# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_LN307_0m
_database_code_depnum_ccdc_archive 'CCDC 1903900'
loop_
_audit_author_name
_audit_author_address
'Klaus Harms'
;University of Marburg
Germany
;
_audit_update_record             
;
2019-03-18 deposited with the CCDC.	2019-08-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C39 H32 N4 O5, 2(C H4 O)'
_chemical_formula_sum            'C41 H40 N4 O7'
_chemical_formula_weight         700.77

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.5439(5)
_cell_length_b                   12.3994(5)
_cell_length_c                   14.5971(6)
_cell_angle_alpha                87.794(2)
_cell_angle_beta                 79.277(2)
_cell_angle_gamma                68.813(2)
_cell_volume                     1747.47(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9945
_cell_measurement_theta_min      2.2982
_cell_measurement_theta_max      27.5144

_exptl_crystal_description       nugget
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_F_000             740
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_process_details   
; 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 QUEST area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 7.9
_diffrn_reflns_number            72214
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.298
_diffrn_reflns_theta_max         27.541
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8041
_reflns_number_gt                6839
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2015)'
_computing_cell_refinement       'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT V2014/1 (Bruker AXS Inc., 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact)'
_computing_publication_material  ?
_refine_special_details          
; 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0402P)²+1.3339P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0077(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         8041
_refine_ls_number_parameters     487
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1093
_refine_ls_wR_factor_gt          0.1042
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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_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 0.38525(11) 0.31980(11) 0.31102(7) 0.0243(3) Uani 1 1 d . . . . .
C1 C 0.51099(14) 0.28858(12) 0.29748(9) 0.0149(3) Uani 1 1 d . . . . .
C2 C 0.59827(14) 0.23261(12) 0.20180(9) 0.0147(3) Uani 1 1 d . . . . .
H2 H 0.652580 0.149927 0.212507 0.018 Uiso 1 1 calc R U . . .
C3 C 0.70284(14) 0.28876(12) 0.15476(9) 0.0137(3) Uani 1 1 d . . . . .
H3 H 0.654342 0.374676 0.159586 0.016 Uiso 1 1 calc R U . . .
C4 C 0.75554(14) 0.25370(12) 0.05152(9) 0.0139(3) Uani 1 1 d . . . . .
C5 C 0.81604(15) 0.13792(13) 0.02120(10) 0.0169(3) Uani 1 1 d . . . . .
H5 H 0.820120 0.078625 0.065010 0.020 Uiso 1 1 calc R U . . .
C6 C 0.87048(15) 0.10863(13) -0.07274(11) 0.0194(3) Uani 1 1 d . . . . .
H6 H 0.910252 0.029550 -0.092816 0.023 Uiso 1 1 calc R U . . .
C7 C 0.86693(15) 0.19468(14) -0.13743(10) 0.0203(3) Uani 1 1 d . . . . .
H7 H 0.905258 0.174668 -0.201433 0.024 Uiso 1 1 calc R U . . .
C8 C 0.80691(16) 0.30986(13) -0.10755(10) 0.0194(3) Uani 1 1 d . . . . .
H8 H 0.804469 0.369067 -0.151224 0.023 Uiso 1 1 calc R U . . .
C9 C 0.75015(15) 0.33915(13) -0.01370(10) 0.0165(3) Uani 1 1 d . . . . .
H9 H 0.707353 0.418332 0.005874 0.020 Uiso 1 1 calc R U . . .
N10 N 0.58400(13) 0.29398(11) 0.36270(8) 0.0163(2) Uani 1 1 d . . . . .
H10 H 0.675(2) 0.2727(16) 0.3465(13) 0.024(5) Uiso 1 1 d . . . . .
C11 C 0.53187(15) 0.33428(12) 0.45618(9) 0.0154(3) Uani 1 1 d . . . . .
C12 C 0.63439(15) 0.33878(12) 0.50618(10) 0.0157(3) Uani 1 1 d . . . . .
N13 N 0.76796(13) 0.30466(11) 0.45959(8) 0.0178(3) Uani 1 1 d . . . . .
C14 C 0.86145(16) 0.31005(14) 0.50562(11) 0.0221(3) Uani 1 1 d . . . . .
H14 H 0.954877 0.286228 0.473888 0.026 Uiso 1 1 calc R U . . .
C15 C 0.83111(18) 0.34920(14) 0.59948(11) 0.0251(3) Uani 1 1 d . . . . .
H15 H 0.902777 0.351134 0.629608 0.030 Uiso 1 1 calc R U . . .
C16 C 0.69775(18) 0.38421(14) 0.64642(11) 0.0233(3) Uani 1 1 d . . . . .
H16 H 0.675449 0.411651 0.709418 0.028 Uiso 1 1 calc R U . . .
C17 C 0.59285(16) 0.37936(12) 0.60062(10) 0.0181(3) Uani 1 1 d . . . . .
C18 C 0.45173(17) 0.41311(13) 0.64360(10) 0.0212(3) Uani 1 1 d . . . . .
H18 H 0.423154 0.439995 0.706877 0.025 Uiso 1 1 calc R U . . .
C19 C 0.35712(16) 0.40691(13) 0.59400(10) 0.0211(3) Uani 1 1 d . . . . .
H19 H 0.262749 0.429633 0.623554 0.025 Uiso 1 1 calc R U . . .
C20 C 0.39558(16) 0.36756(13) 0.49968(10) 0.0185(3) Uani 1 1 d . . . . .
H20 H 0.327595 0.364124 0.466524 0.022 Uiso 1 1 calc R U . . .
C21 C 0.82577(14) 0.25849(12) 0.20316(9) 0.0135(3) Uani 1 1 d . . . . .
C22 C 0.89545(14) 0.15571(12) 0.23837(9) 0.0149(3) Uani 1 1 d . . . . .
H22 H 0.872434 0.088335 0.238811 0.018 Uiso 1 1 calc R U . . .
N23 N 1.00620(12) 0.16373(10) 0.27391(8) 0.0141(2) Uani 1 1 d . . . . .
C24 C 1.00658(14) 0.27646(12) 0.26071(9) 0.0133(3) Uani 1 1 d . . . . .
C25 C 1.09412(14) 0.32880(12) 0.28289(10) 0.0154(3) Uani 1 1 d . . . . .
H25 H 1.169480 0.287738 0.312904 0.019 Uiso 1 1 calc R U . . .
C26 C 1.06669(15) 0.44338(13) 0.25932(10) 0.0172(3) Uani 1 1 d . . . . .
H26 H 1.124546 0.481385 0.273815 0.021 Uiso 1 1 calc R U . . .
C27 C 0.95647(15) 0.50461(12) 0.21487(10) 0.0174(3) Uani 1 1 d . . . . .
H27 H 0.940780 0.583072 0.199893 0.021 Uiso 1 1 calc R U . . .
C28 C 0.86979(14) 0.45235(12) 0.19238(9) 0.0155(3) Uani 1 1 d . . . . .
H28 H 0.795225 0.493876 0.161814 0.019 Uiso 1 1 calc R U . . .
C29 C 0.89472(14) 0.33703(12) 0.21574(9) 0.0134(3) Uani 1 1 d . . . . .
C30 C 1.08809(15) 0.07141(12) 0.32072(10) 0.0160(3) Uani 1 1 d . . . . .
O30 O 1.07688(12) -0.02174(9) 0.32330(8) 0.0219(2) Uani 1 1 d . . . . .
O31 O 1.17322(11) 0.10446(9) 0.35913(8) 0.0217(2) Uani 1 1 d . . . . .
C32 C 1.26777(17) 0.02391(14) 0.41691(13) 0.0274(4) Uani 1 1 d . . . . .
C33 C 1.36891(19) -0.07865(17) 0.35693(15) 0.0399(5) Uani 1 1 d . . . . .
H33A H 1.438316 -0.126446 0.392490 0.060 Uiso 1 1 calc R U . . .
H33B H 1.414906 -0.051320 0.301301 0.060 Uiso 1 1 calc R U . . .
H33C H 1.319171 -0.124754 0.338056 0.060 Uiso 1 1 calc R U . . .
C34 C 1.18382(19) -0.01038(16) 0.50050(12) 0.0315(4) Uani 1 1 d . . . . .
H34A H 1.244910 -0.053052 0.543172 0.047 Uiso 1 1 calc R U . . .
H34B H 1.139184 -0.059602 0.479767 0.047 Uiso 1 1 calc R U . . .
H34C H 1.112909 0.059273 0.532781 0.047 Uiso 1 1 calc R U . . .
C35 C 1.3363(2) 0.10160(19) 0.44791(19) 0.0511(6) Uani 1 1 d . . . . .
H35A H 1.392864 0.061905 0.493904 0.077 Uiso 1 1 calc R U . . .
H35B H 1.264897 0.173672 0.476005 0.077 Uiso 1 1 calc R U . . .
H35C H 1.395189 0.119284 0.393803 0.077 Uiso 1 1 calc R U . . .
N36 N 0.50172(12) 0.23312(10) 0.14247(8) 0.0146(2) Uani 1 1 d . . . . .
C37 C 0.46975(15) 0.13595(12) 0.12837(10) 0.0159(3) Uani 1 1 d . . . . .
O37 O 0.53030(11) 0.03875(9) 0.15204(8) 0.0232(2) Uani 1 1 d . . . . .
C38 C 0.34964(14) 0.17671(13) 0.08008(9) 0.0156(3) Uani 1 1 d . . . . .
C39 C 0.28036(16) 0.11446(14) 0.04812(11) 0.0216(3) Uani 1 1 d . . . . .
H39 H 0.308153 0.033000 0.054136 0.026 Uiso 1 1 calc R U . . .
C40 C 0.16761(17) 0.17695(15) 0.00660(11) 0.0246(3) Uani 1 1 d . . . . .
H40 H 0.117222 0.137363 -0.016332 0.030 Uiso 1 1 calc R U . . .
C41 C 0.12781(15) 0.29605(14) -0.00178(10) 0.0216(3) Uani 1 1 d . . . . .
H41 H 0.050099 0.336425 -0.029845 0.026 Uiso 1 1 calc R U . . .
C42 C 0.19934(15) 0.35765(13) 0.03007(10) 0.0178(3) Uani 1 1 d . . . . .
H42 H 0.172770 0.438996 0.023748 0.021 Uiso 1 1 calc R U . . .
C43 C 0.31041(14) 0.29521(12) 0.07116(9) 0.0145(3) Uani 1 1 d . . . . .
O1M O 0.54941(12) 0.60043(10) 0.11856(8) 0.0266(3) Uani 1 1 d . . . . .
H1M H 0.477(3) 0.578(2) 0.1086(17) 0.055(7) Uiso 1 1 d . . . . .
C2M C 0.49500(18) 0.72169(15) 0.13869(12) 0.0285(4) Uani 1 1 d . . . . .
H2M1 H 0.448502 0.762195 0.088340 0.043 Uiso 1 1 calc R U . . .
H2M2 H 0.570603 0.747997 0.143938 0.043 Uiso 1 1 calc R U . . .
H2M3 H 0.428406 0.738406 0.197652 0.043 Uiso 1 1 calc R U . . .
O3M O 0.7529(2) -0.04996(13) 0.24716(17) 0.0727(7) Uani 1 1 d . . . . .
H3M H 0.683(4) -0.034(3) 0.212(2) 0.094(11) Uiso 1 1 d . . . . .
C4M C 0.7892(2) -0.16099(18) 0.27845(16) 0.0425(5) Uani 1 1 d . . . . .
H4M1 H 0.819399 -0.215698 0.225088 0.064 Uiso 1 1 calc R U . . .
H4M2 H 0.709126 -0.170113 0.319551 0.064 Uiso 1 1 calc R U . . .
H4M3 H 0.864851 -0.176400 0.313036 0.064 Uiso 1 1 calc R U . . .
C44 C 0.40602(14) 0.33399(12) 0.11293(9) 0.0148(3) Uani 1 1 d . . . . .
O44 O 0.40705(11) 0.43005(9) 0.12077(7) 0.0202(2) 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
O1 C1 1.2182(18) . ?
C1 N10 1.3484(18) . ?
C1 C2 1.5538(19) . ?
C2 N36 1.4524(17) . ?
C2 C3 1.5519(19) . ?
C2 H2 1.0000 . ?
C3 C21 1.5127(18) . ?
C3 C4 1.5275(18) . ?
C3 H3 1.0000 . ?
C4 C9 1.390(2) . ?
C4 C5 1.395(2) . ?
C5 C6 1.392(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.392(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.386(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.394(2) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
N10 C11 1.4102(18) . ?
N10 H10 0.89(2) . ?
C11 C20 1.375(2) . ?
C11 C12 1.430(2) . ?
C12 N13 1.3638(19) . ?
C12 C17 1.4195(19) . ?
N13 C14 1.3135(19) . ?
C14 C15 1.411(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.363(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.414(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.416(2) . ?
C18 C19 1.362(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.414(2) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C22 1.357(2) . ?
C21 C29 1.4442(19) . ?
C22 N23 1.3985(18) . ?
C22 H22 0.9500 . ?
N23 C30 1.4027(18) . ?
N23 C24 1.4050(18) . ?
C24 C25 1.3922(19) . ?
C24 C29 1.4128(19) . ?
C25 C26 1.387(2) . ?
C25 H25 0.9500 . ?
C26 C27 1.397(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.385(2) . ?
C27 H27 0.9500 . ?
C28 C29 1.398(2) . ?
C28 H28 0.9500 . ?
C30 O30 1.2013(18) . ?
C30 O31 1.3263(18) . ?
O31 C32 1.4937(18) . ?
C32 C33 1.510(3) . ?
C32 C34 1.511(3) . ?
C32 C35 1.521(3) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
N36 C37 1.3950(18) . ?
N36 C44 1.4059(18) . ?
C37 O37 1.2137(18) . ?
C37 C38 1.483(2) . ?
C38 C39 1.382(2) . ?
C38 C43 1.383(2) . ?
C39 C40 1.395(2) . ?
C39 H39 0.9500 . ?
C40 C41 1.389(2) . ?
C40 H40 0.9500 . ?
C41 C42 1.394(2) . ?
C41 H41 0.9500 . ?
C42 C43 1.379(2) . ?
C42 H42 0.9500 . ?
C43 C44 1.4903(19) . ?
O1M C2M 1.423(2) . ?
O1M H1M 0.94(3) . ?
C2M H2M1 0.9800 . ?
C2M H2M2 0.9800 . ?
C2M H2M3 0.9800 . ?
O3M C4M 1.374(2) . ?
O3M H3M 0.93(3) . ?
C4M H4M1 0.9800 . ?
C4M H4M2 0.9800 . ?
C4M H4M3 0.9800 . ?
C44 O44 1.2051(18) . ?

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
O1 C1 N10 124.18(13) . . ?
O1 C1 C2 120.17(12) . . ?
N10 C1 C2 115.58(12) . . ?
N36 C2 C3 112.10(11) . . ?
N36 C2 C1 107.14(11) . . ?
C3 C2 C1 115.08(11) . . ?
N36 C2 H2 107.4 . . ?
C3 C2 H2 107.4 . . ?
C1 C2 H2 107.4 . . ?
C21 C3 C4 108.70(11) . . ?
C21 C3 C2 111.69(11) . . ?
C4 C3 C2 112.37(11) . . ?
C21 C3 H3 108.0 . . ?
C4 C3 H3 108.0 . . ?
C2 C3 H3 108.0 . . ?
C9 C4 C5 118.88(13) . . ?
C9 C4 C3 119.22(13) . . ?
C5 C4 C3 121.81(12) . . ?
C6 C5 C4 120.48(13) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 120.32(14) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C8 C7 C6 119.35(13) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C7 C8 C9 120.29(14) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C4 C9 C8 120.66(14) . . ?
C4 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C1 N10 C11 127.40(12) . . ?
C1 N10 H10 118.6(12) . . ?
C11 N10 H10 113.9(12) . . ?
C20 C11 N10 125.47(13) . . ?
C20 C11 C12 120.21(13) . . ?
N10 C11 C12 114.32(12) . . ?
N13 C12 C17 123.31(13) . . ?
N13 C12 C11 117.71(12) . . ?
C17 C12 C11 118.98(13) . . ?
C14 N13 C12 117.43(13) . . ?
N13 C14 C15 123.77(15) . . ?
N13 C14 H14 118.1 . . ?
C15 C14 H14 118.1 . . ?
C16 C15 C14 119.22(15) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C15 C16 C17 119.50(14) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C16 C17 C18 123.66(14) . . ?
C16 C17 C12 116.77(14) . . ?
C18 C17 C12 119.57(14) . . ?
C19 C18 C17 119.82(13) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 121.75(14) . . ?
C18 C19 H19 119.1 . . ?
C20 C19 H19 119.1 . . ?
C11 C20 C19 119.66(14) . . ?
C11 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C22 C21 C29 107.33(12) . . ?
C22 C21 C3 128.41(13) . . ?
C29 C21 C3 124.19(12) . . ?
C21 C22 N23 109.89(12) . . ?
C21 C22 H22 125.1 . . ?
N23 C22 H22 125.1 . . ?
C22 N23 C30 120.93(12) . . ?
C22 N23 C24 108.37(11) . . ?
C30 N23 C24 130.47(12) . . ?
C25 C24 N23 131.47(13) . . ?
C25 C24 C29 121.61(13) . . ?
N23 C24 C29 106.92(12) . . ?
C26 C25 C24 117.19(13) . . ?
C26 C25 H25 121.4 . . ?
C24 C25 H25 121.4 . . ?
C25 C26 C27 121.96(13) . . ?
C25 C26 H26 119.0 . . ?
C27 C26 H26 119.0 . . ?
C28 C27 C26 120.85(13) . . ?
C28 C27 H27 119.6 . . ?
C26 C27 H27 119.6 . . ?
C27 C28 C29 118.39(13) . . ?
C27 C28 H28 120.8 . . ?
C29 C28 H28 120.8 . . ?
C28 C29 C24 120.01(13) . . ?
C28 C29 C21 132.51(13) . . ?
C24 C29 C21 107.48(12) . . ?
O30 C30 O31 128.00(14) . . ?
O30 C30 N23 122.02(13) . . ?
O31 C30 N23 109.98(12) . . ?
C30 O31 C32 120.95(11) . . ?
O31 C32 C33 109.40(15) . . ?
O31 C32 C34 109.79(13) . . ?
C33 C32 C34 112.90(14) . . ?
O31 C32 C35 101.09(12) . . ?
C33 C32 C35 112.92(17) . . ?
C34 C32 C35 110.07(17) . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C32 C34 H34A 109.5 . . ?
C32 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C32 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C32 C35 H35A 109.5 . . ?
C32 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C32 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C37 N36 C44 111.39(11) . . ?
C37 N36 C2 122.53(12) . . ?
C44 N36 C2 124.23(12) . . ?
O37 C37 N36 125.46(13) . . ?
O37 C37 C38 128.43(13) . . ?
N36 C37 C38 106.12(12) . . ?
C39 C38 C43 122.00(14) . . ?
C39 C38 C37 129.43(14) . . ?
C43 C38 C37 108.56(12) . . ?
C38 C39 C40 116.81(14) . . ?
C38 C39 H39 121.6 . . ?
C40 C39 H39 121.6 . . ?
C41 C40 C39 121.11(14) . . ?
C41 C40 H40 119.4 . . ?
C39 C40 H40 119.4 . . ?
C40 C41 C42 121.48(14) . . ?
C40 C41 H41 119.3 . . ?
C42 C41 H41 119.3 . . ?
C43 C42 C41 116.99(14) . . ?
C43 C42 H42 121.5 . . ?
C41 C42 H42 121.5 . . ?
C42 C43 C38 121.61(13) . . ?
C42 C43 C44 130.47(13) . . ?
C38 C43 C44 107.92(12) . . ?
C2M O1M H1M 108.1(15) . . ?
O1M C2M H2M1 109.5 . . ?
O1M C2M H2M2 109.5 . . ?
H2M1 C2M H2M2 109.5 . . ?
O1M C2M H2M3 109.5 . . ?
H2M1 C2M H2M3 109.5 . . ?
H2M2 C2M H2M3 109.5 . . ?
C4M O3M H3M 111(2) . . ?
O3M C4M H4M1 109.5 . . ?
O3M C4M H4M2 109.5 . . ?
H4M1 C4M H4M2 109.5 . . ?
O3M C4M H4M3 109.5 . . ?
H4M1 C4M H4M3 109.5 . . ?
H4M2 C4M H4M3 109.5 . . ?
O44 C44 N36 124.65(13) . . ?
O44 C44 C43 129.49(13) . . ?
N36 C44 C43 105.85(12) . . ?

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 C1 C2 N36 2.05(18) . . . . ?
N10 C1 C2 N36 179.02(12) . . . . ?
O1 C1 C2 C3 127.43(14) . . . . ?
N10 C1 C2 C3 -55.59(16) . . . . ?
N36 C2 C3 C21 -163.87(11) . . . . ?
C1 C2 C3 C21 73.37(15) . . . . ?
N36 C2 C3 C4 -41.40(16) . . . . ?
C1 C2 C3 C4 -164.17(11) . . . . ?
C21 C3 C4 C9 -106.90(14) . . . . ?
C2 C3 C4 C9 128.96(13) . . . . ?
C21 C3 C4 C5 69.49(16) . . . . ?
C2 C3 C4 C5 -54.65(17) . . . . ?
C9 C4 C5 C6 0.2(2) . . . . ?
C3 C4 C5 C6 -176.18(13) . . . . ?
C4 C5 C6 C7 0.9(2) . . . . ?
C5 C6 C7 C8 -0.9(2) . . . . ?
C6 C7 C8 C9 -0.3(2) . . . . ?
C5 C4 C9 C8 -1.4(2) . . . . ?
C3 C4 C9 C8 175.09(13) . . . . ?
C7 C8 C9 C4 1.5(2) . . . . ?
O1 C1 N10 C11 0.6(2) . . . . ?
C2 C1 N10 C11 -176.28(13) . . . . ?
C1 N10 C11 C20 5.3(2) . . . . ?
C1 N10 C11 C12 -174.77(13) . . . . ?
C20 C11 C12 N13 179.95(13) . . . . ?
N10 C11 C12 N13 0.02(18) . . . . ?
C20 C11 C12 C17 -0.8(2) . . . . ?
N10 C11 C12 C17 179.30(12) . . . . ?
C17 C12 N13 C14 0.1(2) . . . . ?
C11 C12 N13 C14 179.36(13) . . . . ?
C12 N13 C14 C15 -0.2(2) . . . . ?
N13 C14 C15 C16 -0.2(3) . . . . ?
C14 C15 C16 C17 0.7(2) . . . . ?
C15 C16 C17 C18 179.62(15) . . . . ?
C15 C16 C17 C12 -0.8(2) . . . . ?
N13 C12 C17 C16 0.4(2) . . . . ?
C11 C12 C17 C16 -178.83(13) . . . . ?
N13 C12 C17 C18 179.98(13) . . . . ?
C11 C12 C17 C18 0.7(2) . . . . ?
C16 C17 C18 C19 179.23(15) . . . . ?
C12 C17 C18 C19 -0.3(2) . . . . ?
C17 C18 C19 C20 -0.1(2) . . . . ?
N10 C11 C20 C19 -179.72(14) . . . . ?
C12 C11 C20 C19 0.4(2) . . . . ?
C18 C19 C20 C11 0.1(2) . . . . ?
C4 C3 C21 C22 -84.72(17) . . . . ?
C2 C3 C21 C22 39.82(19) . . . . ?
C4 C3 C21 C29 92.05(15) . . . . ?
C2 C3 C21 C29 -143.41(13) . . . . ?
C29 C21 C22 N23 0.38(15) . . . . ?
C3 C21 C22 N23 177.58(12) . . . . ?
C21 C22 N23 C30 175.08(12) . . . . ?
C21 C22 N23 C24 0.05(15) . . . . ?
C22 N23 C24 C25 -179.69(14) . . . . ?
C30 N23 C24 C25 5.9(2) . . . . ?
C22 N23 C24 C29 -0.47(14) . . . . ?
C30 N23 C24 C29 -174.87(13) . . . . ?
N23 C24 C25 C26 179.38(14) . . . . ?
C29 C24 C25 C26 0.3(2) . . . . ?
C24 C25 C26 C27 -0.2(2) . . . . ?
C25 C26 C27 C28 -0.1(2) . . . . ?
C26 C27 C28 C29 0.4(2) . . . . ?
C27 C28 C29 C24 -0.4(2) . . . . ?
C27 C28 C29 C21 179.67(14) . . . . ?
C25 C24 C29 C28 0.0(2) . . . . ?
N23 C24 C29 C28 -179.28(12) . . . . ?
C25 C24 C29 C21 -179.99(12) . . . . ?
N23 C24 C29 C21 0.70(14) . . . . ?
C22 C21 C29 C28 179.31(14) . . . . ?
C3 C21 C29 C28 2.0(2) . . . . ?
C22 C21 C29 C24 -0.67(15) . . . . ?
C3 C21 C29 C24 -178.02(12) . . . . ?
C22 N23 C30 O30 8.4(2) . . . . ?
C24 N23 C30 O30 -177.84(14) . . . . ?
C22 N23 C30 O31 -171.29(12) . . . . ?
C24 N23 C30 O31 2.5(2) . . . . ?
O30 C30 O31 C32 -2.4(2) . . . . ?
N23 C30 O31 C32 177.26(13) . . . . ?
C30 O31 C32 C33 63.30(18) . . . . ?
C30 O31 C32 C34 -61.12(19) . . . . ?
C30 O31 C32 C35 -177.37(16) . . . . ?
C3 C2 N36 C37 133.73(13) . . . . ?
C1 C2 N36 C37 -99.11(14) . . . . ?
C3 C2 N36 C44 -63.09(17) . . . . ?
C1 C2 N36 C44 64.07(16) . . . . ?
C44 N36 C37 O37 -175.79(14) . . . . ?
C2 N36 C37 O37 -10.7(2) . . . . ?
C44 N36 C37 C38 4.07(15) . . . . ?
C2 N36 C37 C38 169.18(12) . . . . ?
O37 C37 C38 C39 -2.0(3) . . . . ?
N36 C37 C38 C39 178.09(14) . . . . ?
O37 C37 C38 C43 177.05(14) . . . . ?
N36 C37 C38 C43 -2.81(15) . . . . ?
C43 C38 C39 C40 -0.4(2) . . . . ?
C37 C38 C39 C40 178.62(14) . . . . ?
C38 C39 C40 C41 0.0(2) . . . . ?
C39 C40 C41 C42 0.6(2) . . . . ?
C40 C41 C42 C43 -0.7(2) . . . . ?
C41 C42 C43 C38 0.3(2) . . . . ?
C41 C42 C43 C44 -179.12(14) . . . . ?
C39 C38 C43 C42 0.3(2) . . . . ?
C37 C38 C43 C42 -178.92(13) . . . . ?
C39 C38 C43 C44 179.78(13) . . . . ?
C37 C38 C43 C44 0.60(15) . . . . ?
C37 N36 C44 O44 176.96(13) . . . . ?
C2 N36 C44 O44 12.2(2) . . . . ?
C37 N36 C44 C43 -3.72(15) . . . . ?
C2 N36 C44 C43 -168.52(12) . . . . ?
C42 C43 C44 O44 0.6(3) . . . . ?
C38 C43 C44 O44 -178.91(14) . . . . ?
C42 C43 C44 N36 -178.73(14) . . . . ?
C38 C43 C44 N36 1.81(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1M H1M O44 0.94(3) 2.20(3) 2.9977(16) 142(2) . yes
O3M H3M O37 0.93(3) 1.90(3) 2.8066(19) 165(3) . yes

_refine_diff_density_max         0.558
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_LN513
_database_code_depnum_ccdc_archive 'CCDC 1903901'
loop_
_audit_author_name
_audit_author_address
'Klaus Harms'
;University of Marburg
Germany
;
_audit_update_record             
;
2019-03-18 deposited with the CCDC.	2019-08-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H17 N3 O4'
_chemical_formula_sum            'C21 H17 N3 O4'
_chemical_formula_weight         375.38

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'
H H 0.0000 0.0000 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.5853(4)
_cell_length_b                   7.0808(2)
_cell_length_c                   14.4608(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.828(4)
_cell_angle_gamma                90
_cell_volume                     872.85(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    18991
_cell_measurement_theta_min      5.19
_cell_measurement_theta_max      71.53

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.69
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    0.833
_shelx_estimated_absorpt_T_min   0.597
_shelx_estimated_absorpt_T_max   0.944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1720
_exptl_absorpt_correction_T_max  0.7847
_exptl_absorpt_process_details   
'STOE LANA, absorption correction by scaling of reflection intensities.'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_type           CuK\a
_diffrn_source                   'GeniX 3D HF Cu'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_detector_area_resol_mean 5.81
_diffrn_reflns_number            14642
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         5.189
_diffrn_reflns_theta_max         71.573
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             3282
_reflns_number_gt                3030
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.796
_reflns_Friedel_fraction_max     0.930
_reflns_Friedel_fraction_full    0.957

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'X-Area Pilatus3_SV 1.31.127.0 (STOE, 2016)'
_computing_cell_refinement       'X-Area Recipe 1.33.0.0 (STOE, 2015)'
_computing_data_reduction        
'X-Area Integrate 1.71.0.0 (STOE, 2016) X-Area LANA 1.68.2.0 (STOE, 2016)'
_computing_structure_solution    'XT V2014/1 (Bruker AXS Inc., 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact)'
_computing_publication_material  'X-Area 1.77'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0620P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1266 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.09(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3282
_refine_ls_number_parameters     264
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0312
_refine_ls_wR_factor_ref         0.0844
_refine_ls_wR_factor_gt          0.0829
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8113(3) 0.6873(3) 0.54822(15) 0.0252(5) Uani 1 1 d . . . . .
O1 O 0.94926(18) 0.6789(3) 0.57823(11) 0.0340(4) Uani 1 1 d . . . . .
N2 N 0.6810(2) 0.6909(3) 0.60225(12) 0.0225(4) Uani 1 1 d . . . . .
O2 O 0.56422(18) 0.6373(3) 0.73147(10) 0.0279(4) Uani 1 1 d . . . . .
C3 C 0.5390(3) 0.6975(3) 0.54054(14) 0.0217(4) Uani 1 1 d . . . . .
O3 O 0.96171(19) 0.2954(2) 0.81322(11) 0.0267(4) Uani 1 1 d . . . . .
C4 C 0.3822(3) 0.7030(3) 0.55296(15) 0.0236(4) Uani 1 1 d . . . . .
H4 H 0.348660 0.703140 0.613242 0.028 Uiso 1 1 calc R U . . .
O4 O 0.6865(2) 0.7883(2) 0.92026(11) 0.0290(4) Uani 1 1 d . . . . .
C5 C 0.2750(3) 0.7085(3) 0.47192(16) 0.0273(5) Uani 1 1 d . . . . .
H5 H 0.165990 0.713645 0.477767 0.033 Uiso 1 1 calc R U . . .
C6 C 0.3224(3) 0.7066(3) 0.38353(15) 0.0264(5) Uani 1 1 d . . . . .
H6 H 0.245427 0.709891 0.330601 0.032 Uiso 1 1 calc R U . . .
C7 C 0.4807(3) 0.7001(3) 0.37084(15) 0.0248(5) Uani 1 1 d . . . . .
C8 C 0.5511(3) 0.6906(4) 0.28036(15) 0.0318(5) Uani 1 1 d . . . . .
H8A H 0.551173 0.557853 0.258844 0.038 Uiso 0.722(9) 1 calc R U P A 1
H8B H 0.485749 0.765190 0.232503 0.038 Uiso 0.722(9) 1 calc R U P A 1
H8C H 0.544961 0.816696 0.250597 0.038 Uiso 0.278(9) 1 calc R U P A 2
H8D H 0.489740 0.601267 0.237714 0.038 Uiso 0.278(9) 1 calc R U P A 2
C10 C 0.8253(3) 0.6857(4) 0.37412(16) 0.0355(6) Uani 1 1 d . . . . .
H10A H 0.854131 0.553626 0.361551 0.043 Uiso 0.722(9) 1 calc R U P A 1
H10B H 0.922462 0.762121 0.383024 0.043 Uiso 0.722(9) 1 calc R U P A 1
H10C H 0.863892 0.813666 0.361236 0.043 Uiso 0.278(9) 1 calc R U P A 2
H10D H 0.917703 0.601880 0.386259 0.043 Uiso 0.278(9) 1 calc R U P A 2
N11 N 0.7454(2) 0.6938(3) 0.45818(12) 0.0246(4) Uani 1 1 d . . . . .
C12 C 0.5833(3) 0.6981(3) 0.45199(15) 0.0221(5) Uani 1 1 d . . . . .
C13 C 0.6852(3) 0.6602(3) 0.69792(15) 0.0226(5) Uani 1 1 d . . . . .
C14 C 0.8446(3) 0.6625(3) 0.75720(14) 0.0234(5) Uani 1 1 d . . . . .
H14 H 0.920717 0.589498 0.723922 0.028 Uiso 1 1 calc R U . . .
C15 C 0.9053(3) 0.8654(3) 0.77138(17) 0.0291(5) Uani 1 1 d . . . . .
H15A H 1.001008 0.865582 0.815637 0.044 Uiso 1 1 calc R U . . .
H15B H 0.825128 0.943199 0.795908 0.044 Uiso 1 1 calc R U . . .
H15C H 0.928344 0.917140 0.711639 0.044 Uiso 1 1 calc R U . . .
N16 N 0.8273(2) 0.5668(3) 0.84495(12) 0.0231(4) Uani 1 1 d . . . . .
C17 C 0.8824(3) 0.3828(3) 0.86253(15) 0.0223(5) Uani 1 1 d . . . . .
C18 C 0.8231(2) 0.3232(3) 0.95086(14) 0.0230(5) Uani 1 1 d . . . . .
C19 C 0.8379(3) 0.1527(3) 0.99683(15) 0.0258(5) Uani 1 1 d . . . . .
H19 H 0.898107 0.052408 0.975704 0.031 Uiso 1 1 calc R U . . .
C20 C 0.7605(3) 0.1341(4) 1.07580(16) 0.0306(5) Uani 1 1 d . . . . .
H20 H 0.767593 0.018285 1.109213 0.037 Uiso 1 1 calc R U . . .
C21 C 0.6731(3) 0.2819(4) 1.10660(16) 0.0312(5) Uani 1 1 d . . . . .
H21 H 0.621823 0.265258 1.160717 0.037 Uiso 1 1 calc R U . . .
C22 C 0.6596(3) 0.4542(4) 1.05934(15) 0.0284(5) Uani 1 1 d . . . . .
H22 H 0.599752 0.555376 1.079993 0.034 Uiso 1 1 calc R U . . .
C23 C 0.7370(3) 0.4711(3) 0.98119(15) 0.0241(5) Uani 1 1 d . . . . .
C24 C 0.7411(3) 0.6324(3) 0.91549(15) 0.0242(5) Uani 1 1 d . . . . .
C9 C 0.7130(4) 0.7642(6) 0.2907(2) 0.0288(11) Uani 0.722(9) 1 d . U P A 1
H9A H 0.708337 0.903233 0.296991 0.035 Uiso 0.722(9) 1 calc R U P A 1
H9AB H 0.759318 0.736592 0.232694 0.035 Uiso 0.722(9) 1 calc R U P A 1
C9A C 0.7334(10) 0.6222(15) 0.2967(6) 0.030(3) Uani 0.278(9) 1 d . U P A 2
H9AA H 0.734257 0.482477 0.298528 0.037 Uiso 0.278(9) 1 calc R U P A 2
H9AC H 0.783685 0.660785 0.241505 0.037 Uiso 0.278(9) 1 calc R U P A 2


_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
C1 O1 1.213(3) . ?
C1 N11 1.357(3) . ?
C1 N2 1.439(3) . ?
N2 C13 1.397(3) . ?
N2 C3 1.423(3) . ?
O2 C13 1.208(3) . ?
C3 C12 1.378(3) . ?
C3 C4 1.380(3) . ?
O3 C17 1.213(3) . ?
C4 C5 1.402(3) . ?
C4 H4 0.9500 . ?
O4 C24 1.204(3) . ?
C5 C6 1.387(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.394(3) . ?
C6 H6 0.9500 . ?
C7 C12 1.381(3) . ?
C7 C8 1.506(3) . ?
C8 C9 1.476(4) . ?
C8 C9A 1.629(9) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 H8C 0.9900 . ?
C8 H8D 0.9900 . ?
C10 C9A 1.367(9) . ?
C10 N11 1.466(3) . ?
C10 C9 1.554(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 H10C 0.9900 . ?
C10 H10D 0.9900 . ?
N11 C12 1.384(3) . ?
C13 C14 1.527(3) . ?
C14 N16 1.462(3) . ?
C14 C15 1.534(3) . ?
C14 H14 1.0000 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
N16 C17 1.399(3) . ?
N16 C24 1.409(3) . ?
C17 C18 1.491(3) . ?
C18 C19 1.376(3) . ?
C18 C23 1.383(3) . ?
C19 C20 1.394(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.391(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.397(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.383(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.489(3) . ?
C9 H9A 0.9900 . ?
C9 H9AB 0.9900 . ?
C9A H9AA 0.9900 . ?
C9A H9AC 0.9900 . ?

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
O1 C1 N11 128.5(2) . . ?
O1 C1 N2 126.5(2) . . ?
N11 C1 N2 104.91(19) . . ?
C13 N2 C3 123.05(18) . . ?
C13 N2 C1 127.23(19) . . ?
C3 N2 C1 108.87(17) . . ?
C12 C3 C4 120.13(18) . . ?
C12 C3 N2 105.80(18) . . ?
C4 C3 N2 134.07(19) . . ?
C3 C4 C5 116.5(2) . . ?
C3 C4 H4 121.8 . . ?
C5 C4 H4 121.8 . . ?
C6 C5 C4 122.3(2) . . ?
C6 C5 H5 118.8 . . ?
C4 C5 H5 118.8 . . ?
C5 C6 C7 121.29(19) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C12 C7 C6 115.0(2) . . ?
C12 C7 C8 117.2(2) . . ?
C6 C7 C8 127.87(19) . . ?
C9 C8 C7 111.5(2) . . ?
C7 C8 C9A 111.4(3) . . ?
C9 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C7 C8 H8C 109.3 . . ?
C9A C8 H8C 109.3 . . ?
C7 C8 H8D 109.3 . . ?
C9A C8 H8D 109.3 . . ?
H8C C8 H8D 108.0 . . ?
C9A C10 N11 114.2(4) . . ?
N11 C10 C9 108.7(2) . . ?
N11 C10 H10A 109.9 . . ?
C9 C10 H10A 109.9 . . ?
N11 C10 H10B 109.9 . . ?
C9 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
C9A C10 H10C 108.7 . . ?
N11 C10 H10C 108.7 . . ?
C9A C10 H10D 108.7 . . ?
N11 C10 H10D 108.7 . . ?
H10C C10 H10D 107.6 . . ?
C1 N11 C12 111.37(19) . . ?
C1 N11 C10 127.65(19) . . ?
C12 N11 C10 120.87(18) . . ?
C3 C12 C7 124.8(2) . . ?
C3 C12 N11 109.03(18) . . ?
C7 C12 N11 126.1(2) . . ?
O2 C13 N2 119.8(2) . . ?
O2 C13 C14 122.2(2) . . ?
N2 C13 C14 118.05(18) . . ?
N16 C14 C13 107.80(18) . . ?
N16 C14 C15 112.72(18) . . ?
C13 C14 C15 110.62(18) . . ?
N16 C14 H14 108.5 . . ?
C13 C14 H14 108.5 . . ?
C15 C14 H14 108.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 N16 C24 111.78(18) . . ?
C17 N16 C14 121.50(18) . . ?
C24 N16 C14 126.32(19) . . ?
O3 C17 N16 124.7(2) . . ?
O3 C17 C18 129.2(2) . . ?
N16 C17 C18 106.08(19) . . ?
C19 C18 C23 122.2(2) . . ?
C19 C18 C17 129.8(2) . . ?
C23 C18 C17 107.9(2) . . ?
C18 C19 C20 116.9(2) . . ?
C18 C19 H19 121.5 . . ?
C20 C19 H19 121.5 . . ?
C21 C20 C19 121.2(2) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C20 C21 C22 121.2(2) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 H21 119.4 . . ?
C23 C22 C21 117.1(2) . . ?
C23 C22 H22 121.5 . . ?
C21 C22 H22 121.5 . . ?
C22 C23 C18 121.4(2) . . ?
C22 C23 C24 129.7(2) . . ?
C18 C23 C24 108.9(2) . . ?
O4 C24 N16 125.8(2) . . ?
O4 C24 C23 128.9(2) . . ?
N16 C24 C23 105.28(19) . . ?
C8 C9 C10 116.3(3) . . ?
C8 C9 H9A 108.2 . . ?
C10 C9 H9A 108.2 . . ?
C8 C9 H9AB 108.2 . . ?
C10 C9 H9AB 108.2 . . ?
H9A C9 H9AB 107.4 . . ?
C10 C9A C8 118.2(6) . . ?
C10 C9A H9AA 107.8 . . ?
C8 C9A H9AA 107.8 . . ?
C10 C9A H9AC 107.8 . . ?
C8 C9A H9AC 107.8 . . ?
H9AA C9A H9AC 107.1 . . ?

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 C1 N2 C13 -9.3(4) . . . . ?
N11 C1 N2 C13 170.2(2) . . . . ?
O1 C1 N2 C3 -178.9(2) . . . . ?
N11 C1 N2 C3 0.6(2) . . . . ?
C13 N2 C3 C12 -170.20(19) . . . . ?
C1 N2 C3 C12 -0.1(2) . . . . ?
C13 N2 C3 C4 9.9(4) . . . . ?
C1 N2 C3 C4 180.0(2) . . . . ?
C12 C3 C4 C5 0.2(3) . . . . ?
N2 C3 C4 C5 -179.9(2) . . . . ?
C3 C4 C5 C6 0.6(4) . . . . ?
C4 C5 C6 C7 -0.3(4) . . . . ?
C5 C6 C7 C12 -0.8(3) . . . . ?
C5 C6 C7 C8 177.7(2) . . . . ?
C12 C7 C8 C9 -25.4(3) . . . . ?
C6 C7 C8 C9 156.2(3) . . . . ?
C12 C7 C8 C9A 15.6(5) . . . . ?
C6 C7 C8 C9A -162.8(4) . . . . ?
O1 C1 N11 C12 178.6(2) . . . . ?
N2 C1 N11 C12 -1.0(3) . . . . ?
O1 C1 N11 C10 2.3(4) . . . . ?
N2 C1 N11 C10 -177.2(2) . . . . ?
C9A C10 N11 C1 155.7(5) . . . . ?
C9 C10 N11 C1 -161.2(3) . . . . ?
C9A C10 N11 C12 -20.2(6) . . . . ?
C9 C10 N11 C12 22.9(3) . . . . ?
C4 C3 C12 C7 -1.4(4) . . . . ?
N2 C3 C12 C7 178.7(2) . . . . ?
C4 C3 C12 N11 179.4(2) . . . . ?
N2 C3 C12 N11 -0.5(2) . . . . ?
C6 C7 C12 C3 1.6(3) . . . . ?
C8 C7 C12 C3 -177.0(2) . . . . ?
C6 C7 C12 N11 -179.3(2) . . . . ?
C8 C7 C12 N11 2.1(3) . . . . ?
C1 N11 C12 C3 1.0(3) . . . . ?
C10 N11 C12 C3 177.5(2) . . . . ?
C1 N11 C12 C7 -178.2(2) . . . . ?
C10 N11 C12 C7 -1.7(4) . . . . ?
C3 N2 C13 O2 0.3(3) . . . . ?
C1 N2 C13 O2 -168.0(2) . . . . ?
C3 N2 C13 C14 -178.1(2) . . . . ?
C1 N2 C13 C14 13.7(3) . . . . ?
O2 C13 C14 N16 20.6(3) . . . . ?
N2 C13 C14 N16 -161.10(18) . . . . ?
O2 C13 C14 C15 -103.1(3) . . . . ?
N2 C13 C14 C15 75.2(2) . . . . ?
C13 C14 N16 C17 103.8(2) . . . . ?
C15 C14 N16 C17 -133.8(2) . . . . ?
C13 C14 N16 C24 -68.2(3) . . . . ?
C15 C14 N16 C24 54.1(3) . . . . ?
C24 N16 C17 O3 -178.8(2) . . . . ?
C14 N16 C17 O3 8.1(3) . . . . ?
C24 N16 C17 C18 1.5(2) . . . . ?
C14 N16 C17 C18 -171.62(18) . . . . ?
O3 C17 C18 C19 -2.7(4) . . . . ?
N16 C17 C18 C19 176.9(2) . . . . ?
O3 C17 C18 C23 -179.6(2) . . . . ?
N16 C17 C18 C23 0.1(2) . . . . ?
C23 C18 C19 C20 0.6(3) . . . . ?
C17 C18 C19 C20 -175.9(2) . . . . ?
C18 C19 C20 C21 -0.3(3) . . . . ?
C19 C20 C21 C22 0.1(4) . . . . ?
C20 C21 C22 C23 -0.2(3) . . . . ?
C21 C22 C23 C18 0.5(3) . . . . ?
C21 C22 C23 C24 178.0(2) . . . . ?
C19 C18 C23 C22 -0.7(3) . . . . ?
C17 C18 C23 C22 176.50(19) . . . . ?
C19 C18 C23 C24 -178.67(19) . . . . ?
C17 C18 C23 C24 -1.5(2) . . . . ?
C17 N16 C24 O4 176.4(2) . . . . ?
C14 N16 C24 O4 -10.9(4) . . . . ?
C17 N16 C24 C23 -2.4(2) . . . . ?
C14 N16 C24 C23 170.33(19) . . . . ?
C22 C23 C24 O4 5.9(4) . . . . ?
C18 C23 C24 O4 -176.3(2) . . . . ?
C22 C23 C24 N16 -175.4(2) . . . . ?
C18 C23 C24 N16 2.4(2) . . . . ?
C7 C8 C9 C10 49.3(4) . . . . ?
N11 C10 C9 C8 -47.6(4) . . . . ?
N11 C10 C9A C8 39.3(8) . . . . ?
C7 C8 C9A C10 -38.0(8) . . . . ?

_refine_diff_density_max         0.176
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.038

