# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_200828-bxh01-pwy
_database_code_depnum_ccdc_archive 'CCDC 2058418'
loop_
_audit_author_name
_audit_author_address
'yongquan Ning' nenu
_audit_update_record             
;
2021-01-25 deposited with the CCDC.	2021-09-30 downloaded from the CCDC.
;
_audit_creation_date             2020-10-03
_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            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H17 F8 N5 O3'
_chemical_formula_sum            'C19 H17 F8 N5 O3'
_chemical_formula_weight         515.38
_chemical_absolute_configuration ?
_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      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   11.1446(13)
_cell_length_b                   6.5924(9)
_cell_length_c                   29.135(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.968(10)
_cell_angle_gamma                90
_cell_volume                     2135.4(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1152
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.6400
_cell_measurement_theta_min      3.8000
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90668
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
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    1.603
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.859
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            4874
_diffrn_reflns_point_group_measured_fraction_full 0.735
_diffrn_reflns_point_group_measured_fraction_max 0.599
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.212
_diffrn_reflns_theta_min         3.593
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2375
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.859
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -73.00  14.00   1.00   20.00    --   -9.76 -77.00 120.00   87
  2  ω    -81.00  -8.00   1.00   20.00    --   -9.76 -57.00-150.00   73
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0612332000
_diffrn_orient_matrix_UB_12      -0.0183541000
_diffrn_orient_matrix_UB_13      -0.0036953000
_diffrn_orient_matrix_UB_21      0.0144600000
_diffrn_orient_matrix_UB_22      0.0037528000
_diffrn_orient_matrix_UB_23      0.0240994000
_diffrn_orient_matrix_UB_31      -0.0101730000
_diffrn_orient_matrix_UB_32      -0.1059630000
_diffrn_orient_matrix_UB_33      0.0014770000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.290
_reflns_Friedel_fraction_full    0.426
_reflns_Friedel_fraction_max     0.294
_reflns_number_gt                2342
_reflns_number_total             3460
_reflns_odcompleteness_completeness 99.07
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_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         0.304
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 
;
 Flack x determined using 524 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         3460
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0646
_refine_ls_restrained_S_all      1.015
_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)+(0.0864P)²+1.8913P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1551
_refine_ls_wR_factor_ref         0.1818
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00I(H00I)
2.b Secondary CH2 refined with riding coordinates:
 C00J(H00A,H00C), C00K(H00D,H00G), C00L(H00H,H00J), C00M(H00K,H00L), C00Q(H00M,
 H00N), C00R(H00O,H00P)
2.c Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00E(H00E), C00F(H00F), C00X(H00X)
;
_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
F001 F -0.7920(3) -0.1655(6) -0.14309(12) 0.0619(10) Uani 1 1 d . . . . .
N002 N -0.6205(4) 0.0840(7) -0.10030(14) 0.0431(10) Uani 1 1 d . . . . .
O003 O -0.3199(3) -0.5015(7) -0.23993(14) 0.0609(12) Uani 1 1 d . . . . .
O004 O -0.4213(3) -0.7799(7) -0.26155(14) 0.0540(10) Uani 1 1 d . . . . .
N005 N -0.5462(4) -1.0924(7) -0.32543(15) 0.0456(11) Uani 1 1 d . . . . .
N006 N -0.5136(4) -0.5609(7) -0.21954(15) 0.0404(10) Uani 1 1 d . . . . .
O007 O -0.6386(4) 0.3419(8) -0.02323(14) 0.0700(13) Uani 1 1 d . . . . .
F008 F -0.3605(5) -0.8093(8) -0.35759(16) 0.1066(18) Uani 1 1 d . . . . .
C009 C -0.4105(5) -0.6013(9) -0.24015(17) 0.0440(12) Uani 1 1 d . . . . .
C00A C -0.5877(4) -0.0740(8) -0.12994(16) 0.0382(11) Uani 1 1 d . . . . .
C00B C -0.4713(4) -0.1152(9) -0.14204(17) 0.0439(13) Uani 1 1 d . . . . .
H00B H -0.408884 -0.034555 -0.129505 0.053 Uiso 1 1 calc R . . . .
C00C C -0.5351(4) -0.3932(8) -0.19116(16) 0.0375(11) Uani 1 1 d . . . . .
C00D C -0.6750(4) -0.1962(9) -0.15131(17) 0.0399(12) Uani 1 1 d . . . . .
C00E C -0.6532(4) -0.3514(9) -0.18091(17) 0.0406(12) Uani 1 1 d . . . . .
H00E H -0.716517 -0.428368 -0.194077 0.049 Uiso 1 1 calc R . . . .
C00F C -0.4439(4) -0.2683(9) -0.17145(17) 0.0433(12) Uani 1 1 d . . . . .
H00F H -0.364531 -0.289227 -0.178297 0.052 Uiso 1 1 calc R . . . .
N00G N -0.5769(5) -1.2736(9) -0.30834(19) 0.0660(14) Uani 1 1 d . . . . .
F00H F -0.5217(5) -0.8317(10) -0.4068(2) 0.131(2) Uani 1 1 d . . . . .
C00I C -0.5403(5) -0.8643(9) -0.25810(18) 0.0438(12) Uani 1 1 d . . . . .
H00I H -0.535405 -0.987218 -0.239150 0.053 Uiso 1 1 calc R . . . .
C00J C -0.6080(5) -0.7008(9) -0.23430(19) 0.0486(13) Uani 1 1 d . . . . .
H00A H -0.667544 -0.636510 -0.255376 0.058 Uiso 1 1 calc R . . . .
H00C H -0.647356 -0.755002 -0.208293 0.058 Uiso 1 1 calc R . . . .
C00K C -0.5972(5) -0.9130(9) -0.30548(18) 0.0467(13) Uani 1 1 d . . . . .
H00D H -0.682847 -0.933445 -0.303450 0.056 Uiso 1 1 calc R . . . .
H00G H -0.586661 -0.798249 -0.325635 0.056 Uiso 1 1 calc R . . . .
C00L C -0.6777(6) 0.0167(10) -0.0593(2) 0.0596(16) Uani 1 1 d . . . . .
H00H H -0.619347 -0.053042 -0.038674 0.072 Uiso 1 1 calc R . . . .
H00J H -0.742289 -0.077298 -0.067976 0.072 Uiso 1 1 calc R . . . .
C00M C -0.5278(5) 0.2341(10) -0.0870(2) 0.0544(15) Uani 1 1 d . . . . .
H00K H -0.491590 0.283251 -0.114248 0.065 Uiso 1 1 calc R . . . .
H00L H -0.465263 0.171538 -0.066996 0.065 Uiso 1 1 calc R . . . .
F00N F -0.4221(8) -1.1156(12) -0.45184(19) 0.156(3) Uani 1 1 d . . . . .
C00O C -0.4686(7) -1.1208(11) -0.3578(2) 0.0677(18) Uani 1 1 d . . . . .
N00P N -0.5209(6) -1.4169(9) -0.3299(2) 0.0767(17) Uani 1 1 d . . . . .
C00Q C -0.7273(6) 0.1972(11) -0.0351(2) 0.0667(19) Uani 1 1 d . . . . .
H00M H -0.790131 0.259485 -0.055082 0.080 Uiso 1 1 calc R . . . .
H00N H -0.762987 0.151681 -0.007514 0.080 Uiso 1 1 calc R . . . .
C00R C -0.5811(6) 0.4059(11) -0.0629(2) 0.0634(16) Uani 1 1 d . . . . .
H00O H -0.518397 0.502768 -0.053828 0.076 Uiso 1 1 calc R . . . .
H00P H -0.639424 0.473891 -0.083907 0.076 Uiso 1 1 calc R . . . .
F00S F -0.2564(6) -1.1026(13) -0.4007(3) 0.175(4) Uani 1 1 d . . . . .
F00T F -0.2374(10) -0.6978(17) -0.4273(3) 0.200(5) Uani 1 1 d . . . . .
C00U C -0.4199(10) -0.9444(16) -0.3848(3) 0.102(3) Uani 1 1 d . . . . .
C00V C -0.3018(13) -0.828(2) -0.4502(4) 0.116(4) Uani 1 1 d . . . . .
F00W F -0.3806(9) -0.706(2) -0.4692(5) 0.248(7) Uani 1 1 d . . . . .
C00X C -0.4537(7) -1.3246(12) -0.3604(3) 0.077(2) Uani 1 1 d . . . . .
H00X H -0.404595 -1.390421 -0.380199 0.093 Uiso 1 1 calc R . . . .
C00Y C -0.3513(13) -0.992(2) -0.4232(4) 0.130(5) Uani 1 1 d . . . . .
F00Z F -0.2463(14) -0.8867(19) -0.4822(4) 0.279(7) 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
F001 C00D 1.357(5) . ?
N002 C00A 1.416(7) . ?
N002 C00L 1.462(7) . ?
N002 C00M 1.463(7) . ?
O003 C009 1.204(6) . ?
O004 C009 1.334(7) . ?
O004 C00I 1.448(6) . ?
N005 N00G 1.347(7) . ?
N005 C00K 1.451(7) . ?
N005 C00O 1.336(8) . ?
N006 C009 1.359(6) . ?
N006 C00C 1.411(7) . ?
N006 C00J 1.442(7) . ?
O007 C00Q 1.399(8) . ?
O007 C00R 1.425(7) . ?
F008 C00U 1.336(11) . ?
C00A C00B 1.395(7) . ?
C00A C00D 1.378(7) . ?
C00B C00F 1.372(8) . ?
C00C C00E 1.396(7) . ?
C00C C00F 1.401(7) . ?
C00D C00E 1.371(7) . ?
N00G N00P 1.316(8) . ?
F00H C00U 1.467(12) . ?
C00I C00J 1.511(8) . ?
C00I C00K 1.513(7) . ?
C00L C00Q 1.506(9) . ?
C00M C00R 1.478(9) . ?
F00N C00Y 1.373(13) . ?
C00O C00U 1.525(12) . ?
C00O C00X 1.356(10) . ?
N00P C00X 1.345(10) . ?
F00S C00Y 1.407(15) . ?
F00T C00V 1.276(14) . ?
C00U C00Y 1.435(13) . ?
C00V F00W 1.287(16) . ?
C00V C00Y 1.469(15) . ?
C00V F00Z 1.217(13) . ?

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
C00A N002 C00L 114.9(5) . . ?
C00A N002 C00M 116.8(4) . . ?
C00L N002 C00M 109.2(5) . . ?
C009 O004 C00I 111.1(4) . . ?
N00G N005 C00K 117.2(4) . . ?
C00O N005 N00G 109.3(5) . . ?
C00O N005 C00K 133.5(5) . . ?
C009 N006 C00C 126.5(4) . . ?
C009 N006 C00J 111.4(4) . . ?
C00C N006 C00J 121.7(4) . . ?
C00Q O007 C00R 110.5(5) . . ?
O003 C009 O004 122.2(5) . . ?
O003 C009 N006 128.7(5) . . ?
O004 C009 N006 109.1(5) . . ?
C00B C00A N002 125.5(4) . . ?
C00D C00A N002 120.1(4) . . ?
C00D C00A C00B 114.3(5) . . ?
C00F C00B C00A 123.6(5) . . ?
C00E C00C N006 118.7(4) . . ?
C00E C00C C00F 117.7(5) . . ?
C00F C00C N006 123.5(4) . . ?
F001 C00D C00A 119.3(4) . . ?
F001 C00D C00E 115.9(4) . . ?
C00E C00D C00A 124.8(4) . . ?
C00D C00E C00C 119.5(4) . . ?
C00B C00F C00C 120.1(4) . . ?
N00P N00G N005 108.6(5) . . ?
O004 C00I C00J 104.3(4) . . ?
O004 C00I C00K 110.3(4) . . ?
C00J C00I C00K 112.3(4) . . ?
N006 C00J C00I 102.5(4) . . ?
N005 C00K C00I 112.8(4) . . ?
N002 C00L C00Q 109.7(5) . . ?
N002 C00M C00R 110.1(5) . . ?
N005 C00O C00U 121.9(6) . . ?
N005 C00O C00X 105.4(7) . . ?
C00X C00O C00U 132.7(7) . . ?
N00G N00P C00X 107.1(6) . . ?
O007 C00Q C00L 112.3(5) . . ?
O007 C00R C00M 112.1(5) . . ?
F008 C00U F00H 105.0(8) . . ?
F008 C00U C00O 112.5(7) . . ?
F008 C00U C00Y 110.0(9) . . ?
F00H C00U C00O 108.7(7) . . ?
C00Y C00U F00H 102.0(9) . . ?
C00Y C00U C00O 117.5(9) . . ?
F00T C00V F00W 98.5(13) . . ?
F00T C00V C00Y 115.8(11) . . ?
F00W C00V C00Y 114.8(13) . . ?
F00Z C00V F00T 108.5(13) . . ?
F00Z C00V F00W 103.8(14) . . ?
F00Z C00V C00Y 113.8(12) . . ?
N00P C00X C00O 109.6(7) . . ?
F00N C00Y F00S 111.1(12) . . ?
F00N C00Y C00U 106.9(10) . . ?
F00N C00Y C00V 109.5(10) . . ?
F00S C00Y C00U 100.0(9) . . ?
F00S C00Y C00V 109.4(12) . . ?
C00U C00Y C00V 119.6(11) . . ?

_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 1.410
_oxdiff_exptl_absorpt_empirical_full_min 0.784
####################################################################### 
# 
# 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. 
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#######################################################################

data_200827-bxh01-pwy
_database_code_depnum_ccdc_archive 'CCDC 2059785'
loop_
_audit_author_name
_audit_author_address
'yongquan Ning' nenu
_audit_update_record             
;
2021-01-30 deposited with the CCDC.	2021-09-30 downloaded from the CCDC.
;
_audit_creation_date             2021-01-30
_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            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H9 F3 N4 O2 S'
_chemical_formula_sum            'C10 H9 F3 N4 O2 S'
_chemical_formula_weight         306.27
_chemical_absolute_configuration ?
_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'
S S 0.1246 0.1234 '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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.2381(9)
_cell_length_b                   9.2372(19)
_cell_length_c                   28.525(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1380.2(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    504
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.9270
_cell_measurement_theta_min      4.4600
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.275
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
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    1.474
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0929
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.851
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            4410
_diffrn_reflns_point_group_measured_fraction_full 0.900
_diffrn_reflns_point_group_measured_fraction_max 0.741
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.311
_diffrn_reflns_theta_min         3.609
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2375
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.851
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -21.00  15.00   1.00    9.00    --   -9.76 -38.00 150.00   36
  2  ω    -49.00 -16.00   1.00    9.00    --   -9.76 -57.00 -90.00   33
  3  ω    -84.00 -37.00   1.00    9.00    --   -9.76 -38.00 150.00   47
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0064160000
_diffrn_orient_matrix_UB_12      0.0526215000
_diffrn_orient_matrix_UB_13      -0.0180696000
_diffrn_orient_matrix_UB_21      -0.0110093000
_diffrn_orient_matrix_UB_22      0.0554461000
_diffrn_orient_matrix_UB_23      0.0170795000
_diffrn_orient_matrix_UB_31      0.1348318000
_diffrn_orient_matrix_UB_32      0.0070434000
_diffrn_orient_matrix_UB_33      0.0005396000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.483
_reflns_Friedel_fraction_full    0.779
_reflns_Friedel_fraction_max     0.584
_reflns_number_gt                1540
_reflns_number_total             2801
_reflns_odcompleteness_completeness 99.07
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_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         0.366
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 
;
 Flack x determined using 381 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.13(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2801
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1326
_refine_ls_R_factor_gt           0.0662
_refine_ls_restrained_S_all      1.003
_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)+(0.0566P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1236
_refine_ls_wR_factor_ref         0.1555
_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:
 C00B(H00B), C00F(H00F), C00G(H00G), C00H(H00H), C00J(H00J), C00K(H00K)
2.b Idealised Me refined as rotating group:
 C00I(H00A,H00C,H00D)
;
_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
S01 S 0.2570(3) 0.25008(19) 0.57070(5) 0.0501(4) Uani 1 1 d . . . . .
F002 F 0.7852(10) 0.9021(5) 0.54037(17) 0.1000(15) Uani 1 1 d . . . . .
O003 O 0.2304(10) 0.1531(5) 0.53196(14) 0.0759(14) Uani 1 1 d . . . . .
F004 F 0.9835(10) 0.9094(6) 0.60370(16) 0.1123(19) Uani 1 1 d . . . . .
N005 N 0.6123(8) 0.7515(6) 0.63316(16) 0.0494(12) Uani 1 1 d . . . . .
N006 N 0.4744(9) 0.4977(6) 0.57900(16) 0.0515(13) Uani 1 1 d . . . . .
N007 N 0.4363(10) 0.6667(6) 0.65336(16) 0.0522(13) Uani 1 1 d . . . . .
O008 O 0.0410(8) 0.3059(6) 0.59342(16) 0.0804(16) Uani 1 1 d . . . . .
F009 F 1.0841(8) 0.7565(6) 0.55187(18) 0.1158(17) Uani 1 1 d . . . . .
N00A N 0.4234(11) 0.3838(6) 0.54867(17) 0.0583(14) Uani 1 1 d . . . . .
C00B C 0.6420(11) 0.5904(7) 0.5648(2) 0.0497(16) Uani 1 1 d . . . . .
H00B H 0.722158 0.577464 0.536052 0.060 Uiso 1 1 calc R . . . .
C00C C 0.3444(11) 0.7051(6) 0.6981(2) 0.0473(15) Uani 1 1 d . . . . .
C00D C 0.8876(13) 0.8196(8) 0.5731(3) 0.0601(17) Uani 1 1 d . . . . .
C00E C 0.7044(11) 0.7124(6) 0.5932(2) 0.0500(15) Uani 1 1 d . . . . .
C00F C 0.1552(13) 0.7580(9) 0.7868(2) 0.0684(19) Uani 1 1 d . . . . .
H00F H 0.092290 0.775841 0.816712 0.082 Uiso 1 1 calc R . . . .
C00G C 0.4454(13) 0.8150(7) 0.7250(2) 0.0611(18) Uani 1 1 d . . . . .
H00G H 0.577453 0.872139 0.713449 0.073 Uiso 1 1 calc R . . . .
C00H C 0.0531(15) 0.6495(9) 0.7603(2) 0.073(2) Uani 1 1 d . . . . .
H00H H -0.079094 0.593504 0.772324 0.088 Uiso 1 1 calc R . . . .
C00I C 0.4473(15) 0.1665(8) 0.6122(2) 0.079(2) Uani 1 1 d . . . . .
H00A H 0.359757 0.083693 0.624639 0.119 Uiso 1 1 calc GR . . . .
H00C H 0.483578 0.233334 0.637097 0.119 Uiso 1 1 calc GR . . . .
H00D H 0.604315 0.136097 0.597889 0.119 Uiso 1 1 calc GR . . . .
C00J C 0.3478(15) 0.8395(8) 0.7695(2) 0.074(2) Uani 1 1 d . . . . .
H00J H 0.416151 0.913269 0.787775 0.089 Uiso 1 1 calc R . . . .
C00K C 0.1448(14) 0.6223(8) 0.7157(2) 0.070(2) Uani 1 1 d . . . . .
H00K H 0.073321 0.548985 0.697585 0.084 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
S01 O003 1.429(4) . ?
S01 O008 1.402(5) . ?
S01 N00A 1.637(5) . ?
S01 C00I 1.729(7) . ?
F002 C00D 1.318(8) . ?
F004 C00D 1.306(8) . ?
N005 N007 1.340(6) . ?
N005 C00E 1.289(7) . ?
N006 N00A 1.388(6) . ?
N006 C00B 1.291(7) . ?
N007 C00C 1.410(7) . ?
F009 C00D 1.329(8) . ?
C00B C00E 1.426(8) . ?
C00C C00G 1.378(8) . ?
C00C C00K 1.389(9) . ?
C00D C00E 1.493(9) . ?
C00F C00H 1.364(10) . ?
C00F C00J 1.352(10) . ?
C00G C00J 1.387(9) . ?
C00H C00K 1.383(9) . ?

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
O003 S01 N00A 103.2(3) . . ?
O003 S01 C00I 107.8(3) . . ?
O008 S01 O003 120.6(3) . . ?
O008 S01 N00A 109.2(3) . . ?
O008 S01 C00I 108.2(4) . . ?
N00A S01 C00I 107.0(3) . . ?
C00E N005 N007 118.3(5) . . ?
C00B N006 N00A 116.0(5) . . ?
N005 N007 C00C 118.5(5) . . ?
N006 N00A S01 115.8(4) . . ?
N006 C00B C00E 120.2(5) . . ?
C00G C00C N007 123.9(6) . . ?
C00G C00C C00K 119.6(6) . . ?
C00K C00C N007 116.4(6) . . ?
F002 C00D F009 104.3(6) . . ?
F002 C00D C00E 113.2(6) . . ?
F004 C00D F002 105.2(6) . . ?
F004 C00D F009 106.6(6) . . ?
F004 C00D C00E 114.3(6) . . ?
F009 C00D C00E 112.4(6) . . ?
N005 C00E C00B 129.5(6) . . ?
N005 C00E C00D 113.3(6) . . ?
C00B C00E C00D 117.0(6) . . ?
C00J C00F C00H 120.0(6) . . ?
C00C C00G C00J 119.2(7) . . ?
C00F C00H C00K 120.5(7) . . ?
C00F C00J C00G 121.2(7) . . ?
C00H C00K C00C 119.5(7) . . ?

_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 1.125
_oxdiff_exptl_absorpt_empirical_full_min 0.891
