data_03src0049
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C23 H39 N2, H2 O, Br '
_chemical_formula_sum
 'C23 H41 Br N2 O'
_chemical_formula_weight          441.49
 
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'
 'O'  'O'   0.0106   0.0060
 '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            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                    9.0890(2)
_cell_length_b                    9.1411(3)
_cell_length_c                    15.9877(5)
_cell_angle_alpha                 77.5730(10)
_cell_angle_beta                  76.5140(10)
_cell_angle_gamma                 77.964(2)
_cell_volume                      1243.77(6)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     17182
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.38
_exptl_crystal_size_mid           0.16
_exptl_crystal_size_min           0.14
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.179
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              472
_exptl_absorpt_coefficient_mu     1.666
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.5701
_exptl_absorpt_correction_T_max   0.8002
_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             21830
_diffrn_reflns_av_R_equivalents   0.0719
_diffrn_reflns_av_sigmaI/netI     0.0616
_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        -20
_diffrn_reflns_limit_l_max        20
_diffrn_reflns_theta_min          3.00
_diffrn_reflns_theta_max          27.50
_reflns_number_total              5668
_reflns_number_gt                 3888
_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)+(0.0338P)²+0.4166P] 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        0.0114(17)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          5668
_refine_ls_number_parameters      255
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0819
_refine_ls_R_factor_gt            0.0467
_refine_ls_wR_factor_ref          0.1042
_refine_ls_wR_factor_gt           0.0912
_refine_ls_goodness_of_fit_ref    1.020
_refine_ls_restrained_S_all       1.020
_refine_ls_shift/su_max           0.040
_refine_ls_shift/su_mean          0.002
 
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
O1 O 0.5455(3) 0.6451(3) -0.11183(19) 0.1007(8) Uani 1 1 d . . .
H1O H 0.583(7) 0.641(7) -0.053(4) 0.20(2) Uiso 1 1 d . . .
H2O H 0.474(7) 0.562(7) -0.100(4) 0.20(2) Uiso 1 1 d . . .
C1 C 0.6075(5) 1.3277(5) -0.6898(2) 0.1064(13) Uani 1 1 d . . .
H1A H 0.7098 1.2691 -0.7065 0.160 Uiso 1 1 calc R . .
H1B H 0.5974 1.4253 -0.7298 0.160 Uiso 1 1 calc R . .
H1C H 0.5294 1.2707 -0.6930 0.160 Uiso 1 1 calc R . .
C2 C 0.5860(4) 1.3554(4) -0.5978(2) 0.0791(9) Uani 1 1 d . . .
H2A H 0.6537 1.4272 -0.5975 0.095 Uiso 1 1 calc R . .
H2B H 0.4787 1.4047 -0.5794 0.095 Uiso 1 1 calc R . .
C3 C 0.6197(4) 1.2147(3) -0.5319(2) 0.0691(8) Uani 1 1 d . . .
H3A H 0.7269 1.1654 -0.5505 0.083 Uiso 1 1 calc R . .
H3B H 0.5519 1.1430 -0.5323 0.083 Uiso 1 1 calc R . .
C4 C 0.5987(4) 1.2410(3) -0.4390(2) 0.0673(8) Uani 1 1 d . . .
H4A H 0.6691 1.3098 -0.4381 0.081 Uiso 1 1 calc R . .
H4B H 0.4925 1.2931 -0.4209 0.081 Uiso 1 1 calc R . .
C5 C 0.6279(4) 1.0986(3) -0.37326(19) 0.0662(8) Uani 1 1 d . . .
H5A H 0.7333 1.0451 -0.3920 0.079 Uiso 1 1 calc R . .
H5B H 0.5558 1.0309 -0.3729 0.079 Uiso 1 1 calc R . .
C6 C 0.6104(3) 1.1266(3) -0.28086(19) 0.0624(7) Uani 1 1 d . . .
H6A H 0.6847 1.1917 -0.2806 0.075 Uiso 1 1 calc R . .
H6B H 0.5059 1.1823 -0.2625 0.075 Uiso 1 1 calc R . .
C7 C 0.6359(3) 0.9824(3) -0.21566(18) 0.0567(7) Uani 1 1 d . . .
H7A H 0.7396 0.9258 -0.2350 0.068 Uiso 1 1 calc R . .
H7B H 0.5605 0.9182 -0.2155 0.068 Uiso 1 1 calc R . .
C8 C 0.6219(3) 1.0071(3) -0.12266(17) 0.0530(6) Uani 1 1 d . . .
H8A H 0.5243 1.0752 -0.1055 0.064 Uiso 1 1 calc R . .
H8B H 0.6197 0.9086 -0.0822 0.064 Uiso 1 1 calc R . .
C9 C 0.7495(3) 1.2203(3) -0.11422(16) 0.0468(6) Uani 1 1 d . . .
H9 H 0.6611 1.2970 -0.1145 0.056 Uiso 1 1 calc R . .
C10 C 0.9003(3) 0.9980(3) -0.11432(15) 0.0412(5) Uani 1 1 d . . .
C11 C 0.9633(3) 0.8443(3) -0.11226(16) 0.0501(6) Uani 1 1 d . . .
H11 H 0.9033 0.7707 -0.1122 0.060 Uiso 1 1 calc R . .
C12 C 1.1167(3) 0.8060(3) -0.11028(17) 0.0527(6) Uani 1 1 d . . .
H12 H 1.1647 0.7031 -0.1098 0.063 Uiso 1 1 calc R . .
C13 C 1.2047(3) 0.9137(3) -0.10898(17) 0.0522(6) Uani 1 1 d . . .
H13 H 1.3105 0.8815 -0.1075 0.063 Uiso 1 1 calc R . .
C14 C 1.1430(3) 1.0652(3) -0.10980(16) 0.0484(6) Uani 1 1 d . . .
H14 H 1.2028 1.1380 -0.1084 0.058 Uiso 1 1 calc R . .
C15 C 0.9880(3) 1.1048(2) -0.11283(15) 0.0399(5) Uani 1 1 d . . .
C16 C 0.9321(3) 1.3905(3) -0.11280(18) 0.0528(6) Uani 1 1 d . . .
H16A H 1.0060 1.3740 -0.0736 0.063 Uiso 1 1 calc R . .
H16B H 0.8398 1.4600 -0.0896 0.063 Uiso 1 1 calc R . .
C17 C 1.0036(3) 1.4639(3) -0.20330(19) 0.0570(7) Uani 1 1 d . . .
H17A H 1.0899 1.3898 -0.2281 0.068 Uiso 1 1 calc R . .
H17B H 1.0468 1.5515 -0.1979 0.068 Uiso 1 1 calc R . .
C18 C 0.8948(3) 1.5190(3) -0.2673(2) 0.0615(7) Uani 1 1 d . . .
H18A H 0.8635 1.4299 -0.2801 0.074 Uiso 1 1 calc R . .
H18B H 0.8014 1.5820 -0.2397 0.074 Uiso 1 1 calc R . .
C19 C 0.9656(3) 1.6108(3) -0.3523(2) 0.0666(8) Uani 1 1 d . . .
H19A H 0.9942 1.7010 -0.3391 0.080 Uiso 1 1 calc R . .
H19B H 1.0611 1.5486 -0.3784 0.080 Uiso 1 1 calc R . .
C20 C 0.8634(3) 1.6638(3) -0.4190(2) 0.0674(8) Uani 1 1 d . . .
H20A H 0.7675 1.7259 -0.3929 0.081 Uiso 1 1 calc R . .
H20B H 0.8353 1.5738 -0.4326 0.081 Uiso 1 1 calc R . .
C21 C 0.9359(4) 1.7566(4) -0.5035(2) 0.0705(8) Uani 1 1 d . . .
H21A H 0.9614 1.8479 -0.4899 0.085 Uiso 1 1 calc R . .
H21B H 1.0332 1.6955 -0.5285 0.085 Uiso 1 1 calc R . .
C22 C 0.8371(4) 1.8066(4) -0.5714(2) 0.0823(10) Uani 1 1 d . . .
H22A H 0.7391 1.8669 -0.5464 0.099 Uiso 1 1 calc R . .
H22B H 0.8129 1.7156 -0.5861 0.099 Uiso 1 1 calc R . .
C23 C 0.9123(5) 1.9015(5) -0.6550(2) 0.1067(14) Uani 1 1 d . . .
H23A H 0.9384 1.9909 -0.6409 0.160 Uiso 1 1 calc R . .
H23B H 0.8409 1.9343 -0.6954 0.160 Uiso 1 1 calc R . .
H23C H 1.0058 1.8403 -0.6823 0.160 Uiso 1 1 calc R . .
N1 N 0.7515(2) 1.0746(2) -0.11518(13) 0.0449(5) Uani 1 1 d . . .
N2 N 0.8885(2) 1.2435(2) -0.11289(13) 0.0432(5) Uani 1 1 d . . .
Br1 Br 0.66511(3) 0.63091(3) 0.06920(2) 0.06303(14) Uani 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
O1 H1O 1.07(6) . ?
O1 H2O 1.06(6) . ?
C1 C2 1.508(5) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.504(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.518(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.505(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.519(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.507(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.524(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N1 1.478(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N2 1.329(3) . ?
C9 N1 1.331(3) . ?
C9 H9 0.9500 . ?
C10 N1 1.389(3) . ?
C10 C15 1.390(3) . ?
C10 C11 1.399(3) . ?
C11 C12 1.371(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.398(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.380(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.389(3) . ?
C14 H14 0.9500 . ?
C15 N2 1.395(3) . ?
C16 N2 1.479(3) . ?
C16 C17 1.514(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.524(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.513(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.513(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.518(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.504(4) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.526(5) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
 
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
H1O O1 H2O 108(4) . . ?
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 114.5(3) . . ?
C3 C2 H2A 108.6 . . ?
C1 C2 H2A 108.6 . . ?
C3 C2 H2B 108.6 . . ?
C1 C2 H2B 108.6 . . ?
H2A C2 H2B 107.6 . . ?
C2 C3 C4 115.0(3) . . ?
C2 C3 H3A 108.5 . . ?
C4 C3 H3A 108.5 . . ?
C2 C3 H3B 108.5 . . ?
C4 C3 H3B 108.5 . . ?
H3A C3 H3B 107.5 . . ?
C5 C4 C3 114.5(2) . . ?
C5 C4 H4A 108.6 . . ?
C3 C4 H4A 108.6 . . ?
C5 C4 H4B 108.6 . . ?
C3 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
C4 C5 C6 114.1(2) . . ?
C4 C5 H5A 108.7 . . ?
C6 C5 H5A 108.7 . . ?
C4 C5 H5B 108.7 . . ?
C6 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
C7 C6 C5 113.2(2) . . ?
C7 C6 H6A 108.9 . . ?
C5 C6 H6A 108.9 . . ?
C7 C6 H6B 108.9 . . ?
C5 C6 H6B 108.9 . . ?
H6A C6 H6B 107.8 . . ?
C6 C7 C8 114.3(2) . . ?
C6 C7 H7A 108.7 . . ?
C8 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
C8 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
N1 C8 C7 111.2(2) . . ?
N1 C8 H8A 109.4 . . ?
C7 C8 H8A 109.4 . . ?
N1 C8 H8B 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
N2 C9 N1 110.5(2) . . ?
N2 C9 H9 124.7 . . ?
N1 C9 H9 124.7 . . ?
N1 C10 C15 106.95(19) . . ?
N1 C10 C11 131.3(2) . . ?
C15 C10 C11 121.7(2) . . ?
C12 C11 C10 116.1(2) . . ?
C12 C11 H11 121.9 . . ?
C10 C11 H11 121.9 . . ?
C11 C12 C13 122.0(2) . . ?
C11 C12 H12 119.0 . . ?
C13 C12 H12 119.0 . . ?
C14 C13 C12 122.2(2) . . ?
C14 C13 H13 118.9 . . ?
C12 C13 H13 118.9 . . ?
C13 C14 C15 115.9(2) . . ?
C13 C14 H14 122.0 . . ?
C15 C14 H14 122.0 . . ?
C14 C15 C10 122.0(2) . . ?
C14 C15 N2 131.7(2) . . ?
C10 C15 N2 106.27(19) . . ?
N2 C16 C17 112.1(2) . . ?
N2 C16 H16A 109.2 . . ?
C17 C16 H16A 109.2 . . ?
N2 C16 H16B 109.2 . . ?
C17 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C16 C17 C18 115.2(2) . . ?
C16 C17 H17A 108.5 . . ?
C18 C17 H17A 108.5 . . ?
C16 C17 H17B 108.5 . . ?
C18 C17 H17B 108.5 . . ?
H17A C17 H17B 107.5 . . ?
C19 C18 C17 112.9(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 . . ?
C20 C19 C18 114.8(2) . . ?
C20 C19 H19A 108.6 . . ?
C18 C19 H19A 108.6 . . ?
C20 C19 H19B 108.6 . . ?
C18 C19 H19B 108.6 . . ?
H19A C19 H19B 107.5 . . ?
C19 C20 C21 114.0(3) . . ?
C19 C20 H20A 108.7 . . ?
C21 C20 H20A 108.7 . . ?
C19 C20 H20B 108.7 . . ?
C21 C20 H20B 108.7 . . ?
H20A C20 H20B 107.6 . . ?
C22 C21 C20 114.6(3) . . ?
C22 C21 H21A 108.6 . . ?
C20 C21 H21A 108.6 . . ?
C22 C21 H21B 108.6 . . ?
C20 C21 H21B 108.6 . . ?
H21A C21 H21B 107.6 . . ?
C21 C22 C23 113.3(3) . . ?
C21 C22 H22A 108.9 . . ?
C23 C22 H22A 108.9 . . ?
C21 C22 H22B 108.9 . . ?
C23 C22 H22B 108.9 . . ?
H22A C22 H22B 107.7 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C9 N1 C10 108.06(19) . . ?
C9 N1 C8 126.4(2) . . ?
C10 N1 C8 125.4(2) . . ?
C9 N2 C15 108.20(19) . . ?
C9 N2 C16 126.4(2) . . ?
C15 N2 C16 125.4(2) . . ?
 
_diffrn_measured_fraction_theta_max    0.991
_diffrn_reflns_theta_full              27.50
_diffrn_measured_fraction_theta_full   0.991
_refine_diff_density_max    0.286
_refine_diff_density_min   -0.377
_refine_diff_density_rms    0.048
