#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/58/1515896.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_1515896
loop_
_publ_author_name
'Pandurangan, Komala'
'Gallagher, Shane'
'Morgan, Grace G.'
'Müller-Bunz, Helge'
'Paradisi, Francesca'
_publ_section_title
;
 Structure and antibacterial activity of the silver(I) complex of
 2-aminophenoxazine-3-one.
;
_journal_issue                   8
_journal_name_full               'Metallomics : integrated biometal science'
_journal_page_first              530
_journal_page_last               534
_journal_paper_doi               10.1039/c003515g
_journal_volume                  2
_journal_year                    2010
_chemical_formula_moiety         '3 (C6 H2 O2 Cl4), 2 (C12 H8 N2 O2)'
_chemical_formula_sum            'C42 H22 Cl12 N4 O10'
_chemical_formula_weight         1168.04
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.180(3)
_cell_angle_beta                 104.737(3)
_cell_angle_gamma                109.772(3)
_cell_formula_units_Z            1
_cell_length_a                   9.3384(13)
_cell_length_b                   10.8469(15)
_cell_length_c                   12.0839(16)
_cell_measurement_reflns_used    3008
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.33
_cell_measurement_theta_min      2.35
_cell_volume                     1072.6(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_sigmaI/netI    0.0374
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9505
_diffrn_reflns_theta_full        26.42
_diffrn_reflns_theta_max         26.42
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    0.842
_exptl_absorpt_correction_T_max  0.9591
_exptl_absorpt_correction_T_min  0.7580
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS v.2.10 (Bruker,2003) was used for absorption correction.
R(int) for selected reflections was 0.053 before and 0.020 after
correction. The Ratio of minimum to maximum transmission is 0.790333.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.808
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             586
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.573
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         4381
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0384
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0516P)²+0.4625P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0944
_reflns_number_gt                3579
_reflns_number_total             4381
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c003515g.txt
_cod_data_source_block           mor300
_cod_original_formula_sum        'C42 H22 N4 O10 Cl12'
_cod_database_code               1515896
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
O1 O 0.6354(2) 0.37630(18) 0.47329(15) 0.0214(4) Uani 1 1 d .
C1 C 0.6787(3) 0.4945(3) 0.4411(2) 0.0168(5) Uani 1 1 d .
C2 C 0.5660(3) 0.5075(3) 0.3382(2) 0.0141(5) Uani 1 1 d .
C3 C 0.6141(3) 0.6315(3) 0.3065(2) 0.0161(5) Uani 1 1 d .
H3 H 0.5445 0.6417 0.2393 0.019 Uiso 1 1 calc R
C4 C 0.7580(3) 0.7366(3) 0.3700(2) 0.0164(5) Uani 1 1 d .
N1 N 0.8112(3) 0.8567(2) 0.3465(2) 0.0221(5) Uani 1 1 d D
H1N1 H 0.906(3) 0.923(2) 0.397(2) 0.033 Uiso 1 1 d D
H2N1 H 0.742(3) 0.881(3) 0.297(2) 0.033 Uiso 1 1 d D
C5 C 0.8725(3) 0.7209(3) 0.4734(2) 0.0187(6) Uani 1 1 d .
O2 O 1.0043(2) 0.8164(2) 0.52940(16) 0.0267(4) Uani 1 1 d .
C6 C 0.8232(3) 0.5946(3) 0.5030(2) 0.0212(6) Uani 1 1 d .
H6 H 0.8937 0.5812 0.5675 0.025 Uiso 1 1 calc R
N2 N 0.4250(2) 0.4082(2) 0.27880(17) 0.0140(4) Uani 1 1 d .
C7 C 0.4855(3) 0.2745(3) 0.4137(2) 0.0182(5) Uani 1 1 d .
C8 C 0.3811(3) 0.2906(3) 0.3170(2) 0.0150(5) Uani 1 1 d .
C9 C 0.2294(3) 0.1856(3) 0.2595(2) 0.0190(5) Uani 1 1 d .
H9 H 0.1564 0.1939 0.1930 0.023 Uiso 1 1 calc R
C10 C 0.1842(3) 0.0695(3) 0.2984(2) 0.0221(6) Uani 1 1 d .
H10 H 0.0804 -0.0015 0.2588 0.027 Uiso 1 1 calc R
C11 C 0.2912(3) 0.0567(3) 0.3957(2) 0.0237(6) Uani 1 1 d .
H11 H 0.2598 -0.0232 0.4221 0.028 Uiso 1 1 calc R
C12 C 0.4410(3) 0.1582(3) 0.4533(2) 0.0232(6) Uani 1 1 d .
H12 H 0.5136 0.1494 0.5195 0.028 Uiso 1 1 calc R
C13 C 0.0237(3) 0.4123(2) -0.0822(2) 0.0115(5) Uani 1 1 d .
Cl1 Cl 0.05549(7) 0.30443(6) -0.18538(5) 0.01591(15) Uani 1 1 d .
C14 C 0.1138(3) 0.4429(2) 0.0372(2) 0.0117(5) Uani 1 1 d .
O3 O 0.2191(2) 0.38367(18) 0.06522(14) 0.0146(4) Uani 1 1 d D
H1O3 H 0.274(3) 0.408(3) 0.1339(16) 0.022 Uiso 1 1 d D
C15 C 0.0876(3) 0.5317(2) 0.1181(2) 0.0113(5) Uani 1 1 d .
Cl2 Cl 0.19651(7) 0.57175(6) 0.26728(5) 0.01393(14) Uani 1 1 d .
C16 C 0.6276(3) 0.8654(2) 0.9730(2) 0.0141(5) Uani 1 1 d .
O4 O 0.7413(2) 0.85430(19) 1.06244(16) 0.0204(4) Uani 1 1 d D
H1O4 H 0.734(4) 0.777(2) 1.044(3) 0.031 Uiso 1 1 d D
C17 C 0.4751(3) 0.7634(2) 0.9164(2) 0.0143(5) Uani 1 1 d .
Cl3 Cl 0.42741(7) 0.61488(6) 0.95959(5) 0.01693(15) Uani 1 1 d .
C18 C 0.3626(3) 0.7797(2) 0.8255(2) 0.0137(5) Uani 1 1 d .
Cl4 Cl 0.17400(7) 0.65117(6) 0.75384(5) 0.01823(15) Uani 1 1 d .
C19 C 0.3996(3) 0.8988(2) 0.7901(2) 0.0148(5) Uani 1 1 d .
O5 O 0.2973(2) 0.92215(19) 0.70236(16) 0.0209(4) Uani 1 1 d D
H1O5 H 0.213(3) 0.857(3) 0.666(3) 0.050(11) Uiso 1 1 d D
C20 C 0.5526(3) 1.0019(2) 0.8480(2) 0.0147(5) Uani 1 1 d .
Cl5 Cl 0.59977(7) 1.14961(6) 0.80328(5) 0.01923(15) Uani 1 1 d .
C21 C 0.6651(3) 0.9854(2) 0.9381(2) 0.0154(5) Uani 1 1 d .
Cl6 Cl 0.85541(7) 1.11200(6) 1.00590(5) 0.02071(16) Uani 1 1 d .
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'
N N 0.0061 0.0033 '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'
Cl Cl 0.1484 0.1585 '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
C1 O1 C7 119.85(19) .
C6 C1 O1 119.0(2) .
C6 C1 C2 122.2(2) .
O1 C1 C2 118.8(2) .
N2 C2 C3 121.2(2) .
N2 C2 C1 121.2(2) .
C3 C2 C1 117.6(2) .
C4 C3 C2 121.5(2) .
C4 C3 H3 119.3 .
C2 C3 H3 119.3 .
N1 C4 C3 125.1(2) .
N1 C4 C5 114.8(2) .
C3 C4 C5 120.1(2) .
C4 N1 H1N1 118.8(19) .
C4 N1 H2N1 120(2) .
H1N1 N1 H2N1 119(3) .
O2 C5 C6 122.8(2) .
O2 C5 C4 119.6(2) .
C6 C5 C4 117.6(2) .
C1 C6 C5 120.9(2) .
C1 C6 H6 119.5 .
C5 C6 H6 119.5 .
C2 N2 C8 118.7(2) .
O1 C7 C12 118.5(2) .
O1 C7 C8 119.8(2) .
C12 C7 C8 121.7(2) .
N2 C8 C9 120.3(2) .
N2 C8 C7 121.6(2) .
C9 C8 C7 118.1(2) .
C10 C9 C8 120.5(2) .
C10 C9 H9 119.7 .
C8 C9 H9 119.7 .
C9 C10 C11 120.0(3) .
C9 C10 H10 120.0 .
C11 C10 H10 120.0 .
C12 C11 C10 120.5(2) .
C12 C11 H11 119.8 .
C10 C11 H11 119.8 .
C11 C12 C7 119.2(2) .
C11 C12 H12 120.4 .
C7 C12 H12 120.4 .
C15 C13 C14 121.1(2) 2_565
C15 C13 Cl1 120.42(18) 2_565
C14 C13 Cl1 118.50(18) .
O3 C14 C15 125.1(2) .
O3 C14 C13 117.6(2) .
C15 C14 C13 117.3(2) .
C14 O3 H1O3 115(2) .
C13 C15 C14 121.7(2) 2_565
C13 C15 Cl2 119.67(19) 2_565
C14 C15 Cl2 118.67(18) .
O4 C16 C17 122.9(2) .
O4 C16 C21 118.6(2) .
C17 C16 C21 118.4(2) .
C16 O4 H1O4 106(2) .
C16 C17 C18 120.8(2) .
C16 C17 Cl3 118.70(18) .
C18 C17 Cl3 120.52(19) .
C19 C18 C17 121.0(2) .
C19 C18 Cl4 118.48(18) .
C17 C18 Cl4 120.51(19) .
O5 C19 C18 124.5(2) .
O5 C19 C20 117.4(2) .
C18 C19 C20 118.1(2) .
C19 O5 H1O5 114(3) .
C21 C20 C19 121.0(2) .
C21 C20 Cl5 120.79(19) .
C19 C20 Cl5 118.22(18) .
C20 C21 C16 120.7(2) .
C20 C21 Cl6 120.34(19) .
C16 C21 Cl6 118.92(18) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.359(3) .
O1 C7 1.373(3) .
C1 C6 1.339(4) .
C1 C2 1.471(3) .
C2 N2 1.312(3) .
C2 C3 1.415(3) .
C3 C4 1.362(3) .
C3 H3 0.9500 .
C4 N1 1.333(3) .
C4 C5 1.499(3) .
N1 H1N1 0.911(18) .
N1 H2N1 0.901(17) .
C5 O2 1.239(3) .
C5 C6 1.424(4) .
C6 H6 0.9500 .
N2 C8 1.392(3) .
C7 C12 1.390(4) .
C7 C8 1.395(3) .
C8 C9 1.393(3) .
C9 C10 1.384(4) .
C9 H9 0.9500 .
C10 C11 1.396(4) .
C10 H10 0.9500 .
C11 C12 1.368(4) .
C11 H11 0.9500 .
C12 H12 0.9500 .
C13 C15 1.386(3) 2_565
C13 C14 1.393(3) .
C13 Cl1 1.723(2) .
C14 O3 1.350(3) .
C14 C15 1.387(3) .
O3 H1O3 0.802(17) .
C15 C13 1.386(3) 2_565
C15 Cl2 1.730(2) .
C16 O4 1.362(3) .
C16 C17 1.384(3) .
C16 C21 1.392(3) .
O4 H1O4 0.809(18) .
C17 C18 1.394(3) .
C17 Cl3 1.722(2) .
C18 C19 1.385(3) .
C18 Cl4 1.724(2) .
C19 O5 1.354(3) .
C19 C20 1.394(3) .
O5 H1O5 0.811(18) .
C20 C21 1.388(3) .
C20 Cl5 1.725(2) .
C21 Cl6 1.722(2) .
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
N1 H2N1 O5 0.901(17) 2.29(3) 2.987(3) 134(3) 2_676
O5 H1O5 O2 0.811(18) 2.07(3) 2.715(3) 136(3) 1_455
O4 H1O4 O3 0.809(18) 2.24(2) 2.974(3) 151(3) 2_666
O3 H1O3 N2 0.802(17) 1.948(19) 2.709(3) 158(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_4
C7 O1 C1 C6 177.6(2) . .
C7 O1 C1 C2 -3.3(3) . .
C6 C1 C2 N2 -180.0(2) . .
O1 C1 C2 N2 1.0(3) . .
C6 C1 C2 C3 -0.9(4) . .
O1 C1 C2 C3 -179.9(2) . .
N2 C2 C3 C4 177.8(2) . .
C1 C2 C3 C4 -1.3(3) . .
C2 C3 C4 N1 -179.4(2) . .
C2 C3 C4 C5 2.4(4) . .
N1 C4 C5 O2 0.4(3) . .
C3 C4 C5 O2 178.8(2) . .
N1 C4 C5 C6 -179.8(2) . .
C3 C4 C5 C6 -1.4(4) . .
O1 C1 C6 C5 -179.1(2) . .
C2 C1 C6 C5 1.9(4) . .
O2 C5 C6 C1 179.1(2) . .
C4 C5 C6 C1 -0.8(4) . .
C3 C2 N2 C8 -177.3(2) . .
C1 C2 N2 C8 1.8(3) . .
C1 O1 C7 C12 -176.1(2) . .
C1 O1 C7 C8 2.9(3) . .
C2 N2 C8 C9 177.1(2) . .
C2 N2 C8 C7 -2.3(3) . .
O1 C7 C8 N2 0.0(4) . .
C12 C7 C8 N2 178.9(2) . .
O1 C7 C8 C9 -179.4(2) . .
C12 C7 C8 C9 -0.5(4) . .
N2 C8 C9 C10 -178.9(2) . .
C7 C8 C9 C10 0.5(4) . .
C8 C9 C10 C11 -0.2(4) . .
C9 C10 C11 C12 0.0(4) . .
C10 C11 C12 C7 0.0(4) . .
O1 C7 C12 C11 179.2(2) . .
C8 C7 C12 C11 0.3(4) . .
C15 C13 C14 O3 179.6(2) 2_565 .
Cl1 C13 C14 O3 -1.2(3) . .
C15 C13 C14 C15 -0.2(4) 2_565 .
Cl1 C13 C14 C15 178.99(17) . .
O3 C14 C15 C13 -179.6(2) . 2_565
C13 C14 C15 C13 0.2(4) . 2_565
O3 C14 C15 Cl2 0.0(3) . .
C13 C14 C15 Cl2 179.78(16) . .
O4 C16 C17 C18 179.8(2) . .
C21 C16 C17 C18 0.9(4) . .
O4 C16 C17 Cl3 -0.8(3) . .
C21 C16 C17 Cl3 -179.66(18) . .
C16 C17 C18 C19 -0.7(4) . .
Cl3 C17 C18 C19 179.94(19) . .
C16 C17 C18 Cl4 178.97(19) . .
Cl3 C17 C18 Cl4 -0.4(3) . .
C17 C18 C19 O5 179.7(2) . .
Cl4 C18 C19 O5 0.1(3) . .
C17 C18 C19 C20 0.0(4) . .
Cl4 C18 C19 C20 -179.69(19) . .
O5 C19 C20 C21 -179.3(2) . .
C18 C19 C20 C21 0.5(4) . .
O5 C19 C20 Cl5 -0.4(3) . .
C18 C19 C20 Cl5 179.39(18) . .
C19 C20 C21 C16 -0.2(4) . .
Cl5 C20 C21 C16 -179.09(19) . .
C19 C20 C21 Cl6 178.19(19) . .
Cl5 C20 C21 Cl6 -0.7(3) . .
O4 C16 C21 C20 -179.4(2) . .
C17 C16 C21 C20 -0.5(4) . .
O4 C16 C21 Cl6 2.2(3) . .
C17 C16 C21 Cl6 -178.91(18) . .
