#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/74/2227484.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227484
loop_
_publ_author_name
'Yang, Qian-Jiao'
'Liu, Dan'
'Zuo, Jian'
'Hu, Guo-Dong'
'Zhao, Lin-Xiang'
_publ_section_title
;
 Ethyl 2-[(Z)-2-benzylhydrazin-1-ylidene]-2-bromoacetate
;
_journal_coeditor_code           HB5585
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2334
_journal_paper_doi               10.1107/S1600536810032071
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C11 H13 Br N2 O2'
_chemical_formula_moiety         'C11 H13 Br N2 O2'
_chemical_formula_sum            'C11 H13 Br N2 O2'
_chemical_formula_weight         285.14
_chemical_name_systematic
;
Ethyl 2-[(Z)-2-benzylhydrazin-1-ylidene]-2-bromoacetate
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.935(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0460(10)
_cell_length_b                   11.2350(10)
_cell_length_c                   12.326(2)
_cell_measurement_reflns_used    1479
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      24.83
_cell_measurement_theta_min      2.25
_cell_volume                     1251.1(3)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX CCD'
_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  0.0194
_diffrn_reflns_av_sigmaI/netI    0.0294
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            4952
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    3.274
_exptl_absorpt_correction_T_max  0.803
_exptl_absorpt_correction_T_min  0.495
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Siemens, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.607
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2188
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0375
_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)+(0.0656P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1114
_reflns_number_gt                1475
_reflns_number_total             2188
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5585.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2227484
_cod_database_fobs_code          2227484
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.44688(4) 0.25237(4) 0.31304(3) 0.0668(2) Uani d . 1 . .
O O1 0.3161(3) 0.0317(2) 0.2073(2) 0.0755(8) Uani d . 1 . .
O O2 0.3458(2) 0.0749(2) 0.03230(18) 0.0534(6) Uani d . 1 . .
N N1 0.5769(3) 0.3675(3) 0.1176(2) 0.0501(7) Uani d . 1 . .
H H1 0.5721 0.3973 0.1815 0.060 Uiso calc R 1 . .
N N2 0.5071(3) 0.2673(2) 0.0922(2) 0.0424(7) Uani d . 1 . .
C C1 0.8144(3) 0.3760(3) 0.0231(3) 0.0436(8) Uani d . 1 . .
C C2 0.8605(4) 0.3447(4) -0.0771(3) 0.0726(11) Uani d . 1 . .
H H2 0.7946 0.3505 -0.1374 0.087 Uiso calc R 1 . .
C C3 1.0035(5) 0.3045(4) -0.0906(4) 0.0852(13) Uani d . 1 . .
H H3 1.0321 0.2834 -0.1594 0.102 Uiso calc R 1 . .
C C4 1.1013(4) 0.2958(4) -0.0045(4) 0.0696(11) Uani d . 1 . .
H H4 1.1976 0.2700 -0.0136 0.083 Uiso calc R 1 . .
C C5 1.0569(4) 0.3253(4) 0.0954(4) 0.0830(13) Uani d . 1 . .
H H5 1.1234 0.3182 0.1551 0.100 Uiso calc R 1 . .
C C6 0.9142(4) 0.3659(4) 0.1105(3) 0.0721(11) Uani d . 1 . .
H H6 0.8863 0.3862 0.1797 0.087 Uiso calc R 1 . .
C C7 0.6617(3) 0.4268(3) 0.0367(3) 0.0475(8) Uani d . 1 . .
H H7A 0.6717 0.5101 0.0563 0.057 Uiso calc R 1 . .
H H7B 0.6064 0.4228 -0.0327 0.057 Uiso calc R 1 . .
C C8 0.4424(3) 0.2069(3) 0.1640(3) 0.0432(7) Uani d . 1 . .
C C9 0.3625(3) 0.0958(3) 0.1382(3) 0.0508(8) Uani d . 1 . .
C C10 0.2617(4) -0.0317(4) 0.0018(3) 0.0722(11) Uani d . 1 . .
H H10A 0.1758 -0.0378 0.0454 0.087 Uiso calc R 1 . .
H H10B 0.3226 -0.1017 0.0151 0.087 Uiso calc R 1 . .
C C11 0.2142(5) -0.0254(4) -0.1139(3) 0.0950(15) Uani d . 1 . .
H H11A 0.1489 0.0412 -0.1259 0.142 Uiso calc R 1 . .
H H11B 0.1632 -0.0974 -0.1349 0.142 Uiso calc R 1 . .
H H11C 0.2993 -0.0159 -0.1565 0.142 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 O2 C10 . . 115.5(3) ?
N2 N1 C7 . . 119.5(3) ?
N2 N1 H1 . . 120.2 ?
C7 N1 H1 . . 120.2 ?
C8 N2 N1 . . 121.2(3) ?
C2 C1 C6 . . 117.9(3) ?
C2 C1 C7 . . 121.2(3) ?
C6 C1 C7 . . 120.7(3) ?
C1 C2 C3 . . 121.3(4) ?
C1 C2 H2 . . 119.4 ?
C3 C2 H2 . . 119.4 ?
C4 C3 C2 . . 120.5(4) ?
C4 C3 H3 . . 119.7 ?
C2 C3 H3 . . 119.7 ?
C3 C4 C5 . . 118.9(4) ?
C3 C4 H4 . . 120.6 ?
C5 C4 H4 . . 120.6 ?
C4 C5 C6 . . 121.5(4) ?
C4 C5 H5 . . 119.3 ?
C6 C5 H5 . . 119.3 ?
C1 C6 C5 . . 119.9(4) ?
C1 C6 H6 . . 120.1 ?
C5 C6 H6 . . 120.1 ?
N1 C7 C1 . . 114.9(3) ?
N1 C7 H7A . . 108.5 ?
C1 C7 H7A . . 108.5 ?
N1 C7 H7B . . 108.5 ?
C1 C7 H7B . . 108.5 ?
H7A C7 H7B . . 107.5 ?
N2 C8 C9 . . 122.6(3) ?
N2 C8 Br1 . . 122.4(3) ?
C9 C8 Br1 . . 115.0(2) ?
O1 C9 O2 . . 124.2(3) ?
O1 C9 C8 . . 122.7(3) ?
O2 C9 C8 . . 113.1(3) ?
O2 C10 C11 . . 109.5(3) ?
O2 C10 H10A . . 109.8 ?
C11 C10 H10A . . 109.8 ?
O2 C10 H10B . . 109.8 ?
C11 C10 H10B . . 109.8 ?
H10A C10 H10B . . 108.2 ?
C10 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C10 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 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
Br1 C8 . 1.906(3) ?
O1 C9 . 1.207(4) ?
O2 C9 . 1.328(4) ?
O2 C10 . 1.457(4) ?
N1 N2 . 1.320(3) ?
N1 C7 . 1.451(4) ?
N1 H1 . 0.8600 ?
N2 C8 . 1.280(4) ?
C1 C2 . 1.370(4) ?
C1 C6 . 1.374(5) ?
C1 C7 . 1.512(4) ?
C2 C3 . 1.388(5) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.350(6) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.355(6) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.391(5) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C9 . 1.468(5) ?
C10 C11 . 1.470(5) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 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
N1 H1 O1 2_655 0.86 2.24 2.965(4) 141
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745779
