#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/04/2210433.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_2210433
loop_
_publ_author_name
'Chen, Ping'
'Zhang, Ling'
'Li, Dan'
_publ_section_title
;
 N-(4-Bromobenzyl)phthalimide
;
_journal_coeditor_code           XU2085
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3691
_journal_page_last               o3692
_journal_paper_doi               10.1107/S1600536806029552
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C15 H10 Br N O2'
_chemical_formula_moiety         'C15 H10 Br N O2'
_chemical_formula_sum            'C15 H10 Br N O2'
_chemical_formula_weight         316.15
_chemical_melting_point          406.9(3)
_chemical_name_systematic
;
N-(4-bromobenzyl)phthaimide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 103.701(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.086(3)
_cell_length_b                   14.174(3)
_cell_length_c                   7.1967(14)
_cell_measurement_reflns_used    1760
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      22.4
_cell_measurement_theta_min      3.2
_cell_volume                     1296.9(5)
_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 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.047
_diffrn_reflns_av_sigmaI/netI    0.056
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            7134
_diffrn_reflns_theta_full        26.4
_diffrn_reflns_theta_max         26.4
_diffrn_reflns_theta_min         1.6
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.165
_exptl_absorpt_correction_T_max  0.666
_exptl_absorpt_correction_T_min  0.517
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.76
_refine_diff_density_min         -0.85
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2637
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.098
_refine_ls_R_factor_gt           0.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0542P)²+1.3278P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.109
_refine_ls_wR_factor_ref         0.138
_reflns_number_gt                1492
_reflns_number_total             2637
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2085.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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:

'_chemical_melting_point' value '406.5-407.2' was changed to
'406.9(3)' - the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '406.5-407.2' was changed to
'406.9(3)' - the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Monoclinic' changed to
'monoclinic' 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_original_cell_volume        1297.0(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2210433
_cod_database_fobs_code          2210433
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_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 0.38537(4) 0.38196(4) 0.08972(8) 0.0824(3) Uani d . 1
O O1 0.8818(3) 0.5306(2) 0.8005(5) 0.0720(9) Uani d . 1
O O2 0.8676(2) 0.2094(2) 0.7668(5) 0.0612(8) Uani d . 1
N N1 0.8511(3) 0.3705(2) 0.7931(5) 0.0469(8) Uani d . 1
C C1 0.9107(3) 0.4509(3) 0.7820(6) 0.0492(10) Uani d . 1
C C2 1.0113(3) 0.4163(3) 0.7446(5) 0.0454(10) Uani d . 1
C C3 1.0978(4) 0.4651(3) 0.7193(6) 0.0595(12) Uani d . 1
H H3 1.0999 0.5307 0.7237 0.071 Uiso calc R 1
C C4 1.1809(4) 0.4138(4) 0.6875(7) 0.0669(13) Uani d . 1
H H4 1.2406 0.4449 0.6706 0.080 Uiso calc R 1
C C5 1.1770(4) 0.3155(4) 0.6801(7) 0.0644(12) Uani d . 1
H H5 1.2343 0.2823 0.6580 0.077 Uiso calc R 1
C C6 1.0898(3) 0.2661(3) 0.7050(6) 0.0517(11) Uani d . 1
H H6 1.0873 0.2005 0.7003 0.062 Uiso calc R 1
C C7 1.0071(3) 0.3185(3) 0.7369(5) 0.0441(9) Uani d . 1
C C8 0.9032(3) 0.2884(3) 0.7658(5) 0.0469(10) Uani d . 1
C C9 0.7449(3) 0.3728(3) 0.8241(6) 0.0549(11) Uani d . 1
H H9A 0.7378 0.4286 0.8980 0.066 Uiso calc R 1
H H9B 0.7353 0.3182 0.8993 0.066 Uiso calc R 1
C C10 0.6587(3) 0.3736(2) 0.6412(6) 0.0452(9) Uani d . 1
C C11 0.6796(3) 0.3773(3) 0.4639(6) 0.0525(10) Uani d . 1
H H11 0.7491 0.3783 0.4537 0.063 Uiso calc R 1
C C12 0.5989(4) 0.3795(3) 0.2983(7) 0.0617(12) Uani d . 1
H H12 0.6142 0.3822 0.1786 0.074 Uiso calc R 1
C C13 0.4967(3) 0.3777(3) 0.3142(7) 0.0554(11) Uani d . 1
C C14 0.4741(3) 0.3732(3) 0.4894(8) 0.0661(13) Uani d . 1
H H14 0.4046 0.3719 0.4993 0.079 Uiso calc R 1
C C15 0.5547(4) 0.3705(3) 0.6514(7) 0.0644(12) Uani d . 1
H H15 0.5388 0.3665 0.7705 0.077 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
Br1 0.0596(4) 0.0858(4) 0.0918(5) 0.0053(3) -0.0021(3) -0.0077(3)
O1 0.093(3) 0.0377(16) 0.089(2) 0.0098(16) 0.0292(19) -0.0017(16)
O2 0.064(2) 0.0399(16) 0.081(2) -0.0040(14) 0.0206(16) 0.0019(15)
N1 0.0480(19) 0.0386(18) 0.055(2) 0.0037(15) 0.0130(16) 0.0002(15)
C1 0.060(3) 0.042(2) 0.045(2) 0.000(2) 0.010(2) -0.0011(18)
C2 0.055(3) 0.040(2) 0.037(2) -0.0019(19) 0.0020(19) 0.0007(16)
C3 0.060(3) 0.055(3) 0.059(3) -0.012(2) 0.006(2) 0.002(2)
C4 0.049(3) 0.081(3) 0.068(3) -0.013(3) 0.007(2) 0.007(3)
C5 0.052(3) 0.079(3) 0.063(3) 0.008(2) 0.014(2) 0.004(3)
C6 0.053(3) 0.048(2) 0.050(3) 0.006(2) 0.004(2) -0.0003(19)
C7 0.049(2) 0.043(2) 0.037(2) 0.0003(18) 0.0029(18) -0.0008(17)
C8 0.058(3) 0.040(2) 0.040(2) 0.0028(19) 0.0051(19) 0.0012(18)
C9 0.062(3) 0.053(3) 0.053(3) 0.007(2) 0.020(2) 0.005(2)
C10 0.048(2) 0.034(2) 0.058(3) 0.0040(17) 0.0217(19) 0.0031(19)
C11 0.043(2) 0.060(3) 0.059(3) 0.001(2) 0.022(2) -0.002(2)
C12 0.060(3) 0.074(3) 0.054(3) 0.004(2) 0.021(2) 0.006(2)
C13 0.047(2) 0.050(2) 0.069(3) 0.001(2) 0.014(2) -0.003(2)
C14 0.040(2) 0.068(3) 0.095(4) 0.000(2) 0.027(3) 0.001(3)
C15 0.059(3) 0.076(3) 0.067(3) 0.003(2) 0.032(2) 0.008(3)
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
C8 N1 C1 112.2(3)
C8 N1 C9 124.0(3)
C1 N1 C9 123.7(3)
O1 C1 N1 124.4(4)
O1 C1 C2 129.8(4)
N1 C1 C2 105.7(3)
C3 C2 C7 121.6(4)
C3 C2 C1 130.5(4)
C7 C2 C1 107.9(4)
C4 C3 C2 117.7(4)
C4 C3 H3 121.1
C2 C3 H3 121.1
C3 C4 C5 120.8(4)
C3 C4 H4 119.6
C5 C4 H4 119.6
C6 C5 C4 121.6(4)
C6 C5 H5 119.2
C4 C5 H5 119.2
C7 C6 C5 116.9(4)
C7 C6 H6 121.5
C5 C6 H6 121.5
C6 C7 C2 121.3(4)
C6 C7 C8 130.6(4)
C2 C7 C8 108.1(4)
O2 C8 N1 124.8(4)
O2 C8 C7 129.1(4)
N1 C8 C7 106.1(3)
N1 C9 C10 114.0(3)
N1 C9 H9A 108.8
C10 C9 H9A 108.8
N1 C9 H9B 108.8
C10 C9 H9B 108.8
H9A C9 H9B 107.6
C11 C10 C15 117.9(4)
C11 C10 C9 122.5(4)
C15 C10 C9 119.5(4)
C10 C11 C12 121.4(4)
C10 C11 H11 119.3
C12 C11 H11 119.3
C13 C12 C11 119.0(4)
C13 C12 H12 120.5
C11 C12 H12 120.5
C14 C13 C12 120.6(4)
C14 C13 Br1 119.7(3)
C12 C13 Br1 119.7(4)
C13 C14 C15 119.7(4)
C13 C14 H14 120.2
C15 C14 H14 120.2
C14 C15 C10 121.4(4)
C14 C15 H15 119.3
C10 C15 H15 119.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C13 1.903(5)
O1 C1 1.208(5)
O2 C8 1.213(5)
N1 C8 1.385(5)
N1 C1 1.394(5)
N1 C9 1.459(5)
C1 C2 1.488(6)
C2 C3 1.375(6)
C2 C7 1.389(6)
C3 C4 1.372(6)
C3 H3 0.9300
C4 C5 1.394(7)
C4 H4 0.9300
C5 C6 1.386(6)
C5 H5 0.9300
C6 C7 1.376(6)
C6 H6 0.9300
C7 C8 1.485(6)
C9 C10 1.517(6)
C9 H9A 0.9700
C9 H9B 0.9700
C10 C11 1.368(6)
C10 C15 1.381(6)
C11 C12 1.393(6)
C11 H11 0.9300
C12 C13 1.368(6)
C12 H12 0.9300
C13 C14 1.364(7)
C14 C15 1.375(7)
C14 H14 0.9300
C15 H15 0.9300
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
C3 H3 O2 2_756 0.93 2.570 3.491(5) 172 yes
C6 H6 O1 2_746 0.93 2.440 3.360(5) 169 yes
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 179.8(4)
C9 N1 C1 O1 1.5(6)
C8 N1 C1 C2 -0.3(4)
C9 N1 C1 C2 -178.5(3)
O1 C1 C2 C3 -0.7(7)
N1 C1 C2 C3 179.4(4)
O1 C1 C2 C7 179.5(4)
N1 C1 C2 C7 -0.5(4)
C7 C2 C3 C4 -0.5(6)
C1 C2 C3 C4 179.7(4)
C2 C3 C4 C5 0.4(7)
C3 C4 C5 C6 -0.2(7)
C4 C5 C6 C7 0.1(6)
C5 C6 C7 C2 -0.3(6)
C5 C6 C7 C8 179.0(4)
C3 C2 C7 C6 0.5(6)
C1 C2 C7 C6 -179.7(3)
C3 C2 C7 C8 -178.9(4)
C1 C2 C7 C8 0.9(4)
C1 N1 C8 O2 -179.2(4)
C9 N1 C8 O2 -0.9(6)
C1 N1 C8 C7 0.8(4)
C9 N1 C8 C7 179.1(3)
C6 C7 C8 O2 -0.4(7)
C2 C7 C8 O2 178.9(4)
C6 C7 C8 N1 179.6(4)
C2 C7 C8 N1 -1.1(4)
C8 N1 C9 C10 -85.9(4)
C1 N1 C9 C10 92.2(4)
N1 C9 C10 C11 -3.6(5)
N1 C9 C10 C15 176.4(3)
C15 C10 C11 C12 1.1(6)
C9 C10 C11 C12 -178.9(4)
C10 C11 C12 C13 -0.2(6)
C11 C12 C13 C14 -0.4(6)
C11 C12 C13 Br1 179.3(3)
C12 C13 C14 C15 0.0(7)
Br1 C13 C14 C15 -179.7(3)
C13 C14 C15 C10 0.9(7)
C11 C10 C15 C14 -1.5(6)
C9 C10 C15 C14 178.5(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 781410
