#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/23/4112370.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_4112370
loop_
_publ_author_name
'Dario Braga'
'Shuang Chen'
'Heather Filson'
'Lucia Maini'
'Matthew R. Netherton'
'Brian O. Patrick'
'John R. Scheffer'
'Carl Scott'
'Wujiong Xia'
_publ_contact_author_address
;
   Department of Chemistry
   The University of British Columbia
   2036 Main Mall
   Vancouver, BC V6T 1Z1
;
_publ_contact_author_email       ' scheffer@chem.ubc.ca '
_publ_contact_author_fax         ' 604-822-2847 '
_publ_contact_author_name        ' Dr John R. Scheffer'
_publ_contact_author_phone       ' 604-822-3496 '
_publ_section_title
;
 1,4-Hydroxybiradical Behavior Revealed through Crystal
 Structure-Solid-State Reactivity Correlations
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3511
_journal_page_last               3520
_journal_paper_doi               10.1021/ja039076w
_journal_volume                  126
_journal_year                    2004
_chemical_formula_moiety         'C20 H24 O3 '
_chemical_formula_sum            'C20 H24 O3'
_chemical_formula_weight         312.41
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_date             2003-09-23
_audit_creation_method           'by teXsan v1.8'
_cell_angle_alpha                90
_cell_angle_beta                 97.789(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3399(8)
_cell_length_b                   6.5515(8)
_cell_length_c                   22.473(1)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294.2
_cell_measurement_theta_max      47.3
_cell_measurement_theta_min      42.9
_cell_volume                     1654.2(2)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        'teXsan (MSC, 1992-1997)'
_computing_publication_material  'teXsan (MSC, 1992-1997)'
_computing_structure_refinement  'teXsan (MSC, 1992-1997)'
_computing_structure_solution
;
SIR92 (Altomare, et. al. 1993)
;
_diffrn_ambient_temperature      294.2
_diffrn_measurement_device_type  'Rigaku AFC6S'
_diffrn_measurement_method       ω-2θ
_diffrn_orient_matrix_UB_11      0.03616
_diffrn_orient_matrix_UB_12      -0.13706
_diffrn_orient_matrix_UB_13      -0.00506
_diffrn_orient_matrix_UB_21      0.07830
_diffrn_orient_matrix_UB_22      0.06631
_diffrn_orient_matrix_UB_23      -0.00324
_diffrn_orient_matrix_UB_31      0.02199
_diffrn_orient_matrix_UB_32      -0.01075
_diffrn_orient_matrix_UB_33      0.04451
_diffrn_radiation_detector       'scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.01333
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            3861
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         77.50
_diffrn_reflns_theta_min         1.99
_diffrn_standards_decay_%        -1.60
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.660
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.876
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
(North,Phillips & Matthews, 1968)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_description       prism
_exptl_crystal_F_000             672.00
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.19
_refine_ls_extinction_coef       0.0000084(6)
_refine_ls_extinction_expression 'equ(3) Acta Cryst.(1968) A24, p213.'
_refine_ls_extinction_method     'Zachariasen (1967)'
_refine_ls_goodness_of_fit_all   1.916
_refine_ls_goodness_of_fit_ref   1.916
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3367
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0403
_refine_ls_shift/su_max          0.0004
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 1/[σ²(Fo²) + 0.00022|Fo|²]'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         0.1262
_refine_ls_wR_factor_ref         0.1262
_reflns_number_gt                2294
_reflns_number_total             3678
_reflns_threshold_expression     I>3.00σ(I)
_cod_data_source_file            ja039076wsi20031015_043604_16.cif
_cod_data_source_block           13e
_cod_original_sg_symbol_H-M      'P 21/n '
_cod_original_formula_sum        'C20 H24 O3 '
_cod_database_code               4112370
loop_
_symmetry_equiv_pos_as_xyz
'   +x,   +y,   +z'
1/2-x,1/2+y,1/2-z
'   -x,   -y,   -z'
1/2+x,1/2-y,1/2+z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_refinement_flags
_atom_site_adp_type
_atom_site_calc_flag
O(1) 0.7261(1) -0.3851(2) 0.39708(7) 0.0805(5) 1.000 . Uani d
O(2) 1.2534(1) 0.1400(2) 0.43179(7) 0.0865(5) 1.000 . Uani d
O(3) 1.1559(1) 0.4262(2) 0.44595(6) 0.0680(4) 1.000 . Uani d
C(1) 0.5099(1) -0.2791(2) 0.33636(7) 0.0521(5) 1.000 . Uani d
C(2) 0.5884(1) -0.1145(2) 0.37174(7) 0.0452(4) 1.000 . Uani d
C(3) 0.5818(1) 0.0787(2) 0.33192(8) 0.0509(4) 1.000 . Uani d
C(4) 0.4520(2) 0.1510(3) 0.31734(9) 0.0628(5) 1.000 . Uani d
C(5) 0.3767(2) -0.0147(3) 0.28327(8) 0.0664(6) 1.000 . Uani d
C(6) 0.4244(2) -0.0595(4) 0.22469(9) 0.0842(7) 1.000 . Uani d
C(7) 0.5529(2) -0.1324(3) 0.23868(8) 0.0741(6) 1.000 . Uani d
C(8) 0.6292(2) 0.0314(3) 0.27313(8) 0.0630(5) 1.000 . Uani d
C(9) 0.3815(2) -0.2053(3) 0.32192(8) 0.0610(5) 1.000 . Uani d
C(10) 0.5567(2) -0.3254(3) 0.27674(9) 0.0695(6) 1.000 . Uani d
C(11) 0.5456(1) -0.0728(3) 0.43332(7) 0.0620(5) 1.000 . Uani d
C(12) 0.7135(1) -0.2030(3) 0.38918(7) 0.0527(5) 1.000 . Uani d
C(13) 0.8247(1) -0.0742(3) 0.39967(7) 0.0504(4) 1.000 . Uani d
C(14) 0.9294(1) -0.1668(3) 0.38691(8) 0.0587(5) 1.000 . Uani d
C(15) 1.0357(1) -0.0656(3) 0.39742(8) 0.0607(5) 1.000 . Uani d
C(16) 1.0427(1) 0.1297(3) 0.42171(7) 0.0536(5) 1.000 . Uani d
C(17) 0.9391(1) 0.2232(3) 0.43454(8) 0.0571(5) 1.000 . Uani d
C(18) 0.8313(1) 0.1218(3) 0.42285(8) 0.0576(5) 1.000 . Uani d
C(19) 1.1617(1) 0.2288(3) 0.43359(7) 0.0588(5) 1.000 . Uani d
C(20) 1.2685(2) 0.5314(3) 0.4568(1) 0.0767(7) 1.000 . Uani d
H(1) 0.5121 -0.4054 0.3607 0.063 1.000 . Uiso c
H(2) 0.6304 0.1884 0.3535 0.060 1.000 . Uiso c
H(3) 0.4493 0.2755 0.2922 0.076 1.000 . Uiso c
H(4) 0.4198 0.1822 0.3551 0.076 1.000 . Uiso c
H(5) 0.2930 0.0325 0.2745 0.079 1.000 . Uiso c
H(6) 0.3757 -0.1678 0.2025 0.100 1.000 . Uiso c
H(7) 0.4213 0.0654 0.2000 0.100 1.000 . Uiso c
H(8) 0.5846 -0.1629 0.2006 0.088 1.000 . Uiso c
H(9) 0.6271 0.1566 0.2482 0.075 1.000 . Uiso c
H(10) 0.7126 -0.0179 0.2816 0.075 1.000 . Uiso c
H(11) 0.3491 -0.1746 0.3597 0.074 1.000 . Uiso c
H(12) 0.3327 -0.3143 0.2998 0.074 1.000 . Uiso c
H(13) 0.5059 -0.4315 0.2545 0.084 1.000 . Uiso c
H(14) 0.6395 -0.3759 0.2848 0.084 1.000 . Uiso c
H(15a) 0.5998 0.0264 0.4564 0.075 0.79(2) PPPPP Uiso d
H(15b) 0.5218 0.0721 0.4356 0.075 0.206 P Uiso d
H(16a) 0.4640 -0.0161 0.4269 0.075 0.794 P Uiso d
H(16b) 0.4767 -0.1615 0.4379 0.075 0.206 P Uiso d
H(17a) 0.5458 -0.2020 0.4562 0.075 0.794 P Uiso d
H(17b) 0.6111 -0.1024 0.4661 0.075 0.206 P Uiso d
H(18) 0.9267 -0.3067 0.3704 0.069 1.000 . Uiso c
H(19) 1.1088 -0.1323 0.3872 0.073 1.000 . Uiso c
H(20) 0.9423 0.3622 0.4519 0.068 1.000 . Uiso c
H(21) 0.7575 0.1907 0.4312 0.068 1.000 . Uiso c
H(22a) 1.3163 0.4975 0.4241 0.093 0.86(2) PPPPP Uiso d
H(22b) 1.3336 0.4305 0.4645 0.093 0.143 P Uiso d
H(23a) 1.3119 0.4884 0.4957 0.093 0.857 P Uiso d
H(23b) 1.2692 0.6228 0.4916 0.093 0.143 P Uiso d
H(24b) 1.2796 0.6130 0.4206 0.093 0.143 P Uiso d
H(24a) 1.2543 0.6804 0.4569 0.093 0.857 P Uiso d
loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_number_in_cell
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0 80 0.017 0.009
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H 0 96 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
O 0 12 0.047 0.032
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O(1) C(20) 3.416(3) 3_756 no
O(1) C(18) 3.463(3) 1_545 no
O(1) C(17) 3.544(2) 1_545 no
O(2) C(11) 3.564(3) 3_756 no
O(2) C(11) 3.589(2) 1_655 no
C(11) C(11) 3.432(4) 3_656 no
O(1) H(23a) 2.5914 3_756 no
O(1) H(21) 2.8897 1_545 no
O(1) H(23b) 2.9378 3_756 no
O(2) H(17b) 2.5969 3_756 no
O(2) H(16a) 2.6122 1_655 no
O(2) H(4) 2.7349 1_655 no
O(2) H(11) 2.9183 1_655 no
O(2) H(15a) 3.025(2) 3_756 no
O(3) H(20) 3.0216 3_766 no
C(9) H(24b) 2.8914 1_445 no
C(10) H(3) 2.9233 1_545 no
C(18) H(23b) 2.8956 3_766 no
H(1) H(3) 2.6375 1_545 no
H(3) H(13) 2.2271 1_565 no
H(5) H(12) 2.2765 2 no
H(7) H(18) 2.6288 2_655 no
H(9) H(18) 2.6625 2_655 no
H(10) H(14) 2.5647 2_655 no
H(11) H(24b) 2.1747 1_445 no
H(11) H(22a) 2.6461 1_445 no
H(16b) H(24b) 2.6633 1_445 no
H(17a) H(23a) 2.6113 3_756 no
H(17b) H(22b) 2.6797 3_756 no
H(19) H(24a) 2.4461 1_545 no
H(19) H(24b) 2.5901 1_545 no
H(21) H(23b) 2.1767 3_766 no
H(21) H(24a) 2.6736 3_766 no
