# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_xf-20200802-13-2
_database_code_depnum_ccdc_archive 'CCDC 2026038'
loop_
_audit_author_name
_audit_author_address
'Fen Xu'
;Zhengzhou University of Light Industry  Zhengzhou, Henan, China 
China
;
_audit_update_record             
;
2020-08-29 deposited with the CCDC.	2020-10-02 downloaded from the CCDC.
;
_audit_creation_date             2020-08-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '0.4(C32 H22 N O)'
_chemical_formula_sum            'C12.80 H8.80 N0.40 O0.40'
_chemical_formula_weight         174.60
_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                   9.6741(10)
_cell_length_b                   10.8198(12)
_cell_length_c                   12.5635(11)
_cell_angle_alpha                69.234(9)
_cell_angle_beta                 89.878(8)
_cell_angle_gamma                72.178(10)
_cell_volume                     1162.2(2)
_cell_formula_units_Z            5
_cell_measurement_reflns_used    2750
_cell_measurement_temperature    295.44(10)
_cell_measurement_theta_max      71.2290
_cell_measurement_theta_min      4.6450
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.580
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41701
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             458
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7737
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.873
_diffrn_reflns_theta_min         3.790
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.44(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3031
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -72.00  25.00   1.00    3.85    --  -40.80  77.00-150.00   97
  2  ω   -108.00 -18.00   1.00    3.85    --  -40.80 -57.00 -60.00   90
  3  ω   -112.00 -83.00   1.00    3.85    --  -40.80 -57.00-180.00   29
  4  ω    -67.00  31.00   1.00    3.85    --  -40.80  57.00  90.00   98
  5  ω     52.00  77.00   1.00    3.85    --   40.80 -99.00-150.00   25
  6  ω     34.00  71.00   1.00   15.41    --  105.27 -61.00 -60.00   37
  7  ω     75.00 109.00   1.00   15.41    --  105.27 -95.00  30.00   34
  8  ω     73.00 109.00   1.00   15.41    --  105.27 -95.00 -60.00   36
  9  ω     23.00  62.00   1.00   15.41    --  105.27 -95.00  30.00   39
 10  ω     64.00 110.00   1.00   15.41    --  105.27-113.00-150.00   46
 11  ω    116.00 177.00   1.00   15.41    --  105.27  61.00-120.00   61
 12  ω     48.00  75.00   1.00   15.41    --  105.27 -45.00-180.00   27
 13  ω    109.00 176.00   1.00   15.41    --  105.27 125.00  30.00   67
 14  ω     33.00 129.00   1.00   15.41    --  105.27 -45.00  90.00   96
 15  ω    126.00 177.00   1.00   15.41    --  105.27  45.00  90.00   51
 16  ω     93.00 120.00   1.00   15.41    --  105.27  45.00  90.00   27
 17  ω     82.00 133.00   1.00   15.41    --  105.27 -61.00 -60.00   51
 18  ω     40.00  87.00   1.00   15.41    --  105.27 -77.00  90.00   47
 19  ω     40.00  68.00   1.00   15.41    --  105.27 -95.00 -60.00   28
 20  ω     47.00 172.00   1.00   15.41    --  105.27   0.00  60.00  125
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1163084000
_diffrn_orient_matrix_UB_12      -0.1453532000
_diffrn_orient_matrix_UB_13      0.0315140000
_diffrn_orient_matrix_UB_21      0.0157417000
_diffrn_orient_matrix_UB_22      -0.0130582000
_diffrn_orient_matrix_UB_23      0.1258707000
_diffrn_orient_matrix_UB_31      -0.1208729000
_diffrn_orient_matrix_UB_32      -0.0682431000
_diffrn_orient_matrix_UB_33      0.0247127000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2955
_reflns_number_total             4476
_reflns_odcompleteness_completeness 99.90
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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         0.937
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.237
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4476
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1907
_refine_ls_R_factor_gt           0.1657
_refine_ls_restrained_S_all      2.237
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1000P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4066
_refine_ls_wR_factor_ref         0.4291
_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:
 C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21), C22(H22), C23(H23), C25(H25), C28(H28), C29(H29), C30(H30),
  C31(H31), C32(H32)
2.b Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C)
;
_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 0.4094(7) 0.5939(4) 0.1828(4) 0.134(2) Uani 1 1 d . . . . .
N1 N 0.1601(8) 0.7141(6) 0.3389(6) 0.1167(19) Uani 1 1 d . . . . .
C1 C 0.3931(11) 0.7592(7) 0.3071(6) 0.115(3) Uani 1 1 d . . . . .
C2 C 0.3135(12) 0.7089(6) 0.3825(6) 0.128(3) Uani 1 1 d . . . . .
C3 C 0.5180(8) 0.7506(7) 0.3462(5) 0.0951(17) Uani 1 1 d . . . . .
H3 H 0.5768 0.7815 0.2912 0.114 Uiso 1 1 calc R . . . .
C4 C 0.5782(13) 0.7029(8) 0.4568(10) 0.163(5) Uani 1 1 d . . . . .
H4 H 0.6694 0.7078 0.4740 0.196 Uiso 1 1 calc R . . . .
C5 C 0.4951(15) 0.6426(7) 0.5498(7) 0.153(5) Uani 1 1 d . . . . .
H5 H 0.5290 0.6036 0.6275 0.184 Uiso 1 1 calc R . . . .
C6 C 0.3550(10) 0.6532(5) 0.5025(5) 0.103(2) Uani 1 1 d . . . . .
C7 C 0.2551(16) 0.6101(12) 0.5679(12) 0.162(5) Uani 1 1 d . . . . .
H7 H 0.2796 0.5815 0.6464 0.195 Uiso 1 1 calc R . . . .
C8 C 0.133(2) 0.6025(11) 0.5390(12) 0.184(6) Uani 1 1 d . . . . .
H8 H 0.0787 0.5590 0.5919 0.221 Uiso 1 1 calc R . . . .
C9 C 0.0880(12) 0.6633(9) 0.4245(10) 0.156(4) Uani 1 1 d . . . . .
H9 H -0.0069 0.6701 0.4031 0.188 Uiso 1 1 calc R . . . .
C10 C 0.3340(8) 0.8149(5) 0.1857(4) 0.0934(19) Uani 1 1 d . . . . .
C11 C 0.3601(8) 0.7201(5) 0.1292(5) 0.0940(18) Uani 1 1 d . . . . .
C12 C 0.3271(5) 0.7827(4) 0.0047(4) 0.0689(11) Uani 1 1 d . . . . .
C13 C 0.2762(5) 0.9283(4) -0.0525(4) 0.0611(10) Uani 1 1 d . . . . .
C14 C 0.2458(5) 1.0176(4) 0.0141(3) 0.0603(10) Uani 1 1 d . . . . .
C15 C 0.2737(6) 0.9587(5) 0.1295(4) 0.0785(14) Uani 1 1 d . . . . .
C16 C 0.2455(7) 1.0439(5) 0.2039(4) 0.0819(15) Uani 1 1 d . . . . .
C17 C 0.1185(9) 1.0622(6) 0.2555(6) 0.103(2) Uani 1 1 d . . . . .
H17 H 0.0529 1.0183 0.2465 0.124 Uiso 1 1 calc R . . . .
C18 C 0.0880(10) 1.1445(7) 0.3201(6) 0.110(2) Uani 1 1 d . . . . .
H18 H 0.0015 1.1568 0.3536 0.132 Uiso 1 1 calc R . . . .
C19 C 0.1820(9) 1.2066(9) 0.3347(6) 0.117(3) Uani 1 1 d . . . . .
H19 H 0.1625 1.2603 0.3800 0.141 Uiso 1 1 calc R . . . .
C20 C 0.3098(10) 1.1908(12) 0.2819(9) 0.152(4) Uani 1 1 d . . . . .
H20 H 0.3750 1.2348 0.2918 0.183 Uiso 1 1 calc R . . . .
C21 C 0.3402(9) 1.1115(10) 0.2156(7) 0.123(3) Uani 1 1 d . . . . .
H21 H 0.4242 1.1033 0.1789 0.148 Uiso 1 1 calc R . . . .
C22 C 0.3549(6) 0.6971(5) -0.0582(4) 0.0765(13) Uani 1 1 d . . . . .
H22 H 0.3895 0.6005 -0.0201 0.092 Uiso 1 1 calc R . . . .
C23 C 0.3320(6) 0.7531(5) -0.1768(5) 0.0785(13) Uani 1 1 d . . . . .
H23 H 0.3504 0.6941 -0.2177 0.094 Uiso 1 1 calc R . . . .
C24 C 0.2816(6) 0.8969(5) -0.2349(4) 0.0768(13) Uani 1 1 d . . . . .
C25 C 0.2532(6) 0.9822(5) -0.1723(4) 0.0725(12) Uani 1 1 d . . . . .
H25 H 0.2176 1.0787 -0.2110 0.087 Uiso 1 1 calc R . . . .
C26 C 0.2608(10) 0.9589(7) -0.3642(5) 0.110(2) Uani 1 1 d . . . . .
H26A H 0.1868 1.0493 -0.3900 0.165 Uiso 1 1 calc GR . . . .
H26B H 0.2313 0.8988 -0.3932 0.165 Uiso 1 1 calc GR . . . .
H26C H 0.3512 0.9683 -0.3916 0.165 Uiso 1 1 calc GR . . . .
C27 C 0.1897(6) 1.1716(4) -0.0426(4) 0.0668(11) Uani 1 1 d . . . . .
C28 C 0.2830(9) 1.2461(7) -0.0727(7) 0.112(2) Uani 1 1 d . . . . .
H28 H 0.3830 1.1984 -0.0607 0.135 Uiso 1 1 calc R . . . .
C29 C 0.2358(15) 1.3882(9) -0.1200(8) 0.153(4) Uani 1 1 d . . . . .
H29 H 0.3028 1.4358 -0.1421 0.183 Uiso 1 1 calc R . . . .
C30 C 0.0938(15) 1.4592(7) -0.1345(6) 0.146(4) Uani 1 1 d . . . . .
H30 H 0.0625 1.5563 -0.1598 0.175 Uiso 1 1 calc R . . . .
C31 C -0.0100(12) 1.3880(7) -0.1117(9) 0.157(4) Uani 1 1 d . . . . .
H31 H -0.1098 1.4366 -0.1294 0.189 Uiso 1 1 calc R . . . .
C32 C 0.0413(8) 1.2450(6) -0.0626(7) 0.118(3) Uani 1 1 d . . . . .
H32 H -0.0249 1.1962 -0.0423 0.141 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 1.223(7) . ?
N1 C2 1.561(13) . ?
N1 C9 1.326(11) . ?
C1 C2 1.294(12) . ?
C1 C3 1.269(11) . ?
C1 C10 1.469(8) . ?
C2 C6 1.417(9) . ?
C3 C4 1.359(11) . ?
C4 C5 1.488(17) . ?
C5 C6 1.436(14) . ?
C6 C7 1.352(13) . ?
C7 C8 1.27(2) . ?
C8 C9 1.360(18) . ?
C10 C11 1.406(7) . ?
C10 C15 1.388(6) . ?
C11 C12 1.458(7) . ?
C12 C13 1.401(6) . ?
C12 C22 1.385(6) . ?
C13 C14 1.456(6) . ?
C13 C25 1.398(6) . ?
C14 C15 1.350(6) . ?
C14 C27 1.478(6) . ?
C15 C16 1.502(7) . ?
C16 C17 1.380(9) . ?
C16 C21 1.372(10) . ?
C17 C18 1.373(8) . ?
C18 C19 1.333(12) . ?
C19 C20 1.395(12) . ?
C20 C21 1.366(10) . ?
C22 C23 1.385(7) . ?
C23 C24 1.386(7) . ?
C24 C25 1.381(6) . ?
C24 C26 1.508(7) . ?
C27 C28 1.355(8) . ?
C27 C32 1.384(9) . ?
C28 C29 1.360(10) . ?
C29 C30 1.329(16) . ?
C30 C31 1.414(16) . ?
C31 C32 1.369(9) . ?

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
C9 N1 C2 112.2(9) . . ?
C2 C1 C10 117.6(9) . . ?
C3 C1 C2 115.9(8) . . ?
C3 C1 C10 126.4(8) . . ?
C1 C2 N1 118.1(7) . . ?
C1 C2 C6 124.1(10) . . ?
C6 C2 N1 117.8(8) . . ?
C1 C3 C4 129.5(9) . . ?
C3 C4 C5 118.5(10) . . ?
C6 C5 C4 110.4(7) . . ?
C2 C6 C5 121.4(8) . . ?
C7 C6 C2 115.6(11) . . ?
C7 C6 C5 123.0(9) . . ?
C8 C7 C6 130.2(14) . . ?
C7 C8 C9 114.4(11) . . ?
N1 C9 C8 129.2(13) . . ?
C11 C10 C1 117.4(4) . . ?
C15 C10 C1 118.6(5) . . ?
C15 C10 C11 123.4(4) . . ?
O1 C11 C10 121.0(5) . . ?
O1 C11 C12 123.4(5) . . ?
C10 C11 C12 115.6(4) . . ?
C13 C12 C11 120.9(4) . . ?
C22 C12 C11 119.4(4) . . ?
C22 C12 C13 119.6(4) . . ?
C12 C13 C14 119.3(4) . . ?
C25 C13 C12 118.3(4) . . ?
C25 C13 C14 122.4(4) . . ?
C13 C14 C27 121.2(4) . . ?
C15 C14 C13 119.3(4) . . ?
C15 C14 C27 119.5(4) . . ?
C10 C15 C16 116.3(4) . . ?
C14 C15 C10 121.3(4) . . ?
C14 C15 C16 122.4(4) . . ?
C17 C16 C15 120.0(6) . . ?
C21 C16 C15 120.7(5) . . ?
C21 C16 C17 119.2(5) . . ?
C18 C17 C16 120.8(7) . . ?
C19 C18 C17 120.1(7) . . ?
C18 C19 C20 119.8(7) . . ?
C21 C20 C19 120.7(9) . . ?
C20 C21 C16 119.3(7) . . ?
C12 C22 C23 121.0(4) . . ?
C22 C23 C24 120.2(4) . . ?
C23 C24 C26 120.6(4) . . ?
C25 C24 C23 118.8(4) . . ?
C25 C24 C26 120.6(5) . . ?
C24 C25 C13 122.1(4) . . ?
C28 C27 C14 120.7(5) . . ?
C28 C27 C32 117.7(5) . . ?
C32 C27 C14 121.6(5) . . ?
C27 C28 C29 122.4(8) . . ?
C30 C29 C28 120.0(9) . . ?
C29 C30 C31 120.4(6) . . ?
C32 C31 C30 117.8(9) . . ?
C31 C32 C27 121.4(8) . . ?

_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 2.619
_oxdiff_exptl_absorpt_empirical_full_min 0.532
