# 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. 
# 
#######################################################################

data_mx8850
_database_code_depnum_ccdc_archive 'CCDC 2068444'
loop_
_audit_author_name
_audit_author_address
Biweiyang
;Institute of Chemistry, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2021-03-06 deposited with the CCDC.	2021-03-26 downloaded from the CCDC.
;
_audit_creation_date             2020-11-02
_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         'C25 H19 N O'
_chemical_formula_sum            'C25 H19 N O'
_chemical_formula_weight         349.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNO
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'
O O 0.0106 0.0060 '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      tetragonal
_space_group_IT_number           86
_space_group_name_H-M_alt        'P 42/n'
_space_group_name_Hall           '-P 4bc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-y, x+1/2, z+1/2'
'y+1/2, -x, z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'y, -x-1/2, -z-1/2'
'-y-1/2, x, -z-1/2'

_cell_length_a                   21.9496(3)
_cell_length_b                   21.9496(3)
_cell_length_c                   7.9389(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3824.84(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    14083
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      29.8170
_cell_measurement_theta_min      2.1000
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91526
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45i (Rigaku Oxford Diffraction, 2018)
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    1.214
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_av_unetI/netI     0.0136
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.903
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            31950
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.643
_diffrn_reflns_theta_min         1.856
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.903
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -87.00 -61.00   0.50    5.00    --  -14.80  45.00  60.00   52
  2  ω    -14.00  74.00   0.50    5.00    --  -14.80  45.00  60.00  176
  3  ω   -103.00  -6.00   0.50    5.00    --  -14.80  45.00  30.00  194
  4  ω     24.00  68.00   0.50    5.00    --  -14.80  45.00  30.00   88
  5  ω     -6.00  74.00   0.50    5.00    --  -14.80  45.00 -19.01  160
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): fixed-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0047342000
_diffrn_orient_matrix_UB_12      -0.0218691000
_diffrn_orient_matrix_UB_13      0.0645108000
_diffrn_orient_matrix_UB_21      0.0319067000
_diffrn_orient_matrix_UB_22      -0.0048397000
_diffrn_orient_matrix_UB_23      0.0054788000
_diffrn_orient_matrix_UB_31      0.0020523000
_diffrn_orient_matrix_UB_32      0.0232725000
_diffrn_orient_matrix_UB_33      0.0616048000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4454
_reflns_number_total             5346
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_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         0.223
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         5346
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0438
_refine_ls_restrained_S_all      1.038
_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)+(0.0560P)²+0.7076P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1189
_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:
 C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C18(H18), C19(H19),
 C22(H22), C23(H23), C24(H24), C25(H25)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_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 0.41482(5) 0.67188(4) 0.68455(18) 0.0789(4) Uani 1 1 d . . . . .
N1 N 0.41832(4) 0.51931(4) 0.80708(11) 0.0386(2) Uani 1 1 d . . . . .
C1 C 0.29704(4) 0.47066(4) 0.42389(12) 0.03142(19) Uani 1 1 d . . . . .
C2 C 0.27147(4) 0.47861(4) 0.26761(12) 0.03123(19) Uani 1 1 d . . . . .
H2 H 0.252693 0.515397 0.241444 0.037 Uiso 1 1 calc R . . . .
C3 C 0.27329(4) 0.43165(4) 0.14598(12) 0.02928(18) Uani 1 1 d . . . . .
C4 C 0.24797(4) 0.43924(5) -0.01654(13) 0.0362(2) Uani 1 1 d . . . . .
H4 H 0.228519 0.475532 -0.044199 0.043 Uiso 1 1 calc R . . . .
C5 C 0.25189(5) 0.39373(5) -0.13292(14) 0.0431(2) Uani 1 1 d . . . . .
H5 H 0.235215 0.399132 -0.239569 0.052 Uiso 1 1 calc R . . . .
C6 C 0.28097(5) 0.33883(5) -0.09224(15) 0.0460(3) Uani 1 1 d . . . . .
H6 H 0.283756 0.308217 -0.172876 0.055 Uiso 1 1 calc R . . . .
C7 C 0.30514(5) 0.32966(5) 0.06301(15) 0.0408(2) Uani 1 1 d . . . . .
H7 H 0.323916 0.292770 0.088031 0.049 Uiso 1 1 calc R . . . .
C8 C 0.30197(4) 0.37579(4) 0.18704(12) 0.03115(19) Uani 1 1 d . . . . .
C9 C 0.32691(4) 0.36831(4) 0.35036(14) 0.0353(2) Uani 1 1 d . . . . .
H9 H 0.345268 0.331570 0.379101 0.042 Uiso 1 1 calc R . . . .
C10 C 0.32442(4) 0.41401(4) 0.46561(13) 0.0346(2) Uani 1 1 d . . . . .
H10 H 0.340745 0.408146 0.572494 0.042 Uiso 1 1 calc R . . . .
C11 C 0.30041(4) 0.52025(5) 0.54088(13) 0.0367(2) Uani 1 1 d . . . . .
C12 C 0.30928(4) 0.56055(5) 0.63826(14) 0.0390(2) Uani 1 1 d . . . . .
C13 C 0.32613(5) 0.61254(5) 0.74568(16) 0.0438(3) Uani 1 1 d . . . . .
C14 C 0.29226(7) 0.66954(6) 0.6861(2) 0.0665(4) Uani 1 1 d . . . . .
H14A H 0.301206 0.676741 0.569440 0.100 Uiso 1 1 calc GR . . . .
H14B H 0.305123 0.703974 0.751667 0.100 Uiso 1 1 calc GR . . . .
H14C H 0.249208 0.663676 0.699901 0.100 Uiso 1 1 calc GR . . . .
C15 C 0.31190(6) 0.60048(6) 0.93219(17) 0.0555(3) Uani 1 1 d . . . . .
H15A H 0.268631 0.596988 0.947039 0.083 Uiso 1 1 calc GR . . . .
H15B H 0.326967 0.633626 0.999183 0.083 Uiso 1 1 calc GR . . . .
H15C H 0.331194 0.563293 0.966890 0.083 Uiso 1 1 calc GR . . . .
C16 C 0.39544(5) 0.62216(5) 0.72121(16) 0.0472(3) Uani 1 1 d . . . . .
C17 C 0.43859(5) 0.56954(5) 0.73718(14) 0.0399(2) Uani 1 1 d . . . . .
C18 C 0.49827(6) 0.57591(6) 0.6737(2) 0.0591(3) Uani 1 1 d . . . . .
H18 H 0.511220 0.612668 0.627788 0.071 Uiso 1 1 calc R . . . .
C19 C 0.53619(6) 0.52761(7) 0.6810(2) 0.0674(4) Uani 1 1 d . . . . .
H19 H 0.575463 0.530787 0.637904 0.081 Uiso 1 1 calc R . . . .
C20 C 0.51668(5) 0.47257(6) 0.75321(15) 0.0461(3) Uani 1 1 d . . . . .
C21 C 0.45682(5) 0.47091(5) 0.81728(13) 0.0378(2) Uani 1 1 d . . . . .
C22 C 0.43562(6) 0.41700(6) 0.89294(18) 0.0543(3) Uani 1 1 d . . . . .
H22 H 0.396387 0.415413 0.936944 0.065 Uiso 1 1 calc R . . . .
C23 C 0.47236(7) 0.36713(6) 0.9020(2) 0.0624(4) Uani 1 1 d . . . . .
H23 H 0.457913 0.331784 0.952736 0.075 Uiso 1 1 calc R . . . .
C24 C 0.53132(7) 0.36816(6) 0.83642(19) 0.0609(4) Uani 1 1 d . . . . .
H24 H 0.555636 0.333530 0.842433 0.073 Uiso 1 1 calc R . . . .
C25 C 0.55312(6) 0.41956(7) 0.7640(2) 0.0617(4) Uani 1 1 d . . . . .
H25 H 0.592512 0.420028 0.720904 0.074 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 C16 1.2069(13) . ?
N1 C17 1.3120(13) . ?
N1 C21 1.3599(14) . ?
C1 C2 1.3729(13) . ?
C1 C10 1.4204(13) . ?
C1 C11 1.4327(13) . ?
C2 C3 1.4130(13) . ?
C3 C4 1.4147(13) . ?
C3 C8 1.4164(12) . ?
C4 C5 1.3634(15) . ?
C5 C6 1.4015(17) . ?
C6 C7 1.3568(17) . ?
C7 C8 1.4141(14) . ?
C8 C9 1.4169(14) . ?
C9 C10 1.3587(15) . ?
C11 C12 1.1907(14) . ?
C12 C13 1.4719(14) . ?
C13 C14 1.5303(17) . ?
C13 C15 1.5363(18) . ?
C13 C16 1.5482(16) . ?
C16 C17 1.4992(16) . ?
C17 C18 1.4104(16) . ?
C18 C19 1.349(2) . ?
C19 C20 1.4042(18) . ?
C20 C21 1.4094(15) . ?
C20 C25 1.4146(18) . ?
C21 C22 1.4062(15) . ?
C22 C23 1.3616(18) . ?
C23 C24 1.395(2) . ?
C24 C25 1.354(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
C17 N1 C21 118.08(9) . . ?
C2 C1 C10 119.67(9) . . ?
C2 C1 C11 120.69(9) . . ?
C10 C1 C11 119.48(9) . . ?
C1 C2 C3 120.89(8) . . ?
C2 C3 C4 121.75(8) . . ?
C2 C3 C8 119.13(8) . . ?
C4 C3 C8 119.11(9) . . ?
C5 C4 C3 120.46(9) . . ?
C4 C5 C6 120.18(10) . . ?
C7 C6 C5 120.99(10) . . ?
C6 C7 C8 120.47(10) . . ?
C3 C8 C9 118.85(8) . . ?
C7 C8 C3 118.78(9) . . ?
C7 C8 C9 122.36(9) . . ?
C10 C9 C8 121.01(9) . . ?
C9 C10 C1 120.41(9) . . ?
C12 C11 C1 173.51(10) . . ?
C11 C12 C13 173.30(11) . . ?
C12 C13 C14 109.44(10) . . ?
C12 C13 C15 111.95(10) . . ?
C12 C13 C16 106.27(9) . . ?
C14 C13 C15 109.87(11) . . ?
C14 C13 C16 109.09(10) . . ?
C15 C13 C16 110.14(10) . . ?
O1 C16 C13 119.99(11) . . ?
O1 C16 C17 119.64(11) . . ?
C17 C16 C13 120.33(9) . . ?
N1 C17 C16 117.96(10) . . ?
N1 C17 C18 123.33(11) . . ?
C18 C17 C16 118.69(10) . . ?
C19 C18 C17 118.68(11) . . ?
C18 C19 C20 120.36(11) . . ?
C19 C20 C21 116.99(11) . . ?
C19 C20 C25 124.06(12) . . ?
C21 C20 C25 118.94(12) . . ?
N1 C21 C20 122.53(10) . . ?
N1 C21 C22 118.50(10) . . ?
C22 C21 C20 118.97(11) . . ?
C23 C22 C21 120.20(12) . . ?
C22 C23 C24 121.12(13) . . ?
C25 C24 C23 119.99(12) . . ?
C24 C25 C20 120.76(13) . . ?

_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 1.112
_oxdiff_exptl_absorpt_empirical_full_min 0.901
