# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a
_database_code_depnum_ccdc_archive 'CCDC 949401'
_audit_update_record             
;
2013-07-09 deposited with the CCDC.
2015-06-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
6-bromo-4a-isopropyl-2-methyl-2,3,4,4a-tetrahydro-1H-carbazole
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H20 Br N'
_chemical_formula_sum            'C16 H20 Br N'
_chemical_formula_weight         306.24

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/m  '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.5180(12)
_cell_length_b                   6.7119(9)
_cell_length_c                   11.6243(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.850(3)
_cell_angle_gamma                90.00
_cell_volume                     742.52(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1904
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      27.97

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorles
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             316
_exptl_absorpt_coefficient_mu    2.752
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3343
_exptl_absorpt_correction_T_max  0.6520
_exptl_absorpt_process_details   'SADABS(Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
Bruker SMART APEX CCD area-detector diffractometer
;
_diffrn_measurement_method       'ω scan'

_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4189
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_av_sigmaI/netI    0.0554
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.75
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2505
_reflns_number_gt                2089
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  
;
SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2009)
;

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+0.0238P] where P=(Fo²+2Fc²)/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     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.021(10)
_refine_ls_number_reflns         2505
_refine_ls_number_parameters     166
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_ref         0.0726
_refine_ls_wR_factor_gt          0.0693
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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
Br1 Br 0.54693(3) 0.90796(7) 0.11712(3) 0.09407(18) Uani 1 1 d . . .
N1 N 0.9869(3) 1.4710(3) 0.3090(2) 0.0625(7) Uani 1 1 d . . .
C1 C 0.8763(3) 1.3563(4) 0.2601(2) 0.0543(8) Uani 1 1 d . . .
C2 C 0.7413(3) 1.4212(6) 0.2318(3) 0.0698(8) Uani 1 1 d . . .
H2A H 0.7164 1.5540 0.2417 0.084 Uiso 1 1 calc R . .
C3 C 0.6455(3) 1.2865(6) 0.1888(3) 0.0697(9) Uani 1 1 d . . .
H3A H 0.5549 1.3275 0.1694 0.084 Uiso 1 1 calc R . .
C4 C 0.6839(3) 1.0914(5) 0.1747(3) 0.0624(8) Uani 1 1 d . . .
C5 C 0.8187(3) 1.0217(5) 0.2024(2) 0.0547(7) Uani 1 1 d . . .
H5A H 0.8425 0.8883 0.1929 0.066 Uiso 1 1 calc R . .
C6 C 0.9145(2) 1.1575(4) 0.2440(2) 0.0464(6) Uani 1 1 d . . .
C7 C 1.0670(2) 1.1404(4) 0.2796(2) 0.0438(6) Uani 1 1 d . . .
C8 C 1.1664(3) 1.0857(5) 0.1786(3) 0.0570(7) Uani 1 1 d . . .
H8A H 1.2629 1.1084 0.2060 0.068 Uiso 1 1 calc R . .
C9 C 1.1560(3) 0.8675(7) 0.1433(3) 0.0787(12) Uani 1 1 d . . .
H9A H 1.2187 0.8424 0.0810 0.118 Uiso 1 1 calc R . .
H9B H 1.0614 0.8381 0.1191 0.118 Uiso 1 1 calc R . .
H9C H 1.1814 0.7845 0.2076 0.118 Uiso 1 1 calc R . .
C10 C 1.1424(5) 1.2206(9) 0.0762(3) 0.1124(17) Uani 1 1 d . . .
H10A H 1.2086 1.1886 0.0175 0.169 Uiso 1 1 calc R . .
H10B H 1.1549 1.3568 0.0994 0.169 Uiso 1 1 calc R . .
H10C H 1.0486 1.2022 0.0467 0.169 Uiso 1 1 calc R . .
C11 C 1.0923(3) 1.3527(4) 0.3197(2) 0.0519(7) Uani 1 1 d . . .
C12 C 1.2269(3) 1.4025(7) 0.3788(3) 0.0612(7) Uani 1 1 d . . .
H12A H 1.2230 1.5379 0.4077 0.073 Uiso 1 1 calc R . .
H12B H 1.3029 1.3947 0.3243 0.073 Uiso 1 1 calc R . .
C13 C 1.2559(3) 1.2592(4) 0.4787(3) 0.0567(7) Uani 1 1 d . . .
H13A H 1.1865 1.2866 0.5381 0.068 Uiso 1 1 calc R . .
C14 C 1.2367(3) 1.0432(4) 0.4411(3) 0.0520(7) Uani 1 1 d . . .
H14A H 1.2481 0.9568 0.5074 0.062 Uiso 1 1 calc R . .
H14B H 1.3089 1.0092 0.3864 0.062 Uiso 1 1 calc R . .
C15 C 1.0917(3) 1.0072(4) 0.3856(2) 0.0466(6) Uani 1 1 d . . .
H15A H 1.0196 1.0339 0.4417 0.056 Uiso 1 1 calc R . .
H15B H 1.0839 0.8685 0.3630 0.056 Uiso 1 1 calc R . .
C16 C 1.4015(3) 1.2974(6) 0.5318(3) 0.0782(10) Uani 1 1 d . . .
H16A H 1.4165 1.2094 0.5959 0.117 Uiso 1 1 calc R . .
H16B H 1.4075 1.4330 0.5576 0.117 Uiso 1 1 calc R . .
H16C H 1.4720 1.2736 0.4752 0.117 Uiso 1 1 calc R . .


_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
Br1 C4 1.907(3) . ?
N1 C11 1.284(3) . ?
N1 C1 1.416(4) . ?
C1 C2 1.391(4) . ?
C1 C6 1.397(4) . ?
C2 C3 1.373(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.370(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.398(4) . ?
C5 C6 1.372(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.508(3) . ?
C7 C11 1.518(4) . ?
C7 C15 1.538(4) . ?
C7 C8 1.562(4) . ?
C8 C10 1.509(5) . ?
C8 C9 1.524(6) . ?
C8 H8A 0.9800 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.483(4) . ?
C12 C13 1.530(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.524(4) . ?
C13 C16 1.530(4) . ?
C13 H13A 0.9800 . ?
C14 C15 1.534(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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
C11 N1 C1 106.2(2) . . ?
C2 C1 C6 120.6(3) . . ?
C2 C1 N1 127.1(3) . . ?
C6 C1 N1 112.3(2) . . ?
C3 C2 C1 119.0(3) . . ?
C3 C2 H2A 120.5 . . ?
C1 C2 H2A 120.5 . . ?
C4 C3 C2 119.7(3) . . ?
C4 C3 H3A 120.1 . . ?
C2 C3 H3A 120.1 . . ?
C3 C4 C5 122.5(3) . . ?
C3 C4 Br1 118.5(2) . . ?
C5 C4 Br1 119.0(3) . . ?
C6 C5 C4 117.5(3) . . ?
C6 C5 H5A 121.3 . . ?
C4 C5 H5A 121.3 . . ?
C5 C6 C1 120.6(2) . . ?
C5 C6 C7 132.7(2) . . ?
C1 C6 C7 106.7(2) . . ?
C6 C7 C11 99.2(2) . . ?
C6 C7 C15 113.5(2) . . ?
C11 C7 C15 106.1(2) . . ?
C6 C7 C8 113.7(2) . . ?
C11 C7 C8 110.9(2) . . ?
C15 C7 C8 112.3(2) . . ?
C10 C8 C9 110.8(3) . . ?
C10 C8 C7 111.4(3) . . ?
C9 C8 C7 113.0(3) . . ?
C10 C8 H8A 107.1 . . ?
C9 C8 H8A 107.1 . . ?
C7 C8 H8A 107.1 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C12 125.1(3) . . ?
N1 C11 C7 115.5(2) . . ?
C12 C11 C7 119.1(3) . . ?
C11 C12 C13 110.8(3) . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C14 C13 C12 111.1(3) . . ?
C14 C13 C16 112.3(3) . . ?
C12 C13 C16 110.7(3) . . ?
C14 C13 H13A 107.5 . . ?
C12 C13 H13A 107.5 . . ?
C16 C13 H13A 107.5 . . ?
C13 C14 C15 112.0(2) . . ?
C13 C14 H14A 109.2 . . ?
C15 C14 H14A 109.2 . . ?
C13 C14 H14B 109.2 . . ?
C15 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C14 C15 C7 111.7(2) . . ?
C14 C15 H15A 109.3 . . ?
C7 C15 H15A 109.3 . . ?
C14 C15 H15B 109.3 . . ?
C7 C15 H15B 109.3 . . ?
H15A C15 H15B 107.9 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 N1 C1 C2 -179.4(3) . . . . ?
C11 N1 C1 C6 2.1(3) . . . . ?
C6 C1 C2 C3 0.8(4) . . . . ?
N1 C1 C2 C3 -177.6(3) . . . . ?
C1 C2 C3 C4 0.0(5) . . . . ?
C2 C3 C4 C5 0.0(5) . . . . ?
C2 C3 C4 Br1 179.0(2) . . . . ?
C3 C4 C5 C6 -0.7(5) . . . . ?
Br1 C4 C5 C6 -179.8(2) . . . . ?
C4 C5 C6 C1 1.5(4) . . . . ?
C4 C5 C6 C7 -178.3(3) . . . . ?
C2 C1 C6 C5 -1.5(4) . . . . ?
N1 C1 C6 C5 177.0(2) . . . . ?
C2 C1 C6 C7 178.3(3) . . . . ?
N1 C1 C6 C7 -3.2(3) . . . . ?
C5 C6 C7 C11 -177.5(3) . . . . ?
C1 C6 C7 C11 2.7(3) . . . . ?
C5 C6 C7 C15 -65.3(4) . . . . ?
C1 C6 C7 C15 114.9(3) . . . . ?
C5 C6 C7 C8 64.7(4) . . . . ?
C1 C6 C7 C8 -115.1(3) . . . . ?
C6 C7 C8 C10 50.5(4) . . . . ?
C11 C7 C8 C10 -60.4(4) . . . . ?
C15 C7 C8 C10 -178.9(3) . . . . ?
C6 C7 C8 C9 -75.1(3) . . . . ?
C11 C7 C8 C9 174.0(3) . . . . ?
C15 C7 C8 C9 55.5(4) . . . . ?
C1 N1 C11 C12 -173.1(2) . . . . ?
C1 N1 C11 C7 -0.1(3) . . . . ?
C6 C7 C11 N1 -1.7(3) . . . . ?
C15 C7 C11 N1 -119.5(3) . . . . ?
C8 C7 C11 N1 118.3(3) . . . . ?
C6 C7 C11 C12 171.7(2) . . . . ?
C15 C7 C11 C12 53.9(3) . . . . ?
C8 C7 C11 C12 -68.4(3) . . . . ?
N1 C11 C12 C13 120.7(3) . . . . ?
C7 C11 C12 C13 -52.0(4) . . . . ?
C11 C12 C13 C14 48.8(3) . . . . ?
C11 C12 C13 C16 174.3(3) . . . . ?
C12 C13 C14 C15 -54.2(3) . . . . ?
C16 C13 C14 C15 -178.8(3) . . . . ?
C13 C14 C15 C7 58.9(3) . . . . ?
C6 C7 C15 C14 -162.5(2) . . . . ?
C11 C7 C15 C14 -54.5(3) . . . . ?
C8 C7 C15 C14 66.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.036
