##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the data    # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_journal_date_recd_electronic     2016-09-01
_journal_date_accepted     2016-09-16
_journal_name_full     'IUCrData'
_journal_year     2016
_journal_volume     1
_journal_issue      9
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2414314616014681
_journal_coeditor_code     BV4003
_publ_contact_author_name
;
Professor Jerry P. Jasinski
;
_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     ?
_publ_contact_author_phone     ?
_publ_section_title
;
tert-Butyl
2,3-dihydro-1H-cyclopenta[b]indole-4-carboxylate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Jordon, Jason A.' .
;
Department of Biological and Chemical Sciences,
University of the West Indies, Cave Hill
Barbados
;
    'Badenock, Jeanese C.' .
;
Department of Biological and Chemical Sciences,
University of the West Indies, Cave Hill
Barbados
;
    'Gribble, Gordon W.' .
;
Department of Chemistry,
Dartmouth College
Hanover, NH 03755-3564
USA
;
    'Kaur, Manpreet' .
;
Department of Chemistry,
Keene State College,
229 Main Street, Keene,
NH 03435-2001, USA
;
    'Jasinski, Jerry P.' .
;
Department of Chemistry,
Keene State College,
229 Main Street, Keene,
NH 03435-2001, USA
;
_publ_section_synopsis
;
The title molecule is essentially planar and contains one of the three methyl
groups from the tert-butyl group within the plane. A mirror plane
through the plane of the molecule allows the third methyl group outside the
plane to be symmetrically generated opposite the second one.
;
_chemical_name_systematic
;
tert-Butyl
2,3-dihydro-1H-cyclopenta[b]indole-4-carboxylate
;
_chemical_name_common
;
2,3-dihydro-1H-cyclopenta[b]indole-4-carboxylic acid
tert-butyl ester
;
_chemical_formula_moiety     'C16 H19 N O2'
_chemical_formula_sum     'C16 H19 N O2'
_chemical_formula_iupac     'C16 H19 N O2'
_chemical_formula_weight     257.32
_chemical_melting_point     ?
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system     orthorhombic
_space_group_name_H-M_alt     'P n m a'
_space_group_name_Hall     '-P 2ac 2n'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z'
    'x+1/2, -y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, y, -z-1/2'
    'x, -y-1/2, z'
    '-x-1/2, y-1/2, z-1/2'
_cell_length_a     19.6761(11)
_cell_length_b     7.2330(4)
_cell_length_c     9.9258(7)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     1412.61(15)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4596
_cell_measurement_theta_min     3.48
_cell_measurement_theta_max     32.26
_cell_measurement_temperature     173(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.38
_exptl_crystal_size_mid     0.26
_exptl_crystal_size_min     0.15
_exptl_crystal_density_diffrn     1.210
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     552
_exptl_absorpt_coefficient_mu     0.079
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO & CrysAlis RED; Rigaku-Oxford Diffraction, 2012)
;
_shelx_estimated_absorpt_T_min     0.970
_shelx_estimated_absorpt_T_max     0.988
_exptl_absorpt_correction_T_min     0.9704
_exptl_absorpt_correction_T_max     0.9882
_exptl_special_details     ?
_diffrn_ambient_temperature     173(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Rigaku-Oxford Diffraction'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     16.1500
_diffrn_reflns_number     12388
_diffrn_reflns_av_R_equivalents     0.0291
_diffrn_reflns_theta_min     3.485
_diffrn_reflns_theta_max     27.875
_diffrn_reflns_theta_full     25.000
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -25
_diffrn_reflns_limit_h_max     24
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     13
_refine_special_details     ?
_reflns_number_total     1808
_reflns_number_gt     1486
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0672
_refine_ls_R_factor_gt     0.0560
_refine_ls_wR_factor_gt     0.1389
_refine_ls_wR_factor_ref     0.1465
_refine_ls_goodness_of_fit_ref     1.105
_refine_ls_restrained_S_all     1.105
_refine_ls_number_reflns     1808
_refine_ls_number_parameters     113
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0562P)²+0.3940P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.162
_refine_diff_density_min     -0.178
_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'
    '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'
_computing_data_collection
;
CrysAlis PRO (Rigaku-Oxford Diffraction, 2012)
;
_computing_cell_refinement
;
CrysAlis PRO (Rigaku-Oxford Diffraction, 2012)
;
_computing_data_reduction
;
CrysAlis RED (Rigaku-Oxford Diffraction, 2012)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015b)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015a)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.32442(9) 0.2500 1.10343(19) 0.0736(6) Uani d 1 . .
    O O2 0.35771(8) 0.2500 0.88593(17) 0.0631(5) Uani d 1 . .
    N N1 0.43643(8) 0.2500 1.04482(17) 0.0438(4) Uani d 1 . .
    C C1 0.49003(10) 0.2500 0.9521(2) 0.0408(4) Uani d 1 . .
    C C2 0.49512(11) 0.2500 0.8034(2) 0.0484(5) Uani d 1 . .
    H H2A 0.4739 0.3616 0.7640 0.058 Uiso calc 0.5 . .
    H H2B 0.4739 0.1384 0.7640 0.058 Uiso calc 0.5 . .
    C C3 0.57309(12) 0.2500 0.7828(2) 0.0586(6) Uani d 1 . .
    H H3A 0.5869 0.1391 0.7311 0.070 Uiso calc 0.5 . .
    H H3B 0.5869 0.3609 0.7311 0.070 Uiso calc 0.5 . .
    C C4 0.60802(11) 0.2500 0.9211(2) 0.0547(6) Uani d 1 . .
    H H4A 0.6366 0.1385 0.9331 0.066 Uiso calc 0.5 . .
    H H4B 0.6366 0.3615 0.9331 0.066 Uiso calc 0.5 . .
    C C5 0.54989(10) 0.2500 1.0164(2) 0.0442(5) Uani d 1 . .
    C C6 0.53714(12) 0.2500 1.1579(2) 0.0490(5) Uani d 1 . .
    C C7 0.57817(15) 0.2500 1.2717(3) 0.0674(7) Uani d 1 . .
    H H7 0.6263 0.2500 1.2632 0.081 Uiso calc 1 . .
    C C8 0.5485(2) 0.2500 1.3961(3) 0.0874(10) Uani d 1 . .
    H H8 0.5765 0.2500 1.4741 0.105 Uiso calc 1 . .
    C C9 0.4784(2) 0.2500 1.4109(3) 0.0863(10) Uani d 1 . .
    H H9 0.4594 0.2500 1.4989 0.104 Uiso calc 1 . .
    C C10 0.43543(15) 0.2500 1.3003(2) 0.0652(7) Uani d 1 . .
    H H10 0.3874 0.2500 1.3104 0.078 Uiso calc 1 . .
    C C11 0.46572(12) 0.2500 1.1746(2) 0.0471(5) Uani d 1 . .
    C C12 0.36713(10) 0.2500 1.0180(2) 0.0513(5) Uani d 1 . .
    C C13 0.28904(12) 0.2500 0.8262(3) 0.0673(7) Uani d 1 . .
    C C14 0.30593(17) 0.2500 0.6773(3) 0.0996(12) Uani d 1 . .
    H H14A 0.2638 0.2500 0.6248 0.149 Uiso calc 1 . .
    H H14B 0.3325 0.3606 0.6554 0.149 Uiso calc 0.5 . .
    H H14C 0.3325 0.1394 0.6554 0.149 Uiso calc 0.5 . .
    C C15 0.25196(10) 0.0761(3) 0.8664(2) 0.0919(8) Uani d 1 . .
    H H15A 0.2814 -0.0311 0.8514 0.138 Uiso calc 1 . .
    H H15B 0.2106 0.0635 0.8121 0.138 Uiso calc 1 . .
    H H15C 0.2397 0.0830 0.9620 0.138 Uiso calc 1 . .
_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
    O1 C12 . 1.194(3) ?
    O2 C12 . 1.324(3) ?
    O2 C13 . 1.476(3) ?
    N1 C1 . 1.400(3) ?
    N1 C11 . 1.411(3) ?
    N1 C12 . 1.389(3) ?
    C1 C2 . 1.479(3) ?
    C1 C5 . 1.340(3) ?
    C2 H2A . 0.9900 ?
    C2 H2B . 0.9900 ?
    C2 C3 . 1.548(3) ?
    C3 H3A . 0.9900 ?
    C3 H3B . 0.9900 ?
    C3 C4 . 1.536(3) ?
    C4 H4A . 0.9900 ?
    C4 H4B . 0.9900 ?
    C4 C5 . 1.484(3) ?
    C5 C6 . 1.427(3) ?
    C6 C7 . 1.388(3) ?
    C6 C11 . 1.415(3) ?
    C7 H7 . 0.9500 ?
    C7 C8 . 1.365(4) ?
    C8 H8 . 0.9500 ?
    C8 C9 . 1.388(5) ?
    C9 H9 . 0.9500 ?
    C9 C10 . 1.385(4) ?
    C10 H10 . 0.9500 ?
    C10 C11 . 1.383(3) ?
    C13 C14 . 1.515(4) ?
    C13 C15 7_565 1.508(3) ?
    C13 C15 . 1.508(3) ?
    C14 H14A . 0.9800 ?
    C14 H14B . 0.9800 ?
    C14 H14C . 0.9800 ?
    C15 H15A . 0.9800 ?
    C15 H15B . 0.9800 ?
    C15 H15C . 0.9800 ?
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
    C12 O2 C13 . . 121.74(19) ?
    C1 N1 C11 . . 107.02(16) ?
    C12 N1 C1 . . 127.82(18) ?
    C12 N1 C11 . . 125.16(18) ?
    N1 C1 C2 . . 135.00(17) ?
    C5 C1 N1 . . 110.42(18) ?
    C5 C1 C2 . . 114.58(19) ?
    C1 C2 H2A . . 111.5 ?
    C1 C2 H2B . . 111.5 ?
    C1 C2 C3 . . 101.51(17) ?
    H2A C2 H2B . . 109.3 ?
    C3 C2 H2A . . 111.5 ?
    C3 C2 H2B . . 111.5 ?
    C2 C3 H3A . . 109.9 ?
    C2 C3 H3B . . 109.9 ?
    H3A C3 H3B . . 108.3 ?
    C4 C3 C2 . . 108.96(19) ?
    C4 C3 H3A . . 109.9 ?
    C4 C3 H3B . . 109.9 ?
    C3 C4 H4A . . 111.2 ?
    C3 C4 H4B . . 111.2 ?
    H4A C4 H4B . . 109.1 ?
    C5 C4 C3 . . 103.01(17) ?
    C5 C4 H4A . . 111.2 ?
    C5 C4 H4B . . 111.2 ?
    C1 C5 C4 . . 111.95(19) ?
    C1 C5 C6 . . 108.33(19) ?
    C6 C5 C4 . . 139.71(19) ?
    C7 C6 C5 . . 134.3(2) ?
    C7 C6 C11 . . 118.8(2) ?
    C11 C6 C5 . . 106.85(18) ?
    C6 C7 H7 . . 120.4 ?
    C8 C7 C6 . . 119.1(3) ?
    C8 C7 H7 . . 120.4 ?
    C7 C8 H8 . . 119.3 ?
    C7 C8 C9 . . 121.4(3) ?
    C9 C8 H8 . . 119.3 ?
    C8 C9 H9 . . 119.3 ?
    C10 C9 C8 . . 121.5(3) ?
    C10 C9 H9 . . 119.3 ?
    C9 C10 H10 . . 121.5 ?
    C11 C10 C9 . . 116.9(3) ?
    C11 C10 H10 . . 121.5 ?
    N1 C11 C6 . . 107.37(18) ?
    C10 C11 N1 . . 130.4(2) ?
    C10 C11 C6 . . 122.2(2) ?
    O1 C12 O2 . . 127.2(2) ?
    O1 C12 N1 . . 123.7(2) ?
    O2 C12 N1 . . 109.11(19) ?
    O2 C13 C14 . . 101.0(2) ?
    O2 C13 C15 . . 109.67(14) ?
    O2 C13 C15 . 7_565 109.67(14) ?
    C15 C13 C14 7_565 . 111.38(16) ?
    C15 C13 C14 . . 111.38(16) ?
    C15 C13 C15 7_565 . 113.0(2) ?
    C13 C14 H14A . . 109.5 ?
    C13 C14 H14B . . 109.5 ?
    C13 C14 H14C . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 109.5 ?
    C13 C15 H15A . . 109.5 ?
    C13 C15 H15B . . 109.5 ?
    C13 C15 H15C . . 109.5 ?
    H15A C15 H15B . . 109.5 ?
    H15A C15 H15C . . 109.5 ?
    H15B C15 H15C . . 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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    N1 C1 C2 C3 . . . . 180.0000(10)
                                   ?
    N1 C1 C5 C4 . . . . 180.000000 ?
    N1 C1 C5 C6 . . . . 0.0000(10)
                                 ?
    C1 N1 C11 C6 . . . . 0.0000(10)
                                  ?
    C1 N1 C11 C10 . . . . 180.0000(10)
                                     ?
    C1 N1 C12 O1 . . . . 180.0000(10)
                                    ?
    C1 N1 C12 O2 . . . . 0.0000(10)
                                  ?
    C1 C2 C3 C4 . . . . 0.000000 ?
    C1 C5 C6 C7 . . . . 180.0000(10)
                                   ?
    C1 C5 C6 C11 . . . . 0.0000(10)
                                  ?
    C2 C1 C5 C4 . . . . 0.0000(10)
                                 ?
    C2 C1 C5 C6 . . . . 180.000000 ?
    C2 C3 C4 C5 . . . . 0.000000 ?
    C3 C4 C5 C1 . . . . 0.000000 ?
    C3 C4 C5 C6 . . . . 180.0000(10)
                                   ?
    C4 C5 C6 C7 . . . . 0.0000(10)
                                 ?
    C4 C5 C6 C11 . . . . 180.0000(10)
                                    ?
    C5 C1 C2 C3 . . . . 0.000000 ?
    C5 C6 C7 C8 . . . . 180.0000(10)
                                   ?
    C5 C6 C11 N1 . . . . 0.0000(10)
                                  ?
    C5 C6 C11 C10 . . . . 180.0000(10)
                                     ?
    C6 C7 C8 C9 . . . . 0.0000(10)
                                 ?
    C7 C6 C11 N1 . . . . 180.0000(10)
                                    ?
    C7 C6 C11 C10 . . . . 0.0000(10)
                                   ?
    C7 C8 C9 C10 . . . . 0.0000(10)
                                  ?
    C8 C9 C10 C11 . . . . 0.0000(10)
                                   ?
    C9 C10 C11 N1 . . . . 180.0000(10)
                                     ?
    C9 C10 C11 C6 . . . . 0.0000(10)
                                   ?
    C11 N1 C1 C2 . . . . 180.0000(10)
                                    ?
    C11 N1 C1 C5 . . . . 0.000000 ?
    C11 N1 C12 O1 . . . . 0.0000(10)
                                   ?
    C11 N1 C12 O2 . . . . 180.000000 ?
    C11 C6 C7 C8 . . . . 0.0000(10)
                                  ?
    C12 O2 C13 C14 . . . . 180.000000 ?
    C12 O2 C13 C15 . . . 7_565 62.35(18) ?
    C12 O2 C13 C15 . . . . -62.35(18) ?
    C12 N1 C1 C2 . . . . 0.0000(10)
                                  ?
    C12 N1 C1 C5 . . . . 180.000000 ?
    C12 N1 C11 C6 . . . . 180.0000(10)
                                     ?
    C12 N1 C11 C10 . . . . 0.0000(10)
                                    ?
    C13 O2 C12 O1 . . . . 0.0000(10)
                                   ?
    C13 O2 C12 N1 . . . . 180.000000 ?
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
    C10 H10 O1 . 0.95 2.40 2.931(3) 115.1
    C15 H15C O1 . 0.98 2.49 3.025(3) 113.9
_shelxl_version_number     2014/6
