# Electronic Supplementary Material (ESI) for Materials 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_py_cy_0m
_database_code_depnum_ccdc_archive 'CCDC 1900159'
loop_
_audit_author_name
_audit_author_address
'Xing Su'
;Jilin University
China
;
_audit_update_record             
;
2019-02-28 deposited with the CCDC.	2023-06-13 downloaded from the CCDC.
;
_audit_creation_date             2018-06-11
_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         'C36 H26 N2 O'
_chemical_formula_sum            'C36 H26 N2 O'
_chemical_formula_weight         502.59
_chemical_absolute_configuration R
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.9020(5)
_cell_length_b                   14.4344(9)
_cell_length_c                   18.7537(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2680.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9959
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      27.489
_cell_measurement_theta_min      2.822
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.996
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6780
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            32303
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.468
_diffrn_reflns_theta_min         2.721
_diffrn_ambient_temperature      299.73
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.780
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4526
_reflns_number_total             6142
_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       'SAINT V8.38A (?, 2016)'
_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         0.119
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 
;
 Flack x determined using 1593 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         6142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0458
_refine_ls_restrained_S_all      1.036
_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)+(0.0384P)²+0.5243P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.1074
_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:
 C4(H4), C6(H6), C7(H7), C10(H10), C11(H11), C13(H13), C15(H15), C16(H16),
 C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C30(H30), C31(H31), C33(H33),
  C34(H34)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_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 0.2689(2) 0.57607(13) 0.34373(11) 0.0614(6) Uani 1 1 d . . . . .
N1 N 0.4704(3) 0.64479(18) 0.38188(14) 0.0608(7) Uani 1 1 d . . . . .
N2 N 0.0838(4) 0.1769(2) 0.19068(18) 0.0897(10) Uani 1 1 d . . . . .
C1 C 0.3610(3) 0.5856(2) 0.40534(16) 0.0536(7) Uani 1 1 d . . . . .
C2 C 0.2843(3) 0.64677(19) 0.46072(15) 0.0498(6) Uani 1 1 d . . . . .
C3 C 0.3164(3) 0.74280(19) 0.43251(14) 0.0485(7) Uani 1 1 d . . . . .
C4 C 0.2588(3) 0.8270(2) 0.44736(15) 0.0533(7) Uani 1 1 d . . . . .
H4 H 0.187394 0.830583 0.479457 0.064 Uiso 1 1 calc R . . . .
C5 C 0.3068(3) 0.9077(2) 0.41451(15) 0.0553(7) Uani 1 1 d . . . . .
C6 C 0.4134(4) 0.8994(2) 0.36692(18) 0.0660(9) Uani 1 1 d . . . . .
H6 H 0.444548 0.952223 0.343724 0.079 Uiso 1 1 calc R . . . .
C7 C 0.4755(3) 0.8149(2) 0.35268(17) 0.0675(9) Uani 1 1 d . . . . .
H7 H 0.548495 0.811226 0.321607 0.081 Uiso 1 1 calc R . . . .
C8 C 0.4257(3) 0.7367(2) 0.38598(16) 0.0538(7) Uani 1 1 d . . . . .
C9 C 0.5556(4) 0.6150(3) 0.3230(2) 0.0856(11) Uani 1 1 d . . . . .
H9A H 0.574475 0.550007 0.327580 0.128 Uiso 1 1 calc GR . . . .
H9B H 0.638822 0.649119 0.323828 0.128 Uiso 1 1 calc GR . . . .
H9C H 0.509871 0.626125 0.278674 0.128 Uiso 1 1 calc GR . . . .
C10 C 0.4090(3) 0.4935(2) 0.43109(18) 0.0642(8) Uani 1 1 d . . . . .
H10 H 0.466751 0.492276 0.470171 0.077 Uiso 1 1 calc R . . . .
C11 C 0.3748(3) 0.4141(2) 0.40202(18) 0.0623(8) Uani 1 1 d . . . . .
H11 H 0.407497 0.359262 0.421464 0.075 Uiso 1 1 calc R . . . .
C12 C 0.2874(3) 0.41031(19) 0.34055(15) 0.0489(6) Uani 1 1 d . . . . .
C13 C 0.2487(3) 0.3288(2) 0.30652(16) 0.0547(7) Uani 1 1 d . . . . .
H13 H 0.281288 0.272359 0.323046 0.066 Uiso 1 1 calc R . . . .
C14 C 0.1625(3) 0.3306(2) 0.24851(15) 0.0532(7) Uani 1 1 d . . . . .
C15 C 0.1136(3) 0.4146(2) 0.22331(15) 0.0532(7) Uani 1 1 d . . . . .
H15 H 0.055094 0.415588 0.184534 0.064 Uiso 1 1 calc R . . . .
C16 C 0.1511(3) 0.4961(2) 0.25521(14) 0.0518(7) Uani 1 1 d . . . . .
H16 H 0.119481 0.552411 0.237790 0.062 Uiso 1 1 calc R . . . .
C17 C 0.2371(3) 0.49379(18) 0.31397(13) 0.0453(6) Uani 1 1 d . . . . .
C18 C 0.1189(4) 0.2449(2) 0.21612(18) 0.0652(8) Uani 1 1 d . . . . .
C19 C 0.1335(3) 0.6247(2) 0.46375(19) 0.0635(8) Uani 1 1 d . . . . .
H19A H 0.094118 0.634262 0.417541 0.095 Uiso 1 1 calc GR . . . .
H19B H 0.090434 0.664757 0.497747 0.095 Uiso 1 1 calc GR . . . .
H19C H 0.121078 0.561384 0.477862 0.095 Uiso 1 1 calc GR . . . .
C20 C 0.3455(4) 0.6362(2) 0.53557(17) 0.0708(9) Uani 1 1 d . . . . .
H20A H 0.328239 0.574838 0.553054 0.106 Uiso 1 1 calc GR . . . .
H20B H 0.305232 0.680723 0.567135 0.106 Uiso 1 1 calc GR . . . .
H20C H 0.441144 0.646517 0.533301 0.106 Uiso 1 1 calc GR . . . .
C21 C 0.2435(3) 0.9997(2) 0.42850(15) 0.0557(7) Uani 1 1 d . . . . .
C22 C 0.2530(3) 1.04246(17) 0.49574(14) 0.0440(6) Uani 1 1 d . . . . .
C23 C 0.3226(3) 1.00066(19) 0.55503(15) 0.0493(6) Uani 1 1 d . . . . .
H23 H 0.362007 0.942663 0.549206 0.059 Uiso 1 1 calc R . . . .
C24 C 0.3321(3) 1.0434(2) 0.61872(15) 0.0531(7) Uani 1 1 d . . . . .
H24 H 0.377187 1.013998 0.655852 0.064 Uiso 1 1 calc R . . . .
C25 C 0.2747(3) 1.13279(19) 0.63055(15) 0.0514(7) Uani 1 1 d . . . . .
C26 C 0.2852(4) 1.1781(2) 0.69632(18) 0.0687(9) Uani 1 1 d . . . . .
H26 H 0.328801 1.149237 0.734174 0.082 Uiso 1 1 calc R . . . .
C27 C 0.2311(5) 1.2655(3) 0.7053(2) 0.0873(12) Uani 1 1 d . . . . .
H27 H 0.238984 1.295104 0.749141 0.105 Uiso 1 1 calc R . . . .
C28 C 0.1659(4) 1.3090(3) 0.6502(2) 0.0862(12) Uani 1 1 d . . . . .
H28 H 0.131034 1.368191 0.657158 0.103 Uiso 1 1 calc R . . . .
C29 C 0.1508(3) 1.2666(2) 0.5841(2) 0.0642(9) Uani 1 1 d . . . . .
C30 C 0.0794(4) 1.3084(3) 0.5261(3) 0.0821(11) Uani 1 1 d . . . . .
H30 H 0.042583 1.367171 0.531979 0.098 Uiso 1 1 calc R . . . .
C31 C 0.0645(3) 1.2652(2) 0.4639(2) 0.0761(11) Uani 1 1 d . . . . .
H31 H 0.015519 1.294041 0.427863 0.091 Uiso 1 1 calc R . . . .
C32 C 0.1219(3) 1.1755(2) 0.45070(18) 0.0596(8) Uani 1 1 d . . . . .
C33 C 0.1114(4) 1.1301(2) 0.3859(2) 0.0776(11) Uani 1 1 d . . . . .
H33 H 0.062386 1.157301 0.349167 0.093 Uiso 1 1 calc R . . . .
C34 C 0.1722(4) 1.0456(2) 0.37486(18) 0.0726(10) Uani 1 1 d . . . . .
H34 H 0.165503 1.018124 0.330139 0.087 Uiso 1 1 calc R . . . .
C35 C 0.1944(3) 1.13170(18) 0.50676(15) 0.0460(6) Uani 1 1 d . . . . .
C36 C 0.2065(3) 1.17734(18) 0.57355(15) 0.0469(6) Uani 1 1 d . . . . .


_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 C1 1.478(3) . ?
O1 C17 1.350(3) . ?
N1 C1 1.448(4) . ?
N1 C8 1.401(4) . ?
N1 C9 1.456(4) . ?
N2 C18 1.145(4) . ?
C1 C2 1.560(4) . ?
C1 C10 1.492(4) . ?
C2 C3 1.517(4) . ?
C2 C19 1.528(4) . ?
C2 C20 1.537(4) . ?
C3 C4 1.372(4) . ?
C3 C8 1.393(4) . ?
C4 C5 1.401(4) . ?
C5 C6 1.388(4) . ?
C5 C21 1.491(4) . ?
C6 C7 1.392(5) . ?
C7 C8 1.381(4) . ?
C10 C11 1.314(4) . ?
C11 C12 1.442(4) . ?
C12 C13 1.392(4) . ?
C12 C17 1.396(4) . ?
C13 C14 1.383(4) . ?
C14 C15 1.389(4) . ?
C14 C18 1.443(4) . ?
C15 C16 1.371(4) . ?
C16 C17 1.393(4) . ?
C21 C22 1.407(4) . ?
C21 C34 1.396(4) . ?
C22 C23 1.440(4) . ?
C22 C35 1.428(4) . ?
C23 C24 1.348(4) . ?
C24 C25 1.427(4) . ?
C25 C26 1.400(4) . ?
C25 C36 1.418(4) . ?
C26 C27 1.380(5) . ?
C27 C28 1.371(6) . ?
C28 C29 1.390(5) . ?
C29 C30 1.432(5) . ?
C29 C36 1.415(4) . ?
C30 C31 1.331(5) . ?
C31 C32 1.436(5) . ?
C32 C33 1.384(5) . ?
C32 C35 1.422(4) . ?
C33 C34 1.376(5) . ?
C35 C36 1.420(4) . ?

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 O1 C1 123.3(2) . . ?
C1 N1 C9 119.4(3) . . ?
C8 N1 C1 107.8(2) . . ?
C8 N1 C9 120.3(3) . . ?
O1 C1 C2 105.8(2) . . ?
O1 C1 C10 111.5(2) . . ?
N1 C1 O1 106.2(2) . . ?
N1 C1 C2 103.5(2) . . ?
N1 C1 C10 112.7(2) . . ?
C10 C1 C2 116.3(3) . . ?
C3 C2 C1 100.5(2) . . ?
C3 C2 C19 114.1(2) . . ?
C3 C2 C20 109.0(2) . . ?
C19 C2 C1 112.5(2) . . ?
C19 C2 C20 109.3(3) . . ?
C20 C2 C1 111.1(2) . . ?
C4 C3 C2 130.7(3) . . ?
C4 C3 C8 120.4(3) . . ?
C8 C3 C2 108.9(2) . . ?
C3 C4 C5 120.4(3) . . ?
C4 C5 C21 121.3(3) . . ?
C6 C5 C4 118.0(3) . . ?
C6 C5 C21 120.7(3) . . ?
C5 C6 C7 122.3(3) . . ?
C8 C7 C6 118.2(3) . . ?
C3 C8 N1 109.8(3) . . ?
C7 C8 N1 129.5(3) . . ?
C7 C8 C3 120.6(3) . . ?
C11 C10 C1 124.1(3) . . ?
C10 C11 C12 121.3(3) . . ?
C13 C12 C11 124.3(3) . . ?
C13 C12 C17 117.9(3) . . ?
C17 C12 C11 117.8(3) . . ?
C14 C13 C12 121.0(3) . . ?
C13 C14 C15 119.9(3) . . ?
C13 C14 C18 120.0(3) . . ?
C15 C14 C18 120.1(3) . . ?
C16 C15 C14 120.4(3) . . ?
C15 C16 C17 119.3(3) . . ?
O1 C17 C12 121.9(2) . . ?
O1 C17 C16 116.6(2) . . ?
C16 C17 C12 121.4(2) . . ?
N2 C18 C14 179.6(4) . . ?
C22 C21 C5 121.3(3) . . ?
C34 C21 C5 120.5(3) . . ?
C34 C21 C22 118.1(3) . . ?
C21 C22 C23 122.7(3) . . ?
C21 C22 C35 119.9(2) . . ?
C35 C22 C23 117.4(2) . . ?
C24 C23 C22 121.7(3) . . ?
C23 C24 C25 121.6(3) . . ?
C26 C25 C24 122.0(3) . . ?
C26 C25 C36 119.1(3) . . ?
C36 C25 C24 118.8(3) . . ?
C27 C26 C25 120.4(4) . . ?
C28 C27 C26 120.6(4) . . ?
C27 C28 C29 121.3(3) . . ?
C28 C29 C30 123.0(3) . . ?
C28 C29 C36 119.0(3) . . ?
C36 C29 C30 118.0(3) . . ?
C31 C30 C29 121.6(3) . . ?
C30 C31 C32 122.0(3) . . ?
C33 C32 C31 123.3(3) . . ?
C33 C32 C35 118.5(3) . . ?
C35 C32 C31 118.3(3) . . ?
C34 C33 C32 121.3(3) . . ?
C33 C34 C21 122.2(3) . . ?
C32 C35 C22 120.0(3) . . ?
C36 C35 C22 120.8(2) . . ?
C36 C35 C32 119.2(2) . . ?
C25 C36 C35 119.6(2) . . ?
C29 C36 C25 119.5(3) . . ?
C29 C36 C35 120.9(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
