data_global

_journal_coden_Cambridge         182
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

loop_
_publ_author_name
'Julia Perez-Prieto'
'Abdeslem Ben-Tama'
'M. Consuelo Cuquerella'
'de Arellano, Carmen Ramirez'
'El Moncef, Abdelkarim'
'Salah-Eddine Stiriba'
'Elena Zaballos'

_publ_contact_author_name        'Julia Perez-Prieto'
_publ_contact_author_email       JULIA.PEREZ@UV.ES

_publ_section_title              
;
Efficient Ultraviolet-Light
Energy Dissipation by an Aromatic Ketone
;

# Attachment 'TMBZ21c.cif'

data_TMBZ_elmoncefp21c
_database_code_depnum_ccdc_archive 'CCDC 743200'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 O6'
_chemical_formula_weight         330.32

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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'

_cell_length_a                   8.4629(17)
_cell_length_b                   11.351(2)
_cell_length_c                   18.242(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.15(3)
_cell_angle_gamma                90.00
_cell_volume                     1611.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9400
_cell_measurement_theta_min      2.4072
_cell_measurement_theta_max      32.2661

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.949
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May 6 2009,17:20:42)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 16.0267
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            32390
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_sigmaI/netI    0.0504
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         32.34
_reflns_number_total             5476
_reflns_number_gt                3531
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Oxford Diff., 2009)'
_computing_cell_refinement       'CrysAlisPro (Oxford Diff., 2009)'
_computing_data_reduction        'CrysAlisPro (Oxford Diff., 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'CrystalMaker 2.1.5 (1994-2009)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
Methyl groups hydrogen atoms refined as rigid, others riding
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0528P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5476
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.0946
_refine_ls_wR_factor_gt          0.0902
_refine_ls_goodness_of_fit_ref   0.894
_refine_ls_restrained_S_all      0.894
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O1 O 0.15689(9) 0.62478(6) 0.28408(4) 0.02451(17) Uani 1 1 d . . .
O2 O 0.47529(9) 0.48355(7) 0.31088(4) 0.02452(17) Uani 1 1 d . . .
O3 O 0.20792(9) 0.28452(6) 0.23416(4) 0.02161(16) Uani 1 1 d . . .
O4 O -0.20168(9) 0.32218(7) -0.03084(4) 0.02287(17) Uani 1 1 d . . .
O5 O 0.05026(9) 0.40367(7) 0.34923(4) 0.02419(17) Uani 1 1 d . . .
O6 O 0.37144(9) 0.20670(7) 0.59154(4) 0.02312(17) Uani 1 1 d . . .
C1 C 0.18169(13) 0.52385(9) 0.26722(6) 0.0180(2) Uani 1 1 d . . .
C2 C 0.34709(13) 0.46542(9) 0.32498(6) 0.0178(2) Uani 1 1 d . . .
C11 C 0.07426(12) 0.46735(9) 0.19152(6) 0.0171(2) Uani 1 1 d . . .
C12 C 0.09144(12) 0.34804(9) 0.17425(6) 0.0166(2) Uani 1 1 d . . .
C13 C -0.00716(13) 0.30208(9) 0.09997(6) 0.0179(2) Uani 1 1 d . . .
H13 H 0.0027 0.2213 0.0889 0.022 Uiso 1 1 calc R . .
C14 C -0.12093(12) 0.37503(9) 0.04150(6) 0.0182(2) Uani 1 1 d . . .
C15 C -0.14501(13) 0.49214(9) 0.05761(6) 0.0212(2) Uani 1 1 d . . .
H15 H -0.2259 0.5406 0.0181 0.025 Uiso 1 1 calc R . .
C16 C -0.04801(13) 0.53577(9) 0.13255(6) 0.0204(2) Uani 1 1 d . . .
H16 H -0.0649 0.6151 0.1445 0.024 Uiso 1 1 calc R . .
C17 C 0.23025(14) 0.16248(9) 0.22020(7) 0.0232(2) Uani 1 1 d . . .
H17A H 0.1202 0.1213 0.2053 0.035 Uiso 1 1 calc R . .
H17B H 0.3149 0.1273 0.2688 0.035 Uiso 1 1 calc R . .
H17C H 0.2708 0.1555 0.1769 0.035 Uiso 1 1 calc R . .
C18 C -0.33146(15) 0.38854(11) -0.09190(6) 0.0291(3) Uani 1 1 d . . .
H18A H -0.4232 0.4092 -0.0741 0.044 Uiso 1 1 calc R . .
H18B H -0.3793 0.3411 -0.1406 0.044 Uiso 1 1 calc R . .
H18C H -0.2807 0.4607 -0.1027 0.044 Uiso 1 1 calc R . .
C21 C 0.35228(12) 0.40333(8) 0.39667(6) 0.0164(2) Uani 1 1 d . . .
C22 C 0.20202(12) 0.36976(9) 0.40753(6) 0.0170(2) Uani 1 1 d . . .
C23 C 0.21376(13) 0.30489(9) 0.47356(6) 0.0191(2) Uani 1 1 d . . .
H23 H 0.1125 0.2813 0.4802 0.023 Uiso 1 1 calc R . .
C24 C 0.37528(13) 0.27408(9) 0.53058(6) 0.0179(2) Uani 1 1 d . . .
C25 C 0.52563(13) 0.30983(9) 0.52275(6) 0.0191(2) Uani 1 1 d . . .
H25 H 0.6353 0.2915 0.5626 0.023 Uiso 1 1 calc R . .
C26 C 0.51079(13) 0.37254(9) 0.45548(6) 0.0185(2) Uani 1 1 d . . .
H26 H 0.6125 0.3956 0.4491 0.022 Uiso 1 1 calc R . .
C27 C -0.10632(13) 0.37276(11) 0.35681(7) 0.0282(2) Uani 1 1 d . . .
H27A H -0.1153 0.2868 0.3584 0.042 Uiso 1 1 calc R . .
H27B H -0.2040 0.4037 0.3111 0.042 Uiso 1 1 calc R . .
H27C H -0.1070 0.4066 0.4061 0.042 Uiso 1 1 calc R . .
C28 C 0.53260(14) 0.17394(11) 0.65376(6) 0.0273(2) Uani 1 1 d . . .
H28A H 0.5994 0.1268 0.6311 0.041 Uiso 1 1 calc R . .
H28B H 0.5110 0.1276 0.6942 0.041 Uiso 1 1 calc R . .
H28C H 0.5972 0.2451 0.6784 0.041 Uiso 1 1 calc R . .

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 0.0241(4) 0.0182(4) 0.0293(4) -0.0041(3) 0.0083(3) -0.0010(3)
O2 0.0193(4) 0.0315(4) 0.0251(4) 0.0005(3) 0.0112(3) -0.0039(3)
O3 0.0228(4) 0.0168(4) 0.0192(4) 0.0007(3) 0.0018(3) 0.0030(3)
O4 0.0205(4) 0.0284(4) 0.0156(4) -0.0004(3) 0.0027(3) 0.0017(3)
O5 0.0128(3) 0.0336(4) 0.0239(4) 0.0075(3) 0.0049(3) -0.0011(3)
O6 0.0196(4) 0.0285(4) 0.0189(4) 0.0054(3) 0.0050(3) -0.0020(3)
C1 0.0174(5) 0.0177(5) 0.0208(5) 0.0006(4) 0.0097(4) -0.0024(4)
C2 0.0182(5) 0.0165(4) 0.0188(5) -0.0036(4) 0.0072(4) -0.0031(4)
C11 0.0171(5) 0.0171(5) 0.0172(5) 0.0014(4) 0.0068(4) -0.0012(4)
C12 0.0151(5) 0.0174(5) 0.0175(5) 0.0025(4) 0.0066(4) 0.0004(4)
C13 0.0177(5) 0.0172(5) 0.0196(5) -0.0013(4) 0.0080(4) -0.0002(4)
C14 0.0154(5) 0.0231(5) 0.0166(5) 0.0001(4) 0.0069(4) -0.0018(4)
C15 0.0188(5) 0.0220(5) 0.0206(5) 0.0056(4) 0.0054(4) 0.0025(4)
C16 0.0215(5) 0.0158(5) 0.0248(5) 0.0025(4) 0.0102(4) 0.0015(4)
C17 0.0223(5) 0.0158(5) 0.0284(6) 0.0019(4) 0.0066(4) 0.0025(4)
C18 0.0241(6) 0.0386(7) 0.0190(5) 0.0036(5) 0.0025(4) 0.0057(5)
C21 0.0162(5) 0.0161(5) 0.0171(5) -0.0026(4) 0.0067(4) -0.0019(4)
C22 0.0135(5) 0.0181(5) 0.0182(5) -0.0026(4) 0.0048(4) -0.0007(4)
C23 0.0161(5) 0.0214(5) 0.0206(5) -0.0008(4) 0.0080(4) -0.0024(4)
C24 0.0202(5) 0.0166(5) 0.0172(5) -0.0016(4) 0.0077(4) -0.0010(4)
C25 0.0152(5) 0.0200(5) 0.0196(5) -0.0002(4) 0.0042(4) 0.0002(4)
C26 0.0155(5) 0.0190(5) 0.0220(5) -0.0030(4) 0.0085(4) -0.0017(4)
C27 0.0139(5) 0.0313(6) 0.0379(6) 0.0085(5) 0.0086(5) -0.0009(4)
C28 0.0233(6) 0.0304(6) 0.0223(6) 0.0070(5) 0.0026(5) -0.0028(5)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them
(* indicates atom used to define plane)

- 7.7001 (0.0043) x - 3.0074 (0.0048) y + 11.8816 (0.0082) z = 0.3171 (0.0022)

* -0.0190 (0.0007) C11
* 0.0025 (0.0007) C12
* 0.0173 (0.0007) C13
* -0.0208 (0.0007) C14
* 0.0038 (0.0007) C15
* 0.0162 (0.0007) C16

Rms deviation of fitted atoms = 0.0151

- 6.6648 (0.0045) x - 4.4936 (0.0059) y + 13.5705 (0.0094) z = 0.0182 (0.0039)

Angle to previous plane (with approximate esd) = 13.53 ( 0.06 )

* -0.0142 (0.0003) C11
* 0.0432 (0.0008) C1
* -0.0162 (0.0003) O1
* -0.0127 (0.0002) C2

Rms deviation of fitted atoms = 0.0249

- 0.0044 (0.0045) x + 9.5999 (0.0059) y + 8.9529 (0.0093) z = 7.4103 (0.0040)

Angle to previous plane (with approximate esd) = 85.27 ( 0.05 )

* 0.0101 (0.0002) C1
* -0.0344 (0.0008) C2
* 0.0129 (0.0003) O2
* 0.0114 (0.0003) C21

Rms deviation of fitted atoms = 0.0199

- 1.6204 (0.0035) x + 9.6554 (0.0056) y + 9.5854 (0.0080) z = 7.1370 (0.0042)

Angle to previous plane (with approximate esd) = 11.25 ( 0.06 )

* -0.0112 (0.0007) C21
* 0.0123 (0.0007) C22
* -0.0002 (0.0007) C23
* -0.0129 (0.0007) C24
* 0.0136 (0.0007) C25
* -0.0016 (0.0007) C26

Rms deviation of fitted atoms = 0.0103

- 7.3685 (0.0041) x - 3.4249 (0.0039) y + 12.7600 (0.0071) z = 0.2236 (0.0016)

Angle to previous plane (with approximate esd) = 84.25 ( 0.04 )

;

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
O1 C1 1.2255(12) . ?
O2 C2 1.2268(12) . ?
O3 C12 1.3559(12) . ?
O3 C17 1.4343(12) . ?
O4 C14 1.3634(12) . ?
O4 C18 1.4325(14) . ?
O5 C22 1.3619(13) . ?
O5 C27 1.4291(13) . ?
O6 C24 1.3606(12) . ?
O6 C28 1.4385(14) . ?
C1 C11 1.4689(14) . ?
C1 C2 1.5329(15) . ?
C2 C21 1.4709(14) . ?
C11 C16 1.3984(14) . ?
C11 C12 1.4107(14) . ?
C12 C13 1.3840(14) . ?
C13 C14 1.3938(14) . ?
C14 C15 1.3935(15) . ?
C15 C16 1.3804(15) . ?
C21 C26 1.3932(15) . ?
C21 C22 1.4140(13) . ?
C22 C23 1.3817(14) . ?
C23 C24 1.3980(15) . ?
C24 C25 1.3953(14) . ?
C25 C26 1.3809(14) . ?

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
C12 O3 C17 118.37(8) . . ?
C14 O4 C18 117.42(9) . . ?
C22 O5 C27 118.73(8) . . ?
C24 O6 C28 118.05(8) . . ?
O1 C1 C11 122.70(9) . . ?
O1 C1 C2 115.60(9) . . ?
C11 C1 C2 121.18(9) . . ?
O2 C2 C21 123.17(10) . . ?
O2 C2 C1 115.28(9) . . ?
C21 C2 C1 121.23(9) . . ?
C16 C11 C12 118.13(9) . . ?
C16 C11 C1 118.55(9) . . ?
C12 C11 C1 123.29(9) . . ?
O3 C12 C13 123.79(9) . . ?
O3 C12 C11 115.88(9) . . ?
C13 C12 C11 120.33(9) . . ?
C12 C13 C14 119.64(9) . . ?
O4 C14 C15 124.37(9) . . ?
O4 C14 C13 114.32(9) . . ?
C15 C14 C13 121.30(9) . . ?
C16 C15 C14 118.15(9) . . ?
C15 C16 C11 122.31(10) . . ?
C26 C21 C22 118.11(9) . . ?
C26 C21 C2 119.20(9) . . ?
C22 C21 C2 122.65(9) . . ?
O5 C22 C23 123.64(9) . . ?
O5 C22 C21 116.00(9) . . ?
C23 C22 C21 120.36(9) . . ?
C22 C23 C24 119.73(9) . . ?
O6 C24 C25 124.26(9) . . ?
O6 C24 C23 114.71(9) . . ?
C25 C24 C23 121.02(9) . . ?
C26 C25 C24 118.22(10) . . ?
C25 C26 C21 122.49(10) . . ?

_diffrn_measured_fraction_theta_max 0.951
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.044