#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/35/4023530.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_4023530
loop_
_publ_author_name
'Gerald Schwab'
'Daniel Stern'
'Dietmar Stalke'
_publ_contact_author             'Prof. Dr. Dietmar Stalke'
_publ_contact_author_email       dstalke@chemie.uni-goettingen.de
_publ_section_title
;
 Structural and Variable-Temperature NMR Studies of
 9-Diisopropylphosphanylanthracenes and
 9,10-Bis(diisopropylphosphanyl)anthracenes
 and Their Oxidation Products
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5242
_journal_page_last               5247
_journal_paper_doi               10.1021/jo800294e
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C20 H23 P'
_chemical_formula_weight         294.35
_chemical_name_common            iPr2P(C14H9)
_chemical_name_systematic        9-Diisopropylphosphanylanthracene
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 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                 102.9650(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   33.822(4)
_cell_length_b                   8.1720(9)
_cell_length_c                   12.1131(13)
_cell_measurement_reflns_used    2441
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.79
_cell_measurement_theta_min      3.02
_cell_volume                     3262.7(6)
_computing_cell_refinement       'SAINT V7.23A'
_computing_data_collection       'APEX2 v2.1-4'
_computing_data_reduction        'SAINT V7.23A'
_computing_molecular_graphics    'XP in SHELXTL ver. 6.12'
_computing_publication_material  'XP in SHELXTL ver. 6.12'
_computing_structure_refinement  'SHELXL in SHELXTL ver. 6.12'
_computing_structure_solution    'SHELXS in SHELXTL ver. 6.12'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker Smart Apex II with D8-Goniometer'
_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  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0362
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            11153
_diffrn_reflns_theta_full        27.15
_diffrn_reflns_theta_max         27.15
_diffrn_reflns_theta_min         3.02
_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS-2004/1
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.882
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3586
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0454
_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)+(0.0656P)²+2.0867P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1265
_reflns_number_gt                2875
_reflns_number_total             3586
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo800294e-File001.cif
_cod_data_source_block           1a
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4023530
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.11326(5) 0.1629(2) 0.47167(14) 0.0166(4) Uani 1 1 d . . .
C2 C 0.11194(5) 0.2606(2) 0.37369(14) 0.0162(3) Uani 1 1 d . . .
C3 C 0.14456(5) 0.2699(2) 0.31615(15) 0.0194(4) Uani 1 1 d . . .
H3A H 0.1688 0.2105 0.3455 0.023 Uiso 1 1 calc R . .
C4 C 0.14194(5) 0.3607(2) 0.22103(15) 0.0211(4) Uani 1 1 d . . .
H4A H 0.1640 0.3617 0.1845 0.025 Uiso 1 1 calc R . .
C5 C 0.10656(5) 0.4546(2) 0.17506(15) 0.0211(4) Uani 1 1 d . . .
H5A H 0.1051 0.5177 0.1084 0.025 Uiso 1 1 calc R . .
C6 C 0.07512(5) 0.4531(2) 0.22729(15) 0.0193(4) Uani 1 1 d . . .
H6A H 0.0517 0.5170 0.1972 0.023 Uiso 1 1 calc R . .
C7 C 0.07644(5) 0.3570(2) 0.32702(14) 0.0173(4) Uani 1 1 d . . .
C8 C 0.04370(5) 0.3541(2) 0.37906(14) 0.0191(4) Uani 1 1 d . . .
H8A H 0.0208 0.4211 0.3498 0.023 Uiso 1 1 calc R . .
C9 C 0.04362(5) 0.2559(2) 0.47243(14) 0.0176(4) Uani 1 1 d . . .
C10 C 0.00871(5) 0.2499(2) 0.52089(15) 0.0208(4) Uani 1 1 d . . .
H10A H -0.0141 0.3167 0.4903 0.025 Uiso 1 1 calc R . .
C11 C 0.00778(5) 0.1501(2) 0.61000(15) 0.0235(4) Uani 1 1 d . . .
H11A H -0.0156 0.1469 0.6411 0.028 Uiso 1 1 calc R . .
C12 C 0.04181(5) 0.0507(2) 0.65634(15) 0.0227(4) Uani 1 1 d . . .
H12A H 0.0408 -0.0203 0.7177 0.027 Uiso 1 1 calc R . .
C13 C 0.07590(5) 0.0552(2) 0.61456(14) 0.0199(4) Uani 1 1 d . . .
H13A H 0.0985 -0.0107 0.6488 0.024 Uiso 1 1 calc R . .
C14 C 0.07865(5) 0.1573(2) 0.51987(14) 0.0166(4) Uani 1 1 d . . .
C15 C 0.15796(5) -0.1129(2) 0.42178(15) 0.0219(4) Uani 1 1 d . . .
H15A H 0.1567 -0.0489 0.3507 0.026 Uiso 1 1 calc R . .
C16 C 0.19674(6) -0.2156(2) 0.44707(17) 0.0294(4) Uani 1 1 d . . .
H16A H 0.1950 -0.3006 0.3891 0.044 Uiso 1 1 calc R . .
H16B H 0.2000 -0.2670 0.5217 0.044 Uiso 1 1 calc R . .
H16C H 0.2201 -0.1450 0.4467 0.044 Uiso 1 1 calc R . .
C17 C 0.12054(6) -0.2230(2) 0.40613(17) 0.0286(4) Uani 1 1 d . . .
H17A H 0.1204 -0.2996 0.3438 0.043 Uiso 1 1 calc R . .
H17B H 0.0960 -0.1554 0.3885 0.043 Uiso 1 1 calc R . .
H17C H 0.1213 -0.2843 0.4761 0.043 Uiso 1 1 calc R . .
C18 C 0.20376(5) 0.1580(2) 0.55853(15) 0.0213(4) Uani 1 1 d . . .
H18A H 0.2136 0.1576 0.4867 0.026 Uiso 1 1 calc R . .
C19 C 0.23578(5) 0.0791(3) 0.65400(16) 0.0285(4) Uani 1 1 d . . .
H19A H 0.2615 0.1386 0.6631 0.043 Uiso 1 1 calc R . .
H19B H 0.2398 -0.0353 0.6347 0.043 Uiso 1 1 calc R . .
H19C H 0.2265 0.0835 0.7250 0.043 Uiso 1 1 calc R . .
C20 C 0.19620(6) 0.3346(2) 0.59138(16) 0.0267(4) Uani 1 1 d . . .
H20A H 0.2220 0.3937 0.6104 0.040 Uiso 1 1 calc R . .
H20B H 0.1838 0.3340 0.6571 0.040 Uiso 1 1 calc R . .
H20C H 0.1779 0.3888 0.5276 0.040 Uiso 1 1 calc R . .
P1 P 0.156586(13) 0.03126(6) 0.54012(4) 0.01730(14) Uani 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 C1 C2 119.09(14) . . ?
C14 C1 P1 115.98(12) . . ?
C2 C1 P1 124.87(12) . . ?
C1 C2 C3 123.50(15) . . ?
C1 C2 C7 120.11(15) . . ?
C3 C2 C7 116.40(15) . . ?
C4 C3 C2 122.10(16) . . ?
C3 C4 C5 121.03(16) . . ?
C6 C5 C4 119.42(16) . . ?
C5 C6 C7 121.30(16) . . ?
C8 C7 C6 120.92(15) . . ?
C8 C7 C2 119.34(15) . . ?
C6 C7 C2 119.74(15) . . ?
C9 C8 C7 121.79(15) . . ?
C8 C9 C10 120.42(15) . . ?
C8 C9 C14 119.76(15) . . ?
C10 C9 C14 119.81(15) . . ?
C11 C10 C9 120.92(16) . . ?
C10 C11 C12 119.81(16) . . ?
C13 C12 C11 121.21(17) . . ?
C12 C13 C14 121.64(16) . . ?
C1 C14 C13 123.58(15) . . ?
C1 C14 C9 119.81(15) . . ?
C13 C14 C9 116.59(15) . . ?
C16 C15 C17 110.57(15) . . ?
C16 C15 P1 111.16(12) . . ?
C17 C15 P1 107.71(12) . . ?
C20 C18 C19 109.28(15) . . ?
C20 C18 P1 111.36(12) . . ?
C19 C18 P1 107.14(13) . . ?
C1 P1 C15 100.14(8) . . ?
C1 P1 C18 107.37(8) . . ?
C15 P1 C18 105.88(8) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C14 1.421(2) . ?
C1 C2 1.423(2) . ?
C1 P1 1.8565(17) . ?
C2 C3 1.433(2) . ?
C2 C7 1.442(2) . ?
C3 C4 1.357(2) . ?
C4 C5 1.425(2) . ?
C5 C6 1.354(2) . ?
C6 C7 1.433(2) . ?
C7 C8 1.392(2) . ?
C8 C9 1.387(2) . ?
C9 C10 1.432(2) . ?
C9 C14 1.442(2) . ?
C10 C11 1.359(3) . ?
C11 C12 1.417(3) . ?
C12 C13 1.360(2) . ?
C13 C14 1.438(2) . ?
C15 C16 1.529(2) . ?
C15 C17 1.529(2) . ?
C15 P1 1.8644(18) . ?
C18 C20 1.533(3) . ?
C18 C19 1.538(2) . ?
C18 P1 1.8732(18) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 C1 C2 C3 -177.58(15) . . . . ?
P1 C1 C2 C3 -0.6(2) . . . . ?
C14 C1 C2 C7 2.3(2) . . . . ?
P1 C1 C2 C7 179.37(12) . . . . ?
C1 C2 C3 C4 178.15(16) . . . . ?
C7 C2 C3 C4 -1.8(2) . . . . ?
C2 C3 C4 C5 1.3(3) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C4 C5 C6 C7 -0.9(3) . . . . ?
C5 C6 C7 C8 -178.89(16) . . . . ?
C5 C6 C7 C2 0.4(2) . . . . ?
C1 C2 C7 C8 0.3(2) . . . . ?
C3 C2 C7 C8 -179.77(15) . . . . ?
C1 C2 C7 C6 -179.04(15) . . . . ?
C3 C2 C7 C6 0.9(2) . . . . ?
C6 C7 C8 C9 176.87(15) . . . . ?
C2 C7 C8 C9 -2.5(2) . . . . ?
C7 C8 C9 C10 -177.14(16) . . . . ?
C7 C8 C9 C14 1.9(2) . . . . ?
C8 C9 C10 C11 177.81(17) . . . . ?
C14 C9 C10 C11 -1.2(3) . . . . ?
C9 C10 C11 C12 0.3(3) . . . . ?
C10 C11 C12 C13 1.2(3) . . . . ?
C11 C12 C13 C14 -1.7(3) . . . . ?
C2 C1 C14 C13 176.18(16) . . . . ?
P1 C1 C14 C13 -1.1(2) . . . . ?
C2 C1 C14 C9 -2.9(2) . . . . ?
P1 C1 C14 C9 179.81(12) . . . . ?
C12 C13 C14 C1 -178.43(16) . . . . ?
C12 C13 C14 C9 0.7(2) . . . . ?
C8 C9 C14 C1 0.8(2) . . . . ?
C10 C9 C14 C1 179.88(15) . . . . ?
C8 C9 C14 C13 -178.30(15) . . . . ?
C10 C9 C14 C13 0.7(2) . . . . ?
C14 C1 P1 C15 115.65(13) . . . . ?
C2 C1 P1 C15 -61.45(16) . . . . ?
C14 C1 P1 C18 -134.03(13) . . . . ?
C2 C1 P1 C18 48.87(16) . . . . ?
C16 C15 P1 C1 168.47(13) . . . . ?
C17 C15 P1 C1 -70.26(13) . . . . ?
C16 C15 P1 C18 56.99(15) . . . . ?
C17 C15 P1 C18 178.26(12) . . . . ?
C20 C18 P1 C1 38.16(15) . . . . ?
C19 C18 P1 C1 157.60(12) . . . . ?
C20 C18 P1 C15 144.47(13) . . . . ?
C19 C18 P1 C15 -96.08(13) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658696
