# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

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

data_dq_13_2
_database_code_depnum_ccdc_archive 'CCDC 1950828'
loop_
_audit_author_name
_audit_author_address
'Qing-hu Teng'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2019-09-02 deposited with the CCDC.	2019-12-24 downloaded from the CCDC.
;
_audit_creation_date             2018-10-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H23 N3 O2 S'
_chemical_formula_sum            'C18 H23 N3 O2 S'
_chemical_formula_weight         345.45
_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'
S S 0.3331 0.5567 '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                   11.6688(3)
_cell_length_b                   10.6008(3)
_cell_length_c                   31.1741(9)
_cell_angle_alpha                90
_cell_angle_beta                 100.107(3)
_cell_angle_gamma                90
_cell_volume                     3796.35(19)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7412
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4370
_cell_measurement_theta_min      3.8670
_shelx_estimated_absorpt_T_max   0.841
_shelx_estimated_absorpt_T_min   0.816
_exptl_absorpt_coefficient_mu    1.629
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63936
_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    1.209
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.13
_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  0.0356
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            14668
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.752
_diffrn_reflns_theta_min         2.880
_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 0.999
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -11.00  54.00   1.00    1.00    --   41.11 -38.00  90.00   65
  2  ω     41.00  89.00   1.00    1.00    --   41.11-137.00 -48.00   48
  3  ω     26.00 103.00   1.00    1.00    --  106.95 -95.00-150.00   77
  4  ω     87.00 177.00   1.00    1.00    --  106.95  30.00 -60.00   90
  5  ω    116.00 141.00   1.00    1.00    --  106.95 110.00 -59.00   25
  6  ω    102.00 162.00   1.00    1.00    --  106.95 125.00-120.00   60
  7  ω     91.00 178.00   1.00    1.00    --  106.95 133.00-162.00   87
  8  ω    149.00 176.00   1.00    1.00    --  106.95 125.00  60.00   27
  9  ω     98.00 176.00   1.00    1.00    --  106.95 125.00 120.00   78
 10  ω   -114.00  -5.00   1.00    1.00    --  -41.11 -19.00-120.00  109
;
_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      0.0330154000
_diffrn_orient_matrix_UB_12      0.0401355000
_diffrn_orient_matrix_UB_13      0.0480719000
_diffrn_orient_matrix_UB_21      0.0192398000
_diffrn_orient_matrix_UB_22      0.1362731000
_diffrn_orient_matrix_UB_23      -0.0143884000
_diffrn_orient_matrix_UB_31      -0.1285161000
_diffrn_orient_matrix_UB_32      0.0307770000
_diffrn_orient_matrix_UB_33      0.0010462000
_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                6360
_reflns_number_total             7409
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (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         0.519
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         7409
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0564
_refine_ls_restrained_S_all      1.048
_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)+(0.0785P)²+1.4824P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1439
_refine_ls_wR_factor_ref         0.1515
_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. Restrained distances
 C00Y-C0AA
 1.2 with sigma of 0.02
3. Rigid bond restraints
 C00Y, C0AA
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C00Y \\sim C0AA: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004
5. Others
 Sof(S0AB)=1-FVAR(1)
 Sof(S0AA)=FVAR(1)
 Fixed Sof: H0AB(0.5) H0AA(0.5)
6.a Aromatic/amide H refined with riding coordinates:
 N3(H3), N2(H2), N00C(H00C), N00D(H00D), C2(H2A), C4(H4), C3(H3A)
6.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C17(H17A,H17B,H17C), C013(H01A,H01B,H01C), C014(H01D,
 H01E,H01F), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C16(H16A,H16B,H16C),
 C018(H01G,H01H,H01I), C019(H01J,H01K,H01L), C13(H13A,H13B,H13C), C01B(H01M,
 H01N,H01O), C01C(H01P,H01Q,H01R)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 1.02180(5) 1.13367(6) 0.34420(2) 0.03711(16) Uani 1 1 d . . . . .
O2 O 0.77847(12) 0.16606(14) 0.41771(4) 0.0257(3) Uani 1 1 d . . . . .
O1 O 0.81478(12) 0.48733(14) 0.34152(4) 0.0260(3) Uani 1 1 d . . . . .
O006 O 0.38663(12) 0.10452(15) 0.32573(5) 0.0279(3) Uani 1 1 d . . . . .
O007 O 0.42612(12) 0.47376(14) 0.37604(5) 0.0283(3) Uani 1 1 d . . . . .
N3 N 0.82541(14) 0.30618(17) 0.47425(5) 0.0253(4) Uani 1 1 d . . . . .
H3 H 0.849495 0.381871 0.480273 0.030 Uiso 1 1 calc R . . . .
N1 N 0.86892(14) 0.49308(17) 0.41415(5) 0.0246(4) Uani 1 1 d . . . . .
N00A N 0.54699(14) 0.31923(17) 0.40522(5) 0.0253(4) Uani 1 1 d . . . . .
N2 N 0.73583(15) 0.28546(17) 0.32962(5) 0.0283(4) Uani 1 1 d . . . . .
H2 H 0.727864 0.211770 0.340248 0.034 Uiso 1 1 calc R . . . .
N00C N 0.54085(15) 0.06220(17) 0.38069(5) 0.0262(4) Uani 1 1 d . . . . .
H00C H 0.592351 0.098113 0.399937 0.031 Uiso 1 1 calc R . . . .
N00D N 0.30658(15) 0.36742(18) 0.31904(6) 0.0320(4) Uani 1 1 d . . . . .
H00D H 0.298624 0.300596 0.303151 0.038 Uiso 1 1 calc R . . . .
C9 C 0.82269(16) 0.37510(19) 0.40181(6) 0.0225(4) Uani 1 1 d . . . . .
C10 C 0.80710(15) 0.2737(2) 0.43191(6) 0.0223(4) Uani 1 1 d . . . . .
C8 C 0.78822(16) 0.37298(19) 0.35742(6) 0.0233(4) Uani 1 1 d . . . . .
C00H C 0.46803(16) 0.2708(2) 0.37038(6) 0.0229(4) Uani 1 1 d . . . . .
C1 C 0.98571(17) 0.8995(2) 0.35420(6) 0.0245(4) Uani 1 1 d . . . . .
C00J C 0.46211(16) 0.1390(2) 0.35705(6) 0.0236(4) Uani 1 1 d . . . . .
C7 C 0.86313(16) 0.5558(2) 0.37831(6) 0.0248(4) Uani 1 1 d . . . . .
C00L C 0.39462(17) 0.3664(2) 0.35298(6) 0.0242(4) Uani 1 1 d . . . . .
C6 C 0.90097(17) 0.6788(2) 0.37092(7) 0.0271(4) Uani 1 1 d . . . . .
C5 C 0.93598(17) 0.7822(2) 0.36338(6) 0.0255(4) Uani 1 1 d . . . . .
C00O C 0.69714(18) 0.6613(2) 0.50051(7) 0.0282(4) Uani 1 1 d . . . . .
C00P C 0.52077(17) 0.4368(2) 0.40781(7) 0.0257(4) Uani 1 1 d . . . . .
C00Q C 0.54930(18) -0.0761(2) 0.37750(6) 0.0265(4) Uani 1 1 d . . . . .
C00R C 0.57408(17) 0.5259(2) 0.43837(7) 0.0278(4) Uani 1 1 d . . . . .
C00S C 0.62929(18) 0.5886(2) 0.46688(7) 0.0288(4) Uani 1 1 d . . . . .
C15 C 0.69036(18) 0.3023(2) 0.28265(6) 0.0291(5) Uani 1 1 d . . . . .
C11 C 0.80886(18) 0.2265(2) 0.51171(6) 0.0284(4) Uani 1 1 d . . . . .
C2 C 1.09397(17) 0.9094(2) 0.33904(7) 0.0295(4) Uani 1 1 d . . . . .
H2A H 1.139077 0.840220 0.334219 0.035 Uiso 1 1 calc R . . . .
C00W C 0.6521(2) 0.7289(2) 0.53176(7) 0.0344(5) Uani 1 1 d . . . . .
C00X C 0.22173(18) 0.4690(2) 0.30560(7) 0.0302(5) Uani 1 1 d . . . . .
C00Y C 0.81905(19) 0.6712(2) 0.50653(8) 0.0353(5) Uani 1 1 d D U . . .
C18 C 0.7911(2) 0.3219(3) 0.25806(7) 0.0361(5) Uani 1 1 d . . . . .
H18A H 0.833099 0.396745 0.268574 0.054 Uiso 1 1 calc GR . . . .
H18B H 0.761123 0.330697 0.227502 0.054 Uiso 1 1 calc GR . . . .
H18C H 0.842384 0.250467 0.262636 0.054 Uiso 1 1 calc GR . . . .
C4 C 0.93752(18) 1.0152(2) 0.35872(7) 0.0306(5) Uani 1 1 d . . . . .
H4 H 0.867535 1.027724 0.368502 0.037 Uiso 1 1 calc R . . . .
C3 C 1.12401(18) 1.0310(2) 0.33240(7) 0.0346(5) Uani 1 1 d . . . . .
H3A H 1.191719 1.054947 0.322657 0.042 Uiso 1 1 calc R . . . .
C17 C 0.6052(2) 0.4128(3) 0.27505(7) 0.0389(5) Uani 1 1 d . . . . .
H17A H 0.543160 0.399161 0.291082 0.058 Uiso 1 1 calc GR . . . .
H17B H 0.573676 0.419185 0.244547 0.058 Uiso 1 1 calc GR . . . .
H17C H 0.645256 0.489502 0.284764 0.058 Uiso 1 1 calc GR . . . .
C013 C 0.5909(2) -0.1120(2) 0.33562(7) 0.0350(5) Uani 1 1 d . . . . .
H01A H 0.537369 -0.079929 0.311131 0.052 Uiso 1 1 calc GR . . . .
H01B H 0.595033 -0.202199 0.333590 0.052 Uiso 1 1 calc GR . . . .
H01C H 0.666648 -0.076550 0.335686 0.052 Uiso 1 1 calc GR . . . .
C014 C 0.1357(2) 0.4153(2) 0.26744(8) 0.0401(6) Uani 1 1 d . . . . .
H01D H 0.176115 0.394351 0.244103 0.060 Uiso 1 1 calc GR . . . .
H01E H 0.076735 0.476990 0.257526 0.060 Uiso 1 1 calc GR . . . .
H01F H 0.100032 0.340796 0.276671 0.060 Uiso 1 1 calc GR . . . .
C12 C 0.8990(2) 0.1211(3) 0.51820(8) 0.0425(6) Uani 1 1 d . . . . .
H12A H 0.889423 0.069161 0.492584 0.064 Uiso 1 1 calc GR . . . .
H12B H 0.888540 0.070651 0.542810 0.064 Uiso 1 1 calc GR . . . .
H12C H 0.975705 0.156910 0.523302 0.064 Uiso 1 1 calc GR . . . .
C14 C 0.8268(2) 0.3145(3) 0.55104(7) 0.0405(6) Uani 1 1 d . . . . .
H14A H 0.902502 0.352404 0.554247 0.061 Uiso 1 1 calc GR . . . .
H14B H 0.820716 0.267158 0.576807 0.061 Uiso 1 1 calc GR . . . .
H14C H 0.768355 0.379232 0.546832 0.061 Uiso 1 1 calc GR . . . .
C16 C 0.6282(2) 0.1800(3) 0.26751(7) 0.0433(6) Uani 1 1 d . . . . .
H16A H 0.681116 0.110558 0.274127 0.065 Uiso 1 1 calc GR . . . .
H16B H 0.600948 0.183634 0.236633 0.065 Uiso 1 1 calc GR . . . .
H16C H 0.563186 0.168621 0.282206 0.065 Uiso 1 1 calc GR . . . .
C018 C 0.1585(2) 0.5030(3) 0.34284(9) 0.0458(6) Uani 1 1 d . . . . .
H01G H 0.121655 0.429039 0.351919 0.069 Uiso 1 1 calc GR . . . .
H01H H 0.100581 0.565920 0.333158 0.069 Uiso 1 1 calc GR . . . .
H01I H 0.213390 0.535322 0.366883 0.069 Uiso 1 1 calc GR . . . .
C019 C 0.6398(3) -0.1178(2) 0.41630(8) 0.0450(6) Uani 1 1 d . . . . .
H01J H 0.711086 -0.072596 0.416216 0.068 Uiso 1 1 calc GR . . . .
H01K H 0.653682 -0.206649 0.414287 0.068 Uiso 1 1 calc GR . . . .
H01L H 0.611679 -0.100238 0.442832 0.068 Uiso 1 1 calc GR . . . .
C13 C 0.6858(2) 0.1739(3) 0.50484(7) 0.0437(6) Uani 1 1 d . . . . .
H13A H 0.631022 0.242294 0.501467 0.066 Uiso 1 1 calc GR . . . .
H13B H 0.675941 0.123890 0.529591 0.066 Uiso 1 1 calc GR . . . .
H13C H 0.672828 0.122423 0.479114 0.066 Uiso 1 1 calc GR . . . .
C01B C 0.4320(2) -0.1374(3) 0.37887(10) 0.0465(6) Uani 1 1 d . . . . .
H01M H 0.403322 -0.108804 0.404236 0.070 Uiso 1 1 calc GR . . . .
H01N H 0.440862 -0.227413 0.380042 0.070 Uiso 1 1 calc GR . . . .
H01O H 0.377765 -0.114551 0.353198 0.070 Uiso 1 1 calc GR . . . .
C01C C 0.2829(3) 0.5840(3) 0.29062(9) 0.0491(7) Uani 1 1 d . . . . .
H01P H 0.336540 0.617816 0.314772 0.074 Uiso 1 1 calc GR . . . .
H01Q H 0.226112 0.647006 0.279690 0.074 Uiso 1 1 calc GR . . . .
H01R H 0.324511 0.559608 0.267967 0.074 Uiso 1 1 calc GR . . . .
H00W H 0.575(2) 0.732(3) 0.5348(8) 0.034(7) Uiso 1 1 d . . . . .
H00Y H 0.864(2) 0.637(3) 0.4870(9) 0.040(7) Uiso 1 1 d . . . . .
S0AA S 0.74970(7) 0.80135(9) 0.56674(3) 0.0403(3) Uani 0.737(2) 1 d . . P A 1
C0AA C 0.8629(6) 0.7490(8) 0.5434(2) 0.0375(10) Uani 1 1 d D U . . .
S0AB S 0.8854(4) 0.7534(6) 0.55002(16) 0.0273(9) Uani 0.263(2) 1 d . . P A 2
H0AB H 0.956(4) 0.766(4) 0.5536(13) 0.009(10) Uiso 0.5 1 d . . P . .
H0AA H 0.746(5) 0.812(6) 0.596(2) 0.054(17) Uiso 0.5 1 d . . P . .


_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
S1 C4 1.705(2) . ?
S1 C3 1.702(3) . ?
O2 C10 1.248(3) . ?
O1 C8 1.366(2) . ?
O1 C7 1.391(2) . ?
O006 C00J 1.249(2) . ?
O007 C00L 1.361(2) . ?
O007 C00P 1.403(2) . ?
N3 H3 0.8600 . ?
N3 C10 1.344(3) . ?
N3 C11 1.481(3) . ?
N1 C9 1.389(3) . ?
N1 C7 1.292(3) . ?
N00A C00H 1.393(2) . ?
N00A C00P 1.290(3) . ?
N2 H2 0.8600 . ?
N2 C8 1.342(3) . ?
N2 C15 1.478(3) . ?
N00C H00C 0.8600 . ?
N00C C00J 1.346(3) . ?
N00C C00Q 1.474(3) . ?
N00D H00D 0.8600 . ?
N00D C00L 1.339(3) . ?
N00D C00X 1.473(3) . ?
C9 C10 1.459(3) . ?
C9 C8 1.372(3) . ?
C00H C00J 1.455(3) . ?
C00H C00L 1.376(3) . ?
C1 C5 1.422(3) . ?
C1 C2 1.428(3) . ?
C1 C4 1.367(3) . ?
C7 C6 1.408(3) . ?
C6 C5 1.207(3) . ?
C00O C00S 1.424(3) . ?
C00O C00W 1.386(3) . ?
C00O C00Y 1.406(3) . ?
C00P C00R 1.406(3) . ?
C00Q C013 1.519(3) . ?
C00Q C019 1.525(3) . ?
C00Q C01B 1.522(3) . ?
C00R C00S 1.202(3) . ?
C15 C18 1.526(3) . ?
C15 C17 1.528(3) . ?
C15 C16 1.519(3) . ?
C11 C12 1.524(3) . ?
C11 C14 1.525(3) . ?
C11 C13 1.520(3) . ?
C2 H2A 0.9300 . ?
C2 C3 1.362(3) . ?
C00W H00W 0.92(3) . ?
C00W S0AA 1.625(2) . ?
C00X C014 1.526(3) . ?
C00X C018 1.524(3) . ?
C00X C01C 1.528(3) . ?
C00Y H00Y 0.94(3) . ?
C00Y C0AA 1.434(7) . ?
C00Y S0AB 1.682(5) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C4 H4 0.9300 . ?
C3 H3A 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C013 H01A 0.9600 . ?
C013 H01B 0.9600 . ?
C013 H01C 0.9600 . ?
C014 H01D 0.9600 . ?
C014 H01E 0.9600 . ?
C014 H01F 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C018 H01G 0.9600 . ?
C018 H01H 0.9600 . ?
C018 H01I 0.9600 . ?
C019 H01J 0.9600 . ?
C019 H01K 0.9600 . ?
C019 H01L 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C01B H01M 0.9600 . ?
C01B H01N 0.9600 . ?
C01B H01O 0.9600 . ?
C01C H01P 0.9600 . ?
C01C H01Q 0.9600 . ?
C01C H01R 0.9600 . ?
S0AA C0AA 1.709(8) . ?
S0AA H0AA 0.92(7) . ?
C0AA H0AB 1.09(5) . ?
S0AB H0AB 0.82(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
C3 S1 C4 92.59(11) . . ?
C8 O1 C7 104.43(15) . . ?
C00L O007 C00P 104.22(16) . . ?
C10 N3 H3 116.3 . . ?
C10 N3 C11 127.45(18) . . ?
C11 N3 H3 116.3 . . ?
C7 N1 C9 105.37(17) . . ?
C00P N00A C00H 105.88(17) . . ?
C8 N2 H2 116.6 . . ?
C8 N2 C15 126.90(18) . . ?
C15 N2 H2 116.6 . . ?
C00J N00C H00C 116.1 . . ?
C00J N00C C00Q 127.73(17) . . ?
C00Q N00C H00C 116.1 . . ?
C00L N00D H00D 116.0 . . ?
C00L N00D C00X 127.92(18) . . ?
C00X N00D H00D 116.0 . . ?
N1 C9 C10 124.83(18) . . ?
C8 C9 N1 108.96(17) . . ?
C8 C9 C10 126.10(18) . . ?
O2 C10 N3 124.65(19) . . ?
O2 C10 C9 120.08(17) . . ?
N3 C10 C9 115.27(18) . . ?
O1 C8 C9 107.85(17) . . ?
N2 C8 O1 119.08(17) . . ?
N2 C8 C9 133.06(19) . . ?
N00A C00H C00J 124.63(18) . . ?
C00L C00H N00A 108.43(18) . . ?
C00L C00H C00J 126.85(18) . . ?
C5 C1 C2 123.2(2) . . ?
C4 C1 C5 125.03(18) . . ?
C4 C1 C2 111.82(19) . . ?
O006 C00J N00C 124.8(2) . . ?
O006 C00J C00H 119.72(18) . . ?
N00C C00J C00H 115.49(17) . . ?
O1 C7 C6 116.23(17) . . ?
N1 C7 O1 113.37(18) . . ?
N1 C7 C6 130.37(19) . . ?
O007 C00L C00H 108.43(17) . . ?
N00D C00L O007 120.62(18) . . ?
N00D C00L C00H 130.93(19) . . ?
C5 C6 C7 177.3(2) . . ?
C6 C5 C1 175.5(2) . . ?
C00W C00O C00S 124.5(2) . . ?
C00W C00O C00Y 111.5(2) . . ?
C00Y C00O C00S 123.9(2) . . ?
O007 C00P C00R 119.38(18) . . ?
N00A C00P O007 113.04(17) . . ?
N00A C00P C00R 127.57(19) . . ?
N00C C00Q C013 110.00(17) . . ?
N00C C00Q C019 106.24(17) . . ?
N00C C00Q C01B 110.56(18) . . ?
C013 C00Q C019 109.14(19) . . ?
C013 C00Q C01B 110.00(19) . . ?
C01B C00Q C019 110.8(2) . . ?
C00S C00R C00P 171.0(2) . . ?
C00R C00S C00O 178.6(2) . . ?
N2 C15 C18 109.86(17) . . ?
N2 C15 C17 110.89(18) . . ?
N2 C15 C16 105.88(17) . . ?
C18 C15 C17 110.81(19) . . ?
C16 C15 C18 109.15(19) . . ?
C16 C15 C17 110.1(2) . . ?
N3 C11 C12 109.92(17) . . ?
N3 C11 C14 105.48(19) . . ?
N3 C11 C13 110.41(17) . . ?
C12 C11 C14 110.35(19) . . ?
C13 C11 C12 111.2(2) . . ?
C13 C11 C14 109.28(19) . . ?
C1 C2 H2A 123.6 . . ?
C3 C2 C1 112.7(2) . . ?
C3 C2 H2A 123.6 . . ?
C00O C00W H00W 126.2(16) . . ?
C00O C00W S0AA 114.12(17) . . ?
S0AA C00W H00W 119.6(16) . . ?
N00D C00X C014 105.48(19) . . ?
N00D C00X C018 110.34(19) . . ?
N00D C00X C01C 110.11(19) . . ?
C014 C00X C01C 109.8(2) . . ?
C018 C00X C014 110.0(2) . . ?
C018 C00X C01C 111.0(2) . . ?
C00O C00Y H00Y 123.2(17) . . ?
C00O C00Y C0AA 111.1(3) . . ?
C00O C00Y S0AB 117.3(3) . . ?
C0AA C00Y H00Y 125.4(17) . . ?
S0AB C00Y H00Y 119.4(17) . . ?
S0AB C00Y C0AA 6.8(4) . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
S1 C4 H4 124.2 . . ?
C1 C4 S1 111.52(16) . . ?
C1 C4 H4 124.2 . . ?
S1 C3 H3A 124.3 . . ?
C2 C3 S1 111.33(16) . . ?
C2 C3 H3A 124.3 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C00Q C013 H01A 109.5 . . ?
C00Q C013 H01B 109.5 . . ?
C00Q C013 H01C 109.5 . . ?
H01A C013 H01B 109.5 . . ?
H01A C013 H01C 109.5 . . ?
H01B C013 H01C 109.5 . . ?
C00X C014 H01D 109.5 . . ?
C00X C014 H01E 109.5 . . ?
C00X C014 H01F 109.5 . . ?
H01D C014 H01E 109.5 . . ?
H01D C014 H01F 109.5 . . ?
H01E C014 H01F 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
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 . . ?
C00X C018 H01G 109.5 . . ?
C00X C018 H01H 109.5 . . ?
C00X C018 H01I 109.5 . . ?
H01G C018 H01H 109.5 . . ?
H01G C018 H01I 109.5 . . ?
H01H C018 H01I 109.5 . . ?
C00Q C019 H01J 109.5 . . ?
C00Q C019 H01K 109.5 . . ?
C00Q C019 H01L 109.5 . . ?
H01J C019 H01K 109.5 . . ?
H01J C019 H01L 109.5 . . ?
H01K C019 H01L 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C00Q C01B H01M 109.5 . . ?
C00Q C01B H01N 109.5 . . ?
C00Q C01B H01O 109.5 . . ?
H01M C01B H01N 109.5 . . ?
H01M C01B H01O 109.5 . . ?
H01N C01B H01O 109.5 . . ?
C00X C01C H01P 109.5 . . ?
C00X C01C H01Q 109.5 . . ?
C00X C01C H01R 109.5 . . ?
H01P C01C H01Q 109.5 . . ?
H01P C01C H01R 109.5 . . ?
H01Q C01C H01R 109.5 . . ?
C00W S0AA C0AA 93.7(2) . . ?
C00W S0AA H0AA 125(4) . . ?
C0AA S0AA H0AA 129(4) . . ?
C00Y C0AA S0AA 109.5(4) . . ?
C00Y C0AA H0AB 122(2) . . ?
S0AA C0AA H0AB 129(2) . . ?
C00Y S0AB H0AB 120(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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.384
_oxdiff_exptl_absorpt_empirical_full_min 0.724
####################################################################### 
# 
# 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_dq-57
_database_code_depnum_ccdc_archive 'CCDC 1960025'
loop_
_audit_author_name
_audit_author_address
dq
;Jishou University
China
;
_audit_update_record             
;
2019-10-18 deposited with the CCDC.	2019-12-24 downloaded from the CCDC.
;
_audit_creation_date             2019-10-17
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2019.10.11 svn.r3662 for OlexSys, GUI svn.r5962)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H38 N6 O2'
_chemical_formula_sum            'C27 H38 N6 O2'
_chemical_formula_weight         478.63
_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   19.2320(3)
_cell_length_b                   11.92476(17)
_cell_length_c                   23.5435(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5399.40(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5341
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.3710
_cell_measurement_theta_min      3.7440
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.607
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74192
_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    1.178
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2064
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            14096
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.621
_diffrn_reflns_theta_min         3.755
_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 0.999
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      8.00  44.00   1.00    1.00    --   40.98 -99.00  30.00   36
  2  ω     73.00 118.00   1.00    1.50    --  106.95-125.00 150.00   45
  3  ω     87.00 112.00   1.00    1.50    --  106.95-103.00 157.00   25
  4  ω     79.00 145.00   1.00    1.50    --  106.95  30.00 120.00   66
  5  ω    108.00 177.00   1.00    1.50    --  106.95 125.00   0.00   69
  6  ω    151.00 178.00   1.00    1.50    --  106.95  77.00-180.00   27
  7  ω     82.00 147.00   1.00    1.50    --  106.95  77.00-180.00   65
  8  ω     44.00  81.00   1.00    1.00    --   40.98-125.00-120.00   37
  9  ω   -113.00 -16.00   1.00    1.00    --  -40.98 -38.00 150.00   97
;
_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      0.0429992000
_diffrn_orient_matrix_UB_12      -0.0048445000
_diffrn_orient_matrix_UB_13      -0.0551448000
_diffrn_orient_matrix_UB_21      -0.0600507000
_diffrn_orient_matrix_UB_22      -0.0618894000
_diffrn_orient_matrix_UB_23      -0.0298998000
_diffrn_orient_matrix_UB_31      -0.0310125000
_diffrn_orient_matrix_UB_32      0.1132665000
_diffrn_orient_matrix_UB_33      -0.0186667000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\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                4392
_reflns_number_total             5342
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (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 n/a (Sheldrick, 2015)'
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         5342
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0435
_refine_ls_restrained_S_all      1.037
_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)+(0.0551P)²+1.2656P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1067
_refine_ls_wR_factor_ref         0.1146
_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:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C14(H14A,H14B), C18(H18A,H18B), C15(H15A,H15B), C16(H16A,
 H16B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), C7(H7), C11(H11), C8(H8), C9(H9), C10(H10)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C26(H26A,H26B,H26C), C25(H25A,H25B,H25C), C27(H27A,H27B,
 H27C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.62111(5) 0.69953(7) 0.40281(4) 0.0178(2) Uani 1 1 d . . . . .
O1 O 0.46066(5) 0.46930(8) 0.36978(5) 0.0242(2) Uani 1 1 d . . . . .
N2 N 0.62572(6) 0.59003(9) 0.32541(5) 0.0174(2) Uani 1 1 d . . . . .
N4 N 0.77039(6) 0.67300(9) 0.30785(5) 0.0184(2) Uani 1 1 d . . . . .
N6 N 0.82108(6) 0.81920(9) 0.34138(5) 0.0221(3) Uani 1 1 d . . . . .
N1 N 0.52959(6) 0.42071(10) 0.29383(5) 0.0201(3) Uani 1 1 d . . . . .
H1 H 0.568194 0.436357 0.277180 0.024 Uiso 1 1 calc R U . . .
N5 N 0.82988(6) 0.73269(10) 0.30782(6) 0.0231(3) Uani 1 1 d . . . . .
N3 N 0.51953(6) 0.63156(10) 0.44763(5) 0.0229(3) Uani 1 1 d . . . . .
H3 H 0.496405 0.570914 0.453472 0.028 Uiso 1 1 calc R U . . .
C3 C 0.65597(7) 0.66876(10) 0.35346(6) 0.0167(3) Uani 1 1 d . . . . .
C4 C 0.72229(7) 0.72204(10) 0.34234(6) 0.0171(3) Uani 1 1 d . . . . .
C6 C 0.73173(7) 0.90904(11) 0.39981(6) 0.0181(3) Uani 1 1 d . . . . .
C2 C 0.56445(7) 0.63027(10) 0.40393(6) 0.0174(3) Uani 1 1 d . . . . .
C1 C 0.56687(7) 0.56303(11) 0.35671(6) 0.0173(3) Uani 1 1 d . . . . .
C23 C 0.51455(7) 0.47973(11) 0.34088(6) 0.0182(3) Uani 1 1 d . . . . .
C5 C 0.75541(7) 0.81681(11) 0.36339(6) 0.0181(3) Uani 1 1 d . . . . .
C7 C 0.77965(8) 0.96439(11) 0.43448(6) 0.0210(3) Uani 1 1 d . . . . .
H7 H 0.825418 0.939390 0.435995 0.025 Uiso 1 1 calc R U . . .
C24 C 0.48693(8) 0.33216(12) 0.26785(6) 0.0220(3) Uani 1 1 d . . . . .
C11 C 0.66332(8) 0.94853(11) 0.39786(6) 0.0219(3) Uani 1 1 d . . . . .
H11 H 0.630819 0.912785 0.374889 0.026 Uiso 1 1 calc R U . . .
C12 C 0.76410(8) 0.57597(11) 0.27019(6) 0.0212(3) Uani 1 1 d . . . . .
H12A H 0.736547 0.518679 0.288867 0.025 Uiso 1 1 calc R U . . .
H12B H 0.809979 0.545113 0.263206 0.025 Uiso 1 1 calc R U . . .
C8 C 0.75958(8) 1.05635(12) 0.46670(6) 0.0248(3) Uani 1 1 d . . . . .
H8 H 0.791784 1.092250 0.489889 0.030 Uiso 1 1 calc R U . . .
C19 C 0.50550(8) 0.72583(11) 0.48676(6) 0.0218(3) Uani 1 1 d . . . . .
C13 C 0.73032(8) 0.60577(11) 0.21355(6) 0.0219(3) Uani 1 1 d . . . . .
H13 H 0.686955 0.646066 0.221392 0.026 Uiso 1 1 calc R U . . .
C20 C 0.44619(8) 0.68484(12) 0.52431(7) 0.0263(3) Uani 1 1 d . . . . .
H20A H 0.405771 0.671421 0.501373 0.040 Uiso 1 1 calc R U . . .
H20B H 0.435741 0.740748 0.552377 0.040 Uiso 1 1 calc R U . . .
H20C H 0.459705 0.616514 0.542837 0.040 Uiso 1 1 calc R U . . .
C9 C 0.69160(9) 1.09476(12) 0.46435(7) 0.0269(3) Uani 1 1 d . . . . .
H9 H 0.678229 1.156627 0.485776 0.032 Uiso 1 1 calc R U . . .
C10 C 0.64365(8) 1.04077(12) 0.43000(7) 0.0268(3) Uani 1 1 d . . . . .
H10 H 0.598036 1.066470 0.428480 0.032 Uiso 1 1 calc R U . . .
C26 C 0.41507(8) 0.37956(13) 0.25411(8) 0.0309(4) Uani 1 1 d . . . . .
H26A H 0.392496 0.402093 0.288636 0.046 Uiso 1 1 calc R U . . .
H26B H 0.387675 0.323109 0.235553 0.046 Uiso 1 1 calc R U . . .
H26C H 0.419889 0.443277 0.229493 0.046 Uiso 1 1 calc R U . . .
C25 C 0.48120(8) 0.23116(13) 0.30740(7) 0.0286(3) Uani 1 1 d . . . . .
H25A H 0.526900 0.203761 0.316142 0.043 Uiso 1 1 calc R U . . .
H25B H 0.454887 0.173082 0.289090 0.043 Uiso 1 1 calc R U . . .
H25C H 0.458214 0.253121 0.341843 0.043 Uiso 1 1 calc R U . . .
C27 C 0.52447(9) 0.29937(14) 0.21332(7) 0.0311(4) Uani 1 1 d . . . . .
H27A H 0.527819 0.363505 0.188826 0.047 Uiso 1 1 calc R U . . .
H27B H 0.498943 0.241070 0.194450 0.047 Uiso 1 1 calc R U . . .
H27C H 0.570296 0.272868 0.222326 0.047 Uiso 1 1 calc R U . . .
C14 C 0.71239(9) 0.49862(12) 0.18135(7) 0.0302(4) Uani 1 1 d . . . . .
H14A H 0.680156 0.454274 0.203702 0.036 Uiso 1 1 calc R U . . .
H14B H 0.754289 0.454655 0.175842 0.036 Uiso 1 1 calc R U . . .
C21 C 0.56947(9) 0.75093(15) 0.52273(7) 0.0348(4) Uani 1 1 d . . . . .
H21A H 0.582490 0.684967 0.543542 0.052 Uiso 1 1 calc R U . . .
H21B H 0.559095 0.810466 0.548837 0.052 Uiso 1 1 calc R U . . .
H21C H 0.607149 0.773192 0.498473 0.052 Uiso 1 1 calc R U . . .
C18 C 0.77665(10) 0.68137(13) 0.17754(7) 0.0319(4) Uani 1 1 d . . . . .
H18A H 0.820936 0.644561 0.171133 0.038 Uiso 1 1 calc R U . . .
H18B H 0.785456 0.750714 0.197848 0.038 Uiso 1 1 calc R U . . .
C22 C 0.48307(10) 0.82929(13) 0.45282(8) 0.0347(4) Uani 1 1 d . . . . .
H22A H 0.520289 0.852134 0.428228 0.052 Uiso 1 1 calc R U . . .
H22B H 0.472035 0.889230 0.478497 0.052 Uiso 1 1 calc R U . . .
H22C H 0.442850 0.811325 0.430451 0.052 Uiso 1 1 calc R U . . .
C15 C 0.67976(10) 0.52474(14) 0.12351(8) 0.0392(4) Uani 1 1 d . . . . .
H15A H 0.671750 0.455208 0.103156 0.047 Uiso 1 1 calc R U . . .
H15B H 0.635144 0.560968 0.129191 0.047 Uiso 1 1 calc R U . . .
C16 C 0.72603(11) 0.60030(16) 0.08818(7) 0.0409(4) Uani 1 1 d . . . . .
H16A H 0.702843 0.618328 0.052744 0.049 Uiso 1 1 calc R U . . .
H16B H 0.768930 0.561348 0.079226 0.049 Uiso 1 1 calc R U . . .
C17 C 0.74253(12) 0.70801(15) 0.12015(8) 0.0416(4) Uani 1 1 d . . . . .
H17A H 0.700022 0.750048 0.126349 0.050 Uiso 1 1 calc R U . . .
H17B H 0.773670 0.753967 0.097599 0.050 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C3 1.3909(16) . ?
O2 C2 1.3675(16) . ?
O1 C23 1.2460(17) . ?
N2 C3 1.2867(17) . ?
N2 C1 1.3884(17) . ?
N4 N5 1.3474(17) . ?
N4 C4 1.3629(18) . ?
N4 C12 1.4627(17) . ?
N6 N5 1.3104(17) . ?
N6 C5 1.3653(18) . ?
N1 H1 0.8600 . ?
N1 C23 1.3440(18) . ?
N1 C24 1.4705(17) . ?
N3 H3 0.8600 . ?
N3 C2 1.3435(18) . ?
N3 C19 1.4783(18) . ?
C3 C4 1.4486(19) . ?
C4 C5 1.3889(19) . ?
C6 C5 1.4670(19) . ?
C6 C7 1.397(2) . ?
C6 C11 1.398(2) . ?
C2 C1 1.3715(19) . ?
C1 C23 1.4622(19) . ?
C7 H7 0.9300 . ?
C7 C8 1.388(2) . ?
C24 C26 1.528(2) . ?
C24 C25 1.526(2) . ?
C24 C27 1.524(2) . ?
C11 H11 0.9300 . ?
C11 C10 1.388(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.525(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.386(2) . ?
C19 C20 1.523(2) . ?
C19 C21 1.523(2) . ?
C19 C22 1.532(2) . ?
C13 H13 0.9800 . ?
C13 C14 1.5253(19) . ?
C13 C18 1.525(2) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C9 H9 0.9300 . ?
C9 C10 1.385(2) . ?
C10 H10 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.531(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C17 1.535(2) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.515(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.522(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O2 C3 103.94(10) . . ?
C3 N2 C1 105.40(11) . . ?
N5 N4 C4 110.49(11) . . ?
N5 N4 C12 119.20(11) . . ?
C4 N4 C12 130.12(12) . . ?
N5 N6 C5 109.39(11) . . ?
C23 N1 H1 116.6 . . ?
C23 N1 C24 126.79(12) . . ?
C24 N1 H1 116.6 . . ?
N6 N5 N4 107.81(11) . . ?
C2 N3 H3 116.4 . . ?
C2 N3 C19 127.11(12) . . ?
C19 N3 H3 116.4 . . ?
O2 C3 C4 117.36(12) . . ?
N2 C3 O2 113.78(12) . . ?
N2 C3 C4 128.71(13) . . ?
N4 C4 C3 121.14(12) . . ?
N4 C4 C5 104.50(12) . . ?
C5 C4 C3 134.13(13) . . ?
C7 C6 C5 119.39(13) . . ?
C7 C6 C11 118.75(13) . . ?
C11 C6 C5 121.70(13) . . ?
O2 C2 C1 108.08(12) . . ?
N3 C2 O2 121.34(12) . . ?
N3 C2 C1 130.49(13) . . ?
N2 C1 C23 125.69(12) . . ?
C2 C1 N2 108.80(12) . . ?
C2 C1 C23 125.47(13) . . ?
O1 C23 N1 125.23(13) . . ?
O1 C23 C1 120.07(12) . . ?
N1 C23 C1 114.69(12) . . ?
N6 C5 C4 107.81(12) . . ?
N6 C5 C6 119.57(12) . . ?
C4 C5 C6 132.54(13) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.61(14) . . ?
C8 C7 H7 119.7 . . ?
N1 C24 C26 109.10(12) . . ?
N1 C24 C25 110.67(12) . . ?
N1 C24 C27 105.68(12) . . ?
C25 C24 C26 110.85(13) . . ?
C27 C24 C26 110.19(13) . . ?
C27 C24 C25 110.22(13) . . ?
C6 C11 H11 119.8 . . ?
C10 C11 C6 120.37(14) . . ?
C10 C11 H11 119.8 . . ?
N4 C12 H12A 109.1 . . ?
N4 C12 H12B 109.1 . . ?
N4 C12 C13 112.39(11) . . ?
H12A C12 H12B 107.9 . . ?
C13 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 120.09(14) . . ?
C9 C8 H8 120.0 . . ?
N3 C19 C20 104.73(11) . . ?
N3 C19 C21 110.39(12) . . ?
N3 C19 C22 109.79(12) . . ?
C20 C19 C22 110.51(12) . . ?
C21 C19 C20 110.19(13) . . ?
C21 C19 C22 111.04(13) . . ?
C12 C13 H13 108.2 . . ?
C12 C13 C14 109.61(12) . . ?
C14 C13 H13 108.2 . . ?
C18 C13 C12 112.01(13) . . ?
C18 C13 H13 108.2 . . ?
C18 C13 C14 110.55(13) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.84(14) . . ?
C10 C9 H9 120.1 . . ?
C11 C10 H10 119.8 . . ?
C9 C10 C11 120.35(14) . . ?
C9 C10 H10 119.8 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C13 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
C13 C14 C15 111.36(13) . . ?
H14A C14 H14B 108.0 . . ?
C15 C14 H14A 109.4 . . ?
C15 C14 H14B 109.4 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C13 C18 H18A 109.4 . . ?
C13 C18 H18B 109.4 . . ?
C13 C18 C17 111.21(15) . . ?
H18A C18 H18B 108.0 . . ?
C17 C18 H18A 109.4 . . ?
C17 C18 H18B 109.4 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C14 C15 H15A 109.3 . . ?
C14 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
C16 C15 C14 111.63(15) . . ?
C16 C15 H15A 109.3 . . ?
C16 C15 H15B 109.3 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 C17 110.65(15) . . ?
H16A C16 H16B 108.1 . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
C18 C17 H17A 109.6 . . ?
C18 C17 H17B 109.6 . . ?
C16 C17 C18 110.47(14) . . ?
C16 C17 H17A 109.6 . . ?
C16 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C3 C4 N4 157.17(12) . . . . ?
O2 C3 C4 C5 -16.3(2) . . . . ?
O2 C2 C1 N2 0.04(15) . . . . ?
O2 C2 C1 C23 -177.77(12) . . . . ?
N2 C3 C4 N4 -18.0(2) . . . . ?
N2 C3 C4 C5 168.48(15) . . . . ?
N2 C1 C23 O1 -173.75(12) . . . . ?
N2 C1 C23 N1 5.1(2) . . . . ?
N4 C4 C5 N6 -0.73(15) . . . . ?
N4 C4 C5 C6 175.84(14) . . . . ?
N4 C12 C13 C14 -168.96(12) . . . . ?
N4 C12 C13 C18 67.95(15) . . . . ?
N5 N4 C4 C3 -174.63(12) . . . . ?
N5 N4 C4 C5 0.57(15) . . . . ?
N5 N4 C12 C13 -93.72(15) . . . . ?
N5 N6 C5 C4 0.65(16) . . . . ?
N5 N6 C5 C6 -176.44(12) . . . . ?
N3 C2 C1 N2 -176.56(14) . . . . ?
N3 C2 C1 C23 5.6(2) . . . . ?
C3 O2 C2 N3 176.64(12) . . . . ?
C3 O2 C2 C1 -0.33(14) . . . . ?
C3 N2 C1 C2 0.30(15) . . . . ?
C3 N2 C1 C23 178.10(13) . . . . ?
C3 C4 C5 N6 173.55(14) . . . . ?
C3 C4 C5 C6 -9.9(3) . . . . ?
C4 N4 N5 N6 -0.18(15) . . . . ?
C4 N4 C12 C13 80.75(17) . . . . ?
C6 C7 C8 C9 -0.5(2) . . . . ?
C6 C11 C10 C9 0.0(2) . . . . ?
C2 O2 C3 N2 0.56(14) . . . . ?
C2 O2 C3 C4 -175.32(11) . . . . ?
C2 N3 C19 C20 175.22(14) . . . . ?
C2 N3 C19 C21 -66.19(19) . . . . ?
C2 N3 C19 C22 56.55(19) . . . . ?
C2 C1 C23 O1 3.7(2) . . . . ?
C2 C1 C23 N1 -177.48(13) . . . . ?
C1 N2 C3 O2 -0.53(15) . . . . ?
C1 N2 C3 C4 174.78(13) . . . . ?
C23 N1 C24 C26 57.21(19) . . . . ?
C23 N1 C24 C25 -65.01(18) . . . . ?
C23 N1 C24 C27 175.68(13) . . . . ?
C5 N6 N5 N4 -0.30(15) . . . . ?
C5 C6 C7 C8 175.98(12) . . . . ?
C5 C6 C11 C10 -175.63(13) . . . . ?
C7 C6 C5 N6 -32.31(19) . . . . ?
C7 C6 C5 C4 151.44(15) . . . . ?
C7 C6 C11 C10 -0.2(2) . . . . ?
C7 C8 C9 C10 0.3(2) . . . . ?
C24 N1 C23 O1 -1.1(2) . . . . ?
C24 N1 C23 C1 -179.83(12) . . . . ?
C11 C6 C5 N6 143.07(14) . . . . ?
C11 C6 C5 C4 -33.2(2) . . . . ?
C11 C6 C7 C8 0.5(2) . . . . ?
C12 N4 N5 N6 175.31(12) . . . . ?
C12 N4 C4 C3 10.5(2) . . . . ?
C12 N4 C4 C5 -174.29(13) . . . . ?
C12 C13 C14 C15 -178.73(14) . . . . ?
C12 C13 C18 C17 178.59(13) . . . . ?
C8 C9 C10 C11 -0.1(2) . . . . ?
C19 N3 C2 O2 25.3(2) . . . . ?
C19 N3 C2 C1 -158.47(15) . . . . ?
C13 C14 C15 C16 55.35(19) . . . . ?
C13 C18 C17 C16 -57.3(2) . . . . ?
C14 C13 C18 C17 56.03(18) . . . . ?
C14 C15 C16 C17 -56.2(2) . . . . ?
C18 C13 C14 C15 -54.77(18) . . . . ?
C15 C16 C17 C18 56.9(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 1.710
_oxdiff_exptl_absorpt_empirical_full_min 0.473
