 
data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 Mimi Hii
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C19 H26 Br N'
_chemical_formula_weight          348.32
 
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'
 
_symmetry_cell_setting            Monoclinic
_symmetry_space_group_name_H-M    P2(1)
_symmetry_space_group_name_hall   'P 2yb'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y+1/2, -z'
 
_cell_length_a                    5.1549(2)
_cell_length_b                    31.1802(12)
_cell_length_c                    5.4853(3)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.609(2)
_cell_angle_gamma                 90.00
_cell_volume                      881.61(7)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     7683
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        Block
_exptl_crystal_colour             Colourless
_exptl_crystal_size_max           0.15
_exptl_crystal_size_mid           0.10
_exptl_crystal_size_min           0.05
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.312
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              364
_exptl_absorpt_coefficient_mu     2.326
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.7217
_exptl_absorpt_correction_T_max   0.8926
_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             3342
_diffrn_reflns_av_R_equivalents   0.0390
_diffrn_reflns_av_sigmaI/netI     0.0566
_diffrn_reflns_limit_h_min        -6
_diffrn_reflns_limit_h_max        5
_diffrn_reflns_limit_k_min        -26
_diffrn_reflns_limit_k_max        37
_diffrn_reflns_limit_l_min        -6
_diffrn_reflns_limit_l_max        6
_diffrn_reflns_theta_min          3.71
_diffrn_reflns_theta_max          25.02
_reflns_number_total              2043
_reflns_number_gt                 1936
_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)+(0.0306P)²+1.2939P] 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_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    0.006(16)
_refine_ls_number_reflns          2043
_refine_ls_number_parameters      190
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0425
_refine_ls_R_factor_gt            0.0389
_refine_ls_wR_factor_ref          0.0900
_refine_ls_wR_factor_gt           0.0883
_refine_ls_goodness_of_fit_ref    1.063
_refine_ls_restrained_S_all       1.063
_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 0.02053(9) 0.72156(3) 0.22798(7) 0.02700(19) Uani 1 1 d . . .
N1 N -0.3289(8) 0.7291(2) 0.7214(6) 0.0158(13) Uani 1 1 d . . .
H1A H -0.2156 0.7294 0.8521 0.019 Uiso 1 1 calc R . .
H1B H -0.2319 0.7290 0.5815 0.019 Uiso 1 1 calc R . .
C8 C -0.4854(12) 0.6888(3) 0.7298(12) 0.023(2) Uani 1 1 d . . .
H8A H -0.5945 0.6892 0.8773 0.028 Uiso 1 1 calc R . .
H8B H -0.6025 0.6879 0.5857 0.028 Uiso 1 1 calc R . .
C7 C -0.4882(13) 0.7687(3) 0.7266(12) 0.025(2) Uani 1 1 d . . .
H7A H -0.5736 0.7712 0.8868 0.030 Uiso 1 1 calc R . .
H7B H -0.6252 0.7670 0.5992 0.030 Uiso 1 1 calc R . .
C16 C -1.5082(11) 0.4715(2) 1.2915(9) 0.0214(14) Uani 1 1 d . . .
H16 H -1.6321 0.4678 1.4168 0.026 Uiso 1 1 calc R . .
C10 C -0.4876(11) 0.6089(2) 0.7250(9) 0.0225(14) Uani 1 1 d . . .
H10A H -0.6042 0.6107 0.5808 0.027 Uiso 1 1 calc R . .
H10B H -0.3718 0.5840 0.7005 0.027 Uiso 1 1 calc R . .
C13 C -0.9765(11) 0.55071(19) 1.1393(9) 0.0208(14) Uani 1 1 d . . .
H13A H -0.8610 0.5466 1.2828 0.025 Uiso 1 1 calc R . .
H13B H -1.0839 0.5764 1.1707 0.025 Uiso 1 1 calc R . .
C9 C -0.3210(14) 0.6494(2) 0.7335(12) 0.0240(18) Uani 1 1 d . . .
H9A H -0.2126 0.6492 0.8836 0.029 Uiso 1 1 calc R . .
H9B H -0.2038 0.6497 0.5917 0.029 Uiso 1 1 calc R . .
C4 C -0.0073(13) 0.8797(2) 0.6082(10) 0.0260(15) Uani 1 1 d . . .
H4 H 0.0992 0.9041 0.5825 0.031 Uiso 1 1 calc R . .
C12 C -0.8080(11) 0.5599(2) 0.9191(9) 0.0201(13) Uani 1 1 d . . .
H12A H -0.6888 0.5354 0.8942 0.024 Uiso 1 1 calc R . .
H12B H -0.9204 0.5623 0.7723 0.024 Uiso 1 1 calc R . .
C19 C -1.1519(11) 0.4839(2) 0.9286(9) 0.0204(14) Uani 1 1 d . . .
H19 H -1.0287 0.4877 0.8028 0.024 Uiso 1 1 calc R . .
C11 C -0.6510(11) 0.6003(2) 0.9457(9) 0.0199(14) Uani 1 1 d . . .
H11A H -0.5368 0.5978 1.0913 0.024 Uiso 1 1 calc R . .
H11B H -0.7696 0.6248 0.9715 0.024 Uiso 1 1 calc R . .
C1 C -0.3211(13) 0.8081(2) 0.6835(11) 0.0204(17) Uani 1 1 d . . .
C17 C -1.5028(12) 0.4430(2) 1.0981(9) 0.0225(14) Uani 1 1 d . . .
H17 H -1.6182 0.4193 1.0910 0.027 Uiso 1 1 calc R . .
C14 C -1.1554(10) 0.5122(2) 1.1208(9) 0.0184(13) Uani 1 1 d . . .
C2 C -0.1251(11) 0.8197(2) 0.8530(9) 0.0217(14) Uani 1 1 d . . .
H2 H -0.0998 0.8030 0.9963 0.026 Uiso 1 1 calc R . .
C15 C -1.3359(11) 0.5051(2) 1.3039(9) 0.0202(14) Uani 1 1 d . . .
H15 H -1.3400 0.5239 1.4400 0.024 Uiso 1 1 calc R . .
C5 C -0.1975(13) 0.8691(2) 0.4418(10) 0.0277(16) Uani 1 1 d . . .
H5 H -0.2220 0.8863 0.3002 0.033 Uiso 1 1 calc R . .
C18 C -1.3244(12) 0.4501(2) 0.9155(9) 0.0217(14) Uani 1 1 d . . .
H18 H -1.3207 0.4313 0.7789 0.026 Uiso 1 1 calc R . .
C3 C 0.0284(12) 0.8546(2) 0.8127(10) 0.0249(15) Uani 1 1 d . . .
H3 H 0.1612 0.8617 0.9271 0.030 Uiso 1 1 calc R . .
C6 C -0.3529(12) 0.8339(2) 0.4786(9) 0.0235(15) Uani 1 1 d . . .
H6 H -0.4841 0.8271 0.3621 0.028 Uiso 1 1 calc R . .
 
 
_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
N1 C7 1.484(11) . ?
N1 C8 1.493(11) . ?
N1 H1A 0.9200 . ?
N1 H1B 0.9200 . ?
C8 C9 1.494(12) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C7 C1 1.520(12) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C16 C15 1.376(8) . ?
C16 C17 1.384(8) . ?
C16 H16 0.9500 . ?
C10 C11 1.506(7) . ?
C10 C9 1.527(10) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C13 C14 1.517(8) . ?
C13 C12 1.522(7) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C4 C5 1.373(9) . ?
C4 C3 1.378(8) . ?
C4 H4 0.9500 . ?
C12 C11 1.504(8) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C19 C14 1.375(8) . ?
C19 C18 1.381(8) . ?
C19 H19 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C1 C6 1.390(9) . ?
C1 C2 1.413(9) . ?
C17 C18 1.385(8) . ?
C17 H17 0.9500 . ?
C14 C15 1.393(7) . ?
C2 C3 1.366(9) . ?
C2 H2 0.9500 . ?
C15 H15 0.9500 . ?
C5 C6 1.376(9) . ?
C5 H5 0.9500 . ?
C18 H18 0.9500 . ?
C3 H3 0.9500 . ?
C6 H6 0.9500 . ?
 
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 113.6(5) . . ?
C7 N1 H1A 108.9 . . ?
C8 N1 H1A 108.9 . . ?
C7 N1 H1B 108.9 . . ?
C8 N1 H1B 108.9 . . ?
H1A N1 H1B 107.7 . . ?
C9 C8 N1 112.7(6) . . ?
C9 C8 H8A 109.1 . . ?
N1 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
N1 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
N1 C7 C1 110.8(6) . . ?
N1 C7 H7A 109.5 . . ?
C1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C15 C16 C17 120.6(5) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C11 C10 C9 116.2(5) . . ?
C11 C10 H10A 108.2 . . ?
C9 C10 H10A 108.2 . . ?
C11 C10 H10B 108.2 . . ?
C9 C10 H10B 108.2 . . ?
H10A C10 H10B 107.4 . . ?
C14 C13 C12 116.6(4) . . ?
C14 C13 H13A 108.1 . . ?
C12 C13 H13A 108.1 . . ?
C14 C13 H13B 108.1 . . ?
C12 C13 H13B 108.1 . . ?
H13A C13 H13B 107.3 . . ?
C8 C9 C10 111.2(6) . . ?
C8 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C5 C4 C3 119.6(6) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C11 C12 C13 113.0(4) . . ?
C11 C12 H12A 109.0 . . ?
C13 C12 H12A 109.0 . . ?
C11 C12 H12B 109.0 . . ?
C13 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C14 C19 C18 121.1(5) . . ?
C14 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C12 C11 C10 112.1(5) . . ?
C12 C11 H11A 109.2 . . ?
C10 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
C10 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C6 C1 C2 117.5(6) . . ?
C6 C1 C7 122.1(6) . . ?
C2 C1 C7 120.4(6) . . ?
C16 C17 C18 118.1(6) . . ?
C16 C17 H17 120.9 . . ?
C18 C17 H17 120.9 . . ?
C19 C14 C15 117.8(5) . . ?
C19 C14 C13 123.1(5) . . ?
C15 C14 C13 119.1(5) . . ?
C3 C2 C1 120.6(5) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C16 C15 C14 121.4(5) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C4 C5 C6 120.4(5) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C19 C18 C17 121.1(5) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C2 C3 C4 120.8(6) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C6 C1 121.1(6) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
 
_diffrn_measured_fraction_theta_max    0.875
_diffrn_reflns_theta_full              25.02
_diffrn_measured_fraction_theta_full   0.875
_refine_diff_density_max    0.678
_refine_diff_density_min   -0.574
_refine_diff_density_rms    0.083
