#------------------------------------------------------------------------------
#$Date: 2016-02-18 16:37:37 +0100 (jue 18 de feb de 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/39/1513950.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_1513950
loop_
_publ_author_name
'Wang, Shuai'
'Nie, Jing'
'Zheng, Yan'
'Ma, Jun-An'
_publ_section_title
;
 A direct copper-promoted three-component entry to
 trifluoromethylketoximes.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1606
_journal_page_last               1609
_journal_paper_doi               10.1021/ol500203m
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C11 H9 F3 N2 O'
_chemical_formula_weight         242.20
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.577(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.8552(8)
_cell_length_b                   5.5784(6)
_cell_length_c                   24.405(3)
_cell_measurement_reflns_used    1027
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.96
_cell_measurement_theta_min      3.18
_cell_volume                     1067.3(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            5912
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.67
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_T_max  0.9736
_exptl_absorpt_correction_T_min  0.9634
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         1886
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0469
_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)+(0.0580P)²+0.3628P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1403
_reflns_number_gt                1233
_reflns_number_total             1886
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol500203m_si_002.cif
_cod_data_source_block           n140115d
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN'
changed to 'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'NONE' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        1067.32(19)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1513950
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
F1 F 0.5748(2) -0.0086(4) 0.43034(9) 0.0888(7) Uani 1 1 d .
F2 F 0.6051(2) -0.3152(4) 0.37946(9) 0.0878(7) Uani 1 1 d .
F3 F 0.6131(3) -0.3528(5) 0.46664(10) 0.1135(10) Uani 1 1 d .
O1 O 1.1012(3) -0.2867(4) 0.46878(9) 0.0627(6) Uani 1 1 d .
H1 H 1.1417 -0.3858 0.4907 0.094 Uiso 1 1 calc R
N1 N 1.1071(3) 0.2920(4) 0.36875(9) 0.0465(6) Uani 1 1 d .
N2 N 0.9260(3) -0.3139(4) 0.46319(9) 0.0522(6) Uani 1 1 d .
C1 C 0.9631(3) 0.3180(4) 0.33409(10) 0.0422(7) Uani 1 1 d .
C2 C 0.9341(4) 0.4774(5) 0.29100(12) 0.0543(8) Uani 1 1 d .
H2 H 1.0158 0.5903 0.2827 0.065 Uiso 1 1 calc R
C3 C 0.7810(4) 0.4631(6) 0.26100(13) 0.0630(9) Uani 1 1 d .
H3 H 0.7576 0.5681 0.2319 0.076 Uiso 1 1 calc R
C4 C 0.6606(4) 0.2927(5) 0.27381(13) 0.0587(8) Uani 1 1 d .
H4 H 0.5582 0.2844 0.2526 0.070 Uiso 1 1 calc R
C5 C 0.6885(4) 0.1372(5) 0.31669(11) 0.0493(7) Uani 1 1 d .
H5 H 0.6056 0.0253 0.3245 0.059 Uiso 1 1 calc R
C6 C 0.8417(3) 0.1471(5) 0.34874(10) 0.0406(6) Uani 1 1 d .
C7 C 0.9203(3) 0.0172(5) 0.39526(10) 0.0412(7) Uani 1 1 d .
C8 C 1.0812(3) 0.1129(5) 0.40431(11) 0.0472(7) Uani 1 1 d .
H8 H 1.1614 0.0607 0.4314 0.057 Uiso 1 1 calc R
C9 C 1.2627(4) 0.4335(6) 0.36685(13) 0.0630(9) Uani 1 1 d .
H9A H 1.3432 0.3830 0.3958 0.095 Uiso 1 1 calc R
H9B H 1.2364 0.6000 0.3715 0.095 Uiso 1 1 calc R
H9C H 1.3109 0.4105 0.3320 0.095 Uiso 1 1 calc R
C10 C 0.8503(4) -0.1702(5) 0.42879(11) 0.0461(7) Uani 1 1 d .
C11 C 0.6615(4) -0.2117(7) 0.42671(14) 0.0675(10) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0598(12) 0.1104(17) 0.0988(16) 0.0194(13) 0.0252(11) 0.0146(12)
F2 0.0704(13) 0.0887(15) 0.1013(16) 0.0097(12) -0.0186(11) -0.0349(11)
F3 0.0723(14) 0.152(2) 0.1167(18) 0.0791(17) 0.0140(12) -0.0252(14)
O1 0.0562(13) 0.0723(15) 0.0585(14) 0.0158(11) -0.0035(10) 0.0017(11)
N1 0.0408(13) 0.0476(14) 0.0515(14) -0.0031(11) 0.0059(10) -0.0119(11)
N2 0.0550(15) 0.0563(15) 0.0456(14) 0.0053(12) 0.0038(11) -0.0045(13)
C1 0.0445(16) 0.0400(15) 0.0427(15) -0.0033(12) 0.0085(12) -0.0015(13)
C2 0.0568(18) 0.0466(17) 0.0613(19) 0.0072(14) 0.0190(15) -0.0001(15)
C3 0.063(2) 0.066(2) 0.061(2) 0.0230(16) 0.0106(16) 0.0125(17)
C4 0.0512(18) 0.066(2) 0.0581(19) 0.0108(16) -0.0011(14) 0.0068(16)
C5 0.0452(16) 0.0537(17) 0.0488(17) 0.0057(14) 0.0001(13) -0.0031(14)
C6 0.0423(15) 0.0405(15) 0.0394(14) -0.0018(11) 0.0060(12) -0.0021(12)
C7 0.0436(15) 0.0430(15) 0.0371(14) -0.0024(11) 0.0032(12) -0.0035(13)
C8 0.0455(16) 0.0529(17) 0.0428(15) -0.0031(14) -0.0006(12) -0.0020(14)
C9 0.0497(18) 0.068(2) 0.073(2) -0.0087(17) 0.0140(15) -0.0221(16)
C10 0.0493(16) 0.0491(17) 0.0400(15) 0.0015(13) 0.0030(12) -0.0067(14)
C11 0.056(2) 0.080(2) 0.067(2) 0.0282(19) 0.0046(17) -0.0131(19)
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
N2 O1 H1 109.5
C8 N1 C1 108.8(2)
C8 N1 C9 125.6(2)
C1 N1 C9 125.6(2)
C10 N2 O1 114.5(2)
N1 C1 C2 128.6(3)
N1 C1 C6 108.4(2)
C2 C1 C6 123.0(3)
C3 C2 C1 117.7(3)
C3 C2 H2 121.1
C1 C2 H2 121.1
C2 C3 C4 120.4(3)
C2 C3 H3 119.8
C4 C3 H3 119.8
C5 C4 C3 121.8(3)
C5 C4 H4 119.1
C3 C4 H4 119.1
C4 C5 C6 119.7(3)
C4 C5 H5 120.1
C6 C5 H5 120.1
C5 C6 C1 117.2(2)
C5 C6 C7 136.8(2)
C1 C6 C7 106.0(2)
C8 C7 C6 105.8(2)
C8 C7 C10 124.3(3)
C6 C7 C10 129.9(2)
N1 C8 C7 111.0(2)
N1 C8 H8 124.5
C7 C8 H8 124.5
N1 C9 H9A 109.5
N1 C9 H9B 109.5
H9A C9 H9B 109.5
N1 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
N2 C10 C7 129.9(3)
N2 C10 C11 110.1(2)
C7 C10 C11 120.0(3)
F3 C11 F1 106.6(3)
F3 C11 F2 106.4(3)
F1 C11 F2 106.3(3)
F3 C11 C10 113.3(3)
F1 C11 C10 112.1(3)
F2 C11 C10 111.7(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C11 1.328(4)
F2 C11 1.340(4)
F3 C11 1.327(3)
O1 N2 1.383(3)
O1 H1 0.8200
N1 C8 1.348(3)
N1 C1 1.377(3)
N1 C9 1.458(3)
N2 C10 1.280(4)
C1 C2 1.385(4)
C1 C6 1.410(4)
C2 C3 1.371(4)
C2 H2 0.9300
C3 C4 1.390(4)
C3 H3 0.9300
C4 C5 1.366(4)
C4 H4 0.9300
C5 C6 1.396(4)
C5 H5 0.9300
C6 C7 1.452(4)
C7 C8 1.378(4)
C7 C10 1.456(4)
C8 H8 0.9300
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C10 C11 1.498(4)
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
C8 N1 C1 C2 -179.1(3)
C9 N1 C1 C2 0.3(4)
C8 N1 C1 C6 0.0(3)
C9 N1 C1 C6 179.4(2)
N1 C1 C2 C3 177.8(3)
C6 C1 C2 C3 -1.2(4)
C1 C2 C3 C4 -0.2(4)
C2 C3 C4 C5 1.0(5)
C3 C4 C5 C6 -0.3(4)
C4 C5 C6 C1 -1.1(4)
C4 C5 C6 C7 -178.5(3)
N1 C1 C6 C5 -177.2(2)
C2 C1 C6 C5 1.9(4)
N1 C1 C6 C7 0.8(3)
C2 C1 C6 C7 -180.0(2)
C5 C6 C7 C8 176.2(3)
C1 C6 C7 C8 -1.4(3)
C5 C6 C7 C10 -6.1(5)
C1 C6 C7 C10 176.4(2)
C1 N1 C8 C7 -0.9(3)
C9 N1 C8 C7 179.7(2)
C6 C7 C8 N1 1.4(3)
C10 C7 C8 N1 -176.5(2)
O1 N2 C10 C7 -0.5(4)
O1 N2 C10 C11 -179.0(2)
C8 C7 C10 N2 -16.4(5)
C6 C7 C10 N2 166.1(3)
C8 C7 C10 C11 161.9(3)
C6 C7 C10 C11 -15.5(4)
N2 C10 C11 F3 11.2(4)
C7 C10 C11 F3 -167.5(3)
N2 C10 C11 F1 131.9(3)
C7 C10 C11 F1 -46.8(4)
N2 C10 C11 F2 -108.9(3)
C7 C10 C11 F2 72.5(4)
