Coordination diversity in hydrogen-bonded homoleptic fluoride–alcohol complexes modulates reactivity
Engle, Keary M.; Pfeifer, Lukas; Pidgeon, George W.; Giuffredi, Guy T.; Thompson, Amber L.; Paton, Robert S.; Brown, John M.; Gouverneur, Véronique; Chem. Sci. 6 (2015) 5293–; doi:10.1039/C5SC01812A

data_1520630
_publ_section_title
;
 Coordination diversity in hydrogen-bonded homoleptic fluoride--alcohol
 complexes modulates reactivity
;
_journal_issue                   9
_journal_name_full               'Chem. Sci.'
_journal_page_first              5293
_journal_paper_doi               10.1039/C5SC01812A
_journal_volume                  6
_journal_year                    2015
_chemical_formula_moiety         '2(C22 H22 O), C16 H36 N, F'
_chemical_formula_sum            'C60 H80 F N O2'
_chemical_formula_weight         866.30
_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     direct
_audit_creation_date             13-04-25
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2015-05-19 deposited with the CCDC.
2015-06-22 downloaded from the CCDC.
;
_cell_angle_alpha                78.8655(19)
_cell_angle_beta                 80.5422(17)
_cell_angle_gamma                69.645(2)
_cell_formula_units_Z            4
_cell_length_a                   13.4717(3)
_cell_length_b                   17.5643(4)
_cell_length_c                   24.8506(5)
_cell_measurement_reflns_used    46180
_cell_measurement_temperature    150
_cell_measurement_theta_max      77
_cell_measurement_theta_min      3
_cell_volume                     5379.0(2)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_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 0.997
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.033
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            110583
_diffrn_reflns_theta_full        74.851
_diffrn_reflns_theta_max         77.166
_diffrn_reflns_theta_min         3.038
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.500
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.070
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.33
_refine_diff_density_min         -0.21
_refine_ls_extinction_coef       111(12)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   0.9911
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1154
_refine_ls_number_reflns         22370
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0439
_refine_ls_shift/su_max          0.0008843
_refine_ls_shift/su_mean         0.0001389
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.06P)^2^ + 1.56P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1204
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1203
_reflns_limit_h_max              17
_reflns_limit_h_min              -16
_reflns_limit_k_max              22
_reflns_limit_k_min              -21
_reflns_limit_l_max              31
_reflns_limit_l_min              0
_reflns_number_gt                19453
_reflns_number_total             22463
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.11
_oxford_diffrn_Wilson_scale      0.08
_oxford_refine_ls_r_factor_ref   0.0502
_oxford_refine_ls_scale          3.56(2)
_oxford_reflns_number_all        22373
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 048gwp12
_cod_data_source_file            c5sc01812a2.cif
_cod_data_source_block           2m
_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.

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

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 1520618--1520631.cif.
;
_cod_original_sg_symbol_Hall     '-P 1 '
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C60 H80 F1 N1 O2'
_cod_database_code               1520630
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT EXTPARAM 
RIDE C   (  91,X'S) H   ( 912,X'S) H   ( 911,X'S) H   ( 913,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) H   ( 183,X'S) H   ( 182,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  21,X'S) H   ( 211,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   ( 253,X'S) H   ( 252,X'S) H   ( 251,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) H   ( 322,X'S) H   ( 323,X'S) 
RIDE C   (  43,X'S) H   ( 431,X'S) 
RIDE C   (  44,X'S) H   ( 441,X'S) 
RIDE C   (  46,X'S) H   ( 461,X'S) 
RIDE C   (  47,X'S) H   ( 471,X'S) 
RIDE C   (  48,X'S) H   ( 481,X'S) H   ( 482,X'S) H   ( 483,X'S) 
RIDE C   (  50,X'S) H   ( 501,X'S) 
RIDE C   (  51,X'S) H   ( 511,X'S) 
RIDE C   (  53,X'S) H   ( 531,X'S) 
RIDE C   (  54,X'S) H   ( 541,X'S) 
RIDE C   (  55,X'S) H   ( 552,X'S) H   ( 551,X'S) H   ( 553,X'S) 
RIDE C   (  57,X'S) H   ( 571,X'S) 
RIDE C   (  58,X'S) H   ( 581,X'S) 
RIDE C   (  60,X'S) H   ( 601,X'S) 
RIDE C   (  61,X'S) H   ( 611,X'S) 
RIDE C   (  62,X'S) H   ( 623,X'S) H   ( 622,X'S) H   ( 621,X'S) 
RIDE C   (  73,X'S) H   ( 731,X'S) 
RIDE C   (  74,X'S) H   ( 741,X'S) 
RIDE C   (  76,X'S) H   ( 761,X'S) 
RIDE C   (  77,X'S) H   ( 771,X'S) 
RIDE C   (  78,X'S) H   ( 781,X'S) H   ( 782,X'S) H   ( 783,X'S) 
RIDE C   (  80,X'S) H   ( 801,X'S) 
RIDE C   (  81,X'S) H   ( 811,X'S) 
RIDE C   (  83,X'S) H   ( 831,X'S) 
RIDE C   (  84,X'S) H   ( 841,X'S) 
RIDE C   (  85,X'S) H   ( 853,X'S) H   ( 852,X'S) H   ( 851,X'S) 
RIDE C   (  87,X'S) H   ( 871,X'S) 
RIDE C   (  88,X'S) H   ( 881,X'S) 
RIDE C   (  90,X'S) H   ( 901,X'S) 
RIDE C   ( 238,X'S) H   (2381,X'S) 
RIDE C   ( 103,X'S) H   (1031,X'S) 
RIDE C   ( 104,X'S) H   (1041,X'S) 
RIDE C   ( 106,X'S) H   (1061,X'S) 
RIDE C   ( 107,X'S) H   (1071,X'S) 
RIDE C   ( 108,X'S) H   (1081,X'S) H   (1083,X'S) H   (1082,X'S) 
RIDE C   ( 110,X'S) H   (1101,X'S) 
RIDE C   ( 111,X'S) H   (1111,X'S) 
RIDE C   ( 113,X'S) H   (1131,X'S) 
RIDE C   ( 114,X'S) H   (1141,X'S) 
RIDE C   ( 115,X'S) H   (1151,X'S) H   (1152,X'S) H   (1153,X'S) 
RIDE C   ( 117,X'S) H   (1171,X'S) 
RIDE C   ( 118,X'S) H   (1181,X'S) 
RIDE C   ( 120,X'S) H   (1201,X'S) 
RIDE C   ( 121,X'S) H   (1211,X'S) 
RIDE C   ( 122,X'S) H   (1223,X'S) H   (1221,X'S) H   (1222,X'S) 
RIDE O   (   1,X'S) H   (  11,X'S) 
RIDE O   (   2,X'S) H   (  21,X'S) 
RIDE O   (   3,X'S) H   (  31,X'S) 
RIDE O   (   4,X'S) H   (  41,X'S) 
RIDE C   ( 202,X'S) H   (2021,X'S) H   (2022,X'S) 
RIDE C   ( 203,X'S) H   (2031,X'S) H   (2032,X'S) 
RIDE C   ( 204,X'S) H   (2041,X'S) H   (2042,X'S) 
RIDE C   ( 205,X'S) H   (2051,X'S) H   (2052,X'S) H   (2053,X'S) 
RIDE C   ( 206,X'S) H   (2061,X'S) H   (2062,X'S) 
RIDE C   ( 207,X'S) H   (2071,X'S) H   (2072,X'S) 
RIDE C   ( 208,X'S) H   (2081,X'S) H   (2082,X'S) 
RIDE C   ( 209,X'S) H   (2091,X'S) H   (2092,X'S) H   (2093,X'S) 
RIDE C   ( 210,X'S) H   (2101,X'S) H   (2102,X'S) 
RIDE C   ( 211,X'S) H   (2111,X'S) H   (2112,X'S) 
RIDE C   ( 212,X'S) H   (2121,X'S) H   (2122,X'S) 
RIDE C   ( 213,X'S) H   (2133,X'S) H   (2132,X'S) H   (2131,X'S) 
RIDE C   ( 214,X'S) H   (2141,X'S) H   (2142,X'S) 
RIDE C   ( 215,X'S) H   (2151,X'S) H   (2152,X'S) 
RIDE C   ( 216,X'S) H   (2161,X'S) H   (2162,X'S) 
RIDE C   ( 217,X'S) H   (2173,X'S) H   (2172,X'S) H   (2171,X'S) 
RIDE C   ( 222,X'S) H   (2221,X'S) H   (2222,X'S) 
RIDE C   ( 223,X'S) H   (2231,X'S) H   (2232,X'S) 
RIDE C   ( 224,X'S) H   (2241,X'S) H   (2242,X'S) 
RIDE C   ( 225,X'S) H   (2253,X'S) H   (2252,X'S) H   (2251,X'S) 
RIDE C   ( 226,X'S) H   (2261,X'S) H   (2262,X'S) 
RIDE C   ( 227,X'S) H   (2271,X'S) H   (2272,X'S) 
RIDE C   ( 228,X'S) H   (2281,X'S) H   (2282,X'S) 
RIDE C   ( 229,X'S) H   (2291,X'S) H   (2292,X'S) H   (2293,X'S) 
RIDE C   ( 230,X'S) H   (2301,X'S) H   (2302,X'S) 
RIDE C   ( 231,X'S) H   (2311,X'S) H   (2312,X'S) 
RIDE C   ( 232,X'S) H   (2321,X'S) H   (2322,X'S) 
RIDE C   ( 233,X'S) H   (2331,X'S) H   (2332,X'S) H   (2333,X'S) 
RIDE C   ( 234,X'S) H   (2341,X'S) H   (2342,X'S) 
RIDE C   ( 235,X'S) H   (2351,X'S) H   (2352,X'S) 
RIDE C   ( 236,X'S) H   (2361,X'S) H   (2362,X'S) 
RIDE C   ( 237,X'S) H   (2373,X'S) H   (2372,X'S) H   (2371,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) 
END                                                                             
;