# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_mo_20220716c_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2210934'
loop_
_audit_author_name
_audit_author_address
ni
;Anhui Normal University
China
;
_audit_update_record             
;
2022-10-03 deposited with the CCDC.	2023-04-13 downloaded from the CCDC.
;
_audit_creation_date             2022-07-16
_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         'C28 H22 N2 O'
_chemical_formula_sum            'C28 H21 N2 O'
_chemical_formula_weight         401.47
_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'
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      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                   9.820(4)
_cell_length_b                   10.002(5)
_cell_length_c                   11.566(5)
_cell_angle_alpha                74.516(14)
_cell_angle_beta                 81.314(13)
_cell_angle_gamma                76.320(13)
_cell_volume                     1059.1(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6590
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.080
_cell_measurement_theta_min      2.842
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6911
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0764 before and 0.0632 after correction. The Ratio of minimum to maximum transmission is 0.9269. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             422
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0852
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            36498
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.562
_diffrn_reflns_theta_min         2.712
_diffrn_ambient_temperature      273.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2928
_reflns_number_total             4849
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.614
_refine_diff_density_min         -0.635
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4849
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1146
_refine_ls_R_factor_gt           0.0638
_refine_ls_restrained_S_all      1.041
_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)+(0.0852P)²+0.4426P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1571
_refine_ls_wR_factor_ref         0.1888
_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. Restrained distances
 H5-H15
 1.95 with sigma of 0.001
3.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
3.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C28(H28), C25(H25), C3(H3), C5(H5), C15(H15), C26(H26), C27(H27),
 C4(H4), C22(H22), C18(H18), C20(H20), C21(H21), C19(H19)
3.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.54484(19) 0.69606(19) 0.46581(15) 0.0377(4) Uani 1 1 d . . . . .
O1 O 1.06324(19) 0.5589(2) 0.63716(18) 0.0692(6) Uani 1 1 d . . . . .
N2 N 0.6564(2) 0.8636(2) 0.76116(17) 0.0436(5) Uani 1 1 d . . . . .
C9 C 0.5740(2) 0.7530(2) 0.55613(18) 0.0351(5) Uani 1 1 d . . . . .
C8 C 0.4468(2) 0.8432(2) 0.58808(18) 0.0358(5) Uani 1 1 d . . . . .
C24 C 0.4192(2) 0.9317(2) 0.67589(19) 0.0379(5) Uani 1 1 d . . . . .
C10 C 0.7077(2) 0.7196(2) 0.60218(18) 0.0367(5) Uani 1 1 d . . . . .
C11 C 0.7327(2) 0.7787(2) 0.70035(19) 0.0375(5) Uani 1 1 d . . . . .
C6 C 0.4041(2) 0.7470(2) 0.44447(19) 0.0393(5) Uani 1 1 d . . . . .
C7 C 0.3450(2) 0.8375(2) 0.5190(2) 0.0419(5) Uani 1 1 d . . . . .
H7 H 0.252002 0.886773 0.522264 0.050 Uiso 1 1 calc R . . . .
C23 C 0.5157(2) 0.9360(2) 0.75269(19) 0.0396(5) Uani 1 1 d . . . . .
C12 C 0.8853(2) 0.7246(3) 0.7270(2) 0.0441(5) Uani 1 1 d . . . . .
C28 C 0.4731(3) 1.0246(3) 0.8332(2) 0.0508(6) Uani 1 1 d . . . . .
H28 H 0.537097 1.026643 0.884014 0.061 Uiso 1 1 calc R . . . .
C25 C 0.2850(3) 1.0197(3) 0.6845(2) 0.0484(6) Uani 1 1 d . . . . .
H25 H 0.219752 1.019771 0.634008 0.058 Uiso 1 1 calc R . . . .
C3 C 0.4320(3) 0.6098(3) 0.2990(2) 0.0524(6) Uani 1 1 d . . . . .
H3 H 0.396567 0.579322 0.242559 0.063 Uiso 1 1 calc R . . . .
C5 C 0.6246(2) 0.6019(2) 0.4002(2) 0.0468(6) Uani 1 1 d . . . . .
H5 H 0.718874 0.566654 0.413529 0.056 Uiso 1 1 calc DR . . . .
C16 C 0.9060(3) 0.6489(3) 0.8592(2) 0.0524(6) Uani 1 1 d . . . . .
H16A H 1.006186 0.624179 0.867762 0.063 Uiso 1 1 calc R . . . .
H16B H 0.863778 0.715923 0.908047 0.063 Uiso 1 1 calc R . . . .
C14 C 0.9419(2) 0.6277(3) 0.6432(2) 0.0473(6) Uani 1 1 d . . . . .
C2 C 0.3460(3) 0.7021(3) 0.3599(2) 0.0478(6) Uani 1 1 d . . . . .
C15 C 0.8366(2) 0.6352(3) 0.5746(2) 0.0534(7) Uani 1 1 d . . . . .
H15 H 0.850567 0.587106 0.513804 0.064 Uiso 1 1 calc DR . . . .
C17 C 0.8474(3) 0.5173(3) 0.9106(2) 0.0525(6) Uani 1 1 d . . . . .
C26 C 0.2457(3) 1.1054(3) 0.7640(2) 0.0560(7) Uani 1 1 d . . . . .
H26 H 0.155610 1.161375 0.766925 0.067 Uiso 1 1 calc R . . . .
C27 C 0.3411(3) 1.1079(3) 0.8397(2) 0.0582(7) Uani 1 1 d . . . . .
H27 H 0.315930 1.165354 0.894034 0.070 Uiso 1 1 calc R . . . .
C4 C 0.5743(3) 0.5607(3) 0.3214(2) 0.0518(6) Uani 1 1 d . . . . .
H4 H 0.632652 0.498155 0.279321 0.062 Uiso 1 1 calc R . . . .
C13 C 0.9655(3) 0.8470(3) 0.6913(3) 0.0709(8) Uani 1 1 d . . . . .
H13A H 0.949168 0.899809 0.610402 0.106 Uiso 1 1 calc GR . . . .
H13B H 1.064399 0.809003 0.695997 0.106 Uiso 1 1 calc GR . . . .
H13C H 0.932731 0.908388 0.745328 0.106 Uiso 1 1 calc GR . . . .
C22 C 0.9243(3) 0.3857(3) 0.8958(3) 0.0651(8) Uani 1 1 d . . . . .
H22 H 1.009969 0.380402 0.848488 0.078 Uiso 1 1 calc R . . . .
C1 C 0.1923(3) 0.7561(3) 0.3427(3) 0.0712(9) Uani 1 1 d . . . . .
H1A H 0.139002 0.751010 0.419976 0.107 Uiso 1 1 calc GR . . . .
H1B H 0.162129 0.699113 0.300658 0.107 Uiso 1 1 calc GR . . . .
H1C H 0.177574 0.852772 0.296668 0.107 Uiso 1 1 calc GR . . . .
C18 C 0.7196(3) 0.5207(4) 0.9811(3) 0.0722(8) Uani 1 1 d . . . . .
H18 H 0.665605 0.607156 0.991906 0.087 Uiso 1 1 calc R . . . .
C20 C 0.7491(5) 0.2673(4) 1.0198(3) 0.0900(11) Uani 1 1 d . . . . .
H20 H 0.716270 0.184519 1.055623 0.108 Uiso 1 1 calc R . . . .
C21 C 0.8751(4) 0.2627(4) 0.9505(3) 0.0817(10) Uani 1 1 d . . . . .
H21 H 0.928466 0.175890 0.939953 0.098 Uiso 1 1 calc R . . . .
C19 C 0.6712(4) 0.3964(5) 1.0358(3) 0.0924(11) Uani 1 1 d . . . . .
H19 H 0.585783 0.400459 1.083518 0.111 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
N1 C9 1.408(3) . ?
N1 C6 1.391(3) . ?
N1 C5 1.389(3) . ?
O1 C14 1.230(3) . ?
N2 C11 1.279(3) . ?
N2 C23 1.405(3) . ?
C9 C8 1.421(3) . ?
C9 C10 1.424(3) . ?
C8 C24 1.473(3) . ?
C8 C7 1.390(3) . ?
C24 C23 1.409(3) . ?
C24 C25 1.407(3) . ?
C10 C11 1.487(3) . ?
C10 C15 1.390(3) . ?
C11 C12 1.517(3) . ?
C6 C7 1.385(3) . ?
C6 C2 1.417(3) . ?
C23 C28 1.405(3) . ?
C12 C16 1.535(3) . ?
C12 C14 1.507(3) . ?
C12 C13 1.542(4) . ?
C28 C27 1.369(4) . ?
C25 C26 1.373(3) . ?
C3 C2 1.364(4) . ?
C3 C4 1.406(4) . ?
C5 C4 1.296(3) . ?
C16 C17 1.501(4) . ?
C14 C15 1.372(3) . ?
C2 C1 1.502(4) . ?
C17 C22 1.394(4) . ?
C17 C18 1.388(4) . ?
C26 C27 1.384(4) . ?
C22 C21 1.386(4) . ?
C18 C19 1.394(5) . ?
C20 C21 1.367(5) . ?
C20 C19 1.380(5) . ?

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
C6 N1 C9 109.08(18) . . ?
C5 N1 C9 133.66(19) . . ?
C5 N1 C6 117.25(18) . . ?
C11 N2 C23 129.9(2) . . ?
N1 C9 C8 106.30(18) . . ?
N1 C9 C10 123.76(19) . . ?
C8 C9 C10 129.94(19) . . ?
C9 C8 C24 129.0(2) . . ?
C7 C8 C9 107.76(19) . . ?
C7 C8 C24 123.2(2) . . ?
C23 C24 C8 125.7(2) . . ?
C25 C24 C8 117.6(2) . . ?
C25 C24 C23 116.7(2) . . ?
C9 C10 C11 121.95(19) . . ?
C15 C10 C9 133.37(19) . . ?
C15 C10 C11 104.68(18) . . ?
N2 C11 C10 134.3(2) . . ?
N2 C11 C12 116.8(2) . . ?
C10 C11 C12 108.82(18) . . ?
N1 C6 C2 120.5(2) . . ?
C7 C6 N1 107.63(19) . . ?
C7 C6 C2 131.8(2) . . ?
C6 C7 C8 109.2(2) . . ?
N2 C23 C24 129.03(19) . . ?
N2 C23 C28 111.9(2) . . ?
C28 C23 C24 119.1(2) . . ?
C11 C12 C16 114.4(2) . . ?
C11 C12 C13 110.7(2) . . ?
C16 C12 C13 107.9(2) . . ?
C14 C12 C11 102.93(19) . . ?
C14 C12 C16 112.4(2) . . ?
C14 C12 C13 108.3(2) . . ?
C27 C28 C23 122.5(2) . . ?
C26 C25 C24 123.2(2) . . ?
C2 C3 C4 120.1(2) . . ?
C4 C5 N1 123.3(2) . . ?
C17 C16 C12 117.3(2) . . ?
O1 C14 C12 124.5(2) . . ?
O1 C14 C15 127.5(2) . . ?
C15 C14 C12 108.0(2) . . ?
C6 C2 C1 118.7(2) . . ?
C3 C2 C6 118.4(2) . . ?
C3 C2 C1 123.0(2) . . ?
C14 C15 C10 115.4(2) . . ?
C22 C17 C16 120.9(3) . . ?
C18 C17 C16 121.3(3) . . ?
C18 C17 C22 117.7(3) . . ?
C25 C26 C27 119.6(2) . . ?
C28 C27 C26 118.9(2) . . ?
C5 C4 C3 120.5(2) . . ?
C21 C22 C17 121.0(3) . . ?
C17 C18 C19 120.9(3) . . ?
C21 C20 C19 119.2(3) . . ?
C20 C21 C22 120.8(3) . . ?
C20 C19 C18 120.4(4) . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.153 0.019 0.091 23.7 0.0 ?
2 -0.153 -0.019 0.909 23.7 0.0 ?

_olex2_submission_special_instructions 'No special instructions were received'
