# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_190923b
_database_code_depnum_ccdc_archive 'CCDC 2013934'
loop_
_audit_author_name
_audit_author_address
'Xiao Cheng'
;Shandong University
China
;
_audit_update_record             
;
2020-07-03 deposited with the CCDC.	2020-12-04 downloaded from the CCDC.
;
_audit_creation_date             2020-02-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(C18 H17 N O2)'
_chemical_formula_sum            'C36 H34 N2 O4'
_chemical_formula_weight         558.65
_chemical_melting_point          ?
_chemical_oxdiff_usercomment     CNO
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'

_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                   8.3012(5)
_cell_length_b                   11.1023(4)
_cell_length_c                   15.8874(9)
_cell_angle_alpha                87.983(4)
_cell_angle_beta                 75.800(5)
_cell_angle_gamma                89.423(4)
_cell_volume                     1418.60(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6221
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.2470
_cell_measurement_theta_min      2.8320
_shelx_estimated_absorpt_T_max   0.935
_shelx_estimated_absorpt_T_min   0.876
_exptl_absorpt_coefficient_mu    0.680
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92261
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.25a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0959
_diffrn_reflns_av_unetI/netI     0.0940
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12605
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.073
_diffrn_reflns_theta_min         2.871
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00 -33.00   0.50    0.11    --  -48.45  70.00-119.00   64
  2  ω   -107.00 -37.00   0.50    0.11    --  -48.45 -70.00 108.00  140
  3  ω    -20.00  12.00   0.50    0.11    --  -48.45  70.00-119.00   64
  4  ω     31.00 106.00   0.50    0.11    --   48.45  70.00-119.00  150
  5  ω    -61.00  27.00   0.50    0.11    --  -48.45  19.00-120.00  176
  6  ω    -21.00  66.00   0.50    0.11    --   48.45 -70.00 108.00  174
  7  ω   -152.00-107.00   0.50    1.10    --  -86.25 -70.00 108.00   90
  8  ω    -76.00 -27.00   0.50    1.10    --  -86.25  70.00-119.00   98
  9  ω   -158.00-105.00   0.50    1.10    --  -86.25 -99.00-180.00  106
 10  ω     42.00 122.00   0.50    1.10    --  106.49 -70.00 108.00  160
 11  ω     88.00 173.00   0.50    1.10    --  106.49  70.00-119.00  170
 12  ω     34.00 109.00   0.50    1.10    --  106.49 -99.00 -60.00  150
 13  ω     45.00  71.00   0.50    1.10    --  106.49-125.00  60.00   52
 14  ω     76.00 116.00   0.50    1.10    --  106.49-125.00  60.00   80
 15  ω     34.00 108.00   0.50    1.10    --  106.49 -99.00 -90.00  148
 16  ω     35.00 109.00   0.50    1.10    --  106.49 -99.00 120.00  148
 17  ω     96.00 161.00   0.50    1.10    --  106.49  19.00-120.00  130
 18  ω     34.00 118.00   0.50    1.10    --  106.49 -38.00 -60.00  168
 19  ω     34.00 120.00   0.50    1.10    --  106.49 -38.00  90.00  172
 20  ω     31.00 119.00   0.50    1.10    --  106.49 -19.00-120.00  176
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0677001000
_diffrn_orient_matrix_UB_12      0.0466065000
_diffrn_orient_matrix_UB_13      -0.0771480000
_diffrn_orient_matrix_UB_21      0.0671889000
_diffrn_orient_matrix_UB_22      0.1266864000
_diffrn_orient_matrix_UB_23      0.0084636000
_diffrn_orient_matrix_UB_31      0.1659781000
_diffrn_orient_matrix_UB_32      -0.0325117000
_diffrn_orient_matrix_UB_33      -0.0631880000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3780
_reflns_number_total             4962
_reflns_odcompleteness_completeness 98.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         4962
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1035
_refine_ls_R_factor_gt           0.0664
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0580P)²+0.3552P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1404
_refine_ls_wR_factor_ref         0.1622
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C17(H17), C22(H22), C23(H23), C26(H26), C27(H27),
 C33(H33), C19(H19), C20(H20), C21(H21), C28(H28), C29(H29), C30(H30), C31(H31),
  C32(H32)
2.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C36(H36A,H36B,
 H36C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4553(2) 0.74792(15) 0.96317(11) 0.0716(5) Uani 1 1 d . . . . .
H1 H 0.4777 0.7220 0.9140 0.107 Uiso 1 1 calc GR . . . .
O2 O 0.4972(2) 0.73746(15) 0.80177(11) 0.0732(5) Uani 1 1 d . . . . .
N1 N 0.1779(3) 1.03972(19) 1.30044(13) 0.0646(5) Uani 1 1 d . . . . .
C1 C 0.2810(3) 1.00368(19) 0.76691(14) 0.0532(5) Uani 1 1 d . . . . .
C3 C 0.3521(3) 0.89910(18) 0.88524(14) 0.0510(5) Uani 1 1 d . . . . .
C5 C 0.2215(2) 0.99429(19) 1.21929(14) 0.0524(5) Uani 1 1 d . . . . .
C7 C 0.3714(3) 0.90173(19) 0.73518(14) 0.0536(5) Uani 1 1 d . . . . .
C10 C 0.3753(3) 0.85251(18) 0.96360(15) 0.0541(5) Uani 1 1 d . . . . .
C11 C 0.3198(3) 0.90258(18) 1.04946(14) 0.0507(5) Uani 1 1 d . . . . .
C12 C 0.2642(3) 1.01129(18) 0.86322(14) 0.0515(5) Uani 1 1 d . . . . .
H12A H 0.1483 1.0112 0.8949 0.062 Uiso 1 1 calc R . . . .
H12B H 0.3171 1.0834 0.8763 0.062 Uiso 1 1 calc R . . . .
C14 C 0.4166(3) 0.83644(19) 0.80746(15) 0.0555(5) Uani 1 1 d . . . . .
C15 C 0.3389(3) 0.83568(19) 1.12272(15) 0.0571(5) Uani 1 1 d . . . . .
H15 H 0.3860 0.7592 1.1153 0.069 Uiso 1 1 calc R . . . .
C16 C 0.1999(3) 1.0616(2) 1.14617(15) 0.0578(5) Uani 1 1 d . . . . .
H16 H 0.1519 1.1378 1.1534 0.069 Uiso 1 1 calc R . . . .
C17 C 0.2480(3) 1.01722(19) 1.06470(14) 0.0558(5) Uani 1 1 d . . . . .
H17 H 0.2327 1.0645 1.0178 0.067 Uiso 1 1 calc R . . . .
C22 C 0.2910(3) 0.8785(2) 1.20489(15) 0.0588(5) Uani 1 1 d . . . . .
H22 H 0.3046 0.8304 1.2518 0.071 Uiso 1 1 calc R . . . .
C23 C 0.4043(3) 0.8751(2) 0.64763(15) 0.0641(6) Uani 1 1 d . . . . .
H23 H 0.4647 0.8068 0.6268 0.077 Uiso 1 1 calc R . . . .
C25 C 0.1005(4) 1.1577(2) 1.31403(17) 0.0741(7) Uani 1 1 d . . . . .
H25A H 0.1718 1.2171 1.2785 0.111 Uiso 1 1 calc GR . . . .
H25B H 0.0828 1.1770 1.3740 0.111 Uiso 1 1 calc GR . . . .
H25C H -0.0042 1.1571 1.2985 0.111 Uiso 1 1 calc GR . . . .
C26 C 0.2211(3) 1.0809(2) 0.71118(16) 0.0635(6) Uani 1 1 d . . . . .
H26 H 0.1594 1.1488 0.7317 0.076 Uiso 1 1 calc R . . . .
C27 C 0.3448(3) 0.9529(3) 0.59280(16) 0.0715(7) Uani 1 1 d . . . . .
H27 H 0.3651 0.9367 0.5341 0.086 Uiso 1 1 calc R . . . .
C33 C 0.2557(3) 1.0541(3) 0.62370(17) 0.0716(7) Uani 1 1 d . . . . .
H33 H 0.2179 1.1057 0.5853 0.086 Uiso 1 1 calc R . . . .
C34 C 0.1978(4) 0.9695(3) 1.37563(16) 0.0780(7) Uani 1 1 d . . . . .
H34A H 0.1276 0.8997 1.3837 0.117 Uiso 1 1 calc GR . . . .
H34B H 0.1674 1.0176 1.4262 0.117 Uiso 1 1 calc GR . . . .
H34C H 0.3115 0.9445 1.3669 0.117 Uiso 1 1 calc GR . . . .
O3 O 0.8897(2) 0.68760(14) 0.49249(12) 0.0750(5) Uani 1 1 d . . . . .
O4 O 1.0337(3) 0.66256(15) 0.33401(12) 0.0763(5) Uani 1 1 d . . . . .
H4 H 1.0092 0.6902 0.3827 0.114 Uiso 1 1 calc GR . . . .
N2 N 1.1301(3) 0.3519(2) 0.00251(14) 0.0757(6) Uani 1 1 d . . . . .
C2 C 0.6708(3) 0.41163(19) 0.52765(14) 0.0526(5) Uani 1 1 d . . . . .
C4 C 0.8516(3) 0.51635(17) 0.41128(14) 0.0510(5) Uani 1 1 d . . . . .
C6 C 0.9999(3) 0.49909(19) 0.25141(15) 0.0551(5) Uani 1 1 d . . . . .
C8 C 0.8255(3) 0.58597(18) 0.48771(15) 0.0558(5) Uani 1 1 d . . . . .
C9 C 0.7121(3) 0.51941(18) 0.55901(15) 0.0537(5) Uani 1 1 d . . . . .
C13 C 0.7532(3) 0.40108(19) 0.43324(15) 0.0557(5) Uani 1 1 d . . . . .
H13A H 0.6716 0.3954 0.3991 0.067 Uiso 1 1 calc R . . . .
H13B H 0.8255 0.3311 0.4235 0.067 Uiso 1 1 calc R . . . .
C18 C 0.9561(3) 0.55717(18) 0.33534(15) 0.0554(5) Uani 1 1 d . . . . .
C19 C 0.9043(3) 0.4104(2) 0.22716(15) 0.0589(5) Uani 1 1 d . . . . .
H19 H 0.8088 0.3830 0.2669 0.071 Uiso 1 1 calc R . . . .
C20 C 0.5608(3) 0.3334(2) 0.58318(16) 0.0637(6) Uani 1 1 d . . . . .
H20 H 0.5314 0.2609 0.5635 0.076 Uiso 1 1 calc R . . . .
C21 C 0.9474(3) 0.3621(2) 0.14612(16) 0.0615(6) Uani 1 1 d . . . . .
H21 H 0.8794 0.3037 0.1322 0.074 Uiso 1 1 calc R . . . .
C24 C 1.0906(3) 0.3985(2) 0.08419(15) 0.0593(6) Uani 1 1 d . . . . .
C28 C 0.6471(3) 0.5505(2) 0.64488(16) 0.0626(6) Uani 1 1 d . . . . .
H28 H 0.6762 0.6227 0.6652 0.075 Uiso 1 1 calc R . . . .
C29 C 1.1435(3) 0.5338(2) 0.18949(17) 0.0685(6) Uani 1 1 d . . . . .
H29 H 1.2104 0.5930 0.2031 0.082 Uiso 1 1 calc R . . . .
C30 C 0.4963(3) 0.3651(2) 0.66791(17) 0.0694(6) Uani 1 1 d . . . . .
H30 H 0.4223 0.3133 0.7053 0.083 Uiso 1 1 calc R . . . .
C31 C 0.5390(3) 0.4721(2) 0.69868(17) 0.0676(6) Uani 1 1 d . . . . .
H31 H 0.4941 0.4911 0.7563 0.081 Uiso 1 1 calc R . . . .
C32 C 1.1900(3) 0.4841(2) 0.10944(17) 0.0703(6) Uani 1 1 d . . . . .
H32 H 1.2894 0.5077 0.0713 0.084 Uiso 1 1 calc R . . . .
C35 C 1.0157(4) 0.2744(3) -0.02431(18) 0.0797(8) Uani 1 1 d . . . . .
H35A H 1.0031 0.2007 0.0101 0.120 Uiso 1 1 calc GR . . . .
H35B H 1.0579 0.2569 -0.0845 0.120 Uiso 1 1 calc GR . . . .
H35C H 0.9099 0.3138 -0.0165 0.120 Uiso 1 1 calc GR . . . .
C36 C 1.2741(4) 0.3950(3) -0.06218(19) 0.0880(9) Uani 1 1 d . . . . .
H36A H 1.2642 0.4803 -0.0719 0.132 Uiso 1 1 calc GR . . . .
H36B H 1.2813 0.3548 -0.1155 0.132 Uiso 1 1 calc GR . . . .
H36C H 1.3724 0.3785 -0.0422 0.132 Uiso 1 1 calc GR . . . .


_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 H1 0.8200 . ?
O1 C10 1.331(2) . ?
O2 C14 1.275(3) . ?
N1 C5 1.364(3) . ?
N1 C25 1.453(3) . ?
N1 C34 1.446(3) . ?
C1 C7 1.391(3) . ?
C1 C12 1.507(3) . ?
C1 C26 1.386(3) . ?
C3 C10 1.387(3) . ?
C3 C12 1.511(3) . ?
C3 C14 1.423(3) . ?
C5 C16 1.407(3) . ?
C5 C22 1.407(3) . ?
C7 C14 1.460(3) . ?
C7 C23 1.392(3) . ?
C10 C11 1.457(3) . ?
C11 C15 1.400(3) . ?
C11 C17 1.403(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C15 H15 0.9300 . ?
C15 C22 1.369(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.366(3) . ?
C17 H17 0.9300 . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C23 C27 1.378(4) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26 0.9300 . ?
C26 C33 1.391(4) . ?
C27 H27 0.9300 . ?
C27 C33 1.377(4) . ?
C33 H33 0.9300 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
O3 C8 1.266(3) . ?
O4 H4 0.8200 . ?
O4 C18 1.338(3) . ?
N2 C24 1.376(3) . ?
N2 C35 1.437(4) . ?
N2 C36 1.445(4) . ?
C2 C9 1.390(3) . ?
C2 C13 1.496(3) . ?
C2 C20 1.391(3) . ?
C4 C8 1.433(3) . ?
C4 C13 1.509(3) . ?
C4 C18 1.367(3) . ?
C6 C18 1.464(3) . ?
C6 C19 1.393(3) . ?
C6 C29 1.394(3) . ?
C8 C9 1.465(3) . ?
C9 C28 1.393(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C19 H19 0.9300 . ?
C19 C21 1.375(3) . ?
C20 H20 0.9300 . ?
C20 C30 1.378(3) . ?
C21 H21 0.9300 . ?
C21 C24 1.397(3) . ?
C24 C32 1.397(4) . ?
C28 H28 0.9300 . ?
C28 C31 1.371(4) . ?
C29 H29 0.9300 . ?
C29 C32 1.369(4) . ?
C30 H30 0.9300 . ?
C30 C31 1.382(4) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 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
C10 O1 H1 109.5 . . ?
C5 N1 C25 120.5(2) . . ?
C5 N1 C34 121.2(2) . . ?
C34 N1 C25 118.2(2) . . ?
C7 C1 C12 110.46(18) . . ?
C26 C1 C7 120.1(2) . . ?
C26 C1 C12 129.5(2) . . ?
C10 C3 C12 131.63(19) . . ?
C10 C3 C14 119.84(19) . . ?
C14 C3 C12 108.53(18) . . ?
N1 C5 C16 121.4(2) . . ?
N1 C5 C22 121.6(2) . . ?
C22 C5 C16 117.05(19) . . ?
C1 C7 C14 108.53(18) . . ?
C1 C7 C23 121.3(2) . . ?
C23 C7 C14 130.2(2) . . ?
O1 C10 C3 117.96(19) . . ?
O1 C10 C11 113.85(19) . . ?
C3 C10 C11 128.17(18) . . ?
C15 C11 C10 119.85(19) . . ?
C15 C11 C17 116.18(19) . . ?
C17 C11 C10 123.96(19) . . ?
C1 C12 C3 103.36(16) . . ?
C1 C12 H12A 111.1 . . ?
C1 C12 H12B 111.1 . . ?
C3 C12 H12A 111.1 . . ?
C3 C12 H12B 111.1 . . ?
H12A C12 H12B 109.1 . . ?
O2 C14 C3 125.7(2) . . ?
O2 C14 C7 125.2(2) . . ?
C3 C14 C7 109.09(18) . . ?
C11 C15 H15 118.7 . . ?
C22 C15 C11 122.5(2) . . ?
C22 C15 H15 118.7 . . ?
C5 C16 H16 119.4 . . ?
C17 C16 C5 121.2(2) . . ?
C17 C16 H16 119.4 . . ?
C11 C17 H17 118.9 . . ?
C16 C17 C11 122.2(2) . . ?
C16 C17 H17 118.9 . . ?
C5 C22 H22 119.6 . . ?
C15 C22 C5 120.8(2) . . ?
C15 C22 H22 119.6 . . ?
C7 C23 H23 121.0 . . ?
C27 C23 C7 118.1(2) . . ?
C27 C23 H23 121.0 . . ?
N1 C25 H25A 109.5 . . ?
N1 C25 H25B 109.5 . . ?
N1 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C1 C26 H26 120.9 . . ?
C1 C26 C33 118.2(2) . . ?
C33 C26 H26 120.9 . . ?
C23 C27 H27 119.5 . . ?
C33 C27 C23 120.9(2) . . ?
C33 C27 H27 119.5 . . ?
C26 C33 H33 119.3 . . ?
C27 C33 C26 121.4(2) . . ?
C27 C33 H33 119.3 . . ?
N1 C34 H34A 109.5 . . ?
N1 C34 H34B 109.5 . . ?
N1 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C18 O4 H4 109.5 . . ?
C24 N2 C35 120.5(2) . . ?
C24 N2 C36 120.5(3) . . ?
C35 N2 C36 118.3(2) . . ?
C9 C2 C13 111.24(19) . . ?
C9 C2 C20 119.2(2) . . ?
C20 C2 C13 129.5(2) . . ?
C8 C4 C13 108.87(19) . . ?
C18 C4 C8 120.29(19) . . ?
C18 C4 C13 130.8(2) . . ?
C19 C6 C18 124.1(2) . . ?
C19 C6 C29 116.1(2) . . ?
C29 C6 C18 119.9(2) . . ?
O3 C8 C4 125.6(2) . . ?
O3 C8 C9 126.0(2) . . ?
C4 C8 C9 108.37(18) . . ?
C2 C9 C8 108.35(19) . . ?
C2 C9 C28 121.6(2) . . ?
C28 C9 C8 130.0(2) . . ?
C2 C13 C4 103.17(17) . . ?
C2 C13 H13A 111.1 . . ?
C2 C13 H13B 111.1 . . ?
C4 C13 H13A 111.1 . . ?
C4 C13 H13B 111.1 . . ?
H13A C13 H13B 109.1 . . ?
O4 C18 C4 118.8(2) . . ?
O4 C18 C6 112.8(2) . . ?
C4 C18 C6 128.4(2) . . ?
C6 C19 H19 119.1 . . ?
C21 C19 C6 121.8(2) . . ?
C21 C19 H19 119.1 . . ?
C2 C20 H20 120.6 . . ?
C30 C20 C2 118.8(2) . . ?
C30 C20 H20 120.6 . . ?
C19 C21 H21 119.2 . . ?
C19 C21 C24 121.6(2) . . ?
C24 C21 H21 119.2 . . ?
N2 C24 C21 121.2(2) . . ?
N2 C24 C32 122.2(2) . . ?
C32 C24 C21 116.7(2) . . ?
C9 C28 H28 120.8 . . ?
C31 C28 C9 118.3(2) . . ?
C31 C28 H28 120.8 . . ?
C6 C29 H29 118.7 . . ?
C32 C29 C6 122.7(2) . . ?
C32 C29 H29 118.7 . . ?
C20 C30 H30 119.2 . . ?
C20 C30 C31 121.6(2) . . ?
C31 C30 H30 119.2 . . ?
C28 C31 C30 120.5(2) . . ?
C28 C31 H31 119.8 . . ?
C30 C31 H31 119.8 . . ?
C24 C32 H32 119.5 . . ?
C29 C32 C24 121.0(2) . . ?
C29 C32 H32 119.5 . . ?
N2 C35 H35A 109.5 . . ?
N2 C35 H35B 109.5 . . ?
N2 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
N2 C36 H36A 109.5 . . ?
N2 C36 H36B 109.5 . . ?
N2 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.005
_oxdiff_exptl_absorpt_empirical_full_min 0.566
####################################################################### 
# 
# 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_191202b
_database_code_depnum_ccdc_archive 'CCDC 2013935'
loop_
_audit_author_name
_audit_author_address
'Xiao Cheng'
;Shandong University
China
;
_audit_update_record             
;
2020-07-03 deposited with the CCDC.	2020-12-04 downloaded from the CCDC.
;
_audit_creation_date             2019-12-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C28 H21 N O2'
_chemical_formula_sum            'C28 H21 N O2'
_chemical_formula_weight         403.46
_chemical_melting_point          ?
_chemical_oxdiff_usercomment     CNO
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'

_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                   12.3705(3)
_cell_length_b                   9.7920(2)
_cell_length_c                   17.2120(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.237(2)
_cell_angle_gamma                90
_cell_volume                     2037.55(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5358
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.8430
_cell_measurement_theta_min      3.6220
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59136
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.25a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11306
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.080
_diffrn_reflns_theta_min         3.656
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -122.00 -52.00   1.00    0.16    --  -48.45  -9.00 179.00   70
  2  ω    -62.00  26.00   1.00    0.16    --  -48.45   9.00  -5.00   88
  3  ω     51.00 123.00   1.00    0.16    --   48.45   9.00  -5.00   72
  4  ω    -18.00  20.00   1.00    0.16    --   48.45  -9.00 179.00   38
  5  ω   -116.00 -72.00   1.00    1.20    --  -86.25  -9.00 179.00   44
  6  ω    -81.00 -55.00   1.00    1.20    --  -86.25   9.00  -5.00   26
  7  ω     33.00  97.00   1.00    1.20    --  106.49  -9.00 179.00   64
  8  ω     88.00 177.00   1.00    1.20    --  106.49   9.00  -5.00   89
  9  ω   -101.00 -14.00   1.00    1.20    --  -86.25  57.00-150.00   87
 10  ω     41.00 119.00   1.00    1.20    --  106.49 -19.00 -30.00   78
 11  ω     51.00 129.00   1.00    1.20    --  106.49 -77.00 -90.00   78
 12  ω     37.00 109.00   1.00    1.20    --  106.49 -99.00-150.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1263197000
_diffrn_orient_matrix_UB_12      -0.0009682000
_diffrn_orient_matrix_UB_13      0.0314124000
_diffrn_orient_matrix_UB_21      -0.0172752000
_diffrn_orient_matrix_UB_22      -0.0170074000
_diffrn_orient_matrix_UB_23      0.0854983000
_diffrn_orient_matrix_UB_31      0.0011461000
_diffrn_orient_matrix_UB_32      -0.1563413000
_diffrn_orient_matrix_UB_33      -0.0095003000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2890
_reflns_number_total             3598
_reflns_odcompleteness_completeness 98.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3598
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0437
_refine_ls_restrained_S_all      1.076
_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)+(0.0400P)²+0.7370P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1085
_refine_ls_wR_factor_ref         0.1223
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C11(H11), C12(H12), C13(H13), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26),
  C27(H27), C28(H28)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.79725(11) 0.52352(15) 0.53048(9) 0.0627(4) Uani 1 1 d . . . . .
O2 O 0.66709(12) 0.32513(14) 0.53641(10) 0.0639(4) Uani 1 1 d . . . . .
H2 H 0.7197 0.3691 0.5277 0.096 Uiso 1 1 calc GR . . . .
N1 N 0.24189(12) 0.10772(15) 0.64316(10) 0.0529(4) Uani 1 1 d . . . . .
C1 C 0.63770(14) 0.53818(19) 0.58950(10) 0.0454(4) Uani 1 1 d . . . . .
C2 C 0.51211(14) 0.33111(18) 0.59350(10) 0.0444(4) Uani 1 1 d . . . . .
C3 C 0.73483(14) 0.59016(19) 0.56570(11) 0.0482(4) Uani 1 1 d . . . . .
C4 C 0.60648(15) 0.40412(19) 0.57422(11) 0.0471(4) Uani 1 1 d . . . . .
C5 C 0.33227(14) 0.18101(18) 0.62773(11) 0.0454(4) Uani 1 1 d . . . . .
C6 C 0.43916(15) 0.38835(19) 0.63617(11) 0.0483(4) Uani 1 1 d . . . . .
H6 H 0.4496 0.4783 0.6534 0.058 Uiso 1 1 calc R . . . .
C7 C 0.14714(15) 0.17467(18) 0.66028(11) 0.0475(4) Uani 1 1 d . . . . .
C8 C 0.24057(15) -0.03824(19) 0.64205(11) 0.0478(4) Uani 1 1 d . . . . .
C9 C 0.66115(15) 0.77255(19) 0.62283(10) 0.0478(4) Uani 1 1 d . . . . .
C10 C 0.74817(14) 0.7341(2) 0.58850(11) 0.0483(4) Uani 1 1 d . . . . .
C11 C 0.35225(15) 0.31512(18) 0.65336(11) 0.0478(4) Uani 1 1 d . . . . .
H11 H 0.3060 0.3561 0.6827 0.057 Uiso 1 1 calc R . . . .
C12 C 0.40466(15) 0.12198(19) 0.58524(11) 0.0506(4) Uani 1 1 d . . . . .
H12 H 0.3936 0.0323 0.5676 0.061 Uiso 1 1 calc R . . . .
C13 C 0.49227(15) 0.19564(19) 0.56932(11) 0.0492(4) Uani 1 1 d . . . . .
H13 H 0.5399 0.1537 0.5415 0.059 Uiso 1 1 calc R . . . .
C14 C 0.58514(15) 0.65308(18) 0.62717(11) 0.0483(4) Uani 1 1 d . . . . .
H14A H 0.5827 0.6319 0.6818 0.058 Uiso 1 1 calc R . . . .
H14B H 0.5107 0.6716 0.5976 0.058 Uiso 1 1 calc R . . . .
C15 C 0.32147(17) -0.1120(2) 0.69223(12) 0.0551(5) Uani 1 1 d . . . . .
H15 H 0.3789 -0.0665 0.7259 0.066 Uiso 1 1 calc R . . . .
C16 C 0.15584(17) -0.1072(2) 0.59243(13) 0.0580(5) Uani 1 1 d . . . . .
H16 H 0.1006 -0.0588 0.5584 0.070 Uiso 1 1 calc R . . . .
C17 C 0.83034(17) 0.8265(2) 0.57982(13) 0.0600(5) Uani 1 1 d . . . . .
H17 H 0.8889 0.7994 0.5573 0.072 Uiso 1 1 calc R . . . .
C18 C 0.65398(18) 0.9061(2) 0.64766(12) 0.0584(5) Uani 1 1 d . . . . .
H18 H 0.5955 0.9335 0.6702 0.070 Uiso 1 1 calc R . . . .
C19 C 0.09800(17) 0.2839(2) 0.61514(13) 0.0600(5) Uani 1 1 d . . . . .
H19 H 0.1283 0.3181 0.5740 0.072 Uiso 1 1 calc R . . . .
C20 C 0.10165(18) 0.1265(2) 0.72170(13) 0.0613(5) Uani 1 1 d . . . . .
H20 H 0.1355 0.0547 0.7531 0.074 Uiso 1 1 calc R . . . .
C21 C 0.3178(2) -0.2525(2) 0.69281(14) 0.0646(6) Uani 1 1 d . . . . .
H21 H 0.3726 -0.3016 0.7268 0.078 Uiso 1 1 calc R . . . .
C22 C 0.73504(19) 0.9983(2) 0.63841(13) 0.0670(6) Uani 1 1 d . . . . .
H22 H 0.7306 1.0883 0.6547 0.080 Uiso 1 1 calc R . . . .
C23 C 0.15297(19) -0.2482(2) 0.59328(16) 0.0710(6) Uani 1 1 d . . . . .
H23 H 0.0959 -0.2943 0.5596 0.085 Uiso 1 1 calc R . . . .
C24 C 0.82301(19) 0.9581(2) 0.60512(14) 0.0673(6) Uani 1 1 d . . . . .
H24 H 0.8773 1.0211 0.6000 0.081 Uiso 1 1 calc R . . . .
C25 C 0.2333(2) -0.3201(2) 0.64323(16) 0.0713(7) Uani 1 1 d . . . . .
H25 H 0.2308 -0.4150 0.6437 0.086 Uiso 1 1 calc R . . . .
C26 C 0.00340(19) 0.3418(3) 0.63178(18) 0.0796(7) Uani 1 1 d . . . . .
H26 H -0.0293 0.4161 0.6022 0.096 Uiso 1 1 calc R . . . .
C27 C 0.0070(2) 0.1838(3) 0.73668(18) 0.0822(8) Uani 1 1 d . . . . .
H27 H -0.0236 0.1499 0.7777 0.099 Uiso 1 1 calc R . . . .
C28 C -0.0427(2) 0.2905(3) 0.6917(2) 0.0905(9) Uani 1 1 d . . . . .
H28 H -0.1075 0.3282 0.7015 0.109 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.260(2) . ?
O2 H2 0.8200 . ?
O2 C4 1.338(2) . ?
N1 C5 1.400(2) . ?
N1 C7 1.427(2) . ?
N1 C8 1.429(2) . ?
C1 C3 1.442(2) . ?
C1 C4 1.378(3) . ?
C1 C14 1.512(3) . ?
C2 C4 1.466(2) . ?
C2 C6 1.396(2) . ?
C2 C13 1.396(3) . ?
C3 C10 1.463(3) . ?
C5 C11 1.391(2) . ?
C5 C12 1.396(3) . ?
C6 H6 0.9300 . ?
C6 C11 1.376(3) . ?
C7 C19 1.385(3) . ?
C7 C20 1.382(3) . ?
C8 C15 1.380(3) . ?
C8 C16 1.380(3) . ?
C9 C10 1.385(3) . ?
C9 C14 1.513(3) . ?
C9 C18 1.385(3) . ?
C10 C17 1.392(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.377(3) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15 0.9300 . ?
C15 C21 1.377(3) . ?
C16 H16 0.9300 . ?
C16 C23 1.381(3) . ?
C17 H17 0.9300 . ?
C17 C24 1.370(3) . ?
C18 H18 0.9300 . ?
C18 C22 1.383(3) . ?
C19 H19 0.9300 . ?
C19 C26 1.384(3) . ?
C20 H20 0.9300 . ?
C20 C27 1.371(3) . ?
C21 H21 0.9300 . ?
C21 C25 1.371(3) . ?
C22 H22 0.9300 . ?
C22 C24 1.390(3) . ?
C23 H23 0.9300 . ?
C23 C25 1.364(3) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C26 C28 1.375(4) . ?
C27 H27 0.9300 . ?
C27 C28 1.367(4) . ?
C28 H28 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O2 H2 109.5 . . ?
C5 N1 C7 121.83(15) . . ?
C5 N1 C8 121.14(15) . . ?
C7 N1 C8 117.03(14) . . ?
C3 C1 C14 108.60(15) . . ?
C4 C1 C3 119.92(16) . . ?
C4 C1 C14 131.45(16) . . ?
C6 C2 C4 123.91(17) . . ?
C6 C2 C13 116.48(16) . . ?
C13 C2 C4 119.61(16) . . ?
O1 C3 C1 125.89(18) . . ?
O1 C3 C10 125.60(17) . . ?
C1 C3 C10 108.50(16) . . ?
O2 C4 C1 118.70(16) . . ?
O2 C4 C2 112.55(16) . . ?
C1 C4 C2 128.76(16) . . ?
C11 C5 N1 121.27(16) . . ?
C11 C5 C12 117.81(17) . . ?
C12 C5 N1 120.91(17) . . ?
C2 C6 H6 119.1 . . ?
C11 C6 C2 121.71(17) . . ?
C11 C6 H6 119.1 . . ?
C19 C7 N1 121.41(17) . . ?
C20 C7 N1 119.13(18) . . ?
C20 C7 C19 119.44(19) . . ?
C15 C8 N1 120.70(17) . . ?
C15 C8 C16 119.09(18) . . ?
C16 C8 N1 120.18(17) . . ?
C10 C9 C14 111.00(16) . . ?
C18 C9 C10 119.63(18) . . ?
C18 C9 C14 129.37(18) . . ?
C9 C10 C3 108.80(16) . . ?
C9 C10 C17 121.37(19) . . ?
C17 C10 C3 129.83(18) . . ?
C5 C11 H11 119.4 . . ?
C6 C11 C5 121.23(17) . . ?
C6 C11 H11 119.4 . . ?
C5 C12 H12 119.8 . . ?
C13 C12 C5 120.45(18) . . ?
C13 C12 H12 119.8 . . ?
C2 C13 H13 118.9 . . ?
C12 C13 C2 122.30(17) . . ?
C12 C13 H13 118.9 . . ?
C1 C14 C9 103.06(15) . . ?
C1 C14 H14A 111.2 . . ?
C1 C14 H14B 111.2 . . ?
C9 C14 H14A 111.2 . . ?
C9 C14 H14B 111.2 . . ?
H14A C14 H14B 109.1 . . ?
C8 C15 H15 119.8 . . ?
C21 C15 C8 120.5(2) . . ?
C21 C15 H15 119.8 . . ?
C8 C16 H16 120.0 . . ?
C8 C16 C23 120.0(2) . . ?
C23 C16 H16 120.0 . . ?
C10 C17 H17 120.7 . . ?
C24 C17 C10 118.6(2) . . ?
C24 C17 H17 120.7 . . ?
C9 C18 H18 120.5 . . ?
C22 C18 C9 119.0(2) . . ?
C22 C18 H18 120.5 . . ?
C7 C19 H19 120.3 . . ?
C26 C19 C7 119.4(2) . . ?
C26 C19 H19 120.3 . . ?
C7 C20 H20 119.8 . . ?
C27 C20 C7 120.5(2) . . ?
C27 C20 H20 119.8 . . ?
C15 C21 H21 120.0 . . ?
C25 C21 C15 120.0(2) . . ?
C25 C21 H21 120.0 . . ?
C18 C22 H22 119.6 . . ?
C18 C22 C24 120.9(2) . . ?
C24 C22 H22 119.6 . . ?
C16 C23 H23 119.8 . . ?
C25 C23 C16 120.4(2) . . ?
C25 C23 H23 119.8 . . ?
C17 C24 C22 120.5(2) . . ?
C17 C24 H24 119.7 . . ?
C22 C24 H24 119.7 . . ?
C21 C25 H25 120.0 . . ?
C23 C25 C21 120.1(2) . . ?
C23 C25 H25 120.0 . . ?
C19 C26 H26 119.7 . . ?
C28 C26 C19 120.6(3) . . ?
C28 C26 H26 119.7 . . ?
C20 C27 H27 119.8 . . ?
C28 C27 C20 120.4(2) . . ?
C28 C27 H27 119.8 . . ?
C26 C28 H28 120.1 . . ?
C27 C28 C26 119.7(2) . . ?
C27 C28 H28 120.1 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.579
_oxdiff_exptl_absorpt_empirical_full_min 0.558
####################################################################### 
# 
# 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_191121a
_database_code_depnum_ccdc_archive 'CCDC 2013936'
loop_
_audit_author_name
_audit_author_address
'Xiao Cheng'
;Shandong University
China
;
_audit_update_record             
;
2020-07-03 deposited with the CCDC.	2020-12-04 downloaded from the CCDC.
;
_audit_creation_date             2019-11-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C28 H19 N O2'
_chemical_formula_sum            'C28 H19 N O2'
_chemical_formula_weight         401.44
_chemical_melting_point          ?
_chemical_oxdiff_usercomment     CNO
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'

_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                   5.53320(10)
_cell_length_b                   26.1823(7)
_cell_length_c                   14.0997(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.973(3)
_cell_angle_gamma                90
_cell_volume                     2042.36(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3837
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.4070
_cell_measurement_theta_min      3.3500
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.956
_exptl_absorpt_coefficient_mu    0.648
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.23848
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.25a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0925
_diffrn_reflns_av_unetI/netI     0.0926
_diffrn_reflns_Laue_measured_fraction_full 0.928
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10947
_diffrn_reflns_point_group_measured_fraction_full 0.928
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.025
_diffrn_reflns_theta_min         3.376
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.928
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -92.00 -57.00   1.00    0.15    --  -48.45-145.00-121.00   35
  2  ω    -54.00 -10.00   1.00    0.15    --  -48.45 126.00 123.00   44
  3  ω    -98.00 -73.00   1.00    0.15    --  -48.45-126.00  45.00   25
  4  ω    -90.00 -60.00   1.00    0.15    --  -48.45 126.00 123.00   30
  5  ω     51.00  76.00   1.00    0.15    --   48.45-145.00-121.00   25
  6  ω     32.00  97.00   1.00    0.15    --   48.45-126.00  45.00   65
  7  ω    -88.00 -33.00   1.00    1.40    --  -86.25 126.00 123.00   55
  8  ω    -96.00 -60.00   1.00    1.40    --  -86.25-145.00-121.00   36
  9  ω     42.00  79.00   1.00    1.40    --  106.49-126.00  45.00   37
 10  ω     90.00 117.00   1.00    1.40    --  106.49 145.00 -69.00   27
 11  ω     82.00 131.00   1.00    1.40    --  106.49-145.00-121.00   49
 12  ω     87.00 118.00   1.00    1.40    --  106.49-126.00  45.00   31
 13  ω   -120.00 -27.00   1.00    0.15    --  -48.45 -77.00-120.00   93
 14  ω   -139.00-114.00   1.00    1.40    --  -86.25-126.00  45.00   25
 15  ω     34.00 120.00   1.00    1.40    --  106.49 -38.00   0.00   86
 16  ω     90.00 121.00   1.00    1.40    --  106.49 -57.00   0.00   31
 17  ω     31.00 107.00   1.00    1.40    --  106.49 -19.00 150.00   76
 18  ω     34.00  62.00   1.00    1.40    --  106.49 -57.00   0.00   28
 19  ω    103.00 128.00   1.00    1.40    --  106.49 126.00 123.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0118147000
_diffrn_orient_matrix_UB_12      -0.0585093000
_diffrn_orient_matrix_UB_13      0.0108840000
_diffrn_orient_matrix_UB_21      -0.0184083000
_diffrn_orient_matrix_UB_22      0.0059824000
_diffrn_orient_matrix_UB_23      0.1082712000
_diffrn_orient_matrix_UB_31      -0.2776721000
_diffrn_orient_matrix_UB_32      0.0020784000
_diffrn_orient_matrix_UB_33      -0.0094836000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2549
_reflns_number_total             3430
_reflns_odcompleteness_completeness 93.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.388
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3430
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1459
_refine_ls_R_factor_gt           0.1222
_refine_ls_restrained_S_all      1.388
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3069
_refine_ls_wR_factor_ref         0.3520
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C19(H19), C20(H20),
 C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7932(6) 0.28511(12) 0.5138(2) 0.0715(10) Uani 1 1 d . . . . .
H1 H 0.8520 0.2576 0.5300 0.107 Uiso 1 1 calc GR . . . .
O2 O 1.1272(6) 0.21884(12) 0.52039(19) 0.0710(9) Uani 1 1 d . . . . .
N1 N 0.2205(6) 0.44603(12) 0.2630(2) 0.0559(9) Uani 1 1 d . . . . .
C1 C 0.6796(6) 0.33212(13) 0.3792(3) 0.0482(9) Uani 1 1 d . . . . .
C2 C 0.3747(6) 0.40808(13) 0.3039(3) 0.0506(9) Uani 1 1 d . . . . .
C3 C 1.3013(7) 0.22539(14) 0.2811(3) 0.0488(9) Uani 1 1 d . . . . .
C4 C 0.8359(6) 0.29317(14) 0.4227(2) 0.0478(9) Uani 1 1 d . . . . .
C5 C 1.0185(6) 0.26558(13) 0.3797(2) 0.0447(8) Uani 1 1 d . . . . .
C6 C 0.7086(7) 0.35040(15) 0.2874(3) 0.0547(10) Uani 1 1 d . . . . .
H6 H 0.8309 0.3368 0.2508 0.066 Uiso 1 1 calc R . . . .
C7 C 1.3259(7) 0.20389(14) 0.3704(3) 0.0498(9) Uani 1 1 d . . . . .
C8 C 0.1477(7) 0.49031(15) 0.3094(3) 0.0592(11) Uani 1 1 d . . . . .
C9 C 1.1074(6) 0.26610(13) 0.2795(2) 0.0464(9) Uani 1 1 d . . . . .
H9A H 1.1738 0.2992 0.2632 0.056 Uiso 1 1 calc R . . . .
H9B H 0.9786 0.2576 0.2347 0.056 Uiso 1 1 calc R . . . .
C10 C 0.0930(7) 0.44095(14) 0.1776(3) 0.0517(9) Uani 1 1 d . . . . .
C11 C 1.1534(7) 0.22862(14) 0.4341(3) 0.0514(9) Uani 1 1 d . . . . .
C12 C 0.1005(7) 0.40264(16) 0.1106(3) 0.0561(10) Uani 1 1 d . . . . .
H12 H 0.2063 0.3752 0.1175 0.067 Uiso 1 1 calc R . . . .
C13 C 0.5629(7) 0.38788(15) 0.2490(3) 0.0535(10) Uani 1 1 d . . . . .
H13 H 0.5880 0.3997 0.1878 0.064 Uiso 1 1 calc R . . . .
C14 C 0.3426(8) 0.39010(16) 0.3939(3) 0.0591(10) Uani 1 1 d . . . . .
H14 H 0.2176 0.4032 0.4299 0.071 Uiso 1 1 calc R . . . .
C15 C 0.4914(7) 0.35315(15) 0.4323(3) 0.0539(10) Uani 1 1 d . . . . .
H15 H 0.4672 0.3420 0.4940 0.065 Uiso 1 1 calc R . . . .
C16 C 1.4450(7) 0.20952(15) 0.2084(3) 0.0568(10) Uani 1 1 d . . . . .
H16 H 1.4303 0.2239 0.1483 0.068 Uiso 1 1 calc R . . . .
C17 C -0.0646(7) 0.48287(15) 0.1683(3) 0.0607(11) Uani 1 1 d . . . . .
C18 C -0.0334(7) 0.51400(15) 0.2515(3) 0.0636(11) Uani 1 1 d . . . . .
C19 C 1.4941(8) 0.16612(16) 0.3893(3) 0.0615(11) Uani 1 1 d . . . . .
H19 H 1.5101 0.1522 0.4497 0.074 Uiso 1 1 calc R . . . .
C20 C 1.6128(8) 0.17140(17) 0.2274(3) 0.0658(11) Uani 1 1 d . . . . .
H20 H 1.7115 0.1601 0.1790 0.079 Uiso 1 1 calc R . . . .
C21 C 1.6377(8) 0.14962(17) 0.3166(3) 0.0659(12) Uani 1 1 d . . . . .
H21 H 1.7510 0.1239 0.3273 0.079 Uiso 1 1 calc R . . . .
C22 C -0.2187(8) 0.4853(2) 0.0881(4) 0.0784(15) Uani 1 1 d . . . . .
H22 H -0.3266 0.5123 0.0805 0.094 Uiso 1 1 calc R . . . .
C23 C -0.0542(9) 0.4062(2) 0.0326(3) 0.0744(13) Uani 1 1 d . . . . .
H23 H -0.0550 0.3805 -0.0130 0.089 Uiso 1 1 calc R . . . .
C24 C -0.1328(10) 0.55992(18) 0.2821(4) 0.0815(16) Uani 1 1 d . . . . .
H24 H -0.2509 0.5762 0.2454 0.098 Uiso 1 1 calc R . . . .
C25 C 0.2260(9) 0.51210(18) 0.3931(4) 0.0761(13) Uani 1 1 d . . . . .
H25 H 0.3459 0.4967 0.4302 0.091 Uiso 1 1 calc R . . . .
C26 C -0.2082(10) 0.4478(2) 0.0219(4) 0.0852(15) Uani 1 1 d . . . . .
H26 H -0.3067 0.4500 -0.0320 0.102 Uiso 1 1 calc R . . . .
C27 C -0.0576(11) 0.58082(19) 0.3654(5) 0.0905(19) Uani 1 1 d . . . . .
H27 H -0.1265 0.6112 0.3860 0.109 Uiso 1 1 calc R . . . .
C28 C 0.1217(11) 0.55738(19) 0.4204(5) 0.0882(17) Uani 1 1 d . . . . .
H28 H 0.1722 0.5727 0.4769 0.106 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8200 . ?
O1 C4 1.327(4) . ?
O2 C11 1.254(4) . ?
N1 C2 1.425(5) . ?
N1 C8 1.394(5) . ?
N1 C10 1.392(5) . ?
C1 C4 1.465(5) . ?
C1 C6 1.391(5) . ?
C1 C15 1.405(5) . ?
C2 C13 1.410(5) . ?
C2 C14 1.369(6) . ?
C3 C7 1.384(5) . ?
C3 C9 1.512(5) . ?
C3 C16 1.373(5) . ?
C4 C5 1.390(5) . ?
C5 C9 1.504(4) . ?
C5 C11 1.436(5) . ?
C6 H6 0.9300 . ?
C6 C13 1.376(5) . ?
C7 C11 1.472(5) . ?
C7 C19 1.381(5) . ?
C8 C18 1.424(6) . ?
C8 C25 1.374(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C12 1.379(6) . ?
C10 C17 1.407(5) . ?
C12 H12 0.9300 . ?
C12 C23 1.385(6) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.375(6) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C16 C20 1.386(6) . ?
C17 C18 1.436(7) . ?
C17 C22 1.406(7) . ?
C18 C24 1.394(6) . ?
C19 H19 0.9300 . ?
C19 C21 1.377(6) . ?
C20 H20 0.9300 . ?
C20 C21 1.385(6) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C22 C26 1.357(8) . ?
C23 H23 0.9300 . ?
C23 C26 1.390(7) . ?
C24 H24 0.9300 . ?
C24 C27 1.354(9) . ?
C25 H25 0.9300 . ?
C25 C28 1.376(7) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C27 C28 1.392(9) . ?
C28 H28 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O1 H1 109.5 . . ?
C8 N1 C2 124.5(3) . . ?
C10 N1 C2 125.1(3) . . ?
C10 N1 C8 109.8(3) . . ?
C6 C1 C4 123.5(3) . . ?
C6 C1 C15 117.3(4) . . ?
C15 C1 C4 119.2(3) . . ?
C13 C2 N1 118.8(3) . . ?
C14 C2 N1 121.9(3) . . ?
C14 C2 C13 119.3(4) . . ?
C7 C3 C9 111.1(3) . . ?
C16 C3 C7 120.5(4) . . ?
C16 C3 C9 128.4(3) . . ?
O1 C4 C1 113.7(3) . . ?
O1 C4 C5 118.8(3) . . ?
C5 C4 C1 127.4(3) . . ?
C4 C5 C9 131.1(3) . . ?
C4 C5 C11 119.5(3) . . ?
C11 C5 C9 109.4(3) . . ?
C1 C6 H6 118.8 . . ?
C13 C6 C1 122.4(3) . . ?
C13 C6 H6 118.8 . . ?
C3 C7 C11 108.7(3) . . ?
C19 C7 C3 121.5(3) . . ?
C19 C7 C11 129.7(3) . . ?
N1 C8 C18 107.4(4) . . ?
C25 C8 N1 131.2(4) . . ?
C25 C8 C18 121.3(4) . . ?
C3 C9 H9A 111.2 . . ?
C3 C9 H9B 111.2 . . ?
C5 C9 C3 102.8(3) . . ?
C5 C9 H9A 111.2 . . ?
C5 C9 H9B 111.2 . . ?
H9A C9 H9B 109.1 . . ?
N1 C10 C17 108.1(4) . . ?
C12 C10 N1 129.9(3) . . ?
C12 C10 C17 122.0(4) . . ?
O2 C11 C5 126.0(3) . . ?
O2 C11 C7 126.1(3) . . ?
C5 C11 C7 107.9(3) . . ?
C10 C12 H12 121.0 . . ?
C10 C12 C23 118.0(4) . . ?
C23 C12 H12 121.0 . . ?
C2 C13 H13 120.5 . . ?
C6 C13 C2 119.0(3) . . ?
C6 C13 H13 120.5 . . ?
C2 C14 H14 119.3 . . ?
C2 C14 C15 121.4(4) . . ?
C15 C14 H14 119.3 . . ?
C1 C15 H15 119.7 . . ?
C14 C15 C1 120.7(3) . . ?
C14 C15 H15 119.7 . . ?
C3 C16 H16 121.0 . . ?
C3 C16 C20 117.9(4) . . ?
C20 C16 H16 121.0 . . ?
C10 C17 C18 107.5(4) . . ?
C22 C17 C10 118.5(4) . . ?
C22 C17 C18 133.9(4) . . ?
C8 C18 C17 107.2(3) . . ?
C24 C18 C8 118.4(5) . . ?
C24 C18 C17 134.4(5) . . ?
C7 C19 H19 120.8 . . ?
C21 C19 C7 118.4(4) . . ?
C21 C19 H19 120.8 . . ?
C16 C20 H20 119.1 . . ?
C21 C20 C16 121.9(4) . . ?
C21 C20 H20 119.1 . . ?
C19 C21 C20 119.8(4) . . ?
C19 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C17 C22 H22 120.4 . . ?
C26 C22 C17 119.2(4) . . ?
C26 C22 H22 120.4 . . ?
C12 C23 H23 119.7 . . ?
C12 C23 C26 120.5(5) . . ?
C26 C23 H23 119.7 . . ?
C18 C24 H24 120.0 . . ?
C27 C24 C18 120.0(5) . . ?
C27 C24 H24 120.0 . . ?
C8 C25 H25 121.0 . . ?
C8 C25 C28 118.1(5) . . ?
C28 C25 H25 121.0 . . ?
C22 C26 C23 121.8(5) . . ?
C22 C26 H26 119.1 . . ?
C23 C26 H26 119.1 . . ?
C24 C27 H27 119.7 . . ?
C24 C27 C28 120.7(5) . . ?
C28 C27 H27 119.7 . . ?
C25 C28 C27 121.5(6) . . ?
C25 C28 H28 119.2 . . ?
C27 C28 H28 119.2 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.701
_oxdiff_exptl_absorpt_empirical_full_min 0.315
