#------------------------------------------------------------------------------
#$Date: 2020-10-06 14:23:41 +0300 (Tue, 06 Oct 2020) $
#$Revision: 258018 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/08/7240840.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_7240840
loop_
_publ_author_name
'Bao, Kun'
'Wei, Jun'
'Yan, Huihui'
'Sheng, Rong'
_publ_section_title
;
 Visible-light promoted three-component tandem reaction to synthesize
 difluoromethylated oxazolidin-2-imine
;
_journal_issue                   43
_journal_name_full               'RSC Advances'
_journal_page_first              25947
_journal_page_last               25951
_journal_paper_doi               10.1039/D0RA04729E
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C25 H21 F5 N2 O'
_chemical_formula_sum            'C25 H21 F5 N2 O'
_chemical_formula_weight         460.44
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-04-21 deposited with the CCDC.	2020-06-25 downloaded from the CCDC.
;
_cell_angle_alpha                76.082(4)
_cell_angle_beta                 73.273(4)
_cell_angle_gamma                77.314(4)
_cell_formula_units_Z            2
_cell_length_a                   8.6898(10)
_cell_length_b                   11.1725(11)
_cell_length_c                   12.0639(13)
_cell_measurement_reflns_used    5161
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      26.25
_cell_measurement_theta_min      2.48
_cell_volume                     1074.4(2)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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_temperature      170.0
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_unetI/netI     0.0635
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11994
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.421
_diffrn_reflns_theta_min         2.356
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1344 before and 0.0833 after correction.
The Ratio of minimum to maximum transmission is 0.7650.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_description       block
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.564
_refine_diff_density_min         -0.534
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4333
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0663
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0849P)²+1.1044P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1787
_refine_ls_wR_factor_ref         0.1915
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3386
_reflns_number_total             4333
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ra04729e2.cif
_cod_data_source_block           190925_bk_4_94a_0m
_cod_depositor_comments          'Adding full bibliography for 7240840.cif.'
_cod_database_code               7240840
_shelx_shelxl_version_number     2016/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.966
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C11(H11A,H11B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.3348(3) 0.9892(2) 0.2950(4) 0.1270(16) Uani 1 1 d . . . . .
F2 F 0.1244(3) 0.92760(19) 0.40312(19) 0.0712(8) Uani 1 1 d . . . . .
F3 F 0.1590(4) 0.9576(2) 0.2217(2) 0.1039(12) Uani 1 1 d . . . . .
F4 F 1.1588(2) 0.33307(17) 0.53092(15) 0.0424(5) Uani 1 1 d . . . . .
F5 F 1.1771(2) 0.18497(15) 0.43662(17) 0.0413(5) Uani 1 1 d . . . . .
O1 O 0.78940(19) 0.43015(16) 0.29223(16) 0.0249(4) Uani 1 1 d . . . . .
N1 N 0.7397(2) 0.23592(19) 0.34148(19) 0.0247(5) Uani 1 1 d . . . . .
N2 N 0.5212(2) 0.40002(19) 0.32877(18) 0.0222(4) Uani 1 1 d . . . . .
C1 C 0.6725(3) 0.3581(2) 0.3224(2) 0.0202(5) Uani 1 1 d . . . . .
C2 C 0.9157(3) 0.2203(2) 0.3004(2) 0.0265(5) Uani 1 1 d . . . . .
H2A H 0.953520 0.196820 0.221704 0.032 Uiso 1 1 calc R . . . .
H2B H 0.968689 0.156623 0.356459 0.032 Uiso 1 1 calc R . . . .
C3 C 0.9482(3) 0.3522(2) 0.2951(2) 0.0217(5) Uani 1 1 d . . . . .
C4 C 0.4636(3) 0.5292(2) 0.3196(2) 0.0208(5) Uani 1 1 d . . . . .
C5 C 0.5122(3) 0.6084(2) 0.3722(2) 0.0254(5) Uani 1 1 d . . . . .
H5 H 0.595414 0.576709 0.413217 0.031 Uiso 1 1 calc R . . . .
C6 C 0.4409(3) 0.7318(3) 0.3651(2) 0.0281(6) Uani 1 1 d . . . . .
H6 H 0.476107 0.784500 0.400762 0.034 Uiso 1 1 calc R . . . .
C7 C 0.3178(3) 0.7806(2) 0.3065(2) 0.0288(6) Uani 1 1 d . . . . .
C8 C 0.2685(3) 0.7029(3) 0.2536(2) 0.0291(6) Uani 1 1 d . . . . .
H8 H 0.185084 0.735087 0.212808 0.035 Uiso 1 1 calc R . . . .
C9 C 0.3402(3) 0.5791(2) 0.2601(2) 0.0266(5) Uani 1 1 d . . . . .
H9 H 0.305344 0.526892 0.223638 0.032 Uiso 1 1 calc R . . . .
C10 C 0.2368(4) 0.9121(3) 0.3047(3) 0.0364(7) Uani 1 1 d . . . . .
C11 C 0.6501(3) 0.1328(2) 0.3652(2) 0.0279(6) Uani 1 1 d . . . . .
H11A H 0.532067 0.164519 0.388679 0.034 Uiso 1 1 calc R . . . .
H11B H 0.679271 0.069828 0.432299 0.034 Uiso 1 1 calc R . . . .
C12 C 0.6840(3) 0.0703(2) 0.2608(2) 0.0273(6) Uani 1 1 d . . . . .
C13 C 0.6431(4) 0.1364(3) 0.1573(3) 0.0391(7) Uani 1 1 d . . . . .
H13 H 0.595392 0.222022 0.151988 0.047 Uiso 1 1 calc R . . . .
C14 C 0.6706(5) 0.0798(4) 0.0624(3) 0.0550(9) Uani 1 1 d . . . . .
H14 H 0.642841 0.126274 -0.008162 0.066 Uiso 1 1 calc R . . . .
C15 C 0.7384(6) -0.0440(4) 0.0700(3) 0.0668(12) Uani 1 1 d . . . . .
H15 H 0.756828 -0.083405 0.004776 0.080 Uiso 1 1 calc R . . . .
C16 C 0.7795(6) -0.1110(4) 0.1712(4) 0.0664(12) Uani 1 1 d . . . . .
H16 H 0.826199 -0.196798 0.176028 0.080 Uiso 1 1 calc R . . . .
C17 C 0.7531(4) -0.0536(3) 0.2675(3) 0.0433(8) Uani 1 1 d . . . . .
H17 H 0.782725 -0.100043 0.337357 0.052 Uiso 1 1 calc R . . . .
C18 C 0.9819(3) 0.3678(2) 0.4087(2) 0.0241(5) Uani 1 1 d . . . . .
H18A H 0.963677 0.458198 0.409800 0.029 Uiso 1 1 calc R . . . .
H18B H 0.901395 0.329424 0.476845 0.029 Uiso 1 1 calc R . . . .
C19 C 1.1502(3) 0.3119(2) 0.4254(2) 0.0269(5) Uani 1 1 d . . . . .
H19 H 1.235021 0.349770 0.358816 0.032 Uiso 1 1 calc R . . . .
C20 C 1.0687(3) 0.4033(2) 0.1846(2) 0.0218(5) Uani 1 1 d . . . . .
C21 C 1.2077(3) 0.3263(3) 0.1344(2) 0.0292(6) Uani 1 1 d . . . . .
H21 H 1.227343 0.240205 0.168600 0.035 Uiso 1 1 calc R . . . .
C22 C 1.3178(3) 0.3761(3) 0.0336(2) 0.0361(7) Uani 1 1 d . . . . .
H22 H 1.412223 0.323452 -0.001001 0.043 Uiso 1 1 calc R . . . .
C23 C 1.2909(3) 0.5015(3) -0.0164(2) 0.0346(6) Uani 1 1 d . . . . .
H23 H 1.367048 0.534762 -0.084704 0.042 Uiso 1 1 calc R . . . .
C24 C 1.1537(3) 0.5780(3) 0.0329(2) 0.0322(6) Uani 1 1 d . . . . .
H24 H 1.134781 0.664096 -0.001604 0.039 Uiso 1 1 calc R . . . .
C25 C 1.0428(3) 0.5292(2) 0.1334(2) 0.0260(5) Uani 1 1 d . . . . .
H25 H 0.948506 0.582438 0.167302 0.031 Uiso 1 1 calc R . . . .
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'
F F 0.0171 0.0103 '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'
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
C1 O1 C3 110.31(18) . . ?
C1 N1 C2 111.1(2) . . ?
C1 N1 C11 124.2(2) . . ?
C2 N1 C11 122.2(2) . . ?
C1 N2 C4 120.0(2) . . ?
O1 C1 N1 109.86(19) . . ?
N2 C1 O1 124.6(2) . . ?
N2 C1 N1 125.6(2) . . ?
N1 C2 H2A 111.5 . . ?
N1 C2 H2B 111.5 . . ?
N1 C2 C3 101.57(19) . . ?
H2A C2 H2B 109.3 . . ?
C3 C2 H2A 111.5 . . ?
C3 C2 H2B 111.5 . . ?
O1 C3 C2 102.77(18) . . ?
O1 C3 C18 104.36(18) . . ?
O1 C3 C20 106.73(18) . . ?
C18 C3 C2 113.5(2) . . ?
C20 C3 C2 115.0(2) . . ?
C20 C3 C18 113.0(2) . . ?
C5 C4 N2 124.8(2) . . ?
C5 C4 C9 118.1(2) . . ?
C9 C4 N2 116.9(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.7(2) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 119.5 . . ?
C5 C6 C7 121.0(2) . . ?
C7 C6 H6 119.5 . . ?
C6 C7 C10 120.2(3) . . ?
C8 C7 C6 119.0(2) . . ?
C8 C7 C10 120.8(2) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.3(2) . . ?
C9 C8 H8 119.9 . . ?
C4 C9 H9 119.5 . . ?
C8 C9 C4 121.0(2) . . ?
C8 C9 H9 119.5 . . ?
F1 C10 F2 103.7(3) . . ?
F1 C10 F3 107.0(3) . . ?
F1 C10 C7 114.0(3) . . ?
F2 C10 C7 112.8(2) . . ?
F3 C10 F2 104.1(3) . . ?
F3 C10 C7 114.3(3) . . ?
N1 C11 H11A 108.9 . . ?
N1 C11 H11B 108.9 . . ?
N1 C11 C12 113.2(2) . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C13 C12 C11 120.5(2) . . ?
C17 C12 C11 120.5(2) . . ?
C17 C12 C13 119.0(3) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 121.0(3) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.7(3) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.3(3) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.2(3) . . ?
C17 C16 H16 119.9 . . ?
C12 C17 C16 119.8(3) . . ?
C12 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C3 C18 H18A 108.3 . . ?
C3 C18 H18B 108.3 . . ?
H18A C18 H18B 107.4 . . ?
C19 C18 C3 115.7(2) . . ?
C19 C18 H18A 108.3 . . ?
C19 C18 H18B 108.3 . . ?
F4 C19 C18 108.1(2) . . ?
F4 C19 H19 110.7 . . ?
F5 C19 F4 105.3(2) . . ?
F5 C19 C18 111.3(2) . . ?
F5 C19 H19 110.7 . . ?
C18 C19 H19 110.7 . . ?
C21 C20 C3 120.9(2) . . ?
C25 C20 C3 120.0(2) . . ?
C25 C20 C21 119.2(2) . . ?
C20 C21 H21 120.1 . . ?
C20 C21 C22 119.7(3) . . ?
C22 C21 H21 120.1 . . ?
C21 C22 H22 119.7 . . ?
C23 C22 C21 120.6(3) . . ?
C23 C22 H22 119.7 . . ?
C22 C23 H23 120.0 . . ?
C24 C23 C22 120.0(3) . . ?
C24 C23 H23 120.0 . . ?
C23 C24 H24 120.0 . . ?
C23 C24 C25 119.9(3) . . ?
C25 C24 H24 120.0 . . ?
C20 C25 H25 119.7 . . ?
C24 C25 C20 120.7(2) . . ?
C24 C25 H25 119.7 . . ?
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
F1 C10 1.303(4) . ?
F2 C10 1.324(3) . ?
F3 C10 1.308(4) . ?
F4 C19 1.375(3) . ?
F5 C19 1.365(3) . ?
O1 C1 1.349(3) . ?
O1 C3 1.466(3) . ?
N1 C1 1.354(3) . ?
N1 C2 1.450(3) . ?
N1 C11 1.457(3) . ?
N2 C1 1.281(3) . ?
N2 C4 1.408(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.544(3) . ?
C3 C18 1.537(3) . ?
C3 C20 1.514(3) . ?
C4 C5 1.398(4) . ?
C4 C9 1.401(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.375(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.391(4) . ?
C7 C8 1.390(4) . ?
C7 C10 1.481(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.380(4) . ?
C9 H9 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.510(4) . ?
C12 C13 1.387(4) . ?
C12 C17 1.376(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.376(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.371(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.368(6) . ?
C16 H16 0.9500 . ?
C16 C17 1.397(5) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.509(3) . ?
C19 H19 1.0000 . ?
C20 C21 1.393(3) . ?
C20 C25 1.391(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.393(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.382(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.377(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.391(4) . ?
C25 H25 0.9500 . ?
