# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_ODMIM
_database_code_depnum_ccdc_archive 'CCDC 1003612'
_audit_update_record             
;
2015-01-16 deposited with the CCDC.
2015-04-20 downloaded from the CCDC.
;
_audit_creation_date             2015-01-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.09 svn.r3130 for OlexSys, GUI svn.r4987)
;
_chemical_name_common            ?
_chemical_name_systematic        N,N-dimethylaniline-N-naphthalimide
_chemical_formula_moiety         'C20 H16 N2 O2'
_chemical_formula_sum            'C20 H16 N2 O2'
_chemical_formula_weight         316.35
_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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'
'-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                   17.3700(9)
_cell_length_b                   29.0684(13)
_cell_length_c                   8.8805(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.498(4)
_cell_angle_gamma                90
_cell_volume                     4470.1(4)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    5796
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      28.5219
_cell_measurement_theta_min      3.2607
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76397
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1992
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.891
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            23905
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.891
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.585
_diffrn_reflns_theta_min         3.267
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.891
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -46.00   26.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9090  -38.0000  -30.0000 72

#__ type_ start__ end____ width___ exp.time_
  2 omega  -15.00   72.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9090   38.0000  -30.0000 87

#__ type_ start__ end____ width___ exp.time_
  3 omega   23.00   49.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9090   38.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  -53.00   26.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9090  -38.0000  120.0000 79

#__ type_ start__ end____ width___ exp.time_
  5 omega    4.00   60.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9090   38.0000  -90.0000 56

#__ type_ start__ end____ width___ exp.time_
  6 omega   49.00   87.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9090   77.0000  150.0000 38

#__ type_ start__ end____ width___ exp.time_
  7 omega   28.00   89.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9090   77.0000   90.0000 61
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0108085000
_diffrn_orient_matrix_UB_12      -0.0139077000
_diffrn_orient_matrix_UB_13      0.0637960000
_diffrn_orient_matrix_UB_21      -0.0255660000
_diffrn_orient_matrix_UB_22      0.0125473000
_diffrn_orient_matrix_UB_23      0.0431219000
_diffrn_orient_matrix_UB_31      -0.0301130000
_diffrn_orient_matrix_UB_32      -0.0156375000
_diffrn_orient_matrix_UB_33      -0.0221558000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3685
_reflns_number_total             5091
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_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 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_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    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         5091
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0429
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0588P)²+1.9421P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1247
_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), C5(H5), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C23(H23), C24(H24), C30(H30), C31(H31), C32(H32)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
N1 N 0.82485(7) 0.78584(4) 0.66712(12) 0.0307(3) Uani 1 1 d . . . . .
N2 N 0.81869(6) 0.59248(3) 0.66643(11) 0.0223(2) Uani 1 1 d . . . . .
N3 N 0.5000 0.45877(6) 0.7500 0.0460(5) Uani 1 2 d S T P . .
N4 N 0.5000 0.65253(5) 0.7500 0.0226(3) Uani 1 2 d S T P . .
O1 O 0.91587(6) 0.59211(3) 0.85388(10) 0.0336(2) Uani 1 1 d . . . . .
O2 O 0.71892(5) 0.59231(3) 0.48454(10) 0.0302(2) Uani 1 1 d . . . . .
O3 O 0.59340(6) 0.65259(3) 0.94404(10) 0.0358(3) Uani 1 1 d . . . . .
C1 C 0.76186(9) 0.81167(5) 0.72215(17) 0.0356(3) Uani 1 1 d . . . . .
H1A H 0.7575 0.8044 0.8289 0.053 Uiso 1 1 calc GR . . . .
H1B H 0.7136 0.8035 0.6636 0.053 Uiso 1 1 calc GR . . . .
H1C H 0.7717 0.8447 0.7113 0.053 Uiso 1 1 calc GR . . . .
C2 C 0.88741(9) 0.81021(4) 0.60480(18) 0.0366(3) Uani 1 1 d . . . . .
H2A H 0.8904 0.8012 0.4991 0.055 Uiso 1 1 calc GR . . . .
H2B H 0.9361 0.8026 0.6626 0.055 Uiso 1 1 calc GR . . . .
H2C H 0.8782 0.8434 0.6104 0.055 Uiso 1 1 calc GR . . . .
C3 C 0.82270(8) 0.73857(4) 0.66483(13) 0.0246(3) Uani 1 1 d . . . . .
C4 C 0.76043(8) 0.71441(4) 0.71834(14) 0.0268(3) Uani 1 1 d . . . . .
H4 H 0.7185 0.7309 0.7548 0.032 Uiso 1 1 calc R . . . .
C5 C 0.75935(7) 0.66667(4) 0.71868(14) 0.0250(3) Uani 1 1 d . . . . .
H5 H 0.7169 0.6508 0.7556 0.030 Uiso 1 1 calc R . . . .
C6 C 0.81955(7) 0.64222(4) 0.66578(13) 0.0229(3) Uani 1 1 d . . . . .
C7 C 0.88195(8) 0.66516(4) 0.61408(14) 0.0262(3) Uani 1 1 d . . . . .
H7 H 0.9238 0.6482 0.5791 0.031 Uiso 1 1 calc R . . . .
C8 C 0.88366(8) 0.71284(4) 0.61313(14) 0.0270(3) Uani 1 1 d . . . . .
H8 H 0.9267 0.7283 0.5769 0.032 Uiso 1 1 calc R . . . .
C9 C 0.87206(7) 0.57008(4) 0.76823(14) 0.0238(3) Uani 1 1 d . . . . .
C10 C 0.87109(7) 0.51933(4) 0.76518(14) 0.0236(3) Uani 1 1 d . . . . .
C11 C 0.92163(8) 0.49573(5) 0.86271(15) 0.0314(3) Uani 1 1 d . . . . .
H11 H 0.9576 0.5122 0.9284 0.038 Uiso 1 1 calc R . . . .
C12 C 0.92097(8) 0.44738(5) 0.86685(16) 0.0330(3) Uani 1 1 d . . . . .
H12 H 0.9563 0.4314 0.9352 0.040 Uiso 1 1 calc R . . . .
C13 C 0.86967(8) 0.42353(4) 0.77277(15) 0.0307(3) Uani 1 1 d . . . . .
H13 H 0.8689 0.3909 0.7777 0.037 Uiso 1 1 calc R . . . .
C14 C 0.76456(9) 0.42325(5) 0.56594(15) 0.0325(3) Uani 1 1 d . . . . .
H14 H 0.7636 0.3906 0.5652 0.039 Uiso 1 1 calc R . . . .
C15 C 0.71480(9) 0.44703(5) 0.46845(15) 0.0344(3) Uani 1 1 d . . . . .
H15 H 0.6798 0.4308 0.4000 0.041 Uiso 1 1 calc R . . . .
C16 C 0.71487(8) 0.49552(5) 0.46845(14) 0.0297(3) Uani 1 1 d . . . . .
H16 H 0.6798 0.5118 0.4004 0.036 Uiso 1 1 calc R . . . .
C17 C 0.76532(7) 0.51927(4) 0.56621(13) 0.0235(3) Uani 1 1 d . . . . .
C18 C 0.81805(7) 0.49534(4) 0.66609(13) 0.0224(3) Uani 1 1 d . . . . .
C19 C 0.81758(8) 0.44645(4) 0.66802(14) 0.0265(3) Uani 1 1 d . . . . .
C20 C 0.76434(7) 0.57004(4) 0.56611(13) 0.0224(3) Uani 1 1 d . . . . .
C21 C 0.44199(10) 0.43357(5) 0.82398(19) 0.0473(4) Uani 1 1 d . . . . .
H21A H 0.4415 0.4440 0.9288 0.071 Uiso 1 1 calc GR . . . .
H21B H 0.4539 0.4006 0.8224 0.071 Uiso 1 1 calc GR . . . .
H21C H 0.3912 0.4390 0.7709 0.071 Uiso 1 1 calc GR . . . .
C22 C 0.5000 0.50611(6) 0.7500 0.0300(4) Uani 1 2 d S T P . .
C23 C 0.55404(8) 0.53114(5) 0.67426(16) 0.0318(3) Uani 1 1 d . . . . .
H23 H 0.5916 0.5152 0.6222 0.038 Uiso 1 1 calc R . . . .
C24 C 0.55362(8) 0.57892(4) 0.67400(15) 0.0289(3) Uani 1 1 d . . . . .
H24 H 0.5904 0.5953 0.6212 0.035 Uiso 1 1 calc R . . . .
C25 C 0.5000 0.60258(6) 0.7500 0.0241(4) Uani 1 2 d S T P . .
C26 C 0.55000(7) 0.67488(4) 0.85862(13) 0.0239(3) Uani 1 1 d . . . . .
C27 C 0.54628(7) 0.72559(4) 0.86175(13) 0.0229(3) Uani 1 1 d . . . . .
C28 C 0.5000 0.74960(6) 0.7500 0.0207(4) Uani 1 2 d S T P . .
C29 C 0.5000 0.79842(6) 0.7500 0.0239(4) Uani 1 2 d S T P . .
C30 C 0.54320(8) 0.82152(4) 0.86865(14) 0.0272(3) Uani 1 1 d . . . . .
H30 H 0.5424 0.8542 0.8722 0.033 Uiso 1 1 calc R . . . .
C31 C 0.58603(8) 0.79776(5) 0.97802(15) 0.0309(3) Uani 1 1 d . . . . .
H31 H 0.6141 0.8139 1.0576 0.037 Uiso 1 1 calc R . . . .
C32 C 0.58881(8) 0.74936(5) 0.97344(15) 0.0286(3) Uani 1 1 d . . . . .
H32 H 0.6202 0.7331 1.0478 0.034 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
N1 C1 1.4433(18) . ?
N1 C2 1.4433(19) . ?
N1 C3 1.3750(16) . ?
N2 C6 1.4460(15) . ?
N2 C9 1.4034(15) . ?
N2 C20 1.4065(15) . ?
N3 C21 1.4449(18) 2_656 ?
N3 C21 1.4448(18) . ?
N3 C22 1.376(2) . ?
N4 C25 1.452(2) . ?
N4 C26 1.4055(13) 2_656 ?
N4 C26 1.4054(13) . ?
O1 C9 1.2154(14) . ?
O2 C20 1.2152(14) . ?
O3 C26 1.2139(14) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.4033(19) . ?
C3 C8 1.4026(18) . ?
C4 H4 0.9500 . ?
C4 C5 1.3881(17) . ?
C5 H5 0.9500 . ?
C5 C6 1.3770(18) . ?
C6 C7 1.3815(18) . ?
C7 H7 0.9500 . ?
C7 C8 1.3862(17) . ?
C8 H8 0.9500 . ?
C9 C10 1.4753(17) . ?
C10 C11 1.3683(17) . ?
C10 C18 1.4081(17) . ?
C11 H11 0.9500 . ?
C11 C12 1.4058(18) . ?
C12 H12 0.9500 . ?
C12 C13 1.362(2) . ?
C13 H13 0.9500 . ?
C13 C19 1.4126(18) . ?
C14 H14 0.9500 . ?
C14 C15 1.363(2) . ?
C14 C19 1.4120(18) . ?
C15 H15 0.9500 . ?
C15 C16 1.4095(19) . ?
C16 H16 0.9500 . ?
C16 C17 1.3708(17) . ?
C17 C18 1.4078(17) . ?
C17 C20 1.4760(17) . ?
C18 C19 1.4213(17) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.4007(17) 2_656 ?
C22 C23 1.4007(17) . ?
C23 H23 0.9500 . ?
C23 C24 1.3889(18) . ?
C24 H24 0.9500 . ?
C24 C25 1.3765(16) . ?
C25 C24 1.3765(16) 2_656 ?
C26 C27 1.4758(17) . ?
C27 C28 1.4118(14) . ?
C27 C32 1.3756(17) . ?
C28 C27 1.4118(14) 2_656 ?
C28 C29 1.419(2) . ?
C29 C30 1.4143(15) . ?
C29 C30 1.4143(15) 2_656 ?
C30 H30 0.9500 . ?
C30 C31 1.3640(18) . ?
C31 H31 0.9500 . ?
C31 C32 1.4084(18) . ?
C32 H32 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
C1 N1 C2 119.22(11) . . ?
C3 N1 C1 120.29(12) . . ?
C3 N1 C2 120.34(11) . . ?
C9 N2 C6 117.39(9) . . ?
C9 N2 C20 124.71(10) . . ?
C20 N2 C6 117.89(9) . . ?
C21 N3 C21 119.06(18) . 2_656 ?
C22 N3 C21 120.47(9) . . ?
C22 N3 C21 120.47(9) . 2_656 ?
C26 N4 C25 117.53(7) . . ?
C26 N4 C25 117.53(7) 2_656 . ?
C26 N4 C26 124.94(14) . 2_656 ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 C4 121.05(12) . . ?
N1 C3 C8 121.17(12) . . ?
C8 C3 C4 117.76(11) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.79(12) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.29(12) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 N2 120.42(11) . . ?
C5 C6 C7 120.07(12) . . ?
C7 C6 N2 119.51(11) . . ?
C6 C7 H7 119.9 . . ?
C6 C7 C8 120.15(12) . . ?
C8 C7 H7 119.9 . . ?
C3 C8 H8 119.5 . . ?
C7 C8 C3 120.93(12) . . ?
C7 C8 H8 119.5 . . ?
N2 C9 C10 116.50(10) . . ?
O1 C9 N2 120.54(11) . . ?
O1 C9 C10 122.96(11) . . ?
C11 C10 C9 118.95(11) . . ?
C11 C10 C18 120.20(12) . . ?
C18 C10 C9 120.84(11) . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.78(12) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 119.93(12) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.4 . . ?
C12 C13 C19 121.21(12) . . ?
C19 C13 H13 119.4 . . ?
C15 C14 H14 119.5 . . ?
C15 C14 C19 120.99(12) . . ?
C19 C14 H14 119.5 . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.45(12) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.27(12) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C18 120.14(12) . . ?
C16 C17 C20 119.76(11) . . ?
C18 C17 C20 120.09(11) . . ?
C10 C18 C19 119.46(11) . . ?
C17 C18 C10 120.69(11) . . ?
C17 C18 C19 119.84(11) . . ?
C13 C19 C18 118.39(11) . . ?
C14 C19 C13 123.33(12) . . ?
C14 C19 C18 118.28(11) . . ?
N2 C20 C17 117.14(10) . . ?
O2 C20 N2 120.18(11) . . ?
O2 C20 C17 122.68(11) . . ?
N3 C21 H21A 109.5 . . ?
N3 C21 H21B 109.5 . . ?
N3 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N3 C22 C23 121.30(8) . . ?
N3 C22 C23 121.30(8) . 2_656 ?
C23 C22 C23 117.40(17) . 2_656 ?
C22 C23 H23 119.4 . . ?
C24 C23 C22 121.11(13) . . ?
C24 C23 H23 119.4 . . ?
C23 C24 H24 119.9 . . ?
C25 C24 C23 120.17(13) . . ?
C25 C24 H24 119.9 . . ?
C24 C25 N4 119.98(8) 2_656 . ?
C24 C25 N4 119.98(8) . . ?
C24 C25 C24 120.04(17) . 2_656 ?
N4 C26 C27 116.68(10) . . ?
O3 C26 N4 120.15(11) . . ?
O3 C26 C27 123.17(11) . . ?
C28 C27 C26 120.26(11) . . ?
C32 C27 C26 119.57(11) . . ?
C32 C27 C28 120.16(12) . . ?
C27 C28 C27 120.73(15) . 2_656 ?
C27 C28 C29 119.63(8) . . ?
C27 C28 C29 119.64(8) 2_656 . ?
C30 C29 C28 118.35(8) . . ?
C30 C29 C28 118.34(8) 2_656 . ?
C30 C29 C30 123.31(16) 2_656 . ?
C29 C30 H30 119.4 . . ?
C31 C30 C29 121.19(12) . . ?
C31 C30 H30 119.4 . . ?
C30 C31 H31 119.9 . . ?
C30 C31 C32 120.22(11) . . ?
C32 C31 H31 119.9 . . ?
C27 C32 C31 120.33(12) . . ?
C27 C32 H32 119.8 . . ?
C31 C32 H32 119.8 . . ?

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
N1 C3 C4 C5 -178.64(11) . . . . ?
N1 C3 C8 C7 178.61(11) . . . . ?
N2 C6 C7 C8 -179.85(11) . . . . ?
N2 C9 C10 C11 -179.62(11) . . . . ?
N2 C9 C10 C18 -0.99(17) . . . . ?
N3 C22 C23 C24 179.72(9) . . . . ?
N4 C26 C27 C28 -6.18(16) . . . . ?
N4 C26 C27 C32 174.46(11) . . . . ?
O1 C9 C10 C11 0.0(2) . . . . ?
O1 C9 C10 C18 178.59(12) . . . . ?
O3 C26 C27 C28 173.85(11) . . . . ?
O3 C26 C27 C32 -5.5(2) . . . . ?
C1 N1 C3 C4 -1.28(17) . . . . ?
C1 N1 C3 C8 -179.39(11) . . . . ?
C2 N1 C3 C4 -176.92(11) . . . . ?
C2 N1 C3 C8 4.97(17) . . . . ?
C3 C4 C5 C6 -0.22(18) . . . . ?
C4 C3 C8 C7 0.44(17) . . . . ?
C4 C5 C6 N2 179.81(10) . . . . ?
C4 C5 C6 C7 0.95(17) . . . . ?
C5 C6 C7 C8 -0.97(18) . . . . ?
C6 N2 C9 O1 1.43(18) . . . . ?
C6 N2 C9 C10 -178.98(11) . . . . ?
C6 N2 C20 O2 -1.51(17) . . . . ?
C6 N2 C20 C17 178.83(10) . . . . ?
C6 C7 C8 C3 0.27(18) . . . . ?
C8 C3 C4 C5 -0.47(17) . . . . ?
C9 N2 C6 C5 -110.47(13) . . . . ?
C9 N2 C6 C7 68.40(15) . . . . ?
C9 N2 C20 O2 178.07(11) . . . . ?
C9 N2 C20 C17 -1.59(17) . . . . ?
C9 C10 C11 C12 177.98(12) . . . . ?
C9 C10 C18 C17 0.81(18) . . . . ?
C9 C10 C18 C19 -178.77(11) . . . . ?
C10 C11 C12 C13 0.1(2) . . . . ?
C10 C18 C19 C13 1.46(18) . . . . ?
C10 C18 C19 C14 -179.09(11) . . . . ?
C11 C10 C18 C17 179.43(12) . . . . ?
C11 C10 C18 C19 -0.15(19) . . . . ?
C11 C12 C13 C19 1.3(2) . . . . ?
C12 C13 C19 C14 178.54(13) . . . . ?
C12 C13 C19 C18 -2.03(19) . . . . ?
C14 C15 C16 C17 0.3(2) . . . . ?
C15 C14 C19 C13 179.12(13) . . . . ?
C15 C14 C19 C18 -0.30(19) . . . . ?
C15 C16 C17 C18 0.74(19) . . . . ?
C15 C16 C17 C20 -179.44(12) . . . . ?
C16 C17 C18 C10 178.86(12) . . . . ?
C16 C17 C18 C19 -1.56(18) . . . . ?
C16 C17 C20 N2 -178.53(11) . . . . ?
C16 C17 C20 O2 1.81(19) . . . . ?
C17 C18 C19 C13 -178.12(11) . . . . ?
C17 C18 C19 C14 1.33(18) . . . . ?
C18 C10 C11 C12 -0.7(2) . . . . ?
C18 C17 C20 N2 1.29(17) . . . . ?
C18 C17 C20 O2 -178.36(12) . . . . ?
C19 C14 C15 C16 -0.5(2) . . . . ?
C20 N2 C6 C5 69.14(14) . . . . ?
C20 N2 C6 C7 -111.99(13) . . . . ?
C20 N2 C9 O1 -178.15(12) . . . . ?
C20 N2 C9 C10 1.43(17) . . . . ?
C20 C17 C18 C10 -0.96(18) . . . . ?
C20 C17 C18 C19 178.61(11) . . . . ?
C21 N3 C22 C23 -177.66(9) 2_656 . . 2_656 ?
C21 N3 C22 C23 2.34(9) . . . 2_656 ?
C21 N3 C22 C23 2.34(9) 2_656 . . . ?
C21 N3 C22 C23 -177.66(9) . . . . ?
C22 C23 C24 C25 0.56(18) . . . . ?
C23 C22 C23 C24 -0.28(9) 2_656 . . . ?
C23 C24 C25 N4 179.72(9) . . . . ?
C23 C24 C25 C24 -0.28(9) . . . 2_656 ?
C25 N4 C26 O3 2.98(14) . . . . ?
C25 N4 C26 C27 -176.99(8) . . . . ?
C26 N4 C25 C24 95.15(9) . . . 2_656 ?
C26 N4 C25 C24 95.15(9) 2_656 . . . ?
C26 N4 C25 C24 -84.85(9) 2_656 . . 2_656 ?
C26 N4 C25 C24 -84.85(9) . . . . ?
C26 N4 C26 O3 -177.02(14) 2_656 . . . ?
C26 N4 C26 C27 3.00(8) 2_656 . . . ?
C26 C27 C28 C27 3.16(8) . . . 2_656 ?
C26 C27 C28 C29 -176.84(8) . . . . ?
C26 C27 C32 C31 179.92(12) . . . . ?
C27 C28 C29 C30 -3.83(8) . . . . ?
C27 C28 C29 C30 176.17(8) 2_656 . . . ?
C27 C28 C29 C30 176.17(8) . . . 2_656 ?
C27 C28 C29 C30 -3.83(8) 2_656 . . 2_656 ?
C28 C27 C32 C31 0.56(19) . . . . ?
C28 C29 C30 C31 2.16(14) . . . . ?
C29 C30 C31 C32 0.9(2) . . . . ?
C30 C29 C30 C31 -177.84(14) 2_656 . . . ?
C30 C31 C32 C27 -2.3(2) . . . . ?
C32 C27 C28 C27 -177.49(14) . . . 2_656 ?
C32 C27 C28 C29 2.51(14) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_original_sample_id acb134
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Vapour Deposition'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_GDMIM
_database_code_depnum_ccdc_archive 'CCDC 1003613'
_audit_update_record             
;
2015-01-16 deposited with the CCDC.
2015-04-20 downloaded from the CCDC.
;
_audit_creation_date             2015-01-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.09 svn.r3130 for OlexSys, GUI svn.r4987)
;
_chemical_name_common            ?
_chemical_name_systematic        N,N-dimethylaniline-N-naphthalimide
_chemical_formula_moiety         'C20 H16 N2 O2'
_chemical_formula_sum            'C20 H16 N2 O2'
_chemical_formula_weight         316.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H16 N2 O2'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4336(8)
_cell_length_b                   9.5749(8)
_cell_length_c                   9.9183(9)
_cell_angle_alpha                115.803(9)
_cell_angle_beta                 97.324(7)
_cell_angle_gamma                104.839(7)
_cell_volume                     749.69(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2145
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      28.5798
_cell_measurement_theta_min      3.2314
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.973
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98674
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.802
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5582
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.802
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.643
_diffrn_reflns_theta_min         3.238
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.802
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -37.00   59.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.2632   77.0000 -150.0000 96

#__ type_ start__ end____ width___ exp.time_
  2 omega  -17.00   81.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038   77.0000    0.0000 98

#__ type_ start__ end____ width___ exp.time_
  3 omega   -6.00   83.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038   77.0000  120.0000 89
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0014881000
_diffrn_orient_matrix_UB_12      0.0030572000
_diffrn_orient_matrix_UB_13      -0.0700046000
_diffrn_orient_matrix_UB_21      0.0420281000
_diffrn_orient_matrix_UB_22      -0.0543741000
_diffrn_orient_matrix_UB_23      -0.0189211000
_diffrn_orient_matrix_UB_31      -0.0691008000
_diffrn_orient_matrix_UB_32      -0.0688718000
_diffrn_orient_matrix_UB_33      -0.0395688000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2392
_reflns_number_total             3090
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_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 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_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    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3090
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0449
_refine_ls_restrained_S_all      1.029
_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)+(0.0542P)²+0.2698P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1255
_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,H,H,H) groups
2. Others
 Fixed Sof: H19A(0.5) H19B(0.5) H19C(0.5) H19D(0.5) H19E(0.5) H19F(0.5)
 H20A(0.5) H20B(0.5) H20C(0.5) H20D(0.5) H20E(0.5) H20F(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C13(H13), C14(H14), C16(H16),
 C17(H17)
3.b Disordered Me refined with riding coordinates:
 C19(H19A,H19B,H19C,H19D,H19E,H19F), C20(H20A,H20B,H20C,H20D,H20E,H20F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O1 O 0.25450(12) 0.66487(13) 0.28679(13) 0.0268(3) Uani 1 1 d . . . . .
O2 O -0.15781(12) 0.24728(14) 0.22209(15) 0.0307(3) Uani 1 1 d . . . . .
N1 N 0.04762(13) 0.45361(15) 0.24946(14) 0.0188(3) Uani 1 1 d . . . . .
N2 N -0.32148(15) 0.83405(17) 0.25520(15) 0.0258(3) Uani 1 1 d . . . . .
C1 C 0.20408(16) 0.52729(18) 0.27256(17) 0.0191(3) Uani 1 1 d . . . . .
C2 C 0.30077(16) 0.42857(18) 0.27597(17) 0.0186(3) Uani 1 1 d . . . . .
C3 C 0.45570(17) 0.49579(19) 0.30321(18) 0.0219(3) Uani 1 1 d . . . . .
H3 H 0.5001 0.6063 0.3234 0.026 Uiso 1 1 calc R . . . .
C4 C 0.54887(17) 0.4018(2) 0.30141(19) 0.0249(4) Uani 1 1 d . . . . .
H4 H 0.6559 0.4492 0.3208 0.030 Uiso 1 1 calc R . . . .
C5 C 0.48590(17) 0.2424(2) 0.27178(18) 0.0240(4) Uani 1 1 d . . . . .
H5 H 0.5500 0.1800 0.2701 0.029 Uiso 1 1 calc R . . . .
C6 C 0.32712(17) 0.16866(19) 0.24361(17) 0.0205(3) Uani 1 1 d . . . . .
C7 C 0.25666(18) 0.00441(19) 0.21265(18) 0.0238(3) Uani 1 1 d . . . . .
H7 H 0.3174 -0.0616 0.2095 0.029 Uiso 1 1 calc R . . . .
C8 C 0.10268(18) -0.06101(19) 0.18724(18) 0.0244(4) Uani 1 1 d . . . . .
H8 H 0.0576 -0.1718 0.1661 0.029 Uiso 1 1 calc R . . . .
C9 C 0.01062(17) 0.03503(19) 0.19221(17) 0.0221(3) Uani 1 1 d . . . . .
H9 H -0.0962 -0.0109 0.1752 0.026 Uiso 1 1 calc R . . . .
C10 C 0.07482(16) 0.19488(18) 0.22159(17) 0.0183(3) Uani 1 1 d . . . . .
C11 C 0.23350(16) 0.26514(18) 0.24726(16) 0.0177(3) Uani 1 1 d . . . . .
C12 C -0.02328(16) 0.29517(19) 0.22999(17) 0.0202(3) Uani 1 1 d . . . . .
C13 C -0.23731(16) 0.60490(18) 0.11433(17) 0.0201(3) Uani 1 1 d . . . . .
H13 H -0.3045 0.5769 0.0193 0.024 Uiso 1 1 calc R . . . .
C14 C -0.14547(16) 0.51268(18) 0.11312(17) 0.0204(3) Uani 1 1 d . . . . .
H14 H -0.1493 0.4231 0.0176 0.024 Uiso 1 1 calc R . . . .
C15 C -0.04810(16) 0.55045(18) 0.25049(17) 0.0186(3) Uani 1 1 d . . . . .
C16 C -0.04369(17) 0.68008(19) 0.38883(18) 0.0216(3) Uani 1 1 d . . . . .
H16 H 0.0224 0.7053 0.4834 0.026 Uiso 1 1 calc R . . . .
C17 C -0.13424(17) 0.77371(19) 0.39168(18) 0.0216(3) Uani 1 1 d . . . . .
H17 H -0.1296 0.8625 0.4882 0.026 Uiso 1 1 calc R . . . .
C18 C -0.23299(16) 0.73945(18) 0.25387(17) 0.0187(3) Uani 1 1 d . . . . .
C19 C -0.3325(2) 0.9573(2) 0.3993(2) 0.0311(4) Uani 1 1 d . . . . .
H19A H -0.4002 1.0114 0.3767 0.047 Uiso 0.5 1 calc R . P . .
H19B H -0.3737 0.9043 0.4578 0.047 Uiso 0.5 1 calc R . P . .
H19C H -0.2309 1.0401 0.4612 0.047 Uiso 0.5 1 calc R . P . .
H19D H -0.2697 0.9591 0.4871 0.047 Uiso 0.5 1 calc R . P . .
H19E H -0.2961 1.0663 0.4060 0.047 Uiso 0.5 1 calc R . P . .
H19F H -0.4390 0.9304 0.4026 0.047 Uiso 0.5 1 calc R . P . .
C20 C -0.41784(19) 0.8017(2) 0.1118(2) 0.0311(4) Uani 1 1 d . . . . .
H20A H -0.4720 0.8805 0.1350 0.047 Uiso 0.5 1 calc R . P . .
H20B H -0.3549 0.8139 0.0436 0.047 Uiso 0.5 1 calc R . P . .
H20C H -0.4919 0.6886 0.0597 0.047 Uiso 0.5 1 calc R . P . .
H20D H -0.4072 0.7082 0.0239 0.047 Uiso 0.5 1 calc R . P . .
H20E H -0.5243 0.7748 0.1153 0.047 Uiso 0.5 1 calc R . P . .
H20F H -0.3874 0.9001 0.0991 0.047 Uiso 0.5 1 calc R . P . .


_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 C1 1.2172(18) . ?
O2 C12 1.2133(18) . ?
N1 C1 1.4031(19) . ?
N1 C12 1.4066(19) . ?
N1 C15 1.4486(17) . ?
N2 C18 1.3773(18) . ?
N2 C19 1.441(2) . ?
N2 C20 1.444(2) . ?
C1 C2 1.479(2) . ?
C2 C3 1.375(2) . ?
C2 C11 1.411(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.407(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.367(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.414(2) . ?
C6 C7 1.415(2) . ?
C6 C11 1.425(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.367(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.408(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.373(2) . ?
C10 C11 1.413(2) . ?
C10 C12 1.4801(19) . ?
C13 H13 0.9500 . ?
C13 C14 1.384(2) . ?
C13 C18 1.408(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.383(2) . ?
C15 C16 1.379(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.382(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.404(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C19 H19D 0.9800 . ?
C19 H19E 0.9800 . ?
C19 H19F 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C20 H20D 0.9800 . ?
C20 H20E 0.9800 . ?
C20 H20F 0.9800 . ?

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
C1 N1 C12 125.32(12) . . ?
C1 N1 C15 117.39(12) . . ?
C12 N1 C15 117.27(12) . . ?
C18 N2 C19 121.35(13) . . ?
C18 N2 C20 120.73(13) . . ?
C19 N2 C20 117.66(13) . . ?
O1 C1 N1 120.41(13) . . ?
O1 C1 C2 122.94(13) . . ?
N1 C1 C2 116.64(12) . . ?
C3 C2 C1 119.50(13) . . ?
C3 C2 C11 120.45(13) . . ?
C11 C2 C1 120.03(13) . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.34(14) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.22(14) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.27(14) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C7 123.37(14) . . ?
C5 C6 C11 118.24(14) . . ?
C7 C6 C11 118.38(13) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 C6 121.20(14) . . ?
C8 C7 H7 119.4 . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.30(14) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.19(14) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 C11 120.65(13) . . ?
C9 C10 C12 119.40(13) . . ?
C11 C10 C12 119.94(13) . . ?
C2 C11 C6 119.47(13) . . ?
C2 C11 C10 121.26(13) . . ?
C10 C11 C6 119.27(13) . . ?
O2 C12 N1 120.25(13) . . ?
O2 C12 C10 123.25(14) . . ?
N1 C12 C10 116.50(12) . . ?
C14 C13 H13 119.4 . . ?
C14 C13 C18 121.20(14) . . ?
C18 C13 H13 119.4 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.24(14) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 N1 120.30(13) . . ?
C16 C15 N1 120.14(13) . . ?
C16 C15 C14 119.56(13) . . ?
C15 C16 H16 119.6 . . ?
C15 C16 C17 120.82(14) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 H17 119.5 . . ?
C16 C17 C18 120.91(14) . . ?
C18 C17 H17 119.5 . . ?
N2 C18 C13 121.42(13) . . ?
N2 C18 C17 121.32(13) . . ?
C17 C18 C13 117.26(13) . . ?
N2 C19 H19A 109.5 . . ?
N2 C19 H19B 109.5 . . ?
N2 C19 H19C 109.5 . . ?
N2 C19 H19D 109.5 . . ?
N2 C19 H19E 109.5 . . ?
N2 C19 H19F 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19A C19 H19D 141.1 . . ?
H19A C19 H19E 56.3 . . ?
H19A C19 H19F 56.3 . . ?
H19B C19 H19C 109.5 . . ?
H19B C19 H19D 56.3 . . ?
H19B C19 H19E 141.1 . . ?
H19B C19 H19F 56.3 . . ?
H19C C19 H19D 56.3 . . ?
H19C C19 H19E 56.3 . . ?
H19C C19 H19F 141.1 . . ?
H19D C19 H19E 109.5 . . ?
H19D C19 H19F 109.5 . . ?
H19E C19 H19F 109.5 . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
N2 C20 H20D 109.5 . . ?
N2 C20 H20E 109.5 . . ?
N2 C20 H20F 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20A C20 H20D 141.1 . . ?
H20A C20 H20E 56.3 . . ?
H20A C20 H20F 56.3 . . ?
H20B C20 H20C 109.5 . . ?
H20B C20 H20D 56.3 . . ?
H20B C20 H20E 141.1 . . ?
H20B C20 H20F 56.3 . . ?
H20C C20 H20D 56.3 . . ?
H20C C20 H20E 56.3 . . ?
H20C C20 H20F 141.1 . . ?
H20D C20 H20E 109.5 . . ?
H20D C20 H20F 109.5 . . ?
H20E C20 H20F 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
O1 C1 C2 C3 3.0(2) . . . . ?
O1 C1 C2 C11 -175.29(13) . . . . ?
N1 C1 C2 C3 -177.90(13) . . . . ?
N1 C1 C2 C11 3.8(2) . . . . ?
N1 C15 C16 C17 179.94(13) . . . . ?
C1 N1 C12 O2 174.59(14) . . . . ?
C1 N1 C12 C10 -4.9(2) . . . . ?
C1 N1 C15 C14 106.90(16) . . . . ?
C1 N1 C15 C16 -73.70(18) . . . . ?
C1 C2 C3 C4 -177.74(13) . . . . ?
C1 C2 C11 C6 177.06(13) . . . . ?
C1 C2 C11 C10 -2.8(2) . . . . ?
C2 C3 C4 C5 0.3(2) . . . . ?
C3 C2 C11 C6 -1.2(2) . . . . ?
C3 C2 C11 C10 178.93(13) . . . . ?
C3 C4 C5 C6 -0.5(2) . . . . ?
C4 C5 C6 C7 -179.91(15) . . . . ?
C4 C5 C6 C11 -0.2(2) . . . . ?
C5 C6 C7 C8 179.52(15) . . . . ?
C5 C6 C11 C2 1.0(2) . . . . ?
C5 C6 C11 C10 -179.14(13) . . . . ?
C6 C7 C8 C9 -0.3(2) . . . . ?
C7 C6 C11 C2 -179.22(13) . . . . ?
C7 C6 C11 C10 0.6(2) . . . . ?
C7 C8 C9 C10 0.5(2) . . . . ?
C8 C9 C10 C11 0.0(2) . . . . ?
C8 C9 C10 C12 -178.58(13) . . . . ?
C9 C10 C11 C2 179.34(13) . . . . ?
C9 C10 C11 C6 -0.5(2) . . . . ?
C9 C10 C12 O2 4.9(2) . . . . ?
C9 C10 C12 N1 -175.66(13) . . . . ?
C11 C2 C3 C4 0.6(2) . . . . ?
C11 C6 C7 C8 -0.2(2) . . . . ?
C11 C10 C12 O2 -173.65(14) . . . . ?
C11 C10 C12 N1 5.8(2) . . . . ?
C12 N1 C1 O1 179.30(13) . . . . ?
C12 N1 C1 C2 0.2(2) . . . . ?
C12 N1 C15 C14 -74.94(17) . . . . ?
C12 N1 C15 C16 104.46(16) . . . . ?
C12 C10 C11 C2 -2.1(2) . . . . ?
C12 C10 C11 C6 178.04(13) . . . . ?
C13 C14 C15 N1 179.75(13) . . . . ?
C13 C14 C15 C16 0.3(2) . . . . ?
C14 C13 C18 N2 178.43(13) . . . . ?
C14 C13 C18 C17 -1.3(2) . . . . ?
C14 C15 C16 C17 -0.7(2) . . . . ?
C15 N1 C1 O1 -2.7(2) . . . . ?
C15 N1 C1 C2 178.19(12) . . . . ?
C15 N1 C12 O2 -3.4(2) . . . . ?
C15 N1 C12 C10 177.13(12) . . . . ?
C15 C16 C17 C18 0.0(2) . . . . ?
C16 C17 C18 N2 -178.74(14) . . . . ?
C16 C17 C18 C13 1.0(2) . . . . ?
C18 C13 C14 C15 0.7(2) . . . . ?
C19 N2 C18 C13 171.67(14) . . . . ?
C19 N2 C18 C17 -8.6(2) . . . . ?
C20 N2 C18 C13 -2.3(2) . . . . ?
C20 N2 C18 C17 177.42(14) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_original_sample_id G-DIMM
_olex2_submission_special_instructions 'No special instructions were received'
