# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_12mkc1me
_database_code_depnum_ccdc_archive 'CCDC 1412290'
_audit_update_record             
;
2016-04-03 deposited with the CCDC.
2016-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C39 H32 N2 O'
_chemical_formula_sum            'C39 H32 N2 O'
_chemical_formula_weight         544.67

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'
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'
H H 0.0000 0.0000 '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/c'
_symmetry_space_group_name_hall  '-P 2ybc'

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

_cell_length_a                   18.2934(4)
_cell_length_b                   9.6683(2)
_cell_length_c                   18.2645(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.4330(10)
_cell_angle_gamma                90.00
_cell_volume                     2917.31(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    115(2)
_cell_measurement_reflns_used    7592
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      28.283

_exptl_crystal_description       Prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1152
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           ?

_diffrn_ambient_temperature      115(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  'Nonius Kappa Apex II'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13943
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.97
_diffrn_reflns_theta_max         28.30
_reflns_number_total             7201
_reflns_number_gt                5049
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP3 (Farrugia,1997)'
_computing_publication_material  'WinGX publication routines (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)+(0.0836P)²+2.9548P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7201
_refine_ls_number_parameters     347
_refine_ls_number_restraints     0
_refine_ls_number_constraints    12
_refine_ls_R_factor_all          0.1095
_refine_ls_R_factor_gt           0.0757
_refine_ls_wR_factor_ref         0.2088
_refine_ls_wR_factor_gt          0.1832
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.002
_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
C1 C 0.31636(13) 0.2923(2) 0.28918(14) 0.0344(5) Uani 1 1 d . A .
C2 C 0.39243(14) 0.3553(3) 0.35795(15) 0.0386(5) Uani 1 1 d . . .
C3 C 0.45509(13) 0.4065(2) 0.33268(14) 0.0335(5) Uani 1 1 d . . .
C4 C 0.42937(12) 0.4263(2) 0.24549(13) 0.0302(4) Uani 1 1 d . . .
C5 C 0.37289(13) 0.3355(2) 0.18978(14) 0.0333(5) Uani 1 1 d . . .
C6 C 0.33526(14) 0.2269(2) 0.22323(14) 0.0340(5) Uani 1 1 d . . .
H6A H 0.3733 0.1487 0.2461 0.041 Uiso 1 1 calc R . .
H6B H 0.2849 0.1909 0.1792 0.041 Uiso 1 1 calc R . .
C7 C 0.25163(12) 0.4124(2) 0.25927(14) 0.0356(5) Uani 1 1 d . A .
H7 H 0.2792 0.5031 0.2798 0.043 Uiso 1 1 calc R . .
C8 C 0.20094(14) 0.3747(3) 0.30416(16) 0.0448(6) Uani 1 1 d . . .
C9A C 0.13789(18) 0.4735(5) 0.3066(3) 0.0546(11) Uani 0.690(13) 1 d PG A 1
C10A C 0.08762(18) 0.4268(5) 0.3407(3) 0.0546(11) Uani 0.690(13) 1 d PG A 1
H10A H 0.0927 0.3348 0.3606 0.066 Uiso 0.690(13) 1 calc PR A 1
C11A C 0.02991(16) 0.5148(6) 0.3459(3) 0.0546(11) Uani 0.690(13) 1 d PG A 1
H11A H -0.0045 0.4829 0.3692 0.066 Uiso 0.690(13) 1 calc PR A 1
C12A C 0.02247(15) 0.6495(6) 0.3168(3) 0.0546(11) Uani 0.690(13) 1 d PG A 1
H12A H -0.0170 0.7096 0.3204 0.066 Uiso 0.690(13) 1 calc PR A 1
C13A C 0.07274(16) 0.6961(5) 0.2827(3) 0.0546(11) Uani 0.690(13) 1 d PG A 1
H13A H 0.0677 0.7881 0.2628 0.066 Uiso 0.690(13) 1 calc PR A 1
C14A C 0.13046(18) 0.6081(5) 0.2775(3) 0.0546(11) Uani 0.690(13) 1 d PG A 1
H14A H 0.1648 0.6400 0.2542 0.066 Uiso 0.690(13) 1 calc PR A 1
C9B C 0.1396(4) 0.4451(8) 0.3162(6) 0.0469(15) Uiso 0.310(13) 1 d PG A 2
C10B C 0.0990(5) 0.3851(6) 0.3572(5) 0.0469(15) Uiso 0.310(13) 1 d PG A 2
H10B H 0.1109 0.2927 0.3764 0.056 Uiso 0.310(13) 1 calc PR A 2
C11B C 0.0408(5) 0.4602(10) 0.3703(5) 0.0469(15) Uiso 0.310(13) 1 d PG A 2
H11B H 0.0130 0.4191 0.3983 0.056 Uiso 0.310(13) 1 calc PR A 2
C12B C 0.0233(4) 0.5954(10) 0.3422(5) 0.0469(15) Uiso 0.310(13) 1 d PG A 2
H12B H -0.0164 0.6467 0.3511 0.056 Uiso 0.310(13) 1 calc PR A 2
C13B C 0.0640(6) 0.6554(6) 0.3011(4) 0.0469(15) Uiso 0.310(13) 1 d PG A 2
H13B H 0.0520 0.7478 0.2820 0.056 Uiso 0.310(13) 1 calc PR A 2
C14B C 0.1221(6) 0.5803(8) 0.2881(5) 0.0469(15) Uiso 0.310(13) 1 d PG A 2
H14B H 0.1499 0.6214 0.2601 0.056 Uiso 0.310(13) 1 calc PR A 2
C15 C 0.19973(13) 0.4224(2) 0.16880(15) 0.0373(5) Uani 1 1 d . . .
C16 C 0.14294(14) 0.3207(3) 0.12791(16) 0.0450(6) Uani 1 1 d . A .
H16 H 0.1369 0.2431 0.1568 0.054 Uiso 1 1 calc R . .
C17 C 0.09507(16) 0.3321(3) 0.04499(18) 0.0547(7) Uani 1 1 d . . .
H17 H 0.0569 0.2615 0.0179 0.066 Uiso 1 1 calc R A .
C18 C 0.10174(17) 0.4445(3) 0.00079(18) 0.0560(7) Uani 1 1 d . A .
C19 C 0.15886(18) 0.5450(3) 0.04194(18) 0.0530(7) Uani 1 1 d . . .
H19 H 0.1649 0.6226 0.0131 0.064 Uiso 1 1 calc R A .
C20 C 0.20705(15) 0.5342(3) 0.12421(17) 0.0454(6) Uani 1 1 d . A .
H20 H 0.2459 0.6042 0.1509 0.055 Uiso 1 1 calc R . .
C21 C 0.0490(2) 0.4572(5) -0.08932(19) 0.0778(11) Uani 1 1 d . . .
H21A H 0.0356 0.5547 -0.1034 0.117 Uiso 1 1 calc R A .
H21B H -0.0010 0.4042 -0.1036 0.117 Uiso 1 1 calc R . .
H21C H 0.0781 0.4208 -0.1194 0.117 Uiso 1 1 calc R . .
C22 C 0.25096(17) -0.0324(3) 0.36228(17) 0.0537(7) Uani 1 1 d . . .
H22 H 0.1964 -0.0063 0.3478 0.064 Uiso 1 1 calc R . .
C23 C 0.2774(2) -0.1639(4) 0.39146(18) 0.0629(8) Uani 1 1 d . . .
H23 H 0.2410 -0.2267 0.3985 0.075 Uiso 1 1 calc R . .
C24 C 0.3557(2) -0.2058(3) 0.41062(18) 0.0597(8) Uani 1 1 d . . .
H24 H 0.3722 -0.2979 0.4281 0.072 Uiso 1 1 calc R . .
C25 C 0.41002(18) -0.1118(3) 0.40405(16) 0.0497(6) Uani 1 1 d . . .
H25 H 0.4643 -0.1391 0.4179 0.060 Uiso 1 1 calc R . .
C26 C 0.38533(16) 0.0215(3) 0.37742(15) 0.0434(6) Uani 1 1 d . . .
H26 H 0.4233 0.0862 0.3749 0.052 Uiso 1 1 calc R . .
C27 C 0.30503(16) 0.0619(3) 0.35417(15) 0.0441(6) Uani 1 1 d . A .
C28 C 0.34986(14) 0.3495(3) 0.10746(15) 0.0398(5) Uani 1 1 d . . .
H28 H 0.3144 0.2836 0.0707 0.048 Uiso 1 1 calc R . .
C29 C 0.37847(15) 0.4595(3) 0.07855(16) 0.0445(6) Uani 1 1 d . . .
H29 H 0.3632 0.4685 0.0221 0.053 Uiso 1 1 calc R . .
C30 C 0.42917(15) 0.5559(3) 0.13197(16) 0.0432(6) Uani 1 1 d . . .
H30 H 0.4461 0.6341 0.1118 0.052 Uiso 1 1 calc R . .
C31 C 0.45546(13) 0.5399(2) 0.21450(15) 0.0367(5) Uani 1 1 d . . .
H31 H 0.4914 0.6059 0.2507 0.044 Uiso 1 1 calc R . .
C32 C 0.53088(13) 0.4212(2) 0.39198(14) 0.0363(5) Uani 1 1 d . . .
H32 H 0.5344 0.4266 0.4453 0.044 Uiso 1 1 calc R . .
C33 C 0.60899(13) 0.4302(2) 0.38674(15) 0.0360(5) Uani 1 1 d . . .
C34 C 0.67757(14) 0.4759(3) 0.45569(15) 0.0407(5) Uani 1 1 d . . .
H34 H 0.6717 0.5099 0.5017 0.049 Uiso 1 1 calc R . .
C35 C 0.75344(14) 0.4709(3) 0.45602(16) 0.0437(6) Uani 1 1 d . . .
H35 H 0.7992 0.5024 0.5025 0.052 Uiso 1 1 calc R . .
C36 C 0.76413(14) 0.4211(3) 0.39023(16) 0.0413(5) Uani 1 1 d . . .
C37 C 0.69713(14) 0.3765(2) 0.32334(16) 0.0388(5) Uani 1 1 d . . .
H37 H 0.7035 0.3423 0.2777 0.047 Uiso 1 1 calc R . .
C38 C 0.62116(14) 0.3803(2) 0.32126(14) 0.0357(5) Uani 1 1 d . . .
H38 H 0.5761 0.3484 0.2743 0.043 Uiso 1 1 calc R . .
C39 C 0.84771(16) 0.4187(3) 0.3913(2) 0.0548(7) Uani 1 1 d . . .
H39A H 0.8849 0.4757 0.4362 0.082 Uiso 1 1 calc R . .
H39B H 0.8444 0.4555 0.3399 0.082 Uiso 1 1 calc R . .
H39C H 0.8677 0.3233 0.3983 0.082 Uiso 1 1 calc R . .
N1 N 0.21495(13) 0.2520(3) 0.33488(15) 0.0521(6) Uani 1 1 d . A .
N2 N 0.27724(13) 0.1930(2) 0.32249(15) 0.0484(6) Uani 1 1 d . . .
O1 O 0.39887(11) 0.3607(2) 0.42697(11) 0.0524(5) 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
C1 N2 1.476(3) . ?
C1 C6 1.526(3) . ?
C1 C2 1.544(3) . ?
C1 C7 1.579(3) . ?
C2 O1 1.216(3) . ?
C2 C3 1.492(3) . ?
C3 C32 1.351(3) . ?
C3 C4 1.466(3) . ?
C4 C5 1.404(3) . ?
C4 C31 1.409(3) . ?
C5 C28 1.383(3) . ?
C5 C6 1.520(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C15 1.514(3) . ?
C7 C8 1.523(3) . ?
C7 H7 1.0000 . ?
C8 N1 1.290(4) . ?
C8 C9B 1.408(6) . ?
C8 C9A 1.513(4) . ?
C9A C10A 1.3900 . ?
C9A C14A 1.3900 . ?
C10A C11A 1.3900 . ?
C10A H10A 0.9500 . ?
C11A C12A 1.3900 . ?
C11A H11A 0.9500 . ?
C12A C13A 1.3900 . ?
C12A H12A 0.9500 . ?
C13A C14A 1.3900 . ?
C13A H13A 0.9500 . ?
C14A H14A 0.9500 . ?
C9B C10B 1.3900 . ?
C9B C14B 1.3900 . ?
C10B C11B 1.3900 . ?
C10B H10B 0.9500 . ?
C11B C12B 1.3900 . ?
C11B H11B 0.9500 . ?
C12B C13B 1.3900 . ?
C12B H12B 0.9500 . ?
C13B C14B 1.3900 . ?
C13B H13B 0.9500 . ?
C14B H14B 0.9500 . ?
C15 C16 1.392(3) . ?
C15 C20 1.394(4) . ?
C16 C17 1.391(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.390(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.388(4) . ?
C18 C21 1.514(4) . ?
C19 C20 1.381(4) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.383(5) . ?
C22 C27 1.399(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.381(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.390(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.383(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.398(4) . ?
C26 H26 0.9500 . ?
C27 N2 1.395(4) . ?
C28 C29 1.386(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.380(4) . ?
C29 H29 0.9500 . ?
C30 C31 1.380(3) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 C33 1.475(3) . ?
C32 H32 0.9500 . ?
C33 C38 1.393(3) . ?
C33 C34 1.413(3) . ?
C34 C35 1.386(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.384(4) . ?
C35 H35 0.9500 . ?
C36 C37 1.377(4) . ?
C36 C39 1.521(3) . ?
C37 C38 1.374(3) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
N1 N2 1.377(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

N2 C1 C6 111.72(19) . . ?
N2 C1 C2 110.4(2) . . ?
C6 C1 C2 112.03(17) . . ?
N2 C1 C7 101.36(16) . . ?
C6 C1 C7 114.97(19) . . ?
C2 C1 C7 105.73(18) . . ?
O1 C2 C3 124.1(2) . . ?
O1 C2 C1 120.8(2) . . ?
C3 C2 C1 115.01(19) . . ?
C32 C3 C4 126.7(2) . . ?
C32 C3 C2 116.6(2) . . ?
C4 C3 C2 116.65(19) . . ?
C5 C4 C31 117.8(2) . . ?
C5 C4 C3 119.89(19) . . ?
C31 C4 C3 122.1(2) . . ?
C28 C5 C4 120.9(2) . . ?
C28 C5 C6 121.7(2) . . ?
C4 C5 C6 117.4(2) . . ?
C5 C6 C1 109.05(18) . . ?
C5 C6 H6A 109.9 . . ?
C1 C6 H6A 109.9 . . ?
C5 C6 H6B 109.9 . . ?
C1 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
C15 C7 C8 111.18(18) . . ?
C15 C7 C1 116.74(18) . . ?
C8 C7 C1 100.20(19) . . ?
C15 C7 H7 109.4 . . ?
C8 C7 H7 109.4 . . ?
C1 C7 H7 109.4 . . ?
N1 C8 C9B 113.6(4) . . ?
N1 C8 C9A 125.4(3) . . ?
N1 C8 C7 113.7(2) . . ?
C9B C8 C7 132.7(4) . . ?
C9A C8 C7 120.8(3) . . ?
C10A C9A C14A 120.0 . . ?
C10A C9A C8 117.9(3) . . ?
C14A C9A C8 122.1(3) . . ?
C9A C10A C11A 120.0 . . ?
C9A C10A H10A 120.0 . . ?
C11A C10A H10A 120.0 . . ?
C12A C11A C10A 120.0 . . ?
C12A C11A H11A 120.0 . . ?
C10A C11A H11A 120.0 . . ?
C13A C12A C11A 120.0 . . ?
C13A C12A H12A 120.0 . . ?
C11A C12A H12A 120.0 . . ?
C12A C13A C14A 120.0 . . ?
C12A C13A H13A 120.0 . . ?
C14A C13A H13A 120.0 . . ?
C13A C14A C9A 120.0 . . ?
C13A C14A H14A 120.0 . . ?
C9A C14A H14A 120.0 . . ?
C10B C9B C14B 120.0 . . ?
C10B C9B C8 121.9(6) . . ?
C14B C9B C8 118.0(6) . . ?
C11B C10B C9B 120.0 . . ?
C11B C10B H10B 120.0 . . ?
C9B C10B H10B 120.0 . . ?
C10B C11B C12B 120.0 . . ?
C10B C11B H11B 120.0 . . ?
C12B C11B H11B 120.0 . . ?
C13B C12B C11B 120.0 . . ?
C13B C12B H12B 120.0 . . ?
C11B C12B H12B 120.0 . . ?
C12B C13B C14B 120.0 . . ?
C12B C13B H13B 120.0 . . ?
C14B C13B H13B 120.0 . . ?
C13B C14B C9B 120.0 . . ?
C13B C14B H14B 120.0 . . ?
C9B C14B H14B 120.0 . . ?
C16 C15 C20 118.1(2) . . ?
C16 C15 C7 120.9(2) . . ?
C20 C15 C7 121.0(2) . . ?
C17 C16 C15 120.2(3) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C18 C17 C16 121.6(3) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C19 C18 C17 117.8(3) . . ?
C19 C18 C21 120.8(3) . . ?
C17 C18 C21 121.4(3) . . ?
C20 C19 C18 121.1(3) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C19 C20 C15 121.2(3) . . ?
C19 C20 H20 119.4 . . ?
C15 C20 H20 119.4 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C27 119.6(3) . . ?
C23 C22 H22 120.2 . . ?
C27 C22 H22 120.2 . . ?
C24 C23 C22 121.4(3) . . ?
C24 C23 H23 119.3 . . ?
C22 C23 H23 119.3 . . ?
C23 C24 C25 119.2(3) . . ?
C23 C24 H24 120.4 . . ?
C25 C24 H24 120.4 . . ?
C26 C25 C24 120.2(3) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C25 C26 C27 120.6(2) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?
N2 C27 C26 121.8(2) . . ?
N2 C27 C22 119.2(2) . . ?
C26 C27 C22 119.0(3) . . ?
C5 C28 C29 120.0(2) . . ?
C5 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
C30 C29 C28 119.9(2) . . ?
C30 C29 H29 120.1 . . ?
C28 C29 H29 120.1 . . ?
C29 C30 C31 120.6(2) . . ?
C29 C30 H30 119.7 . . ?
C31 C30 H30 119.7 . . ?
C30 C31 C4 120.4(2) . . ?
C30 C31 H31 119.8 . . ?
C4 C31 H31 119.8 . . ?
C3 C32 C33 130.0(2) . . ?
C3 C32 H32 115.0 . . ?
C33 C32 H32 115.0 . . ?
C38 C33 C34 117.7(2) . . ?
C38 C33 C32 123.5(2) . . ?
C34 C33 C32 118.3(2) . . ?
C35 C34 C33 119.8(2) . . ?
C35 C34 H34 120.1 . . ?
C33 C34 H34 120.1 . . ?
C36 C35 C34 121.5(2) . . ?
C36 C35 H35 119.2 . . ?
C34 C35 H35 119.2 . . ?
C37 C36 C35 118.4(2) . . ?
C37 C36 C39 120.9(2) . . ?
C35 C36 C39 120.7(2) . . ?
C38 C37 C36 121.4(2) . . ?
C38 C37 H37 119.3 . . ?
C36 C37 H37 119.3 . . ?
C37 C38 C33 121.2(2) . . ?
C37 C38 H38 119.4 . . ?
C33 C38 H38 119.4 . . ?
C36 C39 H39A 109.5 . . ?
C36 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C36 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C8 N1 N2 109.5(2) . . ?
N1 N2 C27 119.2(2) . . ?
N1 N2 C1 112.3(2) . . ?
C27 N2 C1 127.39(19) . . ?


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
N2 C1 C2 O1 -24.9(3) . . . . ?
C6 C1 C2 O1 -150.1(2) . . . . ?
C7 C1 C2 O1 83.9(3) . . . . ?
N2 C1 C2 C3 154.82(19) . . . . ?
C6 C1 C2 C3 29.6(3) . . . . ?
C7 C1 C2 C3 -96.3(2) . . . . ?
O1 C2 C3 C32 19.9(4) . . . . ?
C1 C2 C3 C32 -159.8(2) . . . . ?
O1 C2 C3 C4 -164.2(2) . . . . ?
C1 C2 C3 C4 16.1(3) . . . . ?
C32 C3 C4 C5 139.9(2) . . . . ?
C2 C3 C4 C5 -35.5(3) . . . . ?
C32 C3 C4 C31 -44.4(3) . . . . ?
C2 C3 C4 C31 140.2(2) . . . . ?
C31 C4 C5 C28 6.3(3) . . . . ?
C3 C4 C5 C28 -177.8(2) . . . . ?
C31 C4 C5 C6 -170.65(19) . . . . ?
C3 C4 C5 C6 5.3(3) . . . . ?
C28 C5 C6 C1 -136.2(2) . . . . ?
C4 C5 C6 C1 40.8(3) . . . . ?
N2 C1 C6 C5 178.23(19) . . . . ?
C2 C1 C6 C5 -57.3(2) . . . . ?
C7 C1 C6 C5 63.4(2) . . . . ?
N2 C1 C7 C15 -104.2(2) . . . . ?
C6 C1 C7 C15 16.5(3) . . . . ?
C2 C1 C7 C15 140.6(2) . . . . ?
N2 C1 C7 C8 15.9(2) . . . . ?
C6 C1 C7 C8 136.57(19) . . . . ?
C2 C1 C7 C8 -99.3(2) . . . . ?
C15 C7 C8 N1 110.7(3) . . . . ?
C1 C7 C8 N1 -13.3(3) . . . . ?
C15 C7 C8 C9B -66.4(6) . . . . ?
C1 C7 C8 C9B 169.5(6) . . . . ?
C15 C7 C8 C9A -66.3(3) . . . . ?
C1 C7 C8 C9A 169.7(3) . . . . ?
N1 C8 C9A C10A -3.6(4) . . . . ?
C9B C8 C9A C10A -8(2) . . . . ?
C7 C8 C9A C10A 173.0(2) . . . . ?
N1 C8 C9A C14A 175.0(2) . . . . ?
C9B C8 C9A C14A 171(3) . . . . ?
C7 C8 C9A C14A -8.4(4) . . . . ?
C14A C9A C10A C11A 0.0 . . . . ?
C8 C9A C10A C11A 178.6(3) . . . . ?
C9A C10A C11A C12A 0.0 . . . . ?
C10A C11A C12A C13A 0.0 . . . . ?
C11A C12A C13A C14A 0.0 . . . . ?
C12A C13A C14A C9A 0.0 . . . . ?
C10A C9A C14A C13A 0.0 . . . . ?
C8 C9A C14A C13A -178.6(3) . . . . ?
N1 C8 C9B C10B -0.2(7) . . . . ?
C9A C8 C9B C10B 176(3) . . . . ?
C7 C8 C9B C10B 176.9(4) . . . . ?
N1 C8 C9B C14B 177.5(3) . . . . ?
C9A C8 C9B C14B -6(2) . . . . ?
C7 C8 C9B C14B -5.3(8) . . . . ?
C14B C9B C10B C11B 0.0 . . . . ?
C8 C9B C10B C11B 177.7(8) . . . . ?
C9B C10B C11B C12B 0.0 . . . . ?
C10B C11B C12B C13B 0.0 . . . . ?
C11B C12B C13B C14B 0.0 . . . . ?
C12B C13B C14B C9B 0.0 . . . . ?
C10B C9B C14B C13B 0.0 . . . . ?
C8 C9B C14B C13B -177.8(7) . . . . ?
C8 C7 C15 C16 -46.3(3) . . . . ?
C1 C7 C15 C16 67.8(3) . . . . ?
C8 C7 C15 C20 133.3(2) . . . . ?
C1 C7 C15 C20 -112.7(2) . . . . ?
C20 C15 C16 C17 -0.3(4) . . . . ?
C7 C15 C16 C17 179.2(2) . . . . ?
C15 C16 C17 C18 -0.5(4) . . . . ?
C16 C17 C18 C19 0.9(4) . . . . ?
C16 C17 C18 C21 -179.4(3) . . . . ?
C17 C18 C19 C20 -0.5(4) . . . . ?
C21 C18 C19 C20 179.8(3) . . . . ?
C18 C19 C20 C15 -0.3(4) . . . . ?
C16 C15 C20 C19 0.7(3) . . . . ?
C7 C15 C20 C19 -178.8(2) . . . . ?
C27 C22 C23 C24 -1.9(5) . . . . ?
C22 C23 C24 C25 3.1(5) . . . . ?
C23 C24 C25 C26 -1.0(4) . . . . ?
C24 C25 C26 C27 -2.2(4) . . . . ?
C25 C26 C27 N2 -176.1(2) . . . . ?
C25 C26 C27 C22 3.3(4) . . . . ?
C23 C22 C27 N2 178.2(3) . . . . ?
C23 C22 C27 C26 -1.3(4) . . . . ?
C4 C5 C28 C29 -4.3(3) . . . . ?
C6 C5 C28 C29 172.5(2) . . . . ?
C5 C28 C29 C30 -0.8(4) . . . . ?
C28 C29 C30 C31 3.7(4) . . . . ?
C29 C30 C31 C4 -1.5(3) . . . . ?
C5 C4 C31 C30 -3.4(3) . . . . ?
C3 C4 C31 C30 -179.2(2) . . . . ?
C4 C3 C32 C33 -14.7(4) . . . . ?
C2 C3 C32 C33 160.7(2) . . . . ?
C3 C32 C33 C38 -22.0(4) . . . . ?
C3 C32 C33 C34 166.2(2) . . . . ?
C38 C33 C34 C35 0.5(4) . . . . ?
C32 C33 C34 C35 172.8(2) . . . . ?
C33 C34 C35 C36 -0.4(4) . . . . ?
C34 C35 C36 C37 0.3(4) . . . . ?
C34 C35 C36 C39 179.0(2) . . . . ?
C35 C36 C37 C38 -0.2(4) . . . . ?
C39 C36 C37 C38 -178.9(2) . . . . ?
C36 C37 C38 C33 0.3(4) . . . . ?
C34 C33 C38 C37 -0.4(3) . . . . ?
C32 C33 C38 C37 -172.3(2) . . . . ?
C9B C8 N1 N2 -178.1(5) . . . . ?
C9A C8 N1 N2 -179.0(3) . . . . ?
C7 C8 N1 N2 4.2(3) . . . . ?
C8 N1 N2 C27 177.1(2) . . . . ?
C8 N1 N2 C1 8.1(3) . . . . ?
C26 C27 N2 N1 -150.3(2) . . . . ?
C22 C27 N2 N1 30.3(4) . . . . ?
C26 C27 N2 C1 16.9(4) . . . . ?
C22 C27 N2 C1 -162.5(2) . . . . ?
C6 C1 N2 N1 -138.6(2) . . . . ?
C2 C1 N2 N1 96.0(2) . . . . ?
C7 C1 N2 N1 -15.7(3) . . . . ?
C6 C1 N2 C27 53.5(3) . . . . ?
C2 C1 N2 C27 -71.9(3) . . . . ?
C7 C1 N2 C27 176.4(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        28.30
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.637
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_2904
_database_code_depnum_ccdc_archive 'CCDC 1471593'
_audit_update_record             
;
2016-03-31 deposited with the CCDC.
2016-05-09 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT601_2904                
;
PROBLEM: Structure Contains Solvent Accessible VOIDS of .        379 Ang3
RESPONSE: Disordered solvent was masked, only crystals of low quality 
;
_vrf_PLAT230_2904                
;
PROBLEM: Hirshfeld Test Diff for    O3     --  C43     ..       12.7 s.u.
RESPONSE: low crystal quality, hence the relatively bad data
;
_vrf_PLAT230_2904_2              
;
PROBLEM: Hirshfeld Test Diff for    C42    --  C43     ..        7.4 s.u.
RESPONSE: low crystal quality, hence the relatively bad data
;
_vrf_PLAT230_2904_3              
;
PROBLEM: Hirshfeld Test Diff for    C43    --  C44     ..        7.5 s.u.
RESPONSE: low crystal quality, hence the relatively bad data
;
_vrf_PLAT026_2904                
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..         49 %
RESPONSE: low crystal quality, hence the relatively bad data
;
# Added during the CSD deposition process: Thursday 31 March 2016 10:21 AM
# end Validation Reply Form

_audit_creation_date             2016-03-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
4,4''-bis(4-methoxyphenyl)-2,2'',5,5''-tetraphenyl-2,2'',4,4''-tetrahydro-2'H,4'H-dispiro[pyrazole-3,1'-naphthalene-3',3''-pyrazol]-2'-one
_chemical_formula_moiety         'C52 H42 N4 O3'
_chemical_formula_sum            'C52 H42 N4 O3'
_chemical_formula_weight         770.89
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   14.5227(14)
_cell_length_b                   21.1915(17)
_cell_length_c                   15.1214(15)
_cell_angle_alpha                90
_cell_angle_beta                 104.682(9)
_cell_angle_gamma                90
_cell_volume                     4501.8(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2857
_cell_measurement_temperature    173
_cell_measurement_theta_max      22.8450
_cell_measurement_theta_min      2.4090
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94727
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1624
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.1215
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7909
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.250
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 16.0560
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3888
_reflns_number_total             7909
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     534
_refine_ls_number_reflns         7909
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1387
_refine_ls_R_factor_gt           0.0736
_refine_ls_restrained_S_all      0.951
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0818P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1653
_refine_ls_wR_factor_ref         0.1906
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C18(H18), C38(H38)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C20(H20), C21(H21), C23(H23), C24(H24), C27(H27), C28(H28), C29(H29),
  C30(H30), C31(H31), C33(H33), C34(H34), C35(H35), C36(H36), C37(H37),
 C41(H41), C42(H42), C44(H44), C45(H45), C48(H48), C49(H49), C50(H50), C51(H51),
  C52(H52)
2.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C46(H46A,H46B,H46C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.22104(17) 0.22611(11) 0.74898(16) 0.0419(6) Uani 1 1 d . . . . .
O2 O 0.24239(18) -0.14350(11) 0.50917(17) 0.0527(7) Uani 1 1 d . . . . .
O3 O 0.0230(3) 0.17512(16) 0.1750(2) 0.0914(11) Uani 1 1 d . . . . .
N1 N 0.28874(18) 0.11152(13) 0.81800(19) 0.0340(7) Uani 1 1 d . . . . .
N2 N 0.38197(19) 0.12051(12) 0.8136(2) 0.0347(7) Uani 1 1 d . . . . .
N3 N 0.02989(19) 0.23297(13) 0.63537(19) 0.0347(7) Uani 1 1 d . . . . .
N4 N 0.0500(2) 0.29605(13) 0.62358(19) 0.0368(7) Uani 1 1 d . . . . .
C1 C 0.1847(2) 0.18165(16) 0.7033(2) 0.0313(8) Uani 1 1 d . . . . .
C2 C 0.2230(2) 0.11433(15) 0.7270(2) 0.0313(8) Uani 1 1 d . . . . .
C3 C 0.1409(2) 0.06676(16) 0.7109(2) 0.0320(8) Uani 1 1 d . . . . .
C4 C 0.1410(3) 0.01620(18) 0.7687(3) 0.0466(10) Uani 1 1 d . . . . .
H4 H 0.1902 0.0123 0.8234 0.056 Uiso 1 1 calc R . . . .
C5 C 0.0695(3) -0.02873(19) 0.7470(3) 0.0614(12) Uani 1 1 d . . . . .
H5 H 0.0696 -0.0635 0.7867 0.074 Uiso 1 1 calc R . . . .
C6 C -0.0015(3) -0.02281(19) 0.6675(3) 0.0506(11) Uani 1 1 d . . . . .
H6 H -0.0499 -0.0540 0.6518 0.061 Uiso 1 1 calc R . . . .
C7 C -0.0030(2) 0.02801(17) 0.6105(2) 0.0379(9) Uani 1 1 d . . . . .
H7 H -0.0527 0.0318 0.5561 0.046 Uiso 1 1 calc R . . . .
C8 C 0.0678(2) 0.07395(16) 0.6319(2) 0.0330(8) Uani 1 1 d . . . . .
C9 C 0.0681(2) 0.12836(16) 0.5693(2) 0.0339(8) Uani 1 1 d . . . . .
H9A H 0.0022 0.1350 0.5321 0.041 Uiso 1 1 calc R . . . .
H9B H 0.1072 0.1167 0.5269 0.041 Uiso 1 1 calc R . . . .
C10 C 0.1054(2) 0.19100(15) 0.6150(2) 0.0311(8) Uani 1 1 d . . . . .
C11 C 0.2676(2) 0.13076(15) 0.9004(2) 0.0322(8) Uani 1 1 d . . . . .
C12 C 0.3404(3) 0.13902(15) 0.9791(2) 0.0349(9) Uani 1 1 d . . . . .
H12 H 0.4048 0.1348 0.9764 0.042 Uiso 1 1 calc R . . . .
C13 C 0.3201(3) 0.15342(16) 1.0617(3) 0.0410(9) Uani 1 1 d . . . . .
H13 H 0.3707 0.1591 1.1149 0.049 Uiso 1 1 calc R . . . .
C14 C 0.2272(3) 0.1595(2) 1.0670(3) 0.0531(11) Uani 1 1 d . . . . .
H14 H 0.2133 0.1691 1.1236 0.064 Uiso 1 1 calc R . . . .
C15 C 0.1543(3) 0.15148(18) 0.9886(3) 0.0483(10) Uani 1 1 d . . . . .
H15 H 0.0901 0.1559 0.9916 0.058 Uiso 1 1 calc R . . . .
C16 C 0.1736(3) 0.13717(17) 0.9061(2) 0.0413(9) Uani 1 1 d . . . . .
H16 H 0.1228 0.1317 0.8530 0.050 Uiso 1 1 calc R . . . .
C17 C 0.3871(2) 0.11609(15) 0.7296(3) 0.0343(8) Uani 1 1 d . . . . .
C18 C 0.2936(2) 0.10119(15) 0.6635(2) 0.0342(8) Uani 1 1 d . . . . .
H18 H 0.2812 0.1327 0.6126 0.041 Uiso 1 1 calc R . . . .
C19 C 0.2882(2) 0.03552(16) 0.6238(2) 0.0337(8) Uani 1 1 d . . . . .
C20 C 0.2587(2) 0.02517(16) 0.5300(2) 0.0364(9) Uani 1 1 d . . . . .
H20 H 0.2456 0.0604 0.4898 0.044 Uiso 1 1 calc R . . . .
C21 C 0.2480(2) -0.03470(17) 0.4941(2) 0.0371(9) Uani 1 1 d . . . . .
H21 H 0.2299 -0.0406 0.4298 0.045 Uiso 1 1 calc R . . . .
C22 C 0.2637(2) -0.08648(16) 0.5520(3) 0.0399(9) Uani 1 1 d . . . . .
C23 C 0.2972(3) -0.07816(16) 0.6451(3) 0.0447(10) Uani 1 1 d . . . . .
H23 H 0.3115 -0.1135 0.6849 0.054 Uiso 1 1 calc R . . . .
C24 C 0.3098(3) -0.01714(17) 0.6798(2) 0.0422(9) Uani 1 1 d . . . . .
H24 H 0.3339 -0.0113 0.7438 0.051 Uiso 1 1 calc R . . . .
C25 C 0.2442(3) -0.19743(18) 0.5663(3) 0.0631(12) Uani 1 1 d . . . . .
H25A H 0.2214 -0.2345 0.5281 0.095 Uiso 1 1 calc GR . . . .
H25B H 0.2028 -0.1899 0.6073 0.095 Uiso 1 1 calc GR . . . .
H25C H 0.3094 -0.2049 0.6025 0.095 Uiso 1 1 calc GR . . . .
C26 C 0.4764(2) 0.12552(16) 0.7043(2) 0.0373(9) Uani 1 1 d . . . . .
C27 C 0.4790(3) 0.12517(18) 0.6125(3) 0.0468(10) Uani 1 1 d . . . . .
H27 H 0.4230 0.1158 0.5663 0.056 Uiso 1 1 calc R . . . .
C28 C 0.5637(3) 0.1386(2) 0.5886(3) 0.0545(11) Uani 1 1 d . . . . .
H28 H 0.5651 0.1377 0.5261 0.065 Uiso 1 1 calc R . . . .
C29 C 0.6454(3) 0.15304(19) 0.6548(3) 0.0567(12) Uani 1 1 d . . . . .
H29 H 0.7025 0.1632 0.6383 0.068 Uiso 1 1 calc R . . . .
C30 C 0.6428(3) 0.15256(19) 0.7460(3) 0.0535(11) Uani 1 1 d . . . . .
H30 H 0.6990 0.1617 0.7921 0.064 Uiso 1 1 calc R . . . .
C31 C 0.5594(3) 0.13888(17) 0.7707(3) 0.0469(10) Uani 1 1 d . . . . .
H31 H 0.5590 0.1386 0.8334 0.056 Uiso 1 1 calc R . . . .
C32 C -0.0121(2) 0.22077(18) 0.7096(2) 0.0380(9) Uani 1 1 d . . . . .
C33 C -0.0653(2) 0.16670(18) 0.7090(3) 0.0439(10) Uani 1 1 d . . . . .
H33 H -0.0746 0.1383 0.6589 0.053 Uiso 1 1 calc R . . . .
C34 C -0.1048(3) 0.1537(2) 0.7805(3) 0.0523(11) Uani 1 1 d . . . . .
H34 H -0.1380 0.1152 0.7814 0.063 Uiso 1 1 calc R . . . .
C35 C -0.0963(3) 0.1964(2) 0.8508(3) 0.0581(12) Uani 1 1 d . . . . .
H35 H -0.1249 0.1879 0.8995 0.070 Uiso 1 1 calc R . . . .
C36 C -0.0462(3) 0.2514(2) 0.8502(3) 0.0608(12) Uani 1 1 d . . . . .
H36 H -0.0409 0.2810 0.8984 0.073 Uiso 1 1 calc R . . . .
C37 C -0.0037(3) 0.26381(18) 0.7806(2) 0.0433(10) Uani 1 1 d . . . . .
H37 H 0.0313 0.3017 0.7809 0.052 Uiso 1 1 calc R . . . .
C38 C 0.1456(2) 0.23665(15) 0.5513(2) 0.0320(8) Uani 1 1 d . . . . .
H38 H 0.2167 0.2351 0.5691 0.038 Uiso 1 1 calc R . . . .
C39 C 0.1125(2) 0.30031(15) 0.5769(2) 0.0319(8) Uani 1 1 d . . . . .
C40 C 0.1097(3) 0.22315(15) 0.4497(2) 0.0378(9) Uani 1 1 d . . . . .
C41 C 0.1694(3) 0.19723(17) 0.4008(3) 0.0481(10) Uani 1 1 d . . . . .
H41 H 0.2342 0.1903 0.4315 0.058 Uiso 1 1 calc R . . . .
C42 C 0.1397(4) 0.1815(2) 0.3118(3) 0.0681(13) Uani 1 1 d . . . . .
H42 H 0.1824 0.1632 0.2807 0.082 Uiso 1 1 calc R . . . .
C43 C 0.0474(4) 0.19234(19) 0.2675(3) 0.0623(14) Uani 1 1 d . . . . .
C44 C -0.0182(3) 0.21919(18) 0.3108(3) 0.0606(13) Uani 1 1 d . . . . .
H44 H -0.0825 0.2266 0.2787 0.073 Uiso 1 1 calc R . . . .
C45 C 0.0160(3) 0.23471(18) 0.4046(3) 0.0505(11) Uani 1 1 d . . . . .
H45 H -0.0257 0.2532 0.4365 0.061 Uiso 1 1 calc R . . . .
C46 C -0.0680(4) 0.1916(3) 0.1290(4) 0.109(2) Uani 1 1 d . . . . .
H46A H -0.0795 0.1790 0.0647 0.164 Uiso 1 1 calc GR . . . .
H46B H -0.0757 0.2374 0.1326 0.164 Uiso 1 1 calc GR . . . .
H46C H -0.1136 0.1702 0.1567 0.164 Uiso 1 1 calc GR . . . .
C47 C 0.1429(2) 0.36091(16) 0.5476(2) 0.0349(8) Uani 1 1 d . . . . .
C48 C 0.1017(2) 0.41699(16) 0.5674(2) 0.0401(9) Uani 1 1 d . . . . .
H48 H 0.0541 0.4158 0.6003 0.048 Uiso 1 1 calc R . . . .
C49 C 0.1303(3) 0.47461(17) 0.5388(3) 0.0455(10) Uani 1 1 d . . . . .
H49 H 0.1010 0.5126 0.5511 0.055 Uiso 1 1 calc R . . . .
C50 C 0.2008(3) 0.47682(18) 0.4928(3) 0.0489(10) Uani 1 1 d . . . . .
H50 H 0.2209 0.5163 0.4745 0.059 Uiso 1 1 calc R . . . .
C51 C 0.2422(3) 0.42171(18) 0.4732(3) 0.0554(11) Uani 1 1 d . . . . .
H51 H 0.2907 0.4230 0.4413 0.066 Uiso 1 1 calc R . . . .
C52 C 0.2125(3) 0.36444(18) 0.5006(3) 0.0477(10) Uani 1 1 d . . . . .
H52 H 0.2409 0.3266 0.4865 0.057 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
O1 C1 1.208(4) . ?
O2 C22 1.369(4) . ?
O2 C25 1.429(4) . ?
O3 C43 1.401(5) . ?
O3 C46 1.373(6) . ?
N1 N2 1.386(4) . ?
N1 C2 1.464(4) . ?
N1 C11 1.417(4) . ?
N2 C17 1.295(4) . ?
N3 N4 1.390(4) . ?
N3 C10 1.503(4) . ?
N3 C32 1.431(4) . ?
N4 C39 1.287(4) . ?
C1 C2 1.540(4) . ?
C1 C10 1.539(4) . ?
C2 C3 1.533(4) . ?
C2 C18 1.596(5) . ?
C3 C4 1.383(5) . ?
C3 C8 1.391(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.378(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.376(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.393(5) . ?
C8 C9 1.493(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.531(4) . ?
C10 C38 1.578(4) . ?
C11 C12 1.388(4) . ?
C11 C16 1.395(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.388(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.378(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.386(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.380(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.501(4) . ?
C17 C26 1.456(5) . ?
C18 H18 1.0000 . ?
C18 C19 1.510(4) . ?
C19 C20 1.391(4) . ?
C19 C24 1.388(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.373(5) . ?
C21 H21 0.9500 . ?
C21 C22 1.386(5) . ?
C22 C23 1.380(5) . ?
C23 H23 0.9500 . ?
C23 C24 1.390(5) . ?
C24 H24 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C27 1.398(5) . ?
C26 C31 1.389(5) . ?
C27 H27 0.9500 . ?
C27 C28 1.396(5) . ?
C28 H28 0.9500 . ?
C28 C29 1.379(5) . ?
C29 H29 0.9500 . ?
C29 C30 1.389(5) . ?
C30 H30 0.9500 . ?
C30 C31 1.385(5) . ?
C31 H31 0.9500 . ?
C32 C33 1.380(5) . ?
C32 C37 1.390(5) . ?
C33 H33 0.9500 . ?
C33 C34 1.373(5) . ?
C34 H34 0.9500 . ?
C34 C35 1.379(5) . ?
C35 H35 0.9500 . ?
C35 C36 1.375(6) . ?
C36 H36 0.9500 . ?
C36 C37 1.374(5) . ?
C37 H37 0.9500 . ?
C38 H38 1.0000 . ?
C38 C39 1.515(4) . ?
C38 C40 1.518(5) . ?
C39 C47 1.463(5) . ?
C40 C41 1.388(5) . ?
C40 C45 1.381(5) . ?
C41 H41 0.9500 . ?
C41 C42 1.347(5) . ?
C42 H42 0.9500 . ?
C42 C43 1.357(6) . ?
C43 C44 1.407(6) . ?
C44 H44 0.9500 . ?
C44 C45 1.417(5) . ?
C45 H45 0.9500 . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C47 C48 1.397(5) . ?
C47 C52 1.377(5) . ?
C48 H48 0.9500 . ?
C48 C49 1.393(5) . ?
C49 H49 0.9500 . ?
C49 C50 1.376(5) . ?
C50 H50 0.9500 . ?
C50 C51 1.380(5) . ?
C51 H51 0.9500 . ?
C51 C52 1.386(5) . ?
C52 H52 0.9500 . ?

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
C22 O2 C25 116.9(3) . . ?
C46 O3 C43 114.0(4) . . ?
N2 N1 C2 111.2(3) . . ?
N2 N1 C11 115.8(3) . . ?
C11 N1 C2 125.4(3) . . ?
C17 N2 N1 109.7(3) . . ?
N4 N3 C10 110.8(3) . . ?
N4 N3 C32 114.8(3) . . ?
C32 N3 C10 122.1(3) . . ?
C39 N4 N3 109.8(3) . . ?
O1 C1 C2 120.6(3) . . ?
O1 C1 C10 121.2(3) . . ?
C10 C1 C2 117.9(3) . . ?
N1 C2 C1 111.6(3) . . ?
N1 C2 C3 114.7(3) . . ?
N1 C2 C18 101.1(2) . . ?
C1 C2 C18 105.7(2) . . ?
C3 C2 C1 110.6(3) . . ?
C3 C2 C18 112.5(3) . . ?
C4 C3 C2 122.2(3) . . ?
C4 C3 C8 120.4(3) . . ?
C8 C3 C2 117.3(3) . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.1(4) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.7(4) . . ?
C6 C5 H5 120.2 . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.5(4) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 H7 119.7 . . ?
C6 C7 C8 120.6(3) . . ?
C8 C7 H7 119.7 . . ?
C3 C8 C7 118.7(3) . . ?
C3 C8 C9 120.3(3) . . ?
C7 C8 C9 120.9(3) . . ?
C8 C9 H9A 108.2 . . ?
C8 C9 H9B 108.2 . . ?
C8 C9 C10 116.2(3) . . ?
H9A C9 H9B 107.4 . . ?
C10 C9 H9A 108.2 . . ?
C10 C9 H9B 108.2 . . ?
N3 C10 C1 108.8(3) . . ?
N3 C10 C9 114.4(3) . . ?
N3 C10 C38 99.5(2) . . ?
C1 C10 C38 107.3(3) . . ?
C9 C10 C1 112.4(3) . . ?
C9 C10 C38 113.5(3) . . ?
C12 C11 N1 120.1(3) . . ?
C12 C11 C16 118.7(3) . . ?
C16 C11 N1 121.0(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.6(3) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.5(4) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 120.5 . . ?
C13 C14 C15 119.0(4) . . ?
C15 C14 H14 120.5 . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 121.0(4) . . ?
C16 C15 H15 119.5 . . ?
C11 C16 H16 119.9 . . ?
C15 C16 C11 120.2(3) . . ?
C15 C16 H16 119.9 . . ?
N2 C17 C18 113.6(3) . . ?
N2 C17 C26 121.7(3) . . ?
C26 C17 C18 124.7(3) . . ?
C2 C18 H18 109.1 . . ?
C17 C18 C2 100.0(3) . . ?
C17 C18 H18 109.1 . . ?
C17 C18 C19 113.9(3) . . ?
C19 C18 C2 115.0(3) . . ?
C19 C18 H18 109.1 . . ?
C20 C19 C18 121.5(3) . . ?
C24 C19 C18 121.2(3) . . ?
C24 C19 C20 117.3(3) . . ?
C19 C20 H20 119.2 . . ?
C21 C20 C19 121.5(3) . . ?
C21 C20 H20 119.2 . . ?
C20 C21 H21 120.1 . . ?
C20 C21 C22 119.9(3) . . ?
C22 C21 H21 120.1 . . ?
O2 C22 C21 114.8(3) . . ?
O2 C22 C23 125.1(3) . . ?
C23 C22 C21 120.1(3) . . ?
C22 C23 H23 120.6 . . ?
C22 C23 C24 118.8(3) . . ?
C24 C23 H23 120.6 . . ?
C19 C24 C23 122.0(3) . . ?
C19 C24 H24 119.0 . . ?
C23 C24 H24 119.0 . . ?
O2 C25 H25A 109.5 . . ?
O2 C25 H25B 109.5 . . ?
O2 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 C17 120.7(3) . . ?
C31 C26 C17 120.4(3) . . ?
C31 C26 C27 118.8(3) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 C26 120.2(4) . . ?
C28 C27 H27 119.9 . . ?
C27 C28 H28 119.7 . . ?
C29 C28 C27 120.6(4) . . ?
C29 C28 H28 119.7 . . ?
C28 C29 H29 120.5 . . ?
C28 C29 C30 119.0(4) . . ?
C30 C29 H29 120.5 . . ?
C29 C30 H30 119.5 . . ?
C31 C30 C29 120.9(4) . . ?
C31 C30 H30 119.5 . . ?
C26 C31 H31 119.8 . . ?
C30 C31 C26 120.4(4) . . ?
C30 C31 H31 119.8 . . ?
C33 C32 N3 119.6(3) . . ?
C33 C32 C37 119.3(3) . . ?
C37 C32 N3 121.1(3) . . ?
C32 C33 H33 119.8 . . ?
C34 C33 C32 120.4(4) . . ?
C34 C33 H33 119.8 . . ?
C33 C34 H34 120.0 . . ?
C33 C34 C35 120.1(4) . . ?
C35 C34 H34 120.0 . . ?
C34 C35 H35 120.2 . . ?
C36 C35 C34 119.7(4) . . ?
C36 C35 H35 120.2 . . ?
C35 C36 H36 119.7 . . ?
C37 C36 C35 120.6(4) . . ?
C37 C36 H36 119.7 . . ?
C32 C37 H37 120.1 . . ?
C36 C37 C32 119.8(4) . . ?
C36 C37 H37 120.1 . . ?
C10 C38 H38 109.4 . . ?
C39 C38 C10 101.5(3) . . ?
C39 C38 H38 109.4 . . ?
C39 C38 C40 112.1(3) . . ?
C40 C38 C10 114.6(3) . . ?
C40 C38 H38 109.4 . . ?
N4 C39 C38 113.0(3) . . ?
N4 C39 C47 122.5(3) . . ?
C47 C39 C38 124.4(3) . . ?
C41 C40 C38 120.9(3) . . ?
C45 C40 C38 120.6(3) . . ?
C45 C40 C41 118.5(3) . . ?
C40 C41 H41 118.4 . . ?
C42 C41 C40 123.1(4) . . ?
C42 C41 H41 118.4 . . ?
C41 C42 H42 120.8 . . ?
C41 C42 C43 118.5(4) . . ?
C43 C42 H42 120.8 . . ?
O3 C43 C44 122.7(5) . . ?
C42 C43 O3 114.6(5) . . ?
C42 C43 C44 122.7(4) . . ?
C43 C44 H44 121.6 . . ?
C43 C44 C45 116.9(4) . . ?
C45 C44 H44 121.6 . . ?
C40 C45 C44 120.4(4) . . ?
C40 C45 H45 119.8 . . ?
C44 C45 H45 119.8 . . ?
O3 C46 H46A 109.5 . . ?
O3 C46 H46B 109.5 . . ?
O3 C46 H46C 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C48 C47 C39 120.2(3) . . ?
C52 C47 C39 121.4(3) . . ?
C52 C47 C48 118.3(3) . . ?
C47 C48 H48 119.9 . . ?
C49 C48 C47 120.1(4) . . ?
C49 C48 H48 119.9 . . ?
C48 C49 H49 119.8 . . ?
C50 C49 C48 120.3(4) . . ?
C50 C49 H49 119.8 . . ?
C49 C50 H50 120.0 . . ?
C49 C50 C51 120.0(4) . . ?
C51 C50 H50 120.0 . . ?
C50 C51 H51 120.3 . . ?
C50 C51 C52 119.5(4) . . ?
C52 C51 H51 120.3 . . ?
C47 C52 C51 121.7(4) . . ?
C47 C52 H52 119.1 . . ?
C51 C52 H52 119.1 . . ?

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 C2 N1 13.0(4) . . . . ?
O1 C1 C2 C3 141.9(3) . . . . ?
O1 C1 C2 C18 -96.0(3) . . . . ?
O1 C1 C10 N3 -50.9(4) . . . . ?
O1 C1 C10 C9 -178.7(3) . . . . ?
O1 C1 C10 C38 55.8(4) . . . . ?
O2 C22 C23 C24 -175.7(3) . . . . ?
O3 C43 C44 C45 -179.7(3) . . . . ?
N1 N2 C17 C18 -1.5(4) . . . . ?
N1 N2 C17 C26 178.0(3) . . . . ?
N1 C2 C3 C4 -14.3(5) . . . . ?
N1 C2 C3 C8 169.6(3) . . . . ?
N1 C2 C18 C17 -18.8(3) . . . . ?
N1 C2 C18 C19 103.7(3) . . . . ?
N1 C11 C12 C13 -175.3(3) . . . . ?
N1 C11 C16 C15 175.3(3) . . . . ?
N2 N1 C2 C1 -91.9(3) . . . . ?
N2 N1 C2 C3 141.4(3) . . . . ?
N2 N1 C2 C18 20.1(3) . . . . ?
N2 N1 C11 C12 -19.0(4) . . . . ?
N2 N1 C11 C16 165.8(3) . . . . ?
N2 C17 C18 C2 13.4(3) . . . . ?
N2 C17 C18 C19 -109.8(3) . . . . ?
N2 C17 C26 C27 -175.2(3) . . . . ?
N2 C17 C26 C31 0.8(5) . . . . ?
N3 N4 C39 C38 -1.1(4) . . . . ?
N3 N4 C39 C47 175.4(3) . . . . ?
N3 C10 C38 C39 20.2(3) . . . . ?
N3 C10 C38 C40 -100.9(3) . . . . ?
N3 C32 C33 C34 178.9(3) . . . . ?
N3 C32 C37 C36 178.8(3) . . . . ?
N4 N3 C10 C1 89.0(3) . . . . ?
N4 N3 C10 C9 -144.3(3) . . . . ?
N4 N3 C10 C38 -23.0(3) . . . . ?
N4 N3 C32 C33 156.9(3) . . . . ?
N4 N3 C32 C37 -20.3(4) . . . . ?
N4 C39 C47 C48 -2.2(5) . . . . ?
N4 C39 C47 C52 177.5(3) . . . . ?
C1 C2 C3 C4 -141.5(3) . . . . ?
C1 C2 C3 C8 42.4(4) . . . . ?
C1 C2 C18 C17 97.6(3) . . . . ?
C1 C2 C18 C19 -139.9(3) . . . . ?
C1 C10 C38 C39 -93.1(3) . . . . ?
C1 C10 C38 C40 145.9(3) . . . . ?
C2 N1 N2 C17 -12.9(3) . . . . ?
C2 N1 C11 C12 -165.8(3) . . . . ?
C2 N1 C11 C16 19.0(5) . . . . ?
C2 C1 C10 N3 134.7(3) . . . . ?
C2 C1 C10 C9 7.0(4) . . . . ?
C2 C1 C10 C38 -118.5(3) . . . . ?
C2 C3 C4 C5 -174.1(4) . . . . ?
C2 C3 C8 C7 173.6(3) . . . . ?
C2 C3 C8 C9 -3.5(5) . . . . ?
C2 C18 C19 C20 116.1(3) . . . . ?
C2 C18 C19 C24 -61.9(4) . . . . ?
C3 C2 C18 C17 -141.6(3) . . . . ?
C3 C2 C18 C19 -19.1(4) . . . . ?
C3 C4 C5 C6 0.1(7) . . . . ?
C3 C8 C9 C10 -36.7(5) . . . . ?
C4 C3 C8 C7 -2.5(5) . . . . ?
C4 C3 C8 C9 -179.6(3) . . . . ?
C4 C5 C6 C7 -1.3(7) . . . . ?
C5 C6 C7 C8 0.6(6) . . . . ?
C6 C7 C8 C3 1.3(5) . . . . ?
C6 C7 C8 C9 178.4(3) . . . . ?
C7 C8 C9 C10 146.2(3) . . . . ?
C8 C3 C4 C5 1.8(6) . . . . ?
C8 C9 C10 N3 -91.8(4) . . . . ?
C8 C9 C10 C1 33.0(4) . . . . ?
C8 C9 C10 C38 155.0(3) . . . . ?
C9 C10 C38 C39 142.1(3) . . . . ?
C9 C10 C38 C40 21.1(4) . . . . ?
C10 N3 N4 C39 16.4(4) . . . . ?
C10 N3 C32 C33 -64.3(4) . . . . ?
C10 N3 C32 C37 118.5(4) . . . . ?
C10 C1 C2 N1 -172.6(3) . . . . ?
C10 C1 C2 C3 -43.7(4) . . . . ?
C10 C1 C2 C18 78.3(3) . . . . ?
C10 C38 C39 N4 -13.2(3) . . . . ?
C10 C38 C39 C47 170.3(3) . . . . ?
C10 C38 C40 C41 -108.5(4) . . . . ?
C10 C38 C40 C45 69.6(4) . . . . ?
C11 N1 N2 C17 -164.4(3) . . . . ?
C11 N1 C2 C1 56.2(4) . . . . ?
C11 N1 C2 C3 -70.5(4) . . . . ?
C11 N1 C2 C18 168.2(3) . . . . ?
C11 C12 C13 C14 0.3(5) . . . . ?
C12 C11 C16 C15 0.0(5) . . . . ?
C12 C13 C14 C15 -0.5(5) . . . . ?
C13 C14 C15 C16 0.5(6) . . . . ?
C14 C15 C16 C11 -0.2(6) . . . . ?
C16 C11 C12 C13 -0.1(5) . . . . ?
C17 C18 C19 C20 -129.2(3) . . . . ?
C17 C18 C19 C24 52.8(4) . . . . ?
C17 C26 C27 C28 175.6(3) . . . . ?
C17 C26 C31 C30 -175.1(3) . . . . ?
C18 C2 C3 C4 100.5(4) . . . . ?
C18 C2 C3 C8 -75.5(4) . . . . ?
C18 C17 C26 C27 4.3(5) . . . . ?
C18 C17 C26 C31 -179.7(3) . . . . ?
C18 C19 C20 C21 -175.9(3) . . . . ?
C18 C19 C24 C23 174.2(3) . . . . ?
C19 C20 C21 C22 2.2(5) . . . . ?
C20 C19 C24 C23 -3.9(5) . . . . ?
C20 C21 C22 O2 174.2(3) . . . . ?
C20 C21 C22 C23 -5.2(5) . . . . ?
C21 C22 C23 C24 3.6(5) . . . . ?
C22 C23 C24 C19 1.1(6) . . . . ?
C24 C19 C20 C21 2.2(5) . . . . ?
C25 O2 C22 C21 -171.3(3) . . . . ?
C25 O2 C22 C23 8.0(5) . . . . ?
C26 C17 C18 C2 -166.1(3) . . . . ?
C26 C17 C18 C19 70.6(4) . . . . ?
C26 C27 C28 C29 -0.8(6) . . . . ?
C27 C26 C31 C30 1.0(5) . . . . ?
C27 C28 C29 C30 1.6(6) . . . . ?
C28 C29 C30 C31 -1.1(6) . . . . ?
C29 C30 C31 C26 -0.2(6) . . . . ?
C31 C26 C27 C28 -0.5(5) . . . . ?
C32 N3 N4 C39 159.8(3) . . . . ?
C32 N3 C10 C1 -51.2(4) . . . . ?
C32 N3 C10 C9 75.4(4) . . . . ?
C32 N3 C10 C38 -163.3(3) . . . . ?
C32 C33 C34 C35 3.8(6) . . . . ?
C33 C32 C37 C36 1.6(6) . . . . ?
C33 C34 C35 C36 -1.5(6) . . . . ?
C34 C35 C36 C37 -0.7(7) . . . . ?
C35 C36 C37 C32 0.6(6) . . . . ?
C37 C32 C33 C34 -3.8(5) . . . . ?
C38 C39 C47 C48 173.9(3) . . . . ?
C38 C39 C47 C52 -6.3(5) . . . . ?
C38 C40 C41 C42 176.6(3) . . . . ?
C38 C40 C45 C44 -177.0(3) . . . . ?
C39 C38 C40 C41 136.5(3) . . . . ?
C39 C38 C40 C45 -45.4(4) . . . . ?
C39 C47 C48 C49 -179.5(3) . . . . ?
C39 C47 C52 C51 -179.5(3) . . . . ?
C40 C38 C39 N4 109.6(3) . . . . ?
C40 C38 C39 C47 -66.9(4) . . . . ?
C40 C41 C42 C43 1.0(6) . . . . ?
C41 C40 C45 C44 1.2(5) . . . . ?
C41 C42 C43 O3 179.4(4) . . . . ?
C41 C42 C43 C44 -0.1(6) . . . . ?
C42 C43 C44 C45 -0.2(6) . . . . ?
C43 C44 C45 C40 -0.4(5) . . . . ?
C45 C40 C41 C42 -1.5(6) . . . . ?
C46 O3 C43 C42 -174.3(4) . . . . ?
C46 O3 C43 C44 5.2(6) . . . . ?
C47 C48 C49 C50 -1.5(5) . . . . ?
C48 C47 C52 C51 0.3(6) . . . . ?
C48 C49 C50 C51 1.2(6) . . . . ?
C49 C50 C51 C52 -0.2(6) . . . . ?
C50 C51 C52 C47 -0.5(6) . . . . ?
C52 C47 C48 C49 0.7(5) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method Chloroform/Ethanol
