#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:52:34 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180320 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/34/7153454.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_7153454
loop_
_publ_author_name
'Leng, Dong-Hui'
'Wang, De-Xian'
'Huang, Zhi-Tang'
'Wang, Mei-Xiang'
_publ_section_title
;
 Highly efficient and enantioselective biotransformations of β-lactam
 carbonitriles and carboxamides and their synthetic applications.
;
_journal_issue                   20
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4736
_journal_page_last               4743
_journal_paper_doi               10.1039/c0ob00198h
_journal_volume                  8
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_sum            'C11 H11 Br N2 O2'
_chemical_formula_weight         283.13
_chemical_name_systematic
;
?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 93.749(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.753(3)
_cell_length_b                   12.723(7)
_cell_length_c                   9.586(6)
_cell_measurement_reflns_used    2213
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      2.1
_cell_volume                     578.4(6)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      160(2)
_diffrn_detector_area_resol_mean 14.63
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1445
_diffrn_reflns_av_sigmaI/netI    0.1310
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5973
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    3.540
_exptl_absorpt_correction_T_max  0.8714
_exptl_absorpt_correction_T_min  0.2706
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   CrystalClear
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.713
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.084
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.014(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         2034
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      0.974
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0523
_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)+(0.0100P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.0913
_reflns_number_gt                1557
_reflns_number_total             2034
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ob00198h.txt
_cod_data_source_block           m100106f
_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 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        578.5(6)
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7153454
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 0.37391(11) -0.09482(5) -0.27033(5) 0.0463(2) Uani 1 1 d .
O1 O 1.1193(6) -0.1157(4) 0.2598(3) 0.0285(11) Uani 1 1 d .
O2 O 1.1433(6) 0.1814(3) 0.4560(4) 0.0272(9) Uani 1 1 d .
N1 N 0.7180(8) 0.2238(4) 0.5287(4) 0.0218(10) Uani 1 1 d D
N2 N 0.9211(7) 0.0524(3) 0.2458(4) 0.0178(9) Uani 1 1 d .
C1 C 0.9740(10) -0.0448(5) 0.2990(5) 0.0200(11) Uani 1 1 d .
C2 C 0.7856(9) -0.0264(4) 0.4185(5) 0.0220(11) Uani 1 1 d .
H2A H 0.8850 -0.0289 0.5125 0.026 Uiso 1 1 calc R
H2B H 0.6125 -0.0699 0.4142 0.026 Uiso 1 1 calc R
C3 C 0.7431(9) 0.0869(4) 0.3575(5) 0.0181(11) Uani 1 1 d .
H3 H 0.5442 0.1038 0.3248 0.022 Uiso 1 1 calc R
C4 C 0.8859(9) 0.1702(4) 0.4518(5) 0.0179(11) Uani 1 1 d .
C5 C 1.0170(9) 0.1057(4) 0.1236(5) 0.0204(11) Uani 1 1 d .
H5A H 1.1809 0.0676 0.0899 0.024 Uiso 1 1 calc R
H5B H 1.0794 0.1776 0.1501 0.024 Uiso 1 1 calc R
C6 C 0.7877(9) 0.1121(4) 0.0071(5) 0.0200(11) Uani 1 1 d .
C7 C 0.6586(10) 0.2071(5) -0.0299(5) 0.0267(12) Uani 1 1 d .
H7 H 0.7196 0.2699 0.0165 0.032 Uiso 1 1 calc R
C8 C 0.4441(10) 0.2110(5) -0.1327(5) 0.0311(13) Uani 1 1 d .
H8 H 0.3588 0.2767 -0.1565 0.037 Uiso 1 1 calc R
C9 C 0.3506(9) 0.1225(5) -0.2015(5) 0.0304(13) Uani 1 1 d .
H9 H 0.1986 0.1253 -0.2709 0.036 Uiso 1 1 calc R
C10 C 0.4855(10) 0.0276(4) -0.1667(5) 0.0254(12) Uani 1 1 d .
C11 C 0.6993(9) 0.0220(4) -0.0636(5) 0.0220(12) Uani 1 1 d .
H11 H 0.7863 -0.0436 -0.0410 0.026 Uiso 1 1 calc R
H1A H 0.532(3) 0.213(4) 0.529(5) 0.038(16) Uiso 1 1 d D
H1B H 0.789(6) 0.264(3) 0.599(3) 0.018(14) Uiso 1 1 d D
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0664(4) 0.0472(4) 0.0240(3) -0.0027(4) -0.0077(2) -0.0246(4)
O1 0.0369(19) 0.020(3) 0.027(2) -0.0037(18) -0.0059(16) 0.0077(17)
O2 0.0126(17) 0.039(2) 0.030(2) -0.0117(18) -0.0028(15) -0.0046(16)
N1 0.015(2) 0.029(3) 0.021(3) -0.008(2) -0.0028(18) 0.001(2)
N2 0.021(2) 0.021(2) 0.012(2) 0.0003(18) -0.0004(17) 0.0043(18)
C1 0.018(3) 0.022(3) 0.019(3) 0.001(2) -0.008(2) -0.001(2)
C2 0.022(2) 0.023(3) 0.020(3) 0.003(2) -0.003(2) -0.007(2)
C3 0.015(2) 0.024(3) 0.015(3) -0.001(2) -0.001(2) 0.003(2)
C4 0.017(3) 0.021(3) 0.015(3) 0.005(2) -0.006(2) 0.001(2)
C5 0.021(2) 0.021(3) 0.019(3) 0.004(2) -0.001(2) 0.004(2)
C6 0.020(2) 0.026(3) 0.015(3) 0.003(2) 0.005(2) -0.003(2)
C7 0.032(3) 0.025(3) 0.023(3) 0.007(2) 0.002(2) 0.004(3)
C8 0.034(3) 0.033(3) 0.025(3) 0.014(3) -0.001(2) 0.006(3)
C9 0.023(3) 0.050(4) 0.017(3) 0.013(3) -0.008(2) -0.004(3)
C10 0.028(3) 0.036(3) 0.012(3) 0.002(2) -0.002(2) -0.013(3)
C11 0.026(2) 0.022(3) 0.018(3) 0.001(2) 0.000(2) 0.002(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
C4 N1 H1A 124(3)
C4 N1 H1B 120(2)
H1A N1 H1B 114.4(17)
C1 N2 C5 132.0(4)
C1 N2 C3 95.7(4)
C5 N2 C3 132.2(4)
O1 C1 N2 131.2(5)
O1 C1 C2 136.5(5)
N2 C1 C2 92.3(4)
C1 C2 C3 85.9(4)
C1 C2 H2A 114.3
C3 C2 H2A 114.3
C1 C2 H2B 114.3
C3 C2 H2B 114.3
H2A C2 H2B 111.5
N2 C3 C4 112.6(4)
N2 C3 C2 86.0(3)
C4 C3 C2 112.2(4)
N2 C3 H3 114.3
C4 C3 H3 114.3
C2 C3 H3 114.3
O2 C4 N1 124.2(5)
O2 C4 C3 120.3(4)
N1 C4 C3 115.5(4)
N2 C5 C6 111.8(4)
N2 C5 H5A 109.2
C6 C5 H5A 109.2
N2 C5 H5B 109.2
C6 C5 H5B 109.2
H5A C5 H5B 107.9
C11 C6 C7 118.7(5)
C11 C6 C5 120.0(5)
C7 C6 C5 121.3(5)
C8 C7 C6 120.6(6)
C8 C7 H7 119.7
C6 C7 H7 119.7
C9 C8 C7 121.4(6)
C9 C8 H8 119.3
C7 C8 H8 119.3
C8 C9 C10 117.9(5)
C8 C9 H9 121.1
C10 C9 H9 121.1
C11 C10 C9 121.6(5)
C11 C10 Br1 120.0(4)
C9 C10 Br1 118.3(4)
C10 C11 C6 119.8(5)
C10 C11 H11 120.1
C6 C11 H11 120.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C10 1.904(5)
O1 C1 1.210(7)
O2 C4 1.230(5)
N1 C4 1.312(6)
N1 H1A 0.894(10)
N1 H1B 0.895(10)
N2 C1 1.355(7)
N2 C5 1.452(6)
N2 C3 1.475(6)
C1 C2 1.518(7)
C2 C3 1.565(7)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C4 1.523(7)
C3 H3 1.0000
C5 C6 1.511(6)
C5 H5A 0.9900
C5 H5B 0.9900
C6 C11 1.383(7)
C6 C7 1.392(7)
C7 C8 1.372(7)
C7 H7 0.9500
C8 C9 1.365(8)
C8 H8 0.9500
C9 C10 1.396(7)
C9 H9 0.9500
C10 C11 1.372(7)
C11 H11 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O2 0.894(10) 1.974(16) 2.826(5) 159(4) 1_455
N1 H1B O1 0.895(10) 2.069(16) 2.945(6) 166(4) 2_756
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
C5 N2 C1 O1 0.5(9)
C3 N2 C1 O1 -177.3(5)
C5 N2 C1 C2 -179.4(5)
C3 N2 C1 C2 2.8(4)
O1 C1 C2 C3 177.5(6)
N2 C1 C2 C3 -2.7(4)
C1 N2 C3 C4 109.6(4)
C5 N2 C3 C4 -68.1(6)
C1 N2 C3 C2 -2.8(4)
C5 N2 C3 C2 179.5(5)
C1 C2 C3 N2 2.5(3)
C1 C2 C3 C4 -110.3(4)
N2 C3 C4 O2 -19.5(6)
C2 C3 C4 O2 75.6(5)
N2 C3 C4 N1 162.9(4)
C2 C3 C4 N1 -102.1(5)
C1 N2 C5 C6 105.6(6)
C3 N2 C5 C6 -77.5(6)
N2 C5 C6 C11 -69.7(6)
N2 C5 C6 C7 109.3(5)
C11 C6 C7 C8 1.3(7)
C5 C6 C7 C8 -177.8(4)
C6 C7 C8 C9 0.1(7)
C7 C8 C9 C10 -1.7(7)
C8 C9 C10 C11 2.1(7)
C8 C9 C10 Br1 -175.9(4)
C9 C10 C11 C6 -0.8(7)
Br1 C10 C11 C6 177.2(3)
C7 C6 C11 C10 -0.9(6)
C5 C6 C11 C10 178.2(4)
