#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:43:23 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178478 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/99/4029968.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_4029968
loop_
_publ_author_name
'Kim, JungKeun'
'Shokova, Elvira'
'Tafeenko, Victor'
'Kovalev, Vladimir'
_publ_section_title
;
 (CF3CO)2O/CF3SO3H-mediated synthesis of 1,3-diketones from carboxylic
 acids and aromatic ketones.
;
_journal_name_full               'Beilstein journal of organic chemistry'
_journal_page_first              2270
_journal_page_last               2278
_journal_paper_doi               10.3762/bjoc.10.236
_journal_volume                  10
_journal_year                    2014
_chemical_formula_sum            'C12 H14 Cl N O2'
_chemical_formula_weight         239.69
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_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                 90.798(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.8720(2)
_cell_length_b                   22.4177(4)
_cell_length_c                   7.7044(2)
_cell_measurement_reflns_used    7834
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70
_cell_measurement_theta_min      4
_cell_volume                     1186.78(5)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295
_diffrn_detector                 Pilatus100K
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.928
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54086
_diffrn_reflns_av_R_equivalents  0.0827
_diffrn_reflns_av_sigmaI/netI    0.0777
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3787
_diffrn_reflns_theta_full        70.03
_diffrn_reflns_theta_max         70.03
_diffrn_reflns_theta_min         3.94
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    2.733
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             504
_exptl_crystal_size_max          .17
_exptl_crystal_size_mid          .12
_exptl_crystal_size_min          .06
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       0.0089(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.875
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2100
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.875
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0507
_refine_ls_shift/su_max          0.186
_refine_ls_shift/su_mean         0.019
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0701P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1203
_refine_ls_wR_factor_ref         0.1283
_reflns_number_gt                1343
_reflns_number_total             2100
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1860-5397-10-236-S4.cif
_cod_data_source_block           sk
_cod_depositor_comments
'Adding full bibliography for 4029967--4029970.cif.'
_cod_database_code               4029968
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
Cl1 Cl 1.41111(12) 0.82589(3) 1.48582(11) 0.0686(3) Uani 1 1 d
O1 O 0.4973(3) 0.88790(10) 1.0248(3) 0.0606(6) Uani 1 1 d
N1 N 1.0273(3) 0.86091(10) 1.2712(3) 0.0538(6) Uani 1 1 d
C2 C 0.8989(5) 0.80953(15) 1.2528(6) 0.0741(10) Uani 1 1 d
C3 C 0.7513(5) 0.81711(14) 1.1099(5) 0.0642(8) Uani 1 1 d
C4 C 0.6656(4) 0.87845(12) 1.1021(3) 0.0478(6) Uani 1 1 d
C5 C 0.7376(4) 0.99059(12) 1.1488(4) 0.0469(6) Uani 1 1 d
C6 C 0.9771(4) 1.07534(12) 1.2421(4) 0.0536(7) Uani 1 1 d
C7 C 1.1567(5) 1.08801(14) 1.3171(4) 0.0562(7) Uani 1 1 d
C8 C 1.2815(4) 1.04319(13) 1.3706(3) 0.0533(7) Uani 1 1 d
C9 C 1.2326(4) 0.98407(14) 1.3506(3) 0.0504(7) Uani 1 1 d
C10 C 1.0513(4) 0.97089(11) 1.2749(3) 0.0422(6) Uani 1 1 d
C11 C 0.9230(4) 1.01607(11) 1.2220(3) 0.0430(6) Uani 1 1 d
C12 C 0.9586(4) 0.91395(11) 1.2406(3) 0.0440(6) Uani 1 1 d
C13 C 0.7713(4) 0.92463(12) 1.1643(3) 0.0446(6) Uani 1 1 d
O9 O 0.3166(4) 0.80207(11) 0.8737(3) 0.0779(7) Uani 1 1 d
H1N H 1.132(5) 0.8531(16) 1.332(4) 0.079(11) Uiso 1 1 d
H2 H 0.986(7) 0.778(2) 1.220(5) 0.119(14) Uiso 1 1 d
H21 H 0.829(8) 0.806(2) 1.397(8) 0.17(2) Uiso 1 1 d
H3 H 0.659(5) 0.7858(17) 1.111(4) 0.082(10) Uiso 1 1 d
H31 H 0.796(5) 0.8115(13) 0.995(4) 0.068(9) Uiso 1 1 d
H5 H 0.715(4) 1.0053(12) 1.023(4) 0.056(8) Uiso 1 1 d
H6 H 0.889(4) 1.1026(13) 1.201(3) 0.054(8) Uiso 1 1 d
H7 H 1.183(4) 1.1273(14) 1.333(3) 0.053(8) Uiso 1 1 d
H8 H 1.406(4) 1.0526(13) 1.420(4) 0.060(8) Uiso 1 1 d
H9 H 1.316(4) 0.9521(14) 1.396(4) 0.065(9) Uiso 1 1 d
H1O H 0.435(6) 0.854(2) 0.969(5) 0.106(13) Uiso 1 1 d
H51 H 0.630(4) 1.0029(13) 1.224(4) 0.068(9) Uiso 1 1 d
H91 H 0.341(6) 0.7582(19) 0.901(5) 0.108(13) Uiso 1 1 d
H92 H 0.354(7) 0.804(3) 0.733(8) 0.17(2) Uiso 1 1 d
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'
N N 0.0311 0.0180 '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
C12 N1 C2 119.2(3)
N1 C2 C3 112.7(3)
C2 C3 C4 113.3(3)
O1 C4 C13 120.3(2)
O1 C4 C3 120.7(2)
C13 C4 C3 118.7(3)
C11 C5 C13 102.5(2)
C7 C6 C11 118.6(3)
C8 C7 C6 121.4(3)
C9 C8 C7 121.2(3)
C8 C9 C10 117.7(3)
C11 C10 C9 121.5(2)
C11 C10 C12 108.1(2)
C9 C10 C12 130.4(2)
C6 C11 C10 119.6(3)
C6 C11 C5 129.2(2)
C10 C11 C5 111.2(2)
N1 C12 C13 123.4(2)
N1 C12 C10 128.0(3)
C13 C12 C10 108.6(2)
C4 C13 C12 119.7(2)
C4 C13 C5 130.2(2)
C12 C13 C5 109.6(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C4 1.311(3)
N1 C12 1.300(3)
N1 C2 1.457(4)
C2 C3 1.496(5)
C3 C4 1.497(4)
C4 C13 1.349(4)
C5 C11 1.499(4)
C5 C13 1.501(4)
C6 C7 1.385(4)
C6 C11 1.388(4)
C7 C8 1.380(4)
C8 C9 1.376(4)
C9 C10 1.400(4)
C10 C11 1.399(4)
C10 C12 1.449(4)
C12 C13 1.427(3)
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
C12 N1 C2 C3 34.2(5)
N1 C2 C3 C4 -41.2(5)
C2 C3 C4 O1 -158.7(3)
C2 C3 C4 C13 26.4(5)
C11 C6 C7 C8 0.3(4)
C6 C7 C8 C9 0.3(4)
C7 C8 C9 C10 -0.3(4)
C8 C9 C10 C11 -0.4(4)
C8 C9 C10 C12 -178.6(2)
C7 C6 C11 C10 -1.0(4)
C7 C6 C11 C5 178.7(3)
C9 C10 C11 C6 1.0(4)
C12 C10 C11 C6 179.6(2)
C9 C10 C11 C5 -178.8(2)
C12 C10 C11 C5 -0.2(3)
C13 C5 C11 C6 -179.8(3)
C13 C5 C11 C10 -0.1(3)
C2 N1 C12 C13 -9.8(4)
C2 N1 C12 C10 170.2(3)
C11 C10 C12 N1 -179.6(3)
C9 C10 C12 N1 -1.2(4)
C11 C10 C12 C13 0.4(3)
C9 C10 C12 C13 178.8(2)
O1 C4 C13 C12 -177.0(2)
C3 C4 C13 C12 -2.0(4)
O1 C4 C13 C5 -5.7(4)
C3 C4 C13 C5 169.2(3)
N1 C12 C13 C4 -7.6(4)
C10 C12 C13 C4 172.4(2)
N1 C12 C13 C5 179.5(2)
C10 C12 C13 C5 -0.5(3)
C11 C5 C13 C4 -171.5(3)
C11 C5 C13 C12 0.4(3)
