#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:45:29 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178962 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/91/4119103.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_4119103
loop_
_publ_author_name
'Yamamoto, Yoshihiko'
'Ishii, Jun-ichi'
'Nishiyama, Hisao'
'Itoh, Kenji'
_publ_section_title
;
 Cp*RuCl-Catalyzed Formal Intermolecular Cyclotrimerization of Three
 Unsymmetrical Alkynes through a Boron Temporary Tether: 
 Regioselective Four-Component Coupling Synthesis of Phthalides
;
_journal_issue                   26
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9625
_journal_page_last               9631
_journal_paper_doi               10.1021/ja051377d
_journal_volume                  127
_journal_year                    2005
_chemical_formula_sum            'C13 H19 B O3'
_chemical_formula_weight         234.09
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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_method           SHELXL-97
_cell_angle_alpha                99.162(2)
_cell_angle_beta                 94.549(2)
_cell_angle_gamma                96.552(2)
_cell_formula_units_Z            2
_cell_length_a                   5.2808(5)
_cell_length_b                   10.0623(10)
_cell_length_c                   12.4829(12)
_cell_measurement_temperature    173(2)
_cell_volume                     647.34(11)
_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 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'CCD area 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  0.0142
_diffrn_reflns_av_sigmaI/netI    0.0200
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5026
_diffrn_reflns_theta_full        29.17
_diffrn_reflns_theta_max         29.17
_diffrn_reflns_theta_min         1.66
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.824162
_exptl_absorpt_correction_type   'empirical (SADABS)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.8
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         3395
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0531
_refine_ls_shift/su_max          0.044
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1129P)²+0.0337P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1522
_refine_ls_wR_factor_ref         0.1609
_reflns_number_gt                2821
_reflns_number_total             3395
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja051377dsup1.cif
_cod_data_source_block           yi21
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4119103
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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
C1 C 0.77171(19) 0.54876(10) 0.26603(9) 0.0251(2) Uani 1 1 d .
C2 C 0.96798(19) 0.59718(10) 0.35024(8) 0.0245(2) Uani 1 1 d .
C3 C 0.99235(19) 0.73177(10) 0.40319(8) 0.0249(2) Uani 1 1 d .
C4 C 0.8313(2) 0.82262(11) 0.37331(9) 0.0270(2) Uani 1 1 d .
H4 H 0.8506 0.9139 0.4102 0.032 Uiso 1 1 calc R
C5 C 0.6409(2) 0.77574(11) 0.28767(9) 0.0267(2) Uani 1 1 d .
C6 C 0.6115(2) 0.63975(11) 0.23626(9) 0.0277(2) Uani 1 1 d .
H6 H 0.4777 0.6089 0.1792 0.033 Uiso 1 1 calc R
C7 C 0.7372(2) 0.40299(11) 0.20961(9) 0.0292(2) Uani 1 1 d .
H7A H 0.5589 0.3786 0.1753 0.035 Uiso 1 1 calc R
H7B H 0.7638 0.3440 0.2648 0.035 Uiso 1 1 calc R
C8 C 0.9196(2) 0.37521(12) 0.12284(10) 0.0360(3) Uani 1 1 d .
H8A H 0.8893 0.4323 0.0666 0.043 Uiso 1 1 calc R
H8B H 1.0977 0.4024 0.1568 0.043 Uiso 1 1 calc R
C9 C 0.8917(2) 0.22822(13) 0.06809(11) 0.0401(3) Uani 1 1 d .
H9A H 0.7164 0.2025 0.0307 0.048 Uiso 1 1 calc R
H9B H 0.9127 0.1706 0.1247 0.048 Uiso 1 1 calc R
C10 C 1.0835(3) 0.19965(18) -0.01410(13) 0.0562(4) Uani 1 1 d .
H10A H 1.0683 0.2585 -0.0691 0.084 Uiso 1 1 calc R
H10B H 1.0490 0.1044 -0.0497 0.084 Uiso 1 1 calc R
H10C H 1.2573 0.2175 0.0234 0.084 Uiso 1 1 calc R
C11 C 1.2092(2) 0.75930(11) 0.49245(9) 0.0282(2) Uani 1 1 d .
H11A H 1.3388 0.8329 0.4798 0.034 Uiso 1 1 calc R
H11B H 1.1455 0.7863 0.5642 0.034 Uiso 1 1 calc R
C12 C 0.4642(2) 0.86797(12) 0.24676(10) 0.0330(3) Uani 1 1 d .
H12A H 0.5181 0.8927 0.1776 0.040 Uiso 1 1 calc R
H12B H 0.2876 0.8197 0.2320 0.040 Uiso 1 1 calc R
C13 C 0.3077(3) 1.07600(14) 0.28563(15) 0.0531(4) Uani 1 1 d .
H13A H 0.3675 1.1028 0.2189 0.080 Uiso 1 1 calc R
H13B H 0.3137 1.1569 0.3415 0.080 Uiso 1 1 calc R
H13C H 0.1313 1.0306 0.2701 0.080 Uiso 1 1 calc R
B1 B 1.1872(2) 0.53414(12) 0.40672(10) 0.0255(3) Uani 1 1 d .
O1 O 1.25061(15) 0.40753(8) 0.38604(7) 0.0302(2) Uani 1 1 d .
H1 H 1.3773 0.4008 0.4291 0.045 Uiso 1 1 calc R
O2 O 1.31835(15) 0.63330(8) 0.48889(6) 0.0290(2) Uani 1 1 d .
O3 O 0.4675(2) 0.98608(9) 0.32366(9) 0.0508(3) 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 0.0225(5) 0.0231(5) 0.0288(5) 0.0016(4) 0.0032(4) 0.0022(4)
C2 0.0224(5) 0.0232(5) 0.0277(5) 0.0028(4) 0.0028(4) 0.0035(4)
C3 0.0228(5) 0.0233(5) 0.0283(5) 0.0029(4) 0.0015(4) 0.0039(4)
C4 0.0257(5) 0.0230(5) 0.0313(5) 0.0024(4) 0.0002(4) 0.0047(4)
C5 0.0247(5) 0.0262(5) 0.0294(5) 0.0044(4) 0.0011(4) 0.0056(4)
C6 0.0239(5) 0.0279(5) 0.0297(5) 0.0020(4) -0.0017(4) 0.0039(4)
C7 0.0256(5) 0.0240(5) 0.0348(6) -0.0019(4) 0.0009(4) 0.0009(4)
C8 0.0362(6) 0.0304(6) 0.0382(6) -0.0035(5) 0.0079(5) 0.0006(4)
C9 0.0392(6) 0.0348(6) 0.0421(7) -0.0075(5) 0.0031(5) 0.0074(5)
C10 0.0452(8) 0.0633(10) 0.0509(8) -0.0209(7) 0.0071(6) 0.0099(7)
C11 0.0277(5) 0.0236(5) 0.0317(5) 0.0003(4) -0.0028(4) 0.0067(4)
C12 0.0338(6) 0.0301(6) 0.0353(6) 0.0044(4) -0.0030(4) 0.0109(4)
C13 0.0480(8) 0.0294(6) 0.0800(11) 0.0069(6) -0.0139(7) 0.0151(6)
B1 0.0237(5) 0.0237(5) 0.0291(6) 0.0041(4) 0.0031(4) 0.0040(4)
O1 0.0289(4) 0.0247(4) 0.0361(5) 0.0024(3) -0.0022(3) 0.0074(3)
O2 0.0278(4) 0.0245(4) 0.0334(4) 0.0013(3) -0.0039(3) 0.0079(3)
O3 0.0565(6) 0.0290(5) 0.0604(7) -0.0069(4) -0.0240(5) 0.0189(4)
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'
O O 0.0106 0.0060 '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
C6 C1 C2 117.74(9)
C6 C1 C7 121.29(10)
C2 C1 C7 120.97(9)
C3 C2 C1 119.97(9)
C3 C2 B1 105.12(9)
C1 C2 B1 134.90(10)
C4 C3 C2 122.13(10)
C4 C3 C11 127.29(9)
C2 C3 C11 110.58(9)
C3 C4 C5 117.96(10)
C4 C5 C6 120.04(10)
C4 C5 C12 121.75(10)
C6 C5 C12 118.20(10)
C1 C6 C5 122.11(10)
C1 C7 C8 113.33(9)
C9 C8 C7 113.70(10)
C8 C9 C10 113.47(12)
O2 C11 C3 105.66(8)
O3 C12 C5 110.75(9)
O1 B1 O2 122.56(10)
O1 B1 C2 129.41(10)
O2 B1 C2 108.03(9)
B1 O2 C11 110.59(8)
C12 O3 C13 111.70(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.3882(14)
C1 C2 1.4019(14)
C1 C7 1.5068(14)
C2 C3 1.3961(14)
C2 B1 1.5557(15)
C3 C4 1.3907(14)
C3 C11 1.5023(15)
C4 C5 1.3917(15)
C5 C6 1.4016(15)
C5 C12 1.5054(14)
C7 C8 1.5195(16)
C8 C9 1.5129(16)
C9 C10 1.5162(19)
C11 O2 1.4471(12)
C12 O3 1.4012(15)
C13 O3 1.4156(15)
B1 O1 1.3447(14)
B1 O2 1.3896(15)
