data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;

;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C21 H35 N2, 0.5(H2 O), Br'
_chemical_formula_sum
 'C21 H36 Br N2 O0.50'
_chemical_formula_weight          404.43
 
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            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                    8.7824(2)
_cell_length_b                    9.2084(3)
_cell_length_c                    14.4412(5)
_cell_angle_alpha                 76.4020(10)
_cell_angle_beta                  77.2200(10)
_cell_angle_gamma                 75.718(2)
_cell_volume                      1083.43(6)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     18925
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       26.02
 
_exptl_crystal_description        Plate
_exptl_crystal_colour             Colourless
_exptl_crystal_size_max           0.15
_exptl_crystal_size_mid           0.10
_exptl_crystal_size_min           0.04
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.240
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              430
_exptl_absorpt_coefficient_mu     1.905
_exptl_absorpt_correction_type    Multi-scan
_exptl_absorpt_correction_T_min   0.7632
_exptl_absorpt_correction_T_max   0.9277
_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          'Bruker Nonius Rotating Anode'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'Bruker Nonius Kappa CCD Area detector'
_diffrn_measurement_method        'φ and ω scans to fill the asymmetric unit'
_diffrn_detector_area_resol_mean  '9.091 pixels mm^1^'
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             7097
_diffrn_reflns_av_R_equivalents   0.0310
_diffrn_reflns_av_sigmaI/netI     0.0480
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -10
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_l_min        -17
_diffrn_reflns_limit_l_max        17
_diffrn_reflns_theta_min          2.93
_diffrn_reflns_theta_max          25.03
_reflns_number_total              3813
_reflns_number_gt                 3006
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        'COLLECT (Hooft, 1998)'
_computing_cell_refinement        'DENZO (Otwinowski and MInor, 1997)'
_computing_data_reduction         'DENZO, COLLECT, MAXUS (Mackay et al., 1998)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'CAMERON (Watkin, et al., 1993)'
_computing_publication_material   'WINGX (Farrugia, 1998)'
 
_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)+(0.0196P)²+2.3784P] 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        0.0046(10)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          3813
_refine_ls_number_parameters      237
_refine_ls_number_restraints      3
_refine_ls_R_factor_all           0.0685
_refine_ls_R_factor_gt            0.0490
_refine_ls_wR_factor_ref          0.1163
_refine_ls_wR_factor_gt           0.1056
_refine_ls_goodness_of_fit_ref    1.097
_refine_ls_restrained_S_all       1.097
_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 0.5662(6) 0.9123(5) 0.3330(3) 0.0480(11) Uani 1 1 d . . .
H1A H 0.4566 0.9624 0.3557 0.072 Uiso 1 1 calc R . .
H1B H 0.5750 0.8946 0.2676 0.072 Uiso 1 1 calc R . .
H1C H 0.6394 0.9778 0.3322 0.072 Uiso 1 1 calc R . .
C2 C 0.6092(5) 0.7609(5) 0.4004(3) 0.0397(10) Uani 1 1 d . . .
H2A H 0.7211 0.7123 0.3782 0.048 Uiso 1 1 calc R . .
H2B H 0.5402 0.6926 0.3973 0.048 Uiso 1 1 calc R . .
C3 C 0.5903(5) 0.7781(4) 0.5049(3) 0.0372(9) Uani 1 1 d . . .
H3A H 0.6607 0.8453 0.5079 0.045 Uiso 1 1 calc R . .
H3B H 0.4789 0.8290 0.5263 0.045 Uiso 1 1 calc R . .
C4 C 0.6295(5) 0.6282(4) 0.5747(3) 0.0352(9) Uani 1 1 d . . .
H4A H 0.7407 0.5770 0.5533 0.042 Uiso 1 1 calc R . .
H4B H 0.5587 0.5611 0.5722 0.042 Uiso 1 1 calc R . .
C5 C 0.6111(5) 0.6468(4) 0.6787(3) 0.0364(9) Uani 1 1 d . . .
H5A H 0.6868 0.7085 0.6820 0.044 Uiso 1 1 calc R . .
H5B H 0.5018 0.7034 0.6990 0.044 Uiso 1 1 calc R . .
C6 C 0.6410(5) 0.4955(4) 0.7488(3) 0.0342(9) Uani 1 1 d . . .
H6A H 0.5643 0.4346 0.7459 0.041 Uiso 1 1 calc R . .
H6B H 0.7497 0.4383 0.7278 0.041 Uiso 1 1 calc R . .
C7 C 0.6253(4) 0.5125(5) 0.8527(3) 0.0352(9) Uani 1 1 d . . .
H7A H 0.5222 0.5808 0.8715 0.042 Uiso 1 1 calc R . .
H7B H 0.6257 0.4115 0.8958 0.042 Uiso 1 1 calc R . .
C8 C 0.9122(4) 0.4956(4) 0.8673(3) 0.0290(8) Uani 1 1 d . . .
C9 C 0.9824(4) 0.3447(4) 0.8641(3) 0.0333(9) Uani 1 1 d . . .
H9 H 0.9237 0.2744 0.8582 0.040 Uiso 1 1 calc R . .
C10 C 1.1416(4) 0.3020(4) 0.8700(3) 0.0356(9) Uani 1 1 d . . .
H10 H 1.1950 0.1996 0.8670 0.043 Uiso 1 1 calc R . .
C11 C 1.2276(4) 0.4051(4) 0.8803(3) 0.0359(9) Uani 1 1 d . . .
H11 H 1.3375 0.3702 0.8846 0.043 Uiso 1 1 calc R . .
C12 C 1.1581(4) 0.5551(4) 0.8844(3) 0.0331(9) Uani 1 1 d . . .
H12 H 1.2166 0.6248 0.8913 0.040 Uiso 1 1 calc R . .
C13 C 0.9980(4) 0.5984(4) 0.8779(3) 0.0309(8) Uani 1 1 d . . .
C14 C 0.9290(5) 0.8778(4) 0.8908(3) 0.0368(9) Uani 1 1 d . . .
H14A H 1.0026 0.8532 0.9378 0.044 Uiso 1 1 calc R . .
H14B H 0.8303 0.9461 0.9162 0.044 Uiso 1 1 calc R . .
C15 C 1.0055(5) 0.9594(4) 0.7954(3) 0.0388(9) Uani 1 1 d . . .
H15A H 1.0984 0.8871 0.7680 0.047 Uiso 1 1 calc R . .
H15B H 1.0459 1.0434 0.8074 0.047 Uiso 1 1 calc R . .
C16 C 0.8964(5) 1.0252(4) 0.7210(3) 0.0398(10) Uani 1 1 d . . .
H16A H 0.8651 0.9405 0.7033 0.048 Uiso 1 1 calc R . .
H16B H 0.7982 1.0898 0.7502 0.048 Uiso 1 1 calc R . .
C17 C 0.9728(5) 1.1195(5) 0.6303(3) 0.0406(10) Uani 1 1 d . . .
H17A H 1.0727 1.0553 0.6024 0.049 Uiso 1 1 calc R . .
H17B H 1.0020 1.2052 0.6482 0.049 Uiso 1 1 calc R . .
C18 C 0.8686(5) 1.1839(4) 0.5534(3) 0.0390(9) Uani 1 1 d . . .
H18A H 0.8409 1.0982 0.5346 0.047 Uiso 1 1 calc R . .
H18B H 0.7681 1.2470 0.5814 0.047 Uiso 1 1 calc R . .
C19 C 0.9457(5) 1.2798(5) 0.4638(3) 0.0433(10) Uani 1 1 d . . .
H19A H 1.0469 1.2172 0.4361 0.052 Uiso 1 1 calc R . .
H19B H 0.9719 1.3665 0.4823 0.052 Uiso 1 1 calc R . .
C20 C 0.8413(5) 1.3416(5) 0.3869(3) 0.0495(11) Uani 1 1 d . . .
H20A H 0.8197 1.2565 0.3655 0.074 Uiso 1 1 calc R . .
H20B H 0.8963 1.4052 0.3317 0.074 Uiso 1 1 calc R . .
H20C H 0.7405 1.4032 0.4137 0.074 Uiso 1 1 calc R . .
C21 C 0.7478(5) 0.7173(4) 0.8744(3) 0.0344(9) Uani 1 1 d . . .
H21 H 0.6536 0.7949 0.8755 0.041 Uiso 1 1 calc R . .
N1 N 0.7560(4) 0.5755(3) 0.8656(2) 0.0325(7) Uani 1 1 d . . .
N2 N 0.8895(4) 0.7361(3) 0.8817(2) 0.0318(7) Uani 1 1 d . . .
Br1 Br 0.33259(5) 0.84913(5) 0.94537(4) 0.0539(2) Uani 1 1 d . . .
O1W O 0.4586(6) 0.8764(6) 0.1228(3) 0.0295(11) Uani 0.50 1 d PD . .
H2W H 0.520(5) 0.947(4) 0.108(4) 0.03(2) Uiso 0.50 1 d PD . .
H1W H 0.424(9) 0.866(8) 0.071(3) 0.05(3) 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 C2 1.516(6) . ?
C2 C3 1.522(5) . ?
C3 C4 1.518(5) . ?
C4 C5 1.520(5) . ?
C5 C6 1.519(5) . ?
C6 C7 1.519(5) . ?
C7 N1 1.470(5) . ?
C8 C9 1.381(5) . ?
C8 N1 1.390(5) . ?
C8 C13 1.399(5) . ?
C9 C10 1.372(5) . ?
C10 C11 1.401(5) . ?
C11 C12 1.375(5) . ?
C12 C13 1.381(5) . ?
C13 N2 1.390(5) . ?
C14 N2 1.470(5) . ?
C14 C15 1.505(6) . ?
C15 C16 1.518(6) . ?
C16 C17 1.511(6) . ?
C17 C18 1.515(6) . ?
C18 C19 1.511(6) . ?
C19 C20 1.514(6) . ?
C21 N1 1.325(5) . ?
C21 N2 1.327(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
C1 C2 C3 112.7(3) . . ?
C4 C3 C2 114.0(3) . . ?
C3 C4 C5 113.6(3) . . ?
C6 C5 C4 113.1(3) . . ?
C7 C6 C5 113.6(3) . . ?
N1 C7 C6 111.6(3) . . ?
C9 C8 N1 131.6(3) . . ?
C9 C8 C13 121.8(3) . . ?
N1 C8 C13 106.6(3) . . ?
C10 C9 C8 116.3(3) . . ?
C9 C10 C11 121.8(3) . . ?
C12 C11 C10 122.1(4) . . ?
C11 C12 C13 116.0(3) . . ?
C12 C13 N2 132.0(3) . . ?
C12 C13 C8 121.9(3) . . ?
N2 C13 C8 106.1(3) . . ?
N2 C14 C15 111.9(3) . . ?
C14 C15 C16 114.9(3) . . ?
C17 C16 C15 113.1(3) . . ?
C16 C17 C18 114.4(3) . . ?
C19 C18 C17 113.9(3) . . ?
C18 C19 C20 113.4(4) . . ?
N1 C21 N2 110.6(3) . . ?
C21 N1 C8 108.3(3) . . ?
C21 N1 C7 126.6(3) . . ?
C8 N1 C7 125.1(3) . . ?
C21 N2 C13 108.5(3) . . ?
C21 N2 C14 126.7(3) . . ?
C13 N2 C14 124.8(3) . . ?
 
loop_
 _geom_hbond_atom_site_label_D
 _geom_hbond_atom_site_label_H
 _geom_hbond_atom_site_label_A
 _geom_hbond_distance_DH
 _geom_hbond_distance_HA
 _geom_hbond_distance_DA
 _geom_hbond_angle_DHA
 _geom_hbond_site_symmetry_A
O1W H2W Br1  0.9000(10) 2.427(8) 3.323(5) 173(5) 2_676
O1W H1W Br1  0.9000(10) 2.190(6) 3.090(5) 178(8) 1_554
 
_diffrn_measured_fraction_theta_max    0.999
_diffrn_reflns_theta_full              25.03
_diffrn_measured_fraction_theta_full   0.999
_refine_diff_density_max    1.164
_refine_diff_density_min   -1.872
_refine_diff_density_rms    0.072
