#------------------------------------------------------------------------------
#$Date: 2016-03-25 14:05:58 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179879 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/75/7017578.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_7017578
loop_
_publ_author_name
'Caputo, Christopher B.'
'Geier, Stephen J.'
'Ouyang, Eva Y.'
'Kreitner, Christoph'
'Stephan, Douglas W.'
_publ_section_title
;
 Chloro- and phenoxy-phosphines in frustrated Lewis pair additions to
 alkynes.
;
_journal_issue                   1
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              237
_journal_page_last               242
_journal_paper_doi               10.1039/c1dt11196e
_journal_volume                  41
_journal_year                    2012
_chemical_formula_sum            'C30 H15 B Cl2 F15 P'
_chemical_formula_weight         773.10
_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-97
_cell_angle_alpha                90.00
_cell_angle_beta                 118.0770(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.4163(4)
_cell_length_b                   18.3323(5)
_cell_length_c                   14.0090(5)
_cell_measurement_reflns_used    6416
_cell_measurement_temperature    493(2)
_cell_measurement_theta_max      25.28
_cell_measurement_theta_min      2.77
_cell_volume                     3040.05(17)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      493(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0342
_diffrn_reflns_av_sigmaI/netI    0.0476
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            25415
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    0.382
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6317
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     442
_refine_ls_number_reflns         6934
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0394
_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)+(0.0333P)²+1.4073P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0772
_refine_ls_wR_factor_ref         0.0915
_reflns_number_gt                4546
_reflns_number_total             6934
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1dt11196e.txt
_cod_data_source_block           cbc006_0m
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        3040.05(16)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7017578
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 0.33903(6) 0.42713(3) 0.94493(5) 0.05028(18) Uani 1 1 d .
Cl2 Cl 0.07910(5) 0.41733(3) 0.78614(5) 0.04431(17) Uani 1 1 d .
P1 P 0.20915(5) 0.48571(3) 0.84216(5) 0.02678(13) Uani 1 1 d .
F1 F 0.45700(10) 0.52510(7) 1.20987(11) 0.0412(3) Uani 1 1 d .
F2 F 0.50712(11) 0.43597(7) 1.37440(11) 0.0481(4) Uani 1 1 d .
F3 F 0.38303(12) 0.43713(8) 1.48317(12) 0.0539(4) Uani 1 1 d .
F4 F 0.21460(12) 0.53681(8) 1.42714(12) 0.0550(4) Uani 1 1 d .
F5 F 0.16313(11) 0.62713(7) 1.26489(11) 0.0414(3) Uani 1 1 d .
F6 F 0.42375(12) 0.64802(7) 1.00756(12) 0.0496(4) Uani 1 1 d .
F7 F 0.59755(12) 0.73933(8) 1.07581(14) 0.0595(4) Uani 1 1 d .
F8 F 0.65169(11) 0.82633(7) 1.25008(13) 0.0516(4) Uani 1 1 d .
F9 F 0.52575(12) 0.82066(8) 1.35541(12) 0.0552(4) Uani 1 1 d .
F10 F 0.34789(12) 0.73107(7) 1.28675(11) 0.0473(4) Uani 1 1 d .
F11 F 0.21166(11) 0.79023(7) 1.04995(12) 0.0467(4) Uani 1 1 d .
F12 F 0.00633(12) 0.84602(7) 0.95501(12) 0.0565(4) Uani 1 1 d .
F13 F -0.17659(11) 0.76337(8) 0.91389(13) 0.0580(4) Uani 1 1 d .
F14 F -0.14892(10) 0.61837(8) 0.96493(12) 0.0488(4) Uani 1 1 d .
F15 F 0.05714(10) 0.56019(6) 1.06082(11) 0.0364(3) Uani 1 1 d .
B1 B 0.26827(19) 0.62832(12) 1.1098(2) 0.0254(5) Uani 1 1 d .
C1 C 0.30025(16) 0.57785(10) 1.22010(17) 0.0255(5) Uani 1 1 d .
C2 C 0.38960(17) 0.52873(11) 1.25814(18) 0.0298(5) Uani 1 1 d .
C3 C 0.41894(18) 0.48187(11) 1.34417(18) 0.0339(5) Uani 1 1 d .
C4 C 0.35868(19) 0.48334(12) 1.40016(18) 0.0362(5) Uani 1 1 d .
C5 C 0.27277(19) 0.53320(12) 1.37102(19) 0.0353(5) Uani 1 1 d .
C6 C 0.24688(17) 0.57884(11) 1.28409(18) 0.0304(5) Uani 1 1 d .
C7 C 0.37682(17) 0.68392(11) 1.14459(17) 0.0269(5) Uani 1 1 d .
C8 C 0.44481(18) 0.68956(11) 1.09534(19) 0.0324(5) Uani 1 1 d .
C9 C 0.53587(18) 0.73627(12) 1.1290(2) 0.0371(6) Uani 1 1 d .
C10 C 0.56363(18) 0.78014(11) 1.2168(2) 0.0360(6) Uani 1 1 d .
C11 C 0.49996(19) 0.77702(11) 1.26984(19) 0.0355(6) Uani 1 1 d .
C12 C 0.40964(18) 0.72981(11) 1.23314(19) 0.0330(5) Uani 1 1 d .
C13 C 0.14718(17) 0.67169(11) 1.06505(16) 0.0258(5) Uani 1 1 d .
C14 C 0.12637(18) 0.74458(11) 1.03502(17) 0.0298(5) Uani 1 1 d .
C15 C 0.0202(2) 0.77529(11) 0.98512(19) 0.0357(5) Uani 1 1 d .
C16 C -0.07276(19) 0.73375(13) 0.96261(19) 0.0370(6) Uani 1 1 d .
C17 C -0.05853(18) 0.66112(12) 0.99026(18) 0.0331(5) Uani 1 1 d .
C18 C 0.04921(18) 0.63293(11) 1.03957(18) 0.0281(5) Uani 1 1 d .
C19 C 0.25898(17) 0.56956(10) 1.01742(17) 0.0249(4) Uani 1 1 d .
H19A H 0.3163 0.5349 1.0439 0.030 Uiso 1 1 calc R
C20 C 0.18637(16) 0.56073(10) 0.91179(17) 0.0234(4) Uani 1 1 d .
C21 C 0.11540(18) 0.67814(11) 0.81178(18) 0.0306(5) Uani 1 1 d .
H21A H 0.1899 0.6940 0.8417 0.037 Uiso 1 1 calc R
C22 C 0.0287(2) 0.72293(12) 0.7410(2) 0.0393(6) Uani 1 1 d .
H22A H 0.0453 0.7686 0.7234 0.047 Uiso 1 1 calc R
C23 C -0.0818(2) 0.70015(13) 0.6968(2) 0.0420(6) Uani 1 1 d .
H23A H -0.1396 0.7303 0.6492 0.050 Uiso 1 1 calc R
C24 C -0.10657(19) 0.63274(13) 0.7231(2) 0.0399(6) Uani 1 1 d .
H24A H -0.1814 0.6176 0.6938 0.048 Uiso 1 1 calc R
C25 C -0.02084(18) 0.58718(12) 0.79305(18) 0.0325(5) Uani 1 1 d .
H25A H -0.0384 0.5415 0.8099 0.039 Uiso 1 1 calc R
C26 C 0.09122(17) 0.60940(10) 0.83818(17) 0.0245(4) Uani 1 1 d .
C27 C 0.23315(19) 0.50773(12) 0.72715(19) 0.0346(5) Uani 1 1 d .
C28 C 0.2701(2) 0.43822(13) 0.6905(2) 0.0457(6) Uani 1 1 d .
H28A H 0.2829 0.4495 0.6302 0.069 Uiso 1 1 calc R
H28B H 0.2119 0.4019 0.6693 0.069 Uiso 1 1 calc R
H28C H 0.3386 0.4199 0.7491 0.069 Uiso 1 1 calc R
C29 C 0.1234(2) 0.53625(15) 0.6332(2) 0.0494(7) Uani 1 1 d .
H29A H 0.1360 0.5477 0.5729 0.074 Uiso 1 1 calc R
H29B H 0.0995 0.5794 0.6557 0.074 Uiso 1 1 calc R
H29C H 0.0658 0.4996 0.6123 0.074 Uiso 1 1 calc R
C30 C 0.3266(2) 0.56582(13) 0.7671(2) 0.0491(7) Uani 1 1 d .
H30A H 0.3423 0.5790 0.7092 0.074 Uiso 1 1 calc R
H30B H 0.3937 0.5466 0.8264 0.074 Uiso 1 1 calc R
H30C H 0.3020 0.6082 0.7906 0.074 Uiso 1 1 calc R
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'
F F 0.0171 0.0103 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C20 P1 C27 117.08(10)
C20 P1 Cl1 109.77(7)
C27 P1 Cl1 107.53(8)
C20 P1 Cl2 110.86(7)
C27 P1 Cl2 106.09(8)
Cl1 P1 Cl2 104.75(4)
C19 B1 C13 108.78(17)
C19 B1 C7 111.52(16)
C13 B1 C7 112.92(16)
C19 B1 C1 104.85(16)
C13 B1 C1 113.36(17)
C7 B1 C1 105.13(16)
C6 C1 C2 112.05(19)
C6 C1 B1 127.15(18)
C2 C1 B1 120.80(18)
F1 C2 C3 114.88(18)
F1 C2 C1 119.72(19)
C3 C2 C1 125.4(2)
F2 C3 C4 120.1(2)
F2 C3 C2 120.8(2)
C4 C3 C2 119.2(2)
F3 C4 C3 120.9(2)
F3 C4 C5 120.2(2)
C3 C4 C5 118.9(2)
F4 C5 C4 119.7(2)
F4 C5 C6 120.8(2)
C4 C5 C6 119.5(2)
F5 C6 C5 114.34(19)
F5 C6 C1 120.86(19)
C5 C6 C1 124.8(2)
C8 C7 C12 113.23(19)
C8 C7 B1 126.56(19)
C12 C7 B1 120.18(19)
F6 C8 C9 115.5(2)
F6 C8 C7 120.33(19)
C9 C8 C7 124.1(2)
F7 C9 C10 119.6(2)
F7 C9 C8 120.7(2)
C10 C9 C8 119.7(2)
F8 C10 C9 120.4(2)
F8 C10 C11 120.5(2)
C9 C10 C11 119.2(2)
F9 C11 C10 119.6(2)
F9 C11 C12 121.3(2)
C10 C11 C12 119.1(2)
F10 C12 C11 116.3(2)
F10 C12 C7 119.09(19)
C11 C12 C7 124.6(2)
C18 C13 C14 112.61(19)
C18 C13 B1 119.83(17)
C14 C13 B1 127.01(19)
F11 C14 C15 115.04(18)
F11 C14 C13 120.91(19)
C15 C14 C13 124.0(2)
F12 C15 C16 119.2(2)
F12 C15 C14 120.6(2)
C16 C15 C14 120.2(2)
F13 C16 C15 120.5(2)
F13 C16 C17 120.5(2)
C15 C16 C17 119.0(2)
F14 C17 C16 120.1(2)
F14 C17 C18 121.2(2)
C16 C17 C18 118.6(2)
F15 C18 C17 115.71(18)
F15 C18 C13 118.68(18)
C17 C18 C13 125.6(2)
C20 C19 B1 133.85(18)
C19 C20 C26 128.79(18)
C19 C20 P1 118.04(15)
C26 C20 P1 112.95(14)
C22 C21 C26 120.2(2)
C23 C22 C21 120.4(2)
C22 C23 C24 119.9(2)
C23 C24 C25 120.4(2)
C24 C25 C26 120.4(2)
C25 C26 C21 118.77(19)
C25 C26 C20 121.80(18)
C21 C26 C20 119.41(18)
C29 C27 C30 111.5(2)
C29 C27 C28 109.0(2)
C30 C27 C28 111.07(18)
C29 C27 P1 109.55(16)
C30 C27 P1 106.48(16)
C28 C27 P1 109.19(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 P1 1.9750(8)
Cl2 P1 1.9856(8)
P1 C20 1.794(2)
P1 C27 1.831(2)
F1 C2 1.362(2)
F2 C3 1.347(2)
F3 C4 1.349(3)
F4 C5 1.345(3)
F5 C6 1.354(2)
F6 C8 1.358(2)
F7 C9 1.351(3)
F8 C10 1.346(2)
F9 C11 1.344(2)
F10 C12 1.355(2)
F11 C14 1.352(2)
F12 C15 1.349(2)
F13 C16 1.344(2)
F14 C17 1.344(2)
F15 C18 1.359(2)
B1 C19 1.642(3)
B1 C13 1.645(3)
B1 C7 1.652(3)
B1 C1 1.675(3)
C1 C6 1.386(3)
C1 C2 1.390(3)
C2 C3 1.378(3)
C3 C4 1.366(3)
C4 C5 1.374(3)
C5 C6 1.380(3)
C7 C8 1.383(3)
C7 C12 1.388(3)
C8 C9 1.380(3)
C9 C10 1.366(3)
C10 C11 1.372(3)
C11 C12 1.377(3)
C13 C18 1.385(3)
C13 C14 1.389(3)
C14 C15 1.377(3)
C15 C16 1.366(3)
C16 C17 1.375(3)
C17 C18 1.376(3)
C19 C20 1.345(3)
C20 C26 1.500(3)
C21 C22 1.388(3)
C21 C26 1.394(3)
C22 C23 1.374(3)
C23 C24 1.375(3)
C24 C25 1.385(3)
C25 C26 1.390(3)
C27 C29 1.533(3)
C27 C30 1.535(3)
C27 C28 1.541(3)
