Hemispherand-Strapped Calix[4]pyrrole: An Ion-pair Receptor for the Recognition and Extraction of Lithium Nitrite.
He, Qing; Zhang, Zhan; Brewster, James T.; Lynch, Vincent M.; Kim, Sung Kuk; Sessler, Jonathan L.; Journal of the American Chemical Society 138 (2016) 9779–9782; doi:10.1021/jacs.6b05713

data_4130671
_publ_section_title
;
 Hemispherand-Strapped Calix[4]pyrrole: An Ion-pair Receptor for the
 Recognition and Extraction of Lithium Nitrite.
;
_journal_issue                   31
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9779
_journal_page_last               9782
_journal_paper_doi               10.1021/jacs.6b05713
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C50 H56 Li N9 O6, 3(C2 H3 N)'
_chemical_formula_sum            'C56 H65 Li N12 O6'
_chemical_formula_weight         1009.14
_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     direct
_audit_creation_date             2016-06-03
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                86.6932(19)
_cell_angle_beta                 83.3607(19)
_cell_angle_gamma                69.639(2)
_cell_formula_units_Z            2
_cell_length_a                   13.8350(3)
_cell_length_b                   13.9110(3)
_cell_length_c                   14.7899(3)
_cell_measurement_reflns_used    36551
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4340
_cell_measurement_theta_min      2.9990
_cell_volume                     2650.23(10)
_computing_cell_refinement       'CrysAlisPro 1.171.38.27t (Agilent, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.27t (Agilent, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.27t (Agilent, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2940
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_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    -65.00  33.00   1.00    1.00    --  -40.84  38.00 -90.00   98
  2  \w   -115.00 -16.00   1.00    1.00    --  -40.84 -38.00  90.00   99
  3  \w    -65.00  33.00   1.00    1.00    --  -40.84  38.00  30.00   98
  4  \w     23.00  97.00   1.00    1.00    --   40.84-125.00  30.00   74
  5  \w     34.00 122.00   1.00    3.00    --  106.76-125.00  60.00   88
  6  \w     24.00 109.00   1.00    3.00    --  106.76 -94.00-180.00   85
  7  \w     94.00 178.00   1.00    3.00    --  106.76 125.00-180.00   84
  8  \w     30.00 135.00   1.00    3.00    --  106.76 -30.00 120.00  105
  9  \w     24.00 109.00   1.00    3.00    --  106.76 -94.00  90.00   85
 10  \w     81.00 178.00   1.00    3.00    --  106.76  45.00-180.00   97
 11  \w     81.00 178.00   1.00    3.00    --  106.76  45.00 -60.00   97
 12  \w     34.00 136.00   1.00    3.00    --  106.76 -61.00-150.00  102
 13  \w     30.00 135.00   1.00    3.00    --  106.76 -30.00-120.00  105
 14  \w     74.00 178.00   1.00    3.00    --  106.76  77.00-120.00  104
 15  \w   -114.00 -13.00   1.00    1.00    --  -40.84 -57.00   0.00  101
 16  \w   -117.00  -8.00   1.00    1.00    --  -40.84 -77.00 -90.00  109
 17  \w      8.00 117.00   1.00    1.00    --   40.84  77.00-150.00  109
 18  \w      1.00  82.00   1.00    1.00    --   40.84 -99.00 120.00   81
 19  \w     78.00 178.00   1.00    3.00    --  106.76  61.00 150.00  100
 20  \w     78.00 178.00   1.00    3.00    --  106.76  61.00 120.00  100
 21  \w     74.00 178.00   1.00    3.00    --  106.76  77.00 -30.00  104
 22  \w     74.00 178.00   1.00    3.00    --  106.76  77.00 -60.00  104
 23  \w     54.00 178.00   1.00    3.00    --  106.76  15.00  90.00  124
 24  \w     74.00 178.00   1.00    3.00    --  106.76  77.00  30.00  104
 25  \w     74.00 178.00   1.00    3.00    --  106.76  77.00  60.00  104
 26  \w     78.00 178.00   1.00    3.00    --  106.76  61.00-150.00  100
 27  \w   -117.00  -8.00   1.00    1.00    --  -40.84 -77.00 -30.00  109
 28  \w   -117.00  -8.00   1.00    1.00    --  -40.84 -77.00-180.00  109
 29  \w   -115.00 -16.00   1.00    1.00    --  -40.84 -38.00-120.00   99
 30  \w      8.00 117.00   1.00    1.00    --   40.84  77.00 120.00  109
 31  \w     74.00 144.00   1.00    3.00    --  106.76  77.00   0.00   70
 32  \w     74.00 178.00   1.00    3.00    --  106.76  77.00  90.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0382440000
_diffrn_orient_matrix_UB_12      0.0979252000
_diffrn_orient_matrix_UB_13      -0.0593222000
_diffrn_orient_matrix_UB_21      -0.0354136000
_diffrn_orient_matrix_UB_22      -0.0590084000
_diffrn_orient_matrix_UB_23      -0.0667392000
_diffrn_orient_matrix_UB_31      -0.1074192000
_diffrn_orient_matrix_UB_32      0.0297818000
_diffrn_orient_matrix_UB_33      0.0550238000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            49679
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.504
_diffrn_reflns_theta_min         3.009
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.678
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62205
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.27t (Agilent, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.206
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.101
_refine_diff_density_max         0.734
_refine_diff_density_min         -0.649
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     690
_refine_ls_number_reflns         10482
_refine_ls_number_restraints     453
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0416
_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^)+(0.0510P)^2^+1.4490P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1054
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10030
_reflns_number_total             10482
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b05713_si_006.cif
_cod_data_source_block           hq-2n-calixpyr-lino2
_cod_original_cell_volume        2650.24(11)
_cod_database_code               4130671
_chemical_oxdiff_formula         C35H50N6O8Li1
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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, All O(H) groups
2. Restrained distances
 O6-H6
 0.87 with sigma of 0.01
 C50-H6
 1.897416 with sigma of 0.02
 Li23-H6
 2.537507 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.1 and sigma
for terminal atoms of 0.2
4.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C42(H42A,H42B), C41(H41A,H41B), C22(H22A,H22B)
4.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), N2(H2), N4(H4), N8(H8), N5(H5), C8(H8A), C9(H9), C4(H4A),
 C30(H30), C32(H32), C31(H31), C3(H3A), C27(H27), C25(H25), C13(H13), C36(H36),
 C14(H14), C19(H19), C18(H18), C26(H26), C38(H38), C37(H37)
4.c Idealised Me refined as rotating group:
 C48(H48A,H48B,H48C), C47(H47A,H47B,H47C), C45(H45A,H45B,H45C), C46(H46A,H46B,
 H46C), C43(H43A,H43B,H43C), C44(H44A,H44B,H44C), C50(H50A,H50B,H50C), C54(H54A,
 H54B,H54C), C49(H49A,H49B,H49C), C56(H56A,H56B,H56C), C52(H52A,H52B,H52C)
;
_shelx_res_checksum              31002
_shelx_hkl_checksum              83035
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-03-05
_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 1.583
_oxdiff_exptl_absorpt_empirical_full_min 0.634