#------------------------------------------------------------------------------
#$Date: 2019-11-11 16:46:56 +0200 (Mon, 11 Nov 2019) $
#$Revision: 226611 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/51/4035126.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_4035126
loop_
_publ_author_name
'Gillen, Dermot M.'
'Hawes, Chris S.'
'Gunnlaugsson, Thorfinnur'
_publ_section_title
;
 Solution-State Anion Recognition, and Structural Studies, of a Series of
 Electron-Rich meta-Phenylene Bis(phenylurea) Receptors and Their
 Self-Assembled Structures.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10398
_journal_page_last               10408
_journal_paper_doi               10.1021/acs.joc.8b01481
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety
'6(C22 H22 N4 O4), 6(C16 H36 N), 2(C0.5 H0.5 Cl1.5), 4(H1.5 O4 P1)'
_chemical_formula_sum            'C229 H355 Cl3 N30 O40 P4'
_chemical_formula_weight         4398.64
_space_group_crystal_system      trigonal
_space_group_IT_number           161
_space_group_name_Hall           'R 3 -2"c'
_space_group_name_H-M_alt        'R 3 c :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-06-27
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   22.0110(7)
_cell_length_b                   22.0110(7)
_cell_length_c                   42.9761(14)
_cell_measurement_reflns_used    9515
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.35
_cell_measurement_theta_min      2.84
_cell_volume                     18031.7(10)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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  0.0611
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       57
_diffrn_reflns_limit_l_min       -57
_diffrn_reflns_number            70836
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.330
_diffrn_reflns_theta_min         1.850
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_T_max  0.4311
_exptl_absorpt_correction_T_min  0.3676
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
 wR2(int) was 0.0647 before and 0.0581 after correction. The Ratio 
 of minimum to maximum transmission is 0.8781. The λ/2 correction
 factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             7110
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 3146 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     474
_refine_ls_number_reflns         9954
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0550
_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)+(0.0960P)²+9.3580P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1422
_refine_ls_wR_factor_ref         0.1612
_reflns_Friedel_coverage         0.993
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                7602
_reflns_number_total             9954
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo8b01481_si_001.cif
_cod_data_source_block           3(TBA3H3P2O8)
_cod_original_cell_volume        18031.7(13)
_cod_original_sg_symbol_H-M      'R 3 c'
_cod_database_code               4035126
_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   0.975
_shelx_estimated_absorpt_t_min   0.955
_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, All O(H) groups
2. Restrained distances
 H6-O7
 1.74 with sigma of 0.01
 H7A-O6
 1.74 with sigma of 0.01
3. Others
 Fixed Sof: Cl1(0.5) H7A(0.5) H6(0.5) C39(0.16667) H39(0.16667)
4.a Ternary CH refined with riding coordinates:
 C39(H39)
4.b Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B), C28(H28A,
 H28B), C29(H29A,H29B), C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B),
 C35(H35A,H35B), C36(H36A,H36B), C37(H37A,H37B)
4.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C3(H3), N3(H3A), C4(H4), N4(H4A), C5(H5), C7(H7), C10(H10),
 C11(H11), C12(H12), C14(H14), C17(H17), C19(H19), C20(H20), C21(H21)
4.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C30(H30A,H30B,
 H30C), C31(H31A,H31B,H31C), C38(H38A,H38B,H38C)
4.e Idealised tetrahedral OH refined as rotating group:
 O7(H7A), O6(H6)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z+1/2'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-y+2/3, -x+1/3, z+5/6'
'-x+y+2/3, y+1/3, z+5/6'
'x+2/3, x-y+1/3, z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-y+1/3, -x+2/3, z+7/6'
'-x+y+1/3, y+2/3, z+7/6'
'x+1/3, x-y+2/3, z+7/6'
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7079(3) 0.5924(3) 0.26381(9) 0.0573(12) Uani 1 1 d . . . . .
H1A H 0.6740 0.5473 0.2546 0.086 Uiso 1 1 calc GR . . . .
H1B H 0.7556 0.6038 0.2582 0.086 Uiso 1 1 calc GR . . . .
H1C H 0.6992 0.6292 0.2560 0.086 Uiso 1 1 calc GR . . . .
N1 N 0.69177(17) 0.47944(17) 0.39427(7) 0.0366(7) Uani 1 1 d . . . . .
H1 H 0.6976 0.4472 0.4037 0.044 Uiso 1 1 calc R . . . .
O1 O 0.70071(19) 0.58817(17) 0.29691(6) 0.0527(8) Uani 1 1 d . . . . .
C2 C 0.7106(2) 0.5389(2) 0.31197(8) 0.0396(8) Uani 1 1 d . . . . .
N2 N 0.66816(17) 0.49982(18) 0.44333(7) 0.0372(7) Uani 1 1 d . . . . .
H2 H 0.6844 0.4716 0.4478 0.045 Uiso 1 1 calc R . . . .
O2 O 0.65665(18) 0.56091(17) 0.40312(6) 0.0480(7) Uani 1 1 d . . . . .
C3 C 0.7295(2) 0.4945(2) 0.29781(9) 0.0447(9) Uani 1 1 d . . . . .
H3 H 0.7377 0.4967 0.2760 0.054 Uiso 1 1 calc R . . . .
N3 N 0.60331(19) 0.45203(18) 0.54827(7) 0.0409(7) Uani 1 1 d . . . . .
H3A H 0.6095 0.4167 0.5434 0.049 Uiso 1 1 calc R . . . .
O3 O 0.57165(18) 0.49673(17) 0.58903(6) 0.0492(7) Uani 1 1 d . . . . .
C4 C 0.7363(2) 0.4464(2) 0.31630(10) 0.0460(10) Uani 1 1 d . . . . .
H4 H 0.7491 0.4154 0.3069 0.055 Uiso 1 1 calc R . . . .
N4 N 0.58693(18) 0.40199(19) 0.59550(7) 0.0429(8) Uani 1 1 d . . . . .
H4A H 0.6031 0.3778 0.5857 0.051 Uiso 1 1 calc R . . . .
O4 O 0.4951(3) 0.4198(3) 0.69674(9) 0.0850(14) Uani 1 1 d . . . . .
C5 C 0.7248(2) 0.4425(2) 0.34801(9) 0.0418(9) Uani 1 1 d . . . . .
H5 H 0.7305 0.4097 0.3602 0.050 Uiso 1 1 calc R . . . .
C6 C 0.70479(19) 0.4874(2) 0.36202(8) 0.0346(7) Uani 1 1 d . . . . .
C7 C 0.6985(2) 0.5355(2) 0.34406(8) 0.0381(8) Uani 1 1 d . . . . .
H7 H 0.6859 0.5667 0.3535 0.046 Uiso 1 1 calc R . . . .
C8 C 0.6708(2) 0.5170(2) 0.41263(8) 0.0357(8) Uani 1 1 d . . . . .
C9 C 0.64307(19) 0.5209(2) 0.46885(8) 0.0333(7) Uani 1 1 d . . . . .
C10 C 0.6301(2) 0.5767(2) 0.46940(8) 0.0407(9) Uani 1 1 d . . . . .
H10 H 0.6351 0.6031 0.4511 0.049 Uiso 1 1 calc R . . . .
C11 C 0.6097(2) 0.5928(2) 0.49739(9) 0.0430(9) Uani 1 1 d . . . . .
H11 H 0.6017 0.6314 0.4980 0.052 Uiso 1 1 calc R . . . .
C12 C 0.6004(2) 0.5543(2) 0.52471(8) 0.0415(9) Uani 1 1 d . . . . .
H12 H 0.5863 0.5664 0.5435 0.050 Uiso 1 1 calc R . . . .
C13 C 0.6123(2) 0.4983(2) 0.52356(8) 0.0369(8) Uani 1 1 d . . . . .
C14 C 0.6335(2) 0.4824(2) 0.49576(8) 0.0344(7) Uani 1 1 d . . . . .
H14 H 0.6418 0.4440 0.4952 0.041 Uiso 1 1 calc R . . . .
C15 C 0.5863(2) 0.4545(2) 0.57880(8) 0.0395(8) Uani 1 1 d . . . . .
C16 C 0.5649(2) 0.3817(2) 0.62657(8) 0.0433(9) Uani 1 1 d . . . . .
C17 C 0.5406(2) 0.4156(3) 0.64563(9) 0.0492(10) Uani 1 1 d . . . . .
H17 H 0.5381 0.4551 0.6384 0.059 Uiso 1 1 calc R . . . .
C18 C 0.5197(3) 0.3901(3) 0.67594(11) 0.0631(14) Uani 1 1 d . . . . .
C19 C 0.5226(4) 0.3330(4) 0.68657(13) 0.082(2) Uani 1 1 d . . . . .
H19 H 0.5081 0.3164 0.7072 0.099 Uiso 1 1 calc R . . . .
C20 C 0.5466(3) 0.2999(4) 0.66733(12) 0.0712(16) Uani 1 1 d . . . . .
H20 H 0.5479 0.2598 0.6746 0.085 Uiso 1 1 calc R . . . .
C21 C 0.5690(3) 0.3241(3) 0.63752(10) 0.0508(10) Uani 1 1 d . . . . .
H21 H 0.5870 0.3018 0.6246 0.061 Uiso 1 1 calc R . . . .
C22 C 0.4962(4) 0.4826(4) 0.68764(13) 0.0811(19) Uani 1 1 d . . . . .
H22A H 0.5439 0.5178 0.6815 0.122 Uiso 1 1 calc GR . . . .
H22B H 0.4812 0.5005 0.7051 0.122 Uiso 1 1 calc GR . . . .
H22C H 0.4642 0.4727 0.6700 0.122 Uiso 1 1 calc GR . . . .
N5 N 0.39252(18) 0.26832(18) 0.50915(8) 0.0411(7) Uani 1 1 d . . . . .
C23 C 0.4415(5) 0.3582(4) 0.39725(13) 0.089(2) Uani 1 1 d . . . . .
H23A H 0.4795 0.3801 0.3820 0.134 Uiso 1 1 calc GR . . . .
H23B H 0.4213 0.3885 0.4007 0.134 Uiso 1 1 calc GR . . . .
H23C H 0.4050 0.3126 0.3894 0.134 Uiso 1 1 calc GR . . . .
C24 C 0.4705(4) 0.3479(4) 0.42808(12) 0.0691(16) Uani 1 1 d . . . . .
H24A H 0.4935 0.3198 0.4243 0.083 Uiso 1 1 calc R . . . .
H24B H 0.5063 0.3942 0.4363 0.083 Uiso 1 1 calc R . . . .
C25 C 0.4120(3) 0.3109(3) 0.45209(10) 0.0517(10) Uani 1 1 d . . . . .
H25A H 0.3909 0.3403 0.4570 0.062 Uiso 1 1 calc R . . . .
H25B H 0.3748 0.2656 0.4436 0.062 Uiso 1 1 calc R . . . .
C26 C 0.4424(2) 0.2980(2) 0.48139(10) 0.0463(9) Uani 1 1 d . . . . .
H26A H 0.4836 0.3430 0.4878 0.056 Uiso 1 1 calc R . . . .
H26B H 0.4594 0.2652 0.4763 0.056 Uiso 1 1 calc R . . . .
C27 C 0.4328(2) 0.2552(2) 0.53435(9) 0.0442(9) Uani 1 1 d . . . . .
H27A H 0.4778 0.2992 0.5376 0.053 Uiso 1 1 calc R . . . .
H27B H 0.4440 0.2196 0.5266 0.053 Uiso 1 1 calc R . . . .
C28 C 0.3969(2) 0.2307(3) 0.56580(9) 0.0469(9) Uani 1 1 d . . . . .
H28A H 0.3467 0.1955 0.5628 0.056 Uiso 1 1 calc R . . . .
H28B H 0.3998 0.2709 0.5774 0.056 Uiso 1 1 calc R . . . .
C29 C 0.4327(3) 0.1984(3) 0.58425(10) 0.0518(10) Uani 1 1 d . . . . .
H29A H 0.4275 0.1569 0.5729 0.062 Uiso 1 1 calc R . . . .
H29B H 0.4835 0.2329 0.5857 0.062 Uiso 1 1 calc R . . . .
C30 C 0.4031(3) 0.1763(3) 0.61683(11) 0.0642(13) Uani 1 1 d . . . . .
H30A H 0.3519 0.1480 0.6158 0.096 Uiso 1 1 calc GR . . . .
H30B H 0.4166 0.2181 0.6296 0.096 Uiso 1 1 calc GR . . . .
H30C H 0.4218 0.1484 0.6262 0.096 Uiso 1 1 calc GR . . . .
C31 C 0.3843(4) 0.4207(4) 0.5743(2) 0.103(3) Uani 1 1 d . . . . .
H31A H 0.3487 0.3709 0.5759 0.154 Uiso 1 1 calc GR . . . .
H31B H 0.3655 0.4493 0.5827 0.154 Uiso 1 1 calc GR . . . .
H31C H 0.4261 0.4297 0.5861 0.154 Uiso 1 1 calc GR . . . .
C32 C 0.4035(4) 0.4393(3) 0.54095(18) 0.0808(18) Uani 1 1 d . . . . .
H32A H 0.4403 0.4893 0.5395 0.097 Uiso 1 1 calc R . . . .
H32B H 0.3619 0.4331 0.5294 0.097 Uiso 1 1 calc R . . . .
C33 C 0.4299(3) 0.3945(3) 0.52618(13) 0.0615(12) Uani 1 1 d . . . . .
H33A H 0.4646 0.3925 0.5402 0.074 Uiso 1 1 calc R . . . .
H33B H 0.4538 0.4163 0.5064 0.074 Uiso 1 1 calc R . . . .
C34 C 0.3701(2) 0.3200(2) 0.51980(11) 0.0481(10) Uani 1 1 d . . . . .
H34A H 0.3420 0.3016 0.5390 0.058 Uiso 1 1 calc R . . . .
H34B H 0.3392 0.3222 0.5037 0.058 Uiso 1 1 calc R . . . .
C35 C 0.3260(2) 0.2015(2) 0.50069(9) 0.0422(9) Uani 1 1 d . . . . .
H35A H 0.3015 0.2125 0.4842 0.051 Uiso 1 1 calc R . . . .
H35B H 0.2950 0.1854 0.5192 0.051 Uiso 1 1 calc R . . . .
C36 C 0.3356(3) 0.1411(2) 0.48939(11) 0.0523(10) Uani 1 1 d . . . . .
H36A H 0.3516 0.1233 0.5069 0.063 Uiso 1 1 calc R . . . .
H36B H 0.3719 0.1581 0.4729 0.063 Uiso 1 1 calc R . . . .
C37 C 0.2665(3) 0.0822(3) 0.47661(12) 0.0603(12) Uani 1 1 d . . . . .
H37A H 0.2699 0.0392 0.4746 0.072 Uiso 1 1 calc R . . . .
H37B H 0.2286 0.0723 0.4917 0.072 Uiso 1 1 calc R . . . .
C38 C 0.2470(4) 0.0987(3) 0.44565(13) 0.084(2) Uani 1 1 d . . . . .
H38A H 0.2847 0.1095 0.4307 0.127 Uiso 1 1 calc GR . . . .
H38B H 0.2402 0.1392 0.4477 0.127 Uiso 1 1 calc GR . . . .
H38C H 0.2034 0.0581 0.4383 0.127 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.64694(17) 0.39731(16) 0.73564(6) 0.0691(7) Uani 0.5 1 d . . . . .
P2 P 0.6667 0.3333 0.53579(4) 0.0385(4) Uani 1 3 d S T P . .
O7 O 0.59827(15) 0.32783(15) 0.52279(6) 0.0401(6) Uani 1 1 d D . . . .
H7A H 0.5955 0.3196 0.5036 0.060 Uiso 0.5 1 calc DGR . . A 1
O8 O 0.6667 0.3333 0.57049(11) 0.0449(11) Uani 1 3 d S T P . .
P1 P 0.6667 0.3333 0.45021(4) 0.0339(3) Uani 1 3 d S T P . .
O5 O 0.6667 0.3333 0.41562(10) 0.0401(11) Uani 1 3 d S T P . .
O6 O 0.59250(14) 0.31122(14) 0.46326(6) 0.0384(6) Uani 1 1 d D . . . .
H6 H 0.5935 0.3108 0.4828 0.058 Uiso 0.5 1 calc DGR . . B 2
C39 C 0.6667 0.3333 0.7230(4) 0.068(5) Uani 0.5 3 d S T P . .
H39 H 0.6667 0.3333 0.6997 0.082 Uiso 0.5 3 calc RS T P . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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
H1A C1 H1B 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
O1 C1 H1A 109.5 . .
O1 C1 H1B 109.5 . .
O1 C1 H1C 109.5 . .
C6 N1 H1 116.7 . .
C8 N1 H1 116.7 . .
C8 N1 C6 126.6(3) . .
C2 O1 C1 117.8(3) . .
O1 C2 C3 125.1(3) . .
O1 C2 C7 114.0(3) . .
C3 C2 C7 120.8(4) . .
C8 N2 H2 115.4 . .
C8 N2 C9 129.1(3) . .
C9 N2 H2 115.4 . .
C2 C3 H3 120.9 . .
C2 C3 C4 118.2(3) . .
C4 C3 H3 120.9 . .
C13 N3 H3A 115.5 . .
C15 N3 H3A 115.5 . .
C15 N3 C13 129.1(4) . .
C3 C4 H4 119.1 . .
C5 C4 C3 121.8(4) . .
C5 C4 H4 119.1 . .
C15 N4 H4A 116.0 . .
C15 N4 C16 128.0(4) . .
C16 N4 H4A 116.0 . .
C18 O4 C22 117.7(4) . .
C4 C5 H5 120.3 . .
C4 C5 C6 119.4(4) . .
C6 C5 H5 120.3 . .
C5 C6 N1 116.8(3) . .
C7 C6 N1 123.8(3) . .
C7 C6 C5 119.4(3) . .
C2 C7 H7 119.8 . .
C6 C7 C2 120.4(4) . .
C6 C7 H7 119.8 . .
N2 C8 N1 111.5(3) . .
O2 C8 N1 125.2(3) . .
O2 C8 N2 123.3(3) . .
C10 C9 N2 126.2(3) . .
C14 C9 N2 114.4(3) . .
C14 C9 C10 119.3(3) . .
C9 C10 H10 120.9 . .
C11 C10 C9 118.3(3) . .
C11 C10 H10 120.9 . .
C10 C11 H11 118.7 . .
C10 C11 C12 122.6(4) . .
C12 C11 H11 118.7 . .
C11 C12 H12 120.9 . .
C13 C12 C11 118.2(3) . .
C13 C12 H12 120.9 . .
C12 C13 N3 126.5(3) . .
C12 C13 C14 119.5(3) . .
C14 C13 N3 114.0(3) . .
C9 C14 C13 122.0(4) . .
C9 C14 H14 119.0 . .
C13 C14 H14 119.0 . .
O3 C15 N3 124.2(4) . .
O3 C15 N4 125.4(3) . .
N4 C15 N3 110.4(3) . .
C17 C16 N4 123.5(4) . .
C17 C16 C21 120.5(4) . .
C21 C16 N4 116.0(4) . .
C16 C17 H17 121.0 . .
C16 C17 C18 118.1(5) . .
C18 C17 H17 121.0 . .
O4 C18 C17 122.9(5) . .
C19 C18 O4 115.6(4) . .
C19 C18 C17 121.5(5) . .
C18 C19 H19 120.2 . .
C18 C19 C20 119.6(5) . .
C20 C19 H19 120.2 . .
C19 C20 H20 119.6 . .
C19 C20 C21 120.7(5) . .
C21 C20 H20 119.6 . .
C16 C21 H21 120.2 . .
C20 C21 C16 119.5(4) . .
C20 C21 H21 120.2 . .
O4 C22 H22A 109.5 . .
O4 C22 H22B 109.5 . .
O4 C22 H22C 109.5 . .
H22A C22 H22B 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
C27 N5 C26 106.0(3) . .
C27 N5 C34 111.5(3) . .
C34 N5 C26 110.3(3) . .
C35 N5 C26 111.5(3) . .
C35 N5 C27 111.1(3) . .
C35 N5 C34 106.4(3) . .
H23A C23 H23B 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
C24 C23 H23A 109.5 . .
C24 C23 H23B 109.5 . .
C24 C23 H23C 109.5 . .
C23 C24 H24A 109.4 . .
C23 C24 H24B 109.4 . .
H24A C24 H24B 108.0 . .
C25 C24 C23 111.0(5) . .
C25 C24 H24A 109.4 . .
C25 C24 H24B 109.4 . .
C24 C25 H25A 109.9 . .
C24 C25 H25B 109.9 . .
H25A C25 H25B 108.3 . .
C26 C25 C24 109.1(4) . .
C26 C25 H25A 109.9 . .
C26 C25 H25B 109.9 . .
N5 C26 H26A 108.3 . .
N5 C26 H26B 108.3 . .
C25 C26 N5 116.0(4) . .
C25 C26 H26A 108.3 . .
C25 C26 H26B 108.3 . .
H26A C26 H26B 107.4 . .
N5 C27 H27A 108.1 . .
N5 C27 H27B 108.1 . .
N5 C27 C28 116.9(3) . .
H27A C27 H27B 107.3 . .
C28 C27 H27A 108.1 . .
C28 C27 H27B 108.1 . .
C27 C28 H28A 109.8 . .
C27 C28 H28B 109.8 . .
C27 C28 C29 109.3(3) . .
H28A C28 H28B 108.3 . .
C29 C28 H28A 109.8 . .
C29 C28 H28B 109.8 . .
C28 C29 H29A 109.0 . .
C28 C29 H29B 109.0 . .
H29A C29 H29B 107.8 . .
C30 C29 C28 113.0(4) . .
C30 C29 H29A 109.0 . .
C30 C29 H29B 109.0 . .
C29 C30 H30A 109.5 . .
C29 C30 H30B 109.5 . .
C29 C30 H30C 109.5 . .
H30A C30 H30B 109.5 . .
H30A C30 H30C 109.5 . .
H30B C30 H30C 109.5 . .
H31A C31 H31B 109.5 . .
H31A C31 H31C 109.5 . .
H31B C31 H31C 109.5 . .
C32 C31 H31A 109.5 . .
C32 C31 H31B 109.5 . .
C32 C31 H31C 109.5 . .
C31 C32 H32A 109.2 . .
C31 C32 H32B 109.2 . .
C31 C32 C33 111.9(6) . .
H32A C32 H32B 107.9 . .
C33 C32 H32A 109.2 . .
C33 C32 H32B 109.2 . .
C32 C33 H33A 109.3 . .
C32 C33 H33B 109.3 . .
C32 C33 C34 111.7(5) . .
H33A C33 H33B 107.9 . .
C34 C33 H33A 109.3 . .
C34 C33 H33B 109.3 . .
N5 C34 C33 115.5(4) . .
N5 C34 H34A 108.4 . .
N5 C34 H34B 108.4 . .
C33 C34 H34A 108.4 . .
C33 C34 H34B 108.4 . .
H34A C34 H34B 107.5 . .
N5 C35 H35A 108.3 . .
N5 C35 H35B 108.3 . .
N5 C35 C36 115.8(4) . .
H35A C35 H35B 107.4 . .
C36 C35 H35A 108.3 . .
C36 C35 H35B 108.3 . .
C35 C36 H36A 109.7 . .
C35 C36 H36B 109.7 . .
C35 C36 C37 110.0(4) . .
H36A C36 H36B 108.2 . .
C37 C36 H36A 109.7 . .
C37 C36 H36B 109.7 . .
C36 C37 H37A 108.9 . .
C36 C37 H37B 108.9 . .
H37A C37 H37B 107.7 . .
C38 C37 C36 113.5(5) . .
C38 C37 H37A 108.9 . .
C38 C37 H37B 108.9 . .
C37 C38 H38A 109.5 . .
C37 C38 H38B 109.5 . .
C37 C38 H38C 109.5 . .
H38A C38 H38B 109.5 . .
H38A C38 H38C 109.5 . .
H38B C38 H38C 109.5 . .
O7 P2 O7 107.80(11) 2_655 .
O7 P2 O7 107.80(11) 3_665 .
O7 P2 O7 107.80(11) 2_655 3_665
O8 P2 O7 111.09(10) . 2_655
O8 P2 O7 111.09(11) . 3_665
O8 P2 O7 111.09(11) . .
P2 O7 H7A 109.5 . .
O5 P1 O6 111.11(11) . .
O5 P1 O6 111.11(11) . 3_665
O5 P1 O6 111.11(11) . 2_655
O6 P1 O6 107.78(11) 2_655 .
O6 P1 O6 107.78(11) 3_665 .
O6 P1 O6 107.78(11) 2_655 3_665
P1 O6 H6 109.5 . .
Cl1 C39 Cl1 110.9(5) 3_665 .
Cl1 C39 Cl1 110.9(5) 2_655 .
Cl1 C39 Cl1 110.9(5) 3_665 2_655
Cl1 C39 H39 108.0 3_665 .
Cl1 C39 H39 108.0 2_655 .
Cl1 C39 H39 108.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
C1 O1 1.429(4) .
N1 H1 0.8800 .
N1 C6 1.408(4) .
N1 C8 1.379(5) .
O1 C2 1.370(5) .
C2 C3 1.382(6) .
C2 C7 1.399(5) .
N2 H2 0.8800 .
N2 C8 1.366(4) .
N2 C9 1.407(5) .
O2 C8 1.224(5) .
C3 H3 0.9500 .
C3 C4 1.390(7) .
N3 H3A 0.8800 .
N3 C13 1.415(5) .
N3 C15 1.373(5) .
O3 C15 1.208(5) .
C4 H4 0.9500 .
C4 C5 1.381(6) .
N4 H4A 0.8800 .
N4 C15 1.367(6) .
N4 C16 1.415(5) .
O4 C18 1.370(6) .
O4 C22 1.425(7) .
C5 H5 0.9500 .
C5 C6 1.404(5) .
C6 C7 1.372(5) .
C7 H7 0.9500 .
C9 C10 1.394(6) .
C9 C14 1.386(5) .
C10 H10 0.9500 .
C10 C11 1.390(5) .
C11 H11 0.9500 .
C11 C12 1.402(6) .
C12 H12 0.9500 .
C12 C13 1.384(6) .
C13 C14 1.390(5) .
C14 H14 0.9500 .
C16 C17 1.384(6) .
C16 C21 1.395(7) .
C17 H17 0.9500 .
C17 C18 1.402(6) .
C18 C19 1.368(8) .
C19 H19 0.9500 .
C19 C20 1.371(8) .
C20 H20 0.9500 .
C20 C21 1.380(6) .
C21 H21 0.9500 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
N5 C26 1.529(5) .
N5 C27 1.516(5) .
N5 C34 1.519(6) .
N5 C35 1.512(5) .
C23 H23A 0.9800 .
C23 H23B 0.9800 .
C23 H23C 0.9800 .
C23 C24 1.536(8) .
C24 H24A 0.9900 .
C24 H24B 0.9900 .
C24 C25 1.529(7) .
C25 H25A 0.9900 .
C25 H25B 0.9900 .
C25 C26 1.517(6) .
C26 H26A 0.9900 .
C26 H26B 0.9900 .
C27 H27A 0.9900 .
C27 H27B 0.9900 .
C27 C28 1.522(5) .
C28 H28A 0.9900 .
C28 H28B 0.9900 .
C28 C29 1.522(6) .
C29 H29A 0.9900 .
C29 H29B 0.9900 .
C29 C30 1.518(6) .
C30 H30A 0.9800 .
C30 H30B 0.9800 .
C30 H30C 0.9800 .
C31 H31A 0.9800 .
C31 H31B 0.9800 .
C31 H31C 0.9800 .
C31 C32 1.491(11) .
C32 H32A 0.9900 .
C32 H32B 0.9900 .
C32 C33 1.510(9) .
C33 H33A 0.9900 .
C33 H33B 0.9900 .
C33 C34 1.529(7) .
C34 H34A 0.9900 .
C34 H34B 0.9900 .
C35 H35A 0.9900 .
C35 H35B 0.9900 .
C35 C36 1.525(6) .
C36 H36A 0.9900 .
C36 H36B 0.9900 .
C36 C37 1.526(7) .
C37 H37A 0.9900 .
C37 H37B 0.9900 .
C37 C38 1.497(8) .
C38 H38A 0.9800 .
C38 H38B 0.9800 .
C38 H38C 0.9800 .
Cl1 C39 1.754(6) .
P2 O7 1.553(3) .
P2 O7 1.553(3) 2_655
P2 O7 1.553(3) 3_665
P2 O8 1.491(5) .
O7 H7A 0.8400 .
P1 O5 1.487(4) .
P1 O6 1.556(3) 2_655
P1 O6 1.556(3) 3_665
P1 O6 1.556(3) .
O6 H6 0.8400 .
C39 Cl1 1.754(6) 3_665
C39 Cl1 1.754(6) 2_655
C39 H39 1.0000 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O5 0.88 2.30 3.116(3) 153.8 .
N2 H2 O6 0.88 2.02 2.892(4) 173.2 3_665
N3 H3A O7 0.88 2.05 2.895(4) 161.9 .
N4 H4A O8 0.88 2.17 3.029(4) 164.2 .
C7 H7 O2 0.95 2.21 2.849(4) 123.4 .
C17 H17 O3 0.95 2.28 2.890(5) 121.1 .
O7 H7A O6 0.84 1.74 2.579(3) 174.3 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C1 O1 C2 C3 2.4(6)
C1 O1 C2 C7 -176.4(4)
N1 C6 C7 C2 -178.3(4)
O1 C2 C3 C4 -178.9(4)
O1 C2 C7 C6 178.4(4)
C2 C3 C4 C5 -0.2(7)
N2 C9 C10 C11 -175.8(4)
N2 C9 C14 C13 176.8(3)
C3 C2 C7 C6 -0.5(6)
C3 C4 C5 C6 1.0(7)
N3 C13 C14 C9 178.2(3)
C4 C5 C6 N1 178.1(4)
C4 C5 C6 C7 -1.5(6)
N4 C16 C17 C18 179.5(5)
N4 C16 C21 C20 -178.3(5)
O4 C18 C19 C20 -180.0(6)
C5 C6 C7 C2 1.3(6)
C6 N1 C8 N2 -175.3(4)
C6 N1 C8 O2 4.2(7)
C7 C2 C3 C4 0.0(6)
C8 N1 C6 C5 -179.2(4)
C8 N1 C6 C7 0.4(6)
C8 N2 C9 C10 -15.8(7)
C8 N2 C9 C14 166.6(4)
C9 N2 C8 N1 -173.2(4)
C9 N2 C8 O2 7.3(7)
C9 C10 C11 C12 -1.3(6)
C10 C9 C14 C13 -0.9(6)
C10 C11 C12 C13 0.2(6)
C11 C12 C13 N3 -177.6(4)
C11 C12 C13 C14 0.6(6)
C12 C13 C14 C9 -0.2(6)
C13 N3 C15 O3 4.8(7)
C13 N3 C15 N4 -176.3(4)
C14 C9 C10 C11 1.6(6)
C15 N3 C13 C12 -5.2(7)
C15 N3 C13 C14 176.5(4)
C15 N4 C16 C17 -2.4(7)
C15 N4 C16 C21 177.7(4)
C16 N4 C15 N3 -172.2(4)
C16 N4 C15 O3 6.6(7)
C16 C17 C18 O4 179.8(5)
C16 C17 C18 C19 -0.4(9)
C17 C16 C21 C20 1.8(7)
C17 C18 C19 C20 0.1(11)
C18 C19 C20 C21 1.1(11)
C19 C20 C21 C16 -2.1(9)
C21 C16 C17 C18 -0.6(7)
C22 O4 C18 C17 -5.0(9)
C22 O4 C18 C19 175.2(7)
N5 C27 C28 C29 162.0(4)
N5 C35 C36 C37 -170.5(3)
C23 C24 C25 C26 176.7(5)
C24 C25 C26 N5 173.7(4)
C26 N5 C27 C28 175.3(4)
C26 N5 C34 C33 -52.4(5)
C26 N5 C35 C36 60.0(4)
C27 N5 C26 C25 175.9(4)
C27 N5 C34 C33 65.1(5)
C27 N5 C35 C36 -58.0(4)
C27 C28 C29 C30 176.6(4)
C31 C32 C33 C34 74.3(7)
C32 C33 C34 N5 -171.8(5)
C34 N5 C26 C25 -63.2(5)
C34 N5 C27 C28 55.2(5)
C34 N5 C35 C36 -179.6(3)
C35 N5 C26 C25 54.8(5)
C35 N5 C27 C28 -63.4(5)
C35 N5 C34 C33 -173.5(4)
C35 C36 C37 C38 73.4(6)
