# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_rs144
_database_code_depnum_ccdc_archive 'CCDC 2120133'
loop_
_audit_author_name
_audit_author_address
'Roger D. Sommer'
;NC State University
United States of America
;
_audit_update_record             
;
2021-11-03 deposited with the CCDC.	2022-01-17 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            VP-17
_chemical_formula_moiety         'C36 H34 N4'
_chemical_formula_sum            'C36 H34 N4'
_chemical_formula_iupac          ?
_chemical_formula_weight         522.67

_chemical_melting_point          ?

_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                   6.95760(10)
_cell_length_b                   8.7932(2)
_cell_length_c                   12.4732(2)
_cell_angle_alpha                106.0936(6)
_cell_angle_beta                 105.0837(6)
_cell_angle_gamma                98.5367(6)
_cell_volume                     687.64(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9920
_cell_measurement_theta_min      5.3905
_cell_measurement_theta_max      72.1029
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            'dark red'
_exptl_crystal_size_max          0.353
_exptl_crystal_size_mid          0.097
_exptl_crystal_size_min          0.044
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             278

_exptl_absorpt_coefficient_mu    0.575
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_source_power             0.06
_diffrn_source_current           1.1
_diffrn_source_voltage           50

_diffrn_radiation_probe          ?
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'multilayer mirror'

_diffrn_measurement_device       'κ--geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            18219
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_theta_min         3.89
_diffrn_reflns_theta_max         72.10
_diffrn_reflns_theta_full        67.68
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15

_refine_special_details          
;
H1 is located from difference map. position is allowed to refine freely, while
isotrpoic displacement parameter set to 1.2x parent atom (N1).
;

_reflns_number_total             2709
_reflns_number_gt                2619
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0349
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0865
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_number_reflns         2709
_refine_ls_number_parameters     186
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0382P)²+0.2881P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.225
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       
'Bruker Instrument Service, BIS, v.6.2.10 (Bruker AXS Inc., 2018)'
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'XS, VERSION 2013/1'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, 2019)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 1.15101(13) 0.31534(11) 0.49819(7) 0.01647(19) Uani d . . . 1 . .
H H1 1.099(2) 0.4034(17) 0.5075(11) 0.02 Uiso d U . . 1 . .
N N2 0.72819(13) 0.35536(10) 0.35953(7) 0.01665(19) Uani d . . . 1 . .
C C1 1.33995(15) 0.31599(13) 0.56893(9) 0.0171(2) Uani d . . . 1 . .
C C2 1.36589(17) 0.15481(13) 0.53086(9) 0.0212(2) Uani d . . . 1 . .
H H2 1.482619 0.118108 0.562701 0.025 Uiso calc U . R 1 . .
C C3 1.19367(17) 0.06129(13) 0.44034(10) 0.0227(2) Uani d . . . 1 . .
H H3 1.170734 -0.051337 0.398375 0.027 Uiso calc U . R 1 . .
C C4 1.05538(16) 0.16135(13) 0.41993(9) 0.0187(2) Uani d . . . 1 . .
C C5 0.85933(16) 0.10898(13) 0.33811(9) 0.0196(2) Uani d . . . 1 . .
H H5 0.820537 -0.003826 0.29355 0.023 Uiso calc U . R 1 . .
C C6 0.71161(16) 0.19419(12) 0.31100(9) 0.0180(2) Uani d . . . 1 . .
C C7 0.50373(16) 0.11061(13) 0.22142(9) 0.0215(2) Uani d . . . 1 . .
H H7A 0.411905 0.056646 0.255658 0.026 Uiso calc U . R 1 . .
H H7B 0.514511 0.02872 0.15188 0.026 Uiso calc U . R 1 . .
C C8 0.42716(16) 0.25160(13) 0.18905(9) 0.0188(2) Uani d . . . 1 . .
C C9 0.55849(15) 0.39470(12) 0.30099(9) 0.0161(2) Uani d . . . 1 . .
C C10 0.52496(15) 0.55126(13) 0.33534(9) 0.0165(2) Uani d . . . 1 . .
C C11 0.19355(16) 0.22003(14) 0.15635(10) 0.0244(2) Uani d . . . 1 . .
H H11A 0.131155 0.112471 0.096272 0.037 Uiso calc U . R 1 . .
H H11B 0.146975 0.303846 0.125426 0.037 Uiso calc U . R 1 . .
H H11C 0.152978 0.223574 0.226417 0.037 Uiso calc U . R 1 . .
C C12 0.49618(18) 0.27436(14) 0.08562(9) 0.0242(2) Uani d . . . 1 . .
H H12A 0.644585 0.285762 0.105108 0.036 Uiso calc U . R 1 . .
H H12B 0.462142 0.372515 0.070932 0.036 Uiso calc U . R 1 . .
H H12C 0.425729 0.179277 0.015006 0.036 Uiso calc U . R 1 . .
C C13 0.33945(15) 0.59332(12) 0.26845(9) 0.0168(2) Uani d . . . 1 . .
C C14 0.16189(16) 0.58158(13) 0.30091(9) 0.0210(2) Uani d . . . 1 . .
H H14 0.157507 0.544648 0.36515 0.025 Uiso calc U . R 1 . .
C C15 -0.00854(16) 0.62333(13) 0.24028(10) 0.0221(2) Uani d . . . 1 . .
H H15 -0.129041 0.613794 0.262712 0.027 Uiso calc U . R 1 . .
C C16 -0.00329(16) 0.67884(13) 0.14720(9) 0.0216(2) Uani d . . . 1 . .
H H16 -0.120343 0.706437 0.105329 0.026 Uiso calc U . R 1 . .
C C17 0.17363(17) 0.69398(14) 0.11534(9) 0.0223(2) Uani d . . . 1 . .
H H17 0.178165 0.733038 0.052036 0.027 Uiso calc U . R 1 . .
C C18 0.34379(16) 0.65219(13) 0.17576(9) 0.0195(2) Uani d . . . 1 . .
H H18 0.464721 0.663733 0.153861 0.023 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C4 . 1.3750(13) ?
N1 C1 . 1.3777(13) ?
N1 H1 . 0.894(14) ?
N2 C6 . 1.3520(13) ?
N2 C9 . 1.3636(13) ?
C1 C10 2_766 1.4103(15) ?
C1 C2 . 1.4192(14) ?
C2 C3 . 1.3694(16) ?
C2 H2 . 0.95 ?
C3 C4 . 1.4187(15) ?
C3 H3 . 0.95 ?
C4 C5 . 1.3938(15) ?
C5 C6 . 1.3857(15) ?
C5 H5 . 0.95 ?
C6 C7 . 1.5061(14) ?
C7 C8 . 1.5314(14) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C8 C11 . 1.5308(14) ?
C8 C12 . 1.5402(15) ?
C8 C9 . 1.5454(14) ?
C9 C10 . 1.3978(14) ?
C10 C13 . 1.5003(13) ?
C11 H11A . 0.98 ?
C11 H11B . 0.98 ?
C11 H11C . 0.98 ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C13 C14 . 1.3951(14) ?
C13 C18 . 1.3967(14) ?
C14 C15 . 1.3890(15) ?
C14 H14 . 0.95 ?
C15 C16 . 1.3850(16) ?
C15 H15 . 0.95 ?
C16 C17 . 1.3878(16) ?
C16 H16 . 0.95 ?
C17 C18 . 1.3868(15) ?
C17 H17 . 0.95 ?
C18 H18 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 N1 C1 . . 110.37(9) ?
C4 N1 H1 . . 126.8(8) ?
C1 N1 H1 . . 122.7(8) ?
C6 N2 C9 . . 108.70(8) ?
N1 C1 C10 . 2_766 126.49(9) ?
N1 C1 C2 . . 106.49(9) ?
C10 C1 C2 2_766 . 126.92(10) ?
C3 C2 C1 . . 108.24(9) ?
C3 C2 H2 . . 125.9 ?
C1 C2 H2 . . 125.9 ?
C2 C3 C4 . . 108.33(10) ?
C2 C3 H3 . . 125.8 ?
C4 C3 H3 . . 125.8 ?
N1 C4 C5 . . 127.88(9) ?
N1 C4 C3 . . 106.53(9) ?
C5 C4 C3 . . 125.56(10) ?
C6 C5 C4 . . 130.69(10) ?
C6 C5 H5 . . 114.7 ?
C4 C5 H5 . . 114.7 ?
N2 C6 C5 . . 126.76(10) ?
N2 C6 C7 . . 111.44(9) ?
C5 C6 C7 . . 121.79(9) ?
C6 C7 C8 . . 102.86(8) ?
C6 C7 H7A . . 111.2 ?
C8 C7 H7A . . 111.2 ?
C6 C7 H7B . . 111.2 ?
C8 C7 H7B . . 111.2 ?
H7A C7 H7B . . 109.1 ?
C11 C8 C7 . . 111.14(9) ?
C11 C8 C12 . . 110.17(9) ?
C7 C8 C12 . . 109.26(9) ?
C11 C8 C9 . . 118.41(9) ?
C7 C8 C9 . . 99.52(8) ?
C12 C8 C9 . . 107.67(8) ?
N2 C9 C10 . . 122.25(9) ?
N2 C9 C8 . . 111.32(8) ?
C10 C9 C8 . . 126.17(9) ?
C9 C10 C1 . 2_766 124.66(9) ?
C9 C10 C13 . . 121.54(9) ?
C1 C10 C13 2_766 . 113.77(9) ?
C8 C11 H11A . . 109.5 ?
C8 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C8 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C8 C12 H12A . . 109.5 ?
C8 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C8 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C14 C13 C18 . . 118.49(9) ?
C14 C13 C10 . . 120.71(9) ?
C18 C13 C10 . . 120.73(9) ?
C15 C14 C13 . . 120.69(10) ?
C15 C14 H14 . . 119.7 ?
C13 C14 H14 . . 119.7 ?
C16 C15 C14 . . 120.18(10) ?
C16 C15 H15 . . 119.9 ?
C14 C15 H15 . . 119.9 ?
C15 C16 C17 . . 119.75(10) ?
C15 C16 H16 . . 120.1 ?
C17 C16 H16 . . 120.1 ?
C18 C17 C16 . . 120.10(10) ?
C18 C17 H17 . . 119.9 ?
C16 C17 H17 . . 119.9 ?
C17 C18 C13 . . 120.77(10) ?
C17 C18 H18 . . 119.6 ?
C13 C18 H18 . . 119.6 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C4 N1 C1 C10 . . . 2_766 -175.11(10) ?
C4 N1 C1 C2 . . . . 1.52(11) ?
N1 C1 C2 C3 . . . . -0.73(12) ?
C10 C1 C2 C3 2_766 . . . 175.89(10) ?
C1 C2 C3 C4 . . . . -0.30(13) ?
C1 N1 C4 C5 . . . . 176.56(10) ?
C1 N1 C4 C3 . . . . -1.70(11) ?
C2 C3 C4 N1 . . . . 1.21(12) ?
C2 C3 C4 C5 . . . . -177.10(10) ?
N1 C4 C5 C6 . . . . 1.69(19) ?
C3 C4 C5 C6 . . . . 179.63(11) ?
C9 N2 C6 C5 . . . . 173.95(10) ?
C9 N2 C6 C7 . . . . -7.37(11) ?
C4 C5 C6 N2 . . . . 1.10(19) ?
C4 C5 C6 C7 . . . . -177.46(11) ?
N2 C6 C7 C8 . . . . 20.74(11) ?
C5 C6 C7 C8 . . . . -160.50(10) ?
C6 C7 C8 C11 . . . . -148.80(9) ?
C6 C7 C8 C12 . . . . 89.41(10) ?
C6 C7 C8 C9 . . . . -23.21(10) ?
C6 N2 C9 C10 . . . . 176.08(9) ?
C6 N2 C9 C8 . . . . -9.53(11) ?
C11 C8 C9 N2 . . . . 141.76(9) ?
C7 C8 C9 N2 . . . . 21.34(10) ?
C12 C8 C9 N2 . . . . -92.52(10) ?
C11 C8 C9 C10 . . . . -44.12(15) ?
C7 C8 C9 C10 . . . . -164.55(10) ?
C12 C8 C9 C10 . . . . 81.60(12) ?
N2 C9 C10 C1 . . . 2_766 0.80(16) ?
C8 C9 C10 C1 . . . 2_766 -172.72(9) ?
N2 C9 C10 C13 . . . . 178.74(9) ?
C8 C9 C10 C13 . . . . 5.22(15) ?
C9 C10 C13 C14 . . . . 92.71(12) ?
C1 C10 C13 C14 2_766 . . . -89.13(12) ?
C9 C10 C13 C18 . . . . -90.25(13) ?
C1 C10 C13 C18 2_766 . . . 87.91(12) ?
C18 C13 C14 C15 . . . . 1.73(16) ?
C10 C13 C14 C15 . . . . 178.83(10) ?
C13 C14 C15 C16 . . . . -0.63(17) ?
C14 C15 C16 C17 . . . . -0.57(16) ?
C15 C16 C17 C18 . . . . 0.62(16) ?
C16 C17 C18 C13 . . . . 0.52(16) ?
C14 C13 C18 C17 . . . . -1.67(16) ?
C10 C13 C18 C17 . . . . -178.78(10) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 N2 . 0.894(14) 2.647(13) 3.1251(12) 114.4(10) ?
N1 H1 N2 2_766 0.894(14) 2.225(13) 2.8094(12) 122.6(10) ?

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 2120236'
loop_
_audit_author_name
_audit_author_address
'Roger D. Sommer'
;NC State University
United States of America
;
_audit_update_record             
;
2021-11-03 deposited with the CCDC.	2022-01-17 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            TS-16
_chemical_formula_moiety         'C34 H42 N4 O4'
_chemical_formula_sum            'C34 H42 N4 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         570.71

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_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                   6.9814(3)
_cell_length_b                   9.7210(5)
_cell_length_c                   11.6464(5)
_cell_angle_alpha                75.978(3)
_cell_angle_beta                 85.771(2)
_cell_angle_gamma                75.899(3)
_cell_volume                     743.65(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    104
_cell_measurement_theta_min      2.4921
_cell_measurement_theta_max      28.6931
_cell_measurement_temperature    110.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.419
_exptl_crystal_size_mid          0.246
_exptl_crystal_size_min          0.151
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             306

_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_T_max  0.75

_exptl_special_details           
;
;

_diffrn_ambient_temperature      110.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker-Nonius X8 Kappa APEX II'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            20131
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         32.88
_diffrn_reflns_theta_full        32.88
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_reflns_number_total             5461
_reflns_number_gt                4162
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_gt          0.1093
_refine_ls_wR_factor_ref         0.1202
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_number_reflns         5461
_refine_ls_number_parameters     198
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
w=1/[σ²(Fo²)+(0.0612P)²+0.1057P]
where P=(Fo²+2Fc²)/3
;

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.286
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'APEX2 v2012.4-3 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS Inc., 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 -0.09774(11) 0.12458(8) 0.58314(6) 0.02293(16) Uani d . . . 1 . .
O O2 -0.22346(10) 0.21200(8) 0.40080(6) 0.02007(15) Uani d . . . 1 . .
N N1 0.26915(12) 0.42422(9) 0.44620(6) 0.01582(15) Uani d . . . 1 . .
H H1 0.3661(19) 0.4570(14) 0.4710(11) 0.027(3) Uiso d . . . 1 . .
N N2 0.48509(12) 0.36609(8) 0.66702(6) 0.01605(15) Uani d . . . 1 . .
C C1 0.19419(14) 0.46886(10) 0.33393(7) 0.01609(17) Uani d . . . 1 . .
C C2 0.04416(14) 0.39371(10) 0.33060(8) 0.01692(17) Uani d . . . 1 . .
C C3 0.03272(13) 0.30473(10) 0.44314(8) 0.01574(17) Uani d . . . 1 . .
C C4 0.17515(13) 0.32504(10) 0.51598(8) 0.01555(17) Uani d . . . 1 . .
C C5 0.21744(14) 0.25876(10) 0.63466(8) 0.01740(18) Uani d . . . 1 . .
H H5 0.1392 0.1932 0.6734 0.021 Uiso calc U . R 1 . .
C C6 0.35962(15) 0.27706(10) 0.70275(8) 0.01722(18) Uani d . . . 1 . .
C C7 0.38489(17) 0.19688(12) 0.83125(8) 0.0240(2) Uani d . . . 1 . .
H H7A 0.4071 0.0903 0.84 0.029 Uiso calc U . R 1 . .
H H7B 0.2675 0.2303 0.8792 0.029 Uiso calc U . R 1 . .
C C8 0.56740(15) 0.23605(10) 0.86810(8) 0.01836(18) Uani d . . . 1 . .
C C9 0.60173(14) 0.35223(10) 0.75917(7) 0.01641(17) Uani d . . . 1 . .
C C10 0.74485(14) 0.42854(10) 0.75842(8) 0.01762(18) Uani d . . . 1 . .
H H10 0.8114 0.4084 0.831 0.021 Uiso calc U . R 1 . .
C C11 -0.06552(15) 0.40808(12) 0.22068(8) 0.0214(2) Uani d . . . 1 . .
H H11A -0.0614 0.5023 0.1652 0.026 Uiso calc U . R 1 . .
H H11B -0.2056 0.4081 0.2416 0.026 Uiso calc U . R 1 . .
C C12 0.02308(17) 0.28376(17) 0.15960(10) 0.0361(3) Uani d . . . 1 . .
H H12A 0.162 0.283 0.1393 0.054 Uiso calc U . R 1 . .
H H12B -0.0498 0.298 0.0873 0.054 Uiso calc U . R 1 . .
H H12C 0.0138 0.1906 0.213 0.054 Uiso calc U . R 1 . .
C C13 -0.09903(14) 0.20479(10) 0.48545(8) 0.01674(17) Uani d . . . 1 . .
C C14 -0.35566(14) 0.11474(11) 0.42990(8) 0.01901(18) Uani d . . . 1 . .
H H14A -0.4529 0.1425 0.4914 0.023 Uiso calc U . R 1 . .
H H14B -0.2809 0.013 0.4596 0.023 Uiso calc U . R 1 . .
C C15 -0.45812(16) 0.12974(12) 0.31664(9) 0.0237(2) Uani d . . . 1 . .
H H15A -0.5271 0.2317 0.2869 0.036 Uiso calc U . R 1 . .
H H15B -0.5538 0.0682 0.3317 0.036 Uiso calc U . R 1 . .
H H15C -0.3602 0.099 0.2576 0.036 Uiso calc U . R 1 . .
C C16 0.74674(19) 0.10646(13) 0.88404(11) 0.0349(3) Uani d . . . 1 . .
H H16A 0.7731 0.0725 0.8105 0.052 Uiso calc U . R 1 . .
H H16B 0.7198 0.0273 0.9484 0.052 Uiso calc U . R 1 . .
H H16C 0.8622 0.1366 0.9034 0.052 Uiso calc U . R 1 . .
C C17 0.52686(16) 0.29449(13) 0.98023(8) 0.0251(2) Uani d . . . 1 . .
H H17A 0.4132 0.3784 0.9679 0.038 Uiso calc U . R 1 . .
H H17B 0.6432 0.3246 0.9983 0.038 Uiso calc U . R 1 . .
H H17C 0.4982 0.2179 1.0464 0.038 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C13 . 1.2128(11) ?
O2 C13 . 1.3396(11) ?
O2 C14 . 1.4438(12) ?
N1 C4 . 1.3677(12) ?
N1 C1 . 1.3738(11) ?
N1 H1 . 0.907(13) ?
N2 C6 . 1.3530(12) ?
N2 C9 . 1.3559(11) ?
C1 C10 2_666 1.3972(12) ?
C1 C2 . 1.4230(13) ?
C2 C3 . 1.3933(12) ?
C2 C11 . 1.5002(13) ?
C3 C4 . 1.4313(13) ?
C3 C13 . 1.4729(13) ?
C4 C5 . 1.3959(12) ?
C5 C6 . 1.3844(13) ?
C5 H5 . 0.95 ?
C6 C7 . 1.5116(13) ?
C7 C8 . 1.5327(15) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C8 C17 . 1.5281(13) ?
C8 C9 . 1.5282(12) ?
C8 C16 . 1.5301(15) ?
C9 C10 . 1.3804(14) ?
C10 C1 2_666 1.3972(12) ?
C10 H10 . 0.95 ?
C11 C12 . 1.5286(16) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C14 C15 . 1.5059(13) ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?
C15 H15A . 0.98 ?
C15 H15B . 0.98 ?
C15 H15C . 0.98 ?
C16 H16A . 0.98 ?
C16 H16B . 0.98 ?
C16 H16C . 0.98 ?
C17 H17A . 0.98 ?
C17 H17B . 0.98 ?
C17 H17C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C13 O2 C14 . . 116.49(7) ?
C4 N1 C1 . . 110.60(8) ?
C4 N1 H1 . . 124.6(8) ?
C1 N1 H1 . . 124.8(8) ?
C6 N2 C9 . . 108.30(7) ?
N1 C1 C10 . 2_666 125.18(9) ?
N1 C1 C2 . . 107.69(8) ?
C10 C1 C2 2_666 . 127.13(8) ?
C3 C2 C1 . . 106.85(8) ?
C3 C2 C11 . . 129.62(9) ?
C1 C2 C11 . . 123.45(8) ?
C2 C3 C4 . . 108.25(8) ?
C2 C3 C13 . . 128.19(8) ?
C4 C3 C13 . . 123.57(8) ?
N1 C4 C5 . . 124.64(9) ?
N1 C4 C3 . . 106.60(7) ?
C5 C4 C3 . . 128.75(9) ?
C6 C5 C4 . . 127.85(9) ?
C6 C5 H5 . . 116.1 ?
C4 C5 H5 . . 116.1 ?
N2 C6 C5 . . 126.33(8) ?
N2 C6 C7 . . 112.67(8) ?
C5 C6 C7 . . 120.98(9) ?
C6 C7 C8 . . 103.68(8) ?
C6 C7 H7A . . 111.0 ?
C8 C7 H7A . . 111.0 ?
C6 C7 H7B . . 111.0 ?
C8 C7 H7B . . 111.0 ?
H7A C7 H7B . . 109.0 ?
C17 C8 C9 . . 112.55(8) ?
C17 C8 C16 . . 110.63(9) ?
C9 C8 C16 . . 109.05(8) ?
C17 C8 C7 . . 111.53(8) ?
C9 C8 C7 . . 101.14(7) ?
C16 C8 C7 . . 111.61(9) ?
N2 C9 C10 . . 125.64(8) ?
N2 C9 C8 . . 113.45(8) ?
C10 C9 C8 . . 120.87(8) ?
C9 C10 C1 . 2_666 129.21(8) ?
C9 C10 H10 . . 115.4 ?
C1 C10 H10 2_666 . 115.4 ?
C2 C11 C12 . . 111.69(8) ?
C2 C11 H11A . . 109.3 ?
C12 C11 H11A . . 109.3 ?
C2 C11 H11B . . 109.3 ?
C12 C11 H11B . . 109.3 ?
H11A C11 H11B . . 107.9 ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
O1 C13 O2 . . 123.09(9) ?
O1 C13 C3 . . 125.79(9) ?
O2 C13 C3 . . 111.12(8) ?
O2 C14 C15 . . 105.84(8) ?
O2 C14 H14A . . 110.6 ?
C15 C14 H14A . . 110.6 ?
O2 C14 H14B . . 110.6 ?
C15 C14 H14B . . 110.6 ?
H14A C14 H14B . . 108.7 ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C8 C16 H16A . . 109.5 ?
C8 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C8 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C8 C17 H17A . . 109.5 ?
C8 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C8 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C4 N1 C1 C10 . . . 2_666 178.81(9) ?
C4 N1 C1 C2 . . . . -0.38(10) ?
N1 C1 C2 C3 . . . . 0.16(10) ?
C10 C1 C2 C3 2_666 . . . -179.01(9) ?
N1 C1 C2 C11 . . . . -176.80(9) ?
C10 C1 C2 C11 2_666 . . . 4.03(15) ?
C1 C2 C3 C4 . . . . 0.11(10) ?
C11 C2 C3 C4 . . . . 176.81(9) ?
C1 C2 C3 C13 . . . . -179.81(9) ?
C11 C2 C3 C13 . . . . -3.11(16) ?
C1 N1 C4 C5 . . . . 179.89(9) ?
C1 N1 C4 C3 . . . . 0.45(10) ?
C2 C3 C4 N1 . . . . -0.34(10) ?
C13 C3 C4 N1 . . . . 179.59(8) ?
C2 C3 C4 C5 . . . . -179.75(9) ?
C13 C3 C4 C5 . . . . 0.17(15) ?
N1 C4 C5 C6 . . . . -1.19(16) ?
C3 C4 C5 C6 . . . . 178.13(9) ?
C9 N2 C6 C5 . . . . -179.62(9) ?
C9 N2 C6 C7 . . . . 1.78(11) ?
C4 C5 C6 N2 . . . . 1.09(17) ?
C4 C5 C6 C7 . . . . 179.58(10) ?
N2 C6 C7 C8 . . . . -6.75(11) ?
C5 C6 C7 C8 . . . . 174.57(9) ?
C6 C7 C8 C17 . . . . 127.97(9) ?
C6 C7 C8 C9 . . . . 8.11(10) ?
C6 C7 C8 C16 . . . . -107.72(9) ?
C6 N2 C9 C10 . . . . -178.08(9) ?
C6 N2 C9 C8 . . . . 4.23(11) ?
C17 C8 C9 N2 . . . . -127.20(9) ?
C16 C8 C9 N2 . . . . 109.64(10) ?
C7 C8 C9 N2 . . . . -8.07(11) ?
C17 C8 C9 C10 . . . . 54.98(12) ?
C16 C8 C9 C10 . . . . -68.17(12) ?
C7 C8 C9 C10 . . . . 174.11(9) ?
N2 C9 C10 C1 . . . 2_666 -1.85(17) ?
C8 C9 C10 C1 . . . 2_666 175.68(9) ?
C3 C2 C11 C12 . . . . -79.12(13) ?
C1 C2 C11 C12 . . . . 97.10(11) ?
C14 O2 C13 O1 . . . . -1.87(14) ?
C14 O2 C13 C3 . . . . 177.69(8) ?
C2 C3 C13 O1 . . . . 176.60(10) ?
C4 C3 C13 O1 . . . . -3.31(15) ?
C2 C3 C13 O2 . . . . -2.94(14) ?
C4 C3 C13 O2 . . . . 177.15(8) ?
C13 O2 C14 C15 . . . . -172.60(8) ?

####################################################################### 
# 
# 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_cu_vippn_jsl_pn7_cu_0m
_database_code_depnum_ccdc_archive 'CCDC 2125372'
loop_
_audit_author_name
_audit_author_address
'Phattananawee Nalaoh'
;Vidyasirimedhi Institute of Science and Technology
Thailand
;
_audit_update_record             
;
2021-12-02 deposited with the CCDC.	2022-01-17 downloaded from the CCDC.
;
_audit_creation_date             2021-11-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H30 B N O6 S2'
_chemical_formula_sum            'C26 H30 B N O6 S2'
_chemical_formula_weight         527.44
_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'
B B 0.0090 0.0039 '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'
S S 0.3331 0.5567 '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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   13.1157(3)
_cell_length_b                   13.2742(4)
_cell_length_c                   29.9769(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5219.0(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9965
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.13
_cell_measurement_theta_min      4.48
_shelx_estimated_absorpt_T_max   0.957
_shelx_estimated_absorpt_T_min   0.343
_exptl_absorpt_coefficient_mu    2.197
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1523 before and 0.0709 after correction.
The Ratio of minimum to maximum transmission is 0.7950.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2224
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            47668
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.589
_diffrn_reflns_theta_max         66.589
_diffrn_reflns_theta_min         4.479
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_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                4222
_reflns_number_total             4592
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.759
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.214
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         4592
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0692
_refine_ls_restrained_S_all      1.214
_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)+(0.0519P)²+17.8682P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1753
_refine_ls_wR_factor_ref         0.1782
_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), C6(H6), C7(H7), C10(H10), C11(H11), C13(H13), C14(H14),
 C16(H16), C17(H17), C19(H19), C20(H20)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C8(H8A,H8B,H8C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C),
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.67367(8) 0.55835(7) 0.35789(3) 0.0300(3) Uani 1 1 d . . . . .
S2 S 0.56770(7) 0.48445(7) 0.27754(3) 0.0208(2) Uani 1 1 d . . . . .
O1 O 0.6752(3) 0.5226(2) 0.40265(10) 0.0454(9) Uani 1 1 d . . . . .
O2 O 0.7644(2) 0.5644(2) 0.33246(11) 0.0385(7) Uani 1 1 d . . . . .
O3 O 0.4602(2) 0.4676(2) 0.27312(9) 0.0266(6) Uani 1 1 d . . . . .
O4 O 0.6113(2) 0.57657(19) 0.26251(9) 0.0253(6) Uani 1 1 d . . . . .
O5 O 0.4150(2) 0.1284(2) 0.46827(10) 0.0393(8) Uani 1 1 d . . . . .
O6 O 0.2696(2) 0.2222(3) 0.45711(10) 0.0456(8) Uani 1 1 d . . . . .
N1 N 0.5930(3) 0.4775(2) 0.33209(11) 0.0256(7) Uani 1 1 d . . . . .
C1 C 0.4647(4) 0.9643(4) 0.35840(18) 0.0478(13) Uani 1 1 d . . . . .
H1A H 0.392480 0.956002 0.350781 0.072 Uiso 1 1 calc R U . . .
H1B H 0.497439 1.008118 0.336339 0.072 Uiso 1 1 calc R U . . .
H1C H 0.470477 0.994792 0.388070 0.072 Uiso 1 1 calc R U . . .
C2 C 0.5164(4) 0.8625(3) 0.35843(15) 0.0360(10) Uani 1 1 d . . . . .
C3 C 0.4802(4) 0.7845(4) 0.38505(16) 0.0450(12) Uani 1 1 d . . . . .
H3 H 0.421899 0.794984 0.403255 0.054 Uiso 1 1 calc R U . . .
C4 C 0.5282(4) 0.6920(3) 0.38527(15) 0.0412(11) Uani 1 1 d . . . . .
H4 H 0.504441 0.639620 0.404212 0.049 Uiso 1 1 calc R U . . .
C5 C 0.6123(3) 0.6759(3) 0.35730(13) 0.0279(9) Uani 1 1 d . . . . .
C6 C 0.6469(3) 0.7514(3) 0.32928(13) 0.0257(8) Uani 1 1 d . . . . .
H6 H 0.701995 0.739300 0.309422 0.031 Uiso 1 1 calc R U . . .
C7 C 0.6002(3) 0.8441(3) 0.33059(13) 0.0273(9) Uani 1 1 d . . . . .
H7 H 0.625368 0.896897 0.312222 0.033 Uiso 1 1 calc R U . . .
C8 C 0.7684(3) 0.1501(3) 0.17428(14) 0.0300(9) Uani 1 1 d . . . . .
H8A H 0.742967 0.083477 0.182943 0.045 Uiso 1 1 calc R U . . .
H8B H 0.842781 0.151643 0.177310 0.045 Uiso 1 1 calc R U . . .
H8C H 0.749704 0.163713 0.143207 0.045 Uiso 1 1 calc R U . . .
C9 C 0.7219(3) 0.2292(3) 0.20408(12) 0.0226(8) Uani 1 1 d . . . . .
C10 C 0.7737(3) 0.3197(3) 0.21231(13) 0.0240(8) Uani 1 1 d . . . . .
H10 H 0.840731 0.328541 0.200953 0.029 Uiso 1 1 calc R U . . .
C11 C 0.7290(3) 0.3962(3) 0.23659(12) 0.0219(8) Uani 1 1 d . . . . .
H11 H 0.764611 0.457310 0.242068 0.026 Uiso 1 1 calc R U . . .
C12 C 0.6313(3) 0.3819(3) 0.25279(12) 0.0205(8) Uani 1 1 d . . . . .
C13 C 0.5801(3) 0.2916(3) 0.24704(13) 0.0245(8) Uani 1 1 d . . . . .
H13 H 0.514065 0.282051 0.259338 0.029 Uiso 1 1 calc R U . . .
C14 C 0.6268(3) 0.2159(3) 0.22315(13) 0.0260(8) Uani 1 1 d . . . . .
H14 H 0.592844 0.153139 0.219692 0.031 Uiso 1 1 calc R U . . .
C15 C 0.5356(3) 0.4071(3) 0.35925(13) 0.0264(8) Uani 1 1 d . . . . .
C16 C 0.4373(3) 0.4316(3) 0.37278(14) 0.0329(10) Uani 1 1 d . . . . .
H16 H 0.406941 0.493534 0.363995 0.040 Uiso 1 1 calc R U . . .
C17 C 0.3847(3) 0.3644(3) 0.39919(15) 0.0364(10) Uani 1 1 d . . . . .
H17 H 0.317123 0.380347 0.408207 0.044 Uiso 1 1 calc R U . . .
C18 C 0.4279(3) 0.2737(3) 0.41304(13) 0.0329(10) Uani 1 1 d . . . . .
C19 C 0.5255(3) 0.2501(3) 0.39776(14) 0.0314(9) Uani 1 1 d . . . . .
H19 H 0.555660 0.187788 0.406085 0.038 Uiso 1 1 calc R U . . .
C20 C 0.5793(3) 0.3157(3) 0.37075(13) 0.0284(9) Uani 1 1 d . . . . .
H20 H 0.645308 0.298368 0.360221 0.034 Uiso 1 1 calc R U . . .
C21 C 0.3341(4) 0.0803(4) 0.49418(17) 0.0508(13) Uani 1 1 d . . . . .
C22 C 0.2984(6) -0.0084(5) 0.4666(2) 0.0703(18) Uani 1 1 d . . . . .
H22A H 0.275254 0.015455 0.437394 0.105 Uiso 1 1 calc R U . . .
H22B H 0.242028 -0.042150 0.481981 0.105 Uiso 1 1 calc R U . . .
H22C H 0.354918 -0.055854 0.462653 0.105 Uiso 1 1 calc R U . . .
C23 C 0.3763(5) 0.0444(5) 0.53751(19) 0.0625(16) Uani 1 1 d . . . . .
H23A H 0.421542 -0.013077 0.532236 0.094 Uiso 1 1 calc R U . . .
H23B H 0.320213 0.023784 0.557097 0.094 Uiso 1 1 calc R U . . .
H23C H 0.414779 0.098987 0.551697 0.094 Uiso 1 1 calc R U . . .
C24 C 0.2501(4) 0.1661(4) 0.49759(16) 0.0497(13) Uani 1 1 d . . . . .
C25 C 0.1425(4) 0.1260(6) 0.4986(2) 0.0736(19) Uani 1 1 d . . . . .
H25A H 0.094476 0.182471 0.500093 0.110 Uiso 1 1 calc R U . . .
H25B H 0.133613 0.082782 0.524753 0.110 Uiso 1 1 calc R U . . .
H25C H 0.129582 0.086863 0.471427 0.110 Uiso 1 1 calc R U . . .
C26 C 0.2690(5) 0.2363(5) 0.53707(19) 0.0632(16) Uani 1 1 d . . . . .
H26A H 0.340450 0.257748 0.537119 0.095 Uiso 1 1 calc R U . . .
H26B H 0.253797 0.200655 0.564931 0.095 Uiso 1 1 calc R U . . .
H26C H 0.224718 0.295489 0.534523 0.095 Uiso 1 1 calc R U . . .
B1 B 0.3690(4) 0.2045(4) 0.44642(16) 0.0357(11) 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
S1 O1 1.423(3) . ?
S1 O2 1.415(3) . ?
S1 N1 1.694(3) . ?
S1 C5 1.756(4) . ?
S2 O3 1.433(3) . ?
S2 O4 1.423(3) . ?
S2 N1 1.671(3) . ?
S2 C12 1.760(4) . ?
O5 C21 1.462(6) . ?
O5 B1 1.346(6) . ?
O6 C24 1.447(6) . ?
O6 B1 1.363(6) . ?
N1 C15 1.450(5) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.512(6) . ?
C2 C3 1.391(7) . ?
C2 C7 1.401(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.380(7) . ?
C4 H4 0.9500 . ?
C4 C5 1.402(6) . ?
C5 C6 1.384(6) . ?
C6 H6 0.9500 . ?
C6 C7 1.376(6) . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C8 C9 1.508(5) . ?
C9 C10 1.403(5) . ?
C9 C14 1.383(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.380(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.384(5) . ?
C12 C13 1.385(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.377(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.390(6) . ?
C15 C20 1.386(6) . ?
C16 H16 0.9500 . ?
C16 C17 1.378(6) . ?
C17 H17 0.9500 . ?
C17 C18 1.395(6) . ?
C18 C19 1.395(6) . ?
C18 B1 1.563(6) . ?
C19 H19 0.9500 . ?
C19 C20 1.382(6) . ?
C20 H20 0.9500 . ?
C21 C22 1.512(8) . ?
C21 C23 1.490(8) . ?
C21 C24 1.587(8) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C25 1.508(8) . ?
C24 C26 1.526(8) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

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
O1 S1 N1 103.20(18) . . ?
O1 S1 C5 108.2(2) . . ?
O2 S1 O1 121.0(2) . . ?
O2 S1 N1 108.38(18) . . ?
O2 S1 C5 109.21(19) . . ?
N1 S1 C5 105.77(18) . . ?
O3 S2 N1 106.10(17) . . ?
O3 S2 C12 107.86(17) . . ?
O4 S2 O3 119.96(16) . . ?
O4 S2 N1 106.10(16) . . ?
O4 S2 C12 109.92(17) . . ?
N1 S2 C12 106.03(17) . . ?
B1 O5 C21 105.1(4) . . ?
B1 O6 C24 106.1(4) . . ?
S2 N1 S1 122.4(2) . . ?
C15 N1 S1 118.4(3) . . ?
C15 N1 S2 118.8(3) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 120.8(4) . . ?
C3 C2 C7 118.7(4) . . ?
C7 C2 C1 120.5(4) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.6(4) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.4(4) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 S1 119.3(3) . . ?
C6 C5 S1 120.0(3) . . ?
C6 C5 C4 120.7(4) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 C5 119.0(4) . . ?
C7 C6 H6 120.5 . . ?
C2 C7 H7 119.3 . . ?
C6 C7 C2 121.5(4) . . ?
C6 C7 H7 119.3 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C9 C8 H8C 109.5 . . ?
C10 C9 C8 120.3(3) . . ?
C14 C9 C8 121.4(3) . . ?
C14 C9 C10 118.3(3) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.2(3) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 H11 120.7 . . ?
C10 C11 C12 118.5(3) . . ?
C12 C11 H11 120.7 . . ?
C11 C12 S2 118.8(3) . . ?
C11 C12 C13 121.6(3) . . ?
C13 C12 S2 119.5(3) . . ?
C12 C13 H13 120.6 . . ?
C14 C13 C12 118.8(3) . . ?
C14 C13 H13 120.6 . . ?
C9 C14 H14 119.3 . . ?
C13 C14 C9 121.5(3) . . ?
C13 C14 H14 119.3 . . ?
C16 C15 N1 119.6(4) . . ?
C20 C15 N1 119.3(4) . . ?
C20 C15 C16 121.1(4) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 C15 118.7(4) . . ?
C17 C16 H16 120.6 . . ?
C16 C17 H17 119.1 . . ?
C16 C17 C18 121.8(4) . . ?
C18 C17 H17 119.1 . . ?
C17 C18 C19 118.0(4) . . ?
C17 C18 B1 119.8(4) . . ?
C19 C18 B1 122.2(4) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 C18 121.3(4) . . ?
C20 C19 H19 119.4 . . ?
C15 C20 H20 120.4 . . ?
C19 C20 C15 119.1(4) . . ?
C19 C20 H20 120.4 . . ?
O5 C21 C22 105.9(4) . . ?
O5 C21 C23 109.5(4) . . ?
O5 C21 C24 103.0(4) . . ?
C22 C21 C24 112.3(5) . . ?
C23 C21 C22 110.0(5) . . ?
C23 C21 C24 115.5(5) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O6 C24 C21 101.1(4) . . ?
O6 C24 C25 111.2(5) . . ?
O6 C24 C26 107.9(5) . . ?
C25 C24 C21 113.4(5) . . ?
C25 C24 C26 110.6(5) . . ?
C26 C24 C21 112.1(5) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O5 B1 O6 116.3(4) . . ?
O5 B1 C18 122.0(4) . . ?
O6 B1 C18 121.5(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N1 C15 C16 94.7(4) . . . . ?
S1 N1 C15 C20 -86.2(4) . . . . ?
S1 C5 C6 C7 -177.5(3) . . . . ?
S2 N1 C15 C16 -78.7(4) . . . . ?
S2 N1 C15 C20 100.4(4) . . . . ?
S2 C12 C13 C14 172.7(3) . . . . ?
O1 S1 N1 S2 -177.8(2) . . . . ?
O1 S1 N1 C15 9.1(3) . . . . ?
O1 S1 C5 C4 -37.7(4) . . . . ?
O1 S1 C5 C6 142.5(3) . . . . ?
O2 S1 N1 S2 -48.3(3) . . . . ?
O2 S1 N1 C15 138.5(3) . . . . ?
O2 S1 C5 C4 -171.3(3) . . . . ?
O2 S1 C5 C6 9.0(4) . . . . ?
O3 S2 N1 S1 -138.4(2) . . . . ?
O3 S2 N1 C15 34.7(3) . . . . ?
O3 S2 C12 C11 154.4(3) . . . . ?
O3 S2 C12 C13 -20.9(4) . . . . ?
O4 S2 N1 S1 -9.8(3) . . . . ?
O4 S2 N1 C15 163.3(3) . . . . ?
O4 S2 C12 C11 21.9(3) . . . . ?
O4 S2 C12 C13 -153.4(3) . . . . ?
O5 C21 C24 O6 28.3(5) . . . . ?
O5 C21 C24 C25 147.5(5) . . . . ?
O5 C21 C24 C26 -86.4(5) . . . . ?
N1 S1 C5 C4 72.3(4) . . . . ?
N1 S1 C5 C6 -107.5(3) . . . . ?
N1 S2 C12 C11 -92.3(3) . . . . ?
N1 S2 C12 C13 92.4(3) . . . . ?
N1 C15 C16 C17 -178.9(4) . . . . ?
N1 C15 C20 C19 178.1(4) . . . . ?
C1 C2 C3 C4 -179.4(5) . . . . ?
C1 C2 C7 C6 -178.4(4) . . . . ?
C2 C3 C4 C5 -2.0(8) . . . . ?
C3 C2 C7 C6 -0.2(6) . . . . ?
C3 C4 C5 S1 179.6(4) . . . . ?
C3 C4 C5 C6 -0.6(7) . . . . ?
C4 C5 C6 C7 2.8(6) . . . . ?
C5 S1 N1 S2 68.7(3) . . . . ?
C5 S1 N1 C15 -104.4(3) . . . . ?
C5 C6 C7 C2 -2.4(6) . . . . ?
C7 C2 C3 C4 2.4(7) . . . . ?
C8 C9 C10 C11 174.9(3) . . . . ?
C8 C9 C14 C13 -174.0(4) . . . . ?
C9 C10 C11 C12 -0.1(5) . . . . ?
C10 C9 C14 C13 4.5(6) . . . . ?
C10 C11 C12 S2 -172.0(3) . . . . ?
C10 C11 C12 C13 3.2(6) . . . . ?
C11 C12 C13 C14 -2.4(6) . . . . ?
C12 S2 N1 S1 107.1(2) . . . . ?
C12 S2 N1 C15 -79.8(3) . . . . ?
C12 C13 C14 C9 -1.6(6) . . . . ?
C14 C9 C10 C11 -3.7(6) . . . . ?
C15 C16 C17 C18 0.9(7) . . . . ?
C16 C15 C20 C19 -2.9(6) . . . . ?
C16 C17 C18 C19 -2.7(6) . . . . ?
C16 C17 C18 B1 174.5(4) . . . . ?
C17 C18 C19 C20 1.8(6) . . . . ?
C17 C18 B1 O5 -165.2(4) . . . . ?
C17 C18 B1 O6 10.5(7) . . . . ?
C18 C19 C20 C15 0.9(6) . . . . ?
C19 C18 B1 O5 11.9(7) . . . . ?
C19 C18 B1 O6 -172.4(4) . . . . ?
C20 C15 C16 C17 2.0(6) . . . . ?
C21 O5 B1 O6 6.5(5) . . . . ?
C21 O5 B1 C18 -177.6(4) . . . . ?
C22 C21 C24 O6 -85.2(5) . . . . ?
C22 C21 C24 C25 34.0(6) . . . . ?
C22 C21 C24 C26 160.1(5) . . . . ?
C23 C21 C24 O6 147.6(5) . . . . ?
C23 C21 C24 C25 -93.2(6) . . . . ?
C23 C21 C24 C26 32.9(6) . . . . ?
C24 O6 B1 O5 13.2(6) . . . . ?
C24 O6 B1 C18 -162.7(4) . . . . ?
B1 O5 C21 C22 96.7(5) . . . . ?
B1 O5 C21 C23 -144.7(5) . . . . ?
B1 O5 C21 C24 -21.3(5) . . . . ?
B1 O6 C24 C21 -24.8(5) . . . . ?
B1 O6 C24 C25 -145.5(5) . . . . ?
B1 O6 C24 C26 93.0(5) . . . . ?
B1 C18 C19 C20 -175.3(4) . . . . ?

_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_I_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2120266'
loop_
_audit_author_name
_audit_author_address
'Roger D. Sommer'
;NC State University
United States of America
;
_audit_update_record             
;
2021-11-04 deposited with the CCDC.	2022-01-17 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            EtEs
_chemical_formula_moiety         'C35 H44 N4 O5'
_chemical_formula_sum            'C35 H44 N4 O5'
_chemical_formula_iupac          ?
_chemical_formula_weight         600.74

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.9883(3)
_cell_length_b                   11.3135(3)
_cell_length_c                   20.5010(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.5280(10)
_cell_angle_gamma                90
_cell_volume                     3241.26(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    221
_cell_measurement_theta_min      2.4747
_cell_measurement_theta_max      22.5254
_cell_measurement_temperature    110.(2)

_exptl_crystal_description       parallelapiped
_exptl_crystal_colour            'dark green'
_exptl_crystal_size_max          0.595
_exptl_crystal_size_mid          0.329
_exptl_crystal_size_min          0.228
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1288

_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
70331 Corrected reflections written
Estimated minimum and maximum transmission:  0.6954  0.7465
The ratio of these values is more reliable than their absolute values!
Additional spherical absorption correction applied with mu*r =  0.2000
Lambda/2 correction factor = 0.0015
;
_exptl_absorpt_correction_T_min  0.6954
_exptl_absorpt_correction_T_max  0.7465

_exptl_special_details           
;
;

_diffrn_ambient_temperature      110.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker-Nonius X8 Kappa APEX II'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            58352
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         30.51
_diffrn_reflns_theta_full        30.51
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       25

_refine_special_details          
;
The disorder in the second ester groups was modeled in tow parts, with roughly 
80:20 ratio. some bond lengths and angles were restrained to be the same in the
 two parts to be chemically reasonable. Ellipsoids for these atoms were still 
elongated after addition of RIGU and were thus further restrained with ISOR. 
Reflection 1 0 0  was omitted due to very low intensity as a result of being 
blocked by the beamstop.

Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_reflns_number_total             9892
_reflns_number_gt                7459
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_gt          0.1173
_refine_ls_wR_factor_ref         0.1296
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.027
_refine_ls_number_reflns         9892
_refine_ls_number_parameters     441
_refine_ls_number_restraints     58
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
w=1/[σ²(Fo²)+(0.0624P)²+1.0500P]
where P=(Fo²+2Fc²)/3
;

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.255
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'APEX2 v2012.4-3 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS Inc., 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 -0.00659(8) 0.80595(10) 0.21111(5) 0.0371(3) Uani d . . . 1.0 . .
O O2 -0.00644(7) 0.69152(9) 0.30068(5) 0.0274(2) Uani d . . . 1.0 . .
O O3 0.03675(6) 0.96608(8) 0.34475(4) 0.02401(19) Uani d . . . 1.0 . .
O O4 0.79359(6) 1.05214(9) 0.45823(5) 0.0261(2) Uani d . . . 1.0 . .
N N1 0.27633(7) 0.84843(10) 0.32268(5) 0.0194(2) Uani d . . . 1.0 . .
H H1 0.3179(11) 0.8898(14) 0.3457(7) 0.023 Uiso d U . . 1.0 . .
N N2 0.27504(7) 1.05975(9) 0.40375(5) 0.0186(2) Uani d . . . 1.0 . .
N N3 0.49004(7) 1.04749(9) 0.42194(5) 0.01727(19) Uani d . . . 1.0 . .
H H3 0.4468(11) 1.0028(14) 0.4039(7) 0.021 Uiso d U . . 1.0 . .
N N4 0.48715(7) 0.83127(9) 0.34306(4) 0.01735(19) Uani d . . . 1.0 . .
C C1 0.29689(9) 0.75680(11) 0.28172(6) 0.0201(2) Uani d . . . 1.0 . .
C C2 0.20769(9) 0.71682(11) 0.25259(6) 0.0210(2) Uani d . . . 1.0 . .
C C3 0.13641(9) 0.78455(11) 0.27807(6) 0.0206(2) Uani d . . . 1.0 . .
C C4 0.17953(8) 0.86879(11) 0.32191(5) 0.0192(2) Uani d . . . 1.0 . .
C C5 0.13529(8) 0.95912(11) 0.35554(6) 0.0198(2) Uani d . . . 1.0 . .
C C6 0.17987(8) 1.04923(11) 0.39254(5) 0.0192(2) Uani d . . . 1.0 . .
C C7 0.12372(9) 1.14673(12) 0.42326(6) 0.0235(2) Uani d . . . 1.0 . .
H H7A 0.0904 1.1177 0.4617 0.028 Uiso calc U . R 1.0 . .
H H7B 0.0761 1.1813 0.3915 0.028 Uiso calc U . R 1.0 . .
C C8 0.20181(9) 1.23703(11) 0.44325(6) 0.0207(2) Uani d . . . 1.0 . .
C C9 0.29266(8) 1.16296(11) 0.43636(5) 0.0188(2) Uani d . . . 1.0 . .
C C10 0.38112(8) 1.20377(11) 0.45820(5) 0.0187(2) Uani d . . . 1.0 . .
H H10 0.3807 1.2776 0.4803 0.022 Uiso calc U . R 1.0 . .
C C11 0.47170(8) 1.15262(11) 0.45266(5) 0.0178(2) Uani d . . . 1.0 . .
C C12 0.56108(9) 1.19947(10) 0.47541(5) 0.0183(2) Uani d . . . 1.0 . .
C C13 0.63177(8) 1.11998(11) 0.45718(5) 0.0186(2) Uani d . . . 1.0 . .
C C14 0.58573(8) 1.02395(10) 0.42364(5) 0.0174(2) Uani d . . . 1.0 . .
C C15 0.62711(8) 0.92340(11) 0.39656(6) 0.0193(2) Uani d . . . 1.0 . .
H H15 0.6944 0.9155 0.4035 0.023 Uiso calc U . R 1.0 . .
C C16 0.58201(8) 0.83492(11) 0.36120(5) 0.0187(2) Uani d . . . 1.0 . .
C C17 0.63435(9) 0.72759(12) 0.33726(6) 0.0247(3) Uani d . . . 1.0 . .
H H17A 0.644 0.6682 0.3724 0.03 Uiso calc U . R 1.0 . .
H H17B 0.6972 0.7495 0.3205 0.03 Uiso calc U . R 1.0 . .
C C18 0.56653(9) 0.68133(11) 0.28240(6) 0.0215(2) Uani d . . . 1.0 . .
C C19 0.47363(8) 0.74140(11) 0.30046(5) 0.0182(2) Uani d . . . 1.0 . .
C C20 0.38617(9) 0.70961(11) 0.27109(6) 0.0211(2) Uani d . . . 1.0 . .
H H20 0.3877 0.6478 0.2398 0.025 Uiso calc U . R 1.0 . .
C C21 0.19604(10) 0.61593(12) 0.20584(6) 0.0260(3) Uani d . . . 1.0 . .
H H21A 0.2485 0.618 0.175 0.031 Uiso calc U . R 1.0 . .
H H21B 0.1348 0.625 0.1802 0.031 Uiso calc U . R 1.0 . .
C C22 0.19695(12) 0.49692(14) 0.24046(8) 0.0375(3) Uani d . . . 1.0 . .
H H22A 0.1934 0.4333 0.208 0.056 Uiso calc U . R 1.0 . .
H H22B 0.1418 0.4917 0.2682 0.056 Uiso calc U . R 1.0 . .
H H22C 0.2562 0.4891 0.2675 0.056 Uiso calc U . R 1.0 . .
C C23 0.03366(9) 0.76633(12) 0.25937(6) 0.0241(3) Uani d . . . 1.0 . .
C C24 -0.10366(10) 0.65475(14) 0.28210(8) 0.0342(3) Uani d . . . 1.0 . .
H H24A -0.1071 0.6261 0.2364 0.041 Uiso calc U . R 1.0 . .
H H24B -0.1484 0.722 0.2858 0.041 Uiso calc U . R 1.0 . .
C C25 -0.12929(11) 0.55745(15) 0.32774(8) 0.0401(4) Uani d . . . 1.0 . .
H H25A -0.1938 0.5287 0.316 0.06 Uiso calc U . R 1.0 . .
H H25B -0.1274 0.5876 0.3726 0.06 Uiso calc U . R 1.0 . .
H H25C -0.0834 0.4925 0.3245 0.06 Uiso calc U . R 1.0 . .
C C26 -0.01783(10) 0.92164(14) 0.39704(7) 0.0300(3) Uani d . . . 1.0 . .
H H26A -0.0853 0.943 0.3893 0.045 Uiso calc U . R 1.0 . .
H H26B 0.0063 0.9561 0.4384 0.045 Uiso calc U . R 1.0 . .
H H26C -0.0118 0.8354 0.3991 0.045 Uiso calc U . R 1.0 . .
C C27 0.18955(10) 1.28367(13) 0.51235(6) 0.0275(3) Uani d . . . 1.0 . .
H H27A 0.1279 1.3245 0.5142 0.041 Uiso calc U . R 1.0 . .
H H27B 0.2415 1.339 0.524 0.041 Uiso calc U . R 1.0 . .
H H27C 0.1914 1.2175 0.5432 0.041 Uiso calc U . R 1.0 . .
C C28 0.20229(10) 1.33931(12) 0.39444(6) 0.0279(3) Uani d . . . 1.0 . .
H H28A 0.2076 1.3079 0.3502 0.042 Uiso calc U . R 1.0 . .
H H28B 0.2569 1.3912 0.4051 0.042 Uiso calc U . R 1.0 . .
H H28C 0.1427 1.3844 0.3968 0.042 Uiso calc U . R 1.0 . .
C C29 0.57317(9) 1.31499(11) 0.51087(6) 0.0234(2) Uani d . . . 1.0 . .
H H29A 0.6279 1.3088 0.543 0.028 Uiso calc U . R 1.0 . .
H H29B 0.515 1.3313 0.5351 0.028 Uiso calc U . R 1.0 . .
C C30 0.59056(11) 1.41760(13) 0.46455(8) 0.0328(3) Uani d . . . 1.0 . .
H H30A 0.5353 1.4262 0.4338 0.049 Uiso calc U . R 1.0 . .
H H30B 0.648 1.4018 0.4403 0.049 Uiso calc U . R 1.0 . .
H H30C 0.5995 1.4907 0.4898 0.049 Uiso calc U . R 1.0 . .
C C31 0.73610(9) 1.12959(11) 0.46674(6) 0.0211(2) Uani d . . D 1.0 . .
C C34 0.56043(10) 0.54679(12) 0.27994(8) 0.0314(3) Uani d . . . 1.0 . .
H H34A 0.5378 0.5171 0.3214 0.047 Uiso calc U . R 1.0 . .
H H34B 0.6239 0.514 0.2726 0.047 Uiso calc U . R 1.0 . .
H H34C 0.5157 0.5229 0.2442 0.047 Uiso calc U . R 1.0 . .
C C35 0.59505(11) 0.73004(14) 0.21626(7) 0.0333(3) Uani d . . . 1.0 . .
H H35A 0.5448 0.7118 0.183 0.05 Uiso calc U . R 1.0 . .
H H35B 0.6553 0.6936 0.2041 0.05 Uiso calc U . R 1.0 . .
H H35C 0.6033 0.8159 0.2194 0.05 Uiso calc U . R 1.0 . .
O O5 0.7633(3) 1.2399(3) 0.4833(3) 0.0381(10) Uani d U P D 0.826(6) A 1
C C32 0.8654(3) 1.2608(4) 0.4888(3) 0.0512(12) Uani d U P D 0.826(6) A 1
H H32A 0.8915 1.2711 0.445 0.061 Uiso calc U P R 0.826(6) A 1
H H32B 0.8986 1.1936 0.5108 0.061 Uiso calc U P R 0.826(6) A 1
C C33 0.87876(18) 1.3721(2) 0.5285(2) 0.0716(13) Uani d U P D 0.826(6) A 1
H H33A 0.8484 1.4386 0.505 0.107 Uiso calc U P R 0.826(6) A 1
H H33B 0.9473 1.3881 0.5359 0.107 Uiso calc U P R 0.826(6) A 1
H H33C 0.8492 1.3621 0.5707 0.107 Uiso calc U P R 0.826(6) A 1
O O5A 0.7588(16) 1.2340(14) 0.4945(14) 0.038(4) Uani d U P D 0.174(6) A 2
C C32A 0.8578(15) 1.264(2) 0.5074(10) 0.037(4) Uani d U P D 0.174(6) A 2
H H32C 0.8984 1.194 0.4991 0.045 Uiso calc U P R 0.174(6) A 2
H H32D 0.8683 1.2867 0.5538 0.045 Uiso calc U P R 0.174(6) A 2
C C33A 0.8844(8) 1.3637(15) 0.4641(10) 0.082(6) Uani d U P D 0.174(6) A 2
H H33D 0.8766 1.3391 0.4183 0.123 Uiso calc U P R 0.174(6) A 2
H H33E 0.9512 1.386 0.4739 0.123 Uiso calc U P R 0.174(6) A 2
H H33F 0.8428 1.4315 0.4717 0.123 Uiso calc U P R 0.174(6) A 2


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C23 . 1.2031(16) ?
O2 C23 . 1.3379(16) ?
O2 C24 . 1.4568(16) ?
O3 C5 . 1.3887(14) ?
O3 C26 . 1.4343(15) ?
O4 C31 . 1.2071(15) ?
N1 C1 . 1.3726(15) ?
N1 C4 . 1.3729(15) ?
N1 H1 . 0.869(16) ?
N2 C6 . 1.3462(15) ?
N2 C9 . 1.3627(16) ?
N3 C14 . 1.3638(15) ?
N3 C11 . 1.3753(15) ?
N3 H3 . 0.859(16) ?
N4 C19 . 1.3482(15) ?
N4 C16 . 1.3627(15) ?
C1 C20 . 1.3842(17) ?
C1 C2 . 1.4326(17) ?
C2 C3 . 1.3785(17) ?
C2 C21 . 1.4947(17) ?
C3 C4 . 1.4255(17) ?
C3 C23 . 1.4855(17) ?
C4 C5 . 1.3929(16) ?
C5 C6 . 1.4007(17) ?
C6 C7 . 1.5079(16) ?
C7 C8 . 1.5380(18) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C8 C27 . 1.5285(16) ?
C8 C28 . 1.5301(18) ?
C8 C9 . 1.5340(16) ?
C9 C10 . 1.3769(17) ?
C10 C11 . 1.4020(16) ?
C10 H10 . 0.95 ?
C11 C12 . 1.4179(17) ?
C12 C13 . 1.3996(16) ?
C12 C29 . 1.5013(17) ?
C13 C14 . 1.4245(16) ?
C13 C31 . 1.4679(17) ?
C14 C15 . 1.4020(16) ?
C15 C16 . 1.3731(17) ?
C15 H15 . 0.95 ?
C16 C17 . 1.5110(16) ?
C17 C18 . 1.5313(18) ?
C17 H17A . 0.99 ?
C17 H17B . 0.99 ?
C18 C34 . 1.5252(19) ?
C18 C19 . 1.5265(16) ?
C18 C35 . 1.5328(18) ?
C19 C20 . 1.3869(17) ?
C20 H20 . 0.95 ?
C21 C22 . 1.522(2) ?
C21 H21A . 0.99 ?
C21 H21B . 0.99 ?
C22 H22A . 0.98 ?
C22 H22B . 0.98 ?
C22 H22C . 0.98 ?
C24 C25 . 1.498(2) ?
C24 H24A . 0.99 ?
C24 H24B . 0.99 ?
C25 H25A . 0.98 ?
C25 H25B . 0.98 ?
C25 H25C . 0.98 ?
C26 H26A . 0.98 ?
C26 H26B . 0.98 ?
C26 H26C . 0.98 ?
C27 H27A . 0.98 ?
C27 H27B . 0.98 ?
C27 H27C . 0.98 ?
C28 H28A . 0.98 ?
C28 H28B . 0.98 ?
C28 H28C . 0.98 ?
C29 C30 . 1.5260(19) ?
C29 H29A . 0.99 ?
C29 H29B . 0.99 ?
C30 H30A . 0.98 ?
C30 H30B . 0.98 ?
C30 H30C . 0.98 ?
C31 O5A . 1.344(9) ?
C31 O5 . 1.344(2) ?
C34 H34A . 0.98 ?
C34 H34B . 0.98 ?
C34 H34C . 0.98 ?
C35 H35A . 0.98 ?
C35 H35B . 0.98 ?
C35 H35C . 0.98 ?
O5 C32 . 1.448(4) ?
C32 C33 . 1.507(5) ?
C32 H32A . 0.99 ?
C32 H32B . 0.99 ?
C33 H33A . 0.98 ?
C33 H33B . 0.98 ?
C33 H33C . 0.98 ?
O5A C32A . 1.437(15) ?
C32A C33A . 1.496(16) ?
C32A H32C . 0.99 ?
C32A H32D . 0.99 ?
C33A H33D . 0.98 ?
C33A H33E . 0.98 ?
C33A H33F . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C23 O2 C24 . . 115.32(11) ?
C5 O3 C26 . . 114.73(10) ?
C1 N1 C4 . . 110.66(10) ?
C1 N1 H1 . . 125.8(10) ?
C4 N1 H1 . . 123.5(10) ?
C6 N2 C9 . . 108.40(10) ?
C14 N3 C11 . . 111.10(10) ?
C14 N3 H3 . . 124.6(10) ?
C11 N3 H3 . . 124.3(10) ?
C19 N4 C16 . . 107.86(10) ?
N1 C1 C20 . . 127.05(11) ?
N1 C1 C2 . . 106.94(10) ?
C20 C1 C2 . . 126.00(11) ?
C3 C2 C1 . . 107.33(11) ?
C3 C2 C21 . . 127.39(11) ?
C1 C2 C21 . . 125.22(11) ?
C2 C3 C4 . . 108.52(11) ?
C2 C3 C23 . . 122.20(11) ?
C4 C3 C23 . . 129.28(11) ?
N1 C4 C5 . . 125.23(11) ?
N1 C4 C3 . . 106.55(10) ?
C5 C4 C3 . . 128.15(11) ?
O3 C5 C4 . . 114.98(11) ?
O3 C5 C6 . . 117.39(10) ?
C4 C5 C6 . . 127.24(11) ?
N2 C6 C5 . . 124.75(11) ?
N2 C6 C7 . . 113.18(11) ?
C5 C6 C7 . . 122.07(11) ?
C6 C7 C8 . . 102.72(10) ?
C6 C7 H7A . . 111.2 ?
C8 C7 H7A . . 111.2 ?
C6 C7 H7B . . 111.2 ?
C8 C7 H7B . . 111.2 ?
H7A C7 H7B . . 109.1 ?
C27 C8 C28 . . 110.43(11) ?
C27 C8 C9 . . 113.65(10) ?
C28 C8 C9 . . 108.99(10) ?
C27 C8 C7 . . 111.65(10) ?
C28 C8 C7 . . 110.59(10) ?
C9 C8 C7 . . 101.20(10) ?
N2 C9 C10 . . 125.97(11) ?
N2 C9 C8 . . 112.37(10) ?
C10 C9 C8 . . 121.55(11) ?
C9 C10 C11 . . 129.62(11) ?
C9 C10 H10 . . 115.2 ?
C11 C10 H10 . . 115.2 ?
N3 C11 C10 . . 125.56(11) ?
N3 C11 C12 . . 107.12(10) ?
C10 C11 C12 . . 127.30(11) ?
C13 C12 C11 . . 107.16(10) ?
C13 C12 C29 . . 128.52(11) ?
C11 C12 C29 . . 124.30(11) ?
C12 C13 C14 . . 108.02(10) ?
C12 C13 C31 . . 128.81(11) ?
C14 C13 C31 . . 123.13(10) ?
N3 C14 C15 . . 124.77(11) ?
N3 C14 C13 . . 106.60(10) ?
C15 C14 C13 . . 128.63(11) ?
C16 C15 C14 . . 127.77(11) ?
C16 C15 H15 . . 116.1 ?
C14 C15 H15 . . 116.1 ?
N4 C16 C15 . . 125.83(11) ?
N4 C16 C17 . . 111.53(10) ?
C15 C16 C17 . . 122.64(11) ?
C16 C17 C18 . . 102.70(10) ?
C16 C17 H17A . . 111.2 ?
C18 C17 H17A . . 111.2 ?
C16 C17 H17B . . 111.2 ?
C18 C17 H17B . . 111.2 ?
H17A C17 H17B . . 109.1 ?
C34 C18 C19 . . 113.91(11) ?
C34 C18 C17 . . 113.41(11) ?
C19 C18 C17 . . 100.15(9) ?
C34 C18 C35 . . 110.24(11) ?
C19 C18 C35 . . 108.18(11) ?
C17 C18 C35 . . 110.48(11) ?
N4 C19 C20 . . 124.93(11) ?
N4 C19 C18 . . 113.34(10) ?
C20 C19 C18 . . 121.56(10) ?
C1 C20 C19 . . 128.05(11) ?
C1 C20 H20 . . 116.0 ?
C19 C20 H20 . . 116.0 ?
C2 C21 C22 . . 112.21(11) ?
C2 C21 H21A . . 109.2 ?
C22 C21 H21A . . 109.2 ?
C2 C21 H21B . . 109.2 ?
C22 C21 H21B . . 109.2 ?
H21A C21 H21B . . 107.9 ?
C21 C22 H22A . . 109.5 ?
C21 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C21 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
O1 C23 O2 . . 124.21(12) ?
O1 C23 C3 . . 124.95(12) ?
O2 C23 C3 . . 110.63(11) ?
O2 C24 C25 . . 107.03(13) ?
O2 C24 H24A . . 110.3 ?
C25 C24 H24A . . 110.3 ?
O2 C24 H24B . . 110.3 ?
C25 C24 H24B . . 110.3 ?
H24A C24 H24B . . 108.6 ?
C24 C25 H25A . . 109.5 ?
C24 C25 H25B . . 109.5 ?
H25A C25 H25B . . 109.5 ?
C24 C25 H25C . . 109.5 ?
H25A C25 H25C . . 109.5 ?
H25B C25 H25C . . 109.5 ?
O3 C26 H26A . . 109.5 ?
O3 C26 H26B . . 109.5 ?
H26A C26 H26B . . 109.5 ?
O3 C26 H26C . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 109.5 ?
C8 C27 H27A . . 109.5 ?
C8 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
C8 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
C8 C28 H28A . . 109.5 ?
C8 C28 H28B . . 109.5 ?
H28A C28 H28B . . 109.5 ?
C8 C28 H28C . . 109.5 ?
H28A C28 H28C . . 109.5 ?
H28B C28 H28C . . 109.5 ?
C12 C29 C30 . . 112.25(11) ?
C12 C29 H29A . . 109.2 ?
C30 C29 H29A . . 109.2 ?
C12 C29 H29B . . 109.2 ?
C30 C29 H29B . . 109.2 ?
H29A C29 H29B . . 107.9 ?
C29 C30 H30A . . 109.5 ?
C29 C30 H30B . . 109.5 ?
H30A C30 H30B . . 109.5 ?
C29 C30 H30C . . 109.5 ?
H30A C30 H30C . . 109.5 ?
H30B C30 H30C . . 109.5 ?
O4 C31 O5A . . 123.6(11) ?
O4 C31 O5 . . 121.9(2) ?
O4 C31 C13 . . 126.27(12) ?
O5A C31 C13 . . 109.7(10) ?
O5 C31 C13 . . 111.8(2) ?
C18 C34 H34A . . 109.5 ?
C18 C34 H34B . . 109.5 ?
H34A C34 H34B . . 109.5 ?
C18 C34 H34C . . 109.5 ?
H34A C34 H34C . . 109.5 ?
H34B C34 H34C . . 109.5 ?
C18 C35 H35A . . 109.5 ?
C18 C35 H35B . . 109.5 ?
H35A C35 H35B . . 109.5 ?
C18 C35 H35C . . 109.5 ?
H35A C35 H35C . . 109.5 ?
H35B C35 H35C . . 109.5 ?
C31 O5 C32 . . 116.0(3) ?
O5 C32 C33 . . 106.1(3) ?
O5 C32 H32A . . 110.5 ?
C33 C32 H32A . . 110.5 ?
O5 C32 H32B . . 110.5 ?
C33 C32 H32B . . 110.5 ?
H32A C32 H32B . . 108.7 ?
C32 C33 H33A . . 109.5 ?
C32 C33 H33B . . 109.5 ?
H33A C33 H33B . . 109.5 ?
C32 C33 H33C . . 109.5 ?
H33A C33 H33C . . 109.5 ?
H33B C33 H33C . . 109.5 ?
C31 O5A C32A . . 119.4(18) ?
O5A C32A C33A . . 109.2(15) ?
O5A C32A H32C . . 109.8 ?
C33A C32A H32C . . 109.8 ?
O5A C32A H32D . . 109.8 ?
C33A C32A H32D . . 109.8 ?
H32C C32A H32D . . 108.3 ?
C32A C33A H33D . . 109.5 ?
C32A C33A H33E . . 109.5 ?
H33D C33A H33E . . 109.5 ?
C32A C33A H33F . . 109.5 ?
H33D C33A H33F . . 109.5 ?
H33E C33A H33F . . 109.5 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C4 N1 C1 C20 . . . . -178.35(12) ?
C4 N1 C1 C2 . . . . 0.48(13) ?
N1 C1 C2 C3 . . . . -1.10(14) ?
C20 C1 C2 C3 . . . . 177.75(12) ?
N1 C1 C2 C21 . . . . -178.34(12) ?
C20 C1 C2 C21 . . . . 0.5(2) ?
C1 C2 C3 C4 . . . . 1.29(14) ?
C21 C2 C3 C4 . . . . 178.46(12) ?
C1 C2 C3 C23 . . . . -179.14(11) ?
C21 C2 C3 C23 . . . . -2.0(2) ?
C1 N1 C4 C5 . . . . -176.73(11) ?
C1 N1 C4 C3 . . . . 0.31(13) ?
C2 C3 C4 N1 . . . . -1.01(14) ?
C23 C3 C4 N1 . . . . 179.46(12) ?
C2 C3 C4 C5 . . . . 175.91(12) ?
C23 C3 C4 C5 . . . . -3.6(2) ?
C26 O3 C5 C4 . . . . 103.98(13) ?
C26 O3 C5 C6 . . . . -82.65(14) ?
N1 C4 C5 O3 . . . . 176.87(10) ?
C3 C4 C5 O3 . . . . 0.48(18) ?
N1 C4 C5 C6 . . . . 4.3(2) ?
C3 C4 C5 C6 . . . . -172.12(12) ?
C9 N2 C6 C5 . . . . 174.58(11) ?
C9 N2 C6 C7 . . . . -4.50(13) ?
O3 C5 C6 N2 . . . . -175.39(10) ?
C4 C5 C6 N2 . . . . -2.9(2) ?
O3 C5 C6 C7 . . . . 3.60(17) ?
C4 C5 C6 C7 . . . . 176.05(12) ?
N2 C6 C7 C8 . . . . 12.27(13) ?
C5 C6 C7 C8 . . . . -166.83(11) ?
C6 C7 C8 C27 . . . . -134.91(11) ?
C6 C7 C8 C28 . . . . 101.71(11) ?
C6 C7 C8 C9 . . . . -13.68(11) ?
C6 N2 C9 C10 . . . . 178.10(11) ?
C6 N2 C9 C8 . . . . -5.65(13) ?
C27 C8 C9 N2 . . . . 132.54(11) ?
C28 C8 C9 N2 . . . . -103.85(12) ?
C7 C8 C9 N2 . . . . 12.72(12) ?
C27 C8 C9 C10 . . . . -51.02(16) ?
C28 C8 C9 C10 . . . . 72.60(14) ?
C7 C8 C9 C10 . . . . -170.84(11) ?
N2 C9 C10 C11 . . . . 0.3(2) ?
C8 C9 C10 C11 . . . . -175.68(11) ?
C14 N3 C11 C10 . . . . 178.42(11) ?
C14 N3 C11 C12 . . . . 0.06(12) ?
C9 C10 C11 N3 . . . . 1.1(2) ?
C9 C10 C11 C12 . . . . 179.09(12) ?
N3 C11 C12 C13 . . . . 0.21(12) ?
C10 C11 C12 C13 . . . . -178.11(11) ?
N3 C11 C12 C29 . . . . 178.93(10) ?
C10 C11 C12 C29 . . . . 0.61(19) ?
C11 C12 C13 C14 . . . . -0.39(13) ?
C29 C12 C13 C14 . . . . -179.04(11) ?
C11 C12 C13 C31 . . . . 177.34(11) ?
C29 C12 C13 C31 . . . . -1.3(2) ?
C11 N3 C14 C15 . . . . 179.93(11) ?
C11 N3 C14 C13 . . . . -0.30(12) ?
C12 C13 C14 N3 . . . . 0.43(13) ?
C31 C13 C14 N3 . . . . -177.46(10) ?
C12 C13 C14 C15 . . . . -179.82(11) ?
C31 C13 C14 C15 . . . . 2.30(19) ?
N3 C14 C15 C16 . . . . 3.70(19) ?
C13 C14 C15 C16 . . . . -176.02(12) ?
C19 N4 C16 C15 . . . . 170.16(11) ?
C19 N4 C16 C17 . . . . -9.67(13) ?
C14 C15 C16 N4 . . . . 3.2(2) ?
C14 C15 C16 C17 . . . . -177.00(12) ?
N4 C16 C17 C18 . . . . 19.46(13) ?
C15 C16 C17 C18 . . . . -160.39(11) ?
C16 C17 C18 C34 . . . . -141.26(11) ?
C16 C17 C18 C19 . . . . -19.50(12) ?
C16 C17 C18 C35 . . . . 94.40(12) ?
C16 N4 C19 C20 . . . . 179.93(11) ?
C16 N4 C19 C18 . . . . -4.70(13) ?
C34 C18 C19 N4 . . . . 137.56(12) ?
C17 C18 C19 N4 . . . . 16.17(13) ?
C35 C18 C19 N4 . . . . -99.49(12) ?
C34 C18 C19 C20 . . . . -46.89(16) ?
C17 C18 C19 C20 . . . . -168.29(11) ?
C35 C18 C19 C20 . . . . 76.06(15) ?
N1 C1 C20 C19 . . . . 2.1(2) ?
C2 C1 C20 C19 . . . . -176.55(12) ?
N4 C19 C20 C1 . . . . -4.1(2) ?
C18 C19 C20 C1 . . . . -179.07(12) ?
C3 C2 C21 C22 . . . . -95.99(16) ?
C1 C2 C21 C22 . . . . 80.69(16) ?
C24 O2 C23 O1 . . . . 2.75(19) ?
C24 O2 C23 C3 . . . . -172.11(11) ?
C2 C3 C23 O1 . . . . -82.57(18) ?
C4 C3 C23 O1 . . . . 96.90(17) ?
C2 C3 C23 O2 . . . . 92.24(14) ?
C4 C3 C23 O2 . . . . -88.28(16) ?
C23 O2 C24 C25 . . . . 170.83(11) ?
C13 C12 C29 C30 . . . . 86.27(15) ?
C11 C12 C29 C30 . . . . -92.16(14) ?
C12 C13 C31 O4 . . . . 169.25(12) ?
C14 C13 C31 O4 . . . . -13.32(19) ?
C12 C13 C31 O5A . . . . -3.1(14) ?
C14 C13 C31 O5A . . . . 174.3(14) ?
C12 C13 C31 O5 . . . . -14.3(3) ?
C14 C13 C31 O5 . . . . 163.1(3) ?
O4 C31 O5 C32 . . . . 1.4(6) ?
O5A C31 O5 C32 . . . . 104.(7) ?
C13 C31 O5 C32 . . . . -175.3(4) ?
C31 O5 C32 C33 . . . . -161.3(5) ?
O4 C31 O5A C32A . . . . 9.(3) ?
O5 C31 O5A C32A . . . . -76.(6) ?
C13 C31 O5A C32A . . . . -178.9(18) ?
C31 O5A C32A C33A . . . . 112.(3) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 N2 . 0.869(16) 2.353(16) 2.9121(14) 122.3(13) ?
N1 H1 N4 . 0.869(16) 2.461(16) 2.9666(14) 117.7(12) ?
N3 H3 N2 . 0.859(16) 2.487(15) 3.0174(14) 120.7(12) ?
N3 H3 N4 . 0.859(16) 2.388(15) 2.9317(14) 121.6(12) ?
C15 H15 O4 . 0.95 2.33 2.9804(15) 125.1 ?
C25 H25C O1 2_545 0.98 2.58 3.532(2) 164.2 ?
C26 H26A O4 1_455 0.98 2.57 3.3172(16) 133.1 ?
C26 H26C O2 . 0.98 2.6 3.2762(18) 126.6 ?

