# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               'RSC Advances'
_journal_coden_cambridge         1500
#TrackingRef 'CCDC.cif'

#==========================================================================

# SUBMISSION DETAILS

_publ_contact_author_name        'Pro. Jun Lin'
_publ_contact_author_address     
;
Key Laboratory of Medicinal Chemistry for Natural Resource
(Yunnan University), Ministry Education, School of Chemical Science
and Technology, Yunnan University, Kunming, 650091, P. R. China
;
_publ_contact_author_email       linjun@ynu.edu.cn
_publ_contact_author_fax         '+86 871 5033215'
_publ_contact_author_phone       '+86 871 5033215'
_publ_requested_category         ?
_publ_requested_coeditor_name    ?

#==========================================================================

# TITLE AND AUTHOR LIST

_publ_section_title              
;
Three-component solvent-free synthesis of highly substituted bicyclic
pyridines containing a ring-junction nitrogen. part II:
tetrahydro-imidazo[1,2-a]pyridine ring systems

;

_publ_section_title_footnote     .

loop_
_publ_author_name
_publ_author_footnote
_publ_author_address

'Fu-Chao Yu' .
;Key Laboratory of Medicinal Chemistry for Natural Resource
(Yunnan University), Ministry Education, School of Chemical Science
and Technology, Yunnan University, Kunming, 650091, P. R. China
;
'Sheng-Jiao Yan' .
;Key Laboratory of Medicinal Chemistry for Natural Resource
(Yunnan University), Ministry Education, School of Chemical Science
and Technology, Yunnan University, Kunming, 650091, P. R. China
;
'Rong Huang' .
;Key Laboratory of Medicinal Chemistry for Natural Resource
(Yunnan University), Ministry Education, School of Chemical Science
and Technology, Yunnan University, Kunming, 650091, P. R. China
;
'Ya-Juang Tang' .
;Key Laboratory of Medicinal Chemistry for Natural Resource
(Yunnan University), Ministry Education, School of Chemical Science
and Technology, Yunnan University, Kunming, 650091, P. R. China
;
'Jun Lin' .
;Key Laboratory of Medicinal Chemistry for Natural Resource
(Yunnan University), Ministry Education, School of Chemical Science
and Technology, Yunnan University, Kunming, 650091, P. R. China
;

#==========================================================================

data_100112a_0m
_database_code_depnum_ccdc_archive 'CCDC 818211'
#TrackingRef 'CCDC.cif'

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

(4-chlorophenyl)(1,2,3,5-tetrahydro-5-(4-methoxyphenyl)
-6-nitroimidazo[1,2-a]pyridin-8-yl)methanone

;

_chemical_name_common            
;

(4-chlorophenyl)(1,2,3,5-tetrahydro-5-(4-methoxyphenyl)
-6-nitroimidazo[1,2-a]pyridin-8-yl)methanone

;

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            'C21 H18 Cl N3 O4'

_chemical_formula_weight         411.83

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                   8.587(5)

_cell_length_b                   18.369(5)

_cell_length_c                   12.335(5)

_cell_angle_alpha                90.000(5)

_cell_angle_beta                 92.329(5)

_cell_angle_gamma                90.000(5)

_cell_volume                     1944.0(15)

_cell_formula_units_Z            4

_cell_measurement_temperature    293(2)

_cell_measurement_reflns_used    1635

_cell_measurement_theta_min      2.22

_cell_measurement_theta_max      20.52

_exptl_crystal_description       block

_exptl_crystal_colour            yellow

_exptl_crystal_size_max          0.34

_exptl_crystal_size_mid          0.29

_exptl_crystal_size_min          0.15

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.407

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             856

_exptl_absorpt_coefficient_mu    0.230

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.9456

_exptl_absorpt_correction_T_max  0.9784

_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;

?

;

_diffrn_ambient_temperature      293(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            13201

_diffrn_reflns_av_R_equivalents  0.0509

_diffrn_reflns_av_sigmaI/netI    0.0727

_diffrn_reflns_limit_h_min       -9

_diffrn_reflns_limit_h_max       11

_diffrn_reflns_limit_k_min       -23

_diffrn_reflns_limit_k_max       23

_diffrn_reflns_limit_l_min       -15

_diffrn_reflns_limit_l_max       16

_diffrn_reflns_theta_min         1.99

_diffrn_reflns_theta_max         28.40

_reflns_number_total             4601

_reflns_number_gt                1993

_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^)+(0.0630P)^2^+0.0000P] 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     SHELXL

_refine_ls_extinction_coef       0.0163(16)

_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^

_refine_ls_number_reflns         4601

_refine_ls_number_parameters     264

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.1427

_refine_ls_R_factor_gt           0.0479

_refine_ls_wR_factor_ref         0.1450

_refine_ls_wR_factor_gt          0.1085

_refine_ls_goodness_of_fit_ref   0.937

_refine_ls_restrained_S_all      0.937

_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

C1 C 0.4150(3) 0.17981(16) 0.6739(2) 0.0692(7) Uani 1 1 d . . .
Cl1 Cl 0.28789(11) 0.22215(5) 0.76028(7) 0.1198(4) Uani 1 1 d . . .
N1 N 0.9383(2) -0.00295(11) 0.32209(16) 0.0683(6) Uani 1 1 d . . .
H1 H 0.9755 -0.0005 0.3878 0.082 Uiso 1 1 calc R . .
O1 O 0.8336(2) 0.03988(10) 0.51385(14) 0.0775(6) Uani 1 1 d . . .
C2 C 0.4545(3) 0.21408(14) 0.5798(2) 0.0711(7) Uani 1 1 d . . .
H2 H 0.4165 0.2604 0.5636 0.085 Uiso 1 1 calc R . .
N2 N 0.7856(2) 0.01955(10) 0.18016(15) 0.0615(6) Uani 1 1 d . . .
O2 O 0.9724(2) 0.28808(11) -0.11471(15) 0.0855(6) Uani 1 1 d . . .
C3 C 0.5510(3) 0.17917(13) 0.5096(2) 0.0607(7) Uani 1 1 d . . .
H3 H 0.5768 0.2018 0.4453 0.073 Uiso 1 1 calc R . .
N3 N 0.3927(3) 0.09126(11) 0.1319(2) 0.0729(6) Uani 1 1 d . . .
O3 O 0.3849(2) 0.09213(10) 0.03066(17) 0.0872(6) Uani 1 1 d . . .
C4 C 0.6099(3) 0.11047(12) 0.53420(18) 0.0520(6) Uani 1 1 d . . .
O4 O 0.2765(2) 0.09869(12) 0.18717(19) 0.1012(7) Uani 1 1 d . . .
C5 C 0.5710(3) 0.07826(13) 0.63113(19) 0.0604(7) Uani 1 1 d . . .
H5 H 0.6127 0.0331 0.6499 0.072 Uiso 1 1 calc R . .
C6 C 0.4718(3) 0.11192(15) 0.6998(2) 0.0664(7) Uani 1 1 d . . .
H6 H 0.4435 0.0890 0.7633 0.080 Uiso 1 1 calc R . .
C7 C 0.7222(3) 0.07104(13) 0.4656(2) 0.0571(6) Uani 1 1 d . . .
C8 C 0.6992(3) 0.06766(12) 0.35010(19) 0.0527(6) Uani 1 1 d . . .
C9 C 0.5604(3) 0.08748(12) 0.2925(2) 0.0577(6) Uani 1 1 d . . .
H9 H 0.4779 0.1055 0.3310 0.069 Uiso 1 1 calc R . .
C10 C 0.5428(3) 0.08125(12) 0.1832(2) 0.0582(6) Uani 1 1 d . . .
C11 C 0.6741(3) 0.06109(13) 0.11124(19) 0.0628(7) Uani 1 1 d . . .
H11 H 0.6317 0.0281 0.0550 0.075 Uiso 1 1 calc R . .
C12 C 0.8084(3) 0.02982(12) 0.28696(19) 0.0562(6) Uani 1 1 d . . .
C13 C 1.0109(3) -0.04369(15) 0.2359(2) 0.0761(8) Uani 1 1 d . . .
H13A H 0.9980 -0.0957 0.2454 0.091 Uiso 1 1 calc R . .
H13B H 1.1210 -0.0325 0.2330 0.091 Uiso 1 1 calc R . .
C14 C 0.9213(3) -0.01674(16) 0.1350(2) 0.0760(8) Uani 1 1 d . . .
H14A H 0.9830 0.0172 0.0945 0.091 Uiso 1 1 calc R . .
H14B H 0.8894 -0.0569 0.0881 0.091 Uiso 1 1 calc R . .
C15 C 0.7524(3) 0.12418(13) 0.05449(18) 0.0582(6) Uani 1 1 d . . .
C16 C 0.8520(3) 0.17140(15) 0.1091(2) 0.0729(8) Uani 1 1 d . . .
H16 H 0.8682 0.1662 0.1838 0.087 Uiso 1 1 calc R . .
C17 C 0.9288(3) 0.22629(15) 0.0564(2) 0.0736(8) Uani 1 1 d . . .
H17 H 0.9967 0.2570 0.0952 0.088 Uiso 1 1 calc R . .
C18 C 0.9042(3) 0.23536(15) -0.0537(2) 0.0634(7) Uani 1 1 d . . .
C19 C 0.8028(3) 0.18950(15) -0.1095(2) 0.0713(8) Uani 1 1 d . . .
H19 H 0.7835 0.1960 -0.1836 0.086 Uiso 1 1 calc R . .
C20 C 0.7300(3) 0.13416(15) -0.0565(2) 0.0674(7) Uani 1 1 d . . .
H20 H 0.6642 0.1027 -0.0958 0.081 Uiso 1 1 calc R . .
C21 C 1.0905(3) 0.33194(17) -0.0633(3) 0.0963(10) Uani 1 1 d . . .
H21A H 1.0466 0.3594 -0.0058 0.144 Uiso 1 1 calc R . .
H21B H 1.1321 0.3647 -0.1155 0.144 Uiso 1 1 calc R . .
H21C H 1.1723 0.3013 -0.0340 0.144 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

C1 0.0644(17) 0.081(2) 0.0618(18) -0.0191(15) -0.0006(13) 0.0011(15)
Cl1 0.1251(8) 0.1406(8) 0.0950(7) -0.0312(5) 0.0209(5) 0.0400(6)
N1 0.0643(14) 0.0878(15) 0.0520(13) -0.0057(11) -0.0070(10) 0.0195(12)
O1 0.0652(11) 0.1101(15) 0.0568(11) 0.0098(10) -0.0011(9) 0.0241(11)
C2 0.0786(19) 0.0555(16) 0.078(2) -0.0069(14) -0.0063(16) 0.0018(14)
N2 0.0673(14) 0.0662(13) 0.0502(13) -0.0032(10) -0.0080(10) 0.0136(11)
O2 0.0851(14) 0.0959(15) 0.0758(13) 0.0208(11) 0.0080(11) 0.0094(12)
C3 0.0643(16) 0.0600(16) 0.0577(15) 0.0039(13) 0.0004(13) -0.0100(13)
N3 0.0726(17) 0.0638(15) 0.0797(18) -0.0077(12) -0.0271(14) 0.0049(12)
O3 0.0934(15) 0.0888(14) 0.0759(14) -0.0126(11) -0.0389(11) 0.0076(11)
C4 0.0495(14) 0.0538(15) 0.0524(14) 0.0028(12) -0.0034(11) -0.0072(12)
O4 0.0592(13) 0.132(2) 0.1106(17) -0.0156(14) -0.0166(12) 0.0097(12)
C5 0.0589(16) 0.0628(16) 0.0593(16) 0.0091(13) 0.0008(13) -0.0022(13)
C6 0.0646(17) 0.0820(19) 0.0530(15) 0.0043(14) 0.0041(13) -0.0028(15)
C7 0.0538(15) 0.0629(16) 0.0542(16) 0.0064(12) -0.0003(12) -0.0030(13)
C8 0.0487(14) 0.0573(14) 0.0517(15) 0.0015(11) -0.0038(11) 0.0024(12)
C9 0.0552(15) 0.0521(15) 0.0655(17) -0.0042(12) -0.0017(12) -0.0017(12)
C10 0.0558(16) 0.0554(15) 0.0618(17) -0.0016(12) -0.0160(13) 0.0003(12)
C11 0.0717(18) 0.0626(16) 0.0524(15) -0.0071(12) -0.0187(13) 0.0055(14)
C12 0.0574(16) 0.0585(15) 0.0522(15) 0.0046(12) -0.0042(12) 0.0009(13)
C13 0.0774(19) 0.086(2) 0.0642(18) -0.0043(15) 0.0008(15) 0.0212(16)
C14 0.0818(19) 0.085(2) 0.0606(17) -0.0115(14) -0.0024(14) 0.0184(16)
C15 0.0712(17) 0.0601(15) 0.0426(14) -0.0048(12) -0.0075(12) 0.0068(13)
C16 0.090(2) 0.084(2) 0.0438(15) -0.0005(14) -0.0111(14) -0.0068(17)
C17 0.0799(19) 0.0830(19) 0.0569(17) 0.0018(14) -0.0107(14) -0.0090(16)
C18 0.0642(17) 0.0718(18) 0.0541(16) 0.0018(14) 0.0006(13) 0.0164(15)
C19 0.093(2) 0.0784(19) 0.0415(15) 0.0002(14) -0.0054(14) 0.0229(17)
C20 0.0833(19) 0.0692(18) 0.0484(16) -0.0090(13) -0.0150(13) 0.0100(15)
C21 0.083(2) 0.097(2) 0.109(3) 0.018(2) 0.0124(19) 0.0002(19)

_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

C1 C6 1.372(3) . ?
C1 C2 1.374(4) . ?
C1 Cl1 1.740(3) . ?
N1 C12 1.325(3) . ?
N1 C13 1.460(3) . ?
N1 H1 0.8600 . ?
O1 C7 1.245(3) . ?
C2 C3 1.382(3) . ?
C2 H2 0.9300 . ?
N2 C12 1.337(3) . ?
N2 C11 1.468(3) . ?
N2 C14 1.471(3) . ?
O2 C18 1.372(3) . ?
O2 C21 1.424(3) . ?
C3 C4 1.389(3) . ?
C3 H3 0.9300 . ?
N3 O4 1.239(3) . ?
N3 O3 1.248(3) . ?
N3 C10 1.425(3) . ?
C4 C5 1.387(3) . ?
C4 C7 1.495(3) . ?
C5 C6 1.372(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.432(3) . ?
C8 C9 1.410(3) . ?
C8 C12 1.424(3) . ?
C9 C10 1.355(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.509(3) . ?
C11 C15 1.524(3) . ?
C11 H11 0.9800 . ?
C13 C14 1.519(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.375(3) . ?
C15 C20 1.387(3) . ?
C16 C17 1.382(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.377(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.376(3) . ?
C19 C20 1.373(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

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

C6 C1 C2 121.0(2) . . ?
C6 C1 Cl1 119.3(2) . . ?
C2 C1 Cl1 119.7(2) . . ?
C12 N1 C13 111.9(2) . . ?
C12 N1 H1 124.0 . . ?
C13 N1 H1 124.0 . . ?
C1 C2 C3 119.5(3) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C12 N2 C11 124.3(2) . . ?
C12 N2 C14 110.50(19) . . ?
C11 N2 C14 121.6(2) . . ?
C18 O2 C21 117.9(2) . . ?
C2 C3 C4 120.5(2) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
O4 N3 O3 122.5(2) . . ?
O4 N3 C10 120.3(2) . . ?
O3 N3 C10 117.2(3) . . ?
C5 C4 C3 118.5(2) . . ?
C5 C4 C7 117.7(2) . . ?
C3 C4 C7 123.6(2) . . ?
C6 C5 C4 121.2(2) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C1 C6 C5 119.3(2) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
O1 C7 C8 121.9(2) . . ?
O1 C7 C4 116.9(2) . . ?
C8 C7 C4 121.2(2) . . ?
C9 C8 C12 114.3(2) . . ?
C9 C8 C7 124.8(2) . . ?
C12 C8 C7 119.9(2) . . ?
C10 C9 C8 122.5(2) . . ?
C10 C9 H9 118.7 . . ?
C8 C9 H9 118.7 . . ?
C9 C10 N3 119.6(2) . . ?
C9 C10 C11 123.4(2) . . ?
N3 C10 C11 117.0(2) . . ?
N2 C11 C10 105.8(2) . . ?
N2 C11 C15 111.8(2) . . ?
C10 C11 C15 116.0(2) . . ?
N2 C11 H11 107.7 . . ?
C10 C11 H11 107.7 . . ?
C15 C11 H11 107.7 . . ?
N1 C12 N2 110.2(2) . . ?
N1 C12 C8 127.4(2) . . ?
N2 C12 C8 122.3(2) . . ?
N1 C13 C14 102.3(2) . . ?
N1 C13 H13A 111.3 . . ?
C14 C13 H13A 111.3 . . ?
N1 C13 H13B 111.3 . . ?
C14 C13 H13B 111.3 . . ?
H13A C13 H13B 109.2 . . ?
N2 C14 C13 102.7(2) . . ?
N2 C14 H14A 111.2 . . ?
C13 C14 H14A 111.2 . . ?
N2 C14 H14B 111.2 . . ?
C13 C14 H14B 111.2 . . ?
H14A C14 H14B 109.1 . . ?
C16 C15 C20 117.3(2) . . ?
C16 C15 C11 122.1(2) . . ?
C20 C15 C11 120.5(2) . . ?
C15 C16 C17 121.9(2) . . ?
C15 C16 H16 119.0 . . ?
C17 C16 H16 119.0 . . ?
C18 C17 C16 119.8(3) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
O2 C18 C19 115.7(2) . . ?
O2 C18 C17 125.1(3) . . ?
C19 C18 C17 119.2(3) . . ?
C20 C19 C18 120.4(2) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C15 121.4(3) . . ?
C19 C20 H20 119.3 . . ?
C15 C20 H20 119.3 . . ?
O2 C21 H21A 109.5 . . ?
O2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

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

C6 C1 C2 C3 1.0(4) . . . . ?
Cl1 C1 C2 C3 -177.73(18) . . . . ?
C1 C2 C3 C4 -1.0(4) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C2 C3 C4 C7 -176.3(2) . . . . ?
C3 C4 C5 C6 2.4(3) . . . . ?
C7 C4 C5 C6 178.3(2) . . . . ?
C2 C1 C6 C5 0.7(4) . . . . ?
Cl1 C1 C6 C5 179.42(19) . . . . ?
C4 C5 C6 C1 -2.4(4) . . . . ?
C5 C4 C7 O1 -39.3(3) . . . . ?
C3 C4 C7 O1 136.4(2) . . . . ?
C5 C4 C7 C8 138.8(2) . . . . ?
C3 C4 C7 C8 -45.5(3) . . . . ?
O1 C7 C8 C9 165.5(2) . . . . ?
C4 C7 C8 C9 -12.6(4) . . . . ?
O1 C7 C8 C12 -2.1(4) . . . . ?
C4 C7 C8 C12 179.8(2) . . . . ?
C12 C8 C9 C10 -9.8(3) . . . . ?
C7 C8 C9 C10 -178.0(2) . . . . ?
C8 C9 C10 N3 170.2(2) . . . . ?
C8 C9 C10 C11 -7.4(4) . . . . ?
O4 N3 C10 C9 -6.9(4) . . . . ?
O3 N3 C10 C9 173.1(2) . . . . ?
O4 N3 C10 C11 170.8(2) . . . . ?
O3 N3 C10 C11 -9.2(3) . . . . ?
C12 N2 C11 C10 -30.6(3) . . . . ?
C14 N2 C11 C10 172.9(2) . . . . ?
C12 N2 C11 C15 96.5(3) . . . . ?
C14 N2 C11 C15 -60.0(3) . . . . ?
C9 C10 C11 N2 25.5(3) . . . . ?
N3 C10 C11 N2 -152.1(2) . . . . ?
C9 C10 C11 C15 -99.1(3) . . . . ?
N3 C10 C11 C15 83.3(3) . . . . ?
C13 N1 C12 N2 -3.6(3) . . . . ?
C13 N1 C12 C8 172.9(2) . . . . ?
C11 N2 C12 N1 -165.7(2) . . . . ?
C14 N2 C12 N1 -7.0(3) . . . . ?
C11 N2 C12 C8 17.5(4) . . . . ?
C14 N2 C12 C8 176.3(2) . . . . ?
C9 C8 C12 N1 -171.0(2) . . . . ?
C7 C8 C12 N1 -2.1(4) . . . . ?
C9 C8 C12 N2 5.2(3) . . . . ?
C7 C8 C12 N2 174.0(2) . . . . ?
C12 N1 C13 C14 11.9(3) . . . . ?
C12 N2 C14 C13 13.8(3) . . . . ?
C11 N2 C14 C13 173.3(2) . . . . ?
N1 C13 C14 N2 -14.6(3) . . . . ?
N2 C11 C15 C16 -47.5(3) . . . . ?
C10 C11 C15 C16 73.9(3) . . . . ?
N2 C11 C15 C20 129.9(2) . . . . ?
C10 C11 C15 C20 -108.8(3) . . . . ?
C20 C15 C16 C17 -0.7(4) . . . . ?
C11 C15 C16 C17 176.7(2) . . . . ?
C15 C16 C17 C18 1.0(4) . . . . ?
C21 O2 C18 C19 -173.5(2) . . . . ?
C21 O2 C18 C17 7.3(4) . . . . ?
C16 C17 C18 O2 179.4(2) . . . . ?
C16 C17 C18 C19 0.2(4) . . . . ?
O2 C18 C19 C20 179.1(2) . . . . ?
C17 C18 C19 C20 -1.6(4) . . . . ?
C18 C19 C20 C15 2.0(4) . . . . ?
C16 C15 C20 C19 -0.8(4) . . . . ?
C11 C15 C20 C19 -178.2(2) . . . . ?

loop_

_geom_hbond_atom_site_label_D

_geom_hbond_atom_site_label_H

_geom_hbond_atom_site_label_A

_geom_hbond_distance_DH

_geom_hbond_distance_HA

_geom_hbond_distance_DA

_geom_hbond_angle_DHA

_geom_hbond_site_symmetry_A

C11 H11 O3 0.98 2.45 3.342(3) 151.2 3_655
N1 H1 O1 0.86 2.13 2.841(3) 140.2 3_756
N1 H1 O1 0.86 2.15 2.683(3) 120.0 .

_diffrn_measured_fraction_theta_max 0.962

_diffrn_reflns_theta_full        28.40

_diffrn_measured_fraction_theta_full 0.962

_refine_diff_density_max         0.153

_refine_diff_density_min         -0.188

_refine_diff_density_rms         0.035