# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_2a
_database_code_depnum_ccdc_archive 'CCDC 1947196'
loop_
_audit_author_name
_audit_author_address
'Yulia Nelyubina'
;AN Nesmeyanov Institute of Organoelement Compounds
Russia
;
_audit_update_record             
;
2019-08-14 deposited with the CCDC.	2019-12-06 downloaded from the CCDC.
;
_audit_creation_date             2019-08-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         'C30 H20 N2 O2, 2(C H4 O)'
_chemical_formula_sum            'C32 H28 N2 O4'
_chemical_formula_weight         504.59
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   8.9151(10)
_cell_length_b                   9.6712(11)
_cell_length_c                   15.8118(17)
_cell_angle_alpha                72.760(3)
_cell_angle_beta                 83.325(3)
_cell_angle_gamma                76.504(3)
_cell_volume                     1264.5(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1524
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      3
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9932
_exptl_absorpt_correction_T_min  0.9771
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1998a)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3252
_exptl_crystal_description       prism
_exptl_crystal_F_000             532.2604
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_av_unetI/netI     0.1498
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14904
_diffrn_reflns_theta_full        25.9994
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.26
_diffrn_ambient_temperature      120.15
_diffrn_measured_fraction_theta_full 0.9996
_diffrn_measured_fraction_theta_max 0.9996
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area detector'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                2543
_reflns_number_total             4953
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.7870
_refine_diff_density_min         -0.5753
_refine_diff_density_rms         0.0974
_refine_ls_d_res_high            0.8107
_refine_ls_d_res_low             9.0313
_refine_ls_goodness_of_fit_ref   0.8751
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    59
_refine_ls_number_parameters     356
_refine_ls_number_reflns         4953
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1100
_refine_ls_R_factor_gt           0.0592
_refine_ls_restrained_S_all      0.8749
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0901P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1406
_refine_ls_wR_factor_ref         0.1645
_olex2_refinement_description    
;
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
_atom_site_disorder_group
N1 N 0.2289(2) 1.0022(2) 0.57241(14) 0.0245(5) Uani 1.000000 . .
H1 H 0.1704(2) 0.9767(2) 0.63014(14) 0.0294(6) Uiso 1.000000 R .
C2 C 0.2403(3) 0.9382(3) 0.50566(16) 0.0219(6) Uani 1.000000 . .
C3 C 0.1975(3) 0.8070(3) 0.50570(17) 0.0233(6) Uani 1.000000 . .
C4 C 0.2173(3) 0.7765(3) 0.42484(17) 0.0240(6) Uani 1.000000 . .
H4 H 0.1915(3) 0.6883(3) 0.42166(17) 0.0288(7) Uiso 1.000000 R .
N5 N 0.2720(2) 0.8659(2) 0.34882(13) 0.0227(5) Uani 1.000000 . .
C6 C 0.3153(3) 0.9915(3) 0.34808(17) 0.0232(6) Uani 1.000000 . .
C7 C 0.3036(3) 1.0270(3) 0.42730(17) 0.0228(6) Uani 1.000000 . .
C8 C 0.3340(3) 1.1520(3) 0.44974(17) 0.0247(6) Uani 1.000000 . .
C9 C 0.2833(3) 1.1330(3) 0.53927(17) 0.0247(6) Uani 1.000000 . .
C10 C 0.2873(3) 1.2364(3) 0.58393(18) 0.0272(6) Uani 1.000000 . .
H10 H 0.2518(3) 1.2231(3) 0.64426(18) 0.0326(8) Uiso 1.000000 R .
C11 C 0.3453(3) 1.3593(3) 0.53625(19) 0.0302(7) Uani 1.000000 . .
H11 H 0.3493(3) 1.4324(3) 0.56447(19) 0.0363(8) Uiso 1.000000 R .
C12 C 0.3979(3) 1.3786(3) 0.44807(19) 0.0308(7) Uani 1.000000 . .
H12 H 0.4387(3) 1.4635(3) 0.41781(19) 0.0369(8) Uiso 1.000000 R .
C13 C 0.3920(3) 1.2773(3) 0.40358(19) 0.0274(6) Uani 1.000000 . .
H13 H 0.4265(3) 1.2924(3) 0.34302(19) 0.0328(8) Uiso 1.000000 R .
C14 C 0.1430(3) 0.7025(3) 0.58542(17) 0.0235(6) Uani 1.000000 . .
C15 C 0.2101(3) 0.6716(3) 0.66672(17) 0.0279(6) Uani 1.000000 . .
H15 H 0.2866(3) 0.7227(3) 0.67115(17) 0.0335(8) Uiso 1.000000 R .
C16 C 0.1658(3) 0.5676(3) 0.74044(18) 0.0334(7) Uani 1.000000 . .
H16 H 0.2127(3) 0.5471(3) 0.79502(18) 0.0401(8) Uiso 1.000000 R .
C17 C 0.0536(3) 0.4931(3) 0.73528(19) 0.0328(7) Uani 1.000000 . .
H17 H 0.0236(3) 0.4216(3) 0.78608(19) 0.0393(8) Uiso 1.000000 R .
C18 C -0.0145(3) 0.5234(3) 0.65575(18) 0.0309(7) Uani 1.000000 . .
H18 H -0.0916(3) 0.4727(3) 0.65192(18) 0.0371(8) Uiso 1.000000 R .
C19 C 0.0293(3) 0.6274(3) 0.58181(18) 0.0269(6) Uani 1.000000 . .
H19 H -0.0190(3) 0.6480(3) 0.52766(18) 0.0323(8) Uiso 1.000000 R .
C20 C 0.2807(3) 0.8212(3) 0.26796(17) 0.0240(6) Uani 1.000000 . .
C21 C 0.4220(3) 0.7458(3) 0.24202(18) 0.0297(7) Uani 1.000000 . .
H21 H 0.5103(3) 0.7289(3) 0.27502(18) 0.0356(8) Uiso 1.000000 R .
C22 C 0.4342(3) 0.6952(3) 0.16789(19) 0.0346(7) Uani 1.000000 . .
H22 H 0.5312(3) 0.6441(3) 0.14959(19) 0.0415(9) Uiso 1.000000 R .
C23 C 0.3063(3) 0.7187(3) 0.12066(18) 0.0323(7) Uani 1.000000 . .
H23 H 0.3141(3) 0.6828(3) 0.07015(18) 0.0387(8) Uiso 1.000000 R .
C24 C 0.1659(3) 0.7950(3) 0.14719(17) 0.0269(6) Uani 1.000000 . .
H24 H 0.0786(3) 0.8122(3) 0.11342(17) 0.0323(8) Uiso 1.000000 R .
C25 C 0.1482(3) 0.8473(3) 0.22139(17) 0.0244(6) Uani 1.000000 . .
C26 C 0.3637(3) 1.0937(3) 0.26420(17) 0.0246(6) Uani 1.000000 . .
C27 C 0.2529(3) 1.2113(3) 0.22005(18) 0.0317(7) Uani 1.000000 . .
H27 H 0.1470(3) 1.2176(3) 0.23887(18) 0.0381(8) Uiso 1.000000 R .
C28 C 0.2969(3) 1.3199(3) 0.14833(19) 0.0380(8) Uani 1.000000 . .
H28 H 0.2213(3) 1.4009(3) 0.11809(19) 0.0456(9) Uiso 1.000000 R .
C29 C 0.4509(4) 1.3099(3) 0.12108(19) 0.0390(8) Uani 1.000000 . .
H29 H 0.4811(4) 1.3841(3) 0.07194(19) 0.0469(9) Uiso 1.000000 R .
C30 C 0.5614(4) 1.1926(3) 0.1648(2) 0.0399(8) Uani 1.000000 . .
H30 H 0.6673(4) 1.1863(3) 0.1459(2) 0.0479(9) Uiso 1.000000 R .
C31 C 0.5176(3) 1.0847(3) 0.23608(19) 0.0336(7) Uani 1.000000 . .
H31 H 0.5935(3) 1.0038(3) 0.26602(19) 0.0403(8) Uiso 1.000000 R .
C32 C -0.0088(3) 0.9291(3) 0.24731(18) 0.0277(6) Uani 1.000000 . .
O33 O -0.1247(2) 0.9086(2) 0.21806(13) 0.0409(5) Uani 1.000000 . .
O34 O -0.0135(2) 1.0095(2) 0.29745(12) 0.0319(5) Uani 1.000000 . .
C1S C 0.6926(4) 0.9077(4) 0.0420(2) 0.0551(10) Uani 1.000000 . .
O1S O 0.7752(2) 0.7885(2) 0.10668(14) 0.0463(6) Uani 1.000000 . .
H1S H 0.8205(2) 0.8249(2) 0.14875(14) 0.0556(7) Uiso 1.000000 R .
C2S C 1.0494(5) 0.7198(5) -0.0540(2) 0.0824(14) Uani 1.000000 D .
O2S O 0.9870(5) 0.6162(5) 0.0242(3) 0.0491(17) Uani 0.501(5) D 1
H2S H 0.9131(5) 0.6816(5) 0.0491(3) 0.059(2) Uiso 0.501(5) R 1
O2S' O 1.1819(5) 0.6014(5) -0.0367(3) 0.0527(17) Uani 0.499(5) D 2
H2S' H 1.1190(5) 0.5306(5) -0.0245(3) 0.063(2) Uiso 0.499(5) R 2
H1Sa H 0.666(2) 0.8709(5) -0.0046(8) 0.0827(15) Uiso 1.000000 GR .
H1Sb H 0.5977(13) 0.9538(16) 0.0698(4) 0.0827(15) Uiso 1.000000 GR .
H1Sc H 0.7566(10) 0.9811(12) 0.0160(10) 0.0827(15) Uiso 1.000000 GR .
H2Sa H 0.974(3) 0.758(5) -0.1001(16) 0.124(2) Uiso 0.501(5) GR 1
H2Sb H 1.070(7) 0.802(4) -0.0364(9) 0.124(2) Uiso 0.501(5) GR 1
H2Sc H 1.146(4) 0.6673(17) -0.077(2) 0.124(2) Uiso 0.501(5) GR 1
H2Sd H 1.014(4) 0.734(4) -0.1130(17) 0.124(2) Uiso 0.499(5) GR 2
H2Se H 0.967(2) 0.696(3) -0.009(2) 0.124(2) Uiso 0.499(5) GR 2
H2Sf H 1.0764(19) 0.8112(15) -0.052(4) 0.124(2) Uiso 0.499(5) GR 2


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 H1 0.9907 . ?
N1 C2 1.357(3) . ?
N1 C9 1.395(3) . ?
C2 C3 1.407(3) . ?
C2 C7 1.422(3) . ?
C3 C4 1.378(3) . ?
C3 C14 1.476(4) . ?
C4 H4 0.9500 . ?
C4 N5 1.369(3) . ?
N5 C6 1.354(3) . ?
N5 C20 1.455(3) . ?
C6 C7 1.380(3) . ?
C6 C26 1.487(3) . ?
C7 C8 1.446(3) . ?
C8 C9 1.407(4) . ?
C8 C13 1.396(4) . ?
C9 C10 1.393(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.384(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.390(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.377(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.402(3) . ?
C14 C19 1.393(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.382(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.384(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.383(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.382(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.384(4) . ?
C20 C25 1.397(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.382(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.373(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.385(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.389(3) . ?
C25 C32 1.515(4) . ?
C26 C27 1.386(4) . ?
C26 C31 1.383(4) . ?
C27 H27 0.9500 . ?
C27 C28 1.388(4) . ?
C28 H28 0.9500 . ?
C28 C29 1.380(4) . ?
C29 H29 0.9500 . ?
C29 C30 1.381(4) . ?
C30 H30 0.9500 . ?
C30 C31 1.379(4) . ?
C31 H31 0.9500 . ?
C32 O33 1.258(3) . ?
C32 O34 1.256(3) . ?
C1S O1S 1.413(4) . ?
C1S H1Sa 0.9800 . ?
C1S H1Sb 0.9800 . ?
C1S H1Sc 0.9800 . ?
O1S H1S 0.9986 . ?
C2S O2S 1.486(3) . ?
C2S O2S' 1.428(3) . ?
C2S H2Sa 0.9800 . ?
C2S H2Sb 0.9800 . ?
C2S H2Sc 0.9800 . ?
C2S H2Sd 0.9800 . ?
C2S H2Se 0.9800 . ?
C2S H2Sf 0.9800 . ?
O2S H2S 0.9386 . ?
O2S' H2S' 0.9475 . ?

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
C2 N1 H1 127.1 . . ?
C9 N1 H1 123.41(14) . . ?
C9 N1 C2 108.0(2) . . ?
C3 C2 N1 129.5(2) . . ?
C7 C2 N1 109.6(2) . . ?
C7 C2 C3 120.9(2) . . ?
C4 C3 C2 114.9(2) . . ?
C14 C3 C2 124.4(2) . . ?
C14 C3 C4 120.6(2) . . ?
H4 C4 C3 118.10(15) . . ?
N5 C4 C3 123.8(2) . . ?
N5 C4 H4 118.10(14) . . ?
C6 N5 C4 121.9(2) . . ?
C20 N5 C4 117.2(2) . . ?
C20 N5 C6 121.0(2) . . ?
C7 C6 N5 117.7(2) . . ?
C26 C6 N5 121.5(2) . . ?
C26 C6 C7 120.6(2) . . ?
C6 C7 C2 120.7(2) . . ?
C8 C7 C2 106.8(2) . . ?
C8 C7 C6 132.3(2) . . ?
C9 C8 C7 105.2(2) . . ?
C13 C8 C7 135.2(2) . . ?
C13 C8 C9 119.5(2) . . ?
C8 C9 N1 110.3(2) . . ?
C10 C9 N1 127.5(2) . . ?
C10 C9 C8 122.2(2) . . ?
H10 C10 C9 121.58(16) . . ?
C11 C10 C9 116.8(3) . . ?
C11 C10 H10 121.58(16) . . ?
H11 C11 C10 119.18(16) . . ?
C12 C11 C10 121.6(3) . . ?
C12 C11 H11 119.18(16) . . ?
H12 C12 C11 119.25(16) . . ?
C13 C12 C11 121.5(3) . . ?
C13 C12 H12 119.25(17) . . ?
C12 C13 C8 118.3(3) . . ?
H13 C13 C8 120.84(15) . . ?
H13 C13 C12 120.84(17) . . ?
C15 C14 C3 120.2(2) . . ?
C19 C14 C3 121.6(2) . . ?
C19 C14 C15 118.1(2) . . ?
H15 C15 C14 119.71(15) . . ?
C16 C15 C14 120.6(3) . . ?
C16 C15 H15 119.71(16) . . ?
H16 C16 C15 119.78(16) . . ?
C17 C16 C15 120.4(3) . . ?
C17 C16 H16 119.78(17) . . ?
H17 C17 C16 120.19(17) . . ?
C18 C17 C16 119.6(3) . . ?
C18 C17 H17 120.19(17) . . ?
H18 C18 C17 119.90(17) . . ?
C19 C18 C17 120.2(3) . . ?
C19 C18 H18 119.90(16) . . ?
C18 C19 C14 121.1(3) . . ?
H19 C19 C14 119.47(16) . . ?
H19 C19 C18 119.47(16) . . ?
C21 C20 N5 117.6(2) . . ?
C25 C20 N5 120.5(2) . . ?
C25 C20 C21 121.8(2) . . ?
H21 C21 C20 120.16(15) . . ?
C22 C21 C20 119.7(3) . . ?
C22 C21 H21 120.16(16) . . ?
H22 C22 C21 119.94(16) . . ?
C23 C22 C21 120.1(3) . . ?
C23 C22 H22 119.94(17) . . ?
H23 C23 C22 120.25(17) . . ?
C24 C23 C22 119.5(3) . . ?
C24 C23 H23 120.25(16) . . ?
H24 C24 C23 118.82(16) . . ?
C25 C24 C23 122.4(3) . . ?
C25 C24 H24 118.82(15) . . ?
C24 C25 C20 116.6(2) . . ?
C32 C25 C20 123.6(2) . . ?
C32 C25 C24 119.8(2) . . ?
C27 C26 C6 118.3(2) . . ?
C31 C26 C6 121.5(2) . . ?
C31 C26 C27 119.7(3) . . ?
H27 C27 C26 120.03(16) . . ?
C28 C27 C26 119.9(3) . . ?
C28 C27 H27 120.03(17) . . ?
H28 C28 C27 120.12(17) . . ?
C29 C28 C27 119.8(3) . . ?
C29 C28 H28 120.12(17) . . ?
H29 C29 C28 119.80(17) . . ?
C30 C29 C28 120.4(3) . . ?
C30 C29 H29 119.80(17) . . ?
H30 C30 C29 120.09(17) . . ?
C31 C30 C29 119.8(3) . . ?
C31 C30 H30 120.09(17) . . ?
C30 C31 C26 120.4(3) . . ?
H31 C31 C26 119.82(16) . . ?
H31 C31 C30 119.82(17) . . ?
O33 C32 C25 117.1(2) . . ?
O34 C32 C25 117.8(2) . . ?
O34 C32 O33 125.1(3) . . ?
H1Sa C1S O1S 109.5 . . ?
H1Sb C1S O1S 109.5 . . ?
H1Sb C1S H1Sa 109.5 . . ?
H1Sc C1S O1S 109.5 . . ?
H1Sc C1S H1Sa 109.5 . . ?
H1Sc C1S H1Sb 109.5 . . ?
H1S O1S C1S 111.1 . . ?
H2Sa C2S O2S 109.5 . . ?
H2Sb C2S O2S 109.5 . . ?
H2Sb C2S H2Sa 109.5 . . ?
H2Sc C2S O2S 109.5 . . ?
H2Sc C2S H2Sa 109.5 . . ?
H2Sc C2S H2Sb 109.5 . . ?
H2Sd C2S O2S' 109.5 . . ?
H2Se C2S O2S' 109.5 . . ?
H2Se C2S H2Sd 109.5 . . ?
H2Sf C2S O2S' 109.5 . . ?
H2Sf C2S H2Sd 109.5 . . ?
H2Sf C2S H2Se 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_restr_equal_distance_atom_site_label_1
_restr_equal_distance_atom_site_label_2
_restr_equal_distance_site_symmetry_2
_restr_equal_distance_class_id
C2S O2S 1 1
C2S O2S' 1 1

loop_
_restr_equal_distance_class_class_id
_restr_equal_distance_class_target_weight_param
_restr_equal_distance_class_average
_restr_equal_distance_class_esd
_restr_equal_distance_class_diff_max
1 0.0020 1.4570 0.0289 0.0289

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1947197'
loop_
_audit_author_name
_audit_author_address
'Yulia Nelyubina'
;AN Nesmeyanov Institute of Organoelement Compounds
Russia
;
_audit_update_record             
;
2019-08-14 deposited with the CCDC.	2019-12-06 downloaded from the CCDC.
;
_audit_creation_date             2019-08-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         'C30 H22 N2 O3'
_chemical_formula_sum            'C30 H22 N2 O3'
_chemical_formula_weight         458.52
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           ' P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z

_symmetry_Int_Tables_number      4
_cell_length_a                   11.3360(8)
_cell_length_b                   6.3863(4)
_cell_length_c                   15.8956(11)
_cell_angle_alpha                90
_cell_angle_beta                 95.678(2)
_cell_angle_gamma                90
_cell_volume                     1145.12(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3306
_cell_measurement_temperature    120
_cell_measurement_theta_max      30
_cell_measurement_theta_min      3
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'APEX2 (Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3297
_exptl_crystal_description       prism
_exptl_crystal_F_000             480.2284
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_av_unetI/netI     0.1071
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13219
_diffrn_reflns_theta_full        28.9999
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         1.29
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.9836
_diffrn_measured_fraction_theta_max 0.9836
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.973
_reflns_limit_h_max              15
_reflns_limit_h_min              -15
_reflns_limit_k_max              8
_reflns_limit_k_min              -8
_reflns_limit_l_max              21
_reflns_limit_l_min              -21
_reflns_number_gt                4389
_reflns_number_total             6010
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.3656
_refine_diff_density_min         -0.3602
_refine_diff_density_rms         0.0829
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.2(16)
_refine_ls_d_res_high            0.7330
_refine_ls_d_res_low             15.8176
_refine_ls_goodness_of_fit_ref   1.0335
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    44
_refine_ls_number_parameters     316
_refine_ls_number_reflns         6010
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0521
_refine_ls_restrained_S_all      1.0335
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0287P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.1016
_olex2_refinement_description    
;
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
N1 N 0.73700(16) 0.3446(3) 0.15607(11) 0.0156(4) Uani 1.000000 .
C2 C 0.77365(18) 0.4086(3) 0.24400(13) 0.0147(5) Uani 1.000000 .
H2 H 0.80840(18) 0.5524(3) 0.24297(13) 0.0176(5) Uiso 1.000000 R
C3 C 0.65393(18) 0.4226(3) 0.28528(12) 0.0122(4) Uani 1.000000 .
N4 N 0.62352(15) 0.2348(3) 0.32989(10) 0.0147(4) Uani 1.000000 .
H4 H 0.64375(15) 0.1005(3) 0.31043(10) 0.0177(5) Uiso 1.000000 R
C5 C 0.63480(17) 0.2728(3) 0.41574(13) 0.0134(4) Uani 1.000000 .
C6 C 0.62222(18) 0.1282(3) 0.48002(13) 0.0156(5) Uani 1.000000 .
H6 H 0.60604(18) -0.0151(3) 0.46777(13) 0.0187(6) Uiso 1.000000 R
C7 C 0.63422(19) 0.2016(4) 0.56224(14) 0.0190(5) Uani 1.000000 .
H7 H 0.62558(19) 0.1061(4) 0.60704(14) 0.0228(6) Uiso 1.000000 R
C8 C 0.65874(19) 0.4125(4) 0.58174(13) 0.0179(5) Uani 1.000000 .
H8 H 0.66702(19) 0.4570(4) 0.63905(13) 0.0214(6) Uiso 1.000000 R
C9 C 0.67086(19) 0.5553(4) 0.51819(13) 0.0171(5) Uani 1.000000 .
H9 H 0.68726(19) 0.6984(4) 0.53090(13) 0.0205(6) Uiso 1.000000 R
C10 C 0.65842(18) 0.4845(3) 0.43446(13) 0.0130(4) Uani 1.000000 .
C11 C 0.66461(18) 0.5930(3) 0.35521(13) 0.0145(5) Uani 1.000000 .
C12 C 0.78363(19) 0.4593(3) 0.09209(13) 0.0161(5) Uani 1.000000 .
C13 C 0.90132(19) 0.5229(4) 0.09119(14) 0.0192(5) Uani 1.000000 .
H13 H 0.95914(19) 0.4918(4) 0.13688(14) 0.0231(6) Uiso 1.000000 R
C14 C 0.9306(2) 0.6334(4) 0.02106(14) 0.0238(6) Uani 1.000000 .
H14 H 1.0102(2) 0.6779(4) 0.01882(14) 0.0286(7) Uiso 1.000000 R
C15 C 0.84606(19) 0.6810(4) -0.04656(15) 0.0249(6) Uani 1.000000 .
H15 H 0.86926(19) 0.7552(4) -0.09406(15) 0.0299(7) Uiso 1.000000 R
C16 C 0.7295(2) 0.6213(4) -0.04475(14) 0.0197(5) Uani 1.000000 .
H16 H 0.6718(2) 0.6541(4) -0.09033(14) 0.0236(6) Uiso 1.000000 R
C17 C 0.69821(18) 0.5113(3) 0.02588(13) 0.0157(5) Uani 1.000000 .
C18 C 0.58414(19) 0.4367(3) 0.04791(13) 0.0142(4) Uani 1.000000 .
C19 C 0.60611(18) 0.3437(3) 0.13848(13) 0.0140(5) Uani 1.000000 .
C20 C 0.56693(18) 0.4861(3) 0.20824(12) 0.0133(5) Uani 1.000000 .
H20 H 0.58958(18) 0.6315(3) 0.19299(12) 0.0160(5) Uiso 1.000000 R
C21 C 0.86515(18) 0.2645(4) 0.28958(13) 0.0160(5) Uani 1.000000 .
C22 C 0.8855(2) 0.0660(4) 0.26003(16) 0.0247(6) Uani 1.000000 .
H22 H 0.8439(2) 0.0188(4) 0.20871(16) 0.0296(7) Uiso 1.000000 R
C23 C 0.9663(2) -0.0647(4) 0.30500(18) 0.0320(6) Uani 1.000000 .
H23 H 0.9793(2) -0.2015(4) 0.28438(18) 0.0384(8) Uiso 1.000000 R
C24 C 1.0280(2) 0.0010(4) 0.37904(17) 0.0324(7) Uani 1.000000 .
H24 H 1.0828(2) -0.0902(4) 0.40971(17) 0.0389(8) Uiso 1.000000 R
C25 C 1.0097(2) 0.2007(5) 0.40850(15) 0.0315(6) Uani 1.000000 .
H25 H 1.0528(2) 0.2477(5) 0.45928(15) 0.0378(8) Uiso 1.000000 R
C26 C 0.9290(2) 0.3323(4) 0.36442(15) 0.0246(6) Uani 1.000000 .
H26 H 0.9167(2) 0.4694(4) 0.38504(15) 0.0296(7) Uiso 1.000000 R
O27 O 0.67694(14) 0.7786(2) 0.34010(9) 0.0195(4) Uani 1.000000 .
O28 O 0.48677(13) 0.4370(2) 0.00808(9) 0.0177(3) Uani 1.000000 .
O29 O 0.55807(12) 0.1432(2) 0.14511(9) 0.0161(3) Uani 1.000000 .
H29 H 0.53890(12) 0.0966(2) 0.09292(9) 0.0193(4) Uiso 1.000000 R
C30 C 0.43631(18) 0.4941(3) 0.21974(12) 0.0142(5) Uani 1.000000 .
C31 C 0.37471(18) 0.3233(3) 0.24960(13) 0.0155(5) Uani 1.000000 .
H31 H 0.41473(18) 0.1945(3) 0.26180(13) 0.0186(6) Uiso 1.000000 R
C32 C 0.25554(19) 0.3420(4) 0.26135(13) 0.0196(5) Uani 1.000000 .
H32 H 0.21452(19) 0.2261(4) 0.28205(13) 0.0235(6) Uiso 1.000000 R
C33 C 0.1959(2) 0.5283(4) 0.24314(14) 0.0209(5) Uani 1.000000 .
H33 H 0.1147(2) 0.5408(4) 0.25249(14) 0.0251(6) Uiso 1.000000 R
C34 C 0.25456(19) 0.6960(4) 0.21137(14) 0.0219(5) Uani 1.000000 .
H34 H 0.21314(19) 0.8223(4) 0.19701(14) 0.0262(6) Uiso 1.000000 R
C35 C 0.37412(19) 0.6791(4) 0.20052(13) 0.0193(5) Uani 1.000000 .
H35 H 0.41433(19) 0.7957(4) 0.17963(13) 0.0232(6) Uiso 1.000000 R


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 C2 1.476(3) . ?
N1 C12 1.399(3) . ?
N1 C19 1.483(3) . ?
C2 H2 1.0000 . ?
C2 C3 1.567(3) . ?
C2 C21 1.516(3) . ?
C3 N4 1.452(3) . ?
C3 C11 1.551(3) . ?
C3 C20 1.548(3) . ?
N4 H4 0.9478 . ?
N4 C5 1.379(3) . ?
C5 C6 1.395(3) . ?
C5 C10 1.404(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.382(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.404(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.378(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.400(3) . ?
C10 C11 1.446(3) . ?
C11 O27 1.220(2) . ?
C12 C13 1.396(3) . ?
C12 C17 1.398(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.387(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.401(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.378(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.400(3) . ?
C17 C18 1.453(3) . ?
C18 C19 1.555(3) . ?
C18 O28 1.217(2) . ?
C19 C20 1.533(3) . ?
C19 O29 1.399(2) . ?
C20 H20 1.0000 . ?
C20 C30 1.511(3) . ?
C21 C22 1.380(3) . ?
C21 C26 1.398(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.385(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.374(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.381(4) . ?
C25 H25 0.9500 . ?
C25 C26 1.382(3) . ?
C26 H26 0.9500 . ?
O29 H29 0.8878 . ?
C30 C31 1.403(3) . ?
C30 C35 1.394(3) . ?
C31 H31 0.9500 . ?
C31 C32 1.387(3) . ?
C32 H32 0.9500 . ?
C32 C33 1.385(3) . ?
C33 H33 0.9500 . ?
C33 C34 1.382(3) . ?
C34 H34 0.9500 . ?
C34 C35 1.387(3) . ?
C35 H35 0.9500 . ?

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
C12 N1 C2 116.90(17) . . ?
C19 N1 C2 111.25(15) . . ?
C19 N1 C12 107.96(16) . . ?
H2 C2 N1 108.25(11) . . ?
C3 C2 N1 103.77(16) . . ?
C3 C2 H2 108.25(11) . . ?
C21 C2 N1 113.56(18) . . ?
C21 C2 H2 108.25(12) . . ?
C21 C2 C3 114.48(17) . . ?
N4 C3 C2 114.48(17) . . ?
C11 C3 C2 109.30(17) . . ?
C11 C3 N4 103.58(15) . . ?
C20 C3 C2 101.19(15) . . ?
C20 C3 N4 116.04(17) . . ?
C20 C3 C11 112.43(17) . . ?
H4 N4 C3 120.8 . . ?
C5 N4 C3 109.55(16) . . ?
C5 N4 H4 118.71(11) . . ?
C6 C5 N4 127.01(19) . . ?
C10 C5 N4 112.09(18) . . ?
C10 C5 C6 120.88(19) . . ?
H6 C6 C5 121.29(12) . . ?
C7 C6 C5 117.4(2) . . ?
C7 C6 H6 121.29(13) . . ?
H7 C7 C6 118.91(13) . . ?
C8 C7 C6 122.2(2) . . ?
C8 C7 H7 118.91(13) . . ?
H8 C8 C7 119.82(13) . . ?
C9 C8 C7 120.4(2) . . ?
C9 C8 H8 119.82(13) . . ?
H9 C9 C8 120.82(13) . . ?
C10 C9 C8 118.4(2) . . ?
C10 C9 H9 120.82(13) . . ?
C9 C10 C5 120.79(19) . . ?
C11 C10 C5 107.55(18) . . ?
C11 C10 C9 131.7(2) . . ?
C10 C11 C3 106.32(17) . . ?
O27 C11 C3 122.85(19) . . ?
O27 C11 C10 130.8(2) . . ?
C13 C12 N1 126.2(2) . . ?
C17 C12 N1 112.86(18) . . ?
C17 C12 C13 120.96(19) . . ?
H13 C13 C12 121.26(13) . . ?
C14 C13 C12 117.5(2) . . ?
C14 C13 H13 121.26(13) . . ?
H14 C14 C13 119.09(13) . . ?
C15 C14 C13 121.8(2) . . ?
C15 C14 H14 119.09(13) . . ?
H15 C15 C14 119.72(13) . . ?
C16 C15 C14 120.6(2) . . ?
C16 C15 H15 119.72(14) . . ?
H16 C16 C15 120.81(14) . . ?
C17 C16 C15 118.4(2) . . ?
C17 C16 H16 120.81(13) . . ?
C16 C17 C12 120.8(2) . . ?
C18 C17 C12 107.89(18) . . ?
C18 C17 C16 131.3(2) . . ?
C19 C18 C17 106.48(18) . . ?
O28 C18 C17 131.07(19) . . ?
O28 C18 C19 122.44(19) . . ?
C18 C19 N1 103.81(16) . . ?
C20 C19 N1 102.55(16) . . ?
C20 C19 C18 114.31(17) . . ?
O29 C19 N1 112.29(17) . . ?
O29 C19 C18 113.04(17) . . ?
O29 C19 C20 110.22(16) . . ?
C19 C20 C3 102.08(16) . . ?
H20 C20 C3 106.02(11) . . ?
H20 C20 C19 106.02(11) . . ?
C30 C20 C3 117.93(16) . . ?
C30 C20 C19 117.72(17) . . ?
C30 C20 H20 106.02(11) . . ?
C22 C21 C2 121.6(2) . . ?
C26 C21 C2 119.4(2) . . ?
C26 C21 C22 119.0(2) . . ?
H22 C22 C21 119.92(14) . . ?
C23 C22 C21 120.2(2) . . ?
C23 C22 H22 119.92(16) . . ?
H23 C23 C22 119.56(16) . . ?
C24 C23 C22 120.9(3) . . ?
C24 C23 H23 119.56(16) . . ?
H24 C24 C23 120.29(16) . . ?
C25 C24 C23 119.4(2) . . ?
C25 C24 H24 120.29(15) . . ?
H25 C25 C24 119.86(15) . . ?
C26 C25 C24 120.3(2) . . ?
C26 C25 H25 119.86(16) . . ?
C25 C26 C21 120.3(2) . . ?
H26 C26 C21 119.86(14) . . ?
H26 C26 C25 119.86(16) . . ?
H29 O29 C19 107.3 . . ?
C31 C30 C20 122.75(19) . . ?
C35 C30 C20 118.86(19) . . ?
C35 C30 C31 118.38(19) . . ?
H31 C31 C30 119.91(12) . . ?
C32 C31 C30 120.2(2) . . ?
C32 C31 H31 119.91(13) . . ?
H32 C32 C31 119.75(13) . . ?
C33 C32 C31 120.5(2) . . ?
C33 C32 H32 119.75(13) . . ?
H33 C33 C32 120.02(13) . . ?
C34 C33 C32 120.0(2) . . ?
C34 C33 H33 120.02(13) . . ?
H34 C34 C33 120.11(13) . . ?
C35 C34 C33 119.8(2) . . ?
C35 C34 H34 120.11(14) . . ?
C34 C35 C30 121.2(2) . . ?
H35 C35 C30 119.42(13) . . ?
H35 C35 C34 119.42(14) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
