# Supplementary Material (ESI) for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2010
data_global
_journal_coden_Cambridge 1350
_journal_volume ?
_journal_page_first ?
_journal_year ?
loop_
_publ_author_name
'Markus Albrecht'
'Michael Muller'
'Kari Rissanen'
'Arto Valkonen'
_publ_contact_author_name 'Markus Albrecht'
_publ_contact_author_email MARKUS.ALBRECHT@OC.RWTH-AACHEN.DE
_publ_section_title
;
Weak non-covalent interactions control the relative
molecular orientation in the crystals of N-pentafluorobenzyl
aniline derivatives
;
# Attachment 'Comp1.cif'
data_mm-80-3
_database_code_depnum_ccdc_archive 'CCDC 745348'
#TrackingRef 'Comp1.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C13 H8 F5 N'
_chemical_formula_sum 'C13 H8 F5 N'
_chemical_formula_weight 273.20
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 7.5435(5)
_cell_length_b 12.3178(7)
_cell_length_c 12.6712(8)
_cell_angle_alpha 98.008(5)
_cell_angle_beta 98.363(4)
_cell_angle_gamma 97.634(4)
_cell_volume 1139.35(12)
_cell_formula_units_Z 4
_cell_measurement_temperature 123.0(1)
_cell_measurement_reflns_used 4567
_cell_measurement_theta_max 28.283
_cell_measurement_theta_min 0.407
_exptl_crystal_description rod
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.22
_exptl_crystal_size_mid 0.10
_exptl_crystal_size_min 0.09
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.593
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 552
_exptl_absorpt_coefficient_mu 0.152
_exptl_absorpt_correction_type none
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_process_details ?
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 123.0(1)
_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-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 6821
_diffrn_reflns_av_R_equivalents 0.0637
_diffrn_reflns_av_sigmaI/netI 0.0937
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_l_min -13
_diffrn_reflns_limit_l_max 15
_diffrn_reflns_theta_min 2.16
_diffrn_reflns_theta_max 25.00
_reflns_number_total 3997
_reflns_number_gt 2363
_reflns_threshold_expression >2\s(I)
_computing_data_collection 'Collect (Bruker, 2008)'
_computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction DENZO-SMN
_computing_structure_solution 'SIR-2004 (Burla, et al., 2005)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997); MERCURY (Macrae, et al., 2006)'
_computing_publication_material SHELXL-97
_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^ > 2\s(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^)+(0.0121P)^2^+2.5213P] 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 mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 3997
_refine_ls_number_parameters 349
_refine_ls_number_restraints 2
_refine_ls_R_factor_all 0.1389
_refine_ls_R_factor_gt 0.0700
_refine_ls_wR_factor_ref 0.1417
_refine_ls_wR_factor_gt 0.1142
_refine_ls_goodness_of_fit_ref 1.066
_refine_ls_restrained_S_all 1.066
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
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 0.8961(4) 0.3808(3) 0.5645(2) 0.0550(9) Uani 1 1 d . . .
F2 F 0.8709(4) 0.5971(2) 0.6290(2) 0.0570(9) Uani 1 1 d . . .
F3 F 0.9971(4) 0.6925(2) 0.8366(2) 0.0491(8) Uani 1 1 d . . .
F4 F 1.1562(4) 0.5753(2) 0.9783(2) 0.0434(7) Uani 1 1 d . . .
F5 F 1.1853(4) 0.3627(2) 0.9162(2) 0.0421(7) Uani 1 1 d . . .
N1 N 0.8808(6) 0.1686(3) 0.6704(3) 0.0461(12) Uani 1 1 d D . .
H1 H 0.825(6) 0.167(4) 0.600(2) 0.055 Uiso 1 1 d D . .
C1 C 0.7640(7) 0.1507(3) 0.7456(4) 0.0321(11) Uani 1 1 d . . .
C2 C 0.8272(6) 0.1669(4) 0.8552(4) 0.0337(11) Uani 1 1 d . . .
H2 H 0.9519 0.1933 0.8822 0.040 Uiso 1 1 calc R . .
C3 C 0.7082(7) 0.1445(4) 0.9256(4) 0.0362(12) Uani 1 1 d . . .
H3 H 0.7524 0.1570 1.0011 0.043 Uiso 1 1 calc R . .
C4 C 0.5270(7) 0.1047(4) 0.8890(4) 0.0382(12) Uani 1 1 d . . .
H4 H 0.4465 0.0889 0.9379 0.046 Uiso 1 1 calc R . .
C5 C 0.4658(7) 0.0884(4) 0.7788(4) 0.0387(13) Uani 1 1 d . . .
H5 H 0.3411 0.0620 0.7518 0.046 Uiso 1 1 calc R . .
C6 C 0.5828(7) 0.1098(3) 0.7076(4) 0.0321(11) Uani 1 1 d . . .
H6 H 0.5388 0.0963 0.6321 0.039 Uiso 1 1 calc R . .
C7 C 1.0525(7) 0.2435(4) 0.7013(4) 0.0434(13) Uani 1 1 d . . .
H7A H 1.1170 0.2402 0.6385 0.052 Uiso 1 1 calc R . .
H7B H 1.1277 0.2163 0.7598 0.052 Uiso 1 1 calc R . .
C8 C 1.0379(6) 0.3633(4) 0.7393(4) 0.0288(11) Uani 1 1 d . . .
C9 C 0.9601(6) 0.4269(4) 0.6678(4) 0.0353(12) Uani 1 1 d . . .
C10 C 0.9461(6) 0.5373(4) 0.6994(4) 0.0349(12) Uani 1 1 d . . .
C11 C 1.0103(6) 0.5852(4) 0.8045(4) 0.0316(11) Uani 1 1 d . . .
C12 C 1.0894(6) 0.5260(4) 0.8756(4) 0.0297(11) Uani 1 1 d . . .
C13 C 1.1020(6) 0.4177(3) 0.8422(4) 0.0267(10) Uani 1 1 d . . .
F1A F 0.7790(4) 0.8694(2) 0.9176(2) 0.0386(7) Uani 1 1 d . . .
F2A F 1.0797(4) 0.9405(2) 0.8401(2) 0.0445(7) Uani 1 1 d . . .
F3A F 1.0670(4) 0.9378(2) 0.6239(2) 0.0446(7) Uani 1 1 d . . .
F4A F 0.7464(4) 0.8744(2) 0.4882(2) 0.0447(7) Uani 1 1 d . . .
F5A F 0.4433(3) 0.8055(2) 0.5640(2) 0.0394(7) Uani 1 1 d . . .
N1A N 0.4476(6) 0.6943(3) 0.8414(3) 0.0337(9) Uani 1 1 d D . .
H1A H 0.517(5) 0.710(4) 0.908(2) 0.040 Uiso 1 1 d D . .
C1A C 0.4706(6) 0.5930(3) 0.7838(4) 0.0260(10) Uani 1 1 d . . .
C2A C 0.4119(6) 0.5640(4) 0.6735(3) 0.0284(11) Uani 1 1 d . . .
H2A H 0.3624 0.6158 0.6334 0.034 Uiso 1 1 calc R . .
C3A C 0.4254(6) 0.4597(4) 0.6217(4) 0.0334(11) Uani 1 1 d . . .
H3A H 0.3849 0.4406 0.5459 0.040 Uiso 1 1 calc R . .
C4A C 0.4960(6) 0.3833(4) 0.6774(4) 0.0338(12) Uani 1 1 d . . .
H4A H 0.5043 0.3119 0.6407 0.041 Uiso 1 1 calc R . .
C5A C 0.5549(6) 0.4109(4) 0.7873(4) 0.0289(11) Uani 1 1 d . . .
H5A H 0.6034 0.3581 0.8265 0.035 Uiso 1 1 calc R . .
C6A C 0.5439(6) 0.5148(4) 0.8409(4) 0.0285(11) Uani 1 1 d . . .
H6A H 0.5860 0.5334 0.9165 0.034 Uiso 1 1 calc R . .
C7A C 0.4342(6) 0.7927(4) 0.7898(4) 0.0314(11) Uani 1 1 d . . .
H7A1 H 0.4118 0.8536 0.8435 0.038 Uiso 1 1 calc R . .
H7A2 H 0.3284 0.7759 0.7307 0.038 Uiso 1 1 calc R . .
C8A C 0.6024(6) 0.8326(3) 0.7437(3) 0.0255(10) Uani 1 1 d . . .
C9A C 0.7668(6) 0.8684(3) 0.8101(3) 0.0256(10) Uani 1 1 d . . .
C10A C 0.9227(6) 0.9051(3) 0.7727(4) 0.0290(11) Uani 1 1 d . . .
C11A C 0.9162(6) 0.9047(3) 0.6638(4) 0.0274(10) Uani 1 1 d . . .
C12A C 0.7539(6) 0.8705(3) 0.5949(3) 0.0270(10) Uani 1 1 d . . .
C13A C 0.6006(6) 0.8354(3) 0.6359(4) 0.0281(10) Uani 1 1 d . . .
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 0.058(2) 0.070(2) 0.0291(17) 0.0034(14) 0.0055(15) -0.0108(17)
F2 0.0483(19) 0.063(2) 0.061(2) 0.0340(17) -0.0056(16) 0.0031(16)
F3 0.0480(19) 0.0307(16) 0.070(2) 0.0058(14) 0.0118(16) 0.0110(14)
F4 0.0537(19) 0.0353(15) 0.0345(17) -0.0022(12) 0.0055(14) -0.0066(14)
F5 0.0389(17) 0.0360(16) 0.0492(18) 0.0165(13) -0.0039(14) 0.0007(13)
N1 0.055(3) 0.037(2) 0.039(3) -0.008(2) 0.015(2) -0.011(2)
C1 0.043(3) 0.015(2) 0.040(3) 0.002(2) 0.017(2) 0.003(2)
C2 0.028(3) 0.026(2) 0.043(3) 0.001(2) -0.001(2) 0.002(2)
C3 0.051(3) 0.027(3) 0.029(3) 0.004(2) 0.006(2) 0.005(2)
C4 0.047(3) 0.025(3) 0.044(3) 0.004(2) 0.018(3) 0.001(2)
C5 0.028(3) 0.022(2) 0.064(4) 0.007(2) 0.002(3) 0.003(2)
C6 0.045(3) 0.019(2) 0.029(3) -0.0004(19) -0.002(2) 0.006(2)
C7 0.038(3) 0.036(3) 0.057(3) -0.003(2) 0.029(3) -0.003(2)
C8 0.024(3) 0.026(2) 0.037(3) 0.003(2) 0.015(2) 0.000(2)
C9 0.028(3) 0.050(3) 0.022(3) 0.003(2) 0.003(2) -0.010(2)
C10 0.023(3) 0.039(3) 0.045(3) 0.022(2) 0.000(2) 0.002(2)
C11 0.024(3) 0.024(3) 0.048(3) 0.007(2) 0.011(2) 0.005(2)
C12 0.028(3) 0.026(2) 0.034(3) 0.002(2) 0.010(2) -0.002(2)
C13 0.018(2) 0.028(3) 0.035(3) 0.010(2) 0.004(2) 0.003(2)
F1A 0.0437(17) 0.0420(16) 0.0309(16) 0.0081(12) 0.0072(13) 0.0059(13)
F2A 0.0309(16) 0.0514(18) 0.0462(18) 0.0100(14) -0.0045(14) -0.0016(14)
F3A 0.0340(17) 0.0508(18) 0.0529(18) 0.0120(14) 0.0201(14) 0.0022(14)
F4A 0.0479(18) 0.0563(18) 0.0287(16) 0.0059(13) 0.0089(13) 0.0024(15)
F5A 0.0303(16) 0.0472(17) 0.0360(16) 0.0063(13) -0.0009(13) -0.0033(13)
N1A 0.042(3) 0.031(2) 0.027(2) 0.0050(18) 0.0082(18) -0.0011(19)
C1A 0.022(2) 0.021(2) 0.036(3) 0.0035(19) 0.013(2) -0.0012(19)
C2A 0.024(3) 0.031(3) 0.030(3) 0.009(2) 0.005(2) -0.002(2)
C3A 0.029(3) 0.037(3) 0.029(3) 0.002(2) 0.004(2) -0.009(2)
C4A 0.026(3) 0.028(3) 0.047(3) 0.002(2) 0.012(2) 0.001(2)
C5A 0.019(2) 0.031(3) 0.038(3) 0.012(2) 0.003(2) 0.006(2)
C6A 0.020(2) 0.034(3) 0.028(3) 0.008(2) -0.002(2) -0.002(2)
C7A 0.027(3) 0.028(2) 0.042(3) 0.007(2) 0.014(2) 0.004(2)
C8A 0.031(3) 0.018(2) 0.029(3) 0.0020(18) 0.007(2) 0.007(2)
C9A 0.034(3) 0.023(2) 0.022(2) 0.0067(18) 0.006(2) 0.006(2)
C10A 0.026(3) 0.025(2) 0.033(3) 0.002(2) -0.004(2) 0.004(2)
C11A 0.022(3) 0.024(2) 0.039(3) 0.006(2) 0.013(2) 0.005(2)
C12A 0.034(3) 0.027(2) 0.023(3) 0.0058(19) 0.009(2) 0.007(2)
C13A 0.028(3) 0.018(2) 0.036(3) -0.0009(19) 0.004(2) 0.002(2)
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 C9 1.344(5) . ?
F2 C10 1.344(5) . ?
F3 C11 1.349(5) . ?
F4 C12 1.350(5) . ?
F5 C13 1.361(5) . ?
N1 C1 1.409(6) . ?
N1 C7 1.454(6) . ?
N1 H1 0.923(19) . ?
C1 C2 1.379(6) . ?
C1 C6 1.383(6) . ?
C2 C3 1.384(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.378(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.377(7) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.511(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C13 1.367(6) . ?
C8 C9 1.394(6) . ?
C9 C10 1.386(7) . ?
C10 C11 1.369(7) . ?
C11 C12 1.358(6) . ?
C12 C13 1.362(6) . ?
F1A C9A 1.350(5) . ?
F2A C10A 1.337(5) . ?
F3A C11A 1.348(5) . ?
F4A C12A 1.353(5) . ?
F5A C13A 1.360(5) . ?
N1A C1A 1.400(6) . ?
N1A C7A 1.464(5) . ?
N1A H1A 0.901(19) . ?
C1A C2A 1.384(6) . ?
C1A C6A 1.406(6) . ?
C2A C3A 1.383(6) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.370(6) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.378(6) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.382(6) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C7A C8A 1.524(6) . ?
C7A H7A1 0.9900 . ?
C7A H7A2 0.9900 . ?
C8A C13A 1.369(6) . ?
C8A C9A 1.375(6) . ?
C9A C10A 1.376(6) . ?
C10A C11A 1.373(6) . ?
C11A C12A 1.374(6) . ?
C12A C13A 1.378(6) . ?
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 C7 121.3(4) . . ?
C1 N1 H1 116(3) . . ?
C7 N1 H1 114(3) . . ?
C2 C1 C6 119.3(4) . . ?
C2 C1 N1 121.8(4) . . ?
C6 C1 N1 118.8(4) . . ?
C1 C2 C3 119.7(4) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 121.6(5) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 118.0(5) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 H4 121.0 . . ?
C6 C5 C4 121.1(5) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 120.3(4) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
N1 C7 C8 115.3(4) . . ?
N1 C7 H7A 108.4 . . ?
C8 C7 H7A 108.4 . . ?
N1 C7 H7B 108.4 . . ?
C8 C7 H7B 108.4 . . ?
H7A C7 H7B 107.5 . . ?
C13 C8 C9 115.5(4) . . ?
C13 C8 C7 123.9(4) . . ?
C9 C8 C7 120.6(4) . . ?
F1 C9 C10 118.2(4) . . ?
F1 C9 C8 119.6(4) . . ?
C10 C9 C8 122.3(4) . . ?
F2 C10 C11 120.1(4) . . ?
F2 C10 C9 121.2(4) . . ?
C11 C10 C9 118.7(4) . . ?
F3 C11 C12 120.1(4) . . ?
F3 C11 C10 119.5(4) . . ?
C12 C11 C10 120.5(4) . . ?
F4 C12 C11 119.7(4) . . ?
F4 C12 C13 120.8(4) . . ?
C11 C12 C13 119.5(4) . . ?
F5 C13 C12 117.1(4) . . ?
F5 C13 C8 119.3(4) . . ?
C12 C13 C8 123.6(4) . . ?
C1A N1A C7A 121.9(4) . . ?
C1A N1A H1A 112(3) . . ?
C7A N1A H1A 113(3) . . ?
C2A C1A N1A 122.2(4) . . ?
C2A C1A C6A 118.8(4) . . ?
N1A C1A C6A 118.9(4) . . ?
C3A C2A C1A 120.0(4) . . ?
C3A C2A H2A 120.0 . . ?
C1A C2A H2A 120.0 . . ?
C4A C3A C2A 121.3(4) . . ?
C4A C3A H3A 119.4 . . ?
C2A C3A H3A 119.4 . . ?
C3A C4A C5A 119.4(4) . . ?
C3A C4A H4A 120.3 . . ?
C5A C4A H4A 120.3 . . ?
C4A C5A C6A 120.4(4) . . ?
C4A C5A H5A 119.8 . . ?
C6A C5A H5A 119.8 . . ?
C5A C6A C1A 120.2(4) . . ?
C5A C6A H6A 119.9 . . ?
C1A C6A H6A 119.9 . . ?
N1A C7A C8A 114.0(4) . . ?
N1A C7A H7A1 108.8 . . ?
C8A C7A H7A1 108.8 . . ?
N1A C7A H7A2 108.8 . . ?
C8A C7A H7A2 108.8 . . ?
H7A1 C7A H7A2 107.7 . . ?
C13A C8A C9A 116.1(4) . . ?
C13A C8A C7A 123.1(4) . . ?
C9A C8A C7A 120.8(4) . . ?
F1A C9A C8A 119.6(4) . . ?
F1A C9A C10A 117.3(4) . . ?
C8A C9A C10A 123.1(4) . . ?
F2A C10A C11A 119.6(4) . . ?
F2A C10A C9A 121.3(4) . . ?
C11A C10A C9A 119.1(4) . . ?
F3A C11A C10A 120.7(4) . . ?
F3A C11A C12A 119.7(4) . . ?
C10A C11A C12A 119.6(4) . . ?
F4A C12A C11A 119.4(4) . . ?
F4A C12A C13A 121.1(4) . . ?
C11A C12A C13A 119.5(4) . . ?
F5A C13A C8A 120.6(4) . . ?
F5A C13A C12A 116.6(4) . . ?
C8A C13A C12A 122.7(4) . . ?
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
C7 N1 C1 C2 -24.5(7) . . . . ?
C7 N1 C1 C6 159.2(4) . . . . ?
C6 C1 C2 C3 -1.5(6) . . . . ?
N1 C1 C2 C3 -177.8(4) . . . . ?
C1 C2 C3 C4 0.9(7) . . . . ?
C2 C3 C4 C5 -0.6(7) . . . . ?
C3 C4 C5 C6 0.9(7) . . . . ?
C4 C5 C6 C1 -1.5(7) . . . . ?
C2 C1 C6 C5 1.8(6) . . . . ?
N1 C1 C6 C5 178.2(4) . . . . ?
C1 N1 C7 C8 -62.1(6) . . . . ?
N1 C7 C8 C13 114.9(5) . . . . ?
N1 C7 C8 C9 -66.9(6) . . . . ?
C13 C8 C9 F1 178.9(4) . . . . ?
C7 C8 C9 F1 0.6(6) . . . . ?
C13 C8 C9 C10 -1.0(6) . . . . ?
C7 C8 C9 C10 -179.3(4) . . . . ?
F1 C9 C10 F2 -0.1(7) . . . . ?
C8 C9 C10 F2 179.8(4) . . . . ?
F1 C9 C10 C11 179.8(4) . . . . ?
C8 C9 C10 C11 -0.3(7) . . . . ?
F2 C10 C11 F3 0.1(6) . . . . ?
C9 C10 C11 F3 -179.8(4) . . . . ?
F2 C10 C11 C12 -178.8(4) . . . . ?
C9 C10 C11 C12 1.4(7) . . . . ?
F3 C11 C12 F4 -0.6(6) . . . . ?
C10 C11 C12 F4 178.3(4) . . . . ?
F3 C11 C12 C13 -179.9(4) . . . . ?
C10 C11 C12 C13 -1.1(7) . . . . ?
F4 C12 C13 F5 -0.4(6) . . . . ?
C11 C12 C13 F5 178.9(4) . . . . ?
F4 C12 C13 C8 -179.6(4) . . . . ?
C11 C12 C13 C8 -0.3(7) . . . . ?
C9 C8 C13 F5 -177.9(4) . . . . ?
C7 C8 C13 F5 0.4(6) . . . . ?
C9 C8 C13 C12 1.3(6) . . . . ?
C7 C8 C13 C12 179.6(4) . . . . ?
C7A N1A C1A C2A -26.4(6) . . . . ?
C7A N1A C1A C6A 158.2(4) . . . . ?
N1A C1A C2A C3A -175.1(4) . . . . ?
C6A C1A C2A C3A 0.2(6) . . . . ?
C1A C2A C3A C4A 0.1(7) . . . . ?
C2A C3A C4A C5A 0.0(7) . . . . ?
C3A C4A C5A C6A -0.3(6) . . . . ?
C4A C5A C6A C1A 0.6(6) . . . . ?
C2A C1A C6A C5A -0.6(6) . . . . ?
N1A C1A C6A C5A 174.9(4) . . . . ?
C1A N1A C7A C8A -61.5(6) . . . . ?
N1A C7A C8A C13A 117.4(5) . . . . ?
N1A C7A C8A C9A -62.7(5) . . . . ?
C13A C8A C9A F1A 179.2(4) . . . . ?
C7A C8A C9A F1A -0.7(6) . . . . ?
C13A C8A C9A C10A -0.2(6) . . . . ?
C7A C8A C9A C10A 179.9(4) . . . . ?
F1A C9A C10A F2A -0.2(6) . . . . ?
C8A C9A C10A F2A 179.2(4) . . . . ?
F1A C9A C10A C11A 179.6(4) . . . . ?
C8A C9A C10A C11A -1.0(6) . . . . ?
F2A C10A C11A F3A 1.2(6) . . . . ?
C9A C10A C11A F3A -178.6(4) . . . . ?
F2A C10A C11A C12A -178.6(4) . . . . ?
C9A C10A C11A C12A 1.6(6) . . . . ?
F3A C11A C12A F4A -2.4(6) . . . . ?
C10A C11A C12A F4A 177.4(4) . . . . ?
F3A C11A C12A C13A 179.2(4) . . . . ?
C10A C11A C12A C13A -1.0(6) . . . . ?
C9A C8A C13A F5A -177.6(4) . . . . ?
C7A C8A C13A F5A 2.3(6) . . . . ?
C9A C8A C13A C12A 0.8(6) . . . . ?
C7A C8A C13A C12A -179.3(4) . . . . ?
F4A C12A C13A F5A -0.1(6) . . . . ?
C11A C12A C13A F5A 178.2(4) . . . . ?
F4A C12A C13A C8A -178.6(4) . . . . ?
C11A C12A C13A C8A -0.2(6) . . . . ?
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max 0.404
_refine_diff_density_min -0.270
_refine_diff_density_rms 0.066
# Attachment 'Comp2.cif'
data_mm-80-7
_database_code_depnum_ccdc_archive 'CCDC 745349'
#TrackingRef 'Comp2.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C13 H9 F5 N, Br'
_chemical_formula_sum 'C13 H9 Br F5 N'
_chemical_formula_weight 354.12
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M Pc
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
_cell_length_a 11.5483(3)
_cell_length_b 7.7905(2)
_cell_length_c 7.7488(2)
_cell_angle_alpha 90.00
_cell_angle_beta 101.708(2)
_cell_angle_gamma 90.00
_cell_volume 682.63(3)
_cell_formula_units_Z 2
_cell_measurement_temperature 123.0(1)
_cell_measurement_reflns_used 1748
_cell_measurement_theta_max 28.283
_cell_measurement_theta_min 0.407
_exptl_crystal_description prism
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.48
_exptl_crystal_size_mid 0.42
_exptl_crystal_size_min 0.41
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.723
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 348
_exptl_absorpt_coefficient_mu 3.056
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.2152
_exptl_absorpt_correction_T_max 0.2833
_exptl_absorpt_process_details 'Sadabs (Sheldrick, 1996)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 123(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 Kappa APEX-II'
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 7487
_diffrn_reflns_av_R_equivalents 0.0304
_diffrn_reflns_av_sigmaI/netI 0.0423
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 13
_diffrn_reflns_limit_k_min -9
_diffrn_reflns_limit_k_max 9
_diffrn_reflns_limit_l_min -9
_diffrn_reflns_limit_l_max 9
_diffrn_reflns_theta_min 2.61
_diffrn_reflns_theta_max 25.01
_reflns_number_total 2018
_reflns_number_gt 1921
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'Collect (Bruker, 2004)'
_computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution 'SIR-2002 (Burla, et al., 2003)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
'SHELXL-97; MERCURY (Macrae, et al., 2006)'
_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^)+(0.0000P)^2^+0.0548P] 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 mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.040(8)
_refine_ls_number_reflns 2018
_refine_ls_number_parameters 188
_refine_ls_number_restraints 4
_refine_ls_R_factor_all 0.0223
_refine_ls_R_factor_gt 0.0201
_refine_ls_wR_factor_ref 0.0445
_refine_ls_wR_factor_gt 0.0438
_refine_ls_goodness_of_fit_ref 1.080
_refine_ls_restrained_S_all 1.079
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
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
Br1 Br 0.61121(4) 0.28334(3) 0.40861(4) 0.02905(9) Uani 1 1 d . . .
F1 F 0.44581(14) 0.02296(19) 0.6133(2) 0.0278(4) Uani 1 1 d . . .
F2 F 0.21810(15) 0.0637(2) 0.4567(2) 0.0342(4) Uani 1 1 d . . .
F3 F 0.07960(14) 0.2877(2) 0.5923(2) 0.0324(4) Uani 1 1 d . . .
F4 F 0.17516(16) 0.4786(2) 0.8795(2) 0.0386(4) Uani 1 1 d . . .
F5 F 0.40347(15) 0.4407(2) 1.0347(2) 0.0318(4) Uani 1 1 d . . .
N1 N 0.64369(19) 0.3122(3) 0.8335(3) 0.0156(5) Uani 1 1 d D . .
H1A H 0.632(2) 0.425(2) 0.846(3) 0.019 Uiso 1 1 d D . .
H1B H 0.629(3) 0.294(3) 0.716(2) 0.019 Uiso 1 1 d D . .
C1 C 0.7680(3) 0.2732(4) 0.9111(4) 0.0174(6) Uani 1 1 d . . .
C2 C 0.8280(3) 0.1513(4) 0.8348(4) 0.0362(7) Uani 1 1 d . . .
H2 H 0.7902 0.0933 0.7306 0.043 Uiso 1 1 calc R . .
C3 C 0.9436(3) 0.1148(5) 0.9122(5) 0.0467(9) Uani 1 1 d . . .
H3 H 0.9853 0.0298 0.8614 0.056 Uiso 1 1 calc R . .
C4 C 0.9994(3) 0.1991(4) 1.0612(5) 0.0372(8) Uani 1 1 d . . .
H4 H 1.0795 0.1737 1.1123 0.045 Uiso 1 1 calc R . .
C5 C 0.9387(3) 0.3211(4) 1.1366(5) 0.0406(9) Uani 1 1 d . . .
H5 H 0.9766 0.3792 1.2405 0.049 Uiso 1 1 calc R . .
C6 C 0.8227(3) 0.3585(4) 1.0609(4) 0.0327(7) Uani 1 1 d . . .
H6 H 0.7808 0.4429 1.1122 0.039 Uiso 1 1 calc R . .
C7 C 0.5604(2) 0.2055(3) 0.9150(4) 0.0169(6) Uani 1 1 d . . .
H7A H 0.5801 0.0826 0.9061 0.020 Uiso 1 1 calc R . .
H7B H 0.5708 0.2347 1.0416 0.020 Uiso 1 1 calc R . .
C8 C 0.4338(2) 0.2346(4) 0.8264(4) 0.0158(6) Uani 1 1 d . . .
C9 C 0.3812(2) 0.1393(3) 0.6792(3) 0.0185(5) Uani 1 1 d . . .
C10 C 0.2638(2) 0.1575(3) 0.5994(4) 0.0230(6) Uani 1 1 d . . .
C11 C 0.1939(3) 0.2710(3) 0.6666(4) 0.0231(6) Uani 1 1 d . . .
C12 C 0.2428(2) 0.3664(3) 0.8134(4) 0.0232(6) Uani 1 1 d . . .
C13 C 0.3607(2) 0.3476(3) 0.8913(3) 0.0197(6) Uani 1 1 d . . .
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
Br1 0.05303(17) 0.01773(13) 0.01543(12) -0.00067(18) 0.00464(10) -0.0059(2)
F1 0.0271(10) 0.0258(9) 0.0308(9) -0.0106(7) 0.0066(7) 0.0025(7)
F2 0.0287(10) 0.0435(10) 0.0275(9) -0.0163(7) -0.0014(7) -0.0078(7)
F3 0.0166(9) 0.0426(10) 0.0346(10) 0.0003(7) -0.0028(7) 0.0022(7)
F4 0.0265(10) 0.0459(11) 0.0422(11) -0.0154(8) 0.0037(8) 0.0145(8)
F5 0.0293(9) 0.0373(9) 0.0258(9) -0.0163(7) -0.0016(7) 0.0048(7)
N1 0.0180(12) 0.0151(11) 0.0125(11) 0.0005(9) 0.0003(9) 0.0019(8)
C1 0.0149(15) 0.0229(15) 0.0145(16) 0.0033(11) 0.0036(12) -0.0027(11)
C2 0.0329(18) 0.0447(19) 0.0280(17) -0.0112(15) -0.0005(13) 0.0111(14)
C3 0.0310(19) 0.067(2) 0.040(2) -0.0081(17) 0.0030(15) 0.0244(17)
C4 0.0172(18) 0.049(2) 0.045(2) 0.0145(16) 0.0061(15) 0.0029(14)
C5 0.031(2) 0.043(2) 0.042(2) -0.0079(15) -0.0064(16) -0.0031(15)
C6 0.0280(18) 0.0303(17) 0.0365(18) -0.0088(14) -0.0009(14) 0.0025(13)
C7 0.0181(13) 0.0169(14) 0.0161(13) 0.0025(10) 0.0047(11) -0.0012(10)
C8 0.0180(16) 0.0186(14) 0.0114(15) 0.0040(12) 0.0040(12) 0.0008(11)
C9 0.0219(15) 0.0167(13) 0.0178(13) -0.0023(11) 0.0064(11) -0.0008(11)
C10 0.0257(16) 0.0228(14) 0.0203(14) -0.0041(12) 0.0043(11) -0.0063(12)
C11 0.0169(16) 0.0250(15) 0.0262(16) 0.0051(13) 0.0016(12) -0.0020(13)
C12 0.0210(15) 0.0246(15) 0.0247(15) -0.0020(12) 0.0060(12) 0.0046(12)
C13 0.0245(15) 0.0181(13) 0.0154(13) -0.0024(11) 0.0016(11) -0.0028(11)
_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 C9 1.339(3) . ?
F2 C10 1.341(3) . ?
F3 C11 1.335(4) . ?
F4 C12 1.341(3) . ?
F5 C13 1.334(3) . ?
N1 C1 1.471(4) . ?
N1 C7 1.504(3) . ?
N1 H1A 0.900(17) . ?
N1 H1B 0.905(18) . ?
C1 C6 1.375(4) . ?
C1 C2 1.378(4) . ?
C2 C3 1.378(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.370(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.379(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.380(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.501(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C13 1.384(4) . ?
C8 C9 1.392(4) . ?
C9 C10 1.379(4) . ?
C10 C11 1.369(4) . ?
C11 C12 1.380(4) . ?
C12 C13 1.380(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 C7 111.6(2) . . ?
C1 N1 H1A 108.5(18) . . ?
C7 N1 H1A 111.8(16) . . ?
C1 N1 H1B 110.5(19) . . ?
C7 N1 H1B 109.3(18) . . ?
H1A N1 H1B 105(2) . . ?
C6 C1 C2 120.7(3) . . ?
C6 C1 N1 119.3(3) . . ?
C2 C1 N1 120.0(3) . . ?
C3 C2 C1 118.8(3) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C4 C3 C2 121.1(3) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 119.7(3) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 119.9(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 119.8(3) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C8 C7 N1 111.8(2) . . ?
C8 C7 H7A 109.3 . . ?
N1 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
N1 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
C13 C8 C9 116.1(3) . . ?
C13 C8 C7 122.6(3) . . ?
C9 C8 C7 121.1(2) . . ?
F1 C9 C10 118.2(2) . . ?
F1 C9 C8 119.3(2) . . ?
C10 C9 C8 122.6(2) . . ?
F2 C10 C11 120.2(2) . . ?
F2 C10 C9 120.0(2) . . ?
C11 C10 C9 119.8(2) . . ?
F3 C11 C10 120.4(3) . . ?
F3 C11 C12 120.4(2) . . ?
C10 C11 C12 119.2(3) . . ?
F4 C12 C11 119.5(2) . . ?
F4 C12 C13 120.1(2) . . ?
C11 C12 C13 120.4(2) . . ?
F5 C13 C12 118.2(2) . . ?
F5 C13 C8 119.9(2) . . ?
C12 C13 C8 121.9(2) . . ?
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
C7 N1 C1 C6 -86.9(3) . . . . ?
C7 N1 C1 C2 92.5(3) . . . . ?
C6 C1 C2 C3 0.7(5) . . . . ?
N1 C1 C2 C3 -178.7(3) . . . . ?
C1 C2 C3 C4 -0.8(6) . . . . ?
C2 C3 C4 C5 0.8(6) . . . . ?
C3 C4 C5 C6 -0.6(5) . . . . ?
C2 C1 C6 C5 -0.4(5) . . . . ?
N1 C1 C6 C5 178.9(3) . . . . ?
C4 C5 C6 C1 0.4(5) . . . . ?
C1 N1 C7 C8 -175.4(2) . . . . ?
N1 C7 C8 C13 -96.6(3) . . . . ?
N1 C7 C8 C9 87.7(3) . . . . ?
C13 C8 C9 F1 -177.6(2) . . . . ?
C7 C8 C9 F1 -1.7(4) . . . . ?
C13 C8 C9 C10 1.1(4) . . . . ?
C7 C8 C9 C10 177.1(2) . . . . ?
F1 C9 C10 F2 -2.0(4) . . . . ?
C8 C9 C10 F2 179.3(2) . . . . ?
F1 C9 C10 C11 177.8(2) . . . . ?
C8 C9 C10 C11 -1.0(4) . . . . ?
F2 C10 C11 F3 0.8(4) . . . . ?
C9 C10 C11 F3 -178.9(2) . . . . ?
F2 C10 C11 C12 -179.9(3) . . . . ?
C9 C10 C11 C12 0.4(4) . . . . ?
F3 C11 C12 F4 -1.1(4) . . . . ?
C10 C11 C12 F4 179.6(3) . . . . ?
F3 C11 C12 C13 179.3(2) . . . . ?
C10 C11 C12 C13 0.0(4) . . . . ?
F4 C12 C13 F5 1.4(4) . . . . ?
C11 C12 C13 F5 -178.9(2) . . . . ?
F4 C12 C13 C8 -179.4(3) . . . . ?
C11 C12 C13 C8 0.2(4) . . . . ?
C9 C8 C13 F5 178.4(2) . . . . ?
C7 C8 C13 F5 2.5(4) . . . . ?
C9 C8 C13 C12 -0.8(4) . . . . ?
C7 C8 C13 C12 -176.6(2) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A Br1 0.900(17) 2.343(18) 3.240(2) 174(2) 2_565
N1 H1B Br1 0.905(18) 2.348(19) 3.245(2) 171(2) .
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 25.01
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max 0.209
_refine_diff_density_min -0.274
_refine_diff_density_rms 0.045
# Attachment 'Comp3.cif'
data_mm-82-1
_database_code_depnum_ccdc_archive 'CCDC 745350'
#TrackingRef 'Comp3.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C13 H8 Br F5 N, Cl'
_chemical_formula_sum 'C13 H8 Br Cl F5 N'
_chemical_formula_weight 388.56
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M P21/n
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a 14.1734(3)
_cell_length_b 7.3775(2)
_cell_length_c 14.4255(3)
_cell_angle_alpha 90.00
_cell_angle_beta 112.497(2)
_cell_angle_gamma 90.00
_cell_volume 1393.60(6)
_cell_formula_units_Z 4
_cell_measurement_temperature 123.0(1)
_cell_measurement_reflns_used 3189
_cell_measurement_theta_max 26.733
_cell_measurement_theta_min 0.407
_exptl_crystal_description plate
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.28
_exptl_crystal_size_mid 0.22
_exptl_crystal_size_min 0.11
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.852
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 760
_exptl_absorpt_coefficient_mu 3.189
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.4761
_exptl_absorpt_correction_T_max 0.7009
_exptl_absorpt_process_details 'Sadabs (Sheldrick, 1996)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 123.0(1)
_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 Kappa APEX-II'
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 15241
_diffrn_reflns_av_R_equivalents 0.0399
_diffrn_reflns_av_sigmaI/netI 0.0299
_diffrn_reflns_limit_h_min -16
_diffrn_reflns_limit_h_max 16
_diffrn_reflns_limit_k_min -6
_diffrn_reflns_limit_k_max 8
_diffrn_reflns_limit_l_min -17
_diffrn_reflns_limit_l_max 17
_diffrn_reflns_theta_min 3.06
_diffrn_reflns_theta_max 25.00
_reflns_number_total 2448
_reflns_number_gt 2143
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'Collect (Bruker, 2004)'
_computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution 'SIR-2002 (Burla, et al., 2003)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
'SHELXL-97; MERCURY (Macrae, et al., 2006)'
_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^)+(0.0000P)^2^+1.6403P] 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 mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 2448
_refine_ls_number_parameters 196
_refine_ls_number_restraints 2
_refine_ls_R_factor_all 0.0305
_refine_ls_R_factor_gt 0.0235
_refine_ls_wR_factor_ref 0.0519
_refine_ls_wR_factor_gt 0.0492
_refine_ls_goodness_of_fit_ref 1.051
_refine_ls_restrained_S_all 1.050
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
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
Br1 Br 0.689965(19) 0.47295(3) 0.235764(17) 0.02556(9) Uani 1 1 d . . .
Cl1 Cl 0.65691(4) -0.08092(8) 0.66526(4) 0.02395(14) Uani 1 1 d . . .
F1 F 0.46035(10) 0.12700(18) 0.66459(10) 0.0271(3) Uani 1 1 d . . .
F2 F 0.44972(11) 0.0084(2) 0.83681(11) 0.0360(4) Uani 1 1 d . . .
F3 F 0.53359(12) 0.2091(2) 1.00725(11) 0.0387(4) Uani 1 1 d . . .
F4 F 0.63068(11) 0.5242(2) 1.00435(10) 0.0355(4) Uani 1 1 d . . .
F5 F 0.64399(10) 0.64011(18) 0.83333(10) 0.0265(3) Uani 1 1 d . . .
N1 N 0.65980(15) 0.3357(3) 0.64042(14) 0.0177(4) Uani 1 1 d D . .
H1A H 0.7169(14) 0.367(3) 0.6933(15) 0.021 Uiso 1 1 d D . .
H1B H 0.6523(17) 0.214(2) 0.6462(18) 0.021 Uiso 1 1 d D . .
C1 C 0.66915(16) 0.3698(3) 0.54414(16) 0.0171(5) Uani 1 1 d . . .
C2 C 0.62928(18) 0.2436(3) 0.46834(18) 0.0239(5) Uani 1 1 d . . .
H2 H 0.5973 0.1368 0.4790 0.029 Uiso 1 1 calc R . .
C3 C 0.63651(19) 0.2747(3) 0.37650(18) 0.0242(5) Uani 1 1 d . . .
H3 H 0.6098 0.1894 0.3235 0.029 Uiso 1 1 calc R . .
C4 C 0.68286(17) 0.4307(3) 0.36301(17) 0.0200(5) Uani 1 1 d . . .
C5 C 0.72181(18) 0.5585(3) 0.43820(18) 0.0241(5) Uani 1 1 d . . .
H5 H 0.7530 0.6659 0.4271 0.029 Uiso 1 1 calc R . .
C6 C 0.71458(18) 0.5274(3) 0.53029(17) 0.0225(5) Uani 1 1 d . . .
H6 H 0.7406 0.6134 0.5830 0.027 Uiso 1 1 calc R . .
C7 C 0.57075(17) 0.4357(3) 0.65014(17) 0.0188(5) Uani 1 1 d . . .
H7A H 0.5827 0.5680 0.6510 0.023 Uiso 1 1 calc R . .
H7B H 0.5074 0.4077 0.5917 0.023 Uiso 1 1 calc R . .
C8 C 0.55853(16) 0.3804(3) 0.74490(17) 0.0183(5) Uani 1 1 d . . .
C9 C 0.50711(17) 0.2223(3) 0.74927(17) 0.0205(5) Uani 1 1 d . . .
C10 C 0.49906(18) 0.1631(3) 0.83612(19) 0.0247(6) Uani 1 1 d . . .
C11 C 0.54157(18) 0.2641(4) 0.92224(18) 0.0260(6) Uani 1 1 d . . .
C12 C 0.59065(18) 0.4242(3) 0.92067(17) 0.0249(6) Uani 1 1 d . . .
C13 C 0.59845(17) 0.4809(3) 0.83286(17) 0.0199(5) Uani 1 1 d . . .
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
Br1 0.03127(14) 0.03027(14) 0.01894(13) 0.00369(11) 0.01384(10) 0.00302(11)
Cl1 0.0263(3) 0.0180(3) 0.0227(3) 0.0036(2) 0.0040(3) -0.0012(2)
F1 0.0307(8) 0.0246(7) 0.0235(8) -0.0030(6) 0.0076(6) -0.0069(6)
F2 0.0394(9) 0.0320(9) 0.0381(9) 0.0089(7) 0.0163(7) -0.0118(7)
F3 0.0480(10) 0.0487(10) 0.0244(8) 0.0126(7) 0.0196(7) -0.0018(8)
F4 0.0458(9) 0.0425(9) 0.0181(7) -0.0065(7) 0.0122(7) -0.0051(7)
F5 0.0327(8) 0.0211(7) 0.0266(8) -0.0027(6) 0.0124(6) -0.0072(6)
N1 0.0219(10) 0.0161(10) 0.0139(10) 0.0012(8) 0.0056(8) 0.0003(8)
C1 0.0163(11) 0.0195(12) 0.0145(12) 0.0019(9) 0.0048(9) 0.0028(9)
C2 0.0311(14) 0.0192(12) 0.0224(13) 0.0005(10) 0.0112(11) -0.0063(10)
C3 0.0340(14) 0.0186(12) 0.0189(12) -0.0040(10) 0.0088(11) -0.0022(10)
C4 0.0209(12) 0.0257(13) 0.0143(11) 0.0044(10) 0.0079(10) 0.0040(10)
C5 0.0261(13) 0.0233(13) 0.0241(13) 0.0004(11) 0.0109(11) -0.0067(10)
C6 0.0259(12) 0.0232(12) 0.0173(12) -0.0021(10) 0.0071(10) -0.0052(10)
C7 0.0207(12) 0.0182(12) 0.0182(12) 0.0041(10) 0.0082(10) 0.0033(9)
C8 0.0173(11) 0.0195(12) 0.0184(12) 0.0033(10) 0.0072(10) 0.0023(9)
C9 0.0199(12) 0.0217(12) 0.0187(12) -0.0004(10) 0.0061(10) 0.0003(10)
C10 0.0215(12) 0.0244(13) 0.0296(14) 0.0087(11) 0.0114(11) -0.0033(10)
C11 0.0270(14) 0.0334(14) 0.0206(13) 0.0109(11) 0.0124(11) 0.0031(11)
C12 0.0260(13) 0.0318(14) 0.0163(12) -0.0009(11) 0.0075(11) 0.0028(11)
C13 0.0185(11) 0.0191(12) 0.0222(12) 0.0012(10) 0.0081(10) 0.0015(10)
_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
Br1 C4 1.902(2) . ?
F1 C9 1.344(3) . ?
F2 C10 1.341(3) . ?
F3 C11 1.337(3) . ?
F4 C12 1.341(3) . ?
F5 C13 1.339(3) . ?
N1 C1 1.467(3) . ?
N1 C7 1.514(3) . ?
N1 H1A 0.904(16) . ?
N1 H1B 0.915(16) . ?
C1 C6 1.380(3) . ?
C1 C2 1.382(3) . ?
C2 C3 1.387(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.375(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(3) . ?
C5 C6 1.390(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.499(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.389(3) . ?
C8 C13 1.389(3) . ?
C9 C10 1.372(3) . ?
C10 C11 1.374(4) . ?
C11 C12 1.375(4) . ?
C12 C13 1.378(3) . ?
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 C7 112.63(17) . . ?
C1 N1 H1A 112.3(16) . . ?
C7 N1 H1A 107.8(16) . . ?
C1 N1 H1B 108.1(15) . . ?
C7 N1 H1B 110.0(15) . . ?
H1A N1 H1B 106(2) . . ?
C6 C1 C2 121.7(2) . . ?
C6 C1 N1 119.8(2) . . ?
C2 C1 N1 118.4(2) . . ?
C1 C2 C3 119.1(2) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C4 C3 C2 119.2(2) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 121.9(2) . . ?
C3 C4 Br1 118.57(18) . . ?
C5 C4 Br1 119.49(17) . . ?
C4 C5 C6 118.9(2) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C1 C6 C5 119.1(2) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C8 C7 N1 110.07(17) . . ?
C8 C7 H7A 109.6 . . ?
N1 C7 H7A 109.6 . . ?
C8 C7 H7B 109.6 . . ?
N1 C7 H7B 109.6 . . ?
H7A C7 H7B 108.2 . . ?
C9 C8 C13 116.4(2) . . ?
C9 C8 C7 121.0(2) . . ?
C13 C8 C7 122.6(2) . . ?
F1 C9 C10 118.6(2) . . ?
F1 C9 C8 118.9(2) . . ?
C10 C9 C8 122.5(2) . . ?
F2 C10 C9 120.2(2) . . ?
F2 C10 C11 120.3(2) . . ?
C9 C10 C11 119.5(2) . . ?
F3 C11 C10 120.2(2) . . ?
F3 C11 C12 119.8(2) . . ?
C10 C11 C12 120.0(2) . . ?
F4 C12 C11 120.0(2) . . ?
F4 C12 C13 120.3(2) . . ?
C11 C12 C13 119.7(2) . . ?
F5 C13 C12 118.0(2) . . ?
F5 C13 C8 120.0(2) . . ?
C12 C13 C8 122.0(2) . . ?
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
C7 N1 C1 C6 80.1(3) . . . . ?
C7 N1 C1 C2 -98.2(2) . . . . ?
C6 C1 C2 C3 1.0(4) . . . . ?
N1 C1 C2 C3 179.3(2) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
C2 C3 C4 Br1 -178.95(18) . . . . ?
C3 C4 C5 C6 0.6(4) . . . . ?
Br1 C4 C5 C6 178.93(17) . . . . ?
C2 C1 C6 C5 -1.0(3) . . . . ?
N1 C1 C6 C5 -179.3(2) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
C1 N1 C7 C8 174.04(18) . . . . ?
N1 C7 C8 C9 -82.1(3) . . . . ?
N1 C7 C8 C13 97.0(2) . . . . ?
C13 C8 C9 F1 175.05(19) . . . . ?
C7 C8 C9 F1 -5.8(3) . . . . ?
C13 C8 C9 C10 -2.5(3) . . . . ?
C7 C8 C9 C10 176.6(2) . . . . ?
F1 C9 C10 F2 3.3(3) . . . . ?
C8 C9 C10 F2 -179.1(2) . . . . ?
F1 C9 C10 C11 -176.4(2) . . . . ?
C8 C9 C10 C11 1.2(4) . . . . ?
F2 C10 C11 F3 -0.3(4) . . . . ?
C9 C10 C11 F3 179.4(2) . . . . ?
F2 C10 C11 C12 -179.0(2) . . . . ?
C9 C10 C11 C12 0.7(4) . . . . ?
F3 C11 C12 F4 0.2(3) . . . . ?
C10 C11 C12 F4 178.9(2) . . . . ?
F3 C11 C12 C13 -179.8(2) . . . . ?
C10 C11 C12 C13 -1.1(4) . . . . ?
F4 C12 C13 F5 -2.1(3) . . . . ?
C11 C12 C13 F5 178.0(2) . . . . ?
F4 C12 C13 C8 179.6(2) . . . . ?
C11 C12 C13 C8 -0.4(4) . . . . ?
C9 C8 C13 F5 -176.19(19) . . . . ?
C7 C8 C13 F5 4.7(3) . . . . ?
C9 C8 C13 C12 2.1(3) . . . . ?
C7 C8 C13 C12 -177.0(2) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1B Cl1 0.915(16) 2.188(17) 3.096(2) 172(2) .
N1 H1A Cl1 0.904(16) 2.172(17) 3.068(2) 171(2) 2_656
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max 0.303
_refine_diff_density_min -0.255
_refine_diff_density_rms 0.059
# Attachment 'Comp4.cif'
data_mm-82-7
_database_code_depnum_ccdc_archive 'CCDC 745351'
#TrackingRef 'Comp4.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C13 H8 Br F5 N, Br'
_chemical_formula_sum 'C13 H8 Br2 F5 N'
_chemical_formula_weight 433.02
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_H-M Pca21
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'
_cell_length_a 7.77800(10)
_cell_length_b 24.2111(5)
_cell_length_c 7.79200(10)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 1467.34(4)
_cell_formula_units_Z 4
_cell_measurement_temperature 123.0(1)
_cell_measurement_reflns_used 2144
_cell_measurement_theta_max 28.283
_cell_measurement_theta_min 0.407
_exptl_crystal_description plate
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.20
_exptl_crystal_size_mid 0.16
_exptl_crystal_size_min 0.08
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.960
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 832
_exptl_absorpt_coefficient_mu 5.570
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.3860
_exptl_absorpt_correction_T_max 0.6376
_exptl_absorpt_process_details 'Sadabs (Sheldrick, 1996)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 123.0(1)
_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 Kappa APEX-II'
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 15140
_diffrn_reflns_av_R_equivalents 0.0720
_diffrn_reflns_av_sigmaI/netI 0.0554
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_k_min -28
_diffrn_reflns_limit_k_max 28
_diffrn_reflns_limit_l_min -9
_diffrn_reflns_limit_l_max 9
_diffrn_reflns_theta_min 2.52
_diffrn_reflns_theta_max 25.01
_reflns_number_total 2584
_reflns_number_gt 2319
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'Collect (Bruker, 2004)'
_computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution 'SIR-2002 (Burla, et al., 2003)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
'SHELXL-97; MERCURY (Macrae, et al., 2006)'
_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^)+(0.0000P)^2^+2.9818P] 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 mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.120(13)
_refine_ls_number_reflns 2584
_refine_ls_number_parameters 197
_refine_ls_number_restraints 3
_refine_ls_R_factor_all 0.0419
_refine_ls_R_factor_gt 0.0352
_refine_ls_wR_factor_ref 0.0691
_refine_ls_wR_factor_gt 0.0669
_refine_ls_goodness_of_fit_ref 1.035
_refine_ls_restrained_S_all 1.035
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
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
Br1 Br 0.40314(7) 0.492604(19) 0.71817(9) 0.02690(15) Uani 1 1 d . . .
Br2 Br 0.96510(6) 0.74330(2) 0.79256(8) 0.02420(14) Uani 1 1 d . . .
F1 F 0.2684(5) 0.82645(12) 1.0328(4) 0.0274(8) Uani 1 1 d . . .
F2 F 0.3076(4) 0.93279(12) 1.1235(5) 0.0337(8) Uani 1 1 d . . .
F3 F 0.5399(4) 0.99749(12) 0.9547(5) 0.0308(9) Uani 1 1 d . . .
F4 F 0.7391(4) 0.95333(11) 0.7052(5) 0.0350(8) Uani 1 1 d . . .
F5 F 0.6978(4) 0.84684(13) 0.6116(5) 0.0291(8) Uani 1 1 d . . .
N1 N 0.5588(5) 0.73411(17) 0.8745(6) 0.0139(9) Uani 1 1 d D . .
H1A H 0.541(7) 0.740(2) 0.988(3) 0.017 Uiso 1 1 d D . .
H1B H 0.670(3) 0.7379(19) 0.842(6) 0.017 Uiso 1 1 d D . .
C1 C 0.5183(6) 0.6758(2) 0.8357(6) 0.0131(12) Uani 1 1 d . . .
C2 C 0.4066(7) 0.6473(2) 0.9409(8) 0.0252(13) Uani 1 1 d . . .
H2 H 0.3548 0.6650 1.0365 0.030 Uiso 1 1 calc R . .
C3 C 0.3711(7) 0.5927(2) 0.9055(8) 0.0254(14) Uani 1 1 d . . .
H3 H 0.2963 0.5721 0.9775 0.030 Uiso 1 1 calc R . .
C4 C 0.4465(6) 0.56835(19) 0.7630(7) 0.0187(14) Uani 1 1 d . . .
C5 C 0.5541(7) 0.5972(2) 0.6564(7) 0.0235(13) Uani 1 1 d . . .
H5 H 0.6030 0.5799 0.5586 0.028 Uiso 1 1 calc R . .
C6 C 0.5909(7) 0.6520(2) 0.6929(7) 0.0186(12) Uani 1 1 d . . .
H6 H 0.6650 0.6727 0.6204 0.022 Uiso 1 1 calc R . .
C7 C 0.4539(6) 0.77375(19) 0.7687(7) 0.0145(12) Uani 1 1 d . . .
H7A H 0.3304 0.7648 0.7820 0.017 Uiso 1 1 calc R . .
H7B H 0.4842 0.7692 0.6461 0.017 Uiso 1 1 calc R . .
C8 C 0.4834(6) 0.8332(2) 0.8209(7) 0.0149(13) Uani 1 1 d . . .
C9 C 0.3860(6) 0.8574(2) 0.9504(7) 0.0164(12) Uani 1 1 d . . .
C10 C 0.4041(7) 0.9117(2) 0.9968(8) 0.0241(13) Uani 1 1 d . . .
C11 C 0.5209(7) 0.9444(2) 0.9134(7) 0.0215(13) Uani 1 1 d . . .
C12 C 0.6219(6) 0.9221(2) 0.7849(8) 0.0214(12) Uani 1 1 d . . .
C13 C 0.6014(6) 0.8668(2) 0.7427(7) 0.0170(12) Uani 1 1 d . . .
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
Br1 0.0280(3) 0.0163(2) 0.0363(3) -0.0008(3) -0.0031(3) -0.0034(2)
Br2 0.0159(2) 0.0404(3) 0.0163(2) -0.0027(3) 0.0008(3) -0.0046(2)
F1 0.0273(18) 0.0233(16) 0.032(2) -0.0014(15) 0.0123(15) -0.0034(16)
F2 0.041(2) 0.0270(18) 0.033(2) -0.0069(17) 0.0136(17) 0.0049(16)
F3 0.037(2) 0.0131(17) 0.042(2) 0.0002(15) -0.0056(19) -0.0004(15)
F4 0.0341(18) 0.0232(16) 0.048(2) 0.0089(19) 0.0117(19) -0.0082(13)
F5 0.031(2) 0.0264(17) 0.030(2) 0.0018(16) 0.0141(15) -0.0022(14)
N1 0.012(2) 0.017(2) 0.013(2) -0.003(2) 0.0039(19) 0.0023(18)
C1 0.014(3) 0.013(3) 0.012(4) -0.001(2) -0.003(2) -0.001(2)
C2 0.023(3) 0.029(3) 0.023(3) 0.000(3) 0.010(3) 0.004(3)
C3 0.022(3) 0.020(3) 0.033(4) 0.000(3) 0.004(3) 0.001(2)
C4 0.019(3) 0.014(2) 0.023(4) 0.001(2) -0.002(2) 0.001(2)
C5 0.031(3) 0.022(3) 0.018(3) -0.004(2) -0.001(3) 0.003(2)
C6 0.019(3) 0.020(3) 0.017(3) 0.009(3) 0.006(3) -0.002(2)
C7 0.014(2) 0.022(3) 0.008(3) 0.004(2) -0.001(2) -0.005(2)
C8 0.011(3) 0.020(3) 0.013(4) -0.002(2) 0.000(2) -0.001(2)
C9 0.010(3) 0.018(3) 0.022(3) 0.005(2) 0.002(2) -0.002(2)
C10 0.025(3) 0.024(3) 0.023(3) 0.001(3) 0.001(3) 0.004(3)
C11 0.025(3) 0.014(3) 0.025(4) -0.001(2) -0.005(3) -0.003(2)
C12 0.015(3) 0.020(3) 0.029(3) 0.006(3) 0.001(3) -0.005(2)
C13 0.018(3) 0.020(3) 0.012(3) 0.000(2) 0.003(2) 0.003(2)
_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
Br1 C4 1.897(5) . ?
F1 C9 1.345(6) . ?
F2 C10 1.341(7) . ?
F3 C11 1.332(6) . ?
F4 C12 1.337(6) . ?
F5 C13 1.356(6) . ?
N1 C1 1.478(6) . ?
N1 C7 1.505(6) . ?
N1 H1A 0.91(2) . ?
N1 H1B 0.908(19) . ?
C1 C6 1.375(7) . ?
C1 C2 1.380(7) . ?
C2 C3 1.377(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.371(8) . ?
C5 C6 1.385(7) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.513(7) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C13 1.369(7) . ?
C8 C9 1.392(7) . ?
C9 C10 1.371(8) . ?
C10 C11 1.369(8) . ?
C11 C12 1.383(8) . ?
C12 C13 1.389(7) . ?
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 C7 112.4(4) . . ?
C1 N1 H1A 109(3) . . ?
C7 N1 H1A 110(3) . . ?
C1 N1 H1B 104(3) . . ?
C7 N1 H1B 107(3) . . ?
H1A N1 H1B 114(5) . . ?
C6 C1 C2 122.0(5) . . ?
C6 C1 N1 118.6(4) . . ?
C2 C1 N1 119.4(5) . . ?
C3 C2 C1 119.2(5) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 118.9(5) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 121.7(5) . . ?
C5 C4 Br1 119.4(4) . . ?
C3 C4 Br1 118.9(4) . . ?
C4 C5 C6 119.3(5) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C1 C6 C5 118.9(5) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
N1 C7 C8 112.2(4) . . ?
N1 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
N1 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C13 C8 C9 115.9(5) . . ?
C13 C8 C7 123.2(5) . . ?
C9 C8 C7 120.9(5) . . ?
F1 C9 C10 118.6(5) . . ?
F1 C9 C8 118.8(4) . . ?
C10 C9 C8 122.6(5) . . ?
F2 C10 C11 120.1(5) . . ?
F2 C10 C9 120.1(5) . . ?
C11 C10 C9 119.9(5) . . ?
F3 C11 C10 121.1(5) . . ?
F3 C11 C12 119.3(5) . . ?
C10 C11 C12 119.6(5) . . ?
F4 C12 C11 120.1(5) . . ?
F4 C12 C13 120.9(5) . . ?
C11 C12 C13 118.9(5) . . ?
F5 C13 C8 119.6(4) . . ?
F5 C13 C12 117.3(5) . . ?
C8 C13 C12 123.0(5) . . ?
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
C7 N1 C1 C6 80.4(6) . . . . ?
C7 N1 C1 C2 -98.2(6) . . . . ?
C6 C1 C2 C3 2.3(8) . . . . ?
N1 C1 C2 C3 -179.1(5) . . . . ?
C1 C2 C3 C4 -1.2(8) . . . . ?
C2 C3 C4 C5 -0.4(8) . . . . ?
C2 C3 C4 Br1 178.1(4) . . . . ?
C3 C4 C5 C6 0.9(8) . . . . ?
Br1 C4 C5 C6 -177.6(4) . . . . ?
C2 C1 C6 C5 -1.8(8) . . . . ?
N1 C1 C6 C5 179.6(5) . . . . ?
C4 C5 C6 C1 0.1(8) . . . . ?
C1 N1 C7 C8 174.5(4) . . . . ?
N1 C7 C8 C13 93.9(6) . . . . ?
N1 C7 C8 C9 -88.1(6) . . . . ?
C13 C8 C9 F1 -179.7(5) . . . . ?
C7 C8 C9 F1 2.2(7) . . . . ?
C13 C8 C9 C10 0.8(8) . . . . ?
C7 C8 C9 C10 -177.4(5) . . . . ?
F1 C9 C10 F2 0.9(8) . . . . ?
C8 C9 C10 F2 -179.5(5) . . . . ?
F1 C9 C10 C11 -179.0(5) . . . . ?
C8 C9 C10 C11 0.5(9) . . . . ?
F2 C10 C11 F3 -0.7(8) . . . . ?
C9 C10 C11 F3 179.3(5) . . . . ?
F2 C10 C11 C12 178.9(5) . . . . ?
C9 C10 C11 C12 -1.1(8) . . . . ?
F3 C11 C12 F4 1.1(8) . . . . ?
C10 C11 C12 F4 -178.5(5) . . . . ?
F3 C11 C12 C13 180.0(5) . . . . ?
C10 C11 C12 C13 0.4(8) . . . . ?
C9 C8 C13 F5 -178.0(5) . . . . ?
C7 C8 C13 F5 0.1(8) . . . . ?
C9 C8 C13 C12 -1.6(8) . . . . ?
C7 C8 C13 C12 176.6(5) . . . . ?
F4 C12 C13 F5 -3.6(8) . . . . ?
C11 C12 C13 F5 177.5(5) . . . . ?
F4 C12 C13 C8 179.9(5) . . . . ?
C11 C12 C13 C8 1.0(8) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A Br2 0.91(2) 2.38(2) 3.271(5) 169(5) 3_655
N1 H1B Br2 0.908(19) 2.33(2) 3.232(4) 173(5) .
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 25.01
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max 0.544
_refine_diff_density_min -0.443
_refine_diff_density_rms 0.095
# Attachment 'Comp2.cif'
data_mm-080-2
_database_code_depnum_ccdc_archive 'CCDC 775333'
#TrackingRef 'Comp2.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C13 H9 F5 N, Cl '
_chemical_formula_sum 'C13 H9 Cl F5 N'
_chemical_formula_weight 309.66
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M Pc
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
_cell_length_a 11.7935(6)
_cell_length_b 7.5988(3)
_cell_length_c 7.5838(3)
_cell_angle_alpha 90.00
_cell_angle_beta 103.138(3)
_cell_angle_gamma 90.00
_cell_volume 661.84(5)
_cell_formula_units_Z 2
_cell_measurement_temperature 123(2)
_cell_measurement_reflns_used 1700
_cell_measurement_theta_max 28.283
_cell_measurement_theta_min 0.407
_exptl_crystal_description plate
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.30
_exptl_crystal_size_mid 0.25
_exptl_crystal_size_min 0.10
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.554
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 312
_exptl_absorpt_coefficient_mu 0.335
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9060
_exptl_absorpt_correction_T_max 0.9672
_exptl_absorpt_process_details Sadabs
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 123(2)
_diffrn_radiation_wavelength 0.71069
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 8080
_diffrn_reflns_av_R_equivalents 0.0487
_diffrn_reflns_av_sigmaI/netI 0.0484
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 14
_diffrn_reflns_limit_k_min -9
_diffrn_reflns_limit_k_max 9
_diffrn_reflns_limit_l_min -9
_diffrn_reflns_limit_l_max 8
_diffrn_reflns_theta_min 3.21
_diffrn_reflns_theta_max 25.01
_reflns_number_total 2067
_reflns_number_gt 1918
_reflns_threshold_expression >2\s(I)
_computing_data_collection 'Collect (Bruker, 2008)'
_computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction DENZO-SMN
_computing_structure_solution 'SIR-2004 (Burla, et al., 2005)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997); MERCURY (Macrae, et al., 2006)'
_computing_publication_material SHELXL-97
_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^ > 2\s(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^)+(0.0098P)^2^+0.4492P] 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 constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.11(7)
_refine_ls_number_reflns 2067
_refine_ls_number_parameters 181
_refine_ls_number_restraints 2
_refine_ls_R_factor_all 0.0404
_refine_ls_R_factor_gt 0.0356
_refine_ls_wR_factor_ref 0.0763
_refine_ls_wR_factor_gt 0.0746
_refine_ls_goodness_of_fit_ref 1.042
_refine_ls_restrained_S_all 1.042
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
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
Cl1 Cl 0.60191(8) 0.21379(9) 0.45511(10) 0.0285(2) Uani 1 1 d . . .
F9 F 0.40371(17) 0.0526(2) 1.0823(2) 0.0321(5) Uani 1 1 d . . .
F10 F 0.17620(18) 0.0229(3) 0.9269(3) 0.0395(5) Uani 1 1 d . . .
F11 F 0.07999(16) 0.2224(3) 0.6344(2) 0.0323(5) Uani 1 1 d . . .
F12 F 0.21495(18) 0.4469(3) 0.4931(3) 0.0374(5) Uani 1 1 d . . .
F13 F 0.44315(17) 0.4783(2) 0.6500(3) 0.0311(5) Uani 1 1 d . . .
N1 N 0.6365(2) 0.1781(3) 0.8707(3) 0.0179(5) Uani 1 1 d . . .
H1A H 0.6221 0.0611 0.8880 0.022 Uiso 1 1 calc R . .
H1B H 0.6203 0.1991 0.7480 0.022 Uiso 1 1 calc R . .
C1 C 0.7604(3) 0.2166(4) 0.9489(4) 0.0208(7) Uani 1 1 d . . .
C2 C 0.8183(3) 0.1242(5) 1.0967(5) 0.0369(9) Uani 1 1 d . . .
H2 H 0.7795 0.0343 1.1470 0.044 Uiso 1 1 calc R . .
C3 C 0.9334(3) 0.1622(5) 1.1723(6) 0.0441(10) Uani 1 1 d . . .
H3 H 0.9739 0.0983 1.2751 0.053 Uiso 1 1 calc R . .
C4 C 0.9895(3) 0.2913(6) 1.1001(5) 0.0400(9) Uani 1 1 d . . .
H4 H 1.0686 0.3176 1.1529 0.048 Uiso 1 1 calc R . .
C5 C 0.9311(3) 0.3828(6) 0.9509(5) 0.0492(11) Uani 1 1 d . . .
H5 H 0.9706 0.4714 0.8997 0.059 Uiso 1 1 calc R . .
C6 C 0.8145(3) 0.3470(5) 0.8738(5) 0.0404(9) Uani 1 1 d . . .
H6 H 0.7736 0.4114 0.7717 0.048 Uiso 1 1 calc R . .
C7 C 0.5583(3) 0.2895(4) 0.9562(4) 0.0203(7) Uani 1 1 d . . .
H7A H 0.5785 0.4150 0.9465 0.024 Uiso 1 1 calc R . .
H7B H 0.5716 0.2598 1.0864 0.024 Uiso 1 1 calc R . .
C8 C 0.4318(3) 0.2627(4) 0.8679(4) 0.0175(6) Uani 1 1 d . . .
C9 C 0.3603(3) 0.1496(4) 0.9354(4) 0.0197(7) Uani 1 1 d . . .
C10 C 0.2429(3) 0.1345(4) 0.8584(4) 0.0244(7) Uani 1 1 d . . .
C11 C 0.1941(3) 0.2349(4) 0.7102(5) 0.0233(7) Uani 1 1 d . . .
C12 C 0.2631(3) 0.3485(4) 0.6392(4) 0.0245(7) Uani 1 1 d . . .
C13 C 0.3785(3) 0.3618(4) 0.7186(4) 0.0199(7) Uani 1 1 d . . .
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
Cl1 0.0476(5) 0.0184(3) 0.0180(3) 0.0005(3) 0.0042(3) 0.0044(4)
F9 0.0295(11) 0.0361(11) 0.0279(11) 0.0158(8) 0.0007(9) -0.0042(9)
F10 0.0263(12) 0.0459(13) 0.0450(14) 0.0172(10) 0.0050(10) -0.0124(9)
F11 0.0207(10) 0.0387(11) 0.0351(11) 0.0015(9) 0.0017(9) 0.0001(9)
F12 0.0331(12) 0.0415(13) 0.0340(12) 0.0194(9) 0.0000(10) 0.0050(9)
F13 0.0306(12) 0.0280(11) 0.0340(11) 0.0142(9) 0.0057(9) -0.0055(9)
N1 0.0220(14) 0.0140(12) 0.0174(12) -0.0006(10) 0.0036(11) -0.0009(10)
C1 0.0172(16) 0.0227(16) 0.0228(17) -0.0043(13) 0.0051(14) 0.0002(13)
C2 0.028(2) 0.0342(19) 0.043(2) 0.0122(17) -0.0048(16) -0.0025(16)
C3 0.031(2) 0.043(2) 0.048(2) 0.0048(18) -0.0120(19) 0.0018(18)
C4 0.0190(18) 0.052(2) 0.047(2) -0.0119(19) 0.0037(17) -0.0044(17)
C5 0.036(2) 0.064(3) 0.045(2) 0.009(2) 0.0043(19) -0.027(2)
C6 0.036(2) 0.051(2) 0.0282(18) 0.0126(17) -0.0047(16) -0.0130(17)
C7 0.0191(16) 0.0192(15) 0.0219(15) -0.0059(13) 0.0032(14) 0.0000(13)
C8 0.0214(16) 0.0166(15) 0.0153(15) -0.0015(13) 0.0061(13) -0.0006(13)
C9 0.0236(17) 0.0211(16) 0.0135(15) 0.0017(12) 0.0026(13) 0.0047(13)
C10 0.0284(19) 0.0210(16) 0.0243(17) 0.0018(14) 0.0071(14) -0.0057(14)
C11 0.0167(17) 0.0249(17) 0.0252(16) -0.0068(15) -0.0016(13) 0.0029(14)
C12 0.0278(19) 0.0210(17) 0.0217(16) 0.0051(13) -0.0005(14) 0.0030(14)
C13 0.0238(18) 0.0138(14) 0.0230(16) 0.0003(12) 0.0073(14) 0.0023(13)
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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
F9 C9 1.337(3) . ?
F10 C10 1.339(4) . ?
F11 C11 1.341(4) . ?
F12 C12 1.350(4) . ?
F13 C13 1.348(4) . ?
N1 C1 1.475(4) . ?
N1 C7 1.503(4) . ?
N1 H1A 0.9200 . ?
N1 H1B 0.9200 . ?
C1 C2 1.366(4) . ?
C1 C6 1.371(5) . ?
C2 C3 1.379(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.365(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.372(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.393(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.504(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.381(4) . ?
C8 C13 1.386(4) . ?
C9 C10 1.379(5) . ?
C10 C11 1.372(5) . ?
C11 C12 1.376(5) . ?
C12 C13 1.362(5) . ?
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 C7 111.3(2) . . ?
C1 N1 H1A 109.4 . . ?
C7 N1 H1A 109.4 . . ?
C1 N1 H1B 109.4 . . ?
C7 N1 H1B 109.4 . . ?
H1A N1 H1B 108.0 . . ?
C2 C1 C6 121.2(3) . . ?
C2 C1 N1 119.6(3) . . ?
C6 C1 N1 119.2(3) . . ?
C1 C2 C3 119.7(3) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 120.3(4) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 119.8(3) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 120.6(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 118.4(3) . . ?
C1 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
N1 C7 C8 112.1(2) . . ?
N1 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
N1 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C9 C8 C13 116.1(3) . . ?
C9 C8 C7 123.2(3) . . ?
C13 C8 C7 120.6(3) . . ?
F9 C9 C10 117.7(3) . . ?
F9 C9 C8 120.1(3) . . ?
C10 C9 C8 122.2(3) . . ?
F10 C10 C11 119.8(3) . . ?
F10 C10 C9 120.6(3) . . ?
C11 C10 C9 119.6(3) . . ?
F11 C11 C10 120.3(3) . . ?
F11 C11 C12 120.1(3) . . ?
C10 C11 C12 119.6(3) . . ?
F12 C12 C13 120.9(3) . . ?
F12 C12 C11 119.5(3) . . ?
C13 C12 C11 119.6(3) . . ?
F13 C13 C12 118.3(3) . . ?
F13 C13 C8 118.8(3) . . ?
C12 C13 C8 122.9(3) . . ?
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
C7 N1 C1 C2 89.8(3) . . . . ?
C7 N1 C1 C6 -88.9(4) . . . . ?
C6 C1 C2 C3 0.0(5) . . . . ?
N1 C1 C2 C3 -178.7(3) . . . . ?
C1 C2 C3 C4 -0.1(6) . . . . ?
C2 C3 C4 C5 -0.4(7) . . . . ?
C3 C4 C5 C6 0.9(7) . . . . ?
C2 C1 C6 C5 0.5(6) . . . . ?
N1 C1 C6 C5 179.3(3) . . . . ?
C4 C5 C6 C1 -1.0(7) . . . . ?
C1 N1 C7 C8 175.4(2) . . . . ?
N1 C7 C8 C9 96.7(3) . . . . ?
N1 C7 C8 C13 -87.9(3) . . . . ?
C13 C8 C9 F9 -178.1(3) . . . . ?
C7 C8 C9 F9 -2.5(5) . . . . ?
C13 C8 C9 C10 0.5(4) . . . . ?
C7 C8 C9 C10 176.1(3) . . . . ?
F9 C9 C10 F10 -1.6(4) . . . . ?
C8 C9 C10 F10 179.7(3) . . . . ?
F9 C9 C10 C11 178.4(3) . . . . ?
C8 C9 C10 C11 -0.3(5) . . . . ?
F10 C10 C11 F11 0.4(5) . . . . ?
C9 C10 C11 F11 -179.7(3) . . . . ?
F10 C10 C11 C12 -179.5(3) . . . . ?
C9 C10 C11 C12 0.5(5) . . . . ?
F11 C11 C12 F12 0.0(5) . . . . ?
C10 C11 C12 F12 179.9(3) . . . . ?
F11 C11 C12 C13 179.2(3) . . . . ?
C10 C11 C12 C13 -1.0(5) . . . . ?
F12 C12 C13 F13 1.4(5) . . . . ?
C11 C12 C13 F13 -177.8(3) . . . . ?
F12 C12 C13 C8 -179.6(3) . . . . ?
C11 C12 C13 C8 1.3(5) . . . . ?
C9 C8 C13 F13 178.0(3) . . . . ?
C7 C8 C13 F13 2.3(4) . . . . ?
C9 C8 C13 C12 -1.0(4) . . . . ?
C7 C8 C13 C12 -176.8(3) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A Cl1 0.92 2.18 3.093(2) 174.0 2
N1 H1B Cl1 0.92 2.19 3.096(2) 170.6 .
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 25.01
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max 0.206
_refine_diff_density_min -0.207
_refine_diff_density_rms 0.047