# Electronic Supplementary Material (ESI) for Materials Horizons.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_s
_database_code_depnum_ccdc_archive 'CCDC 1975855'
loop_
_audit_author_name
_audit_author_address
'Yi-Zhong Shi'
;Soochow University
China
;
_audit_update_record             
;
2020-01-07 deposited with the CCDC.	2020-08-11 downloaded from the CCDC.
;
_audit_creation_date             2020-01-07
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
"10-(4-([2,2':6',2''-terpyridin]-4'-yl) phenyl)-10H-phenoxazine"
_chemical_formula_moiety         'C33 H22 N4 O'
_chemical_formula_sum            'C33 H22 N4 O'
_chemical_formula_weight         490.55
_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 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.3137(11)
_cell_length_b                   19.520(2)
_cell_length_c                   13.6482(16)
_cell_angle_alpha                90
_cell_angle_beta                 94.300(2)
_cell_angle_gamma                90
_cell_volume                     2474.3(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1758
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.849
_cell_measurement_theta_min      2.765
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_unetI/netI     0.0657
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16052
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.554
_diffrn_reflns_theta_min         1.824
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2694
_reflns_number_total             5696
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         5696
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1313
_refine_ls_R_factor_gt           0.0520
_refine_ls_restrained_S_all      0.981
_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)+(0.0569P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1381
_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:
 C2(H2), C4(H4), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13),
 C14(H14), C15(H15), C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24),
  C25(H25), C26(H26), C29(H29), C30(H30), C31(H31), C32(H32)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.07094(17) 0.12138(8) -0.59677(10) 0.0677(5) Uani 1 1 d . . . . .
N1 N -0.76016(17) 0.04110(8) 0.04304(11) 0.0496(4) Uani 1 1 d . . . . .
N2 N -0.23074(18) 0.11470(9) -0.43103(11) 0.0580(5) Uani 1 1 d . . . . .
N3 N -0.6926(2) 0.22068(9) 0.07925(14) 0.0712(6) Uani 1 1 d . . . . .
N4 N -0.7459(2) -0.13078(9) -0.04889(13) 0.0708(6) Uani 1 1 d . . . . .
C1 C -0.7041(2) 0.10311(10) 0.02858(13) 0.0477(5) Uani 1 1 d . . . . .
C2 C -0.6158(2) 0.11652(10) -0.04691(14) 0.0506(5) Uani 1 1 d . . . . .
H2 H -0.578878 0.160308 -0.054410 0.061 Uiso 1 1 calc R U . . .
C3 C -0.5826(2) 0.06455(10) -0.11129(13) 0.0467(5) Uani 1 1 d . . . . .
C4 C -0.6410(2) 0.00026(10) -0.09529(13) 0.0485(5) Uani 1 1 d . . . . .
H4 H -0.621523 -0.036235 -0.136043 0.058 Uiso 1 1 calc R U . . .
C5 C -0.7287(2) -0.00936(10) -0.01810(13) 0.0472(5) Uani 1 1 d . . . . .
C6 C -0.7952(2) -0.07725(10) -0.00053(13) 0.0504(5) Uani 1 1 d . . . . .
C7 C -0.9035(2) -0.08340(12) 0.06271(15) 0.0624(6) Uani 1 1 d . . . . .
H7 H -0.936906 -0.045130 0.094619 0.075 Uiso 1 1 calc R U . . .
C8 C -0.9611(3) -0.14703(14) 0.07769(18) 0.0759(7) Uani 1 1 d . . . . .
H8 H -1.033584 -0.152349 0.120357 0.091 Uiso 1 1 calc R U . . .
C9 C -0.9112(3) -0.20210(13) 0.02970(18) 0.0780(7) Uani 1 1 d . . . . .
H9 H -0.948626 -0.245619 0.038778 0.094 Uiso 1 1 calc R U . . .
C10 C -0.8044(3) -0.19175(13) -0.03243(18) 0.0827(8) Uani 1 1 d . . . . .
H10 H -0.770492 -0.229554 -0.065171 0.099 Uiso 1 1 calc R U . . .
C11 C -0.7435(2) 0.15799(11) 0.09643(14) 0.0513(5) Uani 1 1 d . . . . .
C12 C -0.8296(2) 0.14525(12) 0.17267(15) 0.0653(6) Uani 1 1 d . . . . .
H12 H -0.863253 0.101231 0.183364 0.078 Uiso 1 1 calc R U . . .
C13 C -0.8648(3) 0.19849(14) 0.23262(17) 0.0788(8) Uani 1 1 d . . . . .
H13 H -0.922342 0.190882 0.284378 0.095 Uiso 1 1 calc R U . . .
C14 C -0.8140(3) 0.26271(14) 0.21491(18) 0.0835(8) Uani 1 1 d . . . . .
H14 H -0.836783 0.299692 0.253803 0.100 Uiso 1 1 calc R U . . .
C15 C -0.7286(3) 0.27104(13) 0.13835(18) 0.0872(9) Uani 1 1 d . . . . .
H15 H -0.693653 0.314713 0.126911 0.105 Uiso 1 1 calc R U . . .
C16 C -0.4887(2) 0.07738(10) -0.19345(13) 0.0455(5) Uani 1 1 d . . . . .
C17 C -0.4641(2) 0.02712(12) -0.26105(16) 0.0683(7) Uani 1 1 d . . . . .
H17 H -0.504298 -0.016059 -0.254116 0.082 Uiso 1 1 calc R U . . .
C18 C -0.3805(3) 0.03955(12) -0.33943(17) 0.0719(7) Uani 1 1 d . . . . .
H18 H -0.367388 0.005112 -0.384990 0.086 Uiso 1 1 calc R U . . .
C19 C -0.3177(2) 0.10207(11) -0.34984(14) 0.0534(5) Uani 1 1 d . . . . .
C20 C -0.3381(3) 0.15218(12) -0.28252(15) 0.0667(7) Uani 1 1 d . . . . .
H20 H -0.294428 0.194699 -0.288282 0.080 Uiso 1 1 calc R U . . .
C21 C -0.4238(3) 0.13982(11) -0.20548(15) 0.0646(6) Uani 1 1 d . . . . .
H21 H -0.437705 0.174705 -0.160764 0.078 Uiso 1 1 calc R U . . .
C22 C -0.0867(2) 0.09287(10) -0.42500(14) 0.0492(5) Uani 1 1 d . . . . .
C23 C -0.0172(2) 0.06741(11) -0.33977(16) 0.0606(6) Uani 1 1 d . . . . .
H23 H -0.066431 0.063947 -0.283186 0.073 Uiso 1 1 calc R U . . .
C24 C 0.1258(3) 0.04694(12) -0.33794(18) 0.0707(6) Uani 1 1 d . . . . .
H24 H 0.171705 0.029933 -0.280126 0.085 Uiso 1 1 calc R U . . .
C25 C 0.1999(3) 0.05166(12) -0.4211(2) 0.0739(7) Uani 1 1 d . . . . .
H25 H 0.295760 0.038080 -0.419631 0.089 Uiso 1 1 calc R U . . .
C26 C 0.1318(2) 0.07648(11) -0.50616(18) 0.0639(6) Uani 1 1 d . . . . .
H26 H 0.181496 0.079708 -0.562584 0.077 Uiso 1 1 calc R U . . .
C27 C -0.0092(2) 0.09655(10) -0.50846(15) 0.0513(5) Uani 1 1 d . . . . .
C28 C -0.2987(2) 0.13023(10) -0.52358(14) 0.0508(5) Uani 1 1 d . . . . .
C29 C -0.4435(2) 0.14559(12) -0.53828(17) 0.0679(6) Uani 1 1 d . . . . .
H29 H -0.500470 0.144984 -0.485145 0.081 Uiso 1 1 calc R U . . .
C30 C -0.5050(3) 0.16180(13) -0.6303(2) 0.0822(7) Uani 1 1 d . . . . .
H30 H -0.602433 0.172611 -0.638613 0.099 Uiso 1 1 calc R U . . .
C31 C -0.4233(3) 0.16205(13) -0.70980(18) 0.0815(7) Uani 1 1 d . . . . .
H31 H -0.465177 0.172307 -0.772068 0.098 Uiso 1 1 calc R U . . .
C32 C -0.2795(3) 0.14708(11) -0.69678(16) 0.0688(7) Uani 1 1 d . . . . .
H32 H -0.223505 0.147134 -0.750391 0.083 Uiso 1 1 calc R U . . .
C33 C -0.2180(2) 0.13206(10) -0.60511(15) 0.0526(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C27 1.384(3) . ?
O1 C33 1.382(2) . ?
N1 C1 1.339(2) . ?
N1 C5 1.337(2) . ?
N2 C19 1.442(2) . ?
N2 C22 1.404(2) . ?
N2 C28 1.403(2) . ?
N3 C11 1.340(2) . ?
N3 C15 1.331(3) . ?
N4 C6 1.336(2) . ?
N4 C10 1.335(3) . ?
C1 C2 1.391(2) . ?
C1 C11 1.480(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.392(2) . ?
C3 C4 1.392(3) . ?
C3 C16 1.494(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.393(2) . ?
C5 C6 1.490(3) . ?
C6 C7 1.381(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.374(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.359(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.370(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.383(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.377(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.368(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.369(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.377(3) . ?
C16 C21 1.376(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.391(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.365(3) . ?
C19 C20 1.365(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.388(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.381(3) . ?
C22 C27 1.395(2) . ?
C23 H23 0.9300 . ?
C23 C24 1.389(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.375(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.369(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.368(3) . ?
C28 C29 1.382(3) . ?
C28 C33 1.389(3) . ?
C29 H29 0.9300 . ?
C29 C30 1.378(3) . ?
C30 H30 0.9300 . ?
C30 C31 1.371(3) . ?
C31 H31 0.9300 . ?
C31 C32 1.369(3) . ?
C32 H32 0.9300 . ?
C32 C33 1.368(3) . ?

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
C33 O1 C27 117.98(14) . . ?
C5 N1 C1 117.91(15) . . ?
C22 N2 C19 119.48(16) . . ?
C28 N2 C19 119.17(17) . . ?
C28 N2 C22 118.89(15) . . ?
C15 N3 C11 117.38(18) . . ?
C10 N4 C6 117.04(19) . . ?
N1 C1 C2 122.56(18) . . ?
N1 C1 C11 116.40(16) . . ?
C2 C1 C11 121.04(18) . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.17(18) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 C16 121.47(17) . . ?
C4 C3 C2 116.75(16) . . ?
C4 C3 C16 121.78(17) . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.90(18) . . ?
C5 C4 H4 120.1 . . ?
N1 C5 C4 122.72(18) . . ?
N1 C5 C6 116.21(16) . . ?
C4 C5 C6 121.06(18) . . ?
N4 C6 C5 117.00(17) . . ?
N4 C6 C7 122.36(19) . . ?
C7 C6 C5 120.65(19) . . ?
C6 C7 H7 120.6 . . ?
C8 C7 C6 118.9(2) . . ?
C8 C7 H7 120.6 . . ?
C7 C8 H8 120.3 . . ?
C9 C8 C7 119.5(2) . . ?
C9 C8 H8 120.3 . . ?
C8 C9 H9 120.9 . . ?
C8 C9 C10 118.2(2) . . ?
C10 C9 H9 120.9 . . ?
N4 C10 C9 124.1(2) . . ?
N4 C10 H10 118.0 . . ?
C9 C10 H10 118.0 . . ?
N3 C11 C1 116.35(16) . . ?
N3 C11 C12 121.94(19) . . ?
C12 C11 C1 121.70(19) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 C11 119.3(2) . . ?
C13 C12 H12 120.4 . . ?
C12 C13 H13 120.5 . . ?
C14 C13 C12 119.0(2) . . ?
C14 C13 H13 120.5 . . ?
C13 C14 H14 120.9 . . ?
C13 C14 C15 118.2(2) . . ?
C15 C14 H14 120.9 . . ?
N3 C15 C14 124.2(2) . . ?
N3 C15 H15 117.9 . . ?
C14 C15 H15 117.9 . . ?
C17 C16 C3 121.29(18) . . ?
C21 C16 C3 121.68(17) . . ?
C21 C16 C17 117.03(16) . . ?
C16 C17 H17 119.3 . . ?
C16 C17 C18 121.4(2) . . ?
C18 C17 H17 119.3 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.3(2) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 N2 120.17(19) . . ?
C20 C19 N2 120.61(19) . . ?
C20 C19 C18 119.22(17) . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.1(2) . . ?
C21 C20 H20 119.9 . . ?
C16 C21 C20 121.81(19) . . ?
C16 C21 H21 119.1 . . ?
C20 C21 H21 119.1 . . ?
C23 C22 N2 122.98(16) . . ?
C23 C22 C27 117.89(19) . . ?
C27 C22 N2 119.14(19) . . ?
C22 C23 H23 119.8 . . ?
C22 C23 C24 120.48(19) . . ?
C24 C23 H23 119.8 . . ?
C23 C24 H24 119.8 . . ?
C25 C24 C23 120.4(2) . . ?
C25 C24 H24 119.8 . . ?
C24 C25 H25 120.2 . . ?
C26 C25 C24 119.6(2) . . ?
C26 C25 H25 120.2 . . ?
C25 C26 H26 119.9 . . ?
C27 C26 C25 120.3(2) . . ?
C27 C26 H26 119.9 . . ?
O1 C27 C22 121.51(18) . . ?
C26 C27 O1 117.11(18) . . ?
C26 C27 C22 121.4(2) . . ?
C29 C28 N2 123.19(17) . . ?
C29 C28 C33 117.3(2) . . ?
C33 C28 N2 119.47(19) . . ?
C28 C29 H29 119.4 . . ?
C30 C29 C28 121.1(2) . . ?
C30 C29 H29 119.4 . . ?
C29 C30 H30 119.8 . . ?
C31 C30 C29 120.3(2) . . ?
C31 C30 H30 119.8 . . ?
C30 C31 H31 120.3 . . ?
C32 C31 C30 119.5(2) . . ?
C32 C31 H31 120.3 . . ?
C31 C32 H32 119.9 . . ?
C33 C32 C31 120.2(2) . . ?
C33 C32 H32 119.9 . . ?
O1 C33 C28 121.51(19) . . ?
C32 C33 O1 116.87(19) . . ?
C32 C33 C28 121.6(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 0.1(3) . . . . ?
N1 C1 C11 N3 -177.18(19) . . . . ?
N1 C1 C11 C12 2.1(3) . . . . ?
N1 C5 C6 N4 -168.52(18) . . . . ?
N1 C5 C6 C7 11.9(3) . . . . ?
N2 C19 C20 C21 179.0(2) . . . . ?
N2 C22 C23 C24 -179.62(19) . . . . ?
N2 C22 C27 O1 0.2(3) . . . . ?
N2 C22 C27 C26 179.42(19) . . . . ?
N2 C28 C29 C30 178.8(2) . . . . ?
N2 C28 C33 O1 -2.4(3) . . . . ?
N2 C28 C33 C32 -179.87(19) . . . . ?
N3 C11 C12 C13 0.3(3) . . . . ?
N4 C6 C7 C8 1.1(3) . . . . ?
C1 N1 C5 C4 0.0(3) . . . . ?
C1 N1 C5 C6 -179.00(17) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C1 C2 C3 C16 179.68(18) . . . . ?
C1 C11 C12 C13 -178.9(2) . . . . ?
C2 C1 C11 N3 1.6(3) . . . . ?
C2 C1 C11 C12 -179.1(2) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C2 C3 C16 C17 -175.4(2) . . . . ?
C2 C3 C16 C21 4.1(3) . . . . ?
C3 C4 C5 N1 -0.2(3) . . . . ?
C3 C4 C5 C6 178.70(18) . . . . ?
C3 C16 C17 C18 177.9(2) . . . . ?
C3 C16 C21 C20 -179.1(2) . . . . ?
C4 C3 C16 C17 4.6(3) . . . . ?
C4 C3 C16 C21 -175.9(2) . . . . ?
C4 C5 C6 N4 12.5(3) . . . . ?
C4 C5 C6 C7 -167.09(19) . . . . ?
C5 N1 C1 C2 0.1(3) . . . . ?
C5 N1 C1 C11 178.84(17) . . . . ?
C5 C6 C7 C8 -179.4(2) . . . . ?
C6 N4 C10 C9 0.6(4) . . . . ?
C6 C7 C8 C9 -0.5(4) . . . . ?
C7 C8 C9 C10 0.0(4) . . . . ?
C8 C9 C10 N4 0.0(4) . . . . ?
C10 N4 C6 C5 179.3(2) . . . . ?
C10 N4 C6 C7 -1.1(3) . . . . ?
C11 N3 C15 C14 0.0(4) . . . . ?
C11 C1 C2 C3 -178.58(18) . . . . ?
C11 C12 C13 C14 0.2(4) . . . . ?
C12 C13 C14 C15 -0.6(4) . . . . ?
C13 C14 C15 N3 0.5(4) . . . . ?
C15 N3 C11 C1 178.9(2) . . . . ?
C15 N3 C11 C12 -0.4(3) . . . . ?
C16 C3 C4 C5 -179.64(18) . . . . ?
C16 C17 C18 C19 1.5(4) . . . . ?
C17 C16 C21 C20 0.5(3) . . . . ?
C17 C18 C19 N2 179.8(2) . . . . ?
C17 C18 C19 C20 -0.1(4) . . . . ?
C18 C19 C20 C21 -1.1(4) . . . . ?
C19 N2 C22 C23 -8.6(3) . . . . ?
C19 N2 C22 C27 171.12(19) . . . . ?
C19 N2 C28 C29 11.4(3) . . . . ?
C19 N2 C28 C33 -170.13(18) . . . . ?
C19 C20 C21 C16 0.9(4) . . . . ?
C21 C16 C17 C18 -1.7(3) . . . . ?
C22 N2 C19 C18 -81.6(3) . . . . ?
C22 N2 C19 C20 98.3(2) . . . . ?
C22 N2 C28 C29 173.5(2) . . . . ?
C22 N2 C28 C33 -8.0(3) . . . . ?
C22 C23 C24 C25 -0.1(3) . . . . ?
C23 C22 C27 O1 179.96(18) . . . . ?
C23 C22 C27 C26 -0.8(3) . . . . ?
C23 C24 C25 C26 -0.2(3) . . . . ?
C24 C25 C26 C27 0.1(3) . . . . ?
C25 C26 C27 O1 179.7(2) . . . . ?
C25 C26 C27 C22 0.5(3) . . . . ?
C27 O1 C33 C28 11.6(3) . . . . ?
C27 O1 C33 C32 -170.87(18) . . . . ?
C27 C22 C23 C24 0.6(3) . . . . ?
C28 N2 C19 C18 80.4(3) . . . . ?
C28 N2 C19 C20 -99.7(3) . . . . ?
C28 N2 C22 C23 -170.67(19) . . . . ?
C28 N2 C22 C27 9.1(3) . . . . ?
C28 C29 C30 C31 0.9(4) . . . . ?
C29 C28 C33 O1 176.17(19) . . . . ?
C29 C28 C33 C32 -1.3(3) . . . . ?
C29 C30 C31 C32 -1.0(4) . . . . ?
C30 C31 C32 C33 -0.1(4) . . . . ?
C31 C32 C33 O1 -176.4(2) . . . . ?
C31 C32 C33 C28 1.2(3) . . . . ?
C33 O1 C27 C22 -10.4(3) . . . . ?
C33 O1 C27 C26 170.31(18) . . . . ?
C33 C28 C29 C30 0.2(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_s_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1975857'
loop_
_audit_author_name
_audit_author_address
'Yi-Zhong Shi'
;Soochow University
China
;
_audit_update_record             
;
2020-01-07 deposited with the CCDC.	2020-08-11 downloaded from the CCDC.
;
_audit_creation_date             2020-01-07
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
"10-(4-([4,2':6',4''-terpyridin]-4'-yl) phenyl)-10H-phenoxazine"
_chemical_formula_moiety         'C33 H22 N4 O'
_chemical_formula_sum            'C33 H22 N4 O'
_chemical_formula_weight         490.55
_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 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 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      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                   9.449(3)
_cell_length_b                   10.758(3)
_cell_length_c                   13.327(4)
_cell_angle_alpha                96.653(6)
_cell_angle_beta                 98.071(6)
_cell_angle_gamma                112.124(6)
_cell_volume                     1221.3(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    666
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.165
_cell_measurement_theta_min      2.364
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0861
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6784
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_min         1.570
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1883
_reflns_number_total             4461
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.896
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4461
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1670
_refine_ls_R_factor_gt           0.0600
_refine_ls_restrained_S_all      0.896
_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)+(0.0717P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1312
_refine_ls_wR_factor_ref         0.1638
_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:
 C2(H2), C4(H4), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12),
 C14(H14), C15(H15), C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24),
  C25(H25), C26(H26), C29(H29), C30(H30), C31(H31), C32(H32)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0201(3) 0.9732(3) 0.6659(2) 0.0854(8) Uani 1 1 d . . . . .
N1 N 0.2469(3) 0.3701(3) 0.00025(19) 0.0542(7) Uani 1 1 d . . . . .
N2 N 0.0804(3) 0.8053(3) 0.51623(19) 0.0602(8) Uani 1 1 d . . . . .
N3 N 0.3556(4) 0.6655(4) -0.2673(2) 0.0897(11) Uani 1 1 d . . . . .
N4 N 0.1927(5) -0.0963(4) 0.0620(3) 0.0873(10) Uani 1 1 d . . . . .
C1 C 0.2485(3) 0.4961(3) 0.0017(2) 0.0490(8) Uani 1 1 d . . . . .
C2 C 0.2201(3) 0.5666(3) 0.0853(2) 0.0512(8) Uani 1 1 d . . . . .
H2 H 0.222691 0.653581 0.083575 0.061 Uiso 1 1 calc R U . . .
C3 C 0.1878(3) 0.5079(3) 0.1715(2) 0.0476(8) Uani 1 1 d . . . . .
C4 C 0.1841(4) 0.3782(3) 0.1685(2) 0.0550(9) Uani 1 1 d . . . . .
H4 H 0.161656 0.334684 0.224195 0.066 Uiso 1 1 calc R U . . .
C5 C 0.2137(4) 0.3116(3) 0.0829(2) 0.0510(8) Uani 1 1 d . . . . .
C6 C 0.2718(5) 0.7053(5) -0.2079(3) 0.0910(13) Uani 1 1 d . . . . .
H6 H 0.235582 0.770306 -0.226702 0.109 Uiso 1 1 calc R U . . .
C7 C 0.2366(4) 0.6543(4) -0.1199(3) 0.0707(11) Uani 1 1 d . . . . .
H7 H 0.179624 0.686521 -0.080416 0.085 Uiso 1 1 calc R U . . .
C8 C 0.2853(3) 0.5560(3) -0.0904(2) 0.0510(8) Uani 1 1 d . . . . .
C9 C 0.3715(4) 0.5144(4) -0.1517(3) 0.0655(10) Uani 1 1 d . . . . .
H9 H 0.405987 0.447130 -0.136312 0.079 Uiso 1 1 calc R U . . .
C10 C 0.4059(5) 0.5752(5) -0.2373(3) 0.0796(12) Uani 1 1 d . . . . .
H10 H 0.468816 0.549745 -0.275602 0.096 Uiso 1 1 calc R U . . .
C11 C 0.2922(5) -0.0051(5) 0.0207(4) 0.0926(13) Uani 1 1 d . . . . .
H11 H 0.358941 -0.031502 -0.013057 0.111 Uiso 1 1 calc R U . . .
C12 C 0.3046(4) 0.1302(4) 0.0241(3) 0.0780(11) Uani 1 1 d . . . . .
H12 H 0.374619 0.189719 -0.008607 0.094 Uiso 1 1 calc R U . . .
C13 C 0.2100(4) 0.1721(4) 0.0775(2) 0.0582(9) Uani 1 1 d . . . . .
C14 C 0.1078(4) 0.0761(4) 0.1228(3) 0.0692(10) Uani 1 1 d . . . . .
H14 H 0.042753 0.099417 0.160363 0.083 Uiso 1 1 calc R U . . .
C15 C 0.1035(5) -0.0541(4) 0.1117(3) 0.0800(12) Uani 1 1 d . . . . .
H15 H 0.032239 -0.116972 0.141611 0.096 Uiso 1 1 calc R U . . .
C16 C 0.1594(3) 0.5824(3) 0.2617(2) 0.0473(8) Uani 1 1 d . . . . .
C17 C 0.1966(4) 0.5611(4) 0.3609(2) 0.0605(9) Uani 1 1 d . . . . .
H17 H 0.239124 0.497476 0.371585 0.073 Uiso 1 1 calc R U . . .
C18 C 0.1709(4) 0.6341(4) 0.4444(2) 0.0617(9) Uani 1 1 d . . . . .
H18 H 0.195684 0.618025 0.510338 0.074 Uiso 1 1 calc R U . . .
C19 C 0.1095(4) 0.7295(3) 0.4311(2) 0.0518(8) Uani 1 1 d . . . . .
C20 C 0.0710(4) 0.7500(4) 0.3324(2) 0.0624(10) Uani 1 1 d . . . . .
H20 H 0.028407 0.813641 0.321934 0.075 Uiso 1 1 calc R U . . .
C21 C 0.0951(4) 0.6771(3) 0.2491(2) 0.0581(9) Uani 1 1 d . . . . .
H21 H 0.067516 0.691867 0.183156 0.070 Uiso 1 1 calc R U . . .
C22 C -0.0732(4) 0.7814(3) 0.5255(2) 0.0520(8) Uani 1 1 d . . . . .
C23 C -0.2008(4) 0.6751(4) 0.4634(3) 0.0710(11) Uani 1 1 d . . . . .
H23 H -0.186170 0.617054 0.412317 0.085 Uiso 1 1 calc R U . . .
C24 C -0.3494(4) 0.6543(5) 0.4766(3) 0.0855(13) Uani 1 1 d . . . . .
H24 H -0.434399 0.583623 0.433338 0.103 Uiso 1 1 calc R U . . .
C25 C -0.3733(4) 0.7358(5) 0.5521(3) 0.0845(13) Uani 1 1 d . . . . .
H25 H -0.473752 0.719271 0.562063 0.101 Uiso 1 1 calc R U . . .
C26 C -0.2493(5) 0.8416(4) 0.6128(3) 0.0759(11) Uani 1 1 d . . . . .
H26 H -0.265176 0.899333 0.663386 0.091 Uiso 1 1 calc R U . . .
C27 C -0.1007(4) 0.8639(4) 0.6000(2) 0.0588(9) Uani 1 1 d . . . . .
C28 C 0.2037(4) 0.9104(3) 0.5871(2) 0.0520(8) Uani 1 1 d . . . . .
C29 C 0.3578(4) 0.9392(4) 0.5876(3) 0.0781(11) Uani 1 1 d . . . . .
H29 H 0.384645 0.887824 0.538629 0.094 Uiso 1 1 calc R U . . .
C30 C 0.4747(5) 1.0436(5) 0.6597(3) 0.0998(15) Uani 1 1 d . . . . .
H30 H 0.578619 1.060970 0.658885 0.120 Uiso 1 1 calc R U . . .
C31 C 0.4384(5) 1.1208(5) 0.7317(3) 0.1061(16) Uani 1 1 d . . . . .
H31 H 0.516716 1.191961 0.779302 0.127 Uiso 1 1 calc R U . . .
C32 C 0.2843(5) 1.0921(4) 0.7329(3) 0.0842(12) Uani 1 1 d . . . . .
H32 H 0.257458 1.142157 0.782819 0.101 Uiso 1 1 calc R U . . .
C33 C 0.1712(4) 0.9906(4) 0.6612(2) 0.0567(9) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C27 1.387(4) . ?
O1 C33 1.380(4) . ?
N1 C1 1.347(4) . ?
N1 C5 1.349(4) . ?
N2 C19 1.439(4) . ?
N2 C22 1.402(4) . ?
N2 C28 1.407(4) . ?
N3 C6 1.338(5) . ?
N3 C10 1.309(5) . ?
N4 C11 1.313(5) . ?
N4 C15 1.316(4) . ?
C1 C2 1.389(4) . ?
C1 C8 1.476(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.390(4) . ?
C3 C4 1.378(4) . ?
C3 C16 1.479(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.394(4) . ?
C5 C13 1.481(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.381(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.378(4) . ?
C8 C9 1.382(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.397(5) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.410(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.384(4) . ?
C13 C14 1.386(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.375(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.387(4) . ?
C16 C21 1.382(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.390(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.373(4) . ?
C19 C20 1.379(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.380(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.381(5) . ?
C22 C27 1.373(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.377(5) . ?
C24 H24 0.9300 . ?
C24 C25 1.355(5) . ?
C25 H25 0.9300 . ?
C25 C26 1.356(5) . ?
C26 H26 0.9300 . ?
C26 C27 1.372(4) . ?
C28 C29 1.368(4) . ?
C28 C33 1.378(4) . ?
C29 H29 0.9300 . ?
C29 C30 1.386(5) . ?
C30 H30 0.9300 . ?
C30 C31 1.360(5) . ?
C31 H31 0.9300 . ?
C31 C32 1.373(5) . ?
C32 H32 0.9300 . ?
C32 C33 1.356(5) . ?

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
C33 O1 C27 118.2(3) . . ?
C1 N1 C5 117.7(3) . . ?
C22 N2 C19 119.9(3) . . ?
C22 N2 C28 118.8(3) . . ?
C28 N2 C19 121.1(3) . . ?
C10 N3 C6 116.5(3) . . ?
C11 N4 C15 116.1(4) . . ?
N1 C1 C2 122.3(3) . . ?
N1 C1 C8 115.8(3) . . ?
C2 C1 C8 121.8(3) . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.4(3) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 C16 121.1(3) . . ?
C4 C3 C2 116.8(3) . . ?
C4 C3 C16 122.1(3) . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.7(3) . . ?
C5 C4 H4 119.6 . . ?
N1 C5 C4 122.0(3) . . ?
N1 C5 C13 116.1(3) . . ?
C4 C5 C13 121.9(3) . . ?
N3 C6 H6 118.5 . . ?
N3 C6 C7 123.0(4) . . ?
C7 C6 H6 118.5 . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.4(4) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 C1 122.7(3) . . ?
C7 C8 C9 116.7(3) . . ?
C9 C8 C1 120.6(3) . . ?
C8 C9 H9 120.6 . . ?
C8 C9 C10 118.8(4) . . ?
C10 C9 H9 120.6 . . ?
N3 C10 C9 124.5(4) . . ?
N3 C10 H10 117.7 . . ?
C9 C10 H10 117.7 . . ?
N4 C11 H11 117.8 . . ?
N4 C11 C12 124.3(4) . . ?
C12 C11 H11 117.8 . . ?
C11 C12 H12 120.8 . . ?
C13 C12 C11 118.3(4) . . ?
C13 C12 H12 120.8 . . ?
C12 C13 C5 121.6(3) . . ?
C12 C13 C14 116.9(4) . . ?
C14 C13 C5 121.4(3) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 C13 119.3(4) . . ?
C15 C14 H14 120.3 . . ?
N4 C15 C14 124.9(4) . . ?
N4 C15 H15 117.5 . . ?
C14 C15 H15 117.5 . . ?
C17 C16 C3 121.8(3) . . ?
C21 C16 C3 120.4(3) . . ?
C21 C16 C17 117.8(3) . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.6(3) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 119.5 . . ?
C19 C18 C17 121.0(3) . . ?
C19 C18 H18 119.5 . . ?
C18 C19 N2 122.0(3) . . ?
C18 C19 C20 118.5(3) . . ?
C20 C19 N2 119.5(3) . . ?
C19 C20 H20 119.6 . . ?
C19 C20 C21 120.7(3) . . ?
C21 C20 H20 119.6 . . ?
C16 C21 H21 119.3 . . ?
C20 C21 C16 121.3(3) . . ?
C20 C21 H21 119.3 . . ?
C23 C22 N2 122.6(3) . . ?
C27 C22 N2 119.8(3) . . ?
C27 C22 C23 117.6(3) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 C22 120.5(3) . . ?
C24 C23 H23 119.8 . . ?
C23 C24 H24 119.6 . . ?
C25 C24 C23 120.8(4) . . ?
C25 C24 H24 119.6 . . ?
C24 C25 H25 120.3 . . ?
C26 C25 C24 119.4(4) . . ?
C26 C25 H25 120.3 . . ?
C25 C26 H26 119.8 . . ?
C25 C26 C27 120.4(4) . . ?
C27 C26 H26 119.8 . . ?
C22 C27 O1 121.7(3) . . ?
C26 C27 O1 117.0(3) . . ?
C26 C27 C22 121.3(3) . . ?
C29 C28 N2 123.7(3) . . ?
C29 C28 C33 116.7(3) . . ?
C33 C28 N2 119.6(3) . . ?
C28 C29 H29 119.4 . . ?
C28 C29 C30 121.3(4) . . ?
C30 C29 H29 119.4 . . ?
C29 C30 H30 119.8 . . ?
C31 C30 C29 120.5(4) . . ?
C31 C30 H30 119.8 . . ?
C30 C31 H31 120.5 . . ?
C30 C31 C32 118.9(4) . . ?
C32 C31 H31 120.5 . . ?
C31 C32 H32 120.0 . . ?
C33 C32 C31 120.0(4) . . ?
C33 C32 H32 120.0 . . ?
C28 C33 O1 121.6(3) . . ?
C32 C33 O1 115.7(3) . . ?
C32 C33 C28 122.7(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -0.3(4) . . . . ?
N1 C1 C8 C7 154.8(3) . . . . ?
N1 C1 C8 C9 -25.0(4) . . . . ?
N1 C5 C13 C12 31.6(5) . . . . ?
N1 C5 C13 C14 -146.3(3) . . . . ?
N2 C19 C20 C21 -178.9(3) . . . . ?
N2 C22 C23 C24 178.9(3) . . . . ?
N2 C22 C27 O1 1.4(5) . . . . ?
N2 C22 C27 C26 -178.5(3) . . . . ?
N2 C28 C29 C30 -179.6(4) . . . . ?
N2 C28 C33 O1 -1.9(5) . . . . ?
N2 C28 C33 C32 178.9(3) . . . . ?
N3 C6 C7 C8 -1.3(7) . . . . ?
N4 C11 C12 C13 2.4(7) . . . . ?
C1 N1 C5 C4 -1.0(4) . . . . ?
C1 N1 C5 C13 178.8(3) . . . . ?
C1 C2 C3 C4 -0.7(4) . . . . ?
C1 C2 C3 C16 179.2(3) . . . . ?
C1 C8 C9 C10 -179.0(3) . . . . ?
C2 C1 C8 C7 -26.3(5) . . . . ?
C2 C1 C8 C9 153.9(3) . . . . ?
C2 C3 C4 C5 0.8(4) . . . . ?
C2 C3 C16 C17 -150.0(3) . . . . ?
C2 C3 C16 C21 29.5(5) . . . . ?
C3 C4 C5 N1 0.0(5) . . . . ?
C3 C4 C5 C13 -179.8(3) . . . . ?
C3 C16 C17 C18 179.0(3) . . . . ?
C3 C16 C21 C20 -178.5(3) . . . . ?
C4 C3 C16 C17 29.8(5) . . . . ?
C4 C3 C16 C21 -150.6(3) . . . . ?
C4 C5 C13 C12 -148.6(3) . . . . ?
C4 C5 C13 C14 33.6(5) . . . . ?
C5 N1 C1 C2 1.2(4) . . . . ?
C5 N1 C1 C8 -180.0(3) . . . . ?
C5 C13 C14 C15 177.0(3) . . . . ?
C6 N3 C10 C9 3.2(7) . . . . ?
C6 C7 C8 C1 -178.8(3) . . . . ?
C6 C7 C8 C9 1.0(5) . . . . ?
C7 C8 C9 C10 1.2(5) . . . . ?
C8 C1 C2 C3 -179.1(3) . . . . ?
C8 C9 C10 N3 -3.5(6) . . . . ?
C10 N3 C6 C7 -0.8(7) . . . . ?
C11 N4 C15 C14 0.1(6) . . . . ?
C11 C12 C13 C5 -178.7(3) . . . . ?
C11 C12 C13 C14 -0.8(5) . . . . ?
C12 C13 C14 C15 -0.9(5) . . . . ?
C13 C14 C15 N4 1.4(6) . . . . ?
C15 N4 C11 C12 -2.0(6) . . . . ?
C16 C3 C4 C5 -179.0(3) . . . . ?
C16 C17 C18 C19 -0.6(5) . . . . ?
C17 C16 C21 C20 1.1(5) . . . . ?
C17 C18 C19 N2 179.3(3) . . . . ?
C17 C18 C19 C20 1.1(5) . . . . ?
C18 C19 C20 C21 -0.6(5) . . . . ?
C19 N2 C22 C23 8.6(5) . . . . ?
C19 N2 C22 C27 -172.8(3) . . . . ?
C19 N2 C28 C29 -7.0(5) . . . . ?
C19 N2 C28 C33 173.0(3) . . . . ?
C19 C20 C21 C16 -0.5(5) . . . . ?
C21 C16 C17 C18 -0.6(5) . . . . ?
C22 N2 C19 C18 -111.0(4) . . . . ?
C22 N2 C19 C20 67.2(4) . . . . ?
C22 N2 C28 C29 177.5(3) . . . . ?
C22 N2 C28 C33 -2.5(5) . . . . ?
C22 C23 C24 C25 -1.4(6) . . . . ?
C23 C22 C27 O1 -180.0(3) . . . . ?
C23 C22 C27 C26 0.2(5) . . . . ?
C23 C24 C25 C26 2.2(7) . . . . ?
C24 C25 C26 C27 -1.8(7) . . . . ?
C25 C26 C27 O1 -179.3(4) . . . . ?
C25 C26 C27 C22 0.6(6) . . . . ?
C27 O1 C33 C28 5.9(5) . . . . ?
C27 O1 C33 C32 -174.8(3) . . . . ?
C27 C22 C23 C24 0.2(6) . . . . ?
C28 N2 C19 C18 73.5(4) . . . . ?
C28 N2 C19 C20 -108.3(4) . . . . ?
C28 N2 C22 C23 -175.8(3) . . . . ?
C28 N2 C22 C27 2.8(5) . . . . ?
C28 C29 C30 C31 -0.5(7) . . . . ?
C29 C28 C33 O1 178.1(3) . . . . ?
C29 C28 C33 C32 -1.2(5) . . . . ?
C29 C30 C31 C32 1.2(8) . . . . ?
C30 C31 C32 C33 -1.9(7) . . . . ?
C31 C32 C33 O1 -177.3(4) . . . . ?
C31 C32 C33 C28 1.9(6) . . . . ?
C33 O1 C27 C22 -5.7(5) . . . . ?
C33 O1 C27 C26 174.2(3) . . . . ?
C33 C28 C29 C30 0.4(6) . . . . ?

_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_1
_database_code_depnum_ccdc_archive 'CCDC 1975856'
loop_
_audit_author_name
_audit_author_address
'Yi-Zhong Shi'
;Soochow University
China
;
_audit_update_record             
;
2020-01-07 deposited with the CCDC.	2020-08-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        
"10-(4-([3,2':6',3''-terpyridin]-4'-yl) phenyl)-10H-phenoxazine"
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H22 N4 O, C4 H8 O'
_chemical_formula_sum            'C37 H30 N4 O2'
_chemical_formula_weight         562.65

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

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

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

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

_cell_length_a                   8.7779(3)
_cell_length_b                   12.5445(4)
_cell_length_c                   14.1754(5)
_cell_angle_alpha                71.713(2)
_cell_angle_beta                 82.118(2)
_cell_angle_gamma                73.527(2)
_cell_volume                     1419.26(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8524
_cell_measurement_theta_min      2.9255
_cell_measurement_theta_max      27.1173

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light green'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   0.6942
_exptl_transmission_factor_max   0.7455
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.996
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SAINT V8.37A (Bruker AXS Inc., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Instrument Service vV6.2.1'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20407
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.925
_diffrn_reflns_theta_max         27.181
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6253
_reflns_number_gt                4646
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker Instrument Service vV6.2.1'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.1002P)²+1.8986P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6253
_refine_ls_number_parameters     388
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0990
_refine_ls_R_factor_gt           0.0732
_refine_ls_wR_factor_ref         0.2134
_refine_ls_wR_factor_gt          0.1943
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7317(2) -0.24393(17) 0.32779(16) 0.0415(5) Uani 1 1 d . . . . .
N1 N 0.4905(2) -0.05278(19) 0.23304(17) 0.0309(5) Uani 1 1 d . . . . .
N2 N -0.2042(3) 0.6469(2) -0.3942(2) 0.0466(6) Uani 1 1 d . U . . .
N3 N -0.5869(3) 0.7154(2) 0.04655(19) 0.0367(6) Uani 1 1 d . . . . .
N4 N -0.2178(2) 0.51620(16) -0.08581(15) 0.0205(4) Uani 1 1 d . . . . .
C4 C 0.6502(3) -0.0543(2) 0.20685(17) 0.0205(5) Uani 1 1 d . . . . .
C5 C 0.0202(3) 0.3636(2) -0.08583(18) 0.0205(5) Uani 1 1 d . . . . .
H5A H 0.103757 0.326713 -0.121795 0.025 Uiso 1 1 calc R U . . .
C6 C 0.0077(3) 0.32214(19) 0.01754(17) 0.0193(5) Uani 1 1 d . . . . .
C7 C -0.1214(3) 0.3793(2) 0.06739(18) 0.0217(5) Uani 1 1 d . . . . .
H7A H -0.134841 0.352772 0.136281 0.026 Uiso 1 1 calc R U . . .
C8 C -0.2307(3) 0.47665(19) 0.01340(17) 0.0197(5) Uani 1 1 d . . . . .
C9 C -0.0846(3) 0.5143(2) -0.24433(18) 0.0222(5) Uani 1 1 d . . . . .
C10 C -0.0944(3) 0.46139(19) -0.13498(17) 0.0205(5) Uani 1 1 d . . . . .
C11 C 0.4509(3) -0.1460(2) 0.30768(17) 0.0214(5) Uani 1 1 d . . . . .
C12 C 0.2167(3) 0.1340(2) 0.03319(18) 0.0215(5) Uani 1 1 d . . . . .
H12A H 0.195570 0.136095 -0.029964 0.026 Uiso 1 1 calc R U . . .
C13 C 0.1320(3) 0.22283(19) 0.07368(17) 0.0196(5) Uani 1 1 d . . . . .
C14 C -0.3651(3) 0.5454(2) 0.06368(18) 0.0214(5) Uani 1 1 d . . . . .
C15 C 0.3677(3) 0.0406(2) 0.17908(18) 0.0239(5) Uani 1 1 d . . . . .
C16 C 0.7687(3) -0.1509(2) 0.25406(18) 0.0234(5) Uani 1 1 d . . . . .
C17 C 0.5729(3) -0.2400(2) 0.35371(18) 0.0239(5) Uani 1 1 d . . . . .
C18 C 0.3327(3) 0.0424(2) 0.08645(19) 0.0240(5) Uani 1 1 d . . . . .
H18A H 0.386755 -0.017793 0.059747 0.029 Uiso 1 1 calc R U . . .
C19 C 0.6978(3) 0.0371(2) 0.13597(18) 0.0220(5) Uani 1 1 d . . . . .
H19A H 0.621586 0.102905 0.104562 0.026 Uiso 1 1 calc R U . . .
C20 C 0.2853(3) 0.1286(2) 0.22027(19) 0.0267(5) Uani 1 1 d . . . . .
H20A H 0.309425 0.127525 0.282475 0.032 Uiso 1 1 calc R U . . .
C22 C 0.1664(3) 0.2184(2) 0.16806(19) 0.0243(5) Uani 1 1 d . . . . .
H22A H 0.108919 0.276279 0.196507 0.029 Uiso 1 1 calc R U . . .
C23 C 0.0687(3) 0.5402(2) -0.40080(18) 0.0249(5) Uani 1 1 d . U . . .
H23A H 0.164251 0.521859 -0.436894 0.030 Uiso 1 1 calc R U . . .
C24 C 0.2955(3) -0.1499(2) 0.33780(19) 0.0263(5) Uani 1 1 d . . . . .
H24A H 0.212130 -0.088674 0.308093 0.032 Uiso 1 1 calc R U . . .
C25 C 0.9275(3) -0.1573(2) 0.22975(19) 0.0273(5) Uani 1 1 d . . . . .
H25A H 1.004135 -0.222581 0.261458 0.033 Uiso 1 1 calc R U . . .
C26 C 0.9731(3) -0.0663(2) 0.1580(2) 0.0308(6) Uani 1 1 d . . . . .
H26A H 1.080359 -0.070443 0.140869 0.037 Uiso 1 1 calc R U . . .
C27 C 0.8580(3) 0.0310(2) 0.11173(19) 0.0275(5) Uani 1 1 d . . . . .
H27A H 0.888398 0.092658 0.064107 0.033 Uiso 1 1 calc R U . . .
C28 C 0.5416(3) -0.3345(2) 0.42680(19) 0.0281(6) Uani 1 1 d . . . . .
H28A H 0.624722 -0.396307 0.455855 0.034 Uiso 1 1 calc R U . . .
C29 C -0.4663(3) 0.6461(2) 0.0078(2) 0.0300(6) Uani 1 1 d . . . . .
H29A H -0.448942 0.666690 -0.061041 0.036 Uiso 1 1 calc R U . . .
C30 C -0.2163(3) 0.5949(2) -0.2930(2) 0.0304(6) Uani 1 1 d . U . . .
H30A H -0.312061 0.613539 -0.257205 0.036 Uiso 1 1 calc R U . . .
C31 C -0.6100(3) 0.6845(2) 0.1451(2) 0.0324(6) Uani 1 1 d . . . . .
H31A H -0.692655 0.731800 0.173367 0.039 Uiso 1 1 calc R U . . .
C32 C 0.0548(3) 0.4920(2) -0.30254(19) 0.0285(5) Uani 1 1 d . U . . .
H32A H 0.144457 0.440225 -0.271061 0.034 Uiso 1 1 calc R U . . .
C33 C -0.3938(3) 0.5156(2) 0.1661(2) 0.0311(6) Uani 1 1 d . . . . .
H33A H -0.330071 0.448883 0.206633 0.037 Uiso 1 1 calc R U . . .
C34 C -0.0598(3) 0.6154(2) -0.4449(2) 0.0341(6) Uani 1 1 d . U . . .
H34A H -0.052340 0.648664 -0.513432 0.041 Uiso 1 1 calc R U . . .
C35 C 0.3853(4) -0.3369(2) 0.4569(2) 0.0348(6) Uani 1 1 d . . . . .
H35A H 0.362668 -0.399971 0.506820 0.042 Uiso 1 1 calc R U . . .
C36 C 0.2631(3) -0.2446(2) 0.4121(2) 0.0363(6) Uani 1 1 d . . . . .
H36A H 0.158104 -0.246051 0.432055 0.044 Uiso 1 1 calc R U . . .
C38 C -0.5186(3) 0.5864(2) 0.2076(2) 0.0338(6) Uani 1 1 d . . . . .
H38A H -0.539800 0.567795 0.276094 0.041 Uiso 1 1 calc R U . . .
C50 C 0.6363(5) 0.2114(4) 0.3246(3) 0.0652(11) Uani 1 1 d . . . . .
H50A H 0.611553 0.205890 0.261927 0.078 Uiso 1 1 calc R U . . .
H50B H 0.561865 0.279285 0.338024 0.078 Uiso 1 1 calc R U . . .
O2 O 0.7954(4) 0.2232(4) 0.3175(3) 0.1022(12) Uani 1 1 d . . . . .
C52 C 0.6195(6) 0.1052(5) 0.4060(4) 0.0853(14) Uani 1 1 d . . . . .
H52A H 0.558029 0.062827 0.386740 0.102 Uiso 1 1 calc R U . . .
H52B H 0.572104 0.123271 0.466894 0.102 Uiso 1 1 calc R U . . .
C53 C 0.8022(7) 0.0366(4) 0.4159(4) 0.0937(19) Uani 1 1 d . . . . .
H53A H 0.827869 0.004156 0.485320 0.112 Uiso 1 1 calc R U . . .
H53B H 0.827248 -0.025988 0.385391 0.112 Uiso 1 1 calc R U . . .
C54 C 0.8876(8) 0.1207(8) 0.3654(6) 0.140(3) Uani 1 1 d . . . . .
H54A H 0.945958 0.132058 0.413317 0.168 Uiso 1 1 calc R U . . .
H54B H 0.964626 0.090977 0.317839 0.168 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C16 1.384(3) . ?
O1 C17 1.383(3) . ?
N1 C4 1.397(3) . ?
N1 C11 1.400(3) . ?
N1 C15 1.438(3) . ?
N2 C30 1.380(4) . ?
N2 C34 1.387(4) . ?
N3 C31 1.330(4) . ?
N3 C29 1.341(3) . ?
N4 C8 1.337(3) . ?
N4 C10 1.343(3) . ?
C4 C19 1.390(3) . ?
C4 C16 1.401(3) . ?
C5 C6 1.393(3) . ?
C5 C10 1.399(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.391(3) . ?
C6 C13 1.490(3) . ?
C7 C8 1.396(3) . ?
C7 H7A 0.9300 . ?
C8 C14 1.490(3) . ?
C9 C32 1.389(3) . ?
C9 C30 1.398(3) . ?
C9 C10 1.484(3) . ?
C11 C24 1.382(3) . ?
C11 C17 1.399(3) . ?
C12 C18 1.390(3) . ?
C12 C13 1.392(3) . ?
C12 H12A 0.9300 . ?
C13 C22 1.392(3) . ?
C14 C33 1.386(4) . ?
C14 C29 1.394(3) . ?
C15 C18 1.381(4) . ?
C15 C20 1.384(4) . ?
C16 C25 1.375(3) . ?
C17 C28 1.374(3) . ?
C18 H18A 0.9300 . ?
C19 C27 1.388(3) . ?
C19 H19A 0.9300 . ?
C20 C22 1.389(3) . ?
C20 H20A 0.9300 . ?
C22 H22A 0.9300 . ?
C23 C34 1.332(4) . ?
C23 C32 1.337(3) . ?
C23 H23A 0.9300 . ?
C24 C36 1.388(4) . ?
C24 H24A 0.9300 . ?
C25 C26 1.385(4) . ?
C25 H25A 0.9300 . ?
C26 C27 1.386(4) . ?
C26 H26A 0.9300 . ?
C27 H27A 0.9300 . ?
C28 C35 1.386(4) . ?
C28 H28A 0.9300 . ?
C29 H29A 0.9300 . ?
C30 H30A 0.9300 . ?
C31 C38 1.376(4) . ?
C31 H31A 0.9300 . ?
C32 H32A 0.9300 . ?
C33 C38 1.391(4) . ?
C33 H33A 0.9300 . ?
C34 H34A 0.9300 . ?
C35 C36 1.384(4) . ?
C35 H35A 0.9300 . ?
C36 H36A 0.9300 . ?
C38 H38A 0.9300 . ?
C50 O2 1.433(6) . ?
C50 C52 1.492(7) . ?
C50 H50A 0.9700 . ?
C50 H50B 0.9700 . ?
O2 C54 1.335(7) . ?
C52 C53 1.593(7) . ?
C52 H52A 0.9700 . ?
C52 H52B 0.9700 . ?
C53 C54 1.420(9) . ?
C53 H53A 0.9700 . ?
C53 H53B 0.9700 . ?
C54 H54A 0.9700 . ?
C54 H54B 0.9700 . ?

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
C16 O1 C17 118.09(19) . . ?
C4 N1 C11 119.72(19) . . ?
C4 N1 C15 119.95(19) . . ?
C11 N1 C15 120.20(19) . . ?
C30 N2 C34 118.1(2) . . ?
C31 N3 C29 116.9(2) . . ?
C8 N4 C10 118.90(19) . . ?
C19 C4 N1 122.7(2) . . ?
C19 C4 C16 118.0(2) . . ?
N1 C4 C16 119.3(2) . . ?
C6 C5 C10 119.2(2) . . ?
C6 C5 H5A 120.4 . . ?
C10 C5 H5A 120.4 . . ?
C5 C6 C7 117.9(2) . . ?
C5 C6 C13 121.3(2) . . ?
C7 C6 C13 120.8(2) . . ?
C6 C7 C8 119.6(2) . . ?
C6 C7 H7A 120.2 . . ?
C8 C7 H7A 120.2 . . ?
N4 C8 C7 122.1(2) . . ?
N4 C8 C14 116.14(19) . . ?
C7 C8 C14 121.7(2) . . ?
C32 C9 C30 116.7(2) . . ?
C32 C9 C10 122.8(2) . . ?
C30 C9 C10 120.4(2) . . ?
N4 C10 C5 122.2(2) . . ?
N4 C10 C9 115.4(2) . . ?
C5 C10 C9 122.4(2) . . ?
C24 C11 C17 118.1(2) . . ?
C24 C11 N1 122.8(2) . . ?
C17 C11 N1 119.1(2) . . ?
C18 C12 C13 120.5(2) . . ?
C18 C12 H12A 119.8 . . ?
C13 C12 H12A 119.8 . . ?
C22 C13 C12 118.8(2) . . ?
C22 C13 C6 119.9(2) . . ?
C12 C13 C6 121.3(2) . . ?
C33 C14 C29 116.9(2) . . ?
C33 C14 C8 122.9(2) . . ?
C29 C14 C8 120.1(2) . . ?
C18 C15 C20 120.4(2) . . ?
C18 C15 N1 119.9(2) . . ?
C20 C15 N1 119.7(2) . . ?
C25 C16 O1 116.8(2) . . ?
C25 C16 C4 121.5(2) . . ?
O1 C16 C4 121.7(2) . . ?
C28 C17 O1 116.2(2) . . ?
C28 C17 C11 121.8(2) . . ?
O1 C17 C11 122.1(2) . . ?
C15 C18 C12 120.0(2) . . ?
C15 C18 H18A 120.0 . . ?
C12 C18 H18A 120.0 . . ?
C27 C19 C4 120.5(2) . . ?
C27 C19 H19A 119.7 . . ?
C4 C19 H19A 119.7 . . ?
C15 C20 C22 119.5(2) . . ?
C15 C20 H20A 120.2 . . ?
C22 C20 H20A 120.2 . . ?
C20 C22 C13 120.9(2) . . ?
C20 C22 H22A 119.6 . . ?
C13 C22 H22A 119.6 . . ?
C34 C23 C32 117.3(2) . . ?
C34 C23 H23A 121.3 . . ?
C32 C23 H23A 121.3 . . ?
C11 C24 C36 120.4(2) . . ?
C11 C24 H24A 119.8 . . ?
C36 C24 H24A 119.8 . . ?
C16 C25 C26 119.9(2) . . ?
C16 C25 H25A 120.1 . . ?
C26 C25 H25A 120.1 . . ?
C25 C26 C27 119.6(2) . . ?
C25 C26 H26A 120.2 . . ?
C27 C26 H26A 120.2 . . ?
C26 C27 C19 120.5(2) . . ?
C26 C27 H27A 119.8 . . ?
C19 C27 H27A 119.8 . . ?
C17 C28 C35 119.6(2) . . ?
C17 C28 H28A 120.2 . . ?
C35 C28 H28A 120.2 . . ?
N3 C29 C14 124.4(2) . . ?
N3 C29 H29A 117.8 . . ?
C14 C29 H29A 117.8 . . ?
N2 C30 C9 120.0(2) . . ?
N2 C30 H30A 120.0 . . ?
C9 C30 H30A 120.0 . . ?
N3 C31 C38 123.8(2) . . ?
N3 C31 H31A 118.1 . . ?
C38 C31 H31A 118.1 . . ?
C23 C32 C9 124.4(2) . . ?
C23 C32 H32A 117.8 . . ?
C9 C32 H32A 117.8 . . ?
C14 C33 C38 119.5(2) . . ?
C14 C33 H33A 120.3 . . ?
C38 C33 H33A 120.3 . . ?
C23 C34 N2 123.5(2) . . ?
C23 C34 H34A 118.3 . . ?
N2 C34 H34A 118.3 . . ?
C36 C35 C28 119.4(2) . . ?
C36 C35 H35A 120.3 . . ?
C28 C35 H35A 120.3 . . ?
C35 C36 C24 120.8(3) . . ?
C35 C36 H36A 119.6 . . ?
C24 C36 H36A 119.6 . . ?
C31 C38 C33 118.5(3) . . ?
C31 C38 H38A 120.7 . . ?
C33 C38 H38A 120.7 . . ?
O2 C50 C52 110.1(4) . . ?
O2 C50 H50A 109.6 . . ?
C52 C50 H50A 109.6 . . ?
O2 C50 H50B 109.6 . . ?
C52 C50 H50B 109.6 . . ?
H50A C50 H50B 108.2 . . ?
C54 O2 C50 107.8(5) . . ?
C50 C52 C53 99.3(4) . . ?
C50 C52 H52A 111.9 . . ?
C53 C52 H52A 111.9 . . ?
C50 C52 H52B 111.9 . . ?
C53 C52 H52B 111.9 . . ?
H52A C52 H52B 109.6 . . ?
C54 C53 C52 105.0(4) . . ?
C54 C53 H53A 110.7 . . ?
C52 C53 H53A 110.7 . . ?
C54 C53 H53B 110.7 . . ?
C52 C53 H53B 110.7 . . ?
H53A C53 H53B 108.8 . . ?
O2 C54 C53 113.8(6) . . ?
O2 C54 H54A 108.8 . . ?
C53 C54 H54A 108.8 . . ?
O2 C54 H54B 108.8 . . ?
C53 C54 H54B 108.8 . . ?
H54A C54 H54B 107.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 N1 C4 C19 -177.6(2) . . . . ?
C15 N1 C4 C19 6.4(4) . . . . ?
C11 N1 C4 C16 1.7(4) . . . . ?
C15 N1 C4 C16 -174.4(2) . . . . ?
C10 C5 C6 C7 1.3(3) . . . . ?
C10 C5 C6 C13 -176.2(2) . . . . ?
C5 C6 C7 C8 -1.6(3) . . . . ?
C13 C6 C7 C8 175.9(2) . . . . ?
C10 N4 C8 C7 -0.9(3) . . . . ?
C10 N4 C8 C14 176.7(2) . . . . ?
C6 C7 C8 N4 1.4(3) . . . . ?
C6 C7 C8 C14 -176.0(2) . . . . ?
C8 N4 C10 C5 0.6(3) . . . . ?
C8 N4 C10 C9 -177.1(2) . . . . ?
C6 C5 C10 N4 -0.8(3) . . . . ?
C6 C5 C10 C9 176.7(2) . . . . ?
C32 C9 C10 N4 160.4(2) . . . . ?
C30 C9 C10 N4 -16.2(3) . . . . ?
C32 C9 C10 C5 -17.3(4) . . . . ?
C30 C9 C10 C5 166.1(2) . . . . ?
C4 N1 C11 C24 179.6(2) . . . . ?
C15 N1 C11 C24 -4.4(4) . . . . ?
C4 N1 C11 C17 -0.9(4) . . . . ?
C15 N1 C11 C17 175.1(2) . . . . ?
C18 C12 C13 C22 0.4(3) . . . . ?
C18 C12 C13 C6 179.7(2) . . . . ?
C5 C6 C13 C22 147.3(2) . . . . ?
C7 C6 C13 C22 -30.2(3) . . . . ?
C5 C6 C13 C12 -32.0(3) . . . . ?
C7 C6 C13 C12 150.6(2) . . . . ?
N4 C8 C14 C33 -179.8(2) . . . . ?
C7 C8 C14 C33 -2.2(4) . . . . ?
N4 C8 C14 C29 -1.5(3) . . . . ?
C7 C8 C14 C29 176.1(2) . . . . ?
C4 N1 C15 C18 77.4(3) . . . . ?
C11 N1 C15 C18 -98.6(3) . . . . ?
C4 N1 C15 C20 -102.5(3) . . . . ?
C11 N1 C15 C20 81.5(3) . . . . ?
C17 O1 C16 C25 -179.9(2) . . . . ?
C17 O1 C16 C4 0.5(4) . . . . ?
C19 C4 C16 C25 -1.7(4) . . . . ?
N1 C4 C16 C25 179.0(2) . . . . ?
C19 C4 C16 O1 177.8(2) . . . . ?
N1 C4 C16 O1 -1.5(4) . . . . ?
C16 O1 C17 C28 179.6(2) . . . . ?
C16 O1 C17 C11 0.2(4) . . . . ?
C24 C11 C17 C28 0.1(4) . . . . ?
N1 C11 C17 C28 -179.4(2) . . . . ?
C24 C11 C17 O1 179.5(2) . . . . ?
N1 C11 C17 O1 0.0(4) . . . . ?
C20 C15 C18 C12 1.4(4) . . . . ?
N1 C15 C18 C12 -178.4(2) . . . . ?
C13 C12 C18 C15 -1.8(3) . . . . ?
N1 C4 C19 C27 -179.3(2) . . . . ?
C16 C4 C19 C27 1.4(4) . . . . ?
C18 C15 C20 C22 0.4(4) . . . . ?
N1 C15 C20 C22 -179.7(2) . . . . ?
C15 C20 C22 C13 -1.8(4) . . . . ?
C12 C13 C22 C20 1.4(4) . . . . ?
C6 C13 C22 C20 -177.9(2) . . . . ?
C17 C11 C24 C36 0.4(4) . . . . ?
N1 C11 C24 C36 179.9(3) . . . . ?
O1 C16 C25 C26 -178.8(2) . . . . ?
C4 C16 C25 C26 0.8(4) . . . . ?
C16 C25 C26 C27 0.5(4) . . . . ?
C25 C26 C27 C19 -0.8(4) . . . . ?
C4 C19 C27 C26 -0.1(4) . . . . ?
O1 C17 C28 C35 179.9(2) . . . . ?
C11 C17 C28 C35 -0.6(4) . . . . ?
C31 N3 C29 C14 -0.1(4) . . . . ?
C33 C14 C29 N3 0.6(4) . . . . ?
C8 C14 C29 N3 -177.8(2) . . . . ?
C34 N2 C30 C9 0.9(4) . . . . ?
C32 C9 C30 N2 0.8(4) . . . . ?
C10 C9 C30 N2 177.6(2) . . . . ?
C29 N3 C31 C38 -0.5(4) . . . . ?
C34 C23 C32 C9 0.9(4) . . . . ?
C30 C9 C32 C23 -1.7(4) . . . . ?
C10 C9 C32 C23 -178.4(2) . . . . ?
C29 C14 C33 C38 -0.4(4) . . . . ?
C8 C14 C33 C38 177.9(2) . . . . ?
C32 C23 C34 N2 1.0(4) . . . . ?
C30 N2 C34 C23 -1.8(5) . . . . ?
C17 C28 C35 C36 0.7(4) . . . . ?
C28 C35 C36 C24 -0.2(4) . . . . ?
C11 C24 C36 C35 -0.4(4) . . . . ?
N3 C31 C38 C33 0.6(4) . . . . ?
C14 C33 C38 C31 -0.1(4) . . . . ?
C52 C50 O2 C54 17.3(6) . . . . ?
O2 C50 C52 C53 -19.8(5) . . . . ?
C50 C52 C53 C54 15.7(6) . . . . ?
C50 O2 C54 C53 -5.9(8) . . . . ?
C52 C53 C54 O2 -6.9(8) . . . . ?

_refine_diff_density_max         0.875
_refine_diff_density_min         -0.683
_refine_diff_density_rms         0.071

