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

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

data_cu_20190514_YJ_01_0m_a
_audit_block_doi                 10.5517/ccdc.csd.cc229r49
_database_code_depnum_ccdc_archive 'CCDC 1915990'
loop_
_audit_author_name
_audit_author_address
'Jian Yang'
;Sichuan University
China
;
_audit_update_record             
;
2019-05-14 deposited with the CCDC.	2019-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H21 N O4'
_chemical_formula_weight         279.33

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.3689(3)
_cell_length_b                   10.4011(6)
_cell_length_c                   27.4980(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1535.56(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    7578
_cell_measurement_theta_min      3.21
_cell_measurement_theta_max      64.99

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.717
_shelx_estimated_absorpt_T_min   0.870
_shelx_estimated_absorpt_T_max   0.913
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6263
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_special_details           
;
 The following wavelength and cell were deduced by SADABS from the
 direction cosines etc. They are given here for emergency use only:
 CELL 1.54184    5.368   10.401   27.494   89.971   89.988   90.031
;
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER D8 VENTURE PHOTON II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8783
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.214
_diffrn_reflns_theta_max         64.978
_diffrn_reflns_theta_full        64.978
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2611
_reflns_number_gt                2545
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.674
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.995

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0468P)²+0.1472P] 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_abs_structure_details 
;
 Flack x determined using 1002 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2611
_refine_ls_number_parameters     189
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0868
_refine_ls_wR_factor_gt          0.0860
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_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 0.5610(2) 0.46378(15) 0.26947(4) 0.0504(4) Uani 1 1 d . . . . .
H1 H 0.804(5) 0.480(2) 0.3362(9) 0.053(7) Uiso 1 1 d . . . . .
O002 O 0.2600(3) 0.51199(17) 0.32459(5) 0.0587(4) Uani 1 1 d . . . . .
O003 O 0.9401(3) 0.37026(16) 0.40876(6) 0.0646(5) Uani 1 1 d . . . . .
N004 N 0.6670(3) 0.49868(19) 0.34555(6) 0.0477(4) Uani 1 1 d . . . . .
O005 O 0.7034(5) 0.42029(19) 0.47228(5) 0.0805(6) Uani 1 1 d . . . . .
C006 C 0.4756(3) 0.49288(17) 0.31391(6) 0.0411(4) Uani 1 1 d . . . . .
C007 C 0.6835(3) 0.66209(19) 0.41180(6) 0.0402(4) Uani 1 1 d . . . . .
C008 C 0.5243(4) 0.7262(2) 0.44324(7) 0.0510(5) Uani 1 1 d . . . . .
H008 H 0.381132 0.685365 0.454389 0.061 Uiso 1 1 calc R U . . .
C009 C 0.8969(4) 0.7239(2) 0.39574(7) 0.0479(4) Uani 1 1 d . . . . .
H009 H 1.005839 0.681918 0.374764 0.057 Uiso 1 1 calc R U . . .
C00A C 0.7579(4) 0.43258(19) 0.43036(7) 0.0490(5) Uani 1 1 d . . . . .
C00B C 0.6217(4) 0.52502(19) 0.39655(6) 0.0447(4) Uani 1 1 d . . . . .
H00B H 0.443047 0.512768 0.402150 0.054 Uiso 1 1 calc R U . . .
C00C C 0.3864(4) 0.4366(2) 0.22892(7) 0.0491(5) Uani 1 1 d . . . . .
C00D C 0.5762(5) 0.8501(2) 0.45812(8) 0.0621(6) Uani 1 1 d . . . . .
H00D H 0.467793 0.892576 0.479038 0.075 Uiso 1 1 calc R U . . .
C00E C 0.7870(5) 0.9102(2) 0.44210(8) 0.0623(6) Uani 1 1 d . . . . .
H00E H 0.822073 0.993556 0.452288 0.075 Uiso 1 1 calc R U . . .
C00F C 0.9479(4) 0.8482(2) 0.41094(8) 0.0580(5) Uani 1 1 d . . . . .
H00F H 1.090932 0.889694 0.400094 0.070 Uiso 1 1 calc R U . . .
C00G C 0.2202(5) 0.3249(2) 0.24175(9) 0.0640(6) Uani 1 1 d . . . . .
H00A H 0.126744 0.299428 0.213592 0.096 Uiso 1 1 calc R U . . .
H00C H 0.107639 0.350013 0.267166 0.096 Uiso 1 1 calc R U . . .
H00G H 0.320308 0.254099 0.252681 0.096 Uiso 1 1 calc R U . . .
C00H C 0.5642(5) 0.3993(4) 0.18849(8) 0.0831(9) Uani 1 1 d . . . . .
H00H H 0.471143 0.378960 0.159694 0.125 Uiso 1 1 calc R U . . .
H00I H 0.659370 0.325580 0.198320 0.125 Uiso 1 1 calc R U . . .
H00J H 0.674833 0.469665 0.181863 0.125 Uiso 1 1 calc R U . . .
C00I C 0.2392(6) 0.5559(3) 0.21647(10) 0.0732(7) Uani 1 1 d . . . . .
H00K H 0.350429 0.627642 0.213342 0.110 Uiso 1 1 calc R U . . .
H00L H 0.120823 0.572893 0.241831 0.110 Uiso 1 1 calc R U . . .
H00M H 0.152675 0.542843 0.186313 0.110 Uiso 1 1 calc R U . . .
C00J C 1.0878(6) 0.2828(3) 0.43859(10) 0.0735(7) Uani 1 1 d . . . . .
H00N H 0.979427 0.228043 0.457750 0.088 Uiso 1 1 calc R U . . .
H00O H 1.193566 0.331188 0.460578 0.088 Uiso 1 1 calc R U . . .
C00K C 1.2412(7) 0.2043(3) 0.40543(12) 0.0868(9) Uani 1 1 d . . . . .
H00P H 1.134823 0.158827 0.383264 0.130 Uiso 1 1 calc R U . . .
H00Q H 1.337082 0.143857 0.423990 0.130 Uiso 1 1 calc R U . . .
H00R H 1.351444 0.259287 0.387439 0.130 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 C006 1.340(2) . ?
O001 C00C 1.484(2) . ?
O002 C006 1.210(2) . ?
O003 C00A 1.315(3) . ?
O003 C00J 1.459(3) . ?
N004 C006 1.348(2) . ?
N004 C00B 1.449(2) . ?
N004 H1 0.80(3) . ?
O005 C00A 1.196(2) . ?
C007 C009 1.386(3) . ?
C007 C008 1.387(3) . ?
C007 C00B 1.523(3) . ?
C008 C00D 1.381(3) . ?
C008 H008 0.9300 . ?
C009 C00F 1.386(3) . ?
C009 H009 0.9300 . ?
C00A C00B 1.524(3) . ?
C00B H00B 0.9800 . ?
C00C C00G 1.507(3) . ?
C00C C00I 1.510(4) . ?
C00C C00H 1.516(3) . ?
C00D C00E 1.366(4) . ?
C00D H00D 0.9300 . ?
C00E C00F 1.377(4) . ?
C00E H00E 0.9300 . ?
C00F H00F 0.9300 . ?
C00G H00A 0.9600 . ?
C00G H00C 0.9600 . ?
C00G H00G 0.9600 . ?
C00H H00H 0.9600 . ?
C00H H00I 0.9600 . ?
C00H H00J 0.9600 . ?
C00I H00K 0.9600 . ?
C00I H00L 0.9600 . ?
C00I H00M 0.9600 . ?
C00J C00K 1.475(4) . ?
C00J H00N 0.9700 . ?
C00J H00O 0.9700 . ?
C00K H00P 0.9600 . ?
C00K H00Q 0.9600 . ?
C00K H00R 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
C006 O001 C00C 120.81(14) . . ?
C00A O003 C00J 117.23(18) . . ?
C006 N004 C00B 120.34(16) . . ?
C006 N004 H1 118.8(18) . . ?
C00B N004 H1 120.6(18) . . ?
O002 C006 O001 125.85(16) . . ?
O002 C006 N004 124.41(17) . . ?
O001 C006 N004 109.75(15) . . ?
C009 C007 C008 119.05(19) . . ?
C009 C007 C00B 121.76(17) . . ?
C008 C007 C00B 119.18(18) . . ?
C00D C008 C007 120.6(2) . . ?
C00D C008 H008 119.7 . . ?
C007 C008 H008 119.7 . . ?
C007 C009 C00F 120.0(2) . . ?
C007 C009 H009 120.0 . . ?
C00F C009 H009 120.0 . . ?
O005 C00A O003 124.4(2) . . ?
O005 C00A C00B 122.5(2) . . ?
O003 C00A C00B 113.09(16) . . ?
N004 C00B C007 114.02(16) . . ?
N004 C00B C00A 112.99(17) . . ?
C007 C00B C00A 108.54(14) . . ?
N004 C00B H00B 107.0 . . ?
C007 C00B H00B 107.0 . . ?
C00A C00B H00B 107.0 . . ?
O001 C00C C00G 110.16(17) . . ?
O001 C00C C00I 110.18(18) . . ?
C00G C00C C00I 112.1(2) . . ?
O001 C00C C00H 101.65(16) . . ?
C00G C00C C00H 110.3(2) . . ?
C00I C00C C00H 112.0(2) . . ?
C00E C00D C008 119.9(2) . . ?
C00E C00D H00D 120.0 . . ?
C008 C00D H00D 120.0 . . ?
C00D C00E C00F 120.4(2) . . ?
C00D C00E H00E 119.8 . . ?
C00F C00E H00E 119.8 . . ?
C00E C00F C009 120.1(2) . . ?
C00E C00F H00F 120.0 . . ?
C009 C00F H00F 120.0 . . ?
C00C C00G H00A 109.5 . . ?
C00C C00G H00C 109.5 . . ?
H00A C00G H00C 109.5 . . ?
C00C C00G H00G 109.5 . . ?
H00A C00G H00G 109.5 . . ?
H00C C00G H00G 109.5 . . ?
C00C C00H H00H 109.5 . . ?
C00C C00H H00I 109.5 . . ?
H00H C00H H00I 109.5 . . ?
C00C C00H H00J 109.5 . . ?
H00H C00H H00J 109.5 . . ?
H00I C00H H00J 109.5 . . ?
C00C C00I H00K 109.5 . . ?
C00C C00I H00L 109.5 . . ?
H00K C00I H00L 109.5 . . ?
C00C C00I H00M 109.5 . . ?
H00K C00I H00M 109.5 . . ?
H00L C00I H00M 109.5 . . ?
O003 C00J C00K 107.5(2) . . ?
O003 C00J H00N 110.2 . . ?
C00K C00J H00N 110.2 . . ?
O003 C00J H00O 110.2 . . ?
C00K C00J H00O 110.2 . . ?
H00N C00J H00O 108.5 . . ?
C00J C00K H00P 109.5 . . ?
C00J C00K H00Q 109.5 . . ?
H00P C00K H00Q 109.5 . . ?
C00J C00K H00R 109.5 . . ?
H00P C00K H00R 109.5 . . ?
H00Q C00K H00R 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
C00C O001 C006 O002 -7.4(3) . . . . ?
C00C O001 C006 N004 172.92(18) . . . . ?
C00B N004 C006 O002 2.2(3) . . . . ?
C00B N004 C006 O001 -178.17(17) . . . . ?
C009 C007 C008 C00D 0.4(3) . . . . ?
C00B C007 C008 C00D 179.39(18) . . . . ?
C008 C007 C009 C00F -0.3(3) . . . . ?
C00B C007 C009 C00F -179.22(18) . . . . ?
C00J O003 C00A O005 -1.5(3) . . . . ?
C00J O003 C00A C00B 177.8(2) . . . . ?
C006 N004 C00B C007 -103.2(2) . . . . ?
C006 N004 C00B C00A 132.2(2) . . . . ?
C009 C007 C00B N004 -42.4(2) . . . . ?
C008 C007 C00B N004 138.67(18) . . . . ?
C009 C007 C00B C00A 84.5(2) . . . . ?
C008 C007 C00B C00A -94.4(2) . . . . ?
O005 C00A C00B N004 -163.3(2) . . . . ?
O003 C00A C00B N004 17.4(2) . . . . ?
O005 C00A C00B C007 69.2(3) . . . . ?
O003 C00A C00B C007 -110.06(19) . . . . ?
C006 O001 C00C C00G -58.7(2) . . . . ?
C006 O001 C00C C00I 65.5(2) . . . . ?
C006 O001 C00C C00H -175.7(2) . . . . ?
C007 C008 C00D C00E -0.4(3) . . . . ?
C008 C00D C00E C00F 0.3(3) . . . . ?
C00D C00E C00F C009 -0.2(3) . . . . ?
C007 C009 C00F C00E 0.2(3) . . . . ?
C00A O003 C00J C00K 168.0(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N004 H1 O002 0.80(3) 2.49(3) 3.239(2) 155(2) 1_655
C00G H00C O002 0.96 2.45 3.004(3) 116.5 .
C00I H00L O002 0.96 2.48 3.010(3) 114.9 .

_refine_diff_density_max         0.114
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_20190617_YJ_01_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1935053'
loop_
_audit_author_name
_audit_author_address
'Jian Yang'
;Sichuan University
China
;
_audit_update_record             
;
2019-06-19 deposited with the CCDC.	2019-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H46 N4 O'
_chemical_formula_weight         526.75

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   11.3578(2)
_cell_length_b                   16.0040(2)
_cell_length_c                   16.8541(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3063.57(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    9975
_cell_measurement_theta_min      3.81
_cell_measurement_theta_max      65.11

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.142
_exptl_crystal_F_000             1144
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.533
_shelx_estimated_absorpt_T_min   0.883
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6734
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_special_details           
;
 The following wavelength and cell were deduced by SADABS from the
 direction cosines etc. They are given here for emergency use only:
 CELL 1.54184   11.359   16.015   16.856   89.997   90.010   90.019
;
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER D8 VENTURE PHOTON II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17635
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.809
_diffrn_reflns_theta_max         65.143
_diffrn_reflns_theta_full        65.143
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             5169
_reflns_number_gt                4987
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.771
_reflns_Friedel_fraction_max     0.986
_reflns_Friedel_fraction_full    0.986

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0786P)²+0.1671P] 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_abs_structure_details 
;
 Flack x determined using 2097 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5169
_refine_ls_number_parameters     356
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1101
_refine_ls_wR_factor_gt          0.1071
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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
O1 O 0.77334(17) 0.47762(11) 0.09558(9) 0.0518(4) Uani 1 1 d . . . . .
H1 H 0.818(2) 0.5884(16) 0.2304(18) 0.037(6) Uiso 1 1 d . . . . .
C1 C 0.6231(2) 0.31715(19) 0.2540(2) 0.0659(8) Uani 1 1 d . . . . .
H1A H 0.562823 0.304776 0.293005 0.079 Uiso 1 1 calc R U . . .
H1B H 0.596592 0.363663 0.221694 0.079 Uiso 1 1 calc R U . . .
N1 N 0.79741(16) 0.57867(11) 0.18730(11) 0.0394(4) Uani 1 1 d . . . . .
N2 N 0.77548(14) 0.42745(10) 0.28996(9) 0.0340(4) Uani 1 1 d . . . . .
C2 C 0.6457(3) 0.2421(2) 0.2030(2) 0.0744(8) Uani 1 1 d . . . . .
H2A H 0.591182 0.197693 0.216497 0.089 Uiso 1 1 calc R U . . .
H2B H 0.634662 0.256303 0.147506 0.089 Uiso 1 1 calc R U . . .
N4 N 0.72304(15) 0.45378(11) 0.42204(9) 0.0371(4) Uani 1 1 d . . . . .
H41 H 0.754573 0.438607 0.466133 0.045 Uiso 1 1 calc R U . . .
C4 C 0.8337(2) 0.28934(14) 0.25063(15) 0.0474(5) Uani 1 1 d . . . . .
H4 H 0.897540 0.272108 0.286171 0.057 Uiso 1 1 calc R U . . .
N3 N 0.87070(17) 0.53472(13) 0.35479(10) 0.0445(4) Uani 1 1 d . . . . .
C3 C 0.7692(3) 0.21404(16) 0.2168(2) 0.0676(8) Uani 1 1 d . . . . .
H3A H 0.805176 0.196203 0.167431 0.081 Uiso 1 1 calc R U . . .
H3B H 0.771006 0.167817 0.253997 0.081 Uiso 1 1 calc R U . . .
C6 C 0.8775(2) 0.35128(13) 0.18817(14) 0.0460(5) Uani 1 1 d . . . . .
H6A H 0.960387 0.342235 0.177253 0.055 Uiso 1 1 calc R U . . .
H6B H 0.833732 0.344715 0.139145 0.055 Uiso 1 1 calc R U . . .
C5 C 0.7394(2) 0.33910(13) 0.29533(12) 0.0413(5) Uani 1 1 d . . . . .
H5 H 0.736757 0.321507 0.350994 0.050 Uiso 1 1 calc R U . . .
C7 C 0.85799(17) 0.43839(12) 0.22273(11) 0.0347(4) Uani 1 1 d . . . . .
H7 H 0.932953 0.460469 0.242479 0.042 Uiso 1 1 calc R U . . .
C8 C 0.80597(18) 0.49934(13) 0.16187(11) 0.0357(4) Uani 1 1 d . . . . .
C9 C 0.73266(19) 0.64071(13) 0.14118(12) 0.0390(4) Uani 1 1 d . . . . .
H9 H 0.763506 0.638649 0.086912 0.047 Uiso 1 1 calc R U . . .
C10 C 0.6015(2) 0.62124(14) 0.13648(13) 0.0416(5) Uani 1 1 d . . . . .
C11 C 0.5340(3) 0.65802(18) 0.07738(16) 0.0571(6) Uani 1 1 d . . . . .
H11 H 0.569198 0.694533 0.041620 0.069 Uiso 1 1 calc R U . . .
C13 C 0.3615(2) 0.5877(2) 0.12265(18) 0.0661(7) Uani 1 1 d . . . . .
H13 H 0.281346 0.576686 0.118352 0.079 Uiso 1 1 calc R U . . .
C14 C 0.4279(3) 0.5501(2) 0.18161(18) 0.0627(7) Uani 1 1 d . . . . .
H14 H 0.392343 0.513157 0.216816 0.075 Uiso 1 1 calc R U . . .
C15 C 0.5467(2) 0.56732(17) 0.18832(14) 0.0513(5) Uani 1 1 d . . . . .
H15 H 0.590204 0.542103 0.228448 0.062 Uiso 1 1 calc R U . . .
C16 C 0.75896(19) 0.72760(14) 0.17346(12) 0.0407(5) Uani 1 1 d . . . . .
C17 C 0.8478(2) 0.77508(17) 0.14013(17) 0.0537(6) Uani 1 1 d . . . . .
H17 H 0.891760 0.753437 0.098379 0.064 Uiso 1 1 calc R U . . .
C18 C 0.8720(3) 0.85488(19) 0.1684(2) 0.0686(8) Uani 1 1 d . . . . .
H18 H 0.931048 0.886633 0.144908 0.082 Uiso 1 1 calc R U . . .
C19 C 0.8093(3) 0.88668(18) 0.2304(2) 0.0704(8) Uani 1 1 d . . . . .
H19 H 0.825910 0.939937 0.249441 0.085 Uiso 1 1 calc R U . . .
C20 C 0.7217(3) 0.83994(18) 0.2648(2) 0.0668(7) Uani 1 1 d . . . . .
H20 H 0.679624 0.861491 0.307434 0.080 Uiso 1 1 calc R U . . .
C21 C 0.6955(2) 0.76094(16) 0.23628(15) 0.0518(5) Uani 1 1 d . . . . .
H21 H 0.635183 0.730093 0.259370 0.062 Uiso 1 1 calc R U . . .
C22 C 0.79360(16) 0.47595(12) 0.35756(11) 0.0334(4) Uani 1 1 d . . . . .
C23 C 0.8905(2) 0.58940(15) 0.42271(12) 0.0459(5) Uani 1 1 d . . . . .
H23 H 0.827104 0.581411 0.461434 0.055 Uiso 1 1 calc R U . . .
C24 C 0.8915(3) 0.68007(17) 0.39537(17) 0.0631(7) Uani 1 1 d . . . . .
H24A H 0.815095 0.694270 0.373403 0.076 Uiso 1 1 calc R U . . .
H24B H 0.949844 0.687014 0.353892 0.076 Uiso 1 1 calc R U . . .
C25 C 0.9198(4) 0.73926(19) 0.46441(18) 0.0715(8) Uani 1 1 d . . . . .
H25A H 0.924311 0.796129 0.444733 0.086 Uiso 1 1 calc R U . . .
H25B H 0.856839 0.736740 0.503225 0.086 Uiso 1 1 calc R U . . .
C26 C 1.0328(3) 0.7169(2) 0.50312(18) 0.0708(8) Uani 1 1 d . . . . .
H26A H 1.044260 0.752457 0.549077 0.085 Uiso 1 1 calc R U . . .
H26B H 1.096828 0.727536 0.466409 0.085 Uiso 1 1 calc R U . . .
C27 C 1.0375(4) 0.6269(2) 0.5289(2) 0.0858(11) Uani 1 1 d . . . . .
H27A H 0.982629 0.618257 0.572274 0.103 Uiso 1 1 calc R U . . .
H27B H 1.115948 0.614080 0.548125 0.103 Uiso 1 1 calc R U . . .
C28 C 1.0066(3) 0.56795(19) 0.46058(19) 0.0696(8) Uani 1 1 d . . . . .
H28A H 1.068102 0.570668 0.420763 0.084 Uiso 1 1 calc R U . . .
H28B H 1.003405 0.511091 0.480390 0.084 Uiso 1 1 calc R U . . .
C29 C 0.59388(17) 0.45667(13) 0.41372(11) 0.0359(4) Uani 1 1 d . . . . .
H29 H 0.573822 0.437580 0.360150 0.043 Uiso 1 1 calc R U . . .
C30 C 0.5451(2) 0.54497(15) 0.42405(14) 0.0473(5) Uani 1 1 d . . . . .
H30A H 0.569375 0.566686 0.475237 0.057 Uiso 1 1 calc R U . . .
H30B H 0.577856 0.580963 0.383325 0.057 Uiso 1 1 calc R U . . .
C31 C 0.4111(2) 0.54667(18) 0.41867(17) 0.0585(6) Uani 1 1 d . . . . .
H31A H 0.383331 0.602929 0.429014 0.070 Uiso 1 1 calc R U . . .
H31B H 0.387164 0.531433 0.365358 0.070 Uiso 1 1 calc R U . . .
C32 C 0.3554(2) 0.48713(19) 0.47744(18) 0.0614(7) Uani 1 1 d . . . . .
H32A H 0.270744 0.486911 0.469996 0.074 Uiso 1 1 calc R U . . .
H32B H 0.371616 0.506142 0.530985 0.074 Uiso 1 1 calc R U . . .
C33 C 0.4030(2) 0.39864(18) 0.46689(19) 0.0583(6) Uani 1 1 d . . . . .
H33A H 0.369675 0.362579 0.507334 0.070 Uiso 1 1 calc R U . . .
H33B H 0.379144 0.377287 0.415474 0.070 Uiso 1 1 calc R U . . .
C34 C 0.53673(19) 0.39711(14) 0.47292(14) 0.0439(5) Uani 1 1 d . . . . .
H34A H 0.564667 0.340774 0.463093 0.053 Uiso 1 1 calc R U . . .
H34B H 0.560026 0.412678 0.526284 0.053 Uiso 1 1 calc R U . . .
C12 C 0.4150(3) 0.6411(2) 0.07102(19) 0.0701(8) Uani 1 1 d . . . . .
H12 H 0.371136 0.666306 0.031097 0.084 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 C8 1.227(3) . ?
C1 C2 1.499(4) . ?
C1 C5 1.534(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
N1 C8 1.344(3) . ?
N1 C9 1.460(3) . ?
N1 H1 0.78(3) . ?
N2 C22 1.394(2) . ?
N2 C5 1.475(3) . ?
N2 C7 1.481(2) . ?
C2 C3 1.491(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
N4 C22 1.396(3) . ?
N4 C29 1.474(3) . ?
N4 H41 0.8600 . ?
C4 C3 1.522(4) . ?
C4 C6 1.529(3) . ?
C4 C5 1.533(3) . ?
C4 H4 0.9800 . ?
N3 C22 1.286(3) . ?
N3 C23 1.458(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C6 C7 1.527(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C5 H5 0.9800 . ?
C7 C8 1.534(3) . ?
C7 H7 0.9800 . ?
C9 C16 1.523(3) . ?
C9 C10 1.524(3) . ?
C9 H9 0.9800 . ?
C10 C15 1.377(3) . ?
C10 C11 1.388(3) . ?
C11 C12 1.382(4) . ?
C11 H11 0.9300 . ?
C13 C12 1.362(5) . ?
C13 C14 1.385(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.382(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.382(4) . ?
C16 C21 1.387(3) . ?
C17 C18 1.390(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.363(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.373(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.385(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C23 C28 1.504(4) . ?
C23 C24 1.522(4) . ?
C23 H23 0.9800 . ?
C24 C25 1.535(4) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.483(5) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 C27 1.505(5) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C28 1.530(4) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 C34 1.525(3) . ?
C29 C30 1.528(3) . ?
C29 H29 0.9800 . ?
C30 C31 1.525(4) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 C32 1.513(4) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.526(4) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 C34 1.523(3) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C5 107.3(2) . . ?
C2 C1 H1A 110.3 . . ?
C5 C1 H1A 110.3 . . ?
C2 C1 H1B 110.3 . . ?
C5 C1 H1B 110.3 . . ?
H1A C1 H1B 108.5 . . ?
C8 N1 C9 120.62(18) . . ?
C8 N1 H1 117.7(19) . . ?
C9 N1 H1 120.7(19) . . ?
C22 N2 C5 121.65(15) . . ?
C22 N2 C7 117.78(15) . . ?
C5 N2 C7 109.64(15) . . ?
C3 C2 C1 108.2(2) . . ?
C3 C2 H2A 110.1 . . ?
C1 C2 H2A 110.1 . . ?
C3 C2 H2B 110.1 . . ?
C1 C2 H2B 110.1 . . ?
H2A C2 H2B 108.4 . . ?
C22 N4 C29 119.29(16) . . ?
C22 N4 H41 120.4 . . ?
C29 N4 H41 120.4 . . ?
C3 C4 C6 114.3(2) . . ?
C3 C4 C5 105.0(2) . . ?
C6 C4 C5 103.23(17) . . ?
C3 C4 H4 111.3 . . ?
C6 C4 H4 111.3 . . ?
C5 C4 H4 111.3 . . ?
C22 N3 C23 121.02(18) . . ?
C2 C3 C4 105.9(2) . . ?
C2 C3 H3A 110.6 . . ?
C4 C3 H3A 110.6 . . ?
C2 C3 H3B 110.6 . . ?
C4 C3 H3B 110.6 . . ?
H3A C3 H3B 108.7 . . ?
C7 C6 C4 106.38(17) . . ?
C7 C6 H6A 110.5 . . ?
C4 C6 H6A 110.5 . . ?
C7 C6 H6B 110.5 . . ?
C4 C6 H6B 110.5 . . ?
H6A C6 H6B 108.6 . . ?
N2 C5 C4 105.89(17) . . ?
N2 C5 C1 115.5(2) . . ?
C4 C5 C1 105.03(18) . . ?
N2 C5 H5 110.0 . . ?
C4 C5 H5 110.0 . . ?
C1 C5 H5 110.0 . . ?
N2 C7 C6 106.01(16) . . ?
N2 C7 C8 110.07(15) . . ?
C6 C7 C8 112.41(17) . . ?
N2 C7 H7 109.4 . . ?
C6 C7 H7 109.4 . . ?
C8 C7 H7 109.4 . . ?
O1 C8 N1 122.42(19) . . ?
O1 C8 C7 123.03(19) . . ?
N1 C8 C7 114.54(17) . . ?
N1 C9 C16 109.40(17) . . ?
N1 C9 C10 112.40(17) . . ?
C16 C9 C10 113.40(18) . . ?
N1 C9 H9 107.1 . . ?
C16 C9 H9 107.1 . . ?
C10 C9 H9 107.1 . . ?
C15 C10 C11 118.1(2) . . ?
C15 C10 C9 122.5(2) . . ?
C11 C10 C9 119.4(2) . . ?
C12 C11 C10 120.8(3) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C12 C13 C14 119.2(3) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C15 C14 C13 120.3(3) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C10 C15 C14 121.0(2) . . ?
C10 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C17 C16 C21 118.5(2) . . ?
C17 C16 C9 120.0(2) . . ?
C21 C16 C9 121.5(2) . . ?
C16 C17 C18 120.7(3) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C19 C18 C17 120.1(3) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C20 119.9(3) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C19 C20 C21 120.5(3) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C16 120.3(3) . . ?
C20 C21 H21 119.9 . . ?
C16 C21 H21 119.9 . . ?
N3 C22 N2 118.57(17) . . ?
N3 C22 N4 127.23(18) . . ?
N2 C22 N4 114.20(16) . . ?
N3 C23 C28 109.3(2) . . ?
N3 C23 C24 109.60(19) . . ?
C28 C23 C24 109.8(2) . . ?
N3 C23 H23 109.3 . . ?
C28 C23 H23 109.3 . . ?
C24 C23 H23 109.3 . . ?
C23 C24 C25 111.1(2) . . ?
C23 C24 H24A 109.4 . . ?
C25 C24 H24A 109.4 . . ?
C23 C24 H24B 109.4 . . ?
C25 C24 H24B 109.4 . . ?
H24A C24 H24B 108.0 . . ?
C26 C25 C24 111.5(3) . . ?
C26 C25 H25A 109.3 . . ?
C24 C25 H25A 109.3 . . ?
C26 C25 H25B 109.3 . . ?
C24 C25 H25B 109.3 . . ?
H25A C25 H25B 108.0 . . ?
C25 C26 C27 112.9(3) . . ?
C25 C26 H26A 109.0 . . ?
C27 C26 H26A 109.0 . . ?
C25 C26 H26B 109.0 . . ?
C27 C26 H26B 109.0 . . ?
H26A C26 H26B 107.8 . . ?
C26 C27 C28 111.4(3) . . ?
C26 C27 H27A 109.4 . . ?
C28 C27 H27A 109.4 . . ?
C26 C27 H27B 109.4 . . ?
C28 C27 H27B 109.4 . . ?
H27A C27 H27B 108.0 . . ?
C23 C28 C27 112.3(3) . . ?
C23 C28 H28A 109.1 . . ?
C27 C28 H28A 109.1 . . ?
C23 C28 H28B 109.1 . . ?
C27 C28 H28B 109.1 . . ?
H28A C28 H28B 107.9 . . ?
N4 C29 C34 109.98(17) . . ?
N4 C29 C30 112.25(18) . . ?
C34 C29 C30 110.45(17) . . ?
N4 C29 H29 108.0 . . ?
C34 C29 H29 108.0 . . ?
C30 C29 H29 108.0 . . ?
C31 C30 C29 111.8(2) . . ?
C31 C30 H30A 109.3 . . ?
C29 C30 H30A 109.3 . . ?
C31 C30 H30B 109.3 . . ?
C29 C30 H30B 109.3 . . ?
H30A C30 H30B 107.9 . . ?
C32 C31 C30 111.5(2) . . ?
C32 C31 H31A 109.3 . . ?
C30 C31 H31A 109.3 . . ?
C32 C31 H31B 109.3 . . ?
C30 C31 H31B 109.3 . . ?
H31A C31 H31B 108.0 . . ?
C31 C32 C33 111.1(2) . . ?
C31 C32 H32A 109.4 . . ?
C33 C32 H32A 109.4 . . ?
C31 C32 H32B 109.4 . . ?
C33 C32 H32B 109.4 . . ?
H32A C32 H32B 108.0 . . ?
C34 C33 C32 111.1(2) . . ?
C34 C33 H33A 109.4 . . ?
C32 C33 H33A 109.4 . . ?
C34 C33 H33B 109.4 . . ?
C32 C33 H33B 109.4 . . ?
H33A C33 H33B 108.0 . . ?
C33 C34 C29 111.8(2) . . ?
C33 C34 H34A 109.3 . . ?
C29 C34 H34A 109.3 . . ?
C33 C34 H34B 109.3 . . ?
C29 C34 H34B 109.3 . . ?
H34A C34 H34B 107.9 . . ?
C13 C12 C11 120.7(3) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?

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
C5 C1 C2 C3 4.3(4) . . . . ?
C1 C2 C3 C4 -21.1(4) . . . . ?
C6 C4 C3 C2 -82.8(3) . . . . ?
C5 C4 C3 C2 29.6(3) . . . . ?
C3 C4 C6 C7 141.1(2) . . . . ?
C5 C4 C6 C7 27.6(2) . . . . ?
C22 N2 C5 C4 -122.85(19) . . . . ?
C7 N2 C5 C4 20.4(2) . . . . ?
C22 N2 C5 C1 121.4(2) . . . . ?
C7 N2 C5 C1 -95.4(2) . . . . ?
C3 C4 C5 N2 -149.4(2) . . . . ?
C6 C4 C5 N2 -29.3(2) . . . . ?
C3 C4 C5 C1 -26.7(3) . . . . ?
C6 C4 C5 C1 93.4(2) . . . . ?
C2 C1 C5 N2 130.3(3) . . . . ?
C2 C1 C5 C4 14.0(3) . . . . ?
C22 N2 C7 C6 142.00(18) . . . . ?
C5 N2 C7 C6 -2.9(2) . . . . ?
C22 N2 C7 C8 -96.19(19) . . . . ?
C5 N2 C7 C8 118.95(17) . . . . ?
C4 C6 C7 N2 -15.9(2) . . . . ?
C4 C6 C7 C8 -136.17(19) . . . . ?
C9 N1 C8 O1 9.1(3) . . . . ?
C9 N1 C8 C7 -170.09(18) . . . . ?
N2 C7 C8 O1 -111.2(2) . . . . ?
C6 C7 C8 O1 6.7(3) . . . . ?
N2 C7 C8 N1 68.0(2) . . . . ?
C6 C7 C8 N1 -174.12(18) . . . . ?
C8 N1 C9 C16 -167.86(19) . . . . ?
C8 N1 C9 C10 65.2(2) . . . . ?
N1 C9 C10 C15 18.1(3) . . . . ?
C16 C9 C10 C15 -106.6(2) . . . . ?
N1 C9 C10 C11 -161.1(2) . . . . ?
C16 C9 C10 C11 74.2(3) . . . . ?
C15 C10 C11 C12 0.2(4) . . . . ?
C9 C10 C11 C12 179.4(3) . . . . ?
C12 C13 C14 C15 0.7(5) . . . . ?
C11 C10 C15 C14 0.2(4) . . . . ?
C9 C10 C15 C14 -179.0(2) . . . . ?
C13 C14 C15 C10 -0.6(4) . . . . ?
N1 C9 C16 C17 94.0(2) . . . . ?
C10 C9 C16 C17 -139.7(2) . . . . ?
N1 C9 C16 C21 -86.0(2) . . . . ?
C10 C9 C16 C21 40.4(3) . . . . ?
C21 C16 C17 C18 -0.8(4) . . . . ?
C9 C16 C17 C18 179.3(2) . . . . ?
C16 C17 C18 C19 1.1(4) . . . . ?
C17 C18 C19 C20 -0.4(5) . . . . ?
C18 C19 C20 C21 -0.7(5) . . . . ?
C19 C20 C21 C16 1.0(4) . . . . ?
C17 C16 C21 C20 -0.3(4) . . . . ?
C9 C16 C21 C20 179.6(2) . . . . ?
C23 N3 C22 N2 177.77(19) . . . . ?
C23 N3 C22 N4 -2.1(4) . . . . ?
C5 N2 C22 N3 149.1(2) . . . . ?
C7 N2 C22 N3 8.7(3) . . . . ?
C5 N2 C22 N4 -30.9(3) . . . . ?
C7 N2 C22 N4 -171.39(17) . . . . ?
C29 N4 C22 N3 120.8(2) . . . . ?
C29 N4 C22 N2 -59.2(2) . . . . ?
C22 N3 C23 C28 107.5(3) . . . . ?
C22 N3 C23 C24 -132.0(2) . . . . ?
N3 C23 C24 C25 -176.4(3) . . . . ?
C28 C23 C24 C25 -56.3(3) . . . . ?
C23 C24 C25 C26 55.7(4) . . . . ?
C24 C25 C26 C27 -53.8(4) . . . . ?
C25 C26 C27 C28 52.5(5) . . . . ?
N3 C23 C28 C27 176.0(3) . . . . ?
C24 C23 C28 C27 55.7(4) . . . . ?
C26 C27 C28 C23 -53.7(5) . . . . ?
C22 N4 C29 C34 155.41(18) . . . . ?
C22 N4 C29 C30 -81.2(2) . . . . ?
N4 C29 C30 C31 -177.69(18) . . . . ?
C34 C29 C30 C31 -54.6(3) . . . . ?
C29 C30 C31 C32 55.2(3) . . . . ?
C30 C31 C32 C33 -55.2(3) . . . . ?
C31 C32 C33 C34 55.5(3) . . . . ?
C32 C33 C34 C29 -55.8(3) . . . . ?
N4 C29 C34 C33 179.5(2) . . . . ?
C30 C29 C34 C33 55.1(3) . . . . ?
C14 C13 C12 C11 -0.3(5) . . . . ?
C10 C11 C12 C13 -0.1(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 N3 0.78(3) 2.35(3) 3.026(3) 147(2) .
N4 H41 O1 0.86 2.58 3.125(2) 122.2 2_665

_refine_diff_density_max         0.161
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.060

