#------------------------------------------------------------------------------
#$Date: 2025-08-21 13:21:36 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301847 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/41/7014148.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_7014148
loop_
_publ_author_name
'Monkowius, Uwe V.'
'Nogai, Stefan'
'Schmidbaur, Hubert'
_publ_section_title
;
 Unsuccessful/successful attempts to produce
 penta(heteroaryl)-phosphoranes/-arsoranes R5E (E = P, As; R = 2-furyl,
 2-thienyl).
;
_journal_issue                   10
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              1610
_journal_page_last               1617
_journal_paper_doi               10.1039/b401988a
_journal_year                    2004
_chemical_formula_sum            'C12 H9 As O3'
_chemical_formula_weight         276.11
_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   difmap
_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            4
_cell_length_a                   7.79090(10)
_cell_length_b                   8.16180(10)
_cell_length_c                   17.2498(3)
_cell_measurement_reflns_used    29571
_cell_measurement_temperature    143(2)
_cell_volume                     1096.88(3)
_computing_cell_refinement       DENZO
_computing_data_collection       XPRESS
_computing_data_reduction        SCALEPACK
_computing_molecular_graphics    SHELXTL-PLUS
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      143(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'NONIUS DIP 2020'
_diffrn_measurement_method       phi-rotation
_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  0.045
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            29571
_diffrn_reflns_theta_full        26.73
_diffrn_reflns_theta_max         26.73
_diffrn_reflns_theta_min         3.44
_exptl_absorpt_coefficient_mu    3.086
_exptl_absorpt_correction_T_max  0.892
_exptl_absorpt_correction_T_min  0.634
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details
;
Platon Delabs
(See: Walker, N. & Stuart, D. (1983) Acta Cryst. A39, 158-166)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.672
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.500
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.026(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2263
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.0178
_refine_ls_R_factor_gt           0.0177
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0248P)²+0.1032P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0467
_refine_ls_wR_factor_ref         0.0468
_reflns_number_gt                2243
_reflns_number_total             2263
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b401988a.txt
_cod_data_source_block           uwe34
_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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7014148
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
_atom_site_disorder_assembly
_atom_site_disorder_group
As1 As 0.20565(2) 0.192668(19) 0.050398(9) 0.02061(7) Uani 1 1 d . . .
C11 C 0.0668(2) 0.0809(2) 0.12711(10) 0.0223(3) Uani 1 1 d . . .
O12 O 0.14017(18) -0.00783(18) 0.18599(8) 0.0346(3) Uani 1 1 d . . .
C13 C 0.0065(3) -0.0664(3) 0.23041(12) 0.0365(5) Uani 1 1 d . . .
H13 H 0.037(4) -0.125(4) 0.2707(19) 0.062(10) Uiso 1 1 d . . .
C14 C -0.1433(3) -0.0198(3) 0.20127(11) 0.0317(4) Uani 1 1 d . . .
H14 H -0.250(4) -0.041(3) 0.2197(15) 0.045(7) Uiso 1 1 d . . .
C15 C -0.1050(3) 0.0756(2) 0.13351(10) 0.0275(4) Uani 1 1 d . . .
H15 H -0.181(3) 0.126(3) 0.1012(14) 0.036(6) Uiso 1 1 d . . .
C21 C 0.3616(2) 0.3089(2) 0.11804(10) 0.0220(3) Uani 1 1 d . . .
O21 O 0.44550(19) 0.22897(16) 0.17683(8) 0.0300(3) Uani 1 1 d . . .
C23 C 0.5569(3) 0.3402(3) 0.20876(12) 0.0317(4) Uani 1 1 d . . .
H23 H 0.619(3) 0.297(3) 0.2525(14) 0.033(6) Uiso 1 1 d . . .
C24 C 0.5457(3) 0.4847(3) 0.17212(12) 0.0319(4) Uani 1 1 d . . .
H24 H 0.610(4) 0.571(4) 0.1835(15) 0.041(7) Uiso 1 1 d . . .
C25 C 0.4180(3) 0.4651(2) 0.11301(12) 0.0290(4) Uani 1 1 d . . .
H25 H 0.380(3) 0.540(3) 0.0785(13) 0.026(5) Uiso 1 1 d . . .
C31 C 0.3617(2) 0.0174(2) 0.02368(10) 0.0227(3) Uani 1 1 d . . .
O32 O 0.3821(2) -0.01367(18) -0.05385(8) 0.0374(3) Uani 1 1 d . . .
C33 C 0.5050(4) -0.1347(3) -0.05964(16) 0.0442(6) Uani 1 1 d . . .
H33 H 0.534(4) -0.158(4) -0.1104(18) 0.054(8) Uiso 1 1 d . . .
C34 C 0.5600(3) -0.1767(3) 0.00988(17) 0.0437(5) Uani 1 1 d . . .
H34 H 0.640(4) -0.250(4) 0.0178(17) 0.053(8) Uiso 1 1 d . . .
C35 C 0.4700(3) -0.0785(2) 0.06555(11) 0.0288(4) Uani 1 1 d D . .
H35 H 0.481(4) -0.076(4) 0.1176(11) 0.068(10) Uiso 1 1 d 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
As As 0.0499 2.0058 '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 As1 C21 96.43(8) . . ?
C31 As1 C11 99.55(8) . . ?
C21 As1 C11 99.77(8) . . ?
C15 C11 O12 109.70(17) . . ?
C15 C11 As1 128.89(15) . . ?
O12 C11 As1 121.41(13) . . ?
C11 O12 C13 106.22(15) . . ?
C14 C13 O12 110.77(17) . . ?
C14 C13 H13 134(2) . . ?
O12 C13 H13 115(2) . . ?
C13 C14 C15 106.36(17) . . ?
C13 C14 H14 128.2(18) . . ?
C15 C14 H14 125.4(18) . . ?
C11 C15 C14 106.94(17) . . ?
C11 C15 H15 125.6(17) . . ?
C14 C15 H15 127.4(16) . . ?
C25 C21 O21 109.96(16) . . ?
C25 C21 As1 128.96(15) . . ?
O21 C21 As1 120.80(13) . . ?
C23 O21 C21 106.47(15) . . ?
C24 C23 O21 110.60(18) . . ?
C24 C23 H23 136.2(15) . . ?
O21 C23 H23 113.1(15) . . ?
C23 C24 C25 106.40(17) . . ?
C23 C24 H24 123.8(18) . . ?
C25 C24 H24 129.8(18) . . ?
C21 C25 C24 106.57(17) . . ?
C21 C25 H25 125.3(15) . . ?
C24 C25 H25 128.1(15) . . ?
C35 C31 O32 109.87(17) . . ?
C35 C31 As1 133.63(14) . . ?
O32 C31 As1 116.28(13) . . ?
C31 O32 C33 106.49(18) . . ?
C34 C33 O32 110.3(2) . . ?
C34 C33 H33 137(2) . . ?
O32 C33 H33 112.6(19) . . ?
C33 C34 C35 107.7(2) . . ?
C33 C34 H34 123(2) . . ?
C35 C34 H34 129(2) . . ?
C31 C35 C34 105.66(19) . . ?
C31 C35 H35 125(2) . . ?
C34 C35 H35 129(2) . . ?
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
As1 C31 1.9330(19) . ?
As1 C21 1.9332(18) . ?
As1 C11 1.9374(18) . ?
C11 C15 1.344(3) . ?
C11 O12 1.372(2) . ?
O12 C13 1.379(2) . ?
C13 C14 1.326(3) . ?
C13 H13 0.88(3) . ?
C14 C15 1.435(3) . ?
C14 H14 0.91(3) . ?
C15 H15 0.91(3) . ?
C21 C25 1.351(3) . ?
C21 O21 1.372(2) . ?
O21 C23 1.371(2) . ?
C23 C24 1.341(3) . ?
C23 H23 0.97(2) . ?
C24 C25 1.434(3) . ?
C24 H24 0.88(3) . ?
C25 H25 0.91(2) . ?
C31 C35 1.359(3) . ?
C31 O32 1.370(2) . ?
O32 C33 1.379(3) . ?
C33 C34 1.319(4) . ?
C33 H33 0.92(3) . ?
C34 C35 1.434(3) . ?
C34 H34 0.87(3) . ?
C35 H35 0.902(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
C31 As1 C11 C15 -132.42(19) . . . . ?
C21 As1 C11 C15 129.29(19) . . . . ?
C31 As1 C11 O12 48.04(16) . . . . ?
C21 As1 C11 O12 -50.26(16) . . . . ?
C15 C11 O12 C13 -1.1(2) . . . . ?
As1 C11 O12 C13 178.49(15) . . . . ?
C11 O12 C13 C14 0.7(2) . . . . ?
O12 C13 C14 C15 -0.1(3) . . . . ?
O12 C11 C15 C14 1.1(2) . . . . ?
As1 C11 C15 C14 -178.49(14) . . . . ?
C13 C14 C15 C11 -0.6(2) . . . . ?
C31 As1 C21 C25 121.85(18) . . . . ?
C11 As1 C21 C25 -137.26(18) . . . . ?
C31 As1 C21 O21 -51.36(15) . . . . ?
C11 As1 C21 O21 49.52(15) . . . . ?
C25 C21 O21 C23 0.0(2) . . . . ?
As1 C21 O21 C23 174.41(13) . . . . ?
C21 O21 C23 C24 -0.2(2) . . . . ?
O21 C23 C24 C25 0.3(2) . . . . ?
O21 C21 C25 C24 0.2(2) . . . . ?
As1 C21 C25 C24 -173.63(14) . . . . ?
C23 C24 C25 C21 -0.3(2) . . . . ?
C21 As1 C31 C35 45.3(2) . . . . ?
C11 As1 C31 C35 -55.8(2) . . . . ?
C21 As1 C31 O32 -128.71(13) . . . . ?
C11 As1 C31 O32 130.21(14) . . . . ?
C35 C31 O32 C33 1.1(2) . . . . ?
As1 C31 O32 C33 176.48(14) . . . . ?
C31 O32 C33 C34 -0.5(2) . . . . ?
O32 C33 C34 C35 -0.2(3) . . . . ?
O32 C31 C35 C34 -1.2(2) . . . . ?
As1 C31 C35 C34 -175.48(16) . . . . ?
C33 C34 C35 C31 0.8(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 42635
2 PubChem 46841
