#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/44/2204404.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_2204404
loop_
_publ_author_name
'Zhang, Ying'
'Feng, Tian-Yang'
_publ_section_title
;
 2-Chloro-N-(5-chloro-4-fluoro-2-nitrophenyl)acetamide
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1717
_journal_page_last               o1718
_journal_paper_doi               10.1107/S1600536804021646
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C8 H5 Cl2 F N2 O3'
_chemical_formula_moiety         'C8 H5 Cl2 F N2 O3'
_chemical_formula_sum            'C8 H5 Cl2 F N2 O3'
_chemical_formula_weight         267.04
_chemical_name_systematic
;
2-Chloro-N-(5-chloro-4-fluoro-2-nitrophenyl)acetamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 93.139(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.193(3)
_cell_length_b                   6.4489(19)
_cell_length_c                   14.427(4)
_cell_measurement_reflns_used    860
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.16
_cell_measurement_theta_min      3.46
_cell_volume                     1039.8(5)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_sigmaI/netI    0.0275
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            5701
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         2.83
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.631
_exptl_absorpt_correction_T_max  0.881
_exptl_absorpt_correction_T_min  0.826
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.706
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.397
_refine_ls_extinction_coef       0.031(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2104
_refine_ls_number_restraints     31
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0348
_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)+(0.0468P)²+0.356P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0952
_reflns_number_gt                1618
_reflns_number_total             2104
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn6273.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2204404
_cod_database_fobs_code          2204404
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_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
_atom_site_type_symbol
Cl1 0.66307(5) 0.02654(9) -0.04980(4) 0.0540(2) Uani d . 1 A . Cl
Cl2 0.43021(6) 0.86911(12) 0.30681(5) 0.0791(3) Uani d . 1 . . Cl
F1 0.88359(12) 0.2647(2) -0.04761(10) 0.0651(4) Uani d . 1 . . F
N1 0.54229(15) 0.6038(3) 0.17069(12) 0.0420(4) Uani d D 1 A . N
H1 0.564(2) 0.713(2) 0.2000(14) 0.049(7) Uiso d D 1 . . H
N2 0.77366(18) 0.8099(3) 0.15175(13) 0.0548(5) Uani d D 1 . . N
O1 0.39531(16) 0.3590(3) 0.16375(14) 0.0745(6) Uani d . 1 A . O
O2 0.7006(6) 0.8982(14) 0.1977(6) 0.070(2) Uani d PDU 0.81(3) A 1 O
O3 0.8714(6) 0.887(2) 0.1370(9) 0.082(3) Uani d PDU 0.81(3) A 1 O
O2' 0.7082(19) 0.919(5) 0.195(2) 0.047(7) Uani d PDU 0.19(3) A 2 O
O3' 0.8826(8) 0.814(5) 0.170(2) 0.056(6) Uani d PDU 0.19(3) A 2 O
C1 0.62743(16) 0.5200(3) 0.11420(13) 0.0354(4) Uani d . 1 . . C
C2 0.73868(18) 0.6164(3) 0.10460(13) 0.0397(5) Uani d . 1 A . C
C3 0.82427(18) 0.5318(4) 0.04992(15) 0.0461(5) Uani d . 1 . . C
H3 0.8973 0.5981 0.0443 0.055 Uiso calc R 1 A . H
C4 0.80003(18) 0.3507(3) 0.00464(15) 0.0441(5) Uani d . 1 A . C
C5 0.69164(18) 0.2525(3) 0.01112(14) 0.0385(4) Uani d . 1 . . C
C6 0.60614(17) 0.3368(3) 0.06539(14) 0.0398(5) Uani d . 1 A . C
H6 0.5330 0.2699 0.0693 0.048 Uiso calc R 1 . . H
C7 0.43841(19) 0.5167(3) 0.19534(16) 0.0459(5) Uani d . 1 . . C
C8 0.3721(2) 0.6279(4) 0.26896(19) 0.0608(6) Uani d . 1 A . C
H8A 0.3697 0.5374 0.3225 0.073 Uiso calc R 1 . . H
H8B 0.2902 0.6490 0.2453 0.073 Uiso calc R 1 . . H
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'
F F 0.0171 0.0103 '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 N1 C1 127.97(18)
C7 N1 H1 115.8(16)
C1 N1 H1 115.4(16)
O2' N2 O2 8(2)
O2' N2 O3 115.0(17)
O2 N2 O3 122.2(4)
O2' N2 O3' 119.8(12)
O2 N2 O3' 123.9(10)
O3 N2 O3' 31.9(11)
O2' N2 C2 125.3(16)
O2 N2 C2 118.6(5)
O3 N2 C2 118.8(3)
O3' N2 C2 110.7(10)
C6 C1 N1 121.42(17)
C6 C1 C2 117.02(18)
N1 C1 C2 121.55(18)
C3 C2 C1 121.74(19)
C3 C2 N2 115.11(18)
C1 C2 N2 123.15(18)
C4 C3 C2 119.09(19)
C4 C3 H3 120.5
C2 C3 H3 120.5
F1 C4 C3 119.66(18)
F1 C4 C5 119.22(19)
C3 C4 C5 121.12(19)
C4 C5 C6 119.85(19)
C4 C5 Cl1 119.63(16)
C6 C5 Cl1 120.51(15)
C5 C6 C1 121.17(18)
C5 C6 H6 119.4
C1 C6 H6 119.4
O1 C7 N1 125.6(2)
O1 C7 C8 117.7(2)
N1 C7 C8 116.7(2)
C7 C8 Cl2 116.77(17)
C7 C8 H8A 108.1
Cl2 C8 H8A 108.1
C7 C8 H8B 108.1
Cl2 C8 H8B 108.1
H8A C8 H8B 107.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C5 1.722(2)
Cl2 C8 1.761(3)
F1 C4 1.352(2)
N1 C7 1.356(3)
N1 C1 1.396(3)
N1 H1 0.849(10)
N2 O2' 1.210(10)
N2 O2 1.221(4)
N2 O3 1.231(4)
N2 O3' 1.233(9)
N2 C2 1.465(3)
O1 C7 1.204(3)
C1 C6 1.389(3)
C1 C2 1.405(3)
C2 C3 1.386(3)
C3 C4 1.358(3)
C3 H3 0.9300
C4 C5 1.376(3)
C5 C6 1.381(3)
C6 H6 0.9300
C7 C8 1.510(3)
C8 H8A 0.9700
C8 H8B 0.9700
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1 Cl2 0.850(10) 2.42(2) 2.937(2) 120(2)
N1 H1 O2 0.850(10) 1.94(2) 2.611(9) 135(2)
N1 H1 O2' 0.850(10) 2.10(4) 2.766(4) 135(2)
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 N1 C1 C6 8.3(3)
C7 N1 C1 C2 -171.3(2)
C6 C1 C2 C3 -0.8(3)
N1 C1 C2 C3 178.81(19)
C6 C1 C2 N2 180.00(18)
N1 C1 C2 N2 -0.4(3)
O2' N2 C2 C3 172(2)
O2 N2 C2 C3 176.7(6)
O3 N2 C2 C3 3.1(10)
O3' N2 C2 C3 -31(2)
O2' N2 C2 C1 -9(2)
O2 N2 C2 C1 -4.1(6)
O3 N2 C2 C1 -177.6(10)
O3' N2 C2 C1 148(2)
C1 C2 C3 C4 -0.2(3)
N2 C2 C3 C4 179.09(19)
C2 C3 C4 F1 -178.83(19)
C2 C3 C4 C5 1.0(3)
F1 C4 C5 C6 178.99(18)
C3 C4 C5 C6 -0.9(3)
F1 C4 C5 Cl1 -1.8(3)
C3 C4 C5 Cl1 178.34(17)
C4 C5 C6 C1 -0.2(3)
Cl1 C5 C6 C1 -179.36(15)
N1 C1 C6 C5 -178.65(18)
C2 C1 C6 C5 1.0(3)
C1 N1 C7 O1 -8.8(4)
C1 N1 C7 C8 171.0(2)
O1 C7 C8 Cl2 -174.7(2)
N1 C7 C8 Cl2 5.5(3)
