# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1478704'
_audit_update_record             
;
2016-05-09 deposited with the CCDC.
2016-08-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C72 H57 N7'
_chemical_formula_weight         1020.25

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'I 2/a'

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

_cell_length_a                   27.518(12)
_cell_length_b                   9.894(4)
_cell_length_c                   45.122(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.22(2)
_cell_angle_gamma                90.00
_cell_volume                     11796(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2436
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      26.32

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             4304
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.814
_exptl_absorpt_correction_T_max  0.856
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX II CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            31604
_diffrn_reflns_av_R_equivalents  0.0879
_diffrn_reflns_av_sigmaI/netI    0.1066
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_limit_l_max       55
_diffrn_reflns_theta_min         1.88
_diffrn_reflns_theta_max         26.00
_reflns_number_total             11548
_reflns_number_gt                4563
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_reduction        SAINT-Plus
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XP (Sheldrick, 1998)'
_computing_publication_material  XP

_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)+(0.0462P)²+0.0000P] 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     SHELXL
_refine_ls_extinction_coef       0.00042(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         11548
_refine_ls_number_parameters     721
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.1743
_refine_ls_R_factor_gt           0.0619
_refine_ls_wR_factor_ref         0.1575
_refine_ls_wR_factor_gt          0.1232
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.026
_refine_ls_shift/su_mean         0.001

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
N3 N 0.13993(9) 0.4674(3) 0.04466(6) 0.0518(7) Uani 1 1 d . . .
N4 N 0.13206(8) 0.2448(2) 0.04852(5) 0.0523(6) Uani 1 1 d . . .
C34 C 0.03981(11) 0.4794(3) 0.15942(7) 0.0561(8) Uani 1 1 d . . .
C48 C 0.12064(13) 0.4808(4) 0.20105(7) 0.0684(9) Uani 1 1 d . . .
C53 C 0.13789(15) 0.3513(5) 0.20050(8) 0.0886(11) Uani 1 1 d . . .
H53A H 0.1152 0.2832 0.1916 0.106 Uiso 1 1 calc R . .
C52 C 0.1887(2) 0.3196(6) 0.21298(10) 0.1163(15) Uani 1 1 d . . .
H52A H 0.1998 0.2312 0.2123 0.140 Uiso 1 1 calc R . .
C51 C 0.2217(2) 0.4176(7) 0.22601(11) 0.1253(18) Uani 1 1 d . . .
H51A H 0.2557 0.3965 0.2344 0.150 Uiso 1 1 calc R . .
C50 C 0.20561(19) 0.5480(6) 0.22701(10) 0.1208(16) Uani 1 1 d . . .
H50A H 0.2287 0.6155 0.2358 0.145 Uiso 1 1 calc R . .
C49 C 0.15469(15) 0.5790(4) 0.21488(8) 0.0937(12) Uani 1 1 d . . .
H49A H 0.1436 0.6670 0.2162 0.112 Uiso 1 1 calc R . .
C35 C 0.06586(12) 0.5137(3) 0.18857(7) 0.0610(8) Uani 1 1 d . . .
C42 C 0.04290(12) 0.5846(4) 0.21033(7) 0.0630(9) Uani 1 1 d . . .
C47 C 0.05702(13) 0.5524(4) 0.24128(8) 0.0852(11) Uani 1 1 d . . .
H47A H 0.0807 0.4843 0.2485 0.102 Uiso 1 1 calc R . .
C46 C 0.03650(19) 0.6199(5) 0.26166(9) 0.1111(15) Uani 1 1 d . . .
H46A H 0.0460 0.5961 0.2824 0.133 Uiso 1 1 calc R . .
C45 C 0.00233(19) 0.7213(5) 0.25160(11) 0.1132(15) Uani 1 1 d . . .
H45A H -0.0118 0.7656 0.2654 0.136 Uiso 1 1 calc R . .
C44 C -0.01090(14) 0.7571(4) 0.22145(10) 0.0965(12) Uani 1 1 d . . .
H44A H -0.0338 0.8271 0.2145 0.116 Uiso 1 1 calc R . .
C43 C 0.00945(13) 0.6903(4) 0.20109(8) 0.0779(10) Uani 1 1 d . . .
H43A H 0.0005 0.7171 0.1805 0.093 Uiso 1 1 calc R . .
C36 C -0.01567(12) 0.4874(3) 0.14750(8) 0.0619(9) Uani 1 1 d . . .
C41 C -0.04751(14) 0.4309(4) 0.16275(9) 0.0898(12) Uani 1 1 d . . .
H41A H -0.0340 0.3855 0.1813 0.108 Uiso 1 1 calc R . .
C40 C -0.10027(18) 0.4413(5) 0.15054(12) 0.1116(15) Uani 1 1 d U . .
H40A H -0.1219 0.4036 0.1608 0.134 Uiso 1 1 calc R . .
C39 C -0.11875(19) 0.5068(5) 0.12376(14) 0.1210(17) Uani 1 1 d U . .
H39A H -0.1537 0.5138 0.1158 0.145 Uiso 1 1 calc R . .
C38 C -0.08888(18) 0.5634(5) 0.10774(11) 0.1142(15) Uani 1 1 d . . .
H38A H -0.1028 0.6084 0.0892 0.137 Uiso 1 1 calc R . .
C37 C -0.03735(14) 0.5518(4) 0.11983(8) 0.0809(10) Uani 1 1 d . . .
H37A H -0.0164 0.5888 0.1090 0.097 Uiso 1 1 calc R . .
C54 C 0.06626(10) 0.4394(3) 0.13619(6) 0.0514(8) Uani 1 1 d . . .
C59 C 0.05607(11) 0.3200(3) 0.11963(7) 0.0591(8) Uani 1 1 d . . .
H59A H 0.0347 0.2568 0.1247 0.071 Uiso 1 1 calc R . .
C58 C 0.07668(10) 0.2927(3) 0.09588(7) 0.0584(8) Uani 1 1 d . . .
H58A H 0.0697 0.2107 0.0855 0.070 Uiso 1 1 calc R . .
C57 C 0.10769(10) 0.3855(3) 0.08717(6) 0.0470(7) Uani 1 1 d . . .
C56 C 0.11912(11) 0.5030(3) 0.10417(6) 0.0575(8) Uani 1 1 d . . .
H56A H 0.1410 0.5655 0.0993 0.069 Uiso 1 1 calc R . .
C55 C 0.09871(11) 0.5292(3) 0.12817(7) 0.0618(8) Uani 1 1 d . . .
H55A H 0.1070 0.6093 0.1392 0.074 Uiso 1 1 calc R . .
C60 C 0.12651(9) 0.3641(3) 0.06045(7) 0.0469(7) Uani 1 1 d . . .
C66 C 0.15582(10) 0.4124(3) 0.02094(7) 0.0494(7) Uani 1 1 d . . .
C65 C 0.17339(11) 0.4705(3) -0.00197(7) 0.0678(9) Uani 1 1 d . . .
H65A H 0.1765 0.5636 -0.0035 0.081 Uiso 1 1 calc R . .
C64 C 0.18600(12) 0.3836(4) -0.02223(8) 0.0783(10) Uani 1 1 d . . .
H64A H 0.1976 0.4186 -0.0381 0.094 Uiso 1 1 calc R . .
C63 C 0.18187(13) 0.2446(4) -0.01967(8) 0.0838(11) Uani 1 1 d . . .
H63A H 0.1911 0.1885 -0.0337 0.101 Uiso 1 1 calc R . .
C62 C 0.16445(12) 0.1885(3) 0.00310(8) 0.0730(10) Uani 1 1 d . . .
H62A H 0.1617 0.0953 0.0047 0.088 Uiso 1 1 calc R . .
C61 C 0.15101(10) 0.2740(3) 0.02364(7) 0.0521(8) Uani 1 1 d . . .
N1 N 0.11047(9) 0.9686(3) 0.05568(5) 0.0509(6) Uani 1 1 d . . .
N2 N 0.12018(8) 0.7439(2) 0.05664(5) 0.0514(6) Uani 1 1 d . . .
C2 C 0.38850(11) 0.9744(3) 0.12309(7) 0.0546(8) Uani 1 1 d . . .
C1 C 0.36047(10) 0.9130(3) 0.09741(7) 0.0504(7) Uani 1 1 d . . .
C22 C 0.44350(11) 1.0006(3) 0.12915(7) 0.0575(8) Uani 1 1 d . . .
C23 C 0.47717(12) 0.9537(4) 0.15615(7) 0.0737(10) Uani 1 1 d . . .
H23A H 0.4651 0.9037 0.1701 0.088 Uiso 1 1 calc R . .
C24 C 0.52799(15) 0.9800(5) 0.16257(9) 0.0978(13) Uani 1 1 d . . .
H24A H 0.5501 0.9472 0.1807 0.117 Uiso 1 1 calc R . .
C25 C 0.54618(15) 1.0541(5) 0.14249(12) 0.1051(15) Uani 1 1 d . . .
H25A H 0.5807 1.0719 0.1469 0.126 Uiso 1 1 calc R . .
C26 C 0.51381(16) 1.1023(4) 0.11589(10) 0.0956(13) Uani 1 1 d . . .
H26A H 0.5262 1.1533 0.1023 0.115 Uiso 1 1 calc R . .
C27 C 0.46286(13) 1.0752(4) 0.10920(8) 0.0787(10) Uani 1 1 d . . .
H27A H 0.4411 1.1077 0.0909 0.094 Uiso 1 1 calc R . .
C28 C 0.38233(10) 0.8507(3) 0.07407(6) 0.0500(7) Uani 1 1 d . . .
C29 C 0.42247(11) 0.7640(3) 0.08194(7) 0.0628(9) Uani 1 1 d . . .
H29A H 0.4375 0.7443 0.1026 0.075 Uiso 1 1 calc R . .
C30 C 0.44110(12) 0.7051(4) 0.05957(8) 0.0758(10) Uani 1 1 d . . .
H30A H 0.4684 0.6460 0.0654 0.091 Uiso 1 1 calc R . .
C31 C 0.41996(14) 0.7326(4) 0.02926(8) 0.0748(10) Uani 1 1 d . . .
H31A H 0.4328 0.6935 0.0143 0.090 Uiso 1 1 calc R . .
C32 C 0.37954(15) 0.8187(4) 0.02098(7) 0.0809(11) Uani 1 1 d . . .
H32A H 0.3648 0.8383 0.0003 0.097 Uiso 1 1 calc R . .
C33 C 0.36058(12) 0.8763(3) 0.04314(7) 0.0699(9) Uani 1 1 d . . .
H33A H 0.3327 0.9334 0.0372 0.084 Uiso 1 1 calc R . .
C3 C 0.30430(10) 0.9019(3) 0.08994(6) 0.0512(7) Uani 1 1 d . . .
C4 C 0.28100(11) 0.7777(3) 0.08235(7) 0.0643(9) Uani 1 1 d . . .
H4A H 0.3008 0.7008 0.0833 0.077 Uiso 1 1 calc R . .
C5 C 0.22931(11) 0.7658(3) 0.07343(7) 0.0609(8) Uani 1 1 d . . .
H5A H 0.2147 0.6807 0.0690 0.073 Uiso 1 1 calc R . .
C6 C 0.19844(10) 0.8779(3) 0.07097(6) 0.0449(7) Uani 1 1 d . . .
C7 C 0.22165(11) 1.0020(3) 0.07835(6) 0.0565(8) Uani 1 1 d . . .
H7A H 0.2018 1.0791 0.0769 0.068 Uiso 1 1 calc R . .
C8 C 0.27362(11) 1.0140(3) 0.08779(6) 0.0599(8) Uani 1 1 d . . .
H8A H 0.2882 1.0988 0.0928 0.072 Uiso 1 1 calc R . .
C9 C 0.14342(11) 0.8625(3) 0.06121(6) 0.0475(7) Uani 1 1 d . . .
C15 C 0.06906(11) 0.7741(3) 0.04800(6) 0.0496(7) Uani 1 1 d . . .
C14 C 0.02742(11) 0.6888(3) 0.04083(7) 0.0667(9) Uani 1 1 d . . .
H14A H 0.0314 0.5954 0.0416 0.080 Uiso 1 1 calc R . .
C13 C -0.01971(12) 0.7465(4) 0.03252(7) 0.0766(10) Uani 1 1 d . . .
H13A H -0.0482 0.6914 0.0275 0.092 Uiso 1 1 calc R . .
C12 C -0.02546(12) 0.8856(4) 0.03148(7) 0.0790(10) Uani 1 1 d . . .
H12A H -0.0580 0.9213 0.0257 0.095 Uiso 1 1 calc R . .
C11 C 0.01471(12) 0.9726(3) 0.03853(7) 0.0658(9) Uani 1 1 d . . .
H11A H 0.0103 1.0659 0.0377 0.079 Uiso 1 1 calc R . .
C10 C 0.06266(11) 0.9138(3) 0.04708(6) 0.0492(7) Uani 1 1 d . . .
C16 C 0.36704(10) 1.0234(4) 0.14825(7) 0.0572(8) Uani 1 1 d . . .
C17 C 0.34387(11) 0.9365(4) 0.16410(8) 0.0776(10) Uani 1 1 d . . .
H17A H 0.3397 0.8459 0.1584 0.093 Uiso 1 1 calc R . .
C18 C 0.32694(14) 0.9834(5) 0.18824(9) 0.0955(13) Uani 1 1 d . . .
H18A H 0.3114 0.9241 0.1987 0.115 Uiso 1 1 calc R . .
C19 C 0.33278(15) 1.1158(6) 0.19685(9) 0.1012(15) Uani 1 1 d . . .
H19A H 0.3214 1.1466 0.2132 0.121 Uiso 1 1 calc R . .
C20 C 0.35533(14) 1.2026(5) 0.18139(9) 0.0982(13) Uani 1 1 d . . .
H20A H 0.3589 1.2934 0.1869 0.118 Uiso 1 1 calc R . .
C21 C 0.37283(12) 1.1554(4) 0.15758(8) 0.0792(10) Uani 1 1 d . . .
H21A H 0.3891 1.2150 0.1475 0.095 Uiso 1 1 calc R . .
N5 N 0.2518(2) 0.3986(7) 0.09877(17) 0.190(3) Uani 1 1 d . . .
C70 C 0.2402(2) 0.3537(9) 0.1197(2) 0.173(3) Uani 1 1 d . . .
C69 C 0.2236(3) 0.2842(9) 0.14205(15) 0.229(4) Uani 1 1 d U . .
H69A H 0.2360 0.3285 0.1616 0.344 Uiso 1 1 calc R . .
H69B H 0.2360 0.1930 0.1436 0.344 Uiso 1 1 calc R . .
H69C H 0.1872 0.2832 0.1362 0.344 Uiso 1 1 calc R . .
N6 N 0.1832(3) 0.9511(9) 0.1922(2) 0.290(5) Uani 1 1 d . . .
C73 C 0.2135(3) 0.7809(8) 0.15407(14) 0.222(3) Uani 1 1 d U . .
H73A H 0.1870 0.7647 0.1354 0.333 Uiso 1 1 calc R . .
H73B H 0.2237 0.6968 0.1646 0.333 Uiso 1 1 calc R . .
H73C H 0.2419 0.8214 0.1491 0.333 Uiso 1 1 calc R . .
C68 C 0.3543(4) 0.5783(10) 0.2259(3) 0.202(5) Uani 1 1 d . . .
N7 N 0.3212(4) 0.6223(12) 0.2059(3) 0.308(6) Uani 1 1 d . . .
C67 C 0.3896(3) 0.5275(9) 0.25155(18) 0.264(5) Uani 1 1 d . . .
H67A H 0.4113 0.5993 0.2618 0.396 Uiso 1 1 calc R . .
H67B H 0.4095 0.4594 0.2453 0.396 Uiso 1 1 calc R . .
H67C H 0.3726 0.4886 0.2654 0.396 Uiso 1 1 calc R . .
C72 C 0.1945(3) 0.8744(10) 0.1746(3) 0.206(4) Uani 1 1 d U . .
H1 H 0.1173(10) 1.062(3) 0.0546(6) 0.077(10) Uiso 1 1 d . . .
H2 H 0.1354(10) 0.555(3) 0.0492(6) 0.071(10) 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
N3 C60 1.355(3) . ?
N3 C66 1.376(3) . ?
N3 H2 0.90(3) . ?
N4 C60 1.324(3) . ?
N4 C61 1.394(3) . ?
C34 C35 1.354(4) . ?
C34 C36 1.472(4) . ?
C34 C54 1.487(4) . ?
C48 C53 1.369(5) . ?
C48 C49 1.373(4) . ?
C48 C35 1.490(4) . ?
C53 C52 1.388(5) . ?
C53 H53A 0.9300 . ?
C52 C51 1.346(6) . ?
C52 H52A 0.9300 . ?
C51 C50 1.368(6) . ?
C51 H51A 0.9300 . ?
C50 C49 1.389(5) . ?
C50 H50A 0.9300 . ?
C49 H49A 0.9300 . ?
C35 C42 1.484(4) . ?
C42 C47 1.378(4) . ?
C42 C43 1.379(4) . ?
C47 C46 1.379(5) . ?
C47 H47A 0.9300 . ?
C46 C45 1.363(5) . ?
C46 H46A 0.9300 . ?
C45 C44 1.354(5) . ?
C45 H45A 0.9300 . ?
C44 C43 1.372(4) . ?
C44 H44A 0.9300 . ?
C43 H43A 0.9300 . ?
C36 C41 1.375(4) . ?
C36 C37 1.380(4) . ?
C41 C40 1.405(5) . ?
C41 H41A 0.9300 . ?
C40 C39 1.340(6) . ?
C40 H40A 0.9300 . ?
C39 C38 1.358(6) . ?
C39 H39A 0.9300 . ?
C38 C37 1.375(5) . ?
C38 H38A 0.9300 . ?
C37 H37A 0.9300 . ?
C54 C55 1.378(4) . ?
C54 C59 1.384(4) . ?
C59 C58 1.372(3) . ?
C59 H59A 0.9300 . ?
C58 C57 1.383(3) . ?
C58 H58A 0.9300 . ?
C57 C56 1.379(4) . ?
C57 C60 1.455(4) . ?
C56 C55 1.377(4) . ?
C56 H56A 0.9300 . ?
C55 H55A 0.9300 . ?
C66 C65 1.383(4) . ?
C66 C61 1.384(4) . ?
C65 C64 1.368(4) . ?
C65 H65A 0.9300 . ?
C64 C63 1.388(4) . ?
C64 H64A 0.9300 . ?
C63 C62 1.367(4) . ?
C63 H63A 0.9300 . ?
C62 C61 1.379(4) . ?
C62 H62A 0.9300 . ?
N1 C9 1.364(3) . ?
N1 C10 1.375(3) . ?
N1 H1 0.95(3) . ?
N2 C9 1.325(3) . ?
N2 C15 1.384(3) . ?
C2 C1 1.345(4) . ?
C2 C22 1.484(4) . ?
C2 C16 1.499(4) . ?
C1 C28 1.485(4) . ?
C1 C3 1.491(4) . ?
C22 C27 1.381(4) . ?
C22 C23 1.388(4) . ?
C23 C24 1.372(5) . ?
C23 H23A 0.9300 . ?
C24 C25 1.365(5) . ?
C24 H24A 0.9300 . ?
C25 C26 1.365(5) . ?
C25 H25A 0.9300 . ?
C26 C27 1.376(4) . ?
C26 H26A 0.9300 . ?
C27 H27A 0.9300 . ?
C28 C29 1.365(4) . ?
C28 C33 1.380(4) . ?
C29 C30 1.382(4) . ?
C29 H29A 0.9300 . ?
C30 C31 1.356(4) . ?
C30 H30A 0.9300 . ?
C31 C32 1.367(4) . ?
C31 H31A 0.9300 . ?
C32 C33 1.374(4) . ?
C32 H32A 0.9300 . ?
C33 H33A 0.9300 . ?
C3 C8 1.381(4) . ?
C3 C4 1.384(4) . ?
C4 C5 1.371(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.383(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.381(4) . ?
C6 C9 1.462(4) . ?
C7 C8 1.379(4) . ?
C7 H7A 0.9300 . ?
C8 H8A 0.9300 . ?
C15 C14 1.387(4) . ?
C15 C10 1.393(4) . ?
C14 C13 1.370(4) . ?
C14 H14A 0.9300 . ?
C13 C12 1.385(4) . ?
C13 H13A 0.9300 . ?
C12 C11 1.366(4) . ?
C12 H12A 0.9300 . ?
C11 C10 1.394(4) . ?
C11 H11A 0.9300 . ?
C16 C21 1.368(4) . ?
C16 C17 1.382(4) . ?
C17 C18 1.379(4) . ?
C17 H17A 0.9300 . ?
C18 C19 1.363(5) . ?
C18 H18A 0.9300 . ?
C19 C20 1.361(5) . ?
C19 H19A 0.9300 . ?
C20 C21 1.376(4) . ?
C20 H20A 0.9300 . ?
C21 H21A 0.9300 . ?
N5 C70 1.166(8) . ?
C70 C69 1.399(8) . ?
C69 H69A 0.9600 . ?
C69 H69B 0.9600 . ?
C69 H69C 0.9600 . ?
N6 C72 1.202(12) . ?
C73 C72 1.502(11) . ?
C73 H73A 0.9600 . ?
C73 H73B 0.9600 . ?
C73 H73C 0.9600 . ?
C68 N7 1.172(13) . ?
C68 C67 1.382(12) . ?
C67 H67A 0.9600 . ?
C67 H67B 0.9600 . ?
C67 H67C 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
C60 N3 C66 107.7(3) . . ?
C60 N3 H2 121.7(17) . . ?
C66 N3 H2 130.4(17) . . ?
C60 N4 C61 104.7(2) . . ?
C35 C34 C36 123.7(3) . . ?
C35 C34 C54 121.4(3) . . ?
C36 C34 C54 114.7(2) . . ?
C53 C48 C49 118.3(4) . . ?
C53 C48 C35 121.1(4) . . ?
C49 C48 C35 120.5(4) . . ?
C48 C53 C52 121.2(4) . . ?
C48 C53 H53A 119.4 . . ?
C52 C53 H53A 119.4 . . ?
C51 C52 C53 119.6(5) . . ?
C51 C52 H52A 120.2 . . ?
C53 C52 H52A 120.2 . . ?
C52 C51 C50 120.6(5) . . ?
C52 C51 H51A 119.7 . . ?
C50 C51 H51A 119.7 . . ?
C51 C50 C49 119.7(5) . . ?
C51 C50 H50A 120.2 . . ?
C49 C50 H50A 120.2 . . ?
C48 C49 C50 120.5(4) . . ?
C48 C49 H49A 119.7 . . ?
C50 C49 H49A 119.7 . . ?
C34 C35 C42 123.6(3) . . ?
C34 C35 C48 121.2(3) . . ?
C42 C35 C48 115.2(3) . . ?
C47 C42 C43 117.2(3) . . ?
C47 C42 C35 120.6(3) . . ?
C43 C42 C35 122.0(3) . . ?
C42 C47 C46 120.8(4) . . ?
C42 C47 H47A 119.6 . . ?
C46 C47 H47A 119.6 . . ?
C45 C46 C47 120.5(4) . . ?
C45 C46 H46A 119.8 . . ?
C47 C46 H46A 119.8 . . ?
C44 C45 C46 119.6(4) . . ?
C44 C45 H45A 120.2 . . ?
C46 C45 H45A 120.2 . . ?
C45 C44 C43 120.1(4) . . ?
C45 C44 H44A 119.9 . . ?
C43 C44 H44A 119.9 . . ?
C44 C43 C42 121.7(3) . . ?
C44 C43 H43A 119.1 . . ?
C42 C43 H43A 119.1 . . ?
C41 C36 C37 117.7(3) . . ?
C41 C36 C34 122.4(3) . . ?
C37 C36 C34 119.8(3) . . ?
C36 C41 C40 120.5(4) . . ?
C36 C41 H41A 119.8 . . ?
C40 C41 H41A 119.8 . . ?
C39 C40 C41 118.6(4) . . ?
C39 C40 H40A 120.7 . . ?
C41 C40 H40A 120.7 . . ?
C40 C39 C38 123.1(5) . . ?
C40 C39 H39A 118.5 . . ?
C38 C39 H39A 118.5 . . ?
C37 C38 C39 117.7(5) . . ?
C37 C38 H38A 121.1 . . ?
C39 C38 H38A 121.1 . . ?
C38 C37 C36 122.3(4) . . ?
C38 C37 H37A 118.8 . . ?
C36 C37 H37A 118.8 . . ?
C55 C54 C59 117.2(3) . . ?
C55 C54 C34 119.6(3) . . ?
C59 C54 C34 122.8(3) . . ?
C58 C59 C54 121.6(3) . . ?
C58 C59 H59A 119.2 . . ?
C54 C59 H59A 119.2 . . ?
C59 C58 C57 120.9(3) . . ?
C59 C58 H58A 119.5 . . ?
C57 C58 H58A 119.5 . . ?
C56 C57 C58 117.7(3) . . ?
C56 C57 C60 120.3(3) . . ?
C58 C57 C60 122.0(3) . . ?
C55 C56 C57 121.1(3) . . ?
C55 C56 H56A 119.5 . . ?
C57 C56 H56A 119.5 . . ?
C56 C55 C54 121.4(3) . . ?
C56 C55 H55A 119.3 . . ?
C54 C55 H55A 119.3 . . ?
N4 C60 N3 112.3(3) . . ?
N4 C60 C57 125.1(3) . . ?
N3 C60 C57 122.6(3) . . ?
N3 C66 C65 132.1(3) . . ?
N3 C66 C61 105.3(3) . . ?
C65 C66 C61 122.6(3) . . ?
C64 C65 C66 116.4(3) . . ?
C64 C65 H65A 121.8 . . ?
C66 C65 H65A 121.8 . . ?
C65 C64 C63 121.7(3) . . ?
C65 C64 H64A 119.2 . . ?
C63 C64 H64A 119.2 . . ?
C62 C63 C64 121.3(3) . . ?
C62 C63 H63A 119.4 . . ?
C64 C63 H63A 119.4 . . ?
C63 C62 C61 118.2(3) . . ?
C63 C62 H62A 120.9 . . ?
C61 C62 H62A 120.9 . . ?
C62 C61 C66 119.8(3) . . ?
C62 C61 N4 130.1(3) . . ?
C66 C61 N4 110.0(3) . . ?
C9 N1 C10 106.5(3) . . ?
C9 N1 H1 129.1(17) . . ?
C10 N1 H1 123.8(17) . . ?
C9 N2 C15 105.2(2) . . ?
C1 C2 C22 123.2(3) . . ?
C1 C2 C16 123.1(3) . . ?
C22 C2 C16 113.7(2) . . ?
C2 C1 C28 123.4(2) . . ?
C2 C1 C3 122.5(3) . . ?
C28 C1 C3 114.1(2) . . ?
C27 C22 C23 117.8(3) . . ?
C27 C22 C2 122.2(3) . . ?
C23 C22 C2 120.0(3) . . ?
C24 C23 C22 120.9(3) . . ?
C24 C23 H23A 119.6 . . ?
C22 C23 H23A 119.6 . . ?
C23 C24 C25 120.2(4) . . ?
C23 C24 H24A 119.9 . . ?
C25 C24 H24A 119.9 . . ?
C26 C25 C24 120.1(4) . . ?
C26 C25 H25A 120.0 . . ?
C24 C25 H25A 120.0 . . ?
C25 C26 C27 120.0(4) . . ?
C25 C26 H26A 120.0 . . ?
C27 C26 H26A 120.0 . . ?
C26 C27 C22 121.1(3) . . ?
C26 C27 H27A 119.5 . . ?
C22 C27 H27A 119.5 . . ?
C29 C28 C33 118.0(3) . . ?
C29 C28 C1 122.4(3) . . ?
C33 C28 C1 119.6(3) . . ?
C28 C29 C30 120.9(3) . . ?
C28 C29 H29A 119.6 . . ?
C30 C29 H29A 119.6 . . ?
C31 C30 C29 120.6(3) . . ?
C31 C30 H30A 119.7 . . ?
C29 C30 H30A 119.7 . . ?
C30 C31 C32 119.2(3) . . ?
C30 C31 H31A 120.4 . . ?
C32 C31 H31A 120.4 . . ?
C31 C32 C33 120.3(3) . . ?
C31 C32 H32A 119.8 . . ?
C33 C32 H32A 119.8 . . ?
C32 C33 C28 120.9(3) . . ?
C32 C33 H33A 119.5 . . ?
C28 C33 H33A 119.5 . . ?
C8 C3 C4 117.6(3) . . ?
C8 C3 C1 122.1(3) . . ?
C4 C3 C1 120.0(3) . . ?
C5 C4 C3 121.3(3) . . ?
C5 C4 H4A 119.3 . . ?
C3 C4 H4A 119.3 . . ?
C4 C5 C6 121.2(3) . . ?
C4 C5 H5A 119.4 . . ?
C6 C5 H5A 119.4 . . ?
C5 C6 C7 117.5(3) . . ?
C5 C6 C9 120.2(3) . . ?
C7 C6 C9 122.4(3) . . ?
C8 C7 C6 121.4(3) . . ?
C8 C7 H7A 119.3 . . ?
C6 C7 H7A 119.3 . . ?
C7 C8 C3 120.9(3) . . ?
C7 C8 H8A 119.5 . . ?
C3 C8 H8A 119.5 . . ?
N2 C9 N1 112.7(3) . . ?
N2 C9 C6 123.6(3) . . ?
N1 C9 C6 123.7(3) . . ?
N2 C15 C14 130.1(3) . . ?
N2 C15 C10 109.4(2) . . ?
C14 C15 C10 120.5(3) . . ?
C13 C14 C15 117.9(3) . . ?
C13 C14 H14A 121.1 . . ?
C15 C14 H14A 121.1 . . ?
C14 C13 C12 120.9(3) . . ?
C14 C13 H13A 119.5 . . ?
C12 C13 H13A 119.5 . . ?
C11 C12 C13 122.7(3) . . ?
C11 C12 H12A 118.6 . . ?
C13 C12 H12A 118.6 . . ?
C12 C11 C10 116.3(3) . . ?
C12 C11 H11A 121.8 . . ?
C10 C11 H11A 121.8 . . ?
N1 C10 C15 106.3(3) . . ?
N1 C10 C11 132.1(3) . . ?
C15 C10 C11 121.6(3) . . ?
C21 C16 C17 117.7(3) . . ?
C21 C16 C2 120.3(3) . . ?
C17 C16 C2 121.8(3) . . ?
C18 C17 C16 120.4(4) . . ?
C18 C17 H17A 119.8 . . ?
C16 C17 H17A 119.8 . . ?
C19 C18 C17 120.6(4) . . ?
C19 C18 H18A 119.7 . . ?
C17 C18 H18A 119.7 . . ?
C18 C19 C20 119.7(4) . . ?
C18 C19 H19A 120.2 . . ?
C20 C19 H19A 120.2 . . ?
C19 C20 C21 119.7(4) . . ?
C19 C20 H20A 120.2 . . ?
C21 C20 H20A 120.2 . . ?
C16 C21 C20 121.9(4) . . ?
C16 C21 H21A 119.1 . . ?
C20 C21 H21A 119.1 . . ?
N5 C70 C69 171.8(11) . . ?
C70 C69 H69A 109.5 . . ?
C70 C69 H69B 109.5 . . ?
H69A C69 H69B 109.5 . . ?
C70 C69 H69C 109.5 . . ?
H69A C69 H69C 109.5 . . ?
H69B C69 H69C 109.5 . . ?
C72 C73 H73A 109.5 . . ?
C72 C73 H73B 109.5 . . ?
H73A C73 H73B 109.5 . . ?
C72 C73 H73C 109.5 . . ?
H73A C73 H73C 109.5 . . ?
H73B C73 H73C 109.5 . . ?
N7 C68 C67 173.6(12) . . ?
C68 C67 H67A 109.5 . . ?
C68 C67 H67B 109.5 . . ?
H67A C67 H67B 109.5 . . ?
C68 C67 H67C 109.5 . . ?
H67A C67 H67C 109.5 . . ?
H67B C67 H67C 109.5 . . ?
N6 C72 C73 174.8(11) . . ?

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
C49 C48 C53 C52 -1.4(5) . . . . ?
C35 C48 C53 C52 -178.0(3) . . . . ?
C48 C53 C52 C51 0.4(6) . . . . ?
C53 C52 C51 C50 -0.2(7) . . . . ?
C52 C51 C50 C49 1.0(7) . . . . ?
C53 C48 C49 C50 2.3(5) . . . . ?
C35 C48 C49 C50 178.9(3) . . . . ?
C51 C50 C49 C48 -2.1(6) . . . . ?
C36 C34 C35 C42 -10.6(5) . . . . ?
C54 C34 C35 C42 165.0(3) . . . . ?
C36 C34 C35 C48 169.0(3) . . . . ?
C54 C34 C35 C48 -15.4(5) . . . . ?
C53 C48 C35 C34 -54.3(4) . . . . ?
C49 C48 C35 C34 129.2(3) . . . . ?
C53 C48 C35 C42 125.3(3) . . . . ?
C49 C48 C35 C42 -51.2(4) . . . . ?
C34 C35 C42 C47 142.3(3) . . . . ?
C48 C35 C42 C47 -37.3(4) . . . . ?
C34 C35 C42 C43 -42.0(5) . . . . ?
C48 C35 C42 C43 138.4(3) . . . . ?
C43 C42 C47 C46 2.9(5) . . . . ?
C35 C42 C47 C46 178.7(3) . . . . ?
C42 C47 C46 C45 -1.0(6) . . . . ?
C47 C46 C45 C44 -1.0(7) . . . . ?
C46 C45 C44 C43 0.9(6) . . . . ?
C45 C44 C43 C42 1.1(6) . . . . ?
C47 C42 C43 C44 -3.0(5) . . . . ?
C35 C42 C43 C44 -178.7(3) . . . . ?
C35 C34 C36 C41 -50.8(5) . . . . ?
C54 C34 C36 C41 133.3(3) . . . . ?
C35 C34 C36 C37 130.1(3) . . . . ?
C54 C34 C36 C37 -45.8(4) . . . . ?
C37 C36 C41 C40 -1.1(5) . . . . ?
C34 C36 C41 C40 179.8(3) . . . . ?
C36 C41 C40 C39 0.3(6) . . . . ?
C41 C40 C39 C38 0.2(7) . . . . ?
C40 C39 C38 C37 0.1(7) . . . . ?
C39 C38 C37 C36 -1.0(6) . . . . ?
C41 C36 C37 C38 1.5(5) . . . . ?
C34 C36 C37 C38 -179.4(3) . . . . ?
C35 C34 C54 C55 -60.1(4) . . . . ?
C36 C34 C54 C55 115.9(3) . . . . ?
C35 C34 C54 C59 126.7(3) . . . . ?
C36 C34 C54 C59 -57.3(4) . . . . ?
C55 C54 C59 C58 -1.0(4) . . . . ?
C34 C54 C59 C58 172.4(3) . . . . ?
C54 C59 C58 C57 -1.4(4) . . . . ?
C59 C58 C57 C56 3.2(4) . . . . ?
C59 C58 C57 C60 -174.7(3) . . . . ?
C58 C57 C56 C55 -2.5(4) . . . . ?
C60 C57 C56 C55 175.3(2) . . . . ?
C57 C56 C55 C54 0.1(4) . . . . ?
C59 C54 C55 C56 1.7(4) . . . . ?
C34 C54 C55 C56 -171.9(3) . . . . ?
C61 N4 C60 N3 0.9(3) . . . . ?
C61 N4 C60 C57 -179.9(2) . . . . ?
C66 N3 C60 N4 -0.6(3) . . . . ?
C66 N3 C60 C57 -179.9(2) . . . . ?
C56 C57 C60 N4 157.6(3) . . . . ?
C58 C57 C60 N4 -24.6(4) . . . . ?
C56 C57 C60 N3 -23.2(4) . . . . ?
C58 C57 C60 N3 154.6(3) . . . . ?
C60 N3 C66 C65 180.0(3) . . . . ?
C60 N3 C66 C61 0.1(3) . . . . ?
N3 C66 C65 C64 -179.8(3) . . . . ?
C61 C66 C65 C64 0.1(4) . . . . ?
C66 C65 C64 C63 -0.7(5) . . . . ?
C65 C64 C63 C62 0.7(5) . . . . ?
C64 C63 C62 C61 0.0(5) . . . . ?
C63 C62 C61 C66 -0.6(4) . . . . ?
C63 C62 C61 N4 179.5(3) . . . . ?
N3 C66 C61 C62 -179.5(2) . . . . ?
C65 C66 C61 C62 0.6(4) . . . . ?
N3 C66 C61 N4 0.5(3) . . . . ?
C65 C66 C61 N4 -179.4(2) . . . . ?
C60 N4 C61 C62 179.2(3) . . . . ?
C60 N4 C61 C66 -0.8(3) . . . . ?
C22 C2 C1 C28 7.2(5) . . . . ?
C16 C2 C1 C28 -173.0(3) . . . . ?
C22 C2 C1 C3 -172.6(3) . . . . ?
C16 C2 C1 C3 7.2(4) . . . . ?
C1 C2 C22 C27 57.7(4) . . . . ?
C16 C2 C22 C27 -122.2(3) . . . . ?
C1 C2 C22 C23 -124.7(3) . . . . ?
C16 C2 C22 C23 55.5(4) . . . . ?
C27 C22 C23 C24 -0.5(5) . . . . ?
C2 C22 C23 C24 -178.2(3) . . . . ?
C22 C23 C24 C25 0.6(5) . . . . ?
C23 C24 C25 C26 -0.1(6) . . . . ?
C24 C25 C26 C27 -0.5(6) . . . . ?
C25 C26 C27 C22 0.6(6) . . . . ?
C23 C22 C27 C26 -0.1(5) . . . . ?
C2 C22 C27 C26 177.6(3) . . . . ?
C2 C1 C28 C29 49.1(4) . . . . ?
C3 C1 C28 C29 -131.1(3) . . . . ?
C2 C1 C28 C33 -133.4(3) . . . . ?
C3 C1 C28 C33 46.4(4) . . . . ?
C33 C28 C29 C30 0.8(4) . . . . ?
C1 C28 C29 C30 178.4(3) . . . . ?
C28 C29 C30 C31 0.3(5) . . . . ?
C29 C30 C31 C32 -0.6(5) . . . . ?
C30 C31 C32 C33 -0.1(5) . . . . ?
C31 C32 C33 C28 1.1(5) . . . . ?
C29 C28 C33 C32 -1.5(4) . . . . ?
C1 C28 C33 C32 -179.1(3) . . . . ?
C2 C1 C3 C8 56.3(4) . . . . ?
C28 C1 C3 C8 -123.5(3) . . . . ?
C2 C1 C3 C4 -129.1(3) . . . . ?
C28 C1 C3 C4 51.0(3) . . . . ?
C8 C3 C4 C5 -0.9(4) . . . . ?
C1 C3 C4 C5 -175.7(3) . . . . ?
C3 C4 C5 C6 1.6(4) . . . . ?
C4 C5 C6 C7 -1.1(4) . . . . ?
C4 C5 C6 C9 179.6(2) . . . . ?
C5 C6 C7 C8 0.1(4) . . . . ?
C9 C6 C7 C8 179.4(2) . . . . ?
C6 C7 C8 C3 0.5(4) . . . . ?
C4 C3 C8 C7 -0.1(4) . . . . ?
C1 C3 C8 C7 174.6(2) . . . . ?
C15 N2 C9 N1 -0.8(3) . . . . ?
C15 N2 C9 C6 179.5(2) . . . . ?
C10 N1 C9 N2 0.3(3) . . . . ?
C10 N1 C9 C6 180.0(2) . . . . ?
C5 C6 C9 N2 5.4(4) . . . . ?
C7 C6 C9 N2 -173.8(2) . . . . ?
C5 C6 C9 N1 -174.2(2) . . . . ?
C7 C6 C9 N1 6.6(4) . . . . ?
C9 N2 C15 C14 -179.0(3) . . . . ?
C9 N2 C15 C10 1.0(3) . . . . ?
N2 C15 C14 C13 -179.2(3) . . . . ?
C10 C15 C14 C13 0.8(4) . . . . ?
C15 C14 C13 C12 -0.3(5) . . . . ?
C14 C13 C12 C11 0.0(5) . . . . ?
C13 C12 C11 C10 -0.2(5) . . . . ?
C9 N1 C10 C15 0.3(3) . . . . ?
C9 N1 C10 C11 -179.4(3) . . . . ?
N2 C15 C10 N1 -0.8(3) . . . . ?
C14 C15 C10 N1 179.2(2) . . . . ?
N2 C15 C10 C11 179.0(2) . . . . ?
C14 C15 C10 C11 -1.0(4) . . . . ?
C12 C11 C10 N1 -179.6(3) . . . . ?
C12 C11 C10 C15 0.7(4) . . . . ?
C1 C2 C16 C21 -124.6(3) . . . . ?
C22 C2 C16 C21 55.2(4) . . . . ?
C1 C2 C16 C17 59.6(4) . . . . ?
C22 C2 C16 C17 -120.5(3) . . . . ?
C21 C16 C17 C18 0.6(5) . . . . ?
C2 C16 C17 C18 176.5(3) . . . . ?
C16 C17 C18 C19 0.0(5) . . . . ?
C17 C18 C19 C20 0.3(6) . . . . ?
C18 C19 C20 C21 -1.2(6) . . . . ?
C17 C16 C21 C20 -1.6(5) . . . . ?
C2 C16 C21 C20 -177.5(3) . . . . ?
C19 C20 C21 C16 1.8(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.037
####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1478705'
_audit_update_record             
;
2016-05-09 deposited with the CCDC.
2016-08-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H23 Br2 N2 O0.50'
_chemical_formula_weight         615.35

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'
Br Br -0.2901 2.4595 '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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 2'

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

_cell_length_a                   9.581(3)
_cell_length_b                   35.690(12)
_cell_length_c                   9.867(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3374.0(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2436
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      26.32

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1236
_exptl_absorpt_coefficient_mu    2.424
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.814
_exptl_absorpt_correction_T_max  0.856
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX II CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            17206
_diffrn_reflns_av_R_equivalents  0.1032
_diffrn_reflns_av_sigmaI/netI    0.1442
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.41
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5908
_reflns_number_gt                2805
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_reduction        SAINT-Plus
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XP (Sheldrick, 1998)'
_computing_publication_material  XP

_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)+(0.0839P)²+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.01(2)
_refine_ls_number_reflns         5908
_refine_ls_number_parameters     337
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1745
_refine_ls_R_factor_gt           0.0728
_refine_ls_wR_factor_ref         0.1921
_refine_ls_wR_factor_gt          0.1687
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_restrained_S_all      0.991
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.63759(12) -0.16188(3) 0.77910(11) 0.0819(4) Uani 1 1 d . . .
Br2 Br 0.79401(14) -0.16121(3) 0.47875(13) 0.0983(5) Uani 1 1 d . . .
N1 N 0.8020(8) -0.01384(19) 0.5536(8) 0.064(2) Uani 1 1 d . . .
H1 H 0.8448 -0.0051 0.4837 0.077 Uiso 1 1 calc R . .
N2 N 0.6912(9) -0.01479(18) 0.7480(7) 0.065(2) Uani 1 1 d . . .
C1 C 0.7492(10) 0.0058(3) 0.6557(10) 0.060(3) Uani 1 1 d . . .
C2 C 0.7632(11) 0.0473(2) 0.6589(9) 0.061(3) Uani 1 1 d . . .
C3 C 0.8341(10) 0.0676(2) 0.5671(9) 0.064(3) Uani 1 1 d . . .
H3 H 0.8780 0.0555 0.4954 0.076 Uiso 1 1 calc R . .
C4 C 0.8428(10) 0.1055(2) 0.5773(9) 0.057(3) Uani 1 1 d . . .
H4 H 0.8899 0.1186 0.5099 0.068 Uiso 1 1 calc R . .
C5 C 0.7851(9) 0.1251(2) 0.6825(9) 0.045(2) Uani 1 1 d . . .
C6 C 0.7076(10) 0.1045(2) 0.7743(9) 0.055(2) Uani 1 1 d . . .
H6 H 0.6614 0.1166 0.8446 0.065 Uiso 1 1 calc R . .
C7 C 0.6982(11) 0.0661(2) 0.7628(10) 0.070(3) Uani 1 1 d . . .
H7 H 0.6470 0.0526 0.8264 0.084 Uiso 1 1 calc R . .
C8 C 0.7967(8) 0.1656(2) 0.6983(7) 0.0425(19) Uani 1 1 d . . .
C9 C 0.8321(8) 0.1820(2) 0.8159(8) 0.040(2) Uani 1 1 d . . .
C10 C 0.8859(8) 0.1612(2) 0.9320(8) 0.0441(19) Uani 1 1 d . . .
C11 C 0.8360(10) 0.1669(2) 1.0610(10) 0.060(2) Uani 1 1 d . . .
H11 H 0.7629 0.1838 1.0723 0.072 Uiso 1 1 calc R . .
C12 C 0.8863(13) 0.1496(3) 1.1721(11) 0.077(3) Uani 1 1 d . . .
H12 H 0.8507 0.1550 1.2576 0.092 Uiso 1 1 calc R . .
C13 C 0.9919(14) 0.1237(4) 1.1559(13) 0.096(4) Uani 1 1 d U . .
H13 H 1.0249 0.1102 1.2299 0.115 Uiso 1 1 calc R . .
C14 C 1.0498(12) 0.1178(4) 1.0248(13) 0.093(4) Uani 1 1 d . . .
H14 H 1.1257 0.1019 1.0128 0.112 Uiso 1 1 calc R . .
C15 C 0.9913(7) 0.13616(18) 0.9167(7) 0.067(3) Uani 1 1 d . . .
H15 H 1.0249 0.1313 0.8301 0.080 Uiso 1 1 calc R . .
C16 C 0.8148(7) 0.22378(18) 0.8391(7) 0.047(2) Uani 1 1 d R . .
C17 C 0.9237(10) 0.2435(2) 0.9016(9) 0.053(2) Uani 1 1 d . . .
H17 H 1.0050 0.2313 0.9284 0.064 Uiso 1 1 calc R . .
C18 C 0.9067(12) 0.2814(2) 0.9221(10) 0.060(3) Uani 1 1 d . . .
H18 H 0.9779 0.2948 0.9637 0.072 Uiso 1 1 calc R . .
C19 C 0.7904(15) 0.2995(3) 0.8837(10) 0.070(3) Uani 1 1 d . . .
H19 H 0.7816 0.3253 0.8955 0.084 Uiso 1 1 calc R . .
C20 C 0.6860(13) 0.2791(3) 0.8271(9) 0.068(3) Uani 1 1 d . . .
H20 H 0.6032 0.2912 0.8046 0.082 Uiso 1 1 calc R . .
C21 C 0.6961(10) 0.2430(2) 0.8025(9) 0.057(2) Uani 1 1 d . . .
H21 H 0.6229 0.2304 0.7604 0.068 Uiso 1 1 calc R . .
C22 C 0.7689(10) 0.1888(2) 0.5715(9) 0.042(2) Uani 1 1 d . . .
C23 C 0.6480(12) 0.1841(3) 0.4975(10) 0.066(3) Uani 1 1 d . . .
H23 H 0.5835 0.1660 0.5235 0.079 Uiso 1 1 calc R . .
C24 C 0.6227(12) 0.2057(3) 0.3873(10) 0.062(3) Uani 1 1 d . . .
H24 H 0.5413 0.2019 0.3377 0.075 Uiso 1 1 calc R . .
C25 C 0.7131(14) 0.2325(3) 0.3480(10) 0.068(3) Uani 1 1 d . . .
H25 H 0.6929 0.2475 0.2736 0.082 Uiso 1 1 calc R . .
C26 C 0.8317(12) 0.2372(2) 0.4167(11) 0.063(3) Uani 1 1 d . . .
H26 H 0.8948 0.2555 0.3889 0.076 Uiso 1 1 calc R . .
C27 C 0.8623(11) 0.2155(2) 0.5283(10) 0.060(3) Uani 1 1 d . . .
H27 H 0.9461 0.2188 0.5743 0.072 Uiso 1 1 calc R . .
C28 C 0.7048(10) -0.0506(2) 0.7063(9) 0.053(2) Uani 1 1 d . . .
C29 C 0.7745(10) -0.0509(2) 0.5819(11) 0.061(3) Uani 1 1 d . . .
C30 C 0.8012(10) -0.0834(2) 0.5168(10) 0.066(3) Uani 1 1 d . . .
H30 H 0.8476 -0.0832 0.4340 0.080 Uiso 1 1 calc R . .
C31 C 0.7601(9) -0.1163(3) 0.5724(11) 0.059(3) Uani 1 1 d . . .
C32 C 0.6892(11) -0.1162(2) 0.6928(11) 0.063(3) Uani 1 1 d . . .
C33 C 0.6642(10) -0.0842(3) 0.7628(10) 0.067(3) Uani 1 1 d . . .
H33 H 0.6206 -0.0849 0.8469 0.080 Uiso 1 1 calc R . .
O1 O 0.5000 0.0000 0.9518(9) 0.088(3) Uani 1 2 d S . .
H1W H 0.5872 0.0005 0.9064 0.131 Uiso 1 1 d R . .


_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
Br1 C32 1.906(9) . ?
Br2 C31 1.877(9) . ?
N1 C1 1.328(10) . ?
N1 C29 1.376(10) . ?
N1 H1 0.8600 . ?
N2 C1 1.295(11) . ?
N2 C28 1.348(9) . ?
C1 C2 1.487(12) . ?
C2 C3 1.344(12) . ?
C2 C7 1.374(12) . ?
C3 C4 1.359(11) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(11) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(11) . ?
C5 C8 1.456(11) . ?
C6 C7 1.378(11) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.343(10) . ?
C8 C22 1.525(11) . ?
C9 C10 1.460(11) . ?
C9 C16 1.518(10) . ?
C10 C15 1.356(10) . ?
C10 C11 1.375(12) . ?
C11 C12 1.347(13) . ?
C11 H11 0.9300 . ?
C12 C13 1.379(16) . ?
C12 H12 0.9300 . ?
C13 C14 1.423(16) . ?
C13 H13 0.9300 . ?
C14 C15 1.372(13) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C21 1.377(11) . ?
C16 C17 1.401(10) . ?
C17 C18 1.378(12) . ?
C17 H17 0.9300 . ?
C18 C19 1.343(13) . ?
C18 H18 0.9300 . ?
C19 C20 1.359(14) . ?
C19 H19 0.9300 . ?
C20 C21 1.312(12) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C27 1.373(12) . ?
C22 C23 1.379(12) . ?
C23 C24 1.355(12) . ?
C23 H23 0.9300 . ?
C24 C25 1.347(14) . ?
C24 H24 0.9300 . ?
C25 C26 1.335(14) . ?
C25 H25 0.9300 . ?
C26 C27 1.379(13) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 C33 1.378(11) . ?
C28 C29 1.398(13) . ?
C29 C30 1.351(12) . ?
C30 C31 1.356(12) . ?
C30 H30 0.9300 . ?
C31 C32 1.368(13) . ?
C32 C33 1.355(12) . ?
C33 H33 0.9300 . ?
O1 H1W 0.9479 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C29 106.3(8) . . ?
C1 N1 H1 126.9 . . ?
C29 N1 H1 126.9 . . ?
C1 N2 C28 106.4(8) . . ?
N2 C1 N1 113.4(8) . . ?
N2 C1 C2 126.1(8) . . ?
N1 C1 C2 120.5(9) . . ?
C3 C2 C7 117.9(8) . . ?
C3 C2 C1 124.6(8) . . ?
C7 C2 C1 117.5(8) . . ?
C2 C3 C4 121.2(8) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 122.7(8) . . ?
C3 C4 H4 118.6 . . ?
C5 C4 H4 118.6 . . ?
C4 C5 C6 116.1(7) . . ?
C4 C5 C8 123.9(8) . . ?
C6 C5 C8 119.9(7) . . ?
C7 C6 C5 120.7(8) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C2 C7 C6 121.2(9) . . ?
C2 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C9 C8 C5 122.9(7) . . ?
C9 C8 C22 121.1(7) . . ?
C5 C8 C22 116.0(7) . . ?
C8 C9 C10 123.1(7) . . ?
C8 C9 C16 122.1(7) . . ?
C10 C9 C16 114.8(7) . . ?
C15 C10 C11 117.4(8) . . ?
C15 C10 C9 120.7(7) . . ?
C11 C10 C9 121.9(8) . . ?
C12 C11 C10 124.1(9) . . ?
C12 C11 H11 118.0 . . ?
C10 C11 H11 118.0 . . ?
C11 C12 C13 118.4(11) . . ?
C11 C12 H12 120.8 . . ?
C13 C12 H12 120.8 . . ?
C12 C13 C14 119.4(11) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C15 C14 C13 118.5(11) . . ?
C15 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?
C10 C15 C14 122.1(8) . . ?
C10 C15 H15 118.9 . . ?
C14 C15 H15 118.9 . . ?
C21 C16 C17 118.7(7) . . ?
C21 C16 C9 122.7(7) . . ?
C17 C16 C9 118.5(6) . . ?
C18 C17 C16 118.0(9) . . ?
C18 C17 H17 121.0 . . ?
C16 C17 H17 121.0 . . ?
C19 C18 C17 122.0(9) . . ?
C19 C18 H18 119.0 . . ?
C17 C18 H18 119.0 . . ?
C18 C19 C20 117.9(9) . . ?
C18 C19 H19 121.1 . . ?
C20 C19 H19 121.1 . . ?
C21 C20 C19 123.2(10) . . ?
C21 C20 H20 118.4 . . ?
C19 C20 H20 118.4 . . ?
C20 C21 C16 120.1(9) . . ?
C20 C21 H21 119.9 . . ?
C16 C21 H21 119.9 . . ?
C27 C22 C23 117.9(8) . . ?
C27 C22 C8 121.1(8) . . ?
C23 C22 C8 120.9(8) . . ?
C24 C23 C22 120.4(9) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C25 C24 C23 121.3(10) . . ?
C25 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?
C26 C25 C24 119.5(9) . . ?
C26 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
C25 C26 C27 121.0(9) . . ?
C25 C26 H26 119.5 . . ?
C27 C26 H26 119.5 . . ?
C22 C27 C26 120.0(9) . . ?
C22 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
N2 C28 C33 132.4(9) . . ?
N2 C28 C29 108.7(7) . . ?
C33 C28 C29 118.9(8) . . ?
C30 C29 N1 133.8(10) . . ?
C30 C29 C28 120.9(8) . . ?
N1 C29 C28 105.2(8) . . ?
C29 C30 C31 119.9(10) . . ?
C29 C30 H30 120.1 . . ?
C31 C30 H30 120.1 . . ?
C30 C31 C32 119.4(9) . . ?
C30 C31 Br2 119.4(8) . . ?
C32 C31 Br2 121.2(7) . . ?
C33 C32 C31 122.3(9) . . ?
C33 C32 Br1 116.6(8) . . ?
C31 C32 Br1 120.8(7) . . ?
C32 C33 C28 118.5(9) . . ?
C32 C33 H33 120.8 . . ?
C28 C33 H33 120.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C28 N2 C1 N1 -0.2(11) . . . . ?
C28 N2 C1 C2 -178.3(9) . . . . ?
C29 N1 C1 N2 0.5(11) . . . . ?
C29 N1 C1 C2 178.8(8) . . . . ?
N2 C1 C2 C3 174.2(10) . . . . ?
N1 C1 C2 C3 -3.8(15) . . . . ?
N2 C1 C2 C7 -6.2(15) . . . . ?
N1 C1 C2 C7 175.8(9) . . . . ?
C7 C2 C3 C4 0.7(15) . . . . ?
C1 C2 C3 C4 -179.7(10) . . . . ?
C2 C3 C4 C5 2.3(16) . . . . ?
C3 C4 C5 C6 -4.6(14) . . . . ?
C3 C4 C5 C8 177.9(9) . . . . ?
C4 C5 C6 C7 4.0(14) . . . . ?
C8 C5 C6 C7 -178.5(9) . . . . ?
C3 C2 C7 C6 -1.3(15) . . . . ?
C1 C2 C7 C6 179.1(10) . . . . ?
C5 C6 C7 C2 -1.1(16) . . . . ?
C4 C5 C8 C9 -132.8(9) . . . . ?
C6 C5 C8 C9 49.8(12) . . . . ?
C4 C5 C8 C22 46.0(12) . . . . ?
C6 C5 C8 C22 -131.3(8) . . . . ?
C5 C8 C9 C10 11.1(13) . . . . ?
C22 C8 C9 C10 -167.7(7) . . . . ?
C5 C8 C9 C16 -167.1(7) . . . . ?
C22 C8 C9 C16 14.2(12) . . . . ?
C8 C9 C10 C15 48.9(11) . . . . ?
C16 C9 C10 C15 -132.8(8) . . . . ?
C8 C9 C10 C11 -133.3(9) . . . . ?
C16 C9 C10 C11 44.9(11) . . . . ?
C15 C10 C11 C12 0.8(13) . . . . ?
C9 C10 C11 C12 -177.0(9) . . . . ?
C10 C11 C12 C13 -1.8(16) . . . . ?
C11 C12 C13 C14 3.8(17) . . . . ?
C12 C13 C14 C15 -4.8(17) . . . . ?
C11 C10 C15 C14 -1.8(13) . . . . ?
C9 C10 C15 C14 176.0(9) . . . . ?
C13 C14 C15 C10 3.8(15) . . . . ?
C8 C9 C16 C21 44.9(11) . . . . ?
C10 C9 C16 C21 -133.3(8) . . . . ?
C8 C9 C16 C17 -135.7(8) . . . . ?
C10 C9 C16 C17 46.0(9) . . . . ?
C21 C16 C17 C18 -0.7(12) . . . . ?
C9 C16 C17 C18 180.0(8) . . . . ?
C16 C17 C18 C19 -0.2(14) . . . . ?
C17 C18 C19 C20 2.1(15) . . . . ?
C18 C19 C20 C21 -3.3(15) . . . . ?
C19 C20 C21 C16 2.5(15) . . . . ?
C17 C16 C21 C20 -0.4(13) . . . . ?
C9 C16 C21 C20 178.9(8) . . . . ?
C9 C8 C22 C27 50.6(11) . . . . ?
C5 C8 C22 C27 -128.2(8) . . . . ?
C9 C8 C22 C23 -128.5(9) . . . . ?
C5 C8 C22 C23 52.7(11) . . . . ?
C27 C22 C23 C24 -1.0(13) . . . . ?
C8 C22 C23 C24 178.1(8) . . . . ?
C22 C23 C24 C25 -0.9(14) . . . . ?
C23 C24 C25 C26 1.8(15) . . . . ?
C24 C25 C26 C27 -0.9(15) . . . . ?
C23 C22 C27 C26 2.0(12) . . . . ?
C8 C22 C27 C26 -177.2(7) . . . . ?
C25 C26 C27 C22 -1.0(14) . . . . ?
C1 N2 C28 C33 179.6(10) . . . . ?
C1 N2 C28 C29 -0.2(11) . . . . ?
C1 N1 C29 C30 179.5(10) . . . . ?
C1 N1 C29 C28 -0.6(10) . . . . ?
N2 C28 C29 C30 -179.6(9) . . . . ?
C33 C28 C29 C30 0.5(14) . . . . ?
N2 C28 C29 N1 0.5(10) . . . . ?
C33 C28 C29 N1 -179.4(8) . . . . ?
N1 C29 C30 C31 179.8(10) . . . . ?
C28 C29 C30 C31 -0.1(15) . . . . ?
C29 C30 C31 C32 1.4(14) . . . . ?
C29 C30 C31 Br2 178.5(7) . . . . ?
C30 C31 C32 C33 -3.4(15) . . . . ?
Br2 C31 C32 C33 179.6(7) . . . . ?
C30 C31 C32 Br1 -176.9(7) . . . . ?
Br2 C31 C32 Br1 6.1(11) . . . . ?
C31 C32 C33 C28 3.8(15) . . . . ?
Br1 C32 C33 C28 177.6(7) . . . . ?
N2 C28 C33 C32 177.8(10) . . . . ?
C29 C28 C33 C32 -2.3(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.823
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.100
####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1478706'
_audit_update_record             
;
2016-05-09 deposited with the CCDC.
2016-08-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H24 Cl2 N2 O'
_chemical_formula_weight         535.44

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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                   26.19(3)
_cell_length_b                   9.313(10)
_cell_length_c                   11.122(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.79(2)
_cell_angle_gamma                90.00
_cell_volume                     2656(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2436
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      26.32

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1112
_exptl_absorpt_coefficient_mu    0.274
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.814
_exptl_absorpt_correction_T_max  0.856
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX II CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            13270
_diffrn_reflns_av_R_equivalents  0.0805
_diffrn_reflns_av_sigmaI/netI    0.1156
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4672
_reflns_number_gt                2383
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_reduction        SAINT-Plus
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XP (Sheldrick, 1998)'
_computing_publication_material  XP

_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)+(0.0109P)²+0.0000P] 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         4672
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1290
_refine_ls_R_factor_gt           0.0563
_refine_ls_wR_factor_ref         0.1270
_refine_ls_wR_factor_gt          0.1086
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_restrained_S_all      0.971
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.12579(3) 0.22266(10) 0.53345(9) 0.0739(3) Uani 1 1 d . . .
Cl2 Cl -0.11880(3) -0.00544(10) 0.33157(9) 0.0741(3) Uani 1 1 d . . .
N1 N 0.06496(9) 0.3321(2) 0.5130(2) 0.0479(7) Uani 1 1 d . . .
H1 H 0.0738 0.4017 0.5639 0.057 Uiso 1 1 calc R . .
N2 N 0.07078(10) 0.1674(3) 0.3742(2) 0.0485(7) Uani 1 1 d . . .
C1 C 0.09601(12) 0.2680(3) 0.4457(3) 0.0456(8) Uani 1 1 d . . .
C2 C 0.15028(11) 0.3035(3) 0.4559(3) 0.0429(8) Uani 1 1 d . . .
C3 C 0.17408(13) 0.4078(3) 0.5362(3) 0.0582(10) Uani 1 1 d . . .
H3 H 0.1548 0.4582 0.5838 0.070 Uiso 1 1 calc R . .
C4 C 0.22565(13) 0.4371(3) 0.5459(3) 0.0573(9) Uani 1 1 d . . .
H4 H 0.2408 0.5096 0.5989 0.069 Uiso 1 1 calc R . .
C5 C 0.25579(11) 0.3637(3) 0.4805(3) 0.0468(9) Uani 1 1 d . . .
C6 C 0.23200(12) 0.2593(3) 0.4010(3) 0.0559(9) Uani 1 1 d . . .
H6 H 0.2516 0.2067 0.3555 0.067 Uiso 1 1 calc R . .
C7 C 0.18014(12) 0.2321(3) 0.3880(3) 0.0545(9) Uani 1 1 d . . .
H7 H 0.1647 0.1632 0.3316 0.065 Uiso 1 1 calc R . .
C8 C 0.31256(12) 0.3925(3) 0.5007(3) 0.0482(9) Uani 1 1 d . . .
C9 C 0.33162(12) 0.5236(3) 0.4902(3) 0.0461(8) Uani 1 1 d . . .
C10 C 0.29689(11) 0.6421(3) 0.4356(3) 0.0467(8) Uani 1 1 d . . .
C11 C 0.29666(12) 0.7691(4) 0.4973(3) 0.0613(10) Uani 1 1 d . . .
H11 H 0.3194 0.7819 0.5725 0.074 Uiso 1 1 calc R . .
C12 C 0.26356(15) 0.8767(4) 0.4499(4) 0.0719(12) Uani 1 1 d . . .
H12 H 0.2628 0.9607 0.4947 0.086 Uiso 1 1 calc R . .
C13 C 0.23158(13) 0.8628(4) 0.3374(4) 0.0656(11) Uani 1 1 d . . .
H13 H 0.2095 0.9375 0.3046 0.079 Uiso 1 1 calc R . .
C14 C 0.23224(13) 0.7394(4) 0.2740(3) 0.0613(10) Uani 1 1 d . . .
H14 H 0.2105 0.7293 0.1971 0.074 Uiso 1 1 calc R . .
C15 C 0.26461(12) 0.6289(3) 0.3220(3) 0.0554(9) Uani 1 1 d . . .
H15 H 0.2648 0.5445 0.2774 0.067 Uiso 1 1 calc R . .
C16 C 0.34593(12) 0.2646(3) 0.5395(3) 0.0491(9) Uani 1 1 d . . .
C17 C 0.33732(13) 0.1822(4) 0.6356(3) 0.0584(10) Uani 1 1 d . . .
H17 H 0.3113 0.2077 0.6774 0.070 Uiso 1 1 calc R . .
C18 C 0.36698(15) 0.0628(4) 0.6701(4) 0.0664(11) Uani 1 1 d . . .
H18 H 0.3615 0.0092 0.7369 0.080 Uiso 1 1 calc R . .
C19 C 0.40374(14) 0.0212(4) 0.6099(4) 0.0685(12) Uani 1 1 d . . .
H19 H 0.4234 -0.0608 0.6343 0.082 Uiso 1 1 calc R . .
C20 C 0.41205(13) 0.0996(4) 0.5133(4) 0.0703(11) Uani 1 1 d . . .
H20 H 0.4374 0.0709 0.4707 0.084 Uiso 1 1 calc R . .
C21 C 0.38314(13) 0.2219(4) 0.4778(3) 0.0626(10) Uani 1 1 d . . .
H21 H 0.3891 0.2754 0.4115 0.075 Uiso 1 1 calc R . .
C22 C 0.38697(12) 0.5626(3) 0.5369(3) 0.0503(9) Uani 1 1 d . . .
C23 C 0.41183(14) 0.5262(4) 0.6542(4) 0.0734(12) Uani 1 1 d . . .
H23 H 0.3942 0.4736 0.7041 0.088 Uiso 1 1 calc R . .
C24 C 0.46258(16) 0.5674(4) 0.6977(4) 0.0887(14) Uani 1 1 d . . .
H24 H 0.4789 0.5430 0.7774 0.106 Uiso 1 1 calc R . .
C25 C 0.48894(15) 0.6417(4) 0.6277(5) 0.0829(13) Uani 1 1 d . . .
H25 H 0.5235 0.6669 0.6581 0.099 Uiso 1 1 calc R . .
C26 C 0.46521(14) 0.6804(4) 0.5124(4) 0.0756(12) Uani 1 1 d . . .
H26 H 0.4833 0.7327 0.4633 0.091 Uiso 1 1 calc R . .
C27 C 0.41407(13) 0.6417(3) 0.4688(4) 0.0617(10) Uani 1 1 d . . .
H27 H 0.3976 0.6705 0.3904 0.074 Uiso 1 1 calc R . .
C28 C 0.01737(12) 0.2679(3) 0.4867(3) 0.0465(8) Uani 1 1 d . . .
C29 C 0.02167(12) 0.1661(3) 0.3974(3) 0.0452(8) Uani 1 1 d . . .
C30 C -0.02107(13) 0.0801(3) 0.3514(3) 0.0520(9) Uani 1 1 d . . .
H30 H -0.0189 0.0099 0.2931 0.062 Uiso 1 1 calc R . .
C31 C -0.06593(12) 0.0990(3) 0.3921(3) 0.0502(9) Uani 1 1 d . . .
C32 C -0.06915(12) 0.2008(4) 0.4816(3) 0.0522(9) Uani 1 1 d . . .
C33 C -0.02744(12) 0.2867(3) 0.5290(3) 0.0521(9) Uani 1 1 d . . .
H33 H -0.0297 0.3558 0.5881 0.063 Uiso 1 1 calc R . .
O1W O 0.08655(9) 0.5246(2) 0.7053(2) 0.0719(7) Uani 1 1 d . . .
H1WA H 0.0946 0.6079 0.7345 0.108 Uiso 1 1 d R . .
H1WB H 0.0893 0.4647 0.7639 0.108 Uiso 1 1 d R . .


_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
Cl1 C32 1.710(4) . ?
Cl2 C31 1.713(3) . ?
N1 C1 1.352(4) . ?
N1 C28 1.359(4) . ?
N1 H1 0.8600 . ?
N2 C1 1.316(4) . ?
N2 C29 1.362(4) . ?
C1 C2 1.441(4) . ?
C2 C7 1.366(4) . ?
C2 C3 1.379(4) . ?
C3 C4 1.360(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.361(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.376(4) . ?
C5 C8 1.482(4) . ?
C6 C7 1.360(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.334(4) . ?
C8 C16 1.488(4) . ?
C9 C10 1.479(4) . ?
C9 C22 1.482(4) . ?
C10 C11 1.368(4) . ?
C10 C15 1.375(4) . ?
C11 C12 1.359(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.362(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.350(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.370(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C21 1.361(5) . ?
C16 C17 1.371(5) . ?
C17 C18 1.366(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.337(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.353(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.380(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C27 1.356(5) . ?
C22 C23 1.377(5) . ?
C23 C24 1.373(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.334(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.355(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.376(4) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 C33 1.361(4) . ?
C28 C29 1.394(4) . ?
C29 C30 1.387(4) . ?
C30 C31 1.354(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.389(5) . ?
C32 C33 1.370(4) . ?
C33 H33 0.9300 . ?
O1W H1WA 0.8499 . ?
O1W H1WB 0.8500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C28 108.4(3) . . ?
C1 N1 H1 125.8 . . ?
C28 N1 H1 125.8 . . ?
C1 N2 C29 105.6(3) . . ?
N2 C1 N1 111.4(3) . . ?
N2 C1 C2 125.2(3) . . ?
N1 C1 C2 123.4(3) . . ?
C7 C2 C3 117.8(3) . . ?
C7 C2 C1 120.8(3) . . ?
C3 C2 C1 121.4(3) . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 122.1(3) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C4 C5 C6 117.6(3) . . ?
C4 C5 C8 120.1(3) . . ?
C6 C5 C8 122.3(3) . . ?
C7 C6 C5 120.7(3) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C2 121.5(3) . . ?
C6 C7 H7 119.2 . . ?
C2 C7 H7 119.2 . . ?
C9 C8 C5 122.3(3) . . ?
C9 C8 C16 123.4(3) . . ?
C5 C8 C16 114.3(3) . . ?
C8 C9 C10 120.6(3) . . ?
C8 C9 C22 123.4(3) . . ?
C10 C9 C22 115.9(3) . . ?
C11 C10 C15 118.2(3) . . ?
C11 C10 C9 120.3(3) . . ?
C15 C10 C9 121.5(3) . . ?
C12 C11 C10 120.8(3) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C13 C12 C11 120.6(3) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C12 119.3(3) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 120.6(3) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C10 120.4(3) . . ?
C14 C15 H15 119.8 . . ?
C10 C15 H15 119.8 . . ?
C21 C16 C17 118.6(3) . . ?
C21 C16 C8 121.8(3) . . ?
C17 C16 C8 119.6(3) . . ?
C18 C17 C16 120.0(4) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C19 C18 C17 121.4(4) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C18 C19 C20 119.4(4) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C19 C20 C21 120.3(4) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C16 C21 C20 120.3(4) . . ?
C16 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C27 C22 C23 117.6(3) . . ?
C27 C22 C9 121.6(3) . . ?
C23 C22 C9 120.7(3) . . ?
C22 C23 C24 120.1(4) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C25 C24 C23 121.2(4) . . ?
C25 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?
C24 C25 C26 119.9(4) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C25 C26 C27 119.3(4) . . ?
C25 C26 H26 120.4 . . ?
C27 C26 H26 120.4 . . ?
C22 C27 C26 121.9(4) . . ?
C22 C27 H27 119.1 . . ?
C26 C27 H27 119.1 . . ?
C33 C28 N1 133.3(3) . . ?
C33 C28 C29 122.3(3) . . ?
N1 C28 C29 104.4(3) . . ?
N2 C29 C30 131.1(3) . . ?
N2 C29 C28 110.2(3) . . ?
C30 C29 C28 118.6(3) . . ?
C31 C30 C29 119.5(3) . . ?
C31 C30 H30 120.3 . . ?
C29 C30 H30 120.3 . . ?
C30 C31 C32 120.8(3) . . ?
C30 C31 Cl2 118.8(3) . . ?
C32 C31 Cl2 120.4(3) . . ?
C33 C32 C31 120.9(3) . . ?
C33 C32 Cl1 118.6(3) . . ?
C31 C32 Cl1 120.5(3) . . ?
C28 C33 C32 117.9(3) . . ?
C28 C33 H33 121.1 . . ?
C32 C33 H33 121.1 . . ?
H1WA O1W H1WB 109.3 . . ?

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
C29 N2 C1 N1 -0.5(3) . . . . ?
C29 N2 C1 C2 177.3(3) . . . . ?
C28 N1 C1 N2 1.6(4) . . . . ?
C28 N1 C1 C2 -176.2(3) . . . . ?
N2 C1 C2 C7 0.5(5) . . . . ?
N1 C1 C2 C7 178.1(3) . . . . ?
N2 C1 C2 C3 -178.0(3) . . . . ?
N1 C1 C2 C3 -0.4(5) . . . . ?
C7 C2 C3 C4 0.1(5) . . . . ?
C1 C2 C3 C4 178.6(3) . . . . ?
C2 C3 C4 C5 -1.7(5) . . . . ?
C3 C4 C5 C6 1.4(5) . . . . ?
C3 C4 C5 C8 -175.7(3) . . . . ?
C4 C5 C6 C7 0.5(5) . . . . ?
C8 C5 C6 C7 177.5(3) . . . . ?
C5 C6 C7 C2 -2.2(5) . . . . ?
C3 C2 C7 C6 1.8(5) . . . . ?
C1 C2 C7 C6 -176.7(3) . . . . ?
C4 C5 C8 C9 -55.7(5) . . . . ?
C6 C5 C8 C9 127.4(4) . . . . ?
C4 C5 C8 C16 121.4(3) . . . . ?
C6 C5 C8 C16 -55.5(4) . . . . ?
C5 C8 C9 C10 -11.4(5) . . . . ?
C16 C8 C9 C10 171.8(3) . . . . ?
C5 C8 C9 C22 165.4(3) . . . . ?
C16 C8 C9 C22 -11.4(5) . . . . ?
C8 C9 C10 C11 127.4(4) . . . . ?
C22 C9 C10 C11 -49.6(4) . . . . ?
C8 C9 C10 C15 -53.4(5) . . . . ?
C22 C9 C10 C15 129.6(3) . . . . ?
C15 C10 C11 C12 3.1(5) . . . . ?
C9 C10 C11 C12 -177.6(3) . . . . ?
C10 C11 C12 C13 -3.0(6) . . . . ?
C11 C12 C13 C14 1.3(6) . . . . ?
C12 C13 C14 C15 0.1(6) . . . . ?
C13 C14 C15 C10 0.1(5) . . . . ?
C11 C10 C15 C14 -1.7(5) . . . . ?
C9 C10 C15 C14 179.1(3) . . . . ?
C9 C8 C16 C21 -57.1(5) . . . . ?
C5 C8 C16 C21 125.9(3) . . . . ?
C9 C8 C16 C17 126.6(4) . . . . ?
C5 C8 C16 C17 -50.4(4) . . . . ?
C21 C16 C17 C18 2.1(5) . . . . ?
C8 C16 C17 C18 178.5(3) . . . . ?
C16 C17 C18 C19 -1.8(5) . . . . ?
C17 C18 C19 C20 0.5(6) . . . . ?
C18 C19 C20 C21 0.5(5) . . . . ?
C17 C16 C21 C20 -1.1(5) . . . . ?
C8 C16 C21 C20 -177.5(3) . . . . ?
C19 C20 C21 C16 -0.2(5) . . . . ?
C8 C9 C22 C27 135.3(4) . . . . ?
C10 C9 C22 C27 -47.8(5) . . . . ?
C8 C9 C22 C23 -48.3(5) . . . . ?
C10 C9 C22 C23 128.6(3) . . . . ?
C27 C22 C23 C24 -1.2(5) . . . . ?
C9 C22 C23 C24 -177.7(3) . . . . ?
C22 C23 C24 C25 -0.6(7) . . . . ?
C23 C24 C25 C26 1.4(7) . . . . ?
C24 C25 C26 C27 -0.3(7) . . . . ?
C23 C22 C27 C26 2.3(5) . . . . ?
C9 C22 C27 C26 178.8(3) . . . . ?
C25 C26 C27 C22 -1.6(6) . . . . ?
C1 N1 C28 C33 178.3(3) . . . . ?
C1 N1 C28 C29 -2.0(3) . . . . ?
C1 N2 C29 C30 -178.0(3) . . . . ?
C1 N2 C29 C28 -0.8(3) . . . . ?
C33 C28 C29 N2 -178.6(3) . . . . ?
N1 C28 C29 N2 1.7(3) . . . . ?
C33 C28 C29 C30 -0.9(5) . . . . ?
N1 C28 C29 C30 179.3(3) . . . . ?
N2 C29 C30 C31 178.6(3) . . . . ?
C28 C29 C30 C31 1.5(5) . . . . ?
C29 C30 C31 C32 -1.8(5) . . . . ?
C29 C30 C31 Cl2 178.5(2) . . . . ?
C30 C31 C32 C33 1.5(5) . . . . ?
Cl2 C31 C32 C33 -178.8(2) . . . . ?
C30 C31 C32 Cl1 -179.3(2) . . . . ?
Cl2 C31 C32 Cl1 0.4(4) . . . . ?
N1 C28 C33 C32 -179.7(3) . . . . ?
C29 C28 C33 C32 0.6(5) . . . . ?
C31 C32 C33 C28 -0.9(5) . . . . ?
Cl1 C32 C33 C28 180.0(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.047
####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1486489'
_audit_update_record             
;
2016-06-19 deposited with the CCDC.
2016-08-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C35 H28 N2 1.5(CH3OH)'
_chemical_formula_sum            'C36.50 H34 N2 O1.50'
_chemical_formula_weight         524.66

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'

_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                   7.275(2)
_cell_length_b                   9.280(3)
_cell_length_c                   23.640(7)
_cell_angle_alpha                83.829(6)
_cell_angle_beta                 88.466(6)
_cell_angle_gamma                79.361(6)
_cell_volume                     1559.4(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2430
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      26.35

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.117
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             558
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_T_max  0.913
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX II CCD area-detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_reflns_number            8001
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_av_sigmaI/netI    0.1399
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.98
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5429
_reflns_number_gt                1951
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_reduction        SAINT-Plus
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XP (Sheldrick, 1998)'
_computing_publication_material  XP

_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)+(0.0654P)²+0.0000P] 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     SHELXL
_refine_ls_extinction_coef       0.0051(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5429
_refine_ls_number_parameters     374
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.2151
_refine_ls_R_factor_gt           0.0833
_refine_ls_wR_factor_ref         0.2063
_refine_ls_wR_factor_gt          0.1692
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      1.010
_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
N1 N 0.4680(5) 1.0610(4) 0.07615(13) 0.0518(9) Uani 1 1 d . . .
H1 H 0.3592 1.0503 0.0891 0.062 Uiso 1 1 calc R . .
N2 N 0.7775(5) 1.0256(4) 0.06715(14) 0.0537(10) Uani 1 1 d . . .
C1 C 0.6326(6) 0.9832(4) 0.09562(17) 0.0478(11) Uani 1 1 d . . .
C2 C 0.6484(6) 0.8711(5) 0.14406(17) 0.0495(11) Uani 1 1 d . . .
C3 C 0.4938(6) 0.8340(5) 0.17158(17) 0.0580(12) Uani 1 1 d . . .
H3 H 0.3754 0.8813 0.1593 0.070 Uiso 1 1 calc R . .
C4 C 0.5116(6) 0.7258(5) 0.21800(17) 0.0585(12) Uani 1 1 d . . .
H4 H 0.4046 0.7001 0.2356 0.070 Uiso 1 1 calc R . .
C5 C 0.6852(7) 0.6563(5) 0.23813(17) 0.0535(12) Uani 1 1 d . . .
C6 C 0.8398(6) 0.6934(5) 0.20931(17) 0.0583(13) Uani 1 1 d . . .
H6 H 0.9586 0.6467 0.2215 0.070 Uiso 1 1 calc R . .
C7 C 0.8223(6) 0.7978(5) 0.16302(17) 0.0538(12) Uani 1 1 d . . .
H7 H 0.9292 0.8195 0.1441 0.065 Uiso 1 1 calc R . .
C8 C 0.6996(6) 0.5494(5) 0.29044(18) 0.0558(12) Uani 1 1 d . . .
C9 C 0.7924(6) 0.5680(5) 0.33618(19) 0.0583(12) Uani 1 1 d . . .
C10 C 0.8843(7) 0.6984(5) 0.33775(17) 0.0593(12) Uani 1 1 d . . .
C11 C 1.0726(8) 0.6742(6) 0.34868(19) 0.0727(14) Uani 1 1 d . . .
H11 H 1.1379 0.5781 0.3556 0.087 Uiso 1 1 calc R . .
C12 C 1.1671(9) 0.7913(9) 0.3495(2) 0.0923(18) Uani 1 1 d . . .
H12 H 1.2947 0.7740 0.3568 0.111 Uiso 1 1 calc R . .
C13 C 1.0683(12) 0.9341(8) 0.3392(3) 0.104(2) Uani 1 1 d . . .
H13 H 1.1290 1.0140 0.3388 0.125 Uiso 1 1 calc R . .
C14 C 0.8797(11) 0.9556(7) 0.3296(3) 0.104(2) Uani 1 1 d . . .
H14 H 0.8121 1.0513 0.3238 0.125 Uiso 1 1 calc R . .
C15 C 0.7905(8) 0.8418(6) 0.3284(2) 0.0786(15) Uani 1 1 d . . .
H15 H 0.6629 0.8601 0.3210 0.094 Uiso 1 1 calc R . .
C16 C 0.8189(6) 0.4613(5) 0.38861(19) 0.0594(13) Uani 1 1 d . . .
C17 C 0.7684(8) 0.5122(6) 0.4408(2) 0.0917(18) Uani 1 1 d . . .
H17 H 0.7132 0.6103 0.4426 0.110 Uiso 1 1 calc R . .
C18 C 0.8000(9) 0.4172(8) 0.4902(2) 0.107(2) Uani 1 1 d . . .
H18 H 0.7660 0.4521 0.5251 0.129 Uiso 1 1 calc R . .
C19 C 0.8799(9) 0.2737(8) 0.4883(3) 0.099(2) Uani 1 1 d . . .
H19 H 0.9028 0.2105 0.5217 0.119 Uiso 1 1 calc R . .
C20 C 0.9261(8) 0.2235(6) 0.4366(3) 0.0892(17) Uani 1 1 d . . .
H20 H 0.9773 0.1245 0.4349 0.107 Uiso 1 1 calc R . .
C21 C 0.8987(6) 0.3159(6) 0.38745(19) 0.0703(14) Uani 1 1 d . . .
H21 H 0.9344 0.2798 0.3528 0.084 Uiso 1 1 calc R . .
C22 C 0.6004(6) 0.4233(5) 0.2861(2) 0.0578(12) Uani 1 1 d . . .
C23 C 0.4829(7) 0.3748(6) 0.3288(2) 0.0765(15) Uani 1 1 d . . .
H23 H 0.4656 0.4205 0.3622 0.092 Uiso 1 1 calc R . .
C24 C 0.3918(8) 0.2597(7) 0.3219(3) 0.0947(19) Uani 1 1 d . . .
H24 H 0.3129 0.2295 0.3506 0.114 Uiso 1 1 calc R . .
C25 C 0.4163(9) 0.1901(7) 0.2737(3) 0.105(2) Uani 1 1 d . . .
H25 H 0.3567 0.1111 0.2700 0.126 Uiso 1 1 calc R . .
C26 C 0.5280(9) 0.2361(7) 0.2309(3) 0.1001(19) Uani 1 1 d . . .
H26 H 0.5432 0.1898 0.1977 0.120 Uiso 1 1 calc R . .
C27 C 0.6195(7) 0.3528(6) 0.2373(2) 0.0791(15) Uani 1 1 d . . .
H27 H 0.6951 0.3838 0.2078 0.095 Uiso 1 1 calc R . .
C28 C 0.6976(6) 1.1366(5) 0.02612(17) 0.0484(11) Uani 1 1 d . . .
C29 C 0.5049(6) 1.1607(4) 0.03181(16) 0.0457(11) Uani 1 1 d . . .
C30 C 0.3901(6) 1.2680(5) -0.00260(17) 0.0565(12) Uani 1 1 d . . .
H30 H 0.2607 1.2818 0.0014 0.068 Uiso 1 1 calc R . .
C31 C 0.4731(7) 1.3539(5) -0.04300(17) 0.0561(12) Uani 1 1 d . . .
C32 C 0.6699(7) 1.3319(5) -0.04945(17) 0.0562(12) Uani 1 1 d . . .
C33 C 0.7820(6) 1.2225(5) -0.01551(17) 0.0571(12) Uani 1 1 d . . .
H33 H 0.9112 1.2059 -0.0201 0.069 Uiso 1 1 calc R . .
C34 C 0.7592(7) 1.4290(5) -0.09363(18) 0.0794(16) Uani 1 1 d . . .
H34A H 0.8928 1.4009 -0.0917 0.119 Uiso 1 1 calc R . .
H34B H 0.7231 1.5302 -0.0863 0.119 Uiso 1 1 calc R . .
H34C H 0.7181 1.4174 -0.1309 0.119 Uiso 1 1 calc R . .
C35 C 0.3500(7) 1.4751(5) -0.08025(18) 0.0730(14) Uani 1 1 d . . .
H35A H 0.2215 1.4784 -0.0692 0.110 Uiso 1 1 calc R . .
H35B H 0.3658 1.4555 -0.1193 0.110 Uiso 1 1 calc R . .
H35C H 0.3848 1.5681 -0.0759 0.110 Uiso 1 1 calc R . .
O1 O 0.1050(4) 0.0650(4) 0.11253(14) 0.0784(10) Uani 1 1 d . . .
H1A H 0.0192 0.0485 0.0938 0.118 Uiso 1 1 d R . .
C36 C 0.0354(9) 0.1660(8) 0.1507(3) 0.131(2) Uani 1 1 d U . .
H36A H -0.0213 0.1171 0.1825 0.197 Uiso 1 1 calc R . .
H36B H -0.0564 0.2431 0.1321 0.197 Uiso 1 1 calc R . .
H36C H 0.1358 0.2077 0.1638 0.197 Uiso 1 1 calc R . .
O2 O 0.5889(15) 0.9162(16) 0.5282(6) 0.224(6) Uani 0.50 1 d PU . .
C37 C 0.5173(19) 0.9399(16) 0.4628(5) 0.126(5) Uani 0.50 1 d PU . .
H37A H 0.6173 0.9432 0.4349 0.152 Uiso 1 1 calc R . .
H37B H 0.4402 0.8702 0.4542 0.152 Uiso 1 1 calc R . .


_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
N1 C1 1.344(4) . ?
N1 C29 1.377(5) . ?
N1 H1 0.8600 . ?
N2 C1 1.332(5) . ?
N2 C28 1.391(5) . ?
C1 C2 1.454(5) . ?
C2 C3 1.365(5) . ?
C2 C7 1.383(5) . ?
C3 C4 1.398(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.378(5) . ?
C5 C8 1.494(5) . ?
C6 C7 1.373(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.333(5) . ?
C8 C22 1.497(6) . ?
C9 C16 1.494(6) . ?
C9 C10 1.491(6) . ?
C10 C11 1.373(6) . ?
C10 C15 1.377(6) . ?
C11 C12 1.391(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.386(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.371(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.341(7) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C21 1.370(6) . ?
C16 C17 1.384(6) . ?
C17 C18 1.382(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.356(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.365(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.365(6) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C27 1.380(6) . ?
C22 C23 1.395(6) . ?
C23 C24 1.382(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.360(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.363(7) . ?
C25 H25 0.9300 . ?
C26 C27 1.394(7) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 C29 1.384(5) . ?
C28 C33 1.400(5) . ?
C29 C30 1.380(5) . ?
C30 C31 1.377(5) . ?
C30 H30 0.9300 . ?
C31 C32 1.415(6) . ?
C31 C35 1.516(5) . ?
C32 C33 1.376(5) . ?
C32 C34 1.517(5) . ?
C33 H33 0.9300 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
O1 C36 1.390(6) . ?
O1 H1A 0.8200 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
O2 C37 1.448(14) 2_676 ?
O2 C37 1.626(13) . ?
C37 O2 1.448(14) 2_676 ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C29 107.7(3) . . ?
C1 N1 H1 126.1 . . ?
C29 N1 H1 126.1 . . ?
C1 N2 C28 104.7(3) . . ?
N2 C1 N1 112.3(3) . . ?
N2 C1 C2 124.5(4) . . ?
N1 C1 C2 123.1(4) . . ?
C3 C2 C7 118.2(4) . . ?
C3 C2 C1 121.4(4) . . ?
C7 C2 C1 120.3(4) . . ?
C2 C3 C4 120.6(4) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 121.1(4) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 117.5(4) . . ?
C4 C5 C8 119.8(4) . . ?
C6 C5 C8 122.7(4) . . ?
C7 C6 C5 121.4(4) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C2 121.1(4) . . ?
C6 C7 H7 119.5 . . ?
C2 C7 H7 119.5 . . ?
C9 C8 C5 121.8(4) . . ?
C9 C8 C22 124.4(4) . . ?
C5 C8 C22 113.8(4) . . ?
C8 C9 C16 124.2(4) . . ?
C8 C9 C10 121.3(4) . . ?
C16 C9 C10 114.5(4) . . ?
C11 C10 C15 118.3(5) . . ?
C11 C10 C9 118.3(5) . . ?
C15 C10 C9 123.4(5) . . ?
C10 C11 C12 121.0(5) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C13 C12 C11 119.0(6) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C14 C13 C12 119.0(6) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C15 C14 C13 121.4(6) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C14 C15 C10 121.2(6) . . ?
C14 C15 H15 119.4 . . ?
C10 C15 H15 119.4 . . ?
C21 C16 C17 118.4(4) . . ?
C21 C16 C9 122.6(4) . . ?
C17 C16 C9 119.0(5) . . ?
C18 C17 C16 120.0(5) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C19 C18 C17 120.8(6) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C20 118.9(5) . . ?
C18 C19 H19 120.6 . . ?
C20 C19 H19 120.6 . . ?
C19 C20 C21 121.2(5) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C20 C21 C16 120.6(5) . . ?
C20 C21 H21 119.7 . . ?
C16 C21 H21 119.7 . . ?
C27 C22 C23 117.3(5) . . ?
C27 C22 C8 119.4(4) . . ?
C23 C22 C8 123.3(5) . . ?
C24 C23 C22 120.7(5) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C25 C24 C23 120.8(6) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C26 C25 C24 120.0(6) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 C27 119.7(6) . . ?
C25 C26 H26 120.2 . . ?
C27 C26 H26 120.2 . . ?
C26 C27 C22 121.6(5) . . ?
C26 C27 H27 119.2 . . ?
C22 C27 H27 119.2 . . ?
C29 C28 N2 109.7(4) . . ?
C29 C28 C33 120.0(4) . . ?
N2 C28 C33 130.3(4) . . ?
N1 C29 C30 132.4(4) . . ?
N1 C29 C28 105.5(3) . . ?
C30 C29 C28 122.1(4) . . ?
C31 C30 C29 118.0(4) . . ?
C31 C30 H30 121.0 . . ?
C29 C30 H30 121.0 . . ?
C30 C31 C32 121.0(4) . . ?
C30 C31 C35 118.9(4) . . ?
C32 C31 C35 120.1(4) . . ?
C33 C32 C31 120.2(4) . . ?
C33 C32 C34 119.4(4) . . ?
C31 C32 C34 120.3(4) . . ?
C32 C33 C28 118.7(4) . . ?
C32 C33 H33 120.6 . . ?
C28 C33 H33 120.6 . . ?
C32 C34 H34A 109.5 . . ?
C32 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C32 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C31 C35 H35A 109.5 . . ?
C31 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C31 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C36 O1 H1A 109.9 . . ?
O1 C36 H36A 109.5 . . ?
O1 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
O1 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C37 O2 C37 89.6(8) 2_676 . ?
O2 C37 O2 90.4(8) 2_676 . ?
O2 C37 H37A 113.6 2_676 . ?
O2 C37 H37A 113.6 . . ?
O2 C37 H37B 113.6 2_676 . ?
O2 C37 H37B 113.6 . . ?
H37A C37 H37B 110.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C28 N2 C1 N1 -1.0(4) . . . . ?
C28 N2 C1 C2 -178.2(4) . . . . ?
C29 N1 C1 N2 0.3(5) . . . . ?
C29 N1 C1 C2 177.5(4) . . . . ?
N2 C1 C2 C3 179.4(4) . . . . ?
N1 C1 C2 C3 2.6(6) . . . . ?
N2 C1 C2 C7 -1.3(6) . . . . ?
N1 C1 C2 C7 -178.2(4) . . . . ?
C7 C2 C3 C4 0.6(6) . . . . ?
C1 C2 C3 C4 179.9(4) . . . . ?
C2 C3 C4 C5 1.7(6) . . . . ?
C3 C4 C5 C6 -2.6(6) . . . . ?
C3 C4 C5 C8 175.4(4) . . . . ?
C4 C5 C6 C7 1.4(6) . . . . ?
C8 C5 C6 C7 -176.6(4) . . . . ?
C5 C6 C7 C2 0.9(7) . . . . ?
C3 C2 C7 C6 -1.8(6) . . . . ?
C1 C2 C7 C6 178.9(4) . . . . ?
C4 C5 C8 C9 -121.7(5) . . . . ?
C6 C5 C8 C9 56.2(6) . . . . ?
C4 C5 C8 C22 57.9(5) . . . . ?
C6 C5 C8 C22 -124.2(5) . . . . ?
C5 C8 C9 C16 -177.1(4) . . . . ?
C22 C8 C9 C16 3.4(7) . . . . ?
C5 C8 C9 C10 1.0(7) . . . . ?
C22 C8 C9 C10 -178.6(4) . . . . ?
C8 C9 C10 C11 -123.1(5) . . . . ?
C16 C9 C10 C11 55.1(6) . . . . ?
C8 C9 C10 C15 56.3(7) . . . . ?
C16 C9 C10 C15 -125.4(5) . . . . ?
C15 C10 C11 C12 -0.9(7) . . . . ?
C9 C10 C11 C12 178.6(4) . . . . ?
C10 C11 C12 C13 0.1(8) . . . . ?
C11 C12 C13 C14 1.2(9) . . . . ?
C12 C13 C14 C15 -1.9(10) . . . . ?
C13 C14 C15 C10 1.2(9) . . . . ?
C11 C10 C15 C14 0.2(8) . . . . ?
C9 C10 C15 C14 -179.2(5) . . . . ?
C8 C9 C16 C21 55.9(7) . . . . ?
C10 C9 C16 C21 -122.3(5) . . . . ?
C8 C9 C16 C17 -126.9(5) . . . . ?
C10 C9 C16 C17 54.9(6) . . . . ?
C21 C16 C17 C18 0.5(8) . . . . ?
C9 C16 C17 C18 -176.9(5) . . . . ?
C16 C17 C18 C19 -0.2(9) . . . . ?
C17 C18 C19 C20 -1.1(10) . . . . ?
C18 C19 C20 C21 2.0(9) . . . . ?
C19 C20 C21 C16 -1.8(8) . . . . ?
C17 C16 C21 C20 0.5(7) . . . . ?
C9 C16 C21 C20 177.7(5) . . . . ?
C9 C8 C22 C27 -135.9(5) . . . . ?
C5 C8 C22 C27 44.5(6) . . . . ?
C9 C8 C22 C23 46.1(6) . . . . ?
C5 C8 C22 C23 -133.5(4) . . . . ?
C27 C22 C23 C24 0.6(7) . . . . ?
C8 C22 C23 C24 178.6(5) . . . . ?
C22 C23 C24 C25 0.7(8) . . . . ?
C23 C24 C25 C26 -1.6(9) . . . . ?
C24 C25 C26 C27 1.2(9) . . . . ?
C25 C26 C27 C22 0.2(8) . . . . ?
C23 C22 C27 C26 -1.1(7) . . . . ?
C8 C22 C27 C26 -179.2(4) . . . . ?
C1 N2 C28 C29 1.3(4) . . . . ?
C1 N2 C28 C33 179.3(4) . . . . ?
C1 N1 C29 C30 -178.8(4) . . . . ?
C1 N1 C29 C28 0.5(4) . . . . ?
N2 C28 C29 N1 -1.1(4) . . . . ?
C33 C28 C29 N1 -179.3(4) . . . . ?
N2 C28 C29 C30 178.3(4) . . . . ?
C33 C28 C29 C30 0.1(6) . . . . ?
N1 C29 C30 C31 178.2(4) . . . . ?
C28 C29 C30 C31 -1.0(6) . . . . ?
C29 C30 C31 C32 0.7(6) . . . . ?
C29 C30 C31 C35 -178.4(4) . . . . ?
C30 C31 C32 C33 0.6(6) . . . . ?
C35 C31 C32 C33 179.7(4) . . . . ?
C30 C31 C32 C34 -179.2(4) . . . . ?
C35 C31 C32 C34 -0.1(6) . . . . ?
C31 C32 C33 C28 -1.6(6) . . . . ?
C34 C32 C33 C28 178.2(4) . . . . ?
C29 C28 C33 C32 1.2(6) . . . . ?
N2 C28 C33 C32 -176.6(4) . . . . ?
C37 O2 C37 O2 0.000(1) 2_676 . . 2_676 ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.053
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
