#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:36:43 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180189 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/85/7108550.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_7108550
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_paper_doi               10.1039/c2cc36422k
_journal_volume                  48
_journal_year                    2012
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C18 H11 Cl N2'
_chemical_formula_sum            'C18 H11 Cl N2'
_chemical_formula_weight         290.74
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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_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             2012-04-20T17:30:39-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 108.455(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0766(6)
_cell_length_b                   10.0123(6)
_cell_length_c                   13.7838(7)
_cell_measurement_reflns_used    2022
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.47
_cell_measurement_theta_min      2.56
_cell_measurement_wavelength     0.71073
_cell_volume                     1450.04(14)
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0487
_diffrn_reflns_av_unetI/netI     0.0619
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10141
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.11
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.808
_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    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3304
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0473
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0492P)^2^+0.0188P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1144
_reflns_number_gt                2346
_reflns_number_total             3304
_reflns_threshold_expression     >2sigma(I)
_iucr_refine_instructions_details
;
.res file for SHELXL : job.res
.................................................................
TITL import in P 21/c
CELL 0.71073 11.0766 10.0123 13.7838 90.000 108.455 90.000
ZERR 4.00 0.0006 0.0006 0.0007 0.000 0.002 0.000
LATT 1
SYMM - X, 1/2 + Y, 1/2 - Z
SFAC C H N CL
UNIT 72 44 8 4
MERG 2
FMAP 2
PLAN 20
ACTA
BOND $H
CONF
LIST 4
WPDB -2
L.S. 4
TEMP -123.00
WGHT 0.049200 0.018800
FVAR 0.92375
CL1 4 0.668359 -0.045573 0.276996 11.00000 0.05413 0.02376 =
0.04040 0.00572 0.00153 0.00364
N1 3 0.371455 0.387208 -0.201459 11.00000 0.05520 0.04157 =
0.02834 0.00084 0.00287 0.00531
C2 1 0.426527 0.344673 -0.123296 11.00000 0.03931 0.02821 =
0.02540 -0.00362 0.00751 0.00252
C3 1 0.492991 0.291116 -0.023105 11.00000 0.02961 0.02768 =
0.02272 -0.00278 0.00701 0.00587
C4 1 0.605296 0.349109 0.038276 11.00000 0.03826 0.02534 =
0.02436 -0.00146 0.01134 -0.00139
AFIX 43
H4 2 0.639321 0.425153 0.014894 11.00000 -1.20000
AFIX 0
C5 1 0.667283 0.295377 0.133710 11.00000 0.02868 0.02681 =
0.02534 -0.00366 0.00628 -0.00086
AFIX 43
H5 2 0.745118 0.333556 0.174980 11.00000 -1.20000
AFIX 0
C6 1 0.616643 0.186105 0.169644 11.00000 0.02711 0.02494 =
0.02496 -0.00226 0.00740 0.00576
C7 1 0.503934 0.128574 0.106786 11.00000 0.03170 0.02742 =
0.03076 0.00206 0.00843 -0.00198
AFIX 43
H7 2 0.469188 0.053030 0.130158 11.00000 -1.20000
AFIX 0
C8 1 0.442737 0.180660 0.011036 11.00000 0.02680 0.03341 =
0.02826 -0.00295 0.00472 -0.00095
AFIX 43
H8 2 0.366371 0.140866 -0.031326 11.00000 -1.20000
AFIX 0
C9 1 0.682675 0.128397 0.271404 11.00000 0.03078 0.02331 =
0.02902 0.00402 0.00641 0.00412
N11 3 0.940134 1.027263 0.626455 11.00000 0.04897 0.03794 =
0.04068 -0.00252 0.00712 0.00043
C12 1 0.923560 0.916786 0.604694 11.00000 0.03009 0.03857 =
0.02857 0.00084 0.00234 0.00364
C13 1 0.900831 0.779330 0.573309 11.00000 0.02370 0.03228 =
0.02989 0.00046 0.00297 0.00202
C14 1 0.867751 0.748582 0.469139 11.00000 0.02977 0.03335 =
0.02513 0.00572 0.00138 0.00339
AFIX 43
H14 2 0.861909 0.817610 0.420576 11.00000 -1.20000
AFIX 0
C15 1 0.843752 0.618659 0.437168 11.00000 0.02688 0.03553 =
0.02004 0.00136 0.00060 0.00171
AFIX 43
H15 2 0.821032 0.599016 0.366222 11.00000 -1.20000
AFIX 0
C16 1 0.851935 0.514582 0.506467 11.00000 0.02063 0.03329 =
0.02332 -0.00114 0.00207 0.00251
C17 1 0.888453 0.547135 0.611185 11.00000 0.02805 0.03546 =
0.02315 0.00595 0.00368 0.00256
AFIX 43
H17 2 0.897260 0.477841 0.660026 11.00000 -1.20000
AFIX 0
C18 1 0.911717 0.677440 0.644393 11.00000 0.03014 0.03782 =
0.02187 -0.00034 0.00302 0.00132
AFIX 43
H18 2 0.935014 0.697554 0.715291 11.00000 -1.20000
AFIX 0
C19 1 0.827224 0.375699 0.474657 11.00000 0.02487 0.03002 =
0.02608 0.00541 0.00431 0.00150
AFIX 43
H19 2 0.858175 0.309612 0.525995 11.00000 -1.20000
AFIX 0
C20 1 0.764835 0.331963 0.379648 11.00000 0.02559 0.03051 =
0.02601 0.00251 0.00627 0.00303
AFIX 43
H20 2 0.731246 0.394437 0.325989 11.00000 -1.20000
AFIX 0
C21 1 0.748658 0.190479 0.358804 11.00000 0.02852 0.02981 =
0.02756 0.00710 0.00586 0.00535
AFIX 43
H21 2 0.790289 0.133411 0.414391 11.00000 -1.20000
HKLF 4

REM import in P 21/c
REM R1 = 0.0473 for 2346 Fo > 4sig(Fo) and 0.0756 for all 3304 data
REM 190 parameters refined using 0 restraints

END

WGHT 0.0440 0.1023
REM Highest difference peak 0.23, deepest hole -0.31, 1-sigma level 0.05
Q1 1 0.9233 0.7206 0.6028 11.00000 0.05 0.23
Q2 1 0.8989 0.5296 0.5580 11.00000 0.05 0.22
Q3 1 0.6619 0.1633 0.2152 11.00000 0.05 0.22
Q4 1 0.8174 0.4561 0.4810 11.00000 0.05 0.20
Q5 1 0.5564 0.1764 0.1501 11.00000 0.05 0.20
Q6 1 0.7795 0.2644 0.3488 11.00000 0.05 0.20
Q7 1 0.4773 0.2232 -0.0219 11.00000 0.05 0.20
Q8 1 0.9247 0.9862 0.5716 11.00000 0.05 0.19
Q9 1 0.6183 0.3338 0.0876 11.00000 0.05 0.19
Q10 1 0.9070 0.9633 0.6437 11.00000 0.05 0.19
Q11 1 0.6647 0.0583 0.2792 11.00000 0.05 0.19
Q12 1 0.5435 0.3211 0.0016 11.00000 0.05 0.19
Q13 1 0.5953 -0.0640 0.2088 11.00000 0.05 0.18
Q14 1 0.9491 0.6882 0.6890 11.00000 0.05 0.18
Q15 1 0.8558 0.7621 0.5322 11.00000 0.05 0.17
Q16 1 1.0013 0.9562 0.6053 11.00000 0.05 0.17
Q17 1 0.9110 0.7506 0.5285 11.00000 0.05 0.17
Q18 1 0.7556 0.1611 0.3140 11.00000 0.05 0.17
Q19 1 0.7948 0.3536 0.4224 11.00000 0.05 0.17
Q20 1 0.9242 0.8326 0.5777 11.00000 0.05 0.17
;
_cod_data_source_file            c2cc36422k.txt
_cod_data_source_block           HKPCN1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7108550
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
Cl1 Cl 0.66836(5) -0.04557(5) 0.27700(3) 0.04258(18) Uani 1 1 d .
N1 N 0.37145(16) 0.38721(18) -0.20146(11) 0.0441(5) Uani 1 1 d .
C2 C 0.42653(18) 0.34467(19) -0.12330(13) 0.0316(4) Uani 1 1 d .
C3 C 0.49299(17) 0.29112(18) -0.02310(12) 0.0270(4) Uani 1 1 d .
C4 C 0.60530(17) 0.34911(19) 0.03828(12) 0.0290(4) Uani 1 1 d .
H4 H 0.6393 0.4252 0.0149 0.035 Uiso 1 1 calc R
C5 C 0.66728(17) 0.29538(18) 0.13371(12) 0.0275(4) Uani 1 1 d .
H5 H 0.7451 0.3336 0.175 0.033 Uiso 1 1 calc R
C6 C 0.61664(16) 0.18611(18) 0.16964(12) 0.0259(4) Uani 1 1 d .
C7 C 0.50393(17) 0.12857(19) 0.10679(12) 0.0303(4) Uani 1 1 d .
H7 H 0.4692 0.053 0.1302 0.036 Uiso 1 1 calc R
C8 C 0.44274(17) 0.18066(19) 0.01104(12) 0.0304(4) Uani 1 1 d .
H8 H 0.3664 0.1409 -0.0313 0.037 Uiso 1 1 calc R
C9 C 0.68268(17) 0.12840(19) 0.27140(12) 0.0284(4) Uani 1 1 d .
N11 N 0.94013(17) 1.02726(18) 0.62646(12) 0.0442(4) Uani 1 1 d .
C12 C 0.92356(18) 0.9168(2) 0.60469(13) 0.0340(5) Uani 1 1 d .
C13 C 0.90083(16) 0.77933(19) 0.57331(13) 0.0299(4) Uani 1 1 d .
C14 C 0.86775(17) 0.7486(2) 0.46914(12) 0.0311(4) Uani 1 1 d .
H14 H 0.8619 0.8176 0.4206 0.037 Uiso 1 1 calc R
C15 C 0.84375(16) 0.61866(19) 0.43717(12) 0.0291(4) Uani 1 1 d .
H15 H 0.821 0.599 0.3662 0.035 Uiso 1 1 calc R
C16 C 0.85194(16) 0.51458(19) 0.50647(12) 0.0269(4) Uani 1 1 d .
C17 C 0.88845(17) 0.54713(19) 0.61118(12) 0.0299(4) Uani 1 1 d .
H17 H 0.8973 0.4778 0.66 0.036 Uiso 1 1 calc R
C18 C 0.91172(16) 0.6774(2) 0.64439(12) 0.0312(4) Uani 1 1 d .
H18 H 0.935 0.6976 0.7153 0.037 Uiso 1 1 calc R
C19 C 0.82722(16) 0.37570(19) 0.47466(12) 0.0279(4) Uani 1 1 d .
H19 H 0.8582 0.3096 0.526 0.033 Uiso 1 1 calc R
C20 C 0.76484(16) 0.33196(19) 0.37965(12) 0.0278(4) Uani 1 1 d .
H20 H 0.7312 0.3944 0.326 0.033 Uiso 1 1 calc R
C21 C 0.74866(16) 0.19048(19) 0.35880(13) 0.0293(4) Uani 1 1 d .
H21 H 0.7903 0.1334 0.4144 0.035 Uiso 1 1 calc R
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 0.0541(4) 0.0238(3) 0.0404(3) 0.0057(2) 0.0015(2) 0.0036(2)
N1 0.0552(12) 0.0416(11) 0.0283(8) 0.0008(8) 0.0029(8) 0.0053(9)
C2 0.0393(11) 0.0282(11) 0.0254(9) -0.0036(8) 0.0075(8) 0.0025(9)
C3 0.0296(10) 0.0277(10) 0.0227(8) -0.0028(7) 0.0070(7) 0.0059(8)
C4 0.0383(11) 0.0253(10) 0.0244(8) -0.0015(7) 0.0113(8) -0.0014(8)
C5 0.0287(10) 0.0268(10) 0.0253(8) -0.0037(7) 0.0063(7) -0.0009(8)
C6 0.0271(10) 0.0249(10) 0.0250(8) -0.0023(7) 0.0074(7) 0.0058(8)
C7 0.0317(10) 0.0274(10) 0.0308(9) 0.0021(8) 0.0084(8) -0.0020(8)
C8 0.0268(10) 0.0334(11) 0.0283(9) -0.0029(8) 0.0047(8) -0.0009(9)
C9 0.0308(10) 0.0233(10) 0.0290(9) 0.0040(7) 0.0064(8) 0.0041(8)
N11 0.0490(11) 0.0379(11) 0.0407(9) -0.0025(8) 0.0071(8) 0.0004(9)
C12 0.0301(11) 0.0386(12) 0.0286(9) 0.0008(9) 0.0023(8) 0.0036(9)
C13 0.0237(10) 0.0323(11) 0.0299(9) 0.0005(8) 0.0030(8) 0.0020(8)
C14 0.0298(10) 0.0334(11) 0.0251(9) 0.0057(8) 0.0014(7) 0.0034(9)
C15 0.0269(10) 0.0355(11) 0.0200(8) 0.0014(8) 0.0006(7) 0.0017(9)
C16 0.0206(9) 0.0333(11) 0.0233(8) -0.0011(8) 0.0021(7) 0.0025(8)
C17 0.0281(10) 0.0355(11) 0.0231(8) 0.0059(8) 0.0037(7) 0.0026(9)
C18 0.0301(10) 0.0378(11) 0.0219(8) -0.0003(8) 0.0030(8) 0.0013(9)
C19 0.0249(9) 0.0300(11) 0.0261(8) 0.0054(8) 0.0043(7) 0.0015(8)
C20 0.0256(10) 0.0305(11) 0.0260(9) 0.0025(8) 0.0063(7) 0.0030(8)
C21 0.0285(10) 0.0298(11) 0.0276(9) 0.0071(8) 0.0059(8) 0.0053(8)
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'
N N 0.0061 0.0033 '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
N1 C2 C3 178.24(19)
C8 C3 C4 120.31(15)
C8 C3 C2 118.83(16)
C4 C3 C2 120.85(17)
C5 C4 C3 119.64(17)
C5 C4 H4 120.2
C3 C4 H4 120.2
C4 C5 C6 120.62(16)
C4 C5 H5 119.7
C6 C5 H5 119.7
C5 C6 C7 119.02(15)
C5 C6 C9 120.75(15)
C7 C6 C9 120.21(16)
C8 C7 C6 120.55(17)
C8 C7 H7 119.7
C6 C7 H7 119.7
C7 C8 C3 119.84(16)
C7 C8 H8 120.1
C3 C8 H8 120.1
C21 C9 C6 129.30(17)
C21 C9 Cl1 116.76(13)
C6 C9 Cl1 113.92(12)
N11 C12 C13 177.8(2)
C18 C13 C14 119.80(18)
C18 C13 C12 121.36(16)
C14 C13 C12 118.84(17)
C15 C14 C13 119.96(17)
C15 C14 H14 120
C13 C14 H14 120
C14 C15 C16 121.57(16)
C14 C15 H15 119.2
C16 C15 H15 119.2
C15 C16 C17 117.62(17)
C15 C16 C19 122.72(15)
C17 C16 C19 119.65(16)
C18 C17 C16 121.45(17)
C18 C17 H17 119.3
C16 C17 H17 119.3
C17 C18 C13 119.58(16)
C17 C18 H18 120.2
C13 C18 H18 120.2
C20 C19 C16 126.35(16)
C20 C19 H19 116.8
C16 C19 H19 116.8
C19 C20 C21 120.36(16)
C19 C20 H20 119.8
C21 C20 H20 119.8
C9 C21 C20 128.91(16)
C9 C21 H21 115.5
C20 C21 H21 115.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C9 1.7529(19)
N1 C2 1.139(2)
C2 C3 1.447(2)
C3 C8 1.386(3)
C3 C4 1.391(2)
C4 C5 1.385(2)
C4 H4 0.95
C5 C6 1.390(2)
C5 H5 0.95
C6 C7 1.399(2)
C6 C9 1.479(2)
C7 C8 1.381(2)
C7 H7 0.95
C8 H8 0.95
C9 C21 1.347(2)
N11 C12 1.146(2)
C12 C13 1.441(3)
C13 C18 1.393(2)
C13 C14 1.399(2)
C14 C15 1.372(3)
C14 H14 0.95
C15 C16 1.397(2)
C15 H15 0.95
C16 C17 1.408(2)
C16 C19 1.458(3)
C17 C18 1.380(3)
C17 H17 0.95
C18 H18 0.95
C19 C20 1.346(2)
C19 H19 0.95
C20 C21 1.445(2)
C20 H20 0.95
C21 H21 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
C8 C3 C4 C5 0.4(3)
C2 C3 C4 C5 -179.70(16)
C3 C4 C5 C6 -1.6(3)
C4 C5 C6 C7 1.9(3)
C4 C5 C6 C9 179.91(16)
C5 C6 C7 C8 -1.0(3)
C9 C6 C7 C8 -179.02(16)
C6 C7 C8 C3 -0.2(3)
C4 C3 C8 C7 0.5(3)
C2 C3 C8 C7 -179.41(16)
C5 C6 C9 C21 36.6(3)
C7 C6 C9 C21 -145.42(19)
C5 C6 C9 Cl1 -144.89(15)
C7 C6 C9 Cl1 33.1(2)
C18 C13 C14 C15 1.3(3)
C12 C13 C14 C15 -179.02(17)
C13 C14 C15 C16 -0.3(3)
C14 C15 C16 C17 -1.3(3)
C14 C15 C16 C19 -179.87(16)
C15 C16 C17 C18 1.9(3)
C19 C16 C17 C18 -179.47(16)
C16 C17 C18 C13 -1.0(3)
C14 C13 C18 C17 -0.7(3)
C12 C13 C18 C17 179.63(17)
C15 C16 C19 C20 -17.8(3)
C17 C16 C19 C20 163.67(17)
C16 C19 C20 C21 179.22(16)
C6 C9 C21 C20 5.5(3)
Cl1 C9 C21 C20 -173.03(15)
C19 C20 C21 C9 175.15(18)