#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/00/31/7003116.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_7003116
loop_
_publ_author_name
'Muller, Alfred'
'Otto, Stefanus'
'Roodt, Andreas'
_publ_section_title
;
 Rapid phosphorus(iii) ligand evaluation utilising potassium
 selenocyanate
;
_journal_issue                   5
_journal_name_full               'Dalton Transactions'
_journal_page_first              650
_journal_page_last               657
_journal_paper_doi               10.1039/b712782k
_journal_year                    2008
_chemical_formula_moiety         'C18 H27 P Se'
_chemical_formula_sum            'C18 H27 P Se'
_chemical_formula_weight         353.33
_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'
_audit_creation_date             2006-03-16T10:41:44-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 98.26(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.100(2)
_cell_length_b                   13.668(3)
_cell_length_c                   11.773(2)
_cell_measurement_reflns_used    847
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.63
_cell_measurement_theta_min      2.38
_cell_volume                     1767.6(6)
_computing_cell_refinement       'SAINT-Plus (Bruker, 1999)'
_computing_data_collection       'SMART-NT (Bruker, 1998)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 1999)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al, 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
;
Bruker SMART CCD 1K
;
_diffrn_measurement_method       ω
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12106
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         1.85
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.205
_exptl_absorpt_correction_T_max  0.7477
_exptl_absorpt_correction_T_min  0.5772
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS (Bruker, 2004)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cuboid
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.28
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         4364
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_gt           0.0375
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0322P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.082
_reflns_number_gt                2688
_reflns_number_total             4364
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b712782k.txt
_cod_data_source_block           sephcy2
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7003116
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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
_atom_site_disorder_assembly
Se Se 0.62132(3) 0.40178(2) 0.71374(2) 0.05356(11) Uani 1 d . . .
P P 0.66970(6) 0.33799(5) 0.56180(5) 0.03691(16) Uani 1 d . . .
C11 C 0.7048(2) 0.43245(16) 0.46078(18) 0.0371(6) Uani 1 d . . .
H11 H 0.6327 0.4743 0.4445 0.045 Uiso 1 calc R . .
C12 C 0.8095(2) 0.49754(18) 0.5134(2) 0.0470(6) Uani 1 d . . .
H12A H 0.7885 0.5276 0.5826 0.056 Uiso 1 calc R . .
H12B H 0.8813 0.4575 0.5349 0.056 Uiso 1 calc R . .
C13 C 0.8390(3) 0.57731(19) 0.4318(2) 0.0532(7) Uani 1 d . . .
H13A H 0.7716 0.623 0.4188 0.064 Uiso 1 calc R . .
H13B H 0.9105 0.6129 0.4666 0.064 Uiso 1 calc R . .
C14 C 0.8624(2) 0.5352(2) 0.3177(2) 0.0537(7) Uani 1 d . . .
H14A H 0.9355 0.4954 0.3294 0.064 Uiso 1 calc R . .
H14B H 0.8753 0.5881 0.2659 0.064 Uiso 1 calc R . .
C15 C 0.7556(2) 0.47305(19) 0.2642(2) 0.0502(7) Uani 1 d . . .
H15A H 0.7736 0.4452 0.1927 0.06 Uiso 1 calc R . .
H15B H 0.6838 0.5138 0.247 0.06 Uiso 1 calc R . .
C16 C 0.7305(2) 0.39101(17) 0.34539(19) 0.0450(6) Uani 1 d . . .
H16A H 0.8004 0.3477 0.3583 0.054 Uiso 1 calc R . .
H16B H 0.661 0.3531 0.3106 0.054 Uiso 1 calc R . .
C21 C 0.5494(2) 0.25985(17) 0.48658(19) 0.0386(6) Uani 1 d . . .
H21 H 0.5813 0.2293 0.4217 0.046 Uiso 1 calc R . .
C22 C 0.4376(2) 0.31981(18) 0.4386(2) 0.0507(7) Uani 1 d . . .
H22A H 0.409 0.3558 0.5005 0.061 Uiso 1 calc R . .
H22B H 0.46 0.3668 0.3835 0.061 Uiso 1 calc R . .
C23 C 0.3356(2) 0.2549(2) 0.3804(2) 0.0635(8) Uani 1 d . . .
H23A H 0.2644 0.2947 0.3555 0.076 Uiso 1 calc R . .
H23B H 0.3609 0.2249 0.313 0.076 Uiso 1 calc R . .
C24 C 0.3027(2) 0.1755(2) 0.4608(3) 0.0651(8) Uani 1 d . . .
H24A H 0.2703 0.2053 0.5247 0.078 Uiso 1 calc R . .
H24B H 0.2401 0.1337 0.4202 0.078 Uiso 1 calc R . .
C25 C 0.4122(3) 0.11466(19) 0.5054(3) 0.0581(7) Uani 1 d . . .
H25A H 0.4397 0.0798 0.4421 0.07 Uiso 1 calc R . .
H25B H 0.3897 0.0666 0.5592 0.07 Uiso 1 calc R . .
C26 C 0.5160(2) 0.17794(18) 0.5649(2) 0.0516(7) Uani 1 d . . .
H26A H 0.5868 0.1372 0.5878 0.062 Uiso 1 calc R . .
H26B H 0.4919 0.2064 0.6337 0.062 Uiso 1 calc R . .
C31 C 0.8054(2) 0.26086(17) 0.5881(2) 0.0404(6) Uani 1 d . . .
C32 C 0.8315(2) 0.19207(19) 0.5083(2) 0.0505(7) Uani 1 d . . .
H32 H 0.7779 0.183 0.4408 0.061 Uiso 1 calc R . .
C33 C 0.9369(3) 0.1370(2) 0.5287(3) 0.0663(8) Uani 1 d . . .
H33 H 0.9536 0.0907 0.4752 0.08 Uiso 1 calc R . .
C34 C 1.0178(3) 0.1504(2) 0.6286(3) 0.0722(9) Uani 1 d . . .
H34 H 1.0892 0.114 0.6418 0.087 Uiso 1 calc R . .
C35 C 0.9920(2) 0.2174(2) 0.7074(3) 0.0627(8) Uani 1 d . . .
H35 H 1.0454 0.2255 0.7752 0.075 Uiso 1 calc R . .
C36 C 0.8876(2) 0.27354(19) 0.6879(2) 0.0491(7) Uani 1 d . . .
H36 H 0.8723 0.32 0.7417 0.059 Uiso 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 0 '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'
Se Se -0.0929 2.2259 '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
C31 P C11 105.61(11) . . ?
C31 P C21 105.71(11) . . ?
C11 P C21 107.72(10) . . ?
C31 P Se 113.28(8) . . ?
C11 P Se 111.07(8) . . ?
C21 P Se 112.97(8) . . ?
C12 C11 C16 110.3(2) . . ?
C12 C11 P 111.62(16) . . ?
C16 C11 P 113.43(16) . . ?
C12 C11 H11 107.0 . . ?
C16 C11 H11 107.0 . . ?
P C11 H11 107.0 . . ?
C13 C12 C11 112.5(2) . . ?
C13 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C14 C13 C12 111.5(2) . . ?
C14 C13 H13A 109.3 . . ?
C12 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 C15 110.9(2) . . ?
C13 C14 H14A 109.5 . . ?
C15 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 108.0 . . ?
C14 C15 C16 110.6(2) . . ?
C14 C15 H15A 109.5 . . ?
C16 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C15 C16 C11 110.94(19) . . ?
C15 C16 H16A 109.5 . . ?
C11 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 108.0 . . ?
C22 C21 C26 111.2(2) . . ?
C22 C21 P 111.26(16) . . ?
C26 C21 P 110.97(16) . . ?
C22 C21 H21 107.7 . . ?
C26 C21 H21 107.7 . . ?
P C21 H21 107.7 . . ?
C23 C22 C21 111.5(2) . . ?
C23 C22 H22A 109.3 . . ?
C21 C22 H22A 109.3 . . ?
C23 C22 H22B 109.3 . . ?
C21 C22 H22B 109.3 . . ?
H22A C22 H22B 108.0 . . ?
C24 C23 C22 111.5(2) . . ?
C24 C23 H23A 109.3 . . ?
C22 C23 H23A 109.3 . . ?
C24 C23 H23B 109.3 . . ?
C22 C23 H23B 109.3 . . ?
H23A C23 H23B 108.0 . . ?
C25 C24 C23 111.0(2) . . ?
C25 C24 H24A 109.4 . . ?
C23 C24 H24A 109.4 . . ?
C25 C24 H24B 109.4 . . ?
C23 C24 H24B 109.4 . . ?
H24A C24 H24B 108.0 . . ?
C24 C25 C26 111.4(2) . . ?
C24 C25 H25A 109.3 . . ?
C26 C25 H25A 109.3 . . ?
C24 C25 H25B 109.3 . . ?
C26 C25 H25B 109.3 . . ?
H25A C25 H25B 108.0 . . ?
C25 C26 C21 111.7(2) . . ?
C25 C26 H26A 109.3 . . ?
C21 C26 H26A 109.3 . . ?
C25 C26 H26B 109.3 . . ?
C21 C26 H26B 109.3 . . ?
H26A C26 H26B 107.9 . . ?
C32 C31 C36 118.7(2) . . ?
C32 C31 P 121.49(19) . . ?
C36 C31 P 119.75(19) . . ?
C33 C32 C31 120.3(3) . . ?
C33 C32 H32 119.9 . . ?
C31 C32 H32 119.9 . . ?
C32 C33 C34 120.3(3) . . ?
C32 C33 H33 119.9 . . ?
C34 C33 H33 119.9 . . ?
C35 C34 C33 119.6(3) . . ?
C35 C34 H34 120.2 . . ?
C33 C34 H34 120.2 . . ?
C34 C35 C36 120.9(3) . . ?
C34 C35 H35 119.6 . . ?
C36 C35 H35 119.6 . . ?
C35 C36 C31 120.3(3) . . ?
C35 C36 H36 119.9 . . ?
C31 C36 H36 119.9 . . ?
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
Se P 2.1271(8) . ?
P C31 1.828(2) . ?
P C11 1.835(2) . ?
P C21 1.835(2) . ?
C11 C12 1.523(3) . ?
C11 C16 1.536(3) . ?
C11 H11 0.9800 . ?
C12 C13 1.520(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.518(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.519(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.525(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C21 C22 1.526(3) . ?
C21 C26 1.530(3) . ?
C21 H21 0.9800 . ?
C22 C23 1.521(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.519(4) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.504(4) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.527(4) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C31 C32 1.390(3) . ?
C31 C36 1.391(3) . ?
C32 C33 1.384(4) . ?
C32 H32 0.9300 . ?
C33 C34 1.385(4) . ?
C33 H33 0.9300 . ?
C34 C35 1.362(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.381(4) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
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
C31 P C11 C12 -63.94(19) . . . . ?
C21 P C11 C12 -176.56(16) . . . . ?
Se P C11 C12 59.24(18) . . . . ?
C31 P C11 C16 61.4(2) . . . . ?
C21 P C11 C16 -51.2(2) . . . . ?
Se P C11 C16 -175.41(15) . . . . ?
C16 C11 C12 C13 53.8(3) . . . . ?
P C11 C12 C13 -179.16(17) . . . . ?
C11 C12 C13 C14 -54.0(3) . . . . ?
C12 C13 C14 C15 55.2(3) . . . . ?
C13 C14 C15 C16 -57.3(3) . . . . ?
C14 C15 C16 C11 57.8(3) . . . . ?
C12 C11 C16 C15 -55.5(3) . . . . ?
P C11 C16 C15 178.44(17) . . . . ?
C31 P C21 C22 -168.95(17) . . . . ?
C11 P C21 C22 -56.41(19) . . . . ?
Se P C21 C22 66.64(18) . . . . ?
C31 P C21 C26 66.69(19) . . . . ?
C11 P C21 C26 179.23(17) . . . . ?
Se P C21 C26 -57.73(18) . . . . ?
C26 C21 C22 C23 -53.4(3) . . . . ?
P C21 C22 C23 -177.65(19) . . . . ?
C21 C22 C23 C24 55.2(3) . . . . ?
C22 C23 C24 C25 -56.6(3) . . . . ?
C23 C24 C25 C26 56.3(3) . . . . ?
C24 C25 C26 C21 -55.0(3) . . . . ?
C22 C21 C26 C25 53.2(3) . . . . ?
P C21 C26 C25 177.62(18) . . . . ?
C11 P C31 C32 -76.8(2) . . . . ?
C21 P C31 C32 37.2(2) . . . . ?
Se P C31 C32 161.43(18) . . . . ?
C11 P C31 C36 100.4(2) . . . . ?
C21 P C31 C36 -145.58(19) . . . . ?
Se P C31 C36 -21.4(2) . . . . ?
C36 C31 C32 C33 0.6(4) . . . . ?
P C31 C32 C33 177.8(2) . . . . ?
C31 C32 C33 C34 -0.5(4) . . . . ?
C32 C33 C34 C35 0.9(5) . . . . ?
C33 C34 C35 C36 -1.4(4) . . . . ?
C34 C35 C36 C31 1.5(4) . . . . ?
C32 C31 C36 C35 -1.1(4) . . . . ?
P C31 C36 C35 -178.4(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 25934691
