# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2022

####################################################################### 
# 
# 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_E-2NH2-TPE
_database_code_depnum_ccdc_archive 'CCDC 2120059'
loop_
_audit_author_name
_audit_author_address
lx
;Sichuan University
China
;
_audit_update_record             
;
2021-11-03 deposited with the CCDC.	2022-01-04 downloaded from the CCDC.
;
_audit_creation_date             2020-12-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C26 H22 N2'
_chemical_formula_sum            'C26 H22 N2'
_chemical_formula_weight         362.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3
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                   6.1471(3)
_cell_length_b                   17.7972(9)
_cell_length_c                   20.5612(10)
_cell_angle_alpha                76.086(4)
_cell_angle_beta                 81.665(4)
_cell_angle_gamma                86.606(4)
_cell_volume                     2159.65(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3244
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.9190
_cell_measurement_theta_min      3.3910
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98649
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.115
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            17610
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         3.038
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -80.00  -53.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      -15.4773 -178.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega  -20.00   20.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      -15.4773  -99.0000  150.0000 40

#__ type_ start__ end____ width___ exp.time_
  3 omega  -11.00   23.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      -15.4773  -99.0000  -90.0000 34

#__ type_ start__ end____ width___ exp.time_
  4 omega  -65.00   -8.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      -15.4773  -57.0000   60.0000 57

#__ type_ start__ end____ width___ exp.time_
  5 omega  -37.00   34.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -       17.5086  -57.0000    0.0000 71

#__ type_ start__ end____ width___ exp.time_
  6 omega  -52.00   31.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -       17.5086  -38.0000  120.0000 83

#__ type_ start__ end____ width___ exp.time_
  7 omega  -50.00   34.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -       17.5086  -57.0000 -120.0000 84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0063937000
_diffrn_orient_matrix_UB_12      0.0238840000
_diffrn_orient_matrix_UB_13      0.0227136000
_diffrn_orient_matrix_UB_21      -0.0142830000
_diffrn_orient_matrix_UB_22      0.0333684000
_diffrn_orient_matrix_UB_23      -0.0261312000
_diffrn_orient_matrix_UB_31      -0.1156028000
_diffrn_orient_matrix_UB_32      -0.0017509000
_diffrn_orient_matrix_UB_33      0.0093677000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4842
_reflns_number_total             8811
_reflns_odcompleteness_completeness 99.86
_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, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     512
_refine_ls_number_reflns         8811
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1065
_refine_ls_R_factor_gt           0.0546
_refine_ls_restrained_S_all      0.998
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0593P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1389
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
2.a Rotating group:
 N2(H2A,H2B), N3(H3A,H3B), N4(H4A)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C16(H16), C17(H17), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24),
  C25(H25), C26(H26), C30(H30), C31(H31), C33(H33), C34(H34), C36(H36),
 C37(H37), C38(H38), C39(H39), C40(H40), C42(H42), C43(H43), C45(H45), C46(H46),
  C48(H48), C49(H49), C50(H50), C51(H51), C52(H52)
2.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 1.1845(3) 0.82135(11) 0.54061(9) 0.0811(6) Uani 1 1 d . . . . .
H1A H 1.3123 0.8015 0.5477 0.097 Uiso 1 1 calc R . . . .
H1B H 1.1158 0.8486 0.5668 0.097 Uiso 1 1 calc R . . . .
N2 N 0.5788(4) 0.69193(14) 0.03921(10) 0.1124(8) Uani 1 1 d . . . . .
H2A H 0.4538 0.6694 0.0438 0.135 Uiso 1 1 d GR . . . .
H2B H 0.5685 0.7375 0.0124 0.135 Uiso 1 1 d GR . . . .
C1 C 0.8102(3) 0.78677(11) 0.31200(9) 0.0504(5) Uani 1 1 d . . . . .
C2 C 0.7949(3) 0.71994(11) 0.29305(9) 0.0490(5) Uani 1 1 d . . . . .
C3 C 0.9036(3) 0.79103(10) 0.37409(9) 0.0475(5) Uani 1 1 d . . . . .
C4 C 0.7999(3) 0.83520(11) 0.41698(10) 0.0574(5) Uani 1 1 d . . . . .
H4 H 0.6660 0.8598 0.4081 0.069 Uiso 1 1 calc R . . . .
C5 C 0.8882(3) 0.84392(11) 0.47226(10) 0.0604(5) Uani 1 1 d . . . . .
H5 H 0.8120 0.8733 0.5004 0.072 Uiso 1 1 calc R . . . .
C6 C 1.0891(3) 0.80950(11) 0.48675(10) 0.0539(5) Uani 1 1 d . . . . .
C7 C 1.1952(3) 0.76617(11) 0.44386(10) 0.0586(5) Uani 1 1 d . . . . .
H7 H 1.3308 0.7427 0.4522 0.070 Uiso 1 1 calc R . . . .
C8 C 1.1050(3) 0.75685(11) 0.38904(10) 0.0549(5) Uani 1 1 d . . . . .
H8 H 1.1806 0.7269 0.3613 0.066 Uiso 1 1 calc R . . . .
C9 C 0.7443(3) 0.86399(11) 0.27068(10) 0.0555(5) Uani 1 1 d . . . . .
C10 C 0.8851(4) 0.92480(13) 0.25652(12) 0.0757(6) Uani 1 1 d . . . . .
H10 H 1.0195 0.9170 0.2732 0.091 Uiso 1 1 calc R . . . .
C11 C 0.8342(6) 0.99611(15) 0.21883(14) 0.0997(8) Uani 1 1 d . . . . .
H11 H 0.9355 1.0354 0.2088 0.120 Uiso 1 1 calc R . . . .
C12 C 0.6384(6) 1.00969(17) 0.19613(16) 0.1161(11) Uani 1 1 d . . . . .
H12 H 0.6033 1.0585 0.1708 0.139 Uiso 1 1 calc R . . . .
C13 C 0.4898(4) 0.9514(2) 0.21031(17) 0.1296(12) Uani 1 1 d . . . . .
H13 H 0.3538 0.9607 0.1947 0.156 Uiso 1 1 calc R . . . .
C14 C 0.5430(4) 0.87838(15) 0.24809(13) 0.0963(9) Uani 1 1 d . . . . .
H14 H 0.4416 0.8391 0.2581 0.116 Uiso 1 1 calc R . . . .
C15 C 0.7372(3) 0.71482(11) 0.22641(9) 0.0523(5) Uani 1 1 d . . . . .
C16 C 0.8358(4) 0.75853(13) 0.16581(10) 0.0722(6) Uani 1 1 d . . . . .
H16 H 0.9421 0.7935 0.1661 0.087 Uiso 1 1 calc R . . . .
C17 C 0.7819(4) 0.75209(14) 0.10492(11) 0.0818(7) Uani 1 1 d . . . . .
H17 H 0.8521 0.7826 0.0650 0.098 Uiso 1 1 calc R . . . .
C18 C 0.6252(4) 0.70102(14) 0.10185(11) 0.0734(6) Uani 1 1 d . . . . .
C19 C 0.5300(3) 0.65539(14) 0.16165(11) 0.0746(6) Uani 1 1 d . . . . .
H19 H 0.4264 0.6196 0.1610 0.090 Uiso 1 1 calc R . . . .
C20 C 0.5854(3) 0.66169(12) 0.22257(10) 0.0645(6) Uani 1 1 d . . . . .
H20 H 0.5195 0.6295 0.2623 0.077 Uiso 1 1 calc R . . . .
C21 C 0.8436(3) 0.64384(10) 0.33828(9) 0.0459(4) Uani 1 1 d . . . . .
C22 C 0.7241(3) 0.61729(12) 0.40107(10) 0.0581(5) Uani 1 1 d . . . . .
H22 H 0.6096 0.6480 0.4163 0.070 Uiso 1 1 calc R . . . .
C23 C 0.7706(4) 0.54662(13) 0.44157(10) 0.0693(6) Uani 1 1 d . . . . .
H23 H 0.6867 0.5299 0.4836 0.083 Uiso 1 1 calc R . . . .
C24 C 0.9380(4) 0.50069(12) 0.42094(11) 0.0676(6) Uani 1 1 d . . . . .
H24 H 0.9695 0.4530 0.4488 0.081 Uiso 1 1 calc R . . . .
C25 C 1.0593(3) 0.52522(13) 0.35911(11) 0.0655(6) Uani 1 1 d . . . . .
H25 H 1.1752 0.4943 0.3449 0.079 Uiso 1 1 calc R . . . .
C26 C 1.0109(3) 0.59563(12) 0.31757(10) 0.0570(5) Uani 1 1 d . . . . .
H26 H 1.0919 0.6110 0.2750 0.068 Uiso 1 1 calc R . . . .
N3 N 0.1279(3) 0.60150(10) 0.02800(10) 0.0868(6) Uani 1 1 d . . . . .
H3A H 0.1215 0.5916 -0.0107 0.104 Uiso 1 1 d GR . . . .
H3B H 0.0103 0.6268 0.0394 0.104 Uiso 1 1 d GR . . . .
N4 N 0.3666(4) -0.01229(11) 0.43726(10) 0.0802(6) Uani 1 1 d . . . . .
H4A H 0.2727 -0.0479 0.4416 0.096 Uiso 1 1 d GR . . . .
C27 C 0.2400(3) 0.32729(10) 0.23381(9) 0.0458(4) Uani 1 1 d . . . . .
C28 C 0.1977(3) 0.25446(10) 0.23172(9) 0.0444(4) Uani 1 1 d . . . . .
C29 C 0.2033(3) 0.39672(10) 0.17853(9) 0.0464(4) Uani 1 1 d . . . . .
C30 C 0.0978(3) 0.46266(11) 0.19388(9) 0.0533(5) Uani 1 1 d . . . . .
H30 H 0.0475 0.4623 0.2388 0.064 Uiso 1 1 calc R . . . .
C31 C 0.0650(3) 0.52848(11) 0.14484(11) 0.0613(5) Uani 1 1 d . . . . .
H31 H -0.0098 0.5710 0.1571 0.074 Uiso 1 1 calc R . . . .
C32 C 0.1416(3) 0.53215(12) 0.07772(10) 0.0587(5) Uani 1 1 d . . . . .
C33 C 0.2464(3) 0.46723(13) 0.06119(10) 0.0616(5) Uani 1 1 d . . . . .
H33 H 0.2977 0.4681 0.0162 0.074 Uiso 1 1 calc R . . . .
C34 C 0.2761(3) 0.40087(11) 0.11053(10) 0.0587(5) Uani 1 1 d . . . . .
H34 H 0.3467 0.3579 0.0979 0.070 Uiso 1 1 calc R . . . .
C35 C 0.3283(3) 0.34466(10) 0.29253(9) 0.0449(4) Uani 1 1 d . . . . .
C36 C 0.5134(3) 0.38954(11) 0.28197(10) 0.0582(5) Uani 1 1 d . . . . .
H36 H 0.5794 0.4102 0.2381 0.070 Uiso 1 1 calc R . . . .
C37 C 0.6005(3) 0.40372(13) 0.33616(11) 0.0700(6) Uani 1 1 d . . . . .
H37 H 0.7255 0.4332 0.3285 0.084 Uiso 1 1 calc R . . . .
C38 C 0.5035(3) 0.37455(12) 0.40114(11) 0.0679(6) Uani 1 1 d . . . . .
H38 H 0.5645 0.3832 0.4374 0.082 Uiso 1 1 calc R . . . .
C39 C 0.3163(4) 0.33263(11) 0.41224(10) 0.0627(5) Uani 1 1 d . . . . .
H39 H 0.2477 0.3139 0.4561 0.075 Uiso 1 1 calc R . . . .
C40 C 0.2300(3) 0.31819(10) 0.35857(9) 0.0551(5) Uani 1 1 d . . . . .
H40 H 0.1023 0.2899 0.3668 0.066 Uiso 1 1 calc R . . . .
C41 C 0.2507(3) 0.18406(10) 0.28351(8) 0.0421(4) Uani 1 1 d . . . . .
C42 C 0.4473(3) 0.17117(10) 0.31051(9) 0.0497(5) Uani 1 1 d . . . . .
H42 H 0.5567 0.2076 0.2949 0.060 Uiso 1 1 calc R . . . .
C43 C 0.4856(3) 0.10649(11) 0.35942(9) 0.0520(5) Uani 1 1 d . . . . .
H43 H 0.6197 0.1001 0.3762 0.062 Uiso 1 1 calc R . . . .
C44 C 0.3290(3) 0.05045(10) 0.38435(9) 0.0510(5) Uani 1 1 d . . . . .
C45 C 0.1350(3) 0.06065(11) 0.35667(10) 0.0544(5) Uani 1 1 d . . . . .
H45 H 0.0281 0.0232 0.3716 0.065 Uiso 1 1 calc R . . . .
C46 C 0.0977(3) 0.12585(10) 0.30708(9) 0.0498(5) Uani 1 1 d . . . . .
H46 H -0.0339 0.1310 0.2889 0.060 Uiso 1 1 calc R . . . .
C47 C 0.0888(3) 0.23808(10) 0.17628(9) 0.0430(4) Uani 1 1 d . . . . .
C48 C -0.1148(3) 0.27041(11) 0.16220(10) 0.0574(5) Uani 1 1 d . . . . .
H48 H -0.1836 0.3056 0.1860 0.069 Uiso 1 1 calc R . . . .
C49 C -0.2159(3) 0.25081(14) 0.11322(12) 0.0743(6) Uani 1 1 d . . . . .
H49 H -0.3525 0.2731 0.1044 0.089 Uiso 1 1 calc R . . . .
C50 C -0.1207(4) 0.19986(15) 0.07757(12) 0.0781(7) Uani 1 1 d . . . . .
H50 H -0.1907 0.1874 0.0445 0.094 Uiso 1 1 calc R . . . .
C51 C 0.0802(4) 0.16683(12) 0.09092(10) 0.0699(6) Uani 1 1 d . . . . .
H51 H 0.1474 0.1319 0.0666 0.084 Uiso 1 1 calc R . . . .
C52 C 0.1835(3) 0.18514(11) 0.14034(10) 0.0545(5) Uani 1 1 d . . . . .
H52 H 0.3184 0.1616 0.1496 0.065 Uiso 1 1 calc R . . . .
H4B H 0.497(4) -0.0168(16) 0.4523(14) 0.127(11) 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
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C6 1.389(2) . ?
N2 H2A 0.8706 . ?
N2 H2B 0.8689 . ?
N2 C18 1.406(3) . ?
C1 C2 1.350(2) . ?
C1 C3 1.493(3) . ?
C1 C9 1.499(3) . ?
C2 C15 1.489(3) . ?
C2 C21 1.488(2) . ?
C3 C4 1.383(2) . ?
C3 C8 1.388(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.372(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(3) . ?
C6 C7 1.378(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.374(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.376(3) . ?
C9 C14 1.372(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.364(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.342(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.373(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.392(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.377(3) . ?
C15 C20 1.390(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.373(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.381(3) . ?
C18 C19 1.372(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.376(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.379(2) . ?
C21 C26 1.386(2) . ?
C22 H22 0.9300 . ?
C22 C23 1.371(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.359(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.364(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.380(3) . ?
C26 H26 0.9300 . ?
N3 H3A 0.8619 . ?
N3 H3B 0.8618 . ?
N3 C32 1.408(2) . ?
N4 H4A 0.8631 . ?
N4 C44 1.394(2) . ?
N4 H4B 0.89(3) . ?
C27 C28 1.349(2) . ?
C27 C29 1.495(2) . ?
C27 C35 1.496(2) . ?
C28 C41 1.490(2) . ?
C28 C47 1.496(2) . ?
C29 C30 1.388(2) . ?
C29 C34 1.391(2) . ?
C30 H30 0.9300 . ?
C30 C31 1.376(2) . ?
C31 H31 0.9300 . ?
C31 C32 1.379(3) . ?
C32 C33 1.379(3) . ?
C33 H33 0.9300 . ?
C33 C34 1.382(3) . ?
C34 H34 0.9300 . ?
C35 C36 1.390(2) . ?
C35 C40 1.385(2) . ?
C36 H36 0.9300 . ?
C36 C37 1.384(3) . ?
C37 H37 0.9300 . ?
C37 C38 1.372(3) . ?
C38 H38 0.9300 . ?
C38 C39 1.370(3) . ?
C39 H39 0.9300 . ?
C39 C40 1.374(3) . ?
C40 H40 0.9300 . ?
C41 C42 1.387(2) . ?
C41 C46 1.391(2) . ?
C42 H42 0.9300 . ?
C42 C43 1.368(2) . ?
C43 H43 0.9300 . ?
C43 C44 1.382(2) . ?
C44 C45 1.379(2) . ?
C45 H45 0.9300 . ?
C45 C46 1.380(2) . ?
C46 H46 0.9300 . ?
C47 C48 1.386(2) . ?
C47 C52 1.385(2) . ?
C48 H48 0.9300 . ?
C48 C49 1.378(3) . ?
C49 H49 0.9300 . ?
C49 C50 1.354(3) . ?
C50 H50 0.9300 . ?
C50 C51 1.372(3) . ?
C51 H51 0.9300 . ?
C51 C52 1.383(3) . ?
C52 H52 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
H1A N1 H1B 120.0 . . ?
C6 N1 H1A 120.0 . . ?
C6 N1 H1B 120.0 . . ?
H2A N2 H2B 107.8 . . ?
C18 N2 H2A 110.8 . . ?
C18 N2 H2B 108.6 . . ?
C2 C1 C3 123.22(17) . . ?
C2 C1 C9 122.81(17) . . ?
C3 C1 C9 113.91(16) . . ?
C1 C2 C15 124.56(18) . . ?
C1 C2 C21 121.12(17) . . ?
C21 C2 C15 114.29(16) . . ?
C4 C3 C1 120.74(17) . . ?
C4 C3 C8 116.49(18) . . ?
C8 C3 C1 122.57(16) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 C3 122.15(18) . . ?
C5 C4 H4 118.9 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.88(18) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 N1 121.13(19) . . ?
C7 C6 N1 121.36(19) . . ?
C7 C6 C5 117.44(18) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 C6 121.47(18) . . ?
C8 C7 H7 119.3 . . ?
C3 C8 H8 119.2 . . ?
C7 C8 C3 121.57(18) . . ?
C7 C8 H8 119.2 . . ?
C10 C9 C1 119.70(18) . . ?
C14 C9 C1 122.81(19) . . ?
C14 C9 C10 117.4(2) . . ?
C9 C10 H10 118.9 . . ?
C11 C10 C9 122.2(2) . . ?
C11 C10 H10 118.9 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.2(3) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 119.9(3) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.9(3) . . ?
C14 C13 H13 120.1 . . ?
C9 C14 C13 120.4(2) . . ?
C9 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C2 123.00(17) . . ?
C16 C15 C20 116.35(18) . . ?
C20 C15 C2 120.58(17) . . ?
C15 C16 H16 119.0 . . ?
C17 C16 C15 122.0(2) . . ?
C17 C16 H16 119.0 . . ?
C16 C17 H17 119.4 . . ?
C16 C17 C18 121.1(2) . . ?
C18 C17 H17 119.4 . . ?
C17 C18 N2 120.8(2) . . ?
C19 C18 N2 121.4(2) . . ?
C19 C18 C17 117.7(2) . . ?
C18 C19 H19 119.5 . . ?
C18 C19 C20 121.0(2) . . ?
C20 C19 H19 119.5 . . ?
C15 C20 H20 119.1 . . ?
C19 C20 C15 121.81(19) . . ?
C19 C20 H20 119.1 . . ?
C22 C21 C2 122.47(16) . . ?
C22 C21 C26 117.13(17) . . ?
C26 C21 C2 120.39(16) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 C21 121.43(18) . . ?
C23 C22 H22 119.3 . . ?
C22 C23 H23 119.7 . . ?
C24 C23 C22 120.63(19) . . ?
C24 C23 H23 119.7 . . ?
C23 C24 H24 120.3 . . ?
C23 C24 C25 119.4(2) . . ?
C25 C24 H24 120.3 . . ?
C24 C25 H25 119.9 . . ?
C24 C25 C26 120.27(19) . . ?
C26 C25 H25 119.9 . . ?
C21 C26 H26 119.5 . . ?
C25 C26 C21 121.10(18) . . ?
C25 C26 H26 119.5 . . ?
H3A N3 H3B 109.3 . . ?
C32 N3 H3A 110.2 . . ?
C32 N3 H3B 108.5 . . ?
H4A N4 H4B 128.2 . . ?
C44 N4 H4A 110.6 . . ?
C44 N4 H4B 118.3(18) . . ?
C28 C27 C29 123.40(17) . . ?
C28 C27 C35 121.98(16) . . ?
C29 C27 C35 114.62(15) . . ?
C27 C28 C41 124.11(16) . . ?
C27 C28 C47 121.77(16) . . ?
C41 C28 C47 114.12(15) . . ?
C30 C29 C27 120.22(16) . . ?
C30 C29 C34 116.26(17) . . ?
C34 C29 C27 123.48(16) . . ?
C29 C30 H30 118.9 . . ?
C31 C30 C29 122.24(17) . . ?
C31 C30 H30 118.9 . . ?
C30 C31 H31 119.6 . . ?
C30 C31 C32 120.80(19) . . ?
C32 C31 H31 119.6 . . ?
C31 C32 N3 121.3(2) . . ?
C31 C32 C33 118.01(18) . . ?
C33 C32 N3 120.6(2) . . ?
C32 C33 H33 119.5 . . ?
C32 C33 C34 120.95(18) . . ?
C34 C33 H33 119.5 . . ?
C29 C34 H34 119.1 . . ?
C33 C34 C29 121.71(18) . . ?
C33 C34 H34 119.1 . . ?
C36 C35 C27 120.23(16) . . ?
C40 C35 C27 122.23(16) . . ?
C40 C35 C36 117.54(17) . . ?
C35 C36 H36 119.7 . . ?
C37 C36 C35 120.58(18) . . ?
C37 C36 H36 119.7 . . ?
C36 C37 H37 119.8 . . ?
C38 C37 C36 120.46(19) . . ?
C38 C37 H37 119.8 . . ?
C37 C38 H38 120.2 . . ?
C39 C38 C37 119.6(2) . . ?
C39 C38 H38 120.2 . . ?
C38 C39 H39 120.0 . . ?
C38 C39 C40 120.02(19) . . ?
C40 C39 H39 120.0 . . ?
C35 C40 H40 119.2 . . ?
C39 C40 C35 121.68(18) . . ?
C39 C40 H40 119.2 . . ?
C42 C41 C28 124.31(15) . . ?
C42 C41 C46 116.07(16) . . ?
C46 C41 C28 119.62(15) . . ?
C41 C42 H42 119.0 . . ?
C43 C42 C41 122.06(17) . . ?
C43 C42 H42 119.0 . . ?
C42 C43 H43 119.3 . . ?
C42 C43 C44 121.35(17) . . ?
C44 C43 H43 119.3 . . ?
C43 C44 N4 120.09(19) . . ?
C45 C44 N4 122.19(18) . . ?
C45 C44 C43 117.68(17) . . ?
C44 C45 H45 119.6 . . ?
C44 C45 C46 120.71(16) . . ?
C46 C45 H45 119.6 . . ?
C41 C46 H46 119.0 . . ?
C45 C46 C41 122.05(16) . . ?
C45 C46 H46 119.0 . . ?
C48 C47 C28 121.94(16) . . ?
C52 C47 C28 120.13(16) . . ?
C52 C47 C48 117.78(18) . . ?
C47 C48 H48 119.8 . . ?
C49 C48 C47 120.4(2) . . ?
C49 C48 H48 119.8 . . ?
C48 C49 H49 119.3 . . ?
C50 C49 C48 121.5(2) . . ?
C50 C49 H49 119.3 . . ?
C49 C50 H50 120.5 . . ?
C49 C50 C51 119.1(2) . . ?
C51 C50 H50 120.5 . . ?
C50 C51 H51 119.8 . . ?
C50 C51 C52 120.3(2) . . ?
C52 C51 H51 119.8 . . ?
C47 C52 H52 119.6 . . ?
C51 C52 C47 120.87(18) . . ?
C51 C52 H52 119.6 . . ?

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
N1 C6 C7 C8 -177.45(17) . . . . ?
N2 C18 C19 C20 176.3(2) . . . . ?
C1 C2 C15 C16 48.4(3) . . . . ?
C1 C2 C15 C20 -134.8(2) . . . . ?
C1 C2 C21 C22 61.8(2) . . . . ?
C1 C2 C21 C26 -119.68(19) . . . . ?
C1 C3 C4 C5 -176.14(17) . . . . ?
C1 C3 C8 C7 175.25(17) . . . . ?
C1 C9 C10 C11 179.6(2) . . . . ?
C1 C9 C14 C13 179.5(2) . . . . ?
C2 C1 C3 C4 -135.50(19) . . . . ?
C2 C1 C3 C8 49.9(2) . . . . ?
C2 C1 C9 C10 -130.8(2) . . . . ?
C2 C1 C9 C14 51.9(3) . . . . ?
C2 C15 C16 C17 179.1(2) . . . . ?
C2 C15 C20 C19 -179.60(19) . . . . ?
C2 C21 C22 C23 179.31(18) . . . . ?
C2 C21 C26 C25 179.45(18) . . . . ?
C3 C1 C2 C15 -169.59(16) . . . . ?
C3 C1 C2 C21 8.4(3) . . . . ?
C3 C1 C9 C10 46.4(2) . . . . ?
C3 C1 C9 C14 -130.8(2) . . . . ?
C3 C4 C5 C6 1.2(3) . . . . ?
C4 C3 C8 C7 0.4(3) . . . . ?
C4 C5 C6 N1 176.68(17) . . . . ?
C4 C5 C6 C7 -0.3(3) . . . . ?
C5 C6 C7 C8 -0.4(3) . . . . ?
C6 C7 C8 C3 0.4(3) . . . . ?
C8 C3 C4 C5 -1.2(3) . . . . ?
C9 C1 C2 C15 7.4(3) . . . . ?
C9 C1 C2 C21 -174.63(15) . . . . ?
C9 C1 C3 C4 47.2(2) . . . . ?
C9 C1 C3 C8 -127.39(18) . . . . ?
C9 C10 C11 C12 2.3(4) . . . . ?
C10 C9 C14 C13 2.2(4) . . . . ?
C10 C11 C12 C13 -0.6(5) . . . . ?
C11 C12 C13 C14 -0.1(5) . . . . ?
C12 C13 C14 C9 -0.7(5) . . . . ?
C14 C9 C10 C11 -3.1(3) . . . . ?
C15 C2 C21 C22 -120.06(19) . . . . ?
C15 C2 C21 C26 58.5(2) . . . . ?
C15 C16 C17 C18 0.0(4) . . . . ?
C16 C15 C20 C19 -2.6(3) . . . . ?
C16 C17 C18 N2 -176.8(2) . . . . ?
C16 C17 C18 C19 -1.8(4) . . . . ?
C17 C18 C19 C20 1.5(3) . . . . ?
C18 C19 C20 C15 0.8(3) . . . . ?
C20 C15 C16 C17 2.2(3) . . . . ?
C21 C2 C15 C16 -129.6(2) . . . . ?
C21 C2 C15 C20 47.2(2) . . . . ?
C21 C22 C23 C24 0.5(3) . . . . ?
C22 C21 C26 C25 -1.9(3) . . . . ?
C22 C23 C24 C25 -0.5(3) . . . . ?
C23 C24 C25 C26 -0.7(3) . . . . ?
C24 C25 C26 C21 2.0(3) . . . . ?
C26 C21 C22 C23 0.7(3) . . . . ?
N3 C32 C33 C34 174.74(18) . . . . ?
N4 C44 C45 C46 176.06(19) . . . . ?
C27 C28 C41 C42 -44.0(3) . . . . ?
C27 C28 C41 C46 136.64(18) . . . . ?
C27 C28 C47 C48 -56.8(2) . . . . ?
C27 C28 C47 C52 127.81(18) . . . . ?
C27 C29 C30 C31 178.45(17) . . . . ?
C27 C29 C34 C33 -177.43(17) . . . . ?
C27 C35 C36 C37 -177.83(17) . . . . ?
C27 C35 C40 C39 178.06(17) . . . . ?
C28 C27 C29 C30 133.77(18) . . . . ?
C28 C27 C29 C34 -48.4(3) . . . . ?
C28 C27 C35 C36 128.78(18) . . . . ?
C28 C27 C35 C40 -52.0(2) . . . . ?
C28 C41 C42 C43 178.10(17) . . . . ?
C28 C41 C46 C45 -177.75(16) . . . . ?
C28 C47 C48 C49 -176.46(17) . . . . ?
C28 C47 C52 C51 177.18(16) . . . . ?
C29 C27 C28 C41 174.68(15) . . . . ?
C29 C27 C28 C47 -6.2(2) . . . . ?
C29 C27 C35 C36 -51.3(2) . . . . ?
C29 C27 C35 C40 127.94(17) . . . . ?
C29 C30 C31 C32 -1.6(3) . . . . ?
C30 C29 C34 C33 0.5(3) . . . . ?
C30 C31 C32 N3 -173.78(18) . . . . ?
C30 C31 C32 C33 1.8(3) . . . . ?
C31 C32 C33 C34 -0.8(3) . . . . ?
C32 C33 C34 C29 -0.3(3) . . . . ?
C34 C29 C30 C31 0.5(3) . . . . ?
C35 C27 C28 C41 -5.4(2) . . . . ?
C35 C27 C28 C47 173.80(14) . . . . ?
C35 C27 C29 C30 -46.2(2) . . . . ?
C35 C27 C29 C34 131.64(18) . . . . ?
C35 C36 C37 C38 -0.9(3) . . . . ?
C36 C35 C40 C39 -2.7(3) . . . . ?
C36 C37 C38 C39 -1.5(3) . . . . ?
C37 C38 C39 C40 1.8(3) . . . . ?
C38 C39 C40 C35 0.4(3) . . . . ?
C40 C35 C36 C37 2.9(3) . . . . ?
C41 C28 C47 C48 122.46(17) . . . . ?
C41 C28 C47 C52 -53.0(2) . . . . ?
C41 C42 C43 C44 0.1(3) . . . . ?
C42 C41 C46 C45 2.8(3) . . . . ?
C42 C43 C44 N4 -175.78(18) . . . . ?
C42 C43 C44 C45 2.1(3) . . . . ?
C43 C44 C45 C46 -1.7(3) . . . . ?
C44 C45 C46 C41 -0.8(3) . . . . ?
C46 C41 C42 C43 -2.5(3) . . . . ?
C47 C28 C41 C42 136.78(17) . . . . ?
C47 C28 C41 C46 -42.6(2) . . . . ?
C47 C48 C49 C50 0.0(3) . . . . ?
C48 C47 C52 C51 1.6(3) . . . . ?
C48 C49 C50 C51 0.4(3) . . . . ?
C49 C50 C51 C52 0.3(3) . . . . ?
C50 C51 C52 C47 -1.3(3) . . . . ?
C52 C47 C48 C49 -0.9(3) . . . . ?

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

data_O-2NH2-TPE
_database_code_depnum_ccdc_archive 'CCDC 2120061'
loop_
_audit_author_name
_audit_author_address
lx
;Sichuan University
China
;
_audit_update_record             
;
2021-11-03 deposited with the CCDC.	2022-01-04 downloaded from the CCDC.
;
_audit_creation_date             2021-01-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C26 H22 N2 O'
_chemical_formula_sum            'C26 H22 N2 O'
_chemical_formula_weight         378.45
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3br1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_H-M_alt        'P 43 21 2'
_space_group_name_Hall           'P 4nw 2abw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y+1/2, x+1/2, z+3/4'
'-x, -y, z+1/2'
'y+1/2, -x+1/2, z+1/4'
'x+1/2, -y+1/2, -z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   10.1318(5)
_cell_length_b                   10.1318(5)
_cell_length_c                   39.042(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4007.7(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1204
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.6250
_cell_measurement_theta_min      3.2340
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98394
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0747
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            8119
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.843
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -65.00  -36.20   0.3000  175.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.3211 -178.0000  -60.0000 96

#__ type_ start__ end____ width___ exp.time_
  2 omega  -43.00   24.50   0.3000  175.0000
omega____ theta____ kappa____ phi______ frames
    -       17.3523  -77.0000  -90.0000 225
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0685507000
_diffrn_orient_matrix_UB_12      0.0066858000
_diffrn_orient_matrix_UB_13      0.0033092000
_diffrn_orient_matrix_UB_21      0.0092416000
_diffrn_orient_matrix_UB_22      0.0680114000
_diffrn_orient_matrix_UB_23      0.0035662000
_diffrn_orient_matrix_UB_31      -0.0110621000
_diffrn_orient_matrix_UB_32      0.0151386000
_diffrn_orient_matrix_UB_33      -0.0174958000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.665
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                2513
_reflns_number_total             4025
_reflns_odcompleteness_completeness 96.86
_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, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 660 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.7(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         4025
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1054
_refine_ls_R_factor_gt           0.0564
_refine_ls_restrained_S_all      0.996
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0370P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.1058
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C16(H16), C17(H17), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24),
  C25(H25), C26(H26)
;
_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
O1 O 0.4020(3) 0.1601(2) 0.49194(6) 0.0527(7) Uani 1 1 d . . . . .
N1 N 0.2999(4) -0.2819(4) 0.36791(11) 0.0687(11) Uani 1 1 d . . . . .
H1A H 0.346(4) -0.283(4) 0.3449(11) 0.089(16) Uiso 1 1 d . . . . .
H1B H 0.200(7) -0.282(7) 0.3664(16) 0.21(3) Uiso 1 1 d . . . . .
N2 N 1.1264(3) 0.1496(4) 0.45556(9) 0.0616(10) Uani 1 1 d . . . . .
H2A H 1.188(4) 0.072(4) 0.4581(10) 0.079(13) Uiso 1 1 d . . . . .
H2B H 1.134(6) 0.242(6) 0.4684(14) 0.17(3) Uiso 1 1 d . . . . .
C1 C 0.4843(3) 0.1463(3) 0.46925(9) 0.0375(8) Uani 1 1 d . . . . .
C2 C 0.5754(3) 0.0231(3) 0.46975(8) 0.0361(8) Uani 1 1 d . . . . .
C3 C 0.4866(3) 0.2465(3) 0.44112(9) 0.0382(8) Uani 1 1 d . . . . .
C4 C 0.4126(4) 0.3613(3) 0.44573(10) 0.0506(10) Uani 1 1 d . . . . .
H4 H 0.3638 0.3724 0.4657 0.061 Uiso 1 1 calc R . . . .
C5 C 0.4112(4) 0.4587(4) 0.42102(11) 0.0661(12) Uani 1 1 d . . . . .
H5 H 0.3621 0.5350 0.4245 0.079 Uiso 1 1 calc R . . . .
C6 C 0.4827(4) 0.4429(4) 0.39111(11) 0.0655(12) Uani 1 1 d . . . . .
H6 H 0.4818 0.5085 0.3744 0.079 Uiso 1 1 calc R . . . .
C7 C 0.5546(4) 0.3306(4) 0.38628(10) 0.0586(11) Uani 1 1 d . . . . .
H7 H 0.6024 0.3197 0.3661 0.070 Uiso 1 1 calc R . . . .
C8 C 0.5572(4) 0.2337(4) 0.41074(9) 0.0509(10) Uani 1 1 d . . . . .
H8 H 0.6071 0.1580 0.4070 0.061 Uiso 1 1 calc R . . . .
C9 C 0.5101(3) -0.0635(3) 0.44177(8) 0.0375(8) Uani 1 1 d . . . . .
C10 C 0.5691(4) -0.1016(3) 0.41108(9) 0.0465(9) Uani 1 1 d . . . . .
H10 H 0.6566 -0.0790 0.4070 0.056 Uiso 1 1 calc R . . . .
C11 C 0.5002(4) -0.1725(3) 0.38657(9) 0.0504(10) Uani 1 1 d . . . . .
H11 H 0.5427 -0.1976 0.3665 0.061 Uiso 1 1 calc R . . . .
C12 C 0.3696(4) -0.2067(3) 0.39141(10) 0.0481(10) Uani 1 1 d . . . . .
C13 C 0.3102(4) -0.1704(4) 0.42211(10) 0.0523(10) Uani 1 1 d . . . . .
H13 H 0.2228 -0.1933 0.4262 0.063 Uiso 1 1 calc R . . . .
C14 C 0.3793(3) -0.1014(3) 0.44622(9) 0.0456(9) Uani 1 1 d . . . . .
H14 H 0.3370 -0.0788 0.4665 0.055 Uiso 1 1 calc R . . . .
C15 C 0.7211(3) 0.0579(3) 0.46421(8) 0.0365(8) Uani 1 1 d . . . . .
C16 C 0.7695(3) 0.1847(3) 0.46857(9) 0.0427(9) Uani 1 1 d . . . . .
H16 H 0.7106 0.2524 0.4736 0.051 Uiso 1 1 calc R . . . .
C17 C 0.9025(3) 0.2144(4) 0.46574(9) 0.0451(9) Uani 1 1 d . . . . .
H17 H 0.9309 0.3012 0.4682 0.054 Uiso 1 1 calc R . . . .
C18 C 0.9927(3) 0.1163(4) 0.45933(8) 0.0419(9) Uani 1 1 d . . . . .
C19 C 0.9479(3) -0.0127(4) 0.45601(8) 0.0463(9) Uani 1 1 d . . . . .
H19 H 1.0078 -0.0806 0.4521 0.056 Uiso 1 1 calc R . . . .
C20 C 0.8148(3) -0.0405(3) 0.45851(8) 0.0425(9) Uani 1 1 d . . . . .
H20 H 0.7868 -0.1275 0.4563 0.051 Uiso 1 1 calc R . . . .
C21 C 0.5699(3) -0.0447(3) 0.50490(9) 0.0404(9) Uani 1 1 d . . . . .
C22 C 0.5855(4) 0.0292(4) 0.53478(10) 0.0539(10) Uani 1 1 d . . . . .
H22 H 0.5962 0.1202 0.5332 0.065 Uiso 1 1 calc R . . . .
C23 C 0.5855(4) -0.0303(5) 0.56670(10) 0.0687(13) Uani 1 1 d . . . . .
H23 H 0.5954 0.0210 0.5863 0.082 Uiso 1 1 calc R . . . .
C24 C 0.5709(4) -0.1652(5) 0.56963(12) 0.0699(13) Uani 1 1 d . . . . .
H24 H 0.5692 -0.2049 0.5911 0.084 Uiso 1 1 calc R . . . .
C25 C 0.5588(4) -0.2402(4) 0.54050(11) 0.0615(12) Uani 1 1 d . . . . .
H25 H 0.5511 -0.3315 0.5422 0.074 Uiso 1 1 calc R . . . .
C26 C 0.5579(3) -0.1806(4) 0.50842(10) 0.0500(10) Uani 1 1 d . . . . .
H26 H 0.5492 -0.2327 0.4889 0.060 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.225(4) . ?
N1 H1A 1.01(4) . ?
N1 H1B 1.01(7) . ?
N1 C12 1.386(5) . ?
N2 H2A 1.01(4) . ?
N2 H2B 1.06(6) . ?
N2 C18 1.404(5) . ?
C1 C2 1.553(4) . ?
C1 C3 1.495(5) . ?
C2 C9 1.549(4) . ?
C2 C15 1.533(4) . ?
C2 C21 1.536(4) . ?
C3 C4 1.396(5) . ?
C3 C8 1.391(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.379(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.383(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.364(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.370(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.393(4) . ?
C9 C14 1.391(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.385(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.381(5) . ?
C12 C13 1.391(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.366(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.386(4) . ?
C15 C20 1.395(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.385(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.373(5) . ?
C18 C19 1.390(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.381(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.395(5) . ?
C21 C26 1.389(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.384(5) . ?
C23 H23 0.9300 . ?
C23 C24 1.380(6) . ?
C24 H24 0.9300 . ?
C24 C25 1.373(5) . ?
C25 H25 0.9300 . ?
C25 C26 1.391(5) . ?
C26 H26 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
H1A N1 H1B 114(4) . . ?
C12 N1 H1A 111(2) . . ?
C12 N1 H1B 123(4) . . ?
H2A N2 H2B 127(4) . . ?
C18 N2 H2A 114(2) . . ?
C18 N2 H2B 103(3) . . ?
O1 C1 C2 119.2(3) . . ?
O1 C1 C3 117.7(3) . . ?
C3 C1 C2 123.1(3) . . ?
C9 C2 C1 101.1(3) . . ?
C15 C2 C1 112.7(3) . . ?
C15 C2 C9 116.2(3) . . ?
C15 C2 C21 105.3(3) . . ?
C21 C2 C1 110.4(3) . . ?
C21 C2 C9 111.2(3) . . ?
C4 C3 C1 117.6(3) . . ?
C8 C3 C1 124.8(3) . . ?
C8 C3 C4 117.6(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.8(3) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.2(4) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 H6 120.3 . . ?
C7 C6 C5 119.5(4) . . ?
C7 C6 H6 120.3 . . ?
C6 C7 H7 119.6 . . ?
C6 C7 C8 120.8(4) . . ?
C8 C7 H7 119.6 . . ?
C3 C8 H8 119.4 . . ?
C7 C8 C3 121.2(3) . . ?
C7 C8 H8 119.4 . . ?
C10 C9 C2 125.5(3) . . ?
C14 C9 C2 118.4(3) . . ?
C14 C9 C10 116.1(3) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 C9 121.5(4) . . ?
C11 C10 H10 119.3 . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.2(4) . . ?
C12 C11 H11 119.4 . . ?
N1 C12 C13 119.7(4) . . ?
C11 C12 N1 122.4(4) . . ?
C11 C12 C13 117.8(4) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.5(4) . . ?
C14 C13 H13 119.7 . . ?
C9 C14 H14 118.5 . . ?
C13 C14 C9 122.9(3) . . ?
C13 C14 H14 118.5 . . ?
C16 C15 C2 122.5(3) . . ?
C16 C15 C20 116.2(3) . . ?
C20 C15 C2 120.9(3) . . ?
C15 C16 H16 118.8 . . ?
C17 C16 C15 122.4(3) . . ?
C17 C16 H16 118.8 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.3(3) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 N2 119.2(4) . . ?
C17 C18 C19 118.7(3) . . ?
C19 C18 N2 122.1(3) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.3(3) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 H20 119.0 . . ?
C19 C20 C15 122.0(3) . . ?
C19 C20 H20 119.0 . . ?
C22 C21 C2 120.2(3) . . ?
C26 C21 C2 122.3(3) . . ?
C26 C21 C22 117.3(3) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 C21 121.3(4) . . ?
C23 C22 H22 119.4 . . ?
C22 C23 H23 119.8 . . ?
C24 C23 C22 120.4(4) . . ?
C24 C23 H23 119.8 . . ?
C23 C24 H24 120.3 . . ?
C25 C24 C23 119.3(4) . . ?
C25 C24 H24 120.3 . . ?
C24 C25 H25 119.8 . . ?
C24 C25 C26 120.4(4) . . ?
C26 C25 H25 119.8 . . ?
C21 C26 C25 121.3(4) . . ?
C21 C26 H26 119.4 . . ?
C25 C26 H26 119.4 . . ?

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
O1 C1 C2 C9 102.8(3) . . . . ?
O1 C1 C2 C15 -132.4(3) . . . . ?
O1 C1 C2 C21 -15.0(4) . . . . ?
O1 C1 C3 C4 11.7(5) . . . . ?
O1 C1 C3 C8 -168.5(3) . . . . ?
N1 C12 C13 C14 177.0(4) . . . . ?
N2 C18 C19 C20 -177.3(3) . . . . ?
C1 C2 C9 C10 116.4(3) . . . . ?
C1 C2 C9 C14 -59.8(4) . . . . ?
C1 C2 C15 C16 18.0(5) . . . . ?
C1 C2 C15 C20 -169.9(3) . . . . ?
C1 C2 C21 C22 -49.2(4) . . . . ?
C1 C2 C21 C26 135.0(3) . . . . ?
C1 C3 C4 C5 179.3(3) . . . . ?
C1 C3 C8 C7 -179.6(3) . . . . ?
C2 C1 C3 C4 -171.8(3) . . . . ?
C2 C1 C3 C8 8.0(5) . . . . ?
C2 C9 C10 C11 -176.0(3) . . . . ?
C2 C9 C14 C13 175.7(3) . . . . ?
C2 C15 C16 C17 175.7(3) . . . . ?
C2 C15 C20 C19 -175.1(3) . . . . ?
C2 C21 C22 C23 -177.8(3) . . . . ?
C2 C21 C26 C25 177.3(3) . . . . ?
C3 C1 C2 C9 -73.6(3) . . . . ?
C3 C1 C2 C15 51.2(4) . . . . ?
C3 C1 C2 C21 168.6(3) . . . . ?
C3 C4 C5 C6 0.5(6) . . . . ?
C4 C3 C8 C7 0.2(5) . . . . ?
C4 C5 C6 C7 0.0(6) . . . . ?
C5 C6 C7 C8 -0.3(6) . . . . ?
C6 C7 C8 C3 0.2(6) . . . . ?
C8 C3 C4 C5 -0.6(5) . . . . ?
C9 C2 C15 C16 134.0(3) . . . . ?
C9 C2 C15 C20 -53.9(4) . . . . ?
C9 C2 C21 C22 -160.6(3) . . . . ?
C9 C2 C21 C26 23.6(4) . . . . ?
C9 C10 C11 C12 0.9(5) . . . . ?
C10 C9 C14 C13 -0.9(5) . . . . ?
C10 C11 C12 N1 -177.5(3) . . . . ?
C10 C11 C12 C13 -1.5(5) . . . . ?
C11 C12 C13 C14 1.0(5) . . . . ?
C12 C13 C14 C9 0.2(5) . . . . ?
C14 C9 C10 C11 0.3(5) . . . . ?
C15 C2 C9 C10 -5.9(5) . . . . ?
C15 C2 C9 C14 177.8(3) . . . . ?
C15 C2 C21 C22 72.7(4) . . . . ?
C15 C2 C21 C26 -103.1(3) . . . . ?
C15 C16 C17 C18 -1.9(6) . . . . ?
C16 C15 C20 C19 -2.5(5) . . . . ?
C16 C17 C18 N2 178.1(3) . . . . ?
C16 C17 C18 C19 -0.5(5) . . . . ?
C17 C18 C19 C20 1.2(5) . . . . ?
C18 C19 C20 C15 0.3(6) . . . . ?
C20 C15 C16 C17 3.2(5) . . . . ?
C21 C2 C9 C10 -126.4(3) . . . . ?
C21 C2 C9 C14 57.4(4) . . . . ?
C21 C2 C15 C16 -102.5(4) . . . . ?
C21 C2 C15 C20 69.6(4) . . . . ?
C21 C22 C23 C24 0.5(6) . . . . ?
C22 C21 C26 C25 1.3(5) . . . . ?
C22 C23 C24 C25 1.2(7) . . . . ?
C23 C24 C25 C26 -1.6(6) . . . . ?
C24 C25 C26 C21 0.3(6) . . . . ?
C26 C21 C22 C23 -1.7(5) . . . . ?

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

data_Z-2NH2-TPE
_database_code_depnum_ccdc_archive 'CCDC 2120060'
loop_
_audit_author_name
_audit_author_address
lx
;Sichuan University
China
;
_audit_update_record             
;
2021-11-03 deposited with the CCDC.	2022-01-04 downloaded from the CCDC.
;
_audit_creation_date             2021-06-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C26 H22 N2'
_chemical_formula_sum            'C26 H22 N2'
_chemical_formula_weight         362.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3br1
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                   9.1427(9)
_cell_length_b                   10.2655(10)
_cell_length_c                   11.2401(11)
_cell_angle_alpha                76.016(8)
_cell_angle_beta                 84.388(8)
_cell_angle_gamma                76.867(9)
_cell_volume                     995.86(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1033
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.3080
_cell_measurement_theta_min      3.4010
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.1085
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7741
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_min         2.890
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   16.00   85.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -       17.5086   57.0000   30.0000 69

#__ type_ start__ end____ width___ exp.time_
  2 omega    3.00   68.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -       17.5086   57.0000  -30.0000 65

#__ type_ start__ end____ width___ exp.time_
  3 omega    1.00   87.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -       17.5086   38.0000 -150.0000 86

#__ type_ start__ end____ width___ exp.time_
  4 omega  -19.00   21.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.3211  -99.0000 -150.0000 40

#__ type_ start__ end____ width___ exp.time_
  5 omega    3.00   87.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -       17.5086   38.0000  120.0000 84

#__ type_ start__ end____ width___ exp.time_
  6 omega  -66.00  -39.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.3211 -178.0000  150.0000 27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0650577000
_diffrn_orient_matrix_UB_12      0.0281618000
_diffrn_orient_matrix_UB_13      -0.0057691000
_diffrn_orient_matrix_UB_21      -0.0457845000
_diffrn_orient_matrix_UB_22      0.0644745000
_diffrn_orient_matrix_UB_23      0.0047933000
_diffrn_orient_matrix_UB_31      0.0055550000
_diffrn_orient_matrix_UB_32      -0.0188692000
_diffrn_orient_matrix_UB_33      0.0646653000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1664
_reflns_number_total             4053
_reflns_odcompleteness_completeness 99.83
_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, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4053
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1747
_refine_ls_R_factor_gt           0.0611
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0327P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1460
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Rotating group:
 N1(H1A,H1B), N2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C16(H16), C17(H17), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24),
  C25(H25), C26(H26)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.0091(3) 0.2473(3) 0.4627(3) 0.0912(10) Uani 1 1 d . . . . .
H1A H 0.054906 0.162517 0.483343 0.109 Uiso 1 1 d GR . . . .
H1B H -0.037811 0.272355 0.526489 0.109 Uiso 1 1 d GR . . . .
N2 N 0.8311(3) -0.0451(3) 0.2315(3) 0.0944(10) Uani 1 1 d . . . . .
H2A H 0.788608 -0.095831 0.291371 0.113 Uiso 1 1 d GR . . . .
H2B H 0.820237 -0.066822 0.163818 0.113 Uiso 1 1 d GR . . . .
C1 C 0.4473(3) 0.5676(3) 0.2637(2) 0.0502(8) Uani 1 1 d . . . . .
C2 C 0.5775(3) 0.5213(3) 0.2051(2) 0.0518(8) Uani 1 1 d . . . . .
C3 C 0.3357(3) 0.4795(3) 0.3167(2) 0.0479(8) Uani 1 1 d . . . . .
C4 C 0.2758(3) 0.4741(3) 0.4359(3) 0.0536(8) Uani 1 1 d . . . . .
H4 H 0.308190 0.523431 0.483770 0.064 Uiso 1 1 calc R . . . .
C5 C 0.1696(3) 0.3975(3) 0.4848(3) 0.0574(9) Uani 1 1 d . . . . .
H5 H 0.133576 0.394016 0.565567 0.069 Uiso 1 1 calc R . . . .
C6 C 0.1163(3) 0.3264(3) 0.4159(3) 0.0570(9) Uani 1 1 d . . . . .
C7 C 0.1727(3) 0.3325(3) 0.2964(3) 0.0579(8) Uani 1 1 d . . . . .
H7 H 0.137075 0.285648 0.247999 0.069 Uiso 1 1 calc R . . . .
C8 C 0.2808(3) 0.4070(3) 0.2481(3) 0.0565(8) Uani 1 1 d . . . . .
H8 H 0.317882 0.408764 0.167839 0.068 Uiso 1 1 calc R . . . .
C9 C 0.4020(3) 0.7096(3) 0.2843(2) 0.0495(8) Uani 1 1 d . . . . .
C10 C 0.2564(4) 0.7869(3) 0.2658(3) 0.0636(9) Uani 1 1 d . . . . .
H10 H 0.186111 0.750687 0.236849 0.076 Uiso 1 1 calc R . . . .
C11 C 0.2145(4) 0.9168(4) 0.2898(3) 0.0789(11) Uani 1 1 d . . . . .
H11 H 0.117795 0.968284 0.274450 0.095 Uiso 1 1 calc R . . . .
C12 C 0.3152(5) 0.9690(4) 0.3361(3) 0.0825(12) Uani 1 1 d . . . . .
H12 H 0.286261 1.055185 0.354193 0.099 Uiso 1 1 calc R . . . .
C13 C 0.4579(5) 0.8954(4) 0.3558(3) 0.0768(11) Uani 1 1 d . . . . .
H13 H 0.526631 0.931789 0.386397 0.092 Uiso 1 1 calc R . . . .
C14 C 0.5008(4) 0.7667(3) 0.3304(3) 0.0611(9) Uani 1 1 d . . . . .
H14 H 0.598618 0.717270 0.344651 0.073 Uiso 1 1 calc R . . . .
C15 C 0.6362(3) 0.3718(3) 0.2110(3) 0.0502(8) Uani 1 1 d . . . . .
C16 C 0.6567(3) 0.2776(3) 0.3220(3) 0.0602(9) Uani 1 1 d . . . . .
H16 H 0.626958 0.307132 0.394299 0.072 Uiso 1 1 calc R . . . .
C17 C 0.7197(3) 0.1414(3) 0.3284(3) 0.0643(9) Uani 1 1 d . . . . .
H17 H 0.734047 0.080729 0.404499 0.077 Uiso 1 1 calc R . . . .
C18 C 0.7618(4) 0.0943(3) 0.2230(3) 0.0627(9) Uani 1 1 d . . . . .
C19 C 0.7424(3) 0.1855(4) 0.1115(3) 0.0649(9) Uani 1 1 d . . . . .
H19 H 0.770030 0.154705 0.039553 0.078 Uiso 1 1 calc R . . . .
C20 C 0.6820(3) 0.3225(3) 0.1057(3) 0.0592(9) Uani 1 1 d . . . . .
H20 H 0.671682 0.383504 0.029464 0.071 Uiso 1 1 calc R . . . .
C21 C 0.6756(4) 0.6141(3) 0.1341(3) 0.0522(8) Uani 1 1 d . . . . .
C22 C 0.6168(4) 0.7378(3) 0.0551(3) 0.0607(9) Uani 1 1 d . . . . .
H22 H 0.513290 0.765962 0.047955 0.073 Uiso 1 1 calc R . . . .
C23 C 0.7099(4) 0.8192(4) -0.0126(3) 0.0725(10) Uani 1 1 d . . . . .
H23 H 0.668810 0.901271 -0.065771 0.087 Uiso 1 1 calc R . . . .
C24 C 0.8622(5) 0.7806(4) -0.0026(3) 0.0787(11) Uani 1 1 d . . . . .
H24 H 0.924606 0.836477 -0.048061 0.094 Uiso 1 1 calc R . . . .
C25 C 0.9221(4) 0.6595(4) 0.0748(3) 0.0778(11) Uani 1 1 d . . . . .
H25 H 1.025771 0.633116 0.081783 0.093 Uiso 1 1 calc R . . . .
C26 C 0.8306(4) 0.5752(3) 0.1430(3) 0.0679(10) Uani 1 1 d . . . . .
H26 H 0.872993 0.492568 0.194799 0.081 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 H1A 0.8619 . ?
N1 H1B 0.8620 . ?
N1 C6 1.397(3) . ?
N2 H2A 0.8640 . ?
N2 H2B 0.8637 . ?
N2 C18 1.411(3) . ?
C1 C2 1.348(4) . ?
C1 C3 1.501(4) . ?
C1 C9 1.490(4) . ?
C2 C15 1.494(4) . ?
C2 C21 1.492(4) . ?
C3 C4 1.390(3) . ?
C3 C8 1.386(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.377(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.371(4) . ?
C6 C7 1.383(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.377(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.392(4) . ?
C9 C14 1.381(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.386(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.362(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.360(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.380(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.381(4) . ?
C15 C20 1.389(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.373(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.374(4) . ?
C18 C19 1.371(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.378(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.389(4) . ?
C21 C26 1.389(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.375(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.367(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.365(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.385(4) . ?
C26 H26 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
H1A N1 H1B 109.2 . . ?
C6 N1 H1A 108.3 . . ?
C6 N1 H1B 110.0 . . ?
H2A N2 H2B 109.1 . . ?
C18 N2 H2A 109.6 . . ?
C18 N2 H2B 108.9 . . ?
C2 C1 C3 123.0(3) . . ?
C2 C1 C9 123.3(3) . . ?
C9 C1 C3 113.7(2) . . ?
C1 C2 C15 121.8(3) . . ?
C1 C2 C21 122.9(3) . . ?
C21 C2 C15 115.4(3) . . ?
C4 C3 C1 120.7(3) . . ?
C8 C3 C1 122.3(2) . . ?
C8 C3 C4 116.9(3) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 C3 121.6(3) . . ?
C5 C4 H4 119.2 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 N1 122.3(3) . . ?
C5 C6 C7 118.4(3) . . ?
C7 C6 N1 119.3(3) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 C6 120.8(3) . . ?
C8 C7 H7 119.6 . . ?
C3 C8 H8 119.3 . . ?
C7 C8 C3 121.4(3) . . ?
C7 C8 H8 119.3 . . ?
C10 C9 C1 121.8(3) . . ?
C14 C9 C1 120.9(3) . . ?
C14 C9 C10 117.1(3) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.1(3) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 119.9(4) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.2(4) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.1(4) . . ?
C14 C13 H13 119.9 . . ?
C9 C14 H14 119.2 . . ?
C13 C14 C9 121.5(3) . . ?
C13 C14 H14 119.2 . . ?
C16 C15 C2 121.4(3) . . ?
C16 C15 C20 116.9(3) . . ?
C20 C15 C2 121.6(3) . . ?
C15 C16 H16 119.1 . . ?
C17 C16 C15 121.7(3) . . ?
C17 C16 H16 119.1 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.4(3) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 N2 119.6(3) . . ?
C19 C18 N2 121.2(3) . . ?
C19 C18 C17 119.1(3) . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.2(3) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 H20 119.2 . . ?
C19 C20 C15 121.6(3) . . ?
C19 C20 H20 119.2 . . ?
C22 C21 C2 121.8(3) . . ?
C22 C21 C26 118.2(3) . . ?
C26 C21 C2 119.9(3) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 C21 120.7(3) . . ?
C23 C22 H22 119.6 . . ?
C22 C23 H23 119.7 . . ?
C24 C23 C22 120.7(3) . . ?
C24 C23 H23 119.7 . . ?
C23 C24 H24 120.3 . . ?
C25 C24 C23 119.5(3) . . ?
C25 C24 H24 120.3 . . ?
C24 C25 H25 119.6 . . ?
C24 C25 C26 120.9(3) . . ?
C26 C25 H25 119.6 . . ?
C21 C26 H26 120.0 . . ?
C25 C26 C21 120.1(3) . . ?
C25 C26 H26 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C6 C7 C8 -178.6(3) . . . . ?
N2 C18 C19 C20 -176.4(3) . . . . ?
C1 C2 C15 C16 -54.4(4) . . . . ?
C1 C2 C15 C20 130.0(3) . . . . ?
C1 C2 C21 C22 -44.0(4) . . . . ?
C1 C2 C21 C26 138.2(3) . . . . ?
C1 C3 C4 C5 177.8(3) . . . . ?
C1 C3 C8 C7 -176.6(3) . . . . ?
C1 C9 C10 C11 177.5(3) . . . . ?
C1 C9 C14 C13 -176.6(3) . . . . ?
C2 C1 C3 C4 131.6(3) . . . . ?
C2 C1 C3 C8 -52.4(4) . . . . ?
C2 C1 C9 C10 136.3(3) . . . . ?
C2 C1 C9 C14 -48.0(4) . . . . ?
C2 C15 C16 C17 -175.6(3) . . . . ?
C2 C15 C20 C19 177.0(3) . . . . ?
C2 C21 C22 C23 -177.7(3) . . . . ?
C2 C21 C26 C25 178.3(3) . . . . ?
C3 C1 C2 C15 -13.1(4) . . . . ?
C3 C1 C2 C21 169.2(3) . . . . ?
C3 C1 C9 C10 -44.9(3) . . . . ?
C3 C1 C9 C14 130.8(3) . . . . ?
C3 C4 C5 C6 -1.7(4) . . . . ?
C4 C3 C8 C7 -0.4(4) . . . . ?
C4 C5 C6 N1 179.7(3) . . . . ?
C4 C5 C6 C7 0.5(5) . . . . ?
C5 C6 C7 C8 0.7(4) . . . . ?
C6 C7 C8 C3 -0.7(5) . . . . ?
C8 C3 C4 C5 1.6(4) . . . . ?
C9 C1 C2 C15 165.6(3) . . . . ?
C9 C1 C2 C21 -12.1(4) . . . . ?
C9 C1 C3 C4 -47.3(4) . . . . ?
C9 C1 C3 C8 128.8(3) . . . . ?
C9 C10 C11 C12 -2.1(5) . . . . ?
C10 C9 C14 C13 -0.7(4) . . . . ?
C10 C11 C12 C13 1.7(5) . . . . ?
C11 C12 C13 C14 -0.8(5) . . . . ?
C12 C13 C14 C9 0.3(5) . . . . ?
C14 C9 C10 C11 1.6(4) . . . . ?
C15 C2 C21 C22 138.1(3) . . . . ?
C15 C2 C21 C26 -39.7(4) . . . . ?
C15 C16 C17 C18 -1.4(5) . . . . ?
C16 C15 C20 C19 1.3(5) . . . . ?
C16 C17 C18 N2 177.9(3) . . . . ?
C16 C17 C18 C19 1.1(5) . . . . ?
C17 C18 C19 C20 0.3(5) . . . . ?
C18 C19 C20 C15 -1.5(5) . . . . ?
C20 C15 C16 C17 0.2(5) . . . . ?
C21 C2 C15 C16 123.5(3) . . . . ?
C21 C2 C15 C20 -52.1(4) . . . . ?
C21 C22 C23 C24 -0.7(5) . . . . ?
C22 C21 C26 C25 0.4(5) . . . . ?
C22 C23 C24 C25 0.6(5) . . . . ?
C23 C24 C25 C26 0.1(5) . . . . ?
C24 C25 C26 C21 -0.6(5) . . . . ?
C26 C21 C22 C23 0.2(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
