Amine-catalyzed and functional group-controlled chemo- and regioselective synthesis of multi-functionalized CF3-benzene via a metal-free process
Peng, Fu; Zhao, Qian; Huang, Wei; Liu, Shuai-Jiang; Zhong, Ya-Jun; Mao, Qing; Zhang, Nan; He, Gu; Han, Bo; Green Chemistry  (2019) –; doi:10.1039/C9GC02694K

data_7234745
_publ_section_title
;
 Amine-catalyzed and functional group-controlled chemo- and regioselective
 synthesis of multi-functionalized CF3-benzene via a metal-free process
;
_journal_name_full               'Green Chemistry'
_journal_paper_doi               10.1039/C9GC02694K
_journal_year                    2019
_chemical_formula_moiety         'C23 H17 F3 O3'
_chemical_formula_sum            'C23 H17 F3 O3'
_chemical_formula_weight         398.36
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-01-19
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2019-02-20 deposited with the CCDC.    2019-10-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.2218(6)
_cell_length_b                   13.2420(4)
_cell_length_c                   17.2998(5)
_cell_measurement_reflns_used    5114
_cell_measurement_temperature    293.8(2)
_cell_measurement_theta_max      72.3270
_cell_measurement_theta_min      4.1440
_cell_volume                     3945.2(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.8(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details
;
  1 omega    9.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.7921   77.0000  -60.0000 94

  2 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.7921   57.0000 -180.0000 84

  3 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.7921   57.0000   60.0000 84

  4 omega    0.00   26.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.7921   94.0000 -158.1318 26

  5 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.7921 -125.0000  -30.0000 66

  6 omega  -33.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.7921  -38.0000   60.0000 88

  7 omega   38.00   88.00   1.0000    1.4600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 50

  8 omega   43.00   98.00   1.0000    1.4600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 55

  9 omega   42.00   92.00   1.0000    1.4600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 50

 10 omega   70.00  100.00   1.0000    1.4600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 30

 11 omega   49.00   88.00   1.0000    1.4600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 39

 12 omega   42.00  115.00   1.0000    1.4600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -150.0000 73
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0162154000
_diffrn_orient_matrix_UB_12      -0.0396108000
_diffrn_orient_matrix_UB_13      0.0821760000
_diffrn_orient_matrix_UB_21      0.0871094000
_diffrn_orient_matrix_UB_22      0.0228495000
_diffrn_orient_matrix_UB_23      -0.0106249000
_diffrn_orient_matrix_UB_31      -0.0124981000
_diffrn_orient_matrix_UB_32      0.1069276000
_diffrn_orient_matrix_UB_33      0.0326367000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11346
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.427
_diffrn_reflns_theta_min         4.928
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.909
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42067
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.5
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.125
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3809
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0650
_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^)+(0.0996P)^2^+0.9268P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1607
_refine_ls_wR_factor_ref         0.1709
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3139
_reflns_number_total             3809
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9gc02694k2.cif
_cod_data_source_block           lq-hb-zq-02062
_cod_original_cell_volume        3945.3(2)
_cod_database_code               7234745
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 Secondary CH2 refined with riding coordinates:
 C21(H00a,H00c)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H00B), C13(H00F), C5(H00H), C1(H00I), C19(H00J), C15(H00K), C2(H00M),
 C3(H00N), C4(H00O), C17(H00P), C18(H00Q), C16(H00R)
2.c Idealised Me refined as rotating group:
 C22(H00d,H00e,H00g)
;
_shelx_res_checksum              43605
_olex2_date_sample_data_collection 2018-01-19
_olex2_submission_special_instructions 'No special instructions were received'