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_1520628
_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(C13 H12 O), C16 H36 N, F'
_chemical_formula_sum            'C55 H72 F N O3'
_chemical_formula_weight         814.18
_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             13-04-30
_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                81.8444(6)
_cell_angle_beta                 89.1604(6)
_cell_angle_gamma                78.5486(7)
_cell_formula_units_Z            2
_cell_length_a                   9.4953(1)
_cell_length_b                   12.1501(2)
_cell_length_c                   21.4618(4)
_cell_measurement_reflns_used    10032
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     2401.96(7)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_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 0.986
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.022
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            40263
_diffrn_reflns_theta_full        25.087
_diffrn_reflns_theta_max         27.568
_diffrn_reflns_theta_min         5.114
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.65
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.126
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             884.000
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.53
_refine_diff_density_min         -0.35
_refine_ls_extinction_coef       450(90)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   0.9966
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     597
_refine_ls_number_reflns         8998
_refine_ls_number_restraints     256
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0480
_refine_ls_shift/su_max          0.0005931
_refine_ls_shift/su_mean         0.0000687
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.96P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1278
_refine_ls_wR_factor_gt          0.1166
_refine_ls_wR_factor_ref         0.1277
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              15
_reflns_limit_k_min              -15
_reflns_limit_l_max              27
_reflns_limit_l_min              0
_reflns_number_gt                7316
_reflns_number_total             10827
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.44
_oxford_diffrn_Wilson_scale      0.55
_oxford_refine_ls_r_factor_ref   0.0611
_oxford_refine_ls_scale          1.317(6)
_oxford_reflns_number_all        8999
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 065ggke01
_cod_data_source_file            c5sc01812a2.cif
_cod_data_source_block           2k
_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_formula_sum        'C55 H72 F1 N1 O3'
_cod_database_code               1520628
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT EXTPARAM 
EQUIV PART(1001,OCC) PART(1002,OCC) 
WEIGHT -1 PART(1002,OCC) 
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 C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  59,X'S) H   ( 591,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  61,X'S) H   ( 611,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   (  20,X'S) H   ( 201,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) 
RIDE C   (  31,X'S) H   ( 311,X'S) 
RIDE C   (  33,X'S) H   ( 331,X'S) 
RIDE C   (  34,X'S) H   ( 341,X'S) 
RIDE C   (  35,X'S) H   ( 351,X'S) 
RIDE C   (  36,X'S) H   ( 361,X'S) 
RIDE C   (  37,X'S) H   ( 371,X'S) 
RIDE C   (  39,X'S) H   ( 391,X'S) 
RIDE C   (  40,X'S) H   ( 401,X'S) 
RIDE C   (  41,X'S) H   ( 411,X'S) 
RIDE C   (  42,X'S) H   ( 421,X'S) 
RIDE C   (  43,X'S) H   ( 431,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   ( 551,X'S) 
RIDE C   (  56,X'S) H   ( 561,X'S) 
RIDE C   (  57,X'S) H   ( 571,X'S) 
RIDE C   (  81,X'S) H   ( 811,X'S) H   ( 812,X'S) 
RIDE C   (  60,X'S) H   ( 601,X'S) 
RIDE C   (  83,X'S) H   ( 831,X'S) H   ( 832,X'S) H   ( 833,X'S) 
RIDE C   (  62,X'S) H   ( 621,X'S) 
RIDE C   (  63,X'S) H   ( 631,X'S) 
RIDE C   (  72,X'S) H   ( 721,X'S) H   ( 722,X'S) 
RIDE C   (  73,X'S) H   ( 731,X'S) H   ( 732,X'S) 
RIDE C   (  74,X'S) H   ( 741,X'S) H   ( 742,X'S) 
RIDE C   (  75,X'S) H   ( 753,X'S) H   ( 752,X'S) H   ( 751,X'S) 
RIDE C   (  76,X'S) H   ( 762,X'S) H   ( 761,X'S) 
RIDE C   (  77,X'S) H   ( 771,X'S) H   ( 772,X'S) 
RIDE C   (  78,X'S) H   ( 781,X'S) H   ( 782,X'S) 
RIDE C   (  79,X'S) H   ( 793,X'S) H   ( 792,X'S) H   ( 791,X'S) 
RIDE C   (  80,X'S) H   ( 801,X'S) H   ( 802,X'S) 
RIDE C   ( 117,X'S) H   (1171,X'S) 
RIDE C   (  82,X'S) H   ( 821,X'S) H   ( 822,X'S) 
RIDE C   ( 115,X'S) H   (1151,X'S) 
RIDE C   (  84,X'S) H   ( 841,X'S) H   ( 842,X'S) 
RIDE C   (  85,X'S) H   ( 851,X'S) H   ( 852,X'S) 
RIDE C   (  86,X'S) H   ( 862,X'S) H   ( 861,X'S) 
RIDE C   (  87,X'S) H   ( 873,X'S) H   ( 872,X'S) H   ( 871,X'S) 
RIDE C   ( 116,X'S) H   (1161,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   ( 114,X'S) H   (1141,X'S) 
RIDE C   ( 113,X'S) H   (1131,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
SAME C(11)  C(12)  C(17)  C(16)  C(15)  C(14)  C(13) AND 
CONT C(11)  C(12)  C(13)  C(14)  C(15)  C(16)  C(17) AND 
CONT C(11)  C(112)  C(117)  C(116)  C(115)  C(114)  C(113) AND 
CONT C(11)  C(112)  C(113)  C(114)  C(115)  C(116)  C(117) 
SIMU 0.01   C(11)  C(12)  C(17)  C(16)  C(15)  C(14)  C(13) AND 
CONT C(11)  C(12)  C(13)  C(14)  C(15)  C(16)  C(17) AND 
CONT C(11)  C(112)  C(117)  C(116)  C(115)  C(114)  C(113) AND 
CONT C(11)  C(112)  C(113)  C(114)  C(115)  C(116)  C(117) 
DELU 0.01   C(11)  C(12)  C(17)  C(16)  C(15)  C(14)  C(13) AND 
CONT C(11)  C(12)  C(13)  C(14)  C(15)  C(16)  C(17) AND 
CONT C(11)  C(112)  C(117)  C(116)  C(115)  C(114)  C(113) AND 
CONT C(11)  C(112)  C(113)  C(114)  C(115)  C(116)  C(117) 
END                                                                             
;