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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_17junb_0m
_database_code_depnum_ccdc_archive 'CCDC 1562218'
_audit_update_record             
;
2017-07-14 deposited with the CCDC.
2018-03-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H30 N2 O4'
_chemical_formula_sum            'C30 H30 N2 O4'
_chemical_formula_weight         482.56

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.795(5)
_cell_length_b                   10.469(5)
_cell_length_c                   12.397(5)
_cell_angle_alpha                87.898(5)
_cell_angle_beta                 81.097(5)
_cell_angle_gamma                82.861(5)
_cell_volume                     1246.0(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6199
_cell_measurement_theta_min      2.1
_cell_measurement_theta_max      28.3

_exptl_crystal_description       PRISM
_exptl_crystal_colour            WHITE
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19105
_diffrn_reflns_av_R_equivalents  0.1514
_diffrn_reflns_av_sigmaI/netI    0.2671
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         28.34
_reflns_number_total             6199
_reflns_number_gt                2583
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART APEX'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT PLUS'
_computing_structure_solution    'SIR97(Altomare, et. al. 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'WingX publication routine (Farrugia, 1999)'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0790P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6199
_refine_ls_number_parameters     327
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.2425
_refine_ls_R_factor_gt           0.0870
_refine_ls_wR_factor_ref         0.1989
_refine_ls_wR_factor_gt          0.1476
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      1.434
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.7065(4) 0.3172(3) 0.4508(3) 0.0247(9) Uani 1 1 d . . .
O002 O 0.6165(4) -0.1151(3) 0.1030(3) 0.0287(10) Uani 1 1 d . . .
O003 O 0.7302(4) 0.0592(3) 0.0677(3) 0.0312(10) Uani 1 1 d . . .
O004 O 0.5147(3) 0.2641(3) 0.5579(3) 0.0251(9) Uani 1 1 d . . .
N005 N 0.8981(4) -0.1453(4) 0.4557(3) 0.0192(10) Uani 1 1 d . . .
N006 N 0.6096(4) 0.3342(4) 0.1920(3) 0.0165(10) Uani 1 1 d . . .
C007 C 0.3755(5) 0.3689(5) 0.2230(4) 0.0194(12) Uani 1 1 d . . .
C008 C 0.6613(5) -0.0095(4) 0.2535(4) 0.0179(12) Uani 1 1 d . . .
H008 H 0.5754 -0.0441 0.2860 0.021 Uiso 1 1 calc R . .
C009 C 0.7746(5) 0.0033(5) 0.5708(4) 0.0188(12) Uani 1 1 d . . .
C010 C 0.8005(5) -0.0753(5) 0.4019(4) 0.0180(12) Uani 1 1 d . . .
C011 C 0.7404(5) 0.0643(5) 0.6716(4) 0.0195(12) Uani 1 1 d . . .
H011 H 0.6706 0.1336 0.6812 0.023 Uiso 1 1 calc R . .
C2 C 0.9299(5) -0.3793(5) 0.4259(4) 0.0239(13) Uani 1 1 d D . .
H2 H 0.9834 -0.4527 0.3957 0.029 Uiso 1 1 calc R . .
C013 C 0.6581(5) 0.1271(4) 0.2987(4) 0.0174(12) Uani 1 1 d . . .
H013 H 0.7526 0.1517 0.2822 0.021 Uiso 1 1 calc R . .
C014 C 0.6203(5) 0.1170(4) 0.4242(4) 0.0165(12) Uani 1 1 d . . .
H014 H 0.5273 0.0894 0.4425 0.020 Uiso 1 1 calc R . .
C015 C 0.5621(5) 0.2296(5) 0.2523(4) 0.0171(12) Uani 1 1 d . . .
C016 C 0.4963(5) 0.4207(5) 0.1747(4) 0.0189(12) Uani 1 1 d . . .
C017 C 0.2452(5) 0.4414(5) 0.2180(4) 0.0267(14) Uani 1 1 d . . .
H017 H 0.1631 0.4093 0.2484 0.032 Uiso 1 1 calc R . .
C018 C 0.4198(5) 0.2488(5) 0.2711(4) 0.0205(12) Uani 1 1 d . . .
H018 H 0.3620 0.1928 0.3089 0.025 Uiso 1 1 calc R . .
C019 C 0.6212(5) 0.2443(5) 0.4760(4) 0.0186(12) Uani 1 1 d . . .
C020 C 0.8107(5) 0.0212(5) 0.7566(4) 0.0259(13) Uani 1 1 d . . .
H020 H 0.7877 0.0617 0.8236 0.031 Uiso 1 1 calc R . .
C021 C 0.9926(5) -0.2548(5) 0.4126(4) 0.0231(13) Uani 1 1 d D . .
H212 H 1.0740 -0.2629 0.4492 0.028 Uiso 1 1 calc R . .
H211 H 1.0233 -0.2392 0.3355 0.028 Uiso 1 1 calc R . .
C022 C 0.4928(5) 0.5408(5) 0.1226(4) 0.0218(13) Uani 1 1 d . . .
H022 H 0.5740 0.5728 0.0900 0.026 Uiso 1 1 calc R . .
C023 C 0.2420(5) 0.5598(5) 0.1675(4) 0.0270(14) Uani 1 1 d . . .
H023 H 0.1565 0.6082 0.1639 0.032 Uiso 1 1 calc R . .
C024 C 0.7247(5) 0.0182(5) 0.4676(4) 0.0165(12) Uani 1 1 d . . .
C025 C 0.7533(5) 0.3510(5) 0.1453(4) 0.0224(13) Uani 1 1 d D . .
H215 H 0.7566 0.3750 0.0687 0.027 Uiso 1 1 calc R . .
H214 H 0.8115 0.2696 0.1497 0.027 Uiso 1 1 calc R . .
C026 C 0.5115(6) 0.3768(5) 0.6236(4) 0.0361(16) Uani 1 1 d . . .
H220 H 0.6001 0.3770 0.6476 0.054 Uiso 1 1 calc R . .
H026 H 0.4401 0.3748 0.6859 0.054 Uiso 1 1 calc R . .
H02C H 0.4922 0.4532 0.5806 0.054 Uiso 1 1 calc R . .
C027 C 0.8828(5) -0.1002(5) 0.5601(4) 0.0195(12) Uani 1 1 d . . .
C1 C 0.8113(5) 0.4516(5) 0.2020(5) 0.0269(14) Uani 1 1 d D . .
H1 H 0.8092 0.4452 0.2772 0.032 Uiso 1 1 calc R . .
C029 C 0.6724(5) -0.0136(5) 0.1312(4) 0.0215(13) Uani 1 1 d . . .
C030 C 0.9162(5) -0.0825(5) 0.7436(4) 0.0273(14) Uani 1 1 d . . .
H030 H 0.9623 -0.1098 0.8021 0.033 Uiso 1 1 calc R . .
C031 C 0.3642(6) 0.6102(5) 0.1211(4) 0.0259(13) Uani 1 1 d . . .
H031 H 0.3583 0.6919 0.0888 0.031 Uiso 1 1 calc R . .
C032 C 0.9529(5) -0.1447(5) 0.6457(4) 0.0236(13) Uani 1 1 d . . .
H032 H 1.0223 -0.2143 0.6371 0.028 Uiso 1 1 calc R . .
C033 C 0.8018(6) -0.3916(5) 0.4785(4) 0.0291(14) Uani 1 1 d D . .
H213 H 0.7457 -0.3201 0.5096 0.035 Uiso 1 1 calc R . .
H221 H 0.7691 -0.4716 0.4839 0.035 Uiso 1 1 calc R . .
C034 C 0.8635(6) 0.5460(5) 0.1495(5) 0.0379(16) Uani 1 1 d D . .
H219 H 0.8662 0.5536 0.0742 0.045 Uiso 1 1 calc R . .
H03D H 0.8988 0.6071 0.1866 0.045 Uiso 1 1 calc R . .
C035 C 0.7852(5) -0.0990(5) 0.2862(4) 0.0210(13) Uani 1 1 d . . .
H03E H 0.7706 -0.1880 0.2788 0.025 Uiso 1 1 calc R . .
H03F H 0.8697 -0.0834 0.2381 0.025 Uiso 1 1 calc R . .
C036 C 0.6353(6) -0.1406(5) -0.0130(4) 0.0353(16) Uani 1 1 d . . .
H218 H 0.6107 -0.0626 -0.0523 0.053 Uiso 1 1 calc R . .
H217 H 0.5769 -0.2039 -0.0259 0.053 Uiso 1 1 calc R . .
H216 H 0.7309 -0.1724 -0.0375 0.053 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
O001 C019 1.199(5) . ?
O002 C029 1.335(6) . ?
O002 C036 1.451(6) . ?
O003 C029 1.203(6) . ?
O004 C019 1.341(6) . ?
O004 C026 1.452(6) . ?
N005 C010 1.371(6) . ?
N005 C027 1.374(6) . ?
N005 C021 1.444(6) . ?
N006 C016 1.382(6) . ?
N006 C015 1.390(6) . ?
N006 C025 1.466(6) . ?
C007 C016 1.403(7) . ?
C007 C017 1.411(7) . ?
C007 C018 1.419(7) . ?
C008 C029 1.505(7) . ?
C008 C035 1.535(6) . ?
C008 C013 1.550(6) . ?
C009 C011 1.400(6) . ?
C009 C027 1.413(7) . ?
C009 C024 1.435(7) . ?
C010 C024 1.365(6) . ?
C010 C035 1.498(7) . ?
C011 C020 1.379(7) . ?
C2 C033 1.340(7) . ?
C2 C021 1.503(6) . ?
C013 C015 1.496(6) . ?
C013 C014 1.545(6) . ?
C014 C019 1.503(7) . ?
C014 C024 1.507(7) . ?
C015 C018 1.368(6) . ?
C016 C022 1.391(7) . ?
C017 C023 1.368(7) . ?
C020 C030 1.398(7) . ?
C022 C031 1.376(7) . ?
C023 C031 1.401(7) . ?
C025 C1 1.501(6) . ?
C027 C032 1.387(7) . ?
C1 C034 1.280(7) . ?
C030 C032 1.376(7) . ?

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
C029 O002 C036 116.1(4) . . ?
C019 O004 C026 116.4(4) . . ?
C010 N005 C027 108.5(4) . . ?
C010 N005 C021 125.6(4) . . ?
C027 N005 C021 125.8(4) . . ?
C016 N006 C015 108.7(4) . . ?
C016 N006 C025 123.3(4) . . ?
C015 N006 C025 127.9(4) . . ?
C016 C007 C017 118.6(5) . . ?
C016 C007 C018 106.7(4) . . ?
C017 C007 C018 134.6(5) . . ?
C029 C008 C035 107.3(4) . . ?
C029 C008 C013 114.2(4) . . ?
C035 C008 C013 110.3(4) . . ?
C011 C009 C027 117.9(4) . . ?
C011 C009 C024 135.5(5) . . ?
C027 C009 C024 106.7(4) . . ?
C024 C010 N005 110.5(4) . . ?
C024 C010 C035 126.2(4) . . ?
N005 C010 C035 123.3(4) . . ?
C020 C011 C009 119.6(5) . . ?
C033 C2 C021 124.2(5) . . ?
C015 C013 C014 111.0(4) . . ?
C015 C013 C008 115.1(4) . . ?
C014 C013 C008 107.1(4) . . ?
C019 C014 C024 109.3(4) . . ?
C019 C014 C013 111.0(4) . . ?
C024 C014 C013 109.0(4) . . ?
C018 C015 N006 108.4(4) . . ?
C018 C015 C013 128.7(5) . . ?
N006 C015 C013 122.4(4) . . ?
N006 C016 C022 129.4(5) . . ?
N006 C016 C007 107.9(4) . . ?
C022 C016 C007 122.7(5) . . ?
C023 C017 C007 118.6(5) . . ?
C015 C018 C007 108.3(4) . . ?
O001 C019 O004 124.0(5) . . ?
O001 C019 C014 125.6(5) . . ?
O004 C019 C014 110.3(4) . . ?
C011 C020 C030 121.0(5) . . ?
N005 C021 C2 113.6(4) . . ?
C031 C022 C016 117.2(5) . . ?
C017 C023 C031 121.8(5) . . ?
C010 C024 C009 106.5(4) . . ?
C010 C024 C014 120.9(4) . . ?
C009 C024 C014 132.5(4) . . ?
N006 C025 C1 113.0(4) . . ?
N005 C027 C032 129.4(5) . . ?
N005 C027 C009 107.9(4) . . ?
C032 C027 C009 122.7(5) . . ?
C034 C1 C025 121.7(5) . . ?
O003 C029 O002 124.7(5) . . ?
O003 C029 C008 125.2(5) . . ?
O002 C029 C008 110.0(4) . . ?
C032 C030 C020 121.0(5) . . ?
C022 C031 C023 121.1(5) . . ?
C030 C032 C027 117.8(5) . . ?
C010 C035 C008 110.0(4) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        28.34
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.563
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.102
####################################################################### 
# 
# 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_8feba_0m
_database_code_depnum_ccdc_archive 'CCDC 1562219'
_audit_update_record             
;
2017-07-14 deposited with the CCDC.
2018-03-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C60 H60 N4 O8'
_chemical_formula_sum            'C60 H60 N4 O8'
_chemical_formula_weight         965.12

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   13.1542(9)
_cell_length_b                   13.3153(9)
_cell_length_c                   15.7230(11)
_cell_angle_alpha                103.217(2)
_cell_angle_beta                 113.154(2)
_cell_angle_gamma                93.739(2)
_cell_volume                     2427.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8984
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      25.5

_exptl_crystal_description       PRISM
_exptl_crystal_colour            YELLOW
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      1.32
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            30641
_diffrn_reflns_av_R_equivalents  0.0822
_diffrn_reflns_av_sigmaI/netI    0.1028
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         25.50
_reflns_number_total             8984
_reflns_number_gt                5196
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART APEX'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT PLUS'
_computing_structure_solution    'SIR97(Altomare, et. al. 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'WingX publication routine (Farrugia, 1999)'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0614P)²+2.3289P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0015(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         8984
_refine_ls_number_parameters     678
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1321
_refine_ls_R_factor_gt           0.0642
_refine_ls_wR_factor_ref         0.1640
_refine_ls_wR_factor_gt          0.1341
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_restrained_S_all      0.976
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C65 C 0.6161(4) -0.0361(5) -0.0384(3) 0.0570(14) Uani 1 1 d . . .
C66 C 1.3924(3) -0.0162(3) 0.2657(3) 0.0345(9) Uani 1 1 d . . .
H66A H 1.3529 -0.0307 0.1971 0.052 Uiso 1 1 calc R . .
H66B H 1.4152 -0.0789 0.2818 0.052 Uiso 1 1 calc R . .
H66C H 1.4574 0.0367 0.2885 0.052 Uiso 1 1 calc R . .
H101 H 0.256(3) 0.231(2) -0.072(2) 0.029(9) Uiso 1 1 d . . .
H102 H 0.129(3) 0.202(3) -0.160(2) 0.035(10) Uiso 1 1 d . . .
H103 H 0.724(3) 0.637(3) 0.415(2) 0.033(10) Uiso 1 1 d . . .
H104 H 0.861(3) 0.677(3) 0.490(2) 0.041(10) Uiso 1 1 d . . .
H105 H 0.645(8) 0.036(8) -0.007(7) 0.28(5) Uiso 1 1 d . . .
H115 H 0.540(3) -0.091(3) -0.058(3) 0.065(13) Uiso 1 1 d . . .
O6 O 0.76884(16) -0.00828(16) 0.24055(15) 0.0223(5) Uani 1 1 d . . .
O8 O 1.31895(17) 0.02077(17) 0.31068(16) 0.0271(6) Uani 1 1 d . . .
N4 N 0.9098(2) -0.01255(19) 0.06529(17) 0.0176(6) Uani 1 1 d . . .
N3 N 1.0941(2) 0.09542(19) 0.47977(17) 0.0169(6) Uani 1 1 d . . .
O5 O 0.67538(18) 0.11534(18) 0.18890(18) 0.0384(7) Uani 1 1 d . . .
O7 O 1.3129(2) 0.15723(19) 0.24914(17) 0.0365(6) Uani 1 1 d . . .
C42 C 0.9544(2) 0.0486(2) 0.1600(2) 0.0155(7) Uani 1 1 d . . .
C45 C 1.1170(2) -0.1627(2) 0.1681(2) 0.0187(7) Uani 1 1 d . . .
H45 H 1.1700 -0.1595 0.2293 0.022 Uiso 1 1 calc R . .
C50 C 0.7624(3) 0.0876(2) 0.2289(2) 0.0201(7) Uani 1 1 d . . .
C41 C 1.0372(2) 0.0052(2) 0.2166(2) 0.0148(7) Uani 1 1 d . . .
C37 C 1.0495(2) 0.0924(2) 0.3821(2) 0.0150(7) Uani 1 1 d . . .
C44 C 1.0475(2) -0.0872(2) 0.1546(2) 0.0167(7) Uani 1 1 d . . .
C49 C 0.9669(2) -0.0961(2) 0.0603(2) 0.0162(7) Uani 1 1 d . . .
C52 C 0.8130(2) -0.0007(2) -0.0167(2) 0.0206(7) Uani 1 1 d . . .
H52A H 0.8265 -0.0214 -0.0741 0.025 Uiso 1 1 calc R . .
H52B H 0.8056 0.0726 -0.0059 0.025 Uiso 1 1 calc R . .
C59 C 1.2830(3) 0.1086(3) 0.2933(2) 0.0247(8) Uani 1 1 d . . .
C36 C 0.9451(2) 0.1780(2) 0.4500(2) 0.0171(7) Uani 1 1 d . . .
C55 C 1.1836(2) 0.0428(2) 0.5297(2) 0.0193(7) Uani 1 1 d . . .
H55A H 1.1771 -0.0245 0.4863 0.023 Uiso 1 1 calc R . .
H55B H 1.1729 0.0297 0.5841 0.023 Uiso 1 1 calc R . .
C58 C 1.2050(2) 0.1398(2) 0.3387(2) 0.0202(7) Uani 1 1 d . . .
H58A H 1.1697 0.1950 0.3140 0.024 Uiso 1 1 calc R . .
H58B H 1.2490 0.1689 0.4075 0.024 Uiso 1 1 calc R . .
C48 C 0.9564(3) -0.1751(2) -0.0192(2) 0.0202(7) Uani 1 1 d . . .
H48 H 0.9037 -0.1791 -0.0808 0.024 Uiso 1 1 calc R . .
C46 C 1.1060(3) -0.2416(2) 0.0899(2) 0.0218(8) Uani 1 1 d . . .
H46 H 1.1517 -0.2922 0.0988 0.026 Uiso 1 1 calc R . .
C43 C 0.9180(2) 0.1498(2) 0.1897(2) 0.0186(7) Uani 1 1 d . . .
H43A H 0.8582 0.1602 0.1336 0.022 Uiso 1 1 calc R . .
H43B H 0.9806 0.2063 0.2117 0.022 Uiso 1 1 calc R . .
C47 C 1.0271(3) -0.2472(2) -0.0029(2) 0.0231(8) Uani 1 1 d . . .
H47 H 1.0224 -0.3007 -0.0547 0.028 Uiso 1 1 calc R . .
C38 C 0.9584(2) 0.1418(2) 0.3620(2) 0.0175(7) Uani 1 1 d . . .
C39 C 0.8765(2) 0.1574(2) 0.2697(2) 0.0172(7) Uani 1 1 d . . .
H39 H 0.8631 0.2294 0.2860 0.021 Uiso 1 1 calc R . .
C40 C 1.1111(2) 0.0507(2) 0.3225(2) 0.0160(7) Uani 1 1 d . . .
H40 H 1.1475 -0.0052 0.3467 0.019 Uiso 1 1 calc R . .
C34 C 1.0309(2) 0.1471(2) 0.5215(2) 0.0158(7) Uani 1 1 d . . .
C32 C 0.9660(3) 0.2247(2) 0.6377(2) 0.0238(8) Uani 1 1 d . . .
H32 H 0.9715 0.2406 0.7003 0.029 Uiso 1 1 calc R . .
C33 C 1.0414(3) 0.1690(2) 0.6157(2) 0.0200(7) Uani 1 1 d . . .
H33 H 1.0973 0.1469 0.6622 0.024 Uiso 1 1 calc R . .
C31 C 0.8814(3) 0.2579(2) 0.5680(2) 0.0231(8) Uani 1 1 d . . .
H31 H 0.8324 0.2962 0.5852 0.028 Uiso 1 1 calc R . .
C35 C 0.8696(3) 0.2345(2) 0.4743(2) 0.0203(7) Uani 1 1 d . . .
H35 H 0.8126 0.2559 0.4280 0.024 Uiso 1 1 calc R . .
C51 C 0.6622(3) -0.0776(3) 0.2022(2) 0.0293(8) Uani 1 1 d . . .
H51A H 0.6175 -0.0486 0.2342 0.044 Uiso 1 1 calc R . .
H51B H 0.6748 -0.1449 0.2125 0.044 Uiso 1 1 calc R . .
H51C H 0.6235 -0.0852 0.1344 0.044 Uiso 1 1 calc R . .
C56 C 1.2977(3) 0.1016(3) 0.5647(3) 0.0418(11) Uani 1 1 d . . .
H56 H 1.3144 0.1711 0.6010 0.050 Uiso 1 1 calc R . .
C57 C 1.3780(3) 0.0578(5) 0.5457(3) 0.0761(18) Uani 1 1 d . . .
H57A H 1.3624 -0.0117 0.5094 0.091 Uiso 1 1 calc R . .
H57B H 1.4493 0.0968 0.5688 0.091 Uiso 1 1 calc R . .
C54 C 0.7058(3) -0.0637(4) -0.0337(3) 0.0444(11) Uani 1 1 d . . .
H54 H 0.7063 -0.1351 -0.0421 0.053 Uiso 1 1 calc R . .
N2 N 0.39517(19) 0.40845(18) 0.01643(17) 0.0149(6) Uani 1 1 d . . .
O4 O 0.80771(17) 0.39920(17) 0.32873(15) 0.0272(6) Uani 1 1 d . . .
O3 O 0.73349(18) 0.51143(18) 0.24546(16) 0.0304(6) Uani 1 1 d . . .
N1 N 0.57126(19) 0.52320(19) 0.43118(17) 0.0180(6) Uani 1 1 d . . .
O2 O 0.14868(18) 0.49207(17) 0.14813(17) 0.0298(6) Uani 1 1 d . . .
O1 O 0.16413(19) 0.38737(19) 0.24394(16) 0.0336(6) Uani 1 1 d . . .
C19 C 0.3648(2) 0.6708(2) 0.3223(2) 0.0191(7) Uani 1 1 d . . .
H19 H 0.3121 0.6663 0.2606 0.023 Uiso 1 1 calc R . .
C29 C 0.7217(3) 0.4323(3) 0.2675(2) 0.0197(7) Uani 1 1 d . . .
C15 C 0.5147(2) 0.6066(2) 0.4332(2) 0.0176(7) Uani 1 1 d . . .
C6 C 0.5482(2) 0.3323(2) 0.0505(2) 0.0163(7) Uani 1 1 d . . .
C13 C 0.4486(2) 0.5034(2) 0.2784(2) 0.0159(7) Uani 1 1 d . . .
C8 C 0.4375(2) 0.4127(2) 0.1139(2) 0.0146(7) Uani 1 1 d . . .
C5 C 0.4632(2) 0.3610(2) -0.0223(2) 0.0150(7) Uani 1 1 d . . .
C9 C 0.3764(2) 0.4585(2) 0.1723(2) 0.0157(7) Uani 1 1 d . . .
H9 H 0.3449 0.5163 0.1480 0.019 Uiso 1 1 calc R . .
C21 C 0.1926(2) 0.4173(2) 0.1889(2) 0.0204(7) Uani 1 1 d . . .
C20 C 0.2758(2) 0.3756(2) 0.1531(2) 0.0187(7) Uani 1 1 d . . .
H20A H 0.2370 0.3431 0.0843 0.022 Uiso 1 1 calc R . .
H20B H 0.3046 0.3214 0.1833 0.022 Uiso 1 1 calc R . .
C23 C 0.6687(2) 0.5158(2) 0.5149(2) 0.0211(7) Uani 1 1 d . . .
H23A H 0.6775 0.4430 0.5074 0.025 Uiso 1 1 calc R . .
H23B H 0.6550 0.5393 0.5719 0.025 Uiso 1 1 calc R . .
C7 C 0.5314(2) 0.3664(2) 0.1369(2) 0.0152(7) Uani 1 1 d . . .
C2 C 0.6217(3) 0.2615(2) -0.0631(2) 0.0218(8) Uani 1 1 d . . .
H2 H 0.6742 0.2270 -0.0782 0.026 Uiso 1 1 calc R . .
C16 C 0.5244(3) 0.6875(2) 0.5114(2) 0.0206(7) Uani 1 1 d . . .
H16 H 0.5773 0.6933 0.5734 0.025 Uiso 1 1 calc R . .
C10 C 0.6134(2) 0.3558(2) 0.2311(2) 0.0188(7) Uani 1 1 d . . .
H10 H 0.6325 0.2857 0.2174 0.023 Uiso 1 1 calc R . .
C12 C 0.5309(2) 0.4616(2) 0.3368(2) 0.0156(7) Uani 1 1 d . . .
C14 C 0.4360(2) 0.5966(2) 0.3380(2) 0.0161(7) Uani 1 1 d . . .
C24 C 0.7750(3) 0.5789(2) 0.5294(2) 0.0220(8) Uani 1 1 d . . .
H24 H 0.8394 0.5788 0.5829 0.026 Uiso 1 1 calc R . .
C27 C 0.2015(2) 0.3578(3) -0.1093(2) 0.0204(7) Uani 1 1 d . . .
H27 H 0.1400 0.3763 -0.1540 0.025 Uiso 1 1 calc R . .
C18 C 0.3739(3) 0.7504(2) 0.3995(2) 0.0229(8) Uani 1 1 d . . .
H18 H 0.3269 0.7999 0.3893 0.027 Uiso 1 1 calc R . .
C3 C 0.5371(3) 0.2932(2) -0.1343(2) 0.0223(8) Uani 1 1 d . . .
H3 H 0.5350 0.2800 -0.1957 0.027 Uiso 1 1 calc R . .
C28 C 0.1962(3) 0.2582(3) -0.1130(3) 0.0248(8) Uani 1 1 d . . .
C26 C 0.2957(2) 0.4447(2) -0.0410(2) 0.0191(7) Uani 1 1 d . . .
H26A H 0.3155 0.4863 -0.0772 0.023 Uiso 1 1 calc R . .
H26B H 0.2704 0.4897 0.0018 0.023 Uiso 1 1 calc R . .
C17 C 0.4523(3) 0.7586(3) 0.4931(2) 0.0257(8) Uani 1 1 d . . .
H17 H 0.4559 0.8129 0.5439 0.031 Uiso 1 1 calc R . .
C4 C 0.4572(2) 0.3433(2) -0.1154(2) 0.0199(7) Uani 1 1 d . . .
H4 H 0.4014 0.3645 -0.1626 0.024 Uiso 1 1 calc R . .
C1 C 0.6281(3) 0.2807(2) 0.0292(2) 0.0209(7) Uani 1 1 d . . .
H1 H 0.6845 0.2598 0.0762 0.025 Uiso 1 1 calc R . .
C11 C 0.5704(3) 0.3614(2) 0.3094(2) 0.0196(7) Uani 1 1 d . . .
H11A H 0.5090 0.3036 0.2869 0.023 Uiso 1 1 calc R . .
H11B H 0.6302 0.3525 0.3663 0.023 Uiso 1 1 calc R . .
C30 C 0.9172(3) 0.4612(3) 0.3624(3) 0.0382(10) Uani 1 1 d . . .
H30A H 0.9376 0.4559 0.3095 0.057 Uiso 1 1 calc R . .
H30B H 0.9714 0.4358 0.4107 0.057 Uiso 1 1 calc R . .
H30C H 0.9155 0.5331 0.3894 0.057 Uiso 1 1 calc R . .
C25 C 0.7861(3) 0.6344(3) 0.4740(3) 0.0275(8) Uani 1 1 d . . .
C22 C 0.0650(3) 0.5349(3) 0.1763(3) 0.0463(11) Uani 1 1 d . . .
H22A H 0.0025 0.4804 0.1572 0.069 Uiso 1 1 calc R . .
H22B H 0.0399 0.5888 0.1456 0.069 Uiso 1 1 calc R . .
H22C H 0.0971 0.5641 0.2449 0.069 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
C65 C54 1.238(5) . ?
C66 O8 1.454(4) . ?
O6 C50 1.334(4) . ?
O6 C51 1.447(3) . ?
O8 C59 1.335(4) . ?
N4 C42 1.386(4) . ?
N4 C49 1.387(4) . ?
N4 C52 1.462(4) . ?
N3 C34 1.376(4) . ?
N3 C37 1.402(4) . ?
N3 C55 1.457(4) . ?
O5 C50 1.199(3) . ?
O7 C59 1.201(4) . ?
C42 C41 1.366(4) . ?
C42 C43 1.495(4) . ?
C45 C46 1.373(4) . ?
C45 C44 1.399(4) . ?
C50 C39 1.522(4) . ?
C41 C44 1.436(4) . ?
C41 C40 1.508(4) . ?
C37 C38 1.367(4) . ?
C37 C40 1.503(4) . ?
C44 C49 1.416(4) . ?
C49 C48 1.389(4) . ?
C52 C54 1.486(4) . ?
C59 C58 1.494(4) . ?
C36 C35 1.401(4) . ?
C36 C34 1.407(4) . ?
C36 C38 1.440(4) . ?
C55 C56 1.472(4) . ?
C58 C40 1.557(4) . ?
C48 C47 1.376(4) . ?
C46 C47 1.401(4) . ?
C43 C39 1.543(4) . ?
C38 C39 1.498(4) . ?
C34 C33 1.391(4) . ?
C32 C33 1.379(4) . ?
C32 C31 1.401(4) . ?
C31 C35 1.377(4) . ?
C56 C57 1.340(6) . ?
N2 C5 1.377(4) . ?
N2 C8 1.396(4) . ?
N2 C26 1.454(3) . ?
O4 C29 1.343(3) . ?
O4 C30 1.443(4) . ?
O3 C29 1.201(4) . ?
N1 C15 1.379(4) . ?
N1 C12 1.387(4) . ?
N1 C23 1.460(4) . ?
O2 C21 1.346(4) . ?
O2 C22 1.443(4) . ?
O1 C21 1.201(4) . ?
C19 C18 1.375(4) . ?
C19 C14 1.403(4) . ?
C29 C10 1.516(4) . ?
C15 C16 1.393(4) . ?
C15 C14 1.414(4) . ?
C6 C1 1.398(4) . ?
C6 C5 1.399(4) . ?
C6 C7 1.438(4) . ?
C13 C12 1.362(4) . ?
C13 C14 1.436(4) . ?
C13 C9 1.506(4) . ?
C8 C7 1.373(4) . ?
C8 C9 1.500(4) . ?
C5 C4 1.397(4) . ?
C9 C20 1.550(4) . ?
C21 C20 1.497(4) . ?
C23 C24 1.490(4) . ?
C7 C10 1.496(4) . ?
C2 C1 1.382(4) . ?
C2 C3 1.403(4) . ?
C16 C17 1.380(4) . ?
C10 C11 1.533(4) . ?
C12 C11 1.496(4) . ?
C24 C25 1.307(4) . ?
C27 C28 1.310(4) . ?
C27 C26 1.492(4) . ?
C18 C17 1.400(4) . ?
C3 C4 1.372(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
C50 O6 C51 115.2(2) . . ?
C59 O8 C66 114.2(3) . . ?
C42 N4 C49 108.5(2) . . ?
C42 N4 C52 128.0(2) . . ?
C49 N4 C52 123.3(3) . . ?
C34 N3 C37 109.0(2) . . ?
C34 N3 C55 123.3(2) . . ?
C37 N3 C55 127.3(2) . . ?
C41 C42 N4 110.0(3) . . ?
C41 C42 C43 127.4(3) . . ?
N4 C42 C43 122.5(2) . . ?
C46 C45 C44 119.3(3) . . ?
O5 C50 O6 123.3(3) . . ?
O5 C50 C39 123.4(3) . . ?
O6 C50 C39 113.3(2) . . ?
C42 C41 C44 107.0(3) . . ?
C42 C41 C40 126.6(3) . . ?
C44 C41 C40 126.2(3) . . ?
C38 C37 N3 108.8(3) . . ?
C38 C37 C40 131.4(3) . . ?
N3 C37 C40 119.4(2) . . ?
C45 C44 C49 118.3(3) . . ?
C45 C44 C41 134.7(3) . . ?
C49 C44 C41 107.0(3) . . ?
N4 C49 C48 129.8(3) . . ?
N4 C49 C44 107.5(3) . . ?
C48 C49 C44 122.6(3) . . ?
N4 C52 C54 113.5(3) . . ?
O7 C59 O8 123.7(3) . . ?
O7 C59 C58 124.9(3) . . ?
O8 C59 C58 111.3(3) . . ?
C35 C36 C34 119.5(3) . . ?
C35 C36 C38 133.6(3) . . ?
C34 C36 C38 106.9(3) . . ?
N3 C55 C56 114.5(3) . . ?
C59 C58 C40 115.7(3) . . ?
C47 C48 C49 117.3(3) . . ?
C45 C46 C47 121.2(3) . . ?
C42 C43 C39 115.0(2) . . ?
C48 C47 C46 121.4(3) . . ?
C37 C38 C36 107.5(3) . . ?
C37 C38 C39 131.8(3) . . ?
C36 C38 C39 120.7(3) . . ?
C38 C39 C50 113.4(2) . . ?
C38 C39 C43 115.8(2) . . ?
C50 C39 C43 109.4(2) . . ?
C37 C40 C41 114.4(2) . . ?
C37 C40 C58 108.6(2) . . ?
C41 C40 C58 110.6(2) . . ?
N3 C34 C33 130.3(3) . . ?
N3 C34 C36 107.9(3) . . ?
C33 C34 C36 121.8(3) . . ?
C33 C32 C31 121.6(3) . . ?
C32 C33 C34 117.6(3) . . ?
C35 C31 C32 120.9(3) . . ?
C31 C35 C36 118.7(3) . . ?
C57 C56 C55 121.9(4) . . ?
C65 C54 C52 130.2(5) . . ?
C5 N2 C8 109.1(2) . . ?
C5 N2 C26 122.2(2) . . ?
C8 N2 C26 128.7(2) . . ?
C29 O4 C30 115.9(3) . . ?
C15 N1 C12 108.6(2) . . ?
C15 N1 C23 122.6(3) . . ?
C12 N1 C23 128.1(2) . . ?
C21 O2 C22 114.9(3) . . ?
C18 C19 C14 119.1(3) . . ?
O3 C29 O4 122.5(3) . . ?
O3 C29 C10 126.8(3) . . ?
O4 C29 C10 110.6(3) . . ?
N1 C15 C16 129.4(3) . . ?
N1 C15 C14 107.9(3) . . ?
C16 C15 C14 122.6(3) . . ?
C1 C6 C5 119.2(3) . . ?
C1 C6 C7 133.5(3) . . ?
C5 C6 C7 107.3(3) . . ?
C12 C13 C14 107.4(3) . . ?
C12 C13 C9 127.6(3) . . ?
C14 C13 C9 124.8(3) . . ?
C7 C8 N2 108.6(2) . . ?
C7 C8 C9 131.7(3) . . ?
N2 C8 C9 119.6(2) . . ?
N2 C5 C4 129.8(3) . . ?
N2 C5 C6 107.8(3) . . ?
C4 C5 C6 122.3(3) . . ?
C8 C9 C13 115.0(2) . . ?
C8 C9 C20 109.2(2) . . ?
C13 C9 C20 111.6(2) . . ?
O1 C21 O2 122.9(3) . . ?
O1 C21 C20 126.0(3) . . ?
O2 C21 C20 111.0(3) . . ?
C21 C20 C9 114.9(3) . . ?
N1 C23 C24 113.4(3) . . ?
C8 C7 C6 107.2(3) . . ?
C8 C7 C10 131.4(3) . . ?
C6 C7 C10 121.3(3) . . ?
C1 C2 C3 120.9(3) . . ?
C17 C16 C15 117.2(3) . . ?
C7 C10 C29 110.2(2) . . ?
C7 C10 C11 116.2(2) . . ?
C29 C10 C11 111.5(3) . . ?
C13 C12 N1 109.6(3) . . ?
C13 C12 C11 127.6(3) . . ?
N1 C12 C11 122.7(3) . . ?
C19 C14 C15 118.4(3) . . ?
C19 C14 C13 135.1(3) . . ?
C15 C14 C13 106.5(3) . . ?
C25 C24 C23 126.0(3) . . ?
C28 C27 C26 126.8(3) . . ?
C19 C18 C17 121.4(3) . . ?
C4 C3 C2 121.5(3) . . ?
N2 C26 C27 113.4(2) . . ?
C16 C17 C18 121.2(3) . . ?
C3 C4 C5 117.3(3) . . ?
C2 C1 C6 118.8(3) . . ?
C12 C11 C10 114.3(2) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.662
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.060
####################################################################### 
# 
# 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_12decc_0m
_database_code_depnum_ccdc_archive 'CCDC 1562220'
_audit_update_record             
;
2017-08-29 deposited with the CCDC.
2018-03-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H26 N2 O4'
_chemical_formula_sum            'C26 H26 N2 O4'
_chemical_formula_weight         430.49

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   p-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.581(5)
_cell_length_b                   10.819(5)
_cell_length_c                   13.144(5)
_cell_angle_alpha                89.938(5)
_cell_angle_beta                 87.155(5)
_cell_angle_gamma                82.887(5)
_cell_volume                     1068.4(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3789
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      25.1

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      1.34
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   SADABS


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13025
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0361
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         25.10
_reflns_number_total             3789
_reflns_number_gt                2964
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART APEX'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT PLUS'
_computing_structure_solution    'SIR97(Altomare, et. al. 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'WingX publication routine (Farrugia, 1999)'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0612P)²+0.7673P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3789
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1352
_refine_ls_wR_factor_gt          0.1261
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.3071(2) 0.17682(15) 0.49653(12) 0.0379(4) Uani 1 1 d . . .
N1 N 0.2726(2) 0.47161(16) 0.05670(13) 0.0230(4) Uani 1 1 d . . .
O003 O -0.1846(2) 0.23427(15) 0.50170(12) 0.0375(4) Uani 1 1 d . . .
O004 O 0.2404(2) 0.11242(15) 0.34301(12) 0.0375(4) Uani 1 1 d . . .
O1 O -0.3513(2) 0.39164(15) 0.58488(12) 0.0339(4) Uani 1 1 d . . .
N006 N 0.6080(2) 0.11427(16) -0.05383(13) 0.0240(4) Uani 1 1 d . . .
C007 C 0.1582(3) 0.5369(2) 0.12892(16) 0.0224(5) Uani 1 1 d . . .
C008 C 0.5378(3) 0.22438(18) 0.20261(15) 0.0212(5) Uani 1 1 d . . .
C009 C 0.2494(3) 0.33870(19) 0.07010(15) 0.0213(5) Uani 1 1 d . . .
H009 H 0.1422 0.3217 0.0367 0.026 Uiso 1 1 calc R . .
C010 C 0.0913(3) 0.6620(2) 0.13001(17) 0.0254(5) Uani 1 1 d . . .
H010 H 0.1246 0.7153 0.0789 0.031 Uiso 1 1 calc R . .
C011 C 0.3928(3) 0.32148(19) 0.24664(15) 0.0210(5) Uani 1 1 d . . .
H011 H 0.4382 0.4018 0.2368 0.025 Uiso 1 1 calc R . .
C012 C 0.5322(3) 0.20012(18) 0.09883(15) 0.0206(5) Uani 1 1 d . . .
C013 C 0.6594(3) 0.11639(18) 0.04541(15) 0.0219(5) Uani 1 1 d . . .
C014 C -0.0144(3) 0.49988(19) 0.28444(16) 0.0227(5) Uani 1 1 d . . .
C015 C 0.4034(3) 0.25007(19) 0.03060(15) 0.0215(5) Uani 1 1 d . . .
C016 C 0.2969(3) 0.1880(2) 0.39560(16) 0.0274(5) Uani 1 1 d . . .
C017 C -0.0766(3) 0.4132(2) 0.35958(16) 0.0234(5) Uani 1 1 d . . .
H017 H -0.0326 0.3296 0.3505 0.028 Uiso 1 1 calc R . .
C018 C 0.6791(3) 0.16295(19) 0.25201(16) 0.0251(5) Uani 1 1 d . . .
H018 H 0.6889 0.1763 0.3213 0.030 Uiso 1 1 calc R . .
C019 C 0.8012(3) 0.0535(2) 0.09586(17) 0.0264(5) Uani 1 1 d . . .
H019 H 0.8865 -0.0034 0.0623 0.032 Uiso 1 1 calc R . .
C020 C 0.4535(3) 0.19533(19) -0.06186(16) 0.0232(5) Uani 1 1 d . . .
H020 H 0.3928 0.2104 -0.1212 0.028 Uiso 1 1 calc R . .
C021 C -0.0810(3) 0.6280(2) 0.28513(17) 0.0263(5) Uani 1 1 d . . .
H021 H -0.1619 0.6599 0.3369 0.032 Uiso 1 1 calc R . .
C022 C -0.2375(3) 0.3433(2) 0.50951(16) 0.0256(5) Uani 1 1 d . . .
C023 C 0.1098(3) 0.45693(19) 0.20687(16) 0.0216(5) Uani 1 1 d . . .
C024 C 0.2856(3) 0.5171(2) -0.04702(16) 0.0266(5) Uani 1 1 d . . .
H02A H 0.1757 0.5118 -0.0790 0.040 Uiso 1 1 calc R . .
H02B H 0.3808 0.4674 -0.0845 0.040 Uiso 1 1 calc R . .
H02C H 0.3091 0.6023 -0.0461 0.040 Uiso 1 1 calc R . .
C025 C 0.2167(3) 0.33041(19) 0.18714(15) 0.0206(5) Uani 1 1 d . . .
H025 H 0.1469 0.2626 0.2057 0.025 Uiso 1 1 calc R . .
C026 C 0.3597(3) 0.3086(2) 0.36068(16) 0.0244(5) Uani 1 1 d . . .
H108 H 0.4692 0.3179 0.3935 0.029 Uiso 1 1 calc R . .
H109 H 0.2716 0.3767 0.3841 0.029 Uiso 1 1 calc R . .
C027 C 0.7019(3) 0.0432(2) -0.13746(17) 0.0288(5) Uani 1 1 d . . .
H02D H 0.7899 0.0900 -0.1684 0.043 Uiso 1 1 calc R . .
H02E H 0.6191 0.0268 -0.1871 0.043 Uiso 1 1 calc R . .
H02F H 0.7592 -0.0341 -0.1123 0.043 Uiso 1 1 calc R . .
C028 C 0.8085(3) 0.0801(2) 0.19817(17) 0.0280(5) Uani 1 1 d . . .
H028 H 0.9036 0.0415 0.2332 0.034 Uiso 1 1 calc R . .
C029 C -0.0275(3) 0.7055(2) 0.21013(18) 0.0284(5) Uani 1 1 d . . .
H029 H -0.0718 0.7896 0.2128 0.034 Uiso 1 1 calc R . .
C030 C -0.1889(3) 0.4407(2) 0.43942(16) 0.0264(5) Uani 1 1 d . . .
H030 H -0.2376 0.5229 0.4511 0.032 Uiso 1 1 calc R . .
C031 C -0.4020(3) 0.3046(3) 0.66044(18) 0.0395(6) Uani 1 1 d . . .
H03A H -0.4584 0.2413 0.6284 0.059 Uiso 1 1 calc R . .
H03B H -0.4834 0.3477 0.7106 0.059 Uiso 1 1 calc R . .
H03C H -0.2980 0.2669 0.6928 0.059 Uiso 1 1 calc R . .
C032 C 0.2385(4) 0.0685(2) 0.5406(2) 0.0491(7) Uani 1 1 d . . .
H03D H 0.1108 0.0801 0.5409 0.074 Uiso 1 1 calc R . .
H03E H 0.2754 0.0577 0.6092 0.074 Uiso 1 1 calc R . .
H03F H 0.2837 -0.0040 0.5009 0.074 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
O001 C016 1.337(3) . ?
O001 C032 1.448(3) . ?
N1 C007 1.386(3) . ?
N1 C024 1.452(3) . ?
N1 C009 1.479(3) . ?
O003 C022 1.201(3) . ?
O004 C016 1.203(3) . ?
O1 C022 1.343(3) . ?
O1 C031 1.439(3) . ?
N006 C013 1.381(3) . ?
N006 C020 1.382(3) . ?
N006 C027 1.447(3) . ?
C007 C010 1.385(3) . ?
C007 C023 1.404(3) . ?
C008 C018 1.379(3) . ?
C008 C012 1.393(3) . ?
C008 C011 1.516(3) . ?
C009 C015 1.488(3) . ?
C009 C025 1.550(3) . ?
C010 C029 1.394(3) . ?
C011 C026 1.517(3) . ?
C011 C025 1.574(3) . ?
C012 C013 1.401(3) . ?
C012 C015 1.416(3) . ?
C013 C019 1.395(3) . ?
C014 C023 1.393(3) . ?
C014 C021 1.415(3) . ?
C014 C017 1.462(3) . ?
C015 C020 1.368(3) . ?
C016 C026 1.507(3) . ?
C017 C030 1.328(3) . ?
C018 C028 1.408(3) . ?
C019 C028 1.381(3) . ?
C021 C029 1.372(3) . ?
C022 C030 1.468(3) . ?
C023 C025 1.517(3) . ?

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
C016 O001 C032 115.45(19) . . ?
C007 N1 C024 120.25(18) . . ?
C007 N1 C009 106.27(16) . . ?
C024 N1 C009 117.12(17) . . ?
C022 O1 C031 115.68(19) . . ?
C013 N006 C020 108.71(17) . . ?
C013 N006 C027 126.35(19) . . ?
C020 N006 C027 124.90(18) . . ?
C010 C007 N1 128.6(2) . . ?
C010 C007 C023 121.0(2) . . ?
N1 C007 C023 110.43(18) . . ?
C018 C008 C012 116.64(19) . . ?
C018 C008 C011 127.54(19) . . ?
C012 C008 C011 115.72(18) . . ?
N1 C009 C015 114.45(17) . . ?
N1 C009 C025 101.87(16) . . ?
C015 C009 C025 112.75(17) . . ?
C007 C010 C029 117.9(2) . . ?
C008 C011 C026 112.95(17) . . ?
C008 C011 C025 113.03(17) . . ?
C026 C011 C025 112.66(17) . . ?
C008 C012 C013 123.09(19) . . ?
C008 C012 C015 128.19(19) . . ?
C013 C012 C015 108.71(18) . . ?
N006 C013 C019 133.27(19) . . ?
N006 C013 C012 106.63(18) . . ?
C019 C013 C012 120.09(19) . . ?
C023 C014 C021 117.6(2) . . ?
C023 C014 C017 120.27(19) . . ?
C021 C014 C017 122.07(19) . . ?
C020 C015 C012 106.10(19) . . ?
C020 C015 C009 134.7(2) . . ?
C012 C015 C009 119.07(18) . . ?
O004 C016 O001 123.4(2) . . ?
O004 C016 C026 126.5(2) . . ?
O001 C016 C026 110.11(18) . . ?
C030 C017 C014 127.2(2) . . ?
C008 C018 C028 120.4(2) . . ?
C028 C019 C013 116.6(2) . . ?
C015 C020 N006 109.84(19) . . ?
C029 C021 C014 120.6(2) . . ?
O003 C022 O1 123.5(2) . . ?
O003 C022 C030 125.4(2) . . ?
O1 C022 C030 111.13(19) . . ?
C014 C023 C007 120.79(19) . . ?
C014 C023 C025 131.69(19) . . ?
C007 C023 C025 107.51(18) . . ?
C023 C025 C009 99.33(16) . . ?
C023 C025 C011 109.28(16) . . ?
C009 C025 C011 113.18(16) . . ?
C016 C026 C011 115.79(17) . . ?
C019 C028 C018 123.2(2) . . ?
C021 C029 C010 122.0(2) . . ?
C017 C030 C022 121.1(2) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.731
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.054
