#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:27:53 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178391 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/13/4021382.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_4021382
loop_
_publ_author_name
'V. Zaitsev'
'S. V. Rosokha'
'M. Head-Gordon'
'J. K. Kochi'
_publ_section_title
;
 Steric Modulations in the Reversible Dimerizations of Phenalenyl
 Radicals via Unusually Weak Carbon-Centered π- and σ-Bonds
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              520
_journal_page_last               526
_journal_paper_doi               10.1021/jo051612a
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C46 H54 Cl4'
_chemical_formula_weight         748.69
_chemical_name_systematic
;
  1,2-bis(3,8-di-t-butylphenalen-1-ylidene)etane
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 113.023(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.9777(9)
_cell_length_b                   15.4966(12)
_cell_length_c                   11.5901(9)
_cell_measurement_reflns_used    1399
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      20.88
_cell_measurement_theta_min      2.27
_cell_volume                     1979.9(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measurement_device       'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1241
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6380
_diffrn_reflns_theta_max         31.85
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    0.331
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_F_000             796
_refine_diff_density_max         0.688
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.017
_refine_ls_goodness_of_fit_obs   1.183
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         6366
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_restrained_S_obs      1.183
_refine_ls_R_factor_all          0.2162
_refine_ls_R_factor_obs          0.0879
_refine_ls_shift/esd_max         -0.251
_refine_ls_shift/esd_mean        0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1181P)²+0.2153P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2747
_refine_ls_wR_factor_obs         0.1949
_reflns_number_observed          2513
_reflns_number_total             6380
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            jo051612asi20050803_090046.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1181P)^2^+0.2153P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.1181P)^2^+0.2153P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4021382
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
Cl1 Cl 0.0196(2) 0.61093(9) 0.4398(2) 0.0799(6) Uani 0.860(4) d P 1
Cl2 Cl 0.1248(2) 0.47465(10) 0.3441(2) 0.0860(7) Uani 0.860(4) d P 1
C1X C 0.1467(5) 0.5443(4) 0.4652(5) 0.066(2) Uani 0.860(4) d P 1
H1XA H 0.2179(5) 0.5811(4) 0.4771(5) 0.080 Uiso 0.860(4) calc PR 1
H1XB H 0.1648(5) 0.5107(4) 0.5431(5) 0.080 Uiso 0.860(4) calc PR 1
C1 C 0.3914(3) 0.1865(2) 0.2392(3) 0.0299(7) Uani 1 d . .
C2 C 0.3048(3) 0.2231(2) 0.1303(3) 0.0327(8) Uani 1 d . .
C3 C 0.2732(3) 0.3090(2) 0.1234(3) 0.0301(7) Uani 1 d . .
C4 C 0.3325(3) 0.3593(2) 0.2307(3) 0.0301(8) Uani 1 d . .
C5 C 0.4893(3) 0.3827(2) 0.4497(3) 0.0280(7) Uani 1 d . .
C6 C 0.5809(3) 0.3411(2) 0.5560(3) 0.0284(7) Uani 1 d . .
C7 C 0.6108(3) 0.2562(2) 0.5631(3) 0.0257(7) Uani 1 d . .
C8 C 0.5450(3) 0.2007(2) 0.4562(3) 0.0275(7) Uani 1 d . .
C9 C 0.4528(3) 0.2385(2) 0.3471(3) 0.0255(7) Uani 1 d . .
C10 C 0.4223(3) 0.3281(2) 0.3406(3) 0.0261(7) Uani 1 d . .
C11 C 0.5662(3) 0.1122(2) 0.4534(4) 0.0342(8) Uani 1 d . .
C12 C 0.5034(3) 0.0620(2) 0.3476(4) 0.0352(8) Uani 1 d . .
C13 C 0.4198(3) 0.0967(2) 0.2426(4) 0.0345(8) Uani 1 d . .
C14 C 0.1767(3) 0.3486(2) 0.0060(3) 0.0351(8) Uani 1 d . .
C15 C 0.2276(4) 0.4282(3) -0.0355(4) 0.0596(13) Uani 1 d . .
H15A H 0.3006(16) 0.4120(5) -0.0490(27) 0.089 Uiso 1 calc R .
H15B H 0.2481(25) 0.4726(8) 0.0297(13) 0.089 Uiso 1 calc R .
H15C H 0.1665(11) 0.4508(12) -0.1137(15) 0.089 Uiso 1 calc R .
C16 C 0.0680(3) 0.3757(3) 0.0371(4) 0.0559(11) Uani 1 d . .
H16A H 0.0393(17) 0.3260(6) 0.0701(26) 0.084 Uiso 1 calc R .
H16B H 0.0024(10) 0.3968(18) -0.0391(7) 0.084 Uiso 1 calc R .
H16C H 0.0930(8) 0.4218(13) 0.1001(21) 0.084 Uiso 1 calc R .
C17 C 0.1320(4) 0.2857(2) -0.1045(4) 0.0488(10) Uani 1 d . .
H17A H 0.0940(21) 0.2357(8) -0.0828(10) 0.073 Uiso 1 calc R .
H17B H 0.2009(5) 0.2665(13) -0.1236(16) 0.073 Uiso 1 calc R .
H17C H 0.0725(18) 0.3147(6) -0.1780(8) 0.073 Uiso 1 calc R .
C18 C 0.7141(3) 0.2217(2) 0.6822(3) 0.0314(7) Uani 1 d . .
C19 C 0.8210(3) 0.1890(2) 0.6497(4) 0.0396(9) Uani 1 d . .
H19A H 0.8538(14) 0.2371(4) 0.6178(21) 0.059 Uiso 1 calc R .
H19B H 0.7919(5) 0.1438(11) 0.5857(16) 0.059 Uiso 1 calc R .
H19C H 0.8848(10) 0.1654(14) 0.7253(6) 0.059 Uiso 1 calc R .
C20 C 0.6684(3) 0.1490(2) 0.7446(4) 0.0420(9) Uani 1 d . .
H20A H 0.5825(7) 0.1583(9) 0.7275(20) 0.063 Uiso 1 calc R .
H20B H 0.7155(15) 0.1496(10) 0.8354(4) 0.063 Uiso 1 calc R .
H20C H 0.6784(21) 0.0930(3) 0.7105(17) 0.063 Uiso 1 calc R .
C21 C 0.7666(3) 0.2919(2) 0.7823(4) 0.0422(9) Uani 1 d . .
H21A H 0.7980(20) 0.3394(8) 0.7478(8) 0.063 Uiso 1 calc R .
H21B H 0.8327(15) 0.2675(5) 0.8553(10) 0.063 Uiso 1 calc R .
H21C H 0.7028(6) 0.3136(11) 0.8078(17) 0.063 Uiso 1 calc R .
C22 C 0.4699(3) 0.4710(2) 0.4509(3) 0.0287(7) Uani 1 d . .
H2 H 0.2651(30) 0.1886(23) 0.0595(35) 0.036(9) Uiso 1 d . .
H4 H 0.3152(27) 0.4160(21) 0.2314(30) 0.026(8) Uiso 1 d . .
H6 H 0.6205(28) 0.3769(20) 0.6269(33) 0.029(9) Uiso 1 d . .
H11 H 0.6253(29) 0.0846(21) 0.5337(33) 0.031(9) Uiso 1 d . .
H12 H 0.5224(30) 0.0060(23) 0.3508(33) 0.037(9) Uiso 1 d . .
H13 H 0.3767(30) 0.0616(22) 0.1705(35) 0.038(10) Uiso 1 d . .
H22 H 0.4140(27) 0.4955(18) 0.3764(30) 0.020(8) Uiso 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 0.0033 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_3
Cl2 C1X Cl1 112.8(3) .
C2 C1 C9 120.5(3) .
C2 C1 C13 120.2(3) .
C9 C1 C13 119.3(3) .
C3 C2 C1 122.2(3) .
C2 C3 C4 117.0(3) .
C2 C3 C14 122.3(3) .
C4 C3 C14 120.8(3) .
C10 C4 C3 124.0(3) .
C22 C5 C6 120.4(3) .
C22 C5 C10 122.5(3) .
C6 C5 C10 117.0(3) .
C7 C6 C5 125.4(3) .
C6 C7 C8 118.5(3) .
C6 C7 C18 119.3(3) .
C8 C7 C18 122.2(2) .
C11 C8 C9 117.6(3) .
C11 C8 C7 123.7(3) .
C9 C8 C7 118.7(2) .
C1 C9 C10 117.9(3) .
C1 C9 C8 119.7(3) .
C10 C9 C8 122.3(3) .
C4 C10 C9 118.4(3) .
C4 C10 C5 123.5(3) .
C9 C10 C5 118.1(3) .
C8 C11 C12 121.8(3) .
C13 C12 C11 121.7(3) .
C12 C13 C1 119.8(3) .
C17 C14 C3 112.7(3) .
C17 C14 C15 107.5(3) .
C3 C14 C15 110.3(3) .
C17 C14 C16 108.6(3) .
C3 C14 C16 108.4(3) .
C15 C14 C16 109.2(3) .
C21 C18 C7 112.3(3) .
C21 C18 C20 106.1(3) .
C7 C18 C20 111.3(3) .
C21 C18 C19 106.3(3) .
C7 C18 C19 110.2(3) .
C20 C18 C19 110.5(3) .
C5 C22 C22 127.0(4) 3_666
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C1X 1.766(6) .
Cl2 C1X 1.707(6) .
C1 C2 1.402(5) .
C1 C9 1.427(4) .
C1 C13 1.429(4) .
C2 C3 1.379(4) .
C3 C4 1.403(5) .
C3 C14 1.527(5) .
C4 C10 1.393(5) .
C5 C22 1.390(4) .
C5 C6 1.442(4) .
C5 C10 1.471(4) .
C6 C7 1.357(4) .
C7 C8 1.460(4) .
C7 C18 1.544(4) .
C8 C11 1.397(4) .
C8 C9 1.438(4) .
C9 C10 1.431(4) .
C11 C12 1.398(5) .
C12 C13 1.349(5) .
C14 C17 1.530(5) .
C14 C15 1.534(5) .
C14 C16 1.539(5) .
C18 C21 1.535(5) .
C18 C20 1.550(5) .
C18 C19 1.554(5) .
C22 C22 1.407(6) 3_666
