#------------------------------------------------------------------------------
#$Date: 2015-05-13 11:33:30 +0300 (Wed, 13 May 2015) $
#$Revision: 136163 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/71/7117163.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_7117163
loop_
_publ_author_name
'Fanny Frausto'
'Zachary C. Smith'
'Terry E. Haas'
'Samuel W. Thomas III'
_publ_section_title
;
 Two-dimensional bricklayer arrangements of tolans using halogen bonding
 interactions
;
_journal_name_full               Chem.Commun.
_journal_page_first              8825
_journal_paper_doi               10.1039/C5cc02225H
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C15 H9 N'
_chemical_formula_weight         203.23
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2015-03-16 deposited with the CCDC.
2015-04-29 downloaded from the CCDC.
;
_cell_angle_alpha                94.412(6)
_cell_angle_beta                 102.356(6)
_cell_angle_gamma                103.038(6)
_cell_formula_units_Z            4
_cell_length_a                   9.404(3)
_cell_length_b                   9.480(3)
_cell_length_c                   13.047(4)
_cell_measurement_temperature    100(2)
_cell_volume                     1097.3(6)
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'omega, phi scans'
_diffrn_radiation_monochromator  Triumph
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_av_unetI/netI     0.0659
_diffrn_reflns_laue_measured_fraction_full 0.993
_diffrn_reflns_laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15077
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.490
_diffrn_reflns_theta_min         2.767
_diffrn_source                   'Mo sealed tube'
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.9820
_exptl_absorpt_correction_T_min  0.9310
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_description       prism
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.176
_exptl_crystal_size_min          0.102
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4487
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.1216
_refine_ls_R_factor_gt           0.0641
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1090P)²+0.1842P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1753
_refine_ls_wR_factor_ref         0.2104
_reflns_Friedel_coverage         0.000
_reflns_friedel_fraction_full    .
_reflns_friedel_fraction_max     .
_reflns_number_gt                2527
_reflns_number_total             4487
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cc02225h2.cif
_cod_data_source_block           FF1128_P-1_a
_cod_database_code               7117163
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.931
_shelx_estimated_absorpt_t_max   0.982
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N001 N 0.2629(3) 0.3262(2) 0.51660(18) 0.0401(6) Uani 1 1 d . . . . .
C002 C 0.8771(3) 0.3545(3) 0.12242(19) 0.0244(6) Uani 1 1 d . . . . .
N003 N 1.2020(3) 0.6749(3) 0.48918(19) 0.0444(7) Uani 1 1 d . . . . .
C004 C 0.6192(3) 0.6429(2) 0.87383(19) 0.0258(6) Uani 1 1 d . . . . .
C005 C 0.8812(3) 0.8801(2) 1.14780(19) 0.0250(6) Uani 1 1 d . . . . .
C006 C 1.0320(3) 0.9472(3) 1.1563(2) 0.0269(6) Uani 1 1 d . . . . .
H006 H 1.0717 0.9473 1.0952 0.032 Uiso 1 1 calc R U . . .
C007 C 0.4339(3) 0.4835(2) 0.68719(18) 0.0248(6) Uani 1 1 d . . . . .
C008 C 0.7886(3) 0.8019(3) 1.0498(2) 0.0259(6) Uani 1 1 d . . . . .
C009 C 1.0450(3) 0.5180(3) 0.31351(19) 0.0263(6) Uani 1 1 d . . . . .
C00A C 0.7847(3) 0.2731(3) 0.0258(2) 0.0269(6) Uani 1 1 d . . . . .
C00B C 0.6100(3) 0.1288(2) -0.15395(19) 0.0249(6) Uani 1 1 d . . . . .
C00C C 0.7128(3) 0.7290(3) 0.9691(2) 0.0273(6) Uani 1 1 d . . . . .
C00D C 0.6021(3) 0.1972(3) -0.24516(19) 0.0267(6) Uani 1 1 d . . . . .
H00D H 0.6524 0.2972 -0.2402 0.032 Uiso 1 1 calc R U . . .
C00E C 0.9823(3) 0.3700(3) 0.30934(19) 0.0270(6) Uani 1 1 d . . . . .
H00E H 0.9961 0.3245 0.3718 0.032 Uiso 1 1 calc R U . . .
C00F C 0.6736(3) 0.6322(2) 0.78247(19) 0.0264(6) Uani 1 1 d . . . . .
H00F H 0.7748 0.6795 0.7846 0.032 Uiso 1 1 calc R U . . .
C00G C 0.3379(3) 0.3971(3) 0.5921(2) 0.0283(6) Uani 1 1 d . . . . .
C00H C 0.3792(3) 0.4916(3) 0.77790(19) 0.0263(6) Uani 1 1 d . . . . .
H00H H 0.2787 0.4421 0.7761 0.032 Uiso 1 1 calc R U . . .
C00I C 1.0253(3) 0.5845(3) 0.2220(2) 0.0275(6) Uani 1 1 d . . . . .
H00I H 1.0685 0.6860 0.2250 0.033 Uiso 1 1 calc R U . . .
C00J C 0.9438(3) 0.5044(3) 0.1275(2) 0.0270(6) Uani 1 1 d . . . . .
H00J H 0.9322 0.5501 0.0650 0.032 Uiso 1 1 calc R U . . .
C00K C 0.4708(3) 0.5713(3) 0.86992(19) 0.0262(6) Uani 1 1 d . . . . .
H00K H 0.4330 0.5779 0.9316 0.031 Uiso 1 1 calc R U . . .
C00L C 0.5819(3) 0.5540(3) 0.68999(19) 0.0283(6) Uani 1 1 d . . . . .
H00L H 0.6191 0.5480 0.6280 0.034 Uiso 1 1 calc R U . . .
C00M C 0.9002(3) 0.2895(3) 0.21496(19) 0.0262(6) Uani 1 1 d . . . . .
H00M H 0.8583 0.1879 0.2125 0.031 Uiso 1 1 calc R U . . .
C00N C 0.5319(3) -0.0172(3) -0.1622(2) 0.0286(6) Uani 1 1 d . . . . .
H00N H 0.5336 -0.0648 -0.1006 0.034 Uiso 1 1 calc R U . . .
C00O C 1.1312(3) 0.6046(3) 0.4112(2) 0.0309(6) Uani 1 1 d . . . . .
C00P C 0.4474(3) -0.0235(3) -0.3497(2) 0.0315(6) Uani 1 1 d . . . . .
H00P H 0.3925 -0.0759 -0.4167 0.038 Uiso 1 1 calc R U . . .
C00Q C 0.8247(3) 0.8832(3) 1.23789(19) 0.0279(6) Uani 1 1 d . . . . .
H00Q H 0.7219 0.8386 1.2330 0.034 Uiso 1 1 calc R U . . .
C00R C 0.5224(3) 0.1216(3) -0.3419(2) 0.0307(6) Uani 1 1 d . . . . .
H00R H 0.5188 0.1691 -0.4036 0.037 Uiso 1 1 calc R U . . .
C00S C 0.4525(3) -0.0921(3) -0.2597(2) 0.0313(6) Uani 1 1 d . . . . .
H00S H 0.4007 -0.1918 -0.2652 0.038 Uiso 1 1 calc R U . . .
C00T C 1.1233(3) 1.0132(3) 1.2529(2) 0.0287(6) Uani 1 1 d . . . . .
H00T H 1.2262 1.0583 1.2583 0.034 Uiso 1 1 calc R U . . .
C00U C 0.9167(3) 0.9505(3) 1.3340(2) 0.0328(6) Uani 1 1 d . . . . .
H00U H 0.8769 0.9528 1.3949 0.039 Uiso 1 1 calc R U . . .
C00V C 0.7013(3) 0.2065(3) -0.0552(2) 0.0272(6) Uani 1 1 d . . . . .
C00W C 1.0663(3) 1.0145(3) 1.3424(2) 0.0312(6) Uani 1 1 d . . . . .
H00W H 1.1300 1.0592 1.4091 0.037 Uiso 1 1 calc R U . . .
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'
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
C00M C002 C00J 118.4(2) . .
C00M C002 C00A 121.1(2) . .
C00J C002 C00A 120.5(2) . .
C00K C004 C00F 119.1(2) . .
C00K C004 C00C 120.3(2) . .
C00F C004 C00C 120.5(2) . .
C00Q C005 C006 119.0(2) . .
C00Q C005 C008 120.4(2) . .
C006 C005 C008 120.6(2) . .
C00T C006 C005 120.2(2) . .
C00T C006 H006 119.9 . .
C005 C006 H006 119.9 . .
C00H C007 C00L 120.3(2) . .
C00H C007 C00G 119.1(2) . .
C00L C007 C00G 120.5(2) . .
C00C C008 C005 176.3(3) . .
C00E C009 C00I 120.0(2) . .
C00E C009 C00O 121.0(2) . .
C00I C009 C00O 119.0(2) . .
C00V C00A C002 177.2(3) . .
C00D C00B C00N 118.9(2) . .
C00D C00B C00V 119.9(2) . .
C00N C00B C00V 121.2(2) . .
C008 C00C C004 178.5(3) . .
C00R C00D C00B 120.8(2) . .
C00R C00D H00D 119.6 . .
C00B C00D H00D 119.6 . .
C00M C00E C009 119.9(2) . .
C00M C00E H00E 120.0 . .
C009 C00E H00E 120.0 . .
C00L C00F C004 120.5(2) . .
C00L C00F H00F 119.8 . .
C004 C00F H00F 119.8 . .
N001 C00G C007 178.6(3) . .
C00K C00H C007 119.7(2) . .
C00K C00H H00H 120.1 . .
C007 C00H H00H 120.1 . .
C00J C00I C009 120.2(2) . .
C00J C00I H00I 119.9 . .
C009 C00I H00I 119.9 . .
C00I C00J C002 120.4(2) . .
C00I C00J H00J 119.8 . .
C002 C00J H00J 119.8 . .
C00H C00K C004 120.6(2) . .
C00H C00K H00K 119.7 . .
C004 C00K H00K 119.7 . .
C00F C00L C007 119.8(2) . .
C00F C00L H00L 120.1 . .
C007 C00L H00L 120.1 . .
C00E C00M C002 121.0(2) . .
C00E C00M H00M 119.5 . .
C002 C00M H00M 119.5 . .
C00S C00N C00B 119.9(2) . .
C00S C00N H00N 120.1 . .
C00B C00N H00N 120.1 . .
N003 C00O C009 179.1(3) . .
C00R C00P C00S 119.8(2) . .
C00R C00P H00P 120.1 . .
C00S C00P H00P 120.1 . .
C00U C00Q C005 120.4(3) . .
C00U C00Q H00Q 119.8 . .
C005 C00Q H00Q 119.8 . .
C00D C00R C00P 120.0(2) . .
C00D C00R H00R 120.0 . .
C00P C00R H00R 120.0 . .
C00N C00S C00P 120.6(2) . .
C00N C00S H00S 119.7 . .
C00P C00S H00S 119.7 . .
C006 C00T C00W 120.4(3) . .
C006 C00T H00T 119.8 . .
C00W C00T H00T 119.8 . .
C00Q C00U C00W 120.4(2) . .
C00Q C00U H00U 119.8 . .
C00W C00U H00U 119.8 . .
C00A C00V C00B 176.6(3) . .
C00U C00W C00T 119.6(2) . .
C00U C00W H00W 120.2 . .
C00T C00W H00W 120.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N001 C00G 1.143(3) .
C002 C00M 1.396(3) .
C002 C00J 1.407(3) .
C002 C00A 1.421(3) .
N003 C00O 1.152(3) .
C004 C00K 1.395(3) .
C004 C00F 1.400(3) .
C004 C00C 1.428(3) .
C005 C00Q 1.391(3) .
C005 C006 1.393(3) .
C005 C008 1.424(3) .
C006 C00T 1.375(3) .
C006 H006 0.9500 .
C007 C00H 1.391(3) .
C007 C00L 1.392(3) .
C007 C00G 1.433(3) .
C008 C00C 1.200(3) .
C009 C00E 1.385(3) .
C009 C00I 1.390(3) .
C009 C00O 1.433(4) .
C00A C00V 1.204(3) .
C00B C00D 1.394(3) .
C00B C00N 1.397(3) .
C00B C00V 1.427(3) .
C00D C00R 1.372(3) .
C00D H00D 0.9500 .
C00E C00M 1.370(3) .
C00E H00E 0.9500 .
C00F C00L 1.370(3) .
C00F H00F 0.9500 .
C00H C00K 1.371(3) .
C00H H00H 0.9500 .
C00I C00J 1.368(3) .
C00I H00I 0.9500 .
C00J H00J 0.9500 .
C00K H00K 0.9500 .
C00L H00L 0.9500 .
C00M H00M 0.9500 .
C00N C00S 1.377(4) .
C00N H00N 0.9500 .
C00P C00R 1.382(4) .
C00P C00S 1.383(4) .
C00P H00P 0.9500 .
C00Q C00U 1.375(4) .
C00Q H00Q 0.9500 .
C00R H00R 0.9500 .
C00S H00S 0.9500 .
C00T C00W 1.385(4) .
C00T H00T 0.9500 .
C00U C00W 1.378(4) .
C00U H00U 0.9500 .
C00W H00W 0.9500 .
