# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1547674'
_audit_update_record             
;
2017-05-03 deposited with the CCDC.
2017-05-05 downloaded from the CCDC.
;
_audit_creation_date             2016-12-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r1)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H23 N O6'
_chemical_formula_sum            'C21 H23 N O6'
_chemical_formula_weight         385.40
_chemical_absolute_configuration unk
_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      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_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.760(3)
_cell_length_b                   13.957(5)
_cell_length_c                   16.322(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1995.7(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2141
_cell_measurement_temperature    293
_cell_measurement_theta_max      67.8
_cell_measurement_theta_min      23.0
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.665
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    "'not measured'"
_exptl_crystal_description       Prism
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1949
_diffrn_reflns_av_unetI/netI     0.0759
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            31068
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.337
_diffrn_reflns_theta_min         1.920
_diffrn_ambient_temperature      293
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 22.2222
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
scan:
	Number of images: 180
	           Slice: -134.0000 - 46.0000
	     Image width: 1.0000
	        Exp time: 15.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 90.0000
	             XTD: 45.2664
	          2theta: -44.0654
scan:
	Number of images: 177
	           Slice: -134.0000 - 43.0000
	     Image width: 1.0000
	        Exp time: 15.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 270.0000
	             XTD: 45.2664
	          2theta: -44.0654
scan:
	Number of images: 120
	           Slice: -104.0000 - 16.0000
	     Image width: 1.0000
	        Exp time: 15.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 30.0000
	             Phi: 0.0000
	             XTD: 45.2664
	          2theta: -44.0654
scan:
	Number of images: 45
	           Slice: -111.0000 - -66.0000
	     Image width: 1.0000
	        Exp time: 15.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 45.2664
	          2theta: -44.0654
scan:
	Number of images: 180
	           Slice: -180.0000 - 0.0000
	     Image width: 1.0000
	        Exp time: 15.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 120.0000
	             XTD: 45.2664
	          2theta: -90.0654
scan:
	Number of images: 180
	           Slice: -180.0000 - 0.0000
	     Image width: 1.0000
	        Exp time: 15.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 90.0000
	             XTD: 45.2664
	          2theta: -90.0654
scan:
	Number of images: 180
	           Slice: -180.0000 - 0.0000
	     Image width: 1.0000
	        Exp time: 15.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 0.0000
	             XTD: 45.2664
	          2theta: -90.0654
scan:
	Number of images: 180
	           Slice: -180.0000 - 0.0000
	     Image width: 1.0000
	        Exp time: 15.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 270.0000
	             XTD: 45.2664
	          2theta: -90.0654
scan:
	Number of images: 180
	           Slice: -180.0000 - 0.0000
	     Image width: 1.0000
	        Exp time: 15.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 0.0000
	             Phi: 180.0000
	             XTD: 45.2664
	          2theta: -90.0654
scan:
	Number of images: 162
	           Slice: -180.0000 - -18.0000
	     Image width: 1.0000
	        Exp time: 15.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 240.0000
	             XTD: 45.2664
	          2theta: -90.0654
scan:
	Number of images: 156
	           Slice: -180.0000 - -24.0000
	     Image width: 1.0000
	        Exp time: 15.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 180.0000
	             XTD: 45.2664
	          2theta: -90.0654
scan:
	Number of images: 150
	           Slice: -180.0000 - -30.0000
	     Image width: 1.0000
	        Exp time: 15.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 240.0000
	             XTD: 45.2664
	          2theta: -90.0654
scan:
	Number of images: 135
	           Slice: -180.0000 - -45.0000
	     Image width: 1.0000
	        Exp time: 15.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 45.2664
	          2theta: -90.0654
scan:
	Number of images: 110
	           Slice: -180.0000 - -70.0000
	     Image width: 1.0000
	        Exp time: 15.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 45.2664
	          2theta: -90.0654
;
_diffrn_measurement_device       
;
AFC11 (Right): Eulerian 3 circle
;
_diffrn_measurement_device_type  'Rigaku Saturn944+ (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      0.045782
_diffrn_orient_matrix_UB_12      -0.036628
_diffrn_orient_matrix_UB_13      -0.041182
_diffrn_orient_matrix_UB_21      -0.062348
_diffrn_orient_matrix_UB_22      -0.094483
_diffrn_orient_matrix_UB_23      0.014723
_diffrn_orient_matrix_UB_31      -0.033181
_diffrn_orient_matrix_UB_32      0.014181
_diffrn_orient_matrix_UB_33      -0.049511
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           0.9
_diffrn_source_power             0.0
_diffrn_source_voltage           45.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                2834
_reflns_number_total             3622
_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  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 
;
 Flack x determined using 895 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   2.3(10)
_refine_ls_extinction_coef       0.35(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3622
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0795
_refine_ls_restrained_S_all      1.089
_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)+(0.1857P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2400
_refine_ls_wR_factor_ref         0.2659
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C28, O14
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3.a Ternary CH refined with riding coordinates:
 C19(H19), C25(H25)
3.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C21(H21A,H21B)
3.c Aromatic/amide H refined with riding coordinates:
 N4(H4), C12(H12), C13(H13), C22(H22), C23(H23)
3.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C27(H27A,H27B,
 H27C)
;
_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 0.2383(4) 0.3970(3) 0.8364(3) 0.1084(13) Uani 1 1 d . . . . .
O2 O -0.4832(5) 0.5978(3) 0.7201(3) 0.1103(13) Uani 1 1 d . . . . .
O3 O -0.2122(5) 0.5126(4) 0.6767(2) 0.1161(14) Uani 1 1 d . . . . .
N4 N 0.0595(5) 0.2857(3) 0.9583(3) 0.0923(12) Uani 1 1 d . . . . .
H4 H 0.1521 0.2818 0.9756 0.111 Uiso 1 1 calc R . . . .
O5 O -0.1637(5) 0.2090(3) 0.9404(3) 0.1171(14) Uani 1 1 d . . . . .
O6 O -0.5327(5) 0.6528(4) 0.8750(3) 0.1207(14) Uani 1 1 d . . . . .
C7 C -0.3683(7) 0.5862(4) 0.7776(3) 0.0936(13) Uani 1 1 d . . . . .
C8 C 0.0264(6) 0.4834(4) 0.7922(3) 0.0912(13) Uani 1 1 d . . . . .
C9 C -0.1353(6) 0.5640(3) 0.8932(3) 0.0883(12) Uani 1 1 d . . . . .
C10 C -0.0294(6) 0.2097(4) 0.9659(4) 0.0927(13) Uani 1 1 d . . . . .
C11 C -0.1158(6) 0.5307(3) 0.8133(3) 0.0841(12) Uani 1 1 d . . . . .
C12 C 0.0311(7) 0.3131(5) 0.7774(3) 0.1032(16) Uani 1 1 d . . . . .
H12 H -0.0573 0.2782 0.7878 0.124 Uiso 1 1 calc R . . . .
C13 C -0.2745(7) 0.6048(4) 0.9154(3) 0.0959(14) Uani 1 1 d . . . . .
H13 H -0.2888 0.6253 0.9691 0.115 Uiso 1 1 calc R . . . .
O14 O 0.3107(8) 0.3539(5) 0.6252(4) 0.156(2) Uani 1 1 d . U . . .
C15 C -0.3917(7) 0.6155(4) 0.8594(3) 0.0966(14) Uani 1 1 d . . . . .
C16 C 0.0758(6) 0.3901(4) 0.8360(4) 0.0908(14) Uani 1 1 d . . . . .
C17 C -0.2332(7) 0.5429(4) 0.7567(3) 0.0912(13) Uani 1 1 d . . . . .
C18 C -0.0029(8) 0.5575(4) 0.9516(4) 0.0991(15) Uani 1 1 d . . . . .
H18A H -0.0245 0.5982 0.9984 0.119 Uiso 1 1 calc R . . . .
H18B H 0.0867 0.5832 0.9245 0.119 Uiso 1 1 calc R . . . .
C19 C 0.0092(6) 0.3758(3) 0.9224(3) 0.0863(12) Uani 1 1 d . . . . .
H19 H -0.1017 0.3705 0.9156 0.104 Uiso 1 1 calc R . . . .
C20 C 0.0394(8) 0.1226(5) 1.0076(5) 0.1157(19) Uani 1 1 d . . . . .
H20A H 0.0363 0.0690 0.9708 0.174 Uiso 1 1 calc GR . . . .
H20B H -0.0179 0.1079 1.0560 0.174 Uiso 1 1 calc GR . . . .
H20C H 0.1434 0.1360 1.0222 0.174 Uiso 1 1 calc GR . . . .
C21 C 0.0355(8) 0.4575(4) 0.9831(4) 0.1041(16) Uani 1 1 d . . . . .
H21A H -0.0252 0.4452 1.0317 0.125 Uiso 1 1 calc R . . . .
H21B H 0.1420 0.4567 0.9995 0.125 Uiso 1 1 calc R . . . .
C22 C 0.1469(8) 0.5086(4) 0.7445(4) 0.1052(17) Uani 1 1 d . . . . .
H22 H 0.1527 0.5625 0.7112 0.126 Uiso 1 1 calc R . . . .
C23 C 0.1134(10) 0.2921(5) 0.7102(5) 0.118(2) Uani 1 1 d . . . . .
H23 H 0.0926 0.2388 0.6779 0.142 Uiso 1 1 calc R . . . .
C24 C -0.4966(11) 0.6904(5) 0.6882(6) 0.136(2) Uani 1 1 d . . . . .
H24A H -0.3990 0.7115 0.6685 0.205 Uiso 1 1 calc GR . . . .
H24B H -0.5314 0.7331 0.7304 0.205 Uiso 1 1 calc GR . . . .
H24C H -0.5686 0.6902 0.6439 0.205 Uiso 1 1 calc GR . . . .
C25 C 0.2660(8) 0.4359(5) 0.7547(5) 0.115(2) Uani 1 1 d . . . . .
H25 H 0.3688 0.4629 0.7493 0.138 Uiso 1 1 calc R . . . .
C26 C -0.2888(11) 0.4258(6) 0.6572(5) 0.129(2) Uani 1 1 d . . . . .
H26A H -0.2670 0.4085 0.6015 0.194 Uiso 1 1 calc GR . . . .
H26B H -0.3968 0.4345 0.6638 0.194 Uiso 1 1 calc GR . . . .
H26C H -0.2543 0.3759 0.6931 0.194 Uiso 1 1 calc GR . . . .
C27 C -0.5656(10) 0.6746(6) 0.9568(6) 0.137(3) Uani 1 1 d . . . . .
H27A H -0.6665 0.7011 0.9605 0.205 Uiso 1 1 calc GR . . . .
H27B H -0.4929 0.7204 0.9769 0.205 Uiso 1 1 calc GR . . . .
H27C H -0.5601 0.6173 0.9892 0.205 Uiso 1 1 calc GR . . . .
C28 C 0.2352(9) 0.3572(5) 0.6918(5) 0.1165(18) Uani 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C16 1.427(7) . ?
O1 C25 1.460(8) . ?
O2 C7 1.386(7) . ?
O2 C24 1.398(8) . ?
O3 C17 1.385(7) . ?
O3 C26 1.420(9) . ?
N4 C10 1.323(7) . ?
N4 C19 1.456(7) . ?
O5 C10 1.247(7) . ?
O6 C15 1.364(8) . ?
O6 C27 1.399(10) . ?
C7 C15 1.411(8) . ?
C7 C17 1.372(8) . ?
C8 C11 1.451(8) . ?
C8 C16 1.547(8) . ?
C8 C22 1.358(8) . ?
C9 C11 1.396(7) . ?
C9 C13 1.393(8) . ?
C9 C18 1.503(7) . ?
C10 C20 1.517(8) . ?
C11 C17 1.393(8) . ?
C12 C16 1.490(9) . ?
C12 C23 1.345(10) . ?
C13 C15 1.383(8) . ?
O14 C28 1.273(9) . ?
C16 C19 1.540(8) . ?
C18 C21 1.525(8) . ?
C19 C21 1.528(8) . ?
C22 C25 1.465(10) . ?
C23 C28 1.434(11) . ?
C25 C28 1.528(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 O1 C25 100.8(5) . . ?
C7 O2 C24 114.9(5) . . ?
C17 O3 C26 114.1(5) . . ?
C10 N4 C19 123.5(4) . . ?
C15 O6 C27 116.6(6) . . ?
O2 C7 C15 120.1(5) . . ?
C17 C7 O2 120.6(5) . . ?
C17 C7 C15 119.3(5) . . ?
C11 C8 C16 120.9(4) . . ?
C22 C8 C11 133.3(5) . . ?
C22 C8 C16 105.4(5) . . ?
C11 C9 C18 118.6(5) . . ?
C13 C9 C11 119.1(5) . . ?
C13 C9 C18 122.3(5) . . ?
N4 C10 C20 116.8(5) . . ?
O5 C10 N4 122.0(5) . . ?
O5 C10 C20 121.2(5) . . ?
C9 C11 C8 118.5(5) . . ?
C17 C11 C8 122.2(4) . . ?
C17 C11 C9 119.3(5) . . ?
C23 C12 C16 122.7(6) . . ?
C15 C13 C9 121.5(5) . . ?
O6 C15 C7 114.8(5) . . ?
O6 C15 C13 126.1(5) . . ?
C13 C15 C7 119.1(5) . . ?
O1 C16 C8 102.9(4) . . ?
O1 C16 C12 108.3(4) . . ?
O1 C16 C19 112.5(5) . . ?
C12 C16 C8 103.8(5) . . ?
C12 C16 C19 113.2(4) . . ?
C19 C16 C8 115.2(4) . . ?
O3 C17 C11 119.3(5) . . ?
C7 C17 O3 118.9(5) . . ?
C7 C17 C11 121.7(5) . . ?
C9 C18 C21 116.0(5) . . ?
N4 C19 C16 111.5(4) . . ?
N4 C19 C21 109.7(4) . . ?
C21 C19 C16 116.1(5) . . ?
C18 C21 C19 115.5(5) . . ?
C8 C22 C25 108.1(5) . . ?
C12 C23 C28 115.6(6) . . ?
O1 C25 C22 104.0(5) . . ?
O1 C25 C28 108.5(5) . . ?
C22 C25 C28 107.2(6) . . ?
O14 C28 C23 122.9(7) . . ?
O14 C28 C25 120.5(7) . . ?
C23 C28 C25 116.5(6) . . ?

_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_a
_audit_block_doi                 10.5517/ccdc.csd.cc1n56z0
_database_code_depnum_ccdc_archive 'CCDC 1524362'
_audit_update_record             
;
2016-12-24 deposited with the CCDC.
2017-05-05 downloaded from the CCDC.
;
_audit_creation_date             2016-12-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r1)
;
_chemical_name_common            ?
_chemical_name_systematic        liux-1
_chemical_formula_moiety         'C36 H31 N3 O12, C4 H5 O2'
_chemical_formula_sum            'C40 H36 N3 O14'
_chemical_formula_weight         782.72
_chemical_absolute_configuration unk
_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   13.869(9)
_cell_length_b                   9.736(8)
_cell_length_c                   14.969(11)
_cell_angle_alpha                90
_cell_angle_beta                 105.103(18)
_cell_angle_gamma                90
_cell_volume                     1951(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1874
_cell_measurement_temperature    293
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      23.3
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.593
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    "'not measured'"
_exptl_crystal_description       Prism
_exptl_crystal_F_000             818
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0860
_diffrn_reflns_av_unetI/netI     0.0867
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12514
_diffrn_reflns_point_group_measured_fraction_full 0.857
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.361
_diffrn_reflns_theta_min         1.409
_diffrn_ambient_temperature      293
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 22.2222
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
scan:
	Number of images: 180
	           Slice: -134.0000 - 46.0000
	     Image width: 1.0000
	        Exp time: 6.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 30.0000
	             Phi: 0.0000
	             XTD: 44.8868
	          2theta: -44.3414
scan:
	Number of images: 180
	           Slice: -134.0000 - 46.0000
	     Image width: 1.0000
	        Exp time: 6.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 240.0000
	             XTD: 44.8868
	          2theta: -44.3414
scan:
	Number of images: 150
	           Slice: -180.0000 - -30.0000
	     Image width: 1.0000
	        Exp time: 6.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 30.0000
	             Phi: 0.0000
	             XTD: 44.8868
	          2theta: -90.3414
scan:
	Number of images: 150
	           Slice: -180.0000 - -30.0000
	     Image width: 1.0000
	        Exp time: 6.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 240.0000
	             XTD: 44.8868
	          2theta: -90.3414
scan:
	Number of images: 132
	           Slice: -180.0000 - -48.0000
	     Image width: 1.0000
	        Exp time: 6.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 120.0000
	             XTD: 44.8868
	          2theta: -90.3414
scan:
	Number of images: 129
	           Slice: -147.0000 - -18.0000
	     Image width: 1.0000
	        Exp time: 6.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 270.0000
	             XTD: 44.8868
	          2theta: -90.3414
;
_diffrn_measurement_device       
;
AFC11 (Right): Eulerian 3 circle
;
_diffrn_measurement_device_type  'Rigaku Saturn944+ (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      -0.004748
_diffrn_orient_matrix_UB_12      -0.041846
_diffrn_orient_matrix_UB_13      -0.061679
_diffrn_orient_matrix_UB_21      -0.059132
_diffrn_orient_matrix_UB_22      -0.067315
_diffrn_orient_matrix_UB_23      0.050222
_diffrn_orient_matrix_UB_31      -0.055605
_diffrn_orient_matrix_UB_32      0.023737
_diffrn_orient_matrix_UB_33      -0.033655
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           0.9
_diffrn_source_power             0.0
_diffrn_source_voltage           45.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.637
_reflns_Friedel_fraction_full    0.714
_reflns_Friedel_fraction_max     0.707
_reflns_number_gt                3344
_reflns_number_total             6095
_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  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 
;
 Flack x determined using 1025 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(10)
_refine_ls_extinction_coef       0.38(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     515
_refine_ls_number_reflns         6095
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1221
_refine_ls_R_factor_gt           0.0992
_refine_ls_restrained_S_all      1.023
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2557
_refine_ls_wR_factor_ref         0.3148
_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:
 C14(H14A,H14B), C32(H32A,H32B), C41(H41A,H41B), C51(H51A,H51B)
2.c Me refined with riding coordinates:
 C44(H44A,H44B,H44C), C45(H45A,H45B,H45C), C47(H47A,H47B,H47C), C48(H48A,H48B,
 H48C), C52(H52A,H52B,H52C)
2.d Aromatic/amide H refined with riding coordinates:
 C9(H9), C17(H17), C19(H19), C22(H22), C23(H23), C26(H26), C30(H30), C36(H36),
 C37(H37), C40(H40), C43(H43), C46(H46)
;
_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
O3 O -0.3484(5) -0.3467(7) -0.6914(5) 0.107(2) Uani 1 1 d . . . . .
O2 O 0.2629(4) -0.5687(6) -0.7993(4) 0.0936(17) Uani 1 1 d . . . . .
C3 C 0.1240(6) -0.2978(8) -0.6571(5) 0.0784(19) Uani 1 1 d . . . . .
O4 O 0.3659(5) -0.3535(9) -0.7132(5) 0.116(2) Uani 1 1 d . . . . .
O7 O -0.3014(5) -0.7431(6) -0.6163(5) 0.1003(18) Uani 1 1 d . . . . .
C6 C 0.2203(5) -0.4836(9) -0.7472(6) 0.081(2) Uani 1 1 d . . . . .
C7 C -0.0553(6) -0.1936(8) -0.7662(5) 0.0761(19) Uani 1 1 d . . . . .
H7 H -0.0052 -0.2320 -0.7947 0.091 Uiso 1 1 calc R . . . .
C8 C -0.0339(5) -0.4314(8) -0.7002(6) 0.0762(19) Uani 1 1 d . . . . .
C9 C -0.1968(6) -0.3035(8) -0.7242(6) 0.084(2) Uani 1 1 d . . . . .
H9 H -0.2250 -0.2190 -0.7451 0.100 Uiso 1 1 calc R . . . .
C10 C -0.2435(6) -0.5344(8) -0.6691(6) 0.082(2) Uani 1 1 d . . . . .
N1 N -0.1256(5) -0.1201(7) -0.8401(5) 0.0838(18) Uani 1 1 d . . . . .
C12 C -0.2570(9) -1.2048(10) -0.4898(6) 0.098(3) Uani 1 1 d . . . . .
O5 O -0.1815(6) 0.0434(8) -0.7562(5) 0.113(2) Uani 1 1 d . . . . .
C14 C 0.0717(6) -0.1924(9) -0.6145(5) 0.085(2) Uani 1 1 d . . . . .
H14A H 0.1209 -0.1347 -0.5734 0.103 Uiso 1 1 calc R . . . .
H14B H 0.0331 -0.2381 -0.5777 0.103 Uiso 1 1 calc R . . . .
C15 C -0.3270(7) -0.9507(9) -0.5513(6) 0.084(2) Uani 1 1 d . . . . .
C16 C 0.1206(6) -0.5056(8) -0.7454(6) 0.082(2) Uani 1 1 d . . . . .
C17 C -0.2314(7) -0.9891(10) -0.5513(6) 0.092(2) Uani 1 1 d . . . . .
H17 H -0.1905 -0.9288 -0.5728 0.110 Uiso 1 1 calc R . . . .
C18 C 0.0732(5) -0.4127(9) -0.6999(6) 0.079(2) Uani 1 1 d . . . . .
C19 C 0.2235(6) -0.2780(9) -0.6590(6) 0.088(2) Uani 1 1 d . . . . .
H19 H 0.2587 -0.2024 -0.6292 0.106 Uiso 1 1 calc R . . . .
O1 O 0.0693(5) -0.6118(8) -0.7902(7) 0.128(3) Uani 1 1 d . . . . .
O9 O -0.1122(7) 0.4367(9) -1.1365(6) 0.134(3) Uani 1 1 d . . . . .
C22 C -0.1558(6) -0.6020(10) -0.6608(7) 0.092(2) Uani 1 1 d . . . . .
H22 H -0.1572 -0.6948 -0.6463 0.110 Uiso 1 1 calc R . . . .
C23 C -0.3875(8) -1.0440(11) -0.5193(7) 0.099(3) Uani 1 1 d . . . . .
H23 H -0.4516 -1.0185 -0.5175 0.119 Uiso 1 1 calc R . . . .
C24 C -0.2631(6) -0.3929(10) -0.6934(6) 0.089(2) Uani 1 1 d . . . . .
C25 C -0.1804(8) 0.3153(11) -1.0330(7) 0.101(3) Uani 1 1 d . . . . .
C26 C -0.1960(8) -1.1185(11) -0.5188(7) 0.100(3) Uani 1 1 d . . . . .
H26 H -0.1311 -1.1448 -0.5173 0.120 Uiso 1 1 calc R . . . .
O8 O -0.4487(5) -0.7720(9) -0.5821(6) 0.126(3) Uani 1 1 d . . . . .
C28 C -0.1011(5) -0.3170(8) -0.7291(5) 0.0765(19) Uani 1 1 d . . . . .
O6 O -0.1152(5) -0.3019(8) -0.9322(5) 0.109(2) Uani 1 1 d . . . . .
C30 C -0.0618(6) -0.5540(10) -0.6706(7) 0.094(2) Uani 1 1 d . . . . .
H30 H -0.0103 -0.6178 -0.6539 0.112 Uiso 1 1 calc R . . . .
C31 C -0.1606(7) -0.1992(12) -0.9230(6) 0.097(2) Uani 1 1 d . . . . .
C32 C 0.0030(6) -0.1034(9) -0.6864(6) 0.088(2) Uani 1 1 d . . . . .
H32A H 0.0419 -0.0359 -0.7096 0.106 Uiso 1 1 calc R . . . .
H32B H -0.0431 -0.0549 -0.6588 0.106 Uiso 1 1 calc R . . . .
O10 O -0.2582(7) 0.4971(10) -1.1232(7) 0.151(4) Uani 1 1 d . . . . .
C34 C 0.2695(5) -0.3695(10) -0.7044(6) 0.086(2) Uani 1 1 d . . . . .
C35 C -0.3653(8) -0.8164(10) -0.5832(7) 0.097(3) Uani 1 1 d . . . . .
C36 C -0.2376(8) 0.3292(10) -0.9713(7) 0.103(3) Uani 1 1 d . . . . .
H36 H -0.2787 0.4052 -0.9728 0.123 Uiso 1 1 calc R . . . .
C37 C -0.2319(8) 0.2255(11) -0.9065(7) 0.104(3) Uani 1 1 d . . . . .
H37 H -0.2697 0.2322 -0.8637 0.125 Uiso 1 1 calc R . . . .
C38 C -0.1713(6) 0.1126(9) -0.9044(6) 0.088(2) Uani 1 1 d . . . . .
C39 C -0.1627(7) 0.0100(10) -0.8298(7) 0.092(2) Uani 1 1 d . . . . .
C40 C -0.1174(8) 0.2044(10) -1.0329(8) 0.103(3) Uani 1 1 d . . . . .
H40 H -0.0794 0.1991 -1.0756 0.123 Uiso 1 1 calc R . . . .
C41 C -0.3326(7) -0.6080(11) -0.6479(9) 0.105(3) Uani 1 1 d . . . . .
H41A H -0.3548 -0.5583 -0.6007 0.126 Uiso 1 1 calc R . . . .
H41B H -0.3877 -0.6126 -0.7032 0.126 Uiso 1 1 calc R . . . .
N2 N -0.1851(8) 0.4252(9) -1.1033(6) 0.110(3) Uani 1 1 d . . . . .
C43 C -0.1126(8) 0.1048(10) -0.9695(7) 0.098(3) Uani 1 1 d . . . . .
H43 H -0.0706 0.0300 -0.9682 0.118 Uiso 1 1 calc R . . . .
C44 C 0.4215(7) -0.2385(15) -0.6712(8) 0.128(4) Uani 1 1 d . . . . .
H44A H 0.4864 -0.2404 -0.6828 0.192 Uiso 1 1 calc R . . . .
H44B H 0.3874 -0.1558 -0.6966 0.192 Uiso 1 1 calc R . . . .
H44C H 0.4286 -0.2409 -0.6057 0.192 Uiso 1 1 calc R . . . .
C45 C -0.2569(8) -0.1613(12) -0.9885(7) 0.112(3) Uani 1 1 d . . . . .
H45A H -0.2806 -0.0767 -0.9690 0.168 Uiso 1 1 calc R . . . .
H45B H -0.2475 -0.1502 -1.0494 0.168 Uiso 1 1 calc R . . . .
H45C H -0.3050 -0.2325 -0.9895 0.168 Uiso 1 1 calc R . . . .
C46 C -0.3532(10) -1.1704(12) -0.4913(7) 0.112(3) Uani 1 1 d . . . . .
H46 H -0.3945 -1.2339 -0.4730 0.135 Uiso 1 1 calc R . . . .
N3 N -0.2195(14) -1.3413(13) -0.4582(7) 0.140(4) Uani 1 1 d . . . . .
C47 C 0.3402(11) -0.6592(16) -0.7502(10) 0.151(5) Uani 1 1 d . . . . .
H47A H 0.3640 -0.7133 -0.7936 0.227 Uiso 1 1 calc R . . . .
H47B H 0.3942 -0.6061 -0.7129 0.227 Uiso 1 1 calc R . . . .
H47C H 0.3140 -0.7188 -0.7111 0.227 Uiso 1 1 calc R . . . .
O11 O -0.1345(13) -1.3675(13) -0.4560(10) 0.191(5) Uani 1 1 d . . . . .
O12 O -0.2741(12) -1.4243(11) -0.4335(9) 0.176(4) Uani 1 1 d . . . . .
C48 C 0.078(3) -0.710(4) -0.818(3) 0.41(3) Uani 1 1 d . . . . .
H48A H 0.0138 -0.7491 -0.8456 0.613 Uiso 1 1 calc R . . . .
H48B H 0.1149 -0.7012 -0.8639 0.613 Uiso 1 1 calc R . . . .
H48C H 0.1142 -0.7692 -0.7691 0.613 Uiso 1 1 calc R . . . .
O13 O -0.4644(9) 0.0476(16) -0.9577(8) 0.177(4) Uani 1 1 d . . . . .
C49 C -0.5077(15) 0.060(4) -1.0485(17) 0.214(11) Uani 1 1 d . . . . .
C50 C -0.4628(16) 0.086(4) -1.1112(15) 0.218(11) Uani 1 1 d . . . . .
C51 C -0.4959(18) 0.066(7) -0.8881(13) 0.45(4) Uani 1 1 d . . . . .
H51A H -0.4980 0.1642 -0.8796 0.543 Uiso 1 1 calc R . . . .
H51B H -0.5647 0.0344 -0.9047 0.543 Uiso 1 1 calc R . . . .
C52 C -0.4584(18) 0.018(4) -0.8132(18) 0.252(14) Uani 1 1 d . . . . .
H52A H -0.4960 0.0465 -0.7708 0.378 Uiso 1 1 calc R . . . .
H52B H -0.4583 -0.0799 -0.8170 0.378 Uiso 1 1 calc R . . . .
H52C H -0.3910 0.0511 -0.7917 0.378 Uiso 1 1 calc R . . . .
O14 O -0.582(3) 0.007(6) -1.0673(18) 0.50(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C24 1.274(10) . ?
O2 C6 1.373(9) . ?
O2 C47 1.433(13) . ?
C3 C14 1.493(12) . ?
C3 C18 1.387(11) . ?
C3 C19 1.400(11) . ?
O4 C34 1.386(9) . ?
O4 C44 1.411(14) . ?
O7 C35 1.330(10) . ?
O7 C41 1.427(12) . ?
C6 C16 1.406(10) . ?
C6 C34 1.371(12) . ?
C7 N1 1.457(10) . ?
C7 C28 1.528(11) . ?
C7 C32 1.534(11) . ?
C8 C18 1.495(10) . ?
C8 C28 1.444(10) . ?
C8 C30 1.363(12) . ?
C9 C24 1.426(12) . ?
C9 C28 1.356(11) . ?
C10 C22 1.360(11) . ?
C10 C24 1.432(13) . ?
C10 C41 1.532(12) . ?
N1 C31 1.433(13) . ?
N1 C39 1.391(12) . ?
C12 C26 1.342(14) . ?
C12 C46 1.370(15) . ?
C12 N3 1.460(16) . ?
O5 C39 1.241(11) . ?
C14 C32 1.511(12) . ?
C15 C17 1.377(12) . ?
C15 C23 1.404(13) . ?
C15 C35 1.445(13) . ?
C16 C18 1.396(11) . ?
C16 O1 1.333(11) . ?
C17 C26 1.393(14) . ?
C19 C34 1.374(13) . ?
O1 C48 1.06(3) . ?
O9 N2 1.242(11) . ?
C22 C30 1.428(11) . ?
C23 C46 1.346(16) . ?
C25 C36 1.372(13) . ?
C25 C40 1.389(13) . ?
C25 N2 1.490(13) . ?
O8 C35 1.239(12) . ?
O6 C31 1.208(12) . ?
C31 C45 1.484(13) . ?
O10 N2 1.205(11) . ?
C36 C37 1.388(13) . ?
C37 C38 1.379(13) . ?
C38 C39 1.479(12) . ?
C38 C43 1.425(12) . ?
C40 C43 1.347(13) . ?
N3 O11 1.198(16) . ?
N3 O12 1.228(16) . ?
O13 C49 1.34(2) . ?
O13 C51 1.24(2) . ?
C49 C50 1.28(3) . ?
C49 O14 1.12(3) . ?
C51 C52 1.20(4) . ?

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
C6 O2 C47 117.0(7) . . ?
C18 C3 C14 120.4(7) . . ?
C18 C3 C19 119.1(7) . . ?
C19 C3 C14 120.3(8) . . ?
C34 O4 C44 118.4(8) . . ?
C35 O7 C41 116.4(8) . . ?
O2 C6 C16 119.3(7) . . ?
C34 C6 O2 121.3(6) . . ?
C34 C6 C16 119.1(7) . . ?
N1 C7 C28 113.8(6) . . ?
N1 C7 C32 115.0(7) . . ?
C28 C7 C32 110.6(6) . . ?
C28 C8 C18 118.0(7) . . ?
C30 C8 C18 118.1(7) . . ?
C30 C8 C28 123.9(7) . . ?
C28 C9 C24 132.9(8) . . ?
C22 C10 C24 126.5(8) . . ?
C22 C10 C41 120.4(8) . . ?
C24 C10 C41 113.1(7) . . ?
C31 N1 C7 113.7(7) . . ?
C39 N1 C7 123.8(7) . . ?
C39 N1 C31 122.3(8) . . ?
C26 C12 C46 122.4(9) . . ?
C26 C12 N3 118.3(12) . . ?
C46 C12 N3 119.4(12) . . ?
C3 C14 C32 112.1(7) . . ?
C17 C15 C23 119.0(9) . . ?
C17 C15 C35 121.2(8) . . ?
C23 C15 C35 119.8(9) . . ?
C18 C16 C6 120.0(7) . . ?
O1 C16 C6 120.5(7) . . ?
O1 C16 C18 119.4(7) . . ?
C15 C17 C26 119.9(9) . . ?
C3 C18 C8 119.0(7) . . ?
C3 C18 C16 120.1(7) . . ?
C16 C18 C8 120.9(7) . . ?
C34 C19 C3 120.5(8) . . ?
C48 O1 C16 142.5(19) . . ?
C10 C22 C30 130.6(8) . . ?
C46 C23 C15 120.2(10) . . ?
O3 C24 C9 118.2(8) . . ?
O3 C24 C10 116.7(8) . . ?
C9 C24 C10 125.0(8) . . ?
C36 C25 C40 123.4(9) . . ?
C36 C25 N2 118.6(9) . . ?
C40 C25 N2 118.0(9) . . ?
C12 C26 C17 118.9(10) . . ?
C8 C28 C7 114.8(6) . . ?
C9 C28 C7 116.7(7) . . ?
C9 C28 C8 128.5(7) . . ?
C8 C30 C22 131.6(8) . . ?
N1 C31 C45 118.8(9) . . ?
O6 C31 N1 118.3(9) . . ?
O6 C31 C45 122.5(10) . . ?
C14 C32 C7 109.5(7) . . ?
C6 C34 O4 114.9(7) . . ?
C6 C34 C19 121.2(7) . . ?
C19 C34 O4 123.9(8) . . ?
O7 C35 C15 112.6(9) . . ?
O8 C35 O7 122.2(10) . . ?
O8 C35 C15 125.1(8) . . ?
C25 C36 C37 117.4(9) . . ?
C38 C37 C36 121.3(9) . . ?
C37 C38 C39 119.0(8) . . ?
C37 C38 C43 118.7(8) . . ?
C43 C38 C39 122.1(8) . . ?
N1 C39 C38 119.4(8) . . ?
O5 C39 N1 120.4(8) . . ?
O5 C39 C38 119.9(9) . . ?
C43 C40 C25 118.4(9) . . ?
O7 C41 C10 108.0(7) . . ?
O9 N2 C25 117.2(9) . . ?
O10 N2 O9 124.7(9) . . ?
O10 N2 C25 118.1(9) . . ?
C40 C43 C38 120.8(9) . . ?
C23 C46 C12 119.5(10) . . ?
O11 N3 C12 117.8(15) . . ?
O11 N3 O12 122.1(14) . . ?
O12 N3 C12 120.1(15) . . ?
C51 O13 C49 132.5(18) . . ?
C50 C49 O13 126.0(18) . . ?
O14 C49 O13 111(2) . . ?
O14 C49 C50 120(3) . . ?
C52 C51 O13 125(4) . . ?

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