A pentagonal cyanostar macrocycle with cyanostilbene CH donors binds anions and forms dialkylphosphate [3]rotaxanes
Semin Lee; Chun-Hsing Chen; Amar H. Flood; Nature Chemistry 5 (2013) 704–710; doi:10.1038/nchem.1668

data_1551390
_publ_section_title
;
 A pentagonal cyanostar macrocycle with cyanostilbene CH donors binds
 anions and forms dialkylphosphate [3]rotaxanes
;
_journal_name_full               'Nature Chemistry'
_journal_page_first              704
_journal_page_last               710
_journal_paper_doi               10.1038/nchem.1668
_journal_volume                  5
_journal_year                    2013
_chemical_absolute_configuration .
_chemical_formula_moiety         'C65 H65.00 N5'
_chemical_formula_sum            'C65 H65 N5'
_chemical_formula_weight         916.26
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                103.495(2)
_cell_angle_beta                 103.098(2)
_cell_angle_gamma                102.405(3)
_cell_formula_units_Z            2
_cell_length_a                   13.520(2)
_cell_length_b                   14.217(2)
_cell_length_c                   17.557(3)
_cell_measurement_reflns_used    8150
_cell_measurement_temperature    150
_cell_measurement_theta_max      24
_cell_measurement_theta_min      2
_cell_volume                     3065.8(8)
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_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    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            16876
_diffrn_reflns_theta_full        25.239
_diffrn_reflns_theta_max         30.047
_diffrn_reflns_theta_min         1.247
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.058
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    0.992
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             980.001
_exptl_crystal_size_max          0.492
_exptl_crystal_size_mid          0.283
_exptl_crystal_size_min          0.212
_refine_diff_density_max         0.98
_refine_diff_density_min         -0.83
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9949
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1012
_refine_ls_number_reflns         16876
_refine_ls_number_restraints     222
_refine_ls_R_factor_all          0.1665
_refine_ls_R_factor_gt           0.1130
_refine_ls_shift/su_max          0.0424106
_refine_ls_shift/su_mean         0.0040969
_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         0.4339
_refine_ls_wR_factor_gt          0.3528
_refine_ls_wR_factor_ref         0.4339
_reflns_limit_h_max              18
_reflns_limit_h_min              -18
_reflns_limit_k_max              19
_reflns_limit_k_min              -19
_reflns_limit_l_max              24
_reflns_limit_l_min              0
_reflns_number_gt                9019
_reflns_number_total             16876
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   4.31
_oxford_diffrn_Wilson_scale      51.12
_oxford_refine_ls_r_factor_ref   0.1665
_oxford_refine_ls_scale          0.1738(2)
_oxford_reflns_number_all        16876
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_cod_data_source_file            nchem.1668-s2.cif
_cod_data_source_block           11075
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C65 H65.00 N5'
_cod_database_code               1551390
_iucr_refine_instruction_details_constraints
;
BLOCK 
CONT SCALE 
CONT N    (    1 ,X'S,U'S)  UNTIL C    (   22 ) 
CONT C    (   23 ,X'S,U[ISO])  UNTIL C    (   25 ) 
CONT C    (   26 ,X'S,U'S)  UNTIL C    (   35 ) 
CONT C    (   36 ,X'S,U[ISO])  UNTIL C    (   38 ) 
CONT C    (   39 ,X'S,U'S)  UNTIL C    (   48 ) 
CONT C    (   49 ,X'S,U[ISO])  UNTIL C    (   51 ) 
CONT C    (   52 ,X'S,U'S)  UNTIL C    (  521 ) 
CONT C    (  523 ,X'S,U[ISO])  UNTIL C    (  525 ) 
CONT C    (  526 ,X'S,U'S)  UNTIL C    (  534 ) 
CONT C    (  536 ,X'S,U[ISO])  UNTIL C    (  538 ) 
CONT C    (  539 ,X'S,U'S)  UNTIL C    (  547 ) 
CONT C    (  549 ,X'S,U[ISO])  UNTIL C    (  551 ) 
CONT C    (  552 ,X'S,U'S)  UNTIL C    (  560 ) 
CONT C    (  562 ,X'S,U[ISO])  UNTIL C    (  564 ) 
CONT C    (  565 ,X'S,U'S) 
CONT C    (  623 ,X'S,U[ISO])  UNTIL C    (  625 ) 
SUMFIX PART(1001,OCC) AND PART(1002,OCC) 
SUMFIX PART(1003,OCC) AND PART(1004,OCC) AND PART(1011,OCC) 
SUMFIX PART(1005,OCC) AND PART(1006,OCC) 
SUMFIX PART(1007,OCC) AND PART(1008,OCC) 
SUMFIX PART(1009,OCC) AND PART(1010,OCC) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) H   ( 102,X'S) H   ( 103,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) H   ( 112,X'S) H   ( 113,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) H   ( 122,X'S) H   ( 123,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) H   ( 232,X'S) H   ( 233,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) H   ( 242,X'S) H   ( 243,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) H   ( 252,X'S) H   ( 253,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) 
RIDE C   (  34,X'S) H   ( 341,X'S) 
RIDE C   (  36,X'S) H   ( 361,X'S) H   ( 362,X'S) H   ( 363,X'S) 
RIDE C   (  37,X'S) H   ( 371,X'S) H   ( 372,X'S) H   ( 373,X'S) 
RIDE C   (  38,X'S) H   ( 381,X'S) H   ( 382,X'S) H   ( 383,X'S) 
RIDE C   (  39,X'S) H   ( 391,X'S) 
RIDE C   (  43,X'S) H   ( 431,X'S) 
RIDE C   (  45,X'S) H   ( 451,X'S) 
RIDE C   (  47,X'S) H   ( 471,X'S) 
RIDE C   (  49,X'S) H   ( 491,X'S) H   ( 492,X'S) H   ( 493,X'S) 
RIDE C   (  50,X'S) H   ( 501,X'S) H   ( 502,X'S) H   ( 503,X'S) 
RIDE C   (  51,X'S) H   ( 511,X'S) H   ( 512,X'S) H   ( 513,X'S) 
RIDE C   (  52,X'S) H   ( 521,X'S) 
RIDE C   (  56,X'S) H   ( 561,X'S) 
RIDE C   (  58,X'S) H   ( 581,X'S) 
RIDE C   (  60,X'S) H   ( 601,X'S) 
RIDE C   (  62,X'S) H   ( 621,X'S) H   ( 622,X'S) H   ( 623,X'S) 
RIDE C   (  63,X'S) H   ( 631,X'S) H   ( 632,X'S) H   ( 633,X'S) 
RIDE C   (  64,X'S) H   ( 641,X'S) H   ( 642,X'S) H   ( 643,X'S) 
RIDE C   (  65,X'S) H   ( 651,X'S) 
RIDE C   ( 504,X'S) H   (5041,X'S) 
RIDE C   ( 506,X'S) H   (5061,X'S) 
RIDE C   ( 508,X'S) H   (5081,X'S) 
RIDE C   ( 513,X'S) H   (5131,X'S) 
RIDE C   ( 517,X'S) H   (5171,X'S) 
RIDE C   ( 519,X'S) H   (5191,X'S) 
RIDE C   ( 521,X'S) H   (5211,X'S) 
RIDE C   ( 523,X'S) H   (5231,X'S) H   (5232,X'S) H   (5233,X'S) 
RIDE C   ( 524,X'S) H   (5241,X'S) H   (5242,X'S) H   (5243,X'S) 
RIDE C   ( 525,X'S) H   (5251,X'S) H   (5252,X'S) H   (5253,X'S) 
RIDE C   ( 526,X'S) H   (5261,X'S) 
RIDE C   ( 530,X'S) H   (5301,X'S) 
RIDE C   ( 532,X'S) H   (5321,X'S) 
RIDE C   ( 534,X'S) H   (5341,X'S) 
RIDE C   ( 536,X'S) H   (5361,X'S) H   (5362,X'S) H   (5363,X'S) 
RIDE C   ( 537,X'S) H   (5371,X'S) H   (5372,X'S) H   (5373,X'S) 
RIDE C   ( 538,X'S) H   (5381,X'S) H   (5382,X'S) H   (5383,X'S) 
RIDE C   ( 539,X'S) H   (5391,X'S) 
RIDE C   ( 543,X'S) H   (5431,X'S) 
RIDE C   ( 545,X'S) H   (5451,X'S) 
RIDE C   ( 547,X'S) H   (5471,X'S) 
RIDE C   ( 549,X'S) H   (5491,X'S) H   (5492,X'S) H   (5493,X'S) 
RIDE C   ( 550,X'S) H   (5501,X'S) H   (5502,X'S) H   (5503,X'S) 
RIDE C   ( 551,X'S) H   (5511,X'S) H   (5512,X'S) H   (5513,X'S) 
RIDE C   ( 552,X'S) H   (5521,X'S) 
RIDE C   ( 556,X'S) H   (5561,X'S) 
RIDE C   ( 558,X'S) H   (5581,X'S) 
RIDE C   ( 560,X'S) H   (5601,X'S) 
RIDE C   ( 562,X'S) H   (5621,X'S) H   (5622,X'S) H   (5623,X'S) 
RIDE C   ( 563,X'S) H   (5631,X'S) H   (5632,X'S) H   (5633,X'S) 
RIDE C   ( 564,X'S) H   (5641,X'S) H   (5642,X'S) H   (5643,X'S) 
RIDE C   ( 565,X'S) H   (5651,X'S) 
RIDE C   ( 623,X'S) H   (6231,X'S) H   (6232,X'S) H   (6233,X'S) 
RIDE C   ( 624,X'S) H   (6241,X'S) H   (6242,X'S) H   (6243,X'S) 
RIDE C   ( 625,X'S) H   (6251,X'S) H   (6252,X'S) H   (6253,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) 
SAME 0.01 0.1 
CONT C(20) C(22) C(23) C(24) C(25) AND 
CONT C(20) C(22) C(25) C(24) C(23) AND 
CONT C(20) C(22) C(523) C(524) C(525) AND 
CONT C(20) C(22) C(525) C(524) C(523) AND 
CONT C(20) C(22) C(623) C(624) C(625) AND 
CONT C(20) C(22) C(625) C(624) C(623) AND 
CONT C(33) C(35) C(36) C(37) C(38) AND 
CONT C(33) C(35) C(38) C(37) C(36) AND 
CONT C(33) C(35) C(536) C(537) C(538) AND 
CONT C(33) C(35) C(538) C(537) C(536) AND 
CONT C(46) C(48) C(49) C(50) C(51) AND 
CONT C(46) C(48) C(51) C(50) C(49) AND 
CONT C(46) C(48) C(549) C(550) C(551) AND 
CONT C(46) C(48) C(551) C(550) C(549) AND 
CONT C(59) C(61) C(62) C(63) C(64) AND 
CONT C(59) C(61) C(64) C(63) C(62) AND 
CONT C(59) C(61) C(562) C(563) C(564) AND 
CONT C(59) C(61) C(564) C(563) C(562) 
U(IJ)'S  0.0, 0.007000 = N(505) TO C(53) 
U(IJ)'S  0.0, 0.007000 = C(56) TO C(556) 
U(IJ)'S  0.0, 0.007000 = N(501) TO C(1) 
U(IJ)'S  0.0, 0.007000 = C(28) TO C(528) 
U(IJ)'S  0.0, 0.007000 = C(2) TO C(502) 
U(IJ)'S  0.0, 0.007000 = C(543) TO C(544) 
U(IJ)'S  0.0, 0.007000 = C(4) TO C(504) 
END                                                                             
;