#------------------------------------------------------------------------------
#$Date: 2023-09-05 23:20:52 +0300 (Tue, 05 Sep 2023) $
#$Revision: 286178 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/95/7159504.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_7159504
loop_
_publ_author_name
'Pamuła, Małgorzata'
'Bulatov, Evgeny'
'Martínez-Crespo, Luis'
'Kiesilä, Anniina'
'Naulapää, Julia'
'Kalenius, Elina'
'Helttunen, Kaisa'
_publ_section_title
;
 Anion binding and transport with meso-alkyl substituted two-armed
 calix[4]pyrroles bearing urea and hydroxyl groups.
;
_journal_issue                   32
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6595
_journal_page_last               6603
_journal_paper_doi               10.1039/d3ob00919j
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C32 H44 N4 O2'
_chemical_formula_sum            'C32 H44 N4 O2'
_chemical_formula_weight         516.71
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-02-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-03-15 deposited with the CCDC.	2023-07-24 downloaded from the CCDC.
;
_cell_angle_alpha                97.348(5)
_cell_angle_beta                 110.905(7)
_cell_angle_gamma                92.790(6)
_cell_formula_units_Z            2
_cell_length_a                   10.4551(8)
_cell_length_b                   10.5908(7)
_cell_length_c                   14.0367(9)
_cell_measurement_reflns_used    1955
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      71.2160
_cell_measurement_theta_min      3.3770
_cell_volume                     1432.54(19)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      120.01
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -87.00  -6.00   1.00   15.00    --  -41.90 125.00-180.00   81
  2  ω    -66.00  32.00   1.00   15.00    --  -41.90  37.00 120.00   98
  3  ω   -108.00 -18.00   1.00   15.00    --  -41.90 -37.00 -60.00   90
  4  ω    103.00 149.00   1.00   30.00    --  103.21  77.00-120.00   46
  5  ω     77.00 157.00   1.00   30.00    --  103.21  45.00 120.00   80
  6  ω     59.00 136.00   1.00   30.00    --  103.21 -77.00  30.00   77
  7  ω     72.00 178.00   1.00   30.00    --  103.21  15.00-150.00  106
  8  ω     75.00 112.00   1.00   30.00    --  103.21-125.00 -60.00   37
  9  ω    113.00 140.00   1.00   30.00    --  103.21 125.00 -30.00   27
 10  ω     39.00 106.00   1.00   30.00    --  103.21 -94.00-180.00   67
 11  ω     36.00 106.00   1.00   30.00    --  103.21 -94.00 -30.00   70
 12  ω     33.00 129.00   1.00   30.00    --  103.21 -45.00 -60.00   96
 13  ω     44.00 126.00   1.00   30.00    --  103.21 -45.00-180.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_unetI/netI     0.0687
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8838
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.521
_diffrn_reflns_theta_min         3.412
_exptl_absorpt_coefficient_mu    0.587
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.058
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.017
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         5395
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0523
_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)+(0.0510P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1265
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3763
_reflns_number_total             5395
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00919j2.cif
_cod_data_source_block           tiy014trans2
_cod_depositor_comments
'Adding full bibliography for 7159504--7159509.cif.'
_cod_original_cell_volume        1432.54(18)
_cod_database_code               7159504
_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   0.990
_shelx_estimated_absorpt_t_min   0.967
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C28(H28A,H28B), C29(H29A,H29B), C30(H30A,H30B), C31(H31A,
 H31B), C32(H32A,H32B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2B), C3(H3A), C7(H7), C8(H8), C12(H12), C13(H13), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.06936(17) 0.23634(15) -0.08331(11) 0.0250(4) Uani 1 1 d . . . . .
H1A H 0.015(3) 0.260(3) -0.083(2) 0.035(8) Uiso 1 1 d . . . . .
O2 O 0.74513(17) 1.15361(16) 0.58930(12) 0.0279(4) Uani 1 1 d . . . . .
H2A H 0.762(3) 1.069(4) 0.583(3) 0.056(10) Uiso 1 1 d . . . . .
N1 N -0.02410(19) 0.73401(17) 0.26511(14) 0.0194(4) Uani 1 1 d . . . . .
H1 H 0.053(3) 0.764(3) 0.318(2) 0.035(7) Uiso 1 1 d . . . . .
N2 N 0.23111(18) 0.58635(17) 0.24211(14) 0.0194(4) Uani 1 1 d . . . . .
H2 H 0.191(3) 0.633(2) 0.1909(19) 0.024(6) Uiso 1 1 d . . . . .
N3 N 0.39694(19) 0.85656(17) 0.24810(14) 0.0206(4) Uani 1 1 d . . . . .
H3 H 0.373(3) 0.850(3) 0.304(2) 0.033(7) Uiso 1 1 d . . . . .
N4 N 0.12329(18) 1.00228(17) 0.23498(14) 0.0197(4) Uani 1 1 d . . . . .
H4 H 0.111(3) 0.939(3) 0.181(2) 0.048(9) Uiso 1 1 d . . . . .
C1 C -0.1148(2) 0.8114(2) 0.20986(16) 0.0202(4) Uani 1 1 d . . . . .
C2 C -0.2111(2) 0.7343(2) 0.12658(16) 0.0232(5) Uani 1 1 d . . . . .
H2B H -0.286430 0.761704 0.074680 0.028 Uiso 1 1 calc R . . . .
C3 C -0.1780(2) 0.6063(2) 0.13178(16) 0.0224(5) Uani 1 1 d . . . . .
H3A H -0.227839 0.532799 0.084223 0.027 Uiso 1 1 calc R . . . .
C4 C -0.0612(2) 0.6074(2) 0.21776(16) 0.0201(4) Uani 1 1 d . . . . .
C5 C 0.0143(2) 0.4997(2) 0.26482(16) 0.0199(4) Uani 1 1 d . . . . .
C6 C 0.1688(2) 0.52584(19) 0.29761(16) 0.0186(4) Uani 1 1 d . . . . .
C7 C 0.2708(2) 0.4861(2) 0.37687(16) 0.0220(5) Uani 1 1 d . . . . .
H7 H 0.258376 0.441386 0.427922 0.026 Uiso 1 1 calc R . . . .
C8 C 0.3984(2) 0.5234(2) 0.36940(17) 0.0232(5) Uani 1 1 d . . . . .
H8 H 0.486698 0.507908 0.414379 0.028 Uiso 1 1 calc R . . . .
C9 C 0.3718(2) 0.58615(19) 0.28541(16) 0.0197(4) Uani 1 1 d . . . . .
C10 C 0.4681(2) 0.6315(2) 0.23591(16) 0.0215(5) Uani 1 1 d . . . . .
C11 C 0.4318(2) 0.7550(2) 0.19346(16) 0.0198(4) Uani 1 1 d . . . . .
C12 C 0.4414(2) 0.7962(2) 0.10739(17) 0.0235(5) Uani 1 1 d . . . . .
H12 H 0.463599 0.746548 0.055157 0.028 Uiso 1 1 calc R . . . .
C13 C 0.4126(2) 0.9251(2) 0.10980(17) 0.0237(5) Uani 1 1 d . . . . .
H13 H 0.412682 0.977575 0.059775 0.028 Uiso 1 1 calc R . . . .
C14 C 0.3844(2) 0.9613(2) 0.19704(16) 0.0202(4) Uani 1 1 d . . . . .
C15 C 0.3552(2) 1.0903(2) 0.24021(17) 0.0217(5) Uani 1 1 d . . . . .
C16 C 0.2449(2) 1.07984(19) 0.28580(16) 0.0204(4) Uani 1 1 d . . . . .
C17 C 0.2343(2) 1.1473(2) 0.37271(17) 0.0249(5) Uani 1 1 d . . . . .
H17 H 0.302261 1.208708 0.422696 0.030 Uiso 1 1 calc R . . . .
C18 C 0.1035(2) 1.1083(2) 0.37394(17) 0.0249(5) Uani 1 1 d . . . . .
H18 H 0.068444 1.139081 0.425388 0.030 Uiso 1 1 calc R . . . .
C19 C 0.0359(2) 1.0186(2) 0.28825(17) 0.0219(5) Uani 1 1 d . . . . .
C20 C -0.1087(2) 0.9527(2) 0.24793(18) 0.0241(5) Uani 1 1 d . . . . .
C21 C -0.0211(2) 0.4815(2) 0.36031(17) 0.0261(5) Uani 1 1 d . . . . .
H21A H 0.021109 0.407394 0.389008 0.039 Uiso 1 1 calc GR . . . .
H21B H -0.121215 0.467202 0.340038 0.039 Uiso 1 1 calc GR . . . .
H21C H 0.014331 0.558303 0.412510 0.039 Uiso 1 1 calc GR . . . .
C22 C 0.6169(2) 0.6531(2) 0.31617(18) 0.0272(5) Uani 1 1 d . . . . .
H22A H 0.680117 0.678435 0.283016 0.041 Uiso 1 1 calc GR . . . .
H22B H 0.642108 0.573632 0.343861 0.041 Uiso 1 1 calc GR . . . .
H22C H 0.622679 0.720795 0.372529 0.041 Uiso 1 1 calc GR . . . .
C23 C 0.4630(3) 0.5261(2) 0.14747(19) 0.0289(5) Uani 1 1 d . . . . .
H23A H 0.369391 0.511315 0.095474 0.043 Uiso 1 1 calc GR . . . .
H23B H 0.489024 0.446804 0.175088 0.043 Uiso 1 1 calc GR . . . .
H23C H 0.527141 0.553317 0.115669 0.043 Uiso 1 1 calc GR . . . .
C24 C 0.3048(2) 1.1712(2) 0.15196(18) 0.0281(5) Uani 1 1 d . . . . .
H24A H 0.220417 1.127384 0.098090 0.042 Uiso 1 1 calc GR . . . .
H24B H 0.376059 1.182237 0.122606 0.042 Uiso 1 1 calc GR . . . .
H24C H 0.286185 1.255243 0.179301 0.042 Uiso 1 1 calc GR . . . .
C25 C -0.1682(3) 0.9676(2) 0.3335(2) 0.0388(6) Uani 1 1 d . . . . .
H25A H -0.261578 0.923610 0.307284 0.058 Uiso 1 1 calc GR . . . .
H25B H -0.171168 1.058630 0.355589 0.058 Uiso 1 1 calc GR . . . .
H25C H -0.109966 0.929983 0.392345 0.058 Uiso 1 1 calc GR . . . .
C26 C -0.1994(2) 1.0163(2) 0.1574(2) 0.0338(6) Uani 1 1 d . . . . .
H26A H -0.166142 1.002454 0.100258 0.051 Uiso 1 1 calc GR . . . .
H26B H -0.194638 1.108307 0.180430 0.051 Uiso 1 1 calc GR . . . .
H26C H -0.294946 0.978333 0.134194 0.051 Uiso 1 1 calc GR . . . .
C27 C -0.0360(2) 0.3724(2) 0.18813(16) 0.0218(5) Uani 1 1 d . . . . .
H27A H 0.008746 0.302694 0.224137 0.026 Uiso 1 1 calc R . . . .
H27B H -0.136279 0.354807 0.170577 0.026 Uiso 1 1 calc R . . . .
C28 C -0.0096(2) 0.3663(2) 0.08725(16) 0.0215(5) Uani 1 1 d . . . . .
H28A H -0.051135 0.436869 0.050755 0.026 Uiso 1 1 calc R . . . .
H28B H 0.090738 0.377118 0.102699 0.026 Uiso 1 1 calc R . . . .
C29 C -0.0709(2) 0.2393(2) 0.01879(16) 0.0222(5) Uani 1 1 d . . . . .
H29A H -0.018539 0.170429 0.050759 0.027 Uiso 1 1 calc R . . . .
H29B H -0.167122 0.221992 0.014037 0.027 Uiso 1 1 calc R . . . .
C30 C 0.4892(2) 1.1655(2) 0.32108(17) 0.0236(5) Uani 1 1 d . . . . .
H30A H 0.555487 1.177151 0.286416 0.028 Uiso 1 1 calc R . . . .
H30B H 0.467134 1.251655 0.343030 0.028 Uiso 1 1 calc R . . . .
C31 C 0.5609(2) 1.1067(2) 0.41789(17) 0.0235(5) Uani 1 1 d . . . . .
H31A H 0.495247 1.090069 0.452193 0.028 Uiso 1 1 calc R . . . .
H31B H 0.592343 1.023968 0.398449 0.028 Uiso 1 1 calc R . . . .
C32 C 0.6829(2) 1.1961(2) 0.49160(17) 0.0248(5) Uani 1 1 d . . . . .
H32A H 0.752699 1.204296 0.459556 0.030 Uiso 1 1 calc R . . . .
H32B H 0.652600 1.281968 0.503150 0.030 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 0.0181 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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 -5 0.0200
1 0 5 0.0200
1 5 -5 0.0220
-1 -5 5 0.0220
2 5 2 0.0262
-2 -5 -2 0.0262
-5 1 4 0.0084
5 -1 -4 0.0084
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
C29 O1 H1A 112.5(18) . . ?
C32 O2 H2A 113(2) . . ?
C1 N1 H1 123.1(18) . . ?
C1 N1 C4 110.21(18) . . ?
C4 N1 H1 126.1(18) . . ?
C6 N2 H2 127.2(16) . . ?
C6 N2 C9 110.26(18) . . ?
C9 N2 H2 121.8(16) . . ?
C11 N3 H3 123.6(18) . . ?
C11 N3 C14 109.91(18) . . ?
C14 N3 H3 125.8(18) . . ?
C16 N4 H4 123(2) . . ?
C19 N4 H4 125(2) . . ?
C19 N4 C16 110.40(19) . . ?
N1 C1 C20 122.27(19) . . ?
C2 C1 N1 107.33(19) . . ?
C2 C1 C20 130.1(2) . . ?
C1 C2 H2B 126.1 . . ?
C1 C2 C3 107.83(19) . . ?
C3 C2 H2B 126.1 . . ?
C2 C3 H3A 126.0 . . ?
C4 C3 C2 108.02(19) . . ?
C4 C3 H3A 126.0 . . ?
N1 C4 C5 122.05(18) . . ?
C3 C4 N1 106.60(19) . . ?
C3 C4 C5 131.2(2) . . ?
C4 C5 C6 112.57(17) . . ?
C4 C5 C21 108.10(18) . . ?
C4 C5 C27 110.48(17) . . ?
C6 C5 C21 109.03(17) . . ?
C6 C5 C27 109.41(17) . . ?
C21 C5 C27 107.09(17) . . ?
N2 C6 C5 123.35(18) . . ?
C7 C6 N2 107.19(19) . . ?
C7 C6 C5 129.2(2) . . ?
C6 C7 H7 126.0 . . ?
C6 C7 C8 107.93(19) . . ?
C8 C7 H7 126.0 . . ?
C7 C8 H8 126.1 . . ?
C9 C8 C7 107.81(19) . . ?
C9 C8 H8 126.1 . . ?
N2 C9 C10 123.14(19) . . ?
C8 C9 N2 106.80(19) . . ?
C8 C9 C10 129.5(2) . . ?
C9 C10 C11 112.59(17) . . ?
C9 C10 C22 109.52(18) . . ?
C9 C10 C23 108.52(18) . . ?
C11 C10 C22 108.58(18) . . ?
C11 C10 C23 109.33(18) . . ?
C23 C10 C22 108.21(18) . . ?
N3 C11 C10 122.12(19) . . ?
C12 C11 N3 107.01(19) . . ?
C12 C11 C10 130.4(2) . . ?
C11 C12 H12 125.9 . . ?
C11 C12 C13 108.1(2) . . ?
C13 C12 H12 125.9 . . ?
C12 C13 H13 126.0 . . ?
C14 C13 C12 108.0(2) . . ?
C14 C13 H13 126.0 . . ?
N3 C14 C15 122.89(19) . . ?
C13 C14 N3 106.94(19) . . ?
C13 C14 C15 130.0(2) . . ?
C14 C15 C24 108.88(18) . . ?
C14 C15 C30 110.64(18) . . ?
C16 C15 C14 112.63(18) . . ?
C16 C15 C24 107.72(18) . . ?
C16 C15 C30 110.63(18) . . ?
C24 C15 C30 106.06(18) . . ?
N4 C16 C15 121.92(19) . . ?
C17 C16 N4 107.1(2) . . ?
C17 C16 C15 130.7(2) . . ?
C16 C17 H17 126.3 . . ?
C16 C17 C18 107.38(19) . . ?
C18 C17 H17 126.3 . . ?
C17 C18 H18 125.8 . . ?
C19 C18 C17 108.5(2) . . ?
C19 C18 H18 125.8 . . ?
N4 C19 C20 122.54(19) . . ?
C18 C19 N4 106.6(2) . . ?
C18 C19 C20 130.7(2) . . ?
C1 C20 C25 108.45(19) . . ?
C1 C20 C26 108.51(19) . . ?
C19 C20 C1 112.46(18) . . ?
C19 C20 C25 109.8(2) . . ?
C19 C20 C26 108.97(18) . . ?
C25 C20 C26 108.6(2) . . ?
C5 C21 H21A 109.5 . . ?
C5 C21 H21B 109.5 . . ?
C5 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C10 C22 H22A 109.5 . . ?
C10 C22 H22B 109.5 . . ?
C10 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C10 C23 H23A 109.5 . . ?
C10 C23 H23B 109.5 . . ?
C10 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C15 C24 H24A 109.5 . . ?
C15 C24 H24B 109.5 . . ?
C15 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C20 C25 H25A 109.5 . . ?
C20 C25 H25B 109.5 . . ?
C20 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C20 C26 H26A 109.5 . . ?
C20 C26 H26B 109.5 . . ?
C20 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C5 C27 H27A 108.1 . . ?
C5 C27 H27B 108.1 . . ?
H27A C27 H27B 107.3 . . ?
C28 C27 C5 116.80(18) . . ?
C28 C27 H27A 108.1 . . ?
C28 C27 H27B 108.1 . . ?
C27 C28 H28A 109.6 . . ?
C27 C28 H28B 109.6 . . ?
H28A C28 H28B 108.1 . . ?
C29 C28 C27 110.36(18) . . ?
C29 C28 H28A 109.6 . . ?
C29 C28 H28B 109.6 . . ?
O1 C29 C28 112.61(18) . . ?
O1 C29 H29A 109.1 . . ?
O1 C29 H29B 109.1 . . ?
C28 C29 H29A 109.1 . . ?
C28 C29 H29B 109.1 . . ?
H29A C29 H29B 107.8 . . ?
C15 C30 H30A 108.0 . . ?
C15 C30 H30B 108.0 . . ?
H30A C30 H30B 107.3 . . ?
C31 C30 C15 117.08(18) . . ?
C31 C30 H30A 108.0 . . ?
C31 C30 H30B 108.0 . . ?
C30 C31 H31A 109.6 . . ?
C30 C31 H31B 109.6 . . ?
H31A C31 H31B 108.1 . . ?
C32 C31 C30 110.24(18) . . ?
C32 C31 H31A 109.6 . . ?
C32 C31 H31B 109.6 . . ?
O2 C32 C31 113.05(19) . . ?
O2 C32 H32A 109.0 . . ?
O2 C32 H32B 109.0 . . ?
C31 C32 H32A 109.0 . . ?
C31 C32 H32B 109.0 . . ?
H32A C32 H32B 107.8 . . ?
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
O1 H1A 0.90(3) . ?
O1 C29 1.436(3) . ?
O2 H2A 0.92(4) . ?
O2 C32 1.434(3) . ?
N1 H1 0.89(3) . ?
N1 C1 1.373(3) . ?
N1 C4 1.389(3) . ?
N2 H2 0.91(3) . ?
N2 C6 1.375(3) . ?
N2 C9 1.377(3) . ?
N3 H3 0.91(3) . ?
N3 C11 1.380(3) . ?
N3 C14 1.382(3) . ?
N4 H4 0.92(3) . ?
N4 C16 1.379(3) . ?
N4 C19 1.376(3) . ?
C1 C2 1.372(3) . ?
C1 C20 1.513(3) . ?
C2 H2B 0.9500 . ?
C2 C3 1.420(3) . ?
C3 H3A 0.9500 . ?
C3 C4 1.375(3) . ?
C4 C5 1.506(3) . ?
C5 C6 1.513(3) . ?
C5 C21 1.544(3) . ?
C5 C27 1.552(3) . ?
C6 C7 1.367(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.416(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.376(3) . ?
C9 C10 1.505(3) . ?
C10 C11 1.516(3) . ?
C10 C22 1.545(3) . ?
C10 C23 1.543(3) . ?
C11 C12 1.370(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.411(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.372(3) . ?
C14 C15 1.513(3) . ?
C15 C16 1.511(3) . ?
C15 C24 1.548(3) . ?
C15 C30 1.553(3) . ?
C16 C17 1.375(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.416(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.373(3) . ?
C19 C20 1.510(3) . ?
C20 C25 1.533(3) . ?
C20 C26 1.545(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.530(3) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C29 1.514(3) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C30 C31 1.527(3) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.512(3) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
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 O2 0.89(3) 2.11(3) 2.981(3) 165(3) 2_676 yes
N2 H2 O1 0.91(3) 2.27(3) 3.169(2) 169(2) 2_565 yes
N3 H3 O2 0.91(3) 2.26(3) 3.145(3) 164(2) 2_676 yes
N4 H4 O1 0.92(3) 2.08(3) 2.977(2) 164(3) 2_565 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
N1 C1 C2 C3 0.2(2) . . . . ?
N1 C1 C20 C19 45.7(3) . . . . ?
N1 C1 C20 C25 -75.9(3) . . . . ?
N1 C1 C20 C26 166.3(2) . . . . ?
N1 C4 C5 C6 -49.4(3) . . . . ?
N1 C4 C5 C21 71.1(3) . . . . ?
N1 C4 C5 C27 -172.00(18) . . . . ?
N2 C6 C7 C8 0.0(2) . . . . ?
N2 C9 C10 C11 43.9(3) . . . . ?
N2 C9 C10 C22 164.78(19) . . . . ?
N2 C9 C10 C23 -77.3(2) . . . . ?
N3 C11 C12 C13 0.3(2) . . . . ?
N3 C14 C15 C16 -43.7(3) . . . . ?
N3 C14 C15 C24 -163.09(19) . . . . ?
N3 C14 C15 C30 80.7(2) . . . . ?
N4 C16 C17 C18 0.3(2) . . . . ?
N4 C19 C20 C1 47.5(3) . . . . ?
N4 C19 C20 C25 168.3(2) . . . . ?
N4 C19 C20 C26 -72.9(3) . . . . ?
C1 N1 C4 C3 -0.5(2) . . . . ?
C1 N1 C4 C5 -175.94(19) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C2 C1 C20 C19 -141.9(2) . . . . ?
C2 C1 C20 C25 96.6(3) . . . . ?
C2 C1 C20 C26 -21.3(3) . . . . ?
C2 C3 C4 N1 0.6(2) . . . . ?
C2 C3 C4 C5 175.5(2) . . . . ?
C3 C4 C5 C6 136.4(2) . . . . ?
C3 C4 C5 C21 -103.1(3) . . . . ?
C3 C4 C5 C27 13.8(3) . . . . ?
C4 N1 C1 C2 0.2(2) . . . . ?
C4 N1 C1 C20 174.09(19) . . . . ?
C4 C5 C6 N2 -38.0(3) . . . . ?
C4 C5 C6 C7 149.2(2) . . . . ?
C4 C5 C27 C28 63.6(2) . . . . ?
C5 C6 C7 C8 173.7(2) . . . . ?
C5 C27 C28 C29 -177.04(18) . . . . ?
C6 N2 C9 C8 0.4(2) . . . . ?
C6 N2 C9 C10 172.76(18) . . . . ?
C6 C5 C27 C28 -60.9(2) . . . . ?
C6 C7 C8 C9 0.2(2) . . . . ?
C7 C8 C9 N2 -0.4(2) . . . . ?
C7 C8 C9 C10 -172.1(2) . . . . ?
C8 C9 C10 C11 -145.7(2) . . . . ?
C8 C9 C10 C22 -24.8(3) . . . . ?
C8 C9 C10 C23 93.2(3) . . . . ?
C9 N2 C6 C5 -174.46(18) . . . . ?
C9 N2 C6 C7 -0.3(2) . . . . ?
C9 C10 C11 N3 44.0(3) . . . . ?
C9 C10 C11 C12 -144.8(2) . . . . ?
C10 C11 C12 C13 -172.0(2) . . . . ?
C11 N3 C14 C13 -0.4(2) . . . . ?
C11 N3 C14 C15 -176.33(19) . . . . ?
C11 C12 C13 C14 -0.5(3) . . . . ?
C12 C13 C14 N3 0.5(2) . . . . ?
C12 C13 C14 C15 176.1(2) . . . . ?
C13 C14 C15 C16 141.4(2) . . . . ?
C13 C14 C15 C24 22.0(3) . . . . ?
C13 C14 C15 C30 -94.2(3) . . . . ?
C14 N3 C11 C10 173.09(19) . . . . ?
C14 N3 C11 C12 0.1(2) . . . . ?
C14 C15 C16 N4 -46.1(3) . . . . ?
C14 C15 C16 C17 141.1(2) . . . . ?
C14 C15 C30 C31 -62.5(3) . . . . ?
C15 C16 C17 C18 173.9(2) . . . . ?
C15 C30 C31 C32 -175.84(19) . . . . ?
C16 N4 C19 C18 0.2(2) . . . . ?
C16 N4 C19 C20 175.96(19) . . . . ?
C16 C15 C30 C31 63.1(2) . . . . ?
C16 C17 C18 C19 -0.2(2) . . . . ?
C17 C18 C19 N4 0.0(2) . . . . ?
C17 C18 C19 C20 -175.3(2) . . . . ?
C18 C19 C20 C1 -137.9(2) . . . . ?
C18 C19 C20 C25 -17.1(3) . . . . ?
C18 C19 C20 C26 101.8(3) . . . . ?
C19 N4 C16 C15 -174.62(18) . . . . ?
C19 N4 C16 C17 -0.3(2) . . . . ?
C20 C1 C2 C3 -173.1(2) . . . . ?
C21 C5 C6 N2 -157.95(19) . . . . ?
C21 C5 C6 C7 29.2(3) . . . . ?
C21 C5 C27 C28 -178.92(18) . . . . ?
C22 C10 C11 N3 -77.5(2) . . . . ?
C22 C10 C11 C12 93.7(3) . . . . ?
C23 C10 C11 N3 164.66(19) . . . . ?
C23 C10 C11 C12 -24.1(3) . . . . ?
C24 C15 C16 N4 74.0(2) . . . . ?
C24 C15 C16 C17 -98.8(3) . . . . ?
C24 C15 C30 C31 179.62(19) . . . . ?
C27 C5 C6 N2 85.2(2) . . . . ?
C27 C5 C6 C7 -87.6(3) . . . . ?
C27 C28 C29 O1 170.33(17) . . . . ?
C30 C15 C16 N4 -170.51(18) . . . . ?
C30 C15 C16 C17 16.7(3) . . . . ?
C30 C31 C32 O2 173.03(18) . . . . ?
