#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/64/4106400.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_4106400
loop_
_publ_author_name
'Zhong-Ke Yao'
'Zhi-Xiang Yu'
_publ_section_title
;
 Mechanisms of the Thermal Cyclotrimerizations of Fluoro- and
 Chloroacetylenes: Density Functional Theory Investigation and
 Intermediate Trapping Experiments
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10864
_journal_page_last               10877
_journal_paper_doi               10.1021/ja2021476
_journal_volume                  133
_journal_year                    2011
_chemical_formula_sum            'C12 H7.5 Cl1.5'
_chemical_formula_weight         204.85
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 130.56(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.834(3)
_cell_length_b                   17.699(4)
_cell_length_c                   10.490(2)
_cell_measurement_reflns_used    4410
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.44
_cell_volume                     1951.3(11)
_computing_cell_refinement       'Rapid Auto(Rigaku 2001)'
_computing_data_collection       'Rapid Auto(Rigaku 2001)'
_computing_data_reduction        'Rapid Auto(Rigaku 2001)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material  'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku raxis Rapid IP Area Detector'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_av_sigmaI/netI    0.0319
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4410
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.44
_exptl_absorpt_coefficient_mu    0.475
_exptl_absorpt_correction_T_max  0.8039
_exptl_absorpt_correction_T_min  0.7700
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR by T.Higashi    8 March, 1995'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.53
_exptl_crystal_size_min          0.48
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     125
_refine_ls_number_reflns         2242
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0333
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0455P)²+0.1845P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0801
_refine_ls_wR_factor_ref         0.0844
_reflns_number_gt                1991
_reflns_number_total             2242
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja2021476_si_003.cif
_cod_data_source_block           sx2684
_cod_original_cell_volume        1951.6(11)
_cod_original_formula_sum        'C12 H7.50 Cl1.50'
_cod_database_code               4106400
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
Cl1 Cl 0.35400(4) 0.09563(2) 0.83574(5) 0.02885(12) Uani 1 1 d .
Cl2 Cl 0.5000 0.00882(3) 0.7500 0.03580(16) Uani 1 2 d S
C1 C 0.43517(12) 0.14582(8) 0.78868(16) 0.0219(3) Uani 1 1 d .
C2 C 0.43334(12) 0.22471(8) 0.78875(16) 0.0207(3) Uani 1 1 d .
C3 C 0.36252(13) 0.26841(8) 0.82697(17) 0.0219(3) Uani 1 1 d .
C4 C 0.5000 0.34804(11) 0.7500 0.0235(4) Uani 1 2 d S
C5 C 0.5000 0.26364(11) 0.7500 0.0205(4) Uani 1 2 d S
C6 C 0.5000 0.10616(11) 0.7500 0.0228(4) Uani 1 2 d S
C7 C 0.26015(13) 0.31412(8) 0.70386(18) 0.0264(3) Uani 1 1 d .
H7A H 0.2304 0.3134 0.5929 0.032 Uiso 1 1 calc R
C8 C 0.34341(15) 0.31496(9) 1.02564(19) 0.0303(3) Uani 1 1 d .
H8A H 0.3712 0.3149 1.1356 0.036 Uiso 1 1 calc R
C9 C 0.24363(15) 0.36104(9) 0.9035(2) 0.0313(3) Uani 1 1 d .
H9A H 0.2040 0.3931 0.9303 0.038 Uiso 1 1 calc R
C10 C 0.43681(15) 0.38768(9) 0.6007(2) 0.0301(3) Uani 1 1 d .
H10A H 0.3938 0.3610 0.4981 0.036 Uiso 1 1 calc R
C11 C 0.40309(14) 0.26890(8) 0.98830(18) 0.0258(3) Uani 1 1 d .
H11A H 0.4719 0.2376 1.0729 0.031 Uiso 1 1 calc R
C12 C 0.20147(14) 0.36059(9) 0.7425(2) 0.0308(3) Uani 1 1 d .
H12A H 0.1325 0.3920 0.6585 0.037 Uiso 1 1 calc R
C13 C 0.43618(18) 0.46592(10) 0.6007(2) 0.0446(4) Uani 1 1 d .
H13A H 0.3919 0.4928 0.4982 0.053 Uiso 1 1 calc R
C14 C 0.5000 0.50469(14) 0.7500 0.0531(8) Uani 1 2 d S
H14A H 0.5000 0.5584 0.7500 0.064 Uiso 1 2 calc SR
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'
Cl Cl 0.1484 0.1585 '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
C6 C1 C2 121.34(13) . .
C6 C1 Cl1 118.92(11) . .
C2 C1 Cl1 119.74(11) . .
C1 C2 C5 118.30(13) . .
C1 C2 C3 122.23(12) . .
C5 C2 C3 119.47(13) . .
C11 C3 C7 119.00(13) . .
C11 C3 C2 120.83(13) . .
C7 C3 C2 119.99(12) . .
C10 C4 C10 119.3(2) 2_656 .
C10 C4 C5 120.35(10) 2_656 .
C10 C4 C5 120.35(10) . .
C2 C5 C2 121.34(17) 2_656 .
C2 C5 C4 119.33(9) 2_656 .
C2 C5 C4 119.33(9) . .
C1 C6 C1 119.38(18) 2_656 .
C1 C6 Cl2 120.31(9) 2_656 .
C1 C6 Cl2 120.31(9) . .
C12 C7 C3 120.47(14) . .
C12 C7 H7A 119.8 . .
C3 C7 H7A 119.8 . .
C9 C8 C11 120.30(14) . .
C9 C8 H8A 119.8 . .
C11 C8 H8A 119.8 . .
C8 C9 C12 120.15(14) . .
C8 C9 H9A 119.9 . .
C12 C9 H9A 119.9 . .
C13 C10 C4 120.30(16) . .
C13 C10 H10A 119.8 . .
C4 C10 H10A 119.8 . .
C8 C11 C3 120.21(14) . .
C8 C11 H11A 119.9 . .
C3 C11 H11A 119.9 . .
C9 C12 C7 119.86(14) . .
C9 C12 H12A 120.1 . .
C7 C12 H12A 120.1 . .
C14 C13 C10 119.86(17) . .
C14 C13 H13A 120.1 . .
C10 C13 H13A 120.1 . .
C13 C14 C13 120.4(2) . 2_656
C13 C14 H14A 119.8 . .
C13 C14 H14A 119.8 2_656 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C1 1.7364(14) .
Cl2 C6 1.723(2) .
C1 C6 1.3910(17) .
C1 C2 1.3966(19) .
C2 C5 1.4064(16) .
C2 C3 1.4932(19) .
C3 C11 1.394(2) .
C3 C7 1.396(2) .
C4 C10 1.3888(19) 2_656
C4 C10 1.3888(19) .
C4 C5 1.494(3) .
C5 C2 1.4064(16) 2_656
C6 C1 1.3910(17) 2_656
C7 C12 1.388(2) .
C7 H7A 0.9500 .
C8 C9 1.383(2) .
C8 C11 1.386(2) .
C8 H8A 0.9500 .
C9 C12 1.383(2) .
C9 H9A 0.9500 .
C10 C13 1.385(2) .
C10 H10A 0.9500 .
C11 H11A 0.9500 .
C12 H12A 0.9500 .
C13 C14 1.380(2) .
C13 H13A 0.9500 .
C14 C13 1.380(2) 2_656
C14 H14A 0.9500 .
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_4
C6 C1 C2 C5 -0.57(18) . .
Cl1 C1 C2 C5 -179.96(8) . .
C6 C1 C2 C3 178.92(10) . .
Cl1 C1 C2 C3 -0.48(18) . .
C1 C2 C3 C11 69.05(19) . .
C5 C2 C3 C11 -111.47(14) . .
C1 C2 C3 C7 -115.91(15) . .
C5 C2 C3 C7 63.57(17) . .
C1 C2 C5 C2 0.28(9) . 2_656
C3 C2 C5 C2 -179.22(13) . 2_656
C1 C2 C5 C4 -179.72(9) . .
C3 C2 C5 C4 0.78(13) . .
C10 C4 C5 C2 -111.49(10) 2_656 2_656
C10 C4 C5 C2 68.51(10) . 2_656
C10 C4 C5 C2 68.51(10) 2_656 .
C10 C4 C5 C2 -111.49(10) . .
C2 C1 C6 C1 0.29(9) . 2_656
Cl1 C1 C6 C1 179.69(11) . 2_656
C2 C1 C6 Cl2 -179.71(9) . .
Cl1 C1 C6 Cl2 -0.31(11) . .
C11 C3 C7 C12 1.4(2) . .
C2 C3 C7 C12 -173.73(13) . .
C11 C8 C9 C12 1.0(2) . .
C10 C4 C10 C13 -0.42(12) 2_656 .
C5 C4 C10 C13 179.58(12) . .
C9 C8 C11 C3 -0.3(2) . .
C7 C3 C11 C8 -0.9(2) . .
C2 C3 C11 C8 174.22(13) . .
C8 C9 C12 C7 -0.5(2) . .
C3 C7 C12 C9 -0.7(2) . .
C4 C10 C13 C14 0.8(2) . .
C10 C13 C14 C13 -0.41(12) . 2_656
