#------------------------------------------------------------------------------
#$Date: 2016-07-23 04:14:04 +0300 (Sat, 23 Jul 2016) $
#$Revision: 184618 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/17/2241778.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_2241778
loop_
_publ_author_name
'Bauri, A. K.'
'Foro, Sabine'
'Nhu Do, Quynh Nguyen'
_publ_section_title
;
 Crystal structure of bergapten: a photomutagenic and photobiologically
 active furanocoumarin
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1194
_journal_page_last               1196
_journal_paper_doi               10.1107/S2056989016011221
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          'C12 H8 O4'
_chemical_formula_moiety         'C12 H8 O4'
_chemical_formula_sum            'C12 H8 O4'
_chemical_formula_weight         216.18
_chemical_melting_point          469
_chemical_name_common            Bergapten
_chemical_name_systematic
;
4-Methoxy-7H-furo[3,2-g]chromen-7-one
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 92.12(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.8486(8)
_cell_length_b                   14.676(2)
_cell_length_c                   16.866(3)
_cell_measurement_reflns_used    870
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      27.90
_cell_measurement_theta_min      2.78
_cell_volume                     952.0(3)
_computing_cell_refinement
;
CrysAlis CCD (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
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS2014 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      299(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur 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  0.08
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7096
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         2.776
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)'
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_description       needle
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.222
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.855
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         7096
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.855
_refine_ls_R_factor_all          0.1088
_refine_ls_R_factor_gt           0.0546
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0738P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1223
_refine_ls_wR_factor_ref         0.1377
_reflns_number_gt                3811
_reflns_number_total             7096
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            su5310sup1.cif
_cod_data_source_block           I
_cod_database_code               2241778
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.951
_shelx_estimated_absorpt_t_max   0.998
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_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
O O1 0.7447(9) 0.00489(18) 0.37565(18) 0.0525(10) Uani d 1
O O2 0.3156(8) 0.26727(18) 0.50579(14) 0.0399(9) Uani d 1
O O3 0.7860(9) 0.28906(17) 0.24893(16) 0.0510(10) Uani d 1
O O4 0.1046(9) 0.3863(2) 0.56614(18) 0.0617(11) Uani d 1
C C1 0.6682(13) 0.0956(3) 0.3822(3) 0.0392(13) Uani d 1
C C2 0.8854(13) -0.0043(3) 0.3016(3) 0.0534(15) Uani d 1
H H2 0.9619 -0.0595 0.2814 0.064 Uiso calc 1
C C3 0.8989(13) 0.0740(3) 0.2626(3) 0.0477(14) Uani d 1
H H3 0.9832 0.0833 0.2123 0.057 Uiso calc 1
C C4 0.7573(13) 0.1417(3) 0.3137(2) 0.0369(12) Uani d 1
C C5 0.6975(12) 0.2354(3) 0.3111(2) 0.0344(12) Uani d 1
C C6 0.5523(11) 0.2781(3) 0.3757(2) 0.0304(11) Uani d 1
C C7 0.4677(11) 0.2262(3) 0.4418(2) 0.0348(12) Uani d 1
C C8 0.5234(12) 0.1339(3) 0.4477(3) 0.0397(13) Uani d 1
H H8 0.4679 0.1003 0.4922 0.048 Uiso calc 1
C C9 0.4692(12) 0.3738(3) 0.3771(3) 0.0373(13) Uani d 1
H H9 0.5221 0.4101 0.3339 0.045 Uiso calc 1
C C10 0.3191(12) 0.4114(3) 0.4385(2) 0.0431(13) Uani d 1
H H10 0.2654 0.4732 0.4371 0.052 Uiso calc 1
C C11 0.2370(13) 0.3592(3) 0.5074(3) 0.0433(13) Uani d 1
C C12 0.6549(14) 0.2653(3) 0.1726(2) 0.0652(17) Uani d 1
H H12A 0.7936 0.2173 0.1516 0.098 Uiso calc 1
H H12B 0.6630 0.3175 0.1384 0.098 Uiso calc 1
H H12C 0.4187 0.2450 0.1758 0.098 Uiso calc 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
C1 O1 C2 105.1(3)
C7 O2 C11 122.6(3)
C5 O3 C12 117.9(3)
O1 C1 C8 123.8(4)
O1 C1 C4 110.2(4)
C8 C1 C4 126.0(4)
C3 C2 O1 112.7(4)
C3 C2 H2 123.7
O1 C2 H2 123.7
C2 C3 C4 106.2(4)
C2 C3 H3 126.9
C4 C3 H3 126.9
C5 C4 C1 117.3(4)
C5 C4 C3 136.9(4)
C1 C4 C3 105.8(4)
O3 C5 C6 117.4(4)
O3 C5 C4 123.2(4)
C6 C5 C4 119.4(4)
C5 C6 C7 119.4(4)
C5 C6 C9 123.2(4)
C7 C6 C9 117.4(4)
C8 C7 O2 116.2(4)
C8 C7 C6 123.7(4)
O2 C7 C6 120.1(4)
C1 C8 C7 114.2(4)
C1 C8 H8 122.9
C7 C8 H8 122.9
C10 C9 C6 121.4(4)
C10 C9 H9 119.3
C6 C9 H9 119.3
C9 C10 C11 121.7(4)
C9 C10 H10 119.1
C11 C10 H10 119.1
O4 C11 O2 116.1(4)
O4 C11 C10 127.2(4)
O2 C11 C10 116.8(4)
O3 C12 H12A 109.5
O3 C12 H12B 109.5
H12A C12 H12B 109.5
O3 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.369(5)
O1 C2 1.386(5)
O2 C7 1.385(4)
O2 C11 1.383(5)
O3 C5 1.365(4)
O3 C12 1.409(4)
O4 C11 1.200(5)
C1 C8 1.376(5)
C1 C4 1.393(6)
C2 C3 1.327(6)
C2 H2 0.9300
C3 C4 1.435(6)
C3 H3 0.9300
C4 C5 1.394(6)
C5 C6 1.391(5)
C6 C7 1.398(5)
C6 C9 1.442(5)
C7 C8 1.374(5)
C8 H8 0.9300
C9 C10 1.325(5)
C9 H9 0.9300
C10 C11 1.435(5)
C10 H10 0.9300
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 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
C2 H2 O3 2_745 0.93 2.49 3.406(5) 170
C3 H3 O4 4_665 0.93 2.57 3.484(6) 170
C10 H10 O4 3_566 0.93 2.51 3.387(5) 158
C12 H12A O4 4_665 0.96 2.44 3.376(5) 165
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 C8 -179.8(5)
C2 O1 C1 C4 0.3(5)
C1 O1 C2 C3 -0.2(6)
O1 C2 C3 C4 0.0(6)
O1 C1 C4 C5 -179.6(4)
C8 C1 C4 C5 0.5(7)
O1 C1 C4 C3 -0.3(5)
C8 C1 C4 C3 179.8(5)
C2 C3 C4 C5 179.2(6)
C2 C3 C4 C1 0.2(6)
C12 O3 C5 C6 -126.8(4)
C12 O3 C5 C4 55.5(6)
C1 C4 C5 O3 177.3(4)
C3 C4 C5 O3 -1.7(9)
C1 C4 C5 C6 -0.3(7)
C3 C4 C5 C6 -179.3(5)
O3 C5 C6 C7 -178.0(4)
C4 C5 C6 C7 -0.3(6)
O3 C5 C6 C9 4.7(6)
C4 C5 C6 C9 -177.6(4)
C11 O2 C7 C8 -178.5(4)
C11 O2 C7 C6 0.9(6)
C5 C6 C7 C8 0.8(6)
C9 C6 C7 C8 178.3(4)
C5 C6 C7 O2 -178.5(4)
C9 C6 C7 O2 -1.1(6)
O1 C1 C8 C7 -179.9(5)
C4 C1 C8 C7 -0.1(7)
O2 C7 C8 C1 178.7(4)
C6 C7 C8 C1 -0.6(7)
C5 C6 C9 C10 177.4(5)
C7 C6 C9 C10 0.1(7)
C6 C9 C10 C11 1.1(7)
C7 O2 C11 O4 179.7(4)
C7 O2 C11 C10 0.3(6)
C9 C10 C11 O4 179.3(5)
C9 C10 C11 O2 -1.3(7)

_cod_database_fobs_code 2241778
