#------------------------------------------------------------------------------
#$Date: 2015-09-25 16:16:23 +0300 (Fri, 25 Sep 2015) $
#$Revision: 158310 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/78/7117858.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_7117858
loop_
_publ_author_name
'Dominik Wendinger'
'Johanna A. Januszewski'
'Frank Hampel'
'Rik R. Tykwinski'
_publ_section_title
;
 Thermal dimerization of [n]cumulenes (n = 5, 7, 9)
;
_journal_name_full               Chem.Commun.
_journal_page_first              14877
_journal_paper_doi               10.1039/C5cc05679a
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C72 H56, 2(C H2 Cl2)'
_chemical_formula_sum            'C74 H60 Cl4'
_chemical_formula_weight         1091.02
_chemical_name_systematic
;
 ? 
;
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-04-12
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_audit_update_record
;
2015-05-26 deposited with the CCDC.
2015-08-07 downloaded from the CCDC.
;
_cell_angle_alpha                104.011(5)
_cell_angle_beta                 90.739(4)
_cell_angle_gamma                104.207(4)
_cell_formula_units_Z            1
_cell_length_a                   9.7822(5)
_cell_length_b                   12.5174(6)
_cell_length_c                   12.6361(8)
_cell_measurement_reflns_used    4130
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      61.8770
_cell_measurement_theta_min      3.7550
_cell_volume                     1451.01(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      173.000(10)
_diffrn_detector_area_resol_mean 10.6144
_diffrn_measured_fraction_theta_full 0.9837
_diffrn_measured_fraction_theta_max 0.9527
_diffrn_measurement_details
;
  1 omega  -86.00  -34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  -30.0000 52

  2 omega  -26.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -150.0000 98

  3 omega    7.00   42.00   1.0000    2.7900
omega____ theta____ kappa____ phi______ frames
    -       82.7293  -30.0000 -150.0000 35

  4 omega   23.00  122.00   1.0000    2.7900
omega____ theta____ kappa____ phi______ frames
    -       82.7293 -125.0000  -30.0000 99

  5 omega   57.00  155.00   1.0000    2.7900
omega____ theta____ kappa____ phi______ frames
    -       82.7293   30.0000 -150.0000 98

  6 omega   54.00  149.00   1.0000    2.7900
omega____ theta____ kappa____ phi______ frames
    -       82.7293   30.0000  120.0000 95

  7 omega   10.00   99.00   1.0000    2.7900
omega____ theta____ kappa____ phi______ frames
    -       82.7293  -45.0000  -60.0000 89

  8 omega   56.00   98.00   1.0000    2.7900
omega____ theta____ kappa____ phi______ frames
    -       82.7293 -125.0000  120.0000 42

  9 omega   19.00  115.00   1.0000    2.7900
omega____ theta____ kappa____ phi______ frames
    -       82.7293  -77.0000  120.0000 96
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0620895000
_diffrn_orient_matrix_UB_12      -0.1021834000
_diffrn_orient_matrix_UB_13      -0.0460138000
_diffrn_orient_matrix_UB_21      -0.0545971000
_diffrn_orient_matrix_UB_22      -0.0052352000
_diffrn_orient_matrix_UB_23      -0.1165242000
_diffrn_orient_matrix_UB_31      0.1404025000
_diffrn_orient_matrix_UB_32      0.0821681000
_diffrn_orient_matrix_UB_33      -0.0137175000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6450
_diffrn_reflns_theta_full        61.96
_diffrn_reflns_theta_max         61.96
_diffrn_reflns_theta_min         3.77
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.181
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81730
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             572
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_exptl_crystal_size_max          0.2648
_exptl_crystal_size_mid          0.1574
_exptl_crystal_size_min          0.1046
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         4350
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0529
_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)+(0.0812P)²+0.6294P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1402
_refine_ls_wR_factor_ref         0.1474
_reflns_number_gt                3828
_reflns_number_total             4350
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc05679a2.cif
_cod_data_source_block           dw07
_cod_original_cell_volume        1451.00(14)
_cod_database_code               7117858
_chemical_oxdiff_formula         'C36 H28'
_reflns_odcompleteness_completeness 98.37
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     58.86
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0570(2) 0.42432(18) 0.31266(17) 0.0249(5) Uani 1 1 d . . .
C2 C 0.1830(2) 0.44300(18) 0.36168(17) 0.0260(5) Uani 1 1 d . . .
C3 C 0.3075(2) 0.45270(17) 0.40994(17) 0.0240(5) Uani 1 1 d . . .
C4 C 0.3662(2) 0.53069(18) 0.51220(17) 0.0251(5) Uani 1 1 d . . .
C5 C 0.4561(2) 0.58266(18) 0.58501(17) 0.0253(5) Uani 1 1 d . . .
C6 C 0.5940(2) 0.61989(17) 0.64109(17) 0.0244(5) Uani 1 1 d . . .
C7 C 0.6394(2) 0.71017(18) 0.72335(18) 0.0270(5) Uani 1 1 d . . .
C8 C 0.6966(2) 0.80406(17) 0.79822(17) 0.0242(5) Uani 1 1 d . . .
C11 C -0.0586(2) 0.33297(18) 0.33793(18) 0.0280(5) Uani 1 1 d . . .
C12 C -0.0798(3) 0.3334(2) 0.4476(2) 0.0376(6) Uani 1 1 d . . .
H12 H -0.0229 0.3928 0.5041 0.045 Uiso 1 1 calc R . .
C13 C -0.1816(3) 0.2490(3) 0.4746(3) 0.0507(7) Uani 1 1 d . . .
H13 H -0.1971 0.2512 0.5491 0.061 Uiso 1 1 calc R . .
C14 C -0.2608(3) 0.1614(2) 0.3924(3) 0.0549(8) Uani 1 1 d . . .
H14 H -0.3303 0.1022 0.4105 0.066 Uiso 1 1 calc R . .
C15 C -0.2403(3) 0.1585(2) 0.2841(3) 0.0495(7) Uani 1 1 d . . .
H15 H -0.2960 0.0971 0.2288 0.059 Uiso 1 1 calc R . .
C16 C -0.1388(2) 0.2444(2) 0.2538(2) 0.0362(6) Uani 1 1 d . . .
C17 C -0.1137(3) 0.2355(2) 0.1362(2) 0.0468(7) Uani 1 1 d . . .
H17A H -0.1557 0.2888 0.1102 0.070 Uiso 1 1 calc R . .
H17B H -0.1572 0.1576 0.0932 0.070 Uiso 1 1 calc R . .
H17C H -0.0118 0.2542 0.1280 0.070 Uiso 1 1 calc R . .
C21 C 0.0242(2) 0.49529(17) 0.24144(17) 0.0262(5) Uani 1 1 d . . .
C22 C -0.1066(2) 0.5209(2) 0.24778(19) 0.0328(5) Uani 1 1 d . . .
H22 H -0.1715 0.4913 0.2953 0.039 Uiso 1 1 calc R . .
C23 C -0.1443(3) 0.5887(2) 0.1861(2) 0.0392(6) Uani 1 1 d . . .
H23 H -0.2339 0.6057 0.1914 0.047 Uiso 1 1 calc R . .
C24 C -0.0494(3) 0.6312(2) 0.1167(2) 0.0426(6) Uani 1 1 d . . .
H24 H -0.0730 0.6786 0.0748 0.051 Uiso 1 1 calc R . .
C25 C 0.0793(3) 0.6047(2) 0.1086(2) 0.0397(6) Uani 1 1 d . . .
H25 H 0.1422 0.6331 0.0594 0.048 Uiso 1 1 calc R . .
C26 C 0.1204(2) 0.53741(19) 0.17008(19) 0.0310(5) Uani 1 1 d . . .
C27 C 0.2611(3) 0.5100(2) 0.1552(2) 0.0432(6) Uani 1 1 d . . .
H27A H 0.3291 0.5589 0.2155 0.065 Uiso 1 1 calc R . .
H27B H 0.2951 0.5231 0.0857 0.065 Uiso 1 1 calc R . .
H27C H 0.2508 0.4299 0.1546 0.065 Uiso 1 1 calc R . .
C31 C 0.7021(2) 0.81266(17) 0.91790(17) 0.0253(5) Uani 1 1 d . . .
C32 C 0.8212(2) 0.88630(19) 0.98174(18) 0.0311(5) Uani 1 1 d . . .
H32 H 0.8929 0.9297 0.9479 0.037 Uiso 1 1 calc R . .
C33 C 0.8372(3) 0.8976(2) 1.09295(19) 0.0362(6) Uani 1 1 d . . .
H33 H 0.9195 0.9477 1.1350 0.043 Uiso 1 1 calc R . .
C34 C 0.7325(3) 0.8354(2) 1.14239(19) 0.0380(6) Uani 1 1 d . . .
H34 H 0.7424 0.8424 1.2188 0.046 Uiso 1 1 calc R . .
C35 C 0.6138(3) 0.7630(2) 1.08067(19) 0.0366(6) Uani 1 1 d . . .
H35 H 0.5425 0.7208 1.1158 0.044 Uiso 1 1 calc R . .
C36 C 0.5950(2) 0.74976(19) 0.96806(18) 0.0295(5) Uani 1 1 d . . .
C37 C 0.4610(3) 0.6703(2) 0.9058(2) 0.0472(7) Uani 1 1 d . . .
H37A H 0.4257 0.7061 0.8541 0.071 Uiso 1 1 calc R . .
H37B H 0.3894 0.6542 0.9573 0.071 Uiso 1 1 calc R . .
H37C H 0.4808 0.5989 0.8658 0.071 Uiso 1 1 calc R . .
C39 C 0.4025(3) 0.1710(3) 0.5229(2) 0.0564(8) Uani 1 1 d . . .
H39A H 0.4648 0.2115 0.4761 0.068 Uiso 1 1 calc R . .
H39B H 0.3440 0.0988 0.4753 0.068 Uiso 1 1 calc R . .
C41 C 0.7686(2) 0.90655(18) 0.75804(17) 0.0258(5) Uani 1 1 d . . .
C42 C 0.8738(2) 0.8956(2) 0.68596(18) 0.0322(5) Uani 1 1 d . . .
H42 H 0.8976 0.8248 0.6637 0.039 Uiso 1 1 calc R . .
C43 C 0.9443(3) 0.9867(2) 0.6461(2) 0.0435(6) Uani 1 1 d . . .
H43 H 1.0166 0.9784 0.5976 0.052 Uiso 1 1 calc R . .
C44 C 0.9088(3) 1.0885(2) 0.6773(2) 0.0490(7) Uani 1 1 d . . .
H44 H 0.9569 1.1514 0.6509 0.059 Uiso 1 1 calc R . .
C45 C 0.8028(3) 1.0996(2) 0.7474(2) 0.0475(7) Uani 1 1 d . . .
H45 H 0.7784 1.1703 0.7673 0.057 Uiso 1 1 calc R . .
C46 C 0.7302(2) 1.00972(19) 0.7899(2) 0.0352(6) Uani 1 1 d . . .
C47 C 0.6146(3) 1.0248(2) 0.8649(2) 0.0491(7) Uani 1 1 d . . .
H47A H 0.5392 0.9539 0.8496 0.074 Uiso 1 1 calc R . .
H47B H 0.5761 1.0865 0.8528 0.074 Uiso 1 1 calc R . .
H47C H 0.6530 1.0437 0.9410 0.074 Uiso 1 1 calc R . .
Cl1 Cl 0.50774(8) 0.13977(7) 0.61945(6) 0.0579(2) Uani 1 1 d . . .
Cl2 Cl 0.29193(10) 0.25467(7) 0.58386(6) 0.0657(3) Uani 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
6 -1 1 0.1085 6.2258 -0.8876 0.7445 0.4430 -0.4220 0.7910
0 7 -5 0.0649 0.2490 7.3235 -4.6501 -0.5189 0.4899 0.7005
-6 1 -1 0.1288 -6.2447 1.4286 -1.0892 -0.4836 0.4604 -0.7444
0 -7 5 0.0860 0.2561 -7.4418 4.7399 0.5582 -0.5273 -0.6405
2 0 7 0.0529 2.3195 0.4805 6.9281 -0.2239 -0.9364 0.2701
0 -1 8 0.0569 0.1083 -1.3831 8.1699 -0.2279 -0.9507 -0.2105
-1 1 -8 0.0476 -0.9061 0.7511 -7.9472 0.2327 0.9716 0.0435
6 -2 -3 0.1058 6.0366 -1.5803 -2.6239 0.6570 -0.0156 0.7537
0 -8 0 0.0738 0.2766 -7.7897 0.4033 0.7946 -0.0213 -0.6068
-6 1 3 0.1178 -6.0175 0.7930 2.6687 -0.5774 0.0134 -0.8163
1 7 -1 0.0615 0.9179 7.4248 -0.9190 -0.6594 0.0181 0.7516
1 0 -8 0.0608 0.8763 0.0243 -7.9465 0.4176 0.8780 0.2340
-1 -1 -7 0.0577 -0.7742 -1.3775 -7.2645 0.4270 0.8960 -0.1222
-5 -4 3 0.1235 -4.5753 -3.7703 3.1083 -0.0418 -0.0927 -0.9948
0 1 8 0.0575 -0.0125 0.7211 7.7130 -0.4294 -0.9018 -0.0483
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
C2 C1 C11 117.1(2) . .
C2 C1 C21 122.80(19) . .
C21 C1 C11 119.93(18) . .
C1 C2 C3 175.3(2) . .
C2 C3 C4 125.3(2) . .
C2 C3 C6 122.01(19) . 2_666
C4 C3 C6 112.70(17) . 2_666
C5 C4 C3 156.8(2) . .
C4 C5 C6 156.9(2) . .
C5 C6 C3 112.66(17) . 2_666
C7 C6 C3 121.28(19) . 2_666
C7 C6 C5 125.9(2) . .
C8 C7 C6 173.2(2) . .
C7 C8 C31 124.0(2) . .
C7 C8 C41 116.69(19) . .
C31 C8 C41 119.20(17) . .
C12 C11 C1 119.0(2) . .
C16 C11 C1 120.6(2) . .
C16 C11 C12 120.2(2) . .
C13 C12 C11 121.0(3) . .
C14 C13 C12 119.2(3) . .
C13 C14 C15 120.7(3) . .
C14 C15 C16 121.5(3) . .
C11 C16 C15 117.3(2) . .
C11 C16 C17 122.4(2) . .
C15 C16 C17 120.2(2) . .
C22 C21 C1 117.72(19) . .
C22 C21 C26 119.7(2) . .
C26 C21 C1 122.56(19) . .
C23 C22 C21 121.4(2) . .
C24 C23 C22 119.0(2) . .
C25 C24 C23 119.9(2) . .
C24 C25 C26 122.3(2) . .
C21 C26 C27 123.0(2) . .
C25 C26 C21 117.6(2) . .
C25 C26 C27 119.4(2) . .
C32 C31 C8 117.43(19) . .
C32 C31 C36 119.3(2) . .
C36 C31 C8 123.27(19) . .
C33 C32 C31 121.5(2) . .
C32 C33 C34 119.3(2) . .
C35 C34 C33 119.9(2) . .
C34 C35 C36 122.0(2) . .
C31 C36 C37 122.9(2) . .
C35 C36 C31 118.0(2) . .
C35 C36 C37 119.1(2) . .
Cl2 C39 Cl1 112.60(16) . .
C42 C41 C8 118.15(19) . .
C42 C41 C46 120.2(2) . .
C46 C41 C8 121.7(2) . .
C43 C42 C41 121.0(2) . .
C44 C43 C42 119.5(3) . .
C43 C44 C45 119.9(2) . .
C44 C45 C46 122.2(3) . .
C41 C46 C45 117.2(2) . .
C41 C46 C47 122.2(2) . .
C45 C46 C47 120.6(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.313(3) .
C1 C11 1.497(3) .
C1 C21 1.491(3) .
C2 C3 1.320(3) .
C3 C4 1.431(3) .
C3 C6 1.527(3) 2_666
C4 C5 1.204(3) .
C5 C6 1.431(3) .
C6 C3 1.527(3) 2_666
C6 C7 1.314(3) .
C7 C8 1.310(3) .
C8 C31 1.489(3) .
C8 C41 1.510(3) .
C11 C12 1.403(3) .
C11 C16 1.398(3) .
C12 C13 1.375(4) .
C13 C14 1.375(4) .
C14 C15 1.379(5) .
C15 C16 1.405(4) .
C16 C17 1.491(4) .
C21 C22 1.392(3) .
C21 C26 1.409(3) .
C22 C23 1.391(3) .
C23 C24 1.385(4) .
C24 C25 1.378(4) .
C25 C26 1.396(3) .
C26 C27 1.502(4) .
C31 C32 1.395(3) .
C31 C36 1.405(3) .
C32 C33 1.381(3) .
C33 C34 1.381(4) .
C34 C35 1.377(4) .
C35 C36 1.396(3) .
C36 C37 1.511(3) .
C39 Cl1 1.760(3) .
C39 Cl2 1.745(3) .
C41 C42 1.393(3) .
C41 C46 1.401(3) .
C42 C43 1.389(3) .
C43 C44 1.371(4) .
C44 C45 1.383(4) .
C45 C46 1.403(4) .
C46 C47 1.502(4) .
