##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Methyl 2-(1H-indole-3-carboxamido)acetate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C12 H12 N2 O3'
_chemical_formula_sum     'C12 H12 N2 O3'
_chemical_formula_iupac     'C12 H12 N2 O3'
_chemical_formula_weight     232.24
_chemical_melting_point     448
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
_symmetry_space_group_name_Hall     'P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
_cell_length_a     8.0024(2)
_cell_length_b     9.1279(2)
_cell_length_c     15.9767(3)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1167.02(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1985
_cell_measurement_theta_min     4.8408
_cell_measurement_theta_max     62.6295
_cell_measurement_temperature     150(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     'light yellow'
_exptl_crystal_size_max     0.49
_exptl_crystal_size_mid     0.17
_exptl_crystal_size_min     0.12
_exptl_crystal_density_diffrn     1.322
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     488
_exptl_absorpt_coefficient_mu     0.804
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(CrysAlis PRO; Oxford Diffraction, 2010)'
_exptl_absorpt_correction_T_min     0.6942
_exptl_absorpt_correction_T_max     0.9097
_exptl_special_details
;
;
_diffrn_ambient_temperature     150(2)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     mirror
_diffrn_measurement_device_type     'Oxford Gemini S Ultra area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     .
_diffrn_reflns_number     2269
_diffrn_reflns_av_R_equivalents     0.0156
_diffrn_reflns_av_sigmaI/netI     0.0231
_diffrn_reflns_theta_min     5.58
_diffrn_reflns_theta_max     62.72
_diffrn_reflns_theta_full     62.72
_diffrn_measured_fraction_theta_max     0.971
_diffrn_measured_fraction_theta_full     0.971
_diffrn_reflns_limit_h_min     -5
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_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 >
σ(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.
;
_reflns_number_total     1642
_reflns_number_gt     1613
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0296
_refine_ls_R_factor_gt     0.0291
_refine_ls_wR_factor_gt     0.0765
_refine_ls_wR_factor_ref     0.0771
_refine_ls_goodness_of_fit_ref     1.046
_refine_ls_restrained_S_all     1.046
_refine_ls_number_reflns     1642
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0478P)²+0.0803P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.011
_refine_ls_shift/su_mean     0.001
_refine_diff_density_max     0.125
_refine_diff_density_min     -0.139
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     'Flack (1983), 568 Friedel pairs'
_refine_ls_abs_structure_Flack     -0.2(3)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0181 0.0091
                         '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' 0.0311 0.0180
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0492 0.0322
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_cell_refinement     'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_reduction     'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.8259(2) 0.08538(18) 0.12627(10) 0.0418(4) Uani d . 1 . .
    H H1 0.9222 0.0261 0.1184 0.050 Uiso calc R 1 . .
    N N1 0.68538(19) 0.07824(16) 0.07961(9) 0.0491(4) Uani d . 1 . .
    H H1A 0.6691 0.0180 0.0374 0.059 Uiso calc R 1 . .
    C C8 0.5711(2) 0.17992(19) 0.10821(10) 0.0451(4) Uani d . 1 . .
    C C3 0.6450(2) 0.25391(16) 0.17586(9) 0.0400(4) Uani d . 1 . .
    C C4 0.5524(2) 0.36258(18) 0.21720(11) 0.0498(4) Uani d . 1 . .
    H H4 0.5985 0.4145 0.2633 0.060 Uiso calc R 1 . .
    C C5 0.3925(3) 0.3921(2) 0.18931(12) 0.0608(5) Uani d . 1 . .
    H H5 0.3288 0.4657 0.2167 0.073 Uiso calc R 1 . .
    C C6 0.3219(3) 0.3166(3) 0.12172(14) 0.0660(6) Uani d . 1 . .
    H H6 0.2115 0.3397 0.1044 0.079 Uiso calc R 1 . .
    C C7 0.4094(3) 0.2099(2) 0.08007(12) 0.0593(5) Uani d . 1 . .
    H H7 0.3621 0.1586 0.0341 0.071 Uiso calc R 1 . .
    C C9 0.9272(2) 0.22893(16) 0.25277(10) 0.0383(4) Uani d . 1 . .
    C C10 1.1689(2) 0.1685(2) 0.33471(10) 0.0432(4) Uani d . 1 . .
    H H10A 1.2129 0.2687 0.3260 0.052 Uiso calc R 1 . .
    H H10B 1.2642 0.0995 0.3315 0.052 Uiso calc R 1 . .
    C C11 1.0915(2) 0.15897(18) 0.42041(10) 0.0394(4) Uani d . 1 . .
    C C12 1.1129(3) 0.2444(3) 0.55958(11) 0.0767(7) Uani d . 1 . .
    H H12A 1.1425 0.1492 0.5839 0.115 Uiso calc R 1 . .
    H H12B 0.9915 0.2577 0.5621 0.115 Uiso calc R 1 . .
    H H12C 1.1680 0.3226 0.5912 0.115 Uiso calc R 1 . .
    C C2 0.8088(2) 0.19136(16) 0.18683(10) 0.0380(4) Uani d . 1 . .
    N N2 1.05189(17) 0.13476(14) 0.26902(8) 0.0419(3) Uani d . 1 . .
    H H2 1.0620 0.0534 0.2399 0.050 Uiso calc R 1 . .
    O O1 0.91340(16) 0.34378(12) 0.29446(7) 0.0476(3) Uani d . 1 . .
    O O2 0.97901(16) 0.07845(14) 0.43919(8) 0.0561(4) Uani d . 1 . .
    O O3 1.16709(15) 0.24943(15) 0.47336(7) 0.0549(4) Uani d . 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    C1 0.0480(9) 0.0397(8) 0.0377(8) 0.0024(8) -0.0025(8) -0.0015(7)
    N1 0.0594(9) 0.0479(8) 0.0401(7) 0.0050(8) -0.0094(7) -0.0091(7)
    C8 0.0508(10) 0.0442(9) 0.0404(9) 0.0019(8) -0.0013(8) 0.0033(8)
    C3 0.0511(9) 0.0351(8) 0.0339(7) 0.0003(7) 0.0034(8) 0.0053(7)
    C4 0.0644(11) 0.0433(8) 0.0417(9) 0.0059(9) 0.0127(9) 0.0024(8)
    C5 0.0680(12) 0.0583(11) 0.0561(11) 0.0205(10) 0.0158(11) 0.0109(9)
    C6 0.0540(11) 0.0778(14) 0.0662(13) 0.0175(11) 0.0044(11) 0.0201(12)
    C7 0.0564(11) 0.0669(12) 0.0546(11) 0.0039(11) -0.0117(10) 0.0074(10)
    C9 0.0491(9) 0.0338(7) 0.0319(7) -0.0079(7) 0.0056(7) 0.0023(7)
    C10 0.0386(8) 0.0511(9) 0.0398(8) -0.0043(8) 0.0017(8) -0.0026(8)
    C11 0.0371(8) 0.0409(8) 0.0403(9) -0.0010(8) -0.0037(7) 0.0024(7)
    C12 0.0694(13) 0.1237(19) 0.0370(9) -0.0244(14) 0.0026(10) -0.0143(12)
    C2 0.0483(9) 0.0319(8) 0.0337(8) -0.0024(7) 0.0030(7) 0.0011(6)
    N2 0.0491(8) 0.0394(6) 0.0372(7) -0.0002(6) 0.0000(6) -0.0061(6)
    O1 0.0636(7) 0.0346(5) 0.0446(6) -0.0035(6) -0.0024(6) -0.0080(5)
    O2 0.0574(7) 0.0629(7) 0.0481(7) -0.0217(7) 0.0045(6) 0.0062(6)
    O3 0.0528(7) 0.0742(8) 0.0376(6) -0.0197(7) -0.0002(6) -0.0072(7)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 N1 . 1.351(2) ?
    C1 C2 . 1.375(2) ?
    C1 H1 . 0.9500 ?
    N1 C8 . 1.381(2) ?
    N1 H1A . 0.8800 ?
    C8 C7 . 1.397(3) ?
    C8 C3 . 1.405(2) ?
    C3 C4 . 1.403(2) ?
    C3 C2 . 1.440(2) ?
    C4 C5 . 1.381(3) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.400(3) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.372(3) ?
    C6 H6 . 0.9500 ?
    C7 H7 . 0.9500 ?
    C9 O1 . 1.2470(19) ?
    C9 N2 . 1.342(2) ?
    C9 C2 . 1.458(2) ?
    C10 N2 . 1.440(2) ?
    C10 C11 . 1.505(2) ?
    C10 H10A . 0.9900 ?
    C10 H10B . 0.9900 ?
    C11 O2 . 1.2002(19) ?
    C11 O3 . 1.328(2) ?
    C12 O3 . 1.445(2) ?
    C12 H12A . 0.9800 ?
    C12 H12B . 0.9800 ?
    C12 H12C . 0.9800 ?
    N2 H2 . 0.8800 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    N1 C1 C2 . . 109.84(15) ?
    N1 C1 H1 . . 125.1 ?
    C2 C1 H1 . . 125.1 ?
    C1 N1 C8 . . 109.64(14) ?
    C1 N1 H1A . . 125.2 ?
    C8 N1 H1A . . 125.2 ?
    N1 C8 C7 . . 129.68(17) ?
    N1 C8 C3 . . 107.41(15) ?
    C7 C8 C3 . . 122.90(17) ?
    C4 C3 C8 . . 118.67(16) ?
    C4 C3 C2 . . 134.70(16) ?
    C8 C3 C2 . . 106.61(14) ?
    C5 C4 C3 . . 118.38(18) ?
    C5 C4 H4 . . 120.8 ?
    C3 C4 H4 . . 120.8 ?
    C4 C5 C6 . . 121.75(18) ?
    C4 C5 H5 . . 119.1 ?
    C6 C5 H5 . . 119.1 ?
    C7 C6 C5 . . 121.2(2) ?
    C7 C6 H6 . . 119.4 ?
    C5 C6 H6 . . 119.4 ?
    C6 C7 C8 . . 117.10(19) ?
    C6 C7 H7 . . 121.4 ?
    C8 C7 H7 . . 121.4 ?
    O1 C9 N2 . . 120.08(15) ?
    O1 C9 C2 . . 121.73(15) ?
    N2 C9 C2 . . 118.18(13) ?
    N2 C10 C11 . . 112.53(13) ?
    N2 C10 H10A . . 109.1 ?
    C11 C10 H10A . . 109.1 ?
    N2 C10 H10B . . 109.1 ?
    C11 C10 H10B . . 109.1 ?
    H10A C10 H10B . . 107.8 ?
    O2 C11 O3 . . 124.28(16) ?
    O2 C11 C10 . . 124.84(15) ?
    O3 C11 C10 . . 110.86(14) ?
    O3 C12 H12A . . 109.5 ?
    O3 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    O3 C12 H12C . . 109.5 ?
    H12A C12 H12C . . 109.5 ?
    H12B C12 H12C . . 109.5 ?
    C1 C2 C3 . . 106.50(14) ?
    C1 C2 C9 . . 127.52(15) ?
    C3 C2 C9 . . 125.89(14) ?
    C9 N2 C10 . . 119.16(13) ?
    C9 N2 H2 . . 120.4 ?
    C10 N2 H2 . . 120.4 ?
    C11 O3 C12 . . 116.79(14) ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C2 C1 N1 C8 . . . . 0.05(19) ?
    C1 N1 C8 C7 . . . . -178.97(19) ?
    C1 N1 C8 C3 . . . . 0.15(19) ?
    N1 C8 C3 C4 . . . . -179.08(14) ?
    C7 C8 C3 C4 . . . . 0.1(3) ?
    N1 C8 C3 C2 . . . . -0.28(18) ?
    C7 C8 C3 C2 . . . . 178.92(16) ?
    C8 C3 C4 C5 . . . . -0.1(2) ?
    C2 C3 C4 C5 . . . . -178.51(18) ?
    C3 C4 C5 C6 . . . . 0.2(3) ?
    C4 C5 C6 C7 . . . . -0.2(3) ?
    C5 C6 C7 C8 . . . . 0.2(3) ?
    N1 C8 C7 C6 . . . . 178.87(18) ?
    C3 C8 C7 C6 . . . . -0.1(3) ?
    N2 C10 C11 O2 . . . . 30.2(2) ?
    N2 C10 C11 O3 . . . . -151.31(14) ?
    N1 C1 C2 C3 . . . . -0.22(18) ?
    N1 C1 C2 C9 . . . . 176.50(15) ?
    C4 C3 C2 C1 . . . . 178.82(17) ?
    C8 C3 C2 C1 . . . . 0.30(17) ?
    C4 C3 C2 C9 . . . . 2.0(3) ?
    C8 C3 C2 C9 . . . . -176.48(14) ?
    O1 C9 C2 C1 . . . . 166.46(15) ?
    N2 C9 C2 C1 . . . . -14.7(2) ?
    O1 C9 C2 C3 . . . . -17.4(2) ?
    N2 C9 C2 C3 . . . . 161.42(15) ?
    O1 C9 N2 C10 . . . . -0.2(2) ?
    C2 C9 N2 C10 . . . . -179.07(14) ?
    C11 C10 N2 C9 . . . . 69.72(19) ?
    O2 C11 O3 C12 . . . . 2.6(3) ?
    C10 C11 O3 C12 . . . . -175.89(17) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    N2 H2 O1 3_745 0.88 2.00 2.8566(17) 164
    N1 H1A O2 2_654 0.88 2.15 2.9680(18) 154
data_global
_journal_date_recd_electronic     2011-02-05
_journal_date_accepted     2011-02-22
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue      3
_journal_page_first     o742
_journal_page_last     o742
_journal_paper_category     QO
_journal_coeditor_code     RZ2556
_publ_contact_author_name     'Xiang Chao Zeng'
_publ_contact_author_address
;Department of Chemistry,
Jinan University,
Guangzhou,
Guangdong, 510632,
People's Republic of China
;
_publ_contact_author_email     xczeng@126.com
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
Methyl 2-(1H-indole-3-carboxamido)acetate
;
loop_
    _publ_author_name
    _publ_author_address
    'Hu, Fang'
;
Department of Chemistry,
Jinan University,
Guangzhou,
Guangdong 510632,
People's Republic of China
;
    'Zheng, Le'
;
Department of Chemistry,
Jinan University,
Guangzhou,
Guangdong 510632,
People's Republic of China
;
    'Zeng, Xiang Chao'
;
Department of Chemistry,
Jinan University,
Guangzhou,
Guangdong 510632,
People's Republic of China
;
    'Li, Kai Ping'
;
Department of Chemistry,
Jinan University,
Guangzhou,
Guangdong 510632,
People's Republic of China
;
