“Goldilocks Effect” of Water in Lewis-Brønsted Acid and Base Catalysis
Barron, Benedict J.; Wong, Wing-Tak; Chiu, Pauline; Hii, King Kuok; ACS Catalysis 6 (2016) 4189–; doi:10.1021/acscatal.6b00800

data_4513886
_publ_section_title
;
 &#x201C;Goldilocks Effect&#x201D; of Water in Lewis-Br\/onsted Acid and
 Base Catalysis
;
_journal_issue                   7
_journal_name_full               'ACS Catalysis'
_journal_page_first              4189
_journal_paper_doi               10.1021/acscatal.6b00800
_journal_volume                  6
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H16 F3 N3 O3'
_chemical_formula_sum            'C14 H16 F3 N3 O3'
_chemical_formula_weight         331.30
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-07-30
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.8832(3)
_cell_length_b                   15.6825(11)
_cell_length_c                   19.6960(13)
_cell_measurement_reflns_used    9873
_cell_measurement_temperature    100
_cell_measurement_theta_max      74.765
_cell_measurement_theta_min      3.603
_cell_volume                     1508.34(17)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2014)'
_computing_data_collection       'APEX2  v2014.11-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2014)'
_computing_molecular_graphics    'Mercury (Macrae et. al, 2008)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.99
_diffrn_detector                 'Bruker Photon100 CMOS area detector'
_diffrn_detector_area_resol_mean 1024
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture microsource'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10915
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        66.536
_diffrn_reflns_theta_max         66.536
_diffrn_reflns_theta_min         5.642
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.112
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1467 before and 0.0826 after correction.
The Ratio of minimum to maximum transmission is 0.5825.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_recrystallization_method
'The crystal was recrystallised from an ethyl acetate solution.'
_exptl_crystal_size_max          0.687
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.094
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details
;
 Flack x determined using 1012 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner (2013) Acta Cryst. B69, 249-259).
;
_refine_ls_abs_structure_Flack   0.15(6)
_refine_ls_extinction_coef       0.0061(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         2634
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0423
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0516P)^2^+0.8336P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1080
_refine_ls_wR_factor_ref         0.1087
_reflns_Friedel_coverage         0.671
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                2585
_reflns_number_total             2634
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs6b00800_si_002.cif
_cod_data_source_block           cu_chem0109_b0ma
_cod_depositor_comments          'Adding full bibliography for 4513886.cif.'
_cod_database_code               4513886
_shelx_estimated_absorpt_t_max   0.903
_shelx_estimated_absorpt_t_min   0.515
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3A), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C14(H14A,H14B,H14C)
;
_shelx_shelxl_version_number     2014/7
_olex2_exptl_crystal_mounting_method
;
The crystal was coated in a very thin layer of paraton-N
oil and then mounted on a Cryo-Loop.
;
_olex2_submission_special_instructions 'No special instructions were received'