##############################################################################
###                                                                        ###
###        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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# 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 2.1.    #
#                                                                            #
# 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.
_journal_date_recd_electronic     2007-03-27
_journal_date_accepted     2007-04-11
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      5
_journal_page_first     o2478
_journal_page_last     o2479
_journal_paper_category     EO
_journal_coeditor_code     CI2348
_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
;\
2-Bromo-N-tert-butyl-N,1-dimethyl-1H-indole-3-\
carboxamide
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Badenock, Jeanese C. '
;
?
;
;
  Department of Chemistry
  Dartmouth College
  Hanover, NH 03755-3564, USA
;
    'Fraser, Heidi L. '
;
?
;
;
  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
;
2-Bromo-N-tert-butyl-N,1-dimethyl-1H-indole-3-carboxamide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C15 H19 Br N2 O'
_chemical_formula_sum     'C15 H19 Br N2 O'
_chemical_formula_iupac     'C15 H19 Br N2 O'
_chemical_formula_weight     323.23
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     7.373(7)
_cell_length_b     21.453(7)
_cell_length_c     9.132(9)
_cell_angle_alpha     90.00
_cell_angle_beta     96.06(9)
_cell_angle_gamma     90.00
_cell_volume     1436(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     18
_cell_measurement_theta_min     6.26
_cell_measurement_theta_max     7.62
_cell_measurement_temperature     296(2)
_exptl_crystal_description     Plate
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.50
_exptl_crystal_size_mid     0.40
_exptl_crystal_size_min     0.30
_exptl_crystal_density_diffrn     1.495
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     664
_exptl_absorpt_coefficient_mu     2.856
_exptl_absorpt_correction_type     psi-scan
_exptl_absorpt_process_details     '(North et al.,  1968)'
_exptl_absorpt_correction_T_min     0.3293
_exptl_absorpt_correction_T_max     0.4812
_exptl_special_details
;
 ¹H-NMR (CDCl₃) δ 7.57-7.71 (dt, 1H, J = 1.2, 8.0 Hz), 7.14-7.34
(m, 3H), 3.76 (s, 3H), 2.96 (s, 3H), 1.57 (s, 9H); ¹³C-NMR (CDCl₃)
 δ 167.1, 136.4, 125.8, 122.5, 121.0, 119.6, 114.7, 114.2, 109.5, 56.5,
34.2, 31.5, 28.0; IR ν(film) 3456, 3052, 2979, 1627, 1516, 1466, 1386,
1386, 1332 1265 cm⁻¹; UV λₘₐₓ (95% EtOH) 212, 266, 290, 332,
 348 nm; GCMS m/z 323 (M⁺), 307, 268, 236 (100%), 208, 169, 158,
 129.  Anal. Calcd for C₁₅H₁₉BrN₂O: C, 55.74; H, 5.92; N,
8.67; Br, 24.72. Found: C, 56.13; H, 5.94; N, 8.64; Br, 24.42.
;
_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     2526
_diffrn_reflns_av_R_equivalents     0.0000
_diffrn_reflns_av_sigmaI/netI     0.1794
_diffrn_reflns_theta_min     2.44
_diffrn_reflns_theta_max     24.97
_diffrn_reflns_theta_full     24.97
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     25
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_limit_l_max     10
_diffrn_standards_number     3
_diffrn_standards_interval_count     150
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     -1.4
_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     2526
_reflns_number_gt     992
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.2065
_refine_ls_R_factor_gt     0.0509
_refine_ls_wR_factor_gt     0.1277
_refine_ls_wR_factor_ref     0.1747
_refine_ls_goodness_of_fit_ref     1.022
_refine_ls_restrained_S_all     1.022
_refine_ls_number_reflns     2526
_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)+(0.0537P)²+5.0079P] 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     0.511
_refine_diff_density_min     -0.447
_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 0.59300(16) 0.08595(5) 0.13479(11) 0.0571(4) Uani d . 1 . .
    O O1 0.5124(9) 0.1722(3) 0.5760(6) 0.0439(16) Uani d . 1 . .
    N N1 0.7113(9) 0.0016(3) 0.3574(8) 0.0378(18) Uani d . 1 . .
    C C13 0.5343(12) 0.2629(4) 0.3535(9) 0.033(2) Uani d . 1 . .
    C C2 0.6629(11) 0.0619(4) 0.3285(9) 0.030(2) Uani d . 1 . .
    C C3 0.6683(11) 0.0964(4) 0.4556(9) 0.031(2) Uani d . 1 . .
    C C4 0.7261(11) 0.0540(4) 0.5733(9) 0.031(2) Uani d . 1 . .
    C C5 0.7571(12) 0.0586(4) 0.7258(10) 0.041(2) Uani d . 1 . .
    H H1 0.7353 0.0958 0.7729 0.049 Uiso calc R 1 . .
    C C6 0.8203(13) 0.0074(5) 0.8060(11) 0.055(3) Uani d . 1 . .
    H H2 0.8452 0.0107 0.9077 0.066 Uiso calc R 1 . .
    C C7 0.8479(13) -0.0494(5) 0.7374(12) 0.052(3) Uani d . 1 . .
    H H4 0.8895 -0.0834 0.7943 0.062 Uiso calc R 1 . .
    C C8 0.8154(12) -0.0559(5) 0.5903(12) 0.051(3) Uani d . 1 . .
    H H3 0.8342 -0.0939 0.5455 0.062 Uiso calc R 1 . .
    C C9 0.7533(11) -0.0045(4) 0.5070(10) 0.035(2) Uani d . 1 . .
    C C10 0.7190(14) -0.0497(4) 0.2536(11) 0.054(3) Uani d . 1 . .
    H H5 0.6021 -0.0698 0.2390 0.065 Uiso calc R 1 . .
    H H6 0.8095 -0.0792 0.2922 0.065 Uiso calc R 1 . .
    H H7 0.7504 -0.0338 0.1613 0.065 Uiso calc R 1 . .
    C C11 0.6029(12) 0.1607(4) 0.4737(9) 0.036(2) Uani d . 1 . .
    N N2 0.6423(9) 0.2041(3) 0.3740(7) 0.0321(18) Uani d . 1 . .
    C C12 0.8187(12) 0.2027(4) 0.3152(11) 0.048(3) Uani d . 1 . .
    H H8 0.8027 0.1886 0.2149 0.057 Uiso calc R 1 . .
    H H9 0.8991 0.1748 0.3728 0.057 Uiso calc R 1 . .
    H H10 0.8703 0.2439 0.3191 0.057 Uiso calc R 1 . .
    C C14 0.5563(14) 0.2880(4) 0.1995(9) 0.043(2) Uani d . 1 . .
    H H11 0.6609 0.3148 0.2041 0.052 Uiso calc R 1 . .
    H H12 0.4492 0.3110 0.1634 0.052 Uiso calc R 1 . .
    H H13 0.5726 0.2538 0.1344 0.052 Uiso calc R 1 . .
    C C15 0.3310(12) 0.2491(5) 0.3560(9) 0.048(3) Uani d . 1 . .
    H H14 0.2768 0.2409 0.2577 0.057 Uiso calc R 1 . .
    H H15 0.2723 0.2843 0.3952 0.057 Uiso calc R 1 . .
    H H16 0.3165 0.2132 0.4167 0.057 Uiso calc R 1 . .
    C C16 0.5999(14) 0.3110(4) 0.4681(10) 0.049(3) Uani d . 1 . .
    H H17 0.5331 0.3066 0.5522 0.059 Uiso calc R 1 . .
    H H18 0.5807 0.3520 0.4273 0.059 Uiso calc R 1 . .
    H H19 0.7275 0.3049 0.4974 0.059 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 0.0740(8) 0.0584(7) 0.0389(5) -0.0039(7) 0.0058(4) -0.0025(6)
    O1 0.058(4) 0.044(4) 0.034(3) 0.003(3) 0.023(3) 0.002(3)
    N1 0.038(5) 0.030(5) 0.046(5) -0.007(4) 0.011(4) -0.008(4)
    C13 0.043(6) 0.029(5) 0.029(5) 0.004(5) 0.009(4) 0.007(4)
    C2 0.031(5) 0.022(5) 0.037(5) -0.005(4) 0.007(4) 0.007(4)
    C3 0.029(5) 0.028(5) 0.034(5) -0.002(4) 0.001(4) 0.002(4)
    C4 0.020(5) 0.029(5) 0.042(5) 0.003(4) 0.002(4) 0.001(4)
    C5 0.040(6) 0.037(6) 0.046(6) -0.003(5) 0.011(5) 0.005(5)
    C6 0.052(7) 0.071(8) 0.042(6) -0.012(6) 0.007(5) 0.023(6)
    C7 0.048(7) 0.036(7) 0.071(8) 0.005(5) 0.007(6) 0.020(6)
    C8 0.042(6) 0.042(6) 0.071(8) 0.006(5) 0.010(5) 0.017(6)
    C9 0.020(5) 0.037(6) 0.049(6) -0.002(4) 0.009(4) 0.006(5)
    C10 0.068(8) 0.029(6) 0.066(7) -0.002(5) 0.013(6) -0.011(5)
    C11 0.037(6) 0.035(6) 0.036(5) -0.003(5) 0.002(5) 0.003(4)
    N2 0.029(4) 0.031(4) 0.039(4) 0.004(4) 0.015(3) 0.003(3)
    C12 0.042(6) 0.041(6) 0.061(6) -0.007(5) 0.009(5) 0.007(5)
    C14 0.061(7) 0.023(5) 0.046(5) 0.004(5) 0.006(5) 0.003(4)
    C15 0.041(6) 0.055(6) 0.047(6) 0.013(5) 0.007(5) 0.016(5)
    C16 0.058(7) 0.038(6) 0.051(6) -0.001(5) 0.007(5) -0.003(5)
_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 . 1.862(8) ?
    O1 C11 . 1.230(9) ?
    N1 C2 . 1.361(10) ?
    N1 C9 . 1.375(11) ?
    N1 C10 . 1.456(10) ?
    C13 N2 . 1.493(10) ?
    C13 C16 . 1.512(12) ?
    C13 C15 . 1.530(12) ?
    C13 C14 . 1.530(11) ?
    C2 C3 . 1.374(11) ?
    C3 C4 . 1.437(11) ?
    C3 C11 . 1.476(12) ?
    C4 C5 . 1.391(11) ?
    C4 C9 . 1.417(12) ?
    C5 C6 . 1.374(13) ?
    C5 H1 . 0.93 ?
    C6 C7 . 1.394(14) ?
    C6 H2 . 0.93 ?
    C7 C8 . 1.346(13) ?
    C7 H4 . 0.93 ?
    C8 C9 . 1.388(12) ?
    C8 H3 . 0.93 ?
    C10 H5 . 0.96 ?
    C10 H6 . 0.96 ?
    C10 H7 . 0.96 ?
    C11 N2 . 1.355(10) ?
    N2 C12 . 1.459(10) ?
    C12 H8 . 0.96 ?
    C12 H9 . 0.96 ?
    C12 H10 . 0.96 ?
    C14 H11 . 0.96 ?
    C14 H12 . 0.96 ?
    C14 H13 . 0.96 ?
    C15 H14 . 0.96 ?
    C15 H15 . 0.96 ?
    C15 H16 . 0.96 ?
    C16 H17 . 0.96 ?
    C16 H18 . 0.96 ?
    C16 H19 . 0.96 ?
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
    C2 N1 C9 . . 108.1(7) ?
    C2 N1 C10 . . 128.3(8) ?
    C9 N1 C10 . . 123.7(8) ?
    N2 C13 C16 . . 111.2(7) ?
    N2 C13 C15 . . 110.1(7) ?
    C16 C13 C15 . . 111.4(8) ?
    N2 C13 C14 . . 107.8(7) ?
    C16 C13 C14 . . 109.8(7) ?
    C15 C13 C14 . . 106.3(7) ?
    N1 C2 C3 . . 111.4(7) ?
    N1 C2 Br1 . . 119.2(6) ?
    C3 C2 Br1 . . 129.4(6) ?
    C2 C3 C4 . . 105.7(7) ?
    C2 C3 C11 . . 128.1(8) ?
    C4 C3 C11 . . 125.6(7) ?
    C5 C4 C9 . . 118.3(8) ?
    C5 C4 C3 . . 135.1(8) ?
    C9 C4 C3 . . 106.6(7) ?
    C6 C5 C4 . . 119.2(9) ?
    C6 C5 H1 . . 120.4 ?
    C4 C5 H1 . . 120.4 ?
    C5 C6 C7 . . 121.0(9) ?
    C5 C6 H2 . . 119.5 ?
    C7 C6 H2 . . 119.5 ?
    C8 C7 C6 . . 121.4(10) ?
    C8 C7 H4 . . 119.3 ?
    C6 C7 H4 . . 119.3 ?
    C7 C8 C9 . . 118.6(10) ?
    C7 C8 H3 . . 120.7 ?
    C9 C8 H3 . . 120.7 ?
    N1 C9 C8 . . 130.3(9) ?
    N1 C9 C4 . . 108.2(8) ?
    C8 C9 C4 . . 121.5(9) ?
    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 . . 123.0(8) ?
    O1 C11 C3 . . 118.9(8) ?
    N2 C11 C3 . . 118.2(8) ?
    C11 N2 C12 . . 119.7(7) ?
    C11 N2 C13 . . 121.1(7) ?
    C12 N2 C13 . . 117.1(6) ?
    N2 C12 H8 . . 109.5 ?
    N2 C12 H9 . . 109.5 ?
    H8 C12 H9 . . 109.5 ?
    N2 C12 H10 . . 109.5 ?
    H8 C12 H10 . . 109.5 ?
    H9 C12 H10 . . 109.5 ?
    C13 C14 H11 . . 109.5 ?
    C13 C14 H12 . . 109.5 ?
    H11 C14 H12 . . 109.5 ?
    C13 C14 H13 . . 109.5 ?
    H11 C14 H13 . . 109.5 ?
    H12 C14 H13 . . 109.5 ?
    C13 C15 H14 . . 109.5 ?
    C13 C15 H15 . . 109.5 ?
    H14 C15 H15 . . 109.5 ?
    C13 C15 H16 . . 109.5 ?
    H14 C15 H16 . . 109.5 ?
    H15 C15 H16 . . 109.5 ?
    C13 C16 H17 . . 109.5 ?
    C13 C16 H18 . . 109.5 ?
    H17 C16 H18 . . 109.5 ?
    C13 C16 H19 . . 109.5 ?
    H17 C16 H19 . . 109.5 ?
    H18 C16 H19 . . 109.5 ?
