# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_dan8114
_database_code_depnum_ccdc_archive 'CCDC 1546596'
_audit_update_record             
;
2017-04-27 deposited with the CCDC.
2017-07-18 downloaded from the CCDC.
;

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H27 N3 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         389.48
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      tetragonal
_space_group_name_H-M_alt        'P 43'
_space_group_name_Hall           'P 4cw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+3/4'
'y, -x, z+1/4'

_cell_length_a                   13.7270(3)
_cell_length_b                   13.7270(3)
_cell_length_c                   10.9453(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2062.43(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9895
_cell_measurement_theta_min      5.1684
_cell_measurement_theta_max      68.2882
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.288
_exptl_crystal_size_mid          0.266
_exptl_crystal_size_min          0.142
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832

_exptl_absorpt_coefficient_mu    0.640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/2, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_T_max  0.92

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            25621
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_theta_min         3.22
_diffrn_reflns_theta_max         68.39
_diffrn_reflns_theta_full        68.39
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       13

_refine_special_details          
;
;

_reflns_number_total             3636
_reflns_number_gt                3579
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0260
_refine_ls_wR_factor_gt          0.0636
_refine_ls_wR_factor_ref         0.0643
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.103
_refine_ls_number_reflns         3636
_refine_ls_number_parameters     262
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0340P)²+0.3333P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.107
_refine_diff_density_min         -0.156
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Flack x determined using 1598 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(5)

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'

_computing_data_collection       
;
APEX2 v.2014.1-1 (Bruker AXS Inc., 2014)

;
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.91345(11) 0.49227(11) 0.37032(17) 0.0152(3) Uani d . . . 1 . .
H H1 0.982 0.5077 0.3461 0.018 Uiso calc U . R 1 . .
O O1 0.68177(8) 0.59616(8) 0.30288(12) 0.0197(3) Uani d . . . 1 . .
N N2 0.84481(9) 0.56073(9) 0.31325(14) 0.0157(3) Uani d . . . 1 . .
O O2 0.96858(8) 0.51130(8) 0.58141(13) 0.0208(3) Uani d . . . 1 . .
C C3 0.74999(11) 0.54883(11) 0.34391(16) 0.0149(3) Uani d . . . 1 . .
C C4 0.74141(11) 0.46531(11) 0.43403(16) 0.0150(3) Uani d . . . 1 . .
H H4 0.6726 0.4572 0.4621 0.018 Uiso calc U . R 1 . .
N N5 0.80664(10) 0.48595(10) 0.53807(14) 0.0158(3) Uani d . . . 1 . .
C C6 0.90152(12) 0.49775(11) 0.50864(16) 0.0158(4) Uani d . . . 1 . .
C C7 0.88487(11) 0.38845(11) 0.32815(17) 0.0146(3) Uani d . . . 1 . .
H H7 0.888 0.3847 0.237 0.018 Uiso calc U . R 1 . .
C C8 0.77852(11) 0.37188(12) 0.37086(17) 0.0167(4) Uani d . . . 1 . .
H H8A 0.7367 0.3563 0.2998 0.02 Uiso calc U . R 1 . .
H H8B 0.7759 0.3164 0.4286 0.02 Uiso calc U . R 1 . .
C C9 0.87840(12) 0.62902(12) 0.22074(17) 0.0168(4) Uani d . . . 1 . .
H H9A 0.8224 0.6684 0.1922 0.02 Uiso calc U . R 1 . .
H H9B 0.9037 0.592 0.1499 0.02 Uiso calc U . R 1 . .
C C10 0.77022(12) 0.47883(13) 0.66285(16) 0.0191(4) Uani d . . . 1 . .
H H10A 0.8263 0.4793 0.7197 0.023 Uiso calc U . R 1 . .
H H10B 0.7363 0.4156 0.6727 0.023 Uiso calc U . R 1 . .
C C11 0.95729(12) 0.69682(11) 0.26675(17) 0.0156(4) Uani d . . . 1 . .
C C12 0.96284(12) 0.72614(12) 0.38793(18) 0.0183(4) Uani d . . . 1 . .
H H12 0.9179 0.7011 0.446 0.022 Uiso calc U . R 1 . .
C C13 1.03406(13) 0.79208(13) 0.42457(19) 0.0221(4) Uani d . . . 1 . .
H H13 1.0378 0.8115 0.5077 0.027 Uiso calc U . R 1 . .
C C14 1.09950(14) 0.82957(14) 0.3407(2) 0.0279(4) Uani d . . . 1 . .
H H14 1.1467 0.8762 0.3654 0.034 Uiso calc U . R 1 . .
C C15 1.09554(15) 0.79839(16) 0.2204(2) 0.0311(5) Uani d . . . 1 . .
H H15 1.141 0.8229 0.1626 0.037 Uiso calc U . R 1 . .
C C16 1.02560(13) 0.73158(13) 0.18388(19) 0.0231(4) Uani d . . . 1 . .
H H16 1.0244 0.7094 0.1017 0.028 Uiso calc U . R 1 . .
C C21 0.70088(12) 0.56013(13) 0.69842(16) 0.0183(4) Uani d . . . 1 . .
C C22 0.62181(13) 0.53910(14) 0.77371(18) 0.0239(4) Uani d . . . 1 . .
H H22 0.6093 0.4736 0.7969 0.029 Uiso calc U . R 1 . .
C C23 0.56114(14) 0.61299(15) 0.81522(19) 0.0292(4) Uani d . . . 1 . .
H H23 0.508 0.5979 0.8675 0.035 Uiso calc U . R 1 . .
C C24 0.57785(14) 0.70850(15) 0.7806(2) 0.0300(5) Uani d . . . 1 . .
H H24 0.5367 0.7591 0.8098 0.036 Uiso calc U . R 1 . .
C C25 0.65471(14) 0.73016(14) 0.7032(2) 0.0278(4) Uani d . . . 1 . .
H H25 0.6654 0.7955 0.6778 0.033 Uiso calc U . R 1 . .
C C26 0.71637(12) 0.65618(13) 0.66269(18) 0.0223(4) Uani d . . . 1 . .
H H26 0.7694 0.6715 0.6103 0.027 Uiso calc U . R 1 . .
N N31 0.95127(10) 0.31682(9) 0.38115(14) 0.0149(3) Uani d . . . 1 . .
C C32 0.93084(13) 0.21657(12) 0.34162(18) 0.0196(4) Uani d . . . 1 . .
H H32A 0.9228 0.2132 0.2518 0.024 Uiso calc U . R 1 . .
H H32B 0.8712 0.1912 0.3812 0.024 Uiso calc U . R 1 . .
C C33 1.02075(13) 0.15935(12) 0.38275(19) 0.0232(4) Uani d . . . 1 . .
H H33A 1.0362 0.1066 0.3242 0.028 Uiso calc U . R 1 . .
H H33B 1.0105 0.1306 0.4647 0.028 Uiso calc U . R 1 . .
C C34 1.10280(13) 0.23617(12) 0.38567(19) 0.0214(4) Uani d . . . 1 . .
H H34A 1.13 0.2426 0.4691 0.026 Uiso calc U . R 1 . .
H H34B 1.156 0.2183 0.3289 0.026 Uiso calc U . R 1 . .
C C35 1.05374(11) 0.33079(12) 0.34548(18) 0.0190(4) Uani d . . . 1 . .
H H35A 1.0825 0.3876 0.3879 0.023 Uiso calc U . R 1 . .
H H35B 1.0598 0.3403 0.2561 0.023 Uiso calc U . R 1 . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N2 . 1.470(2) ?
C1 C6 . 1.525(2) ?
C1 C7 . 1.549(2) ?
C1 H1 . 1.0 ?
O1 C3 . 1.225(2) ?
N2 C3 . 1.354(2) ?
N2 C9 . 1.455(2) ?
O2 C6 . 1.231(2) ?
C3 C4 . 1.517(2) ?
C4 N5 . 1.476(2) ?
C4 C8 . 1.544(2) ?
C4 H4 . 1.0 ?
N5 C6 . 1.352(2) ?
N5 C10 . 1.458(2) ?
C7 N31 . 1.461(2) ?
C7 C8 . 1.550(2) ?
C7 H7 . 1.0 ?
C8 H8A . 0.99 ?
C8 H8B . 0.99 ?
C9 C11 . 1.514(2) ?
C9 H9A . 0.99 ?
C9 H9B . 0.99 ?
C10 C21 . 1.518(2) ?
C10 H10A . 0.99 ?
C10 H10B . 0.99 ?
C11 C12 . 1.388(3) ?
C11 C16 . 1.389(3) ?
C12 C13 . 1.391(2) ?
C12 H12 . 0.95 ?
C13 C14 . 1.383(3) ?
C13 H13 . 0.95 ?
C14 C15 . 1.386(3) ?
C14 H14 . 0.95 ?
C15 C16 . 1.387(3) ?
C15 H15 . 0.95 ?
C16 H16 . 0.95 ?
C21 C26 . 1.392(3) ?
C21 C22 . 1.393(3) ?
C22 C23 . 1.389(3) ?
C22 H22 . 0.95 ?
C23 C24 . 1.384(3) ?
C23 H23 . 0.95 ?
C24 C25 . 1.385(3) ?
C24 H24 . 0.95 ?
C25 C26 . 1.394(3) ?
C25 H25 . 0.95 ?
C26 H26 . 0.95 ?
N31 C32 . 1.470(2) ?
N31 C35 . 1.472(2) ?
C32 C33 . 1.531(2) ?
C32 H32A . 0.99 ?
C32 H32B . 0.99 ?
C33 C34 . 1.543(2) ?
C33 H33A . 0.99 ?
C33 H33B . 0.99 ?
C34 C35 . 1.528(2) ?
C34 H34A . 0.99 ?
C34 H34B . 0.99 ?
C35 H35A . 0.99 ?
C35 H35B . 0.99 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 C1 C6 . . 108.75(13) ?
N2 C1 C7 . . 107.41(13) ?
C6 C1 C7 . . 108.32(13) ?
N2 C1 H1 . . 110.8 ?
C6 C1 H1 . . 110.8 ?
C7 C1 H1 . . 110.8 ?
C3 N2 C9 . . 123.70(14) ?
C3 N2 C1 . . 115.70(13) ?
C9 N2 C1 . . 120.30(13) ?
O1 C3 N2 . . 125.45(16) ?
O1 C3 C4 . . 125.43(15) ?
N2 C3 C4 . . 109.09(13) ?
N5 C4 C3 . . 108.03(13) ?
N5 C4 C8 . . 107.75(13) ?
C3 C4 C8 . . 108.12(14) ?
N5 C4 H4 . . 110.9 ?
C3 C4 H4 . . 110.9 ?
C8 C4 H4 . . 110.9 ?
C6 N5 C10 . . 124.18(15) ?
C6 N5 C4 . . 115.07(15) ?
C10 N5 C4 . . 120.13(13) ?
O2 C6 N5 . . 125.75(17) ?
O2 C6 C1 . . 124.71(15) ?
N5 C6 C1 . . 109.53(14) ?
N31 C7 C1 . . 110.05(13) ?
N31 C7 C8 . . 111.66(13) ?
C1 C7 C8 . . 106.49(13) ?
N31 C7 H7 . . 109.5 ?
C1 C7 H7 . . 109.5 ?
C8 C7 H7 . . 109.5 ?
C4 C8 C7 . . 108.91(13) ?
C4 C8 H8A . . 109.9 ?
C7 C8 H8A . . 109.9 ?
C4 C8 H8B . . 109.9 ?
C7 C8 H8B . . 109.9 ?
H8A C8 H8B . . 108.3 ?
N2 C9 C11 . . 113.03(15) ?
N2 C9 H9A . . 109.0 ?
C11 C9 H9A . . 109.0 ?
N2 C9 H9B . . 109.0 ?
C11 C9 H9B . . 109.0 ?
H9A C9 H9B . . 107.8 ?
N5 C10 C21 . . 113.96(14) ?
N5 C10 H10A . . 108.8 ?
C21 C10 H10A . . 108.8 ?
N5 C10 H10B . . 108.8 ?
C21 C10 H10B . . 108.8 ?
H10A C10 H10B . . 107.7 ?
C12 C11 C16 . . 119.16(16) ?
C12 C11 C9 . . 122.36(15) ?
C16 C11 C9 . . 118.47(16) ?
C11 C12 C13 . . 120.17(16) ?
C11 C12 H12 . . 119.9 ?
C13 C12 H12 . . 119.9 ?
C14 C13 C12 . . 120.47(19) ?
C14 C13 H13 . . 119.8 ?
C12 C13 H13 . . 119.8 ?
C13 C14 C15 . . 119.35(18) ?
C13 C14 H14 . . 120.3 ?
C15 C14 H14 . . 120.3 ?
C14 C15 C16 . . 120.34(18) ?
C14 C15 H15 . . 119.8 ?
C16 C15 H15 . . 119.8 ?
C15 C16 C11 . . 120.44(19) ?
C15 C16 H16 . . 119.8 ?
C11 C16 H16 . . 119.8 ?
C26 C21 C22 . . 118.80(17) ?
C26 C21 C10 . . 121.93(16) ?
C22 C21 C10 . . 119.21(16) ?
C23 C22 C21 . . 120.62(18) ?
C23 C22 H22 . . 119.7 ?
C21 C22 H22 . . 119.7 ?
C24 C23 C22 . . 120.19(18) ?
C24 C23 H23 . . 119.9 ?
C22 C23 H23 . . 119.9 ?
C23 C24 C25 . . 119.81(18) ?
C23 C24 H24 . . 120.1 ?
C25 C24 H24 . . 120.1 ?
C24 C25 C26 . . 120.04(19) ?
C24 C25 H25 . . 120.0 ?
C26 C25 H25 . . 120.0 ?
C21 C26 C25 . . 120.52(18) ?
C21 C26 H26 . . 119.7 ?
C25 C26 H26 . . 119.7 ?
C7 N31 C32 . . 113.22(13) ?
C7 N31 C35 . . 113.77(13) ?
C32 N31 C35 . . 103.07(13) ?
N31 C32 C33 . . 103.89(13) ?
N31 C32 H32A . . 111.0 ?
C33 C32 H32A . . 111.0 ?
N31 C32 H32B . . 111.0 ?
C33 C32 H32B . . 111.0 ?
H32A C32 H32B . . 109.0 ?
C32 C33 C34 . . 104.12(13) ?
C32 C33 H33A . . 110.9 ?
C34 C33 H33A . . 110.9 ?
C32 C33 H33B . . 110.9 ?
C34 C33 H33B . . 110.9 ?
H33A C33 H33B . . 109.0 ?
C35 C34 C33 . . 104.67(14) ?
C35 C34 H34A . . 110.8 ?
C33 C34 H34A . . 110.8 ?
C35 C34 H34B . . 110.8 ?
C33 C34 H34B . . 110.8 ?
H34A C34 H34B . . 108.9 ?
N31 C35 C34 . . 103.54(13) ?
N31 C35 H35A . . 111.1 ?
C34 C35 H35A . . 111.1 ?
N31 C35 H35B . . 111.1 ?
C34 C35 H35B . . 111.1 ?
H35A C35 H35B . . 109.0 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 N2 C3 . . . . -55.54(18) ?
C7 C1 N2 C3 . . . . 61.48(19) ?
C6 C1 N2 C9 . . . . 130.52(15) ?
C7 C1 N2 C9 . . . . -112.47(16) ?
C9 N2 C3 O1 . . . . -3.6(3) ?
C1 N2 C3 O1 . . . . -177.30(16) ?
C9 N2 C3 C4 . . . . 174.58(15) ?
C1 N2 C3 C4 . . . . 0.87(19) ?
O1 C3 C4 N5 . . . . -126.90(17) ?
N2 C3 C4 N5 . . . . 54.93(17) ?
O1 C3 C4 C8 . . . . 116.75(18) ?
N2 C3 C4 C8 . . . . -61.41(17) ?
C3 C4 N5 C6 . . . . -58.37(17) ?
C8 C4 N5 C6 . . . . 58.21(17) ?
C3 C4 N5 C10 . . . . 130.24(15) ?
C8 C4 N5 C10 . . . . -113.18(15) ?
C10 N5 C6 O2 . . . . -5.7(3) ?
C4 N5 C6 O2 . . . . -176.74(15) ?
C10 N5 C6 C1 . . . . 174.54(14) ?
C4 N5 C6 C1 . . . . 3.54(18) ?
N2 C1 C6 O2 . . . . -127.54(16) ?
C7 C1 C6 O2 . . . . 116.02(17) ?
N2 C1 C6 N5 . . . . 52.18(16) ?
C7 C1 C6 N5 . . . . -64.26(16) ?
N2 C1 C7 N31 . . . . 179.48(13) ?
C6 C1 C7 N31 . . . . -63.22(17) ?
N2 C1 C7 C8 . . . . -59.33(17) ?
C6 C1 C7 C8 . . . . 57.97(17) ?
N5 C4 C8 C7 . . . . -58.88(17) ?
C3 C4 C8 C7 . . . . 57.65(17) ?
N31 C7 C8 C4 . . . . 122.14(15) ?
C1 C7 C8 C4 . . . . 1.98(19) ?
C3 N2 C9 C11 . . . . 127.14(16) ?
C1 N2 C9 C11 . . . . -59.42(19) ?
C6 N5 C10 C21 . . . . 117.52(17) ?
C4 N5 C10 C21 . . . . -71.92(19) ?
N2 C9 C11 C12 . . . . -30.4(2) ?
N2 C9 C11 C16 . . . . 150.37(16) ?
C16 C11 C12 C13 . . . . 2.2(3) ?
C9 C11 C12 C13 . . . . -177.03(15) ?
C11 C12 C13 C14 . . . . 0.5(3) ?
C12 C13 C14 C15 . . . . -2.1(3) ?
C13 C14 C15 C16 . . . . 1.1(3) ?
C14 C15 C16 C11 . . . . 1.5(3) ?
C12 C11 C16 C15 . . . . -3.1(3) ?
C9 C11 C16 C15 . . . . 176.09(17) ?
N5 C10 C21 C26 . . . . -40.0(2) ?
N5 C10 C21 C22 . . . . 143.02(16) ?
C26 C21 C22 C23 . . . . -1.8(3) ?
C10 C21 C22 C23 . . . . 175.25(17) ?
C21 C22 C23 C24 . . . . 1.0(3) ?
C22 C23 C24 C25 . . . . 0.7(3) ?
C23 C24 C25 C26 . . . . -1.5(3) ?
C22 C21 C26 C25 . . . . 1.0(3) ?
C10 C21 C26 C25 . . . . -175.94(17) ?
C24 C25 C26 C21 . . . . 0.6(3) ?
C1 C7 N31 C32 . . . . -177.92(14) ?
C8 C7 N31 C32 . . . . 64.03(18) ?
C1 C7 N31 C35 . . . . -60.67(18) ?
C8 C7 N31 C35 . . . . -178.71(14) ?
C7 N31 C32 C33 . . . . 167.40(14) ?
C35 N31 C32 C33 . . . . 44.04(18) ?
N31 C32 C33 C34 . . . . -26.33(19) ?
C32 C33 C34 C35 . . . . -0.3(2) ?
C7 N31 C35 C34 . . . . -167.09(14) ?
C32 N31 C35 C34 . . . . -44.10(17) ?
C33 C34 C35 N31 . . . . 26.73(19) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C4 H4 O1 4_565 1.00 2.39 3.121(2) 129.1 ?
C9 H9B O2 2_764 0.99 2.38 3.232(2) 144.3 ?

####################################################################### 
# 
# 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_dan8093
_database_code_depnum_ccdc_archive 'CCDC 1546597'
_audit_update_record             
;
2017-04-27 deposited with the CCDC.
2017-07-18 downloaded from the CCDC.
;

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H27 Cl4 N3 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         555.30

_chemical_melting_point          ?

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

_cell_length_a                   24.6806(6)
_cell_length_b                   6.2455(2)
_cell_length_c                   16.1174(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.5410(10)
_cell_angle_gamma                90
_cell_volume                     2479.64(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9893
_cell_measurement_theta_min      3.5884
_cell_measurement_theta_max      68.2582
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.228
_exptl_crystal_size_mid          0.051
_exptl_crystal_size_min          0.015
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1152

_exptl_absorpt_coefficient_mu    4.588
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/2, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.68
_exptl_absorpt_correction_T_max  0.93

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            31737
_diffrn_reflns_av_R_equivalents  0.0860
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_theta_min         3.59
_diffrn_reflns_theta_max         68.36
_diffrn_reflns_theta_full        68.36
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19

_refine_special_details          
;
;

_reflns_number_total             4563
_reflns_number_gt                3427
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_gt          0.1299
_refine_ls_wR_factor_ref         0.1425
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_number_reflns         4563
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0644P)²+3.0587P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.618
_refine_diff_density_min         -0.443
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
;
APEX2 v.2014.1-1 (Bruker AXS Inc., 2014)

;
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.57384(4) 0.58037(16) 0.31174(5) 0.0407(2) Uani d . . . 1 . .
Cl Cl2 0.52820(3) 0.12464(15) 0.35622(5) 0.0350(2) Uani d . . . 1 . .
Cl Cl3 0.93539(4) 1.12929(18) 1.03645(9) 0.0612(4) Uani d . . . 1 . .
Cl Cl4 0.96694(4) 0.67149(19) 1.10688(8) 0.0581(3) Uani d . . . 1 . .
N N2 0.68819(10) 0.7604(4) 0.73645(17) 0.0231(6) Uani d . . . 1 . .
N N5 0.71060(11) 0.9542(4) 0.89444(16) 0.0243(6) Uani d . . . 1 . .
N N31 0.83114(11) 0.7983(5) 0.82450(18) 0.0287(6) Uani d . . . 1 . .
O O1 0.68303(9) 0.4453(4) 0.66718(14) 0.0269(5) Uani d . . . 1 . .
O O2 0.72123(10) 1.2536(4) 0.97421(16) 0.0355(6) Uani d . . . 1 . .
C C1 0.73483(13) 0.6966(5) 0.7923(2) 0.0262(7) Uani d . . . 1 . .
H H1 0.7443 0.5435 0.7822 0.031 Uiso calc U . R 1 . .
C C3 0.66641(13) 0.9758(5) 0.7553(2) 0.0267(7) Uani d . . . 1 . .
H H3A 0.6306 0.9629 0.7795 0.032 Uiso calc U . R 1 . .
H H3B 0.662 1.063 0.704 0.032 Uiso calc U . R 1 . .
C C4 0.70728(13) 1.0787(5) 0.81704(19) 0.0242(7) Uani d . . . 1 . .
H H4 0.6961 1.2291 0.8286 0.029 Uiso calc U . R 1 . .
C C6 0.72039(14) 0.7263(5) 0.8816(2) 0.0276(7) Uani d . . . 1 . .
H H6A 0.6875 0.6426 0.8923 0.033 Uiso calc U . R 1 . .
H H6B 0.7505 0.676 0.9201 0.033 Uiso calc U . R 1 . .
C C7 0.78228(13) 0.8427(5) 0.7709(2) 0.0252(7) Uani d . . . 1 . .
H H7 0.7905 0.8192 0.7116 0.03 Uiso calc U . R 1 . .
C C8 0.76372(13) 1.0775(5) 0.7820(2) 0.0251(7) Uani d . . . 1 . .
H H8A 0.7899 1.1534 0.8205 0.03 Uiso calc U . R 1 . .
H H8B 0.7623 1.1523 0.7278 0.03 Uiso calc U . R 1 . .
C C9 0.66575(12) 0.6261(5) 0.67839(19) 0.0206(7) Uani d . . . 1 . .
C C10 0.72040(13) 1.0571(6) 0.9684(2) 0.0276(7) Uani d . . . 1 . .
C C11 0.61689(12) 0.7168(5) 0.6269(2) 0.0238(7) Uani d . . . 1 . .
H H11A 0.5876 0.748 0.6644 0.029 Uiso calc U . R 1 . .
H H11B 0.6275 0.8536 0.6015 0.029 Uiso calc U . R 1 . .
C C12 0.59530(12) 0.5688(5) 0.55937(19) 0.0225(7) Uani d . . . 1 . .
C C13 0.59459(12) 0.6313(5) 0.4767(2) 0.0252(7) Uani d . . . 1 . .
H H13 0.6084 0.7678 0.4629 0.03 Uiso calc U . R 1 . .
C C14 0.57396(13) 0.4969(6) 0.4142(2) 0.0270(7) Uani d . . . 1 . .
C C15 0.55392(12) 0.2963(6) 0.4332(2) 0.0259(7) Uani d . . . 1 . .
C C16 0.55456(13) 0.2329(6) 0.5155(2) 0.0290(8) Uani d . . . 1 . .
H H16 0.5409 0.0959 0.529 0.035 Uiso calc U . R 1 . .
C C17 0.57488(13) 0.3668(6) 0.5780(2) 0.0289(8) Uani d . . . 1 . .
H H17 0.575 0.3213 0.6343 0.035 Uiso calc U . R 1 . .
C C21 0.73135(13) 0.9170(6) 1.0437(2) 0.0322(8) Uani d . . . 1 . .
H H21A 0.7086 0.7867 1.0379 0.039 Uiso calc U . R 1 . .
H H21B 0.7209 0.995 1.0938 0.039 Uiso calc U . R 1 . .
C C22 0.79125(13) 0.8516(6) 1.0554(2) 0.0292(8) Uani d . . . 1 . .
C C23 0.83158(14) 0.9976(6) 1.0416(2) 0.0334(8) Uani d . . . 1 . .
H H23 0.8222 1.1369 1.0218 0.04 Uiso calc U . R 1 . .
C C24 0.88530(15) 0.9433(7) 1.0561(2) 0.0379(9) Uani d . . . 1 . .
C C25 0.89951(14) 0.7419(7) 1.0856(2) 0.0394(9) Uani d . . . 1 . .
C C26 0.85956(15) 0.5941(7) 1.0987(2) 0.0409(9) Uani d . . . 1 . .
H H26 0.8692 0.4553 1.1186 0.049 Uiso calc U . R 1 . .
C C27 0.80512(15) 0.6468(6) 1.0830(2) 0.0352(8) Uani d . . . 1 . .
H H27 0.7777 0.5436 1.091 0.042 Uiso calc U . R 1 . .
C C32 0.87854(15) 0.9215(8) 0.7987(3) 0.0454(10) Uani d . . . 1 . .
H H32A 0.8801 1.0639 0.8257 0.055 Uiso calc U . R 1 . .
H H32B 0.8765 0.9416 0.7376 0.055 Uiso calc U . R 1 . .
C C33 0.92721(17) 0.7906(8) 0.8260(5) 0.0802(19) Uani d . . . 1 . .
H H33A 0.9512 0.7729 0.7795 0.096 Uiso calc U . R 1 . .
H H33B 0.9481 0.8627 0.8725 0.096 Uiso calc U . R 1 . .
C C34 0.90767(16) 0.5780(8) 0.8534(3) 0.0511(11) Uani d . . . 1 . .
H H34A 0.9126 0.5635 0.9145 0.061 Uiso calc U . R 1 . .
H H34B 0.9276 0.4609 0.8272 0.061 Uiso calc U . R 1 . .
C C35 0.84796(14) 0.5723(6) 0.8251(3) 0.0368(9) Uani d . . . 1 . .
H H35A 0.8426 0.5089 0.7689 0.044 Uiso calc U . R 1 . .
H H35B 0.8271 0.488 0.8641 0.044 Uiso calc U . R 1 . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C14 . 1.731(3) ?
Cl2 C15 . 1.731(3) ?
Cl3 C24 . 1.740(4) ?
Cl4 C25 . 1.735(4) ?
N2 C9 . 1.350(4) ?
N2 C1 . 1.472(4) ?
N2 C3 . 1.487(4) ?
N5 C10 . 1.362(4) ?
N5 C6 . 1.461(4) ?
N5 C4 . 1.468(4) ?
N31 C7 . 1.466(4) ?
N31 C35 . 1.471(5) ?
N31 C32 . 1.481(5) ?
O1 C9 . 1.225(4) ?
O2 C10 . 1.231(4) ?
C1 C6 . 1.515(5) ?
C1 C7 . 1.540(5) ?
C1 H1 . 1.0 ?
C3 C4 . 1.515(5) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 C8 . 1.535(4) ?
C4 H4 . 1.0 ?
C6 H6A . 0.99 ?
C6 H6B . 0.99 ?
C7 C8 . 1.550(5) ?
C7 H7 . 1.0 ?
C8 H8A . 0.99 ?
C8 H8B . 0.99 ?
C9 C11 . 1.530(4) ?
C10 C21 . 1.507(5) ?
C11 C12 . 1.501(4) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
C12 C13 . 1.387(5) ?
C12 C17 . 1.398(5) ?
C13 C14 . 1.385(5) ?
C13 H13 . 0.95 ?
C14 C15 . 1.388(5) ?
C15 C16 . 1.383(5) ?
C16 C17 . 1.380(5) ?
C16 H16 . 0.95 ?
C17 H17 . 0.95 ?
C21 C22 . 1.534(5) ?
C21 H21A . 0.99 ?
C21 H21B . 0.99 ?
C22 C23 . 1.379(5) ?
C22 C27 . 1.390(5) ?
C23 C24 . 1.374(5) ?
C23 H23 . 0.95 ?
C24 C25 . 1.383(6) ?
C25 C26 . 1.376(6) ?
C26 C27 . 1.391(5) ?
C26 H26 . 0.95 ?
C27 H27 . 0.95 ?
C32 C33 . 1.497(6) ?
C32 H32A . 0.99 ?
C32 H32B . 0.99 ?
C33 C34 . 1.489(7) ?
C33 H33A . 0.99 ?
C33 H33B . 0.99 ?
C34 C35 . 1.516(5) ?
C34 H34A . 0.99 ?
C34 H34B . 0.99 ?
C35 H35A . 0.99 ?
C35 H35B . 0.99 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 N2 C1 . . 121.8(3) ?
C9 N2 C3 . . 124.5(3) ?
C1 N2 C3 . . 113.5(3) ?
C10 N5 C6 . . 124.2(3) ?
C10 N5 C4 . . 119.4(3) ?
C6 N5 C4 . . 113.4(3) ?
C7 N31 C35 . . 114.0(3) ?
C7 N31 C32 . . 111.8(3) ?
C35 N31 C32 . . 105.8(3) ?
N2 C1 C6 . . 109.1(3) ?
N2 C1 C7 . . 106.2(3) ?
C6 C1 C7 . . 111.5(3) ?
N2 C1 H1 . . 110.0 ?
C6 C1 H1 . . 110.0 ?
C7 C1 H1 . . 110.0 ?
N2 C3 C4 . . 106.5(3) ?
N2 C3 H3A . . 110.4 ?
C4 C3 H3A . . 110.4 ?
N2 C3 H3B . . 110.4 ?
C4 C3 H3B . . 110.4 ?
H3A C3 H3B . . 108.6 ?
N5 C4 C3 . . 109.5(3) ?
N5 C4 C8 . . 107.8(3) ?
C3 C4 C8 . . 109.8(3) ?
N5 C4 H4 . . 109.9 ?
C3 C4 H4 . . 109.9 ?
C8 C4 H4 . . 109.9 ?
N5 C6 C1 . . 107.7(3) ?
N5 C6 H6A . . 110.2 ?
C1 C6 H6A . . 110.2 ?
N5 C6 H6B . . 110.2 ?
C1 C6 H6B . . 110.2 ?
H6A C6 H6B . . 108.5 ?
N31 C7 C1 . . 111.4(3) ?
N31 C7 C8 . . 110.4(3) ?
C1 C7 C8 . . 107.5(3) ?
N31 C7 H7 . . 109.2 ?
C1 C7 H7 . . 109.2 ?
C8 C7 H7 . . 109.2 ?
C4 C8 C7 . . 109.2(3) ?
C4 C8 H8A . . 109.8 ?
C7 C8 H8A . . 109.8 ?
C4 C8 H8B . . 109.8 ?
C7 C8 H8B . . 109.8 ?
H8A C8 H8B . . 108.3 ?
O1 C9 N2 . . 122.9(3) ?
O1 C9 C11 . . 122.1(3) ?
N2 C9 C11 . . 115.0(3) ?
O2 C10 N5 . . 122.6(3) ?
O2 C10 C21 . . 121.0(3) ?
N5 C10 C21 . . 116.4(3) ?
C12 C11 C9 . . 113.5(3) ?
C12 C11 H11A . . 108.9 ?
C9 C11 H11A . . 108.9 ?
C12 C11 H11B . . 108.9 ?
C9 C11 H11B . . 108.9 ?
H11A C11 H11B . . 107.7 ?
C13 C12 C17 . . 118.5(3) ?
C13 C12 C11 . . 120.4(3) ?
C17 C12 C11 . . 121.1(3) ?
C14 C13 C12 . . 120.7(3) ?
C14 C13 H13 . . 119.6 ?
C12 C13 H13 . . 119.6 ?
C13 C14 C15 . . 120.4(3) ?
C13 C14 Cl1 . . 119.4(3) ?
C15 C14 Cl1 . . 120.2(3) ?
C16 C15 C14 . . 119.2(3) ?
C16 C15 Cl2 . . 119.5(3) ?
C14 C15 Cl2 . . 121.4(3) ?
C17 C16 C15 . . 120.6(3) ?
C17 C16 H16 . . 119.7 ?
C15 C16 H16 . . 119.7 ?
C16 C17 C12 . . 120.6(3) ?
C16 C17 H17 . . 119.7 ?
C12 C17 H17 . . 119.7 ?
C10 C21 C22 . . 112.2(3) ?
C10 C21 H21A . . 109.2 ?
C22 C21 H21A . . 109.2 ?
C10 C21 H21B . . 109.2 ?
C22 C21 H21B . . 109.2 ?
H21A C21 H21B . . 107.9 ?
C23 C22 C27 . . 119.7(3) ?
C23 C22 C21 . . 120.2(3) ?
C27 C22 C21 . . 120.1(3) ?
C24 C23 C22 . . 120.5(4) ?
C24 C23 H23 . . 119.7 ?
C22 C23 H23 . . 119.7 ?
C23 C24 C25 . . 120.3(4) ?
C23 C24 Cl3 . . 119.6(3) ?
C25 C24 Cl3 . . 120.1(3) ?
C26 C25 C24 . . 119.6(3) ?
C26 C25 Cl4 . . 119.2(3) ?
C24 C25 Cl4 . . 121.2(3) ?
C25 C26 C27 . . 120.5(4) ?
C25 C26 H26 . . 119.8 ?
C27 C26 H26 . . 119.8 ?
C22 C27 C26 . . 119.4(4) ?
C22 C27 H27 . . 120.3 ?
C26 C27 H27 . . 120.3 ?
N31 C32 C33 . . 105.5(4) ?
N31 C32 H32A . . 110.6 ?
C33 C32 H32A . . 110.6 ?
N31 C32 H32B . . 110.6 ?
C33 C32 H32B . . 110.6 ?
H32A C32 H32B . . 108.8 ?
C34 C33 C32 . . 107.8(4) ?
C34 C33 H33A . . 110.1 ?
C32 C33 H33A . . 110.1 ?
C34 C33 H33B . . 110.1 ?
C32 C33 H33B . . 110.1 ?
H33A C33 H33B . . 108.5 ?
C33 C34 C35 . . 105.0(4) ?
C33 C34 H34A . . 110.8 ?
C35 C34 H34A . . 110.8 ?
C33 C34 H34B . . 110.8 ?
C35 C34 H34B . . 110.8 ?
H34A C34 H34B . . 108.8 ?
N31 C35 C34 . . 104.4(3) ?
N31 C35 H35A . . 110.9 ?
C34 C35 H35A . . 110.9 ?
N31 C35 H35B . . 110.9 ?
C34 C35 H35B . . 110.9 ?
H35A C35 H35B . . 108.9 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9 N2 C1 C6 . . . . -124.2(3) ?
C3 N2 C1 C6 . . . . 51.1(3) ?
C9 N2 C1 C7 . . . . 115.5(3) ?
C3 N2 C1 C7 . . . . -69.2(3) ?
C9 N2 C3 C4 . . . . -174.0(3) ?
C1 N2 C3 C4 . . . . 10.9(4) ?
C10 N5 C4 C3 . . . . -146.6(3) ?
C6 N5 C4 C3 . . . . 52.3(3) ?
C10 N5 C4 C8 . . . . 94.0(3) ?
C6 N5 C4 C8 . . . . -67.1(3) ?
N2 C3 C4 N5 . . . . -63.6(3) ?
N2 C3 C4 C8 . . . . 54.6(3) ?
C10 N5 C6 C1 . . . . -149.3(3) ?
C4 N5 C6 C1 . . . . 10.7(4) ?
N2 C1 C6 N5 . . . . -63.2(3) ?
C7 C1 C6 N5 . . . . 53.9(3) ?
C35 N31 C7 C1 . . . . 54.0(4) ?
C32 N31 C7 C1 . . . . 173.9(3) ?
C35 N31 C7 C8 . . . . 173.3(3) ?
C32 N31 C7 C8 . . . . -66.7(4) ?
N2 C1 C7 N31 . . . . 178.4(3) ?
C6 C1 C7 N31 . . . . 59.7(4) ?
N2 C1 C7 C8 . . . . 57.3(3) ?
C6 C1 C7 C8 . . . . -61.5(3) ?
N5 C4 C8 C7 . . . . 55.9(3) ?
C3 C4 C8 C7 . . . . -63.4(3) ?
N31 C7 C8 C4 . . . . -117.0(3) ?
C1 C7 C8 C4 . . . . 4.8(4) ?
C1 N2 C9 O1 . . . . -1.4(5) ?
C3 N2 C9 O1 . . . . -176.2(3) ?
C1 N2 C9 C11 . . . . 178.8(3) ?
C3 N2 C9 C11 . . . . 4.0(4) ?
C6 N5 C10 O2 . . . . 166.5(3) ?
C4 N5 C10 O2 . . . . 7.6(5) ?
C6 N5 C10 C21 . . . . -12.4(4) ?
C4 N5 C10 C21 . . . . -171.4(3) ?
O1 C9 C11 C12 . . . . -3.6(4) ?
N2 C9 C11 C12 . . . . 176.2(3) ?
C9 C11 C12 C13 . . . . -119.2(3) ?
C9 C11 C12 C17 . . . . 61.6(4) ?
C17 C12 C13 C14 . . . . 0.2(5) ?
C11 C12 C13 C14 . . . . -179.0(3) ?
C12 C13 C14 C15 . . . . -0.4(5) ?
C12 C13 C14 Cl1 . . . . -179.9(2) ?
C13 C14 C15 C16 . . . . 0.3(5) ?
Cl1 C14 C15 C16 . . . . 179.8(3) ?
C13 C14 C15 Cl2 . . . . -179.7(3) ?
Cl1 C14 C15 Cl2 . . . . -0.2(4) ?
C14 C15 C16 C17 . . . . -0.1(5) ?
Cl2 C15 C16 C17 . . . . 180.0(3) ?
C15 C16 C17 C12 . . . . -0.2(5) ?
C13 C12 C17 C16 . . . . 0.1(5) ?
C11 C12 C17 C16 . . . . 179.3(3) ?
O2 C10 C21 C22 . . . . -93.7(4) ?
N5 C10 C21 C22 . . . . 85.3(4) ?
C10 C21 C22 C23 . . . . 40.4(5) ?
C10 C21 C22 C27 . . . . -141.9(3) ?
C27 C22 C23 C24 . . . . -1.0(5) ?
C21 C22 C23 C24 . . . . 176.6(3) ?
C22 C23 C24 C25 . . . . -0.7(6) ?
C22 C23 C24 Cl3 . . . . 178.9(3) ?
C23 C24 C25 C26 . . . . 1.4(6) ?
Cl3 C24 C25 C26 . . . . -178.2(3) ?
C23 C24 C25 Cl4 . . . . -178.4(3) ?
Cl3 C24 C25 Cl4 . . . . 2.0(5) ?
C24 C25 C26 C27 . . . . -0.5(6) ?
Cl4 C25 C26 C27 . . . . 179.4(3) ?
C23 C22 C27 C26 . . . . 2.0(5) ?
C21 C22 C27 C26 . . . . -175.7(3) ?
C25 C26 C27 C22 . . . . -1.2(6) ?
C7 N31 C32 C33 . . . . -152.5(4) ?
C35 N31 C32 C33 . . . . -27.9(5) ?
N31 C32 C33 C34 . . . . 9.9(6) ?
C32 C33 C34 C35 . . . . 11.1(6) ?
C7 N31 C35 C34 . . . . 158.1(3) ?
C32 N31 C35 C34 . . . . 34.8(4) ?
C33 C34 C35 N31 . . . . -28.1(5) ?

