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_1520623
_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_absolute_configuration ad
_chemical_formula_moiety
'C12 H22 O6, 0.5(C16 H36 N), 0.5(C4 H8 O3), 0.5(F)'
_chemical_formula_sum            'C22 H44 F0.5 N0.5 O7'
_chemical_formula_weight         437.09
_chemical_melting_point          362
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2014-12-19
_audit_creation_method           CRYSTALS_ver_14.43
_audit_update_record
;
2015-05-19 deposited with the CCDC.
2015-06-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.2457(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   25.1923(1)
_cell_length_b                   9.6565(1)
_cell_length_c                   10.6715(1)
_cell_measurement_reflns_used    43761
_cell_measurement_temperature    150
_cell_measurement_theta_max      76
_cell_measurement_theta_min      4
_cell_volume                     2594.06(4)
_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    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.020
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            49863
_diffrn_reflns_theta_full        76.028
_diffrn_reflns_theta_max         76.028
_diffrn_reflns_theta_min         3.511
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.689
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.119
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.20
_refine_ls_abs_structure_details 'Flack (1983), 2510 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.02(10)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         5353
_refine_ls_number_restraints     623
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0326
_refine_ls_shift/su_max          0.0003897
_refine_ls_shift/su_mean         0.0000321
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.06P)^2^ + 0.76P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0889
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0889
_reflns_limit_h_max              31
_reflns_limit_h_min              -31
_reflns_limit_k_max              12
_reflns_limit_k_min              -12
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                5330
_reflns_number_total             5371
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.21
_oxford_diffrn_Wilson_scale      0.07
_oxford_refine_ls_r_factor_ref   0.0327
_oxford_refine_ls_scale          5.14(7)
_oxford_reflns_number_all        5353
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 003lp14
_iucr_refine_instructions_details_constraints
;
BLOCK SCALE X'S U'S 
CONT ENANTIO 
EQUIV PART(1001,OCC) PART(1002,OCC) 
WEIGHT -1 PART(1002,OCC) 
REM EQUIV PART(-2002,OCC) PART(-2003,OCC) 
REM WEIGHT -1 PART(-2003,OCC) 
RIDE  C(25,U'S) C(125,U'S) 
RIDE  O(26,U'S) O(126,U'S) 
RIDE O   (   1,X'S) H   (  11,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 132,X'S) H   ( 131,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) H   ( 173,X'S) H   ( 172,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) H   ( 182,X'S) H   ( 183,X'S) 
RIDE O   (   2,X'S) H   (  21,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) H   ( 232,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) H   ( 273,X'S) H   ( 272,X'S) 
RIDE C   (  28,X'S) H   (  22,X'S) H   ( 282,X'S) H   ( 283,X'S) 
RIDE C   ( 127,X'S) H   (1271,X'S) H   (1273,X'S) H   (1272,X'S) 
RIDE C   ( 128,X'S) H   (1281,X'S) H   (1282,X'S) H   (1283,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) H   ( 322,X'S) 
RIDE C   (  33,X'S) H   ( 332,X'S) H   ( 331,X'S) 
RIDE C   (  34,X'S) H   ( 342,X'S) H   ( 341,X'S) 
RIDE C   (  35,X'S) H   ( 352,X'S) H   ( 353,X'S) H   ( 351,X'S) 
RIDE C   (  36,X'S) H   ( 362,X'S) H   ( 361,X'S) 
RIDE C   (  37,X'S) H   ( 372,X'S) H   ( 371,X'S) 
RIDE C   (  38,X'S) H   ( 381,X'S) H   ( 382,X'S) 
RIDE C   (  39,X'S) H   ( 391,X'S) H   ( 393,X'S) H   ( 392,X'S) 
RIDE C   (  43,X'S) H   ( 431,X'S) H   ( 432,X'S) H   ( 433,X'S) 
RIDE C   (  45,X'S) H   ( 452,X'S) H   ( 451,X'S) 
RIDE C   (  46,X'S) H   ( 462,X'S) H   ( 461,X'S) H   ( 463,X'S) 
REM RIDE C   (  45,X'S) H   ( 453,X'S) H   ( 452,X'S) H   ( 451,X'S) 
REM RIDE C   ( 146,X'S) H   (1461,X'S) H   (1462,X'S) H   (1463,X'S) 
END                                                                             
;
_iucr_refine_instructions_details_restraints
;
REM SAME  O(44)  C(45)  C(46)  C(146)  AND 
REM CONT  O(44)  C(45)  C(146)  C(46) 
REM SIMU  0.01   O(44)  C(45)  C(46)  C(146)  AND 
REM CONT  O(44)  C(45)  C(146)  C(46) 
REM DELU  0.01   O(44)  C(45)  C(46)  C(146)  AND 
REM CONT  O(44)  C(45)  C(146)  C(46) 
DIST  0,0.01 = MEAN 
CONT  C(42) TO  C(43)  C(45) TO  C(46) 
VIBR .0, 0.00200 = O(41) TO C(42) 
VIBR .0, 0.00200 = C(42) TO O(44) 
VIBR .0, 0.00200 = C(42) TO C(43) 
VIBR .0, 0.00500 = O(44) TO O(41) 
VIBR .0, 0.00500 = C(43) TO O(41) 
VIBR .0, 0.00500 = C(43) TO O(44) 
U(IJ) .0, 0.08000 = O(41) TO C(42) 
U(IJ) .0, 0.04000 = C(42) TO O(44) 
U(IJ) .0, 0.08000 = C(42) TO C(43) 
U(IJ) .0, 0.08000 = C(46) TO C(45) 
SAME  O(24)  C(25)  O(26)  C(27)  C(28)  AND 
CONT  O(26)  C(25)  O(24)  C(28)  C(27)  AND 
CONT  O(24)  C(125)  O(126)  C(127)  C(128)  AND 
CONT  O(126)  C(125)  O(24)  C(128)  C(127) 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_cod_data_source_file            c5sc01812a2.cif
_cod_data_source_block           2f
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '362 K' was changed to '362' - the
value should be numeric and without a unit designator.

'_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.

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_H-M      'C 2 '
_cod_original_formula_sum        'C22 H44 F0.50 N0.50 O7'
_cod_database_code               1520623