#------------------------------------------------------------------------------
#$Date: 2015-11-18 09:37:16 +0200 (Wed, 18 Nov 2015) $
#$Revision: 170397 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/33/7223303.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_7223303
loop_
_publ_author_name
'Tian, Lei'
'Cui, Can'
'Zhu, Cong'
'Yang, Hui-Hui'
'Li, Jian-Qiang'
'Zhao, Wei-Guang'
_publ_section_title
;
 Novel exocyclic enamides: synthesis and evaluation of the fungicidal
 activities of 5-methylene-2-(trifluoromethyl)morpholin-3-one derivatives
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA20138A
_journal_year                    2015
_chemical_formula_sum            'C18 H13 F4 N O2'
_chemical_formula_weight         351.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-11-11 deposited with the CCDC.
2015-11-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.33(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.352(3)
_cell_length_b                   9.5750(19)
_cell_length_c                   13.866(3)
_cell_measurement_reflns_used    5299
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      1.7
_cell_volume                     1573.8(6)
_computing_cell_refinement
; 
Rigaku CrystalClear-SM Expert 2.0 r4 
;
_computing_data_collection
; 
Rigaku CrystalClear-SM Expert 2.0 r4 
;
_computing_data_reduction
; 
Rigaku CrystalClear-SM Expert 2.0 r4 
;
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 14.2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type
; 
Rigaku Saturn 724 CCD 
;
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_laue_measured_fraction_full 1.000
_diffrn_reflns_laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18292
_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         27.950
_diffrn_reflns_theta_min         1.718
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.816
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   CrystalClear
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_description       Prism
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3755
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0361
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0539P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.0968
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2913
_reflns_number_total             3755
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5ra20138a2.cif
_cod_data_source_block           sa
_cod_database_code               7223303
_shelx_shelxl_version_number     2014/7
_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_min   0.970
_shelx_estimated_absorpt_t_max   0.977
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
F1 F 0.44397(6) 0.43005(8) 0.40349(5) 0.0321(2) Uani 1 1 d . .
F2 F 0.37443(6) 0.35840(8) 0.52088(5) 0.02750(18) Uani 1 1 d . .
F3 F 0.29499(6) 0.52866(7) 0.42415(5) 0.02938(19) Uani 1 1 d . .
F4 F -0.34413(6) 0.30730(8) 0.38439(6) 0.03053(19) Uani 1 1 d . .
O1 O 0.26546(7) 0.36803(8) 0.25676(6) 0.02040(19) Uani 1 1 d . .
O2 O 0.15070(7) 0.28213(10) 0.45700(6) 0.0254(2) Uani 1 1 d . .
N1 N 0.06332(8) 0.30751(10) 0.29042(7) 0.0184(2) Uani 1 1 d . .
C1 C 0.34769(10) 0.40514(13) 0.42631(9) 0.0220(3) Uani 1 1 d . .
C2 C 0.27335(9) 0.30213(12) 0.35047(8) 0.0178(2) Uani 1 1 d . .
C3 C 0.15726(10) 0.29552(12) 0.37121(8) 0.0182(2) Uani 1 1 d . .
C4 C 0.06689(10) 0.31787(12) 0.18866(9) 0.0206(3) Uani 1 1 d . .
C5 C 0.18276(10) 0.30026(13) 0.17652(8) 0.0225(3) Uani 1 1 d . .
H5A H 0.2007 0.1995 0.1761 0.027 Uiso 1 1 calc R U
H5B H 0.1852 0.3406 0.1114 0.027 Uiso 1 1 calc R U
C6 C -0.02418(11) 0.33787(15) 0.11159(10) 0.0310(3) Uani 1 1 d . .
H6A H -0.0963 0.3460 0.1229 0.037 Uiso 1 1 calc R U
H6B H -0.0171 0.3440 0.0452 0.037 Uiso 1 1 calc R U
C7 C 0.33006(9) 0.15796(12) 0.35849(9) 0.0195(2) Uani 1 1 d . .
C8 C 0.41199(10) 0.13621(14) 0.30836(10) 0.0268(3) Uani 1 1 d . .
H8 H 0.4315 0.2099 0.2705 0.032 Uiso 1 1 calc R U
C9 C 0.46506(10) 0.00765(15) 0.31344(10) 0.0326(3) Uani 1 1 d . .
H9 H 0.5205 -0.0065 0.2788 0.039 Uiso 1 1 calc R U
C10 C 0.43753(11) -0.10019(14) 0.36891(10) 0.0332(3) Uani 1 1 d . .
H10 H 0.4739 -0.1882 0.3722 0.040 Uiso 1 1 calc R U
C11 C 0.35746(11) -0.07950(14) 0.41923(10) 0.0316(3) Uani 1 1 d . .
H11 H 0.3390 -0.1534 0.4575 0.038 Uiso 1 1 calc R U
C12 C 0.30328(10) 0.04910(13) 0.41449(9) 0.0251(3) Uani 1 1 d . .
H12 H 0.2481 0.0626 0.4494 0.030 Uiso 1 1 calc R U
C13 C -0.04474(9) 0.30864(12) 0.31335(8) 0.0186(2) Uani 1 1 d . .
C14 C -0.11593(10) 0.19445(12) 0.28783(9) 0.0235(3) Uani 1 1 d . .
H14 H -0.0949 0.1167 0.2545 0.028 Uiso 1 1 calc R U
C15 C -0.21817(10) 0.19419(13) 0.31122(10) 0.0256(3) Uani 1 1 d . .
H15 H -0.2687 0.1175 0.2933 0.031 Uiso 1 1 calc R U
C16 C -0.24424(10) 0.30777(13) 0.36090(9) 0.0216(3) Uani 1 1 d . .
C17 C -0.17453(10) 0.42183(12) 0.38844(9) 0.0220(3) Uani 1 1 d . .
H17 H -0.1951 0.4979 0.4236 0.026 Uiso 1 1 calc R U
C18 C -0.07294(10) 0.42252(12) 0.36320(9) 0.0206(2) Uani 1 1 d . .
H18 H -0.0235 0.5003 0.3800 0.025 Uiso 1 1 calc R U
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
C2 O1 C5 110.99(9)
C3 N1 C4 123.96(10)
C3 N1 C13 116.03(9)
C4 N1 C13 120.01(10)
F1 C1 F2 107.55(10)
F1 C1 F3 107.17(10)
F2 C1 F3 107.49(9)
F1 C1 C2 110.60(9)
F2 C1 C2 112.98(10)
F3 C1 C2 110.80(10)
O1 C2 C7 112.14(9)
O1 C2 C3 111.11(9)
C7 C2 C3 112.24(9)
O1 C2 C1 102.35(9)
C7 C2 C1 110.67(10)
C3 C2 C1 107.81(9)
O2 C3 N1 122.09(10)
O2 C3 C2 120.40(10)
N1 C3 C2 117.50(9)
C6 C4 N1 123.38(11)
C6 C4 C5 123.06(11)
N1 C4 C5 113.55(10)
O1 C5 C4 110.87(9)
O1 C5 H5A 109.5
C4 C5 H5A 109.5
O1 C5 H5B 109.5
C4 C5 H5B 109.5
H5A C5 H5B 108.1
C4 C6 H6A 120.0
C4 C6 H6B 120.0
H6A C6 H6B 120.0
C12 C7 C8 119.01(11)
C12 C7 C2 122.48(10)
C8 C7 C2 118.51(10)
C9 C8 C7 120.38(12)
C9 C8 H8 119.8
C7 C8 H8 119.8
C10 C9 C8 120.21(12)
C10 C9 H9 119.9
C8 C9 H9 119.9
C11 C10 C9 119.86(12)
C11 C10 H10 120.1
C9 C10 H10 120.1
C10 C11 C12 120.49(12)
C10 C11 H11 119.8
C12 C11 H11 119.8
C7 C12 C11 120.05(12)
C7 C12 H12 120.0
C11 C12 H12 120.0
C14 C13 C18 121.16(10)
C14 C13 N1 119.56(10)
C18 C13 N1 119.25(10)
C13 C14 C15 119.68(11)
C13 C14 H14 120.2
C15 C14 H14 120.2
C16 C15 C14 118.19(11)
C16 C15 H15 120.9
C14 C15 H15 120.9
F4 C16 C15 118.25(10)
F4 C16 C17 118.33(10)
C15 C16 C17 123.42(11)
C16 C17 C18 118.10(11)
C16 C17 H17 120.9
C18 C17 H17 120.9
C13 C18 C17 119.42(11)
C13 C18 H18 120.3
C17 C18 H18 120.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C1 1.3353(13)
F2 C1 1.3362(14)
F3 C1 1.3463(14)
F4 C16 1.3617(13)
O1 C2 1.4229(13)
O1 C5 1.4364(15)
O2 C3 1.2216(14)
N1 C3 1.3724(15)
N1 C4 1.4275(15)
N1 C13 1.4565(14)
C1 C2 1.5423(16)
C2 C7 1.5378(16)
C2 C3 1.5410(15)
C4 C6 1.3297(18)
C4 C5 1.4969(16)
C5 H5A 0.9900
C5 H5B 0.9900
C6 H6A 0.9500
C6 H6B 0.9500
C7 C12 1.3939(17)
C7 C8 1.3951(17)
C8 C9 1.3871(18)
C8 H8 0.9500
C9 C10 1.386(2)
C9 H9 0.9500
C10 C11 1.3756(19)
C10 H10 0.9500
C11 C12 1.3942(17)
C11 H11 0.9500
C12 H12 0.9500
C13 C14 1.3853(16)
C13 C18 1.3869(16)
C14 C15 1.3894(16)
C14 H14 0.9500
C15 C16 1.3732(17)
C15 H15 0.9500
C16 C17 1.3766(16)
C17 C18 1.3943(16)
C17 H17 0.9500
C18 H18 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C17 H17 O2 0.95 2.64 3.5157(16) 153.6 3_566
C15 H15 O1 0.95 2.49 3.2670(16) 138.9 2_545
C5 H5B O2 0.99 2.37 3.0605(15) 125.9 4_565
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C5 O1 C2 C7 71.51(11)
C5 O1 C2 C3 -55.01(12)
C5 O1 C2 C1 -169.86(9)
F1 C1 C2 O1 -54.27(12)
F2 C1 C2 O1 -174.89(9)
F3 C1 C2 O1 64.42(11)
F1 C1 C2 C7 65.40(12)
F2 C1 C2 C7 -55.22(12)
F3 C1 C2 C7 -175.91(9)
F1 C1 C2 C3 -171.51(9)
F2 C1 C2 C3 67.87(12)
F3 C1 C2 C3 -52.81(12)
C4 N1 C3 O2 -177.47(11)
C13 N1 C3 O2 2.23(16)
C4 N1 C3 C2 3.60(16)
C13 N1 C3 C2 -176.70(9)
O1 C2 C3 O2 -158.23(10)
C7 C2 C3 O2 75.30(13)
C1 C2 C3 O2 -46.83(14)
O1 C2 C3 N1 20.73(14)
C7 C2 C3 N1 -105.74(11)
C1 C2 C3 N1 132.12(10)
C3 N1 C4 C6 -175.81(12)
C13 N1 C4 C6 4.50(17)
C3 N1 C4 C5 5.72(15)
C13 N1 C4 C5 -173.96(10)
C2 O1 C5 C4 65.76(12)
C6 C4 C5 O1 142.32(12)
N1 C4 C5 O1 -39.21(13)
O1 C2 C7 C12 -149.28(11)
C3 C2 C7 C12 -23.37(15)
C1 C2 C7 C12 97.12(13)
O1 C2 C7 C8 31.26(14)
C3 C2 C7 C8 157.17(10)
C1 C2 C7 C8 -82.34(13)
C12 C7 C8 C9 0.65(18)
C2 C7 C8 C9 -179.87(11)
C7 C8 C9 C10 -0.4(2)
C8 C9 C10 C11 -0.1(2)
C9 C10 C11 C12 0.3(2)
C8 C7 C12 C11 -0.47(18)
C2 C7 C12 C11 -179.93(11)
C10 C11 C12 C7 -0.01(19)
C3 N1 C13 C14 -109.14(12)
C4 N1 C13 C14 70.57(14)
C3 N1 C13 C18 68.90(14)
C4 N1 C13 C18 -111.39(12)
C18 C13 C14 C15 0.86(18)
N1 C13 C14 C15 178.86(10)
C13 C14 C15 C16 -1.07(18)
C14 C15 C16 F4 -179.62(10)
C14 C15 C16 C17 0.18(19)
F4 C16 C17 C18 -179.28(10)
C15 C16 C17 C18 0.92(18)
C14 C13 C18 C17 0.26(17)
N1 C13 C18 C17 -177.75(10)
C16 C17 C18 C13 -1.12(17)
