#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/51/4025117.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_4025117
loop_
_publ_author_name
'Matthew R. Smith'
'Alexander J. Blake'
'Christopher J. Hayes'
'Malcolm F. G. Stevens'
'Christopher J. Moody'
_publ_section_title
;
Carbene Reactivity of 4-Diazo-4H-imidazoles toward Nucleophiles and
Aromatic Compounds
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9372
_journal_page_last               9380
_journal_paper_doi               10.1021/jo902165w
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C23 H12 F6 N2 O2'
_chemical_formula_sum            'C23 H12 F6 N2 O2'
_chemical_formula_weight         462.35
_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
_audit_creation_method           'enCIFer editing of SHELXL97 CIF output'
_cell_angle_alpha                114.378(2)
_cell_angle_beta                 93.584(2)
_cell_angle_gamma                97.782(2)
_cell_formula_units_Z            2
_cell_length_a                   8.4982(7)
_cell_length_b                   10.9169(9)
_cell_length_c                   11.4853(10)
_cell_measurement_reflns_used    2936
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.95
_cell_measurement_theta_min      2.15
_cell_volume                     953.3(2)
_computing_cell_refinement       'Bruker SAINT version 6.36A (Bruker, 2000)'
_computing_data_collection       'Bruker SMART version 5.625 (Bruker, 2001)'
_computing_data_reduction        'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)'
_computing_publication_material
'enCIFer(Allen et al.,2004);PLATON(Spek,2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       omega
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.101
_diffrn_reflns_av_sigmaI/netI    0.084
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8488
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.08
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.77
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.38
_refine_diff_density_min         -0.21
_refine_diff_density_rms         0.05
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4290
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.06
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0427
_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)+(0.046P)²+0.135P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.117
_refine_ls_wR_factor_ref         0.121
_reflns_number_gt                3782
_reflns_number_total             4290
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            jo902165w_si_002.cif
_cod_data_source_block           phimac
_cod_database_code               4025117
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.57090(14) 0.63904(10) 0.32243(10) 0.0227(2) Uani 1 1 d . . .
C2 C 0.70495(16) 0.60401(13) 0.36838(12) 0.0228(3) Uani 1 1 d . . .
N3 N 0.66944(14) 0.48346(11) 0.36878(10) 0.0247(2) Uani 1 1 d . . .
C4 C 0.50973(16) 0.43727(13) 0.32222(12) 0.0236(3) Uani 1 1 d . . .
C5 C 0.44417(16) 0.53023(12) 0.29261(12) 0.0226(3) Uani 1 1 d . . .
C6 C 0.86612(16) 0.68810(13) 0.41093(12) 0.0238(3) Uani 1 1 d . . .
C7 C 0.96495(17) 0.66806(13) 0.50088(13) 0.0266(3) Uani 1 1 d . . .
H7 H 0.9254 0.6051 0.5342 0.032 Uiso 1 1 calc R . .
C8 C 1.12033(18) 0.73958(14) 0.54159(13) 0.0299(3) Uani 1 1 d . . .
H8 H 1.1872 0.7254 0.6027 0.036 Uiso 1 1 calc R . .
C9 C 1.17881(18) 0.83159(14) 0.49375(14) 0.0328(3) Uani 1 1 d . . .
H9 H 1.2855 0.8806 0.5220 0.039 Uiso 1 1 calc R . .
C10 C 1.08131(19) 0.85212(16) 0.40439(16) 0.0374(4) Uani 1 1 d . . .
H10 H 1.1211 0.9159 0.3721 0.045 Uiso 1 1 calc R . .
C11 C 0.92589(19) 0.77987(15) 0.36205(15) 0.0338(3) Uani 1 1 d . . .
H11 H 0.8602 0.7930 0.2997 0.041 Uiso 1 1 calc R . .
C12 C 0.43296(17) 0.30251(13) 0.31300(13) 0.0257(3) Uani 1 1 d . . .
O12 O 0.49052(14) 0.24511(11) 0.36954(12) 0.0410(3) Uani 1 1 d . . .
C13 C 0.19421(19) 0.13705(14) 0.23487(14) 0.0324(3) Uani 1 1 d . . .
H13A H 0.0845 0.1562 0.2482 0.039 Uiso 1 1 calc R . .
H13B H 0.2371 0.1200 0.3079 0.039 Uiso 1 1 calc R . .
O13 O 0.29332(13) 0.25580(9) 0.23537(10) 0.0313(2) Uani 1 1 d . . .
C14 C 0.18582(16) 0.01052(13) 0.11165(13) 0.0252(3) Uani 1 1 d . . .
C15 C 0.0684(2) -0.10042(15) 0.09090(15) 0.0367(4) Uani 1 1 d . . .
H15 H -0.0035 -0.0936 0.1525 0.044 Uiso 1 1 calc R . .
C16 C 0.0555(3) -0.22129(16) -0.01945(17) 0.0501(5) Uani 1 1 d . . .
H16 H -0.0241 -0.2973 -0.0324 0.060 Uiso 1 1 calc R . .
C17 C 0.1572(3) -0.23193(16) -0.11026(16) 0.0477(5) Uani 1 1 d . . .
H17 H 0.1482 -0.3151 -0.1855 0.057 Uiso 1 1 calc R . .
C18 C 0.2722(2) -0.12146(18) -0.09163(16) 0.0435(4) Uani 1 1 d . . .
H18 H 0.3416 -0.1279 -0.1549 0.052 Uiso 1 1 calc R . .
C19 C 0.28691(19) -0.00033(15) 0.01987(15) 0.0352(3) Uani 1 1 d . . .
H19 H 0.3671 0.0753 0.0327 0.042 Uiso 1 1 calc R . .
C20 C 0.55752(17) 0.76839(13) 0.33009(13) 0.0253(3) Uani 1 1 d . . .
C21 C 0.50767(18) 0.79522(13) 0.23328(14) 0.0295(3) Uani 1 1 d . . .
C22 C 0.45569(18) 0.69432(15) 0.10097(14) 0.0302(3) Uani 1 1 d . . .
C23 C 0.33272(18) 0.59267(14) 0.06571(13) 0.0289(3) Uani 1 1 d . . .
C24 C 0.23286(17) 0.56212(13) 0.15159(13) 0.0269(3) Uani 1 1 d . . .
C25 C 0.28099(16) 0.53084(12) 0.24690(13) 0.0248(3) Uani 1 1 d . . .
F20 F 0.60018(11) 0.86937(8) 0.44822(8) 0.0321(2) Uani 1 1 d . . .
F21 F 0.50113(13) 0.92515(9) 0.25543(9) 0.0427(3) Uani 1 1 d . . .
F22 F 0.54192(12) 0.71011(10) 0.01230(9) 0.0423(2) Uani 1 1 d . . .
F23 F 0.29212(12) 0.50657(9) -0.05994(8) 0.0382(2) Uani 1 1 d . . .
F24 F 0.07547(10) 0.55875(9) 0.12444(8) 0.0351(2) Uani 1 1 d . . .
F25 F 0.16873(10) 0.49526(8) 0.30937(8) 0.0316(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'
F F 0.0171 0.0103 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C20 126.01(11) . . ?
C2 N1 C5 106.77(10) . . ?
C20 N1 C5 126.00(12) . . ?
N3 C2 N1 110.76(11) . . ?
N3 C2 C6 123.51(12) . . ?
N1 C2 C6 125.72(11) . . ?
C2 N3 C4 106.42(11) . . ?
C5 C4 N3 111.26(11) . . ?
C5 C4 C12 129.61(12) . . ?
N3 C4 C12 119.12(12) . . ?
C4 C5 N1 104.79(11) . . ?
C4 C5 C25 131.69(12) . . ?
N1 C5 C25 123.45(12) . . ?
C11 C6 C7 119.35(13) . . ?
C11 C6 C2 123.67(12) . . ?
C7 C6 C2 116.91(12) . . ?
C8 C7 C6 120.19(13) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 120.31(13) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C10 119.85(13) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C11 C10 C9 120.25(14) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C6 120.05(14) . . ?
C10 C11 H11 120.0 . . ?
C6 C11 H11 120.0 . . ?
O12 C12 O13 125.28(12) . . ?
O12 C12 C4 123.19(13) . . ?
O13 C12 C4 111.53(11) . . ?
O13 C13 C14 113.13(12) . . ?
O13 C13 H13A 109.0 . . ?
C14 C13 H13A 109.0 . . ?
O13 C13 H13B 109.0 . . ?
C14 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C12 O13 C13 116.85(11) . . ?
C19 C14 C15 119.07(13) . . ?
C19 C14 C13 123.83(12) . . ?
C15 C14 C13 117.10(13) . . ?
C16 C15 C14 120.25(16) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C15 120.47(16) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 119.69(15) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C17 C18 C19 120.05(17) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C14 C19 C18 120.45(14) . . ?
C14 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C21 C20 F20 120.20(12) . . ?
C21 C20 N1 125.82(12) . . ?
F20 C20 N1 113.98(11) . . ?
C20 C21 F21 119.09(13) . . ?
C20 C21 C22 125.45(12) . . ?
F21 C21 C22 115.46(12) . . ?
C23 C22 F22 120.24(13) . . ?
C23 C22 C21 124.34(14) . . ?
F22 C22 C21 115.41(12) . . ?
C22 C23 F23 119.67(14) . . ?
C22 C23 C24 125.78(13) . . ?
F23 C23 C24 114.55(12) . . ?
C25 C24 F24 118.80(13) . . ?
C25 C24 C23 126.48(13) . . ?
F24 C24 C23 114.61(12) . . ?
C24 C25 F25 117.72(13) . . ?
C24 C25 C5 127.47(13) . . ?
F25 C25 C5 114.81(11) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.3899(17) . ?
N1 C20 1.3989(17) . ?
N1 C5 1.3999(16) . ?
C2 N3 1.3117(17) . ?
C2 C6 1.4707(18) . ?
N3 C4 1.3724(17) . ?
C4 C5 1.3676(18) . ?
C4 C12 1.4846(18) . ?
C5 C25 1.4536(19) . ?
C6 C11 1.3925(19) . ?
C6 C7 1.3959(19) . ?
C7 C8 1.384(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.383(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.387(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.387(2) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 O12 1.1970(17) . ?
C12 O13 1.3386(17) . ?
C13 O13 1.4449(16) . ?
C13 C14 1.5043(18) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C19 1.379(2) . ?
C14 C15 1.3870(19) . ?
C15 C16 1.387(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.374(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.377(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.393(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.3209(19) . ?
C20 F20 1.3353(15) . ?
C21 F21 1.3435(15) . ?
C21 C22 1.456(2) . ?
C22 C23 1.323(2) . ?
C22 F22 1.3447(17) . ?
C23 F23 1.3474(15) . ?
C23 C24 1.450(2) . ?
C24 C25 1.3314(19) . ?
C24 F24 1.3463(16) . ?
C25 F25 1.3384(16) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C20 N1 C2 N3 167.87(12) . . . . ?
C5 N1 C2 N3 -0.05(14) . . . . ?
C20 N1 C2 C6 -12.3(2) . . . . ?
C5 N1 C2 C6 179.73(12) . . . . ?
N1 C2 N3 C4 0.14(15) . . . . ?
C6 C2 N3 C4 -179.64(12) . . . . ?
C2 N3 C4 C5 -0.19(15) . . . . ?
C2 N3 C4 C12 -179.06(12) . . . . ?
N3 C4 C5 N1 0.15(14) . . . . ?
C12 C4 C5 N1 178.87(13) . . . . ?
N3 C4 C5 C25 -176.73(13) . . . . ?
C12 C4 C5 C25 2.0(2) . . . . ?
C2 N1 C5 C4 -0.06(13) . . . . ?
C20 N1 C5 C4 -167.98(12) . . . . ?
C2 N1 C5 C25 177.15(12) . . . . ?
C20 N1 C5 C25 9.2(2) . . . . ?
N3 C2 C6 C11 150.34(14) . . . . ?
N1 C2 C6 C11 -29.4(2) . . . . ?
N3 C2 C6 C7 -26.50(19) . . . . ?
N1 C2 C6 C7 153.75(13) . . . . ?
C11 C6 C7 C8 0.5(2) . . . . ?
C2 C6 C7 C8 177.46(12) . . . . ?
C6 C7 C8 C9 0.1(2) . . . . ?
C7 C8 C9 C10 -0.1(2) . . . . ?
C8 C9 C10 C11 -0.6(2) . . . . ?
C9 C10 C11 C6 1.2(3) . . . . ?
C7 C6 C11 C10 -1.1(2) . . . . ?
C2 C6 C11 C10 -177.88(14) . . . . ?
C5 C4 C12 O12 -161.25(15) . . . . ?
N3 C4 C12 O12 17.4(2) . . . . ?
C5 C4 C12 O13 18.3(2) . . . . ?
N3 C4 C12 O13 -163.07(12) . . . . ?
O12 C12 O13 C13 9.5(2) . . . . ?
C4 C12 O13 C13 -170.05(12) . . . . ?
C14 C13 O13 C12 -109.50(14) . . . . ?
O13 C13 C14 C19 13.1(2) . . . . ?
O13 C13 C14 C15 -166.70(13) . . . . ?
C19 C14 C15 C16 1.4(2) . . . . ?
C13 C14 C15 C16 -178.80(15) . . . . ?
C14 C15 C16 C17 -1.0(3) . . . . ?
C15 C16 C17 C18 -0.3(3) . . . . ?
C16 C17 C18 C19 1.0(3) . . . . ?
C15 C14 C19 C18 -0.6(2) . . . . ?
C13 C14 C19 C18 179.61(14) . . . . ?
C17 C18 C19 C14 -0.6(3) . . . . ?
C2 N1 C20 C21 129.31(16) . . . . ?
C5 N1 C20 C21 -65.0(2) . . . . ?
C2 N1 C20 F20 -50.90(18) . . . . ?
C5 N1 C20 F20 114.77(14) . . . . ?
F20 C20 C21 F21 0.2(2) . . . . ?
N1 C20 C21 F21 179.99(13) . . . . ?
F20 C20 C21 C22 -179.01(13) . . . . ?
N1 C20 C21 C22 0.8(3) . . . . ?
C20 C21 C22 C23 61.0(2) . . . . ?
F21 C21 C22 C23 -118.24(16) . . . . ?
C20 C21 C22 F22 -119.19(17) . . . . ?
F21 C21 C22 F22 61.57(18) . . . . ?
F22 C22 C23 F23 -1.4(2) . . . . ?
C21 C22 C23 F23 178.43(12) . . . . ?
F22 C22 C23 C24 178.30(13) . . . . ?
C21 C22 C23 C24 -1.9(2) . . . . ?
C22 C23 C24 C25 -60.5(2) . . . . ?
F23 C23 C24 C25 119.14(14) . . . . ?
C22 C23 C24 F24 123.34(15) . . . . ?
F23 C23 C24 F24 -56.97(16) . . . . ?
F24 C24 C25 F25 1.12(18) . . . . ?
C23 C24 C25 F25 -174.84(11) . . . . ?
F24 C24 C25 C5 -179.00(11) . . . . ?
C23 C24 C25 C5 5.0(2) . . . . ?
C4 C5 C25 C24 -134.15(16) . . . . ?
N1 C5 C25 C24 49.5(2) . . . . ?
C4 C5 C25 F25 45.73(19) . . . . ?
N1 C5 C25 F25 -130.65(12) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659105
