 
data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C19 H33 Br N2 O'
_chemical_formula_weight          385.38
 
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'
 'Br'  'Br'  -0.2901   2.4595
 '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'
 
_symmetry_cell_setting            Triclinic
_symmetry_space_group_name_H-M    P-1
_symmetry_space_group_name_hall   '-P 1'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    8.8931(3)
_cell_length_b                    9.0266(2)
_cell_length_c                    13.6881(6)
_cell_angle_alpha                 72.225(2)
_cell_angle_beta                  77.2341(18)
_cell_angle_gamma                 77.122(2)
_cell_volume                      1006.10(6)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     17263
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        plate
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.24
_exptl_crystal_size_mid           0.20
_exptl_crystal_size_min           0.01
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.272
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              408
_exptl_absorpt_coefficient_mu     2.050
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.6390
_exptl_absorpt_correction_T_max   0.9898
_exptl_absorpt_process_details    'SORTAV (Blessing, 1997)'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\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             20583
_diffrn_reflns_av_R_equivalents   0.0727
_diffrn_reflns_av_sigmaI/netI     0.0500
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        11
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -17
_diffrn_reflns_limit_l_max        17
_diffrn_reflns_theta_min          2.96
_diffrn_reflns_theta_max          27.50
_reflns_number_total              4615
_reflns_number_gt                 3747
_reflns_threshold_expression      >2σ(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 > 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)+(0.0405P)²+0.7977P] 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        0.0062(13)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          4615
_refine_ls_number_parameters      217
_refine_ls_number_restraints      3
_refine_ls_R_factor_all           0.0563
_refine_ls_R_factor_gt            0.0397
_refine_ls_wR_factor_ref          0.0950
_refine_ls_wR_factor_gt           0.0879
_refine_ls_goodness_of_fit_ref    0.975
_refine_ls_restrained_S_all       0.977
_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
Br1 Br 0.16555(3) 0.12565(3) 0.57768(2) 0.03797(11) Uani 1 1 d . . .
N1 N 0.3896(2) 0.7603(2) 0.36326(15) 0.0238(4) Uani 1 1 d . . .
N2 N 0.2491(2) 0.5930(2) 0.35934(16) 0.0250(4) Uani 1 1 d . . .
C1 C 0.4172(4) 1.3564(4) -0.0978(2) 0.0534(8) Uani 1 1 d . . .
H1A H 0.4468 1.4422 -0.0802 0.080 Uiso 1 1 calc R . .
H1B H 0.3403 1.4004 -0.1450 0.080 Uiso 1 1 calc R . .
H1C H 0.5102 1.2985 -0.1319 0.080 Uiso 1 1 calc R . .
C2 C 0.3467(3) 1.2450(3) 0.0006(2) 0.0396(6) Uani 1 1 d . . .
H2A H 0.2517 1.3038 0.0339 0.048 Uiso 1 1 calc R . .
H2B H 0.3146 1.1603 -0.0180 0.048 Uiso 1 1 calc R . .
C3 C 0.4583(3) 1.1715(3) 0.0775(2) 0.0354(6) Uani 1 1 d . . .
H3A H 0.4938 1.2568 0.0933 0.042 Uiso 1 1 calc R . .
H3B H 0.5514 1.1098 0.0446 0.042 Uiso 1 1 calc R . .
C4 C 0.3901(3) 1.0645(3) 0.1785(2) 0.0332(6) Uani 1 1 d . . .
H4A H 0.3565 0.9776 0.1633 0.040 Uiso 1 1 calc R . .
H4B H 0.2963 1.1253 0.2114 0.040 Uiso 1 1 calc R . .
C5 C 0.5054(3) 0.9947(3) 0.2546(2) 0.0294(5) Uani 1 1 d . . .
H5A H 0.5911 0.9210 0.2258 0.035 Uiso 1 1 calc R . .
H5B H 0.5519 1.0810 0.2604 0.035 Uiso 1 1 calc R . .
C6 C 0.4353(3) 0.9076(3) 0.3624(2) 0.0293(5) Uani 1 1 d . . .
H6A H 0.5125 0.8829 0.4097 0.035 Uiso 1 1 calc R . .
H6B H 0.3423 0.9767 0.3889 0.035 Uiso 1 1 calc R . .
C7 C 0.2485(3) 0.7405(3) 0.35921(19) 0.0260(5) Uani 1 1 d . . .
H7 H 0.1587 0.8208 0.3566 0.031 Uiso 1 1 calc R . .
C8 C 0.4903(3) 0.6176(2) 0.36627(18) 0.0235(5) Uani 1 1 d . . .
C9 C 0.6486(3) 0.5730(3) 0.37308(19) 0.0271(5) Uani 1 1 d . . .
H9 H 0.7098 0.6455 0.3752 0.033 Uiso 1 1 calc R . .
C10 C 0.7113(3) 0.4184(3) 0.37657(19) 0.0292(5) Uani 1 1 d . . .
H10 H 0.8192 0.3831 0.3807 0.035 Uiso 1 1 calc R . .
C11 C 0.6206(3) 0.3108(3) 0.37420(19) 0.0297(5) Uani 1 1 d . . .
H11 H 0.6688 0.2048 0.3771 0.036 Uiso 1 1 calc R . .
C12 C 0.4642(3) 0.3548(3) 0.36776(19) 0.0278(5) Uani 1 1 d . . .
H12 H 0.4028 0.2821 0.3661 0.033 Uiso 1 1 calc R . .
C13 C 0.4009(3) 0.5109(3) 0.36378(18) 0.0235(5) Uani 1 1 d . . .
C14 C 0.1175(3) 0.5283(3) 0.3497(2) 0.0302(5) Uani 1 1 d . . .
H14A H 0.0183 0.5968 0.3686 0.036 Uiso 1 1 calc R . .
H14B H 0.1163 0.4222 0.3990 0.036 Uiso 1 1 calc R . .
C15 C 0.1281(3) 0.5165(3) 0.2402(2) 0.0315(5) Uani 1 1 d . . .
H15A H 0.0501 0.4531 0.2408 0.038 Uiso 1 1 calc R . .
H15B H 0.2330 0.4592 0.2188 0.038 Uiso 1 1 calc R . .
C16 C 0.1009(3) 0.6738(3) 0.1597(2) 0.0333(6) Uani 1 1 d . . .
H16A H 0.1771 0.7389 0.1597 0.040 Uiso 1 1 calc R . .
H16B H -0.0053 0.7302 0.1792 0.040 Uiso 1 1 calc R . .
C17 C 0.1173(3) 0.6559(3) 0.0509(2) 0.0360(6) Uani 1 1 d . . .
H17A H 0.2237 0.5994 0.0321 0.043 Uiso 1 1 calc R . .
H17B H 0.0419 0.5895 0.0518 0.043 Uiso 1 1 calc R . .
C18 C 0.0902(3) 0.8097(3) -0.0323(2) 0.0397(6) Uani 1 1 d . . .
H18A H -0.0175 0.8650 -0.0152 0.048 Uiso 1 1 calc R . .
H18B H 0.1635 0.8778 -0.0323 0.048 Uiso 1 1 calc R . .
C19 C 0.1123(4) 0.7872(4) -0.1396(3) 0.0560(8) Uani 1 1 d . . .
H19A H 0.2181 0.7308 -0.1566 0.084 Uiso 1 1 calc R . .
H19B H 0.0977 0.8904 -0.1905 0.084 Uiso 1 1 calc R . .
H19C H 0.0354 0.7257 -0.1414 0.084 Uiso 1 1 calc R . .
O1 O 1.0556(3) 0.1519(3) 0.3619(2) 0.0595(6) Uani 1 1 d D . .
H51 H 0.988(4) 0.085(4) 0.375(3) 0.089 Uiso 1 1 d D . .
H52 H 1.078(5) 0.143(5) 0.425(2) 0.089 Uiso 1 1 d 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
N1 C7 1.322(3) . ?
N1 C8 1.390(3) . ?
N1 C6 1.471(3) . ?
N2 C7 1.329(3) . ?
N2 C13 1.392(3) . ?
N2 C14 1.466(3) . ?
C1 C2 1.517(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.508(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.512(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.522(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.512(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7 0.9500 . ?
C8 C9 1.391(3) . ?
C8 C13 1.391(3) . ?
C9 C10 1.373(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.405(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.374(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.386(3) . ?
C12 H12 0.9500 . ?
C14 C15 1.516(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.516(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.518(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.513(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.508(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
O1 H51 0.897(18) . ?
O1 H52 0.907(18) . ?
 
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
C7 N1 C8 108.19(18) . . ?
C7 N1 C6 126.61(19) . . ?
C8 N1 C6 125.18(19) . . ?
C7 N2 C13 107.88(18) . . ?
C7 N2 C14 126.91(19) . . ?
C13 N2 C14 125.10(18) . . ?
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 . . ?
C3 C2 C1 112.8(3) . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C2 C3 C4 114.4(2) . . ?
C2 C3 H3A 108.7 . . ?
C4 C3 H3A 108.7 . . ?
C2 C3 H3B 108.7 . . ?
C4 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
C3 C4 C5 112.8(2) . . ?
C3 C4 H4A 109.0 . . ?
C5 C4 H4A 109.0 . . ?
C3 C4 H4B 109.0 . . ?
C5 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C6 C5 C4 114.6(2) . . ?
C6 C5 H5A 108.6 . . ?
C4 C5 H5A 108.6 . . ?
C6 C5 H5B 108.6 . . ?
C4 C5 H5B 108.6 . . ?
H5A C5 H5B 107.6 . . ?
N1 C6 C5 112.0(2) . . ?
N1 C6 H6A 109.2 . . ?
C5 C6 H6A 109.2 . . ?
N1 C6 H6B 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
N1 C7 N2 110.85(19) . . ?
N1 C7 H7 124.6 . . ?
N2 C7 H7 124.6 . . ?
C9 C8 C13 121.7(2) . . ?
C9 C8 N1 131.8(2) . . ?
C13 C8 N1 106.54(19) . . ?
C10 C9 C8 116.2(2) . . ?
C10 C9 H9 121.9 . . ?
C8 C9 H9 121.9 . . ?
C9 C10 C11 122.0(2) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
C12 C11 C10 121.8(2) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C13 116.3(2) . . ?
C11 C12 H12 121.8 . . ?
C13 C12 H12 121.8 . . ?
C12 C13 C8 122.0(2) . . ?
C12 C13 N2 131.4(2) . . ?
C8 C13 N2 106.54(18) . . ?
N2 C14 C15 111.7(2) . . ?
N2 C14 H14A 109.3 . . ?
C15 C14 H14A 109.3 . . ?
N2 C14 H14B 109.3 . . ?
C15 C14 H14B 109.3 . . ?
H14A C14 H14B 107.9 . . ?
C14 C15 C16 114.6(2) . . ?
C14 C15 H15A 108.6 . . ?
C16 C15 H15A 108.6 . . ?
C14 C15 H15B 108.6 . . ?
C16 C15 H15B 108.6 . . ?
H15A C15 H15B 107.6 . . ?
C15 C16 C17 112.6(2) . . ?
C15 C16 H16A 109.1 . . ?
C17 C16 H16A 109.1 . . ?
C15 C16 H16B 109.1 . . ?
C17 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
C18 C17 C16 114.7(2) . . ?
C18 C17 H17A 108.6 . . ?
C16 C17 H17A 108.6 . . ?
C18 C17 H17B 108.6 . . ?
C16 C17 H17B 108.6 . . ?
H17A C17 H17B 107.6 . . ?
C19 C18 C17 113.0(2) . . ?
C19 C18 H18A 109.0 . . ?
C17 C18 H18A 109.0 . . ?
C19 C18 H18B 109.0 . . ?
C17 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
H51 O1 H52 104(3) . . ?
 
_diffrn_measured_fraction_theta_max    0.997
_diffrn_reflns_theta_full              27.50
_diffrn_measured_fraction_theta_full   0.997
_refine_diff_density_max    1.124
_refine_diff_density_min   -0.713
_refine_diff_density_rms    0.066
