Domino Assembly of Trifluoromethylated N,O-Heterocycles by the Reaction of Fluorinated α-Bromoenones with Amino Alcohols.
Rulev, Alexander Yu; Romanov, Alexey R.; Kondrashov, Evgeniy V.; Ushakov, Igor A.; Vashchenko, Alexander V.; Muzalevskiy, Vasiliy M.; Nenajdenko, Valentine G.; The Journal of organic chemistry 81 (2016) 10029–10034; doi:10.1021/acs.joc.6b01927

data_4037293
_publ_section_title
;
 Domino Assembly of Trifluoromethylated N,O-Heterocycles by the Reaction
 of Fluorinated \a-Bromoenones with Amino Alcohols.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10029
_journal_page_last               10034
_journal_paper_doi               10.1021/acs.joc.6b01927
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C13 H14 F3 N O3'
_chemical_formula_sum            'C13 H14 F3 N O3'
_chemical_formula_weight         289.25
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2016-04-29
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-05-17 # Formatted by publCIF

;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.7857(4)
_cell_length_b                   10.2761(6)
_cell_length_c                   22.0932(13)
_cell_measurement_reflns_used    374
_cell_measurement_temperature    297.1
_cell_measurement_theta_max      26.25
_cell_measurement_theta_min      2.15
_cell_volume                     1313.54(14)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      297.1
_diffrn_detector_area_resol_mean 0.80
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  none
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            38660
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.252
_diffrn_reflns_theta_min         2.186
_diffrn_source                   IuS
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6377
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1458 before and 0.0671 after correction.
The Ratio of minimum to maximum transmission is 0.8556.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_description       needle
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.86
_exptl_crystal_size_mid          0.317
_exptl_crystal_size_min          0.089
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 845 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_coef       0.015(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2633
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0366
_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^)+(0.0349P)^2^+0.4309P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0825
_refine_ls_wR_factor_ref         0.0867
_reflns_Friedel_coverage         0.689
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                2273
_reflns_number_total             2633
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01927_si_004.cif
_cod_data_source_block           a_final
_cod_database_code               4037293
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.896
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C11(H11), C12(H12), C13(H13)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              38211
_shelx_hkl_checksum              25061
_olex2_submission_special_instructions 'No special instructions were received'