 
data_2010src0792ra
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety
 'C15 H10 Br N O, H2 O'
_chemical_formula_sum
 'C15 H12 Br N O2'
_chemical_formula_weight          318.17
 
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'
 
_symmetry_cell_setting            monoclinic
_symmetry_space_group_name_H-M    'C 2/c'
_symmetry_space_group_name_Hall   '-C 2yc'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y, -z+1/2'
 'x+1/2, y+1/2, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y, z-1/2'
 '-x+1/2, -y+1/2, -z'
 'x+1/2, -y+1/2, z-1/2'
 
_cell_length_a                    19.623(3)
_cell_length_b                    4.0710(5)
_cell_length_c                    32.979(4)
_cell_angle_alpha                 90.00
_cell_angle_beta                  101.698(3)
_cell_angle_gamma                 90.00
_cell_volume                      2579.8(6)
_cell_formula_units_Z             8
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     25615
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             yellow
_exptl_crystal_size_max           0.10
_exptl_crystal_size_mid           0.04
_exptl_crystal_size_min           0.02
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.638
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1280
_exptl_absorpt_coefficient_mu     3.183
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.7414
_exptl_absorpt_correction_T_max   0.9391
_exptl_absorpt_process_details    'SADABS 2007/2 (Sheldrick, G.M., 2007)'

 
_exptl_special_details
;
SADABS was used to perform the Absorption correction
Parameter refinement on 7365 reflections reduced R(int) from 0.1306 to 0.0675
Ratio of minimum to maximum apparent transmission:  0.767895
The given Tmin and Tmax were generated using the SHELX SIZE command

The H-atoms associated with the solvent water molecule could not be reliably
located in the difference map but are included in the sum and moiety formulae
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Bruker Nonius FR591 Rotating Anode'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_measurement_device_type 
  'Bruker-Nonius APEX II CCD camera on κ-goniostat'
_diffrn_measurement_method        'φ & ω scans to fill the asymmetric unit'
_diffrn_detector_area_resol_mean  66.065
_diffrn_standards_number          0
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             9093
_diffrn_reflns_av_R_equivalents   0.0715
_diffrn_reflns_av_sigmaI/netI     0.0842
_diffrn_reflns_limit_h_min        -24
_diffrn_reflns_limit_h_max        24
_diffrn_reflns_limit_k_min        -4
_diffrn_reflns_limit_k_max        5
_diffrn_reflns_limit_l_min        -42
_diffrn_reflns_limit_l_max        41
_diffrn_reflns_theta_min          2.95
_diffrn_reflns_theta_max          27.48
_reflns_number_total              2888
_reflns_number_gt                 2064
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        
'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'   
_computing_structure_solution   'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 
'OLEX2 (Dolomanov, Bourhis, Gildea, Howard & Puschmann, 2009)'
_computing_publication_material   'WINGX (Farrugia, 1998)' 
 
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
 
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
 'calc w=1/[σ²(Fo²)+(0.0000P)²+56.6839P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          2888
_refine_ls_number_parameters      172
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1204
_refine_ls_R_factor_gt            0.0792
_refine_ls_wR_factor_ref          0.1688
_refine_ls_wR_factor_gt           0.1462
_refine_ls_goodness_of_fit_ref    1.124
_refine_ls_restrained_S_all       1.124
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
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
 _atom_site_disorder_assembly
 _atom_site_disorder_group
C1 C 0.2771(4) -0.5058(18) 0.45224(19) 0.0247(16) Uani 1 1 d . . .
C2 C 0.2785(4) -0.3241(19) 0.41293(19) 0.0236(14) Uani 1 1 d . . .
C3 C 0.2090(3) -0.1948(18) 0.39907(19) 0.0227(14) Uani 1 1 d . . .
C4 C 0.1755(4) 0.0037(17) 0.3660(2) 0.0245(16) Uani 1 1 d . . .
H4 H 0.2002 0.0756 0.3456 0.029 Uiso 1 1 calc R . .
C5 C 0.1064(4) 0.0944(18) 0.3631(2) 0.0277(16) Uani 1 1 d . . .
H5 H 0.0843 0.2284 0.3407 0.033 Uiso 1 1 calc R . .
C6 C 0.0691(4) -0.0080(19) 0.3925(2) 0.0288(17) Uani 1 1 d . . .
H6 H 0.0215 0.0506 0.3895 0.035 Uiso 1 1 calc R . .
C7 C 0.1013(4) -0.196(2) 0.4263(2) 0.0282(16) Uani 1 1 d . . .
H7 H 0.0769 -0.2588 0.4472 0.034 Uiso 1 1 calc R . .
C8 C 0.1699(3) -0.2880(17) 0.42859(18) 0.0214(14) Uani 1 1 d . . .
C9 C 0.3394(4) -0.3067(18) 0.3994(2) 0.0253(15) Uani 1 1 d . . .
H9 H 0.3796 -0.3886 0.4177 0.030 Uiso 1 1 calc R . .
C10 C 0.3502(4) -0.1743(19) 0.35931(19) 0.0246(15) Uani 1 1 d . . .
C11 C 0.3037(4) -0.2445(17) 0.3227(2) 0.0255(16) Uani 1 1 d . . .
H11 H 0.2626 -0.3656 0.3235 0.031 Uiso 1 1 calc R . .
C12 C 0.3166(4) -0.1394(17) 0.28476(19) 0.0244(15) Uani 1 1 d . . .
H12 H 0.2849 -0.1875 0.2597 0.029 Uiso 1 1 calc R . .
C13 C 0.3770(4) 0.0373(18) 0.2846(2) 0.0250(16) Uani 1 1 d . . .
C14 C 0.4253(4) 0.1065(18) 0.3205(2) 0.0269(16) Uani 1 1 d . . .
H14 H 0.4666 0.2252 0.3196 0.032 Uiso 1 1 calc R . .
C15 C 0.4113(4) -0.0033(19) 0.3581(2) 0.0283(17) Uani 1 1 d . . .
H15 H 0.4438 0.0389 0.3831 0.034 Uiso 1 1 calc R . .
N1 N 0.2114(3) -0.4743(15) 0.45970(16) 0.0249(13) Uani 1 1 d . . .
H1 H 0.1972 -0.5594 0.4811 0.030 Uiso 1 1 calc R . .
O1 O 0.3249(3) -0.6564(14) 0.47460(13) 0.0303(12) Uani 1 1 d . . .
Br1 Br 0.39394(4) 0.1889(2) 0.23279(2) 0.0310(2) Uani 1 1 d . . .
O1W1 O 0.4676(4) -0.746(3) 0.4773(2) 0.103(4) Uani 1 1 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
C1 0.029(4) 0.026(4) 0.018(3) -0.006(3) 0.005(3) -0.005(3)
C2 0.025(4) 0.027(4) 0.021(3) -0.005(3) 0.007(3) -0.002(3)
C3 0.023(3) 0.024(4) 0.022(3) -0.013(3) 0.005(3) -0.008(3)
C4 0.036(4) 0.018(4) 0.022(3) -0.006(3) 0.011(3) -0.003(3)
C5 0.032(4) 0.024(4) 0.027(3) -0.002(3) 0.008(3) 0.003(3)
C6 0.026(4) 0.032(4) 0.029(4) -0.005(3) 0.006(3) -0.001(3)
C7 0.029(4) 0.034(4) 0.023(3) -0.002(3) 0.007(3) 0.003(4)
C8 0.022(3) 0.022(4) 0.019(3) -0.005(3) 0.001(2) -0.003(3)
C9 0.031(4) 0.018(3) 0.028(3) -0.003(3) 0.010(3) 0.006(3)
C10 0.027(4) 0.025(4) 0.022(3) 0.000(3) 0.006(3) 0.009(3)
C11 0.023(4) 0.024(4) 0.031(3) 0.002(3) 0.011(3) 0.003(3)
C12 0.029(4) 0.023(4) 0.021(3) 0.001(3) 0.004(3) -0.003(3)
C13 0.031(4) 0.026(4) 0.023(3) 0.002(3) 0.016(3) 0.001(3)
C14 0.029(4) 0.022(4) 0.034(4) -0.001(3) 0.016(3) 0.000(3)
C15 0.023(4) 0.033(5) 0.031(4) -0.002(3) 0.008(3) 0.007(3)
N1 0.019(3) 0.038(4) 0.019(3) -0.004(3) 0.006(2) 0.001(3)
O1 0.026(3) 0.043(3) 0.021(2) 0.002(2) 0.002(2) -0.001(3)
Br1 0.0366(4) 0.0318(4) 0.0275(3) 0.0053(3) 0.0135(3) 0.0005(4)
O1W1 0.034(4) 0.213(11) 0.067(5) 0.039(6) 0.018(4) 0.017(6)
 
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
C1 O1 1.232(8) . ?
C1 N1 1.368(9) . ?
C1 C2 1.498(9) . ?
C2 C9 1.361(9) . ?
C2 C3 1.447(10) . ?
C3 C8 1.408(9) . ?
C3 C4 1.409(10) . ?
C4 C5 1.389(10) . ?
C4 H4 0.9500 . ?
C5 C6 1.394(9) . ?
C5 H5 0.9500 . ?
C6 C7 1.393(10) . ?
C6 H6 0.9500 . ?
C7 C8 1.386(9) . ?
C7 H7 0.9500 . ?
C8 N1 1.397(9) . ?
C9 C10 1.482(9) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(9) . ?
C10 C15 1.394(10) . ?
C11 C12 1.393(9) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(10) . ?
C12 H12 0.9500 . ?
C13 C14 1.388(10) . ?
C13 Br1 1.906(6) . ?
C14 C15 1.394(9) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
N1 H1 0.8800 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
O1 C1 N1 124.7(6) . . ?
O1 C1 C2 128.2(6) . . ?
N1 C1 C2 107.0(6) . . ?
C9 C2 C3 135.4(7) . . ?
C9 C2 C1 118.7(7) . . ?
C3 C2 C1 105.8(5) . . ?
C8 C3 C4 117.1(6) . . ?
C8 C3 C2 107.1(6) . . ?
C4 C3 C2 135.7(6) . . ?
C5 C4 C3 120.1(6) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 121.1(7) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C7 C6 C5 120.3(7) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C8 C7 C6 118.0(6) . . ?
C8 C7 H7 121.0 . . ?
C6 C7 H7 121.0 . . ?
C7 C8 N1 127.0(6) . . ?
C7 C8 C3 123.3(6) . . ?
N1 C8 C3 109.7(6) . . ?
C2 C9 C10 127.2(7) . . ?
C2 C9 H9 116.4 . . ?
C10 C9 H9 116.4 . . ?
C11 C10 C15 119.6(6) . . ?
C11 C10 C9 121.0(7) . . ?
C15 C10 C9 119.2(6) . . ?
C10 C11 C12 120.8(7) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C13 C12 C11 118.3(6) . . ?
C13 C12 H12 120.8 . . ?
C11 C12 H12 120.8 . . ?
C12 C13 C14 122.4(6) . . ?
C12 C13 Br1 118.4(5) . . ?
C14 C13 Br1 119.2(5) . . ?
C13 C14 C15 118.1(7) . . ?
C13 C14 H14 121.0 . . ?
C15 C14 H14 121.0 . . ?
C14 C15 C10 120.8(7) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
C1 N1 C8 110.4(5) . . ?
C1 N1 H1 124.8 . . ?
C8 N1 H1 124.8 . . ?
 
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 H1 O1  0.88 1.98 2.843(7) 166.8 7_536
 
_diffrn_measured_fraction_theta_max    0.976
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.976
_refine_diff_density_max    0.649
_refine_diff_density_min   -0.825
_refine_diff_density_rms    0.163
