#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/87/2218767.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_2218767
loop_
_publ_author_name
'Mayes, Benjamin A.'
'McGarry, Patrick'
'Moussa, Adel'
'Watkin, David J.'
_publ_section_title
;
 4-Chloro-3-fluoro-2-methylaniline--pyrrolidine-2,5-dione (1/1)
;
_journal_coeditor_code           LH2642
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1355
_journal_paper_doi               10.1107/S1600536808018795
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C7 H7 Cl F N, C4 H5 N O2'
_chemical_formula_moiety         'C7 H7 Cl F N, C4 H5 N O2'
_chemical_formula_sum            'C11 H12 Cl F N2 O2'
_chemical_formula_weight         258.68
_chemical_name_systematic
;
4-Chloro-3-fluoro-2-methylaniline--pyrrolidine-2,5-dione (1/1)
;
_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
_audit_creation_method           CRYSTALS_ver_12.84
_cell_angle_alpha                73.1036(13)
_cell_angle_beta                 85.9336(12)
_cell_angle_gamma                71.3703(14)
_cell_formula_units_Z            2
_cell_length_a                   7.3853(2)
_cell_length_b                   7.4390(2)
_cell_length_c                   11.5571(4)
_cell_measurement_reflns_used    2870
_cell_measurement_temperature    120
_cell_measurement_theta_max      29
_cell_measurement_theta_min      5
_cell_volume                     575.53(3)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al.,  1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al.,  2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al.,  2003)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1994)'
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.033
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16689
_diffrn_reflns_theta_full        28.074
_diffrn_reflns_theta_max         28.647
_diffrn_reflns_theta_min         5.387
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.336
_exptl_absorpt_correction_T_max  0.87
_exptl_absorpt_correction_T_min  0.47
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(DENZO/SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.41
_refine_diff_density_max         0.38
_refine_diff_density_min         -0.37
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.8754
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2904
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0322
_refine_ls_shift/su_max          0.000819
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
Method= Modified Sheldrick  w=1/[σ²(F²) + (0.05P)² + 0.35P],
where P=[max(Fo²,0) + 2Fc²]/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0871
_refine_ls_wR_factor_gt          0.0847
_refine_ls_wR_factor_ref         0.0871
_reflns_number_gt                2610
_reflns_number_total             2904
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2642.cif
_cod_data_source_block           I
_cod_original_formula_sum        'C11 H12 Cl1 F1 N2 O2'
_cod_database_code               2218767
_cod_database_fobs_code          2218767
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_occupancy
C C11 0.94307(16) 0.30918(17) 0.66142(11) 0.0207 Uani 1.0000
N N12 0.99166(15) 0.16670(15) 0.59934(9) 0.0223 Uani 1.0000
C C13 1.10284(16) -0.01507(17) 0.66627(11) 0.0205 Uani 1.0000
C C14 1.14595(16) -0.00013(17) 0.78815(10) 0.0204 Uani 1.0000
C C15 1.04097(16) 0.21516(17) 0.78494(11) 0.0211 Uani 1.0000
O O16 1.15499(13) -0.16202(13) 0.62979(8) 0.0275 Uani 1.0000
O O17 0.83954(13) 0.47656(13) 0.62086(8) 0.0280 Uani 1.0000
H H141 1.2797 -0.0325 0.7987 0.0245 Uiso 1.0000
H H142 1.0987 -0.0916 0.8511 0.0240 Uiso 1.0000
H H151 1.1221 0.2859 0.7939 0.0258 Uiso 1.0000
H H152 0.9471 0.2271 0.8474 0.0263 Uiso 1.0000
H H1 0.9510 0.1824 0.5287 0.0265 Uiso 1.0000
C C1 0.34402(16) 0.96277(18) 0.14329(10) 0.0201 Uani 1.0000
C C2 0.28607(16) 1.11710(17) 0.19551(11) 0.0207 Uani 1.0000
C C3 0.34232(16) 1.08204(17) 0.31427(11) 0.0217 Uani 1.0000
C C4 0.45586(16) 0.89539(17) 0.37673(10) 0.0210 Uani 1.0000
C C5 0.51642(16) 0.74038(17) 0.32214(10) 0.0188 Uani 1.0000
C C6 0.45694(16) 0.77380(17) 0.20237(10) 0.0194 Uani 1.0000
C C7 0.51289(19) 0.60873(19) 0.14308(12) 0.0269 Uani 1.0000
N N8 0.63360(16) 0.55949(16) 0.38422(10) 0.0277 Uani 1.0000
Cl Cl9 0.14163(4) 1.34735(4) 0.11329(3) 0.0293 Uani 1.0000
F F10 0.28435(11) 0.99849(12) 0.02806(6) 0.0291 Uani 1.0000
H H31 0.3012 1.1851 0.3475 0.0277 Uiso 1.0000
H H41 0.4953 0.8705 0.4581 0.0257 Uiso 1.0000
H H71 0.6503 0.5518 0.1414 0.0420 Uiso 1.0000
H H72 0.4641 0.5027 0.1863 0.0416 Uiso 1.0000
H H73 0.4639 0.6536 0.0618 0.0429 Uiso 1.0000
H H9 0.6698 0.4664 0.3519 0.0324 Uiso 1.0000
H H11 0.6736 0.5392 0.4585 0.0317 Uiso 1.0000
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.0033 0.0016 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.1484 0.1585 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0171 0.0103 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 'International Tables Vol C 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
_geom_angle_publ_flag
N12 C11 C15 107.80(9) no
N12 C11 O17 124.27(11) no
C15 C11 O17 127.93(11) no
C11 N12 C13 113.60(10) no
C11 N12 H1 125.7 no
C13 N12 H1 120.5 no
N12 C13 C14 108.74(9) no
N12 C13 O16 123.80(11) no
C14 C13 O16 127.46(11) no
C13 C14 C15 104.82(9) no
C13 C14 H141 109.5 no
C15 C14 H141 111.9 no
C13 C14 H142 109.2 no
C15 C14 H142 111.7 no
H141 C14 H142 109.5 no
C14 C15 C11 104.97(9) no
C14 C15 H151 114.0 no
C11 C15 H151 109.0 no
C14 C15 H152 112.8 no
C11 C15 H152 109.9 no
H151 C15 H152 106.2 no
C2 C1 C6 123.78(11) no
C2 C1 F10 118.07(10) no
C6 C1 F10 118.14(10) no
C1 C2 C3 118.84(11) no
C1 C2 Cl9 119.74(9) no
C3 C2 Cl9 121.41(9) no
C2 C3 C4 119.37(11) no
C2 C3 H31 117.6 no
C4 C3 H31 123.1 no
C3 C4 C5 121.32(11) no
C3 C4 H41 119.8 no
C5 C4 H41 118.9 no
C4 C5 C6 119.65(11) no
C4 C5 N8 120.21(11) no
C6 C5 N8 120.13(10) no
C5 C6 C1 117.02(10) no
C5 C6 C7 120.92(11) no
C1 C6 C7 122.05(11) no
C6 C7 H71 111.7 no
C6 C7 H72 111.2 no
H71 C7 H72 106.7 no
C6 C7 H73 111.5 no
H71 C7 H73 108.1 no
H72 C7 H73 107.4 no
C5 N8 H9 120.4 no
C5 N8 H11 120.3 no
H9 N8 H11 119.3 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C11 N12 1.3890(14) no
C11 C15 1.5141(16) no
C11 O17 1.2075(14) no
N12 C13 1.3689(15) no
N12 H1 0.852 no
C13 C14 1.5082(16) no
C13 O16 1.2235(14) no
C14 C15 1.5309(16) no
C14 H141 0.947 no
C14 H142 0.970 no
C15 H151 0.943 no
C15 H152 0.968 no
C1 C2 1.3848(17) no
C1 C6 1.3826(16) no
C1 F10 1.3569(13) no
C2 C3 1.3885(17) no
C2 Cl9 1.7335(12) no
C3 C4 1.3826(16) no
C3 H31 0.913 no
C4 C5 1.4075(16) no
C4 H41 0.952 no
C5 C6 1.4096(16) no
C5 N8 1.3629(14) no
C6 C7 1.5076(16) no
C7 H71 0.968 no
C7 H72 0.963 no
C7 H73 0.955 no
N8 H9 0.842 no
N8 H11 0.882 no
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
N12 H1 O16 2_756 0.85 2.11 2.945(2) 168 yes
N8 H9 O16 2_756 0.84 2.18 2.915(2) 147 yes
N8 H11 O17 . 0.88 2.17 3.030(2) 166 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655532
