# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

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

data_F197
_database_code_depnum_ccdc_archive 'CCDC 1502355'
_audit_update_record             
;
2016-09-02 deposited with the CCDC.
2018-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H14 N2 O2'
_chemical_formula_weight         314.33

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

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

_cell_length_a                   16.9028(8)
_cell_length_b                   16.5253(7)
_cell_length_c                   9.9901(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2790.5(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9940
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      28.29

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_F_000             1312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7144
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Microfocusing Source'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37328
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.410
_diffrn_reflns_theta_max         28.353
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6914
_reflns_number_gt                6152
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.884
_reflns_Friedel_fraction_max     0.988
_reflns_Friedel_fraction_full    1.000

_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. 
 One of the molecules was disordered into two position with 
 occupancy ratio=50:50. Restraints in bond lengths and thermal 
 parameters were applied to the disordered atoms.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0507P)²+0.6384P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2666 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.3(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6914
_refine_ls_number_parameters     625
_refine_ls_number_restraints     1106
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0592
_refine_ls_wR_factor_ref         0.1482
_refine_ls_wR_factor_gt          0.1431
_refine_ls_goodness_of_fit_ref   1.597
_refine_ls_restrained_S_all      1.666
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3A O 0.7211(4) 0.6061(3) -0.0628(6) 0.0308(9) Uani 0.5 1 d . U P A 1
O4A O 0.3764(3) 0.5855(3) 0.3129(6) 0.0285(9) Uani 0.5 1 d . U P A 1
N3A N 0.6583(4) 0.5703(4) 0.1396(6) 0.0244(9) Uani 0.5 1 d D U P A 1
N4A N 0.5145(4) 0.5568(4) 0.2936(7) 0.0240(9) Uani 0.5 1 d D U P A 1
C22A C 0.6461(6) 0.6631(5) -0.2521(9) 0.0261(10) Uani 0.5 1 d . U P A 1
H22A H 0.6930 0.6683 -0.3037 0.031 Uiso 0.5 1 calc R U P A 1
C23A C 0.5762(6) 0.6876(4) -0.3043(8) 0.0287(10) Uani 0.5 1 d . U P A 1
H23A H 0.5754 0.7084 -0.3929 0.034 Uiso 0.5 1 calc R U P A 1
C32A C 0.3629(5) 0.7076(4) -0.2046(9) 0.0304(10) Uani 0.5 1 d . U P A 1
H32A H 0.3139 0.7279 -0.2371 0.036 Uiso 0.5 1 calc R U P A 1
C33A C 0.4286(6) 0.7116(5) -0.2843(8) 0.0261(11) Uani 0.5 1 d . U P A 1
H33A H 0.4245 0.7327 -0.3725 0.031 Uiso 0.5 1 calc R U P A 1
C37A C 0.4542(5) 0.5941(5) 0.3732(8) 0.0271(10) Uani 0.5 1 d . U P A 1
H37A H 0.4664 0.6523 0.3840 0.032 Uiso 0.5 1 calc R U P A 1
H37B H 0.4538 0.5691 0.4632 0.032 Uiso 0.5 1 calc R U P A 1
C38A C 0.5917(4) 0.5493(5) 0.3542(7) 0.0241(9) Uani 0.5 1 d D U P A 1
H38A H 0.5884 0.5131 0.4329 0.029 Uiso 0.5 1 calc R U P A 1
H38B H 0.6098 0.6031 0.3853 0.029 Uiso 0.5 1 calc R U P A 1
C21A C 0.6504(5) 0.6291(5) -0.1184(8) 0.0254(9) Uani 0.5 1 d . U P A 1
C24A C 0.5056(5) 0.6834(4) -0.2336(8) 0.0243(9) Uani 0.5 1 d . U P A 1
C25A C 0.5093(5) 0.6518(4) -0.1028(11) 0.0202(9) Uani 0.5 1 d . U P A 1
C26A C 0.5802(7) 0.6233(8) -0.0454(11) 0.0207(9) Uani 0.5 1 d . U P A 1
C27A C 0.5831(9) 0.5933(10) 0.0893(14) 0.0209(9) Uani 0.5 1 d . U P A 1
C28A C 0.5160(6) 0.5898(8) 0.1618(15) 0.0213(9) Uani 0.5 1 d . U P A 1
C29A C 0.4418(2) 0.6180(4) 0.1066(5) 0.0214(8) Uani 0.5 1 d G U P A 1
C30A C 0.4384(3) 0.6486(4) -0.0228(5) 0.0219(9) Uani 0.5 1 d G U P A 1
C31A C 0.3665(3) 0.6741(3) -0.0756(4) 0.0271(9) Uani 0.5 1 d G U P A 1
C34A C 0.2980(2) 0.6689(3) 0.0010(5) 0.0259(10) Uani 0.5 1 d G U P A 1
H34A H 0.2489 0.6863 -0.0352 0.031 Uiso 0.5 1 calc R U P A 1
C35A C 0.3014(2) 0.6383(3) 0.1304(5) 0.0298(10) Uani 0.5 1 d G U P A 1
H35A H 0.2547 0.6347 0.1828 0.036 Uiso 0.5 1 calc R U P A 1
C36A C 0.3733(3) 0.6128(3) 0.1833(4) 0.0260(9) Uani 0.5 1 d G U P A 1
C39A C 0.6508(4) 0.5152(4) 0.2541(7) 0.0246(10) Uani 0.5 1 d D U P A 1
H39A H 0.7029 0.5083 0.2978 0.030 Uiso 0.5 1 calc R U P A 1
H39B H 0.6327 0.4614 0.2228 0.030 Uiso 0.5 1 calc R U P A 1
C40A C 0.7117(4) 0.5448(5) 0.0363(8) 0.0280(9) Uani 0.5 1 d D U P A 1
H40A H 0.7639 0.5320 0.0762 0.034 Uiso 0.5 1 calc R U P A 1
H40B H 0.6911 0.4949 -0.0063 0.034 Uiso 0.5 1 calc R U P A 1
O3B O 0.7296(3) 0.5942(3) -0.0022(6) 0.0266(8) Uani 0.5 1 d . U P B 2
O4B O 0.3494(4) 0.6035(4) 0.2644(6) 0.0352(10) Uani 0.5 1 d . U P B 2
N3B N 0.6423(4) 0.5703(4) 0.1814(6) 0.0251(9) Uani 0.5 1 d D U P B 2
N4B N 0.4853(4) 0.5684(4) 0.2891(8) 0.0275(9) Uani 0.5 1 d D U P B 2
C21B C 0.6690(5) 0.6199(4) -0.0798(8) 0.0228(9) Uani 0.5 1 d . U P B 2
C24B C 0.5416(5) 0.6774(4) -0.2394(7) 0.0180(9) Uani 0.5 1 d . U P B 2
C25B C 0.5285(5) 0.6501(4) -0.1049(11) 0.0190(9) Uani 0.5 1 d . U P B 2
C26B C 0.5912(7) 0.6203(8) -0.0277(11) 0.0204(9) Uani 0.5 1 d . U P B 2
C27B C 0.5755(9) 0.5938(10) 0.1044(14) 0.0209(9) Uani 0.5 1 d . U P B 2
C28B C 0.5019(6) 0.5954(8) 0.1603(15) 0.0215(9) Uani 0.5 1 d . U P B 2
C29B C 0.4379(3) 0.6276(4) 0.0807(5) 0.0228(9) Uani 0.5 1 d G U P B 2
C30B C 0.4498(2) 0.6545(4) -0.0495(5) 0.0205(8) Uani 0.5 1 d G U P B 2
C31B C 0.3863(3) 0.6829(3) -0.1243(4) 0.0225(9) Uani 0.5 1 d G U P B 2
C34B C 0.3109(2) 0.6844(3) -0.0688(5) 0.0275(10) Uani 0.5 1 d G U P B 2
H34B H 0.2674 0.7038 -0.1199 0.033 Uiso 0.5 1 calc R U P B 2
C35B C 0.2990(2) 0.6575(3) 0.0615(5) 0.0276(10) Uani 0.5 1 d G U P B 2
H35B H 0.2475 0.6585 0.0994 0.033 Uiso 0.5 1 calc R U P B 2
C36B C 0.3625(3) 0.6291(3) 0.1362(4) 0.0283(9) Uani 0.5 1 d G U P B 2
C40B C 0.7048(4) 0.5368(5) 0.0976(8) 0.0261(9) Uani 0.5 1 d D U P B 2
H40C H 0.7506 0.5219 0.1543 0.031 Uiso 0.5 1 calc R U P B 2
H40D H 0.6854 0.4871 0.0532 0.031 Uiso 0.5 1 calc R U P B 2
C22B C 0.6807(4) 0.6492(4) -0.2123(8) 0.0211(9) Uani 0.5 1 d . U P B 2
H22B H 0.7325 0.6500 -0.2494 0.025 Uiso 0.5 1 calc R U P B 2
C23B C 0.6167(5) 0.6767(4) -0.2884(8) 0.0179(9) Uani 0.5 1 d . U P B 2
H23B H 0.6260 0.6955 -0.3769 0.021 Uiso 0.5 1 calc R U P B 2
C32B C 0.3977(5) 0.7112(4) -0.2559(8) 0.0198(10) Uani 0.5 1 d . U P B 2
H32B H 0.3545 0.7324 -0.3056 0.024 Uiso 0.5 1 calc R U P B 2
C33B C 0.4730(4) 0.7077(4) -0.3124(7) 0.0200(9) Uani 0.5 1 d . U P B 2
H33B H 0.4799 0.7257 -0.4019 0.024 Uiso 0.5 1 calc R U P B 2
C37B C 0.4199(5) 0.6113(5) 0.3485(8) 0.0311(10) Uani 0.5 1 d . U P B 2
H37C H 0.4089 0.5891 0.4386 0.037 Uiso 0.5 1 calc R U P B 2
H37D H 0.4338 0.6692 0.3585 0.037 Uiso 0.5 1 calc R U P B 2
C38B C 0.5557(5) 0.5607(5) 0.3740(8) 0.0297(10) Uani 0.5 1 d D U P B 2
H38C H 0.5428 0.5282 0.4544 0.036 Uiso 0.5 1 calc R U P B 2
H38D H 0.5732 0.6149 0.4038 0.036 Uiso 0.5 1 calc R U P B 2
C39B C 0.6209(5) 0.5201(5) 0.2962(8) 0.0276(10) Uani 0.5 1 d D U P B 2
H39C H 0.6677 0.5124 0.3546 0.033 Uiso 0.5 1 calc R U P B 2
H39D H 0.6031 0.4663 0.2651 0.033 Uiso 0.5 1 calc R U P B 2
O1 O 1.15075(14) 0.81772(14) 0.7730(3) 0.0257(5) Uani 1 1 d . . . . .
O2 O 0.76820(13) 0.87631(13) 1.0089(2) 0.0217(5) Uani 1 1 d . . . . .
N1 N 1.01187(16) 0.80890(16) 0.7372(3) 0.0197(6) Uani 1 1 d . . . . .
N2 N 0.85395(15) 0.83886(16) 0.8324(3) 0.0191(5) Uani 1 1 d . . . . .
C1 C 1.13971(18) 0.84998(18) 0.8994(3) 0.0210(6) Uani 1 1 d . . . . .
C2 C 1.20466(19) 0.86747(19) 0.9788(4) 0.0238(7) Uani 1 1 d . . . . .
H2 H 1.2566 0.8577 0.9462 0.029 Uiso 1 1 calc R U . . .
C3 C 1.19385(19) 0.89931(19) 1.1062(4) 0.0228(7) Uani 1 1 d . . . . .
H3 H 1.2388 0.9118 1.1593 0.027 Uiso 1 1 calc R U . . .
C4 C 1.11761(18) 0.91345(18) 1.1583(3) 0.0199(6) Uani 1 1 d . . . . .
C5 C 1.05149(18) 0.89449(17) 1.0763(3) 0.0161(6) Uani 1 1 d . . . . .
C6 C 1.06275(18) 0.86298(18) 0.9463(3) 0.0175(6) Uani 1 1 d . . . . .
C7 C 0.99633(18) 0.84186(17) 0.8646(3) 0.0170(6) Uani 1 1 d . . . . .
C8 C 0.92121(18) 0.85328(17) 0.9109(3) 0.0162(6) Uani 1 1 d . . . . .
C9 C 0.90874(18) 0.88385(17) 1.0428(3) 0.0157(6) Uani 1 1 d . . . . .
C10 C 0.97331(18) 0.90439(17) 1.1260(3) 0.0155(6) Uani 1 1 d . . . . .
C11 C 0.9600(2) 0.93455(17) 1.2571(3) 0.0186(6) Uani 1 1 d . . . . .
C12 C 1.0282(2) 0.95296(18) 1.3383(3) 0.0213(7) Uani 1 1 d . . . . .
H12 H 1.0207 0.9722 1.4270 0.026 Uiso 1 1 calc R U . . .
C13 C 1.1029(2) 0.94346(18) 1.2907(3) 0.0222(7) Uani 1 1 d . . . . .
H13 H 1.1464 0.9570 1.3465 0.027 Uiso 1 1 calc R U . . .
C14 C 0.88163(19) 0.94641(18) 1.2991(3) 0.0201(6) Uani 1 1 d . . . . .
H14 H 0.8718 0.9670 1.3863 0.024 Uiso 1 1 calc R U . . .
C15 C 0.81815(18) 0.92869(18) 1.2157(3) 0.0198(7) Uani 1 1 d . . . . .
H15 H 0.7656 0.9389 1.2448 0.024 Uiso 1 1 calc R U . . .
C16 C 0.83167(18) 0.89621(18) 1.0904(3) 0.0182(6) Uani 1 1 d . . . . .
C17 C 0.78713(18) 0.81446(18) 0.9141(3) 0.0216(6) Uani 1 1 d . . . . .
H17A H 0.7408 0.8040 0.8561 0.026 Uiso 1 1 calc R U . . .
H17B H 0.8001 0.7637 0.9620 0.026 Uiso 1 1 calc R U . . .
C18 C 0.8694(2) 0.7886(2) 0.7149(3) 0.0239(7) Uani 1 1 d . . . . .
H18A H 0.8242 0.7921 0.6521 0.029 Uiso 1 1 calc R U . . .
H18B H 0.8755 0.7314 0.7425 0.029 Uiso 1 1 calc R U . . .
C19 C 0.9445(2) 0.8175(2) 0.6459(3) 0.0252(7) Uani 1 1 d . . . . .
H19A H 0.9538 0.7850 0.5641 0.030 Uiso 1 1 calc R U . . .
H19B H 0.9386 0.8748 0.6193 0.030 Uiso 1 1 calc R U . . .
C20 C 1.0878(2) 0.8364(2) 0.6826(3) 0.0258(7) Uani 1 1 d . . . . .
H20A H 1.0975 0.8096 0.5955 0.031 Uiso 1 1 calc R U . . .
H20B H 1.0858 0.8955 0.6674 0.031 Uiso 1 1 calc R U . . .


_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
O3A C21A 1.371(10) . ?
O3A C40A 1.425(10) . ?
O4A C36A 1.372(7) . ?
O4A C37A 1.452(9) . ?
N3A C27A 1.419(18) . ?
N3A C40A 1.435(8) . ?
N3A C39A 1.468(8) . ?
N4A C28A 1.426(16) . ?
N4A C37A 1.432(10) . ?
N4A C38A 1.444(8) . ?
C22A C23A 1.353(12) . ?
C22A C21A 1.451(12) . ?
C22A H22A 0.9500 . ?
C23A C24A 1.388(12) . ?
C23A H23A 0.9500 . ?
C32A C33A 1.368(12) . ?
C32A C31A 1.403(9) . ?
C32A H32A 0.9500 . ?
C33A C24A 1.473(12) . ?
C33A H33A 0.9500 . ?
C37A H37A 0.9900 . ?
C37A H37B 0.9900 . ?
C38A C39A 1.522(10) . ?
C38A H38A 0.9900 . ?
C38A H38B 0.9900 . ?
C21A C26A 1.396(14) . ?
C24A C25A 1.409(13) . ?
C25A C30A 1.442(10) . ?
C25A C26A 1.410(12) . ?
C26A C27A 1.435(17) . ?
C27A C28A 1.348(16) . ?
C28A C29A 1.446(10) . ?
C29A C30A 1.3900 . ?
C29A C36A 1.3900 . ?
C30A C31A 1.3900 . ?
C31A C34A 1.3900 . ?
C34A C35A 1.3900 . ?
C34A H34A 0.9500 . ?
C35A C36A 1.3900 . ?
C35A H35A 0.9500 . ?
C39A H39A 0.9900 . ?
C39A H39B 0.9900 . ?
C40A H40A 0.9900 . ?
C40A H40B 0.9900 . ?
O3B C21B 1.353(9) . ?
O3B C40B 1.438(9) . ?
O4B C36B 1.367(7) . ?
O4B C37B 1.464(11) . ?
N3B C27B 1.420(18) . ?
N3B C40B 1.457(9) . ?
N3B C39B 1.460(8) . ?
N4B C28B 1.391(16) . ?
N4B C37B 1.441(10) . ?
N4B C38B 1.467(9) . ?
C21B C26B 1.414(14) . ?
C21B C22B 1.423(11) . ?
C24B C23B 1.362(10) . ?
C24B C25B 1.435(13) . ?
C24B C33B 1.458(9) . ?
C25B C26B 1.400(12) . ?
C25B C30B 1.443(9) . ?
C26B C27B 1.416(16) . ?
C27B C28B 1.364(16) . ?
C28B C29B 1.443(12) . ?
C29B C30B 1.3900 . ?
C29B C36B 1.3900 . ?
C30B C31B 1.3900 . ?
C31B C34B 1.3900 . ?
C31B C32B 1.408(9) . ?
C34B C35B 1.3900 . ?
C34B H34B 0.9500 . ?
C35B C36B 1.3900 . ?
C35B H35B 0.9500 . ?
C40B H40C 0.9900 . ?
C40B H40D 0.9900 . ?
C22B C23B 1.398(10) . ?
C22B H22B 0.9500 . ?
C23B H23B 0.9500 . ?
C32B C33B 1.393(10) . ?
C32B H32B 0.9500 . ?
C33B H33B 0.9500 . ?
C37B H37C 0.9900 . ?
C37B H37D 0.9900 . ?
C38B C39B 1.506(11) . ?
C38B H38C 0.9900 . ?
C38B H38D 0.9900 . ?
C39B H39C 0.9900 . ?
C39B H39D 0.9900 . ?
O1 C1 1.383(4) . ?
O1 C20 1.430(4) . ?
O2 C16 1.386(4) . ?
O2 C17 1.429(4) . ?
N1 C7 1.409(4) . ?
N1 C20 1.466(4) . ?
N1 C19 1.466(4) . ?
N2 C8 1.401(4) . ?
N2 C17 1.451(4) . ?
N2 C18 1.461(4) . ?
C1 C2 1.385(5) . ?
C1 C6 1.399(4) . ?
C2 C3 1.389(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.409(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.420(4) . ?
C4 C13 1.435(5) . ?
C5 C6 1.412(4) . ?
C5 C10 1.421(4) . ?
C6 C7 1.431(4) . ?
C7 C8 1.364(4) . ?
C8 C9 1.427(4) . ?
C9 C16 1.402(4) . ?
C9 C10 1.413(4) . ?
C10 C11 1.419(4) . ?
C11 C14 1.403(4) . ?
C11 C12 1.442(4) . ?
C12 C13 1.358(5) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.390(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.381(5) . ?
C15 H15 0.9500 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.521(5) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C21A O3A C40A 112.4(6) . . ?
C36A O4A C37A 113.2(5) . . ?
C27A N3A C40A 112.8(7) . . ?
C27A N3A C39A 111.4(7) . . ?
C40A N3A C39A 115.6(6) . . ?
C28A N4A C37A 111.1(7) . . ?
C28A N4A C38A 113.8(6) . . ?
C37A N4A C38A 116.6(6) . . ?
C23A C22A C21A 121.0(7) . . ?
C23A C22A H22A 119.5 . . ?
C21A C22A H22A 119.5 . . ?
C24A C23A C22A 122.7(7) . . ?
C24A C23A H23A 118.7 . . ?
C22A C23A H23A 118.7 . . ?
C33A C32A C31A 121.2(7) . . ?
C33A C32A H32A 119.4 . . ?
C31A C32A H32A 119.4 . . ?
C32A C33A C24A 120.1(7) . . ?
C32A C33A H33A 119.9 . . ?
C24A C33A H33A 119.9 . . ?
N4A C37A O4A 111.8(6) . . ?
N4A C37A H37A 109.3 . . ?
O4A C37A H37A 109.3 . . ?
N4A C37A H37B 109.3 . . ?
O4A C37A H37B 109.3 . . ?
H37A C37A H37B 107.9 . . ?
N4A C38A C39A 110.5(6) . . ?
N4A C38A H38A 109.5 . . ?
C39A C38A H38A 109.5 . . ?
N4A C38A H38B 109.5 . . ?
C39A C38A H38B 109.5 . . ?
H38A C38A H38B 108.1 . . ?
O3A C21A C26A 120.7(7) . . ?
O3A C21A C22A 121.6(7) . . ?
C26A C21A C22A 117.6(8) . . ?
C23A C24A C33A 124.7(7) . . ?
C23A C24A C25A 116.9(8) . . ?
C33A C24A C25A 118.4(8) . . ?
C30A C25A C26A 118.0(9) . . ?
C30A C25A C24A 119.4(7) . . ?
C26A C25A C24A 122.6(9) . . ?
C21A C26A C25A 119.2(9) . . ?
C21A C26A C27A 118.9(10) . . ?
C25A C26A C27A 121.8(12) . . ?
C28A C27A N3A 123.6(12) . . ?
C28A C27A C26A 119.3(15) . . ?
N3A C27A C26A 117.1(10) . . ?
C27A C28A N4A 121.8(10) . . ?
C27A C28A C29A 120.8(13) . . ?
N4A C28A C29A 117.4(9) . . ?
C30A C29A C36A 120.0 . . ?
C30A C29A C28A 120.5(7) . . ?
C36A C29A C28A 119.5(7) . . ?
C31A C30A C29A 120.0 . . ?
C31A C30A C25A 120.3(5) . . ?
C29A C30A C25A 119.6(5) . . ?
C30A C31A C34A 120.0 . . ?
C30A C31A C32A 120.4(5) . . ?
C34A C31A C32A 119.6(5) . . ?
C35A C34A C31A 120.0 . . ?
C35A C34A H34A 120.0 . . ?
C31A C34A H34A 120.0 . . ?
C36A C35A C34A 120.0 . . ?
C36A C35A H35A 120.0 . . ?
C34A C35A H35A 120.0 . . ?
O4A C36A C35A 119.4(4) . . ?
O4A C36A C29A 120.5(4) . . ?
C35A C36A C29A 120.0 . . ?
N3A C39A C38A 109.8(6) . . ?
N3A C39A H39A 109.7 . . ?
C38A C39A H39A 109.7 . . ?
N3A C39A H39B 109.7 . . ?
C38A C39A H39B 109.7 . . ?
H39A C39A H39B 108.2 . . ?
O3A C40A N3A 111.1(6) . . ?
O3A C40A H40A 109.4 . . ?
N3A C40A H40A 109.4 . . ?
O3A C40A H40B 109.4 . . ?
N3A C40A H40B 109.4 . . ?
H40A C40A H40B 108.0 . . ?
C21B O3B C40B 112.6(6) . . ?
C36B O4B C37B 112.2(5) . . ?
C27B N3B C40B 111.6(7) . . ?
C27B N3B C39B 112.6(8) . . ?
C40B N3B C39B 114.5(6) . . ?
C28B N4B C37B 112.2(7) . . ?
C28B N4B C38B 113.5(7) . . ?
C37B N4B C38B 115.2(7) . . ?
O3B C21B C26B 119.6(7) . . ?
O3B C21B C22B 122.3(7) . . ?
C26B C21B C22B 118.0(7) . . ?
C23B C24B C25B 118.5(7) . . ?
C23B C24B C33B 124.4(7) . . ?
C25B C24B C33B 117.0(7) . . ?
C26B C25B C24B 120.7(8) . . ?
C26B C25B C30B 120.3(10) . . ?
C24B C25B C30B 119.0(7) . . ?
C21B C26B C25B 120.2(10) . . ?
C21B C26B C27B 121.1(10) . . ?
C25B C26B C27B 118.7(12) . . ?
C28B C27B N3B 120.6(11) . . ?
C28B C27B C26B 123.1(15) . . ?
N3B C27B C26B 116.2(11) . . ?
C27B C28B C29B 117.8(13) . . ?
C27B C28B N4B 123.8(11) . . ?
C29B C28B N4B 118.4(8) . . ?
C30B C29B C36B 120.0 . . ?
C30B C29B C28B 121.7(6) . . ?
C36B C29B C28B 118.3(6) . . ?
C31B C30B C29B 120.0 . . ?
C31B C30B C25B 121.6(5) . . ?
C29B C30B C25B 118.4(5) . . ?
C30B C31B C34B 120.0 . . ?
C30B C31B C32B 120.5(5) . . ?
C34B C31B C32B 119.5(5) . . ?
C35B C34B C31B 120.0 . . ?
C35B C34B H34B 120.0 . . ?
C31B C34B H34B 120.0 . . ?
C34B C35B C36B 120.0 . . ?
C34B C35B H35B 120.0 . . ?
C36B C35B H35B 120.0 . . ?
O4B C36B C35B 118.9(4) . . ?
O4B C36B C29B 121.1(4) . . ?
C35B C36B C29B 120.0 . . ?
O3B C40B N3B 111.0(6) . . ?
O3B C40B H40C 109.4 . . ?
N3B C40B H40C 109.4 . . ?
O3B C40B H40D 109.4 . . ?
N3B C40B H40D 109.4 . . ?
H40C C40B H40D 108.0 . . ?
C21B C22B C23B 120.6(7) . . ?
C21B C22B H22B 119.7 . . ?
C23B C22B H22B 119.7 . . ?
C24B C23B C22B 121.9(7) . . ?
C24B C23B H23B 119.0 . . ?
C22B C23B H23B 119.0 . . ?
C33B C32B C31B 119.3(6) . . ?
C33B C32B H32B 120.3 . . ?
C31B C32B H32B 120.3 . . ?
C32B C33B C24B 122.5(6) . . ?
C32B C33B H33B 118.7 . . ?
C24B C33B H33B 118.7 . . ?
O4B C37B N4B 110.1(6) . . ?
O4B C37B H37C 109.6 . . ?
N4B C37B H37C 109.6 . . ?
O4B C37B H37D 109.6 . . ?
N4B C37B H37D 109.6 . . ?
H37C C37B H37D 108.1 . . ?
N4B C38B C39B 109.6(6) . . ?
N4B C38B H38C 109.8 . . ?
C39B C38B H38C 109.8 . . ?
N4B C38B H38D 109.8 . . ?
C39B C38B H38D 109.8 . . ?
H38C C38B H38D 108.2 . . ?
N3B C39B C38B 109.5(6) . . ?
N3B C39B H39C 109.8 . . ?
C38B C39B H39C 109.8 . . ?
N3B C39B H39D 109.8 . . ?
C38B C39B H39D 109.8 . . ?
H39C C39B H39D 108.2 . . ?
C1 O1 C20 113.1(2) . . ?
C16 O2 C17 112.7(2) . . ?
C7 N1 C20 112.3(3) . . ?
C7 N1 C19 112.3(3) . . ?
C20 N1 C19 114.7(3) . . ?
C8 N2 C17 111.3(3) . . ?
C8 N2 C18 113.6(3) . . ?
C17 N2 C18 115.7(3) . . ?
O1 C1 C2 119.8(3) . . ?
O1 C1 C6 119.4(3) . . ?
C2 C1 C6 120.9(3) . . ?
C1 C2 C3 120.0(3) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C4 121.5(3) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C5 118.0(3) . . ?
C3 C4 C13 123.9(3) . . ?
C5 C4 C13 118.1(3) . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 C10 119.3(3) . . ?
C4 C5 C10 120.3(3) . . ?
C1 C6 C5 119.3(3) . . ?
C1 C6 C7 120.0(3) . . ?
C5 C6 C7 120.6(3) . . ?
C8 C7 N1 122.2(3) . . ?
C8 C7 C6 120.2(3) . . ?
N1 C7 C6 117.6(3) . . ?
C7 C8 N2 122.8(3) . . ?
C7 C8 C9 119.9(3) . . ?
N2 C8 C9 117.2(3) . . ?
C16 C9 C10 118.9(3) . . ?
C16 C9 C8 120.1(3) . . ?
C10 C9 C8 120.9(3) . . ?
C9 C10 C11 120.3(3) . . ?
C9 C10 C5 119.0(3) . . ?
C11 C10 C5 120.7(3) . . ?
C14 C11 C10 118.4(3) . . ?
C14 C11 C12 123.8(3) . . ?
C10 C11 C12 117.8(3) . . ?
C13 C12 C11 121.5(3) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C12 C13 C4 121.6(3) . . ?
C12 C13 H13 119.2 . . ?
C4 C13 H13 119.2 . . ?
C15 C14 C11 121.3(3) . . ?
C15 C14 H14 119.3 . . ?
C11 C14 H14 119.3 . . ?
C16 C15 C14 119.8(3) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 O2 119.8(3) . . ?
C15 C16 C9 121.2(3) . . ?
O2 C16 C9 119.1(3) . . ?
O2 C17 N2 110.4(2) . . ?
O2 C17 H17A 109.6 . . ?
N2 C17 H17A 109.6 . . ?
O2 C17 H17B 109.6 . . ?
N2 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
N2 C18 C19 109.6(3) . . ?
N2 C18 H18A 109.8 . . ?
C19 C18 H18A 109.8 . . ?
N2 C18 H18B 109.8 . . ?
C19 C18 H18B 109.8 . . ?
H18A C18 H18B 108.2 . . ?
N1 C19 C18 109.6(3) . . ?
N1 C19 H19A 109.7 . . ?
C18 C19 H19A 109.7 . . ?
N1 C19 H19B 109.7 . . ?
C18 C19 H19B 109.7 . . ?
H19A C19 H19B 108.2 . . ?
O1 C20 N1 110.5(3) . . ?
O1 C20 H20A 109.6 . . ?
N1 C20 H20A 109.6 . . ?
O1 C20 H20B 109.6 . . ?
N1 C20 H20B 109.6 . . ?
H20A C20 H20B 108.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C21A C22A C23A C24A 1.4(11) . . . . ?
C31A C32A C33A C24A -2.4(11) . . . . ?
C28A N4A C37A O4A 57.6(9) . . . . ?
C38A N4A C37A O4A -169.7(6) . . . . ?
C36A O4A C37A N4A -54.0(8) . . . . ?
C28A N4A C38A C39A -43.8(9) . . . . ?
C37A N4A C38A C39A -175.3(6) . . . . ?
C40A O3A C21A C26A 28.2(10) . . . . ?
C40A O3A C21A C22A -154.3(7) . . . . ?
C23A C22A C21A O3A -178.2(7) . . . . ?
C23A C22A C21A C26A -0.6(11) . . . . ?
C22A C23A C24A C33A 177.9(7) . . . . ?
C22A C23A C24A C25A -0.2(10) . . . . ?
C32A C33A C24A C23A -177.5(7) . . . . ?
C32A C33A C24A C25A 0.6(10) . . . . ?
C23A C24A C25A C30A 177.9(6) . . . . ?
C33A C24A C25A C30A -0.4(8) . . . . ?
C23A C24A C25A C26A -1.7(9) . . . . ?
C33A C24A C25A C26A 180.0(8) . . . . ?
O3A C21A C26A C25A 176.3(8) . . . . ?
C22A C21A C26A C25A -1.3(13) . . . . ?
O3A C21A C26A C27A 0.4(15) . . . . ?
C22A C21A C26A C27A -177.2(11) . . . . ?
C30A C25A C26A C21A -177.1(8) . . . . ?
C24A C25A C26A C21A 2.5(13) . . . . ?
C30A C25A C26A C27A -1.3(15) . . . . ?
C24A C25A C26A C27A 178.3(10) . . . . ?
C40A N3A C27A C28A 153.9(12) . . . . ?
C39A N3A C27A C28A 22.0(17) . . . . ?
C40A N3A C27A C26A -27.5(15) . . . . ?
C39A N3A C27A C26A -159.4(11) . . . . ?
C21A C26A C27A C28A 178.0(12) . . . . ?
C25A C26A C27A C28A 2(2) . . . . ?
C21A C26A C27A N3A -0.7(19) . . . . ?
C25A C26A C27A N3A -176.5(10) . . . . ?
N3A C27A C28A N4A -5(2) . . . . ?
C26A C27A C28A N4A 176.8(12) . . . . ?
N3A C27A C28A C29A 176.9(11) . . . . ?
C26A C27A C28A C29A -2(2) . . . . ?
C37A N4A C28A C27A 150.5(12) . . . . ?
C38A N4A C28A C27A 16.4(15) . . . . ?
C37A N4A C28A C29A -31.0(12) . . . . ?
C38A N4A C28A C29A -165.2(8) . . . . ?
C27A C28A C29A C30A 0.5(15) . . . . ?
N4A C28A C29A C30A -178.1(6) . . . . ?
C27A C28A C29A C36A 179.3(10) . . . . ?
N4A C28A C29A C36A 0.8(12) . . . . ?
C36A C29A C30A C31A 0.0 . . . . ?
C28A C29A C30A C31A 178.8(8) . . . . ?
C36A C29A C30A C25A -178.4(6) . . . . ?
C28A C29A C30A C25A 0.4(7) . . . . ?
C26A C25A C30A C31A -178.4(7) . . . . ?
C24A C25A C30A C31A 2.0(7) . . . . ?
C26A C25A C30A C29A 0.0(8) . . . . ?
C24A C25A C30A C29A -179.6(4) . . . . ?
C29A C30A C31A C34A 0.0 . . . . ?
C25A C30A C31A C34A 178.4(6) . . . . ?
C29A C30A C31A C32A 177.8(5) . . . . ?
C25A C30A C31A C32A -3.7(6) . . . . ?
C33A C32A C31A C30A 4.0(9) . . . . ?
C33A C32A C31A C34A -178.2(6) . . . . ?
C30A C31A C34A C35A 0.0 . . . . ?
C32A C31A C34A C35A -177.9(5) . . . . ?
C31A C34A C35A C36A 0.0 . . . . ?
C37A O4A C36A C35A -154.9(5) . . . . ?
C37A O4A C36A C29A 22.6(7) . . . . ?
C34A C35A C36A O4A 177.5(5) . . . . ?
C34A C35A C36A C29A 0.0 . . . . ?
C30A C29A C36A O4A -177.5(5) . . . . ?
C28A C29A C36A O4A 3.7(8) . . . . ?
C30A C29A C36A C35A 0.0 . . . . ?
C28A C29A C36A C35A -178.8(8) . . . . ?
C27A N3A C39A C38A -48.7(9) . . . . ?
C40A N3A C39A C38A -179.2(6) . . . . ?
N4A C38A C39A N3A 61.5(7) . . . . ?
C21A O3A C40A N3A -56.5(8) . . . . ?
C27A N3A C40A O3A 56.3(10) . . . . ?
C39A N3A C40A O3A -173.8(6) . . . . ?
C40B O3B C21B C26B 27.4(10) . . . . ?
C40B O3B C21B C22B -154.5(6) . . . . ?
C23B C24B C25B C26B -2.6(9) . . . . ?
C33B C24B C25B C26B -179.8(8) . . . . ?
C23B C24B C25B C30B 176.8(6) . . . . ?
C33B C24B C25B C30B -0.4(7) . . . . ?
O3B C21B C26B C25B 177.2(8) . . . . ?
C22B C21B C26B C25B -1.0(13) . . . . ?
O3B C21B C26B C27B -0.4(16) . . . . ?
C22B C21B C26B C27B -178.6(11) . . . . ?
C24B C25B C26B C21B 2.6(13) . . . . ?
C30B C25B C26B C21B -176.8(8) . . . . ?
C24B C25B C26B C27B -179.8(10) . . . . ?
C30B C25B C26B C27B 0.8(15) . . . . ?
C40B N3B C27B C28B 153.6(12) . . . . ?
C39B N3B C27B C28B 23.1(16) . . . . ?
C40B N3B C27B C26B -30.8(15) . . . . ?
C39B N3B C27B C26B -161.3(11) . . . . ?
C21B C26B C27B C28B 177.9(12) . . . . ?
C25B C26B C27B C28B 0(2) . . . . ?
C21B C26B C27B N3B 2.4(19) . . . . ?
C25B C26B C27B N3B -175.1(10) . . . . ?
N3B C27B C28B C29B 173.9(11) . . . . ?
C26B C27B C28B C29B -1(2) . . . . ?
N3B C27B C28B N4B -6(2) . . . . ?
C26B C27B C28B N4B 178.9(13) . . . . ?
C37B N4B C28B C27B 150.2(12) . . . . ?
C38B N4B C28B C27B 17.4(15) . . . . ?
C37B N4B C28B C29B -29.5(13) . . . . ?
C38B N4B C28B C29B -162.3(9) . . . . ?
C27B C28B C29B C30B 1.4(14) . . . . ?
N4B C28B C29B C30B -178.9(7) . . . . ?
C27B C28B C29B C36B 179.6(10) . . . . ?
N4B C28B C29B C36B -0.7(13) . . . . ?
C36B C29B C30B C31B 0.0 . . . . ?
C28B C29B C30B C31B 178.2(8) . . . . ?
C36B C29B C30B C25B -178.5(6) . . . . ?
C28B C29B C30B C25B -0.3(7) . . . . ?
C26B C25B C30B C31B -179.2(7) . . . . ?
C24B C25B C30B C31B 1.3(7) . . . . ?
C26B C25B C30B C29B -0.8(8) . . . . ?
C24B C25B C30B C29B 179.8(3) . . . . ?
C29B C30B C31B C34B 0.0 . . . . ?
C25B C30B C31B C34B 178.4(6) . . . . ?
C29B C30B C31B C32B 179.3(5) . . . . ?
C25B C30B C31B C32B -2.3(6) . . . . ?
C30B C31B C34B C35B 0.0 . . . . ?
C32B C31B C34B C35B -179.3(5) . . . . ?
C31B C34B C35B C36B 0.0 . . . . ?
C37B O4B C36B C35B -153.4(5) . . . . ?
C37B O4B C36B C29B 26.1(7) . . . . ?
C34B C35B C36B O4B 179.6(5) . . . . ?
C34B C35B C36B C29B 0.0 . . . . ?
C30B C29B C36B O4B -179.5(5) . . . . ?
C28B C29B C36B O4B 2.2(8) . . . . ?
C30B C29B C36B C35B 0.0 . . . . ?
C28B C29B C36B C35B -178.2(8) . . . . ?
C21B O3B C40B N3B -56.4(8) . . . . ?
C27B N3B C40B O3B 58.2(10) . . . . ?
C39B N3B C40B O3B -172.3(6) . . . . ?
O3B C21B C22B C23B -178.7(6) . . . . ?
C26B C21B C22B C23B -0.6(10) . . . . ?
C25B C24B C23B C22B 1.0(9) . . . . ?
C33B C24B C23B C22B 178.0(6) . . . . ?
C21B C22B C23B C24B 0.6(10) . . . . ?
C30B C31B C32B C33B 2.3(8) . . . . ?
C34B C31B C32B C33B -178.4(5) . . . . ?
C31B C32B C33B C24B -1.4(10) . . . . ?
C23B C24B C33B C32B -176.6(6) . . . . ?
C25B C24B C33B C32B 0.5(8) . . . . ?
C36B O4B C37B N4B -55.8(8) . . . . ?
C28B N4B C37B O4B 57.5(9) . . . . ?
C38B N4B C37B O4B -170.6(6) . . . . ?
C28B N4B C38B C39B -44.6(9) . . . . ?
C37B N4B C38B C39B -175.9(6) . . . . ?
C27B N3B C39B C38B -50.6(10) . . . . ?
C40B N3B C39B C38B -179.6(6) . . . . ?
N4B C38B C39B N3B 62.2(8) . . . . ?
C20 O1 C1 C2 -153.1(3) . . . . ?
C20 O1 C1 C6 28.2(4) . . . . ?
O1 C1 C2 C3 -179.5(3) . . . . ?
C6 C1 C2 C3 -0.8(5) . . . . ?
C1 C2 C3 C4 0.9(5) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C2 C3 C4 C13 177.7(3) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C13 C4 C5 C6 -178.5(3) . . . . ?
C3 C4 C5 C10 177.4(3) . . . . ?
C13 C4 C5 C10 -0.7(4) . . . . ?
O1 C1 C6 C5 178.8(3) . . . . ?
C2 C1 C6 C5 0.1(4) . . . . ?
O1 C1 C6 C7 0.9(4) . . . . ?
C2 C1 C6 C7 -177.8(3) . . . . ?
C4 C5 C6 C1 0.5(4) . . . . ?
C10 C5 C6 C1 -177.3(3) . . . . ?
C4 C5 C6 C7 178.4(3) . . . . ?
C10 C5 C6 C7 0.6(4) . . . . ?
C20 N1 C7 C8 152.6(3) . . . . ?
C19 N1 C7 C8 21.5(4) . . . . ?
C20 N1 C7 C6 -27.8(4) . . . . ?
C19 N1 C7 C6 -158.9(3) . . . . ?
C1 C6 C7 C8 179.0(3) . . . . ?
C5 C6 C7 C8 1.1(4) . . . . ?
C1 C6 C7 N1 -0.6(4) . . . . ?
C5 C6 C7 N1 -178.5(3) . . . . ?
N1 C7 C8 N2 -4.8(4) . . . . ?
C6 C7 C8 N2 175.6(3) . . . . ?
N1 C7 C8 C9 177.5(3) . . . . ?
C6 C7 C8 C9 -2.1(4) . . . . ?
C17 N2 C8 C7 150.2(3) . . . . ?
C18 N2 C8 C7 17.5(4) . . . . ?
C17 N2 C8 C9 -32.0(4) . . . . ?
C18 N2 C8 C9 -164.7(3) . . . . ?
C7 C8 C9 C16 179.6(3) . . . . ?
N2 C8 C9 C16 1.7(4) . . . . ?
C7 C8 C9 C10 1.5(4) . . . . ?
N2 C8 C9 C10 -176.4(3) . . . . ?
C16 C9 C10 C11 2.0(4) . . . . ?
C8 C9 C10 C11 -179.9(3) . . . . ?
C16 C9 C10 C5 -177.9(3) . . . . ?
C8 C9 C10 C5 0.2(4) . . . . ?
C6 C5 C10 C9 -1.2(4) . . . . ?
C4 C5 C10 C9 -179.0(3) . . . . ?
C6 C5 C10 C11 178.9(3) . . . . ?
C4 C5 C10 C11 1.0(4) . . . . ?
C9 C10 C11 C14 -2.6(4) . . . . ?
C5 C10 C11 C14 177.3(3) . . . . ?
C9 C10 C11 C12 178.8(3) . . . . ?
C5 C10 C11 C12 -1.3(4) . . . . ?
C14 C11 C12 C13 -177.3(3) . . . . ?
C10 C11 C12 C13 1.3(4) . . . . ?
C11 C12 C13 C4 -1.0(5) . . . . ?
C3 C4 C13 C12 -177.3(3) . . . . ?
C5 C4 C13 C12 0.7(4) . . . . ?
C10 C11 C14 C15 0.5(4) . . . . ?
C12 C11 C14 C15 179.0(3) . . . . ?
C11 C14 C15 C16 2.2(5) . . . . ?
C14 C15 C16 O2 178.1(3) . . . . ?
C14 C15 C16 C9 -2.8(4) . . . . ?
C17 O2 C16 C15 -154.7(3) . . . . ?
C17 O2 C16 C9 26.2(4) . . . . ?
C10 C9 C16 C15 0.7(4) . . . . ?
C8 C9 C16 C15 -177.4(3) . . . . ?
C10 C9 C16 O2 179.8(2) . . . . ?
C8 C9 C16 O2 1.7(4) . . . . ?
C16 O2 C17 N2 -56.9(3) . . . . ?
C8 N2 C17 O2 59.9(3) . . . . ?
C18 N2 C17 O2 -168.3(2) . . . . ?
C8 N2 C18 C19 -44.9(3) . . . . ?
C17 N2 C18 C19 -175.6(3) . . . . ?
C7 N1 C19 C18 -49.0(3) . . . . ?
C20 N1 C19 C18 -178.8(3) . . . . ?
N2 C18 C19 N1 61.8(3) . . . . ?
C1 O1 C20 N1 -56.5(3) . . . . ?
C7 N1 C20 O1 56.3(3) . . . . ?
C19 N1 C20 O1 -173.8(2) . . . . ?

_refine_diff_density_max         0.447
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.062

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1502359'
_audit_update_record             
;
2016-09-02 deposited with the CCDC.
2018-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H6 N O'
_chemical_formula_sum            'C9 H6 N O'
_chemical_formula_weight         144.15

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   13.3145(4)
_cell_length_b                   13.4792(4)
_cell_length_c                   7.0709(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.9420(10)
_cell_angle_gamma                90
_cell_volume                     1266.00(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3289
_cell_measurement_theta_min      6.568
_cell_measurement_theta_max      74.530

_exptl_crystal_description       'thin plate'
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.174
_exptl_crystal_size_min          0.101
_exptl_absorpt_coefficient_mu    0.815
_shelx_estimated_absorpt_T_min   0.825
_shelx_estimated_absorpt_T_max   0.922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.825
_exptl_absorpt_correction_T_max  0.922
_exptl_absorpt_process_details   Sadabs
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker AXS D8 Venture '
_diffrn_measurement_method       'profile data from θ/2θ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6746
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         6.568
_diffrn_reflns_theta_max         74.530
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1293
_reflns_number_gt                1170
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX v2014.11.0'
_computing_cell_refinement       
'SHELXTL, Acta Cryst., Sect. A 2008, 64, 112-122.'
_computing_data_reduction        'Saint, APEX v2014.11.0.'
_computing_structure_solution    'SHELXT, Acta Cryst., Sect. A 2015, A71, 3-8.'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  'APEX v2014.11.0.'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0718P)²+0.4279P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1293
_refine_ls_number_parameters     104
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.1143
_refine_ls_wR_factor_gt          0.1095
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.40261(6) 0.25271(6) 0.67574(11) 0.0173(2) Uani 1 1 d . . . . .
O1 O 0.23872(5) 0.35378(5) 0.59045(10) 0.0207(2) Uani 1 1 d . . . . .
C1 C 0.45915(6) 0.16060(7) 0.67003(12) 0.0177(3) Uani 1 1 d . . . . .
H1A H 0.4897 0.1545 0.5468 0.021 Uiso 1 1 calc R U . . .
H1B H 0.4136 0.1034 0.6838 0.021 Uiso 1 1 calc R U . . .
C2 C 0.44689(7) 0.34036(7) 0.71346(13) 0.0145(3) Uani 1 1 d . . . . .
C3 C 0.39557(7) 0.43091(7) 0.68617(12) 0.0148(3) Uani 1 1 d . . . . .
C4 C 0.28903(7) 0.43160(7) 0.62080(13) 0.0166(3) Uani 1 1 d . . . . .
C5 C 0.24171(7) 0.52804(8) 0.59275(13) 0.0191(3) Uani 1 1 d . . . . .
H5 H 0.1729 0.5310 0.5479 0.023 Uiso 1 1 calc R U . . .
C6 C 0.29218(7) 0.61339(7) 0.62826(13) 0.0188(3) Uani 1 1 d . . . . .
H6 H 0.2576 0.6747 0.6109 0.023 Uiso 1 1 calc R U . . .
C7 C 0.39742(7) 0.61407(7) 0.69188(13) 0.0167(3) Uani 1 1 d . . . . .
C8 C 0.44771(7) 0.52240(7) 0.71981(13) 0.0145(3) Uani 1 1 d . . . . .
C9 C 0.44903(7) 0.70391(7) 0.72250(13) 0.0193(3) Uani 1 1 d . . . . .
H9 H 0.4140 0.7650 0.7055 0.023 Uiso 1 1 calc R U . . .
H1 H 0.3385(12) 0.2578(11) 0.617(2) 0.049(4) Uiso 1 1 d . U . . .


_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
N1 C2 1.3391(12) . ?
N1 C1 1.4541(11) . ?
N1 H1 0.926(15) . ?
O1 C4 1.2552(12) . ?
C1 C1 1.5143(16) 2_656 ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.4056(12) . ?
C2 C2 1.4719(17) 2_656 ?
C3 C8 1.4272(13) . ?
C3 C4 1.4614(14) . ?
C4 C5 1.4523(13) . ?
C5 C6 1.3472(14) . ?
C5 H5 0.9500 . ?
C6 C7 1.4420(14) . ?
C6 H6 0.9500 . ?
C7 C9 1.4018(13) . ?
C7 C8 1.4127(13) . ?
C8 C8 1.4281(18) 2_656 ?
C9 C9 1.3859(19) 2_656 ?
C9 H9 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 122.49(8) . . ?
C2 N1 H1 113.8(9) . . ?
C1 N1 H1 120.9(9) . . ?
N1 C1 C1 109.03(6) . 2_656 ?
N1 C1 H1A 109.9 . . ?
C1 C1 H1A 109.9 2_656 . ?
N1 C1 H1B 109.9 . . ?
C1 C1 H1B 109.9 2_656 . ?
H1A C1 H1B 108.3 . . ?
N1 C2 C3 122.38(9) . . ?
N1 C2 C2 117.99(5) . 2_656 ?
C3 C2 C2 119.63(6) . 2_656 ?
C2 C3 C8 120.08(10) . . ?
C2 C3 C4 120.07(8) . . ?
C8 C3 C4 119.84(8) . . ?
O1 C4 C5 120.22(9) . . ?
O1 C4 C3 122.94(8) . . ?
C5 C4 C3 116.84(8) . . ?
C6 C5 C4 122.19(9) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C5 C6 C7 121.68(9) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C9 C7 C8 120.76(10) . . ?
C9 C7 C6 120.61(9) . . ?
C8 C7 C6 118.63(9) . . ?
C7 C8 C3 120.80(10) . . ?
C7 C8 C8 119.00(6) . 2_656 ?
C3 C8 C8 120.19(6) . 2_656 ?
C9 C9 C7 120.23(6) 2_656 . ?
C9 C9 H9 119.9 2_656 . ?
C7 C9 H9 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 C1 40.35(13) . . . 2_656 ?
C1 N1 C2 C3 168.39(8) . . . . ?
C1 N1 C2 C2 -11.80(15) . . . 2_656 ?
N1 C2 C3 C8 -176.93(8) . . . . ?
C2 C2 C3 C8 3.26(17) 2_656 . . . ?
N1 C2 C3 C4 2.23(16) . . . . ?
C2 C2 C3 C4 -177.58(9) 2_656 . . . ?
C2 C3 C4 O1 1.55(16) . . . . ?
C8 C3 C4 O1 -179.29(8) . . . . ?
C2 C3 C4 C5 -178.94(7) . . . . ?
C8 C3 C4 C5 0.22(15) . . . . ?
O1 C4 C5 C6 178.27(8) . . . . ?
C3 C4 C5 C6 -1.25(15) . . . . ?
C4 C5 C6 C7 1.63(16) . . . . ?
C5 C6 C7 C9 178.10(8) . . . . ?
C5 C6 C7 C8 -0.93(16) . . . . ?
C9 C7 C8 C3 -179.13(8) . . . . ?
C6 C7 C8 C3 -0.11(15) . . . . ?
C9 C7 C8 C8 0.09(17) . . . 2_656 ?
C6 C7 C8 C8 179.11(9) . . . 2_656 ?
C2 C3 C8 C7 179.58(8) . . . . ?
C4 C3 C8 C7 0.42(16) . . . . ?
C2 C3 C8 C8 0.37(17) . . . 2_656 ?
C4 C3 C8 C8 -178.79(9) . . . 2_656 ?
C8 C7 C9 C9 1.18(18) . . . 2_656 ?
C6 C7 C9 C9 -177.82(10) . . . 2_656 ?

_refine_diff_density_max         0.318
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.058

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_g211
_database_code_depnum_ccdc_archive 'CCDC 1502356'
_audit_update_record             
;
2016-09-02 deposited with the CCDC.
2018-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 N2 O2'
_chemical_formula_weight         316.35

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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

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

_cell_length_a                   17.230(3)
_cell_length_b                   8.7235(16)
_cell_length_c                   9.6499(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1450.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2903
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      28.12

_exptl_crystal_description       Plate
_exptl_crystal_colour            Pale_yellow
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.945
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6351
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10504
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.335
_diffrn_reflns_theta_max         28.266
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             3546
_reflns_number_gt                3262
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.855
_reflns_Friedel_fraction_max     0.962
_reflns_Friedel_fraction_full    0.958

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0602P)²+0.3017P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1277 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.1(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3546
_refine_ls_number_parameters     222
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1155
_refine_ls_wR_factor_gt          0.1125
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.36338(11) 0.1311(2) 0.2665(2) 0.0255(5) Uani 1 1 d . . . . .
O2 O 0.72153(11) 0.4216(2) 0.5053(2) 0.0227(4) Uani 1 1 d . . . . .
H2 H 0.708(2) 0.384(5) 0.410(5) 0.052(12) Uiso 1 1 d . . . . .
N1 N 0.49630(13) 0.1777(3) 0.2226(2) 0.0187(5) Uani 1 1 d . . . . .
N2 N 0.64920(12) 0.2589(3) 0.3170(2) 0.0170(5) Uani 1 1 d . . . . .
C1 C 0.62467(16) 0.2698(3) 0.1705(3) 0.0212(6) Uani 1 1 d . . . . .
H1A H 0.6704 0.2552 0.1099 0.025 Uiso 1 1 calc R U . . .
H1B H 0.6036 0.3735 0.1528 0.025 Uiso 1 1 calc R U . . .
C2 C 0.56373(16) 0.1514(3) 0.1347(3) 0.0212(6) Uani 1 1 d . . . . .
H2A H 0.5489 0.1606 0.0359 0.025 Uiso 1 1 calc R U . . .
H2B H 0.5844 0.0470 0.1505 0.025 Uiso 1 1 calc R U . . .
C3 C 0.43305(16) 0.0708(3) 0.2078(3) 0.0232(6) Uani 1 1 d . . . . .
H3A H 0.4246 0.0489 0.1082 0.028 Uiso 1 1 calc R U . . .
H3B H 0.4465 -0.0267 0.2545 0.028 Uiso 1 1 calc R U . . .
C4 C 0.37247(15) 0.1775(3) 0.4018(3) 0.0200(6) Uani 1 1 d . . . . .
C5 C 0.30791(15) 0.1855(3) 0.4873(3) 0.0246(6) Uani 1 1 d . . . . .
H5 H 0.2582 0.1583 0.4523 0.030 Uiso 1 1 calc R U . . .
C6 C 0.31563(15) 0.2327(3) 0.6228(3) 0.0242(6) Uani 1 1 d . . . . .
H6 H 0.2709 0.2374 0.6801 0.029 Uiso 1 1 calc R U . . .
C7 C 0.38800(15) 0.2741(3) 0.6784(3) 0.0195(6) Uani 1 1 d . . . . .
C8 C 0.45393(15) 0.2693(3) 0.5902(3) 0.0150(5) Uani 1 1 d . . . . .
C9 C 0.44551(14) 0.2200(3) 0.4511(3) 0.0156(5) Uani 1 1 d . . . . .
C10 C 0.51131(15) 0.2188(3) 0.3603(3) 0.0151(5) Uani 1 1 d . . . . .
C11 C 0.58264(14) 0.2629(3) 0.4076(3) 0.0133(5) Uani 1 1 d . . . . .
C12 C 0.59167(14) 0.3229(3) 0.5457(3) 0.0141(5) Uani 1 1 d . . . . .
C13 C 0.52774(14) 0.3199(3) 0.6385(3) 0.0141(5) Uani 1 1 d . . . . .
C14 C 0.53528(15) 0.3722(3) 0.7769(3) 0.0166(5) Uani 1 1 d . . . . .
C15 C 0.46895(16) 0.3674(3) 0.8666(3) 0.0220(6) Uani 1 1 d . . . . .
H15 H 0.4744 0.3967 0.9609 0.026 Uiso 1 1 calc R U . . .
C16 C 0.39866(16) 0.3217(3) 0.8191(3) 0.0232(6) Uani 1 1 d . . . . .
H16 H 0.3555 0.3212 0.8805 0.028 Uiso 1 1 calc R U . . .
C17 C 0.60708(16) 0.4318(3) 0.8196(3) 0.0194(5) Uani 1 1 d . . . . .
H17 H 0.6140 0.4627 0.9132 0.023 Uiso 1 1 calc R U . . .
C18 C 0.66759(15) 0.4458(3) 0.7273(3) 0.0189(5) Uani 1 1 d . . . . .
H18 H 0.7149 0.4910 0.7570 0.023 Uiso 1 1 calc R U . . .
C19 C 0.66062(14) 0.3947(3) 0.5910(3) 0.0164(5) Uani 1 1 d . . . . .
C20 C 0.69823(16) 0.1233(3) 0.3437(3) 0.0244(6) Uani 1 1 d . . . . .
H20A H 0.7133 0.1213 0.4416 0.037 Uiso 1 1 calc R U . . .
H20B H 0.7449 0.1284 0.2859 0.037 Uiso 1 1 calc R U . . .
H20C H 0.6691 0.0300 0.3213 0.037 Uiso 1 1 calc R U . . .


_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 C4 1.376(3) . ?
O1 C3 1.428(3) . ?
O2 C19 1.357(3) . ?
O2 H2 1.01(5) . ?
N1 C10 1.400(3) . ?
N1 C3 1.441(3) . ?
N1 C2 1.457(3) . ?
N2 C11 1.442(3) . ?
N2 C20 1.477(3) . ?
N2 C1 1.478(3) . ?
C1 C2 1.513(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.386(4) . ?
C4 C9 1.395(3) . ?
C5 C6 1.378(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.405(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.420(4) . ?
C7 C16 1.432(4) . ?
C8 C9 1.418(4) . ?
C8 C13 1.424(4) . ?
C9 C10 1.433(4) . ?
C10 C11 1.366(3) . ?
C11 C12 1.440(3) . ?
C12 C19 1.412(3) . ?
C12 C13 1.420(3) . ?
C13 C14 1.418(4) . ?
C14 C17 1.404(4) . ?
C14 C15 1.435(4) . ?
C15 C16 1.355(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.377(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.394(4) . ?
C18 H18 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O1 C3 112.9(2) . . ?
C19 O2 H2 109(2) . . ?
C10 N1 C3 113.6(2) . . ?
C10 N1 C2 116.5(2) . . ?
C3 N1 C2 116.3(2) . . ?
C11 N2 C20 111.6(2) . . ?
C11 N2 C1 110.5(2) . . ?
C20 N2 C1 112.4(2) . . ?
N2 C1 C2 111.9(2) . . ?
N2 C1 H1A 109.2 . . ?
C2 C1 H1A 109.2 . . ?
N2 C1 H1B 109.2 . . ?
C2 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
N1 C2 C1 108.2(2) . . ?
N1 C2 H2A 110.0 . . ?
C1 C2 H2A 110.1 . . ?
N1 C2 H2B 110.0 . . ?
C1 C2 H2B 110.1 . . ?
H2A C2 H2B 108.4 . . ?
O1 C3 N1 111.0(2) . . ?
O1 C3 H3A 109.4 . . ?
N1 C3 H3A 109.4 . . ?
O1 C3 H3B 109.4 . . ?
N1 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
O1 C4 C5 119.2(2) . . ?
O1 C4 C9 120.3(3) . . ?
C5 C4 C9 120.5(3) . . ?
C6 C5 C4 120.1(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 121.7(3) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C6 C7 C8 118.3(3) . . ?
C6 C7 C16 123.4(2) . . ?
C8 C7 C16 118.3(2) . . ?
C9 C8 C7 119.6(2) . . ?
C9 C8 C13 119.7(2) . . ?
C7 C8 C13 120.6(2) . . ?
C4 C9 C8 119.7(2) . . ?
C4 C9 C10 120.3(3) . . ?
C8 C9 C10 120.0(2) . . ?
C11 C10 N1 123.7(2) . . ?
C11 C10 C9 120.4(2) . . ?
N1 C10 C9 115.8(2) . . ?
C10 C11 C12 120.6(2) . . ?
C10 C11 N2 120.4(2) . . ?
C12 C11 N2 118.9(2) . . ?
C19 C12 C13 117.7(2) . . ?
C19 C12 C11 122.6(2) . . ?
C13 C12 C11 119.6(2) . . ?
C14 C13 C12 121.1(2) . . ?
C14 C13 C8 119.3(2) . . ?
C12 C13 C8 119.5(2) . . ?
C17 C14 C13 118.5(2) . . ?
C17 C14 C15 122.4(2) . . ?
C13 C14 C15 119.1(2) . . ?
C16 C15 C14 121.1(3) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C15 C16 C7 121.4(2) . . ?
C15 C16 H16 119.3 . . ?
C7 C16 H16 119.3 . . ?
C18 C17 C14 120.7(2) . . ?
C18 C17 H17 119.7 . . ?
C14 C17 H17 119.7 . . ?
C17 C18 C19 121.1(2) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
O2 C19 C18 116.9(2) . . ?
O2 C19 C12 122.6(2) . . ?
C18 C19 C12 120.4(2) . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 N2 C1 C2 -52.6(3) . . . . ?
C20 N2 C1 C2 72.9(3) . . . . ?
C10 N1 C2 C1 -39.1(3) . . . . ?
C3 N1 C2 C1 -177.3(2) . . . . ?
N2 C1 C2 N1 60.4(3) . . . . ?
C4 O1 C3 N1 -53.6(3) . . . . ?
C10 N1 C3 O1 57.6(3) . . . . ?
C2 N1 C3 O1 -163.1(2) . . . . ?
C3 O1 C4 C5 -156.8(2) . . . . ?
C3 O1 C4 C9 24.9(3) . . . . ?
O1 C4 C5 C6 -179.5(2) . . . . ?
C9 C4 C5 C6 -1.3(4) . . . . ?
C4 C5 C6 C7 0.1(4) . . . . ?
C5 C6 C7 C8 1.3(4) . . . . ?
C5 C6 C7 C16 -179.1(3) . . . . ?
C6 C7 C8 C9 -1.5(3) . . . . ?
C16 C7 C8 C9 178.9(2) . . . . ?
C6 C7 C8 C13 175.7(2) . . . . ?
C16 C7 C8 C13 -3.9(3) . . . . ?
O1 C4 C9 C8 179.2(2) . . . . ?
C5 C4 C9 C8 1.0(4) . . . . ?
O1 C4 C9 C10 1.4(4) . . . . ?
C5 C4 C9 C10 -176.9(2) . . . . ?
C7 C8 C9 C4 0.4(3) . . . . ?
C13 C8 C9 C4 -176.9(2) . . . . ?
C7 C8 C9 C10 178.3(2) . . . . ?
C13 C8 C9 C10 1.0(3) . . . . ?
C3 N1 C10 C11 152.1(2) . . . . ?
C2 N1 C10 C11 12.9(4) . . . . ?
C3 N1 C10 C9 -31.0(3) . . . . ?
C2 N1 C10 C9 -170.2(2) . . . . ?
C4 C9 C10 C11 178.8(2) . . . . ?
C8 C9 C10 C11 1.0(3) . . . . ?
C4 C9 C10 N1 1.8(3) . . . . ?
C8 C9 C10 N1 -176.1(2) . . . . ?
N1 C10 C11 C12 171.8(2) . . . . ?
C9 C10 C11 C12 -5.0(4) . . . . ?
N1 C10 C11 N2 -4.4(4) . . . . ?
C9 C10 C11 N2 178.8(2) . . . . ?
C20 N2 C11 C10 -101.5(3) . . . . ?
C1 N2 C11 C10 24.4(3) . . . . ?
C20 N2 C11 C12 82.2(3) . . . . ?
C1 N2 C11 C12 -151.9(2) . . . . ?
C10 C11 C12 C19 -168.5(2) . . . . ?
N2 C11 C12 C19 7.7(3) . . . . ?
C10 C11 C12 C13 7.1(3) . . . . ?
N2 C11 C12 C13 -176.6(2) . . . . ?
C19 C12 C13 C14 -6.6(3) . . . . ?
C11 C12 C13 C14 177.5(2) . . . . ?
C19 C12 C13 C8 170.8(2) . . . . ?
C11 C12 C13 C8 -5.1(3) . . . . ?
C9 C8 C13 C14 178.6(2) . . . . ?
C7 C8 C13 C14 1.3(3) . . . . ?
C9 C8 C13 C12 1.1(3) . . . . ?
C7 C8 C13 C12 -176.1(2) . . . . ?
C12 C13 C14 C17 1.9(3) . . . . ?
C8 C13 C14 C17 -175.6(2) . . . . ?
C12 C13 C14 C15 179.8(2) . . . . ?
C8 C13 C14 C15 2.4(3) . . . . ?
C17 C14 C15 C16 174.2(3) . . . . ?
C13 C14 C15 C16 -3.6(4) . . . . ?
C14 C15 C16 C7 1.1(4) . . . . ?
C6 C7 C16 C15 -176.9(3) . . . . ?
C8 C7 C16 C15 2.7(4) . . . . ?
C13 C14 C17 C18 3.1(4) . . . . ?
C15 C14 C17 C18 -174.8(2) . . . . ?
C14 C17 C18 C19 -3.1(4) . . . . ?
C17 C18 C19 O2 176.1(2) . . . . ?
C17 C18 C19 C12 -1.9(4) . . . . ?
C13 C12 C19 O2 -171.3(2) . . . . ?
C11 C12 C19 O2 4.5(4) . . . . ?
C13 C12 C19 C18 6.7(4) . . . . ?
C11 C12 C19 C18 -177.6(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 N2 1.01(5) 1.74(4) 2.621(3) 144(4) .

_refine_diff_density_max         0.351
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.055



####################################################################### 
# 
# 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_G236
_database_code_depnum_ccdc_archive 'CCDC 1502358'
_audit_update_record             
;
2016-09-02 deposited with the CCDC.
2018-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H20 N2 O2'
_chemical_formula_weight         368.42

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   8.0334(12)
_cell_length_b                   24.561(4)
_cell_length_c                   9.1052(13)
_cell_angle_alpha                90
_cell_angle_beta                 105.603(2)
_cell_angle_gamma                90
_cell_volume                     1730.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2750
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      30.01

_exptl_crystal_description       Rod
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.948
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6412
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13154
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.658
_diffrn_reflns_theta_max         28.281
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4292
_reflns_number_gt                3349
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0819P)²+0.0778P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4292
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_ref         0.1443
_refine_ls_wR_factor_gt          0.1345
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.40695(11) 0.44708(4) 0.90722(10) 0.0193(2) Uani 1 1 d . . . . .
O2 O 0.12316(11) 0.47073(4) 0.12045(10) 0.0201(2) Uani 1 1 d . . . . .
N1 N 0.31899(13) 0.50405(4) 0.68940(11) 0.0147(2) Uani 1 1 d . . . . .
N2 N 0.18691(12) 0.51380(4) 0.36300(11) 0.0146(2) Uani 1 1 d . . . . .
C1 C 0.25380(15) 0.56177(5) 0.45874(14) 0.0151(3) Uani 1 1 d . . . . .
H1 H 0.3798 0.5659 0.4671 0.018 Uiso 1 1 calc R U . . .
C2 C 0.15923(17) 0.61346(5) 0.38804(16) 0.0207(3) Uani 1 1 d . . . . .
H2A H 0.1767 0.6190 0.2855 0.025 Uiso 1 1 calc R U . . .
H2B H 0.0338 0.6090 0.3758 0.025 Uiso 1 1 calc R U . . .
C3 C 0.22354(17) 0.66352(5) 0.48612(16) 0.0232(3) Uani 1 1 d . . . . .
H3A H 0.3452 0.6708 0.4876 0.028 Uiso 1 1 calc R U . . .
H3B H 0.1538 0.6956 0.4406 0.028 Uiso 1 1 calc R U . . .
C4 C 0.21142(17) 0.65571(5) 0.64830(16) 0.0226(3) Uani 1 1 d . . . . .
H4A H 0.0883 0.6543 0.6486 0.027 Uiso 1 1 calc R U . . .
H4B H 0.2657 0.6871 0.7113 0.027 Uiso 1 1 calc R U . . .
C5 C 0.30096(16) 0.60351(5) 0.71724(15) 0.0199(3) Uani 1 1 d . . . . .
H5A H 0.2851 0.5985 0.8205 0.024 Uiso 1 1 calc R U . . .
H5B H 0.4264 0.6066 0.7275 0.024 Uiso 1 1 calc R U . . .
C6 C 0.22946(15) 0.55390(5) 0.61933(14) 0.0149(3) Uani 1 1 d . . . . .
H6 H 0.1033 0.5504 0.6113 0.018 Uiso 1 1 calc R U . . .
C7 C 0.28936(15) 0.48914(5) 0.83544(14) 0.0175(3) Uani 1 1 d . . . . .
H7A H 0.3056 0.5215 0.9027 0.021 Uiso 1 1 calc R U . . .
H7B H 0.1690 0.4762 0.8191 0.021 Uiso 1 1 calc R U . . .
C8 C 0.39430(15) 0.40148(5) 0.81793(14) 0.0168(3) Uani 1 1 d . . . . .
C9 C 0.44010(16) 0.35104(5) 0.88602(16) 0.0215(3) Uani 1 1 d . . . . .
H9 H 0.4814 0.3483 0.9938 0.026 Uiso 1 1 calc R U . . .
C10 C 0.42553(16) 0.30482(5) 0.79682(16) 0.0220(3) Uani 1 1 d . . . . .
H10 H 0.4555 0.2705 0.8446 0.026 Uiso 1 1 calc R U . . .
C11 C 0.36784(16) 0.30753(5) 0.63829(16) 0.0193(3) Uani 1 1 d . . . . .
C12 C 0.32523(15) 0.35925(5) 0.56881(15) 0.0155(3) Uani 1 1 d . . . . .
C13 C 0.33684(15) 0.40673(5) 0.65995(14) 0.0142(3) Uani 1 1 d . . . . .
C14 C 0.29557(14) 0.45918(5) 0.59088(14) 0.0133(3) Uani 1 1 d . . . . .
C15 C 0.24003(14) 0.46391(5) 0.43664(14) 0.0129(3) Uani 1 1 d . . . . .
C16 C 0.22947(14) 0.41647(5) 0.34264(14) 0.0147(3) Uani 1 1 d . . . . .
C17 C 0.27247(15) 0.36445(5) 0.40848(14) 0.0151(3) Uani 1 1 d . . . . .
C18 C 0.26044(16) 0.31766(5) 0.31393(16) 0.0191(3) Uani 1 1 d . . . . .
C19 C 0.30418(17) 0.26595(5) 0.38700(17) 0.0230(3) Uani 1 1 d . . . . .
H19 H 0.2985 0.2343 0.3259 0.028 Uiso 1 1 calc R U . . .
C20 C 0.35316(17) 0.26105(5) 0.53994(16) 0.0231(3) Uani 1 1 d . . . . .
H20 H 0.3787 0.2259 0.5839 0.028 Uiso 1 1 calc R U . . .
C21 C 0.20214(16) 0.32474(5) 0.15612(15) 0.0225(3) Uani 1 1 d . . . . .
H21 H 0.1943 0.2940 0.0913 0.027 Uiso 1 1 calc R U . . .
C22 C 0.15550(16) 0.37541(6) 0.09197(15) 0.0221(3) Uani 1 1 d . . . . .
H22 H 0.1137 0.3791 -0.0155 0.026 Uiso 1 1 calc R U . . .
C23 C 0.16985(15) 0.42079(5) 0.18491(14) 0.0173(3) Uani 1 1 d . . . . .
C24 C 0.21512(16) 0.51420(5) 0.21095(14) 0.0184(3) Uani 1 1 d . . . . .
H24A H 0.1757 0.5494 0.1605 0.022 Uiso 1 1 calc R U . . .
H24B H 0.3402 0.5104 0.2199 0.022 Uiso 1 1 calc R U . . .


_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 C8 1.3716(15) . ?
O1 C7 1.4334(14) . ?
O2 C23 1.3679(15) . ?
O2 C24 1.4273(15) . ?
N1 C14 1.4014(15) . ?
N1 C7 1.4591(15) . ?
N1 C6 1.4753(15) . ?
N2 C15 1.4068(14) . ?
N2 C24 1.4618(15) . ?
N2 C1 1.4782(15) . ?
C1 C2 1.5298(16) . ?
C1 C6 1.5387(17) . ?
C1 H1 1.0000 . ?
C2 C3 1.5258(18) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.5180(19) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5207(17) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.5276(16) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6 1.0000 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.3898(17) . ?
C8 C13 1.3934(17) . ?
C9 C10 1.3823(19) . ?
C9 H9 0.9500 . ?
C10 C11 1.3939(19) . ?
C10 H10 0.9500 . ?
C11 C12 1.4193(17) . ?
C11 C20 1.4361(18) . ?
C12 C17 1.4122(18) . ?
C12 C13 1.4195(17) . ?
C13 C14 1.4328(16) . ?
C14 C15 1.3594(17) . ?
C15 C16 1.4346(16) . ?
C16 C23 1.3904(18) . ?
C16 C17 1.4142(17) . ?
C17 C18 1.4234(17) . ?
C18 C21 1.3972(19) . ?
C18 C19 1.4330(18) . ?
C19 C20 1.347(2) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C22 1.3831(18) . ?
C21 H21 0.9500 . ?
C22 C23 1.3854(18) . ?
C22 H22 0.9500 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O1 C7 112.56(9) . . ?
C23 O2 C24 112.54(9) . . ?
C14 N1 C7 111.06(10) . . ?
C14 N1 C6 114.20(9) . . ?
C7 N1 C6 114.98(9) . . ?
C15 N2 C24 110.66(9) . . ?
C15 N2 C1 113.43(9) . . ?
C24 N2 C1 115.39(9) . . ?
N2 C1 C2 110.65(10) . . ?
N2 C1 C6 109.96(9) . . ?
C2 C1 C6 109.18(10) . . ?
N2 C1 H1 109.0 . . ?
C2 C1 H1 109.0 . . ?
C6 C1 H1 109.0 . . ?
C3 C2 C1 111.76(10) . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
C4 C3 C2 111.55(10) . . ?
C4 C3 H3A 109.3 . . ?
C2 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
C3 C4 C5 111.17(10) . . ?
C3 C4 H4A 109.4 . . ?
C5 C4 H4A 109.4 . . ?
C3 C4 H4B 109.4 . . ?
C5 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C4 C5 C6 111.70(11) . . ?
C4 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 107.9 . . ?
N1 C6 C5 110.27(10) . . ?
N1 C6 C1 110.09(9) . . ?
C5 C6 C1 109.29(10) . . ?
N1 C6 H6 109.1 . . ?
C5 C6 H6 109.1 . . ?
C1 C6 H6 109.1 . . ?
O1 C7 N1 110.33(9) . . ?
O1 C7 H7A 109.6 . . ?
N1 C7 H7A 109.6 . . ?
O1 C7 H7B 109.6 . . ?
N1 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
O1 C8 C9 119.67(11) . . ?
O1 C8 C13 119.18(11) . . ?
C9 C8 C13 121.15(12) . . ?
C10 C9 C8 119.96(12) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 121.42(12) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C10 C11 C12 118.52(12) . . ?
C10 C11 C20 123.81(12) . . ?
C12 C11 C20 117.65(12) . . ?
C17 C12 C11 120.73(11) . . ?
C17 C12 C13 118.97(11) . . ?
C11 C12 C13 120.30(12) . . ?
C8 C13 C12 118.62(11) . . ?
C8 C13 C14 120.63(11) . . ?
C12 C13 C14 120.72(11) . . ?
C15 C14 N1 122.98(11) . . ?
C15 C14 C13 120.21(11) . . ?
N1 C14 C13 116.79(11) . . ?
C14 C15 N2 122.69(11) . . ?
C14 C15 C16 119.82(11) . . ?
N2 C15 C16 117.47(11) . . ?
C23 C16 C17 118.93(11) . . ?
C23 C16 C15 120.19(11) . . ?
C17 C16 C15 120.82(11) . . ?
C12 C17 C16 119.41(11) . . ?
C12 C17 C18 120.33(11) . . ?
C16 C17 C18 120.26(12) . . ?
C21 C18 C17 118.10(12) . . ?
C21 C18 C19 124.07(12) . . ?
C17 C18 C19 117.80(12) . . ?
C20 C19 C18 121.75(12) . . ?
C20 C19 H19 119.1 . . ?
C18 C19 H19 119.1 . . ?
C19 C20 C11 121.73(12) . . ?
C19 C20 H20 119.1 . . ?
C11 C20 H20 119.1 . . ?
C22 C21 C18 121.60(12) . . ?
C22 C21 H21 119.2 . . ?
C18 C21 H21 119.2 . . ?
C21 C22 C23 119.83(12) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
O2 C23 C22 119.42(12) . . ?
O2 C23 C16 119.35(11) . . ?
C22 C23 C16 121.23(12) . . ?
O2 C24 N2 110.71(10) . . ?
O2 C24 H24A 109.5 . . ?
N2 C24 H24A 109.5 . . ?
O2 C24 H24B 109.5 . . ?
N2 C24 H24B 109.5 . . ?
H24A C24 H24B 108.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N2 C1 C2 -166.76(10) . . . . ?
C24 N2 C1 C2 64.08(13) . . . . ?
C15 N2 C1 C6 -46.07(12) . . . . ?
C24 N2 C1 C6 -175.23(9) . . . . ?
N2 C1 C2 C3 178.97(10) . . . . ?
C6 C1 C2 C3 57.82(13) . . . . ?
C1 C2 C3 C4 -54.96(14) . . . . ?
C2 C3 C4 C5 52.97(14) . . . . ?
C3 C4 C5 C6 -55.73(14) . . . . ?
C14 N1 C6 C5 -164.23(10) . . . . ?
C7 N1 C6 C5 65.69(13) . . . . ?
C14 N1 C6 C1 -43.56(13) . . . . ?
C7 N1 C6 C1 -173.64(9) . . . . ?
C4 C5 C6 N1 -179.99(10) . . . . ?
C4 C5 C6 C1 58.87(13) . . . . ?
N2 C1 C6 N1 58.13(12) . . . . ?
C2 C1 C6 N1 179.70(9) . . . . ?
N2 C1 C6 C5 179.39(9) . . . . ?
C2 C1 C6 C5 -59.04(13) . . . . ?
C8 O1 C7 N1 -57.58(12) . . . . ?
C14 N1 C7 O1 59.73(12) . . . . ?
C6 N1 C7 O1 -168.67(9) . . . . ?
C7 O1 C8 C9 -153.61(11) . . . . ?
C7 O1 C8 C13 26.90(15) . . . . ?
O1 C8 C9 C10 179.16(11) . . . . ?
C13 C8 C9 C10 -1.37(19) . . . . ?
C8 C9 C10 C11 1.0(2) . . . . ?
C9 C10 C11 C12 0.59(19) . . . . ?
C9 C10 C11 C20 178.83(11) . . . . ?
C10 C11 C12 C17 177.58(11) . . . . ?
C20 C11 C12 C17 -0.77(18) . . . . ?
C10 C11 C12 C13 -1.77(18) . . . . ?
C20 C11 C12 C13 179.88(11) . . . . ?
O1 C8 C13 C12 179.66(10) . . . . ?
C9 C8 C13 C12 0.18(18) . . . . ?
O1 C8 C13 C14 1.60(17) . . . . ?
C9 C8 C13 C14 -177.87(11) . . . . ?
C17 C12 C13 C8 -177.97(10) . . . . ?
C11 C12 C13 C8 1.39(17) . . . . ?
C17 C12 C13 C14 0.08(17) . . . . ?
C11 C12 C13 C14 179.44(10) . . . . ?
C7 N1 C14 C15 150.11(11) . . . . ?
C6 N1 C14 C15 18.11(16) . . . . ?
C7 N1 C14 C13 -31.22(13) . . . . ?
C6 N1 C14 C13 -163.22(10) . . . . ?
C8 C13 C14 C15 179.83(11) . . . . ?
C12 C13 C14 C15 1.82(18) . . . . ?
C8 C13 C14 N1 1.12(17) . . . . ?
C12 C13 C14 N1 -176.89(10) . . . . ?
N1 C14 C15 N2 -5.66(18) . . . . ?
C13 C14 C15 N2 175.71(9) . . . . ?
N1 C14 C15 C16 176.09(10) . . . . ?
C13 C14 C15 C16 -2.54(17) . . . . ?
C24 N2 C15 C14 152.27(11) . . . . ?
C1 N2 C15 C14 20.75(16) . . . . ?
C24 N2 C15 C16 -29.44(13) . . . . ?
C1 N2 C15 C16 -160.96(10) . . . . ?
C14 C15 C16 C23 178.84(11) . . . . ?
N2 C15 C16 C23 0.50(17) . . . . ?
C14 C15 C16 C17 1.44(17) . . . . ?
N2 C15 C16 C17 -176.90(10) . . . . ?
C11 C12 C17 C16 179.47(10) . . . . ?
C13 C12 C17 C16 -1.17(17) . . . . ?
C11 C12 C17 C18 0.31(18) . . . . ?
C13 C12 C17 C18 179.67(10) . . . . ?
C23 C16 C17 C12 -176.98(11) . . . . ?
C15 C16 C17 C12 0.45(17) . . . . ?
C23 C16 C17 C18 2.18(18) . . . . ?
C15 C16 C17 C18 179.62(10) . . . . ?
C12 C17 C18 C21 177.92(11) . . . . ?
C16 C17 C18 C21 -1.24(18) . . . . ?
C12 C17 C18 C19 -0.30(18) . . . . ?
C16 C17 C18 C19 -179.45(11) . . . . ?
C21 C18 C19 C20 -177.27(12) . . . . ?
C17 C18 C19 C20 0.83(19) . . . . ?
C18 C19 C20 C11 -1.4(2) . . . . ?
C10 C11 C20 C19 -176.95(12) . . . . ?
C12 C11 C20 C19 1.31(19) . . . . ?
C17 C18 C21 C22 -0.58(19) . . . . ?
C19 C18 C21 C22 177.51(11) . . . . ?
C18 C21 C22 C23 1.4(2) . . . . ?
C24 O2 C23 C22 -152.14(11) . . . . ?
C24 O2 C23 C16 28.40(15) . . . . ?
C21 C22 C23 O2 -179.90(11) . . . . ?
C21 C22 C23 C16 -0.45(19) . . . . ?
C17 C16 C23 O2 178.11(10) . . . . ?
C15 C16 C23 O2 0.66(18) . . . . ?
C17 C16 C23 C22 -1.34(19) . . . . ?
C15 C16 C23 C22 -178.79(10) . . . . ?
C23 O2 C24 N2 -58.33(13) . . . . ?
C15 N2 C24 O2 58.47(12) . . . . ?
C1 N2 C24 O2 -171.03(9) . . . . ?

_refine_diff_density_max         0.465
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.072



####################################################################### 
# 
# 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_g027
_database_code_depnum_ccdc_archive 'CCDC 1502357'
_audit_update_record             
;
2016-09-02 deposited with the CCDC.
2018-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H22 N2 O2'
_chemical_formula_weight         466.51

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

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

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

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

_cell_length_a                   5.3397(5)
_cell_length_b                   12.5882(10)
_cell_length_c                   17.1650(13)
_cell_angle_alpha                95.560(3)
_cell_angle_beta                 94.461(3)
_cell_angle_gamma                101.447(3)
_cell_volume                     1119.93(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3512
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      28.13

_exptl_crystal_description       Block
_exptl_crystal_colour            Pale_Yellow
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.516
_exptl_crystal_size_mid          0.301
_exptl_crystal_size_min          0.126
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5524
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16981
_diffrn_reflns_av_unetI/netI     0.0799
_diffrn_reflns_av_R_equivalents  0.0820
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.396
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             4443
_reflns_number_gt                2578
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0810P)²+3.5087P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4443
_refine_ls_number_parameters     448
_refine_ls_number_restraints     539
_refine_ls_R_factor_all          0.1775
_refine_ls_R_factor_gt           0.1105
_refine_ls_wR_factor_ref         0.2798
_refine_ls_wR_factor_gt          0.2431
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8519(18) 0.6414(7) 0.6356(4) 0.0258(14) Uani 0.578(10) 1 d D U P A 1
H1A H 0.9884 0.6398 0.5999 0.031 Uiso 0.578(10) 1 calc R U P A 1
H1B H 0.7116 0.5772 0.6186 0.031 Uiso 0.578(10) 1 calc R U P A 1
C2 C 0.9599(17) 0.6357(9) 0.7196(5) 0.0254(14) Uani 0.578(10) 1 d D U P A 1
H2A H 1.0187 0.5662 0.7224 0.030 Uiso 0.578(10) 1 calc R U P A 1
H2B H 1.1097 0.6964 0.7350 0.030 Uiso 0.578(10) 1 calc R U P A 1
C1A C 0.960(2) 0.6801(10) 0.6531(7) 0.0259(15) Uani 0.422(10) 1 d D U P A 2
H1A1 H 1.1146 0.7341 0.6770 0.031 Uiso 0.422(10) 1 calc R U P A 2
H1A2 H 1.0073 0.6422 0.6048 0.031 Uiso 0.422(10) 1 calc R U P A 2
C2A C 0.889(3) 0.5981(10) 0.7094(7) 0.0258(15) Uani 0.422(10) 1 d D U P A 2
H2A1 H 0.7710 0.5327 0.6810 0.031 Uiso 0.422(10) 1 calc R U P A 2
H2A2 H 1.0452 0.5754 0.7307 0.031 Uiso 0.422(10) 1 calc R U P A 2
C3 C 0.8305(12) 0.6190(6) 0.8517(3) 0.0328(9) Uani 0.656(5) 1 d D U P A 1
H3 H 1.0025 0.6648 0.8722 0.039 Uiso 0.656(5) 1 calc R U P A 1
C4 C 0.8410(15) 0.4979(6) 0.8518(5) 0.0350(8) Uani 0.656(5) 1 d D U P A 1
C5 C 1.0449(14) 0.4650(6) 0.8914(4) 0.0364(8) Uani 0.656(5) 1 d D U P A 1
H5 H 1.1880 0.5176 0.9166 0.044 Uiso 0.656(5) 1 calc R U P A 1
C6 C 1.0362(14) 0.3519(6) 0.8935(4) 0.0367(8) Uani 0.656(5) 1 d D U P A 1
H6 H 1.1731 0.3282 0.9208 0.044 Uiso 0.656(5) 1 calc R U P A 1
C7 C 0.8310(14) 0.2776(6) 0.8564(4) 0.0366(9) Uani 0.656(5) 1 d D U P A 1
H7 H 0.8245 0.2020 0.8582 0.044 Uiso 0.656(5) 1 calc R U P A 1
C8 C 0.6322(13) 0.3111(6) 0.8160(4) 0.0366(9) Uani 0.656(5) 1 d D U P A 1
H8 H 0.4911 0.2584 0.7898 0.044 Uiso 0.656(5) 1 calc R U P A 1
C9 C 0.6370(14) 0.4209(6) 0.8136(4) 0.0361(8) Uani 0.656(5) 1 d D U P A 1
H9 H 0.4997 0.4434 0.7857 0.043 Uiso 0.656(5) 1 calc R U P A 1
C3A C 0.662(2) 0.5778(6) 0.8319(4) 0.0358(9) Uani 0.344(5) 1 d D U P A 2
H3A H 0.4851 0.5380 0.8110 0.043 Uiso 0.344(5) 1 calc R U P A 2
C4A C 0.814(2) 0.4957(7) 0.8545(7) 0.0352(8) Uani 0.344(5) 1 d DG U P A 2
C5A C 1.0379(19) 0.5046(6) 0.9038(6) 0.0356(9) Uani 0.344(5) 1 d G U P A 2
H5A H 1.1305 0.5744 0.9269 0.043 Uiso 0.344(5) 1 calc R U P A 2
C6A C 1.1266(16) 0.4115(8) 0.9194(5) 0.0355(9) Uani 0.344(5) 1 d G U P A 2
H6A H 1.2797 0.4176 0.9531 0.043 Uiso 0.344(5) 1 calc R U P A 2
C7A C 0.991(2) 0.3094(7) 0.8856(6) 0.0361(9) Uani 0.344(5) 1 d G U P A 2
H7A H 1.0518 0.2457 0.8962 0.043 Uiso 0.344(5) 1 calc R U P A 2
C8A C 0.7671(19) 0.3005(7) 0.8362(6) 0.0364(9) Uani 0.344(5) 1 d G U P A 2
H8A H 0.6746 0.2307 0.8131 0.044 Uiso 0.344(5) 1 calc R U P A 2
C9A C 0.6785(17) 0.3936(9) 0.8207(6) 0.0360(9) Uani 0.344(5) 1 d G U P A 2
H9A H 0.5253 0.3876 0.7870 0.043 Uiso 0.344(5) 1 calc R U P A 2
C10 C 0.8246(12) 0.8126(5) 0.5746(3) 0.0383(10) Uani 0.695(7) 1 d D U P A 1
H10 H 0.9908 0.8630 0.5952 0.046 Uiso 0.695(7) 1 calc R U P A 1
C11 C 0.8571(14) 0.7569(7) 0.4944(4) 0.0409(9) Uani 0.695(7) 1 d D U P A 1
C12 C 0.6667(15) 0.6735(7) 0.4566(4) 0.0440(9) Uani 0.695(7) 1 d D U P A 1
H12 H 0.5146 0.6505 0.4810 0.053 Uiso 0.695(7) 1 calc R U P A 1
C13 C 0.6943(15) 0.6218(7) 0.3822(4) 0.0453(10) Uani 0.695(7) 1 d D U P A 1
H13 H 0.5644 0.5630 0.3571 0.054 Uiso 0.695(7) 1 calc R U P A 1
C14 C 0.9118(14) 0.6577(7) 0.3466(4) 0.0428(9) Uani 0.695(7) 1 d D U P A 1
H14 H 0.9345 0.6233 0.2966 0.051 Uiso 0.695(7) 1 calc R U P A 1
C15 C 1.0956(15) 0.7429(7) 0.3833(5) 0.0431(9) Uani 0.695(7) 1 d D U P A 1
H15 H 1.2452 0.7686 0.3584 0.052 Uiso 0.695(7) 1 calc R U P A 1
C16 C 1.0642(15) 0.7918(7) 0.4563(4) 0.0425(9) Uani 0.695(7) 1 d D U P A 1
H16 H 1.1923 0.8520 0.4805 0.051 Uiso 0.695(7) 1 calc R U P A 1
C10A C 0.646(2) 0.7644(6) 0.5590(4) 0.0403(11) Uani 0.305(7) 1 d D U P A 2
H10A H 0.4650 0.7219 0.5500 0.048 Uiso 0.305(7) 1 calc R U P A 2
C11A C 0.785(3) 0.7302(11) 0.4911(6) 0.0413(9) Uani 0.305(7) 1 d DG U P A 2
C12A C 0.677(2) 0.6263(11) 0.4539(7) 0.0430(10) Uani 0.305(7) 1 d DG U P A 2
H12A H 0.5415 0.5813 0.4756 0.052 Uiso 0.305(7) 1 calc R U P A 2
C13A C 0.767(3) 0.5883(9) 0.3850(7) 0.0432(10) Uani 0.305(7) 1 d G U P A 2
H13A H 0.6935 0.5173 0.3595 0.052 Uiso 0.305(7) 1 calc R U P A 2
C14A C 0.965(3) 0.6543(10) 0.3533(6) 0.0433(10) Uani 0.305(7) 1 d G U P A 2
H14A H 1.0270 0.6283 0.3062 0.052 Uiso 0.305(7) 1 calc R U P A 2
C15A C 1.073(2) 0.7582(10) 0.3905(8) 0.0429(10) Uani 0.305(7) 1 d G U P A 2
H15A H 1.2084 0.8032 0.3688 0.051 Uiso 0.305(7) 1 calc R U P A 2
C16A C 0.983(3) 0.7961(9) 0.4594(7) 0.0421(10) Uani 0.305(7) 1 d DG U P A 2
H16A H 1.0563 0.8672 0.4849 0.051 Uiso 0.305(7) 1 calc R U P A 2
O1 O 0.6473(6) 0.6373(3) 0.90537(16) 0.0318(8) Uani 1 1 d D . . . .
O2 O 0.6386(6) 0.8766(3) 0.55840(16) 0.0351(8) Uani 1 1 d D . . . .
N1 N 0.7644(7) 0.6425(3) 0.7745(2) 0.0318(9) Uani 1 1 d D . . . .
N2 N 0.7558(7) 0.7392(3) 0.63067(19) 0.0306(9) Uani 1 1 d D . . . .
C17 C 0.5541(8) 0.7318(4) 0.9017(2) 0.0276(10) Uani 1 1 d . . . . .
C18 C 0.4433(9) 0.7713(4) 0.9665(3) 0.0354(12) Uani 1 1 d . . . . .
H18 H 0.4457 0.7373 1.0135 0.043 Uiso 1 1 calc R U . . .
C19 C 0.3305(10) 0.8599(4) 0.9616(3) 0.0372(12) Uani 1 1 d . . . . .
H19 H 0.2541 0.8863 1.0057 0.045 Uiso 1 1 calc R U . . .
C20 C 0.3252(10) 0.9124(4) 0.8935(3) 0.0355(12) Uani 1 1 d . . . . .
C21 C 0.4450(8) 0.8721(4) 0.8286(2) 0.0258(10) Uani 1 1 d . . . . .
C22 C 0.5611(8) 0.7812(4) 0.8334(2) 0.0234(9) Uani 1 1 d . . . . .
C23 C 0.6702(7) 0.7375(3) 0.7676(2) 0.0219(9) Uani 1 1 d . . . . .
C24 C 0.6667(8) 0.7838(4) 0.6988(2) 0.0243(10) Uani 1 1 d . . . . .
C25 C 0.5549(8) 0.8773(4) 0.6933(2) 0.0259(10) Uani 1 1 d . . . . .
C26 C 0.4416(8) 0.9213(3) 0.7573(2) 0.0266(10) Uani 1 1 d . . . . .
C27 C 0.3156(10) 1.0081(4) 0.7497(3) 0.0368(12) Uani 1 1 d . . . . .
C28 C 0.1954(12) 1.0467(4) 0.8151(3) 0.0492(15) Uani 1 1 d . . . . .
H28 H 0.1104 1.1057 0.8105 0.059 Uiso 1 1 calc R U . . .
C29 C 0.1992(11) 1.0018(4) 0.8832(3) 0.0453(14) Uani 1 1 d . . . . .
H29 H 0.1170 1.0298 0.9254 0.054 Uiso 1 1 calc R U . . .
C30 C 0.3143(11) 1.0527(4) 0.6776(3) 0.0462(14) Uani 1 1 d . . . . .
H30 H 0.2363 1.1134 0.6720 0.055 Uiso 1 1 calc R U . . .
C31 C 0.4243(11) 1.0098(4) 0.6147(3) 0.0429(13) Uani 1 1 d . . . . .
H31 H 0.4185 1.0399 0.5661 0.051 Uiso 1 1 calc R U . . .
C32 C 0.5437(9) 0.9222(4) 0.6231(2) 0.0305(11) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.431(8) . ?
C1 C2 1.525(11) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 N1 1.468(8) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C1A N2 1.486(10) . ?
C1A C2A 1.496(15) . ?
C1A H1A1 0.9900 . ?
C1A H1A2 0.9900 . ?
C2A N1 1.464(10) . ?
C2A H2A1 0.9900 . ?
C2A H2A2 0.9900 . ?
C3 N1 1.419(5) . ?
C3 O1 1.431(5) . ?
C3 C4 1.537(9) . ?
C3 H3 1.0000 . ?
C4 C9 1.379(9) . ?
C4 C5 1.391(8) . ?
C5 C6 1.419(9) . ?
C5 H5 0.9500 . ?
C6 C7 1.360(9) . ?
C6 H6 0.9500 . ?
C7 C8 1.380(8) . ?
C7 H7 0.9500 . ?
C8 C9 1.382(9) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C3A N1 1.413(6) . ?
C3A O1 1.419(6) . ?
C3A C4A 1.495(11) . ?
C3A H3A 1.0000 . ?
C4A C5A 1.3900 . ?
C4A C9A 1.3900 . ?
C5A C6A 1.3900 . ?
C5A H5A 0.9500 . ?
C6A C7A 1.3900 . ?
C6A H6A 0.9500 . ?
C7A C8A 1.3900 . ?
C7A H7A 0.9500 . ?
C8A C9A 1.3900 . ?
C8A H8A 0.9500 . ?
C9A H9A 0.9500 . ?
C10 N2 1.417(5) . ?
C10 O2 1.426(5) . ?
C10 C11 1.521(8) . ?
C10 H10 1.0000 . ?
C11 C16 1.349(8) . ?
C11 C12 1.378(9) . ?
C12 C13 1.407(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.372(8) . ?
C13 H13 0.9500 . ?
C14 C15 1.366(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.380(8) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C10A N2 1.413(6) . ?
C10A O2 1.422(6) . ?
C10A C11A 1.501(11) . ?
C10A H10A 1.0000 . ?
C11A C12A 1.3900 . ?
C11A C16A 1.3900 . ?
C12A C13A 1.3900 . ?
C12A H12A 0.9500 . ?
C13A C14A 1.3900 . ?
C13A H13A 0.9500 . ?
C14A C15A 1.3900 . ?
C14A H14A 0.9500 . ?
C15A C16A 1.3900 . ?
C15A H15A 0.9500 . ?
C16A H16A 0.9500 . ?
O1 C17 1.382(5) . ?
O2 C32 1.378(5) . ?
N1 C23 1.398(6) . ?
N2 C24 1.406(5) . ?
C17 C22 1.380(6) . ?
C17 C18 1.394(6) . ?
C18 C19 1.376(7) . ?
C18 H18 0.9500 . ?
C19 C20 1.398(7) . ?
C19 H19 0.9500 . ?
C20 C21 1.428(6) . ?
C20 C29 1.439(7) . ?
C21 C22 1.412(6) . ?
C21 C26 1.423(6) . ?
C22 C23 1.424(5) . ?
C23 C24 1.366(6) . ?
C24 C25 1.429(6) . ?
C25 C32 1.383(6) . ?
C25 C26 1.414(5) . ?
C26 C27 1.403(6) . ?
C27 C30 1.407(7) . ?
C27 C28 1.429(6) . ?
C28 C29 1.348(7) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C30 C31 1.383(6) . ?
C30 H30 0.9500 . ?
C31 C32 1.392(7) . ?
C31 H31 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 C2 110.6(7) . . ?
N2 C1 H1A 109.5 . . ?
C2 C1 H1A 109.5 . . ?
N2 C1 H1B 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 108.1 . . ?
N1 C2 C1 110.8(7) . . ?
N1 C2 H2A 109.5 . . ?
C1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
N2 C1A C2A 114.6(9) . . ?
N2 C1A H1A1 108.6 . . ?
C2A C1A H1A1 108.6 . . ?
N2 C1A H1A2 108.6 . . ?
C2A C1A H1A2 108.6 . . ?
H1A1 C1A H1A2 107.6 . . ?
N1 C2A C1A 111.6(10) . . ?
N1 C2A H2A1 109.3 . . ?
C1A C2A H2A1 109.3 . . ?
N1 C2A H2A2 109.3 . . ?
C1A C2A H2A2 109.3 . . ?
H2A1 C2A H2A2 108.0 . . ?
N1 C3 O1 113.4(4) . . ?
N1 C3 C4 110.8(5) . . ?
O1 C3 C4 105.0(5) . . ?
N1 C3 H3 109.2 . . ?
O1 C3 H3 109.2 . . ?
C4 C3 H3 109.2 . . ?
C9 C4 C5 120.0(6) . . ?
C9 C4 C3 118.2(6) . . ?
C5 C4 C3 121.8(7) . . ?
C4 C5 C6 119.2(6) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C7 C6 C5 119.7(6) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C6 C7 C8 120.7(6) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C7 C8 C9 120.4(6) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C4 C9 C8 120.1(6) . . ?
C4 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
N1 C3A O1 114.6(5) . . ?
N1 C3A C4A 114.8(9) . . ?
O1 C3A C4A 102.7(7) . . ?
N1 C3A H3A 108.2 . . ?
O1 C3A H3A 108.2 . . ?
C4A C3A H3A 108.2 . . ?
C5A C4A C9A 120.0 . . ?
C5A C4A C3A 132.3(8) . . ?
C9A C4A C3A 107.5(8) . . ?
C4A C5A C6A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
C6A C5A H5A 120.0 . . ?
C7A C6A C5A 120.0 . . ?
C7A C6A H6A 120.0 . . ?
C5A C6A H6A 120.0 . . ?
C6A C7A C8A 120.0 . . ?
C6A C7A H7A 120.0 . . ?
C8A C7A H7A 120.0 . . ?
C7A C8A C9A 120.0 . . ?
C7A C8A H8A 120.0 . . ?
C9A C8A H8A 120.0 . . ?
C8A C9A C4A 120.0 . . ?
C8A C9A H9A 120.0 . . ?
C4A C9A H9A 120.0 . . ?
N2 C10 O2 113.5(4) . . ?
N2 C10 C11 113.8(5) . . ?
O2 C10 C11 104.3(5) . . ?
N2 C10 H10 108.3 . . ?
O2 C10 H10 108.3 . . ?
C11 C10 H10 108.3 . . ?
C16 C11 C12 118.1(6) . . ?
C16 C11 C10 121.2(6) . . ?
C12 C11 C10 120.5(6) . . ?
C11 C12 C13 121.0(6) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 118.9(6) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C15 C14 C13 119.8(6) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 120.1(6) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C11 C16 C15 122.0(7) . . ?
C11 C16 H16 119.0 . . ?
C15 C16 H16 119.0 . . ?
N2 C10A O2 113.9(5) . . ?
N2 C10A C11A 111.2(9) . . ?
O2 C10A C11A 108.6(9) . . ?
N2 C10A H10A 107.6 . . ?
O2 C10A H10A 107.6 . . ?
C11A C10A H10A 107.6 . . ?
C12A C11A C16A 120.0 . . ?
C12A C11A C10A 113.6(9) . . ?
C16A C11A C10A 126.0(9) . . ?
C11A C12A C13A 120.0 . . ?
C11A C12A H12A 120.0 . . ?
C13A C12A H12A 120.0 . . ?
C14A C13A C12A 120.0 . . ?
C14A C13A H13A 120.0 . . ?
C12A C13A H13A 120.0 . . ?
C13A C14A C15A 120.0 . . ?
C13A C14A H14A 120.0 . . ?
C15A C14A H14A 120.0 . . ?
C14A C15A C16A 120.0 . . ?
C14A C15A H15A 120.0 . . ?
C16A C15A H15A 120.0 . . ?
C15A C16A C11A 120.0 . . ?
C15A C16A H16A 120.0 . . ?
C11A C16A H16A 120.0 . . ?
C17 O1 C3A 115.8(5) . . ?
C17 O1 C3 116.5(4) . . ?
C32 O2 C10A 114.7(5) . . ?
C32 O2 C10 115.8(4) . . ?
C23 N1 C3A 115.7(5) . . ?
C23 N1 C3 117.1(4) . . ?
C23 N1 C2A 119.2(6) . . ?
C3A N1 C2A 122.0(6) . . ?
C23 N1 C2 109.7(5) . . ?
C3 N1 C2 115.1(5) . . ?
C24 N2 C10A 115.3(5) . . ?
C24 N2 C10 115.5(4) . . ?
C24 N2 C1 117.1(4) . . ?
C10 N2 C1 123.5(5) . . ?
C24 N2 C1A 109.6(5) . . ?
C10A N2 C1A 135.0(7) . . ?
C22 C17 O1 119.6(4) . . ?
C22 C17 C18 121.9(4) . . ?
O1 C17 C18 118.5(4) . . ?
C19 C18 C17 119.3(4) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C18 C19 C20 121.8(4) . . ?
C18 C19 H19 119.1 . . ?
C20 C19 H19 119.1 . . ?
C19 C20 C21 117.8(4) . . ?
C19 C20 C29 124.5(4) . . ?
C21 C20 C29 117.6(4) . . ?
C22 C21 C26 119.3(4) . . ?
C22 C21 C20 120.5(4) . . ?
C26 C21 C20 120.2(4) . . ?
C17 C22 C21 118.6(4) . . ?
C17 C22 C23 120.6(4) . . ?
C21 C22 C23 120.7(4) . . ?
C24 C23 N1 121.8(3) . . ?
C24 C23 C22 120.4(4) . . ?
N1 C23 C22 117.7(4) . . ?
C23 C24 N2 122.4(4) . . ?
C23 C24 C25 119.7(4) . . ?
N2 C24 C25 117.7(4) . . ?
C32 C25 C26 119.0(4) . . ?
C32 C25 C24 119.8(4) . . ?
C26 C25 C24 121.1(4) . . ?
C27 C26 C25 120.7(4) . . ?
C27 C26 C21 120.4(4) . . ?
C25 C26 C21 118.8(4) . . ?
C26 C27 C30 118.1(4) . . ?
C26 C27 C28 118.6(4) . . ?
C30 C27 C28 123.3(5) . . ?
C29 C28 C27 121.8(5) . . ?
C29 C28 H28 119.1 . . ?
C27 C28 H28 119.1 . . ?
C28 C29 C20 121.5(4) . . ?
C28 C29 H29 119.3 . . ?
C20 C29 H29 119.3 . . ?
C31 C30 C27 121.3(5) . . ?
C31 C30 H30 119.3 . . ?
C27 C30 H30 119.3 . . ?
C30 C31 C32 119.6(5) . . ?
C30 C31 H31 120.2 . . ?
C32 C31 H31 120.2 . . ?
O2 C32 C25 120.1(4) . . ?
O2 C32 C31 118.6(4) . . ?
C25 C32 C31 121.1(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C1 C2 N1 56.8(11) . . . . ?
N2 C1A C2A N1 -45.9(15) . . . . ?
N1 C3 C4 C9 -49.1(8) . . . . ?
O1 C3 C4 C9 73.7(8) . . . . ?
N1 C3 C4 C5 133.1(7) . . . . ?
O1 C3 C4 C5 -104.1(7) . . . . ?
C9 C4 C5 C6 -1.6(10) . . . . ?
C3 C4 C5 C6 176.1(7) . . . . ?
C4 C5 C6 C7 0.7(10) . . . . ?
C5 C6 C7 C8 0.6(10) . . . . ?
C6 C7 C8 C9 -0.9(10) . . . . ?
C5 C4 C9 C8 1.4(10) . . . . ?
C3 C4 C9 C8 -176.4(7) . . . . ?
C7 C8 C9 C4 -0.1(10) . . . . ?
N1 C3A C4A C5A 78.8(10) . . . . ?
O1 C3A C4A C5A -46.2(11) . . . . ?
N1 C3A C4A C9A -106.1(7) . . . . ?
O1 C3A C4A C9A 128.9(6) . . . . ?
C9A C4A C5A C6A 0.0 . . . . ?
C3A C4A C5A C6A 174.6(12) . . . . ?
C4A C5A C6A C7A 0.0 . . . . ?
C5A C6A C7A C8A 0.0 . . . . ?
C6A C7A C8A C9A 0.0 . . . . ?
C7A C8A C9A C4A 0.0 . . . . ?
C5A C4A C9A C8A 0.0 . . . . ?
C3A C4A C9A C8A -175.8(10) . . . . ?
N2 C10 C11 C16 -132.4(8) . . . . ?
O2 C10 C11 C16 103.4(8) . . . . ?
N2 C10 C11 C12 51.8(10) . . . . ?
O2 C10 C11 C12 -72.4(9) . . . . ?
C16 C11 C12 C13 3.8(12) . . . . ?
C10 C11 C12 C13 179.7(7) . . . . ?
C11 C12 C13 C14 -1.8(13) . . . . ?
C12 C13 C14 C15 -0.6(13) . . . . ?
C13 C14 C15 C16 0.9(13) . . . . ?
C12 C11 C16 C15 -3.5(13) . . . . ?
C10 C11 C16 C15 -179.4(8) . . . . ?
C14 C15 C16 C11 1.2(13) . . . . ?
N2 C10A C11A C12A 93.0(10) . . . . ?
O2 C10A C11A C12A -140.9(9) . . . . ?
N2 C10A C11A C16A -94.5(10) . . . . ?
O2 C10A C11A C16A 31.6(13) . . . . ?
C16A C11A C12A C13A 0.0 . . . . ?
C10A C11A C12A C13A 173.0(12) . . . . ?
C11A C12A C13A C14A 0.0 . . . . ?
C12A C13A C14A C15A 0.0 . . . . ?
C13A C14A C15A C16A 0.0 . . . . ?
C14A C15A C16A C11A 0.0 . . . . ?
C12A C11A C16A C15A 0.0 . . . . ?
C10A C11A C16A C15A -172.1(14) . . . . ?
N1 C3A O1 C17 44.2(10) . . . . ?
C4A C3A O1 C17 169.3(6) . . . . ?
N1 C3 O1 C17 -43.3(7) . . . . ?
C4 C3 O1 C17 -164.4(5) . . . . ?
N2 C10A O2 C32 -48.0(11) . . . . ?
C11A C10A O2 C32 -172.6(7) . . . . ?
N2 C10 O2 C32 45.6(7) . . . . ?
C11 C10 O2 C32 170.0(5) . . . . ?
O1 C3A N1 C23 -45.0(10) . . . . ?
C4A C3A N1 C23 -163.5(6) . . . . ?
O1 C3A N1 C2A 155.1(9) . . . . ?
C4A C3A N1 C2A 36.6(12) . . . . ?
O1 C3 N1 C23 42.8(7) . . . . ?
C4 C3 N1 C23 160.6(5) . . . . ?
O1 C3 N1 C2 174.0(6) . . . . ?
C4 C3 N1 C2 -68.2(8) . . . . ?
C1A C2A N1 C23 15.9(14) . . . . ?
C1A C2A N1 C3A 175.2(10) . . . . ?
C1 C2 N1 C23 -55.8(9) . . . . ?
C1 C2 N1 C3 169.5(7) . . . . ?
O2 C10A N2 C24 46.9(11) . . . . ?
C11A C10A N2 C24 170.1(7) . . . . ?
O2 C10A N2 C1A -128.8(10) . . . . ?
C11A C10A N2 C1A -5.6(14) . . . . ?
O2 C10 N2 C24 -46.9(7) . . . . ?
C11 C10 N2 C24 -165.9(5) . . . . ?
O2 C10 N2 C1 155.8(6) . . . . ?
C11 C10 N2 C1 36.8(9) . . . . ?
C2 C1 N2 C24 -28.1(10) . . . . ?
C2 C1 N2 C10 128.9(7) . . . . ?
C2A C1A N2 C24 52.0(12) . . . . ?
C2A C1A N2 C10A -132.1(11) . . . . ?
C3A O1 C17 C22 -20.8(7) . . . . ?
C3 O1 C17 C22 23.3(6) . . . . ?
C3A O1 C17 C18 155.9(6) . . . . ?
C3 O1 C17 C18 -159.9(5) . . . . ?
C22 C17 C18 C19 2.0(7) . . . . ?
O1 C17 C18 C19 -174.6(4) . . . . ?
C17 C18 C19 C20 -0.5(8) . . . . ?
C18 C19 C20 C21 -0.9(8) . . . . ?
C18 C19 C20 C29 176.7(5) . . . . ?
C19 C20 C21 C22 0.9(7) . . . . ?
C29 C20 C21 C22 -176.9(5) . . . . ?
C19 C20 C21 C26 179.0(4) . . . . ?
C29 C20 C21 C26 1.1(7) . . . . ?
O1 C17 C22 C21 174.6(4) . . . . ?
C18 C17 C22 C21 -2.1(6) . . . . ?
O1 C17 C22 C23 -1.9(6) . . . . ?
C18 C17 C22 C23 -178.5(4) . . . . ?
C26 C21 C22 C17 -177.5(4) . . . . ?
C20 C21 C22 C17 0.6(6) . . . . ?
C26 C21 C22 C23 -1.1(6) . . . . ?
C20 C21 C22 C23 177.0(4) . . . . ?
C3A N1 C23 C24 -153.7(6) . . . . ?
C3 N1 C23 C24 161.8(5) . . . . ?
C2A N1 C23 C24 6.9(8) . . . . ?
C2 N1 C23 C24 28.2(6) . . . . ?
C3A N1 C23 C22 22.3(7) . . . . ?
C3 N1 C23 C22 -22.2(6) . . . . ?
C2A N1 C23 C22 -177.1(7) . . . . ?
C2 N1 C23 C22 -155.8(5) . . . . ?
C17 C22 C23 C24 177.2(4) . . . . ?
C21 C22 C23 C24 0.8(6) . . . . ?
C17 C22 C23 N1 1.1(6) . . . . ?
C21 C22 C23 N1 -175.2(4) . . . . ?
N1 C23 C24 N2 0.4(6) . . . . ?
C22 C23 C24 N2 -175.5(4) . . . . ?
N1 C23 C24 C25 176.4(4) . . . . ?
C22 C23 C24 C25 0.5(6) . . . . ?
C10A N2 C24 C23 154.1(6) . . . . ?
C10 N2 C24 C23 -158.7(5) . . . . ?
C1 N2 C24 C23 0.1(7) . . . . ?
C1A N2 C24 C23 -29.2(7) . . . . ?
C10A N2 C24 C25 -22.0(7) . . . . ?
C10 N2 C24 C25 25.2(6) . . . . ?
C1 N2 C24 C25 -176.0(6) . . . . ?
C1A N2 C24 C25 154.7(6) . . . . ?
C23 C24 C25 C32 -177.9(4) . . . . ?
N2 C24 C25 C32 -1.7(6) . . . . ?
C23 C24 C25 C26 -1.5(6) . . . . ?
N2 C24 C25 C26 174.7(4) . . . . ?
C32 C25 C26 C27 1.1(7) . . . . ?
C24 C25 C26 C27 -175.3(4) . . . . ?
C32 C25 C26 C21 177.6(4) . . . . ?
C24 C25 C26 C21 1.2(6) . . . . ?
C22 C21 C26 C27 176.6(4) . . . . ?
C20 C21 C26 C27 -1.5(7) . . . . ?
C22 C21 C26 C25 0.1(6) . . . . ?
C20 C21 C26 C25 -178.0(4) . . . . ?
C25 C26 C27 C30 -2.5(7) . . . . ?
C21 C26 C27 C30 -179.0(5) . . . . ?
C25 C26 C27 C28 177.5(5) . . . . ?
C21 C26 C27 C28 1.0(7) . . . . ?
C26 C27 C28 C29 -0.3(9) . . . . ?
C30 C27 C28 C29 179.7(6) . . . . ?
C27 C28 C29 C20 0.0(9) . . . . ?
C19 C20 C29 C28 -178.1(6) . . . . ?
C21 C20 C29 C28 -0.5(8) . . . . ?
C26 C27 C30 C31 2.6(8) . . . . ?
C28 C27 C30 C31 -177.4(6) . . . . ?
C27 C30 C31 C32 -1.4(9) . . . . ?
C10A O2 C32 C25 24.3(7) . . . . ?
C10 O2 C32 C25 -22.5(6) . . . . ?
C10A O2 C32 C31 -152.1(6) . . . . ?
C10 O2 C32 C31 161.1(5) . . . . ?
C26 C25 C32 O2 -176.0(4) . . . . ?
C24 C25 C32 O2 0.4(7) . . . . ?
C26 C25 C32 C31 0.3(7) . . . . ?
C24 C25 C32 C31 176.7(5) . . . . ?
C30 C31 C32 O2 176.2(5) . . . . ?
C30 C31 C32 C25 -0.1(8) . . . . ?

_refine_diff_density_max         0.582
_refine_diff_density_min         -0.658
_refine_diff_density_rms         0.072



