data_03src0042
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C15 H25 Br N2 O'
_chemical_formula_weight          329.28
 
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)/c
_symmetry_space_group_name_hall   '-P 2ybc'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    8.76900(10)
_cell_length_b                    18.3239(6)
_cell_length_c                    10.4942(3)
_cell_angle_alpha                 90.00
_cell_angle_beta                  107.374(2)
_cell_angle_gamma                 90.00
_cell_volume                      1609.30(7)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     8966
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        rod
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.40
_exptl_crystal_size_mid           0.18
_exptl_crystal_size_min           0.12
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.359
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              688
_exptl_absorpt_coefficient_mu     2.550
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.4286
_exptl_absorpt_correction_T_max   0.7495
_exptl_absorpt_process_details    'SORTAV (Blessing, 1997)'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            'Mo K\a'
_diffrn_radiation_source          'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method        'ω and φ scans to fill Ewald sphere'
_diffrn_detector_area_resol_mean  '9.091 pixels/mm'
_diffrn_standards_number          'n/a'
_diffrn_standards_interval_count  'n/a'
_diffrn_standards_interval_time   'n/a'
_diffrn_standards_decay_%         'n/a'
_diffrn_reflns_number             19260
_diffrn_reflns_av_R_equivalents   0.0590
_diffrn_reflns_av_sigmaI/netI     0.0378
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        11
_diffrn_reflns_limit_k_min        -23
_diffrn_reflns_limit_k_max        22
_diffrn_reflns_limit_l_min        -13
_diffrn_reflns_limit_l_max        13
_diffrn_reflns_theta_min          3.01
_diffrn_reflns_theta_max          27.49
_reflns_number_total              3676
_reflns_number_gt                 2908
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        
;
'DENZO (Otwinowski and Minor, 1997) & COLLECT (Hooft, 1998) '
;
_computing_cell_refinement        'DENZO and COLLECT'
_computing_data_reduction         'DENZO and COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)' 
_computing_molecular_graphics     ?
_computing_publication_material   SHELXL-97
_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)+(0.0510P)²+0.1656P] 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      SHELXL
_refine_ls_extinction_coef        0.0047(8)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          3676
_refine_ls_number_parameters      183
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0500
_refine_ls_R_factor_gt            0.0334
_refine_ls_wR_factor_ref          0.0867
_refine_ls_wR_factor_gt           0.0797
_refine_ls_goodness_of_fit_ref    1.019
_refine_ls_restrained_S_all       1.019
_refine_ls_shift/su_max           0.012
_refine_ls_shift/su_mean          0.001
 
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 0.4576(4) 0.71900(15) 1.0780(3) 0.0494(7) Uani 1 1 d . . .
H1A H 0.5603 0.7447 1.1046 0.074 Uiso 1 1 calc R . .
H1B H 0.4190 0.7130 1.1559 0.074 Uiso 1 1 calc R . .
H1C H 0.3798 0.7474 1.0095 0.074 Uiso 1 1 calc R . .
C2 C 0.4785(3) 0.64533(12) 1.0229(2) 0.0316(5) Uani 1 1 d . . .
H2A H 0.3755 0.6188 1.0006 0.038 Uiso 1 1 calc R . .
H2B H 0.5574 0.6170 1.0927 0.038 Uiso 1 1 calc R . .
C3 C 0.5339(3) 0.64939(13) 0.9000(2) 0.0334(5) Uani 1 1 d . . .
H3A H 0.4508 0.6740 0.8276 0.040 Uiso 1 1 calc R . .
H3B H 0.6323 0.6793 0.9201 0.040 Uiso 1 1 calc R . .
C4 C 0.5670(3) 0.57518(12) 0.8524(2) 0.0261(4) Uani 1 1 d . . .
H4A H 0.6560 0.5518 0.9215 0.031 Uiso 1 1 calc R . .
H4B H 0.4712 0.5439 0.8377 0.031 Uiso 1 1 calc R . .
C5 C 0.7551(2) 0.58919(11) 0.71698(19) 0.0223(4) Uani 1 1 d . . .
H5 H 0.8503 0.5885 0.7900 0.027 Uiso 1 1 calc R . .
C6 C 0.5010(2) 0.58545(10) 0.59996(19) 0.0208(4) Uani 1 1 d . . .
C7 C 0.3368(2) 0.57958(11) 0.5557(2) 0.0249(4) Uani 1 1 d . . .
H7 H 0.2758 0.5721 0.6157 0.030 Uiso 1 1 calc R . .
C8 C 0.2657(2) 0.58520(11) 0.4195(2) 0.0273(5) Uani 1 1 d . . .
H8 H 0.1528 0.5816 0.3845 0.033 Uiso 1 1 calc R . .
C9 C 0.3570(2) 0.59614(12) 0.3321(2) 0.0285(5) Uani 1 1 d . . .
H9 H 0.3037 0.6002 0.2392 0.034 Uiso 1 1 calc R . .
C10 C 0.5210(2) 0.60120(12) 0.37574(19) 0.0262(4) Uani 1 1 d . . .
H10 H 0.5826 0.6079 0.3160 0.031 Uiso 1 1 calc R . .
C11 C 0.5908(2) 0.59588(11) 0.51316(19) 0.0207(4) Uani 1 1 d . . .
C12 C 0.8876(2) 0.61012(12) 0.5415(2) 0.0290(5) Uani 1 1 d . . .
H12A H 0.8751 0.5808 0.4598 0.035 Uiso 1 1 calc R . .
H12B H 0.9862 0.5938 0.6098 0.035 Uiso 1 1 calc R . .
C13 C 0.9030(3) 0.69021(15) 0.5104(3) 0.0460(7) Uani 1 1 d . . .
H13A H 0.8020 0.7066 0.4454 0.055 Uiso 1 1 calc R . .
H13B H 0.9891 0.6957 0.4679 0.055 Uiso 1 1 calc R . .
C14 C 0.9399(4) 0.73930(15) 0.6331(4) 0.0622(9) Uani 1 1 d . . .
H14A H 0.9368 0.7908 0.6038 0.075 Uiso 1 1 calc R . .
H14B H 0.8551 0.7328 0.6767 0.075 Uiso 1 1 calc R . .
C15 C 1.0994(4) 0.7249(2) 0.7344(4) 0.0741(10) Uani 1 1 d . . .
H15A H 1.0980 0.6766 0.7744 0.111 Uiso 1 1 calc R . .
H15B H 1.1205 0.7623 0.8042 0.111 Uiso 1 1 calc R . .
H15C H 1.1835 0.7263 0.6904 0.111 Uiso 1 1 calc R . .
N1 N 0.60910(19) 0.58143(9) 0.72769(16) 0.0216(3) Uani 1 1 d . . .
N2 N 0.75020(19) 0.59801(9) 0.59067(16) 0.0219(3) Uani 1 1 d . . .
Br1 Br 0.14769(2) 0.480936(13) 0.80196(2) 0.03247(11) Uani 1 1 d . . .
O1 O 1.0399(2) 0.59946(11) 0.9975(2) 0.0468(4) Uani 1 1 d . . .
H1O H 0.995(4) 0.5780(19) 1.050(4) 0.066(11) Uiso 1 1 d . . .
H2O H 1.087(5) 0.562(3) 0.965(4) 0.108(15) Uiso 1 1 d . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds 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 C2 1.501(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.510(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.507(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 N1 1.466(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N2 1.323(3) . ?
C5 N1 1.326(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.379(3) . ?
C6 C11 1.384(3) . ?
C6 N1 1.394(2) . ?
C7 C8 1.382(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.400(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.376(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.392(3) . ?
C10 H10 0.9500 . ?
C11 N2 1.392(2) . ?
C12 N2 1.463(2) . ?
C12 C13 1.518(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.524(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.506(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
O1 H1O 0.86(4) . ?
O1 H2O 0.93(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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C1 C2 C3 113.07(19) . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
C3 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C4 C3 C2 112.46(18) . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
N1 C4 C3 110.52(17) . . ?
N1 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
N2 C5 N1 110.77(16) . . ?
N2 C5 H5 124.6 . . ?
N1 C5 H5 124.6 . . ?
C7 C6 C11 122.10(18) . . ?
C7 C6 N1 131.45(19) . . ?
C11 C6 N1 106.44(17) . . ?
C6 C7 C8 116.47(19) . . ?
C6 C7 H7 121.8 . . ?
C8 C7 H7 121.8 . . ?
C7 C8 C9 121.2(2) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C10 C9 C8 122.45(19) . . ?
C10 C9 H9 118.8 . . ?
C8 C9 H9 118.8 . . ?
C9 C10 C11 115.65(19) . . ?
C9 C10 H10 122.2 . . ?
C11 C10 H10 122.2 . . ?
C6 C11 C10 122.08(18) . . ?
C6 C11 N2 106.79(17) . . ?
C10 C11 N2 131.13(18) . . ?
N2 C12 C13 110.99(18) . . ?
N2 C12 H12A 109.4 . . ?
C13 C12 H12A 109.4 . . ?
N2 C12 H12B 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C12 C13 C14 113.5(2) . . ?
C12 C13 H13A 108.9 . . ?
C14 C13 H13A 108.9 . . ?
C12 C13 H13B 108.9 . . ?
C14 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C15 C14 C13 114.3(2) . . ?
C15 C14 H14A 108.7 . . ?
C13 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
C13 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C5 N1 C6 108.04(16) . . ?
C5 N1 C4 126.21(16) . . ?
C6 N1 C4 125.61(16) . . ?
C5 N2 C11 107.97(16) . . ?
C5 N2 C12 126.02(16) . . ?
C11 N2 C12 125.99(17) . . ?
H1O O1 H2O 104(4) . . ?
 
_diffrn_measured_fraction_theta_max    0.994
_diffrn_reflns_theta_full              27.49
_diffrn_measured_fraction_theta_full   0.994
_refine_diff_density_max    0.507
_refine_diff_density_min   -0.721
_refine_diff_density_rms    0.070
