# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_exp_861
_database_code_depnum_ccdc_archive 'CCDC 1464636'
_audit_update_record             
;
2016-03-11 deposited with the CCDC.
2016-07-12 downloaded from the CCDC.
;
_audit_creation_date             2015-09-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
7,8-dimethyl-11H-benzo[4,5]imidazo[1,2-a]indol-11-one
_chemical_formula_moiety         'C16 H12 N2 O'
_chemical_formula_sum            'C16 H12 N2 O'
_chemical_formula_weight         248.28
_chemical_melting_point          ?
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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.0964(5)
_cell_length_b                   11.9998(8)
_cell_length_c                   14.4434(11)
_cell_angle_alpha                90
_cell_angle_beta                 98.551(6)
_cell_angle_gamma                90
_cell_volume                     1216.27(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1977
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.0450
_cell_measurement_theta_min      3.3500
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.991
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63254
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.881
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8165
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.881
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.954
_diffrn_reflns_theta_min         3.320
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean 16.1213
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.881
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -39.00   48.00   1.0000    1.3700
omega____ theta____ kappa____ phi______ frames
    -       18.1991  -77.0000 -180.0000 87

#__ type_ start__ end____ width___ exp.time_
  2 omega    4.00   83.00   1.0000    1.3700
omega____ theta____ kappa____ phi______ frames
    -       18.1991   57.0000  -60.0000 79

#__ type_ start__ end____ width___ exp.time_
  3 omega   60.00   86.00   1.0000    1.3700
omega____ theta____ kappa____ phi______ frames
    -       18.1991   57.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  -10.00   16.00   1.0000    1.3700
omega____ theta____ kappa____ phi______ frames
    -      -18.9804  -99.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega  -12.00   58.00   1.0000    1.3700
omega____ theta____ kappa____ phi______ frames
    -       18.1991   77.0000  150.0000 70

#__ type_ start__ end____ width___ exp.time_
  6 omega   35.00   94.00   1.0000    1.3700
omega____ theta____ kappa____ phi______ frames
    -       18.1991  178.0000   60.0000 59
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0012130000
_diffrn_orient_matrix_UB_12      0.0192843000
_diffrn_orient_matrix_UB_13      0.0464356000
_diffrn_orient_matrix_UB_21      -0.0032729000
_diffrn_orient_matrix_UB_22      0.0559109000
_diffrn_orient_matrix_UB_23      -0.0162216000
_diffrn_orient_matrix_UB_31      -0.1010653000
_diffrn_orient_matrix_UB_32      -0.0015803000
_diffrn_orient_matrix_UB_33      -0.0062333000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2031
_reflns_number_total             2835
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.091(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2835
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0528
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0524P)²+0.1669P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1149
_refine_ls_wR_factor_ref         0.1286
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.1299(2) 0.39598(14) 0.30963(11) 0.0515(4) Uani 1 1 d . . . . .
C2 C 0.1821(2) 0.48816(14) 0.37754(10) 0.0463(4) Uani 1 1 d . . . . .
C3 C 0.2551(2) 0.62302(13) 0.47005(11) 0.0455(4) Uani 1 1 d . . . . .
C4 C 0.2959(2) 0.72687(14) 0.51102(13) 0.0539(4) Uani 1 1 d . . . . .
H4 H 0.2906 0.7905 0.4740 0.065 Uiso 1 1 calc R . . . .
C5 C 0.3442(2) 0.73485(14) 0.60656(12) 0.0527(4) Uani 1 1 d . . . . .
C6 C 0.3516(2) 0.63779(14) 0.66293(11) 0.0515(4) Uani 1 1 d . . . . .
C7 C 0.3136(2) 0.53388(13) 0.62295(10) 0.0459(4) Uani 1 1 d . . . . .
H7 H 0.3201 0.4700 0.6597 0.055 Uiso 1 1 calc R . . . .
C8 C 0.26588(19) 0.52784(12) 0.52689(10) 0.0398(4) Uani 1 1 d . . . . .
C9 C 0.19311(18) 0.32495(12) 0.46188(9) 0.0391(4) Uani 1 1 d . . . . .
C10 C 0.2116(2) 0.24861(14) 0.53267(11) 0.0490(4) Uani 1 1 d . . . . .
H10 H 0.2453 0.2698 0.5949 0.059 Uiso 1 1 calc R . . . .
C11 C 0.1781(2) 0.13805(14) 0.50777(12) 0.0583(5) Uani 1 1 d . . . . .
H11 H 0.1916 0.0839 0.5544 0.070 Uiso 1 1 calc R . . . .
C12 C 0.1254(3) 0.10592(14) 0.41608(13) 0.0596(5) Uani 1 1 d . . . . .
H12 H 0.1036 0.0310 0.4017 0.072 Uiso 1 1 calc R . . . .
C13 C 0.1048(2) 0.18463(15) 0.34519(12) 0.0551(5) Uani 1 1 d . . . . .
H13 H 0.0681 0.1636 0.2832 0.066 Uiso 1 1 calc R . . . .
C14 C 0.1397(2) 0.29447(13) 0.36855(10) 0.0446(4) Uani 1 1 d . . . . .
C15 C 0.3878(3) 0.84741(15) 0.65069(15) 0.0733(6) Uani 1 1 d . . . . .
H15A H 0.3794 0.9032 0.6027 0.110 Uiso 1 1 calc GR . . . .
H15B H 0.5142 0.8470 0.6854 0.110 Uiso 1 1 calc GR . . . .
H15C H 0.2976 0.8638 0.6922 0.110 Uiso 1 1 calc GR . . . .
C16 C 0.3985(3) 0.64712(18) 0.76744(13) 0.0751(6) Uani 1 1 d . . . . .
H16A H 0.3950 0.5745 0.7950 0.113 Uiso 1 1 calc GR . . . .
H16B H 0.3069 0.6945 0.7905 0.113 Uiso 1 1 calc GR . . . .
H16C H 0.5236 0.6783 0.7837 0.113 Uiso 1 1 calc GR . . . .
N1 N 0.2008(2) 0.59589(12) 0.37604(9) 0.0540(4) Uani 1 1 d . . . . .
N2 N 0.21810(16) 0.44164(10) 0.46515(8) 0.0411(3) Uani 1 1 d . . . . .
O1 O 0.0901(2) 0.40372(12) 0.22544(8) 0.0777(4) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0561(9) 0.0644(11) 0.0346(9) 0.0021(7) 0.0091(6) 0.0046(8)
C2 0.0508(9) 0.0535(10) 0.0352(8) 0.0090(7) 0.0083(6) 0.0069(8)
C3 0.0447(8) 0.0475(9) 0.0460(9) 0.0061(7) 0.0128(6) 0.0052(7)
C4 0.0530(10) 0.0432(10) 0.0694(12) 0.0050(8) 0.0220(8) 0.0043(8)
C5 0.0396(8) 0.0516(10) 0.0683(11) -0.0101(8) 0.0125(7) 0.0007(7)
C6 0.0408(8) 0.0582(11) 0.0539(10) -0.0109(8) 0.0019(7) 0.0042(8)
C7 0.0453(8) 0.0505(10) 0.0402(8) 0.0019(7) 0.0006(6) 0.0053(7)
C8 0.0355(7) 0.0419(9) 0.0421(8) 0.0000(6) 0.0061(6) 0.0026(6)
C9 0.0353(7) 0.0443(9) 0.0374(8) 0.0013(6) 0.0043(5) 0.0033(6)
C10 0.0540(9) 0.0500(10) 0.0417(8) 0.0036(7) 0.0024(6) 0.0043(8)
C11 0.0679(11) 0.0482(10) 0.0593(11) 0.0080(8) 0.0114(8) 0.0018(9)
C12 0.0643(11) 0.0460(10) 0.0703(12) -0.0077(9) 0.0162(9) -0.0050(8)
C13 0.0533(9) 0.0628(12) 0.0499(10) -0.0132(8) 0.0103(7) -0.0037(8)
C14 0.0415(8) 0.0544(10) 0.0381(8) -0.0013(7) 0.0069(6) 0.0019(7)
C15 0.0634(12) 0.0572(12) 0.1005(16) -0.0217(11) 0.0158(10) -0.0039(10)
C16 0.0831(13) 0.0786(14) 0.0575(12) -0.0216(10) -0.0095(9) 0.0033(11)
N1 0.0664(9) 0.0514(9) 0.0463(8) 0.0098(6) 0.0153(6) 0.0076(7)
N2 0.0445(7) 0.0443(7) 0.0338(7) 0.0038(5) 0.0031(5) 0.0032(6)
O1 0.1124(11) 0.0885(10) 0.0311(7) 0.0042(6) 0.0070(6) 0.0027(8)

_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 C2 1.488(2) . ?
C1 C14 1.482(2) . ?
C1 O1 1.2104(18) . ?
C2 N1 1.300(2) . ?
C2 N2 1.3717(18) . ?
C3 C4 1.391(2) . ?
C3 C8 1.402(2) . ?
C3 N1 1.394(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.375(2) . ?
C5 C6 1.417(2) . ?
C5 C15 1.506(2) . ?
C6 C7 1.384(2) . ?
C6 C16 1.501(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.380(2) . ?
C8 N2 1.3749(18) . ?
C9 C10 1.365(2) . ?
C9 C14 1.3937(19) . ?
C9 N2 1.411(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.386(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.377(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.385(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.374(2) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
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
C14 C1 C2 104.28(12) . . ?
O1 C1 C2 127.10(15) . . ?
O1 C1 C14 128.62(16) . . ?
N1 C2 C1 138.09(14) . . ?
N1 C2 N2 114.49(14) . . ?
N2 C2 C1 107.42(13) . . ?
C4 C3 C8 119.40(15) . . ?
C4 C3 N1 129.31(14) . . ?
N1 C3 C8 111.30(14) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.62(15) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 120.11(15) . . ?
C4 C5 C15 119.48(16) . . ?
C6 C5 C15 120.41(16) . . ?
C5 C6 C16 120.01(16) . . ?
C7 C6 C5 120.83(15) . . ?
C7 C6 C16 119.16(16) . . ?
C6 C7 H7 121.0 . . ?
C8 C7 C6 118.05(14) . . ?
C8 C7 H7 121.0 . . ?
C7 C8 C3 121.98(14) . . ?
N2 C8 C3 104.26(13) . . ?
N2 C8 C7 133.75(14) . . ?
C10 C9 C14 122.05(15) . . ?
C10 C9 N2 130.04(13) . . ?
C14 C9 N2 107.90(12) . . ?
C9 C10 H10 121.5 . . ?
C9 C10 C11 117.03(15) . . ?
C11 C10 H10 121.5 . . ?
C10 C11 H11 119.0 . . ?
C12 C11 C10 121.97(16) . . ?
C12 C11 H11 119.0 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.27(16) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 120.7 . . ?
C14 C13 C12 118.52(15) . . ?
C14 C13 H13 120.7 . . ?
C9 C14 C1 108.82(14) . . ?
C13 C14 C1 131.02(14) . . ?
C13 C14 C9 120.15(14) . . ?
C5 C15 H15A 109.5 . . ?
C5 C15 H15B 109.5 . . ?
C5 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C6 C16 H16A 109.5 . . ?
C6 C16 H16B 109.5 . . ?
C6 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C2 N1 C3 103.31(13) . . ?
C2 N2 C8 106.64(13) . . ?
C2 N2 C9 111.57(12) . . ?
C8 N2 C9 141.79(12) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_colour            'light red'
