#------------------------------------------------------------------------------
#$Date: 2019-08-30 03:45:25 +0200 (vie 30 de ago de 2019) $
#$Revision: 217859 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/35/7233577.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_7233577
loop_
_publ_author_name
'Hwang, Kuo Chu'
'Sagadevan, Arunachalam'
'Kundu, Pradip'
_publ_section_title
;
 Sustainable Room Temperature Conversion of p-Xylene to Terephthalic Acid
 using Ozone and UV Irradiation
;
_journal_name_full               'Green Chemistry'
_journal_paper_doi               10.1039/C9GC02095K
_journal_year                    2019
_chemical_formula_sum            'C12 H14 O4'
_chemical_formula_weight         222.23
_chemical_name_systematic        'diethyl terephthalate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2014-11-18 deposited with the CCDC.    2019-08-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.854(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.206(2)
_cell_length_b                   15.399(9)
_cell_length_c                   9.109(5)
_cell_measurement_reflns_used    218
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.8073
_cell_measurement_theta_min      2.6003
_cell_volume                     589.2(5)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4463
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.391
_diffrn_reflns_theta_min         2.600
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_correction_T_min  0.8135
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Lump
_exptl_crystal_F_000             236
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane-ethylacetate'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     74
_refine_ls_number_reflns         1173
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.1046
_refine_ls_R_factor_gt           0.0536
_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)+(0.0639P)²+0.1292P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1257
_refine_ls_wR_factor_ref         0.1521
_reflns_Friedel_coverage         0.000
_reflns_number_gt                659
_reflns_number_total             1173
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9gc02095k2.cif
_cod_data_source_block           mo_141114_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_cell_volume        589.2(6)
_cod_database_code               7233577
_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           2014/6
_shelx_res_file
;
TITL mo_141114_0m.res in P2(1)/n
CELL  0.71073   4.2061  15.3985   9.1091   90.000   92.854   90.000
ZERR    2.000   0.0024   0.0087   0.0051    0.000    0.010    0.000
LATT 1
SYMM 1/2-X, 1/2+Y, 1/2-Z
SFAC C  O  H
UNIT 24  8  28
L.S. 4
ACTA
BOND $H
FMAP 2
PLAN 5
TEMP 23.000
WGHT    0.063900    0.129200
FVAR       1.27070
C1    1    0.357665    0.570332    0.931445    11.00000    0.07291    0.05679 =
         0.06812    0.01407   -0.00151    0.00219
AFIX  43
H1    3    0.261074    0.617817    0.884550    11.00000   -1.20000
AFIX   0
C2    1    0.513720    0.509826    0.850805    11.00000    0.07174    0.06492 =
         0.05698    0.01188    0.00051   -0.00358
AFIX  43
H2    3    0.522913    0.516816    0.749695    11.00000   -1.20000
AFIX   0
C3    1    0.656619    0.438933    0.918339    11.00000    0.05371    0.05348 =
         0.06101    0.00652   -0.00218   -0.00957
C4    1    0.829834    0.372179    0.835867    11.00000    0.05924    0.05762 =
         0.07161    0.00814   -0.00178   -0.00784
C5    1    0.988317    0.328197    0.601214    11.00000    0.07763    0.06934 =
         0.08579   -0.00934    0.00108    0.01050
AFIX  23
H5A   3    0.877716    0.272900    0.598792    11.00000   -1.20000
H5B   3    1.204798    0.318792    0.639651    11.00000   -1.20000
AFIX   0
C6    1    0.988860    0.365580    0.453043    11.00000    0.14543    0.09713 =
         0.09083    0.00371    0.03625    0.03070
AFIX 137
H6A   3    0.774459    0.378798    0.419285    11.00000   -1.50000
H6B   3    1.078878    0.324582    0.387436    11.00000   -1.50000
H6C   3    1.113598    0.417816    0.455476    11.00000   -1.50000
AFIX   0
O1    2    0.956270    0.310053    0.891360    11.00000    0.10651    0.06954 =
         0.09251    0.01566    0.00188    0.01918
O2    2    0.827194    0.389387    0.693006    11.00000    0.08043    0.06791 =
         0.06762   -0.00027    0.00365    0.01029
HKLF 4

REM  mo_141114_0m.res in P2(1)/n
REM R1 =  0.0536 for     659 Fo > 4sig(Fo)  and  0.1046 for all    1173 data
REM     74 parameters refined using      0 restraints

END

WGHT      0.0638      0.1293

REM Highest difference peak  0.149,  deepest hole -0.144,  1-sigma level  0.034
Q1    1   0.9835  0.4342  0.4154  11.00000  0.05    0.15
Q2    1   1.2693  0.4303  0.5206  11.00000  0.05    0.13
Q3    1   1.1054  0.2711  0.6654  11.00000  0.05    0.12
Q4    1   0.7468  0.3049  0.8395  11.00000  0.05    0.10
Q5    1   0.0835  0.6099  0.8726  11.00000  0.05    0.09
;
_shelx_res_checksum              22976
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.3577(6) 0.57033(15) 0.9314(3) 0.0661(7) Uani 1 1 d . .
H1 H 0.2611 0.6178 0.8845 0.079 Uiso 1 1 calc R U
C2 C 0.5137(6) 0.50983(15) 0.8508(3) 0.0646(7) Uani 1 1 d . .
H2 H 0.5229 0.5168 0.7497 0.078 Uiso 1 1 calc R U
C3 C 0.6566(5) 0.43893(14) 0.9183(2) 0.0562(6) Uani 1 1 d . .
C4 C 0.8298(6) 0.37218(15) 0.8359(3) 0.0630(7) Uani 1 1 d . .
C5 C 0.9883(7) 0.32820(17) 0.6012(3) 0.0777(8) Uani 1 1 d . .
H5A H 0.8777 0.2729 0.5988 0.093 Uiso 1 1 calc R U
H5B H 1.2048 0.3188 0.6397 0.093 Uiso 1 1 calc R U
C6 C 0.9889(9) 0.3656(2) 0.4530(3) 0.1101(12) Uani 1 1 d . .
H6A H 0.7745 0.3788 0.4193 0.165 Uiso 1 1 calc R U
H6B H 1.0789 0.3246 0.3874 0.165 Uiso 1 1 calc R U
H6C H 1.1136 0.4178 0.4555 0.165 Uiso 1 1 calc R U
O1 O 0.9563(5) 0.31005(12) 0.8914(2) 0.0896(7) Uani 1 1 d . .
O2 O 0.8272(4) 0.38939(10) 0.69301(18) 0.0720(6) Uani 1 1 d . .
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
C1 0.0729(19) 0.0568(14) 0.0681(16) 0.0141(12) -0.0015(13) 0.0022(12)
C2 0.0717(18) 0.0649(15) 0.0570(13) 0.0119(12) 0.0005(12) -0.0036(12)
C3 0.0537(15) 0.0535(13) 0.0610(14) 0.0065(10) -0.0022(11) -0.0096(10)
C4 0.0592(16) 0.0576(14) 0.0716(17) 0.0081(12) -0.0018(13) -0.0078(12)
C5 0.078(2) 0.0693(16) 0.0858(19) -0.0093(14) 0.0011(15) 0.0105(14)
C6 0.145(3) 0.097(2) 0.091(2) 0.0037(18) 0.036(2) 0.031(2)
O1 0.1065(17) 0.0695(11) 0.0925(13) 0.0157(10) 0.0019(11) 0.0192(11)
O2 0.0804(13) 0.0679(11) 0.0676(11) -0.0003(8) 0.0037(9) 0.0103(9)
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'
O O 0.0106 0.0060 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 C3 120.4(2) . 3_667
C2 C1 H1 119.8 . .
C3 C1 H1 119.8 3_667 .
C1 C2 C3 120.6(2) . .
C1 C2 H2 119.7 . .
C3 C2 H2 119.7 . .
C2 C3 C1 119.0(2) . 3_667
C2 C3 C4 122.5(2) . .
C1 C3 C4 118.5(2) 3_667 .
O1 C4 O2 123.8(2) . .
O1 C4 C3 124.0(2) . .
O2 C4 C3 112.2(2) . .
O2 C5 C6 107.3(2) . .
O2 C5 H5A 110.3 . .
C6 C5 H5A 110.3 . .
O2 C5 H5B 110.3 . .
C6 C5 H5B 110.3 . .
H5A C5 H5B 108.5 . .
C5 C6 H6A 109.5 . .
C5 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C5 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
C4 O2 C5 117.0(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.374(3) .
C1 C3 1.380(3) 3_667
C1 H1 0.9300 .
C2 C3 1.376(3) .
C2 H2 0.9300 .
C3 C1 1.380(3) 3_667
C3 C4 1.485(3) .
C4 O1 1.194(3) .
C4 O2 1.328(3) .
C5 O2 1.450(3) .
C5 C6 1.467(4) .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C6 H6A 0.9600 .
C6 H6B 0.9600 .
C6 H6C 0.9600 .
