#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/26/2212611.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_2212611
loop_
_publ_author_name
'Xi-Zhao Wang'
'Li-Na Pang'
'Jun-Zhi Liu'
'Fang-Gang Sun'
'Jian-Wu Wang'
_publ_section_title
;
 Benzyl 6,6-dibromo-2β-chloromethyl-2α-methylpenicillanate
;
_journal_coeditor_code           IM2001
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1184
_journal_page_last               o1185
_journal_paper_doi               10.1107/S1600536807004606
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C15 H14 Br2 Cl N O3 S'
_chemical_formula_moiety         'C15 H14 Br2 Cl N O3 S'
_chemical_formula_sum            'C15 H14 Br2 Cl N O3 S'
_chemical_formula_weight         483.60
_chemical_name_systematic
;
Benzyl 6,6-dibromo-2β-chloromethyl-2α-methylpenicillanate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.35220(10)
_cell_length_b                   15.6712(2)
_cell_length_c                   17.9940(2)
_cell_measurement_reflns_used    7637
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.30
_cell_measurement_theta_min      2.26
_cell_volume                     1791.24(4)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        APEX2
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker 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  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0369
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            18951
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.72
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.803
_exptl_absorpt_correction_T_max  0.6325
_exptl_absorpt_correction_T_min  0.2797
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(APEX2; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.793
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.256
_refine_ls_abs_structure_details 'Flack (1983), with 1719 Friedel pairs'
_refine_ls_abs_structure_Flack   0.017(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         4083
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0246
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0218P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0535
_refine_ls_wR_factor_ref         0.0553
_reflns_number_gt                3551
_reflns_number_total             4083
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            im2001.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 'Orthorhombic' changed to
'orthorhombic' 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               2212611
_cod_database_fobs_code          2212611
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
Br Br1 0.60805(5) 0.40400(2) 0.628296(17) 0.05570(10) Uani d . 1
Br Br2 0.99515(5) 0.485181(17) 0.71633(2) 0.05961(10) Uani d . 1
C C1 0.8656(10) -0.1177(3) 1.0105(3) 0.1032(15) Uani d U 1
H H1 0.9639 -0.1591 0.9975 0.124 Uiso calc R 1
C C2 0.6809(10) -0.1406(3) 1.0404(2) 0.0922(13) Uani d U 1
H H2 0.6506 -0.1983 1.0458 0.111 Uiso calc R 1
C C3 0.5408(8) -0.0840(3) 1.0624(2) 0.0929(13) Uani d U 1
H H3 0.4167 -0.1017 1.0851 0.112 Uiso calc R 1
C C4 0.5803(7) 0.0030(3) 1.05142(19) 0.0736(10) Uani d . 1
H H4 0.4806 0.0434 1.0654 0.088 Uiso calc R 1
C C5 0.7651(5) 0.02819(17) 1.02011(15) 0.0478(7) Uani d . 1
C C6 0.9097(8) -0.0311(2) 0.9990(2) 0.0825(13) Uani d . 1
H H6 1.0359 -0.0144 0.9772 0.099 Uiso calc R 1
C C7 0.8089(6) 0.12103(17) 1.00641(16) 0.0566(8) Uani d . 1
H H7A 0.7106 0.1563 1.0340 0.068 Uiso calc R 1
H H7B 0.9508 0.1353 1.0220 0.068 Uiso calc R 1
C C8 0.7815(4) 0.21501(15) 0.90397(15) 0.0369(6) Uani d . 1
C C9 0.7415(4) 0.21846(14) 0.82062(14) 0.0322(5) Uani d . 1
H H9 0.8086 0.1691 0.7971 0.039 Uiso calc R 1
C C10 0.5019(4) 0.21874(13) 0.80057(14) 0.0341(5) Uani d . 1
C C11 0.3591(5) 0.17379(17) 0.85646(17) 0.0471(7) Uani d . 1
H H11A 0.2153 0.1788 0.8407 0.071 Uiso calc R 1
H H11B 0.3753 0.1998 0.9044 0.071 Uiso calc R 1
H H11C 0.3970 0.1146 0.8594 0.071 Uiso calc R 1
C C12 0.4693(4) 0.18451(15) 0.72219(15) 0.0421(6) Uani d . 1
H H12A 0.5537 0.2175 0.6877 0.051 Uiso calc R 1
H H12B 0.3226 0.1913 0.7084 0.051 Uiso calc R 1
C C13 0.6937(4) 0.37177(13) 0.78891(15) 0.0349(5) Uani d . 1
H H13 0.7319 0.4128 0.8277 0.042 Uiso calc R 1
C C14 0.7930(4) 0.39435(15) 0.71165(14) 0.0384(5) Uani d . 1
C C15 0.9000(4) 0.30635(14) 0.71728(15) 0.0360(5) Uani d . 1
Cl Cl1 0.54073(12) 0.07348(4) 0.71496(5) 0.05441(19) Uani d . 1
N N8 0.8294(3) 0.29592(12) 0.78919(12) 0.0334(4) Uani d . 1
O O1 0.7842(4) 0.13503(11) 0.92626(10) 0.0470(5) Uani d . 1
O O2 0.8066(4) 0.27665(12) 0.94281(11) 0.0551(5) Uani d . 1
O O3 0.9998(4) 0.26154(12) 0.67690(11) 0.0505(5) Uani d . 1
S S1 0.42737(10) 0.33321(4) 0.79851(4) 0.04049(16) Uani 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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
_geom_angle_publ_flag
C2 C1 C6 119.6(5) ?
C2 C1 H1 120.2 ?
C6 C1 H1 120.2 ?
C3 C2 C1 122.2(4) ?
C3 C2 H2 118.9 ?
C1 C2 H2 118.9 ?
C2 C3 C4 119.5(4) ?
C2 C3 H3 120.3 ?
C4 C3 H3 120.3 ?
C5 C4 C3 119.7(4) ?
C5 C4 H4 120.2 ?
C3 C4 H4 120.2 ?
C6 C5 C4 120.0(3) ?
C6 C5 C7 119.4(3) ?
C4 C5 C7 120.6(3) ?
C5 C6 C1 119.0(5) ?
C5 C6 H6 120.5 ?
C1 C6 H6 120.5 ?
O1 C7 C5 106.6(2) ?
O1 C7 H7A 110.4 ?
C5 C7 H7A 110.4 ?
O1 C7 H7B 110.4 ?
C5 C7 H7B 110.4 ?
H7A C7 H7B 108.6 ?
O2 C8 O1 125.9(2) ?
O2 C8 C9 124.5(2) ?
O1 C8 C9 109.6(2) ?
N8 C9 C8 110.5(2) ?
N8 C9 C10 106.38(19) ?
C8 C9 C10 112.9(2) ?
N8 C9 H9 109.0 ?
C8 C9 H9 109.0 ?
C10 C9 H9 109.0 ?
C12 C10 C11 111.5(2) ?
C12 C10 C9 110.2(2) ?
C11 C10 C9 115.2(2) ?
C12 C10 S1 106.69(16) ?
C11 C10 S1 107.91(17) ?
C9 C10 S1 104.81(15) ?
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 ?
C10 C12 Cl1 111.86(17) ?
C10 C12 H12A 109.2 ?
Cl1 C12 H12A 109.2 ?
C10 C12 H12B 109.2 ?
Cl1 C12 H12B 109.2 ?
H12A C12 H12B 107.9 ?
N8 C13 C14 87.10(18) ?
N8 C13 S1 106.19(15) ?
C14 C13 S1 122.53(18) ?
N8 C13 H13 112.6 ?
C14 C13 H13 112.6 ?
S1 C13 H13 112.6 ?
C15 C14 C13 85.25(18) ?
C15 C14 Br1 113.17(17) ?
C13 C14 Br1 117.83(18) ?
C15 C14 Br2 111.45(17) ?
C13 C14 Br2 113.45(16) ?
Br1 C14 Br2 112.77(12) ?
O3 C15 N8 132.4(2) ?
O3 C15 C14 136.2(3) ?
N8 C15 C14 91.4(2) ?
C15 N8 C9 126.2(2) yes
C15 N8 C13 95.26(19) yes
C9 N8 C13 116.93(19) yes
C8 O1 C7 116.3(2) ?
C13 S1 C10 94.96(11) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C14 1.911(3) yes
Br2 C14 1.919(2) yes
C1 C2 1.339(7) ?
C1 C6 1.402(6) ?
C1 H1 0.9300 ?
C2 C3 1.318(7) ?
C2 H2 0.9300 ?
C3 C4 1.400(6) ?
C3 H3 0.9300 ?
C4 C5 1.361(5) ?
C4 H4 0.9300 ?
C5 C6 1.360(5) ?
C5 C7 1.502(4) ?
C6 H6 0.9300 ?
C7 O1 1.467(3) ?
C7 H7A 0.9700 ?
C7 H7B 0.9700 ?
C8 O2 1.203(3) ?
C8 O1 1.316(3) ?
C8 C9 1.522(4) ?
C9 N8 1.451(3) yes
C9 C10 1.564(4) ?
C9 H9 0.9800 ?
C10 C12 1.523(3) ?
C10 C11 1.527(4) ?
C10 S1 1.856(2) yes
C11 H11A 0.9600 ?
C11 H11B 0.9600 ?
C11 H11C 0.9600 ?
C12 Cl1 1.803(2) ?
C12 H12A 0.9700 ?
C12 H12B 0.9700 ?
C13 N8 1.468(3) yes
C13 C14 1.567(4) ?
C13 S1 1.805(3) yes
C13 H13 0.9800 ?
C14 C15 1.541(3) ?
C15 O3 1.193(3) ?
C15 N8 1.379(3) 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
C6 C1 C2 C3 -2.8(8)
C1 C2 C3 C4 3.0(7)
C2 C3 C4 C5 -1.9(6)
C3 C4 C5 C6 0.7(5)
C3 C4 C5 C7 178.8(3)
C4 C5 C6 C1 -0.5(6)
C7 C5 C6 C1 -178.6(4)
C2 C1 C6 C5 1.5(7)
C6 C5 C7 O1 73.2(4)
C4 C5 C7 O1 -104.9(3)
O2 C8 C9 N8 26.0(4)
O1 C8 C9 N8 -154.0(2)
O2 C8 C9 C10 -93.0(3)
O1 C8 C9 C10 87.0(3)
N8 C9 C10 C12 82.9(2)
C8 C9 C10 C12 -155.75(19)
N8 C9 C10 C11 -149.9(2)
C8 C9 C10 C11 -28.6(3)
N8 C9 C10 S1 -31.5(2)
C8 C9 C10 S1 89.8(2)
C11 C10 C12 Cl1 -63.5(3)
C9 C10 C12 Cl1 65.6(2)
S1 C10 C12 Cl1 178.86(14)
N8 C13 C14 C15 6.97(17)
S1 C13 C14 C15 -100.42(19)
N8 C13 C14 Br1 120.71(17)
S1 C13 C14 Br1 13.3(3)
N8 C13 C14 Br2 -104.38(17)
S1 C13 C14 Br2 148.23(13)
C13 C14 C15 O3 170.7(3)
Br1 C14 C15 O3 52.4(4)
Br2 C14 C15 O3 -76.0(4)
C13 C14 C15 N8 -7.41(18)
Br1 C14 C15 N8 -125.70(18)
Br2 C14 C15 N8 105.94(19)
O3 C15 N8 C9 -41.2(4)
C14 C15 N8 C9 137.0(2)
O3 C15 N8 C13 -170.3(3)
C14 C15 N8 C13 7.92(19)
C8 C9 N8 C15 152.0(2)
C10 C9 N8 C15 -85.1(3)
C8 C9 N8 C13 -88.1(3)
C10 C9 N8 C13 34.9(3)
C14 C13 N8 C15 -7.79(19)
S1 C13 N8 C15 115.30(18)
C14 C13 N8 C9 -143.1(2)
S1 C13 N8 C9 -20.0(3)
O2 C8 O1 C7 3.5(4)
C9 C8 O1 C7 -176.5(3)
C5 C7 O1 C8 169.1(3)
N8 C13 S1 C10 -1.12(18)
C14 C13 S1 C10 95.93(19)
C12 C10 S1 C13 -97.96(19)
C11 C10 S1 C13 142.10(19)
C9 C10 S1 C13 18.90(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21185480
