#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/54/2215479.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_2215479
loop_
_publ_author_name
'Urban, Jiří'
'Fábry, Jan'
'Zuman, Petr'
'Ludvík, Jiří'
'Císařová, Ivana'
_publ_section_title
(3R*,1'S*,3'R*)-3-(3'-Hydroxy-1'H,3'H-benzo[c]furan-1'-yl)-2-(2''-hydroxyethyl)-2,3-dihydro-1H-benzo[c]pyrrol-1-one
_journal_coeditor_code           GG2023
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4139
_journal_page_last               o4140
_journal_paper_doi               10.1107/S1600536807045308
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C18 H17 N1 O4'
_chemical_formula_moiety         'C18 H17 N1 O4'
_chemical_formula_sum            'C18 H17 N O4'
_chemical_formula_weight         311.3
_chemical_name_common
;
(3R*,1'S*,3'R*)-2-(2''-hydroxyethyl)-3-
(3'-hydroxy-1'H,3'H-
benzo[c]furan)-1'-yl-1H,3H-benzo[c]pyrrol-1-one
;
_chemical_name_systematic
;
(3R*,1'S*,3'R*)-3-(3'-Hydroxy-1'H,3'H-
benzo[c]furan-1'-yl)-2-(2''-hydroxyethyl)-2,3-dihydro-1H-
benzo[c]pyrrol-1-one
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.02920(10)
_cell_length_b                   11.9861(5)
_cell_length_c                   18.0014(7)
_cell_measurement_reflns_used    1756
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.02
_cell_measurement_theta_min      1
_cell_volume                     1516.67(9)
_computing_cell_refinement
;
COLLECT (Nonius, 1998) and DENZO (Otwinowski & Minor, 1997)
;
_computing_data_collection
;
COLLECT (Nonius, 1998) and DENZO (Otwinowski & Minor, 1997)
;
_computing_data_reduction
;
COLLECT (Nonius, 1998) and DENZO (Otwinowski & Minor, 1997)
;
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material
'JANA2000 (Petříček et al.,  2000)'
_computing_structure_refinement
'JANA2000 (Petříček et al.,  2000)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.058
_diffrn_reflns_av_sigmaI/netI    0.0331
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18223
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.16
_refine_diff_density_min         -0.17
_refine_ls_extinction_coef       1.57(16)
_refine_ls_extinction_method
'B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974)'
_refine_ls_goodness_of_fit_ref   1.65
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_constraints    60
_refine_ls_number_parameters     217
_refine_ls_number_reflns         1737
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.0056
_refine_ls_shift/su_mean         0.0006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 1/(σ²(I)+0.0004I²)'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.0663
_refine_ls_wR_factor_ref         0.0693
_reflns_number_gt                1482
_reflns_number_total             1737
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg2023.cif
_cod_data_source_block           I
_cod_original_formula_sum        'C18 H17 N1 O4'
_cod_database_code               2215479
_cod_database_fobs_code          2215479
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,1/2+y,1/2-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_occupancy
C C1 0.6319(3) 0.35574(19) 0.31944(13) 0.0247(7) Uani d 1
O O1 0.4921(2) 0.36611(15) 0.36055(9) 0.0344(6) Uani d 1
N N2 0.7803(2) 0.28509(16) 0.33170(10) 0.0228(6) Uani d 1
C C3 0.9250(3) 0.28969(18) 0.27316(12) 0.0223(7) Uani d 1
H H3 1.049523 0.313389 0.291876 0.0268 Uiso d 1
C C4a 0.8429(3) 0.37409(19) 0.22012(12) 0.0229(7) Uani d 1
C C7a 0.6721(3) 0.41363(19) 0.24872(13) 0.0243(7) Uani d 1
C C4 0.9105(3) 0.41434(19) 0.15273(12) 0.0254(8) Uani d 1
H H4 1.025186 0.389264 0.133152 0.0305 Uiso d 1
C C5 0.8021(3) 0.49305(18) 0.11539(13) 0.0286(8) Uani d 1
H H5 0.843911 0.519653 0.069689 0.0344 Uiso d 1
C C6 0.6330(3) 0.5332(2) 0.14428(13) 0.0304(8) Uani d 1
H H6 0.564561 0.58684 0.118234 0.0364 Uiso d 1
C C7 0.5651(3) 0.49403(19) 0.21169(13) 0.0300(8) Uani d 1
H H7 0.451645 0.520785 0.231403 0.036 Uiso d 1
O O2' 0.8001(2) 0.13188(13) 0.20416(8) 0.0284(5) Uani d 1
C C3' 0.8425(3) 0.09010(18) 0.13168(13) 0.0256(7) Uani d 1
H H3' 0.742632 0.110399 0.096186 0.0307 Uiso d 1
C C4'a 1.0382(3) 0.13391(19) 0.11551(12) 0.0221(7) Uani d 1
C C7'a 1.1135(3) 0.18025(19) 0.17942(13) 0.0222(7) Uani d 1
C C1' 0.9675(3) 0.17481(19) 0.23995(12) 0.0239(7) Uani d 1
H H1' 1.008275 0.125368 0.280284 0.0286 Uiso d 1
C C4' 1.1405(3) 0.13336(19) 0.04959(13) 0.0297(8) Uani d 1
H H4' 1.091314 0.100496 0.006917 0.0356 Uiso d 1
C C5' 1.3188(3) 0.18345(19) 0.04942(14) 0.0322(8) Uani d 1
H H5' 1.388937 0.18607 0.005654 0.0387 Uiso d 1
C C6' 1.3937(3) 0.2297(2) 0.11368(14) 0.0310(8) Uani d 1
H H6' 1.513096 0.262987 0.112345 0.0372 Uiso d 1
C C7' 1.2934(3) 0.22706(19) 0.17991(14) 0.0271(8) Uani d 1
H H7' 1.345299 0.255859 0.223395 0.0325 Uiso d 1
O O3 0.8433(2) -0.02678(14) 0.13010(10) 0.0316(6) Uani d 1
H H3O 0.737(2) -0.055(3) 0.131(2) 0.107(14) Uiso d 1
C C1'' 0.7943(3) 0.21383(19) 0.39678(12) 0.0254(7) Uani d 1
H H1''a 0.675818 0.216763 0.424362 0.0304 Uiso d 1
H H1''b 0.807196 0.136731 0.381209 0.0304 Uiso d 1
C C2'' 0.9573(3) 0.24420(19) 0.44749(13) 0.0278(8) Uani d 1
H H2''a 0.963299 0.191412 0.488262 0.0334 Uiso d 1
H H2''b 1.076237 0.238248 0.420462 0.0334 Uiso d 1
O O4 0.9379(3) 0.35389(15) 0.47616(10) 0.0349(6) Uani d 1
H H4O 0.993(4) 0.395(2) 0.4465(14) 0.086(14) Uiso d 1
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.003 0.002 'International Tables Vol C Tables  4.2.6.8 and 6.1.1.4'
H 0.000 0.000 'International Tables Vol C Tables  4.2.6.8 and 6.1.1.4'
N 0.006 0.003 'International Tables Vol C Tables  4.2.6.8 and 6.1.1.4'
O 0.011 0.006 '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_publ_flag
O1 C1 N2 125.1(2) no
O1 C1 C7a 128.4(2) no
N2 C1 C7a 106.57(18) no
C1 N2 C3 113.06(18) no
C1 N2 C1'' 123.23(18) no
C3 N2 C1'' 123.70(17) no
N2 C3 C4a 102.43(16) no
N2 C3 C1' 112.48(17) no
C4a C3 C1' 115.56(18) no
C3 C4a C7a 108.98(18) no
C3 C4a C4 130.99(19) no
C7a C4a C4 120.0(2) no
C1 C7a C4a 108.93(19) no
C1 C7a C7 129.4(2) no
C4a C7a C7 121.7(2) no
C4a C4 C5 118.2(2) no
C4 C5 C6 121.8(2) no
C5 C6 C7 120.5(2) no
C7a C7 C6 117.9(2) no
C3' O2' C1' 111.36(15) no
O2' C3' C4'a 104.22(17) no
O2' C3' O3 111.69(18) no
C4'a C3' O3 110.02(18) no
C3' C4'a C7'a 109.29(19) no
C3' C4'a C4' 129.7(2) no
C7'a C4'a C4' 120.97(19) no
C4'a C7'a C1' 108.97(17) no
C4'a C7'a C7' 121.2(2) no
C1' C7'a C7' 129.7(2) no
C3 C1' O2' 109.73(16) no
C3 C1' C7'a 112.24(18) no
O2' C1' C7'a 104.50(17) no
C4'a C4' C5' 117.9(2) no
C4' C5' C6' 120.9(2) no
C5' C6' C7' 121.1(2) no
C7'a C7' C6' 117.9(2) no
N2 C1'' C2'' 113.39(18) no
C1'' C2'' O4 111.75(19) no
H1''a C1'' H1''b 105.2 no
H2''a C2'' H2''b 107.1 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 1.237(3) no
C1 N2 1.362(3) no
C1 C7a 1.477(3) no
N2 C3 1.466(3) no
N2 C1'' 1.453(3) no
C3 C4a 1.506(3) no
C3 C1' 1.531(3) no
C4a C7a 1.390(3) no
C4a C4 1.389(3) no
C7a C7 1.392(3) no
C4 C5 1.387(3) no
C5 C6 1.384(3) no
C6 C7 1.386(3) no
O2' C3' 1.429(3) no
O2' C1' 1.437(3) no
C3' C4'a 1.501(3) no
C3' O3 1.401(3) no
C4'a C7'a 1.383(3) no
C4'a C4' 1.388(3) no
C7'a C1' 1.499(3) no
C7'a C7' 1.383(3) no
C4' C5' 1.389(3) no
C5' C6' 1.387(3) no
C6' C7' 1.385(3) no
C1'' C2'' 1.510(3) no
C2'' O4 1.419(3) no
C3 H3 0.98 no
C4 H4 0.93 no
C5 H5 0.93 no
C6 H6 0.93 no
C7 H7 0.93 no
C3' H3' 0.98 no
C1' H1' 0.98 no
C4' H4' 0.93 no
C5' H5' 0.93 no
C6' H6' 0.93 no
C7' H7' 0.93 no
O3 H3O 0.82(2) no
C1'' H1''a 0.97 no
C1'' H1''b 0.97 no
C2'' H2''a 0.97 no
C2'' H2''b 0.97 no
O4 H4O 0.82(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21184243
2 PubChem 139073120
