#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/46/2204641.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_2204641
loop_
_publ_author_name
'Huo, Fangjun'
'Yin, Caixia'
'Yang, Pin'
_publ_section_title
;
 7-Methoxy-2,3-dihydro-1H-cyclopenta[b]chromen-1-one
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2278
_journal_page_last               o2280
_journal_paper_doi               10.1107/S1600536804028478
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C13 H12 O3'
_chemical_formula_moiety         'C13 H12 O3'
_chemical_formula_sum            'C13 H12 O3'
_chemical_formula_weight         216.23
_chemical_name_common
;
7-Methoxy-2,3-dihydro-1H-cyclopenta[b]chromen-1-one
;
_chemical_name_systematic
;
7-Methoxy-2,3-dihydro-1H-cyclopenta[b]chromen-1-one
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.0201(9)
_cell_length_b                   12.0980(13)
_cell_length_c                   22.173(3)
_cell_measurement_reflns_used    13031
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.91
_cell_measurement_theta_min      3.14
_cell_volume                     2151.4(4)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 2000)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean '100x100 microns'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       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  0.0472
_diffrn_reflns_av_sigmaI/netI    0.0296
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            8308
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.84
_diffrn_standards_decay_%        2.89
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.9813
_exptl_absorpt_correction_T_min  0.9722
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.271
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1898
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0576
_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)+(0.0672P)²+0.428P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1344
_refine_ls_wR_factor_ref         0.1434
_reflns_number_gt                1547
_reflns_number_total             1898
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci6480.cif
_cod_data_source_block           I
_cod_original_cell_volume        2151.3(4)
_cod_database_code               2204641
_cod_database_fobs_code          2204641
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_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_type_symbol
O3 0.8193(2) 0.12170(13) 0.96804(6) 0.0639(5) Uani d . 1 O
O2 0.96890(17) -0.08808(11) 0.75368(6) 0.0484(4) Uani d . 1 O
O1 0.8236(2) 0.18406(13) 0.61160(6) 0.0727(6) Uani d . 1 O
C9 0.8508(2) 0.07645(17) 0.91255(8) 0.0452(5) Uani d . 1 C
C10 0.9243(2) -0.02710(17) 0.91317(9) 0.0484(5) Uani d . 1 C
H10 0.9497 -0.0604 0.9498 0.058 Uiso calc R 1 H
C11 0.9602(2) -0.08135(16) 0.86017(9) 0.0464(5) Uani d . 1 C
H11 1.0100 -0.1508 0.8612 0.056 Uiso calc R 1 H
C12 0.9225(2) -0.03287(16) 0.80545(8) 0.0395(5) Uani d . 1 C
C3 0.8728(2) -0.06068(17) 0.70161(8) 0.0453(5) Uani d . 1 C
H3 0.7647 -0.0983 0.7038 0.068 Uiso calc R 1 H
C4 0.9601(3) -0.09268(18) 0.64337(9) 0.0534(6) Uani d . 1 C
H4A 0.9305 -0.1673 0.6315 0.080 Uiso calc R 1 H
H4B 1.0802 -0.0883 0.6480 0.080 Uiso calc R 1 H
C5 0.8988(3) -0.00911(19) 0.59674(9) 0.0556(6) Uani d . 1 C
H5B 0.9864 0.0079 0.5680 0.083 Uiso calc R 1 H
H5A 0.8034 -0.0381 0.5750 0.083 Uiso calc R 1 H
C1 0.8508(3) 0.09268(18) 0.63198(9) 0.0495(5) Uani d . 1 C
C2 0.8450(2) 0.06155(17) 0.69612(8) 0.0425(5) Uani d . 1 C
C6 0.8298(3) 0.12407(17) 0.74495(8) 0.0457(5) Uani d . 1 C
H6 0.8056 0.1990 0.7417 0.055 Uiso calc R 1 H
C7 0.8518(2) 0.07284(16) 0.80374(8) 0.0396(5) Uani d . 1 C
C8 0.8151(2) 0.12659(16) 0.85788(8) 0.0437(5) Uani d . 1 C
H8 0.7664 0.1964 0.8572 0.052 Uiso calc R 1 H
C13 0.7415(3) 0.2265(2) 0.97015(10) 0.0670(7) Uani d . 1 C
H13A 0.8094 0.2796 0.9494 0.100 Uiso calc R 1 H
H13B 0.7280 0.2488 1.0114 0.100 Uiso calc R 1 H
H13C 0.6341 0.2223 0.9511 0.100 Uiso calc R 1 H
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
_geom_angle_publ_flag
O1 C1 C2 125.9(2) y
O1 C1 C5 126.6(2) y
O2 C3 C2 112.01(15) y
O2 C3 C4 112.31(16) y
O2 C12 C11 117.81(17) y
O2 C12 C7 121.95(15) y
O3 C9 C10 115.54(16) y
O3 C9 C8 124.93(19) y
C1 C2 C3 109.02(16) ?
C1 C5 C4 105.78(17) y
C2 C1 C5 107.44(18) ?
C2 C3 C4 104.51(16) ?
C2 C6 C7 118.53(19) y
C3 C4 C5 104.98(16) y
C6 C2 C1 130.22(19) y
C6 C2 C3 120.62(17) y
C8 C7 C6 123.12(18) y
C8 C7 C12 119.19(16) ?
C9 O3 C13 118.00(15) ?
C9 C8 C7 120.30(19) ?
C10 C9 C8 119.53(18) ?
C11 C10 C9 120.81(17) ?
C12 O2 C3 114.53(14) y
C12 C7 C6 117.58(16) y
C11 C10 H10 119.6 ?
C9 C10 H10 119.6 ?
C10 C11 C12 120.11(18) ?
C10 C11 H11 119.9 ?
C12 C11 H11 119.9 ?
C11 C12 C7 120.04(17) ?
O2 C3 H3 109.3 ?
C2 C3 H3 109.3 ?
C4 C3 H3 109.3 ?
C3 C4 H4A 110.8 ?
C5 C4 H4A 110.8 ?
C3 C4 H4B 110.8 ?
C5 C4 H4B 110.8 ?
H4A C4 H4B 108.8 ?
C1 C5 H5B 110.6 ?
C4 C5 H5B 110.6 ?
C1 C5 H5A 110.6 ?
C4 C5 H5A 110.6 ?
H5B C5 H5A 108.7 ?
C2 C6 H6 120.7 ?
C7 C6 H6 120.7 ?
C9 C8 H8 119.9 ?
C7 C8 H8 119.9 ?
O3 C13 H13A 109.5 ?
O3 C13 H13B 109.5 ?
H13A C13 H13B 109.5 ?
O3 C13 H13C 109.5 ?
H13A C13 H13C 109.5 ?
H13B C13 H13C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 1.214(2) y
O2 C3 1.427(2) y
O2 C12 1.379(2) y
O3 C9 1.370(2) y
O3 C13 1.414(3) y
C1 C2 1.472(3) y
C2 C6 1.326(3) y
C3 C2 1.500(3) y
C3 C4 1.519(3) y
C4 C5 1.527(3) y
C5 C1 1.508(3) y
C6 C7 1.454(2) y
C7 C8 1.397(3) ?
C9 C8 1.385(3) ?
C9 C10 1.385(3) ?
C10 C11 1.376(3) ?
C11 C12 1.381(3) ?
C12 C7 1.399(3) ?
C3 H3 0.98 ?
C4 H4A 0.97 ?
C4 H4B 0.97 ?
C5 H5B 0.97 ?
C5 H5A 0.97 ?
C6 H6 0.93 ?
C8 H8 0.93 ?
C10 H10 0.93 ?
C11 H11 0.93 ?
C13 H13A 0.96 ?
C13 H13B 0.96 ?
C13 H13C 0.96 ?
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
_geom_hbond_publ_flag
C3 H3 O2 6_557 0.98 2.56 3.404(2) 145 y
C11 H11 O1 3_746 0.93 2.48 3.384(3) 165 y
C13 H13B O1 7_566 0.96 2.49 3.382(3) 155 y
C4 H4B Cg 6_556 0.98 2.81 3.700(3) 153 y
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
C13 O3 C9 C10 -178.85(19)
C13 O3 C9 C8 1.3(3)
O3 C9 C10 C11 179.30(18)
C8 C9 C10 C11 -0.9(3)
C9 C10 C11 C12 -0.2(3)
C3 O2 C12 C11 155.77(16)
C3 O2 C12 C7 -29.4(2)
C10 C11 C12 O2 176.70(16)
C10 C11 C12 C7 1.7(3)
C12 O2 C3 C2 44.1(2)
C12 O2 C3 C4 161.39(16)
O2 C3 C4 C5 -150.39(16)
C2 C3 C4 C5 -28.8(2)
C3 C4 C5 C1 25.9(2)
C4 C5 C1 O1 166.3(2)
C4 C5 C1 C2 -12.9(2)
O1 C1 C2 C6 -8.8(4)
C5 C1 C2 C6 170.4(2)
O1 C1 C2 C3 175.5(2)
C5 C1 C2 C3 -5.3(2)
O2 C3 C2 C6 -33.0(3)
C4 C3 C2 C6 -154.83(19)
O2 C3 C2 C1 143.20(16)
C4 C3 C2 C1 21.4(2)
C1 C2 C6 C7 -171.20(18)
C3 C2 C6 C7 4.1(3)
O2 C12 C7 C8 -176.88(17)
C11 C12 C7 C8 -2.1(3)
O2 C12 C7 C6 -0.6(3)
C11 C12 C7 C6 174.15(17)
C2 C6 C7 C8 -170.41(18)
C2 C6 C7 C12 13.5(3)
O3 C9 C8 C7 -179.74(18)
C10 C9 C8 C7 0.4(3)
C12 C7 C8 C9 1.0(3)
C6 C7 C8 C9 -175.02(17)
