#------------------------------------------------------------------------------
#$Date: 2017-07-25 12:38:30 +0300 (Tue, 25 Jul 2017) $
#$Revision: 199156 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/21/2242186.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_2242186
loop_
_publ_author_name
'Bauri, A. K.'
'Foro, Sabine'
'Rahman, A. F. M. M.'
_publ_section_title
;
 Crystal structure of dibromomethoxyseselin (DBMS), a photobiologically
 active pyranocoumarin
;
_journal_coeditor_code           LH5842
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              774
_journal_page_last               776
_journal_paper_doi               10.1107/S2056989017006132
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C15 H14 Br2 O4'
_chemical_formula_moiety         'C15 H14 Br2 O4'
_chemical_formula_sum            'C15 H14 Br2 O4'
_chemical_formula_weight         418.08
_chemical_name_common            'Dibromo Methoxy Seselin (DBMS)'
_chemical_name_systematic
rac-(9S,10R)-3,9-Dibromo-10-methoxy-8,8-dimethyl-9,10-dihydropyrano[2,3-h]chromen-2(8H)-one
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                105.34(2)
_cell_angle_beta                 90.450(10)
_cell_angle_gamma                103.38(2)
_cell_formula_units_Z            2
_cell_length_a                   7.1190(10)
_cell_length_b                   8.5190(10)
_cell_length_c                   13.366(2)
_cell_measurement_reflns_used    2165
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      27.89
_cell_measurement_theta_min      2.56
_cell_volume                     758.4(2)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      299(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur single-crystal X-ray diffractometer
with a Sapphire CCD detector
;
_diffrn_measurement_method
;
Rotation method data acquisition using omega and phi 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  0.0148
_diffrn_reflns_av_sigmaI/netI    0.0279
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5172
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.56
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    5.356
_exptl_absorpt_correction_T_max  0.4234
_exptl_absorpt_correction_T_min  0.3642
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.831
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.421
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.849
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2764
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.849
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0347
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1162
_reflns_number_gt                2144
_reflns_number_total             2764
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5842sup1.cif
_cod_data_source_block           I
_cod_database_code               2242186
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
Br Br1 1.17651(6) 0.02924(6) 0.16407(4) 0.04731(18) Uani d . 1 1
Br Br2 0.74960(8) 0.46658(6) 0.74871(4) 0.0602(2) Uani d . 1 1
O O1 0.8143(4) -0.2513(3) 0.2144(2) 0.0405(7) Uani d . 1 1
O O2 0.7746(4) 0.2766(3) 0.4357(2) 0.0399(7) Uani d . 1 1
O O3 0.6525(4) 0.1428(3) 0.2086(2) 0.0416(7) Uani d . 1 1
O O4 0.7816(6) 0.5300(4) 0.5337(3) 0.0694(11) Uani d . 1 1
C C1 0.7877(5) -0.1487(5) 0.3085(3) 0.0322(8) Uani d . 1 1
C C2 0.7930(6) -0.1956(5) 0.1231(3) 0.0407(9) Uani d . 1 1
C C3 0.8945(5) -0.0109(5) 0.1422(3) 0.0345(8) Uani d . 1 1
H H3 0.8663 0.0240 0.0807 0.041 Uiso calc R 1 1
C C4 0.8264(5) 0.1028(5) 0.2368(3) 0.0319(8) Uani d . 1 1
H H4 0.9274 0.2070 0.2619 0.038 Uiso calc R 1 1
C C5 0.7908(5) 0.0188(5) 0.3224(3) 0.0305(8) Uani d . 1 1
C C6 0.7703(5) 0.1103(4) 0.4232(3) 0.0299(8) Uani d . 1 1
C C7 0.7715(6) 0.3884(5) 0.5309(3) 0.0437(10) Uani d . 1 1
C C8 0.7530(6) 0.3147(5) 0.6187(3) 0.0357(9) Uani d . 1 1
C C9 0.7392(5) 0.1528(5) 0.6078(3) 0.0352(9) Uani d . 1 1
H H9 0.7232 0.1108 0.6656 0.042 Uiso calc R 1 1
C C10 0.7488(5) 0.0428(5) 0.5074(3) 0.0305(8) Uani d . 1 1
C C11 0.7447(5) -0.1286(5) 0.4888(3) 0.0345(9) Uani d . 1 1
H H11 0.7290 -0.1781 0.5435 0.041 Uiso calc R 1 1
C C12 0.7636(6) -0.2230(5) 0.3909(3) 0.0355(9) Uani d . 1 1
H H12 0.7605 -0.3362 0.3790 0.043 Uiso calc R 1 1
C C13 0.5762(7) -0.2223(6) 0.0942(4) 0.0553(12) Uani d . 1 1
H H13A 0.5609 -0.1819 0.0348 0.066 Uiso calc R 1 1
H H13B 0.5182 -0.1619 0.1518 0.066 Uiso calc R 1 1
H H13C 0.5142 -0.3397 0.0780 0.066 Uiso calc R 1 1
C C14 0.8775(8) -0.3121(6) 0.0381(4) 0.0590(13) Uani d . 1 1
H H14A 1.0133 -0.2949 0.0553 0.071 Uiso calc R 1 1
H H14B 0.8597 -0.2880 -0.0270 0.071 Uiso calc R 1 1
H H14C 0.8128 -0.4265 0.0325 0.071 Uiso calc R 1 1
C C15 0.6827(8) 0.2953(7) 0.1849(5) 0.0697(16) Uani d . 1 1
H H15A 0.7553 0.3827 0.2421 0.084 Uiso calc R 1 1
H H15B 0.5602 0.3182 0.1723 0.084 Uiso calc R 1 1
H H15C 0.7537 0.2904 0.1238 0.084 Uiso calc R 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'
Br Br -0.2901 2.4595 '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
C1 O1 C2 117.6(3)
C6 O2 C7 123.4(3)
C15 O3 C4 114.0(3)
O1 C1 C5 122.4(3)
O1 C1 C12 115.6(3)
C5 C1 C12 122.0(3)
O1 C2 C3 111.0(3)
O1 C2 C14 104.5(3)
C3 C2 C14 113.4(3)
O1 C2 C13 109.0(3)
C3 C2 C13 109.7(3)
C14 C2 C13 109.1(4)
C2 C3 C4 113.0(3)
C2 C3 Br1 112.1(3)
C4 C3 Br1 107.3(3)
C2 C3 H3 108.1
C4 C3 H3 108.1
Br1 C3 H3 108.1
O3 C4 C5 109.4(3)
O3 C4 C3 110.3(3)
C5 C4 C3 110.5(3)
O3 C4 H4 108.8
C5 C4 H4 108.8
C3 C4 H4 108.8
C1 C5 C6 116.3(3)
C1 C5 C4 122.9(3)
C6 C5 C4 120.7(3)
O2 C6 C10 120.6(3)
O2 C6 C5 115.6(3)
C10 C6 C5 123.8(3)
O4 C7 O2 118.2(4)
O4 C7 C8 127.1(4)
O2 C7 C8 114.7(3)
C9 C8 C7 122.9(4)
C9 C8 Br2 122.2(3)
C7 C8 Br2 114.9(3)
C8 C9 C10 120.1(4)
C8 C9 H9 119.9
C10 C9 H9 119.9
C6 C10 C11 117.6(3)
C6 C10 C9 118.1(3)
C11 C10 C9 124.3(3)
C12 C11 C10 120.4(3)
C12 C11 H11 119.8
C10 C11 H11 119.8
C11 C12 C1 119.9(3)
C11 C12 H12 120.0
C1 C12 H12 120.0
C2 C13 H13A 109.5
C2 C13 H13B 109.5
H13A C13 H13B 109.5
C2 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C2 C14 H14A 109.5
C2 C14 H14B 109.5
H14A C14 H14B 109.5
C2 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
O3 C15 H15A 109.5
O3 C15 H15B 109.5
H15A C15 H15B 109.5
O3 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C3 1.963(4)
Br2 C8 1.876(4)
O1 C1 1.371(4)
O1 C2 1.440(5)
O2 C6 1.375(4)
O2 C7 1.377(5)
O3 C15 1.386(5)
O3 C4 1.431(4)
O4 C7 1.183(5)
C1 C5 1.384(5)
C1 C12 1.401(5)
C2 C3 1.524(6)
C2 C14 1.526(5)
C2 C13 1.538(6)
C3 C4 1.533(5)
C3 H3 0.9800
C4 C5 1.496(5)
C4 H4 0.9800
C5 C6 1.394(5)
C6 C10 1.388(5)
C7 C8 1.463(6)
C8 C9 1.328(5)
C9 C10 1.432(5)
C9 H9 0.9300
C10 C11 1.408(5)
C11 C12 1.369(5)
C11 H11 0.9300
C12 H12 0.9300
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
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
C11 H11 O4 1_545 0.93 2.57 3.188(6) 124
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
C2 O1 C1 C5 -16.8(6)
C2 O1 C1 C12 165.3(3)
C1 O1 C2 C3 44.2(5)
C1 O1 C2 C14 166.8(3)
C1 O1 C2 C13 -76.7(4)
O1 C2 C3 C4 -55.3(4)
C14 C2 C3 C4 -172.6(4)
C13 C2 C3 C4 65.1(4)
O1 C2 C3 Br1 66.0(3)
C14 C2 C3 Br1 -51.3(4)
C13 C2 C3 Br1 -173.5(3)
C15 O3 C4 C5 142.1(4)
C15 O3 C4 C3 -96.1(4)
C2 C3 C4 O3 -83.3(4)
Br1 C3 C4 O3 152.6(2)
C2 C3 C4 C5 37.8(4)
Br1 C3 C4 C5 -86.2(3)
O1 C1 C5 C6 -177.2(3)
C12 C1 C5 C6 0.5(6)
O1 C1 C5 C4 -1.0(6)
C12 C1 C5 C4 176.8(3)
O3 C4 C5 C1 111.1(4)
C3 C4 C5 C1 -10.6(5)
O3 C4 C5 C6 -72.7(4)
C3 C4 C5 C6 165.6(3)
C7 O2 C6 C10 4.5(6)
C7 O2 C6 C5 -174.8(3)
C1 C5 C6 O2 179.7(3)
C4 C5 C6 O2 3.4(5)
C1 C5 C6 C10 0.4(6)
C4 C5 C6 C10 -176.0(3)
C6 O2 C7 O4 177.8(4)
C6 O2 C7 C8 -3.0(6)
O4 C7 C8 C9 178.8(5)
O2 C7 C8 C9 -0.3(6)
O4 C7 C8 Br2 -1.1(7)
O2 C7 C8 Br2 179.8(3)
C7 C8 C9 C10 2.2(6)
Br2 C8 C9 C10 -178.0(3)
O2 C6 C10 C11 179.7(3)
C5 C6 C10 C11 -1.0(6)
O2 C6 C10 C9 -2.5(5)
C5 C6 C10 C9 176.8(3)
C8 C9 C10 C6 -0.8(6)
C8 C9 C10 C11 176.9(4)
C6 C10 C11 C12 0.7(5)
C9 C10 C11 C12 -177.0(4)
C10 C11 C12 C1 0.1(6)
O1 C1 C12 C11 177.1(3)
C5 C1 C12 C11 -0.8(6)

_cod_database_fobs_code 2242186
