#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/07/2230737.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_2230737
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Asik, Safra Izuani Jama'
'Garudachari, B.'
'Isloor, Arun M.'
'Satyanarayan, M. N.'
_publ_section_title
;
 2-(4-Chlorophenyl)-2-oxoethyl 2-methoxybenzoate
;
_journal_coeditor_code           IS2727
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1687
_journal_paper_doi               10.1107/S1600536811021246
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C16 H13 Cl O4'
_chemical_formula_moiety         'C16 H13 Cl O4'
_chemical_formula_sum            'C16 H13 Cl O4'
_chemical_formula_weight         304.71
_chemical_name_systematic
;
2-(4-Chlorophenyl)-2-oxoethyl 2-methoxybenzoate
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   7.7207(6)
_cell_length_b                   14.4411(12)
_cell_length_c                   26.064(2)
_cell_measurement_reflns_used    3855
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.23
_cell_measurement_theta_min      2.93
_cell_volume                     2906.0(4)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEXII DUO CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0251
_diffrn_reflns_av_sigmaI/netI    0.0215
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            16215
_diffrn_reflns_theta_full        29.49
_diffrn_reflns_theta_max         29.49
_diffrn_reflns_theta_min         2.93
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.275
_exptl_absorpt_correction_T_max  0.9495
_exptl_absorpt_correction_T_min  0.8285
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.352
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         4027
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0471P)²+0.6504P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1160
_reflns_number_gt                2731
_reflns_number_total             4027
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2727.cif
_cod_data_source_block           I
_cod_database_code               2230737
_cod_database_fobs_code          2230737
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'
'-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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 1.18791(7) 0.06652(3) 1.10182(2) 0.08142(19) Uani d . 1 1 . .
O O1 0.45975(15) 0.12921(11) 0.96747(5) 0.0746(4) Uani d . 1 1 . .
O O2 0.49777(16) 0.19520(7) 0.87365(5) 0.0624(3) Uani d . 1 1 . .
O O3 0.46624(16) 0.04491(8) 0.85569(5) 0.0667(3) Uani d . 1 1 . .
O O4 0.19233(15) 0.00492(7) 0.79740(4) 0.0600(3) Uani d . 1 1 . .
C C1 0.9263(2) 0.14336(11) 0.97782(6) 0.0523(4) Uani d . 1 1 . .
H H1A 0.9515 0.1678 0.9457 0.063 Uiso calc R 1 1 . .
C C2 1.0596(2) 0.12582(11) 1.01201(7) 0.0571(4) Uani d . 1 1 . .
H H2A 1.1739 0.1382 1.0031 0.068 Uiso calc R 1 1 . .
C C3 1.0198(2) 0.08973(10) 1.05937(6) 0.0546(4) Uani d . 1 1 . .
C C4 0.8517(2) 0.07047(11) 1.07348(7) 0.0582(4) Uani d . 1 1 . .
H H4A 0.8276 0.0459 1.1057 0.070 Uiso calc R 1 1 . .
C C5 0.7198(2) 0.08809(11) 1.03928(6) 0.0534(4) Uani d . 1 1 . .
H H5A 0.6059 0.0753 1.0485 0.064 Uiso calc R 1 1 . .
C C6 0.75479(19) 0.12480(10) 0.99111(6) 0.0455(3) Uani d . 1 1 . .
C C7 0.6086(2) 0.14152(10) 0.95508(6) 0.0504(4) Uani d . 1 1 . .
C C8 0.6513(2) 0.17422(11) 0.90174(6) 0.0543(4) Uani d . 1 1 . .
H H8A 0.7236 0.2290 0.9037 0.065 Uiso calc R 1 1 . .
H H8B 0.7159 0.1265 0.8839 0.065 Uiso calc R 1 1 . .
C C9 0.4084(2) 0.12187(10) 0.85521(5) 0.0487(3) Uani d . 1 1 . .
C C10 0.2379(2) 0.15154(10) 0.83489(5) 0.0462(3) Uani d . 1 1 . .
C C11 0.1787(2) 0.24124(11) 0.84420(6) 0.0566(4) Uani d . 1 1 . .
H H11A 0.2469 0.2813 0.8635 0.068 Uiso calc R 1 1 . .
C C12 0.0216(3) 0.27210(13) 0.82551(7) 0.0672(5) Uani d . 1 1 . .
H H12A -0.0156 0.3322 0.8321 0.081 Uiso calc R 1 1 . .
C C13 -0.0790(2) 0.21275(13) 0.79706(7) 0.0669(5) Uani d . 1 1 . .
H H13A -0.1847 0.2331 0.7842 0.080 Uiso calc R 1 1 . .
C C14 -0.0255(2) 0.12352(12) 0.78741(6) 0.0594(4) Uani d . 1 1 . .
H H14A -0.0954 0.0842 0.7682 0.071 Uiso calc R 1 1 . .
C C15 0.1320(2) 0.09184(10) 0.80609(5) 0.0475(3) Uani d . 1 1 . .
C C16 0.0868(3) -0.05690(13) 0.76827(8) 0.0822(6) Uani d . 1 1 . .
H H16A 0.1445 -0.1155 0.7650 0.123 Uiso calc R 1 1 . .
H H16B 0.0669 -0.0313 0.7348 0.123 Uiso calc R 1 1 . .
H H16C -0.0221 -0.0655 0.7854 0.123 Uiso calc R 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
C9 O2 C8 . . 116.12(12) ?
C15 O4 C16 . . 118.10(13) ?
C2 C1 C6 . . 120.70(15) ?
C2 C1 H1A . . 119.6 ?
C6 C1 H1A . . 119.6 ?
C3 C2 C1 . . 118.78(15) ?
C3 C2 H2A . . 120.6 ?
C1 C2 H2A . . 120.6 ?
C2 C3 C4 . . 121.79(15) ?
C2 C3 Cl1 . . 118.55(14) ?
C4 C3 Cl1 . . 119.66(14) ?
C3 C4 C5 . . 119.14(16) ?
C3 C4 H4A . . 120.4 ?
C5 C4 H4A . . 120.4 ?
C4 C5 C6 . . 120.75(15) ?
C4 C5 H5A . . 119.6 ?
C6 C5 H5A . . 119.6 ?
C5 C6 C1 . . 118.84(15) ?
C5 C6 C7 . . 118.98(14) ?
C1 C6 C7 . . 122.17(14) ?
O1 C7 C6 . . 121.98(15) ?
O1 C7 C8 . . 120.12(15) ?
C6 C7 C8 . . 117.90(13) ?
O2 C8 C7 . . 111.06(14) ?
O2 C8 H8A . . 109.4 ?
C7 C8 H8A . . 109.4 ?
O2 C8 H8B . . 109.4 ?
C7 C8 H8B . . 109.4 ?
H8A C8 H8B . . 108.0 ?
O3 C9 O2 . . 122.20(15) ?
O3 C9 C10 . . 127.08(14) ?
O2 C9 C10 . . 110.71(12) ?
C11 C10 C15 . . 118.16(14) ?
C11 C10 C9 . . 119.82(14) ?
C15 C10 C9 . . 122.02(13) ?
C12 C11 C10 . . 121.74(16) ?
C12 C11 H11A . . 119.1 ?
C10 C11 H11A . . 119.1 ?
C13 C12 C11 . . 119.05(16) ?
C13 C12 H12A . . 120.5 ?
C11 C12 H12A . . 120.5 ?
C12 C13 C14 . . 120.86(17) ?
C12 C13 H13A . . 119.6 ?
C14 C13 H13A . . 119.6 ?
C13 C14 C15 . . 120.51(17) ?
C13 C14 H14A . . 119.7 ?
C15 C14 H14A . . 119.7 ?
O4 C15 C14 . . 123.15(14) ?
O4 C15 C10 . . 117.17(14) ?
C14 C15 C10 . . 119.67(15) ?
O4 C16 H16A . . 109.5 ?
O4 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
O4 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 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 C3 . 1.7380(17) ?
O1 C7 . 1.2069(19) ?
O2 C9 . 1.3521(18) ?
O2 C8 . 1.426(2) ?
O3 C9 . 1.1978(18) ?
O4 C15 . 1.3579(18) ?
O4 C16 . 1.428(2) ?
C1 C2 . 1.384(2) ?
C1 C6 . 1.395(2) ?
C1 H1A . 0.9300 ?
C2 C3 . 1.375(2) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.377(3) ?
C4 C5 . 1.377(2) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.390(2) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.488(2) ?
C7 C8 . 1.505(2) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.482(2) ?
C10 C11 . 1.395(2) ?
C10 C15 . 1.406(2) ?
C11 C12 . 1.381(2) ?
C11 H11A . 0.9300 ?
C12 C13 . 1.374(3) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.376(3) ?
C13 H13A . 0.9300 ?
C14 C15 . 1.388(2) ?
C14 H14A . 0.9300 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 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
C2 H2A O1 1_655 0.9300 2.4000 3.301(2) 164.00 yes
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 . . . . 0.0(2) ?
C1 C2 C3 C4 . . . . 0.2(2) ?
C1 C2 C3 Cl1 . . . . 179.21(12) ?
C2 C3 C4 C5 . . . . -0.2(2) ?
Cl1 C3 C4 C5 . . . . -179.21(12) ?
C3 C4 C5 C6 . . . . 0.0(2) ?
C4 C5 C6 C1 . . . . 0.2(2) ?
C4 C5 C6 C7 . . . . 179.14(14) ?
C2 C1 C6 C5 . . . . -0.2(2) ?
C2 C1 C6 C7 . . . . -179.12(14) ?
C5 C6 C7 O1 . . . . 4.4(2) ?
C1 C6 C7 O1 . . . . -176.70(15) ?
C5 C6 C7 C8 . . . . -175.29(13) ?
C1 C6 C7 C8 . . . . 3.6(2) ?
C9 O2 C8 C7 . . . . -77.10(17) ?
O1 C7 C8 O2 . . . . 5.8(2) ?
C6 C7 C8 O2 . . . . -174.59(12) ?
C8 O2 C9 O3 . . . . -10.5(2) ?
C8 O2 C9 C10 . . . . 170.17(13) ?
O3 C9 C10 C11 . . . . 170.24(16) ?
O2 C9 C10 C11 . . . . -10.50(19) ?
O3 C9 C10 C15 . . . . -9.9(2) ?
O2 C9 C10 C15 . . . . 169.40(13) ?
C15 C10 C11 C12 . . . . -0.7(2) ?
C9 C10 C11 C12 . . . . 179.24(15) ?
C10 C11 C12 C13 . . . . 0.1(3) ?
C11 C12 C13 C14 . . . . 0.4(3) ?
C12 C13 C14 C15 . . . . -0.3(3) ?
C16 O4 C15 C14 . . . . -1.0(2) ?
C16 O4 C15 C10 . . . . 179.95(16) ?
C13 C14 C15 O4 . . . . -179.34(15) ?
C13 C14 C15 C10 . . . . -0.3(2) ?
C11 C10 C15 O4 . . . . 179.86(13) ?
C9 C10 C15 O4 . . . . 0.0(2) ?
C11 C10 C15 C14 . . . . 0.7(2) ?
C9 C10 C15 C14 . . . . -179.15(14) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 508679
