data_joef101
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C21 H22 Br N O2'
_chemical_formula_weight          400.31
 
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            Orthorhombic
_symmetry_space_group_name_H-M    P2(1)2(1)2(1)
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'
 
_cell_length_a                    6.025(2)
_cell_length_b                    9.345(4)
_cell_length_c                    32.971(13)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      1856.5(13)
_cell_formula_units_Z             4
_cell_measurement_temperature     200(2)
_cell_measurement_reflns_used     1022
_cell_measurement_theta_min       2.86
_cell_measurement_theta_max       17.87
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.24
_exptl_crystal_size_mid           0.16
_exptl_crystal_size_min           0.10
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.432
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              824
_exptl_absorpt_coefficient_mu     2.228
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.6180
_exptl_absorpt_correction_T_max   0.8014
_exptl_absorpt_process_details    'SADABS (Sheldrick, 2003)'
 
_exptl_special_details
;
Data collection is performed with four batch runs at
\f = 0.00 \% (600 frames), at \f = 90.00 \%
(600 frames), at \f = 180 \% (600 frames) and
at \f = 270 \% (600 frames).
Frame width = 0.30 \& in \w. Data is
merged, corrected for decay, and treated with
multi-scan absorption corrections.
;
 
_diffrn_ambient_temperature       200(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'fine-focus sealed tube'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'Bruker AXS APEX diffractometer'
_diffrn_measurement_method        \w
_diffrn_detector_area_resol_mean  836.6
_diffrn_standards_number          0
_diffrn_standards_interval_count  0
_diffrn_standards_interval_time   0
_diffrn_standards_decay_%         1
_diffrn_reflns_number             16349
_diffrn_reflns_av_R_equivalents   0.0953
_diffrn_reflns_av_sigmaI/netI     0.1076
_diffrn_reflns_limit_h_min        -8
_diffrn_reflns_limit_h_max        7
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -44
_diffrn_reflns_limit_l_max        44
_diffrn_reflns_theta_min          2.27
_diffrn_reflns_theta_max          28.45
_reflns_number_total              4647
_reflns_number_gt                 2765
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        'SMART (Bruker, 2002)'
_computing_cell_refinement        'SAINT (Bruker, 2002)'
_computing_data_reduction         SAINT
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2001)'
_computing_publication_material   'SHELXTL (Sheldrick, 2001)'
 
_refine_special_details
;
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F^2^, conventional R-factors R are based
 on F, with F set to zero for negative F^2^. The threshold expression of
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F^2^ 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/[\s^2^(Fo^2^)+(0.0025P)^2^] where P=(Fo^2^+2Fc^2^)/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: 1943 Friedel pairs'
_refine_ls_abs_structure_Flack    -0.017(10)
_refine_ls_number_reflns          4647
_refine_ls_number_parameters      229
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1163
_refine_ls_R_factor_gt            0.0512
_refine_ls_wR_factor_ref          0.0807
_refine_ls_wR_factor_gt           0.0677
_refine_ls_goodness_of_fit_ref    1.021
_refine_ls_restrained_S_all       1.021
_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
Br Br 1.05031(7) -0.33648(5) 0.757234(12) 0.05828(16) Uani 1 1 d . . .
O1 O 1.0365(4) 0.6298(3) 0.92837(7) 0.0371(6) Uani 1 1 d . . .
O2 O 0.6826(4) 0.6675(3) 0.94487(8) 0.0495(8) Uani 1 1 d . . .
N1 N 0.8245(5) 0.1283(3) 0.90013(9) 0.0297(7) Uani 1 1 d . . .
C1 C 1.1048(6) 0.7052(4) 0.96485(11) 0.0423(11) Uani 1 1 d . . .
H1A H 1.2664 0.7170 0.9648 0.063 Uiso 1 1 calc R . .
H1B H 1.0603 0.6499 0.9888 0.063 Uiso 1 1 calc R . .
H1C H 1.0336 0.7994 0.9656 0.063 Uiso 1 1 calc R . .
C2 C 0.8180(7) 0.6140(4) 0.92276(12) 0.0340(10) Uani 1 1 d . . .
C3 C 0.7727(6) 0.5212(4) 0.88628(11) 0.0288(9) Uani 1 1 d . . .
H3A H 0.9017 0.5322 0.8674 0.035 Uiso 1 1 calc R . .
C4 C 0.5645(7) 0.5692(4) 0.86311(10) 0.0369(9) Uani 1 1 d . . .
H4A H 0.4315 0.5505 0.8799 0.044 Uiso 1 1 calc R . .
H4B H 0.5727 0.6734 0.8580 0.044 Uiso 1 1 calc R . .
C5 C 0.5420(7) 0.4908(4) 0.82298(10) 0.0516(12) Uani 1 1 d . . .
H5A H 0.4029 0.5190 0.8098 0.077 Uiso 1 1 calc R . .
H5B H 0.5412 0.3874 0.8279 0.077 Uiso 1 1 calc R . .
H5C H 0.6674 0.5155 0.8054 0.077 Uiso 1 1 calc R . .
C6 C 1.0946(6) 0.2648(4) 0.85758(10) 0.0387(10) Uani 1 1 d . . .
H6A H 1.1123 0.3620 0.8469 0.058 Uiso 1 1 calc R . .
H6B H 1.0754 0.1977 0.8350 0.058 Uiso 1 1 calc R . .
H6C H 1.2269 0.2384 0.8732 0.058 Uiso 1 1 calc R . .
C7 C 0.8946(6) 0.2591(4) 0.88459(10) 0.0277(9) Uani 1 1 d . . .
C8 C 0.7607(6) 0.3651(3) 0.89814(10) 0.0264(9) Uani 1 1 d . . .
C9 C 0.5953(6) 0.2993(3) 0.92388(10) 0.0269(9) Uani 1 1 d . . .
C10 C 0.4131(6) 0.3487(4) 0.94617(9) 0.0322(9) Uani 1 1 d . . .
H10A H 0.3813 0.4482 0.9475 0.039 Uiso 1 1 calc R . .
C11 C 0.2804(6) 0.2521(4) 0.96618(11) 0.0357(10) Uani 1 1 d . . .
H11A H 0.1561 0.2855 0.9812 0.043 Uiso 1 1 calc R . .
C12 C 0.3256(8) 0.1052(4) 0.96482(12) 0.0401(11) Uani 1 1 d . . .
H12A H 0.2313 0.0406 0.9789 0.048 Uiso 1 1 calc R . .
C13 C 0.5039(6) 0.0529(4) 0.94353(11) 0.0371(11) Uani 1 1 d . . .
H13A H 0.5343 -0.0468 0.9425 0.045 Uiso 1 1 calc R . .
C14 C 0.6377(5) 0.1506(4) 0.92366(10) 0.0279(8) Uani 1 1 d . . .
C15 C 0.9113(7) -0.0115(4) 0.88779(10) 0.0364(10) Uani 1 1 d . . .
H15A H 0.8678 -0.0837 0.9083 0.044 Uiso 1 1 calc R . .
H15B H 1.0754 -0.0071 0.8872 0.044 Uiso 1 1 calc R . .
C16 C 0.8290(6) -0.0586(4) 0.84687(11) 0.0299(9) Uani 1 1 d . . .
C17 C 0.6265(6) -0.0129(4) 0.83096(11) 0.0363(10) Uani 1 1 d . . .
H17A H 0.5381 0.0532 0.8457 0.044 Uiso 1 1 calc R . .
C18 C 0.5535(7) -0.0631(4) 0.79377(11) 0.0408(10) Uani 1 1 d . . .
H18A H 0.4160 -0.0299 0.7833 0.049 Uiso 1 1 calc R . .
C19 C 0.6760(6) -0.1605(4) 0.77168(10) 0.0384(9) Uani 1 1 d . . .
H19A H 0.6243 -0.1954 0.7463 0.046 Uiso 1 1 calc R . .
C20 C 0.8767(6) -0.2057(4) 0.78758(11) 0.0332(10) Uani 1 1 d . . .
C21 C 0.9536(6) -0.1566(4) 0.82444(9) 0.0305(8) Uani 1 1 d . . .
H21A H 1.0920 -0.1896 0.8346 0.037 Uiso 1 1 calc R . .
 
loop_
 _atom_site_aniso_label
 _atom_site_aniso_U_11
 _atom_site_aniso_U_22
 _atom_site_aniso_U_33
 _atom_site_aniso_U_23
 _atom_site_aniso_U_13
 _atom_site_aniso_U_12
Br 0.0625(3) 0.0622(3) 0.0501(2) -0.0218(2) -0.0002(2) 0.0183(3)
O1 0.0293(15) 0.0382(17) 0.0437(15) -0.0084(12) -0.0053(13) -0.0019(15)
O2 0.0374(17) 0.0481(18) 0.0629(19) -0.0244(18) 0.0075(14) 0.0006(18)
N1 0.0316(18) 0.0208(19) 0.0368(18) -0.0043(14) -0.0028(15) 0.0007(15)
C1 0.043(3) 0.033(2) 0.050(2) -0.0081(18) -0.013(2) -0.006(2)
C2 0.034(3) 0.023(2) 0.044(3) 0.0020(18) -0.004(2) -0.003(2)
C3 0.026(2) 0.024(2) 0.037(2) 0.0004(17) 0.0004(18) -0.0037(18)
C4 0.040(2) 0.024(2) 0.047(2) 0.0081(17) -0.009(2) 0.000(2)
C5 0.056(3) 0.055(3) 0.043(2) 0.011(2) -0.012(2) -0.013(3)
C6 0.030(2) 0.038(2) 0.048(2) -0.0046(19) 0.005(2) 0.000(2)
C7 0.024(2) 0.026(2) 0.033(2) -0.0026(17) -0.0017(17) -0.0032(18)
C8 0.031(2) 0.020(2) 0.0283(19) -0.0033(17) -0.0019(17) -0.0016(18)
C9 0.027(2) 0.024(2) 0.0297(19) -0.0036(15) -0.0039(17) -0.0025(17)
C10 0.037(2) 0.025(2) 0.035(2) 0.0003(18) -0.0043(18) 0.003(2)
C11 0.031(3) 0.040(3) 0.036(2) -0.004(2) 0.0042(19) -0.002(2)
C12 0.047(3) 0.034(3) 0.039(3) 0.0009(19) 0.003(2) -0.016(2)
C13 0.047(3) 0.024(2) 0.040(2) 0.0020(17) -0.002(2) -0.004(2)
C14 0.028(2) 0.027(2) 0.0291(19) -0.0013(18) -0.0034(16) -0.002(2)
C15 0.045(3) 0.025(2) 0.039(2) -0.0047(17) -0.004(2) 0.008(2)
C16 0.031(2) 0.029(2) 0.030(2) 0.0011(17) -0.0004(19) 0.0007(19)
C17 0.038(3) 0.029(2) 0.042(2) 0.0004(18) -0.0005(19) 0.005(2)
C18 0.036(2) 0.038(2) 0.048(2) 0.0010(19) -0.007(2) 0.003(2)
C19 0.043(2) 0.041(2) 0.031(2) -0.003(2) -0.0038(17) 0.000(2)
C20 0.038(3) 0.027(2) 0.034(2) -0.0006(16) 0.0081(18) 0.0028(18)
C21 0.0304(19) 0.0252(19) 0.0360(19) -0.0031(17) -0.0029(18) 0.000(2)
 
_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
Br C20 1.895(3) . ?
O1 C2 1.337(4) . ?
O1 C1 1.453(4) . ?
O2 C2 1.203(4) . ?
N1 C14 1.383(4) . ?
N1 C7 1.391(4) . ?
N1 C15 1.465(4) . ?
C2 C3 1.508(5) . ?
C3 C8 1.512(5) . ?
C3 C4 1.536(5) . ?
C4 C5 1.518(5) . ?
C6 C7 1.499(4) . ?
C7 C8 1.353(4) . ?
C8 C9 1.447(5) . ?
C9 C10 1.400(5) . ?
C9 C14 1.413(5) . ?
C10 C11 1.375(5) . ?
C11 C12 1.400(5) . ?
C12 C13 1.373(5) . ?
C13 C14 1.383(5) . ?
C15 C16 1.503(5) . ?
C16 C21 1.396(4) . ?
C16 C17 1.395(5) . ?
C17 C18 1.385(5) . ?
C18 C19 1.380(5) . ?
C19 C20 1.384(5) . ?
C20 C21 1.379(4) . ?
 
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
C2 O1 C1 116.5(3) . . ?
C14 N1 C7 108.8(3) . . ?
C14 N1 C15 125.5(3) . . ?
C7 N1 C15 125.0(3) . . ?
O2 C2 O1 122.6(4) . . ?
O2 C2 C3 126.8(4) . . ?
O1 C2 C3 110.6(3) . . ?
C8 C3 C2 110.9(3) . . ?
C8 C3 C4 111.8(3) . . ?
C2 C3 C4 112.2(3) . . ?
C5 C4 C3 111.5(3) . . ?
C8 C7 N1 109.9(3) . . ?
C8 C7 C6 130.5(3) . . ?
N1 C7 C6 119.6(3) . . ?
C7 C8 C9 107.0(3) . . ?
C7 C8 C3 126.3(3) . . ?
C9 C8 C3 126.5(3) . . ?
C10 C9 C14 118.0(3) . . ?
C10 C9 C8 135.1(3) . . ?
C14 C9 C8 106.9(3) . . ?
C11 C10 C9 119.4(4) . . ?
C10 C11 C12 121.1(4) . . ?
C13 C12 C11 121.1(4) . . ?
C12 C13 C14 117.6(4) . . ?
N1 C14 C13 129.9(4) . . ?
N1 C14 C9 107.3(3) . . ?
C13 C14 C9 122.8(3) . . ?
N1 C15 C16 113.1(3) . . ?
C21 C16 C17 118.2(3) . . ?
C21 C16 C15 119.4(3) . . ?
C17 C16 C15 122.4(3) . . ?
C18 C17 C16 120.5(4) . . ?
C17 C18 C19 121.4(4) . . ?
C20 C19 C18 117.9(3) . . ?
C19 C20 C21 121.7(3) . . ?
C19 C20 Br 118.6(3) . . ?
C21 C20 Br 119.6(3) . . ?
C20 C21 C16 120.3(3) . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
C1 O1 C2 O2 5.2(6) . . . . ?
C1 O1 C2 C3 -174.1(3) . . . . ?
O2 C2 C3 C8 -89.8(5) . . . . ?
O1 C2 C3 C8 89.5(4) . . . . ?
O2 C2 C3 C4 36.0(6) . . . . ?
O1 C2 C3 C4 -144.8(3) . . . . ?
C8 C3 C4 C5 -63.9(4) . . . . ?
C2 C3 C4 C5 170.8(3) . . . . ?
C14 N1 C7 C8 1.2(4) . . . . ?
C15 N1 C7 C8 171.5(3) . . . . ?
C14 N1 C7 C6 -179.5(3) . . . . ?
C15 N1 C7 C6 -9.2(5) . . . . ?
N1 C7 C8 C9 0.1(4) . . . . ?
C6 C7 C8 C9 -179.0(3) . . . . ?
N1 C7 C8 C3 -176.1(3) . . . . ?
C6 C7 C8 C3 4.7(6) . . . . ?
C2 C3 C8 C7 -119.0(4) . . . . ?
C4 C3 C8 C7 115.0(4) . . . . ?
C2 C3 C8 C9 65.5(5) . . . . ?
C4 C3 C8 C9 -60.5(5) . . . . ?
C7 C8 C9 C10 -179.3(4) . . . . ?
C3 C8 C9 C10 -3.0(6) . . . . ?
C7 C8 C9 C14 -1.3(4) . . . . ?
C3 C8 C9 C14 174.9(3) . . . . ?
C14 C9 C10 C11 -1.3(5) . . . . ?
C8 C9 C10 C11 176.5(4) . . . . ?
C9 C10 C11 C12 0.4(6) . . . . ?
C10 C11 C12 C13 0.1(6) . . . . ?
C11 C12 C13 C14 0.3(6) . . . . ?
C7 N1 C14 C13 176.5(4) . . . . ?
C15 N1 C14 C13 6.3(6) . . . . ?
C7 N1 C14 C9 -2.0(4) . . . . ?
C15 N1 C14 C9 -172.2(3) . . . . ?
C12 C13 C14 N1 -179.5(3) . . . . ?
C12 C13 C14 C9 -1.3(5) . . . . ?
C10 C9 C14 N1 -179.6(3) . . . . ?
C8 C9 C14 N1 2.0(4) . . . . ?
C10 C9 C14 C13 1.8(5) . . . . ?
C8 C9 C14 C13 -176.6(3) . . . . ?
C14 N1 C15 C16 93.9(4) . . . . ?
C7 N1 C15 C16 -74.8(4) . . . . ?
N1 C15 C16 C21 155.9(3) . . . . ?
N1 C15 C16 C17 -27.0(5) . . . . ?
C21 C16 C17 C18 -0.5(5) . . . . ?
C15 C16 C17 C18 -177.6(3) . . . . ?
C16 C17 C18 C19 0.8(6) . . . . ?
C17 C18 C19 C20 -0.7(6) . . . . ?
C18 C19 C20 C21 0.4(5) . . . . ?
C18 C19 C20 Br -178.8(3) . . . . ?
C19 C20 C21 C16 -0.1(5) . . . . ?
Br C20 C21 C16 179.1(3) . . . . ?
C17 C16 C21 C20 0.1(5) . . . . ?
C15 C16 C21 C20 177.3(3) . . . . ?
 
_diffrn_measured_fraction_theta_max    0.993
_diffrn_reflns_theta_full              25.00
_diffrn_measured_fraction_theta_full   0.999
_refine_diff_density_max    0.300
_refine_diff_density_min   -0.347
_refine_diff_density_rms    0.067