#------------------------------------------------------------------------------
#$Date: 2016-02-21 11:56:54 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176809 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/02/2240225.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# 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_2240225
loop_
_publ_author_name
'Janzen, Daron E.'
'Kooyman, Arianna M.'
'Lange, Kayla A.'
_publ_section_title
;
 Crystal structures of bis[2-(diphenylphosphinothioyl)phenyl] ether and
 bis{2-[diphenyl(selanylidene)phosphanyl]phenyl} ether
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              536
_journal_page_last               540
_journal_paper_doi               10.1107/S1600536814023988
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C36 H28 O P2 Se2'
_chemical_formula_moiety         'C36 H28 O P2 Se2'
_chemical_formula_sum            'C36 H28 O P2 Se2'
_chemical_formula_weight         696.44
_chemical_name_common
;
bis{2-[Diphenyl(selanylidene)phosphanyl]phenyl} ether
;
_chemical_name_systematic
(2-{2-[Diphenyl(selanylidene)phosphanyl]phenoxy}phenyl)diphenyl-λ⁵-phosphaneselone
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 109.226(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0964(15)
_cell_length_b                   13.0854(13)
_cell_length_c                   17.5918(18)
_cell_measurement_reflns_used    13788
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.59
_cell_measurement_theta_min      3.06
_cell_volume                     3064.0(6)
_computing_cell_refinement
;
CrystalClear-SM Expert (Rigaku Americas and Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert (Rigaku Americas and Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert (Rigaku Americas and Rigaku, 2011)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
CrystalStructure (Rigaku, 2010)
;
_computing_structure_refinement
;
SHELXL2013 (Sheldrick, 2008)
;
_computing_structure_solution
;
SIR2004 (Burla et al., 2005)
;
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 6.849
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            15840
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         3.061
_exptl_absorpt_coefficient_mu    2.546
_exptl_absorpt_correction_T_max  0.737
_exptl_absorpt_correction_T_min  0.556
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(REQAB; Rigaku, 1998)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1400
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.408
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         3521
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0321
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0183P)²+4.7666P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0624
_refine_ls_wR_factor_ref         0.0659
_reflns_number_gt                2958
_reflns_number_total             3521
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su5010sup1.cif
_cod_data_source_block           2
_cod_database_code               2240225
_cod_database_fobs_code          2240225
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2.013
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
Se Se1 0.15497(2) 0.31054(2) 0.63637(2) 0.02846(8) Uani d 1
P P1 -0.00071(4) 0.28040(4) 0.58870(3) 0.01801(12) Uani d 1
O O1 0.0000 0.35271(16) 0.7500 0.0191(4) Uani d 1
C C1 -0.03973(16) 0.15982(16) 0.61952(12) 0.0201(5) Uani d 1
C C2 -0.10828(17) 0.15221(18) 0.66065(14) 0.0267(5) Uani d 1
H H2 -0.1341 0.2123 0.6770 0.032 Uiso calc 1
C C3 -0.13892(19) 0.0569(2) 0.67788(15) 0.0336(6) Uani d 1
H H3 -0.1859 0.0521 0.7060 0.040 Uiso calc 1
C C4 -0.10223(19) -0.03063(19) 0.65480(15) 0.0338(6) Uani d 1
H H4 -0.1242 -0.0956 0.6665 0.041 Uiso calc 1
C C5 -0.0331(2) -0.02409(19) 0.61439(15) 0.0333(6) Uani d 1
H H5 -0.0075 -0.0846 0.5985 0.040 Uiso calc 1
C C6 -0.00137(18) 0.07029(18) 0.59724(14) 0.0284(5) Uani d 1
H H6 0.0468 0.0745 0.5702 0.034 Uiso calc 1
C C7 -0.04357(15) 0.27085(16) 0.47944(12) 0.0189(4) Uani d 1
C C8 -0.13290(16) 0.22060(18) 0.43821(13) 0.0238(5) Uani d 1
H H8 -0.1715 0.1900 0.4673 0.029 Uiso calc 1
C C9 -0.16556(16) 0.21505(18) 0.35504(14) 0.0264(5) Uani d 1
H H9 -0.2261 0.1801 0.3272 0.032 Uiso calc 1
C C10 -0.11013(18) 0.26041(18) 0.31268(14) 0.0276(5) Uani d 1
H H10 -0.1332 0.2576 0.2555 0.033 Uiso calc 1
C C11 -0.02133(19) 0.30990(19) 0.35299(14) 0.0312(6) Uani d 1
H H11 0.0168 0.3407 0.3235 0.037 Uiso calc 1
C C12 0.01247(17) 0.31487(18) 0.43633(13) 0.0255(5) Uani d 1
H H12 0.0740 0.3484 0.4639 0.031 Uiso calc 1
C C13 -0.07964(15) 0.37932(16) 0.60936(12) 0.0191(4) Uani d 1
C C14 -0.15170(16) 0.43227(17) 0.54724(14) 0.0237(5) Uani d 1
H H14 -0.1613 0.4148 0.4928 0.028 Uiso calc 1
C C15 -0.20897(16) 0.50950(17) 0.56408(15) 0.0269(5) Uani d 1
H H15 -0.2571 0.5447 0.5213 0.032 Uiso calc 1
C C16 -0.19615(16) 0.53555(17) 0.64311(15) 0.0267(5) Uani d 1
H H16 -0.2361 0.5880 0.6545 0.032 Uiso calc 1
C C17 -0.12510(16) 0.48518(17) 0.70579(14) 0.0227(5) Uani d 1
H H17 -0.1160 0.5031 0.7601 0.027 Uiso calc 1
C C18 -0.06746(15) 0.40848(16) 0.68848(13) 0.0188(4) Uani d 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Se Se -0.0929 2.2259 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
C1 P1 C7 . 103.20(10)
C1 P1 C13 . 107.09(10)
C7 P1 C13 . 104.34(10)
C1 P1 Se1 . 114.95(7)
C7 P1 Se1 . 111.86(7)
C13 P1 Se1 . 114.30(7)
C18 O1 C18 2_556 116.6(2)
C2 C1 C6 . 119.0(2)
C2 C1 P1 . 123.39(17)
C6 C1 P1 . 117.51(17)
C3 C2 C1 . 119.9(2)
C3 C2 H2 . 120.0
C1 C2 H2 . 120.0
C4 C3 C2 . 120.8(2)
C4 C3 H3 . 119.6
C2 C3 H3 . 119.6
C3 C4 C5 . 119.8(2)
C3 C4 H4 . 120.1
C5 C4 H4 . 120.1
C6 C5 C4 . 120.1(2)
C6 C5 H5 . 120.0
C4 C5 H5 . 120.0
C5 C6 C1 . 120.3(2)
C5 C6 H6 . 119.8
C1 C6 H6 . 119.8
C12 C7 C8 . 119.4(2)
C12 C7 P1 . 119.88(16)
C8 C7 P1 . 120.72(16)
C9 C8 C7 . 120.3(2)
C9 C8 H8 . 119.9
C7 C8 H8 . 119.9
C10 C9 C8 . 119.9(2)
C10 C9 H9 . 120.1
C8 C9 H9 . 120.1
C9 C10 C11 . 120.2(2)
C9 C10 H10 . 119.9
C11 C10 H10 . 119.9
C10 C11 C12 . 120.2(2)
C10 C11 H11 . 119.9
C12 C11 H11 . 119.9
C11 C12 C7 . 120.0(2)
C11 C12 H12 . 120.0
C7 C12 H12 . 120.0
C18 C13 C14 . 117.4(2)
C18 C13 P1 . 120.67(16)
C14 C13 P1 . 121.89(17)
C15 C14 C13 . 121.1(2)
C15 C14 H14 . 119.5
C13 C14 H14 . 119.5
C16 C15 C14 . 120.1(2)
C16 C15 H15 . 119.9
C14 C15 H15 . 119.9
C15 C16 C17 . 120.2(2)
C15 C16 H16 . 119.9
C17 C16 H16 . 119.9
C18 C17 C16 . 119.4(2)
C18 C17 H17 . 120.3
C16 C17 H17 . 120.3
C17 C18 O1 . 120.62(19)
C17 C18 C13 . 121.83(19)
O1 C18 C13 . 117.40(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Se1 P1 . 2.1125(6)
P1 C1 . 1.812(2)
P1 C7 . 1.819(2)
P1 C13 . 1.820(2)
O1 C18 . 1.389(2)
O1 C18 2_556 1.389(2)
C1 C2 . 1.388(3)
C1 C6 . 1.399(3)
C2 C3 . 1.385(3)
C2 H2 . 0.9500
C3 C4 . 1.372(4)
C3 H3 . 0.9500
C4 C5 . 1.385(4)
C4 H4 . 0.9500
C5 C6 . 1.380(3)
C5 H5 . 0.9500
C6 H6 . 0.9500
C7 C12 . 1.387(3)
C7 C8 . 1.394(3)
C8 C9 . 1.384(3)
C8 H8 . 0.9500
C9 C10 . 1.379(3)
C9 H9 . 0.9500
C10 C11 . 1.380(3)
C10 H10 . 0.9500
C11 C12 . 1.386(3)
C11 H11 . 0.9500
C12 H12 . 0.9500
C13 C18 . 1.398(3)
C13 C14 . 1.405(3)
C14 C15 . 1.385(3)
C14 H14 . 0.9500
C15 C16 . 1.384(3)
C15 H15 . 0.9500
C16 C17 . 1.388(3)
C16 H16 . 0.9500
C17 C18 . 1.387(3)
C17 H17 . 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C5 H5 Cg2 5_566 0.95 2.63 3.546(3) 161
C9 H9 Cg3 7_456 0.95 2.94 3.676(3) 135
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_site_symmetry_1
_geom_torsion
C7 P1 C1 C2 . -117.40(19)
C13 P1 C1 C2 . -7.6(2)
Se1 P1 C1 C2 . 120.53(18)
C7 P1 C1 C6 . 59.79(19)
C13 P1 C1 C6 . 169.57(17)
Se1 P1 C1 C6 . -62.27(18)
C6 C1 C2 C3 . -1.0(3)
P1 C1 C2 C3 . 176.11(18)
C1 C2 C3 C4 . 0.1(4)
C2 C3 C4 C5 . 0.5(4)
C3 C4 C5 C6 . -0.1(4)
C4 C5 C6 C1 . -0.9(4)
C2 C1 C6 C5 . 1.5(3)
P1 C1 C6 C5 . -175.86(18)
C1 P1 C7 C12 . -145.39(19)
C13 P1 C7 C12 . 102.79(19)
Se1 P1 C7 C12 . -21.3(2)
C1 P1 C7 C8 . 35.3(2)
C13 P1 C7 C8 . -76.5(2)
Se1 P1 C7 C8 . 159.41(16)
C12 C7 C8 C9 . -0.3(3)
P1 C7 C8 C9 . 179.05(17)
C7 C8 C9 C10 . -0.7(3)
C8 C9 C10 C11 . 1.1(4)
C9 C10 C11 C12 . -0.4(4)
C10 C11 C12 C7 . -0.6(4)
C8 C7 C12 C11 . 1.0(4)
P1 C7 C12 C11 . -178.38(19)
C1 P1 C13 C18 . 71.55(19)
C7 P1 C13 C18 . -179.48(17)
Se1 P1 C13 C18 . -57.00(18)
C1 P1 C13 C14 . -111.23(18)
C7 P1 C13 C14 . -2.2(2)
Se1 P1 C13 C14 . 120.23(16)
C18 C13 C14 C15 . -0.7(3)
P1 C13 C14 C15 . -177.99(17)
C13 C14 C15 C16 . -0.3(3)
C14 C15 C16 C17 . 0.7(3)
C15 C16 C17 C18 . -0.2(3)
C16 C17 C18 O1 . -176.18(19)
C16 C17 C18 C13 . -0.8(3)
C18 O1 C18 C17 2_556 -51.46(16)
C18 O1 C18 C13 2_556 132.9(2)
C14 C13 C18 C17 . 1.2(3)
P1 C13 C18 C17 . 178.56(16)
C14 C13 C18 O1 . 176.74(17)
P1 C13 C18 O1 . -5.9(3)
