#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/42/7104212.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7104212
loop_
_publ_author_name
'Yanai, Hikaru'
'Taguchi, Takeo'
_publ_section_title
;
 Novel defluorinative alkylation of trifluoroacetaldehyde N,O-acetal
 derivatives and its application to multi-component reaction.
;
_journal_issue                   9
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1034
_journal_page_last               1036
_journal_paper_doi               10.1039/b817599c
_journal_volume                  34
_journal_year                    2009
_chemical_formula_moiety         'C19 H21 F2 N O'
_chemical_formula_sum            'C19 H21 F2 N O'
_chemical_formula_weight         317.37
_chemical_name_common
;3-Benzyl-2-butyl-2-(difluoromethyl)-2,3-dihydro-1,3-
benzoxazole
;
_chemical_name_systematic
;
3-Benzyl-2-butyl-2-(difluoromethyl)-2,3-dihydro-1,3-benzoxazole
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             '12 September 08'
_audit_creation_method           'SHELXL97 '
_cell_angle_alpha                97.534(11)
_cell_angle_beta                 97.342(11)
_cell_angle_gamma                113.009(8)
_cell_formula_units_Z            2
_cell_length_a                   8.979(6)
_cell_length_b                   9.368(6)
_cell_length_c                   10.983(13)
_cell_measurement_reflns_used    2179
_cell_measurement_temperature    90
_cell_measurement_theta_max      27.33
_cell_measurement_theta_min      2.51
_cell_volume                     826.5(12)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      90
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.813
_diffrn_measured_fraction_theta_max 0.813
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'multilayer confocal mirror'
_diffrn_radiation_source         'fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0513
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3929
_diffrn_reflns_theta_full        27.42
_diffrn_reflns_theta_max         27.42
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9870
_exptl_absorpt_correction_T_min  0.9734
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3073
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0577
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1169P)²+0.2045P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1747
_refine_ls_wR_factor_ref         0.1877
_reflns_number_gt                2426
_reflns_number_total             3073
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b817599c.txt
_cod_data_source_block           2ca
_cod_original_sg_symbol_Hall     '-P 1 '
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               7104212
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.7603(2) 0.36960(19) 0.66935(17) 0.0182(4) Uani 1 1 d . . .
O1 O 0.89987(17) 0.34985(16) 0.85360(14) 0.0210(4) Uani 1 1 d . . .
C4 C 1.0182(2) 0.6850(2) 0.8333(2) 0.0215(5) Uani 1 1 d . . .
H4A H 1.0984 0.6441 0.8660 0.026 Uiso 1 1 calc R . .
H4B H 1.0098 0.6729 0.7415 0.026 Uiso 1 1 calc R . .
C1 C 0.7842(2) 0.4121(2) 0.8056(2) 0.0184(5) Uani 1 1 d . . .
C2 C 0.6237(3) 0.3130(3) 0.8448(2) 0.0242(5) Uani 1 1 d . . .
H2 H 0.5908 0.1980 0.8117 0.029 Uiso 1 1 calc R . .
C5 C 1.0812(3) 0.8597(2) 0.8916(2) 0.0278(6) Uani 1 1 d . . .
H5A H 1.0052 0.9023 0.8538 0.033 Uiso 1 1 calc R . .
H5B H 1.0804 0.8707 0.9824 0.033 Uiso 1 1 calc R . .
C3 C 0.8498(2) 0.5876(2) 0.8616(2) 0.0211(5) Uani 1 1 d . . .
H3A H 0.8585 0.6013 0.9535 0.025 Uiso 1 1 calc R . .
H3B H 0.7700 0.6286 0.8284 0.025 Uiso 1 1 calc R . .
C6 C 1.2545(3) 0.9569(3) 0.8736(3) 0.0321(6) Uani 1 1 d . . .
H6A H 1.3306 0.9161 0.9116 0.048 Uiso 1 1 calc R . .
H6B H 1.2893 1.0677 0.9136 0.048 Uiso 1 1 calc R . .
H6C H 1.2554 0.9495 0.7839 0.048 Uiso 1 1 calc R . .
C8 C 0.5883(2) 0.3433(2) 0.4663(2) 0.0174(5) Uani 1 1 d . . .
C9 C 0.6090(2) 0.3822(2) 0.3514(2) 0.0210(5) Uani 1 1 d . . .
H9 H 0.6972 0.4780 0.3466 0.025 Uiso 1 1 calc R . .
C7 C 0.7025(2) 0.4536(2) 0.5847(2) 0.0190(5) Uani 1 1 d . . .
H7A H 0.7988 0.5352 0.5622 0.023 Uiso 1 1 calc R . .
H7B H 0.6438 0.5081 0.6284 0.023 Uiso 1 1 calc R . .
C10 C 0.5024(3) 0.2830(3) 0.2416(2) 0.0246(5) Uani 1 1 d . . .
H10 H 0.5178 0.3109 0.1626 0.030 Uiso 1 1 calc R . .
C12 C 0.3520(3) 0.1039(2) 0.3642(2) 0.0295(6) Uani 1 1 d . . .
H12 H 0.2634 0.0084 0.3690 0.035 Uiso 1 1 calc R . .
C13 C 0.4585(3) 0.2024(2) 0.4728(2) 0.0238(5) Uani 1 1 d . . .
H13 H 0.4433 0.1741 0.5517 0.029 Uiso 1 1 calc R . .
C11 C 0.3736(3) 0.1433(3) 0.2492(2) 0.0274(5) Uani 1 1 d . . .
H11 H 0.3005 0.0749 0.1750 0.033 Uiso 1 1 calc R . .
C16 C 0.9127(2) 0.2648(2) 0.5289(2) 0.0202(5) Uani 1 1 d . . .
H16 H 0.8603 0.2757 0.4521 0.024 Uiso 1 1 calc R . .
C15 C 0.8755(2) 0.3107(2) 0.6423(2) 0.0171(5) Uani 1 1 d . . .
C14 C 0.9559(2) 0.2974(2) 0.7526(2) 0.0179(5) Uani 1 1 d . . .
C17 C 1.0308(3) 0.2016(2) 0.5329(2) 0.0231(5) Uani 1 1 d . . .
H17 H 1.0576 0.1673 0.4567 0.028 Uiso 1 1 calc R . .
C19 C 1.0736(2) 0.2375(2) 0.7586(2) 0.0217(5) Uani 1 1 d . . .
H19 H 1.1278 0.2303 0.8362 0.026 Uiso 1 1 calc R . .
C18 C 1.1093(2) 0.1877(2) 0.6441(2) 0.0224(5) Uani 1 1 d . . .
H18 H 1.1885 0.1439 0.6432 0.027 Uiso 1 1 calc R . .
F1 F 0.50205(15) 0.35606(16) 0.79926(14) 0.0301(4) Uani 1 1 d . . .
F2 F 0.64008(16) 0.33978(17) 0.97089(13) 0.0343(4) Uani 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 N1 C1 107.78(16) . . ?
C15 N1 C7 121.23(19) . . ?
C1 N1 C7 122.71(17) . . ?
C14 O1 C1 107.41(17) . . ?
C5 C4 C3 111.94(18) . . ?
C5 C4 H4A 109.2 . . ?
C3 C4 H4A 109.2 . . ?
C5 C4 H4B 109.2 . . ?
C3 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
O1 C1 N1 104.75(15) . . ?
O1 C1 C3 109.64(16) . . ?
N1 C1 C3 116.35(18) . . ?
O1 C1 C2 104.14(18) . . ?
N1 C1 C2 107.99(16) . . ?
C3 C1 C2 112.97(18) . . ?
F2 C2 F1 106.42(17) . . ?
F2 C2 C1 111.16(17) . . ?
F1 C2 C1 109.5(2) . . ?
F2 C2 H2 109.9 . . ?
F1 C2 H2 109.9 . . ?
C1 C2 H2 109.9 . . ?
C6 C5 C4 112.85(19) . . ?
C6 C5 H5A 109.0 . . ?
C4 C5 H5A 109.0 . . ?
C6 C5 H5B 109.0 . . ?
C4 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C1 C3 C4 113.25(17) . . ?
C1 C3 H3A 108.9 . . ?
C4 C3 H3A 108.9 . . ?
C1 C3 H3B 108.9 . . ?
C4 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C9 C8 C13 119.24(19) . . ?
C9 C8 C7 120.38(19) . . ?
C13 C8 C7 120.4(2) . . ?
C8 C9 C10 121.0(2) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
N1 C7 C8 112.12(17) . . ?
N1 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
N1 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C11 C10 C9 119.3(2) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C11 C12 C13 120.5(2) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C8 120.0(2) . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
C12 C11 C10 120.0(2) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C15 C16 C17 117.0(2) . . ?
C15 C16 H16 121.5 . . ?
C17 C16 H16 121.5 . . ?
C14 C15 C16 120.4(2) . . ?
C14 C15 N1 108.57(19) . . ?
C16 C15 N1 131.0(2) . . ?
C19 C14 C15 123.4(2) . . ?
C19 C14 O1 125.9(2) . . ?
C15 C14 O1 110.66(19) . . ?
C18 C17 C16 121.9(2) . . ?
C18 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
C14 C19 C18 116.5(2) . . ?
C14 C19 H19 121.8 . . ?
C18 C19 H19 121.8 . . ?
C17 C18 C19 120.8(2) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C15 1.395(3) . ?
N1 C1 1.462(3) . ?
N1 C7 1.463(3) . ?
O1 C14 1.385(3) . ?
O1 C1 1.453(3) . ?
C4 C5 1.523(3) . ?
C4 C3 1.527(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C1 C3 1.521(3) . ?
C1 C2 1.530(3) . ?
C2 F2 1.353(3) . ?
C2 F1 1.365(3) . ?
C2 H2 1.0000 . ?
C5 C6 1.519(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C8 C9 1.374(3) . ?
C8 C13 1.395(3) . ?
C8 C7 1.512(3) . ?
C9 C10 1.396(3) . ?
C9 H9 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C10 C11 1.388(3) . ?
C10 H10 0.9500 . ?
C12 C11 1.378(4) . ?
C12 C13 1.385(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C11 H11 0.9500 . ?
C16 C15 1.387(3) . ?
C16 C17 1.402(3) . ?
C16 H16 0.9500 . ?
C15 C14 1.376(3) . ?
C14 C19 1.375(3) . ?
C17 C18 1.378(4) . ?
C17 H17 0.9500 . ?
C19 C18 1.403(3) . ?
C19 H19 0.9500 . ?
C18 H18 0.9500 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139180923
