# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_map343n_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 1825830'
loop_
_audit_author_name
_audit_author_address
'Joerg-M. Neudoerfl'
;Department of Chemistry Organic Cemistry University of Cologne
Germany
;
_audit_update_record             
;
2019-06-14 deposited with the CCDC.	2019-07-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H13 N O3, C9 H11 N O'
_chemical_formula_sum            'C20 H24 N2 O4'
_chemical_formula_weight         356.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6578(3)
_cell_length_b                   10.0035(4)
_cell_length_c                   11.6371(4)
_cell_angle_alpha                78.7640(10)
_cell_angle_beta                 75.9780(10)
_cell_angle_gamma                67.1630(10)
_cell_volume                     895.44(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    13387
_cell_measurement_theta_min      3.940
_cell_measurement_theta_max      72.152

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_F_000             380
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.754
_shelx_estimated_absorpt_T_min   0.864
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6285
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro focus'
_diffrn_measurement_device_type  'Bruker D8'
_diffrn_measurement_method       'phi / omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13387
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.940
_diffrn_reflns_theta_max         72.152
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             3476
_reflns_number_gt                3173
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX 3'
_computing_cell_refinement       'Bruker APEX 3'
_computing_data_reduction        'Bruker APEX 3'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_computing_structure_refinement  
;
SHELXL-2014/7 (Sheldrick, 2014)
SHELXLE (C. B. Huebschle 2016)'
;
_computing_molecular_graphics    'SCHAKAL99 (E. Keller 1999)'
_computing_publication_material  'PLATON (A. L. Spek 1980-2015)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0529P)²+0.6405P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3476
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1273
_refine_ls_wR_factor_gt          0.1248
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O001 O 0.73267(14) 0.55134(13) 0.41944(9) 0.0185(3) Uani 1 1 d . . . . .
H001 H 0.642(3) 0.533(3) 0.464(2) 0.049(7) Uiso 1 1 d . . . . .
O002 O 0.52884(13) 0.42841(12) 0.38059(9) 0.0177(3) Uani 1 1 d . . . . .
O003 O 0.64495(14) 0.42176(12) 0.18613(9) 0.0171(3) Uani 1 1 d . . . . .
H003 H 0.569(3) 0.380(2) 0.1875(4) 0.026 Uiso 1 1 calc R U . . .
O004 O 0.43569(14) 0.29330(13) 0.17955(10) 0.0207(3) Uani 1 1 d . . . . .
N005 N 1.39454(16) 0.75473(15) 0.21571(11) 0.0168(3) Uani 1 1 d . . . . .
N006 N -0.18057(17) 0.05559(15) 0.27216(12) 0.0190(3) Uani 1 1 d . . . . .
C007 C 0.99909(18) 0.60356(16) 0.21827(13) 0.0135(3) Uani 1 1 d . . . . .
C008 C 0.19484(18) 0.22533(16) 0.26519(14) 0.0145(3) Uani 1 1 d . . . . .
C009 C 1.02175(19) 0.64018(17) 0.32201(13) 0.0160(3) Uani 1 1 d . . . . .
H009 H 0.9473 0.6295 0.3951 0.019 Uiso 1 1 calc R U . . .
C00A C 1.26359(18) 0.70876(16) 0.21516(13) 0.0130(3) Uani 1 1 d . . . . .
C00B C 1.24255(19) 0.67153(16) 0.11028(13) 0.0149(3) Uani 1 1 d . . . . .
H00B H 1.3172 0.6815 0.0372 0.018 Uiso 1 1 calc R U . . .
C00C C -0.05762(19) 0.10835(16) 0.27062(14) 0.0151(3) Uani 1 1 d . . . . .
C00D C 0.86890(18) 0.54626(16) 0.21585(13) 0.0137(3) Uani 1 1 d . . . . .
H00D H 0.863(2) 0.5177(19) 0.1369(16) 0.012(4) Uiso 1 1 d . . . . .
C00E C 0.74970(19) 0.52181(16) 0.30649(13) 0.0143(3) Uani 1 1 d . . . . .
C00F C 0.63040(19) 0.45432(16) 0.29395(13) 0.0150(3) Uani 1 1 d . . . . .
C00G C 1.11367(19) 0.62053(16) 0.11351(13) 0.0144(3) Uani 1 1 d . . . . .
H00G H 1.1026 0.5961 0.0418 0.017 Uiso 1 1 calc R U . . .
C00H C -0.04587(19) 0.15746(17) 0.37310(13) 0.0157(3) Uani 1 1 d . . . . .
H00H H -0.1228 0.1500 0.4456 0.019 Uiso 1 1 calc R U . . .
C00I C 0.07576(19) 0.21596(17) 0.36920(14) 0.0164(3) Uani 1 1 d . . . . .
H00I H 0.0789 0.2507 0.4386 0.020 Uiso 1 1 calc R U . . .
C00J C 0.1856(2) 0.17494(17) 0.16367(14) 0.0186(3) Uani 1 1 d . . . . .
H00J H 0.2652 0.1802 0.0922 0.022 Uiso 1 1 calc R U . . .
C00K C 1.1492(2) 0.69131(17) 0.32078(13) 0.0167(3) Uani 1 1 d . . . . .
H00K H 1.1600 0.7152 0.3928 0.020 Uiso 1 1 calc R U . . .
C00L C 1.4957(2) 0.78988(18) 0.10376(14) 0.0179(3) Uani 1 1 d . . . . .
H00A H 1.5443 0.7060 0.0578 0.027 Uiso 1 1 calc R U . . .
H00C H 1.5880 0.8133 0.1195 0.027 Uiso 1 1 calc R U . . .
H00E H 1.4233 0.8741 0.0583 0.027 Uiso 1 1 calc R U . . .
C00M C 0.0637(2) 0.11809(18) 0.16556(14) 0.0184(3) Uani 1 1 d . . . . .
H00M H 0.0605 0.0847 0.0954 0.022 Uiso 1 1 calc R U . . .
C00N C 0.32034(19) 0.28834(16) 0.26459(14) 0.0166(3) Uani 1 1 d . . . . .
H00N H 0.318(2) 0.3260(19) 0.3405(16) 0.011(4) Uiso 1 1 d . . . . .
C00O C 1.3922(2) 0.81684(17) 0.31933(14) 0.0181(3) Uani 1 1 d . . . . .
H00F H 1.4942 0.8420 0.3069 0.027 Uiso 1 1 calc R U . . .
H00L H 1.3906 0.7454 0.3900 0.027 Uiso 1 1 calc R U . . .
H00O H 1.2902 0.9050 0.3310 0.027 Uiso 1 1 calc R U . . .
C00P C -0.1917(2) 0.00674(19) 0.16543(15) 0.0220(4) Uani 1 1 d . . . . .
H00P H -0.1974 0.0849 0.0993 0.033 Uiso 1 1 calc R U . . .
H00Q H -0.2945 -0.0179 0.1803 0.033 Uiso 1 1 calc R U . . .
H00R H -0.0908 -0.0797 0.1449 0.033 Uiso 1 1 calc R U . . .
C00Q C -0.3000(2) 0.0409(2) 0.38102(15) 0.0237(4) Uani 1 1 d . . . . .
H00S H -0.3768 -0.0016 0.3657 0.036 Uiso 1 1 calc R U . . .
H00T H -0.3668 0.1372 0.4081 0.036 Uiso 1 1 calc R U . . .
H00U H -0.2371 -0.0230 0.4427 0.036 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
O001 C00E 1.3640(18) . ?
O001 H001 0.89(3) . ?
O002 C00F 1.2257(18) . ?
O003 C00F 1.3218(19) . ?
O003 H003 0.90(2) . ?
O004 C00N 1.2327(19) . ?
N005 C00A 1.3807(18) . ?
N005 C00L 1.4476(18) . ?
N005 C00O 1.453(2) . ?
N006 C00C 1.355(2) . ?
N006 C00Q 1.452(2) . ?
N006 C00P 1.457(2) . ?
C007 C00G 1.401(2) . ?
C007 C009 1.405(2) . ?
C007 C00D 1.457(2) . ?
C008 C00I 1.401(2) . ?
C008 C00J 1.402(2) . ?
C008 C00N 1.451(2) . ?
C009 C00K 1.381(2) . ?
C009 H009 0.9500 . ?
C00A C00K 1.408(2) . ?
C00A C00B 1.414(2) . ?
C00B C00G 1.386(2) . ?
C00B H00B 0.9500 . ?
C00C C00H 1.414(2) . ?
C00C C00M 1.421(2) . ?
C00D C00E 1.344(2) . ?
C00D H00D 1.033(18) . ?
C00E C00F 1.482(2) . ?
C00G H00G 0.9500 . ?
C00H C00I 1.378(2) . ?
C00H H00H 0.9500 . ?
C00I H00I 0.9500 . ?
C00J C00M 1.374(2) . ?
C00J H00J 0.9500 . ?
C00K H00K 0.9500 . ?
C00L H00A 0.9800 . ?
C00L H00C 0.9800 . ?
C00L H00E 0.9800 . ?
C00M H00M 0.9500 . ?
C00N H00N 1.020(18) . ?
C00O H00F 0.9800 . ?
C00O H00L 0.9800 . ?
C00O H00O 0.9800 . ?
C00P H00P 0.9800 . ?
C00P H00Q 0.9800 . ?
C00P H00R 0.9800 . ?
C00Q H00S 0.9800 . ?
C00Q H00T 0.9800 . ?
C00Q H00U 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
C00E O001 H001 108.3(17) . . ?
C00F O003 H003 109.5 . . ?
C00A N005 C00L 119.51(13) . . ?
C00A N005 C00O 119.26(12) . . ?
C00L N005 C00O 117.61(12) . . ?
C00C N006 C00Q 120.98(14) . . ?
C00C N006 C00P 120.66(13) . . ?
C00Q N006 C00P 118.32(13) . . ?
C00G C007 C009 116.42(13) . . ?
C00G C007 C00D 119.80(14) . . ?
C009 C007 C00D 123.75(13) . . ?
C00I C008 C00J 117.98(14) . . ?
C00I C008 C00N 119.81(14) . . ?
C00J C008 C00N 122.20(14) . . ?
C00K C009 C007 121.86(14) . . ?
C00K C009 H009 119.1 . . ?
C007 C009 H009 119.1 . . ?
N005 C00A C00K 121.05(13) . . ?
N005 C00A C00B 121.76(13) . . ?
C00K C00A C00B 117.15(13) . . ?
C00G C00B C00A 120.40(13) . . ?
C00G C00B H00B 119.8 . . ?
C00A C00B H00B 119.8 . . ?
N006 C00C C00H 121.40(14) . . ?
N006 C00C C00M 121.33(14) . . ?
C00H C00C C00M 117.26(14) . . ?
C00E C00D C007 128.28(14) . . ?
C00E C00D H00D 112.1(10) . . ?
C007 C00D H00D 119.6(10) . . ?
C00D C00E O001 122.84(13) . . ?
C00D C00E C00F 123.06(14) . . ?
O001 C00E C00F 114.05(13) . . ?
O002 C00F O003 123.56(14) . . ?
O002 C00F C00E 120.57(14) . . ?
O003 C00F C00E 115.85(13) . . ?
C00B C00G C007 122.67(14) . . ?
C00B C00G H00G 118.7 . . ?
C007 C00G H00G 118.7 . . ?
C00I C00H C00C 120.85(14) . . ?
C00I C00H H00H 119.6 . . ?
C00C C00H H00H 119.6 . . ?
C00H C00I C008 121.51(14) . . ?
C00H C00I H00I 119.2 . . ?
C008 C00I H00I 119.2 . . ?
C00M C00J C008 121.26(14) . . ?
C00M C00J H00J 119.4 . . ?
C008 C00J H00J 119.4 . . ?
C009 C00K C00A 121.49(14) . . ?
C009 C00K H00K 119.3 . . ?
C00A C00K H00K 119.3 . . ?
N005 C00L H00A 109.5 . . ?
N005 C00L H00C 109.5 . . ?
H00A C00L H00C 109.5 . . ?
N005 C00L H00E 109.5 . . ?
H00A C00L H00E 109.5 . . ?
H00C C00L H00E 109.5 . . ?
C00J C00M C00C 121.11(15) . . ?
C00J C00M H00M 119.4 . . ?
C00C C00M H00M 119.4 . . ?
O004 C00N C008 124.19(15) . . ?
O004 C00N H00N 117.2(10) . . ?
C008 C00N H00N 118.5(10) . . ?
N005 C00O H00F 109.5 . . ?
N005 C00O H00L 109.5 . . ?
H00F C00O H00L 109.5 . . ?
N005 C00O H00O 109.5 . . ?
H00F C00O H00O 109.5 . . ?
H00L C00O H00O 109.5 . . ?
N006 C00P H00P 109.5 . . ?
N006 C00P H00Q 109.5 . . ?
H00P C00P H00Q 109.5 . . ?
N006 C00P H00R 109.5 . . ?
H00P C00P H00R 109.5 . . ?
H00Q C00P H00R 109.5 . . ?
N006 C00Q H00S 109.5 . . ?
N006 C00Q H00T 109.5 . . ?
H00S C00Q H00T 109.5 . . ?
N006 C00Q H00U 109.5 . . ?
H00S C00Q H00U 109.5 . . ?
H00T C00Q H00U 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
C00G C007 C009 C00K 0.5(2) . . . . ?
C00D C007 C009 C00K 178.60(14) . . . . ?
C00L N005 C00A C00K -171.93(14) . . . . ?
C00O N005 C00A C00K -13.9(2) . . . . ?
C00L N005 C00A C00B 10.7(2) . . . . ?
C00O N005 C00A C00B 168.75(14) . . . . ?
N005 C00A C00B C00G 177.58(14) . . . . ?
C00K C00A C00B C00G 0.1(2) . . . . ?
C00Q N006 C00C C00H -3.0(2) . . . . ?
C00P N006 C00C C00H 179.42(14) . . . . ?
C00Q N006 C00C C00M 177.66(14) . . . . ?
C00P N006 C00C C00M 0.1(2) . . . . ?
C00G C007 C00D C00E 179.60(14) . . . . ?
C009 C007 C00D C00E 1.6(3) . . . . ?
C007 C00D C00E O001 1.0(2) . . . . ?
C007 C00D C00E C00F -176.14(14) . . . . ?
C00D C00E C00F O002 176.77(14) . . . . ?
O001 C00E C00F O002 -0.6(2) . . . . ?
C00D C00E C00F O003 -1.5(2) . . . . ?
O001 C00E C00F O003 -178.89(12) . . . . ?
C00A C00B C00G C007 0.1(2) . . . . ?
C009 C007 C00G C00B -0.5(2) . . . . ?
C00D C007 C00G C00B -178.63(14) . . . . ?
N006 C00C C00H C00I -177.55(14) . . . . ?
C00M C00C C00H C00I 1.8(2) . . . . ?
C00C C00H C00I C008 -1.8(2) . . . . ?
C00J C008 C00I C00H 0.8(2) . . . . ?
C00N C008 C00I C00H 179.69(14) . . . . ?
C00I C008 C00J C00M 0.1(2) . . . . ?
C00N C008 C00J C00M -178.78(14) . . . . ?
C007 C009 C00K C00A -0.3(2) . . . . ?
N005 C00A C00K C009 -177.54(14) . . . . ?
C00B C00A C00K C009 -0.1(2) . . . . ?
C008 C00J C00M C00C 0.0(2) . . . . ?
N006 C00C C00M C00J 178.42(15) . . . . ?
C00H C00C C00M C00J -0.9(2) . . . . ?
C00I C008 C00N O004 175.64(14) . . . . ?
C00J C008 C00N O004 -5.6(2) . . . . ?

_refine_diff_density_max         0.292
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_tto_ma_acn1_0m_num1
_database_code_depnum_ccdc_archive 'CCDC 1911879'
loop_
_audit_author_name
_audit_author_address
'Joerg-M. Neudoerfl'
;Department of Chemistry Organic Cemistry University of Cologne
Germany
;
_audit_update_record             
;
2019-06-14 deposited with the CCDC.	2019-07-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C12 H16 N O3), C2 H3 N, 2(I), H2 O'
_chemical_formula_sum            'C26 H37 I2 N3 O7'
_chemical_formula_weight         757.38

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'
I I -0.3257 6.8362 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.2439(3)
_cell_length_b                   11.9323(3)
_cell_length_c                   14.7966(4)
_cell_angle_alpha                72.9180(10)
_cell_angle_beta                 83.3110(10)
_cell_angle_gamma                65.7470(10)
_cell_volume                     1576.24(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9122
_cell_measurement_theta_min      3.12
_cell_measurement_theta_max      72.10

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.265
_exptl_crystal_size_mid          0.242
_exptl_crystal_size_min          0.096
_exptl_absorpt_coefficient_mu    16.039
_shelx_estimated_absorpt_T_min   0.101
_shelx_estimated_absorpt_T_max   0.308
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.0170
_exptl_absorpt_correction_T_max  0.1726
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   
;
numerical Absorption correction after face indexing with APEXIII)
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro focus'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'phi / omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40714
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.124
_diffrn_reflns_theta_max         72.171
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             6163
_reflns_number_gt                5858
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX 3'
_computing_cell_refinement       'Bruker APEX 3'
_computing_data_reduction        'Bruker APEX 3'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_computing_structure_refinement  
;
SHELXL-2014/7 (Sheldrick, 2014)
SHELXLE (C. B. Huebschle 2016)'
;
_computing_molecular_graphics    'SCHAKAL99 (E. Keller 1999)'
_computing_publication_material  'PLATON (A. L. Spek 1980-2015)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0589P)²+3.5326P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6163
_refine_ls_number_parameters     374
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.0994
_refine_ls_wR_factor_gt          0.0966
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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
I1 I 0.19208(3) 0.41720(2) 0.85724(2) 0.02668(9) Uani 1 1 d . . . . .
I2 I 0.66061(2) 0.19656(2) 0.05006(2) 0.02304(9) Uani 1 1 d . . . . .
O1 O 0.3648(3) 0.3672(2) 0.57356(18) 0.0254(5) Uani 1 1 d . . . . .
O2 O 0.2026(3) 0.5390(3) 0.61576(19) 0.0308(6) Uani 1 1 d D . . . .
H2X H 0.210(7) 0.483(5) 0.666(3) 0.063(19) Uiso 1 1 d D . . . .
O3 O 0.4042(3) 0.5163(3) 0.40460(18) 0.0247(5) Uani 1 1 d . . . . .
H3X H 0.439(5) 0.446(5) 0.427(3) 0.025(12) Uiso 1 1 d . . . . .
O4 O 0.5805(3) 0.2743(2) 0.41090(18) 0.0253(5) Uani 1 1 d . . . . .
O5 O 0.7659(3) 0.1178(3) 0.3680(2) 0.0341(7) Uani 1 1 d . . . . .
H5X H 0.767(7) 0.173(7) 0.328(5) 0.06(2) Uiso 1 1 d . . . . .
O6 O 0.5361(3) 0.1122(3) 0.56756(18) 0.0241(5) Uani 1 1 d . . . . .
H6X H 0.506(5) 0.185(5) 0.549(3) 0.023(11) Uiso 1 1 d . . . . .
N1 N 0.1955(3) 1.1005(3) 0.1064(2) 0.0197(6) Uani 1 1 d . . . . .
N2 N 0.7103(3) -0.4959(3) 0.8179(2) 0.0178(6) Uani 1 1 d . . . . .
C1 C 0.2945(4) 0.4819(3) 0.5565(2) 0.0211(7) Uani 1 1 d . . . . .
C2 C 0.3071(4) 0.5714(3) 0.4649(2) 0.0198(7) Uani 1 1 d . . . . .
C3 C 0.2258(4) 0.6978(3) 0.4439(3) 0.0222(7) Uani 1 1 d . . . . .
H3 H 0.1602 0.7265 0.4913 0.027 Uiso 1 1 calc R U . . .
C4 C 0.2262(4) 0.7960(3) 0.3576(2) 0.0199(7) Uani 1 1 d . . . . .
C5 C 0.1098(4) 0.9131(4) 0.3409(3) 0.0305(8) Uani 1 1 d . . . . .
H5 H 0.0347 0.9265 0.3859 0.037 Uiso 1 1 calc R U . . .
C6 C 0.1013(4) 1.0101(4) 0.2603(3) 0.0307(9) Uani 1 1 d . . . . .
H6 H 0.0201 1.0889 0.2501 0.037 Uiso 1 1 calc R U . . .
C7 C 0.2090(4) 0.9939(3) 0.1948(2) 0.0191(7) Uani 1 1 d . . . . .
C8 C 0.3273(4) 0.8790(3) 0.2090(2) 0.0207(7) Uani 1 1 d . . . . .
H8 H 0.4018 0.8672 0.1636 0.025 Uiso 1 1 calc R U . . .
C9 C 0.3362(4) 0.7807(3) 0.2905(2) 0.0201(7) Uani 1 1 d . . . . .
H9 H 0.4180 0.7023 0.3007 0.024 Uiso 1 1 calc R U . . .
C10 C 0.3366(4) 1.0842(4) 0.0575(3) 0.0318(9) Uani 1 1 d . . . . .
H10A H 0.3244 1.1595 0.0041 0.048 Uiso 1 1 calc R U . . .
H10B H 0.3710 1.0080 0.0343 0.048 Uiso 1 1 calc R U . . .
H10C H 0.4065 1.0745 0.1021 0.048 Uiso 1 1 calc R U . . .
C11 C 0.0923(4) 1.1057(4) 0.0383(3) 0.0248(7) Uani 1 1 d . . . . .
H11A H 0.0824 1.1760 -0.0187 0.037 Uiso 1 1 calc R U . . .
H11B H -0.0014 1.1196 0.0685 0.037 Uiso 1 1 calc R U . . .
H11C H 0.1290 1.0249 0.0211 0.037 Uiso 1 1 calc R U . . .
C12 C 0.1368(5) 1.2279(3) 0.1288(3) 0.0276(8) Uani 1 1 d . . . . .
H12A H 0.1348 1.2951 0.0712 0.041 Uiso 1 1 calc R U . . .
H12B H 0.1980 1.2253 0.1763 0.041 Uiso 1 1 calc R U . . .
H12C H 0.0394 1.2459 0.1536 0.041 Uiso 1 1 calc R U . . .
C13 C 0.6596(4) 0.1627(3) 0.4246(2) 0.0205(7) Uani 1 1 d . . . . .
C14 C 0.6422(4) 0.0637(3) 0.5093(2) 0.0212(7) Uani 1 1 d . . . . .
C15 C 0.7236(4) -0.0610(3) 0.5230(3) 0.0225(7) Uani 1 1 d . . . . .
H15 H 0.7942 -0.0823 0.4762 0.027 Uiso 1 1 calc R U . . .
C16 C 0.7186(4) -0.1684(3) 0.5998(2) 0.0207(7) Uani 1 1 d . . . . .
C17 C 0.6161(4) -0.1565(3) 0.6725(2) 0.0216(7) Uani 1 1 d . . . . .
H17 H 0.5469 -0.0743 0.6739 0.026 Uiso 1 1 calc R U . . .
C18 C 0.6151(4) -0.2633(3) 0.7421(2) 0.0207(7) Uani 1 1 d . . . . .
H18 H 0.5450 -0.2541 0.7905 0.025 Uiso 1 1 calc R U . . .
C19 C 0.7164(4) -0.3837(3) 0.7409(2) 0.0188(6) Uani 1 1 d . . . . .
C20 C 0.8196(4) -0.3991(3) 0.6704(3) 0.0246(7) Uani 1 1 d . . . . .
H20 H 0.8897 -0.4814 0.6700 0.030 Uiso 1 1 calc R U . . .
C21 C 0.8177(4) -0.2911(4) 0.6006(3) 0.0261(8) Uani 1 1 d . . . . .
H21 H 0.8865 -0.3012 0.5515 0.031 Uiso 1 1 calc R U . . .
C22 C 0.8187(4) -0.6210(3) 0.8044(3) 0.0220(7) Uani 1 1 d . . . . .
H22A H 0.8029 -0.6292 0.7430 0.033 Uiso 1 1 calc R U . . .
H22B H 0.8086 -0.6915 0.8549 0.033 Uiso 1 1 calc R U . . .
H22C H 0.9154 -0.6239 0.8066 0.033 Uiso 1 1 calc R U . . .
C23 C 0.7411(4) -0.4869(3) 0.9128(2) 0.0218(7) Uani 1 1 d . . . . .
H23A H 0.8361 -0.4851 0.9116 0.033 Uiso 1 1 calc R U . . .
H23B H 0.7384 -0.5611 0.9627 0.033 Uiso 1 1 calc R U . . .
H23C H 0.6686 -0.4085 0.9255 0.033 Uiso 1 1 calc R U . . .
C24 C 0.5635(4) -0.4987(3) 0.8206(3) 0.0224(7) Uani 1 1 d . . . . .
H24A H 0.5391 -0.4963 0.7577 0.034 Uiso 1 1 calc R U . . .
H24B H 0.4924 -0.4244 0.8394 0.034 Uiso 1 1 calc R U . . .
H24C H 0.5638 -0.5772 0.8663 0.034 Uiso 1 1 calc R U . . .
O7 O 0.7972(3) 0.2786(3) 0.2133(2) 0.0280(6) Uani 1 1 d . . . . .
H7X H 0.784(6) 0.353(6) 0.202(4) 0.043(15) Uiso 1 1 d . . . . .
H7Y H 0.766(6) 0.272(5) 0.167(4) 0.038(14) Uiso 1 1 d . . . . .
N3 N 0.0630(4) 0.3018(4) 0.6383(3) 0.0446(9) Uani 1 1 d . . . . .
C25 C 0.2857(6) 0.1298(5) 0.7379(4) 0.0523(14) Uani 1 1 d . . . . .
H25A H 0.2717 0.0500 0.7642 0.078 Uiso 1 1 calc R U . . .
H25B H 0.2987 0.1603 0.7895 0.078 Uiso 1 1 calc R U . . .
H25C H 0.3708 0.1146 0.6976 0.078 Uiso 1 1 calc R U . . .
C26 C 0.1614(5) 0.2250(4) 0.6821(3) 0.0363(10) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.218(4) . ?
O2 C1 1.323(5) . ?
O2 H2X 0.83(2) . ?
O3 C2 1.349(4) . ?
O3 H3X 0.75(5) . ?
O4 C13 1.210(4) . ?
O5 C13 1.321(4) . ?
O5 H5X 0.75(7) . ?
O6 C14 1.348(4) . ?
O6 H6X 0.77(5) . ?
N1 C10 1.504(4) . ?
N1 C7 1.506(4) . ?
N1 C12 1.510(5) . ?
N1 C11 1.514(5) . ?
N2 C19 1.500(4) . ?
N2 C22 1.504(4) . ?
N2 C24 1.513(4) . ?
N2 C23 1.518(4) . ?
C1 C2 1.489(5) . ?
C2 C3 1.349(5) . ?
C3 C4 1.458(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(5) . ?
C4 C9 1.402(5) . ?
C5 C6 1.379(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.371(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.385(5) . ?
C8 C9 1.394(5) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.500(5) . ?
C14 C15 1.339(5) . ?
C15 C16 1.456(5) . ?
C15 H15 0.9500 . ?
C16 C21 1.395(5) . ?
C16 C17 1.409(5) . ?
C17 C18 1.386(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.388(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.392(5) . ?
C20 C21 1.389(5) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
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 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
O7 H7X 0.81(6) . ?
O7 H7Y 0.83(6) . ?
N3 C26 1.149(6) . ?
C25 C26 1.448(7) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 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
C1 O2 H2X 106(5) . . ?
C2 O3 H3X 109(4) . . ?
C13 O5 H5X 108(5) . . ?
C14 O6 H6X 108(3) . . ?
C10 N1 C7 112.4(3) . . ?
C10 N1 C12 107.7(3) . . ?
C7 N1 C12 110.8(3) . . ?
C10 N1 C11 108.6(3) . . ?
C7 N1 C11 109.6(3) . . ?
C12 N1 C11 107.7(3) . . ?
C19 N2 C22 112.4(3) . . ?
C19 N2 C24 110.2(3) . . ?
C22 N2 C24 107.9(3) . . ?
C19 N2 C23 109.9(3) . . ?
C22 N2 C23 107.4(3) . . ?
C24 N2 C23 109.0(3) . . ?
O1 C1 O2 124.6(3) . . ?
O1 C1 C2 121.7(3) . . ?
O2 C1 C2 113.7(3) . . ?
C3 C2 O3 122.9(3) . . ?
C3 C2 C1 122.1(3) . . ?
O3 C2 C1 115.0(3) . . ?
C2 C3 C4 128.1(3) . . ?
C2 C3 H3 116.0 . . ?
C4 C3 H3 116.0 . . ?
C5 C4 C9 117.7(3) . . ?
C5 C4 C3 117.8(3) . . ?
C9 C4 C3 124.5(3) . . ?
C6 C5 C4 121.3(3) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C7 C6 C5 120.6(3) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 120.0(3) . . ?
C6 C7 N1 119.5(3) . . ?
C8 C7 N1 120.5(3) . . ?
C7 C8 C9 119.5(3) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C8 C9 C4 120.9(3) . . ?
C8 C9 H9 119.5 . . ?
C4 C9 H9 119.5 . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O4 C13 O5 124.0(3) . . ?
O4 C13 C14 121.2(3) . . ?
O5 C13 C14 114.8(3) . . ?
C15 C14 O6 124.2(3) . . ?
C15 C14 C13 122.1(3) . . ?
O6 C14 C13 113.7(3) . . ?
C14 C15 C16 128.8(3) . . ?
C14 C15 H15 115.6 . . ?
C16 C15 H15 115.6 . . ?
C21 C16 C17 117.4(3) . . ?
C21 C16 C15 118.7(3) . . ?
C17 C16 C15 123.8(3) . . ?
C18 C17 C16 120.8(3) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C19 120.0(3) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C20 120.8(3) . . ?
C18 C19 N2 117.8(3) . . ?
C20 C19 N2 121.4(3) . . ?
C21 C20 C19 118.3(3) . . ?
C21 C20 H20 120.8 . . ?
C19 C20 H20 120.8 . . ?
C20 C21 C16 122.6(3) . . ?
C20 C21 H21 118.7 . . ?
C16 C21 H21 118.7 . . ?
N2 C22 H22A 109.5 . . ?
N2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N2 C23 H23A 109.5 . . ?
N2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N2 C24 H24A 109.5 . . ?
N2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
H7X O7 H7Y 106(5) . . ?
C26 C25 H25A 109.5 . . ?
C26 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C26 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N3 C26 C25 179.1(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 C1 C2 C3 177.4(3) . . . . ?
O2 C1 C2 C3 -3.2(5) . . . . ?
O1 C1 C2 O3 -2.0(5) . . . . ?
O2 C1 C2 O3 177.5(3) . . . . ?
O3 C2 C3 C4 -0.5(6) . . . . ?
C1 C2 C3 C4 -179.8(3) . . . . ?
C2 C3 C4 C5 163.5(4) . . . . ?
C2 C3 C4 C9 -16.9(6) . . . . ?
C9 C4 C5 C6 1.3(6) . . . . ?
C3 C4 C5 C6 -179.1(4) . . . . ?
C4 C5 C6 C7 -0.8(7) . . . . ?
C5 C6 C7 C8 0.4(6) . . . . ?
C5 C6 C7 N1 178.7(4) . . . . ?
C10 N1 C7 C6 162.8(4) . . . . ?
C12 N1 C7 C6 42.3(5) . . . . ?
C11 N1 C7 C6 -76.3(4) . . . . ?
C10 N1 C7 C8 -18.8(5) . . . . ?
C12 N1 C7 C8 -139.3(3) . . . . ?
C11 N1 C7 C8 102.0(4) . . . . ?
C6 C7 C8 C9 -0.4(5) . . . . ?
N1 C7 C8 C9 -178.8(3) . . . . ?
C7 C8 C9 C4 0.9(5) . . . . ?
C5 C4 C9 C8 -1.3(5) . . . . ?
C3 C4 C9 C8 179.1(3) . . . . ?
O4 C13 C14 C15 176.3(3) . . . . ?
O5 C13 C14 C15 -3.6(5) . . . . ?
O4 C13 C14 O6 -2.2(5) . . . . ?
O5 C13 C14 O6 178.0(3) . . . . ?
O6 C14 C15 C16 -0.4(6) . . . . ?
C13 C14 C15 C16 -178.8(3) . . . . ?
C14 C15 C16 C21 -178.3(4) . . . . ?
C14 C15 C16 C17 3.8(6) . . . . ?
C21 C16 C17 C18 0.2(5) . . . . ?
C15 C16 C17 C18 178.2(3) . . . . ?
C16 C17 C18 C19 0.4(5) . . . . ?
C17 C18 C19 C20 -0.2(5) . . . . ?
C17 C18 C19 N2 -180.0(3) . . . . ?
C22 N2 C19 C18 175.8(3) . . . . ?
C24 N2 C19 C18 55.5(4) . . . . ?
C23 N2 C19 C18 -64.7(4) . . . . ?
C22 N2 C19 C20 -4.0(5) . . . . ?
C24 N2 C19 C20 -124.3(4) . . . . ?
C23 N2 C19 C20 115.5(4) . . . . ?
C18 C19 C20 C21 -0.7(6) . . . . ?
N2 C19 C20 C21 179.1(3) . . . . ?
C19 C20 C21 C16 1.4(6) . . . . ?
C17 C16 C21 C20 -1.2(6) . . . . ?
C15 C16 C21 C20 -179.2(4) . . . . ?

_refine_diff_density_max         1.693
_refine_diff_density_min         -1.797
_refine_diff_density_rms         0.140

