# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_191118_zj_22b_0ma
_database_code_depnum_ccdc_archive 'CCDC 1968676'
loop_
_audit_author_name
_audit_author_address
'Jing Zhou'
;Zhejiang University of Technology
China
;
_audit_update_record             
;
2019-11-28 deposited with the CCDC.	2019-12-02 downloaded from the CCDC.
;
_audit_creation_date             2019-11-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H23 N3'
_chemical_formula_sum            'C23 H23 N3'
_chemical_formula_weight         341.44
_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 0.0033 0.0016 '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 0.0061 0.0033 '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                   16.0465(3)
_cell_length_b                   9.2007(2)
_cell_length_c                   12.4727(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.1700(10)
_cell_angle_gamma                90
_cell_volume                     1840.14(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9918
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      33.38
_cell_measurement_theta_min      2.54
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.966
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_correction_T_min  0.6984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0702 before and 0.0387 after correction.
The Ratio of minimum to maximum transmission is 0.9354.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.806
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20316
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.806
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.694
_diffrn_reflns_theta_min         2.540
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.806
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5001
_reflns_number_total             5919
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.437
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         5919
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0454
_refine_ls_restrained_S_all      1.051
_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)+(0.0615P)²+0.4980P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1278
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14),
 C15(H15), C17(H17), C18(H18)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C)
;
_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
N1 N 0.44061(5) 0.68412(9) 0.45946(7) 0.02721(18) Uani 1 1 d . . . . .
N2 N 0.41714(6) 0.63310(10) 0.27193(7) 0.02870(19) Uani 1 1 d . . . . .
N3 N 0.34524(6) 0.40705(10) 0.23644(7) 0.02763(18) Uani 1 1 d . . . . .
C1 C 0.41983(7) 0.61631(12) 0.55375(8) 0.0290(2) Uani 1 1 d . . . . .
H1 H 0.433884 0.651570 0.623706 0.035 Uiso 1 1 calc R . . . .
C2 C 0.37631(6) 0.49163(11) 0.53214(8) 0.0265(2) Uani 1 1 d . . . . .
H2 H 0.354673 0.426127 0.582976 0.032 Uiso 1 1 calc R . . . .
C3 C 0.36969(6) 0.47907(10) 0.41797(7) 0.02182(17) Uani 1 1 d . . . . .
C4 C 0.41007(6) 0.60244(10) 0.37596(8) 0.02335(18) Uani 1 1 d . . . . .
C5 C 0.38183(7) 0.53207(12) 0.20832(8) 0.0303(2) Uani 1 1 d . . . . .
H5 H 0.382671 0.550937 0.133481 0.036 Uiso 1 1 calc R . . . .
C6 C 0.33902(6) 0.37883(10) 0.34175(7) 0.02163(17) Uani 1 1 d . . . . .
C7 C 0.30522(6) 0.23365(10) 0.36962(7) 0.02170(17) Uani 1 1 d . . . . .
C8 C 0.34031(6) 0.11340(11) 0.31946(8) 0.02655(19) Uani 1 1 d . . . . .
H8 H 0.381474 0.128287 0.267806 0.032 Uiso 1 1 calc R . . . .
C9 C 0.31605(7) -0.02709(11) 0.34383(9) 0.0308(2) Uani 1 1 d . . . . .
H9 H 0.339790 -0.107540 0.308265 0.037 Uiso 1 1 calc R . . . .
C10 C 0.25696(8) -0.04941(11) 0.42039(9) 0.0327(2) Uani 1 1 d . . . . .
H10 H 0.241270 -0.145442 0.439031 0.039 Uiso 1 1 calc R . . . .
C11 C 0.22076(7) 0.06884(11) 0.46979(9) 0.0293(2) Uani 1 1 d . . . . .
H11 H 0.179915 0.052533 0.521648 0.035 Uiso 1 1 calc R . . . .
C12 C 0.24319(6) 0.21169(10) 0.44479(7) 0.02243(18) Uani 1 1 d . . . . .
C13 C 0.19885(6) 0.33405(10) 0.49518(7) 0.02154(17) Uani 1 1 d . . . . .
C14 C 0.16900(6) 0.45112(11) 0.43397(8) 0.02412(18) Uani 1 1 d . . . . .
H14 H 0.176596 0.452026 0.358802 0.029 Uiso 1 1 calc R . . . .
C15 C 0.12831(6) 0.56647(11) 0.48135(8) 0.02481(19) Uani 1 1 d . . . . .
H15 H 0.108183 0.644530 0.437756 0.030 Uiso 1 1 calc R . . . .
C16 C 0.11634(6) 0.57017(10) 0.59176(8) 0.02243(18) Uani 1 1 d . . . . .
C17 C 0.14537(6) 0.45113(11) 0.65213(8) 0.02525(19) Uani 1 1 d . . . . .
H17 H 0.137527 0.449820 0.727240 0.030 Uiso 1 1 calc R . . . .
C18 C 0.18536(6) 0.33479(11) 0.60512(8) 0.02459(19) Uani 1 1 d . . . . .
H18 H 0.203709 0.254967 0.648188 0.030 Uiso 1 1 calc R . . . .
C19 C 0.07870(6) 0.70328(11) 0.64542(8) 0.02614(19) Uani 1 1 d . . . . .
C20 C 0.15104(8) 0.79781(12) 0.68987(10) 0.0349(2) Uani 1 1 d . . . . .
H20A H 0.183191 0.743337 0.744830 0.052 Uiso 1 1 calc GR . . . .
H20B H 0.128691 0.886367 0.721645 0.052 Uiso 1 1 calc GR . . . .
H20C H 0.187369 0.823979 0.631477 0.052 Uiso 1 1 calc GR . . . .
C21 C 0.02528(8) 0.79400(13) 0.56590(10) 0.0363(2) Uani 1 1 d . . . . .
H21A H 0.060962 0.836451 0.512064 0.054 Uiso 1 1 calc GR . . . .
H21B H -0.002462 0.871908 0.604526 0.054 Uiso 1 1 calc GR . . . .
H21C H -0.016813 0.731607 0.530268 0.054 Uiso 1 1 calc GR . . . .
C22 C 0.02424(8) 0.65847(14) 0.73865(10) 0.0394(3) Uani 1 1 d . . . . .
H22A H -0.019825 0.592536 0.712033 0.059 Uiso 1 1 calc GR . . . .
H22B H -0.001002 0.745217 0.769450 0.059 Uiso 1 1 calc GR . . . .
H22C H 0.058822 0.609091 0.793906 0.059 Uiso 1 1 calc GR . . . .
C23 C 0.49444(7) 0.81049(12) 0.45080(11) 0.0358(2) Uani 1 1 d . . . . .
H23A H 0.531834 0.796474 0.391334 0.054 Uiso 1 1 calc GR . . . .
H23B H 0.527539 0.822829 0.517830 0.054 Uiso 1 1 calc GR . . . .
H23C H 0.460210 0.897278 0.437387 0.054 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
N1 C1 1.3832(14) . ?
N1 C4 1.3605(13) . ?
N1 C23 1.4548(13) . ?
N2 C4 1.3369(13) . ?
N2 C5 1.3344(14) . ?
N3 C5 1.3440(13) . ?
N3 C6 1.3463(12) . ?
C1 H1 0.9500 . ?
C1 C2 1.3646(14) . ?
C2 H2 0.9500 . ?
C2 C3 1.4286(13) . ?
C3 C4 1.4172(13) . ?
C3 C6 1.4004(13) . ?
C5 H5 0.9500 . ?
C6 C7 1.4878(13) . ?
C7 C8 1.3996(13) . ?
C7 C12 1.4075(13) . ?
C8 H8 0.9500 . ?
C8 C9 1.3870(15) . ?
C9 H9 0.9500 . ?
C9 C10 1.3863(17) . ?
C10 H10 0.9500 . ?
C10 C11 1.3885(15) . ?
C11 H11 0.9500 . ?
C11 C12 1.4010(13) . ?
C12 C13 1.4842(13) . ?
C13 C14 1.3946(13) . ?
C13 C18 1.3963(13) . ?
C14 H14 0.9500 . ?
C14 C15 1.3897(13) . ?
C15 H15 0.9500 . ?
C15 C16 1.3981(13) . ?
C16 C17 1.3989(13) . ?
C16 C19 1.5308(13) . ?
C17 H17 0.9500 . ?
C17 C18 1.3893(14) . ?
C18 H18 0.9500 . ?
C19 C20 1.5371(15) . ?
C19 C21 1.5333(15) . ?
C19 C22 1.5371(15) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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
C1 N1 C23 125.91(9) . . ?
C4 N1 C1 108.07(8) . . ?
C4 N1 C23 125.61(9) . . ?
C5 N2 C4 112.36(9) . . ?
C5 N3 C6 117.97(9) . . ?
N1 C1 H1 124.8 . . ?
C2 C1 N1 110.44(9) . . ?
C2 C1 H1 124.8 . . ?
C1 C2 H2 126.8 . . ?
C1 C2 C3 106.44(9) . . ?
C3 C2 H2 126.8 . . ?
C4 C3 C2 106.61(8) . . ?
C6 C3 C2 137.81(9) . . ?
C6 C3 C4 115.49(8) . . ?
N1 C4 C3 108.42(8) . . ?
N2 C4 N1 125.81(9) . . ?
N2 C4 C3 125.78(9) . . ?
N2 C5 N3 128.37(9) . . ?
N2 C5 H5 115.8 . . ?
N3 C5 H5 115.8 . . ?
N3 C6 C3 119.88(8) . . ?
N3 C6 C7 116.25(8) . . ?
C3 C6 C7 123.68(8) . . ?
C8 C7 C6 116.67(8) . . ?
C8 C7 C12 119.40(9) . . ?
C12 C7 C6 123.90(8) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 C7 121.18(9) . . ?
C9 C8 H8 119.4 . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.60(9) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.88(10) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 119.3 . . ?
C10 C11 C12 121.40(10) . . ?
C12 C11 H11 119.3 . . ?
C7 C12 C13 122.39(8) . . ?
C11 C12 C7 118.50(9) . . ?
C11 C12 C13 119.08(9) . . ?
C14 C13 C12 120.95(8) . . ?
C14 C13 C18 118.11(8) . . ?
C18 C13 C12 120.95(8) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 120.94(9) . . ?
C15 C14 H14 119.5 . . ?
C14 C15 H15 119.3 . . ?
C14 C15 C16 121.45(9) . . ?
C16 C15 H15 119.3 . . ?
C15 C16 C17 117.11(9) . . ?
C15 C16 C19 121.42(8) . . ?
C17 C16 C19 121.33(8) . . ?
C16 C17 H17 119.1 . . ?
C18 C17 C16 121.72(9) . . ?
C18 C17 H17 119.1 . . ?
C13 C18 H18 119.7 . . ?
C17 C18 C13 120.63(9) . . ?
C17 C18 H18 119.7 . . ?
C16 C19 C20 107.77(8) . . ?
C16 C19 C21 111.89(8) . . ?
C16 C19 C22 111.17(9) . . ?
C20 C19 C22 108.79(9) . . ?
C21 C19 C20 108.75(9) . . ?
C21 C19 C22 108.39(9) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N1 C23 H23A 109.5 . . ?
N1 C23 H23B 109.5 . . ?
N1 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
