# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# 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_ra2
_database_code_depnum_ccdc_archive 'CCDC 1848302'
_audit_update_record             
;
2018-06-09 deposited with the CCDC.
2018-09-17 downloaded from the CCDC.
;

_audit_creation_date             2018-05-16
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.01.05 svn.r3372 for Rigaku Oxford Diffraction, GUI svn.r5289)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
; 
1-amino-4-(3,4,5-trimethoxyphenyl)imidazo[1,2-a]quinoxaline-2-carbonitrile 
;
_chemical_name_common            imidazo[1,2-a]quinoxaline
_chemical_melting_point          457
_chemical_formula_moiety         'C20 H17 N5 O3'
_chemical_formula_sum            'C20 H17 N5 O3'
_chemical_formula_weight         375.39

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           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

loop_
_symmetry_equiv_pos_as_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                   4.7930(2)
_cell_length_b                   16.5650(8)
_cell_length_c                   23.2081(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.619(5)
_cell_angle_gamma                90.00
_cell_volume                     1836.65(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1937
_cell_measurement_theta_max      29.0560
_cell_measurement_theta_min      4.4200

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62432
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4324
_diffrn_detector_type            Atlas

_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4390
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.52
_diffrn_reflns_theta_max         29.46
_reflns_number_total             2942
_reflns_number_gt                2665

_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'

_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)+(0.1000P)²+0.3129P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 735 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(13)
_refine_ls_number_reflns         2942
_refine_ls_number_parameters     264
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1219
_refine_ls_wR_factor_gt          0.1151
_refine_ls_goodness_of_fit_ref   0.878
_refine_ls_restrained_S_all      0.878
_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
C1 C -0.1983(6) 0.02529(16) 0.46412(12) 0.0505(6) Uani 1 1 d . . .
H1 H -0.2890 0.0221 0.4980 0.061 Uiso 1 1 calc R . .
C2 C -0.2585(6) -0.03031(17) 0.42127(13) 0.0556(7) Uani 1 1 d . . .
H2 H -0.3890 -0.0708 0.4261 0.067 Uiso 1 1 calc R . .
C3 C -0.1246(6) -0.02594(17) 0.37080(13) 0.0558(7) Uani 1 1 d . . .
H3 H -0.1628 -0.0645 0.3421 0.067 Uiso 1 1 calc R . .
C4 C 0.0654(6) 0.03487(16) 0.36232(11) 0.0478(6) Uani 1 1 d . . .
H4 H 0.1548 0.0373 0.3283 0.057 Uiso 1 1 calc R . .
C5 C 0.1212(5) 0.09255(13) 0.40546(10) 0.0374(5) Uani 1 1 d . . .
C6 C -0.0032(5) 0.08686(14) 0.45798(10) 0.0394(5) Uani 1 1 d . . .
C7 C 0.4537(5) 0.18482(14) 0.35657(10) 0.0373(5) Uani 1 1 d . . .
C8 C 0.6160(5) 0.24667(14) 0.38021(10) 0.0399(5) Uani 1 1 d . . .
C9 C 0.3864(4) 0.20686(13) 0.44959(9) 0.0361(5) Uani 1 1 d . . .
C10 C 0.2504(5) 0.19316(14) 0.50237(10) 0.0375(5) Uani 1 1 d . . .
C11 C 0.8053(6) 0.29254(16) 0.34862(11) 0.0476(6) Uani 1 1 d . . .
C12 C 0.3125(5) 0.24265(14) 0.55559(9) 0.0386(5) Uani 1 1 d . . .
C13 C 0.4942(5) 0.30774(17) 0.55872(10) 0.0436(5) Uani 1 1 d . . .
H13 H 0.5915 0.3212 0.5270 0.052 Uiso 1 1 calc R . .
C14 C 0.5314(5) 0.35297(15) 0.60906(10) 0.0422(5) Uani 1 1 d . . .
C15 C 0.3854(5) 0.33259(15) 0.65721(10) 0.0413(5) Uani 1 1 d . . .
C16 C 0.2090(5) 0.26665(15) 0.65389(10) 0.0410(5) Uani 1 1 d . . .
C17 C 0.1710(5) 0.22166(15) 0.60369(10) 0.0426(5) Uani 1 1 d . . .
H17 H 0.0511 0.1774 0.6020 0.051 Uiso 1 1 calc R . .
C18 C 0.8492(6) 0.4439(2) 0.56886(13) 0.0585(7) Uani 1 1 d . . .
H18A H 0.9803 0.4026 0.5603 0.088 Uiso 1 1 calc R . .
H18B H 0.9482 0.4931 0.5785 0.088 Uiso 1 1 calc R . .
H18C H 0.7199 0.4526 0.5357 0.088 Uiso 1 1 calc R . .
C19 C 0.2965(8) 0.45357(18) 0.70626(12) 0.0641(8) Uani 1 1 d . . .
H19A H 0.3758 0.4857 0.6773 0.096 Uiso 1 1 calc R . .
H19B H 0.3295 0.4794 0.7432 0.096 Uiso 1 1 calc R . .
H19C H 0.0986 0.4481 0.6969 0.096 Uiso 1 1 calc R . .
C20 C -0.0905(8) 0.1797(2) 0.70329(14) 0.0673(9) Uani 1 1 d . . .
H20A H -0.2245 0.1792 0.6702 0.101 Uiso 1 1 calc R . .
H20B H -0.1870 0.1783 0.7380 0.101 Uiso 1 1 calc R . .
H20C H 0.0293 0.1334 0.7022 0.101 Uiso 1 1 calc R . .
H3A H 0.536(7) 0.1812(19) 0.2813(15) 0.058(9) Uiso 1 1 d . . .
H3B H 0.255(9) 0.144(3) 0.281(2) 0.099(14) Uiso 1 1 d . . .
N1 N 0.0633(4) 0.13669(13) 0.50477(8) 0.0430(5) Uani 1 1 d . . .
N2 N 0.3076(4) 0.15749(11) 0.40166(8) 0.0357(4) Uani 1 1 d . . .
N3 N 0.4327(5) 0.15173(14) 0.30210(9) 0.0480(5) Uani 1 1 d . . .
N4 N 0.9539(6) 0.3272(2) 0.32165(12) 0.0718(8) Uani 1 1 d . . .
N5 N 0.5756(4) 0.26030(12) 0.43739(9) 0.0412(5) Uani 1 1 d . . .
O1 O 0.7004(5) 0.41925(13) 0.61629(9) 0.0608(5) Uani 1 1 d . . .
O2 O 0.4229(4) 0.37602(11) 0.70831(7) 0.0489(4) Uani 1 1 d . . .
O3 O 0.0726(4) 0.25098(12) 0.70260(8) 0.0556(5) Uani 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 C2 1.369(4) . ?
C1 C6 1.399(3) . ?
C2 C3 1.382(4) . ?
C3 C4 1.382(4) . ?
C4 C5 1.394(3) . ?
C5 C6 1.402(3) . ?
C5 N2 1.406(3) . ?
C6 N1 1.381(3) . ?
C7 C8 1.374(3) . ?
C7 N3 1.374(3) . ?
C7 N2 1.381(3) . ?
C8 N5 1.375(3) . ?
C8 C11 1.430(3) . ?
C9 N5 1.314(3) . ?
C9 N2 1.408(3) . ?
C9 C10 1.451(3) . ?
C10 N1 1.300(3) . ?
C10 C12 1.492(3) . ?
C11 N4 1.140(4) . ?
C12 C13 1.384(3) . ?
C12 C17 1.396(3) . ?
C13 C14 1.387(3) . ?
C14 O1 1.367(3) . ?
C14 C15 1.407(3) . ?
C15 C16 1.380(3) . ?
C15 O2 1.386(3) . ?
C16 O3 1.375(3) . ?
C16 C17 1.383(3) . ?
C18 O1 1.419(3) . ?
C19 O2 1.419(4) . ?
C20 O3 1.417(4) . ?

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 C1 C6 121.3(3) . . ?
C1 C2 C3 119.7(2) . . ?
C2 C3 C4 121.0(3) . . ?
C3 C4 C5 119.2(2) . . ?
C4 C5 C6 120.5(2) . . ?
C4 C5 N2 124.4(2) . . ?
C6 C5 N2 115.02(19) . . ?
N1 C6 C1 118.0(2) . . ?
N1 C6 C5 123.8(2) . . ?
C1 C6 C5 118.2(2) . . ?
C8 C7 N3 131.5(2) . . ?
C8 C7 N2 104.31(19) . . ?
N3 C7 N2 124.2(2) . . ?
C7 C8 N5 112.9(2) . . ?
C7 C8 C11 123.6(2) . . ?
N5 C8 C11 123.5(2) . . ?
N5 C9 N2 111.51(19) . . ?
N5 C9 C10 130.7(2) . . ?
N2 C9 C10 117.79(19) . . ?
N1 C10 C9 120.5(2) . . ?
N1 C10 C12 116.88(19) . . ?
C9 C10 C12 122.7(2) . . ?
N4 C11 C8 177.4(3) . . ?
C13 C12 C17 119.8(2) . . ?
C13 C12 C10 123.6(2) . . ?
C17 C12 C10 116.6(2) . . ?
C12 C13 C14 120.2(2) . . ?
O1 C14 C13 124.9(2) . . ?
O1 C14 C15 115.0(2) . . ?
C13 C14 C15 120.1(2) . . ?
C16 C15 O2 119.7(2) . . ?
C16 C15 C14 119.2(2) . . ?
O2 C15 C14 121.1(2) . . ?
O3 C16 C15 115.7(2) . . ?
O3 C16 C17 123.5(2) . . ?
C15 C16 C17 120.8(2) . . ?
C16 C17 C12 120.0(2) . . ?
C10 N1 C6 120.8(2) . . ?
C7 N2 C5 131.44(19) . . ?
C7 N2 C9 106.76(19) . . ?
C5 N2 C9 121.76(17) . . ?
C9 N5 C8 104.52(19) . . ?
C14 O1 C18 117.8(2) . . ?
C15 O2 C19 114.54(19) . . ?
C16 O3 C20 117.8(2) . . ?

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
C6 C1 C2 C3 0.0(5) . . . . ?
C1 C2 C3 C4 -1.4(5) . . . . ?
C2 C3 C4 C5 -0.1(4) . . . . ?
C3 C4 C5 C6 3.1(4) . . . . ?
C3 C4 C5 N2 -179.4(2) . . . . ?
C2 C1 C6 N1 -174.9(3) . . . . ?
C2 C1 C6 C5 2.8(4) . . . . ?
C4 C5 C6 N1 173.2(2) . . . . ?
N2 C5 C6 N1 -4.6(3) . . . . ?
C4 C5 C6 C1 -4.4(3) . . . . ?
N2 C5 C6 C1 177.9(2) . . . . ?
N3 C7 C8 N5 -179.1(2) . . . . ?
N2 C7 C8 N5 -1.0(3) . . . . ?
N3 C7 C8 C11 1.4(4) . . . . ?
N2 C7 C8 C11 179.5(2) . . . . ?
N5 C9 C10 N1 179.0(2) . . . . ?
N2 C9 C10 N1 0.3(3) . . . . ?
N5 C9 C10 C12 -0.1(4) . . . . ?
N2 C9 C10 C12 -178.8(2) . . . . ?
C7 C8 C11 N4 -5(8) . . . . ?
N5 C8 C11 N4 176(100) . . . . ?
N1 C10 C12 C13 -176.2(2) . . . . ?
C9 C10 C12 C13 3.0(4) . . . . ?
N1 C10 C12 C17 2.3(3) . . . . ?
C9 C10 C12 C17 -178.6(2) . . . . ?
C17 C12 C13 C14 -1.3(4) . . . . ?
C10 C12 C13 C14 177.1(2) . . . . ?
C12 C13 C14 O1 -178.5(3) . . . . ?
C12 C13 C14 C15 0.2(4) . . . . ?
O1 C14 C15 C16 179.8(2) . . . . ?
C13 C14 C15 C16 1.0(4) . . . . ?
O1 C14 C15 O2 -2.3(4) . . . . ?
C13 C14 C15 O2 178.9(2) . . . . ?
O2 C15 C16 O3 2.5(3) . . . . ?
C14 C15 C16 O3 -179.6(2) . . . . ?
O2 C15 C16 C17 -179.1(2) . . . . ?
C14 C15 C16 C17 -1.2(4) . . . . ?
O3 C16 C17 C12 178.5(2) . . . . ?
C15 C16 C17 C12 0.2(4) . . . . ?
C13 C12 C17 C16 1.1(3) . . . . ?
C10 C12 C17 C16 -177.5(2) . . . . ?
C9 C10 N1 C6 2.2(3) . . . . ?
C12 C10 N1 C6 -178.6(2) . . . . ?
C1 C6 N1 C10 177.6(2) . . . . ?
C5 C6 N1 C10 0.0(3) . . . . ?
C8 C7 N2 C5 -175.8(2) . . . . ?
N3 C7 N2 C5 2.4(4) . . . . ?
C8 C7 N2 C9 1.7(2) . . . . ?
N3 C7 N2 C9 -180.0(2) . . . . ?
C4 C5 N2 C7 6.7(4) . . . . ?
C6 C5 N2 C7 -175.7(2) . . . . ?
C4 C5 N2 C9 -170.6(2) . . . . ?
C6 C5 N2 C9 7.1(3) . . . . ?
N5 C9 N2 C7 -2.0(3) . . . . ?
C10 C9 N2 C7 176.95(19) . . . . ?
N5 C9 N2 C5 175.8(2) . . . . ?
C10 C9 N2 C5 -5.2(3) . . . . ?
N2 C9 N5 C8 1.3(2) . . . . ?
C10 C9 N5 C8 -177.5(2) . . . . ?
C7 C8 N5 C9 -0.2(3) . . . . ?
C11 C8 N5 C9 179.3(2) . . . . ?
C13 C14 O1 C18 0.0(4) . . . . ?
C15 C14 O1 C18 -178.8(2) . . . . ?
C16 C15 O2 C19 -108.5(3) . . . . ?
C14 C15 O2 C19 73.6(3) . . . . ?
C15 C16 O3 C20 -174.3(3) . . . . ?
C17 C16 O3 C20 7.3(4) . . . . ?

_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.841
_diffrn_reflns_theta_full        29.46
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.036
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
