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

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

data_jw722a
_database_code_depnum_ccdc_archive 'CCDC 2232201'
loop_
_audit_author_name
_audit_author_address
'Richard J. Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2022-12-21 deposited with the CCDC.	2023-04-24 downloaded from the CCDC.
;
_audit_creation_date             2022-07-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H19 N O'
_chemical_formula_sum            'C16 H19 N O'
_chemical_formula_weight         241.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H19NO
_chemical_oxdiff_usercomment     ZTP-3-143-major
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                   11.82272(18)
_cell_length_b                   8.08217(10)
_cell_length_c                   14.6182(2)
_cell_angle_alpha                90
_cell_angle_beta                 111.1442(18)
_cell_angle_gamma                90
_cell_volume                     1302.78(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10444
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.7150
_cell_measurement_theta_min      4.1360
_shelx_estimated_absorpt_T_max   0.922
_shelx_estimated_absorpt_T_min   0.887
_exptl_absorpt_coefficient_mu    0.592
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.608
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.60a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             520
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.0702
0 -1 0 0.0702
1 0 -1 0.0922
-1 0 1 0.1178
-6 -4 3 0.1077
-1 0 -1 0.1088
1 0 1 0.0478
0 0 -9 0.0860
-1 1 9 0.0690
3 -3 5 0.0591
-4 4 0 0.1121
2 1 -9 0.0758
-3 1 9 0.0822
-7 -2 1 0.0878

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.208
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.14
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0023 1.0003 0.0021 -0.0718 0.1023 -0.1441
0.0023 -1.0003 -0.0021 0.0718 -0.1023 0.1441
0.9998 -0.0002 -1.0019 -0.0984 0.0567 0.0896
-1.0008 -0.0003 1.0005 0.0986 -0.0566 -0.0895
-5.6278 -3.5590 2.9369 0.8925 -0.4260 0.1497
-1.0001 -0.0005 -0.9989 0.1596 0.1339 0.0155
1.0001 0.0005 0.9989 -0.1596 -0.1339 -0.0155
-0.1332 -0.1136 -8.7896 0.2940 0.8309 0.4727
-0.7048 1.0094 8.9625 -0.2557 -0.7232 -0.6416
3.1714 -3.2401 4.5149 -0.3141 -0.8847 0.3463
-4.0498 4.2994 -0.1876 0.2189 0.6150 -0.7583
2.2283 0.9451 -9.3146 -0.0708 0.8977 0.4353
-3.1636 0.9869 9.3026 0.0528 -0.6626 -0.7471
-7.0495 -1.7524 1.2607 0.9972 -0.0263 -0.0747

_exptl_special_details           
;
Data was collected using a Rigaku Synergy S Diffractometer diffractometer equipped 
with an Oxford 800 low-temperature apparatus.  A suitable 
crystal was chosen and mounted on a nylon loop using Paratone oil.  Data  were 
measured based on the Pre-Experiment plugin of CrysAlisPro software.  Cell 
parameters were retrieved using CrysAlisPro software and data reduction was 
performed using the intergration software inside the CrysAlisPro which 
corrects for Lp.  The structure was solved by the direct method using the 
SHELXT program and refined by least squares method on F2, SHELXL,
 incorporated in OLEX2. 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17052
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.158
_diffrn_reflns_theta_min         4.148
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -62.00  25.00   0.50    0.05    --  -47.62  54.00-163.00  174
  2  ω    -60.00 -21.00   0.50    0.10    --  -91.75  54.00-163.00   78
  3  ω    -80.00 -32.00   0.50    0.05    --  -47.62 125.00 -30.00   96
  4  ω    -50.00 -22.00   0.50    0.10    --  -91.75  45.00  30.00   56
  5  ω    -23.00  27.00   0.50    0.05    --  -47.62  19.00 -30.00  100
  6  ω     42.00  99.00   0.50    0.10    --  113.25 -94.00 -30.00  114
  7  ω     42.00  85.00   0.50    0.10    --  113.25 -94.00-180.00   86
  8  ω     58.00  94.00   0.50    0.10    --  113.25 -77.00-180.00   72
  9  ω     65.00  90.00   0.50    0.10    --  113.25 -77.00-150.00   50
 10  ω     46.00  90.00   0.50    0.10    --  113.25 -77.00   0.00   88
 11  ω     42.00  67.00   0.50    0.10    --  113.25 -61.00 -60.00   50
 12  ω     42.00  67.00   0.50    0.10    --  113.25 -61.00 -90.00   50
 13  ω     42.00  67.00   0.50    0.10    --  113.25 -61.00   0.00   50
 14  ω     43.00  69.00   0.50    0.10    --  113.25 -61.00  60.00   52
 15  ω     43.00  98.00   0.50    0.10    --  113.25 -77.00  90.00  110
 16  ω     49.00  90.00   0.50    0.10    --  113.25-125.00 150.00   82
 17  ω     58.00 105.00   0.50    0.10    --  113.25 -77.00 120.00   94
 18  ω     60.00  86.00   0.50    0.05    --   47.62  19.00   0.00   52
 19  ω    133.00 175.00   0.50    0.10    --  113.25  61.00 -90.00   84
 20  ω    129.00 155.00   0.50    0.10    --  113.25  61.00   0.00   52
 21  ω    130.00 174.00   0.50    0.10    --  113.25  61.00  60.00   88
 22  ω    144.00 171.00   0.50    0.10    --  113.25  61.00  90.00   54
 23  ω    149.00 176.00   0.50    0.10    --  113.25  61.00 150.00   54
 24  ω    101.00 148.00   0.50    0.10    --  113.25  30.00   0.00   94
 25  ω    129.00 177.00   0.50    0.10    --  113.25  30.00 120.00   96
 26  ω    103.00 146.00   0.50    0.10    --  113.25  30.00 -60.00   86
 27  ω    122.00 175.00   0.50    0.10    --  113.25  45.00-120.00  106
 28  ω     99.00 178.00   0.50    0.10    --  113.25  54.00-163.00  158
 29  ω     84.00 109.00   0.50    0.05    --   47.62  54.00-163.00   50
 30  ω    118.00 148.00   0.50    0.10    --  113.25  30.00 -90.00   60
 31  ω    150.00 175.00   0.50    0.10    --  113.25  30.00 -30.00   50
 32  ω    101.00 148.00   0.50    0.10    --  113.25  30.00 -30.00   94
 33  ω    101.00 132.00   0.50    0.10    --  113.25  30.00  30.00   62
 34  ω    151.00 178.00   0.50    0.10    --  113.25  30.00  30.00   54
 35  ω    140.00 176.00   0.50    0.10    --  113.25  30.00  90.00   72
 36  ω    102.00 127.00   0.50    0.10    --  113.25  30.00  90.00   50
 37  ω     10.00  36.00   0.50    0.05    --   47.62 -54.00  53.00   52
 38  ω   -119.00 -36.00   0.50    0.05    --  -47.62 -54.00  53.00  166
 39  ω   -144.00-119.00   0.50    0.10    --  -91.75 -54.00  53.00   50
 40  ω   -163.00-138.00   0.50    0.10    --  -91.75 -30.00   0.00   50
 41  ω   -117.00 -88.00   0.50    0.10    --  -91.75 -30.00 -60.00   58
 42  ω   -104.00 -79.00   0.50    0.10    --  -91.75 -29.00 -56.97   50
 43  ω   -105.00 -79.00   0.50    0.10    --  -91.75 -29.00-132.94   52
 44  ω   -108.00 -79.00   0.50    0.10    --  -91.75 -27.00-101.37   58
 45  ω   -115.00 -79.00   0.50    0.10    --  -91.75 -29.00-120.62   72
 46  ω   -108.00 -82.00   0.50    0.10    --  -91.75 -25.00-113.55   52
 47  ω   -108.00 -79.00   0.50    0.10    --  -91.75 -27.00 -83.57   58
 48  ω   -103.00 -78.00   0.50    0.10    --  -91.75 -20.00 -63.23   50
 49  ω    -85.00 -35.00   0.50    0.05    --  -47.62 -19.00 -90.00  100
 50  ω    115.00 143.00   0.50    0.10    --  113.25 125.00 -90.00   56
 51  ω    120.00 152.00   0.50    0.10    --  113.25 125.00-120.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1290381000
_diffrn_orient_matrix_UB_12      -0.0719649000
_diffrn_orient_matrix_UB_13      -0.0305685000
_diffrn_orient_matrix_UB_21      -0.0387575000
_diffrn_orient_matrix_UB_22      0.1023765000
_diffrn_orient_matrix_UB_23      -0.0952645000
_diffrn_orient_matrix_UB_31      0.0369707000
_diffrn_orient_matrix_UB_32      -0.1438290000
_diffrn_orient_matrix_UB_33      -0.0524822000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           1
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2620
_reflns_number_total             2813
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2813
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0401
_refine_ls_restrained_S_all      1.084
_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)+(0.0549P)²+0.3649P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1052
_refine_special_details          
;
The structure was refined by Least Squares SHELXL incorporated 
in Olex2 software program. All non-hydrogen atoms were refined anisotropically. 
Hydrogen atom positions were calculated geometrically and refined using the 
riding model, except for the hydrogen atom on the non-carbon atom(s) which were found 
by difference Fourier methods and refined isotropically when data permits.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.93262(7) 0.23133(10) 0.86614(6) 0.0268(2) Uani 1 1 d . . . . .
N1 N 0.60226(7) 0.28289(11) 0.97597(6) 0.0189(2) Uani 1 1 d . . . . .
C1 C 0.68552(9) 0.22359(12) 0.92933(7) 0.0178(2) Uani 1 1 d . . . . .
H1 H 0.639433 0.163250 0.867323 0.021 Uiso 1 1 calc R U . . .
C2 C 0.76711(10) 0.35899(13) 0.90912(7) 0.0213(2) Uani 1 1 d . . . . .
C3 C 0.87916(9) 0.25201(13) 0.92167(7) 0.0193(2) Uani 1 1 d . . . . .
C4 C 0.90233(9) 0.18503(12) 1.02436(7) 0.0171(2) Uani 1 1 d . . . . .
H4 H 0.973941 0.109883 1.051206 0.021 Uiso 1 1 calc R U . . .
C5 C 0.77689(8) 0.10252(12) 1.00474(7) 0.0155(2) Uani 1 1 d . . . . .
C6 C 0.73149(8) 0.10282(12) 1.08890(7) 0.0159(2) Uani 1 1 d . . . . .
C7 C 0.77487(9) 0.01816(13) 1.17679(7) 0.0196(2) Uani 1 1 d . . . . .
H7 H 0.846237 -0.047168 1.193031 0.024 Uiso 1 1 calc R U . . .
C8 C 0.71244(10) 0.02979(14) 1.24158(7) 0.0233(2) Uani 1 1 d . . . . .
H8 H 0.741865 -0.026866 1.302603 0.028 Uiso 1 1 calc R U . . .
C9 C 0.60769(10) 0.12387(13) 1.21686(8) 0.0231(2) Uani 1 1 d . . . . .
H9 H 0.565245 0.129485 1.260945 0.028 Uiso 1 1 calc R U . . .
C10 C 0.56328(9) 0.21069(13) 1.12831(8) 0.0206(2) Uani 1 1 d . . . . .
H10 H 0.491339 0.274866 1.111775 0.025 Uiso 1 1 calc R U . . .
C11 C 0.62711(9) 0.20076(12) 1.06492(7) 0.0169(2) Uani 1 1 d . . . . .
C13 C 0.82123(10) 0.46600(13) 1.00242(8) 0.0234(2) Uani 1 1 d . . . . .
H13A H 0.756749 0.504822 1.025555 0.028 Uiso 1 1 calc R U . . .
H13B H 0.864044 0.563381 0.989514 0.028 Uiso 1 1 calc R U . . .
C14 C 0.91166(9) 0.34945(13) 1.07980(7) 0.0208(2) Uani 1 1 d . . . . .
H14A H 0.995239 0.393984 1.101772 0.025 Uiso 1 1 calc R U . . .
H14B H 0.887729 0.334885 1.137590 0.025 Uiso 1 1 calc R U . . .
C16 C 0.71288(12) 0.45198(17) 0.81356(9) 0.0348(3) Uani 1 1 d . . . . .
H16A H 0.647723 0.524198 0.816556 0.052 Uiso 1 1 calc R U . . .
H16B H 0.679916 0.372975 0.759580 0.052 Uiso 1 1 calc R U . . .
H16C H 0.775820 0.519100 0.802541 0.052 Uiso 1 1 calc R U . . .
C17 C 0.47699(9) 0.31526(14) 0.91374(8) 0.0253(2) Uani 1 1 d . . . . .
H17A H 0.433108 0.210252 0.895646 0.038 Uiso 1 1 calc R U . . .
H17B H 0.475034 0.373157 0.854281 0.038 Uiso 1 1 calc R U . . .
H17C H 0.438453 0.384178 0.949375 0.038 Uiso 1 1 calc R U . . .
C18 C 0.77499(10) -0.07181(13) 0.96346(8) 0.0217(2) Uani 1 1 d . . . . .
H18A H 0.832410 -0.142237 1.013411 0.033 Uiso 1 1 calc R U . . .
H18B H 0.798191 -0.066743 0.905569 0.033 Uiso 1 1 calc R U . . .
H18C H 0.693168 -0.118131 0.944943 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
O1 C3 1.2068(12) . ?
N1 C1 1.4655(12) . ?
N1 C11 1.3936(13) . ?
N1 C17 1.4552(13) . ?
C1 H1 1.0000 . ?
C1 C2 1.5559(14) . ?
C1 C5 1.5750(13) . ?
C2 C3 1.5365(14) . ?
C2 C13 1.5453(15) . ?
C2 C16 1.5103(14) . ?
C3 C4 1.5248(13) . ?
C4 H4 1.0000 . ?
C4 C5 1.5554(13) . ?
C4 C14 1.5396(13) . ?
C5 C6 1.5092(12) . ?
C5 C18 1.5298(13) . ?
C6 C7 1.3808(13) . ?
C6 C11 1.4001(13) . ?
C7 H7 0.9500 . ?
C7 C8 1.3983(14) . ?
C8 H8 0.9500 . ?
C8 C9 1.3855(16) . ?
C9 H9 0.9500 . ?
C9 C10 1.3976(15) . ?
C10 H10 0.9500 . ?
C10 C11 1.3926(13) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.5612(15) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
C11 N1 C1 109.11(8) . . ?
C11 N1 C17 119.57(8) . . ?
C17 N1 C1 118.10(8) . . ?
N1 C1 H1 110.1 . . ?
N1 C1 C2 115.14(8) . . ?
N1 C1 C5 106.48(7) . . ?
C2 C1 H1 110.1 . . ?
C2 C1 C5 104.73(8) . . ?
C5 C1 H1 110.1 . . ?
C3 C2 C1 98.53(8) . . ?
C3 C2 C13 98.33(8) . . ?
C13 C2 C1 108.28(8) . . ?
C16 C2 C1 116.12(9) . . ?
C16 C2 C3 116.78(9) . . ?
C16 C2 C13 116.12(10) . . ?
O1 C3 C2 129.48(10) . . ?
O1 C3 C4 131.40(10) . . ?
C4 C3 C2 99.11(8) . . ?
C3 C4 H4 115.3 . . ?
C3 C4 C5 98.62(7) . . ?
C3 C4 C14 99.50(8) . . ?
C5 C4 H4 115.3 . . ?
C14 C4 H4 115.3 . . ?
C14 C4 C5 110.47(8) . . ?
C4 C5 C1 103.31(7) . . ?
C6 C5 C1 102.34(7) . . ?
C6 C5 C4 116.41(8) . . ?
C6 C5 C18 111.35(8) . . ?
C18 C5 C1 112.79(8) . . ?
C18 C5 C4 110.18(8) . . ?
C7 C6 C5 129.47(9) . . ?
C7 C6 C11 120.74(9) . . ?
C11 C6 C5 109.72(8) . . ?
C6 C7 H7 120.4 . . ?
C6 C7 C8 119.16(9) . . ?
C8 C7 H7 120.4 . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 120.05(10) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 119.4 . . ?
C8 C9 C10 121.26(9) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 H10 120.8 . . ?
C11 C10 C9 118.34(9) . . ?
C11 C10 H10 120.8 . . ?
N1 C11 C6 111.90(8) . . ?
C10 C11 N1 127.66(9) . . ?
C10 C11 C6 120.42(9) . . ?
C2 C13 H13A 110.7 . . ?
C2 C13 H13B 110.7 . . ?
C2 C13 C14 105.02(8) . . ?
H13A C13 H13B 108.8 . . ?
C14 C13 H13A 110.7 . . ?
C14 C13 H13B 110.7 . . ?
C4 C14 C13 103.83(8) . . ?
C4 C14 H14A 111.0 . . ?
C4 C14 H14B 111.0 . . ?
C13 C14 H14A 111.0 . . ?
C13 C14 H14B 111.0 . . ?
H14A C14 H14B 109.0 . . ?
C2 C16 H16A 109.5 . . ?
C2 C16 H16B 109.5 . . ?
C2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C5 C18 H18A 109.5 . . ?
C5 C18 H18B 109.5 . . ?
C5 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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 C3 C4 C5 -123.88(12) . . . . ?
O1 C3 C4 C14 123.55(12) . . . . ?
N1 C1 C2 C3 148.13(8) . . . . ?
N1 C1 C2 C13 46.37(11) . . . . ?
N1 C1 C2 C16 -86.35(11) . . . . ?
N1 C1 C5 C4 -119.85(8) . . . . ?
N1 C1 C5 C6 1.46(9) . . . . ?
N1 C1 C5 C18 121.21(9) . . . . ?
C1 N1 C11 C6 7.17(11) . . . . ?
C1 N1 C11 C10 -174.51(9) . . . . ?
C1 C2 C3 O1 125.85(11) . . . . ?
C1 C2 C3 C4 -55.25(8) . . . . ?
C1 C2 C13 C14 68.65(10) . . . . ?
C1 C5 C6 C7 179.48(10) . . . . ?
C1 C5 C6 C11 2.65(10) . . . . ?
C2 C1 C5 C4 2.55(9) . . . . ?
C2 C1 C5 C6 123.86(8) . . . . ?
C2 C1 C5 C18 -116.39(9) . . . . ?
C2 C3 C4 C5 57.25(9) . . . . ?
C2 C3 C4 C14 -55.33(9) . . . . ?
C2 C13 C14 C4 0.19(10) . . . . ?
C3 C2 C13 C14 -33.25(9) . . . . ?
C3 C4 C5 C1 -35.99(9) . . . . ?
C3 C4 C5 C6 -147.26(8) . . . . ?
C3 C4 C5 C18 84.74(9) . . . . ?
C3 C4 C14 C13 33.36(9) . . . . ?
C4 C5 C6 C7 -68.69(13) . . . . ?
C4 C5 C6 C11 114.48(9) . . . . ?
C5 C1 C2 C3 31.55(9) . . . . ?
C5 C1 C2 C13 -70.21(9) . . . . ?
C5 C1 C2 C16 157.07(9) . . . . ?
C5 C4 C14 C13 -69.63(9) . . . . ?
C5 C6 C7 C8 -175.84(9) . . . . ?
C5 C6 C11 N1 -6.20(11) . . . . ?
C5 C6 C11 C10 175.35(8) . . . . ?
C6 C7 C8 C9 0.71(15) . . . . ?
C7 C6 C11 N1 176.65(9) . . . . ?
C7 C6 C11 C10 -1.81(14) . . . . ?
C7 C8 C9 C10 -1.02(16) . . . . ?
C8 C9 C10 C11 -0.08(15) . . . . ?
C9 C10 C11 N1 -176.71(9) . . . . ?
C9 C10 C11 C6 1.47(14) . . . . ?
C11 N1 C1 C2 -120.69(9) . . . . ?
C11 N1 C1 C5 -5.12(10) . . . . ?
C11 C6 C7 C8 0.69(15) . . . . ?
C13 C2 C3 O1 -124.12(11) . . . . ?
C13 C2 C3 C4 54.79(9) . . . . ?
C14 C4 C5 C1 67.59(9) . . . . ?
C14 C4 C5 C6 -43.68(11) . . . . ?
C14 C4 C5 C18 -171.68(8) . . . . ?
C16 C2 C3 O1 0.79(17) . . . . ?
C16 C2 C3 C4 179.70(10) . . . . ?
C16 C2 C13 C14 -158.63(9) . . . . ?
C17 N1 C1 C2 98.33(11) . . . . ?
C17 N1 C1 C5 -146.10(9) . . . . ?
C17 N1 C11 C6 147.48(9) . . . . ?
C17 N1 C11 C10 -34.20(15) . . . . ?
C18 C5 C6 C7 58.73(13) . . . . ?
C18 C5 C6 C11 -118.10(9) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id ZTP-3-143-major
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.179
_oxdiff_exptl_absorpt_empirical_full_min 0.869
####################################################################### 
# 
# 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_jw722b
_database_code_depnum_ccdc_archive 'CCDC 2232202'
loop_
_audit_author_name
_audit_author_address
'Richard J. Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2022-12-21 deposited with the CCDC.	2023-04-24 downloaded from the CCDC.
;
_audit_creation_date             2022-07-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H19 N O'
_chemical_formula_sum            'C16 H19 N O'
_chemical_formula_weight         241.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H19NO
_chemical_oxdiff_usercomment     ZTP-3-143-minor
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                   16.0584(2)
_cell_length_b                   6.13979(7)
_cell_length_c                   13.79498(19)
_cell_angle_alpha                90
_cell_angle_beta                 107.5140(15)
_cell_angle_gamma                90
_cell_volume                     1297.07(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11062
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.3760
_cell_measurement_theta_min      2.8620
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.880
_exptl_absorpt_coefficient_mu    0.595
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.576
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.60a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             520
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.0974
0 1 0 0.1089
1 0 -1 0.0307
-7 0 8 0.0232
-10 0 0 0.0846
10 0 0 0.0888
5 0 -9 0.0215
3 0 8 0.0874

_exptl_crystal_recrystallization_method 'Used as recieved'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.057
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0000 -1.0000 -0.0000 0.0346 0.2474 -0.0236
0.0000 1.0000 0.0000 -0.0346 -0.2474 0.0236
1.0000 0.0000 -1.0000 0.1144 -0.0103 0.0596
-6.7663 0.1528 8.2377 -0.8241 0.0225 -0.5659
-9.9342 -0.1269 -0.0014 -0.8274 0.1980 0.5256
9.9460 0.1290 -0.0329 0.8293 -0.1985 -0.5223
5.3693 0.2436 -8.6897 0.7073 -0.0942 0.7006
2.6365 0.3757 7.5415 -0.0232 -0.1858 -0.9823

_exptl_special_details           
;
Data was collected using a Rigaku Synergy S Diffractometer diffractometer equipped 
with an Oxford 800 low-temperature apparatus.  A suitable 
crystal was chosen and mounted on a nylon loop using Paratone oil.  Data  were 
measured based on the Pre-Experiment plugin of CrysAlisPro software.  Cell 
parameters were retrieved using CrysAlisPro software and data reduction was 
performed using the intergration software inside the CrysAlisPro which 
corrects for Lp.  The structure was solved by the direct method using the 
SHELXT program and refined by least squares method on F2, SHELXL,
 incorporated in OLEX2. 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18674
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.865
_diffrn_reflns_theta_min         2.886
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -26.00  23.00   0.50    0.05    --   47.62 -19.00 120.00   98
  2  ω     -2.00  23.00   0.50    0.05    --   47.62 -19.00   0.00   50
  3  ω    -18.00  15.00   0.50    0.05    --   47.62 -19.00 -30.00   66
  4  ω     43.00  68.00   0.50    0.21    --  113.25-125.00-120.00   50
  5  ω     73.00 108.00   0.50    0.21    --  113.25-125.00-120.00   70
  6  ω     68.00  97.00   0.50    0.21    --  113.25-149.00-121.00   58
  7  ω     44.00  89.00   0.50    0.21    --  113.25-125.00-180.00   90
  8  ω     55.00  80.00   0.50    0.05    --   47.62-149.00-121.00   50
  9  ω     43.00  69.00   0.50    0.21    --  113.25-125.00   0.00   52
 10  ω     51.00  76.00   0.50    0.21    --  113.25-123.00  41.00   50
 11  ω     42.00  69.00   0.50    0.21    --  113.25-125.00 150.00   54
 12  ω     55.00  92.00   0.50    0.05    --   47.62-123.00  41.00   74
 13  ω     43.00  68.00   0.50    0.21    --  113.25 -94.00  30.00   50
 14  ω     79.00 104.00   0.50    0.21    --  113.25 -94.00  30.00   50
 15  ω     73.00 100.00   0.50    0.21    --  113.25 -94.00 -30.00   54
 16  ω     79.00 104.00   0.50    0.21    --  113.25 -94.00-150.00   50
 17  ω     44.00 104.00   0.50    0.21    --  113.25-102.00-170.31  120
 18  ω     42.00  67.00   0.50    0.21    --  113.25 -94.00-150.00   50
 19  ω     43.00  68.00   0.50    0.21    --  113.25 -94.00 -90.00   50
 20  ω     73.00 104.00   0.50    0.21    --  113.25 -94.00 -90.00   62
 21  ω     42.00  68.00   0.50    0.21    --  113.25 -94.00 -30.00   52
 22  ω     42.00 103.00   0.50    0.21    --  113.25 -94.00  60.00  122
 23  ω     74.00 102.00   0.50    0.21    --  113.25 -94.00  90.00   56
 24  ω     70.00 103.00   0.50    0.21    --  113.25 -94.00 120.00   66
 25  ω     44.00  69.00   0.50    0.21    --  113.25 -94.00  90.00   50
 26  ω     74.00 104.00   0.50    0.21    --  113.25 -94.00   0.00   60
 27  ω     78.00 104.00   0.50    0.21    --  113.25 -94.00 -60.00   52
 28  ω     51.00  98.00   0.50    0.21    --  113.25 -94.00-120.00   94
 29  ω     42.00  69.00   0.50    0.21    --  113.25 -61.00-180.00   54
 30  ω     42.00  67.00   0.50    0.21    --  113.25 -61.00-120.00   50
 31  ω     42.00  68.00   0.50    0.21    --  113.25 -61.00 -90.00   52
 32  ω     45.00  70.00   0.50    0.21    --  113.25 -61.00 -60.00   50
 33  ω     42.00  69.00   0.50    0.21    --  113.25 -61.00  30.00   54
 34  ω     42.00  68.00   0.50    0.21    --  113.25 -61.00  90.00   52
 35  ω    109.00 134.00   0.50    0.21    --  113.25  30.00-120.00   50
 36  ω    144.00 170.00   0.50    0.21    --  113.25  61.00-180.00   52
 37  ω    128.00 178.00   0.50    0.21    --  113.25  77.00-150.00  100
 38  ω    142.00 175.00   0.50    0.21    --  113.25  61.00-120.00   66
 39  ω    122.00 176.00   0.50    0.21    --  113.25  45.00 -60.00  108
 40  ω    131.00 157.00   0.50    0.21    --  113.25  45.00   0.00   52
 41  ω    130.00 176.00   0.50    0.21    --  113.25  61.00   0.00   92
 42  ω    122.00 175.00   0.50    0.21    --  113.25  45.00  60.00  106
 43  ω    122.00 147.00   0.50    0.21    --  113.25  45.00 120.00   50
 44  ω    144.00 173.00   0.50    0.21    --  113.25  77.00 150.00   58
 45  ω     99.00 134.00   0.50    0.21    --  113.25 123.00 122.00   70
 46  ω    116.00 155.00   0.50    0.21    --  113.25 125.00   0.00   78
 47  ω     98.00 123.00   0.50    0.21    --  113.25 149.00 -74.00   50
 48  ω    -42.00  20.00   0.50    0.05    --  -47.62  37.00 -90.00  124
 49  ω    -50.00 -20.00   0.50    0.21    --  -91.75  45.00 -60.00   60
 50  ω    -19.00   9.00   0.50    0.05    --  -47.62  19.00 -30.00   56
 51  ω    -20.00   6.00   0.50    0.05    --  -47.62  19.00  60.00   52
 52  ω    -26.00  25.00   0.50    0.05    --  -47.62  19.00 120.00  102
 53  ω    -52.00 -27.00   0.50    0.21    --  -91.75 123.00 122.00   50
 54  ω    -82.00 -20.00   0.50    0.05    --  -47.62 123.00 122.00  124
 55  ω    -88.00 -63.00   0.50    0.05    --  -47.62 149.00 -74.00   50
 56  ω    -88.00 -63.00   0.50    0.21    --  -91.75 149.00 -74.00   50
 57  ω   -160.00-124.00   0.50    0.21    --  -91.75 -45.00 -60.00   72
 58  ω   -159.00-122.00   0.50    0.21    --  -91.75 -45.00 -30.00   74
 59  ω   -157.00-131.00   0.50    0.21    --  -91.75 -61.00   0.00   52
 60  ω   -151.00-125.00   0.50    0.21    --  -91.75 -45.00  90.00   52
 61  ω   -163.00-125.00   0.50    0.21    --  -91.75 -45.00 150.00   76
 62  ω   -140.00 -77.00   0.50    0.21    --  -91.75-123.00  41.00  126
 63  ω   -112.00 -61.00   0.50    0.05    --  -47.62-149.00-121.00  102
 64  ω   -127.00-101.00   0.50    0.21    --  -91.75-149.00-121.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0837300000
_diffrn_orient_matrix_UB_12      -0.0346023000
_diffrn_orient_matrix_UB_13      -0.0306284000
_diffrn_orient_matrix_UB_21      -0.0167715000
_diffrn_orient_matrix_UB_22      -0.2474029000
_diffrn_orient_matrix_UB_23      -0.0064549000
_diffrn_orient_matrix_UB_31      -0.0531942000
_diffrn_orient_matrix_UB_32      0.0235874000
_diffrn_orient_matrix_UB_33      -0.1128324000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           1
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2570
_reflns_number_total             2798
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0014(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2798
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0376
_refine_ls_restrained_S_all      1.078
_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)+(0.0500P)²+0.3692P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1011
_refine_special_details          
;
The structure was refined by Least Squares SHELXL incorporated 
in Olex2 software program. All non-hydrogen atoms were refined anisotropically. 
Hydrogen atom positions were calculated geometrically and refined using the 
riding model, except for the hydrogen atom on the non-carbon atom(s) which were found 
by difference Fourier methods and refined isotropically when data permits.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C8(H8), C9(H9), C7(H7)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.13778(5) 0.97166(12) 0.79597(6) 0.02629(19) Uani 1 1 d . . . . .
N1 N 0.29194(5) 0.52445(14) 0.84596(6) 0.0206(2) Uani 1 1 d . . . . .
C11 C 0.35320(6) 0.67335(16) 0.83388(7) 0.0190(2) Uani 1 1 d . . . . .
C1 C 0.22241(6) 0.49766(16) 0.74957(7) 0.0187(2) Uani 1 1 d . . . . .
H1 H 0.219179 0.343555 0.725248 0.022 Uiso 1 1 calc R U . . .
C3 C 0.14446(6) 0.82135(16) 0.74242(8) 0.0200(2) Uani 1 1 d . . . . .
C6 C 0.32767(6) 0.76749(16) 0.73702(7) 0.0190(2) Uani 1 1 d . . . . .
C5 C 0.24531(6) 0.65832(16) 0.67120(7) 0.0193(2) Uani 1 1 d . . . . .
C16 C 0.10576(7) 0.50896(18) 0.84675(8) 0.0252(2) Uani 1 1 d . . . . .
H16A H 0.099025 0.350311 0.846666 0.038 Uiso 1 1 calc R U . . .
H16B H 0.050232 0.578390 0.844383 0.038 Uiso 1 1 calc R U . . .
H16C H 0.150911 0.553901 0.908771 0.038 Uiso 1 1 calc R U . . .
C10 C 0.43116(7) 0.73464(18) 0.90565(8) 0.0232(2) Uani 1 1 d . . . . .
H10 H 0.449330 0.669247 0.971075 0.028 Uiso 1 1 calc R U . . .
C2 C 0.13217(6) 0.57725(16) 0.75487(7) 0.0199(2) Uani 1 1 d . . . . .
C17 C 0.31931(7) 0.33414(18) 0.91025(8) 0.0263(2) Uani 1 1 d . . . . .
H17A H 0.356419 0.241958 0.882425 0.039 Uiso 1 1 calc R U . . .
H17B H 0.267752 0.251487 0.912612 0.039 Uiso 1 1 calc R U . . .
H17C H 0.352235 0.380601 0.979085 0.039 Uiso 1 1 calc R U . . .
C8 C 0.45605(7) 0.99243(18) 0.78374(9) 0.0259(2) Uani 1 1 d . . . . .
H8 H 0.491209 1.102429 0.767392 0.031 Uiso 1 1 calc R U . . .
C9 C 0.48169(7) 0.89457(18) 0.87869(8) 0.0255(2) Uani 1 1 d . . . . .
H9 H 0.535131 0.937664 0.926665 0.031 Uiso 1 1 calc R U . . .
C13 C 0.06636(7) 0.52480(18) 0.64996(8) 0.0250(2) Uani 1 1 d . . . . .
H13A H 0.005589 0.534481 0.652777 0.030 Uiso 1 1 calc R U . . .
H13B H 0.076401 0.376631 0.627461 0.030 Uiso 1 1 calc R U . . .
C7 C 0.37800(7) 0.92799(18) 0.71218(8) 0.0234(2) Uani 1 1 d . . . . .
H7 H 0.359739 0.994175 0.646926 0.028 Uiso 1 1 calc R U . . .
C4 C 0.16634(6) 0.81747(17) 0.64216(8) 0.0217(2) Uani 1 1 d . . . . .
H4 H 0.178028 0.962983 0.616387 0.026 Uiso 1 1 calc R U . . .
C14 C 0.08375(7) 0.70082(19) 0.57654(8) 0.0269(2) Uani 1 1 d . . . . .
H14A H 0.094036 0.632469 0.516149 0.032 Uiso 1 1 calc R U . . .
H14B H 0.034070 0.803304 0.553883 0.032 Uiso 1 1 calc R U . . .
C18 C 0.26259(7) 0.54134(19) 0.58135(8) 0.0264(2) Uani 1 1 d . . . . .
H18A H 0.312950 0.444215 0.606276 0.040 Uiso 1 1 calc R U . . .
H18B H 0.274821 0.649016 0.534973 0.040 Uiso 1 1 calc R U . . .
H18C H 0.211093 0.455802 0.545177 0.040 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 C3 1.2069(13) . ?
N1 C11 1.3893(13) . ?
N1 C1 1.4657(12) . ?
N1 C17 1.4528(13) . ?
C11 C6 1.3992(14) . ?
C11 C10 1.3938(14) . ?
C1 H1 1.0000 . ?
C1 C5 1.5863(14) . ?
C1 C2 1.5517(13) . ?
C3 C2 1.5281(14) . ?
C3 C4 1.5263(14) . ?
C6 C5 1.5165(13) . ?
C6 C7 1.3815(14) . ?
C5 C4 1.5549(14) . ?
C5 C18 1.5286(14) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C16 C2 1.5118(14) . ?
C10 H10 0.9500 . ?
C10 C9 1.3938(16) . ?
C2 C13 1.5475(13) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C8 H8 0.9500 . ?
C8 C9 1.3862(16) . ?
C8 C7 1.3990(15) . ?
C9 H9 0.9500 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.5627(16) . ?
C7 H7 0.9500 . ?
C4 H4 1.0000 . ?
C4 C14 1.5391(14) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
C11 N1 C1 109.80(8) . . ?
C11 N1 C17 120.49(8) . . ?
C17 N1 C1 118.13(8) . . ?
N1 C11 C6 111.82(8) . . ?
N1 C11 C10 127.56(9) . . ?
C10 C11 C6 120.61(9) . . ?
N1 C1 H1 111.0 . . ?
N1 C1 C5 106.19(7) . . ?
N1 C1 C2 112.90(8) . . ?
C5 C1 H1 111.0 . . ?
C2 C1 H1 111.0 . . ?
C2 C1 C5 104.34(8) . . ?
O1 C3 C2 130.01(10) . . ?
O1 C3 C4 130.82(10) . . ?
C4 C3 C2 99.17(8) . . ?
C11 C6 C5 109.96(9) . . ?
C7 C6 C11 120.42(9) . . ?
C7 C6 C5 129.54(9) . . ?
C6 C5 C1 101.90(7) . . ?
C6 C5 C4 111.91(8) . . ?
C6 C5 C18 110.78(8) . . ?
C4 C5 C1 103.18(8) . . ?
C18 C5 C1 113.35(8) . . ?
C18 C5 C4 114.79(8) . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C2 C16 H16A 109.5 . . ?
C2 C16 H16B 109.5 . . ?
C2 C16 H16C 109.5 . . ?
C11 C10 H10 120.9 . . ?
C9 C10 C11 118.12(9) . . ?
C9 C10 H10 120.9 . . ?
C3 C2 C1 98.60(8) . . ?
C3 C2 C13 100.02(8) . . ?
C16 C2 C1 116.98(9) . . ?
C16 C2 C3 116.39(9) . . ?
C16 C2 C13 116.20(9) . . ?
C13 C2 C1 105.96(8) . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C9 C8 H8 120.2 . . ?
C9 C8 C7 119.51(10) . . ?
C7 C8 H8 120.2 . . ?
C10 C9 H9 119.1 . . ?
C8 C9 C10 121.75(10) . . ?
C8 C9 H9 119.1 . . ?
C2 C13 H13A 110.8 . . ?
C2 C13 H13B 110.8 . . ?
C2 C13 C14 104.91(8) . . ?
H13A C13 H13B 108.8 . . ?
C14 C13 H13A 110.8 . . ?
C14 C13 H13B 110.8 . . ?
C6 C7 C8 119.57(10) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C3 C4 C5 99.71(8) . . ?
C3 C4 H4 115.3 . . ?
C3 C4 C14 98.49(8) . . ?
C5 C4 H4 115.3 . . ?
C14 C4 C5 110.53(8) . . ?
C14 C4 H4 115.3 . . ?
C13 C14 H14A 111.1 . . ?
C13 C14 H14B 111.1 . . ?
C4 C14 C13 103.36(8) . . ?
C4 C14 H14A 111.1 . . ?
C4 C14 H14B 111.1 . . ?
H14A C14 H14B 109.1 . . ?
C5 C18 H18A 109.5 . . ?
C5 C18 H18B 109.5 . . ?
C5 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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 C3 C2 C1 -124.58(11) . . . . ?
O1 C3 C2 C16 1.39(16) . . . . ?
O1 C3 C2 C13 127.41(11) . . . . ?
O1 C3 C4 C5 125.05(11) . . . . ?
O1 C3 C4 C14 -122.28(11) . . . . ?
N1 C11 C6 C5 -6.29(11) . . . . ?
N1 C11 C6 C7 176.70(9) . . . . ?
N1 C11 C10 C9 -177.45(10) . . . . ?
N1 C1 C5 C6 -1.85(9) . . . . ?
N1 C1 C5 C4 -118.02(8) . . . . ?
N1 C1 C5 C18 117.22(9) . . . . ?
N1 C1 C2 C3 80.19(9) . . . . ?
N1 C1 C2 C16 -45.37(12) . . . . ?
N1 C1 C2 C13 -176.74(8) . . . . ?
C11 N1 C1 C5 -1.65(10) . . . . ?
C11 N1 C1 C2 -115.39(9) . . . . ?
C11 C6 C5 C1 4.77(10) . . . . ?
C11 C6 C5 C4 114.40(9) . . . . ?
C11 C6 C5 C18 -116.11(9) . . . . ?
C11 C6 C7 C8 1.59(15) . . . . ?
C11 C10 C9 C8 0.27(16) . . . . ?
C1 N1 C11 C6 4.96(11) . . . . ?
C1 N1 C11 C10 -176.29(10) . . . . ?
C1 C5 C4 C3 32.42(9) . . . . ?
C1 C5 C4 C14 -70.53(10) . . . . ?
C1 C2 C13 C14 -75.34(10) . . . . ?
C3 C2 C13 C14 26.69(10) . . . . ?
C3 C4 C14 C13 -39.22(9) . . . . ?
C6 C11 C10 C9 1.20(15) . . . . ?
C6 C5 C4 C3 -76.39(9) . . . . ?
C6 C5 C4 C14 -179.33(8) . . . . ?
C5 C1 C2 C3 -34.68(9) . . . . ?
C5 C1 C2 C16 -160.23(8) . . . . ?
C5 C1 C2 C13 68.40(9) . . . . ?
C5 C6 C7 C8 -174.77(10) . . . . ?
C5 C4 C14 C13 64.55(10) . . . . ?
C16 C2 C13 C14 152.85(9) . . . . ?
C10 C11 C6 C5 174.87(9) . . . . ?
C10 C11 C6 C7 -2.15(15) . . . . ?
C2 C1 C5 C6 117.65(8) . . . . ?
C2 C1 C5 C4 1.49(9) . . . . ?
C2 C1 C5 C18 -123.28(9) . . . . ?
C2 C3 C4 C5 -55.64(8) . . . . ?
C2 C3 C4 C14 57.03(9) . . . . ?
C2 C13 C14 C4 7.80(10) . . . . ?
C17 N1 C11 C6 147.48(9) . . . . ?
C17 N1 C11 C10 -33.78(15) . . . . ?
C17 N1 C1 C5 -145.16(9) . . . . ?
C17 N1 C1 C2 101.10(10) . . . . ?
C9 C8 C7 C6 -0.13(16) . . . . ?
C7 C6 C5 C1 -178.57(10) . . . . ?
C7 C6 C5 C4 -68.94(13) . . . . ?
C7 C6 C5 C18 60.56(14) . . . . ?
C7 C8 C9 C10 -0.81(16) . . . . ?
C4 C3 C2 C1 56.10(8) . . . . ?
C4 C3 C2 C16 -177.93(8) . . . . ?
C4 C3 C2 C13 -51.90(9) . . . . ?
C18 C5 C4 C3 156.24(9) . . . . ?
C18 C5 C4 C14 53.29(12) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id ZTP-3-143-minor
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.179
_oxdiff_exptl_absorpt_empirical_full_min 0.862
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_jw622b
_database_code_depnum_ccdc_archive 'CCDC 2232204'
loop_
_audit_author_name
_audit_author_address
'Richard J. Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2022-12-21 deposited with the CCDC.	2023-04-24 downloaded from the CCDC.
;
_audit_creation_date             2022-06-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H18 Br N O'
_chemical_formula_sum            'C16 H18 Br N O'
_chemical_formula_weight         320.22
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H19NO
_chemical_oxdiff_usercomment     ZTP-3-187-minor
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           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                   13.68696(11)
_cell_length_b                   6.65657(6)
_cell_length_c                   15.48510(13)
_cell_angle_alpha                90
_cell_angle_beta                 101.5354(8)
_cell_angle_gamma                90
_cell_volume                     1382.32(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14864
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.2500
_cell_measurement_theta_min      2.8720
_shelx_estimated_absorpt_T_max   0.548
_shelx_estimated_absorpt_T_min   0.334
_exptl_absorpt_coefficient_mu    3.972
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.421
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.59a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 0 0.0993
1 0 0 0.0993
-2 0 5 0.0840
2 0 -5 0.0877
0 1 0 0.1781
0 -1 0 0.1762
1 0 1 0.0957
-1 0 -1 0.0957
5 0 -3 0.0820
1 2 5 0.1392
3 -4 -2 0.1723
1 2 -1 0.1482
-4 0 5 0.0897

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.354
_exptl_crystal_size_mid          0.205
_exptl_crystal_size_min          0.172
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.9990 0.0002 -0.0006 0.0358 -0.1089 -0.0059
0.9990 -0.0002 0.0006 -0.0358 0.1089 0.0059
-2.0038 0.0036 5.0118 0.5118 0.0305 0.0466
1.9930 0.0015 -5.0027 -0.5108 -0.0313 -0.0454
0.0004 0.9998 -0.0006 -0.0195 -0.0189 0.2298
-0.0004 -0.9998 0.0006 0.0195 0.0189 -0.2298
1.0013 0.0009 0.9974 0.0517 0.1586 0.0176
-1.0013 -0.0009 -0.9974 -0.0517 -0.1586 -0.0176
5.0013 0.0008 -3.0091 -0.4435 0.3956 -0.0048
1.0049 2.0023 4.9948 0.3637 0.3198 0.5237
2.9932 -3.9999 -1.9921 -0.2046 0.3027 -0.9246
1.0071 2.0002 -1.0014 -0.1629 0.0223 0.4542
-4.0023 0.0007 5.0019 0.5827 -0.1878 0.0340

_exptl_special_details           
;
Data was collected using a Rigaku Synergy S Diffractometer diffractometer equipped 
with an Oxford 800 low-temperature apparatus. A suitable 
crystal was chosen and mounted on a nylon loop using Paratone oil. Data were 
measured based on the Pre-Experiment plugin of CrysAlisPro software. Cell 
parameters were retrieved using CrysAlisPro software and data reduction was 
performed using the intergration software inside the CrysAlisPro which 
corrects for Lp. The structure was solved by the direct method using the 
SHELXT program and refined by least squares method on F2, SHELXL,
incorporated in OLEX2.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19284
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.122
_diffrn_reflns_theta_min         3.296
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    130.00 177.00   0.50    0.05    --  113.25 125.00 -90.00   94
  2  ω     -5.00  40.00   0.50    0.05    --   47.62 -37.00-150.00   90
  3  ω    -25.00   0.00   0.50    0.05    --   47.62  -9.00 -42.00   50
  4  ω    -26.00  20.00   0.50    0.05    --   47.62 -19.00 150.00   92
  5  ω     45.00  71.00   0.50    0.05    --  113.25 -77.00  60.00   52
  6  ω     44.00  70.00   0.50    0.05    --  113.25 -61.00  90.00   52
  7  ω     42.00  67.00   0.50    0.05    --  113.25 -61.00   0.00   50
  8  ω     42.00  68.00   0.50    0.05    --  113.25 -61.00 -30.00   52
  9  ω     43.00  68.00   0.50    0.05    --  113.25 -61.00 -60.00   50
 10  ω     42.00  90.00   0.50    0.05    --  113.25 -77.00 -90.00   96
 11  ω     42.00  67.00   0.50    0.05    --  113.25 -61.00-120.00   50
 12  ω     53.00 102.00   0.50    0.05    --  113.25 -94.00-150.00   98
 13  ω     76.00 105.00   0.50    0.05    --  113.25-108.00-142.87   58
 14  ω     43.00  71.00   0.50    0.05    --  113.25-108.00-142.87   56
 15  ω     42.00  68.00   0.50    0.05    --  113.25 -94.00-120.00   52
 16  ω     79.00 104.00   0.50    0.05    --  113.25 -94.00-120.00   50
 17  ω     67.00 104.00   0.50    0.05    --  113.25 -94.00 -90.00   74
 18  ω    130.00 176.00   0.50    0.05    --  113.25  61.00   0.00   92
 19  ω    152.00 177.00   0.50    0.05    --  113.25  61.00 -90.00   50
 20  ω    134.00 178.00   0.50    0.05    --  113.25  61.00  30.00   88
 21  ω    141.00 171.00   0.50    0.05    --  113.25  45.00  60.00   60
 22  ω    145.00 172.00   0.50    0.05    --  113.25  61.00 120.00   54
 23  ω    152.00 178.00   0.50    0.05    --  113.25  45.00 150.00   52
 24  ω    103.00 129.00   0.50    0.05    --  113.25  32.00 -54.70   52
 25  ω    101.00 174.00   0.50    0.05    --  113.25  30.00 -30.00  146
 26  ω    101.00 140.00   0.50    0.05    --  113.25  30.00 -90.00   78
 27  ω    101.00 127.00   0.50    0.05    --  113.25  30.00 -60.00   52
 28  ω    102.00 154.00   0.50    0.05    --  113.25  30.00-120.00  104
 29  ω    137.00 176.00   0.50    0.05    --  113.25  45.00-150.00   78
 30  ω    144.00 170.00   0.50    0.05    --  113.25  30.00-180.00   52
 31  ω    102.00 133.00   0.50    0.05    --  113.25  30.00-180.00   62
 32  ω    102.00 133.00   0.50    0.05    --  113.25  30.00-150.00   62
 33  ω    151.00 178.00   0.50    0.05    --  113.25  30.00 -90.00   54
 34  ω    106.00 132.00   0.50    0.05    --  113.25  30.00 150.00   52
 35  ω    111.00 159.00   0.50    0.05    --  113.25   9.00 131.00   96
 36  ω     30.00  56.00   0.50    0.05    --   47.62   9.00 131.00   52
 37  ω     75.00 100.00   0.50    0.05    --   47.62   9.00 131.00   50
 38  ω     36.00  80.00   0.50    0.05    --   47.62  30.00 -55.06   88
 39  ω     44.00  72.00   0.50    0.05    --   47.62  19.00-150.00   56
 40  ω    -80.00 -30.00   0.50    0.05    --  -47.62 125.00-150.00  100
 41  ω    -82.00 -57.00   0.50    0.05    --  -91.75 125.00-180.00   50
 42  ω    -63.00 -36.00   0.50    0.05    --  -47.62 -31.00-128.18   54
 43  ω    -64.00 -35.00   0.50    0.05    --  -47.62 -31.00 -95.99   58
 44  ω    -75.00 -42.00   0.50    0.05    --  -47.62 -29.00-153.78   66
 45  ω    -76.00 -42.00   0.50    0.05    --  -47.62  -9.00 -42.00   68
 46  ω    -25.00  22.00   0.50    0.05    --  -47.62   9.00 131.00   94
 47  ω    -81.00 -36.00   0.50    0.05    --  -47.62 -29.00 168.38   90
 48  ω   -114.00 -87.00   0.50    0.05    --  -47.62 -29.00 168.38   54
 49  ω    -98.00 -36.00   0.50    0.05    --  -47.62 -29.00 124.62  124
 50  ω   -123.00 -97.00   0.50    0.05    --  -91.75 -31.00 139.65   52
 51  ω   -126.00 -91.00   0.50    0.05    --  -91.75 -30.00 124.84   70
 52  ω   -116.00 -90.00   0.50    0.05    --  -91.75 -30.00 -90.00   52
 53  ω   -113.00 -88.00   0.50    0.05    --  -91.75 -30.00-120.00   50
 54  ω   -115.00 -90.00   0.50    0.05    --  -91.75 -30.00-175.88   50
 55  ω   -117.00 -91.00   0.50    0.05    --  -91.75 -30.00-180.00   52
 56  ω   -107.00 -81.00   0.50    0.05    --  -91.75 -29.00 135.75   52
 57  ω   -107.00 -82.00   0.50    0.05    --  -91.75 -29.00 143.28   50
 58  ω   -106.00 -81.00   0.50    0.05    --  -91.75 -29.00 151.42   50
 59  ω   -105.00 -79.00   0.50    0.05    --  -91.75 -29.00 160.10   52
 60  ω   -104.00 -79.00   0.50    0.05    --  -91.75 -29.00-156.98   50
 61  ω   -104.00 -79.00   0.50    0.05    --  -91.75 -28.00-176.79   50
 62  ω   -104.00 -79.00   0.50    0.05    --  -91.75 -29.00-161.78   50
 63  ω   -112.00 -79.00   0.50    0.05    --  -91.75 -28.00-152.49   66
 64  ω   -104.00 -79.00   0.50    0.05    --  -91.75 -29.00-136.65   50
 65  ω   -144.00-119.00   0.50    0.05    --  -91.75  -9.00 -42.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0358484000
_diffrn_orient_matrix_UB_12      -0.0194052000
_diffrn_orient_matrix_UB_13      0.0878080000
_diffrn_orient_matrix_UB_21      0.1089726000
_diffrn_orient_matrix_UB_22      -0.0188681000
_diffrn_orient_matrix_UB_23      0.0496619000
_diffrn_orient_matrix_UB_31      0.0059392000
_diffrn_orient_matrix_UB_32      0.2298677000
_diffrn_orient_matrix_UB_33      0.0115137000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           1
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2910
_reflns_number_total             2959
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.59a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.59a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.59a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.556
_refine_diff_density_min         -0.620
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2959
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0278
_refine_ls_restrained_S_all      1.126
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0328P)²+1.3770P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0715
_refine_ls_wR_factor_ref         0.0719
_refine_special_details          
;
The structure was refined by Least Squares SHELXL incorporated 
in Olex2 software program. All non-hydrogen atoms were refined anisotropically. 
Hydrogen atom positions were calculated geometrically and refined using the 
riding model, except for the hydrogen atom on the non-carbon atom(s) which were found 
by difference Fourier methods and refined isotropically when data permits.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.80201(2) 0.63026(3) 0.54347(2) 0.02390(8) Uani 1 1 d . . . . .
O1 O 0.90667(10) 0.6468(2) 0.37326(10) 0.0244(3) Uani 1 1 d . . . . .
N1 N 0.64958(11) 0.5230(2) 0.36163(10) 0.0189(3) Uani 1 1 d . . . . .
C1 C 0.81326(14) 0.4247(3) 0.45769(12) 0.0185(3) Uani 1 1 d . . . . .
C2 C 0.87000(13) 0.4883(3) 0.38600(12) 0.0183(4) Uani 1 1 d . . . . .
C3 C 0.86548(13) 0.2884(3) 0.33758(12) 0.0183(4) Uani 1 1 d . . . . .
C4 C 0.74955(13) 0.2515(3) 0.31870(12) 0.0164(3) Uani 1 1 d . . . . .
C5 C 0.71399(13) 0.3572(3) 0.39951(12) 0.0172(4) Uani 1 1 d . . . . .
H5 H 0.677783 0.260882 0.431461 0.021 Uiso 1 1 calc R U . . .
C6 C 0.87113(14) 0.2357(3) 0.49567(13) 0.0224(4) Uani 1 1 d . . . . .
H6A H 0.826147 0.135189 0.514222 0.027 Uiso 1 1 calc R U . . .
H6B H 0.924697 0.269622 0.546649 0.027 Uiso 1 1 calc R U . . .
C7 C 0.91523(14) 0.1569(3) 0.41675(13) 0.0220(4) Uani 1 1 d . . . . .
H7A H 0.988617 0.172901 0.428642 0.026 Uiso 1 1 calc R U . . .
H7B H 0.898756 0.013277 0.405297 0.026 Uiso 1 1 calc R U . . .
C8 C 0.63449(12) 0.5184(3) 0.27063(12) 0.0166(3) Uani 1 1 d . . . . .
C9 C 0.69312(13) 0.3717(3) 0.24101(13) 0.0173(4) Uani 1 1 d . . . . .
C10 C 0.68820(14) 0.3449(3) 0.15187(13) 0.0215(4) Uani 1 1 d . . . . .
H10 H 0.726860 0.243503 0.131459 0.026 Uiso 1 1 calc R U . . .
C11 C 0.62557(15) 0.4689(3) 0.09182(13) 0.0242(4) Uani 1 1 d . . . . .
H11 H 0.623059 0.454427 0.030380 0.029 Uiso 1 1 calc R U . . .
C12 C 0.56745(15) 0.6123(3) 0.12190(13) 0.0229(4) Uani 1 1 d . . . . .
H12 H 0.525063 0.694923 0.080421 0.027 Uiso 1 1 calc R U . . .
C13 C 0.56937(14) 0.6390(3) 0.21163(13) 0.0192(4) Uani 1 1 d . . . . .
H13 H 0.527939 0.735541 0.231771 0.023 Uiso 1 1 calc R U . . .
C14 C 0.91650(14) 0.2828(3) 0.25927(14) 0.0240(4) Uani 1 1 d . . . . .
H14A H 0.905073 0.151822 0.230132 0.036 Uiso 1 1 calc R U . . .
H14B H 0.988283 0.304098 0.279520 0.036 Uiso 1 1 calc R U . . .
H14C H 0.889131 0.388996 0.217551 0.036 Uiso 1 1 calc R U . . .
C15 C 0.72037(14) 0.0291(3) 0.30934(13) 0.0217(4) Uani 1 1 d . . . . .
H15A H 0.647533 0.017113 0.296189 0.033 Uiso 1 1 calc R U . . .
H15B H 0.747400 -0.041266 0.364543 0.033 Uiso 1 1 calc R U . . .
H15C H 0.747505 -0.030763 0.261313 0.033 Uiso 1 1 calc R U . . .
C16 C 0.57304(14) 0.6029(3) 0.40526(13) 0.0227(4) Uani 1 1 d . . . . .
H16A H 0.572602 0.749874 0.401465 0.034 Uiso 1 1 calc R U . . .
H16B H 0.587257 0.562071 0.467316 0.034 Uiso 1 1 calc R U . . .
H16C H 0.507735 0.550590 0.376362 0.034 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.9347(18) . ?
O1 C2 1.201(2) . ?
N1 C5 1.460(2) . ?
N1 C8 1.383(2) . ?
N1 C16 1.456(2) . ?
C1 C2 1.536(2) . ?
C1 C5 1.539(2) . ?
C1 C6 1.539(3) . ?
C2 C3 1.523(3) . ?
C3 C4 1.574(2) . ?
C3 C7 1.549(3) . ?
C3 C14 1.516(3) . ?
C4 C5 1.594(2) . ?
C4 C9 1.521(3) . ?
C4 C15 1.532(3) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.558(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.398(2) . ?
C8 C13 1.396(3) . ?
C9 C10 1.380(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.401(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.382(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.396(3) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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 N1 C5 110.36(14) . . ?
C8 N1 C16 120.40(15) . . ?
C16 N1 C5 121.50(15) . . ?
C2 C1 Br1 114.99(13) . . ?
C2 C1 C5 99.91(14) . . ?
C2 C1 C6 101.86(14) . . ?
C5 C1 Br1 115.21(12) . . ?
C6 C1 Br1 114.91(13) . . ?
C6 C1 C5 108.18(15) . . ?
O1 C2 C1 130.45(17) . . ?
O1 C2 C3 131.59(17) . . ?
C3 C2 C1 97.96(14) . . ?
C2 C3 C4 99.67(13) . . ?
C2 C3 C7 97.81(15) . . ?
C7 C3 C4 109.03(14) . . ?
C14 C3 C2 115.80(16) . . ?
C14 C3 C4 117.14(15) . . ?
C14 C3 C7 114.80(15) . . ?
C3 C4 C5 103.88(14) . . ?
C9 C4 C3 113.47(14) . . ?
C9 C4 C5 101.65(14) . . ?
C9 C4 C15 110.62(15) . . ?
C15 C4 C3 113.72(14) . . ?
C15 C4 C5 112.72(14) . . ?
N1 C5 C1 113.97(15) . . ?
N1 C5 C4 105.84(14) . . ?
N1 C5 H5 111.4 . . ?
C1 C5 C4 102.47(14) . . ?
C1 C5 H5 111.4 . . ?
C4 C5 H5 111.4 . . ?
C1 C6 H6A 111.2 . . ?
C1 C6 H6B 111.2 . . ?
C1 C6 C7 103.06(15) . . ?
H6A C6 H6B 109.1 . . ?
C7 C6 H6A 111.2 . . ?
C7 C6 H6B 111.2 . . ?
C3 C7 C6 104.63(15) . . ?
C3 C7 H7A 110.8 . . ?
C3 C7 H7B 110.8 . . ?
C6 C7 H7A 110.8 . . ?
C6 C7 H7B 110.8 . . ?
H7A C7 H7B 108.9 . . ?
N1 C8 C9 111.78(16) . . ?
N1 C8 C13 126.87(16) . . ?
C13 C8 C9 121.34(17) . . ?
C8 C9 C4 110.00(16) . . ?
C10 C9 C4 129.69(17) . . ?
C10 C9 C8 120.14(17) . . ?
C9 C10 H10 120.4 . . ?
C9 C10 C11 119.26(18) . . ?
C11 C10 H10 120.4 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.03(18) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 119.1 . . ?
C11 C12 C13 121.74(18) . . ?
C13 C12 H12 119.1 . . ?
C8 C13 C12 117.44(17) . . ?
C8 C13 H13 121.3 . . ?
C12 C13 H13 121.3 . . ?
C3 C14 H14A 109.5 . . ?
C3 C14 H14B 109.5 . . ?
C3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C4 C15 H15A 109.5 . . ?
C4 C15 H15B 109.5 . . ?
C4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
Br1 C1 C2 O1 -2.0(3) . . . . ?
Br1 C1 C2 C3 177.64(12) . . . . ?
Br1 C1 C5 N1 47.71(19) . . . . ?
Br1 C1 C5 C4 161.56(12) . . . . ?
Br1 C1 C6 C7 -151.72(12) . . . . ?
O1 C2 C3 C4 -126.0(2) . . . . ?
O1 C2 C3 C7 123.0(2) . . . . ?
O1 C2 C3 C14 0.6(3) . . . . ?
N1 C8 C9 C4 4.4(2) . . . . ?
N1 C8 C9 C10 -179.96(16) . . . . ?
N1 C8 C13 C12 178.60(17) . . . . ?
C1 C2 C3 C4 54.38(15) . . . . ?
C1 C2 C3 C7 -56.55(15) . . . . ?
C1 C2 C3 C14 -179.01(15) . . . . ?
C1 C6 C7 C3 -8.37(18) . . . . ?
C2 C1 C5 N1 -76.08(17) . . . . ?
C2 C1 C5 C4 37.76(16) . . . . ?
C2 C1 C6 C7 -26.73(17) . . . . ?
C2 C3 C4 C5 -30.56(17) . . . . ?
C2 C3 C4 C9 78.96(17) . . . . ?
C2 C3 C4 C15 -153.45(15) . . . . ?
C2 C3 C7 C6 40.32(17) . . . . ?
C3 C4 C5 N1 115.12(15) . . . . ?
C3 C4 C5 C1 -4.57(17) . . . . ?
C3 C4 C9 C8 -111.59(17) . . . . ?
C3 C4 C9 C10 73.3(2) . . . . ?
C4 C3 C7 C6 -62.78(18) . . . . ?
C4 C9 C10 C11 176.02(18) . . . . ?
C5 N1 C8 C9 -6.5(2) . . . . ?
C5 N1 C8 C13 172.84(17) . . . . ?
C5 C1 C2 O1 122.0(2) . . . . ?
C5 C1 C2 C3 -58.41(15) . . . . ?
C5 C1 C6 C7 77.99(17) . . . . ?
C5 C4 C9 C8 -0.71(18) . . . . ?
C5 C4 C9 C10 -175.80(18) . . . . ?
C6 C1 C2 O1 -126.9(2) . . . . ?
C6 C1 C2 C3 52.71(16) . . . . ?
C6 C1 C5 N1 177.85(15) . . . . ?
C6 C1 C5 C4 -68.31(17) . . . . ?
C7 C3 C4 C5 71.25(17) . . . . ?
C7 C3 C4 C9 -179.23(15) . . . . ?
C7 C3 C4 C15 -51.6(2) . . . . ?
C8 N1 C5 C1 117.52(16) . . . . ?
C8 N1 C5 C4 5.69(19) . . . . ?
C8 C9 C10 C11 1.3(3) . . . . ?
C9 C4 C5 N1 -2.90(17) . . . . ?
C9 C4 C5 C1 -122.59(14) . . . . ?
C9 C8 C13 C12 -2.1(3) . . . . ?
C9 C10 C11 C12 -1.8(3) . . . . ?
C10 C11 C12 C13 0.3(3) . . . . ?
C11 C12 C13 C8 1.6(3) . . . . ?
C13 C8 C9 C4 -174.97(16) . . . . ?
C13 C8 C9 C10 0.7(3) . . . . ?
C14 C3 C4 C5 -156.26(16) . . . . ?
C14 C3 C4 C9 -46.7(2) . . . . ?
C14 C3 C4 C15 80.8(2) . . . . ?
C14 C3 C7 C6 163.51(16) . . . . ?
C15 C4 C5 N1 -121.33(16) . . . . ?
C15 C4 C5 C1 118.99(16) . . . . ?
C15 C4 C9 C8 119.22(16) . . . . ?
C15 C4 C9 C10 -55.9(2) . . . . ?
C16 N1 C5 C1 -93.1(2) . . . . ?
C16 N1 C5 C4 155.06(16) . . . . ?
C16 N1 C8 C9 -156.24(17) . . . . ?
C16 N1 C8 C13 23.1(3) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id ZTP-3-187-minor
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.194
_oxdiff_exptl_absorpt_empirical_full_min 0.908
####################################################################### 
# 
# 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_jw622a
_database_code_depnum_ccdc_archive 'CCDC 2232203'
loop_
_audit_author_name
_audit_author_address
'Richard J. Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2022-12-21 deposited with the CCDC.	2023-04-24 downloaded from the CCDC.
;
_audit_creation_date             2022-06-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H18 Br N O'
_chemical_formula_sum            'C16 H18 Br N O'
_chemical_formula_weight         320.22
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H18BrNO
_chemical_oxdiff_usercomment     ZTP-3-187
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           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                   8.88043(12)
_cell_length_b                   10.96832(16)
_cell_length_c                   14.65499(19)
_cell_angle_alpha                90
_cell_angle_beta                 101.3867(13)
_cell_angle_gamma                90
_cell_volume                     1399.35(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12002
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.7790
_cell_measurement_theta_min      4.0450
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.924
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89059
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.58a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             656
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 -1 -8 0.0705
-3 -6 0 0.0768
-2 4 8 0.0307
-5 4 0 0.0588
5 -4 0 0.0648
-1 0 -9 0.0648
5 -1 3 0.0795
5 3 0 0.0778
2 6 -1 0.0695
-2 6 -2 0.0213
0 -5 7 0.1058

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.179
_exptl_crystal_size_mid          0.146
_exptl_crystal_size_min          0.119
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
3.4564 -1.1623 -8.4401 0.0349 -0.0060 -0.9997
-3.1136 -5.9393 -0.0352 0.9632 -0.2325 0.1345
-1.5271 3.6830 8.0826 -0.4738 0.1701 0.8633
-4.5872 4.1236 -0.1368 -0.3007 -0.8519 0.4292
4.5908 -4.1344 0.2468 0.3011 0.8602 -0.4205
-1.1696 -0.0577 -8.7621 0.1413 -0.7580 -0.6386
5.0877 -0.8692 2.6293 -0.1813 0.9657 -0.2010
5.1824 2.9547 -0.2338 -0.6746 0.6386 -0.3765
2.4159 6.4625 -1.2211 -0.9852 0.0243 -0.1742
-2.4392 6.1836 -1.6698 -0.6805 -0.7160 0.1689
-0.2026 -4.7566 7.0083 0.5907 0.6251 0.5124

_exptl_special_details           
;
Data was collected using a Rigaku Synergy S Diffractometer diffractometer equipped 
with an Oxford 800 low-temperature apparatus.  A suitable 
crystal was chosen and mounted on a nylon loop using Paratone oil.  Data  were 
measured based on the Pre-Experiment plugin of CrysAlisPro software.  Cell 
parameters were retrieved using CrysAlisPro software and data reduction was 
performed using the intergration software inside the CrysAlisPro which 
corrects for Lp.  The structure was solved by the direct method using the 
SHELXT program and refined by least squares method on F2, SHELXL,
 incorporated in OLEX2. 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17600
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.789
_diffrn_reflns_theta_min         5.073
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -66.00 -31.00   0.50    0.05    --  -91.75  57.00-180.00   70
  2  ω    -67.00 -33.00   0.50    0.05    --  -91.75  57.00 -90.00   68
  3  ω    -27.00  22.00   0.50    0.05    --  -47.62  19.00 -90.00   98
  4  ω    -22.00  26.00   0.50    0.05    --  -47.62  37.00 -60.00   96
  5  ω    -26.00   8.00   0.50    0.05    --  -47.62  19.00  60.00   68
  6  ω    -25.00  39.00   0.50    0.05    --   47.62 -37.00  30.00  128
  7  ω    -23.00  41.00   0.50    0.05    --   47.62 -37.00 -30.00  128
  8  ω     -6.00  19.00   0.50    0.05    --   47.62 -19.00-150.00   50
  9  ω     -8.00  24.00   0.50    0.05    --   47.62 -19.00-120.00   64
 10  ω     48.00 104.00   0.50    0.05    --  107.19 -99.00  90.00  112
 11  ω     67.00  92.00   0.50    0.05    --  107.19-157.00 178.00   50
 12  ω     68.00 115.00   0.50    0.05    --   47.62-157.00 178.00   94
 13  ω     68.00 101.00   0.50    0.05    --  107.19 -99.00 120.00   66
 14  ω     52.00 100.00   0.50    0.05    --  107.19-125.00   0.00   96
 15  ω     47.00 101.00   0.50    0.05    --  107.19 -99.00   0.00  108
 16  ω     63.00  98.00   0.50    0.05    --  107.19-118.00 -26.00   70
 17  ω     42.00  69.00   0.50    0.05    --  107.19 -99.00  60.00   54
 18  ω     38.00  63.00   0.50    0.05    --   47.62-118.00 -26.00   50
 19  ω     41.00  66.00   0.50    0.05    --  107.19 -99.00-180.00   50
 20  ω     71.00 104.00   0.50    0.05    --  107.19 -99.00-180.00   66
 21  ω     39.00  99.00   0.50    0.05    --  107.19 -99.00-150.00  120
 22  ω     56.00 104.00   0.50    0.05    --  107.19 -99.00-120.00   96
 23  ω     77.00 102.00   0.50    0.05    --  107.19 -99.00  30.00   50
 24  ω     36.00  62.00   0.50    0.05    --  107.19 -99.00  30.00   52
 25  ω     37.00  62.00   0.50    0.05    --  107.19 -57.00  90.00   50
 26  ω     40.00  65.00   0.50    0.05    --  107.19 -57.00  30.00   50
 27  ω     37.00  64.00   0.50    0.05    --  107.19 -57.00   0.00   54
 28  ω     35.00  60.00   0.50    0.05    --  107.19 -57.00-180.00   50
 29  ω     92.00 117.00   0.50    0.05    --  107.19 157.00-145.00   50
 30  ω    126.00 165.00   0.50    0.05    --  107.19  77.00  30.00   78
 31  ω    106.00 149.00   0.50    0.05    --  107.19 118.00  59.00   86
 32  ω    129.00 173.00   0.50    0.05    --  107.19  57.00 120.00   88
 33  ω    -63.00 -37.00   0.50    0.05    --  -91.75 118.00  59.00   52
 34  ω    -40.00 -10.00   0.50    0.05    --  -47.62 118.00  59.00   60
 35  ω    -82.00 -56.00   0.50    0.05    --  -91.75 157.00-145.00   52
 36  ω    -82.00 -30.00   0.50    0.05    --  -91.75 125.00-150.00  104
 37  ω    -92.00 -67.00   0.50    0.05    --  -47.62 157.00-145.00   50
 38  ω   -163.00-114.00   0.50    0.05    --  -91.75 -37.00  60.00   98
 39  ω   -162.00-130.00   0.50    0.05    --  -91.75 -77.00   0.00   64
 40  ω   -161.00-126.00   0.50    0.05    --  -91.75 -77.00 -60.00   70
 41  ω   -152.00-127.00   0.50    0.05    --  -91.75 -57.00 -90.00   50
 42  ω   -154.00-128.00   0.50    0.05    --  -91.75 -77.00 -90.00   52
 43  ω   -163.00-130.00   0.50    0.05    --  -91.75 -57.00-120.00   66
 44  ω   -160.00-130.00   0.50    0.05    --  -91.75 -77.00-150.00   60
 45  ω   -160.00-134.00   0.50    0.05    --  -91.75 -57.00-180.00   52
 46  ω   -160.00-127.00   0.50    0.05    --  -91.75 -57.00-150.00   66
 47  ω   -163.00-127.00   0.50    0.05    --  -91.75 -57.00  30.00   72
 48  ω   -112.00 -86.00   0.50    0.05    --  -91.75-118.00 -26.00   52
 49  ω    -93.00 -55.00   0.50    0.05    --  -47.62-157.00 178.00   76
 50  ω    -93.00 -53.00   0.50    0.05    --  -91.75-157.00 178.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0543358000
_diffrn_orient_matrix_UB_12      -0.1336394000
_diffrn_orient_matrix_UB_13      -0.0079877000
_diffrn_orient_matrix_UB_21      0.1485454000
_diffrn_orient_matrix_UB_22      -0.0391228000
_diffrn_orient_matrix_UB_23      0.0669324000
_diffrn_orient_matrix_UB_31      -0.0794300000
_diffrn_orient_matrix_UB_32      0.0184958000
_diffrn_orient_matrix_UB_33      0.0833681000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           1
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2750
_reflns_number_total             2868
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2868
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0236
_refine_ls_R_factor_gt           0.0227
_refine_ls_restrained_S_all      1.062
_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)+(0.0272P)²+0.8835P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0575
_refine_ls_wR_factor_ref         0.0580
_refine_special_details          
;
The structure was refined by Least Squares SHELXL incorporated 
in Olex2 software program. All non-hydrogen atoms were refined anisotropically. 
Hydrogen atom positions were calculated geometrically and refined using the 
riding model, except for the hydrogen atom on the non-carbon atom(s) which were found 
by difference Fourier methods and refined isotropically when data permits.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Br1 Br 0.13380(2) 0.44615(2) 0.82631(2) 0.02237(7) Uani 1 1 d . . . . .
O1 O 0.47884(13) 0.38737(10) 0.93629(7) 0.0196(2) Uani 1 1 d . . . . .
N1 N 0.32743(15) 0.57974(13) 0.64420(9) 0.0177(3) Uani 1 1 d . . . . .
C1 C 0.32736(17) 0.51295(14) 0.80916(10) 0.0160(3) Uani 1 1 d . . . . .
C2 C 0.36921(17) 0.48460(14) 0.71345(10) 0.0152(3) Uani 1 1 d . . . . .
H2 H 0.326561 0.403974 0.689041 0.018 Uiso 1 1 calc R U . . .
C3 C 0.55089(17) 0.48249(14) 0.73551(10) 0.0145(3) Uani 1 1 d . . . . .
C4 C 0.59131(18) 0.53389(14) 0.83778(10) 0.0148(3) Uani 1 1 d . . . . .
C5 C 0.52552(18) 0.66498(14) 0.83924(11) 0.0170(3) Uani 1 1 d . . . . .
H5A H 0.547444 0.713324 0.786321 0.020 Uiso 1 1 calc R U . . .
H5B H 0.571185 0.707004 0.897973 0.020 Uiso 1 1 calc R U . . .
C6 C 0.34878(18) 0.64872(14) 0.83117(11) 0.0184(3) Uani 1 1 d . . . . .
H6A H 0.316937 0.669508 0.890317 0.022 Uiso 1 1 calc R U . . .
H6B H 0.290197 0.699447 0.780446 0.022 Uiso 1 1 calc R U . . .
C7 C 0.46912(18) 0.46174(14) 0.87551(10) 0.0150(3) Uani 1 1 d . . . . .
C8 C 0.58969(18) 0.56431(14) 0.66038(10) 0.0152(3) Uani 1 1 d . . . . .
C9 C 0.45417(17) 0.61425(14) 0.60869(10) 0.0156(3) Uani 1 1 d . . . . .
C10 C 0.45813(18) 0.69112(15) 0.53375(10) 0.0186(3) Uani 1 1 d . . . . .
H10 H 0.366419 0.724714 0.498243 0.022 Uiso 1 1 calc R U . . .
C11 C 0.60062(19) 0.71738(15) 0.51234(11) 0.0209(3) Uani 1 1 d . . . . .
H11 H 0.605672 0.770777 0.461992 0.025 Uiso 1 1 calc R U . . .
C12 C 0.73498(19) 0.66774(16) 0.56245(11) 0.0214(3) Uani 1 1 d . . . . .
H12 H 0.830655 0.686829 0.546180 0.026 Uiso 1 1 calc R U . . .
C13 C 0.72982(18) 0.58923(16) 0.63726(11) 0.0194(3) Uani 1 1 d . . . . .
H13 H 0.821330 0.553760 0.671500 0.023 Uiso 1 1 calc R U . . .
C14 C 0.61358(19) 0.35324(15) 0.73012(11) 0.0192(3) Uani 1 1 d . . . . .
H14A H 0.572538 0.318626 0.668586 0.029 Uiso 1 1 calc R U . . .
H14B H 0.582381 0.302339 0.778124 0.029 Uiso 1 1 calc R U . . .
H14C H 0.725952 0.356022 0.740194 0.029 Uiso 1 1 calc R U . . .
C15 C 0.75579(18) 0.52030(16) 0.88882(11) 0.0203(3) Uani 1 1 d . . . . .
H15A H 0.765160 0.549341 0.952936 0.030 Uiso 1 1 calc R U . . .
H15B H 0.823134 0.568484 0.857239 0.030 Uiso 1 1 calc R U . . .
H15C H 0.785740 0.434269 0.889384 0.030 Uiso 1 1 calc R U . . .
C16 C 0.17225(18) 0.58741(17) 0.59020(12) 0.0230(3) Uani 1 1 d . . . . .
H16A H 0.149521 0.671968 0.570625 0.035 Uiso 1 1 calc R U . . .
H16B H 0.099545 0.560296 0.628349 0.035 Uiso 1 1 calc R U . . .
H16C H 0.162791 0.535140 0.535125 0.035 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
Br1 C1 1.9301(15) . ?
O1 C7 1.1983(19) . ?
N1 C2 1.452(2) . ?
N1 C9 1.383(2) . ?
N1 C16 1.450(2) . ?
C1 C2 1.552(2) . ?
C1 C6 1.528(2) . ?
C1 C7 1.537(2) . ?
C2 H2 1.0000 . ?
C2 C3 1.582(2) . ?
C3 C4 1.575(2) . ?
C3 C8 1.512(2) . ?
C3 C14 1.531(2) . ?
C4 C5 1.554(2) . ?
C4 C7 1.532(2) . ?
C4 C15 1.511(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.561(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C8 C9 1.401(2) . ?
C8 C13 1.380(2) . ?
C9 C10 1.390(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.393(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.383(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.402(2) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
C9 N1 C2 110.19(12) . . ?
C9 N1 C16 122.36(13) . . ?
C16 N1 C2 120.49(13) . . ?
C2 C1 Br1 114.83(10) . . ?
C6 C1 Br1 114.81(10) . . ?
C6 C1 C2 110.13(12) . . ?
C6 C1 C7 99.81(12) . . ?
C7 C1 Br1 114.72(10) . . ?
C7 C1 C2 100.73(12) . . ?
N1 C2 C1 114.46(13) . . ?
N1 C2 H2 111.0 . . ?
N1 C2 C3 105.25(12) . . ?
C1 C2 H2 111.0 . . ?
C1 C2 C3 103.58(12) . . ?
C3 C2 H2 111.0 . . ?
C4 C3 C2 102.76(11) . . ?
C8 C3 C2 102.26(12) . . ?
C8 C3 C4 116.01(12) . . ?
C8 C3 C14 112.00(12) . . ?
C14 C3 C2 111.70(13) . . ?
C14 C3 C4 111.33(12) . . ?
C5 C4 C3 109.19(12) . . ?
C7 C4 C3 96.54(11) . . ?
C7 C4 C5 100.25(12) . . ?
C15 C4 C3 116.88(13) . . ?
C15 C4 C5 114.45(13) . . ?
C15 C4 C7 117.04(13) . . ?
C4 C5 H5A 110.6 . . ?
C4 C5 H5B 110.6 . . ?
C4 C5 C6 105.58(12) . . ?
H5A C5 H5B 108.8 . . ?
C6 C5 H5A 110.6 . . ?
C6 C5 H5B 110.6 . . ?
C1 C6 C5 102.05(12) . . ?
C1 C6 H6A 111.4 . . ?
C1 C6 H6B 111.4 . . ?
C5 C6 H6A 111.4 . . ?
C5 C6 H6B 111.4 . . ?
H6A C6 H6B 109.2 . . ?
O1 C7 C1 130.45(14) . . ?
O1 C7 C4 131.90(15) . . ?
C4 C7 C1 97.64(12) . . ?
C9 C8 C3 109.33(13) . . ?
C13 C8 C3 129.98(14) . . ?
C13 C8 C9 120.65(14) . . ?
N1 C9 C8 111.44(13) . . ?
N1 C9 C10 127.78(14) . . ?
C10 C9 C8 120.75(14) . . ?
C9 C10 H10 121.0 . . ?
C9 C10 C11 117.98(15) . . ?
C11 C10 H10 121.0 . . ?
C10 C11 H11 119.1 . . ?
C12 C11 C10 121.73(15) . . ?
C12 C11 H11 119.1 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 119.93(15) . . ?
C13 C12 H12 120.0 . . ?
C8 C13 C12 118.94(15) . . ?
C8 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C3 C14 H14A 109.5 . . ?
C3 C14 H14B 109.5 . . ?
C3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C4 C15 H15A 109.5 . . ?
C4 C15 H15B 109.5 . . ?
C4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
Br1 C1 C2 N1 95.47(14) . . . . ?
Br1 C1 C2 C3 -150.51(10) . . . . ?
Br1 C1 C6 C5 164.16(10) . . . . ?
Br1 C1 C7 O1 -0.2(2) . . . . ?
Br1 C1 C7 C4 178.75(10) . . . . ?
N1 C2 C3 C4 110.44(13) . . . . ?
N1 C2 C3 C8 -10.19(15) . . . . ?
N1 C2 C3 C14 -130.12(13) . . . . ?
N1 C9 C10 C11 177.41(15) . . . . ?
C1 C2 C3 C4 -10.05(15) . . . . ?
C1 C2 C3 C8 -130.67(12) . . . . ?
C1 C2 C3 C14 109.39(13) . . . . ?
C2 N1 C9 C8 -10.48(18) . . . . ?
C2 N1 C9 C10 171.49(15) . . . . ?
C2 C1 C6 C5 -64.37(15) . . . . ?
C2 C1 C7 O1 -124.15(17) . . . . ?
C2 C1 C7 C4 54.85(13) . . . . ?
C2 C3 C4 C5 -60.43(14) . . . . ?
C2 C3 C4 C7 42.84(13) . . . . ?
C2 C3 C4 C15 167.68(13) . . . . ?
C2 C3 C8 C9 4.54(15) . . . . ?
C2 C3 C8 C13 -173.02(16) . . . . ?
C3 C4 C5 C6 74.83(14) . . . . ?
C3 C4 C7 O1 118.87(17) . . . . ?
C3 C4 C7 C1 -60.11(12) . . . . ?
C3 C8 C9 N1 3.20(18) . . . . ?
C3 C8 C9 C10 -178.62(14) . . . . ?
C3 C8 C13 C12 178.80(15) . . . . ?
C4 C3 C8 C9 -106.41(15) . . . . ?
C4 C3 C8 C13 76.0(2) . . . . ?
C4 C5 C6 C1 -9.33(15) . . . . ?
C5 C4 C7 O1 -130.22(17) . . . . ?
C5 C4 C7 C1 50.80(13) . . . . ?
C6 C1 C2 N1 -35.99(17) . . . . ?
C6 C1 C2 C3 78.04(15) . . . . ?
C6 C1 C7 O1 123.00(17) . . . . ?
C6 C1 C7 C4 -58.00(13) . . . . ?
C7 C1 C2 N1 -140.71(13) . . . . ?
C7 C1 C2 C3 -26.68(14) . . . . ?
C7 C1 C6 C5 40.98(14) . . . . ?
C7 C4 C5 C6 -25.87(14) . . . . ?
C8 C3 C4 C5 50.23(17) . . . . ?
C8 C3 C4 C7 153.50(13) . . . . ?
C8 C3 C4 C15 -81.66(17) . . . . ?
C8 C9 C10 C11 -0.5(2) . . . . ?
C9 N1 C2 C1 125.85(14) . . . . ?
C9 N1 C2 C3 12.81(16) . . . . ?
C9 C8 C13 C12 1.5(2) . . . . ?
C9 C10 C11 C12 1.0(2) . . . . ?
C10 C11 C12 C13 -0.3(2) . . . . ?
C11 C12 C13 C8 -0.9(2) . . . . ?
C13 C8 C9 N1 -178.98(14) . . . . ?
C13 C8 C9 C10 -0.8(2) . . . . ?
C14 C3 C4 C5 179.87(12) . . . . ?
C14 C3 C4 C7 -76.85(14) . . . . ?
C14 C3 C4 C15 47.98(18) . . . . ?
C14 C3 C8 C9 124.27(14) . . . . ?
C14 C3 C8 C13 -53.3(2) . . . . ?
C15 C4 C5 C6 -152.01(13) . . . . ?
C15 C4 C7 O1 -5.9(2) . . . . ?
C15 C4 C7 C1 175.17(13) . . . . ?
C16 N1 C2 C1 -82.69(18) . . . . ?
C16 N1 C2 C3 164.27(13) . . . . ?
C16 N1 C9 C8 -161.31(15) . . . . ?
C16 N1 C9 C10 20.7(3) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id ZTP-3-187
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.098
_oxdiff_exptl_absorpt_empirical_full_min 0.918
####################################################################### 
# 
# 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_jw922a
_database_code_depnum_ccdc_archive 'CCDC 2232205'
loop_
_audit_author_name
_audit_author_address
'Richard J. Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2022-12-21 deposited with the CCDC.	2023-04-24 downloaded from the CCDC.
;
_audit_creation_date             2022-09-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H19 N O'
_chemical_formula_sum            'C16 H19 N O'
_chemical_formula_weight         241.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15H17NO
_chemical_oxdiff_usercomment     ZTP-4-33
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                   14.04898(14)
_cell_length_b                   6.21142(6)
_cell_length_c                   15.50317(18)
_cell_angle_alpha                90
_cell_angle_beta                 106.1247(12)
_cell_angle_gamma                90
_cell_volume                     1299.65(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    19091
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.7910
_cell_measurement_theta_min      3.2560
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.593
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.584
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.69a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             520
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 2 2 0.0934
3 1 -9 0.0745
-7 0 -4 0.0843
6 -1 5 0.0813
-7 -2 7 0.1274
6 2 -8 0.0698
5 -3 -5 0.0479
-3 -3 6 0.0954
6 3 2 0.0936
-3 1 10 0.0908
-4 -4 0 0.0888
9 1 -2 0.0596

_exptl_crystal_recrystallization_method 'used as receieved'
_exptl_crystal_size_max          0.196
_exptl_crystal_size_mid          0.173
_exptl_crystal_size_min          0.165
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0038 1.9964 2.0057 -0.1302 -0.5203 0.0234
2.6289 1.3612 -9.4540 0.0226 0.0804 0.9947
-7.2936 0.2437 -3.5222 -0.9184 0.2187 0.3270
5.8363 -0.6479 5.4554 0.8140 -0.1926 -0.5452
-6.6045 -1.6022 7.4419 -0.5132 0.1264 -0.8466
5.9887 1.6573 -7.9303 0.4298 -0.1071 0.8949
5.4431 -3.0069 -4.5210 0.6041 0.7895 0.1073
-2.5692 -3.0576 6.4710 -0.0327 0.4318 -0.9012
6.0114 2.5536 2.0406 0.6456 -0.7565 0.0915
-2.5765 0.5517 9.9412 -0.0675 -0.5304 -0.8414
-4.1560 -3.5502 0.0508 -0.3522 0.8558 -0.3783
8.8883 0.7708 -1.9964 0.9312 -0.2218 0.2763

_exptl_special_details           
;
Data was collected using a Rigaku Synergy S Diffractometer diffractometer equipped 
with an Oxford 800 low-temperature apparatus.  A suitable 
crystal was chosen and mounted on a nylon loop using Paratone oil.  Data  were 
measured based on the Pre-Experiment plugin of CrysAlisPro software.  Cell 
parameters were retrieved using CrysAlisPro software and data reduction was 
performed using the intergration software inside the CrysAlisPro which 
corrects for Lp.  The structure was solved by the direct method using the 
SHELXT program and refined by least squares method on F2, SHELXL,
 incorporated in OLEX2. 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            28434
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.079
_diffrn_reflns_theta_min         3.760
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00 -27.00   0.50    0.05    --  -47.44  57.00 120.00   66
  2  ω    -22.00  11.00   0.50    0.05    --  -47.44  57.00 120.00   66
  3  ω    -13.00  14.00   0.50    0.05    --  -47.44  57.00  30.00   54
  4  ω    -21.00  23.00   0.50    0.05    --  -47.44  39.00  15.00   88
  5  ω    -62.00 -26.00   0.50    0.05    --  -47.44  57.00  30.00   72
  6  ω    -70.00  -6.00   0.50    0.05    --  -47.44  77.00-120.00  128
  7  ω     35.00  91.00   0.50    0.05    --   47.44  39.00  15.00  112
  8  ω     38.00  64.00   0.50    0.05    --   47.44  31.00 -13.03   52
  9  ω     37.00  62.00   0.50    0.05    --   47.44  31.00 -74.01   50
 10  ω     37.00  63.00   0.50    0.05    --   47.44  30.00 -86.78   52
 11  ω     36.00  93.00   0.50    0.05    --   47.44  30.00-143.06  114
 12  ω     35.00  60.00   0.50    0.05    --   47.44  31.00  65.58   50
 13  ω     35.00  60.00   0.50    0.05    --   47.44  31.00 116.49   50
 14  ω     38.00  64.00   0.50    0.05    --   47.44  31.00 148.10   52
 15  ω    140.00 165.00   0.50    0.05    --  113.25  77.00 150.00   50
 16  ω    137.00 162.00   0.50    0.05    --  113.25  30.00 120.00   50
 17  ω    140.00 165.00   0.50    0.05    --  113.25  61.00  30.00   50
 18  ω    102.00 168.00   0.50    0.05    --  113.25  30.00  90.00  132
 19  ω    101.00 132.00   0.50    0.05    --  113.25  30.00 120.00   62
 20  ω    101.00 176.00   0.50    0.05    --  113.25  39.00  15.00  150
 21  ω    102.00 127.00   0.50    0.05    --  113.25  30.00 -60.00   50
 22  ω    143.00 178.00   0.50    0.05    --  113.25  30.00 -60.00   70
 23  ω    143.00 173.00   0.50    0.05    --  113.25  61.00-180.00   60
 24  ω    141.00 178.00   0.50    0.05    --  113.25  30.00-150.00   74
 25  ω    101.00 132.00   0.50    0.05    --  113.25  30.00-150.00   62
 26  ω    107.00 169.00   0.50    0.05    --  113.25  30.00-180.00  124
 27  ω    130.00 176.00   0.50    0.05    --  113.25  77.00 -90.00   92
 28  ω    138.00 172.00   0.50    0.05    --  113.25  30.00-120.00   68
 29  ω    101.00 178.00   0.50    0.05    --  113.25  30.00   0.00  154
 30  ω    132.00 177.00   0.50    0.05    --  113.25  30.00  30.00   90
 31  ω    151.00 176.00   0.50    0.05    --  113.25  30.00  60.00   50
 32  ω    102.00 162.00   0.50    0.05    --  113.25  30.00 150.00  120
 33  ω    105.00 133.00   0.50    0.05    --  113.25  30.00  60.00   56
 34  ω    101.00 136.00   0.50    0.05    --  113.25  22.00 -27.80   70
 35  ω    144.00 175.00   0.50    0.05    --  113.25  22.00 -27.80   62
 36  ω    144.00 170.00   0.50    0.05    --  113.25  30.00 -90.00   52
 37  ω    103.00 129.00   0.50    0.05    --  113.25  30.00-120.00   52
 38  ω    103.00 129.00   0.50    0.05    --  113.25  30.00 -90.00   52
 39  ω    109.00 163.00   0.50    0.05    --  113.25 125.00-150.00  108
 40  ω     75.00 101.00   0.50    0.05    --  113.25 -77.00 150.00   52
 41  ω     42.00  70.00   0.50    0.05    --  113.25 -77.00 150.00   56
 42  ω     43.00  69.00   0.50    0.05    --  113.25 -61.00 150.00   52
 43  ω     43.00  69.00   0.50    0.05    --  113.25 -61.00   0.00   52
 44  ω     43.00  70.00   0.50    0.05    --  113.25 -61.00  30.00   54
 45  ω     45.00  70.00   0.50    0.05    --  113.25 -61.00 -60.00   50
 46  ω     44.00  70.00   0.50    0.05    --  113.25 -61.00-120.00   52
 47  ω     42.00  68.00   0.50    0.05    --  113.25 -61.00-150.00   52
 48  ω    -15.00  40.00   0.50    0.05    --   47.44 -39.00-138.00  110
 49  ω     45.00 108.00   0.50    0.05    --  113.25-125.00  30.00  126
 50  ω     51.00 104.00   0.50    0.05    --  113.25 -94.00  60.00  106
 51  ω     44.00 108.00   0.50    0.05    --  113.25-125.00   0.00  128
 52  ω     82.00 108.00   0.50    0.05    --  113.25-125.00 -30.00   52
 53  ω     45.00  77.00   0.50    0.05    --  113.25-125.00 -30.00   64
 54  ω     42.00 102.00   0.50    0.05    --  113.25 -94.00-120.00  120
 55  ω     44.00  70.00   0.50    0.05    --  113.25 -94.00 120.00   52
 56  ω     42.00 102.00   0.50    0.05    --  113.25 -94.00 150.00  120
 57  ω     79.00 104.00   0.50    0.05    --  113.25 -94.00  90.00   50
 58  ω     74.00 100.00   0.50    0.05    --  113.25 -94.00 120.00   52
 59  ω     48.00  74.00   0.50    0.05    --  113.25 -94.00  90.00   52
 60  ω     48.00 104.00   0.50    0.05    --  113.25 -94.00  30.00  112
 61  ω     76.00 101.00   0.50    0.05    --  113.25 -94.00-150.00   50
 62  ω     42.00  71.00   0.50    0.05    --  113.25 -94.00-150.00   58
 63  ω    -61.00 -36.00   0.50    0.05    --  -47.44 -28.00  95.48   50
 64  ω   -121.00 -40.00   0.50    0.05    --  -47.44 -30.00  -1.73  162
 65  ω   -120.00 -34.00   0.50    0.05    --  -47.44 -39.00-138.00  172
 66  ω    -64.00 -39.00   0.50    0.05    --  -47.44 -31.00-120.99   50
 67  ω   -119.00 -75.00   0.50    0.05    --  -47.44 -29.00 -50.34   88
 68  ω    -60.00 -35.00   0.50    0.05    --  -47.44 -29.00 -50.34   50
 69  ω    -45.00 -19.00   0.50    0.05    --  -91.75  39.00  15.00   52
 70  ω    -82.00 -41.00   0.50    0.05    --  -47.44 -30.00  74.21   82
 71  ω   -114.00 -85.00   0.50    0.05    --  -47.44 -30.00  74.21   58
 72  ω   -103.00 -78.00   0.50    0.05    --  -91.75 -25.00  -2.46   50
 73  ω   -114.00 -88.00   0.50    0.05    --  -91.75 -30.00  90.00   52
 74  ω   -116.00 -90.00   0.50    0.05    --  -91.75 -30.00  43.10   52
 75  ω   -114.00 -88.00   0.50    0.05    --  -91.75 -30.00 -69.91   52
 76  ω   -110.00 -78.00   0.50    0.05    --  -91.75 -39.00-138.00   64
 77  ω   -110.00 -82.00   0.50    0.05    --  -91.75 -29.00 -51.31   56
 78  ω   -152.00-126.00   0.50    0.05    --  -91.75 -30.00 -69.91   52
 79  ω   -155.00-129.00   0.50    0.05    --  -91.75 -29.00 -15.51   52
 80  ω   -106.00 -79.00   0.50    0.05    --  -91.75 -29.00 141.30   54
 81  ω   -104.00 -79.00   0.50    0.05    --  -91.75 -29.00 165.25   50
 82  ω   -156.00-130.00   0.50    0.05    --  -91.75 -29.00 141.30   52
 83  ω   -162.00-136.00   0.50    0.05    --  -91.75 -29.00 165.25   52
 84  ω   -106.00 -79.00   0.50    0.05    --  -91.75 -29.00 104.51   54
 85  ω   -104.00 -79.00   0.50    0.05    --  -91.75 -27.00 112.80   50
 86  ω   -105.00 -79.00   0.50    0.05    --  -91.75 -29.00  54.77   52
 87  ω   -165.00-139.00   0.50    0.05    --  -91.75 -27.00 112.80   52
 88  ω   -107.00 -82.00   0.50    0.05    --  -91.75 -29.00 -28.14   50
 89  ω   -106.00 -80.00   0.50    0.05    --  -91.75 -29.00 -15.51   52
 90  ω   -109.00 -83.00   0.50    0.05    --  -91.75 -26.00 -96.16   52
 91  ω   -111.00 -79.00   0.50    0.05    --  -91.75 -27.00-117.65   64
 92  ω   -106.00 -80.00   0.50    0.05    --  -91.75 -29.00-177.71   52
 93  ω   -152.00-110.00   0.50    0.05    --  -91.75-125.00   0.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1130773000
_diffrn_orient_matrix_UB_12      -0.0328097000
_diffrn_orient_matrix_UB_13      0.0243331000
_diffrn_orient_matrix_UB_21      -0.0157067000
_diffrn_orient_matrix_UB_22      -0.2233069000
_diffrn_orient_matrix_UB_23      -0.0450269000
_diffrn_orient_matrix_UB_31      0.0019822000
_diffrn_orient_matrix_UB_32      0.1029641000
_diffrn_orient_matrix_UB_33      -0.0898337000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           1
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2690
_reflns_number_total             2808
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0066(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2808
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      1.088
_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)+(0.0412P)²+0.5829P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0959
_refine_ls_wR_factor_ref         0.0967
_refine_special_details          
;
The structure was refined by Least Squares SHELXL incorporated 
in Olex2 software program. All non-hydrogen atoms were refined anisotropically. 
Hydrogen atom positions were calculated geometrically and refined using the 
riding model, except for the hydrogen atom on the non-carbon atom(s) which were found 
by difference Fourier methods and refined isotropically when data permits.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.70274(7) 0.17089(17) 0.49194(7) 0.0156(2) Uani 1 1 d . . . . .
H1 H 0.720366 0.023469 0.475484 0.019 Uiso 1 1 calc R U . . .
C2 C 0.79090(7) 0.33358(16) 0.49749(7) 0.0148(2) Uani 1 1 d . . . . .
C3 C 0.80693(7) 0.43569(17) 0.59323(7) 0.0170(2) Uani 1 1 d . . . . .
C4 C 0.71204(8) 0.55818(18) 0.59680(7) 0.0202(2) Uani 1 1 d . . . . .
H4A H 0.687177 0.648673 0.542633 0.024 Uiso 1 1 calc R U . . .
H4B H 0.725480 0.651512 0.650603 0.024 Uiso 1 1 calc R U . . .
C5 C 0.63518(8) 0.37970(18) 0.60097(8) 0.0209(2) Uani 1 1 d . . . . .
H5A H 0.620443 0.380144 0.659817 0.025 Uiso 1 1 calc R U . . .
H5B H 0.572663 0.399282 0.552759 0.025 Uiso 1 1 calc R U . . .
C6 C 0.68772(7) 0.17116(17) 0.58743(7) 0.0161(2) Uani 1 1 d . . . . .
H6 H 0.660086 0.035550 0.605574 0.019 Uiso 1 1 calc R U . . .
C7 C 0.79250(7) 0.22897(17) 0.64192(7) 0.0168(2) Uani 1 1 d . . . . .
C8 C 0.64928(7) 0.42694(17) 0.37790(7) 0.0161(2) Uani 1 1 d . . . . .
C9 C 0.59338(8) 0.54015(18) 0.30342(7) 0.0192(2) Uani 1 1 d . . . . .
H9 H 0.526411 0.502615 0.275151 0.023 Uiso 1 1 calc R U . . .
C10 C 0.63906(8) 0.71065(18) 0.27170(7) 0.0205(2) Uani 1 1 d . . . . .
H10 H 0.601944 0.790641 0.221327 0.025 Uiso 1 1 calc R U . . .
C11 C 0.73699(8) 0.76666(17) 0.31157(7) 0.0198(2) Uani 1 1 d . . . . .
H11 H 0.766330 0.882980 0.288446 0.024 Uiso 1 1 calc R U . . .
C12 C 0.79233(8) 0.65064(17) 0.38611(7) 0.0174(2) Uani 1 1 d . . . . .
H12 H 0.859630 0.686854 0.413604 0.021 Uiso 1 1 calc R U . . .
C13 C 0.74832(7) 0.48312(17) 0.41936(7) 0.0149(2) Uani 1 1 d . . . . .
C14 C 0.53197(8) 0.13123(19) 0.38691(8) 0.0231(2) Uani 1 1 d . . . . .
H14A H 0.486278 0.209353 0.337547 0.035 Uiso 1 1 calc R U . . .
H14B H 0.499875 0.104508 0.434516 0.035 Uiso 1 1 calc R U . . .
H14C H 0.549819 -0.006391 0.364679 0.035 Uiso 1 1 calc R U . . .
C15 C 0.88406(8) 0.21788(18) 0.48873(7) 0.0199(2) Uani 1 1 d . . . . .
H15A H 0.867890 0.133811 0.433056 0.030 Uiso 1 1 calc R U . . .
H15B H 0.908772 0.121434 0.540115 0.030 Uiso 1 1 calc R U . . .
H15C H 0.935106 0.324373 0.487422 0.030 Uiso 1 1 calc R U . . .
C16 C 0.90273(9) 0.5568(2) 0.63189(8) 0.0254(3) Uani 1 1 d . . . . .
H16A H 0.958946 0.459847 0.636501 0.038 Uiso 1 1 calc R U . . .
H16B H 0.904612 0.611205 0.691681 0.038 Uiso 1 1 calc R U . . .
H16C H 0.906700 0.677958 0.592521 0.038 Uiso 1 1 calc R U . . .
N1 N 0.61990(7) 0.25769(16) 0.42211(6) 0.0219(2) Uani 1 1 d . . . . .
O1 O 0.84837(6) 0.13875(14) 0.70476(5) 0.0253(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 1.0000 . ?
C1 C2 1.5823(14) . ?
C1 C6 1.5523(14) . ?
C1 N1 1.4551(13) . ?
C2 C3 1.5718(14) . ?
C2 C13 1.5117(14) . ?
C2 C15 1.5318(14) . ?
C3 C4 1.5491(15) . ?
C3 C7 1.5313(14) . ?
C3 C16 1.5129(14) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.5615(15) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.5339(15) . ?
C6 H6 1.0000 . ?
C6 C7 1.5227(14) . ?
C7 O1 1.2060(13) . ?
C8 C9 1.3931(15) . ?
C8 C13 1.4051(14) . ?
C8 N1 1.3794(14) . ?
C9 H9 0.9500 . ?
C9 C10 1.3966(16) . ?
C10 H10 0.9500 . ?
C10 C11 1.3870(16) . ?
C11 H11 0.9500 . ?
C11 C12 1.4000(15) . ?
C12 H12 0.9500 . ?
C12 C13 1.3812(14) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C14 N1 1.4374(13) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
C2 C1 H1 110.7 . . ?
C6 C1 H1 110.7 . . ?
C6 C1 C2 105.02(8) . . ?
N1 C1 H1 110.7 . . ?
N1 C1 C2 104.84(8) . . ?
N1 C1 C6 114.63(8) . . ?
C3 C2 C1 102.34(8) . . ?
C13 C2 C1 102.66(8) . . ?
C13 C2 C3 115.45(8) . . ?
C13 C2 C15 112.02(8) . . ?
C15 C2 C1 111.76(8) . . ?
C15 C2 C3 111.79(8) . . ?
C4 C3 C2 109.44(8) . . ?
C7 C3 C2 97.08(8) . . ?
C7 C3 C4 99.28(8) . . ?
C16 C3 C2 116.94(9) . . ?
C16 C3 C4 114.92(9) . . ?
C16 C3 C7 116.54(9) . . ?
C3 C4 H4A 110.7 . . ?
C3 C4 H4B 110.7 . . ?
C3 C4 C5 105.35(8) . . ?
H4A C4 H4B 108.8 . . ?
C5 C4 H4A 110.7 . . ?
C5 C4 H4B 110.7 . . ?
C4 C5 H5A 111.1 . . ?
C4 C5 H5B 111.1 . . ?
H5A C5 H5B 109.1 . . ?
C6 C5 C4 103.25(8) . . ?
C6 C5 H5A 111.1 . . ?
C6 C5 H5B 111.1 . . ?
C1 C6 H6 115.7 . . ?
C5 C6 C1 109.23(8) . . ?
C5 C6 H6 115.7 . . ?
C7 C6 C1 99.38(8) . . ?
C7 C6 C5 98.79(8) . . ?
C7 C6 H6 115.7 . . ?
C6 C7 C3 99.45(8) . . ?
O1 C7 C3 129.96(10) . . ?
O1 C7 C6 130.59(10) . . ?
C9 C8 C13 120.84(10) . . ?
N1 C8 C9 128.23(10) . . ?
N1 C8 C13 110.92(9) . . ?
C8 C9 H9 121.1 . . ?
C8 C9 C10 117.78(10) . . ?
C10 C9 H9 121.1 . . ?
C9 C10 H10 119.0 . . ?
C11 C10 C9 121.96(10) . . ?
C11 C10 H10 119.0 . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.56(10) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 H12 120.3 . . ?
C13 C12 C11 119.50(10) . . ?
C13 C12 H12 120.3 . . ?
C8 C13 C2 109.58(9) . . ?
C12 C13 C2 130.05(9) . . ?
C12 C13 C8 120.36(9) . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
C2 C15 H15A 109.5 . . ?
C2 C15 H15B 109.5 . . ?
C2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C3 C16 H16A 109.5 . . ?
C3 C16 H16B 109.5 . . ?
C3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C8 N1 C1 111.35(8) . . ?
C8 N1 C14 124.90(9) . . ?
C14 N1 C1 120.36(9) . . ?

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 -62.60(10) . . . . ?
C1 C2 C3 C7 39.88(9) . . . . ?
C1 C2 C3 C16 164.51(9) . . . . ?
C1 C2 C13 C8 3.22(11) . . . . ?
C1 C2 C13 C12 -175.46(10) . . . . ?
C1 C6 C7 C3 54.32(9) . . . . ?
C1 C6 C7 O1 -125.35(12) . . . . ?
C2 C1 C6 C5 75.20(10) . . . . ?
C2 C1 C6 C7 -27.60(10) . . . . ?
C2 C1 N1 C8 8.31(11) . . . . ?
C2 C1 N1 C14 168.52(9) . . . . ?
C2 C3 C4 C5 73.73(10) . . . . ?
C2 C3 C7 C6 -59.13(9) . . . . ?
C2 C3 C7 O1 120.54(12) . . . . ?
C3 C2 C13 C8 -107.24(10) . . . . ?
C3 C2 C13 C12 74.09(14) . . . . ?
C3 C4 C5 C6 -6.90(10) . . . . ?
C4 C3 C7 C6 51.98(9) . . . . ?
C4 C3 C7 O1 -128.35(12) . . . . ?
C4 C5 C6 C1 -64.68(10) . . . . ?
C4 C5 C6 C7 38.53(9) . . . . ?
C5 C6 C7 C3 -56.99(9) . . . . ?
C5 C6 C7 O1 123.34(12) . . . . ?
C6 C1 C2 C3 -7.86(10) . . . . ?
C6 C1 C2 C13 -127.86(8) . . . . ?
C6 C1 C2 C15 111.91(9) . . . . ?
C6 C1 N1 C8 122.91(10) . . . . ?
C6 C1 N1 C14 -76.88(13) . . . . ?
C7 C3 C4 C5 -27.23(10) . . . . ?
C8 C9 C10 C11 0.59(16) . . . . ?
C9 C8 C13 C2 -179.59(9) . . . . ?
C9 C8 C13 C12 -0.77(15) . . . . ?
C9 C8 N1 C1 174.86(10) . . . . ?
C9 C8 N1 C14 15.73(18) . . . . ?
C9 C10 C11 C12 -0.29(16) . . . . ?
C10 C11 C12 C13 -0.54(16) . . . . ?
C11 C12 C13 C2 179.62(10) . . . . ?
C11 C12 C13 C8 1.06(15) . . . . ?
C13 C2 C3 C4 48.05(11) . . . . ?
C13 C2 C3 C7 150.53(8) . . . . ?
C13 C2 C3 C16 -84.84(11) . . . . ?
C13 C8 C9 C10 -0.06(15) . . . . ?
C13 C8 N1 C1 -6.62(12) . . . . ?
C13 C8 N1 C14 -165.75(10) . . . . ?
C15 C2 C3 C4 177.65(8) . . . . ?
C15 C2 C3 C7 -79.86(9) . . . . ?
C15 C2 C3 C16 44.77(12) . . . . ?
C15 C2 C13 C8 123.27(9) . . . . ?
C15 C2 C13 C12 -55.41(14) . . . . ?
C16 C3 C4 C5 -152.34(9) . . . . ?
C16 C3 C7 C6 175.94(9) . . . . ?
C16 C3 C7 O1 -4.38(17) . . . . ?
N1 C1 C2 C3 113.30(9) . . . . ?
N1 C1 C2 C13 -6.70(10) . . . . ?
N1 C1 C2 C15 -126.93(9) . . . . ?
N1 C1 C6 C5 -39.30(12) . . . . ?
N1 C1 C6 C7 -142.10(9) . . . . ?
N1 C8 C9 C10 178.33(10) . . . . ?
N1 C8 C13 C2 1.76(12) . . . . ?
N1 C8 C13 C12 -179.42(9) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id ZTP-4-33
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.207
_oxdiff_exptl_absorpt_empirical_full_min 0.782
