##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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.                                        #
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# 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 2.1.    #
#                                                                            #
# 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_global
_audit_creation_method     CrystalStructure_ver_3.5.1
_journal_date_recd_electronic     2007-03-26
_journal_date_accepted     2007-04-10
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      5
_journal_page_first     o2476
_journal_page_last     o2477
_journal_paper_category     EO
_journal_coeditor_code     CI2341
_publ_contact_author_name     'Jasinski, Jerry P.'
_publ_contact_author_address
;
 Department of Chemistry
 Keene State College
 229 Main Street
 Keene, NH 03435-2001 USA
;
_publ_contact_author_email     jjasinski@keene.edu
_publ_contact_author_fax     '603 358 2897'
_publ_contact_author_phone     '603 358 2563'
_publ_section_title
;
1-(2-Bromo-1-methyl-1H-indol-3-ylcarbonyl)piperidine
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Fraser, Heidi L. '
;
?
;
;
  Department of Chemistry
  Dartmouth College
  Hanover, NH 03755-3564, USA
;
    'Badenock, Jeanese C. '
;
?
;
;
  Department of Chemistry
  Dartmouth College
  Hanover, NH 03755-3564, USA
;
    'Gribble, Gordon W.'
;
?
;
;
  Department of Chemistry
  Dartmouth College
  Hanover, NH 03755-3564, USA
;
    'Jasinski, Jerry P.' .
;
  Department of Chemistry
  Keene State College
  Keene, NH 03435-2001, USA
;
data_I
_chemical_name_systematic
;
1-(2-Bromo-1-methylindol-3-ylcarbonyl)piperidine
;
_chemical_name_common     ?
_chemical_formula_moiety     'C15 H17 Br N2 O'
_chemical_formula_sum     'C15 H17 Br N2 O'
_chemical_formula_iupac     'C15 H17 Br N2 O'
_chemical_formula_weight     321.22
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     7.819(3)
_cell_length_b     8.218(3)
_cell_length_c     11.114(5)
_cell_angle_alpha     69.99(3)
_cell_angle_beta     91.21(4)
_cell_angle_gamma     111.16(3)
_cell_volume     621.5(4)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     8
_cell_measurement_theta_min     6.20
_cell_measurement_theta_max     11.97
_cell_measurement_temperature     296
_exptl_crystal_description     Prism
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.50
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.30
_exptl_crystal_density_diffrn     1.717
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     328
_exptl_absorpt_coefficient_mu     3.300
_exptl_absorpt_correction_type     psi-scan
_exptl_absorpt_process_details     '(North et al.,  1968)'
_exptl_absorpt_correction_T_min     0.2892
_exptl_absorpt_correction_T_max     0.4376
_exptl_special_details
;
¹H-NMR (CDCl₃)
δ 7.46-7.49 (m, 1H), 7.07-7.26 (m, 3H), 3.73 (bs, 5H), 1.59 (m, 8H);
 ¹³C-NMR (500 MHz, CDCl₃, -50°C) δ 164.5, 135.6, 125.0,
122.1, 120.6, 118.6, 113.9, 110.7, 109.5, 48.2, 42.7, 31.4, 26.6,
25.4, 24.1.
;
_diffrn_ambient_temperature     296
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_source     'normal-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Rigaku AFC-6S'
_diffrn_measurement_method     ω/2θ
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     2370
_diffrn_reflns_av_R_equivalents     0.0000
_diffrn_reflns_av_sigmaI/netI     0.2523
_diffrn_reflns_theta_min     1.96
_diffrn_reflns_theta_max     27.50
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.830
_diffrn_measured_fraction_theta_full     0.907
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     14
_diffrn_standards_number     3
_diffrn_standards_interval_count     150
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     -4.3
_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.
;
_reflns_number_total     2370
_reflns_number_gt     750
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.2707
_refine_ls_R_factor_gt     0.0606
_refine_ls_wR_factor_gt     0.1566
_refine_ls_wR_factor_ref     0.2450
_refine_ls_goodness_of_fit_ref     0.945
_refine_ls_restrained_S_all     0.945
_refine_ls_number_reflns     2370
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.1228P)²] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.474
_refine_diff_density_min     -0.907
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
    'O' 'O' 0.0106 0.0060
                         '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'
    'Br' 'Br' -0.2901 2.4595
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1994)'
;
_computing_cell_refinement     'MSC/AFC Diffractometer Control Software'
_computing_data_reduction     'CrystalStructure (Rigaku/MSC, 2005)'
_computing_structure_solution     'SIR92 (Altomare et al.,  1994)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material     'CrystalStructure'
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
    Br Br1 1.0355(2) 0.2788(2) 1.05707(13) 0.0744(7) Uani d . 1 . .
    O O1 1.1437(13) 0.4727(11) 0.7357(8) 0.070(2) Uani d . 1 . .
    N N1 0.7622(13) 0.0009(14) 1.0107(10) 0.054(2) Uani d . 1 . .
    N N2 0.9076(13) 0.5477(14) 0.6866(9) 0.058(3) Uani d . 1 . .
    C C2 0.8793(16) 0.1756(17) 0.9583(11) 0.051(3) Uani d . 1 . .
    C C3 0.8640(15) 0.2512(18) 0.8363(11) 0.051(3) Uani d . 1 . .
    C C4 0.7300(16) 0.1130(17) 0.8096(13) 0.052(3) Uani d . 1 . .
    C C5 0.6518(18) 0.1029(19) 0.7008(12) 0.060(3) Uani d . 1 . .
    H H1 0.6885 0.2061 0.6244 0.073 Uiso calc R 1 . .
    C C6 0.5241(19) -0.055(2) 0.7059(14) 0.066(3) Uani d . 1 . .
    H H2 0.4734 -0.0629 0.6306 0.079 Uiso calc R 1 . .
    C C7 0.4624(18) -0.205(2) 0.814(2) 0.079(4) Uani d . 1 . .
    H H3 0.3693 -0.3145 0.8133 0.095 Uiso calc R 1 . .
    C C8 0.5366(18) -0.198(2) 0.9239(13) 0.065(3) Uani d . 1 . .
    H H4 0.4974 -0.3014 1.0003 0.078 Uiso calc R 1 . .
    C C9 0.6669(17) -0.0386(18) 0.9189(15) 0.059(3) Uani d . 1 . .
    C C10 0.7359(18) -0.1226(16) 1.1413(11) 0.072(4) Uani d . 1 . .
    H H5 0.8169 -0.1895 1.1519 0.086 Uiso calc R 1 . .
    H H6 0.6101 -0.2097 1.1629 0.086 Uiso calc R 1 . .
    H H7 0.7629 -0.0516 1.1971 0.086 Uiso calc R 1 . .
    C C11 0.984(2) 0.4319(16) 0.7529(11) 0.055(3) Uani d . 1 . .
    C C12 1.0136(16) 0.7211(15) 0.5986(11) 0.062(3) Uani d . 1 . .
    H H8 1.1334 0.7226 0.5761 0.074 Uiso calc R 1 . .
    H H9 1.0324 0.8158 0.6363 0.074 Uiso calc R 1 . .
    C C13 0.9209(18) 0.7624(18) 0.4831(11) 0.068(3) Uani d . 1 . .
    H H10 0.9118 0.6741 0.4412 0.081 Uiso calc R 1 . .
    H H11 0.9921 0.8871 0.4231 0.081 Uiso calc R 1 . .
    C C14 0.7349(18) 0.7499(17) 0.5181(12) 0.068(4) Uani d . 1 . .
    H H12 0.7447 0.8467 0.5521 0.082 Uiso calc R 1 . .
    H H13 0.6710 0.7701 0.4418 0.082 Uiso calc R 1 . .
    C C15 0.6307(17) 0.5697(18) 0.6131(12) 0.072(4) Uani d . 1 . .
    H H14 0.6091 0.4745 0.5754 0.086 Uiso calc R 1 . .
    H H15 0.5117 0.5671 0.6388 0.086 Uiso calc R 1 . .
    C C16 0.7277(16) 0.5265(16) 0.7278(11) 0.059(3) Uani d . 1 . .
    H H16 0.7355 0.6108 0.7729 0.071 Uiso calc R 1 . .
    H H17 0.6610 0.3994 0.7861 0.071 Uiso calc R 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
    Br1 0.0853(11) 0.0846(11) 0.0695(10) 0.0413(8) -0.0240(7) -0.0377(8)
    O1 0.057(6) 0.054(5) 0.088(6) 0.013(5) -0.003(5) -0.019(5)
    N1 0.048(6) 0.048(7) 0.069(7) 0.019(6) -0.011(6) -0.026(6)
    N2 0.046(7) 0.056(7) 0.055(6) 0.017(6) 0.006(5) -0.003(6)
    C2 0.053(7) 0.053(8) 0.062(9) 0.010(7) -0.029(7) -0.051(8)
    C3 0.044(7) 0.071(10) 0.054(8) 0.025(7) -0.019(6) -0.038(8)
    C4 0.050(8) 0.047(8) 0.064(9) 0.022(7) -0.001(7) -0.022(8)
    C5 0.064(9) 0.060(9) 0.062(9) 0.019(8) -0.008(7) -0.033(7)
    C6 0.066(9) 0.070(10) 0.073(10) 0.028(8) -0.022(8) -0.037(9)
    C7 0.055(9) 0.057(10) 0.133(14) 0.015(8) -0.005(10) -0.049(11)
    C8 0.059(9) 0.068(10) 0.076(10) 0.027(8) 0.009(8) -0.030(8)
    C9 0.050(8) 0.038(8) 0.094(11) 0.009(7) -0.001(8) -0.039(9)
    C10 0.096(10) 0.060(8) 0.052(8) 0.037(8) 0.006(7) -0.003(7)
    C11 0.056(9) 0.045(9) 0.051(8) 0.001(8) 0.001(8) -0.022(7)
    C12 0.061(8) 0.039(8) 0.063(8) 0.008(7) 0.009(7) -0.003(7)
    C13 0.080(10) 0.066(8) 0.047(8) 0.025(7) -0.006(7) -0.009(7)
    C14 0.075(10) 0.064(9) 0.056(8) 0.023(8) -0.018(7) -0.015(7)
    C15 0.061(8) 0.072(10) 0.070(9) 0.020(7) 0.000(8) -0.016(8)
    C16 0.056(9) 0.052(8) 0.057(8) 0.014(6) -0.011(7) -0.013(6)
_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Br1 C2 . 1.803(9) ?
    O1 C11 . 1.170(13) ?
    N1 C9 . 1.312(15) ?
    N1 C2 . 1.319(14) ?
    N1 C10 . 1.426(14) ?
    N2 C11 . 1.312(14) ?
    N2 C12 . 1.379(14) ?
    N2 C16 . 1.419(14) ?
    C2 C3 . 1.307(15) ?
    C3 C4 . 1.354(16) ?
    C3 C11 . 1.427(16) ?
    C4 C9 . 1.349(16) ?
    C4 C5 . 1.358(15) ?
    C5 C6 . 1.303(16) ?
    C5 H1 . 0.93 ?
    C6 C7 . 1.334(18) ?
    C6 H2 . 0.93 ?
    C7 C8 . 1.355(18) ?
    C7 H3 . 0.93 ?
    C8 C9 . 1.321(17) ?
    C8 H4 . 0.93 ?
    C10 H5 . 0.96 ?
    C10 H6 . 0.96 ?
    C10 H7 . 0.96 ?
    C12 C13 . 1.459(15) ?
    C12 H8 . 0.97 ?
    C12 H9 . 0.97 ?
    C13 C14 . 1.472(16) ?
    C13 H10 . 0.97 ?
    C13 H11 . 0.97 ?
    C14 C15 . 1.438(16) ?
    C14 H12 . 0.97 ?
    C14 H13 . 0.97 ?
    C15 C16 . 1.473(16) ?
    C15 H14 . 0.97 ?
    C15 H15 . 0.97 ?
    C16 H16 . 0.97 ?
    C16 H17 . 0.97 ?
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
    C9 N1 C2 . . 106.3(10) ?
    C9 N1 C10 . . 125.4(11) ?
    C2 N1 C10 . . 128.3(11) ?
    C11 N2 C12 . . 120.8(10) ?
    C11 N2 C16 . . 121.1(10) ?
    C12 N2 C16 . . 115.5(10) ?
    C3 C2 N1 . . 112.7(10) ?
    C3 C2 Br1 . . 128.5(11) ?
    N1 C2 Br1 . . 118.8(9) ?
    C2 C3 C4 . . 104.4(12) ?
    C2 C3 C11 . . 124.6(11) ?
    C4 C3 C11 . . 130.5(11) ?
    C9 C4 C3 . . 108.4(12) ?
    C9 C4 C5 . . 118.3(12) ?
    C3 C4 C5 . . 133.2(13) ?
    C6 C5 C4 . . 118.5(12) ?
    C6 C5 H1 . . 120.8 ?
    C4 C5 H1 . . 120.8 ?
    C5 C6 C7 . . 123.2(14) ?
    C5 C6 H2 . . 118.4 ?
    C7 C6 H2 . . 118.4 ?
    C6 C7 C8 . . 119.4(12) ?
    C6 C7 H3 . . 120.3 ?
    C8 C7 H3 . . 120.3 ?
    C9 C8 C7 . . 117.5(14) ?
    C9 C8 H4 . . 121.2 ?
    C7 C8 H4 . . 121.2 ?
    N1 C9 C8 . . 128.8(15) ?
    N1 C9 C4 . . 108.2(11) ?
    C8 C9 C4 . . 123.0(14) ?
    N1 C10 H5 . . 109.5 ?
    N1 C10 H6 . . 109.5 ?
    H5 C10 H6 . . 109.5 ?
    N1 C10 H7 . . 109.5 ?
    H5 C10 H7 . . 109.5 ?
    H6 C10 H7 . . 109.5 ?
    O1 C11 N2 . . 120.3(11) ?
    O1 C11 C3 . . 122.2(13) ?
    N2 C11 C3 . . 117.3(12) ?
    N2 C12 C13 . . 109.7(10) ?
    N2 C12 H8 . . 109.7 ?
    C13 C12 H8 . . 109.7 ?
    N2 C12 H9 . . 109.7 ?
    C13 C12 H9 . . 109.7 ?
    H8 C12 H9 . . 108.2 ?
    C12 C13 C14 . . 109.8(10) ?
    C12 C13 H10 . . 109.7 ?
    C14 C13 H10 . . 109.7 ?
    C12 C13 H11 . . 109.7 ?
    C14 C13 H11 . . 109.7 ?
    H10 C13 H11 . . 108.2 ?
    C15 C14 C13 . . 110.6(11) ?
    C15 C14 H12 . . 109.5 ?
    C13 C14 H12 . . 109.5 ?
    C15 C14 H13 . . 109.5 ?
    C13 C14 H13 . . 109.5 ?
    H12 C14 H13 . . 108.1 ?
    C14 C15 C16 . . 111.8(11) ?
    C14 C15 H14 . . 109.3 ?
    C16 C15 H14 . . 109.3 ?
    C14 C15 H15 . . 109.3 ?
    C16 C15 H15 . . 109.3 ?
    H14 C15 H15 . . 107.9 ?
    N2 C16 C15 . . 108.3(10) ?
    N2 C16 H16 . . 110.0 ?
    C15 C16 H16 . . 110.0 ?
    N2 C16 H17 . . 110.0 ?
    C15 C16 H17 . . 110.0 ?
    H16 C16 H17 . . 108.4 ?
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
    C7 H3 O1 1_445 0.93 2.38 3.27(2) 160
    C10 H5 O1 2_757 0.96 2.36 3.200(17) 145
    C16 H16 Br1 2_767 0.97 2.73 3.464(13) 133
