# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_exp_15203
_database_code_depnum_ccdc_archive 'CCDC 1959346'
loop_
_audit_author_name
_audit_author_address
'Li Nan'
;Shaanxi Normal University
China
;
_audit_update_record             
;
2019-10-15 deposited with the CCDC.	2020-01-28 downloaded from the CCDC.
;
_audit_creation_date             2019-07-04
_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         'C21 H22 N3 O2'
_chemical_formula_sum            'C21 H22 N3 O2'
_chemical_formula_weight         348.41
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.5347(3)
_cell_length_b                   11.4519(5)
_cell_length_c                   14.2937(6)
_cell_angle_alpha                112.503(4)
_cell_angle_beta                 95.468(4)
_cell_angle_gamma                100.753(3)
_cell_volume                     954.35(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6391
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.3480
_cell_measurement_theta_min      4.2230
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.635
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61624
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             370
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17579
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.910
_diffrn_reflns_theta_min         4.259
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0356
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     11.00 105.00   1.00    3.48    --   37.78  77.00  60.00   94
  2  ω    -30.00  65.00   1.00    3.48    --   37.78 -77.00 -60.00   95
  3  ω     -4.00  77.00   1.00    3.48    --   37.78 -99.00-120.00   81
  4  ω     -4.00  77.00   1.00    3.48    --   37.78 -99.00-180.00   81
  5  ω    -31.00  57.00   1.00    3.48    --   37.78 -37.00-180.00   88
  6  ω     19.00 107.00   1.00    3.48    --   37.78  37.00   0.00   88
  7  ω     21.00 105.00   1.00    3.48    --   37.78  57.00 120.00   84
  8  ω     39.00 123.00   1.00   13.90    --  108.00-127.00 -64.00   84
  9  ω     87.00 178.00   1.00   13.90    --  108.00  30.00 -60.00   91
 10  ω    100.00 178.00   1.00   13.90    --  108.00 111.00  90.00   78
 11  ω     40.00 135.00   1.00   13.90    --  108.00 -77.00 120.00   95
 12  ω     38.00 116.00   1.00   13.90    --  108.00-111.00  90.00   78
 13  ω    100.00 178.00   1.00   13.90    --  108.00 111.00  60.00   78
 14  ω     38.00 129.00   1.00   13.90    --  108.00 -30.00  30.00   91
 15  ω     40.00 125.00   1.00   13.90    --  108.00 -45.00 120.00   85
 16  ω     40.00 125.00   1.00   13.90    --  108.00 -45.00 -90.00   85
 17  ω     41.00 126.00   1.00   13.90    --  108.00 -61.00   0.00   85
 18  ω     39.00 109.00   1.00   13.90    --  108.00 -94.00 -30.00   70
 19  ω     39.00 177.00   1.00   13.90    --  108.00   0.00  60.00  138
 20  ω     21.00 105.00   1.00    3.48    --   37.78  57.00-180.00   84
 21  ω     21.00 105.00   1.00    3.48    --   37.78  57.00-120.00   84
 22  ω     11.00 105.00   1.00    3.48    --   37.78  77.00 -90.00   94
 23  ω    -31.00  57.00   1.00    3.48    --   37.78 -37.00 -60.00   88
 24  ω     11.00 105.00   1.00    3.48    --   37.78  77.00 -30.00   94
 25  ω    -29.00  55.00   1.00    3.48    --   37.78 -57.00  30.00   84
 26  ω     70.00 178.00   1.00   13.90    --  108.00  15.00-150.00  108
 27  ω     87.00 178.00   1.00   13.90    --  108.00  30.00 150.00   91
 28  ω     91.00 176.00   1.00   13.90    --  108.00  45.00-150.00   85
 29  ω     81.00 176.00   1.00   13.90    --  108.00  77.00  30.00   95
 30  ω     87.00 178.00   1.00   13.90    --  108.00  30.00   0.00   91
 31  ω     91.00 176.00   1.00   13.90    --  108.00  45.00-120.00   85
 32  ω     87.00 178.00   1.00   13.90    --  108.00  30.00 -30.00   91
 33  ω     87.00 178.00   1.00   13.90    --  108.00  30.00  30.00   91
 34  ω     81.00 176.00   1.00   13.90    --  108.00  77.00  60.00   95
 35  ω     81.00 176.00   1.00   13.90    --  108.00  77.00-120.00   95
 36  ω     81.00 176.00   1.00   13.90    --  108.00  77.00 150.00   95
 37  ω     87.00 178.00   1.00   13.90    --  108.00  30.00 120.00   91
 38  ω     11.00 105.00   1.00    3.48    --   37.78  77.00-180.00   94
 39  ω     11.00 105.00   1.00    3.48    --   37.78  77.00 120.00   94
 40  ω     11.00 105.00   1.00    3.48    --   37.78  77.00-120.00   94
 41  ω     21.00 105.00   1.00    3.48    --   37.78  57.00 -30.00   84
 42  ω     11.00 105.00   1.00    3.48    --   37.78  77.00   0.00   94
 43  ω    -29.00  55.00   1.00    3.48    --   37.78 -57.00  90.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0151416000
_diffrn_orient_matrix_UB_12      0.1092043000
_diffrn_orient_matrix_UB_13      0.1069849000
_diffrn_orient_matrix_UB_21      -0.0356726000
_diffrn_orient_matrix_UB_22      0.0931872000
_diffrn_orient_matrix_UB_23      -0.0507735000
_diffrn_orient_matrix_UB_31      -0.2410212000
_diffrn_orient_matrix_UB_32      -0.0438034000
_diffrn_orient_matrix_UB_33      -0.0078424000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3116
_reflns_number_total             3689
_reflns_odcompleteness_completeness 99.91
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3689
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0469
_refine_ls_restrained_S_all      1.047
_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)+(0.0791P)²+0.1681P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1338
_refine_ls_wR_factor_ref         0.1434
_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:
 C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,
 H22B), C23(H23A,H23B), C24(H24A,H24B), C26(H26A,H26B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C14(H14)
;
_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
O1 O 0.3730(2) 0.37556(12) 0.80298(11) 0.0697(4) Uani 1 1 d . . . . .
C2 C 0.8744(2) 0.07995(12) 0.55750(10) 0.0376(3) Uani 1 1 d . . . . .
C3 C 0.8998(2) -0.03109(13) 0.57073(10) 0.0391(3) Uani 1 1 d . . . . .
H3 H 0.832280 -0.052986 0.618231 0.047 Uiso 1 1 calc R . . . .
C4 C 0.7453(2) 0.16131(13) 0.62068(10) 0.0391(3) Uani 1 1 d . . . . .
C5 C 0.8101(2) 0.29653(14) 0.66507(11) 0.0462(3) Uani 1 1 d . . . . .
H5 H 0.937433 0.337165 0.654489 0.055 Uiso 1 1 calc R . . . .
C6 C 0.9356(2) 0.21588(13) 0.45680(10) 0.0411(3) Uani 1 1 d . . . . .
H6 H 0.801017 0.231143 0.459790 0.049 Uiso 1 1 calc R . . . .
N7 N 0.1083(2) 0.87252(13) 1.06145(10) 0.0554(4) Uani 1 1 d . . . . .
C8 C 0.9770(2) 0.11086(12) 0.48460(10) 0.0381(3) Uani 1 1 d . . . . .
C9 C 0.4344(2) 0.17806(15) 0.69858(12) 0.0504(4) Uani 1 1 d . . . . .
H9 H 0.307050 0.137598 0.709257 0.060 Uiso 1 1 calc R . . . .
C10 C 0.5553(2) 0.10377(13) 0.63896(11) 0.0443(3) Uani 1 1 d . . . . .
H10 H 0.508896 0.013430 0.610410 0.053 Uiso 1 1 calc R . . . .
C11 C 0.5016(3) 0.31267(15) 0.74268(12) 0.0493(4) Uani 1 1 d . . . . .
O12 O 0.1198(3) 1.12093(13) 1.21756(10) 0.0775(4) Uani 1 1 d . . . . .
C13 C 0.9975(3) 0.37589(15) 0.38560(13) 0.0528(4) Uani 1 1 d . . . . .
C14 C 0.6890(3) 0.37221(14) 0.72484(12) 0.0517(4) Uani 1 1 d . . . . .
H14 H 0.733697 0.462609 0.752773 0.062 Uiso 1 1 calc R . . . .
C15 C 1.0720(2) 0.29214(13) 0.42752(11) 0.0446(3) Uani 1 1 d . . . . .
N16 N 0.9329(3) 0.43774(16) 0.35033(15) 0.0785(5) Uani 1 1 d . . . . .
C17 C 1.2942(3) 0.29715(16) 0.43435(14) 0.0574(4) Uani 1 1 d . . . . .
C18 C 0.1293(3) 0.73878(18) 1.02942(14) 0.0630(5) Uani 1 1 d . . . . .
H18A H -0.010293 0.680245 0.999973 0.076 Uiso 1 1 calc R . . . .
H18B H 0.183273 0.726884 1.089924 0.076 Uiso 1 1 calc R . . . .
C19 C 0.2597(3) 0.55558(18) 0.91092(15) 0.0679(5) Uani 1 1 d . . . . .
H19A H 0.284172 0.532108 0.968711 0.081 Uiso 1 1 calc R . . . .
H19B H 0.117664 0.508463 0.872855 0.081 Uiso 1 1 calc R . . . .
C20 C 0.4171(3) 0.51411(17) 0.84177(14) 0.0626(5) Uani 1 1 d . . . . .
H20A H 0.401182 0.541353 0.785586 0.075 Uiso 1 1 calc R . . . .
H20B H 0.560749 0.552737 0.880325 0.075 Uiso 1 1 calc R . . . .
C21 C 0.2738(3) 0.70063(18) 0.95154(15) 0.0667(5) Uani 1 1 d . . . . .
H21A H 0.233246 0.723212 0.894761 0.080 Uiso 1 1 calc R . . . .
H21B H 0.418824 0.748565 0.983798 0.080 Uiso 1 1 calc R . . . .
C22 C -0.0502(3) 0.89354(19) 1.12780(14) 0.0648(5) Uani 1 1 d . . . . .
H22A H -0.007486 0.876757 1.187411 0.078 Uiso 1 1 calc R . . . .
H22B H -0.185114 0.833189 1.090427 0.078 Uiso 1 1 calc R . . . .
C23 C -0.0747(3) 1.0309(2) 1.16264(15) 0.0726(5) Uani 1 1 d . . . . .
H23A H -0.123054 1.046493 1.103172 0.087 Uiso 1 1 calc R . . . .
H23B H -0.180537 1.042938 1.206397 0.087 Uiso 1 1 calc R . . . .
C24 C 0.3063(3) 0.96746(18) 1.11733(14) 0.0647(5) Uani 1 1 d . . . . .
H24A H 0.410895 0.957898 1.072863 0.078 Uiso 1 1 calc R . . . .
H24B H 0.358902 0.951731 1.176123 0.078 Uiso 1 1 calc R . . . .
N25 N 1.4697(3) 0.3029(2) 0.44062(19) 0.0907(6) Uani 1 1 d . . . . .
C26 C 0.2755(4) 1.1042(2) 1.15386(16) 0.0788(6) Uani 1 1 d . . . . .
H26A H 0.408778 1.165862 1.192151 0.095 Uiso 1 1 calc R . . . .
H26B H 0.232023 1.121822 1.094787 0.095 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 C11 1.3627(17) . ?
O1 C20 1.426(2) . ?
C2 C3 1.3919(17) . ?
C2 C4 1.4796(17) . ?
C2 C8 1.4099(18) . ?
C3 C8 1.3966(17) 2_756 ?
C4 C5 1.3898(19) . ?
C4 C10 1.390(2) . ?
C5 C14 1.3878(19) . ?
C6 C8 1.4643(17) . ?
C6 C15 1.339(2) . ?
N7 C18 1.459(2) . ?
N7 C22 1.461(2) . ?
N7 C24 1.451(2) . ?
C9 C10 1.3777(19) . ?
C9 C11 1.385(2) . ?
C11 C14 1.382(2) . ?
O12 C23 1.413(3) . ?
O12 C26 1.420(2) . ?
C13 C15 1.4400(19) . ?
C13 N16 1.131(2) . ?
C15 C17 1.435(2) . ?
C17 N25 1.129(2) . ?
C18 C21 1.518(2) . ?
C19 C20 1.509(2) . ?
C19 C21 1.516(2) . ?
C22 C23 1.502(3) . ?
C24 C26 1.509(3) . ?

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 O1 C20 118.69(13) . . ?
C3 C2 C4 119.39(11) . . ?
C3 C2 C8 117.82(11) . . ?
C8 C2 C4 122.79(11) . . ?
C2 C3 C8 122.50(12) . 2_756 ?
C5 C4 C2 121.74(13) . . ?
C5 C4 C10 117.76(12) . . ?
C10 C4 C2 120.49(12) . . ?
C14 C5 C4 121.43(14) . . ?
C15 C6 C8 126.58(13) . . ?
C18 N7 C22 109.34(14) . . ?
C24 N7 C18 112.42(14) . . ?
C24 N7 C22 108.55(13) . . ?
C2 C8 C6 120.82(11) . . ?
C3 C8 C2 119.68(11) 2_756 . ?
C3 C8 C6 119.07(11) 2_756 . ?
C10 C9 C11 120.32(14) . . ?
C9 C10 C4 121.24(13) . . ?
O1 C11 C9 115.06(14) . . ?
O1 C11 C14 125.41(14) . . ?
C14 C11 C9 119.52(13) . . ?
C23 O12 C26 109.85(15) . . ?
N16 C13 C15 177.4(2) . . ?
C11 C14 C5 119.72(14) . . ?
C6 C15 C13 119.88(13) . . ?
C6 C15 C17 124.32(12) . . ?
C17 C15 C13 115.80(13) . . ?
N25 C17 C15 179.0(2) . . ?
N7 C18 C21 114.42(15) . . ?
C20 C19 C21 112.97(17) . . ?
O1 C20 C19 106.47(15) . . ?
C19 C21 C18 110.54(16) . . ?
N7 C22 C23 110.67(16) . . ?
O12 C23 C22 110.69(16) . . ?
N7 C24 C26 110.79(16) . . ?
O12 C26 C24 111.04(17) . . ?

_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 1.387
_oxdiff_exptl_absorpt_empirical_full_min 0.669
