#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:45:47 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180314 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/28/7152823.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_7152823
loop_
_publ_author_name
'De Fusco, Claudia'
'Meninno, Sara'
'Tedesco, Consiglia'
'Lattanzi, Alessandra'
_publ_section_title
;
 Enantioselective α-hydroxylation of β-ketoamides.
;
_journal_issue                   6
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              896
_journal_page_last               899
_journal_paper_doi               10.1039/c2ob27283k
_journal_volume                  11
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H12 Br N O3'
_chemical_formula_sum            'C16 H12 Br N O3'
_chemical_formula_weight         346.18
_chemical_name_systematic
;
?
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.801(3)
_cell_length_b                   10.969(3)
_cell_length_c                   14.070(4)
_cell_measurement_reflns_used    9915
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.6982
_cell_measurement_theta_min      1.4472
_cell_volume                     1512.6(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_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  0.0979
_diffrn_reflns_av_sigmaI/netI    0.0707
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18126
_diffrn_reflns_theta_full        28.06
_diffrn_reflns_theta_max         28.06
_diffrn_reflns_theta_min         2.35
_exptl_absorpt_coefficient_mu    2.726
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.2456
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.851
_refine_diff_density_min         -0.927
_refine_diff_density_rms         0.090
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.018(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3466
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.1224
_refine_ls_R_factor_gt           0.0789
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1777
_refine_ls_wR_factor_ref         0.1993
_reflns_number_gt                2339
_reflns_number_total             3466
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob27283k.txt
_cod_data_source_block           smd250_6c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_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_database_code               7152823
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
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 0.13762(9) 0.36060(8) 0.22125(5) 0.0861(4) Uani 1 1 d .
O1 O 0.4575(4) 0.3342(4) 0.5579(3) 0.0604(11) Uani 1 1 d .
H1 H 0.5153 0.3328 0.5158 0.091 Uiso 1 1 calc R
O2 O 0.4212(5) 0.0710(5) 0.5562(3) 0.0775(14) Uani 1 1 d .
O3 O 0.1156(5) 0.2465(5) 0.5898(3) 0.0718(13) Uani 1 1 d .
N1 N 0.2774(5) 0.3193(5) 0.6880(3) 0.0553(13) Uani 1 1 d .
H1A H 0.3603 0.3451 0.6883 0.066 Uiso 1 1 calc R
C1 C 0.1992(7) 0.2164(6) 0.2797(5) 0.0589(15) Uani 1 1 d .
C2 C 0.1827(7) 0.1079(7) 0.2341(5) 0.0708(19) Uani 1 1 d .
H2 H 0.1414 0.1057 0.1746 0.085 Uiso 1 1 calc R
C3 C 0.2271(10) 0.0003(8) 0.2761(6) 0.090(2) Uani 1 1 d .
H3 H 0.2162 -0.0736 0.2445 0.108 Uiso 1 1 calc R
C4 C 0.2882(9) 0.0032(7) 0.3655(5) 0.077(2) Uani 1 1 d .
H4 H 0.3200 -0.0677 0.3940 0.093 Uiso 1 1 calc R
C5 C 0.2999(6) 0.1132(6) 0.4100(4) 0.0554(15) Uani 1 1 d .
C6 C 0.2573(6) 0.2205(5) 0.3703(4) 0.0479(13) Uani 1 1 d .
C7 C 0.2797(6) 0.3297(5) 0.4310(4) 0.0491(14) Uani 1 1 d .
H7A H 0.1946 0.3724 0.4422 0.059 Uiso 1 1 calc R
H7B H 0.3439 0.3853 0.4014 0.059 Uiso 1 1 calc R
C8 C 0.3386(6) 0.2776(6) 0.5256(4) 0.0496(14) Uani 1 1 d .
C9 C 0.3622(6) 0.1402(6) 0.5049(4) 0.0564(14) Uani 1 1 d .
C10 C 0.2326(6) 0.2804(6) 0.6046(4) 0.0487(14) Uani 1 1 d .
C11 C 0.2086(6) 0.3250(6) 0.7779(4) 0.0558(14) Uani 1 1 d .
C12 C 0.2872(7) 0.3367(7) 0.8588(4) 0.0654(19) Uani 1 1 d .
H12 H 0.3817 0.3410 0.8538 0.078 Uiso 1 1 calc R
C13 C 0.2267(8) 0.3422(8) 0.9462(4) 0.072(2) Uani 1 1 d .
H13 H 0.2807 0.3489 1.0003 0.086 Uiso 1 1 calc R
C14 C 0.0900(9) 0.3379(9) 0.9552(5) 0.086(2) Uani 1 1 d .
H14 H 0.0495 0.3425 1.0149 0.103 Uiso 1 1 calc R
C15 C 0.0124(9) 0.3268(15) 0.8759(5) 0.125(5) Uani 1 1 d .
H15 H -0.0820 0.3233 0.8819 0.150 Uiso 1 1 calc R
C16 C 0.0710(8) 0.3206(11) 0.7849(5) 0.104(3) Uani 1 1 d .
H16 H 0.0167 0.3138 0.7310 0.125 Uiso 1 1 calc R
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
C8 O1 H1 109.5
C10 N1 C11 129.7(5)
C10 N1 H1A 115.1
C11 N1 H1A 115.1
C2 C1 C6 120.4(7)
C2 C1 Br1 119.4(5)
C6 C1 Br1 120.1(5)
C1 C2 C3 120.4(6)
C1 C2 H2 119.8
C3 C2 H2 119.8
C2 C3 C4 119.9(7)
C2 C3 H3 120.1
C4 C3 H3 120.1
C5 C4 C3 118.1(7)
C5 C4 H4 120.9
C3 C4 H4 120.9
C6 C5 C4 123.2(6)
C6 C5 C9 108.6(5)
C4 C5 C9 128.2(6)
C5 C6 C1 118.0(6)
C5 C6 C7 114.4(5)
C1 C6 C7 127.6(6)
C6 C7 C8 104.5(5)
C6 C7 H7A 110.9
C8 C7 H7A 110.9
C6 C7 H7B 110.9
C8 C7 H7B 110.9
H7A C7 H7B 108.9
O1 C8 C10 108.9(4)
O1 C8 C9 111.6(5)
C10 C8 C9 105.0(5)
O1 C8 C7 115.1(5)
C10 C8 C7 111.3(5)
C9 C8 C7 104.5(4)
O2 C9 C5 127.6(6)
O2 C9 C8 125.1(6)
C5 C9 C8 107.4(5)
O3 C10 N1 124.1(5)
O3 C10 C8 120.6(5)
N1 C10 C8 115.3(5)
C16 C11 C12 120.0(6)
C16 C11 N1 122.1(6)
C12 C11 N1 117.9(5)
C13 C12 C11 120.2(6)
C13 C12 H12 119.9
C11 C12 H12 119.9
C14 C13 C12 121.1(6)
C14 C13 H13 119.5
C12 C13 H13 119.5
C13 C14 C15 118.9(7)
C13 C14 H14 120.6
C15 C14 H14 120.6
C14 C15 C16 121.7(8)
C14 C15 H15 119.2
C16 C15 H15 119.2
C11 C16 C15 118.2(7)
C11 C16 H16 120.9
C15 C16 H16 120.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.882(7)
O1 C8 1.396(7)
O1 H1 0.8200
O2 C9 1.196(7)
O3 C10 1.223(7)
N1 C10 1.323(7)
N1 C11 1.435(8)
N1 H1A 0.8600
C1 C2 1.362(9)
C1 C6 1.397(9)
C2 C3 1.390(11)
C2 H2 0.9300
C3 C4 1.393(11)
C3 H3 0.9300
C4 C5 1.364(10)
C4 H4 0.9300
C5 C6 1.368(9)
C5 C9 1.498(8)
C6 C7 1.487(8)
C7 C8 1.560(7)
C7 H7A 0.9700
C7 H7B 0.9700
C8 C10 1.522(8)
C8 C9 1.553(9)
C11 C16 1.353(10)
C11 C12 1.381(8)
C12 C13 1.366(9)
C12 H12 0.9300
C13 C14 1.346(11)
C13 H13 0.9300
C14 C15 1.356(11)
C14 H14 0.9300
C15 C16 1.405(11)
C15 H15 0.9300
C16 H16 0.9300
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 -1.9(11)
Br1 C1 C2 C3 -179.9(6)
C1 C2 C3 C4 0.4(12)
C2 C3 C4 C5 1.2(13)
C3 C4 C5 C6 -1.4(12)
C3 C4 C5 C9 -179.3(7)
C4 C5 C6 C1 -0.1(10)
C9 C5 C6 C1 178.2(5)
C4 C5 C6 C7 180.0(7)
C9 C5 C6 C7 -1.7(7)
C2 C1 C6 C5 1.7(9)
Br1 C1 C6 C5 179.7(4)
C2 C1 C6 C7 -178.4(6)
Br1 C1 C6 C7 -0.4(9)
C5 C6 C7 C8 -3.6(7)
C1 C6 C7 C8 176.4(6)
C6 C7 C8 O1 129.9(5)
C6 C7 C8 C10 -105.7(5)
C6 C7 C8 C9 7.1(6)
C6 C5 C9 O2 -172.8(6)
C4 C5 C9 O2 5.5(11)
C6 C5 C9 C8 6.4(6)
C4 C5 C9 C8 -175.4(7)
O1 C8 C9 O2 45.9(8)
C10 C8 C9 O2 -71.8(7)
C7 C8 C9 O2 170.9(6)
O1 C8 C9 C5 -133.3(5)
C10 C8 C9 C5 109.0(5)
C7 C8 C9 C5 -8.3(6)
C11 N1 C10 O3 3.9(11)
C11 N1 C10 C8 -175.0(6)
O1 C8 C10 O3 172.9(6)
C9 C8 C10 O3 -67.4(7)
C7 C8 C10 O3 45.0(8)
O1 C8 C10 N1 -8.1(7)
C9 C8 C10 N1 111.5(6)
C7 C8 C10 N1 -136.0(6)
C10 N1 C11 C16 -18.7(12)
C10 N1 C11 C12 162.2(7)
C16 C11 C12 C13 1.0(13)
N1 C11 C12 C13 -179.8(7)
C11 C12 C13 C14 -0.9(14)
C12 C13 C14 C15 0.7(18)
C13 C14 C15 C16 0(2)
C12 C11 C16 C15 -0.8(16)
N1 C11 C16 C15 -180.0(10)
C14 C15 C16 C11 1(2)
