#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/54/4025477.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_4025477
loop_
_publ_author_name
'Saurav J. Sarma'
'Paul B. Jones'
_publ_section_title
;
 Photochemistry of 1,n-Dibenzyloxy-9,10-anthraquinones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3806
_journal_page_last               3813
_journal_paper_doi               10.1021/jo100650u
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C21 H14 O4'
_chemical_formula_sum            'C21 H14 O4'
_chemical_formula_weight         330.32
_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           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 110.458(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.014(3)
_cell_length_b                   8.101(2)
_cell_length_c                   16.536(4)
_cell_measurement_reflns_used    2201
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      29.636
_cell_measurement_theta_min      4.224
_cell_volume                     1507.9(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0342
_diffrn_reflns_av_sigmaI/netI    0.0336
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13564
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         4.22
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.8622
_exptl_absorpt_correction_T_min  0.7603
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 Data were corrected for scaling and absorption using the 
 multi-scan technique (SADABS).  
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3444
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0938
_refine_ls_R_factor_gt           0.0613
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0846P)²+0.3183P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1512
_refine_ls_wR_factor_ref         0.1709
_reflns_number_gt                2260
_reflns_number_total             3444
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100650u_si_003.cif
_cod_data_source_block           a91o_22
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        1507.8(7)
_cod_database_code               4025477
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
O1 O -0.09078(13) 0.6477(2) -0.09072(9) 0.0522(4) Uani 1 1 d . . .
O2 O -0.38177(14) 0.4035(2) 0.06359(11) 0.0614(5) Uani 1 1 d . . .
O3 O 0.04183(12) 0.77701(18) 0.05237(8) 0.0477(4) Uani 1 1 d . . .
O4 O -0.25942(16) 0.5265(3) 0.20735(11) 0.0706(5) Uani 1 1 d . . .
H41 H -0.315(3) 0.455(4) 0.158(2) 0.115(12) Uiso 1 1 d . . .
C1 C -0.15360(17) 0.5961(2) -0.05320(13) 0.0400(4) Uani 1 1 d . . .
C2 C -0.12947(17) 0.6222(2) 0.04041(12) 0.0391(4) Uani 1 1 d . . .
C3 C -0.03235(17) 0.7162(2) 0.09085(12) 0.0412(5) Uani 1 1 d . . .
C4 C -0.0146(2) 0.7439(3) 0.17823(13) 0.0504(5) Uani 1 1 d . . .
H4 H 0.0514 0.8080 0.2122 0.061 Uiso 1 1 calc R . .
C5 C -0.0907(2) 0.6800(3) 0.21530(14) 0.0556(6) Uani 1 1 d . . .
H5 H -0.0774 0.7010 0.2745 0.067 Uiso 1 1 calc R . .
C6 C -0.1867(2) 0.5850(3) 0.16739(14) 0.0507(5) Uani 1 1 d . . .
C7 C -0.20760(17) 0.5556(2) 0.07962(13) 0.0433(5) Uani 1 1 d . . .
C8 C -0.31357(18) 0.4610(2) 0.02920(14) 0.0457(5) Uani 1 1 d . . .
C9 C -0.33888(17) 0.4363(2) -0.06375(14) 0.0451(5) Uani 1 1 d . . .
C10 C -0.43861(19) 0.3459(3) -0.11222(16) 0.0560(6) Uani 1 1 d . . .
H10 H -0.4904 0.3020 -0.0855 0.067 Uiso 1 1 calc R . .
C11 C -0.4619(2) 0.3203(3) -0.19876(17) 0.0630(7) Uani 1 1 d . . .
H11 H -0.5295 0.2579 -0.2316 0.076 Uiso 1 1 calc R . .
C12 C -0.3875(2) 0.3848(3) -0.23828(16) 0.0595(6) Uani 1 1 d . . .
H12 H -0.4043 0.3665 -0.2981 0.071 Uiso 1 1 calc R . .
C13 C -0.28842(19) 0.4763(3) -0.19096(14) 0.0507(5) Uani 1 1 d . . .
H13 H -0.2377 0.5215 -0.2183 0.061 Uiso 1 1 calc R . .
C14 C -0.26383(16) 0.5013(2) -0.10296(13) 0.0410(5) Uani 1 1 d . . .
C15 C 0.13026(18) 0.8941(3) 0.09795(13) 0.0468(5) Uani 1 1 d . . .
H15A H 0.1851 0.8444 0.1519 0.056 Uiso 1 1 calc R . .
H15B H 0.0924 0.9920 0.1132 0.056 Uiso 1 1 calc R . .
C16 C 0.19713(16) 0.9436(2) 0.04090(13) 0.0404(5) Uani 1 1 d . . .
C17 C 0.16335(18) 0.8933(2) -0.04417(13) 0.0453(5) Uani 1 1 d . . .
H17 H 0.0959 0.8243 -0.0681 0.054 Uiso 1 1 calc R . .
C18 C 0.2280(2) 0.9439(3) -0.09431(15) 0.0536(6) Uani 1 1 d . . .
H18 H 0.2043 0.9093 -0.1528 0.064 Uiso 1 1 calc R . .
C19 C 0.3261(2) 1.0434(3) -0.06081(17) 0.0569(6) Uani 1 1 d . . .
H19 H 0.3698 1.0773 -0.0960 0.068 Uiso 1 1 calc R . .
C20 C 0.36094(19) 1.0941(3) 0.02423(17) 0.0562(6) Uani 1 1 d . . .
H20 H 0.4287 1.1628 0.0477 0.067 Uiso 1 1 calc R . .
C21 C 0.29678(18) 1.0443(3) 0.07514(15) 0.0517(6) Uani 1 1 d . . .
H21 H 0.3208 1.0789 0.1336 0.062 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'
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
C3 O3 C15 118.93(16) . . ?
C6 O4 H41 99.4(19) . . ?
O1 C1 C2 123.80(18) . . ?
O1 C1 C14 119.04(18) . . ?
C2 C1 C14 117.15(17) . . ?
C3 C2 C7 118.75(18) . . ?
C3 C2 C1 121.10(18) . . ?
C7 C2 C1 120.12(18) . . ?
O3 C3 C2 117.78(17) . . ?
O3 C3 C4 122.49(19) . . ?
C2 C3 C4 119.72(19) . . ?
C5 C4 C3 121.1(2) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 120.5(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
O4 C6 C5 117.8(2) . . ?
O4 C6 C7 122.2(2) . . ?
C5 C6 C7 119.9(2) . . ?
C6 C7 C2 119.96(19) . . ?
C6 C7 C8 118.77(19) . . ?
C2 C7 C8 121.23(18) . . ?
O2 C8 C7 121.1(2) . . ?
O2 C8 C9 119.96(19) . . ?
C7 C8 C9 118.98(18) . . ?
C14 C9 C10 120.0(2) . . ?
C14 C9 C8 120.42(18) . . ?
C10 C9 C8 119.6(2) . . ?
C11 C10 C9 119.9(2) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 120.4(2) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C13 120.3(2) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C14 119.5(2) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C9 C14 C13 119.87(19) . . ?
C9 C14 C1 122.08(18) . . ?
C13 C14 C1 118.04(18) . . ?
O3 C15 C16 108.10(16) . . ?
O3 C15 H15A 110.1 . . ?
C16 C15 H15A 110.1 . . ?
O3 C15 H15B 110.1 . . ?
C16 C15 H15B 110.1 . . ?
H15A C15 H15B 108.4 . . ?
C17 C16 C21 119.4(2) . . ?
C17 C16 C15 122.19(18) . . ?
C21 C16 C15 118.43(19) . . ?
C18 C17 C16 119.8(2) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C19 C18 C17 121.0(2) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C19 C20 119.7(2) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C19 C20 C21 119.8(2) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C20 C21 C16 120.3(2) . . ?
C20 C21 H21 119.8 . . ?
C16 C21 H21 119.8 . . ?
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 1.207(2) . ?
O2 C8 1.240(2) . ?
O3 C3 1.356(2) . ?
O3 C15 1.427(2) . ?
O4 C6 1.352(3) . ?
O4 H41 1.03(4) . ?
C1 C2 1.487(3) . ?
C1 C14 1.503(3) . ?
C2 C3 1.399(3) . ?
C2 C7 1.420(3) . ?
C3 C4 1.403(3) . ?
C4 C5 1.368(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.404(3) . ?
C7 C8 1.470(3) . ?
C8 C9 1.472(3) . ?
C9 C14 1.385(3) . ?
C9 C10 1.394(3) . ?
C10 C11 1.374(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.380(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.395(3) . ?
C13 H13 0.9500 . ?
C15 C16 1.492(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.382(3) . ?
C16 C21 1.395(3) . ?
C17 C18 1.382(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.375(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.382(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.385(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H41 O2 1.03(4) 1.54(4) 2.522(2) 156(3) .
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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 2.6(3) . . . . ?
C14 C1 C2 C3 -176.65(16) . . . . ?
O1 C1 C2 C7 -179.41(18) . . . . ?
C14 C1 C2 C7 1.3(3) . . . . ?
C15 O3 C3 C2 170.24(16) . . . . ?
C15 O3 C3 C4 -10.0(3) . . . . ?
C7 C2 C3 O3 179.28(16) . . . . ?
C1 C2 C3 O3 -2.7(3) . . . . ?
C7 C2 C3 C4 -0.5(3) . . . . ?
C1 C2 C3 C4 177.55(18) . . . . ?
O3 C3 C4 C5 -179.59(19) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C4 C5 C6 O4 -179.4(2) . . . . ?
C4 C5 C6 C7 -1.0(3) . . . . ?
O4 C6 C7 C2 178.96(19) . . . . ?
C5 C6 C7 C2 0.6(3) . . . . ?
O4 C6 C7 C8 1.3(3) . . . . ?
C5 C6 C7 C8 -177.07(19) . . . . ?
C3 C2 C7 C6 0.1(3) . . . . ?
C1 C2 C7 C6 -177.95(17) . . . . ?
C3 C2 C7 C8 177.72(17) . . . . ?
C1 C2 C7 C8 -0.3(3) . . . . ?
C6 C7 C8 O2 -2.1(3) . . . . ?
C2 C7 C8 O2 -179.79(18) . . . . ?
C6 C7 C8 C9 177.23(18) . . . . ?
C2 C7 C8 C9 -0.4(3) . . . . ?
O2 C8 C9 C14 179.44(18) . . . . ?
C7 C8 C9 C14 0.1(3) . . . . ?
O2 C8 C9 C10 -1.1(3) . . . . ?
C7 C8 C9 C10 179.57(18) . . . . ?
C14 C9 C10 C11 0.4(3) . . . . ?
C8 C9 C10 C11 -179.1(2) . . . . ?
C9 C10 C11 C12 -0.5(3) . . . . ?
C10 C11 C12 C13 0.0(4) . . . . ?
C11 C12 C13 C14 0.6(3) . . . . ?
C10 C9 C14 C13 0.1(3) . . . . ?
C8 C9 C14 C13 179.64(18) . . . . ?
C10 C9 C14 C1 -178.46(17) . . . . ?
C8 C9 C14 C1 1.0(3) . . . . ?
C12 C13 C14 C9 -0.7(3) . . . . ?
C12 C13 C14 C1 177.99(18) . . . . ?
O1 C1 C14 C9 178.99(18) . . . . ?
C2 C1 C14 C9 -1.7(3) . . . . ?
O1 C1 C14 C13 0.4(3) . . . . ?
C2 C1 C14 C13 179.64(17) . . . . ?
C3 O3 C15 C16 -178.62(16) . . . . ?
O3 C15 C16 C17 6.9(3) . . . . ?
O3 C15 C16 C21 -173.22(16) . . . . ?
C21 C16 C17 C18 -0.4(3) . . . . ?
C15 C16 C17 C18 179.52(18) . . . . ?
C16 C17 C18 C19 0.2(3) . . . . ?
C17 C18 C19 C20 0.0(3) . . . . ?
C18 C19 C20 C21 0.0(3) . . . . ?
C19 C20 C21 C16 -0.1(3) . . . . ?
C17 C16 C21 C20 0.3(3) . . . . ?
C15 C16 C21 C20 -179.56(18) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659216
