# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_t_b
_database_code_depnum_ccdc_archive 'CCDC 1890881'
loop_
_audit_author_name
_audit_author_address
'Jie Sun'
;Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2019-01-15 deposited with the CCDC.	2019-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
(S)-2-hexyl-7-(2-phenylpropyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H28 N2 O4'
_chemical_formula_sum            'C29 H28 N2 O4'
_chemical_formula_weight         468.53

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

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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'

_cell_length_a                   4.7639(13)
_cell_length_b                   8.744(2)
_cell_length_c                   14.310(7)
_cell_angle_alpha                90.45(5)
_cell_angle_beta                 93.46(3)
_cell_angle_gamma                96.76(3)
_cell_volume                     590.8(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9538
_cell_measurement_theta_min      3.09
_cell_measurement_theta_max      68.50

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_F_000             248
_exptl_transmission_factor_min   0.4922
_exptl_transmission_factor_max   0.7531
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.709
_shelx_estimated_absorpt_T_min   0.848
_shelx_estimated_absorpt_T_max   0.871
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10980
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.094
_diffrn_reflns_theta_max         68.378
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.963
_reflns_number_total             3888
_reflns_number_gt                3538
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         1.000
_reflns_Friedel_fraction_max     0.961
_reflns_Friedel_fraction_full    0.963

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0770P)²+0.4288P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.1(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3888
_refine_ls_number_parameters     319
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0704
_refine_ls_wR_factor_ref         0.1886
_refine_ls_wR_factor_gt          0.1829
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.104
_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 1.0492(10) 0.2748(5) 0.7523(3) 0.0564(13) Uani 1 1 d . . . . .
C1 C 0.8393(13) 0.2572(7) 0.6979(5) 0.0442(16) Uani 1 1 d . . . . .
N1 N 0.6743(11) 0.1174(6) 0.6879(4) 0.0443(13) Uani 1 1 d . . . . .
O2 O 0.2979(10) -0.0392(5) 0.6252(3) 0.0535(12) Uani 1 1 d . . . . .
C2 C 0.7593(13) 0.3865(7) 0.6378(4) 0.0402(15) Uani 1 1 d . . . . .
N2 N 0.3150(10) 0.7165(6) 0.3925(4) 0.0394(12) Uani 1 1 d . . . . .
C3 C 0.5323(13) 0.3577(6) 0.5707(4) 0.0365(14) Uani 1 1 d . . . . .
O3 O 0.6809(9) 0.8769(5) 0.4602(3) 0.0469(11) Uani 1 1 d . . . . .
C5 C 0.4362(14) 0.0844(7) 0.6263(4) 0.0422(15) Uani 1 1 d . . . . .
O4 O -0.0608(9) 0.5574(5) 0.3286(3) 0.0532(12) Uani 1 1 d . . . . .
C4 C 0.3716(11) 0.2101(6) 0.5622(4) 0.0363(14) Uani 1 1 d . . . . .
C7 C 0.8411(13) 0.6511(6) 0.5871(4) 0.0411(15) Uani 1 1 d . . . . .
H7 H 0.944617 0.750732 0.593794 0.049 Uiso 1 1 calc R U . . .
C6 C 0.9122(12) 0.5305(7) 0.6450(4) 0.0400(15) Uani 1 1 d . . . . .
H6 H 1.068405 0.548624 0.689750 0.048 Uiso 1 1 calc R U . . .
C8 C 0.6191(13) 0.6229(6) 0.5205(4) 0.0398(15) Uani 1 1 d . . . . .
C9 C 0.4615(12) 0.4777(6) 0.5105(4) 0.0351(14) Uani 1 1 d . . . . .
C10 C 0.2291(12) 0.4480(7) 0.4436(4) 0.0376(14) Uani 1 1 d . . . . .
C11 C 0.0799(13) 0.3037(7) 0.4355(4) 0.0456(16) Uani 1 1 d . . . . .
H11 H -0.070215 0.283542 0.388662 0.055 Uiso 1 1 calc R U . . .
C12 C 0.1471(13) 0.1857(7) 0.4958(4) 0.0426(15) Uani 1 1 d . . . . .
H12 H 0.036893 0.087736 0.490971 0.051 Uiso 1 1 calc R U . . .
C13 C 0.5435(13) 0.7497(7) 0.4570(4) 0.0385(14) Uani 1 1 d . . . . .
C14 C 0.1438(13) 0.5738(7) 0.3842(4) 0.0433(16) Uani 1 1 d . . . . .
C15 C 0.2347(14) 0.8454(7) 0.3336(5) 0.0453(16) Uani 1 1 d . . . . .
H15A H 0.250258 0.940238 0.372750 0.054 Uiso 1 1 calc R U . . .
H15B H 0.034409 0.821770 0.310052 0.054 Uiso 1 1 calc R U . . .
C16 C 0.4191(14) 0.8753(7) 0.2503(4) 0.0455(15) Uani 1 1 d . . . . .
H16 H 0.619603 0.896714 0.276332 0.055 Uiso 1 1 calc R U . . .
C17 C 0.4057(19) 0.7378(8) 0.1847(5) 0.0687(19) Uani 1 1 d . . . . .
H17A H 0.208149 0.705352 0.163376 0.103 Uiso 1 1 calc R U . . .
H17B H 0.483672 0.653010 0.217737 0.103 Uiso 1 1 calc R U . . .
H17C H 0.516396 0.766008 0.130631 0.103 Uiso 1 1 calc R U . . .
C18 C 0.3445(13) 1.0222(7) 0.2030(4) 0.0429(14) Uani 1 1 d . . . . .
C19 C 0.146(2) 1.0217(9) 0.1316(8) 0.112(4) Uani 1 1 d . . . . .
H19 H 0.050088 0.926962 0.107297 0.135 Uiso 1 1 calc R U . . .
C20 C 0.081(3) 1.1623(12) 0.0933(10) 0.142(6) Uani 1 1 d . . . . .
H20 H -0.062273 1.161465 0.044188 0.170 Uiso 1 1 calc R U . . .
C21 C 0.221(2) 1.2998(9) 0.1254(7) 0.079(3) Uani 1 1 d . . . . .
H21 H 0.179288 1.394412 0.098896 0.095 Uiso 1 1 calc R U . . .
C22 C 0.416(3) 1.2967(9) 0.1942(8) 0.110(4) Uani 1 1 d . . . . .
H22 H 0.517611 1.390925 0.216915 0.132 Uiso 1 1 calc R U . . .
C23 C 0.478(3) 1.1597(10) 0.2347(9) 0.114(5) Uani 1 1 d . . . . .
H23 H 0.615741 1.162677 0.285587 0.136 Uiso 1 1 calc R U . . .
C24 C 0.7410(14) -0.0089(7) 0.7515(5) 0.0498(17) Uani 1 1 d . . . . .
H24A H 0.948794 -0.001852 0.764125 0.060 Uiso 1 1 calc R U . . .
H24B H 0.677476 -0.109153 0.719801 0.060 Uiso 1 1 calc R U . . .
C25 C 0.6032(18) -0.0039(8) 0.8427(5) 0.0563(18) Uani 1 1 d . . . . .
H25A H 0.395181 -0.012887 0.830258 0.068 Uiso 1 1 calc R U . . .
H25B H 0.664169 0.096965 0.874026 0.068 Uiso 1 1 calc R U . . .
C26 C 0.6765(18) -0.1317(9) 0.9079(5) 0.067(2) Uani 1 1 d . . . . .
H26A H 0.884035 -0.118454 0.922102 0.081 Uiso 1 1 calc R U . . .
H26B H 0.586268 -0.118811 0.967540 0.081 Uiso 1 1 calc R U . . .
C27 C 0.591(3) -0.2923(9) 0.8726(6) 0.089(3) Uani 1 1 d . . . . .
H27A H 0.690469 -0.309432 0.815376 0.107 Uiso 1 1 calc R U . . .
H27B H 0.384886 -0.306199 0.855666 0.107 Uiso 1 1 calc R U . . .
C28 C 0.662(4) -0.4146(11) 0.9475(8) 0.154(7) Uani 1 1 d . . . . .
H28A H 0.856248 -0.383745 0.974676 0.184 Uiso 1 1 calc R U . . .
H28B H 0.531689 -0.409647 0.998555 0.184 Uiso 1 1 calc R U . . .
C29 C 0.645(4) -0.5627(14) 0.9180(9) 0.144(6) Uani 1 1 d . . . . .
H29A H 0.449294 -0.598745 0.895963 0.217 Uiso 1 1 calc R U . . .
H29B H 0.703107 -0.626571 0.969960 0.217 Uiso 1 1 calc R U . . .
H29C H 0.769957 -0.570192 0.866660 0.217 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 C1 1.224(8) . ?
C1 N1 1.375(8) . ?
C1 C2 1.496(8) . ?
N1 C5 1.394(9) . ?
N1 C24 1.487(9) . ?
O2 C5 1.198(8) . ?
C2 C6 1.379(8) . ?
C2 C3 1.401(8) . ?
N2 C13 1.386(8) . ?
N2 C14 1.408(8) . ?
N2 C15 1.486(8) . ?
C3 C9 1.420(6) . ?
C3 C4 1.422(8) . ?
O3 C13 1.221(7) . ?
C5 C4 1.486(8) . ?
O4 C14 1.214(7) . ?
C4 C12 1.383(8) . ?
C7 C8 1.379(9) . ?
C7 C6 1.406(8) . ?
C7 H7 0.9500 . ?
C6 H6 0.9500 . ?
C8 C9 1.398(8) . ?
C8 C13 1.502(9) . ?
C9 C10 1.418(8) . ?
C10 C11 1.374(9) . ?
C10 C14 1.475(9) . ?
C11 C12 1.404(9) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C15 C16 1.529(9) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.511(9) . ?
C16 C18 1.526(8) . ?
C16 H16 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.349(9) . ?
C18 C23 1.353(10) . ?
C19 C20 1.410(11) . ?
C19 H19 0.9500 . ?
C20 C21 1.366(13) . ?
C20 H20 0.9500 . ?
C21 C22 1.314(12) . ?
C21 H21 0.9500 . ?
C22 C23 1.389(12) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C25 1.498(10) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.521(9) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.491(12) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.569(12) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.351(15) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N1 121.3(6) . . ?
O1 C1 C2 120.8(6) . . ?
N1 C1 C2 117.9(5) . . ?
C1 N1 C5 125.7(5) . . ?
C1 N1 C24 118.3(6) . . ?
C5 N1 C24 115.9(5) . . ?
C6 C2 C3 119.9(6) . . ?
C6 C2 C1 121.1(6) . . ?
C3 C2 C1 118.9(5) . . ?
C13 N2 C14 124.7(5) . . ?
C13 N2 C15 116.8(5) . . ?
C14 N2 C15 118.3(5) . . ?
C2 C3 C9 119.6(4) . . ?
C2 C3 C4 120.8(5) . . ?
C9 C3 C4 119.6(4) . . ?
O2 C5 N1 121.1(6) . . ?
O2 C5 C4 123.0(6) . . ?
N1 C5 C4 115.9(5) . . ?
C12 C4 C3 119.5(5) . . ?
C12 C4 C5 120.0(5) . . ?
C3 C4 C5 120.5(5) . . ?
C8 C7 C6 119.1(5) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C2 C6 C7 121.2(6) . . ?
C2 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C7 C8 C9 121.3(5) . . ?
C7 C8 C13 119.8(5) . . ?
C9 C8 C13 118.9(5) . . ?
C8 C9 C10 121.8(5) . . ?
C8 C9 C3 119.0(4) . . ?
C10 C9 C3 119.1(4) . . ?
C11 C10 C9 120.2(6) . . ?
C11 C10 C14 120.1(5) . . ?
C9 C10 C14 119.7(5) . . ?
C10 C11 C12 120.7(6) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C4 C12 C11 120.9(6) . . ?
C4 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
O3 C13 N2 120.7(6) . . ?
O3 C13 C8 121.7(5) . . ?
N2 C13 C8 117.6(5) . . ?
O4 C14 N2 120.1(6) . . ?
O4 C14 C10 122.8(6) . . ?
N2 C14 C10 117.1(5) . . ?
N2 C15 C16 113.0(5) . . ?
N2 C15 H15A 109.0 . . ?
C16 C15 H15A 109.0 . . ?
N2 C15 H15B 109.0 . . ?
C16 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C17 C16 C18 114.3(5) . . ?
C17 C16 C15 113.2(6) . . ?
C18 C16 C15 108.3(4) . . ?
C17 C16 H16 106.9 . . ?
C18 C16 H16 106.9 . . ?
C15 C16 H16 106.9 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C23 118.1(6) . . ?
C19 C18 C16 122.8(6) . . ?
C23 C18 C16 119.1(6) . . ?
C18 C19 C20 119.7(8) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C21 C20 C19 121.3(8) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C22 C21 C20 117.7(8) . . ?
C22 C21 H21 121.2 . . ?
C20 C21 H21 121.2 . . ?
C21 C22 C23 122.0(8) . . ?
C21 C22 H22 119.0 . . ?
C23 C22 H22 119.0 . . ?
C18 C23 C22 121.2(8) . . ?
C18 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
N1 C24 C25 112.8(5) . . ?
N1 C24 H24A 109.0 . . ?
C25 C24 H24A 109.0 . . ?
N1 C24 H24B 109.0 . . ?
C25 C24 H24B 109.0 . . ?
H24A C24 H24B 107.8 . . ?
C24 C25 C26 112.5(6) . . ?
C24 C25 H25A 109.1 . . ?
C26 C25 H25A 109.1 . . ?
C24 C25 H25B 109.1 . . ?
C26 C25 H25B 109.1 . . ?
H25A C25 H25B 107.8 . . ?
C27 C26 C25 116.2(7) . . ?
C27 C26 H26A 108.2 . . ?
C25 C26 H26A 108.2 . . ?
C27 C26 H26B 108.2 . . ?
C25 C26 H26B 108.2 . . ?
H26A C26 H26B 107.4 . . ?
C26 C27 C28 111.9(8) . . ?
C26 C27 H27A 109.2 . . ?
C28 C27 H27A 109.2 . . ?
C26 C27 H27B 109.2 . . ?
C28 C27 H27B 109.2 . . ?
H27A C27 H27B 107.9 . . ?
C29 C28 C27 117.2(10) . . ?
C29 C28 H28A 108.0 . . ?
C27 C28 H28A 108.0 . . ?
C29 C28 H28B 108.0 . . ?
C27 C28 H28B 108.0 . . ?
H28A C28 H28B 107.2 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 N1 C5 -178.3(6) . . . . ?
C2 C1 N1 C5 0.0(9) . . . . ?
O1 C1 N1 C24 5.6(10) . . . . ?
C2 C1 N1 C24 -176.1(6) . . . . ?
O1 C1 C2 C6 -2.7(10) . . . . ?
N1 C1 C2 C6 179.0(6) . . . . ?
O1 C1 C2 C3 174.4(6) . . . . ?
N1 C1 C2 C3 -3.8(9) . . . . ?
C6 C2 C3 C9 -0.1(8) . . . . ?
C1 C2 C3 C9 -177.4(5) . . . . ?
C6 C2 C3 C4 -179.9(6) . . . . ?
C1 C2 C3 C4 2.9(9) . . . . ?
C1 N1 C5 O2 -176.9(6) . . . . ?
C24 N1 C5 O2 -0.6(10) . . . . ?
C1 N1 C5 C4 4.4(9) . . . . ?
C24 N1 C5 C4 -179.4(6) . . . . ?
C2 C3 C4 C12 179.4(6) . . . . ?
C9 C3 C4 C12 -0.4(8) . . . . ?
C2 C3 C4 C5 1.7(8) . . . . ?
C9 C3 C4 C5 -178.0(4) . . . . ?
O2 C5 C4 C12 -1.6(10) . . . . ?
N1 C5 C4 C12 177.1(6) . . . . ?
O2 C5 C4 C3 176.0(6) . . . . ?
N1 C5 C4 C3 -5.2(8) . . . . ?
C3 C2 C6 C7 1.4(10) . . . . ?
C1 C2 C6 C7 178.5(6) . . . . ?
C8 C7 C6 C2 -1.8(10) . . . . ?
C6 C7 C8 C9 1.0(10) . . . . ?
C6 C7 C8 C13 -179.0(5) . . . . ?
C7 C8 C9 C10 178.7(6) . . . . ?
C13 C8 C9 C10 -1.4(8) . . . . ?
C7 C8 C9 C3 0.2(8) . . . . ?
C13 C8 C9 C3 -179.9(5) . . . . ?
C2 C3 C9 C8 -0.6(7) . . . . ?
C4 C3 C9 C8 179.1(6) . . . . ?
C2 C3 C9 C10 -179.2(6) . . . . ?
C4 C3 C9 C10 0.6(6) . . . . ?
C8 C9 C10 C11 179.7(6) . . . . ?
C3 C9 C10 C11 -1.8(8) . . . . ?
C8 C9 C10 C14 -1.7(8) . . . . ?
C3 C9 C10 C14 176.8(5) . . . . ?
C9 C10 C11 C12 2.8(9) . . . . ?
C14 C10 C11 C12 -175.8(6) . . . . ?
C3 C4 C12 C11 1.3(9) . . . . ?
C5 C4 C12 C11 179.0(5) . . . . ?
C10 C11 C12 C4 -2.6(10) . . . . ?
C14 N2 C13 O3 -179.6(6) . . . . ?
C15 N2 C13 O3 -4.5(9) . . . . ?
C14 N2 C13 C8 2.0(9) . . . . ?
C15 N2 C13 C8 177.1(5) . . . . ?
C7 C8 C13 O3 2.9(9) . . . . ?
C9 C8 C13 O3 -177.1(6) . . . . ?
C7 C8 C13 N2 -178.7(6) . . . . ?
C9 C8 C13 N2 1.4(8) . . . . ?
C13 N2 C14 O4 176.4(6) . . . . ?
C15 N2 C14 O4 1.3(10) . . . . ?
C13 N2 C14 C10 -5.0(9) . . . . ?
C15 N2 C14 C10 180.0(5) . . . . ?
C11 C10 C14 O4 2.0(10) . . . . ?
C9 C10 C14 O4 -176.6(6) . . . . ?
C11 C10 C14 N2 -176.7(6) . . . . ?
C9 C10 C14 N2 4.8(8) . . . . ?
C13 N2 C15 C16 81.0(7) . . . . ?
C14 N2 C15 C16 -103.6(7) . . . . ?
N2 C15 C16 C17 59.8(7) . . . . ?
N2 C15 C16 C18 -172.5(6) . . . . ?
C17 C16 C18 C19 35.3(11) . . . . ?
C15 C16 C18 C19 -91.8(10) . . . . ?
C17 C16 C18 C23 -146.2(9) . . . . ?
C15 C16 C18 C23 86.7(10) . . . . ?
C23 C18 C19 C20 -0.7(17) . . . . ?
C16 C18 C19 C20 177.9(11) . . . . ?
C18 C19 C20 C21 2(2) . . . . ?
C19 C20 C21 C22 -1(2) . . . . ?
C20 C21 C22 C23 -1(2) . . . . ?
C19 C18 C23 C22 -1.1(18) . . . . ?
C16 C18 C23 C22 -179.7(11) . . . . ?
C21 C22 C23 C18 2(2) . . . . ?
C1 N1 C24 C25 85.8(8) . . . . ?
C5 N1 C24 C25 -90.8(7) . . . . ?
N1 C24 C25 C26 -179.0(6) . . . . ?
C24 C25 C26 C27 -60.6(10) . . . . ?
C25 C26 C27 C28 -176.8(9) . . . . ?
C26 C27 C28 C29 -167.6(15) . . . . ?

_refine_diff_density_max         0.205
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_d8v18583
_database_code_depnum_ccdc_archive 'CCDC 1890882'
loop_
_audit_author_name
_audit_author_address
'Jie Sun'
;Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2019-01-15 deposited with the CCDC.	2019-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
(R)-2-hexyl-7-(2-phenylpropyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H28 N2 O4'
_chemical_formula_weight         468.53

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

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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'

_cell_length_a                   4.8296(2)
_cell_length_b                   8.7435(3)
_cell_length_c                   14.4477(5)
_cell_angle_alpha                89.9140(10)
_cell_angle_beta                 86.0960(10)
_cell_angle_gamma                82.5490(10)
_cell_volume                     603.52(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9943
_cell_measurement_theta_min      10.203
_cell_measurement_theta_max      140.099

_exptl_crystal_description       prismatic
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_F_000             248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.694
_shelx_estimated_absorpt_T_min   0.879
_shelx_estimated_absorpt_T_max   0.934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5986
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17553
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         5.102
_diffrn_reflns_theta_max         66.493
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.941
_reflns_number_total             4116
_reflns_number_gt                3943
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.967
_reflns_Friedel_fraction_max     0.948
_reflns_Friedel_fraction_full    0.926

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1019P)²+0.0524P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1856 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.05(8)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4116
_refine_ls_number_parameters     332
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_ref         0.1564
_refine_ls_wR_factor_gt          0.1536
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.9869(6) 0.5789(3) 0.43008(19) 0.0543(7) Uani 1 1 d . . . . .
N2 N 0.6287(6) -0.0180(3) 0.7255(2) 0.0592(7) Uani 1 1 d . . . . .
O1 O 1.3614(5) 0.4188(3) 0.3686(2) 0.0768(8) Uani 1 1 d . . . . .
O2 O 0.6245(6) 0.7401(3) 0.49665(19) 0.0703(7) Uani 1 1 d . . . . .
O3 O 1.0006(6) -0.1768(3) 0.6626(2) 0.0764(8) Uani 1 1 d . . . . .
O4 O 0.2557(6) 0.1403(3) 0.7881(2) 0.0805(8) Uani 1 1 d . . . . .
C1 C 1.1568(7) 0.4364(4) 0.4218(2) 0.0564(8) Uani 1 1 d . . . . .
C2 C 0.7572(6) 0.6132(3) 0.4938(2) 0.0514(8) Uani 1 1 d . . . . .
C3 C 0.6861(6) 0.4875(3) 0.5572(2) 0.0492(8) Uani 1 1 d . . . . .
C4 C 0.8443(6) 0.3407(3) 0.5487(2) 0.0458(7) Uani 1 1 d . . . . .
C5 C 1.0733(6) 0.3098(4) 0.4821(2) 0.0519(8) Uani 1 1 d . . . . .
C6 C 1.2223(7) 0.1660(4) 0.4753(2) 0.0591(9) Uani 1 1 d . . . . .
H6 H 1.3713 0.1466 0.4309 0.071 Uiso 1 1 calc R U . . .
C7 C 1.1536(7) 0.0473(4) 0.5344(2) 0.0580(9) Uani 1 1 d . . . . .
H7 H 1.2582 -0.0497 0.5292 0.070 Uiso 1 1 calc R U . . .
C8 C 0.9319(6) 0.0737(3) 0.6001(2) 0.0504(8) Uani 1 1 d . . . . .
C9 C 0.7724(6) 0.2214(3) 0.6080(2) 0.0479(8) Uani 1 1 d . . . . .
C10 C 0.5435(6) 0.2508(3) 0.6741(2) 0.0510(8) Uani 1 1 d . . . . .
C11 C 0.3914(7) 0.3952(4) 0.6811(2) 0.0562(8) Uani 1 1 d . . . . .
H11 H 0.2402 0.4139 0.7248 0.067 Uiso 1 1 calc R U . . .
C12 C 0.4635(7) 0.5146(3) 0.6225(2) 0.0561(8) Uani 1 1 d . . . . .
H12 H 0.3605 0.6121 0.6279 0.067 Uiso 1 1 calc R U . . .
C13 C 0.8612(7) -0.0509(4) 0.6634(2) 0.0586(9) Uani 1 1 d . . . . .
C14 C 0.4619(7) 0.1235(4) 0.7341(2) 0.0581(9) Uani 1 1 d . . . . .
C15 C 1.0651(8) 0.7067(4) 0.3712(3) 0.0635(9) Uani 1 1 d . . . . .
H15A H 1.2601 0.6833 0.3490 0.076 Uiso 1 1 calc R U . . .
H15B H 1.0468 0.7999 0.4087 0.076 Uiso 1 1 calc R U . . .
C16 C 0.8860(8) 0.7371(4) 0.2874(3) 0.0646(8) Uani 1 1 d . . . . .
H16 H 0.6908 0.7582 0.3122 0.077 Uiso 1 1 calc R U . . .
C17 C 0.9041(14) 0.5998(5) 0.2238(3) 0.0997(14) Uani 1 1 d . . . . .
H17A H 0.7937 0.6261 0.1719 0.150 Uiso 1 1 calc R U . . .
H17B H 0.8346 0.5158 0.2569 0.150 Uiso 1 1 calc R U . . .
H17C H 1.0956 0.5697 0.2019 0.150 Uiso 1 1 calc R U . . .
C18 C 0.9579(7) 0.8835(3) 0.2414(2) 0.0632(8) Uani 1 1 d G . . . .
C19 C 1.1617(9) 0.8815(4) 0.1685(3) 0.126(2) Uani 1 1 d G . . . .
H19 H 1.2547 0.7880 0.1456 0.151 Uiso 1 1 calc R U . . .
C20 C 1.2265(11) 1.0192(4) 0.1298(3) 0.162(3) Uani 1 1 d G . . . .
H20 H 1.3629 1.0178 0.0811 0.195 Uiso 1 1 calc R U . . .
C21 C 1.0875(12) 1.1590(4) 0.1641(4) 0.122(2) Uani 1 1 d G . . . .
H21 H 1.1308 1.2511 0.1382 0.147 Uiso 1 1 calc R U . . .
C22 C 0.8837(11) 1.1610(3) 0.2369(4) 0.137(3) Uani 1 1 d G . . . .
H22 H 0.7907 1.2545 0.2598 0.164 Uiso 1 1 calc R U . . .
C23 C 0.8189(9) 1.0233(4) 0.2756(3) 0.129(3) Uani 1 1 d G . . . .
H23 H 0.6825 1.0246 0.3244 0.154 Uiso 1 1 calc R U . . .
C24 C 0.5581(8) -0.1434(4) 0.7878(3) 0.0686(10) Uani 1 1 d . . . . .
H24A H 0.6104 -0.2417 0.7561 0.082 Uiso 1 1 calc R U . . .
H24B H 0.3574 -0.1311 0.8025 0.082 Uiso 1 1 calc R U . . .
C25 C 0.7051(11) -0.1444(5) 0.8765(3) 0.0837(11) Uani 1 1 d . . . . .
H25A H 0.6577 -0.0447 0.9069 0.100 Uiso 1 1 calc R U . . .
H25B H 0.9057 -0.1598 0.8617 0.100 Uiso 1 1 calc R U . . .
C26 C 0.6276(14) -0.2696(7) 0.9429(4) 0.1061(16) Uani 1 1 d . . . . .
H26A H 0.7165 -0.2582 1.0003 0.127 Uiso 1 1 calc R U . . .
H26B H 0.4268 -0.2530 0.9573 0.127 Uiso 1 1 calc R U . . .
C27 C 0.7063(19) -0.4310(7) 0.9089(5) 0.1192(18) Uani 1 1 d D U . . .
C28 C 0.625(3) -0.5438(10) 0.9865(7) 0.116(2) Uani 0.7 1 d D U P A 1
H28A H 0.7337 -0.5325 1.0395 0.139 Uiso 0.7 1 calc R U P A 1
H28B H 0.4286 -0.5180 1.0064 0.139 Uiso 0.7 1 calc R U P A 1
C29 C 0.677(3) -0.7064(12) 0.9529(7) 0.130(3) Uani 0.7 1 d D U P A 1
H29A H 0.5820 -0.7157 0.8973 0.195 Uiso 0.7 1 calc R U P A 1
H29B H 0.6076 -0.7726 0.9997 0.195 Uiso 0.7 1 calc R U P A 1
H29C H 0.8741 -0.7358 0.9401 0.195 Uiso 0.7 1 calc R U P A 1
C28' C 0.816(7) -0.573(3) 0.956(3) 0.162(13) Uani 0.3 1 d D . P A 2
H28C H 0.9184 -0.5535 1.0093 0.195 Uiso 0.3 1 calc R U P A 2
H28D H 0.9292 -0.6470 0.9145 0.195 Uiso 0.3 1 calc R U P A 2
C29' C 0.530(8) -0.621(4) 0.984(3) 0.177(15) Uani 0.3 1 d D . P A 2
H29D H 0.4005 -0.5303 0.9986 0.265 Uiso 0.3 1 d R U P A 2
H29E H 0.5437 -0.6867 1.0368 0.265 Uiso 0.3 1 d R U P A 2
H29F H 0.4654 -0.6753 0.9332 0.265 Uiso 0.3 1 d R U P A 2
H27A H 0.903(8) -0.416(10) 0.901(6) 0.16(3) Uiso 1 1 d D . . . .
H27B H 0.60(3) -0.443(18) 0.854(7) 0.28(7) Uiso 1 1 d 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 C2 1.394(4) . ?
N1 C1 1.401(5) . ?
N1 C15 1.476(5) . ?
N2 C14 1.387(5) . ?
N2 C13 1.389(5) . ?
N2 C24 1.477(5) . ?
O1 C1 1.204(4) . ?
O2 C2 1.206(4) . ?
O3 C13 1.214(5) . ?
O4 C14 1.216(5) . ?
C1 C5 1.487(5) . ?
C2 C3 1.489(4) . ?
C3 C12 1.378(5) . ?
C3 C4 1.408(4) . ?
C4 C9 1.411(3) . ?
C4 C5 1.414(4) . ?
C5 C6 1.366(5) . ?
C6 C7 1.401(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.379(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.416(4) . ?
C8 C13 1.480(5) . ?
C9 C10 1.409(4) . ?
C10 C11 1.376(5) . ?
C10 C14 1.486(5) . ?
C11 C12 1.407(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C15 C16 1.538(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.503(6) . ?
C16 C18 1.510(4) . ?
C16 H16 0.9800 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.3900 . ?
C18 C23 1.3900 . ?
C19 C20 1.3900 . ?
C19 H19 0.9300 . ?
C20 C21 1.3900 . ?
C20 H20 0.9300 . ?
C21 C22 1.3900 . ?
C21 H21 0.9300 . ?
C22 C23 1.3900 . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 C25 1.506(6) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.521(6) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 C27 1.488(9) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C28' 1.47(3) . ?
C27 C28 1.556(10) . ?
C27 H27A 0.97(3) . ?
C27 H27B 0.99(3) . ?
C28 C29 1.487(13) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C28' C29' 1.52(3) . ?
C28' H28C 0.9700 . ?
C28' H28D 0.9700 . ?
C29' H29D 0.9600 . ?
C29' H29E 0.9600 . ?
C29' H29F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 125.1(3) . . ?
C2 N1 C15 116.7(3) . . ?
C1 N1 C15 118.1(3) . . ?
C14 N2 C13 125.0(3) . . ?
C14 N2 C24 118.0(3) . . ?
C13 N2 C24 117.0(3) . . ?
O1 C1 N1 121.0(3) . . ?
O1 C1 C5 122.1(3) . . ?
N1 C1 C5 116.9(3) . . ?
O2 C2 N1 120.6(3) . . ?
O2 C2 C3 122.2(3) . . ?
N1 C2 C3 117.2(3) . . ?
C12 C3 C4 120.4(3) . . ?
C12 C3 C2 120.0(3) . . ?
C4 C3 C2 119.5(3) . . ?
C3 C4 C9 119.2(2) . . ?
C3 C4 C5 121.6(3) . . ?
C9 C4 C5 119.3(2) . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 C1 120.2(3) . . ?
C4 C5 C1 119.5(3) . . ?
C5 C6 C7 120.9(3) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C8 C7 C6 120.3(3) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 119.9(3) . . ?
C7 C8 C13 120.4(3) . . ?
C9 C8 C13 119.7(3) . . ?
C10 C9 C4 119.7(2) . . ?
C10 C9 C8 120.9(3) . . ?
C4 C9 C8 119.4(2) . . ?
C11 C10 C9 120.2(3) . . ?
C11 C10 C14 120.3(3) . . ?
C9 C10 C14 119.6(3) . . ?
C10 C11 C12 120.3(3) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C3 C12 C11 120.2(3) . . ?
C3 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
O3 C13 N2 120.6(3) . . ?
O3 C13 C8 122.1(3) . . ?
N2 C13 C8 117.3(3) . . ?
O4 C14 N2 120.5(3) . . ?
O4 C14 C10 122.1(3) . . ?
N2 C14 C10 117.4(3) . . ?
N1 C15 C16 113.5(3) . . ?
N1 C15 H15A 108.9 . . ?
C16 C15 H15A 108.9 . . ?
N1 C15 H15B 108.9 . . ?
C16 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C17 C16 C18 115.1(3) . . ?
C17 C16 C15 113.0(3) . . ?
C18 C16 C15 108.1(2) . . ?
C17 C16 H16 106.7 . . ?
C18 C16 H16 106.7 . . ?
C15 C16 H16 106.7 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C23 120.0 . . ?
C19 C18 C16 121.9(2) . . ?
C23 C18 C16 118.1(2) . . ?
C18 C19 C20 120.0 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C21 120.0 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C22 C21 C20 120.0 . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C23 120.0 . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C22 C23 C18 120.0 . . ?
C22 C23 H23 120.0 . . ?
C18 C23 H23 120.0 . . ?
N2 C24 C25 112.0(3) . . ?
N2 C24 H24A 109.2 . . ?
C25 C24 H24A 109.2 . . ?
N2 C24 H24B 109.2 . . ?
C25 C24 H24B 109.2 . . ?
H24A C24 H24B 107.9 . . ?
C24 C25 C26 112.7(4) . . ?
C24 C25 H25A 109.0 . . ?
C26 C25 H25A 109.0 . . ?
C24 C25 H25B 109.0 . . ?
C26 C25 H25B 109.0 . . ?
H25A C25 H25B 107.8 . . ?
C27 C26 C25 115.7(5) . . ?
C27 C26 H26A 108.4 . . ?
C25 C26 H26A 108.4 . . ?
C27 C26 H26B 108.4 . . ?
C25 C26 H26B 108.4 . . ?
H26A C26 H26B 107.4 . . ?
C28' C27 C26 131.8(15) . . ?
C26 C27 C28 109.0(6) . . ?
C28' C27 H27A 84(5) . . ?
C26 C27 H27A 91(5) . . ?
C28 C27 H27A 117(5) . . ?
C28' C27 H27B 117(10) . . ?
C26 C27 H27B 107(10) . . ?
C28 C27 H27B 110(9) . . ?
H27A C27 H27B 121(10) . . ?
C29 C28 C27 111.1(9) . . ?
C29 C28 H28A 109.4 . . ?
C27 C28 H28A 109.4 . . ?
C29 C28 H28B 109.4 . . ?
C27 C28 H28B 109.4 . . ?
H28A C28 H28B 108.0 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C27 C28' C29' 95(2) . . ?
C27 C28' H28C 112.7 . . ?
C29' C28' H28C 112.7 . . ?
C27 C28' H28D 112.7 . . ?
C29' C28' H28D 112.7 . . ?
H28C C28' H28D 110.2 . . ?
C28' C29' H29D 109.0 . . ?
C28' C29' H29E 109.3 . . ?
H29D C29' H29E 109.5 . . ?
C28' C29' H29F 110.2 . . ?
H29D C29' H29F 109.5 . . ?
H29E C29' H29F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 O1 -175.6(3) . . . . ?
C15 N1 C1 O1 0.4(5) . . . . ?
C2 N1 C1 C5 3.9(5) . . . . ?
C15 N1 C1 C5 179.9(3) . . . . ?
C1 N1 C2 O2 179.1(3) . . . . ?
C15 N1 C2 O2 3.2(5) . . . . ?
C1 N1 C2 C3 -0.7(4) . . . . ?
C15 N1 C2 C3 -176.6(3) . . . . ?
O2 C2 C3 C12 -0.6(5) . . . . ?
N1 C2 C3 C12 179.2(3) . . . . ?
O2 C2 C3 C4 178.2(3) . . . . ?
N1 C2 C3 C4 -2.0(4) . . . . ?
C12 C3 C4 C9 -0.1(4) . . . . ?
C2 C3 C4 C9 -178.9(2) . . . . ?
C12 C3 C4 C5 179.9(3) . . . . ?
C2 C3 C4 C5 1.1(4) . . . . ?
C3 C4 C5 C6 -179.8(3) . . . . ?
C9 C4 C5 C6 0.2(4) . . . . ?
C3 C4 C5 C1 2.3(4) . . . . ?
C9 C4 C5 C1 -177.7(2) . . . . ?
O1 C1 C5 C6 -3.1(5) . . . . ?
N1 C1 C5 C6 177.4(3) . . . . ?
O1 C1 C5 C4 174.8(3) . . . . ?
N1 C1 C5 C4 -4.7(4) . . . . ?
C4 C5 C6 C7 -0.7(5) . . . . ?
C1 C5 C6 C7 177.2(3) . . . . ?
C5 C6 C7 C8 0.6(5) . . . . ?
C6 C7 C8 C9 0.1(5) . . . . ?
C6 C7 C8 C13 -179.2(3) . . . . ?
C3 C4 C9 C10 0.4(3) . . . . ?
C5 C4 C9 C10 -179.6(3) . . . . ?
C3 C4 C9 C8 -179.6(3) . . . . ?
C5 C4 C9 C8 0.5(3) . . . . ?
C7 C8 C9 C10 179.5(3) . . . . ?
C13 C8 C9 C10 -1.2(4) . . . . ?
C7 C8 C9 C4 -0.6(4) . . . . ?
C13 C8 C9 C4 178.7(2) . . . . ?
C4 C9 C10 C11 -0.3(4) . . . . ?
C8 C9 C10 C11 179.7(3) . . . . ?
C4 C9 C10 C14 177.8(2) . . . . ?
C8 C9 C10 C14 -2.3(4) . . . . ?
C9 C10 C11 C12 -0.1(5) . . . . ?
C14 C10 C11 C12 -178.2(3) . . . . ?
C4 C3 C12 C11 -0.3(5) . . . . ?
C2 C3 C12 C11 178.5(3) . . . . ?
C10 C11 C12 C3 0.4(5) . . . . ?
C14 N2 C13 O3 177.7(3) . . . . ?
C24 N2 C13 O3 -1.4(6) . . . . ?
C14 N2 C13 C8 -1.5(5) . . . . ?
C24 N2 C13 C8 179.4(3) . . . . ?
C7 C8 C13 O3 3.3(5) . . . . ?
C9 C8 C13 O3 -176.1(3) . . . . ?
C7 C8 C13 N2 -177.6(3) . . . . ?
C9 C8 C13 N2 3.1(4) . . . . ?
C13 N2 C14 O4 177.2(3) . . . . ?
C24 N2 C14 O4 -3.7(6) . . . . ?
C13 N2 C14 C10 -1.9(5) . . . . ?
C24 N2 C14 C10 177.1(3) . . . . ?
C11 C10 C14 O4 2.7(5) . . . . ?
C9 C10 C14 O4 -175.3(3) . . . . ?
C11 C10 C14 N2 -178.1(3) . . . . ?
C9 C10 C14 N2 3.8(4) . . . . ?
C2 N1 C15 C16 -81.1(4) . . . . ?
C1 N1 C15 C16 102.7(4) . . . . ?
N1 C15 C16 C17 -59.6(5) . . . . ?
N1 C15 C16 C18 171.9(3) . . . . ?
C17 C16 C18 C19 -34.6(5) . . . . ?
C15 C16 C18 C19 92.8(4) . . . . ?
C17 C16 C18 C23 147.2(4) . . . . ?
C15 C16 C18 C23 -85.5(4) . . . . ?
C23 C18 C19 C20 0.0 . . . . ?
C16 C18 C19 C20 -178.3(3) . . . . ?
C18 C19 C20 C21 0.0 . . . . ?
C19 C20 C21 C22 0.0 . . . . ?
C20 C21 C22 C23 0.0 . . . . ?
C21 C22 C23 C18 0.0 . . . . ?
C19 C18 C23 C22 0.0 . . . . ?
C16 C18 C23 C22 178.3(3) . . . . ?
C14 N2 C24 C25 -90.2(4) . . . . ?
C13 N2 C24 C25 89.0(4) . . . . ?
N2 C24 C25 C26 178.1(4) . . . . ?
C24 C25 C26 C27 63.0(7) . . . . ?
C25 C26 C27 C28' 141.1(19) . . . . ?
C25 C26 C27 C28 177.4(7) . . . . ?
C28' C27 C28 C29 -50(2) . . . . ?
C26 C27 C28 C29 175.1(10) . . . . ?
C26 C27 C28' C29' 91(3) . . . . ?
C28 C27 C28' C29' 26(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C16 H16 O2 0.98 2.67 3.195(4) 113.9 .

_refine_diff_density_max         0.184
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.031

_shelxl_version_number           2013-4

