data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 Dr. C. Butts
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C25 H44 Br N2 O0.50'
_chemical_formula_weight          460.53
 
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                    17.5547(10)
_cell_length_b                    8.8674(6)
_cell_length_c                    17.7449(12)
_cell_angle_alpha                 90.00
_cell_angle_beta                  110.858(2)
_cell_angle_gamma                 90.00
_cell_volume                      2581.2(3)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     2825
_cell_measurement_theta_min       2.910
_cell_measurement_theta_max       27.485
 
_exptl_crystal_description        Block
_exptl_crystal_colour             Colourless
_exptl_crystal_size_max           0.45
_exptl_crystal_size_mid           0.25
_exptl_crystal_size_min           0.18
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.185
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              988
_exptl_absorpt_coefficient_mu     1.607
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.5316
_exptl_absorpt_correction_T_max   0.7608
_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             12586
_diffrn_reflns_av_R_equivalents   0.0588
_diffrn_reflns_av_sigmaI/netI     0.0663
_diffrn_reflns_limit_h_min        -21
_diffrn_reflns_limit_h_max        21
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_l_min        -22
_diffrn_reflns_limit_l_max        22
_diffrn_reflns_theta_min          3.07
_diffrn_reflns_theta_max          27.39
_reflns_number_total              4135
_reflns_number_gt                 3111
_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)+(0.0089P)²+15.3942P] 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          4135
_refine_ls_number_parameters      270
_refine_ls_number_restraints      3
_refine_ls_R_factor_all           0.1165
_refine_ls_R_factor_gt            0.0825
_refine_ls_wR_factor_ref          0.1680
_refine_ls_wR_factor_gt           0.1548
_refine_ls_goodness_of_fit_ref    1.152
_refine_ls_restrained_S_all       1.152
_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
C1 C 0.8872(3) 0.1756(9) 0.5439(4) 0.0342(17) Uani 1 1 d . . .
H1 H 0.8856 0.2484 0.5826 0.041 Uiso 1 1 calc R . .
C2 C 0.8860(3) 0.0720(8) 0.4307(4) 0.0316(16) Uani 1 1 d . . .
C3 C 0.8970(3) -0.0445(9) 0.4873(4) 0.0342(16) Uani 1 1 d . . .
C4 C 0.9083(4) -0.1934(8) 0.4723(5) 0.0389(18) Uani 1 1 d . . .
H4 H 0.9158 -0.2703 0.5115 0.047 Uiso 1 1 calc R . .
C5 C 0.9082(4) -0.2226(10) 0.3956(5) 0.051(2) Uani 1 1 d . . .
H5 H 0.9153 -0.3238 0.3818 0.061 Uiso 1 1 calc R . .
C6 C 0.8980(4) -0.1112(11) 0.3380(5) 0.050(2) Uani 1 1 d . . .
H6 H 0.8993 -0.1382 0.2866 0.061 Uiso 1 1 calc R . .
C7 C 0.8862(4) 0.0385(10) 0.3534(4) 0.0421(19) Uani 1 1 d . . .
H7 H 0.8785 0.1146 0.3137 0.050 Uiso 1 1 calc R . .
C8 C 0.8711(4) 0.3569(8) 0.4311(4) 0.0372(17) Uani 1 1 d . . .
H8A H 0.9102 0.3689 0.4028 0.045 Uiso 1 1 calc R . .
H8B H 0.8839 0.4343 0.4741 0.045 Uiso 1 1 calc R . .
C9 C 0.7843(3) 0.3815(8) 0.3714(4) 0.0354(17) Uani 1 1 d . . .
H9A H 0.7823 0.4775 0.3422 0.042 Uiso 1 1 calc R . .
H9B H 0.7701 0.2989 0.3312 0.042 Uiso 1 1 calc R . .
C10 C 0.7213(4) 0.3867(9) 0.4123(4) 0.0401(18) Uani 1 1 d . . .
H10A H 0.7352 0.4701 0.4520 0.048 Uiso 1 1 calc R . .
H10B H 0.7240 0.2913 0.4421 0.048 Uiso 1 1 calc R . .
C11 C 0.6339(4) 0.4093(9) 0.3527(4) 0.0383(17) Uani 1 1 d . . .
H11A H 0.6322 0.4994 0.3192 0.046 Uiso 1 1 calc R . .
H11B H 0.6179 0.3209 0.3164 0.046 Uiso 1 1 calc R . .
C12 C 0.5730(4) 0.4291(9) 0.3953(4) 0.0423(19) Uani 1 1 d . . .
H12A H 0.5897 0.5168 0.4321 0.051 Uiso 1 1 calc R . .
H12B H 0.5749 0.3386 0.4286 0.051 Uiso 1 1 calc R . .
C13 C 0.4851(4) 0.4531(9) 0.3376(4) 0.0407(17) Uani 1 1 d . . .
H13A H 0.4835 0.5416 0.3030 0.049 Uiso 1 1 calc R . .
H13B H 0.4677 0.3638 0.3020 0.049 Uiso 1 1 calc R . .
C14 C 0.4251(4) 0.4779(9) 0.3810(4) 0.0418(18) Uani 1 1 d . . .
H14A H 0.4268 0.3893 0.4155 0.050 Uiso 1 1 calc R . .
H14B H 0.4427 0.5669 0.4167 0.050 Uiso 1 1 calc R . .
C15 C 0.3373(4) 0.5024(9) 0.3241(4) 0.044(2) Uani 1 1 d . . .
H15A H 0.3188 0.4124 0.2893 0.053 Uiso 1 1 calc R . .
H15B H 0.3354 0.5899 0.2889 0.053 Uiso 1 1 calc R . .
C16 C 0.2792(4) 0.5305(10) 0.3701(4) 0.049(2) Uani 1 1 d . . .
H16A H 0.2806 0.4436 0.4047 0.073 Uiso 1 1 calc R . .
H16B H 0.2237 0.5445 0.3315 0.073 Uiso 1 1 calc R . .
H16C H 0.2964 0.6212 0.4034 0.073 Uiso 1 1 calc R . .
C17 C 0.9046(4) -0.0478(10) 0.6349(4) 0.051(2) Uani 1 1 d . . .
H17A H 0.9246 0.0258 0.6796 0.062 Uiso 1 1 calc R . .
H17B H 0.9454 -0.1297 0.6453 0.062 Uiso 1 1 calc R . .
C18 C 0.8241(4) -0.1130(10) 0.6330(5) 0.053(2) Uani 1 1 d . . .
H18A H 0.8337 -0.1736 0.6824 0.064 Uiso 1 1 calc R . .
H18B H 0.8027 -0.1815 0.5861 0.064 Uiso 1 1 calc R . .
C19 C 0.7601(4) 0.0075(9) 0.6276(4) 0.0434(19) Uani 1 1 d . . .
H19A H 0.7491 0.0661 0.5773 0.052 Uiso 1 1 calc R . .
H19B H 0.7821 0.0778 0.6736 0.052 Uiso 1 1 calc R . .
C20 C 0.6795(4) -0.0600(9) 0.6283(4) 0.0432(19) Uani 1 1 d . . .
H20A H 0.6585 -0.1325 0.5832 0.052 Uiso 1 1 calc R . .
H20B H 0.6904 -0.1165 0.6792 0.052 Uiso 1 1 calc R . .
C21 C 0.6140(4) 0.0581(8) 0.6207(4) 0.0382(18) Uani 1 1 d . . .
H21A H 0.6045 0.1177 0.5711 0.046 Uiso 1 1 calc R . .
H21B H 0.6337 0.1280 0.6672 0.046 Uiso 1 1 calc R . .
C22 C 0.5332(4) -0.0121(8) 0.6179(4) 0.0394(18) Uani 1 1 d . . .
H22A H 0.5128 -0.0802 0.5707 0.047 Uiso 1 1 calc R . .
H22B H 0.5429 -0.0735 0.6670 0.047 Uiso 1 1 calc R . .
C23 C 0.4682(4) 0.1059(8) 0.6122(4) 0.0396(18) Uani 1 1 d . . .
H23A H 0.4591 0.1682 0.5635 0.048 Uiso 1 1 calc R . .
H23B H 0.4883 0.1731 0.6597 0.048 Uiso 1 1 calc R . .
C24 C 0.3871(4) 0.0363(9) 0.6081(4) 0.0428(18) Uani 1 1 d . . .
H24A H 0.3967 -0.0311 0.6551 0.051 Uiso 1 1 calc R . .
H24B H 0.3652 -0.0257 0.5587 0.051 Uiso 1 1 calc R . .
C25 C 0.3237(4) 0.1556(10) 0.6078(5) 0.053(2) Uani 1 1 d . . .
H25A H 0.3450 0.2173 0.6566 0.080 Uiso 1 1 calc R . .
H25B H 0.2734 0.1055 0.6063 0.080 Uiso 1 1 calc R . .
H25C H 0.3122 0.2201 0.5601 0.080 Uiso 1 1 calc R . .
N1 N 0.8804(3) 0.2079(6) 0.4672(3) 0.0298(13) Uani 1 1 d . . .
N2 N 0.8964(3) 0.0282(8) 0.5577(3) 0.0350(14) Uani 1 1 d . . .
Br1 Br 0.95801(4) 0.53122(9) 0.64669(4) 0.0426(2) Uani 1 1 d . . .
O1W O 0.9085(6) 0.2444(12) 0.7291(6) 0.047(3) Uani 0.50 1 d PD . .
H1WA H 0.954(4) 0.285(12) 0.737(9) 0.071 Uiso 0.50 1 d PD . .
H1WB H 0.875(6) 0.315(9) 0.725(10) 0.071 Uiso 0.50 1 d PD . .
 
 
_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 N2 1.329(9) . ?
C1 N1 1.353(8) . ?
C1 H1 0.9500 . ?
C2 N1 1.388(8) . ?
C2 C3 1.405(9) . ?
C2 C7 1.405(9) . ?
C3 C4 1.376(10) . ?
C3 N2 1.408(8) . ?
C4 C5 1.383(10) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(11) . ?
C5 H5 0.9500 . ?
C6 C7 1.386(11) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 N1 1.452(8) . ?
C8 C9 1.531(8) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.524(8) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.535(8) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.523(8) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.533(8) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.527(8) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.526(8) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.537(9) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 N2 1.487(8) . ?
C17 C18 1.516(10) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.529(10) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.541(9) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.525(9) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.533(9) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.524(9) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.530(9) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.533(10) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
O1W H1WA 0.841(11) . ?
O1W H1WB 0.840(10) . ?
 
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 C1 N1 110.8(6) . . ?
N2 C1 H1 124.6 . . ?
N1 C1 H1 124.6 . . ?
N1 C2 C3 108.7(6) . . ?
N1 C2 C7 131.6(7) . . ?
C3 C2 C7 119.7(7) . . ?
C4 C3 C2 124.0(7) . . ?
C4 C3 N2 131.2(7) . . ?
C2 C3 N2 104.8(6) . . ?
C3 C4 C5 114.9(7) . . ?
C3 C4 H4 122.6 . . ?
C5 C4 H4 122.6 . . ?
C4 C5 C6 123.1(8) . . ?
C4 C5 H5 118.4 . . ?
C6 C5 H5 118.4 . . ?
C7 C6 C5 121.7(7) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C6 C7 C2 116.6(7) . . ?
C6 C7 H7 121.7 . . ?
C2 C7 H7 121.7 . . ?
N1 C8 C9 111.3(5) . . ?
N1 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
N1 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C10 C9 C8 112.7(5) . . ?
C10 C9 H9A 109.0 . . ?
C8 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 C11 113.1(5) . . ?
C9 C10 H10A 109.0 . . ?
C11 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
C11 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C12 C11 C10 112.3(5) . . ?
C12 C11 H11A 109.1 . . ?
C10 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
C10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 C13 113.7(5) . . ?
C11 C12 H12A 108.8 . . ?
C13 C12 H12A 108.8 . . ?
C11 C12 H12B 108.8 . . ?
C13 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C14 C13 C12 113.2(5) . . ?
C14 C13 H13A 108.9 . . ?
C12 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C12 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C15 C14 C13 113.7(5) . . ?
C15 C14 H14A 108.8 . . ?
C13 C14 H14A 108.8 . . ?
C15 C14 H14B 108.8 . . ?
C13 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C14 C15 C16 112.1(5) . . ?
C14 C15 H15A 109.2 . . ?
C16 C15 H15A 109.2 . . ?
C14 C15 H15B 109.2 . . ?
C16 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 C17 C18 111.7(5) . . ?
N2 C17 H17A 109.3 . . ?
C18 C17 H17A 109.3 . . ?
N2 C17 H17B 109.3 . . ?
C18 C17 H17B 109.3 . . ?
H17A C17 H17B 107.9 . . ?
C17 C18 C19 113.1(7) . . ?
C17 C18 H18A 109.0 . . ?
C19 C18 H18A 109.0 . . ?
C17 C18 H18B 109.0 . . ?
C19 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C18 C19 C20 112.6(6) . . ?
C18 C19 H19A 109.1 . . ?
C20 C19 H19A 109.1 . . ?
C18 C19 H19B 109.1 . . ?
C20 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
C21 C20 C19 113.5(6) . . ?
C21 C20 H20A 108.9 . . ?
C19 C20 H20A 108.9 . . ?
C21 C20 H20B 108.9 . . ?
C19 C20 H20B 108.9 . . ?
H20A C20 H20B 107.7 . . ?
C20 C21 C22 112.6(6) . . ?
C20 C21 H21A 109.1 . . ?
C22 C21 H21A 109.1 . . ?
C20 C21 H21B 109.1 . . ?
C22 C21 H21B 109.1 . . ?
H21A C21 H21B 107.8 . . ?
C23 C22 C21 112.7(6) . . ?
C23 C22 H22A 109.1 . . ?
C21 C22 H22A 109.1 . . ?
C23 C22 H22B 109.1 . . ?
C21 C22 H22B 109.1 . . ?
H22A C22 H22B 107.8 . . ?
C22 C23 C24 112.9(6) . . ?
C22 C23 H23A 109.0 . . ?
C24 C23 H23A 109.0 . . ?
C22 C23 H23B 109.0 . . ?
C24 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
C23 C24 C25 112.6(6) . . ?
C23 C24 H24A 109.1 . . ?
C25 C24 H24A 109.1 . . ?
C23 C24 H24B 109.1 . . ?
C25 C24 H24B 109.1 . . ?
H24A C24 H24B 107.8 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C1 N1 C2 106.8(6) . . ?
C1 N1 C8 126.3(6) . . ?
C2 N1 C8 126.9(5) . . ?
C1 N2 C3 109.0(6) . . ?
C1 N2 C17 125.5(6) . . ?
C3 N2 C17 125.5(7) . . ?
H1WA O1W H1WB 106.9(18) . . ?
 
_diffrn_measured_fraction_theta_max    0.704
_diffrn_reflns_theta_full              27.39
_diffrn_measured_fraction_theta_full   0.704
_refine_diff_density_max    0.717
_refine_diff_density_min   -0.858
_refine_diff_density_rms    0.090
