# Electronic Supplementary Material (ESI) for ChemComm.
# 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_140611_zxr_505_059_cu
_database_code_depnum_ccdc_archive 'CCDC 1405389'
_audit_update_record             
;
2015-06-06 deposited with the CCDC.
2016-08-02 downloaded from the CCDC.
;
_audit_creation_date             2014-06-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C28 H23 Br N2 O2'
_chemical_formula_sum            'C28 H23 Br N2 O2'
_chemical_formula_weight         499.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2 o8 Br1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   8.1067(3)
_cell_length_b                   15.9970(7)
_cell_length_c                   18.8373(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.636(4)
_cell_angle_gamma                90.00
_cell_volume                     2408.41(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4987
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.2771
_cell_measurement_theta_min      3.6437
_exptl_absorpt_coefficient_mu    2.539
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36120
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8040
_diffrn_reflns_theta_full        67.39
_diffrn_reflns_theta_max         67.39
_diffrn_reflns_theta_min         3.65
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0292614000
_diffrn_orient_matrix_UB_12      -0.0386645000
_diffrn_orient_matrix_UB_13      0.0759493000
_diffrn_orient_matrix_UB_21      0.0497242000
_diffrn_orient_matrix_UB_22      -0.0834139000
_diffrn_orient_matrix_UB_23      -0.0314773000
_diffrn_orient_matrix_UB_31      0.1838823000
_diffrn_orient_matrix_UB_32      0.0287533000
_diffrn_orient_matrix_UB_33      0.0109341000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3857
_reflns_number_total             4169
_reflns_odcompleteness_completeness 98.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         2.609
_refine_diff_density_min         -0.859
_refine_diff_density_rms         0.176
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.839
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1332
_refine_ls_R_factor_gt           0.1289
_refine_ls_restrained_S_all      1.839
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3940
_refine_ls_wR_factor_ref         0.3992
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C16(H16)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C14(H14),
 C15(H15), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C24(H24), C25(H25),
  C26(H26), C27(H27), C28(H28)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Br1 Br 1.13128(10) 0.02102(5) -0.12736(4) 0.0664(5) Uani 1 d . . .
O1 O 0.7308(9) 0.3251(5) 0.1758(4) 0.094(2) Uani 1 d . . .
O2 O 0.6599(8) 0.3847(3) 0.0325(4) 0.0754(16) Uani 1 d . . .
N1 N 0.5546(8) 0.2295(4) -0.0606(3) 0.0599(15) Uani 1 d . . .
H1 H 0.4885 0.2473 -0.0981 0.072 Uiso 1 calc . . R
N2 N 0.6352(8) 0.3039(3) 0.0543(3) 0.0561(14) Uani 1 d . . .
C1 C 0.5878(8) 0.1989(4) 0.1270(3) 0.0515(15) Uani 1 d . . .
C2 C 0.5860(11) 0.1437(6) 0.1842(4) 0.071(2) Uani 1 d . . .
H2 H 0.6384 0.1584 0.2302 0.085 Uiso 1 calc . . R
C3 C 0.5073(14) 0.0680(7) 0.1726(6) 0.088(3) Uani 1 d . . .
H3 H 0.5024 0.0318 0.2108 0.105 Uiso 1 calc . . R
C4 C 0.4365(11) 0.0466(6) 0.1045(7) 0.083(3) Uani 1 d . . .
H4 H 0.3861 -0.0056 0.0968 0.099 Uiso 1 calc . . R
C5 C 0.4361(10) 0.0988(5) 0.0466(4) 0.0652(19) Uani 1 d . . .
H5 H 0.3883 0.0821 0.0004 0.078 Uiso 1 calc . . R
C6 C 0.5101(8) 0.1782(5) 0.0590(4) 0.0499(14) Uani 1 d . . .
C7 C 0.5111(8) 0.2515(4) 0.0081(3) 0.0504(14) Uani 1 d . . .
C8 C 0.6588(9) 0.2818(5) 0.1266(4) 0.0574(16) Uani 1 d . . .
C9 C 0.8286(14) 0.3921(6) 0.0197(8) 0.100(4) Uani 1 d . . .
H9A H 0.8382 0.3658 -0.0253 0.150 Uiso 1 calc . . GR
H9B H 0.9030 0.3653 0.0579 0.150 Uiso 1 calc . . GR
H9C H 0.8577 0.4501 0.0177 0.150 Uiso 1 calc . . GR
C10 C 0.6884(9) 0.1837(4) -0.0730(3) 0.0501(14) Uani 1 d . . .
C11 C 0.8172(8) 0.1545(4) -0.0180(3) 0.0461(13) Uani 1 d . . .
H11 H 0.8153 0.1683 0.0298 0.055 Uiso 1 calc . . R
C12 C 0.9438(8) 0.1062(4) -0.0352(3) 0.0478(13) Uani 1 d . . .
H12 H 1.0244 0.0846 0.0011 0.057 Uiso 1 calc . . R
C13 C 0.9522(8) 0.0895(4) -0.1059(3) 0.0455(13) Uani 1 d . . .
C14 C 0.8351(9) 0.1206(4) -0.1614(3) 0.0513(14) Uani 1 d . . .
H14 H 0.8431 0.1093 -0.2091 0.062 Uiso 1 calc . . R
C15 C 0.7059(9) 0.1688(4) -0.1442(3) 0.0526(15) Uani 1 d . . .
H15 H 0.6288 0.1919 -0.1811 0.063 Uiso 1 calc . . R
C16 C 0.3222(8) 0.2826(4) -0.0057(3) 0.0521(14) Uani 1 d . . .
H16 H 0.2534 0.2320 -0.0127 0.062 Uiso 1 calc . . R
C17 C 0.2801(9) 0.3250(6) 0.0630(4) 0.0639(18) Uani 1 d . . .
C18 C 0.3114(12) 0.4065(7) 0.0802(6) 0.086(3) Uani 1 d . . .
H18 H 0.3599 0.4419 0.0504 0.103 Uiso 1 calc . . R
C19 C 0.267(2) 0.4353(13) 0.1457(11) 0.140(7) Uani 1 d . . .
H19 H 0.2850 0.4913 0.1580 0.168 Uiso 1 calc . . R
C20 C 0.202(3) 0.387(2) 0.1892(8) 0.182(13) Uani 1 d . . .
H20 H 0.1798 0.4079 0.2327 0.218 Uiso 1 calc . . R
C21 C 0.167(2) 0.3066(18) 0.1706(11) 0.152(8) Uani 1 d . . .
H21 H 0.1178 0.2727 0.2012 0.183 Uiso 1 calc . . R
C22 C 0.2034(14) 0.2733(8) 0.1070(6) 0.093(3) Uani 1 d . . .
H22 H 0.1771 0.2182 0.0942 0.111 Uiso 1 calc . . R
C23 C 0.2683(8) 0.3362(4) -0.0731(3) 0.0475(13) Uani 1 d . . .
C24 C 0.3458(14) 0.4061(5) -0.0940(5) 0.074(2) Uani 1 d . . .
H24 H 0.4446 0.4243 -0.0658 0.088 Uiso 1 calc . . R
C25 C 0.2823(19) 0.4502(7) -0.1550(6) 0.099(3) Uani 1 d . . .
H25 H 0.3379 0.4972 -0.1680 0.119 Uiso 1 calc . . R
C26 C 0.1398(16) 0.4248(7) -0.1956(7) 0.097(3) Uani 1 d . . .
H26 H 0.0944 0.4568 -0.2353 0.117 Uiso 1 calc . . R
C27 C 0.0616(14) 0.3566(9) -0.1816(7) 0.104(4) Uani 1 d . . .
H27 H -0.0324 0.3386 -0.2131 0.124 Uiso 1 calc . . R
C28 C 0.1219(12) 0.3093(7) -0.1167(5) 0.079(2) Uani 1 d . . .
H28 H 0.0646 0.2624 -0.1046 0.094 Uiso 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
Br1 C13 1.916(6) . ?
O1 C8 1.225(9) . ?
O2 N2 1.380(8) . ?
O2 C9 1.433(12) . ?
N1 H1 0.8600 . ?
N1 C7 1.441(8) . ?
N1 C10 1.361(9) . ?
N2 C7 1.476(9) . ?
N2 C8 1.389(9) . ?
C1 C2 1.394(11) . ?
C1 C6 1.369(9) . ?
C1 C8 1.447(11) . ?
C2 H2 0.9300 . ?
C2 C3 1.369(16) . ?
C3 H3 0.9300 . ?
C3 C4 1.359(16) . ?
C4 H4 0.9300 . ?
C4 C5 1.374(13) . ?
C5 H5 0.9300 . ?
C5 C6 1.407(11) . ?
C6 C7 1.516(10) . ?
C7 C16 1.589(8) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.422(8) . ?
C10 C15 1.392(9) . ?
C11 H11 0.9300 . ?
C11 C12 1.366(9) . ?
C12 H12 0.9300 . ?
C12 C13 1.371(9) . ?
C13 C14 1.382(9) . ?
C14 H14 0.9300 . ?
C14 C15 1.382(10) . ?
C15 H15 0.9300 . ?
C16 H16 0.9800 . ?
C16 C17 1.548(9) . ?
C16 C23 1.533(9) . ?
C17 C18 1.357(14) . ?
C17 C22 1.389(14) . ?
C18 H18 0.9300 . ?
C18 C19 1.419(19) . ?
C19 H19 0.9300 . ?
C19 C20 1.30(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.35(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.39(2) . ?
C22 H22 0.9300 . ?
C23 C24 1.372(11) . ?
C23 C28 1.393(11) . ?
C24 H24 0.9300 . ?
C24 C25 1.373(14) . ?
C25 H25 0.9300 . ?
C25 C26 1.338(18) . ?
C26 H26 0.9300 . ?
C26 C27 1.311(18) . ?
C27 H27 0.9300 . ?
C27 C28 1.450(16) . ?
C28 H28 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 O2 C9 108.5(6) . . ?
C7 N1 H1 116.3 . . ?
C10 N1 H1 116.3 . . ?
C10 N1 C7 127.4(5) . . ?
O2 N2 C7 118.4(6) . . ?
O2 N2 C8 121.7(6) . . ?
C8 N2 C7 113.7(6) . . ?
C2 C1 C8 129.8(7) . . ?
C6 C1 C2 120.5(7) . . ?
C6 C1 C8 109.7(6) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.1(8) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 119.0(8) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 H4 118.6 . . ?
C3 C4 C5 122.8(10) . . ?
C5 C4 H4 118.6 . . ?
C4 C5 H5 120.9 . . ?
C4 C5 C6 118.1(8) . . ?
C6 C5 H5 120.9 . . ?
C1 C6 C5 119.4(7) . . ?
C1 C6 C7 110.8(6) . . ?
C5 C6 C7 129.8(6) . . ?
N1 C7 N2 115.0(6) . . ?
N1 C7 C6 114.0(5) . . ?
N1 C7 C16 107.6(5) . . ?
N2 C7 C6 98.2(5) . . ?
N2 C7 C16 117.5(5) . . ?
C6 C7 C16 103.8(5) . . ?
O1 C8 N2 124.7(8) . . ?
O1 C8 C1 130.8(8) . . ?
N2 C8 C1 104.4(6) . . ?
O2 C9 H9A 109.5 . . ?
O2 C9 H9B 109.5 . . ?
O2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 C11 124.1(6) . . ?
N1 C10 C15 118.0(6) . . ?
C15 C10 C11 117.8(6) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.1(6) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.1(5) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 Br1 118.7(4) . . ?
C12 C13 C14 121.7(5) . . ?
C14 C13 Br1 119.6(5) . . ?
C13 C14 H14 120.8 . . ?
C13 C14 C15 118.4(5) . . ?
C15 C14 H14 120.8 . . ?
C10 C15 H15 119.2 . . ?
C14 C15 C10 121.6(6) . . ?
C14 C15 H15 119.2 . . ?
C7 C16 H16 105.9 . . ?
C17 C16 C7 109.9(5) . . ?
C17 C16 H16 105.9 . . ?
C23 C16 C7 116.4(6) . . ?
C23 C16 H16 105.9 . . ?
C23 C16 C17 112.0(5) . . ?
C18 C17 C16 124.2(8) . . ?
C18 C17 C22 120.8(9) . . ?
C22 C17 C16 115.0(8) . . ?
C17 C18 H18 121.4 . . ?
C17 C18 C19 117.1(14) . . ?
C19 C18 H18 121.4 . . ?
C18 C19 H19 118.5 . . ?
C20 C19 C18 123.0(19) . . ?
C20 C19 H19 118.5 . . ?
C19 C20 H20 120.3 . . ?
C19 C20 C21 119.4(14) . . ?
C21 C20 H20 120.3 . . ?
C20 C21 H21 119.2 . . ?
C20 C21 C22 121.6(17) . . ?
C22 C21 H21 119.2 . . ?
C17 C22 H22 121.0 . . ?
C21 C22 C17 118.0(14) . . ?
C21 C22 H22 121.0 . . ?
C24 C23 C16 127.7(7) . . ?
C24 C23 C28 117.9(7) . . ?
C28 C23 C16 114.3(6) . . ?
C23 C24 H24 118.9 . . ?
C23 C24 C25 122.2(9) . . ?
C25 C24 H24 118.9 . . ?
C24 C25 H25 120.3 . . ?
C26 C25 C24 119.3(11) . . ?
C26 C25 H25 120.3 . . ?
C25 C26 H26 118.7 . . ?
C27 C26 C25 122.6(10) . . ?
C27 C26 H26 118.7 . . ?
C26 C27 H27 120.1 . . ?
C26 C27 C28 119.8(10) . . ?
C28 C27 H27 120.1 . . ?
C23 C28 C27 118.0(9) . . ?
C23 C28 H28 121.0 . . ?
C27 C28 H28 121.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C13 C14 C15 179.1(5) . . . . ?
O2 N2 C7 N1 67.3(7) . . . . ?
O2 N2 C7 C6 -171.3(6) . . . . ?
O2 N2 C7 C16 -61.0(8) . . . . ?
O2 N2 C8 O1 -14.0(11) . . . . ?
O2 N2 C8 C1 168.4(6) . . . . ?
N1 C7 C16 C17 -167.8(6) . . . . ?
N1 C7 C16 C23 -39.1(8) . . . . ?
N1 C10 C11 C12 177.6(7) . . . . ?
N1 C10 C15 C14 -177.8(7) . . . . ?
N2 C7 C16 C17 -36.0(8) . . . . ?
N2 C7 C16 C23 92.7(7) . . . . ?
C1 C2 C3 C4 2.2(13) . . . . ?
C1 C6 C7 N1 135.7(6) . . . . ?
C1 C6 C7 N2 13.5(6) . . . . ?
C1 C6 C7 C16 -107.5(6) . . . . ?
C2 C1 C6 C5 -3.5(10) . . . . ?
C2 C1 C6 C7 173.3(6) . . . . ?
C2 C1 C8 O1 -2.1(14) . . . . ?
C2 C1 C8 N2 175.3(7) . . . . ?
C2 C3 C4 C5 -1.9(14) . . . . ?
C3 C4 C5 C6 -1.1(12) . . . . ?
C4 C5 C6 C1 3.8(10) . . . . ?
C4 C5 C6 C7 -172.3(7) . . . . ?
C5 C6 C7 N1 -48.0(9) . . . . ?
C5 C6 C7 N2 -170.1(7) . . . . ?
C5 C6 C7 C16 68.8(8) . . . . ?
C6 C1 C2 C3 0.5(12) . . . . ?
C6 C1 C8 O1 176.1(8) . . . . ?
C6 C1 C8 N2 -6.6(8) . . . . ?
C6 C7 C16 C17 71.0(7) . . . . ?
C6 C7 C16 C23 -160.3(5) . . . . ?
C7 N1 C10 C11 -5.0(12) . . . . ?
C7 N1 C10 C15 179.3(7) . . . . ?
C7 N2 C8 O1 -165.9(7) . . . . ?
C7 N2 C8 C1 16.5(7) . . . . ?
C7 C16 C17 C18 85.1(9) . . . . ?
C7 C16 C17 C22 -95.9(8) . . . . ?
C7 C16 C23 C24 -51.2(10) . . . . ?
C7 C16 C23 C28 129.5(8) . . . . ?
C8 N2 C7 N1 -139.9(6) . . . . ?
C8 N2 C7 C6 -18.5(7) . . . . ?
C8 N2 C7 C16 91.8(7) . . . . ?
C8 C1 C2 C3 178.5(8) . . . . ?
C8 C1 C6 C5 178.2(6) . . . . ?
C8 C1 C6 C7 -5.1(8) . . . . ?
C9 O2 N2 C7 -116.5(9) . . . . ?
C9 O2 N2 C8 92.9(10) . . . . ?
C10 N1 C7 N2 62.4(10) . . . . ?
C10 N1 C7 C6 -50.0(10) . . . . ?
C10 N1 C7 C16 -164.6(7) . . . . ?
C10 C11 C12 C13 3.6(10) . . . . ?
C11 C10 C15 C14 6.1(10) . . . . ?
C11 C12 C13 Br1 -179.7(5) . . . . ?
C11 C12 C13 C14 0.2(10) . . . . ?
C12 C13 C14 C15 -0.8(10) . . . . ?
C13 C14 C15 C10 -2.5(11) . . . . ?
C15 C10 C11 C12 -6.6(10) . . . . ?
C16 C17 C18 C19 -179.3(9) . . . . ?
C16 C17 C22 C21 177.9(11) . . . . ?
C16 C23 C24 C25 -178.3(9) . . . . ?
C16 C23 C28 C27 179.8(9) . . . . ?
C17 C16 C23 C24 76.5(9) . . . . ?
C17 C16 C23 C28 -102.9(8) . . . . ?
C17 C18 C19 C20 1(2) . . . . ?
C18 C17 C22 C21 -3.0(16) . . . . ?
C18 C19 C20 C21 -3(3) . . . . ?
C19 C20 C21 C22 2(3) . . . . ?
C20 C21 C22 C17 1(2) . . . . ?
C22 C17 C18 C19 1.8(15) . . . . ?
C23 C16 C17 C18 -45.9(10) . . . . ?
C23 C16 C17 C22 133.1(8) . . . . ?
C23 C24 C25 C26 0.4(19) . . . . ?
C24 C23 C28 C27 0.4(14) . . . . ?
C24 C25 C26 C27 -4(2) . . . . ?
C25 C26 C27 C28 5(2) . . . . ?
C26 C27 C28 C23 -3.4(19) . . . . ?
C28 C23 C24 C25 1.0(14) . . . . ?

####################################################################### 
# 
# 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_141201_zxr505_1032
_database_code_depnum_ccdc_archive 'CCDC 1405393'
_audit_update_record             
;
2015-06-06 deposited with the CCDC.
2016-08-02 downloaded from the CCDC.
;
_audit_creation_date             2014-12-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C32 H23 N O'
_chemical_formula_sum            'C32 H23 N O'
_chemical_formula_weight         437.51
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 o10 n2'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.2048(6)
_cell_length_b                   9.7962(4)
_cell_length_c                   36.300(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.681(5)
_cell_angle_gamma                90.00
_cell_volume                     4695.3(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3956
_cell_measurement_temperature    170.2
_cell_measurement_theta_max      29.3695
_cell_measurement_theta_min      3.0538
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77352
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.28
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            18409
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.06
_diffrn_ambient_temperature      170.2
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0245799000
_diffrn_orient_matrix_UB_12      -0.0014995000
_diffrn_orient_matrix_UB_13      -0.0172353000
_diffrn_orient_matrix_UB_21      -0.0020955000
_diffrn_orient_matrix_UB_22      -0.0723971000
_diffrn_orient_matrix_UB_23      0.0000746000
_diffrn_orient_matrix_UB_31      -0.0477373000
_diffrn_orient_matrix_UB_32      0.0023297000
_diffrn_orient_matrix_UB_33      -0.0091723000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                6182
_reflns_number_total             8511
_reflns_odcompleteness_completeness 98.35
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     615
_refine_ls_number_reflns         8511
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0473P)²+0.4848P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1186
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C14(H14), C15(H15),
 C17(H17), C18(H18), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C28(H28),
  C29(H29), C30(H30), C31(H31), C32(H32), C33(H33), C34(H34), C35(H35),
 C36(H36), C41(H41), C42(H42), C46(H46), C47(H47), C49(H49), C50(H50), C54(H54),
  C55(H55), C56(H56), C57(H57), C58(H58), C60(H60), C61(H61), C62(H62),
 C63(H63), C64(H64)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C51(H51A,H51B,H51C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.13363(9) 0.73338(12) 0.06881(3) 0.0414(3) Uani 1 d . . .
N1 N 0.29488(10) 0.79465(14) 0.08879(4) 0.0313(3) Uani 1 d . . .
C1 C -0.02506(13) 0.83738(18) 0.12552(5) 0.0387(4) Uani 1 d . . .
H1 H -0.0247 0.7839 0.1037 0.046 Uiso 1 calc . . R
C2 C -0.11459(14) 0.8686(2) 0.14197(6) 0.0486(5) Uani 1 d . . .
H2 H -0.1763 0.8386 0.1310 0.058 Uiso 1 calc . . R
C3 C -0.11732(15) 0.9442(2) 0.17473(6) 0.0515(5) Uani 1 d . . .
H3 H -0.1804 0.9641 0.1859 0.062 Uiso 1 calc . . R
C4 C -0.02945(14) 0.9890(2) 0.19058(5) 0.0443(5) Uani 1 d . . .
H4 H -0.0317 1.0393 0.2129 0.053 Uiso 1 calc . . R
C5 C 0.06506(13) 0.96200(17) 0.17425(5) 0.0340(4) Uani 1 d . . .
C6 C 0.06731(13) 0.88494(17) 0.14108(5) 0.0316(4) Uani 1 d . . .
C7 C 0.16409(12) 0.86430(16) 0.12523(4) 0.0284(4) Uani 1 d . . .
C8 C 0.25181(12) 0.91992(16) 0.13986(4) 0.0294(4) Uani 1 d . . .
C9 C 0.24877(13) 0.99164(17) 0.17363(5) 0.0343(4) Uani 1 d . . .
H9 H 0.3091 1.0258 0.1847 0.041 Uiso 1 calc . . R
C10 C 0.15783(13) 1.01059(18) 0.18984(5) 0.0364(4) Uani 1 d . . .
H10 H 0.1559 1.0584 0.2126 0.044 Uiso 1 calc . . R
C11 C 0.18924(13) 0.78890(17) 0.09155(5) 0.0310(4) Uani 1 d . . .
C12 C 0.33750(12) 0.87846(17) 0.11705(4) 0.0311(4) Uani 1 d . . .
C13 C 0.34097(12) 0.77744(18) 0.05358(5) 0.0319(4) Uani 1 d . . .
C14 C 0.36285(13) 0.64999(19) 0.04005(5) 0.0370(4) Uani 1 d . . .
H14 H 0.3478 0.5710 0.0542 0.044 Uiso 1 calc . . R
C15 C 0.40680(14) 0.6369(2) 0.00586(5) 0.0444(5) Uani 1 d . . .
H15 H 0.4200 0.5484 -0.0036 0.053 Uiso 1 calc . . R
C16 C 0.43197(14) 0.7507(2) -0.01490(5) 0.0479(5) Uani 1 d . . .
C17 C 0.40674(15) 0.8781(2) -0.00111(5) 0.0467(5) Uani 1 d . . .
H17 H 0.4211 0.9573 -0.0152 0.056 Uiso 1 calc . . R
C18 C 0.36130(14) 0.89217(19) 0.03266(5) 0.0395(4) Uani 1 d . . .
H18 H 0.3440 0.9802 0.0415 0.047 Uiso 1 calc . . R
C19 C 0.48487(19) 0.7378(3) -0.05137(6) 0.0760(8) Uani 1 d . . .
H19A H 0.5237 0.6526 -0.0518 0.114 Uiso 1 calc . . GR
H19B H 0.5308 0.8153 -0.0546 0.114 Uiso 1 calc . . GR
H19C H 0.4344 0.7371 -0.0714 0.114 Uiso 1 calc . . GR
C20 C 0.43852(12) 0.90293(17) 0.12165(4) 0.0320(4) Uani 1 d . . .
C21 C 0.51806(13) 0.8157(2) 0.10495(5) 0.0367(4) Uani 1 d . . .
C22 C 0.51474(15) 0.6742(2) 0.10801(5) 0.0462(5) Uani 1 d . . .
H22 H 0.4586 0.6324 0.1196 0.055 Uiso 1 calc . . R
C23 C 0.59148(17) 0.5935(3) 0.09449(6) 0.0609(6) Uani 1 d . . .
H23 H 0.5889 0.4972 0.0976 0.073 Uiso 1 calc . . R
C24 C 0.67133(18) 0.6517(3) 0.07660(6) 0.0704(8) Uani 1 d . . .
H24 H 0.7231 0.5958 0.0667 0.084 Uiso 1 calc . . R
C25 C 0.67639(17) 0.7912(3) 0.07306(6) 0.0696(7) Uani 1 d . . .
H25 H 0.7317 0.8316 0.0606 0.084 Uiso 1 calc . . R
C26 C 0.60099(15) 0.8735(2) 0.08761(5) 0.0522(5) Uani 1 d . . .
H26 H 0.6062 0.9700 0.0857 0.063 Uiso 1 calc . . R
C27 C 0.47548(12) 1.02090(18) 0.14350(4) 0.0337(4) Uani 1 d . . .
C28 C 0.55784(14) 1.0079(2) 0.16783(5) 0.0453(5) Uani 1 d . . .
H28 H 0.5881 0.9209 0.1716 0.054 Uiso 1 calc . . R
C29 C 0.59546(16) 1.1196(2) 0.18638(6) 0.0582(6) Uani 1 d . . .
H29 H 0.6507 1.1091 0.2032 0.070 Uiso 1 calc . . R
C30 C 0.55341(17) 1.2468(2) 0.18075(6) 0.0573(6) Uani 1 d . . .
H30 H 0.5802 1.3238 0.1934 0.069 Uiso 1 calc . . R
C31 C 0.47214(15) 1.2624(2) 0.15667(6) 0.0479(5) Uani 1 d . . .
H31 H 0.4430 1.3500 0.1528 0.057 Uiso 1 calc . . R
C32 C 0.43358(13) 1.14975(18) 0.13832(5) 0.0373(4) Uani 1 d . . .
H32 H 0.3776 1.1606 0.1219 0.045 Uiso 1 calc . . R
O2 O 0.29749(9) 0.47480(13) 0.12774(3) 0.0461(3) Uani 1 d . . .
N2 N 0.12421(10) 0.43620(14) 0.12512(4) 0.0330(3) Uani 1 d . . .
C33 C 0.35019(14) 0.65189(19) 0.19645(5) 0.0427(5) Uani 1 d . . .
H33 H 0.3852 0.6064 0.1773 0.051 Uiso 1 calc . . R
C34 C 0.40253(16) 0.7334(2) 0.22075(6) 0.0502(5) Uani 1 d . . .
H34 H 0.4736 0.7444 0.2181 0.060 Uiso 1 calc . . R
C35 C 0.35284(17) 0.8007(2) 0.24939(6) 0.0502(5) Uani 1 d . . .
H35 H 0.3900 0.8579 0.2658 0.060 Uiso 1 calc . . R
C36 C 0.25119(16) 0.78416(19) 0.25374(5) 0.0455(5) Uani 1 d . . .
H36 H 0.2183 0.8287 0.2735 0.055 Uiso 1 calc . . R
C37 C 0.19396(15) 0.70140(17) 0.22917(5) 0.0380(4) Uani 1 d . . .
C38 C 0.24465(14) 0.63538(17) 0.19979(5) 0.0363(4) Uani 1 d . . .
C39 C 0.18305(13) 0.55831(17) 0.17482(4) 0.0324(4) Uani 1 d . . .
C40 C 0.07947(13) 0.54480(17) 0.17882(4) 0.0320(4) Uani 1 d . . .
C41 C 0.03019(14) 0.61329(18) 0.20788(5) 0.0376(4) Uani 1 d . . .
H41 H -0.0412 0.6074 0.2104 0.045 Uiso 1 calc . . R
C42 C 0.08714(15) 0.68787(18) 0.23210(5) 0.0409(5) Uani 1 d . . .
H42 H 0.0541 0.7327 0.2518 0.049 Uiso 1 calc . . R
C43 C 0.21311(13) 0.48842(18) 0.14082(5) 0.0353(4) Uani 1 d . . .
C44 C 0.03892(13) 0.46533(17) 0.14731(4) 0.0315(4) Uani 1 d . . .
C45 C 0.12867(12) 0.34332(17) 0.09457(4) 0.0314(4) Uani 1 d . . .
C46 C 0.16780(13) 0.38748(19) 0.06164(5) 0.0376(4) Uani 1 d . . .
H46 H 0.1920 0.4783 0.0593 0.045 Uiso 1 calc . . R
C47 C 0.17165(14) 0.2989(2) 0.03199(5) 0.0426(5) Uani 1 d . . .
H47 H 0.2009 0.3291 0.0096 0.051 Uiso 1 calc . . R
C48 C 0.13371(13) 0.16688(19) 0.03423(5) 0.0391(4) Uani 1 d . . .
C49 C 0.09482(14) 0.12527(18) 0.06759(5) 0.0392(4) Uani 1 d . . .
H49 H 0.0683 0.0355 0.0698 0.047 Uiso 1 calc . . R
C50 C 0.09353(14) 0.21086(18) 0.09795(5) 0.0372(4) Uani 1 d . . .
H50 H 0.0688 0.1790 0.1209 0.045 Uiso 1 calc . . R
C51 C 0.13308(17) 0.0732(2) 0.00124(6) 0.0562(6) Uani 1 d . . .
H51A H 0.1064 -0.0162 0.0083 0.084 Uiso 1 calc . . GR
H51B H 0.2023 0.0627 -0.0078 0.084 Uiso 1 calc . . GR
H51C H 0.0902 0.1124 -0.0183 0.084 Uiso 1 calc . . GR
C52 C -0.05959(13) 0.43438(17) 0.13968(5) 0.0331(4) Uani 1 d . . .
C53 C -0.09895(12) 0.38961(18) 0.10304(5) 0.0338(4) Uani 1 d . . .
C54 C -0.07052(13) 0.45510(19) 0.07093(5) 0.0375(4) Uani 1 d . . .
H54 H -0.0268 0.5320 0.0722 0.045 Uiso 1 calc . . R
C55 C -0.10570(14) 0.4087(2) 0.03693(5) 0.0458(5) Uani 1 d . . .
H55 H -0.0858 0.4540 0.0150 0.055 Uiso 1 calc . . R
C56 C -0.16924(15) 0.2973(2) 0.03481(6) 0.0535(6) Uani 1 d . . .
H56 H -0.1916 0.2644 0.0115 0.064 Uiso 1 calc . . R
C57 C -0.20016(16) 0.2341(2) 0.06646(6) 0.0554(6) Uani 1 d . . .
H57 H -0.2448 0.1583 0.0650 0.067 Uiso 1 calc . . R
C58 C -0.16652(14) 0.2805(2) 0.10053(5) 0.0469(5) Uani 1 d . . .
H58 H -0.1897 0.2377 0.1223 0.056 Uiso 1 calc . . R
C59 C -0.13601(13) 0.44609(18) 0.16932(5) 0.0346(4) Uani 1 d . . .
C60 C -0.21663(14) 0.5366(2) 0.16588(5) 0.0438(5) Uani 1 d . . .
H60 H -0.2256 0.5865 0.1436 0.053 Uiso 1 calc . . R
C61 C -0.28402(15) 0.5552(2) 0.19431(6) 0.0560(6) Uani 1 d . . .
H61 H -0.3376 0.6194 0.1918 0.067 Uiso 1 calc . . R
C62 C -0.27365(17) 0.4809(3) 0.22621(6) 0.0622(7) Uani 1 d . . .
H62 H -0.3193 0.4948 0.2459 0.075 Uiso 1 calc . . R
C63 C -0.19722(18) 0.3863(2) 0.22962(6) 0.0586(6) Uani 1 d . . .
H63 H -0.1915 0.3329 0.2514 0.070 Uiso 1 calc . . R
C64 C -0.12842(15) 0.3685(2) 0.20144(5) 0.0450(5) Uani 1 d . . .
H64 H -0.0757 0.3031 0.2041 0.054 Uiso 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
O1 C11 1.2256(19) . ?
N1 C11 1.401(2) . ?
N1 C12 1.425(2) . ?
N1 C13 1.432(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.366(3) . ?
C1 C6 1.417(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.402(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.362(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.413(2) . ?
C5 C6 1.422(2) . ?
C5 C10 1.425(2) . ?
C6 C7 1.422(2) . ?
C7 C8 1.380(2) . ?
C7 C11 1.470(2) . ?
C8 C9 1.414(2) . ?
C8 C12 1.467(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.356(2) . ?
C10 H10 0.9500 . ?
C12 C20 1.364(2) . ?
C13 C14 1.374(2) . ?
C13 C18 1.385(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.382(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.388(3) . ?
C16 C17 1.387(3) . ?
C16 C19 1.509(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.378(3) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.489(2) . ?
C20 C27 1.481(2) . ?
C21 C22 1.391(3) . ?
C21 C26 1.390(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.380(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.369(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.375(4) . ?
C25 H25 0.9500 . ?
C25 C26 1.390(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.399(2) . ?
C27 C32 1.390(2) . ?
C28 H28 0.9500 . ?
C28 C29 1.375(3) . ?
C29 H29 0.9500 . ?
C29 C30 1.378(3) . ?
C30 H30 0.9500 . ?
C30 C31 1.385(3) . ?
C31 H31 0.9500 . ?
C31 C32 1.383(3) . ?
C32 H32 0.9500 . ?
O2 C43 1.224(2) . ?
N2 C43 1.396(2) . ?
N2 C44 1.421(2) . ?
N2 C45 1.436(2) . ?
C33 H33 0.9500 . ?
C33 C34 1.371(3) . ?
C33 C38 1.410(3) . ?
C34 H34 0.9500 . ?
C34 C35 1.401(3) . ?
C35 H35 0.9500 . ?
C35 C36 1.363(3) . ?
C36 H36 0.9500 . ?
C36 C37 1.417(2) . ?
C37 C38 1.421(3) . ?
C37 C42 1.422(3) . ?
C38 C39 1.427(2) . ?
C39 C40 1.384(2) . ?
C39 C43 1.470(2) . ?
C40 C41 1.415(2) . ?
C40 C44 1.479(2) . ?
C41 H41 0.9500 . ?
C41 C42 1.363(2) . ?
C42 H42 0.9500 . ?
C44 C52 1.361(2) . ?
C45 C46 1.378(2) . ?
C45 C50 1.384(2) . ?
C46 H46 0.9500 . ?
C46 C47 1.383(3) . ?
C47 H47 0.9500 . ?
C47 C48 1.390(3) . ?
C48 C49 1.383(2) . ?
C48 C51 1.509(3) . ?
C49 H49 0.9500 . ?
C49 C50 1.385(2) . ?
C50 H50 0.9500 . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C52 C53 1.488(2) . ?
C52 C59 1.488(2) . ?
C53 C54 1.386(2) . ?
C53 C58 1.395(2) . ?
C54 H54 0.9500 . ?
C54 C55 1.390(2) . ?
C55 H55 0.9500 . ?
C55 C56 1.378(3) . ?
C56 H56 0.9500 . ?
C56 C57 1.371(3) . ?
C57 H57 0.9500 . ?
C57 C58 1.386(3) . ?
C58 H58 0.9500 . ?
C59 C60 1.390(3) . ?
C59 C64 1.394(2) . ?
C60 H60 0.9500 . ?
C60 C61 1.383(3) . ?
C61 H61 0.9500 . ?
C61 C62 1.373(3) . ?
C62 H62 0.9500 . ?
C62 C63 1.375(3) . ?
C63 H63 0.9500 . ?
C63 C64 1.387(3) . ?
C64 H64 0.9500 . ?

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
C11 N1 C12 110.92(13) . . ?
C11 N1 C13 119.54(13) . . ?
C12 N1 C13 122.82(13) . . ?
C2 C1 H1 120.1 . . ?
C2 C1 C6 119.83(18) . . ?
C6 C1 H1 120.1 . . ?
C1 C2 H2 119.3 . . ?
C1 C2 C3 121.37(18) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.90(18) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 120.98(18) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 118.83(16) . . ?
C4 C5 C10 122.03(16) . . ?
C6 C5 C10 119.14(16) . . ?
C1 C6 C5 119.06(16) . . ?
C1 C6 C7 124.42(16) . . ?
C5 C6 C7 116.49(15) . . ?
C6 C7 C11 128.39(15) . . ?
C8 C7 C6 122.83(15) . . ?
C8 C7 C11 108.75(14) . . ?
C7 C8 C9 119.82(16) . . ?
C7 C8 C12 108.84(14) . . ?
C9 C8 C12 131.04(15) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 C8 118.58(16) . . ?
C10 C9 H9 120.7 . . ?
C5 C10 H10 118.5 . . ?
C9 C10 C5 122.93(16) . . ?
C9 C10 H10 118.5 . . ?
O1 C11 N1 123.99(16) . . ?
O1 C11 C7 130.07(16) . . ?
N1 C11 C7 105.92(14) . . ?
N1 C12 C8 105.37(13) . . ?
C20 C12 N1 124.55(15) . . ?
C20 C12 C8 129.95(15) . . ?
C14 C13 N1 121.30(16) . . ?
C14 C13 C18 119.92(16) . . ?
C18 C13 N1 118.76(15) . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.83(18) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.4 . . ?
C14 C15 C16 121.28(18) . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C19 121.7(2) . . ?
C17 C16 C15 117.80(18) . . ?
C17 C16 C19 120.5(2) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 C16 121.35(18) . . ?
C18 C17 H17 119.3 . . ?
C13 C18 H18 120.1 . . ?
C17 C18 C13 119.73(18) . . ?
C17 C18 H18 120.1 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C12 C20 C21 122.89(15) . . ?
C12 C20 C27 121.22(16) . . ?
C27 C20 C21 115.89(14) . . ?
C22 C21 C20 121.09(17) . . ?
C26 C21 C20 120.89(18) . . ?
C26 C21 C22 117.91(18) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 C21 121.2(2) . . ?
C23 C22 H22 119.4 . . ?
C22 C23 H23 119.9 . . ?
C24 C23 C22 120.2(2) . . ?
C24 C23 H23 119.9 . . ?
C23 C24 H24 120.1 . . ?
C23 C24 C25 119.8(2) . . ?
C25 C24 H24 120.1 . . ?
C24 C25 H25 119.8 . . ?
C24 C25 C26 120.4(2) . . ?
C26 C25 H25 119.8 . . ?
C21 C26 H26 119.8 . . ?
C25 C26 C21 120.5(2) . . ?
C25 C26 H26 119.8 . . ?
C28 C27 C20 121.05(16) . . ?
C32 C27 C20 120.53(14) . . ?
C32 C27 C28 118.26(17) . . ?
C27 C28 H28 119.7 . . ?
C29 C28 C27 120.69(19) . . ?
C29 C28 H28 119.7 . . ?
C28 C29 H29 119.9 . . ?
C28 C29 C30 120.29(18) . . ?
C30 C29 H29 119.9 . . ?
C29 C30 H30 119.9 . . ?
C29 C30 C31 120.10(19) . . ?
C31 C30 H30 119.9 . . ?
C30 C31 H31 120.2 . . ?
C32 C31 C30 119.59(19) . . ?
C32 C31 H31 120.2 . . ?
C27 C32 H32 119.5 . . ?
C31 C32 C27 121.06(16) . . ?
C31 C32 H32 119.5 . . ?
C43 N2 C44 111.31(13) . . ?
C43 N2 C45 120.35(14) . . ?
C44 N2 C45 127.21(13) . . ?
C34 C33 H33 119.9 . . ?
C34 C33 C38 120.2(2) . . ?
C38 C33 H33 119.9 . . ?
C33 C34 H34 119.5 . . ?
C33 C34 C35 121.0(2) . . ?
C35 C34 H34 119.5 . . ?
C34 C35 H35 120.0 . . ?
C36 C35 C34 120.04(18) . . ?
C36 C35 H35 120.0 . . ?
C35 C36 H36 119.5 . . ?
C35 C36 C37 120.9(2) . . ?
C37 C36 H36 119.5 . . ?
C36 C37 C38 118.70(18) . . ?
C36 C37 C42 121.88(19) . . ?
C38 C37 C42 119.35(16) . . ?
C33 C38 C37 119.15(16) . . ?
C33 C38 C39 124.26(18) . . ?
C37 C38 C39 116.58(16) . . ?
C38 C39 C43 128.48(16) . . ?
C40 C39 C38 122.75(17) . . ?
C40 C39 C43 108.69(14) . . ?
C39 C40 C41 119.78(15) . . ?
C39 C40 C44 108.58(15) . . ?
C41 C40 C44 131.36(16) . . ?
C40 C41 H41 120.7 . . ?
C42 C41 C40 118.70(17) . . ?
C42 C41 H41 120.7 . . ?
C37 C42 H42 118.6 . . ?
C41 C42 C37 122.81(18) . . ?
C41 C42 H42 118.6 . . ?
O2 C43 N2 124.55(16) . . ?
O2 C43 C39 129.24(16) . . ?
N2 C43 C39 106.22(15) . . ?
N2 C44 C40 105.18(13) . . ?
C52 C44 N2 127.01(15) . . ?
C52 C44 C40 127.67(16) . . ?
C46 C45 N2 119.37(15) . . ?
C46 C45 C50 120.06(16) . . ?
C50 C45 N2 120.57(15) . . ?
C45 C46 H46 120.1 . . ?
C45 C46 C47 119.72(17) . . ?
C47 C46 H46 120.1 . . ?
C46 C47 H47 119.3 . . ?
C46 C47 C48 121.43(17) . . ?
C48 C47 H47 119.3 . . ?
C47 C48 C51 121.21(17) . . ?
C49 C48 C47 117.61(17) . . ?
C49 C48 C51 121.17(18) . . ?
C48 C49 H49 119.1 . . ?
C48 C49 C50 121.78(17) . . ?
C50 C49 H49 119.1 . . ?
C45 C50 C49 119.33(17) . . ?
C45 C50 H50 120.3 . . ?
C49 C50 H50 120.3 . . ?
C48 C51 H51A 109.5 . . ?
C48 C51 H51B 109.5 . . ?
C48 C51 H51C 109.5 . . ?
H51A C51 H51B 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C44 C52 C53 124.76(16) . . ?
C44 C52 C59 119.38(15) . . ?
C59 C52 C53 115.86(14) . . ?
C54 C53 C52 121.33(15) . . ?
C54 C53 C58 118.64(16) . . ?
C58 C53 C52 120.03(16) . . ?
C53 C54 H54 119.9 . . ?
C53 C54 C55 120.28(18) . . ?
C55 C54 H54 119.9 . . ?
C54 C55 H55 119.8 . . ?
C56 C55 C54 120.36(19) . . ?
C56 C55 H55 119.8 . . ?
C55 C56 H56 120.1 . . ?
C57 C56 C55 119.86(18) . . ?
C57 C56 H56 120.1 . . ?
C56 C57 H57 119.9 . . ?
C56 C57 C58 120.28(19) . . ?
C58 C57 H57 119.9 . . ?
C53 C58 H58 119.7 . . ?
C57 C58 C53 120.51(19) . . ?
C57 C58 H58 119.7 . . ?
C60 C59 C52 120.63(16) . . ?
C60 C59 C64 118.03(18) . . ?
C64 C59 C52 121.33(17) . . ?
C59 C60 H60 119.5 . . ?
C61 C60 C59 121.06(19) . . ?
C61 C60 H60 119.5 . . ?
C60 C61 H61 120.0 . . ?
C62 C61 C60 120.1(2) . . ?
C62 C61 H61 120.0 . . ?
C61 C62 H62 120.0 . . ?
C61 C62 C63 119.9(2) . . ?
C63 C62 H62 120.0 . . ?
C62 C63 H63 119.8 . . ?
C62 C63 C64 120.3(2) . . ?
C64 C63 H63 119.8 . . ?
C59 C64 H64 119.8 . . ?
C63 C64 C59 120.5(2) . . ?
C63 C64 H64 119.8 . . ?

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
N1 C12 C20 C21 -18.1(3) . . . . ?
N1 C12 C20 C27 161.06(15) . . . . ?
N1 C13 C14 C15 179.62(15) . . . . ?
N1 C13 C18 C17 179.22(15) . . . . ?
C1 C2 C3 C4 0.6(3) . . . . ?
C1 C6 C7 C8 175.52(16) . . . . ?
C1 C6 C7 C11 -2.2(3) . . . . ?
C2 C1 C6 C5 1.5(3) . . . . ?
C2 C1 C6 C7 -176.64(17) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C3 C4 C5 C10 178.49(17) . . . . ?
C4 C5 C6 C1 -0.2(2) . . . . ?
C4 C5 C6 C7 178.12(15) . . . . ?
C4 C5 C10 C9 -176.59(17) . . . . ?
C5 C6 C7 C8 -2.7(2) . . . . ?
C5 C6 C7 C11 179.59(15) . . . . ?
C6 C1 C2 C3 -1.8(3) . . . . ?
C6 C5 C10 C9 2.8(3) . . . . ?
C6 C7 C8 C9 5.3(2) . . . . ?
C6 C7 C8 C12 179.76(14) . . . . ?
C6 C7 C11 O1 4.0(3) . . . . ?
C6 C7 C11 N1 -177.84(16) . . . . ?
C7 C8 C9 C10 -3.7(2) . . . . ?
C7 C8 C12 N1 -0.72(17) . . . . ?
C7 C8 C12 C20 -176.52(17) . . . . ?
C8 C7 C11 O1 -173.93(17) . . . . ?
C8 C7 C11 N1 4.18(18) . . . . ?
C8 C9 C10 C5 -0.3(3) . . . . ?
C8 C12 C20 C21 156.99(17) . . . . ?
C8 C12 C20 C27 -23.9(3) . . . . ?
C9 C8 C12 N1 172.89(16) . . . . ?
C9 C8 C12 C20 -2.9(3) . . . . ?
C10 C5 C6 C1 -179.64(16) . . . . ?
C10 C5 C6 C7 -1.3(2) . . . . ?
C11 N1 C12 C8 3.46(17) . . . . ?
C11 N1 C12 C20 179.56(16) . . . . ?
C11 N1 C13 C14 -85.9(2) . . . . ?
C11 N1 C13 C18 92.58(19) . . . . ?
C11 C7 C8 C9 -176.57(14) . . . . ?
C11 C7 C8 C12 -2.12(18) . . . . ?
C12 N1 C11 O1 173.55(15) . . . . ?
C12 N1 C11 C7 -4.71(17) . . . . ?
C12 N1 C13 C14 125.48(17) . . . . ?
C12 N1 C13 C18 -56.1(2) . . . . ?
C12 C8 C9 C10 -176.73(17) . . . . ?
C12 C20 C21 C22 -48.4(2) . . . . ?
C12 C20 C21 C26 135.29(18) . . . . ?
C12 C20 C27 C28 138.20(18) . . . . ?
C12 C20 C27 C32 -46.5(2) . . . . ?
C13 N1 C11 O1 21.5(2) . . . . ?
C13 N1 C11 C7 -156.80(14) . . . . ?
C13 N1 C12 C8 154.48(14) . . . . ?
C13 N1 C12 C20 -29.4(2) . . . . ?
C13 C14 C15 C16 1.7(3) . . . . ?
C14 C13 C18 C17 -2.3(3) . . . . ?
C14 C15 C16 C17 -3.3(3) . . . . ?
C14 C15 C16 C19 176.79(18) . . . . ?
C15 C16 C17 C18 2.2(3) . . . . ?
C16 C17 C18 C13 0.6(3) . . . . ?
C18 C13 C14 C15 1.2(3) . . . . ?
C19 C16 C17 C18 -177.94(18) . . . . ?
C20 C21 C22 C23 -176.07(16) . . . . ?
C20 C21 C26 C25 178.08(17) . . . . ?
C20 C27 C28 C29 176.14(18) . . . . ?
C20 C27 C32 C31 -175.43(17) . . . . ?
C21 C20 C27 C28 -42.6(2) . . . . ?
C21 C20 C27 C32 132.75(17) . . . . ?
C21 C22 C23 C24 -2.1(3) . . . . ?
C22 C21 C26 C25 1.7(3) . . . . ?
C22 C23 C24 C25 1.9(3) . . . . ?
C23 C24 C25 C26 0.1(3) . . . . ?
C24 C25 C26 C21 -1.9(3) . . . . ?
C26 C21 C22 C23 0.4(3) . . . . ?
C27 C20 C21 C22 132.41(17) . . . . ?
C27 C20 C21 C26 -43.9(2) . . . . ?
C27 C28 C29 C30 -1.1(3) . . . . ?
C28 C27 C32 C31 0.0(3) . . . . ?
C28 C29 C30 C31 0.8(3) . . . . ?
C29 C30 C31 C32 0.0(3) . . . . ?
C30 C31 C32 C27 -0.4(3) . . . . ?
C32 C27 C28 C29 0.7(3) . . . . ?
N2 C44 C52 C53 -13.4(3) . . . . ?
N2 C44 C52 C59 167.19(15) . . . . ?
N2 C45 C46 C47 -179.51(15) . . . . ?
N2 C45 C50 C49 177.30(15) . . . . ?
C33 C34 C35 C36 0.9(3) . . . . ?
C33 C38 C39 C40 -179.65(17) . . . . ?
C33 C38 C39 C43 -3.3(3) . . . . ?
C34 C33 C38 C37 -1.6(3) . . . . ?
C34 C33 C38 C39 176.79(16) . . . . ?
C34 C35 C36 C37 -1.2(3) . . . . ?
C35 C36 C37 C38 0.1(3) . . . . ?
C35 C36 C37 C42 -176.94(17) . . . . ?
C36 C37 C38 C33 1.3(2) . . . . ?
C36 C37 C38 C39 -177.22(15) . . . . ?
C36 C37 C42 C41 177.27(16) . . . . ?
C37 C38 C39 C40 -1.2(2) . . . . ?
C37 C38 C39 C43 175.13(16) . . . . ?
C38 C33 C34 C35 0.5(3) . . . . ?
C38 C37 C42 C41 0.2(3) . . . . ?
C38 C39 C40 C41 2.4(2) . . . . ?
C38 C39 C40 C44 176.94(14) . . . . ?
C38 C39 C43 O2 4.5(3) . . . . ?
C38 C39 C43 N2 -175.93(16) . . . . ?
C39 C40 C41 C42 -2.1(2) . . . . ?
C39 C40 C44 N2 -0.73(18) . . . . ?
C39 C40 C44 C52 -176.68(17) . . . . ?
C40 C39 C43 O2 -178.71(18) . . . . ?
C40 C39 C43 N2 0.83(18) . . . . ?
C40 C41 C42 C37 0.9(3) . . . . ?
C40 C44 C52 C53 161.70(16) . . . . ?
C40 C44 C52 C59 -17.7(3) . . . . ?
C41 C40 C44 N2 172.99(17) . . . . ?
C41 C40 C44 C52 -3.0(3) . . . . ?
C42 C37 C38 C33 178.42(16) . . . . ?
C42 C37 C38 C39 -0.1(2) . . . . ?
C43 N2 C44 C40 1.29(18) . . . . ?
C43 N2 C44 C52 177.28(16) . . . . ?
C43 N2 C45 C46 -63.9(2) . . . . ?
C43 N2 C45 C50 116.52(18) . . . . ?
C43 C39 C40 C41 -174.62(14) . . . . ?
C43 C39 C40 C44 -0.05(18) . . . . ?
C44 N2 C43 O2 178.23(16) . . . . ?
C44 N2 C43 C39 -1.33(18) . . . . ?
C44 N2 C45 C46 129.34(18) . . . . ?
C44 N2 C45 C50 -50.3(2) . . . . ?
C44 C40 C41 C42 -175.28(16) . . . . ?
C44 C52 C53 C54 -45.0(3) . . . . ?
C44 C52 C53 C58 135.57(19) . . . . ?
C44 C52 C59 C60 118.29(18) . . . . ?
C44 C52 C59 C64 -60.8(2) . . . . ?
C45 N2 C43 O2 9.5(3) . . . . ?
C45 N2 C43 C39 -170.05(13) . . . . ?
C45 N2 C44 C40 169.06(14) . . . . ?
C45 N2 C44 C52 -15.0(3) . . . . ?
C45 C46 C47 C48 2.2(3) . . . . ?
C46 C45 C50 C49 -2.3(3) . . . . ?
C46 C47 C48 C49 -2.1(3) . . . . ?
C46 C47 C48 C51 176.74(17) . . . . ?
C47 C48 C49 C50 -0.2(3) . . . . ?
C48 C49 C50 C45 2.4(3) . . . . ?
C50 C45 C46 C47 0.1(3) . . . . ?
C51 C48 C49 C50 -179.02(17) . . . . ?
C52 C53 C54 C55 177.91(16) . . . . ?
C52 C53 C58 C57 -177.14(18) . . . . ?
C52 C59 C60 C61 -175.46(17) . . . . ?
C52 C59 C64 C63 176.43(17) . . . . ?
C53 C52 C59 C60 -61.2(2) . . . . ?
C53 C52 C59 C64 119.71(18) . . . . ?
C53 C54 C55 C56 0.1(3) . . . . ?
C54 C53 C58 C57 3.4(3) . . . . ?
C54 C55 C56 C57 1.8(3) . . . . ?
C55 C56 C57 C58 -1.0(3) . . . . ?
C56 C57 C58 C53 -1.6(3) . . . . ?
C58 C53 C54 C55 -2.6(3) . . . . ?
C59 C52 C53 C54 134.43(17) . . . . ?
C59 C52 C53 C58 -45.0(2) . . . . ?
C59 C60 C61 C62 -1.8(3) . . . . ?
C60 C59 C64 C63 -2.7(3) . . . . ?
C60 C61 C62 C63 -1.1(3) . . . . ?
C61 C62 C63 C64 2.1(3) . . . . ?
C62 C63 C64 C59 -0.1(3) . . . . ?
C64 C59 C60 C61 3.7(3) . . . . ?

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

data_151020_zxr454_013
_database_code_depnum_ccdc_archive 'CCDC 1436545'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2016-08-02 downloaded from the CCDC.
;
_audit_creation_date             2015-10-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C44 H31 N O'
_chemical_formula_sum            'C44 H31 N O'
_chemical_formula_weight         589.70
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2 o8'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.7155(5)
_cell_length_b                   11.1424(6)
_cell_length_c                   33.670(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.871(6)
_cell_angle_gamma                90.00
_cell_volume                     3631.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2520
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.6043
_cell_measurement_theta_min      3.1049
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.079
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.26
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            14478
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.54
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0319913000
_diffrn_orient_matrix_UB_12      -0.0409325000
_diffrn_orient_matrix_UB_13      -0.0124688000
_diffrn_orient_matrix_UB_21      0.0439793000
_diffrn_orient_matrix_UB_22      -0.0198610000
_diffrn_orient_matrix_UB_23      0.0165994000
_diffrn_orient_matrix_UB_31      -0.0490555000
_diffrn_orient_matrix_UB_32      -0.0445124000
_diffrn_orient_matrix_UB_33      0.0040642000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                4221
_reflns_number_total             6614
_reflns_odcompleteness_completeness 99.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         6614
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1051
_refine_ls_R_factor_gt           0.0676
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1012P)²+0.2052P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1744
_refine_ls_wR_factor_ref         0.1950
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C14(H14), C15(H15),
 C17(H17), C18(H18), C22(H22), C23(H23), C25(H25), C26(H26), C28(H28), C29(H29),
  C30(H30), C31(H31), C32(H32), C34(H34), C35(H35), C37(H37), C38(H38),
 C40(H40), C41(H41), C42(H42), C43(H43), C44(H44)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.3621(2) 0.60694(16) 0.13294(6) 0.0671(5) Uani 1 d . . .
N1 N 0.45878(19) 0.77444(16) 0.16531(5) 0.0454(5) Uani 1 d . . .
C1 C 0.3642(2) 0.3952(2) 0.19181(9) 0.0595(7) Uani 1 d . . .
H1 H 0.3512 0.4076 0.1644 0.071 Uiso 1 calc . . R
C2 C 0.3421(3) 0.2850(2) 0.20715(12) 0.0739(9) Uani 1 d . . .
H2 H 0.3130 0.2226 0.1901 0.089 Uiso 1 calc . . R
C3 C 0.3624(3) 0.2638(3) 0.24805(13) 0.0808(10) Uani 1 d . . .
H3 H 0.3452 0.1880 0.2580 0.097 Uiso 1 calc . . R
C4 C 0.4070(3) 0.3530(3) 0.27340(10) 0.0735(9) Uani 1 d . . .
H4 H 0.4227 0.3373 0.3005 0.088 Uiso 1 calc . . R
C5 C 0.4298(2) 0.4703(2) 0.25876(8) 0.0547(7) Uani 1 d . . .
C6 C 0.4072(2) 0.4916(2) 0.21756(8) 0.0500(6) Uani 1 d . . .
C7 C 0.4299(2) 0.6100(2) 0.20407(7) 0.0441(6) Uani 1 d . . .
C8 C 0.4779(2) 0.7015(2) 0.22929(7) 0.0436(5) Uani 1 d . . .
C9 C 0.5056(2) 0.6778(2) 0.27045(7) 0.0537(6) Uani 1 d . . .
H9 H 0.5412 0.7372 0.2878 0.064 Uiso 1 calc . . R
C10 C 0.4786(2) 0.5653(2) 0.28414(8) 0.0607(7) Uani 1 d . . .
H10 H 0.4931 0.5505 0.3114 0.073 Uiso 1 calc . . R
C11 C 0.4115(2) 0.6553(2) 0.16314(7) 0.0475(6) Uani 1 d . . .
C12 C 0.5031(2) 0.8077(2) 0.20520(7) 0.0428(5) Uani 1 d . . .
C13 C 0.4116(2) 0.8571(2) 0.13451(7) 0.0500(6) Uani 1 d . . .
C14 C 0.3266(3) 0.9501(2) 0.14250(9) 0.0687(8) Uani 1 d . . .
H14 H 0.3031 0.9631 0.1684 0.082 Uiso 1 calc . . R
C15 C 0.2756(4) 1.0249(3) 0.11175(13) 0.0969(12) Uani 1 d . . .
H15 H 0.2180 1.0880 0.1175 0.116 Uiso 1 calc . . R
C16 C 0.3069(5) 1.0090(3) 0.07350(12) 0.1015(12) Uani 1 d . . .
C17 C 0.3930(4) 0.9153(4) 0.06610(10) 0.0962(11) Uani 1 d . . .
H17 H 0.4167 0.9027 0.0402 0.115 Uiso 1 calc . . R
C18 C 0.4456(3) 0.8389(3) 0.09619(8) 0.0688(8) Uani 1 d . . .
H18 H 0.5034 0.7758 0.0905 0.083 Uiso 1 calc . . R
C19 C 0.2454(7) 1.0890(5) 0.04010(16) 0.182(3) Uani 1 d . . .
H19A H 0.3026 1.0865 0.0182 0.273 Uiso 1 calc . . GR
H19B H 0.2402 1.1700 0.0496 0.273 Uiso 1 calc . . GR
H19C H 0.1543 1.0612 0.0313 0.273 Uiso 1 calc . . GR
C20 C 0.5741(2) 0.9099(2) 0.21530(7) 0.0439(5) Uani 1 d . . .
C21 C 0.5835(2) 0.9564(2) 0.25666(7) 0.0427(5) Uani 1 d . . .
C22 C 0.4669(2) 0.96373(19) 0.27806(7) 0.0451(6) Uani 1 d . . .
H22 H 0.3837 0.9320 0.2670 0.054 Uiso 1 calc . . R
C23 C 0.4717(2) 1.0166(2) 0.31500(7) 0.0448(6) Uani 1 d . . .
H23 H 0.3922 1.0186 0.3285 0.054 Uiso 1 calc . . R
C24 C 0.5929(2) 1.0670(2) 0.33259(7) 0.0438(5) Uani 1 d . . .
C25 C 0.7090(2) 1.0579(2) 0.31170(7) 0.0570(7) Uani 1 d . . .
H25 H 0.7923 1.0891 0.3229 0.068 Uiso 1 calc . . R
C26 C 0.7047(2) 1.0039(2) 0.27468(8) 0.0569(7) Uani 1 d . . .
H26 H 0.7850 0.9993 0.2616 0.068 Uiso 1 calc . . R
C27 C 0.5952(2) 1.1307(2) 0.37123(7) 0.0473(6) Uani 1 d . . .
C28 C 0.4798(3) 1.1909(2) 0.38234(8) 0.0621(7) Uani 1 d . . .
H28 H 0.3994 1.1910 0.3653 0.075 Uiso 1 calc . . R
C29 C 0.4816(3) 1.2509(3) 0.41828(9) 0.0768(9) Uani 1 d . . .
H29 H 0.4028 1.2905 0.4252 0.092 Uiso 1 calc . . R
C30 C 0.5983(4) 1.2523(3) 0.44366(9) 0.0822(10) Uani 1 d . . .
H30 H 0.5993 1.2932 0.4678 0.099 Uiso 1 calc . . R
C31 C 0.7132(4) 1.1940(3) 0.43378(9) 0.0824(10) Uani 1 d . . .
H31 H 0.7926 1.1945 0.4513 0.099 Uiso 1 calc . . R
C32 C 0.7128(3) 1.1338(3) 0.39770(8) 0.0663(7) Uani 1 d . . .
H32 H 0.7925 1.0949 0.3912 0.080 Uiso 1 calc . . R
C33 C 0.6417(2) 0.9822(2) 0.18578(7) 0.0454(6) Uani 1 d . . .
C34 C 0.6381(2) 1.1066(2) 0.18587(7) 0.0507(6) Uani 1 d . . .
H34 H 0.5930 1.1464 0.2053 0.061 Uiso 1 calc . . R
C35 C 0.7000(3) 1.1723(2) 0.15770(8) 0.0592(7) Uani 1 d . . .
H35 H 0.6960 1.2557 0.1585 0.071 Uiso 1 calc . . R
C36 C 0.7681(3) 1.1166(2) 0.12821(7) 0.0591(7) Uani 1 d . . .
C37 C 0.7764(3) 0.9923(2) 0.12896(8) 0.0627(7) Uani 1 d . . .
H37 H 0.8245 0.9529 0.1101 0.075 Uiso 1 calc . . R
C38 C 0.7151(2) 0.9263(2) 0.15698(8) 0.0555(7) Uani 1 d . . .
H38 H 0.7225 0.8431 0.1568 0.067 Uiso 1 calc . . R
C39 C 0.8305(4) 1.1864(3) 0.09704(9) 0.0844(10) Uani 1 d . . .
C40 C 0.9084(5) 1.2888(3) 0.10618(12) 0.1123(15) Uani 1 d . . .
H40 H 0.9239 1.3131 0.1326 0.135 Uiso 1 calc . . R
C41 C 0.9632(6) 1.3553(4) 0.07666(15) 0.153(2) Uani 1 d . . .
H41 H 1.0157 1.4233 0.0832 0.184 Uiso 1 calc . . R
C42 C 0.9393(7) 1.3199(5) 0.03726(16) 0.168(3) Uani 1 d . . .
H42 H 0.9721 1.3665 0.0172 0.201 Uiso 1 calc . . R
C43 C 0.8677(7) 1.2169(6) 0.02780(15) 0.175(3) Uani 1 d . . .
H43 H 0.8556 1.1912 0.0015 0.210 Uiso 1 calc . . R
C44 C 0.8132(5) 1.1507(4) 0.05764(12) 0.1320(18) Uani 1 d . . .
H44 H 0.7641 1.0809 0.0510 0.158 Uiso 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
O1 C11 1.213(3) . ?
N1 C11 1.405(3) . ?
N1 C12 1.424(3) . ?
N1 C13 1.433(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.355(4) . ?
C1 C6 1.421(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.395(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.356(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.420(4) . ?
C5 C6 1.406(4) . ?
C5 C10 1.417(4) . ?
C6 C7 1.419(3) . ?
C7 C8 1.382(3) . ?
C7 C11 1.464(3) . ?
C8 C9 1.414(3) . ?
C8 C12 1.466(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.368(3) . ?
C10 H10 0.9300 . ?
C12 C20 1.360(3) . ?
C13 C14 1.365(4) . ?
C13 C18 1.374(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.388(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.360(6) . ?
C16 C17 1.374(5) . ?
C16 C19 1.518(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.387(4) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.481(3) . ?
C20 C33 1.476(3) . ?
C21 C22 1.396(3) . ?
C21 C26 1.383(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.373(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.391(3) . ?
C24 C25 1.383(3) . ?
C24 C27 1.480(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.382(3) . ?
C26 H26 0.9300 . ?
C27 C28 1.386(3) . ?
C27 C32 1.388(4) . ?
C28 H28 0.9300 . ?
C28 C29 1.381(4) . ?
C29 H29 0.9300 . ?
C29 C30 1.360(5) . ?
C30 H30 0.9300 . ?
C30 C31 1.357(5) . ?
C31 H31 0.9300 . ?
C31 C32 1.388(4) . ?
C32 H32 0.9300 . ?
C33 C34 1.387(3) . ?
C33 C38 1.398(3) . ?
C34 H34 0.9300 . ?
C34 C35 1.376(3) . ?
C35 H35 0.9300 . ?
C35 C36 1.387(3) . ?
C36 C37 1.387(4) . ?
C36 C39 1.477(4) . ?
C37 H37 0.9300 . ?
C37 C38 1.371(3) . ?
C38 H38 0.9300 . ?
C39 C40 1.389(4) . ?
C39 C44 1.382(5) . ?
C40 H40 0.9300 . ?
C40 C41 1.382(5) . ?
C41 H41 0.9300 . ?
C41 C42 1.384(7) . ?
C42 H42 0.9300 . ?
C42 C43 1.366(7) . ?
C43 H43 0.9300 . ?
C43 C44 1.387(6) . ?
C44 H44 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 N1 C12 111.48(18) . . ?
C11 N1 C13 119.13(19) . . ?
C12 N1 C13 124.59(18) . . ?
C2 C1 H1 120.0 . . ?
C2 C1 C6 120.0(3) . . ?
C6 C1 H1 120.0 . . ?
C1 C2 H2 119.5 . . ?
C1 C2 C3 121.1(3) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.5(3) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.4(3) . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 118.8(3) . . ?
C6 C5 C10 119.0(2) . . ?
C10 C5 C4 122.2(3) . . ?
C5 C6 C1 119.2(2) . . ?
C5 C6 C7 117.2(2) . . ?
C7 C6 C1 123.6(2) . . ?
C6 C7 C11 127.7(2) . . ?
C8 C7 C6 122.9(2) . . ?
C8 C7 C11 109.4(2) . . ?
C7 C8 C9 119.4(2) . . ?
C7 C8 C12 108.6(2) . . ?
C9 C8 C12 131.8(2) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 C8 118.4(2) . . ?
C10 C9 H9 120.8 . . ?
C5 C10 H10 118.5 . . ?
C9 C10 C5 123.0(2) . . ?
C9 C10 H10 118.5 . . ?
O1 C11 N1 124.6(2) . . ?
O1 C11 C7 130.1(2) . . ?
N1 C11 C7 105.3(2) . . ?
N1 C12 C8 105.11(18) . . ?
C20 C12 N1 124.0(2) . . ?
C20 C12 C8 130.0(2) . . ?
C14 C13 N1 120.5(2) . . ?
C14 C13 C18 119.7(2) . . ?
C18 C13 N1 119.8(2) . . ?
C13 C14 H14 120.3 . . ?
C13 C14 C15 119.5(3) . . ?
C15 C14 H14 120.3 . . ?
C14 C15 H15 118.8 . . ?
C16 C15 C14 122.3(4) . . ?
C16 C15 H15 118.8 . . ?
C15 C16 C17 117.3(3) . . ?
C15 C16 C19 121.3(5) . . ?
C17 C16 C19 121.3(4) . . ?
C16 C17 H17 119.1 . . ?
C16 C17 C18 121.7(3) . . ?
C18 C17 H17 119.1 . . ?
C13 C18 C17 119.5(3) . . ?
C13 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C12 C20 C21 121.15(19) . . ?
C12 C20 C33 122.3(2) . . ?
C33 C20 C21 116.54(18) . . ?
C22 C21 C20 121.17(19) . . ?
C26 C21 C20 121.91(19) . . ?
C26 C21 C22 116.7(2) . . ?
C21 C22 H22 119.1 . . ?
C23 C22 C21 121.7(2) . . ?
C23 C22 H22 119.1 . . ?
C22 C23 H23 119.3 . . ?
C22 C23 C24 121.4(2) . . ?
C24 C23 H23 119.3 . . ?
C23 C24 C27 121.15(19) . . ?
C25 C24 C23 116.9(2) . . ?
C25 C24 C27 122.0(2) . . ?
C24 C25 H25 119.1 . . ?
C26 C25 C24 121.8(2) . . ?
C26 C25 H25 119.1 . . ?
C21 C26 H26 119.2 . . ?
C25 C26 C21 121.5(2) . . ?
C25 C26 H26 119.2 . . ?
C28 C27 C24 121.1(2) . . ?
C28 C27 C32 117.1(2) . . ?
C32 C27 C24 121.8(2) . . ?
C27 C28 H28 119.3 . . ?
C29 C28 C27 121.3(3) . . ?
C29 C28 H28 119.3 . . ?
C28 C29 H29 119.9 . . ?
C30 C29 C28 120.3(3) . . ?
C30 C29 H29 119.9 . . ?
C29 C30 H30 120.0 . . ?
C31 C30 C29 120.0(3) . . ?
C31 C30 H30 120.0 . . ?
C30 C31 H31 119.8 . . ?
C30 C31 C32 120.3(3) . . ?
C32 C31 H31 119.8 . . ?
C27 C32 H32 119.5 . . ?
C31 C32 C27 121.0(3) . . ?
C31 C32 H32 119.5 . . ?
C34 C33 C20 122.06(19) . . ?
C34 C33 C38 117.5(2) . . ?
C38 C33 C20 120.4(2) . . ?
C33 C34 H34 119.4 . . ?
C35 C34 C33 121.2(2) . . ?
C35 C34 H34 119.4 . . ?
C34 C35 H35 119.4 . . ?
C34 C35 C36 121.2(2) . . ?
C36 C35 H35 119.4 . . ?
C35 C36 C37 117.7(2) . . ?
C35 C36 C39 121.5(2) . . ?
C37 C36 C39 120.8(2) . . ?
C36 C37 H37 119.3 . . ?
C38 C37 C36 121.3(2) . . ?
C38 C37 H37 119.3 . . ?
C33 C38 H38 119.5 . . ?
C37 C38 C33 121.0(2) . . ?
C37 C38 H38 119.5 . . ?
C40 C39 C36 121.6(3) . . ?
C44 C39 C36 120.4(3) . . ?
C44 C39 C40 118.0(3) . . ?
C39 C40 H40 119.4 . . ?
C41 C40 C39 121.1(4) . . ?
C41 C40 H40 119.4 . . ?
C40 C41 H41 120.2 . . ?
C40 C41 C42 119.6(4) . . ?
C42 C41 H41 120.2 . . ?
C41 C42 H42 119.9 . . ?
C43 C42 C41 120.2(4) . . ?
C43 C42 H42 119.9 . . ?
C42 C43 H43 120.1 . . ?
C42 C43 C44 119.7(5) . . ?
C44 C43 H43 120.1 . . ?
C39 C44 C43 121.3(4) . . ?
C39 C44 H44 119.4 . . ?
C43 C44 H44 119.4 . . ?

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
N1 C12 C20 C21 162.8(2) . . . . ?
N1 C12 C20 C33 -15.2(3) . . . . ?
N1 C13 C14 C15 -176.2(3) . . . . ?
N1 C13 C18 C17 176.3(3) . . . . ?
C1 C2 C3 C4 -1.0(4) . . . . ?
C1 C6 C7 C8 -176.9(2) . . . . ?
C1 C6 C7 C11 1.5(3) . . . . ?
C2 C1 C6 C5 1.6(3) . . . . ?
C2 C1 C6 C7 -178.7(2) . . . . ?
C2 C3 C4 C5 1.8(4) . . . . ?
C3 C4 C5 C6 -0.9(4) . . . . ?
C3 C4 C5 C10 -178.8(2) . . . . ?
C4 C5 C6 C1 -0.8(3) . . . . ?
C4 C5 C6 C7 179.5(2) . . . . ?
C4 C5 C10 C9 177.8(2) . . . . ?
C5 C6 C7 C8 2.7(3) . . . . ?
C5 C6 C7 C11 -178.81(19) . . . . ?
C6 C1 C2 C3 -0.7(4) . . . . ?
C6 C5 C10 C9 -0.2(3) . . . . ?
C6 C7 C8 C9 -0.2(3) . . . . ?
C6 C7 C8 C12 174.19(18) . . . . ?
C6 C7 C11 O1 7.5(4) . . . . ?
C6 C7 C11 N1 -175.0(2) . . . . ?
C7 C8 C9 C10 -2.5(3) . . . . ?
C7 C8 C12 N1 3.6(2) . . . . ?
C7 C8 C12 C20 -165.8(2) . . . . ?
C8 C7 C11 O1 -173.8(2) . . . . ?
C8 C7 C11 N1 3.6(2) . . . . ?
C8 C9 C10 C5 2.7(3) . . . . ?
C8 C12 C20 C21 -29.6(3) . . . . ?
C8 C12 C20 C33 152.4(2) . . . . ?
C9 C8 C12 N1 177.1(2) . . . . ?
C9 C8 C12 C20 7.7(4) . . . . ?
C10 C5 C6 C1 177.2(2) . . . . ?
C10 C5 C6 C7 -2.5(3) . . . . ?
C11 N1 C12 C8 -1.4(2) . . . . ?
C11 N1 C12 C20 168.8(2) . . . . ?
C11 N1 C13 C14 111.8(3) . . . . ?
C11 N1 C13 C18 -64.5(3) . . . . ?
C11 C7 C8 C9 -178.94(18) . . . . ?
C11 C7 C8 C12 -4.5(2) . . . . ?
C12 N1 C11 O1 176.4(2) . . . . ?
C12 N1 C11 C7 -1.3(2) . . . . ?
C12 N1 C13 C14 -41.5(3) . . . . ?
C12 N1 C13 C18 142.2(2) . . . . ?
C12 C8 C9 C10 -175.4(2) . . . . ?
C12 C20 C21 C22 -46.2(3) . . . . ?
C12 C20 C21 C26 139.4(2) . . . . ?
C12 C20 C33 C34 139.1(2) . . . . ?
C12 C20 C33 C38 -42.3(3) . . . . ?
C13 N1 C11 O1 19.8(3) . . . . ?
C13 N1 C11 C7 -157.85(19) . . . . ?
C13 N1 C12 C8 153.72(19) . . . . ?
C13 N1 C12 C20 -36.1(3) . . . . ?
C13 C14 C15 C16 0.2(5) . . . . ?
C14 C13 C18 C17 0.0(4) . . . . ?
C14 C15 C16 C17 -0.4(6) . . . . ?
C14 C15 C16 C19 177.6(4) . . . . ?
C15 C16 C17 C18 0.5(6) . . . . ?
C16 C17 C18 C13 -0.3(5) . . . . ?
C18 C13 C14 C15 0.1(4) . . . . ?
C19 C16 C17 C18 -177.5(4) . . . . ?
C20 C21 C22 C23 -174.0(2) . . . . ?
C20 C21 C26 C25 173.4(2) . . . . ?
C20 C33 C34 C35 -179.0(2) . . . . ?
C20 C33 C38 C37 178.9(2) . . . . ?
C21 C20 C33 C34 -39.0(3) . . . . ?
C21 C20 C33 C38 139.6(2) . . . . ?
C21 C22 C23 C24 1.0(3) . . . . ?
C22 C21 C26 C25 -1.2(4) . . . . ?
C22 C23 C24 C25 -2.0(3) . . . . ?
C22 C23 C24 C27 176.0(2) . . . . ?
C23 C24 C25 C26 1.5(4) . . . . ?
C23 C24 C27 C28 -30.4(3) . . . . ?
C23 C24 C27 C32 150.2(2) . . . . ?
C24 C25 C26 C21 0.2(4) . . . . ?
C24 C27 C28 C29 -179.7(2) . . . . ?
C24 C27 C32 C31 179.9(2) . . . . ?
C25 C24 C27 C28 147.6(3) . . . . ?
C25 C24 C27 C32 -31.8(3) . . . . ?
C26 C21 C22 C23 0.6(3) . . . . ?
C27 C24 C25 C26 -176.6(2) . . . . ?
C27 C28 C29 C30 0.2(4) . . . . ?
C28 C27 C32 C31 0.5(4) . . . . ?
C28 C29 C30 C31 -0.4(5) . . . . ?
C29 C30 C31 C32 0.6(5) . . . . ?
C30 C31 C32 C27 -0.6(4) . . . . ?
C32 C27 C28 C29 -0.3(4) . . . . ?
C33 C20 C21 C22 131.9(2) . . . . ?
C33 C20 C21 C26 -42.4(3) . . . . ?
C33 C34 C35 C36 0.0(4) . . . . ?
C34 C33 C38 C37 -2.5(4) . . . . ?
C34 C35 C36 C37 -2.4(4) . . . . ?
C34 C35 C36 C39 177.8(3) . . . . ?
C35 C36 C37 C38 2.3(4) . . . . ?
C35 C36 C39 C40 44.7(5) . . . . ?
C35 C36 C39 C44 -135.7(4) . . . . ?
C36 C37 C38 C33 0.1(4) . . . . ?
C36 C39 C40 C41 -178.3(4) . . . . ?
C36 C39 C44 C43 178.2(5) . . . . ?
C37 C36 C39 C40 -135.1(4) . . . . ?
C37 C36 C39 C44 44.5(5) . . . . ?
C38 C33 C34 C35 2.4(4) . . . . ?
C39 C36 C37 C38 -177.9(3) . . . . ?
C39 C40 C41 C42 0.5(8) . . . . ?
C40 C39 C44 C43 -2.2(8) . . . . ?
C40 C41 C42 C43 -3.1(9) . . . . ?
C41 C42 C43 C44 3.1(11) . . . . ?
C42 C43 C44 C39 -0.4(10) . . . . ?
C44 C39 C40 C41 2.1(7) . . . . ?

_platon_squeeze_details          
;
;
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 1.000 0.500 289 21 ' '
2 0.500 0.500 0.000 289 21 ' '

