# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_140303c_0m
_database_code_depnum_ccdc_archive 'CCDC 1033243'
_audit_update_record             
;
2014-11-10 deposited with the CCDC.
2015-03-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        2-methyl-3-phenyl-1H-benzo[g]indole
_chemical_name_common            3'd
_chemical_melting_point          353-355
_chemical_formula_moiety         'C19 H15 N'
_chemical_formula_sum            'C19 H15 N'
_chemical_formula_weight         257.32

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_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. 
;

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

_cell_length_a                   10.182(3)
_cell_length_b                   19.806(7)
_cell_length_c                   8.310(3)
_cell_angle_alpha                90
_cell_angle_beta                 126.517(5)
_cell_angle_gamma                90
_cell_volume                     1346.7(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2464
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      27.60

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.65
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4446
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.693
_diffrn_reflns_theta_max         27.667
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.757
_diffrn_reflns_point_group_measured_fraction_full 0.775
_reflns_number_total             2383
_reflns_number_gt                2274
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.509
_reflns_Friedel_fraction_max     0.512
_reflns_Friedel_fraction_full    0.549

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0495P)²+0.2874P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 736 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.7(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2383
_refine_ls_number_parameters     186
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0847
_refine_ls_wR_factor_gt          0.0829
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.042
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3679(2) 0.08187(9) 0.6170(3) 0.0175(4) Uani 1 1 d . . . . .
C2 C 0.2435(2) 0.08842(9) 0.4076(3) 0.0179(4) Uani 1 1 d . . . . .
C3 C 0.2150(2) 0.04092(10) 0.2630(3) 0.0207(4) Uani 1 1 d . . . . .
H3 H 0.2804 0.0014 0.3045 0.025 Uiso 1 1 calc R U . . .
C4 C 0.0941(3) 0.05138(11) 0.0635(3) 0.0243(4) Uani 1 1 d . . . . .
H4 H 0.0766 0.0192 -0.0323 0.029 Uiso 1 1 calc R U . . .
C5 C -0.0043(3) 0.10964(11) 0.0001(3) 0.0255(4) Uani 1 1 d . . . . .
H5 H -0.0878 0.1167 -0.1383 0.031 Uiso 1 1 calc R U . . .
C6 C 0.0202(3) 0.15615(11) 0.1379(3) 0.0229(4) Uani 1 1 d . . . . .
H6 H -0.0469 0.1952 0.0932 0.027 Uiso 1 1 calc R U . . .
C7 C 0.1436(2) 0.14709(9) 0.3452(3) 0.0195(4) Uani 1 1 d . . . . .
C8 C 0.1686(2) 0.19441(9) 0.4912(3) 0.0215(4) Uani 1 1 d . . . . .
H8 H 0.1030 0.2340 0.4473 0.026 Uiso 1 1 calc R U . . .
C9 C 0.2837(2) 0.18440(9) 0.6915(3) 0.0210(4) Uani 1 1 d . . . . .
H9 H 0.2950 0.2158 0.7855 0.025 Uiso 1 1 calc R U . . .
C10 C 0.3864(2) 0.12673(10) 0.7585(3) 0.0184(4) Uani 1 1 d . . . . .
C11 C 0.5221(2) 0.10345(9) 0.9527(3) 0.0178(4) Uani 1 1 d . . . . .
C12 C 0.5817(2) 0.04633(9) 0.9214(3) 0.0183(4) Uani 1 1 d . . . . .
C13 C 0.7197(3) 0.00050(10) 1.0639(3) 0.0215(4) Uani 1 1 d . . . . .
H13A H 0.8113 0.0087 1.0574 0.032 Uiso 1 1 calc R U . . .
H13B H 0.6839 -0.0465 1.0278 0.032 Uiso 1 1 calc R U . . .
H13C H 0.7545 0.0092 1.2002 0.032 Uiso 1 1 calc R U . . .
C14 C 0.5816(2) 0.13407(9) 1.1479(3) 0.0177(4) Uani 1 1 d . . . . .
C15 C 0.7479(2) 0.14385(9) 1.2992(3) 0.0195(4) Uani 1 1 d . . . . .
H15 H 0.8260 0.1304 1.2779 0.023 Uiso 1 1 calc R U . . .
C16 C 0.8006(2) 0.17308(10) 1.4807(3) 0.0212(4) Uani 1 1 d . . . . .
H16 H 0.9141 0.1790 1.5829 0.025 Uiso 1 1 calc R U . . .
C17 C 0.6876(3) 0.19365(9) 1.5127(3) 0.0229(4) Uani 1 1 d . . . . .
H17 H 0.7234 0.2146 1.6354 0.028 Uiso 1 1 calc R U . . .
C18 C 0.5224(3) 0.18351(10) 1.3653(3) 0.0228(4) Uani 1 1 d . . . . .
H18 H 0.4451 0.1966 1.3883 0.027 Uiso 1 1 calc R U . . .
C19 C 0.4692(3) 0.15425(9) 1.1835(3) 0.0208(4) Uani 1 1 d . . . . .
H19 H 0.3556 0.1479 1.0827 0.025 Uiso 1 1 calc R U . . .
N1 N 0.4870(2) 0.03357(8) 0.7181(2) 0.0182(3) Uani 1 1 d . . . . .
H1 H 0.493(3) -0.0027(14) 0.664(4) 0.031(7) Uiso 1 1 d . . . . .


_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
C1 N1 1.371(3) . ?
C1 C10 1.394(3) . ?
C1 C2 1.423(3) . ?
C2 C3 1.414(3) . ?
C2 C7 1.423(3) . ?
C3 C4 1.370(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.409(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.371(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.415(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.431(3) . ?
C8 C9 1.365(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.420(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.440(3) . ?
C11 C12 1.379(3) . ?
C11 C14 1.482(3) . ?
C12 N1 1.382(2) . ?
C12 C13 1.490(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.397(3) . ?
C14 C19 1.400(3) . ?
C15 C16 1.391(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.385(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.392(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
N1 H1 0.87(3) . ?

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
N1 C1 C10 107.54(17) . . ?
N1 C1 C2 129.19(17) . . ?
C10 C1 C2 123.27(17) . . ?
C3 C2 C7 119.54(17) . . ?
C3 C2 C1 124.17(17) . . ?
C7 C2 C1 116.29(16) . . ?
C4 C3 C2 120.65(18) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 120.22(19) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 120.2(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 121.30(19) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C6 C7 C2 118.13(17) . . ?
C6 C7 C8 122.01(17) . . ?
C2 C7 C8 119.86(17) . . ?
C9 C8 C7 121.97(17) . . ?
C9 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
C8 C9 C10 119.52(18) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C1 C10 C9 118.91(18) . . ?
C1 C10 C11 107.41(17) . . ?
C9 C10 C11 133.56(18) . . ?
C12 C11 C10 106.72(17) . . ?
C12 C11 C14 127.08(18) . . ?
C10 C11 C14 126.17(17) . . ?
C11 C12 N1 108.40(17) . . ?
C11 C12 C13 131.45(18) . . ?
N1 C12 C13 120.14(17) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 118.36(18) . . ?
C15 C14 C11 121.93(18) . . ?
C19 C14 C11 119.70(18) . . ?
C16 C15 C14 120.83(18) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C17 C16 C15 120.10(19) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C18 C17 C16 119.82(19) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C19 120.22(19) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C14 120.64(19) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?
C1 N1 C12 109.92(16) . . ?
C1 N1 H1 124.6(18) . . ?
C12 N1 H1 125.0(18) . . ?

_refine_diff_density_max         0.198
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.036

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: C2H5OH'
_chemical_compound_source        1-naphthylamine
_chemical_properties_physical    Heat-sensitive
