# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2008

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Jonathan Parr'
_publ_contact_author_email       JONATHAN.PARR@YALE.EDU

_publ_section_title              
;
Structural studies of C-ring substituted unnatural
analogues of prodigiosin
;
loop_
_publ_author_name
'Jonathan Parr'
'Christopher D Incarvito'
'Samir Jenkins'
'Harry H Wasserman'

# Attachment 'parr_sj01_b'

data_sj01
_database_code_depnum_ccdc_archive 'CCDC 696084'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H18 Cl N3 O'
_chemical_formula_weight         303.78

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'
Cl Cl 0.1484 0.1585 '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)/c

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

_cell_length_a                   9.751(2)
_cell_length_b                   9.5910(19)
_cell_length_c                   16.301(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.27(3)
_cell_angle_gamma                90.00
_cell_volume                     1512.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9390
_exptl_absorpt_correction_T_max  0.9874
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(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  'Nonius KappaCCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5864
_diffrn_reflns_av_R_equivalents  0.1592
_diffrn_reflns_av_sigmaI/netI    0.2347
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.11
_diffrn_reflns_theta_max         26.99
_reflns_number_total             3298
_reflns_number_gt                1314
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Nonius Collect'
_computing_cell_refinement       Denzo
_computing_data_reduction        Denzo
_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 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. The methyl H-atom coordinates
were derived using HFIX 33 which may mean that they are not completely reliable.
;

_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)+(0.1000P)²+0.0000P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3298
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2360
_refine_ls_R_factor_gt           0.0846
_refine_ls_wR_factor_ref         0.2297
_refine_ls_wR_factor_gt          0.1663
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_restrained_S_all      0.959
_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
Cl1 Cl 0.80382(15) 0.10497(16) 0.20465(8) 0.0364(5) Uani 1 1 d . . .
O1 O 0.7359(4) -0.0537(4) -0.1952(2) 0.0333(10) Uani 1 1 d . . .
N1 N 0.9992(5) 0.2711(5) 0.0992(3) 0.0336(12) Uani 1 1 d . . .
H1 H 0.949(6) 0.214(6) 0.137(3) 0.046(18) Uiso 1 1 d . . .
N2 N 0.8125(4) 0.0652(4) 0.0094(3) 0.0254(11) Uani 1 1 d . . .
H2 H 0.801(6) 0.068(6) 0.065(4) 0.047(19) Uiso 1 1 d . . .
N3 N 0.6067(5) -0.1224(5) 0.1101(3) 0.0274(11) Uani 1 1 d . . .
H3 H 0.662(7) -0.058(8) 0.126(4) 0.07(3) Uiso 1 1 d . . .
C1 C 1.0968(6) 0.3704(6) 0.1205(4) 0.0399(16) Uani 1 1 d . . .
H1A H 1.1214 0.4080 0.1743 0.048 Uiso 1 1 calc R . .
C2 C 1.1538(6) 0.4070(7) 0.0503(4) 0.0454(17) Uani 1 1 d . . .
H2A H 1.2247 0.4741 0.0474 0.055 Uiso 1 1 calc R . .
C3 C 1.0900(6) 0.3294(7) -0.0153(4) 0.0388(16) Uani 1 1 d . . .
H3A H 1.1094 0.3335 -0.0709 0.047 Uiso 1 1 calc R . .
C4 C 0.9925(6) 0.2445(6) 0.0150(3) 0.0287(13) Uani 1 1 d . . .
C5 C 0.9016(5) 0.1457(6) -0.0280(3) 0.0275(13) Uani 1 1 d . . .
C6 C 0.8881(5) 0.1120(6) -0.1125(3) 0.0288(13) Uani 1 1 d . . .
H6A H 0.9386 0.1515 -0.1529 0.035 Uiso 1 1 calc R . .
C7 C 0.7890(5) 0.0121(6) -0.1253(3) 0.0262(13) Uani 1 1 d . . .
C8 C 0.7369(5) -0.0219(6) -0.0499(3) 0.0254(13) Uani 1 1 d . . .
C9 C 0.6386(5) -0.1169(6) -0.0393(3) 0.0292(13) Uani 1 1 d . . .
H9A H 0.6023 -0.1606 -0.0897 0.035 Uiso 1 1 calc R . .
C10 C 0.5769(5) -0.1669(6) 0.0285(3) 0.0249(13) Uani 1 1 d . . .
C11 C 0.4758(6) -0.2686(5) 0.0274(3) 0.0258(13) Uani 1 1 d . . .
C12 C 0.4448(6) -0.2822(6) 0.1082(3) 0.0314(14) Uani 1 1 d . . .
H12A H 0.3781 -0.3440 0.1257 0.038 Uiso 1 1 calc R . .
C13 C 0.5258(5) -0.1922(6) 0.1583(3) 0.0264(13) Uani 1 1 d . . .
C14 C 0.7970(6) -0.0190(7) -0.2684(3) 0.0407(17) Uani 1 1 d . . .
H14A H 0.7513 -0.0723 -0.3154 0.061 Uiso 1 1 calc R . .
H14B H 0.8957 -0.0422 -0.2599 0.061 Uiso 1 1 calc R . .
H14C H 0.7857 0.0809 -0.2797 0.061 Uiso 1 1 calc R . .
C15 C 0.4116(6) -0.3453(6) -0.0483(3) 0.0369(16) Uani 1 1 d . . .
H15A H 0.3428 -0.4115 -0.0329 0.055 Uiso 1 1 calc R . .
H15B H 0.4836 -0.3959 -0.0729 0.055 Uiso 1 1 calc R . .
H15C H 0.3667 -0.2784 -0.0885 0.055 Uiso 1 1 calc R . .
C16 C 0.5321(6) -0.1654(6) 0.2485(3) 0.0365(16) Uani 1 1 d . . .
H16A H 0.6023 -0.0943 0.2651 0.055 Uiso 1 1 calc R . .
H16B H 0.5563 -0.2518 0.2791 0.055 Uiso 1 1 calc R . .
H16C H 0.4418 -0.1324 0.2609 0.055 Uiso 1 1 calc R . .


_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 C7 1.347(6) . ?
O1 C14 1.439(6) . ?
N1 H1 0.99(6) . ?
N1 C1 1.360(7) . ?
N1 C4 1.390(7) . ?
N2 H2 0.92(6) . ?
N2 C5 1.362(7) . ?
N2 C8 1.412(7) . ?
N3 H3 0.84(7) . ?
N3 C13 1.357(7) . ?
N3 C10 1.393(7) . ?
C1 C2 1.379(8) . ?
C2 C3 1.383(8) . ?
C3 C4 1.389(8) . ?
C4 C5 1.420(7) . ?
C5 C6 1.405(7) . ?
C6 C7 1.359(7) . ?
C7 C8 1.425(7) . ?
C8 C9 1.350(7) . ?
C9 C10 1.407(7) . ?
C10 C11 1.385(7) . ?
C11 C12 1.394(7) . ?
C11 C15 1.504(7) . ?
C12 C13 1.368(7) . ?
C13 C16 1.487(7) . ?

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
C7 O1 C14 116.0(4) . . ?
H1 N1 C1 128(3) . . ?
H1 N1 C4 123(3) . . ?
C1 N1 C4 109.0(5) . . ?
H2 N2 C5 126(4) . . ?
H2 N2 C8 125(4) . . ?
C5 N2 C8 109.7(5) . . ?
H3 N3 C13 125(5) . . ?
H3 N3 C10 125(5) . . ?
C13 N3 C10 109.6(5) . . ?
N1 C1 C2 108.0(5) . . ?
C1 C2 C3 108.4(6) . . ?
C2 C3 C4 107.6(5) . . ?
C3 C4 N1 107.1(5) . . ?
C3 C4 C5 129.0(5) . . ?
N1 C4 C5 123.9(5) . . ?
N2 C5 C6 108.8(5) . . ?
N2 C5 C4 123.5(5) . . ?
C6 C5 C4 127.7(5) . . ?
C7 C6 C5 106.8(4) . . ?
O1 C7 C6 130.5(5) . . ?
O1 C7 C8 118.8(5) . . ?
C6 C7 C8 110.7(4) . . ?
C9 C8 N2 129.0(5) . . ?
C9 C8 C7 126.9(5) . . ?
N2 C8 C7 104.0(5) . . ?
C8 C9 C10 135.3(5) . . ?
C11 C10 N3 106.9(4) . . ?
C11 C10 C9 127.2(5) . . ?
N3 C10 C9 126.0(5) . . ?
C10 C11 C12 107.0(5) . . ?
C10 C11 C15 125.2(5) . . ?
C12 C11 C15 127.8(5) . . ?
C13 C12 C11 109.1(5) . . ?
N3 C13 C12 107.5(5) . . ?
N3 C13 C16 122.2(5) . . ?
C12 C13 C16 130.4(5) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        26.99
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.080

# Attachment 'parr_sj03_b'

data_sj03
_database_code_depnum_ccdc_archive 'CCDC 696086'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H17 N3 O'
_chemical_formula_weight         267.33

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)/c

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

_cell_length_a                   17.048(3)
_cell_length_b                   17.811(4)
_cell_length_c                   9.3594(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.61(3)
_cell_angle_gamma                90.00
_cell_volume                     2836.2(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1136
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9841
_exptl_absorpt_correction_T_max  0.9920
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(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  'Nonius KappaCCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11426
_diffrn_reflns_av_R_equivalents  0.0838
_diffrn_reflns_av_sigmaI/netI    0.1842
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.80
_diffrn_reflns_theta_max         28.98
_reflns_number_total             7352
_reflns_number_gt                2911
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Nonius Collect'
_computing_cell_refinement       Denzo
_computing_data_reduction        Denzo
_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 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. The methyl H-atom coordinates
were derived using HFIX 33 which may mean that they are not completely reliable
;

_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)+(0.0800P)²+0.0000P] 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       0.0103(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7352
_refine_ls_number_parameters     378
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2305
_refine_ls_R_factor_gt           0.0832
_refine_ls_wR_factor_ref         0.2041
_refine_ls_wR_factor_gt          0.1587
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.036
_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 1.00746(12) 0.42193(14) 0.2855(2) 0.0529(7) Uani 1 1 d . . .
N1 N 0.69398(14) 0.57234(15) 0.3119(3) 0.0389(7) Uani 1 1 d . . .
H1 H 0.685(2) 0.548(2) 0.409(5) 0.090(14) Uiso 1 1 d . . .
N2 N 0.82621(13) 0.48433(14) 0.4183(3) 0.0380(7) Uani 1 1 d . . .
N3 N 0.81709(15) 0.42142(16) 0.7134(3) 0.0372(7) Uani 1 1 d . . .
H3 H 0.7848(19) 0.4503(18) 0.663(4) 0.049(11) Uiso 1 1 d . . .
C1 C 0.64472(18) 0.62015(18) 0.2386(4) 0.0399(8) Uani 1 1 d . . .
H1A H 0.5958 0.6374 0.2694 0.048 Uiso 1 1 calc R . .
C2 C 0.67595(18) 0.63964(18) 0.1141(4) 0.0444(9) Uani 1 1 d . . .
H2A H 0.6530 0.6722 0.0429 0.053 Uiso 1 1 calc R . .
C3 C 0.74810(18) 0.60299(18) 0.1102(4) 0.0421(9) Uani 1 1 d . . .
H3A H 0.7834 0.6063 0.0359 0.051 Uiso 1 1 calc R . .
C4 C 0.75874(17) 0.56119(16) 0.2335(4) 0.0362(8) Uani 1 1 d . . .
C5 C 0.82430(17) 0.51547(17) 0.2875(4) 0.0386(8) Uani 1 1 d . . .
C6 C 0.89213(17) 0.49887(18) 0.2106(4) 0.0404(8) Uani 1 1 d . . .
H6A H 0.9029 0.5150 0.1171 0.048 Uiso 1 1 calc R . .
C7 C 0.93781(18) 0.45498(19) 0.3006(4) 0.0421(8) Uani 1 1 d . . .
C8 C 0.89783(17) 0.44553(18) 0.4319(4) 0.0402(8) Uani 1 1 d . . .
C9 C 0.92367(18) 0.40464(19) 0.5458(4) 0.0444(9) Uani 1 1 d . . .
H9A H 0.9727 0.3804 0.5367 0.053 Uiso 1 1 calc R . .
C10 C 0.88880(17) 0.39198(18) 0.6785(4) 0.0395(8) Uani 1 1 d . . .
C11 C 0.91792(17) 0.35031(18) 0.7962(4) 0.0412(8) Uani 1 1 d . . .
C12 C 0.86314(18) 0.35628(18) 0.9010(4) 0.0420(8) Uani 1 1 d . . .
H12A H 0.8678 0.3340 0.9933 0.050 Uiso 1 1 calc R . .
C13 C 0.80132(18) 0.39997(17) 0.8476(4) 0.0380(8) Uani 1 1 d . . .
C14 C 1.04196(19) 0.4366(2) 0.1526(4) 0.0499(9) Uani 1 1 d . . .
H14A H 1.0922 0.4100 0.1509 0.075 Uiso 1 1 calc R . .
H14B H 1.0508 0.4907 0.1430 0.075 Uiso 1 1 calc R . .
H14C H 1.0064 0.4192 0.0731 0.075 Uiso 1 1 calc R . .
C15 C 0.9930(2) 0.3066(2) 0.8070(4) 0.0606(11) Uani 1 1 d . . .
H15A H 0.9994 0.2826 0.9013 0.091 Uiso 1 1 calc R . .
H15B H 1.0373 0.3405 0.7944 0.091 Uiso 1 1 calc R . .
H15C H 0.9914 0.2679 0.7323 0.091 Uiso 1 1 calc R . .
C16 C 0.72824(18) 0.42272(19) 0.9139(4) 0.0466(9) Uani 1 1 d . . .
H16A H 0.6963 0.4539 0.8466 0.070 Uiso 1 1 calc R . .
H16B H 0.7417 0.4514 1.0014 0.070 Uiso 1 1 calc R . .
H16C H 0.6984 0.3779 0.9377 0.070 Uiso 1 1 calc R . .
O1' O 0.48268(11) 0.50151(11) 0.7643(2) 0.0413(6) Uani 1 1 d . . .
N1' N 0.79650(14) 0.61618(16) 0.6053(3) 0.0416(7) Uani 1 1 d . . .
H1' H 0.8061(19) 0.5787(19) 0.547(4) 0.051(11) Uiso 1 1 d . . .
N2' N 0.66665(13) 0.51275(14) 0.5997(3) 0.0347(6) Uani 1 1 d . . .
N3' N 0.68064(15) 0.37301(15) 0.4216(3) 0.0391(7) Uani 1 1 d . . .
H3' H 0.714(2) 0.412(2) 0.442(4) 0.059(11) Uiso 1 1 d . . .
C1' C 0.84658(18) 0.67507(18) 0.6262(4) 0.0470(9) Uani 1 1 d . . .
H1'A H 0.8953 0.6812 0.5836 0.056 Uiso 1 1 calc R . .
C2' C 0.81494(19) 0.7238(2) 0.7185(4) 0.0535(10) Uani 1 1 d . . .
H2'A H 0.8377 0.7697 0.7521 0.064 Uiso 1 1 calc R . .
C3' C 0.74323(19) 0.69433(17) 0.7551(4) 0.0445(9) Uani 1 1 d . . .
H3'A H 0.7085 0.7164 0.8186 0.053 Uiso 1 1 calc R . .
C4' C 0.73157(16) 0.62741(17) 0.6828(3) 0.0366(8) Uani 1 1 d . . .
C5' C 0.66726(16) 0.57541(17) 0.6789(3) 0.0355(8) Uani 1 1 d . . .
C6' C 0.59754(16) 0.58453(18) 0.7559(3) 0.0366(8) Uani 1 1 d . . .
H6'A H 0.5855 0.6249 0.8173 0.044 Uiso 1 1 calc R . .
C7' C 0.55276(16) 0.52376(17) 0.7228(3) 0.0346(7) Uani 1 1 d . . .
C8' C 0.59538(16) 0.47761(17) 0.6244(3) 0.0346(8) Uani 1 1 d . . .
C9' C 0.57027(17) 0.41086(17) 0.5679(3) 0.0362(8) Uani 1 1 d . . .
H9'A H 0.5199 0.3951 0.5940 0.043 Uiso 1 1 calc R . .
C10' C 0.60791(17) 0.36146(17) 0.4761(3) 0.0359(8) Uani 1 1 d . . .
C11' C 0.57990(18) 0.29261(17) 0.4209(3) 0.0396(8) Uani 1 1 d . . .
C12' C 0.63619(19) 0.26519(19) 0.3315(4) 0.0450(9) Uani 1 1 d . . .
H12B H 0.6323 0.2200 0.2777 0.054 Uiso 1 1 calc R . .
C13' C 0.69836(18) 0.31514(18) 0.3349(4) 0.0397(8) Uani 1 1 d . . .
C14' C 0.44534(18) 0.55214(19) 0.8583(4) 0.0444(9) Uani 1 1 d . . .
H14D H 0.3947 0.5312 0.8825 0.067 Uiso 1 1 calc R . .
H14E H 0.4368 0.6007 0.8106 0.067 Uiso 1 1 calc R . .
H14F H 0.4790 0.5591 0.9461 0.067 Uiso 1 1 calc R . .
C15' C 0.50370(19) 0.25641(19) 0.4526(4) 0.0556(10) Uani 1 1 d . . .
H15D H 0.4977 0.2091 0.3996 0.083 Uiso 1 1 calc R . .
H15E H 0.4601 0.2901 0.4236 0.083 Uiso 1 1 calc R . .
H15F H 0.5033 0.2463 0.5555 0.083 Uiso 1 1 calc R . .
C16' C 0.7734(2) 0.3112(2) 0.2629(4) 0.0547(10) Uani 1 1 d . . .
H16D H 0.8048 0.3561 0.2865 0.082 Uiso 1 1 calc R . .
H16E H 0.7623 0.3084 0.1590 0.082 Uiso 1 1 calc R . .
H16F H 0.8027 0.2664 0.2957 0.082 Uiso 1 1 calc R . .


_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 C7 1.341(4) . ?
O1 C14 1.432(4) . ?
N1 H1 1.03(4) . ?
N1 C1 1.352(4) . ?
N1 C4 1.378(4) . ?
N2 C5 1.343(4) . ?
N2 C8 1.402(4) . ?
N3 H3 0.87(3) . ?
N3 C13 1.356(4) . ?
N3 C10 1.388(4) . ?
C1 C2 1.356(4) . ?
C2 C3 1.395(4) . ?
C3 C4 1.376(4) . ?
C4 C5 1.448(4) . ?
C5 C6 1.431(4) . ?
C6 C7 1.358(4) . ?
C7 C8 1.452(4) . ?
C8 C9 1.342(4) . ?
C9 C10 1.428(4) . ?
C10 C11 1.394(4) . ?
C11 C12 1.400(4) . ?
C11 C15 1.496(4) . ?
C12 C13 1.378(4) . ?
C13 C16 1.483(4) . ?
O1' C7' 1.339(3) . ?
O1' C14' 1.437(3) . ?
N1' H1' 0.88(3) . ?
N1' C1' 1.359(4) . ?
N1' C4' 1.376(4) . ?
N2' C5' 1.339(4) . ?
N2' C8' 1.399(3) . ?
N3' H3' 0.91(4) . ?
N3' C13' 1.358(4) . ?
N3' C10' 1.386(4) . ?
C1' C2' 1.360(5) . ?
C2' C3' 1.393(4) . ?
C3' C4' 1.379(4) . ?
C4' C5' 1.434(4) . ?
C5' C6' 1.438(4) . ?
C6' C7' 1.349(4) . ?
C7' C8' 1.462(4) . ?
C8' C9' 1.360(4) . ?
C9' C10' 1.412(4) . ?
C10' C11' 1.403(4) . ?
C11' C12' 1.400(4) . ?
C11' C15' 1.497(4) . ?
C12' C13' 1.383(4) . ?
C13' C16' 1.485(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
C7 O1 C14 115.2(3) . . ?
H1 N1 C1 126(2) . . ?
H1 N1 C4 125(2) . . ?
C1 N1 C4 108.3(3) . . ?
C5 N2 C8 104.9(2) . . ?
H3 N3 C13 121(2) . . ?
H3 N3 C10 129(2) . . ?
C13 N3 C10 109.9(3) . . ?
N1 C1 C2 109.4(3) . . ?
C1 C2 C3 107.3(3) . . ?
C4 C3 C2 107.5(3) . . ?
N1 C4 C3 107.5(3) . . ?
N1 C4 C5 121.5(3) . . ?
C3 C4 C5 130.9(3) . . ?
N2 C5 C6 113.5(3) . . ?
N2 C5 C4 121.6(3) . . ?
C6 C5 C4 124.8(3) . . ?
C7 C6 C5 104.9(3) . . ?
O1 C7 C6 131.6(3) . . ?
O1 C7 C8 120.3(3) . . ?
C6 C7 C8 108.1(3) . . ?
C9 C8 N2 125.5(3) . . ?
C9 C8 C7 125.9(3) . . ?
N2 C8 C7 108.6(3) . . ?
C8 C9 C10 130.0(3) . . ?
N3 C10 C11 106.9(3) . . ?
N3 C10 C9 124.5(3) . . ?
C11 C10 C9 128.6(3) . . ?
C10 C11 C12 107.1(3) . . ?
C10 C11 C15 126.3(3) . . ?
C12 C11 C15 126.7(3) . . ?
C13 C12 C11 108.5(3) . . ?
N3 C13 C12 107.7(3) . . ?
N3 C13 C16 122.1(3) . . ?
C12 C13 C16 130.2(3) . . ?
C7' O1' C14' 115.4(2) . . ?
H1' N1' C1' 122(2) . . ?
H1' N1' C4' 128(2) . . ?
C1' N1' C4' 109.3(3) . . ?
C5' N2' C8' 104.9(2) . . ?
H3' N3' C13' 123(2) . . ?
H3' N3' C10' 127(2) . . ?
C13' N3' C10' 110.2(3) . . ?
N1' C1' C2' 108.3(3) . . ?
C1' C2' C3' 107.8(3) . . ?
C4' C3' C2' 107.8(3) . . ?
N1' C4' C3' 106.8(3) . . ?
N1' C4' C5' 122.1(3) . . ?
C3' C4' C5' 131.1(3) . . ?
N2' C5' C4' 122.1(3) . . ?
N2' C5' C6' 113.2(3) . . ?
C4' C5' C6' 124.7(3) . . ?
C7' C6' C5' 105.5(3) . . ?
O1' C7' C6' 132.3(3) . . ?
O1' C7' C8' 120.3(3) . . ?
C6' C7' C8' 107.4(3) . . ?
C9' C8' N2' 125.6(3) . . ?
C9' C8' C7' 125.5(3) . . ?
N2' C8' C7' 108.9(3) . . ?
C8' C9' C10' 129.6(3) . . ?
N3' C10' C11' 106.6(3) . . ?
N3' C10' C9' 125.7(3) . . ?
C11' C10' C9' 127.7(3) . . ?
C12' C11' C10' 107.1(3) . . ?
C12' C11' C15' 127.2(3) . . ?
C10' C11' C15' 125.7(3) . . ?
C13' C12' C11' 108.4(3) . . ?
N3' C13' C12' 107.6(3) . . ?
N3' C13' C16' 122.5(3) . . ?
C12' C13' C16' 129.8(3) . . ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        28.98
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.055


