#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:03:47 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178418 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/39/4023920.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_4023920
loop_
_publ_author_name
'Yun Ma'
'Sean Breslin'
'Ivan Keresztes'
'Emil Lobkovsky'
'David B. Collum'
_publ_section_title
;
 Synthesis of a 7-Azaindole by Chichibabin Cyclization:
 Reversible Base-Mediated Dimerization of 3-Picolines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9610
_journal_page_last               9618
_journal_paper_doi               10.1021/jo801410s
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C12 H10 F2 N2'
_chemical_formula_sum            'C12 H10 F2 N2'
_chemical_formula_weight         220.22
_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                92.050(4)
_cell_angle_beta                 95.711(4)
_cell_angle_gamma                94.074(4)
_cell_formula_units_Z            4
_cell_length_a                   7.3370(8)
_cell_length_b                   10.6664(11)
_cell_length_c                   13.1655(14)
_cell_measurement_reflns_used    7542
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.44
_cell_measurement_theta_min      2.80
_cell_volume                     1021.67(19)
_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      173(2)
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Bruker X8 APEX II diffractometer'
_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  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0330
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21945
_diffrn_reflns_theta_full        28.49
_diffrn_reflns_theta_max         28.49
_diffrn_reflns_theta_min         1.56
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.9565
_exptl_absorpt_correction_T_min  0.9461
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.743
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.513
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         5007
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.513
_refine_ls_R_factor_all          0.1012
_refine_ls_R_factor_gt           0.0767
_refine_ls_shift/su_max          0.051
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2157
_refine_ls_wR_factor_ref         0.2301
_reflns_number_gt                3596
_reflns_number_total             5007
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801410s_si_002.cif
_cod_data_source_block           ym1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4023920
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
F1 F 0.12086(13) 0.12644(9) 0.87184(8) 0.0327(3) Uani 1 1 d . . .
F2 F 0.48314(15) 0.67260(10) 0.60807(8) 0.0422(3) Uani 1 1 d . . .
F3 F 0.19721(13) 0.11484(9) 0.62657(8) 0.0378(3) Uani 1 1 d . . .
F4 F -0.15600(16) -0.43325(11) 0.90152(9) 0.0471(3) Uani 1 1 d . . .
N1 N 0.3972(2) 0.05051(13) 0.88431(11) 0.0322(4) Uani 1 1 d . . .
N2 N 0.47748(19) 0.73759(13) 0.77056(12) 0.0328(4) Uani 1 1 d . . .
N3 N -0.0842(2) 0.18292(13) 0.59819(12) 0.0342(4) Uani 1 1 d . . .
N4 N -0.15016(19) -0.49506(13) 0.73899(12) 0.0319(4) Uani 1 1 d . . .
C1 C 0.3050(2) 0.14815(15) 0.86951(12) 0.0240(4) Uani 1 1 d . . .
C2 C 0.5790(3) 0.06935(17) 0.88101(14) 0.0364(5) Uani 1 1 d . . .
H2 H 0.6527 0.0004 0.8919 0.044 Uiso 1 1 calc R . .
C3 C 0.6639(2) 0.18502(17) 0.86244(14) 0.0336(4) Uani 1 1 d . . .
H3 H 0.7932 0.1953 0.8605 0.040 Uiso 1 1 calc R . .
C4 C 0.5564(2) 0.28585(15) 0.84672(13) 0.0275(4) Uani 1 1 d . . .
H4 H 0.6123 0.3658 0.8332 0.033 Uiso 1 1 calc R . .
C5 C 0.3691(2) 0.27099(14) 0.85060(11) 0.0215(3) Uani 1 1 d . . .
C6 C 0.2371(2) 0.37195(14) 0.83617(14) 0.0282(4) Uani 1 1 d . . .
H6A H 0.1753 0.3817 0.8992 0.034 Uiso 1 1 calc R . .
H6B H 0.1416 0.3443 0.7798 0.034 Uiso 1 1 calc R . .
C7 C 0.3247(2) 0.49813(14) 0.81244(13) 0.0261(4) Uani 1 1 d . . .
C8 C 0.3699(2) 0.52165(15) 0.71528(13) 0.0260(4) Uani 1 1 d . . .
C9 C 0.4428(2) 0.64450(15) 0.70266(14) 0.0288(4) Uani 1 1 d . . .
C10 C 0.4350(2) 0.70950(16) 0.86445(15) 0.0347(5) Uani 1 1 d . . .
H10 H 0.4586 0.7735 0.9171 0.042 Uiso 1 1 calc R . .
C11 C 0.3595(2) 0.59425(16) 0.88939(14) 0.0300(4) Uani 1 1 d . . .
H11 H 0.3314 0.5799 0.9571 0.036 Uiso 1 1 calc R . .
C12 C 0.3432(3) 0.42574(17) 0.62844(14) 0.0360(5) Uani 1 1 d . . .
H12A H 0.4164(9) 0.3582(8) 0.6439(2) 0.054 Uiso 1 1 calc R . .
H12B H 0.3780(5) 0.4630(4) 0.5685(7) 0.054 Uiso 1 1 calc R . .
H12C H 0.2182(14) 0.3954(4) 0.61799(19) 0.054 Uiso 1 1 calc R . .
C13 C 0.0137(2) 0.08950(15) 0.62358(12) 0.0251(4) Uani 1 1 d . . .
C14 C -0.2666(3) 0.15938(18) 0.59524(14) 0.0375(5) Uani 1 1 d . . .
H14 H -0.3431 0.2249 0.5771 0.045 Uiso 1 1 calc R . .
C15 C -0.3479(2) 0.04511(18) 0.61717(14) 0.0351(5) Uani 1 1 d . . .
H15 H -0.4778 0.0319 0.6142 0.042 Uiso 1 1 calc R . .
C16 C -0.2361(2) -0.05120(16) 0.64390(13) 0.0293(4) Uani 1 1 d . . .
H16 H -0.2895 -0.1311 0.6593 0.035 Uiso 1 1 calc R . .
C17 C -0.0490(2) -0.03055(14) 0.64794(11) 0.0209(3) Uani 1 1 d . . .
C18 C 0.0872(2) -0.12709(14) 0.67560(13) 0.0259(4) Uani 1 1 d . . .
H18A H 0.1628 -0.1384 0.6182 0.031 Uiso 1 1 calc R . .
H18B H 0.1705 -0.0941 0.7359 0.031 Uiso 1 1 calc R . .
C19 C -0.0002(2) -0.25419(15) 0.69925(13) 0.0253(4) Uani 1 1 d . . .
C20 C -0.0438(2) -0.27927(15) 0.79632(13) 0.0273(4) Uani 1 1 d . . .
C21 C -0.1159(2) -0.40310(16) 0.80737(14) 0.0294(4) Uani 1 1 d . . .
C22 C -0.1087(2) -0.46542(16) 0.64511(14) 0.0326(4) Uani 1 1 d . . .
H22 H -0.1325 -0.5287 0.5918 0.039 Uiso 1 1 calc R . .
C23 C -0.0342(2) -0.34956(15) 0.62116(14) 0.0273(4) Uani 1 1 d . . .
H23 H -0.0062 -0.3341 0.5536 0.033 Uiso 1 1 calc R . .
C24 C -0.0192(3) -0.18669(19) 0.88443(15) 0.0417(5) Uani 1 1 d . . .
H24A H 0.0987(15) -0.1713(3) 0.9041(3) 0.063 Uiso 1 1 calc R . .
H24B H -0.0750(7) -0.2175(4) 0.9352(7) 0.063 Uiso 1 1 calc R . .
H24C H -0.0667(7) -0.1164(9) 0.8662(3) 0.063 Uiso 1 1 calc R . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 115.61(14) . . ?
C9 N2 C10 114.15(15) . . ?
C13 N3 C14 115.70(15) . . ?
C21 N4 C22 114.15(15) . . ?
N1 C1 F1 114.56(13) . . ?
N1 C1 C5 128.80(15) . . ?
F1 C1 C5 116.64(13) . . ?
N1 C2 C3 122.73(16) . . ?
C2 C3 C4 118.65(16) . . ?
C5 C4 C3 120.53(15) . . ?
C4 C5 C1 113.67(14) . . ?
C4 C5 C6 126.10(14) . . ?
C1 C5 C6 120.24(14) . . ?
C5 C6 C7 114.32(13) . . ?
C8 C7 C11 119.16(15) . . ?
C8 C7 C6 120.77(15) . . ?
C11 C7 C6 120.06(16) . . ?
C7 C8 C9 114.86(15) . . ?
C7 C8 C12 123.70(15) . . ?
C9 C8 C12 121.44(16) . . ?
N2 C9 F2 114.40(14) . . ?
N2 C9 C8 128.84(17) . . ?
F2 C9 C8 116.76(15) . . ?
N2 C10 C11 124.38(16) . . ?
C10 C11 C7 118.58(17) . . ?
N3 C13 F3 114.99(13) . . ?
N3 C13 C17 127.58(15) . . ?
F3 C13 C17 117.44(14) . . ?
N3 C14 C15 123.12(17) . . ?
C14 C15 C16 118.58(17) . . ?
C17 C16 C15 119.96(16) . . ?
C16 C17 C13 115.06(14) . . ?
C16 C17 C18 125.11(14) . . ?
C13 C17 C18 119.82(14) . . ?
C19 C18 C17 114.19(13) . . ?
C20 C19 C23 119.36(15) . . ?
C20 C19 C18 121.13(15) . . ?
C23 C19 C18 119.49(15) . . ?
C19 C20 C21 114.46(15) . . ?
C19 C20 C24 124.74(16) . . ?
C21 C20 C24 120.80(17) . . ?
N4 C21 F4 114.08(14) . . ?
N4 C21 C20 129.21(17) . . ?
F4 C21 C20 116.71(15) . . ?
N4 C22 C23 124.31(16) . . ?
C22 C23 C19 118.48(16) . . ?
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
F1 C1 1.3577(18) . ?
F2 C9 1.347(2) . ?
F3 C13 1.3504(18) . ?
F4 C21 1.347(2) . ?
N1 C1 1.292(2) . ?
N1 C2 1.340(2) . ?
N2 C9 1.306(2) . ?
N2 C10 1.344(2) . ?
N3 C13 1.304(2) . ?
N3 C14 1.340(2) . ?
N4 C21 1.301(2) . ?
N4 C22 1.345(2) . ?
C1 C5 1.400(2) . ?
C2 C3 1.383(3) . ?
C3 C4 1.388(2) . ?
C4 C5 1.378(2) . ?
C5 C6 1.503(2) . ?
C6 C7 1.506(2) . ?
C7 C8 1.380(2) . ?
C7 C11 1.407(2) . ?
C8 C9 1.402(2) . ?
C8 C12 1.495(2) . ?
C10 C11 1.376(2) . ?
C13 C17 1.389(2) . ?
C14 C15 1.372(3) . ?
C15 C16 1.393(2) . ?
C16 C17 1.370(2) . ?
C17 C18 1.514(2) . ?
C18 C19 1.514(2) . ?
C19 C20 1.379(2) . ?
C19 C23 1.411(2) . ?
C20 C21 1.406(2) . ?
C20 C24 1.485(3) . ?
C22 C23 1.375(2) . ?
