# 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_6045
_database_code_depnum_ccdc_archive 'CCDC 1453940'
_audit_update_record             
;
2016-02-16 deposited with the CCDC.
2016-03-24 downloaded from the CCDC.
;
_audit_creation_date             2016-02-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_systematic        
'Dimethyl 5,8-dimethylquinoxaline-2,3-dicarboxylate '
_chemical_formula_moiety         'C14 H14 N2 O4'
_chemical_formula_sum            'C14 H14 N2 O4'
_chemical_formula_weight         274.28
_chemical_oxdiff_formula         'C14 H16 N2 O4'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   8.2596(12)
_cell_length_b                   8.9504(13)
_cell_length_c                   10.0044(15)
_cell_angle_alpha                75.628(13)
_cell_angle_beta                 72.518(13)
_cell_angle_gamma                85.932(12)
_cell_volume                     683.35(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1349
_cell_measurement_temperature    140
_cell_measurement_theta_max      71.9038
_cell_measurement_theta_min      4.7680
_exptl_absorpt_coefficient_mu    0.828
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dull whiteish white'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.3329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             289.0376
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane '
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5187
_diffrn_reflns_theta_full        72.0498
_diffrn_reflns_theta_max         72.05
_diffrn_reflns_theta_min         4.77
_diffrn_ambient_temperature      140
_diffrn_detector_area_resol_mean 16.1293
_diffrn_measured_fraction_theta_full 0.9605
_diffrn_measured_fraction_theta_max 0.9566
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -60.00  -29.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   57.0000 -120.0000 31

#__ type_ start__ end____ width___ exp.time_
  2 omega  -44.00   23.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   38.0000  -30.0000 67

#__ type_ start__ end____ width___ exp.time_
  3 omega  -49.00   30.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   38.0000 -150.0000 79

#__ type_ start__ end____ width___ exp.time_
  4 omega -110.00  -36.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  178.0000  -90.0000 74

#__ type_ start__ end____ width___ exp.time_
  5 omega  -50.00   29.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   25.0000  120.0000 79

#__ type_ start__ end____ width___ exp.time_
  6 omega  -27.00   23.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   57.0000 -120.0000 50

#__ type_ start__ end____ width___ exp.time_
  7 omega -110.00  -54.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  178.0000    0.0000 56

#__ type_ start__ end____ width___ exp.time_
  8 omega   47.00  105.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       55.4518 -125.0000  -30.0000 58

#__ type_ start__ end____ width___ exp.time_
  9 omega   77.00  123.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       55.4518   77.0000   90.0000 46

#__ type_ start__ end____ width___ exp.time_
 10 omega   42.00   88.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.9036  -25.0000   30.0000 46

#__ type_ start__ end____ width___ exp.time_
 11 omega   53.00   89.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.9036  -38.0000  120.0000 36

#__ type_ start__ end____ width___ exp.time_
 12 omega   56.00  133.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.9036  -63.0000 -180.0000 77

#__ type_ start__ end____ width___ exp.time_
 13 omega   39.00   89.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.9036  -38.0000  -30.0000 50

#__ type_ start__ end____ width___ exp.time_
 14 omega   61.00  113.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.9036 -111.0000  -30.0000 52

#__ type_ start__ end____ width___ exp.time_
 15 omega   49.00  110.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.9036 -111.0000 -150.0000 61

#__ type_ start__ end____ width___ exp.time_
 16 omega   38.00   83.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.9036  -38.0000   90.0000 45

#__ type_ start__ end____ width___ exp.time_
 17 omega   39.00   81.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.9036  -42.0000  176.0000 42

#__ type_ start__ end____ width___ exp.time_
 18 omega   47.00  104.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.9036  -50.0000  -90.0000 57

#__ type_ start__ end____ width___ exp.time_
 19 omega   42.00   83.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.9036  -50.0000   30.0000 41

#__ type_ start__ end____ width___ exp.time_
 20 omega  100.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.9036    0.0000   60.0000 78

#__ type_ start__ end____ width___ exp.time_
 21 omega   43.00  156.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.9036   12.0000    0.0000 113

#__ type_ start__ end____ width___ exp.time_
 22 omega   46.00  138.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.9036  -91.0000   30.0000 92

#__ type_ start__ end____ width___ exp.time_
 23 omega -113.00  -12.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000  -30.0000 101

#__ type_ start__ end____ width___ exp.time_
 24 omega -111.00  -21.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -57.0000   60.0000 90

#__ type_ start__ end____ width___ exp.time_
 25 omega -111.00  -21.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -57.0000 -120.0000 90

#__ type_ start__ end____ width___ exp.time_
 26 omega -113.00  -12.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000  150.0000 101

#__ type_ start__ end____ width___ exp.time_
 27 omega -110.00  -20.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -63.0000   30.0000 90

#__ type_ start__ end____ width___ exp.time_
 28 omega -111.00  -21.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -57.0000 -180.0000 90
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1759980000
_diffrn_orient_matrix_UB_12      -0.0176198000
_diffrn_orient_matrix_UB_13      0.0254941000
_diffrn_orient_matrix_UB_21      0.0445385000
_diffrn_orient_matrix_UB_22      -0.1273872000
_diffrn_orient_matrix_UB_23      -0.0840683000
_diffrn_orient_matrix_UB_31      0.0726736000
_diffrn_orient_matrix_UB_32      0.1226123000
_diffrn_orient_matrix_UB_33      -0.1411345000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -9
_reflns_limit_k_max              10
_reflns_limit_k_min              -10
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                1550
_reflns_number_total             2577
_reflns_odcompleteness_completeness 99.22
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.2662
_refine_diff_density_min         -0.2771
_refine_diff_density_rms         0.0641
_refine_ls_d_res_high            0.8104
_refine_ls_d_res_low             9.2670
_refine_ls_goodness_of_fit_ref   1.1126
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2577
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0977
_refine_ls_R_factor_gt           0.0630
_refine_ls_restrained_S_all      1.1126
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1127P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1780
_refine_ls_wR_factor_ref         0.2209
_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:
 C11(H11), C10(H10)
2.b Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c), C13(H13a,H13b,H13c), C1(H1a,H1b,H1c), C6(H6a,H6b,H6c)
;
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_refinement_flags_posn
C3 C 0.4449(3) 0.0182(3) 0.2791(3) 0.0576(7) Uani 1.000000 .
N2 N 0.6167(3) -0.1918(3) 0.2105(2) 0.0611(6) Uani 1.000000 .
N1 N 0.5237(3) 0.1197(2) 0.1617(2) 0.0585(6) Uani 1.000000 .
C8 C 0.6538(3) 0.0680(3) 0.0623(3) 0.0561(7) Uani 1.000000 .
C7 C 0.7004(3) -0.0893(3) 0.0861(3) 0.0564(7) Uani 1.000000 .
C12 C 0.8327(3) -0.1430(3) -0.0191(3) 0.0628(7) Uani 1.000000 .
C9 C 0.7388(3) 0.1763(3) -0.0654(3) 0.0621(7) Uani 1.000000 .
O1 O 0.2564(2) 0.2160(2) 0.3392(2) 0.0728(6) Uani 1.000000 .
C4 C 0.4927(3) -0.1381(3) 0.3037(3) 0.0585(7) Uani 1.000000 .
O2 O 0.2365(3) -0.0047(3) 0.5065(2) 0.0973(8) Uani 1.000000 .
O4 O 0.4695(3) -0.2778(2) 0.5395(2) 0.0783(6) Uani 1.000000 .
C11 C 0.9133(4) -0.0362(4) -0.1398(3) 0.0688(8) Uani 1.000000 .
H11 H 1.0033(4) -0.0686(4) -0.2114(3) 0.0825(9) Uiso 1.000000 R
C2 C 0.3015(4) 0.0737(4) 0.3873(3) 0.0668(8) Uani 1.000000 .
C10 C 0.8680(4) 0.1202(4) -0.1624(3) 0.0704(8) Uani 1.000000 .
H10 H 0.9294(4) 0.1900(4) -0.2484(3) 0.0845(10) Uiso 1.000000 R
O3 O 0.2810(3) -0.3306(3) 0.4372(2) 0.0840(7) Uani 1.000000 .
C5 C 0.3991(4) -0.2577(3) 0.4334(3) 0.0655(7) Uani 1.000000 .
C14 C 0.6880(4) 0.3424(4) -0.0901(3) 0.0785(9) Uani 1.000000 .
H14a H 0.5665(7) 0.3503(4) -0.081(2) 0.1177(13) Uiso 1.000000 GR
H14b H 0.711(3) 0.3878(7) -0.0181(15) 0.1177(13) Uiso 1.000000 GR
H14c H 0.753(2) 0.3978(6) -0.1870(9) 0.1177(13) Uiso 1.000000 GR
C13 C 0.8778(4) -0.3105(4) 0.0030(4) 0.0861(10) Uani 1.000000 .
H13a H 0.889(3) -0.3495(7) 0.1002(10) 0.1291(15) Uiso 1.000000 GR
H13b H 0.7881(15) -0.3681(5) -0.008(3) 0.1291(15) Uiso 1.000000 GR
H13c H 0.9854(16) -0.3236(5) -0.0686(17) 0.1291(15) Uiso 1.000000 GR
C1 C 0.1215(5) 0.2797(4) 0.4405(4) 0.1039(12) Uani 1.000000 .
H1a H 0.089(2) 0.3807(15) 0.3911(8) 0.1558(19) Uiso 1.000000 GR
H1b H 0.0232(13) 0.2100(16) 0.479(2) 0.1558(19) Uiso 1.000000 GR
H1c H 0.1617(12) 0.291(3) 0.5202(16) 0.1558(19) Uiso 1.000000 GR
C6 C 0.3851(5) -0.3876(4) 0.6716(3) 0.0911(11) Uani 1.000000 .
H6a H 0.369(3) -0.4852(10) 0.6495(5) 0.1366(16) Uiso 1.000000 GR
H6b H 0.4549(15) -0.405(2) 0.7378(11) 0.1366(16) Uiso 1.000000 GR
H6c H 0.2745(14) -0.3467(13) 0.7169(14) 0.1366(16) Uiso 1.000000 GR


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
C3 N1 1.313(3) . ?
C3 C4 1.408(4) . ?
C3 C2 1.494(4) . ?
N2 C7 1.369(3) . ?
N2 C4 1.315(3) . ?
N1 C8 1.369(3) . ?
C8 C7 1.413(4) . ?
C8 C9 1.417(4) . ?
C7 C12 1.420(3) . ?
C12 C11 1.360(4) . ?
C12 C13 1.497(4) . ?
C9 C10 1.370(4) . ?
C9 C14 1.496(4) . ?
O1 C2 1.315(3) . ?
O1 C1 1.453(3) . ?
C4 C5 1.501(4) . ?
O2 C2 1.207(3) . ?
O4 C5 1.326(3) . ?
O4 C6 1.448(3) . ?
C11 C10 1.403(4) . ?
O3 C5 1.198(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
C4 C3 N1 121.6(2) . . ?
C2 C3 N1 117.8(3) . . ?
C2 C3 C4 120.5(2) . . ?
C4 N2 C7 117.5(2) . . ?
C8 N1 C3 117.6(2) . . ?
C7 C8 N1 120.8(2) . . ?
C9 C8 N1 118.0(3) . . ?
C9 C8 C7 121.2(2) . . ?
C8 C7 N2 120.1(2) . . ?
C12 C7 N2 119.4(3) . . ?
C12 C7 C8 120.5(2) . . ?
C11 C12 C7 117.0(3) . . ?
C13 C12 C7 120.7(3) . . ?
C13 C12 C11 122.3(3) . . ?
C10 C9 C8 116.4(3) . . ?
C14 C9 C8 120.8(3) . . ?
C14 C9 C10 122.8(3) . . ?
C1 O1 C2 116.0(2) . . ?
N2 C4 C3 122.4(2) . . ?
C5 C4 C3 122.6(2) . . ?
C5 C4 N2 114.9(2) . . ?
C6 O4 C5 115.7(2) . . ?
C10 C11 C12 122.3(3) . . ?
O1 C2 C3 112.9(2) . . ?
O2 C2 C3 122.8(3) . . ?
O2 C2 O1 124.2(3) . . ?
C11 C10 C9 122.6(3) . . ?
O4 C5 C4 111.4(2) . . ?
O3 C5 C4 123.9(3) . . ?
O3 C5 O4 124.6(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_name_common            'dimethyl quinoxaline  dicarboxylate '
_chemical_melting_point          403.15
