#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/42/2214215.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_2214215
loop_
_publ_author_name
'Liang, Zu-Pei'
'Li, Jian'
'Yang Hua'
'Wang, Hong-Liang'
_publ_section_title
;
 4-(5-Bromo-1,3-dioxoisoindolin-2-yl)benzoic acid
 N,N-dimethylformamide solvate
;
_journal_coeditor_code           HB2427
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3065
_journal_page_last               o3065
_journal_paper_doi               10.1107/S1600536807025913
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C15 H8 Br N O4, C3 H7 N O'
_chemical_formula_moiety         'C15 H8 Br N O4, C3 H7 N O'
_chemical_formula_sum            'C18 H15 Br N2 O5'
_chemical_formula_weight         419.23
_chemical_name_systematic
;4-(5-Bromo-1,3-dioxoisoindolin-2-yl)benzoic acid N,N-dimethylformamide
 solvate
;
_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
_cell_angle_alpha                101.231(2)
_cell_angle_beta                 93.417(3)
_cell_angle_gamma                107.273(2)
_cell_formula_units_Z            2
_cell_length_a                   5.9686(9)
_cell_length_b                   8.3214(12)
_cell_length_c                   19.058(3)
_cell_measurement_reflns_used    2063
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.06
_cell_measurement_theta_min      2.63
_cell_volume                     879.6(2)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       ω
_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  0.0218
_diffrn_reflns_av_sigmaI/netI    0.0438
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5114
_diffrn_reflns_theta_full        26.40
_diffrn_reflns_theta_max         26.40
_diffrn_reflns_theta_min         1.10
_exptl_absorpt_coefficient_mu    2.369
_exptl_absorpt_correction_T_max  0.764
_exptl_absorpt_correction_T_min  0.578
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.417
_refine_ls_extinction_coef       0.062(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3561
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0396
_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)+(0.061P)²+0.029P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.1179
_reflns_number_gt                2643
_reflns_number_total             3561
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2427.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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               2214215
_cod_database_fobs_code          2214215
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
Br Br1 -0.43214(7) 0.20856(4) 0.48540(2) 0.0632(2) Uani d . 1
O O1 -0.1509(4) 0.8323(3) 0.37081(13) 0.0516(6) Uani d . 1
O O2 0.3821(4) 0.5901(3) 0.26776(14) 0.0597(6) Uani d . 1
O O3 0.7047(4) 1.3643(3) 0.17597(14) 0.0619(7) Uani d . 1
H H3 0.7489 1.4260 0.1475 0.093 Uiso calc R 1
O O4 0.3495(4) 1.3123(3) 0.11588(13) 0.0604(6) Uani d . 1
N N1 0.1307(4) 0.7455(3) 0.30854(14) 0.0405(6) Uani d . 1
C C1 -0.0493(5) 0.7278(4) 0.35266(16) 0.0390(7) Uani d . 1
C C2 -0.0781(5) 0.5619(4) 0.37446(16) 0.0369(6) Uani d . 1
C C3 -0.2363(5) 0.4823(4) 0.41681(17) 0.0415(7) Uani d . 1
H H3A -0.3506 0.5283 0.4351 0.050 Uiso calc R 1
C C4 -0.2140(6) 0.3285(4) 0.43040(17) 0.0442(7) Uani d . 1
C C5 -0.0431(6) 0.2596(4) 0.40437(17) 0.0469(8) Uani d . 1
H H5 -0.0324 0.1581 0.4156 0.056 Uiso calc R 1
C C6 0.1121(6) 0.3415(4) 0.36169(17) 0.0443(7) Uani d . 1
H H6 0.2279 0.2968 0.3438 0.053 Uiso calc R 1
C C7 0.0890(5) 0.4929(4) 0.34652(16) 0.0399(7) Uani d . 1
C C8 0.2262(6) 0.6062(4) 0.30239(18) 0.0429(7) Uani d . 1
C C9 0.2166(5) 0.8872(4) 0.27445(16) 0.0374(7) Uani d . 1
C C10 0.0590(5) 0.9331(4) 0.23213(16) 0.0398(7) Uani d . 1
H H10 -0.1025 0.8760 0.2275 0.048 Uiso calc R 1
C C11 0.1456(5) 1.0653(4) 0.19680(16) 0.0406(7) Uani d . 1
H H11 0.0410 1.0969 0.1684 0.049 Uiso calc R 1
C C12 0.3859(5) 1.1507(4) 0.20329(15) 0.0359(6) Uani d . 1
C C13 0.5403(5) 1.1039(4) 0.24672(17) 0.0426(7) Uani d . 1
H H13 0.7019 1.1609 0.2517 0.051 Uiso calc R 1
C C14 0.4556(5) 0.9732(4) 0.28260(17) 0.0425(7) Uani d . 1
H H14 0.5595 0.9436 0.3121 0.051 Uiso calc R 1
C C15 0.4749(5) 1.2844(4) 0.16040(17) 0.0430(7) Uani d . 1
O O5 -0.1165(4) 0.5819(3) 0.09856(14) 0.0597(6) Uani d . 1
N N2 0.2246(4) 0.7231(4) 0.06190(15) 0.0479(7) Uani d . 1
C C16 0.0984(6) 0.6147(4) 0.09704(18) 0.0497(8) Uani d . 1
H H16 0.1766 0.5586 0.1226 0.060 Uiso calc R 1
C C17 0.1156(6) 0.8105(5) 0.0182(2) 0.0603(9) Uani d . 1
H H17A -0.0530 0.7689 0.0173 0.090 Uiso calc R 1
H H17B 0.1554 0.7881 -0.0300 0.090 Uiso calc R 1
H H17C 0.1721 0.9325 0.0384 0.090 Uiso calc R 1
C C18 0.4768(7) 0.7532(7) 0.0622(3) 0.0818(13) Uani d . 1
H H18A 0.5272 0.6866 0.0920 0.123 Uiso calc R 1
H H18B 0.5599 0.8736 0.0808 0.123 Uiso calc R 1
H H18C 0.5102 0.7193 0.0138 0.123 Uiso calc R 1
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'
Br Br -0.2901 2.4595 '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
C15 O3 H3 109.5
C1 N1 C8 111.7(2)
C1 N1 C9 125.2(2)
C8 N1 C9 123.1(2)
O1 C1 N1 125.7(3)
O1 C1 C2 128.4(3)
N1 C1 C2 105.8(2)
C7 C2 C3 122.2(3)
C7 C2 C1 108.7(3)
C3 C2 C1 129.1(3)
C2 C3 C4 115.9(3)
C2 C3 H3A 122.1
C4 C3 H3A 122.1
C5 C4 C3 122.8(3)
C5 C4 Br1 119.2(2)
C3 C4 Br1 118.1(3)
C4 C5 C6 120.1(3)
C4 C5 H5 119.9
C6 C5 H5 119.9
C5 C6 C7 117.7(3)
C5 C6 H6 121.1
C7 C6 H6 121.1
C2 C7 C6 121.3(3)
C2 C7 C8 109.0(2)
C6 C7 C8 129.7(3)
O2 C8 N1 125.2(3)
O2 C8 C7 130.0(3)
N1 C8 C7 104.8(3)
C14 C9 C10 120.8(3)
C14 C9 N1 119.5(2)
C10 C9 N1 119.7(3)
C11 C10 C9 119.1(3)
C11 C10 H10 120.4
C9 C10 H10 120.4
C12 C11 C10 120.8(3)
C12 C11 H11 119.6
C10 C11 H11 119.6
C11 C12 C13 119.0(3)
C11 C12 C15 119.4(3)
C13 C12 C15 121.5(3)
C14 C13 C12 120.6(3)
C14 C13 H13 119.7
C12 C13 H13 119.7
C9 C14 C13 119.6(3)
C9 C14 H14 120.2
C13 C14 H14 120.2
O4 C15 O3 124.2(3)
O4 C15 C12 122.9(3)
O3 C15 C12 112.8(3)
C16 N2 C17 121.3(3)
C16 N2 C18 121.3(3)
C17 N2 C18 117.3(3)
O5 C16 N2 124.7(3)
O5 C16 H16 117.6
N2 C16 H16 117.6
N2 C17 H17A 109.5
N2 C17 H17B 109.5
H17A C17 H17B 109.5
N2 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
N2 C18 H18A 109.5
N2 C18 H18B 109.5
H18A C18 H18B 109.5
N2 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C4 1.895(3)
O1 C1 1.210(3)
O2 C8 1.197(4)
O3 C15 1.321(4)
O3 H3 0.8200
O4 C15 1.199(4)
N1 C1 1.395(4)
N1 C8 1.425(4)
N1 C9 1.433(3)
C1 C2 1.484(4)
C2 C7 1.375(4)
C2 C3 1.382(4)
C3 C4 1.396(4)
C3 H3A 0.9300
C4 C5 1.383(5)
C5 C6 1.384(4)
C5 H5 0.9300
C6 C7 1.389(4)
C6 H6 0.9300
C7 C8 1.483(4)
C9 C14 1.377(4)
C9 C10 1.387(4)
C10 C11 1.387(4)
C10 H10 0.9300
C11 C12 1.385(4)
C11 H11 0.9300
C12 C13 1.391(4)
C12 C15 1.497(4)
C13 C14 1.382(4)
C13 H13 0.9300
C14 H14 0.9300
O5 C16 1.233(4)
N2 C16 1.312(4)
N2 C17 1.448(4)
N2 C18 1.450(4)
C16 H16 0.9300
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 0.9600
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
O3 H3 O5 1_665 0.82 1.77 2.583(3) 170
C5 H5 O1 1_545 0.93 2.54 3.343(4) 144
C14 H14 O1 1_655 0.93 2.49 3.413(4) 170
C16 H16 O4 1_545 0.93 2.54 3.352(4) 146
C18 H18A O5 1_655 0.96 2.53 3.262(5) 133
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
C8 N1 C1 O1 175.1(3)
C9 N1 C1 O1 -3.3(5)
C8 N1 C1 C2 -2.1(3)
C9 N1 C1 C2 179.4(2)
O1 C1 C2 C7 -174.2(3)
N1 C1 C2 C7 3.0(3)
O1 C1 C2 C3 4.4(5)
N1 C1 C2 C3 -178.5(3)
C7 C2 C3 C4 0.9(4)
C1 C2 C3 C4 -177.4(3)
C2 C3 C4 C5 0.9(4)
C2 C3 C4 Br1 -177.9(2)
C3 C4 C5 C6 -1.3(5)
Br1 C4 C5 C6 177.4(2)
C4 C5 C6 C7 0.0(5)
C3 C2 C7 C6 -2.2(5)
C1 C2 C7 C6 176.4(3)
C3 C2 C7 C8 178.6(3)
C1 C2 C7 C8 -2.7(3)
C5 C6 C7 C2 1.7(4)
C5 C6 C7 C8 -179.3(3)
C1 N1 C8 O2 180.0(3)
C9 N1 C8 O2 -1.5(5)
C1 N1 C8 C7 0.5(3)
C9 N1 C8 C7 179.1(2)
C2 C7 C8 O2 -177.9(3)
C6 C7 C8 O2 3.0(6)
C2 C7 C8 N1 1.4(3)
C6 C7 C8 N1 -177.6(3)
C1 N1 C9 C14 128.3(3)
C8 N1 C9 C14 -50.0(4)
C1 N1 C9 C10 -53.4(4)
C8 N1 C9 C10 128.3(3)
C14 C9 C10 C11 1.2(4)
N1 C9 C10 C11 -177.1(3)
C9 C10 C11 C12 0.1(4)
C10 C11 C12 C13 -0.9(4)
C10 C11 C12 C15 175.8(3)
C11 C12 C13 C14 0.4(5)
C15 C12 C13 C14 -176.2(3)
C10 C9 C14 C13 -1.7(5)
N1 C9 C14 C13 176.6(3)
C12 C13 C14 C9 0.9(5)
C11 C12 C15 O4 -6.1(5)
C13 C12 C15 O4 170.5(3)
C11 C12 C15 O3 175.2(3)
C13 C12 C15 O3 -8.2(4)
C17 N2 C16 O5 -2.6(5)
C18 N2 C16 O5 -179.3(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21124193
