#------------------------------------------------------------------------------
#$Date: 2023-09-05 23:20:52 +0300 (Tue, 05 Sep 2023) $
#$Revision: 286178 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/95/7159506.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_7159506
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
'2(Cl), 2(C32 H44 N4 O2), 0.5(C4 H12 O2), 2(C4 H12 N)'
_chemical_formula_sum            'C74 H118 Cl2 N10 O5'
_chemical_formula_weight         1298.68
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2023-02-01
_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                90
_cell_angle_beta                 108.690(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.0787(9)
_cell_length_b                   18.1527(5)
_cell_length_c                   22.8772(12)
_cell_measurement_reflns_used    8894
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      76.4350
_cell_measurement_theta_min      3.1580
_cell_volume                     7111.9(6)
_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 5.1947
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00 -24.00   1.00    6.00    --  -41.92 -37.00-150.00   86
  2  ω   -114.00 -19.00   1.00    6.00    --  -41.92 -37.00 120.00   95
  3  ω    -86.00 -54.00   1.00    6.00    --  -41.92 125.00  30.00   32
  4  ω     55.00  82.00   1.00    6.00    --   41.92-122.00 137.00   27
  5  ω     36.00 109.00   1.00   30.00    --  112.00-111.00-180.00   73
  6  ω     59.00 109.00   1.00   30.00    --  112.00-111.00-150.00   50
  7  ω     87.00 139.00   1.00   30.00    --  112.00 178.00 -30.00   52
  8  ω     60.00 177.00   1.00   30.00    --  112.00  15.00 -30.00  117
  9  ω    103.00 177.00   1.00   30.00    --  112.00  30.00  30.00   74
 10  ω     83.00 109.00   1.00   30.00    --  112.00-111.00 120.00   26
 11  ω     52.00  91.00   1.00   30.00    --  112.00 -45.00 -60.00   39
 12  ω    111.00 138.00   1.00   30.00    --  112.00 -45.00 -60.00   27
 13  ω     83.00 134.00   1.00   30.00    --  112.00 178.00-150.00   51
 14  ω     36.00  76.00   1.00   30.00    --  112.00-111.00-120.00   40
 15  ω     41.00  94.00   1.00   30.00    --  112.00 -61.00-120.00   53
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            18056
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.581
_diffrn_reflns_theta_min         3.176
_exptl_absorpt_coefficient_mu    1.263
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.213
_exptl_crystal_description       block
_exptl_crystal_F_000             2824
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.091
_refine_diff_density_max         0.901
_refine_diff_density_min         -0.757
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       0.00015(3)
_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   1.144
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     454
_refine_ls_number_reflns         7343
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.144
_refine_ls_R_factor_all          0.1019
_refine_ls_R_factor_gt           0.0954
_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)+(0.0617P)²+42.9873P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2272
_refine_ls_wR_factor_ref         0.2306
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6502
_reflns_number_total             7343
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00919j2.cif
_cod_data_source_block           tiy-015-cis-6_a
_cod_depositor_comments
'Adding full bibliography for 7159504--7159509.cif.'
_cod_database_code               7159506
_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   0.894
_shelx_estimated_absorpt_t_min   0.863
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C26A) = Uanis(C26)
3. Others
 Fixed Sof: H1B(0.5) H1A(0.5) H2B(0.5) H2A(0.5) H25A(0.5) H25B(0.5) H25C(0.5)
 H25D(0.5) C26(0.5) H26A(0.5) H26B(0.5) C26A(0.5) H26C(0.5) H26D(0.5) H1S(0.5)
 C1S(0.5) H1SA(0.5) H1SB(0.5) C2S(0.5) H2SA(0.5) H2SB(0.5) H2SC(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C25(H25A,H25B), C25(H25C,H25D), C30(H30A,H30B), C31(H31A,
 H31B), C32(H32A,H32B), C26(H26A,H26B), C26A(H26C,H26D), C1S(H1SA,H1SB)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2C), C3(H3A), C7(H7), C8(H8), C12(H12), C13(H13), C17(H17), C18(H18)
4.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C27(H27A,H27B,
 H27C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C2S(H2SA,H2SB,H2SC), C1A(H1AA,
 H1AB,H1AC), C2A(H2AA,H2AB,H2AC), C3A(H3AA,H3AB,H3AC), C4A(H4AA,H4AB,H4AC)
4.d Idealised tetrahedral OH refined with everything fixed:
 O1(H1A)
4.e Idealised tetrahedral OH refined as rotating group:
 O1(H1B), O2(H2B), O2(H2A), O1S(H1S)
;
_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+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
Cl1 Cl 0.35924(5) 0.35806(5) 0.75374(4) 0.0322(2) Uani 1 1 d . . . . .
O1 O 0.3873(2) 0.2804(3) 0.89480(18) 0.0659(11) Uani 1 1 d . . . . .
H1B H 0.395579 0.301121 0.864632 0.099 Uiso 0.5 1 calc GR . . A 2
H1A H 0.374528 0.239712 0.906147 0.099 Uiso 0.5 1 calc . . . B 1
O2 O 0.2045(2) 0.33763(19) 0.59070(15) 0.0502(8) Uani 1 1 d . . . . .
H2B H 0.176069 0.310267 0.604090 0.075 Uiso 0.5 1 calc GR . . C 4
H2A H 0.217308 0.312473 0.564658 0.075 Uiso 0.5 1 calc GR . . D 3
N1 N 0.49597(19) 0.44833(17) 0.86276(14) 0.0283(7) Uani 1 1 d . . . . .
H1 H 0.465(3) 0.428(3) 0.836(2) 0.035(12) Uiso 1 1 d . . . . .
N2 N 0.54309(18) 0.35739(17) 0.75238(14) 0.0278(6) Uani 1 1 d . . . . .
H2 H 0.493(3) 0.359(2) 0.751(2) 0.033(12) Uiso 1 1 d . . . . .
N3 N 0.40809(18) 0.45353(17) 0.64462(14) 0.0279(6) Uani 1 1 d . . . . .
H3 H 0.395(3) 0.424(3) 0.670(2) 0.046(14) Uiso 1 1 d . . . . .
N4 N 0.35796(18) 0.54077(17) 0.75626(14) 0.0270(6) Uani 1 1 d . . . . .
H4 H 0.357(3) 0.490(3) 0.753(2) 0.035(12) Uiso 1 1 d . . . . .
C1 C 0.4841(2) 0.5140(2) 0.88885(17) 0.0303(8) Uani 1 1 d . . . . .
C2 C 0.5551(3) 0.5339(3) 0.9293(2) 0.0483(12) Uani 1 1 d . . . . .
H2C H 0.565836 0.577261 0.953787 0.058 Uiso 1 1 calc R . . . .
C3 C 0.6099(3) 0.4783(3) 0.9281(2) 0.0517(13) Uani 1 1 d . . . . .
H3A H 0.663700 0.478053 0.951952 0.062 Uiso 1 1 calc R . . . .
C4 C 0.5721(2) 0.4251(2) 0.88667(17) 0.0319(8) Uani 1 1 d . . . . .
C5 C 0.6007(2) 0.3527(2) 0.86970(17) 0.0307(8) Uani 1 1 d . . . . .
C6 C 0.6076(2) 0.35537(19) 0.80530(17) 0.0290(8) Uani 1 1 d . . . . .
C7 C 0.6718(2) 0.3558(2) 0.78607(19) 0.0343(9) Uani 1 1 d . . . . .
H7 H 0.724634 0.354835 0.812152 0.041 Uiso 1 1 calc R . . . .
C8 C 0.6464(2) 0.3578(2) 0.72068(19) 0.0331(8) Uani 1 1 d . . . . .
H8 H 0.679034 0.358538 0.695366 0.040 Uiso 1 1 calc R . . . .
C9 C 0.5663(2) 0.35843(19) 0.70044(17) 0.0279(7) Uani 1 1 d . . . . .
C10 C 0.5087(2) 0.3607(2) 0.63574(17) 0.0286(7) Uani 1 1 d . . . . .
C11 C 0.4679(2) 0.4348(2) 0.62232(16) 0.0270(7) Uani 1 1 d . . . . .
C12 C 0.4781(2) 0.4936(2) 0.58754(18) 0.0314(8) Uani 1 1 d . . . . .
H12 H 0.515630 0.496711 0.566533 0.038 Uiso 1 1 calc R . . . .
C13 C 0.4229(2) 0.5484(2) 0.58862(18) 0.0321(8) Uani 1 1 d . . . . .
H13 H 0.416739 0.594864 0.568473 0.038 Uiso 1 1 calc R . . . .
C14 C 0.3794(2) 0.5224(2) 0.62416(16) 0.0278(7) Uani 1 1 d . . . . .
C15 C 0.3116(2) 0.5563(2) 0.63951(17) 0.0295(8) Uani 1 1 d . . . . .
C16 C 0.3375(2) 0.5860(2) 0.70512(17) 0.0282(7) Uani 1 1 d . . . . .
C17 C 0.3471(2) 0.6576(2) 0.72588(19) 0.0324(8) Uani 1 1 d . . . . .
H17 H 0.337651 0.700584 0.700931 0.039 Uiso 1 1 calc R . . . .
C18 C 0.3736(2) 0.6555(2) 0.79134(19) 0.0341(8) Uani 1 1 d . . . . .
H18 H 0.384865 0.697060 0.817965 0.041 Uiso 1 1 calc R . . . .
C19 C 0.3800(2) 0.5835(2) 0.80947(17) 0.0285(8) Uani 1 1 d . . . . .
C20 C 0.4049(2) 0.5503(2) 0.87338(17) 0.0299(8) Uani 1 1 d . . . . .
C21 C 0.4101(2) 0.6116(2) 0.92043(18) 0.0378(9) Uani 1 1 d . . . . .
H21A H 0.450366 0.647083 0.919034 0.057 Uiso 1 1 calc GR . . . .
H21B H 0.423567 0.590340 0.961885 0.057 Uiso 1 1 calc GR . . . .
H21C H 0.359578 0.636806 0.910473 0.057 Uiso 1 1 calc GR . . . .
C22 C 0.3442(2) 0.4931(2) 0.87922(18) 0.0354(9) Uani 1 1 d . . . . .
H22A H 0.292722 0.516496 0.868780 0.053 Uiso 1 1 calc GR . . . .
H22B H 0.359439 0.474642 0.921678 0.053 Uiso 1 1 calc GR . . . .
H22C H 0.341955 0.452052 0.850911 0.053 Uiso 1 1 calc GR . . . .
C23 C 0.6825(2) 0.3375(2) 0.9156(2) 0.0384(10) Uani 1 1 d . . . . .
H23A H 0.702789 0.291350 0.904508 0.058 Uiso 1 1 calc GR . . . .
H23B H 0.679185 0.333379 0.957430 0.058 Uiso 1 1 calc GR . . . .
H23C H 0.717661 0.378065 0.914196 0.058 Uiso 1 1 calc GR . . . .
C24 C 0.5447(2) 0.2885(2) 0.87260(17) 0.0325(8) Uani 1 1 d . . . . .
H24A H 0.493862 0.297130 0.840296 0.039 Uiso 1 1 calc R . . . .
H24B H 0.566391 0.242221 0.861891 0.039 Uiso 1 1 calc R . . . .
C25 C 0.5294(3) 0.2766(4) 0.9338(2) 0.0581(14) Uani 1 1 d . . . . .
H25A H 0.530551 0.222878 0.941723 0.070 Uiso 0.5 1 calc R . . E 1
H25B H 0.573253 0.298757 0.966909 0.070 Uiso 0.5 1 calc R . . E 1
H25C H 0.572803 0.245621 0.959432 0.070 Uiso 0.5 1 calc R . . F 2
H25D H 0.535285 0.325308 0.954172 0.070 Uiso 0.5 1 calc R . . F 2
C27 C 0.5537(3) 0.3490(2) 0.58958(19) 0.0365(9) Uani 1 1 d . . . . .
H27A H 0.517162 0.350802 0.547397 0.055 Uiso 1 1 calc GR . . . .
H27B H 0.579587 0.300852 0.596953 0.055 Uiso 1 1 calc GR . . . .
H27C H 0.592980 0.387844 0.595029 0.055 Uiso 1 1 calc GR . . . .
C28 C 0.4476(2) 0.2990(2) 0.62673(18) 0.0315(8) Uani 1 1 d . . . . .
H28A H 0.418986 0.305522 0.656239 0.047 Uiso 1 1 calc GR . . . .
H28B H 0.473908 0.251029 0.633630 0.047 Uiso 1 1 calc GR . . . .
H28C H 0.410911 0.301044 0.584593 0.047 Uiso 1 1 calc GR . . . .
C29 C 0.2792(3) 0.6208(2) 0.59525(19) 0.0382(9) Uani 1 1 d . . . . .
H29A H 0.320248 0.657710 0.600046 0.057 Uiso 1 1 calc GR . . . .
H29B H 0.235079 0.643071 0.604816 0.057 Uiso 1 1 calc GR . . . .
H29C H 0.261653 0.602637 0.552652 0.057 Uiso 1 1 calc GR . . . .
C30 C 0.2461(2) 0.4975(2) 0.63168(17) 0.0305(8) Uani 1 1 d . . . . .
H30A H 0.267453 0.456280 0.660542 0.037 Uiso 1 1 calc R . . . .
H30B H 0.203004 0.519936 0.643414 0.037 Uiso 1 1 calc R . . . .
C31 C 0.2130(3) 0.4665(3) 0.56644(19) 0.0434(10) Uani 1 1 d . . . . .
H31A H 0.182901 0.505702 0.538918 0.052 Uiso 1 1 calc R . . . .
H31B H 0.256972 0.452710 0.551684 0.052 Uiso 1 1 calc R . . . .
C32 C 0.1608(3) 0.4001(3) 0.5611(2) 0.0470(11) Uani 1 1 d . . . . .
H32A H 0.120137 0.411390 0.580259 0.056 Uiso 1 1 calc R . . . .
H32B H 0.134358 0.388787 0.517007 0.056 Uiso 1 1 calc R . . . .
C26 C 0.4546(5) 0.3066(5) 0.9396(4) 0.0406(13) Uani 0.5 1 d . . . G 1
H26A H 0.451808 0.293751 0.980879 0.049 Uiso 0.5 1 calc R . . G 1
H26B H 0.455579 0.360974 0.936812 0.049 Uiso 0.5 1 calc R . . G 1
C26A C 0.4654(5) 0.2480(5) 0.9385(4) 0.0406(13) Uani 0.5 1 d . . . G 2
H26C H 0.465889 0.254168 0.981649 0.049 Uiso 0.5 1 calc R . . G 2
H26D H 0.466006 0.194417 0.930532 0.049 Uiso 0.5 1 calc R . . G 2
O1S O 0.250000 0.2743(3) 0.500000 0.0653(15) Uani 1 2 d S T P . .
H1S H 0.243026 0.289761 0.464033 0.098 Uiso 0.5 1 calc GR . . H -1
C1S C 0.2852(6) 0.1998(5) 0.5068(6) 0.053(2) Uani 0.5 1 d . . . I -1
H1SA H 0.329482 0.196377 0.545673 0.063 Uiso 0.5 1 calc R . . I -1
H1SB H 0.304540 0.188926 0.471858 0.063 Uiso 0.5 1 calc R . . I -1
C2S C 0.2224(7) 0.1467(6) 0.5076(6) 0.060(3) Uani 0.5 1 d . . . I -1
H2SA H 0.177062 0.153859 0.470628 0.090 Uiso 0.5 1 calc GR . . I -1
H2SB H 0.207196 0.155206 0.544467 0.090 Uiso 0.5 1 calc GR . . I -1
H2SC H 0.241891 0.096235 0.508204 0.090 Uiso 0.5 1 calc GR . . I -1
N1A N 0.6203(2) 0.6142(2) 0.76299(17) 0.0444(9) Uani 1 1 d . . . . .
C1A C 0.5426(4) 0.6297(5) 0.7643(4) 0.086(2) Uani 1 1 d . . . . .
H1AA H 0.529431 0.681157 0.752597 0.129 Uiso 1 1 calc GR . . . .
H1AB H 0.540386 0.621228 0.806017 0.129 Uiso 1 1 calc GR . . . .
H1AC H 0.505153 0.597221 0.735168 0.129 Uiso 1 1 calc GR . . . .
C2A C 0.6797(4) 0.6484(4) 0.8191(3) 0.077(2) Uani 1 1 d . . . . .
H2AA H 0.732279 0.641965 0.816218 0.115 Uiso 1 1 calc GR . . . .
H2AB H 0.676637 0.624360 0.856565 0.115 Uiso 1 1 calc GR . . . .
H2AC H 0.668657 0.701116 0.820656 0.115 Uiso 1 1 calc GR . . . .
C3A C 0.6307(4) 0.6523(3) 0.7075(3) 0.0651(15) Uani 1 1 d . . . . .
H3AA H 0.624012 0.705502 0.710870 0.098 Uiso 1 1 calc GR . . . .
H3AB H 0.591601 0.633880 0.669875 0.098 Uiso 1 1 calc GR . . . .
H3AC H 0.683111 0.642145 0.705614 0.098 Uiso 1 1 calc GR . . . .
C4A C 0.6389(5) 0.5371(3) 0.7602(3) 0.081(2) Uani 1 1 d . . . . .
H4AA H 0.596130 0.512476 0.728631 0.121 Uiso 1 1 calc GR . . . .
H4AB H 0.646095 0.514059 0.800385 0.121 Uiso 1 1 calc GR . . . .
H4AC H 0.687129 0.532360 0.749629 0.121 Uiso 1 1 calc GR . . . .
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'
Cl Cl 0.3639 0.7018 '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 0.0520
1 5 -2 0.0542
0 -5 1 0.0477
1 0 -5 0.0390
0 5 -1 0.0510
5 0 -1 0.0473
-1 -5 -1 0.0531
1 5 1 0.0531
-11 0 2 0.0581
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
C26 O1 H1A 109.5 . . ?
C26A O1 H1B 109.5 . . ?
C32 O2 H2B 109.5 . . ?
C32 O2 H2A 109.5 . . ?
C1 N1 H1 126(3) . . ?
C4 N1 H1 123(3) . . ?
C4 N1 C1 111.6(3) . . ?
C6 N2 H2 126(3) . . ?
C9 N2 H2 124(3) . . ?
C9 N2 C6 110.4(3) . . ?
C11 N3 H3 120(3) . . ?
C14 N3 H3 129(3) . . ?
C14 N3 C11 110.7(3) . . ?
C16 N4 H4 122(3) . . ?
C16 N4 C19 109.5(3) . . ?
C19 N4 H4 128(3) . . ?
N1 C1 C20 122.8(3) . . ?
C2 C1 N1 106.2(3) . . ?
C2 C1 C20 131.0(4) . . ?
C1 C2 H2C 126.0 . . ?
C1 C2 C3 108.0(4) . . ?
C3 C2 H2C 126.0 . . ?
C2 C3 H3A 125.8 . . ?
C4 C3 C2 108.5(4) . . ?
C4 C3 H3A 125.8 . . ?
N1 C4 C5 123.2(3) . . ?
C3 C4 N1 105.8(3) . . ?
C3 C4 C5 131.0(4) . . ?
C4 C5 C6 111.3(3) . . ?
C4 C5 C23 108.3(3) . . ?
C4 C5 C24 111.1(3) . . ?
C6 C5 C23 107.9(3) . . ?
C6 C5 C24 108.7(3) . . ?
C23 C5 C24 109.4(3) . . ?
N2 C6 C5 122.7(3) . . ?
C7 C6 N2 106.4(3) . . ?
C7 C6 C5 130.9(3) . . ?
C6 C7 H7 125.7 . . ?
C6 C7 C8 108.5(3) . . ?
C8 C7 H7 125.7 . . ?
C7 C8 H8 126.1 . . ?
C9 C8 C7 107.9(4) . . ?
C9 C8 H8 126.1 . . ?
N2 C9 C10 122.6(3) . . ?
C8 C9 N2 106.8(3) . . ?
C8 C9 C10 130.6(4) . . ?
C9 C10 C11 111.1(3) . . ?
C9 C10 C27 108.6(3) . . ?
C9 C10 C28 110.5(3) . . ?
C11 C10 C27 108.3(3) . . ?
C11 C10 C28 109.6(3) . . ?
C27 C10 C28 108.7(3) . . ?
N3 C11 C10 122.2(3) . . ?
C12 C11 N3 106.8(3) . . ?
C12 C11 C10 131.0(3) . . ?
C11 C12 H12 126.0 . . ?
C11 C12 C13 108.0(3) . . ?
C13 C12 H12 126.0 . . ?
C12 C13 H13 126.1 . . ?
C14 C13 C12 107.9(3) . . ?
C14 C13 H13 126.1 . . ?
N3 C14 C13 106.7(3) . . ?
N3 C14 C15 122.4(3) . . ?
C13 C14 C15 130.9(3) . . ?
C14 C15 C16 110.9(3) . . ?
C14 C15 C29 108.8(3) . . ?
C14 C15 C30 109.8(3) . . ?
C16 C15 C29 108.2(3) . . ?
C16 C15 C30 109.8(3) . . ?
C29 C15 C30 109.3(3) . . ?
N4 C16 C15 122.7(3) . . ?
C17 C16 N4 107.4(3) . . ?
C17 C16 C15 129.9(3) . . ?
C16 C17 H17 126.2 . . ?
C16 C17 C18 107.6(3) . . ?
C18 C17 H17 126.2 . . ?
C17 C18 H18 125.9 . . ?
C19 C18 C17 108.3(3) . . ?
C19 C18 H18 125.9 . . ?
N4 C19 C20 122.5(3) . . ?
C18 C19 N4 107.2(3) . . ?
C18 C19 C20 130.3(3) . . ?
C1 C20 C21 108.2(3) . . ?
C1 C20 C22 109.4(3) . . ?
C19 C20 C1 111.5(3) . . ?
C19 C20 C21 108.8(3) . . ?
C19 C20 C22 110.6(3) . . ?
C21 C20 C22 108.2(3) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C5 C23 H23A 109.5 . . ?
C5 C23 H23B 109.5 . . ?
C5 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C5 C24 H24A 108.0 . . ?
C5 C24 H24B 108.0 . . ?
H24A C24 H24B 107.3 . . ?
C25 C24 C5 117.1(4) . . ?
C25 C24 H24A 108.0 . . ?
C25 C24 H24B 108.0 . . ?
C24 C25 H25A 107.9 . . ?
C24 C25 H25B 107.9 . . ?
C24 C25 H25C 106.3 . . ?
C24 C25 H25D 106.3 . . ?
H25A C25 H25B 107.2 . . ?
H25C C25 H25D 106.4 . . ?
C26 C25 C24 117.5(5) . . ?
C26 C25 H25A 107.9 . . ?
C26 C25 H25B 107.9 . . ?
C26A C25 C24 124.0(6) . . ?
C26A C25 H25C 106.3 . . ?
C26A C25 H25D 106.3 . . ?
C10 C27 H27A 109.5 . . ?
C10 C27 H27B 109.5 . . ?
C10 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C10 C28 H28A 109.5 . . ?
C10 C28 H28B 109.5 . . ?
C10 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C15 C29 H29A 109.5 . . ?
C15 C29 H29B 109.5 . . ?
C15 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C15 C30 H30A 108.7 . . ?
C15 C30 H30B 108.7 . . ?
H30A C30 H30B 107.6 . . ?
C31 C30 C15 114.2(3) . . ?
C31 C30 H30A 108.7 . . ?
C31 C30 H30B 108.7 . . ?
C30 C31 H31A 108.7 . . ?
C30 C31 H31B 108.7 . . ?
H31A C31 H31B 107.6 . . ?
C32 C31 C30 114.3(4) . . ?
C32 C31 H31A 108.7 . . ?
C32 C31 H31B 108.7 . . ?
O2 C32 C31 111.1(4) . . ?
O2 C32 H32A 109.4 . . ?
O2 C32 H32B 109.4 . . ?
C31 C32 H32A 109.4 . . ?
C31 C32 H32B 109.4 . . ?
H32A C32 H32B 108.0 . . ?
O1 C26 C25 114.1(7) . . ?
O1 C26 H26A 108.7 . . ?
O1 C26 H26B 108.7 . . ?
C25 C26 H26A 108.7 . . ?
C25 C26 H26B 108.7 . . ?
H26A C26 H26B 107.6 . . ?
O1 C26A H26C 108.2 . . ?
O1 C26A H26D 108.2 . . ?
C25 C26A O1 116.2(7) . . ?
C25 C26A H26C 108.2 . . ?
C25 C26A H26D 108.2 . . ?
H26C C26A H26D 107.4 . . ?
C1S O1S H1S 109.5 . . ?
O1S C1S H1SA 110.4 . . ?
O1S C1S H1SB 110.4 . . ?
O1S C1S C2S 106.8(8) . . ?
H1SA C1S H1SB 108.6 . . ?
C2S C1S H1SA 110.4 . . ?
C2S C1S H1SB 110.4 . . ?
C1S C2S H2SA 109.5 . . ?
C1S C2S H2SB 109.5 . . ?
C1S C2S H2SC 109.5 . . ?
H2SA C2S H2SB 109.5 . . ?
H2SA C2S H2SC 109.5 . . ?
H2SB C2S H2SC 109.5 . . ?
C1A N1A C2A 109.4(5) . . ?
C1A N1A C3A 108.2(5) . . ?
C1A N1A C4A 115.6(6) . . ?
C3A N1A C2A 106.1(5) . . ?
C4A N1A C2A 108.8(4) . . ?
C4A N1A C3A 108.2(5) . . ?
N1A C1A H1AA 109.5 . . ?
N1A C1A H1AB 109.5 . . ?
N1A C1A H1AC 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
N1A C2A H2AA 109.5 . . ?
N1A C2A H2AB 109.5 . . ?
N1A C2A H2AC 109.5 . . ?
H2AA C2A H2AB 109.5 . . ?
H2AA C2A H2AC 109.5 . . ?
H2AB C2A H2AC 109.5 . . ?
N1A C3A H3AA 109.5 . . ?
N1A C3A H3AB 109.5 . . ?
N1A C3A H3AC 109.5 . . ?
H3AA C3A H3AB 109.5 . . ?
H3AA C3A H3AC 109.5 . . ?
H3AB C3A H3AC 109.5 . . ?
N1A C4A H4AA 109.5 . . ?
N1A C4A H4AB 109.5 . . ?
N1A C4A H4AC 109.5 . . ?
H4AA C4A H4AB 109.5 . . ?
H4AA C4A H4AC 109.5 . . ?
H4AB C4A H4AC 109.5 . . ?
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 H1B 0.8400 . ?
O1 H1A 0.8400 . ?
O1 C26 1.398(9) . ?
O1 C26A 1.561(10) . ?
O2 H2B 0.8400 . ?
O2 H2A 0.8400 . ?
O2 C32 1.423(6) . ?
N1 H1 0.79(5) . ?
N1 C1 1.379(5) . ?
N1 C4 1.375(5) . ?
N2 H2 0.89(5) . ?
N2 C6 1.387(4) . ?
N2 C9 1.381(5) . ?
N3 H3 0.86(5) . ?
N3 C11 1.379(5) . ?
N3 C14 1.377(5) . ?
N4 H4 0.93(5) . ?
N4 C16 1.379(5) . ?
N4 C19 1.390(5) . ?
C1 C2 1.368(5) . ?
C1 C20 1.512(5) . ?
C2 H2C 0.9500 . ?
C2 C3 1.421(6) . ?
C3 H3A 0.9500 . ?
C3 C4 1.373(6) . ?
C4 C5 1.507(5) . ?
C5 C6 1.519(6) . ?
C5 C23 1.540(5) . ?
C5 C24 1.560(5) . ?
C6 C7 1.367(6) . ?
C7 H7 0.9500 . ?
C7 C8 1.418(6) . ?
C8 H8 0.9500 . ?
C8 C9 1.372(5) . ?
C9 C10 1.513(5) . ?
C10 C11 1.517(5) . ?
C10 C27 1.540(5) . ?
C10 C28 1.542(5) . ?
C11 C12 1.378(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.417(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.382(5) . ?
C14 C15 1.510(5) . ?
C15 C16 1.521(5) . ?
C15 C29 1.536(5) . ?
C15 C30 1.561(5) . ?
C16 C17 1.375(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.419(6) . ?
C18 H18 0.9500 . ?
C18 C19 1.364(5) . ?
C19 C20 1.511(5) . ?
C20 C21 1.531(5) . ?
C20 C22 1.547(5) . ?
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 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.527(6) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 H25C 0.9900 . ?
C25 H25D 0.9900 . ?
C25 C26 1.503(10) . ?
C25 C26A 1.303(10) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C30 C31 1.526(5) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.511(7) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26A H26C 0.9900 . ?
C26A H26D 0.9900 . ?
O1S H1S 0.8400 . ?
O1S C1S 1.481(10) . ?
C1S H1SA 0.9900 . ?
C1S H1SB 0.9900 . ?
C1S C2S 1.492(13) . ?
C2S H2SA 0.9800 . ?
C2S H2SB 0.9800 . ?
C2S H2SC 0.9800 . ?
N1A C1A 1.442(7) . ?
N1A C2A 1.518(7) . ?
N1A C3A 1.510(7) . ?
N1A C4A 1.446(7) . ?
C1A H1AA 0.9800 . ?
C1A H1AB 0.9800 . ?
C1A H1AC 0.9800 . ?
C2A H2AA 0.9800 . ?
C2A H2AB 0.9800 . ?
C2A H2AC 0.9800 . ?
C3A H3AA 0.9800 . ?
C3A H3AB 0.9800 . ?
C3A H3AC 0.9800 . ?
C4A H4AA 0.9800 . ?
C4A H4AB 0.9800 . ?
C4A H4AC 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
O1 H1B Cl1 0.84 2.62 3.407(4) 156.4 . yes
O1 H1A O2 0.84 2.02 2.795(5) 152.9 7_556 yes
O2 H2B O1 0.84 2.01 2.795(5) 155.0 7_556 yes
O2 H2A O1S 0.84 1.89 2.720(4) 168.6 . yes
N1 H1 Cl1 0.79(5) 2.54(5) 3.326(3) 176(5) . yes
N2 H2 Cl1 0.89(5) 2.44(5) 3.334(3) 177(4) . yes
N3 H3 Cl1 0.86(5) 2.53(5) 3.380(3) 170(5) . yes
N4 H4 Cl1 0.93(5) 2.39(5) 3.317(3) 175(4) . yes
