 
data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C12 H19 Br N2 O'
_chemical_formula_weight          287.20
 
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'
 'Br'  'Br'  -0.2901   2.4595
 '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'
 
_symmetry_cell_setting            Monoclinic
_symmetry_space_group_name_H-M    P2(1)/n
_symmetry_space_group_name_hall   '-P 2yn'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'
 
_cell_length_a                    5.1010(2)
_cell_length_b                    18.7081(8)
_cell_length_c                    13.7459(7)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.676(2)
_cell_angle_gamma                 90.00
_cell_volume                      1311.68(10)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     25197
_cell_measurement_theta_min       5.11
_cell_measurement_theta_max       23.24
 
_exptl_crystal_description        Block
_exptl_crystal_colour             Colourless
_exptl_crystal_size_max           0.20
_exptl_crystal_size_mid           0.20
_exptl_crystal_size_min           0.20
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.454
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              592
_exptl_absorpt_coefficient_mu     3.117
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.5745
_exptl_absorpt_correction_T_max   0.5745
_exptl_absorpt_process_details    'SORTAV Blessing (1997)'
 
_exptl_special_details
;
 PLEASE NOTE cell_measurement_ fields are not relevant to area detector data,
 the entire data set is used to refine the cell, which is indexed from all
 observed reflections in a 10 degree phi range.
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Nonius KappaCCD Area Detector'
_diffrn_measurement_method        'φ and ω scans to fill Ewald Sphere'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             7915
_diffrn_reflns_av_R_equivalents   0.0697
_diffrn_reflns_av_sigmaI/netI     0.0549
_diffrn_reflns_limit_h_min        -5
_diffrn_reflns_limit_h_max        6
_diffrn_reflns_limit_k_min        -22
_diffrn_reflns_limit_k_max        21
_diffrn_reflns_limit_l_min        -16
_diffrn_reflns_limit_l_max        16
_diffrn_reflns_theta_min          2.96
_diffrn_reflns_theta_max          25.02
_reflns_number_total              2291
_reflns_number_gt                 1857
_reflns_threshold_expression      >2sigma(I)
 
__computing_data_collection
' DENZO (Otwinowski and Minor, 1997)'
_computing_cell_refinement        
' DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_reduction         
' DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997a)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997b)' 
_computing_molecular_graphics     'PLATON (Spek, 1990)'
_computing_publication_material   ? 
 
_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 > 2sigma(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)+(0.0529P)²+0.3265P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          2291
_refine_ls_number_parameters      221
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0527
_refine_ls_R_factor_gt            0.0387
_refine_ls_wR_factor_ref          0.0998
_refine_ls_wR_factor_gt           0.0920
_refine_ls_goodness_of_fit_ref    1.060
_refine_ls_restrained_S_all       1.060
_refine_ls_shift/su_max           0.001
_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
Br1 Br 0.21947(6) 0.835350(18) 0.47069(2) 0.02970(17) Uani 1 1 d . . .
C7 C -0.7476(7) 0.66330(16) 0.1443(2) 0.0235(7) Uani 1 1 d . . .
N1 N -0.6414(5) 0.59956(14) 0.16307(19) 0.0232(6) Uani 1 1 d . . .
N2 N -0.6308(5) 0.71334(13) 0.19675(19) 0.0219(6) Uani 1 1 d . . .
C4 C -0.0776(7) 0.66251(17) 0.3597(3) 0.0258(8) Uani 1 1 d . . .
C5 C -0.2549(6) 0.70988(18) 0.3188(2) 0.0231(7) Uani 1 1 d . . .
C3 C -0.0841(7) 0.58935(18) 0.3364(2) 0.0261(7) Uani 1 1 d . . .
C2 C -0.2631(6) 0.56116(19) 0.2718(2) 0.0250(7) Uani 1 1 d . . .
C9 C -0.6909(7) 0.79033(17) 0.1984(3) 0.0252(8) Uani 1 1 d . . .
C12 C -1.1342(8) 0.9129(2) 0.0424(3) 0.0326(8) Uani 1 1 d . . .
C1 C -0.4406(6) 0.60881(16) 0.2300(2) 0.0224(7) Uani 1 1 d . . .
C8 C -0.7145(8) 0.53227(19) 0.1151(3) 0.0304(8) Uani 1 1 d . . .
C6 C -0.4336(6) 0.68164(17) 0.2528(2) 0.0218(7) Uani 1 1 d . . .
C10 C -0.8793(7) 0.81132(19) 0.1180(3) 0.0263(8) Uani 1 1 d . . .
C11 C -0.9361(7) 0.89163(18) 0.1198(3) 0.0281(8) Uani 1 1 d . . .
O1W O 0.7165(6) 0.90407(15) 0.3459(2) 0.0400(7) Uani 1 1 d . . .
H9A H -0.751(6) 0.8025(18) 0.263(3) 0.022(8) Uiso 1 1 d . . .
H7 H -0.884(6) 0.6687(14) 0.098(2) 0.014(8) Uiso 1 1 d . . .
H12A H -1.067(6) 0.9020(17) -0.023(3) 0.022(9) Uiso 1 1 d . . .
H11B H -1.003(6) 0.8998(17) 0.181(3) 0.022(9) Uiso 1 1 d . . .
H3 H 0.045(7) 0.5599(18) 0.367(2) 0.028(9) Uiso 1 1 d . . .
H10A H -0.814(7) 0.7991(18) 0.051(3) 0.028(9) Uiso 1 1 d . . .
H12C H -1.299(7) 0.8873(17) 0.050(2) 0.019(8) Uiso 1 1 d . . .
H5 H -0.250(7) 0.758(2) 0.339(2) 0.030(9) Uiso 1 1 d . . .
H4 H 0.047(8) 0.6791(18) 0.401(3) 0.028(10) Uiso 1 1 d . . .
H10B H -1.044(7) 0.7848(18) 0.122(2) 0.025(9) Uiso 1 1 d . . .
H9B H -0.526(8) 0.817(2) 0.194(3) 0.041(11) Uiso 1 1 d . . .
H11A H -0.773(8) 0.916(2) 0.111(3) 0.040(10) Uiso 1 1 d . . .
H8A H -0.844(10) 0.541(2) 0.070(3) 0.060(13) Uiso 1 1 d . . .
H2 H -0.266(7) 0.5164(18) 0.253(2) 0.023(9) Uiso 1 1 d . . .
H8B H -0.770(7) 0.497(2) 0.163(3) 0.041(11) Uiso 1 1 d . . .
H12B H -1.169(7) 0.963(2) 0.045(3) 0.037(10) Uiso 1 1 d . . .
H8C H -0.574(9) 0.513(2) 0.085(3) 0.044(12) Uiso 1 1 d . . .
H1WA H 0.600(9) 0.889(2) 0.368(3) 0.038(14) Uiso 1 1 d . . .
H1WB H 0.846(10) 0.892(3) 0.382(4) 0.062(15) Uiso 1 1 d . . .
 
 
_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
C7 N2 1.320(4) . ?
C7 N1 1.334(4) . ?
C7 H7 0.94(3) . ?
N1 C1 1.380(4) . ?
N1 C8 1.467(4) . ?
N2 C6 1.392(4) . ?
N2 C9 1.473(4) . ?
C4 C5 1.381(5) . ?
C4 C3 1.406(5) . ?
C4 H4 0.90(4) . ?
C5 C6 1.383(5) . ?
C5 H5 0.94(4) . ?
C3 C2 1.372(5) . ?
C3 H3 0.95(4) . ?
C2 C1 1.390(5) . ?
C2 H2 0.87(3) . ?
C9 C10 1.507(5) . ?
C9 H9A 0.97(3) . ?
C9 H9B 0.97(4) . ?
C12 C11 1.511(5) . ?
C12 H12A 0.99(3) . ?
C12 H12C 0.98(3) . ?
C12 H12B 0.95(4) . ?
C1 C6 1.398(4) . ?
C8 H8A 0.92(5) . ?
C8 H8B 0.98(4) . ?
C8 H8C 0.91(4) . ?
C10 C11 1.530(5) . ?
C10 H10A 1.01(4) . ?
C10 H10B 0.98(3) . ?
C11 H11B 0.93(3) . ?
C11 H11A 0.96(4) . ?
O1W H1WA 0.73(4) . ?
O1W H1WB 0.85(5) . ?
 
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
N2 C7 N1 110.4(3) . . ?
N2 C7 H7 128.1(17) . . ?
N1 C7 H7 121.4(17) . . ?
C7 N1 C1 108.3(3) . . ?
C7 N1 C8 125.4(3) . . ?
C1 N1 C8 126.1(3) . . ?
C7 N2 C6 108.6(3) . . ?
C7 N2 C9 127.5(3) . . ?
C6 N2 C9 123.9(3) . . ?
C5 C4 C3 121.2(3) . . ?
C5 C4 H4 119(2) . . ?
C3 C4 H4 119(2) . . ?
C4 C5 C6 116.4(3) . . ?
C4 C5 H5 119(2) . . ?
C6 C5 H5 125(2) . . ?
C2 C3 C4 122.4(3) . . ?
C2 C3 H3 121(2) . . ?
C4 C3 H3 117(2) . . ?
C3 C2 C1 116.5(3) . . ?
C3 C2 H2 124(2) . . ?
C1 C2 H2 119(2) . . ?
N2 C9 C10 112.0(3) . . ?
N2 C9 H9A 108(2) . . ?
C10 C9 H9A 113.8(19) . . ?
N2 C9 H9B 108(2) . . ?
C10 C9 H9B 111(2) . . ?
H9A C9 H9B 103(3) . . ?
C11 C12 H12A 110.4(19) . . ?
C11 C12 H12C 111.2(19) . . ?
H12A C12 H12C 108(3) . . ?
C11 C12 H12B 111(2) . . ?
H12A C12 H12B 108(3) . . ?
H12C C12 H12B 108(3) . . ?
N1 C1 C2 132.1(3) . . ?
N1 C1 C6 106.7(3) . . ?
C2 C1 C6 121.2(3) . . ?
N1 C8 H8A 110(3) . . ?
N1 C8 H8B 110(2) . . ?
H8A C8 H8B 111(4) . . ?
N1 C8 H8C 110(2) . . ?
H8A C8 H8C 109(4) . . ?
H8B C8 H8C 106(3) . . ?
C5 C6 N2 131.8(3) . . ?
C5 C6 C1 122.3(3) . . ?
N2 C6 C1 106.0(3) . . ?
C9 C10 C11 111.3(3) . . ?
C9 C10 H10A 113.4(19) . . ?
C11 C10 H10A 107(2) . . ?
C9 C10 H10B 111.6(19) . . ?
C11 C10 H10B 109.5(19) . . ?
H10A C10 H10B 103(3) . . ?
C12 C11 C10 111.9(3) . . ?
C12 C11 H11B 110(2) . . ?
C10 C11 H11B 104(2) . . ?
C12 C11 H11A 111(2) . . ?
C10 C11 H11A 108(2) . . ?
H11B C11 H11A 111(3) . . ?
H1WA O1W H1WB 106(5) . . ?
 
_diffrn_measured_fraction_theta_max    0.990
_diffrn_reflns_theta_full              25.02
_diffrn_measured_fraction_theta_full   0.990
_refine_diff_density_max    0.632
_refine_diff_density_min   -0.796
_refine_diff_density_rms    0.095
