# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_ba_a
_database_code_depnum_ccdc_archive 'CCDC 2015832'
loop_
_audit_author_name
_audit_author_address
'Jiacheng Zou'
;Tongji University
China
;
_audit_update_record             
;
2020-07-13 deposited with the CCDC.	2021-03-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
2,8-bis((E)-2-(pyridin-2-yl)vinyl)-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine
_chemical_name_common            TBOP
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H24 N4'
_chemical_formula_sum            'C29 H24 N4'
_chemical_formula_weight         428.52

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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'

_cell_length_a                   15.6255(10)
_cell_length_b                   6.0517(4)
_cell_length_c                   47.672(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4507.9(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    9859
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      67.80

_exptl_crystal_description       block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_F_000             1808
_exptl_transmission_factor_min   0.6333
_exptl_transmission_factor_max   0.7531
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.588
_shelx_estimated_absorpt_T_min   0.891
_shelx_estimated_absorpt_T_max   0.917
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            64635
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -57
_diffrn_reflns_limit_l_max       55
_diffrn_reflns_theta_min         3.709
_diffrn_reflns_theta_max         68.474
_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 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             8195
_reflns_number_gt                6568
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.954
_reflns_Friedel_fraction_max     0.975
_reflns_Friedel_fraction_full    0.980

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1312P)²+0.3926P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0027(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 2699 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(2)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         8195
_refine_ls_number_parameters     596
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0637
_refine_ls_wR_factor_ref         0.1920
_refine_ls_wR_factor_gt          0.1730
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.023
_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 0.2096(3) -0.0157(8) 0.22233(11) 0.0887(12) Uani 1 1 d . . . . .
C1 C 0.2037(3) -0.1653(9) 0.20056(13) 0.0843(14) Uani 1 1 d . . . . .
H1 H 0.174426 -0.297508 0.203113 0.101 Uiso 1 1 calc R U . . .
N2 N 0.2513(2) 0.9458(6) 0.35592(8) 0.0653(9) Uani 1 1 d . . . . .
C2 C 0.2411(4) -0.1191(10) 0.17513(13) 0.0894(16) Uani 1 1 d . . . . .
H2 H 0.238226 -0.220116 0.160462 0.107 Uiso 1 1 calc R U . . .
N3 N 0.2009(2) 0.6654(6) 0.38792(8) 0.0677(10) Uani 1 1 d . . . . .
C3 C 0.2825(4) 0.0785(12) 0.17179(14) 0.1008(18) Uani 1 1 d . . . . .
H3 H 0.306330 0.112205 0.154441 0.121 Uiso 1 1 calc R U . . .
C4 C 0.2897(3) 0.2255(9) 0.19287(12) 0.0803(14) Uani 1 1 d . . . . .
H4 H 0.319451 0.357063 0.190277 0.096 Uiso 1 1 calc R U . . .
N4 N 0.7145(4) 0.5426(11) 0.45792(11) 0.1070(16) Uani 1 1 d . U . . .
N6 N 0.0104(2) 0.0563(6) 0.64455(8) 0.0665(9) Uani 1 1 d . . . . .
C6 C 0.2634(3) 0.3408(8) 0.24027(10) 0.0709(11) Uani 1 1 d . . . . .
H6 H 0.295856 0.465847 0.236322 0.085 Uiso 1 1 calc R U . . .
N5 N 0.4309(3) 0.7900(10) 0.52582(11) 0.1009(15) Uani 1 1 d . . . . .
C5 C 0.2534(3) 0.1791(8) 0.21768(10) 0.0659(10) Uani 1 1 d . . . . .
N7 N -0.0386(2) 0.3382(6) 0.61242(8) 0.0674(9) Uani 1 1 d . . . . .
C7 C 0.2309(3) 0.3257(7) 0.26565(10) 0.0660(10) Uani 1 1 d . . . . .
H7 H 0.198726 0.199643 0.269357 0.079 Uiso 1 1 calc R U . . .
C8 C 0.2392(3) 0.4843(7) 0.28882(9) 0.0604(10) Uani 1 1 d . . . . .
N8 N 0.0486(3) 0.7702(8) 0.80798(11) 0.0929(14) Uani 1 1 d . . . . .
C9 C 0.2052(3) 0.4323(7) 0.31469(9) 0.0634(10) Uani 1 1 d . . . . .
H9 H 0.178263 0.296503 0.317081 0.076 Uiso 1 1 calc R U . . .
C10 C 0.2100(3) 0.5786(7) 0.33753(9) 0.0600(9) Uani 1 1 d . . . . .
C12 C 0.2853(3) 0.8365(7) 0.30768(10) 0.0673(11) Uani 1 1 d . . . . .
H12 H 0.312669 0.971604 0.305332 0.081 Uiso 1 1 calc R U . . .
C11 C 0.2484(3) 0.7822(7) 0.33372(10) 0.0603(10) Uani 1 1 d . . . . .
C14 C 0.1749(3) 0.5109(7) 0.36576(10) 0.0683(11) Uani 1 1 d . . . . .
H14A H 0.112915 0.505714 0.364822 0.082 Uiso 1 1 calc R U . . .
H14B H 0.195278 0.363925 0.370350 0.082 Uiso 1 1 calc R U . . .
C13 C 0.2808(3) 0.6914(9) 0.28597(10) 0.0686(11) Uani 1 1 d . . . . .
H13 H 0.305524 0.728739 0.268869 0.082 Uiso 1 1 calc R U . . .
C15 C 0.1895(3) 0.8901(7) 0.37777(11) 0.0708(11) Uani 1 1 d . . . . .
H15A H 0.195827 0.992315 0.393300 0.085 Uiso 1 1 calc R U . . .
H15B H 0.131996 0.906284 0.370368 0.085 Uiso 1 1 calc R U . . .
C16 C 0.3347(3) 0.9666(7) 0.36898(10) 0.0683(11) Uani 1 1 d . . . . .
H16A H 0.338143 1.107482 0.378608 0.082 Uiso 1 1 calc R U . . .
H16B H 0.378499 0.964783 0.354542 0.082 Uiso 1 1 calc R U . . .
C17 C 0.3523(3) 0.7802(7) 0.38995(9) 0.0641(10) Uani 1 1 d . . . . .
C19 C 0.3069(3) 0.4585(7) 0.41521(10) 0.0730(12) Uani 1 1 d . . . . .
H19 H 0.264041 0.359067 0.420097 0.088 Uiso 1 1 calc R U . . .
C18 C 0.2879(3) 0.6356(7) 0.39722(9) 0.0624(10) Uani 1 1 d . . . . .
C20 C 0.3870(3) 0.4311(8) 0.42554(10) 0.0763(12) Uani 1 1 d . . . . .
H20 H 0.398463 0.308958 0.436767 0.092 Uiso 1 1 calc R U . . .
C21 C 0.4535(3) 0.5812(8) 0.41982(10) 0.0721(11) Uani 1 1 d . . . . .
C22 C 0.4334(3) 0.7554(8) 0.40163(11) 0.0692(12) Uani 1 1 d . . . . .
H22 H 0.475601 0.857974 0.397222 0.083 Uiso 1 1 calc R U . . .
C23 C 0.5389(3) 0.5611(9) 0.43196(10) 0.0757(12) Uani 1 1 d . . . . .
H23 H 0.575206 0.681648 0.429764 0.091 Uiso 1 1 calc R U . . .
C24 C 0.5697(4) 0.3921(10) 0.44554(12) 0.0857(14) Uani 1 1 d . . . . .
H24 H 0.534680 0.268005 0.446617 0.103 Uiso 1 1 calc R U . . .
C25 C 0.6539(3) 0.3756(9) 0.45942(10) 0.0787(12) Uani 1 1 d . U . . .
C26 C 0.6664(3) 0.1908(9) 0.47408(11) 0.0795(13) Uani 1 1 d . . . . .
H26 H 0.626081 0.077855 0.474147 0.095 Uiso 1 1 calc R U . . .
C27 C 0.7394(5) 0.1738(14) 0.48873(15) 0.110(2) Uani 1 1 d . . . . .
H27 H 0.748213 0.047106 0.499393 0.132 Uiso 1 1 calc R U . . .
C28 C 0.8017(5) 0.3336(14) 0.48880(16) 0.112(2) Uani 1 1 d . . . . .
H28 H 0.851431 0.315360 0.499256 0.134 Uiso 1 1 calc R U . . .
C29 C 0.7892(4) 0.5177(14) 0.47338(15) 0.1032(19) Uani 1 1 d . . . . .
H29 H 0.830588 0.628042 0.473112 0.124 Uiso 1 1 calc R U . . .
C30 C 0.5083(6) 0.8137(16) 0.51345(14) 0.115(2) Uani 1 1 d . . . . .
H30 H 0.519857 0.942848 0.503584 0.138 Uiso 1 1 calc R U . . .
C31 C 0.5702(5) 0.6534(19) 0.51499(16) 0.128(3) Uani 1 1 d . . . . .
H31 H 0.622653 0.672683 0.506101 0.154 Uiso 1 1 calc R U . . .
C32 C 0.5534(4) 0.4641(14) 0.52987(16) 0.111(2) Uani 1 1 d . . . . .
H32 H 0.594486 0.353444 0.531408 0.133 Uiso 1 1 calc R U . . .
C33 C 0.4759(4) 0.4416(11) 0.54229(13) 0.0925(15) Uani 1 1 d . . . . .
H33 H 0.463507 0.313691 0.552315 0.111 Uiso 1 1 calc R U . . .
C34 C 0.4161(3) 0.6036(10) 0.54026(11) 0.0821(13) Uani 1 1 d . . . . .
C35 C 0.3306(3) 0.5966(10) 0.55345(11) 0.0827(13) Uani 1 1 d . . . . .
H35 H 0.295498 0.719375 0.551111 0.099 Uiso 1 1 calc R U . . .
C36 C 0.2998(3) 0.4298(10) 0.56833(10) 0.0800(13) Uani 1 1 d . . . . .
H36 H 0.336247 0.310307 0.571064 0.096 Uiso 1 1 calc R U . . .
C37 C 0.2145(3) 0.4128(8) 0.58096(10) 0.0711(11) Uani 1 1 d . . . . .
C38 C 0.1940(3) 0.2407(8) 0.59884(11) 0.0693(12) Uani 1 1 d . . . . .
H38 H 0.236025 0.136968 0.603038 0.083 Uiso 1 1 calc R U . . .
C39 C 0.1135(3) 0.2157(7) 0.61080(9) 0.0642(10) Uani 1 1 d . . . . .
C40 C 0.0490(3) 0.3674(7) 0.60318(10) 0.0644(10) Uani 1 1 d . . . . .
C41 C 0.0685(3) 0.5429(8) 0.58577(10) 0.0706(11) Uani 1 1 d . . . . .
H41 H 0.026256 0.644869 0.581163 0.085 Uiso 1 1 calc R U . . .
C42 C 0.1498(3) 0.5682(8) 0.57521(11) 0.0771(12) Uani 1 1 d . . . . .
H42 H 0.162210 0.690187 0.564067 0.093 Uiso 1 1 calc R U . . .
C43 C 0.0945(3) 0.0341(7) 0.63140(10) 0.0696(11) Uani 1 1 d . . . . .
H43A H 0.097430 -0.106940 0.621779 0.083 Uiso 1 1 calc R U . . .
H43B H 0.138093 0.034409 0.645889 0.083 Uiso 1 1 calc R U . . .
C44 C -0.0498(3) 0.1137(7) 0.62259(11) 0.0706(12) Uani 1 1 d . . . . .
H44A H -0.107590 0.096979 0.629711 0.085 Uiso 1 1 calc R U . . .
H44B H -0.042803 0.011775 0.607056 0.085 Uiso 1 1 calc R U . . .
C45 C -0.0644(3) 0.4903(7) 0.63459(10) 0.0659(10) Uani 1 1 d . . . . .
H45A H -0.126375 0.495793 0.635439 0.079 Uiso 1 1 calc R U . . .
H45B H -0.043971 0.637428 0.630058 0.079 Uiso 1 1 calc R U . . .
C46 C -0.0302(3) 0.4242(7) 0.66276(10) 0.0627(10) Uani 1 1 d . . . . .
C47 C 0.0085(3) 0.2207(7) 0.66677(10) 0.0608(10) Uani 1 1 d . . . . .
C48 C 0.0442(3) 0.1649(7) 0.69257(10) 0.0678(11) Uani 1 1 d . . . . .
H48 H 0.071037 0.028971 0.694847 0.081 Uiso 1 1 calc R U . . .
C49 C 0.0398(3) 0.3103(8) 0.71473(10) 0.0690(11) Uani 1 1 d . . . . .
H49 H 0.064402 0.271906 0.731812 0.083 Uiso 1 1 calc R U . . .
C50 C -0.0012(3) 0.5153(7) 0.71197(10) 0.0622(10) Uani 1 1 d . . . . .
C51 C -0.0348(3) 0.5681(7) 0.68559(9) 0.0631(10) Uani 1 1 d . . . . .
H51 H -0.061283 0.704471 0.683186 0.076 Uiso 1 1 calc R U . . .
C52 C -0.0084(3) 0.6713(8) 0.73492(10) 0.0671(10) Uani 1 1 d . . . . .
H52 H -0.039191 0.799274 0.731086 0.081 Uiso 1 1 calc R U . . .
C53 C 0.0232(3) 0.6555(8) 0.76065(11) 0.0724(11) Uani 1 1 d . . . . .
H53 H 0.054072 0.528755 0.765034 0.087 Uiso 1 1 calc R U . . .
C54 C 0.0133(3) 0.8221(8) 0.78274(10) 0.0676(11) Uani 1 1 d . . . . .
C55 C -0.0307(3) 1.0153(8) 0.77865(10) 0.0712(11) Uani 1 1 d . . . . .
H55 H -0.056311 1.046445 0.761485 0.085 Uiso 1 1 calc R U . . .
C56 C -0.0359(4) 1.1599(8) 0.80034(14) 0.0873(16) Uani 1 1 d . . . . .
H56 H -0.065275 1.292188 0.797880 0.105 Uiso 1 1 calc R U . . .
C57 C 0.0012(4) 1.1151(10) 0.82589(13) 0.0889(16) Uani 1 1 d . . . . .
H57 H -0.002436 1.214860 0.840685 0.107 Uiso 1 1 calc R U . . .
C58 C 0.0420(4) 0.9258(11) 0.82864(13) 0.0981(17) Uani 1 1 d . . . . .
H58 H 0.068086 0.896234 0.845768 0.118 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
N1 C1 1.380(7) . ?
N1 C5 1.380(6) . ?
C1 C2 1.374(9) . ?
C1 H1 0.9300 . ?
N2 C11 1.450(6) . ?
N2 C16 1.451(6) . ?
N2 C15 1.460(6) . ?
C2 C3 1.369(9) . ?
C2 H2 0.9300 . ?
N3 C18 1.441(6) . ?
N3 C15 1.454(5) . ?
N3 C14 1.468(6) . ?
C3 C4 1.347(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.342(7) . ?
C4 H4 0.9300 . ?
N4 C25 1.387(8) . ?
N4 C29 1.388(8) . ?
N6 C44 1.449(6) . ?
N6 C47 1.453(6) . ?
N6 C43 1.463(6) . ?
C6 C7 1.316(7) . ?
C6 C5 1.464(6) . ?
C6 H6 0.9300 . ?
N5 C34 1.342(7) . ?
N5 C30 1.353(9) . ?
N7 C40 1.450(6) . ?
N7 C44 1.453(6) . ?
N7 C45 1.458(6) . ?
C7 C8 1.470(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.380(6) . ?
C8 C13 1.418(7) . ?
N8 C54 1.360(7) . ?
N8 C58 1.367(8) . ?
C9 C10 1.405(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.382(6) . ?
C10 C14 1.510(6) . ?
C12 C13 1.359(6) . ?
C12 C11 1.407(7) . ?
C12 H12 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C13 H13 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.532(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.378(6) . ?
C17 C22 1.391(7) . ?
C19 C20 1.356(7) . ?
C19 C18 1.404(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.406(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.401(7) . ?
C21 C23 1.461(7) . ?
C22 H22 0.9300 . ?
C23 C24 1.302(8) . ?
C23 H23 0.9300 . ?
C24 C25 1.477(8) . ?
C24 H24 0.9300 . ?
C25 C26 1.333(7) . ?
C26 C27 1.340(8) . ?
C26 H26 0.9300 . ?
C27 C28 1.372(11) . ?
C27 H27 0.9300 . ?
C28 C29 1.349(11) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C30 C31 1.372(12) . ?
C30 H30 0.9300 . ?
C31 C32 1.373(12) . ?
C31 H31 0.9300 . ?
C32 C33 1.355(9) . ?
C32 H32 0.9300 . ?
C33 C34 1.358(8) . ?
C33 H33 0.9300 . ?
C34 C35 1.478(7) . ?
C35 C36 1.324(8) . ?
C35 H35 0.9300 . ?
C36 C37 1.466(7) . ?
C36 H36 0.9300 . ?
C37 C38 1.383(7) . ?
C37 C42 1.408(7) . ?
C38 C39 1.390(7) . ?
C38 H38 0.9300 . ?
C39 C40 1.410(6) . ?
C39 C43 1.503(6) . ?
C40 C41 1.382(6) . ?
C41 C42 1.374(7) . ?
C41 H41 0.9300 . ?
C42 H42 0.9300 . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C44 H44A 0.9700 . ?
C44 H44B 0.9700 . ?
C45 C46 1.500(7) . ?
C45 H45A 0.9700 . ?
C45 H45B 0.9700 . ?
C46 C47 1.386(6) . ?
C46 C51 1.396(6) . ?
C47 C48 1.392(6) . ?
C48 C49 1.376(7) . ?
C48 H48 0.9300 . ?
C49 C50 1.402(6) . ?
C49 H49 0.9300 . ?
C50 C51 1.400(6) . ?
C50 C52 1.450(6) . ?
C51 H51 0.9300 . ?
C52 C53 1.326(7) . ?
C52 H52 0.9300 . ?
C53 C54 1.466(6) . ?
C53 H53 0.9300 . ?
C54 C55 1.371(7) . ?
C55 C56 1.357(7) . ?
C55 H55 0.9300 . ?
C56 C57 1.376(9) . ?
C56 H56 0.9300 . ?
C57 C58 1.318(9) . ?
C57 H57 0.9300 . ?
C58 H58 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 118.2(5) . . ?
C2 C1 N1 120.1(5) . . ?
C2 C1 H1 120.0 . . ?
N1 C1 H1 120.0 . . ?
C11 N2 C16 113.6(3) . . ?
C11 N2 C15 110.0(3) . . ?
C16 N2 C15 108.0(4) . . ?
C3 C2 C1 118.7(5) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C18 N3 C15 109.6(4) . . ?
C18 N3 C14 113.8(3) . . ?
C15 N3 C14 108.8(4) . . ?
C4 C3 C2 122.0(6) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C5 C4 C3 118.9(5) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C25 N4 C29 117.9(6) . . ?
C44 N6 C47 110.5(3) . . ?
C44 N6 C43 107.2(4) . . ?
C47 N6 C43 113.1(3) . . ?
C7 C6 C5 126.0(4) . . ?
C7 C6 H6 117.0 . . ?
C5 C6 H6 117.0 . . ?
C34 N5 C30 117.8(7) . . ?
C4 C5 N1 122.0(5) . . ?
C4 C5 C6 117.6(5) . . ?
N1 C5 C6 120.4(4) . . ?
C40 N7 C44 109.2(4) . . ?
C40 N7 C45 113.8(3) . . ?
C44 N7 C45 108.4(4) . . ?
C6 C7 C8 127.7(4) . . ?
C6 C7 H7 116.2 . . ?
C8 C7 H7 116.2 . . ?
C9 C8 C13 117.7(4) . . ?
C9 C8 C7 119.2(4) . . ?
C13 C8 C7 123.1(4) . . ?
C54 N8 C58 116.6(5) . . ?
C8 C9 C10 121.9(4) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 H9 119.1 . . ?
C11 C10 C9 118.9(4) . . ?
C11 C10 C14 121.1(4) . . ?
C9 C10 C14 120.0(4) . . ?
C13 C12 C11 120.0(4) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C10 C11 C12 120.1(4) . . ?
C10 C11 N2 121.8(4) . . ?
C12 C11 N2 118.1(4) . . ?
N3 C14 C10 111.6(3) . . ?
N3 C14 H14A 109.3 . . ?
C10 C14 H14A 109.3 . . ?
N3 C14 H14B 109.3 . . ?
C10 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
C12 C13 C8 121.4(4) . . ?
C12 C13 H13 119.3 . . ?
C8 C13 H13 119.3 . . ?
N3 C15 N2 111.8(3) . . ?
N3 C15 H15A 109.2 . . ?
N2 C15 H15A 109.2 . . ?
N3 C15 H15B 109.2 . . ?
N2 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
N2 C16 C17 112.2(4) . . ?
N2 C16 H16A 109.2 . . ?
C17 C16 H16A 109.2 . . ?
N2 C16 H16B 109.2 . . ?
C17 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C18 C17 C22 119.7(4) . . ?
C18 C17 C16 120.0(4) . . ?
C22 C17 C16 120.3(4) . . ?
C20 C19 C18 120.7(4) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C17 C18 C19 118.9(4) . . ?
C17 C18 N3 122.1(4) . . ?
C19 C18 N3 118.9(4) . . ?
C19 C20 C21 122.2(4) . . ?
C19 C20 H20 118.9 . . ?
C21 C20 H20 118.9 . . ?
C22 C21 C20 116.2(4) . . ?
C22 C21 C23 120.9(4) . . ?
C20 C21 C23 123.0(5) . . ?
C17 C22 C21 122.2(4) . . ?
C17 C22 H22 118.9 . . ?
C21 C22 H22 118.9 . . ?
C24 C23 C21 126.8(5) . . ?
C24 C23 H23 116.6 . . ?
C21 C23 H23 116.6 . . ?
C23 C24 C25 127.2(6) . . ?
C23 C24 H24 116.4 . . ?
C25 C24 H24 116.4 . . ?
C26 C25 N4 122.6(5) . . ?
C26 C25 C24 115.0(5) . . ?
N4 C25 C24 122.4(5) . . ?
C25 C26 C27 117.5(6) . . ?
C25 C26 H26 121.2 . . ?
C27 C26 H26 121.2 . . ?
C26 C27 C28 123.4(7) . . ?
C26 C27 H27 118.3 . . ?
C28 C27 H27 118.3 . . ?
C29 C28 C27 118.6(7) . . ?
C29 C28 H28 120.7 . . ?
C27 C28 H28 120.7 . . ?
C28 C29 N4 120.0(7) . . ?
C28 C29 H29 120.0 . . ?
N4 C29 H29 120.0 . . ?
N5 C30 C31 122.1(8) . . ?
N5 C30 H30 118.9 . . ?
C31 C30 H30 118.9 . . ?
C30 C31 C32 118.9(7) . . ?
C30 C31 H31 120.6 . . ?
C32 C31 H31 120.6 . . ?
C33 C32 C31 118.7(7) . . ?
C33 C32 H32 120.7 . . ?
C31 C32 H32 120.7 . . ?
C32 C33 C34 120.8(7) . . ?
C32 C33 H33 119.6 . . ?
C34 C33 H33 119.6 . . ?
N5 C34 C33 121.7(5) . . ?
N5 C34 C35 113.5(5) . . ?
C33 C34 C35 124.8(5) . . ?
C36 C35 C34 125.3(5) . . ?
C36 C35 H35 117.3 . . ?
C34 C35 H35 117.3 . . ?
C35 C36 C37 127.2(5) . . ?
C35 C36 H36 116.4 . . ?
C37 C36 H36 116.4 . . ?
C38 C37 C42 117.2(4) . . ?
C38 C37 C36 121.1(4) . . ?
C42 C37 C36 121.7(4) . . ?
C37 C38 C39 123.0(4) . . ?
C37 C38 H38 118.5 . . ?
C39 C38 H38 118.5 . . ?
C38 C39 C40 118.0(4) . . ?
C38 C39 C43 121.7(4) . . ?
C40 C39 C43 120.2(4) . . ?
C41 C40 C39 119.8(4) . . ?
C41 C40 N7 119.0(4) . . ?
C39 C40 N7 121.1(4) . . ?
C42 C41 C40 120.6(4) . . ?
C42 C41 H41 119.7 . . ?
C40 C41 H41 119.7 . . ?
C41 C42 C37 121.2(4) . . ?
C41 C42 H42 119.4 . . ?
C37 C42 H42 119.4 . . ?
N6 C43 C39 113.0(4) . . ?
N6 C43 H43A 109.0 . . ?
C39 C43 H43A 109.0 . . ?
N6 C43 H43B 109.0 . . ?
C39 C43 H43B 109.0 . . ?
H43A C43 H43B 107.8 . . ?
N6 C44 N7 112.8(3) . . ?
N6 C44 H44A 109.0 . . ?
N7 C44 H44A 109.0 . . ?
N6 C44 H44B 109.0 . . ?
N7 C44 H44B 109.0 . . ?
H44A C44 H44B 107.8 . . ?
N7 C45 C46 112.5(3) . . ?
N7 C45 H45A 109.1 . . ?
C46 C45 H45A 109.1 . . ?
N7 C45 H45B 109.1 . . ?
C46 C45 H45B 109.1 . . ?
H45A C45 H45B 107.8 . . ?
C47 C46 C51 118.0(4) . . ?
C47 C46 C45 121.1(4) . . ?
C51 C46 C45 120.9(4) . . ?
C46 C47 C48 120.8(4) . . ?
C46 C47 N6 121.1(4) . . ?
C48 C47 N6 118.1(4) . . ?
C49 C48 C47 120.2(4) . . ?
C49 C48 H48 119.9 . . ?
C47 C48 H48 119.9 . . ?
C48 C49 C50 121.1(4) . . ?
C48 C49 H49 119.5 . . ?
C50 C49 H49 119.5 . . ?
C51 C50 C49 117.3(4) . . ?
C51 C50 C52 120.0(4) . . ?
C49 C50 C52 122.7(4) . . ?
C46 C51 C50 122.6(4) . . ?
C46 C51 H51 118.7 . . ?
C50 C51 H51 118.7 . . ?
C53 C52 C50 128.5(4) . . ?
C53 C52 H52 115.7 . . ?
C50 C52 H52 115.7 . . ?
C52 C53 C54 125.2(4) . . ?
C52 C53 H53 117.4 . . ?
C54 C53 H53 117.4 . . ?
N8 C54 C55 121.8(5) . . ?
N8 C54 C53 115.7(4) . . ?
C55 C54 C53 122.5(5) . . ?
C56 C55 C54 118.1(5) . . ?
C56 C55 H55 120.9 . . ?
C54 C55 H55 120.9 . . ?
C55 C56 C57 121.5(5) . . ?
C55 C56 H56 119.3 . . ?
C57 C56 H56 119.3 . . ?
C58 C57 C56 117.6(5) . . ?
C58 C57 H57 121.2 . . ?
C56 C57 H57 121.2 . . ?
C57 C58 N8 124.3(6) . . ?
C57 C58 H58 117.8 . . ?
N8 C58 H58 117.8 . . ?

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
C5 N1 C1 C2 0.3(7) . . . . ?
N1 C1 C2 C3 -1.2(8) . . . . ?
C1 C2 C3 C4 1.9(10) . . . . ?
C2 C3 C4 C5 -1.7(10) . . . . ?
C3 C4 C5 N1 0.8(8) . . . . ?
C3 C4 C5 C6 179.2(5) . . . . ?
C1 N1 C5 C4 -0.1(7) . . . . ?
C1 N1 C5 C6 -178.4(4) . . . . ?
C7 C6 C5 C4 178.4(5) . . . . ?
C7 C6 C5 N1 -3.1(7) . . . . ?
C5 C6 C7 C8 -179.8(4) . . . . ?
C6 C7 C8 C9 -175.6(5) . . . . ?
C6 C7 C8 C13 4.7(7) . . . . ?
C13 C8 C9 C10 0.8(6) . . . . ?
C7 C8 C9 C10 -179.0(4) . . . . ?
C8 C9 C10 C11 1.4(6) . . . . ?
C8 C9 C10 C14 -177.6(4) . . . . ?
C9 C10 C11 C12 -2.8(6) . . . . ?
C14 C10 C11 C12 176.2(4) . . . . ?
C9 C10 C11 N2 176.5(4) . . . . ?
C14 C10 C11 N2 -4.5(6) . . . . ?
C13 C12 C11 C10 2.1(7) . . . . ?
C13 C12 C11 N2 -177.3(4) . . . . ?
C16 N2 C11 C10 104.9(5) . . . . ?
C15 N2 C11 C10 -16.3(6) . . . . ?
C16 N2 C11 C12 -75.8(5) . . . . ?
C15 N2 C11 C12 163.1(4) . . . . ?
C18 N3 C14 C10 -77.6(4) . . . . ?
C15 N3 C14 C10 44.9(5) . . . . ?
C11 C10 C14 N3 -10.3(5) . . . . ?
C9 C10 C14 N3 168.6(4) . . . . ?
C11 C12 C13 C8 0.2(7) . . . . ?
C9 C8 C13 C12 -1.6(6) . . . . ?
C7 C8 C13 C12 178.2(4) . . . . ?
C18 N3 C15 N2 55.1(5) . . . . ?
C14 N3 C15 N2 -69.9(5) . . . . ?
C11 N2 C15 N3 53.5(5) . . . . ?
C16 N2 C15 N3 -71.0(5) . . . . ?
C11 N2 C16 C17 -78.3(4) . . . . ?
C15 N2 C16 C17 44.0(5) . . . . ?
N2 C16 C17 C18 -8.5(6) . . . . ?
N2 C16 C17 C22 171.2(4) . . . . ?
C22 C17 C18 C19 -3.4(6) . . . . ?
C16 C17 C18 C19 176.3(4) . . . . ?
C22 C17 C18 N3 174.0(4) . . . . ?
C16 C17 C18 N3 -6.4(6) . . . . ?
C20 C19 C18 C17 0.7(7) . . . . ?
C20 C19 C18 N3 -176.7(4) . . . . ?
C15 N3 C18 C17 -16.2(6) . . . . ?
C14 N3 C18 C17 105.8(4) . . . . ?
C15 N3 C18 C19 161.1(4) . . . . ?
C14 N3 C18 C19 -76.8(5) . . . . ?
C18 C19 C20 C21 2.7(8) . . . . ?
C19 C20 C21 C22 -3.1(7) . . . . ?
C19 C20 C21 C23 176.6(5) . . . . ?
C18 C17 C22 C21 2.9(7) . . . . ?
C16 C17 C22 C21 -176.8(4) . . . . ?
C20 C21 C22 C17 0.4(7) . . . . ?
C23 C21 C22 C17 -179.4(4) . . . . ?
C22 C21 C23 C24 -168.8(5) . . . . ?
C20 C21 C23 C24 11.4(8) . . . . ?
C21 C23 C24 C25 -175.8(5) . . . . ?
C29 N4 C25 C26 -2.8(8) . . . . ?
C29 N4 C25 C24 175.4(5) . . . . ?
C23 C24 C25 C26 174.1(5) . . . . ?
C23 C24 C25 N4 -4.2(9) . . . . ?
N4 C25 C26 C27 2.9(9) . . . . ?
C24 C25 C26 C27 -175.4(5) . . . . ?
C25 C26 C27 C28 -1.5(11) . . . . ?
C26 C27 C28 C29 0.0(12) . . . . ?
C27 C28 C29 N4 0.1(11) . . . . ?
C25 N4 C29 C28 1.2(9) . . . . ?
C34 N5 C30 C31 0.9(9) . . . . ?
N5 C30 C31 C32 -0.9(11) . . . . ?
C30 C31 C32 C33 0.6(11) . . . . ?
C31 C32 C33 C34 -0.5(10) . . . . ?
C30 N5 C34 C33 -0.8(8) . . . . ?
C30 N5 C34 C35 178.7(5) . . . . ?
C32 C33 C34 N5 0.6(9) . . . . ?
C32 C33 C34 C35 -178.8(6) . . . . ?
N5 C34 C35 C36 178.6(5) . . . . ?
C33 C34 C35 C36 -2.0(9) . . . . ?
C34 C35 C36 C37 -177.8(5) . . . . ?
C35 C36 C37 C38 -172.2(5) . . . . ?
C35 C36 C37 C42 8.7(8) . . . . ?
C42 C37 C38 C39 0.6(7) . . . . ?
C36 C37 C38 C39 -178.6(4) . . . . ?
C37 C38 C39 C40 3.2(7) . . . . ?
C37 C38 C39 C43 -176.6(4) . . . . ?
C38 C39 C40 C41 -4.2(7) . . . . ?
C43 C39 C40 C41 175.5(4) . . . . ?
C38 C39 C40 N7 173.3(4) . . . . ?
C43 C39 C40 N7 -6.9(6) . . . . ?
C44 N7 C40 C41 162.1(4) . . . . ?
C45 N7 C40 C41 -76.6(5) . . . . ?
C44 N7 C40 C39 -15.5(6) . . . . ?
C45 N7 C40 C39 105.8(5) . . . . ?
C39 C40 C41 C42 1.6(7) . . . . ?
N7 C40 C41 C42 -176.0(4) . . . . ?
C40 C41 C42 C37 2.3(7) . . . . ?
C38 C37 C42 C41 -3.3(7) . . . . ?
C36 C37 C42 C41 175.9(5) . . . . ?
C44 N6 C43 C39 43.8(5) . . . . ?
C47 N6 C43 C39 -78.2(5) . . . . ?
C38 C39 C43 N6 171.5(4) . . . . ?
C40 C39 C43 N6 -8.2(6) . . . . ?
C47 N6 C44 N7 52.2(5) . . . . ?
C43 N6 C44 N7 -71.5(5) . . . . ?
C40 N7 C44 N6 55.6(5) . . . . ?
C45 N7 C44 N6 -68.9(5) . . . . ?
C40 N7 C45 C46 -77.3(5) . . . . ?
C44 N7 C45 C46 44.4(5) . . . . ?
N7 C45 C46 C47 -10.1(6) . . . . ?
N7 C45 C46 C51 168.5(4) . . . . ?
C51 C46 C47 C48 -2.0(6) . . . . ?
C45 C46 C47 C48 176.6(4) . . . . ?
C51 C46 C47 N6 175.6(4) . . . . ?
C45 C46 C47 N6 -5.8(6) . . . . ?
C44 N6 C47 C46 -14.5(5) . . . . ?
C43 N6 C47 C46 105.6(4) . . . . ?
C44 N6 C47 C48 163.2(4) . . . . ?
C43 N6 C47 C48 -76.6(5) . . . . ?
C46 C47 C48 C49 1.3(7) . . . . ?
N6 C47 C48 C49 -176.4(4) . . . . ?
C47 C48 C49 C50 0.7(7) . . . . ?
C48 C49 C50 C51 -2.0(7) . . . . ?
C48 C49 C50 C52 179.0(4) . . . . ?
C47 C46 C51 C50 0.7(6) . . . . ?
C45 C46 C51 C50 -177.9(4) . . . . ?
C49 C50 C51 C46 1.2(6) . . . . ?
C52 C50 C51 C46 -179.7(4) . . . . ?
C51 C50 C52 C53 -176.1(5) . . . . ?
C49 C50 C52 C53 3.0(7) . . . . ?
C50 C52 C53 C54 179.7(4) . . . . ?
C58 N8 C54 C55 -3.5(8) . . . . ?
C58 N8 C54 C53 178.3(5) . . . . ?
C52 C53 C54 N8 178.1(5) . . . . ?
C52 C53 C54 C55 -0.1(8) . . . . ?
N8 C54 C55 C56 2.3(8) . . . . ?
C53 C54 C55 C56 -179.6(5) . . . . ?
C54 C55 C56 C57 -0.4(8) . . . . ?
C55 C56 C57 C58 -0.2(9) . . . . ?
C56 C57 C58 N8 -1.2(10) . . . . ?
C54 N8 C58 C57 2.9(10) . . . . ?

_refine_diff_density_max         0.299
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.053



_exptl_crystal_recrystallization_method 'Solvothermal Method'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_tbmp-2
_database_code_depnum_ccdc_archive 'CCDC 2015838'
loop_
_audit_author_name
_audit_author_address
'Jiacheng Zou'
;Tongji University
China
;
_audit_update_record             
;
2020-07-13 deposited with the CCDC.	2021-03-29 downloaded from the CCDC.
;
_audit_creation_date             2019-11-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            TBMP
_chemical_name_systematic        
2,8-bis((E)-2-(pyridin-2-yl)vinyl)-5,6,11,12-tetrahydrodibenzo[b,f][1,5]diazocine
_chemical_formula_moiety         'C29 H24 N4'
_chemical_formula_sum            'C29 H24 N4'
_chemical_formula_weight         428.52
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   19.462(2)
_cell_length_b                   5.2101(4)
_cell_length_c                   26.144(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.318(11)
_cell_angle_gamma                90
_cell_volume                     2556.8(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2104
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      24.9650
_cell_measurement_theta_min      3.0220
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.113
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            7075
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.170
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     36.00  61.00   1.00    5.50    --   11.74 178.00  60.00   25
  2  ω     26.00  80.00   1.00    5.50    --   11.74  37.00 -60.00   54
  3  ω    -61.00  44.00   1.00    5.50    --   11.74 -19.00 150.00  105
  4  ω    -40.00 -14.00   1.00    4.50    --  -11.63  57.00-180.00   26
  5  ω     -7.00  24.00   1.00    4.50    --  -11.63 -99.00-180.00   31
  6  ω     22.00  47.00   1.00    4.50    --   11.66  57.00 -30.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0227574000
_diffrn_orient_matrix_UB_12      -0.0770914000
_diffrn_orient_matrix_UB_13      0.0107938000
_diffrn_orient_matrix_UB_21      0.0246013000
_diffrn_orient_matrix_UB_22      0.0080803000
_diffrn_orient_matrix_UB_23      0.0253650000
_diffrn_orient_matrix_UB_31      -0.0174554000
_diffrn_orient_matrix_UB_32      0.1119018000
_diffrn_orient_matrix_UB_33      0.0056064000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1652
_reflns_number_total             2251
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2251
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0625
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0724P)²+4.1122P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1699
_refine_ls_wR_factor_ref         0.1843
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Fixed Sof: H15A(0.5) H15B(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B)
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C13(H13), C9(H9), C6(H6), C10(H10), C4(H4), C3(H3), C2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N2 N 0.30906(13) 1.3332(4) 0.53034(9) 0.0509(7) Uani 1 1 d . . . . .
C8 C 0.37485(13) 0.7915(5) 0.43098(10) 0.0365(6) Uani 1 1 d . . . . .
C5 C 0.43625(16) 0.1605(5) 0.33283(10) 0.0461(7) Uani 1 1 d . . . . .
H5 H 0.388215 0.158194 0.332072 0.055 Uiso 1 1 calc R U . . .
C12 C 0.28678(14) 1.0995(5) 0.44541(10) 0.0384(6) Uani 1 1 d . . . . .
C7 C 0.39695(15) 0.6041(5) 0.39649(11) 0.0424(7) Uani 1 1 d . . . . .
H7 H 0.361224 0.540869 0.368283 0.051 Uiso 1 1 calc R U . . .
C1 C 0.48201(15) 0.3316(5) 0.36515(10) 0.0415(7) Uani 1 1 d . . . . .
N1 N 0.57876(15) 0.1635(6) 0.33377(11) 0.0705(9) Uani 1 1 d . . . . .
C13 C 0.31088(14) 0.9212(5) 0.41340(11) 0.0402(7) Uani 1 1 d . . . . .
H13 H 0.282766 0.889673 0.379265 0.048 Uiso 1 1 calc R U . . .
C9 C 0.41553(15) 0.8420(5) 0.48277(11) 0.0452(7) Uani 1 1 d . . . . .
H9 H 0.458309 0.755011 0.495854 0.054 Uiso 1 1 calc R U . . .
C14 C 0.21454(16) 1.2176(6) 0.42642(11) 0.0504(8) Uani 1 1 d . . . . .
H14A H 0.215616 1.348014 0.400173 0.060 Uiso 1 1 calc R U . . .
H14B H 0.180662 1.086841 0.409455 0.060 Uiso 1 1 calc R U . . .
C11 C 0.32948(14) 1.1467(5) 0.49594(11) 0.0408(7) Uani 1 1 d . . . . .
C6 C 0.46084(15) 0.5164(5) 0.40095(11) 0.0475(7) Uani 1 1 d . . . . .
H6 H 0.496684 0.576141 0.429479 0.057 Uiso 1 1 calc R U . . .
C10 C 0.39402(15) 1.0157(5) 0.51461(12) 0.0479(7) Uani 1 1 d . . . . .
H10 H 0.422329 1.046775 0.548708 0.057 Uiso 1 1 calc R U . . .
C4 C 0.46225(18) -0.0064(6) 0.30177(11) 0.0532(8) Uani 1 1 d . . . . .
H4 H 0.432120 -0.123424 0.279911 0.064 Uiso 1 1 calc R U . . .
C3 C 0.53207(19) 0.0019(6) 0.30343(12) 0.0575(9) Uani 1 1 d . . . . .
H3 H 0.548741 -0.112164 0.282105 0.069 Uiso 1 1 calc R U . . .
C15 C 0.250000 1.4907(7) 0.500000 0.0527(11) Uani 1 2 d S T P . .
H15A H 0.233123 1.600210 0.524128 0.063 Uiso 0.5 1 calc R U P . .
H15B H 0.266877 1.600200 0.475870 0.063 Uiso 0.5 1 calc R U P . .
C2 C 0.55249(17) 0.3212(7) 0.36439(13) 0.0626(9) Uani 1 1 d . . . . .
H2 H 0.584159 0.431876 0.386794 0.075 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
N2 C14 1.458(3) 2_556 ?
N2 C11 1.449(3) . ?
N2 C15 1.464(3) . ?
C8 C7 1.469(4) . ?
C8 C13 1.384(4) . ?
C8 C9 1.401(4) . ?
C5 H5 0.9300 . ?
C5 C1 1.380(4) . ?
C5 C4 1.374(4) . ?
C12 C13 1.411(4) . ?
C12 C14 1.494(4) . ?
C12 C11 1.384(4) . ?
C7 H7 0.9300 . ?
C7 C6 1.301(4) . ?
C1 C6 1.475(4) . ?
C1 C2 1.378(4) . ?
N1 C3 1.335(4) . ?
N1 C2 1.339(4) . ?
C13 H13 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.368(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C11 C10 1.399(4) . ?
C6 H6 0.9300 . ?
C10 H10 0.9300 . ?
C4 H4 0.9300 . ?
C4 C3 1.349(4) . ?
C3 H3 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C2 H2 0.9300 . ?

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
C14 N2 C15 106.8(2) 2_556 . ?
C11 N2 C14 113.5(2) . 2_556 ?
C11 N2 C15 110.1(2) . . ?
C13 C8 C7 120.3(2) . . ?
C13 C8 C9 117.3(2) . . ?
C9 C8 C7 122.4(2) . . ?
C1 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C4 C5 C1 119.5(3) . . ?
C13 C12 C14 120.3(3) . . ?
C11 C12 C13 118.2(2) . . ?
C11 C12 C14 121.3(2) . . ?
C8 C7 H7 116.3 . . ?
C6 C7 C8 127.3(3) . . ?
C6 C7 H7 116.3 . . ?
C5 C1 C6 124.5(3) . . ?
C2 C1 C5 116.7(3) . . ?
C2 C1 C6 118.7(3) . . ?
C3 N1 C2 115.8(3) . . ?
C8 C13 C12 122.4(3) . . ?
C8 C13 H13 118.8 . . ?
C12 C13 H13 118.8 . . ?
C8 C9 H9 119.1 . . ?
C10 C9 C8 121.8(3) . . ?
C10 C9 H9 119.1 . . ?
N2 C14 C12 112.0(2) 2_556 . ?
N2 C14 H14A 109.2 2_556 . ?
N2 C14 H14B 109.2 2_556 . ?
C12 C14 H14A 109.2 . . ?
C12 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C12 C11 N2 121.2(2) . . ?
C12 C11 C10 120.2(2) . . ?
C10 C11 N2 118.6(3) . . ?
C7 C6 C1 126.4(3) . . ?
C7 C6 H6 116.8 . . ?
C1 C6 H6 116.8 . . ?
C9 C10 C11 120.1(3) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C5 C4 H4 120.5 . . ?
C3 C4 C5 119.1(3) . . ?
C3 C4 H4 120.5 . . ?
N1 C3 C4 124.1(3) . . ?
N1 C3 H3 117.9 . . ?
C4 C3 H3 117.9 . . ?
N2 C15 N2 111.8(3) 2_556 . ?
N2 C15 H15A 109.3 2_556 . ?
N2 C15 H15A 109.3 . . ?
N2 C15 H15B 109.3 2_556 . ?
N2 C15 H15B 109.3 . . ?
H15A C15 H15B 107.9 . . ?
C1 C2 H2 117.6 . . ?
N1 C2 C1 124.8(3) . . ?
N1 C2 H2 117.6 . . ?

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 C11 C10 C9 -178.8(2) . . . . ?
C8 C7 C6 C1 -178.7(2) . . . . ?
C8 C9 C10 C11 0.7(4) . . . . ?
C5 C1 C6 C7 -22.9(4) . . . . ?
C5 C1 C2 N1 1.9(5) . . . . ?
C5 C4 C3 N1 0.1(5) . . . . ?
C12 C11 C10 C9 0.6(4) . . . . ?
C7 C8 C13 C12 178.8(2) . . . . ?
C7 C8 C9 C10 -179.5(2) . . . . ?
C1 C5 C4 C3 -0.3(4) . . . . ?
C13 C8 C7 C6 161.2(3) . . . . ?
C13 C8 C9 C10 -1.3(4) . . . . ?
C13 C12 C14 N2 162.9(2) . . . 2_556 ?
C13 C12 C11 N2 178.1(2) . . . . ?
C13 C12 C11 C10 -1.3(4) . . . . ?
C9 C8 C7 C6 -20.6(4) . . . . ?
C9 C8 C13 C12 0.6(4) . . . . ?
C14 N2 C11 C12 106.8(3) 2_556 . . . ?
C14 N2 C11 C10 -73.8(3) 2_556 . . . ?
C14 N2 C15 N2 -71.52(16) 2_556 . . 2_556 ?
C14 C12 C13 C8 -174.7(2) . . . . ?
C14 C12 C11 N2 -6.6(4) . . . . ?
C14 C12 C11 C10 174.0(2) . . . . ?
C11 N2 C15 N2 52.13(14) . . . 2_556 ?
C11 C12 C13 C8 0.7(4) . . . . ?
C11 C12 C14 N2 -12.3(3) . . . 2_556 ?
C6 C1 C2 N1 -179.8(3) . . . . ?
C4 C5 C1 C6 -178.8(3) . . . . ?
C4 C5 C1 C2 -0.6(4) . . . . ?
C3 N1 C2 C1 -2.1(5) . . . . ?
C15 N2 C11 C12 -12.8(3) . . . . ?
C15 N2 C11 C10 166.6(2) . . . . ?
C2 C1 C6 C7 159.0(3) . . . . ?
C2 N1 C3 C4 1.0(5) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.250 -0.935 0.250 132.8 41.2 ?
2 0.250 -0.390 0.750 132.8 41.2 ?
3 0.750 -0.785 0.250 132.8 41.2 ?
4 0.750 -0.392 0.750 132.8 41.2 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.621
_oxdiff_exptl_absorpt_empirical_full_min 0.609
_exptl_crystal_recrystallization_method 'Solvothermal Method'
####################################################################### 
# 
# 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_tbmp
_database_code_depnum_ccdc_archive 'CCDC 2015839'
loop_
_audit_author_name
_audit_author_address
'Jiacheng Zou'
;Tongji University
China
;
_audit_update_record             
;
2020-07-13 deposited with the CCDC.	2021-03-29 downloaded from the CCDC.
;
_audit_creation_date             2019-11-19
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2019.10.31 svn.r3677 for OlexSys, GUI svn.r5972)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PHZMP
_chemical_name_systematic        
2,8-bis((E)-2-(pyridin-3-yl)vinyl)-5,6,11,12-tetrahydrodibenzo[b,f][1,5]diazocine
_chemical_formula_moiety         'C28 H24 N4'
_chemical_formula_sum            'C28 H24 N4'
_chemical_formula_weight         416.51
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.4388(6)
_cell_length_b                   9.4605(5)
_cell_length_c                   12.5876(8)
_cell_angle_alpha                94.094(5)
_cell_angle_beta                 103.850(5)
_cell_angle_gamma                105.273(5)
_cell_volume                     1041.89(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2766
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.8980
_cell_measurement_theta_min      2.2660
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.03955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Yellow
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_av_unetI/netI     0.0756
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6929
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.255
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -38.00  55.00   1.00    4.00    --  -11.59  57.00 -30.00   93
  2  ω    -84.00  12.00   1.00    4.00    --  -11.59 -57.00-180.00   96
  3  ω    -13.00  78.00   1.00    4.00    --   11.74  77.00  90.00   91
  4  ω    -87.00 -62.00   1.00    5.00    --  -11.59 153.00 165.84   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0068290000
_diffrn_orient_matrix_UB_12      0.0329944000
_diffrn_orient_matrix_UB_13      0.0540839000
_diffrn_orient_matrix_UB_21      0.0772869000
_diffrn_orient_matrix_UB_22      0.0385528000
_diffrn_orient_matrix_UB_23      0.0051784000
_diffrn_orient_matrix_UB_31      -0.0227821000
_diffrn_orient_matrix_UB_32      0.0599379000
_diffrn_orient_matrix_UB_33      -0.0220728000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2605
_reflns_number_total             3636
_reflns_odcompleteness_completeness 98.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         3636
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0625
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0928P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1599
_refine_ls_wR_factor_ref         0.1832
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C21(H21), C18(H18), C5(H5), C2(H2A), C19(H19), C6(H6), C22(H22), C7(H7),
 C13(H13), C27(H27), C25(H25), C10(H10), C26(H26), C12(H12), C11(H11), C28(H28),
  C8(H8), C23(H23)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N3 N 0.6637(2) 0.84054(18) 0.54470(14) 0.0231(5) Uani 1 1 d . . . . .
N2 N 0.4253(2) 0.58507(19) 0.57308(14) 0.0241(5) Uani 1 1 d . . . . .
N1 N 1.0325(2) 0.92465(18) 1.36858(14) 0.0264(5) Uani 1 1 d . . . . .
N4 N 0.1485(2) 0.76875(19) -0.28888(15) 0.0298(5) Uani 1 1 d . . . . .
C4 C 0.5043(2) 0.6360(2) 0.68248(17) 0.0208(5) Uani 1 1 d . . . . .
C20 C 0.3741(2) 0.7684(2) 0.21995(17) 0.0208(5) Uani 1 1 d . . . . .
C21 C 0.3199(2) 0.7174(2) 0.30856(17) 0.0219(5) Uani 1 1 d . . . . .
H21 H 0.216761 0.667677 0.294574 0.026 Uiso 1 1 calc R U . . .
C18 C 0.6236(2) 0.8643(2) 0.35028(17) 0.0216(5) Uani 1 1 d . . . . .
H18 H 0.726642 0.914079 0.363731 0.026 Uiso 1 1 calc R U . . .
C5 C 0.5027(2) 0.5365(2) 0.75987(17) 0.0229(5) Uani 1 1 d . . . . .
H5 H 0.447688 0.437523 0.736511 0.028 Uiso 1 1 calc R U . . .
C17 C 0.5668(2) 0.8142(2) 0.43863(16) 0.0206(5) Uani 1 1 d . . . . .
C2 C 0.6655(2) 0.8285(2) 0.83045(17) 0.0224(5) Uani 1 1 d . . . . .
H2A H 0.719588 0.927629 0.854379 0.027 Uiso 1 1 calc R U . . .
C19 C 0.5306(2) 0.8414(2) 0.24438(17) 0.0224(5) Uani 1 1 d . . . . .
H19 H 0.572315 0.875081 0.187793 0.027 Uiso 1 1 calc R U . . .
C1 C 0.6635(2) 0.7296(2) 0.90905(17) 0.0222(5) Uani 1 1 d . . . . .
C6 C 0.5806(2) 0.5819(2) 0.86966(17) 0.0240(5) Uani 1 1 d . . . . .
H6 H 0.577973 0.512635 0.918580 0.029 Uiso 1 1 calc R U . . .
C3 C 0.5908(2) 0.7851(2) 0.71950(17) 0.0206(5) Uani 1 1 d . . . . .
C14 C 0.6145(2) 0.8947(2) 0.63847(16) 0.0232(5) Uani 1 1 d . . . . .
H14A H 0.519764 0.918329 0.609912 0.028 Uiso 1 1 calc R U . . .
H14B H 0.690450 0.985429 0.677739 0.028 Uiso 1 1 calc R U . . .
C22 C 0.2685(2) 0.7416(2) 0.10962(17) 0.0235(5) Uani 1 1 d . . . . .
H22 H 0.165939 0.700596 0.105325 0.028 Uiso 1 1 calc R U . . .
C7 C 0.7539(2) 0.7798(2) 1.02380(17) 0.0255(5) Uani 1 1 d . . . . .
H7 H 0.790359 0.881553 1.046377 0.031 Uiso 1 1 calc R U . . .
C9 C 0.8755(2) 0.7375(2) 1.21453(18) 0.0242(5) Uani 1 1 d . . . . .
C15 C 0.3383(2) 0.6679(2) 0.50393(17) 0.0241(5) Uani 1 1 d . . . . .
H15A H 0.325568 0.746455 0.551334 0.029 Uiso 1 1 calc R U . . .
H15B H 0.237654 0.602034 0.467351 0.029 Uiso 1 1 calc R U . . .
C24 C 0.1908(2) 0.7433(2) -0.09393(17) 0.0228(5) Uani 1 1 d . . . . .
C16 C 0.4107(2) 0.7364(2) 0.41597(17) 0.0209(5) Uani 1 1 d . . . . .
C13 C 0.9588(2) 0.8835(2) 1.26183(17) 0.0264(5) Uani 1 1 d . . . . .
H13 H 0.962968 0.956190 1.215760 0.032 Uiso 1 1 calc R U . . .
C27 C -0.0628(2) 0.6657(2) -0.21641(17) 0.0268(5) Uani 1 1 d . . . . .
H27 H -0.167337 0.623490 -0.229627 0.032 Uiso 1 1 calc R U . . .
C25 C 0.2397(3) 0.7827(2) -0.18664(17) 0.0260(5) Uani 1 1 d . . . . .
H25 H 0.344054 0.821911 -0.176827 0.031 Uiso 1 1 calc R U . . .
C10 C 0.8757(2) 0.6313(2) 1.28588(18) 0.0257(5) Uani 1 1 d . . . . .
H10 H 0.825001 0.532207 1.258641 0.031 Uiso 1 1 calc R U . . .
C26 C 0.0330(2) 0.6821(2) -0.11192(18) 0.0279(5) Uani 1 1 d . . . . .
H26 H -0.006778 0.652786 -0.053516 0.034 Uiso 1 1 calc R U . . .
C12 C 1.0265(2) 0.8193(2) 1.43479(18) 0.0274(5) Uani 1 1 d . . . . .
H12 H 1.075704 0.846531 1.509756 0.033 Uiso 1 1 calc R U . . .
C11 C 0.9503(2) 0.6723(2) 1.39586(18) 0.0269(5) Uani 1 1 d . . . . .
H11 H 0.949532 0.601733 1.443692 0.032 Uiso 1 1 calc R U . . .
C28 C -0.0011(3) 0.7130(2) -0.30103(18) 0.0289(6) Uani 1 1 d . . . . .
H28 H -0.067224 0.705700 -0.370423 0.035 Uiso 1 1 calc R U . . .
C8 C 0.7889(2) 0.6936(2) 1.09904(18) 0.0279(5) Uani 1 1 d . . . . .
H8 H 0.753413 0.592233 1.074669 0.033 Uiso 1 1 calc R U . . .
C23 C 0.3015(2) 0.7691(2) 0.01414(17) 0.0247(5) Uani 1 1 d . . . . .
H23 H 0.403850 0.807884 0.016695 0.030 Uiso 1 1 calc R U . . .
H3 H 0.758(2) 0.890(2) 0.5517(16) 0.022(6) Uiso 1 1 d . . . . .
H2 H 0.386(2) 0.494(2) 0.5577(18) 0.027(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N3 C17 1.389(2) . ?
N3 C14 1.474(3) . ?
N3 H3 0.87(2) . ?
N2 C4 1.382(2) . ?
N2 C15 1.463(2) . ?
N2 H2 0.83(2) . ?
N1 C13 1.333(3) . ?
N1 C12 1.343(3) . ?
N4 C25 1.342(3) . ?
N4 C28 1.337(3) . ?
C4 C5 1.402(3) . ?
C4 C3 1.411(3) . ?
C20 C21 1.399(3) . ?
C20 C19 1.403(3) . ?
C20 C22 1.463(3) . ?
C21 H21 0.9300 . ?
C21 C16 1.387(3) . ?
C18 H18 0.9300 . ?
C18 C17 1.405(3) . ?
C18 C19 1.376(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.377(3) . ?
C17 C16 1.412(3) . ?
C2 H2A 0.9300 . ?
C2 C1 1.409(3) . ?
C2 C3 1.382(3) . ?
C19 H19 0.9300 . ?
C1 C6 1.397(3) . ?
C1 C7 1.462(3) . ?
C6 H6 0.9300 . ?
C3 C14 1.518(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C22 H22 0.9300 . ?
C22 C23 1.338(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.332(3) . ?
C9 C13 1.402(3) . ?
C9 C10 1.395(3) . ?
C9 C8 1.456(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.531(3) . ?
C24 C25 1.394(3) . ?
C24 C26 1.404(3) . ?
C24 C23 1.463(3) . ?
C13 H13 0.9300 . ?
C27 H27 0.9300 . ?
C27 C26 1.378(3) . ?
C27 C28 1.379(3) . ?
C25 H25 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11 1.369(3) . ?
C26 H26 0.9300 . ?
C12 H12 0.9300 . ?
C12 C11 1.378(3) . ?
C11 H11 0.9300 . ?
C28 H28 0.9300 . ?
C8 H8 0.9300 . ?
C23 H23 0.9300 . ?

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
C17 N3 C14 119.46(18) . . ?
C17 N3 H3 115.8(13) . . ?
C14 N3 H3 108.8(14) . . ?
C4 N2 C15 123.12(18) . . ?
C4 N2 H2 115.5(14) . . ?
C15 N2 H2 112.9(15) . . ?
C13 N1 C12 117.72(17) . . ?
C28 N4 C25 116.39(18) . . ?
N2 C4 C5 119.50(17) . . ?
N2 C4 C3 122.33(17) . . ?
C5 C4 C3 118.16(18) . . ?
C21 C20 C19 116.16(18) . . ?
C21 C20 C22 119.57(18) . . ?
C19 C20 C22 124.26(18) . . ?
C20 C21 H21 118.0 . . ?
C16 C21 C20 124.01(19) . . ?
C16 C21 H21 118.0 . . ?
C17 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
C19 C18 C17 121.65(19) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 C4 121.62(18) . . ?
C6 C5 H5 119.2 . . ?
N3 C17 C18 120.13(18) . . ?
N3 C17 C16 121.65(18) . . ?
C18 C17 C16 118.21(18) . . ?
C1 C2 H2A 118.4 . . ?
C3 C2 H2A 118.4 . . ?
C3 C2 C1 123.12(18) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 C20 121.41(19) . . ?
C18 C19 H19 119.3 . . ?
C2 C1 C7 120.60(18) . . ?
C6 C1 C2 116.58(19) . . ?
C6 C1 C7 122.67(18) . . ?
C5 C6 C1 121.36(18) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
C4 C3 C14 121.10(18) . . ?
C2 C3 C4 119.12(17) . . ?
C2 C3 C14 119.56(16) . . ?
N3 C14 C3 113.89(16) . . ?
N3 C14 H14A 108.8 . . ?
N3 C14 H14B 108.8 . . ?
C3 C14 H14A 108.8 . . ?
C3 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C20 C22 H22 116.0 . . ?
C23 C22 C20 127.9(2) . . ?
C23 C22 H22 116.0 . . ?
C1 C7 H7 116.9 . . ?
C8 C7 C1 126.1(2) . . ?
C8 C7 H7 116.9 . . ?
C13 C9 C8 124.21(18) . . ?
C10 C9 C13 116.0(2) . . ?
C10 C9 C8 119.73(18) . . ?
N2 C15 H15A 108.6 . . ?
N2 C15 H15B 108.6 . . ?
N2 C15 C16 114.75(17) . . ?
H15A C15 H15B 107.6 . . ?
C16 C15 H15A 108.6 . . ?
C16 C15 H15B 108.6 . . ?
C25 C24 C26 115.94(19) . . ?
C25 C24 C23 120.02(19) . . ?
C26 C24 C23 124.03(19) . . ?
C21 C16 C17 118.51(18) . . ?
C21 C16 C15 118.60(17) . . ?
C17 C16 C15 122.86(17) . . ?
N1 C13 C9 124.19(18) . . ?
N1 C13 H13 117.9 . . ?
C9 C13 H13 117.9 . . ?
C26 C27 H27 120.6 . . ?
C26 C27 C28 118.9(2) . . ?
C28 C27 H27 120.6 . . ?
N4 C25 C24 125.3(2) . . ?
N4 C25 H25 117.4 . . ?
C24 C25 H25 117.4 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.31(19) . . ?
C11 C10 H10 119.8 . . ?
C24 C26 H26 120.1 . . ?
C27 C26 C24 119.79(19) . . ?
C27 C26 H26 120.1 . . ?
N1 C12 H12 118.8 . . ?
N1 C12 C11 122.5(2) . . ?
C11 C12 H12 118.8 . . ?
C10 C11 C12 119.20(18) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
N4 C28 C27 123.7(2) . . ?
N4 C28 H28 118.2 . . ?
C27 C28 H28 118.2 . . ?
C7 C8 C9 128.3(2) . . ?
C7 C8 H8 115.8 . . ?
C9 C8 H8 115.8 . . ?
C22 C23 C24 125.7(2) . . ?
C22 C23 H23 117.1 . . ?
C24 C23 H23 117.1 . . ?

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
N3 C17 C16 C21 178.40(17) . . . . ?
N3 C17 C16 C15 -3.6(3) . . . . ?
N2 C4 C5 C6 179.54(19) . . . . ?
N2 C4 C3 C2 179.23(19) . . . . ?
N2 C4 C3 C14 -6.2(3) . . . . ?
N2 C15 C16 C21 132.39(19) . . . . ?
N2 C15 C16 C17 -45.6(3) . . . . ?
N1 C12 C11 C10 -0.9(4) . . . . ?
C4 N2 C15 C16 107.6(2) . . . . ?
C4 C5 C6 C1 0.7(3) . . . . ?
C4 C3 C14 N3 -48.6(3) . . . . ?
C20 C21 C16 C17 1.2(3) . . . . ?
C20 C21 C16 C15 -176.86(18) . . . . ?
C20 C22 C23 C24 -178.48(18) . . . . ?
C21 C20 C19 C18 -1.6(3) . . . . ?
C21 C20 C22 C23 -173.0(2) . . . . ?
C18 C17 C16 C21 -2.1(3) . . . . ?
C18 C17 C16 C15 175.90(17) . . . . ?
C5 C4 C3 C2 -2.4(3) . . . . ?
C5 C4 C3 C14 172.15(19) . . . . ?
C17 N3 C14 C3 113.65(19) . . . . ?
C17 C18 C19 C20 0.7(3) . . . . ?
C2 C1 C6 C5 -1.2(3) . . . . ?
C2 C1 C7 C8 -164.1(2) . . . . ?
C2 C3 C14 N3 125.9(2) . . . . ?
C19 C20 C21 C16 0.6(3) . . . . ?
C19 C20 C22 C23 6.0(3) . . . . ?
C19 C18 C17 N3 -179.31(17) . . . . ?
C19 C18 C17 C16 1.2(3) . . . . ?
C1 C2 C3 C4 2.0(3) . . . . ?
C1 C2 C3 C14 -172.7(2) . . . . ?
C1 C7 C8 C9 -178.6(2) . . . . ?
C6 C1 C7 C8 11.2(4) . . . . ?
C3 C4 C5 C6 1.1(3) . . . . ?
C3 C2 C1 C6 -0.1(3) . . . . ?
C3 C2 C1 C7 175.42(19) . . . . ?
C14 N3 C17 C18 134.63(19) . . . . ?
C14 N3 C17 C16 -45.9(2) . . . . ?
C22 C20 C21 C16 179.66(17) . . . . ?
C22 C20 C19 C18 179.41(17) . . . . ?
C7 C1 C6 C5 -176.7(2) . . . . ?
C9 C10 C11 C12 -0.8(3) . . . . ?
C15 N2 C4 C5 140.1(2) . . . . ?
C15 N2 C4 C3 -41.6(3) . . . . ?
C13 N1 C12 C11 1.2(3) . . . . ?
C13 C9 C10 C11 2.0(3) . . . . ?
C13 C9 C8 C7 -10.8(4) . . . . ?
C25 N4 C28 C27 -2.5(3) . . . . ?
C25 C24 C26 C27 -0.5(3) . . . . ?
C25 C24 C23 C22 177.19(19) . . . . ?
C10 C9 C13 N1 -1.7(3) . . . . ?
C10 C9 C8 C7 167.7(2) . . . . ?
C26 C24 C25 N4 1.1(3) . . . . ?
C26 C24 C23 C22 -1.6(3) . . . . ?
C26 C27 C28 N4 3.0(3) . . . . ?
C12 N1 C13 C9 0.1(3) . . . . ?
C28 N4 C25 C24 0.4(3) . . . . ?
C28 C27 C26 C24 -1.3(3) . . . . ?
C8 C9 C13 N1 176.9(2) . . . . ?
C8 C9 C10 C11 -176.7(2) . . . . ?
C23 C24 C25 N4 -177.78(18) . . . . ?
C23 C24 C26 C27 178.26(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 15.290
_oxdiff_exptl_absorpt_empirical_full_min 0.444
_exptl_crystal_recrystallization_method 'Solvothermal Method'
####################################################################### 
# 
# 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_tbop_2
_database_code_depnum_ccdc_archive 'CCDC 2015836'
loop_
_audit_author_name
_audit_author_address
'Jiacheng Zou'
;Tongji University
China
;
_audit_update_record             
;
2020-07-13 deposited with the CCDC.	2021-03-29 downloaded from the CCDC.
;
_audit_creation_date             2020-05-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PHZOP
_chemical_name_systematic        
2,8-bis((E)-2-(pyridin-2-yl)vinyl)-5,6,11,12-tetrahydrodibenzo[b,f][1,5]diazocine
_chemical_formula_moiety         'C28 H24 N4'
_chemical_formula_sum            'C28 H24 N4'
_chemical_formula_weight         416.51
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
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'

_cell_length_a                   4.8535(6)
_cell_length_b                   37.442(5)
_cell_length_c                   11.8808(10)
_cell_angle_alpha                90
_cell_angle_beta                 101.043(10)
_cell_angle_gamma                90
_cell_volume                     2119.0(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2089
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.5170
_cell_measurement_theta_min      4.4450
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.609
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.25907
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Yellow
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0761
_diffrn_reflns_av_unetI/netI     0.0823
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5546
_diffrn_reflns_point_group_measured_fraction_full 0.716
_diffrn_reflns_point_group_measured_fraction_max 0.693
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.663
_diffrn_reflns_theta_min         2.360
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00  33.00   1.00    1.50    --  -40.98  37.00 -90.00   98
  2  ω    -67.00  32.00   1.00    1.50    --  -40.98  57.00 120.00   99
  3  ω     56.00  93.00   1.00    1.50    --   40.98-125.00 -90.00   37
  4  ω     27.00  54.00   1.00    1.50    --   40.98-125.00-180.00   27
  5  ω    107.00 135.00   1.00    2.50    --  106.95 -61.00 -60.00   28
  6  ω     83.00 118.00   1.00    2.50    --  106.95-125.00  30.00   35
  7  ω     65.00 117.00   1.00    2.50    --  106.95 -30.00  30.00   52
  8  ω     89.00 178.00   1.00    2.50    --  106.95  45.00  90.00   89
  9  ω    105.00 162.00   1.00    2.50    --  106.95 125.00  30.00   57
 10  ω     79.00 123.00   1.00    2.50    --  106.95  61.00-180.00   44
 11  ω    145.00 172.00   1.00    2.50    --  106.95  61.00-180.00   27
 12  ω     54.00 167.00   1.00    2.50    --  106.95   0.00-120.00  113
 13  ω     42.00 121.00   1.00    2.50    --  106.95-125.00 -90.00   79
 14  ω     42.00  69.00   1.00    2.50    --  106.95-125.00  30.00   27
 15  ω     32.00 136.00   1.00    2.50    --  106.95 -77.00  90.00  104
 16  ω     38.00  49.00   1.00    2.50    --  106.95 -94.00 -60.00   11
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0694440000
_diffrn_orient_matrix_UB_12      -0.0368978000
_diffrn_orient_matrix_UB_13      -0.0449852000
_diffrn_orient_matrix_UB_21      0.2134404000
_diffrn_orient_matrix_UB_22      -0.0065584000
_diffrn_orient_matrix_UB_23      0.1119898000
_diffrn_orient_matrix_UB_31      -0.2330370000
_diffrn_orient_matrix_UB_32      -0.0169851000
_diffrn_orient_matrix_UB_33      0.0539162000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.420
_reflns_Friedel_fraction_full    0.438
_reflns_Friedel_fraction_max     0.412
_reflns_number_gt                2531
_reflns_number_total             2947
_reflns_odcompleteness_completeness 99.02
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details 
;
 Flack x determined using 546 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         2947
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0719
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1316P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1877
_refine_ls_wR_factor_ref         0.2040
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3A), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C13(H13),
 C17(H17), C19(H19), C20(H20), C22(H22), C23(H23), C25(H25), C26(H26), C27(H27),
  C28(H28), N2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7345(12) 0.73243(16) 0.4254(5) 0.0364(12) Uani 1 1 d . . . . .
C2 C 0.6947(14) 0.74631(18) 0.3141(5) 0.0436(14) Uani 1 1 d . . . . .
H2A H 0.552572 0.737575 0.256939 0.052 Uiso 1 1 calc R U . . .
C3 C 0.8704(17) 0.77329(18) 0.2907(6) 0.0514(16) Uani 1 1 d . . . . .
H3A H 0.845174 0.783361 0.217852 0.062 Uiso 1 1 calc R U . . .
C4 C 1.0824(14) 0.78498(19) 0.3764(7) 0.0505(16) Uani 1 1 d . . . . .
H4 H 1.206639 0.802576 0.362277 0.061 Uiso 1 1 calc R U . . .
C5 C 1.1071(13) 0.76978(16) 0.4855(6) 0.0433(14) Uani 1 1 d . . . . .
H5 H 1.247687 0.778123 0.544006 0.052 Uiso 1 1 calc R U . . .
C6 C 0.5537(12) 0.70328(15) 0.4508(5) 0.0333(11) Uani 1 1 d . . . . .
H6 H 0.400928 0.696900 0.394458 0.040 Uiso 1 1 calc R U . . .
C7 C 0.5948(10) 0.68536(14) 0.5497(4) 0.0268(10) Uani 1 1 d . . . . .
H7 H 0.743385 0.692984 0.606016 0.032 Uiso 1 1 calc R U . . .
C8 C 0.4330(10) 0.65518(13) 0.5793(4) 0.0258(10) Uani 1 1 d . . . . .
C9 C 0.5261(11) 0.63646(14) 0.6808(4) 0.0278(10) Uani 1 1 d . . . . .
H9 H 0.683309 0.644668 0.731589 0.033 Uiso 1 1 calc R U . . .
C10 C 0.3925(10) 0.60621(14) 0.7080(4) 0.0258(10) Uani 1 1 d . . . . .
H10 H 0.460135 0.594539 0.776824 0.031 Uiso 1 1 calc R U . . .
C11 C 0.1538(9) 0.59250(13) 0.6332(4) 0.0215(9) Uani 1 1 d . . . . .
C12 C 0.0495(10) 0.61185(13) 0.5325(4) 0.0238(10) Uani 1 1 d . . . . .
C13 C 0.1860(10) 0.64233(13) 0.5073(4) 0.0240(9) Uani 1 1 d . . . . .
H13 H 0.113133 0.654887 0.440739 0.029 Uiso 1 1 calc R U . . .
C14 C -0.2059(10) 0.59956(13) 0.4455(4) 0.0239(10) Uani 1 1 d . . . . .
H14A H -0.367(13) 0.5882(17) 0.485(5) 0.027(15) Uiso 1 1 d . . . . .
H14B H -0.276(14) 0.6195(19) 0.396(6) 0.036(17) Uiso 1 1 d . . . . .
C15 C -0.0958(10) 0.53419(14) 0.5823(4) 0.0253(10) Uani 1 1 d . . . . .
H15A H -0.312(10) 0.5402(12) 0.540(4) 0.002(10) Uiso 1 1 d . . . . .
H15B H -0.106(19) 0.513(2) 0.644(8) 0.07(3) Uiso 1 1 d . . . . .
C16 C 0.0710(9) 0.52566(13) 0.4908(4) 0.0217(9) Uani 1 1 d . . . . .
C17 C 0.2495(9) 0.49636(13) 0.5066(4) 0.0218(9) Uani 1 1 d . . . . .
H17 H 0.260019 0.482852 0.573016 0.026 Uiso 1 1 calc R U . . .
C18 C 0.4170(9) 0.48600(13) 0.4262(4) 0.0232(9) Uani 1 1 d . . . . .
C19 C 0.3928(10) 0.50708(14) 0.3274(4) 0.0255(10) Uani 1 1 d . . . . .
H19 H 0.501622 0.501622 0.273267 0.031 Uiso 1 1 calc R U . . .
C20 C 0.2123(10) 0.53561(14) 0.3087(4) 0.0246(10) Uani 1 1 d . . . . .
H20 H 0.197851 0.548473 0.240819 0.029 Uiso 1 1 calc R U . . .
C21 C 0.0472(9) 0.54609(13) 0.3893(3) 0.0202(9) Uani 1 1 d . . . . .
C22 C 0.6151(10) 0.45654(14) 0.4424(4) 0.0264(10) Uani 1 1 d . . . . .
H22 H 0.720291 0.453441 0.385469 0.032 Uiso 1 1 calc R U . . .
C23 C 0.6646(10) 0.43325(13) 0.5298(4) 0.0265(10) Uani 1 1 d . . . . .
H23 H 0.566144 0.436507 0.588872 0.032 Uiso 1 1 calc R U . . .
C24 C 0.8605(11) 0.40312(14) 0.5401(4) 0.0293(11) Uani 1 1 d . . . . .
C25 C 0.9923(11) 0.39175(15) 0.4506(4) 0.0300(11) Uani 1 1 d . . . . .
H25 H 0.964711 0.404153 0.381549 0.036 Uiso 1 1 calc R U . . .
C26 C 1.1626(12) 0.36203(16) 0.4665(5) 0.0366(12) Uani 1 1 d . . . . .
H26 H 1.247149 0.353835 0.407483 0.044 Uiso 1 1 calc R U . . .
C27 C 1.2075(17) 0.34431(19) 0.5716(5) 0.0512(17) Uani 1 1 d . . . . .
H27 H 1.323127 0.324346 0.584939 0.061 Uiso 1 1 calc R U . . .
C28 C 1.0757(19) 0.3574(2) 0.6535(6) 0.060(2) Uani 1 1 d . . . . .
H28 H 1.104137 0.345618 0.723788 0.072 Uiso 1 1 calc R U . . .
N1 N 0.9373(10) 0.74371(14) 0.5097(4) 0.0371(11) Uani 1 1 d . . . . .
N2 N -0.1332(8) 0.57424(12) 0.3611(3) 0.0252(9) Uani 1 1 d . . . . .
H2 H -0.208105 0.577277 0.290077 0.030 Uiso 1 1 calc R U . . .
N3 N 0.0327(8) 0.56142(11) 0.6666(3) 0.0250(9) Uani 1 1 d . . . . .
H3 H 0.163(12) 0.5543(16) 0.740(5) 0.023(13) Uiso 1 1 d . . . . .
N4 N 0.9065(13) 0.38612(15) 0.6404(4) 0.0442(13) 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 C2 1.399(8) . ?
C1 C6 1.468(8) . ?
C1 N1 1.332(8) . ?
C2 H2A 0.9300 . ?
C2 C3 1.384(9) . ?
C3 H3A 0.9300 . ?
C3 C4 1.373(11) . ?
C4 H4 0.9300 . ?
C4 C5 1.400(10) . ?
C5 H5 0.9300 . ?
C5 N1 1.344(8) . ?
C6 H6 0.9300 . ?
C6 C7 1.334(7) . ?
C7 H7 0.9300 . ?
C7 C8 1.457(7) . ?
C8 C9 1.393(7) . ?
C8 C13 1.417(7) . ?
C9 H9 0.9300 . ?
C9 C10 1.374(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.414(7) . ?
C11 C12 1.407(7) . ?
C11 N3 1.396(6) . ?
C12 C13 1.381(7) . ?
C12 C14 1.525(6) . ?
C13 H13 0.9300 . ?
C14 H14A 1.08(7) . ?
C14 H14B 0.97(7) . ?
C14 N2 1.471(6) . ?
C15 H15A 1.10(5) . ?
C15 H15B 1.10(9) . ?
C15 C16 1.508(6) . ?
C15 N3 1.481(6) . ?
C16 C17 1.388(7) . ?
C16 C21 1.414(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.422(6) . ?
C18 C19 1.400(7) . ?
C18 C22 1.452(7) . ?
C19 H19 0.9300 . ?
C19 C20 1.372(7) . ?
C20 H20 0.9300 . ?
C20 C21 1.417(6) . ?
C21 N2 1.370(6) . ?
C22 H22 0.9300 . ?
C22 C23 1.341(7) . ?
C23 H23 0.9300 . ?
C23 C24 1.465(7) . ?
C24 C25 1.408(7) . ?
C24 N4 1.331(7) . ?
C25 H25 0.9300 . ?
C25 C26 1.377(8) . ?
C26 H26 0.9300 . ?
C26 C27 1.394(8) . ?
C27 H27 0.9300 . ?
C27 C28 1.354(9) . ?
C28 H28 0.9300 . ?
C28 N4 1.345(8) . ?
N2 H2 0.8600 . ?
N3 H3 1.01(6) . ?

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 C1 C6 119.4(5) . . ?
N1 C1 C2 122.8(6) . . ?
N1 C1 C6 117.8(5) . . ?
C1 C2 H2A 120.6 . . ?
C3 C2 C1 118.8(6) . . ?
C3 C2 H2A 120.6 . . ?
C2 C3 H3A 120.5 . . ?
C4 C3 C2 119.1(6) . . ?
C4 C3 H3A 120.5 . . ?
C3 C4 H4 120.8 . . ?
C3 C4 C5 118.5(6) . . ?
C5 C4 H4 120.8 . . ?
C4 C5 H5 118.4 . . ?
N1 C5 C4 123.1(6) . . ?
N1 C5 H5 118.4 . . ?
C1 C6 H6 117.9 . . ?
C7 C6 C1 124.1(5) . . ?
C7 C6 H6 117.9 . . ?
C6 C7 H7 116.3 . . ?
C6 C7 C8 127.3(5) . . ?
C8 C7 H7 116.3 . . ?
C9 C8 C7 119.9(4) . . ?
C9 C8 C13 116.6(4) . . ?
C13 C8 C7 123.4(4) . . ?
C8 C9 H9 119.0 . . ?
C10 C9 C8 121.9(5) . . ?
C10 C9 H9 119.0 . . ?
C9 C10 H10 119.4 . . ?
C9 C10 C11 121.2(5) . . ?
C11 C10 H10 119.4 . . ?
C12 C11 C10 117.7(4) . . ?
N3 C11 C10 117.5(4) . . ?
N3 C11 C12 124.7(4) . . ?
C11 C12 C14 122.3(4) . . ?
C13 C12 C11 120.0(4) . . ?
C13 C12 C14 117.7(4) . . ?
C8 C13 H13 118.8 . . ?
C12 C13 C8 122.4(4) . . ?
C12 C13 H13 118.8 . . ?
C12 C14 H14A 113(3) . . ?
C12 C14 H14B 109(4) . . ?
H14A C14 H14B 112(5) . . ?
N2 C14 C12 112.7(4) . . ?
N2 C14 H14A 109(3) . . ?
N2 C14 H14B 101(4) . . ?
H15A C15 H15B 107(5) . . ?
C16 C15 H15A 108(2) . . ?
C16 C15 H15B 115(5) . . ?
N3 C15 H15A 114(2) . . ?
N3 C15 H15B 97(5) . . ?
N3 C15 C16 114.8(4) . . ?
C17 C16 C15 118.5(4) . . ?
C17 C16 C21 119.3(4) . . ?
C21 C16 C15 122.2(4) . . ?
C16 C17 H17 118.4 . . ?
C16 C17 C18 123.1(4) . . ?
C18 C17 H17 118.4 . . ?
C17 C18 C22 124.5(4) . . ?
C19 C18 C17 116.3(4) . . ?
C19 C18 C22 119.1(4) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 C18 121.6(4) . . ?
C20 C19 H19 119.2 . . ?
C19 C20 H20 118.9 . . ?
C19 C20 C21 122.1(4) . . ?
C21 C20 H20 118.9 . . ?
C16 C21 C20 117.6(4) . . ?
N2 C21 C16 124.6(4) . . ?
N2 C21 C20 117.7(4) . . ?
C18 C22 H22 116.1 . . ?
C23 C22 C18 127.8(4) . . ?
C23 C22 H22 116.1 . . ?
C22 C23 H23 117.2 . . ?
C22 C23 C24 125.6(5) . . ?
C24 C23 H23 117.2 . . ?
C25 C24 C23 123.5(5) . . ?
N4 C24 C23 116.0(5) . . ?
N4 C24 C25 120.6(5) . . ?
C24 C25 H25 120.4 . . ?
C26 C25 C24 119.2(5) . . ?
C26 C25 H25 120.4 . . ?
C25 C26 H26 120.2 . . ?
C25 C26 C27 119.6(5) . . ?
C27 C26 H26 120.2 . . ?
C26 C27 H27 121.4 . . ?
C28 C27 C26 117.3(6) . . ?
C28 C27 H27 121.4 . . ?
C27 C28 H28 117.7 . . ?
N4 C28 C27 124.6(6) . . ?
N4 C28 H28 117.7 . . ?
C1 N1 C5 117.7(5) . . ?
C14 N2 H2 118.2 . . ?
C21 N2 C14 123.7(4) . . ?
C21 N2 H2 118.2 . . ?
C11 N3 C15 121.8(4) . . ?
C11 N3 H3 104(3) . . ?
C15 N3 H3 121(3) . . ?
C24 N4 C28 118.7(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
C1 C2 C3 C4 1.6(10) . . . . ?
C1 C6 C7 C8 -177.0(5) . . . . ?
C2 C1 C6 C7 171.7(6) . . . . ?
C2 C1 N1 C5 0.6(9) . . . . ?
C2 C3 C4 C5 -1.9(11) . . . . ?
C3 C4 C5 N1 1.6(10) . . . . ?
C4 C5 N1 C1 -1.0(9) . . . . ?
C6 C1 C2 C3 -178.7(6) . . . . ?
C6 C1 N1 C5 178.3(5) . . . . ?
C6 C7 C8 C9 171.5(5) . . . . ?
C6 C7 C8 C13 -5.8(8) . . . . ?
C7 C8 C9 C10 -174.9(4) . . . . ?
C7 C8 C13 C12 174.3(4) . . . . ?
C8 C9 C10 C11 0.5(7) . . . . ?
C9 C8 C13 C12 -3.1(7) . . . . ?
C9 C10 C11 C12 -3.0(7) . . . . ?
C9 C10 C11 N3 179.2(4) . . . . ?
C10 C11 C12 C13 2.5(6) . . . . ?
C10 C11 C12 C14 179.8(4) . . . . ?
C10 C11 N3 C15 -145.3(4) . . . . ?
C11 C12 C13 C8 0.5(7) . . . . ?
C11 C12 C14 N2 -86.1(5) . . . . ?
C12 C11 N3 C15 37.2(7) . . . . ?
C12 C14 N2 C21 44.6(6) . . . . ?
C13 C8 C9 C10 2.5(7) . . . . ?
C13 C12 C14 N2 91.3(5) . . . . ?
C14 C12 C13 C8 -176.9(4) . . . . ?
C15 C16 C17 C18 -179.7(4) . . . . ?
C15 C16 C21 C20 -179.6(4) . . . . ?
C15 C16 C21 N2 -2.8(7) . . . . ?
C16 C15 N3 C11 43.2(6) . . . . ?
C16 C17 C18 C19 -0.3(7) . . . . ?
C16 C17 C18 C22 177.1(4) . . . . ?
C16 C21 N2 C14 35.6(7) . . . . ?
C17 C16 C21 C20 -0.8(6) . . . . ?
C17 C16 C21 N2 176.1(4) . . . . ?
C17 C18 C19 C20 -1.4(7) . . . . ?
C17 C18 C22 C23 3.8(8) . . . . ?
C18 C19 C20 C21 2.1(7) . . . . ?
C18 C22 C23 C24 177.7(5) . . . . ?
C19 C18 C22 C23 -178.9(5) . . . . ?
C19 C20 C21 C16 -0.9(7) . . . . ?
C19 C20 C21 N2 -178.0(4) . . . . ?
C20 C21 N2 C14 -147.6(4) . . . . ?
C21 C16 C17 C18 1.4(7) . . . . ?
C22 C18 C19 C20 -178.9(4) . . . . ?
C22 C23 C24 C25 -9.6(8) . . . . ?
C22 C23 C24 N4 171.4(5) . . . . ?
C23 C24 C25 C26 -176.8(5) . . . . ?
C23 C24 N4 C28 177.4(6) . . . . ?
C24 C25 C26 C27 -1.7(9) . . . . ?
C25 C24 N4 C28 -1.6(10) . . . . ?
C25 C26 C27 C28 0.7(11) . . . . ?
C26 C27 C28 N4 -0.2(14) . . . . ?
C27 C28 N4 C24 0.7(13) . . . . ?
N1 C1 C2 C3 -1.0(10) . . . . ?
N1 C1 C6 C7 -6.1(8) . . . . ?
N3 C11 C12 C13 -179.9(4) . . . . ?
N3 C11 C12 C14 -2.6(7) . . . . ?
N3 C15 C16 C17 95.9(5) . . . . ?
N3 C15 C16 C21 -85.3(5) . . . . ?
N4 C24 C25 C26 2.2(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.543
_oxdiff_exptl_absorpt_empirical_full_min 0.173
_exptl_crystal_recrystallization_method 'Solvothermal Method'
