# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_email       panlingnenu@yahoo.com.cn
_publ_contact_author_name        'Ling Pan'
loop_
_publ_author_name
'Yu Zhang'
'Ling Pan'
'Xianxiu Xu'
'Qun Liu'

data_2-H-pyrroles4a
_database_code_depnum_ccdc_archive 'CCDC 844259'
#TrackingRef '2-H-pyrroles4a.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H17 N O2'
_chemical_formula_weight         279.33

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   P21/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                   7.6540(13)
_cell_length_b                   16.830(3)
_cell_length_c                   11.568(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.578(2)
_cell_angle_gamma                90.00
_cell_volume                     1469.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       bulk
_exptl_crystal_colour            pale-yellow
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9829
_exptl_absorpt_correction_T_max  0.9878
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_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       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7868
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_sigmaI/netI    0.0485
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         25.93
_reflns_number_total             2863
_reflns_number_gt                1784
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_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^)+(0.0572P)^2^+0.0310P] 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       0.025(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         2863
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1242
_refine_ls_wR_factor_gt          0.1091
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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
O1 O 1.13253(17) 0.04650(7) 0.75956(11) 0.0505(4) Uani 1 1 d . . .
N1 N 0.8049(2) 0.06502(9) 0.49943(13) 0.0480(4) Uani 1 1 d . . .
C17 C 1.0477(2) 0.08265(12) 0.66303(16) 0.0438(5) Uani 1 1 d . . .
C16 C 0.8769(2) 0.04077(10) 0.61917(16) 0.0429(5) Uani 1 1 d . . .
H16 H 0.9005 -0.0165 0.6190 0.051 Uiso 1 1 calc R . .
C6 C 0.7858(2) 0.10173(10) 0.80903(16) 0.0395(4) Uani 1 1 d . . .
C10 C 0.5442(2) 0.12318(10) 0.38507(17) 0.0416(5) Uani 1 1 d . . .
O2 O 1.10170(19) 0.14148(9) 0.62200(13) 0.0680(5) Uani 1 1 d . . .
C9 C 0.6501(2) 0.09383(10) 0.49494(16) 0.0409(4) Uani 1 1 d . . .
C7 C 0.7285(2) 0.05622(11) 0.69674(16) 0.0461(5) Uani 1 1 d . . .
H7 H 0.6844 0.0044 0.7176 0.055 Uiso 1 1 calc R . .
C11 C 0.3799(2) 0.15816(12) 0.38454(19) 0.0551(6) Uani 1 1 d . . .
H11 H 0.3344 0.1623 0.4540 0.066 Uiso 1 1 calc R . .
C5 C 0.8168(3) 0.18318(11) 0.81000(18) 0.0498(5) Uani 1 1 d . . .
H5 H 0.7985 0.2114 0.7399 0.060 Uiso 1 1 calc R . .
C15 C 0.6068(3) 0.11731(11) 0.27976(17) 0.0492(5) Uani 1 1 d . . .
H15 H 0.7165 0.0939 0.2783 0.059 Uiso 1 1 calc R . .
C4 C 0.8747(3) 0.22268(13) 0.9142(2) 0.0594(6) Uani 1 1 d . . .
H4 H 0.8950 0.2771 0.9134 0.071 Uiso 1 1 calc R . .
C8 C 0.5821(2) 0.09549(13) 0.60916(17) 0.0554(6) Uani 1 1 d . . .
H8A H 0.4721 0.0660 0.6035 0.067 Uiso 1 1 calc R . .
H8B H 0.5619 0.1497 0.6323 0.067 Uiso 1 1 calc R . .
C1 C 0.8137(3) 0.06264(12) 0.91561(18) 0.0525(5) Uani 1 1 d . . .
H1 H 0.7923 0.0083 0.9176 0.063 Uiso 1 1 calc R . .
C14 C 0.5091(3) 0.14568(13) 0.17671(18) 0.0597(6) Uani 1 1 d . . .
H14 H 0.5527 0.1409 0.1066 0.072 Uiso 1 1 calc R . .
C3 C 0.9025(3) 0.18230(15) 1.0186(2) 0.0645(6) Uani 1 1 d . . .
H3 H 0.9415 0.2091 1.0884 0.077 Uiso 1 1 calc R . .
C2 C 0.8723(3) 0.10232(15) 1.01912(19) 0.0641(6) Uani 1 1 d . . .
H2 H 0.8915 0.0745 1.0896 0.077 Uiso 1 1 calc R . .
C13 C 0.3469(3) 0.18104(13) 0.1779(2) 0.0646(6) Uani 1 1 d . . .
H13 H 0.2813 0.2008 0.1090 0.078 Uiso 1 1 calc R . .
C18 C 1.2797(3) 0.08719(14) 0.82762(19) 0.0674(6) Uani 1 1 d . . .
H18A H 1.3279 0.0552 0.8941 0.101 Uiso 1 1 calc R . .
H18B H 1.2404 0.1371 0.8542 0.101 Uiso 1 1 calc R . .
H18C H 1.3693 0.0964 0.7801 0.101 Uiso 1 1 calc R . .
C12 C 0.2832(3) 0.18685(13) 0.2811(2) 0.0669(7) Uani 1 1 d . . .
H12 H 0.1735 0.2104 0.2820 0.080 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
O1 0.0465(8) 0.0598(8) 0.0430(8) 0.0037(7) 0.0006(6) 0.0047(6)
N1 0.0477(10) 0.0549(10) 0.0405(10) -0.0036(8) 0.0049(7) 0.0101(7)
C17 0.0447(11) 0.0483(11) 0.0393(12) 0.0002(9) 0.0099(9) 0.0072(9)
C16 0.0474(11) 0.0400(10) 0.0404(12) -0.0018(8) 0.0050(9) 0.0063(8)
C6 0.0348(10) 0.0444(11) 0.0400(11) -0.0006(9) 0.0084(8) 0.0007(8)
C10 0.0404(11) 0.0397(10) 0.0430(12) -0.0069(8) 0.0018(9) -0.0013(8)
O2 0.0641(10) 0.0717(10) 0.0660(11) 0.0192(8) 0.0045(8) -0.0131(8)
C9 0.0384(11) 0.0415(10) 0.0422(12) -0.0090(8) 0.0055(8) -0.0015(8)
C7 0.0473(12) 0.0468(11) 0.0445(12) -0.0021(9) 0.0086(9) -0.0108(9)
C11 0.0446(12) 0.0662(13) 0.0534(14) -0.0118(10) 0.0044(10) 0.0083(10)
C5 0.0511(12) 0.0450(11) 0.0522(13) 0.0020(10) 0.0053(10) 0.0008(9)
C15 0.0411(11) 0.0567(12) 0.0479(13) -0.0021(10) 0.0022(9) 0.0040(9)
C4 0.0518(13) 0.0520(12) 0.0740(17) -0.0195(12) 0.0094(11) 0.0022(10)
C8 0.0405(11) 0.0780(14) 0.0466(13) -0.0080(11) 0.0037(9) 0.0011(10)
C1 0.0583(13) 0.0522(11) 0.0488(13) 0.0083(10) 0.0146(10) 0.0052(9)
C14 0.0521(13) 0.0789(15) 0.0466(13) 0.0036(11) 0.0037(10) 0.0006(11)
C3 0.0491(13) 0.0891(18) 0.0532(16) -0.0257(13) 0.0027(10) 0.0123(12)
C2 0.0644(15) 0.0877(18) 0.0402(14) 0.0043(12) 0.0085(10) 0.0152(12)
C13 0.0559(15) 0.0744(15) 0.0585(16) 0.0107(12) -0.0055(11) 0.0091(11)
C18 0.0488(13) 0.0930(17) 0.0563(15) 0.0009(12) -0.0032(10) -0.0046(12)
C12 0.0505(14) 0.0777(15) 0.0680(17) -0.0049(13) -0.0034(12) 0.0192(11)

_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 C17 1.341(2) . ?
O1 C18 1.436(2) . ?
N1 C9 1.274(2) . ?
N1 C16 1.461(2) . ?
C17 O2 1.201(2) . ?
C17 C16 1.497(3) . ?
C16 C7 1.582(3) . ?
C16 H16 0.9800 . ?
C6 C1 1.382(2) . ?
C6 C5 1.391(2) . ?
C6 C7 1.509(2) . ?
C10 C15 1.385(3) . ?
C10 C11 1.388(2) . ?
C10 C9 1.474(2) . ?
C9 C8 1.499(3) . ?
C7 C8 1.530(3) . ?
C7 H7 0.9800 . ?
C11 C12 1.385(3) . ?
C11 H11 0.9300 . ?
C5 C4 1.383(3) . ?
C5 H5 0.9300 . ?
C15 C14 1.383(3) . ?
C15 H15 0.9300 . ?
C4 C3 1.371(3) . ?
C4 H4 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C1 C2 1.379(3) . ?
C1 H1 0.9300 . ?
C14 C13 1.379(3) . ?
C14 H14 0.9300 . ?
C3 C2 1.366(3) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C13 C12 1.366(3) . ?
C13 H13 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C12 H12 0.9300 . ?

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
C17 O1 C18 117.86(15) . . ?
C9 N1 C16 110.28(15) . . ?
O2 C17 O1 123.53(18) . . ?
O2 C17 C16 126.36(17) . . ?
O1 C17 C16 110.08(16) . . ?
N1 C16 C17 111.10(15) . . ?
N1 C16 C7 107.39(15) . . ?
C17 C16 C7 113.53(15) . . ?
N1 C16 H16 108.2 . . ?
C17 C16 H16 108.2 . . ?
C7 C16 H16 108.2 . . ?
C1 C6 C5 117.46(18) . . ?
C1 C6 C7 120.38(17) . . ?
C5 C6 C7 122.14(17) . . ?
C15 C10 C11 118.18(18) . . ?
C15 C10 C9 120.92(16) . . ?
C11 C10 C9 120.89(17) . . ?
N1 C9 C10 122.47(16) . . ?
N1 C9 C8 115.37(17) . . ?
C10 C9 C8 122.17(16) . . ?
C6 C7 C8 115.25(15) . . ?
C6 C7 C16 116.01(15) . . ?
C8 C7 C16 102.21(15) . . ?
C6 C7 H7 107.6 . . ?
C8 C7 H7 107.6 . . ?
C16 C7 H7 107.6 . . ?
C12 C11 C10 120.4(2) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C4 C5 C6 120.7(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C14 C15 C10 121.14(18) . . ?
C14 C15 H15 119.4 . . ?
C10 C15 H15 119.4 . . ?
C3 C4 C5 120.6(2) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C9 C8 C7 104.60(15) . . ?
C9 C8 H8A 110.8 . . ?
C7 C8 H8A 110.8 . . ?
C9 C8 H8B 110.8 . . ?
C7 C8 H8B 110.8 . . ?
H8A C8 H8B 108.9 . . ?
C2 C1 C6 121.6(2) . . ?
C2 C1 H1 119.2 . . ?
C6 C1 H1 119.2 . . ?
C13 C14 C15 120.0(2) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C2 C3 C4 119.4(2) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C12 C13 C14 119.5(2) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
O1 C18 H18A 109.5 . . ?
O1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C13 C12 C11 120.9(2) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?

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
C18 O1 C17 O2 10.4(3) . . . . ?
C18 O1 C17 C16 -167.49(16) . . . . ?
C9 N1 C16 C17 -122.00(16) . . . . ?
C9 N1 C16 C7 2.69(19) . . . . ?
O2 C17 C16 N1 17.1(3) . . . . ?
O1 C17 C16 N1 -165.09(14) . . . . ?
O2 C17 C16 C7 -104.0(2) . . . . ?
O1 C17 C16 C7 73.76(18) . . . . ?
C16 N1 C9 C10 -179.86(15) . . . . ?
C16 N1 C9 C8 -0.2(2) . . . . ?
C15 C10 C9 N1 2.9(3) . . . . ?
C11 C10 C9 N1 -176.47(17) . . . . ?
C15 C10 C9 C8 -176.76(17) . . . . ?
C11 C10 C9 C8 3.9(3) . . . . ?
C1 C6 C7 C8 136.66(18) . . . . ?
C5 C6 C7 C8 -44.9(2) . . . . ?
C1 C6 C7 C16 -103.98(19) . . . . ?
C5 C6 C7 C16 74.4(2) . . . . ?
N1 C16 C7 C6 -130.15(16) . . . . ?
C17 C16 C7 C6 -6.9(2) . . . . ?
N1 C16 C7 C8 -3.91(18) . . . . ?
C17 C16 C7 C8 119.30(17) . . . . ?
C15 C10 C11 C12 -0.6(3) . . . . ?
C9 C10 C11 C12 178.77(18) . . . . ?
C1 C6 C5 C4 0.5(3) . . . . ?
C7 C6 C5 C4 -177.92(17) . . . . ?
C11 C10 C15 C14 0.2(3) . . . . ?
C9 C10 C15 C14 -179.15(17) . . . . ?
C6 C5 C4 C3 0.0(3) . . . . ?
N1 C9 C8 C7 -2.5(2) . . . . ?
C10 C9 C8 C7 177.23(15) . . . . ?
C6 C7 C8 C9 130.38(16) . . . . ?
C16 C7 C8 C9 3.65(18) . . . . ?
C5 C6 C1 C2 -0.9(3) . . . . ?
C7 C6 C1 C2 177.57(18) . . . . ?
C10 C15 C14 C13 0.5(3) . . . . ?
C5 C4 C3 C2 -0.1(3) . . . . ?
C4 C3 C2 C1 -0.3(3) . . . . ?
C6 C1 C2 C3 0.8(3) . . . . ?
C15 C14 C13 C12 -0.8(3) . . . . ?
C14 C13 C12 C11 0.4(3) . . . . ?
C10 C11 C12 C13 0.3(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.033