#------------------------------------------------------------------------------
#$Date: 2019-11-28 19:08:28 +0200 (Thu, 28 Nov 2019) $
#$Revision: 244381 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/63/1556367.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_1556367
loop_
_publ_author_name
'Feng, Chao'
'Loh, Teck-Peng'
_publ_section_title
;
 Copper-catalyzed olefinic trifluoromethylation of enamides at room
 temperature
;
_journal_issue                   12
_journal_name_full               'Chemical Science'
_journal_page_first              3458
_journal_paper_doi               10.1039/c2sc21164e
_journal_volume                  3
_journal_year                    2012
_chemical_formula_moiety         'C12 H9 F3 N2 O'
_chemical_formula_sum            'C12 H9 F3 N2 O'
_chemical_formula_weight         254.21
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 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                 95.4600(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.2648(2)
_cell_length_b                   8.9839(3)
_cell_length_c                   20.5622(5)
_cell_measurement_reflns_used    3207
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      29.61
_cell_measurement_theta_min      3.02
_cell_volume                     1152.04(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0346
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            9979
_diffrn_reflns_theta_full        29.64
_diffrn_reflns_theta_max         29.64
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  0.9873
_exptl_absorpt_correction_T_min  0.9504
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.107
_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     164
_refine_ls_number_reflns         3206
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0454
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0772P)²+0.3540P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1258
_refine_ls_wR_factor_ref         0.1427
_reflns_number_gt                2565
_reflns_number_total             3206
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2sc21164e.txt
_cod_data_source_block           ltp230s
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1556367
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
C1 C 0.2335(2) 0.39184(18) 0.50488(7) 0.0204(3) Uani 1 1 d .
C2 C 0.1971(2) 0.26999(17) 0.45906(7) 0.0170(3) Uani 1 1 d .
C3 C 0.3519(2) 0.23627(18) 0.41714(7) 0.0183(3) Uani 1 1 d .
H3 H 0.4829 0.2902 0.4194 0.022 Uiso 1 1 calc R
C4 C 0.3119(2) 0.12253(17) 0.37190(7) 0.0160(3) Uani 1 1 d .
H4 H 0.4169 0.0979 0.3432 0.019 Uiso 1 1 calc R
C5 C 0.1197(2) 0.04446(16) 0.36818(6) 0.0129(3) Uani 1 1 d .
C6 C -0.0345(2) 0.07951(17) 0.41052(6) 0.0156(3) Uani 1 1 d .
H6 H -0.1663 0.0266 0.4078 0.019 Uiso 1 1 calc R
C7 C 0.0046(2) 0.19126(17) 0.45643(7) 0.0174(3) Uani 1 1 d .
H7 H -0.0987 0.2141 0.4859 0.021 Uiso 1 1 calc R
C8 C 0.0742(2) -0.07143(16) 0.31670(6) 0.0130(3) Uani 1 1 d .
C9 C -0.2167(2) -0.12712(16) 0.22932(6) 0.0141(3) Uani 1 1 d .
C10 C -0.4101(2) -0.05861(18) 0.19257(7) 0.0202(3) Uani 1 1 d .
H10A H -0.4505 -0.1166 0.1529 0.030 Uiso 1 1 calc R
H10B H -0.3771 0.0438 0.1805 0.030 Uiso 1 1 calc R
H10C H -0.5292 -0.0582 0.2202 0.030 Uiso 1 1 calc R
C11 C 0.1903(2) -0.19499(17) 0.31136(7) 0.0162(3) Uani 1 1 d .
H11 H 0.1581 -0.2544 0.2735 0.019 Uiso 1 1 calc R
C12 C 0.3654(2) -0.24708(17) 0.35966(7) 0.0177(3) Uani 1 1 d .
F1 F 0.34693(16) -0.20723(13) 0.42141(4) 0.0292(3) Uani 1 1 d .
F2 F 0.56102(16) -0.19954(15) 0.34693(5) 0.0346(3) Uani 1 1 d .
F3 F 0.37573(19) -0.39568(12) 0.35864(6) 0.0387(3) Uani 1 1 d .
N1 N 0.2606(2) 0.48905(18) 0.54043(7) 0.0274(3) Uani 1 1 d .
N2 N -0.10356(19) -0.03474(13) 0.27300(5) 0.0139(3) Uani 1 1 d .
H2 H -0.1475 0.0582 0.2737 0.017 Uiso 1 1 calc R
O1 O -0.16531(17) -0.25693(12) 0.22118(5) 0.0172(2) 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
N1 C1 C2 179.10(18)
C3 C2 C7 121.12(13)
C3 C2 C1 119.49(14)
C7 C2 C1 119.36(13)
C4 C3 C2 118.92(14)
C4 C3 H3 120.5
C2 C3 H3 120.5
C3 C4 C5 120.56(13)
C3 C4 H4 119.7
C5 C4 H4 119.7
C4 C5 C6 119.94(13)
C4 C5 C8 119.80(12)
C6 C5 C8 120.18(12)
C7 C6 C5 120.06(13)
C7 C6 H6 120.0
C5 C6 H6 120.0
C6 C7 C2 119.38(13)
C6 C7 H7 120.3
C2 C7 H7 120.3
C11 C8 N2 123.20(13)
C11 C8 C5 124.64(12)
N2 C8 C5 112.14(12)
O1 C9 N2 122.68(13)
O1 C9 C10 122.17(13)
N2 C9 C10 115.15(13)
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C8 C11 C12 125.46(13)
C8 C11 H11 117.3
C12 C11 H11 117.3
F1 C12 F3 106.95(13)
F1 C12 F2 105.23(12)
F3 C12 F2 105.50(13)
F1 C12 C11 115.27(12)
F3 C12 C11 109.77(12)
F2 C12 C11 113.46(12)
C9 N2 C8 127.41(13)
C9 N2 H2 116.3
C8 N2 H2 116.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.141(2)
C1 C2 1.448(2)
C2 C3 1.391(2)
C2 C7 1.395(2)
C3 C4 1.388(2)
C3 H3 0.9500
C4 C5 1.390(2)
C4 H4 0.9500
C5 C6 1.3962(19)
C5 C8 1.4927(18)
C6 C7 1.384(2)
C6 H6 0.9500
C7 H7 0.9500
C8 C11 1.338(2)
C8 N2 1.4020(17)
C9 O1 1.2255(18)
C9 N2 1.3699(18)
C9 C10 1.498(2)
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C11 C12 1.483(2)
C11 H11 0.9500
C12 F1 1.3348(17)
C12 F3 1.3368(18)
C12 F2 1.3469(18)
N2 H2 0.8800
