#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/46/1504644.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1504644
loop_
_publ_author_name
'Shi, Yubai'
'Qian, Hualei'
'Li, Yan'
'Yue, Wan'
'Wang, Zhaohui'
_publ_section_title
;
 Copper-mediated domino process for the synthesis of tetraiodinated
 di(perylene bisimide).
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              2337
_journal_page_last               2340
_journal_paper_doi               10.1021/ol800482y
_journal_volume                  10
_journal_year                    2008
_chemical_formula_moiety         'C108 H98 I4 N4 O8'
_chemical_formula_sum            'C108 H98 I4 N4 O8'
_chemical_formula_weight         2087.50
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 120.923(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   35.341(5)
_cell_length_b                   14.3173(14)
_cell_length_c                   29.323(3)
_cell_measurement_reflns_used    11334
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      1.6
_cell_volume                     12728(3)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalClear
_computing_publication_material  'CrystalStructure 3.7.0'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_sigmaI/netI    0.0462
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            46815
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.60
_exptl_absorpt_coefficient_mu    1.023
_exptl_absorpt_correction_T_max  0.9046
_exptl_absorpt_correction_T_min  0.7913
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.089
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             4200
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_platon_squeeze_details
;
;
_refine_diff_density_max         1.968
_refine_diff_density_min         -3.071
_refine_diff_density_rms         0.114
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     567
_refine_ls_number_reflns         11193
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.1139
_refine_ls_R_factor_gt           0.0951
_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)+(0.0800P)²+145.4738P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2257
_refine_ls_wR_factor_ref         0.2385
_reflns_number_gt                8518
_reflns_number_total             11193
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol800482y-file001.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        12729(3)
_cod_database_code               1504644
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
I1 I 0.42828(2) 0.42147(8) 0.42867(3) 0.1220(4) Uani 1 1 d .
I2 I 0.42371(2) 0.67502(8) 0.43088(2) 0.1276(5) Uani 1 1 d .
O1 O 0.27153(18) 0.3749(5) 0.2397(2) 0.0746(19) Uani 1 1 d .
O2 O 0.28357(16) 0.4720(3) 0.10060(19) 0.0437(11) Uani 1 1 d .
O3 O 0.59908(18) 0.7444(4) 0.51001(18) 0.0538(13) Uani 1 1 d .
O4 O 0.63566(15) 0.6898(3) 0.38537(17) 0.0411(11) Uani 1 1 d .
N1 N 0.27535(19) 0.4373(4) 0.1713(2) 0.0448(14) Uani 1 1 d .
N2 N 0.61887(19) 0.7077(4) 0.4493(2) 0.0397(13) Uani 1 1 d .
C1 C 0.2928(3) 0.4182(6) 0.2251(3) 0.054(2) Uani 1 1 d .
C2 C 0.3374(2) 0.4556(6) 0.2618(3) 0.0484(18) Uani 1 1 d .
C3 C 0.3565(3) 0.4408(7) 0.3158(3) 0.067(3) Uani 1 1 d .
H3A H 0.3410 0.4065 0.3288 0.080 Uiso 1 1 calc R
C4 C 0.3980(3) 0.4757(7) 0.3510(3) 0.068(3) Uani 1 1 d .
C5 C 0.4208(2) 0.5315(6) 0.3336(3) 0.053(2) Uani 1 1 d .
C6 C 0.4615(2) 0.5844(6) 0.3675(3) 0.0485(19) Uani 1 1 d .
C7 C 0.4714(3) 0.6343(7) 0.4128(3) 0.065(2) Uani 1 1 d .
C8 C 0.5131(3) 0.6745(6) 0.4445(3) 0.058(2) Uani 1 1 d .
H8A H 0.5194 0.7066 0.4760 0.069 Uiso 1 1 calc R
C9 C 0.5454(2) 0.6686(5) 0.4313(3) 0.0415(16) Uani 1 1 d .
C10 C 0.5892(3) 0.7101(5) 0.4678(3) 0.0454(17) Uani 1 1 d .
C11 C 0.6095(2) 0.6746(5) 0.3997(2) 0.0378(15) Uani 1 1 d .
C12 C 0.5666(2) 0.6252(4) 0.3657(2) 0.0352(14) Uani 1 1 d .
C13 C 0.5350(2) 0.6274(5) 0.3823(2) 0.0384(15) Uani 1 1 d .
C14 C 0.4924(2) 0.5922(5) 0.3495(3) 0.0415(16) Uani 1 1 d .
C15 C 0.4780(2) 0.5759(4) 0.2956(2) 0.0338(14) Uani 1 1 d .
C16 C 0.4321(2) 0.5596(5) 0.2578(3) 0.0367(15) Uani 1 1 d .
C17 C 0.4045(2) 0.5322(5) 0.2781(3) 0.0423(16) Uani 1 1 d .
C18 C 0.3620(2) 0.4973(5) 0.2423(3) 0.0415(16) Uani 1 1 d .
C19 C 0.3456(2) 0.5000(4) 0.1868(3) 0.0355(14) Uani 1 1 d .
C20 C 0.2997(2) 0.4693(5) 0.1483(3) 0.0391(15) Uani 1 1 d .
C21 C 0.3717(2) 0.5317(4) 0.1676(3) 0.0351(14) Uani 1 1 d .
H21A H 0.3603 0.5327 0.1304 0.042 Uiso 1 1 calc R
C22 C 0.4152(2) 0.5624(4) 0.2026(2) 0.0304(13) Uani 1 1 d .
C23 C 0.5084(2) 0.5780(4) 0.2780(2) 0.0345(14) Uani 1 1 d .
C24 C 0.5544(2) 0.5890(4) 0.3157(2) 0.0312(13) Uani 1 1 d .
C25 C 0.2289(3) 0.4160(6) 0.1347(3) 0.0506(19) Uani 1 1 d .
C26 C 0.1970(2) 0.4817(6) 0.1275(3) 0.0499(18) Uani 1 1 d .
C27 C 0.1534(3) 0.4588(7) 0.0931(3) 0.063(2) Uani 1 1 d .
H27A H 0.1310 0.5015 0.0882 0.076 Uiso 1 1 calc R
C28 C 0.1413(3) 0.3751(7) 0.0655(3) 0.071(3) Uani 1 1 d .
H28A H 0.1111 0.3619 0.0413 0.085 Uiso 1 1 calc R
C29 C 0.1731(3) 0.3111(7) 0.0731(3) 0.070(3) Uani 1 1 d .
H29A H 0.1646 0.2536 0.0543 0.084 Uiso 1 1 calc R
C30 C 0.2177(3) 0.3299(6) 0.1082(3) 0.060(2) Uani 1 1 d .
C31 C 0.2096(2) 0.5740(6) 0.1568(3) 0.0532(19) Uani 1 1 d .
H31A H 0.2408 0.5876 0.1676 0.064 Uiso 1 1 calc R
C32 C 0.1812(3) 0.6558(6) 0.1228(4) 0.069(2) Uani 1 1 d .
H32A H 0.1948 0.7148 0.1408 0.103 Uiso 1 1 calc R
H32B H 0.1517 0.6509 0.1178 0.103 Uiso 1 1 calc R
H32C H 0.1791 0.6542 0.0882 0.103 Uiso 1 1 calc R
C33 C 0.2073(4) 0.5694(7) 0.2061(4) 0.085(3) Uani 1 1 d .
H33A H 0.2181 0.6282 0.2257 0.128 Uiso 1 1 calc R
H33B H 0.2256 0.5177 0.2284 0.128 Uiso 1 1 calc R
H33C H 0.1767 0.5594 0.1966 0.128 Uiso 1 1 calc R
C34 C 0.2520(4) 0.2585(6) 0.1155(4) 0.077(3) Uani 1 1 d .
H34A H 0.2814 0.2846 0.1423 0.092 Uiso 1 1 calc R
C35 C 0.2531(5) 0.2406(8) 0.0643(5) 0.100(4) Uani 1 1 d .
H35A H 0.2537 0.3004 0.0485 0.151 Uiso 1 1 calc R
H35B H 0.2267 0.2055 0.0390 0.151 Uiso 1 1 calc R
H35C H 0.2795 0.2044 0.0730 0.151 Uiso 1 1 calc R
C36 C 0.2461(5) 0.1660(7) 0.1392(5) 0.101(4) Uani 1 1 d .
H36A H 0.2490 0.1789 0.1736 0.151 Uiso 1 1 calc R
H36B H 0.2688 0.1212 0.1439 0.151 Uiso 1 1 calc R
H36C H 0.2169 0.1398 0.1149 0.151 Uiso 1 1 calc R
C37 C 0.6626(2) 0.7472(5) 0.4843(2) 0.0421(16) Uani 1 1 d .
C38 C 0.6942(2) 0.6898(5) 0.5247(3) 0.0448(16) Uani 1 1 d .
C39 C 0.7360(3) 0.7260(5) 0.5569(3) 0.0485(17) Uani 1 1 d .
H39A H 0.7586 0.6878 0.5834 0.058 Uiso 1 1 calc R
C40 C 0.7450(3) 0.8176(5) 0.5510(3) 0.0527(19) Uani 1 1 d .
H40A H 0.7739 0.8416 0.5738 0.063 Uiso 1 1 calc R
C41 C 0.7130(3) 0.8753(6) 0.5124(3) 0.056(2) Uani 1 1 d .
H41A H 0.7196 0.9388 0.5100 0.067 Uiso 1 1 calc R
C42 C 0.6710(3) 0.8399(5) 0.4773(3) 0.0469(18) Uani 1 1 d .
C43 C 0.6839(3) 0.5888(5) 0.5334(3) 0.0455(17) Uani 1 1 d .
H43A H 0.6517 0.5774 0.5084 0.055 Uiso 1 1 calc R
C44 C 0.7094(3) 0.5174(5) 0.5211(4) 0.067(2) Uani 1 1 d .
H44A H 0.7030 0.4544 0.5285 0.101 Uiso 1 1 calc R
H44B H 0.7411 0.5298 0.5434 0.101 Uiso 1 1 calc R
H44C H 0.7005 0.5220 0.4836 0.101 Uiso 1 1 calc R
C45 C 0.6931(3) 0.5776(5) 0.5902(3) 0.0496(18) Uani 1 1 d .
H45A H 0.6780 0.6274 0.5977 0.074 Uiso 1 1 calc R
H45B H 0.7249 0.5814 0.6154 0.074 Uiso 1 1 calc R
H45C H 0.6821 0.5167 0.5937 0.074 Uiso 1 1 calc R
C46 C 0.6356(3) 0.9006(5) 0.4337(3) 0.056(2) Uani 1 1 d .
H46A H 0.6110 0.8594 0.4078 0.068 Uiso 1 1 calc R
C47 C 0.6174(5) 0.9681(8) 0.4588(5) 0.126(6) Uani 1 1 d .
H47A H 0.6041 0.9322 0.4754 0.189 Uiso 1 1 calc R
H47B H 0.5951 1.0087 0.4311 0.189 Uiso 1 1 calc R
H47C H 0.6415 1.0064 0.4857 0.189 Uiso 1 1 calc R
C48 C 0.6525(4) 0.9572(7) 0.4036(4) 0.086(3) Uani 1 1 d .
H48A H 0.6281 0.9924 0.3750 0.130 Uiso 1 1 calc R
H48B H 0.6649 0.9147 0.3884 0.130 Uiso 1 1 calc R
H48C H 0.6754 1.0006 0.4281 0.130 Uiso 1 1 calc R
C49 C 0.5628(4) 0.2176(6) 0.3915(4) 0.094(4) Uani 1 1 d D
H49A H 0.5458 0.2335 0.3532 0.113 Uiso 1 1 calc R
H49B H 0.5586 0.1501 0.3950 0.113 Uiso 1 1 calc R
C50 C 0.6115(4) 0.2372(7) 0.4135(4) 0.095(3) Uani 1 1 d D
H50A H 0.6215 0.2018 0.3926 0.114 Uiso 1 1 calc R
H50B H 0.6287 0.2152 0.4508 0.114 Uiso 1 1 calc R
C51 C 0.6206(4) 0.3409(7) 0.4117(4) 0.091(3) Uani 1 1 d D
H51A H 0.6065 0.3622 0.3743 0.109 Uiso 1 1 calc R
H51B H 0.6527 0.3520 0.4292 0.109 Uiso 1 1 calc R
C52 C 0.6016(3) 0.3946(6) 0.4406(4) 0.087(3) Uani 1 1 d D
H52A H 0.6181 0.3768 0.4787 0.104 Uiso 1 1 calc R
H52B H 0.6062 0.4623 0.4384 0.104 Uiso 1 1 calc R
C53 C 0.5527(3) 0.3770(6) 0.4183(4) 0.083(3) Uani 1 1 d D
H53A H 0.5354 0.4000 0.3813 0.100 Uiso 1 1 calc R
H53B H 0.5427 0.4108 0.4398 0.100 Uiso 1 1 calc R
C54 C 0.5454(4) 0.2725(6) 0.4198(4) 0.090(3) Uani 1 1 d D
H54A H 0.5602 0.2517 0.4573 0.108 Uiso 1 1 calc R
H54B H 0.5134 0.2602 0.4034 0.108 Uiso 1 1 calc R
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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_3
C1 N1 C20 125.4(6) .
C1 N1 C25 118.0(5) .
C20 N1 C25 116.4(6) .
C11 N2 C10 125.8(6) .
C11 N2 C37 117.6(5) .
C10 N2 C37 116.6(5) .
O1 C1 N1 120.4(8) .
O1 C1 C2 123.5(7) .
N1 C1 C2 116.1(6) .
C3 C2 C18 119.6(7) .
C3 C2 C1 119.2(6) .
C18 C2 C1 120.8(6) .
C2 C3 C4 120.3(7) .
C2 C3 H3A 119.8 .
C4 C3 H3A 119.8 .
C3 C4 C5 121.4(7) .
C3 C4 I1 115.4(6) .
C5 C4 I1 122.4(6) .
C4 C5 C17 116.7(8) .
C4 C5 C6 126.3(7) .
C17 C5 C6 116.8(6) .
C7 C6 C14 116.5(7) .
C7 C6 C5 126.2(6) .
C14 C6 C5 117.1(6) .
C6 C7 C8 120.6(6) .
C6 C7 I2 123.2(6) .
C8 C7 I2 115.3(6) .
C9 C8 C7 121.7(7) .
C9 C8 H8A 119.1 .
C7 C8 H8A 119.1 .
C8 C9 C13 119.4(7) .
C8 C9 C10 118.6(6) .
C13 C9 C10 122.0(6) .
O3 C10 N2 121.7(7) .
O3 C10 C9 123.4(6) .
N2 C10 C9 114.9(6) .
O4 C11 N2 118.9(6) .
O4 C11 C12 123.1(5) .
N2 C11 C12 117.9(5) .
C24 C12 C13 119.3(6) .
C24 C12 C11 122.3(5) .
C13 C12 C11 117.8(5) .
C14 C13 C9 118.2(6) .
C14 C13 C12 120.8(6) .
C9 C13 C12 120.9(6) .
C13 C14 C15 118.1(6) .
C13 C14 C6 121.9(6) .
C15 C14 C6 119.5(6) .
C14 C15 C23 120.2(6) .
C14 C15 C16 120.4(6) .
C23 C15 C16 119.4(6) .
C22 C16 C17 120.5(6) .
C22 C16 C15 121.7(5) .
C17 C16 C15 117.6(6) .
C18 C17 C5 120.0(6) .
C18 C17 C16 118.7(6) .
C5 C17 C16 121.0(7) .
C2 C18 C17 119.8(6) .
C2 C18 C19 120.5(7) .
C17 C18 C19 119.6(6) .
C21 C19 C18 120.7(6) .
C21 C19 C20 119.0(6) .
C18 C19 C20 120.3(5) .
O2 C20 N1 121.4(6) .
O2 C20 C19 123.4(5) .
N1 C20 C19 115.2(6) .
C19 C21 C22 120.9(6) .
C19 C21 H21A 119.6 .
C22 C21 H21A 119.6 .
C21 C22 C16 119.2(5) .
C21 C22 C24 122.8(5) 2_655
C16 C22 C24 117.8(6) 2_655
C15 C23 C24 119.8(5) .
C15 C23 C23 118.5(7) 2_655
C24 C23 C23 121.4(7) 2_655
C12 C24 C23 117.8(5) .
C12 C24 C22 125.8(6) 2_655
C23 C24 C22 116.3(5) 2_655
C26 C25 C30 122.2(7) .
C26 C25 N1 119.0(7) .
C30 C25 N1 118.9(7) .
C27 C26 C25 117.5(8) .
C27 C26 C31 121.0(8) .
C25 C26 C31 121.5(7) .
C26 C27 C28 121.8(9) .
C26 C27 H27A 119.1 .
C28 C27 H27A 119.1 .
C29 C28 C27 120.1(9) .
C29 C28 H28A 120.0 .
C27 C28 H28A 120.0 .
C28 C29 C30 120.7(9) .
C28 C29 H29A 119.7 .
C30 C29 H29A 119.7 .
C29 C30 C25 117.9(9) .
C29 C30 C34 119.5(9) .
C25 C30 C34 122.6(8) .
C33 C31 C26 111.6(7) .
C33 C31 C32 108.8(7) .
C26 C31 C32 113.3(7) .
C33 C31 H31A 107.7 .
C26 C31 H31A 107.7 .
C32 C31 H31A 107.7 .
C31 C32 H32A 109.5 .
C31 C32 H32B 109.5 .
H32A C32 H32B 109.5 .
C31 C32 H32C 109.5 .
H32A C32 H32C 109.5 .
H32B C32 H32C 109.5 .
C31 C33 H33A 109.5 .
C31 C33 H33B 109.5 .
H33A C33 H33B 109.5 .
C31 C33 H33C 109.5 .
H33A C33 H33C 109.5 .
H33B C33 H33C 109.5 .
C30 C34 C35 113.1(9) .
C30 C34 C36 110.9(8) .
C35 C34 C36 111.6(8) .
C30 C34 H34A 106.9 .
C35 C34 H34A 106.9 .
C36 C34 H34A 106.9 .
C34 C35 H35A 109.5 .
C34 C35 H35B 109.5 .
H35A C35 H35B 109.5 .
C34 C35 H35C 109.5 .
H35A C35 H35C 109.5 .
H35B C35 H35C 109.5 .
C34 C36 H36A 109.5 .
C34 C36 H36B 109.5 .
H36A C36 H36B 109.5 .
C34 C36 H36C 109.5 .
H36A C36 H36C 109.5 .
H36B C36 H36C 109.5 .
C42 C37 C38 122.9(7) .
C42 C37 N2 119.5(6) .
C38 C37 N2 117.6(6) .
C39 C38 C37 117.7(7) .
C39 C38 C43 119.9(6) .
C37 C38 C43 122.4(6) .
C40 C39 C38 120.4(7) .
C40 C39 H39A 119.8 .
C38 C39 H39A 119.8 .
C39 C40 C41 121.5(8) .
C39 C40 H40A 119.3 .
C41 C40 H40A 119.3 .
C40 C41 C42 119.9(7) .
C40 C41 H41A 120.1 .
C42 C41 H41A 120.1 .
C41 C42 C37 117.5(7) .
C41 C42 C46 121.0(7) .
C37 C42 C46 121.5(7) .
C44 C43 C45 111.5(6) .
C44 C43 C38 111.8(6) .
C45 C43 C38 110.0(6) .
C44 C43 H43A 107.8 .
C45 C43 H43A 107.8 .
C38 C43 H43A 107.8 .
C43 C44 H44A 109.5 .
C43 C44 H44B 109.5 .
H44A C44 H44B 109.5 .
C43 C44 H44C 109.5 .
H44A C44 H44C 109.5 .
H44B C44 H44C 109.5 .
C43 C45 H45A 109.5 .
C43 C45 H45B 109.5 .
H45A C45 H45B 109.5 .
C43 C45 H45C 109.5 .
H45A C45 H45C 109.5 .
H45B C45 H45C 109.5 .
C42 C46 C48 113.0(8) .
C42 C46 C47 108.9(7) .
C48 C46 C47 109.0(8) .
C42 C46 H46A 108.6 .
C48 C46 H46A 108.6 .
C47 C46 H46A 108.6 .
C46 C47 H47A 109.5 .
C46 C47 H47B 109.5 .
H47A C47 H47B 109.5 .
C46 C47 H47C 109.5 .
H47A C47 H47C 109.5 .
H47B C47 H47C 109.5 .
C46 C48 H48A 109.5 .
C46 C48 H48B 109.5 .
H48A C48 H48B 109.5 .
C46 C48 H48C 109.5 .
H48A C48 H48C 109.5 .
H48B C48 H48C 109.5 .
C54 C49 C50 111.5(9) .
C54 C49 H49A 109.3 .
C50 C49 H49A 109.3 .
C54 C49 H49B 109.3 .
C50 C49 H49B 109.3 .
H49A C49 H49B 108.0 .
C49 C50 C51 112.1(9) .
C49 C50 H50A 109.2 .
C51 C50 H50A 109.2 .
C49 C50 H50B 109.2 .
C51 C50 H50B 109.2 .
H50A C50 H50B 107.9 .
C50 C51 C52 108.0(8) .
C50 C51 H51A 110.1 .
C52 C51 H51A 110.1 .
C50 C51 H51B 110.1 .
C52 C51 H51B 110.1 .
H51A C51 H51B 108.4 .
C53 C52 C51 113.7(8) .
C53 C52 H52A 108.8 .
C51 C52 H52A 108.8 .
C53 C52 H52B 108.8 .
C51 C52 H52B 108.8 .
H52A C52 H52B 107.7 .
C52 C53 C54 108.8(8) .
C52 C53 H53A 109.9 .
C54 C53 H53A 109.9 .
C52 C53 H53B 109.9 .
C54 C53 H53B 109.9 .
H53A C53 H53B 108.3 .
C49 C54 C53 112.2(8) .
C49 C54 H54A 109.2 .
C53 C54 H54A 109.2 .
C49 C54 H54B 109.2 .
C53 C54 H54B 109.2 .
H54A C54 H54B 107.9 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C4 2.105(7) .
I2 C7 2.093(7) .
O1 C1 1.210(9) .
O2 C20 1.210(8) .
O3 C10 1.205(8) .
O4 C11 1.214(8) .
N1 C1 1.393(9) .
N1 C20 1.416(8) .
N1 C25 1.459(9) .
N2 C11 1.399(7) .
N2 C10 1.408(8) .
N2 C37 1.459(9) .
C1 C2 1.478(11) .
C2 C3 1.382(10) .
C2 C18 1.396(9) .
C3 C4 1.383(12) .
C3 H3A 0.9500 .
C4 C5 1.403(11) .
C5 C17 1.420(9) .
C5 C6 1.470(11) .
C6 C7 1.386(11) .
C6 C14 1.440(9) .
C7 C8 1.401(12) .
C8 C9 1.383(10) .
C8 H8A 0.9500 .
C9 C13 1.416(9) .
C9 C10 1.481(11) .
C11 C12 1.496(9) .
C12 C24 1.398(8) .
C12 C13 1.428(8) .
C13 C14 1.400(10) .
C14 C15 1.407(9) .
C15 C23 1.409(8) .
C15 C16 1.438(9) .
C16 C22 1.410(8) .
C16 C17 1.434(8) .
C17 C18 1.408(10) .
C18 C19 1.421(9) .
C19 C21 1.382(8) .
C19 C20 1.488(9) .
C21 C22 1.408(9) .
C21 H21A 0.9500 .
C22 C24 1.478(8) 2_655
C23 C24 1.429(9) .
C23 C23 1.434(12) 2_655
C24 C22 1.478(8) 2_655
C25 C26 1.399(11) .
C25 C30 1.401(11) .
C26 C27 1.379(11) .
C26 C31 1.513(11) .
C27 C28 1.384(13) .
C27 H27A 0.9500 .
C28 C29 1.376(14) .
C28 H28A 0.9500 .
C29 C30 1.396(12) .
C29 H29A 0.9500 .
C30 C34 1.515(13) .
C31 C33 1.488(12) .
C31 C32 1.531(11) .
C31 H31A 1.0000 .
C32 H32A 0.9800 .
C32 H32B 0.9800 .
C32 H32C 0.9800 .
C33 H33A 0.9800 .
C33 H33B 0.9800 .
C33 H33C 0.9800 .
C34 C35 1.542(12) .
C34 C36 1.557(13) .
C34 H34A 1.0000 .
C35 H35A 0.9800 .
C35 H35B 0.9800 .
C35 H35C 0.9800 .
C36 H36A 0.9800 .
C36 H36B 0.9800 .
C36 H36C 0.9800 .
C37 C42 1.398(10) .
C37 C38 1.402(10) .
C38 C39 1.382(10) .
C38 C43 1.544(10) .
C39 C40 1.382(10) .
C39 H39A 0.9500 .
C40 C41 1.388(11) .
C40 H40A 0.9500 .
C41 C42 1.397(11) .
C41 H41A 0.9500 .
C42 C46 1.519(11) .
C43 C44 1.523(10) .
C43 C45 1.532(10) .
C43 H43A 1.0000 .
C44 H44A 0.9800 .
C44 H44B 0.9800 .
C44 H44C 0.9800 .
C45 H45A 0.9800 .
C45 H45B 0.9800 .
C45 H45C 0.9800 .
C46 C48 1.528(12) .
C46 C47 1.540(12) .
C46 H46A 1.0000 .
C47 H47A 0.9800 .
C47 H47B 0.9800 .
C47 H47C 0.9800 .
C48 H48A 0.9800 .
C48 H48B 0.9800 .
C48 H48C 0.9800 .
C49 C54 1.487(14) .
C49 C50 1.524(9) .
C49 H49A 0.9900 .
C49 H49B 0.9900 .
C50 C51 1.525(9) .
C50 H50A 0.9900 .
C50 H50B 0.9900 .
C51 C52 1.533(8) .
C51 H51A 0.9900 .
C51 H51B 0.9900 .
C52 C53 1.522(8) .
C52 H52A 0.9900 .
C52 H52B 0.9900 .
C53 C54 1.523(8) .
C53 H53A 0.9900 .
C53 H53B 0.9900 .
C54 H54A 0.9900 .
C54 H54B 0.9900 .
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_4
C20 N1 C1 O1 -166.0(7) . .
C25 N1 C1 O1 8.9(11) . .
C20 N1 C1 C2 15.4(11) . .
C25 N1 C1 C2 -169.7(7) . .
O1 C1 C2 C3 0.3(13) . .
N1 C1 C2 C3 178.8(7) . .
O1 C1 C2 C18 173.9(8) . .
N1 C1 C2 C18 -7.5(11) . .
C18 C2 C3 C4 6.7(13) . .
C1 C2 C3 C4 -179.6(8) . .
C2 C3 C4 C5 4.0(14) . .
C2 C3 C4 I1 -166.3(7) . .
C3 C4 C5 C17 -14.7(12) . .
I1 C4 C5 C17 154.9(6) . .
C3 C4 C5 C6 169.6(8) . .
I1 C4 C5 C6 -20.7(12) . .
C4 C5 C6 C7 -40.4(12) . .
C17 C5 C6 C7 144.0(8) . .
C4 C5 C6 C14 145.6(8) . .
C17 C5 C6 C14 -30.1(9) . .
C14 C6 C7 C8 -12.1(11) . .
C5 C6 C7 C8 173.8(7) . .
C14 C6 C7 I2 156.7(6) . .
C5 C6 C7 I2 -17.4(11) . .
C6 C7 C8 C9 2.1(13) . .
I2 C7 C8 C9 -167.5(6) . .
C7 C8 C9 C13 5.1(11) . .
C7 C8 C9 C10 -178.0(7) . .
C11 N2 C10 O3 -175.9(6) . .
C37 N2 C10 O3 1.2(9) . .
C11 N2 C10 C9 3.4(9) . .
C37 N2 C10 C9 -179.5(5) . .
C8 C9 C10 O3 4.2(10) . .
C13 C9 C10 O3 -179.0(6) . .
C8 C9 C10 N2 -175.1(6) . .
C13 C9 C10 N2 1.7(9) . .
C10 N2 C11 O4 168.6(6) . .
C37 N2 C11 O4 -8.5(9) . .
C10 N2 C11 C12 -9.0(9) . .
C37 N2 C11 C12 173.9(5) . .
O4 C11 C12 C24 3.1(10) . .
N2 C11 C12 C24 -179.5(6) . .
O4 C11 C12 C13 -168.1(6) . .
N2 C11 C12 C13 9.4(8) . .
C8 C9 C13 C14 -1.4(10) . .
C10 C9 C13 C14 -178.2(6) . .
C8 C9 C13 C12 176.1(6) . .
C10 C9 C13 C12 -0.7(9) . .
C24 C12 C13 C14 1.2(9) . .
C11 C12 C13 C14 172.6(6) . .
C24 C12 C13 C9 -176.3(6) . .
C11 C12 C13 C9 -4.9(9) . .
C9 C13 C14 C15 162.3(6) . .
C12 C13 C14 C15 -15.3(9) . .
C9 C13 C14 C6 -9.2(10) . .
C12 C13 C14 C6 173.2(6) . .
C7 C6 C14 C13 15.9(10) . .
C5 C6 C14 C13 -169.5(6) . .
C7 C6 C14 C15 -155.5(7) . .
C5 C6 C14 C15 19.2(10) . .
C13 C14 C15 C23 11.9(9) . .
C6 C14 C15 C23 -176.4(6) . .
C13 C14 C15 C16 -166.3(6) . .
C6 C14 C15 C16 5.4(10) . .
C14 C15 C16 C22 166.6(6) . .
C23 C15 C16 C22 -11.7(9) . .
C14 C15 C16 C17 -18.8(9) . .
C23 C15 C16 C17 162.9(6) . .
C4 C5 C17 C18 15.0(10) . .
C6 C5 C17 C18 -168.9(6) . .
C4 C5 C17 C16 -159.0(7) . .
C6 C5 C17 C16 17.1(10) . .
C22 C16 C17 C18 7.6(9) . .
C15 C16 C17 C18 -167.0(6) . .
C22 C16 C17 C5 -178.3(6) . .
C15 C16 C17 C5 7.0(10) . .
C3 C2 C18 C17 -6.2(11) . .
C1 C2 C18 C17 -179.8(7) . .
C3 C2 C18 C19 170.2(7) . .
C1 C2 C18 C19 -3.5(11) . .
C5 C17 C18 C2 -4.9(10) . .
C16 C17 C18 C2 169.2(6) . .
C5 C17 C18 C19 178.7(6) . .
C16 C17 C18 C19 -7.2(10) . .
C2 C18 C19 C21 -172.7(6) . .
C17 C18 C19 C21 3.6(10) . .
C2 C18 C19 C20 7.7(10) . .
C17 C18 C19 C20 -175.9(6) . .
C1 N1 C20 O2 169.5(7) . .
C25 N1 C20 O2 -5.4(10) . .
C1 N1 C20 C19 -11.3(10) . .
C25 N1 C20 C19 173.8(6) . .
C21 C19 C20 O2 -1.3(10) . .
C18 C19 C20 O2 178.3(6) . .
C21 C19 C20 N1 179.6(6) . .
C18 C19 C20 N1 -0.9(9) . .
C18 C19 C21 C22 -0.3(9) . .
C20 C19 C21 C22 179.3(6) . .
C19 C21 C22 C16 0.7(9) . .
C19 C21 C22 C24 174.5(6) . 2_655
C17 C16 C22 C21 -4.4(9) . .
C15 C16 C22 C21 170.1(6) . .
C17 C16 C22 C24 -178.5(6) . 2_655
C15 C16 C22 C24 -4.0(9) . 2_655
C14 C15 C23 C24 5.2(9) . .
C16 C15 C23 C24 -176.6(6) . .
C14 C15 C23 C23 -168.9(4) . 2_655
C16 C15 C23 C23 9.4(7) . 2_655
C13 C12 C24 C23 15.8(9) . .
C11 C12 C24 C23 -155.2(6) . .
C13 C12 C24 C22 -165.6(6) . 2_655
C11 C12 C24 C22 23.4(9) . 2_655
C15 C23 C24 C12 -19.1(9) . .
C23 C23 C24 C12 154.8(4) 2_655 .
C15 C23 C24 C22 162.1(5) . 2_655
C23 C23 C24 C22 -23.9(6) 2_655 2_655
C1 N1 C25 C26 84.7(9) . .
C20 N1 C25 C26 -100.0(7) . .
C1 N1 C25 C30 -94.6(8) . .
C20 N1 C25 C30 80.7(8) . .
C30 C25 C26 C27 0.2(11) . .
N1 C25 C26 C27 -179.1(6) . .
C30 C25 C26 C31 179.3(7) . .
N1 C25 C26 C31 -0.1(10) . .
C25 C26 C27 C28 -1.6(11) . .
C31 C26 C27 C28 179.4(7) . .
C26 C27 C28 C29 1.8(12) . .
C27 C28 C29 C30 -0.6(12) . .
C28 C29 C30 C25 -0.7(11) . .
C28 C29 C30 C34 -179.6(7) . .
C26 C25 C30 C29 0.9(11) . .
N1 C25 C30 C29 -179.8(6) . .
C26 C25 C30 C34 179.7(7) . .
N1 C25 C30 C34 -0.9(10) . .
C27 C26 C31 C33 83.7(10) . .
C25 C26 C31 C33 -95.3(9) . .
C27 C26 C31 C32 -39.5(10) . .
C25 C26 C31 C32 141.5(7) . .
C29 C30 C34 C35 63.4(11) . .
C25 C30 C34 C35 -115.4(9) . .
C29 C30 C34 C36 -62.9(11) . .
C25 C30 C34 C36 118.3(9) . .
C11 N2 C37 C42 82.1(7) . .
C10 N2 C37 C42 -95.3(7) . .
C11 N2 C37 C38 -99.1(7) . .
C10 N2 C37 C38 83.6(7) . .
C42 C37 C38 C39 -3.1(10) . .
N2 C37 C38 C39 178.1(6) . .
C42 C37 C38 C43 177.6(6) . .
N2 C37 C38 C43 -1.3(9) . .
C37 C38 C39 C40 3.4(10) . .
C43 C38 C39 C40 -177.2(6) . .
C38 C39 C40 C41 -0.7(11) . .
C39 C40 C41 C42 -2.6(11) . .
C40 C41 C42 C37 2.9(10) . .
C40 C41 C42 C46 -178.3(6) . .
C38 C37 C42 C41 -0.1(10) . .
N2 C37 C42 C41 178.7(6) . .
C38 C37 C42 C46 -178.9(6) . .
N2 C37 C42 C46 -0.1(9) . .
C39 C38 C43 C44 -66.3(9) . .
C37 C38 C43 C44 113.1(8) . .
C39 C38 C43 C45 58.2(9) . .
C37 C38 C43 C45 -122.5(7) . .
C41 C42 C46 C48 45.7(9) . .
C37 C42 C46 C48 -135.6(8) . .
C41 C42 C46 C47 -75.6(10) . .
C37 C42 C46 C47 103.1(10) . .
C54 C49 C50 C51 -56.3(12) . .
C49 C50 C51 C52 54.6(12) . .
C50 C51 C52 C53 -56.3(12) . .
C51 C52 C53 C54 56.5(11) . .
C50 C49 C54 C53 56.2(12) . .
C52 C53 C54 C49 -55.4(12) . .
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
1 0.000 0.500 -0.001 2250.1 227.5
2 0.500 0.000 0.012 2250.1 227.5
