#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/11/73/4117358.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_4117358
loop_
_publ_author_name
'Yuta Fujiwara'
'Janice A. Dixon'
'Rodrigo A. Rodriguez'
'Ryan D. Baxter'
'Darryl D. Dixon'
'Michael R. Collins'
'Donna G. Blackmond'
'Phil S. Baran'
_publ_section_title
;
 A New Reagent for Direct Difluoromethylation
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1494
_journal_page_last               1497
_journal_paper_doi               10.1021/ja211422g
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C7 H4 F2 N2'
_chemical_formula_weight         154.12
_chemical_name_systematic
; 
 ? 
;
_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_method           SHELXL-97
_cell_angle_alpha                103.999(2)
_cell_angle_beta                 97.334(2)
_cell_angle_gamma                91.227(2)
_cell_formula_units_Z            2
_cell_length_a                   4.0541(8)
_cell_length_b                   6.6842(13)
_cell_length_c                   13.040(3)
_cell_measurement_reflns_used    1541
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.86
_cell_measurement_theta_min      3.15
_cell_volume                     339.56(12)
_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, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_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  0.0225
_diffrn_reflns_av_sigmaI/netI    0.0328
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3059
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.89
_diffrn_reflns_theta_min         1.62
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  0.943
_exptl_absorpt_correction_T_min  0.890
_exptl_absorpt_correction_type   multiu-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_description       needle
_exptl_crystal_F_000             156
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1292
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0409
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0690P)²+0.0401P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1142
_refine_ls_wR_factor_ref         0.1230
_reflns_number_gt                1035
_reflns_number_total             1292
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja211422g_si_003.cif
_cod_data_source_block           baran244
_cod_original_cell_volume        339.56(11)
_cod_database_code               4117358
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
F1 F 0.2226(3) 0.12394(16) 0.94927(8) 0.0397(3) Uani 1 1 d .
F2 F 0.5331(3) 0.02051(15) 0.82302(8) 0.0418(3) Uani 1 1 d .
N1 N -0.3083(5) 0.2278(3) 0.45851(14) 0.0555(5) Uani 1 1 d .
N2 N 0.1713(4) 0.5079(2) 0.87506(11) 0.0318(4) Uani 1 1 d .
C1 C -0.2029(5) 0.2870(3) 0.54685(15) 0.0409(5) Uani 1 1 d .
C2 C -0.0719(4) 0.3633(3) 0.65926(14) 0.0321(4) Uani 1 1 d .
C3 C 0.1128(4) 0.2359(2) 0.71300(14) 0.0314(4) Uani 1 1 d .
H3 H 0.1577 0.0996 0.6774 0.038 Uiso 1 1 calc R
C4 C 0.2277(4) 0.3169(2) 0.82045(13) 0.0283(4) Uani 1 1 d .
C5 C 0.4260(4) 0.1938(3) 0.88755(14) 0.0312(4) Uani 1 1 d .
H5 H 0.6195 0.2802 0.9334 0.037 Uiso 1 1 calc R
C6 C -0.0085(5) 0.6260(3) 0.82124(15) 0.0346(4) Uani 1 1 d .
H6 H -0.0511 0.7613 0.8589 0.042 Uiso 1 1 calc R
C7 C -0.1350(4) 0.5618(3) 0.71400(15) 0.0339(4) Uani 1 1 d .
H7 H -0.2606 0.6504 0.6790 0.041 Uiso 1 1 calc R
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 0.0402(6) 0.0463(6) 0.0366(6) 0.0182(5) 0.0041(5) 0.0068(5)
F2 0.0477(7) 0.0372(6) 0.0377(7) 0.0054(5) 0.0006(5) 0.0176(5)
N1 0.0737(13) 0.0526(11) 0.0340(10) 0.0056(8) -0.0086(9) 0.0177(9)
N2 0.0322(8) 0.0297(7) 0.0309(8) 0.0046(6) 0.0001(6) 0.0037(6)
C1 0.0491(12) 0.0389(10) 0.0333(11) 0.0082(8) 0.0005(9) 0.0116(8)
C2 0.0338(10) 0.0358(9) 0.0259(9) 0.0072(7) 0.0022(7) 0.0032(7)
C3 0.0330(10) 0.0297(9) 0.0291(9) 0.0032(7) 0.0032(7) 0.0036(7)
C4 0.0251(9) 0.0294(8) 0.0293(9) 0.0056(7) 0.0024(7) 0.0022(6)
C5 0.0303(9) 0.0311(8) 0.0303(9) 0.0050(7) 0.0019(7) 0.0040(7)
C6 0.0376(10) 0.0293(9) 0.0361(10) 0.0074(7) 0.0029(7) 0.0058(7)
C7 0.0343(9) 0.0342(9) 0.0337(10) 0.0117(7) 0.0000(7) 0.0059(7)
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'
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
C4 N2 C6 117.18(15)
N1 C1 C2 179.4(2)
C7 C2 C3 119.87(16)
C7 C2 C1 120.10(16)
C3 C2 C1 120.02(15)
C4 C3 C2 117.26(15)
N2 C4 C3 124.08(16)
N2 C4 C5 113.61(15)
C3 C4 C5 122.31(15)
F1 C5 F2 105.83(12)
F1 C5 C4 109.39(13)
F2 C5 C4 109.99(14)
N2 C6 C7 123.80(16)
C6 C7 C2 117.81(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C5 1.371(2)
F2 C5 1.3718(19)
N1 C1 1.146(3)
N2 C4 1.343(2)
N2 C6 1.345(2)
C1 C2 1.456(2)
C2 C7 1.392(2)
C2 C3 1.400(2)
C3 C4 1.389(2)
C4 C5 1.512(2)
C6 C7 1.386(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 28604925
