# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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. 
# 
#######################################################################

data_sa4456
_database_code_depnum_ccdc_archive 'CCDC 1474966'
_audit_update_record             
;
2017-01-03 deposited with the CCDC.
2017-05-30 downloaded from the CCDC.
;
_audit_creation_date             2015-12-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C23 H20 N2 O4'
_chemical_formula_sum            'C23 H20 N2 O4'
_chemical_formula_weight         388.41
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5462(17)
_cell_length_b                   9.7412(19)
_cell_length_c                   12.085(2)
_cell_angle_alpha                90.29(3)
_cell_angle_beta                 104.04(3)
_cell_angle_gamma                94.61(3)
_cell_volume                     972.6(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3167
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4835
_cell_measurement_theta_min      1.7376
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10072
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.490
_diffrn_reflns_theta_min         2.465
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 40.0859
	          2theta: -20.0605
scan:
	Number of images: 274
	           Slice: -81.0000 - 56.0000
	     Image width: 0.5000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 40.0859
	          2theta: -20.0605
scan:
	Number of images: 244
	           Slice: -107.0000 - 15.0000
	     Image width: 0.5000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 40.0859
	          2theta: -20.0605
;
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             4388
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0255
_diffrn_orient_matrix_UB_12      -0.1134
_diffrn_orient_matrix_UB_13      0.0338
_diffrn_orient_matrix_UB_21      -0.0509
_diffrn_orient_matrix_UB_22      -0.0440
_diffrn_orient_matrix_UB_23      -0.0781
_diffrn_orient_matrix_UB_31      0.0730
_diffrn_orient_matrix_UB_32      -0.0178
_diffrn_orient_matrix_UB_33      -0.0404
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3937
_reflns_number_total             4384
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2013)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2013)'
_computing_structure_solution    
;
 'XS (Sheldrick, 2013)'
;
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4384
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0644
_refine_ls_restrained_S_all      1.152
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0438P)²+0.5336P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1352
_refine_ls_wR_factor_ref         0.1425
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C19(H19),
 C20(H20), C21(H21), C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.50889(17) 0.07466(15) 0.36195(12) 0.0373(3) Uani 1 1 d . . . . .
O2 O 0.5770(2) -0.1442(2) 0.04856(14) 0.0602(5) Uani 1 1 d . . . . .
O3 O 0.15445(16) -0.30056(14) 0.19128(11) 0.0321(3) Uani 1 1 d . . . . .
O4 O 0.10186(17) -0.18283(16) 0.51236(12) 0.0392(4) Uani 1 1 d . . . . .
N1 N 0.54889(19) -0.03762(18) 0.20866(14) 0.0333(4) Uani 1 1 d . . . . .
N2 N 0.36785(19) -0.22619(17) 0.12095(13) 0.0298(4) Uani 1 1 d . . . . .
C1 C 0.5035(2) -0.1373(2) 0.12182(17) 0.0361(5) Uani 1 1 d . . . . .
C2 C 0.2787(2) -0.22633(18) 0.20200(15) 0.0246(4) Uani 1 1 d . . . . .
C3 C 0.3495(2) -0.13870(19) 0.30856(15) 0.0244(4) Uani 1 1 d . . . . .
C4 C 0.4716(2) -0.02216(19) 0.29514(15) 0.0278(4) Uani 1 1 d . . . . .
C5 C 0.6884(3) 0.0598(3) 0.2062(2) 0.0538(7) Uani 1 1 d . . . . .
H5A H 0.7708 0.0113 0.1853 0.081 Uiso 1 1 calc GR . . . .
H5B H 0.7306 0.1025 0.2803 0.081 Uiso 1 1 calc GR . . . .
H5C H 0.6550 0.1292 0.1513 0.081 Uiso 1 1 calc GR . . . .
C6 C 0.3210(3) -0.3322(2) 0.02888(18) 0.0412(5) Uani 1 1 d . . . . .
H6A H 0.2306 -0.3048 -0.0284 0.062 Uiso 1 1 calc GR . . . .
H6B H 0.2913 -0.4183 0.0596 0.062 Uiso 1 1 calc GR . . . .
H6C H 0.4106 -0.3424 -0.0046 0.062 Uiso 1 1 calc GR . . . .
C7 C 0.4452(2) -0.2384(2) 0.40363(15) 0.0278(4) Uani 1 1 d . . . . .
H7 H 0.5213 -0.1790 0.4614 0.033 Uiso 1 1 calc R . . . .
C8 C 0.3137(2) -0.3001(2) 0.45923(17) 0.0322(4) Uani 1 1 d . . . . .
H8A H 0.2586 -0.3828 0.4178 0.039 Uiso 1 1 calc R . . . .
H8B H 0.3601 -0.3232 0.5377 0.039 Uiso 1 1 calc R . . . .
C9 C 0.1986(2) -0.1902(2) 0.45406(16) 0.0295(4) Uani 1 1 d . . . . .
C10 C 0.2194(2) -0.09247(19) 0.36311(15) 0.0265(4) Uani 1 1 d . . . . .
C11 C 0.1325(2) 0.0165(2) 0.34251(16) 0.0293(4) Uani 1 1 d . . . . .
H11 H 0.0660 0.0290 0.3916 0.035 Uiso 1 1 calc R . . . .
C12 C 0.1266(2) 0.1197(2) 0.25359(17) 0.0303(4) Uani 1 1 d . . . . .
C13 C 0.0952(2) 0.2537(2) 0.27648(19) 0.0359(5) Uani 1 1 d . . . . .
H13 H 0.0791 0.2767 0.3474 0.043 Uiso 1 1 calc R . . . .
C14 C 0.0879(3) 0.3529(2) 0.1939(2) 0.0431(5) Uani 1 1 d . . . . .
H14 H 0.0697 0.4428 0.2104 0.052 Uiso 1 1 calc R . . . .
C15 C 0.1074(3) 0.3189(3) 0.0871(2) 0.0472(6) Uani 1 1 d . . . . .
H15 H 0.1028 0.3860 0.0322 0.057 Uiso 1 1 calc R . . . .
C16 C 0.1338(3) 0.1860(3) 0.0617(2) 0.0475(6) Uani 1 1 d . . . . .
H16 H 0.1448 0.1628 -0.0106 0.057 Uiso 1 1 calc R . . . .
C17 C 0.1439(3) 0.0868(2) 0.14483(19) 0.0417(5) Uani 1 1 d . . . . .
H17 H 0.1625 -0.0028 0.1278 0.050 Uiso 1 1 calc R . . . .
C18 C 0.5435(2) -0.3374(2) 0.35800(16) 0.0311(4) Uani 1 1 d . . . . .
C19 C 0.7048(3) -0.2994(3) 0.3606(2) 0.0461(6) Uani 1 1 d . . . . .
H19 H 0.7537 -0.2163 0.3955 0.055 Uiso 1 1 calc R . . . .
C20 C 0.7935(3) -0.3849(3) 0.3115(2) 0.0635(8) Uani 1 1 d . . . . .
H20 H 0.9010 -0.3584 0.3130 0.076 Uiso 1 1 calc R . . . .
C21 C 0.7223(3) -0.5088(3) 0.2607(2) 0.0587(7) Uani 1 1 d . . . . .
H21 H 0.7815 -0.5655 0.2274 0.070 Uiso 1 1 calc R . . . .
C22 C 0.5646(3) -0.5486(2) 0.25902(19) 0.0454(6) Uani 1 1 d . . . . .
H22 H 0.5169 -0.6325 0.2251 0.055 Uiso 1 1 calc R . . . .
C23 C 0.4756(3) -0.4637(2) 0.30794(17) 0.0359(5) Uani 1 1 d . . . . .
H23 H 0.3688 -0.4920 0.3072 0.043 Uiso 1 1 calc R . . . .


_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 C4 1.209(2) . ?
O2 C1 1.208(2) . ?
O3 C2 1.215(2) . ?
O4 C9 1.215(2) . ?
N1 C1 1.388(3) . ?
N1 C4 1.378(2) . ?
N1 C5 1.469(3) . ?
N2 C1 1.388(3) . ?
N2 C2 1.379(2) . ?
N2 C6 1.473(2) . ?
C2 C3 1.510(2) . ?
C3 C4 1.516(3) . ?
C3 C7 1.617(3) . ?
C3 C10 1.519(2) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7 0.9800 . ?
C7 C8 1.529(3) . ?
C7 C18 1.513(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.503(3) . ?
C9 C10 1.491(3) . ?
C10 C11 1.334(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.469(3) . ?
C12 C13 1.393(3) . ?
C12 C17 1.397(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.387(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.383(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.377(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.390(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.390(3) . ?
C18 C23 1.388(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.392(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.377(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.368(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.387(3) . ?
C23 H23 0.9300 . ?

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 C5 116.95(17) . . ?
C4 N1 C1 125.01(16) . . ?
C4 N1 C5 118.04(17) . . ?
C1 N2 C6 116.95(16) . . ?
C2 N2 C1 125.03(16) . . ?
C2 N2 C6 117.95(16) . . ?
O2 C1 N1 121.25(19) . . ?
O2 C1 N2 121.44(19) . . ?
N2 C1 N1 117.29(16) . . ?
O3 C2 N2 121.31(16) . . ?
O3 C2 C3 121.63(16) . . ?
N2 C2 C3 116.89(15) . . ?
C2 C3 C4 114.68(15) . . ?
C2 C3 C7 106.99(14) . . ?
C2 C3 C10 112.01(14) . . ?
C4 C3 C7 106.46(14) . . ?
C4 C3 C10 113.19(15) . . ?
C10 C3 C7 102.38(14) . . ?
O1 C4 N1 121.25(17) . . ?
O1 C4 C3 121.89(17) . . ?
N1 C4 C3 116.63(16) . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C3 C7 H7 107.1 . . ?
C8 C7 C3 103.46(14) . . ?
C8 C7 H7 107.1 . . ?
C18 C7 C3 114.05(15) . . ?
C18 C7 H7 107.1 . . ?
C18 C7 C8 117.47(16) . . ?
C7 C8 H8A 110.7 . . ?
C7 C8 H8B 110.7 . . ?
H8A C8 H8B 108.8 . . ?
C9 C8 C7 105.35(15) . . ?
C9 C8 H8A 110.7 . . ?
C9 C8 H8B 110.7 . . ?
O4 C9 C8 126.04(18) . . ?
O4 C9 C10 125.21(18) . . ?
C10 C9 C8 108.73(15) . . ?
C9 C10 C3 109.08(15) . . ?
C11 C10 C3 130.27(17) . . ?
C11 C10 C9 120.64(17) . . ?
C10 C11 H11 115.3 . . ?
C10 C11 C12 129.50(17) . . ?
C12 C11 H11 115.3 . . ?
C13 C12 C11 119.06(18) . . ?
C13 C12 C17 118.56(19) . . ?
C17 C12 C11 122.32(18) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.3(2) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.3(2) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.3(2) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 120.2 . . ?
C15 C16 C17 119.6(2) . . ?
C17 C16 H16 120.2 . . ?
C12 C17 H17 119.5 . . ?
C16 C17 C12 120.9(2) . . ?
C16 C17 H17 119.5 . . ?
C19 C18 C7 119.77(19) . . ?
C23 C18 C7 121.90(18) . . ?
C23 C18 C19 118.25(19) . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.5(2) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 120.1(2) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.1(2) . . ?
C22 C21 H21 119.9 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 120.0(2) . . ?
C23 C22 H22 120.0 . . ?
C18 C23 H23 119.5 . . ?
C22 C23 C18 121.0(2) . . ?
C22 C23 H23 119.5 . . ?

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
O3 C2 C3 C4 -162.13(16) . . . . ?
O3 C2 C3 C7 80.1(2) . . . . ?
O3 C2 C3 C10 -31.4(2) . . . . ?
O4 C9 C10 C3 -178.79(18) . . . . ?
O4 C9 C10 C11 2.5(3) . . . . ?
N2 C2 C3 C4 22.6(2) . . . . ?
N2 C2 C3 C7 -95.20(18) . . . . ?
N2 C2 C3 C10 153.38(16) . . . . ?
C1 N1 C4 O1 -173.2(2) . . . . ?
C1 N1 C4 C3 12.2(3) . . . . ?
C1 N2 C2 O3 174.58(19) . . . . ?
C1 N2 C2 C3 -10.1(3) . . . . ?
C2 N2 C1 O2 179.1(2) . . . . ?
C2 N2 C1 N1 -2.6(3) . . . . ?
C2 C3 C4 O1 161.92(17) . . . . ?
C2 C3 C4 N1 -23.6(2) . . . . ?
C2 C3 C7 C8 -86.66(16) . . . . ?
C2 C3 C7 C18 42.1(2) . . . . ?
C2 C3 C10 C9 95.05(18) . . . . ?
C2 C3 C10 C11 -86.4(2) . . . . ?
C3 C7 C8 C9 -31.98(18) . . . . ?
C3 C7 C18 C19 91.3(2) . . . . ?
C3 C7 C18 C23 -85.5(2) . . . . ?
C3 C10 C11 C12 5.7(3) . . . . ?
C4 N1 C1 O2 179.7(2) . . . . ?
C4 N1 C1 N2 1.4(3) . . . . ?
C4 C3 C7 C8 150.28(15) . . . . ?
C4 C3 C7 C18 -80.94(19) . . . . ?
C4 C3 C10 C9 -133.41(16) . . . . ?
C4 C3 C10 C11 45.1(3) . . . . ?
C5 N1 C1 O2 0.9(3) . . . . ?
C5 N1 C1 N2 -177.5(2) . . . . ?
C5 N1 C4 O1 5.7(3) . . . . ?
C5 N1 C4 C3 -168.88(19) . . . . ?
C6 N2 C1 O2 2.0(3) . . . . ?
C6 N2 C1 N1 -179.68(19) . . . . ?
C6 N2 C2 O3 -8.4(3) . . . . ?
C6 N2 C2 C3 166.91(17) . . . . ?
C7 C3 C4 O1 -80.0(2) . . . . ?
C7 C3 C4 N1 94.53(18) . . . . ?
C7 C3 C10 C9 -19.24(18) . . . . ?
C7 C3 C10 C11 159.32(19) . . . . ?
C7 C8 C9 O4 -160.46(19) . . . . ?
C7 C8 C9 C10 20.9(2) . . . . ?
C7 C18 C19 C20 -175.3(2) . . . . ?
C7 C18 C23 C22 175.16(19) . . . . ?
C8 C7 C18 C19 -147.4(2) . . . . ?
C8 C7 C18 C23 35.8(3) . . . . ?
C8 C9 C10 C3 -0.1(2) . . . . ?
C8 C9 C10 C11 -178.87(17) . . . . ?
C9 C10 C11 C12 -175.86(18) . . . . ?
C10 C3 C4 O1 31.7(2) . . . . ?
C10 C3 C4 N1 -153.78(16) . . . . ?
C10 C3 C7 C8 31.26(17) . . . . ?
C10 C3 C7 C18 160.03(15) . . . . ?
C10 C11 C12 C13 -149.1(2) . . . . ?
C10 C11 C12 C17 33.8(3) . . . . ?
C11 C12 C13 C14 -179.60(17) . . . . ?
C11 C12 C17 C16 178.44(19) . . . . ?
C12 C13 C14 C15 1.7(3) . . . . ?
C13 C12 C17 C16 1.4(3) . . . . ?
C13 C14 C15 C16 0.2(3) . . . . ?
C14 C15 C16 C17 -1.3(3) . . . . ?
C15 C16 C17 C12 0.5(3) . . . . ?
C17 C12 C13 C14 -2.5(3) . . . . ?
C18 C7 C8 C9 -158.62(16) . . . . ?
C18 C19 C20 C21 -0.6(4) . . . . ?
C19 C18 C23 C22 -1.7(3) . . . . ?
C19 C20 C21 C22 -0.5(5) . . . . ?
C20 C21 C22 C23 0.4(4) . . . . ?
C21 C22 C23 C18 0.7(3) . . . . ?
C23 C18 C19 C20 1.6(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mx4727
_database_code_depnum_ccdc_archive 'CCDC 1525361'
_audit_update_record             
;
2017-01-03 deposited with the CCDC.
2017-05-30 downloaded from the CCDC.
;
_audit_creation_date             2016-04-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H20 N2 O4'
_chemical_formula_sum            'C23 H20 N2 O4'
_chemical_formula_weight         388.41
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.989(4)
_cell_length_b                   5.730(3)
_cell_length_c                   36.156(16)
_cell_angle_alpha                90
_cell_angle_beta                 96.682(6)
_cell_angle_gamma                90
_cell_volume                     1849.6(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5200
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.3
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.815
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    "'not measured'"
_exptl_crystal_description       rod
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1260
_diffrn_reflns_av_unetI/netI     0.0783
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            15481
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         1.134
_diffrn_ambient_temperature      173
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 50.0502
	          2theta: -19.9269
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 50.0502
	          2theta: -19.9269
scan:
	Number of images: 120
	           Slice: -110.0000 - -50.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 50.0502
	          2theta: -19.9269
;
_diffrn_measurement_device       
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.033175
_diffrn_orient_matrix_UB_12      0.059513
_diffrn_orient_matrix_UB_13      0.088898
_diffrn_orient_matrix_UB_21      -0.054549
_diffrn_orient_matrix_UB_22      -0.127638
_diffrn_orient_matrix_UB_23      0.105804
_diffrn_orient_matrix_UB_31      0.025922
_diffrn_orient_matrix_UB_32      -0.010105
_diffrn_orient_matrix_UB_33      0.001174
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   "Rotating Anode'"
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3893
_reflns_number_total             4233
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2014)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.181
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4233
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0714
_refine_ls_restrained_S_all      1.181
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0428P)²+1.2837P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1666
_refine_ls_wR_factor_ref         0.1711
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C19(H19), C20(H20),
 C21(H21), C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.0358(2) 0.4771(3) 0.69604(5) 0.0382(4) Uani 1 1 d . . . . .
O2 O 0.23166(19) 1.1131(3) 0.66867(5) 0.0350(4) Uani 1 1 d . . . . .
O3 O 0.06856(19) 0.5679(3) 0.57742(4) 0.0363(4) Uani 1 1 d . . . . .
O4 O 0.54151(18) 0.3402(3) 0.58969(5) 0.0333(4) Uani 1 1 d . . . . .
N1 N 0.1040(2) 0.7919(3) 0.68355(5) 0.0277(4) Uani 1 1 d . . . . .
N2 N 0.0103(2) 0.5265(3) 0.63620(5) 0.0280(4) Uani 1 1 d . . . . .
C1 C 0.0247(2) 0.5885(4) 0.67363(6) 0.0274(5) Uani 1 1 d . . . . .
C2 C 0.1819(2) 0.9215(4) 0.65981(6) 0.0261(4) Uani 1 1 d . . . . .
C3 C 0.2084(2) 0.8045(4) 0.62356(6) 0.0241(4) Uani 1 1 d . . . . .
C4 C 0.0894(2) 0.6283(4) 0.60973(6) 0.0253(4) Uani 1 1 d . . . . .
C5 C 0.0949(3) 0.8837(5) 0.72122(6) 0.0378(6) Uani 1 1 d . . . . .
H5A H 0.0089 0.8187 0.7309 0.057 Uiso 1 1 calc GR . . . .
H5B H 0.0860 1.0506 0.7202 0.057 Uiso 1 1 calc GR . . . .
H5C H 0.1838 0.8415 0.7371 0.057 Uiso 1 1 calc GR . . . .
C6 C -0.0944(3) 0.3357(5) 0.62474(7) 0.0389(6) Uani 1 1 d . . . . .
H6A H -0.0563 0.1922 0.6358 0.058 Uiso 1 1 calc GR . . . .
H6B H -0.1051 0.3211 0.5981 0.058 Uiso 1 1 calc GR . . . .
H6C H -0.1902 0.3691 0.6328 0.058 Uiso 1 1 calc GR . . . .
C7 C 0.2307(3) 0.9815(4) 0.59241(6) 0.0296(5) Uani 1 1 d . . . . .
H7A H 0.1402 0.9966 0.5751 0.035 Uiso 1 1 calc R . . . .
H7B H 0.2581 1.1338 0.6028 0.035 Uiso 1 1 calc R . . . .
C8 C 0.3554(2) 0.8796(4) 0.57350(6) 0.0256(4) Uani 1 1 d . . . . .
H8 H 0.3830 0.9348 0.5511 0.031 Uiso 1 1 calc R . . . .
C9 C 0.4222(2) 0.7016(4) 0.59224(6) 0.0236(4) Uani 1 1 d . . . . .
C10 C 0.3616(2) 0.6566(4) 0.62900(6) 0.0227(4) Uani 1 1 d . . . . .
H10 H 0.3378 0.4904 0.6309 0.027 Uiso 1 1 calc R . . . .
C11 C 0.4718(2) 0.7267(4) 0.66216(6) 0.0238(4) Uani 1 1 d . . . . .
C12 C 0.4825(3) 0.5919(4) 0.69436(6) 0.0297(5) Uani 1 1 d . . . . .
H12 H 0.4233 0.4593 0.6952 0.036 Uiso 1 1 calc R . . . .
C13 C 0.5808(3) 0.6537(5) 0.72531(7) 0.0357(5) Uani 1 1 d . . . . .
H13 H 0.5859 0.5640 0.7469 0.043 Uiso 1 1 calc R . . . .
C14 C 0.6713(3) 0.8486(5) 0.72417(7) 0.0357(5) Uani 1 1 d . . . . .
H14 H 0.7391 0.8876 0.7447 0.043 Uiso 1 1 calc R . . . .
C15 C 0.6603(3) 0.9851(4) 0.69232(7) 0.0357(5) Uani 1 1 d . . . . .
H15 H 0.7194 1.1180 0.6917 0.043 Uiso 1 1 calc R . . . .
C16 C 0.5619(3) 0.9248(4) 0.66143(6) 0.0308(5) Uani 1 1 d . . . . .
H16 H 0.5557 1.0168 0.6401 0.037 Uiso 1 1 calc R . . . .
C17 C 0.5343(2) 0.5437(4) 0.57911(6) 0.0242(4) Uani 1 1 d . . . . .
C18 C 0.6363(2) 0.6294(4) 0.55229(6) 0.0254(4) Uani 1 1 d . . . . .
C19 C 0.6740(2) 0.4799(4) 0.52461(6) 0.0300(5) Uani 1 1 d . . . . .
H19 H 0.6306 0.3326 0.5221 0.036 Uiso 1 1 calc R . . . .
C20 C 0.7754(3) 0.5483(5) 0.50078(7) 0.0370(6) Uani 1 1 d . . . . .
H20 H 0.7985 0.4486 0.4820 0.044 Uiso 1 1 calc R . . . .
C21 C 0.8423(3) 0.7646(5) 0.50500(7) 0.0380(6) Uani 1 1 d . . . . .
H21 H 0.9122 0.8092 0.4893 0.046 Uiso 1 1 calc R . . . .
C22 C 0.8062(3) 0.9152(4) 0.53232(7) 0.0369(6) Uani 1 1 d . . . . .
H22 H 0.8523 1.0604 0.5351 0.044 Uiso 1 1 calc R . . . .
C23 C 0.7007(2) 0.8505(4) 0.55586(7) 0.0316(5) Uani 1 1 d . . . . .
H23 H 0.6737 0.9540 0.5737 0.038 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.209(3) . ?
O2 C2 1.214(3) . ?
O3 C4 1.212(3) . ?
O4 C17 1.227(3) . ?
N1 C1 1.391(3) . ?
N1 C2 1.385(3) . ?
N1 C5 1.471(3) . ?
N2 C1 1.391(3) . ?
N2 C4 1.386(3) . ?
N2 C6 1.470(3) . ?
C2 C3 1.515(3) . ?
C3 C4 1.513(3) . ?
C3 C7 1.546(3) . ?
C3 C10 1.609(3) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.498(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.329(3) . ?
C9 C10 1.516(3) . ?
C9 C17 1.473(3) . ?
C10 H10 0.9800 . ?
C10 C11 1.517(3) . ?
C11 C12 1.391(3) . ?
C11 C16 1.397(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.389(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.385(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.386(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.386(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.493(3) . ?
C18 C19 1.389(3) . ?
C18 C23 1.393(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.382(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.378(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.378(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.396(3) . ?
C23 H23 0.9300 . ?

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 C5 117.15(18) . . ?
C2 N1 C1 124.75(18) . . ?
C2 N1 C5 117.96(19) . . ?
C1 N2 C6 116.66(19) . . ?
C4 N2 C1 124.54(19) . . ?
C4 N2 C6 118.79(19) . . ?
O1 C1 N1 121.7(2) . . ?
O1 C1 N2 121.3(2) . . ?
N2 C1 N1 116.89(19) . . ?
O2 C2 N1 121.2(2) . . ?
O2 C2 C3 122.5(2) . . ?
N1 C2 C3 116.16(19) . . ?
C2 C3 C7 112.76(18) . . ?
C2 C3 C10 110.22(17) . . ?
C4 C3 C2 113.86(17) . . ?
C4 C3 C7 110.08(18) . . ?
C4 C3 C10 104.52(17) . . ?
C7 C3 C10 104.68(16) . . ?
O3 C4 N2 120.7(2) . . ?
O3 C4 C3 122.23(19) . . ?
N2 C4 C3 116.92(18) . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C3 C7 H7A 110.9 . . ?
C3 C7 H7B 110.9 . . ?
H7A C7 H7B 109.0 . . ?
C8 C7 C3 104.12(17) . . ?
C8 C7 H7A 110.9 . . ?
C8 C7 H7B 110.9 . . ?
C7 C8 H8 123.7 . . ?
C9 C8 C7 112.61(19) . . ?
C9 C8 H8 123.7 . . ?
C8 C9 C10 112.98(18) . . ?
C8 C9 C17 126.34(19) . . ?
C17 C9 C10 120.48(18) . . ?
C3 C10 H10 109.3 . . ?
C9 C10 C3 101.10(16) . . ?
C9 C10 H10 109.3 . . ?
C9 C10 C11 112.32(17) . . ?
C11 C10 C3 115.31(17) . . ?
C11 C10 H10 109.3 . . ?
C12 C11 C10 119.31(19) . . ?
C12 C11 C16 118.9(2) . . ?
C16 C11 C10 121.79(19) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.5(2) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.2(2) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 120.2 . . ?
C13 C14 C15 119.6(2) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.4(2) . . ?
C16 C15 H15 119.8 . . ?
C11 C16 H16 119.8 . . ?
C15 C16 C11 120.3(2) . . ?
C15 C16 H16 119.8 . . ?
O4 C17 C9 119.76(19) . . ?
O4 C17 C18 120.06(19) . . ?
C9 C17 C18 120.17(18) . . ?
C19 C18 C17 119.0(2) . . ?
C19 C18 C23 119.6(2) . . ?
C23 C18 C17 121.26(19) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.6(2) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 120.1 . . ?
C21 C20 C19 119.8(2) . . ?
C21 C20 H20 120.1 . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.4(2) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C23 120.3(2) . . ?
C23 C22 H22 119.9 . . ?
C18 C23 C22 119.3(2) . . ?
C18 C23 H23 120.4 . . ?
C22 C23 H23 120.4 . . ?

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
O2 C2 C3 C4 -154.8(2) . . . . ?
O2 C2 C3 C7 -28.4(3) . . . . ?
O2 C2 C3 C10 88.2(2) . . . . ?
O4 C17 C18 C19 35.9(3) . . . . ?
O4 C17 C18 C23 -140.4(2) . . . . ?
N1 C2 C3 C4 28.6(3) . . . . ?
N1 C2 C3 C7 155.00(19) . . . . ?
N1 C2 C3 C10 -88.4(2) . . . . ?
C1 N1 C2 O2 170.0(2) . . . . ?
C1 N1 C2 C3 -13.4(3) . . . . ?
C1 N2 C4 O3 -178.5(2) . . . . ?
C1 N2 C4 C3 5.3(3) . . . . ?
C2 N1 C1 O1 176.7(2) . . . . ?
C2 N1 C1 N2 -7.2(3) . . . . ?
C2 C3 C4 O3 158.9(2) . . . . ?
C2 C3 C4 N2 -25.0(3) . . . . ?
C2 C3 C7 C8 138.95(18) . . . . ?
C2 C3 C10 C9 -141.98(18) . . . . ?
C2 C3 C10 C11 -20.6(2) . . . . ?
C3 C7 C8 C9 -10.7(3) . . . . ?
C3 C10 C11 C12 101.8(2) . . . . ?
C3 C10 C11 C16 -77.5(2) . . . . ?
C4 N2 C1 O1 -172.3(2) . . . . ?
C4 N2 C1 N1 11.6(3) . . . . ?
C4 C3 C7 C8 -92.7(2) . . . . ?
C4 C3 C10 C9 95.29(18) . . . . ?
C4 C3 C10 C11 -143.32(18) . . . . ?
C5 N1 C1 O1 -7.8(3) . . . . ?
C5 N1 C1 N2 168.3(2) . . . . ?
C5 N1 C2 O2 -5.5(3) . . . . ?
C5 N1 C2 C3 171.2(2) . . . . ?
C6 N2 C1 O1 6.3(3) . . . . ?
C6 N2 C1 N1 -169.8(2) . . . . ?
C6 N2 C4 O3 2.9(3) . . . . ?
C6 N2 C4 C3 -173.25(19) . . . . ?
C7 C3 C4 O3 31.2(3) . . . . ?
C7 C3 C4 N2 -152.70(18) . . . . ?
C7 C3 C10 C9 -20.5(2) . . . . ?
C7 C3 C10 C11 100.9(2) . . . . ?
C7 C8 C9 C10 -3.5(3) . . . . ?
C7 C8 C9 C17 171.3(2) . . . . ?
C8 C9 C10 C3 15.3(2) . . . . ?
C8 C9 C10 C11 -108.2(2) . . . . ?
C8 C9 C17 O4 -148.9(2) . . . . ?
C8 C9 C17 C18 29.5(3) . . . . ?
C9 C10 C11 C12 -143.13(19) . . . . ?
C9 C10 C11 C16 37.6(3) . . . . ?
C9 C17 C18 C19 -142.6(2) . . . . ?
C9 C17 C18 C23 41.2(3) . . . . ?
C10 C3 C4 O3 -80.7(2) . . . . ?
C10 C3 C4 N2 95.4(2) . . . . ?
C10 C3 C7 C8 19.1(2) . . . . ?
C10 C9 C17 O4 25.5(3) . . . . ?
C10 C9 C17 C18 -156.04(19) . . . . ?
C10 C11 C12 C13 -179.1(2) . . . . ?
C10 C11 C16 C15 179.4(2) . . . . ?
C11 C12 C13 C14 -1.1(4) . . . . ?
C12 C11 C16 C15 0.1(3) . . . . ?
C12 C13 C14 C15 1.7(4) . . . . ?
C13 C14 C15 C16 -1.4(4) . . . . ?
C14 C15 C16 C11 0.5(4) . . . . ?
C16 C11 C12 C13 0.2(3) . . . . ?
C17 C9 C10 C3 -159.85(18) . . . . ?
C17 C9 C10 C11 76.7(2) . . . . ?
C17 C18 C19 C20 -175.9(2) . . . . ?
C17 C18 C23 C22 174.0(2) . . . . ?
C18 C19 C20 C21 1.4(4) . . . . ?
C19 C18 C23 C22 -2.2(3) . . . . ?
C19 C20 C21 C22 -1.4(4) . . . . ?
C20 C21 C22 C23 -0.4(4) . . . . ?
C21 C22 C23 C18 2.2(4) . . . . ?
C23 C18 C19 C20 0.4(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_sa4738
_database_code_depnum_ccdc_archive 'CCDC 1525356'
_audit_update_record             
;
2017-01-03 deposited with the CCDC.
2017-05-30 downloaded from the CCDC.
;
_audit_creation_date             2016-05-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H20 N2 O4'
_chemical_formula_sum            'C23 H20 N2 O4'
_chemical_formula_weight         388.41
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   15.040(3)
_cell_length_b                   8.7022(15)
_cell_length_c                   15.900(3)
_cell_angle_alpha                90
_cell_angle_beta                 115.384(2)
_cell_angle_gamma                90
_cell_volume                     1880.1(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5140
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4848
_cell_measurement_theta_min      2.3404
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8478
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.616
_exptl_crystal_size_mid          0.609
_exptl_crystal_size_min          0.347
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12139
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_min         2.998
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 45.0657
	          2theta: -19.8842
scan:
	Number of images: 270
	           Slice: -76.2500 - 58.7500
	     Image width: 0.5000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 45.0657
	          2theta: -19.8842
;
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             4538
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0512
_diffrn_orient_matrix_UB_12      -0.0527
_diffrn_orient_matrix_UB_13      0.0037
_diffrn_orient_matrix_UB_21      0.0184
_diffrn_orient_matrix_UB_22      -0.0100
_diffrn_orient_matrix_UB_23      0.1130
_diffrn_orient_matrix_UB_31      -0.0648
_diffrn_orient_matrix_UB_32      0.0222
_diffrn_orient_matrix_UB_33      0.0125
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4049
_reflns_number_total             4237
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution    
;
'SHELXT (Sheldrick, 2014)'
;
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0488
_refine_ls_restrained_S_all      1.127
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0435P)²+0.7070P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1132
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C19(H19), C20(H20),
 C21(H21), C22(H22), C23(H23)
2.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.31318(7) 0.41143(14) 0.25916(8) 0.0392(3) Uani 1 1 d . . . . .
O2 O 0.63030(7) 0.23807(11) 0.39057(8) 0.0347(2) Uani 1 1 d . . . . .
O3 O 0.54685(7) 0.73769(11) 0.45002(7) 0.0297(2) Uani 1 1 d . . . . .
O4 O 0.86886(8) 0.62009(13) 0.65230(7) 0.0389(3) Uani 1 1 d . . . . .
N1 N 0.47070(8) 0.32107(14) 0.32730(8) 0.0285(3) Uani 1 1 d . . . . .
N2 N 0.43127(8) 0.56784(14) 0.36152(8) 0.0277(3) Uani 1 1 d . . . . .
C1 C 0.39938(10) 0.43211(17) 0.31191(9) 0.0289(3) Uani 1 1 d . . . . .
C2 C 0.57214(10) 0.34225(15) 0.38160(9) 0.0261(3) Uani 1 1 d . . . . .
C3 C 0.60089(9) 0.49188(15) 0.42335(9) 0.0245(3) Uani 1 1 d . . . . .
C4 C 0.53001(9) 0.59506(15) 0.41250(9) 0.0244(3) Uani 1 1 d . . . . .
C5 C 0.43754(12) 0.17738(18) 0.27426(11) 0.0381(3) Uani 1 1 d . . . . .
H5A H 0.3751 0.1480 0.2721 0.057 Uiso 1 1 calc GR . . . .
H5B H 0.4849 0.0978 0.3040 0.057 Uiso 1 1 calc GR . . . .
H5C H 0.4310 0.1926 0.2121 0.057 Uiso 1 1 calc GR . . . .
C6 C 0.35726(10) 0.68600(19) 0.35076(11) 0.0370(3) Uani 1 1 d . . . . .
H6A H 0.3590 0.7644 0.3090 0.055 Uiso 1 1 calc GR . . . .
H6B H 0.3714 0.7308 0.4103 0.055 Uiso 1 1 calc GR . . . .
H6C H 0.2931 0.6399 0.3259 0.055 Uiso 1 1 calc GR . . . .
C7 C 0.70835(9) 0.53092(15) 0.47534(9) 0.0243(3) Uani 1 1 d . . . . .
H7 H 0.7405 0.4501 0.5214 0.029 Uiso 1 1 calc R . . . .
C8 C 0.71912(9) 0.68193(15) 0.52618(9) 0.0252(3) Uani 1 1 d . . . . .
C9 C 0.64427(10) 0.77626(16) 0.51147(9) 0.0271(3) Uani 1 1 d . . . . .
C10 C 0.76044(9) 0.54367(15) 0.41149(9) 0.0252(3) Uani 1 1 d . . . . .
C11 C 0.72384(11) 0.63868(18) 0.33360(10) 0.0334(3) Uani 1 1 d . . . . .
H11 H 0.6667 0.6949 0.3199 0.040 Uiso 1 1 calc R . . . .
C12 C 0.77164(12) 0.6505(2) 0.27605(11) 0.0426(4) Uani 1 1 d . . . . .
H12 H 0.7467 0.7147 0.2243 0.051 Uiso 1 1 calc R . . . .
C13 C 0.85627(13) 0.5666(2) 0.29572(13) 0.0468(4) Uani 1 1 d . . . . .
H13 H 0.8868 0.5712 0.2558 0.056 Uiso 1 1 calc R . . . .
C14 C 0.89544(12) 0.4762(2) 0.37454(13) 0.0453(4) Uani 1 1 d . . . . .
H14 H 0.9535 0.4221 0.3888 0.054 Uiso 1 1 calc R . . . .
C15 C 0.84803(10) 0.46593(17) 0.43279(11) 0.0339(3) Uani 1 1 d . . . . .
H15 H 0.8753 0.4064 0.4865 0.041 Uiso 1 1 calc R . . . .
C16 C 0.64298(11) 0.93138(17) 0.55061(11) 0.0350(3) Uani 1 1 d . . . . .
H16A H 0.6338 1.0082 0.5043 0.052 Uiso 1 1 calc GR . . . .
H16B H 0.7043 0.9490 0.6039 0.052 Uiso 1 1 calc GR . . . .
H16C H 0.5900 0.9369 0.5689 0.052 Uiso 1 1 calc GR . . . .
C17 C 0.82358(10) 0.71659(16) 0.59411(9) 0.0270(3) Uani 1 1 d . . . . .
C18 C 0.87211(10) 0.86088(16) 0.58535(9) 0.0268(3) Uani 1 1 d . . . . .
C19 C 0.83204(11) 0.95296(17) 0.50620(10) 0.0332(3) Uani 1 1 d . . . . .
H19 H 0.7719 0.9269 0.4578 0.040 Uiso 1 1 calc R . . . .
C20 C 0.88126(12) 1.08297(18) 0.49931(11) 0.0396(4) Uani 1 1 d . . . . .
H20 H 0.8541 1.1442 0.4463 0.048 Uiso 1 1 calc R . . . .
C21 C 0.97078(12) 1.12228(18) 0.57103(12) 0.0387(3) Uani 1 1 d . . . . .
H21 H 1.0035 1.2102 0.5664 0.046 Uiso 1 1 calc R . . . .
C22 C 1.01188(11) 1.03071(18) 0.64992(11) 0.0348(3) Uani 1 1 d . . . . .
H22 H 1.0721 1.0571 0.6980 0.042 Uiso 1 1 calc R . . . .
C23 C 0.96318(10) 0.90047(17) 0.65689(9) 0.0300(3) Uani 1 1 d . . . . .
H23 H 0.9911 0.8386 0.7095 0.036 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2184(17) . ?
O2 C2 1.2248(17) . ?
O3 C4 1.3532(16) . ?
O3 C9 1.4095(16) . ?
O4 C17 1.2185(17) . ?
N1 C1 1.3853(18) . ?
N1 C2 1.4063(17) . ?
N1 C5 1.4707(18) . ?
N2 C1 1.3866(18) . ?
N2 C4 1.3735(17) . ?
N2 C6 1.4705(18) . ?
C2 C3 1.4412(19) . ?
C3 C4 1.3472(18) . ?
C3 C7 1.5051(18) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7 0.9800 . ?
C7 C8 1.5147(18) . ?
C7 C10 1.5292(18) . ?
C8 C9 1.3304(19) . ?
C8 C17 1.5070(18) . ?
C9 C16 1.4900(19) . ?
C10 C11 1.391(2) . ?
C10 C15 1.3876(19) . ?
C11 H11 0.9300 . ?
C11 C12 1.389(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.382(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.380(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.393(2) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.4887(19) . ?
C18 C19 1.392(2) . ?
C18 C23 1.3974(19) . ?
C19 H19 0.9300 . ?
C19 C20 1.382(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.383(2) . ?
C21 H21 0.9300 . ?
C21 C22 1.388(2) . ?
C22 H22 0.9300 . ?
C22 C23 1.379(2) . ?
C23 H23 0.9300 . ?

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
C4 O3 C9 117.81(10) . . ?
C1 N1 C2 124.83(12) . . ?
C1 N1 C5 116.44(12) . . ?
C2 N1 C5 118.38(12) . . ?
C1 N2 C6 118.00(11) . . ?
C4 N2 C1 120.36(11) . . ?
C4 N2 C6 121.40(12) . . ?
O1 C1 N1 122.24(14) . . ?
O1 C1 N2 121.59(13) . . ?
N1 C1 N2 116.16(12) . . ?
O2 C2 N1 120.47(12) . . ?
O2 C2 C3 123.84(12) . . ?
N1 C2 C3 115.69(12) . . ?
C2 C3 C7 119.76(11) . . ?
C4 C3 C2 118.59(12) . . ?
C4 C3 C7 121.63(12) . . ?
O3 C4 N2 111.67(11) . . ?
C3 C4 O3 124.51(12) . . ?
C3 C4 N2 123.82(12) . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C3 C7 H7 108.6 . . ?
C3 C7 C8 109.44(10) . . ?
C3 C7 C10 112.76(11) . . ?
C8 C7 H7 108.6 . . ?
C8 C7 C10 108.86(10) . . ?
C10 C7 H7 108.6 . . ?
C9 C8 C7 123.55(12) . . ?
C9 C8 C17 123.10(12) . . ?
C17 C8 C7 113.34(11) . . ?
O3 C9 C16 108.02(11) . . ?
C8 C9 O3 121.65(12) . . ?
C8 C9 C16 130.32(13) . . ?
C11 C10 C7 120.95(12) . . ?
C15 C10 C7 120.37(12) . . ?
C15 C10 C11 118.61(13) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.76(14) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 119.91(16) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.01(15) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 119.96(15) . . ?
C15 C14 H14 120.0 . . ?
C10 C15 C14 120.64(15) . . ?
C10 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C9 C16 H16A 109.5 . . ?
C9 C16 H16B 109.5 . . ?
C9 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4 C17 C8 118.55(13) . . ?
O4 C17 C18 121.02(12) . . ?
C18 C17 C8 120.28(11) . . ?
C19 C18 C17 122.03(12) . . ?
C19 C18 C23 119.17(13) . . ?
C23 C18 C17 118.72(12) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.24(13) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.15(14) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 H21 119.9 . . ?
C20 C21 C22 120.14(14) . . ?
C22 C21 H21 119.9 . . ?
C21 C22 H22 120.1 . . ?
C23 C22 C21 119.89(13) . . ?
C23 C22 H22 120.1 . . ?
C18 C23 H23 119.8 . . ?
C22 C23 C18 120.40(13) . . ?
C22 C23 H23 119.8 . . ?

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
O2 C2 C3 C4 -176.73(13) . . . . ?
O2 C2 C3 C7 5.0(2) . . . . ?
O4 C17 C18 C19 162.80(14) . . . . ?
O4 C17 C18 C23 -13.8(2) . . . . ?
N1 C2 C3 C4 3.96(18) . . . . ?
N1 C2 C3 C7 -174.35(11) . . . . ?
C1 N1 C2 O2 -179.10(13) . . . . ?
C1 N1 C2 C3 0.23(19) . . . . ?
C1 N2 C4 O3 175.29(11) . . . . ?
C1 N2 C4 C3 -4.6(2) . . . . ?
C2 N1 C1 O1 174.89(13) . . . . ?
C2 N1 C1 N2 -6.35(19) . . . . ?
C2 C3 C4 O3 178.20(11) . . . . ?
C2 C3 C4 N2 -1.9(2) . . . . ?
C2 C3 C7 C8 -170.24(11) . . . . ?
C2 C3 C7 C10 68.43(15) . . . . ?
C3 C7 C8 C9 -11.66(18) . . . . ?
C3 C7 C8 C17 169.40(11) . . . . ?
C3 C7 C10 C11 53.03(17) . . . . ?
C3 C7 C10 C15 -130.06(13) . . . . ?
C4 O3 C9 C8 5.96(19) . . . . ?
C4 O3 C9 C16 -174.51(11) . . . . ?
C4 N2 C1 O1 -172.82(13) . . . . ?
C4 N2 C1 N1 8.41(18) . . . . ?
C4 C3 C7 C8 11.51(17) . . . . ?
C4 C3 C7 C10 -109.82(14) . . . . ?
C5 N1 C1 O1 1.8(2) . . . . ?
C5 N1 C1 N2 -179.45(12) . . . . ?
C5 N1 C2 O2 -6.11(19) . . . . ?
C5 N1 C2 C3 173.21(12) . . . . ?
C6 N2 C1 O1 1.7(2) . . . . ?
C6 N2 C1 N1 -177.12(12) . . . . ?
C6 N2 C4 O3 1.01(17) . . . . ?
C6 N2 C4 C3 -178.90(13) . . . . ?
C7 C3 C4 O3 -3.5(2) . . . . ?
C7 C3 C4 N2 176.37(12) . . . . ?
C7 C8 C9 O3 3.6(2) . . . . ?
C7 C8 C9 C16 -175.80(13) . . . . ?
C7 C8 C17 O4 -53.04(16) . . . . ?
C7 C8 C17 C18 122.55(13) . . . . ?
C7 C10 C11 C12 179.69(13) . . . . ?
C7 C10 C15 C14 179.52(13) . . . . ?
C8 C7 C10 C11 -68.63(15) . . . . ?
C8 C7 C10 C15 108.28(14) . . . . ?
C8 C17 C18 C19 -12.68(19) . . . . ?
C8 C17 C18 C23 170.68(12) . . . . ?
C9 O3 C4 N2 174.06(11) . . . . ?
C9 O3 C4 C3 -6.03(19) . . . . ?
C9 C8 C17 O4 128.01(15) . . . . ?
C9 C8 C17 C18 -56.40(18) . . . . ?
C10 C7 C8 C9 112.00(14) . . . . ?
C10 C7 C8 C17 -66.95(13) . . . . ?
C10 C11 C12 C13 0.3(2) . . . . ?
C11 C10 C15 C14 -3.5(2) . . . . ?
C11 C12 C13 C14 -2.7(3) . . . . ?
C12 C13 C14 C15 1.9(3) . . . . ?
C13 C14 C15 C10 1.2(2) . . . . ?
C15 C10 C11 C12 2.7(2) . . . . ?
C17 C8 C9 O3 -177.55(11) . . . . ?
C17 C8 C9 C16 3.0(2) . . . . ?
C17 C18 C19 C20 -177.54(14) . . . . ?
C17 C18 C23 C22 177.93(13) . . . . ?
C18 C19 C20 C21 0.1(2) . . . . ?
C19 C18 C23 C22 1.2(2) . . . . ?
C19 C20 C21 C22 0.4(2) . . . . ?
C20 C21 C22 C23 -0.2(2) . . . . ?
C21 C22 C23 C18 -0.7(2) . . . . ?
C23 C18 C19 C20 -0.9(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
