#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/08/2230890.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_2230890
loop_
_publ_author_name
'Gowda, Ramakrishna'
'Gowda, K.V. Arjuna'
'Basanagouda, Mahantesha'
'Kulkarni, Manohar V.'
_publ_section_title
;
 6-Chloro-4-(4-methylphenoxymethyl)-2H-chromen-2-one
;
_journal_coeditor_code           VM2090
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1650
_journal_paper_doi               10.1107/S1600536811019258
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C17 H13 Cl O3'
_chemical_formula_moiety         'C17 H13 Cl O3'
_chemical_formula_sum            'C17 H13 Cl O3'
_chemical_formula_weight         300.72
_chemical_name_systematic
;
6-Chloro-4-(4-methylphenoxymethyl)-2H-chromen-2-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                90.00
_cell_angle_beta                 116.923(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.3068(5)
_cell_length_b                   6.9353(2)
_cell_length_c                   14.9566(5)
_cell_measurement_reflns_used    4071
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      2.7
_cell_volume                     1415.66(8)
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT and XPREP (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'ω and φ'
_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  0.0378
_diffrn_reflns_av_sigmaI/netI    0.0338
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16899
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.16
_diffrn_reflns_theta_min         1.49
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.277
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_correction_T_min  0.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.216
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3818
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0928
_refine_ls_R_factor_gt           0.0533
_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)+(0.0833P)²+0.2177P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1387
_refine_ls_wR_factor_ref         0.1698
_reflns_number_gt                2448
_reflns_number_total             3818
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            vm2090.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2230890
_cod_database_fobs_code          2230890
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.09025(16) 0.1827(4) 0.68708(19) 0.0627(7) Uani d . 1 1 . .
H H1 0.0528 0.1718 0.7215 0.075 Uiso calc R 1 1 . .
C C2 0.04581(17) 0.2170(4) 0.5863(2) 0.0652(7) Uani d . 1 1 . .
H H2 -0.0219 0.2299 0.5514 0.078 Uiso calc R 1 1 . .
C C3 0.10297(15) 0.2323(4) 0.53657(16) 0.0509(5) Uani d . 1 1 . .
C C4 0.20280(14) 0.2106(3) 0.58555(15) 0.0430(5) Uani d . 1 1 . .
H H4 0.2395 0.2191 0.5503 0.052 Uiso calc R 1 1 . .
C C5 0.24892(13) 0.1756(3) 0.68853(14) 0.0371(4) Uani d . 1 1 . .
C C6 0.19059(15) 0.1644(3) 0.73768(16) 0.0448(5) Uani d . 1 1 . .
C C7 0.35374(13) 0.1530(3) 0.74835(14) 0.0359(4) Uani d . 1 1 . .
C C8 0.39041(14) 0.1275(3) 0.84735(15) 0.0428(5) Uani d . 1 1 . .
H H8 0.4578 0.1139 0.8853 0.051 Uiso calc R 1 1 . .
C C9 0.32906(15) 0.1204(3) 0.89761(16) 0.0482(5) Uani d . 1 1 . .
C C10 0.41673(12) 0.1566(3) 0.69576(14) 0.0384(4) Uani d . 1 1 . .
H H10A 0.4010 0.0477 0.6503 0.046 Uiso calc R 1 1 . .
H H10B 0.4049 0.2741 0.6568 0.046 Uiso calc R 1 1 . .
C C11 0.58438(13) 0.1494(3) 0.73188(15) 0.0380(4) Uani d . 1 1 . .
C C12 0.56245(14) 0.1461(3) 0.63200(15) 0.0437(5) Uani d . 1 1 . .
H H12 0.4976 0.1427 0.5829 0.052 Uiso calc R 1 1 . .
C C13 0.63822(15) 0.1481(3) 0.60532(17) 0.0488(5) Uani d . 1 1 . .
H H13 0.6233 0.1448 0.5377 0.059 Uiso calc R 1 1 . .
C C14 0.73516(15) 0.1549(3) 0.67619(18) 0.0505(5) Uani d . 1 1 . .
C C15 0.75450(15) 0.1587(3) 0.77520(19) 0.0525(6) Uani d . 1 1 . .
H H15 0.8193 0.1637 0.8243 0.063 Uiso calc R 1 1 . .
C C16 0.68085(14) 0.1553(3) 0.80433(16) 0.0458(5) Uani d . 1 1 . .
H H16 0.6960 0.1571 0.8720 0.055 Uiso calc R 1 1 . .
C C17 0.81634(18) 0.1592(4) 0.6449(2) 0.0747(8) Uani d . 1 1 . .
H H17A 0.8295 0.2904 0.6344 0.112 Uiso calc R 1 1 . .
H H17B 0.7965 0.0876 0.5839 0.112 Uiso calc R 1 1 . .
H H17C 0.8745 0.1026 0.6967 0.112 Uiso calc R 1 1 . .
O O1 0.23009(10) 0.1370(2) 0.83898(11) 0.0524(4) Uani d . 1 1 . .
O O2 0.35626(12) 0.1007(3) 0.98589(11) 0.0684(5) Uani d . 1 1 . .
O O3 0.51603(9) 0.1474(2) 0.76774(10) 0.0459(4) Uani d . 1 1 . .
Cl Cl1 0.04586(4) 0.28400(13) 0.40961(5) 0.0790(3) Uani d . 1 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'
Cl Cl 0.1484 0.1585 '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
C2 C1 C6 . . 119.81(19) ?
C2 C1 H1 . . 120.1 ?
C6 C1 H1 . . 120.1 ?
C1 C2 C3 . . 119.1(2) ?
C1 C2 H2 . . 120.5 ?
C3 C2 H2 . . 120.5 ?
C4 C3 C2 . . 121.8(2) ?
C4 C3 Cl1 . . 119.73(16) ?
C2 C3 Cl1 . . 118.47(17) ?
C3 C4 C5 . . 119.56(18) ?
C3 C4 H4 . . 120.2 ?
C5 C4 H4 . . 120.2 ?
C6 C5 C4 . . 117.91(17) ?
C6 C5 C7 . . 117.61(18) ?
C4 C5 C7 . . 124.48(16) ?
O1 C6 C1 . . 116.47(17) ?
O1 C6 C5 . . 121.71(18) ?
C1 C6 C5 . . 121.8(2) ?
C8 C7 C5 . . 119.38(16) ?
C8 C7 C10 . . 122.52(17) ?
C5 C7 C10 . . 118.09(16) ?
C7 C8 C9 . . 122.34(18) ?
C7 C8 H8 . . 118.8 ?
C9 C8 H8 . . 118.8 ?
O2 C9 O1 . . 116.54(18) ?
O2 C9 C8 . . 126.4(2) ?
O1 C9 C8 . . 117.07(17) ?
O3 C10 C7 . . 109.05(15) ?
O3 C10 H10A . . 109.9 ?
C7 C10 H10A . . 109.9 ?
O3 C10 H10B . . 109.9 ?
C7 C10 H10B . . 109.9 ?
H10A C10 H10B . . 108.3 ?
O3 C11 C12 . . 124.69(16) ?
O3 C11 C16 . . 115.23(17) ?
C12 C11 C16 . . 120.08(17) ?
C11 C12 C13 . . 119.20(18) ?
C11 C12 H12 . . 120.4 ?
C13 C12 H12 . . 120.4 ?
C14 C13 C12 . . 121.9(2) ?
C14 C13 H13 . . 119.1 ?
C12 C13 H13 . . 119.1 ?
C15 C14 C13 . . 117.46(18) ?
C15 C14 C17 . . 121.8(2) ?
C13 C14 C17 . . 120.7(2) ?
C14 C15 C16 . . 122.1(2) ?
C14 C15 H15 . . 118.9 ?
C16 C15 H15 . . 118.9 ?
C15 C16 C11 . . 119.2(2) ?
C15 C16 H16 . . 120.4 ?
C11 C16 H16 . . 120.4 ?
C14 C17 H17A . . 109.5 ?
C14 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C14 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C6 O1 C9 . . 121.85(15) ?
C11 O3 C10 . . 116.67(14) ?
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
C1 C2 . 1.365(3) ?
C1 C6 . 1.377(3) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.385(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.371(3) ?
C3 Cl1 . 1.731(2) ?
C4 C5 . 1.394(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.392(2) ?
C5 C7 . 1.449(2) ?
C6 O1 . 1.367(2) ?
C7 C8 . 1.336(3) ?
C7 C10 . 1.495(2) ?
C8 C9 . 1.445(3) ?
C8 H8 . 0.9300 ?
C9 O2 . 1.199(2) ?
C9 O1 . 1.369(3) ?
C10 O3 . 1.411(2) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 O3 . 1.375(2) ?
C11 C12 . 1.375(3) ?
C11 C16 . 1.381(3) ?
C12 C13 . 1.387(3) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.380(3) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.373(3) ?
C14 C17 . 1.513(3) ?
C15 C16 . 1.381(3) ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 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
C10 H10B O2 4_554 0.97 2.47 3.303(5) 143 y
C4 H4 O2 4_554 0.93 2.69 3.553(4) 154 y
C1 H1 Cl1 4_555 0.93 2.88 3.693(4) 146 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
C6 C1 C2 C3 . . . . 0.1(4) ?
C1 C2 C3 C4 . . . . 1.2(4) ?
C1 C2 C3 Cl1 . . . . -177.8(2) ?
C2 C3 C4 C5 . . . . -1.2(4) ?
Cl1 C3 C4 C5 . . . . 177.74(16) ?
C3 C4 C5 C6 . . . . 0.0(3) ?
C3 C4 C5 C7 . . . . -179.1(2) ?
C2 C1 C6 O1 . . . . 177.8(2) ?
C2 C1 C6 C5 . . . . -1.4(4) ?
C4 C5 C6 O1 . . . . -177.77(18) ?
C7 C5 C6 O1 . . . . 1.4(3) ?
C4 C5 C6 C1 . . . . 1.3(3) ?
C7 C5 C6 C1 . . . . -179.5(2) ?
C6 C5 C7 C8 . . . . -1.7(3) ?
C4 C5 C7 C8 . . . . 177.35(19) ?
C6 C5 C7 C10 . . . . 177.49(17) ?
C4 C5 C7 C10 . . . . -3.4(3) ?
C5 C7 C8 C9 . . . . 0.4(3) ?
C10 C7 C8 C9 . . . . -178.76(19) ?
C7 C8 C9 O2 . . . . -178.9(2) ?
C7 C8 C9 O1 . . . . 1.3(3) ?
C8 C7 C10 O3 . . . . -5.3(3) ?
C5 C7 C10 O3 . . . . 175.47(16) ?
O3 C11 C12 C13 . . . . -179.84(19) ?
C16 C11 C12 C13 . . . . 0.3(3) ?
C11 C12 C13 C14 . . . . -0.5(3) ?
C12 C13 C14 C15 . . . . 0.3(3) ?
C12 C13 C14 C17 . . . . -179.3(2) ?
C13 C14 C15 C16 . . . . 0.2(3) ?
C17 C14 C15 C16 . . . . 179.8(2) ?
C14 C15 C16 C11 . . . . -0.5(3) ?
O3 C11 C16 C15 . . . . -179.67(19) ?
C12 C11 C16 C15 . . . . 0.2(3) ?
C1 C6 O1 C9 . . . . -178.8(2) ?
C5 C6 O1 C9 . . . . 0.4(3) ?
O2 C9 O1 C6 . . . . 178.5(2) ?
C8 C9 O1 C6 . . . . -1.7(3) ?
C12 C11 O3 C10 . . . . -4.7(3) ?
C16 C11 O3 C10 . . . . 175.20(17) ?
C7 C10 O3 C11 . . . . -179.97(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656804
