 1 1 d . . . . .
C7 C 0.17039(11) 0.35944(10) 0.49206(5) 0.0121(2) Uani 1 1 d . . . . .
C8 C 0.22183(13) 0.57386(11) 0.50680(6) 0.0170(2) Uani 1 1 d . . . . .
H8A H 0.2514 0.6490 0.4865 0.020 Uiso 1 1 calc R U . . .
C9 C 0.15026(11) 0.47740(10) 0.59538(6) 0.0134(2) Uani 1 1 d . . . . .
C10 C 0.07784(13) 0.32776(11) 0.65823(6) 0.0182(2) Uani 1 1 d . . . . .
H10A H 0.0486 0.2868 0.6968 0.022 Uiso 1 1 calc R U . . .
C11 C 0.13381(11) 0.36115(10) 0.55869(6) 0.0134(2) Uani 1 1 d . . . . .
C12 C 0.13499(12) 0.53299(11) 0.72358(6) 0.0159(2) Uani 1 1 d . . . . .
H12A H 0.0851 0.4913 0.7583 0.019 Uiso 1 1 calc R U . . .
C13 C 0.07414(15) 0.66476(13) 0.70890(7) 0.0256(3) Uani 1 1 d . . . . .
H13A H 0.0865 0.7132 0.7530 0.038 Uiso 1 1 calc R U . . .
H13B H -0.0256 0.6580 0.6888 0.038 Uiso 1 1 calc R U . . .
H13C H 0.1221 0.7084 0.6754 0.038 Uiso 1 1 calc R U . . .
C14 C 0.28967(13) 0.53576(13) 0.75566(7) 0.0229(3) Uani 1 1 d . . . . .
H14A H 0.3040 0.5849 0.7996 0.034 Uiso 1 1 calc R U . . .
H14B H 0.3413 0.5755 0.7225 0.034 Uiso 1 1 calc R U . . .
H14C H 0.3234 0.4487 0.7657 0.034 Uiso 1 1 calc R U . . .
C15 C 0.39008(11) 0.30636(10) 0.40556(5) 0.0126(2) Uani 1 1 d . . . . .
H15A H 0.4181 0.3407 0.4544 0.015 Uiso 1 1 calc R U . . .
C16 C 0.36490(12) 0.41823(11) 0.35475(6) 0.0150(2) Uani 1 1 d . . . . .
C17 C 0.44818(13) 0.62438(11) 0.33426(7) 0.0205(2) Uani 1 1 d . . . . .
H17A H 0.4314 0.5983 0.2841 0.025 Uiso 1 1 calc R U . . .
H17B H 0.5388 0.6695 0.3446 0.025 Uiso 1 1 calc R U . . .
C18 C 0.33394(16) 0.71331(13) 0.34618(8) 0.0303(3) Uani 1 1 d . . . . .
H18A H 0.3282 0.7850 0.3133 0.045 Uiso 1 1 calc R U . . .
H18B H 0.3545 0.7452 0.3947 0.045 Uiso 1 1 calc R U . . .
H18C H 0.2447 0.6677 0.3383 0.045 Uiso 1 1 calc R U . . .
C19 C 0.51135(11) 0.22788(10) 0.38855(6) 0.0141(2) Uani 1 1 d . . . . .
C20 C 0.68286(13) 0.07563(12) 0.43750(7) 0.0229(3) Uani 1 1 d . . . . .
H20A H 0.7519 0.0682 0.4819 0.028 Uiso 1 1 calc R U . . .
H20B H 0.7323 0.1055 0.4002 0.028 Uiso 1 1 calc R U . . .
C21 C 0.61803(15) -0.05246(12) 0.41756(7) 0.0245(3) Uani 1 1 d . . . . .
H21A H 0.6913 -0.1136 0.4123 0.037 Uiso 1 1 calc R U . . .
H21B H 0.5516 -0.0453 0.3729 0.037 Uiso 1 1 calc R U . . .
H21C H 0.5690 -0.0818 0.4545 0.037 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 C16 1.2013(14) . ?
O2 C16 1.3412(14) . ?
O2 C17 1.4537(14) . ?
O3 C19 1.2055(14) . ?
O4 C19 1.3368(14) . ?
O4 C20 1.4608(14) . ?
N1 C8 1.3443(14) . ?
N1 C7 1.3484(14) . ?
N2 C9 1.3345(14) . ?
N2 C8 1.3355(15) . ?
N3 C10 1.3673(15) . ?
N3 C9 1.3758(14) . ?
N3 C12 1.4742(14) . ?
N4 C10 1.3156(15) . ?
N4 C11 1.3903(14) . ?
C1 C2 1.3992(15) . ?
C1 C6 1.4112(15) . ?
C1 C7 1.4833(14) . ?
C2 C3 1.3867(15) . ?
C2 H2A 0.9500 . ?
C3 C4 1.3868(16) . ?
C3 H3A 0.9500 . ?
C4 C5 1.3913(16) . ?
C4 H4A 0.9500 . ?
C5 C6 1.3958(15) . ?
C5 H5A 0.9500 . ?
C6 C15 1.5257(15) . ?
C7 C11 1.3980(15) . ?
C8 H8A 0.9500 . ?
C9 C11 1.4068(15) . ?
C10 H10A 0.9500 . ?
C12 C13 1.5129(17) . ?
C12 C14 1.5199(17) . ?
C12 H12A 1.0000 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.5221(15) . ?
C15 C19 1.5269(15) . ?
C15 H15A 1.0000 . ?
C17 C18 1.5043(19) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C20 C21 1.5068(19) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
C16 O2 C17 116.18(9) . . ?
C19 O4 C20 116.47(9) . . ?
C8 N1 C7 118.61(10) . . ?
C9 N2 C8 111.78(9) . . ?
C10 N3 C9 105.48(9) . . ?
C10 N3 C12 123.99(9) . . ?
C9 N3 C12 129.21(10) . . ?
C10 N4 C11 103.33(10) . . ?
C2 C1 C6 119.57(10) . . ?
C2 C1 C7 118.25(9) . . ?
C6 C1 C7 122.17(10) . . ?
C3 C2 C1 121.00(10) . . ?
C3 C2 H2A 119.5 . . ?
C1 C2 H2A 119.5 . . ?
C2 C3 C4 119.54(10) . . ?
C2 C3 H3A 120.2 . . ?
C4 C3 H3A 120.2 . . ?
C3 C4 C5 120.08(10) . . ?
C3 C4 H4A 120.0 . . ?
C5 C4 H4A 120.0 . . ?
C4 C5 C6 121.25(10) . . ?
C4 C5 H5A 119.4 . . ?
C6 C5 H5A 119.4 . . ?
C5 C6 C1 118.47(10) . . ?
C5 C6 C15 119.90(9) . . ?
C1 C6 C15 121.53(9) . . ?
N1 C7 C11 118.39(10) . . ?
N1 C7 C1 117.97(9) . . ?
C11 C7 C1 123.63(10) . . ?
N2 C8 N1 128.48(10) . . ?
N2 C8 H8A 115.8 . . ?
N1 C8 H8A 115.8 . . ?
N2 C9 N3 128.31(10) . . ?
N2 C9 C11 125.93(10) . . ?
N3 C9 C11 105.76(9) . . ?
N4 C10 N3 115.08(10) . . ?
N4 C10 H10A 122.5 . . ?
N3 C10 H10A 122.5 . . ?
N4 C11 C7 132.86(10) . . ?
N4 C11 C9 110.35(9) . . ?
C7 C11 C9 116.75(10) . . ?
N3 C12 C13 111.75(9) . . ?
N3 C12 C14 109.25(9) . . ?
C13 C12 C14 112.54(11) . . ?
N3 C12 H12A 107.7 . . ?
C13 C12 H12A 107.7 . . ?
C14 C12 H12A 107.7 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C6 114.04(9) . . ?
C16 C15 C19 108.49(9) . . ?
C6 C15 C19 109.57(9) . . ?
C16 C15 H15A 108.2 . . ?
C6 C15 H15A 108.2 . . ?
C19 C15 H15A 108.2 . . ?
O1 C16 O2 125.09(11) . . ?
O1 C16 C15 125.58(10) . . ?
O2 C16 C15 109.26(9) . . ?
O2 C17 C18 111.75(10) . . ?
O2 C17 H17A 109.3 . . ?
C18 C17 H17A 109.3 . . ?
O2 C17 H17B 109.3 . . ?
C18 C17 H17B 109.3 . . ?
H17A C17 H17B 107.9 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 C19 O4 125.06(11) . . ?
O3 C19 C15 125.37(10) . . ?
O4 C19 C15 109.53(9) . . ?
O4 C20 C21 110.16(10) . . ?
O4 C20 H20A 109.6 . . ?
C21 C20 H20A 109.6 . . ?
O4 C20 H20B 109.6 . . ?
C21 C20 H20B 109.6 . . ?
H20A C20 H20B 108.1 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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 -1.31(16) . . . . ?
C7 C1 C2 C3 177.91(10) . . . . ?
C1 C2 C3 C4 -1.20(17) . . . . ?
C2 C3 C4 C5 1.88(17) . . . . ?
C3 C4 C5 C6 -0.02(17) . . . . ?
C4 C5 C6 C1 -2.46(16) . . . . ?
C4 C5 C6 C15 174.04(10) . . . . ?
C2 C1 C6 C5 3.10(15) . . . . ?
C7 C1 C6 C5 -176.09(10) . . . . ?
C2 C1 C6 C15 -173.34(10) . . . . ?
C7 C1 C6 C15 7.47(15) . . . . ?
C8 N1 C7 C11 1.38(16) . . . . ?
C8 N1 C7 C1 -178.35(10) . . . . ?
C2 C1 C7 N1 -144.77(10) . . . . ?
C6 C1 C7 N1 34.43(15) . . . . ?
C2 C1 C7 C11 35.51(15) . . . . ?
C6 C1 C7 C11 -145.30(11) . . . . ?
C9 N2 C8 N1 -1.45(18) . . . . ?
C7 N1 C8 N2 0.73(19) . . . . ?
C8 N2 C9 N3 179.50(11) . . . . ?
C8 N2 C9 C11 0.09(16) . . . . ?
C10 N3 C9 N2 -179.29(12) . . . . ?
C12 N3 C9 N2 -12.22(19) . . . . ?
C10 N3 C9 C11 0.21(12) . . . . ?
C12 N3 C9 C11 167.28(11) . . . . ?
C11 N4 C10 N3 0.43(14) . . . . ?
C9 N3 C10 N4 -0.42(14) . . . . ?
C12 N3 C10 N4 -168.35(11) . . . . ?
C10 N4 C11 C7 176.99(12) . . . . ?
C10 N4 C11 C9 -0.27(13) . . . . ?
N1 C7 C11 N4 -179.59(11) . . . . ?
C1 C7 C11 N4 0.13(19) . . . . ?
N1 C7 C11 C9 -2.48(15) . . . . ?
C1 C7 C11 C9 177.25(10) . . . . ?
N2 C9 C11 N4 179.55(11) . . . . ?
N3 C9 C11 N4 0.03(13) . . . . ?
N2 C9 C11 C7 1.80(17) . . . . ?
N3 C9 C11 C7 -177.72(9) . . . . ?
C10 N3 C12 C13 -139.72(12) . . . . ?
C9 N3 C12 C13 55.36(16) . . . . ?
C10 N3 C12 C14 95.07(13) . . . . ?
C9 N3 C12 C14 -69.85(15) . . . . ?
C5 C6 C15 C16 93.64(12) . . . . ?
C1 C6 C15 C16 -89.96(12) . . . . ?
C5 C6 C15 C19 -28.16(13) . . . . ?
C1 C6 C15 C19 148.23(10) . . . . ?
C17 O2 C16 O1 0.67(17) . . . . ?
C17 O2 C16 C15 177.76(9) . . . . ?
C6 C15 C16 O1 -27.68(16) . . . . ?
C19 C15 C16 O1 94.72(13) . . . . ?
C6 C15 C16 O2 155.24(9) . . . . ?
C19 C15 C16 O2 -82.36(11) . . . . ?
C16 O2 C17 C18 82.28(13) . . . . ?
C20 O4 C19 O3 -5.23(16) . . . . ?
C20 O4 C19 C15 172.64(9) . . . . ?
C16 C15 C19 O3 -29.23(15) . . . . ?
C6 C15 C19 O3 95.85(13) . . . . ?
C16 C15 C19 O4 152.91(9) . . . . ?
C6 C15 C19 O4 -82.01(11) . . . . ?
C19 O4 C20 C21 -86.56(13) . . . . ?

_refine_diff_density_max         0.388
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.066

_shelxl_version_number           2014/6

