# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_z1
_database_code_depnum_ccdc_archive 'CCDC 2174132'
loop_
_audit_author_name
_audit_author_address
'Yao-Fu Zeng'
;Univerisity of South China
China
;
_audit_update_record             
;
2022-05-22 deposited with the CCDC.	2022-08-22 downloaded from the CCDC.
;
_audit_creation_date             2022-04-08
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H18 N2 O8'
_chemical_formula_sum            'C14 H18 N2 O8'
_chemical_formula_weight         342.30
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.309(2)
_cell_length_b                   9.725(3)
_cell_length_c                   13.99(2)
_cell_angle_alpha                72.28(3)
_cell_angle_beta                 86.43(3)
_cell_angle_gamma                86.25(3)
_cell_volume                     815(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2775
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      22.81
_cell_measurement_theta_min      3.04
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.7051
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0667 before and 0.0603 after correction.
The Ratio of minimum to maximum transmission is 0.9462.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_av_unetI/netI     0.0528
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13836
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.042
_diffrn_reflns_theta_max         25.042
_diffrn_reflns_theta_min         3.036
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1698
_reflns_number_total             2867
_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-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2867
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1103
_refine_ls_R_factor_gt           0.0504
_refine_ls_restrained_S_all      1.035
_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)+(0.0522P)²+0.2146P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1307
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.9208(3) 0.75219(18) 0.22293(15) 0.0659(5) Uani 1 1 d . . . . .
O2 O 0.6342(3) 0.85169(18) 0.08272(14) 0.0682(6) Uani 1 1 d . . . . .
O3 O 0.3579(3) 0.67712(19) 0.04643(13) 0.0650(5) Uani 1 1 d . . . . .
O4 O 0.3221(4) 0.3603(2) 0.44602(18) 0.0833(7) Uani 1 1 d . . . . .
O5 O 0.5455(4) 0.3332(2) 0.56171(17) 0.0988(8) Uani 1 1 d . . . . .
O6 O 0.6503(3) 0.26175(17) 0.43293(12) 0.0545(5) Uani 1 1 d . . . . .
O7 O 1.0671(4) 0.1530(3) 0.3721(2) 0.1071(9) Uani 1 1 d . . . . .
O8 O 1.0470(3) 0.2510(2) 0.21433(18) 0.0852(7) Uani 1 1 d . . . . .
N1 N 0.4884(5) 0.3256(2) 0.4841(2) 0.0651(7) Uani 1 1 d . . . . .
N2 N 0.9693(4) 0.1882(3) 0.2960(2) 0.0596(6) Uani 1 1 d . . . . .
C1 C 0.6213(4) 0.4251(2) 0.26233(17) 0.0394(6) Uani 1 1 d . . . . .
C2 C 0.4788(4) 0.4763(3) 0.18698(17) 0.0455(6) Uani 1 1 d . . . . .
H2 H 0.376467 0.416903 0.178507 0.055 Uiso 1 1 calc R U . . .
C3 C 0.4896(4) 0.6172(3) 0.12398(18) 0.0469(6) Uani 1 1 d . . . . .
C4 C 0.6382(4) 0.7075(3) 0.13833(18) 0.0484(6) Uani 1 1 d . . . . .
C5 C 0.7812(4) 0.6551(3) 0.21466(19) 0.0474(6) Uani 1 1 d . . . . .
C6 C 0.7729(4) 0.5133(3) 0.27678(18) 0.0456(6) Uani 1 1 d . . . . .
H6 H 0.868195 0.477801 0.327681 0.055 Uiso 1 1 calc R U . . .
C7 C 0.6002(4) 0.2721(2) 0.33120(16) 0.0430(6) Uani 1 1 d . . . . .
H7 H 0.451361 0.248177 0.332515 0.052 Uiso 1 1 calc R U . . .
C8 C 0.7384(4) 0.1527(2) 0.30442(17) 0.0432(6) Uani 1 1 d . . . . .
C9 C 0.6909(5) -0.0009(3) 0.3709(2) 0.0636(8) Uani 1 1 d . . . . .
H9A H 0.814167 -0.067945 0.381675 0.076 Uiso 1 1 calc R U . . .
H9B H 0.614408 -0.004306 0.433841 0.076 Uiso 1 1 calc R U . . .
C10 C 0.5494(5) -0.0122(3) 0.2888(2) 0.0734(9) Uani 1 1 d . . . . .
H10A H 0.571650 -0.102283 0.272532 0.088 Uiso 1 1 calc R U . . .
H10B H 0.399515 0.008483 0.301237 0.088 Uiso 1 1 calc R U . . .
C11 C 0.6615(4) 0.1145(3) 0.2144(2) 0.0584(7) Uani 1 1 d . . . . .
H11A H 0.565493 0.187600 0.173283 0.070 Uiso 1 1 calc R U . . .
H11B H 0.775107 0.085508 0.173481 0.070 Uiso 1 1 calc R U . . .
C12 C 1.0695(5) 0.7053(3) 0.3007(2) 0.0731(9) Uani 1 1 d . . . . .
H12A H 1.157646 0.625836 0.291206 0.110 Uiso 1 1 calc R U . . .
H12B H 0.993989 0.675035 0.364778 0.110 Uiso 1 1 calc R U . . .
H12C H 1.156774 0.783602 0.298449 0.110 Uiso 1 1 calc R U . . .
C13 C 0.7618(5) 0.8861(3) -0.0078(2) 0.0846(10) Uani 1 1 d . . . . .
H13A H 0.725112 0.827836 -0.048098 0.127 Uiso 1 1 calc R U . . .
H13B H 0.909056 0.867413 0.007657 0.127 Uiso 1 1 calc R U . . .
H13C H 0.737610 0.986445 -0.044085 0.127 Uiso 1 1 calc R U . . .
C14 C 0.2019(4) 0.5879(3) 0.0305(2) 0.0669(8) Uani 1 1 d . . . . .
H14A H 0.126591 0.639049 -0.028476 0.100 Uiso 1 1 calc R U . . .
H14B H 0.103593 0.563154 0.087555 0.100 Uiso 1 1 calc R U . . .
H14C H 0.270334 0.501222 0.021530 0.100 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
O1 C5 1.367(3) . ?
O1 C12 1.429(3) . ?
O2 C4 1.380(3) . ?
O2 C13 1.419(4) . ?
O3 C3 1.368(3) . ?
O3 C14 1.425(4) . ?
O4 N1 1.188(3) . ?
O5 N1 1.191(3) . ?
O6 N1 1.427(3) . ?
O6 C7 1.450(3) . ?
O7 N2 1.211(3) . ?
O8 N2 1.210(3) . ?
N2 C8 1.508(4) . ?
C1 C2 1.381(3) . ?
C1 C6 1.388(3) . ?
C1 C7 1.516(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.388(4) . ?
C3 C4 1.389(4) . ?
C4 C5 1.394(4) . ?
C5 C6 1.390(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9800 . ?
C7 C8 1.530(3) . ?
C8 C9 1.538(4) . ?
C8 C11 1.532(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.532(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.531(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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
C5 O1 C12 118.0(2) . . ?
C4 O2 C13 115.8(2) . . ?
C3 O3 C14 117.1(2) . . ?
N1 O6 C7 113.5(2) . . ?
O4 N1 O5 130.1(3) . . ?
O4 N1 O6 117.9(3) . . ?
O5 N1 O6 111.9(3) . . ?
O7 N2 C8 117.8(3) . . ?
O8 N2 O7 123.3(3) . . ?
O8 N2 C8 118.9(2) . . ?
C2 C1 C6 120.9(2) . . ?
C2 C1 C7 117.8(2) . . ?
C6 C1 C7 121.3(2) . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.5(2) . . ?
C3 C2 H2 120.3 . . ?
O3 C3 C2 123.9(2) . . ?
O3 C3 C4 115.7(2) . . ?
C2 C3 C4 120.4(2) . . ?
O2 C4 C3 120.3(2) . . ?
O2 C4 C5 119.7(2) . . ?
C3 C4 C5 119.8(2) . . ?
O1 C5 C4 115.4(2) . . ?
O1 C5 C6 124.7(2) . . ?
C6 C5 C4 119.9(2) . . ?
C1 C6 C5 119.6(2) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
O6 C7 C1 110.89(19) . . ?
O6 C7 H7 107.6 . . ?
O6 C7 C8 105.50(18) . . ?
C1 C7 H7 107.6 . . ?
C1 C7 C8 117.2(2) . . ?
C8 C7 H7 107.6 . . ?
N2 C8 C7 109.8(2) . . ?
N2 C8 C9 114.8(2) . . ?
N2 C8 C11 114.6(2) . . ?
C7 C8 C9 114.1(2) . . ?
C7 C8 C11 113.3(2) . . ?
C11 C8 C9 88.9(2) . . ?
C8 C9 H9A 114.0 . . ?
C8 C9 H9B 114.0 . . ?
H9A C9 H9B 111.2 . . ?
C10 C9 C8 87.9(2) . . ?
C10 C9 H9A 114.0 . . ?
C10 C9 H9B 114.0 . . ?
C9 C10 H10A 113.8 . . ?
C9 C10 H10B 113.8 . . ?
H10A C10 H10B 111.0 . . ?
C11 C10 C9 89.2(2) . . ?
C11 C10 H10A 113.8 . . ?
C11 C10 H10B 113.8 . . ?
C8 C11 H11A 114.0 . . ?
C8 C11 H11B 114.0 . . ?
C10 C11 C8 88.1(2) . . ?
C10 C11 H11A 114.0 . . ?
C10 C11 H11B 114.0 . . ?
H11A C11 H11B 111.2 . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C5 C6 C1 178.8(2) . . . . ?
O2 C4 C5 O1 -4.9(3) . . . . ?
O2 C4 C5 C6 174.2(2) . . . . ?
O3 C3 C4 O2 6.0(3) . . . . ?
O3 C3 C4 C5 -179.0(2) . . . . ?
O6 C7 C8 N2 -68.3(2) . . . . ?
O6 C7 C8 C9 62.3(3) . . . . ?
O6 C7 C8 C11 162.10(19) . . . . ?
O7 N2 C8 C7 85.6(3) . . . . ?
O7 N2 C8 C9 -44.6(3) . . . . ?
O7 N2 C8 C11 -145.5(3) . . . . ?
O8 N2 C8 C7 -93.8(3) . . . . ?
O8 N2 C8 C9 136.0(2) . . . . ?
O8 N2 C8 C11 35.1(3) . . . . ?
N1 O6 C7 C1 73.7(2) . . . . ?
N1 O6 C7 C8 -158.44(18) . . . . ?
N2 C8 C9 C10 -135.1(2) . . . . ?
N2 C8 C11 C10 135.3(2) . . . . ?
C1 C2 C3 O3 179.0(2) . . . . ?
C1 C2 C3 C4 -1.9(3) . . . . ?
C1 C7 C8 N2 55.7(3) . . . . ?
C1 C7 C8 C9 -173.7(2) . . . . ?
C1 C7 C8 C11 -73.9(3) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
C2 C1 C7 O6 -144.0(2) . . . . ?
C2 C1 C7 C8 94.8(3) . . . . ?
C2 C3 C4 O2 -173.1(2) . . . . ?
C2 C3 C4 C5 1.8(4) . . . . ?
C3 C4 C5 O1 -179.9(2) . . . . ?
C3 C4 C5 C6 -0.8(4) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C6 C1 C2 C3 1.0(3) . . . . ?
C6 C1 C7 O6 33.4(3) . . . . ?
C6 C1 C7 C8 -87.8(3) . . . . ?
C7 O6 N1 O4 10.7(3) . . . . ?
C7 O6 N1 O5 -170.4(2) . . . . ?
C7 C1 C2 C3 178.4(2) . . . . ?
C7 C1 C6 C5 -177.2(2) . . . . ?
C7 C8 C9 C10 96.8(2) . . . . ?
C7 C8 C11 C10 -97.6(2) . . . . ?
C8 C9 C10 C11 18.34(19) . . . . ?
C9 C8 C11 C10 18.3(2) . . . . ?
C9 C10 C11 C8 -18.41(19) . . . . ?
C11 C8 C9 C10 -18.33(19) . . . . ?
C12 O1 C5 C4 179.2(2) . . . . ?
C12 O1 C5 C6 0.1(3) . . . . ?
C13 O2 C4 C3 -91.8(3) . . . . ?
C13 O2 C4 C5 93.3(3) . . . . ?
C14 O3 C3 C2 -0.2(3) . . . . ?
C14 O3 C3 C4 -179.2(2) . . . . ?

_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_z2
_database_code_depnum_ccdc_archive 'CCDC 2174133'
loop_
_audit_author_name
_audit_author_address
'Yao-Fu Zeng'
;Univerisity of South China
China
;
_audit_update_record             
;
2022-05-22 deposited with the CCDC.	2022-08-22 downloaded from the CCDC.
;
_audit_creation_date             2022-04-08
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H15 N O3'
_chemical_formula_sum            'C16 H15 N O3'
_chemical_formula_weight         269.29
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.438(3)
_cell_length_b                   11.990(3)
_cell_length_c                   12.647(4)
_cell_angle_alpha                74.614(7)
_cell_angle_beta                 89.797(7)
_cell_angle_gamma                77.565(7)
_cell_volume                     1345.4(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6290
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      22.72
_cell_measurement_theta_min      2.70
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.7029
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0806 before and 0.0752 after correction.
The Ratio of minimum to maximum transmission is 0.9432.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0972
_diffrn_reflns_av_unetI/netI     0.0712
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            44711
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.317
_diffrn_reflns_theta_min         1.673
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2637
_reflns_number_total             4868
_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-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.025(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         4868
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1332
_refine_ls_R_factor_gt           0.0557
_refine_ls_restrained_S_all      0.987
_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)+(0.0712P)²+0.3986P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1203
_refine_ls_wR_factor_ref         0.1587
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C31(H31A,H31B), C32(H32A,H32B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C25(H25), C26(H26),
  C27(H27), C28(H28), C29(H29)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4080(2) 0.68810(16) 0.78012(14) 0.0590(6) Uani 1 1 d . . . . .
H1 H 0.430196 0.616845 0.785073 0.089 Uiso 1 1 calc R U . . .
O2 O 0.5103(2) 0.53974(19) 0.6511(2) 0.0749(7) Uani 1 1 d . . . . .
O3 O 0.6244(3) 0.6136(2) 0.5124(2) 0.0879(8) Uani 1 1 d . . . . .
N1 N 0.5390(3) 0.6240(2) 0.5837(2) 0.0563(7) Uani 1 1 d . . . . .
C1 C 0.2913(3) 0.8799(2) 0.6741(2) 0.0417(7) Uani 1 1 d . . . . .
C2 C 0.1864(3) 0.9565(2) 0.5969(2) 0.0508(8) Uani 1 1 d . . . . .
H2 H 0.145888 0.928085 0.545318 0.061 Uiso 1 1 calc R U . . .
C3 C 0.1409(3) 1.0743(3) 0.5952(3) 0.0616(9) Uani 1 1 d . . . . .
H3 H 0.071915 1.125010 0.541771 0.074 Uiso 1 1 calc R U . . .
C4 C 0.1978(4) 1.1168(3) 0.6728(3) 0.0670(9) Uani 1 1 d . . . . .
H4 H 0.167184 1.196054 0.672154 0.080 Uiso 1 1 calc R U . . .
C5 C 0.2997(4) 1.0417(3) 0.7510(3) 0.0664(9) Uani 1 1 d . . . . .
H5 H 0.337559 1.070403 0.803599 0.080 Uiso 1 1 calc R U . . .
C6 C 0.3470(3) 0.9238(3) 0.7526(2) 0.0554(8) Uani 1 1 d . . . . .
H6 H 0.416173 0.873646 0.806229 0.066 Uiso 1 1 calc R U . . .
C7 C 0.3475(3) 0.7511(2) 0.6719(2) 0.0413(7) Uani 1 1 d . . . . .
C8 C 0.2212(3) 0.7005(2) 0.6438(2) 0.0405(7) Uani 1 1 d . . . . .
C9 C 0.2007(3) 0.6795(2) 0.5434(2) 0.0501(7) Uani 1 1 d . . . . .
H9 H 0.265684 0.696141 0.489122 0.060 Uiso 1 1 calc R U . . .
C10 C 0.0840(4) 0.6338(3) 0.5231(3) 0.0644(9) Uani 1 1 d . . . . .
H10 H 0.072252 0.618379 0.455722 0.077 Uiso 1 1 calc R U . . .
C11 C -0.0141(4) 0.6113(3) 0.6013(4) 0.0720(10) Uani 1 1 d . . . . .
H11 H -0.092731 0.581202 0.586923 0.086 Uiso 1 1 calc R U . . .
C12 C 0.0037(3) 0.6331(3) 0.7011(3) 0.0711(10) Uani 1 1 d . . . . .
H12 H -0.063166 0.618076 0.754274 0.085 Uiso 1 1 calc R U . . .
C13 C 0.1208(3) 0.6772(2) 0.7225(3) 0.0561(8) Uani 1 1 d . . . . .
H13 H 0.132533 0.691404 0.790361 0.067 Uiso 1 1 calc R U . . .
C14 C 0.4696(3) 0.7457(2) 0.5912(2) 0.0445(7) Uani 1 1 d . . . . .
C15 C 0.5798(3) 0.8213(3) 0.5814(3) 0.0633(9) Uani 1 1 d . . . . .
H15A H 0.565972 0.880344 0.622346 0.076 Uiso 1 1 calc R U . . .
H15B H 0.680336 0.784630 0.574731 0.076 Uiso 1 1 calc R U . . .
C16 C 0.4756(3) 0.8405(3) 0.4882(3) 0.0608(9) Uani 1 1 d . . . . .
H16A H 0.512564 0.815852 0.424414 0.073 Uiso 1 1 calc R U . . .
H16B H 0.398254 0.911521 0.472006 0.073 Uiso 1 1 calc R U . . .
O4 O 0.2792(2) 0.70129(16) 0.28795(14) 0.0524(5) Uani 1 1 d . . . . .
H4A H 0.311394 0.629562 0.300535 0.079 Uiso 1 1 calc R U . . .
O5 O 0.2512(3) 0.5363(2) 0.1781(2) 0.0728(7) Uani 1 1 d . . . . .
O6 O 0.0914(3) 0.5975(2) 0.0437(2) 0.0926(8) Uani 1 1 d . . . . .
N2 N 0.1718(3) 0.6161(2) 0.1094(2) 0.0600(7) Uani 1 1 d . . . . .
C17 C 0.2778(3) 0.8894(2) 0.1681(2) 0.0396(7) Uani 1 1 d . . . . .
C18 C 0.2038(3) 0.9369(2) 0.2471(2) 0.0496(7) Uani 1 1 d . . . . .
H18 H 0.165897 0.888341 0.304979 0.059 Uiso 1 1 calc R U . . .
C19 C 0.1865(3) 1.0564(3) 0.2396(3) 0.0589(8) Uani 1 1 d . . . . .
H19 H 0.136962 1.087588 0.292701 0.071 Uiso 1 1 calc R U . . .
C20 C 0.2415(3) 1.1293(3) 0.1550(3) 0.0588(8) Uani 1 1 d . . . . .
H20 H 0.229596 1.209423 0.150646 0.071 Uiso 1 1 calc R U . . .
C21 C 0.3145(3) 1.0830(3) 0.0765(3) 0.0557(8) Uani 1 1 d . . . . .
H21 H 0.351534 1.132087 0.018498 0.067 Uiso 1 1 calc R U . . .
C22 C 0.3330(3) 0.9642(2) 0.0836(2) 0.0468(7) Uani 1 1 d . . . . .
H22 H 0.383520 0.933679 0.030478 0.056 Uiso 1 1 calc R U . . .
C23 C 0.2949(3) 0.7573(2) 0.1750(2) 0.0390(7) Uani 1 1 d . . . . .
C24 C 0.4448(3) 0.7056(2) 0.1404(2) 0.0376(6) Uani 1 1 d . . . . .
C25 C 0.4680(3) 0.6767(2) 0.0416(2) 0.0421(7) Uani 1 1 d . . . . .
H25 H 0.389928 0.691322 -0.008635 0.051 Uiso 1 1 calc R U . . .
C26 C 0.6058(3) 0.6262(2) 0.0169(2) 0.0503(7) Uani 1 1 d . . . . .
H26 H 0.619704 0.607017 -0.049548 0.060 Uiso 1 1 calc R U . . .
C27 C 0.7218(3) 0.6044(2) 0.0897(3) 0.0531(8) Uani 1 1 d . . . . .
H27 H 0.813999 0.569247 0.073390 0.064 Uiso 1 1 calc R U . . .
C28 C 0.7018(3) 0.6347(2) 0.1872(3) 0.0559(8) Uani 1 1 d . . . . .
H28 H 0.780648 0.620678 0.236454 0.067 Uiso 1 1 calc R U . . .
C29 C 0.5648(3) 0.6857(2) 0.2118(2) 0.0468(7) Uani 1 1 d . . . . .
H29 H 0.552422 0.707122 0.277298 0.056 Uiso 1 1 calc R U . . .
C30 C 0.1712(3) 0.7419(2) 0.1049(2) 0.0456(7) Uani 1 1 d . . . . .
C31 C 0.0186(3) 0.8158(3) 0.0971(3) 0.0646(9) Uani 1 1 d . . . . .
H31A H -0.061094 0.776168 0.098522 0.078 Uiso 1 1 calc R U . . .
H31B H 0.001514 0.879558 0.132641 0.078 Uiso 1 1 calc R U . . .
C32 C 0.1057(3) 0.8290(3) -0.0005(3) 0.0617(9) Uani 1 1 d . . . . .
H32A H 0.141641 0.901049 -0.024886 0.074 Uiso 1 1 calc R U . . .
H32B H 0.079067 0.797716 -0.058986 0.074 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
O1 H1 0.8200 . ?
O1 C7 1.429(3) . ?
O2 N1 1.217(3) . ?
O3 N1 1.221(3) . ?
N1 C14 1.492(3) . ?
C1 C2 1.384(4) . ?
C1 C6 1.393(4) . ?
C1 C7 1.528(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.379(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.378(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.368(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.383(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.531(4) . ?
C7 C14 1.539(4) . ?
C8 C9 1.380(4) . ?
C8 C13 1.388(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.384(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.367(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.373(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.380(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.504(4) . ?
C14 C16 1.494(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.475(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
O4 H4A 0.8200 . ?
O4 C23 1.430(3) . ?
O5 N2 1.220(3) . ?
O6 N2 1.222(3) . ?
N2 C30 1.492(4) . ?
C17 C18 1.391(4) . ?
C17 C22 1.381(4) . ?
C17 C23 1.535(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.385(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.368(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.376(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.376(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.530(4) . ?
C23 C30 1.540(4) . ?
C24 C25 1.387(3) . ?
C24 C29 1.390(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.384(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.368(4) . ?
C27 H27 0.9300 . ?
C27 C28 1.375(4) . ?
C28 H28 0.9300 . ?
C28 C29 1.379(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.508(4) . ?
C30 C32 1.496(4) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C31 C32 1.473(4) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?

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
C7 O1 H1 109.5 . . ?
O2 N1 O3 123.1(3) . . ?
O2 N1 C14 118.1(3) . . ?
O3 N1 C14 118.7(3) . . ?
C2 C1 C6 118.3(3) . . ?
C2 C1 C7 121.1(2) . . ?
C6 C1 C7 120.6(2) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.2(3) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.9(3) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.7(3) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 H6 119.9 . . ?
C5 C6 C1 120.1(3) . . ?
C5 C6 H6 119.9 . . ?
O1 C7 C1 106.0(2) . . ?
O1 C7 C8 109.9(2) . . ?
O1 C7 C14 108.6(2) . . ?
C1 C7 C8 109.7(2) . . ?
C1 C7 C14 109.0(2) . . ?
C8 C7 C14 113.3(2) . . ?
C9 C8 C7 123.2(2) . . ?
C9 C8 C13 118.5(3) . . ?
C13 C8 C7 118.2(2) . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.4(3) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.4(3) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.9(3) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.0(3) . . ?
C13 C12 H12 120.0 . . ?
C8 C13 H13 119.6 . . ?
C12 C13 C8 120.7(3) . . ?
C12 C13 H13 119.6 . . ?
N1 C14 C7 115.0(2) . . ?
N1 C14 C15 111.0(2) . . ?
N1 C14 C16 113.4(2) . . ?
C15 C14 C7 122.0(2) . . ?
C16 C14 C7 124.7(2) . . ?
C16 C14 C15 58.91(19) . . ?
C14 C15 H15A 117.8 . . ?
C14 C15 H15B 117.8 . . ?
H15A C15 H15B 114.9 . . ?
C16 C15 C14 60.20(19) . . ?
C16 C15 H15A 117.8 . . ?
C16 C15 H15B 117.8 . . ?
C14 C16 H16A 117.7 . . ?
C14 C16 H16B 117.7 . . ?
C15 C16 C14 60.89(19) . . ?
C15 C16 H16A 117.7 . . ?
C15 C16 H16B 117.7 . . ?
H16A C16 H16B 114.8 . . ?
C23 O4 H4A 109.5 . . ?
O5 N2 O6 122.5(3) . . ?
O5 N2 C30 119.3(3) . . ?
O6 N2 C30 118.2(3) . . ?
C18 C17 C23 120.3(2) . . ?
C22 C17 C18 118.3(2) . . ?
C22 C17 C23 121.4(2) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.1(3) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 119.6 . . ?
C20 C19 C18 120.8(3) . . ?
C20 C19 H19 119.6 . . ?
C19 C20 H20 120.3 . . ?
C19 C20 C21 119.5(3) . . ?
C21 C20 H20 120.3 . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.2(3) . . ?
C22 C21 H21 119.9 . . ?
C17 C22 H22 119.4 . . ?
C21 C22 C17 121.2(3) . . ?
C21 C22 H22 119.4 . . ?
O4 C23 C17 105.23(19) . . ?
O4 C23 C24 110.1(2) . . ?
O4 C23 C30 108.9(2) . . ?
C17 C23 C30 109.4(2) . . ?
C24 C23 C17 110.9(2) . . ?
C24 C23 C30 112.1(2) . . ?
C25 C24 C23 123.7(2) . . ?
C25 C24 C29 117.9(2) . . ?
C29 C24 C23 118.4(2) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 C24 120.8(3) . . ?
C26 C25 H25 119.6 . . ?
C25 C26 H26 119.8 . . ?
C27 C26 C25 120.3(3) . . ?
C27 C26 H26 119.8 . . ?
C26 C27 H27 120.1 . . ?
C26 C27 C28 119.9(3) . . ?
C28 C27 H27 120.1 . . ?
C27 C28 H28 120.0 . . ?
C27 C28 C29 120.0(3) . . ?
C29 C28 H28 120.0 . . ?
C24 C29 H29 119.5 . . ?
C28 C29 C24 121.1(3) . . ?
C28 C29 H29 119.5 . . ?
N2 C30 C23 114.5(2) . . ?
N2 C30 C31 111.6(2) . . ?
N2 C30 C32 113.9(2) . . ?
C31 C30 C23 122.3(2) . . ?
C32 C30 C23 124.3(2) . . ?
C32 C30 C31 58.72(19) . . ?
C30 C31 H31A 117.7 . . ?
C30 C31 H31B 117.7 . . ?
H31A C31 H31B 114.9 . . ?
C32 C31 C30 60.23(19) . . ?
C32 C31 H31A 117.7 . . ?
C32 C31 H31B 117.7 . . ?
C30 C32 H32A 117.7 . . ?
C30 C32 H32B 117.7 . . ?
C31 C32 C30 61.04(19) . . ?
C31 C32 H32A 117.7 . . ?
C31 C32 H32B 117.7 . . ?
H32A C32 H32B 114.8 . . ?

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
O1 C7 C8 C9 -136.8(3) . . . . ?
O1 C7 C8 C13 44.7(3) . . . . ?
O1 C7 C14 N1 62.7(3) . . . . ?
O1 C7 C14 C15 -76.5(3) . . . . ?
O1 C7 C14 C16 -148.6(3) . . . . ?
O2 N1 C14 C7 -10.4(3) . . . . ?
O2 N1 C14 C15 133.2(3) . . . . ?
O2 N1 C14 C16 -162.7(3) . . . . ?
O3 N1 C14 C7 171.4(2) . . . . ?
O3 N1 C14 C15 -45.0(3) . . . . ?
O3 N1 C14 C16 19.1(4) . . . . ?
N1 C14 C15 C16 105.3(3) . . . . ?
N1 C14 C16 C15 -101.3(3) . . . . ?
C1 C2 C3 C4 -1.5(4) . . . . ?
C1 C7 C8 C9 107.0(3) . . . . ?
C1 C7 C8 C13 -71.5(3) . . . . ?
C1 C7 C14 N1 177.8(2) . . . . ?
C1 C7 C14 C15 38.6(3) . . . . ?
C1 C7 C14 C16 -33.5(3) . . . . ?
C2 C1 C6 C5 -1.3(4) . . . . ?
C2 C1 C7 O1 -158.7(2) . . . . ?
C2 C1 C7 C8 -40.1(3) . . . . ?
C2 C1 C7 C14 84.6(3) . . . . ?
C2 C3 C4 C5 0.2(5) . . . . ?
C3 C4 C5 C6 0.4(5) . . . . ?
C4 C5 C6 C1 0.1(5) . . . . ?
C6 C1 C2 C3 2.0(4) . . . . ?
C6 C1 C7 O1 22.8(3) . . . . ?
C6 C1 C7 C8 141.4(2) . . . . ?
C6 C1 C7 C14 -94.0(3) . . . . ?
C7 C1 C2 C3 -176.6(2) . . . . ?
C7 C1 C6 C5 177.3(3) . . . . ?
C7 C8 C9 C10 -179.8(2) . . . . ?
C7 C8 C13 C12 179.1(3) . . . . ?
C7 C14 C15 C16 -114.1(3) . . . . ?
C7 C14 C16 C15 109.6(3) . . . . ?
C8 C7 C14 N1 -59.7(3) . . . . ?
C8 C7 C14 C15 161.1(2) . . . . ?
C8 C7 C14 C16 89.1(3) . . . . ?
C8 C9 C10 C11 1.4(4) . . . . ?
C9 C8 C13 C12 0.5(4) . . . . ?
C9 C10 C11 C12 -0.5(5) . . . . ?
C10 C11 C12 C13 -0.3(5) . . . . ?
C11 C12 C13 C8 0.3(4) . . . . ?
C13 C8 C9 C10 -1.3(4) . . . . ?
C14 C7 C8 C9 -15.1(3) . . . . ?
C14 C7 C8 C13 166.4(2) . . . . ?
O4 C23 C24 C25 136.9(2) . . . . ?
O4 C23 C24 C29 -42.6(3) . . . . ?
O4 C23 C30 N2 -62.7(3) . . . . ?
O4 C23 C30 C31 77.4(3) . . . . ?
O4 C23 C30 C32 149.2(2) . . . . ?
O5 N2 C30 C23 11.3(4) . . . . ?
O5 N2 C30 C31 -133.0(3) . . . . ?
O5 N2 C30 C32 162.8(3) . . . . ?
O6 N2 C30 C23 -169.0(2) . . . . ?
O6 N2 C30 C31 46.7(3) . . . . ?
O6 N2 C30 C32 -17.5(4) . . . . ?
N2 C30 C31 C32 -105.6(3) . . . . ?
N2 C30 C32 C31 101.7(3) . . . . ?
C17 C18 C19 C20 0.0(4) . . . . ?
C17 C23 C24 C25 -107.0(3) . . . . ?
C17 C23 C24 C29 73.4(3) . . . . ?
C17 C23 C30 N2 -177.2(2) . . . . ?
C17 C23 C30 C31 -37.1(3) . . . . ?
C17 C23 C30 C32 34.7(3) . . . . ?
C18 C17 C22 C21 -0.6(4) . . . . ?
C18 C17 C23 O4 -23.0(3) . . . . ?
C18 C17 C23 C24 -142.0(2) . . . . ?
C18 C17 C23 C30 93.9(3) . . . . ?
C18 C19 C20 C21 0.1(5) . . . . ?
C19 C20 C21 C22 -0.5(4) . . . . ?
C20 C21 C22 C17 0.7(4) . . . . ?
C22 C17 C18 C19 0.2(4) . . . . ?
C22 C17 C23 O4 157.9(2) . . . . ?
C22 C17 C23 C24 38.8(3) . . . . ?
C22 C17 C23 C30 -85.3(3) . . . . ?
C23 C17 C18 C19 -178.9(2) . . . . ?
C23 C17 C22 C21 178.6(2) . . . . ?
C23 C24 C25 C26 -177.7(2) . . . . ?
C23 C24 C29 C28 177.2(2) . . . . ?
C23 C30 C31 C32 113.4(3) . . . . ?
C23 C30 C32 C31 -110.0(3) . . . . ?
C24 C23 C30 N2 59.4(3) . . . . ?
C24 C23 C30 C31 -160.5(2) . . . . ?
C24 C23 C30 C32 -88.7(3) . . . . ?
C24 C25 C26 C27 -0.2(4) . . . . ?
C25 C24 C29 C28 -2.4(4) . . . . ?
C25 C26 C27 C28 -1.1(4) . . . . ?
C26 C27 C28 C29 0.7(4) . . . . ?
C27 C28 C29 C24 1.1(4) . . . . ?
C29 C24 C25 C26 1.9(4) . . . . ?
C30 C23 C24 C25 15.6(3) . . . . ?
C30 C23 C24 C29 -164.0(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
