#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2224583.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_2224583
loop_
_publ_author_name
'Jotani, Mukesh M.'
'Jasinski, Jerry P.'
'Baldaniya, Bharat B.'
'Butcher, Ray J.'
_publ_section_title
;
N-(3,4-Dichlorophenyl)-3-oxobutanamide
;
_journal_coeditor_code CI2974
_journal_issue 1
_journal_name_full 'Acta Crystallographica Section E'
_journal_page_first o58
_journal_page_last o59
_journal_volume 66
_journal_year 2010
_chemical_formula_iupac 'C10 H9 Cl2 N O2'
_chemical_formula_moiety 'C10 H9 Cl2 N O2'
_chemical_formula_sum 'C10 H9 Cl2 N O2'
_chemical_formula_weight 246.08
_chemical_name_systematic
;
N-(3,4-Dichlorophenyl)-3-oxobutanamide
;
_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
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_formula_units_Z 8
_cell_length_a 9.7171(4)
_cell_length_b 8.2834(5)
_cell_length_c 27.4857(16)
_cell_measurement_reflns_used 4228
_cell_measurement_temperature 200(2)
_cell_measurement_theta_max 32.4410
_cell_measurement_theta_min 4.8527
_cell_volume 2212.3(2)
_computing_cell_refinement
'CrysAlisRed (Oxford Diffraction, 2007)'
_computing_data_collection
'CrysAlisPro (Oxford Diffraction, 2007)'
_computing_data_reduction
'CrysAlisRed (Oxford Diffraction, 2007)'
_computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003)'
_computing_structure_refinement 'SHELXL97)(Sheldrick, 2008)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature 200(2)
_diffrn_detector_area_resol_mean 10.5081
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_device_type 'Oxford Diffraction Gemini'
_diffrn_measurement_method '\f and \w scans'
_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 0.0446
_diffrn_reflns_av_sigmaI/netI 0.0639
_diffrn_reflns_limit_h_max 14
_diffrn_reflns_limit_h_min -14
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_l_max 39
_diffrn_reflns_limit_l_min -39
_diffrn_reflns_number 16980
_diffrn_reflns_theta_full 25.00
_diffrn_reflns_theta_max 32.52
_diffrn_reflns_theta_min 4.86
_diffrn_standards_decay_% <2%
_diffrn_standards_number 0
_exptl_absorpt_coefficient_mu 0.565
_exptl_absorpt_correction_T_max 0.924
_exptl_absorpt_correction_T_min 0.725
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
(CrysAlisRed; Oxford Diffraction, 2007)
;
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.478
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description Plate
_exptl_crystal_F_000 1008
_exptl_crystal_size_max 0.56
_exptl_crystal_size_mid 0.35
_exptl_crystal_size_min 0.14
_refine_diff_density_max 0.214
_refine_diff_density_min -0.265
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.040
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 137
_refine_ls_number_reflns 3745
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.040
_refine_ls_R_factor_all 0.1224
_refine_ls_R_factor_gt 0.0476
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0532P)^2^+0.0634P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1070
_refine_ls_wR_factor_ref 0.1230
_reflns_number_gt 1910
_reflns_number_total 3745
_reflns_threshold_expression I>2\s(I)
_[local]_cod_data_source_file ci2974.cif
_[local]_cod_data_source_block I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_database_code 2224583
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
Cl Cl1 0.44746(6) 0.24662(8) 0.45002(2) 0.0723(2) Uani d . 1
Cl Cl2 0.72279(6) 0.05651(7) 0.47381(2) 0.0685(2) Uani d . 1
O O1 0.79285(11) 0.25949(19) 0.23755(5) 0.0569(4) Uani d . 1
O O2 0.64604(16) 0.07935(16) 0.15306(6) 0.0661(4) Uani d . 1
N N 0.58187(12) 0.24207(16) 0.27204(5) 0.0362(3) Uani d . 1
H H0A 0.4932 0.2505 0.2661 0.043 Uiso calc R 1
C C1 0.61935(15) 0.19559(18) 0.31946(6) 0.0335(4) Uani d . 1
C C2 0.52923(16) 0.2333(2) 0.35679(7) 0.0390(4) Uani d . 1
H H2A 0.4453 0.2872 0.3496 0.047 Uiso calc R 1
C C3 0.56032(17) 0.1931(2) 0.40451(7) 0.0429(4) Uani d . 1
C C4 0.68175(19) 0.1122(2) 0.41514(7) 0.0431(4) Uani d . 1
C C5 0.77092(18) 0.0733(2) 0.37786(7) 0.0444(4) Uani d . 1
H H5A 0.8543 0.0185 0.3851 0.053 Uiso calc R 1
C C6 0.74098(17) 0.1129(2) 0.33015(7) 0.0401(4) Uani d . 1
H H6A 0.8027 0.0840 0.3048 0.048 Uiso calc R 1
C C7 0.66728(16) 0.2750(2) 0.23478(7) 0.0382(4) Uani d . 1
C C8 0.60112(17) 0.3356(2) 0.18869(7) 0.0420(4) Uani d . 1
H H8A 0.6441 0.4395 0.1795 0.050 Uiso calc R 1
H H8B 0.5023 0.3560 0.1949 0.050 Uiso calc R 1
C C9 0.61455(17) 0.2188(2) 0.14672(7) 0.0434(4) Uani d . 1
C C10 0.5849(2) 0.2844(3) 0.09710(8) 0.0644(6) Uani d . 1
H H10A 0.5898 0.1969 0.0732 0.097 Uiso calc R 1
H H10B 0.6529 0.3675 0.0890 0.097 Uiso calc R 1
H H10C 0.4925 0.3319 0.0967 0.097 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 0.0658(4) 0.0910(5) 0.0601(3) 0.0116(3) 0.0270(3) 0.0049(3)
Cl2 0.0810(4) 0.0739(4) 0.0507(3) -0.0003(3) -0.0064(3) 0.0127(3)
O1 0.0190(6) 0.0920(11) 0.0598(8) 0.0011(6) 0.0034(5) 0.0184(8)
O2 0.0785(10) 0.0437(8) 0.0759(11) 0.0137(7) -0.0205(8) 0.0024(7)
N 0.0162(5) 0.0413(8) 0.0510(8) 0.0006(6) 0.0005(6) 0.0015(7)
C1 0.0230(7) 0.0275(8) 0.0500(10) -0.0048(6) -0.0003(7) -0.0027(7)
C2 0.0258(8) 0.0354(9) 0.0557(11) -0.0007(7) 0.0047(7) -0.0004(8)
C3 0.0395(10) 0.0379(9) 0.0514(11) -0.0054(8) 0.0113(8) 0.0002(8)
C4 0.0477(10) 0.0373(9) 0.0443(11) -0.0068(8) -0.0028(8) 0.0046(8)
C5 0.0388(9) 0.0372(10) 0.0572(12) 0.0056(8) -0.0034(9) 0.0019(9)
C6 0.0314(8) 0.0382(10) 0.0508(10) 0.0051(7) 0.0012(8) -0.0022(8)
C7 0.0232(7) 0.0385(9) 0.0530(10) -0.0001(7) 0.0013(7) 0.0031(8)
C8 0.0285(8) 0.0382(10) 0.0593(12) 0.0045(8) 0.0020(8) 0.0094(8)
C9 0.0276(8) 0.0425(11) 0.0601(12) 0.0027(8) -0.0050(8) 0.0089(9)
C10 0.0637(13) 0.0739(15) 0.0558(13) 0.0119(11) -0.0047(11) 0.0150(11)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
N N 0.0061 0.0033 '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
C7 N C1 126.91(13)
C7 N H0A 116.5
C1 N H0A 116.5
C2 C1 C6 119.32(16)
C2 C1 N 117.45(14)
C6 C1 N 123.22(15)
C1 C2 C3 120.60(15)
C1 C2 H2A 119.7
C3 C2 H2A 119.7
C2 C3 C4 120.01(16)
C2 C3 Cl1 119.13(13)
C4 C3 Cl1 120.86(15)
C5 C4 C3 119.36(17)
C5 C4 Cl2 119.13(14)
C3 C4 Cl2 121.51(15)
C4 C5 C6 121.12(16)
C4 C5 H5A 119.4
C6 C5 H5A 119.4
C5 C6 C1 119.57(16)
C5 C6 H6A 120.2
C1 C6 H6A 120.2
O1 C7 N 122.94(16)
O1 C7 C8 120.69(16)
N C7 C8 116.37(13)
C7 C8 C9 113.05(15)
C7 C8 H8A 109.0
C9 C8 H8A 109.0
C7 C8 H8B 109.0
C9 C8 H8B 109.0
H8A C8 H8B 107.8
O2 C9 C10 121.89(19)
O2 C9 C8 121.61(18)
C10 C9 C8 116.50(17)
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C3 1.7215(18)
Cl2 C4 1.7241(19)
O1 C7 1.2292(18)
O2 C9 1.207(2)
N C7 1.346(2)
N C1 1.407(2)
N H0A 0.88
C1 C2 1.385(2)
C1 C6 1.397(2)
C2 C3 1.387(3)
C2 H2A 0.95
C3 C4 1.388(3)
C4 C5 1.380(3)
C5 C6 1.383(3)
C5 H5A 0.95
C6 H6A 0.95
C7 C8 1.507(2)
C8 C9 1.511(3)
C8 H8A 0.99
C8 H8B 0.99
C9 C10 1.496(3)
C10 H10A 0.98
C10 H10B 0.98
C10 H10C 0.98
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
N H0A O1 6_556 0.88 1.95 2.824(2) 172
C6 H6A O1 . 0.95 2.35 2.865(2) 113
C2 H2A O2 3_655 0.95 2.58 3.345(2) 138
C8 H8A O2 8_765 0.99 2.45 3.327(2) 147
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 N C1 C2 152.83(15)
C7 N C1 C6 -27.9(2)
C6 C1 C2 C3 1.5(2)
N C1 C2 C3 -179.14(15)
C1 C2 C3 C4 -1.0(3)
C1 C2 C3 Cl1 178.40(13)
C2 C3 C4 C5 0.3(3)
Cl1 C3 C4 C5 -179.00(14)
C2 C3 C4 Cl2 -178.72(14)
Cl1 C3 C4 Cl2 1.9(2)
C3 C4 C5 C6 -0.3(3)
Cl2 C4 C5 C6 178.76(14)
C4 C5 C6 C1 0.9(3)
C2 C1 C6 C5 -1.5(2)
N C1 C6 C5 179.22(15)
C1 N C7 O1 3.9(3)
C1 N C7 C8 -175.10(15)
O1 C7 C8 C9 67.3(2)
N C7 C8 C9 -113.63(17)
C7 C8 C9 O2 15.9(2)
C7 C8 C9 C10 -164.88(15)