#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:10:11 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178460 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/81/4028175.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_4028175
loop_
_publ_author_name
'Robert S. Foster'
'Harry Adams'
'Harald Jakobi'
'Joseph P. A. Harrity'
_publ_section_title
;
 Synthesis of 4-Fluoromethylsydnones and their Participation in Alkyne
 Cycloaddition Reactions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4049
_journal_page_last               4064
_journal_paper_doi               10.1021/jo400381a
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C9 H6 F2 N2 O2'
_chemical_formula_weight         212.16
_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                 98.920(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.0878(7)
_cell_length_b                   6.1470(6)
_cell_length_c                   19.9237(19)
_cell_measurement_reflns_used    6067
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.41
_cell_measurement_theta_min      2.91
_cell_volume                     857.55(14)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0687
_diffrn_reflns_av_sigmaI/netI    0.0394
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            12618
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_T_max  0.9656
_exptl_absorpt_correction_T_min  0.9369
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.041(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1944
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0376
_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)+(0.0611P)²+0.1776P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1085
_refine_ls_wR_factor_ref         0.1136
_reflns_number_gt                1666
_reflns_number_total             1944
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400381a_si_002.cif
_cod_data_source_block           ohj240_0m
_cod_database_code               4028175
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
N1 N 0.07618(15) 0.74882(13) 0.10227(5) 0.0142(3) Uani 1 1 d .
N2 N -0.10961(15) 0.76138(14) 0.09149(5) 0.0178(3) Uani 1 1 d .
O1 O -0.00629(14) 0.75088(12) -0.07158(5) 0.0209(3) Uani 1 1 d .
O2 O -0.15867(13) 0.76335(12) 0.02200(5) 0.0186(3) Uani 1 1 d .
F1 F 0.45559(10) 0.56223(12) 0.06966(4) 0.0255(2) Uani 1 1 d .
F2 F 0.45270(10) 0.91553(13) 0.07638(4) 0.0269(2) Uani 1 1 d .
C1 C 0.00733(18) 0.75053(15) -0.00999(6) 0.0159(3) Uani 1 1 d .
C2 C 0.15810(18) 0.74115(16) 0.04526(6) 0.0148(3) Uani 1 1 d .
C3 C 0.16658(17) 0.74272(16) 0.17274(6) 0.0150(3) Uani 1 1 d .
C4 C 0.26069(16) 0.55419(18) 0.19738(6) 0.0170(3) Uani 1 1 d .
H4 H 0.2717 0.4364 0.1689 0.020 Uiso 1 1 calc R
C5 C 0.33815(17) 0.5470(2) 0.26608(6) 0.0190(3) Uani 1 1 d .
H5 H 0.4024 0.4232 0.2841 0.023 Uiso 1 1 calc R
C6 C 0.31926(19) 0.72520(19) 0.30766(7) 0.0201(3) Uani 1 1 d .
H6 H 0.3700 0.7189 0.3535 0.024 Uiso 1 1 calc R
C7 C 0.22564(17) 0.9119(2) 0.28147(6) 0.0207(3) Uani 1 1 d .
H7 H 0.2159 1.0305 0.3097 0.025 Uiso 1 1 calc R
C8 C 0.14617(16) 0.92280(19) 0.21316(6) 0.0179(3) Uani 1 1 d .
H8 H 0.0816 1.0464 0.1952 0.021 Uiso 1 1 calc R
C9 C 0.36412(18) 0.74373(17) 0.04114(7) 0.0174(3) Uani 1 1 d .
H9 H 0.3818 0.7540 -0.0066 0.020(4) 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
N1 0.0139(5) 0.0135(5) 0.0149(6) 0.0009(3) 0.0009(4) -0.0004(3)
N2 0.0153(5) 0.0208(6) 0.0164(6) 0.0027(3) -0.0001(4) 0.0000(3)
O1 0.0278(5) 0.0198(5) 0.0138(5) 0.0005(3) -0.0005(4) -0.0027(3)
O2 0.0164(5) 0.0217(5) 0.0166(5) 0.0026(3) -0.0007(4) -0.0014(3)
F1 0.0214(4) 0.0284(4) 0.0269(4) 0.0046(3) 0.0047(3) 0.0082(3)
F2 0.0201(4) 0.0294(5) 0.0307(5) -0.0078(3) 0.0024(3) -0.0076(3)
C1 0.0197(6) 0.0102(6) 0.0175(7) 0.0010(4) 0.0016(5) -0.0022(4)
C2 0.0178(6) 0.0138(6) 0.0128(6) -0.0001(4) 0.0025(5) -0.0009(4)
C3 0.0130(6) 0.0197(6) 0.0125(6) 0.0009(4) 0.0020(4) -0.0014(4)
C4 0.0181(6) 0.0168(6) 0.0164(6) -0.0004(4) 0.0032(4) 0.0005(4)
C5 0.0182(6) 0.0197(6) 0.0185(6) 0.0038(4) 0.0014(5) 0.0014(4)
C6 0.0183(6) 0.0280(7) 0.0138(6) 0.0001(4) 0.0020(5) -0.0021(5)
C7 0.0200(6) 0.0243(6) 0.0184(6) -0.0053(5) 0.0046(5) 0.0006(5)
C8 0.0160(6) 0.0187(6) 0.0192(6) -0.0004(4) 0.0031(4) 0.0022(4)
C9 0.0175(6) 0.0194(7) 0.0155(6) -0.0007(4) 0.0028(5) 0.0001(4)
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 N1 C2 114.68(10)
N2 N1 C3 116.38(10)
C2 N1 C3 128.93(10)
N1 N2 O2 104.94(10)
N2 O2 C1 110.66(9)
O1 C1 C2 135.99(13)
O1 C1 O2 120.64(12)
C2 C1 O2 103.37(10)
N1 C2 C1 106.35(11)
N1 C2 C9 127.10(11)
C1 C2 C9 126.32(11)
C4 C3 C8 123.20(11)
C4 C3 N1 118.67(9)
C8 C3 N1 118.05(10)
C3 C4 C5 117.91(10)
C3 C4 H4 121.0
C5 C4 H4 121.0
C6 C5 C4 119.97(11)
C6 C5 H5 120.0
C4 C5 H5 120.0
C7 C6 C5 120.80(11)
C7 C6 H6 119.6
C5 C6 H6 119.6
C6 C7 C8 120.35(11)
C6 C7 H7 119.8
C8 C7 H7 119.8
C3 C8 C7 117.76(11)
C3 C8 H8 121.1
C7 C8 H8 121.1
F2 C9 F1 105.45(10)
F2 C9 C2 111.08(9)
F1 C9 C2 112.17(9)
F2 C9 H9 109.4
F1 C9 H9 109.4
C2 C9 H9 109.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 N2 1.3033(15)
N1 C2 1.3542(16)
N1 C3 1.4507(16)
N2 O2 1.3742(14)
O1 C1 1.2158(16)
O2 C1 1.4246(16)
F1 C9 1.3688(13)
F2 C9 1.3660(13)
C1 C2 1.4115(17)
C2 C9 1.4753(17)
C3 C4 1.3882(15)
C3 C8 1.3895(16)
C4 C5 1.3942(15)
C4 H4 0.9300
C5 C6 1.3923(17)
C5 H5 0.9300
C6 C7 1.3866(17)
C6 H6 0.9300
C7 C8 1.3916(16)
C7 H7 0.9300
C8 H8 0.9300
C9 H9 0.9800
