#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/32/2223225.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_2223225
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Goh, Jia Hao'
'Chandrakantha, B.'
'Isloor, Arun M.'
_publ_section_title
;
 1-Dibromomethyl-4-methoxy-2-nitrobenzene
;
_journal_coeditor_code           WN2343
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2193
_journal_page_last               o2194
_journal_paper_doi               10.1107/S1600536809031833
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C8 H7 Br2 N O3'
_chemical_formula_moiety         'C8 H7 Br2 N O3'
_chemical_formula_sum            'C8 H7 Br2 N O3'
_chemical_formula_weight         324.97
_chemical_name_systematic
;
1-Dibromomethyl-4-methoxy-2-nitrobenzene
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                106.2850(10)
_cell_angle_beta                 99.6910(10)
_cell_angle_gamma                102.4010(10)
_cell_formula_units_Z            4
_cell_length_a                   7.95910(10)
_cell_length_b                   11.1949(2)
_cell_length_c                   12.2509(2)
_cell_measurement_reflns_used    9885
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      35.08
_cell_measurement_theta_min      2.18
_cell_volume                     992.45(3)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker SMART APEXII 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  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            32659
_diffrn_reflns_theta_full        35.26
_diffrn_reflns_theta_max         35.26
_diffrn_reflns_theta_min         1.97
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    8.147
_exptl_absorpt_correction_T_max  0.3111
_exptl_absorpt_correction_T_min  0.2096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.175
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.279
_exptl_crystal_size_mid          0.248
_exptl_crystal_size_min          0.187
_refine_diff_density_max         0.781
_refine_diff_density_min         -0.472
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         8800
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0261
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0361P)²+0.2346P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0631
_refine_ls_wR_factor_ref         0.0663
_reflns_number_gt                7332
_reflns_number_total             8800
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn2343.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               2223225
_cod_database_fobs_code          2223225
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1A 0.79537(2) 1.230776(16) 0.197580(14) 0.02458(4) Uani d . 1 . .
Br Br2A 0.90786(2) 1.101536(16) 0.387687(13) 0.02180(4) Uani d . 1 . .
O O1A 0.76010(16) 0.62902(12) -0.10724(10) 0.0229(2) Uani d . 1 . .
O O2A 0.30267(16) 0.76549(13) 0.10327(11) 0.0265(2) Uani d . 1 . .
O O3A 0.37293(16) 0.96938(13) 0.11963(11) 0.0257(2) Uani d . 1 . .
N N1A 0.40781(17) 0.86506(14) 0.10586(11) 0.0208(2) Uani d . 1 . .
C C1A 0.8937(2) 0.94163(16) 0.11837(13) 0.0209(3) Uani d . 1 . .
H H1AA 0.9990 1.0061 0.1578 0.025 Uiso calc R 1 . .
C C2A 0.8985(2) 0.83283(16) 0.03310(13) 0.0216(3) Uani d . 1 . .
H H2AA 1.0052 0.8260 0.0142 0.026 Uiso calc R 1 . .
C C3A 0.7427(2) 0.73241(15) -0.02523(13) 0.0195(3) Uani d . 1 . .
C C4A 0.58321(19) 0.74374(15) 0.00283(13) 0.0188(2) Uani d . 1 . .
H H4AA 0.4792 0.6770 -0.0335 0.023 Uiso calc R 1 . .
C C5A 0.58299(19) 0.85699(15) 0.08631(13) 0.0185(2) Uani d . 1 . .
C C6A 0.73536(19) 0.95856(15) 0.14790(13) 0.0184(2) Uani d . 1 . .
C C7A 0.7370(2) 1.07568(15) 0.24351(13) 0.0196(3) Uani d . 1 . .
C C8A 0.6054(2) 0.52136(17) -0.16335(15) 0.0256(3) Uani d . 1 . .
H H8AA 0.6344 0.4546 -0.2193 0.038 Uiso calc R 1 . .
H H8AB 0.5141 0.5491 -0.2029 0.038 Uiso calc R 1 . .
H H8AC 0.5640 0.4883 -0.1055 0.038 Uiso calc R 1 . .
Br Br1B -0.20637(2) 0.726206(17) 0.325018(14) 0.02462(4) Uani d . 1 . .
Br Br2B -0.10244(2) 0.523519(16) 0.125556(13) 0.02342(4) Uani d . 1 . .
O O1B 0.50849(16) 0.63292(12) 0.60857(11) 0.0243(2) Uani d . 1 . .
O O2B 0.49443(16) 0.92884(12) 0.36858(11) 0.0252(2) Uani d . 1 . .
O O3B 0.22098(17) 0.93622(12) 0.34859(12) 0.0261(2) Uani d . 1 . .
N N1B 0.33898(17) 0.88484(13) 0.36914(11) 0.0197(2) Uani d . 1 . .
C C1B 0.1045(2) 0.56681(15) 0.38962(13) 0.0206(3) Uani d . 1 . .
H H1BA -0.0019 0.5017 0.3575 0.025 Uiso calc R 1 . .
C C2B 0.2309(2) 0.55536(16) 0.47501(14) 0.0215(3) Uani d . 1 . .
H H2BA 0.2081 0.4840 0.5005 0.026 Uiso calc R 1 . .
C C3B 0.3935(2) 0.65079(16) 0.52360(13) 0.0200(3) Uani d . 1 . .
C C4B 0.4281(2) 0.75603(15) 0.48395(13) 0.0199(3) Uani d . 1 . .
H H4BA 0.5370 0.8186 0.5131 0.024 Uiso calc R 1 . .
C C5B 0.29538(19) 0.76575(15) 0.39929(13) 0.0180(2) Uani d . 1 . .
C C6B 0.13101(19) 0.67357(15) 0.34948(13) 0.0185(2) Uani d . 1 . .
C C7B -0.0114(2) 0.68337(16) 0.25833(13) 0.0203(3) Uani d . 1 . .
C C8B 0.6731(2) 0.73163(19) 0.66117(16) 0.0289(3) Uani d . 1 . .
H H8BA 0.7436 0.7088 0.7196 0.043 Uiso calc R 1 . .
H H8BB 0.6504 0.8126 0.6971 0.043 Uiso calc R 1 . .
H H8BC 0.7359 0.7397 0.6021 0.043 Uiso calc R 1 . .
H H7A 0.627(3) 1.0704(19) 0.2645(17) 0.013(4) Uiso d . 1 . .
H H7B 0.022(3) 0.747(2) 0.226(2) 0.028(6) Uiso d . 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3A O1A C8A . . 117.29(13) ?
O3A N1A O2A . . 123.97(14) ?
O3A N1A C5A . . 118.23(13) ?
O2A N1A C5A . . 117.75(14) ?
C2A C1A C6A . . 122.27(14) ?
C2A C1A H1AA . . 118.9 ?
C6A C1A H1AA . . 118.9 ?
C1A C2A C3A . . 120.06(14) ?
C1A C2A H2AA . . 120.0 ?
C3A C2A H2AA . . 120.0 ?
O1A C3A C4A . . 124.35(14) ?
O1A C3A C2A . . 115.97(13) ?
C4A C3A C2A . . 119.68(14) ?
C5A C4A C3A . . 118.44(14) ?
C5A C4A H4AA . . 120.8 ?
C3A C4A H4AA . . 120.8 ?
C4A C5A C6A . . 123.78(14) ?
C4A C5A N1A . . 115.23(13) ?
C6A C5A N1A . . 120.98(14) ?
C5A C6A C1A . . 115.70(14) ?
C5A C6A C7A . . 123.71(13) ?
C1A C6A C7A . . 120.52(13) ?
C6A C7A Br2A . . 111.59(11) ?
C6A C7A Br1A . . 110.77(10) ?
Br2A C7A Br1A . . 108.66(7) ?
C6A C7A H7A . . 113.2(12) ?
Br2A C7A H7A . . 104.8(12) ?
Br1A C7A H7A . . 107.5(12) ?
O1A C8A H8AA . . 109.5 ?
O1A C8A H8AB . . 109.5 ?
H8AA C8A H8AB . . 109.5 ?
O1A C8A H8AC . . 109.5 ?
H8AA C8A H8AC . . 109.5 ?
H8AB C8A H8AC . . 109.5 ?
C3B O1B C8B . . 116.75(13) ?
O3B N1B O2B . . 123.87(14) ?
O3B N1B C5B . . 118.83(12) ?
O2B N1B C5B . . 117.28(13) ?
C2B C1B C6B . . 122.16(14) ?
C2B C1B H1BA . . 118.9 ?
C6B C1B H1BA . . 118.9 ?
C1B C2B C3B . . 120.25(14) ?
C1B C2B H2BA . . 119.9 ?
C3B C2B H2BA . . 119.9 ?
O1B C3B C4B . . 124.10(14) ?
O1B C3B C2B . . 116.25(14) ?
C4B C3B C2B . . 119.65(14) ?
C3B C4B C5B . . 118.43(14) ?
C3B C4B H4BA . . 120.8 ?
C5B C4B H4BA . . 120.8 ?
C4B C5B C6B . . 123.70(14) ?
C4B C5B N1B . . 114.52(13) ?
C6B C5B N1B . . 121.73(13) ?
C5B C6B C1B . . 115.76(14) ?
C5B C6B C7B . . 123.88(14) ?
C1B C6B C7B . . 120.36(13) ?
C6B C7B Br2B . . 111.47(11) ?
C6B C7B Br1B . . 110.83(10) ?
Br2B C7B Br1B . . 109.65(7) ?
C6B C7B H7B . . 115.7(15) ?
Br2B C7B H7B . . 105.1(15) ?
Br1B C7B H7B . . 103.7(15) ?
O1B C8B H8BA . . 109.5 ?
O1B C8B H8BB . . 109.5 ?
H8BA C8B H8BB . . 109.5 ?
O1B C8B H8BC . . 109.5 ?
H8BA C8B H8BC . . 109.5 ?
H8BB C8B H8BC . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1A C7A . 1.9587(15) ?
Br2A C7A . 1.9462(15) ?
O1A C3A . 1.3535(19) ?
O1A C8A . 1.433(2) ?
O2A N1A . 1.2306(18) ?
O3A N1A . 1.2305(19) ?
N1A C5A . 1.4710(19) ?
C1A C2A . 1.377(2) ?
C1A C6A . 1.405(2) ?
C1A H1AA . 0.9300 ?
C2A C3A . 1.402(2) ?
C2A H2AA . 0.9300 ?
C3A C4A . 1.392(2) ?
C4A C5A . 1.388(2) ?
C4A H4AA . 0.9300 ?
C5A C6A . 1.397(2) ?
C6A C7A . 1.489(2) ?
C7A H7A . 0.948(19) ?
C8A H8AA . 0.9600 ?
C8A H8AB . 0.9600 ?
C8A H8AC . 0.9600 ?
Br1B C7B . 1.9576(16) ?
Br2B C7B . 1.9460(16) ?
O1B C3B . 1.3547(19) ?
O1B C8B . 1.431(2) ?
O2B N1B . 1.2314(17) ?
O3B N1B . 1.2288(18) ?
N1B C5B . 1.4680(19) ?
C1B C2B . 1.378(2) ?
C1B C6B . 1.404(2) ?
C1B H1BA . 0.9300 ?
C2B C3B . 1.401(2) ?
C2B H2BA . 0.9300 ?
C3B C4B . 1.388(2) ?
C4B C5B . 1.395(2) ?
C4B H4BA . 0.9300 ?
C5B C6B . 1.395(2) ?
C6B C7B . 1.497(2) ?
C7B H7B . 0.92(2) ?
C8B H8BA . 0.9600 ?
C8B H8BB . 0.9600 ?
C8B H8BC . 0.9600 ?
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Br1A Br2B 3.5915(3) . 1_665 yes
Br2A Br1B 3.6279(2) . 2_676 yes
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
C7A H7A O2B . 0.95(2) 2.47(2) 3.134(2) 126.8(17) yes
C8B H8BA O1A 1_556 0.9600 2.5200 3.370(2) 148.00 yes
C8A H8AA Cg2 2_665 0.9600 2.9500 3.839(2) 155.00 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6A C1A C2A C3A . . . . -1.9(2) ?
C8A O1A C3A C4A . . . . -3.9(2) ?
C8A O1A C3A C2A . . . . 176.29(14) ?
C1A C2A C3A O1A . . . . -179.68(14) ?
C1A C2A C3A C4A . . . . 0.5(2) ?
O1A C3A C4A C5A . . . . -178.01(14) ?
C2A C3A C4A C5A . . . . 1.8(2) ?
C3A C4A C5A C6A . . . . -2.9(2) ?
C3A C4A C5A N1A . . . . 176.35(13) ?
O3A N1A C5A C4A . . . . -139.68(14) ?
O2A N1A C5A C4A . . . . 37.79(19) ?
O3A N1A C5A C6A . . . . 39.6(2) ?
O2A N1A C5A C6A . . . . -142.94(15) ?
C4A C5A C6A C1A . . . . 1.6(2) ?
N1A C5A C6A C1A . . . . -177.63(13) ?
C4A C5A C6A C7A . . . . -175.35(14) ?
N1A C5A C6A C7A . . . . 5.5(2) ?
C2A C1A C6A C5A . . . . 0.9(2) ?
C2A C1A C6A C7A . . . . 177.90(14) ?
C5A C6A C7A Br2A . . . . 124.47(14) ?
C1A C6A C7A Br2A . . . . -52.30(17) ?
C5A C6A C7A Br1A . . . . -114.33(14) ?
C1A C6A C7A Br1A . . . . 68.89(16) ?
C6B C1B C2B C3B . . . . -1.1(2) ?
C8B O1B C3B C4B . . . . 1.5(2) ?
C8B O1B C3B C2B . . . . -178.30(15) ?
C1B C2B C3B O1B . . . . 178.77(15) ?
C1B C2B C3B C4B . . . . -1.1(2) ?
O1B C3B C4B C5B . . . . -177.36(15) ?
C2B C3B C4B C5B . . . . 2.4(2) ?
C3B C4B C5B C6B . . . . -1.9(2) ?
C3B C4B C5B N1B . . . . 175.71(14) ?
O3B N1B C5B C4B . . . . -142.98(15) ?
O2B N1B C5B C4B . . . . 35.46(19) ?
O3B N1B C5B C6B . . . . 34.7(2) ?
O2B N1B C5B C6B . . . . -146.90(14) ?
C4B C5B C6B C1B . . . . -0.1(2) ?
N1B C5B C6B C1B . . . . -177.56(14) ?
C4B C5B C6B C7B . . . . -179.76(15) ?
N1B C5B C6B C7B . . . . 2.8(2) ?
C2B C1B C6B C5B . . . . 1.6(2) ?
C2B C1B C6B C7B . . . . -178.73(15) ?
C5B C6B C7B Br2B . . . . 130.42(13) ?
C1B C6B C7B Br2B . . . . -49.18(17) ?
C5B C6B C7B Br1B . . . . -107.15(14) ?
C1B C6B C7B Br1B . . . . 73.24(17) ?
