#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/45/2234530.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2234530
loop_
_publ_author_name
'Devi, T. Uma'
'Priya, S.'
'Kalpana, G.'
'Selvanayagam, S.'
'Sridhar, B.'
_publ_section_title
;
 Resorcinol ninhydrin complex:
 1,5,9-trihydroxy-8-oxatetracyclo[7.7.0.0^2,7^.0^10,15^]hexadeca-2,4,6,10(15),11,13-hexaen-16-one
;
_journal_coeditor_code           BT5867
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1323
_journal_paper_doi               10.1107/S1600536812014249
_journal_volume                  68
_journal_year                    2012
_chemical_formula_moiety         'C15 H10 O5'
_chemical_formula_sum            'C15 H10 O5'
_chemical_formula_weight         270.23
_chemical_name_systematic
;
1,5,9-trihydroxy-8-oxatetracyclo[7.7.0.0^2,7^.0^10,15^]hexadeca-
2,4,6,10(15),11,13-hexaen-16-one
;
_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                 91.8370(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1117(5)
_cell_length_b                   12.2995(7)
_cell_length_c                   10.1177(5)
_cell_measurement_reflns_used    8468
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      27.1
_cell_measurement_theta_min      2.2
_cell_volume                     1133.30(11)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009)
;
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'ω 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  0.0200
_diffrn_reflns_av_sigmaI/netI    0.0145
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12939
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.24
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.279
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2699
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0391
_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)+(0.0594P)²+0.3056P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1037
_refine_ls_wR_factor_ref         0.1064
_reflns_number_gt                2468
_reflns_number_total             2699
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5867.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2234530
_cod_database_fobs_code          2234530
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_symmetry_multiplicity
O O1 0.55633(10) 0.40497(9) 0.32526(9) 0.0416(2) Uani d 1 1
O O2 0.38544(11) 0.59167(7) 0.40684(9) 0.0382(2) Uani d 1 1
H H2A 0.394(2) 0.5760(16) 0.490(2) 0.058(5) Uiso d 1 1
O O3 0.22262(11) 0.65338(7) 0.19634(9) 0.0369(2) Uani d 1 1
H H3A 0.219(2) 0.689(2) 0.272(2) 0.080(7) Uiso d 1 1
O O4 -0.12067(11) 0.24783(9) 0.55006(10) 0.0444(3) Uani d 1 1
H H4A -0.175(2) 0.2263(19) 0.479(2) 0.076(6) Uiso d 1 1
O O5 0.07320(9) 0.50826(7) 0.24520(8) 0.0336(2) Uani d 1 1
C C1 0.21080(14) 0.48007(11) -0.02647(12) 0.0345(3) Uani d 1 1
H H1 0.1252(19) 0.5225(14) -0.0506(16) 0.042(4) Uiso d 1 1
C C2 0.27738(16) 0.41740(12) -0.12105(13) 0.0409(3) Uani d 1 1
H H2 0.2341(19) 0.4179(14) -0.2090(18) 0.049(4) Uiso d 1 1
C C3 0.40256(16) 0.35623(11) -0.09057(14) 0.0418(3) Uani d 1 1
H H3 0.4472(19) 0.3140(14) -0.1582(17) 0.048(4) Uiso d 1 1
C C4 0.46396(14) 0.35571(10) 0.03612(13) 0.0366(3) Uani d 1 1
H H4 0.5509(18) 0.3132(14) 0.0606(15) 0.041(4) Uiso d 1 1
C C5 0.39742(12) 0.41873(10) 0.13132(11) 0.0301(2) Uani d 1 1
C C6 0.27356(12) 0.48078(9) 0.10008(11) 0.0285(2) Uani d 1 1
C C7 0.44307(12) 0.43593(10) 0.27024(11) 0.0302(2) Uani d 1 1
C C8 0.32381(12) 0.50301(9) 0.33703(11) 0.0283(2) Uani d 1 1
C C9 0.22170(12) 0.54241(9) 0.21795(11) 0.0289(2) Uani d 1 1
C C10 0.22056(12) 0.43138(9) 0.41014(11) 0.0278(2) Uani d 1 1
C C11 0.24218(13) 0.36685(10) 0.52153(11) 0.0310(2) Uani d 1 1
H H11 0.3393(17) 0.3619(12) 0.5676(15) 0.036(4) Uiso d 1 1
C C12 0.12568(14) 0.30692(10) 0.56731(12) 0.0336(3) Uani d 1 1
H H12 0.1362(17) 0.2601(13) 0.6454(16) 0.043(4) Uiso d 1 1
C C13 -0.01040(13) 0.31088(10) 0.50070(12) 0.0328(3) Uani d 1 1
C C14 -0.03552(13) 0.37657(10) 0.39052(12) 0.0331(3) Uani d 1 1
H H14 -0.1314(18) 0.3805(13) 0.3462(15) 0.041(4) Uiso d 1 1
C C15 0.08212(12) 0.43688(10) 0.34892(11) 0.0290(2) Uani d 1 1
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
C8 O2 H2A 109.8(13)
C9 O3 H3A 110.3(15)
C13 O4 H4A 105.4(14)
C15 O5 C9 107.37(8)
C2 C1 C6 117.74(12)
C2 C1 H1 119.7(10)
C6 C1 H1 122.5(10)
C1 C2 C3 121.46(12)
C1 C2 H2 117.4(10)
C3 C2 H2 121.1(10)
C4 C3 C2 120.81(12)
C4 C3 H3 119.4(10)
C2 C3 H3 119.8(10)
C3 C4 C5 117.86(12)
C3 C4 H4 122.6(9)
C5 C4 H4 119.5(9)
C6 C5 C4 121.15(11)
C6 C5 C7 109.97(10)
C4 C5 C7 128.83(11)
C1 C6 C5 120.97(11)
C1 C6 C9 127.29(11)
C5 C6 C9 111.73(10)
O1 C7 C5 127.04(11)
O1 C7 C8 124.56(11)
C5 C7 C8 108.39(9)
O2 C8 C10 117.01(9)
O2 C8 C7 111.12(9)
C10 C8 C7 111.37(9)
O2 C8 C9 111.24(9)
C10 C8 C9 101.15(9)
C7 C8 C9 103.73(9)
O3 C9 O5 109.04(9)
O3 C9 C6 111.66(9)
O5 C9 C6 108.88(9)
O3 C9 C8 114.73(9)
O5 C9 C8 107.28(9)
C6 C9 C8 105.01(9)
C11 C10 C15 119.57(11)
C11 C10 C8 131.39(10)
C15 C10 C8 109.04(10)
C12 C11 C10 119.08(11)
C12 C11 H11 119.6(9)
C10 C11 H11 121.3(9)
C11 C12 C13 119.98(11)
C11 C12 H12 121.8(9)
C13 C12 H12 118.2(9)
O4 C13 C14 121.03(11)
O4 C13 C12 116.99(11)
C14 C13 C12 121.97(11)
C15 C14 C13 116.58(11)
C15 C14 H14 121.9(9)
C13 C14 H14 121.5(9)
O5 C15 C14 123.43(10)
O5 C15 C10 113.82(10)
C14 C15 C10 122.74(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.2178(14)
O2 C8 1.4063(14)
O2 H2A 0.87(2)
O3 C9 1.3823(14)
O3 H3A 0.89(2)
O4 C13 1.3756(15)
O4 H4A 0.90(2)
O5 C15 1.3686(14)
O5 C9 1.4516(14)
C1 C2 1.3839(19)
C1 C6 1.3855(16)
C1 H1 0.964(17)
C2 C3 1.393(2)
C2 H2 0.962(18)
C3 C4 1.382(2)
C3 H3 0.960(17)
C4 C5 1.3907(17)
C4 H4 0.975(17)
C5 C6 1.3904(16)
C5 C7 1.4683(16)
C6 C9 1.5021(16)
C7 C8 1.5379(16)
C8 C10 1.5011(16)
C8 C9 1.5749(15)
C10 C11 1.3873(16)
C10 C15 1.3890(15)
C11 C12 1.3843(17)
C11 H11 0.989(16)
C12 C13 1.3930(18)
C12 H12 0.979(17)
C13 C14 1.3899(18)
C14 C15 1.3803(17)
C14 H14 0.970(16)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O4 H4A O3 2_545 0.90(2) 2.02(2) 2.8770(10) 158(2)
O3 H3A O4 3_566 0.89(2) 2.18(2) 3.0130(10) 157(2)
O2 H2A O1 3_666 0.87(2) 1.92(2) 2.7460(10) 159(2)
O3 H3A O2 . 0.89(2) 2.33(2) 2.6670(10) 102.0(10)
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
C6 C1 C2 C3 0.49(19)
C1 C2 C3 C4 0.4(2)
C2 C3 C4 C5 -0.50(19)
C3 C4 C5 C6 -0.34(18)
C3 C4 C5 C7 -177.34(12)
C2 C1 C6 C5 -1.33(18)
C2 C1 C6 C9 179.74(11)
C4 C5 C6 C1 1.28(18)
C7 C5 C6 C1 178.80(10)
C4 C5 C6 C9 -179.63(10)
C7 C5 C6 C9 -2.12(13)
C6 C5 C7 O1 -170.36(12)
C4 C5 C7 O1 6.9(2)
C6 C5 C7 C8 8.49(13)
C4 C5 C7 C8 -174.24(11)
O1 C7 C8 O2 48.37(15)
C5 C7 C8 O2 -130.52(10)
O1 C7 C8 C10 -84.00(14)
C5 C7 C8 C10 97.11(10)
O1 C7 C8 C9 167.98(11)
C5 C7 C8 C9 -10.91(11)
C15 O5 C9 O3 -136.72(9)
C15 O5 C9 C6 101.24(10)
C15 O5 C9 C8 -11.91(12)
C1 C6 C9 O3 -60.94(15)
C5 C6 C9 O3 120.05(11)
C1 C6 C9 O5 59.51(15)
C5 C6 C9 O5 -119.51(10)
C1 C6 C9 C8 174.14(11)
C5 C6 C9 C8 -4.88(12)
O2 C8 C9 O3 5.95(14)
C10 C8 C9 O3 130.92(10)
C7 C8 C9 O3 -113.58(10)
O2 C8 C9 O5 -115.34(10)
C10 C8 C9 O5 9.63(11)
C7 C8 C9 O5 125.13(9)
O2 C8 C9 C6 128.92(10)
C10 C8 C9 C6 -106.11(10)
C7 C8 C9 C6 9.39(11)
O2 C8 C10 C11 -62.49(17)
C7 C8 C10 C11 66.83(15)
C9 C8 C10 C11 176.52(12)
O2 C8 C10 C15 116.84(11)
C7 C8 C10 C15 -113.83(10)
C9 C8 C10 C15 -4.14(12)
C15 C10 C11 C12 1.69(17)
C8 C10 C11 C12 -179.04(11)
C10 C11 C12 C13 0.81(18)
C11 C12 C13 O4 178.84(11)
C11 C12 C13 C14 -2.16(18)
O4 C13 C14 C15 179.85(11)
C12 C13 C14 C15 0.90(18)
C9 O5 C15 C14 -170.98(11)
C9 O5 C15 C10 9.76(13)
C13 C14 C15 O5 -177.48(10)
C13 C14 C15 C10 1.71(17)
C11 C10 C15 O5 176.22(10)
C8 C10 C15 O5 -3.20(13)
C11 C10 C15 C14 -3.04(18)
C8 C10 C15 C14 177.54(10)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 3333317
