#------------------------------------------------------------------------------
#$Date: 2012-10-17 11:23:33 +0300 (Wed, 17 Oct 2012) $
#$Revision: 68099 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/85/7108549.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_7108549
loop_
_publ_author_name
'Hubert Klein'
'Thierry Roisnel'
'Christian Bruneau'
'Sylvie Derien'
_publ_section_title
;
 One-step synthesis of 1-halo-1,3-butadienes via ruthenium-catalysed
 hydrohalogenative dimerisation of alkynes
;
_journal_name_full               Chem.Commun.
_journal_page_first              11032
_journal_volume                  48
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C16 H13 Cl'
_chemical_formula_sum            'C16 H13 Cl'
_chemical_formula_weight         240.71
_chemical_name_systematic
;
?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2012-01-09T09:12:45-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.6950(3)
_cell_length_b                   7.5345(5)
_cell_length_c                   28.7029(17)
_cell_measurement_reflns_used    7560
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.41
_cell_measurement_theta_min      2.8
_cell_measurement_wavelength     0.71073
_cell_volume                     1231.61(13)
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2006)'
_computing_data_collection       'Bruker APEX2 (Bruker, 2006)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2006)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material
;
WinGX publication routines (Farrugia, 1999),
CRYSCAL (T. Roisnel, local program)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.029
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            19579
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.44
_exptl_absorpt_coefficient_mu    0.283
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.04
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2831
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0326
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0396P)^2^+0.2037P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0738
_refine_ls_wR_factor_ref         0.077
_reflns_number_gt                2540
_reflns_number_total             2831
_reflns_threshold_expression     >2sigma(I)
_iucr_refine_instructions_details
;
.res file for SHELXL : job.res
.................................................................
TITL import in P 21 21 21
CELL 0.71073 5.6950 7.5345 28.7029 90.000 90.000 90.000
ZERR 4.00 0.0003 0.0005 0.0017 0.000 0.000 0.000
LATT -1
SYMM 1/2 - X, - Y, 1/2 + Z
SYMM 1/2 + X, 1/2 - Y, - Z
SYMM - X, 1/2 + Y, 1/2 - Z
SFAC C H CL
UNIT 64 52 4
MERG 2
FMAP 2
PLAN 20
ACTA
BOND $H
CONF
LIST 4
WPDB -2
L.S. 4
TEMP -123.00
WGHT 0.039600 0.203700
FVAR 0.79044
C1 1 0.876979 0.916247 0.003140 11.00000 0.02425 0.02641 =
0.02905 0.00148 0.00092 -0.00131
AFIX 43
H1 2 0.744636 0.861232 0.017189 11.00000 -1.20000
AFIX 0
C2 1 0.898137 0.917202 -0.044961 11.00000 0.03189 0.02961 =
0.02779 -0.00292 -0.00437 0.00007
AFIX 43
H2 2 0.780570 0.862894 -0.063618 11.00000 -1.20000
AFIX 0
C3 1 1.090533 0.997242 -0.065994 11.00000 0.03845 0.03112 =
0.02332 0.00001 0.00249 0.00375
AFIX 43
H3 2 1.104930 0.997638 -0.098968 11.00000 -1.20000
AFIX 0
C4 1 1.261038 1.076356 -0.038696 11.00000 0.03118 0.02956 =
0.03325 0.00178 0.00763 -0.00374
AFIX 43
H4 2 1.392537 1.131482 -0.053025 11.00000 -1.20000
AFIX 0
C5 1 1.241324 1.075753 0.009483 11.00000 0.02674 0.02743 =
0.03027 -0.00270 0.00097 -0.00390
AFIX 43
H5 2 1.359731 1.130312 0.027879 11.00000 -1.20000
AFIX 0
C6 1 1.048408 0.995431 0.031279 11.00000 0.02552 0.02076 =
0.02619 0.00008 0.00095 0.00146
C7 1 1.036684 0.996925 0.082295 11.00000 0.02670 0.02562 =
0.02672 -0.00234 -0.00179 -0.00089
AFIX 43
H7 2 1.170524 1.042860 0.097943 11.00000 -1.20000
AFIX 0
C8 1 0.860028 0.941349 0.109628 11.00000 0.02423 0.02523 =
0.02756 -0.00177 -0.00090 -0.00050
AFIX 43
H8 2 0.720519 0.897729 0.095551 11.00000 -1.20000
AFIX 0
C9 1 0.876198 0.946036 0.159908 11.00000 0.02179 0.02367 =
0.02907 -0.00166 -0.00057 -0.00040
AFIX 43
H9 2 1.014262 0.998702 0.172315 11.00000 -1.20000
AFIX 0
C10 1 0.720678 0.885336 0.191264 11.00000 0.01763 0.01962 =
0.02857 -0.00493 -0.00124 -0.00034
C11 1 0.751747 0.884066 0.242473 11.00000 0.02229 0.01572 =
0.02608 -0.00253 -0.00013 0.00334
C12 1 0.953541 0.960223 0.262421 11.00000 0.02312 0.02812 =
0.03041 -0.00004 0.00257 -0.00393
AFIX 43
H12 2 1.067023 1.015089 0.242900 11.00000 -1.20000
AFIX 0
C13 1 0.989068 0.956296 0.310198 11.00000 0.02667 0.02954 =
0.03026 -0.00190 -0.00606 -0.00075
AFIX 43
H13 2 1.126510 1.008148 0.323103 11.00000 -1.20000
AFIX 0
C14 1 0.825484 0.877285 0.339194 11.00000 0.03497 0.02629 =
0.02478 0.00101 -0.00026 0.00568
AFIX 43
H14 2 0.850388 0.875069 0.371916 11.00000 -1.20000
AFIX 0
C15 1 0.625220 0.801405 0.320342 11.00000 0.03014 0.02737 =
0.02966 0.00196 0.00475 0.00002
AFIX 43
H15 2 0.512780 0.746842 0.340156 11.00000 -1.20000
AFIX 0
C16 1 0.588665 0.805056 0.272416 11.00000 0.02109 0.02314 =
0.03307 -0.00221 0.00273 -0.00043
AFIX 43
H16 2 0.450611 0.753004 0.259828 11.00000 -1.20000
AFIX 0
CL1 3 0.459086 0.791043 0.171002 11.00000 0.02454 0.04864 =
0.02977 -0.00687 -0.00051 -0.01166
HKLF 4

REM import in P 21 21 21
REM R1 = 0.0326 for 2540 Fo > 4sig(Fo) and 0.0397 for all 2831 data
REM 154 parameters refined using 0 restraints

END

WGHT 0.0322 0.2229
REM Highest difference peak 0.24, deepest hole -0.20, 1-sigma level 0.04
Q1 1 0.9558 0.7198 0.3266 11.00000 0.05 0.24
Q2 1 1.0787 1.1629 0.1674 11.00000 0.05 0.23
Q3 1 0.6472 0.8953 0.2586 11.00000 0.05 0.16
Q4 1 0.7271 0.9000 0.2190 11.00000 0.05 0.16
Q5 1 1.0492 0.9991 0.0563 11.00000 0.05 0.16
Q6 1 1.3295 1.0454 0.0892 11.00000 0.05 0.16
Q7 1 0.7367 0.9783 0.1747 11.00000 0.05 0.16
Q8 1 1.2244 0.9870 -0.0543 11.00000 0.05 0.15
Q9 1 1.4092 1.0590 0.0312 11.00000 0.05 0.15
Q10 1 0.9262 0.9994 0.0172 11.00000 0.05 0.15
Q11 1 1.4425 0.9583 0.0104 11.00000 0.05 0.14
Q12 1 0.9366 1.0028 0.2905 11.00000 0.05 0.14
Q13 1 0.3535 0.6551 0.1576 11.00000 0.05 0.14
Q14 1 1.6073 1.1047 -0.0433 11.00000 0.05 0.14
Q15 1 0.1970 0.7040 0.2430 11.00000 0.05 0.13
Q16 1 1.1787 1.1493 0.3554 11.00000 0.05 0.13
Q17 1 1.0070 0.9147 0.0173 11.00000 0.05 0.13
Q18 1 1.3700 1.0219 0.2430 11.00000 0.05 0.13
Q19 1 1.2613 1.0256 -0.0152 11.00000 0.05 0.13
Q20 1 0.6970 0.7828 0.2582 11.00000 0.05 0.13
;
_[local]_cod_data_source_file    c2cc36422k.txt
_[local]_cod_data_source_block   HK1_Cl
_cod_database_code               7108549
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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
C1 C 0.8770(3) 0.9162(2) 0.00314(6) 0.0266(4) Uani 1 1 d .
H1 H 0.7446 0.8612 0.0172 0.032 Uiso 1 1 calc R
C2 C 0.8981(3) 0.9172(2) -0.04496(6) 0.0298(4) Uani 1 1 d .
H2 H 0.7806 0.8629 -0.0636 0.036 Uiso 1 1 calc R
C3 C 1.0905(3) 0.9972(2) -0.06599(6) 0.0310(4) Uani 1 1 d .
H3 H 1.1049 0.9976 -0.099 0.037 Uiso 1 1 calc R
C4 C 1.2610(3) 1.0764(2) -0.03870(6) 0.0313(4) Uani 1 1 d .
H4 H 1.3925 1.1315 -0.053 0.038 Uiso 1 1 calc R
C5 C 1.2413(3) 1.0758(2) 0.00948(6) 0.0281(4) Uani 1 1 d .
H5 H 1.3597 1.1303 0.0279 0.034 Uiso 1 1 calc R
C6 C 1.0484(3) 0.9954(2) 0.03128(5) 0.0242(3) Uani 1 1 d .
C7 C 1.0367(3) 0.9969(2) 0.08229(6) 0.0263(3) Uani 1 1 d .
H7 H 1.1705 1.0429 0.0979 0.032 Uiso 1 1 calc R
C8 C 0.8600(3) 0.9413(2) 0.10963(6) 0.0257(3) Uani 1 1 d .
H8 H 0.7205 0.8977 0.0956 0.031 Uiso 1 1 calc R
C9 C 0.8762(3) 0.9460(2) 0.15991(6) 0.0248(3) Uani 1 1 d .
H9 H 1.0143 0.9987 0.1723 0.03 Uiso 1 1 calc R
C10 C 0.7207(3) 0.8853(2) 0.19126(5) 0.0219(3) Uani 1 1 d .
C11 C 0.7517(3) 0.8841(2) 0.24247(5) 0.0214(3) Uani 1 1 d .
C12 C 0.9535(3) 0.9602(2) 0.26242(6) 0.0272(3) Uani 1 1 d .
H12 H 1.067 1.0151 0.2429 0.033 Uiso 1 1 calc R
C13 C 0.9891(3) 0.9563(2) 0.31020(6) 0.0288(4) Uani 1 1 d .
H13 H 1.1265 1.0081 0.3231 0.035 Uiso 1 1 calc R
C14 C 0.8255(3) 0.8773(2) 0.33919(6) 0.0287(4) Uani 1 1 d .
H14 H 0.8504 0.8751 0.3719 0.034 Uiso 1 1 calc R
C15 C 0.6252(3) 0.8014(2) 0.32034(5) 0.0291(4) Uani 1 1 d .
H15 H 0.5128 0.7468 0.3402 0.035 Uiso 1 1 calc R
C16 C 0.5887(3) 0.8051(2) 0.27242(6) 0.0258(3) Uani 1 1 d .
H16 H 0.4506 0.753 0.2598 0.031 Uiso 1 1 calc R
Cl1 Cl 0.45909(7) 0.79104(6) 0.171002(14) 0.03431(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
C1 0.0243(7) 0.0264(9) 0.0291(9) 0.0015(7) 0.0009(7) -0.0013(7)
C2 0.0319(9) 0.0296(9) 0.0278(9) -0.0029(7) -0.0044(7) 0.0001(7)
C3 0.0384(10) 0.0311(9) 0.0233(8) 0.0000(7) 0.0025(7) 0.0038(8)
C4 0.0312(9) 0.0296(9) 0.0332(9) 0.0018(8) 0.0076(7) -0.0037(7)
C5 0.0267(8) 0.0274(9) 0.0303(9) -0.0027(7) 0.0010(7) -0.0039(7)
C6 0.0255(7) 0.0208(8) 0.0262(8) 0.0001(6) 0.0010(7) 0.0015(7)
C7 0.0267(7) 0.0256(8) 0.0267(8) -0.0023(7) -0.0018(7) -0.0009(7)
C8 0.0242(7) 0.0252(9) 0.0276(8) -0.0018(7) -0.0009(7) -0.0005(7)
C9 0.0218(7) 0.0237(8) 0.0291(9) -0.0017(7) -0.0006(6) -0.0004(6)
C10 0.0176(7) 0.0196(8) 0.0286(8) -0.0049(6) -0.0012(6) -0.0003(6)
C11 0.0223(7) 0.0157(8) 0.0261(8) -0.0025(6) -0.0001(6) 0.0033(6)
C12 0.0231(7) 0.0281(9) 0.0304(9) 0.0000(7) 0.0026(7) -0.0039(7)
C13 0.0267(9) 0.0295(9) 0.0303(8) -0.0019(7) -0.0061(7) -0.0007(7)
C14 0.0350(9) 0.0263(9) 0.0248(9) 0.0010(7) -0.0003(7) 0.0057(7)
C15 0.0301(7) 0.0274(8) 0.0297(9) 0.0020(8) 0.0048(7) 0.0000(7)
C16 0.0211(7) 0.0231(8) 0.0331(8) -0.0022(7) 0.0027(6) -0.0004(6)
Cl1 0.02454(17) 0.0486(3) 0.0298(2) -0.0069(2) -0.00051(16) -0.01166(18)
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 0 '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
C2 C1 C6 120.78(16)
C2 C1 H1 119.6
C6 C1 H1 119.6
C1 C2 C3 120.26(16)
C1 C2 H2 119.9
C3 C2 H2 119.9
C4 C3 C2 119.66(15)
C4 C3 H3 120.2
C2 C3 H3 120.2
C3 C4 C5 120.43(16)
C3 C4 H4 119.8
C5 C4 H4 119.8
C4 C5 C6 120.64(16)
C4 C5 H5 119.7
C6 C5 H5 119.7
C1 C6 C5 118.22(15)
C1 C6 C7 123.20(15)
C5 C6 C7 118.57(15)
C8 C7 C6 127.98(16)
C8 C7 H7 116
C6 C7 H7 116
C7 C8 C9 121.84(16)
C7 C8 H8 119.1
C9 C8 H8 119.1
C10 C9 C8 128.19(15)
C10 C9 H9 115.9
C8 C9 H9 115.9
C9 C10 C11 126.07(14)
C9 C10 Cl1 118.49(12)
C11 C10 Cl1 115.41(11)
C16 C11 C12 117.79(14)
C16 C11 C10 122.24(14)
C12 C11 C10 119.95(14)
C13 C12 C11 120.88(15)
C13 C12 H12 119.6
C11 C12 H12 119.6
C14 C13 C12 120.38(16)
C14 C13 H13 119.8
C12 C13 H13 119.8
C13 C14 C15 119.78(15)
C13 C14 H14 120.1
C15 C14 H14 120.1
C14 C15 C16 120.06(15)
C14 C15 H15 120
C16 C15 H15 120
C15 C16 C11 121.10(15)
C15 C16 H16 119.4
C11 C16 H16 119.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.386(2)
C1 C6 1.401(2)
C1 H1 0.95
C2 C3 1.389(2)
C2 H2 0.95
C3 C4 1.383(2)
C3 H3 0.95
C4 C5 1.387(2)
C4 H4 0.95
C5 C6 1.402(2)
C5 H5 0.95
C6 C7 1.466(2)
C7 C8 1.343(2)
C7 H7 0.95
C8 C9 1.447(2)
C8 H8 0.95
C9 C10 1.343(2)
C9 H9 0.95
C10 C11 1.480(2)
C10 Cl1 1.7500(15)
C11 C16 1.398(2)
C11 C12 1.406(2)
C12 C13 1.387(2)
C12 H12 0.95
C13 C14 1.384(2)
C13 H13 0.95
C14 C15 1.386(2)
C14 H14 0.95
C15 C16 1.392(2)
C15 H15 0.95
C16 H16 0.95
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
C6 C1 C2 C3 -0.1(3)
C1 C2 C3 C4 -0.1(3)
C2 C3 C4 C5 0.2(3)
C3 C4 C5 C6 -0.1(3)
C2 C1 C6 C5 0.1(2)
C2 C1 C6 C7 -179.35(16)
C4 C5 C6 C1 0.0(2)
C4 C5 C6 C7 179.46(15)
C1 C6 C7 C8 -6.6(3)
C5 C6 C7 C8 173.96(16)
C6 C7 C8 C9 178.08(15)
C7 C8 C9 C10 -175.57(17)
C8 C9 C10 C11 176.25(15)
C8 C9 C10 Cl1 -1.4(2)
C9 C10 C11 C16 -174.67(15)
Cl1 C10 C11 C16 3.0(2)
C9 C10 C11 C12 3.7(2)
Cl1 C10 C11 C12 -178.57(11)
C16 C11 C12 C13 0.2(2)
C10 C11 C12 C13 -178.28(15)
C11 C12 C13 C14 -0.1(2)
C12 C13 C14 C15 0.1(2)
C13 C14 C15 C16 -0.1(2)
C14 C15 C16 C11 0.2(2)
C12 C11 C16 C15 -0.2(2)
C10 C11 C16 C15 178.21(15)