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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_201803167
_database_code_depnum_ccdc_archive 'CCDC 1917780'
loop_
_audit_author_name
_audit_author_address
'Yong You'
;Cheng Du University
China
;
_audit_update_record             
;
2019-05-22 deposited with the CCDC.	2019-06-25 downloaded from the CCDC.
;
_audit_creation_date             2018-03-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H25 N3 O4'
_chemical_formula_sum            'C28 H25 N3 O4'
_chemical_formula_weight         467.51
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C22H20N2O8
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   8.0685(2)
_cell_length_b                   18.8284(6)
_cell_length_c                   8.1393(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.576(2)
_cell_angle_gamma                90
_cell_volume                     1230.64(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5378
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6080
_cell_measurement_theta_min      4.6770
_shelx_estimated_absorpt_T_max   0.903
_shelx_estimated_absorpt_T_min   0.874
_exptl_absorpt_coefficient_mu    0.694
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87065
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10206
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         4.697
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -62.00   36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   77.0000   30.0000 98

#__ type_ start__ end____ width___ exp.time_
  2 omega -102.00  -15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000  -90.0000 87

#__ type_ start__ end____ width___ exp.time_
  3 omega  -52.00  -24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000 -180.0000 28

#__ type_ start__ end____ width___ exp.time_
  4 omega  -91.00  -56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000 -180.0000 35

#__ type_ start__ end____ width___ exp.time_
  5 omega   16.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   90.0000 61

#__ type_ start__ end____ width___ exp.time_
  6 omega   33.00   64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000 -120.0000 31

#__ type_ start__ end____ width___ exp.time_
  7 omega  -14.00   12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
  8 omega  -29.00    3.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000 -180.0000 32

#__ type_ start__ end____ width___ exp.time_
  9 omega  -32.00    3.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000 -180.0000 35

#__ type_ start__ end____ width___ exp.time_
 10 omega   28.00   58.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000   60.0000 30

#__ type_ start__ end____ width___ exp.time_
 11 omega    8.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
 12 omega   63.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   90.0000 37

#__ type_ start__ end____ width___ exp.time_
 13 omega   54.00   80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 14 omega   23.00   49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 15 omega    7.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000 -180.0000 53

#__ type_ start__ end____ width___ exp.time_
 16 omega  -32.00   16.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000   60.0000 48

#__ type_ start__ end____ width___ exp.time_
 17 omega   73.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 18 omega   18.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000 -180.0000 51

#__ type_ start__ end____ width___ exp.time_
 19 omega   76.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000 -180.0000 28

#__ type_ start__ end____ width___ exp.time_
 20 omega   93.00  146.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  -30.0000 53

#__ type_ start__ end____ width___ exp.time_
 21 omega   83.00  114.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 31

#__ type_ start__ end____ width___ exp.time_
 22 omega   43.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 55

#__ type_ start__ end____ width___ exp.time_
 23 omega   42.00   68.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 24 omega   44.00   70.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 25 omega   39.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 51

#__ type_ start__ end____ width___ exp.time_
 26 omega   39.00   74.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 35

#__ type_ start__ end____ width___ exp.time_
 27 omega   90.00  175.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -120.0000 85

#__ type_ start__ end____ width___ exp.time_
 28 omega   56.00  127.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -60.0000 71

#__ type_ start__ end____ width___ exp.time_
 29 omega   38.00   91.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 53

#__ type_ start__ end____ width___ exp.time_
 30 omega   40.00  100.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 60

#__ type_ start__ end____ width___ exp.time_
 31 omega   38.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 52

#__ type_ start__ end____ width___ exp.time_
 32 omega   93.00  175.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  120.0000 82

#__ type_ start__ end____ width___ exp.time_
 33 omega   60.00  106.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -30.0000 46

#__ type_ start__ end____ width___ exp.time_
 34 omega   40.00   70.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 30

#__ type_ start__ end____ width___ exp.time_
 35 omega   49.00  125.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   90.0000 76

#__ type_ start__ end____ width___ exp.time_
 36 omega   79.00  150.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000 -120.0000 71

#__ type_ start__ end____ width___ exp.time_
 37 omega   67.00   93.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 38 omega  113.00  145.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   30.0000 32

#__ type_ start__ end____ width___ exp.time_
 39 omega   44.00   74.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 30

#__ type_ start__ end____ width___ exp.time_
 40 omega  112.00  138.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 41 omega  152.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 42 omega  141.00  173.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -90.0000 32

#__ type_ start__ end____ width___ exp.time_
 43 omega   44.00   70.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 44 omega   57.00   83.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 45 omega  100.00  116.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000 -150.0000 16
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0858620000
_diffrn_orient_matrix_UB_12      0.0693271000
_diffrn_orient_matrix_UB_13      -0.0458920000
_diffrn_orient_matrix_UB_21      0.1623502000
_diffrn_orient_matrix_UB_22      -0.0412871000
_diffrn_orient_matrix_UB_23      -0.0166846000
_diffrn_orient_matrix_UB_31      -0.0554473000
_diffrn_orient_matrix_UB_32      -0.0136153000
_diffrn_orient_matrix_UB_33      -0.1837719000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.935
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                4196
_reflns_number_total             4407
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 
;
 Flack x determined using 1912 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(10)
_refine_ls_extinction_coef       0.0069(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         4407
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0345
_refine_ls_restrained_S_all      1.031
_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)+(0.0509P)²+0.1102P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0924
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C25-C27
 1.55 with sigma of 0.02
 C25-C26A
 1.55 with sigma of 0.02
 C27A-C25
 1.55 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C28) = Uanis(C28A)
Uanis(C27) = Uanis(C27A)
Uanis(C26) = Uanis(C26A)
4. Others
 Sof(C26A)=Sof(H26D)=Sof(H26E)=Sof(H26F)=Sof(C27A)=Sof(H27D)=Sof(H27E)=
 Sof(H27F)=Sof(C28A)=Sof(H28D)=Sof(H28E)=Sof(H28F)=1-FVAR(1)
 Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(H26C)=Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(H27C)=
 Sof(C28)=Sof(H28A)=Sof(H28B)=Sof(H28C)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C14(H14), C15(H15), C16(H16),
 C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
5.b Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C26A(H26D,H26E,H26F), C27(H27A,H27B,H27C), C27A(H27D,
 H27E,H27F), C28(H28A,H28B,H28C), C28A(H28D,H28E,H28F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.3310(3) 0.67816(15) 0.7032(3) 0.0397(5) Uani 1 1 d . . . . .
C2 C 0.2521(3) 0.73191(14) 0.8163(3) 0.0386(5) Uani 1 1 d . . . . .
C3 C 0.3620(3) 0.79699(14) 0.8451(3) 0.0406(5) Uani 1 1 d . . . . .
C4 C 0.5336(3) 0.79042(15) 0.8406(3) 0.0428(5) Uani 1 1 d . . . . .
C5 C 0.6103(3) 0.72162(15) 0.8058(3) 0.0440(6) Uani 1 1 d . . . . .
C6 C 0.6354(3) 0.84981(17) 0.8697(4) 0.0551(7) Uani 1 1 d . . . . .
H6 H 0.7498 0.8455 0.8660 0.066 Uiso 1 1 calc R . . . .
C7 C 0.5686(4) 0.91451(17) 0.9035(4) 0.0637(8) Uani 1 1 d . . . . .
H7 H 0.6369 0.9541 0.9210 0.076 Uiso 1 1 calc R . . . .
C8 C 0.3985(4) 0.92023(18) 0.9113(5) 0.0653(8) Uani 1 1 d . . . . .
H8 H 0.3526 0.9639 0.9350 0.078 Uiso 1 1 calc R . . . .
C9 C 0.2968(3) 0.86193(17) 0.8844(4) 0.0545(7) Uani 1 1 d . . . . .
H9 H 0.1831 0.8663 0.8926 0.065 Uiso 1 1 calc R . . . .
C10 C 0.3053(3) 0.71547(16) 1.1286(3) 0.0488(6) Uani 1 1 d . . . . .
H10 H 0.3634 0.7578 1.1482 0.059 Uiso 1 1 calc R . . . .
C11 C 0.2380(3) 0.69302(13) 0.9787(3) 0.0372(5) Uani 1 1 d . . . . .
C12 C 0.1575(3) 0.62638(14) 1.0044(3) 0.0400(5) Uani 1 1 d . . . . .
C13 C 0.1845(3) 0.61241(15) 1.1751(3) 0.0454(6) Uani 1 1 d . . . . .
C14 C 0.1241(4) 0.55238(18) 1.2477(4) 0.0585(7) Uani 1 1 d . . . . .
H14 H 0.1444 0.5443 1.3605 0.070 Uiso 1 1 calc R . . . .
C15 C 0.0338(4) 0.50563(18) 1.1472(4) 0.0640(8) Uani 1 1 d . . . . .
H15 H -0.0085 0.4648 1.1923 0.077 Uiso 1 1 calc R . . . .
C16 C 0.0035(4) 0.51809(18) 0.9770(4) 0.0638(8) Uani 1 1 d . . . . .
H16 H -0.0593 0.4855 0.9117 0.077 Uiso 1 1 calc R . . . .
C17 C 0.0643(3) 0.57732(17) 0.9045(4) 0.0514(6) Uani 1 1 d . . . . .
H17 H 0.0440 0.5847 0.7913 0.062 Uiso 1 1 calc R . . . .
C18 C 0.5731(3) 0.60646(16) 0.6636(3) 0.0492(6) Uani 1 1 d . . . . .
C19 C 0.5360(5) 0.54226(19) 0.7280(5) 0.0720(9) Uani 1 1 d . . . . .
H19 H 0.4714 0.5396 0.8164 0.086 Uiso 1 1 calc R . . . .
C20 C 0.5955(6) 0.4812(2) 0.6605(7) 0.0937(13) Uani 1 1 d . . . . .
H20 H 0.5714 0.4374 0.7050 0.112 Uiso 1 1 calc R . . . .
C21 C 0.6872(6) 0.4839(3) 0.5322(7) 0.0998(16) Uani 1 1 d . . . . .
H21 H 0.7225 0.4424 0.4848 0.120 Uiso 1 1 calc R . . . .
C22 C 0.7280(7) 0.5482(3) 0.4724(7) 0.121(2) Uani 1 1 d . . . . .
H22 H 0.7936 0.5504 0.3846 0.145 Uiso 1 1 calc R . . . .
C23 C 0.6733(6) 0.6112(2) 0.5402(6) 0.0919(14) Uani 1 1 d . . . . .
H23 H 0.7050 0.6551 0.5016 0.110 Uiso 1 1 calc R . . . .
C24 C 0.0688(3) 0.77877(15) 0.5873(3) 0.0467(6) Uani 1 1 d . . . . .
C25 C -0.1521(4) 0.81792(19) 0.3784(4) 0.0639(8) Uani 1 1 d D . . . .
C26 C -0.338(2) 0.8146(16) 0.392(2) 0.083(4) Uani 0.609(9) 1 d . . P A 1
H26A H -0.3689 0.7670 0.4196 0.125 Uiso 0.609(9) 1 calc GR . P A 1
H26B H -0.3974 0.8281 0.2890 0.125 Uiso 0.609(9) 1 calc GR . P A 1
H26C H -0.3666 0.8465 0.4773 0.125 Uiso 0.609(9) 1 calc GR . P A 1
C26A C -0.338(3) 0.806(3) 0.346(4) 0.083(4) Uani 0.391(9) 1 d D . P A 2
H26D H -0.3582 0.7577 0.3099 0.125 Uiso 0.391(9) 1 calc GR . P A 2
H26E H -0.3837 0.8379 0.2622 0.125 Uiso 0.391(9) 1 calc GR . P A 2
H26F H -0.3895 0.8137 0.4459 0.125 Uiso 0.391(9) 1 calc GR . P A 2
C27 C -0.100(4) 0.8917(9) 0.357(2) 0.124(7) Uani 0.609(9) 1 d D . P A 1
H27A H -0.1474 0.9214 0.4360 0.186 Uiso 0.609(9) 1 calc GR . P A 1
H27B H -0.1371 0.9074 0.2474 0.186 Uiso 0.609(9) 1 calc GR . P A 1
H27C H 0.0195 0.8946 0.3736 0.186 Uiso 0.609(9) 1 calc GR . P A 1
C27A C -0.120(7) 0.8959(14) 0.422(4) 0.124(7) Uani 0.391(9) 1 d D . P A 2
H27D H -0.1706 0.9075 0.5202 0.186 Uiso 0.391(9) 1 calc GR . P A 2
H27E H -0.1659 0.9253 0.3326 0.186 Uiso 0.391(9) 1 calc GR . P A 2
H27F H -0.0017 0.9040 0.4402 0.186 Uiso 0.391(9) 1 calc GR . P A 2
C28 C -0.1139(11) 0.7601(6) 0.2519(8) 0.091(2) Uani 0.609(9) 1 d . . P A 1
H28A H 0.0019 0.7621 0.2339 0.137 Uiso 0.609(9) 1 calc GR . P A 1
H28B H -0.1807 0.7683 0.1495 0.137 Uiso 0.609(9) 1 calc GR . P A 1
H28C H -0.1392 0.7141 0.2940 0.137 Uiso 0.609(9) 1 calc GR . P A 1
C28A C -0.0496(17) 0.8049(10) 0.2326(14) 0.091(2) Uani 0.391(9) 1 d . . P A 2
H28D H 0.0418 0.8377 0.2378 0.137 Uiso 0.391(9) 1 calc GR . P A 2
H28E H -0.1188 0.8116 0.1311 0.137 Uiso 0.391(9) 1 calc GR . P A 2
H28F H -0.0075 0.7572 0.2376 0.137 Uiso 0.391(9) 1 calc GR . P A 2
N1 N 0.5033(2) 0.67036(12) 0.7291(3) 0.0433(5) Uani 1 1 d . . . . .
N2 N 0.0874(2) 0.75085(13) 0.7416(3) 0.0434(5) Uani 1 1 d . . . . .
H2 H 0.002(4) 0.7355(16) 0.786(4) 0.046(8) Uiso 1 1 d . . . . .
N3 N 0.2757(3) 0.66728(15) 1.2461(3) 0.0555(6) Uani 1 1 d . . . . .
H3 H 0.285(5) 0.672(2) 1.344(5) 0.073(11) Uiso 1 1 d . . . . .
O1 O 0.2482(2) 0.64122(12) 0.6071(2) 0.0529(5) Uani 1 1 d . . . . .
O2 O 0.7564(2) 0.70932(13) 0.8363(3) 0.0631(6) Uani 1 1 d . . . . .
O3 O 0.1839(2) 0.79522(14) 0.5105(2) 0.0644(6) Uani 1 1 d . . . . .
O4 O -0.0934(2) 0.78578(12) 0.5378(3) 0.0595(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.546(3) . ?
C1 N1 1.394(3) . ?
C1 O1 1.200(3) . ?
C2 C3 1.518(4) . ?
C2 C11 1.525(3) . ?
C2 N2 1.451(3) . ?
C3 C4 1.394(3) . ?
C3 C9 1.381(4) . ?
C4 C5 1.475(4) . ?
C4 C6 1.394(4) . ?
C5 N1 1.401(4) . ?
C5 O2 1.204(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.371(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.384(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.375(5) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11 1.354(3) . ?
C10 N3 1.356(4) . ?
C11 C12 1.438(3) . ?
C12 C13 1.411(3) . ?
C12 C17 1.400(4) . ?
C13 C14 1.385(4) . ?
C13 N3 1.364(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.363(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.403(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.374(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.362(4) . ?
C18 C23 1.352(5) . ?
C18 N1 1.452(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.380(6) . ?
C20 H20 0.9300 . ?
C20 C21 1.338(7) . ?
C21 H21 0.9300 . ?
C21 C22 1.357(9) . ?
C22 H22 0.9300 . ?
C22 C23 1.397(6) . ?
C23 H23 0.9300 . ?
C24 N2 1.357(3) . ?
C24 O3 1.209(3) . ?
C24 O4 1.338(3) . ?
C25 C26 1.520(19) . ?
C25 C26A 1.51(3) . ?
C25 C27 1.467(15) . ?
C25 C27A 1.53(3) . ?
C25 C28 1.549(9) . ?
C25 C28A 1.530(13) . ?
C25 O4 1.468(3) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C26A H26D 0.9600 . ?
C26A H26E 0.9600 . ?
C26A H26F 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C27A H27D 0.9600 . ?
C27A H27E 0.9600 . ?
C27A H27F 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C28A H28D 0.9600 . ?
C28A H28E 0.9600 . ?
C28A H28F 0.9600 . ?
N2 H2 0.86(3) . ?
N3 H3 0.80(4) . ?

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 116.2(2) . . ?
O1 C1 C2 122.2(2) . . ?
O1 C1 N1 121.4(2) . . ?
C3 C2 C1 110.64(19) . . ?
C3 C2 C11 110.20(19) . . ?
C11 C2 C1 105.7(2) . . ?
N2 C2 C1 108.97(19) . . ?
N2 C2 C3 111.4(2) . . ?
N2 C2 C11 109.77(19) . . ?
C4 C3 C2 119.4(2) . . ?
C9 C3 C2 121.4(2) . . ?
C9 C3 C4 119.1(2) . . ?
C3 C4 C5 121.3(2) . . ?
C6 C4 C3 119.7(3) . . ?
C6 C4 C5 119.1(2) . . ?
N1 C5 C4 116.1(2) . . ?
O2 C5 C4 123.4(2) . . ?
O2 C5 N1 120.5(3) . . ?
C4 C6 H6 119.7 . . ?
C7 C6 C4 120.7(3) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 H7 120.4 . . ?
C6 C7 C8 119.3(3) . . ?
C8 C7 H7 120.4 . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.6(3) . . ?
C9 C8 H8 119.7 . . ?
C3 C9 H9 119.7 . . ?
C8 C9 C3 120.6(3) . . ?
C8 C9 H9 119.7 . . ?
C11 C10 H10 124.9 . . ?
C11 C10 N3 110.1(2) . . ?
N3 C10 H10 124.9 . . ?
C10 C11 C2 125.0(2) . . ?
C10 C11 C12 106.8(2) . . ?
C12 C11 C2 128.2(2) . . ?
C13 C12 C11 106.1(2) . . ?
C17 C12 C11 135.7(2) . . ?
C17 C12 C13 118.2(2) . . ?
C14 C13 C12 123.0(3) . . ?
N3 C13 C12 107.6(2) . . ?
N3 C13 C14 129.4(3) . . ?
C13 C14 H14 121.3 . . ?
C15 C14 C13 117.5(3) . . ?
C15 C14 H14 121.3 . . ?
C14 C15 H15 119.5 . . ?
C14 C15 C16 121.0(3) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 H16 119.2 . . ?
C17 C16 C15 121.7(3) . . ?
C17 C16 H16 119.2 . . ?
C12 C17 H17 120.7 . . ?
C16 C17 C12 118.6(3) . . ?
C16 C17 H17 120.7 . . ?
C19 C18 N1 119.1(3) . . ?
C23 C18 C19 120.9(3) . . ?
C23 C18 N1 120.0(3) . . ?
C18 C19 H19 120.4 . . ?
C18 C19 C20 119.2(4) . . ?
C20 C19 H19 120.4 . . ?
C19 C20 H20 119.4 . . ?
C21 C20 C19 121.3(5) . . ?
C21 C20 H20 119.4 . . ?
C20 C21 H21 120.5 . . ?
C20 C21 C22 119.1(4) . . ?
C22 C21 H21 120.5 . . ?
C21 C22 H22 119.4 . . ?
C21 C22 C23 121.1(5) . . ?
C23 C22 H22 119.4 . . ?
C18 C23 C22 118.2(4) . . ?
C18 C23 H23 120.9 . . ?
C22 C23 H23 120.9 . . ?
O3 C24 N2 123.8(2) . . ?
O3 C24 O4 126.7(2) . . ?
O4 C24 N2 109.5(2) . . ?
C26 C25 C28 106.4(9) . . ?
C26A C25 C27A 109(3) . . ?
C26A C25 C28A 116.2(13) . . ?
C27 C25 C26 110.3(18) . . ?
C27 C25 C28 120.6(11) . . ?
C27 C25 O4 115.0(7) . . ?
C27A C25 C28A 103.9(19) . . ?
O4 C25 C26 98.8(9) . . ?
O4 C25 C26A 108.6(16) . . ?
O4 C25 C27A 99.1(12) . . ?
O4 C25 C28 103.3(4) . . ?
O4 C25 C28A 117.8(5) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C26A H26D 109.5 . . ?
C25 C26A H26E 109.5 . . ?
C25 C26A H26F 109.5 . . ?
H26D C26A H26E 109.5 . . ?
H26D C26A H26F 109.5 . . ?
H26E C26A H26F 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C25 C27A H27D 109.5 . . ?
C25 C27A H27E 109.5 . . ?
C25 C27A H27F 109.5 . . ?
H27D C27A H27E 109.5 . . ?
H27D C27A H27F 109.5 . . ?
H27E C27A H27F 109.5 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C25 C28A H28D 109.5 . . ?
C25 C28A H28E 109.5 . . ?
C25 C28A H28F 109.5 . . ?
H28D C28A H28E 109.5 . . ?
H28D C28A H28F 109.5 . . ?
H28E C28A H28F 109.5 . . ?
C1 N1 C5 123.9(2) . . ?
C1 N1 C18 116.7(2) . . ?
C5 N1 C18 119.4(2) . . ?
C2 N2 H2 119(2) . . ?
C24 N2 C2 119.8(2) . . ?
C24 N2 H2 120(2) . . ?
C10 N3 C13 109.4(2) . . ?
C10 N3 H3 128(3) . . ?
C13 N3 H3 120(3) . . ?
C24 O4 C25 121.9(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O2 0.86(3) 2.12(3) 2.956(3) 164(3) 1_455
N3 H3 O1 0.80(4) 2.27(4) 3.008(3) 155(4) 1_556
N3 H3 O3 0.80(4) 2.84(4) 3.360(4) 124(4) 1_556

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 -28.8(3) . . . . ?
C1 C2 C3 C9 154.7(2) . . . . ?
C1 C2 C11 C10 123.3(3) . . . . ?
C1 C2 C11 C12 -54.9(3) . . . . ?
C1 C2 N2 C24 -57.2(3) . . . . ?
C2 C1 N1 C5 -21.9(3) . . . . ?
C2 C1 N1 C18 161.4(2) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C2 C3 C4 C6 -179.0(2) . . . . ?
C2 C3 C9 C8 179.5(3) . . . . ?
C2 C11 C12 C13 177.9(2) . . . . ?
C2 C11 C12 C17 -3.0(4) . . . . ?
C3 C2 C11 C10 3.7(3) . . . . ?
C3 C2 C11 C12 -174.5(2) . . . . ?
C3 C2 N2 C24 65.1(3) . . . . ?
C3 C4 C5 N1 19.1(3) . . . . ?
C3 C4 C5 O2 -162.8(2) . . . . ?
C3 C4 C6 C7 0.4(4) . . . . ?
C4 C3 C9 C8 2.9(4) . . . . ?
C4 C5 N1 C1 -7.8(3) . . . . ?
C4 C5 N1 C18 168.8(2) . . . . ?
C4 C6 C7 C8 1.1(5) . . . . ?
C5 C4 C6 C7 -179.6(3) . . . . ?
C6 C4 C5 N1 -161.0(2) . . . . ?
C6 C4 C5 O2 17.2(4) . . . . ?
C6 C7 C8 C9 -0.5(5) . . . . ?
C7 C8 C9 C3 -1.5(5) . . . . ?
C9 C3 C4 C5 177.6(2) . . . . ?
C9 C3 C4 C6 -2.3(4) . . . . ?
C10 C11 C12 C13 -0.6(3) . . . . ?
C10 C11 C12 C17 178.5(3) . . . . ?
C11 C2 C3 C4 87.8(2) . . . . ?
C11 C2 C3 C9 -88.8(3) . . . . ?
C11 C2 N2 C24 -172.6(2) . . . . ?
C11 C10 N3 C13 -1.2(3) . . . . ?
C11 C12 C13 C14 179.7(3) . . . . ?
C11 C12 C13 N3 -0.1(3) . . . . ?
C11 C12 C17 C16 -178.9(3) . . . . ?
C12 C13 C14 C15 -0.4(4) . . . . ?
C12 C13 N3 C10 0.8(3) . . . . ?
C13 C12 C17 C16 0.1(4) . . . . ?
C13 C14 C15 C16 0.0(5) . . . . ?
C14 C13 N3 C10 -179.0(3) . . . . ?
C14 C15 C16 C17 0.5(5) . . . . ?
C15 C16 C17 C12 -0.5(5) . . . . ?
C17 C12 C13 C14 0.4(4) . . . . ?
C17 C12 C13 N3 -179.4(2) . . . . ?
C18 C19 C20 C21 -0.7(7) . . . . ?
C19 C18 C23 C22 4.6(7) . . . . ?
C19 C18 N1 C1 -65.8(3) . . . . ?
C19 C18 N1 C5 117.3(3) . . . . ?
C19 C20 C21 C22 2.8(8) . . . . ?
C20 C21 C22 C23 -1.3(9) . . . . ?
C21 C22 C23 C18 -2.4(9) . . . . ?
C23 C18 C19 C20 -3.2(6) . . . . ?
C23 C18 N1 C1 114.2(4) . . . . ?
C23 C18 N1 C5 -62.7(4) . . . . ?
C26 C25 O4 C24 -177.8(10) . . . . ?
C26A C25 O4 C24 169.7(18) . . . . ?
C27 C25 O4 C24 -60.4(15) . . . . ?
C27A C25 O4 C24 -76(2) . . . . ?
C28 C25 O4 C24 72.9(5) . . . . ?
C28A C25 O4 C24 34.9(9) . . . . ?
N1 C1 C2 C3 38.9(3) . . . . ?
N1 C1 C2 C11 -80.4(2) . . . . ?
N1 C1 C2 N2 161.6(2) . . . . ?
N1 C18 C19 C20 176.8(3) . . . . ?
N1 C18 C23 C22 -175.4(5) . . . . ?
N2 C2 C3 C4 -150.1(2) . . . . ?
N2 C2 C3 C9 33.3(3) . . . . ?
N2 C2 C11 C10 -119.3(3) . . . . ?
N2 C2 C11 C12 62.5(3) . . . . ?
N2 C24 O4 C25 177.0(3) . . . . ?
N3 C10 C11 C2 -177.5(2) . . . . ?
N3 C10 C11 C12 1.1(3) . . . . ?
N3 C13 C14 C15 179.3(3) . . . . ?
O1 C1 C2 C3 -146.6(2) . . . . ?
O1 C1 C2 C11 94.1(3) . . . . ?
O1 C1 C2 N2 -23.8(3) . . . . ?
O1 C1 N1 C5 163.5(2) . . . . ?
O1 C1 N1 C18 -13.2(4) . . . . ?
O2 C5 N1 C1 174.0(2) . . . . ?
O2 C5 N1 C18 -9.4(4) . . . . ?
O3 C24 N2 C2 -6.9(4) . . . . ?
O3 C24 O4 C25 -2.0(5) . . . . ?
O4 C24 N2 C2 174.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20190237
_database_code_depnum_ccdc_archive 'CCDC 1917781'
loop_
_audit_author_name
_audit_author_address
'Yong You'
;Cheng Du University
China
;
_audit_update_record             
;
2019-05-22 deposited with the CCDC.	2019-06-25 downloaded from the CCDC.
;
_audit_creation_date             2019-02-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H17 N3 O2'
_chemical_formula_sum            'C23 H17 N3 O2'
_chemical_formula_weight         367.39
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C28H31ON5
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   8.05116(14)
_cell_length_b                   10.41903(19)
_cell_length_c                   21.8099(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1829.53(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5985
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.9810
_cell_measurement_theta_min      4.0420
_shelx_estimated_absorpt_T_max   0.940
_shelx_estimated_absorpt_T_min   0.902
_exptl_absorpt_coefficient_mu    0.701
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13473
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.919
_diffrn_reflns_theta_min         4.054
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -49.00   37.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000 -180.0000 86

#__ type_ start__ end____ width___ exp.time_
  2 omega -106.00    4.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -19.0000   60.0000 110

#__ type_ start__ end____ width___ exp.time_
  3 omega  -34.00   59.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000    0.0000 93

#__ type_ start__ end____ width___ exp.time_
  4 omega   -1.00  107.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000   60.0000 108

#__ type_ start__ end____ width___ exp.time_
  5 omega   17.00   49.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734 -122.0000  101.0000 32

#__ type_ start__ end____ width___ exp.time_
  6 omega   50.00  111.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734 -157.0000   35.0000 61

#__ type_ start__ end____ width___ exp.time_
  7 omega   11.00   38.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -19.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
  8 omega   12.00   46.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000  -60.0000 34

#__ type_ start__ end____ width___ exp.time_
  9 omega   11.00   65.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  150.0000 54

#__ type_ start__ end____ width___ exp.time_
 10 omega   45.00   72.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
 11 omega    1.00   59.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000 -120.0000 58

#__ type_ start__ end____ width___ exp.time_
 12 omega  -27.00    4.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -19.0000 -150.0000 31

#__ type_ start__ end____ width___ exp.time_
 13 omega   81.00  110.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  150.0000 29

#__ type_ start__ end____ width___ exp.time_
 14 omega   46.00   73.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
 15 omega   36.00  118.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -119.0000 -169.0000 82

#__ type_ start__ end____ width___ exp.time_
 16 omega   41.00   82.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 41

#__ type_ start__ end____ width___ exp.time_
 17 omega   40.00   89.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 49

#__ type_ start__ end____ width___ exp.time_
 18 omega   63.00   90.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
 19 omega   93.00  154.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000    0.0000 61

#__ type_ start__ end____ width___ exp.time_
 20 omega   37.00   68.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 31

#__ type_ start__ end____ width___ exp.time_
 21 omega   42.00   67.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 22 omega   47.00   97.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 50

#__ type_ start__ end____ width___ exp.time_
 23 omega   95.00  177.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -60.0000 82

#__ type_ start__ end____ width___ exp.time_
 24 omega   47.00   92.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 45

#__ type_ start__ end____ width___ exp.time_
 25 omega   87.00  132.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000    0.0000 45

#__ type_ start__ end____ width___ exp.time_
 26 omega   48.00  108.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 60

#__ type_ start__ end____ width___ exp.time_
 27 omega   44.00  107.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 63

#__ type_ start__ end____ width___ exp.time_
 28 omega   42.00   88.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 46

#__ type_ start__ end____ width___ exp.time_
 29 omega   79.00  107.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -60.0000 28

#__ type_ start__ end____ width___ exp.time_
 30 omega   55.00   83.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 28

#__ type_ start__ end____ width___ exp.time_
 31 omega   50.00   90.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 40

#__ type_ start__ end____ width___ exp.time_
 32 omega   42.00   90.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 48

#__ type_ start__ end____ width___ exp.time_
 33 omega   41.00  132.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000  -60.0000 91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1507779000
_diffrn_orient_matrix_UB_12      0.0237304000
_diffrn_orient_matrix_UB_13      0.0419610000
_diffrn_orient_matrix_UB_21      -0.1160997000
_diffrn_orient_matrix_UB_22      0.0070002000
_diffrn_orient_matrix_UB_23      0.0560268000
_diffrn_orient_matrix_UB_31      0.0189010000
_diffrn_orient_matrix_UB_32      -0.1458525000
_diffrn_orient_matrix_UB_33      0.0095145000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.722
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                3303
_reflns_number_total             3496
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 1327 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3496
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0378
_refine_ls_restrained_S_all      1.032
_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)+(0.0642P)²+0.1997P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1033
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C10(H10), C14(H14), C15(H15), C16(H16),
 C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.6078(4) 0.7756(3) 0.03212(11) 0.0429(6) Uani 1 1 d . . . . .
H1 H 0.6792 0.7382 0.0038 0.051 Uiso 1 1 calc R . . . .
C2 C 0.5229(4) 0.8874(3) 0.01878(12) 0.0477(6) Uani 1 1 d . . . . .
H2 H 0.5365 0.9256 -0.0194 0.057 Uiso 1 1 calc R . . . .
C3 C 0.4174(4) 0.9438(2) 0.06158(13) 0.0443(6) Uani 1 1 d . . . . .
H3 H 0.3626 1.0196 0.0517 0.053 Uiso 1 1 calc R . . . .
C4 C 0.3927(3) 0.8888(2) 0.11871(11) 0.0359(5) Uani 1 1 d . . . . .
H4 H 0.3229 0.9268 0.1474 0.043 Uiso 1 1 calc R . . . .
C5 C 0.4753(3) 0.7754(2) 0.13165(10) 0.0308(5) Uani 1 1 d . . . . .
C6 C 0.5824(3) 0.7211(2) 0.08944(10) 0.0339(5) Uani 1 1 d . . . . .
C7 C 0.6544(3) 0.6027(2) 0.11602(10) 0.0318(5) Uani 1 1 d . . . . .
C8 C 0.4657(3) 0.6898(2) 0.18825(10) 0.0290(4) Uani 1 1 d . . . . .
C9 C 0.5070(3) 0.7654(2) 0.24742(10) 0.0300(4) Uani 1 1 d . . . . .
C10 C 0.1832(3) 0.6128(2) 0.14941(11) 0.0381(5) Uani 1 1 d . . . . .
H10 H 0.1946 0.6451 0.1099 0.046 Uiso 1 1 calc R . . . .
C11 C 0.2952(3) 0.6300(2) 0.19532(10) 0.0313(4) Uani 1 1 d . . . . .
C12 C 0.2292(3) 0.5651(2) 0.24836(11) 0.0334(5) Uani 1 1 d . . . . .
C13 C 0.0766(3) 0.5096(2) 0.22971(13) 0.0387(5) Uani 1 1 d . . . . .
C14 C -0.0177(3) 0.4330(3) 0.26902(16) 0.0518(7) Uani 1 1 d . . . . .
H14 H -0.1156 0.3944 0.2558 0.062 Uiso 1 1 calc R . . . .
C15 C 0.0389(4) 0.4165(3) 0.32756(16) 0.0563(8) Uani 1 1 d . . . . .
H15 H -0.0218 0.3657 0.3545 0.068 Uiso 1 1 calc R . . . .
C16 C 0.1855(4) 0.4740(3) 0.34808(14) 0.0507(7) Uani 1 1 d . . . . .
H16 H 0.2190 0.4626 0.3885 0.061 Uiso 1 1 calc R . . . .
C17 C 0.2811(3) 0.5476(2) 0.30901(12) 0.0400(5) Uani 1 1 d . . . . .
H17 H 0.3790 0.5852 0.3229 0.048 Uiso 1 1 calc R . . . .
C18 C 0.6933(3) 0.7596(2) 0.33855(11) 0.0377(5) Uani 1 1 d . . . . .
C19 C 0.5849(4) 0.8113(3) 0.38144(12) 0.0461(6) Uani 1 1 d . . . . .
H19 H 0.4750 0.8284 0.3711 0.055 Uiso 1 1 calc R . . . .
C20 C 0.6430(6) 0.8372(3) 0.44001(14) 0.0616(9) Uani 1 1 d . . . . .
H20 H 0.5719 0.8739 0.4687 0.074 Uiso 1 1 calc R . . . .
C21 C 0.8038(6) 0.8095(4) 0.45628(15) 0.0708(11) Uani 1 1 d . . . . .
H21 H 0.8408 0.8266 0.4958 0.085 Uiso 1 1 calc R . . . .
C22 C 0.9105(5) 0.7563(4) 0.41370(16) 0.0661(9) Uani 1 1 d . . . . .
H22 H 1.0193 0.7372 0.4247 0.079 Uiso 1 1 calc R . . . .
C23 C 0.8558(4) 0.7313(3) 0.35465(14) 0.0502(6) Uani 1 1 d . . . . .
H23 H 0.9278 0.6958 0.3260 0.060 Uiso 1 1 calc R . . . .
N1 N 0.5928(2) 0.59290(18) 0.17412(9) 0.0312(4) Uani 1 1 d . . . . .
H1A H 0.591(4) 0.521(3) 0.1912(15) 0.045(8) Uiso 1 1 d . . . . .
N2 N 0.6419(3) 0.7258(2) 0.27822(9) 0.0355(4) Uani 1 1 d . . . . .
H2A H 0.704(4) 0.673(3) 0.2577(13) 0.037(7) Uiso 1 1 d . . . . .
N3 N 0.0518(3) 0.5417(2) 0.16953(11) 0.0438(5) Uani 1 1 d . . . . .
H3A H -0.030(5) 0.521(4) 0.1474(16) 0.058(10) Uiso 1 1 d . . . . .
O1 O 0.7513(2) 0.52651(18) 0.09255(8) 0.0422(4) Uani 1 1 d . . . . .
O2 O 0.4135(2) 0.85177(15) 0.26371(8) 0.0395(4) 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 H1 0.9300 . ?
C1 C2 1.381(4) . ?
C1 C6 1.388(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.392(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.386(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.385(3) . ?
C5 C6 1.382(3) . ?
C5 C8 1.525(3) . ?
C6 C7 1.481(3) . ?
C7 N1 1.364(3) . ?
C7 O1 1.225(3) . ?
C8 C9 1.548(3) . ?
C8 C11 1.515(3) . ?
C8 N1 1.470(3) . ?
C9 N2 1.343(3) . ?
C9 O2 1.226(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.359(3) . ?
C10 N3 1.364(4) . ?
C11 C12 1.441(3) . ?
C12 C13 1.417(3) . ?
C12 C17 1.399(4) . ?
C13 C14 1.396(4) . ?
C13 N3 1.369(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.366(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.397(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.381(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.388(4) . ?
C18 C23 1.386(4) . ?
C18 N2 1.424(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.387(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.373(6) . ?
C21 H21 0.9300 . ?
C21 C22 1.381(6) . ?
C22 H22 0.9300 . ?
C22 C23 1.386(4) . ?
C23 H23 0.9300 . ?
N1 H1A 0.84(4) . ?
N2 H2A 0.87(3) . ?
N3 H3A 0.85(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 121.2 . . ?
C2 C1 C6 117.5(2) . . ?
C6 C1 H1 121.2 . . ?
C1 C2 H2 119.4 . . ?
C1 C2 C3 121.1(2) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.0(2) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 121.1 . . ?
C5 C4 C3 117.8(2) . . ?
C5 C4 H4 121.1 . . ?
C4 C5 C8 129.7(2) . . ?
C6 C5 C4 120.9(2) . . ?
C6 C5 C8 109.35(19) . . ?
C1 C6 C7 129.5(2) . . ?
C5 C6 C1 121.6(2) . . ?
C5 C6 C7 108.9(2) . . ?
N1 C7 C6 106.47(19) . . ?
O1 C7 C6 128.7(2) . . ?
O1 C7 N1 124.8(2) . . ?
C5 C8 C9 111.48(17) . . ?
C11 C8 C5 111.66(18) . . ?
C11 C8 C9 108.60(18) . . ?
N1 C8 C5 101.33(17) . . ?
N1 C8 C9 112.00(18) . . ?
N1 C8 C11 111.69(17) . . ?
N2 C9 C8 115.75(19) . . ?
O2 C9 C8 118.9(2) . . ?
O2 C9 N2 125.3(2) . . ?
C11 C10 H10 124.8 . . ?
C11 C10 N3 110.4(2) . . ?
N3 C10 H10 124.8 . . ?
C10 C11 C8 125.4(2) . . ?
C10 C11 C12 106.6(2) . . ?
C12 C11 C8 127.5(2) . . ?
C13 C12 C11 106.3(2) . . ?
C17 C12 C11 135.2(2) . . ?
C17 C12 C13 118.5(2) . . ?
C14 C13 C12 121.9(3) . . ?
N3 C13 C12 107.6(2) . . ?
N3 C13 C14 130.5(3) . . ?
C13 C14 H14 121.2 . . ?
C15 C14 C13 117.7(3) . . ?
C15 C14 H14 121.2 . . ?
C14 C15 H15 119.1 . . ?
C14 C15 C16 121.8(3) . . ?
C16 C15 H15 119.1 . . ?
C15 C16 H16 119.6 . . ?
C17 C16 C15 120.8(3) . . ?
C17 C16 H16 119.6 . . ?
C12 C17 H17 120.4 . . ?
C16 C17 C12 119.2(2) . . ?
C16 C17 H17 120.4 . . ?
C19 C18 N2 122.4(2) . . ?
C23 C18 C19 120.3(3) . . ?
C23 C18 N2 117.1(3) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 C18 118.9(3) . . ?
C20 C19 H19 120.5 . . ?
C19 C20 H20 119.5 . . ?
C21 C20 C19 121.0(4) . . ?
C21 C20 H20 119.5 . . ?
C20 C21 H21 120.1 . . ?
C20 C21 C22 119.8(3) . . ?
C22 C21 H21 120.1 . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C23 120.2(3) . . ?
C23 C22 H22 119.9 . . ?
C18 C23 H23 120.2 . . ?
C22 C23 C18 119.7(3) . . ?
C22 C23 H23 120.2 . . ?
C7 N1 C8 113.34(18) . . ?
C7 N1 H1A 119(2) . . ?
C8 N1 H1A 121(2) . . ?
C9 N2 C18 128.4(2) . . ?
C9 N2 H2A 114(2) . . ?
C18 N2 H2A 118(2) . . ?
C10 N3 C13 109.1(2) . . ?
C10 N3 H3A 124(3) . . ?
C13 N3 H3A 127(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O2 0.84(4) 2.02(4) 2.855(2) 177(3) 4_645
N3 H3A O1 0.85(4) 2.13(4) 2.949(3) 163(4) 1_455

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 -0.7(4) . . . . ?
C1 C6 C7 N1 178.6(2) . . . . ?
C1 C6 C7 O1 -0.8(4) . . . . ?
C2 C1 C6 C5 0.6(4) . . . . ?
C2 C1 C6 C7 179.5(2) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
C3 C4 C5 C6 1.8(3) . . . . ?
C3 C4 C5 C8 -176.2(2) . . . . ?
C4 C5 C6 C1 -1.8(4) . . . . ?
C4 C5 C6 C7 179.0(2) . . . . ?
C4 C5 C8 C9 -56.5(3) . . . . ?
C4 C5 C8 C11 65.2(3) . . . . ?
C4 C5 C8 N1 -175.8(2) . . . . ?
C5 C6 C7 N1 -2.3(3) . . . . ?
C5 C6 C7 O1 178.3(2) . . . . ?
C5 C8 C9 N2 -117.3(2) . . . . ?
C5 C8 C9 O2 65.3(3) . . . . ?
C5 C8 C11 C10 22.5(3) . . . . ?
C5 C8 C11 C12 -166.9(2) . . . . ?
C5 C8 N1 C7 -7.8(2) . . . . ?
C6 C1 C2 C3 0.7(4) . . . . ?
C6 C5 C8 C9 125.4(2) . . . . ?
C6 C5 C8 C11 -113.0(2) . . . . ?
C6 C5 C8 N1 6.1(2) . . . . ?
C6 C7 N1 C8 6.6(3) . . . . ?
C8 C5 C6 C1 176.5(2) . . . . ?
C8 C5 C6 C7 -2.6(3) . . . . ?
C8 C9 N2 C18 -167.5(2) . . . . ?
C8 C11 C12 C13 -171.3(2) . . . . ?
C8 C11 C12 C17 8.7(4) . . . . ?
C9 C8 C11 C10 145.8(2) . . . . ?
C9 C8 C11 C12 -43.5(3) . . . . ?
C9 C8 N1 C7 -126.77(19) . . . . ?
C10 C11 C12 C13 0.8(3) . . . . ?
C10 C11 C12 C17 -179.2(3) . . . . ?
C11 C8 C9 N2 119.2(2) . . . . ?
C11 C8 C9 O2 -58.1(3) . . . . ?
C11 C8 N1 C7 111.2(2) . . . . ?
C11 C10 N3 C13 -0.6(3) . . . . ?
C11 C12 C13 C14 176.5(2) . . . . ?
C11 C12 C13 N3 -1.1(3) . . . . ?
C11 C12 C17 C16 -178.0(3) . . . . ?
C12 C13 C14 C15 2.4(4) . . . . ?
C12 C13 N3 C10 1.0(3) . . . . ?
C13 C12 C17 C16 2.0(4) . . . . ?
C13 C14 C15 C16 0.2(5) . . . . ?
C14 C13 N3 C10 -176.3(3) . . . . ?
C14 C15 C16 C17 -1.6(5) . . . . ?
C15 C16 C17 C12 0.4(4) . . . . ?
C17 C12 C13 C14 -3.5(4) . . . . ?
C17 C12 C13 N3 178.9(2) . . . . ?
C18 C19 C20 C21 -1.6(5) . . . . ?
C19 C18 C23 C22 -0.7(4) . . . . ?
C19 C18 N2 C9 19.2(4) . . . . ?
C19 C20 C21 C22 0.7(5) . . . . ?
C20 C21 C22 C23 0.3(5) . . . . ?
C21 C22 C23 C18 -0.2(5) . . . . ?
C23 C18 C19 C20 1.6(4) . . . . ?
C23 C18 N2 C9 -164.7(2) . . . . ?
N1 C8 C9 N2 -4.6(3) . . . . ?
N1 C8 C9 O2 178.0(2) . . . . ?
N1 C8 C11 C10 -90.2(3) . . . . ?
N1 C8 C11 C12 80.5(3) . . . . ?
N2 C18 C19 C20 177.6(2) . . . . ?
N2 C18 C23 C22 -176.9(3) . . . . ?
N3 C10 C11 C8 172.1(2) . . . . ?
N3 C10 C11 C12 -0.1(3) . . . . ?
N3 C13 C14 C15 179.4(3) . . . . ?
O1 C7 N1 C8 -173.9(2) . . . . ?
O2 C9 N2 C18 9.7(4) . . . . ?

_olex2_date_sample_data_collection 1551180331.22
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20190238
_database_code_depnum_ccdc_archive 'CCDC 1917782'
loop_
_audit_author_name
_audit_author_address
'Yong You'
;Cheng Du University
China
;
_audit_update_record             
;
2019-05-22 deposited with the CCDC.	2019-06-25 downloaded from the CCDC.
;
_audit_creation_date             2019-02-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H25 N3 O4'
_chemical_formula_sum            'C21 H25 N3 O4'
_chemical_formula_weight         383.44
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C28H31ON5
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_H-M_alt        'P 41 21 2'
_space_group_name_Hall           'P 4abw 2nw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y+1/2, x+1/2, z+1/4'
'-x, -y, z+1/2'
'y+1/2, -x+1/2, z+3/4'
'x+1/2, -y+1/2, -z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   10.81497(10)
_cell_length_b                   10.81497(10)
_cell_length_c                   37.0777(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4336.74(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7175
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.5840
_cell_measurement_theta_min      4.2390
_shelx_estimated_absorpt_T_max   0.930
_shelx_estimated_absorpt_T_min   0.900
_exptl_absorpt_coefficient_mu    0.671
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79333
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            18060
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.892
_diffrn_reflns_theta_min         4.258
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -13.00   36.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000  -60.0000 98

#__ type_ start__ end____ width___ exp.time_
  2 omega -100.00  -74.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000 -150.0000 52

#__ type_ start__ end____ width___ exp.time_
  3 omega  -55.00  -25.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -37.0000  -30.0000 60

#__ type_ start__ end____ width___ exp.time_
  4 omega  -32.00    3.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000  120.0000 70

#__ type_ start__ end____ width___ exp.time_
  5 omega   22.00   69.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   90.0000 94

#__ type_ start__ end____ width___ exp.time_
  6 omega   -3.00   23.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   60.0000 52

#__ type_ start__ end____ width___ exp.time_
  7 omega   16.00   44.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000  120.0000 56

#__ type_ start__ end____ width___ exp.time_
  8 omega   27.00   73.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   60.0000 92

#__ type_ start__ end____ width___ exp.time_
  9 omega   23.00  105.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  120.0000 164

#__ type_ start__ end____ width___ exp.time_
 10 omega   60.00   96.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -90.0000 72

#__ type_ start__ end____ width___ exp.time_
 11 omega   58.00   88.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  120.0000 60

#__ type_ start__ end____ width___ exp.time_
 12 omega   77.00  107.00   0.5000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 60

#__ type_ start__ end____ width___ exp.time_
 13 omega   49.00  105.00   0.5000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 112

#__ type_ start__ end____ width___ exp.time_
 14 omega   89.00  144.00   0.5000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   60.0000 110

#__ type_ start__ end____ width___ exp.time_
 15 omega   37.00   88.00   0.5000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 102

#__ type_ start__ end____ width___ exp.time_
 16 omega   54.00  109.00   0.5000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 110

#__ type_ start__ end____ width___ exp.time_
 17 omega   55.00  126.00   0.5000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  150.0000 142

#__ type_ start__ end____ width___ exp.time_
 18 omega   39.00   89.00   0.5000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 100

#__ type_ start__ end____ width___ exp.time_
 19 omega   38.00   70.00   0.5000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 64

#__ type_ start__ end____ width___ exp.time_
 20 omega   38.00   91.00   0.5000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 106

#__ type_ start__ end____ width___ exp.time_
 21 omega   59.00  127.00   0.5000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000 -120.0000 136
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0046067000
_diffrn_orient_matrix_UB_12      0.1353626000
_diffrn_orient_matrix_UB_13      -0.0128498000
_diffrn_orient_matrix_UB_21      0.1415092000
_diffrn_orient_matrix_UB_22      -0.0006373000
_diffrn_orient_matrix_UB_23      -0.0049174000
_diffrn_orient_matrix_UB_31      -0.0162123000
_diffrn_orient_matrix_UB_32      -0.0442663000
_diffrn_orient_matrix_UB_33      -0.0391952000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.659
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                3750
_reflns_number_total             4153
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.118
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 1359 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.20(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         4153
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0423
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0704P)²+0.2009P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1178
_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. Restrained distances
 N1-C14
 1.45 with sigma of 0.02
 N1-C14A
 1.45 with sigma of 0.02
 C14A-C15A
 1.55 with sigma of 0.02
 C15A-C16A
 1.55 with sigma of 0.02
 C15-C16
 1.55 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C14) = Uanis(C14A)
Uanis(C15) = Uanis(C15A)
Uanis(C16) = Uanis(C16A)
4. Others
 Sof(C14A)=Sof(H14C)=Sof(H14D)=Sof(C15A)=Sof(H15C)=Sof(H15D)=Sof(C16A)=
 Sof(H16D)=Sof(H16E)=Sof(H16F)=1-FVAR(1)
 Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(C16)=Sof(H16A)=
 Sof(H16B)=Sof(H16C)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C14A(H14C,H14D), C15(H15A,H15B), C15A(H15C,H15D)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C11(H11), C12(H12), C13(H13)
5.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C16A(H16D,H16E,H16F), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.9026(3) 0.2133(3) 0.60497(6) 0.0768(7) Uani 1 1 d . . . . .
H1 H 0.9630 0.2265 0.6224 0.092 Uiso 1 1 calc R . . . .
C2 C 0.8629(4) 0.0955(4) 0.59798(8) 0.0938(10) Uani 1 1 d . . . . .
H2 H 0.8969 0.0291 0.6104 0.113 Uiso 1 1 calc R . . . .
C3 C 0.7721(4) 0.0753(4) 0.57234(9) 0.0949(9) Uani 1 1 d . . . . .
H3 H 0.7443 -0.0046 0.5679 0.114 Uiso 1 1 calc R . . . .
C4 C 0.7224(3) 0.1737(3) 0.55331(7) 0.0800(7) Uani 1 1 d . . . . .
H4 H 0.6613 0.1598 0.5361 0.096 Uiso 1 1 calc R . . . .
C5 C 0.7636(2) 0.2926(3) 0.55985(5) 0.0610(6) Uani 1 1 d . . . . .
C6 C 0.8532(2) 0.3138(3) 0.58612(5) 0.0625(6) Uani 1 1 d . . . . .
C7 C 0.8961(2) 0.4391(3) 0.59519(5) 0.0626(6) Uani 1 1 d . . . . .
C8 C 0.71981(19) 0.3991(3) 0.53678(5) 0.0585(5) Uani 1 1 d . . . . .
C9 C 0.7439(2) 0.5268(3) 0.55391(6) 0.0632(6) Uani 1 1 d . . . . .
C10 C 0.7933(2) 0.3984(3) 0.50192(5) 0.0638(6) Uani 1 1 d . . . . .
C11 C 0.8860(3) 0.3228(4) 0.49067(7) 0.0887(10) Uani 1 1 d . . . . .
H11 H 0.9186 0.2555 0.5031 0.106 Uiso 1 1 calc R . . . .
C12 C 0.9232(3) 0.3665(5) 0.45643(8) 0.1081(14) Uani 1 1 d . . . . .
H12 H 0.9851 0.3327 0.4421 0.130 Uiso 1 1 calc R . . . .
C13 C 0.8537(3) 0.4650(4) 0.44836(7) 0.0976(11) Uani 1 1 d . . . . .
H13 H 0.8592 0.5118 0.4274 0.117 Uiso 1 1 calc R . . . .
C14 C 0.8687(4) 0.6701(5) 0.59146(12) 0.0685(10) Uani 0.741(5) 1 d D . P A 1
H14A H 0.7972 0.7228 0.5879 0.082 Uiso 0.741(5) 1 calc R . P A 1
H14B H 0.8865 0.6679 0.6171 0.082 Uiso 0.741(5) 1 calc R . P A 1
C14A C 0.8952(14) 0.6495(15) 0.5826(4) 0.0685(10) Uani 0.259(5) 1 d D . P A 2
H14C H 0.9508 0.6432 0.6031 0.082 Uiso 0.259(5) 1 calc R . P A 2
H14D H 0.8329 0.7106 0.5887 0.082 Uiso 0.259(5) 1 calc R . P A 2
C15 C 0.9790(4) 0.7254(5) 0.57160(14) 0.0858(12) Uani 0.741(5) 1 d D . P A 1
H15A H 0.9987 0.8047 0.5824 0.103 Uiso 0.741(5) 1 calc R . P A 1
H15B H 1.0498 0.6717 0.5751 0.103 Uiso 0.741(5) 1 calc R . P A 1
C15A C 0.9677(13) 0.6972(13) 0.5510(4) 0.0858(12) Uani 0.259(5) 1 d D . P A 2
H15C H 1.0365 0.6425 0.5459 0.103 Uiso 0.259(5) 1 calc R . P A 2
H15D H 0.9153 0.7008 0.5298 0.103 Uiso 0.259(5) 1 calc R . P A 2
C16 C 0.9600(7) 0.7439(7) 0.53195(15) 0.126(2) Uani 0.741(5) 1 d D . P A 1
H16A H 0.9579 0.6650 0.5201 0.189 Uiso 0.741(5) 1 calc GR . P A 1
H16B H 1.0267 0.7923 0.5224 0.189 Uiso 0.741(5) 1 calc GR . P A 1
H16C H 0.8832 0.7862 0.5280 0.189 Uiso 0.741(5) 1 calc GR . P A 1
C16A C 1.0145(19) 0.8242(17) 0.5601(4) 0.126(2) Uani 0.259(5) 1 d D . P A 2
H16D H 1.0843 0.8434 0.5451 0.189 Uiso 0.259(5) 1 calc GR . P A 2
H16E H 1.0391 0.8265 0.5850 0.189 Uiso 0.259(5) 1 calc GR . P A 2
H16F H 0.9502 0.8837 0.5560 0.189 Uiso 0.259(5) 1 calc GR . P A 2
C17 C 0.5064(2) 0.4054(3) 0.55590(5) 0.0598(5) Uani 1 1 d . . . . .
C18 C 0.2835(2) 0.4140(3) 0.56610(6) 0.0729(7) Uani 1 1 d . . . . .
C19 C 0.2847(3) 0.5270(4) 0.58972(11) 0.1089(13) Uani 1 1 d . . . . .
H19A H 0.3520 0.5214 0.6065 0.163 Uiso 1 1 calc GR . . . .
H19B H 0.2080 0.5323 0.6027 0.163 Uiso 1 1 calc GR . . . .
H19C H 0.2948 0.5994 0.5750 0.163 Uiso 1 1 calc GR . . . .
C20 C 0.2799(4) 0.2980(4) 0.58835(13) 0.1188(14) Uani 1 1 d . . . . .
H20A H 0.2836 0.2273 0.5727 0.178 Uiso 1 1 calc GR . . . .
H20B H 0.2045 0.2957 0.6020 0.178 Uiso 1 1 calc GR . . . .
H20C H 0.3492 0.2969 0.6045 0.178 Uiso 1 1 calc GR . . . .
C21 C 0.1785(3) 0.4183(5) 0.53909(9) 0.1126(15) Uani 1 1 d . . . . .
H21A H 0.1827 0.4940 0.5256 0.169 Uiso 1 1 calc GR . . . .
H21B H 0.1010 0.4141 0.5516 0.169 Uiso 1 1 calc GR . . . .
H21C H 0.1853 0.3494 0.5229 0.169 Uiso 1 1 calc GR . . . .
N1 N 0.83834(18) 0.5396(2) 0.57851(5) 0.0645(5) Uani 1 1 d D . . . .
N2 N 0.58876(17) 0.3901(2) 0.52867(5) 0.0643(5) Uani 1 1 d . . . . .
H2A H 0.564(2) 0.393(3) 0.5070(8) 0.062(7) Uiso 1 1 d . . . . .
N3 N 0.7744(2) 0.4851(3) 0.47586(5) 0.0763(6) Uani 1 1 d . . . . .
H3A H 0.722(3) 0.554(3) 0.4779(7) 0.066(7) Uiso 1 1 d . . . . .
O1 O 0.97712(18) 0.4585(2) 0.61721(5) 0.0851(6) Uani 1 1 d . . . . .
O2 O 0.68662(19) 0.6162(2) 0.54368(5) 0.0846(6) Uani 1 1 d . . . . .
O3 O 0.53585(15) 0.4096(2) 0.58725(4) 0.0735(5) Uani 1 1 d . . . . .
O4 O 0.39262(14) 0.4145(2) 0.54249(4) 0.0724(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9300 . ?
C1 C2 1.369(5) . ?
C1 C6 1.399(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.384(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(4) . ?
C5 C6 1.393(3) . ?
C5 C8 1.511(3) . ?
C6 C7 1.471(4) . ?
C7 N1 1.398(3) . ?
C7 O1 1.216(3) . ?
C8 C9 1.543(4) . ?
C8 C10 1.517(3) . ?
C8 N2 1.452(3) . ?
C9 N1 1.376(3) . ?
C9 O2 1.209(3) . ?
C10 C11 1.360(4) . ?
C10 N3 1.362(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.413(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.338(6) . ?
C13 H13 0.9300 . ?
C13 N3 1.350(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.524(6) . ?
C14 N1 1.527(5) . ?
C14A H14C 0.9700 . ?
C14A H14D 0.9700 . ?
C14A C15A 1.502(18) . ?
C14A N1 1.346(16) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.498(8) . ?
C15A H15C 0.9700 . ?
C15A H15D 0.9700 . ?
C15A C16A 1.502(19) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C16A H16D 0.9600 . ?
C16A H16E 0.9600 . ?
C16A H16F 0.9600 . ?
C17 N2 1.356(3) . ?
C17 O3 1.206(3) . ?
C17 O4 1.331(3) . ?
C18 C19 1.503(5) . ?
C18 C20 1.502(5) . ?
C18 C21 1.515(4) . ?
C18 O4 1.469(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
N2 H2A 0.85(3) . ?
N3 H3A 0.93(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 119.7 . . ?
C2 C1 C6 120.6(3) . . ?
C6 C1 H1 119.7 . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 120.0(3) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.3(4) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.0(2) . . ?
C4 C5 C8 120.6(2) . . ?
C6 C5 C8 119.3(2) . . ?
C1 C6 C7 118.8(2) . . ?
C5 C6 C1 119.2(3) . . ?
C5 C6 C7 122.0(2) . . ?
N1 C7 C6 118.30(19) . . ?
O1 C7 C6 122.6(2) . . ?
O1 C7 N1 119.0(3) . . ?
C5 C8 C9 113.36(18) . . ?
C5 C8 C10 108.30(19) . . ?
C10 C8 C9 105.5(2) . . ?
N2 C8 C5 111.8(2) . . ?
N2 C8 C9 108.10(19) . . ?
N2 C8 C10 109.54(16) . . ?
N1 C9 C8 119.2(2) . . ?
O2 C9 C8 120.0(2) . . ?
O2 C9 N1 120.5(3) . . ?
C11 C10 C8 130.6(2) . . ?
C11 C10 N3 107.9(2) . . ?
N3 C10 C8 121.4(2) . . ?
C10 C11 H11 126.7 . . ?
C10 C11 C12 106.5(3) . . ?
C12 C11 H11 126.7 . . ?
C11 C12 H12 126.0 . . ?
C13 C12 C11 107.9(3) . . ?
C13 C12 H12 126.0 . . ?
C12 C13 H13 125.8 . . ?
C12 C13 N3 108.5(3) . . ?
N3 C13 H13 125.8 . . ?
H14A C14 H14B 107.9 . . ?
C15 C14 H14A 109.1 . . ?
C15 C14 H14B 109.1 . . ?
C15 C14 N1 112.3(3) . . ?
N1 C14 H14A 109.1 . . ?
N1 C14 H14B 109.1 . . ?
H14C C14A H14D 107.3 . . ?
C15A C14A H14C 108.1 . . ?
C15A C14A H14D 108.1 . . ?
N1 C14A H14C 108.1 . . ?
N1 C14A H14D 108.1 . . ?
N1 C14A C15A 116.9(10) . . ?
C14 C15 H15A 108.6 . . ?
C14 C15 H15B 108.6 . . ?
H15A C15 H15B 107.6 . . ?
C16 C15 C14 114.8(5) . . ?
C16 C15 H15A 108.6 . . ?
C16 C15 H15B 108.6 . . ?
C14A C15A H15C 110.0 . . ?
C14A C15A H15D 110.0 . . ?
H15C C15A H15D 108.4 . . ?
C16A C15A C14A 108.3(13) . . ?
C16A C15A H15C 110.0 . . ?
C16A C15A H15D 110.0 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15A C16A H16D 109.5 . . ?
C15A C16A H16E 109.5 . . ?
C15A C16A H16F 109.5 . . ?
H16D C16A H16E 109.5 . . ?
H16D C16A H16F 109.5 . . ?
H16E C16A H16F 109.5 . . ?
O3 C17 N2 123.3(2) . . ?
O3 C17 O4 126.9(2) . . ?
O4 C17 N2 109.74(17) . . ?
C19 C18 C21 111.5(3) . . ?
C20 C18 C19 111.0(3) . . ?
C20 C18 C21 111.6(3) . . ?
O4 C18 C19 109.7(3) . . ?
O4 C18 C20 110.6(3) . . ?
O4 C18 C21 102.00(19) . . ?
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 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 . . ?
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 . . ?
C7 N1 C14 118.9(2) . . ?
C9 N1 C7 123.2(2) . . ?
C9 N1 C14 117.5(3) . . ?
C14A N1 C7 115.6(7) . . ?
C14A N1 C9 120.2(8) . . ?
C8 N2 H2A 120.2(18) . . ?
C17 N2 C8 118.56(17) . . ?
C17 N2 H2A 119.5(19) . . ?
C10 N3 H3A 125.4(17) . . ?
C13 N3 C10 109.2(3) . . ?
C13 N3 H3A 125.0(17) . . ?
C17 O4 C18 121.32(16) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O4 0.85(3) 2.44(3) 3.242(3) 157(2) 7_556
N3 H3A O2 0.93(3) 2.01(3) 2.864(3) 152(2) 7_556

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 1.0(5) . . . . ?
C1 C6 C7 N1 -174.4(2) . . . . ?
C1 C6 C7 O1 3.6(3) . . . . ?
C2 C1 C6 C5 -0.5(4) . . . . ?
C2 C1 C6 C7 178.4(2) . . . . ?
C2 C3 C4 C5 0.1(5) . . . . ?
C3 C4 C5 C6 -1.4(4) . . . . ?
C3 C4 C5 C8 173.8(3) . . . . ?
C4 C5 C6 C1 1.6(3) . . . . ?
C4 C5 C6 C7 -177.3(2) . . . . ?
C4 C5 C8 C9 163.5(2) . . . . ?
C4 C5 C8 C10 -79.8(3) . . . . ?
C4 C5 C8 N2 41.0(3) . . . . ?
C5 C6 C7 N1 4.5(3) . . . . ?
C5 C6 C7 O1 -177.5(2) . . . . ?
C5 C8 C9 N1 25.2(3) . . . . ?
C5 C8 C9 O2 -160.5(2) . . . . ?
C5 C8 C10 C11 -1.6(4) . . . . ?
C5 C8 C10 N3 -179.4(2) . . . . ?
C5 C8 N2 C17 68.4(3) . . . . ?
C6 C1 C2 C3 -0.7(5) . . . . ?
C6 C5 C8 C9 -21.2(3) . . . . ?
C6 C5 C8 C10 95.4(2) . . . . ?
C6 C5 C8 N2 -143.8(2) . . . . ?
C6 C7 N1 C9 -0.4(3) . . . . ?
C6 C7 N1 C14 171.4(2) . . . . ?
C6 C7 N1 C14A -168.4(6) . . . . ?
C8 C5 C6 C1 -173.7(2) . . . . ?
C8 C5 C6 C7 7.5(3) . . . . ?
C8 C9 N1 C7 -15.1(3) . . . . ?
C8 C9 N1 C14 173.0(2) . . . . ?
C8 C9 N1 C14A 152.4(6) . . . . ?
C8 C10 C11 C12 -178.2(3) . . . . ?
C8 C10 N3 C13 178.4(3) . . . . ?
C9 C8 C10 C11 120.1(3) . . . . ?
C9 C8 C10 N3 -57.8(3) . . . . ?
C9 C8 N2 C17 -57.1(3) . . . . ?
C10 C8 C9 N1 -93.1(2) . . . . ?
C10 C8 C9 O2 81.2(3) . . . . ?
C10 C8 N2 C17 -171.5(2) . . . . ?
C10 C11 C12 C13 0.2(5) . . . . ?
C11 C10 N3 C13 0.1(4) . . . . ?
C11 C12 C13 N3 -0.2(5) . . . . ?
C12 C13 N3 C10 0.1(4) . . . . ?
C15 C14 N1 C7 89.0(4) . . . . ?
C15 C14 N1 C9 -98.8(4) . . . . ?
C15A C14A N1 C7 103.2(13) . . . . ?
C15A C14A N1 C9 -65.2(14) . . . . ?
C19 C18 O4 C17 64.9(4) . . . . ?
C20 C18 O4 C17 -57.9(4) . . . . ?
C21 C18 O4 C17 -176.7(3) . . . . ?
N1 C14 C15 C16 63.6(6) . . . . ?
N1 C14A C15A C16A 175.5(14) . . . . ?
N2 C8 C9 N1 149.75(19) . . . . ?
N2 C8 C9 O2 -35.9(3) . . . . ?
N2 C8 C10 C11 -123.8(3) . . . . ?
N2 C8 C10 N3 58.4(3) . . . . ?
N2 C17 O4 C18 171.2(3) . . . . ?
N3 C10 C11 C12 -0.2(4) . . . . ?
O1 C7 N1 C9 -178.4(2) . . . . ?
O1 C7 N1 C14 -6.6(3) . . . . ?
O1 C7 N1 C14A 13.5(6) . . . . ?
O2 C9 N1 C7 170.6(2) . . . . ?
O2 C9 N1 C14 -1.3(4) . . . . ?
O2 C9 N1 C14A -21.9(7) . . . . ?
O3 C17 N2 C8 -10.4(4) . . . . ?
O3 C17 O4 C18 -8.7(5) . . . . ?
O4 C17 N2 C8 169.7(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
