# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
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data_2103027077
_database_code_depnum_ccdc_archive 'CCDC 2103666'
loop_
_audit_author_name
_audit_author_address
'Bingwei Zhou'
;Zhejiang University of Technology
China
;
_audit_update_record             
;
2021-08-17 deposited with the CCDC.	2021-10-12 downloaded from the CCDC.
;
_audit_creation_date             2021-03-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H19 N O2'
_chemical_formula_sum            'C20 H19 N O2'
_chemical_formula_weight         305.36
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0148 0.0070 '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 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   36.302(4)
_cell_length_b                   8.0420(10)
_cell_length_c                   5.3509(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1562.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9971
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      54.96
_cell_measurement_theta_min      7.52
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.971
_exptl_absorpt_coefficient_mu    0.427
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4755
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 19295 reflections, Rint = 0.2166
 (13309 with I > 3sig(I), Rint = 0.2072)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            9828
_diffrn_reflns_point_group_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.989
_diffrn_reflns_theta_min         4.238
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.705
_reflns_Friedel_fraction_full    0.892
_reflns_Friedel_fraction_max     0.880
_reflns_number_gt                2448
_reflns_number_total             2815
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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         0.137
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 877 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2815
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0576P)²+0.2303P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_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:
 C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C14(H14), C15(H15), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_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 0.29225(5) 0.8362(3) 0.0677(4) 0.0470(6) Uani 1 1 d . . . . .
O2 O 0.55094(5) 0.7045(3) 0.2423(4) 0.0409(6) Uani 1 1 d . . . . .
N1 N 0.30009(6) 0.6458(3) 0.3795(5) 0.0347(6) Uani 1 1 d . . . . .
C1 C 0.34236(7) 0.8795(4) 0.3526(6) 0.0324(7) Uani 1 1 d . . . . .
C2 C 0.37421(7) 0.9340(4) 0.1744(6) 0.0330(7) Uani 1 1 d . . . . .
H2A H 0.370876 0.899453 -0.001784 0.040 Uiso 1 1 calc R . . . .
H2B H 0.380935 1.053006 0.186965 0.040 Uiso 1 1 calc R . . . .
C3 C 0.39853(7) 0.8177(3) 0.3284(6) 0.0306(6) Uani 1 1 d . . . . .
C4 C 0.36994(7) 0.7634(4) 0.4691(6) 0.0309(6) Uani 1 1 d . . . . .
C5 C 0.35713(7) 0.6303(4) 0.6320(6) 0.0310(6) Uani 1 1 d . . . . .
C6 C 0.37647(7) 0.5569(4) 0.8275(6) 0.0355(7) Uani 1 1 d . . . . .
H6 H 0.400676 0.594262 0.864926 0.043 Uiso 1 1 calc R . . . .
C7 C 0.36110(9) 0.4303(4) 0.9685(7) 0.0418(8) Uani 1 1 d . . . . .
H7 H 0.374620 0.381360 1.101499 0.050 Uiso 1 1 calc R . . . .
C8 C 0.32590(8) 0.3758(4) 0.9140(7) 0.0445(8) Uani 1 1 d . . . . .
H8 H 0.315454 0.287747 1.008831 0.053 Uiso 1 1 calc R . . . .
C9 C 0.30558(8) 0.4479(4) 0.7226(6) 0.0409(8) Uani 1 1 d . . . . .
H9 H 0.281323 0.409878 0.688532 0.049 Uiso 1 1 calc R . . . .
C10 C 0.32073(7) 0.5761(4) 0.5802(6) 0.0327(7) Uani 1 1 d . . . . .
C11 C 0.31013(7) 0.7859(4) 0.2463(6) 0.0344(7) Uani 1 1 d . . . . .
C12 C 0.26489(8) 0.5682(4) 0.3125(8) 0.0484(9) Uani 1 1 d . . . . .
H12A H 0.268554 0.448663 0.286960 0.073 Uiso 1 1 calc GR . . . .
H12B H 0.255522 0.618332 0.158097 0.073 Uiso 1 1 calc GR . . . .
H12C H 0.247069 0.585716 0.447504 0.073 Uiso 1 1 calc GR . . . .
C13 C 0.43773(7) 0.7857(3) 0.3022(6) 0.0308(6) Uani 1 1 d . . . . .
C14 C 0.45773(7) 0.8618(4) 0.1109(6) 0.0349(7) Uani 1 1 d . . . . .
H14 H 0.445117 0.931401 -0.004264 0.042 Uiso 1 1 calc R . . . .
C15 C 0.49531(7) 0.8392(4) 0.0832(6) 0.0358(7) Uani 1 1 d . . . . .
H15 H 0.508204 0.893037 -0.048423 0.043 Uiso 1 1 calc R . . . .
C16 C 0.51394(7) 0.7373(4) 0.2495(6) 0.0330(7) Uani 1 1 d . . . . .
C17 C 0.49477(7) 0.6590(4) 0.4403(6) 0.0366(7) Uani 1 1 d . . . . .
H17 H 0.507543 0.588603 0.553557 0.044 Uiso 1 1 calc R . . . .
C18 C 0.45747(7) 0.6821(4) 0.4671(6) 0.0356(7) Uani 1 1 d . . . . .
H18 H 0.444796 0.627443 0.598922 0.043 Uiso 1 1 calc R . . . .
C19 C 0.57127(8) 0.7722(4) 0.0379(7) 0.0485(9) Uani 1 1 d . . . . .
H19A H 0.560200 0.735662 -0.119869 0.073 Uiso 1 1 calc GR . . . .
H19B H 0.596848 0.733650 0.046333 0.073 Uiso 1 1 calc GR . . . .
H19C H 0.570721 0.893934 0.046776 0.073 Uiso 1 1 calc GR . . . .
C20 C 0.32771(8) 1.0172(4) 0.5225(7) 0.0398(7) Uani 1 1 d . . . . .
H20A H 0.313172 0.967809 0.657864 0.060 Uiso 1 1 calc GR . . . .
H20B H 0.312126 1.092687 0.425114 0.060 Uiso 1 1 calc GR . . . .
H20C H 0.348429 1.079357 0.593600 0.060 Uiso 1 1 calc GR . . . .


_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 C11 1.224(4) . ?
O2 C16 1.370(3) . ?
O2 C19 1.428(4) . ?
N1 C10 1.424(4) . ?
N1 C11 1.382(4) . ?
N1 C12 1.467(4) . ?
C1 C2 1.562(4) . ?
C1 C4 1.504(4) . ?
C1 C11 1.503(4) . ?
C1 C20 1.528(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.528(4) . ?
C3 C4 1.355(4) . ?
C3 C13 1.453(4) . ?
C4 C5 1.456(4) . ?
C5 C6 1.392(4) . ?
C5 C10 1.419(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.384(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.382(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.389(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.394(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.396(4) . ?
C13 C18 1.410(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.384(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.386(4) . ?
C16 C17 1.387(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.374(4) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
C16 O2 C19 117.1(2) . . ?
C10 N1 C12 118.4(2) . . ?
C11 N1 C10 124.8(2) . . ?
C11 N1 C12 116.8(2) . . ?
C4 C1 C2 86.3(2) . . ?
C4 C1 C20 115.8(3) . . ?
C11 C1 C2 119.1(3) . . ?
C11 C1 C4 111.3(2) . . ?
C11 C1 C20 108.5(2) . . ?
C20 C1 C2 114.7(2) . . ?
C1 C2 H2A 114.4 . . ?
C1 C2 H2B 114.4 . . ?
H2A C2 H2B 111.5 . . ?
C3 C2 C1 85.8(2) . . ?
C3 C2 H2A 114.4 . . ?
C3 C2 H2B 114.4 . . ?
C4 C3 C2 93.1(2) . . ?
C4 C3 C13 138.3(3) . . ?
C13 C3 C2 128.5(3) . . ?
C3 C4 C1 94.6(2) . . ?
C3 C4 C5 144.5(3) . . ?
C5 C4 C1 119.4(2) . . ?
C6 C5 C4 126.9(2) . . ?
C6 C5 C10 119.1(3) . . ?
C10 C5 C4 114.0(2) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.2(3) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 120.3 . . ?
C8 C7 C6 119.4(3) . . ?
C8 C7 H7 120.3 . . ?
C7 C8 H8 119.5 . . ?
C7 C8 C9 120.9(3) . . ?
C9 C8 H8 119.5 . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.1(3) . . ?
C10 C9 H9 119.9 . . ?
C5 C10 N1 121.1(3) . . ?
C9 C10 N1 119.7(2) . . ?
C9 C10 C5 119.2(3) . . ?
O1 C11 N1 122.2(3) . . ?
O1 C11 C1 122.9(3) . . ?
N1 C11 C1 114.7(2) . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C3 120.2(3) . . ?
C14 C13 C18 117.0(2) . . ?
C18 C13 C3 122.8(3) . . ?
C13 C14 H14 118.9 . . ?
C15 C14 C13 122.2(3) . . ?
C15 C14 H14 118.9 . . ?
C14 C15 H15 120.3 . . ?
C14 C15 C16 119.3(3) . . ?
C16 C15 H15 120.3 . . ?
O2 C16 C15 125.1(3) . . ?
O2 C16 C17 115.2(3) . . ?
C15 C16 C17 119.8(2) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.6(3) . . ?
C18 C17 H17 119.7 . . ?
C13 C18 H18 119.5 . . ?
C17 C18 C13 121.0(3) . . ?
C17 C18 H18 119.5 . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
O2 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C1 C20 H20A 109.5 . . ?
C1 C20 H20B 109.5 . . ?
C1 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
