Synthesis of Trifluoromethylated Pyrazolidines by [3+2] Cycloaddition
Peng, Xiansha; Huang, Danfeng; Wang, Ke-Hu; Wang, Yalin; Wang, Juanjuan; Su, Yingpeng; Hu, Yulai; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB01299C

data_7155752
_publ_section_title
;
 Synthesis of Trifluoromethylated Pyrazolidines by [3+2] Cycloaddition
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB01299C
_journal_year                    2017
_chemical_formula_moiety         'C10 H7 F3 N2'
_chemical_formula_sum            'C10 H7 F3 N2'
_chemical_formula_weight         212.18
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-12-02
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.24 svn.r3356 for OlexSys, GUI svn.r5267)
;
_audit_update_record
;
2017-03-13 deposited with the CCDC.
2017-06-27 downloaded from the CCDC.
;
_cell_angle_alpha                80.533(7)
_cell_angle_beta                 87.495(6)
_cell_angle_gamma                89.524(6)
_cell_formula_units_Z            8
_cell_length_a                   9.9013(7)
_cell_length_b                   9.9393(8)
_cell_length_c                   21.0212(16)
_cell_measurement_reflns_used    1979
_cell_measurement_temperature    283(4)
_cell_measurement_theta_max      20.8050
_cell_measurement_theta_min      3.6760
_cell_volume                     2038.6(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      283(4)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9975
_diffrn_measured_fraction_theta_max 0.8819
_diffrn_measurement_details
;
  1 omega  -53.00   14.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055   79.0000 -176.0000 67

  2 omega  -19.00   50.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055   77.0000 -150.0000 69

  3 omega  -13.00   64.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -99.0000  -60.0000 77

  4 omega  -48.00   38.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000  -30.0000 86

  5 omega   -9.00   95.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   77.0000   90.0000 104
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0625924000
_diffrn_orient_matrix_UB_12      -0.0126585000
_diffrn_orient_matrix_UB_13      0.0150758000
_diffrn_orient_matrix_UB_21      0.0323125000
_diffrn_orient_matrix_UB_22      0.0466685000
_diffrn_orient_matrix_UB_23      -0.0250999000
_diffrn_orient_matrix_UB_31      -0.0134076000
_diffrn_orient_matrix_UB_32      0.0538161000
_diffrn_orient_matrix_UB_33      0.0177503000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0686
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13541
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         3.383
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55509
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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    1.383
_exptl_crystal_description       plate
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     640
_refine_ls_number_reflns         8011
_refine_ls_number_restraints     162
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.1737
_refine_ls_R_factor_gt           0.0977
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1260P)^2^+0.7908P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2572
_refine_ls_wR_factor_ref         0.3188
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3663
_reflns_number_total             8011
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob01299c2.cif
_cod_data_source_block           pxs_2
_cod_database_code               7155752
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(F5') \\sim Ueq, Uanis(F8) \\sim Ueq, Uanis(F4') \\sim Ueq, Uanis(F7)
\\sim Ueq, Uanis(F6') \\sim Ueq, Uanis(F9) \\sim Ueq, Uanis(F6) \\sim Ueq,
Uanis(F7') \\sim Ueq, Uanis(F4) \\sim Ueq, Uanis(F9') \\sim Ueq, Uanis(F5)
\\sim Ueq, Uanis(F8') \\sim Ueq, Uanis(F11') \\sim Ueq, Uanis(F12) \\sim Ueq,
Uanis(F10') \\sim Ueq, Uanis(F10) \\sim Ueq, Uanis(F12') \\sim Ueq, Uanis(F11)
\\sim Ueq, Uanis(F1') \\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(F2') \\sim Ueq,
Uanis(F3) \\sim Ueq, Uanis(F2) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C12) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C15)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: F7'(0.4) F8'(0.4) F9'(0.4) F10'(0.4) F11'(0.4) F12'(0.4) F4'(0.5)
 F5'(0.5) F6'(0.5) F1'(0.35) F2'(0.5) F5(0.6) F1(0.65) F9(0.5) F3(0.5) F7(0.5)
 F11(0.6) F4(0.6) F6(0.6) F8(0.5) F10(0.6) F12(0.6)
4.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C28(H28), N5(H5),
 C31(H31), C32(H32), C33(H33), C34(H34), C35(H35), C38(H38), N7(H7), C11(H11),
 C12(H12), C13(H13), C14(H14), C15(H15), C18(H18), N1(H1), C1(H1A), C2(H2),
 C3(H3A), C4(H4), C5(H5A), C8(H8)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-11-29
_olex2_submission_special_instructions 'No special instructions were received'