# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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. 
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data_cu_ncsu_pn74_6_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2519170'
loop_
_audit_author_name
_audit_author_address
'Phattananawee Nalaoh'
;Department of Chemistry, the University of Tennessee
United States of America
;
_audit_update_record             
;
2025-12-28 deposited with the CCDC.	2026-03-26 downloaded from the CCDC.
;
_audit_creation_date             2024-05-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H21 N O'
_chemical_formula_sum            'C16 H21 N O'
_chemical_formula_weight         243.34
_chemical_absolute_configuration syn
_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                   9.5441(12)
_cell_length_b                   14.821(2)
_cell_length_c                   11.1946(15)
_cell_angle_alpha                90
_cell_angle_beta                 111.271(4)
_cell_angle_gamma                90
_cell_volume                     1475.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9736
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.42
_cell_measurement_theta_min      4.97
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.815
_exptl_absorpt_coefficient_mu    0.523
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_correction_T_min  0.6721
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0995 before and 0.0651 after correction.
The Ratio of minimum to maximum transmission is 0.8927.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.095
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             528
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 0.1590
-1.00 1.00 0.00 0.1960
0.00 -1.00 -1.00 0.0190
0.00 1.00 1.00 0.0300
0.00 -1.00 1.00 0.0820
0.00 1.00 -1.00 0.0850
1.00 0.00 -1.00 0.1260
1.00 -1.00 0.00 0.1580

_exptl_crystal_size_max          0.408
_exptl_crystal_size_mid          0.203
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            30070
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.545
_diffrn_reflns_theta_max         67.545
_diffrn_reflns_theta_min         4.238
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.908
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                5185
_reflns_number_total             5282
_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 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 2414 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.10(19)
_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     341
_refine_ls_number_reflns         5282
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0354
_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)+(0.0609P)²+0.2169P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.0933
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C24(H24), C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C31(H31A,H31B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C18(H18), C20(H20), C22(H22)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C16(H16A,H16B,
 H16C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C32(H32A,
 H32B,H32C)
2.e :
 C11(H11), C27(H27)
;
_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
C1 C 0.6466(2) 0.61775(14) 0.75744(19) 0.0233(4) Uani 1 1 d . . . . .
C2 C 0.7936(2) 0.63942(15) 0.8368(2) 0.0267(5) Uani 1 1 d . . . . .
H2 H 0.874418 0.601724 0.837524 0.032 Uiso 1 1 calc R U . . .
C3 C 0.8227(2) 0.71556(15) 0.9146(2) 0.0289(5) Uani 1 1 d . . . . .
C4 C 0.7026(3) 0.77021(15) 0.9124(2) 0.0282(5) Uani 1 1 d . . . . .
H4 H 0.721278 0.822090 0.965765 0.034 Uiso 1 1 calc R U . . .
C5 C 0.5569(2) 0.74984(15) 0.8336(2) 0.0251(4) Uani 1 1 d . . . . .
C6 C 0.5282(2) 0.67346(15) 0.7550(2) 0.0242(4) Uani 1 1 d . . . . .
H6 H 0.428327 0.659660 0.700153 0.029 Uiso 1 1 calc R U . . .
C7 C 0.5024(2) 0.48974(14) 0.62541(19) 0.0222(4) Uani 1 1 d . . . . .
C8 C 0.5228(2) 0.40162(14) 0.56368(19) 0.0222(4) Uani 1 1 d . . . . .
H8 H 0.631007 0.394464 0.574863 0.027 Uiso 1 1 calc R U . . .
C9 C 0.4758(2) 0.32309(15) 0.6330(2) 0.0274(5) Uani 1 1 d . . . . .
H9 H 0.367624 0.331978 0.620971 0.033 Uiso 1 1 calc R U . . .
C10 C 0.5647(3) 0.32968(18) 0.7711(2) 0.0383(6) Uani 1 1 d . . . . .
C11 C 0.6427(4) 0.3380(3) 0.8807(3) 0.0620(9) Uani 1 1 d . . . . .
H11 H 0.705122 0.344569 0.968316 0.074 Uiso 1 1 calc R U . . .
C12 C 0.9824(3) 0.73912(19) 0.9985(3) 0.0428(6) Uani 1 1 d . . . . .
H12A H 1.017094 0.790244 0.960979 0.064 Uiso 1 1 calc R U . . .
H12B H 1.047789 0.686979 1.004400 0.064 Uiso 1 1 calc R U . . .
H12C H 0.985915 0.755385 1.084350 0.064 Uiso 1 1 calc R U . . .
C13 C 0.4275(3) 0.81020(17) 0.8295(3) 0.0351(5) Uani 1 1 d . . . . .
H13A H 0.353777 0.775079 0.852184 0.053 Uiso 1 1 calc R U . . .
H13B H 0.379627 0.834852 0.742909 0.053 Uiso 1 1 calc R U . . .
H13C H 0.465270 0.859777 0.890714 0.053 Uiso 1 1 calc R U . . .
C14 C 0.4273(3) 0.40447(17) 0.4208(2) 0.0334(5) Uani 1 1 d . . . . .
H14A H 0.434151 0.346313 0.381609 0.050 Uiso 1 1 calc R U . . .
H14B H 0.464284 0.452422 0.379585 0.050 Uiso 1 1 calc R U . . .
H14C H 0.322331 0.416503 0.409543 0.050 Uiso 1 1 calc R U . . .
C15 C 0.4916(3) 0.22843(16) 0.5815(3) 0.0367(5) Uani 1 1 d . . . . .
H15A H 0.455641 0.182916 0.628428 0.044 Uiso 1 1 calc R U . . .
H15B H 0.425765 0.225043 0.489944 0.044 Uiso 1 1 calc R U . . .
C16 C 0.6507(3) 0.20443(17) 0.5937(3) 0.0403(6) Uani 1 1 d . . . . .
H16A H 0.654434 0.141002 0.570348 0.060 Uiso 1 1 calc R U . . .
H16B H 0.718874 0.213926 0.682443 0.060 Uiso 1 1 calc R U . . .
H16C H 0.681533 0.242848 0.536394 0.060 Uiso 1 1 calc R U . . .
C17 C 0.1936(2) 0.49319(13) 0.85762(19) 0.0210(4) Uani 1 1 d . . . . .
C18 C 0.3392(2) 0.52744(14) 0.9156(2) 0.0240(4) Uani 1 1 d . . . . .
H18 H 0.402026 0.533305 0.866873 0.029 Uiso 1 1 calc R U . . .
C19 C 0.3927(2) 0.55293(15) 1.0434(2) 0.0272(5) Uani 1 1 d . . . . .
C20 C 0.2983(3) 0.54300(15) 1.1130(2) 0.0296(5) Uani 1 1 d . . . . .
H20 H 0.333208 0.561040 1.200311 0.036 Uiso 1 1 calc R U . . .
C21 C 0.1548(3) 0.50745(15) 1.0576(2) 0.0287(5) Uani 1 1 d . . . . .
C22 C 0.1020(2) 0.48162(14) 0.9289(2) 0.0235(4) Uani 1 1 d . . . . .
H22 H 0.004410 0.456370 0.890358 0.028 Uiso 1 1 calc R U . . .
C23 C 0.0107(2) 0.45220(13) 0.64191(18) 0.0202(4) Uani 1 1 d . . . . .
C24 C 0.0046(2) 0.42720(13) 0.5080(2) 0.0215(4) Uani 1 1 d . . . . .
H24 H 0.104687 0.439757 0.501736 0.026 Uiso 1 1 calc R U . . .
C25 C -0.0300(2) 0.32453(13) 0.4868(2) 0.0213(4) Uani 1 1 d . . . . .
H25 H -0.138180 0.315822 0.474875 0.026 Uiso 1 1 calc R U . . .
C26 C 0.0599(2) 0.27218(15) 0.6001(2) 0.0266(4) Uani 1 1 d . . . . .
C27 C 0.1333(3) 0.23223(17) 0.6944(2) 0.0363(5) Uani 1 1 d . . . . .
H27 H 0.191860 0.200380 0.769663 0.044 Uiso 1 1 calc R U . . .
C28 C 0.5487(3) 0.59138(19) 1.1046(2) 0.0379(6) Uani 1 1 d . . . . .
H28A H 0.601425 0.560217 1.185722 0.057 Uiso 1 1 calc R U . . .
H28B H 0.542005 0.655905 1.120873 0.057 Uiso 1 1 calc R U . . .
H28C H 0.604072 0.583023 1.046825 0.057 Uiso 1 1 calc R U . . .
C29 C 0.0557(3) 0.4952(2) 1.1353(2) 0.0409(6) Uani 1 1 d . . . . .
H29A H -0.048818 0.508603 1.081580 0.061 Uiso 1 1 calc R U . . .
H29B H 0.088496 0.536197 1.208906 0.061 Uiso 1 1 calc R U . . .
H29C H 0.062963 0.432699 1.165662 0.061 Uiso 1 1 calc R U . . .
C30 C -0.1152(3) 0.48409(15) 0.4083(2) 0.0300(5) Uani 1 1 d . . . . .
H30A H -0.121368 0.466446 0.322117 0.045 Uiso 1 1 calc R U . . .
H30B H -0.088167 0.548054 0.422206 0.045 Uiso 1 1 calc R U . . .
H30C H -0.212776 0.474223 0.416550 0.045 Uiso 1 1 calc R U . . .
C31 C -0.0089(2) 0.28896(15) 0.3655(2) 0.0270(5) Uani 1 1 d . . . . .
H31A H -0.071952 0.324988 0.290940 0.032 Uiso 1 1 calc R U . . .
H31B H 0.097406 0.297344 0.374527 0.032 Uiso 1 1 calc R U . . .
C32 C -0.0501(3) 0.18967(15) 0.3398(2) 0.0319(5) Uani 1 1 d . . . . .
H32A H -0.051602 0.173388 0.254529 0.048 Uiso 1 1 calc R U . . .
H32B H -0.149681 0.179158 0.343802 0.048 Uiso 1 1 calc R U . . .
H32C H 0.024504 0.152595 0.404648 0.048 Uiso 1 1 calc R U . . .
N1 N 0.62876(19) 0.53845(12) 0.68209(17) 0.0233(4) Uani 1 1 d . . . . .
N2 N 0.14947(18) 0.47105(11) 0.72593(16) 0.0202(4) Uani 1 1 d . . . . .
O1 O 0.37642(15) 0.51317(10) 0.62200(14) 0.0274(3) Uani 1 1 d . . . . .
O2 O -0.10429(15) 0.45282(11) 0.66777(14) 0.0269(3) Uani 1 1 d . . . . .
H2A H 0.221(3) 0.4739(18) 0.695(2) 0.027(6) Uiso 1 1 d . . . . .
H1 H 0.718(3) 0.5138(19) 0.680(2) 0.028(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.398(3) . ?
C1 C6 1.392(3) . ?
C1 N1 1.420(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.391(3) . ?
C3 C4 1.396(3) . ?
C3 C12 1.513(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(3) . ?
C5 C6 1.399(3) . ?
C5 C13 1.512(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.523(3) . ?
C7 N1 1.350(3) . ?
C7 O1 1.239(2) . ?
C8 H8 1.0000 . ?
C8 C9 1.552(3) . ?
C8 C14 1.527(3) . ?
C9 H9 1.0000 . ?
C9 C10 1.473(4) . ?
C9 C15 1.545(3) . ?
C10 C11 1.188(4) . ?
C11 H11 0.9500 . ?
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 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.516(4) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.398(3) . ?
C17 C22 1.392(3) . ?
C17 N2 1.417(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.386(3) . ?
C19 C20 1.396(3) . ?
C19 C28 1.507(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.386(3) . ?
C21 C22 1.396(3) . ?
C21 C29 1.510(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.525(3) . ?
C23 N2 1.347(2) . ?
C23 O2 1.232(2) . ?
C24 H24 1.0000 . ?
C24 C25 1.557(3) . ?
C24 C30 1.529(3) . ?
C25 H25 1.0000 . ?
C25 C26 1.469(3) . ?
C25 C31 1.536(3) . ?
C26 C27 1.192(3) . ?
C27 H27 0.9500 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.523(3) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
N1 H1 0.93(3) . ?
N2 H2A 0.86(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 116.36(18) . . ?
C6 C1 C2 119.77(19) . . ?
C6 C1 N1 123.86(19) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.7(2) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 C4 118.9(2) . . ?
C2 C3 C12 120.2(2) . . ?
C4 C3 C12 120.9(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.9(2) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 120.0(2) . . ?
C4 C5 C13 120.8(2) . . ?
C6 C5 C13 119.2(2) . . ?
C1 C6 C5 119.69(19) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
N1 C7 C8 115.61(17) . . ?
O1 C7 C8 120.60(17) . . ?
O1 C7 N1 123.79(19) . . ?
C7 C8 H8 109.3 . . ?
C7 C8 C9 107.97(16) . . ?
C7 C8 C14 109.01(17) . . ?
C9 C8 H8 109.3 . . ?
C14 C8 H8 109.3 . . ?
C14 C8 C9 111.91(18) . . ?
C8 C9 H9 107.8 . . ?
C10 C9 C8 108.31(19) . . ?
C10 C9 H9 107.8 . . ?
C10 C9 C15 110.8(2) . . ?
C15 C9 C8 114.16(18) . . ?
C15 C9 H9 107.8 . . ?
C11 C10 C9 176.0(3) . . ?
C10 C11 H11 180.0 . . ?
C3 C12 H12A 109.5 . . ?
C3 C12 H12B 109.5 . . ?
C3 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C5 C13 H13A 109.5 . . ?
C5 C13 H13B 109.5 . . ?
C5 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C8 C14 H14A 109.5 . . ?
C8 C14 H14B 109.5 . . ?
C8 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C9 C15 H15A 108.7 . . ?
C9 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
C16 C15 C9 114.2(2) . . ?
C16 C15 H15A 108.7 . . ?
C16 C15 H15B 108.7 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 N2 115.94(18) . . ?
C22 C17 C18 120.24(19) . . ?
C22 C17 N2 123.81(18) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.7(2) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 C20 118.4(2) . . ?
C18 C19 C28 120.3(2) . . ?
C20 C19 C28 121.2(2) . . ?
C19 C20 H20 119.2 . . ?
C21 C20 C19 121.6(2) . . ?
C21 C20 H20 119.2 . . ?
C20 C21 C22 119.6(2) . . ?
C20 C21 C29 120.8(2) . . ?
C22 C21 C29 119.6(2) . . ?
C17 C22 C21 119.42(19) . . ?
C17 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
N2 C23 C24 114.45(17) . . ?
O2 C23 C24 120.89(17) . . ?
O2 C23 N2 124.65(18) . . ?
C23 C24 H24 109.1 . . ?
C23 C24 C25 108.51(16) . . ?
C23 C24 C30 109.59(17) . . ?
C25 C24 H24 109.1 . . ?
C30 C24 H24 109.1 . . ?
C30 C24 C25 111.50(16) . . ?
C24 C25 H25 107.4 . . ?
C26 C25 C24 111.06(16) . . ?
C26 C25 H25 107.4 . . ?
C26 C25 C31 111.01(17) . . ?
C31 C25 C24 112.42(17) . . ?
C31 C25 H25 107.4 . . ?
C27 C26 C25 177.8(2) . . ?
C26 C27 H27 180.0 . . ?
C19 C28 H28A 109.5 . . ?
C19 C28 H28B 109.5 . . ?
C19 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C21 C29 H29A 109.5 . . ?
C21 C29 H29B 109.5 . . ?
C21 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C24 C30 H30A 109.5 . . ?
C24 C30 H30B 109.5 . . ?
C24 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C25 C31 H31A 109.0 . . ?
C25 C31 H31B 109.0 . . ?
H31A C31 H31B 107.8 . . ?
C32 C31 C25 112.99(19) . . ?
C32 C31 H31A 109.0 . . ?
C32 C31 H31B 109.0 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C1 N1 H1 115.1(17) . . ?
C7 N1 C1 128.01(17) . . ?
C7 N1 H1 116.5(17) . . ?
C17 N2 H2A 114.9(17) . . ?
C23 N2 C17 128.36(17) . . ?
C23 N2 H2A 116.6(17) . . ?

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
C1 C2 C3 C4 0.0(3) . . . . ?
C1 C2 C3 C12 -179.0(2) . . . . ?
C2 C1 C6 C5 -1.1(3) . . . . ?
C2 C1 N1 C7 160.9(2) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C3 C4 C5 C13 -178.8(2) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C6 C1 C2 C3 0.8(3) . . . . ?
C6 C1 N1 C7 -19.7(3) . . . . ?
C7 C8 C9 C10 -55.6(2) . . . . ?
C7 C8 C9 C15 -179.50(18) . . . . ?
C8 C7 N1 C1 -173.14(18) . . . . ?
C8 C9 C15 C16 60.7(3) . . . . ?
C10 C9 C15 C16 -61.9(3) . . . . ?
C12 C3 C4 C5 178.5(2) . . . . ?
C13 C5 C6 C1 179.6(2) . . . . ?
C14 C8 C9 C10 -175.54(19) . . . . ?
C14 C8 C9 C15 60.5(2) . . . . ?
C17 C18 C19 C20 0.4(3) . . . . ?
C17 C18 C19 C28 -178.9(2) . . . . ?
C18 C17 C22 C21 2.2(3) . . . . ?
C18 C17 N2 C23 -167.38(19) . . . . ?
C18 C19 C20 C21 0.9(3) . . . . ?
C19 C20 C21 C22 -0.7(3) . . . . ?
C19 C20 C21 C29 178.5(2) . . . . ?
C20 C21 C22 C17 -0.9(3) . . . . ?
C22 C17 C18 C19 -2.0(3) . . . . ?
C22 C17 N2 C23 13.4(3) . . . . ?
C23 C24 C25 C26 -44.0(2) . . . . ?
C23 C24 C25 C31 -169.07(17) . . . . ?
C24 C23 N2 C17 -177.55(18) . . . . ?
C24 C25 C31 C32 -177.06(17) . . . . ?
C26 C25 C31 C32 57.9(2) . . . . ?
C28 C19 C20 C21 -179.8(2) . . . . ?
C29 C21 C22 C17 179.9(2) . . . . ?
C30 C24 C25 C26 -164.79(18) . . . . ?
C30 C24 C25 C31 70.1(2) . . . . ?
N1 C1 C2 C3 -179.8(2) . . . . ?
N1 C1 C6 C5 179.48(19) . . . . ?
N1 C7 C8 C9 118.1(2) . . . . ?
N1 C7 C8 C14 -120.2(2) . . . . ?
N2 C17 C18 C19 178.73(19) . . . . ?
N2 C17 C22 C21 -178.57(18) . . . . ?
N2 C23 C24 C25 108.82(19) . . . . ?
N2 C23 C24 C30 -129.22(19) . . . . ?
O1 C7 C8 C9 -62.0(2) . . . . ?
O1 C7 C8 C14 59.8(2) . . . . ?
O1 C7 N1 C1 6.9(3) . . . . ?
O2 C23 C24 C25 -70.0(2) . . . . ?
O2 C23 C24 C30 51.9(2) . . . . ?
O2 C23 N2 C17 1.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_compound_source        synthetic
####################################################################### 
# 
# 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_ncsu_pn89_a
_database_code_depnum_ccdc_archive 'CCDC 2519172'
loop_
_audit_author_name
_audit_author_address
'Phattananawee Nalaoh'
;Department of Chemistry, the University of Tennessee
United States of America
;
_audit_update_record             
;
2025-12-28 deposited with the CCDC.	2026-03-26 downloaded from the CCDC.
;
_audit_creation_date             2025-07-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7311)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H21 N O4 S'
_chemical_formula_sum            'C15 H21 N O4 S'
_chemical_formula_weight         311.39
_chemical_absolute_configuration syn
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   12.0469(13)
_cell_length_b                   7.6540(10)
_cell_length_c                   17.8313(19)
_cell_angle_alpha                90
_cell_angle_beta                 103.462(6)
_cell_angle_gamma                90
_cell_volume                     1599.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4060
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      68.17
_cell_measurement_theta_min      6.32
_shelx_estimated_absorpt_T_max   0.951
_shelx_estimated_absorpt_T_min   0.363
_exptl_absorpt_coefficient_mu    1.932
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1042 before and 0.0521 after correction.
The Ratio of minimum to maximum transmission is 0.8085.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.659
_exptl_crystal_size_mid          0.206
_exptl_crystal_size_min          0.026
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_unetI/netI     0.0715
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9432
_diffrn_reflns_point_group_measured_fraction_full 0.904
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.345
_diffrn_reflns_theta_min         5.596
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.678
_reflns_Friedel_fraction_full    0.797
_reflns_Friedel_fraction_max     0.790
_reflns_number_gt                4766
_reflns_number_total             5285
_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 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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, 2015)'
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details 
;
 Flack x determined using 1752 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.006(19)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     407
_refine_ls_number_reflns         5285
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0504
_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)+(0.0614P)²+0.4568P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1170
_refine_ls_wR_factor_ref         0.1287
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C10(H10A,H10B), C13(H13A,H13B), C14(H14A,H14B), C22(H22A,H22B),
 C25(H25A,H25B), C27(H27A,H27B), C28(H28A,H28B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C17(H17), C18(H18), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C26(H26A,H26B,H26C), C30(H30A,H30B,
 H30C)
;
_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
C1 C 0.5801(3) 0.3352(6) 0.1041(2) 0.0299(8) Uani 1 1 d . . . . .
C2 C 0.6749(3) 0.2351(6) 0.1015(3) 0.0319(8) Uani 1 1 d . . . . .
H2 H 0.712379 0.168942 0.145155 0.038 Uiso 1 1 calc R U . . .
C3 C 0.7144(3) 0.2324(6) 0.0347(3) 0.0353(9) Uani 1 1 d . . . . .
H3 H 0.780386 0.165639 0.033406 0.042 Uiso 1 1 calc R U . . .
C4 C 0.6598(4) 0.3254(6) -0.0311(2) 0.0379(9) Uani 1 1 d . . . . .
C5 C 0.5644(4) 0.4250(6) -0.0269(2) 0.0380(9) Uani 1 1 d . . . . .
H5 H 0.525553 0.488920 -0.070836 0.046 Uiso 1 1 calc R U . . .
C6 C 0.5252(3) 0.4326(6) 0.0404(3) 0.0339(8) Uani 1 1 d . . . . .
H6 H 0.461497 0.503633 0.042810 0.041 Uiso 1 1 calc R U . . .
C7 C 0.6146(4) 0.6535(7) 0.2417(3) 0.0382(9) Uani 1 1 d . . . . .
H7A H 0.560541 0.709715 0.268417 0.046 Uiso 1 1 calc R U . . .
H7B H 0.593012 0.684681 0.186347 0.046 Uiso 1 1 calc R U . . .
C8 C 0.7372(4) 0.7081(6) 0.2778(3) 0.0355(9) Uani 1 1 d . . . . .
C9 C 0.7823(4) 0.5623(6) 0.3362(2) 0.0333(9) Uani 1 1 d . . . . .
C10 C 0.7311(4) 0.4003(6) 0.2915(3) 0.0348(9) Uani 1 1 d . . . . .
H10A H 0.775562 0.364455 0.253876 0.042 Uiso 1 1 calc R U . . .
H10B H 0.727258 0.301450 0.326619 0.042 Uiso 1 1 calc R U . . .
C11 C 0.7009(5) 0.3165(8) -0.1038(3) 0.0494(12) Uani 1 1 d . . . . .
H11A H 0.779871 0.274354 -0.092158 0.074 Uiso 1 1 calc R U . . .
H11B H 0.697433 0.433168 -0.126892 0.074 Uiso 1 1 calc R U . . .
H11C H 0.652403 0.236273 -0.140015 0.074 Uiso 1 1 calc R U . . .
C12 C 0.7478(5) 0.8913(7) 0.3105(3) 0.0475(12) Uani 1 1 d . . . . .
H12A H 0.710091 0.973761 0.270591 0.071 Uiso 1 1 calc R U . . .
H12B H 0.828637 0.922128 0.327925 0.071 Uiso 1 1 calc R U . . .
H12C H 0.711402 0.896851 0.354249 0.071 Uiso 1 1 calc R U . . .
C13 C 0.9110(3) 0.5648(6) 0.3632(2) 0.0340(8) Uani 1 1 d . . . . .
H13A H 0.934539 0.679047 0.387804 0.041 Uiso 1 1 calc R U . . .
H13B H 0.944220 0.555173 0.317522 0.041 Uiso 1 1 calc R U . . .
C14 C 0.9610(4) 0.4207(7) 0.4198(3) 0.0401(9) Uani 1 1 d . . . . .
H14A H 0.917850 0.413707 0.460624 0.048 Uiso 1 1 calc R U . . .
H14B H 0.953216 0.307129 0.392433 0.048 Uiso 1 1 calc R U . . .
C15 C 1.0848(4) 0.4543(6) 0.4559(2) 0.0356(9) Uani 1 1 d . . . . .
C16 C 0.9245(3) 0.6660(6) 0.8757(2) 0.0286(7) Uani 1 1 d . . . . .
C17 C 0.9761(3) 0.5602(6) 0.9374(3) 0.0340(8) Uani 1 1 d . . . . .
H17 H 1.036809 0.484509 0.933152 0.041 Uiso 1 1 calc R U . . .
C18 C 0.9384(4) 0.5655(6) 1.0054(3) 0.0366(9) Uani 1 1 d . . . . .
H18 H 0.974168 0.493295 1.047442 0.044 Uiso 1 1 calc R U . . .
C19 C 0.8498(3) 0.6739(6) 1.0131(2) 0.0356(9) Uani 1 1 d . . . . .
C20 C 0.7975(3) 0.7776(6) 0.9501(3) 0.0345(9) Uani 1 1 d . . . . .
H20 H 0.735371 0.850559 0.954191 0.041 Uiso 1 1 calc R U . . .
C21 C 0.8339(3) 0.7765(6) 0.8820(2) 0.0313(8) Uani 1 1 d . . . . .
H21 H 0.798211 0.849332 0.840173 0.038 Uiso 1 1 calc R U . . .
C22 C 0.7693(4) 0.6051(6) 0.6887(3) 0.0378(9) Uani 1 1 d . . . . .
H22A H 0.771361 0.662566 0.639301 0.045 Uiso 1 1 calc R U . . .
H22B H 0.740065 0.689061 0.721682 0.045 Uiso 1 1 calc R U . . .
C23 C 0.6962(4) 0.4404(6) 0.6751(2) 0.0343(9) Uani 1 1 d . . . . .
C24 C 0.7820(4) 0.2938(6) 0.6758(3) 0.0375(9) Uani 1 1 d . . . . .
C25 C 0.8834(3) 0.3490(6) 0.7406(3) 0.0365(9) Uani 1 1 d . . . . .
H25A H 0.870348 0.320229 0.791983 0.044 Uiso 1 1 calc R U . . .
H25B H 0.955207 0.293728 0.734849 0.044 Uiso 1 1 calc R U . . .
C26 C 0.8110(4) 0.6808(8) 1.0877(3) 0.0479(12) Uani 1 1 d . . . . .
H26A H 0.853757 0.594732 1.123832 0.072 Uiso 1 1 calc R U . . .
H26B H 0.729285 0.654149 1.077501 0.072 Uiso 1 1 calc R U . . .
H26C H 0.824796 0.797931 1.110059 0.072 Uiso 1 1 calc R U . . .
C27 C 0.6000(4) 0.4453(7) 0.6022(3) 0.0400(9) Uani 1 1 d . . . . .
H27A H 0.633772 0.457789 0.556857 0.048 Uiso 1 1 calc R U . . .
H27B H 0.558617 0.332567 0.597104 0.048 Uiso 1 1 calc R U . . .
C28 C 0.5151(4) 0.5928(6) 0.6013(3) 0.0389(9) Uani 1 1 d . . . . .
H28A H 0.506907 0.612973 0.654599 0.047 Uiso 1 1 calc R U . . .
H28B H 0.546049 0.701179 0.583647 0.047 Uiso 1 1 calc R U . . .
C29 C 0.3990(4) 0.5573(7) 0.5501(2) 0.0357(9) Uani 1 1 d . . . . .
C30 C 0.7388(5) 0.1113(7) 0.6872(3) 0.0469(11) Uani 1 1 d . . . . .
H30A H 0.703269 0.111519 0.731346 0.070 Uiso 1 1 calc R U . . .
H30B H 0.802980 0.029144 0.696903 0.070 Uiso 1 1 calc R U . . .
H30C H 0.682471 0.075687 0.640716 0.070 Uiso 1 1 calc R U . . .
N1 N 0.6156(3) 0.4614(5) 0.2522(2) 0.0347(8) Uani 1 1 d . . . . .
N2 N 0.8849(3) 0.5389(5) 0.7284(2) 0.0347(7) Uani 1 1 d . . . . .
O1 O 0.4216(2) 0.4293(5) 0.17231(19) 0.0425(7) Uani 1 1 d . . . . .
O2 O 0.5379(2) 0.1661(5) 0.21947(17) 0.0389(7) Uani 1 1 d . . . . .
O3 O 1.1208(3) 0.6024(5) 0.4736(2) 0.0460(8) Uani 1 1 d . . . . .
O4 O 1.1505(3) 0.3166(5) 0.46717(19) 0.0437(8) Uani 1 1 d . . . . .
O5 O 0.9630(3) 0.8329(5) 0.75853(18) 0.0430(7) Uani 1 1 d . . . . .
O6 O 1.0799(2) 0.5716(5) 0.80661(19) 0.0442(8) Uani 1 1 d . . . . .
O7 O 0.3701(3) 0.4181(5) 0.51846(19) 0.0462(8) Uani 1 1 d . . . . .
O8 O 0.3295(3) 0.6914(4) 0.54540(19) 0.0410(7) Uani 1 1 d . . . . .
S1 S 0.52971(7) 0.34156(13) 0.18954(5) 0.0318(2) Uani 1 1 d . . . . .
S2 S 0.97197(7) 0.66008(13) 0.78965(6) 0.0329(3) Uani 1 1 d . . . . .
H9 H 0.751(4) 0.581(7) 0.376(3) 0.026(11) Uiso 1 1 d . . . . .
H8 H 0.786(5) 0.697(8) 0.241(3) 0.038(13) Uiso 1 1 d . . . . .
H24 H 0.811(4) 0.307(7) 0.630(3) 0.030(11) Uiso 1 1 d . . . . .
H23 H 0.661(5) 0.419(8) 0.718(3) 0.043(14) Uiso 1 1 d . . . . .
H8A H 0.260(6) 0.671(10) 0.524(4) 0.048(15) Uiso 1 1 d . . . . .
H4 H 1.223(7) 0.348(12) 0.487(4) 0.061(18) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.385(6) . ?
C1 C6 1.392(6) . ?
C1 S1 1.767(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.399(7) . ?
C4 C5 1.396(7) . ?
C4 C11 1.492(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(7) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.526(6) . ?
C7 N1 1.481(6) . ?
C8 C9 1.537(6) . ?
C8 C12 1.513(7) . ?
C8 H8 0.99(6) . ?
C9 C10 1.524(6) . ?
C9 C13 1.513(6) . ?
C9 H9 0.89(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 N1 1.480(5) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.521(6) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.503(6) . ?
C15 O3 1.228(6) . ?
C15 O4 1.306(6) . ?
C16 C17 1.391(6) . ?
C16 C21 1.406(6) . ?
C16 S2 1.759(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.391(6) . ?
C18 H18 0.9500 . ?
C18 C19 1.383(7) . ?
C19 C20 1.400(7) . ?
C19 C26 1.509(6) . ?
C20 H20 0.9500 . ?
C20 C21 1.383(6) . ?
C21 H21 0.9500 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.524(7) . ?
C22 N2 1.495(6) . ?
C23 C24 1.524(6) . ?
C23 C27 1.527(6) . ?
C23 H23 0.98(6) . ?
C24 C25 1.533(6) . ?
C24 C30 1.520(7) . ?
C24 H24 0.96(5) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 N2 1.470(6) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.521(7) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C29 1.507(6) . ?
C29 O7 1.217(6) . ?
C29 O8 1.315(6) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
N1 S1 1.620(4) . ?
N2 S2 1.618(4) . ?
O1 S1 1.433(3) . ?
O2 S1 1.440(4) . ?
O4 H4 0.90(8) . ?
O5 S2 1.429(4) . ?
O6 S2 1.434(4) . ?
O8 H8A 0.85(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.5(4) . . ?
C2 C1 S1 119.8(3) . . ?
C6 C1 S1 119.7(3) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.3(4) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 119.1 . . ?
C2 C3 C4 121.8(4) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 C11 121.3(4) . . ?
C5 C4 C3 117.7(4) . . ?
C5 C4 C11 121.1(4) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.3(4) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 H6 120.3 . . ?
C5 C6 C1 119.4(4) . . ?
C5 C6 H6 120.3 . . ?
H7A C7 H7B 109.0 . . ?
C8 C7 H7A 111.0 . . ?
C8 C7 H7B 111.0 . . ?
N1 C7 H7A 111.0 . . ?
N1 C7 H7B 111.0 . . ?
N1 C7 C8 103.9(3) . . ?
C7 C8 C9 104.0(4) . . ?
C7 C8 H8 111(3) . . ?
C9 C8 H8 102(3) . . ?
C12 C8 C7 113.8(4) . . ?
C12 C8 C9 115.3(4) . . ?
C12 C8 H8 109(3) . . ?
C8 C9 H9 106(3) . . ?
C10 C9 C8 101.5(3) . . ?
C10 C9 H9 110(3) . . ?
C13 C9 C8 112.4(4) . . ?
C13 C9 C10 115.9(4) . . ?
C13 C9 H9 110(3) . . ?
C9 C10 H10A 111.3 . . ?
C9 C10 H10B 111.3 . . ?
H10A C10 H10B 109.2 . . ?
N1 C10 C9 102.2(4) . . ?
N1 C10 H10A 111.3 . . ?
N1 C10 H10B 111.3 . . ?
C4 C11 H11A 109.5 . . ?
C4 C11 H11B 109.5 . . ?
C4 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 H13A 108.6 . . ?
C9 C13 H13B 108.6 . . ?
C9 C13 C14 114.8(4) . . ?
H13A C13 H13B 107.5 . . ?
C14 C13 H13A 108.6 . . ?
C14 C13 H13B 108.6 . . ?
C13 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C15 C14 C13 111.1(4) . . ?
C15 C14 H14A 109.4 . . ?
C15 C14 H14B 109.4 . . ?
O3 C15 C14 121.6(4) . . ?
O3 C15 O4 122.7(4) . . ?
O4 C15 C14 115.7(4) . . ?
C17 C16 C21 120.0(4) . . ?
C17 C16 S2 119.9(3) . . ?
C21 C16 S2 120.1(3) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.7(4) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 119.3 . . ?
C19 C18 C17 121.3(4) . . ?
C19 C18 H18 119.3 . . ?
C18 C19 C20 118.3(4) . . ?
C18 C19 C26 120.8(4) . . ?
C20 C19 C26 120.9(4) . . ?
C19 C20 H20 119.2 . . ?
C21 C20 C19 121.7(4) . . ?
C21 C20 H20 119.2 . . ?
C16 C21 H21 120.5 . . ?
C20 C21 C16 118.9(4) . . ?
C20 C21 H21 120.5 . . ?
H22A C22 H22B 109.0 . . ?
C23 C22 H22A 111.0 . . ?
C23 C22 H22B 111.0 . . ?
N2 C22 H22A 111.0 . . ?
N2 C22 H22B 111.0 . . ?
N2 C22 C23 103.6(4) . . ?
C22 C23 C27 114.3(4) . . ?
C22 C23 H23 111(4) . . ?
C24 C23 C22 104.0(3) . . ?
C24 C23 C27 113.8(4) . . ?
C24 C23 H23 107(4) . . ?
C27 C23 H23 107(3) . . ?
C23 C24 C25 102.9(3) . . ?
C23 C24 H24 107(3) . . ?
C25 C24 H24 103(3) . . ?
C30 C24 C23 115.2(4) . . ?
C30 C24 C25 112.9(4) . . ?
C30 C24 H24 114(3) . . ?
C24 C25 H25A 111.5 . . ?
C24 C25 H25B 111.5 . . ?
H25A C25 H25B 109.3 . . ?
N2 C25 C24 101.3(4) . . ?
N2 C25 H25A 111.5 . . ?
N2 C25 H25B 111.5 . . ?
C19 C26 H26A 109.5 . . ?
C19 C26 H26B 109.5 . . ?
C19 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C23 C27 H27A 108.8 . . ?
C23 C27 H27B 108.8 . . ?
H27A C27 H27B 107.7 . . ?
C28 C27 C23 113.7(4) . . ?
C28 C27 H27A 108.8 . . ?
C28 C27 H27B 108.8 . . ?
C27 C28 H28A 108.9 . . ?
C27 C28 H28B 108.9 . . ?
H28A C28 H28B 107.7 . . ?
C29 C28 C27 113.5(4) . . ?
C29 C28 H28A 108.9 . . ?
C29 C28 H28B 108.9 . . ?
O7 C29 C28 124.3(4) . . ?
O7 C29 O8 123.0(4) . . ?
O8 C29 C28 112.6(4) . . ?
C24 C30 H30A 109.5 . . ?
C24 C30 H30B 109.5 . . ?
C24 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C7 N1 S1 119.3(3) . . ?
C10 N1 C7 110.7(4) . . ?
C10 N1 S1 121.8(3) . . ?
C22 N2 S2 120.8(3) . . ?
C25 N2 C22 111.2(3) . . ?
C25 N2 S2 119.7(3) . . ?
C15 O4 H4 110(6) . . ?
C29 O8 H8A 116(5) . . ?
N1 S1 C1 108.52(18) . . ?
O1 S1 C1 107.80(19) . . ?
O1 S1 N1 106.6(2) . . ?
O1 S1 O2 119.8(2) . . ?
O2 S1 C1 106.6(2) . . ?
O2 S1 N1 107.15(19) . . ?
N2 S2 C16 108.17(18) . . ?
O5 S2 C16 107.7(2) . . ?
O5 S2 N2 106.9(2) . . ?
O5 S2 O6 120.1(2) . . ?
O6 S2 C16 106.92(19) . . ?
O6 S2 N2 106.6(2) . . ?

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
C1 C2 C3 C4 -1.3(6) . . . . ?
C2 C1 C6 C5 1.7(6) . . . . ?
C2 C1 S1 N1 74.5(4) . . . . ?
C2 C1 S1 O1 -170.5(3) . . . . ?
C2 C1 S1 O2 -40.6(4) . . . . ?
C2 C3 C4 C5 1.3(6) . . . . ?
C2 C3 C4 C11 -177.9(4) . . . . ?
C3 C4 C5 C6 0.3(6) . . . . ?
C4 C5 C6 C1 -1.8(6) . . . . ?
C6 C1 C2 C3 -0.2(6) . . . . ?
C6 C1 S1 N1 -104.7(4) . . . . ?
C6 C1 S1 O1 10.4(4) . . . . ?
C6 C1 S1 O2 140.2(3) . . . . ?
C7 C8 C9 C10 40.2(4) . . . . ?
C7 C8 C9 C13 164.7(4) . . . . ?
C7 N1 S1 C1 73.0(4) . . . . ?
C7 N1 S1 O1 -42.9(4) . . . . ?
C7 N1 S1 O2 -172.3(3) . . . . ?
C8 C7 N1 C10 -0.5(5) . . . . ?
C8 C7 N1 S1 -149.5(3) . . . . ?
C8 C9 C10 N1 -39.6(4) . . . . ?
C8 C9 C13 C14 -178.7(4) . . . . ?
C9 C10 N1 C7 25.6(5) . . . . ?
C9 C10 N1 S1 173.7(3) . . . . ?
C9 C13 C14 C15 -168.1(4) . . . . ?
C10 C9 C13 C14 -62.6(5) . . . . ?
C10 N1 S1 C1 -72.5(4) . . . . ?
C10 N1 S1 O1 171.6(3) . . . . ?
C10 N1 S1 O2 42.2(4) . . . . ?
C11 C4 C5 C6 179.5(4) . . . . ?
C12 C8 C9 C10 165.5(4) . . . . ?
C12 C8 C9 C13 -70.1(5) . . . . ?
C13 C9 C10 N1 -161.6(4) . . . . ?
C13 C14 C15 O3 38.0(6) . . . . ?
C13 C14 C15 O4 -142.1(4) . . . . ?
C16 C17 C18 C19 0.3(6) . . . . ?
C17 C16 C21 C20 -0.1(6) . . . . ?
C17 C16 S2 N2 100.1(4) . . . . ?
C17 C16 S2 O5 -144.7(3) . . . . ?
C17 C16 S2 O6 -14.4(4) . . . . ?
C17 C18 C19 C20 0.7(6) . . . . ?
C17 C18 C19 C26 -178.9(4) . . . . ?
C18 C19 C20 C21 -1.4(6) . . . . ?
C19 C20 C21 C16 1.1(6) . . . . ?
C21 C16 C17 C18 -0.6(6) . . . . ?
C21 C16 S2 N2 -79.4(4) . . . . ?
C21 C16 S2 O5 35.8(4) . . . . ?
C21 C16 S2 O6 166.2(3) . . . . ?
C22 C23 C24 C25 39.3(4) . . . . ?
C22 C23 C24 C30 162.6(4) . . . . ?
C22 C23 C27 C28 -60.2(5) . . . . ?
C22 N2 S2 C16 75.1(4) . . . . ?
C22 N2 S2 O5 -40.7(4) . . . . ?
C22 N2 S2 O6 -170.3(3) . . . . ?
C23 C22 N2 C25 -1.4(5) . . . . ?
C23 C22 N2 S2 -149.7(3) . . . . ?
C23 C24 C25 N2 -39.1(4) . . . . ?
C23 C27 C28 C29 -155.6(4) . . . . ?
C24 C23 C27 C28 -179.5(4) . . . . ?
C24 C25 N2 C22 25.4(5) . . . . ?
C24 C25 N2 S2 174.0(3) . . . . ?
C25 N2 S2 C16 -70.5(4) . . . . ?
C25 N2 S2 O5 173.7(3) . . . . ?
C25 N2 S2 O6 44.1(4) . . . . ?
C26 C19 C20 C21 178.2(4) . . . . ?
C27 C23 C24 C25 164.3(4) . . . . ?
C27 C23 C24 C30 -72.4(5) . . . . ?
C27 C28 C29 O7 7.5(7) . . . . ?
C27 C28 C29 O8 -175.1(4) . . . . ?
C30 C24 C25 N2 -163.9(4) . . . . ?
N1 C7 C8 C9 -24.8(4) . . . . ?
N1 C7 C8 C12 -151.0(4) . . . . ?
N2 C22 C23 C24 -23.5(4) . . . . ?
N2 C22 C23 C27 -148.2(4) . . . . ?
S1 C1 C2 C3 -179.3(3) . . . . ?
S1 C1 C6 C5 -179.1(3) . . . . ?
S2 C16 C17 C18 179.9(3) . . . . ?
S2 C16 C21 C20 179.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cu_ncsu_pn76_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2519171'
loop_
_audit_author_name
_audit_author_address
'Phattananawee Nalaoh'
;Department of Chemistry, the University of Tennessee
United States of America
;
_audit_update_record             
;
2025-12-28 deposited with the CCDC.	2026-03-26 downloaded from the CCDC.
;
_audit_creation_date             2024-05-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H15 Br2 N O'
_chemical_formula_sum            'C14 H15 Br2 N O'
_chemical_formula_weight         373.09
_chemical_absolute_configuration syn
_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'
Br Br -0.6763 1.2805 '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                   4.9130(6)
_cell_length_b                   11.0001(14)
_cell_length_c                   13.3169(17)
_cell_angle_alpha                90
_cell_angle_beta                 93.040(5)
_cell_angle_gamma                90
_cell_volume                     718.68(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7465
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.16
_cell_measurement_theta_min      3.32
_shelx_estimated_absorpt_T_max   0.816
_shelx_estimated_absorpt_T_min   0.208
_exptl_absorpt_coefficient_mu    7.053
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.4961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1164 before and 0.0801 after correction.
The Ratio of minimum to maximum transmission is 0.6587.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.324
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9414
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.166
_diffrn_reflns_theta_min         3.323
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.824
_reflns_Friedel_fraction_full    0.924
_reflns_Friedel_fraction_max     0.920
_reflns_number_gt                2454
_reflns_number_total             2522
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.021
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.105
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.09(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2522
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0331
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0551P)²+0.4044P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0870
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.91(4)
 0.09(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All N(H) groups
3.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9)
3.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6)
3.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C14(H14A,H14B,H14C)
3.e :
 C11(H11)
;
_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
C1 C 0.6826(13) 0.5135(6) 0.6788(5) 0.0244(13) Uani 1 1 d . . . . .
C2 C 0.8644(12) 0.4293(6) 0.7245(5) 0.0253(12) Uani 1 1 d . . . . .
H2 H 0.976797 0.380397 0.684932 0.030 Uiso 1 1 calc R U . . .
C3 C 0.8770(13) 0.4189(6) 0.8276(5) 0.0270(13) Uani 1 1 d . . . . .
C4 C 0.7249(14) 0.4913(7) 0.8888(5) 0.0287(13) Uani 1 1 d . . . . .
H4 H 0.738424 0.483752 0.959924 0.034 Uiso 1 1 calc R U . . .
C5 C 0.5519(12) 0.5755(6) 0.8410(5) 0.0274(13) Uani 1 1 d . . . . .
C6 C 0.5280(13) 0.5888(6) 0.7378(5) 0.0260(13) Uani 1 1 d . . . . .
H6 H 0.408775 0.647900 0.707699 0.031 Uiso 1 1 calc R U . . .
C7 C 0.4606(12) 0.5520(6) 0.5103(5) 0.0228(12) Uani 1 1 d . . . . .
C8 C 0.5267(13) 0.5636(6) 0.4007(5) 0.0244(12) Uani 1 1 d . . . . .
H8 H 0.692091 0.513615 0.389021 0.029 Uiso 1 1 calc R U . . .
C9 C 0.2905(13) 0.5195(6) 0.3286(5) 0.0239(12) Uani 1 1 d . . . . .
H9 H 0.144067 0.582676 0.327075 0.029 Uiso 1 1 calc R U . . .
C10 C 0.1734(14) 0.4044(6) 0.3637(5) 0.0268(13) Uani 1 1 d . . . . .
C11 C 0.0692(13) 0.3123(7) 0.3877(5) 0.0310(14) Uani 1 1 d . . . . .
H11 H -0.014197 0.238588 0.406993 0.037 Uiso 1 1 calc R U . . .
C12 C 0.5935(15) 0.6980(7) 0.3816(5) 0.0333(15) Uani 1 1 d . . . . .
H12A H 0.622293 0.710005 0.310074 0.050 Uiso 1 1 calc R U . . .
H12B H 0.759233 0.720584 0.421473 0.050 Uiso 1 1 calc R U . . .
H12C H 0.441537 0.748900 0.401273 0.050 Uiso 1 1 calc R U . . .
C13 C 0.3852(15) 0.5041(7) 0.2206(5) 0.0329(15) Uani 1 1 d . . . . .
H13A H 0.455387 0.582968 0.197226 0.039 Uiso 1 1 calc R U . . .
H13B H 0.537481 0.445040 0.221646 0.039 Uiso 1 1 calc R U . . .
C14 C 0.1584(17) 0.4600(8) 0.1451(5) 0.0367(16) Uani 1 1 d . . . . .
H14A H 0.232108 0.450664 0.078618 0.055 Uiso 1 1 calc R U . . .
H14B H 0.010044 0.519660 0.141358 0.055 Uiso 1 1 calc R U . . .
H14C H 0.088440 0.381585 0.167372 0.055 Uiso 1 1 calc R U . . .
Br1 Br 1.11321(13) 0.30047(5) 0.88887(5) 0.0298(2) Uani 1 1 d . . . . .
Br2 Br 0.34544(13) 0.67903(6) 0.92235(5) 0.0308(2) Uani 1 1 d . . . . .
N1 N 0.6766(11) 0.5216(5) 0.5727(4) 0.0247(11) Uani 1 1 d . . . . .
H1 H 0.83(2) 0.520(9) 0.543(7) 0.037 Uiso 1 1 d . U . . .
O1 O 0.2314(9) 0.5735(5) 0.5404(3) 0.0274(9) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.403(10) . ?
C1 C6 1.394(9) . ?
C1 N1 1.415(9) . ?
C2 H2 0.9500 . ?
C2 C3 1.376(10) . ?
C3 C4 1.387(10) . ?
C3 Br1 1.900(7) . ?
C4 H4 0.9500 . ?
C4 C5 1.388(10) . ?
C5 C6 1.381(9) . ?
C5 Br2 1.901(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.518(9) . ?
C7 N1 1.354(9) . ?
C7 O1 1.237(8) . ?
C8 H8 1.0000 . ?
C8 C9 1.545(9) . ?
C8 C12 1.538(10) . ?
C9 H9 1.0000 . ?
C9 C10 1.477(9) . ?
C9 C13 1.544(9) . ?
C10 C11 1.187(11) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.539(10) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
N1 H1 0.89(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 117.0(6) . . ?
C6 C1 C2 120.1(6) . . ?
C6 C1 N1 122.9(6) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.8(6) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 C4 122.8(6) . . ?
C2 C3 Br1 118.7(5) . . ?
C4 C3 Br1 118.5(5) . . ?
C3 C4 H4 121.6 . . ?
C3 C4 C5 116.8(6) . . ?
C5 C4 H4 121.6 . . ?
C4 C5 Br2 118.1(5) . . ?
C6 C5 C4 123.0(6) . . ?
C6 C5 Br2 118.9(5) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 C1 118.6(6) . . ?
C5 C6 H6 120.7 . . ?
N1 C7 C8 114.2(5) . . ?
O1 C7 C8 122.7(6) . . ?
O1 C7 N1 123.1(6) . . ?
C7 C8 H8 108.7 . . ?
C7 C8 C9 112.3(5) . . ?
C7 C8 C12 107.3(5) . . ?
C9 C8 H8 108.7 . . ?
C12 C8 H8 108.7 . . ?
C12 C8 C9 111.1(5) . . ?
C8 C9 H9 108.1 . . ?
C10 C9 C8 111.4(5) . . ?
C10 C9 H9 108.1 . . ?
C10 C9 C13 110.0(6) . . ?
C13 C9 C8 111.1(5) . . ?
C13 C9 H9 108.1 . . ?
C11 C10 C9 176.5(7) . . ?
C10 C11 H11 180.0 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 H13A 108.9 . . ?
C9 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 C9 113.5(6) . . ?
C14 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 N1 H1 118(6) . . ?
C7 N1 C1 127.0(6) . . ?
C7 N1 H1 114(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -2.5(10) . . . . ?
C1 C2 C3 Br1 177.6(5) . . . . ?
C2 C1 C6 C5 -2.1(9) . . . . ?
C2 C1 N1 C7 150.0(6) . . . . ?
C2 C3 C4 C5 1.0(10) . . . . ?
C3 C4 C5 C6 -0.1(10) . . . . ?
C3 C4 C5 Br2 -178.7(5) . . . . ?
C4 C5 C6 C1 0.6(10) . . . . ?
C6 C1 C2 C3 3.0(10) . . . . ?
C6 C1 N1 C7 -33.3(10) . . . . ?
C7 C8 C9 C10 -43.8(7) . . . . ?
C7 C8 C9 C13 -166.8(6) . . . . ?
C8 C7 N1 C1 174.8(6) . . . . ?
C8 C9 C13 C14 179.9(6) . . . . ?
C10 C9 C13 C14 56.1(8) . . . . ?
C12 C8 C9 C10 -163.9(5) . . . . ?
C12 C8 C9 C13 73.0(7) . . . . ?
Br1 C3 C4 C5 -179.1(5) . . . . ?
Br2 C5 C6 C1 179.2(5) . . . . ?
N1 C1 C2 C3 179.8(6) . . . . ?
N1 C1 C6 C5 -178.7(6) . . . . ?
N1 C7 C8 C9 144.4(6) . . . . ?
N1 C7 C8 C12 -93.2(7) . . . . ?
O1 C7 C8 C9 -38.4(9) . . . . ?
O1 C7 C8 C12 83.9(8) . . . . ?
O1 C7 N1 C1 -2.4(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.91(4)
2 0.09(4)

