#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/34/2223447.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2223447
loop_
_publ_author_name
'Çelik, Ísmail'
'Akkurt, Mehmet'
'Jarrahpour, Aliasghar'
'Ebrahimi, Edris'
'Büyükgüngör, Orhan'
_publ_section_title
;
 4-(9-Anthryl)-1-(3-bromophenyl)spiro[azetidine-3,9'-xanthen]-2-one
;
_journal_coeditor_code           IS2462
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2522
_journal_page_last               o2523
_journal_paper_doi               10.1107/S1600536809037830
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C35 H22 Br N O2'
_chemical_formula_moiety         'C35 H22 Br N O2'
_chemical_formula_sum            'C35 H22 Br N O2'
_chemical_formula_weight         568.44
_chemical_name_systematic
;
4-(9-Anthryl)-1-(3-bromophenyl)spiro[azetidine-3,9'-xanthen]-2-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 122.106(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1143(4)
_cell_length_b                   19.9412(5)
_cell_length_c                   14.0317(5)
_cell_measurement_reflns_used    43756
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.03
_cell_measurement_theta_min      1.71
_cell_volume                     2634.27(16)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2002)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'Stoe IPDS2'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_sigmaI/netI    0.0223
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            39287
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        26.49
_diffrn_reflns_theta_max         26.49
_diffrn_reflns_theta_min         1.99
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.594
_exptl_absorpt_correction_T_max  0.575
_exptl_absorpt_correction_T_min  0.397
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.710
_exptl_crystal_size_mid          0.590
_exptl_crystal_size_min          0.390
_refine_diff_density_max         0.518
_refine_diff_density_min         -0.739
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         5424
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0531
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0466P)²+1.4948P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1133
_refine_ls_wR_factor_ref         0.1217
_reflns_number_gt                4308
_reflns_number_total             5424
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2462.cif
_cod_data_source_block           I
_cod_original_cell_volume        2634.28(16)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2223447
_cod_database_fobs_code          2223447
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Br Br1 0.14849(5) 0.25728(2) 0.18916(4) 0.0883(2) Uani . . 1.000
O O1 0.9308(2) 0.56016(12) 0.3586(2) 0.0757(8) Uani . . 1.000
O O2 0.6106(2) 0.40529(10) 0.39082(18) 0.0675(7) Uani . . 1.000
N N1 0.4500(2) 0.47038(10) 0.23373(18) 0.0475(7) Uani . . 1.000
C C1 0.3676(3) 0.62105(14) 0.2257(2) 0.0543(8) Uani . . 1.000
C C2 0.3254(3) 0.58361(19) 0.2902(3) 0.0675(11) Uani . . 1.000
C C3 0.2423(4) 0.6108(2) 0.3248(3) 0.0878(14) Uani . . 1.000
C C4 0.1913(4) 0.6773(3) 0.2953(4) 0.1023(18) Uani . . 1.000
C C5 0.2282(4) 0.7145(2) 0.2365(4) 0.0895(16) Uani . . 1.000
C C6 0.3177(3) 0.68965(16) 0.1994(3) 0.0668(10) Uani . . 1.000
C C7 0.3553(4) 0.72966(16) 0.1396(3) 0.0732(11) Uani . . 1.000
C C8 0.4436(3) 0.70807(14) 0.1049(2) 0.0617(9) Uani . . 1.000
C C9 0.4806(4) 0.74926(15) 0.0411(3) 0.0798(13) Uani . . 1.000
C C10 0.5646(5) 0.72759(18) 0.0068(3) 0.0841(14) Uani . . 1.000
C C11 0.6241(4) 0.66303(17) 0.0374(3) 0.0724(12) Uani . . 1.000
C C12 0.5919(3) 0.62105(14) 0.0967(2) 0.0562(9) Uani . . 1.000
C C13 0.4974(3) 0.64013(13) 0.1315(2) 0.0500(8) Uani . . 1.000
C C14 0.4549(3) 0.59686(12) 0.1883(2) 0.0461(8) Uani . . 1.000
C C15 0.5078(3) 0.52549(12) 0.1999(2) 0.0429(7) Uani . . 1.000
C C16 0.6615(3) 0.50414(12) 0.3045(2) 0.0451(7) Uani . . 1.000
C C17 0.7443(3) 0.55389(13) 0.3976(2) 0.0516(8) Uani . . 1.000
C C18 0.6972(4) 0.57626(17) 0.4658(3) 0.0684(11) Uani . . 1.000
C C19 0.7729(5) 0.62392(19) 0.5495(3) 0.0836(14) Uani . . 1.000
C C20 0.8975(5) 0.64880(19) 0.5662(3) 0.0892(14) Uani . . 1.000
C C21 0.9491(4) 0.62630(17) 0.5034(3) 0.0784(11) Uani . . 1.000
C C22 0.8721(3) 0.57905(14) 0.4188(2) 0.0595(9) Uani . . 1.000
C C23 0.8774(3) 0.50458(15) 0.2907(2) 0.0584(10) Uani . . 1.000
C C24 0.9551(4) 0.4803(2) 0.2475(3) 0.0804(14) Uani . . 1.000
C C25 0.9094(4) 0.4251(2) 0.1796(3) 0.0851(16) Uani . . 1.000
C C26 0.7873(4) 0.39262(19) 0.1543(3) 0.0776(12) Uani . . 1.000
C C27 0.7097(3) 0.41707(15) 0.1974(3) 0.0610(10) Uani . . 1.000
C C28 0.7521(3) 0.47399(13) 0.2655(2) 0.0485(8) Uani . . 1.000
C C29 0.5791(3) 0.45045(13) 0.3248(2) 0.0498(8) Uani . . 1.000
C C30 0.3212(3) 0.43540(13) 0.1680(2) 0.0460(8) Uani . . 1.000
C C31 0.3017(3) 0.37439(13) 0.2052(2) 0.0500(8) Uani . . 1.000
C C32 0.1775(3) 0.33946(14) 0.1364(3) 0.0561(10) Uani . . 1.000
C C33 0.0742(3) 0.36319(18) 0.0326(3) 0.0667(11) Uani . . 1.000
C C34 0.0942(3) 0.42442(19) -0.0021(3) 0.0703(11) Uani . . 1.000
C C35 0.2170(3) 0.46130(16) 0.0651(2) 0.0601(10) Uani . . 1.000
H H2 0.35540 0.53940 0.30900 0.0810 Uiso calc R 1.000
H H3 0.21890 0.58540 0.36830 0.1050 Uiso calc R 1.000
H H4 0.13200 0.69490 0.31710 0.1230 Uiso calc R 1.000
H H5 0.19490 0.75840 0.21870 0.1070 Uiso calc R 1.000
H H7 0.31960 0.77310 0.12190 0.0880 Uiso calc R 1.000
H H9 0.44480 0.79270 0.02290 0.0950 Uiso calc R 1.000
H H10 0.58390 0.75500 -0.03710 0.1010 Uiso calc R 1.000
H H11 0.68670 0.64890 0.01650 0.0870 Uiso calc R 1.000
H H12 0.63270 0.57860 0.11530 0.0670 Uiso calc R 1.000
H H15 0.50170 0.51280 0.13010 0.0520 Uiso calc R 1.000
H H18 0.61330 0.55910 0.45540 0.0820 Uiso calc R 1.000
H H19 0.73900 0.63880 0.59370 0.1000 Uiso calc R 1.000
H H20 0.94720 0.68130 0.62100 0.1070 Uiso calc R 1.000
H H21 1.03530 0.64230 0.51670 0.0940 Uiso calc R 1.000
H H24 1.03880 0.50150 0.26460 0.0960 Uiso calc R 1.000
H H25 0.96180 0.40930 0.15020 0.1020 Uiso calc R 1.000
H H26 0.75710 0.35470 0.10880 0.0930 Uiso calc R 1.000
H H27 0.62690 0.39500 0.18060 0.0730 Uiso calc R 1.000
H H31 0.37060 0.35740 0.27510 0.0600 Uiso calc R 1.000
H H33 -0.00770 0.33840 -0.01330 0.0800 Uiso calc R 1.000
H H34 0.02440 0.44130 -0.07170 0.0850 Uiso calc R 1.000
H H35 0.22910 0.50290 0.04130 0.0720 Uiso calc R 1.000
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
Br Br -0.2901 2.4595 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 -23 -24 0.1714
4 23 28 0.1735
-15 -24 14 0.2780
-27 9 2 0.2930
6 9 -7 0.2737
9 -29 1 0.4154
-8 9 -5 0.3571
10 28 -17 0.3133
17 -4 -30 0.2429
10 -29 -6 0.3760
-30 5 29 0.4241
0 -17 13 0.3848
12 7 -25 0.2919
-1 30 8 0.3699
3 -28 -26 0.1909
-4 -4 21 0.2322
9 7 13 0.2603
-9 -14 23 0.2698
-3 -6 -10 0.2236
-3 -26 -5 0.3311
9 24 -11 0.3240
-15 1 1 0.2981
25 8 5 0.3774
-4 -2 1 0.2958
-8 -22 9 0.3450
-13 28 7 0.3560
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C22 O1 C23 . . . 118.6(3) no
C15 N1 C29 . . . 95.5(2) no
C15 N1 C30 . . . 128.6(2) no
C29 N1 C30 . . . 131.2(2) no
C2 C1 C6 . . . 116.4(3) no
C2 C1 C14 . . . 125.3(3) no
C6 C1 C14 . . . 118.3(3) no
C1 C2 C3 . . . 122.0(3) no
C2 C3 C4 . . . 120.7(4) no
C3 C4 C5 . . . 119.9(5) no
C4 C5 C6 . . . 122.4(4) no
C1 C6 C5 . . . 118.7(3) no
C1 C6 C7 . . . 120.3(3) no
C5 C6 C7 . . . 121.1(3) no
C6 C7 C8 . . . 122.7(3) no
C7 C8 C9 . . . 122.6(3) no
C7 C8 C13 . . . 118.4(3) no
C9 C8 C13 . . . 118.9(3) no
C8 C9 C10 . . . 122.1(3) no
C9 C10 C11 . . . 119.6(4) no
C10 C11 C12 . . . 121.2(4) no
C11 C12 C13 . . . 121.9(3) no
C8 C13 C12 . . . 116.1(3) no
C8 C13 C14 . . . 120.0(3) no
C12 C13 C14 . . . 123.9(3) no
C1 C14 C13 . . . 120.2(2) no
C1 C14 C15 . . . 125.8(3) no
C13 C14 C15 . . . 114.0(3) no
N1 C15 C14 . . . 121.6(3) no
N1 C15 C16 . . . 86.68(19) no
C14 C15 C16 . . . 120.7(2) no
C15 C16 C17 . . . 118.7(2) no
C15 C16 C28 . . . 111.4(2) no
C15 C16 C29 . . . 84.5(2) no
C17 C16 C28 . . . 111.2(3) no
C17 C16 C29 . . . 116.8(2) no
C28 C16 C29 . . . 111.8(2) no
C16 C17 C18 . . . 122.1(3) no
C16 C17 C22 . . . 120.8(3) no
C18 C17 C22 . . . 117.2(3) no
C17 C18 C19 . . . 121.4(4) no
C18 C19 C20 . . . 119.6(5) no
C19 C20 C21 . . . 120.5(4) no
C20 C21 C22 . . . 119.7(4) no
O1 C22 C17 . . . 122.7(2) no
O1 C22 C21 . . . 115.7(3) no
C17 C22 C21 . . . 121.6(3) no
O1 C23 C24 . . . 116.6(3) no
O1 C23 C28 . . . 122.6(3) no
C24 C23 C28 . . . 120.9(3) no
C23 C24 C25 . . . 120.1(4) no
C24 C25 C26 . . . 120.8(4) no
C25 C26 C27 . . . 118.9(3) no
C26 C27 C28 . . . 121.7(4) no
C16 C28 C23 . . . 120.6(2) no
C16 C28 C27 . . . 121.8(3) no
C23 C28 C27 . . . 117.5(3) no
O2 C29 N1 . . . 131.5(3) no
O2 C29 C16 . . . 135.1(3) no
N1 C29 C16 . . . 93.3(2) no
N1 C30 C31 . . . 119.8(2) no
N1 C30 C35 . . . 119.6(3) no
C31 C30 C35 . . . 120.6(3) no
C30 C31 C32 . . . 118.6(3) no
Br1 C32 C31 . . . 118.5(2) no
Br1 C32 C33 . . . 119.5(3) no
C31 C32 C33 . . . 122.0(3) no
C32 C33 C34 . . . 118.7(3) no
C33 C34 C35 . . . 121.0(3) no
C30 C35 C34 . . . 119.1(3) no
C1 C2 H2 . . . 119.00 no
C3 C2 H2 . . . 119.00 no
C2 C3 H3 . . . 120.00 no
C4 C3 H3 . . . 120.00 no
C3 C4 H4 . . . 120.00 no
C5 C4 H4 . . . 120.00 no
C4 C5 H5 . . . 119.00 no
C6 C5 H5 . . . 119.00 no
C6 C7 H7 . . . 119.00 no
C8 C7 H7 . . . 119.00 no
C8 C9 H9 . . . 119.00 no
C10 C9 H9 . . . 119.00 no
C9 C10 H10 . . . 120.00 no
C11 C10 H10 . . . 120.00 no
C10 C11 H11 . . . 119.00 no
C12 C11 H11 . . . 119.00 no
C11 C12 H12 . . . 119.00 no
C13 C12 H12 . . . 119.00 no
N1 C15 H15 . . . 109.00 no
C14 C15 H15 . . . 109.00 no
C16 C15 H15 . . . 109.00 no
C17 C18 H18 . . . 119.00 no
C19 C18 H18 . . . 119.00 no
C18 C19 H19 . . . 120.00 no
C20 C19 H19 . . . 120.00 no
C19 C20 H20 . . . 120.00 no
C21 C20 H20 . . . 120.00 no
C20 C21 H21 . . . 120.00 no
C22 C21 H21 . . . 120.00 no
C23 C24 H24 . . . 120.00 no
C25 C24 H24 . . . 120.00 no
C24 C25 H25 . . . 120.00 no
C26 C25 H25 . . . 120.00 no
C25 C26 H26 . . . 121.00 no
C27 C26 H26 . . . 120.00 no
C26 C27 H27 . . . 119.00 no
C28 C27 H27 . . . 119.00 no
C30 C31 H31 . . . 121.00 no
C32 C31 H31 . . . 121.00 no
C32 C33 H33 . . . 121.00 no
C34 C33 H33 . . . 121.00 no
C33 C34 H34 . . . 119.00 no
C35 C34 H34 . . . 120.00 no
C30 C35 H35 . . . 120.00 no
C34 C35 H35 . . . 120.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C32 . . 1.895(3) no
O1 C22 . . 1.366(4) no
O1 C23 . . 1.374(4) no
O2 C29 . . 1.203(3) no
N1 C15 . . 1.473(4) no
N1 C29 . . 1.379(4) no
N1 C30 . . 1.408(4) no
C1 C2 . . 1.431(5) no
C1 C6 . . 1.448(4) no
C1 C14 . . 1.411(5) no
C2 C3 . . 1.364(6) no
C3 C4 . . 1.415(7) no
C4 C5 . . 1.326(7) no
C5 C6 . . 1.434(6) no
C6 C7 . . 1.374(5) no
C7 C8 . . 1.376(6) no
C8 C9 . . 1.427(5) no
C8 C13 . . 1.448(4) no
C9 C10 . . 1.330(7) no
C10 C11 . . 1.406(5) no
C11 C12 . . 1.356(5) no
C12 C13 . . 1.425(5) no
C13 C14 . . 1.415(4) no
C14 C15 . . 1.515(4) no
C15 C16 . . 1.609(4) no
C16 C17 . . 1.503(3) no
C16 C28 . . 1.504(5) no
C16 C29 . . 1.531(4) no
C17 C18 . . 1.386(5) no
C17 C22 . . 1.382(5) no
C18 C19 . . 1.393(5) no
C19 C20 . . 1.369(8) no
C20 C21 . . 1.358(7) no
C21 C22 . . 1.396(4) no
C23 C24 . . 1.380(6) no
C23 C28 . . 1.383(5) no
C24 C25 . . 1.365(5) no
C25 C26 . . 1.369(7) no
C26 C27 . . 1.379(6) no
C27 C28 . . 1.395(4) no
C30 C31 . . 1.386(4) no
C30 C35 . . 1.384(4) no
C31 C32 . . 1.381(5) no
C32 C33 . . 1.373(5) no
C33 C34 . . 1.376(5) no
C34 C35 . . 1.387(5) no
C2 H2 . . 0.9300 no
C3 H3 . . 0.9300 no
C4 H4 . . 0.9300 no
C5 H5 . . 0.9300 no
C7 H7 . . 0.9300 no
C9 H9 . . 0.9300 no
C10 H10 . . 0.9300 no
C11 H11 . . 0.9300 no
C12 H12 . . 0.9300 no
C15 H15 . . 0.9800 no
C18 H18 . . 0.9300 no
C19 H19 . . 0.9300 no
C20 H20 . . 0.9300 no
C21 H21 . . 0.9300 no
C24 H24 . . 0.9300 no
C25 H25 . . 0.9300 no
C26 H26 . . 0.9300 no
C27 H27 . . 0.9300 no
C31 H31 . . 0.9300 no
C33 H33 . . 0.9300 no
C34 H34 . . 0.9300 no
C35 H35 . . 0.9300 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Br1 C21 3.491(4) . 2_645 no
O2 C31 3.073(4) . . no
O2 H31 2.4600 . . no
O2 H7 2.7800 . 2_645 no
O2 H9 2.7700 . 2_645 no
O2 H3 2.8700 . 3_666 no
N1 C2 2.968(4) . . no
N1 C27 3.359(5) . . no
N1 H2 2.3000 . . no
N1 H27 2.8700 . . no
C1 C18 3.528(5) . . no
C2 N1 2.968(4) . . no
C2 C18 3.514(6) . . no
C2 C30 3.405(5) . . no
C4 C9 3.548(6) . 4_565 no
C9 C4 3.548(6) . 4_564 no
C12 C16 3.484(4) . . no
C12 C28 3.591(4) . . no
C14 C35 3.525(4) . . no
C14 C18 3.382(4) . . no
C16 C12 3.484(4) . . no
C18 C14 3.382(4) . . no
C18 C2 3.514(6) . . no
C18 C1 3.528(5) . . no
C19 C24 3.524(6) . 3_766 no
C20 C25 3.371(5) . 3_766 no
C20 C24 3.405(5) . 3_766 no
C21 C23 3.599(4) . 3_766 no
C21 Br1 3.491(4) . 2_655 no
C23 C21 3.599(4) . 3_766 no
C24 C20 3.405(5) . 3_766 no
C24 C19 3.524(6) . 3_766 no
C25 C20 3.371(5) . 3_766 no
C27 N1 3.359(5) . . no
C28 C12 3.591(4) . . no
C30 C2 3.405(5) . . no
C31 O2 3.073(4) . . no
C35 C14 3.525(4) . . no
C2 H18 2.8200 . . no
C3 H24 2.9200 . 1_455 no
C4 H9 2.9900 . 4_565 no
C5 H33 2.9600 . 3_565 no
C6 H33 3.0700 . 3_565 no
C8 H26 2.9000 . 3_665 no
C9 H31 3.0800 . 2_655 no
C11 H27 3.0700 . 3_665 no
C12 H15 2.5300 . . no
C13 H26 3.0400 . 3_665 no
C14 H35 2.9300 . . no
C15 H12 2.4900 . . no
C15 H27 3.0000 . . no
C15 H2 2.8400 . . no
C15 H35 2.7200 . . no
C16 H12 2.9100 . . no
C19 H10 3.0000 . 4_565 no
C23 H12 2.9200 . . no
C24 H34 3.0300 . 3_665 no
C25 H35 2.9900 . 3_665 no
C27 H15 2.7500 . . no
C28 H12 2.7500 . . no
C29 H27 2.6000 . . no
C29 H18 2.7300 . . no
C29 H31 2.7500 . . no
C29 H2 2.9600 . . no
C30 H2 2.7500 . . no
C30 H11 3.0500 . 3_665 no
C31 H19 3.1000 . 3_666 no
C32 H25 2.8700 . 1_455 no
C33 H11 3.0900 . 3_665 no
C33 H25 2.7100 . 1_455 no
C34 H11 2.9400 . 3_665 no
C35 H15 2.9700 . . no
C35 H11 2.9300 . 3_665 no
H2 N1 2.3000 . . no
H2 C15 2.8400 . . no
H2 C29 2.9600 . . no
H2 C30 2.7500 . . no
H2 H18 2.5200 . . no
H3 H24 2.4100 . 1_455 no
H3 O2 2.8700 . 3_666 no
H5 H7 2.4200 . . no
H7 H5 2.4200 . . no
H7 H9 2.4600 . . no
H7 O2 2.7800 . 2_655 no
H9 H7 2.4600 . . no
H9 O2 2.7700 . 2_655 no
H9 C4 2.9900 . 4_564 no
H10 C19 3.0000 . 4_564 no
H11 C30 3.0500 . 3_665 no
H11 C33 3.0900 . 3_665 no
H11 C34 2.9400 . 3_665 no
H11 C35 2.9300 . 3_665 no
H12 C15 2.4900 . . no
H12 C16 2.9100 . . no
H12 C23 2.9200 . . no
H12 C28 2.7500 . . no
H12 H15 2.0500 . . no
H15 C12 2.5300 . . no
H15 C27 2.7500 . . no
H15 C35 2.9700 . . no
H15 H12 2.0500 . . no
H15 H35 2.6000 . . no
H18 C2 2.8200 . . no
H18 C29 2.7300 . . no
H18 H2 2.5200 . . no
H19 C31 3.1000 . 3_666 no
H24 C3 2.9200 . 1_655 no
H24 H3 2.4100 . 1_655 no
H25 C32 2.8700 . 1_655 no
H25 C33 2.7100 . 1_655 no
H26 C8 2.9000 . 3_665 no
H26 C13 3.0400 . 3_665 no
H27 N1 2.8700 . . no
H27 C15 3.0000 . . no
H27 C29 2.6000 . . no
H27 C11 3.0700 . 3_665 no
H31 O2 2.4600 . . no
H31 C29 2.7500 . . no
H31 C9 3.0800 . 2_645 no
H33 C5 2.9600 . 3_565 no
H33 C6 3.0700 . 3_565 no
H34 C24 3.0300 . 3_665 no
H35 C14 2.9300 . . no
H35 C15 2.7200 . . no
H35 H15 2.6000 . . no
H35 C25 2.9900 . 3_665 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C2 H2 N1 . 0.93 2.30 2.968(4) 128 yes
C31 H31 O2 . 0.93 2.46 3.073(4) 123 yes
C11 H11 Cg2 3_665 0.93 2.75 3.653(5) 164 yes
C26 H26 Cg1 3_665 0.93 2.96 3.616(4) 129 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C23 O1 C22 C21 . . . . 166.8(3) no
C22 O1 C23 C24 . . . . -168.8(3) no
C22 O1 C23 C28 . . . . 11.5(4) no
C23 O1 C22 C17 . . . . -13.8(4) no
C29 N1 C30 C31 . . . . 13.3(5) no
C29 N1 C30 C35 . . . . -164.7(3) no
C29 N1 C15 C16 . . . . 0.4(2) no
C15 N1 C30 C35 . . . . -14.9(5) no
C30 N1 C15 C14 . . . . 78.4(3) no
C15 N1 C29 C16 . . . . -0.4(2) no
C30 N1 C15 C16 . . . . -157.3(3) no
C29 N1 C15 C14 . . . . -123.9(2) no
C30 N1 C29 C16 . . . . 156.3(3) no
C15 N1 C30 C31 . . . . 163.1(3) no
C15 N1 C29 O2 . . . . -177.8(3) no
C30 N1 C29 O2 . . . . -21.1(5) no
C2 C1 C14 C13 . . . . -175.7(3) no
C2 C1 C6 C7 . . . . 178.8(3) no
C6 C1 C14 C15 . . . . -175.1(3) no
C14 C1 C6 C5 . . . . 179.6(3) no
C2 C1 C6 C5 . . . . -1.5(5) no
C14 C1 C6 C7 . . . . -0.1(5) no
C14 C1 C2 C3 . . . . 179.0(3) no
C6 C1 C14 C13 . . . . 3.1(4) no
C6 C1 C2 C3 . . . . 0.2(5) no
C2 C1 C14 C15 . . . . 6.2(5) no
C1 C2 C3 C4 . . . . 1.6(6) no
C2 C3 C4 C5 . . . . -2.2(7) no
C3 C4 C5 C6 . . . . 0.9(7) no
C4 C5 C6 C1 . . . . 1.0(6) no
C4 C5 C6 C7 . . . . -179.3(4) no
C1 C6 C7 C8 . . . . -1.9(5) no
C5 C6 C7 C8 . . . . 178.4(4) no
C6 C7 C8 C13 . . . . 0.8(5) no
C6 C7 C8 C9 . . . . 178.9(3) no
C7 C8 C13 C14 . . . . 2.3(4) no
C7 C8 C9 C10 . . . . -179.1(4) no
C13 C8 C9 C10 . . . . -1.1(5) no
C9 C8 C13 C12 . . . . 3.7(4) no
C7 C8 C13 C12 . . . . -178.1(3) no
C9 C8 C13 C14 . . . . -175.9(3) no
C8 C9 C10 C11 . . . . -2.5(6) no
C9 C10 C11 C12 . . . . 3.3(6) no
C10 C11 C12 C13 . . . . -0.4(5) no
C11 C12 C13 C8 . . . . -3.1(4) no
C11 C12 C13 C14 . . . . 176.6(3) no
C12 C13 C14 C15 . . . . -5.5(4) no
C8 C13 C14 C15 . . . . 174.2(2) no
C12 C13 C14 C1 . . . . 176.2(3) no
C8 C13 C14 C1 . . . . -4.2(4) no
C1 C14 C15 N1 . . . . 11.7(4) no
C1 C14 C15 C16 . . . . -94.9(4) no
C13 C14 C15 C16 . . . . 86.9(3) no
C13 C14 C15 N1 . . . . -166.5(2) no
N1 C15 C16 C29 . . . . -0.37(19) no
C14 C15 C16 C17 . . . . 7.2(4) no
N1 C15 C16 C17 . . . . -118.0(3) no
N1 C15 C16 C28 . . . . 110.9(2) no
C14 C15 C16 C29 . . . . 124.8(3) no
C14 C15 C16 C28 . . . . -123.9(3) no
C29 C16 C28 C27 . . . . 33.9(3) no
C29 C16 C28 C23 . . . . -150.1(2) no
C15 C16 C28 C27 . . . . -58.7(3) no
C15 C16 C29 O2 . . . . 177.7(4) no
C15 C16 C28 C23 . . . . 117.3(3) no
C28 C16 C17 C18 . . . . -164.1(3) no
C28 C16 C17 C22 . . . . 15.6(3) no
C29 C16 C17 C18 . . . . -34.3(4) no
C29 C16 C17 C22 . . . . 145.5(3) no
C15 C16 C17 C18 . . . . 64.6(4) no
C17 C16 C28 C23 . . . . -17.7(3) no
C17 C16 C28 C27 . . . . 166.4(3) no
C15 C16 C29 N1 . . . . 0.4(2) no
C15 C16 C17 C22 . . . . -115.6(3) no
C28 C16 C29 N1 . . . . -110.5(2) no
C28 C16 C29 O2 . . . . 66.7(4) no
C17 C16 C29 O2 . . . . -62.8(5) no
C17 C16 C29 N1 . . . . 119.9(3) no
C16 C17 C22 C21 . . . . 178.7(3) no
C22 C17 C18 C19 . . . . 2.3(5) no
C18 C17 C22 O1 . . . . 179.0(3) no
C16 C17 C18 C19 . . . . -178.0(3) no
C18 C17 C22 C21 . . . . -1.6(4) no
C16 C17 C22 O1 . . . . -0.7(4) no
C17 C18 C19 C20 . . . . -0.8(5) no
C18 C19 C20 C21 . . . . -1.4(6) no
C19 C20 C21 C22 . . . . 2.1(5) no
C20 C21 C22 C17 . . . . -0.6(5) no
C20 C21 C22 O1 . . . . 178.9(3) no
O1 C23 C24 C25 . . . . 179.8(3) no
C28 C23 C24 C25 . . . . -0.5(5) no
O1 C23 C28 C16 . . . . 5.1(4) no
C24 C23 C28 C16 . . . . -174.6(3) no
C24 C23 C28 C27 . . . . 1.5(4) no
O1 C23 C28 C27 . . . . -178.8(3) no
C23 C24 C25 C26 . . . . -0.7(6) no
C24 C25 C26 C27 . . . . 0.8(6) no
C25 C26 C27 C28 . . . . 0.3(5) no
C26 C27 C28 C16 . . . . 174.7(3) no
C26 C27 C28 C23 . . . . -1.4(5) no
N1 C30 C31 C32 . . . . -176.6(3) no
C35 C30 C31 C32 . . . . 1.3(5) no
N1 C30 C35 C34 . . . . 176.0(3) no
C31 C30 C35 C34 . . . . -1.9(5) no
C30 C31 C32 Br1 . . . . -178.2(3) no
C30 C31 C32 C33 . . . . 0.5(5) no
Br1 C32 C33 C34 . . . . 177.0(3) no
C31 C32 C33 C34 . . . . -1.7(6) no
C32 C33 C34 C35 . . . . 1.1(6) no
C33 C34 C35 C30 . . . . 0.7(5) no
