data_ym1

 

_audit_creation_method            SHELXL-97

_chemical_name_systematic

;

 ?

;

_chemical_name_common             ?

_chemical_melting_point           ?

_chemical_formula_moiety          
 'C12 H10 F2 N2'

_chemical_formula_sum

 'C12 H10 F2 N2'

_chemical_formula_weight          220.22

 

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'

 

_symmetry_cell_setting            Triclinic

_symmetry_space_group_name_H-M    P-1

 

loop_

 _symmetry_equiv_pos_as_xyz

 'x, y, z'

 '-x, -y, -z'

 

_cell_length_a                    7.3370(8)

_cell_length_b                    10.6664(11)

_cell_length_c                    13.1655(14)

_cell_angle_alpha                 92.050(4)

_cell_angle_beta                  95.711(4)

_cell_angle_gamma                 94.074(4)

_cell_volume                      1021.67(19)

_cell_formula_units_Z             4

_cell_measurement_temperature     173(2)

_cell_measurement_reflns_used     7542

_cell_measurement_theta_min       2.80

_cell_measurement_theta_max       28.44

 

_exptl_crystal_description        block

_exptl_crystal_colour             colourless

_exptl_crystal_size_max           0.50

_exptl_crystal_size_mid           0.45

_exptl_crystal_size_min           0.40

_exptl_crystal_density_meas       ?

_exptl_crystal_density_diffrn     1.432

_exptl_crystal_density_method     'not measured'

_exptl_crystal_F_000              456

_exptl_absorpt_coefficient_mu     0.112

_exptl_absorpt_correction_type    multi-scan

_exptl_absorpt_correction_T_min   0.9461

_exptl_absorpt_correction_T_max   0.9565

_exptl_absorpt_process_details    SADABS

 

_exptl_special_details

;

 ?

;

 

_diffrn_ambient_temperature       173(2)

_diffrn_radiation_wavelength      0.71073

_diffrn_radiation_type            MoK\a

_diffrn_radiation_source          'fine-focus sealed tube'

_diffrn_radiation_monochromator   graphite

_diffrn_measurement_device_type   'Bruker X8 APEX II diffractometer'

_diffrn_measurement_method        'phi and omega scans'

_diffrn_detector_area_resol_mean  ?

_diffrn_standards_number          ?

_diffrn_standards_interval_count  ?

_diffrn_standards_interval_time   ?

_diffrn_standards_decay_%         ?

_diffrn_reflns_number             21945

_diffrn_reflns_av_R_equivalents   0.0339

_diffrn_reflns_av_sigmaI/netI     0.0330

_diffrn_reflns_limit_h_min        -9

_diffrn_reflns_limit_h_max        9

_diffrn_reflns_limit_k_min        -14

_diffrn_reflns_limit_k_max        13

_diffrn_reflns_limit_l_min        -17

_diffrn_reflns_limit_l_max        17

_diffrn_reflns_theta_min          1.56

_diffrn_reflns_theta_max          28.49

_reflns_number_total              5007

_reflns_number_gt                 3596

_reflns_threshold_expression      >2sigma(I)

 

_computing_data_collection        'Bruker APEX2'

_computing_cell_refinement        'Bruker SAINT+'

_computing_data_reduction         'Bruker SAINT+'

_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics     'Bruker SHELXTL'

_computing_publication_material   'Bruker SHELXTL'

 

_refine_special_details

;

 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and

 goodness of fit S are based on F^2^, conventional R-factors R are based

 on F, with F set to zero for negative F^2^. The threshold expression of

 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is

 not relevant to the choice of reflections for refinement.  R-factors based

 on F^2^ are statistically about twice as large as those based on F, and R-

 factors based on ALL data will be even larger.

;

 

_refine_ls_structure_factor_coef  Fsqd

_refine_ls_matrix_type            full

_refine_ls_weighting_scheme       calc

_refine_ls_weighting_details

 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'

_atom_sites_solution_primary      direct

_atom_sites_solution_secondary    difmap

_atom_sites_solution_hydrogens    geom

_refine_ls_hydrogen_treatment     riding

_refine_ls_extinction_method      none

_refine_ls_extinction_coef        ?

_refine_ls_number_reflns          5007

_refine_ls_number_parameters      291

_refine_ls_number_restraints      0

_refine_ls_R_factor_all           0.1012

_refine_ls_R_factor_gt            0.0767

_refine_ls_wR_factor_ref          0.2301

_refine_ls_wR_factor_gt           0.2157

_refine_ls_goodness_of_fit_ref    1.513

_refine_ls_restrained_S_all       1.513

_refine_ls_shift/su_max           0.051

_refine_ls_shift/su_mean          0.003

 

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_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 0.0231(5) 0.0237(5) 0.0509(6) 0.0025(4) 0.0064(4) -0.0061(4)

F2 0.0455(6) 0.0379(6) 0.0449(6) 0.0127(5) 0.0101(5) 0.0018(5)

F3 0.0264(5) 0.0269(5) 0.0598(7) 0.0104(5) 0.0067(5) -0.0085(4)

F4 0.0536(7) 0.0435(6) 0.0457(7) 0.0117(5) 0.0119(5) -0.0016(5)

N1 0.0331(8) 0.0224(7) 0.0424(9) 0.0064(6) 0.0060(7) 0.0053(6)

N2 0.0224(7) 0.0263(7) 0.0501(9) 0.0052(7) 0.0030(7) 0.0039(6)

N3 0.0394(9) 0.0263(7) 0.0389(8) 0.0105(6) 0.0078(7) 0.0068(6)

N4 0.0207(7) 0.0288(7) 0.0464(9) 0.0069(6) 0.0017(6) 0.0037(6)

C1 0.0214(8) 0.0224(8) 0.0278(8) -0.0006(6) 0.0027(7) 0.0003(6)

C2 0.0357(10) 0.0330(9) 0.0444(11) 0.0102(8) 0.0089(8) 0.0180(7)

C3 0.0201(8) 0.0398(10) 0.0425(10) 0.0083(8) 0.0039(7) 0.0086(7)

C4 0.0227(8) 0.0243(8) 0.0353(9) 0.0038(7) 0.0024(7) -0.0013(6)

C5 0.0211(8) 0.0198(7) 0.0232(8) 0.0024(6) 0.0006(6) 0.0001(6)

C6 0.0195(8) 0.0173(7) 0.0484(10) 0.0062(7) 0.0047(7) 0.0019(6)

C7 0.0166(8) 0.0191(7) 0.0430(10) 0.0052(7) 0.0006(7) 0.0054(6)

C8 0.0192(8) 0.0218(8) 0.0369(9) -0.0001(7) -0.0009(7) 0.0056(6)

C9 0.0177(8) 0.0258(8) 0.0438(10) 0.0092(7) 0.0026(7) 0.0039(6)

C10 0.0270(9) 0.0239(9) 0.0510(11) -0.0055(8) -0.0028(8) -0.0003(7)

C11 0.0261(9) 0.0259(8) 0.0383(10) 0.0014(7) 0.0020(7) 0.0058(7)

C12 0.0364(10) 0.0318(9) 0.0390(10) -0.0019(8) 0.0001(8) 0.0035(8)

C13 0.0260(8) 0.0220(8) 0.0271(9) 0.0010(6) 0.0056(7) -0.0022(6)

C14 0.0393(10) 0.0357(10) 0.0401(11) 0.0101(8) 0.0061(8) 0.0147(8)

C15 0.0220(9) 0.0409(10) 0.0435(11) 0.0064(8) 0.0036(8) 0.0073(7)

C16 0.0218(8) 0.0264(8) 0.0394(10) 0.0041(7) 0.0026(7) 0.0002(7)

C17 0.0222(8) 0.0188(7) 0.0211(8) -0.0020(6) 0.0011(6) 0.0000(6)

C18 0.0187(8) 0.0205(7) 0.0387(9) 0.0045(7) 0.0038(7) -0.0005(6)

C19 0.0140(7) 0.0213(7) 0.0407(10) 0.0050(7) 0.0013(7) 0.0028(6)

C20 0.0207(8) 0.0249(8) 0.0362(9) 0.0006(7) 0.0011(7) 0.0028(6)

C21 0.0187(8) 0.0281(8) 0.0419(10) 0.0103(7) 0.0032(7) 0.0013(7)

C22 0.0267(9) 0.0251(9) 0.0439(11) -0.0035(7) -0.0034(8) 0.0004(7)

C23 0.0212(8) 0.0228(8) 0.0372(9) 0.0024(7) 0.0007(7) 0.0004(6)

C24 0.0423(11) 0.0390(11) 0.0439(11) -0.0050(8) 0.0066(9) 0.0040(9)

 

_geom_special_details

;

 All esds (except the esd in the dihedral angle between two l.s. planes)

 are estimated using the full covariance matrix.  The cell esds are taken

 into account individually in the estimation of esds in distances, angles

 and torsion angles; correlations between esds in cell parameters are only

 used when they are defined by crystal symmetry.  An approximate (isotropic)

 treatment of cell esds is used for estimating esds involving l.s. planes.

;

 

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) . ?

 

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) . . ?

 

_diffrn_measured_fraction_theta_max    0.967

_diffrn_reflns_theta_full              28.49

_diffrn_measured_fraction_theta_full   0.967

_refine_diff_density_max    0.743

_refine_diff_density_min   -0.316

_refine_diff_density_rms    0.084