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_1520626
_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         'C16 H36 N, 3(C11 H14 O2), F, H2 O'
_chemical_formula_sum            'C49 H80 F N O7'
_chemical_formula_weight         814.17
_chemical_melting_point          ?
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             13-04-24
_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                 92.0698(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.75510(1)
_cell_length_b                   12.74630(1)
_cell_length_c                   22.1115(2)
_cell_measurement_reflns_used    35528
_cell_measurement_temperature    150
_cell_measurement_theta_max      77
_cell_measurement_theta_min      3
_cell_volume                     2465.93(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 0.998
_diffrn_measured_fraction_theta_max 0.993
_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       10
_diffrn_reflns_limit_h_min       -11
_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            53899
_diffrn_reflns_theta_full        75.196
_diffrn_reflns_theta_max         76.731
_diffrn_reflns_theta_min         3.467
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.589
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.096
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             892
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.33
_refine_diff_density_min         -0.16
_refine_ls_abs_structure_details 'Flack (1983), 4705 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.31(7)
_refine_ls_extinction_coef       83(8)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   0.9982
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     544
_refine_ls_number_reflns         9828
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0296
_refine_ls_shift/su_max          0.0006168
_refine_ls_shift/su_mean         0.0000430
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.27P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0797
_refine_ls_wR_factor_gt          0.0793
_refine_ls_wR_factor_ref         0.0797
_reflns_limit_h_max              10
_reflns_limit_h_min              -11
_reflns_limit_k_max              15
_reflns_limit_k_min              0
_reflns_limit_l_max              27
_reflns_limit_l_min              -27
_reflns_number_gt                9682
_reflns_number_total             9870
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.10
_oxford_diffrn_Wilson_scale      0.02
_oxford_refine_ls_r_factor_ref   0.0300
_oxford_refine_ls_scale          7.22(11)
_oxford_reflns_number_all        9828
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 008gwp12
_cod_data_source_file            c5sc01812a2.cif
_cod_data_source_block           2i
_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_cell_volume        2465.93(4)
_cod_original_sg_symbol_H-M      'P c '
_cod_original_formula_sum        'C49 H80 F1 N1 O7'
_cod_database_code               1520626
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
CONT EXTPARAM 
EQUIV PART(1001,OCC) PART(1002,OCC) 
WEIGHT -1 PART(1002,OCC) 
RIDE O   (   4,X'S) H   (  42,X'S) H   (  41,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) 
RIDE C   ( 109,X'S) H   (1091,X'S) 
RIDE C   ( 110,X'S) H   (1103,X'S) H   (1101,X'S) H   (1102,X'S) 
RIDE C   ( 111,X'S) H   (1112,X'S) H   (1111,X'S) H   (1113,X'S) 
RIDE C   ( 112,X'S) H   (1121,X'S) H   (1123,X'S) H   (1122,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   ( 209,X'S) H   (2091,X'S) 
RIDE C   ( 210,X'S) H   (2103,X'S) H   (2101,X'S) H   (2102,X'S) 
RIDE C   ( 211,X'S) H   (2111,X'S) H   (2113,X'S) H   (2112,X'S) 
RIDE C   ( 212,X'S) H   (2122,X'S) H   (2123,X'S) H   (2121,X'S) 
RIDE C   ( 306,X'S) H   (3061,X'S) 
RIDE C   ( 307,X'S) H   (3071,X'S) 
RIDE C   ( 308,X'S) H   (3081,X'S) 
RIDE C   ( 309,X'S) H   (3091,X'S) 
RIDE C   ( 310,X'S) H   (3102,X'S) H   (3103,X'S) H   (3101,X'S) 
RIDE C   ( 311,X'S) H   (3113,X'S) H   (3111,X'S) H   (3112,X'S) 
RIDE C   ( 312,X'S) H   (3121,X'S) H   (3123,X'S) H   (3122,X'S) 
RIDE C   ( 402,X'S) H   (4022,X'S) H   (4021,X'S) 
RIDE C   ( 403,X'S) H   (4032,X'S) H   (4031,X'S) 
RIDE C   ( 404,X'S) H   (4041,X'S) H   (4042,X'S) 
RIDE C   ( 405,X'S) H   (4052,X'S) H   (4053,X'S) H   (4051,X'S) 
RIDE C   ( 406,X'S) H   (4062,X'S) H   (4061,X'S) 
RIDE C   ( 407,X'S) H   (4072,X'S) H   (4071,X'S) 
RIDE C   ( 408,X'S) H   (4081,X'S) H   (4082,X'S) 
RIDE C   ( 409,X'S) H   (4091,X'S) H   (4093,X'S) H   (4092,X'S) 
RIDE C   ( 410,X'S) H   (4102,X'S) H   (4101,X'S) 
RIDE C   ( 411,X'S) H   (4111,X'S) H   (4112,X'S) 
RIDE C   ( 412,X'S) H   (4121,X'S) H   (4122,X'S) 
RIDE C   ( 413,X'S) H   (4131,X'S) H   (4132,X'S) H   (4133,X'S) 
RIDE C   ( 414,X'S) H   (4141,X'S) H   (4142,X'S) 
RIDE C   ( 415,X'S) H   (4151,X'S) H   (4152,X'S) 
CONT H   (4153,X'S) H   (4154,X'S) 
RIDE C   ( 416,X'S) H   (4161,X'S) H   (4162,X'S) 
RIDE C   ( 417,X'S) H   (4172,X'S) H   (4173,X'S) H   (4171,X'S) 
RIDE C   ( 418,X'S) H   (4181,X'S) H   (4182,X'S) 
RIDE C   ( 419,X'S) H   (4191,X'S) H   (4192,X'S) H   (4193,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) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;