# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_exp_7350
_database_code_depnum_ccdc_archive 'CCDC 2225644'
loop_
_audit_author_name
_audit_author_address
'Pengyu Li'
;Beijing University of Chemical Technology
China
;
_audit_update_record             
;
2022-12-11 deposited with the CCDC.	2023-05-16 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT026_exp_7350            
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        30% Check
RESPONSE: 1
;
# Added during the CSD deposition process: Sunday 11 December 2022 07:48 AM
# end Validation Reply Form

_audit_creation_date             2022-09-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C22 H22 N2 O'
_chemical_formula_sum            'C22 H22 N2 O'
_chemical_formula_weight         330.41
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   11.9983(12)
_cell_length_b                   13.4817(16)
_cell_length_c                   13.8985(14)
_cell_angle_alpha                61.844(11)
_cell_angle_beta                 74.518(9)
_cell_angle_gamma                70.951(10)
_cell_volume                     1856.3(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    905
_cell_measurement_temperature    293.0(6)
_cell_measurement_theta_max      21.1190
_cell_measurement_theta_min      3.5230
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97032
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0774
_diffrn_reflns_av_unetI/netI     0.1369
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13865
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         3.007
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.0(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -10.00   28.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -10.8508  -99.0000  120.0000 38

#__ type_ start__ end____ width___ exp.time_
  2 omega  -43.00   24.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852  -19.0000   90.0000 67

#__ type_ start__ end____ width___ exp.time_
  3 omega    1.00   76.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852   57.0000   90.0000 75

#__ type_ start__ end____ width___ exp.time_
  4 omega    5.00   32.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852   57.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
  5 omega  -24.00   33.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852  -57.0000  -30.0000 57

#__ type_ start__ end____ width___ exp.time_
  6 omega  -24.00   52.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852  -99.0000  -90.0000 76

#__ type_ start__ end____ width___ exp.time_
  7 omega  -24.00    3.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852  -99.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
  8 omega   45.00   72.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852  178.0000 -150.0000 27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0081012000
_diffrn_orient_matrix_UB_12      0.0400469000
_diffrn_orient_matrix_UB_13      0.0155402000
_diffrn_orient_matrix_UB_21      0.0027619000
_diffrn_orient_matrix_UB_22      0.0412216000
_diffrn_orient_matrix_UB_23      -0.0558112000
_diffrn_orient_matrix_UB_31      -0.0625408000
_diffrn_orient_matrix_UB_32      0.0216269000
_diffrn_orient_matrix_UB_33      0.0075388000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1934
_reflns_number_total             6531
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.07
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'A short history of SHELX (Sheldrick, 2007)'
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0019(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     452
_refine_ls_number_reflns         6531
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.2461
_refine_ls_R_factor_gt           0.0762
_refine_ls_restrained_S_all      0.989
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0567P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1526
_refine_ls_wR_factor_ref         0.2469
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C43) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.04
3.a Ternary CH refined with riding coordinates:
 C17(H17), C39(H39)
3.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C19(H19A,H19B), C40(H40A,H40B), C22(H22A,H22B), C41(H41A,
 H41B), C42(H42A,H42B), C20(H20A,H20B), C21(H21A,H21B), C44(H44A,H44B),
 C43(H43A,H43B)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), C36(H36), C12(H12), C29(H29), C7(H7), C11(H11), C37(H37),
 C14(H14), C15(H15), C34(H34), C33(H33), C6(H6), C5(H5), C24(H24), C25(H25),
 C28(H28), C2(H2), C26(H26), C27(H27), C4(H4), C3(H3A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C35 C 0.6714(3) 0.5740(4) 0.1310(4) 0.0527(12) Uani 1 1 d . . . . .
C32 C 0.6075(4) 0.4460(4) 0.3563(4) 0.0529(12) Uani 1 1 d . . . . .
C10 C 0.1366(3) 0.5552(4) 0.1454(4) 0.0526(12) Uani 1 1 d . . . . .
C13 C 0.0742(3) 0.4226(4) 0.3683(4) 0.0547(12) Uani 1 1 d . . . . .
N1 N 0.1095(3) 0.3138(3) 0.5578(3) 0.0652(11) Uani 1 1 d . . . . .
H1 H 0.172906 0.339549 0.534850 0.078 Uiso 1 1 calc R U . . .
C16 C 0.0346(4) 0.3483(4) 0.4867(4) 0.0621(13) Uani 1 1 d . . . . .
C38 C 0.7108(4) 0.6458(4) 0.0125(4) 0.0635(13) Uani 1 1 d . . . . .
C30 C 0.5758(4) 0.3750(4) 0.4755(4) 0.0613(13) Uani 1 1 d . . . . .
N3 N 0.6337(3) 0.6880(4) -0.0597(3) 0.0756(12) Uani 1 1 d . . . . .
H3 H 0.566437 0.668964 -0.036227 0.091 Uiso 1 1 calc R U . . .
C8 C 0.1667(4) 0.6289(4) 0.0263(4) 0.0557(12) Uani 1 1 d . . . . .
C36 C 0.7413(3) 0.5475(4) 0.2083(4) 0.0550(12) Uani 1 1 d . . . . .
H36 H 0.811117 0.573233 0.184653 0.066 Uiso 1 1 calc R U . . .
C12 C 0.0326(4) 0.4158(4) 0.2885(4) 0.0618(13) Uani 1 1 d . . . . .
H12 H -0.017091 0.366597 0.309069 0.074 Uiso 1 1 calc R U . . .
O1 O -0.0609(3) 0.3224(3) 0.5130(3) 0.0928(12) Uani 1 1 d . . . . .
C29 C 0.6493(4) 0.3256(4) 0.5525(4) 0.0690(14) Uani 1 1 d . . . . .
H29 H 0.725308 0.338917 0.525213 0.083 Uiso 1 1 calc R U . . .
C7 C 0.0956(4) 0.6693(4) -0.0498(4) 0.0636(13) Uani 1 1 d . . . . .
H7 H 0.023102 0.648330 -0.022830 0.076 Uiso 1 1 calc R U . . .
C11 C 0.0643(4) 0.4814(4) 0.1788(4) 0.0600(13) Uani 1 1 d . . . . .
H11 H 0.035887 0.475461 0.126138 0.072 Uiso 1 1 calc R U . . .
C37 C 0.7113(4) 0.4850(4) 0.3183(4) 0.0626(13) Uani 1 1 d . . . . .
H37 H 0.760755 0.468437 0.367930 0.075 Uiso 1 1 calc R U . . .
O2 O 0.8105(3) 0.6649(3) -0.0161(3) 0.0915(12) Uani 1 1 d . . . . .
C1 C 0.1121(5) 0.7407(4) -0.1675(4) 0.0656(14) Uani 1 1 d . . . . .
C31 C 0.4566(4) 0.3569(4) 0.5053(4) 0.0690(14) Uani 1 1 d . . . . .
C17 C 0.0883(4) 0.2335(4) 0.6740(4) 0.0610(13) Uani 1 1 d . . . . .
H17 H 0.002163 0.242871 0.696206 0.073 Uiso 1 1 calc R U . . .
C14 C 0.1493(4) 0.4946(4) 0.3357(4) 0.0657(14) Uani 1 1 d . . . . .
H14 H 0.179868 0.498189 0.388548 0.079 Uiso 1 1 calc R U . . .
C39 C 0.6576(4) 0.7641(5) -0.1750(4) 0.0705(15) Uani 1 1 d . . . . .
H39 H 0.744123 0.749164 -0.196075 0.085 Uiso 1 1 calc R U . . .
C15 C 0.1799(3) 0.5618(4) 0.2251(4) 0.0647(14) Uani 1 1 d . . . . .
H15 H 0.229338 0.611361 0.204191 0.078 Uiso 1 1 calc R U . . .
C34 C 0.5674(4) 0.5350(4) 0.1682(4) 0.0637(14) Uani 1 1 d . . . . .
H34 H 0.518309 0.551491 0.118289 0.076 Uiso 1 1 calc R U . . .
C23 C 0.6313(4) 0.2553(4) 0.6702(4) 0.0685(14) Uani 1 1 d . . . . .
C9 C 0.2775(5) 0.6608(5) -0.0023(4) 0.0851(18) Uani 1 1 d . . . . .
C18 C 0.1367(4) 0.2599(4) 0.7459(4) 0.0727(14) Uani 1 1 d . . . . .
H18A H 0.097895 0.338140 0.738119 0.087 Uiso 1 1 calc R U . . .
H18B H 0.221229 0.255438 0.722191 0.087 Uiso 1 1 calc R U . . .
C33 C 0.5370(4) 0.4718(4) 0.2795(4) 0.0657(14) Uani 1 1 d . . . . .
H33 H 0.467242 0.445838 0.303494 0.079 Uiso 1 1 calc R U . . .
C6 C 0.2193(5) 0.7500(5) -0.2322(5) 0.0866(16) Uani 1 1 d . . . . .
H6 H 0.288422 0.707666 -0.199741 0.104 Uiso 1 1 calc R U . . .
C19 C 0.1172(5) 0.1756(6) 0.8662(4) 0.0957(18) Uani 1 1 d . . . . .
H19A H 0.153206 0.192163 0.910057 0.115 Uiso 1 1 calc R U . . .
H19B H 0.032541 0.185533 0.892112 0.115 Uiso 1 1 calc R U . . .
C5 C 0.2292(6) 0.8203(5) -0.3444(5) 0.0983(18) Uani 1 1 d . . . . .
H5 H 0.303719 0.825040 -0.386184 0.118 Uiso 1 1 calc R U . . .
C40 C 0.6059(5) 0.7419(5) -0.2464(4) 0.0915(17) Uani 1 1 d . . . . .
H40A H 0.520611 0.752088 -0.224115 0.110 Uiso 1 1 calc R U . . .
H40B H 0.639095 0.662253 -0.236443 0.110 Uiso 1 1 calc R U . . .
C24 C 0.5240(4) 0.2397(4) 0.7351(4) 0.0783(15) Uani 1 1 d . . . . .
H24 H 0.454238 0.277106 0.703106 0.094 Uiso 1 1 calc R U . . .
C25 C 0.5179(5) 0.1702(5) 0.8460(5) 0.0923(17) Uani 1 1 d . . . . .
H25 H 0.444286 0.161193 0.888265 0.111 Uiso 1 1 calc R U . . .
N2 N 0.3657(4) 0.6837(5) -0.0195(4) 0.130(2) Uani 1 1 d . . . . .
C28 C 0.7306(5) 0.2006(6) 0.7217(5) 0.127(3) Uani 1 1 d . . . . .
H28 H 0.804395 0.211584 0.680945 0.153 Uiso 1 1 calc R U . . .
C22 C 0.1413(7) 0.1126(5) 0.6875(5) 0.132(2) Uani 1 1 d . . . . .
H22A H 0.226050 0.102697 0.662207 0.158 Uiso 1 1 calc R U . . .
H22B H 0.105909 0.096574 0.642750 0.158 Uiso 1 1 calc R U . . .
N4 N 0.3639(4) 0.3447(5) 0.5203(4) 0.1122(19) Uani 1 1 d . . . . .
C41 C 0.6299(6) 0.8219(6) -0.3672(5) 0.115(2) Uani 1 1 d . . . . .
H41A H 0.714783 0.806318 -0.391948 0.138 Uiso 1 1 calc R U . . .
H41B H 0.590824 0.807278 -0.410395 0.138 Uiso 1 1 calc R U . . .
C42 C 0.5853(5) 0.9454(6) -0.3848(5) 0.123(2) Uani 1 1 d . . . . .
H42A H 0.499508 0.962966 -0.365680 0.148 Uiso 1 1 calc R U . . .
H42B H 0.604396 0.995509 -0.461792 0.148 Uiso 1 1 calc R U . . .
C2 C 0.0141(5) 0.8011(6) -0.2205(5) 0.120(3) Uani 1 1 d . . . . .
H2 H -0.060706 0.793776 -0.180355 0.144 Uiso 1 1 calc R U . . .
C26 C 0.6185(6) 0.1144(6) 0.8942(5) 0.116(2) Uani 1 1 d . . . . .
H26 H 0.614958 0.066131 0.969127 0.140 Uiso 1 1 calc R U . . .
C20 C 0.1705(6) 0.0529(6) 0.8807(5) 0.131(3) Uani 1 1 d . . . . .
H20A H 0.153098 0.000635 0.957211 0.157 Uiso 1 1 calc R U . . .
H20B H 0.256223 0.040777 0.861784 0.157 Uiso 1 1 calc R U . . .
C21 C 0.1207(8) 0.0269(6) 0.8084(6) 0.170(3) Uani 1 1 d . . . . .
H21A H 0.036122 0.031913 0.831920 0.203 Uiso 1 1 calc R U . . .
H21B H 0.159021 -0.051395 0.815795 0.203 Uiso 1 1 calc R U . . .
C44 C 0.6142(8) 0.8858(6) -0.1931(5) 0.155(3) Uani 1 1 d . . . . .
H44A H 0.651515 0.899920 -0.148192 0.185 Uiso 1 1 calc R U . . .
H44B H 0.528950 0.902244 -0.170506 0.185 Uiso 1 1 calc R U . . .
C27 C 0.7240(6) 0.1302(7) 0.8315(6) 0.162(3) Uani 1 1 d . . . . .
H27 H 0.793515 0.092356 0.863841 0.195 Uiso 1 1 calc R U . . .
C4 C 0.1300(8) 0.8811(6) -0.3918(6) 0.130(3) Uani 1 1 d . . . . .
H4 H 0.135545 0.929568 -0.466689 0.156 Uiso 1 1 calc R U . . .
C43 C 0.6420(8) 0.9668(6) -0.3147(6) 0.177(3) Uani 1 1 d . U . . .
H43A H 0.611872 1.046716 -0.324810 0.212 Uiso 1 1 calc R U . . .
H43B H 0.727409 0.953275 -0.336579 0.212 Uiso 1 1 calc R U . . .
C3 C 0.0221(7) 0.8725(7) -0.3314(6) 0.162(4) Uani 1 1 d . . . . .
H3A H -0.046579 0.914685 -0.364591 0.194 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
C35 C38 1.501(6) . ?
C35 C36 1.382(5) . ?
C35 C34 1.388(5) . ?
C32 C30 1.487(6) . ?
C32 C37 1.385(5) . ?
C32 C33 1.384(5) . ?
C10 C8 1.491(6) . ?
C10 C11 1.367(5) . ?
C10 C15 1.393(5) . ?
C13 C16 1.508(6) . ?
C13 C12 1.383(5) . ?
C13 C14 1.378(5) . ?
N1 H1 0.8600 . ?
N1 C16 1.330(5) . ?
N1 C17 1.468(5) . ?
C16 O1 1.219(4) . ?
C38 N3 1.340(5) . ?
C38 O2 1.228(4) . ?
C30 C29 1.347(6) . ?
C30 C31 1.447(6) . ?
N3 H3 0.8600 . ?
N3 C39 1.448(5) . ?
C8 C7 1.332(5) . ?
C8 C9 1.428(6) . ?
C36 H36 0.9300 . ?
C36 C37 1.366(5) . ?
C12 H12 0.9300 . ?
C12 C11 1.373(6) . ?
C29 H29 0.9300 . ?
C29 C23 1.450(6) . ?
C7 H7 0.9300 . ?
C7 C1 1.452(6) . ?
C11 H11 0.9300 . ?
C37 H37 0.9300 . ?
C1 C6 1.364(6) . ?
C1 C2 1.364(6) . ?
C31 N4 1.126(5) . ?
C17 H17 0.9800 . ?
C17 C18 1.497(5) . ?
C17 C22 1.482(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.385(6) . ?
C39 H39 0.9800 . ?
C39 C40 1.480(6) . ?
C39 C44 1.466(7) . ?
C15 H15 0.9300 . ?
C34 H34 0.9300 . ?
C34 C33 1.383(6) . ?
C23 C24 1.376(6) . ?
C23 C28 1.364(6) . ?
C9 N2 1.133(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.521(6) . ?
C33 H33 0.9300 . ?
C6 H6 0.9300 . ?
C6 C5 1.387(7) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.499(8) . ?
C5 H5 0.9300 . ?
C5 C4 1.340(7) . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C40 C41 1.517(7) . ?
C24 H24 0.9300 . ?
C24 C25 1.371(6) . ?
C25 H25 0.9300 . ?
C25 C26 1.356(6) . ?
C28 H28 0.9300 . ?
C28 C27 1.361(7) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C21 1.533(8) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C41 C42 1.492(8) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C42 C43 1.498(8) . ?
C2 H2 0.9300 . ?
C2 C3 1.375(8) . ?
C26 H26 0.9300 . ?
C26 C27 1.348(8) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.511(8) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C44 H44A 0.9700 . ?
C44 H44B 0.9700 . ?
C44 C43 1.534(8) . ?
C27 H27 0.9300 . ?
C4 H4 0.9300 . ?
C4 C3 1.349(9) . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C3 H3A 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
C36 C35 C38 118.0(4) . . ?
C36 C35 C34 117.9(4) . . ?
C34 C35 C38 124.0(4) . . ?
C37 C32 C30 120.7(4) . . ?
C33 C32 C30 121.3(4) . . ?
C33 C32 C37 118.0(4) . . ?
C11 C10 C8 120.9(4) . . ?
C11 C10 C15 118.6(4) . . ?
C15 C10 C8 120.4(4) . . ?
C12 C13 C16 116.9(4) . . ?
C14 C13 C16 124.3(4) . . ?
C14 C13 C12 118.8(4) . . ?
C16 N1 H1 118.7 . . ?
C16 N1 C17 122.7(4) . . ?
C17 N1 H1 118.7 . . ?
N1 C16 C13 116.2(4) . . ?
O1 C16 C13 120.5(4) . . ?
O1 C16 N1 123.4(4) . . ?
N3 C38 C35 117.9(4) . . ?
O2 C38 C35 120.3(4) . . ?
O2 C38 N3 121.8(4) . . ?
C29 C30 C32 125.3(4) . . ?
C29 C30 C31 120.2(4) . . ?
C31 C30 C32 114.4(4) . . ?
C38 N3 H3 118.2 . . ?
C38 N3 C39 123.5(4) . . ?
C39 N3 H3 118.2 . . ?
C7 C8 C10 124.5(4) . . ?
C7 C8 C9 120.4(4) . . ?
C9 C8 C10 115.0(4) . . ?
C35 C36 H36 118.9 . . ?
C37 C36 C35 122.2(4) . . ?
C37 C36 H36 118.9 . . ?
C13 C12 H12 119.9 . . ?
C11 C12 C13 120.3(4) . . ?
C11 C12 H12 119.9 . . ?
C30 C29 H29 114.2 . . ?
C30 C29 C23 131.5(4) . . ?
C23 C29 H29 114.2 . . ?
C8 C7 H7 114.5 . . ?
C8 C7 C1 131.0(4) . . ?
C1 C7 H7 114.5 . . ?
C10 C11 C12 121.5(4) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C32 C37 H37 119.8 . . ?
C36 C37 C32 120.3(4) . . ?
C36 C37 H37 119.8 . . ?
C6 C1 C7 125.2(5) . . ?
C6 C1 C2 116.0(5) . . ?
C2 C1 C7 118.7(5) . . ?
N4 C31 C30 174.8(5) . . ?
N1 C17 H17 108.3 . . ?
N1 C17 C18 111.0(4) . . ?
N1 C17 C22 109.9(4) . . ?
C18 C17 H17 108.3 . . ?
C22 C17 H17 108.3 . . ?
C22 C17 C18 111.1(4) . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C15 120.8(4) . . ?
C15 C14 H14 119.6 . . ?
N3 C39 H39 107.8 . . ?
N3 C39 C40 112.0(4) . . ?
N3 C39 C44 110.9(5) . . ?
C40 C39 H39 107.8 . . ?
C44 C39 H39 107.8 . . ?
C44 C39 C40 110.3(5) . . ?
C10 C15 H15 120.0 . . ?
C14 C15 C10 119.9(4) . . ?
C14 C15 H15 120.0 . . ?
C35 C34 H34 120.1 . . ?
C33 C34 C35 119.9(4) . . ?
C33 C34 H34 120.1 . . ?
C24 C23 C29 126.5(5) . . ?
C28 C23 C29 116.6(5) . . ?
C28 C23 C24 116.9(5) . . ?
N2 C9 C8 176.5(5) . . ?
C17 C18 H18A 109.4 . . ?
C17 C18 H18B 109.4 . . ?
C17 C18 C19 111.3(4) . . ?
H18A C18 H18B 108.0 . . ?
C19 C18 H18A 109.4 . . ?
C19 C18 H18B 109.4 . . ?
C32 C33 H33 119.1 . . ?
C34 C33 C32 121.7(4) . . ?
C34 C33 H33 119.1 . . ?
C1 C6 H6 118.7 . . ?
C1 C6 C5 122.6(5) . . ?
C5 C6 H6 118.7 . . ?
C18 C19 H19A 109.4 . . ?
C18 C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?
C20 C19 C18 111.0(5) . . ?
C20 C19 H19A 109.4 . . ?
C20 C19 H19B 109.4 . . ?
C6 C5 H5 120.5 . . ?
C4 C5 C6 119.0(6) . . ?
C4 C5 H5 120.5 . . ?
C39 C40 H40A 109.1 . . ?
C39 C40 H40B 109.1 . . ?
C39 C40 C41 112.3(5) . . ?
H40A C40 H40B 107.9 . . ?
C41 C40 H40A 109.1 . . ?
C41 C40 H40B 109.1 . . ?
C23 C24 H24 119.3 . . ?
C25 C24 C23 121.4(5) . . ?
C25 C24 H24 119.3 . . ?
C24 C25 H25 119.9 . . ?
C26 C25 C24 120.3(6) . . ?
C26 C25 H25 119.9 . . ?
C23 C28 H28 119.3 . . ?
C27 C28 C23 121.4(6) . . ?
C27 C28 H28 119.3 . . ?
C17 C22 H22A 109.5 . . ?
C17 C22 H22B 109.5 . . ?
C17 C22 C21 110.9(5) . . ?
H22A C22 H22B 108.0 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C40 C41 H41A 109.5 . . ?
C40 C41 H41B 109.5 . . ?
H41A C41 H41B 108.1 . . ?
C42 C41 C40 110.7(5) . . ?
C42 C41 H41A 109.5 . . ?
C42 C41 H41B 109.5 . . ?
C41 C42 H42A 109.8 . . ?
C41 C42 H42B 109.8 . . ?
C41 C42 C43 109.5(6) . . ?
H42A C42 H42B 108.2 . . ?
C43 C42 H42A 109.8 . . ?
C43 C42 H42B 109.8 . . ?
C1 C2 H2 118.9 . . ?
C1 C2 C3 122.2(6) . . ?
C3 C2 H2 118.9 . . ?
C25 C26 H26 120.6 . . ?
C27 C26 C25 118.8(6) . . ?
C27 C26 H26 120.6 . . ?
C19 C20 H20A 109.6 . . ?
C19 C20 H20B 109.6 . . ?
C19 C20 C21 110.5(5) . . ?
H20A C20 H20B 108.1 . . ?
C21 C20 H20A 109.6 . . ?
C21 C20 H20B 109.6 . . ?
C22 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
C20 C21 C22 110.6(6) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 108.1 . . ?
C39 C44 H44A 109.4 . . ?
C39 C44 H44B 109.4 . . ?
C39 C44 C43 111.1(6) . . ?
H44A C44 H44B 108.0 . . ?
C43 C44 H44A 109.4 . . ?
C43 C44 H44B 109.4 . . ?
C28 C27 H27 119.4 . . ?
C26 C27 C28 121.3(6) . . ?
C26 C27 H27 119.4 . . ?
C5 C4 H4 119.8 . . ?
C5 C4 C3 120.4(6) . . ?
C3 C4 H4 119.8 . . ?
C42 C43 C44 109.9(6) . . ?
C42 C43 H43A 109.7 . . ?
C42 C43 H43B 109.7 . . ?
C44 C43 H43A 109.7 . . ?
C44 C43 H43B 109.7 . . ?
H43A C43 H43B 108.2 . . ?
C2 C3 H3A 120.1 . . ?
C4 C3 C2 119.7(6) . . ?
C4 C3 H3A 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C35 C38 N3 C39 176.2(4) . . . . ?
C35 C36 C37 C32 -0.4(7) . . . . ?
C35 C34 C33 C32 0.3(7) . . . . ?
C32 C30 C29 C23 179.8(5) . . . . ?
C10 C8 C7 C1 -179.6(5) . . . . ?
C13 C12 C11 C10 -0.4(7) . . . . ?
C13 C14 C15 C10 -1.4(7) . . . . ?
N1 C17 C18 C19 -178.9(4) . . . . ?
N1 C17 C22 C21 179.8(5) . . . . ?
C16 C13 C12 C11 179.6(4) . . . . ?
C16 C13 C14 C15 -178.8(4) . . . . ?
C16 N1 C17 C18 -147.1(4) . . . . ?
C16 N1 C17 C22 89.6(6) . . . . ?
C38 C35 C36 C37 178.5(4) . . . . ?
C38 C35 C34 C33 -178.3(4) . . . . ?
C38 N3 C39 C40 144.5(5) . . . . ?
C38 N3 C39 C44 -91.8(6) . . . . ?
C30 C32 C37 C36 178.3(4) . . . . ?
C30 C32 C33 C34 -178.2(4) . . . . ?
C30 C29 C23 C24 -12.8(9) . . . . ?
C30 C29 C23 C28 168.2(6) . . . . ?
N3 C39 C40 C41 179.6(5) . . . . ?
N3 C39 C44 C43 178.7(6) . . . . ?
C8 C10 C11 C12 -177.8(4) . . . . ?
C8 C10 C15 C14 178.7(4) . . . . ?
C8 C7 C1 C6 23.6(8) . . . . ?
C8 C7 C1 C2 -158.7(5) . . . . ?
C36 C35 C38 N3 -168.7(4) . . . . ?
C36 C35 C38 O2 10.9(7) . . . . ?
C36 C35 C34 C33 -0.1(7) . . . . ?
C12 C13 C16 N1 150.8(4) . . . . ?
C12 C13 C16 O1 -28.9(7) . . . . ?
C12 C13 C14 C15 1.9(7) . . . . ?
C29 C23 C24 C25 179.5(5) . . . . ?
C29 C23 C28 C27 -178.3(6) . . . . ?
C7 C1 C6 C5 -179.7(5) . . . . ?
C7 C1 C2 C3 178.5(6) . . . . ?
C11 C10 C8 C7 30.3(7) . . . . ?
C11 C10 C8 C9 -153.4(4) . . . . ?
C11 C10 C15 C14 -0.1(7) . . . . ?
C37 C32 C30 C29 -12.3(7) . . . . ?
C37 C32 C30 C31 170.3(4) . . . . ?
C37 C32 C33 C34 -0.4(7) . . . . ?
O2 C38 N3 C39 -3.4(8) . . . . ?
C1 C6 C5 C4 -0.3(9) . . . . ?
C1 C2 C3 C4 2.3(12) . . . . ?
C31 C30 C29 C23 -2.9(8) . . . . ?
C17 N1 C16 C13 -174.8(4) . . . . ?
C17 N1 C16 O1 4.8(8) . . . . ?
C17 C18 C19 C20 56.0(6) . . . . ?
C17 C22 C21 C20 -56.8(9) . . . . ?
C14 C13 C16 N1 -28.5(7) . . . . ?
C14 C13 C16 O1 151.9(5) . . . . ?
C14 C13 C12 C11 -1.1(7) . . . . ?
C39 C40 C41 C42 -56.0(7) . . . . ?
C39 C44 C43 C42 58.8(10) . . . . ?
C15 C10 C8 C7 -148.5(4) . . . . ?
C15 C10 C8 C9 27.9(6) . . . . ?
C15 C10 C11 C12 1.0(7) . . . . ?
C34 C35 C38 N3 9.5(7) . . . . ?
C34 C35 C38 O2 -170.9(4) . . . . ?
C34 C35 C36 C37 0.2(7) . . . . ?
C23 C24 C25 C26 -0.3(8) . . . . ?
C23 C28 C27 C26 -1.8(12) . . . . ?
C9 C8 C7 C1 4.2(8) . . . . ?
C18 C17 C22 C21 56.6(7) . . . . ?
C18 C19 C20 C21 -56.0(7) . . . . ?
C33 C32 C30 C29 165.4(5) . . . . ?
C33 C32 C30 C31 -12.0(7) . . . . ?
C33 C32 C37 C36 0.5(7) . . . . ?
C6 C1 C2 C3 -3.6(9) . . . . ?
C6 C5 C4 C3 -1.2(11) . . . . ?
C19 C20 C21 C22 56.2(8) . . . . ?
C5 C4 C3 C2 0.2(12) . . . . ?
C40 C39 C44 C43 -56.6(8) . . . . ?
C40 C41 C42 C43 56.9(7) . . . . ?
C24 C23 C28 C27 2.5(10) . . . . ?
C24 C25 C26 C27 1.1(10) . . . . ?
C25 C26 C27 C28 0.0(12) . . . . ?
C28 C23 C24 C25 -1.5(8) . . . . ?
C22 C17 C18 C19 -56.3(6) . . . . ?
C41 C42 C43 C44 -58.2(9) . . . . ?
C2 C1 C6 C5 2.6(8) . . . . ?
C44 C39 C40 C41 55.5(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    Light-sensitive,Photo-sensitive
####################################################################### 
# 
# 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_exp_7610
_database_code_depnum_ccdc_archive 'CCDC 2225645'
loop_
_audit_author_name
_audit_author_address
'Pengyu Li'
;Beijing University of Chemical Technology
China
;
_audit_update_record             
;
2022-12-11 deposited with the CCDC.	2023-05-16 downloaded from the CCDC.
;
_audit_creation_date             2022-09-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C23 H24 N2 O2'
_chemical_formula_sum            'C23 H24 N2 O2'
_chemical_formula_weight         360.44
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.4245(6)
_cell_length_b                   11.8517(12)
_cell_length_c                   12.7062(10)
_cell_angle_alpha                81.945(7)
_cell_angle_beta                 82.718(7)
_cell_angle_gamma                87.297(8)
_cell_volume                     949.78(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1239
_cell_measurement_temperature    293(3)
_cell_measurement_theta_max      27.2490
_cell_measurement_theta_min      3.3960
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.956
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95259
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0676
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6268
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         3.263
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      293(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -33.00   11.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       16.2414  -57.0000   90.0000 44

#__ type_ start__ end____ width___ exp.time_
  2 omega  -10.00   83.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       16.2414   77.0000  150.0000 93

#__ type_ start__ end____ width___ exp.time_
  3 omega  -10.00   81.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       16.2414   77.0000    0.0000 91

#__ type_ start__ end____ width___ exp.time_
  4 omega  -51.00   43.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       16.2414  -77.0000 -120.0000 94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0458809000
_diffrn_orient_matrix_UB_12      -0.0535889000
_diffrn_orient_matrix_UB_13      0.0016349000
_diffrn_orient_matrix_UB_21      -0.0619168000
_diffrn_orient_matrix_UB_22      0.0081774000
_diffrn_orient_matrix_UB_23      0.0488222000
_diffrn_orient_matrix_UB_31      -0.0803781000
_diffrn_orient_matrix_UB_32      0.0267980000
_diffrn_orient_matrix_UB_33      -0.0289825000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2478
_reflns_number_total             3635
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.07
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3635
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0559
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0554P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1169
_refine_ls_wR_factor_ref         0.1407
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C21(H21A,H21B), C18(H18A,H18B), C20(H20A,H20B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C10(H10), C3(H3), C4(H4), C6(H6), C7(H7), C16(H16), C13(H13),
 C15(H15), C12(H12)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.0606(3) 0.80172(13) 0.81312(12) 0.0227(4) Uani 1 1 d . . . . .
H1 H 0.088538 0.867307 0.828569 0.027 Uiso 1 1 calc R U . . .
O1 O 0.1197(2) 0.61159(11) 0.84419(11) 0.0302(4) Uani 1 1 d . . . . .
O2 O 1.6297(2) 0.61785(12) 1.39439(11) 0.0314(4) Uani 1 1 d . . . . .
C5 C 0.6463(3) 0.74441(15) 1.05501(14) 0.0196(4) Uani 1 1 d . . . . .
C17 C -0.0920(3) 0.79606(16) 0.73873(15) 0.0238(5) Uani 1 1 d . . . . .
H17 H -0.169558 0.725859 0.762004 0.029 Uiso 1 1 calc R U . . .
C8 C 0.8124(3) 0.75327(15) 1.12438(15) 0.0194(5) Uani 1 1 d . . . . .
C10 C 0.9460(3) 0.66669(15) 1.15496(15) 0.0214(5) Uani 1 1 d . . . . .
H10 H 0.922367 0.598853 1.130022 0.026 Uiso 1 1 calc R U . . .
C11 C 1.1184(3) 0.65901(16) 1.21890(15) 0.0207(5) Uani 1 1 d . . . . .
C3 C 0.3321(3) 0.82084(15) 0.97957(15) 0.0230(5) Uani 1 1 d . . . . .
H3 H 0.230552 0.878997 0.972102 0.028 Uiso 1 1 calc R U . . .
C14 C 1.4647(3) 0.62485(16) 1.33655(15) 0.0233(5) Uani 1 1 d . . . . .
C1 C 0.1596(3) 0.70878(16) 0.85854(15) 0.0214(5) Uani 1 1 d . . . . .
C4 C 0.4889(3) 0.82967(15) 1.04287(15) 0.0231(5) Uani 1 1 d . . . . .
H4 H 0.490071 0.893334 1.078040 0.028 Uiso 1 1 calc R U . . .
C6 C 0.6397(3) 0.65105(16) 1.00001(15) 0.0231(5) Uani 1 1 d . . . . .
H6 H 0.743993 0.594054 1.004672 0.028 Uiso 1 1 calc R U . . .
C2 C 0.3243(3) 0.72646(15) 0.92709(14) 0.0195(4) Uani 1 1 d . . . . .
C22 C -0.2490(3) 0.89550(18) 0.74033(17) 0.0312(5) Uani 1 1 d . . . . .
H22A H -0.320860 0.895244 0.812268 0.037 Uiso 1 1 calc R U . . .
H22B H -0.175292 0.966369 0.720660 0.037 Uiso 1 1 calc R U . . .
C7 C 0.4806(3) 0.64235(16) 0.93893(15) 0.0231(5) Uani 1 1 d . . . . .
H7 H 0.477663 0.578245 0.904548 0.028 Uiso 1 1 calc R U . . .
C16 C 1.2327(3) 0.55573(16) 1.22897(16) 0.0245(5) Uani 1 1 d . . . . .
H16 H 1.192277 0.496513 1.195833 0.029 Uiso 1 1 calc R U . . .
C13 C 1.3513(3) 0.72810(17) 1.32955(16) 0.0293(5) Uani 1 1 d . . . . .
H13 H 1.390580 0.786448 1.364145 0.035 Uiso 1 1 calc R U . . .
C9 C 0.8230(3) 0.86233(17) 1.15932(16) 0.0279(5) Uani 1 1 d . . . . .
C15 C 1.4034(3) 0.53774(16) 1.28614(16) 0.0251(5) Uani 1 1 d . . . . .
H15 H 1.476253 0.467889 1.290695 0.030 Uiso 1 1 calc R U . . .
C12 C 1.1826(3) 0.74507(16) 1.27241(16) 0.0263(5) Uani 1 1 d . . . . .
H12 H 1.109199 0.814776 1.268987 0.032 Uiso 1 1 calc R U . . .
C23 C 1.7476(3) 0.51191(18) 1.40389(17) 0.0342(6) Uani 1 1 d . . . . .
H23A H 1.799249 0.493796 1.333792 0.051 Uiso 1 1 calc R U . . .
H23B H 1.658648 0.452513 1.441123 0.051 Uiso 1 1 calc R U . . .
H23C H 1.863663 0.518464 1.443125 0.051 Uiso 1 1 calc R U . . .
N2 N 0.8267(3) 0.95054(15) 1.18570(16) 0.0448(6) Uani 1 1 d . . . . .
C21 C -0.4087(4) 0.88898(19) 0.66352(18) 0.0362(6) Uani 1 1 d . . . . .
H21A H -0.501582 0.955948 0.663227 0.043 Uiso 1 1 calc R U . . .
H21B H -0.493144 0.822490 0.688078 0.043 Uiso 1 1 calc R U . . .
C18 C 0.0149(4) 0.7904(2) 0.62529(17) 0.0359(6) Uani 1 1 d . . . . .
H18A H 0.096452 0.858026 0.601107 0.043 Uiso 1 1 calc R U . . .
H18B H 0.110203 0.724485 0.625247 0.043 Uiso 1 1 calc R U . . .
C20 C -0.3048(4) 0.8817(2) 0.55033(18) 0.0427(6) Uani 1 1 d . . . . .
H20A H -0.234429 0.952210 0.522213 0.051 Uiso 1 1 calc R U . . .
H20B H -0.411020 0.871971 0.504764 0.051 Uiso 1 1 calc R U . . .
C19 C -0.1462(4) 0.7823(2) 0.54871(18) 0.0494(7) Uani 1 1 d . . . . .
H19A H -0.074953 0.782299 0.476670 0.059 Uiso 1 1 calc R U . . .
H19B H -0.218893 0.711191 0.569057 0.059 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 H1 0.8600 . ?
N1 C17 1.456(2) . ?
N1 C1 1.341(2) . ?
O1 C1 1.235(2) . ?
O2 C14 1.358(2) . ?
O2 C23 1.434(2) . ?
C5 C8 1.484(3) . ?
C5 C4 1.402(2) . ?
C5 C6 1.394(2) . ?
C17 H17 0.9800 . ?
C17 C22 1.515(2) . ?
C17 C18 1.525(3) . ?
C8 C10 1.353(2) . ?
C8 C9 1.432(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.447(3) . ?
C11 C16 1.396(2) . ?
C11 C12 1.406(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.383(3) . ?
C3 C2 1.386(2) . ?
C14 C13 1.392(2) . ?
C14 C15 1.385(3) . ?
C1 C2 1.493(3) . ?
C4 H4 0.9300 . ?
C6 H6 0.9300 . ?
C6 C7 1.375(3) . ?
C2 C7 1.388(2) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C21 1.515(3) . ?
C7 H7 0.9300 . ?
C16 H16 0.9300 . ?
C16 C15 1.383(3) . ?
C13 H13 0.9300 . ?
C13 C12 1.372(3) . ?
C9 N2 1.144(2) . ?
C15 H15 0.9300 . ?
C12 H12 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C20 1.519(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.522(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C19 1.522(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 N1 H1 118.7 . . ?
C1 N1 H1 118.7 . . ?
C1 N1 C17 122.65(16) . . ?
C14 O2 C23 117.07(15) . . ?
C4 C5 C8 121.09(15) . . ?
C6 C5 C8 121.44(16) . . ?
C6 C5 C4 117.47(18) . . ?
N1 C17 H17 107.8 . . ?
N1 C17 C22 111.31(14) . . ?
N1 C17 C18 111.49(17) . . ?
C22 C17 H17 107.8 . . ?
C22 C17 C18 110.56(16) . . ?
C18 C17 H17 107.8 . . ?
C10 C8 C5 124.28(16) . . ?
C10 C8 C9 120.69(18) . . ?
C9 C8 C5 115.03(15) . . ?
C8 C10 H10 113.7 . . ?
C8 C10 C11 132.54(18) . . ?
C11 C10 H10 113.7 . . ?
C16 C11 C10 116.90(16) . . ?
C16 C11 C12 116.50(18) . . ?
C12 C11 C10 126.59(16) . . ?
C4 C3 H3 119.6 . . ?
C4 C3 C2 120.88(17) . . ?
C2 C3 H3 119.6 . . ?
O2 C14 C13 115.98(17) . . ?
O2 C14 C15 124.84(17) . . ?
C15 C14 C13 119.18(18) . . ?
N1 C1 C2 117.54(16) . . ?
O1 C1 N1 122.13(18) . . ?
O1 C1 C2 120.32(16) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 C5 121.21(16) . . ?
C3 C4 H4 119.4 . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.68(16) . . ?
C7 C6 H6 119.7 . . ?
C3 C2 C1 124.64(16) . . ?
C3 C2 C7 117.80(18) . . ?
C7 C2 C1 117.56(15) . . ?
C17 C22 H22A 109.4 . . ?
C17 C22 H22B 109.4 . . ?
H22A C22 H22B 108.0 . . ?
C21 C22 C17 111.23(16) . . ?
C21 C22 H22A 109.4 . . ?
C21 C22 H22B 109.4 . . ?
C6 C7 C2 121.92(16) . . ?
C6 C7 H7 119.0 . . ?
C2 C7 H7 119.0 . . ?
C11 C16 H16 118.6 . . ?
C15 C16 C11 122.78(18) . . ?
C15 C16 H16 118.6 . . ?
C14 C13 H13 119.5 . . ?
C12 C13 C14 120.99(19) . . ?
C12 C13 H13 119.5 . . ?
N2 C9 C8 178.0(2) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 C14 119.31(17) . . ?
C16 C15 H15 120.3 . . ?
C11 C12 H12 119.4 . . ?
C13 C12 C11 121.21(17) . . ?
C13 C12 H12 119.4 . . ?
O2 C23 H23A 109.5 . . ?
O2 C23 H23B 109.5 . . ?
O2 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C21 H21A 109.2 . . ?
C22 C21 H21B 109.2 . . ?
C22 C21 C20 111.91(19) . . ?
H21A C21 H21B 107.9 . . ?
C20 C21 H21A 109.2 . . ?
C20 C21 H21B 109.2 . . ?
C17 C18 H18A 109.4 . . ?
C17 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
C19 C18 C17 110.99(18) . . ?
C19 C18 H18A 109.4 . . ?
C19 C18 H18B 109.4 . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
C21 C20 C19 110.79(18) . . ?
H20A C20 H20B 108.1 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C18 C19 H19A 109.4 . . ?
C18 C19 H19B 109.4 . . ?
C20 C19 C18 110.99(17) . . ?
C20 C19 H19A 109.4 . . ?
C20 C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C17 C22 C21 -179.57(18) . . . . ?
N1 C17 C18 C19 178.94(17) . . . . ?
N1 C1 C2 C3 25.1(3) . . . . ?
N1 C1 C2 C7 -154.83(18) . . . . ?
O1 C1 C2 C3 -155.63(19) . . . . ?
O1 C1 C2 C7 24.4(3) . . . . ?
O2 C14 C13 C12 179.4(2) . . . . ?
O2 C14 C15 C16 -179.65(19) . . . . ?
C5 C8 C10 C11 178.3(2) . . . . ?
C5 C6 C7 C2 1.7(3) . . . . ?
C17 N1 C1 O1 -3.7(3) . . . . ?
C17 N1 C1 C2 175.57(17) . . . . ?
C17 C22 C21 C20 -55.5(3) . . . . ?
C17 C18 C19 C20 56.6(3) . . . . ?
C8 C5 C4 C3 -179.03(18) . . . . ?
C8 C5 C6 C7 177.81(18) . . . . ?
C8 C10 C11 C16 -176.10(19) . . . . ?
C8 C10 C11 C12 4.1(4) . . . . ?
C10 C11 C16 C15 178.80(19) . . . . ?
C10 C11 C12 C13 -179.0(2) . . . . ?
C11 C16 C15 C14 0.4(3) . . . . ?
C3 C2 C7 C6 -0.3(3) . . . . ?
C14 C13 C12 C11 -0.1(3) . . . . ?
C1 N1 C17 C22 153.07(18) . . . . ?
C1 N1 C17 C18 -83.0(2) . . . . ?
C1 C2 C7 C6 179.70(19) . . . . ?
C4 C5 C8 C10 167.83(19) . . . . ?
C4 C5 C8 C9 -11.6(3) . . . . ?
C4 C5 C6 C7 -1.8(3) . . . . ?
C4 C3 C2 C1 179.07(18) . . . . ?
C4 C3 C2 C7 -1.0(3) . . . . ?
C6 C5 C8 C10 -11.8(3) . . . . ?
C6 C5 C8 C9 168.74(18) . . . . ?
C6 C5 C4 C3 0.6(3) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
C22 C17 C18 C19 -56.7(2) . . . . ?
C22 C21 C20 C19 54.9(3) . . . . ?
C16 C11 C12 C13 1.2(3) . . . . ?
C13 C14 C15 C16 0.8(3) . . . . ?
C9 C8 C10 C11 -2.3(3) . . . . ?
C15 C14 C13 C12 -0.9(3) . . . . ?
C12 C11 C16 C15 -1.4(3) . . . . ?
C23 O2 C14 C13 179.28(17) . . . . ?
C23 O2 C14 C15 -0.3(3) . . . . ?
C21 C20 C19 C18 -55.3(3) . . . . ?
C18 C17 C22 C21 55.9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_preparation       Luminescent
