#------------------------------------------------------------------------------
#$Date: 2016-03-26 21:03:43 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180463 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/32/7213291.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7213291
loop_
_publ_author_name
'Kovtonyuk, Vladimir N.'
'Kobrina, Ljubov S.'
'Gatilov, Yurij V.'
'Bagryanskaya, Irina Yu.'
'Fröhlich, Roland'
'Haufe, Günter'
_publ_section_title
;
 Reactions of polyfluorinated cyclohexadienones with diazoalkanes. Part 1.
 Formation of cyclopropanes from polyfluorinated cyclohexa-2,4-dienones
 with diazomethane and phenyldiazomethane
;
_journal_issue                   12
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              1929
_journal_paper_doi               10.1039/b001618g
_journal_year                    2000
_chemical_formula_sum            'C13 H6 Cl F5 O'
_chemical_formula_weight         308.63
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 91.28(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.205(1)
_cell_length_b                   13.755(1)
_cell_length_c                   7.725(1)
_cell_measurement_temperature    198(2)
_cell_volume                     1190.3(2)
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP (Siemens Analytical)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      198(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode Nonius FR591'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            9988
_diffrn_reflns_theta_full        30.48
_diffrn_reflns_theta_max         30.48
_diffrn_reflns_theta_min         2.96
_exptl_absorpt_coefficient_mu    0.377
_exptl_absorpt_correction_T_max  0.9284
_exptl_absorpt_correction_T_min  0.8639
_exptl_absorpt_correction_type   'SORTAV (Blessing, 1995 & 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.722
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    'refined as riding atoms'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3517
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0411
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0341P)²+0.5607P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.1047
_reflns_number_gt                2683
_reflns_number_total             3517
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b001618gsup1.cif
_cod_data_source_block           haf_960
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7213291
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C2 C 0.60304(13) 0.87993(11) 0.3538(2) 0.0304(3) Uani 1 1 d .
O2 O 0.50230(10) 0.85245(10) 0.36312(18) 0.0453(3) Uani 1 1 d .
C3 C 0.68395(15) 0.83537(12) 0.2159(2) 0.0333(3) Uani 1 1 d .
F3 F 0.64528(10) 0.74237(8) 0.18639(14) 0.0456(3) Uani 1 1 d .
Cl3 Cl 0.66234(5) 0.89917(4) 0.01828(5) 0.05004(15) Uani 1 1 d .
C4 C 0.81213(14) 0.83330(12) 0.2665(2) 0.0342(3) Uani 1 1 d .
F4 F 0.88122(10) 0.78339(9) 0.15869(15) 0.0526(3) Uani 1 1 d .
C5 C 0.85920(13) 0.88194(12) 0.3970(2) 0.0319(3) Uani 1 1 d .
F5 F 0.97740(8) 0.88209(9) 0.42558(15) 0.0473(3) Uani 1 1 d .
C6 C 0.79116(13) 0.94584(12) 0.51129(18) 0.0290(3) Uani 1 1 d .
F6 F 0.83102(9) 0.94228(8) 0.67927(12) 0.0412(2) Uani 1 1 d .
C1 C 0.65802(13) 0.94854(12) 0.48079(18) 0.0284(3) Uani 1 1 d .
F1 F 0.59223(8) 0.95433(7) 0.62601(12) 0.0370(2) Uani 1 1 d .
C7 C 0.73469(13) 1.03821(11) 0.44784(19) 0.0293(3) Uani 1 1 d .
H7 H 0.7281 1.0881 0.5413 0.035 Uiso 1 1 calc R
C8 C 0.75619(13) 1.08241(11) 0.27472(19) 0.0287(3) Uani 1 1 d .
C13 C 0.66389(14) 1.12926(12) 0.1862(2) 0.0346(3) Uani 1 1 d .
H13 H 0.5867 1.1318 0.2345 0.042 Uiso 1 1 calc R
C12 C 0.68376(17) 1.17242(14) 0.0275(2) 0.0430(4) Uani 1 1 d .
H12 H 0.6203 1.2047 -0.0325 0.052 Uiso 1 1 calc R
C11 C 0.79520(19) 1.16866(15) -0.0436(3) 0.0487(5) Uani 1 1 d .
H11 H 0.8082 1.1971 -0.1536 0.058 Uiso 1 1 calc R
C10 C 0.88796(17) 1.12350(15) 0.0450(3) 0.0504(5) Uani 1 1 d .
H10 H 0.9652 1.1219 -0.0032 0.061 Uiso 1 1 calc R
C9 C 0.86891(15) 1.08053(13) 0.2038(2) 0.0385(4) Uani 1 1 d .
H9 H 0.9331 1.0497 0.2645 0.046 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O2 C2 C1 122.67(15)
O2 C2 C3 119.17(15)
C1 C2 C3 117.88(13)
F3 C3 C4 109.14(14)
F3 C3 C2 107.34(12)
C4 C3 C2 114.05(13)
F3 C3 Cl3 106.43(10)
C4 C3 Cl3 110.48(11)
C2 C3 Cl3 109.09(11)
C5 C4 F4 120.77(15)
C5 C4 C3 124.37(14)
F4 C4 C3 114.64(14)
C4 C5 F5 120.50(14)
C4 C5 C6 124.17(14)
F5 C5 C6 115.11(14)
F6 C6 C5 112.75(13)
F6 C6 C7 117.98(13)
C5 C6 C7 122.11(13)
F6 C6 C1 116.88(12)
C5 C6 C1 116.47(13)
C7 C6 C1 61.16(10)
F1 C1 C2 110.98(12)
F1 C1 C6 115.23(12)
C2 C1 C6 118.86(13)
F1 C1 C7 114.07(13)
C2 C1 C7 129.01(12)
C6 C1 C7 59.14(10)
C8 C7 C6 124.28(13)
C8 C7 C1 125.48(13)
C6 C7 C1 59.70(10)
C13 C8 C9 119.29(15)
C13 C8 C7 119.85(13)
C9 C8 C7 120.81(15)
C12 C13 C8 120.22(15)
C11 C12 C13 120.16(17)
C12 C11 C10 119.95(17)
C11 C10 C9 120.21(17)
C10 C9 C8 120.14(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C2 O2 1.1941(19)
C2 C1 1.485(2)
C2 C3 1.541(2)
C3 F3 1.3680(18)
C3 C4 1.480(2)
C3 Cl3 1.7727(16)
C4 C5 1.311(2)
C4 F4 1.3388(18)
C5 F5 1.3378(18)
C5 C6 1.471(2)
C6 F6 1.3637(17)
C6 C7 1.497(2)
C6 C1 1.506(2)
C1 F1 1.3584(15)
C1 C7 1.528(2)
C7 C8 1.494(2)
C8 C13 1.386(2)
C8 C9 1.388(2)
C13 C12 1.384(2)
C12 C11 1.376(3)
C11 C10 1.379(3)
C10 C9 1.382(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
O2 C2 C3 F3 -29.2(2)
C1 C2 C3 F3 144.86(13)
O2 C2 C3 C4 -150.24(15)
C1 C2 C3 C4 23.8(2)
O2 C2 C3 Cl3 85.71(16)
C1 C2 C3 Cl3 -100.22(14)
F3 C3 C4 C5 -133.90(16)
C2 C3 C4 C5 -13.9(2)
Cl3 C3 C4 C5 109.41(17)
F3 C3 C4 F4 51.52(18)
C2 C3 C4 F4 171.54(13)
Cl3 C3 C4 F4 -65.16(16)
F4 C4 C5 F5 -0.4(2)
C3 C4 C5 F5 -174.68(14)
F4 C4 C5 C6 174.00(15)
C3 C4 C5 C6 -0.3(3)
C4 C5 C6 F6 143.57(16)
F5 C5 C6 F6 -41.75(19)
C4 C5 C6 C7 -66.7(2)
F5 C5 C6 C7 107.99(16)
C4 C5 C6 C1 4.4(2)
F5 C5 C6 C1 179.10(13)
O2 C2 C1 F1 15.9(2)
C3 C2 C1 F1 -157.96(13)
O2 C2 C1 C6 152.99(15)
C3 C2 C1 C6 -20.9(2)
O2 C2 C1 C7 -134.90(17)
C3 C2 C1 C7 51.2(2)
F6 C6 C1 F1 4.6(2)
C5 C6 C1 F1 142.08(14)
C7 C6 C1 F1 -104.11(14)
F6 C6 C1 C2 -130.74(14)
C5 C6 C1 C2 6.7(2)
C7 C6 C1 C2 120.52(15)
F6 C6 C1 C7 108.74(15)
C5 C6 C1 C7 -113.81(15)
F6 C6 C7 C8 138.49(15)
C5 C6 C7 C8 -9.8(2)
C1 C6 C7 C8 -114.54(16)
F6 C6 C7 C1 -106.97(14)
C5 C6 C7 C1 104.79(16)
F1 C1 C7 C8 -141.31(15)
C2 C1 C7 C8 8.8(2)
C6 C1 C7 C8 112.61(17)
F1 C1 C7 C6 106.08(14)
C2 C1 C7 C6 -103.86(17)
C6 C7 C8 C13 144.18(16)
C1 C7 C8 C13 69.5(2)
C6 C7 C8 C9 -38.3(2)
C1 C7 C8 C9 -113.01(18)
C9 C8 C13 C12 0.9(3)
C7 C8 C13 C12 178.48(16)
C8 C13 C12 C11 0.3(3)
C13 C12 C11 C10 -1.3(3)
C12 C11 C10 C9 1.1(3)
C11 C10 C9 C8 0.2(3)
C13 C8 C9 C10 -1.2(3)
C7 C8 C9 C10 -178.68(17)
