# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2015

####################################################################### 
# 
# 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_exp_7070
_database_code_depnum_ccdc_archive 'CCDC 1423418'
_audit_update_record             
;
2015-09-24 deposited with the CCDC.
2015-10-30 downloaded from the CCDC.
;
_audit_creation_date             2015-09-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C24 H22 N4 O4'
_chemical_formula_sum            'C24 H22 N4 O4'
_chemical_formula_weight         430.46
_chemical_absolute_configuration syn
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   7.6889(2)
_cell_length_b                   15.5382(5)
_cell_length_c                   16.4272(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1962.58(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1932
_cell_measurement_temperature    99.8(5)
_cell_measurement_theta_max      69.0010
_cell_measurement_theta_min      5.6740
_exptl_absorpt_coefficient_mu    0.832
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68505
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       pillar
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0597
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4748
_diffrn_reflns_theta_full        68.84
_diffrn_reflns_theta_max         68.84
_diffrn_reflns_theta_min         3.92
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.8(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4741
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   32.00  109.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       98.0610  -94.0000 -120.0000 77

#__ type_ start__ end____ width___ exp.time_
  2 omega   45.00   84.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       98.0610  -30.0000   30.0000 39

#__ type_ start__ end____ width___ exp.time_
  3 omega   56.00   91.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       98.0610  -30.0000  120.0000 35

#__ type_ start__ end____ width___ exp.time_
  4 omega   21.00   85.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       98.0610  -30.0000   90.0000 64

#__ type_ start__ end____ width___ exp.time_
  5 omega   21.00   69.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       98.0610  -30.0000 -120.0000 48

#__ type_ start__ end____ width___ exp.time_
  6 omega -103.00   32.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6297    0.0000   90.0000 135
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0997282000
_diffrn_orient_matrix_UB_12      0.0362368000
_diffrn_orient_matrix_UB_13      0.0738339000
_diffrn_orient_matrix_UB_21      -0.0689895000
_diffrn_orient_matrix_UB_22      -0.0743453000
_diffrn_orient_matrix_UB_23      0.0529421000
_diffrn_orient_matrix_UB_31      0.1595100000
_diffrn_orient_matrix_UB_32      -0.0546079000
_diffrn_orient_matrix_UB_33      -0.0233828000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2925
_reflns_number_total             3186
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     63.60
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         3186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0413
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0495P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1021
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C11(H11), C12(H12), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C13(H13), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20),
 C21(H21)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C1A(H1AA,H1AB,H1AC)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O -0.0093(2) 0.60135(10) 0.36947(11) 0.0228(4) Uani 1 d . . .
O2 O 0.0621(2) 0.68723(10) 0.52151(10) 0.0226(4) Uani 1 d . . .
O3 O 0.6732(2) 0.60632(10) 0.45943(12) 0.0260(4) Uani 1 d . . .
H3 H 0.7417 0.5870 0.4258 0.039 Uiso 1 calc . . GR
O4 O 0.2911(2) 0.41237(12) 0.68856(11) 0.0291(4) Uani 1 d . . .
N5 N 0.2009(3) 0.70545(12) 0.36777(12) 0.0192(4) Uani 1 d . . .
N6 N 0.2702(3) 0.58993(12) 0.55736(12) 0.0198(4) Uani 1 d . . .
N7 N 0.4595(3) 0.48505(13) 0.59506(13) 0.0206(4) Uani 1 d . . .
N8 N 0.1894(3) 0.82711(12) 0.28043(13) 0.0231(4) Uani 1 d . . .
C1 C 0.1982(3) 0.64952(14) 0.50763(15) 0.0194(5) Uani 1 d . . .
C2 C 0.0402(3) 0.67172(15) 0.34488(15) 0.0198(5) Uani 1 d . . .
C3 C 0.0214(3) 0.80303(15) 0.25883(15) 0.0209(5) Uani 1 d . . .
C4 C 0.5346(3) 0.42174(15) 0.54361(15) 0.0206(5) Uani 1 d . . .
C5 C 0.2665(3) 0.77934(15) 0.33336(15) 0.0215(5) Uani 1 d . . .
H5 H 0.3769 0.7964 0.3499 0.026 Uiso 1 calc . . R
C6 C 0.3151(3) 0.47351(16) 0.64420(15) 0.0221(5) Uani 1 d . . .
C7 C 0.1858(3) 0.54764(15) 0.62677(15) 0.0202(5) Uani 1 d . . .
H7 H 0.1784 0.5868 0.6734 0.024 Uiso 1 calc . . R
C8 C 0.5251(3) 0.55118(15) 0.46466(16) 0.0205(5) Uani 1 d . . .
C9 C -0.0584(3) 0.72857(16) 0.29013(15) 0.0206(5) Uani 1 d . . .
C10 C 0.5709(3) 0.45645(15) 0.46762(15) 0.0208(5) Uani 1 d . . .
C11 C 0.3060(3) 0.66237(14) 0.43012(14) 0.0191(5) Uani 1 d . . .
H11 H 0.4022 0.7011 0.4439 0.023 Uiso 1 calc . . R
C12 C 0.4527(3) 0.56695(15) 0.55161(15) 0.0193(5) Uani 1 d . . .
H12 H 0.5240 0.6099 0.5798 0.023 Uiso 1 calc . . R
C13 C -0.0721(3) 0.85532(15) 0.20445(16) 0.0236(5) Uani 1 d . . .
H13 H -0.0206 0.9044 0.1828 0.028 Uiso 1 calc . . R
C14 C 0.0056(3) 0.51132(15) 0.60525(15) 0.0210(5) Uani 1 d . . .
H14 H -0.0633 0.5583 0.5818 0.025 Uiso 1 calc . . R
C15 C 0.6392(3) 0.28575(16) 0.50192(17) 0.0252(5) Uani 1 d . . .
H15 H 0.6635 0.2283 0.5129 0.030 Uiso 1 calc . . R
C16 C -0.2298(3) 0.70833(16) 0.26840(15) 0.0241(5) Uani 1 d . . .
H16 H -0.2832 0.6597 0.2900 0.029 Uiso 1 calc . . R
C17 C 0.5658(3) 0.33611(15) 0.56261(16) 0.0227(5) Uani 1 d . . .
H17 H 0.5389 0.3136 0.6135 0.027 Uiso 1 calc . . R
C18 C -0.3186(3) 0.76013(17) 0.21529(16) 0.0254(5) Uani 1 d . . .
H18 H -0.4319 0.7462 0.2005 0.030 Uiso 1 calc . . R
C19 C 0.6774(3) 0.31839(16) 0.42562(16) 0.0247(5) Uani 1 d . . .
H19 H 0.7260 0.2828 0.3862 0.030 Uiso 1 calc . . R
C20 C -0.2398(3) 0.83399(16) 0.18319(15) 0.0244(5) Uani 1 d . . .
H20 H -0.3012 0.8689 0.1473 0.029 Uiso 1 calc . . R
C21 C 0.6431(3) 0.40460(15) 0.40766(16) 0.0222(5) Uani 1 d . . .
H21 H 0.6682 0.4269 0.3564 0.027 Uiso 1 calc . . R
C22 C 0.3865(3) 0.57707(15) 0.40203(16) 0.0203(5) Uani 1 d . . .
H22A H 0.4391 0.5839 0.3487 0.024 Uiso 1 calc . . R
H22B H 0.2976 0.5329 0.3985 0.024 Uiso 1 calc . . R
C23 C -0.0883(3) 0.48011(17) 0.68182(17) 0.0263(6) Uani 1 d . . .
H23A H -0.0281 0.4313 0.7039 0.039 Uiso 1 calc . . GR
H23B H -0.2053 0.4640 0.6682 0.039 Uiso 1 calc . . GR
H23C H -0.0905 0.5255 0.7215 0.039 Uiso 1 calc . . GR
C1A C 0.0182(4) 0.43998(17) 0.54131(17) 0.0287(6) Uani 1 d . . .
H1AA H 0.0711 0.4624 0.4928 0.043 Uiso 1 calc . . GR
H1AB H -0.0962 0.4191 0.5288 0.043 Uiso 1 calc . . GR
H1AC H 0.0878 0.3937 0.5622 0.043 Uiso 1 calc . . GR


_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 C2 1.226(3) . ?
O2 C1 1.221(3) . ?
O3 H3 0.8200 . ?
O3 C8 1.428(3) . ?
O4 C6 1.212(3) . ?
N5 C2 1.394(3) . ?
N5 C5 1.375(3) . ?
N5 C11 1.466(3) . ?
N6 C1 1.353(3) . ?
N6 C7 1.467(3) . ?
N6 C12 1.451(3) . ?
N7 C4 1.420(3) . ?
N7 C6 1.384(3) . ?
N7 C12 1.460(3) . ?
N8 C3 1.391(3) . ?
N8 C5 1.287(3) . ?
C1 C11 1.532(3) . ?
C2 C9 1.471(3) . ?
C3 C9 1.407(3) . ?
C3 C13 1.405(4) . ?
C4 C10 1.388(4) . ?
C4 C17 1.387(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.548(3) . ?
C7 H7 0.9800 . ?
C7 C14 1.538(3) . ?
C8 C10 1.514(3) . ?
C8 C12 1.552(3) . ?
C8 C22 1.535(3) . ?
C9 C16 1.401(4) . ?
C10 C21 1.388(4) . ?
C11 H11 0.9800 . ?
C11 C22 1.534(3) . ?
C12 H12 0.9800 . ?
C13 H13 0.9300 . ?
C13 C20 1.377(4) . ?
C14 H14 0.9800 . ?
C14 C23 1.529(4) . ?
C14 C1A 1.530(3) . ?
C15 H15 0.9300 . ?
C15 C17 1.387(4) . ?
C15 C19 1.384(4) . ?
C16 H16 0.9300 . ?
C16 C18 1.370(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C18 C20 1.401(4) . ?
C19 H19 0.9300 . ?
C19 C21 1.397(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C1A H1AA 0.9600 . ?
C1A H1AB 0.9600 . ?
C1A H1AC 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
C8 O3 H3 109.5 . . ?
C2 N5 C11 120.35(19) . . ?
C5 N5 C2 121.9(2) . . ?
C5 N5 C11 117.80(19) . . ?
C1 N6 C7 126.5(2) . . ?
C1 N6 C12 121.6(2) . . ?
C12 N6 C7 111.59(19) . . ?
C4 N7 C12 109.12(19) . . ?
C6 N7 C4 125.7(2) . . ?
C6 N7 C12 111.67(19) . . ?
C5 N8 C3 116.4(2) . . ?
O2 C1 N6 124.5(2) . . ?
O2 C1 C11 123.8(2) . . ?
N6 C1 C11 111.70(19) . . ?
O1 C2 N5 121.4(2) . . ?
O1 C2 C9 125.2(2) . . ?
N5 C2 C9 113.3(2) . . ?
N8 C3 C9 122.2(2) . . ?
N8 C3 C13 118.8(2) . . ?
C13 C3 C9 119.0(2) . . ?
C10 C4 N7 110.4(2) . . ?
C17 C4 N7 126.9(2) . . ?
C17 C4 C10 122.7(2) . . ?
N5 C5 H5 116.9 . . ?
N8 C5 N5 126.2(2) . . ?
N8 C5 H5 116.9 . . ?
O4 C6 N7 125.1(2) . . ?
O4 C6 C7 126.6(2) . . ?
N7 C6 C7 108.10(19) . . ?
N6 C7 C6 101.13(18) . . ?
N6 C7 H7 110.8 . . ?
N6 C7 C14 112.60(19) . . ?
C6 C7 H7 110.8 . . ?
C14 C7 C6 110.37(19) . . ?
C14 C7 H7 110.8 . . ?
O3 C8 C10 113.55(19) . . ?
O3 C8 C12 104.27(19) . . ?
O3 C8 C22 110.86(19) . . ?
C10 C8 C12 101.97(19) . . ?
C10 C8 C22 116.0(2) . . ?
C22 C8 C12 109.07(19) . . ?
C3 C9 C2 119.5(2) . . ?
C16 C9 C2 120.4(2) . . ?
C16 C9 C3 120.1(2) . . ?
C4 C10 C8 111.1(2) . . ?
C4 C10 C21 119.5(2) . . ?
C21 C10 C8 129.4(2) . . ?
N5 C11 C1 109.99(18) . . ?
N5 C11 H11 107.2 . . ?
N5 C11 C22 114.00(19) . . ?
C1 C11 H11 107.2 . . ?
C1 C11 C22 110.83(18) . . ?
C22 C11 H11 107.2 . . ?
N6 C12 N7 102.55(18) . . ?
N6 C12 C8 116.4(2) . . ?
N6 C12 H12 110.0 . . ?
N7 C12 C8 107.42(18) . . ?
N7 C12 H12 110.0 . . ?
C8 C12 H12 110.0 . . ?
C3 C13 H13 120.0 . . ?
C20 C13 C3 120.1(2) . . ?
C20 C13 H13 120.0 . . ?
C7 C14 H14 107.7 . . ?
C23 C14 C7 110.7(2) . . ?
C23 C14 H14 107.7 . . ?
C23 C14 C1A 111.4(2) . . ?
C1A C14 C7 111.5(2) . . ?
C1A C14 H14 107.7 . . ?
C17 C15 H15 119.0 . . ?
C19 C15 H15 119.0 . . ?
C19 C15 C17 122.0(2) . . ?
C9 C16 H16 120.0 . . ?
C18 C16 C9 120.0(2) . . ?
C18 C16 H16 120.0 . . ?
C4 C17 H17 121.6 . . ?
C15 C17 C4 116.7(2) . . ?
C15 C17 H17 121.6 . . ?
C16 C18 H18 119.8 . . ?
C16 C18 C20 120.4(2) . . ?
C20 C18 H18 119.8 . . ?
C15 C19 H19 119.9 . . ?
C15 C19 C21 120.2(2) . . ?
C21 C19 H19 119.9 . . ?
C13 C20 C18 120.5(2) . . ?
C13 C20 H20 119.8 . . ?
C18 C20 H20 119.8 . . ?
C10 C21 C19 118.8(2) . . ?
C10 C21 H21 120.6 . . ?
C19 C21 H21 120.6 . . ?
C8 C22 H22A 110.2 . . ?
C8 C22 H22B 110.2 . . ?
C11 C22 C8 107.75(19) . . ?
C11 C22 H22A 110.2 . . ?
C11 C22 H22B 110.2 . . ?
H22A C22 H22B 108.5 . . ?
C14 C23 H23A 109.5 . . ?
C14 C23 H23B 109.5 . . ?
C14 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C14 C1A H1AA 109.5 . . ?
C14 C1A H1AB 109.5 . . ?
C14 C1A H1AC 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 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
O1 C2 C9 C3 -172.6(2) . . . . ?
O1 C2 C9 C16 6.6(4) . . . . ?
O2 C1 C11 N5 -15.9(3) . . . . ?
O2 C1 C11 C22 -142.8(2) . . . . ?
O3 C8 C10 C4 110.8(2) . . . . ?
O3 C8 C10 C21 -67.9(3) . . . . ?
O3 C8 C12 N6 126.6(2) . . . . ?
O3 C8 C12 N7 -119.13(18) . . . . ?
O3 C8 C22 C11 -71.2(2) . . . . ?
O4 C6 C7 N6 -168.3(2) . . . . ?
O4 C6 C7 C14 -48.9(3) . . . . ?
N5 C2 C9 C3 7.6(3) . . . . ?
N5 C2 C9 C16 -173.3(2) . . . . ?
N5 C11 C22 C8 166.63(19) . . . . ?
N6 C1 C11 N5 162.57(18) . . . . ?
N6 C1 C11 C22 35.6(3) . . . . ?
N6 C7 C14 C23 -171.5(2) . . . . ?
N6 C7 C14 C1A 63.9(3) . . . . ?
N7 C4 C10 C8 2.0(3) . . . . ?
N7 C4 C10 C21 -179.1(2) . . . . ?
N7 C4 C17 C15 179.3(2) . . . . ?
N7 C6 C7 N6 7.0(2) . . . . ?
N7 C6 C7 C14 126.4(2) . . . . ?
N8 C3 C9 C2 -2.7(4) . . . . ?
N8 C3 C9 C16 178.1(2) . . . . ?
N8 C3 C13 C20 -178.8(2) . . . . ?
C1 N6 C7 C6 167.0(2) . . . . ?
C1 N6 C7 C14 49.2(3) . . . . ?
C1 N6 C12 N7 -162.4(2) . . . . ?
C1 N6 C12 C8 -45.5(3) . . . . ?
C1 C11 C22 C8 -68.6(2) . . . . ?
C2 N5 C5 N8 2.9(4) . . . . ?
C2 N5 C11 C1 -54.0(3) . . . . ?
C2 N5 C11 C22 71.2(3) . . . . ?
C2 C9 C16 C18 -177.9(2) . . . . ?
C3 N8 C5 N5 2.7(3) . . . . ?
C3 C9 C16 C18 1.3(4) . . . . ?
C3 C13 C20 C18 -0.1(4) . . . . ?
C4 N7 C6 O4 46.4(4) . . . . ?
C4 N7 C6 C7 -129.0(2) . . . . ?
C4 N7 C12 N6 125.19(19) . . . . ?
C4 N7 C12 C8 2.0(2) . . . . ?
C4 C10 C21 C19 0.0(4) . . . . ?
C5 N5 C2 O1 172.3(2) . . . . ?
C5 N5 C2 C9 -7.8(3) . . . . ?
C5 N5 C11 C1 126.0(2) . . . . ?
C5 N5 C11 C22 -108.8(2) . . . . ?
C5 N8 C3 C9 -2.7(3) . . . . ?
C5 N8 C3 C13 176.8(2) . . . . ?
C6 N7 C4 C10 134.4(2) . . . . ?
C6 N7 C4 C17 -43.9(4) . . . . ?
C6 N7 C12 N6 -18.2(3) . . . . ?
C6 N7 C12 C8 -141.4(2) . . . . ?
C6 C7 C14 C23 76.3(2) . . . . ?
C6 C7 C14 C1A -48.3(3) . . . . ?
C7 N6 C1 O2 12.8(4) . . . . ?
C7 N6 C1 C11 -165.6(2) . . . . ?
C7 N6 C12 N7 23.2(2) . . . . ?
C7 N6 C12 C8 140.1(2) . . . . ?
C8 C10 C21 C19 178.6(2) . . . . ?
C9 C3 C13 C20 0.7(4) . . . . ?
C9 C16 C18 C20 -0.7(4) . . . . ?
C10 C4 C17 C15 1.1(4) . . . . ?
C10 C8 C12 N6 -115.0(2) . . . . ?
C10 C8 C12 N7 -0.7(2) . . . . ?
C10 C8 C22 C11 157.4(2) . . . . ?
C11 N5 C2 O1 -7.7(3) . . . . ?
C11 N5 C2 C9 172.21(19) . . . . ?
C11 N5 C5 N8 -177.1(2) . . . . ?
C12 N6 C1 O2 -160.7(2) . . . . ?
C12 N6 C1 C11 20.9(3) . . . . ?
C12 N6 C7 C6 -18.9(2) . . . . ?
C12 N6 C7 C14 -136.7(2) . . . . ?
C12 N7 C4 C10 -2.5(3) . . . . ?
C12 N7 C4 C17 179.1(2) . . . . ?
C12 N7 C6 O4 -177.6(2) . . . . ?
C12 N7 C6 C7 7.1(3) . . . . ?
C12 C8 C10 C4 -0.7(2) . . . . ?
C12 C8 C10 C21 -179.4(2) . . . . ?
C12 C8 C22 C11 43.1(2) . . . . ?
C13 C3 C9 C2 177.9(2) . . . . ?
C13 C3 C9 C16 -1.3(4) . . . . ?
C15 C19 C21 C10 0.2(4) . . . . ?
C16 C18 C20 C13 0.1(4) . . . . ?
C17 C4 C10 C8 -179.5(2) . . . . ?
C17 C4 C10 C21 -0.7(4) . . . . ?
C17 C15 C19 C21 0.3(4) . . . . ?
C19 C15 C17 C4 -1.0(4) . . . . ?
C22 C8 C10 C4 -119.1(2) . . . . ?
C22 C8 C10 C21 62.2(3) . . . . ?
C22 C8 C12 N6 8.2(3) . . . . ?
C22 C8 C12 N7 122.4(2) . . . . ?

_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_exp_10604
_database_code_depnum_ccdc_archive 'CCDC 1423426'
_audit_update_record             
;
2015-09-24 deposited with the CCDC.
2015-10-30 downloaded from the CCDC.
;
_audit_creation_date             2015-09-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C24 H22 N4 O4, 2(H2 O)'
_chemical_formula_sum            'C24 H26 N4 O6'
_chemical_formula_weight         466.49
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 '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'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   9.3200(6)
_cell_length_b                   10.5489(6)
_cell_length_c                   12.1772(7)
_cell_angle_alpha                95.818(5)
_cell_angle_beta                 90.490(5)
_cell_angle_gamma                111.805(6)
_cell_volume                     1104.43(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1875
_cell_measurement_temperature    173.00(14)
_cell_measurement_theta_max      60.2190
_cell_measurement_theta_min      4.5470
_exptl_absorpt_coefficient_mu    0.849
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       pillar
_exptl_crystal_F_000             492
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_unetI/netI     0.0662
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5671
_diffrn_reflns_theta_full        60.18
_diffrn_reflns_theta_max         60.18
_diffrn_reflns_theta_min         3.65
_diffrn_ambient_temperature      173.00(14)
_diffrn_detector_area_resol_mean 16.1903
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   13.00  101.20   0.7000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       32.3584   57.0000  -90.0000 126

#__ type_ start__ end____ width___ exp.time_
  2 omega  -33.00   55.20   0.7000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       32.3584  -57.0000    0.0000 126

#__ type_ start__ end____ width___ exp.time_
  3 omega   10.00  102.40   0.7000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       32.3584   57.0000  150.0000 132

#__ type_ start__ end____ width___ exp.time_
  4 omega   77.00  110.60   0.7000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       32.3584  178.0000    0.0000 48

#__ type_ start__ end____ width___ exp.time_
  5 omega -156.00 -107.00   0.7000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -75.0000  178.0000  -30.0000 70

#__ type_ start__ end____ width___ exp.time_
  6 omega  -82.00  -54.70   0.7000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -75.0000  178.0000  -30.0000 39

#__ type_ start__ end____ width___ exp.time_
  7 omega -130.00 -102.00   0.7000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -75.0000 -112.0000   90.0000 40

#__ type_ start__ end____ width___ exp.time_
  8 omega -148.00 -114.40   0.7000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -75.0000  -92.0000 -150.0000 48

#__ type_ start__ end____ width___ exp.time_
  9 omega   24.00   82.10   0.7000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -50.0000  150.0000 83

#__ type_ start__ end____ width___ exp.time_
 10 omega   29.00  103.20   0.7000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -92.0000  150.0000 106

#__ type_ start__ end____ width___ exp.time_
 11 omega   38.00   99.60   0.7000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -92.0000  -90.0000 88

#__ type_ start__ end____ width___ exp.time_
 12 omega   32.00   65.60   0.7000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -25.0000  -90.0000 48

#__ type_ start__ end____ width___ exp.time_
 13 omega   26.00   59.60   0.7000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -38.0000    0.0000 48

#__ type_ start__ end____ width___ exp.time_
 14 omega   21.00   70.00   0.7000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -38.0000 -150.0000 70

#__ type_ start__ end____ width___ exp.time_
 15 omega   34.00   69.70   0.7000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -50.0000  -30.0000 51

#__ type_ start__ end____ width___ exp.time_
 16 omega   16.00   57.30   0.7000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -25.0000   90.0000 59

#__ type_ start__ end____ width___ exp.time_
 17 omega   19.00   50.50   0.7000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -25.0000   60.0000 45

#__ type_ start__ end____ width___ exp.time_
 18 omega   23.00   70.60   0.7000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -112.0000  120.0000 68

#__ type_ start__ end____ width___ exp.time_
 19 omega   17.00   68.10   0.7000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -38.0000  -30.0000 73

#__ type_ start__ end____ width___ exp.time_
 20 omega   28.00   63.70   0.7000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -25.0000 -120.0000 51

#__ type_ start__ end____ width___ exp.time_
 21 omega   32.00  114.60   0.7000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -92.0000  -30.0000 118

#__ type_ start__ end____ width___ exp.time_
 22 omega   76.00  101.20   0.7000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -92.0000   60.0000 36

#__ type_ start__ end____ width___ exp.time_
 23 omega   18.00  150.30   0.7000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   12.0000  -90.0000 189
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0563498000
_diffrn_orient_matrix_UB_12      -0.1121693000
_diffrn_orient_matrix_UB_13      0.0787808000
_diffrn_orient_matrix_UB_21      -0.1416113000
_diffrn_orient_matrix_UB_22      -0.0805012000
_diffrn_orient_matrix_UB_23      -0.0792300000
_diffrn_orient_matrix_UB_31      0.0924495000
_diffrn_orient_matrix_UB_32      -0.0774408000
_diffrn_orient_matrix_UB_33      -0.0610603000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2549
_reflns_number_total             3246
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     58.86
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         3246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0380
_refine_ls_restrained_S_all      0.960
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0339P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0932
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O5(H5A,H5B), O6(H6A,H6B)
2.b Ternary CH refined with riding coordinates:
 C3(H3), C6(H6), C10(H10), C17(H17)
2.c Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.d Aromatic/amide H refined with riding coordinates:
 C8(H8), C13(H13), C14(H14), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21),
 C22(H22)
2.e Idealised Me refined as rotating group:
 C1A(H1AA,H1AB,H1AC), C1B(H1BA,H1BB,H1BC)
2.f Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 1.05347(14) 0.16161(13) 0.20757(12) 0.0238(3) Uani 1 d . . .
H1 H 1.0730 0.1288 0.2613 0.036 Uiso 1 calc . . GR
O2 O 0.66266(16) 0.36165(13) 0.14002(11) 0.0254(3) Uani 1 d . . .
O3 O 0.90866(15) 0.51709(13) 0.39517(12) 0.0268(3) Uani 1 d . . .
O4 O 0.55086(16) -0.04180(14) -0.12274(12) 0.0279(3) Uani 1 d . . .
O5 O 1.15597(16) 0.08533(14) 0.39890(13) 0.0301(4) Uani 1 d . . .
H5A H 1.2524 0.1307 0.4113 0.045 Uiso 1 d . . G
H5B H 1.1350 0.0023 0.4104 0.045 Uiso 1 d . . G
O6 O 0.96920(19) 0.18199(15) 0.53874(14) 0.0411(4) Uani 1 d . . .
H6A H 1.0344 0.1655 0.4972 0.062 Uiso 1 d . . G
H6B H 0.9998 0.2679 0.5583 0.062 Uiso 1 d . . G
N7 N 0.79134(18) 0.23590(15) 0.05720(13) 0.0188(4) Uani 1 d . . .
N8 N 0.71564(18) 0.30830(15) 0.34812(13) 0.0194(4) Uani 1 d . . .
N9 N 0.76787(18) 0.01839(15) -0.00712(13) 0.0201(4) Uani 1 d . . .
N10 N 0.47807(18) 0.23773(16) 0.43698(14) 0.0227(4) Uani 1 d . . .
C1 C 0.6954(2) 0.44398(18) 0.51242(16) 0.0188(4) Uani 1 d . . .
C2 C 0.8956(2) 0.09236(18) 0.17308(16) 0.0192(4) Uani 1 d . . .
C3 C 0.8723(2) 0.14148(18) 0.06178(16) 0.0182(4) Uani 1 d . . .
H3 H 0.9718 0.1783 0.0272 0.022 Uiso 1 calc . . R
C4 C 0.5448(2) 0.34787(18) 0.51874(16) 0.0197(4) Uani 1 d . . .
C5 C 0.7644(2) -0.10059(19) 0.03874(17) 0.0206(4) Uani 1 d . . .
C6 C 0.7015(2) 0.19918(19) -0.04948(16) 0.0202(4) Uani 1 d . . .
H6 H 0.6072 0.2190 -0.0416 0.024 Uiso 1 calc . . R
C7 C 0.7446(2) 0.29491(18) 0.14733(16) 0.0192(4) Uani 1 d . . .
C9 C 0.8461(2) -0.06176(19) 0.14046(17) 0.0194(4) Uani 1 d . . .
C10 C 0.8020(2) 0.27150(18) 0.25832(16) 0.0198(4) Uani 1 d . . .
H10 H 0.9113 0.3315 0.2709 0.024 Uiso 1 calc . . R
C11 C 0.7842(2) 0.43139(18) 0.41685(16) 0.0195(4) Uani 1 d . . .
C8 C 0.5644(2) 0.22410(19) 0.35881(17) 0.0226(5) Uani 1 d . . .
H8 H 0.5206 0.1505 0.3043 0.027 Uiso 1 calc . . R
C12 C 0.7895(2) 0.12231(18) 0.25751(17) 0.0203(4) Uani 1 d . . .
H12A H 0.8185 0.1074 0.3304 0.024 Uiso 1 calc . . R
H12B H 0.6834 0.0604 0.2390 0.024 Uiso 1 calc . . R
C13 C 0.7574(2) 0.55282(19) 0.59604(17) 0.0218(4) Uani 1 d . . .
H13 H 0.8577 0.6163 0.5924 0.026 Uiso 1 calc . . R
C14 C 0.5203(2) 0.4725(2) 0.68933(17) 0.0242(5) Uani 1 d . . .
H14 H 0.4615 0.4835 0.7482 0.029 Uiso 1 calc . . R
C15 C 0.6600(2) 0.0439(2) -0.06672(16) 0.0216(4) Uani 1 d . . .
C16 C 0.6921(2) -0.23651(19) -0.00458(18) 0.0245(5) Uani 1 d . . .
H16 H 0.6357 -0.2612 -0.0720 0.029 Uiso 1 calc . . R
C17 C 0.7937(2) 0.2724(2) -0.14385(18) 0.0286(5) Uani 1 d . . .
H17 H 0.8908 0.2566 -0.1464 0.034 Uiso 1 calc . . R
C18 C 0.4577(2) 0.36369(19) 0.60864(17) 0.0233(5) Uani 1 d . . .
H18 H 0.3576 0.3006 0.6137 0.028 Uiso 1 calc . . R
C19 C 0.8623(2) -0.16044(19) 0.20009(18) 0.0237(5) Uani 1 d . . .
H19 H 0.9177 -0.1358 0.2679 0.028 Uiso 1 calc . . R
C20 C 0.6702(2) 0.56628(19) 0.68387(17) 0.0237(5) Uani 1 d . . .
H20 H 0.7120 0.6385 0.7398 0.028 Uiso 1 calc . . R
C21 C 0.7942(2) -0.29748(19) 0.15658(18) 0.0269(5) Uani 1 d . . .
H21 H 0.8069 -0.3651 0.1945 0.032 Uiso 1 calc . . R
C22 C 0.7078(2) -0.33439(19) 0.05776(18) 0.0266(5) Uani 1 d . . .
H22 H 0.6589 -0.4270 0.0322 0.032 Uiso 1 calc . . R
C1A C 0.7057(3) 0.2157(2) -0.25458(19) 0.0433(6) Uani 1 d . . .
H1AA H 0.6945 0.1215 -0.2718 0.065 Uiso 1 calc . . GR
H1AB H 0.7617 0.2685 -0.3109 0.065 Uiso 1 calc . . GR
H1AC H 0.6052 0.2211 -0.2511 0.065 Uiso 1 calc . . GR
C1B C 0.8326(3) 0.4260(2) -0.1214(2) 0.0430(6) Uani 1 d . . .
H1BA H 0.7393 0.4443 -0.1255 0.064 Uiso 1 calc . . GR
H1BB H 0.9013 0.4722 -0.1755 0.064 Uiso 1 calc . . GR
H1BC H 0.8819 0.4587 -0.0490 0.064 Uiso 1 calc . . GR


_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 H1 0.8200 . ?
O1 C2 1.416(2) . ?
O2 C7 1.224(2) . ?
O3 C11 1.228(2) . ?
O4 C15 1.223(2) . ?
O5 H5A 0.8501 . ?
O5 H5B 0.8501 . ?
O6 H6A 0.8501 . ?
O6 H6B 0.8500 . ?
N7 C3 1.461(2) . ?
N7 C6 1.475(2) . ?
N7 C7 1.361(2) . ?
N8 C10 1.468(2) . ?
N8 C11 1.396(2) . ?
N8 C8 1.375(3) . ?
N9 C3 1.471(2) . ?
N9 C5 1.414(3) . ?
N9 C15 1.356(3) . ?
N10 C4 1.395(3) . ?
N10 C8 1.282(3) . ?
C1 C4 1.402(3) . ?
C1 C11 1.457(3) . ?
C1 C13 1.396(3) . ?
C2 C3 1.541(3) . ?
C2 C9 1.524(3) . ?
C2 C12 1.522(3) . ?
C3 H3 0.9800 . ?
C4 C18 1.401(3) . ?
C5 C9 1.390(3) . ?
C5 C16 1.382(3) . ?
C6 H6 0.9800 . ?
C6 C15 1.528(3) . ?
C6 C17 1.536(3) . ?
C7 C10 1.526(3) . ?
C9 C19 1.379(3) . ?
C10 H10 0.9800 . ?
C10 C12 1.533(3) . ?
C8 H8 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13 0.9300 . ?
C13 C20 1.376(3) . ?
C14 H14 0.9300 . ?
C14 C18 1.374(3) . ?
C14 C20 1.387(3) . ?
C16 H16 0.9300 . ?
C16 C22 1.391(3) . ?
C17 H17 0.9800 . ?
C17 C1A 1.517(3) . ?
C17 C1B 1.518(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C19 C21 1.390(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C21 C22 1.379(3) . ?
C22 H22 0.9300 . ?
C1A H1AA 0.9600 . ?
C1A H1AB 0.9600 . ?
C1A H1AC 0.9600 . ?
C1B H1BA 0.9600 . ?
C1B H1BB 0.9600 . ?
C1B H1BC 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
C2 O1 H1 109.5 . . ?
H5A O5 H5B 109.5 . . ?
H6A O6 H6B 109.5 . . ?
C3 N7 C6 107.26(13) . . ?
C7 N7 C3 124.38(16) . . ?
C7 N7 C6 121.30(15) . . ?
C11 N8 C10 119.99(15) . . ?
C8 N8 C10 118.97(15) . . ?
C8 N8 C11 120.92(16) . . ?
C5 N9 C3 109.50(15) . . ?
C15 N9 C3 112.53(15) . . ?
C15 N9 C5 131.83(16) . . ?
C8 N10 C4 116.70(17) . . ?
C4 C1 C11 119.54(17) . . ?
C13 C1 C4 119.82(18) . . ?
C13 C1 C11 120.61(18) . . ?
O1 C2 C3 107.02(15) . . ?
O1 C2 C9 115.05(15) . . ?
O1 C2 C12 111.67(15) . . ?
C9 C2 C3 101.17(15) . . ?
C12 C2 C3 110.46(15) . . ?
C12 C2 C9 110.86(15) . . ?
N7 C3 N9 101.95(14) . . ?
N7 C3 C2 119.60(15) . . ?
N7 C3 H3 109.7 . . ?
N9 C3 C2 105.64(14) . . ?
N9 C3 H3 109.7 . . ?
C2 C3 H3 109.7 . . ?
N10 C4 C1 121.76(18) . . ?
N10 C4 C18 118.95(18) . . ?
C18 C4 C1 119.28(17) . . ?
C9 C5 N9 109.13(15) . . ?
C16 C5 N9 128.32(19) . . ?
C16 C5 C9 122.55(18) . . ?
N7 C6 H6 109.8 . . ?
N7 C6 C15 101.17(15) . . ?
N7 C6 C17 113.30(16) . . ?
C15 C6 H6 109.8 . . ?
C15 C6 C17 112.55(16) . . ?
C17 C6 H6 109.8 . . ?
O2 C7 N7 122.61(18) . . ?
O2 C7 C10 122.45(17) . . ?
N7 C7 C10 114.93(16) . . ?
C5 C9 C2 110.77(16) . . ?
C19 C9 C2 129.20(18) . . ?
C19 C9 C5 119.85(17) . . ?
N8 C10 C7 110.37(15) . . ?
N8 C10 H10 108.2 . . ?
N8 C10 C12 110.98(15) . . ?
C7 C10 H10 108.2 . . ?
C7 C10 C12 110.83(15) . . ?
C12 C10 H10 108.2 . . ?
O3 C11 N8 120.54(17) . . ?
O3 C11 C1 125.66(17) . . ?
N8 C11 C1 113.80(16) . . ?
N8 C8 H8 117.0 . . ?
N10 C8 N8 126.00(17) . . ?
N10 C8 H8 117.0 . . ?
C2 C12 C10 109.81(15) . . ?
C2 C12 H12A 109.7 . . ?
C2 C12 H12B 109.7 . . ?
C10 C12 H12A 109.7 . . ?
C10 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
C1 C13 H13 120.0 . . ?
C20 C13 C1 120.02(19) . . ?
C20 C13 H13 120.0 . . ?
C18 C14 H14 119.7 . . ?
C18 C14 C20 120.68(19) . . ?
C20 C14 H14 119.7 . . ?
O4 C15 N9 126.12(18) . . ?
O4 C15 C6 127.29(18) . . ?
N9 C15 C6 106.58(16) . . ?
C5 C16 H16 121.7 . . ?
C5 C16 C22 116.6(2) . . ?
C22 C16 H16 121.7 . . ?
C6 C17 H17 108.2 . . ?
C1A C17 C6 111.31(18) . . ?
C1A C17 H17 108.2 . . ?
C1A C17 C1B 110.83(18) . . ?
C1B C17 C6 110.00(18) . . ?
C1B C17 H17 108.2 . . ?
C4 C18 H18 120.0 . . ?
C14 C18 C4 119.96(19) . . ?
C14 C18 H18 120.0 . . ?
C9 C19 H19 120.7 . . ?
C9 C19 C21 118.5(2) . . ?
C21 C19 H19 120.7 . . ?
C13 C20 C14 120.24(18) . . ?
C13 C20 H20 119.9 . . ?
C14 C20 H20 119.9 . . ?
C19 C21 H21 119.6 . . ?
C22 C21 C19 120.76(19) . . ?
C22 C21 H21 119.6 . . ?
C16 C22 H22 119.2 . . ?
C21 C22 C16 121.64(17) . . ?
C21 C22 H22 119.2 . . ?
C17 C1A H1AA 109.5 . . ?
C17 C1A H1AB 109.5 . . ?
C17 C1A H1AC 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
C17 C1B H1BA 109.5 . . ?
C17 C1B H1BB 109.5 . . ?
C17 C1B H1BC 109.5 . . ?
H1BA C1B H1BB 109.5 . . ?
H1BA C1B H1BC 109.5 . . ?
H1BB C1B H1BC 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
O1 C2 C3 N7 -106.28(17) . . . . ?
O1 C2 C3 N9 139.74(14) . . . . ?
O1 C2 C9 C5 -130.70(17) . . . . ?
O1 C2 C9 C19 54.4(3) . . . . ?
O1 C2 C12 C10 70.4(2) . . . . ?
O2 C7 C10 N8 14.1(2) . . . . ?
O2 C7 C10 C12 137.41(18) . . . . ?
N7 C6 C15 O4 155.92(19) . . . . ?
N7 C6 C15 N9 -23.85(19) . . . . ?
N7 C6 C17 C1A 171.34(16) . . . . ?
N7 C6 C17 C1B -65.4(2) . . . . ?
N7 C7 C10 N8 -165.88(14) . . . . ?
N7 C7 C10 C12 -42.5(2) . . . . ?
N8 C10 C12 C2 -173.11(15) . . . . ?
N9 C5 C9 C2 6.2(2) . . . . ?
N9 C5 C9 C19 -178.33(16) . . . . ?
N9 C5 C16 C22 179.61(18) . . . . ?
N10 C4 C18 C14 -179.07(18) . . . . ?
C1 C4 C18 C14 0.0(3) . . . . ?
C1 C13 C20 C14 -0.5(3) . . . . ?
C2 C9 C19 C21 173.85(18) . . . . ?
C3 N7 C6 C15 32.61(18) . . . . ?
C3 N7 C6 C17 -88.10(18) . . . . ?
C3 N7 C7 O2 -171.90(17) . . . . ?
C3 N7 C7 C10 8.0(2) . . . . ?
C3 N9 C5 C9 7.0(2) . . . . ?
C3 N9 C5 C16 -173.98(18) . . . . ?
C3 N9 C15 O4 -172.93(18) . . . . ?
C3 N9 C15 C6 6.8(2) . . . . ?
C3 C2 C9 C5 -15.76(19) . . . . ?
C3 C2 C9 C19 169.29(19) . . . . ?
C3 C2 C12 C10 -48.6(2) . . . . ?
C4 N10 C8 N8 -0.4(3) . . . . ?
C4 C1 C11 O3 170.75(19) . . . . ?
C4 C1 C11 N8 -9.9(3) . . . . ?
C4 C1 C13 C20 -0.6(3) . . . . ?
C5 N9 C3 N7 -142.61(15) . . . . ?
C5 N9 C3 C2 -16.90(19) . . . . ?
C5 N9 C15 O4 -24.0(3) . . . . ?
C5 N9 C15 C6 155.77(18) . . . . ?
C5 C9 C19 C21 -0.7(3) . . . . ?
C5 C16 C22 C21 -1.4(3) . . . . ?
C6 N7 C3 N9 -28.82(18) . . . . ?
C6 N7 C3 C2 -144.75(16) . . . . ?
C6 N7 C7 O2 -25.1(3) . . . . ?
C6 N7 C7 C10 154.84(16) . . . . ?
C7 N7 C3 N9 121.84(17) . . . . ?
C7 N7 C3 C2 5.9(3) . . . . ?
C7 N7 C6 C15 -119.15(17) . . . . ?
C7 N7 C6 C17 120.14(18) . . . . ?
C7 C10 C12 C2 63.9(2) . . . . ?
C9 C2 C3 N7 132.94(16) . . . . ?
C9 C2 C3 N9 18.96(18) . . . . ?
C9 C2 C12 C10 -159.88(16) . . . . ?
C9 C5 C16 C22 -1.5(3) . . . . ?
C9 C19 C21 C22 -2.2(3) . . . . ?
C10 N8 C11 O3 8.8(3) . . . . ?
C10 N8 C11 C1 -170.65(16) . . . . ?
C10 N8 C8 N10 175.00(19) . . . . ?
C11 N8 C10 C7 -103.85(19) . . . . ?
C11 N8 C10 C12 132.88(17) . . . . ?
C11 N8 C8 N10 -8.9(3) . . . . ?
C11 C1 C4 N10 1.6(3) . . . . ?
C11 C1 C4 C18 -177.42(17) . . . . ?
C11 C1 C13 C20 177.64(18) . . . . ?
C8 N8 C10 C7 72.3(2) . . . . ?
C8 N8 C10 C12 -51.0(2) . . . . ?
C8 N8 C11 O3 -167.24(18) . . . . ?
C8 N8 C11 C1 13.3(3) . . . . ?
C8 N10 C4 C1 3.9(3) . . . . ?
C8 N10 C4 C18 -177.12(18) . . . . ?
C12 C2 C3 N7 15.5(2) . . . . ?
C12 C2 C3 N9 -98.50(17) . . . . ?
C12 C2 C9 C5 101.40(19) . . . . ?
C12 C2 C9 C19 -73.6(2) . . . . ?
C13 C1 C4 N10 179.85(18) . . . . ?
C13 C1 C4 C18 0.8(3) . . . . ?
C13 C1 C11 O3 -7.5(3) . . . . ?
C13 C1 C11 N8 171.91(17) . . . . ?
C15 N9 C3 N7 13.3(2) . . . . ?
C15 N9 C3 C2 139.02(16) . . . . ?
C15 N9 C5 C9 -142.6(2) . . . . ?
C15 N9 C5 C16 36.4(3) . . . . ?
C15 C6 C17 C1A 57.3(2) . . . . ?
C15 C6 C17 C1B -179.44(18) . . . . ?
C16 C5 C9 C2 -172.90(17) . . . . ?
C16 C5 C9 C19 2.6(3) . . . . ?
C17 C6 C15 O4 -82.8(2) . . . . ?
C17 C6 C15 N9 97.39(19) . . . . ?
C18 C14 C20 C13 1.3(3) . . . . ?
C19 C21 C22 C16 3.3(3) . . . . ?
C20 C14 C18 C4 -1.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
