#------------------------------------------------------------------------------
#$Date: 2019-11-07 21:47:43 +0200 (Thu, 07 Nov 2019) $
#$Revision: 223610 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/24/7232473.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_7232473
loop_
_publ_author_name
'Koppireddi, Satish'
'Liu, Chuan-Zhi'
'Wang, Hui'
'Zhang, Dan-Wei'
'Li, Zhan-Ting'
_publ_section_title
;
 Halogen and hydrogen bonding-driven self-assembly of supramolecular
 macrocycles and double helices from hydrogen-bonded arylamide foldamers
;
_journal_issue                   16
_journal_name_full               CrystEngComm
_journal_page_first              2626
_journal_paper_doi               10.1039/C8CE02187B
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         '1.5(C6 F4 I2), C34 H46 N4 O6'
_chemical_formula_sum            'C43 H46 F6 I3 N4 O6'
_chemical_formula_weight         1209.54
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-03-02
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-12-26 deposited with the CCDC.    2019-03-06 downloaded from the CCDC.
;
_cell_angle_alpha                116.2490(10)
_cell_angle_beta                 96.2380(10)
_cell_angle_gamma                100.8410(10)
_cell_formula_units_Z            2
_cell_length_a                   9.3189(3)
_cell_length_b                   16.8147(5)
_cell_length_c                   18.3190(6)
_cell_measurement_reflns_used    9078
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.13
_cell_measurement_theta_min      2.28
_cell_volume                     2467.84(14)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS-1997 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            28784
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.010
_diffrn_reflns_theta_max         25.010
_diffrn_reflns_theta_min         1.374
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.969
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6876
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0602 before and 0.0425 after correction. The Ratio of minimum to maximum transmission is 0.9221. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1186
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.847
_refine_diff_density_min         -0.651
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     567
_refine_ls_number_reflns         8618
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0359
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0412P)²+2.2823P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.0919
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6635
_reflns_number_total             8618
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce02187b2.cif
_cod_data_source_block           z
_cod_depositor_comments
'Adding full bibliography for 7232470--7232474.cif.'
_cod_database_code               7232473
_shelx_shelxl_version_number     2016/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.770
_shelx_estimated_absorpt_t_min   0.546
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C26 \\sim C27: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002
3.a Ternary CH refined with riding coordinates:
 C18(H18), C22(H22), C26(H26), C30(H30)
3.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C21(H21A,H21B), C25(H25A,H25B), C29(H29A,H29B)
3.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N3(H3), C1(H1), C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C12(H12),
 C15(H15)
3.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C31(H31A,H31B,H31C), C32(H32A,
 H32B,H32C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
I1 I -0.00462(3) 0.83985(2) 0.04699(2) 0.05638(10) Uani 1 1 d . .
I2 I -0.15178(4) 0.63079(2) 0.29898(2) 0.06096(11) Uani 1 1 d . .
F1 F -0.0554(4) 0.62876(18) 0.01357(17) 0.0760(8) Uani 1 1 d . .
F2 F -0.0988(4) 0.55310(18) 0.11149(19) 0.0849(9) Uani 1 1 d . .
F3 F -0.1365(5) 0.8328(2) 0.32283(19) 0.1030(12) Uani 1 1 d . .
F4 F -0.0734(5) 0.9127(2) 0.2292(2) 0.1011(11) Uani 1 1 d . .
C35 C -0.0611(5) 0.7743(3) 0.1188(3) 0.0513(11) Uani 1 1 d . .
C36 C -0.0822(6) 0.8226(3) 0.1981(3) 0.0637(13) Uani 1 1 d . .
C37 C -0.1111(6) 0.7816(3) 0.2470(3) 0.0641(13) Uani 1 1 d . .
C38 C -0.1165(5) 0.6902(3) 0.2207(3) 0.0530(11) Uani 1 1 d . .
C39 C -0.0943(5) 0.6424(3) 0.1418(3) 0.0530(11) Uani 1 1 d . .
C40 C -0.0704(5) 0.6823(3) 0.0917(3) 0.0527(11) Uani 1 1 d . .
I3 I 0.05017(4) 0.84361(2) 0.57005(2) 0.06782(12) Uani 1 1 d . .
F5 F 0.2156(4) 0.9124(3) 0.4566(2) 0.1048(12) Uani 1 1 d . .
F6 F -0.1771(4) 0.9684(2) 0.5963(2) 0.0960(10) Uani 1 1 d . .
C41 C 0.1094(6) 0.9557(3) 0.4792(3) 0.0657(13) Uani 1 1 d . .
C42 C 0.0203(6) 0.9368(3) 0.5279(3) 0.0567(12) Uani 1 1 d . .
C43 C -0.0888(6) 0.9820(4) 0.5480(3) 0.0674(14) Uani 1 1 d . .
O1 O -0.3013(4) 0.4390(2) 0.55459(18) 0.0608(8) Uani 1 1 d . .
O2 O 0.1004(4) 0.7098(2) 0.63227(19) 0.0644(9) Uani 1 1 d . .
O3 O -0.0687(3) 0.5637(2) 0.74962(19) 0.0624(9) Uani 1 1 d . .
O4 O 0.3662(3) 0.7291(2) 0.97271(18) 0.0579(8) Uani 1 1 d . .
O5 O 0.5402(4) 0.8618(2) 0.84583(18) 0.0655(9) Uani 1 1 d . .
O6 O 0.6031(3) 0.9479(2) 1.13877(17) 0.0581(8) Uani 1 1 d . .
N1 N -0.1985(5) 0.5539(3) 0.4034(2) 0.0623(10) Uani 1 1 d . .
N2 N -0.0648(4) 0.5810(2) 0.6123(2) 0.0509(9) Uani 1 1 d . .
H2 H -0.091106 0.548115 0.636026 0.061 Uiso 1 1 calc R .
N3 N 0.5427(4) 0.8778(2) 0.97489(19) 0.0474(8) Uani 1 1 d . .
H3 H 0.497638 0.855037 1.002663 0.057 Uiso 1 1 calc R .
N4 N 0.8804(4) 1.0671(3) 1.0338(2) 0.0574(10) Uani 1 1 d . .
C1 C -0.1161(5) 0.5857(3) 0.4794(3) 0.0555(11) Uani 1 1 d . .
H1 H -0.031703 0.634773 0.497936 0.067 Uiso 1 1 calc R .
C2 C -0.1489(5) 0.5498(3) 0.5322(2) 0.0450(10) Uani 1 1 d . .
C3 C -0.2736(5) 0.4742(3) 0.5025(3) 0.0510(11) Uani 1 1 d . .
C4 C -0.3571(6) 0.4401(3) 0.4227(3) 0.0621(12) Uani 1 1 d . .
H4 H -0.439731 0.389367 0.400703 0.075 Uiso 1 1 calc R .
C5 C -0.3149(6) 0.4830(4) 0.3769(3) 0.0648(13) Uani 1 1 d . .
H5 H -0.372468 0.460409 0.323653 0.078 Uiso 1 1 calc R .
C6 C 0.9092(5) 1.0978(3) 1.1153(3) 0.0582(12) Uani 1 1 d . .
H6 H 0.993333 1.146538 1.147618 0.070 Uiso 1 1 calc R .
C7 C 0.8226(5) 1.0622(3) 1.1547(3) 0.0536(11) Uani 1 1 d . .
H7 H 0.847169 1.086845 1.212399 0.064 Uiso 1 1 calc R .
C8 C 0.6988(5) 0.9895(3) 1.1083(3) 0.0468(10) Uani 1 1 d . .
C9 C 0.6674(4) 0.9531(3) 1.0211(2) 0.0422(9) Uani 1 1 d . .
C10 C 0.7624(5) 0.9961(3) 0.9881(3) 0.0520(11) Uani 1 1 d . .
H10 H 0.742120 0.973652 0.930672 0.062 Uiso 1 1 calc R .
C11 C 0.1265(4) 0.6700(3) 0.7406(2) 0.0399(9) Uani 1 1 d . .
C12 C 0.2629(4) 0.7353(3) 0.7796(2) 0.0427(9) Uani 1 1 d . .
H12 H 0.303046 0.765415 0.751381 0.051 Uiso 1 1 calc R .
C13 C 0.3441(4) 0.7590(3) 0.8578(2) 0.0404(9) Uani 1 1 d . .
C14 C 0.2835(4) 0.7104(3) 0.8980(2) 0.0422(9) Uani 1 1 d . .
C15 C 0.1485(5) 0.6455(3) 0.8615(3) 0.0469(10) Uani 1 1 d . .
H15 H 0.110038 0.613510 0.888606 0.056 Uiso 1 1 calc R .
C16 C 0.0683(4) 0.6267(3) 0.7849(3) 0.0442(9) Uani 1 1 d . .
C17 C -0.4231(6) 0.3554(3) 0.5224(3) 0.0665(13) Uani 1 1 d . .
H17A H -0.405584 0.307441 0.472571 0.080 Uiso 1 1 calc R .
H17B H -0.517035 0.367268 0.507658 0.080 Uiso 1 1 calc R .
C18 C -0.4319(6) 0.3248(3) 0.5867(3) 0.0686(14) Uani 1 1 d . .
H18 H -0.452152 0.373877 0.635592 0.082 Uiso 1 1 calc R .
C19 C -0.2875(8) 0.3077(5) 0.6140(5) 0.113(2) Uani 1 1 d . .
H19A H -0.270978 0.255105 0.568834 0.169 Uiso 1 1 calc GR .
H19B H -0.293394 0.296400 0.660747 0.169 Uiso 1 1 calc GR .
H19C H -0.206052 0.360599 0.629864 0.169 Uiso 1 1 calc GR .
C20 C -0.5638(8) 0.2402(4) 0.5531(4) 0.107(2) Uani 1 1 d . .
H20A H -0.652667 0.253378 0.534925 0.160 Uiso 1 1 calc GR .
H20B H -0.577767 0.223760 0.596360 0.160 Uiso 1 1 calc GR .
H20C H -0.544131 0.189959 0.506980 0.160 Uiso 1 1 calc GR .
C21 C -0.1678(5) 0.5522(4) 0.8021(3) 0.0726(15) Uani 1 1 d . .
H21A H -0.118555 0.592396 0.860220 0.087 Uiso 1 1 calc R .
H21B H -0.188852 0.489327 0.792712 0.087 Uiso 1 1 calc R .
C22 C -0.3107(7) 0.5741(4) 0.7843(4) 0.0810(16) Uani 1 1 d . .
H22 H -0.356203 0.531156 0.725417 0.097 Uiso 1 1 calc R .
C23 C -0.2940(9) 0.6667(5) 0.7929(6) 0.131(3) Uani 1 1 d . .
H23A H -0.236397 0.711606 0.847476 0.196 Uiso 1 1 calc GR .
H23B H -0.391041 0.677047 0.785187 0.196 Uiso 1 1 calc GR .
H23C H -0.243552 0.671894 0.751561 0.196 Uiso 1 1 calc GR .
C24 C -0.4164(8) 0.5516(7) 0.8328(5) 0.134(3) Uani 1 1 d . .
H24A H -0.438093 0.487045 0.815920 0.202 Uiso 1 1 calc GR .
H24B H -0.507566 0.567260 0.822296 0.202 Uiso 1 1 calc GR .
H24C H -0.371184 0.586116 0.891276 0.202 Uiso 1 1 calc GR .
C25 C 0.3053(6) 0.6851(4) 1.0183(3) 0.0795(17) Uani 1 1 d . .
H25A H 0.260758 0.620282 0.980264 0.095 Uiso 1 1 calc R .
H25B H 0.226726 0.711659 1.041663 0.095 Uiso 1 1 calc R .
C26 C 0.4161(8) 0.6945(6) 1.0842(5) 0.123(2) Uani 1 1 d . U
H26 H 0.462620 0.760572 1.118695 0.148 Uiso 1 1 calc R .
C27 C 0.3420(8) 0.6625(6) 1.1397(5) 0.131(2) Uani 1 1 d . U
H27A H 0.274995 0.698977 1.163351 0.197 Uiso 1 1 calc GR .
H27B H 0.417244 0.669107 1.183729 0.197 Uiso 1 1 calc GR .
H27C H 0.286785 0.599038 1.107336 0.197 Uiso 1 1 calc GR .
C28 C 0.5369(9) 0.6524(7) 1.0598(5) 0.152(4) Uani 1 1 d . .
H28A H 0.497485 0.586937 1.027924 0.229 Uiso 1 1 calc GR .
H28B H 0.608481 0.667172 1.108748 0.229 Uiso 1 1 calc GR .
H28C H 0.584951 0.675367 1.026550 0.229 Uiso 1 1 calc GR .
C29 C 0.6204(6) 0.9939(4) 1.2292(3) 0.0689(14) Uani 1 1 d . .
H29A H 0.612579 1.056373 1.248376 0.083 Uiso 1 1 calc R .
H29B H 0.718249 0.996332 1.255669 0.083 Uiso 1 1 calc R .
C30 C 0.5013(6) 0.9422(4) 1.2521(3) 0.0789(16) Uani 1 1 d . .
H30 H 0.507988 0.878569 1.229599 0.095 Uiso 1 1 calc R .
C31 C 0.5296(10) 0.9854(7) 1.3477(4) 0.158(4) Uani 1 1 d . .
H31A H 0.623743 0.979510 1.368669 0.238 Uiso 1 1 calc GR .
H31B H 0.450736 0.954404 1.363051 0.238 Uiso 1 1 calc GR .
H31C H 0.531790 1.049359 1.371007 0.238 Uiso 1 1 calc GR .
C32 C 0.3508(8) 0.9415(7) 1.2172(5) 0.132(3) Uani 1 1 d . .
H32A H 0.342146 1.003501 1.239007 0.197 Uiso 1 1 calc GR .
H32B H 0.276912 0.906858 1.232162 0.197 Uiso 1 1 calc GR .
H32C H 0.335158 0.913821 1.157510 0.197 Uiso 1 1 calc GR .
C33 C 0.0530(5) 0.6562(3) 0.6574(2) 0.0437(9) Uani 1 1 d . .
C34 C 0.4841(5) 0.8363(3) 0.8921(2) 0.0436(9) Uani 1 1 d . .
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'
F F 0.0171 0.0103 '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'
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'
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
C36 C35 I1 121.3(3) . .
C36 C35 C40 115.9(4) . .
C40 C35 I1 122.6(3) . .
F4 C36 C35 119.5(4) . .
F4 C36 C37 118.8(4) . .
C37 C36 C35 121.8(4) . .
F3 C37 C36 118.2(4) . .
F3 C37 C38 119.5(4) . .
C36 C37 C38 122.2(4) . .
C37 C38 I2 121.4(3) . .
C39 C38 I2 122.9(3) . .
C39 C38 C37 115.7(4) . .
F2 C39 C38 119.3(4) . .
F2 C39 C40 118.5(4) . .
C38 C39 C40 122.2(4) . .
F1 C40 C35 120.0(4) . .
F1 C40 C39 117.9(4) . .
C39 C40 C35 122.0(4) . .
F5 C41 C42 120.1(4) . .
F5 C41 C43 119.0(5) . 2_576
C43 C41 C42 120.9(5) 2_576 .
C41 C42 I3 121.5(4) . .
C43 C42 I3 120.9(3) . .
C43 C42 C41 117.6(4) . .
F6 C43 C41 117.7(5) . 2_576
F6 C43 C42 120.8(4) . .
C42 C43 C41 121.5(5) . 2_576
C3 O1 C17 117.4(3) . .
C16 O3 C21 120.0(3) . .
C14 O4 C25 119.3(3) . .
C8 O6 C29 116.0(3) . .
C5 N1 C1 117.7(4) . .
C2 N2 H2 115.7 . .
C33 N2 H2 115.7 . .
C33 N2 C2 128.6(3) . .
C9 N3 H3 115.9 . .
C34 N3 H3 115.9 . .
C34 N3 C9 128.2(3) . .
C6 N4 C10 117.6(4) . .
N1 C1 H1 118.2 . .
N1 C1 C2 123.6(4) . .
C2 C1 H1 118.2 . .
N2 C2 C3 117.1(3) . .
C1 C2 N2 125.3(4) . .
C1 C2 C3 117.5(4) . .
O1 C3 C2 116.4(4) . .
O1 C3 C4 125.0(4) . .
C4 C3 C2 118.6(4) . .
C3 C4 H4 120.8 . .
C5 C4 C3 118.3(4) . .
C5 C4 H4 120.8 . .
N1 C5 C4 124.1(4) . .
N1 C5 H5 117.9 . .
C4 C5 H5 117.9 . .
N4 C6 H6 118.1 . .
N4 C6 C7 123.8(4) . .
C7 C6 H6 118.1 . .
C6 C7 H7 120.4 . .
C6 C7 C8 119.3(4) . .
C8 C7 H7 120.4 . .
O6 C8 C7 125.7(4) . .
O6 C8 C9 115.8(4) . .
C7 C8 C9 118.5(4) . .
N3 C9 C8 117.6(3) . .
C10 C9 N3 125.4(4) . .
C10 C9 C8 116.9(4) . .
N4 C10 C9 123.9(4) . .
N4 C10 H10 118.1 . .
C9 C10 H10 118.1 . .
C12 C11 C16 116.4(3) . .
C12 C11 C33 117.0(3) . .
C16 C11 C33 126.6(4) . .
C11 C12 H12 117.7 . .
C11 C12 C13 124.6(3) . .
C13 C12 H12 117.7 . .
C12 C13 C14 116.6(4) . .
C12 C13 C34 116.7(3) . .
C14 C13 C34 126.6(3) . .
O4 C14 C13 117.3(3) . .
O4 C14 C15 122.3(3) . .
C15 C14 C13 120.4(4) . .
C14 C15 H15 119.5 . .
C14 C15 C16 121.0(4) . .
C16 C15 H15 119.5 . .
O3 C16 C11 118.2(3) . .
O3 C16 C15 120.9(3) . .
C15 C16 C11 120.9(4) . .
O1 C17 H17A 109.7 . .
O1 C17 H17B 109.7 . .
O1 C17 C18 109.6(4) . .
H17A C17 H17B 108.2 . .
C18 C17 H17A 109.7 . .
C18 C17 H17B 109.7 . .
C17 C18 H18 107.9 . .
C17 C18 C19 112.3(5) . .
C17 C18 C20 108.6(5) . .
C19 C18 H18 107.9 . .
C19 C18 C20 112.2(5) . .
C20 C18 H18 107.9 . .
C18 C19 H19A 109.5 . .
C18 C19 H19B 109.5 . .
C18 C19 H19C 109.5 . .
H19A C19 H19B 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C18 C20 H20A 109.5 . .
C18 C20 H20B 109.5 . .
C18 C20 H20C 109.5 . .
H20A C20 H20B 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
O3 C21 H21A 109.4 . .
O3 C21 H21B 109.4 . .
O3 C21 C22 111.3(4) . .
H21A C21 H21B 108.0 . .
C22 C21 H21A 109.4 . .
C22 C21 H21B 109.4 . .
C21 C22 H22 105.9 . .
C21 C22 C24 109.7(5) . .
C23 C22 C21 114.9(6) . .
C23 C22 H22 105.9 . .
C23 C22 C24 113.7(7) . .
C24 C22 H22 105.9 . .
C22 C23 H23A 109.5 . .
C22 C23 H23B 109.5 . .
C22 C23 H23C 109.5 . .
H23A C23 H23B 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
C22 C24 H24A 109.5 . .
C22 C24 H24B 109.5 . .
C22 C24 H24C 109.5 . .
H24A C24 H24B 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
O4 C25 H25A 109.1 . .
O4 C25 H25B 109.1 . .
O4 C25 C26 112.4(4) . .
H25A C25 H25B 107.8 . .
C26 C25 H25A 109.1 . .
C26 C25 H25B 109.1 . .
C25 C26 H26 106.2 . .
C25 C26 C27 110.2(6) . .
C25 C26 C28 116.6(7) . .
C27 C26 H26 106.2 . .
C28 C26 H26 106.2 . .
C28 C26 C27 110.7(7) . .
C26 C27 H27A 109.5 . .
C26 C27 H27B 109.5 . .
C26 C27 H27C 109.5 . .
H27A C27 H27B 109.5 . .
H27A C27 H27C 109.5 . .
H27B C27 H27C 109.5 . .
C26 C28 H28A 109.5 . .
C26 C28 H28B 109.5 . .
C26 C28 H28C 109.5 . .
H28A C28 H28B 109.5 . .
H28A C28 H28C 109.5 . .
H28B C28 H28C 109.5 . .
O6 C29 H29A 109.8 . .
O6 C29 H29B 109.8 . .
O6 C29 C30 109.3(4) . .
H29A C29 H29B 108.3 . .
C30 C29 H29A 109.8 . .
C30 C29 H29B 109.8 . .
C29 C30 H30 108.4 . .
C29 C30 C31 108.9(5) . .
C31 C30 H30 108.4 . .
C32 C30 C29 111.6(5) . .
C32 C30 H30 108.4 . .
C32 C30 C31 110.8(6) . .
C30 C31 H31A 109.5 . .
C30 C31 H31B 109.5 . .
C30 C31 H31C 109.5 . .
H31A C31 H31B 109.5 . .
H31A C31 H31C 109.5 . .
H31B C31 H31C 109.5 . .
C30 C32 H32A 109.5 . .
C30 C32 H32B 109.5 . .
C30 C32 H32C 109.5 . .
H32A C32 H32B 109.5 . .
H32A C32 H32C 109.5 . .
H32B C32 H32C 109.5 . .
O2 C33 N2 122.8(4) . .
O2 C33 C11 120.4(4) . .
N2 C33 C11 116.7(3) . .
O5 C34 N3 121.8(4) . .
O5 C34 C13 120.1(4) . .
N3 C34 C13 118.0(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C35 2.106(4) .
I2 C38 2.100(4) .
F1 C40 1.353(5) .
F2 C39 1.341(5) .
F3 C37 1.348(5) .
F4 C36 1.344(5) .
C35 C36 1.374(6) .
C35 C40 1.381(6) .
C36 C37 1.371(7) .
C37 C38 1.381(6) .
C38 C39 1.371(6) .
C39 C40 1.369(6) .
I3 C42 2.078(4) .
F5 C41 1.332(6) .
F6 C43 1.335(5) .
C41 C42 1.377(7) .
C41 C43 1.378(7) 2_576
C42 C43 1.369(7) .
O1 C3 1.350(5) .
O1 C17 1.460(5) .
O2 C33 1.218(5) .
O3 C16 1.370(5) .
O3 C21 1.451(5) .
O4 C14 1.365(5) .
O4 C25 1.435(5) .
O5 C34 1.230(5) .
O6 C8 1.347(5) .
O6 C29 1.459(5) .
N1 C1 1.330(5) .
N1 C5 1.312(6) .
N2 H2 0.8600 .
N2 C2 1.398(5) .
N2 C33 1.358(5) .
N3 H3 0.8600 .
N3 C9 1.398(5) .
N3 C34 1.350(5) .
N4 C6 1.322(6) .
N4 C10 1.326(5) .
C1 H1 0.9300 .
C1 C2 1.381(6) .
C2 C3 1.399(6) .
C3 C4 1.383(6) .
C4 H4 0.9300 .
C4 C5 1.371(6) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C6 C7 1.363(6) .
C7 H7 0.9300 .
C7 C8 1.373(6) .
C8 C9 1.407(5) .
C9 C10 1.390(5) .
C10 H10 0.9300 .
C11 C12 1.383(5) .
C11 C16 1.397(5) .
C11 C33 1.498(5) .
C12 H12 0.9300 .
C12 C13 1.390(5) .
C13 C14 1.407(5) .
C13 C34 1.499(5) .
C14 C15 1.370(6) .
C15 H15 0.9300 .
C15 C16 1.386(5) .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
C17 C18 1.484(7) .
C18 H18 0.9800 .
C18 C19 1.507(8) .
C18 C20 1.523(7) .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
C21 H21A 0.9700 .
C21 H21B 0.9700 .
C21 C22 1.487(7) .
C22 H22 0.9800 .
C22 C23 1.470(8) .
C22 C24 1.500(8) .
C23 H23A 0.9600 .
C23 H23B 0.9600 .
C23 H23C 0.9600 .
C24 H24A 0.9600 .
C24 H24B 0.9600 .
C24 H24C 0.9600 .
C25 H25A 0.9700 .
C25 H25B 0.9700 .
C25 C26 1.431(8) .
C26 H26 0.9800 .
C26 C27 1.517(8) .
C26 C28 1.448(10) .
C27 H27A 0.9600 .
C27 H27B 0.9600 .
C27 H27C 0.9600 .
C28 H28A 0.9600 .
C28 H28B 0.9600 .
C28 H28C 0.9600 .
C29 H29A 0.9700 .
C29 H29B 0.9700 .
C29 C30 1.491(7) .
C30 H30 0.9800 .
C30 C31 1.538(8) .
C30 C32 1.473(9) .
C31 H31A 0.9600 .
C31 H31B 0.9600 .
C31 H31C 0.9600 .
C32 H32A 0.9600 .
C32 H32B 0.9600 .
C32 H32C 0.9600 .
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
I1 C35 C36 F4 3.1(7) . .
I1 C35 C36 C37 -176.5(4) . .
I1 C35 C40 F1 -5.7(6) . .
I1 C35 C40 C39 174.2(3) . .
I2 C38 C39 F2 1.8(6) . .
I2 C38 C39 C40 -179.5(4) . .
F2 C39 C40 F1 1.2(6) . .
F2 C39 C40 C35 -178.7(4) . .
F3 C37 C38 I2 -3.4(7) . .
F3 C37 C38 C39 177.9(4) . .
F4 C36 C37 F3 3.1(8) . .
F4 C36 C37 C38 -177.6(5) . .
C35 C36 C37 F3 -177.3(5) . .
C35 C36 C37 C38 2.0(8) . .
C36 C35 C40 F1 178.1(4) . .
C36 C35 C40 C39 -2.0(7) . .
C36 C37 C38 I2 177.3(4) . .
C36 C37 C38 C39 -1.4(8) . .
C37 C38 C39 F2 -179.6(4) . .
C37 C38 C39 C40 -0.9(7) . .
C38 C39 C40 F1 -177.5(4) . .
C38 C39 C40 C35 2.6(7) . .
C40 C35 C36 F4 179.3(5) . .
C40 C35 C36 C37 -0.2(8) . .
I3 C42 C43 F6 1.0(7) . .
I3 C42 C43 C41 179.7(4) . 2_576
F5 C41 C42 I3 1.5(7) . .
F5 C41 C42 C43 -178.9(5) . .
C41 C42 C43 F6 -178.6(5) . .
C41 C42 C43 C41 0.0(9) . 2_576
C43 C41 C42 I3 -179.7(4) 2_576 .
C43 C41 C42 C43 0.0(9) 2_576 .
O1 C3 C4 C5 -179.7(5) . .
O1 C17 C18 C19 -57.9(6) . .
O1 C17 C18 C20 177.5(5) . .
O3 C21 C22 C23 -56.6(8) . .
O3 C21 C22 C24 173.8(6) . .
O4 C14 C15 C16 -178.8(4) . .
O4 C25 C26 C27 169.7(6) . .
O4 C25 C26 C28 -63.1(10) . .
O6 C8 C9 N3 -0.5(6) . .
O6 C8 C9 C10 178.6(4) . .
O6 C29 C30 C31 174.4(6) . .
O6 C29 C30 C32 -62.9(7) . .
N1 C1 C2 N2 179.7(4) . .
N1 C1 C2 C3 1.8(7) . .
N2 C2 C3 O1 0.5(6) . .
N2 C2 C3 C4 -178.3(4) . .
N3 C9 C10 N4 -179.6(4) . .
N4 C6 C7 C8 0.8(7) . .
C1 N1 C5 C4 0.3(8) . .
C1 C2 C3 O1 178.5(4) . .
C1 C2 C3 C4 -0.3(7) . .
C2 N2 C33 O2 1.5(7) . .
C2 N2 C33 C11 -177.1(4) . .
C2 C3 C4 C5 -1.0(7) . .
C3 O1 C17 C18 177.3(4) . .
C3 C4 C5 N1 1.1(8) . .
C5 N1 C1 C2 -1.9(7) . .
C6 N4 C10 C9 0.7(7) . .
C6 C7 C8 O6 -179.7(4) . .
C6 C7 C8 C9 1.3(7) . .
C7 C8 C9 N3 178.6(4) . .
C7 C8 C9 C10 -2.3(6) . .
C8 O6 C29 C30 176.7(4) . .
C8 C9 C10 N4 1.3(7) . .
C9 N3 C34 O5 1.1(7) . .
C9 N3 C34 C13 -177.0(4) . .
C10 N4 C6 C7 -1.8(7) . .
C11 C12 C13 C14 2.0(6) . .
C11 C12 C13 C34 -175.6(4) . .
C12 C11 C16 O3 178.1(4) . .
C12 C11 C16 C15 -3.4(6) . .
C12 C11 C33 O2 -11.0(6) . .
C12 C11 C33 N2 167.7(4) . .
C12 C13 C14 O4 176.3(4) . .
C12 C13 C14 C15 -2.1(6) . .
C12 C13 C34 O5 -16.1(6) . .
C12 C13 C34 N3 162.0(4) . .
C13 C14 C15 C16 -0.5(6) . .
C14 O4 C25 C26 166.3(6) . .
C14 C13 C34 O5 166.6(4) . .
C14 C13 C34 N3 -15.3(6) . .
C14 C15 C16 O3 -178.2(4) . .
C14 C15 C16 C11 3.4(7) . .
C16 O3 C21 C22 118.6(5) . .
C16 C11 C12 C13 0.7(6) . .
C16 C11 C33 O2 165.9(4) . .
C16 C11 C33 N2 -15.5(6) . .
C17 O1 C3 C2 -174.9(4) . .
C17 O1 C3 C4 3.9(7) . .
C21 O3 C16 C11 -148.1(4) . .
C21 O3 C16 C15 33.5(6) . .
C25 O4 C14 C13 176.5(4) . .
C25 O4 C14 C15 -5.1(6) . .
C29 O6 C8 C7 10.4(6) . .
C29 O6 C8 C9 -170.5(4) . .
C33 N2 C2 C1 7.6(7) . .
C33 N2 C2 C3 -174.5(4) . .
C33 C11 C12 C13 177.9(4) . .
C33 C11 C16 O3 1.2(6) . .
C33 C11 C16 C15 179.7(4) . .
C34 N3 C9 C8 174.2(4) . .
C34 N3 C9 C10 -4.9(7) . .
C34 C13 C14 O4 -6.4(6) . .
C34 C13 C14 C15 175.2(4) . .
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
1 0.284 0.181 0.313 79.5 14.8
2 -0.284 -0.181 0.687 79.5 16.1
3 0.227 0.808 0.294 8.8 0.0
4 0.773 0.192 0.706 8.8 0.0
