#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/91/2219119.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_2219119
loop_
_publ_author_name
'Gowda, B. Thimme'
'Foro, Sabine'
'Babitha, K. S.'
'Fuess, Hartmut'
_publ_section_title
;
 3-Chlorophenyl benzoate
;
_journal_coeditor_code           NG2472
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1587
_journal_paper_doi               10.1107/S1600536808022721
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C13 H9 Cl O2'
_chemical_formula_moiety         'C13 H9 Cl O2'
_chemical_formula_sum            'C13 H9 Cl O2'
_chemical_formula_weight         232.65
_chemical_name_systematic
;
3-Chlorophenyl benzoate
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                107.890(10)
_cell_angle_beta                 102.980(10)
_cell_angle_gamma                93.250(10)
_cell_formula_units_Z            2
_cell_length_a                   6.0734(6)
_cell_length_b                   8.3890(10)
_cell_length_c                   11.747(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      31.69
_cell_measurement_theta_min      5.58
_cell_volume                     549.89(13)
_computing_cell_refinement       'CAD-4-PC (Enraf--Nonius, 1996)'
_computing_data_collection       'CAD-4-PC (Enraf--Nonius, 1996)'
_computing_data_reduction        'REDU4 (Stoe & Cie, 1987)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      299(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0856
_diffrn_reflns_av_sigmaI/netI    0.0194
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2143
_diffrn_reflns_theta_full        66.93
_diffrn_reflns_theta_max         66.93
_diffrn_reflns_theta_min         4.09
_diffrn_standards_decay_%        1.0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.918
_exptl_absorpt_correction_T_max  0.2327
_exptl_absorpt_correction_T_min  0.1968
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.50
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.342
_refine_ls_extinction_coef       0.149(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1947
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0460
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0771P)²+0.1623P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1347
_reflns_number_gt                1872
_reflns_number_total             1947
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng2472.cif
_cod_data_source_block           I
_cod_database_code               2219119
_cod_database_fobs_code          2219119
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
Cl Cl1 0.29134(10) 0.17688(7) -0.06457(6) 0.0678(3) Uani d . 1
O O1 0.2384(2) 0.74790(18) 0.23750(15) 0.0565(4) Uani d . 1
O O2 0.5777(2) 0.70473(19) 0.33852(15) 0.0587(4) Uani d . 1
C C1 0.1614(3) 0.5746(2) 0.18489(18) 0.0474(5) Uani d . 1
C C2 0.2647(3) 0.4730(2) 0.10218(19) 0.0477(5) Uani d . 1
H H2 0.3962 0.5149 0.0869 0.057 Uiso calc R 1
C C3 0.1670(3) 0.3070(3) 0.04263(19) 0.0482(5) Uani d . 1
C C4 -0.0281(3) 0.2436(3) 0.0636(2) 0.0546(5) Uani d . 1
H H4 -0.0937 0.1321 0.0212 0.065 Uiso calc R 1
C C5 -0.1247(4) 0.3482(3) 0.1485(2) 0.0593(6) Uani d . 1
H H5 -0.2549 0.3060 0.1647 0.071 Uiso calc R 1
C C6 -0.0314(3) 0.5149(3) 0.2099(2) 0.0555(5) Uani d . 1
H H6 -0.0977 0.5853 0.2669 0.067 Uiso calc R 1
C C7 0.4554(3) 0.7994(3) 0.30835(17) 0.0458(5) Uani d . 1
C C8 0.5176(3) 0.9840(3) 0.34208(17) 0.0457(5) Uani d . 1
C C9 0.3622(4) 1.0902(3) 0.3149(2) 0.0568(5) Uani d . 1
H H9 0.2109 1.0464 0.2740 0.068 Uiso calc R 1
C C10 0.4331(5) 1.2610(3) 0.3487(2) 0.0680(7) Uani d . 1
H H10 0.3287 1.3323 0.3307 0.082 Uiso calc R 1
C C11 0.6556(5) 1.3268(3) 0.4086(2) 0.0692(7) Uani d . 1
H H11 0.7018 1.4423 0.4315 0.083 Uiso calc R 1
C C12 0.8107(5) 1.2214(3) 0.4347(2) 0.0717(7) Uani d . 1
H H12 0.9619 1.2658 0.4752 0.086 Uiso calc R 1
C C13 0.7428(4) 1.0512(3) 0.4013(2) 0.0602(6) Uani d . 1
H H13 0.8486 0.9804 0.4184 0.072 Uiso calc R 1
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
Cl1 0.0704(4) 0.0528(4) 0.0800(5) 0.0084(3) 0.0358(3) 0.0095(3)
O1 0.0472(8) 0.0453(8) 0.0692(9) 0.0134(6) 0.0057(6) 0.0131(7)
O2 0.0543(8) 0.0553(9) 0.0681(10) 0.0198(7) 0.0096(7) 0.0247(7)
C1 0.0436(9) 0.0457(11) 0.0534(11) 0.0114(8) 0.0092(8) 0.0183(9)
C2 0.0429(10) 0.0475(11) 0.0581(11) 0.0066(8) 0.0177(8) 0.0215(9)
C3 0.0471(10) 0.0478(11) 0.0560(11) 0.0098(8) 0.0179(8) 0.0218(9)
C4 0.0502(11) 0.0492(11) 0.0667(13) 0.0021(8) 0.0140(9) 0.0241(10)
C5 0.0447(11) 0.0721(15) 0.0711(14) 0.0048(9) 0.0210(9) 0.0335(12)
C6 0.0464(10) 0.0671(14) 0.0574(12) 0.0162(9) 0.0192(9) 0.0211(10)
C7 0.0452(10) 0.0506(11) 0.0456(10) 0.0152(8) 0.0148(8) 0.0176(8)
C8 0.0498(10) 0.0493(11) 0.0412(9) 0.0133(8) 0.0146(8) 0.0161(8)
C9 0.0574(12) 0.0549(13) 0.0593(12) 0.0174(9) 0.0124(9) 0.0202(10)
C10 0.0885(17) 0.0525(13) 0.0701(15) 0.0255(12) 0.0225(12) 0.0254(11)
C11 0.0935(18) 0.0520(13) 0.0634(14) 0.0038(12) 0.0272(12) 0.0169(11)
C12 0.0675(15) 0.0653(15) 0.0712(15) -0.0050(11) 0.0129(11) 0.0128(12)
C13 0.0534(12) 0.0594(13) 0.0630(13) 0.0109(10) 0.0076(9) 0.0177(11)
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'
Cl Cl 0.3639 0.7018 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C7 O1 C1 118.81(14)
C2 C1 C6 122.04(19)
C2 C1 O1 120.12(18)
C6 C1 O1 117.55(18)
C1 C2 C3 117.83(17)
C1 C2 H2 121.1
C3 C2 H2 121.1
C4 C3 C2 121.76(19)
C4 C3 Cl1 119.48(17)
C2 C3 Cl1 118.73(14)
C3 C4 C5 118.8(2)
C3 C4 H4 120.6
C5 C4 H4 120.6
C4 C5 C6 120.99(19)
C4 C5 H5 119.5
C6 C5 H5 119.5
C1 C6 C5 118.6(2)
C1 C6 H6 120.7
C5 C6 H6 120.7
O2 C7 O1 123.08(19)
O2 C7 C8 125.42(19)
O1 C7 C8 111.50(15)
C13 C8 C9 119.3(2)
C13 C8 C7 117.74(18)
C9 C8 C7 122.95(18)
C10 C9 C8 119.6(2)
C10 C9 H9 120.2
C8 C9 H9 120.2
C11 C10 C9 120.7(2)
C11 C10 H10 119.7
C9 C10 H10 119.7
C10 C11 C12 119.8(2)
C10 C11 H11 120.1
C12 C11 H11 120.1
C13 C12 C11 120.2(2)
C13 C12 H12 119.9
C11 C12 H12 119.9
C12 C13 C8 120.4(2)
C12 C13 H13 119.8
C8 C13 H13 119.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C3 1.739(2)
O1 C7 1.356(2)
O1 C1 1.399(2)
O2 C7 1.195(2)
C1 C2 1.374(3)
C1 C6 1.374(3)
C2 C3 1.380(3)
C2 H2 0.9300
C3 C4 1.374(3)
C4 C5 1.376(3)
C4 H4 0.9300
C5 C6 1.379(3)
C5 H5 0.9300
C6 H6 0.9300
C7 C8 1.479(3)
C8 C13 1.384(3)
C8 C9 1.387(3)
C9 C10 1.378(3)
C9 H9 0.9300
C10 C11 1.370(4)
C10 H10 0.9300
C11 C12 1.376(4)
C11 H11 0.9300
C12 C13 1.371(4)
C12 H12 0.9300
C13 H13 0.9300
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
C6 H6 O2 1_455 0.93 2.46 3.319(3) 153.7
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
C7 O1 C1 C2 -61.9(2)
C7 O1 C1 C6 124.2(2)
C6 C1 C2 C3 0.7(3)
O1 C1 C2 C3 -172.97(16)
C1 C2 C3 C4 0.5(3)
C1 C2 C3 Cl1 178.84(14)
C2 C3 C4 C5 -1.5(3)
Cl1 C3 C4 C5 -179.86(16)
C3 C4 C5 C6 1.4(3)
C2 C1 C6 C5 -0.8(3)
O1 C1 C6 C5 173.01(18)
C4 C5 C6 C1 -0.3(3)
C1 O1 C7 O2 -7.8(3)
C1 O1 C7 C8 172.24(16)
O2 C7 C8 C13 7.9(3)
O1 C7 C8 C13 -172.14(18)
O2 C7 C8 C9 -173.4(2)
O1 C7 C8 C9 6.6(3)
C13 C8 C9 C10 -1.0(3)
C7 C8 C9 C10 -179.7(2)
C8 C9 C10 C11 0.2(4)
C9 C10 C11 C12 0.4(4)
C10 C11 C12 C13 -0.2(4)
C11 C12 C13 C8 -0.6(4)
C9 C8 C13 C12 1.2(3)
C7 C8 C13 C12 180.0(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 227077
