# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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. 
# 
#######################################################################

data_cd214308
_database_code_depnum_ccdc_archive 'CCDC 1005236'
_audit_update_record             
;
2014-05-26 deposited with the CCDC.
2017-09-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H20 Cl F3 N2 O3'
_chemical_formula_weight         464.86

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   18.1727(15)
_cell_length_b                   10.5743(9)
_cell_length_c                   23.8130(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4576.0(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2385
_cell_measurement_theta_min      4.774
_cell_measurement_theta_max      39.755

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_F_000             1920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.112
_exptl_absorpt_coefficient_mu    0.218
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6652
_exptl_absorpt_correction_T_max  0.7457
_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            26342
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.710
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4486
_reflns_number_gt                2660
_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 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)+(0.0530P)²+1.5614P] 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_number_reflns         4486
_refine_ls_number_parameters     295
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1089
_refine_ls_R_factor_gt           0.0596
_refine_ls_wR_factor_ref         0.1478
_refine_ls_wR_factor_gt          0.1255
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.031
_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
Cl1 Cl 0.16853(5) 0.06333(9) 0.13257(4) 0.0854(3) Uani 1 1 d . . . . .
F1 F 0.51345(9) 0.16623(17) 0.01912(9) 0.0876(6) Uani 1 1 d . . . . .
F2 F 0.42462(11) 0.04742(17) 0.04596(9) 0.0907(6) Uani 1 1 d . . . . .
F3 F 0.41550(11) 0.1535(2) -0.03026(9) 0.0990(7) Uani 1 1 d . . . . .
N1 N 0.43069(13) 0.3841(2) 0.02617(10) 0.0540(6) Uani 1 1 d D . . . .
N2 N 0.31837(11) 0.4295(2) -0.01585(9) 0.0525(6) Uani 1 1 d . . . . .
O1 O 0.42163(10) 0.5393(2) -0.03756(9) 0.0699(6) Uani 1 1 d . . . . .
O2 O 0.5833(2) 0.5329(4) 0.30251(14) 0.1617(16) Uani 1 1 d . . . . .
O3 O 0.18774(16) 0.2201(3) -0.24717(11) 0.1136(9) Uani 1 1 d . . . . .
C1 C 0.32393(13) 0.2618(2) 0.05389(11) 0.0470(6) Uani 1 1 d . . . . .
C2 C 0.28801(15) 0.1767(3) 0.08851(11) 0.0558(7) Uani 1 1 d . . . . .
H2 H 0.3151 0.1246 0.1122 0.067 Uiso 1 1 calc R U . . .
C3 C 0.21215(16) 0.1688(3) 0.08806(12) 0.0602(8) Uani 1 1 d . . . . .
C4 C 0.17170(16) 0.2433(3) 0.05259(13) 0.0639(8) Uani 1 1 d . . . . .
H4 H 0.1207 0.2363 0.0519 0.077 Uiso 1 1 calc R U . . .
C5 C 0.20631(15) 0.3281(3) 0.01819(12) 0.0603(8) Uani 1 1 d . . . . .
H5 H 0.1785 0.3785 -0.0057 0.072 Uiso 1 1 calc R U . . .
C6 C 0.28330(14) 0.3399(2) 0.01850(11) 0.0490(7) Uani 1 1 d . . . . .
C7 C 0.39208(15) 0.4546(3) -0.01038(11) 0.0514(7) Uani 1 1 d . . . . .
C8 C 0.40750(13) 0.2709(3) 0.05458(11) 0.0484(6) Uani 1 1 d . . . . .
C9 C 0.44011(16) 0.1584(3) 0.02233(14) 0.0664(8) Uani 1 1 d . . . . .
C10 C 0.43654(14) 0.2662(3) 0.11393(11) 0.0532(7) Uani 1 1 d . . . . .
H10 H 0.4295 0.1913 0.1337 0.064 Uiso 1 1 calc R U . . .
C11 C 0.47073(16) 0.3578(3) 0.14019(12) 0.0597(8) Uani 1 1 d . . . . .
H11 H 0.4821 0.4307 0.1201 0.072 Uiso 1 1 calc R U . . .
C12 C 0.49172(17) 0.3517(3) 0.19851(13) 0.0698(9) Uani 1 1 d . . . . .
H12 H 0.4800 0.2788 0.2184 0.084 Uiso 1 1 calc R U . . .
C13 C 0.5268(2) 0.4439(4) 0.22568(16) 0.0971(12) Uani 1 1 d . . . . .
H13 H 0.5389 0.5156 0.2050 0.117 Uiso 1 1 calc R U . . .
C14 C 0.5480(3) 0.4428(5) 0.28443(19) 0.1148(16) Uani 1 1 d . . . . .
C15 C 0.5274(3) 0.3328(5) 0.32118(18) 0.144(2) Uani 1 1 d . . . . .
H15A H 0.5531 0.2585 0.3089 0.216 Uiso 1 1 calc R U . . .
H15B H 0.4753 0.3186 0.3188 0.216 Uiso 1 1 calc R U . . .
H15C H 0.5405 0.3511 0.3594 0.216 Uiso 1 1 calc R U . . .
C16 C 0.27638(15) 0.5030(3) -0.05709(12) 0.0604(8) Uani 1 1 d . . . . .
H16A H 0.3062 0.5733 -0.0699 0.072 Uiso 1 1 calc R U . . .
H16B H 0.2330 0.5375 -0.0390 0.072 Uiso 1 1 calc R U . . .
C17 C 0.25300(16) 0.4256(3) -0.10711(12) 0.0601(8) Uani 1 1 d . . . . .
C18 C 0.3015(2) 0.3483(4) -0.13462(16) 0.0984(13) Uani 1 1 d . . . . .
H18 H 0.3495 0.3429 -0.1214 0.118 Uiso 1 1 calc R U . . .
C19 C 0.2821(2) 0.2786(4) -0.18092(16) 0.1051(14) Uani 1 1 d . . . . .
H19 H 0.3167 0.2271 -0.1984 0.126 Uiso 1 1 calc R U . . .
C20 C 0.2127(2) 0.2848(4) -0.20117(14) 0.0794(10) Uani 1 1 d . . . . .
C21 C 0.1628(2) 0.3604(4) -0.17431(17) 0.0993(13) Uani 1 1 d . . . . .
H21 H 0.1148 0.3650 -0.1877 0.119 Uiso 1 1 calc R U . . .
C22 C 0.18244(18) 0.4297(4) -0.12806(15) 0.0863(11) Uani 1 1 d . . . . .
H22 H 0.1475 0.4803 -0.1105 0.104 Uiso 1 1 calc R U . . .
C23 C 0.2387(3) 0.1422(5) -0.27615(18) 0.1328(18) Uani 1 1 d . . . . .
H23A H 0.2809 0.1914 -0.2867 0.199 Uiso 1 1 calc R U . . .
H23B H 0.2158 0.1083 -0.3092 0.199 Uiso 1 1 calc R U . . .
H23C H 0.2538 0.0741 -0.2521 0.199 Uiso 1 1 calc R U . . .
H1 H 0.4751(10) 0.402(2) 0.0291(10) 0.053(8) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C3 1.730(3) . ?
F1 C9 1.338(3) . ?
F2 C9 1.332(4) . ?
F3 C9 1.331(4) . ?
N1 C7 1.344(3) . ?
N1 C8 1.439(3) . ?
N1 H1 0.832(17) . ?
N2 C7 1.372(3) . ?
N2 C6 1.405(3) . ?
N2 C16 1.466(3) . ?
O1 C7 1.228(3) . ?
O2 C14 1.226(5) . ?
O3 C20 1.368(4) . ?
O3 C23 1.419(5) . ?
C1 C2 1.384(4) . ?
C1 C6 1.392(4) . ?
C1 C8 1.522(3) . ?
C2 C3 1.381(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.370(4) . ?
C4 C5 1.367(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.405(4) . ?
C5 H5 0.9300 . ?
C8 C10 1.509(4) . ?
C8 C9 1.535(4) . ?
C10 C11 1.309(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.441(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.333(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.451(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.503(6) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.506(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.368(4) . ?
C17 C22 1.377(4) . ?
C18 C19 1.372(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.353(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.368(5) . ?
C21 C22 1.370(5) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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 N1 C8 127.9(2) . . ?
C7 N1 H1 115.9(19) . . ?
C8 N1 H1 115.5(19) . . ?
C7 N2 C6 121.2(2) . . ?
C7 N2 C16 118.0(2) . . ?
C6 N2 C16 120.7(2) . . ?
C20 O3 C23 117.6(3) . . ?
C2 C1 C6 119.7(2) . . ?
C2 C1 C8 120.4(2) . . ?
C6 C1 C8 119.9(2) . . ?
C3 C2 C1 120.4(3) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 Cl1 120.2(2) . . ?
C2 C3 Cl1 119.4(2) . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 N2 120.8(2) . . ?
C1 C6 C5 118.6(3) . . ?
N2 C6 C5 120.6(2) . . ?
O1 C7 N1 121.2(2) . . ?
O1 C7 N2 121.2(2) . . ?
N1 C7 N2 117.6(2) . . ?
N1 C8 C10 111.4(2) . . ?
N1 C8 C1 109.9(2) . . ?
C10 C8 C1 110.9(2) . . ?
N1 C8 C9 107.3(2) . . ?
C10 C8 C9 108.0(2) . . ?
C1 C8 C9 109.3(2) . . ?
F3 C9 F2 107.0(3) . . ?
F3 C9 F1 106.5(3) . . ?
F2 C9 F1 106.8(3) . . ?
F3 C9 C8 111.8(3) . . ?
F2 C9 C8 112.9(3) . . ?
F1 C9 C8 111.4(2) . . ?
C11 C10 C8 126.1(3) . . ?
C11 C10 H10 116.9 . . ?
C8 C10 H10 116.9 . . ?
C10 C11 C12 123.6(3) . . ?
C10 C11 H11 118.2 . . ?
C12 C11 H11 118.2 . . ?
C13 C12 C11 124.2(3) . . ?
C13 C12 H12 117.9 . . ?
C11 C12 H12 117.9 . . ?
C12 C13 C14 126.1(4) . . ?
C12 C13 H13 116.9 . . ?
C14 C13 H13 116.9 . . ?
O2 C14 C13 118.1(5) . . ?
O2 C14 C15 121.8(4) . . ?
C13 C14 C15 120.1(4) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 C17 112.9(2) . . ?
N2 C16 H16A 109.0 . . ?
C17 C16 H16A 109.0 . . ?
N2 C16 H16B 109.0 . . ?
C17 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C18 C17 C22 116.4(3) . . ?
C18 C17 C16 121.4(3) . . ?
C22 C17 C16 122.2(3) . . ?
C17 C18 C19 122.7(3) . . ?
C17 C18 H18 118.6 . . ?
C19 C18 H18 118.6 . . ?
C20 C19 C18 120.0(4) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 118.7(3) . . ?
C19 C20 O3 124.8(4) . . ?
C21 C20 O3 116.6(3) . . ?
C20 C21 C22 121.1(3) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C21 C22 C17 121.1(3) . . ?
C21 C22 H22 119.4 . . ?
C17 C22 H22 119.4 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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(4) . . . . ?
C8 C1 C2 C3 179.7(2) . . . . ?
C1 C2 C3 C4 1.2(4) . . . . ?
C1 C2 C3 Cl1 -179.0(2) . . . . ?
C2 C3 C4 C5 -1.3(4) . . . . ?
Cl1 C3 C4 C5 178.9(2) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
C2 C1 C6 N2 178.2(2) . . . . ?
C8 C1 C6 N2 -1.5(4) . . . . ?
C2 C1 C6 C5 -1.3(4) . . . . ?
C8 C1 C6 C5 179.1(2) . . . . ?
C7 N2 C6 C1 -8.7(4) . . . . ?
C16 N2 C6 C1 173.9(2) . . . . ?
C7 N2 C6 C5 170.7(2) . . . . ?
C16 N2 C6 C5 -6.7(4) . . . . ?
C4 C5 C6 C1 1.2(4) . . . . ?
C4 C5 C6 N2 -178.3(3) . . . . ?
C8 N1 C7 O1 -169.8(3) . . . . ?
C8 N1 C7 N2 10.8(4) . . . . ?
C6 N2 C7 O1 -174.7(2) . . . . ?
C16 N2 C7 O1 2.8(4) . . . . ?
C6 N2 C7 N1 4.7(4) . . . . ?
C16 N2 C7 N1 -177.9(2) . . . . ?
C7 N1 C8 C10 -142.5(3) . . . . ?
C7 N1 C8 C1 -19.2(4) . . . . ?
C7 N1 C8 C9 99.6(3) . . . . ?
C2 C1 C8 N1 -166.1(2) . . . . ?
C6 C1 C8 N1 13.5(3) . . . . ?
C2 C1 C8 C10 -42.5(3) . . . . ?
C6 C1 C8 C10 137.1(2) . . . . ?
C2 C1 C8 C9 76.5(3) . . . . ?
C6 C1 C8 C9 -103.9(3) . . . . ?
N1 C8 C9 F3 -61.6(3) . . . . ?
C10 C8 C9 F3 178.3(2) . . . . ?
C1 C8 C9 F3 57.5(3) . . . . ?
N1 C8 C9 F2 177.7(2) . . . . ?
C10 C8 C9 F2 57.5(3) . . . . ?
C1 C8 C9 F2 -63.3(3) . . . . ?
N1 C8 C9 F1 57.4(3) . . . . ?
C10 C8 C9 F1 -62.7(3) . . . . ?
C1 C8 C9 F1 176.5(2) . . . . ?
N1 C8 C10 C11 8.0(4) . . . . ?
C1 C8 C10 C11 -114.7(3) . . . . ?
C9 C8 C10 C11 125.6(3) . . . . ?
C8 C10 C11 C12 174.5(3) . . . . ?
C10 C11 C12 C13 179.7(3) . . . . ?
C11 C12 C13 C14 179.0(3) . . . . ?
C12 C13 C14 O2 176.6(4) . . . . ?
C12 C13 C14 C15 -2.8(7) . . . . ?
C7 N2 C16 C17 109.6(3) . . . . ?
C6 N2 C16 C17 -72.9(3) . . . . ?
N2 C16 C17 C18 -47.3(4) . . . . ?
N2 C16 C17 C22 133.5(3) . . . . ?
C22 C17 C18 C19 0.5(6) . . . . ?
C16 C17 C18 C19 -178.7(4) . . . . ?
C17 C18 C19 C20 0.1(7) . . . . ?
C18 C19 C20 C21 -0.6(6) . . . . ?
C18 C19 C20 O3 179.5(4) . . . . ?
C23 O3 C20 C19 -0.8(6) . . . . ?
C23 O3 C20 C21 179.3(4) . . . . ?
C19 C20 C21 C22 0.5(6) . . . . ?
O3 C20 C21 C22 -179.6(4) . . . . ?
C20 C21 C22 C17 0.1(6) . . . . ?
C18 C17 C22 C21 -0.6(6) . . . . ?
C16 C17 C22 C21 178.6(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 H1 O1 0.832(17) 1.988(18) 2.816(3) 174(3) 5_665
C10 H10 O2 0.93 2.27 3.191(4) 168.4 3_645
N1 H1 O1 0.832(17) 1.988(18) 2.816(3) 174(3) 5_665
C10 H10 O2 0.93 2.27 3.191(4) 168.4 3_645
N1 H1 O1 0.832(17) 1.988(18) 2.816(3) 174(3) 5_665
C10 H10 O2 0.93 2.27 3.191(4) 168.4 3_645
C10 H10 O2 0.93 2.27 3.191(4) 168.4 3_645
N1 H1 O1 0.832(17) 1.988(18) 2.816(3) 174(3) 5_665
C10 H10 O2 0.93 2.27 3.191(4) 168.4 3_645
N1 H1 O1 0.832(17) 1.988(18) 2.816(3) 174(3) 5_665
C10 H10 O2 0.93 2.27 3.191(4) 168.4 3_645
N1 H1 O1 0.832(17) 1.988(18) 2.816(3) 174(3) 5_665
C10 H10 O2 0.93 2.27 3.191(4) 168.4 3_645
N1 H1 O1 0.832(17) 1.988(18) 2.816(3) 174(3) 5_665

_refine_diff_density_max         0.226
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.037

_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_cd214380
_database_code_depnum_ccdc_archive 'CCDC 1011176'
_audit_update_record             
;
2014-06-30 deposited with the CCDC.
2017-09-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H24 N2 O4'
_chemical_formula_weight         356.41

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                   18.416(5)
_cell_length_b                   11.310(3)
_cell_length_c                   9.759(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.907(7)
_cell_angle_gamma                90
_cell_volume                     2027.9(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3014
_cell_measurement_theta_min      5.521
_cell_measurement_theta_max      45.488

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.123
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6440
_exptl_absorpt_correction_T_max  0.7457
_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            12037
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.115
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3975
_reflns_number_gt                2802
_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 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)+(0.0750P)²+0.1507P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3975
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1398
_refine_ls_wR_factor_gt          0.1271
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.002
_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 0.17288(8) 0.42379(13) 0.38474(13) 0.0607(4) Uani 1 1 d . . . . .
N2 N 0.28768(8) 0.30708(12) 0.15079(14) 0.0556(4) Uani 1 1 d . . . . .
O1 O 0.14505(8) 0.25440(12) 0.26412(13) 0.0778(4) Uani 1 1 d . . . . .
O2 O 0.05667(10) 0.64946(14) -0.35403(16) 0.1055(6) Uani 1 1 d . . . . .
O3 O 0.31495(7) 0.25137(10) 0.36957(10) 0.0646(4) Uani 1 1 d . . . . .
O4 O 0.37078(7) 0.17035(10) 0.19179(11) 0.0674(4) Uani 1 1 d . . . . .
C1 C 0.26690(9) 0.49755(14) 0.27010(16) 0.0543(4) Uani 1 1 d . . . . .
C2 C 0.32390(10) 0.57147(16) 0.2500(2) 0.0697(5) Uani 1 1 d . . . . .
H2 H 0.3513 0.5623 0.1741 0.084 Uiso 1 1 calc R U . . .
C3 C 0.34024(13) 0.66095(18) 0.3455(3) 0.0897(7) Uani 1 1 d . . . . .
H3 H 0.3788 0.7121 0.3335 0.108 Uiso 1 1 calc R U . . .
C4 C 0.29991(14) 0.6734(2) 0.4559(3) 0.0927(7) Uani 1 1 d . . . . .
H4 H 0.3113 0.7342 0.5179 0.111 Uiso 1 1 calc R U . . .
C5 C 0.24222(12) 0.59861(19) 0.4798(2) 0.0799(6) Uani 1 1 d . . . . .
H5 H 0.2154 0.6074 0.5566 0.096 Uiso 1 1 calc R U . . .
C6 C 0.22657(10) 0.51069(14) 0.38438(16) 0.0570(4) Uani 1 1 d . . . . .
C7 C 0.17904(9) 0.34561(16) 0.28137(16) 0.0574(4) Uani 1 1 d . . . . .
C8 C 0.23565(9) 0.39655(13) 0.18501(15) 0.0503(4) Uani 1 1 d . . . . .
C9 C 0.19369(9) 0.43470(15) 0.05394(15) 0.0548(4) Uani 1 1 d . . . . .
H9 H 0.1815 0.3759 -0.0101 0.066 Uiso 1 1 calc R U . . .
C10 C 0.17275(9) 0.54272(16) 0.02161(16) 0.0592(4) Uani 1 1 d . . . . .
H10 H 0.1856 0.6027 0.0838 0.071 Uiso 1 1 calc R U . . .
C11 C 0.13124(9) 0.57508(16) -0.10332(17) 0.0596(4) Uani 1 1 d . . . . .
H11 H 0.1226 0.5170 -0.1699 0.072 Uiso 1 1 calc R U . . .
C12 C 0.10437(10) 0.68277(16) -0.12989(18) 0.0673(5) Uani 1 1 d . . . . .
H12 H 0.1129 0.7408 -0.0631 0.081 Uiso 1 1 calc R U . . .
C13 C 0.06250(10) 0.71598(17) -0.25660(19) 0.0669(5) Uani 1 1 d . . . . .
C14 C 0.02806(11) 0.83448(17) -0.2621(2) 0.0810(6) Uani 1 1 d . . . . .
H14A H 0.0066 0.8487 -0.3530 0.121 Uiso 1 1 calc R U . . .
H14B H 0.0643 0.8937 -0.2392 0.121 Uiso 1 1 calc R U . . .
H14C H -0.0090 0.8378 -0.1975 0.121 Uiso 1 1 calc R U . . .
C15 C 0.12318(12) 0.40847(19) 0.49236(19) 0.0821(6) Uani 1 1 d . . . . .
H15A H 0.0886 0.3478 0.4662 0.123 Uiso 1 1 calc R U . . .
H15B H 0.0980 0.4814 0.5061 0.123 Uiso 1 1 calc R U . . .
H15C H 0.1501 0.3861 0.5761 0.123 Uiso 1 1 calc R U . . .
C16 C 0.32373(9) 0.24278(13) 0.24858(15) 0.0521(4) Uani 1 1 d . . . . .
C17 C 0.41702(10) 0.08928(16) 0.27432(19) 0.0681(5) Uani 1 1 d . . . . .
C18 C 0.45912(13) 0.0287(2) 0.1662(3) 0.1002(8) Uani 1 1 d . . . . .
H18A H 0.4258 -0.0119 0.1024 0.150 Uiso 1 1 calc R U . . .
H18B H 0.4926 -0.0271 0.2096 0.150 Uiso 1 1 calc R U . . .
H18C H 0.4856 0.0868 0.1180 0.150 Uiso 1 1 calc R U . . .
C19 C 0.46699(13) 0.1580(2) 0.3751(3) 0.1072(8) Uani 1 1 d . . . . .
H19A H 0.4920 0.2178 0.3269 0.161 Uiso 1 1 calc R U . . .
H19B H 0.5018 0.1051 0.4199 0.161 Uiso 1 1 calc R U . . .
H19C H 0.4388 0.1946 0.4426 0.161 Uiso 1 1 calc R U . . .
C20 C 0.37013(14) 0.00172(19) 0.3446(3) 0.0976(7) Uani 1 1 d . . . . .
H20A H 0.3455 0.0412 0.4152 0.146 Uiso 1 1 calc R U . . .
H20B H 0.4002 -0.0603 0.3848 0.146 Uiso 1 1 calc R U . . .
H20C H 0.3349 -0.0315 0.2785 0.146 Uiso 1 1 calc R U . . .
H2A H 0.2920(9) 0.2934(15) 0.0709(19) 0.055(5) 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 C7 1.352(2) . ?
N1 C6 1.394(2) . ?
N1 C15 1.450(2) . ?
N2 C16 1.339(2) . ?
N2 C8 1.448(2) . ?
N2 H2A 0.804(18) . ?
O1 C7 1.212(2) . ?
O2 C13 1.211(2) . ?
O3 C16 1.2065(17) . ?
O4 C16 1.3396(18) . ?
O4 C17 1.456(2) . ?
C1 C2 1.366(2) . ?
C1 C6 1.389(2) . ?
C1 C8 1.503(2) . ?
C2 C3 1.394(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.357(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(2) . ?
C5 H5 0.9300 . ?
C7 C8 1.561(2) . ?
C8 C9 1.511(2) . ?
C9 C10 1.313(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.441(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.333(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.461(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.482(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C17 C20 1.509(3) . ?
C17 C19 1.515(3) . ?
C17 C18 1.515(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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 N1 C6 111.32(13) . . ?
C7 N1 C15 123.48(16) . . ?
C6 N1 C15 124.67(15) . . ?
C16 N2 C8 121.25(13) . . ?
C16 N2 H2A 120.6(12) . . ?
C8 N2 H2A 118.0(12) . . ?
C16 O4 C17 121.77(12) . . ?
C2 C1 C6 120.50(16) . . ?
C2 C1 C8 130.89(15) . . ?
C6 C1 C8 108.61(14) . . ?
C1 C2 C3 118.76(19) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 120.1(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 122.4(2) . . ?
C3 C4 H4 118.8 . . ?
C5 C4 H4 118.8 . . ?
C6 C5 C4 116.89(19) . . ?
C6 C5 H5 121.6 . . ?
C4 C5 H5 121.6 . . ?
C5 C6 C1 121.38(18) . . ?
C5 C6 N1 128.46(17) . . ?
C1 C6 N1 110.15(14) . . ?
O1 C7 N1 126.25(15) . . ?
O1 C7 C8 126.16(14) . . ?
N1 C7 C8 107.55(15) . . ?
N2 C8 C1 115.07(14) . . ?
N2 C8 C9 108.21(12) . . ?
C1 C8 C9 113.88(13) . . ?
N2 C8 C7 111.14(12) . . ?
C1 C8 C7 101.18(12) . . ?
C9 C8 C7 106.94(13) . . ?
C10 C9 C8 126.43(15) . . ?
C10 C9 H9 116.8 . . ?
C8 C9 H9 116.8 . . ?
C9 C10 C11 124.73(16) . . ?
C9 C10 H10 117.6 . . ?
C11 C10 H10 117.6 . . ?
C12 C11 C10 124.39(17) . . ?
C12 C11 H11 117.8 . . ?
C10 C11 H11 117.8 . . ?
C11 C12 C13 124.53(17) . . ?
C11 C12 H12 117.7 . . ?
C13 C12 H12 117.7 . . ?
O2 C13 C12 121.20(17) . . ?
O2 C13 C14 121.23(18) . . ?
C12 C13 C14 117.57(17) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O3 C16 N2 124.09(14) . . ?
O3 C16 O4 125.99(15) . . ?
N2 C16 O4 109.91(13) . . ?
O4 C17 C20 109.47(16) . . ?
O4 C17 C19 110.04(16) . . ?
C20 C17 C19 112.49(19) . . ?
O4 C17 C18 101.95(15) . . ?
C20 C17 C18 110.84(18) . . ?
C19 C17 C18 111.54(18) . . ?
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 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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 -0.7(3) . . . . ?
C8 C1 C2 C3 178.46(17) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
C4 C5 C6 N1 178.97(17) . . . . ?
C2 C1 C6 C5 0.6(3) . . . . ?
C8 C1 C6 C5 -178.78(15) . . . . ?
C2 C1 C6 N1 -178.40(14) . . . . ?
C8 C1 C6 N1 2.27(18) . . . . ?
C7 N1 C6 C5 -173.55(17) . . . . ?
C15 N1 C6 C5 -1.7(3) . . . . ?
C7 N1 C6 C1 5.31(19) . . . . ?
C15 N1 C6 C1 177.16(15) . . . . ?
C6 N1 C7 O1 171.99(17) . . . . ?
C15 N1 C7 O1 0.0(3) . . . . ?
C6 N1 C7 C8 -10.21(18) . . . . ?
C15 N1 C7 C8 177.82(15) . . . . ?
C16 N2 C8 C1 62.85(19) . . . . ?
C16 N2 C8 C9 -168.51(15) . . . . ?
C16 N2 C8 C7 -51.4(2) . . . . ?
C2 C1 C8 N2 53.2(2) . . . . ?
C6 C1 C8 N2 -127.53(14) . . . . ?
C2 C1 C8 C9 -72.5(2) . . . . ?
C6 C1 C8 C9 106.71(15) . . . . ?
C2 C1 C8 C7 173.12(17) . . . . ?
C6 C1 C8 C7 -7.64(16) . . . . ?
O1 C7 C8 N2 -48.8(2) . . . . ?
N1 C7 C8 N2 133.37(14) . . . . ?
O1 C7 C8 C1 -171.48(17) . . . . ?
N1 C7 C8 C1 10.72(16) . . . . ?
O1 C7 C8 C9 69.1(2) . . . . ?
N1 C7 C8 C9 -108.73(15) . . . . ?
N2 C8 C9 C10 -141.39(17) . . . . ?
C1 C8 C9 C10 -12.1(2) . . . . ?
C7 C8 C9 C10 98.81(19) . . . . ?
C8 C9 C10 C11 -178.45(14) . . . . ?
C9 C10 C11 C12 173.46(18) . . . . ?
C10 C11 C12 C13 179.77(16) . . . . ?
C11 C12 C13 O2 -8.8(3) . . . . ?
C11 C12 C13 C14 171.81(17) . . . . ?
C8 N2 C16 O3 1.9(3) . . . . ?
C8 N2 C16 O4 -177.19(13) . . . . ?
C17 O4 C16 O3 1.4(3) . . . . ?
C17 O4 C16 N2 -179.53(14) . . . . ?
C16 O4 C17 C20 62.6(2) . . . . ?
C16 O4 C17 C19 -61.5(2) . . . . ?
C16 O4 C17 C18 -179.95(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O3 0.804(18) 2.100(19) 2.8998(19) 173.4(16) 4_565
C20 H20A O3 0.96 2.48 3.016(3) 115.5 .
C19 H19C O3 0.96 2.43 2.990(3) 117.0 .
C15 H15C O1 0.96 2.43 3.232(2) 140.3 4_566
C15 H15B O2 0.96 2.49 3.380(3) 154.3 1_556
C12 H12 O2 0.93 2.66 3.456(3) 144.2 4_576

_refine_diff_density_max         0.199
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.034

_shelxl_version_number           2013-4



