# Supplementary Information (SI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_ia723e
_database_code_depnum_ccdc_archive 'CCDC 2331026'
loop_
_audit_author_name
_audit_author_address
'Richard J Staples'
;Dartmouth College
United States of America
;
_audit_update_record             
;
2024-02-05 deposited with the CCDC.	2025-06-05 downloaded from the CCDC.
;
_audit_creation_date             2023-07-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H20 N2 O2 Si'
_chemical_formula_sum            'C15 H20 N2 O2 Si'
_chemical_formula_weight         288.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15H20N2O2Si
_chemical_oxdiff_usercomment     'DS-Si ALK V'
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'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.99957(5)
_cell_length_b                   18.62104(13)
_cell_length_c                   12.07918(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.6114(6)
_cell_angle_gamma                90
_cell_volume                     1574.303(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    21509
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.9730
_cell_measurement_theta_min      4.3300
_shelx_estimated_absorpt_T_max   0.841
_shelx_estimated_absorpt_T_min   0.717
_exptl_absorpt_coefficient_mu    1.343
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.476
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
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    1.217
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             616
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 -1 -5 0.1010
2 -11 -2 0.0790
-1 12 1 0.0466
2 -5 -6 0.0678
3 2 6 0.0926
0 4 7 0.0928
-4 4 2 0.0899
-4 1 -4 0.1084
-2 -2 7 0.1415
2 0 -7 0.0813
2 -10 -1 0.0800
-2 11 -1 0.0428
-3 -9 1 0.1064
-4 -4 0 0.0818
0 10 5 0.0635
0 -12 2 0.1065
0 -12 -1 0.0804
-1 -11 -3 0.0789

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.265
_exptl_crystal_size_mid          0.219
_exptl_crystal_size_min          0.134
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
3.3357 -1.2073 -5.3194 -0.0079 -0.3498 0.9368
1.7847 -10.7195 -1.9677 0.0169 0.5973 0.8018
-1.1069 11.6752 0.7822 -0.0210 -0.7619 -0.6473
1.9254 -5.4021 -6.2128 -0.3285 0.0074 0.9445
2.8236 1.6050 6.0022 0.9964 -0.0261 -0.0811
0.4188 4.2735 7.2918 0.7738 -0.0195 -0.6331
-4.1228 4.3191 1.8050 -0.4212 0.0122 -0.9069
-3.9481 0.6619 -3.7826 -0.9423 0.0252 -0.3338
-1.5208 -2.2028 7.2708 0.4420 0.5775 -0.6863
2.1899 -0.2351 -6.9025 -0.3222 -0.4217 0.8476
2.3161 -10.3469 -0.7822 0.2101 0.5897 0.7798
-1.7007 11.1293 -0.8842 -0.2697 -0.7589 -0.5927
-2.8881 -9.1594 1.1937 -0.3760 0.9074 -0.1877
-4.2290 -4.3849 0.3154 -0.6301 0.5971 -0.4964
0.3966 9.6408 4.6817 0.5580 -0.5309 -0.6378
-0.3167 -11.8298 1.5391 0.0250 0.9631 0.2680
0.4160 -11.8396 -1.4522 -0.1464 0.7867 0.5997
-0.6646 -11.2664 -2.6043 -0.4129 0.7595 0.5027

_exptl_special_details           
;
Data was collected using a Rigaku Synergy S Diffractometer diffractometer equipped 
with an Oxford 800 low-temperature apparatus.  A suitable 
crystal was chosen and mounted on a nylon loop using Paratone oil.  Data  were 
measured based on the Pre-Experiment plugin of CrysAlisPro software.  Cell 
parameters were retrieved using CrysAlisPro software and data reduction was 
performed using the intergration software inside the CrysAlisPro which 
corrects for Lp.  The structure was solved by the direct method using the 
SHELXT program and refined by least squares method on F2, SHELXL,
 incorporated in OLEX2. 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            32803
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.273
_diffrn_reflns_theta_min         4.363
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -62.00  25.00   0.50    0.05    --  -47.10  57.00-120.00  174
  2  ω    -70.00  16.00   0.50    0.05    --  -47.10  77.00   0.00  172
  3  ω    -39.00  28.00   0.50    0.05    --  -47.10  19.00   0.00  134
  4  ω    -70.00  16.00   0.50    0.05    --  -47.10  77.00  90.00  172
  5  ω    -39.00  28.00   0.50    0.05    --  -47.10  19.00 150.00  134
  6  ω     34.00 119.00   0.50    0.05    --   47.10  47.00  99.63  170
  7  ω     34.00 119.00   0.50    0.05    --   47.10  47.00 149.52  170
  8  ω     35.00 119.00   0.50    0.05    --   47.10  43.00  56.31  168
  9  ω     35.00 119.00   0.50    0.05    --   47.10  45.00   6.28  168
 10  ω     35.00 119.00   0.50    0.05    --   47.10  42.00 -64.31  168
 11  ω     35.00 119.00   0.50    0.05    --   47.10  46.00-140.97  168
 12  ω    100.00 178.00   0.50    0.07    --  113.25  15.00 -90.00  156
 13  ω    106.00 178.00   0.50    0.07    --  113.25  61.00-180.00  144
 14  ω    101.00 178.00   0.50    0.07    --  113.25  45.00 -60.00  154
 15  ω    101.00 178.00   0.50    0.07    --  113.25  30.00 -90.00  154
 16  ω    101.00 178.00   0.50    0.07    --  113.25  45.00 -30.00  154
 17  ω    106.00 178.00   0.50    0.07    --  113.25  61.00   0.00  144
 18  ω    101.00 178.00   0.50    0.07    --  113.25  39.00  49.39  154
 19  ω    100.00 178.00   0.50    0.07    --  113.25  15.00 120.00  156
 20  ω    100.00 178.00   0.50    0.07    --  113.25  15.00 150.00  156
 21  ω     97.00 178.00   0.50    0.07    --  113.25 125.00 120.00  162
 22  ω     97.00 178.00   0.50    0.07    --  113.25 125.00 -30.00  162
 23  ω     42.00  69.00   0.50    0.07    --  113.25 -61.00-120.00   54
 24  ω     42.00  94.00   0.50    0.07    --  113.25 -77.00-120.00  104
 25  ω     42.00  94.00   0.50    0.07    --  113.25 -77.00  90.00  104
 26  ω     42.00  69.00   0.50    0.07    --  113.25 -61.00  90.00   54
 27  ω     42.00  69.00   0.50    0.07    --  113.25 -61.00  30.00   54
 28  ω     42.00 104.00   0.50    0.07    --  113.25 -94.00 -60.00  124
 29  ω     44.00 105.00   0.50    0.07    --  113.25-106.00-106.58  122
 30  ω     44.00 108.00   0.50    0.07    --  113.25-125.00-150.00  128
 31  ω     42.00 104.00   0.50    0.07    --  113.25 -94.00-180.00  124
 32  ω     36.00  93.00   0.50    0.05    --   47.10-125.00-150.00  114
 33  ω     42.00 104.00   0.50    0.07    --  113.25 -94.00-150.00  124
 34  ω     42.00 104.00   0.50    0.07    --  113.25 -94.00 -90.00  124
 35  ω     42.00 104.00   0.50    0.07    --  113.25 -94.00-120.00  124
 36  ω     44.00 108.00   0.50    0.07    --  113.25-125.00  30.00  128
 37  ω     43.00 104.00   0.50    0.07    --  113.25-103.00  37.22  122
 38  ω     42.00 104.00   0.50    0.07    --  113.25 -94.00  30.00  124
 39  ω     42.00 104.00   0.50    0.07    --  113.25 -94.00  60.00  124
 40  ω     42.00 104.00   0.50    0.07    --  113.25 -94.00  90.00  124
 41  ω     42.00 104.00   0.50    0.07    --  113.25 -94.00 120.00  124
 42  ω     42.00 104.00   0.50    0.07    --  113.25 -94.00 150.00  124
 43  ω    -70.00 -19.00   0.50    0.07    --  -91.75  61.00-180.00  102
 44  ω    -53.00 -20.00   0.50    0.07    --  -91.75  45.00 -30.00   66
 45  ω    -53.00 -20.00   0.50    0.07    --  -91.75  45.00  90.00   66
 46  ω   -163.00-106.00   0.50    0.07    --  -91.75 -61.00  90.00  114
 47  ω   -163.00-106.00   0.50    0.07    --  -91.75 -61.00-150.00  114
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1496819000
_diffrn_orient_matrix_UB_12      0.0061005000
_diffrn_orient_matrix_UB_13      0.0939540000
_diffrn_orient_matrix_UB_21      -0.0611548000
_diffrn_orient_matrix_UB_22      -0.0740223000
_diffrn_orient_matrix_UB_23      0.0442134000
_diffrn_orient_matrix_UB_31      0.1494836000
_diffrn_orient_matrix_UB_32      -0.0363041000
_diffrn_orient_matrix_UB_33      -0.0741291000
_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_current           1
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3295
_reflns_number_total             3414
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         3414
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0329
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0490P)²+0.5634P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0881
_refine_special_details          
;
The structure was refined by Least Squares SHELXL incorporated 
in Olex2 software program. All non-hydrogen atoms were refined anisotropically. 
Hydrogen atom positions were calculated geometrically and refined using the 
riding model, except for the hydrogen atom on the non-carbon atom(s) which were found 
by difference Fourier methods and refined isotropically when data permits.
;
_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 Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C9(H9A,H9B,H9C)
;
_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
Si1 Si 0.63341(4) 0.23601(2) 0.69820(2) 0.01770(10) Uani 1 1 d . . . . .
O1 O 0.78179(11) 0.55884(4) 0.93130(6) 0.02043(18) Uani 1 1 d . . . . .
O2 O 0.70283(12) 0.45210(4) 1.00699(6) 0.02324(18) Uani 1 1 d . . . . .
N1 N 0.73813(14) 0.47792(5) 0.62830(7) 0.01866(19) Uani 1 1 d . . . . .
H1 H 0.715(2) 0.4331(9) 0.6211(12) 0.027(4) Uiso 1 1 d . . . . .
N2 N 0.75038(13) 0.50553(5) 0.72898(7) 0.01795(19) Uani 1 1 d . . . . .
C1 C 0.72724(15) 0.46125(6) 0.81218(9) 0.0180(2) Uani 1 1 d . . . . .
C2 C 0.69421(15) 0.38624(6) 0.79430(9) 0.0191(2) Uani 1 1 d . . . . .
C3 C 0.67129(16) 0.32609(6) 0.75942(9) 0.0204(2) Uani 1 1 d . . . . .
C4 C 0.40165(18) 0.20141(7) 0.74928(10) 0.0275(3) Uani 1 1 d . . . . .
H4A H 0.406668 0.197737 0.830190 0.041 Uiso 1 1 calc R U . . .
H4B H 0.377030 0.153867 0.717383 0.041 Uiso 1 1 calc R U . . .
H4C H 0.298934 0.234363 0.727211 0.041 Uiso 1 1 calc R U . . .
C5 C 0.62689(18) 0.25020(7) 0.54579(10) 0.0260(2) Uani 1 1 d . . . . .
H5A H 0.520903 0.282384 0.526449 0.039 Uiso 1 1 calc R U . . .
H5B H 0.608742 0.203961 0.508372 0.039 Uiso 1 1 calc R U . . .
H5C H 0.747576 0.271724 0.522231 0.039 Uiso 1 1 calc R U . . .
C6 C 0.83429(19) 0.17707(7) 0.74192(10) 0.0291(3) Uani 1 1 d . . . . .
H6A H 0.955423 0.198604 0.719133 0.044 Uiso 1 1 calc R U . . .
H6B H 0.819670 0.129833 0.707083 0.044 Uiso 1 1 calc R U . . .
H6C H 0.833839 0.171663 0.822614 0.044 Uiso 1 1 calc R U . . .
C7 C 0.73448(15) 0.48941(6) 0.92705(9) 0.0181(2) Uani 1 1 d . . . . .
C8 C 0.79099(17) 0.58987(6) 1.04153(9) 0.0207(2) Uani 1 1 d . . . . .
H8A H 0.870962 0.559745 1.091148 0.025 Uiso 1 1 calc R U . . .
H8B H 0.661436 0.593493 1.073139 0.025 Uiso 1 1 calc R U . . .
C9 C 0.87791(18) 0.66341(6) 1.02911(10) 0.0248(2) Uani 1 1 d . . . . .
H9A H 0.798894 0.692188 0.978443 0.037 Uiso 1 1 calc R U . . .
H9B H 1.006974 0.658889 0.999234 0.037 Uiso 1 1 calc R U . . .
H9C H 0.884404 0.686996 1.101584 0.037 Uiso 1 1 calc R U . . .
C10 C 0.76349(15) 0.52021(6) 0.53364(9) 0.0175(2) Uani 1 1 d . . . . .
C11 C 0.82805(16) 0.59078(6) 0.54101(9) 0.0198(2) Uani 1 1 d . . . . .
H11 H 0.855128 0.611940 0.611002 0.024 Uiso 1 1 calc R U . . .
C12 C 0.85214(17) 0.62974(6) 0.44376(10) 0.0242(2) Uani 1 1 d . . . . .
H12 H 0.895481 0.678022 0.447737 0.029 Uiso 1 1 calc R U . . .
C13 C 0.81383(18) 0.59915(7) 0.34108(10) 0.0256(2) Uani 1 1 d . . . . .
H13 H 0.831065 0.626350 0.275400 0.031 Uiso 1 1 calc R U . . .
C14 C 0.75025(17) 0.52865(6) 0.33481(9) 0.0234(2) Uani 1 1 d . . . . .
H14 H 0.724362 0.507447 0.264706 0.028 Uiso 1 1 calc R U . . .
C15 C 0.72445(16) 0.48908(6) 0.43095(9) 0.0206(2) Uani 1 1 d . . . . .
H15 H 0.680300 0.440902 0.426728 0.025 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
Si1 C3 1.8511(12) . ?
Si1 C4 1.8571(12) . ?
Si1 C5 1.8600(12) . ?
Si1 C6 1.8558(12) . ?
O1 C7 1.3355(13) . ?
O1 C8 1.4521(12) . ?
O2 C7 1.2118(13) . ?
N1 H1 0.854(16) . ?
N1 N2 1.3223(12) . ?
N1 C10 1.4012(13) . ?
N2 C1 1.3113(14) . ?
C1 C2 1.4317(15) . ?
C1 C7 1.4836(15) . ?
C2 C3 1.2069(16) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.5067(15) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.3922(15) . ?
C10 C15 1.3936(15) . ?
C11 H11 0.9500 . ?
C11 C12 1.3924(16) . ?
C12 H12 0.9500 . ?
C12 C13 1.3884(17) . ?
C13 H13 0.9500 . ?
C13 C14 1.3880(17) . ?
C14 H14 0.9500 . ?
C14 C15 1.3888(16) . ?
C15 H15 0.9500 . ?

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 Si1 C4 107.67(5) . . ?
C3 Si1 C5 105.58(5) . . ?
C3 Si1 C6 108.50(6) . . ?
C4 Si1 C5 111.46(6) . . ?
C6 Si1 C4 111.24(6) . . ?
C6 Si1 C5 112.10(6) . . ?
C7 O1 C8 115.40(8) . . ?
N2 N1 H1 118.9(10) . . ?
N2 N1 C10 121.64(9) . . ?
C10 N1 H1 119.4(10) . . ?
C1 N2 N1 116.94(9) . . ?
N2 C1 C2 121.25(10) . . ?
N2 C1 C7 119.42(9) . . ?
C2 C1 C7 119.32(9) . . ?
C3 C2 C1 168.17(11) . . ?
C2 C3 Si1 176.80(10) . . ?
Si1 C4 H4A 109.5 . . ?
Si1 C4 H4B 109.5 . . ?
Si1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
Si1 C5 H5A 109.5 . . ?
Si1 C5 H5B 109.5 . . ?
Si1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
Si1 C6 H6A 109.5 . . ?
Si1 C6 H6B 109.5 . . ?
Si1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O1 C7 C1 112.59(9) . . ?
O2 C7 O1 124.87(10) . . ?
O2 C7 C1 122.54(10) . . ?
O1 C8 H8A 110.4 . . ?
O1 C8 H8B 110.4 . . ?
O1 C8 C9 106.52(9) . . ?
H8A C8 H8B 108.6 . . ?
C9 C8 H8A 110.4 . . ?
C9 C8 H8B 110.4 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 N1 121.48(10) . . ?
C11 C10 C15 120.67(10) . . ?
C15 C10 N1 117.85(10) . . ?
C10 C11 H11 120.7 . . ?
C10 C11 C12 118.68(10) . . ?
C12 C11 H11 120.7 . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 121.07(11) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.70(11) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.05(11) . . ?
C15 C14 H14 120.0 . . ?
C10 C15 H15 120.1 . . ?
C14 C15 C10 119.84(10) . . ?
C14 C15 H15 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N2 C1 C2 1.25(15) . . . . ?
N1 N2 C1 C7 -178.45(9) . . . . ?
N1 C10 C11 C12 179.35(10) . . . . ?
N1 C10 C15 C14 -179.06(10) . . . . ?
N2 N1 C10 C11 8.85(15) . . . . ?
N2 N1 C10 C15 -172.02(10) . . . . ?
N2 C1 C2 C3 4.5(6) . . . . ?
N2 C1 C7 O1 -5.47(14) . . . . ?
N2 C1 C7 O2 175.46(10) . . . . ?
C2 C1 C7 O1 174.82(9) . . . . ?
C2 C1 C7 O2 -4.25(16) . . . . ?
C7 O1 C8 C9 170.59(9) . . . . ?
C7 C1 C2 C3 -175.8(5) . . . . ?
C8 O1 C7 O2 -1.10(15) . . . . ?
C8 O1 C7 C1 179.85(9) . . . . ?
C10 N1 N2 C1 -178.99(9) . . . . ?
C10 C11 C12 C13 -0.32(17) . . . . ?
C11 C10 C15 C14 0.08(16) . . . . ?
C11 C12 C13 C14 0.08(18) . . . . ?
C12 C13 C14 C15 0.25(18) . . . . ?
C13 C14 C15 C10 -0.33(17) . . . . ?
C15 C10 C11 C12 0.25(16) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id 'DS-Si ALK V'
_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 1.587
_oxdiff_exptl_absorpt_empirical_full_min 0.674
####################################################################### 
# 
# 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_ia723b
_database_code_depnum_ccdc_archive 'CCDC 2331030'
loop_
_audit_author_name
_audit_author_address
'Richard J Staples'
;Dartmouth College
United States of America
;
_audit_update_record             
;
2024-02-05 deposited with the CCDC.	2025-06-05 downloaded from the CCDC.
;
_audit_creation_date             2023-07-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H16 N2 O2'
_chemical_formula_sum            'C18 H16 N2 O2'
_chemical_formula_weight         292.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         C18H16N2O2
_chemical_oxdiff_usercomment     'DS-ben alk V'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   13.24004(11)
_cell_length_b                   11.03585(11)
_cell_length_c                   20.65862(17)
_cell_angle_alpha                90
_cell_angle_beta                 91.2541(7)
_cell_angle_gamma                90
_cell_volume                     3017.81(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9995
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      79.2140
_cell_measurement_theta_min      4.2770
_shelx_estimated_absorpt_T_max   0.931
_shelx_estimated_absorpt_T_min   0.875
_exptl_absorpt_coefficient_mu    0.685
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89533
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
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    1.287
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1232
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.1174
0 -1 0 0.0798
-3 1 13 0.0729
3 -1 -13 0.0612
-9 0 0 0.0906
9 0 0 0.0726
0 0 13 0.0532
0 0 -13 0.0519
6 5 -2 0.1236
-6 -5 0 0.1035
1 4 11 0.0870
4 -6 -3 0.0849
0 6 -8 0.1146
7 -4 -4 0.0642
7 -5 1 0.0642
6 -1 -9 0.0657
0 2 -13 0.0684
0 -2 13 0.0668

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.106
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0007 1.0006 0.0012 -0.0587 -0.1208 -0.0384
-0.0007 -1.0006 -0.0012 0.0587 0.1208 0.0384
-2.9488 0.9135 12.5836 -0.1692 -0.3578 0.9188
2.9619 -0.5515 -12.6509 0.1489 0.3153 -0.9378
-8.5920 0.0027 0.1438 0.8087 -0.4946 0.3187
8.5922 0.0025 -0.1756 -0.8080 0.4941 -0.3210
-0.1727 0.2731 13.3959 -0.4200 -0.1262 0.8983
0.2227 -0.2318 -13.3987 0.4130 0.1241 -0.9019
6.1006 4.9821 -1.6561 -0.8171 -0.2409 -0.5226
-6.1060 -5.0342 0.1454 0.8681 0.2563 0.4230
1.3569 4.1350 10.6798 -0.7056 -0.4877 0.5118
3.5265 -6.3514 -2.8771 0.1282 0.9872 -0.0766
-0.1729 5.8787 -7.6306 -0.0882 -0.6722 -0.7339
7.1569 -3.5224 -3.6155 -0.3579 0.8587 -0.3657
6.6455 -4.5036 0.5835 -0.3839 0.9217 -0.0267
6.2846 -1.2490 -9.0692 -0.2372 0.5680 -0.7892
-0.2174 2.0663 -12.8242 0.3021 -0.1822 -0.9357
-0.3757 -2.0829 12.8237 -0.2450 0.1502 0.9576

_exptl_special_details           
;
Data was collected using a Rigaku Synergy S Diffractometer diffractometer equipped 
with an Oxford 800 low-temperature apparatus.  A suitable 
crystal was chosen and mounted on a nylon loop using Paratone oil.  Data  were 
measured based on the Pre-Experiment plugin of CrysAlisPro software.  Cell 
parameters were retrieved using CrysAlisPro software and data reduction was 
performed using the intergration software inside the CrysAlisPro which 
corrects for Lp.  The structure was solved by the direct method using the 
SHELXT program and refined by least squares method on F2, SHELXL,
 incorporated in OLEX2. 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16466
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.299
_diffrn_reflns_theta_min         4.281
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -78.00   5.00   0.50    0.06    --  -47.10 103.00 -64.00  166
  2  ω     17.00  82.00   0.50    0.06    --   47.10-103.00-166.00  130
  3  ω   -162.00 -86.00   0.50    0.23    --  -91.75-103.00-166.00  152
  4  ω    -78.00 -21.00   0.50    0.23    --  -91.75 103.00 -64.00  114
  5  ω     43.00 104.00   0.50    0.23    --  113.25-103.00-166.00  122
  6  ω    108.00 178.00   0.50    0.23    --  113.25 103.00 -64.00  140
  7  ω    -47.00  26.00   0.50    0.06    --  -47.10  37.00-180.00  146
  8  ω    -83.00 -15.00   0.50    0.06    --  -47.10 125.00  90.00  136
  9  ω    -47.00  26.00   0.50    0.06    --  -47.10  37.00  60.00  146
 10  ω    -53.00 -20.00   0.50    0.23    --  -91.75  45.00-120.00   66
 11  ω    -53.00 -20.00   0.50    0.23    --  -91.75  45.00 150.00   66
 12  ω    -53.00 -20.00   0.50    0.23    --  -91.75  45.00 120.00   66
 13  ω    -53.00 -20.00   0.50    0.23    --  -91.75  45.00-150.00   66
 14  ω     42.00  69.00   0.50    0.23    --  113.25 -61.00-150.00   54
 15  ω    100.00 178.00   0.50    0.23    --  113.25  15.00 -60.00  156
 16  ω     42.00  69.00   0.50    0.23    --  113.25 -61.00  90.00   54
 17  ω     42.00  69.00   0.50    0.23    --  113.25 -61.00 -60.00   54
 18  ω    110.00 178.00   0.50    0.23    --  113.25  77.00 -90.00  136
 19  ω     42.00  94.00   0.50    0.23    --  113.25 -77.00  30.00  104
 20  ω     42.00  69.00   0.50    0.23    --  113.25 -61.00  30.00   54
 21  ω     42.00 104.00   0.50    0.23    --  113.25 -94.00-120.00  124
 22  ω    106.00 178.00   0.50    0.23    --  113.25  61.00-180.00  144
 23  ω     43.00  68.00   0.50    0.23    --  113.25 -61.00  60.00   50
 24  ω     42.00  67.00   0.50    0.23    --  113.25 -61.00   0.00   50
 25  ω     72.00  98.00   0.50    0.23    --  113.25 -94.00-150.00   52
 26  ω     46.00  89.00   0.50    0.23    --  113.25 -77.00  60.00   86
 27  ω     58.00  84.00   0.50    0.23    --  113.25 -77.00 -30.00   52
 28  ω     51.00 101.00   0.50    0.23    --  113.25 -94.00 -90.00  100
 29  ω     42.00  67.00   0.50    0.23    --  113.25 -61.00-180.00   50
 30  ω     43.00  69.00   0.50    0.23    --  113.25 -61.00-120.00   52
 31  ω    110.00 166.00   0.50    0.23    --  113.25  61.00 120.00  112
 32  ω    123.00 171.00   0.50    0.23    --  113.25 125.00  90.00   96
 33  ω     42.00  94.00   0.50    0.23    --  113.25 -77.00-180.00  104
 34  ω     42.00  67.00   0.50    0.23    --  113.25 -61.00 -30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0946654000
_diffrn_orient_matrix_UB_12      -0.0585234000
_diffrn_orient_matrix_UB_13      -0.0313819000
_diffrn_orient_matrix_UB_21      0.0574186000
_diffrn_orient_matrix_UB_22      -0.1207265000
_diffrn_orient_matrix_UB_23      -0.0062168000
_diffrn_orient_matrix_UB_31      -0.0359758000
_diffrn_orient_matrix_UB_32      -0.0384378000
_diffrn_orient_matrix_UB_33      0.0673792000
_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_current           1
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2959
_reflns_number_total             3244
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.00034(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0359
_refine_ls_restrained_S_all      1.076
_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)+(0.0491P)²+1.6145P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1010
_refine_special_details          
;
The structure was refined by Least Squares SHELXL incorporated 
in Olex2 software program. All non-hydrogen atoms were refined anisotropically. 
Hydrogen atom positions were calculated geometrically and refined using the 
riding model, except for the hydrogen atom on the non-carbon atom(s) which were found 
by difference Fourier methods and refined isotropically when data permits.
;
_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 Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.62408(6) 0.99608(7) 0.59704(4) 0.02558(19) Uani 1 1 d . . . . .
O2 O 0.62470(7) 0.98527(8) 0.48790(4) 0.0333(2) Uani 1 1 d . . . . .
N1 N 0.62543(7) 0.61544(8) 0.51234(4) 0.0239(2) Uani 1 1 d . . . . .
H1 H 0.6194(12) 0.5904(16) 0.5546(8) 0.042(4) Uiso 1 1 d . . . . .
N2 N 0.62634(7) 0.73358(8) 0.50136(4) 0.0233(2) Uani 1 1 d . . . . .
C1 C 0.62270(8) 0.80448(10) 0.55230(5) 0.0228(2) Uani 1 1 d . . . . .
C2 C 0.62395(8) 0.93761(10) 0.54028(5) 0.0239(2) Uani 1 1 d . . . . .
C3 C 0.61832(8) 0.75653(10) 0.61640(5) 0.0229(2) Uani 1 1 d . . . . .
C4 C 0.61486(8) 0.69655(10) 0.66451(5) 0.0234(2) Uani 1 1 d . . . . .
C5 C 0.60998(8) 0.62506(10) 0.72227(5) 0.0219(2) Uani 1 1 d . . . . .
C6 C 0.64218(8) 0.67208(10) 0.78221(5) 0.0247(2) Uani 1 1 d . . . . .
H6 H 0.667593 0.752461 0.784922 0.030 Uiso 1 1 calc R U . . .
C7 C 0.63707(8) 0.60175(11) 0.83750(5) 0.0264(2) Uani 1 1 d . . . . .
H7 H 0.659623 0.633624 0.878016 0.032 Uiso 1 1 calc R U . . .
C8 C 0.59895(9) 0.48442(10) 0.83382(5) 0.0260(2) Uani 1 1 d . . . . .
H8 H 0.594866 0.436662 0.871930 0.031 Uiso 1 1 calc R U . . .
C9 C 0.56689(9) 0.43692(10) 0.77468(5) 0.0266(2) Uani 1 1 d . . . . .
H9 H 0.540951 0.356741 0.772384 0.032 Uiso 1 1 calc R U . . .
C10 C 0.57265(8) 0.50635(10) 0.71890(5) 0.0248(2) Uani 1 1 d . . . . .
H10 H 0.551278 0.473394 0.678389 0.030 Uiso 1 1 calc R U . . .
C11 C 0.62395(10) 1.12730(10) 0.59402(6) 0.0296(3) Uani 1 1 d . . . . .
H11A H 0.560374 1.156987 0.573494 0.035 Uiso 1 1 calc R U . . .
H11B H 0.681420 1.156615 0.568451 0.035 Uiso 1 1 calc R U . . .
C12 C 0.63338(10) 1.17156(11) 0.66294(6) 0.0328(3) Uani 1 1 d . . . . .
H12A H 0.635871 1.260306 0.663322 0.049 Uiso 1 1 calc R U . . .
H12B H 0.695438 1.139171 0.683045 0.049 Uiso 1 1 calc R U . . .
H12C H 0.574956 1.143956 0.687254 0.049 Uiso 1 1 calc R U . . .
C13 C 0.63319(8) 0.52964(10) 0.46287(5) 0.0224(2) Uani 1 1 d . . . . .
C14 C 0.62299(8) 0.40797(10) 0.47958(5) 0.0261(2) Uani 1 1 d . . . . .
H14 H 0.609756 0.386102 0.523054 0.031 Uiso 1 1 calc R U . . .
C15 C 0.63214(9) 0.31882(11) 0.43278(6) 0.0301(3) Uani 1 1 d . . . . .
H15 H 0.625228 0.235890 0.444183 0.036 Uiso 1 1 calc R U . . .
C16 C 0.65140(9) 0.35082(12) 0.36929(6) 0.0321(3) Uani 1 1 d . . . . .
H16 H 0.657342 0.289947 0.337078 0.039 Uiso 1 1 calc R U . . .
C17 C 0.66197(9) 0.47234(12) 0.35298(6) 0.0321(3) Uani 1 1 d . . . . .
H17 H 0.675623 0.494014 0.309532 0.038 Uiso 1 1 calc R U . . .
C18 C 0.65282(9) 0.56224(11) 0.39935(5) 0.0279(2) Uani 1 1 d . . . . .
H18 H 0.659867 0.645123 0.387875 0.034 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.3384(13) . ?
O1 C11 1.4495(13) . ?
O2 C2 1.2034(13) . ?
N1 H1 0.921(17) . ?
N1 N2 1.3234(13) . ?
N1 C13 1.3985(13) . ?
N2 C1 1.3131(14) . ?
C1 C2 1.4902(15) . ?
C1 C3 1.4283(14) . ?
C3 C4 1.1960(15) . ?
C4 C5 1.4330(14) . ?
C5 C6 1.4005(15) . ?
C5 C10 1.4013(15) . ?
C6 H6 0.9500 . ?
C6 C7 1.3838(15) . ?
C7 H7 0.9500 . ?
C7 C8 1.3911(16) . ?
C8 H8 0.9500 . ?
C8 C9 1.3873(16) . ?
C9 H9 0.9500 . ?
C9 C10 1.3873(15) . ?
C10 H10 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.5079(16) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.3937(16) . ?
C13 C18 1.3906(15) . ?
C14 H14 0.9500 . ?
C14 C15 1.3865(16) . ?
C15 H15 0.9500 . ?
C15 C16 1.3874(18) . ?
C16 H16 0.9500 . ?
C16 C17 1.3906(19) . ?
C17 H17 0.9500 . ?
C17 C18 1.3864(16) . ?
C18 H18 0.9500 . ?

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 O1 C11 116.36(8) . . ?
N2 N1 H1 117.3(11) . . ?
N2 N1 C13 122.73(9) . . ?
C13 N1 H1 119.9(11) . . ?
C1 N2 N1 116.68(9) . . ?
N2 C1 C2 116.95(9) . . ?
N2 C1 C3 121.68(10) . . ?
C3 C1 C2 121.37(9) . . ?
O1 C2 C1 109.22(9) . . ?
O2 C2 O1 125.25(10) . . ?
O2 C2 C1 125.53(10) . . ?
C4 C3 C1 168.14(11) . . ?
C3 C4 C5 179.57(12) . . ?
C6 C5 C4 120.92(10) . . ?
C6 C5 C10 119.37(9) . . ?
C10 C5 C4 119.72(9) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.17(10) . . ?
C7 C6 H6 119.9 . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C8 120.07(10) . . ?
C8 C7 H7 120.0 . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.23(10) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.09(10) . . ?
C10 C9 H9 120.0 . . ?
C5 C10 H10 120.0 . . ?
C9 C10 C5 120.06(10) . . ?
C9 C10 H10 120.0 . . ?
O1 C11 H11A 110.4 . . ?
O1 C11 H11B 110.4 . . ?
O1 C11 C12 106.43(9) . . ?
H11A C11 H11B 108.6 . . ?
C12 C11 H11A 110.4 . . ?
C12 C11 H11B 110.4 . . ?
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 . . ?
C14 C13 N1 117.53(10) . . ?
C18 C13 N1 122.18(10) . . ?
C18 C13 C14 120.27(10) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.04(11) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 119.96(11) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.74(10) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.79(11) . . ?
C18 C17 H17 119.6 . . ?
C13 C18 H18 120.4 . . ?
C17 C18 C13 119.20(11) . . ?
C17 C18 H18 120.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N2 C1 C2 179.86(9) . . . . ?
N1 N2 C1 C3 0.20(15) . . . . ?
N1 C13 C14 C15 -178.63(10) . . . . ?
N1 C13 C18 C17 178.46(10) . . . . ?
N2 N1 C13 C14 -174.82(10) . . . . ?
N2 N1 C13 C18 6.74(16) . . . . ?
N2 C1 C2 O1 -177.46(9) . . . . ?
N2 C1 C2 O2 2.55(17) . . . . ?
N2 C1 C3 C4 -0.7(6) . . . . ?
C2 O1 C11 C12 -175.15(9) . . . . ?
C2 C1 C3 C4 179.7(5) . . . . ?
C3 C1 C2 O1 2.20(14) . . . . ?
C3 C1 C2 O2 -177.79(11) . . . . ?
C4 C5 C6 C7 -179.91(10) . . . . ?
C4 C5 C10 C9 -179.45(10) . . . . ?
C5 C6 C7 C8 -0.65(16) . . . . ?
C6 C5 C10 C9 0.64(16) . . . . ?
C6 C7 C8 C9 0.68(17) . . . . ?
C7 C8 C9 C10 -0.04(17) . . . . ?
C8 C9 C10 C5 -0.62(17) . . . . ?
C10 C5 C6 C7 -0.01(16) . . . . ?
C11 O1 C2 O2 0.74(16) . . . . ?
C11 O1 C2 C1 -179.24(9) . . . . ?
C13 N1 N2 C1 -177.27(9) . . . . ?
C13 C14 C15 C16 -0.04(17) . . . . ?
C14 C13 C18 C17 0.07(16) . . . . ?
C14 C15 C16 C17 0.34(17) . . . . ?
C15 C16 C17 C18 -0.44(18) . . . . ?
C16 C17 C18 C13 0.24(18) . . . . ?
C18 C13 C14 C15 -0.16(16) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id 'DS-ben alk V'
_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 1.125
_oxdiff_exptl_absorpt_empirical_full_min 0.875
####################################################################### 
# 
# 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_ia923d
_database_code_depnum_ccdc_archive 'CCDC 2421980'
loop_
_audit_author_name
_audit_author_address
'Richard Staples'
;Dartmouth College
United States of America
;
_audit_update_record             
;
2025-02-06 deposited with the CCDC.	2025-06-05 downloaded from the CCDC.
;
_audit_creation_date             2023-09-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H21 N3 O2'
_chemical_formula_sum            'C20 H21 N3 O2'
_chemical_formula_weight         335.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H21N3O2
_chemical_oxdiff_usercomment     DS-dma-v
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                   12.27152(18)
_cell_length_b                   12.39856(18)
_cell_length_c                   12.5695(2)
_cell_angle_alpha                90.2480(13)
_cell_angle_beta                 91.2744(13)
_cell_angle_gamma                109.7446(13)
_cell_volume                     1799.42(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    23428
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      79.8870
_cell_measurement_theta_min      3.5160
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.653
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.764
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.99a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
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    1.238
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             712
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.0798
-1 0 0 0.0849
-1 8 1 0.0697
1 -8 -1 0.0883
0 0 8 0.0795
0 0 -8 0.1105
-3 5 -6 0.1164
-4 1 -7 0.1189
0 4 7 0.0836

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.223
_exptl_crystal_size_mid          0.209
_exptl_crystal_size_min          0.165
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.9996 0.0005 0.0017 -0.0230 -0.1215 -0.0501
-0.9994 -0.0012 -0.0020 0.0231 0.1215 0.0500
-1.4160 7.7918 1.4886 -0.0665 -0.5190 0.8515
0.7318 -7.6579 -1.4179 0.0750 0.5907 -0.8027
-0.3352 -0.1014 8.1605 -0.9719 0.1261 0.2012
0.3168 0.1253 -8.1515 0.9715 -0.1259 -0.1978
-3.2477 4.9581 -6.1544 0.8629 -0.1115 0.4908
-3.6448 1.0191 -7.1489 0.9510 0.2838 0.1105
-0.0400 3.5111 7.1762 -0.8237 -0.2458 0.5084

_exptl_special_details           
;
Data was collected using a Rigaku Synergy S Diffractometer diffractometer equipped 
with an Oxford 800 low-temperature apparatus.  A suitable 
crystal was chosen and mounted on a nylon loop using Paratone oil.  Data  were 
measured based on the Pre-Experiment plugin of CrysAlisPro software.  Cell 
parameters were retrieved using CrysAlisPro software and data reduction was 
performed using the intergration software inside the CrysAlisPro which 
corrects for Lp.  The structure was solved by the direct method using the 
SHELXT program and refined by least squares method on F2, SHELXL,
 incorporated in OLEX2. 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            38381
_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         80.313
_diffrn_reflns_theta_min         3.517
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_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    -70.00  16.00   0.50    0.05    --  -47.11  77.00   0.00  172
  2  ω    -47.00  26.00   0.50    0.05    --  -47.11  37.00 -60.00  146
  3  ω    -47.00  26.00   0.50    0.05    --  -47.11  37.00-120.00  146
  4  ω    -53.00 -20.00   0.50    0.11    --  -91.75  45.00-180.00   66
  5  ω   -119.00 -34.00   0.50    0.05    --  -47.11 -43.00 -36.97  170
  6  ω   -160.00 -83.00   0.50    0.11    --  -91.75-112.00 -51.00  154
  7  ω   -163.00 -88.00   0.50    0.11    --  -91.75 -48.00  21.88  150
  8  ω   -163.00-110.00   0.50    0.11    --  -91.75 -77.00 150.00  106
  9  ω    -80.00  -5.00   0.50    0.05    --  -47.11 112.00  42.00  150
 10  ω    -81.00 -23.00   0.50    0.11    --  -91.75 112.00  42.00  116
 11  ω   -118.00 -34.00   0.50    0.05    --  -47.11 -46.00-152.26  168
 12  ω     42.00  69.00   0.50    0.11    --  113.25 -61.00-180.00   54
 13  ω     42.00  94.00   0.50    0.11    --  113.25 -77.00-120.00  104
 14  ω     42.00  94.00   0.50    0.11    --  113.25 -77.00  60.00  104
 15  ω     42.00  69.00   0.50    0.11    --  113.25 -61.00 150.00   54
 16  ω    105.00 178.00   0.50    0.11    --  113.25 112.00  42.00  146
 17  ω     97.00 178.00   0.50    0.11    --  113.25 125.00-120.00  162
 18  ω     42.00  69.00   0.50    0.11    --  113.25 -61.00-150.00   54
 19  ω     36.00  93.00   0.50    0.05    --   47.11-125.00  30.00  114
 20  ω     44.00 108.00   0.50    0.11    --  113.25-125.00 -90.00  128
 21  ω     44.00 108.00   0.50    0.11    --  113.25-125.00 -60.00  128
 22  ω     44.00 108.00   0.50    0.11    --  113.25-125.00 -30.00  128
 23  ω     44.00 108.00   0.50    0.11    --  113.25-125.00-150.00  128
 24  ω     27.00  85.00   0.50    0.05    --   47.11-112.00 -51.00  116
 25  ω     45.00 106.00   0.50    0.11    --  113.25-112.00 -51.00  122
 26  ω     43.00 105.00   0.50    0.11    --  113.25-104.00-133.08  124
 27  ω     42.00 104.00   0.50    0.11    --  113.25 -94.00   0.00  124
 28  ω     44.00 108.00   0.50    0.11    --  113.25-125.00  30.00  128
 29  ω     44.00 108.00   0.50    0.11    --  113.25-125.00  90.00  128
 30  ω     44.00 108.00   0.50    0.11    --  113.25-125.00 150.00  128
 31  ω     42.00 104.00   0.50    0.11    --  113.25 -94.00 150.00  124
 32  ω     42.00 104.00   0.50    0.11    --  113.25 -94.00 120.00  124
 33  ω     42.00 104.00   0.50    0.11    --  113.25 -94.00  90.00  124
 34  ω     42.00 104.00   0.50    0.11    --  113.25 -94.00  60.00  124
 35  ω     42.00 104.00   0.50    0.11    --  113.25 -94.00  30.00  124
 36  ω     42.00 104.00   0.50    0.11    --  113.25 -94.00 -30.00  124
 37  ω     42.00 104.00   0.50    0.11    --  113.25 -94.00 -60.00  124
 38  ω    100.00 178.00   0.50    0.11    --  113.25  15.00 120.00  156
 39  ω    106.00 178.00   0.50    0.11    --  113.25  61.00 150.00  144
 40  ω    106.00 178.00   0.50    0.11    --  113.25  61.00  30.00  144
 41  ω    101.00 178.00   0.50    0.11    --  113.25  45.00 -30.00  154
 42  ω    101.00 178.00   0.50    0.11    --  113.25  45.00 -90.00  154
 43  ω    101.00 178.00   0.50    0.11    --  113.25  45.00-150.00  154
 44  ω    101.00 178.00   0.50    0.11    --  113.25  30.00-150.00  154
 45  ω    106.00 178.00   0.50    0.11    --  113.25  61.00 -60.00  144
 46  ω    100.00 178.00   0.50    0.11    --  113.25  15.00  30.00  156
 47  ω     34.00 119.00   0.50    0.05    --   47.11  47.00  77.36  170
 48  ω     34.00  79.00   0.50    0.05    --   47.11  47.00 155.66   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0228572000
_diffrn_orient_matrix_UB_12      0.0102199000
_diffrn_orient_matrix_UB_13      -0.1199113000
_diffrn_orient_matrix_UB_21      -0.1214785000
_diffrn_orient_matrix_UB_22      -0.0904671000
_diffrn_orient_matrix_UB_23      0.0093384000
_diffrn_orient_matrix_UB_31      -0.0502237000
_diffrn_orient_matrix_UB_32      0.0956133000
_diffrn_orient_matrix_UB_33      0.0237832000
_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_current           1
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6997
_reflns_number_total             7712
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     465
_refine_ls_number_reflns         7712
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0383
_refine_ls_restrained_S_all      1.075
_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)+(0.0575P)²+0.3485P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1076
_refine_special_details          
;
The structure was refined by Least Squares SHELXL incorporated 
in Olex2 software program. All non-hydrogen atoms were refined anisotropically. 
Hydrogen atom positions were calculated geometrically and refined using the 
riding model, except for the hydrogen atom on the non-carbon atom(s) which were found 
by difference Fourier methods and refined isotropically when data permits.
;
_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 Secondary CH2 refined with riding coordinates:
 C13A(H13A,H13B), C13B(H13C,H13D)
2.b Aromatic/amide H refined with riding coordinates:
 C5A(H5A), C6A(H6A), C8A(H8A), C9A(H9A), C16A(H16A), C17A(H17A), C18A(H18A),
 C19A(H19A), C20A(H20A), C5B(H5B), C6B(H6B), C8B(H8B), C9B(H9B), C16B(H16B),
 C17B(H17B), C18B(H18B), C19B(H19B), C20B(H20B)
2.c Idealised Me refined as rotating group:
 C10A(H10A,H10B,H10C), C11A(H11A,H11B,H11C), C14A(H14A,H14B,H14C), C10B(H10D,
 H10E,H10F), C11B(H11D,H11E,H11F), C14B(H14D,H14E,H14F)
;
_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
O1A O 0.78257(7) 0.83587(7) 0.72860(6) 0.02986(17) Uani 1 1 d . . . . .
O2A O 0.59326(7) 0.76277(8) 0.68328(6) 0.03234(18) Uani 1 1 d . . . . .
N1A N 0.71472(8) 0.77395(8) 1.03334(7) 0.02323(18) Uani 1 1 d . . . . .
N2A N 0.73617(7) 0.79838(7) 0.93173(7) 0.02254(17) Uani 1 1 d . . . . .
N3A N 0.00971(8) 0.33027(9) 1.04842(8) 0.0327(2) Uani 1 1 d . . . . .
C1A C 0.64866(9) 0.76094(8) 0.86391(8) 0.0224(2) Uani 1 1 d . . . . .
C2A C 0.53392(9) 0.69551(9) 0.89273(8) 0.0244(2) Uani 1 1 d . . . . .
C3A C 0.44034(9) 0.63692(9) 0.92350(8) 0.0249(2) Uani 1 1 d . . . . .
C4A C 0.32987(9) 0.56380(9) 0.95705(8) 0.0241(2) Uani 1 1 d . . . . .
C5A C 0.23235(9) 0.53491(9) 0.88814(8) 0.0260(2) Uani 1 1 d . . . . .
H5A H 0.239150 0.568544 0.819754 0.031 Uiso 1 1 calc R U . . .
C6A C 0.12690(9) 0.45873(9) 0.91763(8) 0.0269(2) Uani 1 1 d . . . . .
H6A H 0.062614 0.440323 0.869085 0.032 Uiso 1 1 calc R U . . .
C7A C 0.11310(9) 0.40773(9) 1.01886(8) 0.0251(2) Uani 1 1 d . . . . .
C8A C 0.21074(9) 0.43972(9) 1.08897(8) 0.0252(2) Uani 1 1 d . . . . .
H8A H 0.203646 0.408560 1.158425 0.030 Uiso 1 1 calc R U . . .
C9A C 0.31612(9) 0.51529(9) 1.05854(8) 0.0254(2) Uani 1 1 d . . . . .
H9A H 0.380416 0.534764 1.107134 0.030 Uiso 1 1 calc R U . . .
C10A C -0.08839(10) 0.29460(10) 0.97421(10) 0.0339(2) Uani 1 1 d . . . . .
H10A H -0.109763 0.361225 0.954105 0.051 Uiso 1 1 calc R U . . .
H10B H -0.154105 0.237679 1.007854 0.051 Uiso 1 1 calc R U . . .
H10C H -0.067611 0.260770 0.910513 0.051 Uiso 1 1 calc R U . . .
C11A C 0.00013(11) 0.27554(12) 1.15102(11) 0.0414(3) Uani 1 1 d . . . . .
H11A H 0.057435 0.236640 1.157404 0.062 Uiso 1 1 calc R U . . .
H11B H -0.077832 0.219375 1.157392 0.062 Uiso 1 1 calc R U . . .
H11C H 0.014313 0.333555 1.207675 0.062 Uiso 1 1 calc R U . . .
C12A C 0.67051(9) 0.78687(9) 0.75004(8) 0.0235(2) Uani 1 1 d . . . . .
C13A C 0.80980(10) 0.86347(10) 0.61790(8) 0.0301(2) Uani 1 1 d . . . . .
H13A H 0.811786 0.942457 0.603061 0.036 Uiso 1 1 calc R U . . .
H13B H 0.750337 0.809867 0.570399 0.036 Uiso 1 1 calc R U . . .
C14A C 0.92620(11) 0.85297(11) 0.59934(9) 0.0361(3) Uani 1 1 d . . . . .
H14A H 0.950330 0.877706 0.527054 0.054 Uiso 1 1 calc R U . . .
H14B H 0.921332 0.772959 0.607895 0.054 Uiso 1 1 calc R U . . .
H14C H 0.982947 0.901386 0.650963 0.054 Uiso 1 1 calc R U . . .
C15A C 0.80477(9) 0.80844(8) 1.10977(8) 0.02158(19) Uani 1 1 d . . . . .
C16A C 0.78291(9) 0.76384(9) 1.21172(8) 0.0236(2) Uani 1 1 d . . . . .
H16A H 0.708682 0.711462 1.227890 0.028 Uiso 1 1 calc R U . . .
C17A C 0.87013(10) 0.79639(9) 1.28933(8) 0.0266(2) Uani 1 1 d . . . . .
H17A H 0.855567 0.765767 1.358799 0.032 Uiso 1 1 calc R U . . .
C18A C 0.97872(10) 0.87343(9) 1.26647(9) 0.0284(2) Uani 1 1 d . . . . .
H18A H 1.038333 0.895119 1.319913 0.034 Uiso 1 1 calc R U . . .
C19A C 0.99957(9) 0.91851(9) 1.16508(9) 0.0291(2) Uani 1 1 d . . . . .
H19A H 1.073334 0.972250 1.149632 0.035 Uiso 1 1 calc R U . . .
C20A C 0.91340(9) 0.88566(9) 1.08598(8) 0.0262(2) Uani 1 1 d . . . . .
H20A H 0.928438 0.915595 1.016309 0.031 Uiso 1 1 calc R U . . .
O1B O 0.41275(6) 0.85009(6) 0.21784(6) 0.02555(16) Uani 1 1 d . . . . .
O2B O 0.51503(6) 0.73469(7) 0.18169(6) 0.02655(16) Uani 1 1 d . . . . .
N1B N 0.43106(8) 0.80561(8) 0.52602(7) 0.02344(18) Uani 1 1 d . . . . .
N2B N 0.42491(7) 0.81795(7) 0.42170(7) 0.02176(17) Uani 1 1 d . . . . .
N3B N 0.86815(9) 0.37890(9) 0.57516(8) 0.0342(2) Uani 1 1 d . . . . .
C1B C 0.47923(8) 0.76746(8) 0.36168(8) 0.02164(19) Uani 1 1 d . . . . .
C2B C 0.54536(9) 0.70026(9) 0.40013(8) 0.0230(2) Uani 1 1 d . . . . .
C3B C 0.59774(9) 0.64099(9) 0.43499(8) 0.0234(2) Uani 1 1 d . . . . .
C4B C 0.66288(8) 0.57176(8) 0.47122(8) 0.0232(2) Uani 1 1 d . . . . .
C5B C 0.67326(9) 0.54914(9) 0.57915(8) 0.0244(2) Uani 1 1 d . . . . .
H5B H 0.634386 0.578965 0.629936 0.029 Uiso 1 1 calc R U . . .
C6B C 0.73894(9) 0.48429(9) 0.61333(8) 0.0254(2) Uani 1 1 d . . . . .
H6B H 0.744073 0.469992 0.687140 0.031 Uiso 1 1 calc R U . . .
C7B C 0.79858(9) 0.43886(9) 0.54070(9) 0.0254(2) Uani 1 1 d . . . . .
C8B C 0.78489(10) 0.45862(9) 0.43166(9) 0.0282(2) Uani 1 1 d . . . . .
H8B H 0.821654 0.426996 0.380417 0.034 Uiso 1 1 calc R U . . .
C9B C 0.71872(10) 0.52336(9) 0.39837(8) 0.0273(2) Uani 1 1 d . . . . .
H9B H 0.710820 0.535418 0.324425 0.033 Uiso 1 1 calc R U . . .
C10B C 0.87312(12) 0.35151(12) 0.68632(10) 0.0385(3) Uani 1 1 d . . . . .
H10D H 0.893902 0.422014 0.729306 0.058 Uiso 1 1 calc R U . . .
H10E H 0.931539 0.314667 0.697744 0.058 Uiso 1 1 calc R U . . .
H10F H 0.797298 0.299250 0.707328 0.058 Uiso 1 1 calc R U . . .
C11B C 0.92396(10) 0.32760(10) 0.49930(10) 0.0340(2) Uani 1 1 d . . . . .
H11D H 0.864877 0.268874 0.457075 0.051 Uiso 1 1 calc R U . . .
H11E H 0.973569 0.292386 0.537513 0.051 Uiso 1 1 calc R U . . .
H11F H 0.971176 0.386871 0.452008 0.051 Uiso 1 1 calc R U . . .
C12B C 0.47188(8) 0.78123(8) 0.24526(8) 0.02151(19) Uani 1 1 d . . . . .
C13B C 0.40484(10) 0.86974(10) 0.10504(8) 0.0276(2) Uani 1 1 d . . . . .
H13C H 0.354628 0.799211 0.068058 0.033 Uiso 1 1 calc R U . . .
H13D H 0.482526 0.893456 0.073571 0.033 Uiso 1 1 calc R U . . .
C14B C 0.35350(11) 0.96365(10) 0.09521(9) 0.0330(2) Uani 1 1 d . . . . .
H14D H 0.342761 0.978182 0.019796 0.049 Uiso 1 1 calc R U . . .
H14E H 0.405819 1.033672 0.129585 0.049 Uiso 1 1 calc R U . . .
H14F H 0.278445 0.940299 0.129856 0.049 Uiso 1 1 calc R U . . .
C15B C 0.37658(8) 0.86015(9) 0.59390(8) 0.0229(2) Uani 1 1 d . . . . .
C16B C 0.33084(9) 0.94224(9) 0.55683(9) 0.0269(2) Uani 1 1 d . . . . .
H16B H 0.336276 0.962904 0.483950 0.032 Uiso 1 1 calc R U . . .
C17B C 0.27731(10) 0.99339(10) 0.62753(10) 0.0315(2) Uani 1 1 d . . . . .
H17B H 0.245628 1.048901 0.602313 0.038 Uiso 1 1 calc R U . . .
C18B C 0.26925(10) 0.96490(10) 0.73438(10) 0.0334(2) Uani 1 1 d . . . . .
H18B H 0.232473 1.000464 0.782124 0.040 Uiso 1 1 calc R U . . .
C19B C 0.31570(10) 0.88369(10) 0.77047(9) 0.0321(2) Uani 1 1 d . . . . .
H19B H 0.310995 0.864030 0.843600 0.038 Uiso 1 1 calc R U . . .
C20B C 0.36900(9) 0.83075(10) 0.70109(8) 0.0268(2) Uani 1 1 d . . . . .
H20B H 0.400085 0.774881 0.726513 0.032 Uiso 1 1 calc R U . . .
H1B H 0.4734(13) 0.7649(13) 0.5541(12) 0.038(4) Uiso 1 1 d . . . . .
H1A H 0.6441(13) 0.7363(13) 1.0542(11) 0.034(3) Uiso 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
O1A C12A 1.3365(13) . ?
O1A C13A 1.4535(12) . ?
O2A C12A 1.2097(13) . ?
N1A N2A 1.3253(12) . ?
N1A C15A 1.3990(13) . ?
N1A H1A 0.881(15) . ?
N2A C1A 1.3093(13) . ?
N3A C7A 1.3678(14) . ?
N3A C10A 1.4497(15) . ?
N3A C11A 1.4483(16) . ?
C1A C2A 1.4232(14) . ?
C1A C12A 1.4788(14) . ?
C2A C3A 1.2061(16) . ?
C3A C4A 1.4268(15) . ?
C4A C5A 1.4044(14) . ?
C4A C9A 1.4018(14) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.3793(15) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.4112(15) . ?
C7A C8A 1.4138(14) . ?
C8A H8A 0.9500 . ?
C8A C9A 1.3795(15) . ?
C9A H9A 0.9500 . ?
C10A H10A 0.9800 . ?
C10A H10B 0.9800 . ?
C10A H10C 0.9800 . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11C 0.9800 . ?
C13A H13A 0.9900 . ?
C13A H13B 0.9900 . ?
C13A C14A 1.5006(17) . ?
C14A H14A 0.9800 . ?
C14A H14B 0.9800 . ?
C14A H14C 0.9800 . ?
C15A C16A 1.3932(14) . ?
C15A C20A 1.3932(15) . ?
C16A H16A 0.9500 . ?
C16A C17A 1.3851(14) . ?
C17A H17A 0.9500 . ?
C17A C18A 1.3893(16) . ?
C18A H18A 0.9500 . ?
C18A C19A 1.3878(15) . ?
C19A H19A 0.9500 . ?
C19A C20A 1.3897(15) . ?
C20A H20A 0.9500 . ?
O1B C12B 1.3358(12) . ?
O1B C13B 1.4464(12) . ?
O2B C12B 1.2137(12) . ?
N1B N2B 1.3243(12) . ?
N1B C15B 1.3992(13) . ?
N1B H1B 0.905(16) . ?
N2B C1B 1.3061(13) . ?
N3B C7B 1.3727(13) . ?
N3B C10B 1.4441(15) . ?
N3B C11B 1.4495(15) . ?
C1B C2B 1.4246(14) . ?
C1B C12B 1.4782(13) . ?
C2B C3B 1.2060(15) . ?
C3B C4B 1.4262(14) . ?
C4B C5B 1.3983(14) . ?
C4B C9B 1.4033(15) . ?
C5B H5B 0.9500 . ?
C5B C6B 1.3806(14) . ?
C6B H6B 0.9500 . ?
C6B C7B 1.4108(15) . ?
C7B C8B 1.4097(15) . ?
C8B H8B 0.9500 . ?
C8B C9B 1.3809(15) . ?
C9B H9B 0.9500 . ?
C10B H10D 0.9800 . ?
C10B H10E 0.9800 . ?
C10B H10F 0.9800 . ?
C11B H11D 0.9800 . ?
C11B H11E 0.9800 . ?
C11B H11F 0.9800 . ?
C13B H13C 0.9900 . ?
C13B H13D 0.9900 . ?
C13B C14B 1.5039(15) . ?
C14B H14D 0.9800 . ?
C14B H14E 0.9800 . ?
C14B H14F 0.9800 . ?
C15B C16B 1.3953(15) . ?
C15B C20B 1.3941(14) . ?
C16B H16B 0.9500 . ?
C16B C17B 1.3878(15) . ?
C17B H17B 0.9500 . ?
C17B C18B 1.3874(17) . ?
C18B H18B 0.9500 . ?
C18B C19B 1.3873(18) . ?
C19B H19B 0.9500 . ?
C19B C20B 1.3892(15) . ?
C20B H20B 0.9500 . ?

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
C12A O1A C13A 116.39(8) . . ?
N2A N1A C15A 120.13(9) . . ?
N2A N1A H1A 121.1(9) . . ?
C15A N1A H1A 118.7(9) . . ?
C1A N2A N1A 117.07(9) . . ?
C7A N3A C10A 120.48(10) . . ?
C7A N3A C11A 120.15(10) . . ?
C11A N3A C10A 119.15(10) . . ?
N2A C1A C2A 124.09(9) . . ?
N2A C1A C12A 118.06(9) . . ?
C2A C1A C12A 117.84(9) . . ?
C3A C2A C1A 175.02(11) . . ?
C2A C3A C4A 177.59(11) . . ?
C5A C4A C3A 121.05(9) . . ?
C9A C4A C3A 121.03(9) . . ?
C9A C4A C5A 117.88(10) . . ?
C4A C5A H5A 119.3 . . ?
C6A C5A C4A 121.40(10) . . ?
C6A C5A H5A 119.3 . . ?
C5A C6A H6A 119.5 . . ?
C5A C6A C7A 120.98(9) . . ?
C7A C6A H6A 119.5 . . ?
N3A C7A C6A 121.64(10) . . ?
N3A C7A C8A 121.03(10) . . ?
C6A C7A C8A 117.33(10) . . ?
C7A C8A H8A 119.3 . . ?
C9A C8A C7A 121.30(10) . . ?
C9A C8A H8A 119.3 . . ?
C4A C9A H9A 119.5 . . ?
C8A C9A C4A 121.07(9) . . ?
C8A C9A H9A 119.5 . . ?
N3A C10A H10A 109.5 . . ?
N3A C10A H10B 109.5 . . ?
N3A C10A H10C 109.5 . . ?
H10A C10A H10B 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
N3A C11A H11A 109.5 . . ?
N3A C11A H11B 109.5 . . ?
N3A C11A H11C 109.5 . . ?
H11A C11A H11B 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
O1A C12A C1A 113.72(8) . . ?
O2A C12A O1A 124.00(9) . . ?
O2A C12A C1A 122.27(10) . . ?
O1A C13A H13A 110.2 . . ?
O1A C13A H13B 110.2 . . ?
O1A C13A C14A 107.40(9) . . ?
H13A C13A H13B 108.5 . . ?
C14A C13A H13A 110.2 . . ?
C14A C13A H13B 110.2 . . ?
C13A C14A H14A 109.5 . . ?
C13A C14A H14B 109.5 . . ?
C13A C14A H14C 109.5 . . ?
H14A C14A H14B 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C16A C15A N1A 118.09(9) . . ?
C20A C15A N1A 121.58(9) . . ?
C20A C15A C16A 120.33(9) . . ?
C15A C16A H16A 120.2 . . ?
C17A C16A C15A 119.55(10) . . ?
C17A C16A H16A 120.2 . . ?
C16A C17A H17A 119.7 . . ?
C16A C17A C18A 120.57(10) . . ?
C18A C17A H17A 119.7 . . ?
C17A C18A H18A 120.2 . . ?
C19A C18A C17A 119.60(10) . . ?
C19A C18A H18A 120.2 . . ?
C18A C19A H19A 119.7 . . ?
C18A C19A C20A 120.52(10) . . ?
C20A C19A H19A 119.7 . . ?
C15A C20A H20A 120.3 . . ?
C19A C20A C15A 119.41(10) . . ?
C19A C20A H20A 120.3 . . ?
C12B O1B C13B 115.66(8) . . ?
N2B N1B C15B 120.05(8) . . ?
N2B N1B H1B 120.4(9) . . ?
C15B N1B H1B 119.5(9) . . ?
C1B N2B N1B 117.85(8) . . ?
C7B N3B C10B 120.34(10) . . ?
C7B N3B C11B 120.49(10) . . ?
C10B N3B C11B 118.55(9) . . ?
N2B C1B C2B 124.81(9) . . ?
N2B C1B C12B 117.66(8) . . ?
C2B C1B C12B 117.52(8) . . ?
C3B C2B C1B 177.46(11) . . ?
C2B C3B C4B 177.04(11) . . ?
C5B C4B C3B 121.88(9) . . ?
C5B C4B C9B 117.69(9) . . ?
C9B C4B C3B 120.43(9) . . ?
C4B C5B H5B 119.4 . . ?
C6B C5B C4B 121.26(10) . . ?
C6B C5B H5B 119.4 . . ?
C5B C6B H6B 119.4 . . ?
C5B C6B C7B 121.24(9) . . ?
C7B C6B H6B 119.4 . . ?
N3B C7B C6B 121.18(10) . . ?
N3B C7B C8B 121.45(10) . . ?
C8B C7B C6B 117.37(9) . . ?
C7B C8B H8B 119.6 . . ?
C9B C8B C7B 120.86(10) . . ?
C9B C8B H8B 119.6 . . ?
C4B C9B H9B 119.2 . . ?
C8B C9B C4B 121.53(10) . . ?
C8B C9B H9B 119.2 . . ?
N3B C10B H10D 109.5 . . ?
N3B C10B H10E 109.5 . . ?
N3B C10B H10F 109.5 . . ?
H10D C10B H10E 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
N3B C11B H11D 109.5 . . ?
N3B C11B H11E 109.5 . . ?
N3B C11B H11F 109.5 . . ?
H11D C11B H11E 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
O1B C12B C1B 112.78(8) . . ?
O2B C12B O1B 123.82(9) . . ?
O2B C12B C1B 123.40(9) . . ?
O1B C13B H13C 110.5 . . ?
O1B C13B H13D 110.5 . . ?
O1B C13B C14B 105.93(8) . . ?
H13C C13B H13D 108.7 . . ?
C14B C13B H13C 110.5 . . ?
C14B C13B H13D 110.5 . . ?
C13B C14B H14D 109.5 . . ?
C13B C14B H14E 109.5 . . ?
C13B C14B H14F 109.5 . . ?
H14D C14B H14E 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
C16B C15B N1B 121.69(9) . . ?
C20B C15B N1B 118.25(9) . . ?
C20B C15B C16B 120.06(9) . . ?
C15B C16B H16B 120.3 . . ?
C17B C16B C15B 119.31(10) . . ?
C17B C16B H16B 120.3 . . ?
C16B C17B H17B 119.4 . . ?
C18B C17B C16B 121.17(10) . . ?
C18B C17B H17B 119.4 . . ?
C17B C18B H18B 120.5 . . ?
C17B C18B C19B 119.01(10) . . ?
C19B C18B H18B 120.5 . . ?
C18B C19B H19B 119.6 . . ?
C18B C19B C20B 120.87(10) . . ?
C20B C19B H19B 119.6 . . ?
C15B C20B H20B 120.2 . . ?
C19B C20B C15B 119.57(10) . . ?
C19B C20B H20B 120.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1B H1B O2A 0.905(16) 2.173(15) 2.9495(11) 143.4(13) . yes
N1A H1A O2B 0.881(15) 2.273(15) 3.0206(11) 142.6(12) 1_556 yes

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
N1A N2A C1A C2A -0.66(14) . . . . ?
N1A N2A C1A C12A -179.84(8) . . . . ?
N1A C15A C16A C17A -179.88(9) . . . . ?
N1A C15A C20A C19A 179.10(9) . . . . ?
N2A N1A C15A C16A -168.69(9) . . . . ?
N2A N1A C15A C20A 11.72(14) . . . . ?
N2A C1A C12A O1A 7.17(13) . . . . ?
N2A C1A C12A O2A -174.53(10) . . . . ?
N3A C7A C8A C9A 178.12(10) . . . . ?
C2A C1A C12A O1A -172.06(9) . . . . ?
C2A C1A C12A O2A 6.24(15) . . . . ?
C3A C4A C5A C6A 175.94(10) . . . . ?
C3A C4A C9A C8A -176.47(9) . . . . ?
C4A C5A C6A C7A 0.54(16) . . . . ?
C5A C4A C9A C8A 1.32(15) . . . . ?
C5A C6A C7A N3A -178.64(10) . . . . ?
C5A C6A C7A C8A 1.26(15) . . . . ?
C6A C7A C8A C9A -1.78(15) . . . . ?
C7A C8A C9A C4A 0.50(15) . . . . ?
C9A C4A C5A C6A -1.84(15) . . . . ?
C10A N3A C7A C6A 2.48(16) . . . . ?
C10A N3A C7A C8A -177.42(10) . . . . ?
C11A N3A C7A C6A 177.07(11) . . . . ?
C11A N3A C7A C8A -2.83(16) . . . . ?
C12A O1A C13A C14A -148.70(9) . . . . ?
C13A O1A C12A O2A 1.70(15) . . . . ?
C13A O1A C12A C1A 179.97(9) . . . . ?
C15A N1A N2A C1A 178.18(9) . . . . ?
C15A C16A C17A C18A 0.35(15) . . . . ?
C16A C15A C20A C19A -0.48(15) . . . . ?
C16A C17A C18A C19A 0.35(16) . . . . ?
C17A C18A C19A C20A -1.13(16) . . . . ?
C18A C19A C20A C15A 1.19(16) . . . . ?
C20A C15A C16A C17A -0.29(15) . . . . ?
N1B N2B C1B C2B -0.32(15) . . . . ?
N1B N2B C1B C12B 179.85(8) . . . . ?
N1B C15B C16B C17B 179.77(9) . . . . ?
N1B C15B C20B C19B 179.81(10) . . . . ?
N2B N1B C15B C16B -10.33(14) . . . . ?
N2B N1B C15B C20B 169.86(9) . . . . ?
N2B C1B C12B O1B 2.89(13) . . . . ?
N2B C1B C12B O2B -177.05(9) . . . . ?
N3B C7B C8B C9B -177.12(10) . . . . ?
C2B C1B C12B O1B -176.95(8) . . . . ?
C2B C1B C12B O2B 3.11(14) . . . . ?
C3B C4B C5B C6B -178.39(9) . . . . ?
C3B C4B C9B C8B 178.21(10) . . . . ?
C4B C5B C6B C7B 0.33(16) . . . . ?
C5B C4B C9B C8B -2.06(16) . . . . ?
C5B C6B C7B N3B 176.94(10) . . . . ?
C5B C6B C7B C8B -2.35(15) . . . . ?
C6B C7B C8B C9B 2.17(16) . . . . ?
C7B C8B C9B C4B 0.02(17) . . . . ?
C9B C4B C5B C6B 1.88(15) . . . . ?
C10B N3B C7B C6B 5.96(17) . . . . ?
C10B N3B C7B C8B -174.77(11) . . . . ?
C11B N3B C7B C6B 176.73(10) . . . . ?
C11B N3B C7B C8B -4.01(17) . . . . ?
C12B O1B C13B C14B -170.59(9) . . . . ?
C13B O1B C12B O2B -1.63(14) . . . . ?
C13B O1B C12B C1B 178.43(8) . . . . ?
C15B N1B N2B C1B 178.54(9) . . . . ?
C15B C16B C17B C18B 0.45(17) . . . . ?
C16B C15B C20B C19B 0.00(15) . . . . ?
C16B C17B C18B C19B -0.04(17) . . . . ?
C17B C18B C19B C20B -0.40(17) . . . . ?
C18B C19B C20B C15B 0.42(17) . . . . ?
C20B C15B C16B C17B -0.43(15) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id DS-dma-v
_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 1.139
_oxdiff_exptl_absorpt_empirical_full_min 0.862
####################################################################### 
# 
# 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_ia723a
_database_code_depnum_ccdc_archive 'CCDC 2331032'
loop_
_audit_author_name
_audit_author_address
'Richard J Staples'
;Dartmouth College
United States of America
;
_audit_update_record             
;
2024-02-05 deposited with the CCDC.	2025-06-05 downloaded from the CCDC.
;
_audit_creation_date             2023-07-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H15 N3 O4'
_chemical_formula_sum            'C18 H15 N3 O4'
_chemical_formula_weight         337.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         C18H15N3O4
_chemical_oxdiff_usercomment     'DS-ben alk no-1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   19.7442(3)
_cell_length_b                   6.98090(10)
_cell_length_c                   11.8207(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.3230(10)
_cell_angle_gamma                90
_cell_volume                     1626.53(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10587
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.4640
_cell_measurement_theta_min      4.5020
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.827
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.416
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
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    1.378
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             704
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.0067
-1 0 0 0.0230
0 1 1 0.0909
-1 4 -4 0.0984
1 0 8 0.0938
0 -5 0 0.0783
-1 0 -8 0.1321

_exptl_crystal_recrystallization_method 'used as recieved'
_exptl_crystal_size_max          0.236
_exptl_crystal_size_mid          0.188
_exptl_crystal_size_min          0.03
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0000 -0.0002 -0.0002 -0.0626 -0.0456 0.0109
-1.0000 0.0002 0.0002 0.0626 0.0456 -0.0109
-0.0009 1.0011 0.9935 0.1192 -0.1319 0.1844
-1.0404 3.8852 -3.8573 0.6272 -0.7340 -0.2605
1.2696 0.0818 7.5801 -0.1665 0.1933 0.9669
0.4499 -4.5286 -0.0292 -0.6249 0.7323 -0.2708
-1.2673 -0.1030 -7.5796 0.1636 -0.1899 -0.9681

_exptl_special_details           
;
Data was collected using a Rigaku Synergy S Diffractometer diffractometer equipped 
with an Oxford 800 low-temperature apparatus.  A suitable 
crystal was chosen and mounted on a nylon loop using Paratone oil.  Data  were 
measured based on the Pre-Experiment plugin of CrysAlisPro software.  Cell 
parameters were retrieved using CrysAlisPro software and data reduction was 
performed using the intergration software inside the CrysAlisPro which 
corrects for Lp.  The structure was solved by the direct method using the 
SHELXT program and refined by least squares method on F2, SHELXL,
 incorporated in OLEX2. 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            16712
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.338
_diffrn_reflns_theta_min         2.241
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -79.00   1.00   0.50    0.43    --  -46.85 104.00 179.00  160
  2  ω     20.00  82.00   0.50    0.43    --   46.85-104.00  77.00  124
  3  ω   -162.00 -86.00   0.50    1.74    --  -91.75-104.00  77.00  152
  4  ω    -79.00 -21.00   0.50    1.74    --  -91.75 104.00 179.00  116
  5  ω     43.00 105.00   0.50    1.74    --  113.25-104.00  77.00  124
  6  ω    108.00 178.00   0.50    1.74    --  113.25 104.00 179.00  140
  7  ω    -39.00  29.00   0.50    0.43    --  -46.85  19.00 120.00  136
  8  ω    -47.00  26.00   0.50    0.43    --  -46.85  37.00 -30.00  146
  9  ω    -27.00  38.00   0.50    0.43    --   46.85 -19.00  60.00  130
 10  ω    -27.00  38.00   0.50    0.43    --   46.85 -19.00-180.00  130
 11  ω     36.00  93.00   0.50    0.43    --   46.85-125.00-180.00  114
 12  ω    -53.00 -20.00   0.50    1.74    --  -91.75  45.00 -30.00   66
 13  ω     42.00  69.00   0.50    1.74    --  113.25 -61.00   0.00   54
 14  ω     42.00  69.00   0.50    1.74    --  113.25 -61.00 -90.00   54
 15  ω     42.00  69.00   0.50    1.74    --  113.25 -61.00 -60.00   54
 16  ω     44.00 108.00   0.50    1.74    --  113.25-125.00-150.00  128
 17  ω    100.00 178.00   0.50    1.74    --  113.25  15.00 -90.00  156
 18  ω     42.00  69.00   0.50    1.74    --  113.25 -61.00  90.00   54
 19  ω     42.00  94.00   0.50    1.74    --  113.25 -77.00  90.00  104
 20  ω     42.00  94.00   0.50    1.74    --  113.25 -77.00 -90.00  104
 21  ω     42.00  69.00   0.50    1.74    --  113.25 -61.00 120.00   54
 22  ω     42.00  69.00   0.50    1.74    --  113.25 -61.00-180.00   54
 23  ω     42.00 104.00   0.50    1.74    --  113.25 -94.00 150.00  124
 24  ω     42.00  94.00   0.50    1.74    --  113.25 -77.00   0.00  104
 25  ω     42.00  94.00   0.50    1.74    --  113.25 -77.00-180.00  104
 26  ω    101.00 178.00   0.50    1.74    --  113.25  30.00 -90.00  154
 27  ω     42.00 104.00   0.50    1.74    --  113.25 -94.00  90.00  124
 28  ω     42.00  69.00   0.50    1.74    --  113.25 -61.00 -30.00   54
 29  ω    110.00 178.00   0.50    1.74    --  113.25  77.00-150.00  136
 30  ω     54.00  89.00   0.50    1.74    --  113.25 -77.00 150.00   70
 31  ω     42.00  69.00   0.50    1.74    --  113.25 -61.00-150.00   54
 32  ω     43.00  68.00   0.50    1.74    --  113.25 -61.00-120.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0625691000
_diffrn_orient_matrix_UB_12      0.1318505000
_diffrn_orient_matrix_UB_13      -0.0129142000
_diffrn_orient_matrix_UB_21      -0.0455817000
_diffrn_orient_matrix_UB_22      -0.1664534000
_diffrn_orient_matrix_UB_23      0.0349344000
_diffrn_orient_matrix_UB_31      0.0109922000
_diffrn_orient_matrix_UB_32      0.0600751000
_diffrn_orient_matrix_UB_33      0.1250676000
_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_current           1
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3071
_reflns_number_total             3476
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3476
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0394
_refine_ls_restrained_S_all      1.053
_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)+(0.0644P)²+0.5193P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1089
_refine_ls_wR_factor_ref         0.1136
_refine_special_details          
;
The structure was refined by Least Squares SHELXL incorporated 
in Olex2 software program. All non-hydrogen atoms were refined anisotropically. 
Hydrogen atom positions were calculated geometrically and refined using the 
riding model, except for the hydrogen atom on the non-carbon atom(s) which were found 
by difference Fourier methods and refined isotropically when data permits.
;
_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 Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C14(H14), C15(H15), C17(H17),
 C18(H18)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.22533(4) 0.46714(12) 0.27540(6) 0.0196(2) Uani 1 1 d . . . . .
O2 O 0.32888(5) 0.53378(16) 0.21769(7) 0.0313(2) Uani 1 1 d . . . . .
O3 O 0.69756(4) 0.89502(15) 0.57708(7) 0.0282(2) Uani 1 1 d . . . . .
O4 O 0.66824(5) 0.97666(16) 0.74402(7) 0.0303(2) Uani 1 1 d . . . . .
N1 N 0.38559(5) 0.70382(15) 0.53718(8) 0.0183(2) Uani 1 1 d . . . . .
H1 H 0.3552(9) 0.719(2) 0.5877(13) 0.026(4) Uiso 1 1 d . . . . .
N2 N 0.36691(5) 0.64420(14) 0.43278(7) 0.0174(2) Uani 1 1 d . . . . .
N3 N 0.65498(5) 0.91203(15) 0.64800(8) 0.0199(2) Uani 1 1 d . . . . .
C1 C 0.30383(6) 0.59631(16) 0.41005(9) 0.0175(2) Uani 1 1 d . . . . .
C2 C 0.28861(6) 0.53014(17) 0.29057(9) 0.0186(2) Uani 1 1 d . . . . .
C3 C 0.25137(6) 0.60123(17) 0.48805(9) 0.0187(2) Uani 1 1 d . . . . .
C4 C 0.20713(6) 0.60400(17) 0.55348(9) 0.0191(2) Uani 1 1 d . . . . .
C5 C 0.15351(6) 0.60637(16) 0.63033(10) 0.0181(2) Uani 1 1 d . . . . .
C6 C 0.08535(6) 0.61462(17) 0.58879(10) 0.0213(3) Uani 1 1 d . . . . .
H6 H 0.074564 0.618252 0.509442 0.026 Uiso 1 1 calc R U . . .
C7 C 0.03397(6) 0.61745(19) 0.66385(11) 0.0257(3) Uani 1 1 d . . . . .
H7 H -0.012047 0.623653 0.635773 0.031 Uiso 1 1 calc R U . . .
C8 C 0.04946(7) 0.61125(19) 0.78012(11) 0.0262(3) Uani 1 1 d . . . . .
H8 H 0.014087 0.613887 0.831265 0.031 Uiso 1 1 calc R U . . .
C9 C 0.11664(6) 0.60119(18) 0.82133(10) 0.0236(3) Uani 1 1 d . . . . .
H9 H 0.127042 0.595555 0.900743 0.028 Uiso 1 1 calc R U . . .
C10 C 0.16866(6) 0.59932(17) 0.74751(10) 0.0200(2) Uani 1 1 d . . . . .
H10 H 0.214536 0.593254 0.776327 0.024 Uiso 1 1 calc R U . . .
C11 C 0.20570(6) 0.40023(18) 0.16138(9) 0.0210(3) Uani 1 1 d . . . . .
H11A H 0.227693 0.276036 0.146483 0.025 Uiso 1 1 calc R U . . .
H11B H 0.219386 0.494257 0.104308 0.025 Uiso 1 1 calc R U . . .
C12 C 0.12970(6) 0.37821(19) 0.15595(11) 0.0244(3) Uani 1 1 d . . . . .
H12A H 0.114003 0.333230 0.080384 0.037 Uiso 1 1 calc R U . . .
H12B H 0.108695 0.502115 0.170990 0.037 Uiso 1 1 calc R U . . .
H12C H 0.116962 0.284961 0.212928 0.037 Uiso 1 1 calc R U . . .
C13 C 0.45289(6) 0.75319(16) 0.56327(9) 0.0168(2) Uani 1 1 d . . . . .
C14 C 0.47143(6) 0.81720(17) 0.67280(9) 0.0185(2) Uani 1 1 d . . . . .
H14 H 0.438504 0.825909 0.728076 0.022 Uiso 1 1 calc R U . . .
C15 C 0.53809(6) 0.86768(17) 0.69996(9) 0.0183(2) Uani 1 1 d . . . . .
H15 H 0.551354 0.911318 0.774082 0.022 Uiso 1 1 calc R U . . .
C16 C 0.58551(6) 0.85413(16) 0.61808(9) 0.0172(2) Uani 1 1 d . . . . .
C17 C 0.56807(6) 0.79047(17) 0.50889(9) 0.0187(2) Uani 1 1 d . . . . .
H17 H 0.601201 0.782645 0.453903 0.022 Uiso 1 1 calc R U . . .
C18 C 0.50165(6) 0.73888(17) 0.48202(8) 0.0180(2) Uani 1 1 d . . . . .
H18 H 0.488861 0.693427 0.408092 0.022 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.3268(14) . ?
O1 C11 1.4575(13) . ?
O2 C2 1.2061(15) . ?
O3 N3 1.2270(13) . ?
O4 N3 1.2353(13) . ?
N1 H1 0.878(17) . ?
N1 N2 1.3340(13) . ?
N1 C13 1.3900(15) . ?
N2 C1 1.3023(15) . ?
N3 C16 1.4538(14) . ?
C1 C2 1.4997(15) . ?
C1 C3 1.4264(15) . ?
C3 C4 1.2001(17) . ?
C4 C5 1.4345(16) . ?
C5 C6 1.4066(16) . ?
C5 C10 1.4009(16) . ?
C6 H6 0.9500 . ?
C6 C7 1.3862(17) . ?
C7 H7 0.9500 . ?
C7 C8 1.3912(18) . ?
C8 H8 0.9500 . ?
C8 C9 1.3882(18) . ?
C9 H9 0.9500 . ?
C9 C10 1.3857(16) . ?
C10 H10 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.5060(16) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.3983(15) . ?
C13 C18 1.4023(15) . ?
C14 H14 0.9500 . ?
C14 C15 1.3821(16) . ?
C15 H15 0.9500 . ?
C15 C16 1.3883(16) . ?
C16 C17 1.3894(15) . ?
C17 H17 0.9500 . ?
C17 C18 1.3793(16) . ?
C18 H18 0.9500 . ?

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 O1 C11 115.41(8) . . ?
N2 N1 H1 120.3(10) . . ?
N2 N1 C13 119.48(9) . . ?
C13 N1 H1 120.2(10) . . ?
C1 N2 N1 118.73(10) . . ?
O3 N3 O4 123.09(10) . . ?
O3 N3 C16 118.76(9) . . ?
O4 N3 C16 118.15(9) . . ?
N2 C1 C2 114.23(10) . . ?
N2 C1 C3 125.59(10) . . ?
C3 C1 C2 120.18(10) . . ?
O1 C2 C1 111.42(9) . . ?
O2 C2 O1 124.40(10) . . ?
O2 C2 C1 124.18(11) . . ?
C4 C3 C1 179.52(13) . . ?
C3 C4 C5 179.12(12) . . ?
C6 C5 C4 120.37(10) . . ?
C10 C5 C4 120.17(11) . . ?
C10 C5 C6 119.46(11) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 C5 119.86(11) . . ?
C7 C6 H6 120.1 . . ?
C6 C7 H7 119.8 . . ?
C6 C7 C8 120.32(11) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 119.94(11) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.50(11) . . ?
C10 C9 H9 119.8 . . ?
C5 C10 H10 120.0 . . ?
C9 C10 C5 119.91(11) . . ?
C9 C10 H10 120.0 . . ?
O1 C11 H11A 110.4 . . ?
O1 C11 H11B 110.4 . . ?
O1 C11 C12 106.44(9) . . ?
H11A C11 H11B 108.6 . . ?
C12 C11 H11A 110.4 . . ?
C12 C11 H11B 110.4 . . ?
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 . . ?
N1 C13 C14 118.71(10) . . ?
N1 C13 C18 121.05(10) . . ?
C14 C13 C18 120.24(10) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 C13 119.42(10) . . ?
C15 C14 H14 120.3 . . ?
C14 C15 H15 120.3 . . ?
C14 C15 C16 119.49(10) . . ?
C16 C15 H15 120.3 . . ?
C15 C16 N3 118.44(10) . . ?
C15 C16 C17 121.92(10) . . ?
C17 C16 N3 119.63(10) . . ?
C16 C17 H17 120.7 . . ?
C18 C17 C16 118.59(10) . . ?
C18 C17 H17 120.7 . . ?
C13 C18 H18 119.8 . . ?
C17 C18 C13 120.34(10) . . ?
C17 C18 H18 119.8 . . ?

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
O3 N3 C16 C15 177.85(11) . . . . ?
O3 N3 C16 C17 -3.27(17) . . . . ?
O4 N3 C16 C15 -2.31(16) . . . . ?
O4 N3 C16 C17 176.57(11) . . . . ?
N1 N2 C1 C2 -179.57(10) . . . . ?
N1 N2 C1 C3 -0.11(18) . . . . ?
N1 C13 C14 C15 -179.70(11) . . . . ?
N1 C13 C18 C17 179.27(11) . . . . ?
N2 N1 C13 C14 179.37(10) . . . . ?
N2 N1 C13 C18 -0.86(17) . . . . ?
N2 C1 C2 O1 174.32(10) . . . . ?
N2 C1 C2 O2 -5.64(18) . . . . ?
N3 C16 C17 C18 -179.09(10) . . . . ?
C2 O1 C11 C12 -167.61(10) . . . . ?
C3 C1 C2 O1 -5.17(15) . . . . ?
C3 C1 C2 O2 174.87(12) . . . . ?
C4 C5 C6 C7 -179.80(11) . . . . ?
C4 C5 C10 C9 -179.85(11) . . . . ?
C5 C6 C7 C8 -0.31(19) . . . . ?
C6 C5 C10 C9 -0.23(17) . . . . ?
C6 C7 C8 C9 -0.3(2) . . . . ?
C7 C8 C9 C10 0.7(2) . . . . ?
C8 C9 C10 C5 -0.41(19) . . . . ?
C10 C5 C6 C7 0.58(18) . . . . ?
C11 O1 C2 O2 -0.26(17) . . . . ?
C11 O1 C2 C1 179.78(9) . . . . ?
C13 N1 N2 C1 179.19(10) . . . . ?
C13 C14 C15 C16 0.04(17) . . . . ?
C14 C13 C18 C17 -0.97(17) . . . . ?
C14 C15 C16 N3 178.68(10) . . . . ?
C14 C15 C16 C17 -0.18(18) . . . . ?
C15 C16 C17 C18 -0.25(18) . . . . ?
C16 C17 C18 C13 0.82(17) . . . . ?
C18 C13 C14 C15 0.53(17) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id 'DS-ben alk no-1'
_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 1.784
_oxdiff_exptl_absorpt_empirical_full_min 0.738
####################################################################### 
# 
# 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_ia723c
_database_code_depnum_ccdc_archive 'CCDC 2331028'
loop_
_audit_author_name
_audit_author_address
'Richard J Staples'
;Dartmouth College
United States of America
;
_audit_update_record             
;
2024-02-05 deposited with the CCDC.	2025-06-05 downloaded from the CCDC.
;
_audit_creation_date             2023-07-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H19 N3 O4 Si'
_chemical_formula_sum            'C15 H19 N3 O4 Si'
_chemical_formula_weight         333.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15H19N3O4Si
_chemical_oxdiff_usercomment     'DS-Si alk no-1'
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'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.28950(10)
_cell_length_b                   10.21410(10)
_cell_length_c                   10.83540(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.6480(10)
_cell_angle_gamma                90
_cell_volume                     1688.72(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11410
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      80.1140
_cell_measurement_theta_min      2.8870
_shelx_estimated_absorpt_T_max   0.900
_shelx_estimated_absorpt_T_min   0.598
_exptl_absorpt_coefficient_mu    1.437
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.386
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
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    1.311
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             704
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.0553
-1 0 0 0.0200
0 -1 0 0.1027
0 1 0 0.0786
-1 0 7 0.1984
1 -3 -6 0.1561
-1 -6 2 0.0948
1 6 -2 0.1112

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.399
_exptl_crystal_size_mid          0.181
_exptl_crystal_size_min          0.075
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0000 0.0000 -0.0000 0.1008 0.0016 -0.0049
-1.0000 -0.0000 0.0000 -0.1008 -0.0016 0.0049
0.0000 -1.0000 0.0000 0.0047 -0.1438 0.0453
-0.0000 1.0000 -0.0000 -0.0047 0.1438 -0.0453
-1.2655 0.1242 7.0145 -0.0238 0.3196 0.9473
1.3271 -2.5571 -6.4592 0.0496 -0.6452 -0.7624
-0.7963 -6.3843 1.8655 -0.0227 -0.8382 0.5448
0.8241 6.3169 -2.1083 0.0222 0.8181 -0.5747

_exptl_special_details           
;
Data was collected using a Rigaku Synergy S Diffractometer diffractometer equipped 
with an Oxford 800 low-temperature apparatus.  A suitable 
crystal was chosen and mounted on a nylon loop using Paratone oil.  Data  were 
measured based on the Pre-Experiment plugin of CrysAlisPro software.  Cell 
parameters were retrieved using CrysAlisPro software and data reduction was 
performed using the intergration software inside the CrysAlisPro which 
corrects for Lp.  The structure was solved by the direct method using the 
SHELXT program and refined by least squares method on F2, SHELXL,
 incorporated in OLEX2. 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            18441
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.360
_diffrn_reflns_theta_min         2.896
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00 -20.00   0.50    0.14    --  -91.75  45.00  90.00   66
  2  ω    -53.00 -20.00   0.50    0.14    --  -91.75  45.00  60.00   66
  3  ω    -53.00 -20.00   0.50    0.14    --  -91.75  45.00 -30.00   66
  4  ω    -39.00  28.00   0.50    0.05    --  -47.10  19.00 -90.00  134
  5  ω     97.00 178.00   0.50    0.14    --  113.25 125.00 -30.00  162
  6  ω    109.00 169.00   0.50    0.14    --  113.25 101.00 143.00  120
  7  ω    110.00 178.00   0.50    0.14    --  113.25  77.00 120.00  136
  8  ω    101.00 178.00   0.50    0.14    --  113.25  30.00  60.00  154
  9  ω     97.00 178.00   0.50    0.14    --  113.25 125.00-150.00  162
 10  ω    101.00 178.00   0.50    0.14    --  113.25  45.00-120.00  154
 11  ω     42.00  69.00   0.50    0.14    --  113.25 -61.00-120.00   54
 12  ω     42.00  69.00   0.50    0.14    --  113.25 -61.00 -60.00   54
 13  ω     42.00  94.00   0.50    0.14    --  113.25 -77.00  30.00  104
 14  ω     42.00  94.00   0.50    0.14    --  113.25 -77.00  60.00  104
 15  ω     42.00  94.00   0.50    0.14    --  113.25 -77.00 150.00  104
 16  ω     42.00  69.00   0.50    0.14    --  113.25 -61.00 150.00   54
 17  ω     42.00  69.00   0.50    0.14    --  113.25 -61.00  60.00   54
 18  ω     42.00  69.00   0.50    0.14    --  113.25 -61.00  30.00   54
 19  ω     42.00  69.00   0.50    0.14    --  113.25 -61.00-180.00   54
 20  ω     42.00  69.00   0.50    0.14    --  113.25 -61.00-150.00   54
 21  ω     42.00  69.00   0.50    0.14    --  113.25 -61.00 -90.00   54
 22  ω      6.00  81.00   0.50    0.05    --   47.10-101.00  39.00  150
 23  ω     44.00 108.00   0.50    0.14    --  113.25-125.00 150.00  128
 24  ω     43.00 104.00   0.50    0.14    --  113.25-101.00  39.00  122
 25  ω     44.00 108.00   0.50    0.14    --  113.25-125.00 -90.00  128
 26  ω     44.00 108.00   0.50    0.14    --  113.25-125.00-180.00  128
 27  ω    -78.00  16.00   0.50    0.05    --  -47.10 101.00 143.00  188
 28  ω    -78.00 -21.00   0.50    0.14    --  -91.75 101.00 143.00  114
 29  ω   -120.00 -35.00   0.50    0.05    --  -47.10 -37.00 -60.00  170
 30  ω   -162.00 -87.00   0.50    0.14    --  -91.75-101.00  39.00  150
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1008194000
_diffrn_orient_matrix_UB_12      -0.0046775000
_diffrn_orient_matrix_UB_13      0.0148861000
_diffrn_orient_matrix_UB_21      0.0015703000
_diffrn_orient_matrix_UB_22      0.1437516000
_diffrn_orient_matrix_UB_23      0.0432978000
_diffrn_orient_matrix_UB_31      -0.0049348000
_diffrn_orient_matrix_UB_32      -0.0452923000
_diffrn_orient_matrix_UB_33      0.1349544000
_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_current           1
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3374
_reflns_number_total             3639
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         3639
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0355
_refine_ls_restrained_S_all      1.056
_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)+(0.0555P)²+0.5205P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.0980
_refine_special_details          
;
The structure was refined by Least Squares SHELXL incorporated 
in Olex2 software program. All non-hydrogen atoms were refined anisotropically. 
Hydrogen atom positions were calculated geometrically and refined using the 
riding model, except for the hydrogen atom on the non-carbon atom(s) which were found 
by difference Fourier methods and refined isotropically when data permits.
;
_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 Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C8(H8A,H8B,H8C)
;
_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
Si1 Si 0.10239(2) 0.34615(3) 0.69018(3) 0.01908(11) Uani 1 1 d . . . . .
O1 O 0.23996(6) 0.65962(8) 0.36395(8) 0.01997(19) Uani 1 1 d . . . . .
O2 O 0.36484(6) 0.59316(9) 0.28251(7) 0.02138(19) Uani 1 1 d . . . . .
O3 O 0.71638(6) -0.04531(10) 0.52024(9) 0.0279(2) Uani 1 1 d . . . . .
O4 O 0.65542(6) -0.13514(9) 0.67394(8) 0.0242(2) Uani 1 1 d . . . . .
N1 N 0.39415(7) 0.32928(10) 0.56259(9) 0.0175(2) Uani 1 1 d . . . . .
H1 H 0.3524(11) 0.3246(15) 0.6130(14) 0.019(4) Uiso 1 1 d . . . . .
N2 N 0.38750(6) 0.41740(10) 0.47205(8) 0.0169(2) Uani 1 1 d . . . . .
N3 N 0.65963(6) -0.04745(10) 0.59578(9) 0.0186(2) Uani 1 1 d . . . . .
C1 C 0.31555(7) 0.48619(11) 0.46141(10) 0.0167(2) Uani 1 1 d . . . . .
C2 C 0.24364(8) 0.46405(11) 0.53695(10) 0.0183(2) Uani 1 1 d . . . . .
C3 C 0.18788(8) 0.42616(12) 0.60244(11) 0.0205(2) Uani 1 1 d . . . . .
C4 C 0.07631(9) 0.45176(15) 0.82290(12) 0.0290(3) Uani 1 1 d . . . . .
H4A H 0.128707 0.461768 0.879054 0.043 Uiso 1 1 calc R U . . .
H4B H 0.029472 0.411142 0.867319 0.043 Uiso 1 1 calc R U . . .
H4C H 0.057018 0.537966 0.792226 0.043 Uiso 1 1 calc R U . . .
C5 C 0.14859(10) 0.18555(14) 0.74242(14) 0.0318(3) Uani 1 1 d . . . . .
H5A H 0.163786 0.134303 0.670380 0.048 Uiso 1 1 calc R U . . .
H5B H 0.105015 0.137789 0.787388 0.048 Uiso 1 1 calc R U . . .
H5C H 0.201294 0.199924 0.797026 0.048 Uiso 1 1 calc R U . . .
C6 C 0.00363(9) 0.32523(15) 0.58184(12) 0.0285(3) Uani 1 1 d . . . . .
H6A H -0.023397 0.410815 0.564463 0.043 Uiso 1 1 calc R U . . .
H6B H -0.038529 0.267834 0.619614 0.043 Uiso 1 1 calc R U . . .
H6C H 0.020923 0.286063 0.504498 0.043 Uiso 1 1 calc R U . . .
C7 C 0.22730(8) 0.75678(12) 0.26564(11) 0.0218(2) Uani 1 1 d . . . . .
H7A H 0.285022 0.786720 0.240096 0.026 Uiso 1 1 calc R U . . .
H7B H 0.195887 0.833568 0.296744 0.026 Uiso 1 1 calc R U . . .
C8 C 0.17529(8) 0.69916(14) 0.15587(12) 0.0255(3) Uani 1 1 d . . . . .
H8A H 0.166733 0.765769 0.091133 0.038 Uiso 1 1 calc R U . . .
H8B H 0.118137 0.669697 0.181263 0.038 Uiso 1 1 calc R U . . .
H8C H 0.207188 0.624549 0.123862 0.038 Uiso 1 1 calc R U . . .
C9 C 0.46404(7) 0.24221(11) 0.57258(10) 0.0164(2) Uani 1 1 d . . . . .
C10 C 0.46462(8) 0.14847(11) 0.66732(10) 0.0178(2) Uani 1 1 d . . . . .
H10 H 0.420371 0.149842 0.725013 0.021 Uiso 1 1 calc R U . . .
C11 C 0.52946(8) 0.05428(11) 0.67676(10) 0.0176(2) Uani 1 1 d . . . . .
H11 H 0.530116 -0.010076 0.740114 0.021 Uiso 1 1 calc R U . . .
C12 C 0.59381(7) 0.05553(11) 0.59157(10) 0.0166(2) Uani 1 1 d . . . . .
C13 C 0.59499(8) 0.14923(11) 0.49808(10) 0.0177(2) Uani 1 1 d . . . . .
H13 H 0.640072 0.148564 0.441663 0.021 Uiso 1 1 calc R U . . .
C14 C 0.52988(7) 0.24295(12) 0.48850(10) 0.0174(2) Uani 1 1 d . . . . .
H14 H 0.529744 0.307477 0.425345 0.021 Uiso 1 1 calc R U . . .
C15 C 0.31128(7) 0.58409(11) 0.35870(10) 0.0171(2) 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
Si1 C3 1.8543(13) . ?
Si1 C4 1.8611(14) . ?
Si1 C5 1.8600(14) . ?
Si1 C6 1.8650(14) . ?
O1 C7 1.4597(14) . ?
O1 C15 1.3399(14) . ?
O2 C15 1.2028(14) . ?
O3 N3 1.2304(13) . ?
O4 N3 1.2372(13) . ?
N1 H1 0.868(16) . ?
N1 N2 1.3305(13) . ?
N1 C9 1.3892(15) . ?
N2 C1 1.3042(15) . ?
N3 C12 1.4544(15) . ?
C1 C2 1.4298(16) . ?
C1 C15 1.4946(15) . ?
C2 C3 1.2070(17) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.5077(17) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.4034(16) . ?
C9 C14 1.4000(15) . ?
C10 H10 0.9500 . ?
C10 C11 1.3805(16) . ?
C11 H11 0.9500 . ?
C11 C12 1.3914(16) . ?
C12 C13 1.3945(16) . ?
C13 H13 0.9500 . ?
C13 C14 1.3803(16) . ?
C14 H14 0.9500 . ?

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 Si1 C4 109.48(6) . . ?
C3 Si1 C5 106.16(6) . . ?
C3 Si1 C6 107.26(6) . . ?
C4 Si1 C6 110.37(7) . . ?
C5 Si1 C4 111.83(7) . . ?
C5 Si1 C6 111.54(7) . . ?
C15 O1 C7 115.53(9) . . ?
N2 N1 H1 118.5(10) . . ?
N2 N1 C9 120.85(10) . . ?
C9 N1 H1 120.6(10) . . ?
C1 N2 N1 117.00(10) . . ?
O3 N3 O4 122.54(10) . . ?
O3 N3 C12 118.82(10) . . ?
O4 N3 C12 118.63(10) . . ?
N2 C1 C2 122.63(10) . . ?
N2 C1 C15 115.01(10) . . ?
C2 C1 C15 122.23(10) . . ?
C3 C2 C1 169.99(12) . . ?
C2 C3 Si1 171.87(11) . . ?
Si1 C4 H4A 109.5 . . ?
Si1 C4 H4B 109.5 . . ?
Si1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
Si1 C5 H5A 109.5 . . ?
Si1 C5 H5B 109.5 . . ?
Si1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
Si1 C6 H6A 109.5 . . ?
Si1 C6 H6B 109.5 . . ?
Si1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O1 C7 H7A 109.6 . . ?
O1 C7 H7B 109.6 . . ?
O1 C7 C8 110.43(10) . . ?
H7A C7 H7B 108.1 . . ?
C8 C7 H7A 109.6 . . ?
C8 C7 H7B 109.6 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 C10 117.57(10) . . ?
N1 C9 C14 121.82(10) . . ?
C14 C9 C10 120.55(10) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.05(10) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 120.7 . . ?
C10 C11 C12 118.64(10) . . ?
C12 C11 H11 120.7 . . ?
C11 C12 N3 119.32(10) . . ?
C11 C12 C13 122.04(11) . . ?
C13 C12 N3 118.57(10) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 C12 119.21(10) . . ?
C14 C13 H13 120.4 . . ?
C9 C14 H14 120.3 . . ?
C13 C14 C9 119.49(10) . . ?
C13 C14 H14 120.3 . . ?
O1 C15 C1 110.53(9) . . ?
O2 C15 O1 125.19(10) . . ?
O2 C15 C1 124.28(10) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O4 0.868(16) 2.355(16) 3.0219(13) 133.8(13) 2_656 yes

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
O3 N3 C12 C11 -179.83(10) . . . . ?
O3 N3 C12 C13 3.13(15) . . . . ?
O4 N3 C12 C11 1.41(15) . . . . ?
O4 N3 C12 C13 -175.63(10) . . . . ?
N1 N2 C1 C2 -4.09(16) . . . . ?
N1 N2 C1 C15 179.82(9) . . . . ?
N1 C9 C10 C11 175.89(10) . . . . ?
N1 C9 C14 C13 -176.06(10) . . . . ?
N2 N1 C9 C10 -177.35(10) . . . . ?
N2 N1 C9 C14 -0.18(16) . . . . ?
N2 C1 C2 C3 -25.3(8) . . . . ?
N2 C1 C15 O1 -172.97(10) . . . . ?
N2 C1 C15 O2 6.91(17) . . . . ?
N3 C12 C13 C14 176.20(10) . . . . ?
C2 C1 C15 O1 10.92(15) . . . . ?
C2 C1 C15 O2 -169.20(11) . . . . ?
C7 O1 C15 O2 1.90(16) . . . . ?
C7 O1 C15 C1 -178.22(9) . . . . ?
C9 N1 N2 C1 173.03(10) . . . . ?
C9 C10 C11 C12 0.57(17) . . . . ?
C10 C9 C14 C13 1.03(17) . . . . ?
C10 C11 C12 N3 -176.47(10) . . . . ?
C10 C11 C12 C13 0.46(17) . . . . ?
C11 C12 C13 C14 -0.75(17) . . . . ?
C12 C13 C14 C9 -0.01(17) . . . . ?
C14 C9 C10 C11 -1.33(17) . . . . ?
C15 O1 C7 C8 88.72(12) . . . . ?
C15 C1 C2 C3 150.5(7) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id 'DS-Si  alk no-1'
_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 1.829
_oxdiff_exptl_absorpt_empirical_full_min 0.737
####################################################################### 
# 
# 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_ia923b
_database_code_depnum_ccdc_archive 'CCDC 2421979'
loop_
_audit_author_name
_audit_author_address
'Richard J Staples'
;Dartmouth College
United States of America
;
_audit_update_record             
;
2025-02-06 deposited with the CCDC.	2025-06-05 downloaded from the CCDC.
;
_audit_creation_date             2023-09-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H20 N4 O4'
_chemical_formula_sum            'C20 H20 N4 O4'
_chemical_formula_weight         380.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N4O4
_chemical_oxdiff_usercomment     DS-dma-no2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   12.63828(9)
_cell_length_b                   12.14363(11)
_cell_length_c                   24.6829(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.3855(8)
_cell_angle_gamma                90
_cell_volume                     3788.11(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    13108
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      78.7570
_cell_measurement_theta_min      3.5660
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.785
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.812
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.99a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1600
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 0 0.0988
1 0 0 0.0855
1 4 13 0.0533
0 -4 -13 0.0633
0 6 -9 0.0392
0 -7 9 0.0667

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.199
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.111
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0010 -0.0012 0.0018 -0.0051 -0.0408 -0.1148
1.0010 0.0012 -0.0018 0.0051 0.0408 0.1148
0.6891 4.2396 13.4427 -0.2114 -0.8843 0.4185
-0.2387 -4.2675 -13.4878 0.2161 0.9063 -0.3683
-0.3578 6.4757 -9.0989 -0.9688 0.2322 -0.0899
-0.0616 -6.5642 8.8654 0.9721 -0.2328 0.0356

_exptl_special_details           
;
Data was collected using a Rigaku Synergy S Diffractometer diffractometer equipped 
with an Oxford 800 low-temperature apparatus.  A suitable 
crystal was chosen and mounted on a nylon loop using Paratone oil.  Data  were 
measured based on the Pre-Experiment plugin of CrysAlisPro software.  Cell 
parameters were retrieved using CrysAlisPro software and data reduction was 
performed using the intergration software inside the CrysAlisPro which 
corrects for Lp.  The structure was solved by the direct method using the 
SHELXT program and refined by least squares method on F2, SHELXL,
 incorporated in OLEX2. 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            19891
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.387
_diffrn_reflns_theta_min         3.581
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    109.00 178.00   0.50    0.16    --  113.25 101.00 163.00  138
  2  ω     97.00 178.00   0.50    0.16    --  113.25 125.00-180.00  162
  3  ω    -27.00  39.00   0.50    0.05    --   47.11 -26.00-178.00  132
  4  ω    -27.00  38.00   0.50    0.05    --   47.11 -19.00 -60.00  130
  5  ω    -26.00  46.00   0.50    0.05    --   47.11 -37.00  60.00  144
  6  ω     42.00 104.00   0.50    0.16    --  113.25 -94.00  30.00  124
  7  ω     44.00 108.00   0.50    0.16    --  113.25-125.00 120.00  128
  8  ω     56.00 134.00   0.50    0.16    --  113.25-163.00-174.00  156
  9  ω     42.00 104.00   0.50    0.16    --  113.25 -94.00-120.00  124
 10  ω     42.00  69.00   0.50    0.16    --  113.25 -61.00-150.00   54
 11  ω     42.00  94.00   0.50    0.16    --  113.25 -77.00 -30.00  104
 12  ω     42.00  69.00   0.50    0.16    --  113.25 -61.00  30.00   54
 13  ω     42.00  94.00   0.50    0.16    --  113.25 -77.00  90.00  104
 14  ω     42.00  94.00   0.50    0.16    --  113.25 -77.00 120.00  104
 15  ω     42.00  69.00   0.50    0.16    --  113.25 -61.00 150.00   54
 16  ω     42.00  69.00   0.50    0.16    --  113.25 -61.00 -30.00   54
 17  ω     42.00  69.00   0.50    0.16    --  113.25 -61.00 -90.00   54
 18  ω    101.00 178.00   0.50    0.16    --  113.25  26.00 -15.00  154
 19  ω    106.00 178.00   0.50    0.16    --  113.25  61.00 -60.00  144
 20  ω    110.00 178.00   0.50    0.16    --  113.25  77.00   0.00  136
 21  ω    110.00 178.00   0.50    0.16    --  113.25  77.00  90.00  136
 22  ω     35.00  70.00   0.50    0.05    --   47.11  37.00 120.00   70
 23  ω     35.00 120.00   0.50    0.05    --   47.11  37.00-120.00  170
 24  ω    -53.00 -20.00   0.50    0.16    --  -91.75  45.00 -60.00   66
 25  ω    -70.00  16.00   0.50    0.05    --  -47.11  77.00 -90.00  172
 26  ω   -109.00 -34.00   0.50    0.16    --  -91.75 163.00-148.00  150
 27  ω    -78.00 -21.00   0.50    0.16    --  -91.75 101.00 163.00  114
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0052323000
_diffrn_orient_matrix_UB_12      -0.1190371000
_diffrn_orient_matrix_UB_13      0.0215455000
_diffrn_orient_matrix_UB_21      0.0407292000
_diffrn_orient_matrix_UB_22      -0.0396771000
_diffrn_orient_matrix_UB_23      -0.0553595000
_diffrn_orient_matrix_UB_31      0.1146765000
_diffrn_orient_matrix_UB_32      0.0193582000
_diffrn_orient_matrix_UB_33      0.0191502000
_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_current           1
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3680
_reflns_number_total             4006
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.00024(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         4006
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0345
_refine_ls_restrained_S_all      1.057
_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)+(0.0491P)²+2.0041P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.0959
_refine_special_details          
;
The structure was refined by Least Squares SHELXL incorporated 
in Olex2 software program. All non-hydrogen atoms were refined anisotropically. 
Hydrogen atom positions were calculated geometrically and refined using the 
riding model, except for the hydrogen atom on the non-carbon atom(s) which were found 
by difference Fourier methods and refined isotropically when data permits.
;
_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 Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C16(H16), C17(H17), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.76932(5) 0.69072(6) 0.34683(3) 0.02224(17) Uani 1 1 d . . . . .
O2 O 0.81062(6) 0.53450(6) 0.39145(3) 0.02283(17) Uani 1 1 d . . . . .
O3 O 0.09902(6) 0.95320(7) 0.27924(4) 0.0310(2) Uani 1 1 d . . . . .
O4 O 0.22975(7) 1.01584(7) 0.23259(4) 0.0330(2) Uani 1 1 d . . . . .
N1 N 0.46420(7) 0.64405(7) 0.36228(4) 0.02029(19) Uani 1 1 d . . . . .
H1 H 0.4376(11) 0.5890(13) 0.3789(6) 0.029(3) Uiso 1 1 d . . . . .
N2 N 0.56852(6) 0.65535(7) 0.35644(4) 0.01955(19) Uani 1 1 d . . . . .
N3 N 0.45028(8) 0.06563(8) 0.57441(4) 0.0299(2) Uani 1 1 d . . . . .
N4 N 0.19287(7) 0.95247(7) 0.26614(4) 0.02199(19) Uani 1 1 d . . . . .
C1 C 0.62967(8) 0.58169(8) 0.37853(4) 0.0193(2) Uani 1 1 d . . . . .
C2 C 0.59508(8) 0.48899(9) 0.40870(4) 0.0212(2) Uani 1 1 d . . . . .
C3 C 0.56410(8) 0.41351(9) 0.43600(4) 0.0226(2) Uani 1 1 d . . . . .
C4 C 0.53296(8) 0.32345(9) 0.46947(4) 0.0222(2) Uani 1 1 d . . . . .
C5 C 0.60714(8) 0.24336(10) 0.48489(5) 0.0260(2) Uani 1 1 d . . . . .
H5 H 0.677122 0.247622 0.471236 0.031 Uiso 1 1 calc R U . . .
C6 C 0.58087(9) 0.15860(9) 0.51939(5) 0.0264(2) Uani 1 1 d . . . . .
H6 H 0.633129 0.106164 0.529570 0.032 Uiso 1 1 calc R U . . .
C7 C 0.47700(9) 0.14875(9) 0.53983(4) 0.0234(2) Uani 1 1 d . . . . .
C8 C 0.40185(8) 0.22803(9) 0.52294(4) 0.0227(2) Uani 1 1 d . . . . .
H8 H 0.330945 0.222348 0.535173 0.027 Uiso 1 1 calc R U . . .
C9 C 0.42945(8) 0.31354(9) 0.48903(4) 0.0223(2) Uani 1 1 d . . . . .
H9 H 0.377638 0.366404 0.478794 0.027 Uiso 1 1 calc R U . . .
C10 C 0.34152(10) 0.05290(11) 0.59160(5) 0.0352(3) Uani 1 1 d . . . . .
H10A H 0.321162 0.116212 0.613835 0.053 Uiso 1 1 calc R U . . .
H10B H 0.334713 -0.014800 0.612902 0.053 Uiso 1 1 calc R U . . .
H10C H 0.295158 0.048688 0.559682 0.053 Uiso 1 1 calc R U . . .
C11 C 0.52889(10) -0.01287(10) 0.59327(5) 0.0310(3) Uani 1 1 d . . . . .
H11A H 0.551728 -0.058859 0.562895 0.047 Uiso 1 1 calc R U . . .
H11B H 0.498080 -0.059583 0.621438 0.047 Uiso 1 1 calc R U . . .
H11C H 0.589957 0.026835 0.608227 0.047 Uiso 1 1 calc R U . . .
C12 C 0.74610(8) 0.59847(8) 0.37298(4) 0.0190(2) Uani 1 1 d . . . . .
C13 C 0.88025(8) 0.70860(9) 0.33425(5) 0.0237(2) Uani 1 1 d . . . . .
H13A H 0.911212 0.641989 0.317516 0.028 Uiso 1 1 calc R U . . .
H13B H 0.920913 0.726483 0.367522 0.028 Uiso 1 1 calc R U . . .
C14 C 0.88238(9) 0.80335(10) 0.29537(5) 0.0282(2) Uani 1 1 d . . . . .
H14A H 0.842694 0.783850 0.262500 0.042 Uiso 1 1 calc R U . . .
H14B H 0.955820 0.820134 0.285913 0.042 Uiso 1 1 calc R U . . .
H14C H 0.850021 0.868020 0.312273 0.042 Uiso 1 1 calc R U . . .
C15 C 0.39830(8) 0.72207(8) 0.33882(4) 0.0187(2) Uani 1 1 d . . . . .
C16 C 0.43929(8) 0.80651(8) 0.30635(4) 0.0206(2) Uani 1 1 d . . . . .
H16 H 0.513418 0.811995 0.300838 0.025 Uiso 1 1 calc R U . . .
C17 C 0.37153(8) 0.88165(8) 0.28243(4) 0.0210(2) Uani 1 1 d . . . . .
H17 H 0.398430 0.938393 0.259889 0.025 Uiso 1 1 calc R U . . .
C18 C 0.26346(8) 0.87321(8) 0.29175(4) 0.0194(2) Uani 1 1 d . . . . .
C19 C 0.22163(8) 0.79120(8) 0.32460(4) 0.0205(2) Uani 1 1 d . . . . .
H19 H 0.147614 0.787477 0.330795 0.025 Uiso 1 1 calc R U . . .
C20 C 0.28915(8) 0.71520(8) 0.34811(4) 0.0208(2) Uani 1 1 d . . . . .
H20 H 0.261708 0.658489 0.370501 0.025 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C12 1.3267(13) . ?
O1 C13 1.4543(12) . ?
O2 C12 1.2130(12) . ?
O3 N4 1.2315(12) . ?
O4 N4 1.2250(12) . ?
N1 H1 0.855(16) . ?
N1 N2 1.3343(12) . ?
N1 C15 1.3857(13) . ?
N2 C1 1.2996(13) . ?
N3 C7 1.3658(14) . ?
N3 C10 1.4495(15) . ?
N3 C11 1.4513(15) . ?
N4 C18 1.4541(13) . ?
C1 C2 1.4202(14) . ?
C1 C12 1.4927(13) . ?
C2 C3 1.2046(16) . ?
C3 C4 1.4276(15) . ?
C4 C5 1.4017(15) . ?
C4 C9 1.4026(15) . ?
C5 H5 0.9500 . ?
C5 C6 1.3780(16) . ?
C6 H6 0.9500 . ?
C6 C7 1.4146(15) . ?
C7 C8 1.4133(15) . ?
C8 H8 0.9500 . ?
C8 C9 1.3800(15) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.4986(16) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.4026(14) . ?
C15 C20 1.4024(13) . ?
C16 H16 0.9500 . ?
C16 C17 1.3813(14) . ?
C17 H17 0.9500 . ?
C17 C18 1.3903(14) . ?
C18 C19 1.3909(15) . ?
C19 H19 0.9500 . ?
C19 C20 1.3820(14) . ?
C20 H20 0.9500 . ?

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
C12 O1 C13 116.53(8) . . ?
N2 N1 H1 121.6(10) . . ?
N2 N1 C15 118.44(9) . . ?
C15 N1 H1 119.9(10) . . ?
C1 N2 N1 117.99(9) . . ?
C7 N3 C10 120.04(10) . . ?
C7 N3 C11 120.95(10) . . ?
C10 N3 C11 118.98(10) . . ?
O3 N4 C18 118.67(9) . . ?
O4 N4 O3 123.00(9) . . ?
O4 N4 C18 118.33(9) . . ?
N2 C1 C2 125.53(9) . . ?
N2 C1 C12 116.83(9) . . ?
C2 C1 C12 117.61(9) . . ?
C3 C2 C1 177.11(11) . . ?
C2 C3 C4 176.96(11) . . ?
C5 C4 C3 120.14(10) . . ?
C5 C4 C9 118.08(10) . . ?
C9 C4 C3 121.76(9) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 C4 121.50(10) . . ?
C6 C5 H5 119.2 . . ?
C5 C6 H6 119.6 . . ?
C5 C6 C7 120.77(10) . . ?
C7 C6 H6 119.6 . . ?
N3 C7 C6 121.28(10) . . ?
N3 C7 C8 121.29(10) . . ?
C8 C7 C6 117.43(10) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 C7 121.29(10) . . ?
C9 C8 H8 119.4 . . ?
C4 C9 H9 119.6 . . ?
C8 C9 C4 120.89(10) . . ?
C8 C9 H9 119.6 . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N3 C11 H11A 109.5 . . ?
N3 C11 H11B 109.5 . . ?
N3 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O1 C12 C1 112.42(8) . . ?
O2 C12 O1 124.97(9) . . ?
O2 C12 C1 122.59(9) . . ?
O1 C13 H13A 110.6 . . ?
O1 C13 H13B 110.6 . . ?
O1 C13 C14 105.83(8) . . ?
H13A C13 H13B 108.7 . . ?
C14 C13 H13A 110.6 . . ?
C14 C13 H13B 110.6 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 C16 121.02(9) . . ?
N1 C15 C20 118.69(9) . . ?
C20 C15 C16 120.29(9) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.79(9) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 120.4 . . ?
C16 C17 C18 119.17(9) . . ?
C18 C17 H17 120.4 . . ?
C17 C18 N4 118.68(9) . . ?
C17 C18 C19 121.79(9) . . ?
C19 C18 N4 119.53(9) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 C18 119.14(9) . . ?
C20 C19 H19 120.4 . . ?
C15 C20 H20 120.1 . . ?
C19 C20 C15 119.78(9) . . ?
C19 C20 H20 120.1 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O2 0.855(16) 2.220(16) 3.0010(11) 151.9(13) 6_565 yes

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
O3 N4 C18 C17 -171.65(9) . . . . ?
O3 N4 C18 C19 8.52(14) . . . . ?
O4 N4 C18 C17 8.10(14) . . . . ?
O4 N4 C18 C19 -171.73(9) . . . . ?
N1 N2 C1 C2 0.03(15) . . . . ?
N1 N2 C1 C12 -177.97(8) . . . . ?
N1 C15 C16 C17 178.47(9) . . . . ?
N1 C15 C20 C19 -179.17(9) . . . . ?
N2 N1 C15 C16 4.62(14) . . . . ?
N2 N1 C15 C20 -175.40(9) . . . . ?
N2 C1 C12 O1 1.88(13) . . . . ?
N2 C1 C12 O2 -179.22(9) . . . . ?
N3 C7 C8 C9 178.43(10) . . . . ?
N4 C18 C19 C20 179.03(9) . . . . ?
C2 C1 C12 O1 -176.28(9) . . . . ?
C2 C1 C12 O2 2.62(15) . . . . ?
C3 C4 C5 C6 176.64(10) . . . . ?
C3 C4 C9 C8 -177.63(10) . . . . ?
C4 C5 C6 C7 0.98(18) . . . . ?
C5 C4 C9 C8 0.69(16) . . . . ?
C5 C6 C7 N3 -179.43(11) . . . . ?
C5 C6 C7 C8 0.76(16) . . . . ?
C6 C7 C8 C9 -1.77(16) . . . . ?
C7 C8 C9 C4 1.06(16) . . . . ?
C9 C4 C5 C6 -1.71(16) . . . . ?
C10 N3 C7 C6 -175.53(11) . . . . ?
C10 N3 C7 C8 4.26(17) . . . . ?
C11 N3 C7 C6 2.70(17) . . . . ?
C11 N3 C7 C8 -177.51(10) . . . . ?
C12 O1 C13 C14 168.31(9) . . . . ?
C13 O1 C12 O2 7.51(15) . . . . ?
C13 O1 C12 C1 -173.62(8) . . . . ?
C15 N1 N2 C1 -179.91(9) . . . . ?
C15 C16 C17 C18 1.04(15) . . . . ?
C16 C15 C20 C19 0.82(15) . . . . ?
C16 C17 C18 N4 -179.72(9) . . . . ?
C16 C17 C18 C19 0.10(15) . . . . ?
C17 C18 C19 C20 -0.80(15) . . . . ?
C18 C19 C20 C15 0.32(15) . . . . ?
C20 C15 C16 C17 -1.51(15) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id 'DS-dma no2'
_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 1.223
_oxdiff_exptl_absorpt_empirical_full_min 0.880
