# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_FO5912
_database_code_depnum_ccdc_archive 'CCDC 1505093'
_audit_update_record             
;
2018-01-29 deposited with the CCDC.
2018-04-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C49 H36 Cl2 Co N4 O'
_chemical_formula_sum            'C49 H36 Cl2 Co N4 O'
_chemical_formula_weight         826.65

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 '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'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   10.9294(4)
_cell_length_b                   11.1711(3)
_cell_length_c                   17.8224(4)
_cell_angle_alpha                75.494(2)
_cell_angle_beta                 83.788(2)
_cell_angle_gamma                71.540(1)
_cell_volume                     1997.2(1)
_cell_formula_units_Z            2
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    15767
_cell_measurement_theta_min      1.97
_cell_measurement_theta_max      27.10

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.102
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.088
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             854
_exptl_absorpt_coefficient_mu    0.607
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6901
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS, Bruker-AXS, 2002'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      133(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  KappaCCD
_diffrn_measurement_method       'phi- + omega-scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15767
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0407
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         27.10
_reflns_number_total             8649
_reflns_number_gt                7181
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       COLLECT
_computing_cell_refinement       DENZO
_computing_data_reduction        DENZO
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXL-97

_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)+(0.0151P)²+3.4302P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8649
_refine_ls_number_parameters     647
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1063
_refine_ls_wR_factor_gt          0.0981
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_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
Co1 Co 0.27130(3) 0.37413(3) 0.75153(2) 0.02177(9) Uani 1 1 d . . .
Cl1 Cl 0.17755(8) 0.56961(7) 0.77605(4) 0.04005(19) Uani 1 1 d . . .
Cl2 Cl 0.16004(8) 0.29146(8) 0.69159(4) 0.03981(19) Uani 1 1 d . . .
O1 O 0.41586(16) 0.38166(16) 0.67384(9) 0.0215(4) Uani 1 1 d . . .
N1 N 0.3928(2) 0.2502(2) 0.83419(12) 0.0226(4) Uani 1 1 d . . .
N2 N 0.5931(2) 0.1766(2) 0.87342(12) 0.0229(4) Uani 1 1 d . . .
N3 N 0.3737(2) 0.4270(2) 0.53448(12) 0.0221(4) Uani 1 1 d . . .
H1N3 H 0.359(3) 0.441(3) 0.586(2) 0.047(10) Uiso 1 1 d . . .
N4 N 0.4804(2) 0.3187(2) 0.45108(11) 0.0209(4) Uani 1 1 d . . .
C1 C 0.5040(2) 0.2705(2) 0.66805(14) 0.0203(5) Uani 1 1 d . . .
C2 C 0.5438(2) 0.2377(2) 0.59462(14) 0.0210(5) Uani 1 1 d . . .
C3 C 0.6407(3) 0.1214(3) 0.59151(15) 0.0241(5) Uani 1 1 d . . .
H3 H 0.668(2) 0.101(2) 0.5434(15) 0.014(6) Uiso 1 1 d . . .
C4 C 0.6970(3) 0.0345(3) 0.65739(15) 0.0251(5) Uani 1 1 d . . .
C5 C 0.6554(3) 0.0646(3) 0.72906(15) 0.0245(5) Uani 1 1 d . . .
H5 H 0.694(3) 0.004(3) 0.7745(16) 0.021(7) Uiso 1 1 d . . .
C6 C 0.5615(2) 0.1803(2) 0.73523(14) 0.0213(5) Uani 1 1 d . . .
C7 C 0.7999(3) -0.0910(3) 0.65248(17) 0.0355(7) Uani 1 1 d . . .
H7B H 0.8525 -0.1218 0.6986 0.053 Uiso 1 1 calc R . .
H7C H 0.8549 -0.0765 0.6060 0.053 Uiso 1 1 calc R . .
H7A H 0.7591 -0.1562 0.6496 0.053 Uiso 1 1 calc R . .
C8 C 0.5159(2) 0.2052(2) 0.81243(14) 0.0216(5) Uani 1 1 d . . .
C9 C 0.3896(2) 0.2462(3) 0.91302(14) 0.0232(5) Uani 1 1 d . . .
C10 C 0.5132(3) 0.2035(3) 0.93794(14) 0.0237(5) Uani 1 1 d . . .
C11 C 0.2642(3) 0.2808(3) 0.95523(15) 0.0264(6) Uani 1 1 d . . .
C12 C 0.1532(3) 0.2794(3) 0.92424(16) 0.0294(6) Uani 1 1 d . . .
H12 H 0.161(3) 0.254(3) 0.8777(18) 0.031(8) Uiso 1 1 d . . .
C13 C 0.0346(3) 0.3103(3) 0.96289(18) 0.0361(7) Uani 1 1 d . . .
H13 H -0.043(3) 0.310(3) 0.9391(18) 0.040(9) Uiso 1 1 d . . .
C14 C 0.0251(3) 0.3393(3) 1.0347(2) 0.0425(8) Uani 1 1 d . . .
H14 H -0.059(4) 0.363(3) 1.064(2) 0.055(11) Uiso 1 1 d . . .
C15 C 0.1341(3) 0.3377(4) 1.0676(2) 0.0441(8) Uani 1 1 d . . .
H15 H 0.129(4) 0.357(4) 1.121(2) 0.069(12) Uiso 1 1 d . . .
C16 C 0.2535(3) 0.3096(3) 1.02818(17) 0.0357(7) Uani 1 1 d . . .
H16 H 0.331(3) 0.314(3) 1.0491(19) 0.044(9) Uiso 1 1 d . . .
C17 C 0.5693(2) 0.1951(3) 1.01184(15) 0.0254(5) Uani 1 1 d . . .
C18 C 0.5626(3) 0.0996(3) 1.07790(17) 0.0378(7) Uani 1 1 d . . .
H18 H 0.521(3) 0.041(3) 1.0745(17) 0.034(8) Uiso 1 1 d . . .
C19 C 0.6153(4) 0.0960(4) 1.14594(19) 0.0462(9) Uani 1 1 d . . .
H19 H 0.608(4) 0.037(4) 1.186(2) 0.056(11) Uiso 1 1 d . . .
C20 C 0.6754(3) 0.1860(3) 1.14866(18) 0.0400(8) Uani 1 1 d . . .
H20 H 0.708(3) 0.186(3) 1.195(2) 0.046(10) Uiso 1 1 d . . .
C21 C 0.6831(3) 0.2807(3) 1.08358(18) 0.0364(7) Uani 1 1 d . . .
H21 H 0.725(3) 0.343(3) 1.0850(19) 0.043(9) Uiso 1 1 d . . .
C22 C 0.6304(3) 0.2849(3) 1.01525(16) 0.0315(6) Uani 1 1 d . . .
H22 H 0.639(3) 0.347(3) 0.9712(18) 0.030(8) Uiso 1 1 d . . .
C26 C 0.7316(2) 0.1401(3) 0.86965(14) 0.0239(5) Uani 1 1 d . . .
C27 C 0.8041(3) 0.0287(3) 0.91802(17) 0.0331(6) Uani 1 1 d . . .
H27 H 0.764(3) -0.026(3) 0.9497(16) 0.024(7) Uiso 1 1 d . . .
C28 C 0.9383(3) -0.0032(3) 0.9106(2) 0.0415(8) Uani 1 1 d . . .
H28 H 0.983(3) -0.078(3) 0.945(2) 0.045(10) Uiso 1 1 d . . .
C29 C 0.9962(3) 0.0743(3) 0.8567(2) 0.0406(8) Uani 1 1 d . . .
H29 H 1.089(4) 0.051(3) 0.851(2) 0.050(10) Uiso 1 1 d . . .
C30 C 0.9231(3) 0.1854(3) 0.80913(18) 0.0361(7) Uani 1 1 d . . .
H30 H 0.966(4) 0.240(3) 0.774(2) 0.054(11) Uiso 1 1 d . . .
C31 C 0.7902(3) 0.2189(3) 0.81605(15) 0.0268(6) Uani 1 1 d . . .
H31 H 0.740(3) 0.299(3) 0.7846(18) 0.035(8) Uiso 1 1 d . . .
C32 C 0.4735(2) 0.3242(2) 0.52719(14) 0.0210(5) Uani 1 1 d . . .
C33 C 0.3113(2) 0.4869(2) 0.46557(14) 0.0224(5) Uani 1 1 d . . .
C34 C 0.3785(2) 0.4195(2) 0.41200(14) 0.0218(5) Uani 1 1 d . . .
C35 C 0.1954(2) 0.5984(2) 0.46394(14) 0.0225(5) Uani 1 1 d . . .
C36 C 0.1675(3) 0.7034(3) 0.40013(15) 0.0253(5) Uani 1 1 d . . .
H36 H 0.224(3) 0.702(3) 0.3555(18) 0.033(8) Uiso 1 1 d . . .
C37 C 0.0599(3) 0.8089(3) 0.40264(17) 0.0302(6) Uani 1 1 d . . .
H37 H 0.041(3) 0.878(3) 0.3596(17) 0.030(8) Uiso 1 1 d . . .
C38 C -0.0199(3) 0.8114(3) 0.46842(17) 0.0350(7) Uani 1 1 d . . .
H38 H -0.092(3) 0.880(3) 0.4700(18) 0.037(9) Uiso 1 1 d . . .
C39 C 0.0065(3) 0.7078(3) 0.53166(18) 0.0376(7) Uani 1 1 d . . .
H39 H -0.044(4) 0.708(3) 0.577(2) 0.054(11) Uiso 1 1 d . . .
C40 C 0.1132(3) 0.6003(3) 0.52962(16) 0.0305(6) Uani 1 1 d . . .
H40 H 0.128(3) 0.525(3) 0.5757(17) 0.030(8) Uiso 1 1 d . . .
C41 C 0.3504(2) 0.4352(2) 0.33057(14) 0.0225(5) Uani 1 1 d . . .
C42 C 0.4449(3) 0.4369(3) 0.27094(15) 0.0258(5) Uani 1 1 d . . .
H42 H 0.527(3) 0.429(3) 0.2817(16) 0.024(7) Uiso 1 1 d . . .
C43 C 0.4124(3) 0.4519(3) 0.19537(16) 0.0304(6) Uani 1 1 d . . .
H43 H 0.475(3) 0.458(3) 0.1554(18) 0.033(8) Uiso 1 1 d . . .
C44 C 0.2874(3) 0.4672(3) 0.17815(17) 0.0339(7) Uani 1 1 d . . .
H44 H 0.267(3) 0.476(3) 0.1254(18) 0.035(8) Uiso 1 1 d . . .
C45 C 0.1924(3) 0.4671(3) 0.23676(17) 0.0326(6) Uani 1 1 d . . .
H45 H 0.107(3) 0.475(3) 0.2261(18) 0.040(9) Uiso 1 1 d . . .
C46 C 0.2240(3) 0.4515(3) 0.31268(16) 0.0278(6) Uani 1 1 d . . .
H46 H 0.159(3) 0.450(3) 0.3536(16) 0.023(7) Uiso 1 1 d . . .
C47 C 0.5709(2) 0.2205(2) 0.41585(13) 0.0208(5) Uani 1 1 d . . .
C48 C 0.6917(3) 0.2321(3) 0.39181(15) 0.0265(6) Uani 1 1 d . . .
H48 H 0.718(3) 0.306(3) 0.3958(17) 0.031(8) Uiso 1 1 d . . .
C49 C 0.7774(3) 0.1380(3) 0.35792(16) 0.0294(6) Uani 1 1 d . . .
H49 H 0.860(3) 0.150(3) 0.3406(17) 0.035(8) Uiso 1 1 d . . .
C50 C 0.7411(3) 0.0350(3) 0.34795(16) 0.0300(6) Uani 1 1 d . . .
H50 H 0.799(3) -0.031(3) 0.3237(18) 0.040(9) Uiso 1 1 d . . .
C51 C 0.6196(3) 0.0253(3) 0.37171(16) 0.0297(6) Uani 1 1 d . . .
H51 H 0.598(3) -0.042(3) 0.3671(16) 0.027(8) Uiso 1 1 d . . .
C52 C 0.5327(3) 0.1187(3) 0.40596(15) 0.0261(6) Uani 1 1 d . . .
H52 H 0.450(3) 0.114(3) 0.4233(16) 0.023(7) Uiso 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
Co1 O1 1.9932(17) . ?
Co1 N1 2.022(2) . ?
Co1 Cl2 2.2269(8) . ?
Co1 Cl1 2.2302(8) . ?
O1 C1 1.328(3) . ?
N1 C8 1.331(3) . ?
N1 C9 1.391(3) . ?
N2 C8 1.359(3) . ?
N2 C10 1.402(3) . ?
N2 C26 1.437(3) . ?
N3 C32 1.333(3) . ?
N3 C33 1.379(3) . ?
N3 H1N3 0.96(3) . ?
N4 C32 1.366(3) . ?
N4 C34 1.405(3) . ?
N4 C47 1.449(3) . ?
C1 C6 1.415(3) . ?
C1 C2 1.433(3) . ?
C2 C3 1.402(4) . ?
C2 C32 1.454(3) . ?
C3 C4 1.381(4) . ?
C3 H3 0.93(3) . ?
C4 C5 1.394(4) . ?
C4 C7 1.510(4) . ?
C5 C6 1.394(4) . ?
C5 H5 0.95(3) . ?
C6 C8 1.474(3) . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C7 H7A 0.9800 . ?
C9 C10 1.366(4) . ?
C9 C11 1.477(4) . ?
C10 C17 1.482(3) . ?
C11 C12 1.392(4) . ?
C11 C16 1.400(4) . ?
C12 C13 1.384(4) . ?
C12 H12 0.93(3) . ?
C13 C14 1.382(4) . ?
C13 H13 0.99(3) . ?
C14 C15 1.377(5) . ?
C14 H14 1.00(4) . ?
C15 C16 1.396(4) . ?
C15 H15 1.03(4) . ?
C16 H16 0.98(3) . ?
C17 C22 1.385(4) . ?
C17 C18 1.390(4) . ?
C18 C19 1.384(4) . ?
C18 H18 0.92(3) . ?
C19 C20 1.376(5) . ?
C19 H19 0.85(4) . ?
C20 C21 1.376(5) . ?
C20 H20 0.94(3) . ?
C21 C22 1.387(4) . ?
C21 H21 0.96(3) . ?
C22 H22 0.92(3) . ?
C26 C31 1.378(4) . ?
C26 C27 1.380(4) . ?
C27 C28 1.395(4) . ?
C27 H27 0.91(3) . ?
C28 C29 1.369(5) . ?
C28 H28 0.92(3) . ?
C29 C30 1.374(5) . ?
C29 H29 0.97(4) . ?
C30 C31 1.381(4) . ?
C30 H30 0.96(4) . ?
C31 H31 0.96(3) . ?
C33 C34 1.369(3) . ?
C33 C35 1.466(3) . ?
C34 C41 1.472(3) . ?
C35 C36 1.394(4) . ?
C35 C40 1.397(4) . ?
C36 C37 1.382(4) . ?
C36 H36 0.95(3) . ?
C37 C38 1.384(4) . ?
C37 H37 0.93(3) . ?
C38 C39 1.378(4) . ?
C38 H38 0.92(3) . ?
C39 C40 1.389(4) . ?
C39 H39 0.93(4) . ?
C40 H40 1.00(3) . ?
C41 C46 1.397(4) . ?
C41 C42 1.400(4) . ?
C42 C43 1.386(4) . ?
C42 H42 0.91(3) . ?
C43 C44 1.381(4) . ?
C43 H43 0.94(3) . ?
C44 C45 1.391(4) . ?
C44 H44 0.96(3) . ?
C45 C46 1.387(4) . ?
C45 H45 0.95(3) . ?
C46 H46 0.96(3) . ?
C47 C48 1.379(4) . ?
C47 C52 1.384(4) . ?
C48 C49 1.386(4) . ?
C48 H48 0.97(3) . ?
C49 C50 1.385(4) . ?
C49 H49 0.96(3) . ?
C50 C51 1.379(4) . ?
C50 H50 0.97(3) . ?
C51 C52 1.389(4) . ?
C51 H51 0.88(3) . ?
C52 H52 0.94(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
O1 Co1 N1 92.16(8) . . ?
O1 Co1 Cl2 99.30(5) . . ?
N1 Co1 Cl2 117.54(7) . . ?
O1 Co1 Cl1 109.65(5) . . ?
N1 Co1 Cl1 113.80(6) . . ?
Cl2 Co1 Cl1 118.94(4) . . ?
C1 O1 Co1 117.70(15) . . ?
C8 N1 C9 107.3(2) . . ?
C8 N1 Co1 116.91(16) . . ?
C9 N1 Co1 129.10(17) . . ?
C8 N2 C10 107.7(2) . . ?
C8 N2 C26 125.6(2) . . ?
C10 N2 C26 126.3(2) . . ?
C32 N3 C33 111.6(2) . . ?
C32 N3 H1N3 114(2) . . ?
C33 N3 H1N3 134(2) . . ?
C32 N4 C34 109.0(2) . . ?
C32 N4 C47 126.6(2) . . ?
C34 N4 C47 124.2(2) . . ?
O1 C1 C6 120.4(2) . . ?
O1 C1 C2 121.8(2) . . ?
C6 C1 C2 117.9(2) . . ?
C3 C2 C1 119.4(2) . . ?
C3 C2 C32 123.2(2) . . ?
C1 C2 C32 117.2(2) . . ?
C4 C3 C2 122.2(2) . . ?
C4 C3 H3 118.7(16) . . ?
C2 C3 H3 119.1(16) . . ?
C3 C4 C5 118.4(2) . . ?
C3 C4 C7 121.1(2) . . ?
C5 C4 C7 120.5(2) . . ?
C4 C5 C6 121.7(2) . . ?
C4 C5 H5 118.4(16) . . ?
C6 C5 H5 119.9(16) . . ?
C5 C6 C1 120.4(2) . . ?
C5 C6 C8 119.8(2) . . ?
C1 C6 C8 119.7(2) . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
H7B C7 H7A 109.5 . . ?
H7C C7 H7A 109.5 . . ?
N1 C8 N2 110.1(2) . . ?
N1 C8 C6 124.9(2) . . ?
N2 C8 C6 124.8(2) . . ?
C10 C9 N1 108.9(2) . . ?
C10 C9 C11 131.3(2) . . ?
N1 C9 C11 119.7(2) . . ?
C9 C10 N2 106.1(2) . . ?
C9 C10 C17 133.0(2) . . ?
N2 C10 C17 120.6(2) . . ?
C12 C11 C16 118.1(3) . . ?
C12 C11 C9 119.9(2) . . ?
C16 C11 C9 121.9(3) . . ?
C13 C12 C11 121.1(3) . . ?
C13 C12 H12 120.3(19) . . ?
C11 C12 H12 118.5(19) . . ?
C14 C13 C12 120.2(3) . . ?
C14 C13 H13 120.4(19) . . ?
C12 C13 H13 119.3(19) . . ?
C15 C14 C13 119.7(3) . . ?
C15 C14 H14 118(2) . . ?
C13 C14 H14 122(2) . . ?
C14 C15 C16 120.4(3) . . ?
C14 C15 H15 120(2) . . ?
C16 C15 H15 119(2) . . ?
C15 C16 C11 120.3(3) . . ?
C15 C16 H16 121(2) . . ?
C11 C16 H16 118(2) . . ?
C22 C17 C18 119.0(3) . . ?
C22 C17 C10 119.1(2) . . ?
C18 C17 C10 121.9(3) . . ?
C19 C18 C17 120.0(3) . . ?
C19 C18 H18 122.4(19) . . ?
C17 C18 H18 117.6(19) . . ?
C20 C19 C18 120.5(3) . . ?
C20 C19 H19 122(3) . . ?
C18 C19 H19 118(3) . . ?
C21 C20 C19 120.1(3) . . ?
C21 C20 H20 119(2) . . ?
C19 C20 H20 121(2) . . ?
C20 C21 C22 119.8(3) . . ?
C20 C21 H21 120(2) . . ?
C22 C21 H21 120(2) . . ?
C17 C22 C21 120.7(3) . . ?
C17 C22 H22 120.0(19) . . ?
C21 C22 H22 119.3(19) . . ?
C31 C26 C27 120.9(3) . . ?
C31 C26 N2 118.2(2) . . ?
C27 C26 N2 120.9(2) . . ?
C26 C27 C28 118.4(3) . . ?
C26 C27 H27 119.6(18) . . ?
C28 C27 H27 121.7(18) . . ?
C29 C28 C27 120.6(3) . . ?
C29 C28 H28 124(2) . . ?
C27 C28 H28 116(2) . . ?
C28 C29 C30 120.5(3) . . ?
C28 C29 H29 121(2) . . ?
C30 C29 H29 119(2) . . ?
C29 C30 C31 119.6(3) . . ?
C29 C30 H30 119(2) . . ?
C31 C30 H30 122(2) . . ?
C26 C31 C30 120.0(3) . . ?
C26 C31 H31 120.8(19) . . ?
C30 C31 H31 119.1(19) . . ?
N3 C32 N4 106.3(2) . . ?
N3 C32 C2 120.9(2) . . ?
N4 C32 C2 132.6(2) . . ?
C34 C33 N3 106.3(2) . . ?
C34 C33 C35 134.7(2) . . ?
N3 C33 C35 118.9(2) . . ?
C33 C34 N4 106.6(2) . . ?
C33 C34 C41 129.8(2) . . ?
N4 C34 C41 123.4(2) . . ?
C36 C35 C40 119.5(2) . . ?
C36 C35 C33 122.0(2) . . ?
C40 C35 C33 118.5(2) . . ?
C37 C36 C35 119.9(2) . . ?
C37 C36 H36 120.6(18) . . ?
C35 C36 H36 119.5(19) . . ?
C36 C37 C38 120.4(3) . . ?
C36 C37 H37 119.4(19) . . ?
C38 C37 H37 120.2(18) . . ?
C39 C38 C37 120.1(3) . . ?
C39 C38 H38 119(2) . . ?
C37 C38 H38 121(2) . . ?
C38 C39 C40 120.1(3) . . ?
C38 C39 H39 122(2) . . ?
C40 C39 H39 118(2) . . ?
C39 C40 C35 119.9(3) . . ?
C39 C40 H40 118.2(17) . . ?
C35 C40 H40 121.9(17) . . ?
C46 C41 C42 119.4(2) . . ?
C46 C41 C34 118.2(2) . . ?
C42 C41 C34 122.4(2) . . ?
C43 C42 C41 119.7(3) . . ?
C43 C42 H42 120.3(18) . . ?
C41 C42 H42 120.0(18) . . ?
C44 C43 C42 120.6(3) . . ?
C44 C43 H43 120.3(19) . . ?
C42 C43 H43 118.9(19) . . ?
C43 C44 C45 120.2(3) . . ?
C43 C44 H44 119.3(19) . . ?
C45 C44 H44 120.4(19) . . ?
C46 C45 C44 119.6(3) . . ?
C46 C45 H45 119.2(19) . . ?
C44 C45 H45 121.1(19) . . ?
C45 C46 C41 120.5(3) . . ?
C45 C46 H46 120.0(17) . . ?
C41 C46 H46 119.5(17) . . ?
C48 C47 C52 121.8(2) . . ?
C48 C47 N4 119.3(2) . . ?
C52 C47 N4 119.0(2) . . ?
C47 C48 C49 118.9(3) . . ?
C47 C48 H48 122.3(18) . . ?
C49 C48 H48 118.7(18) . . ?
C50 C49 C48 120.2(3) . . ?
C50 C49 H49 123.2(19) . . ?
C48 C49 H49 116.6(19) . . ?
C51 C50 C49 120.3(3) . . ?
C51 C50 H50 118.1(19) . . ?
C49 C50 H50 121.6(19) . . ?
C50 C51 C52 120.2(3) . . ?
C50 C51 H51 120.2(19) . . ?
C52 C51 H51 120(2) . . ?
C47 C52 C51 118.7(3) . . ?
C47 C52 H52 119.5(17) . . ?
C51 C52 H52 121.8(17) . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        27.10
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.513
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.064
####################################################################### 
# 
# 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_FO6011
_database_code_depnum_ccdc_archive 'CCDC 1505094'
_audit_update_record             
;
2018-01-29 deposited with the CCDC.
2018-04-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H32 N4 O4'
_chemical_formula_sum            'C31 H32 N4 O4'
_chemical_formula_weight         524.61

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           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   11.7841(2)
_cell_length_b                   11.7123(2)
_cell_length_c                   20.2881(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.441(1)
_cell_angle_gamma                90
_cell_volume                     2711.67(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    16866
_cell_measurement_theta_min      2.02
_cell_measurement_theta_max      27.54

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.125
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.108
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1112
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6477
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS, Bruker-AXS, 2002'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      133(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  KappaCCD
_diffrn_measurement_method       'phi- + omega-scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16866
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         27.54
_reflns_number_total             6190
_reflns_number_gt                5127
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       COLLECT
_computing_cell_refinement       DENZO
_computing_data_reduction        DENZO
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXL-97

_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)+(0.0446P)²+1.4779P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6190
_refine_ls_number_parameters     474
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1203
_refine_ls_wR_factor_gt          0.1115
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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
O1 O 0.46948(9) 0.41791(9) 0.66847(6) 0.0280(2) Uani 1 1 d . . .
H1O1 H 0.428(2) 0.369(2) 0.6904(12) 0.057(6) Uiso 1 1 d . . .
O2 O 0.93035(9) 0.42238(10) 0.81944(6) 0.0352(3) Uani 1 1 d . . .
O3 O 0.08769(10) 0.80100(11) 0.36594(6) 0.0373(3) Uani 1 1 d . . .
O4 O 0.84552(11) 1.04777(10) 0.43654(7) 0.0394(3) Uani 1 1 d . . .
N1 N 0.51933(12) 0.57451(11) 0.58596(7) 0.0259(3) Uani 1 1 d . . .
H1N1 H 0.4616(18) 0.5330(17) 0.5928(10) 0.044(6) Uiso 1 1 d . . .
N2 N 0.70359(11) 0.62380(10) 0.59713(6) 0.0246(3) Uani 1 1 d . . .
N3 N 0.56180(12) 0.20568(11) 0.83904(7) 0.0249(3) Uani 1 1 d . . .
H1N3 H 0.6336(18) 0.1853(17) 0.8635(10) 0.042(5) Uiso 1 1 d . . .
N4 N 0.42304(11) 0.27944(11) 0.75599(7) 0.0276(3) Uani 1 1 d . . .
C1 C 0.58479(13) 0.41582(12) 0.70341(7) 0.0235(3) Uani 1 1 d . . .
C2 C 0.62295(13) 0.34710(12) 0.76175(8) 0.0234(3) Uani 1 1 d . . .
C3 C 0.73962(13) 0.35084(13) 0.79829(8) 0.0261(3) Uani 1 1 d . . .
H3 H 0.7669(16) 0.3043(15) 0.8385(9) 0.032(5) Uiso 1 1 d . . .
C4 C 0.81879(13) 0.42161(13) 0.77767(8) 0.0268(3) Uani 1 1 d . . .
C5 C 0.78282(13) 0.48587(13) 0.71910(8) 0.0257(3) Uani 1 1 d . . .
H5 H 0.8365(15) 0.5314(15) 0.7036(9) 0.027(4) Uiso 1 1 d . . .
C6 C 0.66586(13) 0.48351(12) 0.68130(7) 0.0236(3) Uani 1 1 d . . .
C7 C 0.63144(13) 0.55773(12) 0.62146(7) 0.0236(3) Uani 1 1 d . . .
C8 C 0.51691(13) 0.65624(12) 0.53670(7) 0.0253(3) Uani 1 1 d . . .
C9 C 0.63252(13) 0.68628(12) 0.54465(7) 0.0246(3) Uani 1 1 d . . .
C10 C 0.68501(13) 0.77782(12) 0.51158(7) 0.0248(3) Uani 1 1 d . . .
C11 C 0.77375(15) 0.75540(14) 0.47970(9) 0.0321(4) Uani 1 1 d . . .
H11 H 0.7996(17) 0.6742(18) 0.4754(10) 0.045(6) Uiso 1 1 d . . .
C12 C 0.82960(15) 0.84240(14) 0.45299(9) 0.0336(4) Uani 1 1 d . . .
H12 H 0.8928(17) 0.8242(16) 0.4331(10) 0.036(5) Uiso 1 1 d . . .
C13 C 0.79518(14) 0.95452(13) 0.45865(8) 0.0296(3) Uani 1 1 d . . .
C14 C 0.70487(15) 0.97885(14) 0.48948(8) 0.0301(3) Uani 1 1 d . . .
H14 H 0.6817(15) 1.0605(16) 0.4938(9) 0.032(5) Uiso 1 1 d . . .
C15 C 0.65065(14) 0.89170(13) 0.51582(8) 0.0279(3) Uani 1 1 d . . .
H15 H 0.5876(15) 0.9082(14) 0.5392(9) 0.025(4) Uiso 1 1 d . . .
C16 C 0.93394(19) 1.02740(18) 0.40114(11) 0.0424(4) Uani 1 1 d . . .
H16C H 0.9990(18) 0.9841(17) 0.4290(10) 0.041(5) Uiso 1 1 d . . .
H16B H 0.9608(19) 1.105(2) 0.3920(11) 0.052(6) Uiso 1 1 d . . .
H16A H 0.899(2) 0.982(2) 0.3583(12) 0.059(7) Uiso 1 1 d . . .
C17 C 0.40696(13) 0.69515(13) 0.49143(8) 0.0264(3) Uani 1 1 d . . .
C18 C 0.40392(14) 0.74635(13) 0.42929(8) 0.0275(3) Uani 1 1 d . . .
H18 H 0.4778(16) 0.7528(15) 0.4141(9) 0.030(4) Uiso 1 1 d . . .
C19 C 0.29916(14) 0.78297(13) 0.38620(8) 0.0272(3) Uani 1 1 d . . .
H19 H 0.2994(15) 0.8187(15) 0.3439(9) 0.028(4) Uiso 1 1 d . . .
C20 C 0.19558(14) 0.76858(13) 0.40480(8) 0.0302(3) Uani 1 1 d . . .
C21 C 0.19672(16) 0.72019(18) 0.46763(11) 0.0457(5) Uani 1 1 d . . .
H21 H 0.120(2) 0.712(2) 0.4816(12) 0.068(7) Uiso 1 1 d . . .
C22 C 0.30093(16) 0.68369(18) 0.50985(10) 0.0425(4) Uani 1 1 d . . .
H22 H 0.302(2) 0.6503(19) 0.5552(12) 0.059(6) Uiso 1 1 d . . .
C23 C 0.08699(16) 0.86011(16) 0.30433(9) 0.0348(4) Uani 1 1 d . . .
H23C H 0.1377(16) 0.9283(16) 0.3148(9) 0.033(5) Uiso 1 1 d . . .
H23B H 0.0043(18) 0.8832(17) 0.2840(10) 0.040(5) Uiso 1 1 d . . .
H23A H 0.1154(16) 0.8114(16) 0.2704(10) 0.037(5) Uiso 1 1 d . . .
C24 C 1.00455(15) 0.51440(16) 0.81094(9) 0.0337(4) Uani 1 1 d . . .
H24C H 1.0281(17) 0.5041(17) 0.7681(11) 0.042(5) Uiso 1 1 d . . .
H24B H 1.0757(18) 0.5056(17) 0.8482(10) 0.041(5) Uiso 1 1 d . . .
H24A H 0.9645(18) 0.5906(19) 0.8123(10) 0.046(6) Uiso 1 1 d . . .
C25 C 0.53756(13) 0.27765(12) 0.78507(8) 0.0238(3) Uani 1 1 d . . .
C26 C 0.45669(14) 0.15917(13) 0.84497(8) 0.0283(3) Uani 1 1 d . A .
C27 C 0.37229(13) 0.20572(13) 0.79334(8) 0.0289(3) Uani 1 1 d . . .
C28 C 0.24172(15) 0.19067(16) 0.77674(11) 0.0379(4) Uani 1 1 d . . .
H28B H 0.2242(18) 0.1187(19) 0.8001(11) 0.049(6) Uiso 1 1 d . . .
H28A H 0.2119(18) 0.1757(18) 0.7269(12) 0.049(6) Uiso 1 1 d . . .
C29 C 0.18116(18) 0.2924(2) 0.79912(15) 0.0561(6) Uani 1 1 d . . .
H29A H 0.200(2) 0.365(2) 0.7720(14) 0.080(8) Uiso 1 1 d . . .
H29B H 0.092(2) 0.284(2) 0.7851(12) 0.065(7) Uiso 1 1 d . . .
H29C H 0.213(3) 0.307(3) 0.8542(17) 0.101(10) Uiso 1 1 d . . .
C30 C 0.45041(16) 0.07472(16) 0.89932(9) 0.0373(4) Uani 1 1 d . . .
H30B H 0.3837 0.0950 0.9186 0.043(9) Uiso 0.638(18) 1 calc PR A 1
H30A H 0.5230 0.0805 0.9364 0.052(10) Uiso 0.638(18) 1 calc PR A 1
H30C H 0.4873 0.1097 0.9439 0.053(18) Uiso 0.362(18) 1 calc PR A 2
H30D H 0.3667 0.0621 0.8979 0.059(19) Uiso 0.362(18) 1 calc PR A 2
C31 C 0.4354(10) -0.0502(3) 0.8740(3) 0.0547(18) Uani 0.638(18) 1 d P A 1
H31A H 0.4320 -0.1007 0.9120 0.082 Uiso 0.638(18) 1 calc PR A 1
H31B H 0.5021 -0.0718 0.8559 0.082 Uiso 0.638(18) 1 calc PR A 1
H31C H 0.3627 -0.0573 0.8381 0.082 Uiso 0.638(18) 1 calc PR A 1
C31A C 0.5011(15) -0.0292(11) 0.8967(8) 0.060(4) Uani 0.362(18) 1 d P A 2
H31D H 0.4912 -0.0764 0.9347 0.090 Uiso 0.362(18) 1 calc PR A 2
H31E H 0.5849 -0.0191 0.8999 0.090 Uiso 0.362(18) 1 calc PR A 2
H31F H 0.4639 -0.0669 0.8536 0.090 Uiso 0.362(18) 1 calc PR 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
O1 C1 1.3672(17) . ?
O1 H1O1 0.94(2) . ?
O2 C4 1.3750(18) . ?
O2 C24 1.425(2) . ?
O3 C20 1.3719(19) . ?
O3 C23 1.427(2) . ?
O4 C13 1.3706(19) . ?
O4 C16 1.425(2) . ?
N1 C7 1.3521(19) . ?
N1 C8 1.3790(19) . ?
N1 H1N1 0.87(2) . ?
N2 C7 1.3322(19) . ?
N2 C9 1.3877(19) . ?
N3 C25 1.3546(19) . ?
N3 C26 1.386(2) . ?
N3 H1N3 0.90(2) . ?
N4 C25 1.3314(19) . ?
N4 C27 1.380(2) . ?
C1 C6 1.399(2) . ?
C1 C2 1.409(2) . ?
C2 C3 1.390(2) . ?
C2 C25 1.461(2) . ?
C3 C4 1.388(2) . ?
C3 H3 0.966(19) . ?
C4 C5 1.381(2) . ?
C5 C6 1.401(2) . ?
C5 H5 0.940(18) . ?
C6 C7 1.466(2) . ?
C8 C9 1.377(2) . ?
C8 C17 1.462(2) . ?
C9 C10 1.480(2) . ?
C10 C11 1.385(2) . ?
C10 C15 1.403(2) . ?
C11 C12 1.394(2) . ?
C11 H11 1.01(2) . ?
C12 C13 1.388(2) . ?
C12 H12 0.957(19) . ?
C13 C14 1.392(2) . ?
C14 C15 1.381(2) . ?
C14 H14 1.004(18) . ?
C15 H15 0.995(17) . ?
C16 H16C 0.97(2) . ?
C16 H16B 1.00(2) . ?
C16 H16A 1.01(2) . ?
C17 C18 1.388(2) . ?
C17 C22 1.397(2) . ?
C18 C19 1.391(2) . ?
C18 H18 0.996(18) . ?
C19 C20 1.375(2) . ?
C19 H19 0.956(18) . ?
C20 C21 1.392(2) . ?
C21 C22 1.378(2) . ?
C21 H21 1.02(3) . ?
C22 H22 1.00(2) . ?
C23 H23C 0.988(19) . ?
C23 H23B 1.00(2) . ?
C23 H23A 1.01(2) . ?
C24 H24C 0.98(2) . ?
C24 H24B 0.98(2) . ?
C24 H24A 1.01(2) . ?
C26 C27 1.365(2) . ?
C26 C30 1.497(2) . ?
C27 C28 1.501(2) . ?
C28 C29 1.515(3) . ?
C28 H28B 1.01(2) . ?
C28 H28A 1.00(2) . ?
C29 H29A 1.07(3) . ?
C29 H29B 1.03(3) . ?
C29 H29C 1.10(3) . ?
C30 C31A 1.363(9) . ?
C30 C31 1.547(5) . ?
C30 H30B 0.9900 . ?
C30 H30A 0.9900 . ?
C30 H30C 0.9900 . ?
C30 H30D 0.9900 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C31A H31D 0.9800 . ?
C31A H31E 0.9800 . ?
C31A H31F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1O1 108.5(14) . . ?
C4 O2 C24 116.84(12) . . ?
C20 O3 C23 116.09(13) . . ?
C13 O4 C16 117.51(14) . . ?
C7 N1 C8 109.13(13) . . ?
C7 N1 H1N1 122.0(13) . . ?
C8 N1 H1N1 128.6(14) . . ?
C7 N2 C9 105.77(12) . . ?
C25 N3 C26 107.58(13) . . ?
C25 N3 H1N3 126.2(13) . . ?
C26 N3 H1N3 125.9(13) . . ?
C25 N4 C27 106.08(13) . . ?
O1 C1 C6 119.57(13) . . ?
O1 C1 C2 120.90(13) . . ?
C6 C1 C2 119.53(13) . . ?
C3 C2 C1 119.72(13) . . ?
C3 C2 C25 120.94(13) . . ?
C1 C2 C25 119.25(13) . . ?
C4 C3 C2 120.51(14) . . ?
C4 C3 H3 118.9(11) . . ?
C2 C3 H3 120.5(11) . . ?
O2 C4 C5 124.61(14) . . ?
O2 C4 C3 115.42(13) . . ?
C5 C4 C3 119.97(14) . . ?
C4 C5 C6 120.63(14) . . ?
C4 C5 H5 120.6(11) . . ?
C6 C5 H5 118.7(11) . . ?
C1 C6 C5 119.54(13) . . ?
C1 C6 C7 122.13(13) . . ?
C5 C6 C7 118.24(13) . . ?
N2 C7 N1 110.33(13) . . ?
N2 C7 C6 125.52(13) . . ?
N1 C7 C6 124.00(13) . . ?
C9 C8 N1 104.56(13) . . ?
C9 C8 C17 133.63(14) . . ?
N1 C8 C17 121.78(13) . . ?
C8 C9 N2 110.20(13) . . ?
C8 C9 C10 130.18(14) . . ?
N2 C9 C10 119.31(13) . . ?
C11 C10 C15 118.15(14) . . ?
C11 C10 C9 121.61(14) . . ?
C15 C10 C9 120.11(14) . . ?
C10 C11 C12 121.85(15) . . ?
C10 C11 H11 119.9(12) . . ?
C12 C11 H11 118.3(12) . . ?
C13 C12 C11 118.92(15) . . ?
C13 C12 H12 121.4(12) . . ?
C11 C12 H12 119.7(12) . . ?
O4 C13 C12 124.59(15) . . ?
O4 C13 C14 115.20(14) . . ?
C12 C13 C14 120.19(15) . . ?
C15 C14 C13 120.14(15) . . ?
C15 C14 H14 120.6(10) . . ?
C13 C14 H14 119.2(10) . . ?
C14 C15 C10 120.72(15) . . ?
C14 C15 H15 120.9(10) . . ?
C10 C15 H15 118.4(10) . . ?
O4 C16 H16C 111.4(12) . . ?
O4 C16 H16B 104.3(13) . . ?
H16C C16 H16B 110.1(17) . . ?
O4 C16 H16A 109.2(13) . . ?
H16C C16 H16A 108.3(17) . . ?
H16B C16 H16A 113.5(18) . . ?
C18 C17 C22 117.53(14) . . ?
C18 C17 C8 121.55(14) . . ?
C22 C17 C8 120.92(14) . . ?
C17 C18 C19 121.45(15) . . ?
C17 C18 H18 119.2(10) . . ?
C19 C18 H18 119.3(10) . . ?
C20 C19 C18 119.95(15) . . ?
C20 C19 H19 120.1(10) . . ?
C18 C19 H19 119.9(10) . . ?
O3 C20 C19 124.55(14) . . ?
O3 C20 C21 115.78(15) . . ?
C19 C20 C21 119.66(15) . . ?
C22 C21 C20 119.92(17) . . ?
C22 C21 H21 120.8(14) . . ?
C20 C21 H21 119.2(14) . . ?
C21 C22 C17 121.45(16) . . ?
C21 C22 H22 120.1(13) . . ?
C17 C22 H22 118.4(13) . . ?
O3 C23 H23C 109.5(11) . . ?
O3 C23 H23B 106.6(11) . . ?
H23C C23 H23B 110.2(16) . . ?
O3 C23 H23A 113.0(11) . . ?
H23C C23 H23A 108.5(15) . . ?
H23B C23 H23A 109.1(15) . . ?
O2 C24 H24C 109.3(12) . . ?
O2 C24 H24B 105.0(12) . . ?
H24C C24 H24B 106.9(16) . . ?
O2 C24 H24A 111.0(12) . . ?
H24C C24 H24A 111.7(16) . . ?
H24B C24 H24A 112.6(16) . . ?
N4 C25 N3 110.73(13) . . ?
N4 C25 C2 123.47(13) . . ?
N3 C25 C2 125.78(13) . . ?
C27 C26 N3 105.81(14) . . ?
C27 C26 C30 131.96(15) . . ?
N3 C26 C30 122.23(15) . . ?
C26 C27 N4 109.80(13) . . ?
C26 C27 C28 129.43(16) . . ?
N4 C27 C28 120.71(15) . . ?
C27 C28 C29 111.92(15) . . ?
C27 C28 H28B 108.0(12) . . ?
C29 C28 H28B 110.4(12) . . ?
C27 C28 H28A 109.2(12) . . ?
C29 C28 H28A 111.6(12) . . ?
H28B C28 H28A 105.4(17) . . ?
C28 C29 H29A 107.2(15) . . ?
C28 C29 H29B 111.6(14) . . ?
H29A C29 H29B 105.6(19) . . ?
C28 C29 H29C 110.8(16) . . ?
H29A C29 H29C 110(2) . . ?
H29B C29 H29C 111(2) . . ?
C31A C30 C26 117.3(3) . . ?
C31A C30 C31 32.5(6) . . ?
C26 C30 C31 113.8(2) . . ?
C31A C30 H30B 129.0 . . ?
C26 C30 H30B 108.8 . . ?
C31 C30 H30B 108.8 . . ?
C31A C30 H30A 77.7 . . ?
C26 C30 H30A 108.8 . . ?
C31 C30 H30A 108.8 . . ?
H30B C30 H30A 107.7 . . ?
C31A C30 H30C 108.0 . . ?
C26 C30 H30C 108.0 . . ?
C31 C30 H30C 133.1 . . ?
H30B C30 H30C 75.5 . . ?
H30A C30 H30C 34.7 . . ?
C31A C30 H30D 108.0 . . ?
C26 C30 H30D 108.0 . . ?
C31 C30 H30D 79.5 . . ?
H30B C30 H30D 33.4 . . ?
H30A C30 H30D 134.2 . . ?
H30C C30 H30D 107.2 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C31A H31D 109.5 . . ?
C30 C31A H31E 109.5 . . ?
H31D C31A H31E 109.5 . . ?
C30 C31A H31F 109.5 . . ?
H31D C31A H31F 109.5 . . ?
H31E C31A H31F 109.5 . . ?

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
O1 H1O1 N4 0.94(2) 1.71(2) 2.5627(17) 150(2) .
N1 H1N1 O1 0.87(2) 2.03(2) 2.6460(17) 126.8(17) .
N3 H1N3 N2 0.90(2) 2.02(2) 2.9077(18) 169.5(19) 2_646
C3 H3 N2 0.966(19) 2.464(19) 3.3634(19) 154.8(14) 2_646
C5 H5 N3 0.940(18) 2.621(18) 3.528(2) 162.5(14) 2_656

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.042
