#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/21/4112191.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_4112191
loop_
_publ_author_name
'Hideki Amii'
'Lidija Vranicar'
'Heinz Gornitzka'
'Didier Bourissou'
'Guy Bertrand'
_publ_section_title
;
 Radical-Type Reactivity of the
 1,3-Dibora-2,4-Diphosphoniocyclobutane-1,3-diyl
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1344
_journal_page_last               1345
_journal_paper_doi               10.1021/ja039920i
_journal_volume                  126
_journal_year                    2004
_chemical_formula_sum            'C20.5 H46 B2 Br Cl P2'
_chemical_formula_weight         491.49
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/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                 110.408(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.684(2)
_cell_length_b                   10.1828(11)
_cell_length_c                   14.0169(16)
_cell_measurement_reflns_used    7146
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.449
_cell_measurement_theta_min      2.284
_cell_volume                     2633.2(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker CCD detector'
_diffrn_measurement_method       'phi and 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  0.0294
_diffrn_reflns_av_sigmaI/netI    0.0311
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11658
_diffrn_reflns_theta_full        23.25
_diffrn_reflns_theta_max         23.25
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    1.789
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.816885
_exptl_absorpt_correction_type   semi-empirical
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_description       block
_exptl_crystal_F_000             1044
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.5
_refine_diff_density_max         1.267
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3786
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0301
_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)+(0.0338P)²+2.5428P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0720
_refine_ls_wR_factor_ref         0.0761
_reflns_number_gt                3283
_reflns_number_total             3786
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja039920isi20031203_074816.cif
_cod_data_source_block           4
_cod_original_formula_sum        'C20.50 H46 B2 Br Cl P2'
_cod_database_code               4112191
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, 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
P1 P 0.30042(4) 0.88794(6) 0.24391(5) 0.01904(17) Uani 1 1 d .
C1 C 0.30589(15) 0.8828(3) 0.11409(19) 0.0237(6) Uani 1 1 d .
H1 H 0.2907 0.9721 0.0846 0.028 Uiso 1 1 calc R
C2 C 0.25073(17) 0.7877(3) 0.0441(2) 0.0337(7) Uani 1 1 d .
H2A H 0.2492 0.7994 -0.0260 0.051 Uiso 1 1 calc R
H2B H 0.2027 0.8055 0.0475 0.051 Uiso 1 1 calc R
H2C H 0.2650 0.6973 0.0660 0.051 Uiso 1 1 calc R
C3 C 0.38124(17) 0.8616(3) 0.1094(2) 0.0348(7) Uani 1 1 d .
H3A H 0.3993 0.7750 0.1373 0.052 Uiso 1 1 calc R
H3B H 0.4141 0.9297 0.1495 0.052 Uiso 1 1 calc R
H3C H 0.3788 0.8666 0.0385 0.052 Uiso 1 1 calc R
C4 C 0.35025(15) 1.0377(3) 0.3082(2) 0.0268(6) Uani 1 1 d .
H4 H 0.3354 1.0519 0.3687 0.032 Uiso 1 1 calc R
C5 C 0.32896(18) 1.1629(3) 0.2453(2) 0.0376(8) Uani 1 1 d .
H5A H 0.3531 1.2382 0.2868 0.056 Uiso 1 1 calc R
H5B H 0.2763 1.1746 0.2231 0.056 Uiso 1 1 calc R
H5C H 0.3438 1.1563 0.1856 0.056 Uiso 1 1 calc R
C6 C 0.43321(16) 1.0249(3) 0.3509(2) 0.0391(8) Uani 1 1 d .
H6A H 0.4518 1.0208 0.2946 0.059 Uiso 1 1 calc R
H6B H 0.4467 0.9445 0.3917 0.059 Uiso 1 1 calc R
H6C H 0.4541 1.1011 0.3938 0.059 Uiso 1 1 calc R
B1 B 0.32170(17) 0.7261(3) 0.3369(2) 0.0204(7) Uani 1 1 d .
C7 C 0.37955(15) 0.6108(3) 0.3393(2) 0.0237(6) Uani 1 1 d .
C8 C 0.36080(16) 0.5359(3) 0.2373(2) 0.0281(6) Uani 1 1 d .
H8A H 0.4004 0.4755 0.2408 0.042 Uiso 1 1 calc R
H8B H 0.3542 0.5988 0.1818 0.042 Uiso 1 1 calc R
H8C H 0.3160 0.4859 0.2246 0.042 Uiso 1 1 calc R
C9 C 0.45631(15) 0.6688(3) 0.3637(2) 0.0319(7) Uani 1 1 d .
H9A H 0.4902 0.5983 0.3638 0.048 Uiso 1 1 calc R
H9B H 0.4718 0.7108 0.4308 0.048 Uiso 1 1 calc R
H9C H 0.4555 0.7341 0.3120 0.048 Uiso 1 1 calc R
C10 C 0.38523(16) 0.5069(3) 0.4223(2) 0.0333(7) Uani 1 1 d .
H10A H 0.3379 0.4649 0.4083 0.050 Uiso 1 1 calc R
H10B H 0.4002 0.5497 0.4891 0.050 Uiso 1 1 calc R
H10C H 0.4211 0.4403 0.4221 0.050 Uiso 1 1 calc R
Br1 Br 0.351293(16) 0.81163(3) 0.480750(19) 0.02974(11) Uani 1 1 d .
P2 P 0.21243(4) 0.70518(6) 0.29716(5) 0.01815(16) Uani 1 1 d .
C11 C 0.17585(14) 0.5698(2) 0.2041(2) 0.0233(6) Uani 1 1 d .
H11 H 0.2084 0.5654 0.1631 0.028 Uiso 1 1 calc R
C12 C 0.09977(16) 0.5944(3) 0.1270(2) 0.0323(7) Uani 1 1 d .
H12A H 0.0867 0.5234 0.0767 0.048 Uiso 1 1 calc R
H12B H 0.0991 0.6784 0.0925 0.048 Uiso 1 1 calc R
H12C H 0.0648 0.5973 0.1626 0.048 Uiso 1 1 calc R
C13 C 0.18010(16) 0.4337(3) 0.2526(2) 0.0312(7) Uani 1 1 d .
H13A H 0.1449 0.4283 0.2876 0.047 Uiso 1 1 calc R
H13B H 0.2290 0.4195 0.3017 0.047 Uiso 1 1 calc R
H13C H 0.1691 0.3663 0.1994 0.047 Uiso 1 1 calc R
C14 C 0.17966(15) 0.6900(3) 0.4058(2) 0.0245(6) Uani 1 1 d .
H14 H 0.1935 0.7742 0.4445 0.029 Uiso 1 1 calc R
C15 C 0.09729(16) 0.6821(3) 0.3739(2) 0.0327(7) Uani 1 1 d .
H15A H 0.0803 0.5995 0.3375 0.049 Uiso 1 1 calc R
H15B H 0.0753 0.7561 0.3291 0.049 Uiso 1 1 calc R
H15C H 0.0834 0.6855 0.4345 0.049 Uiso 1 1 calc R
C16 C 0.21573(17) 0.5814(3) 0.4824(2) 0.0341(7) Uani 1 1 d .
H16A H 0.2030 0.5924 0.5436 0.051 Uiso 1 1 calc R
H16B H 0.2685 0.5869 0.5009 0.051 Uiso 1 1 calc R
H16C H 0.1988 0.4955 0.4518 0.051 Uiso 1 1 calc R
B2 B 0.19935(17) 0.8834(3) 0.2388(2) 0.0206(7) Uani 1 1 d .
C17 C 0.13035(16) 0.9627(3) 0.1663(2) 0.0305(7) Uani 1 1 d .
C18 C 0.16672(18) 1.0013(3) 0.2849(3) 0.0439(9) Uani 1 1 d .
H18A H 0.1949 1.0840 0.3019 0.053 Uiso 1 1 calc R
H18B H 0.1399 0.9787 0.3307 0.053 Uiso 1 1 calc R
C19 C 0.13861(17) 1.0597(3) 0.0895(2) 0.0379(8) Uani 1 1 d .
H19A H 0.1280 1.0159 0.0237 0.057 Uiso 1 1 calc R
H19B H 0.1884 1.0933 0.1129 0.057 Uiso 1 1 calc R
H19C H 0.1048 1.1328 0.0822 0.057 Uiso 1 1 calc R
C20 C 0.05440(16) 0.9131(3) 0.1356(2) 0.0313(7) Uani 1 1 d .
H20A H 0.0213 0.9872 0.1292 0.047 Uiso 1 1 calc R
H20B H 0.0503 0.8519 0.1872 0.047 Uiso 1 1 calc R
H20C H 0.0417 0.8678 0.0700 0.047 Uiso 1 1 calc R
Cl1 Cl 0.02670(6) 0.30265(9) 0.36105(7) 0.0573(3) Uani 1 1 d .
C21 C 0.0000 0.2079(5) 0.2500 0.0527(14) Uani 1 2 d S
H21A H -0.0408 0.1506 0.2493 0.063 Uiso 0.50 1 calc PR
H21B H 0.0408 0.1506 0.2507 0.063 Uiso 0.50 1 calc PR
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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'
Br Br -0.2901 2.4595 '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
C1 P1 C4 107.14(12) .
C1 P1 B2 111.52(12) .
C4 P1 B2 113.06(13) .
C1 P1 B1 122.03(12) .
C4 P1 B1 113.16(12) .
B2 P1 B1 89.07(12) .
C3 C1 C2 111.5(2) .
C3 C1 P1 115.82(19) .
C2 C1 P1 112.00(19) .
C5 C4 C6 109.7(2) .
C5 C4 P1 114.4(2) .
C6 C4 P1 115.3(2) .
C7 B1 P2 126.49(19) .
C7 B1 P1 125.32(19) .
P2 B1 P1 87.01(12) .
C7 B1 Br1 108.94(18) .
P2 B1 Br1 102.77(13) .
P1 B1 Br1 101.84(12) .
C9 C7 C8 107.1(2) .
C9 C7 C10 106.6(2) .
C8 C7 C10 106.8(2) .
C9 C7 B1 110.6(2) .
C8 C7 B1 113.4(2) .
C10 C7 B1 112.0(2) .
C14 P2 C11 110.68(12) .
C14 P2 B2 112.62(12) .
C11 P2 B2 115.38(12) .
C14 P2 B1 114.85(12) .
C11 P2 B1 112.52(12) .
B2 P2 B1 89.43(12) .
C12 C11 C13 110.4(2) .
C12 C11 P2 114.68(18) .
C13 C11 P2 114.29(18) .
C15 C14 C16 110.6(2) .
C15 C14 P2 113.68(19) .
C16 C14 P2 115.25(19) .
C18 B2 C17 60.5(2) .
C18 B2 P1 120.7(2) .
C17 B2 P1 129.4(2) .
C18 B2 P2 122.5(2) .
C17 B2 P2 133.4(2) .
P1 B2 P2 91.29(13) .
C20 C17 C19 111.2(2) .
C20 C17 B2 123.7(2) .
C19 C17 B2 120.2(2) .
C20 C17 C18 114.8(2) .
C19 C17 C18 117.1(2) .
B2 C17 C18 59.70(18) .
B2 C18 C17 59.84(18) .
Cl1 C21 Cl1 113.1(3) 2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 C1 1.861(3) .
P1 C4 1.866(3) .
P1 B2 1.966(3) .
P1 B1 2.052(3) .
C1 C3 1.523(4) .
C1 C2 1.528(4) .
C4 C5 1.522(4) .
C4 C6 1.536(4) .
B1 C7 1.628(4) .
B1 P2 2.036(3) .
B1 Br1 2.084(3) .
C7 C9 1.545(4) .
C7 C8 1.547(4) .
C7 C10 1.548(4) .
P2 C14 1.856(3) .
P2 C11 1.861(3) .
P2 B2 1.970(3) .
C11 C12 1.531(4) .
C11 C13 1.533(4) .
C14 C15 1.526(4) .
C14 C16 1.533(4) .
B2 C18 1.600(4) .
B2 C17 1.602(4) .
C17 C20 1.492(4) .
C17 C19 1.510(4) .
C17 C18 1.612(5) .
Cl1 C21 1.749(3) .
C21 Cl1 1.749(3) 2
