# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# 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. 
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#######################################################################

data_mo_160318LT_0m
_database_code_depnum_ccdc_archive 'CCDC 1480824'
_audit_update_record             
;
2016-05-19 deposited with the CCDC.
2017-04-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        
'methyl 2-(3-methyl-11H-benzo[4,5]imidazo[2,1-a]isoindol-11-yl)acetate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 N2 O2'
_chemical_formula_weight         292.33

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.4244(9)
_cell_length_b                   8.0614(6)
_cell_length_c                   14.7164(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.607(2)
_cell_angle_gamma                90
_cell_volume                     1448.78(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4149
_cell_measurement_theta_min      2.8164
_cell_measurement_theta_max      26.3552

_exptl_crystal_description       Lump
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9082
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(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 8.3333
_diffrn_reflns_number            11617
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.816
_diffrn_reflns_theta_max         26.379
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2954
_reflns_number_gt                2477
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  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)+(0.0451P)²+0.6018P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2954
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.0982
_refine_ls_wR_factor_gt          0.0917
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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
O1 O 0.18653(7) 0.03180(13) 0.25396(7) 0.0280(2) Uani 1 1 d . . . . .
O2 O 0.14514(8) 0.25657(13) 0.33094(6) 0.0279(2) Uani 1 1 d . . . . .
N1 N 0.36507(8) 0.18864(13) 0.50895(7) 0.0177(2) Uani 1 1 d . . . . .
N2 N 0.46072(9) 0.08254(13) 0.64190(7) 0.0187(2) Uani 1 1 d . . . . .
C1 C 0.07153(12) 0.0101(2) 0.21687(12) 0.0404(4) Uani 1 1 d . . . . .
H16 H 0.0321 -0.0121 0.2675 0.061 Uiso 1 1 calc R U . . .
H3 H 0.0619 -0.0837 0.1737 0.061 Uiso 1 1 calc R U . . .
H1 H 0.0425 0.1111 0.1843 0.061 Uiso 1 1 calc R U . . .
C2 C 0.21221(11) 0.16451(16) 0.30886(8) 0.0202(3) Uani 1 1 d . . . . .
C3 C 0.33428(10) 0.18076(16) 0.33565(8) 0.0184(3) Uani 1 1 d . . . . .
H14 H 0.3624 0.2345 0.2842 0.022 Uiso 1 1 calc R U . . .
H15 H 0.3666 0.0683 0.3439 0.022 Uiso 1 1 calc R U . . .
C4 C 0.37307(10) 0.28018(16) 0.42378(8) 0.0188(3) Uani 1 1 d . . . . .
H13 H 0.3322 0.3874 0.4216 0.023 Uiso 1 1 calc R U . . .
C5 C 0.49613(10) 0.31200(15) 0.44013(9) 0.0183(3) Uani 1 1 d . . . . .
C6 C 0.54839(10) 0.24326(15) 0.52354(8) 0.0177(3) Uani 1 1 d . . . . .
C7 C 0.66051(11) 0.25589(16) 0.55315(9) 0.0197(3) Uani 1 1 d . . . . .
H8 H 0.6947 0.2075 0.6100 0.024 Uiso 1 1 calc R U . . .
C8 C 0.72252(11) 0.34074(16) 0.49811(9) 0.0219(3) Uani 1 1 d . . . . .
C9 C 0.84419(11) 0.36212(19) 0.52995(10) 0.0299(3) Uani 1 1 d . . . . .
H9 H 0.8590 0.4724 0.5574 0.045 Uiso 1 1 calc R U . . .
H2 H 0.8813 0.3507 0.4770 0.045 Uiso 1 1 calc R U . . .
H10 H 0.8714 0.2771 0.5761 0.045 Uiso 1 1 calc R U . . .
C10 C 0.46438(10) 0.16532(15) 0.56579(8) 0.0165(3) Uani 1 1 d . . . . .
C11 C 0.34940(10) 0.04857(15) 0.63498(8) 0.0185(3) Uani 1 1 d . . . . .
C12 C 0.28738(11) 0.11789(15) 0.55341(8) 0.0185(3) Uani 1 1 d . . . . .
C13 C 0.17346(11) 0.10828(18) 0.53406(9) 0.0243(3) Uani 1 1 d . . . . .
H7 H 0.1317 0.1576 0.4803 0.029 Uiso 1 1 calc R U . . .
C14 C 0.12420(11) 0.02319(19) 0.59716(10) 0.0272(3) Uani 1 1 d . . . . .
H6 H 0.0466 0.0147 0.5864 0.033 Uiso 1 1 calc R U . . .
C15 C 0.18505(12) -0.05090(18) 0.67645(9) 0.0262(3) Uani 1 1 d . . . . .
H5 H 0.1480 -0.1103 0.7172 0.031 Uiso 1 1 calc R U . . .
C16 C 0.29760(11) -0.03916(16) 0.69630(9) 0.0223(3) Uani 1 1 d . . . . .
H4 H 0.3386 -0.0893 0.7501 0.027 Uiso 1 1 calc R U . . .
C17 C 0.55713(11) 0.39456(16) 0.38424(9) 0.0214(3) Uani 1 1 d . . . . .
H12 H 0.5229 0.4406 0.3267 0.026 Uiso 1 1 calc R U . . .
C18 C 0.66962(11) 0.40829(16) 0.41431(9) 0.0227(3) Uani 1 1 d . . . . .
H11 H 0.7119 0.4655 0.3766 0.027 Uiso 1 1 calc R U . . .


_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
O1 C2 1.3432(16) . ?
O1 C1 1.4432(16) . ?
O2 C2 1.2044(16) . ?
N1 C10 1.3702(16) . ?
N1 C12 1.3848(16) . ?
N1 C4 1.4735(16) . ?
N2 C10 1.3118(16) . ?
N2 C11 1.3952(16) . ?
C1 H16 0.9800 . ?
C1 H3 0.9800 . ?
C1 H1 0.9800 . ?
C2 C3 1.5009(17) . ?
C3 C4 1.5254(17) . ?
C3 H14 0.9900 . ?
C3 H15 0.9900 . ?
C4 C5 1.5252(17) . ?
C4 H13 1.0000 . ?
C5 C17 1.3868(18) . ?
C5 C6 1.3936(18) . ?
C6 C7 1.3847(18) . ?
C6 C10 1.4525(17) . ?
C7 C8 1.3953(19) . ?
C7 H8 0.9500 . ?
C8 C18 1.3967(19) . ?
C8 C9 1.5080(18) . ?
C9 H9 0.9800 . ?
C9 H2 0.9800 . ?
C9 H10 0.9800 . ?
C11 C16 1.3937(18) . ?
C11 C12 1.4165(18) . ?
C12 C13 1.3936(18) . ?
C13 C14 1.384(2) . ?
C13 H7 0.9500 . ?
C14 C15 1.402(2) . ?
C14 H6 0.9500 . ?
C15 C16 1.3782(19) . ?
C15 H5 0.9500 . ?
C16 H4 0.9500 . ?
C17 C18 1.3905(19) . ?
C17 H12 0.9500 . ?
C18 H11 0.9500 . ?

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
C2 O1 C1 115.67(11) . . ?
C10 N1 C12 106.42(10) . . ?
C10 N1 C4 113.19(10) . . ?
C12 N1 C4 140.37(11) . . ?
C10 N2 C11 103.13(10) . . ?
O1 C1 H16 109.5 . . ?
O1 C1 H3 109.5 . . ?
H16 C1 H3 109.5 . . ?
O1 C1 H1 109.5 . . ?
H16 C1 H1 109.5 . . ?
H3 C1 H1 109.5 . . ?
O2 C2 O1 123.61(12) . . ?
O2 C2 C3 126.25(12) . . ?
O1 C2 C3 110.13(10) . . ?
C2 C3 C4 114.52(10) . . ?
C2 C3 H14 108.6 . . ?
C4 C3 H14 108.6 . . ?
C2 C3 H15 108.6 . . ?
C4 C3 H15 108.6 . . ?
H14 C3 H15 107.6 . . ?
N1 C4 C5 99.95(9) . . ?
N1 C4 C3 113.57(10) . . ?
C5 C4 C3 111.90(10) . . ?
N1 C4 H13 110.3 . . ?
C5 C4 H13 110.3 . . ?
C3 C4 H13 110.3 . . ?
C17 C5 C6 119.76(12) . . ?
C17 C5 C4 128.95(12) . . ?
C6 C5 C4 111.29(11) . . ?
C7 C6 C5 121.77(12) . . ?
C7 C6 C10 131.13(12) . . ?
C5 C6 C10 107.10(11) . . ?
C6 C7 C8 118.97(12) . . ?
C6 C7 H8 120.5 . . ?
C8 C7 H8 120.5 . . ?
C7 C8 C18 118.90(12) . . ?
C7 C8 C9 120.31(12) . . ?
C18 C8 C9 120.78(12) . . ?
C8 C9 H9 109.5 . . ?
C8 C9 H2 109.5 . . ?
H9 C9 H2 109.5 . . ?
C8 C9 H10 109.5 . . ?
H9 C9 H10 109.5 . . ?
H2 C9 H10 109.5 . . ?
N2 C10 N1 114.98(11) . . ?
N2 C10 C6 136.56(12) . . ?
N1 C10 C6 108.46(11) . . ?
C16 C11 N2 128.47(12) . . ?
C16 C11 C12 120.32(12) . . ?
N2 C11 C12 111.21(11) . . ?
N1 C12 C13 134.14(12) . . ?
N1 C12 C11 104.19(11) . . ?
C13 C12 C11 121.66(12) . . ?
C14 C13 C12 116.63(13) . . ?
C14 C13 H7 121.7 . . ?
C12 C13 H7 121.7 . . ?
C13 C14 C15 122.16(13) . . ?
C13 C14 H6 118.9 . . ?
C15 C14 H6 118.9 . . ?
C16 C15 C14 121.19(13) . . ?
C16 C15 H5 119.4 . . ?
C14 C15 H5 119.4 . . ?
C15 C16 C11 117.97(12) . . ?
C15 C16 H4 121.0 . . ?
C11 C16 H4 121.0 . . ?
C5 C17 C18 118.45(12) . . ?
C5 C17 H12 120.8 . . ?
C18 C17 H12 120.8 . . ?
C17 C18 C8 122.14(12) . . ?
C17 C18 H11 118.9 . . ?
C8 C18 H11 118.9 . . ?

_refine_diff_density_max         0.241
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.040

_shelxl_version_number           2014/6



