# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

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

data_exp_1669
_database_code_depnum_ccdc_archive 'CCDC 1874506'
loop_
_audit_author_name
_audit_author_address
'Zhixiong Ruan '
; Guangzhou Medical University, 195# Dongfengxi Road, Guangzhou 510182
China
;
_audit_update_record             
;
2018-10-22 deposited with the CCDC.	2020-10-19 downloaded from the CCDC.
;
_audit_creation_date             2018-10-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C33 H36 N6 O2'
_chemical_formula_sum            'C33 H36 N6 O2'
_chemical_formula_weight         548.68
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.3769(9)
_cell_length_b                   12.1582(12)
_cell_length_c                   13.2260(8)
_cell_angle_alpha                78.192(6)
_cell_angle_beta                 79.374(6)
_cell_angle_gamma                63.184(9)
_cell_volume                     1589.3(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5171
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.6980
_cell_measurement_theta_min      3.2950
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.583
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66667
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.147
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10734
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.900
_diffrn_reflns_theta_min         3.433
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      9.00  37.00   1.00    1.00    --   40.48  77.00  60.00   28
  2  ω     86.00 177.00   1.00    1.00    --  107.58  45.00 -30.00   91
  3  ω    148.00 178.00   1.00    1.00    --  107.58 125.00-120.00   30
  4  ω    101.00 128.00   1.00    1.00    --  107.58 -30.00  30.00   27
  5  ω     67.00 121.00   1.00    1.00    --  107.58-125.00  60.00   54
  6  ω     35.00 133.00   1.00    1.00    --  107.58 -30.00 -60.00   98
  7  ω     93.00 120.00   1.00    1.00    --  107.58 -45.00-180.00   27
  8  ω     48.00 120.00   1.00    1.00    --  107.58-125.00-120.00   72
  9  ω     38.00 135.00   1.00    1.00    --  107.58 -77.00-120.00   97
 10  ω     39.00  66.00   1.00    1.00    --  107.58 -45.00-180.00   27
 11  ω      3.00  81.00   1.00    1.00    --   40.48 -99.00 -90.00   78
 12  ω     39.00  66.00   1.00    1.00    --  107.58 -30.00  30.00   27
 13  ω     39.00 112.00   1.00    1.00    --  107.58 -45.00  60.00   73
 14  ω     37.00  88.00   1.00    1.00    --  107.58 -95.00  60.00   51
 15  ω     31.00 157.00   1.00    1.00    --  107.58 -15.00 150.00  126
 16  ω    -64.00  30.00   1.00    1.00    --  -40.48  57.00-150.00   94
 17  ω   -110.00 -18.00   1.00    1.00    --  -40.48 -57.00  60.00   92
 18  ω   -112.00 -19.00   1.00    1.00    --  -40.48 -38.00 -60.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1247689000
_diffrn_orient_matrix_UB_12      -0.0379757000
_diffrn_orient_matrix_UB_13      0.0534644000
_diffrn_orient_matrix_UB_21      -0.0675717000
_diffrn_orient_matrix_UB_22      0.1223676000
_diffrn_orient_matrix_UB_23      0.0475824000
_diffrn_orient_matrix_UB_31      -0.0560981000
_diffrn_orient_matrix_UB_32      -0.0643112000
_diffrn_orient_matrix_UB_33      0.0959015000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5200
_reflns_number_total             6204
_reflns_odcompleteness_completeness 99.86
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.560
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         6204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0680
_refine_ls_restrained_S_all      1.013
_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)+(0.1269P)²+0.6500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1927
_refine_ls_wR_factor_ref         0.2031
_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:
 C18(H18), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C32(H32A,H32B), C19(H19A,H19B), C23(H23A,H23B), C22(H22A,H22B), C20(H20A,
 H20B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 N6(H6), C13(H13), C27(H27), C8(H8), C5(H5), C2(H2), C28(H28), C4(H4),
 C31(H31), C29(H29), C3(H3), C30(H30), C10(H10)
2.d Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C16(H16A,H16B,H16C), C15(H15A,H15B,H15C)
;
_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 0.78825(14) 0.17411(14) 0.47728(11) 0.0355(3) Uani 1 1 d . . . . .
O1 O 0.62631(15) 0.28337(14) 0.37478(11) 0.0374(4) Uani 1 1 d . . . . .
N1 N 0.33039(15) 0.20026(15) 0.71335(12) 0.0271(3) Uani 1 1 d . . . . .
N2 N 0.44241(15) 0.13198(14) 0.92724(12) 0.0277(4) Uani 1 1 d . . . . .
N3 N 0.50904(17) 0.26037(15) 0.97568(13) 0.0312(4) Uani 1 1 d . . . . .
N5 N 0.36285(17) 0.37960(15) 0.69892(13) 0.0334(4) Uani 1 1 d . . . . .
N6 N 0.39065(17) 0.29231(17) 0.44064(13) 0.0375(4) Uani 1 1 d . . . . .
H6 H 0.441618 0.277540 0.383503 0.045 Uiso 1 1 calc R . . . .
N4 N 0.4550(2) 0.42371(17) 0.82770(14) 0.0385(4) Uani 1 1 d . . . . .
C6 C 0.25039(18) 0.14206(18) 0.76381(15) 0.0287(4) Uani 1 1 d . . . . .
C7 C 0.35203(18) 0.18716(18) 0.60791(15) 0.0283(4) Uani 1 1 d . . . . .
C25 C 0.6613(2) 0.21852(18) 0.45763(15) 0.0313(4) Uani 1 1 d . . . . .
C24 C 0.57671(19) 0.18098(18) 0.54076(15) 0.0295(4) Uani 1 1 d . . . . .
C12 C 0.41760(18) 0.23678(17) 0.85336(14) 0.0268(4) Uani 1 1 d . . . . .
C1 C 0.22262(19) 0.09208(18) 0.68888(15) 0.0304(4) Uani 1 1 d . . . . .
C13 C 0.49684(19) 0.15088(18) 0.99684(15) 0.0295(4) Uani 1 1 d . . . . .
H13 H 0.525074 0.094250 1.056151 0.035 Uiso 1 1 calc R . . . .
C17 C 0.4442(2) 0.22442(18) 0.52894(14) 0.0297(4) Uani 1 1 d . . . . .
C9 C 0.36952(18) 0.27303(17) 0.75676(14) 0.0273(4) Uani 1 1 d . . . . .
C11 C 0.4588(2) 0.31726(18) 0.88236(15) 0.0307(4) Uani 1 1 d . . . . .
C27 C 0.62787(19) -0.01023(19) 0.67639(15) 0.0317(4) Uani 1 1 d . . . . .
H27 H 0.586731 -0.039623 0.641062 0.038 Uiso 1 1 calc R . . . .
C8 C 0.28819(19) 0.12209(18) 0.59222(15) 0.0311(4) Uani 1 1 d . . . . .
H8 H 0.287370 0.100633 0.528860 0.037 Uiso 1 1 calc R . . . .
C26 C 0.63447(18) 0.10280(18) 0.63724(15) 0.0297(4) Uani 1 1 d . . . . .
C5 C 0.1932(2) 0.1360(2) 0.86651(16) 0.0342(4) Uani 1 1 d . . . . .
H5 H 0.209503 0.171553 0.915174 0.041 Uiso 1 1 calc R . . . .
C2 C 0.1394(2) 0.0316(2) 0.71864(17) 0.0363(5) Uani 1 1 d . . . . .
H2 H 0.120743 -0.002332 0.670147 0.044 Uiso 1 1 calc R . . . .
C28 C 0.6822(2) -0.0794(2) 0.76766(16) 0.0375(5) Uani 1 1 d . . . . .
H28 H 0.676825 -0.154435 0.792802 0.045 Uiso 1 1 calc R . . . .
C32 C 0.8715(2) 0.2177(2) 0.39864(17) 0.0385(5) Uani 1 1 d . . . . .
H32A H 0.844425 0.305582 0.398920 0.046 Uiso 1 1 calc R . . . .
H32B H 0.863312 0.206056 0.330306 0.046 Uiso 1 1 calc R . . . .
C4 C 0.1117(2) 0.0756(2) 0.89365(17) 0.0391(5) Uani 1 1 d . . . . .
H4 H 0.073435 0.069731 0.961842 0.047 Uiso 1 1 calc R . . . .
C31 C 0.6963(2) 0.1437(2) 0.69335(16) 0.0344(4) Uani 1 1 d . . . . .
H31 H 0.700881 0.219301 0.669513 0.041 Uiso 1 1 calc R . . . .
C29 C 0.7437(2) -0.0377(2) 0.82103(17) 0.0426(5) Uani 1 1 d . . . . .
H29 H 0.780167 -0.084340 0.881828 0.051 Uiso 1 1 calc R . . . .
C18 C 0.2555(2) 0.38788(19) 0.43231(16) 0.0351(5) Uani 1 1 d . . . . .
H18 H 0.201646 0.383250 0.498604 0.042 Uiso 1 1 calc R . . . .
C14 C 0.5658(2) 0.3110(2) 1.03647(17) 0.0388(5) Uani 1 1 d . . . . .
H14 H 0.507887 0.400000 1.036056 0.047 Uiso 1 1 calc R . . . .
C3 C 0.0856(2) 0.0230(2) 0.82054(19) 0.0408(5) Uani 1 1 d . . . . .
H3 H 0.031398 -0.018097 0.840984 0.049 Uiso 1 1 calc R . . . .
C30 C 0.7507(2) 0.0741(2) 0.78354(17) 0.0413(5) Uani 1 1 d . . . . .
H30 H 0.792363 0.102717 0.819179 0.050 Uiso 1 1 calc R . . . .
C10 C 0.4056(2) 0.4477(2) 0.73757(17) 0.0391(5) Uani 1 1 d . . . . .
H10 H 0.399892 0.521140 0.695948 0.047 Uiso 1 1 calc R . . . .
C33 C 1.0113(2) 0.1444(2) 0.4234(2) 0.0460(6) Uani 1 1 d . . . . .
H33A H 1.067605 0.174244 0.374453 0.069 Uiso 1 1 calc GR . . . .
H33B H 1.038677 0.058136 0.419332 0.069 Uiso 1 1 calc GR . . . .
H33C H 1.017639 0.153571 0.492303 0.069 Uiso 1 1 calc GR . . . .
C16 C 0.5699(3) 0.2494(2) 1.14794(18) 0.0461(6) Uani 1 1 d . . . . .
H16A H 0.482946 0.257511 1.176699 0.069 Uiso 1 1 calc GR . . . .
H16B H 0.599235 0.288707 1.187365 0.069 Uiso 1 1 calc GR . . . .
H16C H 0.630108 0.162831 1.150651 0.069 Uiso 1 1 calc GR . . . .
C19 C 0.1968(2) 0.3685(2) 0.34748(18) 0.0420(5) Uani 1 1 d . . . . .
H19A H 0.190384 0.289865 0.366474 0.050 Uiso 1 1 calc R . . . .
H19B H 0.255587 0.363814 0.283638 0.050 Uiso 1 1 calc R . . . .
C23 C 0.2577(2) 0.5170(2) 0.4074(2) 0.0489(6) Uani 1 1 d . . . . .
H23A H 0.286482 0.532058 0.465725 0.059 Uiso 1 1 calc R . . . .
H23B H 0.321245 0.517278 0.347401 0.059 Uiso 1 1 calc R . . . .
C22 C 0.1229(3) 0.6206(2) 0.3854(2) 0.0559(7) Uani 1 1 d . . . . .
H22A H 0.062022 0.627572 0.448175 0.067 Uiso 1 1 calc R . . . .
H22B H 0.130046 0.698879 0.364952 0.067 Uiso 1 1 calc R . . . .
C15 C 0.7009(3) 0.2976(3) 0.9854(2) 0.0621(8) Uani 1 1 d . . . . .
H15A H 0.761221 0.210961 0.989521 0.093 Uiso 1 1 calc GR . . . .
H15B H 0.732478 0.339293 1.020296 0.093 Uiso 1 1 calc GR . . . .
H15C H 0.694733 0.333979 0.913806 0.093 Uiso 1 1 calc GR . . . .
C20 C 0.0618(3) 0.4711(3) 0.3286(2) 0.0558(7) Uani 1 1 d . . . . .
H20A H 0.000642 0.472609 0.390616 0.067 Uiso 1 1 calc R . . . .
H20B H 0.029162 0.455767 0.272588 0.067 Uiso 1 1 calc R . . . .
C21 C 0.0688(3) 0.5967(3) 0.3001(2) 0.0628(8) Uani 1 1 d . . . . .
H21A H 0.125434 0.596994 0.235603 0.075 Uiso 1 1 calc R . . . .
H21B H -0.019002 0.662563 0.289790 0.075 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C25 1.350(3) . ?
O2 C32 1.457(2) . ?
O1 C25 1.227(2) . ?
N1 C6 1.392(3) . ?
N1 C7 1.400(2) . ?
N1 C9 1.403(2) . ?
N2 C12 1.388(2) . ?
N2 C13 1.307(2) . ?
N3 C13 1.367(3) . ?
N3 C11 1.372(3) . ?
N3 C14 1.482(3) . ?
N5 C9 1.340(2) . ?
N5 C10 1.346(3) . ?
N6 C17 1.353(3) . ?
N6 C18 1.457(3) . ?
N4 C11 1.333(3) . ?
N4 C10 1.334(3) . ?
C6 C1 1.409(3) . ?
C6 C5 1.396(3) . ?
C7 C17 1.493(3) . ?
C7 C8 1.356(3) . ?
C25 C24 1.464(3) . ?
C24 C17 1.382(3) . ?
C24 C26 1.488(3) . ?
C12 C9 1.391(3) . ?
C12 C11 1.399(3) . ?
C1 C8 1.424(3) . ?
C1 C2 1.401(3) . ?
C27 C26 1.396(3) . ?
C27 C28 1.392(3) . ?
C26 C31 1.397(3) . ?
C5 C4 1.383(3) . ?
C2 C3 1.378(3) . ?
C28 C29 1.377(3) . ?
C32 C33 1.492(3) . ?
C4 C3 1.401(3) . ?
C31 C30 1.382(3) . ?
C29 C30 1.381(4) . ?
C18 C19 1.512(3) . ?
C18 C23 1.548(3) . ?
C14 C16 1.510(3) . ?
C14 C15 1.510(4) . ?
C19 C20 1.504(3) . ?
C23 C22 1.515(3) . ?
C22 C21 1.513(4) . ?
C20 C21 1.532(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
C25 O2 C32 115.20(16) . . ?
C6 N1 C7 108.27(16) . . ?
C6 N1 C9 126.34(16) . . ?
C7 N1 C9 124.96(16) . . ?
C13 N2 C12 103.39(16) . . ?
C13 N3 C11 105.74(16) . . ?
C13 N3 C14 129.24(17) . . ?
C11 N3 C14 125.00(17) . . ?
C9 N5 C10 117.41(17) . . ?
C17 N6 C18 126.76(17) . . ?
C10 N4 C11 111.59(18) . . ?
N1 C6 C1 107.64(17) . . ?
N1 C6 C5 130.92(18) . . ?
C5 C6 C1 121.28(18) . . ?
N1 C7 C17 125.23(17) . . ?
C8 C7 N1 108.78(17) . . ?
C8 C7 C17 125.56(18) . . ?
O2 C25 C24 114.50(17) . . ?
O1 C25 O2 119.78(18) . . ?
O1 C25 C24 125.72(19) . . ?
C25 C24 C26 118.99(17) . . ?
C17 C24 C25 118.77(18) . . ?
C17 C24 C26 122.16(17) . . ?
N2 C12 C9 133.86(18) . . ?
N2 C12 C11 110.64(16) . . ?
C9 C12 C11 115.36(17) . . ?
C6 C1 C8 106.68(17) . . ?
C2 C1 C6 119.42(19) . . ?
C2 C1 C8 133.85(19) . . ?
N2 C13 N3 114.80(17) . . ?
N6 C17 C7 114.17(17) . . ?
N6 C17 C24 123.08(18) . . ?
C24 C17 C7 122.36(17) . . ?
N5 C9 N1 116.74(17) . . ?
N5 C9 C12 120.36(18) . . ?
C12 C9 N1 122.87(17) . . ?
N3 C11 C12 105.42(17) . . ?
N4 C11 N3 127.82(18) . . ?
N4 C11 C12 126.70(18) . . ?
C28 C27 C26 120.8(2) . . ?
C7 C8 C1 108.64(17) . . ?
C27 C26 C24 122.89(18) . . ?
C31 C26 C24 119.48(18) . . ?
C31 C26 C27 117.62(18) . . ?
C4 C5 C6 118.0(2) . . ?
C3 C2 C1 119.3(2) . . ?
C29 C28 C27 120.5(2) . . ?
O2 C32 C33 107.97(18) . . ?
C5 C4 C3 121.3(2) . . ?
C30 C31 C26 121.3(2) . . ?
C28 C29 C30 119.5(2) . . ?
N6 C18 C19 110.20(17) . . ?
N6 C18 C23 108.75(18) . . ?
C19 C18 C23 110.02(19) . . ?
N3 C14 C16 110.79(18) . . ?
N3 C14 C15 109.93(19) . . ?
C15 C14 C16 112.1(2) . . ?
C2 C3 C4 120.7(2) . . ?
C29 C30 C31 120.3(2) . . ?
N4 C10 N5 128.6(2) . . ?
C18 C19 C20 112.63(19) . . ?
C22 C23 C18 112.0(2) . . ?
C21 C22 C23 111.4(2) . . ?
C19 C20 C21 110.1(2) . . ?
C22 C21 C20 110.4(2) . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.500 0.000 225.4 52.0 ?
2 0.500 0.500 0.500 12.6 0.2 ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.426
_oxdiff_exptl_absorpt_empirical_full_min 0.554
####################################################################### 
# 
# 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_d-2-19
_database_code_depnum_ccdc_archive 'CCDC 1992408'
loop_
_audit_author_name
_audit_author_address
'Xu Zhongnan'
;Guangzhou Medical University, Xinzao Town, Panyu District, Guangzhou City, Guangdong Province
China
;
_audit_update_record             
;
2020-03-30 deposited with the CCDC.	2020-10-19 downloaded from the CCDC.
;
_audit_creation_date             2019-12-23
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H29 F N6 O'
_chemical_formula_sum            'C31 H29 F N6 O'
_chemical_formula_weight         520.60
_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'
F F 0.0171 0.0103 '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/n 1'
_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                   13.5375(12)
_cell_length_b                   12.2153(10)
_cell_length_c                   16.3297(14)
_cell_angle_alpha                90
_cell_angle_beta                 102.160(9)
_cell_angle_gamma                90
_cell_volume                     2639.8(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2667
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.4530
_cell_measurement_theta_min      2.2630
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11453
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.099
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -6.00  27.00   1.00    7.00    --  -11.43 -99.00-180.00   33
  2  ω    -87.00  21.00   1.00    7.00    --  -11.43 -19.00-150.00  108
  3  ω     -8.00  46.00   1.00    7.00    --   11.74 -99.00 120.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0277150000
_diffrn_orient_matrix_UB_12      0.0496474000
_diffrn_orient_matrix_UB_13      0.0062835000
_diffrn_orient_matrix_UB_21      0.0418699000
_diffrn_orient_matrix_UB_22      -0.0282960000
_diffrn_orient_matrix_UB_23      0.0242837000
_diffrn_orient_matrix_UB_31      0.0187627000
_diffrn_orient_matrix_UB_32      -0.0102421000
_diffrn_orient_matrix_UB_33      -0.0366849000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3124
_reflns_number_total             4658
_reflns_odcompleteness_completeness 99.93
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         4658
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0919
_refine_ls_R_factor_gt           0.0567
_refine_ls_restrained_S_all      1.054
_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)+(0.0328P)²+0.9215P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1236
_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:
 C18(H18), C29(H29)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C7(H7), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C27(H27), C28(H28)
2.d Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C31(H31A,H31B,H31C)
;
_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
F1 F -0.07584(12) 0.54708(14) 0.32620(10) 0.0691(5) Uani 1 1 d . . . . .
O1 O 0.36375(14) 0.45560(15) 0.59852(12) 0.0593(5) Uani 1 1 d . . . . .
N1 N 0.23800(15) 0.53732(16) 0.49940(12) 0.0434(5) Uani 1 1 d . . . . .
N2 N 0.32675(14) 0.80822(15) 0.45949(11) 0.0366(5) Uani 1 1 d . . . . .
N3 N 0.26929(16) 0.98679(16) 0.43543(13) 0.0479(6) Uani 1 1 d . . . . .
N4 N 0.17907(17) 1.08623(17) 0.52444(15) 0.0567(6) Uani 1 1 d . . . . .
N5 N 0.22623(17) 0.81998(17) 0.61403(14) 0.0535(6) Uani 1 1 d . . . . .
N6 N 0.15439(15) 0.97697(17) 0.64297(13) 0.0468(6) Uani 1 1 d . . . . .
C1 C 0.08584(18) 0.5340(2) 0.41387(15) 0.0407(6) Uani 1 1 d . . . . .
C2 C -0.0063(2) 0.4870(2) 0.37987(16) 0.0490(7) Uani 1 1 d . . . . .
C3 C -0.0297(2) 0.3822(2) 0.40021(17) 0.0560(8) Uani 1 1 d . . . . .
H3 H -0.092795 0.352466 0.377693 0.067 Uiso 1 1 calc R U . . .
C4 C 0.0421(2) 0.3214(2) 0.45466(17) 0.0546(7) Uani 1 1 d . . . . .
H4 H 0.026721 0.249841 0.466956 0.066 Uiso 1 1 calc R U . . .
C5 C 0.1356(2) 0.3635(2) 0.49121(16) 0.0488(7) Uani 1 1 d . . . . .
H5 H 0.183509 0.322020 0.527388 0.059 Uiso 1 1 calc R U . . .
C6 C 0.15418(18) 0.4699(2) 0.47138(15) 0.0415(6) Uani 1 1 d . . . . .
C7 C 0.13109(18) 0.6400(2) 0.40753(15) 0.0420(6) Uani 1 1 d . . . . .
H7 H 0.102817 0.697921 0.373611 0.050 Uiso 1 1 calc R U . . .
C8 C 0.22212(18) 0.63857(19) 0.46024(15) 0.0390(6) Uani 1 1 d . . . . .
C9 C 0.31297(18) 0.70258(18) 0.49094(14) 0.0368(6) Uani 1 1 d . . . . .
C10 C 0.37912(18) 0.64249(19) 0.54683(14) 0.0377(6) Uani 1 1 d . . . . .
C11 C 0.33195(19) 0.5327(2) 0.55438(15) 0.0419(6) Uani 1 1 d . . . . .
C12 C 0.47948(18) 0.6714(2) 0.59589(15) 0.0416(6) Uani 1 1 d . . . . .
C13 C 0.4990(2) 0.7757(2) 0.62916(16) 0.0501(7) Uani 1 1 d . . . . .
H13 H 0.447722 0.827635 0.621408 0.060 Uiso 1 1 calc R U . . .
C14 C 0.5939(2) 0.8024(3) 0.67349(18) 0.0650(8) Uani 1 1 d . . . . .
H14 H 0.606632 0.872714 0.695057 0.078 Uiso 1 1 calc R U . . .
C15 C 0.6701(2) 0.7261(3) 0.6861(2) 0.0727(9) Uani 1 1 d . . . . .
H15 H 0.734175 0.744817 0.715981 0.087 Uiso 1 1 calc R U . . .
C16 C 0.6518(2) 0.6227(3) 0.6550(2) 0.0746(9) Uani 1 1 d . . . . .
H16 H 0.703229 0.570912 0.664199 0.089 Uiso 1 1 calc R U . . .
C17 C 0.5571(2) 0.5949(2) 0.60982(18) 0.0607(8) Uani 1 1 d . . . . .
H17 H 0.545179 0.524395 0.588546 0.073 Uiso 1 1 calc R U . . .
C18 C 0.38440(17) 0.82128(19) 0.39095(14) 0.0383(6) Uani 1 1 d . . . . .
H18 H 0.340852 0.860526 0.344691 0.046 Uiso 1 1 calc R U . . .
C19 C 0.47828(19) 0.8894(2) 0.42020(16) 0.0527(7) Uani 1 1 d . . . . .
H19A H 0.522027 0.853205 0.467062 0.063 Uiso 1 1 calc R U . . .
H19B H 0.459487 0.960043 0.439346 0.063 Uiso 1 1 calc R U . . .
C20 C 0.5352(2) 0.9061(2) 0.35024(18) 0.0601(8) Uani 1 1 d . . . . .
H20A H 0.493990 0.948648 0.305661 0.072 Uiso 1 1 calc R U . . .
H20B H 0.596808 0.946794 0.371539 0.072 Uiso 1 1 calc R U . . .
C21 C 0.5613(2) 0.7979(2) 0.31577(18) 0.0573(8) Uani 1 1 d . . . . .
H21A H 0.593755 0.810651 0.269058 0.069 Uiso 1 1 calc R U . . .
H21B H 0.608439 0.758659 0.358736 0.069 Uiso 1 1 calc R U . . .
C22 C 0.4682(2) 0.7296(2) 0.28701(17) 0.0587(8) Uani 1 1 d . . . . .
H22A H 0.487240 0.659129 0.267719 0.070 Uiso 1 1 calc R U . . .
H22B H 0.424055 0.765599 0.240258 0.070 Uiso 1 1 calc R U . . .
C23 C 0.4112(2) 0.7121(2) 0.35751(16) 0.0483(7) Uani 1 1 d . . . . .
H23A H 0.349933 0.670624 0.336509 0.058 Uiso 1 1 calc R U . . .
H23B H 0.452887 0.670364 0.402371 0.058 Uiso 1 1 calc R U . . .
C24 C 0.27426(17) 0.89572(19) 0.48142(14) 0.0362(6) Uani 1 1 d . . . . .
C25 C 0.22957(17) 0.89641(19) 0.55198(14) 0.0367(6) Uani 1 1 d . . . . .
C26 C 0.18568(18) 0.9935(2) 0.56931(15) 0.0412(6) Uani 1 1 d . . . . .
C27 C 0.2225(2) 1.0742(2) 0.45938(18) 0.0625(8) Uani 1 1 d . . . . .
H27 H 0.220075 1.135474 0.425261 0.075 Uiso 1 1 calc R U . . .
C28 C 0.1823(2) 0.8731(2) 0.66585(18) 0.0580(8) Uani 1 1 d . . . . .
H28 H 0.170998 0.841786 0.714982 0.070 Uiso 1 1 calc R U . . .
C29 C 0.1038(2) 1.0529(2) 0.69110(18) 0.0575(8) Uani 1 1 d . . . . .
H29 H 0.097893 1.013600 0.742159 0.069 Uiso 1 1 calc R U . . .
C30 C 0.0000(2) 1.0754(3) 0.6461(2) 0.0999(13) Uani 1 1 d . . . . .
H30A H 0.001389 1.121360 0.598666 0.150 Uiso 1 1 calc R U . . .
H30B H -0.036100 1.111892 0.682911 0.150 Uiso 1 1 calc R U . . .
H30C H -0.033277 1.007760 0.627338 0.150 Uiso 1 1 calc R U . . .
C31 C 0.1673(3) 1.1501(3) 0.7191(2) 0.1119(15) Uani 1 1 d . . . . .
H31A H 0.232456 1.126841 0.749669 0.168 Uiso 1 1 calc R U . . .
H31B H 0.135439 1.194377 0.754691 0.168 Uiso 1 1 calc R U . . .
H31C H 0.175221 1.192060 0.671229 0.168 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
F1 C2 1.358(3) . ?
O1 C11 1.208(3) . ?
N1 C6 1.399(3) . ?
N1 C8 1.388(3) . ?
N1 C11 1.395(3) . ?
N2 C9 1.416(3) . ?
N2 C18 1.502(3) . ?
N2 C24 1.372(3) . ?
N3 C24 1.336(3) . ?
N3 C27 1.341(3) . ?
N4 C26 1.342(3) . ?
N4 C27 1.326(3) . ?
N5 C25 1.386(3) . ?
N5 C28 1.305(3) . ?
N6 C26 1.372(3) . ?
N6 C28 1.354(3) . ?
N6 C29 1.474(3) . ?
C1 C2 1.380(3) . ?
C1 C6 1.409(3) . ?
C1 C7 1.445(3) . ?
C2 C3 1.376(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.386(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.380(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.376(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.346(3) . ?
C8 C9 1.455(3) . ?
C9 C10 1.353(3) . ?
C10 C11 1.502(3) . ?
C10 C12 1.468(3) . ?
C12 C13 1.388(3) . ?
C12 C17 1.389(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.374(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.373(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.364(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.380(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9800 . ?
C18 C19 1.510(3) . ?
C18 C23 1.514(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.521(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.507(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.502(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.530(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.410(3) . ?
C25 C26 1.382(3) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C29 H29 0.9800 . ?
C29 C30 1.469(4) . ?
C29 C31 1.481(4) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 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
C8 N1 C6 109.7(2) . . ?
C8 N1 C11 111.4(2) . . ?
C11 N1 C6 138.9(2) . . ?
C9 N2 C18 119.74(17) . . ?
C24 N2 C9 120.02(17) . . ?
C24 N2 C18 119.39(18) . . ?
C24 N3 C27 118.0(2) . . ?
C27 N4 C26 110.7(2) . . ?
C28 N5 C25 103.2(2) . . ?
C26 N6 C29 129.7(2) . . ?
C28 N6 C26 105.08(19) . . ?
C28 N6 C29 125.2(2) . . ?
C2 C1 C6 116.6(2) . . ?
C2 C1 C7 134.9(2) . . ?
C6 C1 C7 108.5(2) . . ?
F1 C2 C1 118.6(2) . . ?
F1 C2 C3 119.7(3) . . ?
C3 C2 C1 121.6(3) . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.2(3) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 118.9 . . ?
C5 C4 C3 122.2(3) . . ?
C5 C4 H4 118.9 . . ?
C4 C5 H5 121.7 . . ?
C6 C5 C4 116.5(3) . . ?
C6 C5 H5 121.7 . . ?
N1 C6 C1 105.3(2) . . ?
C5 C6 N1 131.0(2) . . ?
C5 C6 C1 123.7(2) . . ?
C1 C7 H7 126.6 . . ?
C8 C7 C1 106.7(2) . . ?
C8 C7 H7 126.6 . . ?
N1 C8 C9 106.4(2) . . ?
C7 C8 N1 109.8(2) . . ?
C7 C8 C9 143.8(2) . . ?
N2 C9 C8 122.1(2) . . ?
C10 C9 N2 128.3(2) . . ?
C10 C9 C8 109.4(2) . . ?
C9 C10 C11 107.9(2) . . ?
C9 C10 C12 130.0(2) . . ?
C12 C10 C11 122.1(2) . . ?
O1 C11 N1 125.3(2) . . ?
O1 C11 C10 129.8(2) . . ?
N1 C11 C10 104.9(2) . . ?
C13 C12 C10 120.9(2) . . ?
C13 C12 C17 118.5(3) . . ?
C17 C12 C10 120.6(2) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.3(3) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.4(3) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.1(3) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.2(3) . . ?
C17 C16 H16 119.9 . . ?
C12 C17 H17 119.8 . . ?
C16 C17 C12 120.5(3) . . ?
C16 C17 H17 119.8 . . ?
N2 C18 H18 107.7 . . ?
N2 C18 C19 110.96(18) . . ?
N2 C18 C23 112.12(19) . . ?
C19 C18 H18 107.7 . . ?
C19 C18 C23 110.5(2) . . ?
C23 C18 H18 107.7 . . ?
C18 C19 H19A 109.4 . . ?
C18 C19 H19B 109.4 . . ?
C18 C19 C20 111.3(2) . . ?
H19A C19 H19B 108.0 . . ?
C20 C19 H19A 109.4 . . ?
C20 C19 H19B 109.4 . . ?
C19 C20 H20A 109.4 . . ?
C19 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
C21 C20 C19 111.0(2) . . ?
C21 C20 H20A 109.4 . . ?
C21 C20 H20B 109.4 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 108.0 . . ?
C22 C21 C20 110.9(2) . . ?
C22 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
C21 C22 H22A 109.3 . . ?
C21 C22 H22B 109.3 . . ?
C21 C22 C23 111.4(2) . . ?
H22A C22 H22B 108.0 . . ?
C23 C22 H22A 109.3 . . ?
C23 C22 H22B 109.3 . . ?
C18 C23 C22 110.2(2) . . ?
C18 C23 H23A 109.6 . . ?
C18 C23 H23B 109.6 . . ?
C22 C23 H23A 109.6 . . ?
C22 C23 H23B 109.6 . . ?
H23A C23 H23B 108.1 . . ?
N2 C24 C25 123.6(2) . . ?
N3 C24 N2 117.99(19) . . ?
N3 C24 C25 118.4(2) . . ?
N5 C25 C24 132.8(2) . . ?
C26 C25 N5 110.3(2) . . ?
C26 C25 C24 116.7(2) . . ?
N4 C26 N6 127.3(2) . . ?
N4 C26 C25 126.5(2) . . ?
N6 C26 C25 106.2(2) . . ?
N3 C27 H27 115.2 . . ?
N4 C27 N3 129.7(2) . . ?
N4 C27 H27 115.2 . . ?
N5 C28 N6 115.2(2) . . ?
N5 C28 H28 122.4 . . ?
N6 C28 H28 122.4 . . ?
N6 C29 H29 106.0 . . ?
N6 C29 C31 111.4(2) . . ?
C30 C29 N6 110.8(2) . . ?
C30 C29 H29 106.0 . . ?
C30 C29 C31 115.9(3) . . ?
C31 C29 H29 106.0 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C29 C31 H31A 109.5 . . ?
C29 C31 H31B 109.5 . . ?
C29 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 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
F1 C2 C3 C4 179.6(2) . . . . ?
N1 C8 C9 N2 175.16(19) . . . . ?
N1 C8 C9 C10 -0.9(2) . . . . ?
N2 C9 C10 C11 -175.4(2) . . . . ?
N2 C9 C10 C12 5.7(4) . . . . ?
N2 C18 C19 C20 -178.1(2) . . . . ?
N2 C18 C23 C22 179.1(2) . . . . ?
N2 C24 C25 N5 1.1(4) . . . . ?
N2 C24 C25 C26 175.3(2) . . . . ?
N3 C24 C25 N5 -175.8(2) . . . . ?
N3 C24 C25 C26 -1.5(3) . . . . ?
N5 C25 C26 N4 177.4(2) . . . . ?
N5 C25 C26 N6 -0.2(3) . . . . ?
C1 C2 C3 C4 -1.6(4) . . . . ?
C1 C7 C8 N1 0.5(3) . . . . ?
C1 C7 C8 C9 178.2(3) . . . . ?
C2 C1 C6 N1 -177.0(2) . . . . ?
C2 C1 C6 C5 3.4(3) . . . . ?
C2 C1 C7 C8 176.3(3) . . . . ?
C2 C3 C4 C5 1.8(4) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C4 C5 C6 N1 177.3(2) . . . . ?
C4 C5 C6 C1 -3.2(4) . . . . ?
C6 N1 C8 C7 -0.1(3) . . . . ?
C6 N1 C8 C9 -178.66(17) . . . . ?
C6 N1 C11 O1 -2.7(4) . . . . ?
C6 N1 C11 C10 178.8(2) . . . . ?
C6 C1 C2 F1 177.9(2) . . . . ?
C6 C1 C2 C3 -0.9(3) . . . . ?
C6 C1 C7 C8 -0.8(3) . . . . ?
C7 C1 C2 F1 1.0(4) . . . . ?
C7 C1 C2 C3 -177.8(2) . . . . ?
C7 C1 C6 N1 0.7(2) . . . . ?
C7 C1 C6 C5 -178.9(2) . . . . ?
C7 C8 C9 N2 -2.6(5) . . . . ?
C7 C8 C9 C10 -178.7(3) . . . . ?
C8 N1 C6 C1 -0.4(2) . . . . ?
C8 N1 C6 C5 179.2(2) . . . . ?
C8 N1 C11 O1 177.5(2) . . . . ?
C8 N1 C11 C10 -1.0(2) . . . . ?
C8 C9 C10 C11 0.3(2) . . . . ?
C8 C9 C10 C12 -178.6(2) . . . . ?
C9 N2 C18 C19 -117.7(2) . . . . ?
C9 N2 C18 C23 6.4(3) . . . . ?
C9 N2 C24 N3 -163.5(2) . . . . ?
C9 N2 C24 C25 19.6(3) . . . . ?
C9 C10 C11 O1 -178.0(2) . . . . ?
C9 C10 C11 N1 0.4(2) . . . . ?
C9 C10 C12 C13 37.9(4) . . . . ?
C9 C10 C12 C17 -141.9(3) . . . . ?
C10 C12 C13 C14 -178.6(2) . . . . ?
C10 C12 C17 C16 179.1(3) . . . . ?
C11 N1 C6 C1 179.8(3) . . . . ?
C11 N1 C6 C5 -0.6(5) . . . . ?
C11 N1 C8 C7 179.77(19) . . . . ?
C11 N1 C8 C9 1.2(2) . . . . ?
C11 C10 C12 C13 -140.9(2) . . . . ?
C11 C10 C12 C17 39.3(3) . . . . ?
C12 C10 C11 O1 1.0(4) . . . . ?
C12 C10 C11 N1 179.39(19) . . . . ?
C12 C13 C14 C15 -0.7(4) . . . . ?
C13 C12 C17 C16 -0.7(4) . . . . ?
C13 C14 C15 C16 -0.3(5) . . . . ?
C14 C15 C16 C17 0.8(5) . . . . ?
C15 C16 C17 C12 -0.3(5) . . . . ?
C17 C12 C13 C14 1.2(4) . . . . ?
C18 N2 C9 C8 -95.5(2) . . . . ?
C18 N2 C9 C10 79.7(3) . . . . ?
C18 N2 C24 N3 5.9(3) . . . . ?
C18 N2 C24 C25 -171.0(2) . . . . ?
C18 C19 C20 C21 -56.2(3) . . . . ?
C19 C18 C23 C22 -56.6(3) . . . . ?
C19 C20 C21 C22 55.6(3) . . . . ?
C20 C21 C22 C23 -56.2(3) . . . . ?
C21 C22 C23 C18 56.7(3) . . . . ?
C23 C18 C19 C20 56.8(3) . . . . ?
C24 N2 C9 C8 73.9(3) . . . . ?
C24 N2 C9 C10 -110.9(3) . . . . ?
C24 N2 C18 C19 72.9(3) . . . . ?
C24 N2 C18 C23 -163.0(2) . . . . ?
C24 N3 C27 N4 0.7(5) . . . . ?
C24 C25 C26 N4 1.9(4) . . . . ?
C24 C25 C26 N6 -175.7(2) . . . . ?
C25 N5 C28 N6 1.3(3) . . . . ?
C26 N4 C27 N3 -0.5(5) . . . . ?
C26 N6 C28 N5 -1.4(3) . . . . ?
C26 N6 C29 C30 69.4(4) . . . . ?
C26 N6 C29 C31 -61.1(4) . . . . ?
C27 N3 C24 N2 -176.6(2) . . . . ?
C27 N3 C24 C25 0.4(4) . . . . ?
C27 N4 C26 N6 176.2(3) . . . . ?
C27 N4 C26 C25 -0.9(4) . . . . ?
C28 N5 C25 C24 173.9(3) . . . . ?
C28 N5 C25 C26 -0.6(3) . . . . ?
C28 N6 C26 N4 -176.7(3) . . . . ?
C28 N6 C26 C25 0.9(3) . . . . ?
C28 N6 C29 C30 -112.4(3) . . . . ?
C28 N6 C29 C31 117.0(3) . . . . ?
C29 N6 C26 N4 1.8(4) . . . . ?
C29 N6 C26 C25 179.3(2) . . . . ?
C29 N6 C28 N5 -179.9(2) . . . . ?

_olex2_date_sample_data_collection 2019-12-20
_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 1.105
_oxdiff_exptl_absorpt_empirical_full_min 0.902
####################################################################### 
# 
# 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_s6-2
_database_code_depnum_ccdc_archive 'CCDC 1992409'
loop_
_audit_author_name
_audit_author_address
'Xu Zhongnan'
;Guangzhou Medical University, Xinzao Town, Panyu District, Guangzhou City, Guangdong Province
China
;
_audit_update_record             
;
2020-03-30 deposited with the CCDC.	2020-10-19 downloaded from the CCDC.
;
_audit_creation_date             2020-03-23
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H14 Mn N5 O4'
_chemical_formula_sum            'C20 H14 Mn N5 O4'
_chemical_formula_weight         443.30
_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'
Mn Mn 0.3368 0.7283 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   23.612(6)
_cell_length_b                   6.3254(14)
_cell_length_c                   25.263(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.31(3)
_cell_angle_gamma                90
_cell_volume                     3742.6(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1312
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      24.1410
_cell_measurement_theta_min      3.2620
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.745
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.573
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1808
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0721
_diffrn_reflns_av_unetI/netI     0.0876
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            11051
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.224
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -28.00  63.00   1.00    6.50    --  -11.90  37.00  60.00   91
  2  ω    -36.00  52.00   1.00    6.50    --  -11.90  37.00 -30.00   88
  3  ω    -17.00  29.00   1.00    6.50    --  -11.90 -99.00  60.00   46
  4  ω    -18.00   7.00   1.00    6.50    --  -11.90-100.00 -24.00   25
  5  ω     41.00  66.00   1.00    6.50    --   12.05-178.00 -60.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0146469500
_diffrn_orient_matrix_UB_12      -0.0435351500
_diffrn_orient_matrix_UB_13      0.0237208000
_diffrn_orient_matrix_UB_21      -0.0249383500
_diffrn_orient_matrix_UB_22      0.0112683500
_diffrn_orient_matrix_UB_23      0.0127222000
_diffrn_orient_matrix_UB_31      -0.0089399000
_diffrn_orient_matrix_UB_32      -0.1026642000
_diffrn_orient_matrix_UB_33      -0.0086499000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2364
_reflns_number_total             3249
_reflns_odcompleteness_completeness 98.12
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3249
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0491
_refine_ls_restrained_S_all      1.090
_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)+(0.0195P)²+3.7469P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0858
_refine_ls_wR_factor_ref         0.1026
_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.a Ternary CH refined with riding coordinates:
 C14(H14)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C11(H11), C13(H13)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_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
Mn1 Mn 0.49089(2) 0.45290(8) 0.35642(2) 0.01318(17) Uani 1 1 d . . . . .
O1 O 0.54384(12) 0.6263(4) 0.46127(11) 0.0260(7) Uani 1 1 d . . . . .
O2 O 0.58584(11) 0.1476(4) 0.36438(10) 0.0225(6) Uani 1 1 d . . . . .
O3 O 0.55064(11) 0.7585(4) 0.29287(10) 0.0233(7) Uani 1 1 d . . . . .
O4 O 0.43261(12) 0.2196(4) 0.26152(11) 0.0244(7) Uani 1 1 d . . . . .
N1 N 0.39385(12) 0.3192(4) 0.40738(11) 0.0133(7) Uani 1 1 d . . . . .
N2 N 0.26796(12) 0.5278(4) 0.39435(12) 0.0161(7) Uani 1 1 d . . . . .
N3 N 0.25680(12) 0.8430(4) 0.35330(12) 0.0160(7) Uani 1 1 d . . . . .
N4 N 0.35172(13) 0.8945(4) 0.32910(12) 0.0140(7) Uani 1 1 d . . . . .
N5 N 0.41408(12) 0.6064(4) 0.35824(11) 0.0130(7) Uani 1 1 d . . . . .
C1 C 0.36964(15) 0.1681(5) 0.44008(14) 0.0133(8) Uani 1 1 d . . . . .
C2 C 0.31697(16) 0.1564(6) 0.45845(14) 0.0168(9) Uani 1 1 d . . . . .
H2 H 0.289235 0.259551 0.449981 0.020 Uiso 1 1 calc R U . . .
C3 C 0.30729(16) -0.0170(6) 0.49022(15) 0.0193(9) Uani 1 1 d . . . . .
H3 H 0.272375 -0.029027 0.503344 0.023 Uiso 1 1 calc R U . . .
C4 C 0.34864(15) -0.1728(5) 0.50283(14) 0.0158(9) Uani 1 1 d . . . . .
H4 H 0.340599 -0.288641 0.523271 0.019 Uiso 1 1 calc R U . . .
C5 C 0.40129(16) -0.1560(5) 0.48518(14) 0.0173(9) Uani 1 1 d . . . . .
H5 H 0.429105 -0.258491 0.494106 0.021 Uiso 1 1 calc R U . . .
C6 C 0.41240(15) 0.0177(5) 0.45357(14) 0.0123(8) Uani 1 1 d . . . . .
C7 C 0.46168(15) 0.0767(5) 0.42945(14) 0.0129(8) Uani 1 1 d . . . . .
H7 H 0.495955 0.002572 0.432614 0.016 Uiso 1 1 calc R U . . .
C8 C 0.45070(14) 0.2566(5) 0.40140(14) 0.0126(8) Uani 1 1 d . . . . .
C9 C 0.37379(15) 0.5015(5) 0.38272(14) 0.0124(8) Uani 1 1 d . . . . .
C10 C 0.31945(15) 0.5902(5) 0.37828(14) 0.0132(8) Uani 1 1 d . . . . .
C11 C 0.23262(16) 0.6815(6) 0.37849(15) 0.0185(9) Uani 1 1 d . . . . .
H11 H 0.194390 0.680675 0.383895 0.022 Uiso 1 1 calc R U . . .
C12 C 0.31245(15) 0.7857(5) 0.35220(14) 0.0115(8) Uani 1 1 d . . . . .
C13 C 0.40055(15) 0.7934(5) 0.33332(14) 0.0137(8) Uani 1 1 d . . . . .
H13 H 0.429467 0.857545 0.317295 0.016 Uiso 1 1 calc R U . . .
C14 C 0.22975(16) 1.0382(5) 0.32967(16) 0.0219(9) Uani 1 1 d . . . . .
H14 H 0.258665 1.150151 0.332486 0.026 Uiso 1 1 calc R U . . .
C15 C 0.18204(17) 1.1065(6) 0.36101(19) 0.0349(12) Uani 1 1 d . . . . .
H15A H 0.151895 1.003691 0.356505 0.052 Uiso 1 1 calc R U . . .
H15B H 0.167493 1.241242 0.348164 0.052 Uiso 1 1 calc R U . . .
H15C H 0.196587 1.117625 0.398155 0.052 Uiso 1 1 calc R U . . .
C16 C 0.2094(2) 1.0020(7) 0.27120(18) 0.0403(12) Uani 1 1 d . . . . .
H16A H 0.241530 0.973077 0.252621 0.061 Uiso 1 1 calc R U . . .
H16B H 0.189987 1.126150 0.256418 0.061 Uiso 1 1 calc R U . . .
H16C H 0.183626 0.883960 0.267441 0.061 Uiso 1 1 calc R U . . .
C17 C 0.45542(16) 0.3105(6) 0.29744(16) 0.0174(9) Uani 1 1 d . . . . .
C18 C 0.52569(16) 0.6455(6) 0.31701(15) 0.0172(9) Uani 1 1 d . . . . .
C19 C 0.54980(17) 0.2709(6) 0.36041(14) 0.0171(9) Uani 1 1 d . . . . .
C20 C 0.52322(15) 0.5686(5) 0.42087(17) 0.0156(9) 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
Mn1 N5 2.063(3) . ?
Mn1 C8 2.002(3) . ?
Mn1 C17 1.848(4) . ?
Mn1 C18 1.833(4) . ?
Mn1 C19 1.799(4) . ?
Mn1 C20 1.858(4) . ?
O1 C20 1.134(4) . ?
O2 C19 1.149(4) . ?
O3 C18 1.150(4) . ?
O4 C17 1.149(4) . ?
N1 C1 1.429(4) . ?
N1 C8 1.426(4) . ?
N1 C9 1.367(4) . ?
N2 C10 1.387(4) . ?
N2 C11 1.310(4) . ?
N3 C11 1.367(5) . ?
N3 C12 1.367(4) . ?
N3 C14 1.480(4) . ?
N4 C12 1.346(4) . ?
N4 C13 1.311(4) . ?
N5 C9 1.370(4) . ?
N5 C13 1.359(4) . ?
C1 C2 1.384(5) . ?
C1 C6 1.397(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.395(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.395(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.377(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.403(5) . ?
C6 C7 1.430(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.348(5) . ?
C9 C10 1.392(5) . ?
C10 C12 1.401(5) . ?
C11 H11 0.9300 . ?
C13 H13 0.9300 . ?
C14 H14 0.9800 . ?
C14 C15 1.520(5) . ?
C14 C16 1.512(6) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C8 Mn1 N5 78.33(13) . . ?
C17 Mn1 N5 86.43(14) . . ?
C17 Mn1 C8 87.51(15) . . ?
C17 Mn1 C20 172.72(16) . . ?
C18 Mn1 N5 98.95(14) . . ?
C18 Mn1 C8 176.67(15) . . ?
C18 Mn1 C17 94.26(16) . . ?
C18 Mn1 C20 92.95(16) . . ?
C19 Mn1 N5 167.40(14) . . ?
C19 Mn1 C8 89.44(15) . . ?
C19 Mn1 C17 90.06(16) . . ?
C19 Mn1 C18 93.37(16) . . ?
C19 Mn1 C20 88.54(16) . . ?
C20 Mn1 N5 93.41(13) . . ?
C20 Mn1 C8 85.33(15) . . ?
C8 N1 C1 109.1(3) . . ?
C9 N1 C1 133.4(3) . . ?
C9 N1 C8 117.6(3) . . ?
C11 N2 C10 104.3(3) . . ?
C11 N3 C12 105.7(3) . . ?
C11 N3 C14 128.8(3) . . ?
C12 N3 C14 125.4(3) . . ?
C13 N4 C12 111.3(3) . . ?
C9 N5 Mn1 116.4(2) . . ?
C13 N5 Mn1 123.7(2) . . ?
C13 N5 C9 119.6(3) . . ?
C2 C1 N1 132.3(3) . . ?
C2 C1 C6 122.3(3) . . ?
C6 C1 N1 105.5(3) . . ?
C1 C2 H2 121.5 . . ?
C1 C2 C3 117.1(3) . . ?
C3 C2 H2 121.5 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.7(3) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.4 . . ?
C4 C5 C6 119.1(3) . . ?
C6 C5 H5 120.4 . . ?
C1 C6 C5 119.4(3) . . ?
C1 C6 C7 108.7(3) . . ?
C5 C6 C7 131.9(3) . . ?
C6 C7 H7 125.3 . . ?
C8 C7 C6 109.4(3) . . ?
C8 C7 H7 125.3 . . ?
N1 C8 Mn1 114.1(2) . . ?
C7 C8 Mn1 138.5(3) . . ?
C7 C8 N1 107.4(3) . . ?
N1 C9 N5 113.2(3) . . ?
N1 C9 C10 129.8(3) . . ?
N5 C9 C10 117.0(3) . . ?
N2 C10 C9 134.0(3) . . ?
N2 C10 C12 109.5(3) . . ?
C9 C10 C12 116.5(3) . . ?
N2 C11 N3 114.2(3) . . ?
N2 C11 H11 122.9 . . ?
N3 C11 H11 122.9 . . ?
N3 C12 C10 106.3(3) . . ?
N4 C12 N3 126.2(3) . . ?
N4 C12 C10 127.5(3) . . ?
N4 C13 N5 127.9(3) . . ?
N4 C13 H13 116.0 . . ?
N5 C13 H13 116.0 . . ?
N3 C14 H14 108.2 . . ?
N3 C14 C15 109.7(3) . . ?
N3 C14 C16 109.6(3) . . ?
C15 C14 H14 108.2 . . ?
C16 C14 H14 108.2 . . ?
C16 C14 C15 112.8(4) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4 C17 Mn1 178.4(3) . . ?
O3 C18 Mn1 175.6(3) . . ?
O2 C19 Mn1 176.5(3) . . ?
O1 C20 Mn1 175.6(3) . . ?

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
Mn1 N5 C9 N1 6.8(4) . . . . ?
Mn1 N5 C9 C10 -172.0(2) . . . . ?
Mn1 N5 C13 N4 174.7(3) . . . . ?
N1 C1 C2 C3 179.9(3) . . . . ?
N1 C1 C6 C5 -178.9(3) . . . . ?
N1 C1 C6 C7 0.0(4) . . . . ?
N1 C9 C10 N2 -2.7(7) . . . . ?
N1 C9 C10 C12 177.3(3) . . . . ?
N2 C10 C12 N3 1.0(4) . . . . ?
N2 C10 C12 N4 -177.3(3) . . . . ?
N5 C9 C10 N2 175.8(4) . . . . ?
N5 C9 C10 C12 -4.1(5) . . . . ?
C1 N1 C8 Mn1 -180.0(2) . . . . ?
C1 N1 C8 C7 -0.7(4) . . . . ?
C1 N1 C9 N5 175.3(3) . . . . ?
C1 N1 C9 C10 -6.1(6) . . . . ?
C1 C2 C3 C4 -0.3(5) . . . . ?
C1 C6 C7 C8 -0.4(4) . . . . ?
C2 C1 C6 C5 2.4(5) . . . . ?
C2 C1 C6 C7 -178.7(3) . . . . ?
C2 C3 C4 C5 1.8(6) . . . . ?
C3 C4 C5 C6 -1.2(5) . . . . ?
C4 C5 C6 C1 -0.9(5) . . . . ?
C4 C5 C6 C7 -179.5(4) . . . . ?
C5 C6 C7 C8 178.3(4) . . . . ?
C6 C1 C2 C3 -1.8(5) . . . . ?
C6 C7 C8 Mn1 179.7(3) . . . . ?
C6 C7 C8 N1 0.6(4) . . . . ?
C8 N1 C1 C2 178.9(4) . . . . ?
C8 N1 C1 C6 0.4(4) . . . . ?
C8 N1 C9 N5 -4.2(4) . . . . ?
C8 N1 C9 C10 174.4(3) . . . . ?
C9 N1 C1 C2 -0.6(7) . . . . ?
C9 N1 C1 C6 -179.2(3) . . . . ?
C9 N1 C8 Mn1 -0.3(4) . . . . ?
C9 N1 C8 C7 179.0(3) . . . . ?
C9 N5 C13 N4 0.2(5) . . . . ?
C9 C10 C12 N3 -179.1(3) . . . . ?
C9 C10 C12 N4 2.7(5) . . . . ?
C10 N2 C11 N3 -0.5(4) . . . . ?
C11 N2 C10 C9 179.7(4) . . . . ?
C11 N2 C10 C12 -0.3(4) . . . . ?
C11 N3 C12 N4 177.1(3) . . . . ?
C11 N3 C12 C10 -1.2(4) . . . . ?
C11 N3 C14 C15 31.9(5) . . . . ?
C11 N3 C14 C16 -92.5(5) . . . . ?
C12 N3 C11 N2 1.1(4) . . . . ?
C12 N3 C14 C15 -150.7(3) . . . . ?
C12 N3 C14 C16 85.0(4) . . . . ?
C12 N4 C13 N5 -1.8(5) . . . . ?
C13 N4 C12 N3 -177.6(3) . . . . ?
C13 N4 C12 C10 0.3(5) . . . . ?
C13 N5 C9 N1 -178.2(3) . . . . ?
C13 N5 C9 C10 3.0(5) . . . . ?
C14 N3 C11 N2 178.9(3) . . . . ?
C14 N3 C12 N4 -0.8(6) . . . . ?
C14 N3 C12 C10 -179.1(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 1.273
_oxdiff_exptl_absorpt_empirical_full_min 0.639
####################################################################### 
# 
# 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_2-50
_database_code_depnum_ccdc_archive 'CCDC 1992404'
loop_
_audit_author_name
_audit_author_address
'Xu Zhongnan'
;Guangzhou Medical University, Xinzao Town, Panyu District, Guangzhou City, Guangdong Province
China
;
_audit_update_record             
;
2020-03-30 deposited with the CCDC.	2020-10-19 downloaded from the CCDC.
;
_audit_creation_date             2019-03-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H21 N5 O'
_chemical_formula_sum            'C24 H21 N5 O'
_chemical_formula_weight         395.46
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   12.7739(5)
_cell_length_b                   13.0372(6)
_cell_length_c                   13.9428(5)
_cell_angle_alpha                99.281(3)
_cell_angle_beta                 90.056(3)
_cell_angle_gamma                107.625(4)
_cell_volume                     2180.95(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6408
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.0390
_cell_measurement_theta_min      3.2060
_shelx_estimated_absorpt_T_max   0.936
_shelx_estimated_absorpt_T_min   0.919
_exptl_absorpt_coefficient_mu    0.613
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59236
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.204
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0544
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15562
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.522
_diffrn_reflns_theta_min         3.216
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -33.00  25.00   1.00    1.00    --  -40.98  77.00 -60.00   58
  2  ω    -56.00  -9.00   1.00    1.00    --  -40.98 125.00-180.00   47
  3  ω    -66.00  21.00   1.00    1.00    --  -40.98  38.00-150.00   87
  4  ω    -94.00 -60.00   1.00    1.00    --  -40.98 125.00-180.00   34
  5  ω   -115.00 -16.00   1.00    1.00    --  -40.98 -38.00  30.00   99
  6  ω     44.00  97.00   1.00    1.00    --   40.98-125.00   0.00   53
  7  ω     35.00 127.00   1.00    1.00    --  106.95 -45.00  60.00   92
  8  ω     83.00 140.00   1.00    1.00    --  106.95 -77.00 120.00   57
  9  ω     74.00 115.00   1.00    1.00    --  106.95-125.00  60.00   41
 10  ω     71.00 108.00   1.00    1.00    --  106.95 -95.00 120.00   37
 11  ω     33.00 109.00   1.00    1.00    --  106.95 -95.00  60.00   76
 12  ω     79.00 114.00   1.00    1.00    --  106.95-125.00 -60.00   35
 13  ω     42.00  69.00   1.00    1.00    --  106.95-125.00 -60.00   27
 14  ω     28.00  99.00   1.00    1.00    --  106.95 -95.00 -60.00   71
 15  ω     34.00 133.00   1.00    1.00    --  106.95 -45.00 -90.00   99
 16  ω    133.00 178.00   1.00    1.00    --  106.95  61.00-150.00   45
 17  ω     95.00 124.00   1.00    1.00    --  106.95 125.00 -30.00   29
 18  ω     81.00 109.00   1.00    1.00    --  106.95  61.00-150.00   28
 19  ω     54.00 176.00   1.00    1.00    --  106.95  15.00 -60.00  122
 20  ω    119.00 174.00   1.00    1.00    --  106.95  45.00 150.00   55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0087930000
_diffrn_orient_matrix_UB_12      -0.0769827000
_diffrn_orient_matrix_UB_13      -0.0979193000
_diffrn_orient_matrix_UB_21      0.0538217000
_diffrn_orient_matrix_UB_22      0.0990277000
_diffrn_orient_matrix_UB_23      -0.0497667000
_diffrn_orient_matrix_UB_31      0.1143848000
_diffrn_orient_matrix_UB_32      -0.0097307000
_diffrn_orient_matrix_UB_33      0.0224678000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6975
_reflns_number_total             8529
_reflns_odcompleteness_completeness 99.81
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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         0.548
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     545
_refine_ls_number_reflns         8529
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0616
_refine_ls_restrained_S_all      1.066
_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)+(0.0696P)²+2.2542P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1657
_refine_ls_wR_factor_ref         0.1742
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(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:
 c10B(H10B), c10(H10), c22(H22), c22B(H22B)
2.b Aromatic/amide H refined with riding coordinates:
 N1B(H1B), N1(H1), c1B(H1Ba), c1(H1a), c3B(H3B), c18(H18), c21(H21), c4B(H4B),
 c6(H6), c3(H3), c16B(H16B), c6B(H6B), c12B(H12B), c18B(H18B), c4(H4), c16(H16),
  c13B(H13B), c5B(H5B), c21B(H21B), c14B(H14B), c5(H5), c12(H12), c15(H15),
 c15B(H15B), c14(H14), c13(H13)
2.c Idealised Me refined as rotating group:
 c24(H24d,H24e,H24f), c23(H23d,H23e,H23f), c23B(H23a,H23b,H23c), c24B(H24a,
 H24b,H24c)
;
_atom_sites_solution_hydrogens   geom
_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
O1B O 0.51493(14) 0.42167(14) 0.08176(12) 0.0266(4) Uani 1 1 d . . . . .
O1 O 1.08372(14) 0.59094(14) 0.40789(13) 0.0289(4) Uani 1 1 d . . . . .
N1B N 0.50378(16) 0.62912(16) 0.15831(13) 0.0205(4) Uani 1 1 d . . . . .
H1B H 0.561109 0.632811 0.125101 0.025 Uiso 1 1 calc R . . . .
N1 N 0.92285(16) 0.39047(16) 0.34077(13) 0.0206(4) Uani 1 1 d . . . . .
H1 H 0.978855 0.380241 0.367297 0.025 Uiso 1 1 calc R . . . .
N2 N 0.90517(16) 0.67073(16) 0.56474(14) 0.0212(4) Uani 1 1 d . . . . .
N3 N 0.73174(16) 0.67174(16) 0.63265(13) 0.0212(4) Uani 1 1 d . . . . .
N5 N 0.60417(15) 0.69428(16) 0.51394(13) 0.0206(4) Uani 1 1 d . . . . .
N2B N 0.28865(16) 0.33405(17) -0.05908(14) 0.0236(4) Uani 1 1 d . . . . .
N4 N 0.71088(16) 0.70264(18) 0.38354(14) 0.0242(4) Uani 1 1 d . . . . .
N3B N 0.11764(17) 0.33797(18) -0.12996(14) 0.0277(5) Uani 1 1 d . . . . .
N4B N -0.01649(16) 0.34787(18) -0.00808(14) 0.0262(5) Uani 1 1 d . . . . .
N5B N 0.08400(17) 0.3471(2) 0.12578(15) 0.0296(5) Uani 1 1 d . . . . .
C20 C 0.76794(18) 0.69065(18) 0.46371(15) 0.0186(4) Uani 1 1 d . . . . .
C19 C 0.70281(18) 0.68470(18) 0.54419(16) 0.0188(4) Uani 1 1 d . . . . .
C17 C 0.87336(18) 0.68416(18) 0.47663(16) 0.0187(4) Uani 1 1 d . . . . .
C2 C 0.76150(19) 0.3615(2) 0.25894(16) 0.0217(5) Uani 1 1 d . . . . .
C1B C 0.34337(19) 0.5601(2) 0.22615(16) 0.0215(5) Uani 1 1 d . . . . .
H1BA H 0.279518 0.511084 0.243330 0.026 Uiso 1 1 calc R . . . .
C8B C 0.42166(18) 0.53467(19) 0.16683(16) 0.0199(5) Uani 1 1 d . . . . .
C8 C 0.90679(19) 0.49067(19) 0.34001(16) 0.0198(4) Uani 1 1 d . . . . .
C7B C 0.47947(19) 0.7161(2) 0.21117(16) 0.0213(5) Uani 1 1 d . . . . .
C9 C 0.99189(19) 0.59157(19) 0.38368(16) 0.0205(5) Uani 1 1 d . . . . .
C7 C 0.83464(19) 0.31028(19) 0.29224(16) 0.0210(5) Uani 1 1 d . . . . .
C9B C 0.43017(19) 0.42896(19) 0.11815(16) 0.0211(5) Uani 1 1 d . . . . .
C17B C 0.25101(19) 0.33605(19) 0.03086(16) 0.0204(5) Uani 1 1 d . . . . .
C1 C 0.80815(18) 0.4750(2) 0.29056(16) 0.0214(5) Uani 1 1 d . . . . .
H1A H 0.777976 0.529025 0.280011 0.026 Uiso 1 1 calc R . . . .
C3B C 0.3379(2) 0.7491(2) 0.31819(18) 0.0263(5) Uani 1 1 d . . . . .
H3B H 0.272724 0.724374 0.349061 0.032 Uiso 1 1 calc R . . . .
C10B C 0.32594(19) 0.33135(19) 0.11409(16) 0.0206(5) Uani 1 1 d . . . . .
H10B H 0.288909 0.341931 0.174731 0.025 Uiso 1 1 calc R . . . .
C2B C 0.37884(19) 0.6751(2) 0.25591(16) 0.0218(5) Uani 1 1 d . . . . .
C10 C 0.95521(18) 0.69403(19) 0.39741(16) 0.0199(5) Uani 1 1 d . . . . .
H10 H 0.915642 0.693179 0.336887 0.024 Uiso 1 1 calc R . . . .
C18 C 0.83406(19) 0.6650(2) 0.63602(16) 0.0230(5) Uani 1 1 d . . . . .
H18 H 0.859194 0.654987 0.695399 0.028 Uiso 1 1 calc R . . . .
C11B C 0.34436(18) 0.22030(19) 0.10353(16) 0.0212(5) Uani 1 1 d . . . . .
C20B C 0.1453(2) 0.3414(2) 0.04410(16) 0.0237(5) Uani 1 1 d . . . . .
C19B C 0.08359(19) 0.3417(2) -0.03918(17) 0.0235(5) Uani 1 1 d . . . . .
C11 C 1.04428(19) 0.80357(19) 0.42030(17) 0.0230(5) Uani 1 1 d . . . . .
C22 C 0.50896(19) 0.6970(2) 0.57255(17) 0.0234(5) Uani 1 1 d . . . . .
H22 H 0.524130 0.683495 0.637482 0.028 Uiso 1 1 calc R . . . .
C21 C 0.6152(2) 0.7043(2) 0.41743(17) 0.0256(5) Uani 1 1 d . . . . .
H21 H 0.559250 0.711609 0.379014 0.031 Uiso 1 1 calc R . . . .
C4B C 0.3959(2) 0.8582(2) 0.33230(18) 0.0290(5) Uani 1 1 d . . . . .
H4B H 0.368987 0.907341 0.372769 0.035 Uiso 1 1 calc R . . . .
C6 C 0.8154(2) 0.1975(2) 0.27129(17) 0.0254(5) Uani 1 1 d . . . . .
H6 H 0.864575 0.164974 0.292691 0.030 Uiso 1 1 calc R . . . .
C3 C 0.66440(19) 0.2960(2) 0.20374(17) 0.0259(5) Uani 1 1 d . . . . .
H3 H 0.614828 0.327433 0.181370 0.031 Uiso 1 1 calc R . . . .
C16B C 0.3044(2) 0.1541(2) 0.17227(18) 0.0264(5) Uani 1 1 d . . . . .
H16B H 0.271169 0.180180 0.226084 0.032 Uiso 1 1 calc R . . . .
C6B C 0.5388(2) 0.8274(2) 0.22639(17) 0.0266(5) Uani 1 1 d . . . . .
H6B H 0.604740 0.853210 0.196947 0.032 Uiso 1 1 calc R . . . .
C12B C 0.3953(2) 0.1801(2) 0.02389(17) 0.0258(5) Uani 1 1 d . . . . .
H12B H 0.424601 0.224126 -0.021841 0.031 Uiso 1 1 calc R . . . .
C18B C 0.2213(2) 0.3347(2) -0.13305(17) 0.0277(5) Uani 1 1 d . . . . .
H18B H 0.250510 0.332540 -0.194152 0.033 Uiso 1 1 calc R . . . .
C4 C 0.6450(2) 0.1853(2) 0.18396(18) 0.0302(6) Uani 1 1 d . . . . .
H4 H 0.581382 0.141490 0.147922 0.036 Uiso 1 1 calc R . . . .
C16 C 1.1302(2) 0.8253(2) 0.48944(18) 0.0272(5) Uani 1 1 d . . . . .
H16 H 1.138187 0.769413 0.519834 0.033 Uiso 1 1 calc R . . . .
C13B C 0.4022(2) 0.0745(2) 0.01273(18) 0.0273(5) Uani 1 1 d . . . . .
H13B H 0.434855 0.047774 -0.041235 0.033 Uiso 1 1 calc R . . . .
C5B C 0.4955(2) 0.8976(2) 0.28696(18) 0.0293(5) Uani 1 1 d . . . . .
H5B H 0.532600 0.972157 0.297968 0.035 Uiso 1 1 calc R . . . .
C21B C -0.0107(2) 0.3502(2) 0.09102(18) 0.0318(6) Uani 1 1 d . . . . .
H21B H -0.068922 0.353718 0.130112 0.038 Uiso 1 1 calc R . . . .
C24 C 0.4066(2) 0.6064(2) 0.5268(2) 0.0333(6) Uani 1 1 d . . . . .
H24D H 0.388981 0.619333 0.463823 0.050 Uiso 1 1 calc GR . . . .
H24E H 0.345961 0.605492 0.567689 0.050 Uiso 1 1 calc GR . . . .
H24F H 0.420416 0.537234 0.520268 0.050 Uiso 1 1 calc GR . . . .
C14B C 0.3610(2) 0.0087(2) 0.08134(19) 0.0282(5) Uani 1 1 d . . . . .
H14B H 0.365311 -0.062143 0.073358 0.034 Uiso 1 1 calc R . . . .
C5 C 0.7193(2) 0.1362(2) 0.21696(19) 0.0303(6) Uani 1 1 d . . . . .
H5 H 0.703529 0.060811 0.201988 0.036 Uiso 1 1 calc R . . . .
C12 C 1.0347(2) 0.8886(2) 0.3754(2) 0.0343(6) Uani 1 1 d . . . . .
H12 H 0.977954 0.875597 0.328784 0.041 Uiso 1 1 calc R . . . .
C15 C 1.2043(2) 0.9296(2) 0.5135(2) 0.0340(6) Uani 1 1 d . . . . .
H15 H 1.261040 0.943171 0.560198 0.041 Uiso 1 1 calc R . . . .
C22B C -0.1122(2) 0.3412(2) -0.07202(18) 0.0299(6) Uani 1 1 d . . . . .
H22B H -0.088747 0.397366 -0.113262 0.036 Uiso 1 1 calc R . . . .
C15B C 0.3134(2) 0.0493(2) 0.16185(19) 0.0308(6) Uani 1 1 d . . . . .
H15B H 0.287291 0.006347 0.209097 0.037 Uiso 1 1 calc R . . . .
C23 C 0.4933(2) 0.8090(2) 0.5835(2) 0.0333(6) Uani 1 1 d . . . . .
H23D H 0.556538 0.862566 0.618083 0.050 Uiso 1 1 calc GR . . . .
H23E H 0.428984 0.808935 0.619191 0.050 Uiso 1 1 calc GR . . . .
H23F H 0.484330 0.826445 0.520330 0.050 Uiso 1 1 calc GR . . . .
C14 C 1.1941(2) 1.0135(2) 0.4685(2) 0.0404(7) Uani 1 1 d . . . . .
H14 H 1.243955 1.083148 0.484393 0.048 Uiso 1 1 calc R . . . .
C23B C -0.1480(2) 0.2319(3) -0.1362(2) 0.0419(7) Uani 1 1 d . . . . .
H23A H -0.090279 0.224851 -0.178412 0.063 Uiso 1 1 calc GR . . . .
H23B H -0.212844 0.225144 -0.174706 0.063 Uiso 1 1 calc GR . . . .
H23C H -0.163751 0.175597 -0.096893 0.063 Uiso 1 1 calc GR . . . .
C13 C 1.1093(3) 0.9929(2) 0.3998(3) 0.0452(8) Uani 1 1 d . . . . .
H13 H 1.101991 1.049055 0.369502 0.054 Uiso 1 1 calc R . . . .
C24B C -0.2052(2) 0.3625(3) -0.0118(2) 0.0389(7) Uani 1 1 d . . . . .
H24A H -0.235386 0.303285 0.022954 0.058 Uiso 1 1 calc GR . . . .
H24B H -0.261701 0.368410 -0.054193 0.058 Uiso 1 1 calc GR . . . .
H24C H -0.177290 0.429382 0.033607 0.058 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1B C9B 1.219(3) . ?
O1 C9 1.223(3) . ?
N1B C8B 1.377(3) . ?
N1B C7B 1.367(3) . ?
N1 C8 1.384(3) . ?
N1 C7 1.370(3) . ?
N2 C17 1.348(3) . ?
N2 C18 1.343(3) . ?
N3 C19 1.338(3) . ?
N3 C18 1.338(3) . ?
N5 C19 1.376(3) . ?
N5 C22 1.472(3) . ?
N5 C21 1.376(3) . ?
N2B C17B 1.343(3) . ?
N2B C18B 1.345(3) . ?
N4 C20 1.389(3) . ?
N4 C21 1.315(3) . ?
N3B C19B 1.337(3) . ?
N3B C18B 1.338(3) . ?
N4B C19B 1.372(3) . ?
N4B C21B 1.379(3) . ?
N4B C22B 1.485(3) . ?
N5B C20B 1.388(3) . ?
N5B C21B 1.318(3) . ?
C20 C19 1.396(3) . ?
C20 C17 1.388(3) . ?
C17 C10 1.515(3) . ?
C2 C7 1.418(3) . ?
C2 C1 1.412(3) . ?
C2 C3 1.416(3) . ?
C1B C8B 1.381(3) . ?
C1B C2B 1.419(3) . ?
C8B C9B 1.470(3) . ?
C8 C9 1.469(3) . ?
C8 C1 1.379(3) . ?
C7B C2B 1.421(3) . ?
C7B C6B 1.400(3) . ?
C9 C10 1.529(3) . ?
C7 C6 1.397(3) . ?
C9B C10B 1.532(3) . ?
C17B C10B 1.524(3) . ?
C17B C20B 1.384(3) . ?
C3B C2B 1.413(3) . ?
C3B C4B 1.371(4) . ?
C10B C11B 1.520(3) . ?
C10 C11 1.518(3) . ?
C11B C16B 1.388(3) . ?
C11B C12B 1.397(3) . ?
C20B C19B 1.404(3) . ?
C11 C16 1.392(4) . ?
C11 C12 1.394(3) . ?
C22 C24 1.528(4) . ?
C22 C23 1.517(3) . ?
C4B C5B 1.411(4) . ?
C6 C5 1.389(3) . ?
C3 C4 1.369(4) . ?
C16B C15B 1.390(4) . ?
C6B C5B 1.384(4) . ?
C12B C13B 1.390(4) . ?
C4 C5 1.407(4) . ?
C16 C15 1.389(4) . ?
C13B C14B 1.386(4) . ?
C14B C15B 1.384(4) . ?
C12 C13 1.392(4) . ?
C15 C14 1.384(4) . ?
C22B C23B 1.494(4) . ?
C22B C24B 1.524(4) . ?
C14 C13 1.378(5) . ?

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
C7B N1B C8B 109.01(19) . . ?
C7 N1 C8 108.64(19) . . ?
C18 N2 C17 118.73(19) . . ?
C18 N3 C19 111.28(19) . . ?
C19 N5 C22 127.71(18) . . ?
C19 N5 C21 104.82(18) . . ?
C21 N5 C22 127.44(19) . . ?
C17B N2B C18B 118.7(2) . . ?
C21 N4 C20 103.26(19) . . ?
C19B N3B C18B 111.3(2) . . ?
C19B N4B C21B 105.31(19) . . ?
C19B N4B C22B 125.5(2) . . ?
C21B N4B C22B 128.9(2) . . ?
C21B N5B C20B 103.75(19) . . ?
N4 C20 C19 110.54(19) . . ?
C17 C20 N4 132.3(2) . . ?
C17 C20 C19 117.2(2) . . ?
N3 C19 N5 127.5(2) . . ?
N3 C19 C20 126.2(2) . . ?
N5 C19 C20 106.35(18) . . ?
N2 C17 C20 118.2(2) . . ?
N2 C17 C10 118.44(19) . . ?
C20 C17 C10 123.30(19) . . ?
C1 C2 C7 107.1(2) . . ?
C1 C2 C3 133.9(2) . . ?
C3 C2 C7 119.0(2) . . ?
C8B C1B C2B 107.0(2) . . ?
N1B C8B C1B 109.4(2) . . ?
N1B C8B C9B 119.5(2) . . ?
C1B C8B C9B 131.1(2) . . ?
N1 C8 C9 120.0(2) . . ?
C1 C8 N1 109.2(2) . . ?
C1 C8 C9 130.7(2) . . ?
N1B C7B C2B 107.8(2) . . ?
N1B C7B C6B 130.0(2) . . ?
C6B C7B C2B 122.1(2) . . ?
O1 C9 C8 121.3(2) . . ?
O1 C9 C10 123.9(2) . . ?
C8 C9 C10 114.75(19) . . ?
N1 C7 C2 107.8(2) . . ?
N1 C7 C6 129.7(2) . . ?
C6 C7 C2 122.4(2) . . ?
O1B C9B C8B 121.1(2) . . ?
O1B C9B C10B 123.1(2) . . ?
C8B C9B C10B 115.8(2) . . ?
N2B C17B C10B 118.7(2) . . ?
N2B C17B C20B 118.6(2) . . ?
C20B C17B C10B 122.6(2) . . ?
C8 C1 C2 107.2(2) . . ?
C4B C3B C2B 118.8(2) . . ?
C17B C10B C9B 106.91(18) . . ?
C11B C10B C9B 115.46(19) . . ?
C11B C10B C17B 111.16(19) . . ?
C1B C2B C7B 106.8(2) . . ?
C3B C2B C1B 134.3(2) . . ?
C3B C2B C7B 118.8(2) . . ?
C17 C10 C9 107.60(18) . . ?
C17 C10 C11 109.64(18) . . ?
C11 C10 C9 117.33(19) . . ?
N3 C18 N2 128.4(2) . . ?
C16B C11B C10B 119.2(2) . . ?
C16B C11B C12B 118.7(2) . . ?
C12B C11B C10B 122.0(2) . . ?
N5B C20B C19B 110.2(2) . . ?
C17B C20B N5B 132.8(2) . . ?
C17B C20B C19B 116.9(2) . . ?
N3B C19B N4B 127.6(2) . . ?
N3B C19B C20B 126.1(2) . . ?
N4B C19B C20B 106.3(2) . . ?
C16 C11 C10 123.0(2) . . ?
C16 C11 C12 118.5(2) . . ?
C12 C11 C10 118.3(2) . . ?
N5 C22 C24 109.91(19) . . ?
N5 C22 C23 110.1(2) . . ?
C23 C22 C24 112.2(2) . . ?
N4 C21 N5 115.0(2) . . ?
C3B C4B C5B 121.7(2) . . ?
C5 C6 C7 116.8(2) . . ?
C4 C3 C2 118.6(2) . . ?
C11B C16B C15B 120.9(2) . . ?
C5B C6B C7B 117.4(2) . . ?
C13B C12B C11B 120.2(2) . . ?
N3B C18B N2B 128.3(2) . . ?
C3 C4 C5 121.5(2) . . ?
C15 C16 C11 120.7(3) . . ?
C14B C13B C12B 120.6(2) . . ?
C6B C5B C4B 121.2(2) . . ?
N5B C21B N4B 114.5(2) . . ?
C15B C14B C13B 119.4(2) . . ?
C6 C5 C4 121.8(2) . . ?
C13 C12 C11 120.5(3) . . ?
C14 C15 C16 120.4(3) . . ?
N4B C22B C23B 109.0(2) . . ?
N4B C22B C24B 110.8(2) . . ?
C23B C22B C24B 111.8(2) . . ?
C14B C15B C16B 120.2(2) . . ?
C13 C14 C15 119.5(3) . . ?
C14 C13 C12 120.5(3) . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 0.000 227.0 54.2 ?
2 0.422 0.521 0.708 8.1 0.0 ?
3 0.578 0.479 0.292 8.1 0.0 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.573
_oxdiff_exptl_absorpt_empirical_full_min 0.553
