# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# 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_A2-OMe
_database_code_depnum_ccdc_archive 'CCDC 1946072'
loop_
_audit_author_name
_audit_author_address
'Xiaojie Zhang'
;Tianjin University
China
;
_audit_update_record             
;
2019-08-08 deposited with the CCDC.	2019-12-03 downloaded from the CCDC.
;
_audit_creation_date             2019-06-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            A2-OMe
_chemical_name_systematic        'A2-OMe and DIB'
_chemical_formula_moiety         'C6 F4 I2, C20 H18 N4 O4'
_chemical_formula_sum            'C26 H18 F4 I2 N4 O4'
_chemical_formula_weight         780.24
_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 0.0181 0.0091 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   8.3364(3)
_cell_length_b                   8.9922(2)
_cell_length_c                   9.09840(10)
_cell_angle_alpha                82.895(2)
_cell_angle_beta                 73.539(2)
_cell_angle_gamma                84.883(2)
_cell_volume                     648.01(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    8908
_cell_measurement_temperature    160.00(10)
_cell_measurement_theta_max      76.8480
_cell_measurement_theta_min      4.9500
_shelx_estimated_absorpt_T_max   0.302
_shelx_estimated_absorpt_T_min   0.201
_exptl_absorpt_coefficient_mu    19.699
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35609
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45g (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.999
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10921
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.085
_diffrn_reflns_theta_min         4.964
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00  27.00   0.50    0.05    --  -45.87  86.00  25.00  202
  2  ω    -26.00  74.00   0.50    0.05    --   45.87 -86.00 -93.00  200
  3  ω   -173.00 -81.00   0.50    0.05    -- -100.00 -86.00 -93.00  184
  4  ω   -128.00 -27.00   0.50    0.05    -- -100.00  86.00  25.00  202
  5  ω     80.00 178.00   0.50    0.05    --  107.75  86.00  25.00  196
  6  ω     73.00 119.00   0.50    0.05    --   45.87 125.00 -30.00   92
  7  ω     73.00 119.00   0.50    0.05    --   45.87 125.00-150.00   92
  8  ω    -28.00  61.00   0.50    0.05    --   45.87 -37.00 -60.00  178
  9  ω     73.00 119.00   0.50    0.05    --   45.87 125.00 -60.00   92
 10  ω    -28.00  61.00   0.50    0.05    --   45.87 -37.00-180.00  178
 11  ω   -173.00 -27.00   0.50    0.05    -- -100.00   0.00 -90.00  292
 12  ω   -117.00 -27.00   0.50    0.05    -- -100.00 125.00 120.00  180
 13  ω   -117.00 -27.00   0.50    0.05    -- -100.00  61.00  30.00  180
 14  ω   -173.00 -84.00   0.50    0.05    -- -100.00 -94.00 -60.00  178
 15  ω   -115.00 -25.00   0.50    0.05    -- -100.00  30.00-120.00  180
 16  ω     35.00 109.00   0.50    0.05    --  107.75 -94.00-150.00  148
 17  ω     93.00 178.00   0.50    0.05    --  107.75  45.00-180.00  170
 18  ω     35.00 109.00   0.50    0.05    --  107.75 -94.00 -90.00  148
 19  ω     35.00 117.00   0.50    0.05    --  107.75-125.00 150.00  164
 20  ω     35.00 109.00   0.50    0.05    --  107.75 -94.00   0.00  148
 21  ω     35.00 109.00   0.50    0.05    --  107.75 -94.00-120.00  148
 22  ω     35.00 109.00   0.50    0.05    --  107.75 -94.00  60.00  148
 23  ω     90.00 178.00   0.50    0.05    --  107.75  15.00 -30.00  176
 24  ω     35.00 136.00   0.50    0.05    --  107.75 -86.00 -93.00  202
 25  ω     30.00 119.00   0.50    0.05    --   45.87  57.00  90.00  178
 26  ω     30.00 119.00   0.50    0.05    --   45.87  57.00  30.00  178
 27  ω     22.00 119.00   0.50    0.05    --   45.87  77.00 -60.00  194
 28  ω     22.00 119.00   0.50    0.05    --   45.87  77.00-120.00  194
 29  ω     22.00 119.00   0.50    0.05    --   45.87  77.00 120.00  194
 30  ω     22.00 119.00   0.50    0.05    --   45.87  77.00-180.00  194
 31  ω     90.00 178.00   0.50    0.05    --  107.75  15.00 120.00  176
 32  ω     92.00 135.00   0.50    0.05    --  107.75  30.00 150.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1218631000
_diffrn_orient_matrix_UB_12      0.1271649000
_diffrn_orient_matrix_UB_13      -0.0357725000
_diffrn_orient_matrix_UB_21      0.0961647000
_diffrn_orient_matrix_UB_22      -0.0861720000
_diffrn_orient_matrix_UB_23      0.1088575000
_diffrn_orient_matrix_UB_31      0.1146945000
_diffrn_orient_matrix_UB_32      -0.0794203000
_diffrn_orient_matrix_UB_33      -0.1355662000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2578
_reflns_number_total             2624
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_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_diff_density_max         0.766
_refine_diff_density_min         -1.011
_refine_diff_density_rms         0.133
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2624
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0248
_refine_ls_restrained_S_all      1.064
_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)+(0.0371P)²+1.2025P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0629
_refine_ls_wR_factor_ref         0.0637
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C6(H6), C7(H7), C9(H9), C10(H10)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
I1 I 0.59175(2) 0.82627(2) 1.15862(2) 0.01925(8) Uani 1 1 d . . . . .
F1 F 0.8224(2) 0.9837(2) 1.3218(2) 0.0273(4) Uani 1 1 d . . . . .
F2 F 0.2503(2) 0.8892(2) 1.4163(2) 0.0250(4) Uani 1 1 d . . . . .
C11 C 0.6614(4) 0.9905(3) 1.4083(3) 0.0187(6) Uani 1 1 d . . . . .
C12 C 0.5390(4) 0.9307(3) 1.3605(3) 0.0181(6) Uani 1 1 d . . . . .
C13 C 0.3765(4) 0.9417(3) 1.4562(3) 0.0185(6) Uani 1 1 d . . . . .
O1 O 1.0783(3) 0.7237(2) 0.1467(2) 0.0251(5) Uani 1 1 d . . . . .
O2 O 0.7279(3) 0.4136(3) 0.3865(2) 0.0283(5) Uani 1 1 d . . . . .
N1 N 0.8683(3) 0.6124(3) 0.4052(3) 0.0200(5) Uani 1 1 d . . . . .
H1 H 0.945124 0.671107 0.353175 0.024 Uiso 1 1 calc R . . . .
N2 N 0.6665(4) 0.7056(3) 0.8654(3) 0.0264(6) Uani 1 1 d . . . . .
C1 C 1.1135(4) 0.6022(3) -0.0832(3) 0.0190(6) Uani 1 1 d . . . . .
H1A H 1.190029 0.671647 -0.139138 0.023 Uiso 1 1 calc R . . . .
C2 C 1.1752(5) 0.8418(4) 0.0558(4) 0.0272(7) Uani 1 1 d . . . . .
H2A H 1.118697 0.891704 -0.016537 0.041 Uiso 1 1 calc GR . . . .
H2B H 1.282951 0.801139 0.001151 0.041 Uiso 1 1 calc GR . . . .
H2C H 1.189343 0.912376 0.121592 0.041 Uiso 1 1 calc GR . . . .
C3 C 1.0406(4) 0.6136(3) 0.0723(3) 0.0183(6) Uani 1 1 d . . . . .
C4 C 0.9244(4) 0.5103(3) 0.1581(3) 0.0163(5) Uani 1 1 d . . . . .
C5 C 0.8306(4) 0.5063(3) 0.3269(3) 0.0181(6) Uani 1 1 d . . . . .
C6 C 0.5989(5) 0.6063(4) 0.8057(4) 0.0311(8) Uani 1 1 d . . . . .
H6 H 0.505198 0.559787 0.869785 0.037 Uiso 1 1 calc R . . . .
C7 C 0.6568(4) 0.5672(4) 0.6565(4) 0.0269(7) Uani 1 1 d . . . . .
H7 H 0.604429 0.496913 0.622023 0.032 Uiso 1 1 calc R . . . .
C8 C 0.7969(4) 0.6374(3) 0.5599(3) 0.0180(6) Uani 1 1 d . . . . .
C9 C 0.8695(4) 0.7409(3) 0.6191(3) 0.0200(6) Uani 1 1 d . . . . .
H9 H 0.963002 0.789679 0.557802 0.024 Uiso 1 1 calc R . . . .
C10 C 0.8005(4) 0.7702(4) 0.7704(4) 0.0236(6) Uani 1 1 d . . . . .
H10 H 0.850839 0.839472 0.808458 0.028 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
I1 C12 2.084(3) . ?
F1 C11 1.350(3) . ?
F2 C13 1.344(3) . ?
C11 C12 1.388(4) . ?
C11 C13 1.387(4) 2_678 ?
C12 C13 1.390(4) . ?
O1 C2 1.422(4) . ?
O1 C3 1.370(4) . ?
O2 C5 1.214(4) . ?
N1 H1 0.8600 . ?
N1 C5 1.365(4) . ?
N1 C8 1.403(4) . ?
N2 C6 1.339(5) . ?
N2 C10 1.333(4) . ?
C1 H1A 0.9300 . ?
C1 C3 1.385(4) . ?
C1 C4 1.391(4) 2_765 ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C4 1.402(4) . ?
C4 C5 1.511(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.384(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.396(4) . ?
C8 C9 1.390(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.382(4) . ?
C10 H10 0.9300 . ?

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
F1 C11 C12 119.9(3) . . ?
F1 C11 C13 118.2(3) . 2_678 ?
C13 C11 C12 121.8(3) 2_678 . ?
C11 C12 I1 122.8(2) . . ?
C11 C12 C13 116.4(3) . . ?
C13 C12 I1 120.7(2) . . ?
F2 C13 C11 118.2(3) . 2_678 ?
F2 C13 C12 120.0(3) . . ?
C11 C13 C12 121.8(3) 2_678 . ?
C3 O1 C2 118.0(2) . . ?
C5 N1 H1 116.0 . . ?
C5 N1 C8 127.9(3) . . ?
C8 N1 H1 116.0 . . ?
C10 N2 C6 115.8(3) . . ?
C3 C1 H1A 119.0 . . ?
C3 C1 C4 121.9(3) . 2_765 ?
C4 C1 H1A 119.0 2_765 . ?
O1 C2 H2A 109.5 . . ?
O1 C2 H2B 109.5 . . ?
O1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O1 C3 C1 122.1(3) . . ?
O1 C3 C4 118.2(3) . . ?
C1 C3 C4 119.7(3) . . ?
C1 C4 C3 118.3(3) 2_765 . ?
C1 C4 C5 114.4(3) 2_765 . ?
C3 C4 C5 127.3(3) . . ?
O2 C5 N1 123.3(3) . . ?
O2 C5 C4 120.8(3) . . ?
N1 C5 C4 116.0(3) . . ?
N2 C6 H6 117.3 . . ?
N2 C6 C7 125.4(3) . . ?
C7 C6 H6 117.3 . . ?
C6 C7 H7 121.3 . . ?
C6 C7 C8 117.4(3) . . ?
C8 C7 H7 121.3 . . ?
C7 C8 N1 124.2(3) . . ?
C9 C8 N1 117.4(3) . . ?
C9 C8 C7 118.3(3) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 C8 119.0(3) . . ?
C10 C9 H9 120.5 . . ?
N2 C10 C9 124.1(3) . . ?
N2 C10 H10 117.9 . . ?
C9 C10 H10 117.9 . . ?

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
I1 C12 C13 F2 -2.3(4) . . . . ?
I1 C12 C13 C11 179.4(2) . . . 2_678 ?
F1 C11 C12 I1 0.6(4) . . . . ?
F1 C11 C12 C13 179.8(3) . . . . ?
C11 C12 C13 F2 178.6(3) . . . . ?
C11 C12 C13 C11 0.3(5) . . . 2_678 ?
C13 C11 C12 I1 -179.4(2) 2_678 . . . ?
C13 C11 C12 C13 -0.3(5) 2_678 . . . ?
O1 C3 C4 C1 -179.6(3) . . . 2_765 ?
O1 C3 C4 C5 1.0(5) . . . . ?
N1 C8 C9 C10 178.9(3) . . . . ?
N2 C6 C7 C8 -0.3(6) . . . . ?
C1 C3 C4 C1 0.3(5) . . . 2_765 ?
C1 C3 C4 C5 -179.0(3) . . . . ?
C1 C4 C5 O2 -2.2(4) 2_765 . . . ?
C1 C4 C5 N1 178.2(3) 2_765 . . . ?
C2 O1 C3 C1 9.7(4) . . . . ?
C2 O1 C3 C4 -170.3(3) . . . . ?
C3 C4 C5 O2 177.2(3) . . . . ?
C3 C4 C5 N1 -2.4(4) . . . . ?
C4 C1 C3 O1 179.6(3) 2_765 . . . ?
C4 C1 C3 C4 -0.3(5) 2_765 . . . ?
C5 N1 C8 C7 -8.7(5) . . . . ?
C5 N1 C8 C9 172.6(3) . . . . ?
C6 N2 C10 C9 0.3(5) . . . . ?
C6 C7 C8 N1 -178.5(3) . . . . ?
C6 C7 C8 C9 0.2(5) . . . . ?
C7 C8 C9 C10 0.0(5) . . . . ?
C8 N1 C5 O2 -1.9(5) . . . . ?
C8 N1 C5 C4 177.7(3) . . . . ?
C8 C9 C10 N2 -0.3(5) . . . . ?
C10 N2 C6 C7 0.0(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.667
_oxdiff_exptl_absorpt_empirical_full_min 0.628
_exptl_crystal_recrystallization_method 'Vapour deposition'
_chemical_compound_source        chemical
