#------------------------------------------------------------------------------
#$Date: 2019-10-24 05:22:15 +0300 (Thu, 24 Oct 2019) $
#$Revision: 219478 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/89/7058906.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_7058906
loop_
_publ_author_name
'Arp, Fabian Felix'
'Ahn, Shin Hye'
'Bhuvanesh, Nattamai'
'Bluemel, Janet'
_publ_section_title
;
 Selective Synthesis and Stabilization of Peroxides via Phosphine Oxides
;
_journal_name_full               'New Journal of Chemistry'
_journal_paper_doi               10.1039/C9NJ04858H
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C5 H10 O4'
_chemical_formula_sum            'C5 H10 O4'
_chemical_formula_weight         134.13
_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_Hall           'P 4nw 2abw'
_space_group_name_H-M_alt        'P 43 21 2'
_symmetry_space_group_name_Hall  'P 4nw 2abw'
_symmetry_space_group_name_H-M   'P 43 21 2'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-12-10
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_audit_update_record
;
2019-10-14 deposited with the CCDC.    2019-10-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9845(4)
_cell_length_b                   8.9845(4)
_cell_length_c                   8.5007(5)
_cell_measurement_reflns_used    8034
_cell_measurement_temperature    110.15
_cell_measurement_theta_max      60.511
_cell_measurement_theta_min      6.968
_cell_volume                     686.19(6)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX 3 (Bruker-AXS, Madison WI)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      110.15
_diffrn_measured_fraction_theta_full 0.838
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker GADDS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_Laue_measured_fraction_full 0.838
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            15337
_diffrn_reflns_point_group_measured_fraction_full 0.833
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         60.489
_diffrn_reflns_theta_min         6.970
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.975
_exptl_absorpt_correction_T_max  0.7388
_exptl_absorpt_correction_T_min  0.6510
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.1018 before and 0.0654 after correction.
The Ratio of minimum to maximum transmission is 0.8812.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.116
_refine_diff_density_min         -0.092
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details
;
 Flack x determined using 174 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.46(10)
_refine_ls_extinction_coef       0.037(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.195
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     45
_refine_ls_number_reflns         518
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.195
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0246
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0189P)²+0.1611P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0555
_refine_ls_wR_factor_ref         0.0557
_reflns_Friedel_coverage         0.542
_reflns_Friedel_fraction_full    0.824
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                491
_reflns_number_total             518
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9nj04858h2.cif
_cod_data_source_block           temp
_cod_original_cell_volume        686.19(7)
_cod_database_code               7058906
_shelxl_version_number           2014-3
_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.
;
_shelx_estimated_absorpt_t_max   0.909
_shelx_estimated_absorpt_t_min   0.844
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Fixed Sof: H1A(0.5) H1B(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
3.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C)
3.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_file
;
TITL temp in P4(3)2(1)2
REM Best SHELXD solution FINAL CC 88.00
REM Fragments: 5
CELL 1.54178 8.9845 8.9845 8.5007 90 90 90
ZERR 4 0.00035 0.00035 0.0005 0 0 0
LATT -1
SYMM -X,-Y,0.5+Z
SYMM 0.5-Y,0.5+X,0.75+Z
SYMM 0.5+Y,0.5-X,0.25+Z
SYMM 0.5-X,0.5+Y,0.75-Z
SYMM 0.5+X,0.5-Y,0.25-Z
SYMM +Y,+X,-Z
SYMM -Y,-X,0.5-Z
SFAC C H O
UNIT 20 40 16

L.S. 10
PLAN  7
SIZE 0.18 0.13 0.1
TEMP -163
bond $H
more -1
wpdb -1
htab
conf
fmap 2 53
acta
OMIT 0 1 1
OMIT 2 2 2
OMIT 0 2 0
OMIT 0 1 2
REM <olex2.extras>
REM <HklSrc "%.\\temp.hkl">
REM </olex2.extras>

WGHT    0.018900    0.161100
EXTI    0.037029
FVAR       0.53159
O1    3    0.699060    0.308420    0.163904    11.00000    0.03570    0.02126 =
         0.05285    0.00189   -0.02010    0.00146
O2    3    0.637741    0.059072    0.131129    11.00000    0.02313    0.02368 =
         0.02067    0.00237   -0.00477   -0.00393
AFIX 147
H2    2    0.574585    0.076828    0.060725    11.00000   -1.50000
AFIX   0
C1    1    0.868448    0.131552    0.250000    10.50000    0.01952    0.01952 =
         0.01920    0.00079    0.00079    0.00071
AFIX  23
H1A   2    0.970982    0.143547    0.209277    10.50000   -1.20000
H1B   2    0.856455    0.029017    0.290723    10.50000   -1.20000
AFIX   0
C2    1    0.753930    0.164731    0.122235    11.00000    0.01997    0.02248 =
         0.02321    0.00296   -0.00029   -0.00308
C3    1    0.812456    0.179609   -0.043370    11.00000    0.02817    0.09451 =
         0.02353    0.01759   -0.00334   -0.01470
AFIX 137
H3A   2    0.851891    0.083537   -0.078627    11.00000   -1.50000
H3B   2    0.891941    0.254275   -0.045681    11.00000   -1.50000
H3C   2    0.731552    0.210678   -0.113374    11.00000   -1.50000
AFIX   0
HKLF 4

REM  temp in P4(3)2(1)2
REM R1 =  0.0246 for     491 Fo > 4sig(Fo)  and  0.0261 for all     518 data
REM     45 parameters refined using      0 restraints

END

WGHT      0.0189      0.1611

REM Instructions for potential hydrogen bonds
EQIV $1 -y+1/2, x-1/2, z-1/4
HTAB O2 O2_$1
EQIV $2 x+1/2, -y+1/2, -z+1/4
HTAB C1 O1_$2
EQIV $3 y+1/2, -x+1/2, z+1/4
HTAB C1 O1_$3

REM Highest difference peak  0.116,  deepest hole -0.092,  1-sigma level  0.026
Q1    1   0.8080  0.1530  0.1892  11.00000  0.05    0.12
Q2    1   0.9038  0.1857 -0.0706  11.00000  0.05    0.10
Q3    1   0.7423  0.1870 -0.1187  11.00000  0.05    0.09
Q4    1   0.8804  0.3236 -0.0193  11.00000  0.05    0.09
Q5    1   0.6164  0.3271  0.1147  11.00000  0.05    0.09
Q6    1   0.5260 -0.0716  0.1119  11.00000  0.05    0.08
Q7    1   0.7898  0.0137  0.3580  11.00000  0.05    0.08
;
_shelx_res_checksum              84934
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
O1 O 0.69906(16) 0.30842(15) 0.16390(17) 0.0366(5) Uani 1 1 d . . .
O2 O 0.63774(14) 0.05907(13) 0.13113(15) 0.0225(4) Uani 1 1 d . . .
H2 H 0.5746 0.0768 0.0607 0.034 Uiso 1 1 calc GR . .
C1 C 0.86845(19) 0.13155(19) 0.2500 0.0194(6) Uani 1 2 d S T P
H1A H 0.9710 0.1435 0.2093 0.023 Uiso 0.5 1 calc R . .
H1B H 0.8565 0.0290 0.2907 0.023 Uiso 0.5 1 calc R . .
C2 C 0.7539(2) 0.1647(2) 0.1222(2) 0.0219(5) Uani 1 1 d . . .
C3 C 0.8125(3) 0.1796(3) -0.0434(2) 0.0487(8) Uani 1 1 d . . .
H3A H 0.8519 0.0835 -0.0786 0.073 Uiso 1 1 calc GR . .
H3B H 0.8919 0.2543 -0.0457 0.073 Uiso 1 1 calc GR . .
H3C H 0.7316 0.2107 -0.1134 0.073 Uiso 1 1 calc GR . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0357(9) 0.0213(8) 0.0529(8) 0.0019(7) -0.0201(7) 0.0015(6)
O2 0.0231(7) 0.0237(7) 0.0207(7) 0.0024(6) -0.0048(6) -0.0039(6)
C1 0.0195(8) 0.0195(8) 0.0192(13) 0.0008(9) 0.0008(9) 0.0007(11)
C2 0.0200(9) 0.0225(10) 0.0232(10) 0.0030(8) -0.0003(8) -0.0031(8)
C3 0.0282(12) 0.095(2) 0.0235(12) 0.0176(12) -0.0033(9) -0.0147(12)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 '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
C2 O1 O1 102.84(11) . 8_665
C2 O2 H2 109.5 . .
H1A C1 H1B 109.0 . .
C2 C1 H1A 110.9 8_665 .
C2 C1 H1A 110.9 . .
C2 C1 H1B 110.9 8_665 .
C2 C1 H1B 110.9 . .
C2 C1 C2 104.1(2) . 8_665
O1 C2 C1 103.48(15) . .
O1 C2 C3 105.78(17) . .
O2 C2 O1 109.84(15) . .
O2 C2 C1 109.20(13) . .
O2 C2 C3 111.53(18) . .
C3 C2 C1 116.52(15) . .
C2 C3 H3A 109.5 . .
C2 C3 H3B 109.5 . .
C2 C3 H3C 109.5 . .
H3A C3 H3B 109.5 . .
H3A C3 H3C 109.5 . .
H3B C3 H3C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 O1 1.467(3) 8_665
O1 C2 1.427(2) .
O2 H2 0.8400 .
O2 C2 1.413(2) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C1 C2 1.525(2) .
C1 C2 1.525(2) 8_665
C2 C3 1.509(3) .
C3 H3A 0.9800 .
C3 H3B 0.9800 .
C3 H3C 0.9800 .
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
O1 O1 C2 O2 77.83(18) 8_665
O1 O1 C2 C1 -38.66(17) 8_665
O1 O1 C2 C3 -161.69(16) 8_665
C2 C1 C2 O1 14.93(8) 8_665
C2 C1 C2 O2 -102.01(15) 8_665
C2 C1 C2 C3 130.54(19) 8_665
