#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/65/2216534.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_2216534
loop_
_publ_author_name
'Liang-zhong Xu'
'Wen-Zhao Bi'
'Kai Zhou'
_publ_section_title
;
 (E)-Ethyl 2-[2-(bromomethyl)phenyl]-2-(methoxyimino)acetate
;
_journal_coeditor_code           HG2343
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4686
_journal_page_last               o4686
_journal_paper_doi               10.1107/S1600536807055869
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C12 H14 Br N O3'
_chemical_formula_moiety         'C12 H14 Br N O3'
_chemical_formula_sum            'C12 H14 Br N O3'
_chemical_formula_weight         300.15
_chemical_name_systematic
;
(E)-Ethyl 2-[2-(bromomethyl)phenyl]-2-(methoxyimino)acetate
;
_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                78.982(5)
_cell_angle_beta                 85.344(5)
_cell_angle_gamma                86.869(6)
_cell_formula_units_Z            2
_cell_length_a                   7.773(2)
_cell_length_b                   8.443(2)
_cell_length_c                   10.472(3)
_cell_measurement_reflns_used    757
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      20.45
_cell_measurement_theta_min      2.63
_cell_volume                     671.8(3)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL(Sheldrick, 2001)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0775
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3405
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.99
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.056
_exptl_absorpt_correction_T_max  0.6093
_exptl_absorpt_correction_T_min  0.5275
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.319
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2324
_refine_ls_number_restraints     102
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.1452
_refine_ls_R_factor_gt           0.0607
_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)+(0.0900P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1413
_refine_ls_wR_factor_ref         0.1886
_reflns_number_gt                1097
_reflns_number_total             2324
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2343.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               2216534
_cod_database_fobs_code          2216534
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 Br1 0.2222(5) 0.9312(3) 0.5699(3) 0.1277(12) Uani d PDU 0.80 A 1
Br Br1' 0.2145(16) 0.9244(16) 0.5155(13) 0.127(5) Uani d PDU 0.20 A 2
O O1 0.6797(4) 0.5967(5) 0.7615(4) 0.0626(12) Uani d . 1 . .
N N1 0.5775(6) 0.6726(7) 0.8473(5) 0.0570(13) Uani d . 1 . .
C C1 0.3974(7) 0.7607(7) 0.5621(6) 0.0660(18) Uani d D 1 . .
H H1A 0.4331 0.7571 0.4717 0.079 Uiso calc R 1 A 1
H H1B 0.4977 0.7828 0.6043 0.079 Uiso calc R 1 A 1
C C2 0.3315(6) 0.6064(7) 0.6261(5) 0.0448(14) Uani d . 1 A .
C C3 0.2597(7) 0.5061(8) 0.5532(6) 0.0583(16) Uani d . 1 . .
H H3 0.2522 0.5401 0.4639 0.070 Uiso calc R 1 A .
C C4 0.2012(8) 0.3596(8) 0.6131(8) 0.0663(18) Uani d . 1 A .
H H4 0.1535 0.2953 0.5633 0.080 Uiso calc R 1 . .
C C5 0.2102(8) 0.3038(8) 0.7431(8) 0.0686(18) Uani d . 1 . .
H H5 0.1709 0.2025 0.7816 0.082 Uiso calc R 1 A .
C C6 0.2796(8) 0.4016(8) 0.8176(6) 0.0631(17) Uani d . 1 A .
H H6 0.2849 0.3660 0.9070 0.076 Uiso calc R 1 . .
C C7 0.3404(6) 0.5502(7) 0.7600(6) 0.0458(14) Uani d . 1 . .
C C8 0.4170(7) 0.6517(7) 0.8421(5) 0.0516(15) Uani d . 1 A .
C C9 0.8561(7) 0.6317(10) 0.7687(7) 0.087(2) Uani d . 1 . .
H H9A 0.8699 0.7460 0.7439 0.130 Uiso calc R 1 . .
H H9B 0.9284 0.5769 0.7107 0.130 Uiso calc R 1 . .
H H9C 0.8885 0.5956 0.8564 0.130 Uiso calc R 1 . .
C C10 0.2964(9) 0.7311(11) 0.9314(7) 0.080(2) Uani d . 1 . .
O O2 0.1487(10) 0.6847(11) 0.9616(8) 0.074(2) Uani d PU 0.70 A 1
O O3 0.3666(9) 0.8488(10) 0.9785(8) 0.068(2) Uani d PDU 0.70 A 1
C C11 0.2622(13) 0.9412(14) 1.0607(9) 0.074(3) Uani d PDU 0.70 A 1
H H11A 0.1412 0.9382 1.0451 0.089 Uiso calc PR 0.70 A 1
H H11B 0.2951 1.0529 1.0414 0.089 Uiso calc PR 0.70 A 1
C C12 0.2900(18) 0.8691(17) 1.2004(10) 0.113(4) Uani d PDU 0.70 A 1
H H12A 0.2222 0.9298 1.2565 0.170 Uiso calc PR 0.70 A 1
H H12B 0.4100 0.8722 1.2149 0.170 Uiso calc PR 0.70 A 1
H H12C 0.2554 0.7591 1.2190 0.170 Uiso calc PR 0.70 A 1
O O2' 0.143(3) 0.773(2) 0.904(2) 0.076(6) Uani d PU 0.30 A 2
O O3' 0.382(2) 0.760(2) 1.0313(15) 0.054(4) Uani d PDU 0.30 A 2
C C11' 0.271(3) 0.813(3) 1.135(2) 0.067(6) Uani d PDU 0.30 A 2
H H11C 0.3363 0.8111 1.2103 0.081 Uiso calc PR 0.30 A 2
H H11D 0.1766 0.7407 1.1605 0.081 Uiso calc PR 0.30 A 2
C C12' 0.199(6) 0.985(3) 1.087(4) 0.149(15) Uani d PDU 0.30 A 2
H H12D 0.1258 1.0196 1.1564 0.223 Uiso calc PR 0.30 A 2
H H12E 0.1324 0.9867 1.0137 0.223 Uiso calc PR 0.30 A 2
H H12F 0.2923 1.0569 1.0626 0.223 Uiso calc PR 0.30 A 2
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
N1 O1 C9 109.0(4)
C8 N1 O1 112.3(4)
C2 C1 Br1 110.5(4)
C2 C1 Br1' 112.8(6)
C2 C1 H1A 109.6
Br1 C1 H1A 109.6
Br1' C1 H1A 93.0
C2 C1 H1B 109.6
Br1 C1 H1B 109.6
Br1' C1 H1B 122.0
H1A C1 H1B 108.1
C7 C2 C3 117.9(6)
C7 C2 C1 121.8(5)
C3 C2 C1 120.2(5)
C4 C3 C2 120.1(6)
C4 C3 H3 119.9
C2 C3 H3 119.9
C5 C4 C3 122.3(6)
C5 C4 H4 118.9
C3 C4 H4 118.9
C4 C5 C6 118.7(6)
C4 C5 H5 120.7
C6 C5 H5 120.7
C7 C6 C5 120.5(6)
C7 C6 H6 119.8
C5 C6 H6 119.8
C6 C7 C2 120.5(5)
C6 C7 C8 119.4(5)
C2 C7 C8 120.2(5)
N1 C8 C10 115.9(5)
N1 C8 C7 126.3(5)
C10 C8 C7 117.7(5)
O1 C9 H9A 109.5
O1 C9 H9B 109.5
H9A C9 H9B 109.5
O1 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
O2 C10 O3 124.6(7)
O2' C10 O3 110.0(11)
O2 C10 O3' 115.1(9)
O2' C10 O3' 129.0(12)
O2 C10 C8 121.0(7)
O2' C10 C8 121.1(10)
O3 C10 C8 114.3(6)
O3' C10 C8 109.7(8)
C10 O3 C11 120.2(8)
O3 C11 C12 108.3(9)
O3 C11 H11A 110.0
C12 C11 H11A 110.0
O3 C11 H11B 110.0
C12 C11 H11B 110.0
H11A C11 H11B 108.4
C11 C12 H12A 109.5
C11 C12 H12B 109.5
H12A C12 H12B 109.5
C11 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C10 O3' C11' 113.9(15)
O3' C11' C12' 110(2)
O3' C11' H11C 109.7
C12' C11' H11C 109.7
O3' C11' H11D 109.7
C12' C11' H11D 109.7
H11C C11' H11D 108.2
C11' C12' H12D 109.5
C11' C12' H12E 109.5
H12D C12' H12E 109.5
C11' C12' H12F 109.5
H12D C12' H12F 109.5
H12E C12' H12F 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.936(6)
Br1' C1 1.952(9)
O1 N1 1.377(6)
O1 C9 1.429(7)
N1 C8 1.276(6)
C1 C2 1.446(8)
C1 H1A 0.9700
C1 H1B 0.9700
C2 C7 1.398(7)
C2 C3 1.407(7)
C3 C4 1.360(9)
C3 H3 0.9300
C4 C5 1.360(9)
C4 H4 0.9300
C5 C6 1.395(8)
C5 H5 0.9300
C6 C7 1.375(8)
C6 H6 0.9300
C7 C8 1.499(7)
C8 C10 1.494(8)
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C10 O2 1.231(10)
C10 O2' 1.268(19)
C10 O3 1.349(10)
C10 O3' 1.353(16)
O3 C11 1.443(8)
C11 C12 1.501(9)
C11 H11A 0.9700
C11 H11B 0.9700
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
O3' C11' 1.454(10)
C11' C12' 1.532(11)
C11' H11C 0.9700
C11' H11D 0.9700
C12' H12D 0.9600
C12' H12E 0.9600
C12' H12F 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
C9 H9C O2 1_655 0.96 2.59 3.264(10) 127.4
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
C9 O1 N1 C8 177.4(5)
Br1 C1 C2 C7 -87.3(6)
Br1' C1 C2 C7 -106.0(7)
Br1 C1 C2 C3 94.3(5)
Br1' C1 C2 C3 75.6(7)
C7 C2 C3 C4 0.1(8)
C1 C2 C3 C4 178.5(5)
C2 C3 C4 C5 -0.4(10)
C3 C4 C5 C6 0.9(10)
C4 C5 C6 C7 -1.1(10)
C5 C6 C7 C2 0.8(9)
C5 C6 C7 C8 -179.0(5)
C3 C2 C7 C6 -0.3(8)
C1 C2 C7 C6 -178.7(5)
C3 C2 C7 C8 179.5(5)
C1 C2 C7 C8 1.1(7)
O1 N1 C8 C10 -179.5(6)
O1 N1 C8 C7 3.3(8)
C6 C7 C8 N1 103.7(7)
C2 C7 C8 N1 -76.1(7)
C6 C7 C8 C10 -73.4(8)
C2 C7 C8 C10 106.8(7)
N1 C8 C10 O2 -159.6(8)
C7 C8 C10 O2 17.8(12)
N1 C8 C10 O2' 152.8(13)
C7 C8 C10 O2' -29.8(16)
N1 C8 C10 O3 17.4(10)
C7 C8 C10 O3 -165.1(7)
N1 C8 C10 O3' -21.9(12)
C7 C8 C10 O3' 155.5(10)
O2 C10 O3 C11 -6.2(15)
O2' C10 O3 C11 36.7(16)
O3' C10 O3 C11 -92.5(15)
C8 C10 O3 C11 176.9(8)
C10 O3 C11 C12 96.9(12)
O2 C10 O3' C11' -30(2)
O2' C10 O3' C11' 15(3)
O3 C10 O3' C11' 84.8(19)
C8 C10 O3' C11' -170.6(14)
C10 O3' C11' C12' -71(3)
