# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_liumeiling_0610_auto
_database_code_depnum_ccdc_archive 'CCDC 2120476'
loop_
_audit_author_name
_audit_author_address
'meiling liu'
;Lanzhou University
China
;
_audit_update_record             
;
2021-11-06 deposited with the CCDC.	2022-03-07 downloaded from the CCDC.
;
_audit_creation_date             2021-06-10
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H24 N2 O2'
_chemical_formula_sum            'C23 H24 N2 O2'
_chemical_formula_weight         360.44
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   15.2395(2)
_cell_length_b                   7.74000(10)
_cell_length_c                   17.5038(2)
_cell_angle_alpha                90
_cell_angle_beta                 114.5730(10)
_cell_angle_gamma                90
_cell_volume                     1877.65(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10006
_cell_measurement_temperature    299.53(10)
_cell_measurement_theta_max      77.2090
_cell_measurement_theta_min      2.7670
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.647
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84560
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.103a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0149
_diffrn_reflns_av_unetI/netI     0.0129
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12858
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.351
_diffrn_reflns_theta_min         3.242
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299.53(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     36.00 122.00   0.50    0.05    --   47.57  13.00 -29.00  172
  2  ω    109.00 174.00   0.50    0.05    --  107.75  37.00-120.00  130
  3  ω     94.00 155.00   0.50    0.05    --  107.75  13.00 -29.00  122
  4  ω    150.00 175.00   0.50    0.05    --  107.75  19.00  60.00   50
  5  ω    103.00 136.00   0.50    0.05    --  107.75  19.00  60.00   66
  6  ω     78.00 104.00   0.50    0.05    --  107.75 -99.00  90.00   52
  7  ω     38.00  97.00   0.50    0.05    --  107.75 -99.00   0.00  118
  8  ω    -45.00  24.00   0.50    0.05    --  -47.57  37.00  90.00  138
  9  ω    -26.00  15.00   0.50    0.05    --  -47.57  13.00 -29.00   82
 10  ω    -26.00  -1.00   0.50    0.05    --   47.57 -13.00 159.00   50
 11  ω     36.00  61.00   0.50    0.05    --  107.75 -57.00 150.00   50
 12  ω     38.00  63.00   0.50    0.05    --  107.75 -57.00  30.00   50
 13  ω     36.00  62.00   0.50    0.05    --  107.75 -57.00   0.00   52
 14  ω     37.00  62.00   0.50    0.05    --  107.75 -57.00-150.00   50
 15  ω   -122.00 -63.00   0.50    0.05    --  -47.57 -13.00 159.00  118
 16  ω   -150.00 -87.00   0.50    0.05    -- -100.00 -13.00 159.00  126
 17  ω    -66.00 -30.00   0.50    0.05    -- -100.00  57.00 120.00   72
 18  ω    -66.00 -37.00   0.50    0.05    -- -100.00  57.00 150.00   58
 19  ω   -109.00 -75.00   0.50    0.05    -- -100.00  77.00 120.00   68
 20  ω    -69.00 -34.00   0.50    0.05    -- -100.00  57.00  60.00   70
 21  ω    -53.00 -27.00   0.50    0.05    -- -100.00  57.00-120.00   52
 22  ω    -69.00 -28.00   0.50    0.05    -- -100.00  57.00-180.00   82
 23  ω    -95.00 -70.00   0.50    0.05    --  -47.57 125.00-150.00   50
 24  ω    -65.00 -26.00   0.50    0.05    --  -47.57 125.00-150.00   78
 25  ω   -112.00 -59.00   0.50    0.05    -- -100.00 125.00  60.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1027761000
_diffrn_orient_matrix_UB_12      0.0147439000
_diffrn_orient_matrix_UB_13      0.0700749000
_diffrn_orient_matrix_UB_21      0.0399330000
_diffrn_orient_matrix_UB_22      0.0309104000
_diffrn_orient_matrix_UB_23      -0.0665177000
_diffrn_orient_matrix_UB_31      -0.0140629000
_diffrn_orient_matrix_UB_32      0.1961029000
_diffrn_orient_matrix_UB_33      0.0052526000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\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                3501
_reflns_number_total             3739
_reflns_odcompleteness_completeness 98.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.103a (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3739
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0403
_refine_ls_restrained_S_all      1.035
_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)+(0.0587P)²+0.3556P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1113
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C19(H19B,H19A), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C14(H14), C15(H15), C16(H16), C17(H17)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), 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 0.41057(6) 0.59848(13) 0.54552(5) 0.0548(2) Uani 1 1 d . . . . .
O2 O 0.45537(7) -0.11495(11) 0.70598(6) 0.0562(2) Uani 1 1 d . . . . .
N1 N 0.38888(7) 0.50485(12) 0.65855(6) 0.0383(2) Uani 1 1 d . . . . .
N2 N 0.52127(7) 0.20640(12) 0.67365(6) 0.0417(2) Uani 1 1 d . . . . .
C1 C 0.29051(8) 0.46438(15) 0.61931(8) 0.0431(3) Uani 1 1 d . . . . .
C2 C 0.22573(10) 0.47136(19) 0.53557(9) 0.0575(3) Uani 1 1 d . . . . .
H2 H 0.243966 0.511672 0.494251 0.069 Uiso 1 1 calc R . . . .
C3 C 0.13254(11) 0.4154(2) 0.51636(11) 0.0725(4) Uani 1 1 d . . . . .
H3 H 0.087277 0.418015 0.460762 0.087 Uiso 1 1 calc R . . . .
C4 C 0.10497(10) 0.3558(2) 0.57774(12) 0.0719(4) Uani 1 1 d . . . . .
H4 H 0.041696 0.319670 0.562491 0.086 Uiso 1 1 calc R . . . .
C5 C 0.16910(10) 0.34887(18) 0.66048(10) 0.0596(4) Uani 1 1 d . . . . .
H5 H 0.149872 0.308864 0.701246 0.072 Uiso 1 1 calc R . . . .
C6 C 0.26432(8) 0.40337(15) 0.68244(8) 0.0455(3) Uani 1 1 d . . . . .
C7 C 0.34768(9) 0.40955(15) 0.76120(7) 0.0439(3) Uani 1 1 d . . . . .
C8 C 0.42267(8) 0.47095(14) 0.74542(7) 0.0386(2) Uani 1 1 d . . . . .
C9 C 0.34674(11) 0.3537(2) 0.84298(9) 0.0613(4) Uani 1 1 d . . . . .
H9A H 0.402397 0.283586 0.873302 0.092 Uiso 1 1 calc GR . . . .
H9B H 0.289313 0.288153 0.832153 0.092 Uiso 1 1 calc GR . . . .
H9C H 0.347906 0.453810 0.875798 0.092 Uiso 1 1 calc GR . . . .
C10 C 0.44645(8) 0.55201(14) 0.61834(7) 0.0388(2) Uani 1 1 d . . . . .
C11 C 0.55426(8) 0.52435(14) 0.66705(7) 0.0386(2) Uani 1 1 d . . . . .
C12 C 0.58702(8) 0.54271(15) 0.76108(7) 0.0409(3) Uani 1 1 d . . . . .
C13 C 0.52323(8) 0.50993(15) 0.79860(7) 0.0417(3) Uani 1 1 d . . . . .
C14 C 0.55784(11) 0.5214(2) 0.88591(8) 0.0616(4) Uani 1 1 d . . . . .
H14 H 0.516053 0.501054 0.911358 0.074 Uiso 1 1 calc R . . . .
C15 C 0.65254(12) 0.5624(3) 0.93489(9) 0.0822(5) Uani 1 1 d . . . . .
H15 H 0.674204 0.569247 0.992931 0.099 Uiso 1 1 calc R . . . .
C16 C 0.71535(12) 0.5932(3) 0.89837(10) 0.0798(5) Uani 1 1 d . . . . .
H16 H 0.779497 0.620596 0.931424 0.096 Uiso 1 1 calc R . . . .
C17 C 0.68232(10) 0.5831(2) 0.81248(9) 0.0593(4) Uani 1 1 d . . . . .
H17 H 0.725075 0.603913 0.788057 0.071 Uiso 1 1 calc R . . . .
C18 C 0.60839(9) 0.64284(17) 0.63092(8) 0.0503(3) Uani 1 1 d . . . . .
H18A H 0.578979 0.635892 0.570711 0.076 Uiso 1 1 calc GR . . . .
H18B H 0.674550 0.606934 0.651477 0.076 Uiso 1 1 calc GR . . . .
H18C H 0.605494 0.759803 0.647975 0.076 Uiso 1 1 calc GR . . . .
C19 C 0.57289(9) 0.33393(15) 0.64733(8) 0.0455(3) Uani 1 1 d . . . . .
H19B H 0.553785 0.322560 0.587342 0.055 Uiso 1 1 calc R . . . .
H19A H 0.641495 0.310147 0.675294 0.055 Uiso 1 1 calc R . . . .
C20 C 0.58187(9) 0.09944(16) 0.74434(8) 0.0479(3) Uani 1 1 d . . . . .
H20A H 0.623189 0.172374 0.790293 0.058 Uiso 1 1 calc R . . . .
H20B H 0.622628 0.026148 0.727801 0.058 Uiso 1 1 calc R . . . .
C21 C 0.51945(11) -0.01066(17) 0.77263(8) 0.0545(3) Uani 1 1 d . . . . .
H21A H 0.560138 -0.084224 0.818588 0.065 Uiso 1 1 calc R . . . .
H21B H 0.482460 0.063196 0.793098 0.065 Uiso 1 1 calc R . . . .
C22 C 0.39508(10) -0.00911(18) 0.63817(10) 0.0582(3) Uani 1 1 d . . . . .
H22A H 0.356454 0.064983 0.656774 0.070 Uiso 1 1 calc R . . . .
H22B H 0.351559 -0.081496 0.593099 0.070 Uiso 1 1 calc R . . . .
C23 C 0.45398(10) 0.10065(17) 0.60579(8) 0.0526(3) Uani 1 1 d . . . . .
H23A H 0.489326 0.027093 0.583516 0.063 Uiso 1 1 calc R . . . .
H23B H 0.411576 0.174375 0.560760 0.063 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 C10 1.2137(13) . ?
O2 C21 1.4208(16) . ?
O2 C22 1.4202(16) . ?
N1 C1 1.4002(15) . ?
N1 C8 1.4124(14) . ?
N1 C10 1.3829(13) . ?
N2 C19 1.4514(15) . ?
N2 C20 1.4556(15) . ?
N2 C23 1.4558(15) . ?
C1 C2 1.3866(18) . ?
C1 C6 1.4036(17) . ?
C2 C3 1.386(2) . ?
C3 C4 1.385(2) . ?
C4 C5 1.371(2) . ?
C5 C6 1.4026(17) . ?
C6 C7 1.4354(18) . ?
C7 C8 1.3676(15) . ?
C7 C9 1.5010(16) . ?
C8 C13 1.4559(16) . ?
C10 C11 1.5189(16) . ?
C11 C12 1.5150(15) . ?
C11 C18 1.5346(15) . ?
C11 C19 1.5664(15) . ?
C12 C13 1.4042(15) . ?
C12 C17 1.3892(17) . ?
C13 C14 1.3969(17) . ?
C14 C15 1.374(2) . ?
C15 C16 1.375(2) . ?
C16 C17 1.375(2) . ?
C20 C21 1.5061(18) . ?
C22 C23 1.507(2) . ?

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
C22 O2 C21 110.09(10) . . ?
C1 N1 C8 108.86(9) . . ?
C10 N1 C1 125.86(9) . . ?
C10 N1 C8 124.93(9) . . ?
C19 N2 C20 114.87(10) . . ?
C19 N2 C23 114.48(10) . . ?
C20 N2 C23 110.88(9) . . ?
N1 C1 C6 106.62(10) . . ?
C2 C1 N1 131.01(11) . . ?
C2 C1 C6 122.33(12) . . ?
C3 C2 C1 116.85(14) . . ?
C4 C3 C2 121.78(15) . . ?
C5 C4 C3 121.29(13) . . ?
C4 C5 C6 118.67(14) . . ?
C1 C6 C7 108.48(10) . . ?
C5 C6 C1 119.07(12) . . ?
C5 C6 C7 132.44(12) . . ?
C6 C7 C9 123.42(11) . . ?
C8 C7 C6 107.32(10) . . ?
C8 C7 C9 129.25(12) . . ?
N1 C8 C13 117.74(9) . . ?
C7 C8 N1 108.71(10) . . ?
C7 C8 C13 133.52(10) . . ?
O1 C10 N1 120.58(10) . . ?
O1 C10 C11 122.75(10) . . ?
N1 C10 C11 116.37(9) . . ?
C10 C11 C18 109.01(9) . . ?
C10 C11 C19 105.18(9) . . ?
C12 C11 C10 112.80(9) . . ?
C12 C11 C18 113.63(10) . . ?
C12 C11 C19 108.63(9) . . ?
C18 C11 C19 107.08(9) . . ?
C13 C12 C11 120.78(10) . . ?
C17 C12 C11 120.54(10) . . ?
C17 C12 C13 118.59(11) . . ?
C12 C13 C8 119.20(10) . . ?
C14 C13 C8 122.07(11) . . ?
C14 C13 C12 118.70(11) . . ?
C15 C14 C13 121.21(13) . . ?
C14 C15 C16 120.22(13) . . ?
C17 C16 C15 119.30(14) . . ?
C16 C17 C12 121.98(13) . . ?
N2 C19 C11 113.47(9) . . ?
N2 C20 C21 109.70(10) . . ?
O2 C21 C20 111.34(11) . . ?
O2 C22 C23 111.09(11) . . ?
N2 C23 C22 109.74(11) . . ?

_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 1.458
_oxdiff_exptl_absorpt_empirical_full_min 0.598
