# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_step-64
_database_code_depnum_ccdc_archive 'CCDC 1556702'
_audit_update_record             
;
2017-06-20 deposited with the CCDC.
2017-11-01 downloaded from the CCDC.
;
_audit_creation_date             2017-06-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H29 N3'
_chemical_formula_sum            'C36 H29 N3'
_chemical_formula_weight         503.62
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C36 H29 N3'
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'

_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                   16.4746(7)
_cell_length_b                   9.1306(3)
_cell_length_c                   19.2167(8)
_cell_angle_alpha                90
_cell_angle_beta                 113.764(5)
_cell_angle_gamma                90
_cell_volume                     2645.56(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5625
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.8060
_cell_measurement_theta_min      3.3230
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96172
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            17160
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_min         2.623
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -27.00   -1.00   1.0000    7.3000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  -57.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -44.00   41.00   1.0000    7.3000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   57.0000    0.0000 85

#__ type_ start__ end____ width___ exp.time_
  3 omega  -96.00  -71.00   1.0000    7.3000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241 -172.0000  -25.0000 25

#__ type_ start__ end____ width___ exp.time_
  4 omega  -46.00    4.00   1.0000    7.3000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   38.0000  -30.0000 50

#__ type_ start__ end____ width___ exp.time_
  5 omega   -7.00   93.00   1.0000    7.3000
omega____ theta____ kappa____ phi______ frames
    -       23.3616   77.0000 -150.0000 100

#__ type_ start__ end____ width___ exp.time_
  6 omega  -95.00  -45.00   1.0000    7.3000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  -38.0000   90.0000 50
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0031503000
_diffrn_orient_matrix_UB_12      0.0082484000
_diffrn_orient_matrix_UB_13      -0.0377142000
_diffrn_orient_matrix_UB_21      0.0459273000
_diffrn_orient_matrix_UB_22      -0.0153808000
_diffrn_orient_matrix_UB_23      0.0126782000
_diffrn_orient_matrix_UB_31      -0.0096600000
_diffrn_orient_matrix_UB_32      -0.0756956000
_diffrn_orient_matrix_UB_33      -0.0066712000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5088
_reflns_number_total             6077
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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         0.311
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         6077
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0406
_refine_ls_restrained_S_all      1.021
_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)+(0.0437P)²+1.0708P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.1024
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6A(H6A), C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C6(H6B,H6C), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C1'(H1'), C12(H12), C18(H18), C4'(H4'), C17(H17), C2'(H2'),
 C16(H16), C19(H19), C25(H25), C3'(H3'), C21(H21), C7'(H7'), C9'(H9'), C8'(H8'),
  C6'(H6'), C22(H22), C24(H24), C23(H23)
2.d X=CH2 refined with riding coordinates:
 C13(H13A,H13B)
;
_atom_sites_solution_hydrogens   geom
_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
N3 N 0.21677(7) -0.07616(11) 0.19346(5) 0.0172(2) Uani 1 1 d . . . . .
N5' N 0.01055(7) 0.26801(11) 0.02305(6) 0.0185(2) Uani 1 1 d . . . . .
N10' N 0.11067(6) 0.21853(11) 0.18328(6) 0.0170(2) Uani 1 1 d . . . . .
C15 C 0.32746(8) 0.27182(13) 0.08770(7) 0.0183(2) Uani 1 1 d . . . . .
H15 H 0.3441 0.1820 0.0721 0.022 Uiso 1 1 calc R . . . .
C1' C 0.22950(8) -0.09725(13) 0.03628(7) 0.0188(2) Uani 1 1 d . . . . .
H1' H 0.2783 -0.1504 0.0716 0.023 Uiso 1 1 calc R . . . .
C6B C 0.33200(7) 0.08074(13) 0.26596(6) 0.0159(2) Uani 1 1 d . . . . .
C2 C 0.20374(7) 0.04636(13) 0.14243(6) 0.0149(2) Uani 1 1 d . . . . .
C11A C 0.18424(8) 0.00284(13) 0.06111(6) 0.0156(2) Uani 1 1 d . . . . .
C10A C 0.12731(7) 0.15229(13) 0.13049(6) 0.0151(2) Uani 1 1 d . . . . .
C14 C 0.30081(7) 0.27234(13) 0.14818(6) 0.0153(2) Uani 1 1 d . . . . .
C6A C 0.26362(8) -0.02499(13) 0.27122(6) 0.0174(2) Uani 1 1 d . . . . .
H6A H 0.2213 0.0301 0.2870 0.021 Uiso 1 1 calc R . . . .
C12 C 0.46113(8) 0.08748(14) 0.21987(7) 0.0196(3) Uani 1 1 d . . . . .
H12 H 0.4780 0.1824 0.2411 0.023 Uiso 1 1 calc R . . . .
C1A C 0.29378(7) 0.12858(13) 0.18251(6) 0.0148(2) Uani 1 1 d . . . . .
C4A' C 0.11281(8) 0.08130(13) 0.00903(7) 0.0163(2) Uani 1 1 d . . . . .
C18 C 0.27975(8) 0.53404(14) 0.13259(7) 0.0206(3) Uani 1 1 d . . . . .
H18 H 0.2637 0.6243 0.1482 0.025 Uiso 1 1 calc R . . . .
C20 C 0.37795(8) 0.17128(13) 0.33573(6) 0.0173(2) Uani 1 1 d . . . . .
C1 C 0.37533(8) 0.02787(13) 0.21418(6) 0.0164(2) Uani 1 1 d . . . . .
H1 H 0.3642 -0.0771 0.1982 0.020 Uiso 1 1 calc R . . . .
C4' C 0.08649(8) 0.06194(14) -0.06879(7) 0.0211(3) Uani 1 1 d . . . . .
H4' H 0.0387 0.1169 -0.1042 0.025 Uiso 1 1 calc R . . . .
C17 C 0.30643(8) 0.53103(14) 0.07280(7) 0.0216(3) Uani 1 1 d . . . . .
H17 H 0.3085 0.6192 0.0473 0.026 Uiso 1 1 calc R . . . .
C4B' C 0.07675(7) 0.17562(13) 0.05085(6) 0.0159(2) Uani 1 1 d . . . . .
C5A' C -0.00735(8) 0.34218(13) 0.07738(7) 0.0178(2) Uani 1 1 d . . . . .
C2' C 0.20220(9) -0.11864(14) -0.04157(7) 0.0223(3) Uani 1 1 d . . . . .
H2' H 0.2321 -0.1882 -0.0596 0.027 Uiso 1 1 calc R . . . .
C16 C 0.33004(8) 0.39974(14) 0.05015(7) 0.0212(3) Uani 1 1 d . . . . .
H16 H 0.3480 0.3975 0.0090 0.025 Uiso 1 1 calc R . . . .
C19 C 0.27650(8) 0.40518(13) 0.16964(7) 0.0179(2) Uani 1 1 d . . . . .
H19 H 0.2574 0.4077 0.2102 0.021 Uiso 1 1 calc R . . . .
C25 C 0.33280(8) 0.28048(14) 0.35621(7) 0.0208(3) Uani 1 1 d . . . . .
H25 H 0.2737 0.3044 0.3230 0.025 Uiso 1 1 calc R . . . .
C4 C 0.14989(8) -0.17860(14) 0.19396(7) 0.0203(3) Uani 1 1 d . . . . .
H4A H 0.1319 -0.2465 0.1501 0.024 Uiso 1 1 calc R . . . .
H4B H 0.0968 -0.1273 0.1937 0.024 Uiso 1 1 calc R . . . .
C9A' C 0.04108(8) 0.31663(13) 0.15643(7) 0.0173(2) Uani 1 1 d . . . . .
C6 C 0.28608(9) -0.17020(14) 0.31339(7) 0.0227(3) Uani 1 1 d . . . . .
H6B H 0.2974 -0.1579 0.3677 0.027 Uiso 1 1 calc R . . . .
H6C H 0.3383 -0.2167 0.3094 0.027 Uiso 1 1 calc R . . . .
C3' C 0.13142(9) -0.03908(14) -0.09341(7) 0.0237(3) Uani 1 1 d . . . . .
H3' H 0.1139 -0.0546 -0.1464 0.028 Uiso 1 1 calc R . . . .
C21 C 0.46366(8) 0.13509(15) 0.38632(7) 0.0222(3) Uani 1 1 d . . . . .
H21 H 0.4951 0.0598 0.3736 0.027 Uiso 1 1 calc R . . . .
C7' C -0.09461(9) 0.52498(15) 0.10655(8) 0.0251(3) Uani 1 1 d . . . . .
H7' H -0.1404 0.5964 0.0902 0.030 Uiso 1 1 calc R . . . .
C9' C 0.01934(8) 0.39627(14) 0.20909(7) 0.0220(3) Uani 1 1 d . . . . .
H9' H 0.0507 0.3785 0.2620 0.026 Uiso 1 1 calc R . . . .
C8' C -0.04659(9) 0.49934(15) 0.18495(8) 0.0251(3) Uani 1 1 d . . . . .
H8' H -0.0600 0.5537 0.2211 0.030 Uiso 1 1 calc R . . . .
C5 C 0.20034(9) -0.26010(15) 0.27036(7) 0.0244(3) Uani 1 1 d . . . . .
H5A H 0.1636 -0.2648 0.3003 0.029 Uiso 1 1 calc R . . . .
H5B H 0.2152 -0.3612 0.2609 0.029 Uiso 1 1 calc R . . . .
C6' C -0.07572(8) 0.44781(14) 0.05391(7) 0.0225(3) Uani 1 1 d . . . . .
H6' H -0.1088 0.4654 0.0012 0.027 Uiso 1 1 calc R . . . .
C22 C 0.50341(9) 0.20839(16) 0.45528(7) 0.0278(3) Uani 1 1 d . . . . .
H22 H 0.5617 0.1825 0.4895 0.033 Uiso 1 1 calc R . . . .
C24 C 0.37334(9) 0.35468(15) 0.42464(7) 0.0251(3) Uani 1 1 d . . . . .
H24 H 0.3424 0.4306 0.4374 0.030 Uiso 1 1 calc R . . . .
C13 C 0.51563(9) 0.01578(16) 0.19703(8) 0.0264(3) Uani 1 1 d . . . . .
H13A H 0.5004 -0.0793 0.1756 0.032 Uiso 1 1 calc R . . . .
H13B H 0.5701 0.0593 0.2020 0.032 Uiso 1 1 calc R . . . .
C23 C 0.45880(9) 0.31844(16) 0.47435(7) 0.0270(3) Uani 1 1 d . . . . .
H23 H 0.4865 0.3691 0.5212 0.032 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N3 C2 1.4455(15) . ?
N3 C6A 1.4550(15) . ?
N3 C4 1.4482(15) . ?
N5' C4B' 1.3103(15) . ?
N5' C5A' 1.3725(16) . ?
N10' C10A 1.3017(15) . ?
N10' C9A' 1.3806(15) . ?
C15 C14 1.3982(17) . ?
C15 C16 1.3826(17) . ?
C1' C11A 1.3803(17) . ?
C1' C2' 1.3915(17) . ?
C6B C6A 1.5176(16) . ?
C6B C1A 1.5315(15) . ?
C6B C20 1.4954(16) . ?
C6B C1 1.5183(16) . ?
C2 C11A 1.5162(16) . ?
C2 C10A 1.5299(16) . ?
C2 C1A 1.5609(15) . ?
C11A C4A' 1.3967(16) . ?
C10A C4B' 1.4331(16) . ?
C14 C1A 1.4944(16) . ?
C14 C19 1.3909(17) . ?
C6A C6 1.5199(17) . ?
C12 C1 1.4771(16) . ?
C12 C13 1.3211(18) . ?
C1A C1 1.5369(15) . ?
C4A' C4' 1.3903(16) . ?
C4A' C4B' 1.4579(17) . ?
C18 C17 1.3861(18) . ?
C18 C19 1.3873(17) . ?
C20 C25 1.3921(17) . ?
C20 C21 1.3936(17) . ?
C4' C3' 1.3802(18) . ?
C17 C16 1.3835(18) . ?
C5A' C9A' 1.4219(17) . ?
C5A' C6' 1.4118(17) . ?
C2' C3' 1.3940(18) . ?
C25 C24 1.3880(18) . ?
C4 C5 1.5545(17) . ?
C9A' C9' 1.4046(17) . ?
C6 C5 1.5529(18) . ?
C21 C22 1.3904(18) . ?
C7' C8' 1.4107(19) . ?
C7' C6' 1.3675(19) . ?
C9' C8' 1.3691(18) . ?
C22 C23 1.379(2) . ?
C24 C23 1.3857(19) . ?

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
C2 N3 C6A 108.69(9) . . ?
C2 N3 C4 126.80(9) . . ?
C4 N3 C6A 106.90(9) . . ?
C4B' N5' C5A' 113.96(10) . . ?
C10A N10' C9A' 114.47(10) . . ?
C16 C15 C14 121.13(11) . . ?
C11A C1' C2' 118.62(11) . . ?
C6A C6B C1A 104.37(9) . . ?
C6A C6B C1 113.52(10) . . ?
C20 C6B C6A 114.40(10) . . ?
C20 C6B C1A 128.84(10) . . ?
C20 C6B C1 124.17(10) . . ?
C1 C6B C1A 60.52(7) . . ?
N3 C2 C11A 114.10(9) . . ?
N3 C2 C10A 118.64(10) . . ?
N3 C2 C1A 100.70(9) . . ?
C11A C2 C10A 101.03(9) . . ?
C11A C2 C1A 113.52(9) . . ?
C10A C2 C1A 109.33(9) . . ?
C1' C11A C2 127.61(11) . . ?
C1' C11A C4A' 120.56(11) . . ?
C4A' C11A C2 111.80(10) . . ?
N10' C10A C2 126.58(10) . . ?
N10' C10A C4B' 123.28(11) . . ?
C4B' C10A C2 110.08(10) . . ?
C15 C14 C1A 118.04(10) . . ?
C19 C14 C15 118.28(11) . . ?
C19 C14 C1A 123.52(10) . . ?
N3 C6A C6B 103.69(9) . . ?
N3 C6A C6 100.48(10) . . ?
C6B C6A C6 124.24(10) . . ?
C13 C12 C1 123.44(12) . . ?
C6B C1A C2 106.70(9) . . ?
C6B C1A C1 59.31(7) . . ?
C14 C1A C6B 129.83(10) . . ?
C14 C1A C2 115.59(9) . . ?
C14 C1A C1 119.31(10) . . ?
C1 C1A C2 114.38(9) . . ?
C11A C4A' C4B' 108.72(10) . . ?
C4' C4A' C11A 120.86(11) . . ?
C4' C4A' C4B' 130.42(11) . . ?
C17 C18 C19 119.95(12) . . ?
C25 C20 C6B 120.95(11) . . ?
C25 C20 C21 118.64(11) . . ?
C21 C20 C6B 119.93(11) . . ?
C6B C1 C1A 60.17(7) . . ?
C12 C1 C6B 121.53(10) . . ?
C12 C1 C1A 117.81(10) . . ?
C3' C4' C4A' 118.42(11) . . ?
C16 C17 C18 120.08(12) . . ?
N5' C4B' C10A 124.15(11) . . ?
N5' C4B' C4A' 127.78(11) . . ?
C10A C4B' C4A' 108.07(10) . . ?
N5' C5A' C9A' 122.12(11) . . ?
N5' C5A' C6' 118.84(11) . . ?
C6' C5A' C9A' 119.04(11) . . ?
C1' C2' C3' 120.67(12) . . ?
C15 C16 C17 119.74(12) . . ?
C18 C19 C14 120.81(11) . . ?
C24 C25 C20 120.63(12) . . ?
N3 C4 C5 101.35(9) . . ?
N10' C9A' C5A' 121.98(11) . . ?
N10' C9A' C9' 118.76(11) . . ?
C9' C9A' C5A' 119.24(11) . . ?
C6A C6 C5 101.74(10) . . ?
C4' C3' C2' 120.86(11) . . ?
C22 C21 C20 120.42(12) . . ?
C6' C7' C8' 120.51(12) . . ?
C8' C9' C9A' 120.64(12) . . ?
C9' C8' C7' 120.18(12) . . ?
C6 C5 C4 105.98(10) . . ?
C7' C6' C5A' 120.38(12) . . ?
C23 C22 C21 120.48(12) . . ?
C23 C24 C25 120.26(13) . . ?
C22 C23 C24 119.54(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_step-63
_database_code_depnum_ccdc_archive 'CCDC 1556703'
_audit_update_record             
;
2017-06-17 deposited with the CCDC.
2017-11-01 downloaded from the CCDC.
;
_audit_creation_date             2017-06-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C39 H31 N3 O, (C2 H5 O H)0.675'
_chemical_formula_sum            'C40.35 H35.05 N3 O1.67'
_chemical_formula_weight         588.76
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C39 N3 h29'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0006(3)
_cell_length_b                   13.4106(7)
_cell_length_c                   13.9272(4)
_cell_angle_alpha                73.859(4)
_cell_angle_beta                 78.251(3)
_cell_angle_gamma                71.617(4)
_cell_volume                     1519.94(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4875
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.5910
_cell_measurement_theta_min      3.3210
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.616
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             623
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10039
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.986
_diffrn_reflns_theta_min         3.331
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -45.00   35.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.5037   38.0000  120.0000 80

#__ type_ start__ end____ width___ exp.time_
  2 omega -116.00  -44.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.5037  178.0000   60.0000 72

#__ type_ start__ end____ width___ exp.time_
  3 omega -114.00  -12.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.5037  -57.0000  -30.0000 102

#__ type_ start__ end____ width___ exp.time_
  4 omega  -38.00   74.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       40.5037  -77.0000 -120.0000 112

#__ type_ start__ end____ width___ exp.time_
  5 omega  104.00  130.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       40.5037  178.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega   45.00   76.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -180.0000 31

#__ type_ start__ end____ width___ exp.time_
  7 omega   50.00  106.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  150.0000 56

#__ type_ start__ end____ width___ exp.time_
  8 omega   29.00  104.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -120.0000 75

#__ type_ start__ end____ width___ exp.time_
  9 omega  105.00  175.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -150.0000 70

#__ type_ start__ end____ width___ exp.time_
 10 omega   87.00  132.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  -60.0000 45

#__ type_ start__ end____ width___ exp.time_
 11 omega   86.00  112.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 12 omega   43.00   87.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   60.0000 44

#__ type_ start__ end____ width___ exp.time_
 13 omega   37.00  109.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   60.0000 72

#__ type_ start__ end____ width___ exp.time_
 14 omega   38.00   94.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  120.0000 56

#__ type_ start__ end____ width___ exp.time_
 15 omega   39.00   74.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   30.0000 35

#__ type_ start__ end____ width___ exp.time_
 16 omega   45.00  114.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  120.0000 69

#__ type_ start__ end____ width___ exp.time_
 17 omega   44.00  137.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000 -120.0000 93

#__ type_ start__ end____ width___ exp.time_
 18 omega   31.00  162.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000 -150.0000 131
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1291673000
_diffrn_orient_matrix_UB_12      0.0235851000
_diffrn_orient_matrix_UB_13      0.0407168000
_diffrn_orient_matrix_UB_21      -0.0912499000
_diffrn_orient_matrix_UB_22      0.1205968000
_diffrn_orient_matrix_UB_23      -0.0183470000
_diffrn_orient_matrix_UB_31      -0.0897564000
_diffrn_orient_matrix_UB_32      -0.0193246000
_diffrn_orient_matrix_UB_33      0.1071645000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4772
_reflns_number_total             5735
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     70.33
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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         0.526
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.051
_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     432
_refine_ls_number_reflns         5735
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0478
_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)+(0.0716P)²+0.4434P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1249
_refine_ls_wR_factor_ref         0.1337
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 H3-N3
 0.85 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C2S) = Uanis(C3S)
Uanis(O1) = Uanis(O1A)
4. Others
 Sof(H1SC)=Sof(H1SD)=Sof(C3S)=Sof(H3SA)=Sof(H3SB)=Sof(H3SC)=0.34*FVAR(2)
 Sof(H1SA)=Sof(H1SB)=Sof(C2S)=Sof(H2SA)=Sof(H2SB)=Sof(H2SC)=0.66*FVAR(2)
 Sof(O1S)=Sof(H1S)=Sof(C1S)=FVAR(1)
 Sof(H11C)=Sof(H11D)=Sof(O1)=Sof(H1)=1-FVAR(2)
 Sof(O1A)=Sof(H1A)=Sof(H11A)=Sof(H11B)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C4(H4), C6(H6)
5.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C11(H11A,H11B), C11(H11C,H11D), C1S(H1SA,H1SB), C1S(H1SC,H1SD)
5.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C18(H18), C6'(H6'), C15(H15), C9'(H9'), C30(H30), C24(H24),
 C7'(H7'), C26(H26), C20(H20), C8'(H8'), C16(H16), C1'(H1'), C17(H17), C4'(H4'),
  C3'(H3'), C21(H21), C27(H27), C29(H29), C2'(H2'), C22(H22), C28(H28), C23(H23)
5.d Idealised Me refined as rotating group:
 C2S(H2SA,H2SB,H2SC), C3S(H3SA,H3SB,H3SC)
5.e Idealised tetrahedral OH refined as rotating group:
 O1A(H1A), O1S(H1S), O1(H1)
;
_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
N5' N 0.20299(16) 0.54667(11) 0.49439(9) 0.0192(3) Uani 1 1 d . . . . .
N10' N 0.28046(16) 0.32388(11) 0.60334(9) 0.0192(3) Uani 1 1 d . . . . .
N3 N -0.06740(16) 0.30935(11) 0.70027(10) 0.0203(3) Uani 1 1 d D . . . .
O1A O -0.0665(2) 0.11626(15) 0.57931(12) 0.0427(5) Uani 0.895(3) 1 d . . P A 3
H1A H -0.1144 0.1060 0.5387 0.064 Uiso 0.895(3) 1 calc GR . P A 3
C5A' C 0.33720(18) 0.47198(13) 0.46527(11) 0.0186(3) Uani 1 1 d . . . . .
C4B' C 0.11690(18) 0.50822(13) 0.57625(11) 0.0178(3) Uani 1 1 d . . . . .
C13 C 0.20814(18) 0.35094(13) 0.84581(10) 0.0179(3) Uani 1 1 d . . . . .
C1 C 0.09175(18) 0.31192(13) 0.81334(11) 0.0181(3) Uani 1 1 d . . . . .
C9 C -0.08044(19) 0.49242(13) 0.71132(11) 0.0198(3) Uani 1 1 d . . . . .
C25 C 0.22770(19) 0.09622(13) 0.85288(11) 0.0205(3) Uani 1 1 d . . . . .
C9A' C 0.37757(19) 0.36242(13) 0.52028(11) 0.0187(3) Uani 1 1 d . . . . .
C2 C 0.02278(18) 0.37739(13) 0.71491(11) 0.0187(3) Uani 1 1 d . . . . .
C4A' C -0.02732(19) 0.56676(13) 0.62929(11) 0.0199(3) Uani 1 1 d . . . . .
C19 C -0.02554(19) 0.24102(13) 1.00355(11) 0.0196(3) Uani 1 1 d . . . . .
C5 C 0.09741(18) 0.19528(13) 0.82155(11) 0.0188(3) Uani 1 1 d . . . . .
C14 C 0.37128(19) 0.30720(13) 0.82760(11) 0.0194(3) Uani 1 1 d . . . . .
H14 H 0.4124 0.2522 0.7909 0.023 Uiso 1 1 calc R . . . .
C10A C 0.15383(18) 0.39673(13) 0.62859(11) 0.0180(3) Uani 1 1 d . . . . .
C18 C 0.1512(2) 0.43458(14) 0.89688(12) 0.0225(3) Uani 1 1 d . . . . .
H18 H 0.0408 0.4669 0.9079 0.027 Uiso 1 1 calc R . . . .
C6' C 0.44042(19) 0.50572(14) 0.37962(11) 0.0217(3) Uani 1 1 d . . . . .
H6' H 0.4133 0.5781 0.3413 0.026 Uiso 1 1 calc R . . . .
C15 C 0.47389(19) 0.34352(14) 0.86276(11) 0.0220(3) Uani 1 1 d . . . . .
H15 H 0.5846 0.3127 0.8505 0.026 Uiso 1 1 calc R . . . .
C4 C 0.02494(19) 0.19669(13) 0.72970(11) 0.0206(3) Uani 1 1 d . . . . .
H4 H 0.1112 0.1789 0.6741 0.025 Uiso 1 1 calc R . . . .
C6 C -0.02372(18) 0.25881(13) 0.89251(11) 0.0195(3) Uani 1 1 d . . . . .
H6 H -0.1324 0.2830 0.8725 0.023 Uiso 1 1 calc R . . . .
C9' C 0.5214(2) 0.29136(14) 0.49045(12) 0.0223(3) Uani 1 1 d . . . . .
H9' H 0.5499 0.2184 0.5273 0.027 Uiso 1 1 calc R . . . .
C30 C 0.2149(2) 0.02243(14) 0.94508(12) 0.0237(3) Uani 1 1 d . . . . .
H30 H 0.1220 0.0360 0.9917 0.028 Uiso 1 1 calc R . . . .
C24 C -0.1722(2) 0.25097(14) 1.06294(12) 0.0232(3) Uani 1 1 d . . . . .
H24 H -0.2646 0.2683 1.0318 0.028 Uiso 1 1 calc R . . . .
C7' C 0.5790(2) 0.43471(15) 0.35171(11) 0.0240(3) Uani 1 1 d . . . . .
H7' H 0.6474 0.4580 0.2940 0.029 Uiso 1 1 calc R . . . .
C26 C 0.3637(2) 0.07157(14) 0.78433(12) 0.0235(3) Uani 1 1 d . . . . .
H26 H 0.3740 0.1202 0.7207 0.028 Uiso 1 1 calc R . . . .
C20 C 0.1078(2) 0.21566(14) 1.05143(12) 0.0233(3) Uani 1 1 d . . . . .
H20 H 0.2090 0.2079 1.0127 0.028 Uiso 1 1 calc R . . . .
C8' C 0.6210(2) 0.32717(15) 0.40811(12) 0.0242(3) Uani 1 1 d . . . . .
H8' H 0.7188 0.2790 0.3892 0.029 Uiso 1 1 calc R . . . .
C16 C 0.4155(2) 0.42468(15) 0.91575(12) 0.0256(4) Uani 1 1 d . . . . .
H16 H 0.4858 0.4483 0.9409 0.031 Uiso 1 1 calc R . . . .
C1' C -0.2171(2) 0.52786(15) 0.77403(12) 0.0247(3) Uani 1 1 d . . . . .
H1' H -0.2543 0.4783 0.8296 0.030 Uiso 1 1 calc R . . . .
C17 C 0.2540(2) 0.47091(15) 0.93165(12) 0.0266(4) Uani 1 1 d . . . . .
H17 H 0.2136 0.5276 0.9664 0.032 Uiso 1 1 calc R . . . .
C4' C -0.1085(2) 0.67585(14) 0.60874(12) 0.0236(3) Uani 1 1 d . . . . .
H4' H -0.0715 0.7256 0.5532 0.028 Uiso 1 1 calc R . . . .
C3' C -0.2457(2) 0.70990(15) 0.67213(13) 0.0272(4) Uani 1 1 d . . . . .
H3' H -0.3040 0.7839 0.6592 0.033 Uiso 1 1 calc R . . . .
C21 C 0.0943(2) 0.20163(15) 1.15532(12) 0.0267(4) Uani 1 1 d . . . . .
H21 H 0.1861 0.1851 1.1868 0.032 Uiso 1 1 calc R . . . .
C27 C 0.4834(2) -0.02269(15) 0.80796(14) 0.0279(4) Uani 1 1 d . . . . .
H27 H 0.5743 -0.0385 0.7603 0.033 Uiso 1 1 calc R . . . .
C29 C 0.3365(2) -0.07052(14) 0.96933(13) 0.0284(4) Uani 1 1 d . . . . .
H29 H 0.3276 -0.1185 1.0335 0.034 Uiso 1 1 calc R . . . .
C12 C -0.0783(2) 0.11971(15) 0.75291(12) 0.0261(4) Uani 1 1 d . . . . .
H12A H -0.0101 0.0446 0.7675 0.031 Uiso 1 1 calc R . . . .
H12B H -0.1528 0.1307 0.8145 0.031 Uiso 1 1 calc R . . . .
C2' C -0.2988(2) 0.63688(15) 0.75439(13) 0.0276(4) Uani 1 1 d . . . . .
H2' H -0.3918 0.6619 0.7974 0.033 Uiso 1 1 calc R . . . .
O1S O 0.1854(3) -0.05930(19) 0.55911(18) 0.0481(8) Uani 0.675(4) 1 d . . P B .
H1S H 0.1105 -0.0027 0.5581 0.072 Uiso 0.675(4) 1 calc GR . P . .
C22 C -0.0518(2) 0.21155(16) 1.21334(12) 0.0322(4) Uani 1 1 d . . . . .
H22 H -0.0603 0.2017 1.2843 0.039 Uiso 1 1 calc R . . . .
C28 C 0.4708(2) -0.09440(15) 0.90142(14) 0.0293(4) Uani 1 1 d . . . . .
H28 H 0.5531 -0.1587 0.9182 0.035 Uiso 1 1 calc R . . . .
C23 C -0.1852(2) 0.23591(16) 1.16725(13) 0.0309(4) Uani 1 1 d . . . . .
H23 H -0.2858 0.2424 1.2066 0.037 Uiso 1 1 calc R . . . .
C11 C -0.1721(3) 0.13363(19) 0.66872(15) 0.0413(5) Uani 1 1 d . . . . .
H11A H -0.2360 0.0813 0.6890 0.050 Uiso 0.895(3) 1 calc R . P A 3
H11B H -0.2448 0.2074 0.6555 0.050 Uiso 0.895(3) 1 calc R . P A 3
H11C H -0.1591 0.0610 0.6587 0.050 Uiso 0.105(3) 1 calc R . P A 4
H11D H -0.2850 0.1629 0.6924 0.050 Uiso 0.105(3) 1 calc R . P A 4
C1S C 0.3053(5) -0.0510(3) 0.5989(2) 0.0510(10) Uani 0.675(4) 1 d . . P . .
H1SA H 0.3737 -0.1249 0.6214 0.061 Uiso 0.446(3) 1 calc R . P B -1
H1SB H 0.2593 -0.0221 0.6598 0.061 Uiso 0.446(3) 1 calc R . P B -1
H1SC H 0.4038 -0.1097 0.5922 0.061 Uiso 0.2296(14) 1 calc R . P B 2
H1SD H 0.2764 -0.0429 0.6693 0.061 Uiso 0.2296(14) 1 calc R . P B 2
C2S C 0.4132(8) 0.0197(5) 0.5311(4) 0.0567(14) Uani 0.446(3) 1 d . . P B -1
H2SA H 0.4515 -0.0022 0.4670 0.085 Uiso 0.446(3) 1 calc GR . P B -1
H2SB H 0.5033 0.0098 0.5656 0.085 Uiso 0.446(3) 1 calc GR . P B -1
H2SC H 0.3525 0.0959 0.5183 0.085 Uiso 0.446(3) 1 calc GR . P B -1
H3 H -0.091(3) 0.3269(17) 0.6401(12) 0.028(5) Uiso 1 1 d D . . . .
C3S C 0.3073(17) 0.0563(10) 0.5206(9) 0.0567(14) Uani 0.2296(14) 1 d . . P B 2
H3SA H 0.3344 0.0430 0.4527 0.085 Uiso 0.2296(14) 1 calc GR . P B 2
H3SB H 0.3860 0.0859 0.5336 0.085 Uiso 0.2296(14) 1 calc GR . P B 2
H3SC H 0.2028 0.1081 0.5261 0.085 Uiso 0.2296(14) 1 calc GR . P B 2
O1 O -0.1372(19) 0.1991(13) 0.5746(10) 0.0427(5) Uani 0.105(3) 1 d . . P A 4
H1 H -0.2004 0.2033 0.5359 0.064 Uiso 0.105(3) 1 calc GR . P A 4


_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
N5' C5A' 1.375(2) . ?
N5' C4B' 1.316(2) . ?
N10' C9A' 1.382(2) . ?
N10' C10A 1.305(2) . ?
N3 C2 1.474(2) . ?
N3 C4 1.464(2) . ?
N3 H3 0.857(15) . ?
O1A H1A 0.8400 . ?
O1A C11 1.431(3) . ?
C5A' C9A' 1.424(2) . ?
C5A' C6' 1.416(2) . ?
C4B' C4A' 1.462(2) . ?
C4B' C10A 1.434(2) . ?
C13 C1 1.499(2) . ?
C13 C14 1.397(2) . ?
C13 C18 1.400(2) . ?
C1 C2 1.539(2) . ?
C1 C5 1.521(2) . ?
C1 C6 1.5384(19) . ?
C9 C2 1.522(2) . ?
C9 C4A' 1.405(2) . ?
C9 C1' 1.388(2) . ?
C25 C5 1.495(2) . ?
C25 C30 1.395(2) . ?
C25 C26 1.401(2) . ?
C9A' C9' 1.407(2) . ?
C2 C10A 1.532(2) . ?
C4A' C4' 1.391(2) . ?
C19 C6 1.495(2) . ?
C19 C24 1.396(2) . ?
C19 C20 1.394(2) . ?
C5 C4 1.543(2) . ?
C5 C6 1.528(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.389(2) . ?
C18 H18 0.9500 . ?
C18 C17 1.388(2) . ?
C6' H6' 0.9500 . ?
C6' C7' 1.369(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.391(3) . ?
C4 H4 1.0000 . ?
C4 C12 1.527(2) . ?
C6 H6 1.0000 . ?
C9' H9' 0.9500 . ?
C9' C8' 1.377(2) . ?
C30 H30 0.9500 . ?
C30 C29 1.387(3) . ?
C24 H24 0.9500 . ?
C24 C23 1.395(2) . ?
C7' H7' 0.9500 . ?
C7' C8' 1.410(2) . ?
C26 H26 0.9500 . ?
C26 C27 1.386(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.391(2) . ?
C8' H8' 0.9500 . ?
C16 H16 0.9500 . ?
C16 C17 1.387(3) . ?
C1' H1' 0.9500 . ?
C1' C2' 1.391(3) . ?
C17 H17 0.9500 . ?
C4' H4' 0.9500 . ?
C4' C3' 1.392(2) . ?
C3' H3' 0.9500 . ?
C3' C2' 1.396(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.384(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.395(2) . ?
C29 H29 0.9500 . ?
C29 C28 1.384(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C11 1.518(2) . ?
C2' H2' 0.9500 . ?
O1S H1S 0.8400 . ?
O1S C1S 1.356(5) . ?
C22 H22 0.9500 . ?
C22 C23 1.382(3) . ?
C28 H28 0.9500 . ?
C23 H23 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 H11C 0.9900 . ?
C11 H11D 0.9900 . ?
C11 O1 1.398(15) . ?
C1S H1SA 0.9900 . ?
C1S H1SB 0.9900 . ?
C1S H1SC 0.9900 . ?
C1S H1SD 0.9900 . ?
C1S C2S 1.563(6) . ?
C1S C3S 1.549(12) . ?
C2S H2SA 0.9800 . ?
C2S H2SB 0.9800 . ?
C2S H2SC 0.9800 . ?
C3S H3SA 0.9800 . ?
C3S H3SB 0.9800 . ?
C3S H3SC 0.9800 . ?
O1 H1 0.8400 . ?

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
C4B' N5' C5A' 114.44(13) . . ?
C10A N10' C9A' 114.47(13) . . ?
C2 N3 H3 112.1(14) . . ?
C4 N3 C2 107.46(12) . . ?
C4 N3 H3 113.2(15) . . ?
C11 O1A H1A 109.5 . . ?
N5' C5A' C9A' 121.95(14) . . ?
N5' C5A' C6' 118.97(14) . . ?
C6' C5A' C9A' 119.06(15) . . ?
N5' C4B' C4A' 128.13(15) . . ?
N5' C4B' C10A 123.43(15) . . ?
C10A C4B' C4A' 108.45(13) . . ?
C14 C13 C1 122.84(14) . . ?
C14 C13 C18 118.49(14) . . ?
C18 C13 C1 118.68(14) . . ?
C13 C1 C2 117.40(13) . . ?
C13 C1 C5 127.01(13) . . ?
C13 C1 C6 120.18(12) . . ?
C5 C1 C2 106.02(12) . . ?
C5 C1 C6 59.91(10) . . ?
C6 C1 C2 113.62(12) . . ?
C4A' C9 C2 111.94(14) . . ?
C1' C9 C2 128.32(15) . . ?
C1' C9 C4A' 119.66(16) . . ?
C30 C25 C5 122.62(15) . . ?
C30 C25 C26 118.17(16) . . ?
C26 C25 C5 119.03(14) . . ?
N10' C9A' C5A' 121.91(15) . . ?
N10' C9A' C9' 118.77(14) . . ?
C9' C9A' C5A' 119.32(14) . . ?
N3 C2 C1 102.38(12) . . ?
N3 C2 C9 110.86(13) . . ?
N3 C2 C10A 113.91(13) . . ?
C9 C2 C1 118.17(13) . . ?
C9 C2 C10A 100.92(12) . . ?
C10A C2 C1 111.13(12) . . ?
C9 C4A' C4B' 108.23(14) . . ?
C4' C4A' C4B' 130.12(15) . . ?
C4' C4A' C9 121.65(16) . . ?
C24 C19 C6 117.12(14) . . ?
C20 C19 C6 124.79(14) . . ?
C20 C19 C24 118.09(14) . . ?
C1 C5 C4 105.85(12) . . ?
C1 C5 C6 60.59(10) . . ?
C25 C5 C1 127.61(13) . . ?
C25 C5 C4 114.50(13) . . ?
C25 C5 C6 125.62(13) . . ?
C6 C5 C4 111.49(13) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.50(15) . . ?
C15 C14 H14 119.7 . . ?
N10' C10A C4B' 123.66(14) . . ?
N10' C10A C2 126.23(14) . . ?
C4B' C10A C2 110.11(14) . . ?
C13 C18 H18 119.6 . . ?
C17 C18 C13 120.85(16) . . ?
C17 C18 H18 119.6 . . ?
C5A' C6' H6' 119.8 . . ?
C7' C6' C5A' 120.42(15) . . ?
C7' C6' H6' 119.8 . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.36(15) . . ?
C16 C15 H15 119.8 . . ?
N3 C4 C5 103.07(13) . . ?
N3 C4 H4 109.5 . . ?
N3 C4 C12 111.40(13) . . ?
C5 C4 H4 109.5 . . ?
C12 C4 C5 113.73(13) . . ?
C12 C4 H4 109.5 . . ?
C1 C6 H6 112.4 . . ?
C19 C6 C1 123.32(13) . . ?
C19 C6 C5 126.99(14) . . ?
C19 C6 H6 112.4 . . ?
C5 C6 C1 59.50(10) . . ?
C5 C6 H6 112.4 . . ?
C9A' C9' H9' 119.9 . . ?
C8' C9' C9A' 120.26(16) . . ?
C8' C9' H9' 119.9 . . ?
C25 C30 H30 119.7 . . ?
C29 C30 C25 120.61(16) . . ?
C29 C30 H30 119.7 . . ?
C19 C24 H24 119.4 . . ?
C23 C24 C19 121.10(16) . . ?
C23 C24 H24 119.4 . . ?
C6' C7' H7' 119.8 . . ?
C6' C7' C8' 120.39(14) . . ?
C8' C7' H7' 119.8 . . ?
C25 C26 H26 119.5 . . ?
C27 C26 C25 120.98(15) . . ?
C27 C26 H26 119.5 . . ?
C19 C20 H20 119.7 . . ?
C21 C20 C19 120.68(15) . . ?
C21 C20 H20 119.7 . . ?
C9' C8' C7' 120.51(16) . . ?
C9' C8' H8' 119.7 . . ?
C7' C8' H8' 119.7 . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.61(15) . . ?
C17 C16 H16 120.2 . . ?
C9 C1' H1' 120.4 . . ?
C9 C1' C2' 119.14(16) . . ?
C2' C1' H1' 120.4 . . ?
C18 C17 H17 119.9 . . ?
C16 C17 C18 120.13(16) . . ?
C16 C17 H17 119.9 . . ?
C4A' C4' H4' 121.0 . . ?
C4A' C4' C3' 117.92(16) . . ?
C3' C4' H4' 121.0 . . ?
C4' C3' H3' 119.5 . . ?
C4' C3' C2' 120.91(16) . . ?
C2' C3' H3' 119.5 . . ?
C20 C21 H21 119.7 . . ?
C22 C21 C20 120.64(16) . . ?
C22 C21 H21 119.7 . . ?
C26 C27 H27 119.9 . . ?
C26 C27 C28 120.23(17) . . ?
C28 C27 H27 119.9 . . ?
C30 C29 H29 119.5 . . ?
C28 C29 C30 120.95(16) . . ?
C28 C29 H29 119.5 . . ?
C4 C12 H12A 108.7 . . ?
C4 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C11 C12 C4 114.26(14) . . ?
C11 C12 H12A 108.7 . . ?
C11 C12 H12B 108.7 . . ?
C1' C2' C3' 120.72(16) . . ?
C1' C2' H2' 119.6 . . ?
C3' C2' H2' 119.6 . . ?
C1S O1S H1S 109.5 . . ?
C21 C22 H22 120.3 . . ?
C23 C22 C21 119.48(15) . . ?
C23 C22 H22 120.3 . . ?
C27 C28 H28 120.5 . . ?
C29 C28 C27 119.01(17) . . ?
C29 C28 H28 120.5 . . ?
C24 C23 H23 120.0 . . ?
C22 C23 C24 120.01(16) . . ?
C22 C23 H23 120.0 . . ?
O1A C11 C12 109.66(17) . . ?
O1A C11 H11A 109.7 . . ?
O1A C11 H11B 109.7 . . ?
C12 C11 H11A 109.7 . . ?
C12 C11 H11B 109.7 . . ?
C12 C11 H11C 107.7 . . ?
C12 C11 H11D 107.7 . . ?
H11A C11 H11B 108.2 . . ?
H11C C11 H11D 107.1 . . ?
O1 C11 C12 118.6(6) . . ?
O1 C11 H11C 107.7 . . ?
O1 C11 H11D 107.7 . . ?
O1S C1S H1SA 107.7 . . ?
O1S C1S H1SB 107.7 . . ?
O1S C1S H1SC 113.6 . . ?
O1S C1S H1SD 113.6 . . ?
O1S C1S C2S 118.4(3) . . ?
O1S C1S C3S 90.4(6) . . ?
H1SA C1S H1SB 107.1 . . ?
H1SC C1S H1SD 110.8 . . ?
C2S C1S H1SA 107.7 . . ?
C2S C1S H1SB 107.7 . . ?
C3S C1S H1SC 113.6 . . ?
C3S C1S H1SD 113.6 . . ?
C1S C2S H2SA 109.5 . . ?
C1S C2S H2SB 109.5 . . ?
C1S C2S H2SC 109.5 . . ?
H2SA C2S H2SB 109.5 . . ?
H2SA C2S H2SC 109.5 . . ?
H2SB C2S H2SC 109.5 . . ?
C1S C3S H3SA 109.5 . . ?
C1S C3S H3SB 109.5 . . ?
C1S C3S H3SC 109.5 . . ?
H3SA C3S H3SB 109.5 . . ?
H3SA C3S H3SC 109.5 . . ?
H3SB C3S H3SC 109.5 . . ?
C11 O1 H1 109.5 . . ?

_olex2_date_sample_data_collection 1488218796.35
_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_step-66
_database_code_depnum_ccdc_archive 'CCDC 1582653'
_audit_update_record             
;
2017-10-28 deposited with the CCDC.
2017-11-01 downloaded from the CCDC.
;
_audit_creation_date             2017-10-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C39 H29 N3 O2'
_chemical_formula_sum            'C39 H29 N3 O2'
_chemical_formula_weight         571.65
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C39 H29 N3 O2'
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                   9.8591(3)
_cell_length_b                   17.6789(6)
_cell_length_c                   16.9614(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.753(3)
_cell_angle_gamma                90
_cell_volume                     2935.83(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3806
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.3440
_cell_measurement_theta_min      2.7650
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98541
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14357
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.777
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -75.00   -1.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  -57.0000   90.0000 74

#__ type_ start__ end____ width___ exp.time_
  2 omega  -16.00   60.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -99.0000   60.0000 76

#__ type_ start__ end____ width___ exp.time_
  3 omega    0.00   48.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -38.0000  -90.0000 48

#__ type_ start__ end____ width___ exp.time_
  4 omega   34.00   84.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616 -178.0000  -60.0000 50
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0480568000
_diffrn_orient_matrix_UB_12      0.0162611000
_diffrn_orient_matrix_UB_13      0.0230546000
_diffrn_orient_matrix_UB_21      -0.0370871000
_diffrn_orient_matrix_UB_22      0.0147833000
_diffrn_orient_matrix_UB_23      -0.0349729000
_diffrn_orient_matrix_UB_31      -0.0395605000
_diffrn_orient_matrix_UB_32      -0.0335662000
_diffrn_orient_matrix_UB_33      -0.0042432000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5168
_reflns_number_total             6716
_reflns_odcompleteness_completeness 99.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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         0.292
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     438
_refine_ls_number_reflns         6716
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0520
_refine_ls_restrained_S_all      1.021
_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)+(0.0467P)²+1.5519P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1152
_refine_ls_wR_factor_ref         0.1249
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C44A) = Uanis(C44)
3. Others
 Sof(C42A)=Sof(H42A)=Sof(C43A)=Sof(H43A)=Sof(C44A)=Sof(H44A)=Sof(C45A)=
 Sof(H45A)=Sof(C46A)=Sof(H46A)=1-FVAR(1)
 Sof(C42)=Sof(H42)=Sof(C43)=Sof(H43)=Sof(C44)=Sof(H44)=Sof(C45)=Sof(H45)=
 Sof(C46)=Sof(H46)=FVAR(1)
4.a Riding coordinates:
 N3(H3)
4.b Ternary CH refined with riding coordinates:
 C4(H4), C6(H6)
4.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C42(H42), C43(H43),
 C44(H44), C45(H45), C46(H46), C52(H52), C53(H53), C54(H54), C55(H55), C56(H56),
  C1'(H1'), C2'(H2'), C3'(H3'), C4'(H4'), C9'(H9'), C10'(H10'), C11'(H11'),
 C12'(H12'), C42A(H42A), C43A(H43A), C44A(H44A), C45A(H45A), C46A(H46A)
4.d Idealised Me refined as rotating group:
 C62(H62A,H62B,H62C)
;
_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
O1 O 0.68095(13) 0.45425(7) 0.10206(7) 0.0313(3) Uani 1 1 d . . . . .
O2 O 0.73212(13) 0.57821(7) 0.09713(7) 0.0304(3) Uani 1 1 d . . . . .
N3 N 1.02913(14) 0.52747(8) 0.32709(8) 0.0229(3) Uani 1 1 d . . . . .
H3 H 1.0860 0.5401 0.3673 0.028 Uiso 1 1 d R . . . .
C1 C 0.85051(16) 0.45170(9) 0.26588(9) 0.0212(3) Uani 1 1 d . . . . .
C2 C 0.91202(16) 0.48517(9) 0.34755(9) 0.0215(3) Uani 1 1 d . . . . .
C4 C 1.08933(18) 0.48722(11) 0.26659(10) 0.0294(4) Uani 1 1 d . . . . .
H4 H 1.1407 0.4446 0.2921 0.035 Uiso 1 1 calc R . . . .
C5 C 0.96461(17) 0.45423(9) 0.21338(9) 0.0226(3) Uani 1 1 d . . . . .
C6 C 0.84647(17) 0.51104(9) 0.20054(9) 0.0233(3) Uani 1 1 d . . . . .
H6 H 0.8701 0.5622 0.2196 0.028 Uiso 1 1 calc R . . . .
C11 C 0.74251(17) 0.39268(9) 0.27212(9) 0.0232(3) Uani 1 1 d . . . . .
C12 C 0.77671(19) 0.31670(10) 0.28430(10) 0.0288(4) Uani 1 1 d . . . . .
H12 H 0.8649 0.3006 0.2788 0.035 Uiso 1 1 calc R . . . .
C13 C 0.6807(2) 0.26469(11) 0.30460(11) 0.0369(5) Uani 1 1 d . . . . .
H13 H 0.7048 0.2142 0.3126 0.044 Uiso 1 1 calc R . . . .
C14 C 0.5500(2) 0.28809(12) 0.31289(11) 0.0397(5) Uani 1 1 d . . . . .
H14 H 0.4859 0.2536 0.3271 0.048 Uiso 1 1 calc R . . . .
C15 C 0.5142(2) 0.36318(12) 0.29999(11) 0.0385(5) Uani 1 1 d . . . . .
H15 H 0.4255 0.3788 0.3049 0.046 Uiso 1 1 calc R . . . .
C16 C 0.60972(18) 0.41537(11) 0.27972(10) 0.0286(4) Uani 1 1 d . . . . .
H16 H 0.5846 0.4657 0.2712 0.034 Uiso 1 1 calc R . . . .
C41 C 1.18835(16) 0.53531(10) 0.22734(9) 0.0239(3) Uani 1 1 d . . . . .
C42 C 1.1828(2) 0.61272(12) 0.22998(13) 0.0295(5) Uani 0.811(3) 1 d . . P A 1
H42 H 1.1137 0.6364 0.2538 0.035 Uiso 0.811(3) 1 calc R . P A 1
C43 C 1.2798(3) 0.65619(14) 0.19724(14) 0.0362(6) Uani 0.811(3) 1 d . . P A 1
H43 H 1.2755 0.7086 0.2002 0.043 Uiso 0.811(3) 1 calc R . P A 1
C44 C 1.3823(4) 0.6228(2) 0.1605(2) 0.0344(7) Uani 0.811(3) 1 d . . P A 1
H44 H 1.4465 0.6520 0.1383 0.041 Uiso 0.811(3) 1 calc R . P A 1
C45 C 1.3872(2) 0.54292(15) 0.15750(16) 0.0341(6) Uani 0.811(3) 1 d . . P A 1
H45 H 1.4558 0.5191 0.1336 0.041 Uiso 0.811(3) 1 calc R . P A 1
C46 C 1.2902(2) 0.50013(13) 0.18991(12) 0.0275(5) Uani 0.811(3) 1 d . . P A 1
H46 H 1.2929 0.4476 0.1867 0.033 Uiso 0.811(3) 1 calc R . P A 1
C51 C 0.99744(17) 0.39803(10) 0.15242(10) 0.0257(4) Uani 1 1 d . . . . .
C52 C 1.06020(19) 0.32998(11) 0.17644(12) 0.0337(4) Uani 1 1 d . . . . .
H52 H 1.0738 0.3179 0.2302 0.040 Uiso 1 1 calc R . . . .
C53 C 1.1030(2) 0.27971(12) 0.12123(13) 0.0405(5) Uani 1 1 d . . . . .
H53 H 1.1461 0.2348 0.1383 0.049 Uiso 1 1 calc R . . . .
C54 C 1.0816(2) 0.29634(12) 0.04148(13) 0.0424(5) Uani 1 1 d . . . . .
H54 H 1.1087 0.2623 0.0046 0.051 Uiso 1 1 calc R . . . .
C55 C 1.0200(2) 0.36353(13) 0.01640(12) 0.0416(5) Uani 1 1 d . . . . .
H55 H 1.0052 0.3748 -0.0375 0.050 Uiso 1 1 calc R . . . .
C56 C 0.97983(19) 0.41452(11) 0.07162(11) 0.0315(4) Uani 1 1 d . . . . .
H56 H 0.9406 0.4603 0.0543 0.038 Uiso 1 1 calc R . . . .
C61 C 0.74446(17) 0.50838(9) 0.12924(10) 0.0239(3) Uani 1 1 d . . . . .
C62 C 0.6465(2) 0.58441(12) 0.02219(11) 0.0399(5) Uani 1 1 d . . . . .
H62A H 0.6832 0.5535 -0.0167 0.060 Uiso 1 1 calc GR . . . .
H62B H 0.6436 0.6362 0.0050 0.060 Uiso 1 1 calc GR . . . .
H62C H 0.5558 0.5677 0.0286 0.060 Uiso 1 1 calc GR . . . .
N7' N 0.85532(14) 0.37907(8) 0.52773(8) 0.0246(3) Uani 1 1 d . . . . .
N14' N 1.03657(14) 0.37007(8) 0.40634(8) 0.0237(3) Uani 1 1 d . . . . .
C1' C 0.74938(18) 0.60043(10) 0.36262(11) 0.0290(4) Uani 1 1 d . . . . .
H1' H 0.7751 0.6256 0.3186 0.035 Uiso 1 1 calc R . . . .
C2' C 0.65076(19) 0.63068(11) 0.40523(12) 0.0360(4) Uani 1 1 d . . . . .
H2' H 0.6096 0.6763 0.3891 0.043 Uiso 1 1 calc R . . . .
C3' C 0.61227(19) 0.59400(11) 0.47160(12) 0.0372(5) Uani 1 1 d . . . . .
H3' H 0.5446 0.6149 0.4987 0.045 Uiso 1 1 calc R . . . .
C4' C 0.67375(18) 0.52660(10) 0.49788(11) 0.0304(4) Uani 1 1 d . . . . .
H4' H 0.6504 0.5027 0.5432 0.037 Uiso 1 1 calc R . . . .
C5' C 0.77126(16) 0.49572(10) 0.45451(10) 0.0242(3) Uani 1 1 d . . . . .
C6' C 0.85445(16) 0.42744(9) 0.46896(9) 0.0212(3) Uani 1 1 d . . . . .
C8' C 0.95317(17) 0.32326(9) 0.52831(9) 0.0236(3) Uani 1 1 d . . . . .
C9' C 0.96647(18) 0.26983(10) 0.59043(10) 0.0282(4) Uani 1 1 d . . . . .
H9' H 0.9077 0.2717 0.6294 0.034 Uiso 1 1 calc R . . . .
C10' C 1.06534(19) 0.21519(10) 0.59369(10) 0.0310(4) Uani 1 1 d . . . . .
H10' H 1.0727 0.1799 0.6346 0.037 Uiso 1 1 calc R . . . .
C11' C 1.15560(19) 0.21202(10) 0.53579(11) 0.0327(4) Uani 1 1 d . . . . .
H11' H 1.2227 0.1748 0.5389 0.039 Uiso 1 1 calc R . . . .
C12' C 1.14585(18) 0.26307(10) 0.47485(11) 0.0295(4) Uani 1 1 d . . . . .
H12' H 1.2066 0.2605 0.4370 0.035 Uiso 1 1 calc R . . . .
C13' C 1.04427(17) 0.31962(9) 0.46906(10) 0.0244(4) Uani 1 1 d . . . . .
C15' C 0.94285(16) 0.42179(9) 0.40803(9) 0.0216(3) Uani 1 1 d . . . . .
C16' C 0.80907(16) 0.53189(9) 0.38694(9) 0.0226(3) Uani 1 1 d . . . . .
C42A C 1.2873(12) 0.5770(7) 0.2783(7) 0.052(3) Uani 0.189(3) 1 d . . P A 2
H42A H 1.2779 0.5804 0.3321 0.062 Uiso 0.189(3) 1 calc R . P A 2
C43A C 1.3964(11) 0.6122(7) 0.2499(7) 0.043(3) Uani 0.189(3) 1 d . . P A 2
H43A H 1.4614 0.6379 0.2841 0.052 Uiso 0.189(3) 1 calc R . P A 2
C44A C 1.406(2) 0.6090(13) 0.1766(12) 0.0344(7) Uani 0.189(3) 1 d . . P A 2
H44A H 1.4840 0.6305 0.1593 0.041 Uiso 0.189(3) 1 calc R . P A 2
C45A C 1.3173(18) 0.5781(10) 0.1221(8) 0.076(6) Uani 0.189(3) 1 d . . P A 2
H45A H 1.3295 0.5794 0.0686 0.091 Uiso 0.189(3) 1 calc R . P A 2
C46A C 1.2035(14) 0.5434(9) 0.1484(7) 0.067(5) Uani 0.189(3) 1 d . . P A 2
H46A H 1.1351 0.5251 0.1108 0.080 Uiso 0.189(3) 1 calc R . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C61 1.205(2) . ?
O2 C61 1.349(2) . ?
O2 C62 1.445(2) . ?
N3 C2 1.452(2) . ?
N3 C4 1.433(2) . ?
C1 C2 1.562(2) . ?
C1 C5 1.515(2) . ?
C1 C6 1.523(2) . ?
C1 C11 1.503(2) . ?
C2 C15' 1.525(2) . ?
C2 C16' 1.523(2) . ?
C4 C5 1.551(2) . ?
C4 C41 1.507(2) . ?
C5 C6 1.534(2) . ?
C5 C51 1.496(2) . ?
C6 C61 1.480(2) . ?
C11 C12 1.394(2) . ?
C11 C16 1.390(2) . ?
C12 C13 1.392(3) . ?
C13 C14 1.377(3) . ?
C14 C15 1.384(3) . ?
C15 C16 1.390(3) . ?
C41 C42 1.371(3) . ?
C41 C46 1.396(3) . ?
C41 C42A 1.430(11) . ?
C41 C46A 1.372(12) . ?
C42 C43 1.393(3) . ?
C43 C44 1.381(5) . ?
C44 C45 1.413(5) . ?
C45 C46 1.383(3) . ?
C51 C52 1.392(3) . ?
C51 C56 1.392(2) . ?
C52 C53 1.392(3) . ?
C53 C54 1.376(3) . ?
C54 C55 1.379(3) . ?
C55 C56 1.391(3) . ?
N7' C6' 1.313(2) . ?
N7' C8' 1.379(2) . ?
N14' C13' 1.383(2) . ?
N14' C15' 1.303(2) . ?
C1' C2' 1.385(3) . ?
C1' C16' 1.389(2) . ?
C2' C3' 1.390(3) . ?
C3' C4' 1.386(3) . ?
C4' C5' 1.389(2) . ?
C5' C6' 1.464(2) . ?
C5' C16' 1.401(2) . ?
C6' C15' 1.432(2) . ?
C8' C9' 1.410(2) . ?
C8' C13' 1.426(2) . ?
C9' C10' 1.369(3) . ?
C10' C11' 1.402(3) . ?
C11' C12' 1.367(3) . ?
C12' C13' 1.410(2) . ?
C42A C43A 1.379(16) . ?
C43A C44A 1.26(2) . ?
C44A C45A 1.32(3) . ?
C45A C46A 1.397(16) . ?

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
C61 O2 C62 116.12(14) . . ?
C4 N3 C2 108.87(13) . . ?
C5 C1 C2 105.81(13) . . ?
C5 C1 C6 60.64(10) . . ?
C6 C1 C2 111.02(13) . . ?
C11 C1 C2 113.89(13) . . ?
C11 C1 C5 129.99(14) . . ?
C11 C1 C6 124.83(13) . . ?
N3 C2 C1 102.71(12) . . ?
N3 C2 C15' 115.97(13) . . ?
N3 C2 C16' 114.55(13) . . ?
C15' C2 C1 110.13(13) . . ?
C16' C2 C1 112.67(13) . . ?
C16' C2 C15' 101.18(13) . . ?
N3 C4 C5 103.69(13) . . ?
N3 C4 C41 112.36(15) . . ?
C41 C4 C5 117.74(14) . . ?
C1 C5 C4 105.16(13) . . ?
C1 C5 C6 59.93(10) . . ?
C6 C5 C4 111.91(14) . . ?
C51 C5 C1 128.49(14) . . ?
C51 C5 C4 115.51(14) . . ?
C51 C5 C6 123.98(14) . . ?
C1 C6 C5 59.43(10) . . ?
C61 C6 C1 121.99(14) . . ?
C61 C6 C5 121.79(14) . . ?
C12 C11 C1 121.21(15) . . ?
C16 C11 C1 119.26(15) . . ?
C16 C11 C12 118.58(16) . . ?
C13 C12 C11 120.89(18) . . ?
C14 C13 C12 119.94(19) . . ?
C13 C14 C15 119.75(18) . . ?
C14 C15 C16 120.54(19) . . ?
C11 C16 C15 120.29(18) . . ?
C42 C41 C4 121.21(17) . . ?
C42 C41 C46 119.58(18) . . ?
C46 C41 C4 119.18(17) . . ?
C42A C41 C4 117.0(5) . . ?
C46A C41 C4 129.8(5) . . ?
C46A C41 C42A 113.1(7) . . ?
C41 C42 C43 120.4(2) . . ?
C44 C43 C42 121.2(3) . . ?
C43 C44 C45 118.2(3) . . ?
C46 C45 C44 120.3(3) . . ?
C45 C46 C41 120.3(2) . . ?
C52 C51 C5 119.76(15) . . ?
C52 C51 C56 117.97(16) . . ?
C56 C51 C5 121.95(16) . . ?
C51 C52 C53 120.96(18) . . ?
C54 C53 C52 120.1(2) . . ?
C53 C54 C55 119.90(18) . . ?
C54 C55 C56 120.05(19) . . ?
C55 C56 C51 121.00(19) . . ?
O1 C61 O2 123.65(15) . . ?
O1 C61 C6 127.61(15) . . ?
O2 C61 C6 108.73(14) . . ?
C6' N7' C8' 114.42(14) . . ?
C15' N14' C13' 114.24(14) . . ?
C2' C1' C16' 118.73(17) . . ?
C1' C2' C3' 121.18(17) . . ?
C4' C3' C2' 120.71(17) . . ?
C3' C4' C5' 118.11(17) . . ?
C4' C5' C6' 130.13(16) . . ?
C4' C5' C16' 121.41(16) . . ?
C16' C5' C6' 108.41(14) . . ?
N7' C6' C5' 128.16(15) . . ?
N7' C6' C15' 123.55(15) . . ?
C15' C6' C5' 108.26(14) . . ?
N7' C8' C9' 119.22(15) . . ?
N7' C8' C13' 121.69(15) . . ?
C9' C8' C13' 119.05(15) . . ?
C10' C9' C8' 120.42(16) . . ?
C9' C10' C11' 120.51(17) . . ?
C12' C11' C10' 120.62(17) . . ?
C11' C12' C13' 120.46(17) . . ?
N14' C13' C8' 122.06(15) . . ?
N14' C13' C12' 119.01(15) . . ?
C12' C13' C8' 118.94(15) . . ?
N14' C15' C2 125.92(14) . . ?
N14' C15' C6' 123.95(15) . . ?
C6' C15' C2 110.12(14) . . ?
C1' C16' C2 128.62(15) . . ?
C1' C16' C5' 119.82(16) . . ?
C5' C16' C2 111.51(14) . . ?
C43A C42A C41 121.7(10) . . ?
C44A C43A C42A 118.7(14) . . ?
C43A C44A C45A 126(2) . . ?
C44A C45A C46A 116.9(15) . . ?
C41 C46A C45A 122.8(10) . . ?

_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_step-65
_database_code_depnum_ccdc_archive 'CCDC 1582655'
_audit_update_record             
;
2017-10-28 deposited with the CCDC.
2017-11-01 downloaded from the CCDC.
;
_audit_creation_date             2017-10-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C43 H29 N3'
_chemical_formula_sum            'C43 H29 N3'
_chemical_formula_weight         587.69
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C43 H29 N3'
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'

_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                   9.7752(5)
_cell_length_b                   18.4617(8)
_cell_length_c                   18.0848(9)
_cell_angle_alpha                90
_cell_angle_beta                 102.389(5)
_cell_angle_gamma                90
_cell_volume                     3187.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6749
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.7260
_cell_measurement_theta_min      2.9370
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79868
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            21229
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.856
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   15.00   45.00   1.0000   16.2600
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   57.0000 -180.0000 30

#__ type_ start__ end____ width___ exp.time_
  2 omega   12.00   43.00   1.0000   16.2600
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   57.0000   90.0000 31

#__ type_ start__ end____ width___ exp.time_
  3 omega  -98.00  -37.00   1.0000   16.2600
omega____ theta____ kappa____ phi______ frames
    -      -22.4241 -178.0000 -150.0000 61

#__ type_ start__ end____ width___ exp.time_
  4 omega  -89.00  -45.00   1.0000   16.2600
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  178.0000  -90.0000 44

#__ type_ start__ end____ width___ exp.time_
  5 omega   -7.00   92.00   1.0000   16.2600
omega____ theta____ kappa____ phi______ frames
    -       23.3616   77.0000  120.0000 99

#__ type_ start__ end____ width___ exp.time_
  6 omega   26.00   60.00   1.0000   16.2600
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -99.0000    0.0000 34

#__ type_ start__ end____ width___ exp.time_
  7 omega   10.00   49.00   1.0000   16.2600
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   38.0000    0.0000 39
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0090491000
_diffrn_orient_matrix_UB_12      0.0381197000
_diffrn_orient_matrix_UB_13      0.0004171000
_diffrn_orient_matrix_UB_21      0.0164786000
_diffrn_orient_matrix_UB_22      -0.0004235000
_diffrn_orient_matrix_UB_23      0.0401444000
_diffrn_orient_matrix_UB_31      0.0718992000
_diffrn_orient_matrix_UB_32      -0.0046859000
_diffrn_orient_matrix_UB_33      -0.0003748000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6168
_reflns_number_total             7299
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         7299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0427
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0359P)²+1.4052P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.0987
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C42(H42), C43(H43),
 C44(H44), C45(H45), C46(H46), C52(H52), C53(H53), C54(H54), C55(H55), C56(H56),
  C62(H62), C63(H63), C64(H64), C65(H65), C66(H66), C1'(H1'), C2'(H2'),
 C3'(H3'), C4'(H4'), C9'(H9'), C10'(H10'), C11'(H11'), C12'(H12')
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N3 N 0.56930(10) 0.21469(5) 0.21738(6) 0.0145(2) Uani 1 1 d . . . . .
C1 C 0.64840(12) 0.32568(6) 0.28284(6) 0.0127(2) Uani 1 1 d . . . . .
C2 C 0.64747(12) 0.28154(6) 0.21049(7) 0.0137(2) Uani 1 1 d . . . . .
C4 C 0.50808(12) 0.22123(6) 0.27317(7) 0.0136(2) Uani 1 1 d . . . . .
C5 C 0.54233(12) 0.28893(6) 0.32093(7) 0.0135(2) Uani 1 1 d . . . . .
C6 C 0.69866(12) 0.28594(6) 0.35855(7) 0.0147(2) Uani 1 1 d . . . . .
H6 H 0.7423 0.2379 0.3528 0.018 Uiso 1 1 calc R . . . .
C11 C 0.68065(12) 0.40472(6) 0.27996(6) 0.0134(2) Uani 1 1 d . . . . .
C12 C 0.58096(13) 0.45945(7) 0.27313(7) 0.0179(3) Uani 1 1 d . . . . .
H12 H 0.4848 0.4474 0.2675 0.022 Uiso 1 1 calc R . . . .
C13 C 0.62123(13) 0.53193(7) 0.27447(8) 0.0218(3) Uani 1 1 d . . . . .
H13 H 0.5526 0.5689 0.2711 0.026 Uiso 1 1 calc R . . . .
C14 C 0.76060(13) 0.55051(7) 0.28071(7) 0.0199(3) Uani 1 1 d . . . . .
H14 H 0.7879 0.6000 0.2823 0.024 Uiso 1 1 calc R . . . .
C15 C 0.85976(13) 0.49608(7) 0.28461(7) 0.0191(3) Uani 1 1 d . . . . .
H15 H 0.9550 0.5083 0.2870 0.023 Uiso 1 1 calc R . . . .
C16 C 0.82028(12) 0.42399(7) 0.28510(7) 0.0161(2) Uani 1 1 d . . . . .
H16 H 0.8894 0.3872 0.2890 0.019 Uiso 1 1 calc R . . . .
C41 C 0.41518(12) 0.16278(6) 0.28944(7) 0.0148(2) Uani 1 1 d . . . . .
C42 C 0.39685(13) 0.15005(7) 0.36264(7) 0.0199(3) Uani 1 1 d . . . . .
H42 H 0.4410 0.1807 0.4030 0.024 Uiso 1 1 calc R . . . .
C43 C 0.31384(14) 0.09246(7) 0.37686(8) 0.0242(3) Uani 1 1 d . . . . .
H43 H 0.3017 0.0837 0.4268 0.029 Uiso 1 1 calc R . . . .
C44 C 0.24903(13) 0.04804(7) 0.31785(8) 0.0227(3) Uani 1 1 d . . . . .
H44 H 0.1935 0.0084 0.3276 0.027 Uiso 1 1 calc R . . . .
C45 C 0.26481(13) 0.06106(7) 0.24462(8) 0.0204(3) Uani 1 1 d . . . . .
H45 H 0.2190 0.0309 0.2043 0.024 Uiso 1 1 calc R . . . .
C46 C 0.34762(12) 0.11831(6) 0.23027(7) 0.0168(2) Uani 1 1 d . . . . .
H46 H 0.3583 0.1272 0.1801 0.020 Uiso 1 1 calc R . . . .
C51 C 0.42546(12) 0.32362(6) 0.34963(7) 0.0149(2) Uani 1 1 d . . . . .
C52 C 0.31020(13) 0.34807(6) 0.29579(7) 0.0172(2) Uani 1 1 d . . . . .
H52 H 0.3109 0.3445 0.2435 0.021 Uiso 1 1 calc R . . . .
C53 C 0.19469(13) 0.37748(7) 0.31799(8) 0.0210(3) Uani 1 1 d . . . . .
H53 H 0.1172 0.3943 0.2809 0.025 Uiso 1 1 calc R . . . .
C54 C 0.19233(14) 0.38229(7) 0.39432(8) 0.0252(3) Uani 1 1 d . . . . .
H54 H 0.1135 0.4026 0.4096 0.030 Uiso 1 1 calc R . . . .
C55 C 0.30542(15) 0.35733(8) 0.44812(8) 0.0261(3) Uani 1 1 d . . . . .
H55 H 0.3038 0.3604 0.5004 0.031 Uiso 1 1 calc R . . . .
C56 C 0.42158(14) 0.32779(7) 0.42601(7) 0.0208(3) Uani 1 1 d . . . . .
H56 H 0.4984 0.3104 0.4632 0.025 Uiso 1 1 calc R . . . .
C61 C 0.77370(13) 0.32712(7) 0.42636(7) 0.0167(2) Uani 1 1 d . . . . .
C62 C 0.73112(14) 0.39426(7) 0.44922(7) 0.0215(3) Uani 1 1 d . . . . .
H62 H 0.6438 0.4142 0.4242 0.026 Uiso 1 1 calc R . . . .
C63 C 0.81541(16) 0.43206(8) 0.50823(8) 0.0286(3) Uani 1 1 d . . . . .
H63 H 0.7855 0.4777 0.5231 0.034 Uiso 1 1 calc R . . . .
C64 C 0.94257(16) 0.40373(9) 0.54552(8) 0.0306(3) Uani 1 1 d . . . . .
H64 H 1.0007 0.4303 0.5851 0.037 Uiso 1 1 calc R . . . .
C65 C 0.98445(15) 0.33682(8) 0.52492(8) 0.0281(3) Uani 1 1 d . . . . .
H65 H 1.0705 0.3166 0.5513 0.034 Uiso 1 1 calc R . . . .
C66 C 0.90120(13) 0.29877(7) 0.46560(7) 0.0213(3) Uani 1 1 d . . . . .
H66 H 0.9314 0.2529 0.4516 0.026 Uiso 1 1 calc R . . . .
N7' N 0.62866(12) 0.36705(6) 0.02410(6) 0.0226(2) Uani 1 1 d . . . . .
N14' N 0.44368(11) 0.34390(5) 0.12632(6) 0.0168(2) Uani 1 1 d . . . . .
C1' C 0.90532(13) 0.23170(7) 0.23499(8) 0.0195(3) Uani 1 1 d . . . . .
H1' H 0.8994 0.2094 0.2816 0.023 Uiso 1 1 calc R . . . .
C2' C 1.02843(14) 0.22832(7) 0.20823(8) 0.0237(3) Uani 1 1 d . . . . .
H2' H 1.1075 0.2038 0.2371 0.028 Uiso 1 1 calc R . . . .
C3' C 1.03754(14) 0.26033(8) 0.13982(9) 0.0273(3) Uani 1 1 d . . . . .
H3' H 1.1226 0.2573 0.1226 0.033 Uiso 1 1 calc R . . . .
C4' C 0.92404(14) 0.29661(8) 0.09641(8) 0.0253(3) Uani 1 1 d . . . . .
H4' H 0.9302 0.3185 0.0497 0.030 Uiso 1 1 calc R . . . .
C5' C 0.80071(13) 0.30018(7) 0.12312(7) 0.0187(3) Uani 1 1 d . . . . .
C6' C 0.66570(13) 0.33359(7) 0.08927(7) 0.0180(3) Uani 1 1 d . . . . .
C8' C 0.49209(14) 0.39090(7) 0.00770(7) 0.0216(3) Uani 1 1 d . . . . .
C9' C 0.44067(16) 0.42723(8) -0.06153(8) 0.0298(3) Uani 1 1 d . . . . .
H9' H 0.5004 0.4346 -0.0960 0.036 Uiso 1 1 calc R . . . .
C10' C 0.30579(17) 0.45185(8) -0.07928(8) 0.0323(3) Uani 1 1 d . . . . .
H10' H 0.2727 0.4766 -0.1257 0.039 Uiso 1 1 calc R . . . .
C11' C 0.21545(16) 0.44084(8) -0.02923(8) 0.0296(3) Uani 1 1 d . . . . .
H11' H 0.1219 0.4582 -0.0422 0.036 Uiso 1 1 calc R . . . .
C12' C 0.26147(14) 0.40523(7) 0.03808(8) 0.0240(3) Uani 1 1 d . . . . .
H12' H 0.1996 0.3978 0.0713 0.029 Uiso 1 1 calc R . . . .
C13' C 0.40049(13) 0.37953(7) 0.05811(7) 0.0188(3) Uani 1 1 d . . . . .
C15' C 0.57331(12) 0.32241(6) 0.13981(7) 0.0151(2) Uani 1 1 d . . . . .
C16' C 0.79121(12) 0.26831(6) 0.19217(7) 0.0158(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N3 C2 1.4709(14) . ?
N3 C4 1.2846(15) . ?
C1 C2 1.5397(16) . ?
C1 C5 1.5220(16) . ?
C1 C6 1.5382(16) . ?
C1 C11 1.4962(16) . ?
C2 C15' 1.5267(16) . ?
C2 C16' 1.5309(16) . ?
C4 C5 1.5153(16) . ?
C4 C41 1.4799(16) . ?
C5 C6 1.5347(16) . ?
C5 C51 1.4964(16) . ?
C6 C61 1.4945(16) . ?
C11 C12 1.3907(16) . ?
C11 C16 1.3942(16) . ?
C12 C13 1.3934(17) . ?
C13 C14 1.3859(18) . ?
C14 C15 1.3874(18) . ?
C15 C16 1.3862(17) . ?
C41 C42 1.3935(17) . ?
C41 C46 1.3971(17) . ?
C42 C43 1.3944(18) . ?
C43 C44 1.3865(19) . ?
C44 C45 1.3867(19) . ?
C45 C46 1.3891(17) . ?
C51 C52 1.3967(17) . ?
C51 C56 1.3920(17) . ?
C52 C53 1.3876(17) . ?
C53 C54 1.388(2) . ?
C54 C55 1.385(2) . ?
C55 C56 1.3934(18) . ?
C61 C62 1.3980(18) . ?
C61 C66 1.3969(17) . ?
C62 C63 1.3884(18) . ?
C63 C64 1.383(2) . ?
C64 C65 1.378(2) . ?
C65 C66 1.3899(19) . ?
N7' C6' 1.3111(17) . ?
N7' C8' 1.3763(18) . ?
N14' C13' 1.3818(16) . ?
N14' C15' 1.2999(16) . ?
C1' C2' 1.3916(17) . ?
C1' C16' 1.3893(17) . ?
C2' C3' 1.391(2) . ?
C3' C4' 1.386(2) . ?
C4' C5' 1.3931(17) . ?
C5' C6' 1.4664(18) . ?
C5' C16' 1.4014(18) . ?
C6' C15' 1.4311(17) . ?
C8' C9' 1.4141(19) . ?
C8' C13' 1.4237(18) . ?
C9' C10' 1.366(2) . ?
C10' C11' 1.408(2) . ?
C11' C12' 1.3717(19) . ?
C12' C13' 1.4113(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N3 C2 109.01(9) . . ?
C5 C1 C2 105.56(9) . . ?
C5 C1 C6 60.19(7) . . ?
C6 C1 C2 116.53(9) . . ?
C11 C1 C2 116.71(10) . . ?
C11 C1 C5 128.28(10) . . ?
C11 C1 C6 117.82(10) . . ?
N3 C2 C1 106.30(9) . . ?
N3 C2 C15' 108.88(9) . . ?
N3 C2 C16' 113.70(9) . . ?
C15' C2 C1 111.41(9) . . ?
C15' C2 C16' 100.99(9) . . ?
C16' C2 C1 115.47(10) . . ?
N3 C4 C5 116.23(10) . . ?
N3 C4 C41 119.79(10) . . ?
C41 C4 C5 123.93(10) . . ?
C1 C5 C6 60.43(7) . . ?
C4 C5 C1 101.44(9) . . ?
C4 C5 C6 107.48(9) . . ?
C51 C5 C1 127.68(10) . . ?
C51 C5 C4 117.32(10) . . ?
C51 C5 C6 128.55(10) . . ?
C5 C6 C1 59.38(7) . . ?
C61 C6 C1 119.65(10) . . ?
C61 C6 C5 127.76(10) . . ?
C12 C11 C1 124.25(10) . . ?
C12 C11 C16 118.55(11) . . ?
C16 C11 C1 117.20(10) . . ?
C11 C12 C13 120.40(11) . . ?
C14 C13 C12 120.55(11) . . ?
C13 C14 C15 119.25(11) . . ?
C16 C15 C14 120.22(11) . . ?
C15 C16 C11 120.95(11) . . ?
C42 C41 C4 121.42(11) . . ?
C42 C41 C46 119.50(11) . . ?
C46 C41 C4 119.06(11) . . ?
C41 C42 C43 120.15(12) . . ?
C44 C43 C42 119.80(12) . . ?
C43 C44 C45 120.43(12) . . ?
C44 C45 C46 119.93(12) . . ?
C45 C46 C41 120.18(12) . . ?
C52 C51 C5 117.27(11) . . ?
C56 C51 C5 123.60(11) . . ?
C56 C51 C52 118.96(11) . . ?
C53 C52 C51 120.64(12) . . ?
C52 C53 C54 120.05(12) . . ?
C55 C54 C53 119.74(12) . . ?
C54 C55 C56 120.34(13) . . ?
C51 C56 C55 120.26(12) . . ?
C62 C61 C6 124.66(11) . . ?
C66 C61 C6 116.98(11) . . ?
C66 C61 C62 118.15(12) . . ?
C63 C62 C61 120.52(13) . . ?
C64 C63 C62 120.51(14) . . ?
C65 C64 C63 119.68(13) . . ?
C64 C65 C66 120.21(13) . . ?
C65 C66 C61 120.90(13) . . ?
C6' N7' C8' 114.36(11) . . ?
C15' N14' C13' 114.31(11) . . ?
C16' C1' C2' 118.60(12) . . ?
C3' C2' C1' 121.03(13) . . ?
C4' C3' C2' 120.84(12) . . ?
C3' C4' C5' 118.26(13) . . ?
C4' C5' C6' 130.05(12) . . ?
C4' C5' C16' 121.12(12) . . ?
C16' C5' C6' 108.83(11) . . ?
N7' C6' C5' 128.59(11) . . ?
N7' C6' C15' 123.49(12) . . ?
C15' C6' C5' 107.91(11) . . ?
N7' C8' C9' 119.12(12) . . ?
N7' C8' C13' 121.94(12) . . ?
C9' C8' C13' 118.94(13) . . ?
C10' C9' C8' 120.51(14) . . ?
C9' C10' C11' 120.50(13) . . ?
C12' C11' C10' 120.53(13) . . ?
C11' C12' C13' 120.21(13) . . ?
N14' C13' C8' 121.88(11) . . ?
N14' C13' C12' 118.82(12) . . ?
C12' C13' C8' 119.30(12) . . ?
N14' C15' C2 125.21(11) . . ?
N14' C15' C6' 124.02(11) . . ?
C6' C15' C2 110.77(10) . . ?
C1' C16' C2 128.42(11) . . ?
C1' C16' C5' 120.15(11) . . ?
C5' C16' C2 111.42(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_step-67
_database_code_depnum_ccdc_archive 'CCDC 1582654'
_audit_update_record             
;
2017-10-28 deposited with the CCDC.
2017-11-01 downloaded from the CCDC.
;
_audit_creation_date             2017-10-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C44 H31 N3 O'
_chemical_formula_sum            'C44 H31 N3 O'
_chemical_formula_weight         617.72
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C44 H31 N3 O'
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                   9.9057(3)
_cell_length_b                   18.2185(5)
_cell_length_c                   17.9256(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.694(3)
_cell_angle_gamma                90
_cell_volume                     3224.13(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5095
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.7500
_cell_measurement_theta_min      3.0330
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15480
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         2.947
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   15.00   40.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   57.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
  2 omega  -51.00    6.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   77.0000   30.0000 57

#__ type_ start__ end____ width___ exp.time_
  3 omega  -71.00  -35.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241 -178.0000  -60.0000 36

#__ type_ start__ end____ width___ exp.time_
  4 omega  -31.00   -1.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   57.0000  -30.0000 30

#__ type_ start__ end____ width___ exp.time_
  5 omega   -6.00   90.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616   77.0000 -150.0000 96
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0075337000
_diffrn_orient_matrix_UB_12      -0.0334810000
_diffrn_orient_matrix_UB_13      0.0194280000
_diffrn_orient_matrix_UB_21      -0.0143683000
_diffrn_orient_matrix_UB_22      0.0198505000
_diffrn_orient_matrix_UB_23      0.0324377000
_diffrn_orient_matrix_UB_31      -0.0699873000
_diffrn_orient_matrix_UB_32      -0.0004738000
_diffrn_orient_matrix_UB_33      -0.0121552000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5862
_reflns_number_total             7300
_reflns_odcompleteness_completeness 98.22
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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         0.347
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     434
_refine_ls_number_reflns         7300
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0442
_refine_ls_restrained_S_all      1.014
_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)+(0.0365P)²+1.5857P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.1036
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C42(H42), C43(H43),
 C45(H45), C46(H46), C52(H52), C53(H53), C54(H54), C55(H55), C56(H56), C62(H62),
  C63(H63), C64(H64), C65(H65), C66(H66), C1'(H1'), C2'(H2'), C3'(H3'),
 C4'(H4'), C9'(H9'), C10'(H10'), C11'(H11'), C12'(H12')
2.c Idealised Me refined as rotating group:
 C47(H47A,H47B,H47C)
;
_atom_sites_solution_hydrogens   geom
_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
O1 O -0.04297(11) 0.40449(6) 0.00291(6) 0.0238(2) Uani 1 1 d . . . . .
N3 N 0.45586(11) 0.28054(6) 0.20897(6) 0.0154(2) Uani 1 1 d . . . . .
C1 C 0.53502(13) 0.33454(7) 0.32784(7) 0.0134(3) Uani 1 1 d . . . . .
C2 C 0.55177(13) 0.26894(7) 0.27525(7) 0.0145(3) Uani 1 1 d . . . . .
C4 C 0.37325(13) 0.33215(7) 0.22314(7) 0.0142(3) Uani 1 1 d . . . . .
C5 C 0.40613(13) 0.37356(7) 0.29576(7) 0.0140(3) Uani 1 1 d . . . . .
C6 C 0.54557(13) 0.40976(7) 0.29015(8) 0.0150(3) Uani 1 1 d . . . . .
H6 H 0.5767 0.4053 0.2387 0.018 Uiso 1 1 calc R . . . .
C11 C 0.58586(13) 0.32527(7) 0.40814(7) 0.0139(3) Uani 1 1 d . . . . .
C12 C 0.72173(14) 0.34176(8) 0.42895(8) 0.0167(3) Uani 1 1 d . . . . .
H12 H 0.7783 0.3585 0.3922 0.020 Uiso 1 1 calc R . . . .
C13 C 0.77462(15) 0.33392(8) 0.50237(8) 0.0200(3) Uani 1 1 d . . . . .
H13 H 0.8668 0.3459 0.5158 0.024 Uiso 1 1 calc R . . . .
C14 C 0.69334(15) 0.30864(8) 0.55652(8) 0.0227(3) Uani 1 1 d . . . . .
H14 H 0.7294 0.3039 0.6071 0.027 Uiso 1 1 calc R . . . .
C15 C 0.55965(16) 0.29040(8) 0.53649(8) 0.0227(3) Uani 1 1 d . . . . .
H15 H 0.5043 0.2722 0.5732 0.027 Uiso 1 1 calc R . . . .
C16 C 0.50588(14) 0.29865(8) 0.46265(8) 0.0180(3) Uani 1 1 d . . . . .
H16 H 0.4140 0.2860 0.4494 0.022 Uiso 1 1 calc R . . . .
C41 C 0.25919(13) 0.34994(7) 0.16798(7) 0.0147(3) Uani 1 1 d . . . . .
C42 C 0.20245(14) 0.42019(8) 0.16271(8) 0.0178(3) Uani 1 1 d . . . . .
H42 H 0.2327 0.4569 0.1978 0.021 Uiso 1 1 calc R . . . .
C43 C 0.10265(15) 0.43648(8) 0.10681(8) 0.0197(3) Uani 1 1 d . . . . .
H43 H 0.0661 0.4847 0.1028 0.024 Uiso 1 1 calc R . . . .
C44 C 0.05537(14) 0.38239(8) 0.05627(8) 0.0176(3) Uani 1 1 d . . . . .
C45 C 0.10939(14) 0.31190(8) 0.06117(8) 0.0181(3) Uani 1 1 d . . . . .
H45 H 0.0768 0.2748 0.0270 0.022 Uiso 1 1 calc R . . . .
C46 C 0.21159(14) 0.29653(8) 0.11667(8) 0.0168(3) Uani 1 1 d . . . . .
H46 H 0.2498 0.2487 0.1197 0.020 Uiso 1 1 calc R . . . .
C47 C -0.11445(17) 0.34916(9) -0.03999(10) 0.0314(4) Uani 1 1 d . . . . .
H47A H -0.1877 0.3717 -0.0722 0.047 Uiso 1 1 calc GR . . . .
H47B H -0.1527 0.3138 -0.0063 0.047 Uiso 1 1 calc GR . . . .
H47C H -0.0522 0.3238 -0.0711 0.047 Uiso 1 1 calc GR . . . .
C51 C 0.29149(13) 0.40055(8) 0.33763(8) 0.0156(3) Uani 1 1 d . . . . .
C52 C 0.20101(14) 0.34846(8) 0.36187(8) 0.0186(3) Uani 1 1 d . . . . .
H52 H 0.2186 0.2977 0.3557 0.022 Uiso 1 1 calc R . . . .
C53 C 0.08563(15) 0.37041(9) 0.39491(9) 0.0231(3) Uani 1 1 d . . . . .
H53 H 0.0251 0.3346 0.4114 0.028 Uiso 1 1 calc R . . . .
C54 C 0.05835(15) 0.44451(9) 0.40401(9) 0.0250(3) Uani 1 1 d . . . . .
H54 H -0.0207 0.4595 0.4266 0.030 Uiso 1 1 calc R . . . .
C55 C 0.14742(15) 0.49658(9) 0.37989(9) 0.0236(3) Uani 1 1 d . . . . .
H55 H 0.1292 0.5473 0.3861 0.028 Uiso 1 1 calc R . . . .
C56 C 0.26354(14) 0.47491(8) 0.34659(8) 0.0195(3) Uani 1 1 d . . . . .
H56 H 0.3237 0.5109 0.3300 0.023 Uiso 1 1 calc R . . . .
C61 C 0.60832(14) 0.47413(7) 0.33107(8) 0.0166(3) Uani 1 1 d . . . . .
C62 C 0.58582(15) 0.49549(8) 0.40387(9) 0.0211(3) Uani 1 1 d . . . . .
H62 H 0.5187 0.4712 0.4297 0.025 Uiso 1 1 calc R . . . .
C63 C 0.66106(16) 0.55208(8) 0.43888(9) 0.0262(3) Uani 1 1 d . . . . .
H63 H 0.6446 0.5661 0.4884 0.031 Uiso 1 1 calc R . . . .
C64 C 0.75937(18) 0.58804(9) 0.40246(10) 0.0311(4) Uani 1 1 d . . . . .
H64 H 0.8113 0.6262 0.4269 0.037 Uiso 1 1 calc R . . . .
C65 C 0.78159(18) 0.56793(9) 0.32988(10) 0.0329(4) Uani 1 1 d . . . . .
H65 H 0.8485 0.5927 0.3043 0.040 Uiso 1 1 calc R . . . .
C66 C 0.70666(16) 0.51198(8) 0.29463(9) 0.0241(3) Uani 1 1 d . . . . .
H66 H 0.7223 0.4990 0.2447 0.029 Uiso 1 1 calc R . . . .
N7' N 0.62027(12) 0.07806(6) 0.33480(7) 0.0180(3) Uani 1 1 d . . . . .
N14' N 0.39916(11) 0.18063(6) 0.33546(7) 0.0171(2) Uani 1 1 d . . . . .
C1' C 0.78839(14) 0.30299(8) 0.22896(8) 0.0185(3) Uani 1 1 d . . . . .
H1' H 0.7612 0.3514 0.2150 0.022 Uiso 1 1 calc R . . . .
C2' C 0.92010(15) 0.27952(8) 0.22159(9) 0.0222(3) Uani 1 1 d . . . . .
H2' H 0.9840 0.3127 0.2036 0.027 Uiso 1 1 calc R . . . .
C3' C 0.95968(15) 0.20823(9) 0.24017(9) 0.0251(3) Uani 1 1 d . . . . .
H3' H 1.0501 0.1933 0.2345 0.030 Uiso 1 1 calc R . . . .
C4' C 0.86884(15) 0.15853(8) 0.26694(9) 0.0220(3) Uani 1 1 d . . . . .
H4' H 0.8955 0.1095 0.2785 0.026 Uiso 1 1 calc R . . . .
C5' C 0.73746(14) 0.18249(8) 0.27634(8) 0.0162(3) Uani 1 1 d . . . . .
C6' C 0.62470(13) 0.14509(7) 0.30859(7) 0.0148(3) Uani 1 1 d . . . . .
C8' C 0.50008(14) 0.06015(8) 0.36433(8) 0.0178(3) Uani 1 1 d . . . . .
C9' C 0.48513(16) -0.01038(8) 0.39523(8) 0.0216(3) Uani 1 1 d . . . . .
H9' H 0.5574 -0.0447 0.3954 0.026 Uiso 1 1 calc R . . . .
C10' C 0.36686(16) -0.02965(8) 0.42495(8) 0.0236(3) Uani 1 1 d . . . . .
H10' H 0.3573 -0.0775 0.4449 0.028 Uiso 1 1 calc R . . . .
C11' C 0.25931(16) 0.02093(9) 0.42607(9) 0.0251(3) Uani 1 1 d . . . . .
H11' H 0.1784 0.0072 0.4475 0.030 Uiso 1 1 calc R . . . .
C12' C 0.27074(15) 0.08979(8) 0.39646(9) 0.0229(3) Uani 1 1 d . . . . .
H12' H 0.1976 0.1235 0.3972 0.028 Uiso 1 1 calc R . . . .
C13' C 0.39116(14) 0.11089(8) 0.36481(8) 0.0175(3) Uani 1 1 d . . . . .
C15' C 0.51488(13) 0.19576(7) 0.30950(7) 0.0144(3) Uani 1 1 d . . . . .
C16' C 0.69717(14) 0.25428(8) 0.25715(7) 0.0148(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C44 1.3688(16) . ?
O1 C47 1.4212(18) . ?
N3 C2 1.4746(17) . ?
N3 C4 1.2854(17) . ?
C1 C2 1.5395(18) . ?
C1 C5 1.5317(18) . ?
C1 C6 1.5354(18) . ?
C1 C11 1.4952(18) . ?
C2 C15' 1.5247(19) . ?
C2 C16' 1.5257(18) . ?
C4 C5 1.5167(18) . ?
C4 C41 1.4753(18) . ?
C5 C6 1.5413(18) . ?
C5 C51 1.4946(18) . ?
C6 C61 1.4915(19) . ?
C11 C12 1.3995(19) . ?
C11 C16 1.3944(19) . ?
C12 C13 1.383(2) . ?
C13 C14 1.389(2) . ?
C14 C15 1.384(2) . ?
C15 C16 1.394(2) . ?
C41 C42 1.3979(19) . ?
C41 C46 1.3943(19) . ?
C42 C43 1.381(2) . ?
C43 C44 1.394(2) . ?
C44 C45 1.391(2) . ?
C45 C46 1.3885(19) . ?
C51 C52 1.399(2) . ?
C51 C56 1.3947(19) . ?
C52 C53 1.389(2) . ?
C53 C54 1.389(2) . ?
C54 C55 1.388(2) . ?
C55 C56 1.396(2) . ?
C61 C62 1.397(2) . ?
C61 C66 1.398(2) . ?
C62 C63 1.391(2) . ?
C63 C64 1.381(2) . ?
C64 C65 1.386(3) . ?
C65 C66 1.383(2) . ?
N7' C6' 1.3105(18) . ?
N7' C8' 1.3810(18) . ?
N14' C13' 1.3799(18) . ?
N14' C15' 1.3015(17) . ?
C1' C2' 1.389(2) . ?
C1' C16' 1.3907(19) . ?
C2' C3' 1.389(2) . ?
C3' C4' 1.389(2) . ?
C4' C5' 1.3960(19) . ?
C5' C6' 1.4669(19) . ?
C5' C16' 1.4020(19) . ?
C6' C15' 1.4278(18) . ?
C8' C9' 1.412(2) . ?
C8' C13' 1.421(2) . ?
C9' C10' 1.372(2) . ?
C10' C11' 1.410(2) . ?
C11' C12' 1.371(2) . ?
C12' C13' 1.415(2) . ?

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
C44 O1 C47 117.65(12) . . ?
C4 N3 C2 108.92(11) . . ?
C5 C1 C2 104.99(11) . . ?
C5 C1 C6 60.34(9) . . ?
C6 C1 C2 114.13(11) . . ?
C11 C1 C2 117.21(11) . . ?
C11 C1 C5 128.21(11) . . ?
C11 C1 C6 119.66(11) . . ?
N3 C2 C1 106.71(10) . . ?
N3 C2 C15' 106.86(11) . . ?
N3 C2 C16' 114.26(11) . . ?
C15' C2 C1 113.01(11) . . ?
C15' C2 C16' 101.19(11) . . ?
C16' C2 C1 114.65(11) . . ?
N3 C4 C5 115.98(12) . . ?
N3 C4 C41 119.55(12) . . ?
C41 C4 C5 124.39(12) . . ?
C1 C5 C6 59.95(8) . . ?
C4 C5 C1 101.84(10) . . ?
C4 C5 C6 106.71(11) . . ?
C51 C5 C1 127.47(12) . . ?
C51 C5 C4 118.42(11) . . ?
C51 C5 C6 127.86(12) . . ?
C1 C6 C5 59.71(8) . . ?
C61 C6 C1 121.73(11) . . ?
C61 C6 C5 130.08(12) . . ?
C12 C11 C1 118.24(12) . . ?
C16 C11 C1 123.23(12) . . ?
C16 C11 C12 118.49(13) . . ?
C13 C12 C11 120.83(13) . . ?
C12 C13 C14 120.18(14) . . ?
C15 C14 C13 119.68(14) . . ?
C14 C15 C16 120.25(14) . . ?
C15 C16 C11 120.53(14) . . ?
C42 C41 C4 121.88(12) . . ?
C46 C41 C4 119.20(12) . . ?
C46 C41 C42 118.81(13) . . ?
C43 C42 C41 120.38(13) . . ?
C42 C43 C44 120.15(13) . . ?
O1 C44 C43 115.37(13) . . ?
O1 C44 C45 124.31(13) . . ?
C45 C44 C43 120.31(13) . . ?
C46 C45 C44 119.04(13) . . ?
C45 C46 C41 121.28(13) . . ?
C52 C51 C5 117.73(12) . . ?
C56 C51 C5 122.92(13) . . ?
C56 C51 C52 119.01(13) . . ?
C53 C52 C51 120.53(14) . . ?
C52 C53 C54 120.32(14) . . ?
C55 C54 C53 119.53(14) . . ?
C54 C55 C56 120.46(14) . . ?
C51 C56 C55 120.16(14) . . ?
C62 C61 C6 125.91(13) . . ?
C62 C61 C66 117.99(13) . . ?
C66 C61 C6 115.86(13) . . ?
C63 C62 C61 120.49(14) . . ?
C64 C63 C62 120.70(15) . . ?
C63 C64 C65 119.37(15) . . ?
C66 C65 C64 120.20(15) . . ?
C65 C66 C61 121.23(15) . . ?
C6' N7' C8' 114.38(12) . . ?
C15' N14' C13' 114.27(12) . . ?
C2' C1' C16' 118.76(13) . . ?
C3' C2' C1' 120.91(14) . . ?
C2' C3' C4' 120.93(14) . . ?
C3' C4' C5' 118.32(14) . . ?
C4' C5' C6' 130.53(13) . . ?
C4' C5' C16' 120.77(13) . . ?
C16' C5' C6' 108.63(12) . . ?
N7' C6' C5' 128.54(12) . . ?
N7' C6' C15' 123.40(13) . . ?
C15' C6' C5' 108.03(12) . . ?
N7' C8' C9' 119.13(13) . . ?
N7' C8' C13' 121.82(13) . . ?
C9' C8' C13' 119.05(13) . . ?
C10' C9' C8' 120.37(14) . . ?
C9' C10' C11' 120.57(14) . . ?
C12' C11' C10' 120.41(14) . . ?
C11' C12' C13' 120.20(14) . . ?
N14' C13' C8' 121.96(13) . . ?
N14' C13' C12' 118.65(13) . . ?
C12' C13' C8' 119.39(13) . . ?
N14' C15' C2 125.19(12) . . ?
N14' C15' C6' 124.14(13) . . ?
C6' C15' C2 110.66(11) . . ?
C1' C16' C2 128.19(12) . . ?
C1' C16' C5' 120.27(13) . . ?
C5' C16' C2 111.46(12) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
