# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_11661
_audit_block_doi                 10.5517/ccdc.csd.cc2ch1zx
_database_code_depnum_ccdc_archive 'CCDC 2189219'
loop_
_audit_author_name
_audit_author_address
'zeng guohui'
;South China University of Technology
China
;
_audit_update_record             
;
2022-07-11 deposited with the CCDC.	2024-04-03 downloaded from the CCDC.
;
_audit_creation_date             2022-07-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H32 N2 O2'
_chemical_formula_sum            'C23 H32 N2 O2'
_chemical_formula_weight         368.50
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.8978(19)
_cell_length_b                   9.9999(9)
_cell_length_c                   14.9001(18)
_cell_angle_alpha                90
_cell_angle_beta                 93.852(13)
_cell_angle_gamma                90
_cell_volume                     2066.1(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1535
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.3180
_cell_measurement_theta_min      2.8200
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82904
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0529
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7792
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.499
_diffrn_reflns_theta_max         24.499
_diffrn_reflns_theta_min         2.075
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -50.00 -23.00   0.90    4.50    --   15.65 -57.00 -30.00   30
  2  ω    -17.00  10.00   0.90    4.50    --  -16.59 -99.00   0.00   30
  3  ω    -72.00  41.40   0.90    4.50    --  -16.59   0.00 -60.00  126
  4  ω      1.00  81.10   0.90    4.50    --   15.65  38.00 150.00   89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0464979000
_diffrn_orient_matrix_UB_12      0.0286225000
_diffrn_orient_matrix_UB_13      0.0079282000
_diffrn_orient_matrix_UB_21      -0.0039549000
_diffrn_orient_matrix_UB_22      0.0291357000
_diffrn_orient_matrix_UB_23      -0.0434510000
_diffrn_orient_matrix_UB_31      -0.0209336000
_diffrn_orient_matrix_UB_32      0.0580800000
_diffrn_orient_matrix_UB_33      0.0179346000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2302
_reflns_number_total             3424
_reflns_odcompleteness_completeness 99.47
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3424
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1093
_refine_ls_R_factor_gt           0.0669
_refine_ls_restrained_S_all      1.087
_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)+(0.0387P)²+0.9511P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1217
_refine_ls_wR_factor_ref         0.1404
_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
2. Rigid bond restraints
 C7, N2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3.a Ternary CH refined with riding coordinates:
 C1(H1)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C16(H16A,H16B)
3.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C9(H9), C14(H14), C15(H15), C13(H13), C12(H12), C11(H11), C10(H10)
3.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C23(H23A,H23B,H23C), C19(H19A,H19B,H19C), C22(H22A,H22B,
 H22C), C21(H21A,H21B,H21C)
;
_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
O2 O 0.48314(14) 0.1947(2) 0.54305(13) 0.0572(6) Uani 1 1 d . . . . .
N1 N 0.72613(14) 0.3391(2) 0.63371(14) 0.0397(6) Uani 1 1 d . . . . .
O1 O 0.71174(14) 0.56830(19) 0.62589(16) 0.0664(7) Uani 1 1 d . . . . .
N2 N 0.34755(16) 0.6346(2) 0.67757(15) 0.0468(6) Uani 1 1 d . U . . .
C8 C 0.34748(17) 0.6651(3) 0.76866(19) 0.0412(7) Uani 1 1 d . . . . .
C2 C 0.56580(18) 0.2870(2) 0.67113(18) 0.0375(6) Uani 1 1 d . . . . .
C1 C 0.56992(18) 0.4254(2) 0.62549(18) 0.0381(7) Uani 1 1 d . . . . .
H1 H 0.5482 0.4130 0.5621 0.046 Uiso 1 1 calc R U . . .
C20 C 0.83338(19) 0.3259(3) 0.63666(19) 0.0439(7) Uani 1 1 d . . . . .
C4 C 0.67754(19) 0.4560(3) 0.62857(18) 0.0412(7) Uani 1 1 d . . . . .
C18 C 0.48257(19) 0.2017(3) 0.63488(19) 0.0424(7) Uani 1 1 d . . . . .
C17 C 0.4187(2) 0.1451(3) 0.6844(2) 0.0488(8) Uani 1 1 d . . . . .
H17 H 0.3693 0.0950 0.6557 0.059 Uiso 1 1 calc R U . . .
C3 C 0.66398(19) 0.2254(3) 0.6493(2) 0.0447(7) Uani 1 1 d . . . . .
H3A H 0.6906 0.1720 0.6993 0.054 Uiso 1 1 calc R U . . .
H3B H 0.6565 0.1693 0.5962 0.054 Uiso 1 1 calc R U . . .
C5 C 0.51120(18) 0.5391(3) 0.66077(19) 0.0424(7) Uani 1 1 d . . . . .
H5A H 0.5277 0.6207 0.6302 0.051 Uiso 1 1 calc R U . . .
H5B H 0.5294 0.5509 0.7243 0.051 Uiso 1 1 calc R U . . .
C6 C 0.40241(18) 0.5195(3) 0.64914(19) 0.0459(7) Uani 1 1 d . . . . .
H6A H 0.3844 0.5013 0.5863 0.055 Uiso 1 1 calc R U . . .
H6B H 0.3850 0.4420 0.6836 0.055 Uiso 1 1 calc R U . . .
C9 C 0.3234(2) 0.7930(3) 0.7977(2) 0.0515(8) Uani 1 1 d . . . . .
H9 H 0.3098 0.8597 0.7553 0.062 Uiso 1 1 calc R U . . .
C14 C 0.5654(2) 0.3006(3) 0.77196(19) 0.0502(8) Uani 1 1 d . . . . .
H14 H 0.6129 0.3532 0.8013 0.060 Uiso 1 1 calc R U . . .
C15 C 0.5021(2) 0.2427(3) 0.8209(2) 0.0538(8) Uani 1 1 d . . . . .
H15 H 0.5081 0.2563 0.8827 0.065 Uiso 1 1 calc R U . . .
C13 C 0.3689(2) 0.5694(3) 0.8349(2) 0.0570(8) Uani 1 1 d . . . . .
H13 H 0.3858 0.4832 0.8187 0.068 Uiso 1 1 calc R U . . .
C16 C 0.4225(2) 0.1578(3) 0.7843(2) 0.0642(9) Uani 1 1 d . . . . .
H16A H 0.3620 0.1950 0.8016 0.077 Uiso 1 1 calc R U . . .
H16B H 0.4293 0.0694 0.8108 0.077 Uiso 1 1 calc R U . . .
C12 C 0.3652(2) 0.6025(4) 0.9256(2) 0.0708(10) Uani 1 1 d . . . . .
H12 H 0.3799 0.5379 0.9693 0.085 Uiso 1 1 calc R U . . .
C11 C 0.3401(2) 0.7290(4) 0.9513(2) 0.0724(10) Uani 1 1 d . . . . .
H11 H 0.3373 0.7500 1.0119 0.087 Uiso 1 1 calc R U . . .
C10 C 0.3193(2) 0.8225(4) 0.8871(2) 0.0673(10) Uani 1 1 d . . . . .
H10 H 0.3020 0.9083 0.9041 0.081 Uiso 1 1 calc R U . . .
C7 C 0.3414(2) 0.7445(3) 0.6141(2) 0.0690(10) Uani 1 1 d . U . . .
H7A H 0.2817 0.7912 0.6189 0.103 Uiso 1 1 calc R U . . .
H7B H 0.3444 0.7103 0.5541 0.103 Uiso 1 1 calc R U . . .
H7C H 0.3943 0.8048 0.6272 0.103 Uiso 1 1 calc R U . . .
C23 C 0.8581(2) 0.1816(3) 0.6152(2) 0.0696(10) Uani 1 1 d . . . . .
H23A H 0.8349 0.1237 0.6603 0.104 Uiso 1 1 calc R U . . .
H23B H 0.9268 0.1723 0.6141 0.104 Uiso 1 1 calc R U . . .
H23C H 0.8282 0.1578 0.5574 0.104 Uiso 1 1 calc R U . . .
C19 C 0.4058(2) 0.1263(4) 0.4956(2) 0.0722(10) Uani 1 1 d . . . . .
H19A H 0.4169 0.1236 0.4328 0.108 Uiso 1 1 calc R U . . .
H19B H 0.3465 0.1723 0.5039 0.108 Uiso 1 1 calc R U . . .
H19C H 0.4019 0.0367 0.5183 0.108 Uiso 1 1 calc R U . . .
C22 C 0.8743(2) 0.3607(3) 0.7302(2) 0.0689(10) Uani 1 1 d . . . . .
H22A H 0.8599 0.4524 0.7431 0.103 Uiso 1 1 calc R U . . .
H22B H 0.9429 0.3481 0.7339 0.103 Uiso 1 1 calc R U . . .
H22C H 0.8461 0.3038 0.7732 0.103 Uiso 1 1 calc R U . . .
C21 C 0.8750(2) 0.4150(4) 0.5665(3) 0.0807(12) Uani 1 1 d . . . . .
H21A H 0.8455 0.3935 0.5081 0.121 Uiso 1 1 calc R U . . .
H21B H 0.9433 0.4010 0.5668 0.121 Uiso 1 1 calc R U . . .
H21C H 0.8623 0.5070 0.5801 0.121 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
O2 C18 1.371(3) . ?
O2 C19 1.421(3) . ?
N1 C20 1.494(3) . ?
N1 C4 1.350(3) . ?
N1 C3 1.455(3) . ?
O1 C4 1.221(3) . ?
N2 C8 1.391(3) . ?
N2 C6 1.459(3) . ?
N2 C7 1.449(4) . ?
C8 C9 1.398(4) . ?
C8 C13 1.393(4) . ?
C2 C1 1.545(3) . ?
C2 C18 1.508(4) . ?
C2 C3 1.551(3) . ?
C2 C14 1.509(4) . ?
C1 H1 0.9800 . ?
C1 C4 1.524(4) . ?
C1 C5 1.514(3) . ?
C20 C23 1.522(4) . ?
C20 C22 1.511(4) . ?
C20 C21 1.518(4) . ?
C18 C17 1.319(4) . ?
C17 H17 0.9300 . ?
C17 C16 1.492(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.523(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C9 H9 0.9300 . ?
C9 C10 1.369(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.314(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.470(4) . ?
C13 H13 0.9300 . ?
C13 C12 1.395(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C12 H12 0.9300 . ?
C12 C11 1.373(5) . ?
C11 H11 0.9300 . ?
C11 C10 1.355(5) . ?
C10 H10 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C18 O2 C19 117.8(2) . . ?
C4 N1 C20 124.9(2) . . ?
C4 N1 C3 112.7(2) . . ?
C3 N1 C20 121.9(2) . . ?
C8 N2 C6 119.4(2) . . ?
C8 N2 C7 117.8(2) . . ?
C7 N2 C6 114.7(2) . . ?
N2 C8 C9 121.3(3) . . ?
N2 C8 C13 121.8(3) . . ?
C13 C8 C9 116.9(3) . . ?
C1 C2 C3 101.77(19) . . ?
C18 C2 C1 113.5(2) . . ?
C18 C2 C3 111.4(2) . . ?
C18 C2 C14 110.7(2) . . ?
C14 C2 C1 111.1(2) . . ?
C14 C2 C3 107.9(2) . . ?
C2 C1 H1 107.0 . . ?
C4 C1 C2 103.4(2) . . ?
C4 C1 H1 107.0 . . ?
C5 C1 C2 118.9(2) . . ?
C5 C1 H1 107.0 . . ?
C5 C1 C4 112.9(2) . . ?
N1 C20 C23 108.4(2) . . ?
N1 C20 C22 108.7(2) . . ?
N1 C20 C21 110.7(2) . . ?
C22 C20 C23 109.7(3) . . ?
C22 C20 C21 111.3(3) . . ?
C21 C20 C23 108.1(3) . . ?
N1 C4 C1 108.3(2) . . ?
O1 C4 N1 127.2(2) . . ?
O1 C4 C1 124.5(2) . . ?
O2 C18 C2 109.3(2) . . ?
C17 C18 O2 125.8(3) . . ?
C17 C18 C2 124.8(3) . . ?
C18 C17 H17 118.6 . . ?
C18 C17 C16 122.8(3) . . ?
C16 C17 H17 118.6 . . ?
N1 C3 C2 105.3(2) . . ?
N1 C3 H3A 110.7 . . ?
N1 C3 H3B 110.7 . . ?
C2 C3 H3A 110.7 . . ?
C2 C3 H3B 110.7 . . ?
H3A C3 H3B 108.8 . . ?
C1 C5 H5A 108.6 . . ?
C1 C5 H5B 108.6 . . ?
C1 C5 C6 114.7(2) . . ?
H5A C5 H5B 107.6 . . ?
C6 C5 H5A 108.6 . . ?
C6 C5 H5B 108.6 . . ?
N2 C6 C5 113.6(2) . . ?
N2 C6 H6A 108.9 . . ?
N2 C6 H6B 108.9 . . ?
C5 C6 H6A 108.9 . . ?
C5 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C8 C9 H9 119.1 . . ?
C10 C9 C8 121.7(3) . . ?
C10 C9 H9 119.1 . . ?
C2 C14 H14 118.0 . . ?
C15 C14 C2 124.1(3) . . ?
C15 C14 H14 118.0 . . ?
C14 C15 H15 117.8 . . ?
C14 C15 C16 124.4(3) . . ?
C16 C15 H15 117.8 . . ?
C8 C13 H13 119.9 . . ?
C8 C13 C12 120.2(3) . . ?
C12 C13 H13 119.9 . . ?
C17 C16 H16A 108.9 . . ?
C17 C16 H16B 108.9 . . ?
C15 C16 C17 113.2(2) . . ?
C15 C16 H16A 108.9 . . ?
C15 C16 H16B 108.9 . . ?
H16A C16 H16B 107.8 . . ?
C13 C12 H12 119.5 . . ?
C11 C12 C13 121.0(3) . . ?
C11 C12 H12 119.5 . . ?
C12 C11 H11 120.5 . . ?
C10 C11 C12 119.0(3) . . ?
C10 C11 H11 120.5 . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.1(3) . . ?
C11 C10 H10 119.5 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
O2 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C18 C17 C16 -179.7(3) . . . . ?
N2 C8 C9 C10 177.3(3) . . . . ?
N2 C8 C13 C12 -178.0(3) . . . . ?
C8 N2 C6 C5 -70.2(3) . . . . ?
C8 C9 C10 C11 1.0(5) . . . . ?
C8 C13 C12 C11 0.3(5) . . . . ?
C2 C1 C4 N1 24.5(3) . . . . ?
C2 C1 C4 O1 -156.2(3) . . . . ?
C2 C1 C5 C6 -65.3(3) . . . . ?
C2 C18 C17 C16 -0.8(4) . . . . ?
C2 C14 C15 C16 -0.6(5) . . . . ?
C1 C2 C18 O2 52.4(3) . . . . ?
C1 C2 C18 C17 -126.6(3) . . . . ?
C1 C2 C3 N1 23.9(3) . . . . ?
C1 C2 C14 C15 128.7(3) . . . . ?
C1 C5 C6 N2 -175.7(2) . . . . ?
C20 N1 C4 O1 -0.3(5) . . . . ?
C20 N1 C4 C1 179.0(2) . . . . ?
C20 N1 C3 C2 162.1(2) . . . . ?
C4 N1 C20 C23 -163.8(3) . . . . ?
C4 N1 C20 C22 77.0(3) . . . . ?
C4 N1 C20 C21 -45.5(4) . . . . ?
C4 N1 C3 C2 -9.8(3) . . . . ?
C4 C1 C5 C6 173.4(2) . . . . ?
C18 C2 C1 C4 -148.4(2) . . . . ?
C18 C2 C1 C5 85.5(3) . . . . ?
C18 C2 C3 N1 145.2(2) . . . . ?
C18 C2 C14 C15 1.6(4) . . . . ?
C18 C17 C16 C15 1.8(4) . . . . ?
C3 N1 C20 C23 25.3(3) . . . . ?
C3 N1 C20 C22 -93.9(3) . . . . ?
C3 N1 C20 C21 143.6(3) . . . . ?
C3 N1 C4 O1 171.3(3) . . . . ?
C3 N1 C4 C1 -9.3(3) . . . . ?
C3 C2 C1 C4 -28.5(3) . . . . ?
C3 C2 C1 C5 -154.6(2) . . . . ?
C3 C2 C18 O2 -61.8(3) . . . . ?
C3 C2 C18 C17 119.2(3) . . . . ?
C3 C2 C14 C15 -120.6(3) . . . . ?
C5 C1 C4 N1 154.3(2) . . . . ?
C5 C1 C4 O1 -26.4(4) . . . . ?
C6 N2 C8 C9 159.5(2) . . . . ?
C6 N2 C8 C13 -22.2(4) . . . . ?
C9 C8 C13 C12 0.5(4) . . . . ?
C14 C2 C1 C4 86.1(2) . . . . ?
C14 C2 C1 C5 -40.0(3) . . . . ?
C14 C2 C18 O2 178.1(2) . . . . ?
C14 C2 C18 C17 -0.9(4) . . . . ?
C14 C2 C3 N1 -93.1(3) . . . . ?
C14 C15 C16 C17 -1.1(4) . . . . ?
C13 C8 C9 C10 -1.1(4) . . . . ?
C13 C12 C11 C10 -0.4(5) . . . . ?
C12 C11 C10 C9 -0.2(5) . . . . ?
C7 N2 C8 C9 12.4(4) . . . . ?
C7 N2 C8 C13 -169.2(3) . . . . ?
C7 N2 C6 C5 77.8(3) . . . . ?
C19 O2 C18 C2 -175.6(2) . . . . ?
C19 O2 C18 C17 3.4(4) . . . . ?


_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 1.252
_oxdiff_exptl_absorpt_empirical_full_min 0.854
####################################################################### 
# 
# 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_10391
_audit_block_doi                 10.5517/ccdc.csd.cc2c8f14
_database_code_depnum_ccdc_archive 'CCDC 2182835'
loop_
_audit_author_name
_audit_author_address
'guohui zeng'
;South China University of Technology
China
;
_audit_update_record             
;
2022-06-29 deposited with the CCDC.	2024-04-03 downloaded from the CCDC.
;
_audit_creation_date             2021-11-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H32 N2 O2'
_chemical_formula_sum            'C24 H32 N2 O2'
_chemical_formula_weight         380.51
_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      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                   13.2226(17)
_cell_length_b                   13.177(2)
_cell_length_c                   12.2423(16)
_cell_angle_alpha                90
_cell_angle_beta                 91.432(11)
_cell_angle_gamma                90
_cell_volume                     2132.3(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1141
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.0130
_cell_measurement_theta_min      2.7070
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_unetI/netI     0.0973
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10492
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_min         2.182
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -31.00  31.00   1.00   10.00    --  -16.28  38.00 -60.00   62
  2  ω     -4.00  44.00   1.00   10.00    --  -16.28  57.00   0.00   48
  3  ω    -25.00  23.00   1.00   10.00    --  -16.28 -99.00 -60.00   48
  4  ω    -74.00   2.00   1.00   10.00    --  -16.28 -77.00-180.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0488170000
_diffrn_orient_matrix_UB_12      0.0204826000
_diffrn_orient_matrix_UB_13      -0.0111331000
_diffrn_orient_matrix_UB_21      0.0205135000
_diffrn_orient_matrix_UB_22      0.0496516000
_diffrn_orient_matrix_UB_23      0.0019966000
_diffrn_orient_matrix_UB_31      0.0089098000
_diffrn_orient_matrix_UB_32      -0.0022095000
_diffrn_orient_matrix_UB_33      -0.0568835000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2255
_reflns_number_total             4595
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4595
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1705
_refine_ls_R_factor_gt           0.0774
_refine_ls_restrained_S_all      1.041
_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)+(0.0437P)²+0.1300P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1225
_refine_ls_wR_factor_ref         0.1572
_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
2.a Ternary CH refined with riding coordinates:
 C1(H1), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C2(H2A,H2B), C6(H6A,H6B), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C7(H7), C19(H19), C15(H15), C5(H5), C18(H18), C16(H16), C17(H17)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C)
;
_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
O2 O 0.44094(15) 0.63310(16) 0.82166(15) 0.0624(6) Uani 1 1 d . . . . .
N1 N 0.45978(15) 0.74051(17) 0.67489(16) 0.0384(6) Uani 1 1 d . . . . .
N2 N 0.08166(17) 0.48643(17) 0.75129(17) 0.0439(6) Uani 1 1 d . . . . .
O1 O 0.18385(16) 0.85904(18) 0.59262(18) 0.0692(7) Uani 1 1 d . . . . .
C14 C 0.09859(19) 0.3936(2) 0.7015(2) 0.0392(7) Uani 1 1 d . . . . .
C1 C 0.3922(2) 0.7920(2) 0.5956(2) 0.0402(7) Uani 1 1 d . . . . .
H1 H 0.4257 0.7997 0.5255 0.048 Uiso 1 1 calc R U . . .
C11 C 0.4069(2) 0.6798(2) 0.7425(2) 0.0405(7) Uani 1 1 d . . . . .
C10 C 0.29639(19) 0.6779(2) 0.70438(19) 0.0358(7) Uani 1 1 d . . . . .
H10 H 0.2607 0.7296 0.7463 0.043 Uiso 1 1 calc R U . . .
C9 C 0.30193(19) 0.7170(2) 0.58369(19) 0.0370(7) Uani 1 1 d . . . . .
C12 C 0.24648(19) 0.5764(2) 0.7269(2) 0.0416(7) Uani 1 1 d . . . . .
H12A H 0.2626 0.5565 0.8017 0.050 Uiso 1 1 calc R U . . .
H12B H 0.2748 0.5256 0.6792 0.050 Uiso 1 1 calc R U . . .
C13 C 0.13183(19) 0.5772(2) 0.7104(2) 0.0434(7) Uani 1 1 d . . . . .
H13A H 0.1048 0.6362 0.7469 0.052 Uiso 1 1 calc R U . . .
H13B H 0.1159 0.5840 0.6329 0.052 Uiso 1 1 calc R U . . .
C4 C 0.2072(2) 0.7685(2) 0.5419(2) 0.0481(8) Uani 1 1 d . . . . .
C8 C 0.3278(2) 0.6309(2) 0.5080(2) 0.0482(8) Uani 1 1 d . . . . .
H8 H 0.3928 0.6041 0.5127 0.058 Uiso 1 1 calc R U . . .
C7 C 0.2626(2) 0.5908(2) 0.4344(2) 0.0503(8) Uani 1 1 d . . . . .
H7 H 0.2821 0.5330 0.3967 0.060 Uiso 1 1 calc R U . . .
C19 C 0.0823(2) 0.3017(2) 0.7555(2) 0.0470(8) Uani 1 1 d . . . . .
H19 H 0.0592 0.3024 0.8266 0.056 Uiso 1 1 calc R U . . .
C15 C 0.1321(2) 0.3876(2) 0.5940(2) 0.0544(8) Uani 1 1 d . . . . .
H15 H 0.1437 0.4471 0.5553 0.065 Uiso 1 1 calc R U . . .
C5 C 0.1446(2) 0.7307(3) 0.4665(2) 0.0569(9) Uani 1 1 d . . . . .
H5 H 0.0864 0.7670 0.4478 0.068 Uiso 1 1 calc R U . . .
C21 C 0.5696(2) 0.7640(2) 0.6928(2) 0.0550(8) Uani 1 1 d . . . . .
C18 C 0.1001(2) 0.2102(2) 0.7049(3) 0.0627(9) Uani 1 1 d . . . . .
H18 H 0.0897 0.1501 0.7428 0.075 Uiso 1 1 calc R U . . .
C20 C 0.0612(2) 0.4869(2) 0.8674(2) 0.0598(9) Uani 1 1 d . . . . .
H20A H 0.0006 0.4490 0.8801 0.090 Uiso 1 1 calc R U . . .
H20B H 0.0526 0.5555 0.8917 0.090 Uiso 1 1 calc R U . . .
H20C H 0.1170 0.4564 0.9070 0.090 Uiso 1 1 calc R U . . .
C2 C 0.3596(2) 0.8955(2) 0.6387(3) 0.0603(9) Uani 1 1 d . . . . .
H2A H 0.3503 0.8909 0.7169 0.072 Uiso 1 1 calc R U . . .
H2B H 0.4128 0.9445 0.6262 0.072 Uiso 1 1 calc R U . . .
C6 C 0.1629(2) 0.6331(3) 0.4107(2) 0.0625(9) Uani 1 1 d . . . . .
H6A H 0.1121 0.5846 0.4325 0.075 Uiso 1 1 calc R U . . .
H6B H 0.1551 0.6431 0.3325 0.075 Uiso 1 1 calc R U . . .
C16 C 0.1483(2) 0.2959(3) 0.5448(3) 0.0678(10) Uani 1 1 d . . . . .
H16 H 0.1701 0.2941 0.4732 0.081 Uiso 1 1 calc R U . . .
C17 C 0.1328(2) 0.2067(3) 0.5996(3) 0.0711(10) Uani 1 1 d . . . . .
H17 H 0.1444 0.1447 0.5657 0.085 Uiso 1 1 calc R U . . .
C3 C 0.2642(3) 0.9315(3) 0.5851(3) 0.0789(11) Uani 1 1 d . . . . .
H3A H 0.2437 0.9945 0.6191 0.095 Uiso 1 1 calc R U . . .
H3B H 0.2763 0.9454 0.5087 0.095 Uiso 1 1 calc R U . . .
C22 C 0.6077(2) 0.8323(3) 0.6025(3) 0.0777(11) Uani 1 1 d . . . . .
H22A H 0.5961 0.8001 0.5330 0.117 Uiso 1 1 calc R U . . .
H22B H 0.6789 0.8441 0.6137 0.117 Uiso 1 1 calc R U . . .
H22C H 0.5723 0.8959 0.6038 0.117 Uiso 1 1 calc R U . . .
C23 C 0.5835(3) 0.8198(3) 0.8017(3) 0.0941(13) Uani 1 1 d . . . . .
H23A H 0.5471 0.8828 0.7988 0.141 Uiso 1 1 calc R U . . .
H23B H 0.6541 0.8330 0.8153 0.141 Uiso 1 1 calc R U . . .
H23C H 0.5581 0.7785 0.8595 0.141 Uiso 1 1 calc R U . . .
C24 C 0.6279(2) 0.6648(3) 0.6916(4) 0.1139(16) Uani 1 1 d . . . . .
H24A H 0.6071 0.6230 0.7512 0.171 Uiso 1 1 calc R U . . .
H24B H 0.6990 0.6786 0.6992 0.171 Uiso 1 1 calc R U . . .
H24C H 0.6143 0.6302 0.6238 0.171 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
O2 C11 1.225(3) . ?
N1 C1 1.468(3) . ?
N1 C11 1.357(3) . ?
N1 C21 1.495(3) . ?
N2 C14 1.388(3) . ?
N2 C13 1.462(3) . ?
N2 C20 1.453(3) . ?
O1 C4 1.384(3) . ?
O1 C3 1.433(4) . ?
C14 C19 1.398(4) . ?
C14 C15 1.401(3) . ?
C1 H1 0.9800 . ?
C1 C9 1.554(4) . ?
C1 C2 1.529(4) . ?
C11 C10 1.523(3) . ?
C10 H10 0.9800 . ?
C10 C9 1.568(3) . ?
C10 C12 1.521(3) . ?
C9 C4 1.502(4) . ?
C9 C8 1.509(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.524(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C4 C5 1.322(4) . ?
C8 H8 0.9300 . ?
C8 C7 1.340(4) . ?
C7 H7 0.9300 . ?
C7 C6 1.453(4) . ?
C19 H19 0.9300 . ?
C19 C18 1.378(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.369(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.479(4) . ?
C21 C22 1.522(4) . ?
C21 C23 1.530(4) . ?
C21 C24 1.517(4) . ?
C18 H18 0.9300 . ?
C18 C17 1.372(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.485(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C16 H16 0.9300 . ?
C16 C17 1.371(4) . ?
C17 H17 0.9300 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
C1 N1 C21 125.0(2) . . ?
C11 N1 C1 111.1(2) . . ?
C11 N1 C21 123.1(2) . . ?
C14 N2 C13 119.4(2) . . ?
C14 N2 C20 118.0(2) . . ?
C20 N2 C13 115.4(2) . . ?
C4 O1 C3 111.8(2) . . ?
N2 C14 C19 121.8(2) . . ?
N2 C14 C15 121.4(3) . . ?
C19 C14 C15 116.9(3) . . ?
N1 C1 H1 110.3 . . ?
N1 C1 C9 102.8(2) . . ?
N1 C1 C2 110.9(2) . . ?
C9 C1 H1 110.3 . . ?
C2 C1 H1 110.3 . . ?
C2 C1 C9 112.1(2) . . ?
O2 C11 N1 126.4(3) . . ?
O2 C11 C10 124.4(2) . . ?
N1 C11 C10 109.2(2) . . ?
C11 C10 H10 107.4 . . ?
C11 C10 C9 102.5(2) . . ?
C9 C10 H10 107.4 . . ?
C12 C10 C11 112.1(2) . . ?
C12 C10 H10 107.4 . . ?
C12 C10 C9 119.4(2) . . ?
C1 C9 C10 100.04(19) . . ?
C4 C9 C1 112.2(2) . . ?
C4 C9 C10 114.3(2) . . ?
C4 C9 C8 109.2(2) . . ?
C8 C9 C1 110.5(2) . . ?
C8 C9 C10 110.4(2) . . ?
C10 C12 H12A 108.8 . . ?
C10 C12 H12B 108.8 . . ?
C10 C12 C13 113.9(2) . . ?
H12A C12 H12B 107.7 . . ?
C13 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
N2 C13 C12 114.0(2) . . ?
N2 C13 H13A 108.7 . . ?
N2 C13 H13B 108.7 . . ?
C12 C13 H13A 108.7 . . ?
C12 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
O1 C4 C9 115.5(3) . . ?
C5 C4 O1 119.7(3) . . ?
C5 C4 C9 124.8(3) . . ?
C9 C8 H8 118.1 . . ?
C7 C8 C9 123.9(3) . . ?
C7 C8 H8 118.1 . . ?
C8 C7 H7 118.4 . . ?
C8 C7 C6 123.2(3) . . ?
C6 C7 H7 118.4 . . ?
C14 C19 H19 119.5 . . ?
C18 C19 C14 121.0(3) . . ?
C18 C19 H19 119.5 . . ?
C14 C15 H15 119.4 . . ?
C16 C15 C14 121.3(3) . . ?
C16 C15 H15 119.4 . . ?
C4 C5 H5 118.6 . . ?
C4 C5 C6 122.9(3) . . ?
C6 C5 H5 118.6 . . ?
N1 C21 C22 110.8(2) . . ?
N1 C21 C23 108.8(2) . . ?
N1 C21 C24 108.2(3) . . ?
C22 C21 C23 108.3(3) . . ?
C24 C21 C22 109.0(3) . . ?
C24 C21 C23 111.8(3) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 C19 120.9(3) . . ?
C17 C18 H18 119.6 . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C1 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C3 C2 C1 112.1(3) . . ?
C3 C2 H2A 109.2 . . ?
C3 C2 H2B 109.2 . . ?
C7 C6 C5 113.6(3) . . ?
C7 C6 H6A 108.9 . . ?
C7 C6 H6B 108.9 . . ?
C5 C6 H6A 108.9 . . ?
C5 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C15 C16 H16 119.5 . . ?
C15 C16 C17 121.0(3) . . ?
C17 C16 H16 119.5 . . ?
C18 C17 H17 120.5 . . ?
C16 C17 C18 119.0(3) . . ?
C16 C17 H17 120.5 . . ?
O1 C3 C2 112.4(3) . . ?
O1 C3 H3A 109.1 . . ?
O1 C3 H3B 109.1 . . ?
C2 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C11 C10 C9 -161.5(3) . . . . ?
O2 C11 C10 C12 -32.3(4) . . . . ?
N1 C1 C9 C10 36.6(2) . . . . ?
N1 C1 C9 C4 158.1(2) . . . . ?
N1 C1 C9 C8 -79.8(2) . . . . ?
N1 C1 C2 C3 -157.8(3) . . . . ?
N1 C11 C10 C9 18.3(3) . . . . ?
N1 C11 C10 C12 147.5(2) . . . . ?
N2 C14 C19 C18 -179.6(3) . . . . ?
N2 C14 C15 C16 -179.7(3) . . . . ?
O1 C4 C5 C6 -178.4(3) . . . . ?
C14 N2 C13 C12 -66.4(3) . . . . ?
C14 C19 C18 C17 -1.0(5) . . . . ?
C14 C15 C16 C17 -0.5(5) . . . . ?
C1 N1 C11 O2 -174.3(3) . . . . ?
C1 N1 C11 C10 5.9(3) . . . . ?
C1 N1 C21 C22 -11.9(4) . . . . ?
C1 N1 C21 C23 107.1(3) . . . . ?
C1 N1 C21 C24 -131.3(3) . . . . ?
C1 C9 C4 O1 -46.8(3) . . . . ?
C1 C9 C4 C5 137.0(3) . . . . ?
C1 C9 C8 C7 -140.4(3) . . . . ?
C1 C2 C3 O1 54.2(4) . . . . ?
C11 N1 C1 C9 -27.9(3) . . . . ?
C11 N1 C1 C2 92.2(3) . . . . ?
C11 N1 C21 C22 179.0(3) . . . . ?
C11 N1 C21 C23 -62.0(4) . . . . ?
C11 N1 C21 C24 59.6(4) . . . . ?
C11 C10 C9 C1 -33.0(2) . . . . ?
C11 C10 C9 C4 -153.0(2) . . . . ?
C11 C10 C9 C8 83.4(2) . . . . ?
C11 C10 C12 C13 169.0(2) . . . . ?
C10 C9 C4 O1 66.2(3) . . . . ?
C10 C9 C4 C5 -110.0(3) . . . . ?
C10 C9 C8 C7 109.9(3) . . . . ?
C10 C12 C13 N2 -169.1(2) . . . . ?
C9 C1 C2 C3 -43.5(3) . . . . ?
C9 C10 C12 C13 -71.2(3) . . . . ?
C9 C4 C5 C6 -2.4(5) . . . . ?
C9 C8 C7 C6 7.1(4) . . . . ?
C12 C10 C9 C1 -157.6(2) . . . . ?
C12 C10 C9 C4 82.4(3) . . . . ?
C12 C10 C9 C8 -41.1(3) . . . . ?
C13 N2 C14 C19 158.2(2) . . . . ?
C13 N2 C14 C15 -22.3(4) . . . . ?
C4 O1 C3 C2 -61.0(4) . . . . ?
C4 C9 C8 C7 -16.5(4) . . . . ?
C4 C5 C6 C7 -8.7(4) . . . . ?
C8 C9 C4 O1 -169.6(2) . . . . ?
C8 C9 C4 C5 14.2(4) . . . . ?
C8 C7 C6 C5 6.2(4) . . . . ?
C19 C14 C15 C16 -0.1(4) . . . . ?
C19 C18 C17 C16 0.3(5) . . . . ?
C15 C14 C19 C18 0.9(4) . . . . ?
C15 C16 C17 C18 0.4(5) . . . . ?
C21 N1 C1 C9 161.9(2) . . . . ?
C21 N1 C1 C2 -78.1(3) . . . . ?
C21 N1 C11 O2 -3.8(4) . . . . ?
C21 N1 C11 C10 176.4(2) . . . . ?
C20 N2 C14 C19 9.3(4) . . . . ?
C20 N2 C14 C15 -171.2(2) . . . . ?
C20 N2 C13 C12 83.3(3) . . . . ?
C2 C1 C9 C10 -82.6(2) . . . . ?
C2 C1 C9 C4 38.9(3) . . . . ?
C2 C1 C9 C8 161.1(2) . . . . ?
C3 O1 C4 C9 57.5(3) . . . . ?
C3 O1 C4 C5 -126.1(3) . . . . ?

_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 1.373
_oxdiff_exptl_absorpt_empirical_full_min 0.791
####################################################################### 
# 
# 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_11891
_audit_block_doi                 10.5517/ccdc.csd.cc2d3dlj
_database_code_depnum_ccdc_archive 'CCDC 2207807'
loop_
_audit_author_name
_audit_author_address
'guohui zeng'
;South China University of Technology
China
;
_audit_update_record             
;
2022-09-16 deposited with the CCDC.	2024-04-03 downloaded from the CCDC.
;
_audit_creation_date             2022-09-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H29 N3 O'
_chemical_formula_sum            'C21 H29 N3 O'
_chemical_formula_weight         339.47
_chemical_absolute_configuration rmad
_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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.5960(10)
_cell_length_b                   9.6411(12)
_cell_length_c                   14.4759(16)
_cell_angle_alpha                90
_cell_angle_beta                 90.818(13)
_cell_angle_gamma                90
_cell_volume                     920.5(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2322
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.9570
_cell_measurement_theta_min      2.8240
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.03245
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0771
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.871
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7820
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.799
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.439
_diffrn_reflns_theta_min         2.538
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.871
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -1.00  83.00   1.00    1.00    --   15.65  57.00  30.00   84
  2  ω     -7.00  79.00   1.00    1.00    --   15.65  77.00 150.00   86
  3  ω      3.00  40.00   1.00    1.00    --   15.65 -77.00-120.00   37
  4  ω    -14.00  22.00   1.00    1.00    --  -16.59 -99.00  30.00   36
  5  ω    -46.00  26.00   1.00    1.00    --   15.65 -57.00 -90.00   72
  6  ω    -47.00  -9.00   1.00    1.00    --   15.65 -57.00-120.00   38
  7  ω    -51.00 -26.00   1.00    1.00    --   15.65 -77.00-120.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0429386000
_diffrn_orient_matrix_UB_12      0.0519569000
_diffrn_orient_matrix_UB_13      -0.0288484000
_diffrn_orient_matrix_UB_21      -0.0637986000
_diffrn_orient_matrix_UB_22      -0.0503311000
_diffrn_orient_matrix_UB_23      -0.0213352000
_diffrn_orient_matrix_UB_31      -0.0755359000
_diffrn_orient_matrix_UB_32      0.0127572000
_diffrn_orient_matrix_UB_33      0.0333250000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_full    0.936
_reflns_Friedel_fraction_max     0.720
_reflns_number_gt                2729
_reflns_number_total             4069
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 
;
 Flack x determined using 796 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         4069
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0585
_refine_ls_restrained_S_all      1.016
_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)+(0.0475P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1209
_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:
 C2(H2), C4(H4), C17(H17), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C16(H16A,H16B), C14(H14A,H14B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C8(H8), C7(H7)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C21(H21A,H21B,H21C), C15(H15A,H15B,H15C), C20(H20A,H20B,
 H20C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6274(4) 0.4702(3) 0.91926(15) 0.0599(8) Uani 1 1 d . . . . .
N1 N 0.3405(4) 0.5866(3) 0.96255(16) 0.0398(7) Uani 1 1 d . . . . .
N2 N 0.3820(5) 0.3517(3) 0.5981(2) 0.0528(9) Uani 1 1 d . . . . .
N3 N 0.1473(5) 0.6771(3) 0.65495(19) 0.0501(9) Uani 1 1 d . . . . .
H3 H 0.109(6) 0.744(4) 0.614(2) 0.060 Uiso 1 1 d . U . . .
C1 C 0.4789(5) 0.5410(3) 0.9015(2) 0.0397(8) Uani 1 1 d . . . . .
C2 C 0.4183(5) 0.5942(3) 0.80678(19) 0.0373(8) Uani 1 1 d . . . . .
H2 H 0.4798 0.6861 0.8004 0.045 Uiso 1 1 calc R U . . .
C4 C 0.3414(5) 0.3954(3) 0.6923(2) 0.0405(8) Uani 1 1 d . . . . .
H4 H 0.3656 0.3147 0.7321 0.049 Uiso 1 1 calc R U . . .
C13 C 0.1914(5) 0.6167(3) 0.8162(2) 0.0409(8) Uani 1 1 d . . . . .
C5 C 0.2825(6) 0.4125(3) 0.5240(2) 0.0422(9) Uani 1 1 d . . . . .
C17 C 0.1201(5) 0.4334(3) 0.7015(2) 0.0404(8) Uani 1 1 d . . . . .
H17 H 0.0391 0.3498 0.6902 0.049 Uiso 1 1 calc R U . . .
C3 C 0.4873(5) 0.5085(4) 0.7246(2) 0.0440(9) Uani 1 1 d . . . . .
H3A H 0.6160 0.4656 0.7407 0.053 Uiso 1 1 calc R U . . .
H3B H 0.5106 0.5709 0.6733 0.053 Uiso 1 1 calc R U . . .
C11 C 0.0539(5) 0.5425(4) 0.6322(2) 0.0430(9) Uani 1 1 d . . . . .
H11 H -0.0940 0.5518 0.6334 0.052 Uiso 1 1 calc R U . . .
C16 C 0.0836(5) 0.4807(4) 0.7996(2) 0.0444(8) Uani 1 1 d . . . . .
H16A H -0.0607 0.4921 0.8093 0.053 Uiso 1 1 calc R U . . .
H16B H 0.1341 0.4114 0.8428 0.053 Uiso 1 1 calc R U . . .
C10 C 0.1166(5) 0.5011(3) 0.5369(2) 0.0413(8) Uani 1 1 d . . . . .
C6 C 0.3406(7) 0.3825(4) 0.4336(3) 0.0564(11) Uani 1 1 d . . . . .
H6 H 0.4514 0.3251 0.4232 0.068 Uiso 1 1 calc R U . . .
C18 C 0.3407(6) 0.5530(4) 1.0625(2) 0.0439(9) Uani 1 1 d . . . . .
C9 C 0.0126(6) 0.5514(4) 0.4607(2) 0.0524(10) Uani 1 1 d . . . . .
H9 H -0.0992 0.6083 0.4696 0.063 Uiso 1 1 calc R U . . .
C8 C 0.0685(7) 0.5202(4) 0.3721(3) 0.0603(12) Uani 1 1 d . . . . .
H8 H -0.0043 0.5544 0.3215 0.072 Uiso 1 1 calc R U . . .
C14 C 0.1730(6) 0.6596(4) 0.9168(2) 0.0497(10) Uani 1 1 d . . . . .
H14A H 0.1872 0.7593 0.9237 0.060 Uiso 1 1 calc R U . . .
H14B H 0.0436 0.6312 0.9416 0.060 Uiso 1 1 calc R U . . .
C7 C 0.2346(7) 0.4373(4) 0.3603(2) 0.0602(12) Uani 1 1 d . . . . .
H7 H 0.2767 0.4176 0.3007 0.072 Uiso 1 1 calc R U . . .
C12 C 0.1053(7) 0.7216(4) 0.7491(2) 0.0576(11) Uani 1 1 d . . . . .
H12A H -0.0399 0.7298 0.7573 0.069 Uiso 1 1 calc R U . . .
H12B H 0.1662 0.8117 0.7606 0.069 Uiso 1 1 calc R U . . .
C19 C 0.1846(7) 0.6405(4) 1.1116(2) 0.0726(14) Uani 1 1 d . . . . .
H19A H 0.2078 0.7368 1.0984 0.109 Uiso 1 1 calc R U . . .
H19B H 0.1961 0.6253 1.1770 0.109 Uiso 1 1 calc R U . . .
H19C H 0.0511 0.6149 1.0905 0.109 Uiso 1 1 calc R U . . .
C21 C 0.2878(8) 0.4009(4) 1.0706(3) 0.0764(15) Uani 1 1 d . . . . .
H21A H 0.1575 0.3844 1.0424 0.115 Uiso 1 1 calc R U . . .
H21B H 0.2840 0.3753 1.1347 0.115 Uiso 1 1 calc R U . . .
H21C H 0.3884 0.3464 1.0400 0.115 Uiso 1 1 calc R U . . .
C15 C 0.5682(7) 0.2751(5) 0.5850(3) 0.0748(14) Uani 1 1 d . . . . .
H15A H 0.6711 0.3366 0.5627 0.112 Uiso 1 1 calc R U . . .
H15B H 0.5452 0.2024 0.5408 0.112 Uiso 1 1 calc R U . . .
H15C H 0.6119 0.2355 0.6428 0.112 Uiso 1 1 calc R U . . .
C20 C 0.5466(7) 0.5839(5) 1.1050(3) 0.0736(13) Uani 1 1 d . . . . .
H20A H 0.6478 0.5293 1.0748 0.110 Uiso 1 1 calc R U . . .
H20B H 0.5457 0.5614 1.1696 0.110 Uiso 1 1 calc R U . . .
H20C H 0.5771 0.6806 1.0975 0.110 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.218(4) . ?
N1 C1 1.352(4) . ?
N1 C18 1.482(4) . ?
N1 C14 1.461(4) . ?
N2 C4 1.456(4) . ?
N2 C5 1.380(4) . ?
N2 C15 1.448(5) . ?
N3 H3 0.91(4) . ?
N3 C11 1.471(5) . ?
N3 C12 1.460(4) . ?
C1 C2 1.513(4) . ?
C2 H2 0.9800 . ?
C2 C13 1.521(5) . ?
C2 C3 1.522(4) . ?
C4 H4 0.9800 . ?
C4 C17 1.512(5) . ?
C4 C3 1.524(5) . ?
C13 C16 1.510(5) . ?
C13 C14 1.520(4) . ?
C13 C12 1.508(5) . ?
C5 C10 1.403(5) . ?
C5 C6 1.400(5) . ?
C17 H17 0.9800 . ?
C17 C11 1.514(5) . ?
C17 C16 1.514(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C11 H11 0.9800 . ?
C11 C10 1.499(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C10 C9 1.379(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.368(6) . ?
C18 C19 1.516(5) . ?
C18 C21 1.512(5) . ?
C18 C20 1.513(5) . ?
C9 H9 0.9300 . ?
C9 C8 1.373(5) . ?
C8 H8 0.9300 . ?
C8 C7 1.369(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C7 H7 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
C1 N1 C18 125.1(3) . . ?
C1 N1 C14 112.0(2) . . ?
C14 N1 C18 122.5(2) . . ?
C5 N2 C4 120.9(3) . . ?
C5 N2 C15 120.7(3) . . ?
C15 N2 C4 116.0(3) . . ?
C11 N3 H3 111(3) . . ?
C12 N3 H3 110(2) . . ?
C12 N3 C11 112.6(3) . . ?
O1 C1 N1 126.4(3) . . ?
O1 C1 C2 125.6(3) . . ?
N1 C1 C2 108.1(3) . . ?
C1 C2 H2 106.8 . . ?
C1 C2 C13 102.4(2) . . ?
C1 C2 C3 116.5(3) . . ?
C13 C2 H2 106.8 . . ?
C13 C2 C3 116.9(3) . . ?
C3 C2 H2 106.8 . . ?
N2 C4 H4 106.9 . . ?
N2 C4 C17 110.1(3) . . ?
N2 C4 C3 111.7(3) . . ?
C17 C4 H4 106.9 . . ?
C17 C4 C3 113.9(3) . . ?
C3 C4 H4 106.9 . . ?
C16 C13 C2 108.9(3) . . ?
C16 C13 C14 110.2(3) . . ?
C14 C13 C2 102.5(3) . . ?
C12 C13 C2 113.6(3) . . ?
C12 C13 C16 107.9(3) . . ?
C12 C13 C14 113.6(3) . . ?
N2 C5 C10 121.2(3) . . ?
N2 C5 C6 120.3(3) . . ?
C6 C5 C10 118.4(3) . . ?
C4 C17 H17 108.1 . . ?
C4 C17 C11 112.3(3) . . ?
C4 C17 C16 108.8(3) . . ?
C11 C17 H17 108.1 . . ?
C11 C17 C16 111.4(3) . . ?
C16 C17 H17 108.1 . . ?
C2 C3 C4 115.7(3) . . ?
C2 C3 H3A 108.4 . . ?
C2 C3 H3B 108.4 . . ?
C4 C3 H3A 108.4 . . ?
C4 C3 H3B 108.4 . . ?
H3A C3 H3B 107.4 . . ?
N3 C11 C17 110.4(3) . . ?
N3 C11 H11 109.2 . . ?
N3 C11 C10 108.7(3) . . ?
C17 C11 H11 109.2 . . ?
C10 C11 C17 110.1(3) . . ?
C10 C11 H11 109.2 . . ?
C13 C16 C17 109.3(3) . . ?
C13 C16 H16A 109.8 . . ?
C13 C16 H16B 109.8 . . ?
C17 C16 H16A 109.8 . . ?
C17 C16 H16B 109.8 . . ?
H16A C16 H16B 108.3 . . ?
C5 C10 C11 120.7(3) . . ?
C9 C10 C5 119.2(3) . . ?
C9 C10 C11 120.1(3) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.1(4) . . ?
C7 C6 H6 119.9 . . ?
N1 C18 C19 110.2(3) . . ?
N1 C18 C21 106.9(3) . . ?
N1 C18 C20 110.0(3) . . ?
C21 C18 C19 110.1(3) . . ?
C21 C18 C20 111.5(4) . . ?
C20 C18 C19 108.1(3) . . ?
C10 C9 H9 118.9 . . ?
C8 C9 C10 122.3(4) . . ?
C8 C9 H9 118.9 . . ?
C9 C8 H8 121.0 . . ?
C7 C8 C9 118.0(4) . . ?
C7 C8 H8 121.0 . . ?
N1 C14 C13 103.4(2) . . ?
N1 C14 H14A 111.1 . . ?
N1 C14 H14B 111.1 . . ?
C13 C14 H14A 111.1 . . ?
C13 C14 H14B 111.1 . . ?
H14A C14 H14B 109.0 . . ?
C6 C7 C8 122.0(3) . . ?
C6 C7 H7 119.0 . . ?
C8 C7 H7 119.0 . . ?
N3 C12 C13 109.2(3) . . ?
N3 C12 H12A 109.8 . . ?
N3 C12 H12B 109.8 . . ?
C13 C12 H12A 109.8 . . ?
C13 C12 H12B 109.8 . . ?
H12A C12 H12B 108.3 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C13 156.1(3) . . . . ?
O1 C1 C2 C3 27.2(5) . . . . ?
N1 C1 C2 C13 -24.4(3) . . . . ?
N1 C1 C2 C3 -153.3(3) . . . . ?
N2 C4 C17 C11 -55.2(4) . . . . ?
N2 C4 C17 C16 -179.0(3) . . . . ?
N2 C4 C3 C2 160.5(3) . . . . ?
N2 C5 C10 C11 5.5(5) . . . . ?
N2 C5 C10 C9 -175.3(3) . . . . ?
N2 C5 C6 C7 176.6(3) . . . . ?
N3 C11 C10 C5 95.5(4) . . . . ?
N3 C11 C10 C9 -83.7(4) . . . . ?
C1 N1 C18 C19 170.7(3) . . . . ?
C1 N1 C18 C21 -69.6(4) . . . . ?
C1 N1 C18 C20 51.6(5) . . . . ?
C1 N1 C14 C13 16.6(4) . . . . ?
C1 C2 C13 C16 -83.7(3) . . . . ?
C1 C2 C13 C14 33.1(3) . . . . ?
C1 C2 C13 C12 156.0(3) . . . . ?
C1 C2 C3 C4 90.0(4) . . . . ?
C2 C13 C16 C17 -63.1(3) . . . . ?
C2 C13 C14 N1 -30.5(3) . . . . ?
C2 C13 C12 N3 58.0(4) . . . . ?
C4 N2 C5 C10 -10.6(5) . . . . ?
C4 N2 C5 C6 172.0(3) . . . . ?
C4 C17 C11 N3 -69.7(4) . . . . ?
C4 C17 C11 C10 50.3(4) . . . . ?
C4 C17 C16 C13 68.0(3) . . . . ?
C13 C2 C3 C4 -31.5(4) . . . . ?
C5 N2 C4 C17 35.0(4) . . . . ?
C5 N2 C4 C3 -92.6(4) . . . . ?
C5 C10 C9 C8 -1.5(5) . . . . ?
C5 C6 C7 C8 -1.1(6) . . . . ?
C17 C4 C3 C2 34.9(4) . . . . ?
C17 C11 C10 C5 -25.5(4) . . . . ?
C17 C11 C10 C9 155.3(3) . . . . ?
C3 C2 C13 C16 44.9(4) . . . . ?
C3 C2 C13 C14 161.7(3) . . . . ?
C3 C2 C13 C12 -75.3(4) . . . . ?
C3 C4 C17 C11 71.2(3) . . . . ?
C3 C4 C17 C16 -52.6(4) . . . . ?
C11 N3 C12 C13 61.1(4) . . . . ?
C11 C17 C16 C13 -56.3(4) . . . . ?
C11 C10 C9 C8 177.7(3) . . . . ?
C16 C13 C14 N1 85.2(3) . . . . ?
C16 C13 C12 N3 -62.8(4) . . . . ?
C16 C17 C11 N3 52.6(4) . . . . ?
C16 C17 C11 C10 172.6(3) . . . . ?
C10 C5 C6 C7 -1.0(5) . . . . ?
C10 C9 C8 C7 -0.6(6) . . . . ?
C6 C5 C10 C11 -177.0(3) . . . . ?
C6 C5 C10 C9 2.2(5) . . . . ?
C18 N1 C1 O1 -2.7(5) . . . . ?
C18 N1 C1 C2 177.7(3) . . . . ?
C18 N1 C14 C13 -156.3(3) . . . . ?
C9 C8 C7 C6 1.9(6) . . . . ?
C14 N1 C1 O1 -175.4(4) . . . . ?
C14 N1 C1 C2 5.0(4) . . . . ?
C14 N1 C18 C19 -17.3(5) . . . . ?
C14 N1 C18 C21 102.4(4) . . . . ?
C14 N1 C18 C20 -136.5(4) . . . . ?
C14 C13 C16 C17 -174.8(3) . . . . ?
C14 C13 C12 N3 174.7(3) . . . . ?
C12 N3 C11 C17 -55.4(4) . . . . ?
C12 N3 C11 C10 -176.3(3) . . . . ?
C12 C13 C16 C17 60.6(3) . . . . ?
C12 C13 C14 N1 -153.5(3) . . . . ?
C15 N2 C4 C17 -162.7(3) . . . . ?
C15 N2 C4 C3 69.7(4) . . . . ?
C15 N2 C5 C10 -172.0(4) . . . . ?
C15 N2 C5 C6 10.5(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 15.890
_oxdiff_exptl_absorpt_empirical_full_min 0.330
####################################################################### 
# 
# 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_10035
_audit_block_doi                 10.5517/ccdc.csd.cc29wmmg
_database_code_depnum_ccdc_archive 'CCDC 2141716'
loop_
_audit_author_name
_audit_author_address
'guohui zeng'
;South China University of Technology
China
;
_audit_update_record             
;
2022-01-13 deposited with the CCDC.	2024-04-03 downloaded from the CCDC.
;
_audit_creation_date             2021-08-30
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H31 Br N2 O2'
_chemical_formula_sum            'C23 H31 Br N2 O2'
_chemical_formula_weight         446.40
_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'
Br Br -0.2901 2.4595 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_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                   14.2363(17)
_cell_length_b                   12.6108(8)
_cell_length_c                   13.0773(13)
_cell_angle_alpha                90
_cell_angle_beta                 104.172(11)
_cell_angle_gamma                90
_cell_volume                     2276.3(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2123
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.4190
_cell_measurement_theta_min      2.2520
_shelx_estimated_absorpt_T_max   0.811
_shelx_estimated_absorpt_T_min   0.629
_exptl_absorpt_coefficient_mu    1.825
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86063
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             932
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_unetI/netI     0.0689
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9067
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        24.500
_diffrn_reflns_theta_max         24.500
_diffrn_reflns_theta_min         2.187
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.986
_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     -1.00  83.00   1.00   12.50    --   15.49  57.00  60.00   84
  2  ω    -43.00  65.00   1.00   12.50    --   15.49   0.00  30.00  108
  3  ω    -11.00  21.00   1.00   12.50    --  -16.28 -99.00 -90.00   32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0395863000
_diffrn_orient_matrix_UB_12      -0.0019811000
_diffrn_orient_matrix_UB_13      -0.0451311000
_diffrn_orient_matrix_UB_21      -0.0324339000
_diffrn_orient_matrix_UB_22      0.0102217000
_diffrn_orient_matrix_UB_23      0.0321886000
_diffrn_orient_matrix_UB_31      0.0045700000
_diffrn_orient_matrix_UB_32      0.0552951000
_diffrn_orient_matrix_UB_33      -0.0075732000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2501
_reflns_number_total             3741
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.305
_refine_diff_density_min         -0.865
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3741
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1029
_refine_ls_R_factor_gt           0.0637
_refine_ls_restrained_S_all      1.028
_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)+(0.0673P)²+2.9316P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1401
_refine_ls_wR_factor_ref         0.1619
_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
2. Rigid bond restraints
 C20, C21
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.0025
3. Uiso/Uaniso restraints and constraints
Uanis(C20) = Uanis(C23)
Uanis(C22) = Uanis(C23)
4.a Ternary CH refined with riding coordinates:
 C7(H7)
4.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C9(H9A,H9B), C3(H3A,H3B)
4.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2), C14(H14), C18(H18), C15(H15), C16(H16), C17(H17)
4.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C10(H10A,H10B,H10C), C21(H21A,H21B,H21C), C23(H23A,H23B,
 H23C), C22(H22A,H22B,H22C)
;
_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
Br1 Br 0.08614(5) 0.10293(4) 0.65775(5) 0.0590(3) Uani 1 1 d . . . . .
O1 O 0.2232(3) 0.4715(3) 0.9536(3) 0.0603(11) Uani 1 1 d . . . . .
O2 O 0.4199(3) 0.2807(3) 0.6136(4) 0.0711(13) Uani 1 1 d . . . . .
N2 N 0.1185(3) 0.5295(3) 0.5312(3) 0.0462(11) Uani 1 1 d . . . . .
N1 N 0.3918(3) 0.1868(3) 0.7539(4) 0.0492(12) Uani 1 1 d . . . . .
C1 C 0.1333(4) 0.2215(4) 0.7484(4) 0.0383(12) Uani 1 1 d . . . . .
C7 C 0.2603(4) 0.2797(4) 0.6492(4) 0.0353(12) Uani 1 1 d . . . . .
H7 H 0.2232 0.2307 0.5964 0.042 Uiso 1 1 calc R U . . .
C4 C 0.2022(4) 0.3905(4) 0.8824(4) 0.0407(13) Uani 1 1 d . . . . .
C6 C 0.2367(4) 0.2538(3) 0.7572(4) 0.0338(11) Uani 1 1 d . . . . .
C11 C 0.2415(4) 0.3913(4) 0.6058(4) 0.0424(13) Uani 1 1 d . . . . .
H11A H 0.2635 0.3960 0.5414 0.051 Uiso 1 1 calc R U . . .
H11B H 0.2802 0.4403 0.6562 0.051 Uiso 1 1 calc R U . . .
C5 C 0.2615(4) 0.3458(4) 0.8325(4) 0.0412(12) Uani 1 1 d . . . . .
H5 H 0.3239 0.3731 0.8448 0.049 Uiso 1 1 calc R U . . .
C2 C 0.0719(4) 0.2673(4) 0.7955(4) 0.0444(13) Uani 1 1 d . . . . .
H2 H 0.0096 0.2399 0.7846 0.053 Uiso 1 1 calc R U . . .
C12 C 0.1358(4) 0.4269(4) 0.5822(4) 0.0428(13) Uani 1 1 d . . . . .
H12A H 0.0960 0.3744 0.5373 0.051 Uiso 1 1 calc R U . . .
H12B H 0.1156 0.4296 0.6478 0.051 Uiso 1 1 calc R U . . .
C13 C 0.1418(4) 0.6224(4) 0.5878(4) 0.0409(13) Uani 1 1 d . . . . .
C8 C 0.3670(4) 0.2502(4) 0.6689(4) 0.0469(14) Uani 1 1 d . . . . .
C14 C 0.1730(4) 0.6236(4) 0.6981(4) 0.0473(14) Uani 1 1 d . . . . .
H14 H 0.1784 0.5599 0.7349 0.057 Uiso 1 1 calc R U . . .
C9 C 0.3094(4) 0.1632(4) 0.7995(4) 0.0476(14) Uani 1 1 d . . . . .
H9A H 0.3291 0.1640 0.8760 0.057 Uiso 1 1 calc R U . . .
H9B H 0.2815 0.0946 0.7762 0.057 Uiso 1 1 calc R U . . .
C3 C 0.0986(4) 0.3606(4) 0.8648(4) 0.0484(14) Uani 1 1 d . . . . .
H3A H 0.0847 0.3456 0.9324 0.058 Uiso 1 1 calc R U . . .
H3B H 0.0588 0.4203 0.8337 0.058 Uiso 1 1 calc R U . . .
C19 C 0.1111(5) 0.5293(5) 0.4186(4) 0.0630(18) Uani 1 1 d . . . . .
H19A H 0.1732 0.5454 0.4060 0.095 Uiso 1 1 calc R U . . .
H19B H 0.0649 0.5818 0.3851 0.095 Uiso 1 1 calc R U . . .
H19C H 0.0903 0.4607 0.3902 0.095 Uiso 1 1 calc R U . . .
C18 C 0.1334(5) 0.7214(4) 0.5378(5) 0.0576(16) Uani 1 1 d . . . . .
H18 H 0.1131 0.7245 0.4647 0.069 Uiso 1 1 calc R U . . .
C15 C 0.1961(5) 0.7177(5) 0.7536(5) 0.0622(17) Uani 1 1 d . . . . .
H15 H 0.2176 0.7165 0.8267 0.075 Uiso 1 1 calc R U . . .
C20 C 0.4910(7) 0.1441(8) 0.7988(8) 0.1125(18) Uani 1 1 d . U . . .
C16 C 0.1871(5) 0.8131(5) 0.7001(7) 0.073(2) Uani 1 1 d . . . . .
H16 H 0.2034 0.8762 0.7369 0.087 Uiso 1 1 calc R U . . .
C17 C 0.1544(5) 0.8140(5) 0.5938(7) 0.073(2) Uani 1 1 d . . . . .
H17 H 0.1460 0.8785 0.5581 0.087 Uiso 1 1 calc R U . . .
C10 C 0.3206(6) 0.5055(6) 0.9827(6) 0.084(2) Uani 1 1 d . . . . .
H10A H 0.3367 0.5400 0.9239 0.126 Uiso 1 1 calc R U . . .
H10B H 0.3622 0.4453 1.0035 0.126 Uiso 1 1 calc R U . . .
H10C H 0.3291 0.5542 1.0407 0.126 Uiso 1 1 calc R U . . .
C21 C 0.5311(6) 0.0939(8) 0.7154(7) 0.122(4) Uani 1 1 d . U . . .
H21A H 0.4921 0.0337 0.6868 0.183 Uiso 1 1 calc R U . . .
H21B H 0.5964 0.0712 0.7455 0.183 Uiso 1 1 calc R U . . .
H21C H 0.5305 0.1444 0.6603 0.183 Uiso 1 1 calc R U . . .
C23 C 0.4923(6) 0.0697(7) 0.8877(7) 0.1125(18) Uani 1 1 d . . . . .
H23A H 0.4697 0.1058 0.9418 0.169 Uiso 1 1 calc R U . . .
H23B H 0.5572 0.0449 0.9161 0.169 Uiso 1 1 calc R U . . .
H23C H 0.4507 0.0104 0.8625 0.169 Uiso 1 1 calc R U . . .
C22 C 0.5564(6) 0.2362(7) 0.8471(7) 0.1125(18) Uani 1 1 d . . . . .
H22A H 0.5680 0.2807 0.7919 0.169 Uiso 1 1 calc R U . . .
H22B H 0.6170 0.2090 0.8881 0.169 Uiso 1 1 calc R U . . .
H22C H 0.5255 0.2768 0.8917 0.169 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
Br1 C1 1.924(5) . ?
O1 C4 1.365(6) . ?
O1 C10 1.411(8) . ?
O2 C8 1.227(6) . ?
N2 C12 1.448(6) . ?
N2 C13 1.383(6) . ?
N2 C19 1.450(6) . ?
N1 C8 1.345(7) . ?
N1 C9 1.470(7) . ?
N1 C20 1.491(9) . ?
C1 C6 1.505(7) . ?
C1 C2 1.319(7) . ?
C7 H7 0.9800 . ?
C7 C6 1.564(6) . ?
C7 C11 1.516(6) . ?
C7 C8 1.523(7) . ?
C4 C5 1.314(7) . ?
C4 C3 1.484(8) . ?
C6 C5 1.506(7) . ?
C6 C9 1.551(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.528(7) . ?
C5 H5 0.9300 . ?
C2 H2 0.9300 . ?
C2 C3 1.478(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.401(7) . ?
C13 C18 1.401(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.388(8) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C18 H18 0.9300 . ?
C18 C17 1.372(9) . ?
C15 H15 0.9300 . ?
C15 C16 1.382(9) . ?
C20 C21 1.490(12) . ?
C20 C23 1.491(12) . ?
C20 C22 1.525(13) . ?
C16 H16 0.9300 . ?
C16 C17 1.355(9) . ?
C17 H17 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
C4 O1 C10 116.7(5) . . ?
C12 N2 C19 115.4(4) . . ?
C13 N2 C12 121.2(4) . . ?
C13 N2 C19 119.6(4) . . ?
C8 N1 C9 112.5(4) . . ?
C8 N1 C20 124.9(6) . . ?
C9 N1 C20 122.7(6) . . ?
C6 C1 Br1 116.4(3) . . ?
C2 C1 Br1 117.2(4) . . ?
C2 C1 C6 126.4(5) . . ?
C6 C7 H7 107.9 . . ?
C11 C7 H7 107.9 . . ?
C11 C7 C6 118.3(4) . . ?
C11 C7 C8 111.5(4) . . ?
C8 C7 H7 107.9 . . ?
C8 C7 C6 102.9(4) . . ?
O1 C4 C3 109.9(4) . . ?
C5 C4 O1 126.8(5) . . ?
C5 C4 C3 123.3(5) . . ?
C1 C6 C7 114.2(4) . . ?
C1 C6 C5 109.1(4) . . ?
C1 C6 C9 112.5(4) . . ?
C5 C6 C7 111.2(4) . . ?
C5 C6 C9 107.7(4) . . ?
C9 C6 C7 101.7(4) . . ?
C7 C11 H11A 108.5 . . ?
C7 C11 H11B 108.5 . . ?
C7 C11 C12 115.0(4) . . ?
H11A C11 H11B 107.5 . . ?
C12 C11 H11A 108.5 . . ?
C12 C11 H11B 108.5 . . ?
C4 C5 C6 125.3(5) . . ?
C4 C5 H5 117.3 . . ?
C6 C5 H5 117.3 . . ?
C1 C2 H2 118.8 . . ?
C1 C2 C3 122.3(5) . . ?
C3 C2 H2 118.8 . . ?
N2 C12 C11 113.9(4) . . ?
N2 C12 H12A 108.8 . . ?
N2 C12 H12B 108.8 . . ?
C11 C12 H12A 108.8 . . ?
C11 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
N2 C13 C14 122.3(4) . . ?
N2 C13 C18 121.6(5) . . ?
C18 C13 C14 116.1(5) . . ?
O2 C8 N1 126.8(5) . . ?
O2 C8 C7 123.7(5) . . ?
N1 C8 C7 109.5(4) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 C13 121.4(5) . . ?
C15 C14 H14 119.3 . . ?
N1 C9 C6 103.6(4) . . ?
N1 C9 H9A 111.0 . . ?
N1 C9 H9B 111.0 . . ?
C6 C9 H9A 111.0 . . ?
C6 C9 H9B 111.0 . . ?
H9A C9 H9B 109.0 . . ?
C4 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
C2 C3 C4 113.2(4) . . ?
C2 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
N2 C19 H19A 109.5 . . ?
N2 C19 H19B 109.5 . . ?
N2 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C13 C18 H18 119.1 . . ?
C17 C18 C13 121.8(6) . . ?
C17 C18 H18 119.1 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.0(6) . . ?
C16 C15 H15 120.0 . . ?
N1 C20 C22 108.2(7) . . ?
C21 C20 N1 111.1(7) . . ?
C21 C20 C23 111.7(8) . . ?
C21 C20 C22 108.8(9) . . ?
C23 C20 N1 111.3(8) . . ?
C23 C20 C22 105.5(8) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.5(6) . . ?
C17 C16 H16 120.2 . . ?
C18 C17 H17 119.5 . . ?
C16 C17 C18 121.0(6) . . ?
C16 C17 H17 119.5 . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C1 C6 C7 56.0(5) . . . . ?
Br1 C1 C6 C5 -178.9(3) . . . . ?
Br1 C1 C6 C9 -59.4(5) . . . . ?
Br1 C1 C2 C3 -178.4(4) . . . . ?
O1 C4 C5 C6 177.7(4) . . . . ?
O1 C4 C3 C2 -175.1(4) . . . . ?
N2 C13 C14 C15 -180.0(5) . . . . ?
N2 C13 C18 C17 178.5(6) . . . . ?
C1 C6 C5 C4 -0.1(7) . . . . ?
C1 C6 C9 N1 152.5(4) . . . . ?
C1 C2 C3 C4 -4.8(7) . . . . ?
C7 C6 C5 C4 126.8(5) . . . . ?
C7 C6 C9 N1 29.8(5) . . . . ?
C7 C11 C12 N2 -174.2(4) . . . . ?
C6 C1 C2 C3 0.5(8) . . . . ?
C6 C7 C11 C12 -61.9(6) . . . . ?
C6 C7 C8 O2 -162.3(5) . . . . ?
C6 C7 C8 N1 18.0(5) . . . . ?
C11 C7 C6 C1 86.4(5) . . . . ?
C11 C7 C6 C5 -37.7(6) . . . . ?
C11 C7 C6 C9 -152.2(5) . . . . ?
C11 C7 C8 O2 -34.5(7) . . . . ?
C11 C7 C8 N1 145.8(4) . . . . ?
C5 C4 C3 C2 6.9(7) . . . . ?
C5 C6 C9 N1 -87.2(5) . . . . ?
C2 C1 C6 C7 -123.0(5) . . . . ?
C2 C1 C6 C5 2.2(7) . . . . ?
C2 C1 C6 C9 121.7(5) . . . . ?
C12 N2 C13 C14 -7.3(8) . . . . ?
C12 N2 C13 C18 174.1(5) . . . . ?
C13 N2 C12 C11 -77.9(6) . . . . ?
C13 C14 C15 C16 0.9(9) . . . . ?
C13 C18 C17 C16 2.1(10) . . . . ?
C8 N1 C9 C6 -20.7(6) . . . . ?
C8 N1 C20 C21 -50.3(11) . . . . ?
C8 N1 C20 C23 -175.5(7) . . . . ?
C8 N1 C20 C22 69.1(9) . . . . ?
C8 C7 C6 C1 -150.2(4) . . . . ?
C8 C7 C6 C5 85.8(5) . . . . ?
C8 C7 C6 C9 -28.7(5) . . . . ?
C8 C7 C11 C12 179.1(4) . . . . ?
C14 C13 C18 C17 -0.2(9) . . . . ?
C14 C15 C16 C17 1.0(10) . . . . ?
C9 N1 C8 O2 -178.1(6) . . . . ?
C9 N1 C8 C7 1.6(6) . . . . ?
C9 N1 C20 C21 129.8(8) . . . . ?
C9 N1 C20 C23 4.6(11) . . . . ?
C9 N1 C20 C22 -110.8(8) . . . . ?
C9 C6 C5 C4 -122.5(5) . . . . ?
C3 C4 C5 C6 -4.6(8) . . . . ?
C19 N2 C12 C11 79.9(6) . . . . ?
C19 N2 C13 C14 -164.1(5) . . . . ?
C19 N2 C13 C18 17.3(8) . . . . ?
C18 C13 C14 C15 -1.3(8) . . . . ?
C15 C16 C17 C18 -2.5(11) . . . . ?
C20 N1 C8 O2 2.0(10) . . . . ?
C20 N1 C8 C7 -178.3(6) . . . . ?
C20 N1 C9 C6 159.2(6) . . . . ?
C10 O1 C4 C5 -5.2(8) . . . . ?
C10 O1 C4 C3 177.0(5) . . . . ?


_olex2_date_sample_data_collection 2021-08-25
_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 1.288
_oxdiff_exptl_absorpt_empirical_full_min 0.868
####################################################################### 
# 
# 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_13794_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2hjtyt
_database_code_depnum_ccdc_archive 'CCDC 2310087'
loop_
_audit_author_name
_audit_author_address
'guohui zeng'
;South China University of Technology
China
;
_audit_update_record             
;
2023-11-24 deposited with the CCDC.	2024-04-03 downloaded from the CCDC.
;
_audit_creation_date             2023-11-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H38 N2 O'
_chemical_formula_sum            'C26 H38 N2 O'
_chemical_formula_weight         394.58
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_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                   21.1618(17)
_cell_length_b                   12.6995(9)
_cell_length_c                   18.3176(14)
_cell_angle_alpha                90
_cell_angle_beta                 100.330(8)
_cell_angle_gamma                90
_cell_volume                     4843.0(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2391
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.5870
_cell_measurement_theta_min      2.7110
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.988
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97231
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.99a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.082
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_av_unetI/netI     0.1373
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18399
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        24.498
_diffrn_reflns_theta_max         24.498
_diffrn_reflns_theta_min         2.281
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     39.00  64.00   1.00   10.00    --   16.96 178.00  90.00   25
  2  ω     60.00  86.00   1.00   10.00    --   16.96 178.00 150.00   26
  3  ω      9.00  56.00   1.00   10.00    --   16.96 -99.00 -60.00   47
  4  ω    -47.00  87.00   1.00   10.00    --   16.96   0.00-180.00  134
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0307469000
_diffrn_orient_matrix_UB_12      -0.0232048000
_diffrn_orient_matrix_UB_13      -0.0020393000
_diffrn_orient_matrix_UB_21      0.0125841000
_diffrn_orient_matrix_UB_22      -0.0343965000
_diffrn_orient_matrix_UB_23      0.0295579000
_diffrn_orient_matrix_UB_31      -0.0075182000
_diffrn_orient_matrix_UB_32      0.0373932000
_diffrn_orient_matrix_UB_33      0.0259171000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3179
_reflns_number_total             7997
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.736
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.955
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     519
_refine_ls_number_reflns         7997
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.1890
_refine_ls_R_factor_gt           0.0908
_refine_ls_restrained_S_all      0.963
_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)+(0.1366P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2398
_refine_ls_wR_factor_ref         0.3041
_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
2. Rigid bond restraints
 C31, C32
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C34, C31
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 C31, C33
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C5, C7
 with sigma for 1-2 distances of 0.0005 and sigma for 1-3 distances of 0.001
 C5, N1
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
3. Uiso/Uaniso restraints and constraints
Uanis(C32) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C33) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C7) = Uanis(C33)
Uanis(C8) = Uanis(C32)
Uanis(C31) = Uanis(C5)
4.a Ternary CH refined with riding coordinates:
 C2(H2), C20(H20), C28(H28), C46(H46)
4.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C9(H9A,H9B), C10(H10A,H10B), C30(H30A,H30B), C35(H35A,H35B),
 C36(H36A,H36B)
4.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C18(H18), C19(H19),
 C21(H21), C22(H22), C38(H38), C39(H39), C40(H40), C41(H41), C42(H42), C44(H44),
  C45(H45), C47(H47), C48(H48)
4.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C17(H17A,H17B,H17C),
 C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C32(H32A,H32B,
 H32C), C33(H33A,H33B,H33C), C34(H34A,H34B,H34C), C43(H43A,H43B,H43C), C50(H50A,
 H50B,H50C), C51(H51A,H51B,H51C), C52(H52A,H52B,H52C)
;
_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
C1 C 0.0704(2) 0.3337(4) 0.4538(2) 0.0499(11) Uani 1 1 d . . . . .
C2 C 0.1115(2) 0.4158(3) 0.4246(2) 0.0460(11) Uani 1 1 d . . . . .
H2 H 0.1418 0.3783 0.3993 0.055 Uiso 1 1 calc R U . . .
C3 C 0.1506(2) 0.4650(3) 0.4955(2) 0.0481(11) Uani 1 1 d . . . . .
C4 C 0.1584(2) 0.3662(4) 0.5463(2) 0.0599(13) Uani 1 1 d . . . . .
H4A H 0.1969 0.3276 0.5412 0.072 Uiso 1 1 calc R U . . .
H4B H 0.1611 0.3863 0.5978 0.072 Uiso 1 1 calc R U . . .
C5 C 0.0807(3) 0.2188(4) 0.5697(3) 0.0681(9) Uani 1 1 d . U . . .
C6 C 0.0329(3) 0.2655(5) 0.6114(3) 0.099(2) Uani 1 1 d . . . . .
H6A H 0.0527 0.3213 0.6427 0.149 Uiso 1 1 calc R U . . .
H6B H 0.0179 0.2121 0.6413 0.149 Uiso 1 1 calc R U . . .
H6C H -0.0028 0.2931 0.5769 0.149 Uiso 1 1 calc R U . . .
C7 C 0.0496(4) 0.1267(5) 0.5228(4) 0.137(2) Uani 1 1 d . U . . .
H7A H 0.0098 0.1494 0.4932 0.205 Uiso 1 1 calc R U . . .
H7B H 0.0415 0.0703 0.5548 0.205 Uiso 1 1 calc R U . . .
H7C H 0.0780 0.1026 0.4909 0.205 Uiso 1 1 calc R U . . .
C8 C 0.1387(3) 0.1748(6) 0.6215(4) 0.147(2) Uani 1 1 d . . . . .
H8A H 0.1710 0.1553 0.5933 0.221 Uiso 1 1 calc R U . . .
H8B H 0.1262 0.1139 0.6465 0.221 Uiso 1 1 calc R U . . .
H8C H 0.1557 0.2273 0.6574 0.221 Uiso 1 1 calc R U . . .
C9 C 0.0740(2) 0.4923(3) 0.3686(2) 0.0520(12) Uani 1 1 d . . . . .
H9A H 0.0988 0.5564 0.3675 0.062 Uiso 1 1 calc R U . . .
H9B H 0.0340 0.5108 0.3843 0.062 Uiso 1 1 calc R U . . .
C10 C 0.0592(2) 0.4449(4) 0.2902(2) 0.0575(13) Uani 1 1 d . . . . .
H10A H 0.0994 0.4253 0.2753 0.069 Uiso 1 1 calc R U . . .
H10B H 0.0342 0.3811 0.2917 0.069 Uiso 1 1 calc R U . . .
C11 C -0.0411(2) 0.5301(4) 0.2306(2) 0.0556(12) Uani 1 1 d . . . . .
C12 C -0.0744(3) 0.6086(4) 0.1859(3) 0.0688(14) Uani 1 1 d . . . . .
H12 H -0.0519 0.6540 0.1599 0.083 Uiso 1 1 calc R U . . .
C13 C -0.1399(3) 0.6198(5) 0.1795(3) 0.0854(17) Uani 1 1 d . . . . .
H13 H -0.1610 0.6721 0.1488 0.102 Uiso 1 1 calc R U . . .
C14 C -0.1743(3) 0.5556(5) 0.2173(3) 0.0864(17) Uani 1 1 d . . . . .
H14 H -0.2185 0.5640 0.2127 0.104 Uiso 1 1 calc R U . . .
C15 C -0.1432(3) 0.4788(4) 0.2620(3) 0.0739(15) Uani 1 1 d . . . . .
H15 H -0.1666 0.4344 0.2875 0.089 Uiso 1 1 calc R U . . .
C16 C -0.0772(2) 0.4658(4) 0.2698(2) 0.0599(13) Uani 1 1 d . . . . .
H16 H -0.0567 0.4140 0.3014 0.072 Uiso 1 1 calc R U . . .
C17 C 0.0615(3) 0.6002(4) 0.2088(3) 0.0864(18) Uani 1 1 d . . . . .
H17A H 0.0447 0.6147 0.1575 0.130 Uiso 1 1 calc R U . . .
H17B H 0.1056 0.5792 0.2140 0.130 Uiso 1 1 calc R U . . .
H17C H 0.0585 0.6624 0.2378 0.130 Uiso 1 1 calc R U . . .
C18 C 0.1126(2) 0.5480(3) 0.5271(2) 0.0462(11) Uani 1 1 d . . . . .
H18 H 0.0719 0.5302 0.5355 0.055 Uiso 1 1 calc R U . . .
C19 C 0.1333(2) 0.6444(4) 0.5437(2) 0.0553(12) Uani 1 1 d . . . . .
H19 H 0.1058 0.6901 0.5623 0.066 Uiso 1 1 calc R U . . .
C20 C 0.1982(2) 0.6865(3) 0.5347(3) 0.0567(12) Uani 1 1 d . . . . .
H20 H 0.2217 0.7003 0.5850 0.068 Uiso 1 1 calc R U . . .
C21 C 0.2354(2) 0.6032(4) 0.5029(2) 0.0555(12) Uani 1 1 d . . . . .
H21 H 0.2764 0.6203 0.4952 0.067 Uiso 1 1 calc R U . . .
C22 C 0.2141(2) 0.5073(4) 0.4850(2) 0.0520(12) Uani 1 1 d . . . . .
H22 H 0.2408 0.4625 0.4642 0.062 Uiso 1 1 calc R U . . .
C23 C 0.1960(2) 0.7931(4) 0.4923(3) 0.0639(13) Uani 1 1 d . . . . .
C24 C 0.1595(3) 0.7785(4) 0.4126(3) 0.0853(17) Uani 1 1 d . . . . .
H24A H 0.1582 0.8443 0.3865 0.128 Uiso 1 1 calc R U . . .
H24B H 0.1165 0.7555 0.4137 0.128 Uiso 1 1 calc R U . . .
H24C H 0.1811 0.7268 0.3877 0.128 Uiso 1 1 calc R U . . .
C25 C 0.1623(3) 0.8767(4) 0.5313(4) 0.105(2) Uani 1 1 d . . . . .
H25A H 0.1663 0.9440 0.5088 0.158 Uiso 1 1 calc R U . . .
H25B H 0.1817 0.8796 0.5828 0.158 Uiso 1 1 calc R U . . .
H25C H 0.1177 0.8591 0.5269 0.158 Uiso 1 1 calc R U . . .
C26 C 0.2645(3) 0.8308(4) 0.4897(4) 0.0948(19) Uani 1 1 d . . . . .
H26A H 0.2845 0.7829 0.4603 0.142 Uiso 1 1 calc R U . . .
H26B H 0.2890 0.8333 0.5391 0.142 Uiso 1 1 calc R U . . .
H26C H 0.2629 0.8998 0.4680 0.142 Uiso 1 1 calc R U . . .
N1 N 0.10130(17) 0.3024(3) 0.5214(2) 0.0582(9) Uani 1 1 d . U . . .
N2 N 0.02432(19) 0.5154(3) 0.2347(2) 0.0610(11) Uani 1 1 d . . . . .
O1 O 0.01801(15) 0.3020(2) 0.42194(15) 0.0567(8) Uani 1 1 d . . . . .
C27 C 0.4272(2) 0.5239(4) 0.7816(3) 0.0577(13) Uani 1 1 d . . . . .
C28 C 0.3909(2) 0.6040(3) 0.8204(2) 0.0501(11) Uani 1 1 d . . . . .
H28 H 0.3621 0.5649 0.8470 0.060 Uiso 1 1 calc R U . . .
C29 C 0.34850(19) 0.6612(3) 0.7541(2) 0.0477(11) Uani 1 1 d . . . . .
C30 C 0.3338(2) 0.5696(3) 0.6992(3) 0.0608(13) Uani 1 1 d . . . . .
H30A H 0.2961 0.5312 0.7075 0.073 Uiso 1 1 calc R U . . .
H30B H 0.3265 0.5950 0.6484 0.073 Uiso 1 1 calc R U . . .
C31 C 0.4028(3) 0.4165(4) 0.6639(3) 0.0681(9) Uani 1 1 d . U . . .
C32 C 0.3430(3) 0.3825(6) 0.6169(5) 0.147(2) Uani 1 1 d . U . . .
H32A H 0.3099 0.3771 0.6463 0.221 Uiso 1 1 calc R U . . .
H32B H 0.3494 0.3151 0.5957 0.221 Uiso 1 1 calc R U . . .
H32C H 0.3306 0.4329 0.5780 0.221 Uiso 1 1 calc R U . . .
C33 C 0.4541(4) 0.4494(5) 0.6232(4) 0.137(2) Uani 1 1 d . U . . .
H33A H 0.4729 0.3881 0.6051 0.205 Uiso 1 1 calc R U . . .
H33B H 0.4865 0.4878 0.6560 0.205 Uiso 1 1 calc R U . . .
H33C H 0.4360 0.4935 0.5822 0.205 Uiso 1 1 calc R U . . .
C34 C 0.4260(4) 0.3203(4) 0.7061(4) 0.121(2) Uani 1 1 d . U . . .
H34A H 0.4662 0.3349 0.7381 0.181 Uiso 1 1 calc R U . . .
H34B H 0.4319 0.2651 0.6721 0.181 Uiso 1 1 calc R U . . .
H34C H 0.3950 0.2985 0.7354 0.181 Uiso 1 1 calc R U . . .
C35 C 0.4336(2) 0.6715(3) 0.8761(2) 0.0541(12) Uani 1 1 d . . . . .
H35A H 0.4102 0.7340 0.8859 0.065 Uiso 1 1 calc R U . . .
H35B H 0.4704 0.6940 0.8551 0.065 Uiso 1 1 calc R U . . .
C36 C 0.4575(2) 0.6140(4) 0.9496(2) 0.0663(14) Uani 1 1 d . . . . .
H36A H 0.4208 0.5950 0.9717 0.080 Uiso 1 1 calc R U . . .
H36B H 0.4786 0.5493 0.9392 0.080 Uiso 1 1 calc R U . . .
C37 C 0.5667(3) 0.6646(4) 1.0096(3) 0.0614(13) Uani 1 1 d . . . . .
C38 C 0.6087(3) 0.7045(5) 1.0698(3) 0.0864(18) Uani 1 1 d . . . . .
H38 H 0.5922 0.7396 1.1068 0.104 Uiso 1 1 calc R U . . .
C39 C 0.6743(4) 0.6941(5) 1.0769(4) 0.103(2) Uani 1 1 d . . . . .
H39 H 0.7009 0.7254 1.1169 0.123 Uiso 1 1 calc R U . . .
C40 C 0.7007(3) 0.6390(5) 1.0268(4) 0.0951(19) Uani 1 1 d . . . . .
H40 H 0.7449 0.6295 1.0327 0.114 Uiso 1 1 calc R U . . .
C41 C 0.6599(3) 0.5976(4) 0.9669(3) 0.0796(16) Uani 1 1 d . . . . .
H41 H 0.6770 0.5591 0.9319 0.096 Uiso 1 1 calc R U . . .
C42 C 0.5954(3) 0.6112(4) 0.9573(3) 0.0620(13) Uani 1 1 d . . . . .
H42 H 0.5696 0.5843 0.9149 0.074 Uiso 1 1 calc R U . . .
C43 C 0.4741(3) 0.7345(6) 1.0557(3) 0.116(2) Uani 1 1 d . . . . .
H43A H 0.4912 0.7097 1.1048 0.175 Uiso 1 1 calc R U . . .
H43B H 0.4283 0.7261 1.0461 0.175 Uiso 1 1 calc R U . . .
H43C H 0.4846 0.8076 1.0519 0.175 Uiso 1 1 calc R U . . .
C44 C 0.2883(2) 0.7074(4) 0.7725(2) 0.0553(12) Uani 1 1 d . . . . .
H44 H 0.2614 0.6631 0.7933 0.066 Uiso 1 1 calc R U . . .
C45 C 0.2708(2) 0.8060(4) 0.7613(3) 0.0614(13) Uani 1 1 d . . . . .
H45 H 0.2311 0.8247 0.7723 0.074 Uiso 1 1 calc R U . . .
C46 C 0.3082(2) 0.8908(4) 0.7328(2) 0.0587(13) Uani 1 1 d . . . . .
H46 H 0.2824 0.9145 0.6859 0.070 Uiso 1 1 calc R U . . .
C47 C 0.3696(2) 0.8452(4) 0.7139(2) 0.0584(13) Uani 1 1 d . . . . .
H47 H 0.3970 0.8906 0.6947 0.070 Uiso 1 1 calc R U . . .
C48 C 0.3868(2) 0.7450(3) 0.7229(2) 0.0517(11) Uani 1 1 d . . . . .
H48 H 0.4252 0.7249 0.7090 0.062 Uiso 1 1 calc R U . . .
C49 C 0.3195(3) 0.9899(3) 0.7844(3) 0.0654(14) Uani 1 1 d . . . . .
C50 C 0.2528(3) 1.0368(4) 0.7899(3) 0.0942(19) Uani 1 1 d . . . . .
H50A H 0.2280 1.0454 0.7409 0.141 Uiso 1 1 calc R U . . .
H50B H 0.2583 1.1039 0.8142 0.141 Uiso 1 1 calc R U . . .
H50C H 0.2306 0.9899 0.8179 0.141 Uiso 1 1 calc R U . . .
C51 C 0.3593(4) 1.0720(4) 0.7518(3) 0.114(2) Uani 1 1 d . . . . .
H51A H 0.4007 1.0431 0.7490 0.171 Uiso 1 1 calc R U . . .
H51B H 0.3645 1.1333 0.7830 0.171 Uiso 1 1 calc R U . . .
H51C H 0.3377 1.0912 0.7030 0.171 Uiso 1 1 calc R U . . .
C52 C 0.3542(3) 0.9595(4) 0.8610(3) 0.0783(16) Uani 1 1 d . . . . .
H52A H 0.3309 0.9046 0.8805 0.117 Uiso 1 1 calc R U . . .
H52B H 0.3573 1.0198 0.8931 0.117 Uiso 1 1 calc R U . . .
H52C H 0.3966 0.9349 0.8580 0.117 Uiso 1 1 calc R U . . .
N3 N 0.39113(18) 0.5025(3) 0.7141(2) 0.0619(11) Uani 1 1 d . . . . .
N4 N 0.5015(2) 0.6749(4) 1.0025(2) 0.0718(12) Uani 1 1 d . . . . .
O2 O 0.47972(16) 0.4871(3) 0.80629(19) 0.0751(10) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.515(6) . ?
C1 N1 1.352(5) . ?
C1 O1 1.225(5) . ?
C2 H2 0.9800 . ?
C2 C3 1.542(5) . ?
C2 C9 1.527(5) . ?
C3 C4 1.553(6) . ?
C3 C18 1.503(6) . ?
C3 C22 1.492(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 N1 1.458(5) . ?
C5 C6 1.494(7) . ?
C5 C7 1.528(7) . ?
C5 C8 1.518(7) . ?
C5 N1 1.497(6) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.538(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 N2 1.453(5) . ?
C11 C12 1.398(6) . ?
C11 C16 1.401(6) . ?
C11 N2 1.386(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.377(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.363(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.364(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.389(7) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C17 N2 1.462(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.317(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.509(6) . ?
C20 H20 0.9800 . ?
C20 C21 1.497(6) . ?
C20 C23 1.558(6) . ?
C21 H21 0.9300 . ?
C21 C22 1.320(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.536(7) . ?
C23 C25 1.525(7) . ?
C23 C26 1.537(7) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 C28 1.525(6) . ?
C27 N3 1.359(6) . ?
C27 O2 1.215(5) . ?
C28 H28 0.9800 . ?
C28 C29 1.554(6) . ?
C28 C35 1.505(6) . ?
C29 C30 1.532(6) . ?
C29 C44 1.495(6) . ?
C29 C48 1.511(6) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C30 N3 1.467(5) . ?
C31 C32 1.462(8) . ?
C31 C33 1.482(8) . ?
C31 C34 1.482(7) . ?
C31 N3 1.477(6) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C35 C36 1.536(6) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C36 N4 1.443(6) . ?
C37 C38 1.385(7) . ?
C37 C42 1.398(6) . ?
C37 N4 1.367(6) . ?
C38 H38 0.9300 . ?
C38 C39 1.376(8) . ?
C39 H39 0.9300 . ?
C39 C40 1.351(8) . ?
C40 H40 0.9300 . ?
C40 C41 1.373(8) . ?
C41 H41 0.9300 . ?
C41 C42 1.356(7) . ?
C42 H42 0.9300 . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?
C43 N4 1.437(6) . ?
C44 H44 0.9300 . ?
C44 C45 1.312(6) . ?
C45 H45 0.9300 . ?
C45 C46 1.485(6) . ?
C46 H46 0.9800 . ?
C46 C47 1.519(6) . ?
C46 C49 1.566(6) . ?
C47 H47 0.9300 . ?
C47 C48 1.325(6) . ?
C48 H48 0.9300 . ?
C49 C50 1.552(7) . ?
C49 C51 1.528(7) . ?
C49 C52 1.513(6) . ?
C50 H50A 0.9600 . ?
C50 H50B 0.9600 . ?
C50 H50C 0.9600 . ?
C51 H51A 0.9600 . ?
C51 H51B 0.9600 . ?
C51 H51C 0.9600 . ?
C52 H52A 0.9600 . ?
C52 H52B 0.9600 . ?
C52 H52C 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
N1 C1 C2 108.2(4) . . ?
O1 C1 C2 125.9(4) . . ?
O1 C1 N1 125.9(4) . . ?
C1 C2 H2 107.3 . . ?
C1 C2 C3 103.7(3) . . ?
C1 C2 C9 114.4(4) . . ?
C3 C2 H2 107.3 . . ?
C9 C2 H2 107.3 . . ?
C9 C2 C3 116.3(3) . . ?
C2 C3 C4 99.3(3) . . ?
C18 C3 C2 111.4(3) . . ?
C18 C3 C4 110.0(3) . . ?
C22 C3 C2 113.4(3) . . ?
C22 C3 C4 111.6(4) . . ?
C22 C3 C18 110.7(4) . . ?
C3 C4 H4A 110.6 . . ?
C3 C4 H4B 110.6 . . ?
H4A C4 H4B 108.7 . . ?
N1 C4 C3 105.6(3) . . ?
N1 C4 H4A 110.6 . . ?
N1 C4 H4B 110.6 . . ?
C6 C5 C7 109.2(5) . . ?
C6 C5 C8 111.9(5) . . ?
C6 C5 N1 108.5(4) . . ?
C8 C5 C7 106.7(5) . . ?
N1 C5 C7 110.6(4) . . ?
N1 C5 C8 110.0(5) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C2 C9 H9A 109.3 . . ?
C2 C9 H9B 109.3 . . ?
C2 C9 C10 111.8(3) . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C9 C10 H10A 108.8 . . ?
C9 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
N2 C10 C9 113.8(4) . . ?
N2 C10 H10A 108.8 . . ?
N2 C10 H10B 108.8 . . ?
C12 C11 C16 116.9(5) . . ?
N2 C11 C12 121.5(4) . . ?
N2 C11 C16 121.6(4) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 C11 121.2(5) . . ?
C13 C12 H12 119.4 . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 121.0(5) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 120.3 . . ?
C13 C14 C15 119.3(5) . . ?
C15 C14 H14 120.3 . . ?
C14 C15 H15 119.5 . . ?
C14 C15 C16 121.0(5) . . ?
C16 C15 H15 119.5 . . ?
C11 C16 H16 119.7 . . ?
C15 C16 C11 120.6(5) . . ?
C15 C16 H16 119.7 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
N2 C17 H17C 109.5 . . ?
C3 C18 H18 117.9 . . ?
C19 C18 C3 124.2(4) . . ?
C19 C18 H18 117.9 . . ?
C18 C19 H19 117.4 . . ?
C18 C19 C20 125.2(4) . . ?
C20 C19 H19 117.4 . . ?
C19 C20 H20 106.2 . . ?
C19 C20 C23 114.5(4) . . ?
C21 C20 C19 110.1(4) . . ?
C21 C20 H20 106.2 . . ?
C21 C20 C23 113.0(4) . . ?
C23 C20 H20 106.2 . . ?
C20 C21 H21 117.6 . . ?
C22 C21 C20 124.7(4) . . ?
C22 C21 H21 117.6 . . ?
C3 C22 H22 117.4 . . ?
C21 C22 C3 125.1(4) . . ?
C21 C22 H22 117.4 . . ?
C24 C23 C20 109.6(4) . . ?
C24 C23 C26 108.9(4) . . ?
C25 C23 C20 110.3(4) . . ?
C25 C23 C24 109.4(5) . . ?
C25 C23 C26 108.7(4) . . ?
C26 C23 C20 110.0(4) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C1 N1 C4 111.1(4) . . ?
C1 N1 C5 127.3(4) . . ?
C4 N1 C5 121.5(4) . . ?
C10 N2 C17 116.5(4) . . ?
C11 N2 C10 120.0(4) . . ?
C11 N2 C17 118.2(4) . . ?
N3 C27 C28 108.0(4) . . ?
O2 C27 C28 125.9(4) . . ?
O2 C27 N3 126.1(4) . . ?
C27 C28 H28 107.6 . . ?
C27 C28 C29 102.5(3) . . ?
C29 C28 H28 107.6 . . ?
C35 C28 C27 113.8(4) . . ?
C35 C28 H28 107.6 . . ?
C35 C28 C29 117.2(3) . . ?
C30 C29 C28 100.3(3) . . ?
C44 C29 C28 113.7(3) . . ?
C44 C29 C30 111.4(4) . . ?
C44 C29 C48 110.2(3) . . ?
C48 C29 C28 110.6(3) . . ?
C48 C29 C30 110.3(3) . . ?
C29 C30 H30A 110.8 . . ?
C29 C30 H30B 110.8 . . ?
H30A C30 H30B 108.9 . . ?
N3 C30 C29 104.8(3) . . ?
N3 C30 H30A 110.8 . . ?
N3 C30 H30B 110.8 . . ?
C32 C31 C33 114.9(6) . . ?
C32 C31 C34 103.5(5) . . ?
C32 C31 N3 111.2(5) . . ?
C33 C31 C34 106.9(5) . . ?
N3 C31 C33 109.0(4) . . ?
N3 C31 C34 111.2(4) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C31 C34 H34A 109.5 . . ?
C31 C34 H34B 109.5 . . ?
C31 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C28 C35 H35A 109.0 . . ?
C28 C35 H35B 109.0 . . ?
C28 C35 C36 112.8(4) . . ?
H35A C35 H35B 107.8 . . ?
C36 C35 H35A 109.0 . . ?
C36 C35 H35B 109.0 . . ?
C35 C36 H36A 108.8 . . ?
C35 C36 H36B 108.8 . . ?
H36A C36 H36B 107.7 . . ?
N4 C36 C35 113.9(4) . . ?
N4 C36 H36A 108.8 . . ?
N4 C36 H36B 108.8 . . ?
C38 C37 C42 115.3(5) . . ?
N4 C37 C38 122.3(5) . . ?
N4 C37 C42 122.4(5) . . ?
C37 C38 H38 118.9 . . ?
C39 C38 C37 122.2(6) . . ?
C39 C38 H38 118.9 . . ?
C38 C39 H39 119.4 . . ?
C40 C39 C38 121.2(6) . . ?
C40 C39 H39 119.4 . . ?
C39 C40 H40 121.2 . . ?
C39 C40 C41 117.7(6) . . ?
C41 C40 H40 121.2 . . ?
C40 C41 H41 119.0 . . ?
C42 C41 C40 121.9(5) . . ?
C42 C41 H41 119.0 . . ?
C37 C42 H42 119.2 . . ?
C41 C42 C37 121.7(5) . . ?
C41 C42 H42 119.2 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
N4 C43 H43A 109.5 . . ?
N4 C43 H43B 109.5 . . ?
N4 C43 H43C 109.5 . . ?
C29 C44 H44 117.7 . . ?
C45 C44 C29 124.7(4) . . ?
C45 C44 H44 117.7 . . ?
C44 C45 H45 116.8 . . ?
C44 C45 C46 126.4(4) . . ?
C46 C45 H45 116.8 . . ?
C45 C46 H46 106.4 . . ?
C45 C46 C47 109.6(4) . . ?
C45 C46 C49 113.8(4) . . ?
C47 C46 H46 106.4 . . ?
C47 C46 C49 113.6(4) . . ?
C49 C46 H46 106.4 . . ?
C46 C47 H47 117.8 . . ?
C48 C47 C46 124.4(4) . . ?
C48 C47 H47 117.8 . . ?
C29 C48 H48 117.7 . . ?
C47 C48 C29 124.7(4) . . ?
C47 C48 H48 117.7 . . ?
C50 C49 C46 107.8(4) . . ?
C51 C49 C46 110.3(4) . . ?
C51 C49 C50 109.6(4) . . ?
C52 C49 C46 110.6(4) . . ?
C52 C49 C50 109.5(4) . . ?
C52 C49 C51 109.0(5) . . ?
C49 C50 H50A 109.5 . . ?
C49 C50 H50B 109.5 . . ?
C49 C50 H50C 109.5 . . ?
H50A C50 H50B 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C49 C51 H51A 109.5 . . ?
C49 C51 H51B 109.5 . . ?
C49 C51 H51C 109.5 . . ?
H51A C51 H51B 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C49 C52 H52A 109.5 . . ?
C49 C52 H52B 109.5 . . ?
C49 C52 H52C 109.5 . . ?
H52A C52 H52B 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C27 N3 C30 111.3(4) . . ?
C27 N3 C31 125.8(4) . . ?
C30 N3 C31 122.6(4) . . ?
C37 N4 C36 122.0(4) . . ?
C37 N4 C43 120.6(4) . . ?
C43 N4 C36 116.6(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 33.5(4) . . . . ?
C1 C2 C3 C18 -82.4(4) . . . . ?
C1 C2 C3 C22 151.9(4) . . . . ?
C1 C2 C9 C10 -81.3(5) . . . . ?
C2 C1 N1 C4 6.8(5) . . . . ?
C2 C1 N1 C5 -176.8(4) . . . . ?
C2 C3 C4 N1 -30.2(4) . . . . ?
C2 C3 C18 C19 -127.8(4) . . . . ?
C2 C3 C22 C21 128.0(5) . . . . ?
C2 C9 C10 N2 -179.3(4) . . . . ?
C3 C2 C9 C10 157.7(4) . . . . ?
C3 C4 N1 C1 15.7(5) . . . . ?
C3 C4 N1 C5 -160.9(4) . . . . ?
C3 C18 C19 C20 -0.9(7) . . . . ?
C4 C3 C18 C19 123.2(5) . . . . ?
C4 C3 C22 C21 -120.9(5) . . . . ?
C6 C5 N1 C1 -82.3(6) . . . . ?
C6 C5 N1 C4 93.8(5) . . . . ?
C7 C5 N1 C1 37.4(7) . . . . ?
C7 C5 N1 C4 -146.5(5) . . . . ?
C8 C5 N1 C1 155.0(5) . . . . ?
C8 C5 N1 C4 -29.0(6) . . . . ?
C9 C2 C3 C4 160.0(4) . . . . ?
C9 C2 C3 C18 44.1(5) . . . . ?
C9 C2 C3 C22 -81.5(5) . . . . ?
C9 C10 N2 C11 -77.6(5) . . . . ?
C9 C10 N2 C17 76.1(5) . . . . ?
C11 C12 C13 C14 0.8(9) . . . . ?
C12 C11 C16 C15 1.9(7) . . . . ?
C12 C11 N2 C10 170.3(4) . . . . ?
C12 C11 N2 C17 17.0(6) . . . . ?
C12 C13 C14 C15 -0.2(9) . . . . ?
C13 C14 C15 C16 0.5(8) . . . . ?
C14 C15 C16 C11 -1.4(8) . . . . ?
C16 C11 C12 C13 -1.6(7) . . . . ?
C16 C11 N2 C10 -11.1(6) . . . . ?
C16 C11 N2 C17 -164.3(4) . . . . ?
C18 C3 C4 N1 86.7(4) . . . . ?
C18 C3 C22 C21 2.0(6) . . . . ?
C18 C19 C20 C21 1.0(6) . . . . ?
C18 C19 C20 C23 129.7(5) . . . . ?
C19 C20 C21 C22 0.3(6) . . . . ?
C19 C20 C23 C24 -62.9(5) . . . . ?
C19 C20 C23 C25 57.6(5) . . . . ?
C19 C20 C23 C26 177.4(4) . . . . ?
C20 C21 C22 C3 -1.9(7) . . . . ?
C21 C20 C23 C24 64.2(5) . . . . ?
C21 C20 C23 C25 -175.3(4) . . . . ?
C21 C20 C23 C26 -55.4(5) . . . . ?
C22 C3 C4 N1 -150.0(4) . . . . ?
C22 C3 C18 C19 -0.6(6) . . . . ?
C23 C20 C21 C22 -129.1(5) . . . . ?
N1 C1 C2 C3 -26.7(4) . . . . ?
N1 C1 C2 C9 -154.4(3) . . . . ?
N2 C11 C12 C13 177.1(5) . . . . ?
N2 C11 C16 C15 -176.8(4) . . . . ?
O1 C1 C2 C3 152.7(4) . . . . ?
O1 C1 C2 C9 24.9(6) . . . . ?
O1 C1 N1 C4 -172.5(4) . . . . ?
O1 C1 N1 C5 3.9(7) . . . . ?
C27 C28 C29 C30 34.7(4) . . . . ?
C27 C28 C29 C44 153.7(4) . . . . ?
C27 C28 C29 C48 -81.7(4) . . . . ?
C27 C28 C35 C36 -77.7(5) . . . . ?
C28 C27 N3 C30 5.2(5) . . . . ?
C28 C27 N3 C31 -168.9(4) . . . . ?
C28 C29 C30 N3 -32.3(4) . . . . ?
C28 C29 C44 C45 126.3(5) . . . . ?
C28 C29 C48 C47 -126.0(5) . . . . ?
C28 C35 C36 N4 176.7(4) . . . . ?
C29 C28 C35 C36 162.9(4) . . . . ?
C29 C30 N3 C27 18.1(5) . . . . ?
C29 C30 N3 C31 -167.5(4) . . . . ?
C29 C44 C45 C46 -3.7(8) . . . . ?
C30 C29 C44 C45 -121.2(5) . . . . ?
C30 C29 C48 C47 124.0(5) . . . . ?
C32 C31 N3 C27 152.2(5) . . . . ?
C32 C31 N3 C30 -21.4(7) . . . . ?
C33 C31 N3 C27 -80.2(6) . . . . ?
C33 C31 N3 C30 106.3(6) . . . . ?
C34 C31 N3 C27 37.4(7) . . . . ?
C34 C31 N3 C30 -136.1(5) . . . . ?
C35 C28 C29 C30 159.9(4) . . . . ?
C35 C28 C29 C44 -81.0(5) . . . . ?
C35 C28 C29 C48 43.6(5) . . . . ?
C35 C36 N4 C37 -96.1(5) . . . . ?
C35 C36 N4 C43 93.8(6) . . . . ?
C37 C38 C39 C40 -3.6(10) . . . . ?
C38 C37 C42 C41 1.8(7) . . . . ?
C38 C37 N4 C36 -165.6(5) . . . . ?
C38 C37 N4 C43 4.1(8) . . . . ?
C38 C39 C40 C41 2.7(10) . . . . ?
C39 C40 C41 C42 0.3(9) . . . . ?
C40 C41 C42 C37 -2.7(8) . . . . ?
C42 C37 C38 C39 1.2(8) . . . . ?
C42 C37 N4 C36 13.1(7) . . . . ?
C42 C37 N4 C43 -177.2(5) . . . . ?
C44 C29 C30 N3 -153.1(4) . . . . ?
C44 C29 C48 C47 0.6(6) . . . . ?
C44 C45 C46 C47 3.1(7) . . . . ?
C44 C45 C46 C49 -125.3(5) . . . . ?
C45 C46 C47 C48 -0.9(6) . . . . ?
C45 C46 C49 C50 -61.4(5) . . . . ?
C45 C46 C49 C51 178.9(5) . . . . ?
C45 C46 C49 C52 58.2(6) . . . . ?
C46 C47 C48 C29 -0.8(7) . . . . ?
C47 C46 C49 C50 172.2(4) . . . . ?
C47 C46 C49 C51 52.6(6) . . . . ?
C47 C46 C49 C52 -68.1(5) . . . . ?
C48 C29 C30 N3 84.3(4) . . . . ?
C48 C29 C44 C45 1.6(6) . . . . ?
C49 C46 C47 C48 127.6(5) . . . . ?
N3 C27 C28 C29 -25.9(4) . . . . ?
N3 C27 C28 C35 -153.3(4) . . . . ?
N4 C37 C38 C39 -180.0(5) . . . . ?
N4 C37 C42 C41 -177.0(5) . . . . ?
O2 C27 C28 C29 153.0(5) . . . . ?
O2 C27 C28 C35 25.5(7) . . . . ?
O2 C27 N3 C30 -173.6(5) . . . . ?
O2 C27 N3 C31 12.2(8) . . . . ?


_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 1.100
_oxdiff_exptl_absorpt_empirical_full_min 0.924
####################################################################### 
# 
# 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_11890
_audit_block_doi                 10.5517/ccdc.csd.cc2d3dkh
_database_code_depnum_ccdc_archive 'CCDC 2207806'
loop_
_audit_author_name
_audit_author_address
'guohui zeng'
;South China University of Technology
China
;
_audit_update_record             
;
2022-09-16 deposited with the CCDC.	2024-04-03 downloaded from the CCDC.
;
_audit_creation_date             2022-09-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H33 N3 O'
_chemical_formula_sum            'C23 H33 N3 O'
_chemical_formula_weight         367.52
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.9111(8)
_cell_length_b                   17.4811(13)
_cell_length_c                   12.6792(13)
_cell_angle_alpha                90
_cell_angle_beta                 95.028(9)
_cell_angle_gamma                90
_cell_volume                     2188.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1568
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.4850
_cell_measurement_theta_min      2.3650
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.116
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.0734
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9602
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         1.989
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -3.00  75.00   1.00   12.50    --   15.49  38.00   0.00   78
  2  ω      9.00  44.00   1.00   12.50    --   15.49  57.00  60.00   35
  3  ω    -48.00  32.00   1.00   12.50    --   15.49 -57.00-150.00   80
  4  ω     36.00  86.00   1.00   12.50    --   15.49 178.00-180.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0630491000
_diffrn_orient_matrix_UB_12      -0.0194052000
_diffrn_orient_matrix_UB_13      0.0039624000
_diffrn_orient_matrix_UB_21      0.0284302000
_diffrn_orient_matrix_UB_22      0.0298145000
_diffrn_orient_matrix_UB_23      -0.0288505000
_diffrn_orient_matrix_UB_31      0.0192880000
_diffrn_orient_matrix_UB_32      0.0195008000
_diffrn_orient_matrix_UB_33      0.0480711000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2090
_reflns_number_total             3802
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3802
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1693
_refine_ls_R_factor_gt           0.0993
_refine_ls_restrained_S_all      1.034
_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)+(0.0969P)²+2.2890P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2205
_refine_ls_wR_factor_ref         0.2649
_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
2. Uiso/Uaniso restraints and constraints
Uanis(C20) = Uanis(C23)
Uanis(C22) = Uanis(C21)
3.a Ternary CH refined with riding coordinates:
 C1(H1)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C18(H18A,H18B)
3.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C19(H19), C9(H9), C13(H13), C11(H11)
3.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C14(H14A,H14B,H14C), C21(H21A,H21B,H21C), C15(H15A,H15B,
 H15C), C23(H23A,H23B,H23C), C22(H22A,H22B,H22C)
;
_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 0.3746(3) 0.69234(18) 0.5177(3) 0.0651(9) Uani 1 1 d . . . . .
N1 N 0.3838(3) 0.6392(2) 0.6851(3) 0.0533(10) Uani 1 1 d . . . . .
N2 N 0.7671(4) 0.7119(2) 0.3677(3) 0.0570(10) Uani 1 1 d . . . . .
C4 C 0.4368(4) 0.6652(2) 0.5970(4) 0.0472(11) Uani 1 1 d . . . . .
C8 C 0.7348(5) 0.6702(2) 0.2757(3) 0.0484(11) Uani 1 1 d . . . . .
N3 N 0.8394(4) 0.5491(3) 0.7615(4) 0.0731(12) Uani 1 1 d . . . . .
C1 C 0.5881(4) 0.6555(2) 0.6126(3) 0.0426(10) Uani 1 1 d . . . . .
H1 H 0.6249 0.7020 0.6474 0.051 Uiso 1 1 calc R U . . .
C2 C 0.6067(4) 0.5899(2) 0.6949(3) 0.0406(10) Uani 1 1 d . . . . .
C3 C 0.4861(4) 0.6063(3) 0.7611(3) 0.0531(11) Uani 1 1 d . . . . .
H3A H 0.4535 0.5596 0.7913 0.064 Uiso 1 1 calc R U . . .
H3B H 0.5117 0.6421 0.8178 0.064 Uiso 1 1 calc R U . . .
C16 C 0.5908(4) 0.5131(2) 0.6435(3) 0.0479(11) Uani 1 1 d . . . . .
H16 H 0.5072 0.4999 0.6093 0.057 Uiso 1 1 calc R U . . .
C5 C 0.6611(4) 0.6445(2) 0.5127(3) 0.0458(10) Uani 1 1 d . . . . .
H5A H 0.7517 0.6255 0.5328 0.055 Uiso 1 1 calc R U . . .
H5B H 0.6136 0.6059 0.4689 0.055 Uiso 1 1 calc R U . . .
C6 C 0.6716(5) 0.7168(2) 0.4477(4) 0.0546(12) Uani 1 1 d . . . . .
H6A H 0.5828 0.7287 0.4133 0.065 Uiso 1 1 calc R U . . .
H6B H 0.6981 0.7588 0.4951 0.065 Uiso 1 1 calc R U . . .
C17 C 0.6895(5) 0.4643(3) 0.6447(4) 0.0611(13) Uani 1 1 d . . . . .
H17 H 0.6744 0.4176 0.6106 0.073 Uiso 1 1 calc R U . . .
C19 C 0.7403(5) 0.5949(3) 0.7592(3) 0.0562(12) Uani 1 1 d . . . . .
H19 H 0.7521 0.6373 0.8033 0.067 Uiso 1 1 calc R U . . .
C9 C 0.6016(5) 0.6538(2) 0.2380(4) 0.0584(12) Uani 1 1 d . . . . .
H9 H 0.5319 0.6677 0.2787 0.070 Uiso 1 1 calc R U . . .
C10 C 0.5694(7) 0.6175(3) 0.1416(4) 0.0747(16) Uani 1 1 d . . . . .
C13 C 0.8365(5) 0.6457(3) 0.2138(4) 0.0649(13) Uani 1 1 d . . . . .
H13 H 0.9263 0.6550 0.2378 0.078 Uiso 1 1 calc R U . . .
C20 C 0.2382(6) 0.6412(4) 0.7034(6) 0.0982(15) Uani 1 1 d . . . . .
C11 C 0.6757(9) 0.5941(3) 0.0836(4) 0.088(2) Uani 1 1 d . . . . .
H11 H 0.6562 0.5684 0.0198 0.106 Uiso 1 1 calc R U . . .
C7 C 0.9076(5) 0.7172(3) 0.4082(4) 0.0853(17) Uani 1 1 d . . . . .
H7A H 0.9447 0.6667 0.4179 0.128 Uiso 1 1 calc R U . . .
H7B H 0.9143 0.7437 0.4748 0.128 Uiso 1 1 calc R U . . .
H7C H 0.9572 0.7448 0.3587 0.128 Uiso 1 1 calc R U . . .
C12 C 0.8095(7) 0.6083(3) 0.1191(4) 0.0820(17) Uani 1 1 d . . . . .
C18 C 0.8247(5) 0.4801(3) 0.6983(5) 0.0915(19) Uani 1 1 d . . . . .
H18A H 0.8505 0.4370 0.7439 0.110 Uiso 1 1 calc R U . . .
H18B H 0.8888 0.4826 0.6448 0.110 Uiso 1 1 calc R U . . .
C14 C 0.4248(7) 0.6056(4) 0.1008(5) 0.108(2) Uani 1 1 d . . . . .
H14A H 0.4142 0.5554 0.0705 0.162 Uiso 1 1 calc R U . . .
H14B H 0.3991 0.6433 0.0477 0.162 Uiso 1 1 calc R U . . .
H14C H 0.3680 0.6104 0.1581 0.162 Uiso 1 1 calc R U . . .
C21 C 0.2152(7) 0.6201(5) 0.8151(6) 0.149(2) Uani 1 1 d . . . . .
H21A H 0.2415 0.5678 0.8280 0.224 Uiso 1 1 calc R U . . .
H21B H 0.1211 0.6261 0.8255 0.224 Uiso 1 1 calc R U . . .
H21C H 0.2684 0.6528 0.8632 0.224 Uiso 1 1 calc R U . . .
C15 C 0.9236(8) 0.5808(5) 0.0558(5) 0.132(3) Uani 1 1 d . . . . .
H15A H 0.9827 0.6229 0.0439 0.198 Uiso 1 1 calc R U . . .
H15B H 0.8863 0.5608 -0.0110 0.198 Uiso 1 1 calc R U . . .
H15C H 0.9739 0.5414 0.0946 0.198 Uiso 1 1 calc R U . . .
C23 C 0.1770(6) 0.7166(4) 0.6765(5) 0.0982(15) Uani 1 1 d . . . . .
H23A H 0.2160 0.7545 0.7249 0.147 Uiso 1 1 calc R U . . .
H23B H 0.0810 0.7142 0.6817 0.147 Uiso 1 1 calc R U . . .
H23C H 0.1943 0.7302 0.6056 0.147 Uiso 1 1 calc R U . . .
C22 C 0.1651(7) 0.5814(6) 0.6298(7) 0.149(2) Uani 1 1 d . . . . .
H22A H 0.1854 0.5906 0.5583 0.224 Uiso 1 1 calc R U . . .
H22B H 0.0691 0.5854 0.6341 0.224 Uiso 1 1 calc R U . . .
H22C H 0.1950 0.5311 0.6511 0.224 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C4 1.228(5) . ?
N1 C4 1.354(5) . ?
N1 C3 1.454(5) . ?
N1 C20 1.482(6) . ?
N2 C8 1.389(6) . ?
N2 C6 1.449(6) . ?
N2 C7 1.444(6) . ?
C4 C1 1.505(6) . ?
C8 C9 1.394(6) . ?
C8 C13 1.399(6) . ?
N3 C19 1.266(5) . ?
N3 C18 1.448(6) . ?
C1 H1 0.9800 . ?
C1 C2 1.551(5) . ?
C1 C5 1.526(5) . ?
C2 C3 1.547(5) . ?
C2 C16 1.493(5) . ?
C2 C19 1.495(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C16 H16 0.9300 . ?
C16 C17 1.297(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.518(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C17 H17 0.9300 . ?
C17 C18 1.475(7) . ?
C19 H19 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.389(7) . ?
C10 C11 1.398(8) . ?
C10 C14 1.495(8) . ?
C13 H13 0.9300 . ?
C13 C12 1.372(7) . ?
C20 C21 1.499(9) . ?
C20 C23 1.479(8) . ?
C20 C22 1.539(10) . ?
C11 H11 0.9300 . ?
C11 C12 1.385(8) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C12 C15 1.520(8) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
C4 N1 C3 112.4(3) . . ?
C4 N1 C20 125.1(4) . . ?
C3 N1 C20 122.5(4) . . ?
C8 N2 C6 120.1(4) . . ?
C8 N2 C7 118.4(4) . . ?
C7 N2 C6 114.6(4) . . ?
O1 C4 N1 127.1(4) . . ?
O1 C4 C1 125.0(4) . . ?
N1 C4 C1 107.9(4) . . ?
N2 C8 C9 122.6(4) . . ?
N2 C8 C13 120.5(4) . . ?
C9 C8 C13 116.8(4) . . ?
C19 N3 C18 118.3(4) . . ?
C4 C1 H1 107.1 . . ?
C4 C1 C2 103.3(3) . . ?
C4 C1 C5 116.4(4) . . ?
C2 C1 H1 107.1 . . ?
C5 C1 H1 107.1 . . ?
C5 C1 C2 115.3(3) . . ?
C3 C2 C1 100.1(3) . . ?
C16 C2 C1 111.7(3) . . ?
C16 C2 C3 110.3(3) . . ?
C16 C2 C19 110.2(4) . . ?
C19 C2 C1 111.7(3) . . ?
C19 C2 C3 112.5(3) . . ?
N1 C3 C2 103.9(3) . . ?
N1 C3 H3A 111.0 . . ?
N1 C3 H3B 111.0 . . ?
C2 C3 H3A 111.0 . . ?
C2 C3 H3B 111.0 . . ?
H3A C3 H3B 109.0 . . ?
C2 C16 H16 118.8 . . ?
C17 C16 C2 122.4(4) . . ?
C17 C16 H16 118.8 . . ?
C1 C5 H5A 108.8 . . ?
C1 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
C6 C5 C1 113.9(3) . . ?
C6 C5 H5A 108.8 . . ?
C6 C5 H5B 108.8 . . ?
N2 C6 C5 114.3(3) . . ?
N2 C6 H6A 108.7 . . ?
N2 C6 H6B 108.7 . . ?
C5 C6 H6A 108.7 . . ?
C5 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
C16 C17 H17 118.8 . . ?
C16 C17 C18 122.4(4) . . ?
C18 C17 H17 118.8 . . ?
N3 C19 C2 128.6(4) . . ?
N3 C19 H19 115.7 . . ?
C2 C19 H19 115.7 . . ?
C8 C9 H9 118.9 . . ?
C10 C9 C8 122.3(5) . . ?
C10 C9 H9 118.9 . . ?
C9 C10 C11 118.1(5) . . ?
C9 C10 C14 120.5(6) . . ?
C11 C10 C14 121.4(6) . . ?
C8 C13 H13 118.6 . . ?
C12 C13 C8 122.9(5) . . ?
C12 C13 H13 118.6 . . ?
N1 C20 C21 111.9(5) . . ?
N1 C20 C22 107.6(5) . . ?
C21 C20 C22 107.7(6) . . ?
C23 C20 N1 111.7(5) . . ?
C23 C20 C21 110.1(6) . . ?
C23 C20 C22 107.7(6) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.4(5) . . ?
C12 C11 H11 119.3 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C12 C11 118.5(6) . . ?
C13 C12 C15 121.0(6) . . ?
C11 C12 C15 120.5(6) . . ?
N3 C18 C17 117.0(4) . . ?
N3 C18 H18A 108.1 . . ?
N3 C18 H18B 108.1 . . ?
C17 C18 H18A 108.1 . . ?
C17 C18 H18B 108.1 . . ?
H18A C18 H18B 107.3 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C4 C1 C2 -155.7(4) . . . . ?
O1 C4 C1 C5 -28.2(6) . . . . ?
N1 C4 C1 C2 24.5(4) . . . . ?
N1 C4 C1 C5 152.0(3) . . . . ?
N2 C8 C9 C10 174.7(4) . . . . ?
N2 C8 C13 C12 -176.0(4) . . . . ?
C4 N1 C3 C2 -18.4(4) . . . . ?
C4 N1 C20 C21 -170.6(6) . . . . ?
C4 N1 C20 C23 -46.7(8) . . . . ?
C4 N1 C20 C22 71.3(7) . . . . ?
C4 C1 C2 C3 -33.5(4) . . . . ?
C4 C1 C2 C16 83.2(4) . . . . ?
C4 C1 C2 C19 -152.8(3) . . . . ?
C4 C1 C5 C6 73.6(5) . . . . ?
C8 N2 C6 C5 74.7(5) . . . . ?
C8 C9 C10 C11 2.8(6) . . . . ?
C8 C9 C10 C14 -176.0(4) . . . . ?
C8 C13 C12 C11 -0.3(7) . . . . ?
C8 C13 C12 C15 -178.4(5) . . . . ?
C1 C2 C3 N1 31.4(4) . . . . ?
C1 C2 C16 C17 115.9(5) . . . . ?
C1 C2 C19 N3 -114.3(5) . . . . ?
C1 C5 C6 N2 166.0(4) . . . . ?
C2 C1 C5 C6 -165.1(3) . . . . ?
C2 C16 C17 C18 0.9(7) . . . . ?
C3 N1 C4 O1 176.3(4) . . . . ?
C3 N1 C4 C1 -3.9(5) . . . . ?
C3 N1 C20 C21 11.1(8) . . . . ?
C3 N1 C20 C23 135.0(5) . . . . ?
C3 N1 C20 C22 -107.0(6) . . . . ?
C3 C2 C16 C17 -133.7(4) . . . . ?
C3 C2 C19 N3 134.0(5) . . . . ?
C16 C2 C3 N1 -86.3(4) . . . . ?
C16 C2 C19 N3 10.4(7) . . . . ?
C16 C17 C18 N3 7.5(8) . . . . ?
C5 C1 C2 C3 -161.7(3) . . . . ?
C5 C1 C2 C16 -45.0(5) . . . . ?
C5 C1 C2 C19 79.0(4) . . . . ?
C6 N2 C8 C9 22.2(6) . . . . ?
C6 N2 C8 C13 -160.7(4) . . . . ?
C19 N3 C18 C17 -6.4(8) . . . . ?
C19 C2 C3 N1 150.2(4) . . . . ?
C19 C2 C16 C17 -8.9(6) . . . . ?
C9 C8 C13 C12 1.2(6) . . . . ?
C9 C10 C11 C12 -1.8(7) . . . . ?
C10 C11 C12 C13 0.6(8) . . . . ?
C10 C11 C12 C15 178.7(5) . . . . ?
C13 C8 C9 C10 -2.4(6) . . . . ?
C20 N1 C4 O1 -2.2(7) . . . . ?
C20 N1 C4 C1 177.6(4) . . . . ?
C20 N1 C3 C2 160.0(4) . . . . ?
C7 N2 C8 C9 171.8(4) . . . . ?
C7 N2 C8 C13 -11.2(6) . . . . ?
C7 N2 C6 C5 -76.0(5) . . . . ?
C18 N3 C19 C2 -2.9(8) . . . . ?
C14 C10 C11 C12 177.0(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 1.129
_oxdiff_exptl_absorpt_empirical_full_min 0.868
