Anion binding and transport with <i>meso</i>-alkyl substituted two-armed calix[4]pyrroles bearing urea and hydroxyl groups.
Pamuła, Małgorzata; Bulatov, Evgeny; Martínez-Crespo, Luis; Kiesilä, Anniina; Naulapää, Julia; Kalenius, Elina; Helttunen, Kaisa; Organic & biomolecular chemistry 21 (2023) 6595–6603; doi:10.1039/d3ob00919j

data_7159506
_publ_section_title
;
 Anion binding and transport with <i>meso</i>-alkyl substituted two-armed
 calix[4]pyrroles bearing urea and hydroxyl groups.
;
_journal_issue                   32
_journal_name_full               'Organic &amp; 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  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -110.00 -24.00   1.00    6.00    --  -41.92 -37.00-150.00   86
  2  \w   -114.00 -19.00   1.00    6.00    --  -41.92 -37.00 120.00   95
  3  \w    -86.00 -54.00   1.00    6.00    --  -41.92 125.00  30.00   32
  4  \w     55.00  82.00   1.00    6.00    --   41.92-122.00 137.00   27
  5  \w     36.00 109.00   1.00   30.00    --  112.00-111.00-180.00   73
  6  \w     59.00 109.00   1.00   30.00    --  112.00-111.00-150.00   50
  7  \w     87.00 139.00   1.00   30.00    --  112.00 178.00 -30.00   52
  8  \w     60.00 177.00   1.00   30.00    --  112.00  15.00 -30.00  117
  9  \w    103.00 177.00   1.00   30.00    --  112.00  30.00  30.00   74
 10  \w     83.00 109.00   1.00   30.00    --  112.00-111.00 120.00   26
 11  \w     52.00  91.00   1.00   30.00    --  112.00 -45.00 -60.00   39
 12  \w    111.00 138.00   1.00   30.00    --  112.00 -45.00 -60.00   27
 13  \w     83.00 134.00   1.00   30.00    --  112.00 178.00-150.00   51
 14  \w     36.00  76.00   1.00   30.00    --  112.00-111.00-120.00   40
 15  \w     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       '\w 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+0.001xFc^2^\l^3^/sin(2\q)]^-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/[\s^2^(Fo^2^)+(0.0617P)^2^+42.9873P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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_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)
;
_shelx_res_checksum              36929
_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
;