# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_22kaw14_a
_database_code_depnum_ccdc_archive 'CCDC 2312799'
loop_
_audit_author_name
_audit_author_address
'Kraig Wheeler'
;Whitworth University
United States of America
;
_audit_update_record             
;
2023-12-08 deposited with the CCDC.	2024-02-12 downloaded from the CCDC.
;
_audit_creation_date             2023-11-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_chemical_formula_moiety         'C14 H19 N O3'
_chemical_formula_sum            'C14 H19 N O3'
_chemical_formula_weight         249.312
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01788 0.00908 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.03110 0.01806 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.04960 0.03233 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   8.4622(7)
_cell_length_b                   17.4106(13)
_cell_length_c                   10.0167(7)
_cell_angle_alpha                90
_cell_angle_beta                 109.344(5)
_cell_angle_gamma                90
_cell_volume                     1392.47(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4949
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.50
_cell_measurement_theta_min      5.08
_exptl_absorpt_coefficient_mu    0.677
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6252
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             537.834
_exptl_crystal_size_max          0.306
_exptl_crystal_size_mid          0.178
_exptl_crystal_size_min          0.089
_diffrn_reflns_av_R_equivalents  0.1046
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.9992
_diffrn_reflns_Laue_measured_fraction_max 0.9975
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            27050
_diffrn_reflns_point_group_measured_fraction_full 0.9992
_diffrn_reflns_point_group_measured_fraction_max 0.9975
_diffrn_reflns_theta_full        67.6786
_diffrn_reflns_theta_max         72.39
_diffrn_reflns_theta_min         5.08
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.9992
_diffrn_measured_fraction_theta_max 0.9975
_diffrn_measurement_device       'κ-geometry four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'focusing mirror'
_diffrn_radiation_detector       'Bruker PHOTON II'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -10
_reflns_limit_k_max              21
_reflns_limit_k_min              0
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                1945
_reflns_number_total             2753
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT+ V8.40B (Bruker AXS Inc., 2020)'
_computing_data_collection       'APEX5 Ver.2022.08-RC130 (Bruker-AXS, 2023)'
_computing_data_reduction        'SAINT+ Ve8.40B (Bruker-AXS, 2020)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2019/1)'
_computing_structure_solution    'XT (Sheldrick, 2018/2)'
_refine_diff_density_max         0.4413
_refine_diff_density_min         -0.3813
_refine_diff_density_rms         0.0822
_refine_ls_d_res_high            0.8088
_refine_ls_d_res_low             8.7053
_refine_ls_goodness_of_fit_ref   1.0618
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    29
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2753
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0897
_refine_ls_R_factor_gt           0.0559
_refine_ls_restrained_S_all      1.0618
_refine_ls_shift/su_max          -0.0003
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0714P)²+0.6351P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1299
_refine_ls_wR_factor_ref         0.1522
_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron
 density map and refined using anisotropic displacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 of the connected C atoms (1.5xUeqiv for methyl groups). Those H atoms
 attached to nitrogen and oxygen were located in Fourier diff maps
 and assigned Uiso = 1.2xUeqiv.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10a,H10b)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7)
2.d Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c), C13(H13a,H13b,H13c), C14(H14a,H14b,H14c)
;
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_refinement_flags_posn
O1 O 0.6240(2) 0.22661(9) 0.69818(15) 0.0315(4) Uani 1.000000 .
O2 O 0.7181(2) 0.02684(10) 0.59051(18) 0.0385(4) Uani 1.000000 .
H2 H 0.639(4) -0.0102(17) 0.578(3) 0.0462(5) Uiso 1.000000 R
O3 O 0.49258(19) 0.08970(9) 0.45244(16) 0.0327(4) Uani 1.000000 .
N1 N 0.6703(2) 0.22556(11) 0.49039(19) 0.0260(4) Uani 1.000000 .
H1 H 0.641(3) 0.2407(15) 0.410(3) 0.0312(5) Uiso 1.000000 R
C1 C 0.5997(3) 0.25630(13) 0.5806(2) 0.0250(5) Uani 1.000000 .
C2 C 0.4933(3) 0.32573(13) 0.5351(2) 0.0262(5) Uani 1.000000 .
C3 C 0.3976(3) 0.34994(14) 0.6173(2) 0.0315(5) Uani 1.000000 .
H3 H 0.4049(3) 0.32287(14) 0.7015(2) 0.0378(7) Uiso 1.000000 R
C4 C 0.2925(3) 0.41279(15) 0.5777(3) 0.0363(6) Uani 1.000000 .
H4 H 0.2280(3) 0.42797(15) 0.6349(3) 0.0435(7) Uiso 1.000000 R
C5 C 0.2796(3) 0.45417(14) 0.4559(2) 0.0330(5) Uani 1.000000 .
C6 C 0.3797(3) 0.43153(14) 0.3773(2) 0.0363(6) Uani 1.000000 .
H6 H 0.3765(3) 0.46031(14) 0.2958(2) 0.0435(7) Uiso 1.000000 R
C7 C 0.4836(3) 0.36826(14) 0.4146(2) 0.0337(6) Uani 1.000000 .
H7 H 0.5489(3) 0.35362(14) 0.3578(2) 0.0404(7) Uiso 1.000000 R
C8 C 0.6412(3) 0.08764(13) 0.5193(2) 0.0280(5) Uani 1.000000 .
C9 C 0.7608(3) 0.15360(12) 0.5254(2) 0.0271(5) Uani 1.000000 .
H9 H 0.8422(3) 0.15724(12) 0.6238(2) 0.0326(6) Uiso 1.000000 R
C10 C 0.8577(3) 0.13746(13) 0.4239(2) 0.0296(5) Uani 1.000000 .
H10a H 0.8927(3) 0.08292(13) 0.4335(2) 0.0355(6) Uiso 1.000000 R
H10b H 0.7817(3) 0.14524(13) 0.3257(2) 0.0355(6) Uiso 1.000000 R
C11 C 1.0130(3) 0.18795(14) 0.4485(3) 0.0343(6) Uani 1.000000 .
H11 H 0.9832(3) 0.24223(14) 0.4626(3) 0.0412(7) Uiso 1.000000 R
C12 C 1.1528(3) 0.16180(17) 0.5796(3) 0.0461(7) Uani 1.000000 .
H12a H 1.2492(10) 0.1961(7) 0.5966(12) 0.0692(10) Uiso 1.000000 GR
H12b H 1.1136(9) 0.1631(11) 0.6613(5) 0.0692(10) Uiso 1.000000 GR
H12c H 1.1857(17) 0.1093(4) 0.5656(8) 0.0692(10) Uiso 1.000000 GR
C13 C 1.0732(3) 0.18479(17) 0.3208(3) 0.0460(7) Uani 1.000000 .
H13a H 0.9832(9) 0.2021(10) 0.2363(5) 0.0690(10) Uiso 1.000000 GR
H13b H 1.1709(15) 0.2183(8) 0.3374(9) 0.0690(10) Uiso 1.000000 GR
H13c H 1.104(2) 0.1319(3) 0.3068(12) 0.0690(10) Uiso 1.000000 GR
C14 C 0.1616(3) 0.52136(16) 0.4104(3) 0.0436(7) Uani 1.000000 .
H14a H 0.0566(9) 0.5042(3) 0.3400(15) 0.0654(10) Uiso 1.000000 GR
H14b H 0.1384(19) 0.5425(7) 0.4927(4) 0.0654(10) Uiso 1.000000 GR
H14c H 0.2129(10) 0.5611(5) 0.3688(18) 0.0654(10) Uiso 1.000000 GR


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 1.239(2) . ?
O2 H2 0.91(3) . ?
O2 C8 1.321(3) . ?
O3 C8 1.214(3) . ?
N1 H1 0.81(3) . ?
N1 C1 1.348(3) . ?
N1 C9 1.449(3) . ?
C1 C2 1.486(3) . ?
C2 C3 1.398(3) . ?
C2 C7 1.396(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.390(3) . ?
C5 C6 1.391(3) . ?
C5 C14 1.507(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.381(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.518(3) . ?
C9 H9 1.0000 . ?
C9 C10 1.529(3) . ?
C10 H10a 0.9900 . ?
C10 H10b 0.9900 . ?
C10 C11 1.532(3) . ?
C11 H11 1.0000 . ?
C11 C12 1.517(4) . ?
C11 C13 1.527(3) . ?
C12 H12a 0.9800 . ?
C12 H12b 0.9800 . ?
C12 H12c 0.9800 . ?
C13 H13a 0.9800 . ?
C13 H13b 0.9800 . ?
C13 H13c 0.9800 . ?
C14 H14a 0.9800 . ?
C14 H14b 0.9800 . ?
C14 H14c 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O2 H2 106.7(17) . . ?
C1 N1 H1 119.2(18) . . ?
C9 N1 H1 119.0(18) . . ?
C9 N1 C1 119.77(18) . . ?
N1 C1 O1 120.0(2) . . ?
C2 C1 O1 121.61(18) . . ?
C2 C1 N1 118.36(18) . . ?
C3 C2 C1 118.35(19) . . ?
C7 C2 C1 123.60(19) . . ?
C7 C2 C3 118.0(2) . . ?
H3 C3 C2 119.58(13) . . ?
C4 C3 C2 120.8(2) . . ?
C4 C3 H3 119.58(12) . . ?
H4 C4 C3 119.39(12) . . ?
C5 C4 C3 121.2(2) . . ?
C5 C4 H4 119.39(14) . . ?
C6 C5 C4 117.7(2) . . ?
C14 C5 C4 121.3(2) . . ?
C14 C5 C6 121.0(2) . . ?
H6 C6 C5 119.16(14) . . ?
C7 C6 C5 121.7(2) . . ?
C7 C6 H6 119.16(13) . . ?
C6 C7 C2 120.5(2) . . ?
H7 C7 C2 119.77(13) . . ?
H7 C7 C6 119.77(13) . . ?
O3 C8 O2 123.8(2) . . ?
C9 C8 O2 112.46(19) . . ?
C9 C8 O3 123.7(2) . . ?
C8 C9 N1 110.65(18) . . ?
H9 C9 N1 108.68(11) . . ?
H9 C9 C8 108.68(12) . . ?
C10 C9 N1 110.76(18) . . ?
C10 C9 C8 109.33(18) . . ?
C10 C9 H9 108.68(12) . . ?
H10a C10 C9 108.73(12) . . ?
H10b C10 C9 108.73(12) . . ?
H10b C10 H10a 107.6 . . ?
C11 C10 C9 114.08(18) . . ?
C11 C10 H10a 108.73(13) . . ?
C11 C10 H10b 108.73(12) . . ?
H11 C11 C10 108.79(13) . . ?
C12 C11 C10 110.4(2) . . ?
C12 C11 H11 108.79(15) . . ?
C13 C11 C10 110.6(2) . . ?
C13 C11 H11 108.79(15) . . ?
C13 C11 C12 109.5(2) . . ?
H12a C12 C11 109.5 . . ?
H12b C12 C11 109.5 . . ?
H12b C12 H12a 109.5 . . ?
H12c C12 C11 109.5 . . ?
H12c C12 H12a 109.5 . . ?
H12c C12 H12b 109.5 . . ?
H13a C13 C11 109.5 . . ?
H13b C13 C11 109.5 . . ?
H13b C13 H13a 109.5 . . ?
H13c C13 C11 109.5 . . ?
H13c C13 H13a 109.5 . . ?
H13c C13 H13b 109.5 . . ?
H14a C14 C5 109.5 . . ?
H14b C14 C5 109.5 . . ?
H14b C14 H14a 109.5 . . ?
H14c C14 C5 109.5 . . ?
H14c C14 H14a 109.5 . . ?
H14c C14 H14b 109.5 . . ?

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
O2 H2 O3 0.91(3) 1.74(3) 2.641(2) 172(3) 3_656
N1 H1 O1 0.81(3) 2.15(3) 2.942(2) 166(2) 4_565

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 N1 C9 6.1(3) . . . . ?
O1 C1 C2 C3 -10.6(2) . . . . ?
O1 C1 C2 C7 169.4(2) . . . . ?
O2 C8 C9 N1 -160.44(18) . . . . ?
O2 C8 C9 C10 77.3(2) . . . . ?
O3 C8 C9 N1 21.9(2) . . . . ?
O3 C8 C9 C10 -100.3(2) . . . . ?
N1 C1 C2 C3 169.3(2) . . . . ?
N1 C1 C2 C7 -10.7(2) . . . . ?
N1 C9 C10 C11 73.3(2) . . . . ?
C1 C2 C3 C4 -178.0(2) . . . . ?
C1 C2 C7 C6 178.9(2) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C2 C7 C6 C5 -1.2(3) . . . . ?
C3 C4 C5 C6 -1.8(3) . . . . ?
C3 C4 C5 C14 178.3(2) . . . . ?
C4 C5 C6 C7 2.7(3) . . . . ?
C8 C9 C10 C11 -164.52(18) . . . . ?
C9 C10 C11 C12 74.7(2) . . . . ?
C9 C10 C11 C13 -164.1(2) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
####################################################################### 
# 
# 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_21kaw55_a
_database_code_depnum_ccdc_archive 'CCDC 2312801'
loop_
_audit_author_name
_audit_author_address
'Kraig Wheeler'
;Whitworth University
United States of America
;
_audit_update_record             
;
2023-12-18 deposited with the CCDC.	2024-02-12 downloaded from the CCDC.
;
_audit_creation_date             2023-12-14
_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         'C17 H17 N O3'
_chemical_formula_sum            'C17 H17 N O3'
_chemical_formula_weight         283.31
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.8048(5)
_cell_length_b                   10.1624(5)
_cell_length_c                   14.3028(6)
_cell_angle_alpha                90
_cell_angle_beta                 110.088(2)
_cell_angle_gamma                90
_cell_volume                     1474.95(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9938
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.01
_cell_measurement_theta_min      4.36
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.712
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.213
_exptl_crystal_size_mid          0.179
_exptl_crystal_size_min          0.071
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0124
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            33896
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.136
_diffrn_reflns_theta_min         5.458
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'κ-geometry four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'focusing mirror'
_diffrn_radiation_detector       'Bruker PHOTON II'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2782
_reflns_number_total             2907
_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       'SAINT+ V8.40B (Bruker AXS Inc., 2020)'
_computing_data_collection       'APEX5 Ver.2022.08-RC130 (Bruker-AXS, 2023)'
_computing_data_reduction        'SAINT+ Ve8.40B (Bruker-AXS, 2020)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2019/1)'
_computing_structure_solution    'XT (Sheldrick, 2018/2)'
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         2907
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0327
_refine_ls_restrained_S_all      1.047
_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)+(0.0336P)²+0.6406P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0795
_refine_ls_wR_factor_ref         0.0806
_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron density map and refined using anisotropic displacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv of the connected C atoms (1.5xUeqiv for methyl groups). Those H atoms
 attached to nitrogen and oxygen were located in Fourier diff maps and assigned Uiso = 1.2xUeqiv for nitrogen (1.5xUeqiv for oxygen).
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_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 0.34612(7) 0.78119(7) 0.33349(5) 0.01905(17) Uani 1 1 d . . . . .
O2 O 0.17111(7) 0.45562(8) 0.30242(6) 0.02201(18) Uani 1 1 d . . . . .
H2 H 0.1725(13) 0.3975(14) 0.2547(11) 0.026 Uiso 1 1 d . U . . .
O3 O 0.39195(7) 0.45714(7) 0.34862(5) 0.01823(17) Uani 1 1 d . . . . .
N1 N 0.40127(8) 0.66819(8) 0.47612(6) 0.01576(19) Uani 1 1 d . . . . .
H1 H 0.4640(13) 0.6432(13) 0.5320(10) 0.019 Uiso 1 1 d . U . . .
C1 C 0.42558(10) 0.76260(10) 0.41925(7) 0.0149(2) Uani 1 1 d . . . . .
C2 C 0.54934(10) 0.84009(10) 0.46327(7) 0.0153(2) Uani 1 1 d . . . . .
C3 C 0.59551(10) 0.91697(11) 0.40152(8) 0.0191(2) Uani 1 1 d . . . . .
H3 H 0.547780 0.919642 0.332027 0.023 Uiso 1 1 calc R U . . .
C4 C 0.71072(10) 0.98975(11) 0.44064(8) 0.0212(2) Uani 1 1 d . . . . .
H4 H 0.740387 1.042215 0.397551 0.025 Uiso 1 1 calc R U . . .
C5 C 0.78332(10) 0.98691(10) 0.54210(8) 0.0183(2) Uani 1 1 d . . . . .
C6 C 0.73702(10) 0.90944(10) 0.60370(7) 0.0184(2) Uani 1 1 d . . . . .
H6 H 0.785833 0.905463 0.672974 0.022 Uiso 1 1 calc R U . . .
C7 C 0.62124(10) 0.83833(10) 0.56560(7) 0.0174(2) Uani 1 1 d . . . . .
H7 H 0.590311 0.788011 0.609071 0.021 Uiso 1 1 calc R U . . .
C8 C 0.28996(10) 0.49379(10) 0.35822(7) 0.0157(2) Uani 1 1 d . . . . .
C9 C 0.28307(10) 0.58860(10) 0.43905(7) 0.0164(2) Uani 1 1 d . . . . .
H9 H 0.205889 0.648399 0.409803 0.020 Uiso 1 1 calc R U . . .
C10 C 0.26297(10) 0.51162(10) 0.52548(8) 0.0182(2) Uani 1 1 d . . . . .
H10A H 0.191670 0.446287 0.498191 0.022 Uiso 1 1 calc R U . . .
H10B H 0.344823 0.463178 0.561999 0.022 Uiso 1 1 calc R U . . .
C11 C 0.22785(11) 0.60152(10) 0.59699(8) 0.0196(2) Uani 1 1 d . . . . .
C12 C 0.09821(11) 0.64413(11) 0.57508(9) 0.0241(2) Uani 1 1 d . . . . .
H12 H 0.032018 0.615137 0.515685 0.029 Uiso 1 1 calc R U . . .
C13 C 0.06464(12) 0.72873(12) 0.63929(10) 0.0290(3) Uani 1 1 d . . . . .
H13 H -0.024124 0.756406 0.623966 0.035 Uiso 1 1 calc R U . . .
C14 C 0.16083(14) 0.77230(12) 0.72536(9) 0.0310(3) Uani 1 1 d . . . . .
H14 H 0.138423 0.830198 0.769213 0.037 Uiso 1 1 calc R U . . .
C15 C 0.29004(13) 0.73114(13) 0.74739(9) 0.0316(3) Uani 1 1 d . . . . .
H15 H 0.356243 0.761390 0.806329 0.038 Uiso 1 1 calc R U . . .
C16 C 0.32338(12) 0.64596(12) 0.68385(8) 0.0259(3) Uani 1 1 d . . . . .
H16 H 0.412134 0.617880 0.699886 0.031 Uiso 1 1 calc R U . . .
C17 C 0.90741(11) 1.06655(11) 0.58601(8) 0.0238(2) Uani 1 1 d . . . . .
H17A H 0.920966 1.121476 0.534034 0.036 Uiso 1 1 calc R U . . .
H17B H 0.982697 1.007151 0.613319 0.036 Uiso 1 1 calc R U . . .
H17C H 0.899308 1.122845 0.639240 0.036 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 1.2465(12) . ?
O2 H2 0.906(15) . ?
O2 C8 1.3162(12) . ?
O3 C8 1.2148(13) . ?
N1 H1 0.889(14) . ?
N1 C1 1.3409(13) . ?
N1 C9 1.4495(13) . ?
C1 C2 1.4921(14) . ?
C2 C3 1.3935(14) . ?
C2 C7 1.4018(14) . ?
C3 H3 0.9500 . ?
C3 C4 1.3897(15) . ?
C4 H4 0.9500 . ?
C4 C5 1.3929(15) . ?
C5 C6 1.3960(15) . ?
C5 C17 1.5063(14) . ?
C6 H6 0.9500 . ?
C6 C7 1.3842(15) . ?
C7 H7 0.9500 . ?
C8 C9 1.5263(14) . ?
C9 H9 1.0000 . ?
C9 C10 1.5400(14) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5137(14) . ?
C11 C12 1.3951(15) . ?
C11 C16 1.3900(16) . ?
C12 H12 0.9500 . ?
C12 C13 1.3940(17) . ?
C13 H13 0.9500 . ?
C13 C14 1.3830(19) . ?
C14 H14 0.9500 . ?
C14 C15 1.3861(19) . ?
C15 H15 0.9500 . ?
C15 C16 1.3892(16) . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O2 H2 112.6(9) . . ?
C1 N1 H1 120.1(8) . . ?
C1 N1 C9 120.59(8) . . ?
C9 N1 H1 118.3(8) . . ?
O1 C1 N1 119.54(9) . . ?
O1 C1 C2 123.35(9) . . ?
N1 C1 C2 117.11(9) . . ?
C3 C2 C1 119.51(9) . . ?
C3 C2 C7 118.57(9) . . ?
C7 C2 C1 121.92(9) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.62(9) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 120.96(10) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 118.27(10) . . ?
C4 C5 C17 121.69(10) . . ?
C6 C5 C17 120.03(9) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.15(9) . . ?
C7 C6 H6 119.4 . . ?
C2 C7 H7 119.8 . . ?
C6 C7 C2 120.41(9) . . ?
C6 C7 H7 119.8 . . ?
O2 C8 C9 110.74(8) . . ?
O3 C8 O2 125.10(9) . . ?
O3 C8 C9 124.14(9) . . ?
N1 C9 C8 111.30(8) . . ?
N1 C9 H9 108.5 . . ?
N1 C9 C10 109.83(8) . . ?
C8 C9 H9 108.5 . . ?
C8 C9 C10 110.14(8) . . ?
C10 C9 H9 108.5 . . ?
C9 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 C9 111.90(8) . . ?
C11 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
C12 C11 C10 120.06(10) . . ?
C16 C11 C10 121.23(10) . . ?
C16 C11 C12 118.69(10) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.78(11) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.86(11) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.74(11) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.43(12) . . ?
C16 C15 H15 119.8 . . ?
C11 C16 H16 119.8 . . ?
C15 C16 C11 120.49(11) . . ?
C15 C16 H16 119.8 . . ?
C5 C17 H17A 109.5 . . ?
C5 C17 H17B 109.5 . . ?
C5 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
O2 H2 O1 0.906(15) 1.690(15) 2.5899(10) 171.7(13) 2_545 yes
N1 H1 O3 0.889(14) 2.134(14) 3.0084(11) 167.7(12) 3_666 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
O1 C1 C2 C3 -14.49(15) . . . . ?
O1 C1 C2 C7 165.39(10) . . . . ?
O2 C8 C9 N1 -158.58(8) . . . . ?
O2 C8 C9 C10 79.36(10) . . . . ?
O3 C8 C9 N1 22.80(14) . . . . ?
O3 C8 C9 C10 -99.27(11) . . . . ?
N1 C1 C2 C3 165.07(9) . . . . ?
N1 C1 C2 C7 -15.05(14) . . . . ?
N1 C9 C10 C11 68.73(11) . . . . ?
C1 N1 C9 C8 70.83(11) . . . . ?
C1 N1 C9 C10 -166.93(9) . . . . ?
C1 C2 C3 C4 -179.82(9) . . . . ?
C1 C2 C7 C6 178.77(9) . . . . ?
C2 C3 C4 C5 0.53(16) . . . . ?
C3 C2 C7 C6 -1.35(15) . . . . ?
C3 C4 C5 C6 -0.30(16) . . . . ?
C3 C4 C5 C17 -179.17(10) . . . . ?
C4 C5 C6 C7 -0.76(15) . . . . ?
C5 C6 C7 C2 1.61(16) . . . . ?
C7 C2 C3 C4 0.30(15) . . . . ?
C8 C9 C10 C11 -168.34(8) . . . . ?
C9 N1 C1 O1 -0.55(14) . . . . ?
C9 N1 C1 C2 179.87(8) . . . . ?
C9 C10 C11 C12 81.60(12) . . . . ?
C9 C10 C11 C16 -96.72(12) . . . . ?
C10 C11 C12 C13 -178.89(10) . . . . ?
C10 C11 C16 C15 178.33(10) . . . . ?
C11 C12 C13 C14 0.64(17) . . . . ?
C12 C11 C16 C15 -0.01(17) . . . . ?
C12 C13 C14 C15 -0.21(18) . . . . ?
C13 C14 C15 C16 -0.32(19) . . . . ?
C14 C15 C16 C11 0.44(19) . . . . ?
C16 C11 C12 C13 -0.53(16) . . . . ?
C17 C5 C6 C7 178.12(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
####################################################################### 
# 
# 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_22kaw09_a
_database_code_depnum_ccdc_archive 'CCDC 2312800'
loop_
_audit_author_name
_audit_author_address
'Kraig Wheeler'
;Whitworth University
United States of America
;
_audit_update_record             
;
2023-12-18 deposited with the CCDC.	2024-02-12 downloaded from the CCDC.
;
_audit_creation_date             2023-12-14
_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         'C13 H16 Cl N O3'
_chemical_formula_sum            'C13 H16 Cl N O3'
_chemical_formula_weight         269.72
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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                   8.5014(4)
_cell_length_b                   16.7568(8)
_cell_length_c                   10.0698(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.680(3)
_cell_angle_gamma                90
_cell_volume                     1381.12(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7898
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.24
_cell_measurement_theta_min      5.27
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.463
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5559
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.237
_exptl_crystal_size_mid          0.037
_exptl_crystal_size_min          0.032
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0793
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            17953
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.239
_diffrn_reflns_theta_min         5.271
_diffrn_ambient_temperature      100.00
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'κ-geometry four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'focusing mirror'
_diffrn_radiation_detector       'Bruker PHOTON II'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1936
_reflns_number_total             2515
_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       'SAINT+ V8.40B (Bruker AXS Inc., 2020)'
_computing_data_collection       'APEX5 Ver.2022.08-RC130 (Bruker-AXS, 2023)'
_computing_data_reduction        'SAINT+ Ve8.40B (Bruker-AXS, 2020)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2019/1)'
_computing_structure_solution    'XT (Sheldrick, 2018/2)'
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         2515
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0607
_refine_ls_restrained_S_all      1.065
_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)+(0.0610P)²+1.7607P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1428
_refine_ls_wR_factor_ref         0.1570
_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron density map and refined using anisotropic displacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv of the connected C atoms (1.5xUeqiv for methyl groups). Those H atoms
 attached to nitrogen and oxygen were located in Fourier diff maps and assigned Uiso = 1.2xUeqiv for nitrogen (1.5xUequiv for oxygen).
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_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
Cl1 Cl 0.14619(10) 0.54674(6) 0.41018(11) 0.0576(3) Uani 1 1 d . . . . .
O1 O 0.6088(3) 0.23468(14) 0.6907(2) 0.0410(5) Uani 1 1 d . . . . .
O2 O 0.7092(3) 0.02678(15) 0.5883(3) 0.0507(6) Uani 1 1 d . . . . .
H2 H 0.627(5) -0.011(3) 0.563(4) 0.061 Uiso 1 1 d . U . . .
O3 O 0.4981(3) 0.09213(13) 0.4506(2) 0.0440(6) Uani 1 1 d . . . . .
N1 N 0.6695(3) 0.23256(16) 0.4880(3) 0.0340(6) Uani 1 1 d . . . . .
H1 H 0.641(4) 0.246(2) 0.410(4) 0.041 Uiso 1 1 d . U . . .
C1 C 0.5911(4) 0.26437(19) 0.5757(3) 0.0346(7) Uani 1 1 d . . . . .
C2 C 0.4838(4) 0.33504(18) 0.5298(3) 0.0323(7) Uani 1 1 d . . . . .
C3 C 0.3927(4) 0.3625(2) 0.6165(3) 0.0396(7) Uani 1 1 d . . . . .
H3 H 0.401973 0.336316 0.701938 0.048 Uiso 1 1 calc R U . . .
C4 C 0.2887(4) 0.4273(2) 0.5803(4) 0.0453(8) Uani 1 1 d . . . . .
H4 H 0.226841 0.445424 0.640107 0.054 Uiso 1 1 calc R U . . .
C5 C 0.2761(4) 0.4654(2) 0.4562(4) 0.0440(8) Uani 1 1 d . . . . .
C6 C 0.3660(4) 0.4398(2) 0.3683(3) 0.0435(8) Uani 1 1 d . . . . .
H6 H 0.356634 0.466401 0.283181 0.052 Uiso 1 1 calc R U . . .
C7 C 0.4699(4) 0.3751(2) 0.4060(3) 0.0400(7) Uani 1 1 d . . . . .
H7 H 0.532536 0.357674 0.346308 0.048 Uiso 1 1 calc R U . . .
C8 C 0.6401(4) 0.08976(19) 0.5173(3) 0.0360(7) Uani 1 1 d . . . . .
C9 C 0.7579(4) 0.15791(18) 0.5241(3) 0.0353(7) Uani 1 1 d . . . . .
H9 H 0.829886 0.162102 0.620472 0.042 Uiso 1 1 calc R U . . .
C10 C 0.8650(4) 0.1411(2) 0.4262(3) 0.0371(7) Uani 1 1 d . . . . .
H10A H 0.895246 0.083887 0.432995 0.045 Uiso 1 1 calc R U . . .
H10B H 0.799840 0.151426 0.330324 0.045 Uiso 1 1 calc R U . . .
C11 C 1.0201(4) 0.1908(2) 0.4556(3) 0.0403(7) Uani 1 1 d . . . . .
H11 H 0.992911 0.247127 0.473586 0.048 Uiso 1 1 calc R U . . .
C12 C 1.0922(5) 0.1896(3) 0.3313(4) 0.0530(9) Uani 1 1 d . . . . .
H12A H 1.119495 0.134646 0.312925 0.079 Uiso 1 1 calc R U . . .
H12B H 1.191189 0.222484 0.351548 0.079 Uiso 1 1 calc R U . . .
H12C H 1.011881 0.211014 0.250216 0.079 Uiso 1 1 calc R U . . .
C13 C 1.1479(4) 0.1595(2) 0.5816(4) 0.0518(9) Uani 1 1 d . . . . .
H13A H 1.102504 0.159296 0.661281 0.078 Uiso 1 1 calc R U . . .
H13B H 1.244429 0.194093 0.600950 0.078 Uiso 1 1 calc R U . . .
H13C H 1.178986 0.105115 0.563566 0.078 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
Cl1 C5 1.737(4) . ?
O1 C1 1.232(4) . ?
O2 H2 0.92(4) . ?
O2 C8 1.320(4) . ?
O3 C8 1.213(4) . ?
N1 H1 0.79(4) . ?
N1 C1 1.351(4) . ?
N1 C9 1.454(4) . ?
C1 C2 1.490(4) . ?
C2 C3 1.392(4) . ?
C2 C7 1.393(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.381(5) . ?
C5 C6 1.384(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.386(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.508(4) . ?
C9 H9 1.0000 . ?
C9 C10 1.538(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.520(4) . ?
C11 H11 1.0000 . ?
C11 C12 1.535(4) . ?
C11 C13 1.522(5) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O2 H2 102(3) . . ?
C1 N1 H1 118(3) . . ?
C1 N1 C9 119.2(3) . . ?
C9 N1 H1 120(3) . . ?
O1 C1 N1 119.9(3) . . ?
O1 C1 C2 121.4(3) . . ?
N1 C1 C2 118.7(3) . . ?
C3 C2 C1 117.8(3) . . ?
C3 C2 C7 118.4(3) . . ?
C7 C2 C1 123.9(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.2(3) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.2(3) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 Cl1 119.4(3) . . ?
C4 C5 C6 121.0(3) . . ?
C6 C5 Cl1 119.6(3) . . ?
C5 C6 H6 120.4 . . ?
C5 C6 C7 119.2(3) . . ?
C7 C6 H6 120.4 . . ?
C2 C7 H7 119.5 . . ?
C6 C7 C2 121.1(3) . . ?
C6 C7 H7 119.5 . . ?
O2 C8 C9 112.8(3) . . ?
O3 C8 O2 123.8(3) . . ?
O3 C8 C9 123.3(3) . . ?
N1 C9 C8 110.4(2) . . ?
N1 C9 H9 108.8 . . ?
N1 C9 C10 110.7(3) . . ?
C8 C9 H9 108.8 . . ?
C8 C9 C10 109.4(2) . . ?
C10 C9 H9 108.8 . . ?
C9 C10 H10A 108.7 . . ?
C9 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C11 C10 C9 114.0(3) . . ?
C11 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C10 C11 H11 108.8 . . ?
C10 C11 C12 110.5(3) . . ?
C10 C11 C13 111.1(3) . . ?
C12 C11 H11 108.8 . . ?
C13 C11 H11 108.8 . . ?
C13 C11 C12 108.8(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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
O2 H2 O3 0.92(4) 1.71(4) 2.619(3) 167(4) 3_656 yes
N1 H1 O1 0.79(4) 2.17(4) 2.948(3) 167(4) 4_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
Cl1 C5 C6 C7 179.7(3) . . . . ?
O1 C1 C2 C3 -5.4(4) . . . . ?
O1 C1 C2 C7 174.5(3) . . . . ?
O2 C8 C9 N1 -160.1(3) . . . . ?
O2 C8 C9 C10 77.9(3) . . . . ?
O3 C8 C9 N1 21.7(4) . . . . ?
O3 C8 C9 C10 -100.3(4) . . . . ?
N1 C1 C2 C3 174.3(3) . . . . ?
N1 C1 C2 C7 -5.8(4) . . . . ?
N1 C9 C10 C11 76.2(3) . . . . ?
C1 N1 C9 C8 70.0(3) . . . . ?
C1 N1 C9 C10 -168.7(3) . . . . ?
C1 C2 C3 C4 -179.3(3) . . . . ?
C1 C2 C7 C6 179.1(3) . . . . ?
C2 C3 C4 C5 -0.2(5) . . . . ?
C3 C2 C7 C6 -1.0(5) . . . . ?
C3 C4 C5 Cl1 -179.9(3) . . . . ?
C3 C4 C5 C6 -0.3(5) . . . . ?
C4 C5 C6 C7 0.1(5) . . . . ?
C5 C6 C7 C2 0.6(5) . . . . ?
C7 C2 C3 C4 0.9(5) . . . . ?
C8 C9 C10 C11 -162.0(3) . . . . ?
C9 N1 C1 O1 7.4(4) . . . . ?
C9 N1 C1 C2 -172.3(2) . . . . ?
C9 C10 C11 C12 -163.0(3) . . . . ?
C9 C10 C11 C13 76.1(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
####################################################################### 
# 
# 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_21kaw70_a
_database_code_depnum_ccdc_archive 'CCDC 2312802'
loop_
_audit_author_name
_audit_author_address
'Kraig Wheeler'
;Whitworth University
United States of America
;
_audit_update_record             
;
2023-12-08 deposited with the CCDC.	2024-02-12 downloaded from the CCDC.
;
_audit_creation_date             2023-11-15
_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         'C16 H14 Cl N O3'
_chemical_formula_sum            'C16 H14 Cl N O3'
_chemical_formula_weight         303.73
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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                   10.9337(3)
_cell_length_b                   9.8520(3)
_cell_length_c                   14.5888(5)
_cell_angle_alpha                90
_cell_angle_beta                 111.998(2)
_cell_angle_gamma                90
_cell_volume                     1457.08(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9889
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.14
_cell_measurement_theta_min      4.36
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.408
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6373
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.185
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.019
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            27695
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.186
_diffrn_reflns_theta_min         4.361
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'κ-geometry four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'focusing mirror'
_diffrn_radiation_detector       'Bruker PHOTON II'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2572
_reflns_number_total             2870
_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       'SAINT+ V8.40B (Bruker AXS Inc., 2020)'
_computing_data_collection       'APEX5 Ver.2022.08-RC130 (Bruker-AXS, 2023)'
_computing_data_reduction        'SAINT+ Ve8.40B (Bruker-AXS, 2020)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2019/1)'
_computing_structure_solution    'XT (Sheldrick, 2018/2)'
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2870
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0284
_refine_ls_restrained_S_all      1.059
_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)+(0.0264P)²+0.7489P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0670
_refine_ls_wR_factor_ref         0.0695
_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron density map and refined using anisotropic displacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv of the connected C atoms. Those H atoms attached to nitrogen and oxygen were located in Fourier diff maps and assigned Uiso = 1.2xUeqiv for nitrogen (1.5xUeqiv for oxygen).
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
Cl1 Cl 0.15556(3) 1.07662(3) 0.59124(2) 0.02547(10) Uani 1 1 d . . . . .
O1 O 0.47907(9) 0.77927(9) 0.33166(6) 0.0206(2) Uani 1 1 d . . . . .
O2 O 0.63928(9) 0.46081(11) 0.30170(7) 0.0243(2) Uani 1 1 d . . . . .
H2 H 0.5987(17) 0.4054(19) 0.2601(13) 0.029 Uiso 1 1 d . U . . .
O3 O 0.46983(9) 0.45095(9) 0.35281(7) 0.0195(2) Uani 1 1 d . . . . .
N1 N 0.57380(10) 0.67212(11) 0.47660(8) 0.0168(2) Uani 1 1 d . . . . .
H1 H 0.5675(15) 0.6477(16) 0.5299(12) 0.020 Uiso 1 1 d . U . . .
C1 C 0.48801(12) 0.76246(13) 0.41845(9) 0.0165(3) Uani 1 1 d . . . . .
C2 C 0.40652(12) 0.83976(13) 0.46315(9) 0.0164(3) Uani 1 1 d . . . . .
C3 C 0.29145(13) 0.90337(14) 0.40101(10) 0.0205(3) Uani 1 1 d . . . . .
H3 H 0.266245 0.896545 0.331385 0.025 Uiso 1 1 calc R U . . .
C4 C 0.21315(13) 0.97658(15) 0.43951(10) 0.0226(3) Uani 1 1 d . . . . .
H4 H 0.134875 1.019958 0.396952 0.027 Uiso 1 1 calc R U . . .
C5 C 0.25150(13) 0.98506(13) 0.54126(10) 0.0194(3) Uani 1 1 d . . . . .
C6 C 0.36517(13) 0.92241(13) 0.60485(10) 0.0201(3) Uani 1 1 d . . . . .
H6 H 0.389312 0.928538 0.674414 0.024 Uiso 1 1 calc R U . . .
C7 C 0.44307(13) 0.85071(13) 0.56546(10) 0.0190(3) Uani 1 1 d . . . . .
H7 H 0.521944 0.808685 0.608365 0.023 Uiso 1 1 calc R U . . .
C8 C 0.57675(12) 0.49447(13) 0.35971(9) 0.0171(3) Uani 1 1 d . . . . .
C9 C 0.65792(12) 0.59392(13) 0.43964(9) 0.0169(3) Uani 1 1 d . . . . .
H9 H 0.704546 0.657708 0.410377 0.020 Uiso 1 1 calc R U . . .
C10 C 0.76165(12) 0.51657(13) 0.52558(10) 0.0193(3) Uani 1 1 d . . . . .
H10A H 0.716578 0.464924 0.561996 0.023 Uiso 1 1 calc R U . . .
H10B H 0.807641 0.450676 0.498449 0.023 Uiso 1 1 calc R U . . .
C11 C 0.86210(13) 0.61074(13) 0.59649(10) 0.0203(3) Uani 1 1 d . . . . .
C12 C 0.84562(14) 0.66195(15) 0.67975(10) 0.0260(3) Uani 1 1 d . . . . .
H12 H 0.771092 0.635742 0.694105 0.031 Uiso 1 1 calc R U . . .
C13 C 0.93798(16) 0.75176(16) 0.74249(11) 0.0316(3) Uani 1 1 d . . . . .
H13 H 0.925433 0.787228 0.798894 0.038 Uiso 1 1 calc R U . . .
C14 C 1.04742(15) 0.78930(15) 0.72303(11) 0.0324(4) Uani 1 1 d . . . . .
H14 H 1.110253 0.850104 0.766123 0.039 Uiso 1 1 calc R U . . .
C15 C 1.06546(14) 0.73837(15) 0.64083(12) 0.0316(3) Uani 1 1 d . . . . .
H15 H 1.141137 0.763425 0.627601 0.038 Uiso 1 1 calc R U . . .
C16 C 0.97284(13) 0.65046(14) 0.57753(12) 0.0262(3) Uani 1 1 d . . . . .
H16 H 0.985043 0.616896 0.520498 0.031 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
Cl1 C5 1.7375(13) . ?
O1 C1 1.2440(15) . ?
O2 H2 0.813(19) . ?
O2 C8 1.3142(15) . ?
O3 C8 1.2135(16) . ?
N1 H1 0.841(17) . ?
N1 C1 1.3400(17) . ?
N1 C9 1.4497(16) . ?
C1 C2 1.4947(18) . ?
C2 C3 1.3939(18) . ?
C2 C7 1.3972(18) . ?
C3 H3 0.9500 . ?
C3 C4 1.3889(19) . ?
C4 H4 0.9500 . ?
C4 C5 1.3855(19) . ?
C5 C6 1.3866(19) . ?
C6 H6 0.9500 . ?
C6 C7 1.3862(19) . ?
C7 H7 0.9500 . ?
C8 C9 1.5271(17) . ?
C9 H9 1.0000 . ?
C9 C10 1.5407(17) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5119(18) . ?
C11 C12 1.388(2) . ?
C11 C16 1.3952(19) . ?
C12 H12 0.9500 . ?
C12 C13 1.396(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.380(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.381(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.388(2) . ?
C16 H16 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
C8 O2 H2 112.3(12) . . ?
C1 N1 H1 119.6(11) . . ?
C1 N1 C9 120.58(11) . . ?
C9 N1 H1 118.4(11) . . ?
O1 C1 N1 120.15(12) . . ?
O1 C1 C2 122.94(11) . . ?
N1 C1 C2 116.91(11) . . ?
C3 C2 C1 119.05(11) . . ?
C3 C2 C7 119.17(12) . . ?
C7 C2 C1 121.78(11) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.89(12) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 120.7 . . ?
C5 C4 C3 118.66(12) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 Cl1 119.53(10) . . ?
C4 C5 C6 121.72(12) . . ?
C6 C5 Cl1 118.75(10) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 C5 119.04(12) . . ?
C7 C6 H6 120.5 . . ?
C2 C7 H7 119.7 . . ?
C6 C7 C2 120.53(12) . . ?
C6 C7 H7 119.7 . . ?
O2 C8 C9 111.09(10) . . ?
O3 C8 O2 125.10(12) . . ?
O3 C8 C9 123.80(11) . . ?
N1 C9 C8 110.90(10) . . ?
N1 C9 H9 108.7 . . ?
N1 C9 C10 109.65(10) . . ?
C8 C9 H9 108.7 . . ?
C8 C9 C10 110.13(10) . . ?
C10 C9 H9 108.7 . . ?
C9 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 C9 112.21(11) . . ?
C11 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
C12 C11 C10 121.51(12) . . ?
C12 C11 C16 118.57(13) . . ?
C16 C11 C10 119.90(13) . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.35(14) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.34(15) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.90(14) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 119.90(14) . . ?
C16 C15 H15 120.0 . . ?
C11 C16 H16 119.5 . . ?
C15 C16 C11 120.93(14) . . ?
C15 C16 H16 119.5 . . ?

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
O2 H2 O1 0.813(19) 1.791(19) 2.6024(13) 175.7(18) 2_645 yes
N1 H1 O3 0.841(17) 2.136(17) 2.9632(14) 167.7(15) 3_666 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
Cl1 C5 C6 C7 -179.16(10) . . . . ?
O1 C1 C2 C3 19.03(18) . . . . ?
O1 C1 C2 C7 -160.53(12) . . . . ?
O2 C8 C9 N1 156.74(11) . . . . ?
O2 C8 C9 C10 -81.70(13) . . . . ?
O3 C8 C9 N1 -24.65(17) . . . . ?
O3 C8 C9 C10 96.91(14) . . . . ?
N1 C1 C2 C3 -161.18(12) . . . . ?
N1 C1 C2 C7 19.27(17) . . . . ?
N1 C9 C10 C11 -69.30(13) . . . . ?
C1 N1 C9 C8 -67.52(15) . . . . ?
C1 N1 C9 C10 170.64(11) . . . . ?
C1 C2 C3 C4 -179.79(12) . . . . ?
C1 C2 C7 C6 -179.62(12) . . . . ?
C2 C3 C4 C5 -0.1(2) . . . . ?
C3 C2 C7 C6 0.82(19) . . . . ?
C3 C4 C5 Cl1 179.75(10) . . . . ?
C3 C4 C5 C6 -0.1(2) . . . . ?
C4 C5 C6 C7 0.7(2) . . . . ?
C5 C6 C7 C2 -1.1(2) . . . . ?
C7 C2 C3 C4 -0.2(2) . . . . ?
C8 C9 C10 C11 168.40(10) . . . . ?
C9 N1 C1 O1 0.57(18) . . . . ?
C9 N1 C1 C2 -179.23(11) . . . . ?
C9 C10 C11 C12 92.73(15) . . . . ?
C9 C10 C11 C16 -85.74(15) . . . . ?
C10 C11 C12 C13 -178.17(13) . . . . ?
C10 C11 C16 C15 179.08(13) . . . . ?
C11 C12 C13 C14 -0.8(2) . . . . ?
C12 C11 C16 C15 0.6(2) . . . . ?
C12 C13 C14 C15 0.3(2) . . . . ?
C13 C14 C15 C16 0.6(2) . . . . ?
C14 C15 C16 C11 -1.0(2) . . . . ?
C16 C11 C12 C13 0.3(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
####################################################################### 
# 
# 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_23kaw78
_database_code_depnum_ccdc_archive 'CCDC 2312803'
loop_
_audit_author_name
_audit_author_address
'Kraig Wheeler'
;Whitworth University
United States of America
;
_audit_update_record             
;
2024-01-24 deposited with the CCDC.	2024-02-12 downloaded from the CCDC.
;
_audit_creation_date             2023-12-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H19 N O3, C13 H16 Cl N O3'
_chemical_formula_sum            'C27 H35 Cl N2 O6'
_chemical_formula_weight         519.02
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.5052(3)
_cell_length_b                   16.9899(7)
_cell_length_c                   10.0551(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.507(2)
_cell_angle_gamma                90
_cell_volume                     1385.68(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9986
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.23
_cell_measurement_theta_min      4.61
_shelx_estimated_absorpt_T_max   0.937
_shelx_estimated_absorpt_T_min   0.584
_exptl_absorpt_coefficient_mu    1.567
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6029
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.385
_exptl_crystal_size_mid          0.068
_exptl_crystal_size_min          0.042
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            24521
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.339
_diffrn_reflns_theta_min         4.611
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'κ-geometry four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'focusing mirror'
_diffrn_radiation_detector       'Bruker PHOTON II'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.919
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                4819
_reflns_number_total             5045
_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       'SAINT+ V8.40B (Bruker AXS Inc., 2020)'
_computing_data_collection       'APEX5 Ver.2022.08-RC130 (Bruker-AXS, 2023)'
_computing_data_reduction        'SAINT+ Ve8.40B (Bruker-AXS, 2020)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2019/1)'
_computing_structure_solution    'XT (Sheldrick, 2018/2)'
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 2169 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.108(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     342
_refine_ls_number_reflns         5045
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0354
_refine_ls_restrained_S_all      1.046
_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)+(0.0527P)²+0.3613P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.0955
_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier 
electron density map and refined using anisotropic displacement 
parameters. All C-H hydrogen atoms were placed in calculated 
positions with Uiso = 1.2xUeqiv of the connected C atoms 
(1.5xUeqiv for methyl groups). Those H atoms attached to nitrogen 
and oxygen were located in Fourier diff mapsand assigned Uiso = 
1.2xUeqiv for NH groups (Uiso = 1.5xUeqiv for OH groups).
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 N1B-H1B \\sim N1A-H1A \\sim O2B-H2B \\sim O2A-H2A
 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C9A(H9A), C11A(H11A), C9B(H9B), C11B(H11B)
3.b Secondary CH2 refined with riding coordinates:
 C10A(H10A,H10B), C10B(H10C,H10D)
3.c Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C4A(H4A), C6A(H6A), C7A(H7A), C3B(H3B), C4B(H4B), C6B(H6B), C7B(H7B)
3.d Idealised Me refined as rotating group:
 C12A(H12A,H12B,H12C), C13A(H13A,H13B,H13C), C14A(H14A,H14B,H14C), C12B(H12D,
 H12E,H12F), C13B(H13D,H13E,H13F)
;
_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 0.6183(3) 0.23741(13) 0.4456(2) 0.0296(5) Uani 1 1 d . . . . .
O2A O 0.7146(3) 0.03432(13) 0.3395(3) 0.0380(6) Uani 1 1 d D . . . .
H2A H 0.638(5) 0.000(2) 0.314(5) 0.057 Uiso 1 1 d D U . . .
O3A O 0.4978(3) 0.09962(13) 0.2023(2) 0.0326(5) Uani 1 1 d . . . . .
N1A N 0.6738(3) 0.23762(15) 0.2414(3) 0.0240(5) Uani 1 1 d D . . . .
H1A H 0.639(4) 0.252(2) 0.160(3) 0.029 Uiso 1 1 d D U . . .
C1A C 0.5975(4) 0.26791(18) 0.3298(3) 0.0234(6) Uani 1 1 d . . . . .
C2A C 0.4883(4) 0.33779(18) 0.2834(3) 0.0247(6) Uani 1 1 d . . . . .
C3A C 0.3948(4) 0.36311(19) 0.3681(3) 0.0300(7) Uani 1 1 d . . . . .
H3A H 0.404818 0.336909 0.453689 0.036 Uiso 1 1 calc R U . . .
C4A C 0.2882(4) 0.4258(2) 0.3285(3) 0.0345(7) Uani 1 1 d . . . . .
H4A H 0.225412 0.442124 0.387333 0.041 Uiso 1 1 calc R U . . .
C5A C 0.2706(3) 0.4655(2) 0.2044(3) 0.0324(6) Uani 1 1 d . . . . .
C6A C 0.3674(4) 0.4418(2) 0.1228(3) 0.0355(8) Uani 1 1 d . . . . .
H6A H 0.360089 0.469502 0.039101 0.043 Uiso 1 1 calc R U . . .
C7A C 0.4741(4) 0.3788(2) 0.1602(3) 0.0331(7) Uani 1 1 d . . . . .
H7A H 0.538019 0.363272 0.101825 0.040 Uiso 1 1 calc R U . . .
C8A C 0.6429(4) 0.09666(18) 0.2697(3) 0.0262(6) Uani 1 1 d . . . . .
C9A C 0.7622(4) 0.16394(18) 0.2766(3) 0.0254(6) Uani 1 1 d . . . . .
H9A H 0.838864 0.167615 0.373738 0.030 Uiso 1 1 calc R U . . .
C10A C 0.8631(4) 0.14749(19) 0.1767(3) 0.0278(6) Uani 1 1 d . . . . .
H10A H 0.894230 0.091150 0.183574 0.033 Uiso 1 1 calc R U . . .
H10B H 0.792877 0.157408 0.080031 0.033 Uiso 1 1 calc R U . . .
C11A C 1.0198(4) 0.1972(2) 0.2047(3) 0.0320(7) Uani 1 1 d . . . . .
H11A H 0.992702 0.252922 0.221452 0.038 Uiso 1 1 calc R U . . .
C12A C 1.1527(4) 0.1675(2) 0.3327(4) 0.0400(8) Uani 1 1 d . . . . .
H12A H 1.111057 0.168666 0.413572 0.060 Uiso 1 1 calc R U . . .
H12B H 1.250261 0.201238 0.350544 0.060 Uiso 1 1 calc R U . . .
H12C H 1.182324 0.113369 0.316398 0.060 Uiso 1 1 calc R U . . .
C13A C 1.0833(4) 0.1950(3) 0.0783(4) 0.0421(8) Uani 1 1 d . . . . .
H13A H 1.116314 0.141139 0.064119 0.063 Uiso 1 1 calc R U . . .
H13B H 1.178613 0.230122 0.094078 0.063 Uiso 1 1 calc R U . . .
H13C H 0.996006 0.212307 -0.004596 0.063 Uiso 1 1 calc R U . . .
C14A C 0.1505(4) 0.5349(2) 0.1597(4) 0.0438(9) Uani 1 1 d . . . . .
H14A H 0.049661 0.517072 0.089695 0.066 Uiso 1 1 calc R U . . .
H14B H 0.202240 0.576569 0.119853 0.066 Uiso 1 1 calc R U . . .
H14C H 0.123118 0.555468 0.241091 0.066 Uiso 1 1 calc R U . . .
Cl1B Cl 0.84721(11) -0.53153(6) 0.33962(11) 0.0497(2) Uani 1 1 d . . . . .
O1B O 0.3785(3) -0.22257(14) 0.0551(2) 0.0306(5) Uani 1 1 d . . . . .
O2B O 0.2857(3) -0.01712(13) 0.1628(3) 0.0375(6) Uani 1 1 d D . . . .
H2B H 0.354(5) 0.018(2) 0.161(5) 0.056 Uiso 1 1 d D U . . .
O3B O 0.5032(3) -0.08295(13) 0.2973(2) 0.0313(5) Uani 1 1 d . . . . .
N1B N 0.3276(3) -0.22053(15) 0.2612(3) 0.0240(5) Uani 1 1 d D . . . .
H1B H 0.348(4) -0.236(2) 0.342(3) 0.029 Uiso 1 1 d D U . . .
C1B C 0.4003(4) -0.25205(17) 0.1725(3) 0.0236(6) Uani 1 1 d . . . . .
C2B C 0.5067(4) -0.32284(18) 0.2169(3) 0.0243(6) Uani 1 1 d . . . . .
C3B C 0.5983(4) -0.3484(2) 0.1316(3) 0.0305(7) Uani 1 1 d . . . . .
H3B H 0.589197 -0.321193 0.046999 0.037 Uiso 1 1 calc R U . . .
C4B C 0.7026(4) -0.4127(2) 0.1677(3) 0.0364(8) Uani 1 1 d . . . . .
H4B H 0.764969 -0.429517 0.108885 0.044 Uiso 1 1 calc R U . . .
C5B C 0.7145(4) -0.4522(2) 0.2915(3) 0.0340(7) Uani 1 1 d . . . . .
C6B C 0.6217(4) -0.4293(2) 0.3759(3) 0.0340(7) Uani 1 1 d . . . . .
H6B H 0.628382 -0.457743 0.458719 0.041 Uiso 1 1 calc R U . . .
C7B C 0.5191(4) -0.36489(19) 0.3396(3) 0.0309(7) Uani 1 1 d . . . . .
H7B H 0.456103 -0.348820 0.398452 0.037 Uiso 1 1 calc R U . . .
C8B C 0.3578(4) -0.07948(17) 0.2316(3) 0.0246(6) Uani 1 1 d . . . . .
C9B C 0.2385(4) -0.14681(18) 0.2263(3) 0.0262(6) Uani 1 1 d . . . . .
H9B H 0.161511 -0.150762 0.129338 0.031 Uiso 1 1 calc R U . . .
C10B C 0.1376(4) -0.12982(19) 0.3261(3) 0.0268(6) Uani 1 1 d . . . . .
H10C H 0.208570 -0.137797 0.423071 0.032 Uiso 1 1 calc R U . . .
H10D H 0.103037 -0.073932 0.316251 0.032 Uiso 1 1 calc R U . . .
C11B C -0.0156(4) -0.1816(2) 0.3005(3) 0.0325(7) Uani 1 1 d . . . . .
H11B H 0.014730 -0.237160 0.286070 0.039 Uiso 1 1 calc R U . . .
C12B C -0.1500(4) -0.1542(3) 0.1709(4) 0.0438(9) Uani 1 1 d . . . . .
H12D H -0.182467 -0.100246 0.185037 0.066 Uiso 1 1 calc R U . . .
H12E H -0.245823 -0.189020 0.154120 0.066 Uiso 1 1 calc R U . . .
H12F H -0.108008 -0.155687 0.090196 0.066 Uiso 1 1 calc R U . . .
C13B C -0.0802(5) -0.1787(2) 0.4267(4) 0.0425(8) Uani 1 1 d . . . . .
H13D H 0.005288 -0.197686 0.509352 0.064 Uiso 1 1 calc R U . . .
H13E H -0.178190 -0.212076 0.409438 0.064 Uiso 1 1 calc R U . . .
H13F H -0.109070 -0.124310 0.442186 0.064 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
O1A C1A 1.238(4) . ?
O2A H2A 0.85(3) . ?
O2A C8A 1.315(4) . ?
O3A C8A 1.218(4) . ?
N1A H1A 0.82(2) . ?
N1A C1A 1.350(4) . ?
N1A C9A 1.448(4) . ?
C1A C2A 1.493(4) . ?
C2A C3A 1.396(4) . ?
C2A C7A 1.394(5) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.378(5) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.386(5) . ?
C5A C6A 1.385(4) . ?
C5A C14A 1.537(5) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.380(5) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.516(4) . ?
C9A H9A 1.0000 . ?
C9A C10A 1.531(4) . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C10A C11A 1.531(4) . ?
C11A H11A 1.0000 . ?
C11A C12A 1.522(5) . ?
C11A C13A 1.524(5) . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A H12C 0.9800 . ?
C13A H13A 0.9800 . ?
C13A H13B 0.9800 . ?
C13A H13C 0.9800 . ?
C14A H14A 0.9800 . ?
C14A H14B 0.9800 . ?
C14A H14C 0.9800 . ?
Cl1B C5B 1.730(4) . ?
O1B C1B 1.244(4) . ?
O2B H2B 0.84(3) . ?
O2B C8B 1.312(4) . ?
O3B C8B 1.215(4) . ?
N1B H1B 0.82(2) . ?
N1B C1B 1.340(4) . ?
N1B C9B 1.451(4) . ?
C1B C2B 1.490(4) . ?
C2B C3B 1.391(4) . ?
C2B C7B 1.402(4) . ?
C3B H3B 0.9500 . ?
C3B C4B 1.385(5) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.392(5) . ?
C5B C6B 1.377(5) . ?
C6B H6B 0.9500 . ?
C6B C7B 1.379(5) . ?
C7B H7B 0.9500 . ?
C8B C9B 1.519(4) . ?
C9B H9B 1.0000 . ?
C9B C10B 1.532(4) . ?
C10B H10C 0.9900 . ?
C10B H10D 0.9900 . ?
C10B C11B 1.528(4) . ?
C11B H11B 1.0000 . ?
C11B C12B 1.525(5) . ?
C11B C13B 1.528(5) . ?
C12B H12D 0.9800 . ?
C12B H12E 0.9800 . ?
C12B H12F 0.9800 . ?
C13B H13D 0.9800 . ?
C13B H13E 0.9800 . ?
C13B H13F 0.9800 . ?

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
C8A O2A H2A 101(3) . . ?
C1A N1A H1A 116(3) . . ?
C1A N1A C9A 119.0(2) . . ?
C9A N1A H1A 121(3) . . ?
O1A C1A N1A 120.0(3) . . ?
O1A C1A C2A 121.7(3) . . ?
N1A C1A C2A 118.3(3) . . ?
C3A C2A C1A 118.0(3) . . ?
C7A C2A C1A 123.7(3) . . ?
C7A C2A C3A 118.3(3) . . ?
C2A C3A H3A 119.7 . . ?
C4A C3A C2A 120.5(3) . . ?
C4A C3A H3A 119.7 . . ?
C3A C4A H4A 119.4 . . ?
C3A C4A C5A 121.3(3) . . ?
C5A C4A H4A 119.4 . . ?
C4A C5A C14A 121.2(3) . . ?
C6A C5A C4A 118.0(3) . . ?
C6A C5A C14A 120.7(3) . . ?
C5A C6A H6A 119.3 . . ?
C7A C6A C5A 121.5(3) . . ?
C7A C6A H6A 119.3 . . ?
C2A C7A H7A 119.9 . . ?
C6A C7A C2A 120.3(3) . . ?
C6A C7A H7A 119.9 . . ?
O2A C8A C9A 112.7(2) . . ?
O3A C8A O2A 124.1(3) . . ?
O3A C8A C9A 123.2(3) . . ?
N1A C9A C8A 110.5(2) . . ?
N1A C9A H9A 108.8 . . ?
N1A C9A C10A 110.5(2) . . ?
C8A C9A H9A 108.8 . . ?
C8A C9A C10A 109.4(2) . . ?
C10A C9A H9A 108.8 . . ?
C9A C10A H10A 108.7 . . ?
C9A C10A H10B 108.7 . . ?
H10A C10A H10B 107.6 . . ?
C11A C10A C9A 114.0(3) . . ?
C11A C10A H10A 108.7 . . ?
C11A C10A H10B 108.7 . . ?
C10A C11A H11A 108.8 . . ?
C12A C11A C10A 110.9(3) . . ?
C12A C11A H11A 108.8 . . ?
C12A C11A C13A 109.7(3) . . ?
C13A C11A C10A 109.9(3) . . ?
C13A C11A H11A 108.8 . . ?
C11A C12A H12A 109.5 . . ?
C11A C12A H12B 109.5 . . ?
C11A C12A H12C 109.5 . . ?
H12A C12A H12B 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C11A C13A H13A 109.5 . . ?
C11A C13A H13B 109.5 . . ?
C11A C13A H13C 109.5 . . ?
H13A C13A H13B 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C5A C14A H14A 109.5 . . ?
C5A C14A H14B 109.5 . . ?
C5A C14A H14C 109.5 . . ?
H14A C14A H14B 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C8B O2B H2B 112(3) . . ?
C1B N1B H1B 122(3) . . ?
C1B N1B C9B 119.7(2) . . ?
C9B N1B H1B 117(3) . . ?
O1B C1B N1B 120.3(3) . . ?
O1B C1B C2B 120.9(3) . . ?
N1B C1B C2B 118.9(2) . . ?
C3B C2B C1B 118.0(3) . . ?
C3B C2B C7B 118.4(3) . . ?
C7B C2B C1B 123.6(3) . . ?
C2B C3B H3B 119.4 . . ?
C4B C3B C2B 121.2(3) . . ?
C4B C3B H3B 119.4 . . ?
C3B C4B H4B 120.5 . . ?
C3B C4B C5B 119.0(3) . . ?
C5B C4B H4B 120.5 . . ?
C4B C5B Cl1B 119.5(2) . . ?
C6B C5B Cl1B 119.7(3) . . ?
C6B C5B C4B 120.9(3) . . ?
C5B C6B H6B 120.1 . . ?
C5B C6B C7B 119.8(3) . . ?
C7B C6B H6B 120.1 . . ?
C2B C7B H7B 119.6 . . ?
C6B C7B C2B 120.8(3) . . ?
C6B C7B H7B 119.6 . . ?
O2B C8B C9B 112.8(2) . . ?
O3B C8B O2B 124.3(3) . . ?
O3B C8B C9B 122.8(3) . . ?
N1B C9B C8B 110.3(2) . . ?
N1B C9B H9B 108.6 . . ?
N1B C9B C10B 111.0(2) . . ?
C8B C9B H9B 108.6 . . ?
C8B C9B C10B 109.6(2) . . ?
C10B C9B H9B 108.6 . . ?
C9B C10B H10C 108.9 . . ?
C9B C10B H10D 108.9 . . ?
H10C C10B H10D 107.7 . . ?
C11B C10B C9B 113.5(3) . . ?
C11B C10B H10C 108.9 . . ?
C11B C10B H10D 108.9 . . ?
C10B C11B H11B 108.9 . . ?
C12B C11B C10B 110.5(3) . . ?
C12B C11B H11B 108.9 . . ?
C12B C11B C13B 109.6(3) . . ?
C13B C11B C10B 110.0(3) . . ?
C13B C11B H11B 108.9 . . ?
C11B C12B H12D 109.5 . . ?
C11B C12B H12E 109.5 . . ?
C11B C12B H12F 109.5 . . ?
H12D C12B H12E 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
C11B C13B H13D 109.5 . . ?
C11B C13B H13E 109.5 . . ?
C11B C13B H13F 109.5 . . ?
H13D C13B H13E 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?

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
O2A H2A O3B 0.85(3) 1.80(3) 2.631(3) 166(4) . yes
N1A H1A O1B 0.82(2) 2.17(3) 2.957(3) 162(4) 2_655 yes
O2B H2B O3A 0.84(3) 1.81(3) 2.629(3) 165(4) . yes
N1B H1B O1A 0.82(2) 2.12(2) 2.931(3) 172(4) 2_646 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
O1A C1A C2A C3A -7.0(4) . . . . ?
O1A C1A C2A C7A 173.4(3) . . . . ?
O2A C8A C9A N1A -160.5(3) . . . . ?
O2A C8A C9A C10A 77.7(3) . . . . ?
O3A C8A C9A N1A 21.9(4) . . . . ?
O3A C8A C9A C10A -99.9(3) . . . . ?
N1A C1A C2A C3A 172.6(3) . . . . ?
N1A C1A C2A C7A -7.1(4) . . . . ?
N1A C9A C10A C11A 75.4(3) . . . . ?
C1A N1A C9A C8A 68.6(3) . . . . ?
C1A N1A C9A C10A -170.3(3) . . . . ?
C1A C2A C3A C4A -178.0(3) . . . . ?
C1A C2A C7A C6A 178.4(3) . . . . ?
C2A C3A C4A C5A -0.1(5) . . . . ?
C3A C2A C7A C6A -1.2(5) . . . . ?
C3A C4A C5A C6A -1.9(5) . . . . ?
C3A C4A C5A C14A 179.5(3) . . . . ?
C4A C5A C6A C7A 2.3(5) . . . . ?
C5A C6A C7A C2A -0.8(5) . . . . ?
C7A C2A C3A C4A 1.7(5) . . . . ?
C8A C9A C10A C11A -162.8(3) . . . . ?
C9A N1A C1A O1A 7.7(4) . . . . ?
C9A N1A C1A C2A -171.8(2) . . . . ?
C9A C10A C11A C12A 75.1(4) . . . . ?
C9A C10A C11A C13A -163.4(3) . . . . ?
C14A C5A C6A C7A -179.0(3) . . . . ?
Cl1B C5B C6B C7B 178.3(3) . . . . ?
O1B C1B C2B C3B 8.6(4) . . . . ?
O1B C1B C2B C7B -171.3(3) . . . . ?
O2B C8B C9B N1B 160.9(3) . . . . ?
O2B C8B C9B C10B -76.5(3) . . . . ?
O3B C8B C9B N1B -21.6(4) . . . . ?
O3B C8B C9B C10B 100.9(3) . . . . ?
N1B C1B C2B C3B -171.6(3) . . . . ?
N1B C1B C2B C7B 8.5(4) . . . . ?
N1B C9B C10B C11B -73.5(3) . . . . ?
C1B N1B C9B C8B -69.5(3) . . . . ?
C1B N1B C9B C10B 168.8(3) . . . . ?
C1B C2B C3B C4B 178.6(3) . . . . ?
C1B C2B C7B C6B -179.0(3) . . . . ?
C2B C3B C4B C5B 0.3(5) . . . . ?
C3B C2B C7B C6B 1.0(5) . . . . ?
C3B C4B C5B Cl1B -178.8(3) . . . . ?
C3B C4B C5B C6B 1.5(5) . . . . ?
C4B C5B C6B C7B -1.9(5) . . . . ?
C5B C6B C7B C2B 0.7(5) . . . . ?
C7B C2B C3B C4B -1.4(5) . . . . ?
C8B C9B C10B C11B 164.4(3) . . . . ?
C9B N1B C1B O1B -6.9(4) . . . . ?
C9B N1B C1B C2B 173.3(2) . . . . ?
C9B C10B C11B C12B -75.3(3) . . . . ?
C9B C10B C11B C13B 163.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
####################################################################### 
# 
# 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_21kaw43_a
_database_code_depnum_ccdc_archive 'CCDC 2312807'
loop_
_audit_author_name
_audit_author_address
'Kraig Wheeler'
;Whitworth University
United States of America
;
_audit_update_record             
;
2023-12-18 deposited with the CCDC.	2024-02-12 downloaded from the CCDC.
;
_audit_creation_date             2023-12-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 Cl N O3, C14 H19 N O3'
_chemical_formula_sum            'C30 H33 Cl N2 O6'
_chemical_formula_weight         553.03
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.7599(5)
_cell_length_b                   9.7943(5)
_cell_length_c                   14.5273(6)
_cell_angle_alpha                90
_cell_angle_beta                 111.649(3)
_cell_angle_gamma                90
_cell_volume                     1422.98(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9763
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.07
_cell_measurement_theta_min      3.27
_shelx_estimated_absorpt_T_max   0.932
_shelx_estimated_absorpt_T_min   0.827
_exptl_absorpt_coefficient_mu    1.564
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6341
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.126
_exptl_crystal_size_mid          0.116
_exptl_crystal_size_min          0.046
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0739
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            47892
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.240
_diffrn_reflns_theta_min         3.273
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'κ-geometry four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'focusing mirror'
_diffrn_radiation_detector       'Bruker PHOTON II'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.817
_reflns_Friedel_fraction_full    0.941
_reflns_Friedel_fraction_max     0.922
_reflns_number_gt                4855
_reflns_number_total             5386
_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       'SAINT+ V8.40B (Bruker AXS Inc., 2020)'
_computing_data_collection       'APEX5 Ver.2022.08-RC130 (Bruker-AXS, 2023)'
_computing_data_reduction        'SAINT+ Ve8.40B (Bruker-AXS, 2020)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2019/1)'
_computing_structure_solution    'XT (Sheldrick, 2018/2)'
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 1910 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.056(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         5386
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0380
_refine_ls_restrained_S_all      1.050
_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)+(0.0269P)²+0.6982P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0798
_refine_ls_wR_factor_ref         0.0835
_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron density map and refined using anisotropic displacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv of the connected C atoms (1.5xUeqiv for methyl groups). Those H atoms
 attached to nitrogen and oxygen were located in Fourier diff maps  and assigned Uiso = 1.2xUeqiv.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9A(H9A), C9B(H9B), C11B(H11B)
2.b Secondary CH2 refined with riding coordinates:
 C10A(H10C,H10D), C10B(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C4A(H4A), C6A(H6A), C7A(H7A), C12A(H12D), C13A(H13D), C14A(H14D),
 C15A(H15A), C16A(H16A), C3B(H3B), C4B(H4B), C6B(H6B), C7B(H7B)
2.d Idealised Me refined as rotating group:
 C12B(H12A,H12B,H12C), C13B(H13A,H13B,H13C), C14B(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
Cl1A Cl 0.86878(8) 1.07174(9) 0.68191(6) 0.0312(2) Uani 1 1 d . . . . .
O1A O 0.5171(2) 0.7618(2) 0.92068(14) 0.0219(5) Uani 1 1 d . . . . .
O2A O 0.3498(2) 0.4332(3) 0.93772(16) 0.0253(5) Uani 1 1 d . . . . .
H2A H 0.397(4) 0.376(5) 0.984(3) 0.038 Uiso 1 1 d . U . . .
O3A O 0.5318(2) 0.4418(2) 0.89708(14) 0.0211(5) Uani 1 1 d . . . . .
N1A N 0.4251(3) 0.6599(3) 0.77215(18) 0.0174(5) Uani 1 1 d . . . . .
H1A H 0.437(3) 0.635(4) 0.719(3) 0.021 Uiso 1 1 d . U . . .
C1A C 0.5119(3) 0.7477(3) 0.8344(2) 0.0178(6) Uani 1 1 d . . . . .
C2A C 0.6000(3) 0.8252(3) 0.7938(2) 0.0178(6) Uani 1 1 d . . . . .
C3A C 0.7228(3) 0.8733(3) 0.8596(2) 0.0213(7) Uani 1 1 d . . . . .
H3A H 0.749085 0.854774 0.928331 0.026 Uiso 1 1 calc R U . . .
C4A C 0.8067(3) 0.9476(4) 0.8257(2) 0.0240(7) Uani 1 1 d . . . . .
H4A H 0.890215 0.980116 0.870675 0.029 Uiso 1 1 calc R U . . .
C5A C 0.7670(3) 0.9739(3) 0.7249(2) 0.0233(7) Uani 1 1 d . . . . .
C6A C 0.6468(3) 0.9258(3) 0.6580(2) 0.0216(7) Uani 1 1 d . . . . .
H6A H 0.621872 0.943249 0.589191 0.026 Uiso 1 1 calc R U . . .
C7A C 0.5626(3) 0.8512(3) 0.6927(2) 0.0200(7) Uani 1 1 d . . . . .
H7A H 0.479543 0.818137 0.647395 0.024 Uiso 1 1 calc R U . . .
C8A C 0.4184(3) 0.4774(3) 0.8846(2) 0.0186(6) Uani 1 1 d . . . . .
C9A C 0.3371(3) 0.5781(3) 0.80448(19) 0.0175(6) Uani 1 1 d . . . . .
H9A H 0.286987 0.640101 0.833264 0.021 Uiso 1 1 calc R U . . .
C10A C 0.2353(3) 0.5032(3) 0.7146(2) 0.0203(7) Uani 1 1 d . . . . .
H10C H 0.283871 0.452490 0.679283 0.024 Uiso 1 1 calc R U . . .
H10D H 0.184796 0.436178 0.738139 0.024 Uiso 1 1 calc R U . . .
C11A C 0.1386(3) 0.6023(3) 0.6438(2) 0.0201(6) Uani 1 1 d . . . . .
C12A C 0.1659(3) 0.6659(3) 0.5674(2) 0.0244(7) Uani 1 1 d . . . . .
H12D H 0.245251 0.643597 0.556447 0.029 Uiso 1 1 calc R U . . .
C13A C 0.0775(3) 0.7619(4) 0.5071(2) 0.0294(8) Uani 1 1 d . . . . .
H13D H 0.097496 0.805380 0.455809 0.035 Uiso 1 1 calc R U . . .
C14A C -0.0390(3) 0.7942(3) 0.5214(2) 0.0291(8) Uani 1 1 d . . . . .
H14D H -0.098426 0.860378 0.480317 0.035 Uiso 1 1 calc R U . . .
C15A C -0.0692(3) 0.7300(4) 0.5958(3) 0.0303(7) Uani 1 1 d . . . . .
H15A H -0.149880 0.750736 0.605325 0.036 Uiso 1 1 calc R U . . .
C16A C 0.0195(3) 0.6353(3) 0.6559(2) 0.0255(7) Uani 1 1 d . . . . .
H16A H -0.001376 0.591623 0.706827 0.031 Uiso 1 1 calc R U . . .
O1B O 0.4895(2) 0.2209(2) 0.58335(15) 0.0235(5) Uani 1 1 d . . . . .
O2B O 0.6361(2) 0.5341(3) 0.54114(16) 0.0259(5) Uani 1 1 d . . . . .
H2B H 0.591(4) 0.592(5) 0.501(3) 0.039 Uiso 1 1 d . U . . .
O3B O 0.4700(2) 0.5476(2) 0.59880(14) 0.0222(5) Uani 1 1 d . . . . .
N1B N 0.5859(3) 0.3316(3) 0.72761(19) 0.0195(6) Uani 1 1 d . . . . .
H1B H 0.580(4) 0.353(4) 0.781(3) 0.023 Uiso 1 1 d . U . . .
C1B C 0.4998(3) 0.2386(3) 0.6711(2) 0.0202(7) Uani 1 1 d . . . . .
C2B C 0.4202(3) 0.1599(3) 0.7181(2) 0.0193(6) Uani 1 1 d . . . . .
C3B C 0.3002(3) 0.0986(4) 0.6588(2) 0.0238(7) Uani 1 1 d . . . . .
H3B H 0.270085 0.107065 0.588818 0.029 Uiso 1 1 calc R U . . .
C4B C 0.2247(3) 0.0256(4) 0.7012(2) 0.0254(7) Uani 1 1 d . . . . .
H4B H 0.143340 -0.015714 0.659931 0.030 Uiso 1 1 calc R U . . .
C5B C 0.2665(3) 0.0120(3) 0.8035(2) 0.0232(7) Uani 1 1 d . . . . .
C6B C 0.3864(3) 0.0741(3) 0.8625(2) 0.0226(6) Uani 1 1 d . . . . .
H6B H 0.415538 0.067117 0.932480 0.027 Uiso 1 1 calc R U . . .
C7B C 0.4632(3) 0.1452(3) 0.8209(2) 0.0215(7) Uani 1 1 d . . . . .
H7B H 0.545723 0.184433 0.862273 0.026 Uiso 1 1 calc R U . . .
C8B C 0.5779(3) 0.5038(3) 0.6042(2) 0.0190(6) Uani 1 1 d . . . . .
C9B C 0.6667(3) 0.4142(3) 0.6879(2) 0.0197(6) Uani 1 1 d . . . . .
H9B H 0.719961 0.352476 0.661678 0.024 Uiso 1 1 calc R U . . .
C10B C 0.7633(3) 0.5062(3) 0.7690(2) 0.0211(7) Uani 1 1 d . . . . .
H10A H 0.784745 0.586881 0.736572 0.025 Uiso 1 1 calc R U . . .
H10B H 0.715785 0.539591 0.811460 0.025 Uiso 1 1 calc R U . . .
C11B C 0.8948(3) 0.4410(4) 0.8358(2) 0.0259(7) Uani 1 1 d . . . . .
H11B H 0.942597 0.406893 0.793010 0.031 Uiso 1 1 calc R U . . .
C12B C 0.8747(4) 0.3211(4) 0.8959(3) 0.0350(8) Uani 1 1 d . . . . .
H12A H 0.961946 0.287639 0.940551 0.053 Uiso 1 1 calc R U . . .
H12B H 0.827116 0.247630 0.850868 0.053 Uiso 1 1 calc R U . . .
H12C H 0.822157 0.350981 0.934768 0.053 Uiso 1 1 calc R U . . .
C13B C 0.9817(3) 0.5503(4) 0.9051(2) 0.0321(8) Uani 1 1 d . . . . .
H13A H 0.941630 0.577331 0.952944 0.048 Uiso 1 1 calc R U . . .
H13B H 0.987625 0.630099 0.866179 0.048 Uiso 1 1 calc R U . . .
H13C H 1.071462 0.513622 0.940444 0.048 Uiso 1 1 calc R U . . .
C14B C 0.1853(4) -0.0685(4) 0.8514(2) 0.0309(8) Uani 1 1 d . . . . .
H14A H 0.139047 -0.004994 0.880086 0.046 Uiso 1 1 calc R U . . .
H14B H 0.245256 -0.126952 0.903773 0.046 Uiso 1 1 calc R U . . .
H14C H 0.119436 -0.125193 0.801339 0.046 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
Cl1A C5A 1.736(3) . ?
O1A C1A 1.242(3) . ?
O2A H2A 0.88(4) . ?
O2A C8A 1.322(4) . ?
O3A C8A 1.217(4) . ?
N1A H1A 0.86(3) . ?
N1A C1A 1.344(4) . ?
N1A C9A 1.444(4) . ?
C1A C2A 1.495(4) . ?
C2A C3A 1.396(4) . ?
C2A C7A 1.396(4) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.383(4) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.389(4) . ?
C5A C6A 1.383(5) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.394(4) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.530(4) . ?
C9A H9A 1.0000 . ?
C9A C10A 1.545(4) . ?
C10A H10C 0.9900 . ?
C10A H10D 0.9900 . ?
C10A C11A 1.515(4) . ?
C11A C12A 1.396(4) . ?
C11A C16A 1.394(4) . ?
C12A H12D 0.9500 . ?
C12A C13A 1.393(5) . ?
C13A H13D 0.9500 . ?
C13A C14A 1.380(5) . ?
C14A H14D 0.9500 . ?
C14A C15A 1.389(5) . ?
C15A H15A 0.9500 . ?
C15A C16A 1.386(5) . ?
C16A H16A 0.9500 . ?
O1B C1B 1.251(3) . ?
O2B H2B 0.83(5) . ?
O2B C8B 1.320(4) . ?
O3B C8B 1.213(4) . ?
N1B H1B 0.83(4) . ?
N1B C1B 1.342(4) . ?
N1B C9B 1.454(4) . ?
C1B C2B 1.492(4) . ?
C2B C3B 1.395(4) . ?
C2B C7B 1.398(4) . ?
C3B H3B 0.9500 . ?
C3B C4B 1.386(4) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.390(4) . ?
C5B C6B 1.398(4) . ?
C5B C14B 1.522(4) . ?
C6B H6B 0.9500 . ?
C6B C7B 1.379(4) . ?
C7B H7B 0.9500 . ?
C8B C9B 1.518(4) . ?
C9B H9B 1.0000 . ?
C9B C10B 1.542(4) . ?
C10B H10A 0.9900 . ?
C10B H10B 0.9900 . ?
C10B C11B 1.529(4) . ?
C11B H11B 1.0000 . ?
C11B C12B 1.525(5) . ?
C11B C13B 1.529(5) . ?
C12B H12A 0.9800 . ?
C12B H12B 0.9800 . ?
C12B H12C 0.9800 . ?
C13B H13A 0.9800 . ?
C13B H13B 0.9800 . ?
C13B H13C 0.9800 . ?
C14B H14A 0.9800 . ?
C14B H14B 0.9800 . ?
C14B H14C 0.9800 . ?

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
C8A O2A H2A 112(3) . . ?
C1A N1A H1A 119(2) . . ?
C1A N1A C9A 120.8(2) . . ?
C9A N1A H1A 118(2) . . ?
O1A C1A N1A 120.7(3) . . ?
O1A C1A C2A 122.9(3) . . ?
N1A C1A C2A 116.4(2) . . ?
C3A C2A C1A 118.7(3) . . ?
C3A C2A C7A 119.4(3) . . ?
C7A C2A C1A 121.9(3) . . ?
C2A C3A H3A 119.6 . . ?
C4A C3A C2A 120.7(3) . . ?
C4A C3A H3A 119.6 . . ?
C3A C4A H4A 120.5 . . ?
C3A C4A C5A 119.0(3) . . ?
C5A C4A H4A 120.5 . . ?
C4A C5A Cl1A 119.5(3) . . ?
C6A C5A Cl1A 119.1(2) . . ?
C6A C5A C4A 121.4(3) . . ?
C5A C6A H6A 120.4 . . ?
C5A C6A C7A 119.2(3) . . ?
C7A C6A H6A 120.4 . . ?
C2A C7A H7A 119.9 . . ?
C6A C7A C2A 120.1(3) . . ?
C6A C7A H7A 119.9 . . ?
O2A C8A C9A 111.7(3) . . ?
O3A C8A O2A 124.4(3) . . ?
O3A C8A C9A 124.0(3) . . ?
N1A C9A C8A 110.2(2) . . ?
N1A C9A H9A 108.6 . . ?
N1A C9A C10A 109.5(2) . . ?
C8A C9A H9A 108.6 . . ?
C8A C9A C10A 111.4(3) . . ?
C10A C9A H9A 108.6 . . ?
C9A C10A H10C 109.4 . . ?
C9A C10A H10D 109.4 . . ?
H10C C10A H10D 108.0 . . ?
C11A C10A C9A 111.4(3) . . ?
C11A C10A H10C 109.4 . . ?
C11A C10A H10D 109.4 . . ?
C12A C11A C10A 122.1(3) . . ?
C16A C11A C10A 119.8(3) . . ?
C16A C11A C12A 118.1(3) . . ?
C11A C12A H12D 119.8 . . ?
C13A C12A C11A 120.4(3) . . ?
C13A C12A H12D 119.8 . . ?
C12A C13A H13D 119.7 . . ?
C14A C13A C12A 120.5(3) . . ?
C14A C13A H13D 119.7 . . ?
C13A C14A H14D 120.0 . . ?
C13A C14A C15A 119.9(3) . . ?
C15A C14A H14D 120.0 . . ?
C14A C15A H15A 120.3 . . ?
C16A C15A C14A 119.3(3) . . ?
C16A C15A H15A 120.3 . . ?
C11A C16A H16A 119.1 . . ?
C15A C16A C11A 121.8(3) . . ?
C15A C16A H16A 119.1 . . ?
C8B O2B H2B 110(3) . . ?
C1B N1B H1B 118(3) . . ?
C1B N1B C9B 120.9(3) . . ?
C9B N1B H1B 120(3) . . ?
O1B C1B N1B 119.9(3) . . ?
O1B C1B C2B 123.0(3) . . ?
N1B C1B C2B 117.0(3) . . ?
C3B C2B C1B 119.8(3) . . ?
C3B C2B C7B 118.8(3) . . ?
C7B C2B C1B 121.4(3) . . ?
C2B C3B H3B 119.7 . . ?
C4B C3B C2B 120.5(3) . . ?
C4B C3B H3B 119.7 . . ?
C3B C4B H4B 119.6 . . ?
C3B C4B C5B 120.9(3) . . ?
C5B C4B H4B 119.6 . . ?
C4B C5B C6B 118.3(3) . . ?
C4B C5B C14B 121.6(3) . . ?
C6B C5B C14B 120.0(3) . . ?
C5B C6B H6B 119.4 . . ?
C7B C6B C5B 121.2(3) . . ?
C7B C6B H6B 119.4 . . ?
C2B C7B H7B 119.9 . . ?
C6B C7B C2B 120.2(3) . . ?
C6B C7B H7B 119.9 . . ?
O2B C8B C9B 111.5(3) . . ?
O3B C8B O2B 124.3(3) . . ?
O3B C8B C9B 124.1(3) . . ?
N1B C9B C8B 110.4(3) . . ?
N1B C9B H9B 109.0 . . ?
N1B C9B C10B 110.8(2) . . ?
C8B C9B H9B 109.0 . . ?
C8B C9B C10B 108.8(3) . . ?
C10B C9B H9B 109.0 . . ?
C9B C10B H10A 108.2 . . ?
C9B C10B H10B 108.2 . . ?
H10A C10B H10B 107.3 . . ?
C11B C10B C9B 116.5(3) . . ?
C11B C10B H10A 108.2 . . ?
C11B C10B H10B 108.2 . . ?
C10B C11B H11B 108.2 . . ?
C10B C11B C13B 108.8(3) . . ?
C12B C11B C10B 113.1(3) . . ?
C12B C11B H11B 108.2 . . ?
C12B C11B C13B 110.1(3) . . ?
C13B C11B H11B 108.2 . . ?
C11B C12B H12A 109.5 . . ?
C11B C12B H12B 109.5 . . ?
C11B C12B H12C 109.5 . . ?
H12A C12B H12B 109.5 . . ?
H12A C12B H12C 109.5 . . ?
H12B C12B H12C 109.5 . . ?
C11B C13B H13A 109.5 . . ?
C11B C13B H13B 109.5 . . ?
C11B C13B H13C 109.5 . . ?
H13A C13B H13B 109.5 . . ?
H13A C13B H13C 109.5 . . ?
H13B C13B H13C 109.5 . . ?
C5B C14B H14A 109.5 . . ?
C5B C14B H14B 109.5 . . ?
C5B C14B H14C 109.5 . . ?
H14A C14B H14B 109.5 . . ?
H14A C14B H14C 109.5 . . ?
H14B C14B H14C 109.5 . . ?

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
O2A H2A O1A 0.88(4) 1.75(4) 2.632(3) 177(4) 2_647 yes
N1A H1A O3B 0.86(3) 2.09(4) 2.947(3) 172(3) . yes
O2B H2B O1B 0.83(5) 1.75(5) 2.577(3) 175(4) 2_656 yes
N1B H1B O3A 0.83(4) 2.12(4) 2.936(3) 166(4) . 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
Cl1A C5A C6A C7A -177.7(2) . . . . ?
O1A C1A C2A C3A 25.2(5) . . . . ?
O1A C1A C2A C7A -154.4(3) . . . . ?
O2A C8A C9A N1A 159.7(2) . . . . ?
O2A C8A C9A C10A -78.6(3) . . . . ?
O3A C8A C9A N1A -20.9(4) . . . . ?
O3A C8A C9A C10A 100.8(3) . . . . ?
N1A C1A C2A C3A -154.7(3) . . . . ?
N1A C1A C2A C7A 25.7(4) . . . . ?
N1A C9A C10A C11A -68.0(3) . . . . ?
C1A N1A C9A C8A -65.3(4) . . . . ?
C1A N1A C9A C10A 171.9(3) . . . . ?
C1A C2A C3A C4A -178.9(3) . . . . ?
C1A C2A C7A C6A 179.0(3) . . . . ?
C2A C3A C4A C5A 0.0(5) . . . . ?
C3A C2A C7A C6A -0.6(5) . . . . ?
C3A C4A C5A Cl1A 177.9(3) . . . . ?
C3A C4A C5A C6A -1.0(5) . . . . ?
C4A C5A C6A C7A 1.2(5) . . . . ?
C5A C6A C7A C2A -0.4(5) . . . . ?
C7A C2A C3A C4A 0.8(5) . . . . ?
C8A C9A C10A C11A 169.9(2) . . . . ?
C9A N1A C1A O1A -1.1(4) . . . . ?
C9A N1A C1A C2A 178.9(3) . . . . ?
C9A C10A C11A C12A 88.2(3) . . . . ?
C9A C10A C11A C16A -90.0(3) . . . . ?
C10A C11A C12A C13A -176.6(3) . . . . ?
C10A C11A C16A C15A 177.1(3) . . . . ?
C11A C12A C13A C14A -0.7(5) . . . . ?
C12A C11A C16A C15A -1.2(5) . . . . ?
C12A C13A C14A C15A -0.6(5) . . . . ?
C13A C14A C15A C16A 1.0(5) . . . . ?
C14A C15A C16A C11A -0.1(5) . . . . ?
C16A C11A C12A C13A 1.6(5) . . . . ?
O1B C1B C2B C3B -22.4(5) . . . . ?
O1B C1B C2B C7B 157.3(3) . . . . ?
O2B C8B C9B N1B -153.3(3) . . . . ?
O2B C8B C9B C10B 85.0(3) . . . . ?
O3B C8B C9B N1B 30.2(4) . . . . ?
O3B C8B C9B C10B -91.6(4) . . . . ?
N1B C1B C2B C3B 157.9(3) . . . . ?
N1B C1B C2B C7B -22.4(4) . . . . ?
N1B C9B C10B C11B 83.5(3) . . . . ?
C1B N1B C9B C8B 63.0(4) . . . . ?
C1B N1B C9B C10B -176.5(3) . . . . ?
C1B C2B C3B C4B -179.7(3) . . . . ?
C1B C2B C7B C6B 178.8(3) . . . . ?
C2B C3B C4B C5B 0.1(5) . . . . ?
C3B C2B C7B C6B -1.5(5) . . . . ?
C3B C4B C5B C6B 0.1(5) . . . . ?
C3B C4B C5B C14B -179.7(3) . . . . ?
C4B C5B C6B C7B -1.1(5) . . . . ?
C5B C6B C7B C2B 1.8(5) . . . . ?
C7B C2B C3B C4B 0.5(5) . . . . ?
C8B C9B C10B C11B -155.0(3) . . . . ?
C9B N1B C1B O1B 1.0(4) . . . . ?
C9B N1B C1B C2B -179.3(3) . . . . ?
C9B C10B C11B C12B -62.1(4) . . . . ?
C9B C10B C11B C13B 175.1(3) . . . . ?
C14B C5B C6B C7B 178.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
####################################################################### 
# 
# 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_21kaw46_a
_database_code_depnum_ccdc_archive 'CCDC 2312806'
loop_
_audit_author_name
_audit_author_address
'Kraig Wheeler'
;Whitworth University
United States of America
;
_audit_update_record             
;
2023-12-08 deposited with the CCDC.	2024-02-12 downloaded from the CCDC.
;
_audit_creation_date             2023-10-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 Cl N O3, C13 H16 Cl N O3'
_chemical_formula_sum            'C29 H30 Cl2 N2 O6'
_chemical_formula_weight         573.45
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.7438(4)
_cell_length_b                   9.7103(3)
_cell_length_c                   14.4644(5)
_cell_angle_alpha                90
_cell_angle_beta                 110.923(2)
_cell_angle_gamma                90
_cell_volume                     1409.50(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9919
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.03
_cell_measurement_theta_min      3.27
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.451
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6335
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             600
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 1.00 0.00 0.2450
0.00 -1.00 0.00 0.2070
-1.00 0.00 -1.00 0.0260
1.00 0.00 1.00 0.0260
-1.00 0.00 0.00 0.0320
1.00 0.00 -1.00 0.0230
-1.00 0.00 1.00 0.0360
-1.00 -1.00 0.00 0.1300
0.00 0.00 1.00 0.0310

_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.052
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            28644
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.073
_diffrn_reflns_theta_min         3.271
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'κ-geometry four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'focusing mirror'
_diffrn_radiation_detector       'Bruker PHOTON II'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.848
_reflns_Friedel_fraction_full    0.971
_reflns_Friedel_fraction_max     0.962
_reflns_number_gt                4917
_reflns_number_total             5253
_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       'SAINT+ V8.40B (Bruker AXS Inc., 2020)'
_computing_data_collection       'APEX4 Ver. 8.38A (Bruker-AXS, 2022)'
_computing_data_reduction        'SAINT+ Ve8.40B (Bruker-AXS, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2018/2)'
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 2120 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.050(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         5253
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0278
_refine_ls_restrained_S_all      1.040
_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)+(0.0279P)²+0.3170P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0638
_refine_ls_wR_factor_ref         0.0658
_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron density map and refined using anisotropic displacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv of the connected C atoms (1.5xUeqiv for methyl groups). Those H atoms
 attached to nitrogen and oxygen were located in Fourier diff maps and assigned Uiso = 1.2xUeqiv for nitrogen (1.5xUeqiv for oxygen).
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9A(H9A), C9B(H9B), C11B(H11B)
2.b Secondary CH2 refined with riding coordinates:
 C10A(H10A,H10B), C10B(H10C,H10D)
2.c Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C4A(H4A), C6A(H6A), C7A(H7A), C12A(H12A), C13A(H13A), C14A(H14A),
 C15A(H15A), C16A(H16A), C3B(H3B), C4B(H4B), C6B(H6B), C7B(H7B)
2.d Idealised Me refined as rotating group:
 C12B(H12B,H12C,H12D), C13B(H13B,H13C,H13D)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
Cl1A Cl 0.87027(6) 1.08196(7) 0.67830(5) 0.02469(15) Uani 1 1 d . . . . .
O1A O 0.52123(17) 0.7704(2) 0.92218(12) 0.0176(4) Uani 1 1 d . . . . .
O2A O 0.34638(18) 0.4480(2) 0.94140(13) 0.0227(4) Uani 1 1 d . . . . .
H2A H 0.388(3) 0.384(4) 0.984(2) 0.027 Uiso 1 1 d . U . . .
O3A O 0.52514(17) 0.4496(2) 0.89621(12) 0.0175(4) Uani 1 1 d . . . . .
N1A N 0.4238(2) 0.6717(2) 0.77269(16) 0.0148(4) Uani 1 1 d . . . . .
H1A H 0.436(3) 0.647(3) 0.720(2) 0.018 Uiso 1 1 d . U . . .
C1A C 0.5140(2) 0.7567(3) 0.83494(18) 0.0150(5) Uani 1 1 d . . . . .
C2A C 0.6028(3) 0.8326(3) 0.79342(19) 0.0155(5) Uani 1 1 d . . . . .
C3A C 0.7257(3) 0.8786(3) 0.85781(18) 0.0170(5) Uani 1 1 d . . . . .
H3A H 0.752095 0.858732 0.926460 0.020 Uiso 1 1 calc R U . . .
C4A C 0.8103(3) 0.9533(3) 0.82321(18) 0.0194(6) Uani 1 1 d . . . . .
H4A H 0.894275 0.984554 0.867394 0.023 Uiso 1 1 calc R U . . .
C5A C 0.7694(3) 0.9815(3) 0.72233(19) 0.0189(6) Uani 1 1 d . . . . .
C6A C 0.6497(3) 0.9349(3) 0.65672(18) 0.0188(5) Uani 1 1 d . . . . .
H6A H 0.624728 0.953601 0.587998 0.023 Uiso 1 1 calc R U . . .
C7A C 0.5654(3) 0.8601(3) 0.69193(19) 0.0170(5) Uani 1 1 d . . . . .
H7A H 0.482328 0.827526 0.647143 0.020 Uiso 1 1 calc R U . . .
C8A C 0.4137(3) 0.4893(3) 0.88581(17) 0.0155(5) Uani 1 1 d . . . . .
C9A C 0.3345(2) 0.5911(3) 0.80658(16) 0.0149(5) Uani 1 1 d . . . . .
H9A H 0.285270 0.654824 0.835743 0.018 Uiso 1 1 calc R U . . .
C10A C 0.2326(3) 0.5156(3) 0.71735(18) 0.0169(5) Uani 1 1 d . . . . .
H10A H 0.281040 0.462937 0.682149 0.020 Uiso 1 1 calc R U . . .
H10B H 0.181498 0.449206 0.741732 0.020 Uiso 1 1 calc R U . . .
C11A C 0.1370(2) 0.6144(3) 0.64579(18) 0.0169(5) Uani 1 1 d . . . . .
C12A C 0.0159(3) 0.6463(3) 0.6564(2) 0.0219(6) Uani 1 1 d . . . . .
H12A H -0.006000 0.603550 0.707639 0.026 Uiso 1 1 calc R U . . .
C13A C -0.0729(3) 0.7388(3) 0.5938(2) 0.0253(6) Uani 1 1 d . . . . .
H13A H -0.154959 0.758304 0.602028 0.030 Uiso 1 1 calc R U . . .
C14A C -0.0416(3) 0.8030(3) 0.5190(2) 0.0250(6) Uani 1 1 d . . . . .
H14A H -0.101293 0.867872 0.476729 0.030 Uiso 1 1 calc R U . . .
C15A C 0.0773(3) 0.7715(3) 0.50672(19) 0.0245(6) Uani 1 1 d . . . . .
H15A H 0.098847 0.814819 0.455489 0.029 Uiso 1 1 calc R U . . .
C16A C 0.1651(3) 0.6772(3) 0.56860(19) 0.0205(6) Uani 1 1 d . . . . .
H16A H 0.245314 0.655144 0.558327 0.025 Uiso 1 1 calc R U . . .
Cl1B Cl 0.16445(6) -0.08223(7) 0.85702(5) 0.02548(16) Uani 1 1 d . . . . .
O1B O 0.48298(18) 0.2221(2) 0.58541(13) 0.0199(4) Uani 1 1 d . . . . .
O2B O 0.63547(19) 0.5321(2) 0.54080(13) 0.0214(4) Uani 1 1 d . . . . .
H2B H 0.595(3) 0.588(4) 0.501(2) 0.026 Uiso 1 1 d . U . . .
O3B O 0.46897(17) 0.5529(2) 0.59873(12) 0.0184(4) Uani 1 1 d . . . . .
N1B N 0.5783(2) 0.3345(2) 0.72886(16) 0.0162(5) Uani 1 1 d . . . . .
H1B H 0.573(3) 0.353(4) 0.781(2) 0.019 Uiso 1 1 d . U . . .
C1B C 0.4931(2) 0.2416(3) 0.67328(18) 0.0158(5) Uani 1 1 d . . . . .
C2B C 0.4115(3) 0.1621(3) 0.72041(19) 0.0159(5) Uani 1 1 d . . . . .
C3B C 0.2939(2) 0.0993(3) 0.66027(18) 0.0184(5) Uani 1 1 d . . . . .
H3B H 0.266163 0.108130 0.590397 0.022 Uiso 1 1 calc R U . . .
C4B C 0.2168(3) 0.0239(3) 0.70158(19) 0.0203(6) Uani 1 1 d . . . . .
H4B H 0.136972 -0.019605 0.660537 0.024 Uiso 1 1 calc R U . . .
C5B C 0.2583(3) 0.0134(3) 0.80333(19) 0.0185(5) Uani 1 1 d . . . . .
C6B C 0.3744(3) 0.0756(3) 0.86516(18) 0.0191(5) Uani 1 1 d . . . . .
H6B H 0.400639 0.067998 0.935019 0.023 Uiso 1 1 calc R U . . .
C7B C 0.4516(3) 0.1492(3) 0.82313(19) 0.0175(5) Uani 1 1 d . . . . .
H7B H 0.532211 0.191102 0.864484 0.021 Uiso 1 1 calc R U . . .
C8B C 0.5761(3) 0.5059(3) 0.60433(17) 0.0153(5) Uani 1 1 d . . . . .
C9B C 0.6616(2) 0.4150(3) 0.68897(17) 0.0152(5) Uani 1 1 d . . . . .
H9B H 0.715338 0.351144 0.663820 0.018 Uiso 1 1 calc R U . . .
C10B C 0.7565(2) 0.5087(3) 0.76925(18) 0.0168(5) Uani 1 1 d . . . . .
H10C H 0.778366 0.589765 0.736368 0.020 Uiso 1 1 calc R U . . .
H10D H 0.708551 0.542701 0.811803 0.020 Uiso 1 1 calc R U . . .
C11B C 0.8873(3) 0.4424(3) 0.83576(18) 0.0206(6) Uani 1 1 d . . . . .
H11B H 0.936145 0.409348 0.792686 0.025 Uiso 1 1 calc R U . . .
C12B C 0.8660(3) 0.3199(3) 0.8942(2) 0.0298(7) Uani 1 1 d . . . . .
H12B H 0.816316 0.349746 0.935846 0.045 Uiso 1 1 calc R U . . .
H12C H 0.952553 0.282763 0.936140 0.045 Uiso 1 1 calc R U . . .
H12D H 0.815331 0.248524 0.848274 0.045 Uiso 1 1 calc R U . . .
C13B C 0.9735(3) 0.5517(3) 0.9064(2) 0.0286(7) Uani 1 1 d . . . . .
H13B H 0.932136 0.578136 0.954165 0.043 Uiso 1 1 calc R U . . .
H13C H 0.980888 0.632836 0.868362 0.043 Uiso 1 1 calc R U . . .
H13D H 1.062458 0.513997 0.941705 0.043 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
Cl1A C5A 1.739(3) . ?
O1A C1A 1.243(3) . ?
O2A H2A 0.88(4) . ?
O2A C8A 1.322(3) . ?
O3A C8A 1.214(3) . ?
N1A H1A 0.86(3) . ?
N1A C1A 1.345(3) . ?
N1A C9A 1.452(3) . ?
C1A C2A 1.492(4) . ?
C2A C3A 1.389(4) . ?
C2A C7A 1.402(4) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.389(4) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.393(4) . ?
C5A C6A 1.374(4) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.392(4) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.523(3) . ?
C9A H9A 1.0000 . ?
C9A C10A 1.547(3) . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C10A C11A 1.512(3) . ?
C11A C12A 1.398(4) . ?
C11A C16A 1.397(4) . ?
C12A H12A 0.9500 . ?
C12A C13A 1.385(4) . ?
C13A H13A 0.9500 . ?
C13A C14A 1.389(4) . ?
C14A H14A 0.9500 . ?
C14A C15A 1.385(4) . ?
C15A H15A 0.9500 . ?
C15A C16A 1.388(4) . ?
C16A H16A 0.9500 . ?
Cl1B C5B 1.744(3) . ?
O1B C1B 1.251(3) . ?
O2B H2B 0.80(4) . ?
O2B C8B 1.317(3) . ?
O3B C8B 1.214(3) . ?
N1B H1B 0.80(3) . ?
N1B C1B 1.332(4) . ?
N1B C9B 1.454(3) . ?
C1B C2B 1.502(4) . ?
C2B C3B 1.392(4) . ?
C2B C7B 1.397(4) . ?
C3B H3B 0.9500 . ?
C3B C4B 1.391(4) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.381(4) . ?
C5B C6B 1.387(4) . ?
C6B H6B 0.9500 . ?
C6B C7B 1.389(4) . ?
C7B H7B 0.9500 . ?
C8B C9B 1.523(3) . ?
C9B H9B 1.0000 . ?
C9B C10B 1.540(4) . ?
C10B H10C 0.9900 . ?
C10B H10D 0.9900 . ?
C10B C11B 1.532(3) . ?
C11B H11B 1.0000 . ?
C11B C12B 1.524(4) . ?
C11B C13B 1.533(4) . ?
C12B H12B 0.9800 . ?
C12B H12C 0.9800 . ?
C12B H12D 0.9800 . ?
C13B H13B 0.9800 . ?
C13B H13C 0.9800 . ?
C13B H13D 0.9800 . ?

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
C8A O2A H2A 113(2) . . ?
C1A N1A H1A 118(2) . . ?
C1A N1A C9A 120.6(2) . . ?
C9A N1A H1A 119(2) . . ?
O1A C1A N1A 120.9(2) . . ?
O1A C1A C2A 122.6(2) . . ?
N1A C1A C2A 116.4(2) . . ?
C3A C2A C1A 118.7(2) . . ?
C3A C2A C7A 119.3(2) . . ?
C7A C2A C1A 122.0(2) . . ?
C2A C3A H3A 119.5 . . ?
C4A C3A C2A 120.9(2) . . ?
C4A C3A H3A 119.5 . . ?
C3A C4A H4A 120.7 . . ?
C3A C4A C5A 118.5(2) . . ?
C5A C4A H4A 120.7 . . ?
C4A C5A Cl1A 119.3(2) . . ?
C6A C5A Cl1A 118.9(2) . . ?
C6A C5A C4A 121.8(3) . . ?
C5A C6A H6A 120.3 . . ?
C5A C6A C7A 119.3(2) . . ?
C7A C6A H6A 120.3 . . ?
C2A C7A H7A 120.0 . . ?
C6A C7A C2A 120.1(2) . . ?
C6A C7A H7A 120.0 . . ?
O2A C8A C9A 112.0(2) . . ?
O3A C8A O2A 123.9(2) . . ?
O3A C8A C9A 124.1(2) . . ?
N1A C9A C8A 110.17(19) . . ?
N1A C9A H9A 108.8 . . ?
N1A C9A C10A 109.25(19) . . ?
C8A C9A H9A 108.8 . . ?
C8A C9A C10A 111.0(2) . . ?
C10A C9A H9A 108.8 . . ?
C9A C10A H10A 109.2 . . ?
C9A C10A H10B 109.2 . . ?
H10A C10A H10B 107.9 . . ?
C11A C10A C9A 112.1(2) . . ?
C11A C10A H10A 109.2 . . ?
C11A C10A H10B 109.2 . . ?
C12A C11A C10A 119.8(2) . . ?
C16A C11A C10A 122.4(2) . . ?
C16A C11A C12A 117.8(2) . . ?
C11A C12A H12A 119.2 . . ?
C13A C12A C11A 121.5(3) . . ?
C13A C12A H12A 119.2 . . ?
C12A C13A H13A 120.1 . . ?
C12A C13A C14A 119.9(3) . . ?
C14A C13A H13A 120.1 . . ?
C13A C14A H14A 120.3 . . ?
C15A C14A C13A 119.4(3) . . ?
C15A C14A H14A 120.3 . . ?
C14A C15A H15A 119.7 . . ?
C14A C15A C16A 120.5(3) . . ?
C16A C15A H15A 119.7 . . ?
C11A C16A H16A 119.6 . . ?
C15A C16A C11A 120.8(3) . . ?
C15A C16A H16A 119.6 . . ?
C8B O2B H2B 111(2) . . ?
C1B N1B H1B 117(2) . . ?
C1B N1B C9B 120.8(2) . . ?
C9B N1B H1B 121(2) . . ?
O1B C1B N1B 120.5(2) . . ?
O1B C1B C2B 122.1(2) . . ?
N1B C1B C2B 117.5(2) . . ?
C3B C2B C1B 119.2(2) . . ?
C3B C2B C7B 119.5(2) . . ?
C7B C2B C1B 121.4(2) . . ?
C2B C3B H3B 119.7 . . ?
C4B C3B C2B 120.6(2) . . ?
C4B C3B H3B 119.7 . . ?
C3B C4B H4B 120.6 . . ?
C5B C4B C3B 118.8(2) . . ?
C5B C4B H4B 120.6 . . ?
C4B C5B Cl1B 119.7(2) . . ?
C4B C5B C6B 121.9(3) . . ?
C6B C5B Cl1B 118.3(2) . . ?
C5B C6B H6B 120.6 . . ?
C5B C6B C7B 118.8(2) . . ?
C7B C6B H6B 120.6 . . ?
C2B C7B H7B 119.8 . . ?
C6B C7B C2B 120.4(2) . . ?
C6B C7B H7B 119.8 . . ?
O2B C8B C9B 111.7(2) . . ?
O3B C8B O2B 124.4(2) . . ?
O3B C8B C9B 123.9(2) . . ?
N1B C9B C8B 110.5(2) . . ?
N1B C9B H9B 109.1 . . ?
N1B C9B C10B 110.75(19) . . ?
C8B C9B H9B 109.1 . . ?
C8B C9B C10B 108.1(2) . . ?
C10B C9B H9B 109.1 . . ?
C9B C10B H10C 108.3 . . ?
C9B C10B H10D 108.3 . . ?
H10C C10B H10D 107.4 . . ?
C11B C10B C9B 115.9(2) . . ?
C11B C10B H10C 108.3 . . ?
C11B C10B H10D 108.3 . . ?
C10B C11B H11B 108.1 . . ?
C10B C11B C13B 109.1(2) . . ?
C12B C11B C10B 113.0(2) . . ?
C12B C11B H11B 108.1 . . ?
C12B C11B C13B 110.2(2) . . ?
C13B C11B H11B 108.1 . . ?
C11B C12B H12B 109.5 . . ?
C11B C12B H12C 109.5 . . ?
C11B C12B H12D 109.5 . . ?
H12B C12B H12C 109.5 . . ?
H12B C12B H12D 109.5 . . ?
H12C C12B H12D 109.5 . . ?
C11B C13B H13B 109.5 . . ?
C11B C13B H13C 109.5 . . ?
C11B C13B H13D 109.5 . . ?
H13B C13B H13C 109.5 . . ?
H13B C13B H13D 109.5 . . ?
H13C C13B H13D 109.5 . . ?

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
O2A H2A O1A 0.88(4) 1.74(4) 2.624(3) 174(3) 2_647 yes
N1A H1A O3B 0.86(3) 2.11(3) 2.961(3) 171(3) . yes
O2B H2B O1B 0.80(4) 1.79(4) 2.588(3) 175(4) 2_656 yes
N1B H1B O3A 0.80(3) 2.13(3) 2.902(3) 163(3) . 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
Cl1A C5A C6A C7A -176.9(2) . . . . ?
O1A C1A C2A C3A 24.2(4) . . . . ?
O1A C1A C2A C7A -155.0(2) . . . . ?
O2A C8A C9A N1A 158.7(2) . . . . ?
O2A C8A C9A C10A -80.1(3) . . . . ?
O3A C8A C9A N1A -21.9(3) . . . . ?
O3A C8A C9A C10A 99.3(3) . . . . ?
N1A C1A C2A C3A -155.9(2) . . . . ?
N1A C1A C2A C7A 24.9(4) . . . . ?
N1A C9A C10A C11A -68.0(3) . . . . ?
C1A N1A C9A C8A -63.8(3) . . . . ?
C1A N1A C9A C10A 173.9(2) . . . . ?
C1A C2A C3A C4A -178.0(2) . . . . ?
C1A C2A C7A C6A 178.0(2) . . . . ?
C2A C3A C4A C5A 0.1(4) . . . . ?
C3A C2A C7A C6A -1.2(4) . . . . ?
C3A C4A C5A Cl1A 176.9(2) . . . . ?
C3A C4A C5A C6A -1.4(4) . . . . ?
C4A C5A C6A C7A 1.4(4) . . . . ?
C5A C6A C7A C2A -0.1(4) . . . . ?
C7A C2A C3A C4A 1.2(4) . . . . ?
C8A C9A C10A C11A 170.3(2) . . . . ?
C9A N1A C1A O1A -1.4(4) . . . . ?
C9A N1A C1A C2A 178.8(2) . . . . ?
C9A C10A C11A C12A -91.8(3) . . . . ?
C9A C10A C11A C16A 87.6(3) . . . . ?
C10A C11A C12A C13A 178.4(3) . . . . ?
C10A C11A C16A C15A -177.4(2) . . . . ?
C11A C12A C13A C14A -0.6(4) . . . . ?
C12A C11A C16A C15A 2.0(4) . . . . ?
C12A C13A C14A C15A 1.2(4) . . . . ?
C13A C14A C15A C16A -0.3(4) . . . . ?
C14A C15A C16A C11A -1.4(4) . . . . ?
C16A C11A C12A C13A -1.1(4) . . . . ?
Cl1B C5B C6B C7B 178.4(2) . . . . ?
O1B C1B C2B C3B -21.2(4) . . . . ?
O1B C1B C2B C7B 158.4(3) . . . . ?
O2B C8B C9B N1B -152.4(2) . . . . ?
O2B C8B C9B C10B 86.2(3) . . . . ?
O3B C8B C9B N1B 30.5(4) . . . . ?
O3B C8B C9B C10B -90.9(3) . . . . ?
N1B C1B C2B C3B 159.1(2) . . . . ?
N1B C1B C2B C7B -21.3(4) . . . . ?
N1B C9B C10B C11B 85.0(3) . . . . ?
C1B N1B C9B C8B 63.4(3) . . . . ?
C1B N1B C9B C10B -176.8(2) . . . . ?
C1B C2B C3B C4B 179.4(3) . . . . ?
C1B C2B C7B C6B 179.8(3) . . . . ?
C2B C3B C4B C5B 0.6(4) . . . . ?
C3B C2B C7B C6B -0.6(4) . . . . ?
C3B C4B C5B Cl1B -179.2(2) . . . . ?
C3B C4B C5B C6B -0.1(4) . . . . ?
C4B C5B C6B C7B -0.7(4) . . . . ?
C5B C6B C7B C2B 1.1(4) . . . . ?
C7B C2B C3B C4B -0.2(4) . . . . ?
C8B C9B C10B C11B -153.8(2) . . . . ?
C9B N1B C1B O1B -0.2(4) . . . . ?
C9B N1B C1B C2B 179.5(2) . . . . ?
C9B C10B C11B C12B -60.8(3) . . . . ?
C9B C10B C11B C13B 176.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
####################################################################### 
# 
# 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_22kaw21_a
_database_code_depnum_ccdc_archive 'CCDC 2312811'
loop_
_audit_author_name
_audit_author_address
'Kraig Wheeler'
;Whitworth University
United States of America
;
_audit_update_record             
;
2023-12-18 deposited with the CCDC.	2024-02-12 downloaded from the CCDC.
;
_audit_creation_date             2023-12-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H15 N O3'
_chemical_formula_sum            'C16 H15 N O3'
_chemical_formula_weight         269.29
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   11.2259(5)
_cell_length_b                   9.0079(4)
_cell_length_c                   14.0101(6)
_cell_angle_alpha                90
_cell_angle_beta                 107.0970(10)
_cell_angle_gamma                90
_cell_volume                     1354.12(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9909
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.25
_cell_measurement_theta_min      6.42
_shelx_estimated_absorpt_T_max   0.964
_shelx_estimated_absorpt_T_min   0.864
_exptl_absorpt_coefficient_mu    0.748
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.201
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.049
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0145
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            23025
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.239
_diffrn_reflns_theta_min         5.920
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'κ-geometry four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'focusing mirror'
_diffrn_radiation_detector       'Bruker PHOTON II'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2616
_reflns_number_total             2643
_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       'SAINT+ V8.40B (Bruker AXS Inc., 2020)'
_computing_data_collection       'APEX5 Ver.2022.08-RC130 (Bruker-AXS, 2023)'
_computing_data_reduction        'SAINT+ Ve8.40B (Bruker-AXS, 2020)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2019/1)'
_computing_structure_solution    'XT (Sheldrick, 2018/2)'
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2643
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0321
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0353P)²+0.5826P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0794
_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron  density map and refined using anisotropic displacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv of the connected C atoms (1.5xUeqiv for methyl groups). Those H atoms
 attached to nitrogen and oxygen were located in Fourier diff maps and assigned Uiso = 1.2xUeqiv for nitrogen (1.5xUeqiv for oxygen).
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16)
;
_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 0.46680(7) 0.19288(8) 0.33701(5) 0.01873(17) Uani 1 1 d . . . . .
O2 O 0.64392(7) 0.49539(9) 0.29195(6) 0.02185(18) Uani 1 1 d . . . . .
H2 H 0.6048(13) 0.5614(16) 0.2449(11) 0.026 Uiso 1 1 d . U . . .
O3 O 0.48408(6) 0.53680(8) 0.35332(5) 0.01714(17) Uani 1 1 d . . . . .
N1 N 0.56241(8) 0.29883(9) 0.48411(6) 0.01470(18) Uani 1 1 d . . . . .
H1 H 0.5536(11) 0.3333(14) 0.5394(10) 0.018 Uiso 1 1 d . U . . .
C1 C 0.47244(9) 0.21287(11) 0.42593(7) 0.0147(2) Uani 1 1 d . . . . .
C2 C 0.38099(9) 0.14564(11) 0.47209(7) 0.0157(2) Uani 1 1 d . . . . .
C3 C 0.26744(10) 0.09494(12) 0.40949(8) 0.0202(2) Uani 1 1 d . . . . .
H3 H 0.250030 0.103536 0.339133 0.024 Uiso 1 1 calc R U . . .
C4 C 0.17980(10) 0.03207(13) 0.44930(9) 0.0243(2) Uani 1 1 d . . . . .
H4 H 0.102463 -0.001765 0.406262 0.029 Uiso 1 1 calc R U . . .
C5 C 0.20498(10) 0.01859(12) 0.55179(9) 0.0233(2) Uani 1 1 d . . . . .
H5 H 0.145021 -0.024920 0.578980 0.028 Uiso 1 1 calc R U . . .
C6 C 0.31779(10) 0.06861(12) 0.61492(8) 0.0221(2) Uani 1 1 d . . . . .
H6 H 0.334782 0.059476 0.685208 0.026 Uiso 1 1 calc R U . . .
C7 C 0.40576(10) 0.13195(11) 0.57538(8) 0.0185(2) Uani 1 1 d . . . . .
H7 H 0.482876 0.165994 0.618657 0.022 Uiso 1 1 calc R U . . .
C8 C 0.58177(9) 0.47581(11) 0.35698(7) 0.0150(2) Uani 1 1 d . . . . .
C9 C 0.65027(9) 0.37246(11) 0.44206(7) 0.0152(2) Uani 1 1 d . . . . .
H9 H 0.697128 0.296098 0.415741 0.018 Uiso 1 1 calc R U . . .
C10 C 0.74326(9) 0.46628(11) 0.52249(7) 0.0177(2) Uani 1 1 d . . . . .
H10A H 0.790002 0.531558 0.489347 0.021 Uiso 1 1 calc R U . . .
H10B H 0.695782 0.530771 0.555487 0.021 Uiso 1 1 calc R U . . .
C11 C 0.83560(9) 0.37559(11) 0.60168(7) 0.0170(2) Uani 1 1 d . . . . .
C12 C 0.95414(10) 0.34739(12) 0.59307(8) 0.0213(2) Uani 1 1 d . . . . .
H12 H 0.975368 0.382568 0.536246 0.026 Uiso 1 1 calc R U . . .
C13 C 1.04177(10) 0.26850(13) 0.66647(9) 0.0252(2) Uani 1 1 d . . . . .
H13 H 1.122921 0.252553 0.660480 0.030 Uiso 1 1 calc R U . . .
C14 C 1.01073(11) 0.21330(13) 0.74814(9) 0.0262(3) Uani 1 1 d . . . . .
H14 H 1.070024 0.158308 0.797960 0.031 Uiso 1 1 calc R U . . .
C15 C 0.89275(11) 0.23865(13) 0.75686(8) 0.0254(2) Uani 1 1 d . . . . .
H15 H 0.870867 0.199680 0.812446 0.031 Uiso 1 1 calc R U . . .
C16 C 0.80594(10) 0.32079(12) 0.68484(8) 0.0209(2) Uani 1 1 d . . . . .
H16 H 0.725953 0.339588 0.692438 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 C1 1.2418(12) . ?
O2 H2 0.901(15) . ?
O2 C8 1.3121(12) . ?
O3 C8 1.2142(12) . ?
N1 H1 0.867(13) . ?
N1 C1 1.3416(13) . ?
N1 C9 1.4496(12) . ?
C1 C2 1.4931(14) . ?
C2 C3 1.3948(14) . ?
C2 C7 1.3963(14) . ?
C3 H3 0.9500 . ?
C3 C4 1.3864(15) . ?
C4 H4 0.9500 . ?
C4 C5 1.3848(16) . ?
C5 H5 0.9500 . ?
C5 C6 1.3894(16) . ?
C6 H6 0.9500 . ?
C6 C7 1.3890(15) . ?
C7 H7 0.9500 . ?
C8 C9 1.5296(13) . ?
C9 H9 1.0000 . ?
C9 C10 1.5434(13) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5154(14) . ?
C11 C12 1.3944(15) . ?
C11 C16 1.3928(15) . ?
C12 H12 0.9500 . ?
C12 C13 1.3912(16) . ?
C13 H13 0.9500 . ?
C13 C14 1.3828(17) . ?
C14 H14 0.9500 . ?
C14 C15 1.3844(17) . ?
C15 H15 0.9500 . ?
C15 C16 1.3918(15) . ?
C16 H16 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
C8 O2 H2 110.7(9) . . ?
C1 N1 H1 119.1(8) . . ?
C1 N1 C9 119.85(8) . . ?
C9 N1 H1 118.0(8) . . ?
O1 C1 N1 120.03(9) . . ?
O1 C1 C2 122.48(9) . . ?
N1 C1 C2 117.48(8) . . ?
C3 C2 C1 118.56(9) . . ?
C3 C2 C7 119.30(9) . . ?
C7 C2 C1 122.14(9) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.41(10) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.02(10) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.10(10) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 120.08(10) . . ?
C7 C6 H6 120.0 . . ?
C2 C7 H7 120.0 . . ?
C6 C7 C2 120.08(10) . . ?
C6 C7 H7 120.0 . . ?
O2 C8 C9 112.01(8) . . ?
O3 C8 O2 124.60(9) . . ?
O3 C8 C9 123.31(9) . . ?
N1 C9 C8 110.42(8) . . ?
N1 C9 H9 109.2 . . ?
N1 C9 C10 110.41(8) . . ?
C8 C9 H9 109.2 . . ?
C8 C9 C10 108.23(8) . . ?
C10 C9 H9 109.2 . . ?
C9 C10 H10A 108.7 . . ?
C9 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C11 C10 C9 114.18(8) . . ?
C11 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C12 C11 C10 119.97(9) . . ?
C16 C11 C10 121.54(9) . . ?
C16 C11 C12 118.47(9) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 120.97(10) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 119.99(10) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 120.2 . . ?
C13 C14 C15 119.61(10) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 H15 119.7 . . ?
C14 C15 C16 120.52(11) . . ?
C16 C15 H15 119.7 . . ?
C11 C16 H16 119.8 . . ?
C15 C16 C11 120.41(10) . . ?
C15 C16 H16 119.8 . . ?

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
O2 H2 O1 0.901(15) 1.680(15) 2.5795(10) 176.3(13) 2_655 yes
N1 H1 O3 0.867(13) 2.045(14) 2.8898(11) 164.7(12) 3_666 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
O1 C1 C2 C3 -18.50(14) . . . . ?
O1 C1 C2 C7 161.41(10) . . . . ?
O2 C8 C9 N1 -153.43(8) . . . . ?
O2 C8 C9 C10 85.60(10) . . . . ?
O3 C8 C9 N1 29.53(13) . . . . ?
O3 C8 C9 C10 -91.44(11) . . . . ?
N1 C1 C2 C3 160.83(9) . . . . ?
N1 C1 C2 C7 -19.27(14) . . . . ?
N1 C9 C10 C11 70.43(11) . . . . ?
C1 N1 C9 C8 59.54(11) . . . . ?
C1 N1 C9 C10 179.19(8) . . . . ?
C1 C2 C3 C4 -179.86(9) . . . . ?
C1 C2 C7 C6 180.00(9) . . . . ?
C2 C3 C4 C5 -0.33(17) . . . . ?
C3 C2 C7 C6 -0.10(15) . . . . ?
C3 C4 C5 C6 0.29(17) . . . . ?
C4 C5 C6 C7 -0.16(17) . . . . ?
C5 C6 C7 C2 0.06(16) . . . . ?
C7 C2 C3 C4 0.23(15) . . . . ?
C8 C9 C10 C11 -168.60(8) . . . . ?
C9 N1 C1 O1 2.17(14) . . . . ?
C9 N1 C1 C2 -177.17(8) . . . . ?
C9 C10 C11 C12 96.56(11) . . . . ?
C9 C10 C11 C16 -84.51(12) . . . . ?
C10 C11 C12 C13 177.91(10) . . . . ?
C10 C11 C16 C15 -179.55(10) . . . . ?
C11 C12 C13 C14 1.77(17) . . . . ?
C12 C11 C16 C15 -0.60(16) . . . . ?
C12 C13 C14 C15 -0.80(17) . . . . ?
C13 C14 C15 C16 -0.85(17) . . . . ?
C14 C15 C16 C11 1.56(17) . . . . ?
C16 C11 C12 C13 -1.05(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
####################################################################### 
# 
# 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_22kaw17_a
_database_code_depnum_ccdc_archive 'CCDC 2312805'
loop_
_audit_author_name
_audit_author_address
'Kraig Wheeler'
;Whitworth University
United States of America
;
_audit_update_record             
;
2023-12-18 deposited with the CCDC.	2024-02-12 downloaded from the CCDC.
;
_audit_creation_date             2023-12-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H19 N O3, C17 H17 N O3'
_chemical_formula_sum            'C31 H36 N2 O6'
_chemical_formula_weight         532.62
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.6827(8)
_cell_length_b                   9.9438(8)
_cell_length_c                   14.4410(11)
_cell_angle_alpha                90
_cell_angle_beta                 110.660(3)
_cell_angle_gamma                90
_cell_volume                     1435.37(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9755
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.11
_cell_measurement_theta_min      3.27
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.694
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6372
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.231
_exptl_crystal_size_mid          0.207
_exptl_crystal_size_min          0.087
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            24786
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.271
_diffrn_reflns_theta_min         3.271
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'κ-geometry four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'focusing mirror'
_diffrn_radiation_detector       'Bruker PHOTON II'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.824
_reflns_Friedel_fraction_full    0.947
_reflns_Friedel_fraction_max     0.927
_reflns_number_gt                5281
_reflns_number_total             5455
_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       'SAINT+ V8.40B (Bruker AXS Inc., 2020)'
_computing_data_collection       'APEX5 Ver.2022.08-RC130 (Bruker-AXS, 2023)'
_computing_data_reduction        'SAINT+ Ve8.40B (Bruker-AXS, 2020)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2019/1)'
_computing_structure_solution    'XT (Sheldrick, 2018/2)'
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 2298 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(6)
_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     368
_refine_ls_number_reflns         5455
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0364
_refine_ls_restrained_S_all      1.053
_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)+(0.0615P)²+0.3397P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1003
_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier 
electron density map and refined using anisotropic displacement 
parameters. All C-H hydrogen atoms were placed in calculated 
positions with Uiso = 1.2xUeqiv of the connected C atoms 
(1.5xUeqiv for methyl groups). Those H atoms attached to nitrogen 
and oxygen were located in Fourier diff mapsand assigned Uiso = 
1.2xUeqiv for NH groups (Uiso = 1.5xUeqiv for OH groups).
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 N1B-H1B = O2B-H2B = O2A-H2A = N1A-H1A
 0.85 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C9A(H9A), C11A(H11A), C9B(H9B)
3.b Secondary CH2 refined with riding coordinates:
 C10A(H10C,H10D), C10B(H10A,H10B)
3.c Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C4A(H4A), C6A(H6A), C7A(H7A), C3B(H3B), C4B(H4B), C6B(H6B),
 C7B(H7B), C12B(H12B), C13B(H13B), C14B(H14B), C15B(H15B), C16B(H16B)
3.d Idealised Me refined as rotating group:
 C12A(H12A,H12C,H12D), C13A(H13A,H13C,H13D), C14A(H14A,H14C,H14D), C17B(H17A,
 H17B,H17C)
;
_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 0.90879(17) 0.22499(18) 0.41419(12) 0.0258(4) Uani 1 1 d . . . . .
O2A O 1.08674(16) 0.5447(2) 0.45592(12) 0.0276(4) Uani 1 1 d D . . . .
H2A H 1.078(3) 0.604(3) 0.501(2) 0.041 Uiso 1 1 d D U . . .
O3A O 0.86279(15) 0.55005(18) 0.40208(11) 0.0241(4) Uani 1 1 d . . . . .
N1A N 0.8556(2) 0.3397(2) 0.27185(13) 0.0223(4) Uani 1 1 d D . . . .
H1A H 0.795(2) 0.365(3) 0.2174(18) 0.027 Uiso 1 1 d D U . . .
C1A C 0.8294(2) 0.2441(2) 0.32788(15) 0.0214(5) Uani 1 1 d . . . . .
C2A C 0.7041(2) 0.1645(2) 0.28230(16) 0.0211(5) Uani 1 1 d . . . . .
C3A C 0.6486(2) 0.0959(3) 0.34243(16) 0.0262(5) Uani 1 1 d . . . . .
H3A H 0.691031 0.099332 0.412320 0.031 Uiso 1 1 calc R U . . .
C4A C 0.5318(2) 0.0226(3) 0.30113(18) 0.0292(5) Uani 1 1 d . . . . .
H4A H 0.495264 -0.024060 0.343161 0.035 Uiso 1 1 calc R U . . .
C5A C 0.4671(2) 0.0162(3) 0.19913(17) 0.0252(5) Uani 1 1 d . . . . .
C6A C 0.5234(2) 0.0842(2) 0.13928(16) 0.0254(5) Uani 1 1 d . . . . .
H6A H 0.480347 0.081155 0.069436 0.031 Uiso 1 1 calc R U . . .
C7A C 0.6408(2) 0.1560(2) 0.17957(16) 0.0233(5) Uani 1 1 d . . . . .
H7A H 0.678854 0.199836 0.137305 0.028 Uiso 1 1 calc R U . . .
C8A C 0.9666(2) 0.5118(2) 0.39506(15) 0.0205(5) Uani 1 1 d . . . . .
C9A C 0.9737(2) 0.4238(2) 0.31057(16) 0.0223(5) Uani 1 1 d . . . . .
H9A H 1.054459 0.364713 0.335989 0.027 Uiso 1 1 calc R U . . .
C10A C 0.9884(2) 0.5161(3) 0.22915(16) 0.0245(5) Uani 1 1 d . . . . .
H10C H 0.898210 0.548239 0.187794 0.029 Uiso 1 1 calc R U . . .
H10D H 1.041332 0.595895 0.261413 0.029 Uiso 1 1 calc R U . . .
C11A C 1.0541(3) 0.4535(3) 0.16097(17) 0.0346(6) Uani 1 1 d . . . . .
H11A H 1.144477 0.419374 0.202733 0.041 Uiso 1 1 calc R U . . .
C12A C 1.0729(3) 0.5652(3) 0.0918(2) 0.0430(7) Uani 1 1 d . . . . .
H12A H 1.124871 0.529486 0.053313 0.064 Uiso 1 1 calc R U . . .
H12C H 1.120463 0.641528 0.131657 0.064 Uiso 1 1 calc R U . . .
H12D H 0.985079 0.594919 0.046630 0.064 Uiso 1 1 calc R U . . .
C13A C 0.9755(4) 0.3382(3) 0.0994(2) 0.0463(7) Uani 1 1 d . . . . .
H13A H 0.973990 0.263012 0.142884 0.069 Uiso 1 1 calc R U . . .
H13C H 1.017755 0.309189 0.052562 0.069 Uiso 1 1 calc R U . . .
H13D H 0.883680 0.367593 0.062856 0.069 Uiso 1 1 calc R U . . .
C14A C 0.3400(2) -0.0641(3) 0.15210(19) 0.0329(6) Uani 1 1 d . . . . .
H14A H 0.322301 -0.118232 0.202864 0.049 Uiso 1 1 calc R U . . .
H14C H 0.350468 -0.123595 0.101188 0.049 Uiso 1 1 calc R U . . .
H14D H 0.265015 -0.002612 0.121805 0.049 Uiso 1 1 calc R U . . .
O1B O 0.59474(16) 0.76980(17) 0.07879(11) 0.0225(3) Uani 1 1 d . . . . .
O2B O 0.41224(15) 0.44218(19) 0.06029(11) 0.0267(4) Uani 1 1 d D . . . .
H2B H 0.411(3) 0.389(3) 0.014(2) 0.040 Uiso 1 1 d D U . . .
O3B O 0.63514(15) 0.45070(17) 0.10145(10) 0.0215(3) Uani 1 1 d . . . . .
N1B N 0.64934(18) 0.6664(2) 0.22596(13) 0.0194(4) Uani 1 1 d D . . . .
H1B H 0.713(2) 0.642(3) 0.2810(17) 0.023 Uiso 1 1 d D U . . .
C1B C 0.6748(2) 0.7550(2) 0.16480(15) 0.0187(4) Uani 1 1 d . . . . .
C2B C 0.8025(2) 0.8323(2) 0.20585(16) 0.0202(5) Uani 1 1 d . . . . .
C3B C 0.8594(2) 0.8866(3) 0.14148(17) 0.0259(5) Uani 1 1 d . . . . .
H3B H 0.817558 0.872885 0.072253 0.031 Uiso 1 1 calc R U . . .
C4B C 0.9769(2) 0.9610(3) 0.17726(18) 0.0289(5) Uani 1 1 d . . . . .
H4B H 1.014300 0.998130 0.132200 0.035 Uiso 1 1 calc R U . . .
C5B C 1.0405(2) 0.9818(3) 0.27879(18) 0.0265(5) Uani 1 1 d . . . . .
C6B C 0.9848(2) 0.9239(3) 0.34298(17) 0.0262(5) Uani 1 1 d . . . . .
H6B H 1.028329 0.934799 0.412342 0.031 Uiso 1 1 calc R U . . .
C7B C 0.8671(2) 0.8507(2) 0.30781(16) 0.0228(5) Uani 1 1 d . . . . .
H7B H 0.830144 0.812993 0.352908 0.027 Uiso 1 1 calc R U . . .
C8B C 0.5335(2) 0.4852(2) 0.11336(15) 0.0192(5) Uani 1 1 d . . . . .
C9B C 0.5291(2) 0.5849(2) 0.19279(15) 0.0203(5) Uani 1 1 d . . . . .
H9B H 0.450060 0.645330 0.163785 0.024 Uiso 1 1 calc R U . . .
C10B C 0.5146(2) 0.5103(3) 0.28234(16) 0.0232(5) Uani 1 1 d . . . . .
H10A H 0.440633 0.444443 0.258527 0.028 Uiso 1 1 calc R U . . .
H10B H 0.598038 0.460038 0.317179 0.028 Uiso 1 1 calc R U . . .
C11B C 0.4868(2) 0.6067(2) 0.35417(16) 0.0225(5) Uani 1 1 d . . . . .
C12B C 0.5897(2) 0.6640(3) 0.43298(16) 0.0281(5) Uani 1 1 d . . . . .
H12B H 0.679958 0.640056 0.444299 0.034 Uiso 1 1 calc R U . . .
C13B C 0.5606(3) 0.7561(3) 0.49510(17) 0.0326(6) Uani 1 1 d . . . . .
H13B H 0.631380 0.795630 0.548030 0.039 Uiso 1 1 calc R U . . .
C14B C 0.4297(3) 0.7907(3) 0.48053(18) 0.0327(6) Uani 1 1 d . . . . .
H14B H 0.410573 0.853888 0.523075 0.039 Uiso 1 1 calc R U . . .
C15B C 0.3268(3) 0.7327(3) 0.4035(2) 0.0341(6) Uani 1 1 d . . . . .
H15B H 0.236484 0.755368 0.393411 0.041 Uiso 1 1 calc R U . . .
C16B C 0.3555(2) 0.6416(3) 0.34115(19) 0.0304(5) Uani 1 1 d . . . . .
H16B H 0.284248 0.602196 0.288514 0.036 Uiso 1 1 calc R U . . .
C17B C 1.1647(3) 1.0670(3) 0.3185(2) 0.0348(6) Uani 1 1 d . . . . .
H17A H 1.154839 1.130762 0.367246 0.052 Uiso 1 1 calc R U . . .
H17B H 1.177841 1.116645 0.264012 0.052 Uiso 1 1 calc R U . . .
H17C H 1.242338 1.009097 0.350154 0.052 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
O1A C1A 1.250(3) . ?
O2A H2A 0.90(2) . ?
O2A C8A 1.315(3) . ?
O3A C8A 1.210(3) . ?
N1A H1A 0.86(2) . ?
N1A C1A 1.341(3) . ?
N1A C9A 1.451(3) . ?
C1A C2A 1.493(3) . ?
C2A C3A 1.391(3) . ?
C2A C7A 1.399(3) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.385(4) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.390(3) . ?
C5A C6A 1.390(3) . ?
C5A C14A 1.514(3) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.381(3) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.525(3) . ?
C9A H9A 1.0000 . ?
C9A C10A 1.543(3) . ?
C10A H10C 0.9900 . ?
C10A H10D 0.9900 . ?
C10A C11A 1.529(3) . ?
C11A H11A 1.0000 . ?
C11A C12A 1.553(4) . ?
C11A C13A 1.512(4) . ?
C12A H12A 0.9800 . ?
C12A H12C 0.9800 . ?
C12A H12D 0.9800 . ?
C13A H13A 0.9800 . ?
C13A H13C 0.9800 . ?
C13A H13D 0.9800 . ?
C14A H14A 0.9800 . ?
C14A H14C 0.9800 . ?
C14A H14D 0.9800 . ?
O1B C1B 1.243(3) . ?
O2B H2B 0.85(2) . ?
O2B C8B 1.322(3) . ?
O3B C8B 1.207(3) . ?
N1B H1B 0.88(2) . ?
N1B C1B 1.341(3) . ?
N1B C9B 1.450(3) . ?
C1B C2B 1.495(3) . ?
C2B C3B 1.387(3) . ?
C2B C7B 1.400(3) . ?
C3B H3B 0.9500 . ?
C3B C4B 1.391(3) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.397(3) . ?
C5B C6B 1.391(4) . ?
C5B C17B 1.507(3) . ?
C6B H6B 0.9500 . ?
C6B C7B 1.385(3) . ?
C7B H7B 0.9500 . ?
C8B C9B 1.529(3) . ?
C9B H9B 1.0000 . ?
C9B C10B 1.545(3) . ?
C10B H10A 0.9900 . ?
C10B H10B 0.9900 . ?
C10B C11B 1.517(3) . ?
C11B C12B 1.395(3) . ?
C11B C16B 1.391(3) . ?
C12B H12B 0.9500 . ?
C12B C13B 1.392(3) . ?
C13B H13B 0.9500 . ?
C13B C14B 1.382(4) . ?
C14B H14B 0.9500 . ?
C14B C15B 1.384(4) . ?
C15B H15B 0.9500 . ?
C15B C16B 1.387(4) . ?
C16B H16B 0.9500 . ?
C17B H17A 0.9800 . ?
C17B H17B 0.9800 . ?
C17B H17C 0.9800 . ?

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
C8A O2A H2A 109(2) . . ?
C1A N1A H1A 120(2) . . ?
C1A N1A C9A 120.98(18) . . ?
C9A N1A H1A 117(2) . . ?
O1A C1A N1A 119.8(2) . . ?
O1A C1A C2A 123.1(2) . . ?
N1A C1A C2A 117.11(19) . . ?
C3A C2A C1A 119.87(19) . . ?
C3A C2A C7A 118.6(2) . . ?
C7A C2A C1A 121.5(2) . . ?
C2A C3A H3A 119.8 . . ?
C4A C3A C2A 120.5(2) . . ?
C4A C3A H3A 119.8 . . ?
C3A C4A H4A 119.5 . . ?
C3A C4A C5A 121.0(2) . . ?
C5A C4A H4A 119.5 . . ?
C4A C5A C14A 122.1(2) . . ?
C6A C5A C4A 118.3(2) . . ?
C6A C5A C14A 119.6(2) . . ?
C5A C6A H6A 119.4 . . ?
C7A C6A C5A 121.2(2) . . ?
C7A C6A H6A 119.4 . . ?
C2A C7A H7A 119.8 . . ?
C6A C7A C2A 120.3(2) . . ?
C6A C7A H7A 119.8 . . ?
O2A C8A C9A 111.42(18) . . ?
O3A C8A O2A 124.9(2) . . ?
O3A C8A C9A 123.59(19) . . ?
N1A C9A C8A 110.92(18) . . ?
N1A C9A H9A 108.9 . . ?
N1A C9A C10A 110.95(17) . . ?
C8A C9A H9A 108.9 . . ?
C8A C9A C10A 108.4(2) . . ?
C10A C9A H9A 108.9 . . ?
C9A C10A H10C 108.2 . . ?
C9A C10A H10D 108.2 . . ?
H10C C10A H10D 107.4 . . ?
C11A C10A C9A 116.2(2) . . ?
C11A C10A H10C 108.2 . . ?
C11A C10A H10D 108.2 . . ?
C10A C11A H11A 108.4 . . ?
C10A C11A C12A 108.4(2) . . ?
C12A C11A H11A 108.4 . . ?
C13A C11A C10A 113.7(2) . . ?
C13A C11A H11A 108.4 . . ?
C13A C11A C12A 109.6(2) . . ?
C11A C12A H12A 109.5 . . ?
C11A C12A H12C 109.5 . . ?
C11A C12A H12D 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12A C12A H12D 109.5 . . ?
H12C C12A H12D 109.5 . . ?
C11A C13A H13A 109.5 . . ?
C11A C13A H13C 109.5 . . ?
C11A C13A H13D 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13A C13A H13D 109.5 . . ?
H13C C13A H13D 109.5 . . ?
C5A C14A H14A 109.5 . . ?
C5A C14A H14C 109.5 . . ?
C5A C14A H14D 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14A C14A H14D 109.5 . . ?
H14C C14A H14D 109.5 . . ?
C8B O2B H2B 113(2) . . ?
C1B N1B H1B 120.4(19) . . ?
C1B N1B C9B 120.76(18) . . ?
C9B N1B H1B 117.2(19) . . ?
O1B C1B N1B 120.5(2) . . ?
O1B C1B C2B 123.0(2) . . ?
N1B C1B C2B 116.44(18) . . ?
C3B C2B C1B 119.27(19) . . ?
C3B C2B C7B 118.9(2) . . ?
C7B C2B C1B 121.8(2) . . ?
C2B C3B H3B 119.7 . . ?
C2B C3B C4B 120.7(2) . . ?
C4B C3B H3B 119.7 . . ?
C3B C4B H4B 119.7 . . ?
C3B C4B C5B 120.7(2) . . ?
C5B C4B H4B 119.7 . . ?
C4B C5B C17B 121.3(2) . . ?
C6B C5B C4B 118.3(2) . . ?
C6B C5B C17B 120.4(2) . . ?
C5B C6B H6B 119.3 . . ?
C7B C6B C5B 121.3(2) . . ?
C7B C6B H6B 119.3 . . ?
C2B C7B H7B 120.0 . . ?
C6B C7B C2B 120.1(2) . . ?
C6B C7B H7B 120.0 . . ?
O2B C8B C9B 111.14(18) . . ?
O3B C8B O2B 124.9(2) . . ?
O3B C8B C9B 124.0(2) . . ?
N1B C9B C8B 110.58(18) . . ?
N1B C9B H9B 108.7 . . ?
N1B C9B C10B 109.29(17) . . ?
C8B C9B H9B 108.7 . . ?
C8B C9B C10B 110.83(18) . . ?
C10B C9B H9B 108.7 . . ?
C9B C10B H10A 109.3 . . ?
C9B C10B H10B 109.3 . . ?
H10A C10B H10B 107.9 . . ?
C11B C10B C9B 111.74(19) . . ?
C11B C10B H10A 109.3 . . ?
C11B C10B H10B 109.3 . . ?
C12B C11B C10B 121.8(2) . . ?
C16B C11B C10B 119.8(2) . . ?
C16B C11B C12B 118.4(2) . . ?
C11B C12B H12B 119.9 . . ?
C13B C12B C11B 120.3(2) . . ?
C13B C12B H12B 119.9 . . ?
C12B C13B H13B 119.7 . . ?
C14B C13B C12B 120.6(2) . . ?
C14B C13B H13B 119.7 . . ?
C13B C14B H14B 120.2 . . ?
C13B C14B C15B 119.6(2) . . ?
C15B C14B H14B 120.2 . . ?
C14B C15B H15B 120.0 . . ?
C14B C15B C16B 119.9(2) . . ?
C16B C15B H15B 120.0 . . ?
C11B C16B H16B 119.4 . . ?
C15B C16B C11B 121.3(2) . . ?
C15B C16B H16B 119.4 . . ?
C5B C17B H17A 109.5 . . ?
C5B C17B H17B 109.5 . . ?
C5B C17B H17C 109.5 . . ?
H17A C17B H17B 109.5 . . ?
H17A C17B H17C 109.5 . . ?
H17B C17B H17C 109.5 . . ?

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
O2A H2A O1A 0.90(2) 1.69(2) 2.583(2) 169(3) 2_756 yes
N1A H1A O3B 0.86(2) 2.10(2) 2.955(2) 170(3) . yes
O2B H2B O1B 0.85(2) 1.77(2) 2.621(2) 176(4) 2_645 yes
N1B H1B O3A 0.88(2) 2.12(2) 2.986(2) 170(3) . 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
O1A C1A C2A C3A 20.5(3) . . . . ?
O1A C1A C2A C7A -159.0(2) . . . . ?
O2A C8A C9A N1A 153.9(2) . . . . ?
O2A C8A C9A C10A -84.1(2) . . . . ?
O3A C8A C9A N1A -28.8(3) . . . . ?
O3A C8A C9A C10A 93.2(3) . . . . ?
N1A C1A C2A C3A -159.7(2) . . . . ?
N1A C1A C2A C7A 20.9(3) . . . . ?
N1A C9A C10A C11A -82.7(2) . . . . ?
C1A N1A C9A C8A -64.9(3) . . . . ?
C1A N1A C9A C10A 174.6(2) . . . . ?
C1A C2A C3A C4A 179.5(2) . . . . ?
C1A C2A C7A C6A -178.6(2) . . . . ?
C2A C3A C4A C5A -0.3(4) . . . . ?
C3A C2A C7A C6A 2.0(3) . . . . ?
C3A C4A C5A C6A 0.7(4) . . . . ?
C3A C4A C5A C14A 179.5(2) . . . . ?
C4A C5A C6A C7A 0.3(4) . . . . ?
C5A C6A C7A C2A -1.6(4) . . . . ?
C7A C2A C3A C4A -1.1(4) . . . . ?
C8A C9A C10A C11A 155.3(2) . . . . ?
C9A N1A C1A O1A -1.3(3) . . . . ?
C9A N1A C1A C2A 178.80(19) . . . . ?
C9A C10A C11A C12A -174.3(2) . . . . ?
C9A C10A C11A C13A 63.6(3) . . . . ?
C14A C5A C6A C7A -178.6(2) . . . . ?
O1B C1B C2B C3B -23.1(3) . . . . ?
O1B C1B C2B C7B 157.3(2) . . . . ?
O2B C8B C9B N1B -159.57(19) . . . . ?
O2B C8B C9B C10B 79.1(2) . . . . ?
O3B C8B C9B N1B 20.6(3) . . . . ?
O3B C8B C9B C10B -100.7(2) . . . . ?
N1B C1B C2B C3B 156.8(2) . . . . ?
N1B C1B C2B C7B -22.8(3) . . . . ?
N1B C9B C10B C11B 67.4(2) . . . . ?
C1B N1B C9B C8B 66.9(3) . . . . ?
C1B N1B C9B C10B -170.8(2) . . . . ?
C1B C2B C3B C4B 178.9(2) . . . . ?
C1B C2B C7B C6B -179.5(2) . . . . ?
C2B C3B C4B C5B 0.4(4) . . . . ?
C3B C2B C7B C6B 0.9(3) . . . . ?
C3B C4B C5B C6B 1.3(4) . . . . ?
C3B C4B C5B C17B -177.4(2) . . . . ?
C4B C5B C6B C7B -1.9(4) . . . . ?
C5B C6B C7B C2B 0.8(4) . . . . ?
C7B C2B C3B C4B -1.5(4) . . . . ?
C8B C9B C10B C11B -170.48(18) . . . . ?
C9B N1B C1B O1B 0.9(3) . . . . ?
C9B N1B C1B C2B -179.03(19) . . . . ?
C9B C10B C11B C12B -90.6(3) . . . . ?
C9B C10B C11B C16B 88.3(3) . . . . ?
C10B C11B C12B C13B 177.5(2) . . . . ?
C10B C11B C16B C15B -177.9(2) . . . . ?
C11B C12B C13B C14B 0.9(4) . . . . ?
C12B C11B C16B C15B 1.1(4) . . . . ?
C12B C13B C14B C15B 0.2(4) . . . . ?
C13B C14B C15B C16B -0.6(4) . . . . ?
C14B C15B C16B C11B -0.1(4) . . . . ?
C16B C11B C12B C13B -1.5(4) . . . . ?
C17B C5B C6B C7B 176.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
####################################################################### 
# 
# 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_21kaw58_a
_database_code_depnum_ccdc_archive 'CCDC 2312804'
loop_
_audit_author_name
_audit_author_address
'Kraig Wheeler'
;Whitworth University
United States of America
;
_audit_update_record             
;
2023-12-18 deposited with the CCDC.	2024-02-12 downloaded from the CCDC.
;
_audit_creation_date             2023-12-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H17 N O3, C16 H14 Cl N O3'
_chemical_formula_sum            'C33 H31 Cl N2 O6'
_chemical_formula_weight         587.05
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.8824(6)
_cell_length_b                   10.0217(6)
_cell_length_c                   14.4325(8)
_cell_angle_alpha                90
_cell_angle_beta                 111.003(2)
_cell_angle_gamma                90
_cell_volume                     1469.44(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9785
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.09
_cell_measurement_theta_min      4.41
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.551
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6355
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Blocks
_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
-1.00 -1.00 0.00 0.1110
0.00 0.00 1.00 0.0890
0.00 0.00 -1.00 0.0490
0.00 1.00 -1.00 0.2110
0.00 1.00 0.00 0.2520
1.00 -1.00 1.00 0.1350
1.00 0.00 1.00 0.1170
-1.00 0.00 -1.00 0.0630
1.00 -1.00 0.00 0.1540
-1.00 1.00 0.00 0.2110
1.00 1.00 1.00 0.2120
-1.00 -1.00 -1.00 0.1070
1.00 0.00 -1.00 0.0660
-1.00 0.00 1.00 0.0810
1.00 1.00 -1.00 0.1810
-1.00 -1.00 1.00 0.0940

_exptl_crystal_size_max          0.504
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.177
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            35012
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.079
_diffrn_reflns_theta_min         3.280
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'κ-geometry four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'focusing mirror'
_diffrn_radiation_detector       'Bruker PHOTON II'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.856
_reflns_Friedel_fraction_full    0.979
_reflns_Friedel_fraction_max     0.962
_reflns_number_gt                5610
_reflns_number_total             5686
_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       'SAINT+ V8.40B (Bruker AXS Inc., 2020)'
_computing_data_collection       'APEX5 Ver.2022.08-RC130 (Bruker-AXS, 2023)'
_computing_data_reduction        'SAINT+ Ve8.40B (Bruker-AXS, 2020)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2019/1)'
_computing_structure_solution    'XT (Sheldrick, 2018/2)'
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 2510 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.123(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     392
_refine_ls_number_reflns         5686
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0359
_refine_ls_restrained_S_all      1.069
_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)+(0.0421P)²+0.8159P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.0964
_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier 
electron density map and refined using anisotropic displacement 
parameters. All C-H hydrogen atoms were placed in calculated 
positions with Uiso = 1.2xUeqiv of the connected C atoms 
(1.5xUeqiv for methyl groups). Those H atoms attached to nitrogen 
and oxygen were located in Fourier diff mapsand assigned Uiso = 
1.2xUeqiv for NH groups (Uiso = 1.5xUeqiv for OH groups).
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9A(H9A), C9B(H9B)
2.b Secondary CH2 refined with riding coordinates:
 C10A(H10A,H10B), C10B(H10C,H10D)
2.c Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C4A(H4A), C6A(H6A), C7A(H7A), C12A(H12A), C13A(H13A), C14A(H14A),
 C15A(H15A), C16A(H16A), C3B(H3B), C4B(H4B), C6B(H6B), C7B(H7B), C12B(H12B),
 C13B(H13B), C14B(H14B), C15B(H15B), C16B(H16B)
2.d Idealised Me refined as rotating group:
 C17A(H17A,H17B,H17C)
;
_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 0.40212(19) 0.7814(2) 0.91892(14) 0.0193(4) Uani 1 1 d . . . . .
O2A O 0.58651(19) 0.4628(2) 0.95039(15) 0.0230(5) Uani 1 1 d . . . . .
H2A H 0.586(4) 0.397(5) 0.992(3) 0.034 Uiso 1 1 d . U . . .
O3A O 0.36605(18) 0.45681(19) 0.89905(14) 0.0184(4) Uani 1 1 d . . . . .
N1A N 0.3528(2) 0.6735(2) 0.77437(18) 0.0149(5) Uani 1 1 d . . . . .
H1A H 0.295(3) 0.654(4) 0.723(3) 0.018 Uiso 1 1 d . U . . .
C1A C 0.3249(3) 0.7641(3) 0.8324(2) 0.0151(5) Uani 1 1 d . . . . .
C2A C 0.1996(3) 0.8405(3) 0.7868(2) 0.0150(5) Uani 1 1 d . . . . .
C3A C 0.1481(3) 0.9098(3) 0.84889(19) 0.0190(6) Uani 1 1 d . . . . .
H3A H 0.192390 0.906860 0.918799 0.023 Uiso 1 1 calc R U . . .
C4A C 0.0323(3) 0.9830(3) 0.8087(2) 0.0221(6) Uani 1 1 d . . . . .
H4A H -0.001293 1.030270 0.851518 0.027 Uiso 1 1 calc R U . . .
C5A C -0.0348(3) 0.9879(3) 0.7065(2) 0.0183(6) Uani 1 1 d . . . . .
C6A C 0.0159(3) 0.9171(3) 0.64539(19) 0.0184(5) Uani 1 1 d . . . . .
H6A H -0.029995 0.917680 0.575641 0.022 Uiso 1 1 calc R U . . .
C7A C 0.1325(3) 0.8456(3) 0.6846(2) 0.0180(6) Uani 1 1 d . . . . .
H7A H 0.166746 0.799922 0.641477 0.022 Uiso 1 1 calc R U . . .
C8A C 0.4672(3) 0.4977(3) 0.89265(19) 0.0153(5) Uani 1 1 d . . . . .
C9A C 0.4730(3) 0.5956(3) 0.8126(2) 0.0152(5) Uani 1 1 d . . . . .
H9A H 0.549178 0.657447 0.842227 0.018 Uiso 1 1 calc R U . . .
C10A C 0.4928(3) 0.5172(3) 0.7270(2) 0.0170(6) Uani 1 1 d . . . . .
H10A H 0.565846 0.452868 0.754895 0.020 Uiso 1 1 calc R U . . .
H10B H 0.411940 0.465791 0.691307 0.020 Uiso 1 1 calc R U . . .
C11A C 0.5235(3) 0.6080(3) 0.6545(2) 0.0179(6) Uani 1 1 d . . . . .
C12A C 0.6523(3) 0.6513(3) 0.6745(2) 0.0232(6) Uani 1 1 d . . . . .
H12A H 0.720278 0.622646 0.733401 0.028 Uiso 1 1 calc R U . . .
C13A C 0.6826(3) 0.7358(3) 0.6095(3) 0.0284(7) Uani 1 1 d . . . . .
H13A H 0.770916 0.763832 0.623743 0.034 Uiso 1 1 calc R U . . .
C14A C 0.5841(4) 0.7791(3) 0.5239(3) 0.0294(7) Uani 1 1 d . . . . .
H14A H 0.604643 0.837153 0.479435 0.035 Uiso 1 1 calc R U . . .
C15A C 0.4554(3) 0.7376(4) 0.5030(2) 0.0291(7) Uani 1 1 d . . . . .
H15A H 0.387737 0.767805 0.444409 0.035 Uiso 1 1 calc R U . . .
C16A C 0.4252(3) 0.6517(3) 0.5677(2) 0.0237(6) Uani 1 1 d . . . . .
H16A H 0.337011 0.622783 0.552565 0.028 Uiso 1 1 calc R U . . .
C17A C -0.1592(3) 1.0697(3) 0.6618(2) 0.0239(6) Uani 1 1 d . . . . .
H17A H -0.153015 1.123737 0.607054 0.036 Uiso 1 1 calc R U . . .
H17B H -0.169868 1.128335 0.712701 0.036 Uiso 1 1 calc R U . . .
H17C H -0.235201 1.009795 0.636693 0.036 Uiso 1 1 calc R U . . .
Cl1B Cl 0.68080(7) -0.07100(9) 0.83629(6) 0.02969(18) Uani 1 1 d . . . . .
O1B O 0.09725(19) 0.2225(2) 0.58440(14) 0.0202(4) Uani 1 1 d . . . . .
O2B O -0.07764(19) 0.5508(2) 0.55502(15) 0.0221(5) Uani 1 1 d . . . . .
H2B H -0.076(4) 0.599(5) 0.509(3) 0.033 Uiso 1 1 d . U . . .
O3B O 0.14284(18) 0.54795(19) 0.60049(14) 0.0177(4) Uani 1 1 d . . . . .
N1B N 0.1551(2) 0.3351(3) 0.72775(18) 0.0170(5) Uani 1 1 d . . . . .
H1B H 0.219(3) 0.360(4) 0.784(3) 0.020 Uiso 1 1 d . U . . .
C1B C 0.1775(3) 0.2406(3) 0.6702(2) 0.0161(6) Uani 1 1 d . . . . .
C2B C 0.3014(3) 0.1611(3) 0.7128(2) 0.0158(6) Uani 1 1 d . . . . .
C3B C 0.3482(3) 0.0894(3) 0.6501(2) 0.0193(6) Uani 1 1 d . . . . .
H3B H 0.300064 0.089945 0.580670 0.023 Uiso 1 1 calc R U . . .
C4B C 0.4641(3) 0.0170(3) 0.6873(2) 0.0212(6) Uani 1 1 d . . . . .
H4B H 0.495387 -0.032008 0.643847 0.025 Uiso 1 1 calc R U . . .
C5B C 0.5337(3) 0.0170(3) 0.7885(2) 0.0186(6) Uani 1 1 d . . . . .
C6B C 0.4890(3) 0.0869(3) 0.8530(2) 0.0194(6) Uani 1 1 d . . . . .
H6B H 0.537954 0.086189 0.922323 0.023 Uiso 1 1 calc R U . . .
C7B C 0.3722(3) 0.1578(3) 0.8153(2) 0.0170(6) Uani 1 1 d . . . . .
H7B H 0.339854 0.204462 0.859221 0.020 Uiso 1 1 calc R U . . .
C8B C 0.0418(3) 0.5121(3) 0.6109(2) 0.0159(5) Uani 1 1 d . . . . .
C9B C 0.0374(2) 0.4158(3) 0.69173(19) 0.0180(6) Uani 1 1 d . . . . .
H9B H -0.039801 0.355155 0.662523 0.022 Uiso 1 1 calc R U . . .
C10B C 0.0196(3) 0.4921(3) 0.7783(2) 0.0196(6) Uani 1 1 d . . . . .
H10C H 0.101849 0.540582 0.815349 0.023 Uiso 1 1 calc R U . . .
H10D H -0.051530 0.558841 0.751704 0.023 Uiso 1 1 calc R U . . .
C11B C -0.0143(3) 0.3992(3) 0.8484(2) 0.0226(7) Uani 1 1 d . . . . .
C12B C -0.1443(3) 0.3590(3) 0.8267(3) 0.0270(7) Uani 1 1 d . . . . .
H12B H -0.211335 0.391998 0.768796 0.032 Uiso 1 1 calc R U . . .
C13B C -0.1774(3) 0.2702(3) 0.8893(3) 0.0300(7) Uani 1 1 d . . . . .
H13B H -0.266256 0.243804 0.874442 0.036 Uiso 1 1 calc R U . . .
C14B C -0.0792(4) 0.2217(3) 0.9728(3) 0.0306(7) Uani 1 1 d . . . . .
H14B H -0.100524 0.161938 1.015934 0.037 Uiso 1 1 calc R U . . .
C15B C 0.0497(4) 0.2597(4) 0.9937(2) 0.0311(7) Uani 1 1 d . . . . .
H15B H 0.116941 0.224949 1.050748 0.037 Uiso 1 1 calc R U . . .
C16B C 0.0821(3) 0.3486(3) 0.9321(2) 0.0272(7) Uani 1 1 d . . . . .
H16B H 0.171170 0.374602 0.947596 0.033 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
O1A C1A 1.243(3) . ?
O2A H2A 0.90(5) . ?
O2A C8A 1.314(3) . ?
O3A C8A 1.209(3) . ?
N1A H1A 0.81(4) . ?
N1A C1A 1.341(4) . ?
N1A C9A 1.451(3) . ?
C1A C2A 1.495(4) . ?
C2A C3A 1.400(4) . ?
C2A C7A 1.392(4) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.392(4) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.393(4) . ?
C5A C6A 1.390(4) . ?
C5A C17A 1.515(4) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.389(4) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.534(4) . ?
C9A H9A 1.0000 . ?
C9A C10A 1.543(4) . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C10A C11A 1.511(4) . ?
C11A C12A 1.395(4) . ?
C11A C16A 1.395(4) . ?
C12A H12A 0.9500 . ?
C12A C13A 1.388(5) . ?
C13A H13A 0.9500 . ?
C13A C14A 1.384(5) . ?
C14A H14A 0.9500 . ?
C14A C15A 1.386(5) . ?
C15A H15A 0.9500 . ?
C15A C16A 1.393(5) . ?
C16A H16A 0.9500 . ?
C17A H17A 0.9800 . ?
C17A H17B 0.9800 . ?
C17A H17C 0.9800 . ?
Cl1B C5B 1.739(3) . ?
O1B C1B 1.246(3) . ?
O2B H2B 0.83(4) . ?
O2B C8B 1.319(3) . ?
O3B C8B 1.216(3) . ?
N1B H1B 0.89(4) . ?
N1B C1B 1.338(4) . ?
N1B C9B 1.445(4) . ?
C1B C2B 1.497(4) . ?
C2B C3B 1.387(4) . ?
C2B C7B 1.402(4) . ?
C3B H3B 0.9500 . ?
C3B C4B 1.386(4) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.384(4) . ?
C5B C6B 1.384(4) . ?
C6B H6B 0.9500 . ?
C6B C7B 1.387(4) . ?
C7B H7B 0.9500 . ?
C8B C9B 1.528(4) . ?
C9B H9B 1.0000 . ?
C9B C10B 1.535(4) . ?
C10B H10C 0.9900 . ?
C10B H10D 0.9900 . ?
C10B C11B 1.515(4) . ?
C11B C12B 1.394(4) . ?
C11B C16B 1.382(5) . ?
C12B H12B 0.9500 . ?
C12B C13B 1.404(5) . ?
C13B H13B 0.9500 . ?
C13B C14B 1.381(5) . ?
C14B H14B 0.9500 . ?
C14B C15B 1.379(5) . ?
C15B H15B 0.9500 . ?
C15B C16B 1.391(5) . ?
C16B H16B 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
C8A O2A H2A 112(3) . . ?
C1A N1A H1A 118(3) . . ?
C1A N1A C9A 120.1(2) . . ?
C9A N1A H1A 121(3) . . ?
O1A C1A N1A 119.9(3) . . ?
O1A C1A C2A 123.5(3) . . ?
N1A C1A C2A 116.6(2) . . ?
C3A C2A C1A 118.9(2) . . ?
C7A C2A C1A 122.3(2) . . ?
C7A C2A C3A 118.8(3) . . ?
C2A C3A H3A 119.8 . . ?
C4A C3A C2A 120.3(2) . . ?
C4A C3A H3A 119.8 . . ?
C3A C4A H4A 119.6 . . ?
C3A C4A C5A 120.8(3) . . ?
C5A C4A H4A 119.6 . . ?
C4A C5A C17A 121.3(3) . . ?
C6A C5A C4A 118.5(3) . . ?
C6A C5A C17A 120.2(3) . . ?
C5A C6A H6A 119.4 . . ?
C7A C6A C5A 121.1(2) . . ?
C7A C6A H6A 119.4 . . ?
C2A C7A H7A 119.8 . . ?
C6A C7A C2A 120.4(3) . . ?
C6A C7A H7A 119.8 . . ?
O2A C8A C9A 110.5(2) . . ?
O3A C8A O2A 125.5(3) . . ?
O3A C8A C9A 124.0(2) . . ?
N1A C9A C8A 110.8(2) . . ?
N1A C9A H9A 109.0 . . ?
N1A C9A C10A 109.6(2) . . ?
C8A C9A H9A 109.0 . . ?
C8A C9A C10A 109.4(2) . . ?
C10A C9A H9A 109.0 . . ?
C9A C10A H10A 109.2 . . ?
C9A C10A H10B 109.2 . . ?
H10A C10A H10B 107.9 . . ?
C11A C10A C9A 112.1(2) . . ?
C11A C10A H10A 109.2 . . ?
C11A C10A H10B 109.2 . . ?
C12A C11A C10A 120.0(3) . . ?
C16A C11A C10A 121.5(2) . . ?
C16A C11A C12A 118.5(3) . . ?
C11A C12A H12A 119.5 . . ?
C13A C12A C11A 121.0(3) . . ?
C13A C12A H12A 119.5 . . ?
C12A C13A H13A 120.0 . . ?
C14A C13A C12A 119.9(3) . . ?
C14A C13A H13A 120.0 . . ?
C13A C14A H14A 120.0 . . ?
C13A C14A C15A 119.9(3) . . ?
C15A C14A H14A 120.0 . . ?
C14A C15A H15A 119.9 . . ?
C14A C15A C16A 120.2(3) . . ?
C16A C15A H15A 119.9 . . ?
C11A C16A H16A 119.8 . . ?
C15A C16A C11A 120.5(3) . . ?
C15A C16A H16A 119.8 . . ?
C5A C17A H17A 109.5 . . ?
C5A C17A H17B 109.5 . . ?
C5A C17A H17C 109.5 . . ?
H17A C17A H17B 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
C8B O2B H2B 111(3) . . ?
C1B N1B H1B 121(2) . . ?
C1B N1B C9B 120.5(2) . . ?
C9B N1B H1B 118(2) . . ?
O1B C1B N1B 120.1(3) . . ?
O1B C1B C2B 122.6(3) . . ?
N1B C1B C2B 117.3(2) . . ?
C3B C2B C1B 119.7(2) . . ?
C3B C2B C7B 119.1(3) . . ?
C7B C2B C1B 121.3(2) . . ?
C2B C3B H3B 119.5 . . ?
C4B C3B C2B 121.0(3) . . ?
C4B C3B H3B 119.5 . . ?
C3B C4B H4B 120.5 . . ?
C5B C4B C3B 119.1(3) . . ?
C5B C4B H4B 120.5 . . ?
C4B C5B Cl1B 119.7(2) . . ?
C6B C5B Cl1B 119.0(2) . . ?
C6B C5B C4B 121.3(3) . . ?
C5B C6B H6B 120.3 . . ?
C5B C6B C7B 119.3(3) . . ?
C7B C6B H6B 120.3 . . ?
C2B C7B H7B 119.8 . . ?
C6B C7B C2B 120.3(3) . . ?
C6B C7B H7B 119.8 . . ?
O2B C8B C9B 111.0(2) . . ?
O3B C8B O2B 125.1(3) . . ?
O3B C8B C9B 123.9(2) . . ?
N1B C9B C8B 111.2(2) . . ?
N1B C9B H9B 108.3 . . ?
N1B C9B C10B 109.9(2) . . ?
C8B C9B H9B 108.3 . . ?
C8B C9B C10B 110.8(2) . . ?
C10B C9B H9B 108.3 . . ?
C9B C10B H10C 109.3 . . ?
C9B C10B H10D 109.3 . . ?
H10C C10B H10D 107.9 . . ?
C11B C10B C9B 111.7(2) . . ?
C11B C10B H10C 109.3 . . ?
C11B C10B H10D 109.3 . . ?
C12B C11B C10B 119.9(3) . . ?
C16B C11B C10B 121.3(3) . . ?
C16B C11B C12B 118.8(3) . . ?
C11B C12B H12B 119.6 . . ?
C11B C12B C13B 120.8(3) . . ?
C13B C12B H12B 119.6 . . ?
C12B C13B H13B 120.4 . . ?
C14B C13B C12B 119.2(3) . . ?
C14B C13B H13B 120.4 . . ?
C13B C14B H14B 119.9 . . ?
C15B C14B C13B 120.1(3) . . ?
C15B C14B H14B 119.9 . . ?
C14B C15B H15B 119.7 . . ?
C14B C15B C16B 120.6(3) . . ?
C16B C15B H15B 119.7 . . ?
C11B C16B C15B 120.5(3) . . ?
C11B C16B H16B 119.8 . . ?
C15B C16B H16B 119.8 . . ?

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
O2A H2A O1A 0.90(5) 1.69(5) 2.591(3) 174(4) 2_647 yes
N1A H1A O3B 0.81(4) 2.21(4) 2.999(3) 165(4) . yes
O2B H2B O1B 0.83(4) 1.78(5) 2.598(3) 168(4) 2_556 yes
N1B H1B O3A 0.89(4) 2.09(4) 2.967(3) 168(3) . 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
O1A C1A C2A C3A -16.9(4) . . . . ?
O1A C1A C2A C7A 162.9(3) . . . . ?
O2A C8A C9A N1A -157.8(2) . . . . ?
O2A C8A C9A C10A 81.3(3) . . . . ?
O3A C8A C9A N1A 23.9(4) . . . . ?
O3A C8A C9A C10A -97.0(3) . . . . ?
N1A C1A C2A C3A 163.6(2) . . . . ?
N1A C1A C2A C7A -16.6(4) . . . . ?
N1A C9A C10A C11A 68.5(3) . . . . ?
C1A N1A C9A C8A 68.6(3) . . . . ?
C1A N1A C9A C10A -170.6(2) . . . . ?
C1A C2A C3A C4A 179.4(3) . . . . ?
C1A C2A C7A C6A 179.6(3) . . . . ?
C2A C3A C4A C5A 0.5(5) . . . . ?
C3A C2A C7A C6A -0.7(4) . . . . ?
C3A C4A C5A C6A 0.5(5) . . . . ?
C3A C4A C5A C17A -178.6(3) . . . . ?
C4A C5A C6A C7A -1.6(5) . . . . ?
C5A C6A C7A C2A 1.7(5) . . . . ?
C7A C2A C3A C4A -0.4(4) . . . . ?
C8A C9A C10A C11A -169.8(2) . . . . ?
C9A N1A C1A O1A 0.0(4) . . . . ?
C9A N1A C1A C2A 179.6(2) . . . . ?
C9A C10A C11A C12A 83.3(3) . . . . ?
C9A C10A C11A C16A -95.8(3) . . . . ?
C10A C11A C12A C13A -179.3(3) . . . . ?
C10A C11A C16A C15A 178.7(3) . . . . ?
C11A C12A C13A C14A 0.6(5) . . . . ?
C12A C11A C16A C15A -0.4(5) . . . . ?
C12A C13A C14A C15A -0.3(5) . . . . ?
C13A C14A C15A C16A -0.4(5) . . . . ?
C14A C15A C16A C11A 0.8(5) . . . . ?
C16A C11A C12A C13A -0.2(5) . . . . ?
C17A C5A C6A C7A 177.5(3) . . . . ?
Cl1B C5B C6B C7B 179.7(2) . . . . ?
O1B C1B C2B C3B 17.1(4) . . . . ?
O1B C1B C2B C7B -163.2(3) . . . . ?
O2B C8B C9B N1B 158.1(2) . . . . ?
O2B C8B C9B C10B -79.4(3) . . . . ?
O3B C8B C9B N1B -22.3(4) . . . . ?
O3B C8B C9B C10B 100.3(3) . . . . ?
N1B C1B C2B C3B -162.2(3) . . . . ?
N1B C1B C2B C7B 17.5(4) . . . . ?
N1B C9B C10B C11B -69.0(3) . . . . ?
C1B N1B C9B C8B -70.1(3) . . . . ?
C1B N1B C9B C10B 166.9(2) . . . . ?
C1B C2B C3B C4B 178.7(3) . . . . ?
C1B C2B C7B C6B -177.9(3) . . . . ?
C2B C3B C4B C5B -0.1(5) . . . . ?
C3B C2B C7B C6B 1.8(4) . . . . ?
C3B C4B C5B Cl1B -178.9(2) . . . . ?
C3B C4B C5B C6B 0.6(5) . . . . ?
C4B C5B C6B C7B 0.2(5) . . . . ?
C5B C6B C7B C2B -1.3(4) . . . . ?
C7B C2B C3B C4B -1.0(4) . . . . ?
C8B C9B C10B C11B 167.7(2) . . . . ?
C9B N1B C1B O1B 0.8(4) . . . . ?
C9B N1B C1B C2B -179.9(2) . . . . ?
C9B C10B C11B C12B -83.1(3) . . . . ?
C9B C10B C11B C16B 94.2(3) . . . . ?
C10B C11B C12B C13B 178.3(3) . . . . ?
C10B C11B C16B C15B -177.7(3) . . . . ?
C11B C12B C13B C14B -0.6(5) . . . . ?
C12B C11B C16B C15B -0.4(5) . . . . ?
C12B C13B C14B C15B -0.4(5) . . . . ?
C13B C14B C15B C16B 0.9(5) . . . . ?
C14B C15B C16B C11B -0.5(5) . . . . ?
C16B C11B C12B C13B 1.0(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
####################################################################### 
# 
# 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_22kaw10_a
_database_code_depnum_ccdc_archive 'CCDC 2312809'
loop_
_audit_author_name
_audit_author_address
'Kraig Wheeler'
;Whitworth University
United States of America
;
_audit_update_record             
;
2023-12-18 deposited with the CCDC.	2024-02-12 downloaded from the CCDC.
;
_audit_creation_date             2023-12-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H17 N O3'
_chemical_formula_sum            'C13 H17 N O3'
_chemical_formula_weight         235.27
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   10.7023(4)
_cell_length_b                   9.0828(3)
_cell_length_c                   13.3370(5)
_cell_angle_alpha                90
_cell_angle_beta                 103.692(2)
_cell_angle_gamma                90
_cell_volume                     1259.61(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9913
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.25
_cell_measurement_theta_min      4.25
_shelx_estimated_absorpt_T_max   0.917
_shelx_estimated_absorpt_T_min   0.771
_exptl_absorpt_coefficient_mu    0.719
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6480
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.381
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.122
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            25092
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.239
_diffrn_reflns_theta_min         4.252
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'κ-geometry four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'focusing mirror'
_diffrn_radiation_detector       'Bruker PHOTON II'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2277
_reflns_number_total             2483
_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       'SAINT+ V8.40B (Bruker AXS Inc., 2020)'
_computing_data_collection       'APEX4 Ver. 8.38A (Bruker-AXS, 2022)'
_computing_data_reduction        'SAINT+ Ve8.40B (Bruker-AXS, 2020)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2019/1)'
_computing_structure_solution    'XT (Sheldrick, 2018/2)'
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2483
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0356
_refine_ls_restrained_S_all      1.045
_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)+(0.0435P)²+0.4834P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.0921
_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron density map and refined using anisotropic displacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv of the connected C atoms (1.5xUeqiv for methyl groups). Those H atoms
 attached to nitrogen and oxygen were located in Fourier diff maps and assigned Uiso = 1.2xUeqiv for nitrogen (1.5 for oxygen).
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_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 0.46432(8) 0.82339(9) 0.34468(6) 0.0272(2) Uani 1 1 d . . . . .
O2 O 0.65726(8) 0.51974(9) 0.28231(6) 0.0259(2) Uani 1 1 d . . . . .
H2 H 0.6158(16) 0.4503(18) 0.2331(13) 0.039 Uiso 1 1 d . U . . .
O3 O 0.48646(8) 0.48183(9) 0.34884(6) 0.0233(2) Uani 1 1 d . . . . .
N1 N 0.56275(9) 0.70451(10) 0.48925(7) 0.0207(2) Uani 1 1 d . . . . .
H1 H 0.5530(13) 0.6617(16) 0.5460(12) 0.025 Uiso 1 1 d . U . . .
C1 C 0.46636(11) 0.78696(12) 0.43477(8) 0.0214(2) Uani 1 1 d . . . . .
C2 C 0.36145(11) 0.82787(12) 0.48609(9) 0.0222(2) Uani 1 1 d . . . . .
C3 C 0.23711(12) 0.84340(13) 0.42450(10) 0.0280(3) Uani 1 1 d . . . . .
H3 H 0.222344 0.835569 0.351601 0.034 Uiso 1 1 calc R U . . .
C4 C 0.13520(12) 0.87022(15) 0.46948(11) 0.0335(3) Uani 1 1 d . . . . .
H4 H 0.050315 0.878286 0.427602 0.040 Uiso 1 1 calc R U . . .
C5 C 0.15719(13) 0.88531(15) 0.57580(11) 0.0335(3) Uani 1 1 d . . . . .
H5 H 0.087248 0.903782 0.606593 0.040 Uiso 1 1 calc R U . . .
C6 C 0.28095(13) 0.87351(14) 0.63720(10) 0.0314(3) Uani 1 1 d . . . . .
H6 H 0.295916 0.886078 0.709787 0.038 Uiso 1 1 calc R U . . .
C7 C 0.38297(12) 0.84335(13) 0.59272(9) 0.0258(3) Uani 1 1 d . . . . .
H7 H 0.467465 0.833257 0.634984 0.031 Uiso 1 1 calc R U . . .
C8 C 0.58914(11) 0.54052(12) 0.35154(8) 0.0205(2) Uani 1 1 d . . . . .
C9 C 0.65701(11) 0.64265(12) 0.43870(8) 0.0205(2) Uani 1 1 d . . . . .
H9 H 0.700193 0.724114 0.409350 0.025 Uiso 1 1 calc R U . . .
C10 C 0.75894(11) 0.55249(12) 0.51503(8) 0.0220(2) Uani 1 1 d . . . . .
H10A H 0.714740 0.493671 0.558765 0.026 Uiso 1 1 calc R U . . .
H10B H 0.798932 0.482525 0.475009 0.026 Uiso 1 1 calc R U . . .
C11 C 0.86636(12) 0.64148(14) 0.58594(9) 0.0279(3) Uani 1 1 d . . . . .
H11 H 0.909675 0.702188 0.541511 0.033 Uiso 1 1 calc R U . . .
C12 C 0.81741(13) 0.74503(16) 0.65797(11) 0.0380(3) Uani 1 1 d . . . . .
H12A H 0.766726 0.689121 0.697212 0.057 Uiso 1 1 calc R U . . .
H12B H 0.763369 0.821312 0.617285 0.057 Uiso 1 1 calc R U . . .
H12C H 0.890638 0.791280 0.705757 0.057 Uiso 1 1 calc R U . . .
C13 C 0.96563(13) 0.53502(17) 0.64807(10) 0.0377(3) Uani 1 1 d . . . . .
H13A H 1.039152 0.590775 0.687954 0.057 Uiso 1 1 calc R U . . .
H13B H 0.994874 0.467731 0.600901 0.057 Uiso 1 1 calc R U . . .
H13C H 0.926551 0.478264 0.695204 0.057 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 1.2415(14) . ?
O2 H2 0.942(17) . ?
O2 C8 1.3185(14) . ?
O3 C8 1.2142(14) . ?
N1 H1 0.879(15) . ?
N1 C1 1.3410(15) . ?
N1 C9 1.4526(14) . ?
C1 C2 1.4937(16) . ?
C2 C3 1.3957(17) . ?
C2 C7 1.3929(17) . ?
C3 H3 0.9500 . ?
C3 C4 1.3851(18) . ?
C4 H4 0.9500 . ?
C4 C5 1.388(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.3868(19) . ?
C6 H6 0.9500 . ?
C6 C7 1.3877(18) . ?
C7 H7 0.9500 . ?
C8 C9 1.5296(15) . ?
C9 H9 1.0000 . ?
C9 C10 1.5398(15) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5344(16) . ?
C11 H11 1.0000 . ?
C11 C12 1.5233(18) . ?
C11 C13 1.5276(18) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O2 H2 109.7(10) . . ?
C1 N1 H1 118.7(9) . . ?
C1 N1 C9 119.62(9) . . ?
C9 N1 H1 117.8(9) . . ?
O1 C1 N1 120.55(11) . . ?
O1 C1 C2 122.30(10) . . ?
N1 C1 C2 117.12(10) . . ?
C3 C2 C1 118.09(10) . . ?
C7 C2 C1 122.17(10) . . ?
C7 C2 C3 119.67(11) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.10(12) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 119.96(12) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.18(12) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 120.07(12) . . ?
C7 C6 H6 120.0 . . ?
C2 C7 H7 120.0 . . ?
C6 C7 C2 119.98(11) . . ?
C6 C7 H7 120.0 . . ?
O2 C8 C9 112.16(9) . . ?
O3 C8 O2 124.26(10) . . ?
O3 C8 C9 123.53(10) . . ?
N1 C9 C8 109.29(9) . . ?
N1 C9 H9 109.4 . . ?
N1 C9 C10 111.10(9) . . ?
C8 C9 H9 109.4 . . ?
C8 C9 C10 108.34(9) . . ?
C10 C9 H9 109.4 . . ?
C9 C10 H10A 108.3 . . ?
C9 C10 H10B 108.3 . . ?
H10A C10 H10B 107.4 . . ?
C11 C10 C9 115.95(10) . . ?
C11 C10 H10A 108.3 . . ?
C11 C10 H10B 108.3 . . ?
C10 C11 H11 108.1 . . ?
C12 C11 C10 113.24(10) . . ?
C12 C11 H11 108.1 . . ?
C12 C11 C13 110.34(11) . . ?
C13 C11 C10 108.93(10) . . ?
C13 C11 H11 108.1 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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
O2 H2 O1 0.942(17) 1.649(18) 2.5882(11) 174.4(16) 2_645 yes
N1 H1 O3 0.879(15) 2.031(15) 2.8884(12) 164.9(13) 3_666 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
O1 C1 C2 C3 30.28(16) . . . . ?
O1 C1 C2 C7 -153.00(11) . . . . ?
O2 C8 C9 N1 158.93(9) . . . . ?
O2 C8 C9 C10 -79.88(11) . . . . ?
O3 C8 C9 N1 -23.42(14) . . . . ?
O3 C8 C9 C10 97.77(12) . . . . ?
N1 C1 C2 C3 -147.84(11) . . . . ?
N1 C1 C2 C7 28.88(15) . . . . ?
N1 C9 C10 C11 -79.98(12) . . . . ?
C1 N1 C9 C8 -60.63(13) . . . . ?
C1 N1 C9 C10 179.88(9) . . . . ?
C1 C2 C3 C4 175.11(11) . . . . ?
C1 C2 C7 C6 -176.43(11) . . . . ?
C2 C3 C4 C5 1.60(19) . . . . ?
C3 C2 C7 C6 0.24(17) . . . . ?
C3 C4 C5 C6 0.0(2) . . . . ?
C4 C5 C6 C7 -1.4(2) . . . . ?
C5 C6 C7 C2 1.30(19) . . . . ?
C7 C2 C3 C4 -1.70(18) . . . . ?
C8 C9 C10 C11 159.96(10) . . . . ?
C9 N1 C1 O1 -7.45(16) . . . . ?
C9 N1 C1 C2 170.71(9) . . . . ?
C9 C10 C11 C12 62.65(14) . . . . ?
C9 C10 C11 C13 -174.18(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
####################################################################### 
# 
# 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_21kaw34_a
_database_code_depnum_ccdc_archive 'CCDC 2312808'
loop_
_audit_author_name
_audit_author_address
'Kraig Wheeler'
;Whitworth University
United States of America
;
_audit_update_record             
;
2024-01-24 deposited with the CCDC.	2024-02-12 downloaded from the CCDC.
;
_audit_creation_date             2024-01-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H17 N O3, C13 H16 Cl N O3'
_chemical_formula_sum            'C30 H33 Cl N2 O6'
_chemical_formula_weight         553.03
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.7094(3)
_cell_length_b                   9.8205(3)
_cell_length_c                   14.5002(4)
_cell_angle_alpha                90
_cell_angle_beta                 111.2860(10)
_cell_angle_gamma                90
_cell_volume                     1420.97(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9919
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.03
_cell_measurement_theta_min      3.27
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.566
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6335
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             584
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 1.00 0.00 0.2450
0.00 -1.00 0.00 0.2070
-1.00 0.00 -1.00 0.0260
1.00 0.00 1.00 0.0260
-1.00 0.00 0.00 0.0320
1.00 0.00 -1.00 0.0230
-1.00 0.00 1.00 0.0360
-1.00 -1.00 0.00 0.1300
0.00 0.00 1.00 0.0310

_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.052
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            31726
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.206
_diffrn_reflns_theta_min         3.271
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'κ-geometry four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'focusing mirror'
_diffrn_radiation_detector       'Bruker PHOTON II'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.877
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                5264
_reflns_number_total             5553
_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       'SAINT+ V8.40B (Bruker AXS Inc., 2020)'
_computing_data_collection       'APEX5 Ver.2022.08-RC130 (Bruker-AXS, 2023)'
_computing_data_reduction        'SAINT+ Ve8.40B (Bruker-AXS, 2020)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2019/1)'
_computing_structure_solution    'XT (Sheldrick, 2018/2)'
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 2342 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.012(5)
_refine_ls_extinction_coef       0.0011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     368
_refine_ls_number_reflns         5553
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0282
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0339P)²+0.2969P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0693
_refine_ls_wR_factor_ref         0.0706
_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier 
electron density map and refined using anisotropic displacement 
parameters. All C-H hydrogen atoms were placed in calculated 
positions with Uiso = 1.2xUeqiv of the connected C atoms 
(1.5xUeqiv for methyl groups). Those H atoms attached to nitrogen 
and oxygen were located in Fourier diff mapsand assigned Uiso = 
1.2xUeqiv for NH groups (Uiso = 1.5xUeqiv for OH groups).
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9A(H9A), C9B(H9B), C11B(H11B)
2.b Secondary CH2 refined with riding coordinates:
 C10A(H10A,H10B), C10B(H10C,H10D)
2.c Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C4A(H4A), C6A(H6A), C7A(H7A), C12A(H12A), C13A(H13A), C14A(H14A),
 C15A(H15A), C16A(H16A), C3B(H3B), C4B(H4B), C6B(H6B), C7B(H7B)
2.d Idealised Me refined as rotating group:
 C17A(H17A,H17B,H17C), C12B(H12B,H12C,H12D), C13B(H13B,H13C,H13D)
;
_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 0.40364(15) 0.22409(16) 0.92280(11) 0.0178(3) Uani 1 1 d . . . . .
O2A O 0.59438(15) 0.54602(18) 0.94257(11) 0.0225(4) Uani 1 1 d . . . . .
H2A H 0.593(3) 0.601(4) 0.986(2) 0.034 Uiso 1 1 d . U . . .
O3A O 0.37081(14) 0.54336(15) 0.89758(10) 0.0179(3) Uani 1 1 d . . . . .
N1A N 0.35308(19) 0.32380(19) 0.77426(14) 0.0157(4) Uani 1 1 d . . . . .
H1A H 0.290(3) 0.345(3) 0.720(2) 0.019 Uiso 1 1 d . U . . .
C1A C 0.3246(2) 0.2380(2) 0.83601(15) 0.0143(4) Uani 1 1 d . . . . .
C2A C 0.1954(2) 0.1621(2) 0.79455(15) 0.0157(4) Uani 1 1 d . . . . .
C3A C 0.1370(2) 0.1109(2) 0.85879(16) 0.0180(4) Uani 1 1 d . . . . .
H3A H 0.178528 0.126642 0.927907 0.022 Uiso 1 1 calc R U . . .
C4A C 0.0185(2) 0.0369(2) 0.82285(16) 0.0208(5) Uani 1 1 d . . . . .
H4A H -0.020610 0.003163 0.867574 0.025 Uiso 1 1 calc R U . . .
C5A C -0.0439(2) 0.0116(2) 0.72143(17) 0.0191(5) Uani 1 1 d . . . . .
C6A C 0.0126(2) 0.0665(3) 0.65769(15) 0.0195(4) Uani 1 1 d . . . . .
H6A H -0.030752 0.053314 0.588421 0.023 Uiso 1 1 calc R U . . .
C7A C 0.1310(2) 0.1402(2) 0.69267(16) 0.0172(4) Uani 1 1 d . . . . .
H7A H 0.168588 0.175797 0.647584 0.021 Uiso 1 1 calc R U . . .
C8A C 0.4725(2) 0.5047(2) 0.88723(15) 0.0155(4) Uani 1 1 d . . . . .
C9A C 0.4753(2) 0.4039(2) 0.80817(15) 0.0157(4) Uani 1 1 d . . . . .
H9A H 0.553408 0.341348 0.837322 0.019 Uiso 1 1 calc R U . . .
C10A C 0.4903(2) 0.4796(2) 0.71938(16) 0.0184(4) Uani 1 1 d . . . . .
H10A H 0.407708 0.532386 0.684951 0.022 Uiso 1 1 calc R U . . .
H10B H 0.565747 0.544760 0.744102 0.022 Uiso 1 1 calc R U . . .
C11A C 0.5155(2) 0.3834(2) 0.64635(15) 0.0178(4) Uani 1 1 d . . . . .
C12A C 0.4114(2) 0.3261(2) 0.56767(16) 0.0211(5) Uani 1 1 d . . . . .
H12A H 0.321283 0.349437 0.557593 0.025 Uiso 1 1 calc R U . . .
C13A C 0.4378(3) 0.2351(3) 0.50380(17) 0.0252(5) Uani 1 1 d . . . . .
H13A H 0.365810 0.196061 0.450774 0.030 Uiso 1 1 calc R U . . .
C14A C 0.5686(3) 0.2009(3) 0.51694(17) 0.0253(5) Uani 1 1 d . . . . .
H14A H 0.586234 0.137832 0.473531 0.030 Uiso 1 1 calc R U . . .
C15A C 0.6738(3) 0.2592(3) 0.59375(19) 0.0256(5) Uani 1 1 d . . . . .
H15A H 0.763827 0.237575 0.602399 0.031 Uiso 1 1 calc R U . . .
C16A C 0.6466(2) 0.3494(3) 0.65794(17) 0.0231(5) Uani 1 1 d . . . . .
H16A H 0.718830 0.388616 0.710723 0.028 Uiso 1 1 calc R U . . .
C17A C -0.1689(2) -0.0748(3) 0.68141(19) 0.0255(5) Uani 1 1 d . . . . .
H17A H -0.247742 -0.015627 0.656144 0.038 Uiso 1 1 calc R U . . .
H17B H -0.176055 -0.132381 0.734478 0.038 Uiso 1 1 calc R U . . .
H17C H -0.163930 -0.132444 0.627678 0.038 Uiso 1 1 calc R U . . .
Cl1B Cl 0.68541(5) 1.07483(6) 0.85044(4) 0.02737(15) Uani 1 1 d . . . . .
O1B O 0.09683(16) 0.77207(17) 0.58789(11) 0.0206(3) Uani 1 1 d . . . . .
O2B O -0.08651(15) 0.45455(18) 0.54431(11) 0.0214(3) Uani 1 1 d . . . . .
H2B H -0.085(3) 0.395(4) 0.501(2) 0.032 Uiso 1 1 d . U . . .
O3B O 0.13809(15) 0.44391(16) 0.59809(10) 0.0193(3) Uani 1 1 d . . . . .
N1B N 0.15130(19) 0.65642(19) 0.73026(13) 0.0161(4) Uani 1 1 d . . . . .
H1B H 0.212(3) 0.626(3) 0.781(2) 0.019 Uiso 1 1 d . U . . .
C1B C 0.1771(2) 0.7526(2) 0.67421(16) 0.0168(4) Uani 1 1 d . . . . .
C2B C 0.3033(2) 0.8328(2) 0.71959(16) 0.0164(4) Uani 1 1 d . . . . .
C3B C 0.3566(2) 0.9011(2) 0.65814(16) 0.0201(5) Uani 1 1 d . . . . .
H3B H 0.312207 0.895979 0.588383 0.024 Uiso 1 1 calc R U . . .
C4B C 0.4737(2) 0.9764(3) 0.69736(17) 0.0213(5) Uani 1 1 d . . . . .
H4B H 0.509094 1.023708 0.655152 0.026 Uiso 1 1 calc R U . . .
C5B C 0.5380(2) 0.9814(2) 0.79925(17) 0.0198(5) Uani 1 1 d . . . . .
C6B C 0.4875(2) 0.9146(2) 0.86234(16) 0.0198(5) Uani 1 1 d . . . . .
H6B H 0.533218 0.918796 0.932004 0.024 Uiso 1 1 calc R U . . .
C7B C 0.3690(2) 0.8414(2) 0.82214(16) 0.0184(4) Uani 1 1 d . . . . .
H7B H 0.332385 0.796733 0.864698 0.022 Uiso 1 1 calc R U . . .
C8B C 0.0350(2) 0.4847(2) 0.60561(15) 0.0156(4) Uani 1 1 d . . . . .
C9B C 0.0314(2) 0.5729(2) 0.69131(14) 0.0161(4) Uani 1 1 d . . . . .
H9B H -0.048718 0.633925 0.666851 0.019 Uiso 1 1 calc R U . . .
C10B C 0.0178(2) 0.4789(2) 0.77223(15) 0.0171(4) Uani 1 1 d . . . . .
H10C H -0.034405 0.397566 0.739821 0.021 Uiso 1 1 calc R U . . .
H10D H 0.108428 0.447383 0.814402 0.021 Uiso 1 1 calc R U . . .
C11B C -0.0491(2) 0.5424(2) 0.83911(16) 0.0217(5) Uani 1 1 d . . . . .
H11B H -0.140337 0.574637 0.796248 0.026 Uiso 1 1 calc R U . . .
C12B C 0.0281(3) 0.6633(3) 0.89838(19) 0.0307(6) Uani 1 1 d . . . . .
H12B H -0.016393 0.696372 0.942377 0.046 Uiso 1 1 calc R U . . .
H12C H 0.030666 0.736254 0.853002 0.046 Uiso 1 1 calc R U . . .
H12D H 0.119756 0.635063 0.937921 0.046 Uiso 1 1 calc R U . . .
C13B C -0.0658(3) 0.4324(3) 0.90888(17) 0.0289(5) Uani 1 1 d . . . . .
H13B H 0.022324 0.407602 0.957125 0.043 Uiso 1 1 calc R U . . .
H13C H -0.108282 0.351871 0.870362 0.043 Uiso 1 1 calc R U . . .
H13D H -0.122156 0.467600 0.943753 0.043 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
O1A C1A 1.243(3) . ?
O2A H2A 0.84(3) . ?
O2A C8A 1.324(3) . ?
O3A C8A 1.213(3) . ?
N1A H1A 0.86(3) . ?
N1A C1A 1.343(3) . ?
N1A C9A 1.451(3) . ?
C1A C2A 1.493(3) . ?
C2A C3A 1.391(3) . ?
C2A C7A 1.402(3) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.389(3) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.399(3) . ?
C5A C6A 1.384(3) . ?
C5A C17A 1.512(3) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.387(3) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.523(3) . ?
C9A H9A 1.0000 . ?
C9A C10A 1.545(3) . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C10A C11A 1.514(3) . ?
C11A C12A 1.392(3) . ?
C11A C16A 1.393(3) . ?
C12A H12A 0.9500 . ?
C12A C13A 1.388(3) . ?
C13A H13A 0.9500 . ?
C13A C14A 1.384(3) . ?
C14A H14A 0.9500 . ?
C14A C15A 1.388(4) . ?
C15A H15A 0.9500 . ?
C15A C16A 1.390(3) . ?
C16A H16A 0.9500 . ?
C17A H17A 0.9800 . ?
C17A H17B 0.9800 . ?
C17A H17C 0.9800 . ?
Cl1B C5B 1.742(2) . ?
O1B C1B 1.250(3) . ?
O2B H2B 0.86(3) . ?
O2B C8B 1.316(3) . ?
O3B C8B 1.216(3) . ?
N1B H1B 0.84(3) . ?
N1B C1B 1.339(3) . ?
N1B C9B 1.454(3) . ?
C1B C2B 1.494(3) . ?
C2B C3B 1.392(3) . ?
C2B C7B 1.398(3) . ?
C3B H3B 0.9500 . ?
C3B C4B 1.388(3) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.386(3) . ?
C5B C6B 1.385(3) . ?
C6B H6B 0.9500 . ?
C6B C7B 1.390(3) . ?
C7B H7B 0.9500 . ?
C8B C9B 1.527(3) . ?
C9B H9B 1.0000 . ?
C9B C10B 1.541(3) . ?
C10B H10C 0.9900 . ?
C10B H10D 0.9900 . ?
C10B C11B 1.532(3) . ?
C11B H11B 1.0000 . ?
C11B C12B 1.522(3) . ?
C11B C13B 1.534(3) . ?
C12B H12B 0.9800 . ?
C12B H12C 0.9800 . ?
C12B H12D 0.9800 . ?
C13B H13B 0.9800 . ?
C13B H13C 0.9800 . ?
C13B H13D 0.9800 . ?

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
C8A O2A H2A 112(2) . . ?
C1A N1A H1A 118.2(19) . . ?
C1A N1A C9A 120.63(18) . . ?
C9A N1A H1A 119.5(19) . . ?
O1A C1A N1A 120.5(2) . . ?
O1A C1A C2A 122.95(19) . . ?
N1A C1A C2A 116.54(18) . . ?
C3A C2A C1A 119.16(18) . . ?
C3A C2A C7A 118.8(2) . . ?
C7A C2A C1A 122.02(19) . . ?
C2A C3A H3A 119.7 . . ?
C4A C3A C2A 120.6(2) . . ?
C4A C3A H3A 119.7 . . ?
C3A C4A H4A 119.7 . . ?
C3A C4A C5A 120.6(2) . . ?
C5A C4A H4A 119.7 . . ?
C4A C5A C17A 121.4(2) . . ?
C6A C5A C4A 118.4(2) . . ?
C6A C5A C17A 120.2(2) . . ?
C5A C6A H6A 119.3 . . ?
C5A C6A C7A 121.49(19) . . ?
C7A C6A H6A 119.3 . . ?
C2A C7A H7A 120.0 . . ?
C6A C7A C2A 120.0(2) . . ?
C6A C7A H7A 120.0 . . ?
O2A C8A C9A 111.78(18) . . ?
O3A C8A O2A 124.1(2) . . ?
O3A C8A C9A 124.09(19) . . ?
N1A C9A C8A 110.23(17) . . ?
N1A C9A H9A 108.9 . . ?
N1A C9A C10A 109.43(17) . . ?
C8A C9A H9A 108.9 . . ?
C8A C9A C10A 110.57(17) . . ?
C10A C9A H9A 108.9 . . ?
C9A C10A H10A 109.1 . . ?
C9A C10A H10B 109.1 . . ?
H10A C10A H10B 107.8 . . ?
C11A C10A C9A 112.44(18) . . ?
C11A C10A H10A 109.1 . . ?
C11A C10A H10B 109.1 . . ?
C12A C11A C10A 122.2(2) . . ?
C12A C11A C16A 118.3(2) . . ?
C16A C11A C10A 119.5(2) . . ?
C11A C12A H12A 119.7 . . ?
C13A C12A C11A 120.7(2) . . ?
C13A C12A H12A 119.7 . . ?
C12A C13A H13A 119.8 . . ?
C14A C13A C12A 120.4(2) . . ?
C14A C13A H13A 119.8 . . ?
C13A C14A H14A 120.1 . . ?
C13A C14A C15A 119.8(2) . . ?
C15A C14A H14A 120.1 . . ?
C14A C15A H15A 120.2 . . ?
C14A C15A C16A 119.6(2) . . ?
C16A C15A H15A 120.2 . . ?
C11A C16A H16A 119.4 . . ?
C15A C16A C11A 121.3(2) . . ?
C15A C16A H16A 119.4 . . ?
C5A C17A H17A 109.5 . . ?
C5A C17A H17B 109.5 . . ?
C5A C17A H17C 109.5 . . ?
H17A C17A H17B 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
C8B O2B H2B 112(2) . . ?
C1B N1B H1B 121.5(19) . . ?
C1B N1B C9B 120.67(18) . . ?
C9B N1B H1B 115.4(19) . . ?
O1B C1B N1B 119.8(2) . . ?
O1B C1B C2B 122.9(2) . . ?
N1B C1B C2B 117.24(19) . . ?
C3B C2B C1B 119.16(19) . . ?
C3B C2B C7B 119.1(2) . . ?
C7B C2B C1B 121.72(19) . . ?
C2B C3B H3B 119.5 . . ?
C4B C3B C2B 120.9(2) . . ?
C4B C3B H3B 119.5 . . ?
C3B C4B H4B 120.6 . . ?
C5B C4B C3B 118.8(2) . . ?
C5B C4B H4B 120.6 . . ?
C4B C5B Cl1B 119.73(18) . . ?
C6B C5B Cl1B 118.60(17) . . ?
C6B C5B C4B 121.7(2) . . ?
C5B C6B H6B 120.5 . . ?
C5B C6B C7B 119.0(2) . . ?
C7B C6B H6B 120.5 . . ?
C2B C7B H7B 119.7 . . ?
C6B C7B C2B 120.5(2) . . ?
C6B C7B H7B 119.7 . . ?
O2B C8B C9B 111.51(18) . . ?
O3B C8B O2B 124.9(2) . . ?
O3B C8B C9B 123.50(18) . . ?
N1B C9B C8B 110.88(17) . . ?
N1B C9B H9B 108.8 . . ?
N1B C9B C10B 110.88(16) . . ?
C8B C9B H9B 108.8 . . ?
C8B C9B C10B 108.48(19) . . ?
C10B C9B H9B 108.8 . . ?
C9B C10B H10C 108.4 . . ?
C9B C10B H10D 108.4 . . ?
H10C C10B H10D 107.4 . . ?
C11B C10B C9B 115.65(18) . . ?
C11B C10B H10C 108.4 . . ?
C11B C10B H10D 108.4 . . ?
C10B C11B H11B 108.2 . . ?
C10B C11B C13B 108.92(19) . . ?
C12B C11B C10B 113.06(19) . . ?
C12B C11B H11B 108.2 . . ?
C12B C11B C13B 110.25(19) . . ?
C13B C11B H11B 108.2 . . ?
C11B C12B H12B 109.5 . . ?
C11B C12B H12C 109.5 . . ?
C11B C12B H12D 109.5 . . ?
H12B C12B H12C 109.5 . . ?
H12B C12B H12D 109.5 . . ?
H12C C12B H12D 109.5 . . ?
C11B C13B H13B 109.5 . . ?
C11B C13B H13C 109.5 . . ?
C11B C13B H13D 109.5 . . ?
H13B C13B H13C 109.5 . . ?
H13B C13B H13D 109.5 . . ?
H13C C13B H13D 109.5 . . ?

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
O2A H2A O1A 0.84(3) 1.78(4) 2.615(2) 176(3) 2_657 yes
N1A H1A O3B 0.86(3) 2.15(3) 2.991(2) 166(3) . yes
O2B H2B O1B 0.86(3) 1.74(4) 2.597(2) 175(3) 2_546 yes
N1B H1B O3A 0.84(3) 2.08(3) 2.916(2) 174(3) . 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
O1A C1A C2A C3A 22.7(3) . . . . ?
O1A C1A C2A C7A -157.1(2) . . . . ?
O2A C8A C9A N1A 158.89(17) . . . . ?
O2A C8A C9A C10A -80.0(2) . . . . ?
O3A C8A C9A N1A -21.8(3) . . . . ?
O3A C8A C9A C10A 99.3(2) . . . . ?
N1A C1A C2A C3A -157.5(2) . . . . ?
N1A C1A C2A C7A 22.7(3) . . . . ?
N1A C9A C10A C11A -67.4(2) . . . . ?
C1A N1A C9A C8A -65.0(2) . . . . ?
C1A N1A C9A C10A 173.24(19) . . . . ?
C1A C2A C3A C4A -178.4(2) . . . . ?
C1A C2A C7A C6A 178.6(2) . . . . ?
C2A C3A C4A C5A 0.5(3) . . . . ?
C3A C2A C7A C6A -1.1(3) . . . . ?
C3A C4A C5A C6A -2.4(3) . . . . ?
C3A C4A C5A C17A 176.8(2) . . . . ?
C4A C5A C6A C7A 2.6(3) . . . . ?
C5A C6A C7A C2A -0.9(4) . . . . ?
C7A C2A C3A C4A 1.3(3) . . . . ?
C8A C9A C10A C11A 170.97(18) . . . . ?
C9A N1A C1A O1A -1.3(3) . . . . ?
C9A N1A C1A C2A 178.93(18) . . . . ?
C9A C10A C11A C12A 89.3(2) . . . . ?
C9A C10A C11A C16A -90.1(2) . . . . ?
C10A C11A C12A C13A -178.1(2) . . . . ?
C10A C11A C16A C15A 178.6(2) . . . . ?
C11A C12A C13A C14A -0.6(4) . . . . ?
C12A C11A C16A C15A -0.8(3) . . . . ?
C12A C13A C14A C15A -0.7(4) . . . . ?
C13A C14A C15A C16A 1.2(4) . . . . ?
C14A C15A C16A C11A -0.4(4) . . . . ?
C16A C11A C12A C13A 1.4(3) . . . . ?
C17A C5A C6A C7A -176.6(2) . . . . ?
Cl1B C5B C6B C7B 179.14(17) . . . . ?
O1B C1B C2B C3B -20.5(3) . . . . ?
O1B C1B C2B C7B 159.4(2) . . . . ?
O2B C8B C9B N1B -153.25(18) . . . . ?
O2B C8B C9B C10B 84.8(2) . . . . ?
O3B C8B C9B N1B 29.4(3) . . . . ?
O3B C8B C9B C10B -92.6(2) . . . . ?
N1B C1B C2B C3B 159.7(2) . . . . ?
N1B C1B C2B C7B -20.4(3) . . . . ?
N1B C9B C10B C11B 84.6(2) . . . . ?
C1B N1B C9B C8B 64.4(3) . . . . ?
C1B N1B C9B C10B -175.07(19) . . . . ?
C1B C2B C3B C4B -179.8(2) . . . . ?
C1B C2B C7B C6B 178.8(2) . . . . ?
C2B C3B C4B C5B 0.8(4) . . . . ?
C3B C2B C7B C6B -1.3(3) . . . . ?
C3B C4B C5B Cl1B 179.82(18) . . . . ?
C3B C4B C5B C6B -0.7(4) . . . . ?
C4B C5B C6B C7B -0.3(3) . . . . ?
C5B C6B C7B C2B 1.3(3) . . . . ?
C7B C2B C3B C4B 0.2(3) . . . . ?
C8B C9B C10B C11B -153.43(19) . . . . ?
C9B N1B C1B O1B 0.8(3) . . . . ?
C9B N1B C1B C2B -179.38(18) . . . . ?
C9B C10B C11B C12B -62.0(3) . . . . ?
C9B C10B C11B C13B 175.07(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
####################################################################### 
# 
# 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_23kaw59
_database_code_depnum_ccdc_archive 'CCDC 2312814'
loop_
_audit_author_name
_audit_author_address
'Kraig Wheeler'
;Whitworth University
United States of America
;
_audit_update_record             
;
2023-12-18 deposited with the CCDC.	2024-02-12 downloaded from the CCDC.
;
_audit_creation_date             2023-12-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H16 F3 N O3, C17 H14 F3 N O3'
_chemical_formula_sum            'C31 H30 F6 N2 O6'
_chemical_formula_weight         640.57
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.8243(8)
_cell_length_b                   9.1832(5)
_cell_length_c                   13.8585(8)
_cell_angle_alpha                90
_cell_angle_beta                 117.871(3)
_cell_angle_gamma                90
_cell_volume                     1555.27(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9899
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.74
_cell_measurement_theta_min      3.61
_shelx_estimated_absorpt_T_max   0.971
_shelx_estimated_absorpt_T_min   0.821
_exptl_absorpt_coefficient_mu    1.024
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.201
_exptl_crystal_size_mid          0.131
_exptl_crystal_size_min          0.029
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20421
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.859
_diffrn_reflns_theta_min         3.608
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'κ-geometry four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'focusing mirror'
_diffrn_radiation_detector       'Bruker PHOTON II'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.847
_reflns_Friedel_fraction_full    0.978
_reflns_Friedel_fraction_max     0.959
_reflns_number_gt                5418
_reflns_number_total             6082
_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       'SAINT+ V8.40B (Bruker AXS Inc., 2020)'
_computing_data_collection       'APEX5 Ver.2022.08-RC130 (Bruker-AXS, 2023)'
_computing_data_reduction        'SAINT+ Ve8.40B (Bruker-AXS, 2020)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2019/1)'
_computing_structure_solution    'XT (Sheldrick, 2018/2)'
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 
;
 Flack x determined using 2235 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     475
_refine_ls_number_reflns         6082
_refine_ls_number_restraints     121
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0511
_refine_ls_restrained_S_all      1.126
_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)+(0.0579P)²+0.9984P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1242
_refine_ls_wR_factor_ref         0.1321
_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron density map and refined using anisotropic displacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv of the connected C atoms (1.5xUeqiv for methyl groups). Those H atoms
 attached to nitrogen and oxygen were located in Fourier diff maps and assigned Uiso = 1.2xUeqiv for nitrogen (1.5xUeqiv for oxygen).
The two CF3 groups exhibit two-part disorder with occupancies refined to a 1:1 ratio.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 F2A-C14 \\sim F2-C14 \\sim F3-C14 \\sim F3A-C14 \\sim F1-C14 \\sim F1A-C14
 with sigma of 0.02
 F2A-C5 \\sim F2-C5 \\sim F3-C5 \\sim F3A-C5 \\sim F1-C5 \\sim F1A-C5
 with sigma of 0.02
 F2B-C17A \\sim F2C-C17A \\sim F1C-C17A \\sim F1B-C17A \\sim F3C-C17A \\sim
F3B-C17A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F1C) \\sim Ueq, Uanis(F1B) \\sim Ueq, Uanis(F3C) \\sim Ueq, Uanis(F3B)
\\sim Ueq, Uanis(F2C) \\sim Ueq, Uanis(F2B) \\sim Ueq, Uanis(F3) \\sim Ueq,
Uanis(F3A) \\sim Ueq, Uanis(F1A) \\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(F2A)
\\sim Ueq, Uanis(F2) \\sim Ueq: with sigma of 0.001 and sigma for terminal
atoms of 0.002
4. Same fragment restrains
{F1C, F2C, F3C} sigma for 1-2: 0.02, 1-3: 0.04
as in
{F1B, F2B, F3B}
{F1A, F2A, F3A} sigma for 1-2: 0.02, 1-3: 0.04
as in
{F1A, F2A, F3A}
5. Others
 Fixed Sof: F1(0.5) F2(0.5) F3(0.5) F1A(0.5) F2A(0.5) F3A(0.5) F1C(0.5)
 F2C(0.5) F3C(0.5) F1B(0.5) F2B(0.5) F3B(0.5)
6.a Ternary CH refined with riding coordinates:
 C9(H9), C11(H11), C9A(H9A)
6.b Secondary CH2 refined with riding coordinates:
 C10(H10C,H10D), C10A(H10A,H10B)
6.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C3A(H3A), C4A(H4A), C6A(H6A), C7A(H7A),
 C12A(H12A), C13A(H13A), C14A(H14A), C15A(H15A), C16A(H16A)
6.d Idealised Me refined as rotating group:
 C12(H12B,H12C,H12D), C13(H13B,H13C,H13D)
;
_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 -0.3853(2) 0.3141(3) 0.0328(2) 0.0320(6) Uani 1 1 d . . . . .
O2 O -0.5555(2) 0.0085(3) -0.1296(2) 0.0340(7) Uani 1 1 d . . . . .
H2 H -0.569(4) -0.060(6) -0.092(4) 0.051 Uiso 1 1 d . U . . .
O3 O -0.3888(2) -0.0312(3) 0.0104(2) 0.0300(6) Uani 1 1 d . . . . .
N1 N -0.3055(3) 0.1991(3) -0.0541(3) 0.0268(7) Uani 1 1 d . . . . .
H1 H -0.248(4) 0.160(5) -0.044(4) 0.032 Uiso 1 1 d . U . . .
C1 C -0.3011(3) 0.2832(4) 0.0265(3) 0.0268(8) Uani 1 1 d . . . . .
C2 C -0.1904(3) 0.3340(4) 0.1083(3) 0.0272(8) Uani 1 1 d . . . . .
C3 C -0.1703(3) 0.3564(5) 0.2151(4) 0.0355(9) Uani 1 1 d . . . . .
H3 H -0.227254 0.344001 0.234458 0.043 Uiso 1 1 calc R U . . .
C4 C -0.0670(4) 0.3967(5) 0.2930(4) 0.0394(10) Uani 1 1 d . . . . .
H4 H -0.052466 0.411060 0.366455 0.047 Uiso 1 1 calc R U . . .
C5 C 0.0158(3) 0.4162(5) 0.2644(4) 0.0359(9) Uani 1 1 d D . . . .
C6 C -0.0038(3) 0.3959(4) 0.1578(4) 0.0338(9) Uani 1 1 d . . . . .
H6 H 0.053116 0.410334 0.138691 0.041 Uiso 1 1 calc R U . . .
C7 C -0.1068(3) 0.3546(4) 0.0796(3) 0.0304(8) Uani 1 1 d . . . . .
H7 H -0.120916 0.340038 0.006319 0.036 Uiso 1 1 calc R U . . .
C8 C -0.4478(3) 0.0293(4) -0.0738(3) 0.0263(8) Uani 1 1 d . . . . .
C9 C -0.4091(3) 0.1369(4) -0.1322(3) 0.0265(7) Uani 1 1 d . . . . .
H9 H -0.464182 0.216926 -0.163567 0.032 Uiso 1 1 calc R U . . .
C10 C -0.3978(3) 0.0617(4) -0.2256(3) 0.0317(8) Uani 1 1 d . . . . .
H10C H -0.329913 0.002862 -0.193390 0.038 Uiso 1 1 calc R U . . .
H10D H -0.459950 -0.006393 -0.262489 0.038 Uiso 1 1 calc R U . . .
C11 C -0.3945(4) 0.1628(5) -0.3121(4) 0.0391(9) Uani 1 1 d . . . . .
H11 H -0.378306 0.099381 -0.361489 0.047 Uiso 1 1 calc R U . . .
C12 C -0.3064(5) 0.2768(6) -0.2689(5) 0.0538(12) Uani 1 1 d . . . . .
H12B H -0.323836 0.349444 -0.227512 0.081 Uiso 1 1 calc R U . . .
H12C H -0.301936 0.324435 -0.329937 0.081 Uiso 1 1 calc R U . . .
H12D H -0.236087 0.230945 -0.220966 0.081 Uiso 1 1 calc R U . . .
C13 C -0.5064(5) 0.2311(7) -0.3833(4) 0.0630(15) Uani 1 1 d . . . . .
H13B H -0.560750 0.153965 -0.418358 0.095 Uiso 1 1 calc R U . . .
H13C H -0.502633 0.292163 -0.439447 0.095 Uiso 1 1 calc R U . . .
H13D H -0.527745 0.290992 -0.337827 0.095 Uiso 1 1 calc R U . . .
C14 C 0.1278(4) 0.4620(6) 0.3485(4) 0.0462(11) Uani 1 1 d D . . . .
F1 F 0.2029(6) 0.3543(9) 0.3587(6) 0.055(2) Uani 0.5 1 d D U P A 1
F2 F 0.1355(8) 0.4799(9) 0.4474(7) 0.042(2) Uani 0.5 1 d D U P A 1
F3 F 0.1618(9) 0.5807(12) 0.3266(10) 0.076(4) Uani 0.5 1 d D U P A 1
F1A F 0.2069(5) 0.4021(8) 0.3348(6) 0.0449(16) Uani 0.5 1 d D U P A 2
F2A F 0.1472(7) 0.4384(9) 0.4503(6) 0.040(2) Uani 0.5 1 d D U P A 2
F3A F 0.1438(5) 0.6098(7) 0.3342(6) 0.0355(15) Uani 0.5 1 d D U P A 2
O1A O 0.8918(2) 0.6899(3) 0.9720(2) 0.0326(6) Uani 1 1 d . . . . .
O2A O 1.0588(2) 0.9992(3) 1.1378(3) 0.0345(7) Uani 1 1 d . . . . .
H2A H 1.073(4) 1.056(6) 1.109(4) 0.038(14) Uiso 1 1 d . . . . .
O3A O 0.8913(2) 1.0300(3) 0.9974(2) 0.0285(6) Uani 1 1 d . . . . .
N1A N 0.8134(3) 0.7969(4) 1.0637(3) 0.0281(7) Uani 1 1 d . . . . .
H1A H 0.753(4) 0.846(6) 1.057(4) 0.034 Uiso 1 1 d . U . . .
C1A C 0.8079(3) 0.7209(4) 0.9792(3) 0.0278(8) Uani 1 1 d . . . . .
C2A C 0.6960(3) 0.6821(4) 0.8928(3) 0.0278(8) Uani 1 1 d . . . . .
C3A C 0.6772(3) 0.6797(4) 0.7843(3) 0.0320(8) Uani 1 1 d . . . . .
H3A H 0.736766 0.689158 0.768493 0.038 Uiso 1 1 calc R U . . .
C4A C 0.5717(3) 0.6635(5) 0.7002(3) 0.0348(9) Uani 1 1 d . . . . .
H4A H 0.557988 0.665510 0.626377 0.042 Uiso 1 1 calc R U . . .
C5A C 0.4860(3) 0.6442(4) 0.7252(4) 0.0360(9) Uani 1 1 d . . . . .
C6A C 0.5043(3) 0.6395(5) 0.8327(4) 0.0359(9) Uani 1 1 d . . . . .
H6A H 0.445262 0.623709 0.848452 0.043 Uiso 1 1 calc R U . . .
C7A C 0.6101(3) 0.6582(4) 0.9169(4) 0.0320(8) Uani 1 1 d . . . . .
H7A H 0.623754 0.654679 0.990676 0.038 Uiso 1 1 calc R U . . .
C8A C 0.9535(3) 0.9724(4) 1.0834(3) 0.0269(8) Uani 1 1 d . . . . .
C9A C 0.9167(3) 0.8604(4) 1.1416(3) 0.0288(8) Uani 1 1 d . . . . .
H9A H 0.973068 0.781722 1.172469 0.035 Uiso 1 1 calc R U . . .
C10A C 0.9047(3) 0.9346(5) 1.2355(3) 0.0336(9) Uani 1 1 d . . . . .
H10A H 0.971067 0.993145 1.279574 0.040 Uiso 1 1 calc R U . . .
H10B H 0.841493 1.002010 1.204040 0.040 Uiso 1 1 calc R U . . .
C11A C 0.8883(4) 0.8275(5) 1.3095(4) 0.0366(9) Uani 1 1 d . . . . .
C12A C 0.7840(3) 0.7759(5) 1.2839(4) 0.0407(10) Uani 1 1 d . . . . .
H12A H 0.722480 0.808753 1.219401 0.049 Uiso 1 1 calc R U . . .
C13A C 0.7694(4) 0.6770(6) 1.3518(4) 0.0485(11) Uani 1 1 d . . . . .
H13A H 0.697974 0.642688 1.333252 0.058 Uiso 1 1 calc R U . . .
C14A C 0.8570(4) 0.6285(5) 1.4452(4) 0.0503(11) Uani 1 1 d . . . . .
H14A H 0.846201 0.562216 1.491911 0.060 Uiso 1 1 calc R U . . .
C15A C 0.9611(4) 0.6763(5) 1.4714(4) 0.0493(11) Uani 1 1 d . . . . .
H15A H 1.022133 0.642542 1.535879 0.059 Uiso 1 1 calc R U . . .
C16A C 0.9763(4) 0.7749(5) 1.4023(4) 0.0416(10) Uani 1 1 d . . . . .
H16A H 1.048175 0.805896 1.419589 0.050 Uiso 1 1 calc R U . . .
C17A C 0.3709(4) 0.6400(5) 0.6343(4) 0.0470(11) Uani 1 1 d D . . . .
F1C F 0.3646(6) 0.5420(8) 0.5544(6) 0.0464(17) Uani 0.5 1 d D U P B 1
F2C F 0.2952(5) 0.6129(8) 0.6593(6) 0.0438(15) Uani 0.5 1 d D U P B 1
F3C F 0.3436(6) 0.7708(9) 0.5783(7) 0.068(2) Uani 0.5 1 d D U P B 1
F1B F 0.3610(6) 0.5982(9) 0.5414(6) 0.0495(18) Uani 0.5 1 d D U P B 2
F2B F 0.3085(6) 0.5493(9) 0.6635(6) 0.0576(19) Uani 0.5 1 d D U P B 2
F3B F 0.3238(6) 0.7707(8) 0.6189(6) 0.0619(17) Uani 0.5 1 d D U P B 2


_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 1.240(4) . ?
O2 H2 0.89(6) . ?
O2 C8 1.332(4) . ?
O3 C8 1.202(5) . ?
N1 H1 0.82(5) . ?
N1 C1 1.336(5) . ?
N1 C9 1.449(5) . ?
C1 C2 1.491(5) . ?
C2 C3 1.387(6) . ?
C2 C7 1.401(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.378(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.386(6) . ?
C5 C6 1.384(6) . ?
C5 C14 1.498(6) . ?
C6 H6 0.9500 . ?
C6 C7 1.379(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.525(5) . ?
C9 H9 1.0000 . ?
C9 C10 1.537(5) . ?
C10 H10C 0.9900 . ?
C10 H10D 0.9900 . ?
C10 C11 1.535(6) . ?
C11 H11 1.0000 . ?
C11 C12 1.502(7) . ?
C11 C13 1.528(7) . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C12 H12D 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C13 H13D 0.9800 . ?
C14 F1 1.393(9) . ?
C14 F2 1.334(10) . ?
C14 F3 1.279(11) . ?
C14 F1A 1.315(8) . ?
C14 F2A 1.325(9) . ?
C14 F3A 1.404(8) . ?
O1A C1A 1.244(5) . ?
O2A H2A 0.74(6) . ?
O2A C8A 1.313(5) . ?
O3A C8A 1.217(5) . ?
N1A H1A 0.92(5) . ?
N1A C1A 1.334(5) . ?
N1A C9A 1.451(5) . ?
C1A C2A 1.490(5) . ?
C2A C3A 1.401(6) . ?
C2A C7A 1.393(5) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.385(6) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.393(6) . ?
C5A C6A 1.390(6) . ?
C5A C17A 1.499(6) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.391(6) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.533(5) . ?
C9A H9A 1.0000 . ?
C9A C10A 1.546(6) . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C10A C11A 1.513(6) . ?
C11A C12A 1.397(6) . ?
C11A C16A 1.379(6) . ?
C12A H12A 0.9500 . ?
C12A C13A 1.389(7) . ?
C13A H13A 0.9500 . ?
C13A C14A 1.370(7) . ?
C14A H14A 0.9500 . ?
C14A C15A 1.381(7) . ?
C15A H15A 0.9500 . ?
C15A C16A 1.404(7) . ?
C16A H16A 0.9500 . ?
C17A F1C 1.397(8) . ?
C17A F2C 1.272(8) . ?
C17A F3C 1.383(9) . ?
C17A F1B 1.288(9) . ?
C17A F2B 1.388(8) . ?
C17A F3B 1.335(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O2 H2 104(4) . . ?
C1 N1 H1 116(3) . . ?
C1 N1 C9 119.7(3) . . ?
C9 N1 H1 120(3) . . ?
O1 C1 N1 121.0(4) . . ?
O1 C1 C2 122.5(4) . . ?
N1 C1 C2 116.5(3) . . ?
C3 C2 C1 118.7(3) . . ?
C3 C2 C7 120.2(4) . . ?
C7 C2 C1 121.1(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.5(4) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.1(4) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C14 120.3(4) . . ?
C6 C5 C4 120.8(4) . . ?
C6 C5 C14 118.9(4) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 C5 119.4(4) . . ?
C7 C6 H6 120.3 . . ?
C2 C7 H7 120.0 . . ?
C6 C7 C2 120.0(4) . . ?
C6 C7 H7 120.0 . . ?
O2 C8 C9 111.0(3) . . ?
O3 C8 O2 124.3(4) . . ?
O3 C8 C9 124.6(3) . . ?
N1 C9 C8 109.1(3) . . ?
N1 C9 H9 108.7 . . ?
N1 C9 C10 110.6(3) . . ?
C8 C9 H9 108.7 . . ?
C8 C9 C10 110.8(3) . . ?
C10 C9 H9 108.7 . . ?
C9 C10 H10C 108.3 . . ?
C9 C10 H10D 108.3 . . ?
H10C C10 H10D 107.4 . . ?
C11 C10 C9 116.0(3) . . ?
C11 C10 H10C 108.3 . . ?
C11 C10 H10D 108.3 . . ?
C10 C11 H11 106.3 . . ?
C12 C11 C10 115.1(4) . . ?
C12 C11 H11 106.3 . . ?
C12 C11 C13 111.0(5) . . ?
C13 C11 C10 111.2(4) . . ?
C13 C11 H11 106.3 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
C11 C12 H12D 109.5 . . ?
H12B C12 H12C 109.5 . . ?
H12B C12 H12D 109.5 . . ?
H12C C12 H12D 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
C11 C13 H13D 109.5 . . ?
H13B C13 H13C 109.5 . . ?
H13B C13 H13D 109.5 . . ?
H13C C13 H13D 109.5 . . ?
F1 C14 C5 109.3(5) . . ?
F2 C14 C5 113.0(5) . . ?
F2 C14 F1 106.6(6) . . ?
F3 C14 C5 114.6(6) . . ?
F3 C14 F1 106.8(7) . . ?
F3 C14 F2 106.1(7) . . ?
F1A C14 C5 113.4(5) . . ?
F1A C14 F2A 108.5(6) . . ?
F1A C14 F3A 100.8(6) . . ?
F2A C14 C5 113.8(5) . . ?
F2A C14 F3A 110.0(6) . . ?
F3A C14 C5 109.6(5) . . ?
C8A O2A H2A 109(4) . . ?
C1A N1A H1A 120(3) . . ?
C1A N1A C9A 119.7(3) . . ?
C9A N1A H1A 114(3) . . ?
O1A C1A N1A 121.2(4) . . ?
O1A C1A C2A 122.5(4) . . ?
N1A C1A C2A 116.3(3) . . ?
C3A C2A C1A 117.9(3) . . ?
C7A C2A C1A 121.7(4) . . ?
C7A C2A C3A 120.2(4) . . ?
C2A C3A H3A 120.0 . . ?
C4A C3A C2A 119.9(4) . . ?
C4A C3A H3A 120.0 . . ?
C3A C4A H4A 120.4 . . ?
C3A C4A C5A 119.2(4) . . ?
C5A C4A H4A 120.4 . . ?
C4A C5A C17A 119.1(4) . . ?
C6A C5A C4A 121.3(4) . . ?
C6A C5A C17A 119.4(4) . . ?
C5A C6A H6A 120.4 . . ?
C5A C6A C7A 119.3(4) . . ?
C7A C6A H6A 120.4 . . ?
C2A C7A H7A 120.1 . . ?
C6A C7A C2A 119.9(4) . . ?
C6A C7A H7A 120.1 . . ?
O2A C8A C9A 112.0(3) . . ?
O3A C8A O2A 124.5(4) . . ?
O3A C8A C9A 123.4(3) . . ?
N1A C9A C8A 109.4(3) . . ?
N1A C9A H9A 109.1 . . ?
N1A C9A C10A 110.3(3) . . ?
C8A C9A H9A 109.1 . . ?
C8A C9A C10A 109.9(3) . . ?
C10A C9A H9A 109.1 . . ?
C9A C10A H10A 108.9 . . ?
C9A C10A H10B 108.9 . . ?
H10A C10A H10B 107.8 . . ?
C11A C10A C9A 113.2(3) . . ?
C11A C10A H10A 108.9 . . ?
C11A C10A H10B 108.9 . . ?
C12A C11A C10A 120.8(4) . . ?
C16A C11A C10A 120.8(4) . . ?
C16A C11A C12A 118.3(4) . . ?
C11A C12A H12A 119.7 . . ?
C13A C12A C11A 120.6(4) . . ?
C13A C12A H12A 119.7 . . ?
C12A C13A H13A 119.7 . . ?
C14A C13A C12A 120.6(4) . . ?
C14A C13A H13A 119.7 . . ?
C13A C14A H14A 120.1 . . ?
C13A C14A C15A 119.8(4) . . ?
C15A C14A H14A 120.1 . . ?
C14A C15A H15A 120.1 . . ?
C14A C15A C16A 119.8(4) . . ?
C16A C15A H15A 120.1 . . ?
C11A C16A C15A 120.9(4) . . ?
C11A C16A H16A 119.6 . . ?
C15A C16A H16A 119.6 . . ?
F1C C17A C5A 109.3(5) . . ?
F2C C17A C5A 117.5(5) . . ?
F2C C17A F1C 109.6(5) . . ?
F2C C17A F3C 106.2(6) . . ?
F3C C17A C5A 110.7(5) . . ?
F3C C17A F1C 102.5(6) . . ?
F1B C17A C5A 115.0(5) . . ?
F1B C17A F2B 108.8(6) . . ?
F1B C17A F3B 107.0(6) . . ?
F2B C17A C5A 109.3(5) . . ?
F3B C17A C5A 111.0(4) . . ?
F3B C17A F2B 105.2(6) . . ?

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
O2 H2 O1 0.89(6) 1.70(6) 2.585(4) 172(5) 2_445 yes
N1 H1 O3A 0.82(5) 2.11(5) 2.917(4) 170(5) 1_444 yes
O2A H2A O1A 0.74(6) 1.87(6) 2.611(4) 176(6) 2_757 yes
N1A H1A O3 0.92(5) 2.08(5) 2.987(4) 168(4) 1_666 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
O1 C1 C2 C3 30.0(6) . . . . ?
O1 C1 C2 C7 -152.1(4) . . . . ?
O2 C8 C9 N1 158.2(3) . . . . ?
O2 C8 C9 C10 -79.7(4) . . . . ?
O3 C8 C9 N1 -23.3(5) . . . . ?
O3 C8 C9 C10 98.8(4) . . . . ?
N1 C1 C2 C3 -148.8(4) . . . . ?
N1 C1 C2 C7 29.1(5) . . . . ?
N1 C9 C10 C11 -77.1(4) . . . . ?
C1 N1 C9 C8 -65.3(4) . . . . ?
C1 N1 C9 C10 172.5(3) . . . . ?
C1 C2 C3 C4 176.9(4) . . . . ?
C1 C2 C7 C6 -177.3(4) . . . . ?
C2 C3 C4 C5 0.7(7) . . . . ?
C3 C2 C7 C6 0.5(6) . . . . ?
C3 C4 C5 C6 0.1(7) . . . . ?
C3 C4 C5 C14 179.1(4) . . . . ?
C4 C5 C6 C7 -0.6(6) . . . . ?
C4 C5 C14 F1 118.5(6) . . . . ?
C4 C5 C14 F2 0.0(7) . . . . ?
C4 C5 C14 F3 -121.7(7) . . . . ?
C4 C5 C14 F1A 143.9(5) . . . . ?
C4 C5 C14 F2A 19.2(7) . . . . ?
C4 C5 C14 F3A -104.4(6) . . . . ?
C5 C6 C7 C2 0.2(6) . . . . ?
C6 C5 C14 F1 -62.5(6) . . . . ?
C6 C5 C14 F2 179.0(5) . . . . ?
C6 C5 C14 F3 57.4(8) . . . . ?
C6 C5 C14 F1A -37.1(7) . . . . ?
C6 C5 C14 F2A -161.7(6) . . . . ?
C6 C5 C14 F3A 74.7(6) . . . . ?
C7 C2 C3 C4 -1.0(6) . . . . ?
C8 C9 C10 C11 161.8(3) . . . . ?
C9 N1 C1 O1 -3.2(6) . . . . ?
C9 N1 C1 C2 175.6(3) . . . . ?
C9 C10 C11 C12 56.2(5) . . . . ?
C9 C10 C11 C13 -71.2(5) . . . . ?
C14 C5 C6 C7 -179.6(4) . . . . ?
O1A C1A C2A C3A -32.3(6) . . . . ?
O1A C1A C2A C7A 151.9(4) . . . . ?
O2A C8A C9A N1A -159.8(3) . . . . ?
O2A C8A C9A C10A 79.0(4) . . . . ?
O3A C8A C9A N1A 20.9(5) . . . . ?
O3A C8A C9A C10A -100.4(4) . . . . ?
N1A C1A C2A C3A 145.0(4) . . . . ?
N1A C1A C2A C7A -30.8(5) . . . . ?
N1A C9A C10A C11A 69.5(4) . . . . ?
C1A N1A C9A C8A 62.5(4) . . . . ?
C1A N1A C9A C10A -176.5(3) . . . . ?
C1A C2A C3A C4A -171.4(4) . . . . ?
C1A C2A C7A C6A 172.3(4) . . . . ?
C2A C3A C4A C5A -2.4(6) . . . . ?
C3A C2A C7A C6A -3.4(6) . . . . ?
C3A C4A C5A C6A -0.6(6) . . . . ?
C3A C4A C5A C17A 174.6(4) . . . . ?
C4A C5A C6A C7A 1.7(6) . . . . ?
C4A C5A C17A F1C 49.9(6) . . . . ?
C4A C5A C17A F2C 175.6(5) . . . . ?
C4A C5A C17A F3C -62.2(6) . . . . ?
C4A C5A C17A F1B 26.0(7) . . . . ?
C4A C5A C17A F2B 148.7(5) . . . . ?
C4A C5A C17A F3B -95.6(6) . . . . ?
C5A C6A C7A C2A 0.4(6) . . . . ?
C6A C5A C17A F1C -134.8(5) . . . . ?
C6A C5A C17A F2C -9.1(7) . . . . ?
C6A C5A C17A F3C 113.1(6) . . . . ?
C6A C5A C17A F1B -158.7(6) . . . . ?
C6A C5A C17A F2B -36.0(7) . . . . ?
C6A C5A C17A F3B 79.7(6) . . . . ?
C7A C2A C3A C4A 4.5(6) . . . . ?
C8A C9A C10A C11A -169.8(3) . . . . ?
C9A N1A C1A O1A 7.9(6) . . . . ?
C9A N1A C1A C2A -169.4(3) . . . . ?
C9A C10A C11A C12A -85.6(5) . . . . ?
C9A C10A C11A C16A 92.4(5) . . . . ?
C10A C11A C12A C13A 179.7(4) . . . . ?
C10A C11A C16A C15A 179.6(4) . . . . ?
C11A C12A C13A C14A 0.1(7) . . . . ?
C12A C11A C16A C15A -2.4(7) . . . . ?
C12A C13A C14A C15A -1.1(8) . . . . ?
C13A C14A C15A C16A 0.4(8) . . . . ?
C14A C15A C16A C11A 1.4(7) . . . . ?
C16A C11A C12A C13A 1.6(7) . . . . ?
C17A C5A C6A C7A -173.5(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
####################################################################### 
# 
# 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_22kaw16a
_database_code_depnum_ccdc_archive 'CCDC 2312812'
loop_
_audit_author_name
_audit_author_address
'Kraig Wheeler'
;Whitworth University
United States of America
;
_audit_update_record             
;
2023-12-18 deposited with the CCDC.	2024-02-12 downloaded from the CCDC.
;
_audit_creation_date             2023-12-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H15 N O3, C17 H14 F3 N O3'
_chemical_formula_sum            'C33 H29 F3 N2 O6'
_chemical_formula_weight         606.58
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   12.9498(11)
_cell_length_b                   9.6063(8)
_cell_length_c                   13.1925(11)
_cell_angle_alpha                90
_cell_angle_beta                 117.118(3)
_cell_angle_gamma                90
_cell_volume                     1460.7(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9887
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.32
_cell_measurement_theta_min      3.76
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.910
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6393
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 1.00 0.00 0.0670
-1.00 -1.00 1.00 0.1680
-1.00 0.00 -1.00 0.1860
-1.00 0.00 1.00 0.0260
0.00 1.00 1.00 0.1070
0.00 -1.00 -1.00 0.1710
0.00 0.00 1.00 0.0820
0.00 0.00 -1.00 0.1530
0.00 1.00 -1.00 0.0850
0.00 -1.00 1.00 0.2060
1.00 -1.00 0.00 0.2200
1.00 1.00 -1.00 0.1000
1.00 0.00 -1.00 0.0290

_exptl_crystal_size_max          0.441
_exptl_crystal_size_mid          0.326
_exptl_crystal_size_min          0.058
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            24713
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.317
_diffrn_reflns_theta_min         3.764
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'κ-geometry four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'focusing mirror'
_diffrn_radiation_detector       'Bruker PHOTON II'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.844
_reflns_Friedel_fraction_full    0.958
_reflns_Friedel_fraction_max     0.955
_reflns_number_gt                5093
_reflns_number_total             5234
_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       'SAINT+ V8.40B (Bruker AXS Inc., 2020)'
_computing_data_collection       'APEX4 Ver. 8.38A (Bruker-AXS, 2022)'
_computing_data_reduction        'SAINT+ Ve8.40B (Bruker-AXS, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2018/2)'
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 2276 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.15(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     409
_refine_ls_number_reflns         5234
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0261
_refine_ls_restrained_S_all      1.092
_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)+(0.0340P)²+0.2732P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0660
_refine_ls_wR_factor_ref         0.0671
_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron density map and refined using anisotropic displacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv of the connected C atoms (1.5xUeqiv for methyl groups). Those H atoms
 attached to nitrogen and oxygen were located in Fourier diff maps and assigned Uiso = 1.2xUeqiv for nitrogen (1.5xUeqiv for oxygenedit
).
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9A(H9A), C9B(H9B)
2.b Secondary CH2 refined with riding coordinates:
 C10A(H10C,H10D), C10B(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C4A(H4A), C5A(H5A), C6A(H6A), C7A(H7A), C12A(H12A), C13A(H13A),
 C14A(H14A), C15A(H15A), C16A(H16A), C3B(H3B), C4B(H4B), C6B(H6B), C7B(H7B),
 C12B(H12B), C13B(H13B), C14B(H14B), C15B(H15B), C16B(H16B)
;
_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 0.38416(12) 0.91141(16) 0.90181(12) 0.0207(3) Uani 1 1 d . . . . .
O2A O 0.56232(12) 0.59734(16) 0.94153(12) 0.0223(3) Uani 1 1 d . . . . .
H2A H 0.581(2) 0.542(3) 1.000(2) 0.033 Uiso 1 1 d . U . . .
O3A O 0.37793(11) 0.55947(15) 0.90629(11) 0.0183(3) Uani 1 1 d . . . . .
N1A N 0.30637(15) 0.77519(18) 0.74774(14) 0.0154(3) Uani 1 1 d . . . . .
H1A H 0.247(2) 0.733(3) 0.702(2) 0.018 Uiso 1 1 d . U . . .
C1A C 0.29637(16) 0.8734(2) 0.81432(16) 0.0155(4) Uani 1 1 d . . . . .
C2A C 0.17876(16) 0.9338(2) 0.78133(16) 0.0167(4) Uani 1 1 d . . . . .
C3A C 0.16186(18) 1.0095(2) 0.86249(17) 0.0206(4) Uani 1 1 d . . . . .
H3A H 0.225074 1.024645 0.935647 0.025 Uiso 1 1 calc R U . . .
C4A C 0.05300(18) 1.0632(2) 0.83718(18) 0.0236(4) Uani 1 1 d . . . . .
H4A H 0.041829 1.113800 0.893275 0.028 Uiso 1 1 calc R U . . .
C5A C -0.03916(17) 1.0428(2) 0.73010(18) 0.0222(4) Uani 1 1 d . . . . .
H5A H -0.113464 1.079576 0.712801 0.027 Uiso 1 1 calc R U . . .
C6A C -0.02295(18) 0.9687(2) 0.64805(17) 0.0221(4) Uani 1 1 d . . . . .
H6A H -0.086088 0.955092 0.574575 0.027 Uiso 1 1 calc R U . . .
C7A C 0.08557(17) 0.9143(2) 0.67341(17) 0.0185(4) Uani 1 1 d . . . . .
H7A H 0.096450 0.863746 0.617139 0.022 Uiso 1 1 calc R U . . .
C8A C 0.44921(16) 0.6150(2) 0.88396(16) 0.0164(4) Uani 1 1 d . . . . .
C9A C 0.41701(16) 0.7077(2) 0.77995(16) 0.0166(4) Uani 1 1 d . . . . .
H9A H 0.478167 0.780581 0.798748 0.020 Uiso 1 1 calc R U . . .
C10A C 0.41267(17) 0.6173(2) 0.68182(16) 0.0188(4) Uani 1 1 d . . . . .
H10C H 0.483349 0.558937 0.710358 0.023 Uiso 1 1 calc R U . . .
H10D H 0.344806 0.554418 0.655389 0.023 Uiso 1 1 calc R U . . .
C11A C 0.40439(17) 0.7031(2) 0.58251(16) 0.0186(4) Uani 1 1 d . . . . .
C12A C 0.50484(17) 0.7401(2) 0.57457(17) 0.0206(4) Uani 1 1 d . . . . .
H12A H 0.578172 0.707518 0.630113 0.025 Uiso 1 1 calc R U . . .
C13A C 0.4984(2) 0.8242(2) 0.48619(19) 0.0237(4) Uani 1 1 d . . . . .
H13A H 0.567106 0.848234 0.481149 0.028 Uiso 1 1 calc R U . . .
C14A C 0.3919(2) 0.8730(2) 0.40548(18) 0.0251(5) Uani 1 1 d . . . . .
H14A H 0.387532 0.930972 0.345317 0.030 Uiso 1 1 calc R U . . .
C15A C 0.29146(19) 0.8371(3) 0.41248(18) 0.0265(5) Uani 1 1 d . . . . .
H15A H 0.218441 0.871040 0.357313 0.032 Uiso 1 1 calc R U . . .
C16A C 0.29765(18) 0.7515(2) 0.50024(17) 0.0226(4) Uani 1 1 d . . . . .
H16A H 0.228593 0.726071 0.504004 0.027 Uiso 1 1 calc R U . . .
F1B F 0.74894(11) 0.14003(16) 0.87046(14) 0.0427(4) Uani 1 1 d . . . . .
F2B F 0.67981(11) 0.01994(16) 0.71628(11) 0.0352(3) Uani 1 1 d . . . . .
F3B F 0.67975(11) -0.06257(15) 0.86750(12) 0.0367(3) Uani 1 1 d . . . . .
O1B O 0.12066(12) 0.24018(16) 0.58910(12) 0.0203(3) Uani 1 1 d . . . . .
O2B O -0.06607(12) 0.54931(17) 0.57572(12) 0.0222(3) Uani 1 1 d . . . . .
H2B H -0.081(2) 0.616(3) 0.521(2) 0.033 Uiso 1 1 d . U . . .
O3B O 0.11746(11) 0.59344(15) 0.61255(11) 0.0197(3) Uani 1 1 d . . . . .
N1B N 0.19334(14) 0.36351(18) 0.75149(14) 0.0170(3) Uani 1 1 d . . . . .
H1B H 0.254(2) 0.399(3) 0.806(2) 0.020 Uiso 1 1 d . U . . .
C1B C 0.20492(16) 0.2744(2) 0.67921(16) 0.0153(4) Uani 1 1 d . . . . .
C2B C 0.32518(16) 0.2190(2) 0.71456(16) 0.0155(4) Uani 1 1 d . . . . .
C3B C 0.34281(17) 0.1308(2) 0.64017(17) 0.0202(4) Uani 1 1 d . . . . .
H3B H 0.279417 0.106709 0.569246 0.024 Uiso 1 1 calc R U . . .
C4B C 0.45249(18) 0.0776(2) 0.66897(18) 0.0214(4) Uani 1 1 d . . . . .
H4B H 0.463999 0.016305 0.618517 0.026 Uiso 1 1 calc R U . . .
C5B C 0.54503(17) 0.1147(2) 0.77184(17) 0.0187(4) Uani 1 1 d . . . . .
C6B C 0.52904(17) 0.2016(2) 0.84708(17) 0.0189(4) Uani 1 1 d . . . . .
H6B H 0.592943 0.225975 0.917538 0.023 Uiso 1 1 calc R U . . .
C7B C 0.41901(17) 0.2531(2) 0.81908(16) 0.0185(4) Uani 1 1 d . . . . .
H7B H 0.407479 0.311619 0.871082 0.022 Uiso 1 1 calc R U . . .
C8B C 0.04749(16) 0.5311(2) 0.63296(16) 0.0160(4) Uani 1 1 d . . . . .
C9B C 0.08241(16) 0.4244(2) 0.72878(16) 0.0163(4) Uani 1 1 d . . . . .
H9B H 0.022183 0.349677 0.705867 0.020 Uiso 1 1 calc R U . . .
C10B C 0.09871(17) 0.4918(2) 0.84195(16) 0.0207(4) Uani 1 1 d . . . . .
H10A H 0.137080 0.423112 0.903934 0.025 Uiso 1 1 calc R U . . .
H10B H 0.151943 0.572042 0.858594 0.025 Uiso 1 1 calc R U . . .
C11B C -0.01020(16) 0.5413(2) 0.84463(15) 0.0181(4) Uani 1 1 d . . . . .
C12B C -0.08212(18) 0.4480(2) 0.86312(17) 0.0224(4) Uani 1 1 d . . . . .
H12B H -0.062972 0.351828 0.872807 0.027 Uiso 1 1 calc R U . . .
C13B C -0.18152(18) 0.4941(2) 0.86755(18) 0.0243(5) Uani 1 1 d . . . . .
H13B H -0.230514 0.429224 0.879066 0.029 Uiso 1 1 calc R U . . .
C14B C -0.20961(18) 0.6338(3) 0.85533(18) 0.0265(5) Uani 1 1 d . . . . .
H14B H -0.277561 0.665258 0.858606 0.032 Uiso 1 1 calc R U . . .
C15B C -0.1380(2) 0.7273(3) 0.8383(2) 0.0358(6) Uani 1 1 d . . . . .
H15B H -0.156683 0.823615 0.830171 0.043 Uiso 1 1 calc R U . . .
C16B C -0.0388(2) 0.6816(3) 0.8329(2) 0.0302(5) Uani 1 1 d . . . . .
H16B H 0.009770 0.746881 0.821128 0.036 Uiso 1 1 calc R U . . .
C17B C 0.66277(17) 0.0544(2) 0.80588(18) 0.0232(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A C1A 1.250(2) . ?
O2A H2A 0.87(3) . ?
O2A C8A 1.318(2) . ?
O3A C8A 1.213(2) . ?
N1A H1A 0.84(3) . ?
N1A C1A 1.335(3) . ?
N1A C9A 1.449(3) . ?
C1A C2A 1.497(3) . ?
C2A C3A 1.392(3) . ?
C2A C7A 1.397(3) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.391(3) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.386(3) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.389(3) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.389(3) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.526(3) . ?
C9A H9A 1.0000 . ?
C9A C10A 1.538(3) . ?
C10A H10C 0.9900 . ?
C10A H10D 0.9900 . ?
C10A C11A 1.509(3) . ?
C11A C12A 1.398(3) . ?
C11A C16A 1.392(3) . ?
C12A H12A 0.9500 . ?
C12A C13A 1.389(3) . ?
C13A H13A 0.9500 . ?
C13A C14A 1.385(3) . ?
C14A H14A 0.9500 . ?
C14A C15A 1.389(3) . ?
C15A H15A 0.9500 . ?
C15A C16A 1.392(3) . ?
C16A H16A 0.9500 . ?
F1B C17B 1.334(3) . ?
F2B C17B 1.339(2) . ?
F3B C17B 1.345(3) . ?
O1B C1B 1.237(2) . ?
O2B H2B 0.92(3) . ?
O2B C8B 1.323(2) . ?
O3B C8B 1.215(2) . ?
N1B H1B 0.86(3) . ?
N1B C1B 1.340(3) . ?
N1B C9B 1.450(2) . ?
C1B C2B 1.505(3) . ?
C2B C3B 1.392(3) . ?
C2B C7B 1.399(3) . ?
C3B H3B 0.9500 . ?
C3B C4B 1.389(3) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.386(3) . ?
C5B C6B 1.383(3) . ?
C5B C17B 1.496(3) . ?
C6B H6B 0.9500 . ?
C6B C7B 1.390(3) . ?
C7B H7B 0.9500 . ?
C8B C9B 1.527(3) . ?
C9B H9B 1.0000 . ?
C9B C10B 1.551(3) . ?
C10B H10A 0.9900 . ?
C10B H10B 0.9900 . ?
C10B C11B 1.504(3) . ?
C11B C12B 1.392(3) . ?
C11B C16B 1.388(3) . ?
C12B H12B 0.9500 . ?
C12B C13B 1.388(3) . ?
C13B H13B 0.9500 . ?
C13B C14B 1.380(3) . ?
C14B H14B 0.9500 . ?
C14B C15B 1.382(3) . ?
C15B H15B 0.9500 . ?
C15B C16B 1.389(3) . ?
C16B H16B 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
C8A O2A H2A 112.2(18) . . ?
C1A N1A H1A 119.5(17) . . ?
C1A N1A C9A 120.20(17) . . ?
C9A N1A H1A 116.8(18) . . ?
O1A C1A N1A 119.58(18) . . ?
O1A C1A C2A 122.16(18) . . ?
N1A C1A C2A 118.26(17) . . ?
C3A C2A C1A 118.33(17) . . ?
C3A C2A C7A 119.22(18) . . ?
C7A C2A C1A 122.43(18) . . ?
C2A C3A H3A 119.8 . . ?
C4A C3A C2A 120.43(18) . . ?
C4A C3A H3A 119.8 . . ?
C3A C4A H4A 120.0 . . ?
C5A C4A C3A 119.98(19) . . ?
C5A C4A H4A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
C4A C5A C6A 120.05(19) . . ?
C6A C5A H5A 120.0 . . ?
C5A C6A H6A 120.0 . . ?
C5A C6A C7A 120.02(19) . . ?
C7A C6A H6A 120.0 . . ?
C2A C7A H7A 119.9 . . ?
C6A C7A C2A 120.28(19) . . ?
C6A C7A H7A 119.9 . . ?
O2A C8A C9A 111.69(16) . . ?
O3A C8A O2A 124.92(18) . . ?
O3A C8A C9A 123.29(17) . . ?
N1A C9A C8A 110.69(15) . . ?
N1A C9A H9A 109.0 . . ?
N1A C9A C10A 110.72(16) . . ?
C8A C9A H9A 109.0 . . ?
C8A C9A C10A 108.53(16) . . ?
C10A C9A H9A 109.0 . . ?
C9A C10A H10C 109.1 . . ?
C9A C10A H10D 109.1 . . ?
H10C C10A H10D 107.8 . . ?
C11A C10A C9A 112.57(16) . . ?
C11A C10A H10C 109.1 . . ?
C11A C10A H10D 109.1 . . ?
C12A C11A C10A 120.24(18) . . ?
C16A C11A C10A 120.79(18) . . ?
C16A C11A C12A 118.91(18) . . ?
C11A C12A H12A 119.7 . . ?
C13A C12A C11A 120.62(19) . . ?
C13A C12A H12A 119.7 . . ?
C12A C13A H13A 120.0 . . ?
C14A C13A C12A 120.0(2) . . ?
C14A C13A H13A 120.0 . . ?
C13A C14A H14A 120.0 . . ?
C13A C14A C15A 120.0(2) . . ?
C15A C14A H14A 120.0 . . ?
C14A C15A H15A 120.0 . . ?
C14A C15A C16A 120.1(2) . . ?
C16A C15A H15A 120.0 . . ?
C11A C16A C15A 120.4(2) . . ?
C11A C16A H16A 119.8 . . ?
C15A C16A H16A 119.8 . . ?
C8B O2B H2B 108.5(17) . . ?
C1B N1B H1B 119.5(17) . . ?
C1B N1B C9B 122.16(17) . . ?
C9B N1B H1B 117.1(17) . . ?
O1B C1B N1B 121.21(18) . . ?
O1B C1B C2B 122.61(18) . . ?
N1B C1B C2B 116.18(16) . . ?
C3B C2B C1B 118.43(17) . . ?
C3B C2B C7B 119.30(18) . . ?
C7B C2B C1B 122.27(17) . . ?
C2B C3B H3B 119.8 . . ?
C4B C3B C2B 120.44(19) . . ?
C4B C3B H3B 119.8 . . ?
C3B C4B H4B 120.2 . . ?
C5B C4B C3B 119.54(19) . . ?
C5B C4B H4B 120.2 . . ?
C4B C5B C17B 120.17(19) . . ?
C6B C5B C4B 120.81(19) . . ?
C6B C5B C17B 118.93(18) . . ?
C5B C6B H6B 120.2 . . ?
C5B C6B C7B 119.66(19) . . ?
C7B C6B H6B 120.2 . . ?
C2B C7B H7B 119.9 . . ?
C6B C7B C2B 120.21(19) . . ?
C6B C7B H7B 119.9 . . ?
O2B C8B C9B 113.21(16) . . ?
O3B C8B O2B 123.75(19) . . ?
O3B C8B C9B 123.04(17) . . ?
N1B C9B C8B 109.48(16) . . ?
N1B C9B H9B 109.6 . . ?
N1B C9B C10B 106.38(15) . . ?
C8B C9B H9B 109.6 . . ?
C8B C9B C10B 112.08(17) . . ?
C10B C9B H9B 109.6 . . ?
C9B C10B H10A 108.3 . . ?
C9B C10B H10B 108.3 . . ?
H10A C10B H10B 107.4 . . ?
C11B C10B C9B 115.91(16) . . ?
C11B C10B H10A 108.3 . . ?
C11B C10B H10B 108.3 . . ?
C12B C11B C10B 120.68(19) . . ?
C16B C11B C10B 120.67(19) . . ?
C16B C11B C12B 118.61(19) . . ?
C11B C12B H12B 119.7 . . ?
C13B C12B C11B 120.6(2) . . ?
C13B C12B H12B 119.7 . . ?
C12B C13B H13B 119.8 . . ?
C14B C13B C12B 120.4(2) . . ?
C14B C13B H13B 119.8 . . ?
C13B C14B H14B 120.3 . . ?
C13B C14B C15B 119.4(2) . . ?
C15B C14B H14B 120.3 . . ?
C14B C15B H15B 119.7 . . ?
C14B C15B C16B 120.5(2) . . ?
C16B C15B H15B 119.7 . . ?
C11B C16B C15B 120.5(2) . . ?
C11B C16B H16B 119.8 . . ?
C15B C16B H16B 119.8 . . ?
F1B C17B F2B 106.85(17) . . ?
F1B C17B F3B 105.68(17) . . ?
F1B C17B C5B 113.25(18) . . ?
F2B C17B F3B 106.21(18) . . ?
F2B C17B C5B 112.73(17) . . ?
F3B C17B C5B 111.60(17) . . ?

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
O2A H2A O1A 0.87(3) 1.72(3) 2.576(2) 170(3) 2_647 yes
N1A H1A O3B 0.84(3) 2.05(3) 2.870(2) 168(2) . yes
O2B H2B O1B 0.92(3) 1.77(3) 2.681(2) 175(3) 2_556 yes
N1B H1B O3A 0.86(3) 2.18(3) 2.996(2) 159(2) . 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
O1A C1A C2A C3A -15.0(3) . . . . ?
O1A C1A C2A C7A 166.37(19) . . . . ?
O2A C8A C9A N1A -154.84(17) . . . . ?
O2A C8A C9A C10A 83.5(2) . . . . ?
O3A C8A C9A N1A 28.7(3) . . . . ?
O3A C8A C9A C10A -93.0(2) . . . . ?
N1A C1A C2A C3A 164.54(18) . . . . ?
N1A C1A C2A C7A -14.1(3) . . . . ?
N1A C9A C10A C11A 69.4(2) . . . . ?
C1A N1A C9A C8A 69.1(2) . . . . ?
C1A N1A C9A C10A -170.47(17) . . . . ?
C1A C2A C3A C4A -177.59(19) . . . . ?
C1A C2A C7A C6A 177.90(19) . . . . ?
C2A C3A C4A C5A -0.8(3) . . . . ?
C3A C2A C7A C6A -0.8(3) . . . . ?
C3A C4A C5A C6A 0.1(3) . . . . ?
C4A C5A C6A C7A 0.3(3) . . . . ?
C5A C6A C7A C2A 0.1(3) . . . . ?
C7A C2A C3A C4A 1.1(3) . . . . ?
C8A C9A C10A C11A -168.93(16) . . . . ?
C9A N1A C1A O1A 3.3(3) . . . . ?
C9A N1A C1A C2A -176.18(17) . . . . ?
C9A C10A C11A C12A 93.4(2) . . . . ?
C9A C10A C11A C16A -83.7(2) . . . . ?
C10A C11A C12A C13A -177.09(19) . . . . ?
C10A C11A C16A C15A 176.32(19) . . . . ?
C11A C12A C13A C14A 0.5(3) . . . . ?
C12A C11A C16A C15A -0.9(3) . . . . ?
C12A C13A C14A C15A -0.4(3) . . . . ?
C13A C14A C15A C16A -0.3(3) . . . . ?
C14A C15A C16A C11A 1.0(3) . . . . ?
C16A C11A C12A C13A 0.1(3) . . . . ?
O1B C1B C2B C3B 3.0(3) . . . . ?
O1B C1B C2B C7B -176.91(19) . . . . ?
O2B C8B C9B N1B 153.94(17) . . . . ?
O2B C8B C9B C10B -88.3(2) . . . . ?
O3B C8B C9B N1B -26.7(3) . . . . ?
O3B C8B C9B C10B 91.1(2) . . . . ?
N1B C1B C2B C3B -177.27(18) . . . . ?
N1B C1B C2B C7B 2.8(3) . . . . ?
N1B C9B C10B C11B -170.30(18) . . . . ?
C1B N1B C9B C8B -71.7(2) . . . . ?
C1B N1B C9B C10B 167.02(18) . . . . ?
C1B C2B C3B C4B 179.69(19) . . . . ?
C1B C2B C7B C6B -178.71(19) . . . . ?
C2B C3B C4B C5B -0.9(3) . . . . ?
C3B C2B C7B C6B 1.4(3) . . . . ?
C3B C4B C5B C6B 1.3(3) . . . . ?
C3B C4B C5B C17B 177.86(19) . . . . ?
C4B C5B C6B C7B -0.3(3) . . . . ?
C4B C5B C17B F1B 149.3(2) . . . . ?
C4B C5B C17B F2B 27.8(3) . . . . ?
C4B C5B C17B F3B -91.6(2) . . . . ?
C5B C6B C7B C2B -1.0(3) . . . . ?
C6B C5B C17B F1B -34.1(3) . . . . ?
C6B C5B C17B F2B -155.54(19) . . . . ?
C6B C5B C17B F3B 85.0(2) . . . . ?
C7B C2B C3B C4B -0.4(3) . . . . ?
C8B C9B C10B C11B 70.1(2) . . . . ?
C9B N1B C1B O1B 0.1(3) . . . . ?
C9B N1B C1B C2B -179.60(17) . . . . ?
C9B C10B C11B C12B 80.2(2) . . . . ?
C9B C10B C11B C16B -102.2(2) . . . . ?
C10B C11B C12B C13B 178.87(18) . . . . ?
C10B C11B C16B C15B -178.4(2) . . . . ?
C11B C12B C13B C14B -1.0(3) . . . . ?
C12B C11B C16B C15B -0.7(3) . . . . ?
C12B C13B C14B C15B 0.2(3) . . . . ?
C13B C14B C15B C16B 0.3(4) . . . . ?
C14B C15B C16B C11B 0.0(4) . . . . ?
C16B C11B C12B C13B 1.2(3) . . . . ?
C17B C5B C6B C7B -176.93(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
####################################################################### 
# 
# 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_23kaw42
_database_code_depnum_ccdc_archive 'CCDC 2312813'
loop_
_audit_author_name
_audit_author_address
'Kraig Wheeler'
;Whitworth University
United States of America
;
_audit_update_record             
;
2023-12-18 deposited with the CCDC.	2024-02-12 downloaded from the CCDC.
;
_audit_creation_date             2023-12-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H15 N O3, C13 H17 N O3'
_chemical_formula_sum            'C29 H32 N2 O6'
_chemical_formula_weight         504.56
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.9173(7)
_cell_length_b                   9.1344(6)
_cell_length_c                   14.1599(10)
_cell_angle_alpha                90
_cell_angle_beta                 108.014(2)
_cell_angle_gamma                90
_cell_volume                     1342.85(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9907
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.02
_cell_measurement_theta_min      5.85
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.827
_exptl_absorpt_coefficient_mu    0.715
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6490
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.276
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.031
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0136
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            43830
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         75.007
_diffrn_reflns_theta_min         4.502
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'κ-geometry four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'focusing mirror'
_diffrn_radiation_detector       'Bruker PHOTON II'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.865
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                5380
_reflns_number_total             5446
_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       'SAINT+ V8.40B (Bruker AXS Inc., 2020)'
_computing_data_collection       'APEX5 Ver.2022.08-RC130 (Bruker-AXS, 2023)'
_computing_data_reduction        'SAINT+ Ve8.40B (Bruker-AXS, 2020)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2019/1)'
_computing_structure_solution    'XT (Sheldrick, 2018/2)'
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 2479 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     378
_refine_ls_number_reflns         5446
_refine_ls_number_restraints     27
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0283
_refine_ls_restrained_S_all      1.036
_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)+(0.0484P)²+0.2443P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0775
_refine_ls_wR_factor_ref         0.0780
_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron density map and refined using anisotropic displacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv of the connected C atoms (1.5xUeqiv for methyl groups). Those H atoms
 attached to nitrogen and oxygen were located in Fourier diff maps and assigned Uiso = 1.2xUeqiv (1.5xUeqiv for Oxygen).
The isopropyl group exhibits two-part disorder with the occupancy refined to a 0.76:0.24 ratio.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C10B-C11B \\sim C10B-C11C
 with sigma of 0.02
 C11B-C12B \\sim C11C-C12C
 with sigma of 0.02
 C11B-C13B \\sim C11C-C13C
 with sigma of 0.02
 C10B-C12B \\sim C10B-C12C
 with sigma of 0.04
 C10B-C13B \\sim C10B-C13C
 with sigma of 0.04
 C12B-C13B \\sim C12C-C13C
 with sigma of 0.04
 N1B-H1B \\sim N1A-H1A
 with sigma of 0.02
 O2A-H2A \\sim O2B-H2B
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C11B, C12B, C13B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C11C, C12C, C13C
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Sof(H10C)=Sof(H10D)=Sof(C13C)=Sof(H13D)=Sof(H13E)=Sof(H13F)=Sof(C11C)=
 Sof(H11C)=Sof(C12C)=Sof(H12D)=Sof(H12E)=Sof(H12F)=1-FVAR(1)
 Sof(H10A)=Sof(H10B)=Sof(C11B)=Sof(H11B)=Sof(C12B)=Sof(H12A)=Sof(H12B)=
 Sof(H12C)=Sof(C13B)=Sof(H13A)=Sof(H13B)=Sof(H13C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C9A(H9A), C9B(H9B), C11B(H11B), C11C(H11C)
5.b Secondary CH2 refined with riding coordinates:
 C10A(H10E,H10F), C10B(H10A,H10B), C10B(H10C,H10D)
5.c Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C4A(H4A), C5A(H5A), C6A(H6A), C7A(H7A), C12A(H12G), C13A(H13G),
 C14A(H14A), C15A(H15A), C16A(H16A), C3B(H3B), C4B(H4B), C5B(H5B), C6B(H6B),
 C7B(H7B)
5.d Idealised Me refined as rotating group:
 C12B(H12A,H12B,H12C), C13B(H13A,H13B,H13C), C13C(H13D,H13E,H13F), C12C(H12D,
 H12E,H12F)
;
_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 0.53367(12) 0.19277(14) 0.91420(9) 0.0229(3) Uani 1 1 d . . . . .
O2A O 0.35337(12) 0.49806(16) 0.95451(9) 0.0256(3) Uani 1 1 d D . . . .
H2A H 0.398(2) 0.567(3) 1.0019(17) 0.038 Uiso 1 1 d D U . . .
O3A O 0.52085(11) 0.53352(14) 0.89758(8) 0.0196(3) Uani 1 1 d . . . . .
N1A N 0.43804(13) 0.29992(16) 0.76729(10) 0.0171(3) Uani 1 1 d D . . . .
H1A H 0.4534(19) 0.335(2) 0.7144(14) 0.020 Uiso 1 1 d D U . . .
C1A C 0.52906(15) 0.21338(17) 0.82643(11) 0.0176(3) Uani 1 1 d . . . . .
C2A C 0.62337(16) 0.14611(18) 0.78196(12) 0.0188(3) Uani 1 1 d . . . . .
C3A C 0.74309(17) 0.1025(2) 0.84458(13) 0.0266(4) Uani 1 1 d . . . . .
H3A H 0.763503 0.114930 0.914355 0.032 Uiso 1 1 calc R U . . .
C4A C 0.83233(18) 0.0410(3) 0.80517(15) 0.0324(4) Uani 1 1 d . . . . .
H4A H 0.913988 0.011290 0.848081 0.039 Uiso 1 1 calc R U . . .
C5A C 0.80344(18) 0.0224(2) 0.70356(15) 0.0292(4) Uani 1 1 d . . . . .
H5A H 0.865436 -0.019291 0.676956 0.035 Uiso 1 1 calc R U . . .
C6A C 0.68409(17) 0.0645(2) 0.64068(13) 0.0250(4) Uani 1 1 d . . . . .
H6A H 0.663901 0.050864 0.571024 0.030 Uiso 1 1 calc R U . . .
C7A C 0.59427(16) 0.12650(19) 0.67957(12) 0.0202(3) Uani 1 1 d . . . . .
H7A H 0.512615 0.155769 0.636439 0.024 Uiso 1 1 calc R U . . .
C8A C 0.41840(16) 0.47657(19) 0.89154(12) 0.0184(3) Uani 1 1 d . . . . .
C9A C 0.34750(16) 0.37462(19) 0.80654(12) 0.0181(3) Uani 1 1 d . . . . .
H9A H 0.297604 0.300642 0.831683 0.022 Uiso 1 1 calc R U . . .
C10A C 0.25365(16) 0.4665(2) 0.72395(12) 0.0199(3) Uani 1 1 d . . . . .
H10E H 0.205111 0.533001 0.754568 0.024 Uiso 1 1 calc R U . . .
H10F H 0.304220 0.527831 0.691883 0.024 Uiso 1 1 calc R U . . .
C11A C 0.15856(16) 0.37582(19) 0.64484(12) 0.0197(3) Uani 1 1 d . . . . .
C12A C 0.03466(16) 0.3521(2) 0.64996(13) 0.0251(4) Uani 1 1 d . . . . .
H12G H 0.011167 0.391534 0.703999 0.030 Uiso 1 1 calc R U . . .
C13A C -0.05495(16) 0.2719(2) 0.57755(14) 0.0287(4) Uani 1 1 d . . . . .
H13G H -0.139724 0.259415 0.581271 0.034 Uiso 1 1 calc R U . . .
C14A C -0.02112(16) 0.2102(2) 0.49999(13) 0.0282(4) Uani 1 1 d . . . . .
H14A H -0.081862 0.153790 0.450965 0.034 Uiso 1 1 calc R U . . .
C15A C 0.10195(17) 0.2313(2) 0.49434(12) 0.0267(4) Uani 1 1 d . . . . .
H15A H 0.125844 0.188352 0.441508 0.032 Uiso 1 1 calc R U . . .
C16A C 0.19114(16) 0.3151(2) 0.56555(12) 0.0225(4) Uani 1 1 d . . . . .
H16A H 0.274639 0.330923 0.559986 0.027 Uiso 1 1 calc R U . . .
O1B O 0.46777(11) 0.80334(14) 0.58863(8) 0.0209(3) Uani 1 1 d . . . . .
O2B O 0.64477(11) 0.50127(15) 0.54006(9) 0.0229(3) Uani 1 1 d D . . . .
H2B H 0.603(2) 0.436(3) 0.4921(17) 0.034 Uiso 1 1 d D U . . .
O3B O 0.48406(11) 0.45661(14) 0.60269(8) 0.0190(2) Uani 1 1 d . . . . .
N1B N 0.56636(13) 0.69214(16) 0.73317(10) 0.0168(3) Uani 1 1 d D . . . .
H1B H 0.5638(19) 0.657(2) 0.7906(14) 0.020 Uiso 1 1 d D U . . .
C1B C 0.47503(15) 0.78090(17) 0.67678(12) 0.0169(3) Uani 1 1 d . . . . .
C2B C 0.38419(16) 0.84910(18) 0.72409(12) 0.0176(3) Uani 1 1 d . . . . .
C3B C 0.27008(16) 0.9099(2) 0.66275(13) 0.0230(4) Uani 1 1 d . . . . .
H3B H 0.252377 0.907904 0.592713 0.028 Uiso 1 1 calc R U . . .
C4B C 0.18220(17) 0.9732(2) 0.70338(14) 0.0274(4) Uani 1 1 d . . . . .
H4B H 0.104744 1.014618 0.661196 0.033 Uiso 1 1 calc R U . . .
C5B C 0.20753(17) 0.9760(2) 0.80555(14) 0.0260(4) Uani 1 1 d . . . . .
H5B H 0.147160 1.019009 0.833269 0.031 Uiso 1 1 calc R U . . .
C6B C 0.32090(18) 0.9162(2) 0.86745(13) 0.0252(4) Uani 1 1 d . . . . .
H6B H 0.337798 0.917772 0.937405 0.030 Uiso 1 1 calc R U . . .
C7B C 0.40976(17) 0.8539(2) 0.82704(13) 0.0212(3) Uani 1 1 d . . . . .
H7B H 0.487975 0.814542 0.869516 0.025 Uiso 1 1 calc R U . . .
C8B C 0.58324(15) 0.51861(18) 0.60582(11) 0.0162(3) Uani 1 1 d . . . . .
C9B C 0.65599(15) 0.61974(19) 0.69080(11) 0.0169(3) Uani 1 1 d . . . . .
H9B H 0.704164 0.695062 0.665151 0.020 Uiso 1 1 calc R U . . .
C10B C 0.75169(16) 0.5272(2) 0.77103(12) 0.0219(4) Uani 1 1 d D . . . .
H10A H 0.802773 0.465689 0.739496 0.026 Uiso 0.764(5) 1 calc R U P A 1
H10B H 0.703160 0.461135 0.801950 0.026 Uiso 0.764(5) 1 calc R U P A 1
H10C H 0.700188 0.471425 0.805306 0.026 Uiso 0.236(5) 1 calc R U P A 2
H10D H 0.788742 0.454485 0.735708 0.026 Uiso 0.236(5) 1 calc R U P A 2
C11B C 0.8443(4) 0.6225(5) 0.8527(3) 0.0264(9) Uani 0.764(5) 1 d D . P A 1
H11B H 0.795355 0.709256 0.864969 0.032 Uiso 0.764(5) 1 calc R U P A 1
C12B C 0.8917(4) 0.5349(6) 0.9485(2) 0.0692(14) Uani 0.764(5) 1 d D . P A 1
H12A H 0.817930 0.504208 0.969235 0.104 Uiso 0.764(5) 1 calc R U P A 1
H12B H 0.949297 0.595863 1.000459 0.104 Uiso 0.764(5) 1 calc R U P A 1
H12C H 0.938467 0.448315 0.937456 0.104 Uiso 0.764(5) 1 calc R U P A 1
C13B C 0.9587(2) 0.6773(3) 0.8236(2) 0.0324(6) Uani 0.764(5) 1 d D . P A 1
H13A H 1.011024 0.593879 0.815548 0.049 Uiso 0.764(5) 1 calc R U P A 1
H13B H 1.011038 0.742337 0.875565 0.049 Uiso 0.764(5) 1 calc R U P A 1
H13C H 0.928055 0.731228 0.760806 0.049 Uiso 0.764(5) 1 calc R U P A 1
C13C C 0.9548(10) 0.4674(13) 0.9090(7) 0.048(3) Uani 0.236(5) 1 d D . P A 2
H13D H 0.912549 0.414952 0.950825 0.073 Uiso 0.236(5) 1 calc R U P A 2
H13E H 1.036354 0.508764 0.950834 0.073 Uiso 0.236(5) 1 calc R U P A 2
H13F H 0.971613 0.399309 0.861004 0.073 Uiso 0.236(5) 1 calc R U P A 2
C11C C 0.8648(16) 0.594(2) 0.8522(13) 0.047(4) Uani 0.236(5) 1 d D . P A 2
H11C H 0.914851 0.658193 0.820216 0.057 Uiso 0.236(5) 1 calc R U P A 2
C12C C 0.8201(9) 0.6833(12) 0.9227(7) 0.041(2) Uani 0.236(5) 1 d D . P A 2
H12D H 0.766410 0.764026 0.886911 0.061 Uiso 0.236(5) 1 calc R U P A 2
H12E H 0.894814 0.723108 0.974208 0.061 Uiso 0.236(5) 1 calc R U P A 2
H12F H 0.769655 0.621873 0.953703 0.061 Uiso 0.236(5) 1 calc R U P A 2


_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 C1A 1.243(2) . ?
O2A H2A 0.94(2) . ?
O2A C8A 1.315(2) . ?
O3A C8A 1.212(2) . ?
N1A H1A 0.876(17) . ?
N1A C1A 1.341(2) . ?
N1A C9A 1.446(2) . ?
C1A C2A 1.495(2) . ?
C2A C3A 1.392(2) . ?
C2A C7A 1.396(2) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.383(3) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.385(3) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.386(3) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.385(2) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.529(2) . ?
C9A H9A 1.0000 . ?
C9A C10A 1.543(2) . ?
C10A H10E 0.9900 . ?
C10A H10F 0.9900 . ?
C10A C11A 1.516(2) . ?
C11A C12A 1.394(2) . ?
C11A C16A 1.393(2) . ?
C12A H12G 0.9500 . ?
C12A C13A 1.387(3) . ?
C13A H13G 0.9500 . ?
C13A C14A 1.383(3) . ?
C14A H14A 0.9500 . ?
C14A C15A 1.384(3) . ?
C15A H15A 0.9500 . ?
C15A C16A 1.394(2) . ?
C16A H16A 0.9500 . ?
O1B C1B 1.243(2) . ?
O2B H2B 0.92(2) . ?
O2B C8B 1.3154(19) . ?
O3B C8B 1.211(2) . ?
N1B H1B 0.882(17) . ?
N1B C1B 1.340(2) . ?
N1B C9B 1.455(2) . ?
C1B C2B 1.494(2) . ?
C2B C3B 1.395(2) . ?
C2B C7B 1.398(2) . ?
C3B H3B 0.9500 . ?
C3B C4B 1.388(3) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.387(3) . ?
C5B H5B 0.9500 . ?
C5B C6B 1.389(3) . ?
C6B H6B 0.9500 . ?
C6B C7B 1.391(2) . ?
C7B H7B 0.9500 . ?
C8B C9B 1.530(2) . ?
C9B H9B 1.0000 . ?
C9B C10B 1.537(2) . ?
C10B H10A 0.9900 . ?
C10B H10B 0.9900 . ?
C10B H10C 0.9900 . ?
C10B H10D 0.9900 . ?
C10B C11B 1.548(4) . ?
C10B C11C 1.529(17) . ?
C11B H11B 1.0000 . ?
C11B C12B 1.521(5) . ?
C11B C13B 1.517(5) . ?
C12B H12A 0.9800 . ?
C12B H12B 0.9800 . ?
C12B H12C 0.9800 . ?
C13B H13A 0.9800 . ?
C13B H13B 0.9800 . ?
C13B H13C 0.9800 . ?
C13C H13D 0.9800 . ?
C13C H13E 0.9800 . ?
C13C H13F 0.9800 . ?
C13C C11C 1.569(18) . ?
C11C H11C 1.0000 . ?
C11C C12C 1.485(17) . ?
C12C H12D 0.9800 . ?
C12C H12E 0.9800 . ?
C12C H12F 0.9800 . ?

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
C8A O2A H2A 108.3(15) . . ?
C1A N1A H1A 116.6(14) . . ?
C1A N1A C9A 120.03(13) . . ?
C9A N1A H1A 119.3(14) . . ?
O1A C1A N1A 120.46(15) . . ?
O1A C1A C2A 122.61(15) . . ?
N1A C1A C2A 116.93(14) . . ?
C3A C2A C1A 118.86(15) . . ?
C3A C2A C7A 119.48(15) . . ?
C7A C2A C1A 121.66(15) . . ?
C2A C3A H3A 120.0 . . ?
C4A C3A C2A 119.95(17) . . ?
C4A C3A H3A 120.0 . . ?
C3A C4A H4A 119.8 . . ?
C3A C4A C5A 120.44(17) . . ?
C5A C4A H4A 119.8 . . ?
C4A C5A H5A 120.0 . . ?
C4A C5A C6A 120.01(17) . . ?
C6A C5A H5A 120.0 . . ?
C5A C6A H6A 120.1 . . ?
C7A C6A C5A 119.90(17) . . ?
C7A C6A H6A 120.1 . . ?
C2A C7A H7A 119.9 . . ?
C6A C7A C2A 120.22(16) . . ?
C6A C7A H7A 119.9 . . ?
O2A C8A C9A 112.12(14) . . ?
O3A C8A O2A 124.61(15) . . ?
O3A C8A C9A 123.24(14) . . ?
N1A C9A C8A 110.49(13) . . ?
N1A C9A H9A 109.3 . . ?
N1A C9A C10A 109.74(13) . . ?
C8A C9A H9A 109.3 . . ?
C8A C9A C10A 108.74(14) . . ?
C10A C9A H9A 109.3 . . ?
C9A C10A H10E 108.8 . . ?
C9A C10A H10F 108.8 . . ?
H10E C10A H10F 107.7 . . ?
C11A C10A C9A 113.92(15) . . ?
C11A C10A H10E 108.8 . . ?
C11A C10A H10F 108.8 . . ?
C12A C11A C10A 120.02(15) . . ?
C16A C11A C10A 121.71(15) . . ?
C16A C11A C12A 118.28(16) . . ?
C11A C12A H12G 119.4 . . ?
C13A C12A C11A 121.17(16) . . ?
C13A C12A H12G 119.4 . . ?
C12A C13A H13G 119.9 . . ?
C14A C13A C12A 120.12(16) . . ?
C14A C13A H13G 119.9 . . ?
C13A C14A H14A 120.3 . . ?
C13A C14A C15A 119.45(16) . . ?
C15A C14A H14A 120.3 . . ?
C14A C15A H15A 119.7 . . ?
C14A C15A C16A 120.54(16) . . ?
C16A C15A H15A 119.7 . . ?
C11A C16A C15A 120.40(16) . . ?
C11A C16A H16A 119.8 . . ?
C15A C16A H16A 119.8 . . ?
C8B O2B H2B 111.1(15) . . ?
C1B N1B H1B 122.5(14) . . ?
C1B N1B C9B 120.02(13) . . ?
C9B N1B H1B 115.7(14) . . ?
O1B C1B N1B 120.17(15) . . ?
O1B C1B C2B 122.45(15) . . ?
N1B C1B C2B 117.37(14) . . ?
C3B C2B C1B 118.40(14) . . ?
C3B C2B C7B 119.27(15) . . ?
C7B C2B C1B 122.32(15) . . ?
C2B C3B H3B 119.8 . . ?
C4B C3B C2B 120.42(16) . . ?
C4B C3B H3B 119.8 . . ?
C3B C4B H4B 120.0 . . ?
C5B C4B C3B 119.98(17) . . ?
C5B C4B H4B 120.0 . . ?
C4B C5B H5B 119.9 . . ?
C4B C5B C6B 120.16(16) . . ?
C6B C5B H5B 119.9 . . ?
C5B C6B H6B 120.0 . . ?
C5B C6B C7B 120.02(16) . . ?
C7B C6B H6B 120.0 . . ?
C2B C7B H7B 119.9 . . ?
C6B C7B C2B 120.14(16) . . ?
C6B C7B H7B 119.9 . . ?
O2B C8B C9B 112.02(13) . . ?
O3B C8B O2B 124.38(15) . . ?
O3B C8B C9B 123.51(14) . . ?
N1B C9B C8B 110.30(12) . . ?
N1B C9B H9B 109.5 . . ?
N1B C9B C10B 109.58(12) . . ?
C8B C9B H9B 109.5 . . ?
C8B C9B C10B 108.55(14) . . ?
C10B C9B H9B 109.5 . . ?
C9B C10B H10A 109.1 . . ?
C9B C10B H10B 109.1 . . ?
C9B C10B H10C 106.6 . . ?
C9B C10B H10D 106.6 . . ?
C9B C10B C11B 112.4(2) . . ?
H10A C10B H10B 107.9 . . ?
H10C C10B H10D 106.6 . . ?
C11B C10B H10A 109.1 . . ?
C11B C10B H10B 109.1 . . ?
C11C C10B C9B 122.8(8) . . ?
C11C C10B H10C 106.6 . . ?
C11C C10B H10D 106.6 . . ?
C10B C11B H11B 108.4 . . ?
C12B C11B C10B 109.5(3) . . ?
C12B C11B H11B 108.4 . . ?
C13B C11B C10B 112.6(3) . . ?
C13B C11B H11B 108.4 . . ?
C13B C11B C12B 109.5(3) . . ?
C11B C12B H12A 109.5 . . ?
C11B C12B H12B 109.5 . . ?
C11B C12B H12C 109.5 . . ?
H12A C12B H12B 109.5 . . ?
H12A C12B H12C 109.5 . . ?
H12B C12B H12C 109.5 . . ?
C11B C13B H13A 109.5 . . ?
C11B C13B H13B 109.5 . . ?
C11B C13B H13C 109.5 . . ?
H13A C13B H13B 109.5 . . ?
H13A C13B H13C 109.5 . . ?
H13B C13B H13C 109.5 . . ?
H13D C13C H13E 109.5 . . ?
H13D C13C H13F 109.5 . . ?
H13E C13C H13F 109.5 . . ?
C11C C13C H13D 109.5 . . ?
C11C C13C H13E 109.5 . . ?
C11C C13C H13F 109.5 . . ?
C10B C11C C13C 108.9(13) . . ?
C10B C11C H11C 108.7 . . ?
C13C C11C H11C 108.7 . . ?
C12C C11C C10B 111.6(11) . . ?
C12C C11C C13C 110.1(13) . . ?
C12C C11C H11C 108.7 . . ?
C11C C12C H12D 109.5 . . ?
C11C C12C H12E 109.5 . . ?
C11C C12C H12F 109.5 . . ?
H12D C12C H12E 109.5 . . ?
H12D C12C H12F 109.5 . . ?
H12E C12C H12F 109.5 . . ?

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
O2A H2A O1A 0.94(2) 1.65(2) 2.5927(18) 176(2) 2_657 yes
N1A H1A O3B 0.876(17) 2.044(18) 2.9080(18) 168(2) . yes
O2B H2B O1B 0.92(2) 1.68(2) 2.5912(17) 175(3) 2_646 yes
N1B H1B O3A 0.882(17) 2.057(18) 2.9122(18) 163(2) . 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
O1A C1A C2A C3A -22.7(2) . . . . ?
O1A C1A C2A C7A 157.41(17) . . . . ?
O2A C8A C9A N1A -153.38(14) . . . . ?
O2A C8A C9A C10A 86.12(17) . . . . ?
O3A C8A C9A N1A 28.6(2) . . . . ?
O3A C8A C9A C10A -91.87(19) . . . . ?
N1A C1A C2A C3A 156.59(16) . . . . ?
N1A C1A C2A C7A -23.3(2) . . . . ?
N1A C9A C10A C11A 70.63(17) . . . . ?
C1A N1A C9A C8A 60.06(19) . . . . ?
C1A N1A C9A C10A 179.96(14) . . . . ?
C1A C2A C3A C4A -179.52(18) . . . . ?
C1A C2A C7A C6A 179.66(16) . . . . ?
C2A C3A C4A C5A 0.0(3) . . . . ?
C3A C2A C7A C6A -0.2(3) . . . . ?
C3A C4A C5A C6A -0.5(3) . . . . ?
C4A C5A C6A C7A 0.6(3) . . . . ?
C5A C6A C7A C2A -0.3(3) . . . . ?
C7A C2A C3A C4A 0.3(3) . . . . ?
C8A C9A C10A C11A -168.42(13) . . . . ?
C9A N1A C1A O1A 2.4(2) . . . . ?
C9A N1A C1A C2A -176.89(14) . . . . ?
C9A C10A C11A C12A 97.32(19) . . . . ?
C9A C10A C11A C16A -83.1(2) . . . . ?
C10A C11A C12A C13A 178.76(17) . . . . ?
C10A C11A C16A C15A 179.52(17) . . . . ?
C11A C12A C13A C14A 1.9(3) . . . . ?
C12A C11A C16A C15A -0.9(3) . . . . ?
C12A C13A C14A C15A -1.1(3) . . . . ?
C13A C14A C15A C16A -0.6(3) . . . . ?
C14A C15A C16A C11A 1.6(3) . . . . ?
C16A C11A C12A C13A -0.9(3) . . . . ?
O1B C1B C2B C3B 16.0(2) . . . . ?
O1B C1B C2B C7B -164.00(17) . . . . ?
O2B C8B C9B N1B 152.63(14) . . . . ?
O2B C8B C9B C10B -87.30(16) . . . . ?
O3B C8B C9B N1B -30.8(2) . . . . ?
O3B C8B C9B C10B 89.27(18) . . . . ?
N1B C1B C2B C3B -163.67(15) . . . . ?
N1B C1B C2B C7B 16.3(2) . . . . ?
N1B C9B C10B C11B -68.1(2) . . . . ?
N1B C9B C10B C11C -76.6(9) . . . . ?
C1B N1B C9B C8B -61.58(19) . . . . ?
C1B N1B C9B C10B 178.97(15) . . . . ?
C1B C2B C3B C4B 179.40(16) . . . . ?
C1B C2B C7B C6B -178.77(17) . . . . ?
C2B C3B C4B C5B -0.1(3) . . . . ?
C3B C2B C7B C6B 1.2(3) . . . . ?
C3B C4B C5B C6B 0.3(3) . . . . ?
C4B C5B C6B C7B 0.3(3) . . . . ?
C5B C6B C7B C2B -1.1(3) . . . . ?
C7B C2B C3B C4B -0.6(3) . . . . ?
C8B C9B C10B C11B 171.3(2) . . . . ?
C8B C9B C10B C11C 162.9(9) . . . . ?
C9B N1B C1B O1B -1.1(2) . . . . ?
C9B N1B C1B C2B 178.61(14) . . . . ?
C9B C10B C11B C12B 154.6(3) . . . . ?
C9B C10B C11B C13B -83.3(3) . . . . ?
C9B C10B C11C C13C -170.4(7) . . . . ?
C9B C10B C11C C12C 67.9(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
####################################################################### 
# 
# 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_22kaw06_a
_database_code_depnum_ccdc_archive 'CCDC 2312815'
loop_
_audit_author_name
_audit_author_address
'Kraig Wheeler'
;Whitworth University
United States of America
;
_audit_update_record             
;
2023-12-08 deposited with the CCDC.	2024-02-12 downloaded from the CCDC.
;
_audit_creation_date             2023-11-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H16 F3 N O3, C16 H15 N O3'
_chemical_formula_sum            'C30 H31 F3 N2 O6'
_chemical_formula_weight         572.57
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.4316(8)
_cell_length_b                   9.5763(6)
_cell_length_c                   14.2272(10)
_cell_angle_alpha                90
_cell_angle_beta                 111.456(3)
_cell_angle_gamma                90
_cell_volume                     1449.55(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9928
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.23
_cell_measurement_theta_min      3.34
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.880
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             600
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 0.00 -1.00 0.0090
-1.00 0.00 0.00 0.0100
-1.00 -1.00 -1.00 0.0730
0.00 0.00 1.00 0.0400
0.00 0.00 -1.00 0.0390
0.00 1.00 -1.00 0.0930
0.00 -1.00 1.00 0.0860
1.00 0.00 1.00 0.0410
1.00 0.00 -1.00 0.0490

_exptl_crystal_size_max          0.289
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            38681
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.378
_diffrn_reflns_theta_min         3.338
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'κ-geometry four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'focusing mirror'
_diffrn_radiation_detector       'Bruker PHOTON II'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.870
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                5522
_reflns_number_total             5688
_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       'SAINT+ V8.40B (Bruker AXS Inc., 2020)'
_computing_data_collection       'APEX5 Ver.2022.08-RC130 (Bruker-AXS, 2023)'
_computing_data_reduction        'SAINT+ Ve8.40B (Bruker-AXS, 2020)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2019/1)'
_computing_structure_solution    'XT (Sheldrick, 2018/2)'
_refine_diff_density_max         0.874
_refine_diff_density_min         -0.801
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 2494 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     414
_refine_ls_number_reflns         5688
_refine_ls_number_restraints     82
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0479
_refine_ls_restrained_S_all      1.153
_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)+(0.0592P)²+1.1181P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1206
_refine_ls_wR_factor_ref         0.1221
_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron density map and refined using anisotropic displacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv of the connected C atoms (1.5xUeqiv for methyl groups). Those H atoms
 attached to nitrogen and oxygen were located in Fourier diff maps and assigned Uiso = 1.2xUeqiv nitrogen (1.5xUeqiv for oxygen). 
The isopropyl group was modeled with two part disorder with the occupancies refined to 83:17. The CF3 group is also disordered and modeled with three-part disorder. The occupancies of these parts were refined and found exist in nearly a 1:1:1 ratio. Restraints were applied to the CF3 and isopropyl groups.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 F1A-F2A \\sim F2A-F3A \\sim F3A-F1A
 with sigma of 0.001
 C14A-F1A \\sim C14A-F2A \\sim C14A-F3A
 with sigma of 0.001
 C14A-F1B \\sim C14A-F2B \\sim C14A-F3B
 with sigma of 0.001
 C14A-F1C \\sim C14A-F2C \\sim C14A-F3C
 with sigma of 0.001
 C5A-F1A \\sim C5A-F2A \\sim C5A-F3A
 with sigma of 0.001
3. Rigid bond restraints
 F1A, F2A, F3A, F1B, F2B, F3B, F1C, F2C, F3C
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
4. Uiso/Uaniso restraints and constraints
Uanis(F1C) \\sim Ueq, Uanis(F2C) \\sim Ueq, Uanis(F3C) \\sim Ueq, Uanis(F1A)
\\sim Ueq, Uanis(F2A) \\sim Ueq, Uanis(F3A) \\sim Ueq, Uanis(F1B) \\sim Ueq,
Uanis(F2B) \\sim Ueq, Uanis(F3B) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
Uanis(F1A) = Uanis(F1B)
Uanis(F2A) = Uanis(F2B)
Uanis(F3A) = Uanis(F3B)
Uanis(C11A) = Uanis(C11C)
Uanis(C12A) = Uanis(C12C)
Uanis(C13A) = Uanis(C13C)
Uanis(F1A) = Uanis(F1C)
Uanis(F2A) = Uanis(F2C)
Uanis(F3A) = Uanis(F3C)
5. Rigid body (RIGU) restrains
 F1A, F2A, F3A, F1B, F2B, F3B, F1C, F2C, F3C
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
6. Same fragment restrains
{C11A, C12A, C13A} sigma for 1-2: 0.02, 1-3: 0.04
as in
{C11C, C12C, C13C}
{F1B, F2B, F3B} sigma for 1-2: 0.01, 1-3: 0.02
{F1C, F2C, F3C} sigma for 1-2: 0.01, 1-3: 0.02
as in
{F1A, F2A, F3A}
7. Others
 Sof(H10A)=Sof(H10B)=Sof(C11A)=Sof(H11A)=Sof(C12A)=Sof(H12A)=Sof(H12B)=
 Sof(H12C)=Sof(C13A)=Sof(H13A)=Sof(H13B)=Sof(H13C)=1-FVAR(1)
 Sof(H10C)=Sof(H10D)=Sof(C11C)=Sof(H11C)=Sof(C12C)=Sof(H12D)=Sof(H12E)=
 Sof(H12F)=Sof(C13C)=Sof(H13D)=Sof(H13E)=Sof(H13F)=FVAR(1)
 Fixed Sof: F1A(0.333333) F2A(0.333333) F3A(0.333333) F1B(0.333333)
 F2B(0.333333) F3B(0.333333) F1C(0.333333) F2C(0.333333) F3C(0.333333)
8.a Ternary CH refined with riding coordinates:
 C9A(H9A), C11A(H11A), C11C(H11C), C9B(HG)
8.b Secondary CH2 refined with riding coordinates:
 C10A(H10A,H10B), C10A(H10C,H10D), C10B(HH,HI)
8.c Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C4A(H4A), C6A(H6A), C7A(H7A), C3B(HB), C4B(HC), C5B(HD), C6B(HE),
 C7B(HF), C12B(HJ), C13B(HK), C14B(HL), C15B(HM), C16B(HN)
8.d Idealised Me refined as rotating group:
 C12A(H12A,H12B,H12C), C13A(H13A,H13B,H13C), C12C(H12D,H12E,H12F), C13C(H13D,
 H13E,H13F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 0.5045(2) 0.3119(3) 0.58993(17) 0.0234(5) Uani 1 1 d . . . . .
O2A O 0.6334(2) 0.6320(3) 0.54035(18) 0.0266(5) Uani 1 1 d . . . . .
H2A H 0.581(4) 0.685(5) 0.495(4) 0.040 Uiso 1 1 d . U . . .
O3A O 0.4799(2) 0.6367(3) 0.60260(16) 0.0200(5) Uani 1 1 d . . . . .
N1A N 0.5978(2) 0.4260(3) 0.7359(2) 0.0179(5) Uani 1 1 d . . . . .
H1A H 0.588(4) 0.466(4) 0.790(3) 0.021 Uiso 1 1 d . U . . .
C1A C 0.5128(3) 0.3345(4) 0.6780(2) 0.0188(6) Uani 1 1 d . . . . .
C2A C 0.4279(3) 0.2667(4) 0.7228(2) 0.0191(6) Uani 1 1 d . . . . .
C3A C 0.3088(3) 0.2254(4) 0.6590(2) 0.0248(7) Uani 1 1 d . . . . .
H3A H 0.285044 0.235187 0.588021 0.030 Uiso 1 1 calc R U . . .
C4A C 0.2242(3) 0.1699(5) 0.6984(3) 0.0304(8) Uani 1 1 d . . . . .
H4A H 0.143242 0.140041 0.654843 0.036 Uiso 1 1 calc R U . . .
C5A C 0.2593(3) 0.1588(4) 0.8018(2) 0.0259(7) Uani 1 1 d D . . . .
C6A C 0.3799(3) 0.1939(4) 0.8666(2) 0.0230(7) Uani 1 1 d . . . . .
H6A H 0.404130 0.180309 0.937347 0.028 Uiso 1 1 calc R U . . .
C7A C 0.4645(3) 0.2488(4) 0.8273(2) 0.0194(6) Uani 1 1 d . . . . .
H7A H 0.546784 0.274181 0.870970 0.023 Uiso 1 1 calc R U . . .
C8A C 0.5823(3) 0.5981(4) 0.6065(2) 0.0183(6) Uani 1 1 d . . . . .
C9A C 0.6709(3) 0.5078(4) 0.6915(2) 0.0191(6) Uani 1 1 d . . . . .
H9A H 0.716759 0.442603 0.662150 0.023 Uiso 1 1 calc R U . . .
C10A C 0.7677(3) 0.6017(4) 0.7700(2) 0.0213(6) Uani 1 1 d . . . . .
H10A H 0.803090 0.667894 0.733941 0.026 Uiso 0.163(8) 1 calc R U P A 1
H10B H 0.723678 0.657261 0.805638 0.026 Uiso 0.163(8) 1 calc R U P A 1
H10C H 0.779350 0.687353 0.735414 0.026 Uiso 0.837(8) 1 calc R U P A 2
H10D H 0.732314 0.630398 0.820982 0.026 Uiso 0.837(8) 1 calc R U P A 2
C14A C 0.1701(3) 0.10150(13) 0.84664(18) 0.0374(9) Uani 1 1 d D . . . .
F1A F 0.0525(5) 0.0813(6) 0.7793(5) 0.0496(12) Uani 0.3333 1 d D U P B 1
F2A F 0.1560(6) 0.1824(6) 0.9194(4) 0.0366(11) Uani 0.3333 1 d D U P B 1
F3A F 0.2049(6) -0.0248(5) 0.8912(4) 0.0498(12) Uani 0.3333 1 d D U P B 1
C11A C 0.876(3) 0.523(3) 0.848(2) 0.0256(10) Uani 0.163(8) 1 d D . P A 1
H11A H 0.842464 0.470469 0.893953 0.031 Uiso 0.163(8) 1 calc R U P A 1
C12A C 0.965(4) 0.639(5) 0.910(3) 0.0332(14) Uani 0.163(8) 1 d D . P A 1
H12A H 0.927671 0.685084 0.953372 0.050 Uiso 0.163(8) 1 calc R U P A 1
H12B H 0.977832 0.707530 0.863151 0.050 Uiso 0.163(8) 1 calc R U P A 1
H12C H 1.045908 0.597749 0.950988 0.050 Uiso 0.163(8) 1 calc R U P A 1
C13A C 0.943(2) 0.421(3) 0.803(2) 0.0429(13) Uani 0.163(8) 1 d D . P A 1
H13A H 0.887013 0.343032 0.771611 0.064 Uiso 0.163(8) 1 calc R U P A 1
H13B H 1.018506 0.384957 0.857023 0.064 Uiso 0.163(8) 1 calc R U P A 1
H13C H 0.967728 0.468920 0.752563 0.064 Uiso 0.163(8) 1 calc R U P A 1
F1B F 0.0504(6) 0.1398(9) 0.7886(6) 0.0496(12) Uani 0.3333 1 d D U P B 2
F2B F 0.1912(11) 0.1659(9) 0.9369(4) 0.0366(11) Uani 0.3333 1 d D U P B 2
F3B F 0.1819(9) -0.0392(5) 0.8622(7) 0.0498(12) Uani 0.3333 1 d D U P B 2
C11C C 0.8974(5) 0.5357(5) 0.8253(4) 0.0256(10) Uani 0.837(8) 1 d D . P A 2
H11C H 0.932409 0.506617 0.773378 0.031 Uiso 0.837(8) 1 calc R U P A 2
C12C C 0.9869(7) 0.6432(8) 0.8944(5) 0.0332(14) Uani 0.837(8) 1 d D . P A 2
H12D H 1.071684 0.603606 0.922862 0.050 Uiso 0.837(8) 1 calc R U P A 2
H12E H 0.958126 0.667679 0.949328 0.050 Uiso 0.837(8) 1 calc R U P A 2
H12F H 0.988176 0.727169 0.855476 0.050 Uiso 0.837(8) 1 calc R U P A 2
C13C C 0.8897(5) 0.4062(6) 0.8855(4) 0.0429(13) Uani 0.837(8) 1 d D . P A 2
H13D H 0.843547 0.332405 0.838936 0.064 Uiso 0.837(8) 1 calc R U P A 2
H13E H 0.845755 0.429621 0.931062 0.064 Uiso 0.837(8) 1 calc R U P A 2
H13F H 0.974713 0.373455 0.925110 0.064 Uiso 0.837(8) 1 calc R U P A 2
F1C F 0.0659(6) 0.1817(8) 0.8089(7) 0.0496(12) Uani 0.3333 1 d D U P B 3
F2C F 0.1978(11) 0.1354(10) 0.9445(4) 0.0366(11) Uani 0.3333 1 d D U P B 3
F3C F 0.1233(9) -0.0280(6) 0.8206(7) 0.0498(12) Uani 0.3333 1 d D U P B 3
O1B O 0.5163(2) 0.8783(3) 0.91631(16) 0.0209(5) Uani 1 1 d . . . . .
O2B O 0.3577(2) 0.5545(3) 0.94428(17) 0.0236(5) Uani 1 1 d . . . . .
H H 0.403(4) 0.498(5) 0.988(3) 0.035 Uiso 1 1 d . U . . .
O3B O 0.5235(2) 0.5502(3) 0.89603(16) 0.0198(5) Uani 1 1 d . . . . .
N1B N 0.4263(2) 0.7711(3) 0.7668(2) 0.0179(5) Uani 1 1 d . . . . .
HA H 0.440(4) 0.740(4) 0.718(3) 0.021 Uiso 1 1 d . U . . .
C1B C 0.5119(3) 0.8580(3) 0.8287(2) 0.0163(6) Uani 1 1 d . . . . .
C2B C 0.6006(3) 0.9253(4) 0.7878(2) 0.0176(6) Uani 1 1 d . . . . .
C3B C 0.5682(3) 0.9482(4) 0.6847(2) 0.0207(6) Uani 1 1 d . . . . .
HB H 0.486759 0.923606 0.638931 0.025 Uiso 1 1 calc R U . . .
C4B C 0.6544(3) 1.0065(4) 0.6486(3) 0.0261(7) Uani 1 1 d . . . . .
HC H 0.632658 1.020574 0.578101 0.031 Uiso 1 1 calc R U . . .
C5B C 0.7732(4) 1.0444(4) 0.7159(3) 0.0307(8) Uani 1 1 d . . . . .
HD H 0.832099 1.085979 0.691532 0.037 Uiso 1 1 calc R U . . .
C6B C 0.8056(3) 1.0215(5) 0.8190(3) 0.0307(8) Uani 1 1 d . . . . .
HE H 0.887147 1.045839 0.864743 0.037 Uiso 1 1 calc R U . . .
C7B C 0.7199(3) 0.9636(4) 0.8549(3) 0.0249(7) Uani 1 1 d . . . . .
HF H 0.741813 0.949576 0.925376 0.030 Uiso 1 1 calc R U . . .
C8B C 0.4199(3) 0.5914(4) 0.8864(2) 0.0173(6) Uani 1 1 d . . . . .
C9B C 0.3437(3) 0.6929(4) 0.8035(2) 0.0166(6) Uani 1 1 d . . . . .
HG H 0.298044 0.759400 0.832171 0.020 Uiso 1 1 calc R U . . .
C10B C 0.2466(3) 0.6112(4) 0.7158(2) 0.0203(6) Uani 1 1 d . . . . .
HH H 0.291565 0.549797 0.684222 0.024 Uiso 1 1 calc R U . . .
HI H 0.195868 0.551235 0.742916 0.024 Uiso 1 1 calc R U . . .
C11B C 0.1602(3) 0.7073(4) 0.6364(2) 0.0213(6) Uani 1 1 d . . . . .
C12B C 0.0535(4) 0.7613(5) 0.6473(3) 0.0377(9) Uani 1 1 d . . . . .
HJ H 0.033908 0.735654 0.704422 0.045 Uiso 1 1 calc R U . . .
C13B C -0.0256(4) 0.8525(6) 0.5759(4) 0.0544(13) Uani 1 1 d . . . . .
HK H -0.098428 0.888723 0.584426 0.065 Uiso 1 1 calc R U . . .
C14B C 0.0022(5) 0.8901(5) 0.4927(4) 0.0536(12) Uani 1 1 d . . . . .
HL H -0.050900 0.953041 0.444140 0.064 Uiso 1 1 calc R U . . .
C15B C 0.1063(4) 0.8361(6) 0.4807(4) 0.0534(13) Uani 1 1 d . . . . .
HM H 0.125305 0.861391 0.423296 0.064 Uiso 1 1 calc R U . . .
C16B C 0.1850(3) 0.7445(5) 0.5518(3) 0.0371(9) Uani 1 1 d . . . . .
HN H 0.256692 0.707111 0.541974 0.044 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
O1A C1A 1.241(4) . ?
O2A H2A 0.87(5) . ?
O2A C8A 1.317(4) . ?
O3A C8A 1.210(4) . ?
N1A H1A 0.90(4) . ?
N1A C1A 1.344(4) . ?
N1A C9A 1.449(4) . ?
C1A C2A 1.490(4) . ?
C2A C3A 1.389(4) . ?
C2A C7A 1.400(4) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.389(5) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.379(5) . ?
C5A C6A 1.391(5) . ?
C5A C14A 1.491(5) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.386(5) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.530(4) . ?
C9A H9A 1.0000 . ?
C9A C10A 1.542(4) . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C10A H10C 0.9900 . ?
C10A H10D 0.9900 . ?
C10A C11A 1.53(3) . ?
C10A C11C 1.537(6) . ?
C14A F1A 1.350(5) . ?
C14A F2A 1.349(5) . ?
C14A F3A 1.355(5) . ?
C14A F1B 1.365(5) . ?
C14A F2B 1.364(5) . ?
C14A F3B 1.364(5) . ?
C14A F1C 1.353(5) . ?
C14A F2C 1.350(5) . ?
C14A F3C 1.348(5) . ?
C11A H11A 1.0000 . ?
C11A C12A 1.54(2) . ?
C11A C13A 1.52(2) . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A H12C 0.9800 . ?
C13A H13A 0.9800 . ?
C13A H13B 0.9800 . ?
C13A H13C 0.9800 . ?
C11C H11C 1.0000 . ?
C11C C12C 1.529(6) . ?
C11C C13C 1.528(7) . ?
C12C H12D 0.9800 . ?
C12C H12E 0.9800 . ?
C12C H12F 0.9800 . ?
C13C H13D 0.9800 . ?
C13C H13E 0.9800 . ?
C13C H13F 0.9800 . ?
O1B C1B 1.245(4) . ?
O2B H 0.85(5) . ?
O2B C8B 1.318(4) . ?
O3B C8B 1.207(4) . ?
N1B HA 0.83(4) . ?
N1B C1B 1.340(4) . ?
N1B C9B 1.445(4) . ?
C1B C2B 1.487(4) . ?
C2B C3B 1.394(4) . ?
C2B C7B 1.397(5) . ?
C3B HB 0.9500 . ?
C3B C4B 1.384(5) . ?
C4B HC 0.9500 . ?
C4B C5B 1.394(5) . ?
C5B HD 0.9500 . ?
C5B C6B 1.393(5) . ?
C6B HE 0.9500 . ?
C6B C7B 1.377(5) . ?
C7B HF 0.9500 . ?
C8B C9B 1.531(4) . ?
C9B HG 1.0000 . ?
C9B C10B 1.545(4) . ?
C10B HH 0.9900 . ?
C10B HI 0.9900 . ?
C10B C11B 1.511(4) . ?
C11B C12B 1.385(5) . ?
C11B C16B 1.380(5) . ?
C12B HJ 0.9500 . ?
C12B C13B 1.393(6) . ?
C13B HK 0.9500 . ?
C13B C14B 1.381(8) . ?
C14B HL 0.9500 . ?
C14B C15B 1.365(8) . ?
C15B HM 0.9500 . ?
C15B C16B 1.391(6) . ?
C16B HN 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
C8A O2A H2A 109(3) . . ?
C1A N1A H1A 121(3) . . ?
C1A N1A C9A 119.2(3) . . ?
C9A N1A H1A 115(3) . . ?
O1A C1A N1A 120.3(3) . . ?
O1A C1A C2A 122.3(3) . . ?
N1A C1A C2A 117.4(3) . . ?
C3A C2A C1A 118.7(3) . . ?
C3A C2A C7A 120.0(3) . . ?
C7A C2A C1A 121.2(3) . . ?
C2A C3A H3A 119.8 . . ?
C4A C3A C2A 120.4(3) . . ?
C4A C3A H3A 119.8 . . ?
C3A C4A H4A 120.5 . . ?
C5A C4A C3A 119.1(3) . . ?
C5A C4A H4A 120.5 . . ?
C4A C5A C6A 121.3(3) . . ?
C4A C5A C14A 120.5(3) . . ?
C6A C5A C14A 118.2(3) . . ?
C5A C6A H6A 120.2 . . ?
C7A C6A C5A 119.5(3) . . ?
C7A C6A H6A 120.2 . . ?
C2A C7A H7A 120.2 . . ?
C6A C7A C2A 119.6(3) . . ?
C6A C7A H7A 120.2 . . ?
O2A C8A C9A 111.5(3) . . ?
O3A C8A O2A 124.5(3) . . ?
O3A C8A C9A 123.9(3) . . ?
N1A C9A C8A 109.3(2) . . ?
N1A C9A H9A 108.6 . . ?
N1A C9A C10A 112.1(3) . . ?
C8A C9A H9A 108.6 . . ?
C8A C9A C10A 109.6(3) . . ?
C10A C9A H9A 108.6 . . ?
C9A C10A H10A 108.6 . . ?
C9A C10A H10B 108.6 . . ?
C9A C10A H10C 108.4 . . ?
C9A C10A H10D 108.4 . . ?
H10A C10A H10B 107.6 . . ?
H10C C10A H10D 107.4 . . ?
C11A C10A C9A 114.5(11) . . ?
C11A C10A H10A 108.6 . . ?
C11A C10A H10B 108.6 . . ?
C11C C10A C9A 115.7(3) . . ?
C11C C10A H10C 108.4 . . ?
C11C C10A H10D 108.4 . . ?
F1A C14A C5A 114.1(3) . . ?
F1A C14A F3A 104.4(3) . . ?
F2A C14A C5A 114.2(3) . . ?
F2A C14A F1A 105.0(3) . . ?
F2A C14A F3A 104.5(3) . . ?
F3A C14A C5A 113.5(3) . . ?
F1B C14A C5A 109.4(5) . . ?
F2B C14A C5A 108.9(6) . . ?
F2B C14A F1B 104.0(6) . . ?
F3B C14A C5A 113.0(5) . . ?
F3B C14A F1B 112.4(6) . . ?
F3B C14A F2B 108.7(6) . . ?
F1C C14A C5A 105.2(5) . . ?
F2C C14A C5A 114.5(6) . . ?
F2C C14A F1C 96.5(6) . . ?
F3C C14A C5A 119.1(4) . . ?
F3C C14A F1C 102.1(6) . . ?
F3C C14A F2C 115.1(6) . . ?
C10A C11A H11A 108.9 . . ?
C10A C11A C12A 104(3) . . ?
C12A C11A H11A 108.9 . . ?
C13A C11A C10A 114(2) . . ?
C13A C11A H11A 108.9 . . ?
C13A C11A C12A 112(2) . . ?
C11A C12A H12A 109.5 . . ?
C11A C12A H12B 109.5 . . ?
C11A C12A H12C 109.5 . . ?
H12A C12A H12B 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C11A C13A H13A 109.5 . . ?
C11A C13A H13B 109.5 . . ?
C11A C13A H13C 109.5 . . ?
H13A C13A H13B 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C10A C11C H11C 108.0 . . ?
C12C C11C C10A 110.2(5) . . ?
C12C C11C H11C 108.0 . . ?
C13C C11C C10A 112.2(4) . . ?
C13C C11C H11C 108.0 . . ?
C13C C11C C12C 110.4(4) . . ?
C11C C12C H12D 109.5 . . ?
C11C C12C H12E 109.5 . . ?
C11C C12C H12F 109.5 . . ?
H12D C12C H12E 109.5 . . ?
H12D C12C H12F 109.5 . . ?
H12E C12C H12F 109.5 . . ?
C11C C13C H13D 109.5 . . ?
C11C C13C H13E 109.5 . . ?
C11C C13C H13F 109.5 . . ?
H13D C13C H13E 109.5 . . ?
H13D C13C H13F 109.5 . . ?
H13E C13C H13F 109.5 . . ?
C8B O2B H 108(3) . . ?
C1B N1B HA 118(3) . . ?
C1B N1B C9B 120.1(3) . . ?
C9B N1B HA 118(3) . . ?
O1B C1B N1B 120.5(3) . . ?
O1B C1B C2B 122.7(3) . . ?
N1B C1B C2B 116.8(3) . . ?
C3B C2B C1B 121.6(3) . . ?
C3B C2B C7B 119.7(3) . . ?
C7B C2B C1B 118.8(3) . . ?
C2B C3B HB 119.9 . . ?
C4B C3B C2B 120.2(3) . . ?
C4B C3B HB 119.9 . . ?
C3B C4B HC 120.1 . . ?
C3B C4B C5B 119.8(3) . . ?
C5B C4B HC 120.1 . . ?
C4B C5B HD 120.0 . . ?
C6B C5B C4B 120.0(3) . . ?
C6B C5B HD 120.0 . . ?
C5B C6B HE 119.9 . . ?
C7B C6B C5B 120.2(3) . . ?
C7B C6B HE 119.9 . . ?
C2B C7B HF 119.9 . . ?
C6B C7B C2B 120.1(3) . . ?
C6B C7B HF 119.9 . . ?
O2B C8B C9B 111.5(3) . . ?
O3B C8B O2B 124.9(3) . . ?
O3B C8B C9B 123.6(3) . . ?
N1B C9B C8B 110.1(2) . . ?
N1B C9B HG 108.9 . . ?
N1B C9B C10B 110.0(2) . . ?
C8B C9B HG 108.9 . . ?
C8B C9B C10B 109.9(2) . . ?
C10B C9B HG 108.9 . . ?
C9B C10B HH 109.2 . . ?
C9B C10B HI 109.2 . . ?
HH C10B HI 107.9 . . ?
C11B C10B C9B 112.1(3) . . ?
C11B C10B HH 109.2 . . ?
C11B C10B HI 109.2 . . ?
C12B C11B C10B 120.3(3) . . ?
C16B C11B C10B 121.5(3) . . ?
C16B C11B C12B 118.2(3) . . ?
C11B C12B HJ 119.5 . . ?
C11B C12B C13B 121.0(4) . . ?
C13B C12B HJ 119.5 . . ?
C12B C13B HK 120.1 . . ?
C14B C13B C12B 119.9(4) . . ?
C14B C13B HK 120.1 . . ?
C13B C14B HL 120.2 . . ?
C15B C14B C13B 119.5(4) . . ?
C15B C14B HL 120.2 . . ?
C14B C15B HM 119.7 . . ?
C14B C15B C16B 120.6(4) . . ?
C16B C15B HM 119.7 . . ?
C11B C16B C15B 120.8(4) . . ?
C11B C16B HN 119.6 . . ?
C15B C16B HN 119.6 . . ?

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
O2A H2A O1A 0.87(5) 1.74(5) 2.598(3) 171(5) 2_656 yes
N1A H1A O3B 0.90(4) 2.07(4) 2.956(3) 167(3) . yes
O2B H O1B 0.85(5) 1.76(5) 2.601(3) 174(5) 2_647 yes
N1B HA O3A 0.83(4) 2.10(5) 2.921(4) 173(4) . 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
O1A C1A C2A C3A -26.9(5) . . . . ?
O1A C1A C2A C7A 155.4(3) . . . . ?
O2A C8A C9A N1A -155.9(3) . . . . ?
O2A C8A C9A C10A 81.0(3) . . . . ?
O3A C8A C9A N1A 26.2(4) . . . . ?
O3A C8A C9A C10A -96.9(4) . . . . ?
N1A C1A C2A C3A 151.1(3) . . . . ?
N1A C1A C2A C7A -26.7(4) . . . . ?
N1A C9A C10A C11A 69.2(12) . . . . ?
N1A C9A C10A C11C 89.6(4) . . . . ?
C1A N1A C9A C8A 61.1(4) . . . . ?
C1A N1A C9A C10A -177.3(3) . . . . ?
C1A C2A C3A C4A -176.0(3) . . . . ?
C1A C2A C7A C6A 175.7(3) . . . . ?
C2A C3A C4A C5A 1.2(6) . . . . ?
C3A C2A C7A C6A -2.0(5) . . . . ?
C3A C4A C5A C6A -4.0(6) . . . . ?
C3A C4A C5A C14A 179.2(3) . . . . ?
C4A C5A C6A C7A 3.8(5) . . . . ?
C4A C5A C14A F1A -8.3(4) . . . . ?
C4A C5A C14A F2A -129.1(4) . . . . ?
C4A C5A C14A F3A 111.2(4) . . . . ?
C4A C5A C14A F1B -34.4(5) . . . . ?
C4A C5A C14A F2B -147.4(5) . . . . ?
C4A C5A C14A F3B 91.7(6) . . . . ?
C4A C5A C14A F1C -55.6(5) . . . . ?
C4A C5A C14A F2C -160.2(5) . . . . ?
C4A C5A C14A F3C 58.0(6) . . . . ?
C5A C6A C7A C2A -0.7(5) . . . . ?
C6A C5A C14A F1A 174.8(4) . . . . ?
C6A C5A C14A F2A 54.0(4) . . . . ?
C6A C5A C14A F3A -65.7(4) . . . . ?
C6A C5A C14A F1B 148.7(5) . . . . ?
C6A C5A C14A F2B 35.7(5) . . . . ?
C6A C5A C14A F3B -85.2(5) . . . . ?
C6A C5A C14A F1C 127.5(5) . . . . ?
C6A C5A C14A F2C 22.9(5) . . . . ?
C6A C5A C14A F3C -118.9(6) . . . . ?
C7A C2A C3A C4A 1.8(5) . . . . ?
C8A C9A C10A C11A -169.3(11) . . . . ?
C8A C9A C10A C11C -148.9(3) . . . . ?
C9A N1A C1A O1A 6.0(4) . . . . ?
C9A N1A C1A C2A -172.0(3) . . . . ?
C9A C10A C11A C12A 174.2(16) . . . . ?
C9A C10A C11A C13A 52(2) . . . . ?
C9A C10A C11C C12C 175.6(3) . . . . ?
C9A C10A C11C C13C -61.0(5) . . . . ?
C14A C5A C6A C7A -179.3(3) . . . . ?
O1B C1B C2B C3B -154.2(3) . . . . ?
O1B C1B C2B C7B 27.1(4) . . . . ?
O2B C8B C9B N1B 158.4(3) . . . . ?
O2B C8B C9B C10B -80.3(3) . . . . ?
O3B C8B C9B N1B -22.3(4) . . . . ?
O3B C8B C9B C10B 99.0(3) . . . . ?
N1B C1B C2B C3B 26.6(4) . . . . ?
N1B C1B C2B C7B -152.0(3) . . . . ?
N1B C9B C10B C11B -64.2(3) . . . . ?
C1B N1B C9B C8B -63.8(4) . . . . ?
C1B N1B C9B C10B 175.0(3) . . . . ?
C1B C2B C3B C4B -177.6(3) . . . . ?
C1B C2B C7B C6B 177.6(3) . . . . ?
C2B C3B C4B C5B -1.0(5) . . . . ?
C3B C2B C7B C6B -1.0(5) . . . . ?
C3B C4B C5B C6B 1.1(6) . . . . ?
C4B C5B C6B C7B -1.1(6) . . . . ?
C5B C6B C7B C2B 1.1(6) . . . . ?
C7B C2B C3B C4B 1.0(5) . . . . ?
C8B C9B C10B C11B 174.4(3) . . . . ?
C9B N1B C1B O1B -4.2(4) . . . . ?
C9B N1B C1B C2B 174.9(3) . . . . ?
C9B C10B C11B C12B -85.1(4) . . . . ?
C9B C10B C11B C16B 94.5(4) . . . . ?
C10B C11B C12B C13B 178.5(4) . . . . ?
C10B C11B C16B C15B -178.2(4) . . . . ?
C11B C12B C13B C14B 0.1(7) . . . . ?
C12B C11B C16B C15B 1.4(6) . . . . ?
C12B C13B C14B C15B 0.7(8) . . . . ?
C13B C14B C15B C16B -0.4(8) . . . . ?
C14B C15B C16B C11B -0.7(7) . . . . ?
C16B C11B C12B C13B -1.1(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
####################################################################### 
# 
# 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_23kaw81
_database_code_depnum_ccdc_archive 'CCDC 2312810'
loop_
_audit_author_name
_audit_author_address
'Kraig Wheeler'
;Whitworth University
United States of America
;
_audit_update_record             
;
2023-12-18 deposited with the CCDC.	2024-02-12 downloaded from the CCDC.
;
_audit_creation_date             2023-12-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H16 F3 N O3'
_chemical_formula_sum            'C14 H16 F3 N O3'
_chemical_formula_weight         303.28
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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                   8.9660(4)
_cell_length_b                   17.0296(7)
_cell_length_c                   10.0714(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.371(2)
_cell_angle_gamma                90
_cell_volume                     1467.64(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9891
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.11
_cell_measurement_theta_min      5.17
_shelx_estimated_absorpt_T_max   0.965
_shelx_estimated_absorpt_T_min   0.694
_exptl_absorpt_coefficient_mu    1.049
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6253
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.375
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.034
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            22194
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.411
_diffrn_reflns_theta_min         5.169
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'κ-geometry four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'focusing mirror'
_diffrn_radiation_detector       'Bruker PHOTON II'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2317
_reflns_number_total             2684
_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       'SAINT+ V8.40B (Bruker AXS Inc., 2020)'
_computing_data_collection       'APEX5 Ver.2022.08-RC130 (Bruker-AXS, 2023)'
_computing_data_reduction        'SAINT+ Ve8.40B (Bruker-AXS, 2020)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2019/1)'
_computing_structure_solution    'XT (Sheldrick, 2018/2)'
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         2684
_refine_ls_number_restraints     44
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0600
_refine_ls_restrained_S_all      1.150
_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)+(0.0252P)²+1.3368P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1164
_refine_ls_wR_factor_ref         0.1227
_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron density map and refined using anisotropic displacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv of the connected C atoms (1.5xUeqiv for methyl groups). Those H atoms
 attached to nitrogen and oxygen were located in Fourier diff maps and assigned Uiso = 1.2xUeqiv for nitrogen (1.5 Ueqiv for oxygen).
The isopropyl and CF3 groups were modeled with two-part disorder with thier occupancy facgtors refined to 69:31 and 77:13, respectively. These fragments were restrained using a combination of SHELX RIGU, SADI, and ISOR commands.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O2-H2 = N1-H1
 0.85 with sigma of 0.02
 C10-C11 \\sim C10-C11A
 with sigma of 0.02
 C11-C12 \\sim C11A-C12A
 with sigma of 0.02
 C11-C13 \\sim C11A-C13A
 with sigma of 0.02
 C10-C12 \\sim C10-C12A
 with sigma of 0.02
 C10-C13 \\sim C10-C13A
 with sigma of 0.02
 C12-C13 \\sim C12A-C13A
 with sigma of 0.02
 F1-F2 \\sim F2-F3 \\sim F3-F1
 with sigma of 0.02
 F1-F1A \\sim F1A-F2 \\sim F2-F2A \\sim F2A-F3
 with sigma of 0.02
 F1-C14 \\sim F1A-C14
 with sigma of 0.02
 F2-C14 \\sim F2A-C14
 with sigma of 0.02
 F3-C14 \\sim F3A-C14
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F3A) \\sim Ueq, Uanis(F2A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.04
4. Rigid body (RIGU) restrains
 C11, C12, C13
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 C11A, C12A, C13A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 F1, F2, F3
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F1A, F2A, F3A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(H10C)=Sof(H10D)=Sof(C12A)=Sof(H12D)=Sof(H12E)=Sof(H12F)=Sof(C11A)=
 Sof(H11A)=Sof(C13A)=Sof(H13D)=Sof(H13E)=Sof(H13F)=1-FVAR(1)
 Sof(H10A)=Sof(H10B)=Sof(C11)=Sof(H11)=Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(H12C)=
 Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(H13C)=FVAR(1)
 Sof(F1A)=Sof(F3A)=Sof(F2A)=1-FVAR(2)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(2)
6.a Ternary CH refined with riding coordinates:
 C9(H9), C11(H11), C11A(H11A)
6.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C10(H10C,H10D)
6.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7)
6.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C12A(H12D,H12E,H12F), C13A(H13D,
 H13E,H13F)
;
_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
F1 F 0.0253(8) 0.4954(6) 0.3133(18) 0.069(3) Uani 0.65(6) 1 d D . P A 1
F2 F 0.1387(17) 0.5719(5) 0.4816(7) 0.069(2) Uani 0.65(6) 1 d D . P A 1
F3 F 0.2121(13) 0.5689(4) 0.2983(9) 0.053(2) Uani 0.65(6) 1 d D . P A 1
O1 O 0.6156(2) 0.25219(10) 0.73901(16) 0.0478(5) Uani 1 1 d . . . . .
O2 O 0.6958(2) 0.02311(11) 0.6087(2) 0.0635(6) Uani 1 1 d D . . . .
H2 H 0.626(3) -0.0141(17) 0.578(4) 0.095 Uiso 1 1 d D U . . .
O3 O 0.4991(2) 0.09413(10) 0.47549(19) 0.0498(5) Uani 1 1 d . . . . .
N1 N 0.6620(2) 0.23006(11) 0.53593(19) 0.0350(4) Uani 1 1 d D . . . .
H1 H 0.640(3) 0.2385(15) 0.4505(18) 0.042 Uiso 1 1 d D U . . .
C1 C 0.5946(3) 0.27016(13) 0.6163(2) 0.0354(5) Uani 1 1 d . . . . .
C2 C 0.4889(3) 0.33750(13) 0.5528(2) 0.0348(5) Uani 1 1 d . . . . .
C3 C 0.4000(3) 0.36973(14) 0.6308(2) 0.0391(5) Uani 1 1 d . . . . .
H3 H 0.410030 0.349951 0.721238 0.047 Uiso 1 1 calc R U . . .
C4 C 0.2968(3) 0.43045(15) 0.5778(3) 0.0438(6) Uani 1 1 d . . . . .
H4 H 0.235193 0.451743 0.631152 0.053 Uiso 1 1 calc R U . . .
C5 C 0.2835(3) 0.46009(14) 0.4466(3) 0.0411(6) Uani 1 1 d . . . . .
C6 C 0.3738(3) 0.42959(15) 0.3699(3) 0.0442(6) Uani 1 1 d . . . . .
H6 H 0.365825 0.450664 0.280662 0.053 Uiso 1 1 calc R U . . .
C7 C 0.4765(3) 0.36821(14) 0.4222(2) 0.0416(6) Uani 1 1 d . . . . .
H7 H 0.538271 0.347238 0.368640 0.050 Uiso 1 1 calc R U . . .
C8 C 0.6333(3) 0.08905(14) 0.5508(2) 0.0401(6) Uani 1 1 d . . . . .
C9 C 0.7466(3) 0.15767(13) 0.5854(2) 0.0377(5) Uani 1 1 d . . . . .
H9 H 0.791114 0.160990 0.688820 0.045 Uiso 1 1 calc R U . . .
C10 C 0.8805(3) 0.14282(15) 0.5240(3) 0.0448(6) Uani 1 1 d D . . . .
H10A H 0.934320 0.093808 0.564799 0.054 Uiso 0.690(11) 1 calc R U P B 1
H10B H 0.835770 0.134232 0.422637 0.054 Uiso 0.690(11) 1 calc R U P B 1
H10C H 0.849730 0.163204 0.427561 0.054 Uiso 0.310(11) 1 calc R U P B 2
H10D H 0.895335 0.085403 0.519218 0.054 Uiso 0.310(11) 1 calc R U P B 2
C11 C 1.0012(7) 0.2081(4) 0.5471(7) 0.0571(17) Uani 0.690(11) 1 d D . P B 1
H11 H 0.955977 0.253292 0.484637 0.069 Uiso 0.690(11) 1 calc R U P B 1
C12 C 1.0550(6) 0.2364(4) 0.6971(6) 0.0628(18) Uani 0.690(11) 1 d D . P B 1
H12A H 0.969086 0.264126 0.718382 0.094 Uiso 0.690(11) 1 calc R U P B 1
H12B H 1.143947 0.272057 0.710119 0.094 Uiso 0.690(11) 1 calc R U P B 1
H12C H 1.086477 0.191205 0.759457 0.094 Uiso 0.690(11) 1 calc R U P B 1
C13 C 1.1435(12) 0.1761(8) 0.5099(14) 0.116(6) Uani 0.690(11) 1 d D . P B 1
H13A H 1.196094 0.136446 0.578383 0.174 Uiso 0.690(11) 1 calc R U P B 1
H13B H 1.216151 0.219189 0.510340 0.174 Uiso 0.690(11) 1 calc R U P B 1
H13C H 1.109256 0.152273 0.417140 0.174 Uiso 0.690(11) 1 calc R U P B 1
C14 C 0.1666(3) 0.52307(17) 0.3875(3) 0.0527(7) Uani 1 1 d D . . . .
C12A C 1.157(2) 0.1586(13) 0.524(2) 0.067(6) Uani 0.310(11) 1 d D . P B 2
H12D H 1.110029 0.170184 0.425305 0.101 Uiso 0.310(11) 1 calc R U P B 2
H12E H 1.181849 0.102563 0.536326 0.101 Uiso 0.310(11) 1 calc R U P B 2
H12F H 1.252218 0.189559 0.560978 0.101 Uiso 0.310(11) 1 calc R U P B 2
C11A C 1.0383(13) 0.1801(8) 0.6049(16) 0.056(4) Uani 0.310(11) 1 d D . P B 2
H11A H 1.074743 0.160460 0.702858 0.067 Uiso 0.310(11) 1 calc R U P B 2
C13A C 1.0231(14) 0.2687(7) 0.601(2) 0.088(6) Uani 0.310(11) 1 d D . P B 2
H13D H 1.127251 0.292401 0.633755 0.132 Uiso 0.310(11) 1 calc R U P B 2
H13E H 0.960449 0.285304 0.660271 0.132 Uiso 0.310(11) 1 calc R U P B 2
H13F H 0.971924 0.285592 0.504723 0.132 Uiso 0.310(11) 1 calc R U P B 2
F1A F 0.0250(13) 0.4901(12) 0.338(3) 0.070(4) Uani 0.35(6) 1 d D . P A 2
F3A F 0.191(4) 0.5630(15) 0.281(3) 0.096(7) Uani 0.35(6) 1 d D U P A 2
F2A F 0.161(3) 0.5741(8) 0.4855(15) 0.076(5) Uani 0.35(6) 1 d D U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C14 1.349(7) . ?
F2 C14 1.339(7) . ?
F3 C14 1.342(6) . ?
O1 C1 1.232(3) . ?
O2 H2 0.879(19) . ?
O2 C8 1.311(3) . ?
O3 C8 1.219(3) . ?
N1 H1 0.835(17) . ?
N1 C1 1.334(3) . ?
N1 C9 1.455(3) . ?
C1 C2 1.503(3) . ?
C2 C3 1.388(3) . ?
C2 C7 1.390(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(3) . ?
C5 C6 1.378(4) . ?
C5 C14 1.494(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.389(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.519(3) . ?
C9 H9 1.0000 . ?
C9 C10 1.526(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 H10C 0.9900 . ?
C10 H10D 0.9900 . ?
C10 C11 1.520(6) . ?
C10 C11A 1.542(11) . ?
C11 H11 1.0000 . ?
C11 C12 1.520(9) . ?
C11 C13 1.533(10) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 F1A 1.340(11) . ?
C14 F3A 1.340(13) . ?
C14 F2A 1.328(11) . ?
C12A H12D 0.9800 . ?
C12A H12E 0.9800 . ?
C12A H12F 0.9800 . ?
C12A C11A 1.559(16) . ?
C11A H11A 1.0000 . ?
C11A C13A 1.514(18) . ?
C13A H13D 0.9800 . ?
C13A H13E 0.9800 . ?
C13A H13F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O2 H2 107(2) . . ?
C1 N1 H1 121.6(18) . . ?
C1 N1 C9 120.70(19) . . ?
C9 N1 H1 116.0(18) . . ?
O1 C1 N1 121.4(2) . . ?
O1 C1 C2 120.3(2) . . ?
N1 C1 C2 118.32(19) . . ?
C3 C2 C1 117.2(2) . . ?
C3 C2 C7 119.3(2) . . ?
C7 C2 C1 123.5(2) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.5(2) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.8(2) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C14 119.5(2) . . ?
C6 C5 C4 120.0(2) . . ?
C6 C5 C14 120.5(2) . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C7 120.4(2) . . ?
C7 C6 H6 119.8 . . ?
C2 C7 H7 120.0 . . ?
C6 C7 C2 119.9(2) . . ?
C6 C7 H7 120.0 . . ?
O2 C8 C9 112.9(2) . . ?
O3 C8 O2 123.3(2) . . ?
O3 C8 C9 123.8(2) . . ?
N1 C9 C8 109.19(19) . . ?
N1 C9 H9 108.3 . . ?
N1 C9 C10 113.2(2) . . ?
C8 C9 H9 108.3 . . ?
C8 C9 C10 109.45(19) . . ?
C10 C9 H9 108.3 . . ?
C9 C10 H10A 108.5 . . ?
C9 C10 H10B 108.5 . . ?
C9 C10 H10C 108.5 . . ?
C9 C10 H10D 108.5 . . ?
C9 C10 C11A 115.2(5) . . ?
H10A C10 H10B 107.5 . . ?
H10C C10 H10D 107.5 . . ?
C11 C10 C9 115.3(3) . . ?
C11 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
C11A C10 H10C 108.5 . . ?
C11A C10 H10D 108.5 . . ?
C10 C11 H11 109.3 . . ?
C10 C11 C12 112.6(5) . . ?
C10 C11 C13 108.0(6) . . ?
C12 C11 H11 109.3 . . ?
C12 C11 C13 108.4(6) . . ?
C13 C11 H11 109.3 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
F1 C14 C5 113.6(5) . . ?
F2 C14 F1 105.4(7) . . ?
F2 C14 F3 105.7(5) . . ?
F2 C14 C5 114.8(5) . . ?
F3 C14 F1 104.8(7) . . ?
F3 C14 C5 111.6(5) . . ?
F1A C14 C5 108.8(10) . . ?
F3A C14 C5 114.8(11) . . ?
F3A C14 F1A 106.2(15) . . ?
F2A C14 C5 110.7(9) . . ?
F2A C14 F1A 107.8(12) . . ?
F2A C14 F3A 108.3(13) . . ?
H12D C12A H12E 109.5 . . ?
H12D C12A H12F 109.5 . . ?
H12E C12A H12F 109.5 . . ?
C11A C12A H12D 109.5 . . ?
C11A C12A H12E 109.5 . . ?
C11A C12A H12F 109.5 . . ?
C10 C11A C12A 106.7(11) . . ?
C10 C11A H11A 111.2 . . ?
C12A C11A H11A 111.2 . . ?
C13A C11A C10 109.5(11) . . ?
C13A C11A C12A 106.7(12) . . ?
C13A C11A H11A 111.2 . . ?
C11A C13A H13D 109.5 . . ?
C11A C13A H13E 109.5 . . ?
C11A C13A H13F 109.5 . . ?
H13D C13A H13E 109.5 . . ?
H13D C13A H13F 109.5 . . ?
H13E C13A H13F 109.5 . . ?

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
O2 H2 O3 0.879(19) 1.745(19) 2.622(2) 175(4) 3_656 yes
N1 H1 O1 0.835(17) 2.082(17) 2.909(2) 170(2) 4_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
O1 C1 C2 C3 -9.4(3) . . . . ?
O1 C1 C2 C7 170.6(2) . . . . ?
O2 C8 C9 N1 -171.1(2) . . . . ?
O2 C8 C9 C10 64.4(3) . . . . ?
O3 C8 C9 N1 10.0(3) . . . . ?
O3 C8 C9 C10 -114.4(3) . . . . ?
N1 C1 C2 C3 169.4(2) . . . . ?
N1 C1 C2 C7 -10.5(3) . . . . ?
N1 C9 C10 C11 56.3(4) . . . . ?
N1 C9 C10 C11A 87.7(7) . . . . ?
C1 N1 C9 C8 88.0(2) . . . . ?
C1 N1 C9 C10 -149.8(2) . . . . ?
C1 C2 C3 C4 -178.2(2) . . . . ?
C1 C2 C7 C6 178.8(2) . . . . ?
C2 C3 C4 C5 -0.9(4) . . . . ?
C3 C2 C7 C6 -1.1(4) . . . . ?
C3 C4 C5 C6 -0.6(4) . . . . ?
C3 C4 C5 C14 177.2(2) . . . . ?
C4 C5 C6 C7 1.1(4) . . . . ?
C4 C5 C14 F1 -90.2(9) . . . . ?
C4 C5 C14 F2 31.3(7) . . . . ?
C4 C5 C14 F3 151.6(5) . . . . ?
C4 C5 C14 F1A -79.2(15) . . . . ?
C4 C5 C14 F3A 162.0(19) . . . . ?
C4 C5 C14 F2A 39.0(12) . . . . ?
C5 C6 C7 C2 -0.3(4) . . . . ?
C6 C5 C14 F1 87.5(9) . . . . ?
C6 C5 C14 F2 -150.9(7) . . . . ?
C6 C5 C14 F3 -30.7(5) . . . . ?
C6 C5 C14 F1A 98.6(15) . . . . ?
C6 C5 C14 F3A -20.2(19) . . . . ?
C6 C5 C14 F2A -143.2(12) . . . . ?
C7 C2 C3 C4 1.7(3) . . . . ?
C8 C9 C10 C11 178.4(4) . . . . ?
C8 C9 C10 C11A -150.3(7) . . . . ?
C9 N1 C1 O1 7.9(3) . . . . ?
C9 N1 C1 C2 -170.98(19) . . . . ?
C9 C10 C11 C12 47.5(7) . . . . ?
C9 C10 C11 C13 167.1(7) . . . . ?
C9 C10 C11A C12A -179.4(10) . . . . ?
C9 C10 C11A C13A -64.2(14) . . . . ?
C14 C5 C6 C7 -176.6(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
