# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_dm-aj-l4-50_mo
_database_code_depnum_ccdc_archive 'CCDC 1996667'
loop_
_audit_author_name
_audit_author_address
'Jyoti Prasad Biswas'
;IIT Bombay
India
;
_audit_update_record             
;
2020-04-13 deposited with the CCDC.	2020-05-07 downloaded from the CCDC.
;
_audit_creation_date             2020-04-13
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.8(C12 H9 F N2 O3)'
_chemical_formula_sum            'C9.60 H7.20 F0.80 N1.60 O2.40'
_chemical_formula_weight         198.57
_chemical_absolute_configuration unk
_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'
F F 0.0171 0.0103 '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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
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'

_cell_length_a                   13.7895(17)
_cell_length_b                   20.620(2)
_cell_length_c                   3.8818(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1103.8(3)
_cell_formula_units_Z            5
_cell_measurement_reflns_used    1495
_cell_measurement_temperature    150
_cell_measurement_theta_max      28.1340
_cell_measurement_theta_min      2.4520
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       trapezoid
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1011
_diffrn_reflns_av_unetI/netI     0.1333
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            6191
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        24.991
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_min         2.467
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -63.00  70.00   1.00    8.00    --  -20.00   0.00-180.00  133
  2  ω    -96.00  19.00   1.00    8.00    --  -20.00 -72.00  36.00  115
  3  ω    -72.00 -42.00   1.00    8.00    --  -20.00 -72.00-180.00   30
  4  ω   -110.00 -80.00   1.00    8.00    --  -20.00   0.00 108.00   30
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0047214000
_diffrn_orient_matrix_UB_12      -0.0073641000
_diffrn_orient_matrix_UB_13      0.1777968000
_diffrn_orient_matrix_UB_21      0.0471998000
_diffrn_orient_matrix_UB_22      0.0136476000
_diffrn_orient_matrix_UB_23      0.0002543000
_diffrn_orient_matrix_UB_31      -0.0198518000
_diffrn_orient_matrix_UB_32      0.0306910000
_diffrn_orient_matrix_UB_33      0.0426587000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.686
_reflns_Friedel_fraction_full    0.949
_reflns_Friedel_fraction_max     0.949
_reflns_number_gt                1140
_reflns_number_total             1909
_reflns_odcompleteness_completeness 93.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.08
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details 
;
 Flack x determined using 250 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.7(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1909
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1315
_refine_ls_R_factor_gt           0.0710
_refine_ls_restrained_S_all      1.069
_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)+(0.0424P)²+0.3265P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1277
_refine_ls_wR_factor_ref         0.1654
_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:
 C007(H007), C008(H008), C009(H009), C00A(H00A), C00E(H00E), C00I(H00I)
2.b Idealised Me refined as rotating group:
 C00C(H00B,H00C,H00D)
;
_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
F001 F 0.5629(3) 0.14326(17) 0.4459(14) 0.0482(14) Uani 1 1 d . . . . .
O002 O 0.4805(3) 0.4024(2) 0.5820(14) 0.0351(15) Uani 1 1 d . . . . .
O003 O 0.4106(4) 0.1418(2) 0.0271(17) 0.0491(16) Uani 1 1 d . . . . .
O004 O 0.2948(4) 0.2027(3) 0.216(2) 0.060(2) Uani 1 1 d . . . . .
N005 N 0.3273(4) 0.3875(2) 0.8245(18) 0.0307(16) Uani 1 1 d . . . . .
N006 N 0.3807(5) 0.1885(3) 0.195(2) 0.0410(17) Uani 1 1 d . . . . .
C007 C 0.5847(4) 0.3134(3) 0.658(2) 0.033(2) Uani 1 1 d . . . . .
H007 H 0.6311 0.3423 0.7547 0.040 Uiso 1 1 calc R U . . .
C008 C 0.2421(5) 0.4142(3) 0.922(2) 0.0298(19) Uani 1 1 d . . . . .
H008 H 0.1954 0.3868 1.0275 0.036 Uiso 1 1 calc R U . . .
C009 C 0.6064(5) 0.2483(4) 0.621(2) 0.036(2) Uani 1 1 d . . . . .
H009 H 0.6671 0.2320 0.6983 0.044 Uiso 1 1 calc R U . . .
C00A C 0.2883(5) 0.5178(3) 0.726(2) 0.0338(19) Uani 1 1 d . . . . .
H00A H 0.2757 0.5627 0.6932 0.041 Uiso 1 1 calc R U . . .
C00B C 0.2186(5) 0.4786(3) 0.878(2) 0.0302(18) Uani 1 1 d . . . . .
C00C C 0.1212(4) 0.5034(3) 0.997(3) 0.041(2) Uani 1 1 d . . . . .
H00B H 0.0877 0.5243 0.8041 0.062 Uiso 1 1 calc R U . . .
H00C H 0.1305 0.5349 1.1831 0.062 Uiso 1 1 calc R U . . .
H00D H 0.0821 0.4670 1.0817 0.062 Uiso 1 1 calc R U . . .
C00D C 0.5407(5) 0.2076(3) 0.474(2) 0.0327(19) Uani 1 1 d . . . . .
C00E C 0.3758(5) 0.4921(3) 0.624(2) 0.0303(19) Uani 1 1 d . . . . .
H00E H 0.4244 0.5184 0.5217 0.036 Uiso 1 1 calc R U . . .
C00F C 0.4950(5) 0.3361(3) 0.555(2) 0.0284(18) Uani 1 1 d . . . . .
C00G C 0.3904(4) 0.4265(3) 0.677(2) 0.0282(17) Uani 1 1 d . . . . .
C00H C 0.4521(4) 0.2306(3) 0.364(2) 0.0281(17) Uani 1 1 d . . . . .
C00I C 0.4284(4) 0.2952(3) 0.404(2) 0.0287(19) Uani 1 1 d . . . . .
H00I H 0.3673 0.3111 0.3285 0.034 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F001 C00D 1.366(7) . ?
O002 C00F 1.386(7) . ?
O002 C00G 1.388(7) . ?
O003 N006 1.235(8) . ?
O004 N006 1.223(6) . ?
N005 C008 1.351(8) . ?
N005 C00G 1.316(8) . ?
N006 C00H 1.467(9) . ?
C007 H007 0.9500 . ?
C007 C009 1.383(9) . ?
C007 C00F 1.383(8) . ?
C008 H008 0.9500 . ?
C008 C00B 1.378(8) . ?
C009 H009 0.9500 . ?
C009 C00D 1.362(10) . ?
C00A H00A 0.9500 . ?
C00A C00B 1.387(9) . ?
C00A C00E 1.377(8) . ?
C00B C00C 1.510(8) . ?
C00C H00B 0.9800 . ?
C00C H00C 0.9800 . ?
C00C H00D 0.9800 . ?
C00D C00H 1.378(8) . ?
C00E H00E 0.9500 . ?
C00E C00G 1.382(8) . ?
C00F C00I 1.378(9) . ?
C00H C00I 1.379(8) . ?
C00I H00I 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
C00F O002 C00G 120.2(5) . . ?
C00G N005 C008 116.5(5) . . ?
O003 N006 C00H 118.3(6) . . ?
O004 N006 O003 123.0(7) . . ?
O004 N006 C00H 118.7(7) . . ?
C009 C007 H007 120.3 . . ?
C00F C007 H007 120.3 . . ?
C00F C007 C009 119.5(6) . . ?
N005 C008 H008 117.8 . . ?
N005 C008 C00B 124.3(6) . . ?
C00B C008 H008 117.8 . . ?
C007 C009 H009 120.1 . . ?
C00D C009 C007 119.9(6) . . ?
C00D C009 H009 120.1 . . ?
C00B C00A H00A 119.8 . . ?
C00E C00A H00A 119.8 . . ?
C00E C00A C00B 120.3(6) . . ?
C008 C00B C00A 116.8(6) . . ?
C008 C00B C00C 119.8(6) . . ?
C00A C00B C00C 123.4(6) . . ?
C00B C00C H00B 109.5 . . ?
C00B C00C H00C 109.5 . . ?
C00B C00C H00D 109.5 . . ?
H00B C00C H00C 109.5 . . ?
H00B C00C H00D 109.5 . . ?
H00C C00C H00D 109.5 . . ?
F001 C00D C00H 120.6(6) . . ?
C009 C00D F001 118.9(6) . . ?
C009 C00D C00H 120.5(6) . . ?
C00A C00E H00E 121.2 . . ?
C00A C00E C00G 117.6(6) . . ?
C00G C00E H00E 121.2 . . ?
C007 C00F O002 116.2(6) . . ?
C00I C00F O002 122.8(6) . . ?
C00I C00F C007 120.8(6) . . ?
N005 C00G O002 119.3(6) . . ?
N005 C00G C00E 124.5(6) . . ?
C00E C00G O002 116.1(6) . . ?
C00D C00H N006 121.9(6) . . ?
C00D C00H C00I 120.5(6) . . ?
C00I C00H N006 117.5(6) . . ?
C00F C00I C00H 118.8(6) . . ?
C00F C00I H00I 120.6 . . ?
C00H C00I H00I 120.6 . . ?

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
F001 C00D C00H N006 -3.8(12) . . . . ?
F001 C00D C00H C00I 177.6(7) . . . . ?
O002 C00F C00I C00H 175.1(7) . . . . ?
O003 N006 C00H C00D -29.2(11) . . . . ?
O003 N006 C00H C00I 149.4(7) . . . . ?
O004 N006 C00H C00D 153.6(8) . . . . ?
O004 N006 C00H C00I -27.8(12) . . . . ?
N005 C008 C00B C00A -0.7(12) . . . . ?
N005 C008 C00B C00C -179.9(8) . . . . ?
N006 C00H C00I C00F -178.6(7) . . . . ?
C007 C009 C00D F001 -178.6(7) . . . . ?
C007 C009 C00D C00H -0.7(13) . . . . ?
C007 C00F C00I C00H 1.3(12) . . . . ?
C008 N005 C00G O002 177.8(6) . . . . ?
C008 N005 C00G C00E 1.6(12) . . . . ?
C009 C007 C00F O002 -176.5(7) . . . . ?
C009 C007 C00F C00I -2.3(12) . . . . ?
C009 C00D C00H N006 178.3(8) . . . . ?
C009 C00D C00H C00I -0.3(12) . . . . ?
C00A C00E C00G O002 -177.9(7) . . . . ?
C00A C00E C00G N005 -1.6(12) . . . . ?
C00B C00A C00E C00G 0.4(12) . . . . ?
C00D C00H C00I C00F 0.0(12) . . . . ?
C00E C00A C00B C008 0.7(12) . . . . ?
C00E C00A C00B C00C 179.8(8) . . . . ?
C00F O002 C00G N005 17.4(11) . . . . ?
C00F O002 C00G C00E -166.1(7) . . . . ?
C00F C007 C009 C00D 2.0(13) . . . . ?
C00G O002 C00F C007 -143.4(7) . . . . ?
C00G O002 C00F C00I 42.4(11) . . . . ?
C00G N005 C008 C00B -0.4(12) . . . . ?

_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 1.656
_oxdiff_exptl_absorpt_empirical_full_min 0.659
####################################################################### 
# 
# 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_dm-ta-53_mo
_database_code_depnum_ccdc_archive 'CCDC 1996668'
loop_
_audit_author_name
_audit_author_address
'Jyoti Prasad Biswas'
;IIT Bombay
India
;
_audit_update_record             
;
2020-04-13 deposited with the CCDC.	2020-05-07 downloaded from the CCDC.
;
_audit_creation_date             2020-04-13
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.444(C12 H10 N2 O4)'
_chemical_formula_sum            'C5.33 H4.44 N0.89 O1.78'
_chemical_formula_weight         109.43
_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.5310(4)
_cell_length_b                   11.1285(5)
_cell_length_c                   12.0481(6)
_cell_angle_alpha                90
_cell_angle_beta                 110.333(5)
_cell_angle_gamma                90
_cell_volume                     1072.55(9)
_cell_formula_units_Z            9
_cell_measurement_reflns_used    4162
_cell_measurement_temperature    150
_cell_measurement_theta_max      31.0820
_cell_measurement_theta_min      3.5960
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41573
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       trapezoid
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.076
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.950
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5567
_diffrn_reflns_point_group_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         3.146
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.950
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -72.00  53.50   0.50    8.00    --  -20.00   0.00-108.00  251
  2  ω    -13.50  18.00   0.50    8.00    --  -20.00 -72.00 108.00   63
  3  ω    -73.00 -43.00   0.50    8.00    --  -20.00 -72.00  36.00   60
  4  ω   -107.00  -3.50   0.50    8.00    --  -20.00   0.00 -36.00  207
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0700860000
_diffrn_orient_matrix_UB_12      -0.0317796000
_diffrn_orient_matrix_UB_13      0.0381990000
_diffrn_orient_matrix_UB_21      0.0321351000
_diffrn_orient_matrix_UB_22      0.0541235000
_diffrn_orient_matrix_UB_23      0.0305490000
_diffrn_orient_matrix_UB_31      -0.0437565000
_diffrn_orient_matrix_UB_32      -0.0111068000
_diffrn_orient_matrix_UB_33      0.0393876000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1633
_reflns_number_total             1797
_reflns_odcompleteness_completeness 79.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.06
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1797
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0414
_refine_ls_restrained_S_all      1.065
_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)+(0.0704P)²+0.3562P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1143
_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:
 C008(H008), C009(H009), C00A(H00D), C00B(H00E), C00C(H00F), C00H(H00H),
 C00I(H00I)
2.b Idealised Me refined as rotating group:
 C007(H00A,H00B,H00C)
;
_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
O001 O 0.39602(13) 0.38502(10) 0.28280(9) 0.0163(3) Uani 1 1 d . . . . .
O002 O 0.27780(13) 0.42737(10) 0.70626(9) 0.0176(3) Uani 1 1 d . . . . .
O003 O 0.56298(13) 0.13241(10) 0.52863(10) 0.0208(3) Uani 1 1 d . . . . .
O004 O 0.64041(13) 0.24350(10) 0.40924(10) 0.0197(3) Uani 1 1 d . . . . .
N005 N 0.06404(15) 0.28644(12) 0.64695(11) 0.0158(3) Uani 1 1 d . . . . .
N006 N 0.55422(15) 0.22513(12) 0.47047(11) 0.0142(3) Uani 1 1 d . . . . .
C007 C 0.31987(19) 0.46910(15) 0.18864(13) 0.0182(4) Uani 1 1 d . . . . .
H00A H 0.3625 0.4552 0.1240 0.027 Uiso 1 1 calc R U . . .
H00B H 0.3470 0.5513 0.2184 0.027 Uiso 1 1 calc R U . . .
H00C H 0.1983 0.4581 0.1595 0.027 Uiso 1 1 calc R U . . .
C008 C 0.40523(17) 0.32424(14) 0.58432(13) 0.0139(4) Uani 1 1 d . . . . .
H008 H 0.4566 0.2693 0.6467 0.017 Uiso 1 1 calc R U . . .
C009 C 0.21985(18) 0.49002(14) 0.50487(13) 0.0153(4) Uani 1 1 d . . . . .
H009 H 0.1452 0.5492 0.5144 0.018 Uiso 1 1 calc R U . . .
C00A C -0.05175(18) 0.22238(15) 0.67461(14) 0.0178(4) Uani 1 1 d . . . . .
H00D H -0.1199 0.1680 0.6172 0.021 Uiso 1 1 calc R U . . .
C00B C 0.25026(17) 0.48258(14) 0.39921(13) 0.0146(4) Uani 1 1 d . . . . .
H00E H 0.1950 0.5363 0.3365 0.018 Uiso 1 1 calc R U . . .
C00C C 0.02385(19) 0.31111(15) 0.86568(14) 0.0210(4) Uani 1 1 d . . . . .
H00F H 0.0105 0.3192 0.9404 0.025 Uiso 1 1 calc R U . . .
C00D C 0.15694(17) 0.36081(14) 0.72877(13) 0.0141(4) Uani 1 1 d . . . . .
C00E C 0.36096(17) 0.39724(14) 0.38379(13) 0.0128(4) Uani 1 1 d . . . . .
C00F C 0.43678(17) 0.31821(14) 0.47850(13) 0.0134(4) Uani 1 1 d . . . . .
C00G C 0.29803(18) 0.41149(14) 0.59654(13) 0.0149(4) Uani 1 1 d . . . . .
C00H C 0.14259(19) 0.37795(15) 0.83970(13) 0.0179(4) Uani 1 1 d . . . . .
H00H H 0.2120 0.4335 0.8950 0.021 Uiso 1 1 calc R U . . .
C00I C -0.07669(19) 0.23137(15) 0.78125(15) 0.0210(4) Uani 1 1 d . . . . .
H00I H -0.1599 0.1847 0.7970 0.025 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C007 1.4395(18) . ?
O001 C00E 1.3569(18) . ?
O002 C00D 1.3710(19) . ?
O002 C00G 1.4025(19) . ?
O003 N006 1.2349(17) . ?
O004 N006 1.2261(17) . ?
N005 C00A 1.351(2) . ?
N005 C00D 1.320(2) . ?
N006 C00F 1.467(2) . ?
C007 H00A 0.9800 . ?
C007 H00B 0.9800 . ?
C007 H00C 0.9800 . ?
C008 H008 0.9500 . ?
C008 C00F 1.393(2) . ?
C008 C00G 1.376(2) . ?
C009 H009 0.9500 . ?
C009 C00B 1.387(2) . ?
C009 C00G 1.384(2) . ?
C00A H00D 0.9500 . ?
C00A C00I 1.377(2) . ?
C00B H00E 0.9500 . ?
C00B C00E 1.397(2) . ?
C00C H00F 0.9500 . ?
C00C C00H 1.377(2) . ?
C00C C00I 1.397(2) . ?
C00D C00H 1.397(2) . ?
C00E C00F 1.407(2) . ?
C00H H00H 0.9500 . ?
C00I H00I 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
C00E O001 C007 117.50(12) . . ?
C00D O002 C00G 117.76(12) . . ?
C00D N005 C00A 116.59(13) . . ?
O003 N006 C00F 117.41(12) . . ?
O004 N006 O003 123.37(13) . . ?
O004 N006 C00F 119.20(12) . . ?
O001 C007 H00A 109.5 . . ?
O001 C007 H00B 109.5 . . ?
O001 C007 H00C 109.5 . . ?
H00A C007 H00B 109.5 . . ?
H00A C007 H00C 109.5 . . ?
H00B C007 H00C 109.5 . . ?
C00F C008 H008 120.7 . . ?
C00G C008 H008 120.7 . . ?
C00G C008 C00F 118.60(14) . . ?
C00B C009 H009 119.9 . . ?
C00G C009 H009 119.9 . . ?
C00G C009 C00B 120.17(14) . . ?
N005 C00A H00D 118.1 . . ?
N005 C00A C00I 123.73(15) . . ?
C00I C00A H00D 118.1 . . ?
C009 C00B H00E 119.6 . . ?
C009 C00B C00E 120.89(14) . . ?
C00E C00B H00E 119.6 . . ?
C00H C00C H00F 120.3 . . ?
C00H C00C C00I 119.44(15) . . ?
C00I C00C H00F 120.3 . . ?
O002 C00D C00H 115.95(14) . . ?
N005 C00D O002 119.26(13) . . ?
N005 C00D C00H 124.80(14) . . ?
O001 C00E C00B 123.88(13) . . ?
O001 C00E C00F 118.82(13) . . ?
C00B C00E C00F 117.29(14) . . ?
C008 C00F N006 116.60(13) . . ?
C008 C00F C00E 122.10(14) . . ?
C00E C00F N006 121.30(13) . . ?
C008 C00G O002 119.58(14) . . ?
C008 C00G C009 120.92(14) . . ?
C009 C00G O002 119.31(14) . . ?
C00C C00H C00D 117.36(15) . . ?
C00C C00H H00H 121.3 . . ?
C00D C00H H00H 121.3 . . ?
C00A C00I C00C 118.08(15) . . ?
C00A C00I H00I 121.0 . . ?
C00C C00I H00I 121.0 . . ?

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
O001 C00E C00F N006 1.1(2) . . . . ?
O001 C00E C00F C008 -179.16(12) . . . . ?
O002 C00D C00H C00C -179.11(13) . . . . ?
O003 N006 C00F C008 29.26(17) . . . . ?
O003 N006 C00F C00E -150.96(13) . . . . ?
O004 N006 C00F C008 -149.28(13) . . . . ?
O004 N006 C00F C00E 30.50(19) . . . . ?
N005 C00A C00I C00C -0.2(2) . . . . ?
N005 C00D C00H C00C 0.8(2) . . . . ?
C007 O001 C00E C00B 3.0(2) . . . . ?
C007 O001 C00E C00F -178.46(12) . . . . ?
C009 C00B C00E O001 179.87(13) . . . . ?
C009 C00B C00E C00F 1.3(2) . . . . ?
C00A N005 C00D O002 179.34(12) . . . . ?
C00A N005 C00D C00H -0.5(2) . . . . ?
C00B C009 C00G O002 174.18(12) . . . . ?
C00B C009 C00G C008 -0.7(2) . . . . ?
C00B C00E C00F N006 179.70(12) . . . . ?
C00B C00E C00F C008 -0.5(2) . . . . ?
C00D O002 C00G C008 -88.77(16) . . . . ?
C00D O002 C00G C009 96.25(16) . . . . ?
C00D N005 C00A C00I 0.2(2) . . . . ?
C00F C008 C00G O002 -173.41(12) . . . . ?
C00F C008 C00G C009 1.5(2) . . . . ?
C00G O002 C00D N005 -0.83(19) . . . . ?
C00G O002 C00D C00H 179.05(12) . . . . ?
C00G C008 C00F N006 178.92(13) . . . . ?
C00G C008 C00F C00E -0.9(2) . . . . ?
C00G C009 C00B C00E -0.7(2) . . . . ?
C00H C00C C00I C00A 0.4(2) . . . . ?
C00I C00C C00H C00D -0.7(2) . . . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.811
_oxdiff_exptl_absorpt_empirical_full_min 0.735
