# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_kwj-2022-346
_audit_block_doi                 10.5517/ccdc.csd.cc2gw3gy
_database_code_depnum_ccdc_archive 'CCDC 2290170'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2023-vt063 2023
loop_
_audit_author_name
_audit_author_address
'Nathan D. Schley'
;Vanderbilt University
United States of America
;
_audit_update_record             
;
2023-08-22 deposited with the CCDC.	2023-10-10 downloaded from the CCDC.
;
_audit_creation_date             2023-02-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H19 N O3'
_chemical_formula_sum            'C17 H19 N O3'
_chemical_formula_weight         285.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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                   5.4793(2)
_cell_length_b                   11.0980(4)
_cell_length_c                   12.6043(4)
_cell_angle_alpha                113.894(3)
_cell_angle_beta                 94.988(3)
_cell_angle_gamma                92.070(3)
_cell_volume                     695.97(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5545
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      71.5090
_cell_measurement_theta_min      3.8390
_shelx_estimated_absorpt_T_max   0.942
_shelx_estimated_absorpt_T_min   0.834
_exptl_absorpt_coefficient_mu    0.755
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.630
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.71a (Rigaku Oxford Diffraction, 2022)
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             304
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 6 1 0.0418
0 -6 -1 0.0418
0 6 -6 0.0625
0 -6 6 0.0625
0 -2 8 0.0746
0 2 -8 0.0876
-3 3 -3 0.0737
3 -3 3 0.0737

_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
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
-0.1239 6.0105 1.3369 0.8974 -0.2143 0.3856
0.1239 -6.0105 -1.3369 -0.8974 0.2143 -0.3856
0.0021 6.3210 -6.4925 0.7835 -0.0208 -0.6210
-0.0021 -6.3210 6.4925 -0.7835 0.0208 0.6210
0.0067 -2.0060 7.9959 -0.1322 -0.1770 0.9656
-0.0067 2.0060 -7.9959 0.1322 0.1770 -0.9656
-3.0035 2.9985 -2.9959 0.4844 0.8267 -0.2006
3.0035 -2.9985 2.9959 -0.4844 -0.8267 0.2006

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7678
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.757
_diffrn_reflns_theta_min         3.860
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1506
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -105.00 -17.00   1.00    1.00    --  -35.82 -38.00  90.00   88
  2  ω   -105.00 -17.00   1.00    1.00    --  -35.82 -38.00  60.00   88
  3  ω   -105.00 -17.00   1.00    1.00    --  -35.82 -38.00 -30.00   88
  4  ω   -108.00 -37.00   1.00    1.00    --  -35.82 178.00-150.00   71
  5  ω    -21.00  63.00   1.00    1.00    --   35.82 -77.00-150.00   84
  6  ω      6.00  74.00   1.00    1.00    --   35.82 -99.00  90.00   68
  7  ω     61.00 108.00   1.00    1.00    --   35.82 178.00   0.00   47
  8  ω      6.00  74.00   1.00    1.00    --   35.82 -99.00  60.00   68
  9  ω      6.00  74.00   1.00    1.00    --   35.82 -99.00-180.00   68
 10  ω      6.00  74.00   1.00    1.00    --   35.82 -99.00 -60.00   68
 11  ω    103.00 176.00   1.00    1.00    --  108.40  77.00 -30.00   73
 12  ω     37.00 147.00   1.00    1.00    --  108.40 -15.00-120.00  110
 13  ω     42.00 126.00   1.00    1.00    --  108.40 -61.00 -90.00   84
 14  ω     41.00 109.00   1.00    1.00    --  108.40-111.00 -30.00   68
 15  ω    103.00 176.00   1.00    1.00    --  108.40  77.00 -90.00   73
 16  ω     41.00 135.00   1.00    1.00    --  108.40 -77.00  30.00   94
 17  ω     38.00 130.00   1.00    1.00    --  108.40 -30.00 -60.00   92
 18  ω     39.00 107.00   1.00    1.00    --  108.40 -94.00-120.00   68
 19  ω     39.00 107.00   1.00    1.00    --  108.40 -94.00 -30.00   68
 20  ω     38.00 130.00   1.00    1.00    --  108.40 -30.00  30.00   92
 21  ω     41.00 109.00   1.00    1.00    --  108.40-111.00 120.00   68
 22  ω     40.00 126.00   1.00    1.00    --  108.40 -45.00-180.00   86
 23  ω     91.00 177.00   1.00    1.00    --  108.40  45.00 -30.00   86
 24  ω     91.00 177.00   1.00    1.00    --  108.40  45.00-120.00   86
 25  ω     41.00 109.00   1.00    1.00    --  108.40-111.00-150.00   68
 26  ω   -103.00 -19.00   1.00    1.00    --  -35.82 -57.00-150.00   84
 27  ω    -65.00  36.00   1.00    1.00    --  -35.82  19.00  90.00  101
 28  ω   -103.00 -19.00   1.00    1.00    --  -35.82 -57.00 -90.00   84
 29  ω   -103.00 -19.00   1.00    1.00    --  -35.82 -57.00 150.00   84
 30  ω   -103.00 -19.00   1.00    1.00    --  -35.82 -57.00 -30.00   84
 31  ω     19.00  93.00   1.00    1.00    --   35.82  57.00  90.00   74
 32  ω    -31.00  -3.00   1.00    1.00    --   35.82 -57.00 120.00   28
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0369684000
_diffrn_orient_matrix_UB_12      0.1441723000
_diffrn_orient_matrix_UB_13      0.0196735000
_diffrn_orient_matrix_UB_21      -0.2793080000
_diffrn_orient_matrix_UB_22      -0.0346148000
_diffrn_orient_matrix_UB_23      -0.0305862000
_diffrn_orient_matrix_UB_31      -0.0276628000
_diffrn_orient_matrix_UB_32      0.0347807000
_diffrn_orient_matrix_UB_33      0.1295067000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2501
_reflns_number_total             2683
_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 1.171.42.71a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.71a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.71a (Rigaku OD, 2022)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2683
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0353
_refine_ls_restrained_S_all      1.026
_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)+(0.0472P)²+0.2816P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0920
_refine_special_details          'Refined without additional restraints'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B),
 C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.42036(15) 0.55767(8) 0.37277(7) 0.0191(2) Uani 1 1 d . . . . .
O2 O 0.46911(15) 0.88948(8) 0.35703(7) 0.01680(19) Uani 1 1 d . . . . .
O3 O -0.06393(16) 0.79753(9) 0.68801(7) 0.0225(2) Uani 1 1 d . . . . .
N1 N 0.22384(17) 0.72275(9) 0.49977(8) 0.0150(2) Uani 1 1 d . . . . .
C1 C 0.2895(2) 0.65089(11) 0.39293(10) 0.0134(2) Uani 1 1 d . . . . .
C2 C 0.1986(2) 0.68629(11) 0.29362(10) 0.0136(2) Uani 1 1 d . . . . .
C3 C 0.3159(2) 0.80891(11) 0.28750(9) 0.0128(2) Uani 1 1 d . . . . .
C4 C 0.1927(2) 0.80391(11) 0.17050(10) 0.0154(2) Uani 1 1 d . . . . .
H4 H 0.085528 0.879000 0.186430 0.019 Uiso 1 1 calc R U . . .
C5 C 0.0310(2) 0.67453(12) 0.13545(10) 0.0176(3) Uani 1 1 d . . . . .
H5 H -0.078644 0.638046 0.060012 0.021 Uiso 1 1 calc R U . . .
C6 C -0.0759(2) 0.69543(12) 0.25065(10) 0.0189(3) Uani 1 1 d . . . . .
H6A H -0.191981 0.622368 0.245660 0.023 Uiso 1 1 calc R U . . .
H6B H -0.140575 0.782817 0.290682 0.023 Uiso 1 1 calc R U . . .
C7 C 0.2118(2) 0.58515(11) 0.16506(10) 0.0166(2) Uani 1 1 d . . . . .
H7A H 0.374743 0.584953 0.136641 0.020 Uiso 1 1 calc R U . . .
H7B H 0.141797 0.494505 0.146537 0.020 Uiso 1 1 calc R U . . .
C8 C 0.3753(2) 0.80920(11) 0.08867(10) 0.0154(2) Uani 1 1 d . . . . .
C9 C 0.5476(2) 0.91748(11) 0.12397(10) 0.0180(3) Uani 1 1 d . . . . .
H9 H 0.551141 0.986439 0.199789 0.022 Uiso 1 1 calc R U . . .
C10 C 0.7140(2) 0.92577(12) 0.04973(11) 0.0213(3) Uani 1 1 d . . . . .
H10 H 0.831162 0.999778 0.075210 0.026 Uiso 1 1 calc R U . . .
C11 C 0.7096(2) 0.82621(13) -0.06169(11) 0.0213(3) Uani 1 1 d . . . . .
H11 H 0.823255 0.831976 -0.112542 0.026 Uiso 1 1 calc R U . . .
C12 C 0.5386(2) 0.71849(12) -0.09820(10) 0.0209(3) Uani 1 1 d . . . . .
H12 H 0.534082 0.650478 -0.174549 0.025 Uiso 1 1 calc R U . . .
C13 C 0.3732(2) 0.70956(12) -0.02328(10) 0.0188(3) Uani 1 1 d . . . . .
H13 H 0.257776 0.634810 -0.048708 0.023 Uiso 1 1 calc R U . . .
C14 C 0.2886(2) 0.68705(12) 0.59819(10) 0.0175(2) Uani 1 1 d . . . . .
H14A H 0.409881 0.754916 0.656547 0.021 Uiso 1 1 calc R U . . .
H14B H 0.362941 0.601146 0.570374 0.021 Uiso 1 1 calc R U . . .
C15 C 0.0573(2) 0.67763(12) 0.65349(11) 0.0206(3) Uani 1 1 d . . . . .
H15A H -0.056097 0.603632 0.596977 0.025 Uiso 1 1 calc R U . . .
H15B H 0.100829 0.658543 0.722711 0.025 Uiso 1 1 calc R U . . .
C16 C -0.1343(2) 0.82397(12) 0.58822(10) 0.0190(3) Uani 1 1 d . . . . .
H16A H -0.224421 0.904916 0.611963 0.023 Uiso 1 1 calc R U . . .
H16B H -0.245489 0.749554 0.530730 0.023 Uiso 1 1 calc R U . . .
C17 C 0.0904(2) 0.84231(11) 0.53251(10) 0.0163(2) Uani 1 1 d . . . . .
H17A H 0.039724 0.858505 0.462389 0.020 Uiso 1 1 calc R U . . .
H17B H 0.197978 0.919577 0.588276 0.020 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2335(14) . ?
O2 C3 1.2062(14) . ?
O3 C15 1.4305(15) . ?
O3 C16 1.4282(15) . ?
N1 C1 1.3468(15) . ?
N1 C14 1.4674(14) . ?
N1 C17 1.4645(14) . ?
C1 C2 1.5078(15) . ?
C2 C3 1.5171(15) . ?
C2 C6 1.5748(15) . ?
C2 C7 1.5633(15) . ?
C3 C4 1.5465(15) . ?
C4 H4 1.0000 . ?
C4 C5 1.5390(16) . ?
C4 C8 1.5140(15) . ?
C5 H5 1.0000 . ?
C5 C6 1.5460(16) . ?
C5 C7 1.5531(16) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.3947(16) . ?
C8 C13 1.3951(16) . ?
C9 H9 0.9500 . ?
C9 C10 1.3883(17) . ?
C10 H10 0.9500 . ?
C10 C11 1.3888(18) . ?
C11 H11 0.9500 . ?
C11 C12 1.3846(18) . ?
C12 H12 0.9500 . ?
C12 C13 1.3932(17) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.5185(16) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.5162(16) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?

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
C16 O3 C15 109.84(9) . . ?
C1 N1 C14 121.22(9) . . ?
C1 N1 C17 125.90(9) . . ?
C17 N1 C14 112.86(9) . . ?
O1 C1 N1 123.00(10) . . ?
O1 C1 C2 118.64(10) . . ?
N1 C1 C2 118.36(9) . . ?
C1 C2 C3 118.60(9) . . ?
C1 C2 C6 127.35(9) . . ?
C1 C2 C7 119.38(9) . . ?
C3 C2 C6 99.49(9) . . ?
C3 C2 C7 99.32(9) . . ?
C7 C2 C6 85.22(8) . . ?
O2 C3 C2 128.07(10) . . ?
O2 C3 C4 128.94(10) . . ?
C2 C3 C4 103.00(9) . . ?
C3 C4 H4 109.3 . . ?
C5 C4 C3 96.89(9) . . ?
C5 C4 H4 109.3 . . ?
C8 C4 C3 113.28(9) . . ?
C8 C4 H4 109.3 . . ?
C8 C4 C5 117.94(9) . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 102.06(9) . . ?
C4 C5 C7 102.25(9) . . ?
C6 C5 H5 119.9 . . ?
C6 C5 C7 86.56(9) . . ?
C7 C5 H5 119.9 . . ?
C2 C6 H6A 114.8 . . ?
C2 C6 H6B 114.8 . . ?
C5 C6 C2 83.24(8) . . ?
C5 C6 H6A 114.8 . . ?
C5 C6 H6B 114.8 . . ?
H6A C6 H6B 111.8 . . ?
C2 C7 H7A 114.7 . . ?
C2 C7 H7B 114.7 . . ?
C5 C7 C2 83.39(8) . . ?
C5 C7 H7A 114.7 . . ?
C5 C7 H7B 114.7 . . ?
H7A C7 H7B 111.8 . . ?
C9 C8 C4 119.75(10) . . ?
C9 C8 C13 118.44(11) . . ?
C13 C8 C4 121.78(10) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.84(11) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.21(11) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.60(11) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.19(11) . . ?
C13 C12 H12 119.9 . . ?
C8 C13 H13 119.6 . . ?
C12 C13 C8 120.72(11) . . ?
C12 C13 H13 119.6 . . ?
N1 C14 H14A 109.9 . . ?
N1 C14 H14B 109.9 . . ?
N1 C14 C15 108.84(9) . . ?
H14A C14 H14B 108.3 . . ?
C15 C14 H14A 109.9 . . ?
C15 C14 H14B 109.9 . . ?
O3 C15 C14 111.47(9) . . ?
O3 C15 H15A 109.3 . . ?
O3 C15 H15B 109.3 . . ?
C14 C15 H15A 109.3 . . ?
C14 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
O3 C16 H16A 109.6 . . ?
O3 C16 H16B 109.6 . . ?
O3 C16 C17 110.43(10) . . ?
H16A C16 H16B 108.1 . . ?
C17 C16 H16A 109.6 . . ?
C17 C16 H16B 109.6 . . ?
N1 C17 C16 108.90(9) . . ?
N1 C17 H17A 109.9 . . ?
N1 C17 H17B 109.9 . . ?
C16 C17 H17A 109.9 . . ?
C16 C17 H17B 109.9 . . ?
H17A C17 H17B 108.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -105.37(12) . . . . ?
O1 C1 C2 C6 123.90(12) . . . . ?
O1 C1 C2 C7 15.88(15) . . . . ?
O2 C3 C4 C5 178.86(11) . . . . ?
O2 C3 C4 C8 54.41(15) . . . . ?
O3 C16 C17 N1 58.24(12) . . . . ?
N1 C1 C2 C3 74.61(13) . . . . ?
N1 C1 C2 C6 -56.12(15) . . . . ?
N1 C1 C2 C7 -164.14(10) . . . . ?
N1 C14 C15 O3 -55.84(12) . . . . ?
C1 N1 C14 C15 -127.43(11) . . . . ?
C1 N1 C17 C16 126.08(11) . . . . ?
C1 C2 C3 O2 -4.51(17) . . . . ?
C1 C2 C3 C4 175.02(9) . . . . ?
C1 C2 C6 C5 -157.73(11) . . . . ?
C1 C2 C7 C5 164.46(10) . . . . ?
C2 C3 C4 C5 -0.65(10) . . . . ?
C2 C3 C4 C8 -125.11(10) . . . . ?
C3 C2 C6 C5 64.69(9) . . . . ?
C3 C2 C7 C5 -65.06(9) . . . . ?
C3 C4 C5 C6 45.30(10) . . . . ?
C3 C4 C5 C7 -43.76(10) . . . . ?
C3 C4 C8 C9 -59.34(14) . . . . ?
C3 C4 C8 C13 122.18(11) . . . . ?
C4 C5 C6 C2 -67.62(9) . . . . ?
C4 C5 C7 C2 67.15(9) . . . . ?
C4 C8 C9 C10 -178.81(10) . . . . ?
C4 C8 C13 C12 178.15(10) . . . . ?
C5 C4 C8 C9 -171.43(10) . . . . ?
C5 C4 C8 C13 10.09(16) . . . . ?
C6 C2 C3 O2 137.85(12) . . . . ?
C6 C2 C3 C4 -42.63(10) . . . . ?
C6 C2 C7 C5 33.80(8) . . . . ?
C6 C5 C7 C2 -34.45(8) . . . . ?
C7 C2 C3 O2 -135.48(12) . . . . ?
C7 C2 C3 C4 44.04(10) . . . . ?
C7 C2 C6 C5 -33.99(8) . . . . ?
C7 C5 C6 C2 34.18(8) . . . . ?
C8 C4 C5 C6 166.28(10) . . . . ?
C8 C4 C5 C7 77.22(11) . . . . ?
C8 C9 C10 C11 0.52(18) . . . . ?
C9 C8 C13 C12 -0.34(17) . . . . ?
C9 C10 C11 C12 -0.12(18) . . . . ?
C10 C11 C12 C13 -0.50(18) . . . . ?
C11 C12 C13 C8 0.74(18) . . . . ?
C13 C8 C9 C10 -0.28(17) . . . . ?
C14 N1 C1 O1 -5.13(17) . . . . ?
C14 N1 C1 C2 174.90(9) . . . . ?
C14 N1 C17 C16 -55.23(12) . . . . ?
C15 O3 C16 C17 -61.64(12) . . . . ?
C16 O3 C15 C14 60.77(12) . . . . ?
C17 N1 C1 O1 173.46(10) . . . . ?
C17 N1 C1 C2 -6.52(16) . . . . ?
C17 N1 C14 C15 53.81(12) . . . . ?

_olex2_date_sample_data_collection 2023-02-15
_olex2_exptl_crystal_mounting_method 'mounted in a polyimide loop'
_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 1.333
_oxdiff_exptl_absorpt_empirical_full_min 0.821
####################################################################### 
# 
# 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_kwj-2023-413a
_audit_block_doi                 10.5517/ccdc.csd.cc2gw3hz
_database_code_depnum_ccdc_archive 'CCDC 2290171'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2023-vt063 2023
loop_
_audit_author_name
_audit_author_address
'Nathan D. Schley'
;Vanderbilt University
United States of America
;
_audit_update_record             
;
2023-08-22 deposited with the CCDC.	2023-10-10 downloaded from the CCDC.
;
_audit_creation_date             2023-02-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H22 N2 O4'
_chemical_formula_sum            'C19 H22 N2 O4'
_chemical_formula_weight         342.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H24N2O3
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                   6.8191(4)
_cell_length_b                   10.9500(8)
_cell_length_c                   12.1182(10)
_cell_angle_alpha                85.949(6)
_cell_angle_beta                 78.293(6)
_cell_angle_gamma                80.362(6)
_cell_volume                     872.90(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3745
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      71.4710
_cell_measurement_theta_min      3.7000
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.889
_exptl_absorpt_coefficient_mu    0.753
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.882
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.71a (Rigaku Oxford Diffraction, 2022)
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             364
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 7 -2 0.0445
4 0 0 0.0585
-4 0 0 0.0731
-1 -7 -2 0.0495
0 -1 -8 0.0186
0 1 8 0.0116

_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_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
-0.5067 6.5827 -1.9026 0.5582 -0.8114 -0.1733
4.3068 0.3852 -0.0402 0.0062 -0.0067 1.0000
-4.3004 -0.2167 -0.0082 0.0080 -0.0139 -0.9999
-1.0681 -6.9562 -2.1248 -0.8997 0.4286 -0.0829
-0.0730 -1.4180 -7.6258 -0.7440 -0.6359 0.2050
0.0730 1.4180 7.6258 0.7440 0.6359 -0.2050

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9350
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.782
_diffrn_reflns_theta_min         3.728
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1506
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -105.00 -17.00   1.00    3.00    --  -36.07 -38.00 120.00   88
  2  ω    -63.00  31.00   1.00    3.00    --  -36.07  77.00  60.00   94
  3  ω    -53.00  31.00   1.00    3.00    --  -36.07  57.00  60.00   84
  4  ω    -55.00  33.00   1.00    3.00    --  -36.07  38.00   0.00   88
  5  ω   -103.00 -19.00   1.00    3.00    --  -36.07 -57.00-150.00   84
  6  ω    -63.00  31.00   1.00    3.00    --  -36.07  77.00 -60.00   94
  7  ω    -21.00  63.00   1.00    3.00    --   36.07 -77.00-150.00   84
  8  ω    -21.00  63.00   1.00    3.00    --   36.07 -77.00 120.00   84
  9  ω      5.00  33.00   1.00    3.00    --   36.07  84.00  -1.78   28
 10  ω      4.00  31.00   1.00    3.00    --   36.07  86.00 118.78   27
 11  ω    -33.00  55.00   1.00    3.00    --   36.07 -38.00  60.00   88
 12  ω     40.00 106.00   1.00   18.00    --  108.40 -89.00  26.17   66
 13  ω    103.00 176.00   1.00   18.00    --  108.40  77.00  90.00   73
 14  ω     41.00 135.00   1.00   18.00    --  108.40 -77.00  90.00   94
 15  ω     42.00 126.00   1.00   18.00    --  108.40 -61.00-180.00   84
 16  ω     39.00 106.00   1.00   18.00    --  108.40 -90.00 -15.95   67
 17  ω     38.00 130.00   1.00   18.00    --  108.40 -30.00 120.00   92
 18  ω     38.00 130.00   1.00   18.00    --  108.40 -30.00-180.00   92
 19  ω    103.00 176.00   1.00   18.00    --  108.40  77.00 150.00   73
 20  ω    103.00 176.00   1.00   18.00    --  108.40  77.00 120.00   73
 21  ω     91.00 177.00   1.00   18.00    --  108.40  45.00-180.00   86
 22  ω     40.00 126.00   1.00   18.00    --  108.40 -45.00  30.00   86
 23  ω     41.00 135.00   1.00   18.00    --  108.40 -77.00 -60.00   94
 24  ω     40.00 106.00   1.00   18.00    --  108.40 -89.00 -67.55   66
 25  ω     39.00 106.00   1.00   18.00    --  108.40 -90.00-131.83   67
 26  ω     87.00 178.00   1.00   18.00    --  108.40  30.00  90.00   91
 27  ω     39.00 106.00   1.00   18.00    --  108.40 -90.00 140.61   67
 28  ω   -103.00 -19.00   1.00    3.00    --  -36.07 -57.00   0.00   84
 29  ω   -105.00 -17.00   1.00    3.00    --  -36.07 -38.00  60.00   88
 30  ω   -103.00 -19.00   1.00    3.00    --  -36.07 -57.00 -60.00   84
 31  ω    -65.00  35.00   1.00    3.00    --  -36.07  19.00 -90.00  100
 32  ω      2.00  29.00   1.00    3.00    --   36.07  90.00  61.51   27
 33  ω      3.00  30.00   1.00    3.00    --   36.07  89.00 154.86   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0073851000
_diffrn_orient_matrix_UB_12      0.1067095000
_diffrn_orient_matrix_UB_13      0.0777963000
_diffrn_orient_matrix_UB_21      0.0077457000
_diffrn_orient_matrix_UB_22      -0.0935601000
_diffrn_orient_matrix_UB_23      0.1007152000
_diffrn_orient_matrix_UB_31      0.2333587000
_diffrn_orient_matrix_UB_32      -0.0159232000
_diffrn_orient_matrix_UB_33      -0.0261516000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2644
_reflns_number_total             3346
_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 1.171.42.71a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.71a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.71a (Rigaku OD, 2022)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         3346
_refine_ls_number_restraints     91
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0722
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1357P)²+0.3239P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1978
_refine_ls_wR_factor_ref         0.2161
_refine_special_details          
'Conformational disorder in the morpholinyl group was modeled over two positions with similarity restraints placed on bond distances and atomic thermal parameters.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N2-C8 \\sim N2A-C8
 with sigma of 0.02
 C12-C11 \\sim C9A-C10A \\sim C9-C10 \\sim C12A-C11A
 with sigma of 0.02
 O4-C10 \\sim C11A-O4A \\sim C11-O4 \\sim O4A-C10A
 with sigma of 0.02
 N2A-C8 \\sim N2-C8
 with sigma of 0.02
 N2A-C12A \\sim N2-C9 \\sim N2-C12 \\sim N2A-C9A
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 O4A, N2A, C9A, C10A, C11A, C12A, O4, N2, C9, C10, C11, C12
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(O4A)=Sof(N2A)=Sof(C9A)=Sof(H9AA)=Sof(H9AB)=Sof(C10A)=Sof(H10C)=Sof(H10D)=
 Sof(C11A)=Sof(H11A)=Sof(H11B)=Sof(C12A)=Sof(H12C)=Sof(H12D)=1-FVAR(1)
 Sof(O4)=Sof(N2)=Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(C10)=Sof(H10A)=Sof(H10B)=
 Sof(C11)=Sof(H12A)=Sof(H12B)=Sof(C12)=Sof(H13A)=Sof(H13B)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C2(H2), C6(H6)
5.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C7(H7A,H7B), C9A(H9AA,H9AB), C10A(H10C,H10D), C11A(H11A,H11B),
 C12A(H12C,H12D), C9(H9A,H9B), C10(H10A,H10B), C11(H12A,H12B), C12(H13A,H13B)
5.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C17(H17), C18(H18)
5.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_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 0.6722(3) -0.01554(15) 0.61900(17) 0.0366(5) Uani 1 1 d . . . . .
O2 O 0.6406(3) 0.25709(17) 0.37527(17) 0.0392(5) Uani 1 1 d . . . . .
O3 O 0.2956(3) 0.56034(15) 0.35400(16) 0.0347(4) Uani 1 1 d . . . . .
N1 N 0.5875(3) 0.19341(18) 0.62662(19) 0.0295(5) Uani 1 1 d . . . . .
H1 H 0.620(5) 0.259(3) 0.648(2) 0.033(7) Uiso 1 1 d . . . . .
C1 C 0.6957(3) 0.0831(2) 0.6515(2) 0.0289(5) Uani 1 1 d . . . . .
C2 C 0.4348(3) 0.1994(2) 0.5584(2) 0.0283(5) Uani 1 1 d . . . . .
H2 H 0.413591 0.113533 0.546358 0.034 Uiso 1 1 calc R U . . .
C3 C 0.4851(3) 0.2682(2) 0.4435(2) 0.0296(5) Uani 1 1 d . . . . .
C4 C 0.2917(3) 0.3613(2) 0.4423(2) 0.0279(5) Uani 1 1 d . . . . .
C5 C 0.1259(3) 0.2797(2) 0.4997(2) 0.0300(5) Uani 1 1 d . . . . .
H5A H -0.015472 0.323639 0.510777 0.036 Uiso 1 1 calc R U . . .
H5B H 0.139841 0.197943 0.466439 0.036 Uiso 1 1 calc R U . . .
C6 C 0.2295(3) 0.2788(2) 0.6021(2) 0.0294(5) Uani 1 1 d . . . . .
H6 H 0.153203 0.262712 0.679938 0.035 Uiso 1 1 calc R U . . .
C7 C 0.2685(3) 0.4121(2) 0.5626(2) 0.0292(5) Uani 1 1 d . . . . .
H7A H 0.394071 0.434125 0.579476 0.035 Uiso 1 1 calc R U . . .
H7B H 0.150597 0.477862 0.584012 0.035 Uiso 1 1 calc R U . . .
C8 C 0.2786(3) 0.4516(2) 0.3442(2) 0.0295(5) Uani 1 1 d D . . . .
C13 C 0.8473(3) 0.0876(2) 0.7252(2) 0.0286(5) Uani 1 1 d . . . . .
C14 C 1.0295(4) 0.0064(2) 0.7043(2) 0.0337(6) Uani 1 1 d . . . . .
H14 H 1.056893 -0.048440 0.643752 0.040 Uiso 1 1 calc R U . . .
C15 C 1.1713(4) 0.0057(2) 0.7720(2) 0.0369(6) Uani 1 1 d . . . . .
H15 H 1.296437 -0.049090 0.756500 0.044 Uiso 1 1 calc R U . . .
C16 C 1.1338(4) 0.0832(2) 0.8616(2) 0.0362(6) Uani 1 1 d . . . . .
C17 C 0.9499(4) 0.1632(2) 0.8837(2) 0.0338(6) Uani 1 1 d . . . . .
H17 H 0.921122 0.216096 0.945712 0.041 Uiso 1 1 calc R U . . .
C18 C 0.8082(4) 0.1659(2) 0.8151(2) 0.0315(5) Uani 1 1 d . . . . .
H18 H 0.684039 0.221586 0.829911 0.038 Uiso 1 1 calc R U . . .
C19 C 1.2899(5) 0.0823(3) 0.9349(3) 0.0459(7) Uani 1 1 d . . . . .
H19A H 1.248028 0.038318 1.006894 0.069 Uiso 1 1 calc R U . . .
H19B H 1.300778 0.167804 0.948897 0.069 Uiso 1 1 calc R U . . .
H19C H 1.421834 0.040371 0.896312 0.069 Uiso 1 1 calc R U . . .
O4A O 0.4240(12) 0.3489(6) 0.0306(6) 0.0552(19) Uani 0.318(4) 1 d D . P A 2
N2A N 0.211(6) 0.4136(18) 0.2565(19) 0.027(4) Uani 0.318(4) 1 d D . P A 2
C9A C 0.261(3) 0.2876(17) 0.2143(17) 0.046(5) Uani 0.318(4) 1 d D . P A 2
H9AA H 0.146472 0.269982 0.182083 0.055 Uiso 0.318(4) 1 calc R U P A 2
H9AB H 0.275749 0.227858 0.278392 0.055 Uiso 0.318(4) 1 calc R U P A 2
C10A C 0.4574(15) 0.2675(8) 0.1233(7) 0.048(2) Uani 0.318(4) 1 d D . P A 2
H10C H 0.573363 0.286035 0.153322 0.057 Uiso 0.318(4) 1 calc R U P A 2
H10D H 0.487532 0.180413 0.099948 0.057 Uiso 0.318(4) 1 calc R U P A 2
C11A C 0.3826(14) 0.4733(8) 0.0638(8) 0.047(2) Uani 0.318(4) 1 d D . P A 2
H11A H 0.361870 0.528433 -0.002519 0.056 Uiso 0.318(4) 1 calc R U P A 2
H11B H 0.501960 0.493168 0.089621 0.056 Uiso 0.318(4) 1 calc R U P A 2
C12A C 0.191(3) 0.5007(18) 0.1607(15) 0.042(4) Uani 0.318(4) 1 d D . P A 2
H12C H 0.176662 0.586635 0.185048 0.050 Uiso 0.318(4) 1 calc R U P A 2
H12D H 0.067243 0.492365 0.132466 0.050 Uiso 0.318(4) 1 calc R U P A 2
O4 O 0.0124(7) 0.3658(3) 0.0899(3) 0.0664(12) Uani 0.682(4) 1 d D . P A 1
N2 N 0.251(3) 0.4119(9) 0.2463(9) 0.037(3) Uani 0.682(4) 1 d D . P A 1
C9 C 0.204(2) 0.5017(12) 0.1567(10) 0.078(4) Uani 0.682(4) 1 d D . P A 1
H9A H 0.313984 0.488830 0.089303 0.093 Uiso 0.682(4) 1 calc R U P A 1
H9B H 0.196645 0.586711 0.181976 0.093 Uiso 0.682(4) 1 calc R U P A 1
C10 C 0.0010(14) 0.4879(5) 0.1256(7) 0.104(3) Uani 0.682(4) 1 d D . P A 1
H10A H -0.110191 0.504318 0.191888 0.124 Uiso 0.682(4) 1 calc R U P A 1
H10B H -0.027960 0.548782 0.064325 0.124 Uiso 0.682(4) 1 calc R U P A 1
C11 C 0.0450(8) 0.2795(4) 0.1798(4) 0.0500(11) Uani 0.682(4) 1 d D . P A 1
H12A H 0.047112 0.194969 0.155002 0.060 Uiso 0.682(4) 1 calc R U P A 1
H12B H -0.070284 0.296337 0.243929 0.060 Uiso 0.682(4) 1 calc R U P A 1
C12 C 0.2467(17) 0.2834(9) 0.2213(8) 0.047(2) Uani 0.682(4) 1 d D . P A 1
H13A H 0.253025 0.229175 0.289779 0.057 Uiso 0.682(4) 1 calc R U P A 1
H13B H 0.364841 0.253679 0.162069 0.057 Uiso 0.682(4) 1 calc R U P A 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.220(3) . ?
O2 C3 1.199(3) . ?
O3 C8 1.232(3) . ?
N1 H1 0.86(3) . ?
N1 C1 1.355(3) . ?
N1 C2 1.446(3) . ?
C1 C13 1.506(3) . ?
C2 H2 1.0000 . ?
C2 C3 1.539(4) . ?
C2 C6 1.534(3) . ?
C3 C4 1.528(3) . ?
C4 C5 1.578(3) . ?
C4 C7 1.566(3) . ?
C4 C8 1.498(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.546(3) . ?
C6 H6 1.0000 . ?
C6 C7 1.552(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N2A 1.357(14) . ?
C8 N2 1.351(7) . ?
C13 C14 1.390(3) . ?
C13 C18 1.390(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.389(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.382(4) . ?
C16 C17 1.393(4) . ?
C16 C19 1.517(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.392(3) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
O4A C10A 1.415(9) . ?
O4A C11A 1.414(10) . ?
N2A C9A 1.467(14) . ?
N2A C12A 1.462(13) . ?
C9A H9AA 0.9900 . ?
C9A H9AB 0.9900 . ?
C9A C10A 1.549(18) . ?
C10A H10C 0.9900 . ?
C10A H10D 0.9900 . ?
C11A H11A 0.9900 . ?
C11A H11B 0.9900 . ?
C11A C12A 1.574(16) . ?
C12A H12C 0.9900 . ?
C12A H12D 0.9900 . ?
O4 C10 1.420(6) . ?
O4 C11 1.418(6) . ?
N2 C9 1.460(8) . ?
N2 C12 1.466(8) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.541(13) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H12A 0.9900 . ?
C11 H12B 0.9900 . ?
C11 C12 1.566(11) . ?
C12 H13A 0.9900 . ?
C12 H13B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 H1 118(2) . . ?
C1 N1 C2 120.46(19) . . ?
C2 N1 H1 122(2) . . ?
O1 C1 N1 123.4(2) . . ?
O1 C1 C13 120.7(2) . . ?
N1 C1 C13 115.9(2) . . ?
N1 C2 H2 109.4 . . ?
N1 C2 C3 113.94(19) . . ?
N1 C2 C6 116.4(2) . . ?
C3 C2 H2 109.4 . . ?
C6 C2 H2 109.4 . . ?
C6 C2 C3 97.63(17) . . ?
O2 C3 C2 129.0(2) . . ?
O2 C3 C4 128.6(2) . . ?
C4 C3 C2 102.28(19) . . ?
C3 C4 C5 100.56(17) . . ?
C3 C4 C7 97.64(18) . . ?
C7 C4 C5 85.52(18) . . ?
C8 C4 C3 119.9(2) . . ?
C8 C4 C5 126.28(19) . . ?
C8 C4 C7 119.01(19) . . ?
C4 C5 H5A 114.8 . . ?
C4 C5 H5B 114.8 . . ?
H5A C5 H5B 111.9 . . ?
C6 C5 C4 83.09(16) . . ?
C6 C5 H5A 114.8 . . ?
C6 C5 H5B 114.8 . . ?
C2 C6 C5 100.61(19) . . ?
C2 C6 H6 120.0 . . ?
C2 C6 C7 102.85(18) . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 87.12(17) . . ?
C7 C6 H6 120.0 . . ?
C4 C7 H7A 114.8 . . ?
C4 C7 H7B 114.8 . . ?
C6 C7 C4 83.29(17) . . ?
C6 C7 H7A 114.8 . . ?
C6 C7 H7B 114.8 . . ?
H7A C7 H7B 111.8 . . ?
O3 C8 C4 119.4(2) . . ?
O3 C8 N2A 122.7(9) . . ?
O3 C8 N2 121.2(5) . . ?
N2A C8 C4 116.8(10) . . ?
N2 C8 C4 119.4(5) . . ?
C14 C13 C1 118.1(2) . . ?
C14 C13 C18 119.3(2) . . ?
C18 C13 C1 122.5(2) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.9(2) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.4 . . ?
C16 C15 C14 121.2(2) . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C17 118.9(2) . . ?
C15 C16 C19 120.9(3) . . ?
C17 C16 C19 120.2(3) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.2(2) . . ?
C18 C17 H17 119.9 . . ?
C13 C18 C17 120.4(2) . . ?
C13 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C11A O4A C10A 110.3(7) . . ?
C8 N2A C9A 125(2) . . ?
C8 N2A C12A 118.3(17) . . ?
C12A N2A C9A 108.2(16) . . ?
N2A C9A H9AA 108.9 . . ?
N2A C9A H9AB 108.9 . . ?
N2A C9A C10A 113(2) . . ?
H9AA C9A H9AB 107.7 . . ?
C10A C9A H9AA 108.9 . . ?
C10A C9A H9AB 108.9 . . ?
O4A C10A C9A 106.9(10) . . ?
O4A C10A H10C 110.3 . . ?
O4A C10A H10D 110.3 . . ?
C9A C10A H10C 110.3 . . ?
C9A C10A H10D 110.3 . . ?
H10C C10A H10D 108.6 . . ?
O4A C11A H11A 108.9 . . ?
O4A C11A H11B 108.9 . . ?
O4A C11A C12A 113.4(10) . . ?
H11A C11A H11B 107.7 . . ?
C12A C11A H11A 108.9 . . ?
C12A C11A H11B 108.9 . . ?
N2A C12A C11A 109.8(19) . . ?
N2A C12A H12C 109.7 . . ?
N2A C12A H12D 109.7 . . ?
C11A C12A H12C 109.7 . . ?
C11A C12A H12D 109.7 . . ?
H12C C12A H12D 108.2 . . ?
C11 O4 C10 109.5(4) . . ?
C8 N2 C9 119.9(8) . . ?
C8 N2 C12 126.2(8) . . ?
C9 N2 C12 113.8(8) . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
N2 C9 C10 110.7(10) . . ?
H9A C9 H9B 108.1 . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
O4 C10 C9 109.3(7) . . ?
O4 C10 H10A 109.8 . . ?
O4 C10 H10B 109.8 . . ?
C9 C10 H10A 109.8 . . ?
C9 C10 H10B 109.8 . . ?
H10A C10 H10B 108.3 . . ?
O4 C11 H12A 108.8 . . ?
O4 C11 H12B 108.8 . . ?
O4 C11 C12 113.7(5) . . ?
H12A C11 H12B 107.7 . . ?
C12 C11 H12A 108.8 . . ?
C12 C11 H12B 108.8 . . ?
N2 C12 C11 108.1(8) . . ?
N2 C12 H13A 110.1 . . ?
N2 C12 H13B 110.1 . . ?
C11 C12 H13A 110.1 . . ?
C11 C12 H13B 110.1 . . ?
H13A C12 H13B 108.4 . . ?

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
O1 C1 C13 C14 37.4(3) . . . . ?
O1 C1 C13 C18 -140.0(3) . . . . ?
O2 C3 C4 C5 145.5(3) . . . . ?
O2 C3 C4 C7 -127.7(3) . . . . ?
O2 C3 C4 C8 2.2(4) . . . . ?
O3 C8 N2A C9A 154(2) . . . . ?
O3 C8 N2A C12A 11(4) . . . . ?
O3 C8 N2 C9 -10.9(19) . . . . ?
O3 C8 N2 C12 174.2(11) . . . . ?
N1 C1 C13 C14 -143.9(2) . . . . ?
N1 C1 C13 C18 38.7(3) . . . . ?
N1 C2 C3 O2 47.2(3) . . . . ?
N1 C2 C3 C4 -128.73(19) . . . . ?
N1 C2 C6 C5 170.93(19) . . . . ?
N1 C2 C6 C7 81.5(2) . . . . ?
C1 N1 C2 C3 -114.3(2) . . . . ?
C1 N1 C2 C6 133.2(2) . . . . ?
C1 C13 C14 C15 -178.5(2) . . . . ?
C1 C13 C18 C17 177.4(2) . . . . ?
C2 N1 C1 O1 -0.1(4) . . . . ?
C2 N1 C1 C13 -178.7(2) . . . . ?
C2 C3 C4 C5 -38.5(2) . . . . ?
C2 C3 C4 C7 48.30(19) . . . . ?
C2 C3 C4 C8 178.19(19) . . . . ?
C2 C6 C7 C4 66.17(18) . . . . ?
C3 C2 C6 C5 49.38(19) . . . . ?
C3 C2 C6 C7 -40.1(2) . . . . ?
C3 C4 C5 C6 63.45(18) . . . . ?
C3 C4 C7 C6 -66.75(17) . . . . ?
C3 C4 C8 O3 -103.5(3) . . . . ?
C3 C4 C8 N2A 88.5(18) . . . . ?
C3 C4 C8 N2 75.8(9) . . . . ?
C4 C5 C6 C2 -68.76(17) . . . . ?
C4 C5 C6 C7 33.77(16) . . . . ?
C4 C8 N2A C9A -38(4) . . . . ?
C4 C8 N2A C12A 178.2(19) . . . . ?
C4 C8 N2 C9 169.8(11) . . . . ?
C4 C8 N2 C12 -5(2) . . . . ?
C5 C4 C7 C6 33.33(15) . . . . ?
C5 C4 C8 O3 123.3(3) . . . . ?
C5 C4 C8 N2A -44.7(18) . . . . ?
C5 C4 C8 N2 -57.4(9) . . . . ?
C5 C6 C7 C4 -34.05(16) . . . . ?
C6 C2 C3 O2 170.6(2) . . . . ?
C6 C2 C3 C4 -5.4(2) . . . . ?
C7 C4 C5 C6 -33.50(15) . . . . ?
C7 C4 C8 O3 16.1(3) . . . . ?
C7 C4 C8 N2A -151.9(18) . . . . ?
C7 C4 C8 N2 -164.6(9) . . . . ?
C8 C4 C5 C6 -156.6(2) . . . . ?
C8 C4 C7 C6 162.8(2) . . . . ?
C8 N2A C9A C10A -88(3) . . . . ?
C8 N2A C12A C11A 98(3) . . . . ?
C8 N2 C9 C10 -121.7(13) . . . . ?
C8 N2 C12 C11 126.3(14) . . . . ?
C13 C14 C15 C16 1.0(4) . . . . ?
C14 C13 C18 C17 0.0(4) . . . . ?
C14 C15 C16 C17 0.0(4) . . . . ?
C14 C15 C16 C19 -179.7(2) . . . . ?
C15 C16 C17 C18 -1.0(4) . . . . ?
C16 C17 C18 C13 1.0(4) . . . . ?
C18 C13 C14 C15 -1.0(4) . . . . ?
C19 C16 C17 C18 178.7(2) . . . . ?
O4A C11A C12A N2A 54.2(18) . . . . ?
N2A C9A C10A O4A -62.4(19) . . . . ?
C9A N2A C12A C11A -51(3) . . . . ?
C10A O4A C11A C12A -59.4(12) . . . . ?
C11A O4A C10A C9A 60.5(13) . . . . ?
C12A N2A C9A C10A 58(3) . . . . ?
O4 C11 C12 N2 52.7(9) . . . . ?
N2 C9 C10 O4 -58.9(12) . . . . ?
C9 N2 C12 C11 -48.9(16) . . . . ?
C10 O4 C11 C12 -60.8(7) . . . . ?
C11 O4 C10 C9 62.0(9) . . . . ?
C12 N2 C9 C10 53.8(17) . . . . ?

_olex2_date_sample_data_collection 2023-02-15
_olex2_exptl_crystal_mounting_method 'mounted in a polyimide loop'
_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 1.379
_oxdiff_exptl_absorpt_empirical_full_min 0.636
####################################################################### 
# 
# 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_kjw-2023-423
_database_code_depnum_ccdc_archive 'CCDC 2298459'
loop_
_audit_author_name
_audit_author_address
'Nathan D. Schley'
;Vanderbilt University
United States of America
;
_audit_update_record             
;
2023-09-29 deposited with the CCDC.	2023-10-10 downloaded from the CCDC.
;
_audit_creation_date             2023-09-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H24 N2 O3'
_chemical_formula_sum            'C18 H24 N2 O3'
_chemical_formula_weight         316.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         C18H25N2O3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   15.9398(2)
_cell_length_b                   12.0803(2)
_cell_length_c                   16.6377(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3203.72(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    11115
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      71.6720
_cell_measurement_theta_min      5.2750
_shelx_estimated_absorpt_T_max   0.938
_shelx_estimated_absorpt_T_min   0.840
_exptl_absorpt_coefficient_mu    0.722
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.598
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.71a (Rigaku Oxford Diffraction, 2022)
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 -7 -3 0.0638
-2 7 3 0.1015
-8 -4 5 0.1048
4 4 -8 0.0746
6 -1 9 0.0343
-4 3 -9 0.0319

_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.09
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
2.5470 -7.3187 -2.7940 0.4179 0.8768 -0.2378
-2.4955 7.3292 2.7924 -0.4174 -0.8757 0.2428
-8.0085 -3.5119 4.8478 0.3809 -0.2933 -0.8769
4.0856 4.2956 -7.9815 -0.7678 0.2705 0.5808
5.6959 -1.3097 8.8377 0.8760 -0.2103 0.4340
-4.3548 2.9582 -8.9183 -0.9672 0.1264 -0.2202

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18157
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.618
_diffrn_reflns_theta_min         5.308
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1506
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -108.00 -39.00   1.00    1.00    --  -35.84-178.00  30.00   69
  2  ω   -107.00  -6.00   1.00    1.00    --  -35.84 -19.00 -60.00  101
  3  ω   -105.00 -17.00   1.00    1.00    --  -35.84 -38.00 150.00   88
  4  ω   -108.00 -39.00   1.00    1.00    --  -35.84-178.00 120.00   69
  5  ω     61.00 108.00   1.00    1.00    --   35.84 178.00 150.00   47
  6  ω     19.00 103.00   1.00    1.00    --   35.84  57.00  60.00   84
  7  ω      6.00  74.00   1.00    1.00    --   35.84 -99.00 -30.00   68
  8  ω     58.00 108.00   1.00    1.00    --   35.84-178.00-150.00   50
  9  ω     40.00 126.00   1.00    2.00    --  108.40 -45.00  60.00   86
 10  ω    103.00 176.00   1.00    2.00    --  108.40  77.00  90.00   73
 11  ω    103.00 176.00   1.00    2.00    --  108.40  77.00  30.00   73
 12  ω     40.00 124.00   1.00    2.00    --  108.40-140.00 -70.00   84
 13  ω    104.00 175.00   1.00    2.00    --  108.40 111.00  60.00   71
 14  ω     39.00 107.00   1.00    2.00    --  108.40 -94.00   0.00   68
 15  ω     39.00 107.00   1.00    2.00    --  108.40 -94.00 150.00   68
 16  ω     42.00 126.00   1.00    2.00    --  108.40 -61.00   0.00   84
 17  ω     39.00 107.00   1.00    2.00    --  108.40 -94.00 -90.00   68
 18  ω   -105.00 -17.00   1.00    1.00    --  -35.84 -38.00-120.00   88
 19  ω    -55.00  -1.00   1.00    1.00    --  -35.84  38.00 -30.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0276042000
_diffrn_orient_matrix_UB_12      -0.0743363000
_diffrn_orient_matrix_UB_13      0.0703169000
_diffrn_orient_matrix_UB_21      0.0370496000
_diffrn_orient_matrix_UB_22      -0.0839609000
_diffrn_orient_matrix_UB_23      -0.0601170000
_diffrn_orient_matrix_UB_31      0.0849046000
_diffrn_orient_matrix_UB_32      0.0607507000
_diffrn_orient_matrix_UB_33      0.0033883000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2857
_reflns_number_total             3106
_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 1.171.42.71a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.71a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.71a (Rigaku OD, 2022)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3106
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.043
_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)+(0.0405P)²+1.3355P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.0952
_refine_special_details          
'Hydrogen atoms on the bicyclic ring and N and O were located in the difference map and refined without restraint. The remaining hydrogens were refined using the riding model.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
;
_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 0.69090(6) 0.86168(8) 0.56815(6) 0.0230(2) Uani 1 1 d . . . . .
O2 O 0.60042(6) 0.56184(7) 0.49362(5) 0.0182(2) Uani 1 1 d . . . . .
H2 H 0.5497(14) 0.5608(17) 0.4589(14) 0.059(6) Uiso 1 1 d . . . . .
O3 O 0.82692(6) 0.69362(8) 0.34537(6) 0.0266(2) Uani 1 1 d . . . . .
N1 N 0.76756(7) 0.73262(9) 0.50334(7) 0.0186(2) Uani 1 1 d . . . . .
N2 N 0.53357(7) 0.44241(9) 0.61243(6) 0.0180(2) Uani 1 1 d . . . . .
H2A H 0.5832(11) 0.4205(14) 0.5884(10) 0.029(4) Uiso 1 1 d . . . . .
C1 C 0.70706(8) 0.76305(10) 0.55596(7) 0.0159(3) Uani 1 1 d . . . . .
C2 C 0.65792(8) 0.67700(10) 0.60193(7) 0.0163(3) Uani 1 1 d . . . . .
C3 C 0.57936(8) 0.62772(10) 0.56092(8) 0.0171(3) Uani 1 1 d . . . . .
H3 H 0.5389(9) 0.6842(12) 0.5440(9) 0.014(3) Uiso 1 1 d . . . . .
C4 C 0.54360(8) 0.55919(10) 0.63421(8) 0.0173(3) Uani 1 1 d . . . . .
H4 H 0.4867(10) 0.5865(12) 0.6524(9) 0.018(4) Uiso 1 1 d . . . . .
C5 C 0.61042(8) 0.58880(11) 0.69735(8) 0.0194(3) Uani 1 1 d . . . . .
H5 H 0.6043(10) 0.5588(13) 0.7504(11) 0.026(4) Uiso 1 1 d . . . . .
C6 C 0.69365(8) 0.57637(11) 0.65013(8) 0.0180(3) Uani 1 1 d . . . . .
H6A H 0.7405(10) 0.5978(13) 0.6822(9) 0.018(4) Uiso 1 1 d . . . . .
H6B H 0.7044(9) 0.5085(13) 0.6226(10) 0.020(4) Uiso 1 1 d . . . . .
C7 C 0.61829(8) 0.71485(11) 0.68255(8) 0.0200(3) Uani 1 1 d . . . . .
H7A H 0.5641(10) 0.7599(14) 0.6791(10) 0.027(4) Uiso 1 1 d . . . . .
H7B H 0.6619(10) 0.7512(13) 0.7180(10) 0.023(4) Uiso 1 1 d . . . . .
C8 C 0.81543(9) 0.81675(11) 0.46006(9) 0.0231(3) Uani 1 1 d . . . . .
H8A H 0.875770 0.809688 0.473197 0.028 Uiso 1 1 calc R U . . .
H8B H 0.796526 0.891443 0.476535 0.028 Uiso 1 1 calc R U . . .
C9 C 0.80254(9) 0.80193(11) 0.37051(9) 0.0251(3) Uani 1 1 d . . . . .
H9A H 0.742693 0.814046 0.357242 0.030 Uiso 1 1 calc R U . . .
H9B H 0.836078 0.857753 0.341091 0.030 Uiso 1 1 calc R U . . .
C10 C 0.77954(9) 0.61118(11) 0.38730(8) 0.0227(3) Uani 1 1 d . . . . .
H10A H 0.798051 0.536825 0.369660 0.027 Uiso 1 1 calc R U . . .
H10B H 0.719436 0.619153 0.373458 0.027 Uiso 1 1 calc R U . . .
C11 C 0.79003(8) 0.62069(10) 0.47808(8) 0.0198(3) Uani 1 1 d . . . . .
H11A H 0.753441 0.566162 0.505360 0.024 Uiso 1 1 calc R U . . .
H11B H 0.848909 0.604778 0.493097 0.024 Uiso 1 1 calc R U . . .
C12 C 0.51581(9) 0.36987(11) 0.68165(8) 0.0217(3) Uani 1 1 d . . . . .
H12A H 0.461108 0.390349 0.705592 0.026 Uiso 1 1 calc R U . . .
H12B H 0.559685 0.380043 0.723112 0.026 Uiso 1 1 calc R U . . .
C13 C 0.51367(8) 0.25029(11) 0.65563(7) 0.0184(3) Uani 1 1 d . . . . .
C14 C 0.44854(8) 0.20985(11) 0.60781(8) 0.0190(3) Uani 1 1 d . . . . .
H14 H 0.404368 0.257982 0.592055 0.023 Uiso 1 1 calc R U . . .
C15 C 0.44755(8) 0.10030(11) 0.58304(8) 0.0212(3) Uani 1 1 d . . . . .
H15 H 0.403363 0.074226 0.549729 0.025 Uiso 1 1 calc R U . . .
C16 C 0.51093(9) 0.02858(11) 0.60674(8) 0.0224(3) Uani 1 1 d . . . . .
H16 H 0.509689 -0.046844 0.590632 0.027 Uiso 1 1 calc R U . . .
C17 C 0.57592(9) 0.06769(12) 0.65401(8) 0.0241(3) Uani 1 1 d . . . . .
H17 H 0.619500 0.018959 0.670305 0.029 Uiso 1 1 calc R U . . .
C18 C 0.57770(8) 0.17787(12) 0.67770(8) 0.0222(3) Uani 1 1 d . . . . .
H18 H 0.623119 0.204206 0.709339 0.027 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2357(16) . ?
O2 H2 0.99(2) . ?
O2 C3 1.4141(15) . ?
O3 C9 1.4275(17) . ?
O3 C10 1.4314(16) . ?
N1 C1 1.3534(16) . ?
N1 C8 1.4606(16) . ?
N1 C11 1.4606(16) . ?
N2 H2A 0.925(18) . ?
N2 C4 1.4653(16) . ?
N2 C12 1.4746(16) . ?
C1 C2 1.5098(17) . ?
C2 C3 1.5452(17) . ?
C2 C6 1.5636(17) . ?
C2 C7 1.5515(17) . ?
C3 H3 0.980(15) . ?
C3 C4 1.5803(17) . ?
C4 H4 1.011(15) . ?
C4 C5 1.5381(18) . ?
C5 H5 0.960(17) . ?
C5 C6 1.5491(18) . ?
C5 C7 1.5477(18) . ?
C6 H6A 0.953(16) . ?
C6 H6B 0.955(16) . ?
C7 H7A 1.023(16) . ?
C7 H7B 1.012(16) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.515(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5239(19) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.5084(18) . ?
C13 C14 1.3963(18) . ?
C13 C18 1.3936(19) . ?
C14 H14 0.9500 . ?
C14 C15 1.3861(19) . ?
C15 H15 0.9500 . ?
C15 C16 1.388(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.384(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.388(2) . ?
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
C3 O2 H2 106.0(13) . . ?
C9 O3 C10 110.57(10) . . ?
C1 N1 C8 120.14(11) . . ?
C1 N1 C11 127.76(11) . . ?
C11 N1 C8 111.97(10) . . ?
C4 N2 H2A 106.8(11) . . ?
C4 N2 C12 113.57(10) . . ?
C12 N2 H2A 109.4(11) . . ?
O1 C1 N1 121.11(12) . . ?
O1 C1 C2 118.20(11) . . ?
N1 C1 C2 120.69(11) . . ?
C1 C2 C3 117.51(10) . . ?
C1 C2 C6 127.31(11) . . ?
C1 C2 C7 116.50(10) . . ?
C3 C2 C6 102.83(10) . . ?
C3 C2 C7 99.52(10) . . ?
C7 C2 C6 86.22(9) . . ?
O2 C3 C2 111.97(10) . . ?
O2 C3 H3 108.7(9) . . ?
O2 C3 C4 113.69(10) . . ?
C2 C3 H3 113.1(8) . . ?
C2 C3 C4 98.82(10) . . ?
C4 C3 H3 110.4(9) . . ?
N2 C4 C3 110.66(10) . . ?
N2 C4 H4 106.9(9) . . ?
N2 C4 C5 117.93(11) . . ?
C3 C4 H4 112.6(8) . . ?
C5 C4 C3 98.94(10) . . ?
C5 C4 H4 109.9(8) . . ?
C4 C5 H5 118.0(10) . . ?
C4 C5 C6 102.95(10) . . ?
C4 C5 C7 100.15(10) . . ?
C6 C5 H5 121.2(10) . . ?
C7 C5 H5 121.8(9) . . ?
C7 C5 C6 86.86(10) . . ?
C2 C6 H6A 111.2(9) . . ?
C2 C6 H6B 119.1(9) . . ?
C5 C6 C2 82.69(9) . . ?
C5 C6 H6A 111.1(9) . . ?
C5 C6 H6B 118.7(9) . . ?
H6A C6 H6B 111.2(13) . . ?
C2 C7 H7A 116.9(9) . . ?
C2 C7 H7B 110.6(9) . . ?
C5 C7 C2 83.14(9) . . ?
C5 C7 H7A 117.7(9) . . ?
C5 C7 H7B 113.0(9) . . ?
H7A C7 H7B 112.5(13) . . ?
N1 C8 H8A 109.8 . . ?
N1 C8 H8B 109.8 . . ?
N1 C8 C9 109.38(11) . . ?
H8A C8 H8B 108.2 . . ?
C9 C8 H8A 109.8 . . ?
C9 C8 H8B 109.8 . . ?
O3 C9 C8 111.07(11) . . ?
O3 C9 H9A 109.4 . . ?
O3 C9 H9B 109.4 . . ?
C8 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
O3 C10 H10A 109.2 . . ?
O3 C10 H10B 109.2 . . ?
O3 C10 C11 111.88(11) . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
N1 C11 C10 109.15(11) . . ?
N1 C11 H11A 109.9 . . ?
N1 C11 H11B 109.9 . . ?
C10 C11 H11A 109.9 . . ?
C10 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
N2 C12 H12A 109.6 . . ?
N2 C12 H12B 109.6 . . ?
N2 C12 C13 110.45(10) . . ?
H12A C12 H12B 108.1 . . ?
C13 C12 H12A 109.6 . . ?
C13 C12 H12B 109.6 . . ?
C14 C13 C12 121.03(12) . . ?
C18 C13 C12 120.60(12) . . ?
C18 C13 C14 118.36(12) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.79(12) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.21(12) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.56(13) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.25(13) . . ?
C18 C17 H17 119.9 . . ?
C13 C18 H18 119.6 . . ?
C17 C18 C13 120.81(13) . . ?
C17 C18 H18 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 94.16(14) . . . . ?
O1 C1 C2 C6 -130.46(13) . . . . ?
O1 C1 C2 C7 -23.76(17) . . . . ?
O2 C3 C4 N2 -5.02(14) . . . . ?
O2 C3 C4 C5 119.45(11) . . . . ?
O3 C10 C11 N1 55.48(14) . . . . ?
N1 C1 C2 C3 -86.34(15) . . . . ?
N1 C1 C2 C6 49.04(18) . . . . ?
N1 C1 C2 C7 155.74(12) . . . . ?
N1 C8 C9 O3 -57.69(15) . . . . ?
N2 C4 C5 C6 74.49(13) . . . . ?
N2 C4 C5 C7 163.58(11) . . . . ?
N2 C12 C13 C14 -70.01(16) . . . . ?
N2 C12 C13 C18 108.84(14) . . . . ?
C1 N1 C8 C9 -119.77(13) . . . . ?
C1 N1 C11 C10 120.80(14) . . . . ?
C1 C2 C3 O2 67.89(14) . . . . ?
C1 C2 C3 C4 -172.04(10) . . . . ?
C1 C2 C6 C5 154.43(12) . . . . ?
C1 C2 C7 C5 -163.86(11) . . . . ?
C2 C3 C4 N2 -123.81(11) . . . . ?
C2 C3 C4 C5 0.66(11) . . . . ?
C3 C2 C6 C5 -65.28(10) . . . . ?
C3 C2 C7 C5 68.76(10) . . . . ?
C3 C4 C5 C6 -44.69(11) . . . . ?
C3 C4 C5 C7 44.40(11) . . . . ?
C4 N2 C12 C13 -175.17(11) . . . . ?
C4 C5 C6 C2 66.00(10) . . . . ?
C4 C5 C7 C2 -68.64(10) . . . . ?
C6 C2 C3 O2 -77.15(12) . . . . ?
C6 C2 C3 C4 42.92(11) . . . . ?
C6 C2 C7 C5 -33.63(9) . . . . ?
C6 C5 C7 C2 33.97(9) . . . . ?
C7 C2 C3 O2 -165.42(10) . . . . ?
C7 C2 C3 C4 -45.34(11) . . . . ?
C7 C2 C6 C5 33.63(9) . . . . ?
C7 C5 C6 C2 -33.70(9) . . . . ?
C8 N1 C1 O1 0.32(19) . . . . ?
C8 N1 C1 C2 -179.16(11) . . . . ?
C8 N1 C11 C10 -55.07(14) . . . . ?
C9 O3 C10 C11 -58.00(15) . . . . ?
C10 O3 C9 C8 58.85(15) . . . . ?
C11 N1 C1 O1 -175.26(12) . . . . ?
C11 N1 C1 C2 5.3(2) . . . . ?
C11 N1 C8 C9 56.46(15) . . . . ?
C12 N2 C4 C3 169.10(10) . . . . ?
C12 N2 C4 C5 56.28(15) . . . . ?
C12 C13 C14 C15 178.99(12) . . . . ?
C12 C13 C18 C17 179.89(12) . . . . ?
C13 C14 C15 C16 1.10(19) . . . . ?
C14 C13 C18 C17 -1.23(19) . . . . ?
C14 C15 C16 C17 -1.22(19) . . . . ?
C15 C16 C17 C18 0.1(2) . . . . ?
C16 C17 C18 C13 1.1(2) . . . . ?
C18 C13 C14 C15 0.12(19) . . . . ?

_olex2_date_sample_data_collection 2023-09-27
_olex2_exptl_crystal_mounting_method 'mounted in a polyimide loop'
_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 1.154
_oxdiff_exptl_absorpt_empirical_full_min 0.900
