Neutral iodotriazole foldamers as tetradentate halogen bonding anion receptors.
Borissov, Arseni; Lim, Jason Y. C.; Brown, Asha; Christensen, Kirsten E.; Thompson, Amber L.; Smith, Martin D.; Beer, Paul D.; Chemical communications (Cambridge, England) 53 (2017) 2483–2486; doi:10.1039/c7cc00727b

data_7119623
_publ_section_title
;
 Neutral iodotriazole foldamers as tetradentate halogen bonding anion
 receptors.
;
_journal_issue                   16
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              2483
_journal_page_last               2486
_journal_paper_doi               10.1039/c7cc00727b
_journal_volume                  53
_journal_year                    2017
_chemical_formula_moiety         'C134 H108 I8 N24 Na2 O12, 2(I), 6(C3 H6 O)'
_chemical_formula_sum            'C152 H144 I10 N24 Na2 O18'
_chemical_formula_weight         3909.98
_chemical_melting_point          ?
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             01-11-16
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2017-01-24 deposited with the CCDC.
2017-02-06 downloaded from the CCDC.
;
_cell_angle_alpha                113.335(2)
_cell_angle_beta                 100.303(2)
_cell_angle_gamma                93.903(2)
_cell_formula_units_Z            1
_cell_length_a                   14.3220(4)
_cell_length_b                   17.7665(5)
_cell_length_c                   17.7815(5)
_cell_measurement_reflns_used    18398
_cell_measurement_temperature    100
_cell_measurement_theta_max      36
_cell_measurement_theta_min      2
_cell_volume                     4038.8(2)
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_collection       'Diamond GDA'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.872
_diffrn_measurement_device
'Pilatus 2M detector on Crystal Logic diffractometer'
_diffrn_measurement_device_type  'Photon counting area detector'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_radiation_monochromator  Synchrotron
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.68890
_diffrn_reflns_av_R_equivalents  0.195
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            88130
_diffrn_reflns_theta_full        25.140
_diffrn_reflns_theta_max         36.434
_diffrn_reflns_theta_min         1.661
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.991
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.04
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            clear_pale_yellow
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1920
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform, acetone'
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_platon_squeeze_details
;
The discrete Fourier transform of the void region were treated as 
contributions to the A and B parts of the calculated structure factors.
;
_refine_diff_density_max         2.38
_refine_diff_density_min         -3.28
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9962
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     928
_refine_ls_number_reflns         14420
_refine_ls_number_restraints     955
_refine_ls_R_factor_all          0.1180
_refine_ls_R_factor_gt           0.0996
_refine_ls_shift/su_max          0.0065118
_refine_ls_shift/su_mean         0.0002438
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.20P)^2^ + 0.00P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2929
_refine_ls_wR_factor_gt          0.2809
_refine_ls_wR_factor_ref         0.2929
_reflns_limit_h_max              23
_reflns_limit_h_min              -24
_reflns_limit_k_max              28
_reflns_limit_k_min              -29
_reflns_limit_l_max              30
_reflns_limit_l_min              0
_reflns_number_gt                9220
_reflns_number_total             37810
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   4.77
_oxford_diffrn_Wilson_scale      0.28
_oxford_refine_ls_r_factor_ref   0.1180
_oxford_refine_ls_scale          1.462(12)
_oxford_reflns_number_all        14420
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title '037ab16 (6626)'
_cod_data_source_file            c7cc00727b2.cif
_cod_data_source_block           3b_NaI
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

'_atom_sites_solution_primary' value 'Other' changed to 'other'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7119623.cif.

2024-04-09
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_weight         1954.99
_cod_original_formula_moiety         'C64 H48 I5 N12 Na1 O5, 4(C3 H6 O1)'
_cod_original_formula_units_Z            2
_cod_original_sg_symbol_Hall     -P1
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C76 H72 I5 N12 Na1 O9'
_cod_database_code               7119623
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) H   ( 152,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
RIDE C   (  35,X'S) H   ( 351,X'S) 
RIDE C   (  37,X'S) H   ( 371,X'S) 
RIDE C   (  39,X'S) H   ( 391,X'S) 
RIDE C   (  47,X'S) H   ( 471,X'S) 
RIDE C   (  48,X'S) H   ( 481,X'S) 
RIDE C   (  49,X'S) H   ( 491,X'S) 
RIDE C   (  51,X'S) H   ( 511,X'S) 
RIDE C   (  58,X'S) H   ( 581,X'S) H   ( 582,X'S) 
RIDE C   (  61,X'S) H   ( 611,X'S) 
RIDE C   (  62,X'S) H   ( 621,X'S) 
RIDE C   (  63,X'S) H   ( 631,X'S) 
RIDE C   (  64,X'S) H   ( 641,X'S) 
RIDE C   (  66,X'S) H   ( 661,X'S) 
RIDE C   (  68,X'S) H   ( 681,X'S) 
RIDE C   (  69,X'S) H   ( 691,X'S) 
RIDE C   (  70,X'S) H   ( 701,X'S) 
RIDE C   (  71,X'S) H   ( 711,X'S) 
RIDE C   (  76,X'S) H   ( 761,X'S) H   ( 762,X'S) 
RIDE C   (  77,X'S) H   ( 771,X'S) H   ( 772,X'S) 
RIDE C   (  79,X'S) H   ( 791,X'S) H   ( 792,X'S) 
RIDE C   (  80,X'S) H   ( 801,X'S) H   ( 802,X'S) 
RIDE C   (  82,X'S) H   ( 821,X'S) H   ( 822,X'S) 
RIDE C   (  83,X'S) H   ( 831,X'S) H   ( 832,X'S) 
RIDE C   (  85,X'S) H   ( 851,X'S) H   ( 852,X'S) H   ( 853,X'S) 
RIDE C   (  90,X'S) H   ( 901,X'S) H   ( 902,X'S) H   ( 903,X'S) 
RIDE C   (  91,X'S) H   ( 911,X'S) H   ( 912,X'S) H   ( 913,X'S) 
RIDE C   (  94,X'S) H   ( 941,X'S) H   ( 942,X'S) H   ( 943,X'S) 
RIDE C   (  95,X'S) H   ( 951,X'S) H   ( 952,X'S) H   ( 953,X'S) 
RIDE C   (  98,X'S) H   ( 981,X'S) H   ( 982,X'S) H   ( 983,X'S) 
RIDE C   (  99,X'S) H   ( 991,X'S) H   ( 992,X'S) H   ( 993,X'S) 
RIDE C   ( 100,X'S) H   (1001,X'S) H   (1002,X'S) H   (1003,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
REM ACETONE MOLECULES 
PLANAR C(100) UNTIL C(103) 
PLANAR O(96) UNTIL C(99) 
PLANAR O(92) UNTIL C(95) 
DISTANCE 1.22, 0.01 = C(101) TO O(102) 
CONT O(96) TO C(97) O(92) TO C(93) 
DISTANCE 1.52, 0.001 = C(97) TO C(98) 
CONT C(97) TO C(99) C(93) TO C(94) 
CONT C(93) TO C(95) C(100) TO C(101) 
CONT C(101) TO C(103) 
ANGLE 116,2 = C(94) TO C(93) TO C(95) 
CONT C(100) TO C(101) TO C(103) 
CONT C(98) TO C(97) TO C(99) 
ANGLE 122,2 = O(92) TO C(93) TO C(94) 
CONT O(92) TO C(93) TO C(95) 
CONT C(98) TO C(97) TO O(96) 
CONT C(99) TO C(97) TO O(96) 
CONT C(100) TO C(101) TO O(102) 
CONT C(103) TO C(101) TO O(102) 
SIMU 0.04 C(90) C(89) C(91) 
DELU 0.01 C(90) C(89) C(91) 
SIMU 0.04 C(98) C(97) C(99) 
SIMU 0.04 C(97) O(96) 
DELU 0.01 C(98) C(97) C(99) 
DELU 0.01 C(97) O(96) 
SIMU 0.04 C(100) C(101) C(103) 
SIMU 0.04 C(101) O(102) 
DELU 0.01 C(100) C(101) C(103) 
DELU 0.01  C(101) O(102) 
SIMU 0.04 C(94) C(93) C(95) 
SIMU 0.04 C(93) O(92) 
DELU 0.01 C(94) C(93) C(95) 
DELU 0.01 C(93) O(92) 
SAME C(90) C(89) C(91) AND 
CONT C(91) C(89) C(90) 
SIMU 0.04 C(90) C(89) C(91) 
SIMU 0.04 C(89) O(88) 
SIMU 0.01 C(90) C(89) C(91) 
SIMU 0.01 C(89) O(88) 
REM PHENYL GROUPS 
DIST 0.0, 0.01 = MEAN C(22) TO C(23) 
CONT C(23) TO C(24) C(24) TO C(25) 
CONT C(25) TO C(26) C(26) TO C(27) 
CONT C(27) TO C(22) C(46) TO C(47) 
CONT C(47) TO C(48) C(48) TO C(49) 
CONT C(49) TO C(50) C(50) TO C(51) 
CONT C(51) TO C(46) 
DIST 0.0, 0.01 = MEAN C(34) TO C(35) 
CONT C(35) TO C(36) C(36) TO C(37) 
CONT C(37) TO C(38) C(38) TO C(39) 
CONT C(39) TO C(34) 
DELU 0.01 C(43) C(46) C(47) C(48) C(49) C(50) C(51) 
REM TRIAZOLES 
SAME C(15) N(16) N(17) N(18) C(19) C(20) AND 
CONT C(58) N(55) N(54) N(53) C(52) C(56) 
SAME C(28) N(29) N(30) N(31) C(32) AND 
CONT C(43) N(42) N(41) N(40) C(44) 
SIMU 0.04 N(40) N(41) N(42) C(43) C(44) 
DELU 0.01 N(40) N(41) N(42) C(43) C(44) 
SIMU 0.04 C(52) N(53) N(54) N(55) C(56) 
DELU 0.01 C(52) N(53) N(54) N(55) C(56) 
REM ANTHRACENES 
SAME C(15) C(14) C(13) C(12) C(11) C(10) 
CONT C(9) C(8) C(7) C(6) C(5) C(4) C(3) 
CONT C(2) C(1) AND 
CONT C(15) C(14) C(1) C(2) C(3) C(4) C(5) 
CONT C(6) C(7) C(8) C(9) C(10) C(11) C(12) 
CONT C(13) AND 
CONT C(58) C(59) C(60) C(61) C(62) C(63) 
CONT C(64) C(65) C(66) C(67) C(68) C(69) 
CONT C(70) C(71) C(72) AND 
CONT C(58) C(59) C(72) C(71) C(70) C(69) 
CONT C(68) C(67) C(66) C(65) C(64) C(63) 
CONT C(62) C(61) C(60) 
SIMU 0.02 C(1) C(2) C(3) C(4) C(5) C(6) 
CONT C(7) C(8) C(9) C(10) C(11) C(12) 
CONT C(13) C(14) C(15) 
DELU 0.005 C(1) C(2) C(3) C(4) C(5) C(6) 
CONT C(7) C(8) C(9) C(10) C(11) C(12) 
CONT C(13) C(14) C(15) 
SIMU 0.02 C(58) C(59) C(60) C(61) C(62) C(63) 
CONT C(64) C(65) C(66) C(67) C(68) C(69) 
CONT C(70) C(71) C(72) 
DELU 0.005 C(58) C(59) C(60) C(61) C(62) C(63) 
CONT C(64) C(65) C(66) C(67) C(68) C(69) 
CONT C(70) C(71) C(72) 
REM POLYETHER 
SAME O(75) C(76) C(77) O(78) C(79) C(80) 
CONT O(81) C(82) C(83) O(84) AND 
CONT O(84) C(83) C(82) O(81) C(80) C(79) 
CONT O(78) C(77) C(76) O(75) 
SIMU 0.04 O(75) C(76) C(77) O(78) C(79) C(80) 
CONT O(81) C(82) C(83) O(84) C(85) 
DELU 0.01 O(75) C(76) C(77) O(78) C(79) C(80) 
CONT O(81) C(82) C(83) O(84) C(85) 
REM MISCELLANEOUS 
DISTANCE 0.0, 0.01 = MEAN C(19) TO C(22) 
CONT C(52) TO C(50) 
DISTANCE 0.0, 0.01 = MEAN C(26) TO C(28) 
CONT C(46) TO C(43) 
REM   DELU   START (DO NOT REMOVE THIS LINE) 
VIBR .0, 0.00200 = O(75) TO NA(86) 
VIBR .0, 0.00500 = NA(86) TO C(73) 
VIBR .0, 0.00500 = NA(86) TO C(76) 
VIBR .0, 0.00200 = O(78) TO NA(86) 
VIBR .0, 0.00500 = NA(86) TO C(77) 
VIBR .0, 0.00500 = NA(86) TO C(79) 
VIBR .0, 0.00200 = O(81) TO NA(86) 
VIBR .0, 0.00500 = NA(86) TO C(80) 
VIBR .0, 0.00500 = NA(86) TO C(82) 
VIBR .0, 0.00200 = O(84) TO NA(86) 
VIBR .0, 0.00500 = NA(86) TO C(83) 
VIBR .0, 0.00500 = NA(86) TO C(85) 
VIBR .0, 0.00200 = NA(86) TO O(88) 
VIBR .0, 0.00500 = O(78) TO O(81) 
VIBR .0, 0.00500 = O(84) TO O(81) 
VIBR .0, 0.00500 = O(84) TO O(78) 
VIBR .0, 0.00500 = N(18,-1,1,2,2) TO O(81) 
VIBR .0, 0.00500 = N(18,-1,1,2,2) TO O(78) 
VIBR .0, 0.00500 = N(18,-1,1,2,2) TO O(84) 
VIBR .0, 0.00500 = O(75) TO O(81) 
VIBR .0, 0.00500 = O(75) TO O(78) 
VIBR .0, 0.00500 = O(75) TO O(84) 
VIBR .0, 0.00500 = O(75) TO N(18,-1,1,2,2) 
VIBR .0, 0.00500 = O(88) TO O(81) 
VIBR .0, 0.00500 = O(88) TO O(78) 
VIBR .0, 0.00500 = O(88) TO O(84) 
VIBR .0, 0.00500 = O(88) TO N(18,-1,1,2,2) 
VIBR .0, 0.00500 = O(88) TO O(75) 
VIBR .0, 0.00200 = O(88) TO C(89) 
VIBR .0, 0.00500 = C(89) TO NA(86) 
VIBR .0, 0.00200 = C(89) TO C(90) 
VIBR .0, 0.00200 = C(89) TO C(91) 
VIBR .0, 0.00500 = C(90) TO O(88) 
VIBR .0, 0.00500 = C(91) TO O(88) 
VIBR .0, 0.00500 = C(91) TO C(90) 
VIBR .0, 0.00200 = O(92) TO C(93) 
VIBR .0, 0.00200 = C(93) TO C(94) 
VIBR .0, 0.00200 = C(93) TO C(95) 
VIBR .0, 0.00500 = C(94) TO O(92) 
VIBR .0, 0.00500 = C(95) TO O(92) 
VIBR .0, 0.00500 = C(95) TO C(94) 
VIBR .0, 0.00200 = O(96) TO C(97) 
VIBR .0, 0.00200 = C(97) TO C(98) 
VIBR .0, 0.00200 = C(97) TO C(99) 
VIBR .0, 0.00500 = C(98) TO O(96) 
VIBR .0, 0.00500 = C(99) TO O(96) 
VIBR .0, 0.00500 = C(99) TO C(98) 
VIBR .0, 0.00200 = C(100) TO C(101) 
VIBR .0, 0.00200 = C(101) TO O(102) 
VIBR .0, 0.00200 = C(101) TO C(103) 
VIBR .0, 0.00500 = O(102) TO C(100) 
VIBR .0, 0.00500 = C(103) TO C(100) 
VIBR .0, 0.00500 = C(103) TO O(102) 
REM   DELU   END (DO NOT REMOVE THIS LINE) 
REM   THERMSIM   START (DO NOT REMOVE THIS LINE) 
U(IJ) .0, 0.02000 = O(75) TO NA(86) 
U(IJ) .0, 0.02000 = O(78) TO NA(86) 
U(IJ) .0, 0.02000 = O(81) TO NA(86) 
U(IJ) .0, 0.02000 = O(84) TO NA(86) 
U(IJ) .0, 0.04000 = NA(86) TO O(88) 
U(IJ) .0, 0.04000 = O(88) TO C(89) 
U(IJ) .0, 0.08000 = C(89) TO C(90) 
U(IJ) .0, 0.08000 = C(89) TO C(91) 
U(IJ) .0, 0.04000 = O(92) TO C(93) 
U(IJ) .0, 0.04000 = C(93) TO C(94) 
U(IJ) .0, 0.04000 = C(93) TO C(95) 
U(IJ) .0, 0.04000 = O(96) TO C(97) 
U(IJ) .0, 0.04000 = C(97) TO C(98) 
U(IJ) .0, 0.04000 = C(97) TO C(99) 
U(IJ) .0, 0.04000 = C(100) TO C(101) 
U(IJ) .0, 0.04000 = C(101) TO O(102) 
U(IJ) .0, 0.04000 = C(101) TO C(103) 
REM   THERMSIM   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;