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_1520629
_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(C19 H16 O), C16 H36 N, F'
_chemical_formula_sum            'C54 H68 F N O2'
_chemical_formula_weight         782.14
_chemical_melting_point          ?
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                90
_cell_angle_beta                 98.4318(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2887(1)
_cell_length_b                   17.6025(1)
_cell_length_c                   24.9660(2)
_cell_measurement_reflns_used    49297
_cell_measurement_temperature    150
_cell_measurement_theta_max      77
_cell_measurement_theta_min      3
_cell_volume                     4907.35(7)
_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 0.997
_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  0.035
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            117478
_diffrn_reflns_theta_full        76.917
_diffrn_reflns_theta_max         76.917
_diffrn_reflns_theta_min         3.083
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.504
_exptl_absorpt_correction_T_max  0.90
_exptl_absorpt_correction_T_min  0.20
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.059
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1696.000
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_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         0.69
_refine_diff_density_min         -0.60
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9822
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     836
_refine_ls_number_reflns         10304
_refine_ls_number_restraints     1269
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0553
_refine_ls_shift/su_max          0.0008927
_refine_ls_shift/su_mean         0.0000764
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.07P)^2^ + 1.96P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1454
_refine_ls_wR_factor_gt          0.1394
_refine_ls_wR_factor_ref         0.1454
_reflns_limit_h_max              14
_reflns_limit_h_min              -14
_reflns_limit_k_max              22
_reflns_limit_k_min              0
_reflns_limit_l_max              31
_reflns_limit_l_min              0
_reflns_number_gt                8934
_reflns_number_total             10345
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   4.03
_oxford_diffrn_Wilson_scale      0.10
_oxford_refine_ls_r_factor_ref   0.0614
_oxford_refine_ls_scale          3.35(4)
_oxford_reflns_number_all        10304
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 010gwp12
_cod_data_source_file            c5sc01812a2.cif
_cod_data_source_block           2l
_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_H-M      'P 21/n '
_cod_original_formula_sum        'C54 H68 F1 N1 O2'
_cod_database_code               1520629
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S U'S 
EQUIV PART(1001,OCC) PART(1002,OCC) 
WEIGHT -1 PART(1002,OCC) 
EQUIV PART(2001,OCC) PART(2002,OCC) 
WEIGHT -1 PART(2002,OCC) 
EQUIV PART(3001,OCC) PART(3002,OCC) 
WEIGHT -1 PART(3002,OCC) 
EQUIV PART(4001,OCC) PART(4002,OCC) 
WEIGHT -1 PART(4002,OCC) 
EQUIV PART(5001,OCC) PART(5002,OCC) 
WEIGHT -1 PART(5002,OCC) 
EQUIV PART(6001,OCC) PART(6002,OCC) 
WEIGHT -1 PART(6002,OCC) 
EQUIV PART(7001,OCC) PART(7002,OCC) 
WEIGHT -1 PART(7002,OCC) 
RIDE O   (   1,X'S) H   (  11,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   ( 107,X'S) H   (1071,X'S) 
RIDE C   ( 109,X'S) H   (1091,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 O   (   2,X'S) H   (  21,X'S) 
RIDE C   ( 203,X'S) H   (2031,X'S) 
RIDE C   ( 204,X'S) H   (2041,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   ( 209,X'S) H   (2091,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   ( 215,X'S) H   (2151,X'S) 
RIDE C   ( 216,X'S) H   (2161,X'S) 
RIDE C   ( 217,X'S) H   (2171,X'S) 
RIDE C   ( 218,X'S) H   (2181,X'S) 
RIDE C   ( 219,X'S) H   (2191,X'S) 
RIDE C   ( 309,X'S) H   (3091,X'S) 
RIDE C   ( 310,X'S) H   (3101,X'S) 
RIDE C   ( 311,X'S) H   (3111,X'S) 
RIDE C   ( 312,X'S) H   (3121,X'S) 
RIDE C   ( 313,X'S) H   (3131,X'S) 
RIDE C   ( 315,X'S) H   (3151,X'S) 
RIDE C   ( 316,X'S) H   (3161,X'S) 
RIDE C   ( 317,X'S) H   (3171,X'S) 
RIDE C   ( 318,X'S) H   (3181,X'S) 
RIDE C   ( 319,X'S) H   (3191,X'S) 
RIDE C   ( 409,X'S) H   (4091,X'S) 
RIDE C   ( 410,X'S) H   (4101,X'S) 
RIDE C   ( 411,X'S) H   (4111,X'S) 
RIDE C   ( 412,X'S) H   (4121,X'S) 
RIDE C   ( 413,X'S) H   (4131,X'S) 
RIDE C   ( 415,X'S) H   (4151,X'S) 
RIDE C   ( 416,X'S) H   (4161,X'S) 
RIDE C   ( 417,X'S) H   (4171,X'S) 
RIDE C   ( 418,X'S) H   (4181,X'S) 
RIDE C   ( 419,X'S) H   (4191,X'S) 
RIDE C   ( 502,X'S) H   (5022,X'S) H   (5021,X'S) 
RIDE C   ( 503,X'S) H   (5031,X'S) H   (5032,X'S) 
RIDE C   ( 504,X'S) H   (5042,X'S) H   (5041,X'S) 
RIDE C   ( 505,X'S) H   (5053,X'S) H   (5052,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   (5082,X'S) H   (5081,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   (5112,X'S) H   (5111,X'S) 
RIDE C   ( 512,X'S) H   (5122,X'S) H   (5121,X'S) 
RIDE C   ( 513,X'S) H   (5131,X'S) H   (5132,X'S) H   (5133,X'S) 
RIDE C   ( 514,X'S) H   (5142,X'S) H   (5141,X'S) 
RIDE C   ( 515,X'S) H   (5151,X'S) H   (5152,X'S) 
CONT H   (5153,X'S) H   (5154,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   ( 606,X'S) H   (6062,X'S) H   (6061,X'S) 
RIDE C   ( 607,X'S) H   (6071,X'S) H   (6072,X'S) 
RIDE C   ( 608,X'S) H   (6082,X'S) H   (6081,X'S) 
RIDE C   ( 609,X'S) H   (6091,X'S) H   (6092,X'S) H   (6093,X'S) 
RIDE C   ( 610,X'S) H   (6102,X'S) H   (6101,X'S) 
RIDE C   ( 611,X'S) H   (6112,X'S) H   (6111,X'S) 
RIDE C   ( 612,X'S) H   (6121,X'S) H   (6122,X'S) 
RIDE C   ( 613,X'S) H   (6133,X'S) H   (6132,X'S) H   (6131,X'S) 
RIDE C   ( 617,X'S) H   (6172,X'S) H   (6171,X'S) 
RIDE C   ( 618,X'S) H   (6181,X'S) H   (6182,X'S) H   (6183,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
REM 
REM ALCOHOL 
REM 
SAME  C(101)  C(108)  C(109)  C(110)  C(111)  C(112)  C(113)  AND 
CONT  C(101)  C(108)  C(113)  C(112)  C(111)  C(110)  C(109)  AND 
CONT  C(101)  C(114)  C(115)  C(116)  C(117)  C(118)  C(119)  AND 
CONT  C(101)  C(114)  C(119)  C(118)  C(117)  C(116)  C(115)  AND 
CONT  C(201)  C(208)  C(209)  C(210)  C(211)  C(212)  C(213)  AND 
CONT  C(201)  C(208)  C(213)  C(212)  C(211)  C(210)  C(209)  AND 
CONT  C(201)  C(214)  C(215)  C(216)  C(217)  C(218)  C(219)  AND 
CONT  C(201)  C(214)  C(219)  C(218)  C(217)  C(216)  C(215)  AND 
CONT  C(101)  C(308)  C(309)  C(310)  C(311)  C(312)  C(313)  AND 
CONT  C(101)  C(308)  C(313)  C(312)  C(311)  C(310)  C(309)  AND 
CONT  C(101)  C(314)  C(315)  C(316)  C(317)  C(318)  C(319)  AND 
CONT  C(101)  C(314)  C(319)  C(318)  C(317)  C(316)  C(315)  AND 
CONT  C(201)  C(408)  C(409)  C(410)  C(411)  C(412)  C(413)  AND 
CONT  C(201)  C(408)  C(413)  C(412)  C(411)  C(410)  C(409)  AND 
CONT  C(201)  C(414)  C(415)  C(416)  C(417)  C(418)  C(419)  AND 
CONT  C(201)  C(414)  C(419)  C(418)  C(417)  C(416)  C(415) 
SIMU  0.01    C(101)  C(108)  C(109)  C(110)  C(111)  C(112)  C(113)  AND 
CONT  C(101)  C(108)  C(113)  C(112)  C(111)  C(110)  C(109)  AND 
CONT  C(101)  C(114)  C(115)  C(116)  C(117)  C(118)  C(119)  AND 
CONT  C(101)  C(114)  C(119)  C(118)  C(117)  C(116)  C(115)  AND 
CONT  C(201)  C(208)  C(209)  C(210)  C(211)  C(212)  C(213)  AND 
CONT  C(201)  C(208)  C(213)  C(212)  C(211)  C(210)  C(209)  AND 
CONT  C(201)  C(214)  C(215)  C(216)  C(217)  C(218)  C(219)  AND 
CONT  C(201)  C(214)  C(219)  C(218)  C(217)  C(216)  C(215)  AND 
CONT  C(101)  C(308)  C(309)  C(310)  C(311)  C(312)  C(313)  AND 
CONT  C(101)  C(308)  C(313)  C(312)  C(311)  C(310)  C(309)  AND 
CONT  C(101)  C(314)  C(315)  C(316)  C(317)  C(318)  C(319)  AND 
CONT  C(101)  C(314)  C(319)  C(318)  C(317)  C(316)  C(315)  AND 
CONT  C(201)  C(408)  C(409)  C(410)  C(411)  C(412)  C(413)  AND 
CONT  C(201)  C(408)  C(413)  C(412)  C(411)  C(410)  C(409)  AND 
CONT  C(201)  C(414)  C(415)  C(416)  C(417)  C(418)  C(419)  AND 
CONT  C(201)  C(414)  C(419)  C(418)  C(417)  C(416)  C(415) 
DELU  0.01    C(101)  C(108)  C(109)  C(110)  C(111)  C(112)  C(113)  AND 
CONT  C(101)  C(108)  C(113)  C(112)  C(111)  C(110)  C(109)  AND 
CONT  C(101)  C(114)  C(115)  C(116)  C(117)  C(118)  C(119)  AND 
CONT  C(101)  C(114)  C(119)  C(118)  C(117)  C(116)  C(115)  AND 
CONT  C(201)  C(208)  C(209)  C(210)  C(211)  C(212)  C(213)  AND 
CONT  C(201)  C(208)  C(213)  C(212)  C(211)  C(210)  C(209)  AND 
CONT  C(201)  C(214)  C(215)  C(216)  C(217)  C(218)  C(219)  AND 
CONT  C(201)  C(214)  C(219)  C(218)  C(217)  C(216)  C(215)  AND 
CONT  C(101)  C(308)  C(309)  C(310)  C(311)  C(312)  C(313)  AND 
CONT  C(101)  C(308)  C(313)  C(312)  C(311)  C(310)  C(309)  AND 
CONT  C(101)  C(314)  C(315)  C(316)  C(317)  C(318)  C(319)  AND 
CONT  C(101)  C(314)  C(319)  C(318)  C(317)  C(316)  C(315)  AND 
CONT  C(201)  C(408)  C(409)  C(410)  C(411)  C(412)  C(413)  AND 
CONT  C(201)  C(408)  C(413)  C(412)  C(411)  C(410)  C(409)  AND 
CONT  C(201)  C(414)  C(415)  C(416)  C(417)  C(418)  C(419)  AND 
CONT  C(201)  C(414)  C(419)  C(418)  C(417)  C(416)  C(415) 
REM 
REM TBA 
REM 
SAME  N(501)  C(502)  C(503)  C(504)  C(505)  AND 
CONT  N(501)  C(506)  C(507)  C(508)  C(509)  AND 
CONT  N(501)  C(510)  C(511)  C(512)  C(513)  AND 
CONT  N(501)  C(514)  C(515)  C(516)  C(517)  AND 
CONT  N(501)  C(606)  C(607)  C(608)  C(609)  AND 
CONT  N(501)  C(610)  C(611)  C(612)  C(613)  AND 
CONT  N(501)  C(514)  C(515)  C(617)  C(618) 
SIMU  0.005   N(501)  C(502)  C(503)  C(504)  C(505)  AND 
CONT  N(501)  C(506)  C(507)  C(508)  C(509)  AND 
CONT  N(501)  C(510)  C(511)  C(512)  C(513)  AND 
CONT  N(501)  C(514)  C(515)  C(516)  C(517)  AND 
CONT  N(501)  C(606)  C(607)  C(608)  C(609)  AND 
CONT  N(501)  C(610)  C(611)  C(612)  C(613)  AND 
CONT  N(501)  C(514)  C(515)  C(617)  C(618) 
DELU  0.005   N(501)  C(502)  C(503)  C(504)  C(505)  AND 
CONT  N(501)  C(506)  C(507)  C(508)  C(509)  AND 
CONT  N(501)  C(510)  C(511)  C(512)  C(513)  AND 
CONT  N(501)  C(514)  C(515)  C(516)  C(517)  AND 
CONT  N(501)  C(606)  C(607)  C(608)  C(609)  AND 
CONT  N(501)  C(610)  C(611)  C(612)  C(613)  AND 
CONT  N(501)  C(514)  C(515)  C(617)  C(618) 
END                                                                             
;