# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_200710a
_database_code_depnum_ccdc_archive 'CCDC 2123850'
loop_
_audit_author_name
_audit_author_address
'Jiyuan Du'
;Liaocheng University
China
;
_audit_update_record             
;
2021-11-23 deposited with the CCDC.	2022-05-02 downloaded from the CCDC.
;
_audit_creation_date             2021-11-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H27 N O4 S'
_chemical_formula_sum            'C32 H27 N O4 S'
_chemical_formula_weight         521.60
_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 0.0033 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'
S S 0.1246 0.1234 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.0968(11)
_cell_length_b                   13.8829(15)
_cell_length_c                   16.8118(16)
_cell_angle_alpha                90
_cell_angle_beta                 101.868(3)
_cell_angle_gamma                90
_cell_volume                     2534.6(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3812
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.70
_cell_measurement_theta_min      2.458
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.951
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   0.975
_exptl_transmission_factor_min   0.955
_diffrn_reflns_av_R_equivalents  0.1050
_diffrn_reflns_av_unetI/netI     0.0693
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12496
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.019
_diffrn_reflns_theta_min         1.919
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2889
_reflns_number_total             4458
_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       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4458
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0963
_refine_ls_R_factor_gt           0.0673
_refine_ls_restrained_S_all      0.961
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1133P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1670
_refine_ls_wR_factor_ref         0.1865
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C7(H7)
1.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C12(H12A,H12B)
1.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C11(H11), N1(H1A), C21(H21), C18(H18), C19(H19), C1(H1), C27(H27),
 C24(H24), C17(H17), C23(H23), C5(H5), C3(H3), C4(H4), C28(H28), C30(H30),
 C22(H22), C2(H2), C31(H31)
1.d Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C)
;
_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
S1 S 0.85644(7) 0.72385(6) 0.11078(6) 0.0697(3) Uani 1 1 d . . . . .
O2 O 0.76447(16) 0.64284(13) 0.07051(12) 0.0613(5) Uani 1 1 d . . . . .
C8 C 0.5735(2) 0.53288(17) 0.11252(16) 0.0481(6) Uani 1 1 d . . . . .
O4 O 0.9610(2) 0.72311(19) 0.07519(16) 0.0950(8) Uani 1 1 d . . . . .
O1 O 0.4333(2) 0.40326(14) 0.12182(15) 0.0805(7) Uani 1 1 d . . . . .
C14 C 0.4211(2) 0.58783(17) 0.25613(16) 0.0472(6) Uani 1 1 d . . . . .
C6 C 0.3788(2) 0.73767(19) 0.12474(16) 0.0497(6) Uani 1 1 d . . . . .
C16 C 0.5542(3) 0.5364(2) 0.37966(19) 0.0619(8) Uani 1 1 d . . . . .
H16 H 0.6162 0.4965 0.4073 0.074 Uiso 1 1 calc R U . . .
C11 C 0.5207(2) 0.61349(18) 0.08183(16) 0.0507(6) Uani 1 1 d . . . . .
H11 H 0.5564 0.6541 0.0492 0.061 Uiso 1 1 calc R U . . .
C10 C 0.3898(2) 0.55824(17) 0.16867(17) 0.0487(6) Uani 1 1 d . . . . .
N1 N 0.5511(2) 0.46446(17) 0.24490(16) 0.0684(7) Uani 1 1 d . . . . .
H1A H 0.6025 0.4182 0.2596 0.082 Uiso 1 1 calc R U . . .
C21 C 0.7135(3) 0.39306(19) 0.11660(19) 0.0628(8) Uani 1 1 d . . . . .
H21 H 0.6523 0.3543 0.1300 0.075 Uiso 1 1 calc R U . . .
C9 C 0.4929(2) 0.48545(17) 0.16289(18) 0.0533(7) Uani 1 1 d . . . . .
C15 C 0.5133(2) 0.52908(18) 0.29742(18) 0.0519(7) Uani 1 1 d . . . . .
C18 C 0.4099(3) 0.6639(2) 0.38107(19) 0.0630(8) Uani 1 1 d . . . . .
H18 H 0.3752 0.7097 0.4099 0.076 Uiso 1 1 calc R U . . .
C26 C 0.8981(2) 0.68888(19) 0.21120(19) 0.0574(7) Uani 1 1 d . . . . .
C20 C 0.6907(2) 0.49057(18) 0.10365(16) 0.0508(6) Uani 1 1 d . . . . .
C7 C 0.3996(2) 0.63499(18) 0.10321(17) 0.0491(6) Uani 1 1 d . . . . .
H7 H 0.3361 0.6194 0.0552 0.059 Uiso 1 1 calc R U . . .
C25 C 0.7865(2) 0.54386(19) 0.08467(18) 0.0555(7) Uani 1 1 d . . . . .
C19 C 0.3696(2) 0.65575(19) 0.29854(18) 0.0553(7) Uani 1 1 d . . . . .
H19 H 0.3076 0.6960 0.2714 0.066 Uiso 1 1 calc R U . . .
C1 C 0.4727(3) 0.7964(2) 0.16249(19) 0.0623(8) Uani 1 1 d . . . . .
H1 H 0.5527 0.7727 0.1756 0.075 Uiso 1 1 calc R U . . .
C27 C 0.8099(3) 0.6647(2) 0.2551(2) 0.0687(8) Uani 1 1 d . . . . .
H27 H 0.7271 0.6637 0.2298 0.082 Uiso 1 1 calc R U . . .
C24 C 0.8963(3) 0.5034(3) 0.0780(2) 0.0703(9) Uani 1 1 d . . . . .
H24 H 0.9584 0.5413 0.0648 0.084 Uiso 1 1 calc R U . . .
O3 O 0.7818(2) 0.80682(15) 0.10341(18) 0.0946(8) Uani 1 1 d . . . . .
C17 C 0.5000(3) 0.6055(2) 0.42046(19) 0.0668(8) Uani 1 1 d . . . . .
H17 H 0.5263 0.6118 0.4764 0.080 Uiso 1 1 calc R U . . .
C29 C 0.9657(3) 0.6462(2) 0.3742(2) 0.0709(9) Uani 1 1 d . . . . .
C23 C 0.9140(3) 0.4079(3) 0.0908(2) 0.0792(10) Uani 1 1 d . . . . .
H23 H 0.9885 0.3801 0.0862 0.095 Uiso 1 1 calc R U . . .
C5 C 0.2625(3) 0.7756(2) 0.10600(19) 0.0666(8) Uani 1 1 d . . . . .
H5 H 0.1979 0.7375 0.0791 0.080 Uiso 1 1 calc R U . . .
C13 C 0.3180(3) 0.3975(2) 0.1447(3) 0.0864(11) Uani 1 1 d . . . . .
H13A H 0.3269 0.3672 0.1975 0.104 Uiso 1 1 calc R U . . .
H13B H 0.2609 0.3597 0.1054 0.104 Uiso 1 1 calc R U . . .
C12 C 0.2725(3) 0.4972(2) 0.1475(2) 0.0681(8) Uani 1 1 d . . . . .
H12A H 0.2235 0.5038 0.1887 0.082 Uiso 1 1 calc R U . . .
H12B H 0.2231 0.5161 0.0953 0.082 Uiso 1 1 calc R U . . .
C3 C 0.3331(4) 0.9252(3) 0.1625(2) 0.0877(11) Uani 1 1 d . . . . .
H3 H 0.3177 0.9887 0.1751 0.105 Uiso 1 1 calc R U . . .
C4 C 0.2392(4) 0.8682(3) 0.1259(2) 0.0851(10) Uani 1 1 d . . . . .
H4 H 0.1592 0.8919 0.1142 0.102 Uiso 1 1 calc R U . . .
C28 C 0.8441(3) 0.6425(2) 0.3347(2) 0.0736(9) Uani 1 1 d . . . . .
H28 H 0.7845 0.6245 0.3634 0.088 Uiso 1 1 calc R U . . .
C30 C 1.0504(3) 0.6691(2) 0.3286(2) 0.0790(10) Uani 1 1 d . . . . .
H30 H 1.1332 0.6707 0.3539 0.095 Uiso 1 1 calc R U . . .
C22 C 0.8233(3) 0.3521(2) 0.1103(2) 0.0760(9) Uani 1 1 d . . . . .
H22 H 0.8360 0.2865 0.1193 0.091 Uiso 1 1 calc R U . . .
C2 C 0.4495(4) 0.8901(2) 0.1810(2) 0.0781(10) Uani 1 1 d . . . . .
H2 H 0.5139 0.9296 0.2063 0.094 Uiso 1 1 calc R U . . .
C31 C 1.0189(3) 0.6897(2) 0.2482(2) 0.0697(8) Uani 1 1 d . . . . .
H31 H 1.0791 0.7041 0.2188 0.084 Uiso 1 1 calc R U . . .
C32 C 1.0024(5) 0.6255(3) 0.4616(3) 0.1132(14) Uani 1 1 d . . . . .
H32A H 1.0695 0.5804 0.4708 0.170 Uiso 1 1 calc R U . . .
H32B H 0.9339 0.5986 0.4807 0.170 Uiso 1 1 calc R U . . .
H32C H 1.0280 0.6841 0.4905 0.170 Uiso 1 1 calc R U . . .


_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
S1 O2 1.575(2) . ?
S1 O4 1.411(2) . ?
S1 C26 1.726(3) . ?
S1 O3 1.410(2) . ?
O2 C25 1.407(3) . ?
C8 C11 1.318(3) . ?
C8 C9 1.504(3) . ?
C8 C20 1.463(3) . ?
O1 C9 1.424(3) . ?
O1 C13 1.412(4) . ?
C14 C10 1.497(4) . ?
C14 C15 1.379(4) . ?
C14 C19 1.375(3) . ?
C6 C7 1.500(4) . ?
C6 C1 1.372(4) . ?
C6 C5 1.369(4) . ?
C16 C15 1.368(4) . ?
C16 C17 1.386(4) . ?
C11 C7 1.491(3) . ?
C10 C9 1.544(3) . ?
C10 C7 1.551(4) . ?
C10 C12 1.532(3) . ?
N1 C9 1.427(4) . ?
N1 C15 1.383(3) . ?
C21 C20 1.386(4) . ?
C21 C22 1.368(4) . ?
C18 C19 1.372(4) . ?
C18 C17 1.350(4) . ?
C26 C27 1.383(4) . ?
C26 C31 1.357(4) . ?
C20 C25 1.385(4) . ?
C25 C24 1.367(4) . ?
C1 C2 1.374(4) . ?
C27 C28 1.348(5) . ?
C24 C23 1.350(5) . ?
C29 C28 1.377(5) . ?
C29 C30 1.367(5) . ?
C29 C32 1.471(5) . ?
C23 C22 1.363(5) . ?
C5 C4 1.366(4) . ?
C13 C12 1.479(4) . ?
C3 C4 1.352(5) . ?
C3 C2 1.356(5) . ?
C30 C31 1.355(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
O2 S1 C26 103.84(12) . . ?
O4 S1 O2 109.23(14) . . ?
O4 S1 C26 109.53(14) . . ?
O3 S1 O2 103.21(13) . . ?
O3 S1 O4 119.26(16) . . ?
O3 S1 C26 110.51(16) . . ?
C25 O2 S1 123.34(17) . . ?
C11 C8 C9 108.9(2) . . ?
C11 C8 C20 129.4(2) . . ?
C20 C8 C9 121.7(2) . . ?
C13 O1 C9 105.7(2) . . ?
C15 C14 C10 109.3(2) . . ?
C19 C14 C10 131.3(2) . . ?
C19 C14 C15 119.3(3) . . ?
C1 C6 C7 122.5(2) . . ?
C5 C6 C7 119.6(3) . . ?
C5 C6 C1 117.9(3) . . ?
C15 C16 C17 117.7(3) . . ?
C8 C11 C7 115.2(2) . . ?
C14 C10 C9 102.5(2) . . ?
C14 C10 C7 118.2(2) . . ?
C14 C10 C12 113.2(2) . . ?
C9 C10 C7 104.14(19) . . ?
C12 C10 C9 103.2(2) . . ?
C12 C10 C7 113.2(2) . . ?
C15 N1 C9 110.3(2) . . ?
C22 C21 C20 122.0(3) . . ?
C8 C9 C10 106.4(2) . . ?
O1 C9 C8 110.4(2) . . ?
O1 C9 C10 106.2(2) . . ?
O1 C9 N1 112.2(2) . . ?
N1 C9 C8 115.4(2) . . ?
N1 C9 C10 105.5(2) . . ?
C14 C15 N1 110.7(3) . . ?
C16 C15 C14 121.5(3) . . ?
C16 C15 N1 127.8(3) . . ?
C17 C18 C19 120.1(3) . . ?
C27 C26 S1 120.9(2) . . ?
C31 C26 S1 119.1(2) . . ?
C31 C26 C27 119.9(3) . . ?
C21 C20 C8 120.9(2) . . ?
C25 C20 C8 123.3(2) . . ?
C25 C20 C21 115.7(2) . . ?
C6 C7 C10 116.4(2) . . ?
C11 C7 C6 116.1(2) . . ?
C11 C7 C10 103.4(2) . . ?
C20 C25 O2 116.4(2) . . ?
C24 C25 O2 121.0(3) . . ?
C24 C25 C20 122.6(3) . . ?
C18 C19 C14 119.8(3) . . ?
C6 C1 C2 120.5(3) . . ?
C28 C27 C26 120.0(3) . . ?
C23 C24 C25 119.6(3) . . ?
C18 C17 C16 121.7(3) . . ?
C28 C29 C32 121.2(3) . . ?
C30 C29 C28 117.2(3) . . ?
C30 C29 C32 121.6(4) . . ?
C24 C23 C22 120.4(3) . . ?
C4 C5 C6 121.5(3) . . ?
O1 C13 C12 106.9(2) . . ?
C13 C12 C10 104.2(2) . . ?
C4 C3 C2 120.2(3) . . ?
C3 C4 C5 119.8(3) . . ?
C27 C28 C29 121.2(3) . . ?
C31 C30 C29 122.8(3) . . ?
C23 C22 C21 119.8(3) . . ?
C3 C2 C1 120.1(3) . . ?
C30 C31 C26 118.9(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_210527b
_database_code_depnum_ccdc_archive 'CCDC 2123851'
loop_
_audit_author_name
_audit_author_address
'Jiyuan Du'
;Liaocheng University
China
;
_audit_update_record             
;
2021-11-23 deposited with the CCDC.	2022-05-02 downloaded from the CCDC.
;
_audit_creation_date             2021-11-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H23 N O2'
_chemical_formula_sum            'C25 H23 N O2'
_chemical_formula_weight         369.44
_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      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   19.8233(16)
_cell_length_b                   10.5498(9)
_cell_length_c                   18.1025(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3785.8(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1830
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.5640
_cell_measurement_theta_min      4.4490
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.910
_exptl_absorpt_coefficient_mu    0.643
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_correction_T_min  0.908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            coloueless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_unetI/netI     0.0623
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8128
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.046
_diffrn_reflns_theta_min         4.461
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1992
_reflns_number_total             3313
_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       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.00143(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3313
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1010
_refine_ls_R_factor_gt           0.0558
_refine_ls_restrained_S_all      0.992
_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)+(0.0807P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1414
_refine_ls_wR_factor_ref         0.1669
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C17(H17), C19(H19)
1.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C10(H10A,H10B), C18(H18A,H18B)
1.c Aromatic/amide H refined with riding coordinates:
 N1(H1A), C1(H1), C2(H2A), C3(H3), C4(H4), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C21(H21), C22(H22), C23(H23), C24(H24)
1.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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
O1 O 0.45038(10) 0.17118(19) 0.16750(12) 0.0591(6) Uani 1 1 d . . . . .
O2 O 0.55148(11) 0.0001(2) 0.17071(14) 0.0742(7) Uani 1 1 d . . . . .
H2 H 0.5234 0.0571 0.1684 0.111 Uiso 1 1 calc R U . . .
N1 N 0.36798(11) 0.0100(2) 0.18548(12) 0.0486(6) Uani 1 1 d . . . . .
H1A H 0.3859 -0.0535 0.2079 0.058 Uiso 1 1 calc R U . . .
C1 C 0.25500(15) 0.0064(3) 0.24590(16) 0.0530(8) Uani 1 1 d . . . . .
H1 H 0.2661 -0.0569 0.2795 0.064 Uiso 1 1 calc R U . . .
C2 C 0.19121(16) 0.0602(3) 0.24461(18) 0.0627(9) Uani 1 1 d . . . . .
H2A H 0.1589 0.0321 0.2780 0.075 Uiso 1 1 calc R U . . .
C3 C 0.17448(17) 0.1547(3) 0.19475(17) 0.0648(9) Uani 1 1 d . . . . .
H3 H 0.1314 0.1895 0.1950 0.078 Uiso 1 1 calc R U . . .
C4 C 0.22206(16) 0.1972(3) 0.14463(17) 0.0592(9) Uani 1 1 d . . . . .
H4 H 0.2112 0.2614 0.1115 0.071 Uiso 1 1 calc R U . . .
C5 C 0.28553(14) 0.1443(2) 0.14394(14) 0.0449(7) Uani 1 1 d . . . . .
C6 C 0.30159(14) 0.0511(2) 0.19489(14) 0.0437(7) Uani 1 1 d . . . . .
C7 C 0.37340(17) 0.3101(3) 0.11173(17) 0.0595(9) Uani 1 1 d . . . . .
H7A H 0.3977 0.3421 0.0691 0.071 Uiso 1 1 calc R U . . .
H7B H 0.3368 0.3677 0.1235 0.071 Uiso 1 1 calc R U . . .
C8 C 0.34686(14) 0.1751(2) 0.09772(14) 0.0435(7) Uani 1 1 d . . . . .
C9 C 0.40208(14) 0.0892(3) 0.13279(14) 0.0450(7) Uani 1 1 d . . . . .
C10 C 0.4198(2) 0.2932(3) 0.1766(3) 0.0920(13) Uani 1 1 d . . . . .
H10A H 0.4538 0.3591 0.1773 0.110 Uiso 1 1 calc R U . . .
H10B H 0.3946 0.2967 0.2225 0.110 Uiso 1 1 calc R U . . .
C11 C 0.22570(15) 0.0580(3) -0.01223(16) 0.0542(8) Uani 1 1 d . . . . .
H11 H 0.2322 -0.0083 0.0208 0.065 Uiso 1 1 calc R U . . .
C12 C 0.16428(16) 0.0696(3) -0.04787(17) 0.0604(8) Uani 1 1 d . . . . .
H12 H 0.1301 0.0112 -0.0388 0.072 Uiso 1 1 calc R U . . .
C13 C 0.15366(18) 0.1674(3) -0.09663(18) 0.0647(9) Uani 1 1 d . . . . .
H13 H 0.1122 0.1762 -0.1202 0.078 Uiso 1 1 calc R U . . .
C14 C 0.20457(18) 0.2517(3) -0.11014(18) 0.0672(9) Uani 1 1 d . . . . .
H14 H 0.1978 0.3179 -0.1433 0.081 Uiso 1 1 calc R U . . .
C15 C 0.26619(16) 0.2392(3) -0.07472(15) 0.0532(8) Uani 1 1 d . . . . .
H15 H 0.3004 0.2969 -0.0849 0.064 Uiso 1 1 calc R U . . .
C16 C 0.27784(14) 0.1429(2) -0.02461(14) 0.0429(6) Uani 1 1 d . . . . .
C17 C 0.34486(14) 0.1331(2) 0.01452(14) 0.0445(7) Uani 1 1 d . . . . .
H17 H 0.3764 0.1881 -0.0122 0.053 Uiso 1 1 calc R U . . .
C18 C 0.37630(13) 0.0004(2) 0.01588(15) 0.0459(7) Uani 1 1 d . . . . .
H18A H 0.3439 -0.0621 0.0329 0.055 Uiso 1 1 calc R U . . .
H18B H 0.3922 -0.0237 -0.0328 0.055 Uiso 1 1 calc R U . . .
C19 C 0.43524(14) 0.0124(2) 0.07014(15) 0.0435(7) Uani 1 1 d . . . . .
H19 H 0.4692 0.0670 0.0470 0.052 Uiso 1 1 calc R U . . .
C20 C 0.47001(14) -0.1087(3) 0.09228(15) 0.0452(7) Uani 1 1 d . . . . .
C21 C 0.45047(15) -0.2250(3) 0.06434(18) 0.0580(8) Uani 1 1 d . . . . .
H21 H 0.4142 -0.2279 0.0318 0.070 Uiso 1 1 calc R U . . .
C22 C 0.48249(18) -0.3376(3) 0.0827(2) 0.0717(10) Uani 1 1 d . . . . .
H22 H 0.4683 -0.4140 0.0624 0.086 Uiso 1 1 calc R U . . .
C23 C 0.53562(19) -0.3342(4) 0.1314(2) 0.0773(11) Uani 1 1 d . . . . .
H23 H 0.5571 -0.4090 0.1450 0.093 Uiso 1 1 calc R U . . .
C24 C 0.55718(18) -0.2203(4) 0.16004(19) 0.0722(10) Uani 1 1 d . . . . .
H24 H 0.5937 -0.2183 0.1923 0.087 Uiso 1 1 calc R U . . .
C25 C 0.52485(16) -0.1089(3) 0.14113(16) 0.0577(8) 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 C9 1.435(3) . ?
O1 C10 1.433(4) . ?
O2 C25 1.374(4) . ?
N1 C6 1.396(3) . ?
N1 C9 1.437(3) . ?
C1 C2 1.386(4) . ?
C1 C6 1.389(4) . ?
C2 C3 1.386(4) . ?
C3 C4 1.383(4) . ?
C4 C5 1.377(4) . ?
C5 C6 1.385(4) . ?
C5 C8 1.511(4) . ?
C7 C8 1.539(3) . ?
C7 C10 1.502(5) . ?
C8 C9 1.556(4) . ?
C8 C17 1.570(4) . ?
C9 C19 1.541(4) . ?
C11 C12 1.383(4) . ?
C11 C16 1.386(4) . ?
C12 C13 1.374(4) . ?
C13 C14 1.367(4) . ?
C14 C15 1.386(4) . ?
C15 C16 1.381(4) . ?
C16 C17 1.509(4) . ?
C17 C18 1.532(3) . ?
C18 C19 1.532(4) . ?
C19 C20 1.506(4) . ?
C20 C21 1.383(4) . ?
C20 C25 1.401(4) . ?
C21 C22 1.386(4) . ?
C22 C23 1.374(5) . ?
C23 C24 1.377(5) . ?
C24 C25 1.382(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
C10 O1 C9 108.0(2) . . ?
C6 N1 C9 110.1(2) . . ?
C2 C1 C6 117.2(3) . . ?
C3 C2 C1 121.6(3) . . ?
C4 C3 C2 119.8(3) . . ?
C5 C4 C3 119.8(3) . . ?
C4 C5 C6 119.5(3) . . ?
C4 C5 C8 130.8(3) . . ?
C6 C5 C8 109.7(2) . . ?
C1 C6 N1 127.0(2) . . ?
C5 C6 N1 110.9(2) . . ?
C5 C6 C1 122.1(3) . . ?
C10 C7 C8 103.2(2) . . ?
C5 C8 C7 112.5(2) . . ?
C5 C8 C9 102.4(2) . . ?
C5 C8 C17 116.7(2) . . ?
C7 C8 C9 103.4(2) . . ?
C7 C8 C17 115.3(2) . . ?
C9 C8 C17 104.2(2) . . ?
O1 C9 N1 111.9(2) . . ?
O1 C9 C8 107.3(2) . . ?
O1 C9 C19 110.8(2) . . ?
N1 C9 C8 106.2(2) . . ?
N1 C9 C19 112.5(2) . . ?
C19 C9 C8 107.8(2) . . ?
O1 C10 C7 106.0(3) . . ?
C12 C11 C16 121.6(3) . . ?
C13 C12 C11 120.1(3) . . ?
C14 C13 C12 119.4(3) . . ?
C13 C14 C15 120.4(3) . . ?
C16 C15 C14 121.4(3) . . ?
C11 C16 C17 122.4(2) . . ?
C15 C16 C11 117.2(3) . . ?
C15 C16 C17 120.4(3) . . ?
C16 C17 C8 116.9(2) . . ?
C16 C17 C18 115.3(2) . . ?
C18 C17 C8 103.4(2) . . ?
C19 C18 C17 104.2(2) . . ?
C18 C19 C9 101.0(2) . . ?
C20 C19 C9 116.5(2) . . ?
C20 C19 C18 116.7(2) . . ?
C21 C20 C19 121.8(3) . . ?
C21 C20 C25 116.6(3) . . ?
C25 C20 C19 121.6(3) . . ?
C20 C21 C22 123.0(3) . . ?
C23 C22 C21 118.8(3) . . ?
C22 C23 C24 120.1(3) . . ?
C23 C24 C25 120.3(3) . . ?
O2 C25 C20 122.9(3) . . ?
O2 C25 C24 115.9(3) . . ?
C24 C25 C20 121.1(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
