data_publication_text
_publ_contact_author_name        'Prof. H. V. R. Dias'
_publ_contact_author_address     
;Department of Chemistry and Biochemistry
The University of Texas at Arlington
Arlington, Texas 76019-0065, USA
;
_publ_contact_author_email       dias@uta.edu
_publ_contact_author_phone       817-272-3813
_publ_contact_author_fax         817-272-3808
loop_
_publ_author_name
_publ_author_address
'Prof. C. J. Lovely'
;Department of Chemistry and Biochemistry
The University of Texas at Arlington
Arlington, Texas 76019-0065, USA
;



data_dias530s

 

_audit_creation_method            SHELXL-97

_chemical_name_systematic

;

 ?

;

_chemical_name_common             C21H27N3O5=epi-(1).MeOH

_chemical_melting_point           ?

_chemical_formula_moiety          ?

_chemical_formula_sum

 'C21 H27 N3 O5'

_chemical_formula_weight          401.46

 

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'

 

_symmetry_cell_setting            Monoclinic

_symmetry_space_group_name_H-M    P2(1)/n

 

loop_

 _symmetry_equiv_pos_as_xyz

 'x, y, z'

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

 '-x, -y, -z'

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

 

_cell_length_a                    12.3916(6)

_cell_length_b                    8.4464(4)

_cell_length_c                    19.6714(10)

_cell_angle_alpha                 90.00

_cell_angle_beta                  101.228(1)

_cell_angle_gamma                 90.00

_cell_volume                      2019.49(17)

_cell_formula_units_Z             4

_cell_measurement_temperature     100(2)

_cell_measurement_reflns_used     6422

_cell_measurement_theta_min       2.63

_cell_measurement_theta_max       28.30

 

_exptl_crystal_description        rods

_exptl_crystal_colour             colorless

_exptl_crystal_size_max           0.36

_exptl_crystal_size_mid           0.15

_exptl_crystal_size_min           0.08

_exptl_crystal_density_meas       0

_exptl_crystal_density_diffrn     1.320

_exptl_crystal_density_method     'not measured'

_exptl_crystal_F_000              856

_exptl_absorpt_coefficient_mu     0.095

_exptl_absorpt_correction_type    multi-scan

_exptl_absorpt_correction_T_min   0.9665

_exptl_absorpt_correction_T_max   0.9929

_exptl_absorpt_process_details    sadabs

 

_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   'CCD area detector'

_diffrn_measurement_method        'phi and omega scans'

_diffrn_detector_area_resol_mean  ?

_diffrn_standards_number          ?

_diffrn_standards_interval_count  ?

_diffrn_standards_interval_time   ?

_diffrn_standards_decay_%         ?

_diffrn_reflns_number             16278

_diffrn_reflns_av_R_equivalents   0.0248

_diffrn_reflns_av_sigmaI/netI     0.0208

_diffrn_reflns_limit_h_min        -15

_diffrn_reflns_limit_h_max        15

_diffrn_reflns_limit_k_min        -10

_diffrn_reflns_limit_k_max        10

_diffrn_reflns_limit_l_min        -24

_diffrn_reflns_limit_l_max        24

_diffrn_reflns_theta_min          1.80

_diffrn_reflns_theta_max          26.00

_reflns_number_total              3969

_reflns_number_gt                 3426

_reflns_threshold_expression      >2sigma(I)

 

_computing_data_collection        'Bruker SMART'

_computing_cell_refinement        'Bruker SMART'

_computing_data_reduction         'Bruker SAINT'

_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics     'Bruker SHELXTL'

_computing_publication_material   'Bruker SHELXTL'

 

_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^)+(0.0790P)^2^+1.1123P] 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     mixed

_refine_ls_extinction_method      none

_refine_ls_extinction_coef        ?

_refine_ls_number_reflns          3969

_refine_ls_number_parameters      274

_refine_ls_number_restraints      0

_refine_ls_R_factor_all           0.0544

_refine_ls_R_factor_gt            0.0477

_refine_ls_wR_factor_ref          0.1372

_refine_ls_wR_factor_gt           0.1291

_refine_ls_goodness_of_fit_ref    1.043

_refine_ls_restrained_S_all       1.043

_refine_ls_shift/su_max           0.000

_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

N1 N 0.57547(11) 1.07127(16) 0.32847(7) 0.0200(3) Uani 1 1 d . . .

N2 N 0.54957(11) 0.83794(16) 0.37516(7) 0.0204(3) Uani 1 1 d . . .

N3 N 0.45355(11) 1.06264(17) 0.40588(7) 0.0233(3) Uani 1 1 d . . .

H3A H 0.4200 1.0092 0.4341 0.028 Uiso 1 1 calc R . .

H3B H 0.4416 1.1648 0.3998 0.028 Uiso 1 1 calc R . .

O1 O 0.69287(9) 1.00318(14) 0.25543(6) 0.0241(3) Uani 1 1 d . . .

O2 O 0.72798(9) 0.61131(14) 0.40210(6) 0.0251(3) Uani 1 1 d . . .

O3 O 0.91696(10) 1.23509(14) 0.56653(6) 0.0282(3) Uani 1 1 d . . .

O4 O 0.15523(10) 0.82746(16) 0.12134(7) 0.0270(3) Uani 1 1 d . . .

O5 O 0.09744(12) 0.12865(17) 0.07811(7) 0.0364(3) Uani 1 1 d . . .

C1 C 0.51973(12) 0.99163(19) 0.37356(8) 0.0191(3) Uani 1 1 d . . .

C2 C 0.63772(12) 0.96922(19) 0.29817(8) 0.0199(3) Uani 1 1 d . . .

C3 C 0.62679(13) 0.80622(19) 0.32942(8) 0.0204(3) Uani 1 1 d . . .

C4 C 0.57545(15) 1.24189(19) 0.31884(9) 0.0257(4) Uani 1 1 d . . .

H4A H 0.6284 1.2700 0.2898 0.039 Uiso 1 1 calc R . .

H4B H 0.5962 1.2939 0.3640 0.039 Uiso 1 1 calc R . .

H4C H 0.5017 1.2767 0.2963 0.039 Uiso 1 1 calc R . .

C5 C 0.58351(14) 0.6823(2) 0.27329(9) 0.0242(4) Uani 1 1 d . . .

H5A H 0.6349 0.6759 0.2407 0.029 Uiso 1 1 calc R . .

H5B H 0.5824 0.5774 0.2956 0.029 Uiso 1 1 calc R . .

C6 C 0.46956(13) 0.71871(19) 0.23286(8) 0.0220(3) Uani 1 1 d . . .

C7 C 0.37691(14) 0.6441(2) 0.24822(8) 0.0232(4) Uani 1 1 d . . .

H7 H 0.3859 0.5675 0.2842 0.028 Uiso 1 1 calc R . .

C8 C 0.27187(14) 0.6791(2) 0.21223(8) 0.0238(4) Uani 1 1 d . . .

H8 H 0.2099 0.6272 0.2239 0.029 Uiso 1 1 calc R . .

C9 C 0.25727(13) 0.7904(2) 0.15902(8) 0.0223(4) Uani 1 1 d . . .

C10 C 0.34863(14) 0.8657(2) 0.14263(9) 0.0250(4) Uani 1 1 d . . .

H10 H 0.3395 0.9418 0.1064 0.030 Uiso 1 1 calc R . .

C11 C 0.45284(14) 0.8298(2) 0.17919(8) 0.0247(4) Uani 1 1 d . . .

H11 H 0.5146 0.8820 0.1675 0.030 Uiso 1 1 calc R . .

C12 C 0.74207(13) 0.75957(19) 0.37120(8) 0.0205(3) Uani 1 1 d . . .

H12 H 0.7934 0.7457 0.3382 0.025 Uiso 1 1 calc R . .

C13 C 0.78919(13) 0.88390(19) 0.42448(8) 0.0207(3) Uani 1 1 d . . .

C14 C 0.76284(13) 0.8837(2) 0.48996(9) 0.0228(4) Uani 1 1 d . . .

H14 H 0.7157 0.8037 0.5015 0.027 Uiso 1 1 calc R . .

C15 C 0.80408(14) 0.9983(2) 0.53891(9) 0.0237(4) Uani 1 1 d . . .

H15 H 0.7858 0.9956 0.5836 0.028 Uiso 1 1 calc R . .

C16 C 0.87229(13) 1.11714(19) 0.52209(9) 0.0228(4) Uani 1 1 d . . .

C17 C 0.89995(13) 1.1187(2) 0.45662(9) 0.0233(4) Uani 1 1 d . . .

H17 H 0.9467 1.1991 0.4449 0.028 Uiso 1 1 calc R . .

C18 C 0.85917(13) 1.00294(19) 0.40884(8) 0.0219(4) Uani 1 1 d . . .

H18 H 0.8790 1.0041 0.3646 0.026 Uiso 1 1 calc R . .

C19 C 0.83065(15) 0.5350(2) 0.42719(10) 0.0322(4) Uani 1 1 d . . .

H19A H 0.8694 0.5192 0.3888 0.048 Uiso 1 1 calc R . .

H19B H 0.8175 0.4321 0.4472 0.048 Uiso 1 1 calc R . .

H19C H 0.8755 0.6011 0.4628 0.048 Uiso 1 1 calc R . .

C20 C 0.90228(17) 1.2226(2) 0.63648(9) 0.0342(4) Uani 1 1 d . . .

H20A H 0.8240 1.2339 0.6379 0.051 Uiso 1 1 calc R . .

H20B H 0.9442 1.3063 0.6644 0.051 Uiso 1 1 calc R . .

H20C H 0.9285 1.1190 0.6552 0.051 Uiso 1 1 calc R . .

C21 C 0.11222(17) 0.1404(2) 0.00950(10) 0.0352(4) Uani 1 1 d . . .

H21A H 0.0573 0.2131 -0.0162 0.053 Uiso 1 1 calc R . .

H21B H 0.1035 0.0357 -0.0123 0.053 Uiso 1 1 calc R . .

H21C H 0.1862 0.1808 0.0090 0.053 Uiso 1 1 calc R . .

H5D H 0.111(2) 0.030(3) 0.0916(13) 0.052(7) Uiso 1 1 d . . .

H4D H 0.125(2) 0.748(4) 0.1168(14) 0.057(8) Uiso 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

N1 0.0209(7) 0.0176(7) 0.0218(7) 0.0013(5) 0.0045(5) 0.0007(5)

N2 0.0194(7) 0.0189(7) 0.0236(7) -0.0001(5) 0.0061(5) 0.0017(5)

N3 0.0243(7) 0.0197(7) 0.0275(7) 0.0014(6) 0.0089(6) 0.0030(6)

O1 0.0235(6) 0.0273(6) 0.0226(6) 0.0016(5) 0.0072(5) -0.0018(5)

O2 0.0250(6) 0.0190(6) 0.0312(6) 0.0039(5) 0.0055(5) 0.0031(5)

O3 0.0321(7) 0.0232(6) 0.0281(6) -0.0015(5) 0.0024(5) -0.0015(5)

O4 0.0250(6) 0.0207(6) 0.0326(7) 0.0021(5) -0.0007(5) -0.0022(5)

O5 0.0492(9) 0.0302(7) 0.0336(7) 0.0065(6) 0.0173(6) 0.0161(6)

C1 0.0170(7) 0.0197(8) 0.0194(7) 0.0000(6) 0.0006(6) -0.0016(6)

C2 0.0170(7) 0.0219(8) 0.0197(8) -0.0011(6) 0.0010(6) -0.0011(6)

C3 0.0193(8) 0.0202(8) 0.0231(8) 0.0006(6) 0.0072(6) 0.0013(6)

C4 0.0328(9) 0.0178(8) 0.0275(9) 0.0021(7) 0.0085(7) -0.0002(7)

C5 0.0247(8) 0.0206(8) 0.0276(8) -0.0030(7) 0.0060(7) 0.0012(7)

C6 0.0243(8) 0.0188(8) 0.0232(8) -0.0045(6) 0.0050(6) -0.0009(6)

C7 0.0278(9) 0.0202(8) 0.0214(8) 0.0004(6) 0.0043(6) -0.0013(7)

C8 0.0237(8) 0.0229(8) 0.0258(8) -0.0004(7) 0.0072(7) -0.0044(7)

C9 0.0232(8) 0.0200(8) 0.0231(8) -0.0032(6) 0.0029(6) 0.0000(6)

C10 0.0305(9) 0.0214(8) 0.0224(8) 0.0021(6) 0.0037(7) -0.0038(7)

C11 0.0238(8) 0.0264(9) 0.0246(8) -0.0026(7) 0.0067(7) -0.0066(7)

C12 0.0198(8) 0.0196(8) 0.0234(8) 0.0026(6) 0.0070(6) 0.0026(6)

C13 0.0168(7) 0.0204(8) 0.0244(8) 0.0034(6) 0.0029(6) 0.0044(6)

C14 0.0197(8) 0.0215(8) 0.0276(8) 0.0030(6) 0.0055(6) 0.0007(6)

C15 0.0236(8) 0.0256(9) 0.0228(8) 0.0021(6) 0.0066(6) 0.0033(7)

C16 0.0204(8) 0.0187(8) 0.0275(9) 0.0009(6) 0.0003(6) 0.0036(6)

C17 0.0189(8) 0.0210(8) 0.0294(9) 0.0065(7) 0.0035(6) 0.0009(6)

C18 0.0182(8) 0.0245(8) 0.0235(8) 0.0050(6) 0.0049(6) 0.0044(6)

C19 0.0327(10) 0.0275(9) 0.0375(10) 0.0070(8) 0.0097(8) 0.0126(8)

C20 0.0451(11) 0.0265(10) 0.0285(9) -0.0032(7) 0.0009(8) 0.0010(8)

C21 0.0415(11) 0.0332(10) 0.0321(10) 0.0003(8) 0.0102(8) -0.0033(8)

 

_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

N1 C2 1.368(2) . ?

N1 C1 1.398(2) . ?

N1 C4 1.453(2) . ?

N2 C1 1.348(2) . ?

N2 C3 1.460(2) . ?

N3 C1 1.280(2) . ?

N3 H3A 0.8800 . ?

N3 H3B 0.8800 . ?

O1 C2 1.2165(19) . ?

O2 C12 1.4176(19) . ?

O2 C19 1.426(2) . ?

O3 C16 1.369(2) . ?

O3 C20 1.427(2) . ?

O4 C9 1.372(2) . ?

O4 H4D 0.76(3) . ?

O5 C21 1.400(2) . ?

O5 H5D 0.88(3) . ?

C2 C3 1.525(2) . ?

C3 C5 1.540(2) . ?

C3 C12 1.554(2) . ?

C4 H4A 0.9800 . ?

C4 H4B 0.9800 . ?

C4 H4C 0.9800 . ?

C5 C6 1.511(2) . ?

C5 H5A 0.9900 . ?

C5 H5B 0.9900 . ?

C6 C7 1.393(2) . ?

C6 C11 1.397(2) . ?

C7 C8 1.387(2) . ?

C7 H7 0.9500 . ?

C8 C9 1.392(2) . ?

C8 H8 0.9500 . ?

C9 C10 1.390(2) . ?

C10 C11 1.384(2) . ?

C10 H10 0.9500 . ?

C11 H11 0.9500 . ?

C12 C13 1.518(2) . ?

C12 H12 1.0000 . ?

C13 C14 1.389(2) . ?

C13 C18 1.401(2) . ?

C14 C15 1.390(2) . ?

C14 H14 0.9500 . ?

C15 C16 1.393(2) . ?

C15 H15 0.9500 . ?

C16 C17 1.396(2) . ?

C17 C18 1.382(2) . ?

C17 H17 0.9500 . ?

C18 H18 0.9500 . ?

C19 H19A 0.9800 . ?

C19 H19B 0.9800 . ?

C19 H19C 0.9800 . ?

C20 H20A 0.9800 . ?

C20 H20B 0.9800 . ?

C20 H20C 0.9800 . ?

C21 H21A 0.9800 . ?

C21 H21B 0.9800 . ?

C21 H21C 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

C2 N1 C1 111.30(13) . . ?

C2 N1 C4 123.62(14) . . ?

C1 N1 C4 124.89(13) . . ?

C1 N2 C3 111.83(13) . . ?

C1 N3 H3A 120.0 . . ?

C1 N3 H3B 120.0 . . ?

H3A N3 H3B 120.0 . . ?

C12 O2 C19 111.82(13) . . ?

C16 O3 C20 116.77(14) . . ?

C9 O4 H4D 104(2) . . ?

C21 O5 H5D 107.9(16) . . ?

N3 C1 N2 129.69(15) . . ?

N3 C1 N1 122.20(15) . . ?

N2 C1 N1 108.11(13) . . ?

O1 C2 N1 126.35(15) . . ?

O1 C2 C3 126.69(14) . . ?

N1 C2 C3 106.94(13) . . ?

N2 C3 C2 101.72(12) . . ?

N2 C3 C5 112.83(13) . . ?

C2 C3 C5 111.75(13) . . ?

N2 C3 C12 111.46(13) . . ?

C2 C3 C12 107.32(12) . . ?

C5 C3 C12 111.28(13) . . ?

N1 C4 H4A 109.5 . . ?

N1 C4 H4B 109.5 . . ?

H4A C4 H4B 109.5 . . ?

N1 C4 H4C 109.5 . . ?

H4A C4 H4C 109.5 . . ?

H4B C4 H4C 109.5 . . ?

C6 C5 C3 113.47(13) . . ?

C6 C5 H5A 108.9 . . ?

C3 C5 H5A 108.9 . . ?

C6 C5 H5B 108.9 . . ?

C3 C5 H5B 108.9 . . ?

H5A C5 H5B 107.7 . . ?

C7 C6 C11 117.39(15) . . ?

C7 C6 C5 121.25(15) . . ?

C11 C6 C5 121.35(15) . . ?

C8 C7 C6 121.61(15) . . ?

C8 C7 H7 119.2 . . ?

C6 C7 H7 119.2 . . ?

C7 C8 C9 119.95(15) . . ?

C7 C8 H8 120.0 . . ?

C9 C8 H8 120.0 . . ?

O4 C9 C10 118.46(15) . . ?

O4 C9 C8 122.13(15) . . ?

C10 C9 C8 119.41(15) . . ?

C11 C10 C9 119.91(16) . . ?

C11 C10 H10 120.0 . . ?

C9 C10 H10 120.0 . . ?

C10 C11 C6 121.73(15) . . ?

C10 C11 H11 119.1 . . ?

C6 C11 H11 119.1 . . ?

O2 C12 C13 112.20(13) . . ?

O2 C12 C3 105.87(12) . . ?

C13 C12 C3 112.35(13) . . ?

O2 C12 H12 108.8 . . ?

C13 C12 H12 108.8 . . ?

C3 C12 H12 108.8 . . ?

C14 C13 C18 118.15(15) . . ?

C14 C13 C12 120.76(14) . . ?

C18 C13 C12 121.08(14) . . ?

C13 C14 C15 121.36(15) . . ?

C13 C14 H14 119.3 . . ?

C15 C14 H14 119.3 . . ?

C14 C15 C16 119.68(15) . . ?

C14 C15 H15 120.2 . . ?

C16 C15 H15 120.2 . . ?

O3 C16 C15 124.14(15) . . ?

O3 C16 C17 116.17(15) . . ?

C15 C16 C17 119.69(15) . . ?

C18 C17 C16 119.87(15) . . ?

C18 C17 H17 120.1 . . ?

C16 C17 H17 120.1 . . ?

C17 C18 C13 121.23(15) . . ?

C17 C18 H18 119.4 . . ?

C13 C18 H18 119.4 . . ?

O2 C19 H19A 109.5 . . ?

O2 C19 H19B 109.5 . . ?

H19A C19 H19B 109.5 . . ?

O2 C19 H19C 109.5 . . ?

H19A C19 H19C 109.5 . . ?

H19B C19 H19C 109.5 . . ?

O3 C20 H20A 109.5 . . ?

O3 C20 H20B 109.5 . . ?

H20A C20 H20B 109.5 . . ?

O3 C20 H20C 109.5 . . ?

H20A C20 H20C 109.5 . . ?

H20B C20 H20C 109.5 . . ?

O5 C21 H21A 109.5 . . ?

O5 C21 H21B 109.5 . . ?

H21A C21 H21B 109.5 . . ?

O5 C21 H21C 109.5 . . ?

H21A C21 H21C 109.5 . . ?

H21B C21 H21C 109.5 . . ?

 

_diffrn_measured_fraction_theta_max    1.000

_diffrn_reflns_theta_full              26.00

_diffrn_measured_fraction_theta_full   1.000

_refine_diff_density_max    0.777

_refine_diff_density_min   -0.600

_refine_diff_density_rms    0.057