#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/73/2227346.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227346
loop_
_publ_author_name
'Jasinski, Jerry P.'
'Pek, Albert E.'
'Narayana, B.'
'Yathirajan, H. S.'
'Nayak, Prakash S.'
_publ_section_title
;
 2-(4-Chlorophenyl)-6-methoxychroman-4-one
;
_journal_coeditor_code           CV2754
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2546
_journal_page_last               o2547
_journal_paper_doi               10.1107/S1600536810035816
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C16 H13 Cl O3'
_chemical_formula_moiety         'C16 H13 Cl O3'
_chemical_formula_sum            'C16 H13 Cl O3'
_chemical_formula_weight         288.71
_chemical_name_systematic
;
2-(4-Chlorophenyl)-6-methoxychroman-4-one
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                108.035(5)
_cell_angle_beta                 98.379(4)
_cell_angle_gamma                91.820(5)
_cell_formula_units_Z            2
_cell_length_a                   5.0188(3)
_cell_length_b                   12.0138(7)
_cell_length_c                   12.3708(7)
_cell_measurement_reflns_used    2808
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.1673
_cell_measurement_theta_min      4.4902
_cell_volume                     699.33(7)
_computing_cell_refinement
'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_data_collection
'CrysAlis Pro (Oxford Diffraction, 2007)'
_computing_data_reduction
'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.5081
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type
'Oxford Diffraction Xcalibur with a Ruby (Gemini Cu) detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_av_sigmaI/netI    0.0167
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4431
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         74.33
_diffrn_reflns_theta_min         4.49
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.459
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2007)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          .40
_exptl_crystal_size_mid          .35
_exptl_crystal_size_min          .20
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.389
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.622
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2733
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.622
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0489
_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)+(0.0720P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1434
_refine_ls_wR_factor_ref         0.1556
_reflns_number_gt                2318
_reflns_number_total             2733
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cv2754.cif
_cod_data_source_block           I
_cod_database_code               2227346
_cod_database_fobs_code          2227346
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
Cl Cl1 1.44159(18) 1.09772(6) 1.41015(7) 0.1128(4) Uani d . 1 . .
C C15 0.1890(4) 0.52826(16) 0.74092(15) 0.0510(4) Uani d . 1 . .
H H14 0.1871 0.4469 0.7205 0.061 Uiso calc R 1 . .
C C10 0.3876(3) 0.59907(15) 0.82937(14) 0.0445(4) Uani d . 1 . .
C C11 0.3896(3) 0.72078(15) 0.85979(14) 0.0457(4) Uani d . 1 . .
C C5 0.8624(4) 0.83325(15) 1.12894(15) 0.0486(4) Uani d . 1 . .
C C4 1.0438(4) 0.90581(17) 1.10279(18) 0.0588(5) Uani d . 1 . .
H H4 1.0451 0.9004 1.0262 0.071 Uiso calc R 1 . .
C C3 1.2237(5) 0.98652(19) 1.1888(2) 0.0698(6) Uani d . 1 . .
H H3 1.3442 1.0356 1.1706 0.084 Uiso calc R 1 . .
C C2 1.2221(5) 0.99320(18) 1.3011(2) 0.0703(6) Uani d . 1 . .
C C6 0.8664(5) 0.8411(2) 1.24293(19) 0.0714(6) Uani d . 1 . .
H H6 0.7459 0.7924 1.2617 0.098(9) Uiso calc R 1 . .
C C1 1.0475(6) 0.9205(2) 1.3295(2) 0.0830(7) Uani d . 1 . .
H H1 1.0510 0.9247 1.4061 0.100 Uiso calc R 1 . .
C C12 0.1994(4) 0.77156(17) 0.79994(16) 0.0547(4) Uani d . 1 . .
H H11 0.2034 0.8528 0.8183 0.066 Uiso calc R 1 . .
C C14 -0.0029(4) 0.57890(18) 0.68435(16) 0.0564(5) Uani d . 1 . .
C C13 0.0067(4) 0.70101(19) 0.71392(17) 0.0610(5) Uani d . 1 . .
H H12 -0.1204 0.7352 0.6744 0.073 Uiso calc R 1 . .
C C7 0.6684(3) 0.74364(14) 1.03660(15) 0.0454(4) Uani d . 1 . .
H H7 0.5149 0.7247 1.0703 0.055 Uiso calc R 1 . .
C C9 0.5995(3) 0.54557(14) 0.88808(15) 0.0453(4) Uani d . 1 . .
C C8 0.7957(3) 0.63138(15) 0.98271(15) 0.0483(4) Uani d . 1 . .
H H8B 0.8568 0.5958 1.0415 0.058 Uiso calc R 1 . .
H H8A 0.9521 0.6497 0.9517 0.058 Uiso calc R 1 . .
O O1 0.5707(2) 0.79532(10) 0.94837(11) 0.0500(3) Uani d . 1 . .
O O2 0.6175(3) 0.43987(11) 0.86011(12) 0.0597(4) Uani d . 1 . .
O O3 -0.2094(3) 0.51981(15) 0.59887(13) 0.0759(5) Uani d . 1 . .
C C16 -0.2392(5) 0.3957(2) 0.5693(2) 0.0841(7) Uani d . 1 . .
H H15A -0.0793 0.3635 0.5425 0.126 Uiso calc R 1 . .
H H15B -0.3924 0.3652 0.5094 0.126 Uiso calc R 1 . .
H H15C -0.2661 0.3745 0.6358 0.126 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 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
C14 C15 C10 . . 120.12(17) ?
C14 C15 H14 . . 119.9 ?
C10 C15 H14 . . 119.9 ?
C11 C10 C15 . . 119.75(16) ?
C11 C10 C9 . . 119.71(15) ?
C15 C10 C9 . . 120.51(15) ?
O1 C11 C10 . . 122.90(15) ?
O1 C11 C12 . . 117.23(15) ?
C10 C11 C12 . . 119.86(16) ?
C6 C5 C4 . . 118.74(19) ?
C6 C5 C7 . . 119.48(18) ?
C4 C5 C7 . . 121.74(16) ?
C5 C4 C3 . . 120.9(2) ?
C5 C4 H4 . . 119.5 ?
C3 C4 H4 . . 119.5 ?
C2 C3 C4 . . 119.2(2) ?
C2 C3 H3 . . 120.4 ?
C4 C3 H3 . . 120.4 ?
C3 C2 C1 . . 121.2(2) ?
C3 C2 Cl1 . . 119.3(2) ?
C1 C2 Cl1 . . 119.45(19) ?
C5 C6 C1 . . 120.8(2) ?
C5 C6 H6 . . 119.6 ?
C1 C6 H6 . . 119.6 ?
C2 C1 C6 . . 119.1(2) ?
C2 C1 H1 . . 120.4 ?
C6 C1 H1 . . 120.4 ?
C13 C12 C11 . . 119.55(18) ?
C13 C12 H11 . . 120.2 ?
C11 C12 H11 . . 120.2 ?
C15 C14 O3 . . 125.69(19) ?
C15 C14 C13 . . 119.31(17) ?
O3 C14 C13 . . 115.00(18) ?
C12 C13 C14 . . 121.37(17) ?
C12 C13 H12 . . 119.3 ?
C14 C13 H12 . . 119.3 ?
O1 C7 C5 . . 108.13(13) ?
O1 C7 C8 . . 109.43(14) ?
C5 C7 C8 . . 112.84(14) ?
O1 C7 H7 . . 108.8 ?
C5 C7 H7 . . 108.8 ?
C8 C7 H7 . . 108.8 ?
O2 C9 C10 . . 122.50(16) ?
O2 C9 C8 . . 122.51(16) ?
C10 C9 C8 . . 114.97(14) ?
C7 C8 C9 . . 111.46(14) ?
C7 C8 H8B . . 109.3 ?
C9 C8 H8B . . 109.3 ?
C7 C8 H8A . . 109.3 ?
C9 C8 H8A . . 109.3 ?
H8B C8 H8A . . 108.0 ?
C11 O1 C7 . . 112.96(12) ?
C14 O3 C16 . . 117.73(18) ?
O3 C16 H15A . . 109.5 ?
O3 C16 H15B . . 109.5 ?
H15A C16 H15B . . 109.5 ?
O3 C16 H15C . . 109.5 ?
H15A C16 H15C . . 109.5 ?
H15B C16 H15C . . 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
Cl1 C2 . 1.744(2) ?
C15 C14 . 1.376(3) ?
C15 C10 . 1.402(2) ?
C15 H14 . 0.9300 ?
C10 C11 . 1.392(2) ?
C10 C9 . 1.476(2) ?
C11 O1 . 1.371(2) ?
C11 C12 . 1.393(2) ?
C5 C6 . 1.381(3) ?
C5 C4 . 1.380(3) ?
C5 C7 . 1.503(2) ?
C4 C3 . 1.383(3) ?
C4 H4 . 0.9300 ?
C3 C2 . 1.367(4) ?
C3 H3 . 0.9300 ?
C2 C1 . 1.373(4) ?
C6 C1 . 1.383(3) ?
C6 H6 . 0.9300 ?
C1 H1 . 0.9300 ?
C12 C13 . 1.370(3) ?
C12 H11 . 0.9300 ?
C14 O3 . 1.366(2) ?
C14 C13 . 1.395(3) ?
C13 H12 . 0.9300 ?
C7 O1 . 1.449(2) ?
C7 C8 . 1.515(2) ?
C7 H7 . 0.9800 ?
C9 O2 . 1.219(2) ?
C9 C8 . 1.502(2) ?
C8 H8B . 0.9700 ?
C8 H8A . 0.9700 ?
O3 C16 . 1.418(3) ?
C16 H15A . 0.9600 ?
C16 H15B . 0.9600 ?
C16 H15C . 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
C7 H7 O2 2_667 0.98 2.50 3.260(2) 134.7
C8 H8B Cg1 1_655 0.97 2.69 3.5709(18) 151
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
C14 C15 C10 C11 . . . . 0.1(3) ?
C14 C15 C10 C9 . . . . -178.06(16) ?
C15 C10 C11 O1 . . . . 177.30(15) ?
C9 C10 C11 O1 . . . . -4.6(2) ?
C15 C10 C11 C12 . . . . -1.9(3) ?
C9 C10 C11 C12 . . . . 176.21(15) ?
C6 C5 C4 C3 . . . . -1.1(3) ?
C7 C5 C4 C3 . . . . -178.99(18) ?
C5 C4 C3 C2 . . . . 0.6(3) ?
C4 C3 C2 C1 . . . . 0.7(4) ?
C4 C3 C2 Cl1 . . . . -178.13(16) ?
C4 C5 C6 C1 . . . . 0.4(3) ?
C7 C5 C6 C1 . . . . 178.3(2) ?
C3 C2 C1 C6 . . . . -1.4(4) ?
Cl1 C2 C1 C6 . . . . 177.40(19) ?
C5 C6 C1 C2 . . . . 0.9(4) ?
O1 C11 C12 C13 . . . . -177.23(17) ?
C10 C11 C12 C13 . . . . 2.0(3) ?
C10 C15 C14 O3 . . . . -178.47(18) ?
C10 C15 C14 C13 . . . . 1.6(3) ?
C11 C12 C13 C14 . . . . -0.3(3) ?
C15 C14 C13 C12 . . . . -1.5(3) ?
O3 C14 C13 C12 . . . . 178.56(19) ?
C6 C5 C7 O1 . . . . 142.77(18) ?
C4 C5 C7 O1 . . . . -39.4(2) ?
C6 C5 C7 C8 . . . . -96.0(2) ?
C4 C5 C7 C8 . . . . 81.8(2) ?
C11 C10 C9 O2 . . . . -175.33(17) ?
C15 C10 C9 O2 . . . . 2.8(3) ?
C11 C10 C9 C8 . . . . 3.1(2) ?
C15 C10 C9 C8 . . . . -178.80(15) ?
O1 C7 C8 C9 . . . . -57.54(18) ?
C5 C7 C8 C9 . . . . -177.98(14) ?
O2 C9 C8 C7 . . . . -154.04(17) ?
C10 C9 C8 C7 . . . . 27.6(2) ?
C10 C11 O1 C7 . . . . -26.7(2) ?
C12 C11 O1 C7 . . . . 152.50(16) ?
C5 C7 O1 C11 . . . . -179.56(13) ?
C8 C7 O1 C11 . . . . 57.17(18) ?
C15 C14 O3 C16 . . . . 3.6(3) ?
C13 C14 O3 C16 . . . . -176.6(2) ?
