#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/48/2204828.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_2204828
loop_
_publ_author_name
'Burcu Arslan'
'Canan Kazak'
'Hakan Göker'
_publ_section_title
;
 2,6-Dimethyl-4H-1-benzopyran-4-one
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2238
_journal_page_last               o2240
_journal_paper_doi               10.1107/S1600536804027989
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C11 H10 O2'
_chemical_formula_moiety         'C11 H10 O2'
_chemical_formula_sum            'C11 H10 O2'
_chemical_formula_weight         174.19
_chemical_name_systematic
;
2,6-Dimethyl-4H-1-benzopyran-4-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 93.979(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.4595(5)
_cell_length_b                   10.1947(14)
_cell_length_c                   15.8862(15)
_cell_measurement_reflns_used    7949
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4
_cell_measurement_theta_min      2.3
_cell_volume                     882.06(17)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Stoe IPDS-2'
_diffrn_measurement_method       'rotation method'
_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  0.088
_diffrn_reflns_av_sigmaI/netI    0.054
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6705
_diffrn_reflns_theta_full        26.0
_diffrn_reflns_theta_max         26.0
_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    0.09
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.35
_refine_diff_density_min         -0.24
_refine_ls_extinction_coef       0.093(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.11
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         1740
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.11
_refine_ls_R_factor_all          0.066
_refine_ls_R_factor_gt           0.054
_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)+(0.1083P)²+0.0774P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.175
_refine_ls_wR_factor_ref         0.184
_reflns_number_gt                1328
_reflns_number_total             1740
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ya6220.cif
_cod_data_source_block           III
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2204828
_cod_database_fobs_code          2204828
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
O1 -0.2543(2) 0.52505(13) 0.10857(8) 0.0511(4) Uani d . 1 O
O2 0.3617(3) 0.68843(16) 0.22357(9) 0.0697(5) Uani d . 1 O
C1 -0.3200(4) 0.3829(2) 0.22073(15) 0.0607(6) Uani d D 1 C
H1A -0.4548 0.3637 0.1806 0.091 Uiso calc RD 1 H
H1B -0.3821 0.4130 0.2724 0.091 Uiso calc RD 1 H
H1C -0.2240 0.3050 0.2315 0.091 Uiso calc RD 1 H
C2 -0.1652(3) 0.48550(19) 0.18658(11) 0.0485(5) Uani d . 1 C
C3 0.0386(3) 0.5368(2) 0.22472(12) 0.0511(5) Uani d . 1 C
H3 0.085(4) 0.507(2) 0.2785(15) 0.068(6) Uiso d . 1 H
C4 0.1773(3) 0.63785(19) 0.18847(11) 0.0485(5) Uani d . 1 C
C4A 0.0809(3) 0.67825(17) 0.10306(10) 0.0444(5) Uani d . 1 C
C5 0.1959(4) 0.77291(19) 0.05643(12) 0.0513(5) Uani d . 1 C
H5 0.335(5) 0.811(2) 0.0815(15) 0.067(7) Uiso d . 1 H
C6 0.1052(4) 0.80816(19) -0.02364(12) 0.0533(5) Uani d . 1 C
C7 -0.1065(4) 0.7456(2) -0.05750(12) 0.0571(6) Uani d . 1 C
H7 -0.171(5) 0.773(2) -0.1161(17) 0.076(7) Uiso d . 1 H
C8 -0.2242(4) 0.6526(2) -0.01345(12) 0.0550(5) Uani d . 1 C
H8 -0.373(4) 0.609(2) -0.0343(15) 0.064(6) Uiso d . 1 H
C9 -0.1297(3) 0.61906(18) 0.06751(11) 0.0451(5) Uani d . 1 C
C10 0.2281(5) 0.9122(2) -0.07349(15) 0.0726(7) Uani d D 1 C
H10A 0.1391 0.9232 -0.1273 0.109 Uiso calc RD 1 H
H10B 0.3936 0.8860 -0.0818 0.109 Uiso calc RD 1 H
H10C 0.2299 0.9936 -0.0431 0.109 Uiso calc RD 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0468(7) 0.0604(8) 0.0450(8) -0.0031(6) -0.0054(5) -0.0018(6)
O2 0.0646(9) 0.0890(12) 0.0526(9) -0.0150(8) -0.0163(7) -0.0062(7)
C1 0.0567(11) 0.0621(12) 0.0636(13) 0.0009(9) 0.0070(9) 0.0046(10)
C2 0.0485(10) 0.0529(10) 0.0439(10) 0.0103(8) 0.0015(7) -0.0033(8)
C3 0.0512(11) 0.0620(12) 0.0392(10) 0.0070(8) -0.0028(8) -0.0013(8)
C4 0.0467(10) 0.0589(11) 0.0387(9) 0.0040(8) -0.0048(7) -0.0102(8)
C4A 0.0463(10) 0.0497(10) 0.0367(9) 0.0053(7) 0.0000(7) -0.0100(7)
C5 0.0519(11) 0.0553(11) 0.0464(10) -0.0002(9) 0.0018(8) -0.0098(8)
C6 0.0599(12) 0.0558(11) 0.0448(10) 0.0089(9) 0.0096(8) -0.0035(8)
C7 0.0611(12) 0.0680(13) 0.0414(10) 0.0121(10) -0.0016(8) -0.0012(9)
C8 0.0508(11) 0.0694(13) 0.0434(10) 0.0011(9) -0.0084(8) -0.0045(9)
C9 0.0434(9) 0.0520(10) 0.0393(9) 0.0049(7) -0.0012(7) -0.0071(7)
C10 0.0918(17) 0.0669(14) 0.0604(13) 0.0009(12) 0.0145(12) 0.0069(10)
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
C2 O1 C9 118.97(14)
C3 C2 O1 122.06(18)
C3 C2 C1 126.33(18)
O1 C2 C1 111.61(16)
C2 C3 C4 123.32(18)
C2 C3 H3 117.2(15)
C4 C3 H3 119.4(15)
O2 C4 C3 124.17(17)
O2 C4 C4A 121.80(19)
C3 C4 C4A 114.03(16)
C9 C4A C5 118.53(17)
C9 C4A C4 119.04(17)
C5 C4A C4 122.42(17)
O1 C9 C4A 122.53(16)
O1 C9 C8 116.61(16)
C4A C9 C8 120.86(18)
C7 C8 C9 119.09(18)
C7 C8 H8 124.2(14)
C9 C8 H8 116.7(14)
C8 C7 C6 121.79(18)
C8 C7 H7 121.2(14)
C6 C7 H7 117.0(14)
C5 C6 C7 118.08(19)
C5 C6 C10 121.5(2)
C7 C6 C10 120.39(19)
C6 C5 C4A 121.65(19)
C6 C5 H5 121.4(15)
C4A C5 H5 117.0(15)
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
C6 C10 H10A 109.5
C6 C10 H10B 109.5
H10A C10 H10B 109.5
C6 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.361(2)
O1 C9 1.367(2)
O2 C4 1.230(2)
C2 C3 1.336(3)
C2 C1 1.472(3)
C3 C4 1.424(3)
C3 H3 0.93(2)
C4 C4A 1.479(2)
C4A C9 1.384(3)
C4A C5 1.392(3)
C9 C8 1.395(3)
C8 C7 1.365(3)
C8 H8 0.96(2)
C7 C6 1.395(3)
C7 H7 1.01(3)
C6 C5 1.380(3)
C6 C10 1.509(3)
C5 H5 0.92(3)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
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
C9 O1 C2 C3 0.8(3)
C9 O1 C2 C1 -179.22(14)
O1 C2 C3 C4 1.2(3)
C1 C2 C3 C4 -178.82(17)
C2 C3 C4 O2 178.10(19)
C2 C3 C4 C4A -2.1(3)
O2 C4 C4A C9 -178.97(17)
C3 C4 C4A C9 1.2(2)
O2 C4 C4A C5 1.8(3)
C3 C4 C4A C5 -178.03(16)
C2 O1 C9 C4A -1.6(2)
C2 O1 C9 C8 177.81(16)
C5 C4A C9 O1 179.86(15)
C4 C4A C9 O1 0.6(3)
C5 C4A C9 C8 0.4(3)
C4 C4A C9 C8 -178.86(16)
O1 C9 C8 C7 -179.71(16)
C4A C9 C8 C7 -0.2(3)
C9 C8 C7 C6 -0.2(3)
C8 C7 C6 C5 0.5(3)
C8 C7 C6 C10 -178.89(18)
C7 C6 C5 C4A -0.3(3)
C10 C6 C5 C4A 179.07(17)
C9 C4A C5 C6 -0.2(3)
C4 C4A C5 C6 179.11(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 589569
