# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2025

####################################################################### 
# 
# 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_dop033
_database_code_depnum_ccdc_archive 'CCDC 2417392'
loop_
_audit_author_name
_audit_author_address
'Yuqiao Zhou'
;College of Chemistry, Sichuan University, Chengdu, China
China
;
_audit_update_record             
;
2025-01-16 deposited with the CCDC.	2025-05-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H28 F N O2'
_chemical_formula_sum            'C29 H28 F N O2'
_chemical_formula_weight         441.52

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'
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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.5391(3)
_cell_length_b                   21.3461(9)
_cell_length_c                   8.8562(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.5070(10)
_cell_angle_gamma                90
_cell_volume                     1196.77(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9851
_cell_measurement_theta_min      4.14
_cell_measurement_theta_max      79.46

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_F_000             468
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.398
_exptl_crystal_size_mid          0.311
_exptl_crystal_size_min          0.271
_exptl_absorpt_coefficient_mu    0.652
_shelx_estimated_absorpt_T_min   0.781
_shelx_estimated_absorpt_T_max   0.843
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8873
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18209
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.142
_diffrn_reflns_theta_max         79.453
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4990
_reflns_number_gt                4969
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.894
_reflns_Friedel_fraction_max     0.928
_reflns_Friedel_fraction_full    0.991

_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. 
;

_computing_data_collection       'Bruker APEX4'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0392P)²+0.1324P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2325 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.04(2)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4990
_refine_ls_number_parameters     305
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0257
_refine_ls_wR_factor_ref         0.0671
_refine_ls_wR_factor_gt          0.0670
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
F1 F 0.35170(13) 0.55459(4) 0.45428(10) 0.02598(18) Uani 1 1 d . . . . .
O1 O 0.59528(19) 0.47679(6) 0.19331(13) 0.0350(3) Uani 1 1 d . . . . .
O2 O 0.82797(17) 0.47931(5) 0.56006(14) 0.0323(2) Uani 1 1 d . . . . .
N1 N 0.2605(2) 0.51396(6) 0.16464(14) 0.0259(3) Uani 1 1 d D . . . .
H1N H 0.175(3) 0.5318(9) 0.214(2) 0.027(5) Uiso 1 1 d D . . . .
C1 C 0.1614(2) 0.49148(7) 0.00416(17) 0.0278(3) Uani 1 1 d . . . . .
C2 C 0.2743(3) 0.52043(11) -0.1101(2) 0.0441(4) Uani 1 1 d . . . . .
H2A H 0.420604 0.505496 -0.086199 0.066 Uiso 1 1 calc R U . . .
H2B H 0.273175 0.566172 -0.100880 0.066 Uiso 1 1 calc R U . . .
H2C H 0.201624 0.508230 -0.216743 0.066 Uiso 1 1 calc R U . . .
C3 C 0.1705(4) 0.42027(9) -0.0005(2) 0.0469(5) Uani 1 1 d . . . . .
H3A H 0.103184 0.402812 0.077407 0.070 Uiso 1 1 calc R U . . .
H3B H 0.318256 0.406670 0.022681 0.070 Uiso 1 1 calc R U . . .
H3C H 0.095970 0.405481 -0.104441 0.070 Uiso 1 1 calc R U . . .
C4 C -0.0672(3) 0.51350(10) -0.0329(2) 0.0400(4) Uani 1 1 d . . . . .
H4A H -0.134653 0.497697 0.046722 0.060 Uiso 1 1 calc R U . . .
H4B H -0.142948 0.497571 -0.135416 0.060 Uiso 1 1 calc R U . . .
H4C H -0.071280 0.559391 -0.033694 0.060 Uiso 1 1 calc R U . . .
C5 C 0.4615(2) 0.50438(7) 0.24229(16) 0.0246(3) Uani 1 1 d . . . . .
C6 C 0.5288(2) 0.53254(7) 0.40778(17) 0.0234(3) Uani 1 1 d . . . . .
C7 C 0.6759(3) 0.58799(7) 0.40617(18) 0.0284(3) Uani 1 1 d . . . . .
H7A H 0.797357 0.573522 0.367430 0.034 Uiso 1 1 calc R U . . .
H7B H 0.599126 0.619932 0.332357 0.034 Uiso 1 1 calc R U . . .
C8 C 0.7580(3) 0.61800(8) 0.56406(19) 0.0297(3) Uani 1 1 d . . . . .
H8A H 0.858137 0.595320 0.640888 0.036 Uiso 1 1 calc R U . . .
C9 C 0.7004(2) 0.67298(8) 0.60154(17) 0.0275(3) Uani 1 1 d . . . . .
C10 C 0.6504(2) 0.72923(7) 0.63876(18) 0.0276(3) Uani 1 1 d . . . . .
H10A H 0.731993 0.762997 0.615420 0.033 Uiso 1 1 calc R U . . .
C11 C 0.6365(2) 0.47971(7) 0.51888(16) 0.0233(3) Uani 1 1 d . . . . .
C12 C 0.5083(2) 0.42929(7) 0.56731(16) 0.0224(3) Uani 1 1 d . . . . .
C13 C 0.6188(2) 0.38323(7) 0.66741(17) 0.0265(3) Uani 1 1 d . . . . .
H13A H 0.768154 0.386041 0.703185 0.032 Uiso 1 1 calc R U . . .
C14 C 0.5143(2) 0.33365(7) 0.71520(17) 0.0270(3) Uani 1 1 d . . . . .
H14A H 0.592548 0.302940 0.783511 0.032 Uiso 1 1 calc R U . . .
C15 C 0.2937(2) 0.32821(7) 0.66385(16) 0.0230(3) Uani 1 1 d . . . . .
C16 C 0.1842(2) 0.37419(7) 0.56275(17) 0.0251(3) Uani 1 1 d . . . . .
H16A H 0.035060 0.371208 0.525662 0.030 Uiso 1 1 calc R U . . .
C17 C 0.2894(2) 0.42404(7) 0.51572(17) 0.0252(3) Uani 1 1 d . . . . .
H17A H 0.211584 0.454905 0.447695 0.030 Uiso 1 1 calc R U . . .
C21 C 0.1802(2) 0.27508(7) 0.71447(16) 0.0237(3) Uani 1 1 d . . . . .
C22 C 0.2599(3) 0.24642(8) 0.85926(18) 0.0305(3) Uani 1 1 d . . . . .
H22A H 0.388883 0.260790 0.925683 0.037 Uiso 1 1 calc R U . . .
C23 C 0.1524(3) 0.19720(8) 0.90667(19) 0.0350(4) Uani 1 1 d . . . . .
H23A H 0.208149 0.177987 1.005160 0.042 Uiso 1 1 calc R U . . .
C24 C -0.0365(3) 0.17588(8) 0.8107(2) 0.0330(3) Uani 1 1 d . . . . .
H24A H -0.111169 0.142642 0.844223 0.040 Uiso 1 1 calc R U . . .
C25 C -0.1155(3) 0.20320(8) 0.6661(2) 0.0325(3) Uani 1 1 d . . . . .
H25A H -0.243375 0.188179 0.599521 0.039 Uiso 1 1 calc R U . . .
C26 C -0.0083(2) 0.25258(8) 0.61822(18) 0.0287(3) Uani 1 1 d . . . . .
H26A H -0.063765 0.271205 0.518970 0.034 Uiso 1 1 calc R U . . .
C31 C 0.4798(2) 0.74522(7) 0.71331(16) 0.0253(3) Uani 1 1 d . . . . .
C32 C 0.4390(3) 0.80788(7) 0.73949(18) 0.0307(3) Uani 1 1 d . . . . .
H32A H 0.520086 0.839805 0.707332 0.037 Uiso 1 1 calc R U . . .
C33 C 0.2812(3) 0.82420(8) 0.8121(2) 0.0356(4) Uani 1 1 d . . . . .
H33A H 0.254911 0.867057 0.829199 0.043 Uiso 1 1 calc R U . . .
C34 C 0.1623(3) 0.77803(9) 0.8593(2) 0.0363(4) Uani 1 1 d . . . . .
H34A H 0.055304 0.789025 0.909923 0.044 Uiso 1 1 calc R U . . .
C35 C 0.2002(3) 0.71545(8) 0.8323(2) 0.0341(3) Uani 1 1 d . . . . .
H35A H 0.117633 0.683709 0.863649 0.041 Uiso 1 1 calc R U . . .
C36 C 0.3569(2) 0.69910(7) 0.76025(18) 0.0281(3) Uani 1 1 d . . . . .
H36A H 0.381425 0.656182 0.742434 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
F1 C6 1.4039(16) . ?
O1 C5 1.2208(19) . ?
O2 C11 1.2131(19) . ?
N1 C5 1.3380(19) . ?
N1 C1 1.4861(18) . ?
C1 C3 1.522(2) . ?
C1 C4 1.523(2) . ?
C1 C2 1.525(2) . ?
C5 C6 1.5427(19) . ?
C6 C7 1.528(2) . ?
C6 C11 1.546(2) . ?
C7 C8 1.509(2) . ?
C8 C9 1.301(2) . ?
C9 C10 1.308(2) . ?
C10 C31 1.471(2) . ?
C11 C12 1.4917(19) . ?
C12 C17 1.394(2) . ?
C12 C13 1.398(2) . ?
C13 C14 1.382(2) . ?
C14 C15 1.404(2) . ?
C15 C16 1.399(2) . ?
C15 C21 1.485(2) . ?
C16 C17 1.387(2) . ?
C21 C26 1.396(2) . ?
C21 C22 1.398(2) . ?
C22 C23 1.387(2) . ?
C23 C24 1.389(2) . ?
C24 C25 1.384(2) . ?
C25 C26 1.390(2) . ?
C31 C32 1.395(2) . ?
C31 C36 1.398(2) . ?
C32 C33 1.390(3) . ?
C33 C34 1.383(3) . ?
C34 C35 1.390(3) . ?
C35 C36 1.381(2) . ?

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
C5 N1 C1 125.37(13) . . ?
N1 C1 C3 109.73(13) . . ?
N1 C1 C4 105.99(13) . . ?
C3 C1 C4 110.20(15) . . ?
N1 C1 C2 109.66(13) . . ?
C3 C1 C2 110.99(16) . . ?
C4 C1 C2 110.15(14) . . ?
O1 C5 N1 126.19(14) . . ?
O1 C5 C6 117.80(13) . . ?
N1 C5 C6 116.00(12) . . ?
F1 C6 C7 108.10(12) . . ?
F1 C6 C5 110.46(11) . . ?
C7 C6 C5 108.87(12) . . ?
F1 C6 C11 109.63(11) . . ?
C7 C6 C11 112.55(12) . . ?
C5 C6 C11 107.25(11) . . ?
C8 C7 C6 113.51(13) . . ?
C9 C8 C7 124.10(15) . . ?
C8 C9 C10 177.49(16) . . ?
C9 C10 C31 126.25(14) . . ?
O2 C11 C12 121.36(13) . . ?
O2 C11 C6 117.91(13) . . ?
C12 C11 C6 120.67(12) . . ?
C17 C12 C13 118.47(13) . . ?
C17 C12 C11 124.66(13) . . ?
C13 C12 C11 116.84(12) . . ?
C14 C13 C12 121.07(13) . . ?
C13 C14 C15 120.71(13) . . ?
C16 C15 C14 117.96(13) . . ?
C16 C15 C21 120.96(12) . . ?
C14 C15 C21 121.08(13) . . ?
C17 C16 C15 121.17(13) . . ?
C16 C17 C12 120.62(13) . . ?
C26 C21 C22 118.61(14) . . ?
C26 C21 C15 120.66(13) . . ?
C22 C21 C15 120.73(13) . . ?
C23 C22 C21 120.54(14) . . ?
C22 C23 C24 120.25(15) . . ?
C25 C24 C23 119.79(15) . . ?
C24 C25 C26 120.13(15) . . ?
C25 C26 C21 120.67(14) . . ?
C32 C31 C36 118.53(14) . . ?
C32 C31 C10 119.68(14) . . ?
C36 C31 C10 121.79(14) . . ?
C33 C32 C31 120.83(15) . . ?
C34 C33 C32 119.99(16) . . ?
C33 C34 C35 119.65(16) . . ?
C36 C35 C34 120.48(16) . . ?
C35 C36 C31 120.51(15) . . ?

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
C5 N1 C1 C3 60.8(2) . . . . ?
C5 N1 C1 C4 179.79(15) . . . . ?
C5 N1 C1 C2 -61.3(2) . . . . ?
C1 N1 C5 O1 1.3(2) . . . . ?
C1 N1 C5 C6 179.76(13) . . . . ?
O1 C5 C6 F1 -171.68(13) . . . . ?
N1 C5 C6 F1 9.67(17) . . . . ?
O1 C5 C6 C7 69.77(17) . . . . ?
N1 C5 C6 C7 -108.87(14) . . . . ?
O1 C5 C6 C11 -52.27(17) . . . . ?
N1 C5 C6 C11 129.09(13) . . . . ?
F1 C6 C7 C8 61.95(16) . . . . ?
C5 C6 C7 C8 -178.03(13) . . . . ?
C11 C6 C7 C8 -59.27(17) . . . . ?
C6 C7 C8 C9 -109.17(18) . . . . ?
F1 C6 C11 O2 -138.34(13) . . . . ?
C7 C6 C11 O2 -18.00(19) . . . . ?
C5 C6 C11 O2 101.71(15) . . . . ?
F1 C6 C11 C12 44.49(17) . . . . ?
C7 C6 C11 C12 164.83(12) . . . . ?
C5 C6 C11 C12 -75.46(15) . . . . ?
O2 C11 C12 C17 -175.09(14) . . . . ?
C6 C11 C12 C17 2.0(2) . . . . ?
O2 C11 C12 C13 2.6(2) . . . . ?
C6 C11 C12 C13 179.70(13) . . . . ?
C17 C12 C13 C14 -0.3(2) . . . . ?
C11 C12 C13 C14 -178.17(13) . . . . ?
C12 C13 C14 C15 0.2(2) . . . . ?
C13 C14 C15 C16 0.3(2) . . . . ?
C13 C14 C15 C21 179.95(13) . . . . ?
C14 C15 C16 C17 -0.7(2) . . . . ?
C21 C15 C16 C17 179.70(13) . . . . ?
C15 C16 C17 C12 0.5(2) . . . . ?
C13 C12 C17 C16 0.0(2) . . . . ?
C11 C12 C17 C16 177.64(13) . . . . ?
C16 C15 C21 C26 29.2(2) . . . . ?
C14 C15 C21 C26 -150.43(15) . . . . ?
C16 C15 C21 C22 -150.98(15) . . . . ?
C14 C15 C21 C22 29.4(2) . . . . ?
C26 C21 C22 C23 -0.8(2) . . . . ?
C15 C21 C22 C23 179.41(15) . . . . ?
C21 C22 C23 C24 -0.1(3) . . . . ?
C22 C23 C24 C25 1.1(3) . . . . ?
C23 C24 C25 C26 -1.2(3) . . . . ?
C24 C25 C26 C21 0.2(3) . . . . ?
C22 C21 C26 C25 0.7(2) . . . . ?
C15 C21 C26 C25 -179.45(15) . . . . ?
C9 C10 C31 C32 -177.05(15) . . . . ?
C9 C10 C31 C36 3.4(2) . . . . ?
C36 C31 C32 C33 0.6(2) . . . . ?
C10 C31 C32 C33 -178.92(15) . . . . ?
C31 C32 C33 C34 0.0(2) . . . . ?
C32 C33 C34 C35 -0.7(3) . . . . ?
C33 C34 C35 C36 0.7(3) . . . . ?
C34 C35 C36 C31 0.0(2) . . . . ?
C32 C31 C36 C35 -0.6(2) . . . . ?
C10 C31 C36 C35 178.92(15) . . . . ?

_refine_diff_density_max         0.157
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.034



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Et2O'
####################################################################### 
# 
# 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_dop035
_database_code_depnum_ccdc_archive 'CCDC 2417393'
loop_
_audit_author_name
_audit_author_address
'Yuqiao Zhou'
;College of Chemistry, Sichuan University, Chengdu, China
China
;
_audit_update_record             
;
2025-01-16 deposited with the CCDC.	2025-05-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H18 F I N2 O S'
_chemical_formula_sum            'C21 H18 F I N2 O S'
_chemical_formula_weight         492.33

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'
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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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'

_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'

_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. 
;

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                   6.2851(6)
_cell_length_b                   10.2549(9)
_cell_length_c                   30.723(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1980.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9573
_cell_measurement_theta_min      4.55
_cell_measurement_theta_max      68.17

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.651
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.654
_exptl_crystal_size_mid          0.188
_exptl_crystal_size_min          0.104
_exptl_absorpt_coefficient_mu    13.881
_shelx_estimated_absorpt_T_min   0.040
_shelx_estimated_absorpt_T_max   0.326
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.0223
_exptl_absorpt_correction_T_max  0.3475
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9955
_diffrn_reflns_av_unetI/netI     0.0750
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.876
_diffrn_reflns_theta_max         68.165
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_point_group_measured_fraction_full 0.934
_reflns_number_total             3394
_reflns_number_gt                3288
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.601
_reflns_Friedel_fraction_max     0.845
_reflns_Friedel_fraction_full    0.848

_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. 
;

_computing_data_collection       'Bruker APEX5'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0770P)²+0.2822P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1152 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.120(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3394
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1187
_refine_ls_wR_factor_gt          0.1169
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
I I -0.29328(7) 0.44317(6) 0.14339(2) 0.0548(2) Uani 1 1 d . . . . .
S S 0.9575(2) 0.29927(12) 0.38483(5) 0.0335(3) Uani 1 1 d . . . . .
F F 1.0740(6) 0.5584(3) 0.35642(11) 0.0349(7) Uani 1 1 d . . . . .
O O 0.7479(8) 0.7597(4) 0.41553(15) 0.0387(10) Uani 1 1 d . . . . .
N1 N 1.0660(8) 0.6846(4) 0.43888(15) 0.0308(9) Uani 1 1 d . . . . .
N2 N 0.6675(8) 0.4319(5) 0.42585(15) 0.0304(9) Uani 1 1 d . . . . .
C1 C 1.0937(10) 0.7944(6) 0.46878(19) 0.0329(11) Uani 1 1 d . . . . .
H1A H 0.978255 0.857264 0.464472 0.049 Uiso 1 1 calc R U . . .
H1B H 1.230580 0.836790 0.463042 0.049 Uiso 1 1 calc R U . . .
H1C H 1.090915 0.762523 0.498853 0.049 Uiso 1 1 calc R U . . .
C2 C 1.2469(10) 0.5941(6) 0.43895(19) 0.0342(12) Uani 1 1 d . . . . .
H2A H 1.212927 0.518041 0.420922 0.051 Uiso 1 1 calc R U . . .
H2B H 1.275882 0.565661 0.468825 0.051 Uiso 1 1 calc R U . . .
H2C H 1.372707 0.638102 0.427157 0.051 Uiso 1 1 calc R U . . .
C3 C 0.8979(10) 0.6811(5) 0.41314(18) 0.0290(10) Uani 1 1 d . . . . .
C4 C 0.8788(10) 0.5718(5) 0.37821(18) 0.0304(10) Uani 1 1 d . . . . .
C5 C 0.7114(11) 0.6067(5) 0.34392(18) 0.0334(11) Uani 1 1 d . . . . .
H5A H 0.568746 0.609582 0.357558 0.040 Uiso 1 1 calc R U . . .
H5B H 0.742416 0.693894 0.331640 0.040 Uiso 1 1 calc R U . . .
C7 C 0.7137(12) 0.5054(6) 0.30787(19) 0.0368(12) Uani 1 1 d . . . . .
H7 H 0.836735 0.499935 0.289999 0.044 Uiso 1 1 calc R U . . .
C8 C 0.5573(12) 0.4256(7) 0.29999(19) 0.0399(13) Uani 1 1 d . . . . .
C9 C 0.4008(13) 0.3449(6) 0.2903(2) 0.0417(14) Uani 1 1 d . . . . .
H9 H 0.391148 0.266074 0.306412 0.050 Uiso 1 1 calc R U . . .
C10 C 0.2410(11) 0.3680(6) 0.25653(19) 0.0362(13) Uani 1 1 d . . . . .
C11 C 0.2578(11) 0.4733(6) 0.22773(19) 0.0375(13) Uani 1 1 d . . . . .
H11 H 0.373759 0.532043 0.230683 0.045 Uiso 1 1 calc R U . . .
C12 C 0.1110(14) 0.4938(7) 0.1953(2) 0.0424(13) Uani 1 1 d . . . . .
H12 H 0.127697 0.564134 0.175472 0.051 Uiso 1 1 calc R U . . .
C13 C -0.0650(11) 0.4088(7) 0.19183(19) 0.0385(13) Uani 1 1 d . . . . .
C14 C -0.0859(12) 0.3056(7) 0.2198(2) 0.0445(14) Uani 1 1 d . . . . .
H14 H -0.204008 0.248295 0.217233 0.053 Uiso 1 1 calc R U . . .
C15 C 0.0672(12) 0.2848(7) 0.2521(2) 0.0429(14) Uani 1 1 d . . . . .
H15 H 0.052423 0.212698 0.271253 0.052 Uiso 1 1 calc R U . . .
C21 C 0.8246(9) 0.4433(5) 0.39948(17) 0.0280(10) Uani 1 1 d . . . . .
C22 C 0.6346(10) 0.3008(5) 0.43639(17) 0.0294(10) Uani 1 1 d . . . . .
C23 C 0.7783(11) 0.2139(5) 0.41699(17) 0.0299(10) Uani 1 1 d . . . . .
C24 C 0.7597(10) 0.0793(5) 0.42348(18) 0.0337(12) Uani 1 1 d . . . . .
H24 H 0.854546 0.019915 0.409802 0.040 Uiso 1 1 calc R U . . .
C25 C 0.6001(11) 0.0359(5) 0.45026(19) 0.0343(12) Uani 1 1 d . . . . .
H25 H 0.585781 -0.055104 0.455185 0.041 Uiso 1 1 calc R U . . .
C26 C 0.4569(12) 0.1216(6) 0.4707(2) 0.0387(13) Uani 1 1 d . . . . .
H26 H 0.347301 0.088464 0.488846 0.046 Uiso 1 1 calc R U . . .
C27 C 0.4764(11) 0.2548(6) 0.4641(2) 0.0346(12) Uani 1 1 d . . . . .
H27 H 0.382990 0.313871 0.478314 0.042 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
I C13 2.097(6) . ?
S C23 1.735(6) . ?
S C21 1.756(5) . ?
F C4 1.405(7) . ?
O C3 1.243(8) . ?
N1 C3 1.320(8) . ?
N1 C1 1.464(7) . ?
N1 C2 1.468(7) . ?
N2 C21 1.282(8) . ?
N2 C22 1.399(8) . ?
C3 C4 1.556(7) . ?
C4 C21 1.509(7) . ?
C4 C5 1.531(9) . ?
C5 C7 1.518(7) . ?
C7 C8 1.302(11) . ?
C8 C9 1.320(11) . ?
C9 C10 1.463(10) . ?
C10 C15 1.393(10) . ?
C10 C11 1.400(9) . ?
C11 C12 1.374(11) . ?
C12 C13 1.413(11) . ?
C13 C14 1.369(11) . ?
C14 C15 1.398(11) . ?
C22 C27 1.391(9) . ?
C22 C23 1.401(8) . ?
C23 C24 1.400(8) . ?
C24 C25 1.372(9) . ?
C25 C26 1.405(9) . ?
C26 C27 1.386(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
C23 S C21 88.3(3) . . ?
C3 N1 C1 119.5(5) . . ?
C3 N1 C2 127.1(5) . . ?
C1 N1 C2 113.1(5) . . ?
C21 N2 C22 110.4(5) . . ?
O C3 N1 123.7(5) . . ?
O C3 C4 116.7(5) . . ?
N1 C3 C4 119.6(5) . . ?
F C4 C21 108.5(4) . . ?
F C4 C5 107.2(4) . . ?
C21 C4 C5 110.3(5) . . ?
F C4 C3 109.4(5) . . ?
C21 C4 C3 110.3(4) . . ?
C5 C4 C3 111.1(5) . . ?
C7 C5 C4 109.6(5) . . ?
C8 C7 C5 123.9(6) . . ?
C7 C8 C9 177.7(6) . . ?
C8 C9 C10 124.8(6) . . ?
C15 C10 C11 118.0(6) . . ?
C15 C10 C9 120.6(6) . . ?
C11 C10 C9 121.4(6) . . ?
C12 C11 C10 121.7(6) . . ?
C11 C12 C13 119.1(6) . . ?
C14 C13 C12 120.3(6) . . ?
C14 C13 I 120.6(5) . . ?
C12 C13 I 119.0(5) . . ?
C13 C14 C15 119.8(6) . . ?
C10 C15 C14 121.0(6) . . ?
N2 C21 C4 121.8(5) . . ?
N2 C21 S 116.8(4) . . ?
C4 C21 S 121.1(4) . . ?
C27 C22 N2 125.0(5) . . ?
C27 C22 C23 120.4(5) . . ?
N2 C22 C23 114.6(5) . . ?
C24 C23 C22 120.8(6) . . ?
C24 C23 S 129.2(5) . . ?
C22 C23 S 109.9(4) . . ?
C25 C24 C23 117.8(5) . . ?
C24 C25 C26 122.2(5) . . ?
C27 C26 C25 119.7(6) . . ?
C26 C27 C22 119.1(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
C1 N1 C3 O -7.4(8) . . . . ?
C2 N1 C3 O 178.4(6) . . . . ?
C1 N1 C3 C4 174.1(5) . . . . ?
C2 N1 C3 C4 0.0(8) . . . . ?
O C3 C4 F 135.9(5) . . . . ?
N1 C3 C4 F -45.5(7) . . . . ?
O C3 C4 C21 -104.8(6) . . . . ?
N1 C3 C4 C21 73.8(7) . . . . ?
O C3 C4 C5 17.8(7) . . . . ?
N1 C3 C4 C5 -163.6(5) . . . . ?
F C4 C5 C7 54.5(6) . . . . ?
C21 C4 C5 C7 -63.4(7) . . . . ?
C3 C4 C5 C7 173.9(5) . . . . ?
C4 C5 C7 C8 113.6(7) . . . . ?
C8 C9 C10 C15 -172.3(7) . . . . ?
C8 C9 C10 C11 7.9(10) . . . . ?
C15 C10 C11 C12 -1.3(9) . . . . ?
C9 C10 C11 C12 178.4(6) . . . . ?
C10 C11 C12 C13 2.1(10) . . . . ?
C11 C12 C13 C14 -1.6(10) . . . . ?
C11 C12 C13 I 178.4(5) . . . . ?
C12 C13 C14 C15 0.4(10) . . . . ?
I C13 C14 C15 -179.5(5) . . . . ?
C11 C10 C15 C14 0.0(9) . . . . ?
C9 C10 C15 C14 -179.7(6) . . . . ?
C13 C14 C15 C10 0.4(10) . . . . ?
C22 N2 C21 C4 172.2(5) . . . . ?
C22 N2 C21 S -1.4(6) . . . . ?
F C4 C21 N2 171.6(5) . . . . ?
C5 C4 C21 N2 -71.3(6) . . . . ?
C3 C4 C21 N2 51.8(8) . . . . ?
F C4 C21 S -15.1(6) . . . . ?
C5 C4 C21 S 102.1(5) . . . . ?
C3 C4 C21 S -134.9(4) . . . . ?
C23 S C21 N2 1.2(5) . . . . ?
C23 S C21 C4 -172.5(5) . . . . ?
C21 N2 C22 C27 -179.8(6) . . . . ?
C21 N2 C22 C23 1.0(7) . . . . ?
C27 C22 C23 C24 2.9(9) . . . . ?
N2 C22 C23 C24 -177.8(5) . . . . ?
C27 C22 C23 S -179.4(5) . . . . ?
N2 C22 C23 S -0.1(6) . . . . ?
C21 S C23 C24 176.9(6) . . . . ?
C21 S C23 C22 -0.5(4) . . . . ?
C22 C23 C24 C25 -1.6(9) . . . . ?
S C23 C24 C25 -178.8(5) . . . . ?
C23 C24 C25 C26 0.4(9) . . . . ?
C24 C25 C26 C27 -0.5(11) . . . . ?
C25 C26 C27 C22 1.7(11) . . . . ?
N2 C22 C27 C26 177.9(6) . . . . ?
C23 C22 C27 C26 -2.9(10) . . . . ?

_refine_diff_density_max         1.431
_refine_diff_density_min         -0.973
_refine_diff_density_rms         0.138



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EA, PE'
