#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/15/2221525.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_2221525
loop_
_publ_author_name
'Zonouzi, Afsaneh'
'Biniaz, Mojtaba'
'Rahmani, Hossein'
'Ng, Seik Weng'
_publ_section_title
;
 1-(2-Ethoxy-2-methyl-2H-chromen-3-yl)ethanone
;
_journal_coeditor_code           TK2390
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o752
_journal_paper_doi               10.1107/S1600536809008502
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H16 O3'
_chemical_formula_moiety         'C14 H16 O3'
_chemical_formula_sum            'C14 H16 O3'
_chemical_formula_weight         232.27
_chemical_name_systematic
;
1-(2-Ethoxy-2-methyl-2H-chromen-3-yl)ethanone
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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
_cell_angle_beta                 123.2940(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.0084(5)
_cell_length_b                   7.2637(2)
_cell_length_c                   19.1056(5)
_cell_measurement_reflns_used    2233
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      28.1
_cell_measurement_theta_min      2.4
_cell_volume                     2320.96(11)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART APEX'
_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  0.035
_diffrn_reflns_av_sigmaI/netI    0.044
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            7793
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.4
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Irregular block'
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.429
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2655
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.03
_refine_ls_R_factor_all          0.060
_refine_ls_R_factor_gt           0.047
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0739P)²+1.4605P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.129
_refine_ls_wR_factor_ref         0.140
_reflns_number_gt                2123
_reflns_number_total             2655
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2390.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2221525
_cod_database_fobs_code          2221525
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x, y, -z-1/2'
'-x+1/2, -y+1/2, -z'
'-x+1/2, 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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.13572(6) 0.55707(15) 0.32959(6) 0.0208(3) Uani d . 1 . .
O O2 0.17621(6) 0.25748(14) 0.32719(6) 0.0211(3) Uani d . 1 . .
O O3 0.36134(7) 0.35871(19) 0.38669(7) 0.0350(3) Uani d . 1 . .
C C1 0.19962(9) 0.4438(2) 0.33800(9) 0.0193(3) Uani d . 1 . .
C C2 0.27375(9) 0.4496(2) 0.42713(9) 0.0189(3) Uani d . 1 . .
C C3 0.26440(9) 0.4851(2) 0.49036(9) 0.0198(3) Uani d . 1 . .
H H3 0.3098 0.4792 0.5463 0.024 Uiso calc R 1 . .
C C4 0.18788(9) 0.5318(2) 0.47624(9) 0.0190(3) Uani d . 1 . .
C C5 0.17449(9) 0.5519(2) 0.54044(9) 0.0223(3) Uani d . 1 . .
H H5 0.2169 0.5303 0.5969 0.027 Uiso calc R 1 . .
C C6 0.10015(10) 0.6026(2) 0.52253(10) 0.0244(3) Uani d . 1 . .
H H6 0.0917 0.6164 0.5666 0.029 Uiso calc R 1 . .
C C7 0.03757(10) 0.6336(2) 0.43999(10) 0.0239(3) Uani d . 1 . .
H H7 -0.0135 0.6686 0.4280 0.029 Uiso calc R 1 . .
C C8 0.04917(9) 0.6137(2) 0.37524(9) 0.0222(3) Uani d . 1 . .
H H8 0.0063 0.6340 0.3189 0.027 Uiso calc R 1 . .
C C9 0.12413(9) 0.5638(2) 0.39363(9) 0.0185(3) Uani d . 1 . .
C C10 0.20936(10) 0.5212(2) 0.27015(9) 0.0250(4) Uani d . 1 . .
H H10A 0.1566 0.5384 0.2185 0.037 Uiso calc R 1 . .
H H10B 0.2407 0.4352 0.2597 0.037 Uiso calc R 1 . .
H H10C 0.2371 0.6399 0.2885 0.037 Uiso calc R 1 . .
C C11 0.11063(10) 0.2021(2) 0.24546(9) 0.0282(4) Uani d . 1 . .
H H11A 0.1250 0.2167 0.2037 0.034 Uiso calc R 1 . .
H H11B 0.0628 0.2781 0.2278 0.034 Uiso calc R 1 . .
C C12 0.09445(12) 0.0053(3) 0.25244(12) 0.0409(5) Uani d . 1 . .
H H12A 0.0504 -0.0390 0.1978 0.061 Uiso calc R 1 . .
H H12B 0.0798 -0.0068 0.2935 0.061 Uiso calc R 1 . .
H H12C 0.1425 -0.0678 0.2706 0.061 Uiso calc R 1 . .
C C13 0.35266(9) 0.3964(2) 0.44326(9) 0.0218(3) Uani d . 1 . .
C C14 0.42348(9) 0.3868(2) 0.53284(9) 0.0256(4) Uani d . 1 . .
H H14A 0.4721 0.3623 0.5337 0.038 Uiso calc R 1 . .
H H14B 0.4152 0.2876 0.5621 0.038 Uiso calc R 1 . .
H H14C 0.4291 0.5043 0.5608 0.038 Uiso calc R 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 O1 C1 . . 119.55(11) ?
C1 O2 C11 . . 117.31(11) ?
O2 C1 O1 . . 109.01(12) ?
O2 C1 C10 . . 114.69(12) ?
O1 C1 C10 . . 102.32(11) ?
O2 C1 C2 . . 103.36(11) ?
O1 C1 C2 . . 111.41(11) ?
C10 C1 C2 . . 116.12(13) ?
C3 C2 C13 . . 121.33(13) ?
C3 C2 C1 . . 118.58(13) ?
C13 C2 C1 . . 119.74(13) ?
C2 C3 C4 . . 122.28(13) ?
C2 C3 H3 . . 118.9 ?
C4 C3 H3 . . 118.9 ?
C5 C4 C9 . . 118.45(14) ?
C5 C4 C3 . . 123.72(13) ?
C9 C4 C3 . . 117.81(13) ?
C6 C5 C4 . . 120.60(14) ?
C6 C5 H5 . . 119.7 ?
C4 C5 H5 . . 119.7 ?
C5 C6 C7 . . 120.05(14) ?
C5 C6 H6 . . 120.0 ?
C7 C6 H6 . . 120.0 ?
C8 C7 C6 . . 120.47(14) ?
C8 C7 H7 . . 119.8 ?
C6 C7 H7 . . 119.8 ?
C7 C8 C9 . . 119.25(14) ?
C7 C8 H8 . . 120.4 ?
C9 C8 H8 . . 120.4 ?
O1 C9 C8 . . 118.29(13) ?
O1 C9 C4 . . 120.41(13) ?
C8 C9 C4 . . 121.18(13) ?
C1 C10 H10A . . 109.5 ?
C1 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C1 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
O2 C11 C12 . . 106.55(13) ?
O2 C11 H11A . . 110.4 ?
C12 C11 H11A . . 110.4 ?
O2 C11 H11B . . 110.4 ?
C12 C11 H11B . . 110.4 ?
H11A C11 H11B . . 108.6 ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
O3 C13 C2 . . 121.91(13) ?
O3 C13 C14 . . 119.59(14) ?
C2 C13 C14 . . 118.49(13) ?
C13 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C13 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C9 . 1.3654(17) ?
O1 C1 . 1.4531(18) ?
O2 C1 . 1.4101(18) ?
O2 C11 . 1.4397(17) ?
O3 C13 . 1.2164(18) ?
C1 C10 . 1.520(2) ?
C1 C2 . 1.5259(19) ?
C2 C3 . 1.345(2) ?
C2 C13 . 1.484(2) ?
C3 C4 . 1.442(2) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.400(2) ?
C4 C9 . 1.4006(19) ?
C5 C6 . 1.381(2) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.392(2) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.386(2) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.388(2) ?
C8 H8 . 0.9500 ?
C10 H10A . 0.9800 ?
C10 H10B . 0.9800 ?
C10 H10C . 0.9800 ?
C11 C12 . 1.488(3) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 H12A . 0.9800 ?
C12 H12B . 0.9800 ?
C12 H12C . 0.9800 ?
C13 C14 . 1.510(2) ?
C14 H14A . 0.9800 ?
C14 H14B . 0.9800 ?
C14 H14C . 0.9800 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C11 O2 C1 O1 . . . . 66.57(15) ?
C11 O2 C1 C10 . . . . -47.43(18) ?
C11 O2 C1 C2 . . . . -174.83(12) ?
C9 O1 C1 O2 . . . . 75.85(15) ?
C9 O1 C1 C10 . . . . -162.31(12) ?
C9 O1 C1 C2 . . . . -37.58(17) ?
O2 C1 C2 C3 . . . . -90.42(15) ?
O1 C1 C2 C3 . . . . 26.51(19) ?
C10 C1 C2 C3 . . . . 143.09(15) ?
O2 C1 C2 C13 . . . . 82.91(16) ?
O1 C1 C2 C13 . . . . -160.17(13) ?
C10 C1 C2 C13 . . . . -43.59(19) ?
C13 C2 C3 C4 . . . . -178.17(14) ?
C1 C2 C3 C4 . . . . -5.0(2) ?
C2 C3 C4 C5 . . . . 173.50(14) ?
C2 C3 C4 C9 . . . . -8.3(2) ?
C9 C4 C5 C6 . . . . -0.2(2) ?
C3 C4 C5 C6 . . . . 177.92(15) ?
C4 C5 C6 C7 . . . . 0.3(2) ?
C5 C6 C7 C8 . . . . 0.1(2) ?
C6 C7 C8 C9 . . . . -0.5(2) ?
C1 O1 C9 C8 . . . . -157.01(13) ?
C1 O1 C9 C4 . . . . 26.77(19) ?
C7 C8 C9 O1 . . . . -175.65(13) ?
C7 C8 C9 C4 . . . . 0.5(2) ?
C5 C4 C9 O1 . . . . 175.92(13) ?
C3 C4 C9 O1 . . . . -2.3(2) ?
C5 C4 C9 C8 . . . . -0.2(2) ?
C3 C4 C9 C8 . . . . -178.45(14) ?
C1 O2 C11 C12 . . . . -176.06(14) ?
C3 C2 C13 O3 . . . . 177.78(15) ?
C1 C2 C13 O3 . . . . 4.6(2) ?
C3 C2 C13 C14 . . . . -1.4(2) ?
C1 C2 C13 C14 . . . . -174.50(13) ?
