#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/48/1504870.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_1504870
loop_
_publ_author_name
'Anderson, Brian J.'
'Guino-o, Marites A'
'Glueck, David S.'
'Golen, James A.'
'DiPasquale, Antonio G.'
'Liable-Sands, Louise M'
'Rheingold, Arnold L.'
_publ_section_title
;
 Platinum-catalyzed enantioselective tandem alkylation/arylation of
 primary phosphines. Asymmetric synthesis of P-stereogenic
 1-phosphaacenaphthenes.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              4425
_journal_page_last               4428
_journal_paper_doi               10.1021/ol801616s
_journal_volume                  10
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_sum            'C17 H16 B P'
_chemical_formula_weight         262.08
_chemical_name_systematic
; 

 ? 

;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.9633(10)
_cell_length_b                   12.6914(12)
_cell_length_c                   23.225(2)
_cell_measurement_reflns_used    5727
_cell_measurement_temperature    208(2)
_cell_measurement_theta_max      27.23
_cell_measurement_theta_min      2.38
_cell_volume                     2936.8(5)
_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, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      208(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0464
_diffrn_reflns_av_sigmaI/netI    0.0597
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            14126
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  0.9866
_exptl_absorpt_correction_T_min  0.9462
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         5633
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0500P)²+0.0800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0974
_refine_ls_wR_factor_ref         0.1097
_reflns_number_gt                4358
_reflns_number_total             5633
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol801616s_si_002.cif
_cod_data_source_block           glu271
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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        2936.7(5)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1504870
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
P1 P 0.70010(7) 0.70475(6) 0.82209(3) 0.04255(18) Uani 1 1 d .
P1' P 0.58901(8) 0.26169(6) 0.94013(3) 0.0469(2) Uani 1 1 d .
B1 B 0.8223(4) 0.7635(3) 0.76742(14) 0.0523(9) Uani 1 1 d .
B1' B 0.5094(5) 0.1421(4) 0.9032(2) 0.0714(12) Uani 1 1 d .
C1 C 0.6277(3) 0.5762(2) 0.79954(14) 0.0563(8) Uani 1 1 d .
H1A H 0.6647 0.5544 0.7623 0.068 Uiso 1 1 calc R
H1B H 0.6480 0.5216 0.8281 0.068 Uiso 1 1 calc R
C1' C 0.6393(3) 0.2456(2) 1.01610(12) 0.0510(7) Uani 1 1 d .
H1'A H 0.6106 0.1767 1.0306 0.061 Uiso 1 1 calc R
H1'B H 0.7370 0.2509 1.0199 0.061 Uiso 1 1 calc R
C2 C 0.4784(3) 0.5928(2) 0.79501(11) 0.0444(7) Uani 1 1 d .
C2' C 0.5716(3) 0.3328(2) 1.04941(11) 0.0455(7) Uani 1 1 d .
C3 C 0.3861(3) 0.5219(2) 0.77637(12) 0.0519(8) Uani 1 1 d .
H3A H 0.4128 0.4544 0.7644 0.062 Uiso 1 1 calc R
C3' C 0.5830(3) 0.3543(3) 1.10680(13) 0.0597(8) Uani 1 1 d .
H3'A H 0.6413 0.3145 1.1300 0.072 Uiso 1 1 calc R
C4 C 0.2494(4) 0.5512(3) 0.77526(13) 0.0624(9) Uani 1 1 d .
H4A H 0.1861 0.5025 0.7614 0.075 Uiso 1 1 calc R
C4' C 0.5065(4) 0.4368(3) 1.13089(15) 0.0713(10) Uani 1 1 d .
H4'A H 0.5149 0.4508 1.1705 0.086 Uiso 1 1 calc R
C5 C 0.2052(3) 0.6481(3) 0.79371(13) 0.0600(8) Uani 1 1 d .
H5A H 0.1130 0.6640 0.7938 0.072 Uiso 1 1 calc R
C5' C 0.4208(4) 0.4969(3) 1.09890(14) 0.0647(9) Uani 1 1 d .
H5'A H 0.3707 0.5508 1.1165 0.078 Uiso 1 1 calc R
C6 C 0.2994(3) 0.7233(2) 0.81237(11) 0.0473(7) Uani 1 1 d .
C6' C 0.4076(3) 0.4780(2) 1.03908(13) 0.0513(7) Uani 1 1 d .
C7 C 0.2677(3) 0.8277(3) 0.83018(12) 0.0564(8) Uani 1 1 d .
H7A H 0.1775 0.8494 0.8314 0.068 Uiso 1 1 calc R
C7' C 0.3242(3) 0.5345(2) 1.00098(16) 0.0607(9) Uani 1 1 d .
H7'A H 0.2715 0.5900 1.0154 0.073 Uiso 1 1 calc R
C8 C 0.3660(3) 0.8964(2) 0.84550(12) 0.0517(8) Uani 1 1 d .
H8A H 0.3425 0.9652 0.8565 0.062 Uiso 1 1 calc R
C8' C 0.3181(3) 0.5110(2) 0.94410(16) 0.0602(9) Uani 1 1 d .
H8'A H 0.2620 0.5508 0.9199 0.072 Uiso 1 1 calc R
C9 C 0.5040(3) 0.8664(2) 0.84530(11) 0.0465(7) Uani 1 1 d .
H9A H 0.5709 0.9147 0.8562 0.056 Uiso 1 1 calc R
C9' C 0.3949(3) 0.4272(2) 0.92043(13) 0.0518(8) Uani 1 1 d .
H9'A H 0.3892 0.4109 0.8810 0.062 Uiso 1 1 calc R
C10 C 0.5374(3) 0.7663(2) 0.82902(10) 0.0400(6) Uani 1 1 d .
C10' C 0.4774(3) 0.3706(2) 0.95594(12) 0.0424(6) Uani 1 1 d .
C11 C 0.4372(3) 0.6950(2) 0.81268(10) 0.0378(6) Uani 1 1 d .
C11' C 0.4850(3) 0.3953(2) 1.01508(12) 0.0414(6) Uani 1 1 d .
C12 C 0.7678(3) 0.6891(2) 0.89399(11) 0.0408(6) Uani 1 1 d .
C12' C 0.7324(3) 0.3174(2) 0.90331(12) 0.0442(7) Uani 1 1 d .
C13 C 0.9030(3) 0.7136(2) 0.90382(12) 0.0490(7) Uani 1 1 d .
H13A H 0.9562 0.7399 0.8737 0.059 Uiso 1 1 calc R
C13' C 0.7617(3) 0.2887(3) 0.84734(13) 0.0576(8) Uani 1 1 d .
H13B H 0.7073 0.2397 0.8279 0.069 Uiso 1 1 calc R
C14 C 0.9579(3) 0.6990(3) 0.95756(14) 0.0643(9) Uani 1 1 d .
H14A H 1.0489 0.7149 0.9639 0.077 Uiso 1 1 calc R
C14' C 0.8725(3) 0.3329(3) 0.81986(15) 0.0693(10) Uani 1 1 d .
H14B H 0.8925 0.3136 0.7818 0.083 Uiso 1 1 calc R
C15 C 0.8802(4) 0.6611(3) 1.00230(14) 0.0725(11) Uani 1 1 d .
H15A H 0.9182 0.6517 1.0390 0.087 Uiso 1 1 calc R
C15' C 0.9520(3) 0.4037(3) 0.84750(16) 0.0663(9) Uani 1 1 d .
H15B H 1.0263 0.4330 0.8284 0.080 Uiso 1 1 calc R
C16 C 0.7469(4) 0.6373(3) 0.99305(13) 0.0671(10) Uani 1 1 d .
H16A H 0.6940 0.6118 1.0236 0.081 Uiso 1 1 calc R
C16' C 0.9243(3) 0.4328(2) 0.90358(15) 0.0571(8) Uani 1 1 d .
H16B H 0.9799 0.4813 0.9227 0.069 Uiso 1 1 calc R
C17 C 0.6903(3) 0.6506(2) 0.93904(12) 0.0525(7) Uani 1 1 d .
H17A H 0.5997 0.6336 0.9329 0.063 Uiso 1 1 calc R
C17' C 0.8145(3) 0.3902(2) 0.93130(13) 0.0493(7) Uani 1 1 d .
H17B H 0.7949 0.4104 0.9693 0.059 Uiso 1 1 calc R
H1H H 0.431(4) 0.111(3) 0.9314(14) 0.081(11) Uiso 1 1 d .
H1E H 0.763(3) 0.778(2) 0.7290(12) 0.059(8) Uiso 1 1 d .
H1D H 0.890(3) 0.700(3) 0.7594(13) 0.079(10) Uiso 1 1 d .
H1G H 0.473(3) 0.171(2) 0.8588(13) 0.062(9) Uiso 1 1 d .
H1C H 0.871(3) 0.840(2) 0.7869(12) 0.063(9) Uiso 1 1 d .
H1F H 0.584(4) 0.091(3) 0.9000(17) 0.113(15) Uiso 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 0.0033 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C10 P1 C12 107.43(12)
C10 P1 C1 93.24(13)
C12 P1 C1 107.92(14)
C10 P1 B1 117.51(15)
C12 P1 B1 114.71(15)
C1 P1 B1 113.75(17)
C12' P1' C10' 106.38(12)
C12' P1' C1' 106.32(13)
C10' P1' C1' 93.27(13)
C12' P1' B1' 115.18(18)
C10' P1' B1' 116.19(19)
C1' P1' B1' 116.9(2)
P1 B1 H1E 105.6(15)
P1 B1 H1D 102.7(17)
H1E B1 H1D 109(2)
P1 B1 H1C 109.2(14)
H1E B1 H1C 114(2)
H1D B1 H1C 115(2)
P1' B1' H1H 108.6(17)
P1' B1' H1G 106.0(15)
H1H B1' H1G 115(2)
P1' B1' H1F 104(2)
H1H B1' H1F 110(3)
H1G B1' H1F 112(3)
C2 C1 P1 106.3(2)
C2 C1 H1A 110.5
P1 C1 H1A 110.5
C2 C1 H1B 110.5
P1 C1 H1B 110.5
H1A C1 H1B 108.7
C2' C1' P1' 106.74(18)
C2' C1' H1'A 110.4
P1' C1' H1'A 110.4
C2' C1' H1'B 110.4
P1' C1' H1'B 110.4
H1'A C1' H1'B 108.6
C3 C2 C11 120.0(3)
C3 C2 C1 126.8(3)
C11 C2 C1 113.2(3)
C3' C2' C11' 119.2(3)
C3' C2' C1' 127.6(3)
C11' C2' C1' 113.2(2)
C2 C3 C4 119.1(3)
C2 C3 H3A 120.5
C4 C3 H3A 120.5
C2' C3' C4' 119.4(3)
C2' C3' H3'A 120.3
C4' C3' H3'A 120.3
C5 C4 C3 122.6(3)
C5 C4 H4A 118.7
C3 C4 H4A 118.7
C5' C4' C3' 122.5(3)
C5' C4' H4'A 118.8
C3' C4' H4'A 118.8
C4 C5 C6 119.3(3)
C4 C5 H5A 120.4
C6 C5 H5A 120.4
C4' C5' C6' 119.8(3)
C4' C5' H5'A 120.1
C6' C5' H5'A 120.1
C5 C6 C11 118.4(3)
C5 C6 C7 124.9(3)
C11 C6 C7 116.6(3)
C7' C6' C5' 125.7(3)
C7' C6' C11' 116.8(3)
C5' C6' C11' 117.5(3)
C8 C7 C6 120.9(3)
C8 C7 H7A 119.5
C6 C7 H7A 119.5
C8' C7' C6' 121.7(3)
C8' C7' H7'A 119.1
C6' C7' H7'A 119.1
C7 C8 C9 121.5(3)
C7 C8 H8A 119.2
C9 C8 H8A 119.2
C7' C8' C9' 121.1(3)
C7' C8' H8'A 119.4
C9' C8' H8'A 119.4
C10 C9 C8 118.9(3)
C10 C9 H9A 120.6
C8 C9 H9A 120.6
C10' C9' C8' 118.9(3)
C10' C9' H9'A 120.5
C8' C9' H9'A 120.6
C9 C10 C11 120.2(3)
C9 C10 P1 130.2(2)
C11 C10 P1 109.62(18)
C9' C10' C11' 120.2(3)
C9' C10' P1' 130.3(2)
C11' C10' P1' 109.5(2)
C10 C11 C6 121.8(2)
C10 C11 C2 117.5(2)
C6 C11 C2 120.6(3)
C10' C11' C2' 117.2(2)
C10' C11' C6' 121.2(3)
C2' C11' C6' 121.6(3)
C17 C12 C13 119.3(3)
C17 C12 P1 121.7(2)
C13 C12 P1 118.9(2)
C13' C12' C17' 119.3(3)
C13' C12' P1' 120.6(2)
C17' C12' P1' 120.1(2)
C14 C13 C12 120.0(3)
C14 C13 H13A 120.0
C12 C13 H13A 120.0
C12' C13' C14' 119.5(3)
C12' C13' H13B 120.3
C14' C13' H13B 120.3
C13 C14 C15 120.4(3)
C13 C14 H14A 119.8
C15 C14 H14A 119.8
C15' C14' C13' 120.8(3)
C15' C14' H14B 119.6
C13' C14' H14B 119.6
C16 C15 C14 119.9(3)
C16 C15 H15A 120.0
C14 C15 H15A 120.0
C14' C15' C16' 120.4(3)
C14' C15' H15B 119.8
C16' C15' H15B 119.8
C15 C16 C17 120.4(3)
C15 C16 H16A 119.8
C17 C16 H16A 119.8
C17' C16' C15' 119.6(3)
C17' C16' H16B 120.2
C15' C16' H16B 120.2
C12 C17 C16 119.9(3)
C12 C17 H17A 120.0
C16 C17 H17A 120.0
C16' C17' C12' 120.5(3)
C16' C17' H17B 119.8
C12' C17' H17B 119.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 C10 1.807(3)
P1 C12 1.812(3)
P1 C1 1.859(3)
P1 B1 1.911(3)
P1' C12' 1.809(3)
P1' C10' 1.812(3)
P1' C1' 1.845(3)
P1' B1' 1.915(4)
B1 H1E 1.08(3)
B1 H1D 1.07(3)
B1 H1C 1.17(3)
B1' H1H 1.10(3)
B1' H1G 1.15(3)
B1' H1F 0.99(4)
C1 C2 1.505(4)
C1 H1A 0.9800
C1 H1B 0.9800
C1' C2' 1.509(4)
C1' H1'A 0.9800
C1' H1'B 0.9800
C2 C3 1.357(4)
C2 C11 1.421(4)
C2' C3' 1.365(4)
C2' C11' 1.417(4)
C3 C4 1.412(5)
C3 H3A 0.9400
C3' C4' 1.410(5)
C3' H3'A 0.9400
C4 C5 1.375(5)
C4 H4A 0.9400
C4' C5' 1.366(5)
C4' H4'A 0.9400
C5 C6 1.406(4)
C5 H5A 0.9400
C5' C6' 1.416(4)
C5' H5'A 0.9400
C6 C11 1.420(4)
C6 C7 1.423(4)
C6' C7' 1.410(4)
C6' C11' 1.417(4)
C7 C8 1.359(4)
C7 H7A 0.9400
C7' C8' 1.356(5)
C7' H7'A 0.9400
C8 C9 1.427(4)
C8 H8A 0.9400
C8' C9' 1.421(4)
C8' H8'A 0.9400
C9 C10 1.367(4)
C9 H9A 0.9400
C9' C10' 1.367(4)
C9' H9'A 0.9400
C10 C11 1.401(3)
C10' C11' 1.411(4)
C12 C17 1.389(4)
C12 C13 1.401(4)
C12' C13' 1.381(4)
C12' C17' 1.395(4)
C13 C14 1.375(4)
C13 H13A 0.9400
C13' C14' 1.393(4)
C13' H13B 0.9400
C14 C15 1.382(5)
C14 H14A 0.9400
C14' C15' 1.359(5)
C14' H14B 0.9400
C15 C16 1.380(5)
C15 H15A 0.9400
C15' C16' 1.382(4)
C15' H15B 0.9400
C16 C17 1.385(4)
C16 H16A 0.9400
C16' C17' 1.380(4)
C16' H16B 0.9400
C17 H17A 0.9400
C17' H17B 0.9400
