# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2015

####################################################################### 
# 
# 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_s1922lm
_database_code_depnum_ccdc_archive 'CCDC 1030119'
_audit_update_record             
;
2014-10-20 deposited with the CCDC.
2014-12-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 '6b.Br' 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H46 N5 O2, Br, H2 O'
_chemical_formula_sum            'C29 H48 Br N5 O3'
_chemical_formula_weight         594.63

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0979(4)
_cell_length_b                   10.1206(6)
_cell_length_c                   20.3102(12)
_cell_angle_alpha                78.159(4)
_cell_angle_beta                 88.100(3)
_cell_angle_gamma                69.662(3)
_cell_volume                     1526.23(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5698
_cell_measurement_theta_min      2.05
_cell_measurement_theta_max      28.36

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    1.384
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7709
_exptl_absorpt_correction_T_max  0.8714
_exptl_absorpt_process_details   'Blessing, 1995'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  Triumph
_diffrn_measurement_device_type  'Bruker Kappa APEXII Duo'
_diffrn_measurement_method       'Omega- und Phi-Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            26683
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_sigmaI/netI    0.0642
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         28.36
_reflns_number_total             7547
_reflns_number_gt                5698
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEXII Software Suite, 2008'
_computing_cell_refinement       'Bruker APEXII Software Suite, 2008'
_computing_data_reduction        'Bruker APEXII Software Suite, 2008'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL-plus, XP (Sheldrick, 1991)'
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0403P)²+0.3747P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7547
_refine_ls_number_parameters     357
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0413
_refine_ls_wR_factor_ref         0.0911
_refine_ls_wR_factor_gt          0.0856
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.99843(3) -0.80734(3) 0.105854(12) 0.02033(8) Uani 1 1 d . . .
O1 O 1.10390(18) -0.38439(15) 0.18960(7) 0.0154(3) Uani 1 1 d . . .
N1 N 0.7155(2) -0.01972(19) 0.35404(9) 0.0131(4) Uani 1 1 d . . .
C1 C 1.4595(2) -0.7779(2) 0.00457(11) 0.0112(4) Uani 1 1 d . . .
O2 O 0.27398(18) 0.43692(15) 0.51122(7) 0.0165(3) Uani 1 1 d . . .
N2 N 0.6795(2) 0.11458(18) 0.33405(9) 0.0121(4) Uani 1 1 d . . .
C2 C 1.3736(3) -0.7109(3) -0.11620(11) 0.0204(5) Uani 1 1 d . . .
H2A H 1.4776 -0.7962 -0.1178 0.031 Uiso 1 1 calc R . .
H2B H 1.3911 -0.6256 -0.1437 0.031 Uiso 1 1 calc R . .
H2C H 1.2696 -0.7230 -0.1338 0.031 Uiso 1 1 calc R . .
N3 N 1.4006(2) -0.80626(18) 0.06604(8) 0.0113(4) Uani 1 1 d . . .
H3 H 1.2934 -0.8096 0.0689 0.030(7) Uiso 1 1 calc R . .
C3 C 1.1734(3) -0.5942(2) -0.03514(12) 0.0210(5) Uani 1 1 d . . .
H3A H 1.0868 -0.6424 -0.0338 0.032 Uiso 1 1 calc R . .
H3B H 1.1398 -0.5087 -0.0717 0.032 Uiso 1 1 calc R . .
H3C H 1.1768 -0.5653 0.0078 0.032 Uiso 1 1 calc R . .
N4 N 1.3473(2) -0.69295(18) -0.04668(8) 0.0128(4) Uani 1 1 d . . .
C4 C 1.7422(3) -0.9779(2) 0.02961(12) 0.0176(5) Uani 1 1 d . . .
H4A H 1.6669 -1.0291 0.0527 0.026 Uiso 1 1 calc R . .
H4B H 1.8204 -0.9685 0.0628 0.026 Uiso 1 1 calc R . .
H4C H 1.8130 -1.0321 -0.0026 0.026 Uiso 1 1 calc R . .
N5 N 1.6318(2) -0.83438(19) -0.00638(9) 0.0140(4) Uani 1 1 d . . .
C5 C 1.7226(3) -0.7571(3) -0.05403(12) 0.0250(6) Uani 1 1 d . . .
H5A H 1.6431 -0.6580 -0.0706 0.038 Uiso 1 1 calc R . .
H5B H 1.7586 -0.8054 -0.0920 0.038 Uiso 1 1 calc R . .
H5C H 1.8271 -0.7559 -0.0315 0.038 Uiso 1 1 calc R . .
C6 C 1.5007(2) -0.8323(2) 0.12946(10) 0.0125(4) Uani 1 1 d . . .
H6A H 1.5959 -0.7913 0.1209 0.015 Uiso 1 1 calc R . .
H6B H 1.5559 -0.9373 0.1469 0.015 Uiso 1 1 calc R . .
C7 C 1.3805(3) -0.7640(2) 0.18190(10) 0.0126(4) Uani 1 1 d . . .
H7A H 1.2833 -0.8030 0.1887 0.015 Uiso 1 1 calc R . .
H7B H 1.4486 -0.7920 0.2252 0.015 Uiso 1 1 calc R . .
C8 C 1.3018(3) -0.6002(2) 0.16279(11) 0.0139(4) Uani 1 1 d . . .
H8A H 1.3975 -0.5600 0.1612 0.017 Uiso 1 1 calc R . .
H8B H 1.2442 -0.5712 0.1173 0.017 Uiso 1 1 calc R . .
C9 C 1.1676(3) -0.5382(2) 0.21257(11) 0.0136(4) Uani 1 1 d . . .
H9A H 1.0693 -0.5754 0.2140 0.016 Uiso 1 1 calc R . .
H9B H 1.2234 -0.5650 0.2583 0.016 Uiso 1 1 calc R . .
C10 C 0.9663(2) -0.1524(2) 0.20897(11) 0.0134(4) Uani 1 1 d . . .
H10 H 1.0053 -0.1176 0.1665 0.016 Uiso 1 1 calc R . .
C11 C 0.8718(2) -0.0565(2) 0.24717(11) 0.0124(4) Uani 1 1 d . . .
H11 H 0.8458 0.0439 0.2312 0.015 Uiso 1 1 calc R . .
C12 C 0.8137(2) -0.1074(2) 0.30977(10) 0.0112(4) Uani 1 1 d . . .
C13 C 0.8511(3) -0.2547(2) 0.33162(11) 0.0142(5) Uani 1 1 d . . .
H13 H 0.8103 -0.2893 0.3737 0.017 Uiso 1 1 calc R . .
C14 C 0.9465(3) -0.3518(2) 0.29332(11) 0.0139(4) Uani 1 1 d . . .
H14 H 0.9710 -0.4521 0.3089 0.017 Uiso 1 1 calc R . .
C15 C 1.0061(2) -0.3004(2) 0.23161(11) 0.0124(4) Uani 1 1 d . . .
C16 C 0.5797(2) 0.1958(2) 0.38058(11) 0.0120(4) Uani 1 1 d . . .
C17 C 0.5042(2) 0.3443(2) 0.35839(11) 0.0136(4) Uani 1 1 d . . .
H17 H 0.5242 0.3874 0.3142 0.016 Uiso 1 1 calc R . .
C18 C 0.3999(3) 0.4304(2) 0.40003(11) 0.0150(5) Uani 1 1 d . . .
H18 H 0.3473 0.5315 0.3843 0.018 Uiso 1 1 calc R . .
C19 C 0.3738(2) 0.3661(2) 0.46527(11) 0.0122(4) Uani 1 1 d . . .
C20 C 0.4538(3) 0.2190(2) 0.48822(11) 0.0139(4) Uani 1 1 d . . .
H20 H 0.4382 0.1763 0.5331 0.017 Uiso 1 1 calc R . .
C21 C 0.5556(2) 0.1342(2) 0.44667(11) 0.0131(4) Uani 1 1 d . . .
H21 H 0.6097 0.0334 0.4629 0.016 Uiso 1 1 calc R . .
C22 C 0.1921(3) 0.5912(2) 0.49449(11) 0.0145(5) Uani 1 1 d . . .
H22A H 0.1094 0.6210 0.4550 0.017 Uiso 1 1 calc R . .
H22B H 0.2821 0.6374 0.4842 0.017 Uiso 1 1 calc R . .
C23 C 0.0946(3) 0.6322(2) 0.55611(11) 0.0143(5) Uani 1 1 d . . .
H23A H 0.1789 0.5940 0.5955 0.017 Uiso 1 1 calc R . .
H23B H 0.0045 0.5858 0.5647 0.017 Uiso 1 1 calc R . .
C24 C 0.0052(3) 0.7932(2) 0.55001(11) 0.0138(4) Uani 1 1 d . . .
H24A H -0.0826 0.8317 0.5118 0.017 Uiso 1 1 calc R . .
H24B H 0.0941 0.8407 0.5405 0.017 Uiso 1 1 calc R . .
C25 C -0.0867(3) 0.8285(2) 0.61437(11) 0.0139(5) Uani 1 1 d . . .
H25A H -0.1833 0.7888 0.6211 0.017 Uiso 1 1 calc R . .
H25B H -0.0013 0.7802 0.6531 0.017 Uiso 1 1 calc R . .
C26 C -0.1623(3) 0.9886(2) 0.61376(11) 0.0133(4) Uani 1 1 d . . .
H26A H -0.2448 1.0374 0.5742 0.016 Uiso 1 1 calc R . .
H26B H -0.0651 1.0277 0.6087 0.016 Uiso 1 1 calc R . .
C27 C -0.2591(3) 1.0231(2) 0.67728(11) 0.0134(4) Uani 1 1 d . . .
H27A H -0.3587 0.9870 0.6816 0.016 Uiso 1 1 calc R . .
H27B H -0.1777 0.9718 0.7170 0.016 Uiso 1 1 calc R . .
C28 C -0.3292(3) 1.1832(2) 0.67718(11) 0.0172(5) Uani 1 1 d . . .
H28A H -0.4150 1.2341 0.6387 0.021 Uiso 1 1 calc R . .
H28B H -0.2305 1.2204 0.6708 0.021 Uiso 1 1 calc R . .
C29 C -0.4183(3) 1.2162(3) 0.74222(12) 0.0244(5) Uani 1 1 d . . .
H29A H -0.5205 1.1848 0.7475 0.037 Uiso 1 1 calc R . .
H29B H -0.4570 1.3200 0.7404 0.037 Uiso 1 1 calc R . .
H29C H -0.3345 1.1648 0.7806 0.037 Uiso 1 1 calc R . .
O1W O 1.7476(3) -0.6473(2) 0.22019(11) 0.0343(5) Uani 1 1 d . . .
H1W1 H 1.810(4) -0.681(3) 0.1928(15) 0.039(9) Uiso 1 1 d . . .
H2W1 H 1.748(4) -0.726(4) 0.2508(18) 0.062(11) Uiso 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 C15 1.365(2) . ?
O1 C9 1.437(2) . ?
N1 N2 1.266(2) . ?
N1 C12 1.421(3) . ?
C1 N3 1.333(3) . ?
C1 N4 1.342(3) . ?
C1 N5 1.342(2) . ?
O2 C19 1.363(2) . ?
O2 C22 1.439(2) . ?
N2 C16 1.424(3) . ?
C2 N4 1.460(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
N3 C6 1.472(3) . ?
N3 H3 0.8800 . ?
C3 N4 1.460(2) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 N5 1.466(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
N5 C5 1.460(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.525(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.524(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.520(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.372(3) . ?
C10 C15 1.396(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.401(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.391(3) . ?
C13 C14 1.384(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.393(3) . ?
C14 H14 0.9500 . ?
C16 C17 1.392(3) . ?
C16 C21 1.397(3) . ?
C17 C18 1.389(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.395(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.386(3) . ?
C20 C21 1.373(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.510(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.516(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.527(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.517(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.526(3) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.519(3) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.526(3) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
O1W H1W1 0.79(3) . ?
O1W H2W1 0.90(4) . ?

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
C15 O1 C9 118.69(16) . . ?
N2 N1 C12 115.91(17) . . ?
N3 C1 N4 120.36(17) . . ?
N3 C1 N5 120.06(18) . . ?
N4 C1 N5 119.58(18) . . ?
C19 O2 C22 119.67(16) . . ?
N1 N2 C16 112.88(17) . . ?
N4 C2 H2A 109.5 . . ?
N4 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N4 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 N3 C6 125.14(16) . . ?
C1 N3 H3 117.4 . . ?
C6 N3 H3 117.4 . . ?
N4 C3 H3A 109.5 . . ?
N4 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N4 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 N4 C2 122.97(17) . . ?
C1 N4 C3 121.64(17) . . ?
C2 N4 C3 114.38(17) . . ?
N5 C4 H4A 109.5 . . ?
N5 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N5 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C1 N5 C5 122.60(18) . . ?
C1 N5 C4 121.92(17) . . ?
C5 N5 C4 115.48(16) . . ?
N5 C5 H5A 109.5 . . ?
N5 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N5 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N3 C6 C7 110.77(15) . . ?
N3 C6 H6A 109.5 . . ?
C7 C6 H6A 109.5 . . ?
N3 C6 H6B 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C8 C7 C6 113.76(17) . . ?
C8 C7 H7A 108.8 . . ?
C6 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
C6 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C9 C8 C7 111.86(17) . . ?
C9 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
O1 C9 C8 106.72(16) . . ?
O1 C9 H9A 110.4 . . ?
C8 C9 H9A 110.4 . . ?
O1 C9 H9B 110.4 . . ?
C8 C9 H9B 110.4 . . ?
H9A C9 H9B 108.6 . . ?
C11 C10 C15 120.97(19) . . ?
C11 C10 H10 119.5 . . ?
C15 C10 H10 119.5 . . ?
C10 C11 C12 119.7(2) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C13 C12 C11 119.16(19) . . ?
C13 C12 N1 115.67(18) . . ?
C11 C12 N1 125.17(19) . . ?
C14 C13 C12 121.39(19) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C15 119.0(2) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
O1 C15 C14 124.99(19) . . ?
O1 C15 C10 115.26(18) . . ?
C14 C15 C10 119.75(19) . . ?
C17 C16 C21 119.05(19) . . ?
C17 C16 N2 117.50(18) . . ?
C21 C16 N2 123.45(18) . . ?
C18 C17 C16 120.9(2) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C19 119.04(19) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
O2 C19 C20 114.56(18) . . ?
O2 C19 C18 125.34(19) . . ?
C20 C19 C18 120.09(19) . . ?
C21 C20 C19 120.6(2) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C16 120.20(19) . . ?
C20 C21 H21 119.9 . . ?
C16 C21 H21 119.9 . . ?
O2 C22 C23 105.35(17) . . ?
O2 C22 H22A 110.7 . . ?
C23 C22 H22A 110.7 . . ?
O2 C22 H22B 110.7 . . ?
C23 C22 H22B 110.7 . . ?
H22A C22 H22B 108.8 . . ?
C22 C23 C24 113.76(18) . . ?
C22 C23 H23A 108.8 . . ?
C24 C23 H23A 108.8 . . ?
C22 C23 H23B 108.8 . . ?
C24 C23 H23B 108.8 . . ?
H23A C23 H23B 107.7 . . ?
C23 C24 C25 111.47(18) . . ?
C23 C24 H24A 109.3 . . ?
C25 C24 H24A 109.3 . . ?
C23 C24 H24B 109.3 . . ?
C25 C24 H24B 109.3 . . ?
H24A C24 H24B 108.0 . . ?
C26 C25 C24 113.65(17) . . ?
C26 C25 H25A 108.8 . . ?
C24 C25 H25A 108.8 . . ?
C26 C25 H25B 108.8 . . ?
C24 C25 H25B 108.8 . . ?
H25A C25 H25B 107.7 . . ?
C25 C26 C27 113.30(17) . . ?
C25 C26 H26A 108.9 . . ?
C27 C26 H26A 108.9 . . ?
C25 C26 H26B 108.9 . . ?
C27 C26 H26B 108.9 . . ?
H26A C26 H26B 107.7 . . ?
C28 C27 C26 112.93(18) . . ?
C28 C27 H27A 109.0 . . ?
C26 C27 H27A 109.0 . . ?
C28 C27 H27B 109.0 . . ?
C26 C27 H27B 109.0 . . ?
H27A C27 H27B 107.8 . . ?
C27 C28 C29 112.56(19) . . ?
C27 C28 H28A 109.1 . . ?
C29 C28 H28A 109.1 . . ?
C27 C28 H28B 109.1 . . ?
C29 C28 H28B 109.1 . . ?
H28A C28 H28B 107.8 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
H1W1 O1W H2W1 103(3) . . ?

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
C12 N1 N2 C16 179.51(15) . . . . ?
N4 C1 N3 C6 -148.38(19) . . . . ?
N5 C1 N3 C6 31.6(3) . . . . ?
N3 C1 N4 C2 -148.4(2) . . . . ?
N5 C1 N4 C2 31.6(3) . . . . ?
N3 C1 N4 C3 19.4(3) . . . . ?
N5 C1 N4 C3 -160.6(2) . . . . ?
N3 C1 N5 C5 -144.7(2) . . . . ?
N4 C1 N5 C5 35.3(3) . . . . ?
N3 C1 N5 C4 34.5(3) . . . . ?
N4 C1 N5 C4 -145.5(2) . . . . ?
C1 N3 C6 C7 141.74(19) . . . . ?
N3 C6 C7 C8 -64.5(2) . . . . ?
C6 C7 C8 C9 173.67(17) . . . . ?
C15 O1 C9 C8 -168.11(16) . . . . ?
C7 C8 C9 O1 179.73(17) . . . . ?
C15 C10 C11 C12 -0.2(3) . . . . ?
C10 C11 C12 C13 -0.9(3) . . . . ?
C10 C11 C12 N1 179.85(18) . . . . ?
N2 N1 C12 C13 -179.27(17) . . . . ?
N2 N1 C12 C11 0.0(3) . . . . ?
C11 C12 C13 C14 1.0(3) . . . . ?
N1 C12 C13 C14 -179.71(18) . . . . ?
C12 C13 C14 C15 0.0(3) . . . . ?
C9 O1 C15 C14 -6.9(3) . . . . ?
C9 O1 C15 C10 172.92(18) . . . . ?
C13 C14 C15 O1 178.77(18) . . . . ?
C13 C14 C15 C10 -1.1(3) . . . . ?
C11 C10 C15 O1 -178.70(17) . . . . ?
C11 C10 C15 C14 1.2(3) . . . . ?
N1 N2 C16 C17 -167.88(18) . . . . ?
N1 N2 C16 C21 12.6(3) . . . . ?
C21 C16 C17 C18 -2.7(3) . . . . ?
N2 C16 C17 C18 177.75(18) . . . . ?
C16 C17 C18 C19 1.0(3) . . . . ?
C22 O2 C19 C20 176.61(18) . . . . ?
C22 O2 C19 C18 -2.7(3) . . . . ?
C17 C18 C19 O2 -179.46(18) . . . . ?
C17 C18 C19 C20 1.2(3) . . . . ?
O2 C19 C20 C21 178.82(18) . . . . ?
C18 C19 C20 C21 -1.8(3) . . . . ?
C19 C20 C21 C16 0.1(3) . . . . ?
C17 C16 C21 C20 2.1(3) . . . . ?
N2 C16 C21 C20 -178.35(18) . . . . ?
C19 O2 C22 C23 -179.73(17) . . . . ?
O2 C22 C23 C24 177.24(17) . . . . ?
C22 C23 C24 C25 -178.39(17) . . . . ?
C23 C24 C25 C26 173.98(17) . . . . ?
C24 C25 C26 C27 178.10(17) . . . . ?
C25 C26 C27 C28 178.18(18) . . . . ?
C26 C27 C28 C29 -177.35(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        28.36
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.078
####################################################################### 
# 
# 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_s2086lm
_database_code_depnum_ccdc_archive 'CCDC 1030120'
_audit_update_record             
;
2014-10-20 deposited with the CCDC.
2014-12-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 '6a.Cl' 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H46 N5 O2, Cl, 2(C H Cl3)'
_chemical_formula_sum            'C31 H48 Cl7 N5 O2'
_chemical_formula_weight         770.89

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.7566(5)
_cell_length_b                   9.1438(5)
_cell_length_c                   42.575(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.250(3)
_cell_angle_gamma                90.00
_cell_volume                     3797.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5190
_cell_measurement_theta_min      1.91
_cell_measurement_theta_max      25.14

_exptl_crystal_description       plates
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1616
_exptl_absorpt_coefficient_mu    0.558
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6989
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'Blessing, 1995'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  Triumph
_diffrn_measurement_device_type  'Bruker Kappa APEXII Duo'
_diffrn_measurement_method       'Omega + Phi Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            27166
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_sigmaI/netI    0.0443
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         25.14
_reflns_number_total             6758
_reflns_number_gt                5190
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEXII Software Suite, 2008'
_computing_cell_refinement       'Bruker APEXII Software Suite, 2008'
_computing_data_reduction        'Bruker APEXII Software Suite, 2008'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL-plus, XP (Sheldrick, 1991)'
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0290P)²+2.3191P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6758
_refine_ls_number_parameters     415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.0827
_refine_ls_wR_factor_gt          0.0780
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.69174(6) 0.54314(6) 0.210236(14) 0.02278(14) Uani 1 1 d . . .
O1 O 0.04679(15) 0.34673(17) 0.62833(4) 0.0218(4) Uani 1 1 d . . .
N1 N 0.54002(19) 0.2490(2) 0.56924(4) 0.0193(4) Uani 1 1 d . . .
C1 C -0.4764(2) 0.3746(3) 0.70540(5) 0.0166(5) Uani 1 1 d . . .
O2 O 1.11295(15) 0.19441(17) 0.51111(4) 0.0218(4) Uani 1 1 d . . .
N2 N 0.63118(18) 0.3468(2) 0.57073(4) 0.0195(4) Uani 1 1 d . . .
C2 C -0.5733(2) 0.1858(3) 0.67091(6) 0.0234(5) Uani 1 1 d . . .
H2A H -0.4902 0.1999 0.6587 0.035 Uiso 1 1 calc R . .
H2B H -0.6534 0.1831 0.6566 0.035 Uiso 1 1 calc R . .
H2C H -0.5667 0.0933 0.6825 0.035 Uiso 1 1 calc R . .
N3 N -0.35524(18) 0.3075(2) 0.70538(4) 0.0178(4) Uani 1 1 d . . .
H3 H -0.352(2) 0.212(3) 0.7052(6) 0.023(7) Uiso 1 1 d . . .
C3 C -0.7250(2) 0.3289(3) 0.70532(6) 0.0233(5) Uani 1 1 d . . .
H3A H -0.7183 0.3830 0.7252 0.035 Uiso 1 1 calc R . .
H3B H -0.7684 0.2339 0.7089 0.035 Uiso 1 1 calc R . .
H3C H -0.7804 0.3849 0.6901 0.035 Uiso 1 1 calc R . .
N4 N -0.58748(18) 0.3065(2) 0.69305(4) 0.0185(4) Uani 1 1 d . . .
C4 C -0.5882(2) 0.6162(3) 0.70579(6) 0.0274(6) Uani 1 1 d . . .
H4A H -0.6238 0.5861 0.6851 0.041 Uiso 1 1 calc R . .
H4B H -0.5446 0.7123 0.7041 0.041 Uiso 1 1 calc R . .
H4C H -0.6638 0.6217 0.7205 0.041 Uiso 1 1 calc R . .
N5 N -0.48753(17) 0.5095(2) 0.71715(4) 0.0183(4) Uani 1 1 d . . .
C5 C -0.4030(2) 0.5598(3) 0.74390(6) 0.0249(6) Uani 1 1 d . . .
H5A H -0.3526 0.4768 0.7530 0.037 Uiso 1 1 calc R . .
H5B H -0.4620 0.6026 0.7598 0.037 Uiso 1 1 calc R . .
H5C H -0.3379 0.6336 0.7368 0.037 Uiso 1 1 calc R . .
C6 C -0.2230(2) 0.3828(3) 0.70405(5) 0.0194(5) Uani 1 1 d . . .
H6A H -0.1833 0.3924 0.7256 0.023 Uiso 1 1 calc R . .
H6B H -0.2369 0.4824 0.6954 0.023 Uiso 1 1 calc R . .
C7 C -0.1237(2) 0.2995(3) 0.68360(5) 0.0200(5) Uani 1 1 d . . .
H7A H -0.0334 0.3487 0.6848 0.024 Uiso 1 1 calc R . .
H7B H -0.1117 0.1997 0.6923 0.024 Uiso 1 1 calc R . .
C8 C -0.1687(2) 0.2874(3) 0.64941(6) 0.0228(5) Uani 1 1 d . . .
H8A H -0.2478 0.2199 0.6476 0.027 Uiso 1 1 calc R . .
H8B H -0.1991 0.3847 0.6418 0.027 Uiso 1 1 calc R . .
C9 C -0.0554(2) 0.2325(3) 0.62895(6) 0.0214(5) Uani 1 1 d . . .
H9A H -0.0154 0.1414 0.6378 0.026 Uiso 1 1 calc R . .
H9B H -0.0911 0.2121 0.6074 0.026 Uiso 1 1 calc R . .
C10 C 0.1652(2) 0.3182(3) 0.61321(5) 0.0191(5) Uani 1 1 d . . .
C11 C 0.2635(2) 0.4296(3) 0.61450(5) 0.0196(5) Uani 1 1 d . . .
H11 H 0.2439 0.5180 0.6252 0.023 Uiso 1 1 calc R . .
C12 C 0.3881(2) 0.4127(3) 0.60042(5) 0.0190(5) Uani 1 1 d . . .
H12 H 0.4542 0.4890 0.6014 0.023 Uiso 1 1 calc R . .
C13 C 0.4166(2) 0.2823(3) 0.58473(5) 0.0173(5) Uani 1 1 d . . .
C14 C 0.3184(2) 0.1730(3) 0.58342(5) 0.0200(5) Uani 1 1 d . . .
H14 H 0.3378 0.0847 0.5727 0.024 Uiso 1 1 calc R . .
C15 C 0.1929(2) 0.1895(3) 0.59738(5) 0.0193(5) Uani 1 1 d . . .
H15 H 0.1264 0.1136 0.5962 0.023 Uiso 1 1 calc R . .
C16 C 0.7527(2) 0.3048(3) 0.55498(5) 0.0174(5) Uani 1 1 d . . .
C17 C 0.8575(2) 0.4071(3) 0.55385(5) 0.0205(5) Uani 1 1 d . . .
H17 H 0.8455 0.5004 0.5632 0.025 Uiso 1 1 calc R . .
C18 C 0.9799(2) 0.3750(3) 0.53915(6) 0.0217(5) Uani 1 1 d . . .
H18 H 1.0506 0.4462 0.5382 0.026 Uiso 1 1 calc R . .
C19 C 0.9976(2) 0.2387(3) 0.52594(5) 0.0184(5) Uani 1 1 d . . .
C20 C 0.8929(2) 0.1343(3) 0.52724(5) 0.0194(5) Uani 1 1 d . . .
H20 H 0.9055 0.0402 0.5183 0.023 Uiso 1 1 calc R . .
C21 C 0.7724(2) 0.1678(3) 0.54144(5) 0.0204(5) Uani 1 1 d . . .
H21 H 0.7013 0.0969 0.5421 0.024 Uiso 1 1 calc R . .
C22 C 1.2231(2) 0.2969(3) 0.50708(6) 0.0199(5) Uani 1 1 d . . .
H22A H 1.2598 0.3301 0.5277 0.024 Uiso 1 1 calc R . .
H22B H 1.1907 0.3833 0.4950 0.024 Uiso 1 1 calc R . .
C23 C 1.3314(2) 0.2162(3) 0.48934(6) 0.0231(5) Uani 1 1 d . . .
H23A H 1.2918 0.1847 0.4688 0.028 Uiso 1 1 calc R . .
H23B H 1.3571 0.1270 0.5013 0.028 Uiso 1 1 calc R . .
C24 C 1.4611(2) 0.3050(3) 0.48351(6) 0.0211(5) Uani 1 1 d . . .
H24A H 1.4374 0.3916 0.4706 0.025 Uiso 1 1 calc R . .
H24B H 1.5000 0.3399 0.5038 0.025 Uiso 1 1 calc R . .
C25 C 1.5681(2) 0.2136(3) 0.46678(6) 0.0233(5) Uani 1 1 d . . .
H25A H 1.5886 0.1259 0.4797 0.028 Uiso 1 1 calc R . .
H25B H 1.5280 0.1797 0.4465 0.028 Uiso 1 1 calc R . .
C26 C 1.7021(2) 0.2920(3) 0.46039(6) 0.0205(5) Uani 1 1 d . . .
H26A H 1.7445 0.3239 0.4806 0.025 Uiso 1 1 calc R . .
H26B H 1.6827 0.3805 0.4476 0.025 Uiso 1 1 calc R . .
C27 C 1.8026(2) 0.1953(3) 0.44315(5) 0.0202(5) Uani 1 1 d . . .
H27A H 1.8232 0.1084 0.4563 0.024 Uiso 1 1 calc R . .
H27B H 1.7578 0.1604 0.4235 0.024 Uiso 1 1 calc R . .
C28 C 1.9367(2) 0.2690(3) 0.43510(6) 0.0224(5) Uani 1 1 d . . .
H28A H 1.9864 0.2951 0.4548 0.027 Uiso 1 1 calc R . .
H28B H 1.9163 0.3609 0.4236 0.027 Uiso 1 1 calc R . .
C29 C 2.0292(2) 0.1744(3) 0.41524(6) 0.0296(6) Uani 1 1 d . . .
H29A H 2.0518 0.0842 0.4267 0.044 Uiso 1 1 calc R . .
H29B H 2.1137 0.2279 0.4109 0.044 Uiso 1 1 calc R . .
H29C H 1.9817 0.1501 0.3954 0.044 Uiso 1 1 calc R . .
C1X C 1.0028(2) 0.2192(3) 0.29978(6) 0.0263(6) Uani 1 1 d . . .
H1X H 1.0973 0.1768 0.3003 0.032 Uiso 1 1 calc R . .
Cl1X Cl 0.98421(7) 0.33349(8) 0.332768(15) 0.03408(16) Uani 1 1 d . . .
Cl2X Cl 0.97998(7) 0.32152(8) 0.265143(15) 0.03783(17) Uani 1 1 d . . .
Cl3X Cl 0.88217(7) 0.07507(8) 0.300958(18) 0.04049(18) Uani 1 1 d . . .
C2X C 0.5774(2) 0.6580(3) 0.13874(6) 0.0257(6) Uani 1 1 d . . .
H2X H 0.6032 0.6197 0.1601 0.031 Uiso 1 1 calc R . .
Cl4X Cl 0.39635(6) 0.67149(8) 0.135669(16) 0.03224(16) Uani 1 1 d . . .
Cl5X Cl 0.63660(7) 0.53532(7) 0.110329(15) 0.03238(16) Uani 1 1 d . . .
Cl6X Cl 0.65170(7) 0.83152(8) 0.13417(2) 0.04321(19) 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 C10 1.360(3) . ?
O1 C9 1.444(3) . ?
N1 N2 1.262(3) . ?
N1 C13 1.418(3) . ?
C1 N3 1.332(3) . ?
C1 N5 1.336(3) . ?
C1 N4 1.347(3) . ?
O2 C19 1.364(3) . ?
O2 C22 1.439(3) . ?
N2 C16 1.427(3) . ?
C2 N4 1.460(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
N3 C6 1.465(3) . ?
N3 H3 0.87(3) . ?
C3 N4 1.465(3) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 N5 1.459(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
N5 C5 1.465(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.521(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.515(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.509(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C15 1.386(3) . ?
C10 C11 1.399(3) . ?
C11 C12 1.376(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.398(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(3) . ?
C14 C15 1.381(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.388(3) . ?
C16 C21 1.394(3) . ?
C17 C18 1.392(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.380(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.399(3) . ?
C20 C21 1.369(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.506(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.528(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.526(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.521(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.521(3) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.518(3) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.520(3) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C1X Cl2X 1.756(3) . ?
C1X Cl1X 1.763(3) . ?
C1X Cl3X 1.768(2) . ?
C1X H1X 1.0000 . ?
C2X Cl6X 1.756(3) . ?
C2X Cl5X 1.756(3) . ?
C2X Cl4X 1.773(2) . ?
C2X H2X 1.0000 . ?

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
C10 O1 C9 117.61(18) . . ?
N2 N1 C13 115.41(19) . . ?
N3 C1 N5 120.3(2) . . ?
N3 C1 N4 119.6(2) . . ?
N5 C1 N4 120.1(2) . . ?
C19 O2 C22 119.20(18) . . ?
N1 N2 C16 112.15(19) . . ?
N4 C2 H2A 109.5 . . ?
N4 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N4 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 N3 C6 124.5(2) . . ?
C1 N3 H3 119.4(16) . . ?
C6 N3 H3 116.1(16) . . ?
N4 C3 H3A 109.5 . . ?
N4 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N4 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 N4 C2 120.98(19) . . ?
C1 N4 C3 122.11(19) . . ?
C2 N4 C3 115.89(18) . . ?
N5 C4 H4A 109.5 . . ?
N5 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N5 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C1 N5 C4 123.54(19) . . ?
C1 N5 C5 122.14(19) . . ?
C4 N5 C5 114.25(19) . . ?
N5 C5 H5A 109.5 . . ?
N5 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N5 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N3 C6 C7 111.02(19) . . ?
N3 C6 H6A 109.4 . . ?
C7 C6 H6A 109.4 . . ?
N3 C6 H6B 109.4 . . ?
C7 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C8 C7 C6 114.31(19) . . ?
C8 C7 H7A 108.7 . . ?
C6 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C9 C8 C7 112.24(19) . . ?
C9 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
O1 C9 C8 106.52(19) . . ?
O1 C9 H9A 110.4 . . ?
C8 C9 H9A 110.4 . . ?
O1 C9 H9B 110.4 . . ?
C8 C9 H9B 110.4 . . ?
H9A C9 H9B 108.6 . . ?
O1 C10 C15 124.7(2) . . ?
O1 C10 C11 115.5(2) . . ?
C15 C10 C11 119.8(2) . . ?
C12 C11 C10 120.9(2) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 119.4(2) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C14 C13 C12 119.3(2) . . ?
C14 C13 N1 114.9(2) . . ?
C12 C13 N1 125.8(2) . . ?
C15 C14 C13 121.6(2) . . ?
C15 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C14 C15 C10 119.1(2) . . ?
C14 C15 H15 120.5 . . ?
C10 C15 H15 120.5 . . ?
C17 C16 C21 118.9(2) . . ?
C17 C16 N2 117.1(2) . . ?
C21 C16 N2 124.0(2) . . ?
C16 C17 C18 120.9(2) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C19 C18 C17 119.3(2) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
O2 C19 C18 124.6(2) . . ?
O2 C19 C20 115.2(2) . . ?
C18 C19 C20 120.2(2) . . ?
C21 C20 C19 119.9(2) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C16 120.8(2) . . ?
C20 C21 H21 119.6 . . ?
C16 C21 H21 119.6 . . ?
O2 C22 C23 105.96(18) . . ?
O2 C22 H22A 110.5 . . ?
C23 C22 H22A 110.5 . . ?
O2 C22 H22B 110.5 . . ?
C23 C22 H22B 110.5 . . ?
H22A C22 H22B 108.7 . . ?
C22 C23 C24 114.5(2) . . ?
C22 C23 H23A 108.6 . . ?
C24 C23 H23A 108.6 . . ?
C22 C23 H23B 108.6 . . ?
C24 C23 H23B 108.6 . . ?
H23A C23 H23B 107.6 . . ?
C25 C24 C23 111.2(2) . . ?
C25 C24 H24A 109.4 . . ?
C23 C24 H24A 109.4 . . ?
C25 C24 H24B 109.4 . . ?
C23 C24 H24B 109.4 . . ?
H24A C24 H24B 108.0 . . ?
C26 C25 C24 115.1(2) . . ?
C26 C25 H25A 108.5 . . ?
C24 C25 H25A 108.5 . . ?
C26 C25 H25B 108.5 . . ?
C24 C25 H25B 108.5 . . ?
H25A C25 H25B 107.5 . . ?
C25 C26 C27 112.2(2) . . ?
C25 C26 H26A 109.2 . . ?
C27 C26 H26A 109.2 . . ?
C25 C26 H26B 109.2 . . ?
C27 C26 H26B 109.2 . . ?
H26A C26 H26B 107.9 . . ?
C28 C27 C26 114.7(2) . . ?
C28 C27 H27A 108.6 . . ?
C26 C27 H27A 108.6 . . ?
C28 C27 H27B 108.6 . . ?
C26 C27 H27B 108.6 . . ?
H27A C27 H27B 107.6 . . ?
C27 C28 C29 113.4(2) . . ?
C27 C28 H28A 108.9 . . ?
C29 C28 H28A 108.9 . . ?
C27 C28 H28B 108.9 . . ?
C29 C28 H28B 108.9 . . ?
H28A C28 H28B 107.7 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
Cl2X C1X Cl1X 109.88(14) . . ?
Cl2X C1X Cl3X 110.40(13) . . ?
Cl1X C1X Cl3X 109.84(14) . . ?
Cl2X C1X H1X 108.9 . . ?
Cl1X C1X H1X 108.9 . . ?
Cl3X C1X H1X 108.9 . . ?
Cl6X C2X Cl5X 110.99(14) . . ?
Cl6X C2X Cl4X 110.00(13) . . ?
Cl5X C2X Cl4X 109.60(13) . . ?
Cl6X C2X H2X 108.7 . . ?
Cl5X C2X H2X 108.7 . . ?
Cl4X C2X H2X 108.7 . . ?

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
C13 N1 N2 C16 179.27(18) . . . . ?
N5 C1 N3 C6 -28.4(3) . . . . ?
N4 C1 N3 C6 150.6(2) . . . . ?
N3 C1 N4 C2 -20.3(3) . . . . ?
N5 C1 N4 C2 158.7(2) . . . . ?
N3 C1 N4 C3 147.6(2) . . . . ?
N5 C1 N4 C3 -33.3(3) . . . . ?
N3 C1 N5 C4 149.5(2) . . . . ?
N4 C1 N5 C4 -29.5(3) . . . . ?
N3 C1 N5 C5 -33.8(3) . . . . ?
N4 C1 N5 C5 147.2(2) . . . . ?
C1 N3 C6 C7 -141.7(2) . . . . ?
N3 C6 C7 C8 63.3(3) . . . . ?
C6 C7 C8 C9 168.1(2) . . . . ?
C10 O1 C9 C8 174.99(19) . . . . ?
C7 C8 C9 O1 -68.3(2) . . . . ?
C9 O1 C10 C15 2.5(3) . . . . ?
C9 O1 C10 C11 -177.15(19) . . . . ?
O1 C10 C11 C12 179.2(2) . . . . ?
C15 C10 C11 C12 -0.5(3) . . . . ?
C10 C11 C12 C13 -0.2(3) . . . . ?
C11 C12 C13 C14 0.6(3) . . . . ?
C11 C12 C13 N1 -179.9(2) . . . . ?
N2 N1 C13 C14 -178.9(2) . . . . ?
N2 N1 C13 C12 1.6(3) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
N1 C13 C14 C15 -179.9(2) . . . . ?
C13 C14 C15 C10 -0.3(3) . . . . ?
O1 C10 C15 C14 -178.9(2) . . . . ?
C11 C10 C15 C14 0.7(3) . . . . ?
N1 N2 C16 C17 177.0(2) . . . . ?
N1 N2 C16 C21 -4.3(3) . . . . ?
C21 C16 C17 C18 0.8(3) . . . . ?
N2 C16 C17 C18 179.5(2) . . . . ?
C16 C17 C18 C19 -0.9(3) . . . . ?
C22 O2 C19 C18 -3.5(3) . . . . ?
C22 O2 C19 C20 176.57(19) . . . . ?
C17 C18 C19 O2 -179.6(2) . . . . ?
C17 C18 C19 C20 0.3(3) . . . . ?
O2 C19 C20 C21 -179.6(2) . . . . ?
C18 C19 C20 C21 0.5(3) . . . . ?
C19 C20 C21 C16 -0.6(3) . . . . ?
C17 C16 C21 C20 0.0(3) . . . . ?
N2 C16 C21 C20 -178.7(2) . . . . ?
C19 O2 C22 C23 -178.45(19) . . . . ?
O2 C22 C23 C24 -178.00(19) . . . . ?
C22 C23 C24 C25 177.4(2) . . . . ?
C23 C24 C25 C26 -179.1(2) . . . . ?
C24 C25 C26 C27 -179.0(2) . . . . ?
C25 C26 C27 C28 178.0(2) . . . . ?
C26 C27 C28 C29 -174.6(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.14
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.053
