data_flv02

 

_audit_creation_method            SHELXL-97

_chemical_name_systematic

;

 ?

;

_chemical_name_common             ?

_chemical_melting_point           ?

_chemical_formula_moiety          
 'C22 H19 Br N2 O5'

_chemical_formula_sum

 'C22 H19 Br N2 O5'

_chemical_formula_weight          471.30

 

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+1/2, -y+1/2, -z'

 '-x, y+1/2, -z+1/2'

 

_cell_length_a                    9.1581(2)

_cell_length_b                    12.6857(3)

_cell_length_c                    16.7030(3)

_cell_angle_alpha                 90.00

_cell_angle_beta                  90.00

_cell_angle_gamma                 90.00

_cell_volume                      1940.50(7)

_cell_formula_units_Z             4

_cell_measurement_temperature     100(2)

_cell_measurement_reflns_used     9803

_cell_measurement_theta_min       2.44

_cell_measurement_theta_max       37.44

 

_exptl_crystal_description        Block

_exptl_crystal_colour             'Light yellow'

_exptl_crystal_size_max           0.25

_exptl_crystal_size_mid           0.25

_exptl_crystal_size_min           0.22

_exptl_crystal_density_meas       .

_exptl_crystal_density_diffrn     1.613

_exptl_crystal_density_method     'not measured'

_exptl_crystal_F_000              960

_exptl_absorpt_coefficient_mu     2.157

_exptl_absorpt_correction_type    none

_exptl_absorpt_correction_T_min   0.6146

_exptl_absorpt_correction_T_max   0.6482

_exptl_absorpt_process_details    ?

 

_exptl_special_details

;

 ?

;

 

_diffrn_ambient_temperature       100(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 SMART 1000'

_diffrn_measurement_method        '\w scans at 9 \f settings'

_diffrn_detector_area_resol_mean  ?

_diffrn_reflns_number             61657

_diffrn_reflns_av_R_equivalents   0.0854

_diffrn_reflns_av_sigmaI/netI     0.0518

_diffrn_reflns_limit_h_min        -15

_diffrn_reflns_limit_h_max        15

_diffrn_reflns_limit_k_min        -22

_diffrn_reflns_limit_k_max        22

_diffrn_reflns_limit_l_min        -29

_diffrn_reflns_limit_l_max        29

_diffrn_reflns_theta_min          2.02

_diffrn_reflns_theta_max          38.73

_reflns_number_total              10781

_reflns_number_gt                 9216

_reflns_threshold_expression      >2sigma(I)

 

_computing_data_collection        'Bruker SMART v5.630'

_computing_cell_refinement        'Bruker SAINT v6.45A'

_computing_data_reduction         'Bruker SAINT v6.45A'

_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'

_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)'

_computing_molecular_graphics     'Bruker XP v5.1'

_computing_publication_material   'Bruker XCIF v6.12'

 

_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 matrix' 
_refine_ls_weighting_scheme       Sigma
_refine_ls_weighting_details      'w=1/s^2^(Fo^2^)' 
_atom_sites_solution_primary      'Direct methods'
_atom_sites_solution_secondary    'Difference Fourier map'
_atom_sites_solution_hydrogens    'Geometric positions'
_refine_ls_hydrogen_treatment     Riding 
_chemical_absolute_configuration  ad
_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    -0.009(3)

_refine_ls_number_reflns          10781

_refine_ls_number_parameters      272

_refine_ls_number_restraints      0

_refine_ls_R_factor_all           0.0337

_refine_ls_R_factor_gt            0.0252

_refine_ls_wR_factor_ref          0.0500

_refine_ls_wR_factor_gt           0.0489

_refine_ls_goodness_of_fit_ref    1.035

_refine_ls_restrained_S_all       1.035

_refine_ls_shift/su_max           0.002

_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 0.617214(11) 0.824013(8) 0.816666(6) 0.01454(2) Uani 1 1 d . . .

O1 O 0.39066(9) 0.96719(6) 0.49851(4) 0.01664(14) Uani 1 1 d . . .

O2 O 0.69183(8) 0.83492(6) 0.50244(4) 0.01452(14) Uani 1 1 d . . .

O3 O 0.87388(9) 0.94338(5) 0.51907(4) 0.01391(13) Uani 1 1 d . . .

O4 O 0.86252(8) 0.77369(6) 0.63942(5) 0.01541(15) Uani 1 1 d . . .

O5 O 1.08094(8) 0.83986(6) 0.64523(5) 0.01906(16) Uani 1 1 d . . .

N1 N 0.30933(9) 1.04084(7) 0.61529(5) 0.01204(15) Uani 1 1 d . . .

N2 N 0.94898(9) 0.84309(6) 0.65872(5) 0.01220(15) Uani 1 1 d . . .

C1 C 0.48510(11) 0.93342(8) 0.78818(6) 0.01064(16) Uani 1 1 d . . .

C2 C 0.41500(11) 0.98357(8) 0.85188(6) 0.01303(18) Uani 1 1 d . . .

H2 H 0.4409 0.9667 0.9054 0.016 Uiso 1 1 calc R . .

C3 C 0.30742(12) 1.05818(8) 0.83693(6) 0.01306(18) Uani 1 1 d . . .

H3 H 0.2617 1.0933 0.8804 0.016 Uiso 1 1 calc R . .

C4 C 0.26598(11) 1.08196(8) 0.75883(6) 0.01252(18) Uani 1 1 d . . .

H4 H 0.1901 1.1310 0.7482 0.015 Uiso 1 1 calc R . .

C5 C 0.33929(10) 1.03161(7) 0.69718(5) 0.00998(16) Uani 1 1 d . . .

C6 C 0.45528(10) 0.96050(7) 0.70915(6) 0.00944(16) Uani 1 1 d . . .

C7 C 0.51577(10) 0.92885(7) 0.62756(6) 0.00996(16) Uani 1 1 d . . .

C8 C 0.39975(11) 0.97863(8) 0.57097(6) 0.01204(17) Uani 1 1 d . . .

C9 C 0.18252(11) 1.09501(9) 0.58266(7) 0.01624(19) Uani 1 1 d . . .

H9A H 0.1843 1.0905 0.5241 0.024 Uiso 1 1 calc R . .

H9B H 0.1846 1.1692 0.5990 0.024 Uiso 1 1 calc R . .

H9C H 0.0933 1.0618 0.6029 0.024 Uiso 1 1 calc R . .

C10 C 0.51995(11) 0.80872(7) 0.61523(6) 0.01247(18) Uani 1 1 d . . .

H10A H 0.5908 0.7774 0.6531 0.015 Uiso 1 1 calc R . .

H10B H 0.4225 0.7789 0.6274 0.015 Uiso 1 1 calc R . .

C11 C 0.56257(12) 0.77896(8) 0.53056(6) 0.01459(18) Uani 1 1 d . . .

H11A H 0.5813 0.7022 0.5283 0.018 Uiso 1 1 calc R . .

H11B H 0.4799 0.7945 0.4942 0.018 Uiso 1 1 calc R . .

C12 C 0.75351(11) 0.91519(7) 0.54077(6) 0.01056(16) Uani 1 1 d . . .

C13 C 0.67340(10) 0.97828(7) 0.60666(5) 0.00883(15) Uani 1 1 d . . .

C14 C 0.65231(11) 1.09149(8) 0.56770(6) 0.01228(18) Uani 1 1 d . . .

H14A H 0.6064 1.0821 0.5145 0.015 Uiso 1 1 calc R . .

H14B H 0.5827 1.1316 0.6013 0.015 Uiso 1 1 calc R . .

C15 C 0.78756(12) 1.15767(8) 0.55704(6) 0.01436(19) Uani 1 1 d . . .

H15 H 0.8634 1.1308 0.5240 0.017 Uiso 1 1 calc R . .

C16 C 0.80704(14) 1.25075(9) 0.59083(8) 0.0224(2) Uani 1 1 d . . .

H16A H 0.7332 1.2797 0.6242 0.027 Uiso 1 1 calc R . .

H16B H 0.8949 1.2887 0.5818 0.027 Uiso 1 1 calc R . .

C17 C 0.76852(10) 0.99122(7) 0.68230(6) 0.00915(14) Uani 1 1 d . . .

C18 C 0.73176(11) 1.07310(8) 0.73523(6) 0.01195(17) Uani 1 1 d . . .

H18 H 0.6526 1.1181 0.7217 0.014 Uiso 1 1 calc R . .

C19 C 0.80563(12) 1.09123(8) 0.80635(6) 0.01515(19) Uani 1 1 d . . .

H19 H 0.7740 1.1458 0.8412 0.018 Uiso 1 1 calc R . .

C20 C 0.92537(12) 1.03020(9) 0.82693(6) 0.0171(2) Uani 1 1 d . . .

H20 H 0.9754 1.0417 0.8760 0.020 Uiso 1 1 calc R . .

C21 C 0.97068(11) 0.95213(8) 0.77469(6) 0.01422(18) Uani 1 1 d . . .

H21 H 1.0549 0.9113 0.7866 0.017 Uiso 1 1 calc R . .

C22 C 0.89249(11) 0.93343(7) 0.70454(5) 0.01054(15) Uani 1 1 d . . .

 

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

Br1 0.01633(4) 0.01674(4) 0.01053(4) 0.00410(4) 0.00084(4) 0.00327(4)

O1 0.0154(3) 0.0265(4) 0.0081(3) -0.0009(3) -0.0027(3) -0.0009(3)

O2 0.0166(3) 0.0173(3) 0.0096(3) -0.0045(3) 0.0020(3) -0.0031(3)

O3 0.0132(3) 0.0170(3) 0.0115(3) 0.0006(2) 0.0034(3) 0.0001(3)

O4 0.0182(4) 0.0119(3) 0.0161(3) -0.0008(2) 0.0007(3) -0.0030(3)

O5 0.0111(3) 0.0226(4) 0.0235(4) -0.0021(3) 0.0009(3) 0.0043(3)

N1 0.0092(4) 0.0177(4) 0.0092(3) 0.0020(3) -0.0010(3) -0.0001(3)

N2 0.0135(4) 0.0122(4) 0.0108(3) 0.0024(3) -0.0005(3) 0.0014(3)

C1 0.0099(4) 0.0128(4) 0.0092(4) 0.0007(3) 0.0000(3) -0.0008(3)

C2 0.0148(5) 0.0155(4) 0.0088(4) -0.0003(3) 0.0029(3) -0.0019(3)

C3 0.0145(4) 0.0134(4) 0.0113(4) -0.0020(3) 0.0041(3) -0.0017(3)

C4 0.0115(4) 0.0120(4) 0.0141(4) -0.0001(3) 0.0028(4) -0.0002(3)

C5 0.0096(4) 0.0118(4) 0.0085(4) 0.0012(3) 0.0010(3) -0.0020(3)

C6 0.0094(4) 0.0120(4) 0.0070(3) 0.0001(3) 0.0008(3) -0.0015(3)

C7 0.0092(4) 0.0138(4) 0.0069(4) -0.0013(3) 0.0002(3) -0.0007(3)

C8 0.0096(4) 0.0164(4) 0.0102(4) 0.0007(3) -0.0010(3) -0.0031(3)

C9 0.0113(5) 0.0217(5) 0.0157(5) 0.0036(4) -0.0033(4) 0.0013(4)

C10 0.0130(4) 0.0137(4) 0.0107(4) -0.0016(3) 0.0013(3) -0.0034(3)

C11 0.0160(5) 0.0158(4) 0.0120(4) -0.0043(3) 0.0004(4) -0.0041(4)

C12 0.0137(4) 0.0119(4) 0.0060(4) 0.0002(3) -0.0003(3) 0.0007(3)

C13 0.0091(4) 0.0105(4) 0.0070(4) -0.0003(3) -0.0002(3) -0.0001(3)

C14 0.0113(4) 0.0134(4) 0.0122(4) 0.0026(3) -0.0008(3) 0.0005(3)

C15 0.0130(4) 0.0142(5) 0.0158(4) 0.0045(3) 0.0001(3) 0.0000(3)

C16 0.0203(6) 0.0169(5) 0.0299(6) 0.0019(4) 0.0021(5) -0.0023(4)

C17 0.0091(4) 0.0109(3) 0.0075(3) -0.0001(3) 0.0002(3) -0.0017(3)

C18 0.0116(4) 0.0137(4) 0.0106(4) -0.0016(3) 0.0009(3) -0.0009(3)

C19 0.0159(4) 0.0181(4) 0.0114(5) -0.0054(3) 0.0006(4) -0.0037(4)

C20 0.0147(4) 0.0262(5) 0.0103(5) -0.0028(4) -0.0031(3) -0.0048(4)

C21 0.0114(4) 0.0189(5) 0.0124(4) 0.0021(3) -0.0030(3) -0.0010(4)

C22 0.0104(4) 0.0119(4) 0.0093(3) 0.0004(3) 0.0002(3) -0.0003(3)

 

_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

Br1 C1 1.9017(10) . ?

O1 C8 1.2218(12) . ?

O2 C12 1.3289(12) . ?

O2 C11 1.4580(13) . ?

O3 C12 1.2142(12) . ?

O4 N2 1.2271(11) . ?

O5 N2 1.2300(11) . ?

N1 C8 1.3625(13) . ?

N1 C5 1.3999(12) . ?

N1 C9 1.4553(13) . ?

N2 C22 1.4720(12) . ?

C1 C6 1.3911(14) . ?

C1 C2 1.3962(14) . ?

C2 C3 1.3888(15) . ?

C3 C4 1.3917(15) . ?

C4 C5 1.3854(14) . ?

C5 C6 1.4079(14) . ?

C6 C7 1.5248(13) . ?

C7 C10 1.5383(13) . ?

C7 C8 1.5561(14) . ?

C7 C13 1.6122(13) . ?

C10 C11 1.5149(14) . ?

C12 C13 1.5460(13) . ?

C13 C17 1.5433(13) . ?

C13 C14 1.5885(13) . ?

C14 C15 1.5070(14) . ?

C15 C16 1.3208(15) . ?

C17 C22 1.4016(14) . ?

C17 C18 1.4049(14) . ?

C18 C19 1.3862(14) . ?

C19 C20 1.3857(16) . ?

C20 C21 1.3836(15) . ?

C21 C22 1.3936(14) . ?

 

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

C12 O2 C11 124.26(8) . . ?

C8 N1 C5 111.30(8) . . ?

C8 N1 C9 123.71(8) . . ?

C5 N1 C9 124.18(9) . . ?

O4 N2 O5 124.19(9) . . ?

O4 N2 C22 117.92(8) . . ?

O5 N2 C22 117.81(8) . . ?

C6 C1 C2 121.36(9) . . ?

C6 C1 Br1 122.86(7) . . ?

C2 C1 Br1 115.75(7) . . ?

C3 C2 C1 119.98(9) . . ?

C2 C3 C4 120.64(9) . . ?

C5 C4 C3 117.69(9) . . ?

C4 C5 N1 126.35(9) . . ?

C4 C5 C6 123.75(9) . . ?

N1 C5 C6 109.89(8) . . ?

C1 C6 C5 116.17(9) . . ?

C1 C6 C7 135.37(9) . . ?

C5 C6 C7 108.42(8) . . ?

C6 C7 C10 112.93(8) . . ?

C6 C7 C8 100.84(7) . . ?

C10 C7 C8 109.74(8) . . ?

C6 C7 C13 114.61(8) . . ?

C10 C7 C13 109.51(8) . . ?

C8 C7 C13 108.78(7) . . ?

O1 C8 N1 124.44(9) . . ?

O1 C8 C7 126.88(9) . . ?

N1 C8 C7 108.66(8) . . ?

C11 C10 C7 112.23(8) . . ?

O2 C11 C10 112.87(8) . . ?

O3 C12 O2 117.89(9) . . ?

O3 C12 C13 119.40(8) . . ?

O2 C12 C13 122.54(8) . . ?

C17 C13 C12 111.72(8) . . ?

C17 C13 C14 107.93(7) . . ?

C12 C13 C14 103.53(7) . . ?

C17 C13 C7 111.69(7) . . ?

C12 C13 C7 112.19(7) . . ?

C14 C13 C7 109.36(7) . . ?

C15 C14 C13 116.88(8) . . ?

C16 C15 C14 123.95(11) . . ?

C22 C17 C18 114.45(9) . . ?

C22 C17 C13 128.21(8) . . ?

C18 C17 C13 117.30(8) . . ?

C19 C18 C17 123.03(10) . . ?

C20 C19 C18 120.40(10) . . ?

C21 C20 C19 118.74(10) . . ?

C20 C21 C22 119.86(10) . . ?

C21 C22 C17 123.37(9) . . ?

C21 C22 N2 112.90(9) . . ?

C17 C22 N2 123.65(8) . . ?

 

_diffrn_measured_fraction_theta_max    0.980

_diffrn_reflns_theta_full              38.73

_diffrn_measured_fraction_theta_full   0.980

_refine_diff_density_max    0.506

_refine_diff_density_min   -0.302

_refine_diff_density_rms    0.071