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#$Date: 2024-09-06 03:20:52 +0300 (Fri, 06 Sep 2024) $
#$Revision: 294533 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/89/7248993.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_7248993
loop_
_publ_author_name
'Ochsenbein, Philippe'
'Bonin, Michel'
'Fadaei-Tirani, Farzaneh'
'Lemée, Marie-Hélène'
'Kieffer, Jérôme'
'Görl, Daniel'
'El-Hajji, Mohamed'
'Schenk-Joß, Kurt'
_publ_section_title
;
 A score and nine years of irbesartan
;
_journal_issue                   34
_journal_name_full               CrystEngComm
_journal_page_first              4566
_journal_page_last               4578
_journal_paper_doi               10.1039/D3CE01172K
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C25 H28 N6 O, 0.4[H2O]'
_chemical_formula_sum            'C25 H28 N6 O'
_chemical_formula_weight         428.53
_chemical_name_common            SR47436-A
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-04-27
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-04-27 deposited with the CCDC.	2024-05-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   37.3328(5)
_cell_length_b                   37.3328(5)
_cell_length_c                   9.7877(2)
_cell_measurement_reflns_used    9915
_cell_measurement_temperature    231(1)
_cell_measurement_theta_max      54.19
_cell_measurement_theta_min      2.37
_cell_volume                     11813.9(3)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker Instrument Service v2016.5.0.1'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      231(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX_DUO'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            38412
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        54.811
_diffrn_reflns_theta_max         54.811
_diffrn_reflns_theta_min         2.367
_diffrn_source                   'Incoatec microsource'
_exptl_absorpt_coefficient_mu    0.550
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6474
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS V2012/1 (Bruker AXS Inc.) was used for absorption correction.
wR2(int) was 0.1579 before and 0.0469 after correction.
The Ratio of minimum to maximum transmission is 0.867.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.084
_exptl_crystal_description       prism
_exptl_crystal_F_000             4104
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.016
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.000037(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         3273
_refine_ls_number_restraints     75
_refine_ls_restrained_S_all      1.198
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0543P)²+9.9024P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1021
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2874
_reflns_number_total             3273
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce01172k2.cif
_cod_data_source_block           ibs_a_231k_zwitter
_cod_depositor_comments
'Adding full bibliography for 7248992--7248997.cif.'
_cod_original_cell_volume        11813.9(4)
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               7248993
_shelx_shelxl_version_number     2018/3
_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   0.991
_shelx_estimated_absorpt_t_min   0.771
_exptl_absorpt_special_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C2T1-C1 \\sim C2T2-C1 \\sim C2T1-C3T1 \\sim C2T2-C3T2 \\sim C4T1-C3T1 \\sim
C4T2-C3T2
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C1 \\sim C2T1 \\sim C2T2 \\sim C3T1 \\sim C3T2 \\sim C4T1 \\sim C4T2: within 2A
with sigma of 0.005 and sigma for terminal atoms of 0.01 within 2A
4. Others
 Sof(H1BC)=Sof(H1BD)=Sof(C2T2)=Sof(H2TC)=Sof(H2TD)=Sof(C3T2)=Sof(H3TC)=
 Sof(H3TD)=Sof(C4T2)=Sof(H4TD)=Sof(H4TE)=Sof(H4TF)=1-FVAR(1)
 Sof(H1AA)=Sof(H1AB)=Sof(C2T1)=Sof(H2TA)=Sof(H2TB)=Sof(C3T1)=Sof(H3TA)=
 Sof(H3TB)=Sof(C4T1)=Sof(H4TA)=Sof(H4TB)=Sof(H4TC)=FVAR(1)
 Sof(H1N)=1-FVAR(2)
 Sof(H1)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C1(H1AA,H1AB), C1(H1BC,H1BD), C1M(H1MA,H1MB), C2T1(H2TA,H2TB), C2T2(H2TC,
 H2TD), C3T1(H3TA,H3TB), C3T2(H3TC,H3TD), C6N(H6NA,H6NB), C7N(H7NA,H7NB),
 C8N(H8NA,H8NB), C9N(H9NA,H9NB)
5.b Aromatic/amide H refined with riding coordinates:
 C2B(H2B), C3B(H3B), C3P(H3P), C4P(H4P), C5B(H5B), C5P(H5P), C6B(H6B), C6P(H6P)
5.c Idealised Me refined as rotating group:
 C4T1(H4TA,H4TB,H4TC), C4T2(H4TD,H4TE,H4TF)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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'
'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'
'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'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-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'
'-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'
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
O1N O 0.39161(4) 0.42018(4) 0.52002(14) 0.0602(4) Uani 1 1 d . . . . .
N1 N 0.15049(4) 0.24210(4) 0.32052(16) 0.0414(4) Uani 1 1 d . . . . .
H1 H 0.1632(7) 0.2428(6) 0.401(3) 0.037(8) Uiso 0.79(4) 1 d . . P A 1
N1N N 0.39540(5) 0.48245(5) 0.24234(16) 0.0443(4) Uani 1 1 d . . . . .
H1N H 0.403(3) 0.496(3) 0.179(12) 0.053 Uiso 0.21(4) 1 d . U P A 2
N2 N 0.11838(5) 0.24895(5) 0.31734(16) 0.0498(4) Uani 1 1 d . . . . .
N3 N 0.10513(5) 0.24263(5) 0.19277(16) 0.0551(4) Uani 1 1 d . . . . .
N3N N 0.34956(4) 0.43347(4) 0.38209(13) 0.0372(4) Uani 1 1 d . . . . .
N4 N 0.12783(5) 0.23156(5) 0.11376(15) 0.0513(4) Uani 1 1 d . . . . .
C1 C 0.32312(6) 0.46342(7) 0.2052(2) 0.0600(5) Uani 1 1 d D U . . .
H1AA H 0.297102 0.437122 0.213586 0.072 Uiso 0.555(4) 1 calc R U P B 1
H1AB H 0.329372 0.469318 0.107755 0.072 Uiso 0.555(4) 1 calc R U P B 1
H1BC H 0.315094 0.445665 0.124069 0.072 Uiso 0.445(4) 1 calc R U P B 2
H1BD H 0.299349 0.451201 0.267280 0.072 Uiso 0.445(4) 1 calc R U P B 2
C1B C 0.24925(5) 0.28224(5) 0.24891(16) 0.0345(4) Uani 1 1 d . . . . .
C1M C 0.30975(5) 0.40266(5) 0.44109(18) 0.0433(5) Uani 1 1 d . . . . .
H1MA H 0.290735 0.413573 0.437953 0.052 Uiso 1 1 calc R U . . .
H1MB H 0.313989 0.398518 0.537320 0.052 Uiso 1 1 calc R U . . .
C1P C 0.22821(5) 0.24044(5) 0.18576(16) 0.0360(4) Uani 1 1 d . . . . .
C2B C 0.27957(5) 0.29258(5) 0.34821(17) 0.0410(4) Uani 1 1 d . . . . .
H2B H 0.286558 0.272727 0.375815 0.049 Uiso 1 1 calc R U . . .
C2N C 0.35700(6) 0.46017(5) 0.27331(17) 0.0409(4) Uani 1 1 d . . . . .
C2P C 0.18572(5) 0.21837(5) 0.15517(16) 0.0397(4) Uani 1 1 d . . . . .
C2T1 C 0.31866(14) 0.49734(14) 0.2701(5) 0.0783(12) Uani 0.555(4) 1 d D U P B 1
H2TA H 0.346051 0.522127 0.277243 0.094 Uiso 0.555(4) 1 calc R U P B 1
H2TB H 0.307883 0.488917 0.363006 0.094 Uiso 0.555(4) 1 calc R U P B 1
C2T2 C 0.32880(17) 0.50317(15) 0.1617(7) 0.0778(13) Uani 0.445(4) 1 d D U P B 2
H2TC H 0.351887 0.515504 0.096903 0.093 Uiso 0.445(4) 1 calc R U P B 2
H2TD H 0.336777 0.521401 0.241557 0.093 Uiso 0.445(4) 1 calc R U P B 2
C3B C 0.29957(5) 0.33136(6) 0.40694(17) 0.0419(5) Uani 1 1 d . . . . .
H3B H 0.320062 0.337553 0.473301 0.050 Uiso 1 1 calc R U . . .
C3P C 0.16902(6) 0.18053(6) 0.08815(19) 0.0539(5) Uani 1 1 d . . . . .
H3P H 0.140772 0.166322 0.065485 0.065 Uiso 1 1 calc R U . . .
C3T1 C 0.29056(18) 0.50798(18) 0.1928(7) 0.1027(14) Uani 0.555(4) 1 d D U P B 1
H3TA H 0.303680 0.521004 0.106004 0.123 Uiso 0.555(4) 1 calc R U P B 1
H3TB H 0.264729 0.482463 0.171928 0.123 Uiso 0.555(4) 1 calc R U P B 1
C3T2 C 0.2918(2) 0.5022(2) 0.0958(9) 0.0967(17) Uani 0.445(4) 1 d D U P B 2
H3TC H 0.282773 0.482944 0.018591 0.116 Uiso 0.445(4) 1 calc R U P B 2
H3TD H 0.269139 0.491633 0.162161 0.116 Uiso 0.445(4) 1 calc R U P B 2
C4B C 0.28986(5) 0.36135(5) 0.36940(16) 0.0360(4) Uani 1 1 d . . . . .
C4N C 0.38686(5) 0.43891(5) 0.42720(18) 0.0411(4) Uani 1 1 d . . . . .
C4P C 0.19322(7) 0.16348(6) 0.0543(2) 0.0587(6) Uani 1 1 d . . . . .
H4P H 0.181527 0.137891 0.008936 0.070 Uiso 1 1 calc R U . . .
C4T1 C 0.2810(3) 0.5358(2) 0.2686(10) 0.183(3) Uani 0.555(4) 1 d D U P B 1
H4TA H 0.265947 0.544694 0.210161 0.275 Uiso 0.555(4) 1 calc R U P B 1
H4TB H 0.306554 0.559780 0.298492 0.275 Uiso 0.555(4) 1 calc R U P B 1
H4TC H 0.264266 0.521519 0.347647 0.275 Uiso 0.555(4) 1 calc R U P B 1
C4T2 C 0.2998(3) 0.5427(2) 0.0468(10) 0.150(3) Uani 0.445(4) 1 d D U P B 2
H4TD H 0.320623 0.552393 -0.024585 0.225 Uiso 0.445(4) 1 calc R U P B 2
H4TE H 0.309702 0.562264 0.121940 0.225 Uiso 0.445(4) 1 calc R U P B 2
H4TF H 0.274486 0.540189 0.010725 0.225 Uiso 0.445(4) 1 calc R U P B 2
C5 C 0.15607(5) 0.23162(5) 0.19522(17) 0.0384(4) Uani 1 1 d . . . . .
C5B C 0.26008(5) 0.35138(5) 0.26904(17) 0.0389(4) Uani 1 1 d . . . . .
H5B H 0.253102 0.371260 0.241717 0.047 Uiso 1 1 calc R U . . .
C5N C 0.41930(5) 0.47252(5) 0.33894(16) 0.0389(4) Uani 1 1 d . . . . .
C5P C 0.23425(6) 0.18406(6) 0.08732(19) 0.0509(5) Uani 1 1 d . . . . .
H5P H 0.250701 0.172261 0.066496 0.061 Uiso 1 1 calc R U . . .
C6B C 0.24051(5) 0.31282(5) 0.20860(17) 0.0377(4) Uani 1 1 d . . . . .
H6B H 0.220977 0.307113 0.139164 0.045 Uiso 1 1 calc R U . . .
C6N C 0.44973(6) 0.51099(6) 0.41994(19) 0.0503(5) Uani 1 1 d . . . . .
H6NA H 0.437668 0.528439 0.440347 0.060 Uiso 1 1 calc R U . . .
H6NB H 0.457484 0.503199 0.505899 0.060 Uiso 1 1 calc R U . . .
C6P C 0.25169(6) 0.22206(6) 0.15099(17) 0.0427(5) Uani 1 1 d . . . . .
H6P H 0.280091 0.235972 0.171554 0.051 Uiso 1 1 calc R U . . .
C7N C 0.48682(6) 0.53323(6) 0.3264(2) 0.0563(5) Uani 1 1 d . . . . .
H7NA H 0.483335 0.551970 0.264858 0.068 Uiso 1 1 calc R U . . .
H7NB H 0.512154 0.549356 0.379777 0.068 Uiso 1 1 calc R U . . .
C8N C 0.48897(6) 0.49977(6) 0.2461(2) 0.0520(5) Uani 1 1 d . . . . .
H8NA H 0.511717 0.496150 0.279421 0.062 Uiso 1 1 calc R U . . .
H8NB H 0.493533 0.507062 0.148964 0.062 Uiso 1 1 calc R U . . .
C9N C 0.44778(6) 0.46029(6) 0.2666(2) 0.0545(5) Uani 1 1 d . . . . .
H9NA H 0.451481 0.440567 0.322336 0.065 Uiso 1 1 calc R U . . .
H9NB H 0.436005 0.447389 0.178312 0.065 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 H1 120.8(13) . . ?
C5 N1 H1 130.4(13) . . ?
C5 N1 N2 108.59(15) . . ?
C2N N1N H1N 123(7) . . ?
C2N N1N C5N 107.88(15) . . ?
C5N N1N H1N 129(7) . . ?
N3 N2 N1 106.46(14) . . ?
N2 N3 N4 110.69(14) . . ?
C2N N3N C1M 128.69(14) . . ?
C4N N3N C1M 122.87(14) . . ?
C4N N3N C2N 108.40(14) . . ?
C5 N4 N3 105.97(14) . . ?
H1AA C1 H1AB 108.2 . . ?
H1BC C1 H1BD 106.8 . . ?
C2N C1 H1AA 109.7 . . ?
C2N C1 H1AB 109.7 . . ?
C2N C1 H1BC 107.0 . . ?
C2N C1 H1BD 107.0 . . ?
C2N C1 C2T1 109.7(2) . . ?
C2T1 C1 H1AA 109.7 . . ?
C2T1 C1 H1AB 109.7 . . ?
C2T2 C1 H1BC 107.0 . . ?
C2T2 C1 H1BD 107.0 . . ?
C2T2 C1 C2N 121.2(3) . . ?
C2B C1B C1P 120.74(14) . . ?
C2B C1B C6B 117.51(15) . . ?
C6B C1B C1P 121.71(15) . . ?
N3N C1M H1MA 108.8 . . ?
N3N C1M H1MB 108.8 . . ?
N3N C1M C4B 113.96(13) . . ?
H1MA C1M H1MB 107.7 . . ?
C4B C1M H1MA 108.8 . . ?
C4B C1M H1MB 108.8 . . ?
C2P C1P C1B 123.56(14) . . ?
C6P C1P C1B 118.97(15) . . ?
C6P C1P C2P 117.45(16) . . ?
C1B C2B H2B 119.3 . . ?
C3B C2B C1B 121.36(16) . . ?
C3B C2B H2B 119.3 . . ?
N1N C2N N3N 113.86(16) . . ?
N1N C2N C1 124.12(16) . . ?
N3N C2N C1 121.96(16) . . ?
C1P C2P C5 124.29(15) . . ?
C3P C2P C1P 119.79(16) . . ?
C3P C2P C5 115.86(16) . . ?
C1 C2T1 H2TA 108.9 . . ?
C1 C2T1 H2TB 108.9 . . ?
C1 C2T1 C3T1 113.4(4) . . ?
H2TA C2T1 H2TB 107.7 . . ?
C3T1 C2T1 H2TA 108.9 . . ?
C3T1 C2T1 H2TB 108.9 . . ?
C1 C2T2 H2TC 108.3 . . ?
C1 C2T2 H2TD 108.3 . . ?
C1 C2T2 C3T2 115.9(4) . . ?
H2TC C2T2 H2TD 107.4 . . ?
C3T2 C2T2 H2TC 108.3 . . ?
C3T2 C2T2 H2TD 108.3 . . ?
C2B C3B H3B 119.5 . . ?
C2B C3B C4B 120.91(16) . . ?
C4B C3B H3B 119.5 . . ?
C2P C3P H3P 119.4 . . ?
C4P C3P C2P 121.15(18) . . ?
C4P C3P H3P 119.4 . . ?
C2T1 C3T1 H3TA 109.1 . . ?
C2T1 C3T1 H3TB 109.1 . . ?
H3TA C3T1 H3TB 107.8 . . ?
C4T1 C3T1 C2T1 112.6(6) . . ?
C4T1 C3T1 H3TA 109.1 . . ?
C4T1 C3T1 H3TB 109.1 . . ?
C2T2 C3T2 H3TC 108.8 . . ?
C2T2 C3T2 H3TD 108.8 . . ?
H3TC C3T2 H3TD 107.7 . . ?
C4T2 C3T2 C2T2 113.8(6) . . ?
C4T2 C3T2 H3TC 108.8 . . ?
C4T2 C3T2 H3TD 108.8 . . ?
C3B C4B C1M 120.51(15) . . ?
C5B C4B C1M 121.49(15) . . ?
C5B C4B C3B 117.93(16) . . ?
O1N C4N N3N 125.78(16) . . ?
O1N C4N C5N 128.44(16) . . ?
N3N C4N C5N 105.78(14) . . ?
C3P C4P H4P 120.3 . . ?
C5P C4P C3P 119.50(18) . . ?
C5P C4P H4P 120.3 . . ?
C3T1 C4T1 H4TA 109.5 . . ?
C3T1 C4T1 H4TB 109.5 . . ?
C3T1 C4T1 H4TC 109.5 . . ?
H4TA C4T1 H4TB 109.5 . . ?
H4TA C4T1 H4TC 109.5 . . ?
H4TB C4T1 H4TC 109.5 . . ?
C3T2 C4T2 H4TD 109.5 . . ?
C3T2 C4T2 H4TE 109.5 . . ?
C3T2 C4T2 H4TF 109.5 . . ?
H4TD C4T2 H4TE 109.5 . . ?
H4TD C4T2 H4TF 109.5 . . ?
H4TE C4T2 H4TF 109.5 . . ?
N1 C5 C2P 126.60(15) . . ?
N4 C5 N1 108.29(15) . . ?
N4 C5 C2P 124.87(15) . . ?
C4B C5B H5B 119.4 . . ?
C6B C5B C4B 121.24(16) . . ?
C6B C5B H5B 119.4 . . ?
N1N C5N C4N 104.03(14) . . ?
N1N C5N C6N 110.83(14) . . ?
N1N C5N C9N 112.29(15) . . ?
C4N C5N C6N 113.23(14) . . ?
C4N C5N C9N 114.05(15) . . ?
C9N C5N C6N 102.68(14) . . ?
C4P C5P H5P 119.8 . . ?
C4P C5P C6P 120.38(17) . . ?
C6P C5P H5P 119.8 . . ?
C1B C6B H6B 119.5 . . ?
C5B C6B C1B 121.00(16) . . ?
C5B C6B H6B 119.5 . . ?
C5N C6N H6NA 110.9 . . ?
C5N C6N H6NB 110.9 . . ?
H6NA C6N H6NB 108.9 . . ?
C7N C6N C5N 104.30(14) . . ?
C7N C6N H6NA 110.9 . . ?
C7N C6N H6NB 110.9 . . ?
C1P C6P H6P 119.2 . . ?
C5P C6P C1P 121.68(17) . . ?
C5P C6P H6P 119.2 . . ?
C6N C7N H7NA 110.6 . . ?
C6N C7N H7NB 110.6 . . ?
H7NA C7N H7NB 108.7 . . ?
C8N C7N C6N 105.84(15) . . ?
C8N C7N H7NA 110.6 . . ?
C8N C7N H7NB 110.6 . . ?
C7N C8N H8NA 110.4 . . ?
C7N C8N H8NB 110.4 . . ?
C7N C8N C9N 106.65(15) . . ?
H8NA C8N H8NB 108.6 . . ?
C9N C8N H8NA 110.4 . . ?
C9N C8N H8NB 110.4 . . ?
C5N C9N H9NA 110.4 . . ?
C5N C9N H9NB 110.4 . . ?
C8N C9N C5N 106.84(15) . . ?
C8N C9N H9NA 110.4 . . ?
C8N C9N H9NB 110.4 . . ?
H9NA C9N H9NB 108.6 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1N C4N 1.213(2) . ?
N1 H1 0.92(3) . ?
N1 N2 1.345(2) . ?
N1 C5 1.335(2) . ?
N1N H1N 0.77(12) . ?
N1N C2N 1.283(2) . ?
N1N C5N 1.469(2) . ?
N2 N3 1.292(2) . ?
N3 N4 1.355(2) . ?
N3N C1M 1.468(2) . ?
N3N C2N 1.388(2) . ?
N3N C4N 1.376(2) . ?
N4 C5 1.321(2) . ?
C1 H1AA 0.9800 . ?
C1 H1AB 0.9800 . ?
C1 H1BC 0.9800 . ?
C1 H1BD 0.9800 . ?
C1 C2N 1.488(3) . ?
C1 C2T1 1.499(4) . ?
C1 C2T2 1.454(5) . ?
C1B C1P 1.486(2) . ?
C1B C2B 1.392(2) . ?
C1B C6B 1.392(2) . ?
C1M H1MA 0.9800 . ?
C1M H1MB 0.9800 . ?
C1M C4B 1.509(2) . ?
C1P C2P 1.406(2) . ?
C1P C6P 1.399(2) . ?
C2B H2B 0.9400 . ?
C2B C3B 1.379(2) . ?
C2P C3P 1.391(2) . ?
C2P C5 1.474(2) . ?
C2T1 H2TA 0.9800 . ?
C2T1 H2TB 0.9800 . ?
C2T1 C3T1 1.499(5) . ?
C2T2 H2TC 0.9800 . ?
C2T2 H2TD 0.9800 . ?
C2T2 C3T2 1.508(6) . ?
C3B H3B 0.9400 . ?
C3B C4B 1.388(2) . ?
C3P H3P 0.9400 . ?
C3P C4P 1.380(3) . ?
C3T1 H3TA 0.9800 . ?
C3T1 H3TB 0.9800 . ?
C3T1 C4T1 1.459(6) . ?
C3T2 H3TC 0.9800 . ?
C3T2 H3TD 0.9800 . ?
C3T2 C4T2 1.466(6) . ?
C4B C5B 1.388(2) . ?
C4N C5N 1.506(2) . ?
C4P H4P 0.9400 . ?
C4P C5P 1.365(3) . ?
C4T1 H4TA 0.9700 . ?
C4T1 H4TB 0.9700 . ?
C4T1 H4TC 0.9700 . ?
C4T2 H4TD 0.9700 . ?
C4T2 H4TE 0.9700 . ?
C4T2 H4TF 0.9700 . ?
C5B H5B 0.9400 . ?
C5B C6B 1.380(2) . ?
C5N C6N 1.533(2) . ?
C5N C9N 1.525(3) . ?
C5P H5P 0.9400 . ?
C5P C6P 1.379(3) . ?
C6B H6B 0.9400 . ?
C6N H6NA 0.9800 . ?
C6N H6NB 0.9800 . ?
C6N C7N 1.515(3) . ?
C6P H6P 0.9400 . ?
C7N H7NA 0.9800 . ?
C7N H7NB 0.9800 . ?
C7N C8N 1.512(3) . ?
C8N H8NA 0.9800 . ?
C8N H8NB 0.9800 . ?
C8N C9N 1.520(3) . ?
C9N H9NA 0.9800 . ?
C9N H9NB 0.9800 . ?
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
_geom_hbond_publ_flag
N1 H1 N1N 0.92(3) 1.86(3) 2.766(2) 172(2) 5 yes
N1N H1N N1 0.77(12) 2.03(12) 2.766(2) 160(10) 9_554 yes
C1M H1MA N3 0.98 2.58 3.527(2) 163.4 16 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1N C4N C5N N1N 178.33(18) . . . . ?
O1N C4N C5N C6N -61.3(2) . . . . ?
O1N C4N C5N C9N 55.7(2) . . . . ?
N1 N2 N3 N4 0.3(2) . . . . ?
N1N C5N C6N C7N -82.97(18) . . . . ?
N1N C5N C9N C8N 90.52(18) . . . . ?
N2 N1 C5 N4 -0.35(19) . . . . ?
N2 N1 C5 C2P -174.89(16) . . . . ?
N2 N3 N4 C5 -0.5(2) . . . . ?
N3 N4 C5 N1 0.5(2) . . . . ?
N3 N4 C5 C2P 175.15(16) . . . . ?
N3N C1M C4B C3B 87.07(19) . . . . ?
N3N C1M C4B C5B -95.96(18) . . . . ?
N3N C4N C5N N1N -2.16(17) . . . . ?
N3N C4N C5N C6N 118.24(16) . . . . ?
N3N C4N C5N C9N -124.82(16) . . . . ?
C1 C2T1 C3T1 C4T1 170.3(5) . . . . ?
C1 C2T2 C3T2 C4T2 -176.7(7) . . . . ?
C1B C1P C2P C3P 175.92(16) . . . . ?
C1B C1P C2P C5 -7.1(3) . . . . ?
C1B C1P C6P C5P -177.44(15) . . . . ?
C1B C2B C3B C4B 0.5(3) . . . . ?
C1M N3N C2N N1N -177.34(15) . . . . ?
C1M N3N C2N C1 5.4(3) . . . . ?
C1M N3N C4N O1N -1.4(3) . . . . ?
C1M N3N C4N C5N 179.03(14) . . . . ?
C1M C4B C5B C6B -176.75(15) . . . . ?
C1P C1B C2B C3B 179.50(15) . . . . ?
C1P C1B C6B C5B 179.47(15) . . . . ?
C1P C2P C3P C4P 1.9(3) . . . . ?
C1P C2P C5 N1 -52.1(3) . . . . ?
C1P C2P C5 N4 134.25(19) . . . . ?
C2B C1B C1P C2P 140.30(17) . . . . ?
C2B C1B C1P C6P -41.4(2) . . . . ?
C2B C1B C6B C5B -2.5(2) . . . . ?
C2B C3B C4B C1M 175.73(15) . . . . ?
C2B C3B C4B C5B -1.3(2) . . . . ?
C2N N1N C5N C4N 2.32(18) . . . . ?
C2N N1N C5N C6N -119.68(16) . . . . ?
C2N N1N C5N C9N 126.13(16) . . . . ?
C2N N3N C1M C4B 85.4(2) . . . . ?
C2N N3N C4N O1N -179.17(17) . . . . ?
C2N N3N C4N C5N 1.30(17) . . . . ?
C2N C1 C2T1 C3T1 169.8(4) . . . . ?
C2N C1 C2T2 C3T2 -179.1(5) . . . . ?
C2P C1P C6P C5P 0.9(2) . . . . ?
C2P C3P C4P C5P 0.1(3) . . . . ?
C2T1 C1 C2N N1N -84.4(3) . . . . ?
C2T1 C1 C2N N3N 92.6(3) . . . . ?
C2T2 C1 C2N N1N -36.7(4) . . . . ?
C2T2 C1 C2N N3N 140.2(4) . . . . ?
C3B C4B C5B C6B 0.3(2) . . . . ?
C3P C2P C5 N1 125.03(19) . . . . ?
C3P C2P C5 N4 -48.6(2) . . . . ?
C3P C4P C5P C6P -1.5(3) . . . . ?
C4B C5B C6B C1B 1.7(2) . . . . ?
C4N N3N C1M C4B -91.83(19) . . . . ?
C4N N3N C2N N1N 0.2(2) . . . . ?
C4N N3N C2N C1 -177.03(16) . . . . ?
C4N C5N C6N C7N 160.58(16) . . . . ?
C4N C5N C9N C8N -151.46(16) . . . . ?
C4P C5P C6P C1P 1.0(3) . . . . ?
C5 N1 N2 N3 0.06(19) . . . . ?
C5 C2P C3P C4P -175.32(18) . . . . ?
C5N N1N C2N N3N -1.7(2) . . . . ?
C5N N1N C2N C1 175.50(16) . . . . ?
C5N C6N C7N C8N -32.1(2) . . . . ?
C6B C1B C1P C2P -41.8(2) . . . . ?
C6B C1B C1P C6P 136.53(16) . . . . ?
C6B C1B C2B C3B 1.5(2) . . . . ?
C6N C5N C9N C8N -28.56(19) . . . . ?
C6N C7N C8N C9N 14.1(2) . . . . ?
C6P C1P C2P C3P -2.4(2) . . . . ?
C6P C1P C2P C5 174.63(15) . . . . ?
C7N C8N C9N C5N 9.3(2) . . . . ?
C9N C5N C6N C7N 37.13(19) . . . . ?
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
_smtbx_masks_void_content
1 0.000 0.000 -0.376 590.6 25.9 '2.4 water'
2 0.333 0.667 -0.683 590.6 25.9 '2.4 water'
3 0.667 0.333 -0.017 590.6 25.9 '2.4 water'
