#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/34/2223469.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_2223469
loop_
_publ_author_name
'Xu, Cui-Lian'
'Liu, Shan-Yu'
'Chen, Gang'
'Yang, Guo-Yu'
'Zhao, Ming-Qin'
_publ_section_title
;
 Menthyl 2-oxo-2H-chromene-3-carboxylate
;
_journal_coeditor_code           LH2883
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2431
_journal_paper_doi               10.1107/S1600536809035995
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C20 H24 O4'
_chemical_formula_moiety         'C20 H24 O4'
_chemical_formula_sum            'C20 H24 O4'
_chemical_formula_weight         328.39
_chemical_name_systematic
;
Menthyl 2-oxo-2H-chromene-3-carboxylate
;
_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'
_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            4
_cell_length_a                   11.080(2)
_cell_length_b                   12.408(3)
_cell_length_c                   13.532(3)
_cell_measurement_reflns_used    489
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      25.50
_cell_measurement_theta_min      2.23
_cell_volume                     1860.4(7)
_computing_cell_refinement       'R-AXIS (Rigaku, 1997)'
_computing_data_collection       'R-AXIS (Rigaku, 1997)'
_computing_data_reduction        'R-AXIS (Rigaku, 1997)'
_computing_molecular_graphics
;
TEXSAN (Molecular Structure Corporation & Rigaku (2000) and PLATON
(Spek,
2009)
;
_computing_publication_material
'TEXSAN (Molecular Structure Corporation & Rigaku (2000)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      291(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Rigaku R-AXIS-IV'
_diffrn_measurement_method       'Oscillation  frames'
_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  0.0631
_diffrn_reflns_av_sigmaI/netI    0.0490
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5812
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.23
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9864
_exptl_absorpt_correction_T_min  0.9856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi,1995)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.173
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.173
_refine_ls_extinction_coef       0.025(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         1943
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0565
_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)+(0.0742P)²+0.1720P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1295
_refine_ls_wR_factor_ref         0.1376
_reflns_number_gt                1654
_reflns_number_total             1943
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2883.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 'Orthorhombic' changed to
'orthorhombic' 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_cell_volume        1860.3(6)
_cod_database_code               2223469
_cod_database_fobs_code          2223469
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'
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 1.1789(2) 1.01848(18) 0.10921(18) 0.0682(7) Uani d . 1 . .
O O2 1.0992(3) 1.1284(2) 0.2180(2) 0.0863(8) Uani d . 1 . .
O O3 0.9734(2) 1.0101(2) 0.37733(18) 0.0852(8) Uani d . 1 . .
O O4 0.83141(18) 0.92908(18) 0.28562(15) 0.0591(6) Uani d . 1 . .
C C1 1.1825(3) 0.9219(3) 0.0601(2) 0.0593(8) Uani d . 1 . .
C C2 1.2617(3) 0.9135(3) -0.0176(3) 0.0814(11) Uani d . 1 . .
H H2A 1.3124 0.9706 -0.0337 0.098 Uiso calc R 1 . .
C C3 1.2651(4) 0.8204(4) -0.0710(3) 0.0929(13) Uani d . 1 . .
H H3A 1.3179 0.8145 -0.1242 0.111 Uiso calc R 1 . .
C C4 1.1909(5) 0.7341(4) -0.0468(3) 0.0931(14) Uani d . 1 . .
H H4A 1.1947 0.6707 -0.0833 0.112 Uiso calc R 1 . .
C C5 1.1114(4) 0.7426(3) 0.0315(3) 0.0760(10) Uani d . 1 . .
H H5A 1.0618 0.6849 0.0478 0.091 Uiso calc R 1 . .
C C6 1.1055(3) 0.8379(2) 0.0861(2) 0.0545(7) Uani d . 1 . .
C C7 1.0247(3) 0.8555(2) 0.1674(2) 0.0547(7) Uani d . 1 . .
H H7A 0.9738 0.8000 0.1873 0.066 Uiso calc R 1 . .
C C8 1.0208(3) 0.9499(2) 0.2151(2) 0.0508(7) Uani d . 1 . .
C C9 1.0994(3) 1.0387(3) 0.1849(2) 0.0611(8) Uani d . 1 . .
C C10 0.9412(3) 0.9684(3) 0.3017(2) 0.0571(8) Uani d . 1 . .
C C11 0.7426(3) 0.9362(2) 0.3663(2) 0.0565(8) Uani d . 1 . .
H H11A 0.7545 1.0039 0.4022 0.068 Uiso calc R 1 . .
C C12 0.6189(3) 0.9375(3) 0.3173(2) 0.0656(9) Uani d . 1 . .
H H12A 0.6123 0.8708 0.2789 0.079 Uiso calc R 1 . .
C C13 0.5222(3) 0.9316(3) 0.3989(3) 0.0834(11) Uani d . 1 . .
H H13A 0.5242 0.9976 0.4373 0.100 Uiso calc R 1 . .
H H13B 0.4431 0.9261 0.3685 0.100 Uiso calc R 1 . .
C C14 0.5413(4) 0.8365(3) 0.4669(3) 0.0853(12) Uani d . 1 . .
H H14A 0.4794 0.8369 0.5175 0.102 Uiso calc R 1 . .
H H14B 0.5327 0.7704 0.4293 0.102 Uiso calc R 1 . .
C C15 0.6634(4) 0.8376(3) 0.5156(3) 0.0755(10) Uani d . 1 . .
H H15A 0.6690 0.9033 0.5555 0.091 Uiso calc R 1 . .
C C16 0.7619(3) 0.8429(3) 0.4359(3) 0.0668(9) Uani d . 1 . .
H H16A 0.8401 0.8502 0.4675 0.080 Uiso calc R 1 . .
H H16B 0.7620 0.7761 0.3986 0.080 Uiso calc R 1 . .
C C17 0.5998(4) 1.0313(4) 0.2444(3) 0.0888(12) Uani d . 1 . .
H H17A 0.6684 1.0305 0.1987 0.107 Uiso calc R 1 . .
C C18 0.4854(5) 1.0146(6) 0.1819(4) 0.142(2) Uani d . 1 . .
H H18A 0.4882 0.9450 0.1511 0.213 Uiso calc R 1 . .
H H18B 0.4811 1.0694 0.1320 0.213 Uiso calc R 1 . .
H H18C 0.4156 1.0190 0.2237 0.213 Uiso calc R 1 . .
C C19 0.5982(5) 1.1416(4) 0.2928(4) 0.1272(19) Uani d . 1 . .
H H19A 0.5862 1.1959 0.2432 0.191 Uiso calc R 1 . .
H H19B 0.6737 1.1539 0.3257 0.191 Uiso calc R 1 . .
H H19C 0.5336 1.1447 0.3400 0.191 Uiso calc R 1 . .
C C20 0.6831(6) 0.7415(4) 0.5839(4) 0.1226(19) Uani d . 1 . .
H H20A 0.6209 0.7401 0.6332 0.184 Uiso calc R 1 . .
H H20B 0.7604 0.7479 0.6154 0.184 Uiso calc R 1 . .
H H20C 0.6805 0.6761 0.5461 0.184 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 0.0000 '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 0.0000 '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
C1 O1 C9 . . 122.7(2) ?
C10 O4 C11 . . 117.9(2) ?
O1 C1 C2 . . 117.1(3) ?
O1 C1 C6 . . 120.9(3) ?
C2 C1 C6 . . 121.9(3) ?
C3 C2 C1 . . 119.2(4) ?
C3 C2 H2A . . 120.4 ?
C1 C2 H2A . . 120.4 ?
C2 C3 C4 . . 120.8(4) ?
C2 C3 H3A . . 119.6 ?
C4 C3 H3A . . 119.6 ?
C5 C4 C3 . . 119.9(4) ?
C5 C4 H4A . . 120.1 ?
C3 C4 H4A . . 120.1 ?
C4 C5 C6 . . 120.1(4) ?
C4 C5 H5A . . 120.0 ?
C6 C5 H5A . . 120.0 ?
C1 C6 C5 . . 118.1(3) ?
C1 C6 C7 . . 117.6(3) ?
C5 C6 C7 . . 124.3(3) ?
C8 C7 C6 . . 121.5(3) ?
C8 C7 H7A . . 119.2 ?
C6 C7 H7A . . 119.2 ?
C7 C8 C9 . . 120.4(3) ?
C7 C8 C10 . . 122.4(3) ?
C9 C8 C10 . . 117.2(3) ?
O2 C9 O1 . . 116.6(3) ?
O2 C9 C8 . . 126.4(3) ?
O1 C9 C8 . . 116.9(3) ?
O3 C10 O4 . . 124.8(3) ?
O3 C10 C8 . . 124.3(3) ?
O4 C10 C8 . . 110.9(3) ?
O4 C11 C16 . . 108.8(2) ?
O4 C11 C12 . . 106.2(2) ?
C16 C11 C12 . . 114.1(3) ?
O4 C11 H11A . . 109.2 ?
C16 C11 H11A . . 109.2 ?
C12 C11 H11A . . 109.2 ?
C11 C12 C17 . . 114.3(3) ?
C11 C12 C13 . . 108.3(3) ?
C17 C12 C13 . . 113.6(3) ?
C11 C12 H12A . . 106.7 ?
C17 C12 H12A . . 106.7 ?
C13 C12 H12A . . 106.7 ?
C14 C13 C12 . . 112.1(3) ?
C14 C13 H13A . . 109.2 ?
C12 C13 H13A . . 109.2 ?
C14 C13 H13B . . 109.2 ?
C12 C13 H13B . . 109.2 ?
H13A C13 H13B . . 107.9 ?
C15 C14 C13 . . 112.6(3) ?
C15 C14 H14A . . 109.1 ?
C13 C14 H14A . . 109.1 ?
C15 C14 H14B . . 109.1 ?
C13 C14 H14B . . 109.1 ?
H14A C14 H14B . . 107.8 ?
C14 C15 C20 . . 112.8(4) ?
C14 C15 C16 . . 109.4(3) ?
C20 C15 C16 . . 110.9(4) ?
C14 C15 H15A . . 107.9 ?
C20 C15 H15A . . 107.9 ?
C16 C15 H15A . . 107.9 ?
C11 C16 C15 . . 111.7(3) ?
C11 C16 H16A . . 109.3 ?
C15 C16 H16A . . 109.3 ?
C11 C16 H16B . . 109.3 ?
C15 C16 H16B . . 109.3 ?
H16A C16 H16B . . 107.9 ?
C19 C17 C18 . . 110.4(4) ?
C19 C17 C12 . . 114.0(4) ?
C18 C17 C12 . . 111.3(4) ?
C19 C17 H17A . . 106.9 ?
C18 C17 H17A . . 106.9 ?
C12 C17 H17A . . 106.9 ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C17 C19 H19A . . 109.5 ?
C17 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C17 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C15 C20 H20A . . 109.5 ?
C15 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C15 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 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 C1 . 1.370(4) ?
O1 C9 . 1.374(4) ?
O2 C9 . 1.199(4) ?
O3 C10 . 1.201(4) ?
O4 C10 . 1.328(4) ?
O4 C11 . 1.472(4) ?
C1 C2 . 1.374(5) ?
C1 C6 . 1.392(4) ?
C2 C3 . 1.363(6) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.389(6) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.382(5) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.396(5) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.434(4) ?
C7 C8 . 1.338(4) ?
C7 H7A . 0.9300 ?
C8 C9 . 1.463(4) ?
C8 C10 . 1.485(4) ?
C11 C16 . 1.508(5) ?
C11 C12 . 1.522(4) ?
C11 H11A . 0.9800 ?
C12 C17 . 1.539(5) ?
C12 C13 . 1.540(5) ?
C12 H12A . 0.9800 ?
C13 C14 . 1.512(6) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 C15 . 1.504(6) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 C20 . 1.525(6) ?
C15 C16 . 1.535(5) ?
C15 H15A . 0.9800 ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 C19 . 1.517(7) ?
C17 C18 . 1.537(7) ?
C17 H17A . 0.9800 ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
C19 H19A . 0.9600 ?
C19 H19B . 0.9600 ?
C19 H19C . 0.9600 ?
C20 H20A . 0.9600 ?
C20 H20B . 0.9600 ?
C20 H20C . 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
_geom_hbond_publ_flag
C3 H3A O2 2_774 0.93 2.43 3.288(5) 154 y
C5 H5A O3 3_745 0.93 2.42 3.276(5) 152 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9 O1 C1 C2 . . . . 176.7(3) ?
C9 O1 C1 C6 . . . . -1.0(4) ?
O1 C1 C2 C3 . . . . -177.6(3) ?
C6 C1 C2 C3 . . . . 0.1(5) ?
C1 C2 C3 C4 . . . . -0.8(6) ?
C2 C3 C4 C5 . . . . 0.7(7) ?
C3 C4 C5 C6 . . . . 0.1(6) ?
O1 C1 C6 C5 . . . . 178.3(3) ?
C2 C1 C6 C5 . . . . 0.7(5) ?
O1 C1 C6 C7 . . . . -1.3(4) ?
C2 C1 C6 C7 . . . . -178.9(3) ?
C4 C5 C6 C1 . . . . -0.8(5) ?
C4 C5 C6 C7 . . . . 178.8(3) ?
C1 C6 C7 C8 . . . . 1.6(4) ?
C5 C6 C7 C8 . . . . -178.0(3) ?
C6 C7 C8 C9 . . . . 0.3(4) ?
C6 C7 C8 C10 . . . . -177.6(3) ?
C1 O1 C9 O2 . . . . -175.3(3) ?
C1 O1 C9 C8 . . . . 2.9(4) ?
C7 C8 C9 O2 . . . . 175.4(3) ?
C10 C8 C9 O2 . . . . -6.6(5) ?
C7 C8 C9 O1 . . . . -2.5(4) ?
C10 C8 C9 O1 . . . . 175.5(2) ?
C11 O4 C10 O3 . . . . -0.5(5) ?
C11 O4 C10 C8 . . . . 177.2(2) ?
C7 C8 C10 O3 . . . . 133.2(4) ?
C9 C8 C10 O3 . . . . -44.8(5) ?
C7 C8 C10 O4 . . . . -44.5(4) ?
C9 C8 C10 O4 . . . . 137.5(3) ?
C10 O4 C11 C16 . . . . -83.0(3) ?
C10 O4 C11 C12 . . . . 153.7(3) ?
O4 C11 C12 C17 . . . . -58.8(4) ?
C16 C11 C12 C17 . . . . -178.7(3) ?
O4 C11 C12 C13 . . . . 173.5(3) ?
C16 C11 C12 C13 . . . . 53.6(4) ?
C11 C12 C13 C14 . . . . -53.9(4) ?
C17 C12 C13 C14 . . . . 178.0(3) ?
C12 C13 C14 C15 . . . . 57.7(4) ?
C13 C14 C15 C20 . . . . -179.8(3) ?
C13 C14 C15 C16 . . . . -55.8(4) ?
O4 C11 C16 C15 . . . . -173.5(3) ?
C12 C11 C16 C15 . . . . -55.1(4) ?
C14 C15 C16 C11 . . . . 53.8(4) ?
C20 C15 C16 C11 . . . . 178.8(4) ?
C11 C12 C17 C19 . . . . -66.3(5) ?
C13 C12 C17 C19 . . . . 58.5(5) ?
C11 C12 C17 C18 . . . . 167.9(4) ?
C13 C12 C17 C18 . . . . -67.2(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24743275
