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_1520627
_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         '3(C19 H14 O), C16 H36 N, F'
_chemical_formula_sum            'C73 H78 F N O3'
_chemical_formula_weight         1036.43
_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             12-11-30
_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                91.2454(7)
_cell_angle_beta                 94.4191(7)
_cell_angle_gamma                103.9009(8)
_cell_formula_units_Z            4
_cell_length_a                   14.5683(1)
_cell_length_b                   19.9837(2)
_cell_length_c                   20.7534(2)
_cell_measurement_reflns_used    141894
_cell_measurement_temperature    150
_cell_measurement_theta_max      76
_cell_measurement_theta_min      3
_cell_volume                     5842.46(9)
_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 0.997
_diffrn_measured_fraction_theta_max 0.992
_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  0.026
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            227665
_diffrn_reflns_theta_full        75.122
_diffrn_reflns_theta_max         76.656
_diffrn_reflns_theta_min         3.060
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.561
_exptl_absorpt_correction_T_max  0.89
_exptl_absorpt_correction_T_min  0.47
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2224
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.52
_refine_diff_density_min         -0.30
_refine_ls_extinction_coef       170(9)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   0.9862
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1406
_refine_ls_number_reflns         20878
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.0005741
_refine_ls_shift/su_mean         0.0000404
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 2.94P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0976
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.0976
_reflns_limit_h_max              18
_reflns_limit_h_min              -18
_reflns_limit_k_max              25
_reflns_limit_k_min              -25
_reflns_limit_l_max              26
_reflns_limit_l_min              0
_reflns_number_gt                19535
_reflns_number_total             24424
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.72
_oxford_diffrn_Wilson_scale      0.11
_oxford_refine_ls_r_factor_ref   0.0429
_oxford_refine_ls_scale          3.079(15)
_oxford_reflns_number_all        20878
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 004gwp12
_cod_data_source_file            c5sc01812a2.cif
_cod_data_source_block           2j
_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 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 1520618--1520631.cif.
;
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C73 H78 F1 N1 O3'
_cod_database_code               1520627
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT EXTPARAM 
RIDE O   (  11,X'S) H   ( 111,X'S) 
RIDE O   (  12,X'S) H   ( 121,X'S) 
RIDE O   (  13,X'S) H   ( 131,X'S) 
RIDE O   (  14,X'S) H   ( 141,X'S) 
RIDE O   (  15,X'S) H   ( 151,X'S) 
RIDE O   (  16,X'S) H   ( 161,X'S) 
RIDE C   ( 103,X'S) H   (1031,X'S) 
RIDE C   ( 104,X'S) H   (1041,X'S) 
RIDE C   ( 105,X'S) H   (1051,X'S) 
RIDE C   ( 106,X'S) H   (1061,X'S) 
RIDE C   ( 110,X'S) H   (1101,X'S) 
RIDE C   ( 111,X'S) H   (1111,X'S) 
RIDE C   ( 112,X'S) H   (1121,X'S) 
RIDE C   ( 113,X'S) H   (1131,X'S) 
RIDE C   ( 115,X'S) H   (1151,X'S) 
RIDE C   ( 116,X'S) H   (1161,X'S) 
RIDE C   ( 117,X'S) H   (1171,X'S) 
RIDE C   ( 118,X'S) H   (1181,X'S) 
RIDE C   ( 119,X'S) H   (1191,X'S) 
RIDE C   ( 122,X'S) H   (1221,X'S) 
RIDE C   ( 123,X'S) H   (1231,X'S) 
RIDE C   ( 124,X'S) H   (1241,X'S) 
RIDE C   ( 125,X'S) H   (1251,X'S) 
RIDE C   ( 129,X'S) H   (1291,X'S) 
RIDE C   ( 130,X'S) H   (1301,X'S) 
RIDE C   ( 131,X'S) H   (1311,X'S) 
RIDE C   ( 132,X'S) H   (1321,X'S) 
RIDE C   ( 134,X'S) H   (1341,X'S) 
RIDE C   ( 135,X'S) H   (1351,X'S) 
RIDE C   ( 136,X'S) H   (1361,X'S) 
RIDE C   ( 137,X'S) H   (1371,X'S) 
RIDE C   ( 138,X'S) H   (1381,X'S) 
RIDE C   ( 141,X'S) H   (1411,X'S) 
RIDE C   ( 142,X'S) H   (1421,X'S) 
RIDE C   ( 143,X'S) H   (1431,X'S) 
RIDE C   ( 144,X'S) H   (1441,X'S) 
RIDE C   ( 148,X'S) H   (1481,X'S) 
RIDE C   ( 149,X'S) H   (1491,X'S) 
RIDE C   ( 150,X'S) H   (1501,X'S) 
RIDE C   ( 151,X'S) H   (1511,X'S) 
RIDE C   ( 153,X'S) H   (1531,X'S) 
RIDE C   ( 154,X'S) H   (1541,X'S) 
RIDE C   ( 155,X'S) H   (1551,X'S) 
RIDE C   ( 156,X'S) H   (1561,X'S) 
RIDE C   ( 157,X'S) H   (1571,X'S) 
RIDE C   ( 160,X'S) H   (1601,X'S) 
RIDE C   ( 161,X'S) H   (1611,X'S) 
RIDE C   ( 162,X'S) H   (1621,X'S) 
RIDE C   ( 163,X'S) H   (1631,X'S) 
RIDE C   ( 167,X'S) H   (1671,X'S) 
RIDE C   ( 168,X'S) H   (1681,X'S) 
RIDE C   ( 169,X'S) H   (1691,X'S) 
RIDE C   ( 170,X'S) H   (1701,X'S) 
RIDE C   ( 172,X'S) H   (1721,X'S) 
RIDE C   ( 173,X'S) H   (1731,X'S) 
RIDE C   ( 174,X'S) H   (1741,X'S) 
RIDE C   ( 175,X'S) H   (1751,X'S) 
RIDE C   ( 176,X'S) H   (1761,X'S) 
RIDE C   ( 179,X'S) H   (1791,X'S) 
RIDE C   ( 180,X'S) H   (1801,X'S) 
RIDE C   ( 181,X'S) H   (1811,X'S) 
RIDE C   ( 182,X'S) H   (1821,X'S) 
RIDE C   ( 186,X'S) H   (1861,X'S) 
RIDE C   ( 187,X'S) H   (1871,X'S) 
RIDE C   ( 188,X'S) H   (1881,X'S) 
RIDE C   ( 189,X'S) H   (1891,X'S) 
RIDE C   ( 191,X'S) H   (1911,X'S) 
RIDE C   ( 192,X'S) H   (1921,X'S) 
RIDE C   ( 193,X'S) H   (1931,X'S) 
RIDE C   ( 194,X'S) H   (1941,X'S) 
RIDE C   ( 195,X'S) H   (1951,X'S) 
RIDE C   ( 198,X'S) H   (1981,X'S) 
RIDE C   ( 199,X'S) H   (1991,X'S) 
RIDE C   ( 200,X'S) H   (2001,X'S) 
RIDE C   ( 201,X'S) H   (2011,X'S) 
RIDE C   ( 205,X'S) H   (2051,X'S) 
RIDE C   ( 206,X'S) H   (2061,X'S) 
RIDE C   ( 207,X'S) H   (2071,X'S) 
RIDE C   ( 208,X'S) H   (2081,X'S) 
RIDE C   ( 210,X'S) H   (2101,X'S) 
RIDE C   ( 211,X'S) H   (2111,X'S) 
RIDE C   ( 212,X'S) H   (2121,X'S) 
RIDE C   ( 213,X'S) H   (2131,X'S) 
RIDE C   ( 214,X'S) H   (2141,X'S) 
RIDE C   ( 502,X'S) H   (5021,X'S) H   (5022,X'S) 
RIDE C   ( 503,X'S) H   (5031,X'S) H   (5032,X'S) 
RIDE C   ( 504,X'S) H   (5041,X'S) H   (5042,X'S) 
RIDE C   ( 505,X'S) H   (5052,X'S) H   (5053,X'S) H   (5051,X'S) 
RIDE C   ( 506,X'S) H   (5061,X'S) H   (5062,X'S) 
RIDE C   ( 507,X'S) H   (5071,X'S) H   (5072,X'S) 
RIDE C   ( 508,X'S) H   (5081,X'S) H   (5082,X'S) 
RIDE C   ( 509,X'S) H   (5093,X'S) H   (5092,X'S) H   (5091,X'S) 
RIDE C   ( 510,X'S) H   (5101,X'S) H   (5102,X'S) 
RIDE C   ( 511,X'S) H   (5111,X'S) H   (5112,X'S) 
RIDE C   ( 512,X'S) H   (5121,X'S) H   (5122,X'S) 
RIDE C   ( 513,X'S) H   (5133,X'S) H   (5131,X'S) H   (5132,X'S) 
RIDE C   ( 514,X'S) H   (5141,X'S) H   (5142,X'S) 
RIDE C   ( 515,X'S) H   (5151,X'S) H   (5152,X'S) 
RIDE C   ( 516,X'S) H   (5161,X'S) H   (5162,X'S) 
RIDE C   ( 517,X'S) H   (5172,X'S) H   (5171,X'S) H   (5173,X'S) 
RIDE C   ( 522,X'S) H   (5221,X'S) H   (5222,X'S) 
RIDE C   ( 523,X'S) H   (5231,X'S) H   (5232,X'S) 
RIDE C   ( 524,X'S) H   (5241,X'S) H   (5242,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) H   (5262,X'S) 
RIDE C   ( 527,X'S) H   (5271,X'S) H   (5272,X'S) 
RIDE C   ( 528,X'S) H   (5281,X'S) H   (5282,X'S) 
RIDE C   ( 529,X'S) H   (5291,X'S) H   (5292,X'S) H   (5293,X'S) 
RIDE C   ( 530,X'S) H   (5301,X'S) H   (5302,X'S) 
RIDE C   ( 531,X'S) H   (5311,X'S) H   (5312,X'S) 
RIDE C   ( 532,X'S) H   (5321,X'S) H   (5322,X'S) 
RIDE C   ( 533,X'S) H   (5331,X'S) H   (5332,X'S) H   (5333,X'S) 
RIDE C   ( 534,X'S) H   (5342,X'S) H   (5341,X'S) 
RIDE C   ( 535,X'S) H   (5352,X'S) H   (5351,X'S) 
RIDE C   ( 536,X'S) H   (5361,X'S) H   (5362,X'S) 
RIDE C   ( 537,X'S) H   (5371,X'S) H   (5372,X'S) H   (5373,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                                                                             
;