# 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 2017

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

data_5k
_database_code_depnum_ccdc_archive 'CCDC 1498655'
_audit_update_record             
;
2016-08-10 deposited with the CCDC.
2017-06-28 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT930_5k                  
;
PROBLEM: Check Twin Law ( 0 0  1)[ 1 0  2] Estimated BASF       0.09
RESPONSE: This was checked and found not to be significant.
;
# Added during the CSD deposition process: Wednesday 10 August 2016 03:58 PM
# end Validation Reply Form

_audit_creation_date             2015-11-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C24 H19 N3 O'
_chemical_formula_sum            'C24 H19 N3 O'
_chemical_formula_weight         365.42
_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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.1159(6)
_cell_length_b                   15.3254(7)
_cell_length_c                   18.2305(9)
_cell_angle_alpha                90
_cell_angle_beta                 112.383(3)
_cell_angle_gamma                90
_cell_volume                     3646.7(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3350
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.82
_cell_measurement_theta_min      2.32
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6629
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0676 before and 0.0593 after correction.
The Ratio of minimum to maximum transmission is 0.8891.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.13
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0808
_diffrn_reflns_av_unetI/netI     0.0776
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            32948
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.971
_diffrn_reflns_theta_min         1.560
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5743
_reflns_number_total             8712
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     509
_refine_ls_number_reflns         8712
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1235
_refine_ls_R_factor_gt           0.0801
_refine_ls_restrained_S_all      1.083
_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)+(0.0416P)²+12.5316P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1874
_refine_ls_wR_factor_ref         0.2063
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C35(H35A,H35B), C36(H36A,H36B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C17(H17), C18(H18), C20(H20),
 C21(H21), N4(H4A), C26(H26), C27(H27), C28(H28), C29(H29), C41(H41), C42(H42),
 C44(H44), C45(H45)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C24(H24A,H24B,H24C), C46(H46A,H46B,H46C), C48(H48A,H48B,
 H48C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.21181(18) 0.05328(16) 0.49247(15) 0.0195(5) Uani 1 1 d . . . . .
N1 N 0.5378(2) -0.11540(18) 0.58624(17) 0.0164(6) Uani 1 1 d . . . . .
H1 H 0.4790 -0.1371 0.5539 0.020 Uiso 1 1 calc R . . . .
N2 N 0.3808(2) 0.01236(18) 0.55066(16) 0.0141(6) Uani 1 1 d . . . . .
N3 N 0.1788(2) 0.2658(2) 0.53448(19) 0.0219(7) Uani 1 1 d . . . . .
C1 C 0.6271(3) -0.1609(2) 0.6207(2) 0.0154(7) Uani 1 1 d . . . . .
C2 C 0.6472(3) -0.2495(2) 0.6156(2) 0.0219(8) Uani 1 1 d . . . . .
H2 H 0.5952 -0.2883 0.5840 0.026 Uiso 1 1 calc R . . . .
C3 C 0.7457(3) -0.2784(3) 0.6581(2) 0.0290(9) Uani 1 1 d . . . . .
H3 H 0.7612 -0.3384 0.6559 0.035 Uiso 1 1 calc R . . . .
C4 C 0.8234(3) -0.2218(3) 0.7044(3) 0.0300(9) Uani 1 1 d . . . . .
H4 H 0.8904 -0.2437 0.7325 0.036 Uiso 1 1 calc R . . . .
C5 C 0.8030(3) -0.1339(3) 0.7094(2) 0.0252(8) Uani 1 1 d . . . . .
H5 H 0.8560 -0.0956 0.7404 0.030 Uiso 1 1 calc R . . . .
C6 C 0.7043(3) -0.1023(2) 0.6685(2) 0.0174(7) Uani 1 1 d . . . . .
C7 C 0.6561(3) -0.0192(2) 0.6608(2) 0.0159(7) Uani 1 1 d . . . . .
C8 C 0.5555(3) -0.0299(2) 0.6107(2) 0.0148(7) Uani 1 1 d . . . . .
C9 C 0.4787(2) 0.0363(2) 0.59186(19) 0.0138(7) Uani 1 1 d . . . . .
C10 C 0.5109(3) 0.1217(2) 0.6187(2) 0.0156(7) Uani 1 1 d . . . . .
C11 C 0.6245(3) 0.1412(2) 0.6568(2) 0.0207(8) Uani 1 1 d . . . . .
H11A H 0.6346 0.1912 0.6935 0.025 Uiso 1 1 calc R . . . .
H11B H 0.6487 0.1594 0.6148 0.025 Uiso 1 1 calc R . . . .
C12 C 0.6906(3) 0.0653(2) 0.7027(2) 0.0189(7) Uani 1 1 d . . . . .
H12A H 0.7628 0.0760 0.7098 0.023 Uiso 1 1 calc R . . . .
H12B H 0.6875 0.0620 0.7560 0.023 Uiso 1 1 calc R . . . .
C13 C 0.4342(3) 0.1853(2) 0.60395(19) 0.0146(7) Uani 1 1 d . . . . .
C14 C 0.3314(3) 0.1594(2) 0.5637(2) 0.0157(7) Uani 1 1 d . . . . .
C15 C 0.3103(3) 0.0731(2) 0.5362(2) 0.0151(7) Uani 1 1 d . . . . .
C16 C 0.4597(3) 0.2774(2) 0.6283(2) 0.0156(7) Uani 1 1 d . . . . .
C17 C 0.5242(3) 0.3240(2) 0.6006(2) 0.0192(7) Uani 1 1 d . . . . .
H17 H 0.5536 0.2957 0.5679 0.023 Uiso 1 1 calc R . . . .
C18 C 0.5461(3) 0.4110(2) 0.6201(2) 0.0221(8) Uani 1 1 d . . . . .
H18 H 0.5897 0.4416 0.6002 0.027 Uiso 1 1 calc R . . . .
C19 C 0.5051(3) 0.4547(2) 0.6685(2) 0.0214(8) Uani 1 1 d . . . . .
C20 C 0.4430(3) 0.4075(2) 0.6976(2) 0.0215(8) Uani 1 1 d . . . . .
H20 H 0.4158 0.4354 0.7319 0.026 Uiso 1 1 calc R . . . .
C21 C 0.4197(3) 0.3202(2) 0.6778(2) 0.0190(7) Uani 1 1 d . . . . .
H21 H 0.3764 0.2895 0.6981 0.023 Uiso 1 1 calc R . . . .
C22 C 0.5269(3) 0.5502(2) 0.6882(3) 0.0303(9) Uani 1 1 d . . . . .
H22A H 0.5956 0.5644 0.6902 0.045 Uiso 1 1 calc GR . . . .
H22B H 0.5234 0.5624 0.7398 0.045 Uiso 1 1 calc GR . . . .
H22C H 0.4760 0.5857 0.6473 0.045 Uiso 1 1 calc GR . . . .
C23 C 0.2476(3) 0.2202(2) 0.5466(2) 0.0161(7) Uani 1 1 d . . . . .
C24 C 0.1946(3) -0.0332(2) 0.4575(2) 0.0200(7) Uani 1 1 d . . . . .
H24A H 0.1229 -0.0388 0.4212 0.030 Uiso 1 1 calc GR . . . .
H24B H 0.2101 -0.0772 0.4995 0.030 Uiso 1 1 calc GR . . . .
H24C H 0.2393 -0.0422 0.4281 0.030 Uiso 1 1 calc GR . . . .
O2 O 0.30773(18) 0.54486(16) 0.51203(15) 0.0187(5) Uani 1 1 d . . . . .
N4 N 0.0455(2) 0.39169(18) 0.58714(17) 0.0159(6) Uani 1 1 d . . . . .
H4A H 0.0785 0.3662 0.5607 0.019 Uiso 1 1 calc R . . . .
N5 N 0.1834(2) 0.51239(18) 0.56032(17) 0.0150(6) Uani 1 1 d . . . . .
N6 N 0.3620(2) 0.7624(2) 0.52674(18) 0.0204(7) Uani 1 1 d . . . . .
C25 C -0.0224(2) 0.3515(2) 0.6145(2) 0.0162(7) Uani 1 1 d . . . . .
C26 C -0.0543(3) 0.2662(2) 0.6090(2) 0.0179(7) Uani 1 1 d . . . . .
H26 H -0.0287 0.2234 0.5836 0.022 Uiso 1 1 calc R . . . .
C27 C -0.1248(3) 0.2446(2) 0.6416(2) 0.0205(8) Uani 1 1 d . . . . .
H27 H -0.1476 0.1859 0.6386 0.025 Uiso 1 1 calc R . . . .
C28 C -0.1638(3) 0.3072(3) 0.6791(2) 0.0233(8) Uani 1 1 d . . . . .
H28 H -0.2129 0.2904 0.7004 0.028 Uiso 1 1 calc R . . . .
C29 C -0.1314(3) 0.3926(2) 0.6852(2) 0.0210(8) Uani 1 1 d . . . . .
H29 H -0.1575 0.4348 0.7107 0.025 Uiso 1 1 calc R . . . .
C30 C -0.0593(2) 0.4162(2) 0.6532(2) 0.0154(7) Uani 1 1 d . . . . .
C31 C -0.0095(3) 0.4964(2) 0.6492(2) 0.0166(7) Uani 1 1 d . . . . .
C32 C 0.0528(2) 0.4785(2) 0.6083(2) 0.0151(7) Uani 1 1 d . . . . .
C33 C 0.1177(2) 0.5419(2) 0.5926(2) 0.0145(7) Uani 1 1 d . . . . .
C34 C 0.1075(2) 0.6302(2) 0.61146(19) 0.0145(7) Uani 1 1 d . . . . .
C35 C 0.0243(3) 0.6544(2) 0.6407(2) 0.0195(7) Uani 1 1 d . . . . .
H35A H 0.0474 0.7058 0.6759 0.023 Uiso 1 1 calc R . . . .
H35B H -0.0373 0.6720 0.5945 0.023 Uiso 1 1 calc R . . . .
C36 C -0.0063(3) 0.5839(2) 0.6851(2) 0.0188(7) Uani 1 1 d . . . . .
H36A H 0.0431 0.5829 0.7408 0.023 Uiso 1 1 calc R . . . .
H36B H -0.0747 0.5977 0.6853 0.023 Uiso 1 1 calc R . . . .
C37 C 0.1730(2) 0.6905(2) 0.59712(19) 0.0141(7) Uani 1 1 d . . . . .
C38 C 0.2432(2) 0.6600(2) 0.5654(2) 0.0154(7) Uani 1 1 d . . . . .
C39 C 0.2432(3) 0.5702(2) 0.5465(2) 0.0155(7) Uani 1 1 d . . . . .
C40 C 0.1672(3) 0.7854(2) 0.6116(2) 0.0153(7) Uani 1 1 d . . . . .
C41 C 0.0732(3) 0.8296(2) 0.5787(2) 0.0184(7) Uani 1 1 d . . . . .
H41 H 0.0133 0.7983 0.5476 0.022 Uiso 1 1 calc R . . . .
C42 C 0.0668(3) 0.9182(2) 0.5910(2) 0.0202(8) Uani 1 1 d . . . . .
H42 H 0.0022 0.9465 0.5688 0.024 Uiso 1 1 calc R . . . .
C43 C 0.1530(3) 0.9665(2) 0.6350(2) 0.0196(7) Uani 1 1 d . . . . .
C44 C 0.2462(3) 0.9230(2) 0.6670(2) 0.0198(7) Uani 1 1 d . . . . .
H44 H 0.3062 0.9549 0.6972 0.024 Uiso 1 1 calc R . . . .
C45 C 0.2538(3) 0.8338(2) 0.6557(2) 0.0185(7) Uani 1 1 d . . . . .
H45 H 0.3185 0.8058 0.6783 0.022 Uiso 1 1 calc R . . . .
C46 C 0.1444(3) 1.0632(2) 0.6484(3) 0.0286(9) Uani 1 1 d . . . . .
H46A H 0.0996 1.0722 0.6776 0.043 Uiso 1 1 calc GR . . . .
H46B H 0.1155 1.0931 0.5971 0.043 Uiso 1 1 calc GR . . . .
H46C H 0.2126 1.0869 0.6791 0.043 Uiso 1 1 calc GR . . . .
C47 C 0.3087(3) 0.7173(2) 0.5440(2) 0.0159(7) Uani 1 1 d . . . . .
C48 C 0.2967(3) 0.4550(2) 0.4853(2) 0.0206(8) Uani 1 1 d . . . . .
H48A H 0.2274 0.4458 0.4458 0.031 Uiso 1 1 calc GR . . . .
H48B H 0.3085 0.4161 0.5306 0.031 Uiso 1 1 calc GR . . . .
H48C H 0.3469 0.4424 0.4615 0.031 Uiso 1 1 calc GR . . . .


_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 C15 1.347(4) . ?
O1 C24 1.451(4) . ?
N1 H1 0.8800 . ?
N1 C1 1.366(4) . ?
N1 C8 1.375(4) . ?
N2 C9 1.349(4) . ?
N2 C15 1.314(4) . ?
N3 C23 1.148(4) . ?
C1 C2 1.397(5) . ?
C1 C6 1.426(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.401(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.388(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.394(5) . ?
C6 C7 1.425(5) . ?
C7 C8 1.375(5) . ?
C7 C12 1.488(5) . ?
C8 C9 1.428(5) . ?
C9 C10 1.411(5) . ?
C10 C11 1.515(5) . ?
C10 C13 1.405(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.526(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.410(5) . ?
C13 C16 1.482(5) . ?
C14 C15 1.407(5) . ?
C14 C23 1.444(5) . ?
C16 C17 1.395(5) . ?
C16 C21 1.396(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.383(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.396(5) . ?
C19 C20 1.389(5) . ?
C19 C22 1.511(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.393(5) . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
O2 C39 1.346(4) . ?
O2 C48 1.449(4) . ?
N4 H4A 0.8800 . ?
N4 C25 1.382(4) . ?
N4 C32 1.379(4) . ?
N5 C33 1.351(4) . ?
N5 C39 1.313(4) . ?
N6 C47 1.151(4) . ?
C25 C26 1.375(5) . ?
C25 C30 1.426(5) . ?
C26 H26 0.9500 . ?
C26 C27 1.378(5) . ?
C27 H27 0.9500 . ?
C27 C28 1.406(5) . ?
C28 H28 0.9500 . ?
C28 C29 1.377(5) . ?
C29 H29 0.9500 . ?
C29 C30 1.399(5) . ?
C30 C31 1.432(5) . ?
C31 C32 1.379(5) . ?
C31 C36 1.485(5) . ?
C32 C33 1.436(5) . ?
C33 C34 1.418(5) . ?
C34 C35 1.510(5) . ?
C34 C37 1.400(5) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C35 C36 1.506(5) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 C38 1.404(5) . ?
C37 C40 1.487(5) . ?
C38 C39 1.419(5) . ?
C38 C47 1.432(5) . ?
C40 C41 1.405(5) . ?
C40 C45 1.393(5) . ?
C41 H41 0.9500 . ?
C41 C42 1.385(5) . ?
C42 H42 0.9500 . ?
C42 C43 1.389(5) . ?
C43 C44 1.390(5) . ?
C43 C46 1.514(5) . ?
C44 H44 0.9500 . ?
C44 C45 1.392(5) . ?
C45 H45 0.9500 . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 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
C15 O1 C24 115.3(3) . . ?
C1 N1 H1 125.8 . . ?
C1 N1 C8 108.4(3) . . ?
C8 N1 H1 125.8 . . ?
C15 N2 C9 117.2(3) . . ?
N1 C1 C2 129.9(3) . . ?
N1 C1 C6 108.4(3) . . ?
C2 C1 C6 121.7(3) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 C1 117.4(3) . . ?
C3 C2 H2 121.3 . . ?
C2 C3 H3 119.0 . . ?
C2 C3 C4 121.9(4) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.4(4) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.3 . . ?
C4 C5 C6 119.5(4) . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C1 118.9(3) . . ?
C5 C6 C7 134.9(3) . . ?
C7 C6 C1 106.2(3) . . ?
C6 C7 C12 132.6(3) . . ?
C8 C7 C6 106.9(3) . . ?
C8 C7 C12 119.9(3) . . ?
N1 C8 C9 124.8(3) . . ?
C7 C8 N1 110.1(3) . . ?
C7 C8 C9 124.9(3) . . ?
N2 C9 C8 117.7(3) . . ?
N2 C9 C10 124.8(3) . . ?
C10 C9 C8 117.5(3) . . ?
C9 C10 C11 119.1(3) . . ?
C13 C10 C9 117.1(3) . . ?
C13 C10 C11 123.7(3) . . ?
C10 C11 H11A 108.5 . . ?
C10 C11 H11B 108.5 . . ?
C10 C11 C12 114.9(3) . . ?
H11A C11 H11B 107.5 . . ?
C12 C11 H11A 108.5 . . ?
C12 C11 H11B 108.5 . . ?
C7 C12 C11 111.7(3) . . ?
C7 C12 H12A 109.3 . . ?
C7 C12 H12B 109.3 . . ?
C11 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
C10 C13 C14 118.0(3) . . ?
C10 C13 C16 121.5(3) . . ?
C14 C13 C16 120.5(3) . . ?
C13 C14 C23 121.8(3) . . ?
C15 C14 C13 119.1(3) . . ?
C15 C14 C23 119.0(3) . . ?
O1 C15 C14 117.0(3) . . ?
N2 C15 O1 119.4(3) . . ?
N2 C15 C14 123.6(3) . . ?
C17 C16 C13 119.8(3) . . ?
C17 C16 C21 118.3(3) . . ?
C21 C16 C13 121.9(3) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.8(3) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 119.4 . . ?
C17 C18 C19 121.3(3) . . ?
C19 C18 H18 119.4 . . ?
C18 C19 C22 121.2(4) . . ?
C20 C19 C18 117.8(3) . . ?
C20 C19 C22 121.0(3) . . ?
C19 C20 H20 119.3 . . ?
C19 C20 C21 121.5(3) . . ?
C21 C20 H20 119.3 . . ?
C16 C21 H21 119.8 . . ?
C20 C21 C16 120.4(3) . . ?
C20 C21 H21 119.8 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N3 C23 C14 176.8(4) . . ?
O1 C24 H24A 109.5 . . ?
O1 C24 H24B 109.5 . . ?
O1 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C39 O2 C48 115.2(3) . . ?
C25 N4 H4A 125.7 . . ?
C32 N4 H4A 125.7 . . ?
C32 N4 C25 108.5(3) . . ?
C39 N5 C33 117.1(3) . . ?
N4 C25 C30 107.6(3) . . ?
C26 C25 N4 130.6(3) . . ?
C26 C25 C30 121.7(3) . . ?
C25 C26 H26 121.1 . . ?
C25 C26 C27 117.9(3) . . ?
C27 C26 H26 121.1 . . ?
C26 C27 H27 119.1 . . ?
C26 C27 C28 121.8(3) . . ?
C28 C27 H27 119.1 . . ?
C27 C28 H28 119.8 . . ?
C29 C28 C27 120.5(3) . . ?
C29 C28 H28 119.8 . . ?
C28 C29 H29 120.5 . . ?
C28 C29 C30 119.0(3) . . ?
C30 C29 H29 120.5 . . ?
C25 C30 C31 107.0(3) . . ?
C29 C30 C25 119.2(3) . . ?
C29 C30 C31 133.8(3) . . ?
C30 C31 C36 133.3(3) . . ?
C32 C31 C30 106.5(3) . . ?
C32 C31 C36 119.9(3) . . ?
N4 C32 C31 110.4(3) . . ?
N4 C32 C33 125.6(3) . . ?
C31 C32 C33 124.0(3) . . ?
N5 C33 C32 117.2(3) . . ?
N5 C33 C34 125.1(3) . . ?
C34 C33 C32 117.8(3) . . ?
C33 C34 C35 118.9(3) . . ?
C37 C34 C33 116.7(3) . . ?
C37 C34 C35 124.2(3) . . ?
C34 C35 H35A 108.3 . . ?
C34 C35 H35B 108.3 . . ?
H35A C35 H35B 107.4 . . ?
C36 C35 C34 115.8(3) . . ?
C36 C35 H35A 108.3 . . ?
C36 C35 H35B 108.3 . . ?
C31 C36 C35 112.2(3) . . ?
C31 C36 H36A 109.2 . . ?
C31 C36 H36B 109.2 . . ?
C35 C36 H36A 109.2 . . ?
C35 C36 H36B 109.2 . . ?
H36A C36 H36B 107.9 . . ?
C34 C37 C38 118.5(3) . . ?
C34 C37 C40 121.9(3) . . ?
C38 C37 C40 119.6(3) . . ?
C37 C38 C39 119.2(3) . . ?
C37 C38 C47 122.6(3) . . ?
C39 C38 C47 118.0(3) . . ?
O2 C39 C38 117.1(3) . . ?
N5 C39 O2 119.6(3) . . ?
N5 C39 C38 123.3(3) . . ?
C41 C40 C37 120.1(3) . . ?
C45 C40 C37 121.9(3) . . ?
C45 C40 C41 117.9(3) . . ?
C40 C41 H41 119.6 . . ?
C42 C41 C40 120.9(3) . . ?
C42 C41 H41 119.6 . . ?
C41 C42 H42 119.3 . . ?
C41 C42 C43 121.3(3) . . ?
C43 C42 H42 119.3 . . ?
C42 C43 C44 117.9(3) . . ?
C42 C43 C46 120.6(3) . . ?
C44 C43 C46 121.5(3) . . ?
C43 C44 H44 119.2 . . ?
C43 C44 C45 121.5(3) . . ?
C45 C44 H44 119.2 . . ?
C40 C45 H45 119.7 . . ?
C44 C45 C40 120.5(3) . . ?
C44 C45 H45 119.7 . . ?
C43 C46 H46A 109.5 . . ?
C43 C46 H46B 109.5 . . ?
C43 C46 H46C 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
N6 C47 C38 179.1(4) . . ?
O2 C48 H48A 109.5 . . ?
O2 C48 H48B 109.5 . . ?
O2 C48 H48C 109.5 . . ?
H48A C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?

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
N1 C1 C2 C3 -179.2(4) . . . . ?
N1 C1 C6 C5 -179.4(3) . . . . ?
N1 C1 C6 C7 0.1(4) . . . . ?
N1 C8 C9 N2 3.7(5) . . . . ?
N1 C8 C9 C10 -177.1(3) . . . . ?
N2 C9 C10 C11 -173.7(3) . . . . ?
N2 C9 C10 C13 2.7(5) . . . . ?
C1 N1 C8 C7 0.2(4) . . . . ?
C1 N1 C8 C9 -175.1(3) . . . . ?
C1 C2 C3 C4 -0.5(6) . . . . ?
C1 C6 C7 C8 0.0(4) . . . . ?
C1 C6 C7 C12 171.2(4) . . . . ?
C2 C1 C6 C5 1.8(5) . . . . ?
C2 C1 C6 C7 -178.7(3) . . . . ?
C2 C3 C4 C5 0.5(7) . . . . ?
C3 C4 C5 C6 0.6(7) . . . . ?
C4 C5 C6 C1 -1.7(6) . . . . ?
C4 C5 C6 C7 179.0(4) . . . . ?
C5 C6 C7 C8 179.4(4) . . . . ?
C5 C6 C7 C12 -9.4(7) . . . . ?
C6 C1 C2 C3 -0.7(5) . . . . ?
C6 C7 C8 N1 -0.1(4) . . . . ?
C6 C7 C8 C9 175.1(3) . . . . ?
C6 C7 C12 C11 163.0(4) . . . . ?
C7 C8 C9 N2 -170.9(3) . . . . ?
C7 C8 C9 C10 8.3(5) . . . . ?
C8 N1 C1 C2 178.5(4) . . . . ?
C8 N1 C1 C6 -0.2(4) . . . . ?
C8 C7 C12 C11 -26.8(5) . . . . ?
C8 C9 C10 C11 7.2(5) . . . . ?
C8 C9 C10 C13 -176.4(3) . . . . ?
C9 N2 C15 O1 177.3(3) . . . . ?
C9 N2 C15 C14 -2.5(5) . . . . ?
C9 C10 C11 C12 -31.8(5) . . . . ?
C9 C10 C13 C14 0.0(5) . . . . ?
C9 C10 C13 C16 -178.9(3) . . . . ?
C10 C11 C12 C7 40.0(4) . . . . ?
C10 C13 C14 C15 -3.6(5) . . . . ?
C10 C13 C14 C23 179.5(3) . . . . ?
C10 C13 C16 C17 57.6(5) . . . . ?
C10 C13 C16 C21 -123.3(4) . . . . ?
C11 C10 C13 C14 176.2(3) . . . . ?
C11 C10 C13 C16 -2.7(5) . . . . ?
C12 C7 C8 N1 -172.6(3) . . . . ?
C12 C7 C8 C9 2.6(5) . . . . ?
C13 C10 C11 C12 152.0(3) . . . . ?
C13 C14 C15 O1 -174.7(3) . . . . ?
C13 C14 C15 N2 5.1(5) . . . . ?
C13 C16 C17 C18 177.5(3) . . . . ?
C13 C16 C21 C20 -178.1(3) . . . . ?
C14 C13 C16 C17 -121.2(4) . . . . ?
C14 C13 C16 C21 57.8(5) . . . . ?
C15 N2 C9 C8 177.6(3) . . . . ?
C15 N2 C9 C10 -1.5(5) . . . . ?
C16 C13 C14 C15 175.3(3) . . . . ?
C16 C13 C14 C23 -1.6(5) . . . . ?
C16 C17 C18 C19 0.5(6) . . . . ?
C17 C16 C21 C20 0.9(5) . . . . ?
C17 C18 C19 C20 1.1(5) . . . . ?
C17 C18 C19 C22 -178.5(3) . . . . ?
C18 C19 C20 C21 -1.7(6) . . . . ?
C19 C20 C21 C16 0.7(6) . . . . ?
C21 C16 C17 C18 -1.6(5) . . . . ?
C22 C19 C20 C21 177.9(4) . . . . ?
C23 C14 C15 O1 2.3(5) . . . . ?
C23 C14 C15 N2 -177.9(3) . . . . ?
C24 O1 C15 N2 -6.7(4) . . . . ?
C24 O1 C15 C14 173.1(3) . . . . ?
N4 C25 C26 C27 -179.2(3) . . . . ?
N4 C25 C30 C29 178.8(3) . . . . ?
N4 C25 C30 C31 -1.0(4) . . . . ?
N4 C32 C33 N5 -5.9(5) . . . . ?
N4 C32 C33 C34 173.6(3) . . . . ?
N5 C33 C34 C35 174.8(3) . . . . ?
N5 C33 C34 C37 -1.8(5) . . . . ?
C25 N4 C32 C31 -0.1(4) . . . . ?
C25 N4 C32 C33 178.3(3) . . . . ?
C25 C26 C27 C28 0.3(5) . . . . ?
C25 C30 C31 C32 1.0(4) . . . . ?
C25 C30 C31 C36 -172.4(4) . . . . ?
C26 C25 C30 C29 -1.2(5) . . . . ?
C26 C25 C30 C31 179.0(3) . . . . ?
C26 C27 C28 C29 -0.8(6) . . . . ?
C27 C28 C29 C30 0.3(6) . . . . ?
C28 C29 C30 C25 0.7(5) . . . . ?
C28 C29 C30 C31 -179.6(4) . . . . ?
C29 C30 C31 C32 -178.8(4) . . . . ?
C29 C30 C31 C36 7.9(7) . . . . ?
C30 C25 C26 C27 0.7(5) . . . . ?
C30 C31 C32 N4 -0.5(4) . . . . ?
C30 C31 C32 C33 -178.9(3) . . . . ?
C30 C31 C36 C35 -159.2(4) . . . . ?
C31 C32 C33 N5 172.2(3) . . . . ?
C31 C32 C33 C34 -8.2(5) . . . . ?
C32 N4 C25 C26 -179.4(4) . . . . ?
C32 N4 C25 C30 0.7(4) . . . . ?
C32 C31 C36 C35 28.2(5) . . . . ?
C32 C33 C34 C35 -4.7(5) . . . . ?
C32 C33 C34 C37 178.7(3) . . . . ?
C33 N5 C39 O2 -177.8(3) . . . . ?
C33 N5 C39 C38 1.4(5) . . . . ?
C33 C34 C35 C36 29.1(5) . . . . ?
C33 C34 C37 C38 0.1(5) . . . . ?
C33 C34 C37 C40 177.7(3) . . . . ?
C34 C35 C36 C31 -39.5(4) . . . . ?
C34 C37 C38 C39 2.1(5) . . . . ?
C34 C37 C38 C47 175.9(3) . . . . ?
C34 C37 C40 C41 -52.1(5) . . . . ?
C34 C37 C40 C45 129.7(4) . . . . ?
C35 C34 C37 C38 -176.2(3) . . . . ?
C35 C34 C37 C40 1.4(5) . . . . ?
C36 C31 C32 N4 173.9(3) . . . . ?
C36 C31 C32 C33 -4.5(5) . . . . ?
C37 C34 C35 C36 -154.6(3) . . . . ?
C37 C38 C39 O2 176.3(3) . . . . ?
C37 C38 C39 N5 -3.0(5) . . . . ?
C37 C40 C41 C42 -179.3(3) . . . . ?
C37 C40 C45 C44 178.8(3) . . . . ?
C38 C37 C40 C41 125.5(4) . . . . ?
C38 C37 C40 C45 -52.7(5) . . . . ?
C39 N5 C33 C32 -179.5(3) . . . . ?
C39 N5 C33 C34 1.0(5) . . . . ?
C40 C37 C38 C39 -175.6(3) . . . . ?
C40 C37 C38 C47 -1.8(5) . . . . ?
C40 C41 C42 C43 1.0(6) . . . . ?
C41 C40 C45 C44 0.5(5) . . . . ?
C41 C42 C43 C44 -0.4(5) . . . . ?
C41 C42 C43 C46 -179.5(3) . . . . ?
C42 C43 C44 C45 -0.1(5) . . . . ?
C43 C44 C45 C40 0.1(5) . . . . ?
C45 C40 C41 C42 -1.1(5) . . . . ?
C46 C43 C44 C45 178.9(3) . . . . ?
C47 C38 C39 O2 2.1(5) . . . . ?
C47 C38 C39 N5 -177.1(3) . . . . ?
C48 O2 C39 N5 6.2(4) . . . . ?
C48 O2 C39 C38 -173.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_5a
_database_code_depnum_ccdc_archive 'CCDC 1498651'
_audit_update_record             
;
2016-08-10 deposited with the CCDC.
2017-06-28 downloaded from the CCDC.
;
_audit_creation_date             2015-11-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C24 H19 N3 O'
_chemical_formula_sum            'C24 H19 N3 O'
_chemical_formula_weight         365.42
_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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.0881(4)
_cell_length_b                   15.1974(6)
_cell_length_c                   12.2090(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.801(3)
_cell_angle_gamma                90
_cell_volume                     1849.76(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4908
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.87
_cell_measurement_theta_min      2.44
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6617
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0492 before and 0.0423 after correction.
The Ratio of minimum to maximum transmission is 0.8875.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.33
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16608
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.912
_diffrn_reflns_theta_min         2.043
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3526
_reflns_number_total             4404
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         4404
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0408
_refine_ls_restrained_S_all      1.040
_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)+(0.0502P)²+0.5731P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1072
_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 Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.04024(9) 0.53330(6) 0.28283(7) 0.0222(2) Uani 1 1 d . . . . .
N1 N 0.82343(11) 0.73915(7) -0.01473(10) 0.0198(2) Uani 1 1 d . . . . .
N2 N 0.92701(10) 0.59146(7) 0.12060(9) 0.0182(2) Uani 1 1 d . . . . .
N3 N 1.00390(11) 0.31701(7) 0.30110(10) 0.0252(3) Uani 1 1 d . . . . .
C1 C 0.76369(12) 0.78977(8) -0.10198(11) 0.0200(3) Uani 1 1 d . . . . .
C2 C 0.75578(13) 0.88196(9) -0.11098(12) 0.0238(3) Uani 1 1 d . . . . .
C3 C 0.68631(13) 0.91412(9) -0.20961(12) 0.0267(3) Uani 1 1 d . . . . .
H3 H 0.6777 0.9747 -0.2187 0.032 Uiso 1 1 calc R . . . .
C4 C 0.62841(13) 0.85919(9) -0.29633(12) 0.0267(3) Uani 1 1 d . . . . .
H4 H 0.5844 0.8841 -0.3615 0.032 Uiso 1 1 calc R . . . .
C5 C 0.63559(13) 0.76905(9) -0.28661(11) 0.0238(3) Uani 1 1 d . . . . .
H5 H 0.5973 0.7328 -0.3443 0.029 Uiso 1 1 calc R . . . .
C6 C 0.70245(12) 0.73310(9) -0.18693(11) 0.0203(3) Uani 1 1 d . . . . .
C7 C 0.72259(12) 0.64549(8) -0.14561(11) 0.0198(3) Uani 1 1 d . . . . .
C8 C 0.79622(12) 0.65216(8) -0.04181(11) 0.0185(3) Uani 1 1 d . . . . .
C9 C 0.83822(12) 0.57755(8) 0.02789(10) 0.0175(2) Uani 1 1 d . . . . .
C10 C 0.77952(12) 0.49549(8) -0.00401(10) 0.0187(3) Uani 1 1 d . . . . .
C11 C 0.66802(13) 0.49151(8) -0.10297(11) 0.0232(3) Uani 1 1 d . . . . .
H11A H 0.5830 0.5019 -0.0773 0.028 Uiso 1 1 calc R . . . .
H11B H 0.6652 0.4326 -0.1339 0.028 Uiso 1 1 calc R . . . .
C12 C 0.68270(13) 0.55756(9) -0.19496(11) 0.0228(3) Uani 1 1 d . . . . .
H12A H 0.7502 0.5370 -0.2376 0.027 Uiso 1 1 calc R . . . .
H12B H 0.5983 0.5627 -0.2446 0.027 Uiso 1 1 calc R . . . .
C13 C 0.81706(12) 0.42348(8) 0.06456(10) 0.0180(3) Uani 1 1 d . . . . .
C14 C 0.91076(12) 0.43714(8) 0.16093(10) 0.0184(3) Uani 1 1 d . . . . .
C15 C 0.95866(12) 0.52316(8) 0.18580(10) 0.0184(3) Uani 1 1 d . . . . .
C16 C 0.81837(16) 0.93998(9) -0.01902(13) 0.0337(3) Uani 1 1 d . . . . .
H16A H 0.7756 0.9305 0.0450 0.050 Uiso 1 1 calc GR . . . .
H16B H 0.8077 1.0004 -0.0416 0.050 Uiso 1 1 calc GR . . . .
H16C H 0.9122 0.9265 -0.0012 0.050 Uiso 1 1 calc GR . . . .
C17 C 0.75499(12) 0.33478(8) 0.04063(10) 0.0182(3) Uani 1 1 d . . . . .
C18 C 0.65513(13) 0.30538(9) 0.09930(12) 0.0238(3) Uani 1 1 d . . . . .
H18 H 0.6298 0.3402 0.1552 0.029 Uiso 1 1 calc R . . . .
C19 C 0.59317(13) 0.22445(9) 0.07481(12) 0.0258(3) Uani 1 1 d . . . . .
H19 H 0.5275 0.2050 0.1148 0.031 Uiso 1 1 calc R . . . .
C20 C 0.62964(13) 0.17316(8) -0.00916(11) 0.0236(3) Uani 1 1 d . . . . .
H20 H 0.5873 0.1195 -0.0265 0.028 Uiso 1 1 calc R . . . .
C21 C 0.72897(13) 0.20142(8) -0.06748(11) 0.0232(3) Uani 1 1 d . . . . .
H21 H 0.7534 0.1665 -0.1237 0.028 Uiso 1 1 calc R . . . .
C22 C 0.79246(13) 0.28169(8) -0.04247(11) 0.0210(3) Uani 1 1 d . . . . .
H22 H 0.8600 0.3000 -0.0813 0.025 Uiso 1 1 calc R . . . .
C23 C 0.95953(12) 0.36810(8) 0.23636(11) 0.0199(3) Uani 1 1 d . . . . .
C24 C 1.08201(14) 0.62217(9) 0.31263(12) 0.0263(3) Uani 1 1 d . . . . .
H24A H 1.1437 0.6420 0.2654 0.039 Uiso 1 1 calc GR . . . .
H24B H 1.1251 0.6235 0.3884 0.039 Uiso 1 1 calc GR . . . .
H24C H 1.0050 0.6601 0.3039 0.039 Uiso 1 1 calc GR . . . .
H1 H 0.8644(16) 0.7566(11) 0.0478(15) 0.031(4) 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
O1 C15 1.3439(15) . ?
O1 C24 1.4447(15) . ?
N1 C1 1.3761(16) . ?
N1 C8 1.3800(16) . ?
N1 H1 0.853(18) . ?
N2 C9 1.3483(16) . ?
N2 C15 1.3173(16) . ?
N3 C23 1.1489(17) . ?
C1 C2 1.4066(18) . ?
C1 C6 1.4153(18) . ?
C2 C3 1.3863(19) . ?
C2 C16 1.490(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.403(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.376(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.4082(18) . ?
C6 C7 1.4273(18) . ?
C7 C8 1.3712(18) . ?
C7 C12 1.4954(18) . ?
C8 C9 1.4418(17) . ?
C9 C10 1.4096(17) . ?
C10 C11 1.5208(17) . ?
C10 C13 1.3946(17) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.5303(18) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.4074(18) . ?
C13 C17 1.4962(16) . ?
C14 C15 1.4106(17) . ?
C14 C23 1.4325(17) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.3958(18) . ?
C17 C22 1.3930(17) . ?
C18 H18 0.9300 . ?
C18 C19 1.3911(18) . ?
C19 H19 0.9300 . ?
C19 C20 1.3818(19) . ?
C20 H20 0.9300 . ?
C20 C21 1.3834(19) . ?
C21 H21 0.9300 . ?
C21 C22 1.3900(18) . ?
C22 H22 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

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
C15 O1 C24 116.42(10) . . ?
C1 N1 C8 107.62(11) . . ?
C1 N1 H1 127.8(11) . . ?
C8 N1 H1 124.3(11) . . ?
C15 N2 C9 116.89(10) . . ?
N1 C1 C2 129.07(13) . . ?
N1 C1 C6 108.51(11) . . ?
C2 C1 C6 122.39(12) . . ?
C1 C2 C16 121.21(13) . . ?
C3 C2 C1 115.73(13) . . ?
C3 C2 C16 123.06(12) . . ?
C2 C3 H3 118.6 . . ?
C2 C3 C4 122.84(13) . . ?
C4 C3 H3 118.6 . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.12(13) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 120.9 . . ?
C4 C5 C6 118.21(13) . . ?
C6 C5 H5 120.9 . . ?
C1 C6 C7 106.62(11) . . ?
C5 C6 C1 119.66(12) . . ?
C5 C6 C7 133.69(13) . . ?
C6 C7 C12 132.55(12) . . ?
C8 C7 C6 106.58(11) . . ?
C8 C7 C12 120.85(11) . . ?
N1 C8 C9 125.61(11) . . ?
C7 C8 N1 110.61(11) . . ?
C7 C8 C9 123.78(11) . . ?
N2 C9 C8 118.01(11) . . ?
N2 C9 C10 124.58(11) . . ?
C10 C9 C8 117.37(11) . . ?
C9 C10 C11 118.88(11) . . ?
C13 C10 C9 117.67(11) . . ?
C13 C10 C11 123.07(11) . . ?
C10 C11 H11A 108.6 . . ?
C10 C11 H11B 108.6 . . ?
C10 C11 C12 114.46(10) . . ?
H11A C11 H11B 107.6 . . ?
C12 C11 H11A 108.6 . . ?
C12 C11 H11B 108.6 . . ?
C7 C12 C11 109.93(11) . . ?
C7 C12 H12A 109.7 . . ?
C7 C12 H12B 109.7 . . ?
C11 C12 H12A 109.7 . . ?
C11 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
C10 C13 C14 118.17(11) . . ?
C10 C13 C17 121.52(11) . . ?
C14 C13 C17 120.24(11) . . ?
C13 C14 C15 118.74(11) . . ?
C13 C14 C23 123.38(11) . . ?
C15 C14 C23 117.89(11) . . ?
O1 C15 C14 116.07(11) . . ?
N2 C15 O1 120.10(11) . . ?
N2 C15 C14 123.83(11) . . ?
C2 C16 H16A 109.5 . . ?
C2 C16 H16B 109.5 . . ?
C2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C13 120.10(11) . . ?
C22 C17 C13 120.79(11) . . ?
C22 C17 C18 119.08(11) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.56(12) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.76(12) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.18(12) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.34(12) . . ?
C22 C21 H21 119.8 . . ?
C17 C22 H22 120.0 . . ?
C21 C22 C17 120.07(12) . . ?
C21 C22 H22 120.0 . . ?
N3 C23 C14 175.30(13) . . ?
O1 C24 H24A 109.5 . . ?
O1 C24 H24B 109.5 . . ?
O1 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

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
N1 C1 C2 C3 -178.96(12) . . . . ?
N1 C1 C2 C16 0.8(2) . . . . ?
N1 C1 C6 C5 -179.12(11) . . . . ?
N1 C1 C6 C7 2.45(13) . . . . ?
N1 C8 C9 N2 -9.97(18) . . . . ?
N1 C8 C9 C10 167.83(11) . . . . ?
N2 C9 C10 C11 172.44(11) . . . . ?
N2 C9 C10 C13 -0.72(18) . . . . ?
C1 N1 C8 C7 1.27(14) . . . . ?
C1 N1 C8 C9 -178.73(11) . . . . ?
C1 C2 C3 C4 -0.77(19) . . . . ?
C1 C6 C7 C8 -1.65(13) . . . . ?
C1 C6 C7 C12 -179.86(13) . . . . ?
C2 C1 C6 C5 2.78(18) . . . . ?
C2 C1 C6 C7 -175.65(11) . . . . ?
C2 C3 C4 C5 1.3(2) . . . . ?
C3 C4 C5 C6 0.18(19) . . . . ?
C4 C5 C6 C1 -2.14(18) . . . . ?
C4 C5 C6 C7 175.78(13) . . . . ?
C5 C6 C7 C8 -179.76(13) . . . . ?
C5 C6 C7 C12 2.0(2) . . . . ?
C6 C1 C2 C3 -1.29(18) . . . . ?
C6 C1 C2 C16 178.46(12) . . . . ?
C6 C7 C8 N1 0.27(14) . . . . ?
C6 C7 C8 C9 -179.74(11) . . . . ?
C6 C7 C12 C11 -152.85(13) . . . . ?
C7 C8 C9 N2 170.04(12) . . . . ?
C7 C8 C9 C10 -12.16(18) . . . . ?
C8 N1 C1 C2 175.63(12) . . . . ?
C8 N1 C1 C6 -2.30(13) . . . . ?
C8 C7 C12 C11 29.14(16) . . . . ?
C8 C9 C10 C11 -5.20(17) . . . . ?
C8 C9 C10 C13 -178.36(11) . . . . ?
C9 N2 C15 O1 -175.99(11) . . . . ?
C9 N2 C15 C14 3.46(18) . . . . ?
C9 C10 C11 C12 33.93(16) . . . . ?
C9 C10 C13 C14 0.01(17) . . . . ?
C9 C10 C13 C17 176.84(11) . . . . ?
C10 C11 C12 C7 -43.83(15) . . . . ?
C10 C13 C14 C15 2.22(17) . . . . ?
C10 C13 C14 C23 -178.44(11) . . . . ?
C10 C13 C17 C18 -101.43(15) . . . . ?
C10 C13 C17 C22 76.47(16) . . . . ?
C11 C10 C13 C14 -172.84(11) . . . . ?
C11 C10 C13 C17 3.99(18) . . . . ?
C12 C7 C8 N1 178.74(11) . . . . ?
C12 C7 C8 C9 -1.27(19) . . . . ?
C13 C10 C11 C12 -153.31(12) . . . . ?
C13 C14 C15 O1 175.29(10) . . . . ?
C13 C14 C15 N2 -4.19(18) . . . . ?
C13 C17 C18 C19 177.54(12) . . . . ?
C13 C17 C22 C21 -176.71(11) . . . . ?
C14 C13 C17 C18 75.33(16) . . . . ?
C14 C13 C17 C22 -106.77(14) . . . . ?
C15 N2 C9 C8 176.65(11) . . . . ?
C15 N2 C9 C10 -0.97(18) . . . . ?
C16 C2 C3 C4 179.50(13) . . . . ?
C17 C13 C14 C15 -174.65(11) . . . . ?
C17 C13 C14 C23 4.69(18) . . . . ?
C17 C18 C19 C20 -0.7(2) . . . . ?
C18 C17 C22 C21 1.21(19) . . . . ?
C18 C19 C20 C21 1.1(2) . . . . ?
C19 C20 C21 C22 -0.3(2) . . . . ?
C20 C21 C22 C17 -0.89(19) . . . . ?
C22 C17 C18 C19 -0.40(19) . . . . ?
C23 C14 C15 O1 -4.08(17) . . . . ?
C23 C14 C15 N2 176.45(11) . . . . ?
C24 O1 C15 N2 3.79(16) . . . . ?
C24 O1 C15 C14 -175.71(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_5h
_database_code_depnum_ccdc_archive 'CCDC 1498653'
_audit_update_record             
;
2016-08-10 deposited with the CCDC.
2017-06-28 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT930_5h                  
;
PROBLEM: Check Twin Law ( 0 0  1)[ 0 0  1] Estimated BASF       0.20
RESPONSE: Probably slight weak twinning detected in original data, which resulted in slightly high wR2, residual peak and second WGHT parameter.  However integration of two components did not give a good refinement.  Testing the twin law resulted in a BASF that refined to essentially zero.
;
# Added during the CSD deposition process: Wednesday 10 August 2016 03:58 PM
# end Validation Reply Form

_audit_creation_date             2016-05-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C21 H15 N3 O S'
_chemical_formula_sum            'C21 H15 N3 O S'
_chemical_formula_weight         357.42
_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'
S S 0.1246 0.1234 '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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.7239(11)
_cell_length_b                   15.4965(15)
_cell_length_c                   10.3257(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.507(8)
_cell_angle_gamma                90
_cell_volume                     1715.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1675
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.00
_cell_measurement_theta_min      2.31
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6397
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0811 before and 0.0612 after correction.
The Ratio of minimum to maximum transmission is 0.8580.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.09
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0760
_diffrn_reflns_av_unetI/netI     0.0697
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13590
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         1.900
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2434
_reflns_number_total             3492
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.766
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.108
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3492
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1173
_refine_ls_R_factor_gt           0.0857
_refine_ls_restrained_S_all      1.161
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0849P)²+8.0978P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2348
_refine_ls_wR_factor_ref         0.2495
_refine_special_details          
;
Probably slight twinning resulting in slightly high wR2, residual peak
and second WGHT parameter. Twin law -1 0 0 0 -1 0 0 0 1 was checked but 
BASF refined to essentially 0.  However refinement is stable and unambigous.
;
_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 Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C15(H15), C19(H19), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
S1 S 0.11465(12) 0.66538(8) 1.07470(14) 0.0252(4) Uani 1 1 d . . . . .
O1 O 0.5411(3) 0.4677(2) 1.2901(4) 0.0238(8) Uani 1 1 d . . . . .
N1 N 0.4178(4) 0.3953(3) 1.1380(4) 0.0169(9) Uani 1 1 d . . . . .
N2 N 0.3132(4) 0.2402(3) 1.0268(4) 0.0170(9) Uani 1 1 d . . . . .
N3 N 0.5040(4) 0.6814(3) 1.2716(5) 0.0251(10) Uani 1 1 d . . . . .
C1 C 0.4561(4) 0.4679(3) 1.1916(5) 0.0171(10) Uani 1 1 d . . . . .
C2 C 0.4116(4) 0.5495(3) 1.1529(5) 0.0173(10) Uani 1 1 d . . . . .
C3 C 0.3179(4) 0.5550(3) 1.0552(5) 0.0162(10) Uani 1 1 d . . . . .
C4 C 0.2755(4) 0.4786(3) 0.9979(5) 0.0157(10) Uani 1 1 d . . . . .
C5 C 0.3299(4) 0.4006(3) 1.0420(5) 0.0151(10) Uani 1 1 d . . . . .
C6 C 0.2852(4) 0.3219(3) 0.9835(5) 0.0156(10) Uani 1 1 d . . . . .
C7 C 0.2092(4) 0.3187(3) 0.8750(5) 0.0165(10) Uani 1 1 d . . . . .
C8 C 0.1776(5) 0.4002(3) 0.8024(5) 0.0187(10) Uani 1 1 d . . . . .
H8A H 0.0966 0.3932 0.7554 0.022 Uiso 1 1 calc R . . . .
H8B H 0.2423 0.4119 0.7380 0.022 Uiso 1 1 calc R . . . .
C9 C 0.1703(5) 0.4756(3) 0.8968(5) 0.0190(11) Uani 1 1 d . . . . .
H9A H 0.1706 0.5301 0.8468 0.023 Uiso 1 1 calc R . . . .
H9B H 0.0900 0.4724 0.9417 0.023 Uiso 1 1 calc R . . . .
C10 C 0.1858(4) 0.2292(3) 0.8493(5) 0.0184(10) Uani 1 1 d . . . . .
C11 C 0.2519(4) 0.1826(3) 0.9468(5) 0.0177(10) Uani 1 1 d . . . . .
C12 C 0.2495(5) 0.0923(3) 0.9517(5) 0.0212(11) Uani 1 1 d . . . . .
H12 H 0.2954 0.0612 1.0164 0.025 Uiso 1 1 calc R . . . .
C13 C 0.1777(5) 0.0504(3) 0.8590(5) 0.0256(12) Uani 1 1 d . . . . .
H13 H 0.1743 -0.0108 0.8598 0.031 Uiso 1 1 calc R . . . .
C14 C 0.1088(5) 0.0959(3) 0.7628(5) 0.0243(12) Uani 1 1 d . . . . .
H14 H 0.0585 0.0648 0.7018 0.029 Uiso 1 1 calc R . . . .
C15 C 0.1132(5) 0.1846(3) 0.7555(5) 0.0211(11) Uani 1 1 d . . . . .
H15 H 0.0685 0.2148 0.6891 0.025 Uiso 1 1 calc R . . . .
C16 C 0.5746(5) 0.3861(3) 1.3473(6) 0.0266(12) Uani 1 1 d . . . . .
H16A H 0.6439 0.3608 1.3002 0.040 Uiso 1 1 calc GR . . . .
H16B H 0.5027 0.3471 1.3424 0.040 Uiso 1 1 calc GR . . . .
H16C H 0.6001 0.3948 1.4382 0.040 Uiso 1 1 calc GR . . . .
C17 C 0.4597(4) 0.6241(3) 1.2176(5) 0.0182(10) Uani 1 1 d . . . . .
C18 C 0.2613(5) 0.6396(3) 1.0230(5) 0.0174(10) Uani 1 1 d . . . . .
C19 C 0.3109(5) 0.7065(3) 0.9552(5) 0.0209(11) Uani 1 1 d . . . . .
H19 H 0.3917 0.7053 0.9197 0.025 Uiso 1 1 calc R . . . .
C20 C 0.2286(5) 0.7778(3) 0.9437(5) 0.0210(11) Uani 1 1 d . . . . .
H20 H 0.2481 0.8290 0.8980 0.025 Uiso 1 1 calc R . . . .
C21 C 0.1194(5) 0.7656(3) 1.0043(5) 0.0231(11) Uani 1 1 d . . . . .
H21 H 0.0543 0.8071 1.0074 0.028 Uiso 1 1 calc R . . . .
H2 H 0.362(6) 0.228(4) 1.100(6) 0.024(15) 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
S1 C18 1.721(5) . ?
S1 C21 1.717(5) . ?
O1 C1 1.347(6) . ?
O1 C16 1.437(6) . ?
N1 C1 1.315(6) . ?
N1 C5 1.353(6) . ?
N2 C6 1.374(6) . ?
N2 C11 1.372(6) . ?
N2 H2 0.92(6) . ?
N3 C17 1.145(7) . ?
C1 C2 1.407(7) . ?
C2 C3 1.408(7) . ?
C2 C17 1.425(7) . ?
C3 C4 1.394(7) . ?
C3 C18 1.479(7) . ?
C4 C5 1.413(7) . ?
C4 C9 1.517(7) . ?
C5 C6 1.438(6) . ?
C6 C7 1.368(7) . ?
C7 C8 1.503(7) . ?
C7 C10 1.433(7) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.526(7) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.413(7) . ?
C10 C15 1.408(7) . ?
C11 C12 1.401(7) . ?
C12 H12 0.9500 . ?
C12 C13 1.375(7) . ?
C13 H13 0.9500 . ?
C13 C14 1.411(8) . ?
C14 H14 0.9500 . ?
C14 C15 1.377(7) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C18 C19 1.366(7) . ?
C19 H19 0.9500 . ?
C19 C20 1.417(7) . ?
C20 H20 0.9500 . ?
C20 C21 1.355(7) . ?
C21 H21 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
C21 S1 C18 92.4(3) . . ?
C1 O1 C16 117.9(4) . . ?
C1 N1 C5 117.4(4) . . ?
C6 N2 H2 124(4) . . ?
C11 N2 C6 107.8(4) . . ?
C11 N2 H2 128(4) . . ?
O1 C1 C2 115.7(4) . . ?
N1 C1 O1 120.9(4) . . ?
N1 C1 C2 123.4(4) . . ?
C1 C2 C3 119.2(4) . . ?
C1 C2 C17 118.7(4) . . ?
C3 C2 C17 122.0(4) . . ?
C2 C3 C18 119.7(4) . . ?
C4 C3 C2 118.2(4) . . ?
C4 C3 C18 122.0(4) . . ?
C3 C4 C5 117.5(4) . . ?
C3 C4 C9 123.1(4) . . ?
C5 C4 C9 119.3(4) . . ?
N1 C5 C4 124.2(4) . . ?
N1 C5 C6 118.3(4) . . ?
C4 C5 C6 117.4(4) . . ?
N2 C6 C5 125.3(4) . . ?
C7 C6 N2 110.7(4) . . ?
C7 C6 C5 124.0(4) . . ?
C6 C7 C8 119.9(4) . . ?
C6 C7 C10 106.5(4) . . ?
C10 C7 C8 133.2(4) . . ?
C7 C8 H8A 109.7 . . ?
C7 C8 H8B 109.7 . . ?
C7 C8 C9 109.9(4) . . ?
H8A C8 H8B 108.2 . . ?
C9 C8 H8A 109.7 . . ?
C9 C8 H8B 109.7 . . ?
C4 C9 C8 114.4(4) . . ?
C4 C9 H9A 108.7 . . ?
C4 C9 H9B 108.7 . . ?
C8 C9 H9A 108.7 . . ?
C8 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C11 C10 C7 106.3(4) . . ?
C15 C10 C7 133.9(5) . . ?
C15 C10 C11 119.8(5) . . ?
N2 C11 C10 108.7(4) . . ?
N2 C11 C12 129.5(5) . . ?
C12 C11 C10 121.8(5) . . ?
C11 C12 H12 121.4 . . ?
C13 C12 C11 117.2(5) . . ?
C13 C12 H12 121.4 . . ?
C12 C13 H13 119.1 . . ?
C12 C13 C14 121.8(5) . . ?
C14 C13 H13 119.1 . . ?
C13 C14 H14 119.4 . . ?
C15 C14 C13 121.3(5) . . ?
C15 C14 H14 119.4 . . ?
C10 C15 H15 120.9 . . ?
C14 C15 C10 118.1(5) . . ?
C14 C15 H15 120.9 . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N3 C17 C2 176.2(5) . . ?
C3 C18 S1 120.6(4) . . ?
C19 C18 S1 110.7(4) . . ?
C19 C18 C3 128.6(5) . . ?
C18 C19 H19 123.7 . . ?
C18 C19 C20 112.6(5) . . ?
C20 C19 H19 123.7 . . ?
C19 C20 H20 123.3 . . ?
C21 C20 C19 113.4(5) . . ?
C21 C20 H20 123.3 . . ?
S1 C21 H21 124.5 . . ?
C20 C21 S1 110.9(4) . . ?
C20 C21 H21 124.5 . . ?

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
S1 C18 C19 C20 -1.0(6) . . . . ?
O1 C1 C2 C3 -176.7(4) . . . . ?
O1 C1 C2 C17 0.9(7) . . . . ?
N1 C1 C2 C3 2.4(8) . . . . ?
N1 C1 C2 C17 -179.9(5) . . . . ?
N1 C5 C6 N2 8.1(7) . . . . ?
N1 C5 C6 C7 -171.1(4) . . . . ?
N2 C6 C7 C8 -173.4(4) . . . . ?
N2 C6 C7 C10 1.1(6) . . . . ?
N2 C11 C12 C13 179.1(5) . . . . ?
C1 N1 C5 C4 -1.3(7) . . . . ?
C1 N1 C5 C6 -179.0(4) . . . . ?
C1 C2 C3 C4 -1.8(7) . . . . ?
C1 C2 C3 C18 173.8(4) . . . . ?
C2 C3 C4 C5 -0.1(7) . . . . ?
C2 C3 C4 C9 176.7(4) . . . . ?
C2 C3 C18 S1 -104.0(5) . . . . ?
C2 C3 C18 C19 74.9(7) . . . . ?
C3 C4 C5 N1 1.8(7) . . . . ?
C3 C4 C5 C6 179.5(4) . . . . ?
C3 C4 C9 C8 152.1(5) . . . . ?
C3 C18 C19 C20 -180.0(5) . . . . ?
C4 C3 C18 S1 71.5(6) . . . . ?
C4 C3 C18 C19 -109.6(6) . . . . ?
C4 C5 C6 N2 -169.7(5) . . . . ?
C4 C5 C6 C7 11.1(7) . . . . ?
C5 N1 C1 O1 178.3(4) . . . . ?
C5 N1 C1 C2 -0.8(7) . . . . ?
C5 C4 C9 C8 -31.2(6) . . . . ?
C5 C6 C7 C8 5.9(7) . . . . ?
C5 C6 C7 C10 -179.6(4) . . . . ?
C6 N2 C11 C10 1.3(5) . . . . ?
C6 N2 C11 C12 -179.1(5) . . . . ?
C6 C7 C8 C9 -33.3(6) . . . . ?
C6 C7 C10 C11 -0.3(5) . . . . ?
C6 C7 C10 C15 177.8(5) . . . . ?
C7 C8 C9 C4 44.4(6) . . . . ?
C7 C10 C11 N2 -0.6(5) . . . . ?
C7 C10 C11 C12 179.7(5) . . . . ?
C7 C10 C15 C14 -177.6(5) . . . . ?
C8 C7 C10 C11 173.2(5) . . . . ?
C8 C7 C10 C15 -8.7(10) . . . . ?
C9 C4 C5 N1 -175.1(4) . . . . ?
C9 C4 C5 C6 2.6(7) . . . . ?
C10 C7 C8 C9 154.0(5) . . . . ?
C10 C11 C12 C13 -1.4(8) . . . . ?
C11 N2 C6 C5 179.2(5) . . . . ?
C11 N2 C6 C7 -1.5(6) . . . . ?
C11 C10 C15 C14 0.3(7) . . . . ?
C11 C12 C13 C14 -0.1(8) . . . . ?
C12 C13 C14 C15 1.7(8) . . . . ?
C13 C14 C15 C10 -1.8(8) . . . . ?
C15 C10 C11 N2 -179.0(4) . . . . ?
C15 C10 C11 C12 1.3(8) . . . . ?
C16 O1 C1 N1 -9.0(7) . . . . ?
C16 O1 C1 C2 170.2(5) . . . . ?
C17 C2 C3 C4 -179.4(5) . . . . ?
C17 C2 C3 C18 -3.8(7) . . . . ?
C18 S1 C21 C20 0.3(4) . . . . ?
C18 C3 C4 C5 -175.6(4) . . . . ?
C18 C3 C4 C9 1.2(7) . . . . ?
C18 C19 C20 C21 1.3(7) . . . . ?
C19 C20 C21 S1 -1.0(6) . . . . ?
C21 S1 C18 C3 179.5(4) . . . . ?
C21 S1 C18 C19 0.4(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_5j
_database_code_depnum_ccdc_archive 'CCDC 1498654'
_audit_update_record             
;
2016-08-10 deposited with the CCDC.
2017-06-28 downloaded from the CCDC.
;
_audit_creation_date             2015-11-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C25 H21 N3 O'
_chemical_formula_sum            'C25 H21 N3 O'
_chemical_formula_weight         379.45
_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                   9.9044(6)
_cell_length_b                   16.2434(9)
_cell_length_c                   12.9264(8)
_cell_angle_alpha                90
_cell_angle_beta                 106.592(4)
_cell_angle_gamma                90
_cell_volume                     1993.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4533
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.85
_cell_measurement_theta_min      2.30
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0528 before and 0.0432 after correction.
The Ratio of minimum to maximum transmission is 0.9254.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17960
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.038
_diffrn_reflns_theta_min         2.067
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3811
_reflns_number_total             4780
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         4780
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0449
_refine_ls_restrained_S_all      1.031
_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)+(0.0576P)²+0.7853P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1220
_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 Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C18(H18), C19(H19), C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C23(H23A,H23B,H23C), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.31577(10) 0.62489(6) 0.79169(8) 0.0209(2) Uani 1 1 d . . . . .
N1 N 0.96919(12) 0.40547(7) 0.61880(10) 0.0187(2) Uani 1 1 d . . . . .
N2 N 1.11686(11) 0.55420(7) 0.69599(9) 0.0162(2) Uani 1 1 d . . . . .
N3 N 1.25441(13) 0.83255(8) 0.78191(11) 0.0281(3) Uani 1 1 d . . . . .
C1 C 0.87159(14) 0.34856(8) 0.56460(11) 0.0177(3) Uani 1 1 d . . . . .
C2 C 0.88120(15) 0.26275(8) 0.56220(12) 0.0226(3) Uani 1 1 d . . . . .
H2 H 0.9623 0.2353 0.6008 0.027 Uiso 1 1 calc R . . . .
C3 C 0.76557(16) 0.22045(9) 0.50031(12) 0.0240(3) Uani 1 1 d . . . . .
H3 H 0.7702 0.1634 0.4972 0.029 Uiso 1 1 calc R . . . .
C4 C 0.64034(15) 0.26021(9) 0.44149(11) 0.0219(3) Uani 1 1 d . . . . .
C5 C 0.63184(14) 0.34547(8) 0.44531(11) 0.0190(3) Uani 1 1 d . . . . .
H5 H 0.5498 0.3723 0.4072 0.023 Uiso 1 1 calc R . . . .
C6 C 0.74766(13) 0.39103(8) 0.50701(10) 0.0161(3) Uani 1 1 d . . . . .
C7 C 0.77447(13) 0.47725(8) 0.52928(10) 0.0158(3) Uani 1 1 d . . . . .
C8 C 0.91031(13) 0.48244(8) 0.59704(10) 0.0159(3) Uani 1 1 d . . . . .
C9 C 0.97904(13) 0.55812(8) 0.63786(10) 0.0154(3) Uani 1 1 d . . . . .
C10 C 0.89764(13) 0.63085(8) 0.61724(10) 0.0162(3) Uani 1 1 d . . . . .
C11 C 0.74245(15) 0.62426(9) 0.56428(13) 0.0258(3) Uani 1 1 d . . . . .
H11A H 0.6954 0.6226 0.6206 0.031 Uiso 1 1 calc R . . . .
H11B H 0.7120 0.6741 0.5229 0.031 Uiso 1 1 calc R . . . .
C12 C 0.69307(14) 0.55303(8) 0.49184(12) 0.0219(3) Uani 1 1 d . . . . .
H12A H 0.5947 0.5428 0.4862 0.026 Uiso 1 1 calc R . . . .
H12B H 0.6995 0.5667 0.4203 0.026 Uiso 1 1 calc R . . . .
C13 C 0.96552(14) 0.70475(8) 0.65830(10) 0.0158(3) Uani 1 1 d . . . . .
C14 C 1.10947(14) 0.70116(8) 0.71538(10) 0.0170(3) Uani 1 1 d . . . . .
C15 C 1.17874(13) 0.62420(8) 0.73255(10) 0.0165(3) Uani 1 1 d . . . . .
C16 C 0.51741(17) 0.20972(10) 0.37610(14) 0.0306(4) Uani 1 1 d . . . . .
H16A H 0.5519 0.1635 0.3448 0.046 Uiso 1 1 calc GR . . . .
H16B H 0.4588 0.2432 0.3197 0.046 Uiso 1 1 calc GR . . . .
H16C H 0.4634 0.1903 0.4222 0.046 Uiso 1 1 calc GR . . . .
C17 C 0.89112(13) 0.78557(8) 0.64788(11) 0.0167(3) Uani 1 1 d . . . . .
C18 C 0.87931(15) 0.82595(8) 0.74039(11) 0.0205(3) Uani 1 1 d . . . . .
H18 H 0.9181 0.8023 0.8079 0.025 Uiso 1 1 calc R . . . .
C19 C 0.81005(15) 0.90113(9) 0.73214(12) 0.0220(3) Uani 1 1 d . . . . .
H19 H 0.8027 0.9270 0.7945 0.026 Uiso 1 1 calc R . . . .
C20 C 0.75147(15) 0.93845(8) 0.63242(12) 0.0206(3) Uani 1 1 d . . . . .
C21 C 0.76501(15) 0.89835(9) 0.54049(11) 0.0217(3) Uani 1 1 d . . . . .
H21 H 0.7277 0.9225 0.4731 0.026 Uiso 1 1 calc R . . . .
C22 C 0.83332(15) 0.82284(8) 0.54788(11) 0.0198(3) Uani 1 1 d . . . . .
H22 H 0.8405 0.7970 0.4855 0.024 Uiso 1 1 calc R . . . .
C23 C 0.67214(18) 1.01853(9) 0.62493(13) 0.0301(3) Uani 1 1 d . . . . .
H23A H 0.5928 1.0110 0.6527 0.045 Uiso 1 1 calc GR . . . .
H23B H 0.6397 1.0356 0.5509 0.045 Uiso 1 1 calc GR . . . .
H23C H 0.7334 1.0599 0.6665 0.045 Uiso 1 1 calc GR . . . .
C24 C 1.18857(14) 0.77447(9) 0.75285(11) 0.0204(3) Uani 1 1 d . . . . .
C25 C 1.38870(15) 0.54696(9) 0.80530(13) 0.0267(3) Uani 1 1 d . . . . .
H25A H 1.3880 0.5256 0.7359 0.040 Uiso 1 1 calc GR . . . .
H25B H 1.3423 0.5088 0.8405 0.040 Uiso 1 1 calc GR . . . .
H25C H 1.4843 0.5546 0.8485 0.040 Uiso 1 1 calc GR . . . .
H1 H 1.055(2) 0.3953(11) 0.6551(14) 0.033(5) 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
O1 C15 1.3542(15) . ?
O1 C25 1.4432(17) . ?
N1 C1 1.3759(17) . ?
N1 C8 1.3743(17) . ?
N1 H1 0.863(19) . ?
N2 C9 1.3588(16) . ?
N2 C15 1.3138(17) . ?
N3 C24 1.1473(18) . ?
C1 C2 1.3980(19) . ?
C1 C6 1.4195(18) . ?
C2 H2 0.9300 . ?
C2 C3 1.378(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.412(2) . ?
C4 C5 1.389(2) . ?
C4 C16 1.511(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.4061(18) . ?
C6 C7 1.4391(18) . ?
C7 C8 1.3826(18) . ?
C7 C12 1.4752(18) . ?
C8 C9 1.4310(18) . ?
C9 C10 1.4121(18) . ?
C10 C11 1.4972(18) . ?
C10 C13 1.4038(18) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.4809(19) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.4070(18) . ?
C13 C17 1.4926(18) . ?
C14 C15 1.4127(18) . ?
C14 C24 1.4318(18) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.3978(18) . ?
C17 C22 1.3938(19) . ?
C18 H18 0.9300 . ?
C18 C19 1.3897(19) . ?
C19 H19 0.9300 . ?
C19 C20 1.392(2) . ?
C20 C21 1.3948(19) . ?
C20 C23 1.5083(19) . ?
C21 H21 0.9300 . ?
C21 C22 1.3907(19) . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

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
C15 O1 C25 116.58(11) . . ?
C1 N1 H1 126.1(12) . . ?
C8 N1 C1 108.16(11) . . ?
C8 N1 H1 125.5(13) . . ?
C15 N2 C9 116.75(11) . . ?
N1 C1 C2 129.70(13) . . ?
N1 C1 C6 108.48(11) . . ?
C2 C1 C6 121.81(12) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 C1 117.34(13) . . ?
C3 C2 H2 121.3 . . ?
C2 C3 H3 118.6 . . ?
C2 C3 C4 122.74(13) . . ?
C4 C3 H3 118.6 . . ?
C3 C4 C16 119.77(13) . . ?
C5 C4 C3 119.30(13) . . ?
C5 C4 C16 120.92(14) . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.80(13) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C7 106.60(11) . . ?
C5 C6 C1 119.00(12) . . ?
C5 C6 C7 134.40(12) . . ?
C6 C7 C12 133.95(12) . . ?
C8 C7 C6 106.06(11) . . ?
C8 C7 C12 119.91(12) . . ?
N1 C8 C7 110.70(11) . . ?
N1 C8 C9 125.21(12) . . ?
C7 C8 C9 124.08(12) . . ?
N2 C9 C8 117.43(11) . . ?
N2 C9 C10 124.95(12) . . ?
C10 C9 C8 117.60(11) . . ?
C9 C10 C11 118.86(11) . . ?
C13 C10 C9 117.26(12) . . ?
C13 C10 C11 123.53(12) . . ?
C10 C11 H11A 108.0 . . ?
C10 C11 H11B 108.0 . . ?
H11A C11 H11B 107.3 . . ?
C12 C11 C10 117.10(12) . . ?
C12 C11 H11A 108.0 . . ?
C12 C11 H11B 108.0 . . ?
C7 C12 C11 113.18(12) . . ?
C7 C12 H12A 108.9 . . ?
C7 C12 H12B 108.9 . . ?
C11 C12 H12A 108.9 . . ?
C11 C12 H12B 108.9 . . ?
H12A C12 H12B 107.8 . . ?
C10 C13 C14 117.84(12) . . ?
C10 C13 C17 123.17(12) . . ?
C14 C13 C17 118.95(11) . . ?
C13 C14 C15 119.54(12) . . ?
C13 C14 C24 121.17(12) . . ?
C15 C14 C24 119.25(12) . . ?
O1 C15 C14 116.41(11) . . ?
N2 C15 O1 119.98(12) . . ?
N2 C15 C14 123.61(12) . . ?
C4 C16 H16A 109.5 . . ?
C4 C16 H16B 109.5 . . ?
C4 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C13 119.69(12) . . ?
C22 C17 C13 121.82(12) . . ?
C22 C17 C18 118.49(12) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.45(13) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 119.3 . . ?
C18 C19 C20 121.32(13) . . ?
C20 C19 H19 119.3 . . ?
C19 C20 C21 117.99(13) . . ?
C19 C20 C23 120.44(13) . . ?
C21 C20 C23 121.54(13) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 C20 121.10(13) . . ?
C22 C21 H21 119.4 . . ?
C17 C22 H22 119.7 . . ?
C21 C22 C17 120.65(12) . . ?
C21 C22 H22 119.7 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N3 C24 C14 178.39(15) . . ?
O1 C25 H25A 109.5 . . ?
O1 C25 H25B 109.5 . . ?
O1 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

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
N1 C1 C2 C3 179.89(13) . . . . ?
N1 C1 C6 C5 -179.74(11) . . . . ?
N1 C1 C6 C7 -0.23(14) . . . . ?
N1 C8 C9 N2 5.31(19) . . . . ?
N1 C8 C9 C10 -173.01(12) . . . . ?
N2 C9 C10 C11 -172.11(12) . . . . ?
N2 C9 C10 C13 1.32(19) . . . . ?
C1 N1 C8 C7 0.21(15) . . . . ?
C1 N1 C8 C9 -179.50(12) . . . . ?
C1 C2 C3 C4 -0.6(2) . . . . ?
C1 C6 C7 C8 0.35(14) . . . . ?
C1 C6 C7 C12 177.05(14) . . . . ?
C2 C1 C6 C5 -0.46(19) . . . . ?
C2 C1 C6 C7 179.06(12) . . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
C2 C3 C4 C16 -179.50(14) . . . . ?
C3 C4 C5 C6 0.27(19) . . . . ?
C4 C5 C6 C1 -0.08(19) . . . . ?
C4 C5 C6 C7 -179.43(14) . . . . ?
C5 C6 C7 C8 179.75(14) . . . . ?
C5 C6 C7 C12 -3.5(3) . . . . ?
C6 C1 C2 C3 0.8(2) . . . . ?
C6 C7 C8 N1 -0.35(15) . . . . ?
C6 C7 C8 C9 179.37(12) . . . . ?
C6 C7 C12 C11 160.11(14) . . . . ?
C7 C8 C9 N2 -174.37(12) . . . . ?
C7 C8 C9 C10 7.31(19) . . . . ?
C8 N1 C1 C2 -179.19(14) . . . . ?
C8 N1 C1 C6 0.02(14) . . . . ?
C8 C7 C12 C11 -23.54(18) . . . . ?
C8 C9 C10 C11 6.07(18) . . . . ?
C8 C9 C10 C13 179.50(11) . . . . ?
C9 N2 C15 O1 179.59(11) . . . . ?
C9 N2 C15 C14 0.67(18) . . . . ?
C9 C10 C11 C12 -28.3(2) . . . . ?
C9 C10 C13 C14 0.89(18) . . . . ?
C9 C10 C13 C17 -176.65(12) . . . . ?
C10 C11 C12 C7 35.88(19) . . . . ?
C10 C13 C14 C15 -2.18(19) . . . . ?
C10 C13 C14 C24 175.37(12) . . . . ?
C10 C13 C17 C18 114.85(15) . . . . ?
C10 C13 C17 C22 -65.66(18) . . . . ?
C11 C10 C13 C14 173.98(13) . . . . ?
C11 C10 C13 C17 -3.6(2) . . . . ?
C12 C7 C8 N1 -177.62(12) . . . . ?
C12 C7 C8 C9 2.1(2) . . . . ?
C13 C10 C11 C12 158.72(13) . . . . ?
C13 C14 C15 O1 -177.50(11) . . . . ?
C13 C14 C15 N2 1.5(2) . . . . ?
C13 C17 C18 C19 -179.83(12) . . . . ?
C13 C17 C22 C21 -179.74(12) . . . . ?
C14 C13 C17 C18 -62.66(17) . . . . ?
C14 C13 C17 C22 116.83(14) . . . . ?
C15 N2 C9 C8 179.71(11) . . . . ?
C15 N2 C9 C10 -2.11(19) . . . . ?
C16 C4 C5 C6 179.83(12) . . . . ?
C17 C13 C14 C15 175.46(11) . . . . ?
C17 C13 C14 C24 -6.99(19) . . . . ?
C17 C18 C19 C20 -0.4(2) . . . . ?
C18 C17 C22 C21 -0.2(2) . . . . ?
C18 C19 C20 C21 -0.4(2) . . . . ?
C18 C19 C20 C23 177.75(13) . . . . ?
C19 C20 C21 C22 0.8(2) . . . . ?
C20 C21 C22 C17 -0.5(2) . . . . ?
C22 C17 C18 C19 0.7(2) . . . . ?
C23 C20 C21 C22 -177.30(13) . . . . ?
C24 C14 C15 O1 4.90(18) . . . . ?
C24 C14 C15 N2 -176.14(12) . . . . ?
C25 O1 C15 N2 3.73(18) . . . . ?
C25 O1 C15 C14 -177.28(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_5d
_database_code_depnum_ccdc_archive 'CCDC 1498652'
_audit_update_record             
;
2016-08-10 deposited with the CCDC.
2017-06-28 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT915_5d                  
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         84 %
RESPONSE: Absolute structure not determined.
;
# Added during the CSD deposition process: Wednesday 10 August 2016 03:58 PM
# end Validation Reply Form

_audit_creation_date             2016-08-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C23 H17 N3 O'
_chemical_formula_sum            'C23 H17 N3 O'
_chemical_formula_weight         351.39
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   13.4283(10)
_cell_length_b                   15.7465(11)
_cell_length_c                   16.5327(11)
_cell_angle_alpha                90
_cell_angle_beta                 92.893(6)
_cell_angle_gamma                90
_cell_volume                     3491.4(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2495
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.27
_cell_measurement_theta_min      2.30
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6852
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0684 before and 0.0572 after correction.
The Ratio of minimum to maximum transmission is 0.9190.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.328
_exptl_crystal_size_mid          0.272
_exptl_crystal_size_min          0.13
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0767
_diffrn_reflns_av_unetI/netI     0.1159
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            28602
_diffrn_reflns_point_group_measured_fraction_full 0.929
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.373
_diffrn_reflns_theta_min         1.233
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.783
_reflns_Friedel_fraction_full    0.853
_reflns_Friedel_fraction_max     0.845
_reflns_number_gt                8541
_reflns_number_total             13203
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     977
_refine_ls_number_reflns         13203
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1143
_refine_ls_R_factor_gt           0.0592
_refine_ls_restrained_S_all      0.993
_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)+(0.0384P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1160
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C54(H54A,H54B), C55(H55A,H55B), C31(H31A,H31B),
 C32(H32A,H32B), C75(H75A,H75B), C76(H76A,H76B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C12(H12), C13(H13), C14(H14), C15(H15), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21), N7(H7), C58(H58), C59(H59), C60(H60), C61(H61), C63(H63),
 C64(H64), C65(H65), C66(H66), C67(H67), N4(H4), C35(H35), C36(H36), C37(H37),
 C38(H38), C40(H40), C41(H41), C42(H42), C43(H43), C44(H44), N10(H10), C81(H81),
  C82(H82), C83(H83), C84(H84), C86(H86), C87(H87), C88(H88), C89(H89), C90(H90)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C69(H69A,H69B,H69C), C46(H46A,H46B,H46C), C92(H92A,H92B,
 H92C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0653(3) 0.3431(2) 0.17978(19) 0.0211(8) Uani 1 1 d . . . . .
N1 N 0.3156(3) 0.1133(3) 0.2338(2) 0.0231(11) Uani 1 1 d . . . . .
H1 H 0.2525 0.1041 0.2193 0.028 Uiso 1 1 calc R . . . .
N2 N 0.2098(3) 0.2684(3) 0.2119(2) 0.0190(10) Uani 1 1 d . . . . .
N3 N 0.1072(3) 0.5543(3) 0.1754(3) 0.0297(12) Uani 1 1 d . . . . .
C1 C 0.3091(4) 0.2714(3) 0.2302(3) 0.0185(12) Uani 1 1 d . . . . .
C2 C 0.3674(4) 0.3461(3) 0.2342(3) 0.0180(12) Uani 1 1 d . . . . .
C3 C 0.3176(4) 0.4224(3) 0.2176(3) 0.0174(12) Uani 1 1 d . . . . .
C4 C 0.2143(4) 0.4200(3) 0.1988(3) 0.0191(12) Uani 1 1 d . . . . .
C5 C 0.1651(4) 0.3414(3) 0.1975(3) 0.0213(12) Uani 1 1 d . . . . .
C6 C 0.3600(4) 0.1919(3) 0.2442(3) 0.0182(12) Uani 1 1 d . . . . .
C7 C 0.4583(4) 0.1833(3) 0.2682(3) 0.0206(13) Uani 1 1 d . . . . .
C8 C 0.5207(4) 0.2596(3) 0.2876(3) 0.0274(13) Uani 1 1 d . . . . .
H8A H 0.5895 0.2493 0.2710 0.033 Uiso 1 1 calc R . . . .
H8B H 0.5236 0.2693 0.3469 0.033 Uiso 1 1 calc R . . . .
C9 C 0.4792(4) 0.3382(3) 0.2448(4) 0.0320(14) Uani 1 1 d . . . . .
H9A H 0.5045 0.3886 0.2751 0.038 Uiso 1 1 calc R . . . .
H9B H 0.5068 0.3406 0.1904 0.038 Uiso 1 1 calc R . . . .
C10 C 0.4776(4) 0.0937(3) 0.2716(3) 0.0204(13) Uani 1 1 d . . . . .
C11 C 0.3860(4) 0.0524(3) 0.2497(3) 0.0189(12) Uani 1 1 d . . . . .
C12 C 0.3779(4) -0.0359(3) 0.2443(3) 0.0245(13) Uani 1 1 d . . . . .
H12 H 0.3165 -0.0627 0.2287 0.029 Uiso 1 1 calc R . . . .
C13 C 0.4634(4) -0.0825(4) 0.2626(3) 0.0274(14) Uani 1 1 d . . . . .
H13 H 0.4603 -0.1427 0.2600 0.033 Uiso 1 1 calc R . . . .
C14 C 0.5543(5) -0.0437(3) 0.2849(3) 0.0294(14) Uani 1 1 d . . . . .
H14 H 0.6113 -0.0780 0.2972 0.035 Uiso 1 1 calc R . . . .
C15 C 0.5627(4) 0.0434(4) 0.2895(3) 0.0273(13) Uani 1 1 d . . . . .
H15 H 0.6249 0.0692 0.3044 0.033 Uiso 1 1 calc R . . . .
C16 C 0.3698(4) 0.5064(3) 0.2167(3) 0.0193(12) Uani 1 1 d . . . . .
C17 C 0.3668(4) 0.5538(3) 0.1457(3) 0.0214(12) Uani 1 1 d . . . . .
H17 H 0.3325 0.5322 0.0984 0.026 Uiso 1 1 calc R . . . .
C18 C 0.4137(4) 0.6326(3) 0.1429(3) 0.0249(13) Uani 1 1 d . . . . .
H18 H 0.4124 0.6641 0.0939 0.030 Uiso 1 1 calc R . . . .
C19 C 0.4623(4) 0.6647(3) 0.2127(3) 0.0256(13) Uani 1 1 d . . . . .
H19 H 0.4937 0.7188 0.2117 0.031 Uiso 1 1 calc R . . . .
C20 C 0.4649(4) 0.6182(3) 0.2831(3) 0.0247(13) Uani 1 1 d . . . . .
H20 H 0.4979 0.6405 0.3306 0.030 Uiso 1 1 calc R . . . .
C21 C 0.4203(4) 0.5397(3) 0.2859(3) 0.0210(12) Uani 1 1 d . . . . .
H21 H 0.4238 0.5079 0.3348 0.025 Uiso 1 1 calc R . . . .
C22 C 0.1560(4) 0.4951(3) 0.1849(3) 0.0194(12) Uani 1 1 d . . . . .
C23 C 0.0118(4) 0.2640(3) 0.1887(3) 0.0255(13) Uani 1 1 d . . . . .
H23A H 0.0405 0.2203 0.1546 0.038 Uiso 1 1 calc GR . . . .
H23B H -0.0586 0.2723 0.1720 0.038 Uiso 1 1 calc GR . . . .
H23C H 0.0174 0.2459 0.2455 0.038 Uiso 1 1 calc GR . . . .
O3 O -0.0401(3) 0.3270(2) 1.0104(2) 0.0243(9) Uani 1 1 d . . . . .
N7 N 0.2041(3) 0.5535(3) 0.9545(2) 0.0216(10) Uani 1 1 d . . . . .
H7 H 0.1409 0.5632 0.9628 0.026 Uiso 1 1 calc R . . . .
N8 N 0.1014(3) 0.3996(3) 0.9798(2) 0.0196(10) Uani 1 1 d . . . . .
N9 N -0.0059(4) 0.1158(3) 1.0076(3) 0.0322(12) Uani 1 1 d . . . . .
C47 C 0.1970(4) 0.3952(3) 0.9585(3) 0.0191(12) Uani 1 1 d . . . . .
C48 C 0.2505(4) 0.3207(3) 0.9458(3) 0.0194(12) Uani 1 1 d . . . . .
C49 C 0.2020(4) 0.2442(3) 0.9603(3) 0.0203(13) Uani 1 1 d . . . . .
C50 C 0.1019(4) 0.2475(3) 0.9831(3) 0.0210(12) Uani 1 1 d . . . . .
C51 C 0.0557(4) 0.3268(3) 0.9909(3) 0.0212(12) Uani 1 1 d . . . . .
C52 C 0.2485(4) 0.4750(3) 0.9484(3) 0.0184(12) Uani 1 1 d . . . . .
C53 C 0.3478(4) 0.4833(3) 0.9371(3) 0.0210(13) Uani 1 1 d . . . . .
C54 C 0.4133(4) 0.4063(3) 0.9401(3) 0.0249(13) Uani 1 1 d . . . . .
H54A H 0.4417 0.3982 0.9961 0.030 Uiso 1 1 calc R . . . .
H54B H 0.4693 0.4147 0.9042 0.030 Uiso 1 1 calc R . . . .
C55 C 0.3543(4) 0.3270(3) 0.9134(3) 0.0239(13) Uani 1 1 d . . . . .
H55A H 0.3480 0.3261 0.8535 0.029 Uiso 1 1 calc R . . . .
H55B H 0.3929 0.2762 0.9311 0.029 Uiso 1 1 calc R . . . .
C56 C 0.3682(4) 0.5725(3) 0.9344(3) 0.0209(13) Uani 1 1 d . . . . .
C57 C 0.2766(4) 0.6136(3) 0.9452(3) 0.0219(13) Uani 1 1 d . . . . .
C58 C 0.2667(5) 0.7028(3) 0.9455(3) 0.0270(14) Uani 1 1 d . . . . .
H58 H 0.2043 0.7300 0.9513 0.032 Uiso 1 1 calc R . . . .
C59 C 0.3532(5) 0.7479(4) 0.9368(3) 0.0315(15) Uani 1 1 d . . . . .
H59 H 0.3503 0.8082 0.9372 0.038 Uiso 1 1 calc R . . . .
C60 C 0.4457(5) 0.7084(3) 0.9275(3) 0.0305(15) Uani 1 1 d . . . . .
H60 H 0.5034 0.7424 0.9223 0.037 Uiso 1 1 calc R . . . .
C61 C 0.4543(4) 0.6208(3) 0.9258(3) 0.0274(13) Uani 1 1 d . . . . .
H61 H 0.5169 0.5943 0.9190 0.033 Uiso 1 1 calc R . . . .
C62 C 0.2519(4) 0.1599(3) 0.9558(3) 0.0189(12) Uani 1 1 d . . . . .
C63 C 0.2554(4) 0.1076(3) 1.0230(3) 0.0257(13) Uani 1 1 d . . . . .
H63 H 0.2250 0.1252 1.0709 0.031 Uiso 1 1 calc R . . . .
C64 C 0.3033(4) 0.0290(3) 1.0209(3) 0.0284(14) Uani 1 1 d . . . . .
H64 H 0.3063 -0.0064 1.0674 0.034 Uiso 1 1 calc R . . . .
C65 C 0.3463(4) 0.0028(4) 0.9508(4) 0.0302(14) Uani 1 1 d . . . . .
H65 H 0.3796 -0.0504 0.9495 0.036 Uiso 1 1 calc R . . . .
C66 C 0.3409(4) 0.0537(3) 0.8828(3) 0.0279(13) Uani 1 1 d . . . . .
H66 H 0.3693 0.0350 0.8344 0.034 Uiso 1 1 calc R . . . .
C67 C 0.2943(4) 0.1318(3) 0.8852(3) 0.0222(13) Uani 1 1 d . . . . .
H67 H 0.2910 0.1668 0.8383 0.027 Uiso 1 1 calc R . . . .
C68 C 0.0442(4) 0.1731(4) 0.9958(3) 0.0249(13) Uani 1 1 d . . . . .
C69 C -0.0849(4) 0.4098(3) 1.0229(3) 0.0285(14) Uani 1 1 d . . . . .
H69A H -0.0879 0.4414 0.9718 0.043 Uiso 1 1 calc GR . . . .
H69B H -0.0444 0.4413 1.0637 0.043 Uiso 1 1 calc GR . . . .
H69C H -0.1524 0.4023 1.0416 0.043 Uiso 1 1 calc GR . . . .
O2 O 0.4610(3) 0.5462(2) 0.5049(2) 0.0231(9) Uani 1 1 d . . . . .
N4 N 0.6940(3) 0.7872(2) 0.5495(2) 0.0192(10) Uani 1 1 d . . . . .
H4 H 0.6316 0.7928 0.5314 0.023 Uiso 1 1 calc R . . . .
N5 N 0.6010(3) 0.6275(2) 0.5336(2) 0.0156(10) Uani 1 1 d . . . . .
N6 N 0.5115(3) 0.3380(3) 0.5080(3) 0.0301(12) Uani 1 1 d . . . . .
C24 C 0.7000(4) 0.6297(3) 0.5508(3) 0.0159(12) Uani 1 1 d . . . . .
C25 C 0.7627(4) 0.5578(3) 0.5583(3) 0.0177(12) Uani 1 1 d . . . . .
C26 C 0.7174(4) 0.4779(3) 0.5506(3) 0.0181(12) Uani 1 1 d . . . . .
C27 C 0.6131(4) 0.4760(3) 0.5341(3) 0.0175(12) Uani 1 1 d . . . . .
C28 C 0.5599(4) 0.5522(3) 0.5253(3) 0.0178(12) Uani 1 1 d . . . . .
C29 C 0.7449(4) 0.7118(3) 0.5615(3) 0.0170(12) Uani 1 1 d . . . . .
C30 C 0.8406(4) 0.7260(3) 0.5902(3) 0.0175(12) Uani 1 1 d . . . . .
C31 C 0.9047(4) 0.6529(3) 0.6174(3) 0.0214(12) Uani 1 1 d . . . . .
H31A H 0.8979 0.6431 0.6760 0.026 Uiso 1 1 calc R . . . .
H31B H 0.9754 0.6662 0.6087 0.026 Uiso 1 1 calc R . . . .
C32 C 0.8740(4) 0.5719(3) 0.5699(3) 0.0221(13) Uani 1 1 d . . . . .
H32A H 0.9027 0.5745 0.5159 0.027 Uiso 1 1 calc R . . . .
H32B H 0.9038 0.5221 0.5987 0.027 Uiso 1 1 calc R . . . .
C33 C 0.8521(4) 0.8166(3) 0.5977(3) 0.0193(12) Uani 1 1 d . . . . .
C34 C 0.7587(4) 0.8522(3) 0.5713(3) 0.0167(12) Uani 1 1 d . . . . .
C35 C 0.7411(4) 0.9398(3) 0.5708(3) 0.0187(12) Uani 1 1 d . . . . .
H35 H 0.6787 0.9628 0.5521 0.022 Uiso 1 1 calc R . . . .
C36 C 0.8187(4) 0.9913(3) 0.5987(3) 0.0216(13) Uani 1 1 d . . . . .
H36 H 0.8082 1.0509 0.6016 0.026 Uiso 1 1 calc R . . . .
C37 C 0.9125(4) 0.9584(3) 0.6228(3) 0.0225(13) Uani 1 1 d . . . . .
H37 H 0.9648 0.9963 0.6393 0.027 Uiso 1 1 calc R . . . .
C38 C 0.9307(4) 0.8715(3) 0.6231(3) 0.0201(13) Uani 1 1 d . . . . .
H38 H 0.9943 0.8497 0.6400 0.024 Uiso 1 1 calc R . . . .
C39 C 0.7742(4) 0.3963(3) 0.5603(3) 0.0187(12) Uani 1 1 d . . . . .
C40 C 0.7426(4) 0.3338(3) 0.6136(3) 0.0225(12) Uani 1 1 d . . . . .
H40 H 0.6841 0.3429 0.6425 0.027 Uiso 1 1 calc R . . . .
C41 C 0.7959(4) 0.2585(3) 0.6247(3) 0.0235(13) Uani 1 1 d . . . . .
H41 H 0.7732 0.2161 0.6602 0.028 Uiso 1 1 calc R . . . .
C42 C 0.8820(4) 0.2459(3) 0.5841(3) 0.0258(14) Uani 1 1 d . . . . .
H42 H 0.9198 0.1954 0.5931 0.031 Uiso 1 1 calc R . . . .
C43 C 0.9137(4) 0.3067(3) 0.5299(3) 0.0237(13) Uani 1 1 d . . . . .
H43 H 0.9722 0.2971 0.5012 0.028 Uiso 1 1 calc R . . . .
C44 C 0.8596(4) 0.3816(3) 0.5179(3) 0.0203(12) Uani 1 1 d . . . . .
H44 H 0.8812 0.4228 0.4807 0.024 Uiso 1 1 calc R . . . .
C45 C 0.5581(4) 0.3975(3) 0.5205(3) 0.0212(12) Uani 1 1 d . . . . .
C46 C 0.4068(4) 0.6257(3) 0.5035(3) 0.0248(13) Uani 1 1 d . . . . .
H46A H 0.4370 0.6651 0.4659 0.037 Uiso 1 1 calc GR . . . .
H46B H 0.4095 0.6504 0.5579 0.037 Uiso 1 1 calc GR . . . .
H46C H 0.3372 0.6154 0.4856 0.037 Uiso 1 1 calc GR . . . .
O4 O -0.1379(3) 0.3431(2) 0.8322(2) 0.0248(9) Uani 1 1 d . . . . .
N10 N 0.0795(3) 0.1058(2) 0.7504(3) 0.0236(11) Uani 1 1 d . . . . .
H10 H 0.0256 0.0990 0.7778 0.028 Uiso 1 1 calc R . . . .
N11 N -0.0118(3) 0.2632(3) 0.7812(2) 0.0210(10) Uani 1 1 d . . . . .
N12 N -0.1077(4) 0.5502(3) 0.8049(3) 0.0308(12) Uani 1 1 d . . . . .
C70 C 0.0697(4) 0.2629(3) 0.7371(3) 0.0209(12) Uani 1 1 d . . . . .
C71 C 0.1137(4) 0.3348(3) 0.7017(3) 0.0188(12) Uani 1 1 d . . . . .
C72 C 0.0723(4) 0.4143(3) 0.7208(3) 0.0184(12) Uani 1 1 d . . . . .
C73 C -0.0117(4) 0.4150(3) 0.7675(3) 0.0186(12) Uani 1 1 d . . . . .
C74 C -0.0525(4) 0.3381(4) 0.7937(3) 0.0208(12) Uani 1 1 d . . . . .
C75 C 0.1947(4) 0.3211(4) 0.6417(3) 0.0284(14) Uani 1 1 d . . . . .
H75A H 0.1624 0.3153 0.5868 0.034 Uiso 1 1 calc R . . . .
H75B H 0.2371 0.3725 0.6415 0.034 Uiso 1 1 calc R . . . .
C76 C 0.2616(4) 0.2444(3) 0.6578(3) 0.0260(14) Uani 1 1 d . . . . .
H76A H 0.2957 0.2296 0.6081 0.031 Uiso 1 1 calc R . . . .
H76B H 0.3132 0.2584 0.7007 0.031 Uiso 1 1 calc R . . . .
C77 C 0.2014(4) 0.1698(3) 0.6841(3) 0.0199(12) Uani 1 1 d . . . . .
C78 C 0.1147(4) 0.1813(3) 0.7226(3) 0.0209(13) Uani 1 1 d . . . . .
C79 C 0.2209(4) 0.0798(3) 0.6857(3) 0.0205(13) Uani 1 1 d . . . . .
C80 C 0.1425(4) 0.0425(3) 0.7284(3) 0.0212(12) Uani 1 1 d . . . . .
C81 C 0.1390(4) -0.0448(3) 0.7436(3) 0.0260(13) Uani 1 1 d . . . . .
H81 H 0.0879 -0.0689 0.7740 0.031 Uiso 1 1 calc R . . . .
C82 C 0.2129(4) -0.0946(4) 0.7128(3) 0.0257(13) Uani 1 1 d . . . . .
H82 H 0.2121 -0.1542 0.7218 0.031 Uiso 1 1 calc R . . . .
C83 C 0.2888(4) -0.0594(3) 0.6686(3) 0.0252(14) Uani 1 1 d . . . . .
H83 H 0.3377 -0.0957 0.6476 0.030 Uiso 1 1 calc R . . . .
C84 C 0.2945(4) 0.0271(3) 0.6545(3) 0.0241(13) Uani 1 1 d . . . . .
H84 H 0.3467 0.0502 0.6247 0.029 Uiso 1 1 calc R . . . .
C85 C 0.1146(4) 0.4958(3) 0.6928(3) 0.0191(12) Uani 1 1 d . . . . .
C86 C 0.1229(4) 0.5143(3) 0.6116(3) 0.0216(12) Uani 1 1 d . . . . .
H86 H 0.1034 0.4732 0.5718 0.026 Uiso 1 1 calc R . . . .
C87 C 0.1595(4) 0.5920(3) 0.5878(3) 0.0210(12) Uani 1 1 d . . . . .
H87 H 0.1652 0.6039 0.5319 0.025 Uiso 1 1 calc R . . . .
C88 C 0.1878(4) 0.6527(3) 0.6452(3) 0.0246(13) Uani 1 1 d . . . . .
H88 H 0.2115 0.7065 0.6286 0.030 Uiso 1 1 calc R . . . .
C89 C 0.1816(4) 0.6349(3) 0.7266(3) 0.0256(13) Uani 1 1 d . . . . .
H89 H 0.2028 0.6758 0.7660 0.031 Uiso 1 1 calc R . . . .
C90 C 0.1439(4) 0.5566(3) 0.7508(3) 0.0221(12) Uani 1 1 d . . . . .
H90 H 0.1383 0.5448 0.8067 0.027 Uiso 1 1 calc R . . . .
C91 C -0.0627(4) 0.4917(3) 0.7875(3) 0.0231(13) Uani 1 1 d . . . . .
C92 C -0.1820(4) 0.2634(3) 0.8565(3) 0.0290(14) Uani 1 1 d . . . . .
H92A H -0.1987 0.2289 0.8083 0.044 Uiso 1 1 calc GR . . . .
H92B H -0.2427 0.2749 0.8851 0.044 Uiso 1 1 calc GR . . . .
H92C H -0.1344 0.2325 0.8924 0.044 Uiso 1 1 calc GR . . . .


_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 C5 1.357(6) . ?
O1 C23 1.449(6) . ?
N1 H1 0.8800 . ?
N1 C6 1.382(6) . ?
N1 C11 1.364(6) . ?
N2 C1 1.352(6) . ?
N2 C5 1.313(6) . ?
N3 C22 1.146(6) . ?
C1 C2 1.412(7) . ?
C1 C6 1.439(7) . ?
C2 C3 1.396(7) . ?
C2 C9 1.508(7) . ?
C3 C4 1.406(7) . ?
C3 C16 1.498(7) . ?
C4 C5 1.403(7) . ?
C4 C22 1.430(7) . ?
C6 C7 1.366(7) . ?
C7 C8 1.491(7) . ?
C7 C10 1.435(7) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.519(7) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.422(7) . ?
C10 C15 1.409(7) . ?
C11 C12 1.397(7) . ?
C12 H12 0.9500 . ?
C12 C13 1.383(7) . ?
C13 H13 0.9500 . ?
C13 C14 1.398(7) . ?
C14 H14 0.9500 . ?
C14 C15 1.378(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.390(7) . ?
C16 C21 1.402(7) . ?
C17 H17 0.9500 . ?
C17 C18 1.393(7) . ?
C18 H18 0.9500 . ?
C18 C19 1.393(7) . ?
C19 H19 0.9500 . ?
C19 C20 1.375(7) . ?
C20 H20 0.9500 . ?
C20 C21 1.374(7) . ?
C21 H21 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
O3 C51 1.342(6) . ?
O3 C69 1.454(6) . ?
N7 H7 0.8800 . ?
N7 C52 1.379(6) . ?
N7 C57 1.373(7) . ?
N8 C47 1.351(6) . ?
N8 C51 1.318(6) . ?
N9 C68 1.147(6) . ?
C47 C48 1.396(7) . ?
C47 C52 1.448(7) . ?
C48 C49 1.396(7) . ?
C48 C55 1.521(7) . ?
C49 C50 1.415(7) . ?
C49 C62 1.491(7) . ?
C50 C51 1.404(7) . ?
C50 C68 1.426(8) . ?
C52 C53 1.362(7) . ?
C53 C54 1.496(7) . ?
C53 C56 1.433(7) . ?
C54 H54A 0.9900 . ?
C54 H54B 0.9900 . ?
C54 C55 1.532(7) . ?
C55 H55A 0.9900 . ?
C55 H55B 0.9900 . ?
C56 C57 1.409(7) . ?
C56 C61 1.397(7) . ?
C57 C58 1.411(7) . ?
C58 H58 0.9500 . ?
C58 C59 1.375(8) . ?
C59 H59 0.9500 . ?
C59 C60 1.404(8) . ?
C60 H60 0.9500 . ?
C60 C61 1.385(7) . ?
C61 H61 0.9500 . ?
C62 C63 1.383(7) . ?
C62 C67 1.396(7) . ?
C63 H63 0.9500 . ?
C63 C64 1.395(7) . ?
C64 H64 0.9500 . ?
C64 C65 1.383(7) . ?
C65 H65 0.9500 . ?
C65 C66 1.379(7) . ?
C66 H66 0.9500 . ?
C66 C67 1.383(7) . ?
C67 H67 0.9500 . ?
C69 H69A 0.9800 . ?
C69 H69B 0.9800 . ?
C69 H69C 0.9800 . ?
O2 C28 1.357(6) . ?
O2 C46 1.448(6) . ?
N4 H4 0.8800 . ?
N4 C29 1.380(6) . ?
N4 C34 1.378(6) . ?
N5 C24 1.346(6) . ?
N5 C28 1.313(6) . ?
N6 C45 1.140(6) . ?
C24 C25 1.412(7) . ?
C24 C29 1.434(7) . ?
C25 C26 1.400(7) . ?
C25 C32 1.513(7) . ?
C26 C27 1.414(7) . ?
C26 C39 1.499(7) . ?
C27 C28 1.400(7) . ?
C27 C45 1.451(7) . ?
C29 C30 1.366(7) . ?
C30 C31 1.494(7) . ?
C30 C33 1.440(7) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.543(7) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.423(7) . ?
C33 C38 1.411(7) . ?
C34 C35 1.399(7) . ?
C35 H35 0.9500 . ?
C35 C36 1.381(7) . ?
C36 H36 0.9500 . ?
C36 C37 1.401(7) . ?
C37 H37 0.9500 . ?
C37 C38 1.390(7) . ?
C38 H38 0.9500 . ?
C39 C40 1.402(7) . ?
C39 C44 1.393(7) . ?
C40 H40 0.9500 . ?
C40 C41 1.392(7) . ?
C41 H41 0.9500 . ?
C41 C42 1.381(7) . ?
C42 H42 0.9500 . ?
C42 C43 1.392(7) . ?
C43 H43 0.9500 . ?
C43 C44 1.394(7) . ?
C44 H44 0.9500 . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
O4 C74 1.341(6) . ?
O4 C92 1.453(6) . ?
N10 H10 0.8800 . ?
N10 C78 1.368(6) . ?
N10 C80 1.367(6) . ?
N11 C70 1.345(6) . ?
N11 C74 1.320(6) . ?
N12 C91 1.147(6) . ?
C70 C71 1.418(7) . ?
C70 C78 1.444(7) . ?
C71 C72 1.412(7) . ?
C71 C75 1.525(7) . ?
C72 C73 1.399(7) . ?
C72 C85 1.485(7) . ?
C73 C74 1.407(7) . ?
C73 C91 1.435(7) . ?
C75 H75A 0.9900 . ?
C75 H75B 0.9900 . ?
C75 C76 1.521(7) . ?
C76 H76A 0.9900 . ?
C76 H76B 0.9900 . ?
C76 C77 1.503(7) . ?
C77 C78 1.368(7) . ?
C77 C79 1.440(7) . ?
C79 C80 1.424(7) . ?
C79 C84 1.409(7) . ?
C80 C81 1.399(7) . ?
C81 H81 0.9500 . ?
C81 C82 1.383(7) . ?
C82 H82 0.9500 . ?
C82 C83 1.398(7) . ?
C83 H83 0.9500 . ?
C83 C84 1.383(7) . ?
C84 H84 0.9500 . ?
C85 C86 1.385(7) . ?
C85 C90 1.398(7) . ?
C86 H86 0.9500 . ?
C86 C87 1.383(7) . ?
C87 H87 0.9500 . ?
C87 C88 1.386(7) . ?
C88 H88 0.9500 . ?
C88 C89 1.381(7) . ?
C89 H89 0.9500 . ?
C89 C90 1.398(7) . ?
C90 H90 0.9500 . ?
C92 H92A 0.9800 . ?
C92 H92B 0.9800 . ?
C92 H92C 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
C5 O1 C23 116.7(4) . . ?
C6 N1 H1 125.8 . . ?
C11 N1 H1 125.8 . . ?
C11 N1 C6 108.4(4) . . ?
C5 N2 C1 116.5(4) . . ?
N2 C1 C2 125.3(5) . . ?
N2 C1 C6 117.4(5) . . ?
C2 C1 C6 117.3(5) . . ?
C1 C2 C9 118.9(5) . . ?
C3 C2 C1 116.7(5) . . ?
C3 C2 C9 123.9(5) . . ?
C2 C3 C4 118.5(5) . . ?
C2 C3 C16 122.9(5) . . ?
C4 C3 C16 118.6(4) . . ?
C3 C4 C22 122.6(5) . . ?
C5 C4 C3 119.1(5) . . ?
C5 C4 C22 118.2(5) . . ?
O1 C5 C4 116.5(5) . . ?
N2 C5 O1 119.6(5) . . ?
N2 C5 C4 123.9(5) . . ?
N1 C6 C1 124.1(5) . . ?
C7 C6 N1 110.6(5) . . ?
C7 C6 C1 125.3(5) . . ?
C6 C7 C8 120.5(5) . . ?
C6 C7 C10 106.2(5) . . ?
C10 C7 C8 133.2(5) . . ?
C7 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
C7 C8 C9 111.6(4) . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C2 C9 C8 117.5(5) . . ?
C2 C9 H9A 107.9 . . ?
C2 C9 H9B 107.9 . . ?
C8 C9 H9A 107.9 . . ?
C8 C9 H9B 107.9 . . ?
H9A C9 H9B 107.2 . . ?
C11 C10 C7 106.7(5) . . ?
C15 C10 C7 134.7(5) . . ?
C15 C10 C11 118.6(5) . . ?
N1 C11 C10 108.1(5) . . ?
N1 C11 C12 129.5(5) . . ?
C12 C11 C10 122.4(5) . . ?
C11 C12 H12 121.6 . . ?
C13 C12 C11 116.9(5) . . ?
C13 C12 H12 121.5 . . ?
C12 C13 H13 119.0 . . ?
C12 C13 C14 122.0(5) . . ?
C14 C13 H13 119.0 . . ?
C13 C14 H14 119.4 . . ?
C15 C14 C13 121.2(5) . . ?
C15 C14 H14 119.4 . . ?
C10 C15 H15 120.5 . . ?
C14 C15 C10 119.0(5) . . ?
C14 C15 H15 120.5 . . ?
C17 C16 C3 119.3(5) . . ?
C17 C16 C21 118.7(5) . . ?
C21 C16 C3 122.0(5) . . ?
C16 C17 H17 119.6 . . ?
C16 C17 C18 120.8(5) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 120.3 . . ?
C17 C18 C19 119.3(5) . . ?
C19 C18 H18 120.3 . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.9(5) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 H20 119.5 . . ?
C21 C20 C19 121.0(5) . . ?
C21 C20 H20 119.5 . . ?
C16 C21 H21 119.9 . . ?
C20 C21 C16 120.1(5) . . ?
C20 C21 H21 119.9 . . ?
N3 C22 C4 177.9(6) . . ?
O1 C23 H23A 109.5 . . ?
O1 C23 H23B 109.5 . . ?
O1 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C51 O3 C69 116.4(4) . . ?
C52 N7 H7 126.3 . . ?
C57 N7 H7 126.3 . . ?
C57 N7 C52 107.4(4) . . ?
C51 N8 C47 116.5(5) . . ?
N8 C47 C48 125.9(5) . . ?
N8 C47 C52 116.8(5) . . ?
C48 C47 C52 117.3(5) . . ?
C47 C48 C55 119.0(5) . . ?
C49 C48 C47 116.7(5) . . ?
C49 C48 C55 124.1(5) . . ?
C48 C49 C50 118.2(5) . . ?
C48 C49 C62 123.0(5) . . ?
C50 C49 C62 118.7(5) . . ?
C49 C50 C68 122.7(5) . . ?
C51 C50 C49 119.1(5) . . ?
C51 C50 C68 118.1(5) . . ?
O3 C51 C50 117.3(5) . . ?
N8 C51 O3 119.3(5) . . ?
N8 C51 C50 123.4(5) . . ?
N7 C52 C47 124.0(5) . . ?
C53 C52 N7 110.7(5) . . ?
C53 C52 C47 125.1(5) . . ?
C52 C53 C54 119.7(5) . . ?
C52 C53 C56 106.7(5) . . ?
C56 C53 C54 133.1(5) . . ?
C53 C54 H54A 109.5 . . ?
C53 C54 H54B 109.5 . . ?
C53 C54 C55 110.8(4) . . ?
H54A C54 H54B 108.1 . . ?
C55 C54 H54A 109.5 . . ?
C55 C54 H54B 109.5 . . ?
C48 C55 C54 114.9(4) . . ?
C48 C55 H55A 108.5 . . ?
C48 C55 H55B 108.5 . . ?
C54 C55 H55A 108.5 . . ?
C54 C55 H55B 108.5 . . ?
H55A C55 H55B 107.5 . . ?
C57 C56 C53 106.1(5) . . ?
C61 C56 C53 134.2(5) . . ?
C61 C56 C57 119.7(5) . . ?
N7 C57 C56 109.0(4) . . ?
N7 C57 C58 128.3(5) . . ?
C56 C57 C58 122.8(5) . . ?
C57 C58 H58 122.2 . . ?
C59 C58 C57 115.7(6) . . ?
C59 C58 H58 122.2 . . ?
C58 C59 H59 118.7 . . ?
C58 C59 C60 122.6(5) . . ?
C60 C59 H59 118.7 . . ?
C59 C60 H60 119.4 . . ?
C61 C60 C59 121.3(5) . . ?
C61 C60 H60 119.4 . . ?
C56 C61 H61 121.0 . . ?
C60 C61 C56 118.0(5) . . ?
C60 C61 H61 121.0 . . ?
C63 C62 C49 119.2(5) . . ?
C63 C62 C67 119.0(5) . . ?
C67 C62 C49 121.8(5) . . ?
C62 C63 H63 119.8 . . ?
C62 C63 C64 120.3(5) . . ?
C64 C63 H63 119.8 . . ?
C63 C64 H64 120.1 . . ?
C65 C64 C63 119.9(5) . . ?
C65 C64 H64 120.1 . . ?
C64 C65 H65 119.9 . . ?
C66 C65 C64 120.2(5) . . ?
C66 C65 H65 119.9 . . ?
C65 C66 H66 120.1 . . ?
C65 C66 C67 119.9(5) . . ?
C67 C66 H66 120.1 . . ?
C62 C67 H67 119.6 . . ?
C66 C67 C62 120.7(5) . . ?
C66 C67 H67 119.6 . . ?
N9 C68 C50 176.6(6) . . ?
O3 C69 H69A 109.5 . . ?
O3 C69 H69B 109.5 . . ?
O3 C69 H69C 109.5 . . ?
H69A C69 H69B 109.5 . . ?
H69A C69 H69C 109.5 . . ?
H69B C69 H69C 109.5 . . ?
C28 O2 C46 115.5(4) . . ?
C29 N4 H4 126.2 . . ?
C34 N4 H4 126.2 . . ?
C34 N4 C29 107.5(4) . . ?
C28 N5 C24 116.7(4) . . ?
N5 C24 C25 125.2(4) . . ?
N5 C24 C29 117.0(5) . . ?
C25 C24 C29 117.8(5) . . ?
C24 C25 C32 118.3(5) . . ?
C26 C25 C24 117.2(5) . . ?
C26 C25 C32 124.4(5) . . ?
C25 C26 C27 117.3(5) . . ?
C25 C26 C39 123.0(5) . . ?
C27 C26 C39 119.7(4) . . ?
C26 C27 C45 122.7(5) . . ?
C28 C27 C26 119.7(5) . . ?
C28 C27 C45 117.5(5) . . ?
O2 C28 C27 117.0(5) . . ?
N5 C28 O2 119.3(5) . . ?
N5 C28 C27 123.7(5) . . ?
N4 C29 C24 123.8(5) . . ?
C30 C29 N4 111.0(4) . . ?
C30 C29 C24 125.0(5) . . ?
C29 C30 C31 119.7(5) . . ?
C29 C30 C33 106.7(4) . . ?
C33 C30 C31 132.9(5) . . ?
C30 C31 H31A 109.6 . . ?
C30 C31 H31B 109.6 . . ?
C30 C31 C32 110.5(4) . . ?
H31A C31 H31B 108.1 . . ?
C32 C31 H31A 109.6 . . ?
C32 C31 H31B 109.6 . . ?
C25 C32 C31 115.0(4) . . ?
C25 C32 H32A 108.5 . . ?
C25 C32 H32B 108.5 . . ?
C31 C32 H32A 108.5 . . ?
C31 C32 H32B 108.5 . . ?
H32A C32 H32B 107.5 . . ?
C34 C33 C30 105.9(4) . . ?
C38 C33 C30 135.1(5) . . ?
C38 C33 C34 119.0(5) . . ?
N4 C34 C33 108.8(4) . . ?
N4 C34 C35 128.8(5) . . ?
C35 C34 C33 122.4(5) . . ?
C34 C35 H35 121.5 . . ?
C36 C35 C34 116.9(5) . . ?
C36 C35 H35 121.5 . . ?
C35 C36 H36 119.0 . . ?
C35 C36 C37 122.0(5) . . ?
C37 C36 H36 119.0 . . ?
C36 C37 H37 119.3 . . ?
C38 C37 C36 121.3(5) . . ?
C38 C37 H37 119.3 . . ?
C33 C38 H38 120.9 . . ?
C37 C38 C33 118.3(5) . . ?
C37 C38 H38 120.9 . . ?
C40 C39 C26 120.0(5) . . ?
C44 C39 C26 121.1(5) . . ?
C44 C39 C40 118.8(5) . . ?
C39 C40 H40 119.6 . . ?
C41 C40 C39 120.7(5) . . ?
C41 C40 H40 119.6 . . ?
C40 C41 H41 120.1 . . ?
C42 C41 C40 119.8(5) . . ?
C42 C41 H41 120.1 . . ?
C41 C42 H42 119.9 . . ?
C41 C42 C43 120.3(5) . . ?
C43 C42 H42 119.9 . . ?
C42 C43 H43 120.0 . . ?
C42 C43 C44 120.0(5) . . ?
C44 C43 H43 120.0 . . ?
C39 C44 C43 120.4(5) . . ?
C39 C44 H44 119.8 . . ?
C43 C44 H44 119.8 . . ?
N6 C45 C27 176.8(6) . . ?
O2 C46 H46A 109.5 . . ?
O2 C46 H46B 109.5 . . ?
O2 C46 H46C 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C74 O4 C92 116.8(4) . . ?
C78 N10 H10 125.8 . . ?
C80 N10 H10 125.8 . . ?
C80 N10 C78 108.4(5) . . ?
C74 N11 C70 116.3(5) . . ?
N11 C70 C71 126.0(5) . . ?
N11 C70 C78 116.9(5) . . ?
C71 C70 C78 117.1(5) . . ?
C70 C71 C75 118.8(5) . . ?
C72 C71 C70 116.1(5) . . ?
C72 C71 C75 124.9(5) . . ?
C71 C72 C85 122.4(5) . . ?
C73 C72 C71 117.9(5) . . ?
C73 C72 C85 119.8(5) . . ?
C72 C73 C74 120.1(5) . . ?
C72 C73 C91 122.8(5) . . ?
C74 C73 C91 117.0(5) . . ?
O4 C74 C73 116.9(5) . . ?
N11 C74 O4 119.8(5) . . ?
N11 C74 C73 123.3(5) . . ?
C71 C75 H75A 108.4 . . ?
C71 C75 H75B 108.4 . . ?
H75A C75 H75B 107.4 . . ?
C76 C75 C71 115.6(5) . . ?
C76 C75 H75A 108.4 . . ?
C76 C75 H75B 108.4 . . ?
C75 C76 H76A 109.5 . . ?
C75 C76 H76B 109.5 . . ?
H76A C76 H76B 108.1 . . ?
C77 C76 C75 110.5(5) . . ?
C77 C76 H76A 109.5 . . ?
C77 C76 H76B 109.5 . . ?
C78 C77 C76 120.9(5) . . ?
C78 C77 C79 106.3(5) . . ?
C79 C77 C76 132.4(5) . . ?
N10 C78 C70 124.3(5) . . ?
C77 C78 N10 110.9(5) . . ?
C77 C78 C70 124.7(5) . . ?
C80 C79 C77 106.0(5) . . ?
C84 C79 C77 134.7(5) . . ?
C84 C79 C80 119.2(5) . . ?
N10 C80 C79 108.3(4) . . ?
N10 C80 C81 129.9(5) . . ?
C81 C80 C79 121.8(5) . . ?
C80 C81 H81 121.3 . . ?
C82 C81 C80 117.4(5) . . ?
C82 C81 H81 121.3 . . ?
C81 C82 H82 119.2 . . ?
C81 C82 C83 121.5(5) . . ?
C83 C82 H82 119.2 . . ?
C82 C83 H83 119.1 . . ?
C84 C83 C82 121.8(5) . . ?
C84 C83 H83 119.1 . . ?
C79 C84 H84 120.9 . . ?
C83 C84 C79 118.2(5) . . ?
C83 C84 H84 120.9 . . ?
C86 C85 C72 122.3(4) . . ?
C86 C85 C90 119.1(5) . . ?
C90 C85 C72 118.5(4) . . ?
C85 C86 H86 119.7 . . ?
C87 C86 C85 120.6(5) . . ?
C87 C86 H86 119.7 . . ?
C86 C87 H87 119.8 . . ?
C86 C87 C88 120.3(5) . . ?
C88 C87 H87 119.8 . . ?
C87 C88 H88 120.0 . . ?
C89 C88 C87 119.9(5) . . ?
C89 C88 H88 120.0 . . ?
C88 C89 H89 120.1 . . ?
C88 C89 C90 119.9(5) . . ?
C90 C89 H89 120.1 . . ?
C85 C90 C89 120.1(5) . . ?
C85 C90 H90 119.9 . . ?
C89 C90 H90 119.9 . . ?
N12 C91 C73 176.2(6) . . ?
O4 C92 H92A 109.5 . . ?
O4 C92 H92B 109.5 . . ?
O4 C92 H92C 109.5 . . ?
H92A C92 H92B 109.5 . . ?
H92A C92 H92C 109.5 . . ?
H92B C92 H92C 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
N1 H1 N12 0.88 2.14 3.000(6) 165.6 2_546
N7 H7 N9 0.88 2.07 2.934(7) 165.5 2_557
N4 H4 N6 0.88 2.12 2.982(6) 166.1 2_656
N10 H10 N3 0.88 2.10 2.960(6) 165.0 2_546

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
N1 C6 C7 C8 -176.8(5) . . . . ?
N1 C6 C7 C10 1.2(6) . . . . ?
N1 C11 C12 C13 178.5(5) . . . . ?
N2 C1 C2 C3 -0.2(7) . . . . ?
N2 C1 C2 C9 -172.2(5) . . . . ?
N2 C1 C6 N1 5.4(7) . . . . ?
N2 C1 C6 C7 -175.5(5) . . . . ?
C1 N2 C5 O1 -179.2(4) . . . . ?
C1 N2 C5 C4 1.1(7) . . . . ?
C1 C2 C3 C4 0.4(7) . . . . ?
C1 C2 C3 C16 -177.9(4) . . . . ?
C1 C2 C9 C8 -27.3(7) . . . . ?
C1 C6 C7 C8 4.1(8) . . . . ?
C1 C6 C7 C10 -177.9(5) . . . . ?
C2 C1 C6 N1 -172.7(5) . . . . ?
C2 C1 C6 C7 6.4(8) . . . . ?
C2 C3 C4 C5 0.1(7) . . . . ?
C2 C3 C4 C22 176.8(5) . . . . ?
C2 C3 C16 C17 119.1(6) . . . . ?
C2 C3 C16 C21 -62.1(7) . . . . ?
C3 C2 C9 C8 161.3(5) . . . . ?
C3 C4 C5 O1 179.4(4) . . . . ?
C3 C4 C5 N2 -0.9(7) . . . . ?
C3 C16 C17 C18 179.3(5) . . . . ?
C3 C16 C21 C20 -178.1(5) . . . . ?
C4 C3 C16 C17 -59.2(7) . . . . ?
C4 C3 C16 C21 119.6(6) . . . . ?
C5 N2 C1 C2 -0.5(7) . . . . ?
C5 N2 C1 C6 -178.5(5) . . . . ?
C6 N1 C11 C10 0.5(6) . . . . ?
C6 N1 C11 C12 -177.1(5) . . . . ?
C6 C1 C2 C3 177.7(5) . . . . ?
C6 C1 C2 C9 5.7(7) . . . . ?
C6 C7 C8 C9 -24.3(7) . . . . ?
C6 C7 C10 C11 -0.9(6) . . . . ?
C6 C7 C10 C15 177.8(6) . . . . ?
C7 C8 C9 C2 35.2(7) . . . . ?
C7 C10 C11 N1 0.2(6) . . . . ?
C7 C10 C11 C12 178.1(5) . . . . ?
C7 C10 C15 C14 -178.5(6) . . . . ?
C8 C7 C10 C11 176.7(6) . . . . ?
C8 C7 C10 C15 -4.5(10) . . . . ?
C9 C2 C3 C4 172.0(5) . . . . ?
C9 C2 C3 C16 -6.3(8) . . . . ?
C10 C7 C8 C9 158.3(6) . . . . ?
C10 C11 C12 C13 1.1(8) . . . . ?
C11 N1 C6 C1 178.0(5) . . . . ?
C11 N1 C6 C7 -1.1(6) . . . . ?
C11 C10 C15 C14 0.1(8) . . . . ?
C11 C12 C13 C14 -0.6(8) . . . . ?
C12 C13 C14 C15 -0.1(8) . . . . ?
C13 C14 C15 C10 0.4(8) . . . . ?
C15 C10 C11 N1 -178.8(4) . . . . ?
C15 C10 C11 C12 -0.9(8) . . . . ?
C16 C3 C4 C5 178.5(5) . . . . ?
C16 C3 C4 C22 -4.9(7) . . . . ?
C16 C17 C18 C19 -1.2(8) . . . . ?
C17 C16 C21 C20 0.7(8) . . . . ?
C17 C18 C19 C20 0.9(8) . . . . ?
C18 C19 C20 C21 0.3(8) . . . . ?
C19 C20 C21 C16 -1.1(8) . . . . ?
C21 C16 C17 C18 0.4(8) . . . . ?
C22 C4 C5 O1 2.6(7) . . . . ?
C22 C4 C5 N2 -177.7(5) . . . . ?
C23 O1 C5 N2 8.2(7) . . . . ?
C23 O1 C5 C4 -172.2(4) . . . . ?
N7 C52 C53 C54 171.7(4) . . . . ?
N7 C52 C53 C56 -1.1(6) . . . . ?
N7 C57 C58 C59 178.4(5) . . . . ?
N8 C47 C48 C49 -3.3(7) . . . . ?
N8 C47 C48 C55 173.6(5) . . . . ?
N8 C47 C52 N7 -4.0(7) . . . . ?
N8 C47 C52 C53 171.3(5) . . . . ?
C47 N8 C51 O3 -178.5(4) . . . . ?
C47 N8 C51 C50 1.2(7) . . . . ?
C47 C48 C49 C50 2.6(7) . . . . ?
C47 C48 C49 C62 -175.0(5) . . . . ?
C47 C48 C55 C54 32.4(7) . . . . ?
C47 C52 C53 C54 -4.1(8) . . . . ?
C47 C52 C53 C56 -176.9(5) . . . . ?
C48 C47 C52 N7 176.3(5) . . . . ?
C48 C47 C52 C53 -8.4(7) . . . . ?
C48 C49 C50 C51 -0.5(7) . . . . ?
C48 C49 C50 C68 177.2(5) . . . . ?
C48 C49 C62 C63 122.1(6) . . . . ?
C48 C49 C62 C67 -58.6(7) . . . . ?
C49 C48 C55 C54 -151.0(5) . . . . ?
C49 C50 C51 O3 178.1(4) . . . . ?
C49 C50 C51 N8 -1.6(7) . . . . ?
C49 C62 C63 C64 -178.8(5) . . . . ?
C49 C62 C67 C66 179.4(5) . . . . ?
C50 C49 C62 C63 -55.5(7) . . . . ?
C50 C49 C62 C67 123.7(5) . . . . ?
C51 N8 C47 C48 1.3(7) . . . . ?
C51 N8 C47 C52 -178.4(4) . . . . ?
C52 N7 C57 C56 -1.0(5) . . . . ?
C52 N7 C57 C58 178.9(5) . . . . ?
C52 C47 C48 C49 176.4(5) . . . . ?
C52 C47 C48 C55 -6.7(7) . . . . ?
C52 C53 C54 C55 28.9(7) . . . . ?
C52 C53 C56 C57 0.4(6) . . . . ?
C52 C53 C56 C61 178.7(6) . . . . ?
C53 C54 C55 C48 -41.8(6) . . . . ?
C53 C56 C57 N7 0.3(6) . . . . ?
C53 C56 C57 C58 -179.5(5) . . . . ?
C53 C56 C61 C60 -178.7(5) . . . . ?
C54 C53 C56 C57 -170.9(5) . . . . ?
C54 C53 C56 C61 7.4(10) . . . . ?
C55 C48 C49 C50 -174.1(5) . . . . ?
C55 C48 C49 C62 8.3(8) . . . . ?
C56 C53 C54 C55 -160.6(5) . . . . ?
C56 C57 C58 C59 -1.8(8) . . . . ?
C57 N7 C52 C47 177.1(5) . . . . ?
C57 N7 C52 C53 1.3(6) . . . . ?
C57 C56 C61 C60 -0.6(8) . . . . ?
C57 C58 C59 C60 0.6(8) . . . . ?
C58 C59 C60 C61 0.6(9) . . . . ?
C59 C60 C61 C56 -0.6(8) . . . . ?
C61 C56 C57 N7 -178.3(4) . . . . ?
C61 C56 C57 C58 1.9(8) . . . . ?
C62 C49 C50 C51 177.3(4) . . . . ?
C62 C49 C50 C68 -5.1(8) . . . . ?
C62 C63 C64 C65 -0.9(8) . . . . ?
C63 C62 C67 C66 -1.3(8) . . . . ?
C63 C64 C65 C66 -0.8(8) . . . . ?
C64 C65 C66 C67 1.4(8) . . . . ?
C65 C66 C67 C62 -0.3(8) . . . . ?
C67 C62 C63 C64 1.9(8) . . . . ?
C68 C50 C51 O3 0.4(7) . . . . ?
C68 C50 C51 N8 -179.3(5) . . . . ?
C69 O3 C51 N8 -3.7(6) . . . . ?
C69 O3 C51 C50 176.5(4) . . . . ?
N4 C29 C30 C31 172.1(4) . . . . ?
N4 C29 C30 C33 0.3(6) . . . . ?
N4 C34 C35 C36 177.7(5) . . . . ?
N5 C24 C25 C26 -2.9(7) . . . . ?
N5 C24 C25 C32 174.2(4) . . . . ?
N5 C24 C29 N4 -4.8(7) . . . . ?
N5 C24 C29 C30 170.2(5) . . . . ?
C24 N5 C28 O2 -177.5(4) . . . . ?
C24 N5 C28 C27 0.7(7) . . . . ?
C24 C25 C26 C27 1.5(7) . . . . ?
C24 C25 C26 C39 -177.7(5) . . . . ?
C24 C25 C32 C31 32.2(7) . . . . ?
C24 C29 C30 C31 -3.4(8) . . . . ?
C24 C29 C30 C33 -175.2(5) . . . . ?
C25 C24 C29 N4 174.7(5) . . . . ?
C25 C24 C29 C30 -10.4(7) . . . . ?
C25 C26 C27 C28 0.7(7) . . . . ?
C25 C26 C27 C45 176.6(5) . . . . ?
C25 C26 C39 C40 127.9(5) . . . . ?
C25 C26 C39 C44 -51.0(7) . . . . ?
C26 C25 C32 C31 -150.9(5) . . . . ?
C26 C27 C28 O2 176.3(4) . . . . ?
C26 C27 C28 N5 -1.9(8) . . . . ?
C26 C39 C40 C41 -178.4(5) . . . . ?
C26 C39 C44 C43 177.5(4) . . . . ?
C27 C26 C39 C40 -51.3(7) . . . . ?
C27 C26 C39 C44 129.8(5) . . . . ?
C28 N5 C24 C25 1.8(7) . . . . ?
C28 N5 C24 C29 -178.8(4) . . . . ?
C29 N4 C34 C33 -0.2(5) . . . . ?
C29 N4 C34 C35 -179.1(5) . . . . ?
C29 C24 C25 C26 177.7(4) . . . . ?
C29 C24 C25 C32 -5.2(7) . . . . ?
C29 C30 C31 C32 29.5(7) . . . . ?
C29 C30 C33 C34 -0.4(6) . . . . ?
C29 C30 C33 C38 -179.8(6) . . . . ?
C30 C31 C32 C25 -42.8(6) . . . . ?
C30 C33 C34 N4 0.4(5) . . . . ?
C30 C33 C34 C35 179.4(5) . . . . ?
C30 C33 C38 C37 -179.3(5) . . . . ?
C31 C30 C33 C34 -170.7(5) . . . . ?
C31 C30 C33 C38 9.9(10) . . . . ?
C32 C25 C26 C27 -175.4(5) . . . . ?
C32 C25 C26 C39 5.4(8) . . . . ?
C33 C30 C31 C32 -161.2(5) . . . . ?
C33 C34 C35 C36 -1.1(7) . . . . ?
C34 N4 C29 C24 175.5(5) . . . . ?
C34 N4 C29 C30 -0.1(6) . . . . ?
C34 C33 C38 C37 1.3(7) . . . . ?
C34 C35 C36 C37 3.0(8) . . . . ?
C35 C36 C37 C38 -2.9(8) . . . . ?
C36 C37 C38 C33 0.5(8) . . . . ?
C38 C33 C34 N4 179.9(4) . . . . ?
C38 C33 C34 C35 -1.1(7) . . . . ?
C39 C26 C27 C28 179.9(4) . . . . ?
C39 C26 C27 C45 -4.2(7) . . . . ?
C39 C40 C41 C42 1.3(8) . . . . ?
C40 C39 C44 C43 -1.4(7) . . . . ?
C40 C41 C42 C43 -2.2(8) . . . . ?
C41 C42 C43 C44 1.4(8) . . . . ?
C42 C43 C44 C39 0.5(7) . . . . ?
C44 C39 C40 C41 0.5(7) . . . . ?
C45 C27 C28 O2 0.2(7) . . . . ?
C45 C27 C28 N5 -178.1(5) . . . . ?
C46 O2 C28 N5 -7.0(6) . . . . ?
C46 O2 C28 C27 174.6(4) . . . . ?
N10 C80 C81 C82 179.2(5) . . . . ?
N11 C70 C71 C72 5.5(7) . . . . ?
N11 C70 C71 C75 -169.5(5) . . . . ?
N11 C70 C78 N10 0.3(7) . . . . ?
N11 C70 C78 C77 -175.1(5) . . . . ?
C70 N11 C74 O4 175.3(4) . . . . ?
C70 N11 C74 C73 -3.7(7) . . . . ?
C70 C71 C72 C73 -4.3(7) . . . . ?
C70 C71 C72 C85 175.9(4) . . . . ?
C70 C71 C75 C76 -33.3(7) . . . . ?
C71 C70 C78 N10 -178.1(5) . . . . ?
C71 C70 C78 C77 6.5(8) . . . . ?
C71 C72 C73 C74 -0.2(7) . . . . ?
C71 C72 C73 C91 -177.2(4) . . . . ?
C71 C72 C85 C86 59.0(7) . . . . ?
C71 C72 C85 C90 -123.0(5) . . . . ?
C71 C75 C76 C77 40.7(6) . . . . ?
C72 C71 C75 C76 152.1(5) . . . . ?
C72 C73 C74 O4 -174.4(5) . . . . ?
C72 C73 C74 N11 4.6(7) . . . . ?
C72 C85 C86 C87 177.7(5) . . . . ?
C72 C85 C90 C89 -178.3(5) . . . . ?
C73 C72 C85 C86 -120.8(6) . . . . ?
C73 C72 C85 C90 57.2(7) . . . . ?
C74 N11 C70 C71 -1.5(7) . . . . ?
C74 N11 C70 C78 -179.7(4) . . . . ?
C75 C71 C72 C73 170.4(5) . . . . ?
C75 C71 C72 C85 -9.4(7) . . . . ?
C75 C76 C77 C78 -27.5(7) . . . . ?
C75 C76 C77 C79 160.8(5) . . . . ?
C76 C77 C78 N10 -171.9(4) . . . . ?
C76 C77 C78 C70 4.1(8) . . . . ?
C76 C77 C79 C80 171.3(5) . . . . ?
C76 C77 C79 C84 -10.2(10) . . . . ?
C77 C79 C80 N10 0.5(6) . . . . ?
C77 C79 C80 C81 -178.1(5) . . . . ?
C77 C79 C84 C83 -179.9(5) . . . . ?
C78 N10 C80 C79 0.6(6) . . . . ?
C78 N10 C80 C81 179.0(5) . . . . ?
C78 C70 C71 C72 -176.2(5) . . . . ?
C78 C70 C71 C75 8.7(7) . . . . ?
C78 C77 C79 C80 -1.3(6) . . . . ?
C78 C77 C79 C84 177.2(6) . . . . ?
C79 C77 C78 N10 1.8(6) . . . . ?
C79 C77 C78 C70 177.7(5) . . . . ?
C79 C80 C81 C82 -2.5(8) . . . . ?
C80 N10 C78 C70 -177.5(5) . . . . ?
C80 N10 C78 C77 -1.5(6) . . . . ?
C80 C79 C84 C83 -1.5(7) . . . . ?
C80 C81 C82 C83 0.5(8) . . . . ?
C81 C82 C83 C84 0.9(8) . . . . ?
C82 C83 C84 C79 -0.4(8) . . . . ?
C84 C79 C80 N10 -178.3(4) . . . . ?
C84 C79 C80 C81 3.1(8) . . . . ?
C85 C72 C73 C74 179.6(4) . . . . ?
C85 C72 C73 C91 2.6(8) . . . . ?
C85 C86 C87 C88 -0.3(8) . . . . ?
C86 C85 C90 C89 -0.3(8) . . . . ?
C86 C87 C88 C89 1.4(8) . . . . ?
C87 C88 C89 C90 -1.9(8) . . . . ?
C88 C89 C90 C85 1.3(8) . . . . ?
C90 C85 C86 C87 -0.2(8) . . . . ?
C91 C73 C74 O4 2.7(7) . . . . ?
C91 C73 C74 N11 -178.2(5) . . . . ?
C92 O4 C74 N11 -1.4(7) . . . . ?
C92 O4 C74 C73 177.7(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
