Capture and displacement-based release of the bicarbonate anion by calix[4]pyrroles with small rigid straps
Heo, Nam Jung; Sessler, Jonathan L.; Ko, Byoung Joon; Kim, Sung Kuk; Yang, Ju Ho; Lynch, Vincent; Chemical Science  (2020) –; doi:10.1039/D0SC03445B

data_1558665
_publ_section_title
;
 Capture and displacement-based release of the bicarbonate anion by
 calix[4]pyrroles with small rigid straps
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC03445B
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C O3, C45 H45 N5 O2, C8 H20 N'
_chemical_formula_sum            'C54 H65 N6 O5'
_chemical_formula_weight         878.12
_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_Hall           'P 4abw 2nw'
_space_group_name_H-M_alt        'P 41 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-03-26
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-06-18 deposited with the CCDC.	2020-07-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.3125(2)
_cell_length_b                   15.3125(2)
_cell_length_c                   23.8680(4)
_cell_measurement_reflns_used    2719
_cell_measurement_temperature    100.01(11)
_cell_measurement_theta_max      72.8890
_cell_measurement_theta_min      3.3930
_cell_volume                     5596.39(14)
_computing_cell_refinement       'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2940
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.986
_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   -114.00 -14.00   1.00    4.00    --  -41.72 -57.00 150.00  100
  2  \w    114.00 154.00   1.00   12.50    --  107.09  77.00 150.00   40
  3  \w     38.00  99.00   1.00   12.50    --  107.09-125.00-180.00   61
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0222008000
_diffrn_orient_matrix_UB_12      -0.0298011000
_diffrn_orient_matrix_UB_13      0.0599796000
_diffrn_orient_matrix_UB_21      0.0687293000
_diffrn_orient_matrix_UB_22      0.0636576000
_diffrn_orient_matrix_UB_23      0.0235065000
_diffrn_orient_matrix_UB_31      -0.0700588000
_diffrn_orient_matrix_UB_32      0.0719504000
_diffrn_orient_matrix_UB_33      0.0039918000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10560
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.218
_diffrn_reflns_theta_min         3.429
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.533
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.566
_exptl_absorpt_correction_type   multi-scan
_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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.042
_exptl_crystal_description       plate
_exptl_crystal_F_000             1884
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.068
_refine_diff_density_max         0.628
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details
;
 Flack x determined using 1752 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.4(2)
_refine_ls_extinction_coef       0.0014(4)
_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   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     394
_refine_ls_number_reflns         5480
_refine_ls_number_restraints     122
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0891
_refine_ls_R_factor_gt           0.0802
_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/[\s^2^(Fo^2^)+(0.1733P)^2^+3.0124P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2419
_refine_ls_wR_factor_ref         0.2557
_reflns_Friedel_coverage         0.716
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                4758
_reflns_number_total             5480
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc03445b2.cif
_cod_data_source_block           hnj2
_cod_original_cell_volume        5596.37(19)
_cod_database_code               1558665
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C32H24N4O4
_shelx_estimated_absorpt_t_max   0.965
_shelx_estimated_absorpt_t_min   0.827
_reflns_odcompleteness_completeness 86.47
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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
2. Restrained distances
 N4-C22
 1.35 with sigma of 0.02
 N4-C21
 2.4 with sigma of 0.03
 C21-C22
 1.4 with sigma of 0.02
 C18-C20
 2.4 with sigma of 0.03
 C21-C20
 1.4 with sigma of 0.02
 C21-C19
 2.4 with sigma of 0.03
 C20-C19
 1.4 with sigma of 0.02
 C20-C18
 2.4 with sigma of 0.03
 C19-C18
 1.4 with sigma of 0.02
 C20-C22
 2.4 with sigma of 0.03
 C18-N4
 1.35 with sigma of 0.02
 N4-C19
 2.4 with sigma of 0.03
 N4-C20
 2.8 with sigma of 0.03
 C22-C19
 2.8 with sigma of 0.03
 C18-C21
 2.8 with sigma of 0.03
 C17-C18 = C17A-C18A
 1.5 with sigma of 0.03
 O1-C17 = O1-C17A
 1.4 with sigma of 0.02
 O2-C30
 1.22 with sigma of 0.02
 O3-C30 = O3A-C30
 1.3 with sigma of 0.01
 C17A-C19A \\sim C17A-N4A
 with sigma of 0.01
 O2-O3 \\sim O2-O3A
 with sigma of 0.01
3. Restrained planarity
 N4A, C17A, C18A, C19A, C20A, C21A, C22A
 with sigma of 0.01
 N4, C21, C22, C20, C19, C18, C17
 with sigma of 0.01
 O2, O3, O3A, C30
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
N4 \\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim C22: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02 within 2A
C18A \\sim C19A \\sim C20A \\sim C21A \\sim C22A \\sim N4A: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
C18 \\sim C19 \\sim C20 \\sim C21 \\sim C22 \\sim N4: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02 within 2A
O3 \\sim C30 \\sim O3A \\sim O2: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
Uanis(C17) = Uanis(C17A)
Uanis(O1) = Uanis(O1A)
Uanis(O1A) = Uanis(O1)
Uanis(N4A) = Uanis(N4)
Uanis(C18A) = Uanis(C18)
5. Others
 Sof(C17A)=Sof(H17C)=Sof(H17D)=Sof(O1A)=1-FVAR(1)
 Sof(N4A)=Sof(C18A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(H20A)=Sof(C21A)=
 Sof(H21A)=Sof(C22A)=0.5*(1-FVAR(2))
 Sof(N4)=Sof(C18)=Sof(C19)=Sof(H19)=Sof(C20)=Sof(H20)=Sof(C21)=Sof(H21)=
 Sof(C22)=0.5*FVAR(2)
 Sof(O1)=Sof(C17)=Sof(H17A)=Sof(H17B)=FVAR(1)
 Fixed Sof: O2(0.5) O3(0.5) O3A(0.5) C30(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C17A(H17C,H17D), C28(H28A,H28B), C26(H26A,H26B)
6.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C20(H20), C21(H21), C19A(H19A), C20A(H20A), C21A(H21A), N1(H1),
 N2(H2), C2(H2A), C3(H3), C7(H7), C8(H8), C12(H12), C13(H13), C15(H15), C16(H16)
6.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C27(H27A,H27B,
 H27C), C29(H29A,H29B,H29C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              24838
_shelx_fab_checksum              44461
_olex2_date_sample_data_collection 2020-03-24
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.309
_oxdiff_exptl_absorpt_empirical_full_min 0.793