# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

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

data_KGardner01_Sarpong
_database_code_depnum_ccdc_archive 'CCDC 2339055'
loop_
_audit_author_name
_audit_author_address
' Nick Settineri'
;University of California, Berkeley
United States of America
;
_audit_update_record             
;
2024-03-09 deposited with the CCDC.	2024-08-30 downloaded from the CCDC.
;
_audit_creation_date             2021-06-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H21 N O'
_chemical_formula_sum            'C22 H21 N O'
_chemical_formula_weight         315.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C N O H'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.86970(10)
_cell_length_b                   14.3822(2)
_cell_length_c                   9.93520(10)
_cell_angle_alpha                90
_cell_angle_beta                 95.7760(10)
_cell_angle_gamma                90
_cell_volume                     1687.45(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13503
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.1270
_cell_measurement_theta_min      4.8150
_shelx_estimated_absorpt_T_max   0.938
_shelx_estimated_absorpt_T_min   0.858
_exptl_absorpt_coefficient_mu    0.585
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74274
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.109a (Rigaku Oxford Diffraction, 2021)
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    1.241
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            19025
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.445
_diffrn_reflns_theta_min         3.743
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     37.00  63.00   0.50    0.50    --   50.96  57.00-120.00   52
  2  ω     91.00 125.00   0.50    0.50    --   50.96  77.00-180.00   68
  3  ω    107.00 163.00   0.50    0.50    --  107.75  61.00-180.00  112
  4  ω     39.00  97.00   0.50    0.50    --  107.75 -77.00 -90.00  116
  5  ω     40.00  88.00   0.50    0.50    --  107.75 -77.00  30.00   96
  6  ω     36.00  68.00   0.50    0.50    --  107.75 -61.00  60.00   64
  7  ω     40.00  68.00   0.50    0.50    --  107.75 -61.00  90.00   56
  8  ω     36.00  66.00   0.50    0.50    --  107.75 -61.00 150.00   60
  9  ω     39.00  67.00   0.50    0.50    --  107.75 -61.00 -90.00   56
 10  ω     41.00  67.00   0.50    0.50    --  107.75 -61.00-180.00   52
 11  ω     65.00  90.00   0.50    0.50    --  107.75-169.00-148.00   50
 12  ω     74.00 100.00   0.50    0.50    --  107.75-111.00-150.00   52
 13  ω     31.00  56.00   0.50    0.50    --  107.75-111.00-150.00   50
 14  ω     10.00  94.00   0.50    0.50    --   50.96-115.00  -4.00  168
 15  ω     70.00  95.00   0.50    0.50    --  107.75-115.00  -4.00   50
 16  ω     77.00 104.00   0.50    0.50    --  107.75 -94.00 -60.00   54
 17  ω     74.00 100.00   0.50    0.50    --  107.75 -94.00   0.00   52
 18  ω     73.00 106.00   0.50    0.50    --  107.75 -94.00  30.00   66
 19  ω     33.00  59.00   0.50    0.50    --  107.75 -94.00   0.00   52
 20  ω     75.00 109.00   0.50    0.50    --  107.75-111.00 150.00   68
 21  ω   -124.00 -82.00   0.50    0.50    --  -50.96 -77.00  30.00   84
 22  ω   -173.00 -88.00   0.50    0.50    -- -100.00 -94.00 -30.00  170
 23  ω    -70.00 -45.00   0.50    0.50    -- -100.00  61.00 150.00   50
 24  ω    -52.00 -26.00   0.50    0.50    -- -100.00  45.00  30.00   52
 25  ω    -52.00 -26.00   0.50    0.50    -- -100.00  45.00 -90.00   52
 26  ω    -54.00 -29.00   0.50    0.50    -- -100.00  45.00-150.00   50
 27  ω    -52.00 -26.00   0.50    0.50    -- -100.00  45.00-180.00   52
 28  ω    -54.00 -25.00   0.50    0.50    -- -100.00  45.00-120.00   58
 29  ω    -53.00 -26.00   0.50    0.50    -- -100.00  45.00 -60.00   54
 30  ω    -43.00  12.00   0.50    0.50    --  -50.96  38.00   0.00  110
 31  ω    -51.00 -26.00   0.50    0.50    -- -100.00  45.00  60.00   50
 32  ω    -46.00  24.00   0.50    0.50    --  -50.96  38.00 120.00  140
 33  ω    -94.00 -16.00   0.50    0.50    --  -50.96 115.00  85.00  156
 34  ω   -110.00 -23.00   0.50    0.50    -- -100.00 115.00  85.00  174
 35  ω    -89.00 -53.00   0.50    0.50    --  -50.96 125.00-180.00   72
 36  ω     46.00 128.00   0.50    0.50    --   50.96 169.00-130.00  164
 37  ω     55.00 105.00   0.50    0.50    --  107.75 169.00-130.00  100
 38  ω     81.00 149.00   0.50    0.50    --  107.75 115.00  85.00  136
 39  ω     81.00 127.00   0.50    0.50    --   50.96 115.00  85.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0059027000
_diffrn_orient_matrix_UB_12      0.0803415000
_diffrn_orient_matrix_UB_13      0.1016263000
_diffrn_orient_matrix_UB_21      -0.0252350000
_diffrn_orient_matrix_UB_22      0.0687423000
_diffrn_orient_matrix_UB_23      -0.1180677000
_diffrn_orient_matrix_UB_31      -0.1278573000
_diffrn_orient_matrix_UB_32      -0.0172639000
_diffrn_orient_matrix_UB_33      0.0027109000
_diffrn_oxdiff_digest_frames     
;
0189b980bc9559715e807078e2184b5b7d03210be3c
;
_diffrn_oxdiff_digest_hkl        
;
01b7986a3cfb7ba85273612beffaa35ede63c6
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3240
_reflns_number_total             3443
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.41.109a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.109a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.109a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3443
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0384
_refine_ls_restrained_S_all      1.029
_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)+(0.0489P)²+0.6659P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.0983
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
;
_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 0.13676(7) 0.26054(6) 0.68236(8) 0.0265(2) Uani 1 1 d . . . . .
N1 N 0.29850(7) 0.30829(6) 0.50345(9) 0.0180(2) Uani 1 1 d . . . . .
C1 C 0.28657(9) 0.36493(8) 0.62389(11) 0.0206(2) Uani 1 1 d . . . . .
H1A H 0.3032 0.4309 0.6052 0.025 Uiso 1 1 calc R . . . .
H1B H 0.3407 0.3435 0.6999 0.025 Uiso 1 1 calc R . . . .
C2 C 0.16626(9) 0.35563(8) 0.66118(12) 0.0244(2) Uani 1 1 d . . . . .
H2A H 0.1583 0.3916 0.7447 0.029 Uiso 1 1 calc R . . . .
H2B H 0.1133 0.3822 0.5878 0.029 Uiso 1 1 calc R . . . .
C3 C 0.15084(10) 0.20702(8) 0.56402(12) 0.0255(3) Uani 1 1 d . . . . .
H3A H 0.0995 0.2311 0.4872 0.031 Uiso 1 1 calc R . . . .
H3B H 0.1300 0.1415 0.5796 0.031 Uiso 1 1 calc R . . . .
C4 C 0.27202(9) 0.21125(8) 0.52859(11) 0.0213(2) Uani 1 1 d . . . . .
H4A H 0.3242 0.1865 0.6042 0.026 Uiso 1 1 calc R . . . .
H4B H 0.2805 0.1734 0.4470 0.026 Uiso 1 1 calc R . . . .
C5 C 0.39216(8) 0.32782(7) 0.43096(10) 0.0170(2) Uani 1 1 d . . . . .
C6 C 0.39765(8) 0.41417(7) 0.36400(10) 0.0170(2) Uani 1 1 d . . . . .
C7 C 0.30620(8) 0.48548(7) 0.36160(10) 0.0171(2) Uani 1 1 d . . . . .
C8 C 0.19177(9) 0.46145(8) 0.33269(11) 0.0190(2) Uani 1 1 d . . . . .
H8 H 0.1710 0.3981 0.3191 0.023 Uiso 1 1 calc R . . . .
C9 C 0.10871(9) 0.52968(8) 0.32379(11) 0.0220(2) Uani 1 1 d . . . . .
H9 H 0.0315 0.5127 0.3034 0.026 Uiso 1 1 calc R . . . .
C10 C 0.13741(9) 0.62274(8) 0.34447(12) 0.0222(2) Uani 1 1 d . . . . .
H10 H 0.0803 0.6693 0.3377 0.027 Uiso 1 1 calc R . . . .
C11 C 0.25027(9) 0.64694(8) 0.37506(11) 0.0208(2) Uani 1 1 d . . . . .
H11 H 0.2705 0.7102 0.3908 0.025 Uiso 1 1 calc R . . . .
C12 C 0.33393(9) 0.57882(8) 0.38281(11) 0.0188(2) Uani 1 1 d . . . . .
H12 H 0.4110 0.5962 0.4028 0.023 Uiso 1 1 calc R . . . .
C13 C 0.49092(8) 0.43266(7) 0.29318(10) 0.0179(2) Uani 1 1 d . . . . .
H13 H 0.4951 0.4911 0.2494 0.021 Uiso 1 1 calc R . . . .
C14 C 0.57842(9) 0.36857(7) 0.28422(11) 0.0184(2) Uani 1 1 d . . . . .
C15 C 0.67632(9) 0.39046(7) 0.20755(11) 0.0189(2) Uani 1 1 d . . . . .
C16 C 0.66115(9) 0.43447(8) 0.08168(12) 0.0228(2) Uani 1 1 d . . . . .
H16 H 0.5876 0.4545 0.0472 0.027 Uiso 1 1 calc R . . . .
C17 C 0.75191(10) 0.44941(9) 0.00607(12) 0.0268(3) Uani 1 1 d . . . . .
H17 H 0.7401 0.4791 -0.0796 0.032 Uiso 1 1 calc R . . . .
C18 C 0.85998(10) 0.42090(9) 0.05597(12) 0.0264(3) Uani 1 1 d . . . . .
H18 H 0.9220 0.4303 0.0041 0.032 Uiso 1 1 calc R . . . .
C19 C 0.87684(9) 0.37857(8) 0.18192(12) 0.0234(2) Uani 1 1 d . . . . .
H19 H 0.9507 0.3595 0.2166 0.028 Uiso 1 1 calc R . . . .
C20 C 0.78612(9) 0.36396(8) 0.25761(11) 0.0206(2) Uani 1 1 d . . . . .
H20 H 0.7987 0.3357 0.3442 0.025 Uiso 1 1 calc R . . . .
C21 C 0.57009(9) 0.28271(8) 0.34774(11) 0.0196(2) Uani 1 1 d . . . . .
H21 H 0.6274 0.2372 0.3413 0.023 Uiso 1 1 calc R . . . .
C22 C 0.47870(9) 0.26300(7) 0.42046(11) 0.0192(2) Uani 1 1 d . . . . .
H22 H 0.4750 0.2044 0.4638 0.023 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.4325(14) . ?
O1 C3 1.4292(15) . ?
N1 C1 1.4661(14) . ?
N1 C4 1.4578(14) . ?
N1 C5 1.4124(13) . ?
C1 C2 1.5169(15) . ?
C3 C4 1.5161(15) . ?
C5 C6 1.4135(15) . ?
C5 C22 1.3988(15) . ?
C6 C7 1.4918(14) . ?
C6 C13 1.3958(14) . ?
C7 C8 1.4030(14) . ?
C7 C12 1.3930(15) . ?
C8 C9 1.3875(15) . ?
C9 C10 1.3912(16) . ?
C10 C11 1.3877(16) . ?
C11 C12 1.3915(15) . ?
C13 C14 1.3982(15) . ?
C14 C15 1.4859(14) . ?
C14 C21 1.3947(15) . ?
C15 C16 1.3969(16) . ?
C15 C20 1.4003(15) . ?
C16 C17 1.3907(16) . ?
C17 C18 1.3897(17) . ?
C18 C19 1.3879(17) . ?
C19 C20 1.3900(15) . ?
C21 C22 1.3917(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 C2 110.04(8) . . ?
C4 N1 C1 110.61(8) . . ?
C5 N1 C1 116.83(8) . . ?
C5 N1 C4 118.17(8) . . ?
N1 C1 C2 108.72(9) . . ?
O1 C2 C1 111.73(9) . . ?
O1 C3 C4 111.20(9) . . ?
N1 C4 C3 107.70(9) . . ?
N1 C5 C6 119.38(9) . . ?
C22 C5 N1 121.81(9) . . ?
C22 C5 C6 118.79(9) . . ?
C5 C6 C7 122.94(9) . . ?
C13 C6 C5 118.75(9) . . ?
C13 C6 C7 118.28(9) . . ?
C8 C7 C6 121.45(10) . . ?
C12 C7 C6 119.98(9) . . ?
C12 C7 C8 118.52(10) . . ?
C9 C8 C7 120.38(10) . . ?
C8 C9 C10 120.61(10) . . ?
C11 C10 C9 119.35(10) . . ?
C10 C11 C12 120.22(10) . . ?
C11 C12 C7 120.91(10) . . ?
C6 C13 C14 122.58(10) . . ?
C13 C14 C15 121.14(10) . . ?
C21 C14 C13 117.89(10) . . ?
C21 C14 C15 120.95(9) . . ?
C16 C15 C14 121.19(10) . . ?
C16 C15 C20 118.22(10) . . ?
C20 C15 C14 120.54(10) . . ?
C17 C16 C15 121.10(10) . . ?
C18 C17 C16 119.94(11) . . ?
C19 C18 C17 119.68(10) . . ?
C18 C19 C20 120.32(10) . . ?
C19 C20 C15 120.71(10) . . ?
C22 C21 C14 120.65(10) . . ?
C21 C22 C5 121.30(10) . . ?

_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 2.107
_oxdiff_exptl_absorpt_empirical_full_min 0.704
