#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:26:53 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180299 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/13/7151346.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_7151346
loop_
_publ_author_name
'Alonso, A. Mateo'
'Horcajada, Roberto'
'Motevalli, Majid'
'Utley, James H. P.'
'Wyatt, Peter B.'
_publ_section_title
;
 The reactivity, as electrogenerated bases, of chiral and achiral
 phenazine radical-anions, including application in asymmetric
 deprotonation.
;
_journal_issue                   15
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2842
_journal_page_last               2847
_journal_paper_doi               10.1039/b506309d
_journal_volume                  3
_journal_year                    2005
_chemical_formula_sum            'C14 H16 O4 S'
_chemical_formula_weight         280.33
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.57(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.102(8)
_cell_length_b                   10.963(6)
_cell_length_c                   5.929(2)
_cell_measurement_temperature    160(2)
_cell_volume                     1370.2(10)
_computing_cell_refinement       'CAD4 /PC (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 /PC (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      160(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled omega/2theta scans'
_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  0.0192
_diffrn_reflns_av_sigmaI/netI    0.0933
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2730
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.09
_diffrn_standards_decay_%        2
_diffrn_standards_interval_count 100
_diffrn_standards_interval_time  60
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_T_max  0.9879
_exptl_absorpt_correction_T_min  0.9090
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
Number of psi-scan sets used was 3
Theta correction was applied.
Averaged transmission function was used.
No Fourier smoothing was applied.

;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       plate
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2394
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.1293
_refine_ls_R_factor_gt           0.0521
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0794P)²+0.2457P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1250
_refine_ls_wR_factor_ref         0.1498
_reflns_number_gt                1400
_reflns_number_total             2394
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b506309d.txt
_cod_data_source_block           ama-157
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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      P21/c
_cod_database_code               7151346
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'
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
S1 S 0.43681(4) 0.93814(9) 0.26749(17) 0.0271(3) Uani 1 1 d . . .
O1 O 0.50423(13) 0.9202(3) 0.2624(5) 0.0391(7) Uani 1 1 d . . .
O2 O 0.40441(13) 0.8794(3) 0.4452(5) 0.0390(8) Uani 1 1 d . . .
O3 O 0.29849(11) 0.9907(2) -0.1043(4) 0.0298(7) Uani 1 1 d . . .
O4 O 0.28531(13) 1.1333(3) -0.3739(6) 0.0453(8) Uani 1 1 d . . .
C1 C 0.41654(18) 1.0921(3) 0.2621(7) 0.0272(9) Uani 1 1 d . . .
H1 H 0.4310 1.1499 0.3722 0.033 Uiso 1 1 calc R . .
C2 C 0.37854(18) 1.1185(4) 0.0853(7) 0.0300(9) Uani 1 1 d . . .
H2 H 0.3599 1.1970 0.0670 0.036 Uiso 1 1 calc R . .
C3 C 0.36619(17) 1.0201(3) -0.0833(7) 0.0277(9) Uani 1 1 d . . .
H3 H 0.3818 1.0452 -0.2332 0.033 Uiso 1 1 calc R . .
C4 C 0.40027(18) 0.9041(3) -0.0014(7) 0.0315(10) Uani 1 1 d . . .
H4A H 0.4326 0.8798 -0.1086 0.038 Uiso 1 1 calc R . .
H4B H 0.3696 0.8364 0.0112 0.038 Uiso 1 1 calc R . .
C5 C 0.26414(17) 1.0531(4) -0.2632(7) 0.0283(9) Uani 1 1 d . . .
C6 C 0.19812(17) 1.0033(4) -0.2859(6) 0.0272(9) Uani 1 1 d . . .
C7 C 0.15230(18) 1.0435(4) -0.1432(7) 0.0317(10) Uani 1 1 d . . .
C8 C 0.09170(18) 0.9937(4) -0.1700(7) 0.0394(11) Uani 1 1 d . . .
H8 H 0.0599 1.0202 -0.0728 0.047 Uiso 1 1 calc R . .
C9 C 0.07627(19) 0.9078(4) -0.3316(7) 0.0388(11) Uani 1 1 d . . .
C10 C 0.12325(19) 0.8691(4) -0.4711(7) 0.0380(11) Uani 1 1 d . . .
H10 H 0.1131 0.8095 -0.5834 0.046 Uiso 1 1 calc R . .
C11 C 0.18487(19) 0.9148(4) -0.4517(7) 0.0333(10) Uani 1 1 d . . .
C12 C 0.1667(2) 1.1388(4) 0.0372(8) 0.0462(12) Uani 1 1 d . . .
H12A H 0.1774 1.0982 0.1812 0.069 Uiso 1 1 calc R . .
H12B H 0.1294 1.1908 0.0533 0.069 Uiso 1 1 calc R . .
H12C H 0.2026 1.1888 -0.0065 0.069 Uiso 1 1 calc R . .
C13 C 0.0105(2) 0.8541(5) -0.3593(9) 0.0602(15) Uani 1 1 d . . .
H13A H -0.0093 0.8806 -0.5037 0.090 Uiso 1 1 calc R . .
H13B H -0.0152 0.8819 -0.2356 0.090 Uiso 1 1 calc R . .
H13C H 0.0133 0.7648 -0.3566 0.090 Uiso 1 1 calc R . .
C14 C 0.2349(2) 0.8687(4) -0.6007(8) 0.0452(12) Uani 1 1 d . . .
H14A H 0.2227 0.7880 -0.6593 0.068 Uiso 1 1 calc R . .
H14B H 0.2753 0.8625 -0.5137 0.068 Uiso 1 1 calc R . .
H14C H 0.2394 0.9252 -0.7270 0.068 Uiso 1 1 calc R . .
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'
S S 0.1246 0.1234 '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
O2 S1 O1 117.28(18) . . ?
O2 S1 C1 108.92(18) . . ?
O1 S1 C1 112.00(18) . . ?
O2 S1 C4 111.25(18) . . ?
O1 S1 C4 110.01(19) . . ?
C1 S1 C4 95.20(19) . . ?
C5 O3 C3 116.1(3) . . ?
C2 C1 S1 111.5(3) . . ?
C2 C1 H1 124.3 . . ?
S1 C1 H1 124.3 . . ?
C1 C2 C3 117.1(4) . . ?
C1 C2 H2 121.4 . . ?
C3 C2 H2 121.4 . . ?
O3 C3 C2 111.0(3) . . ?
O3 C3 C4 106.7(3) . . ?
C2 C3 C4 108.9(3) . . ?
O3 C3 H3 110.1 . . ?
C2 C3 H3 110.1 . . ?
C4 C3 H3 110.1 . . ?
C3 C4 S1 106.8(3) . . ?
C3 C4 H4A 110.4 . . ?
S1 C4 H4A 110.4 . . ?
C3 C4 H4B 110.4 . . ?
S1 C4 H4B 110.4 . . ?
H4A C4 H4B 108.6 . . ?
O4 C5 O3 123.6(3) . . ?
O4 C5 C6 126.0(4) . . ?
O3 C5 C6 110.3(3) . . ?
C7 C6 C11 121.8(4) . . ?
C7 C6 C5 120.1(4) . . ?
C11 C6 C5 118.1(3) . . ?
C6 C7 C8 117.9(4) . . ?
C6 C7 C12 121.8(4) . . ?
C8 C7 C12 120.3(4) . . ?
C9 C8 C7 122.4(4) . . ?
C9 C8 H8 118.8 . . ?
C7 C8 H8 118.8 . . ?
C8 C9 C10 118.2(4) . . ?
C8 C9 C13 122.1(4) . . ?
C10 C9 C13 119.6(4) . . ?
C9 C10 C11 122.0(4) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
C10 C11 C6 117.6(4) . . ?
C10 C11 C14 120.7(4) . . ?
C6 C11 C14 121.7(4) . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
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
S1 O2 1.434(3) . ?
S1 O1 1.438(3) . ?
S1 C1 1.742(4) . ?
S1 C4 1.779(4) . ?
O3 C5 1.349(4) . ?
O3 C3 1.464(4) . ?
O4 C5 1.196(5) . ?
C1 C2 1.323(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.486(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.529(5) . ?
C3 H3 1.0000 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.497(5) . ?
C6 C7 1.385(5) . ?
C6 C11 1.400(6) . ?
C7 C8 1.393(5) . ?
C7 C12 1.516(6) . ?
C8 C9 1.373(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.386(6) . ?
C9 C13 1.510(6) . ?
C10 C11 1.394(6) . ?
C10 H10 0.9500 . ?
C11 C14 1.495(6) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
