# Electronic Supplementary Material (ESI) for RSC Medicinal Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_sz02
_database_code_depnum_ccdc_archive 'CCDC 2335488'
loop_
_audit_author_name
_audit_author_address
'Farzaneh Fadaei Tirani'
;EPFL
Switzerland
;
_audit_update_record             
;
2024-02-26 deposited with the CCDC.	2024-05-21 downloaded from the CCDC.
;
_audit_creation_date             2018-12-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H29 Cl2 F13 N2 O4'
_chemical_formula_sum            'C26 H29 Cl2 F13 N2 O4'
_chemical_formula_weight         751.41
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C26 H29 N2 O4 F13 Cl2'
_chemical_oxdiff_usercomment     'black crystal'
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'
Cl Cl 0.3639 0.7018 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   10.97900(20)
_cell_length_b                   30.0354(5)
_cell_length_c                   9.7195(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3205.10(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    18070
_cell_measurement_temperature    140.01(10)
_cell_measurement_theta_max      74.6190
_cell_measurement_theta_min      4.2380
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.855
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.534
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2018).
 Numerical absorption correction based on Gaussian integration over
 a multifaceted crystal model/Empirical absorption correction using
 spherical harmonics as implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1528
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -19 0 0.0197
-1 19 0 0.0077
-7 1 0 0.0521
7 -1 0 0.0411
-1 1 6 0.1888
4 4 5 0.1371
-4 -4 -5 0.3631

_exptl_crystal_size_max          0.678
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.027
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0000 -18.9994 0.0000 -0.1219 -0.9765 0.0166
-1.0000 18.9994 -0.0000 0.1219 0.9765 -0.0166
-7.0000 1.0002 0.0000 -0.9014 0.3002 -0.2533
7.0000 -1.0002 -0.0000 0.9014 -0.3002 0.2533
-1.0000 1.0013 6.0000 -0.3596 0.1316 0.8839
4.0000 4.0008 5.0000 0.3740 0.0933 0.9154
-4.0000 -4.0008 -5.0000 -0.3740 -0.0933 -0.9154

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            57908
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.376
_diffrn_reflns_theta_min         4.288
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2665
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      5.00  30.00   1.00    5.00    --   42.00  89.00-103.04   25
  2  ω   -115.00 -15.00   1.00    5.00    --  -43.13 -57.00 -90.00  100
  3  ω   -112.00 -18.00   1.00    5.00    --  -43.13 -57.00-180.00   94
  4  ω   -117.00 -19.00   1.00    5.00    --  -43.13 -37.00   0.00   98
  5  ω    -70.00  29.00   1.00    5.00    --  -43.13  57.00 -30.00   99
  6  ω     69.00 104.00   1.00    5.00    --   43.13  66.00  -5.63   35
  7  ω     13.00  39.00   1.00    5.00    --   43.13  66.00  -5.63   26
  8  ω     31.00  99.00   1.00    5.00    --   43.13-125.00-150.00   68
  9  ω     11.00  36.00   1.00    5.00    --   46.00  84.00  15.80   25
 10  ω     11.00  36.00   1.00    5.00    --   46.00  84.00  89.44   25
 11  ω     17.00  42.00   1.00    5.00    --   50.00  80.00  85.85   25
 12  ω     20.00  46.00   1.00    5.00    --   54.00  81.00 -33.27   26
 13  ω     20.00  45.00   1.00    5.00    --   54.00  81.00 -92.12   25
 14  ω     20.00  45.00   1.00    5.00    --   54.00  81.00 151.51   25
 15  ω     20.00  45.00   1.00    5.00    --   54.00  81.00-149.23   25
 16  ω     30.00  57.00   1.00    5.00    --   62.00  75.00  34.10   27
 17  ω     33.00  59.00   1.00    5.00    --   66.00  77.00-101.07   26
 18  ω     33.00  62.00   1.00    5.00    --   66.00  77.00 101.96   29
 19  ω     36.00  62.00   1.00    5.00    --   66.00  65.00  79.36   26
 20  ω     38.00  65.00   1.00    5.00    --   70.00  77.00  78.24   27
 21  ω     38.00  65.00   1.00    5.00    --   70.00  75.00-167.86   27
 22  ω     91.00 144.00   1.00    5.00    --   70.00  77.00 -60.88   53
 23  ω     37.00  63.00   1.00    5.00    --   70.00  77.00 -60.88   26
 24  ω     43.00  70.00   1.00    5.00    --   74.00  77.00 -47.96   27
 25  ω     42.00  68.00   1.00    5.00    --   74.00  76.00-140.85   26
 26  ω     41.00  67.00   1.00    5.00    --   74.00  77.00 149.92   26
 27  ω    111.00 150.00   1.00    5.00    --   74.00  76.00-140.85   39
 28  ω    126.00 153.00   1.00   20.00    --   78.00  77.00 154.12   27
 29  ω     48.00  74.00   1.00   20.00    --   78.00  77.00 154.12   26
 30  ω     47.00  73.00   1.00   20.00    --   78.00  70.00  17.71   26
 31  ω     50.00  76.00   1.00   20.00    --   82.00  73.00 -24.18   26
 32  ω     55.00  82.00   1.00   20.00    --   82.00  64.00-118.70   27
 33  ω     58.00  83.00   1.00   20.00    --   86.00  59.00 -59.41   25
 34  ω     54.00  80.00   1.00   20.00    --   86.00  74.00 118.16   26
 35  ω     59.00  85.00   1.00   20.00    --   90.00  71.00-105.80   26
 36  ω     58.00  84.00   1.00   20.00    --   90.00  74.00  34.12   26
 37  ω     62.00  93.00   1.00   20.00    --   94.00  76.00  76.30   31
 38  ω     97.00 168.00   1.00   20.00    --   94.00  75.00 172.06   71
 39  ω     62.00  88.00   1.00   20.00    --   94.00  75.00 172.06   26
 40  ω     66.00 136.00   1.00   20.00    --   98.00  74.00-163.52   70
 41  ω    122.00 170.00   1.00   20.00    --   98.00  69.00 124.99   48
 42  ω     67.00  94.00   1.00   20.00    --   98.00  69.00 124.99   27
 43  ω     67.00 157.00   1.00   20.00    --   98.00  69.00  14.34   90
 44  ω    148.00 173.00   1.00   20.00    --   98.00  74.00-163.52   25
 45  ω    134.00 178.00   1.00   20.00    --  109.26 111.00   0.00   44
 46  ω     80.00 161.00   1.00   20.00    --  109.26  61.00  60.00   81
 47  ω     78.00 149.00   1.00   20.00    --  109.26  77.00-150.00   71
 48  ω     79.00 175.00   1.00   20.00    --  109.26  77.00-120.00   96
 49  ω     78.00 162.00   1.00   20.00    --  109.26  77.00 -60.00   84
 50  ω    138.00 178.00   1.00   20.00    --  109.26  77.00  30.00   40
 51  ω     77.00 103.00   1.00   20.00    --  109.26  77.00  30.00   26
 52  ω     77.00 178.00   1.00   20.00    --  109.26  77.00 -90.00  101
 53  ω     78.00 171.00   1.00   20.00    --  109.26  77.00  90.00   93
 54  ω     81.00 174.00   1.00   20.00    --  109.26  61.00 150.00   93
 55  ω     34.00 138.00   1.00   20.00    --  109.26 -77.00  60.00  104
 56  ω    150.00 177.00   1.00   20.00    --  109.26 111.00  90.00   27
 57  ω     77.00 178.00   1.00   20.00    --  109.26  77.00 -30.00  101
 58  ω     33.00 104.00   1.00   20.00    --  109.26 -94.00 -60.00   71
 59  ω     43.00 108.00   1.00   20.00    --  109.26 -94.00  30.00   65
 60  ω     60.00 116.00   1.00   20.00    --  109.26-111.00-120.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1306674000
_diffrn_orient_matrix_UB_12      0.0132937000
_diffrn_orient_matrix_UB_13      -0.0403779000
_diffrn_orient_matrix_UB_21      -0.0358124000
_diffrn_orient_matrix_UB_22      0.0495100000
_diffrn_orient_matrix_UB_23      0.0077027000
_diffrn_orient_matrix_UB_31      0.0363289000
_diffrn_orient_matrix_UB_32      0.0010361000
_diffrn_orient_matrix_UB_33      0.1531951000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.845
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.953
_reflns_number_gt                5851
_reflns_number_total             6448
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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         0.313
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 2483 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.003(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     431
_refine_ls_number_reflns         6448
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0370
_refine_ls_restrained_S_all      1.026
_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)+(0.0550P)²+0.9320P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0912
_refine_ls_wR_factor_ref         0.0961
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C16(H16A,H16B), C23(H23A,H23B), C24(H24A,H24B),
 C25(H25A,H25B), C26(H26A,H26B)
2.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C19(H19), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
Cl1 Cl 0.35293(14) 0.08317(4) 0.02338(17) 0.0825(5) Uani 1 1 d . . . . .
Cl2 Cl 0.24923(14) 0.31423(3) 0.08779(15) 0.0675(3) Uani 1 1 d . . . . .
F1 F 0.58034(17) 0.33160(6) 0.7884(3) 0.0445(5) Uani 1 1 d . . . . .
F2 F 0.61155(19) 0.36761(7) 0.5976(2) 0.0431(5) Uani 1 1 d . . . . .
F3 F 0.6252(2) 0.40077(7) 0.9417(2) 0.0427(5) Uani 1 1 d . . . . .
F4 F 0.48750(17) 0.41319(7) 0.7842(3) 0.0446(5) Uani 1 1 d . . . . .
F5 F 0.6844(2) 0.45248(7) 0.6288(2) 0.0439(5) Uani 1 1 d . . . . .
F6 F 0.78707(16) 0.44922(6) 0.8190(3) 0.0415(5) Uani 1 1 d . . . . .
F7 F 0.5699(2) 0.48777(7) 0.9439(2) 0.0488(6) Uani 1 1 d . . . . .
F8 F 0.51602(19) 0.50240(7) 0.7323(3) 0.0485(6) Uani 1 1 d . . . . .
F9 F 0.7740(2) 0.53199(7) 0.9198(2) 0.0475(5) Uani 1 1 d . . . . .
F10 F 0.7581(2) 0.53678(7) 0.6991(2) 0.0411(5) Uani 1 1 d . . . . .
F11 F 0.5517(3) 0.57882(9) 0.9356(4) 0.0981(13) Uani 1 1 d . . . . .
F12 F 0.5668(3) 0.58999(9) 0.7177(4) 0.0840(10) Uani 1 1 d . . . . .
F13 F 0.7092(3) 0.61215(8) 0.8521(3) 0.0699(8) Uani 1 1 d . . . . .
O1 O 0.85113(19) 0.22740(7) 0.5907(2) 0.0289(5) Uani 1 1 d . . . . .
O2 O 0.7716(2) 0.27466(7) 0.7455(2) 0.0286(4) Uani 1 1 d . . . . .
O3 O 0.7289(2) 0.12410(7) 0.9431(2) 0.0289(5) Uani 1 1 d . . . . .
O4 O 0.81628(19) 0.08446(7) 0.7690(2) 0.0270(4) Uani 1 1 d . . . . .
N1 N 0.7703(2) 0.15518(8) 0.7360(3) 0.0234(5) Uani 1 1 d . . . . .
H1 H 0.783(3) 0.1511(10) 0.657(4) 0.011(8) Uiso 1 1 d . . . . .
N2 N 0.3709(3) 0.19752(9) 0.2372(3) 0.0352(6) Uani 1 1 d . . . . .
C1 C 0.7304(3) 0.19890(9) 0.7797(3) 0.0236(6) Uani 1 1 d . . . . .
H1A H 0.756216 0.203156 0.877536 0.028 Uiso 1 1 calc R . . . .
C2 C 0.7928(3) 0.23373(10) 0.6939(3) 0.0233(6) Uani 1 1 d . . . . .
C3 C 0.8165(3) 0.31107(10) 0.6640(4) 0.0313(7) Uani 1 1 d . . . . .
H3A H 0.779705 0.310372 0.571076 0.038 Uiso 1 1 calc R . . . .
H3B H 0.906128 0.309021 0.654329 0.038 Uiso 1 1 calc R . . . .
C4 C 0.7818(3) 0.35390(10) 0.7379(4) 0.0291(6) Uani 1 1 d . . . . .
H4A H 0.806052 0.351433 0.835732 0.035 Uiso 1 1 calc R . . . .
H4B H 0.828191 0.378886 0.697051 0.035 Uiso 1 1 calc R . . . .
C5 C 0.6481(3) 0.36450(10) 0.7307(4) 0.0307(7) Uani 1 1 d . . . . .
C6 C 0.6076(3) 0.40748(10) 0.8058(4) 0.0311(7) Uani 1 1 d . . . . .
C7 C 0.6738(3) 0.45077(10) 0.7650(4) 0.0299(6) Uani 1 1 d . . . . .
C8 C 0.6108(3) 0.49430(10) 0.8159(4) 0.0327(7) Uani 1 1 d . . . . .
C9 C 0.6954(3) 0.53538(11) 0.8158(4) 0.0339(7) Uani 1 1 d . . . . .
C10 C 0.6280(4) 0.58025(12) 0.8308(6) 0.0565(12) Uani 1 1 d . . . . .
C11 C 0.7679(2) 0.12138(9) 0.8266(3) 0.0235(6) Uani 1 1 d . . . . .
C12 C 0.8164(3) 0.04181(10) 0.8445(3) 0.0283(6) Uani 1 1 d . . . . .
C13 C 0.8925(3) 0.04593(11) 0.9752(4) 0.0345(7) Uani 1 1 d . . . . .
H13A H 0.973150 0.057754 0.951993 0.052 Uiso 1 1 calc GR . . . .
H13B H 0.901442 0.016535 1.017756 0.052 Uiso 1 1 calc GR . . . .
H13C H 0.851916 0.066144 1.039653 0.052 Uiso 1 1 calc GR . . . .
C14 C 0.8768(4) 0.01066(11) 0.7437(4) 0.0396(8) Uani 1 1 d . . . . .
H14A H 0.824759 0.007196 0.662433 0.059 Uiso 1 1 calc GR . . . .
H14B H 0.889106 -0.018425 0.787166 0.059 Uiso 1 1 calc GR . . . .
H14C H 0.955674 0.022989 0.715912 0.059 Uiso 1 1 calc GR . . . .
C15 C 0.6863(3) 0.02776(12) 0.8732(4) 0.0378(8) Uani 1 1 d . . . . .
H15A H 0.649487 0.048356 0.939460 0.057 Uiso 1 1 calc GR . . . .
H15B H 0.685693 -0.002448 0.911353 0.057 Uiso 1 1 calc GR . . . .
H15C H 0.639439 0.028270 0.787380 0.057 Uiso 1 1 calc GR . . . .
C16 C 0.5909(3) 0.20496(10) 0.7725(3) 0.0261(6) Uani 1 1 d . . . . .
H16A H 0.551881 0.181678 0.829552 0.031 Uiso 1 1 calc R . . . .
H16B H 0.569624 0.234205 0.812849 0.031 Uiso 1 1 calc R . . . .
C17 C 0.5389(2) 0.20252(10) 0.6288(3) 0.0250(6) Uani 1 1 d . . . . .
C18 C 0.5010(3) 0.16266(10) 0.5715(3) 0.0271(6) Uani 1 1 d . . . . .
H18 H 0.511445 0.135945 0.622528 0.033 Uiso 1 1 calc R . . . .
C19 C 0.4481(3) 0.16048(10) 0.4419(3) 0.0290(6) Uani 1 1 d . . . . .
H19 H 0.423465 0.132432 0.406328 0.035 Uiso 1 1 calc R . . . .
C20 C 0.4304(3) 0.19873(10) 0.3630(3) 0.0273(6) Uani 1 1 d . . . . .
C21 C 0.4728(3) 0.23902(10) 0.4182(3) 0.0281(6) Uani 1 1 d . . . . .
H21 H 0.465399 0.265649 0.366142 0.034 Uiso 1 1 calc R . . . .
C22 C 0.5256(3) 0.24044(10) 0.5483(3) 0.0266(6) Uani 1 1 d . . . . .
H22 H 0.553412 0.268188 0.583130 0.032 Uiso 1 1 calc R . . . .
C23 C 0.3234(3) 0.15645(12) 0.1811(4) 0.0378(8) Uani 1 1 d . . . . .
H23A H 0.255576 0.163272 0.117379 0.045 Uiso 1 1 calc R . . . .
H23B H 0.290753 0.137893 0.256728 0.045 Uiso 1 1 calc R . . . .
C24 C 0.4209(4) 0.13057(13) 0.1047(4) 0.0440(8) Uani 1 1 d . . . . .
H24A H 0.484705 0.120706 0.169857 0.053 Uiso 1 1 calc R . . . .
H24B H 0.459459 0.149853 0.034479 0.053 Uiso 1 1 calc R . . . .
C25 C 0.3609(3) 0.23691(12) 0.1513(4) 0.0375(8) Uani 1 1 d . . . . .
H25A H 0.349569 0.227751 0.054243 0.045 Uiso 1 1 calc R . . . .
H25B H 0.437329 0.254269 0.157240 0.045 Uiso 1 1 calc R . . . .
C26 C 0.2550(4) 0.26598(13) 0.1948(5) 0.0448(9) Uani 1 1 d . . . . .
H26A H 0.265197 0.274997 0.292141 0.054 Uiso 1 1 calc R . . . .
H26B H 0.177916 0.249096 0.186694 0.054 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
Cl1 C24 1.791(4) . ?
Cl2 C26 1.785(4) . ?
F1 C5 1.358(4) . ?
F2 C5 1.358(4) . ?
F3 C6 1.350(4) . ?
F4 C6 1.346(4) . ?
F5 C7 1.330(4) . ?
F6 C7 1.351(4) . ?
F7 C8 1.337(4) . ?
F8 C8 1.343(4) . ?
F9 C9 1.333(4) . ?
F10 C9 1.327(4) . ?
F11 C10 1.319(6) . ?
F12 C10 1.321(6) . ?
F13 C10 1.325(5) . ?
O1 C2 1.206(4) . ?
O2 C2 1.348(4) . ?
O2 C3 1.437(4) . ?
O3 C11 1.213(4) . ?
O4 C11 1.351(3) . ?
O4 C12 1.476(3) . ?
N1 H1 0.79(4) . ?
N1 C1 1.448(4) . ?
N1 C11 1.344(4) . ?
N2 C20 1.387(4) . ?
N2 C23 1.446(4) . ?
N2 C25 1.453(5) . ?
C1 H1A 1.0000 . ?
C1 C2 1.503(4) . ?
C1 C16 1.544(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.522(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.504(4) . ?
C5 C6 1.548(4) . ?
C6 C7 1.542(4) . ?
C7 C8 1.560(4) . ?
C8 C9 1.544(4) . ?
C9 C10 1.545(5) . ?
C12 C13 1.525(5) . ?
C12 C14 1.508(5) . ?
C12 C15 1.515(5) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.510(4) . ?
C17 C18 1.385(4) . ?
C17 C22 1.390(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.389(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.395(4) . ?
C20 C21 1.403(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.392(4) . ?
C22 H22 0.9500 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.517(5) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.514(6) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?

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
C2 O2 C3 115.5(2) . . ?
C11 O4 C12 120.4(2) . . ?
C1 N1 H1 119(2) . . ?
C11 N1 H1 121(2) . . ?
C11 N1 C1 119.1(3) . . ?
C20 N2 C23 121.7(3) . . ?
C20 N2 C25 121.4(3) . . ?
C23 N2 C25 116.8(3) . . ?
N1 C1 H1A 108.0 . . ?
N1 C1 C2 109.3(2) . . ?
N1 C1 C16 113.2(2) . . ?
C2 C1 H1A 108.0 . . ?
C2 C1 C16 110.2(2) . . ?
C16 C1 H1A 108.0 . . ?
O1 C2 O2 123.0(3) . . ?
O1 C2 C1 126.5(3) . . ?
O2 C2 C1 110.5(2) . . ?
O2 C3 H3A 110.3 . . ?
O2 C3 H3B 110.3 . . ?
O2 C3 C4 107.3(3) . . ?
H3A C3 H3B 108.5 . . ?
C4 C3 H3A 110.3 . . ?
C4 C3 H3B 110.3 . . ?
C3 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C5 C4 C3 113.7(3) . . ?
C5 C4 H4A 108.8 . . ?
C5 C4 H4B 108.8 . . ?
F1 C5 C4 111.2(2) . . ?
F1 C5 C6 104.7(3) . . ?
F2 C5 F1 106.3(3) . . ?
F2 C5 C4 110.3(3) . . ?
F2 C5 C6 107.9(2) . . ?
C4 C5 C6 115.8(3) . . ?
F3 C6 C5 107.2(3) . . ?
F3 C6 C7 108.1(3) . . ?
F4 C6 F3 108.2(3) . . ?
F4 C6 C5 108.3(3) . . ?
F4 C6 C7 108.3(2) . . ?
C7 C6 C5 116.5(3) . . ?
F5 C7 F6 107.9(3) . . ?
F5 C7 C6 109.3(3) . . ?
F5 C7 C8 108.8(3) . . ?
F6 C7 C6 107.8(3) . . ?
F6 C7 C8 108.3(3) . . ?
C6 C7 C8 114.6(3) . . ?
F7 C8 F8 109.2(3) . . ?
F7 C8 C7 108.7(3) . . ?
F7 C8 C9 108.7(3) . . ?
F8 C8 C7 107.7(3) . . ?
F8 C8 C9 108.7(3) . . ?
C9 C8 C7 113.8(3) . . ?
F9 C9 C8 109.1(3) . . ?
F9 C9 C10 107.8(3) . . ?
F10 C9 F9 108.4(3) . . ?
F10 C9 C8 109.8(3) . . ?
F10 C9 C10 107.6(3) . . ?
C8 C9 C10 114.1(3) . . ?
F11 C10 F12 109.1(4) . . ?
F11 C10 F13 109.2(4) . . ?
F11 C10 C9 110.4(4) . . ?
F12 C10 F13 108.2(4) . . ?
F12 C10 C9 111.0(4) . . ?
F13 C10 C9 108.8(3) . . ?
O3 C11 O4 125.5(3) . . ?
O3 C11 N1 124.6(3) . . ?
N1 C11 O4 109.9(3) . . ?
O4 C12 C13 110.1(2) . . ?
O4 C12 C14 102.4(2) . . ?
O4 C12 C15 109.4(2) . . ?
C14 C12 C13 110.5(3) . . ?
C14 C12 C15 111.2(3) . . ?
C15 C12 C13 112.7(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1 C16 H16A 108.7 . . ?
C1 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
C17 C16 C1 114.3(2) . . ?
C17 C16 H16A 108.7 . . ?
C17 C16 H16B 108.7 . . ?
C18 C17 C16 121.8(3) . . ?
C18 C17 C22 116.8(3) . . ?
C22 C17 C16 121.4(3) . . ?
C17 C18 H18 119.0 . . ?
C17 C18 C19 122.1(3) . . ?
C19 C18 H18 119.0 . . ?
C18 C19 H19 119.4 . . ?
C18 C19 C20 121.2(3) . . ?
C20 C19 H19 119.4 . . ?
N2 C20 C19 121.9(3) . . ?
N2 C20 C21 121.1(3) . . ?
C19 C20 C21 117.0(3) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 C20 120.8(3) . . ?
C22 C21 H21 119.6 . . ?
C17 C22 C21 122.0(3) . . ?
C17 C22 H22 119.0 . . ?
C21 C22 H22 119.0 . . ?
N2 C23 H23A 109.3 . . ?
N2 C23 H23B 109.3 . . ?
N2 C23 C24 111.6(3) . . ?
H23A C23 H23B 108.0 . . ?
C24 C23 H23A 109.3 . . ?
C24 C23 H23B 109.3 . . ?
Cl1 C24 H24A 109.8 . . ?
Cl1 C24 H24B 109.8 . . ?
C23 C24 Cl1 109.2(3) . . ?
C23 C24 H24A 109.8 . . ?
C23 C24 H24B 109.8 . . ?
H24A C24 H24B 108.3 . . ?
N2 C25 H25A 109.3 . . ?
N2 C25 H25B 109.3 . . ?
N2 C25 C26 111.5(3) . . ?
H25A C25 H25B 108.0 . . ?
C26 C25 H25A 109.3 . . ?
C26 C25 H25B 109.3 . . ?
Cl2 C26 H26A 109.8 . . ?
Cl2 C26 H26B 109.8 . . ?
C25 C26 Cl2 109.4(3) . . ?
C25 C26 H26A 109.8 . . ?
C25 C26 H26B 109.8 . . ?
H26A C26 H26B 108.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O3 0.79(4) 2.24(4) 2.996(3) 162(3) 4_654 yes

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
F1 C5 C6 F3 56.6(3) . . . . ?
F1 C5 C6 F4 -60.0(3) . . . . ?
F1 C5 C6 C7 177.7(3) . . . . ?
F2 C5 C6 F3 169.5(2) . . . . ?
F2 C5 C6 F4 53.0(3) . . . . ?
F2 C5 C6 C7 -69.3(3) . . . . ?
F3 C6 C7 F5 164.5(2) . . . . ?
F3 C6 C7 F6 47.5(3) . . . . ?
F3 C6 C7 C8 -73.2(3) . . . . ?
F4 C6 C7 F5 -78.5(3) . . . . ?
F4 C6 C7 F6 164.5(3) . . . . ?
F4 C6 C7 C8 43.8(4) . . . . ?
F5 C7 C8 F7 163.1(3) . . . . ?
F5 C7 C8 F8 44.9(3) . . . . ?
F5 C7 C8 C9 -75.7(4) . . . . ?
F6 C7 C8 F7 -79.9(3) . . . . ?
F6 C7 C8 F8 161.9(3) . . . . ?
F6 C7 C8 C9 41.4(4) . . . . ?
F7 C8 C9 F9 47.6(3) . . . . ?
F7 C8 C9 F10 166.2(3) . . . . ?
F7 C8 C9 C10 -73.0(4) . . . . ?
F8 C8 C9 F9 166.3(3) . . . . ?
F8 C8 C9 F10 -75.1(3) . . . . ?
F8 C8 C9 C10 45.7(4) . . . . ?
F9 C9 C10 F11 -71.4(4) . . . . ?
F9 C9 C10 F12 167.4(3) . . . . ?
F9 C9 C10 F13 48.5(5) . . . . ?
F10 C9 C10 F11 171.9(4) . . . . ?
F10 C9 C10 F12 50.8(4) . . . . ?
F10 C9 C10 F13 -68.2(5) . . . . ?
O2 C3 C4 C5 -72.2(3) . . . . ?
N1 C1 C2 O1 11.3(4) . . . . ?
N1 C1 C2 O2 -170.9(2) . . . . ?
N1 C1 C16 C17 -64.3(3) . . . . ?
N2 C20 C21 C22 175.9(3) . . . . ?
N2 C23 C24 Cl1 -174.2(3) . . . . ?
N2 C25 C26 Cl2 178.9(2) . . . . ?
C1 N1 C11 O3 3.6(4) . . . . ?
C1 N1 C11 O4 -175.7(2) . . . . ?
C1 C16 C17 C18 89.9(3) . . . . ?
C1 C16 C17 C22 -90.9(3) . . . . ?
C2 O2 C3 C4 179.1(2) . . . . ?
C2 C1 C16 C17 58.3(3) . . . . ?
C3 O2 C2 O1 3.9(4) . . . . ?
C3 O2 C2 C1 -174.0(2) . . . . ?
C3 C4 C5 F1 59.9(4) . . . . ?
C3 C4 C5 F2 -57.8(3) . . . . ?
C3 C4 C5 C6 179.3(3) . . . . ?
C4 C5 C6 F3 -66.3(3) . . . . ?
C4 C5 C6 F4 177.2(3) . . . . ?
C4 C5 C6 C7 54.8(4) . . . . ?
C5 C6 C7 F5 43.8(4) . . . . ?
C5 C6 C7 F6 -73.2(3) . . . . ?
C5 C6 C7 C8 166.2(3) . . . . ?
C6 C7 C8 F7 40.4(4) . . . . ?
C6 C7 C8 F8 -77.8(3) . . . . ?
C6 C7 C8 C9 161.7(3) . . . . ?
C7 C8 C9 F9 -73.7(4) . . . . ?
C7 C8 C9 F10 44.9(4) . . . . ?
C7 C8 C9 C10 165.7(3) . . . . ?
C8 C9 C10 F11 49.9(5) . . . . ?
C8 C9 C10 F12 -71.2(4) . . . . ?
C8 C9 C10 F13 169.8(4) . . . . ?
C11 O4 C12 C13 -62.8(4) . . . . ?
C11 O4 C12 C14 179.6(3) . . . . ?
C11 O4 C12 C15 61.6(3) . . . . ?
C11 N1 C1 C2 153.4(3) . . . . ?
C11 N1 C1 C16 -83.4(3) . . . . ?
C12 O4 C11 O3 4.9(4) . . . . ?
C12 O4 C11 N1 -175.7(2) . . . . ?
C16 C1 C2 O1 -113.6(3) . . . . ?
C16 C1 C2 O2 64.2(3) . . . . ?
C16 C17 C18 C19 177.0(3) . . . . ?
C16 C17 C22 C21 -177.0(3) . . . . ?
C17 C18 C19 C20 -0.1(5) . . . . ?
C18 C17 C22 C21 2.2(4) . . . . ?
C18 C19 C20 N2 -175.8(3) . . . . ?
C18 C19 C20 C21 2.4(4) . . . . ?
C19 C20 C21 C22 -2.4(4) . . . . ?
C20 N2 C23 C24 -84.1(4) . . . . ?
C20 N2 C25 C26 -83.4(4) . . . . ?
C20 C21 C22 C17 0.1(5) . . . . ?
C22 C17 C18 C19 -2.2(4) . . . . ?
C23 N2 C20 C19 0.2(5) . . . . ?
C23 N2 C20 C21 -178.1(3) . . . . ?
C23 N2 C25 C26 100.8(4) . . . . ?
C25 N2 C20 C19 -175.4(3) . . . . ?
C25 N2 C20 C21 6.4(5) . . . . ?
C25 N2 C23 C24 91.6(4) . . . . ?

_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.917
_oxdiff_exptl_absorpt_empirical_full_min 0.661
####################################################################### 
# 
# 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_mf7_hklf5
_database_code_depnum_ccdc_archive 'CCDC 2335491'
loop_
_audit_author_name
_audit_author_address
'Farzaneh Fadaei Tirani'
;EPFL
Switzerland
;
_audit_update_record             
;
2024-02-26 deposited with the CCDC.	2024-05-21 downloaded from the CCDC.
;
_audit_creation_date             2018-12-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'

# start Validation Reply Form
_vrf_PLAT084_mf7_hklf5           
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.46 Report
RESPONSE: The quality of this crystal was poor, however, it represents the
          best possible data after multiple recrystallization attempts.
;
_vrf_PLAT029_mf7_hklf5           
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.958 Why?  
RESPONSE: This is due to TWO-component twin refinement
          and non-centrosymmetric structure.  
;
_vrf_PLAT082_mf7_hklf5           
;
PROBLEM: High R1 Value ..................................       0.18 Report
RESPONSE: The quality of this crystal was poor, however, it represents the
          best possible data after multiple recrystallization attempts.
;
_vrf_PLAT340_mf7_hklf5           
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02524 Ang.  
RESPONSE: The quality of this crystal was poor, however, it represents the
          best possible data after multiple recrystallization attempts.
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H22 Cl2 F17 N2 O2, Cl, C2 H3 N'
_chemical_formula_sum            'C25 H25 Cl3 F17 N3 O2'
_chemical_formula_weight         828.83
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C23 H22 N2 O2F17 Cl3'
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'
Cl Cl 0.3639 0.7018 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'I 1 2 1'
_space_group_name_Hall           'I 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'

_cell_length_a                   22.4357(14)
_cell_length_b                   5.2436(3)
_cell_length_c                   27.9895(18)
_cell_angle_alpha                90
_cell_angle_beta                 96.882(6)
_cell_angle_gamma                90
_cell_volume                     3269.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2123
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      73.0650
_cell_measurement_theta_min      4.8010
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.741
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.289
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018).
 Numerical absorption correction based on Gaussian integration over
 a multifaceted crystal model/Empirical absorption correction using
 spherical harmonics as implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.684
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1664
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 0 18 0.0148
4 0 -18 0.0148
-13 0 -6 0.0360
2 -3 0 0.3572
0 -3 0 0.3583
0 3 0 0.3583
-3 -2 16 0.1977
-14 -1 -3 0.1178
15 0 -1 0.0263

_exptl_crystal_size_max          0.717
_exptl_crystal_size_mid          0.069
_exptl_crystal_size_min          0.03
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-3.9620 -0.0287 17.9871 -0.4166 -0.9095 -0.0605
3.9620 0.0287 -17.9871 0.4166 0.9095 0.0605
-13.0469 0.0016 -5.9137 0.9649 -0.2464 -0.0247
2.0516 -2.9916 -0.1499 -0.1090 0.0165 0.8834
0.0468 -2.9927 -0.1384 0.0062 -0.0602 0.8771
-0.0468 2.9927 0.1384 -0.0062 0.0602 -0.8771
-2.9336 -2.0204 15.8930 -0.3982 -0.8273 0.5327
-14.0257 -1.0010 -2.9601 0.9168 -0.4308 0.2566
15.0332 0.0098 -1.0839 -0.8285 0.6171 0.0496

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0621
_diffrn_reflns_Laue_measured_fraction_full 0.958
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            5297
_diffrn_reflns_point_group_measured_fraction_full 0.744
_diffrn_reflns_point_group_measured_fraction_max 0.744
_diffrn_reflns_theta_full        65.070
_diffrn_reflns_theta_max         65.070
_diffrn_reflns_theta_min         4.946
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2665
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -10.00   1.00    7.50    --  -42.76 -77.00 120.00  106
  2  ω    -71.00  23.00   1.00    7.50    --  -42.76  57.00 -90.00   94
  3  ω   -124.00 -88.00   1.00    7.50    --  -42.76 -99.00 -90.00   36
  4  ω     36.00 117.00   1.00    7.50    --   42.76  37.00   0.00   81
  5  ω     39.00 105.00   1.00    7.50    --   42.76-145.00  78.00   66
  6  ω     89.00 133.00   1.00   50.00    --  109.26  61.00  60.00   44
  7  ω     82.00 137.00   1.00   50.00    --  109.26 -61.00  60.00   55
  8  ω     39.00 129.00   1.00   50.00    --  109.26 -77.00-150.00   90
  9  ω     78.00 108.00   1.00   50.00    --  109.26-126.00-113.00   30
 10  ω     37.00  64.00   1.00   50.00    --  109.26-126.00-113.00   27
 11  ω     80.00 108.00   1.00   50.00    --  109.26  61.00  30.00   28
 12  ω    135.00 176.00   1.00   50.00    --  109.26  61.00  30.00   41
 13  ω     45.00 131.00   1.00   50.00    --  109.26 -45.00-120.00   86
 14  ω     45.00 133.00   1.00   50.00    --  109.26 -45.00  30.00   88
 15  ω     34.00  62.00   1.00   50.00    --  109.26-111.00 -60.00   28
 16  ω     78.00 113.00   1.00   50.00    --  109.26-111.00-180.00   35
 17  ω     60.00 107.00   1.00   50.00    --  109.26-111.00  30.00   47
 18  ω     84.00 109.00   1.00   50.00    --  109.26-111.00 -60.00   25
 19  ω     27.00 108.00   1.00   50.00    --  109.26 -94.00  60.00   81
 20  ω     21.00 178.00   1.00   50.00    --  109.26   0.00  30.00  157
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0576980000
_diffrn_orient_matrix_UB_12      -0.0013221000
_diffrn_orient_matrix_UB_13      -0.0358729000
_diffrn_orient_matrix_UB_21      0.0379969000
_diffrn_orient_matrix_UB_22      0.0226519000
_diffrn_orient_matrix_UB_23      -0.0421608000
_diffrn_orient_matrix_UB_31      0.0032660000
_diffrn_orient_matrix_UB_32      -0.2928850000
_diffrn_orient_matrix_UB_33      -0.0031142000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.386
_reflns_Friedel_fraction_full    0.472
_reflns_Friedel_fraction_max     0.472
_reflns_number_gt                3614
_reflns_number_total             5297
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_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 (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         1.630
_refine_diff_density_min         -1.471
_refine_diff_density_rms         0.223
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.01(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.830
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     454
_refine_ls_number_reflns         5297
_refine_ls_number_restraints     562
_refine_ls_R_factor_all          0.2102
_refine_ls_R_factor_gt           0.1769
_refine_ls_restrained_S_all      1.803
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4322
_refine_ls_wR_factor_ref         0.4649
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.528(16)
 0.472(16)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 F2-C5 = F1-C5
 1.33 with sigma of 0.01
 F3-C6 = F4-C6
 1.33 with sigma of 0.01
 C4-C5 = C5-C6 = C7-C6 = C7-C8 = C9-C8 = C10-C9
 1.54 with sigma of 0.01
 F8-C8 = F7-C8
 1.33 with sigma of 0.01
 F11-C10 = F12-C10
 1.33 with sigma of 0.01
 F10-C9 = F9-C9 = F8-C8 = F7-C8 = F6-C7 = F5-C7 = F4-C6 = F3-C6 = F1-C5 = F2-C5
 1.33 with sigma of 0.01
 C11-C10 = C10-C9 = C9-C8 = C7-C8 = C7-C6 = C5-C6 = C4-C5
 1.54 with sigma of 0.01
 F14-C11 = F13-C11
 1.33 with sigma of 0.01
 C11-C12
 1.54 with sigma of 0.01
 F17-C12 = F16-C12 = F15-C12
 1.33 with sigma of 0.01
 F15-F16
 2.15 with sigma of 0.01
 F16-F17
 2.15 with sigma of 0.01
 F17-F15
 2.15 with sigma of 0.01
 C11-F16
 2.3 with sigma of 0.01
 F2-F1
 2.15 with sigma of 0.01
 F3-F4
 2.15 with sigma of 0.01
 F5-F6
 2.15 with sigma of 0.01
 F7-F8
 2.15 with sigma of 0.01
 F9-F10
 2.15 with sigma of 0.01
 F11-F12
 2.15 with sigma of 0.01
 F14-F13
 2.15 with sigma of 0.01
 F15-F17 \\sim F17-F16
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
F1 \\sim F2 \\sim F3 \\sim F4 \\sim F5 \\sim F6 \\sim F7 \\sim F8 \\sim F9
\\sim F10 \\sim F11 \\sim F12 \\sim F13 \\sim F14 \\sim F15 \\sim F16 \\sim F17
\\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9 \\sim C10 \\sim C11 \\sim C12:
within 2A with sigma of 0.001 and sigma for terminal atoms of 0.002
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6.a Ternary CH refined with riding coordinates:
 C1(H1)
6.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C13(H13A,H13B), C20(H20A,H20B), C21(H21A,H21B),
 C22(H22A,H22B), C23(H23A,H23B)
6.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C18(H18), C19(H19)
6.d Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
Cl1 Cl 0.1471(2) 0.1860(18) 0.4750(3) 0.081(2) Uani 1 1 d . U . . .
Cl2 Cl 0.4660(2) -0.1604(13) 0.57316(19) 0.0638(16) Uani 1 1 d . U . . .
F1 F 0.5718(7) 0.721(2) 0.3107(6) 0.080(2) Uani 1 1 d D U . . .
F2 F 0.5798(7) 0.343(3) 0.3409(5) 0.080(2) Uani 1 1 d D U . . .
F3 F 0.6651(7) 0.647(3) 0.2628(6) 0.081(2) Uani 1 1 d D U . . .
F4 F 0.6699(7) 0.252(2) 0.2843(6) 0.080(2) Uani 1 1 d D U . . .
F5 F 0.6781(7) 0.763(3) 0.3662(6) 0.085(2) Uani 1 1 d D U . . .
F6 F 0.6974(7) 0.365(3) 0.3759(6) 0.084(2) Uani 1 1 d D U . . .
F7 F 0.7658(8) 0.855(3) 0.3181(6) 0.088(2) Uani 1 1 d D U . . .
F8 F 0.7803(8) 0.459(3) 0.3032(6) 0.087(2) Uani 1 1 d D U . . .
F9 F 0.7894(8) 0.742(3) 0.4167(6) 0.093(2) Uani 1 1 d D U . . .
F10 F 0.8151(8) 0.369(3) 0.3964(7) 0.093(2) Uani 1 1 d D U . . .
F11 F 0.8749(9) 0.894(3) 0.3428(7) 0.100(2) Uani 1 1 d D U . . .
F12 F 0.8940(8) 0.494(3) 0.3443(7) 0.100(2) Uani 1 1 d D U . . .
F13 F 0.9092(9) 0.944(3) 0.4256(7) 0.106(2) Uani 1 1 d D U . . .
F14 F 0.9096(9) 0.579(4) 0.4582(7) 0.103(2) Uani 1 1 d D U . . .
F15 F 0.9958(9) 0.839(3) 0.3733(6) 0.105(2) Uani 1 1 d D U . . .
F16 F 1.0018(8) 0.459(3) 0.4021(7) 0.107(2) Uani 1 1 d D U . . .
F17 F 1.0220(8) 0.777(4) 0.4490(6) 0.107(2) Uani 1 1 d D U . . .
O1 O 0.3720(7) 0.279(3) 0.2603(5) 0.053(3) Uani 1 1 d . U . . .
O2 O 0.4567(7) 0.492(3) 0.2833(5) 0.052(3) Uani 1 1 d . U . . .
N1 N 0.3044(6) 0.666(3) 0.2866(5) 0.040(3) Uani 1 1 d . U . . .
H1A H 0.287705 0.768945 0.307605 0.047 Uiso 1 1 calc GR . . . .
H1B H 0.297020 0.500317 0.293297 0.047 Uiso 1 1 calc GR . . . .
H1C H 0.288131 0.702985 0.256013 0.047 Uiso 1 1 calc GR . . . .
N2 N 0.3250(6) 0.123(3) 0.4876(5) 0.041(3) Uani 1 1 d . U . . .
C1 C 0.3703(8) 0.710(3) 0.2913(6) 0.039(3) Uani 1 1 d . U . . .
H1 H 0.378460 0.847531 0.268162 0.047 Uiso 1 1 calc R . . . .
C2 C 0.3990(9) 0.466(3) 0.2763(6) 0.038(3) Uani 1 1 d . U . . .
C3 C 0.4915(13) 0.284(5) 0.2661(11) 0.072(6) Uani 1 1 d . U . . .
H3A H 0.469770 0.212568 0.236206 0.086 Uiso 1 1 calc R . . . .
H3B H 0.496301 0.146957 0.290529 0.086 Uiso 1 1 calc R . . . .
C4 C 0.5528(10) 0.376(4) 0.2562(7) 0.064(4) Uani 1 1 d D U . . .
H4A H 0.548093 0.511113 0.231240 0.077 Uiso 1 1 calc R . . . .
H4B H 0.575305 0.233166 0.243796 0.077 Uiso 1 1 calc R . . . .
C5 C 0.5883(8) 0.483(3) 0.3025(6) 0.0812(18) Uani 1 1 d D U . . .
C6 C 0.6562(8) 0.486(3) 0.2980(5) 0.0824(17) Uani 1 1 d D U . . .
C7 C 0.6975(8) 0.558(3) 0.3443(6) 0.0850(16) Uani 1 1 d D U . . .
C8 C 0.7628(8) 0.619(3) 0.3359(6) 0.0885(16) Uani 1 1 d D U . . .
C9 C 0.8097(8) 0.610(4) 0.3809(6) 0.0930(17) Uani 1 1 d D U . . .
C10 C 0.8736(9) 0.684(4) 0.3709(7) 0.0976(17) Uani 1 1 d D U . . .
C11 C 0.9189(8) 0.694(4) 0.4169(7) 0.1014(18) Uani 1 1 d D U . . .
C12 C 0.9858(8) 0.698(3) 0.4112(7) 0.1038(19) Uani 1 1 d D U . . .
C13 C 0.3925(7) 0.803(3) 0.3422(5) 0.033(3) Uani 1 1 d . U . . .
H13A H 0.436556 0.824625 0.345036 0.039 Uiso 1 1 calc R . . . .
H13B H 0.374564 0.971831 0.347116 0.039 Uiso 1 1 calc R . . . .
C14 C 0.3775(7) 0.625(3) 0.3819(5) 0.036(3) Uani 1 1 d . U . . .
C15 C 0.4153(8) 0.426(4) 0.3999(5) 0.035(3) Uani 1 1 d . U . . .
H15 H 0.452886 0.402338 0.388040 0.042 Uiso 1 1 calc R . . . .
C16 C 0.3986(7) 0.263(3) 0.4347(6) 0.034(3) Uani 1 1 d . U . . .
H16 H 0.425485 0.131899 0.446949 0.040 Uiso 1 1 calc R . . . .
C17 C 0.3429(7) 0.286(3) 0.4522(5) 0.034(3) Uani 1 1 d . U . . .
C18 C 0.3048(8) 0.487(3) 0.4346(5) 0.037(3) Uani 1 1 d . U . . .
H18 H 0.267247 0.510554 0.446487 0.044 Uiso 1 1 calc R . . . .
C19 C 0.3222(7) 0.652(4) 0.3997(5) 0.040(3) Uani 1 1 d . U . . .
H19 H 0.295886 0.785109 0.387783 0.048 Uiso 1 1 calc R . . . .
C20 C 0.2671(8) 0.156(4) 0.5028(6) 0.045(4) Uani 1 1 d . U . . .
H20A H 0.260434 0.339482 0.508732 0.054 Uiso 1 1 calc R . . . .
H20B H 0.265440 0.063856 0.533501 0.054 Uiso 1 1 calc R . . . .
C21 C 0.2171(9) 0.058(5) 0.4654(9) 0.057(5) Uani 1 1 d . U . . .
H21A H 0.215402 -0.130638 0.467125 0.068 Uiso 1 1 calc R . . . .
H21B H 0.226227 0.105036 0.432771 0.068 Uiso 1 1 calc R . . . .
C22 C 0.3663(8) -0.066(3) 0.5109(6) 0.039(4) Uani 1 1 d . U . . .
H22A H 0.388680 -0.147564 0.486559 0.047 Uiso 1 1 calc R . . . .
H22B H 0.343418 -0.199594 0.525650 0.047 Uiso 1 1 calc R . . . .
C23 C 0.4109(9) 0.061(4) 0.5499(7) 0.045(4) Uani 1 1 d . U . . .
H23A H 0.389095 0.124556 0.576168 0.054 Uiso 1 1 calc R . . . .
H23B H 0.430429 0.207757 0.535915 0.054 Uiso 1 1 calc R . . . .
Cl3 Cl 0.24245(18) 0.1590(10) 0.32340(13) 0.0404(11) Uani 1 1 d . U . . .
N3 N 0.9345(12) 0.268(5) 0.6805(8) 0.083(7) Uani 1 1 d . U . . .
C24 C 0.9047(11) 0.409(5) 0.6619(7) 0.058(5) Uani 1 1 d . U . . .
C25 C 0.8647(9) 0.603(4) 0.6400(9) 0.055(5) Uani 1 1 d . U . . .
H25A H 0.860187 0.737835 0.663463 0.083 Uiso 1 1 calc GR . . . .
H25B H 0.825388 0.526897 0.629452 0.083 Uiso 1 1 calc GR . . . .
H25C H 0.881383 0.674933 0.612154 0.083 Uiso 1 1 calc GR . . . .


_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
Cl1 C21 1.76(2) . ?
Cl2 C23 1.761(19) . ?
F1 C5 1.329(10) . ?
F2 C5 1.336(10) . ?
F3 C6 1.335(10) . ?
F4 C6 1.332(10) . ?
F5 C7 1.337(13) . ?
F6 C7 1.345(13) . ?
F7 C8 1.339(10) . ?
F8 C8 1.332(10) . ?
F9 C9 1.339(13) . ?
F10 C9 1.337(13) . ?
F11 C10 1.356(13) . ?
F12 C10 1.354(13) . ?
F13 C11 1.359(13) . ?
F14 C11 1.342(13) . ?
F15 C12 1.331(13) . ?
F16 C12 1.337(13) . ?
F17 C12 1.321(13) . ?
O1 C2 1.21(2) . ?
O2 C2 1.29(2) . ?
O2 C3 1.46(3) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N1 C1 1.49(2) . ?
N2 C17 1.40(2) . ?
N2 C20 1.43(2) . ?
N2 C22 1.45(2) . ?
C1 H1 1.0000 . ?
C1 C2 1.51(2) . ?
C1 C13 1.53(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.51(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.542(10) . ?
C5 C6 1.544(10) . ?
C6 C7 1.545(10) . ?
C7 C8 1.545(10) . ?
C8 C9 1.543(10) . ?
C9 C10 1.542(10) . ?
C10 C11 1.543(13) . ?
C11 C12 1.528(13) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.52(2) . ?
C14 C15 1.40(2) . ?
C14 C19 1.40(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.38(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.40(2) . ?
C17 C18 1.41(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.39(3) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.53(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.54(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
N3 C24 1.09(3) . ?
C24 C25 1.44(3) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?

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
C2 O2 C3 116.0(17) . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
C17 N2 C20 118.9(14) . . ?
C17 N2 C22 120.7(14) . . ?
C20 N2 C22 120.2(15) . . ?
N1 C1 H1 108.1 . . ?
N1 C1 C2 107.2(14) . . ?
N1 C1 C13 109.9(14) . . ?
C2 C1 H1 108.1 . . ?
C2 C1 C13 115.1(14) . . ?
C13 C1 H1 108.1 . . ?
O1 C2 O2 126.1(18) . . ?
O1 C2 C1 125.2(18) . . ?
O2 C2 C1 108.7(15) . . ?
O2 C3 H3A 109.5 . . ?
O2 C3 H3B 109.5 . . ?
O2 C3 C4 111(2) . . ?
H3A C3 H3B 108.1 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 C5 110.5(18) . . ?
H4A C4 H4B 108.1 . . ?
C5 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
F1 C5 F2 107.9(11) . . ?
F1 C5 C4 111.0(16) . . ?
F1 C5 C6 107.6(14) . . ?
F2 C5 C4 111.6(15) . . ?
F2 C5 C6 107.9(13) . . ?
C4 C5 C6 110.6(14) . . ?
F3 C6 C5 107.6(13) . . ?
F3 C6 C7 109.6(15) . . ?
F4 C6 F3 108.2(11) . . ?
F4 C6 C5 106.1(13) . . ?
F4 C6 C7 109.4(15) . . ?
C5 C6 C7 115.7(13) . . ?
F5 C7 F6 106.1(12) . . ?
F5 C7 C6 112.7(15) . . ?
F5 C7 C8 105.6(14) . . ?
F6 C7 C6 108.6(15) . . ?
F6 C7 C8 109.3(14) . . ?
C6 C7 C8 114.1(14) . . ?
F7 C8 C7 109.8(15) . . ?
F7 C8 C9 105.7(16) . . ?
F8 C8 F7 107.0(11) . . ?
F8 C8 C7 109.7(15) . . ?
F8 C8 C9 108.4(16) . . ?
C9 C8 C7 115.9(13) . . ?
F9 C9 C8 109.6(16) . . ?
F9 C9 C10 114.4(16) . . ?
F10 C9 F9 105.8(12) . . ?
F10 C9 C8 108.6(17) . . ?
F10 C9 C10 104.2(16) . . ?
C10 C9 C8 113.7(14) . . ?
F11 C10 C9 113.2(17) . . ?
F11 C10 C11 113.5(18) . . ?
F12 C10 F11 104.2(12) . . ?
F12 C10 C9 107.5(16) . . ?
F12 C10 C11 104.6(17) . . ?
C9 C10 C11 113.0(15) . . ?
F13 C11 C10 94.5(16) . . ?
F13 C11 C12 100.6(18) . . ?
F14 C11 F13 103.5(12) . . ?
F14 C11 C10 123.3(18) . . ?
F14 C11 C12 110.8(16) . . ?
C12 C11 C10 118.0(14) . . ?
F15 C12 F16 107.0(13) . . ?
F15 C12 C11 110.8(16) . . ?
F16 C12 C11 107.1(11) . . ?
F17 C12 F15 108.5(12) . . ?
F17 C12 F16 107.0(12) . . ?
F17 C12 C11 115.9(17) . . ?
C1 C13 H13A 108.7 . . ?
C1 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C14 C13 C1 114.4(13) . . ?
C14 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
C15 C14 C13 123.0(16) . . ?
C19 C14 C13 118.9(15) . . ?
C19 C14 C15 118.0(16) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.8(16) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 119.3 . . ?
C15 C16 C17 121.5(15) . . ?
C17 C16 H16 119.3 . . ?
N2 C17 C16 122.4(14) . . ?
N2 C17 C18 119.4(14) . . ?
C16 C17 C18 118.1(16) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.0(16) . . ?
C19 C18 H18 120.0 . . ?
C14 C19 H19 119.2 . . ?
C18 C19 C14 121.6(16) . . ?
C18 C19 H19 119.2 . . ?
N2 C20 H20A 109.2 . . ?
N2 C20 H20B 109.2 . . ?
N2 C20 C21 111.9(16) . . ?
H20A C20 H20B 107.9 . . ?
C21 C20 H20A 109.2 . . ?
C21 C20 H20B 109.2 . . ?
Cl1 C21 H21A 109.4 . . ?
Cl1 C21 H21B 109.4 . . ?
C20 C21 Cl1 111.1(16) . . ?
C20 C21 H21A 109.4 . . ?
C20 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
N2 C22 H22A 109.5 . . ?
N2 C22 H22B 109.5 . . ?
N2 C22 C23 110.5(15) . . ?
H22A C22 H22B 108.1 . . ?
C23 C22 H22A 109.5 . . ?
C23 C22 H22B 109.5 . . ?
Cl2 C23 H23A 109.6 . . ?
Cl2 C23 H23B 109.6 . . ?
C22 C23 Cl2 110.3(14) . . ?
C22 C23 H23A 109.6 . . ?
C22 C23 H23B 109.6 . . ?
H23A C23 H23B 108.1 . . ?
N3 C24 C25 177(3) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A Cl3 0.91 2.35 3.164(16) 149.0 1_565 yes
N1 H1B Cl3 0.91 2.38 3.227(15) 155.1 . yes
N1 H1C Cl3 0.91 2.26 3.132(12) 160.9 4 yes

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
F1 C5 C6 F3 -57.3(16) . . . . ?
F1 C5 C6 F4 -172.9(14) . . . . ?
F1 C5 C6 C7 65.6(16) . . . . ?
F2 C5 C6 F3 -173.5(14) . . . . ?
F2 C5 C6 F4 70.9(16) . . . . ?
F2 C5 C6 C7 -50.6(17) . . . . ?
F3 C6 C7 F5 75.6(17) . . . . ?
F3 C6 C7 F6 -167.1(13) . . . . ?
F3 C6 C7 C8 -44.9(18) . . . . ?
F4 C6 C7 F5 -166.0(13) . . . . ?
F4 C6 C7 F6 -48.7(17) . . . . ?
F4 C6 C7 C8 73.5(17) . . . . ?
F5 C7 C8 F7 -45.9(18) . . . . ?
F5 C7 C8 F8 -163.2(15) . . . . ?
F5 C7 C8 C9 73.8(18) . . . . ?
F6 C7 C8 F7 -159.7(15) . . . . ?
F6 C7 C8 F8 83.1(17) . . . . ?
F6 C7 C8 C9 -40.0(19) . . . . ?
F7 C8 C9 F9 73.8(16) . . . . ?
F7 C8 C9 F10 -171.1(14) . . . . ?
F7 C8 C9 C10 -55.6(18) . . . . ?
F8 C8 C9 F9 -171.8(14) . . . . ?
F8 C8 C9 F10 -56.7(17) . . . . ?
F8 C8 C9 C10 58.8(19) . . . . ?
F9 C9 C10 F11 -82(2) . . . . ?
F9 C9 C10 F12 163.5(16) . . . . ?
F9 C9 C10 C11 49(2) . . . . ?
F10 C9 C10 F11 162.9(17) . . . . ?
F10 C9 C10 F12 48.5(19) . . . . ?
F10 C9 C10 C11 -66(2) . . . . ?
F11 C10 C11 F13 40.2(18) . . . . ?
F11 C10 C11 F14 149.6(17) . . . . ?
F11 C10 C11 C12 -64(2) . . . . ?
F12 C10 C11 F13 153.0(15) . . . . ?
F12 C10 C11 F14 -97.6(18) . . . . ?
F12 C10 C11 C12 49(2) . . . . ?
F13 C11 C12 F15 -63.4(18) . . . . ?
F13 C11 C12 F16 -179.8(15) . . . . ?
F13 C11 C12 F17 60.8(19) . . . . ?
F14 C11 C12 F15 -172.4(16) . . . . ?
F14 C11 C12 F16 71.2(19) . . . . ?
F14 C11 C12 F17 -48(2) . . . . ?
O2 C3 C4 C5 61(3) . . . . ?
N1 C1 C2 O1 5(2) . . . . ?
N1 C1 C2 O2 -175.4(13) . . . . ?
N1 C1 C13 C14 56.4(18) . . . . ?
N2 C17 C18 C19 179.6(15) . . . . ?
N2 C20 C21 Cl1 -161.5(15) . . . . ?
N2 C22 C23 Cl2 -173.3(12) . . . . ?
C1 C13 C14 C15 89.2(19) . . . . ?
C1 C13 C14 C19 -87.2(19) . . . . ?
C2 O2 C3 C4 155.5(18) . . . . ?
C2 C1 C13 C14 -65(2) . . . . ?
C3 O2 C2 O1 6(3) . . . . ?
C3 O2 C2 C1 -173.9(18) . . . . ?
C3 C4 C5 F1 -81(2) . . . . ?
C3 C4 C5 F2 39(2) . . . . ?
C3 C4 C5 C6 159.5(17) . . . . ?
C4 C5 C6 F3 64.1(17) . . . . ?
C4 C5 C6 F4 -51.4(17) . . . . ?
C4 C5 C6 C7 -173.0(14) . . . . ?
C5 C6 C7 F5 -46.2(18) . . . . ?
C5 C6 C7 F6 71.1(17) . . . . ?
C5 C6 C7 C8 -166.7(13) . . . . ?
C6 C7 C8 F7 78.5(17) . . . . ?
C6 C7 C8 F8 -38.8(19) . . . . ?
C6 C7 C8 C9 -161.8(14) . . . . ?
C7 C8 C9 F9 -48(2) . . . . ?
C7 C8 C9 F10 67.1(18) . . . . ?
C7 C8 C9 C10 -177.5(15) . . . . ?
C8 C9 C10 F11 45(2) . . . . ?
C8 C9 C10 F12 -69(2) . . . . ?
C8 C9 C10 C11 175.7(15) . . . . ?
C9 C10 C11 F13 -90.4(19) . . . . ?
C9 C10 C11 F14 19(2) . . . . ?
C9 C10 C11 C12 165.1(16) . . . . ?
C10 C11 C12 F15 37(2) . . . . ?
C10 C11 C12 F16 -79(2) . . . . ?
C10 C11 C12 F17 161.7(17) . . . . ?
C13 C1 C2 O1 127.2(19) . . . . ?
C13 C1 C2 O2 -53(2) . . . . ?
C13 C14 C15 C16 -177.3(14) . . . . ?
C13 C14 C19 C18 177.0(14) . . . . ?
C14 C15 C16 C17 2(2) . . . . ?
C15 C14 C19 C18 0(2) . . . . ?
C15 C16 C17 N2 -180.0(15) . . . . ?
C15 C16 C17 C18 -2(2) . . . . ?
C16 C17 C18 C19 2(2) . . . . ?
C17 N2 C20 C21 75(2) . . . . ?
C17 N2 C22 C23 79(2) . . . . ?
C17 C18 C19 C14 -1(2) . . . . ?
C19 C14 C15 C16 -1(2) . . . . ?
C20 N2 C17 C16 -178.7(16) . . . . ?
C20 N2 C17 C18 3(2) . . . . ?
C20 N2 C22 C23 -97(2) . . . . ?
C22 N2 C17 C16 6(2) . . . . ?
C22 N2 C17 C18 -172.1(15) . . . . ?
C22 N2 C20 C21 -109.4(19) . . . . ?

_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 4.861
_oxdiff_exptl_absorpt_empirical_full_min 0.292
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.528(16) 2864 7952 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.472(16) 0 7952 nmt 0.9999 -0.0467 0.0155 0.0020 1.0008 -0.0050 -0.0205
0.1476 0.9987

_twin_special_details            
;
Component 2 rotated by 1.8999° 
 around [0.92 0.13 0.36] (reciprocal) or [0.36 0.92 0.12] (direct)
;
####################################################################### 
# 
# 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_sz01
_database_code_depnum_ccdc_archive 'CCDC 2335489'
loop_
_audit_author_name
_audit_author_address
'Farzaneh Fadaei Tirani'
;EPFL
Switzerland
;
_audit_update_record             
;
2024-02-26 deposited with the CCDC.	2024-05-21 downloaded from the CCDC.
;
_audit_creation_date             2018-12-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H29 Cl2 F17 N2 O4'
_chemical_formula_sum            'C28 H29 Cl2 F17 N2 O4'
_chemical_formula_weight         851.43
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C28 H29 N2 O4 F17 Cl2'
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'
Cl Cl 0.3639 0.7018 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   11.0351(3)
_cell_length_b                   32.0681(9)
_cell_length_c                   9.7587(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3453.38(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7854
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      74.7110
_cell_measurement_theta_min      4.1040
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.901
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.454
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2018).
 Numerical absorption correction based on Gaussian integration over
 a multifaceted crystal model/Empirical absorption correction using
 spherical harmonics as implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1720
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 21 0 0.0107
-1 -21 0 0.0197
2 -1 -6 0.1607
-2 1 6 0.2837
-7 4 0 0.0576
7 -4 0 0.0766

_exptl_crystal_size_max          0.504
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.03
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0000 20.9995 -0.0000 0.8004 0.6241 -0.0841
-1.0000 -20.9995 0.0000 -0.8004 -0.6241 0.0841
2.0000 -1.0006 -6.0000 -0.1644 0.3190 0.9208
-2.0000 1.0006 6.0000 0.1644 -0.3190 -0.9208
-7.0000 4.0016 0.0000 0.6587 -0.7441 0.0694
7.0000 -4.0016 -0.0000 -0.6587 0.7441 -0.0694

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            23896
_diffrn_reflns_point_group_measured_fraction_full 0.793
_diffrn_reflns_point_group_measured_fraction_max 0.763
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.428
_diffrn_reflns_theta_min         4.136
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2665
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -71.00  27.00   1.00   25.00    --  -43.01  57.00 -30.00   98
  2  ω    -67.00  30.00   1.00   25.00    --  -43.01  37.00-150.00   97
  3  ω   -116.00 -19.00   1.00   25.00    --  -43.01 -37.00  30.00   97
  4  ω     21.00  68.00   1.00   25.00    --   43.01 -99.00  60.00   47
  5  ω     43.00  78.00   1.00   25.00    --   43.01-125.00-120.00   35
  6  ω    110.00 160.00   1.00  100.00    --  109.26  30.00   0.00   50
  7  ω    107.00 133.00   1.00  100.00    --  109.26 -61.00   0.00   26
  8  ω    105.00 131.00   1.00  100.00    --  109.26 -77.00 150.00   26
  9  ω     42.00 132.00   1.00  100.00    --  109.26 -45.00 -30.00   90
 10  ω     29.00 102.00   1.00  100.00    --  109.26 -94.00 150.00   73
 11  ω     36.00 135.00   1.00  100.00    --  109.26 -45.00 120.00   99
 12  ω     51.00 127.00   1.00  100.00    --  109.26 -45.00-150.00   76
 13  ω     65.00 105.00   1.00  100.00    --  109.26 -94.00  60.00   40
 14  ω     82.00 109.00   1.00  100.00    --  109.26 -94.00-180.00   27
 15  ω     63.00 107.00   1.00  100.00    --  109.26-111.00 -30.00   44
 16  ω     33.00  99.00   1.00  100.00    --  109.26-111.00  30.00   66
 17  ω     24.00 170.00   1.00  100.00    --  109.26   0.00 -30.00  146
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0703983000
_diffrn_orient_matrix_UB_12      0.0414681000
_diffrn_orient_matrix_UB_13      -0.0029801000
_diffrn_orient_matrix_UB_21      0.1200291000
_diffrn_orient_matrix_UB_22      0.0240055000
_diffrn_orient_matrix_UB_23      -0.0171555000
_diffrn_orient_matrix_UB_31      -0.0118845000
_diffrn_orient_matrix_UB_32      -0.0034379000
_diffrn_orient_matrix_UB_33      -0.1568512000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.454
_reflns_Friedel_fraction_full    0.557
_reflns_Friedel_fraction_max     0.509
_reflns_number_gt                5000
_reflns_number_total             5468
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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         0.543
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 
;
 Flack x determined using 1413 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     485
_refine_ls_number_reflns         5468
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0391
_refine_ls_restrained_S_all      1.041
_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)+(0.0585P)²+0.9413P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1062
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl2-C28
 1.78 with sigma of 0.01
 C26-C25 \\sim C28-C27
 with sigma of 0.02
 N2-C25 \\sim N2-C27
 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C1(H1A)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C18(H18A,H18B), C25(H25A,H25B), C26(H26A,H26B),
 C27(H27A,H27B), C28(H28A,H28B)
3.c Aromatic/amide H refined with riding coordinates:
 C20(H20), C21(H21), C23(H23), C24(H24)
3.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
Cl1 Cl 0.35537(17) 0.07604(5) 0.9806(2) 0.0880(6) Uani 1 1 d . . . . .
Cl2 Cl 0.2853(2) 0.28979(4) 0.9614(2) 0.1106(9) Uani 1 1 d D . . . .
F1 F 0.5844(2) 0.31112(7) 0.1956(3) 0.0455(6) Uani 1 1 d . . . . .
F2 F 0.5971(2) 0.34495(7) 0.3883(3) 0.0454(6) Uani 1 1 d . . . . .
F3 F 0.6797(2) 0.38410(7) 0.0675(2) 0.0398(5) Uani 1 1 d . . . . .
F4 F 0.4947(2) 0.38046(8) 0.1437(3) 0.0535(8) Uani 1 1 d . . . . .
F5 F 0.5364(3) 0.42810(8) 0.3488(3) 0.0551(8) Uani 1 1 d . . . . .
F6 F 0.7328(3) 0.42273(7) 0.3311(3) 0.0428(6) Uani 1 1 d . . . . .
F7 F 0.7421(2) 0.46604(6) 0.1114(2) 0.0373(5) Uani 1 1 d . . . . .
F8 F 0.5493(2) 0.45909(7) 0.0679(2) 0.0405(5) Uani 1 1 d . . . . .
F9 F 0.4857(2) 0.50753(7) 0.2671(3) 0.0433(6) Uani 1 1 d . . . . .
F10 F 0.6626(3) 0.50445(7) 0.3653(2) 0.0451(6) Uani 1 1 d . . . . .
F11 F 0.76633(19) 0.54870(7) 0.1801(3) 0.0455(6) Uani 1 1 d . . . . .
F12 F 0.6236(2) 0.53839(7) 0.0310(2) 0.0412(6) Uani 1 1 d . . . . .
F13 F 0.46936(19) 0.58473(7) 0.1646(3) 0.0479(6) Uani 1 1 d . . . . .
F14 F 0.5840(3) 0.58729(8) 0.3465(3) 0.0515(7) Uani 1 1 d . . . . .
F15 F 0.7473(2) 0.63235(8) 0.2113(4) 0.0638(9) Uani 1 1 d . . . . .
F16 F 0.5706(2) 0.65745(7) 0.1795(3) 0.0536(7) Uani 1 1 d . . . . .
F17 F 0.6569(3) 0.62222(9) 0.0195(4) 0.0665(9) Uani 1 1 d . . . . .
O1 O 0.8414(2) 0.21390(7) 0.4208(3) 0.0286(5) Uani 1 1 d . . . . .
O2 O 0.7666(2) 0.25785(7) 0.2625(3) 0.0281(5) Uani 1 1 d . . . . .
O3 O 0.7267(2) 0.11713(7) 0.0652(3) 0.0292(5) Uani 1 1 d . . . . .
O4 O 0.8133(2) 0.08000(7) 0.2385(2) 0.0260(5) Uani 1 1 d . . . . .
N1 N 0.7661(3) 0.14617(8) 0.2722(3) 0.0226(5) Uani 1 1 d . . . . .
H1 H 0.776(4) 0.1410(12) 0.349(5) 0.022(10) Uiso 1 1 d . . . . .
N2 N 0.3762(3) 0.18392(10) 0.7729(4) 0.0396(8) Uani 1 1 d D . . . .
C1 C 0.7260(3) 0.18699(10) 0.2293(4) 0.0228(6) Uani 1 1 d . . . . .
H1A H 0.752413 0.191245 0.132326 0.027 Uiso 1 1 calc R . . . .
C2 C 0.7863(3) 0.21966(10) 0.3160(3) 0.0227(6) Uani 1 1 d . . . . .
C3 C 0.8072(3) 0.29254(10) 0.3456(4) 0.0306(8) Uani 1 1 d . . . . .
H3A H 0.895407 0.290429 0.362520 0.037 Uiso 1 1 calc R . . . .
H3B H 0.764851 0.292401 0.435103 0.037 Uiso 1 1 calc R . . . .
C4 C 0.7785(3) 0.33240(10) 0.2681(4) 0.0298(7) Uani 1 1 d . . . . .
H4A H 0.820591 0.355942 0.313375 0.036 Uiso 1 1 calc R . . . .
H4B H 0.811032 0.330014 0.173893 0.036 Uiso 1 1 calc R . . . .
C5 C 0.6453(3) 0.34217(11) 0.2602(4) 0.0303(7) Uani 1 1 d . . . . .
C6 C 0.6108(3) 0.38279(11) 0.1819(4) 0.0291(7) Uani 1 1 d . . . . .
C7 C 0.6290(3) 0.42431(10) 0.2607(4) 0.0286(7) Uani 1 1 d . . . . .
C8 C 0.6315(3) 0.46355(10) 0.1681(4) 0.0251(7) Uani 1 1 d . . . . .
C9 C 0.6054(3) 0.50492(11) 0.2445(4) 0.0281(7) Uani 1 1 d . . . . .
C10 C 0.6465(3) 0.54432(11) 0.1641(4) 0.0267(7) Uani 1 1 d . . . . .
C11 C 0.5843(3) 0.58522(11) 0.2103(4) 0.0318(8) Uani 1 1 d . . . . .
C12 C 0.6429(4) 0.62510(12) 0.1546(5) 0.0413(9) Uani 1 1 d . . . . .
C13 C 0.7643(3) 0.11433(10) 0.1817(3) 0.0214(6) Uani 1 1 d . . . . .
C14 C 0.8139(3) 0.04008(10) 0.1630(4) 0.0281(7) Uani 1 1 d . . . . .
C15 C 0.8895(4) 0.04400(12) 0.0339(4) 0.0333(8) Uani 1 1 d . . . . .
H15A H 0.849340 0.063009 -0.030291 0.050 Uiso 1 1 calc GR . . . .
H15B H 0.898394 0.016504 -0.008800 0.050 Uiso 1 1 calc GR . . . .
H15C H 0.969750 0.055019 0.057254 0.050 Uiso 1 1 calc GR . . . .
C16 C 0.8743(4) 0.01055(11) 0.2643(4) 0.0380(9) Uani 1 1 d . . . . .
H16A H 0.953381 0.021809 0.290996 0.057 Uiso 1 1 calc GR . . . .
H16B H 0.885300 -0.016808 0.221265 0.057 Uiso 1 1 calc GR . . . .
H16C H 0.823034 0.007625 0.345719 0.057 Uiso 1 1 calc GR . . . .
C17 C 0.6846(4) 0.02653(12) 0.1341(4) 0.0361(8) Uani 1 1 d . . . . .
H17A H 0.637206 0.027798 0.218944 0.054 Uiso 1 1 calc GR . . . .
H17B H 0.684620 -0.002109 0.099112 0.054 Uiso 1 1 calc GR . . . .
H17C H 0.648617 0.045153 0.065734 0.054 Uiso 1 1 calc GR . . . .
C18 C 0.5868(3) 0.19236(11) 0.2350(4) 0.0262(7) Uani 1 1 d . . . . .
H18A H 0.565282 0.219755 0.194984 0.031 Uiso 1 1 calc R . . . .
H18B H 0.548692 0.170509 0.177688 0.031 Uiso 1 1 calc R . . . .
C19 C 0.5351(3) 0.18976(11) 0.3782(4) 0.0242(7) Uani 1 1 d . . . . .
C20 C 0.5221(3) 0.22522(11) 0.4595(4) 0.0289(7) Uani 1 1 d . . . . .
H20 H 0.547821 0.251397 0.424380 0.035 Uiso 1 1 calc R . . . .
C21 C 0.4724(3) 0.22344(11) 0.5905(4) 0.0281(7) Uani 1 1 d . . . . .
H21 H 0.466251 0.248204 0.643463 0.034 Uiso 1 1 calc R . . . .
C22 C 0.4313(3) 0.18558(11) 0.6452(4) 0.0269(7) Uani 1 1 d . . . . .
C23 C 0.4478(3) 0.14980(11) 0.5654(4) 0.0293(7) Uani 1 1 d . . . . .
H23 H 0.424429 0.123405 0.600849 0.035 Uiso 1 1 calc R . . . .
C24 C 0.4980(3) 0.15230(11) 0.4347(4) 0.0277(7) Uani 1 1 d . . . . .
H24 H 0.507084 0.127468 0.382658 0.033 Uiso 1 1 calc R . . . .
C25 C 0.3281(4) 0.14527(13) 0.8275(5) 0.0398(9) Uani 1 1 d D . . . .
H25A H 0.293570 0.128529 0.751722 0.048 Uiso 1 1 calc R . . . .
H25B H 0.261864 0.151637 0.892691 0.048 Uiso 1 1 calc R . . . .
C26 C 0.4248(4) 0.12005(13) 0.9000(5) 0.0465(10) Uani 1 1 d D . . . .
H26A H 0.465771 0.137523 0.969587 0.056 Uiso 1 1 calc R . . . .
H26B H 0.486295 0.110523 0.833073 0.056 Uiso 1 1 calc R . . . .
C27 C 0.3783(5) 0.21934(14) 0.8653(5) 0.0489(11) Uani 1 1 d D . . . .
H27A H 0.453692 0.235477 0.850842 0.059 Uiso 1 1 calc R . . . .
H27B H 0.377686 0.209329 0.961301 0.059 Uiso 1 1 calc R . . . .
C28 C 0.2714(5) 0.24679(17) 0.8415(7) 0.0686(16) Uani 1 1 d D . . . .
H28A H 0.195269 0.231259 0.857866 0.082 Uiso 1 1 calc R . . . .
H28B H 0.271170 0.257248 0.746039 0.082 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
Cl1 C26 1.789(4) . ?
Cl2 C28 1.815(6) . ?
F1 C5 1.356(4) . ?
F2 C5 1.362(5) . ?
F3 C6 1.351(5) . ?
F4 C6 1.336(4) . ?
F5 C7 1.341(4) . ?
F6 C7 1.338(5) . ?
F7 C8 1.343(4) . ?
F8 C8 1.341(4) . ?
F9 C9 1.342(4) . ?
F10 C9 1.337(4) . ?
F11 C10 1.339(4) . ?
F12 C10 1.338(5) . ?
F13 C11 1.345(5) . ?
F14 C11 1.331(5) . ?
F15 C12 1.300(5) . ?
F16 C12 1.331(5) . ?
F17 C12 1.330(6) . ?
O1 C2 1.204(4) . ?
O2 C2 1.349(4) . ?
O2 C3 1.448(4) . ?
O3 C13 1.214(4) . ?
O4 C13 1.346(4) . ?
O4 C14 1.477(4) . ?
N1 H1 0.77(5) . ?
N1 C1 1.444(4) . ?
N1 C13 1.350(4) . ?
N2 C22 1.388(5) . ?
N2 C25 1.450(5) . ?
N2 C27 1.451(6) . ?
C1 H1A 1.0000 . ?
C1 C2 1.502(5) . ?
C1 C18 1.546(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.519(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.505(5) . ?
C5 C6 1.558(5) . ?
C6 C7 1.550(5) . ?
C7 C8 1.549(4) . ?
C8 C9 1.549(5) . ?
C9 C10 1.555(5) . ?
C10 C11 1.548(5) . ?
C11 C12 1.533(5) . ?
C14 C15 1.517(5) . ?
C14 C16 1.522(5) . ?
C14 C17 1.518(5) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.512(5) . ?
C19 C20 1.394(5) . ?
C19 C24 1.384(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.392(5) . ?
C21 H21 0.9500 . ?
C21 C22 1.402(5) . ?
C22 C23 1.399(5) . ?
C23 H23 0.9500 . ?
C23 C24 1.393(5) . ?
C24 H24 0.9500 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.514(6) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.490(7) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?

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
C2 O2 C3 115.5(3) . . ?
C13 O4 C14 120.4(3) . . ?
C1 N1 H1 121(3) . . ?
C13 N1 H1 118(3) . . ?
C13 N1 C1 119.5(3) . . ?
C22 N2 C25 121.5(3) . . ?
C22 N2 C27 121.4(3) . . ?
C25 N2 C27 116.6(4) . . ?
N1 C1 H1A 108.0 . . ?
N1 C1 C2 109.5(3) . . ?
N1 C1 C18 113.3(3) . . ?
C2 C1 H1A 108.0 . . ?
C2 C1 C18 110.1(3) . . ?
C18 C1 H1A 108.0 . . ?
O1 C2 O2 123.3(3) . . ?
O1 C2 C1 126.5(3) . . ?
O2 C2 C1 110.1(3) . . ?
O2 C3 H3A 110.2 . . ?
O2 C3 H3B 110.2 . . ?
O2 C3 C4 107.7(3) . . ?
H3A C3 H3B 108.5 . . ?
C4 C3 H3A 110.2 . . ?
C4 C3 H3B 110.2 . . ?
C3 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C5 C4 C3 113.8(3) . . ?
C5 C4 H4A 108.8 . . ?
C5 C4 H4B 108.8 . . ?
F1 C5 F2 106.3(3) . . ?
F1 C5 C4 110.8(3) . . ?
F1 C5 C6 105.3(3) . . ?
F2 C5 C4 110.4(3) . . ?
F2 C5 C6 107.5(3) . . ?
C4 C5 C6 116.0(3) . . ?
F3 C6 C5 107.1(3) . . ?
F3 C6 C7 108.1(3) . . ?
F4 C6 F3 108.1(3) . . ?
F4 C6 C5 108.9(3) . . ?
F4 C6 C7 108.1(3) . . ?
C7 C6 C5 116.3(3) . . ?
F5 C7 C6 107.3(3) . . ?
F5 C7 C8 108.3(3) . . ?
F6 C7 F5 109.0(3) . . ?
F6 C7 C6 109.5(3) . . ?
F6 C7 C8 108.4(3) . . ?
C8 C7 C6 114.2(3) . . ?
F7 C8 C7 107.7(3) . . ?
F7 C8 C9 108.4(3) . . ?
F8 C8 F7 108.7(3) . . ?
F8 C8 C7 109.0(3) . . ?
F8 C8 C9 108.5(3) . . ?
C9 C8 C7 114.3(3) . . ?
F9 C9 C8 108.4(3) . . ?
F9 C9 C10 108.6(3) . . ?
F10 C9 F9 108.7(3) . . ?
F10 C9 C8 109.1(3) . . ?
F10 C9 C10 108.4(3) . . ?
C8 C9 C10 113.5(3) . . ?
F11 C10 C9 108.3(3) . . ?
F11 C10 C11 108.4(3) . . ?
F12 C10 F11 108.3(3) . . ?
F12 C10 C9 108.6(3) . . ?
F12 C10 C11 108.6(3) . . ?
C11 C10 C9 114.4(3) . . ?
F13 C11 C10 108.2(3) . . ?
F13 C11 C12 106.9(3) . . ?
F14 C11 F13 109.3(3) . . ?
F14 C11 C10 109.5(3) . . ?
F14 C11 C12 108.3(4) . . ?
C12 C11 C10 114.6(3) . . ?
F15 C12 F16 108.3(4) . . ?
F15 C12 F17 109.4(4) . . ?
F15 C12 C11 111.8(4) . . ?
F16 C12 C11 109.4(3) . . ?
F17 C12 F16 107.8(4) . . ?
F17 C12 C11 110.0(4) . . ?
O3 C13 O4 125.7(3) . . ?
O3 C13 N1 124.1(3) . . ?
O4 C13 N1 110.1(3) . . ?
O4 C14 C15 110.2(3) . . ?
O4 C14 C16 102.6(3) . . ?
O4 C14 C17 109.7(3) . . ?
C15 C14 C16 110.5(3) . . ?
C15 C14 C17 112.7(3) . . ?
C17 C14 C16 110.7(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C1 C18 H18A 108.8 . . ?
C1 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?
C19 C18 C1 113.6(3) . . ?
C19 C18 H18A 108.8 . . ?
C19 C18 H18B 108.8 . . ?
C20 C19 C18 121.3(3) . . ?
C24 C19 C18 121.9(3) . . ?
C24 C19 C20 116.8(3) . . ?
C19 C20 H20 119.0 . . ?
C21 C20 C19 122.0(3) . . ?
C21 C20 H20 119.0 . . ?
C20 C21 H21 119.6 . . ?
C20 C21 C22 120.9(3) . . ?
C22 C21 H21 119.6 . . ?
N2 C22 C21 121.1(3) . . ?
N2 C22 C23 121.7(3) . . ?
C23 C22 C21 117.1(3) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 C22 121.0(3) . . ?
C24 C23 H23 119.5 . . ?
C19 C24 C23 122.2(3) . . ?
C19 C24 H24 118.9 . . ?
C23 C24 H24 118.9 . . ?
N2 C25 H25A 109.3 . . ?
N2 C25 H25B 109.3 . . ?
N2 C25 C26 111.7(4) . . ?
H25A C25 H25B 107.9 . . ?
C26 C25 H25A 109.3 . . ?
C26 C25 H25B 109.3 . . ?
Cl1 C26 H26A 109.9 . . ?
Cl1 C26 H26B 109.9 . . ?
C25 C26 Cl1 109.0(3) . . ?
C25 C26 H26A 109.9 . . ?
C25 C26 H26B 109.9 . . ?
H26A C26 H26B 108.3 . . ?
N2 C27 H27A 109.5 . . ?
N2 C27 H27B 109.5 . . ?
N2 C27 C28 110.7(5) . . ?
H27A C27 H27B 108.1 . . ?
C28 C27 H27A 109.5 . . ?
C28 C27 H27B 109.5 . . ?
Cl2 C28 H28A 110.5 . . ?
Cl2 C28 H28B 110.5 . . ?
C27 C28 Cl2 106.3(4) . . ?
C27 C28 H28A 110.5 . . ?
C27 C28 H28B 110.5 . . ?
H28A C28 H28B 108.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O3 0.77(5) 2.25(5) 3.009(4) 168(4) 4_655 yes

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
F1 C5 C6 F3 -80.0(3) . . . . ?
F1 C5 C6 F4 36.7(4) . . . . ?
F1 C5 C6 C7 159.1(3) . . . . ?
F2 C5 C6 F3 166.9(3) . . . . ?
F2 C5 C6 F4 -76.4(4) . . . . ?
F2 C5 C6 C7 46.0(4) . . . . ?
F3 C6 C7 F5 162.1(3) . . . . ?
F3 C6 C7 F6 -79.8(4) . . . . ?
F3 C6 C7 C8 42.0(4) . . . . ?
F4 C6 C7 F5 45.3(4) . . . . ?
F4 C6 C7 F6 163.5(3) . . . . ?
F4 C6 C7 C8 -74.8(4) . . . . ?
F5 C7 C8 F7 161.1(3) . . . . ?
F5 C7 C8 F8 -81.0(4) . . . . ?
F5 C7 C8 C9 40.6(4) . . . . ?
F6 C7 C8 F7 43.0(4) . . . . ?
F6 C7 C8 F8 160.8(3) . . . . ?
F6 C7 C8 C9 -77.6(4) . . . . ?
F7 C8 C9 F9 162.7(3) . . . . ?
F7 C8 C9 F10 -79.2(3) . . . . ?
F7 C8 C9 C10 41.9(4) . . . . ?
F8 C8 C9 F9 44.8(4) . . . . ?
F8 C8 C9 F10 162.9(3) . . . . ?
F8 C8 C9 C10 -76.0(4) . . . . ?
F9 C9 C10 F11 160.2(3) . . . . ?
F9 C9 C10 F12 -82.3(3) . . . . ?
F9 C9 C10 C11 39.2(4) . . . . ?
F10 C9 C10 F11 42.2(4) . . . . ?
F10 C9 C10 F12 159.7(3) . . . . ?
F10 C9 C10 C11 -78.8(4) . . . . ?
F11 C10 C11 F13 165.5(3) . . . . ?
F11 C10 C11 F14 -75.5(4) . . . . ?
F11 C10 C11 C12 46.4(5) . . . . ?
F12 C10 C11 F13 48.0(4) . . . . ?
F12 C10 C11 F14 167.0(3) . . . . ?
F12 C10 C11 C12 -71.1(4) . . . . ?
F13 C11 C12 F15 169.0(4) . . . . ?
F13 C11 C12 F16 49.0(5) . . . . ?
F13 C11 C12 F17 -69.2(4) . . . . ?
F14 C11 C12 F15 51.4(5) . . . . ?
F14 C11 C12 F16 -68.6(5) . . . . ?
F14 C11 C12 F17 173.2(3) . . . . ?
O2 C3 C4 C5 70.3(4) . . . . ?
N1 C1 C2 O1 -13.0(5) . . . . ?
N1 C1 C2 O2 169.4(3) . . . . ?
N1 C1 C18 C19 64.6(4) . . . . ?
N2 C22 C23 C24 176.9(3) . . . . ?
N2 C25 C26 Cl1 173.5(3) . . . . ?
N2 C27 C28 Cl2 -179.5(3) . . . . ?
C1 N1 C13 O3 -2.7(5) . . . . ?
C1 N1 C13 O4 175.5(3) . . . . ?
C1 C18 C19 C20 90.4(4) . . . . ?
C1 C18 C19 C24 -90.0(4) . . . . ?
C2 O2 C3 C4 179.4(3) . . . . ?
C2 C1 C18 C19 -58.3(4) . . . . ?
C3 O2 C2 O1 -5.1(5) . . . . ?
C3 O2 C2 C1 172.6(3) . . . . ?
C3 C4 C5 F1 -60.1(4) . . . . ?
C3 C4 C5 F2 57.4(4) . . . . ?
C3 C4 C5 C6 179.9(3) . . . . ?
C4 C5 C6 F3 42.9(4) . . . . ?
C4 C5 C6 F4 159.6(3) . . . . ?
C4 C5 C6 C7 -78.0(4) . . . . ?
C5 C6 C7 F5 -77.5(4) . . . . ?
C5 C6 C7 F6 40.7(4) . . . . ?
C5 C6 C7 C8 162.4(3) . . . . ?
C6 C7 C8 F7 -79.3(4) . . . . ?
C6 C7 C8 F8 38.5(4) . . . . ?
C6 C7 C8 C9 160.1(3) . . . . ?
C7 C8 C9 F9 -77.1(4) . . . . ?
C7 C8 C9 F10 41.0(4) . . . . ?
C7 C8 C9 C10 162.1(3) . . . . ?
C8 C9 C10 F11 -79.2(4) . . . . ?
C8 C9 C10 F12 38.3(4) . . . . ?
C8 C9 C10 C11 159.8(3) . . . . ?
C9 C10 C11 F13 -73.5(4) . . . . ?
C9 C10 C11 F14 45.5(4) . . . . ?
C9 C10 C11 C12 167.4(3) . . . . ?
C10 C11 C12 F15 -71.1(5) . . . . ?
C10 C11 C12 F16 168.8(3) . . . . ?
C10 C11 C12 F17 50.6(5) . . . . ?
C13 O4 C14 C15 63.3(4) . . . . ?
C13 O4 C14 C16 -179.0(3) . . . . ?
C13 O4 C14 C17 -61.3(4) . . . . ?
C13 N1 C1 C2 -154.0(3) . . . . ?
C13 N1 C1 C18 82.7(4) . . . . ?
C14 O4 C13 O3 -6.3(5) . . . . ?
C14 O4 C13 N1 175.7(3) . . . . ?
C18 C1 C2 O1 112.1(4) . . . . ?
C18 C1 C2 O2 -65.5(3) . . . . ?
C18 C19 C20 C21 178.7(3) . . . . ?
C18 C19 C24 C23 -178.5(3) . . . . ?
C19 C20 C21 C22 -1.1(5) . . . . ?
C20 C19 C24 C23 1.1(5) . . . . ?
C20 C21 C22 N2 -176.7(3) . . . . ?
C20 C21 C22 C23 3.0(5) . . . . ?
C21 C22 C23 C24 -2.8(5) . . . . ?
C22 N2 C25 C26 85.5(5) . . . . ?
C22 N2 C27 C28 90.0(5) . . . . ?
C22 C23 C24 C19 0.8(5) . . . . ?
C24 C19 C20 C21 -1.0(5) . . . . ?
C25 N2 C22 C21 176.9(4) . . . . ?
C25 N2 C22 C23 -2.8(5) . . . . ?
C25 N2 C27 C28 -97.9(5) . . . . ?
C27 N2 C22 C21 -11.4(6) . . . . ?
C27 N2 C22 C23 168.9(4) . . . . ?
C27 N2 C25 C26 -86.6(5) . . . . ?

_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.630
_oxdiff_exptl_absorpt_empirical_full_min 0.655
####################################################################### 
# 
# 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_zs3_hklf5
_database_code_depnum_ccdc_archive 'CCDC 2335490'
loop_
_audit_author_name
_audit_author_address
'Farzaneh Fadaei Tirani'
;EPFL
Switzerland
;
_audit_update_record             
;
2024-02-26 deposited with the CCDC.	2024-05-21 downloaded from the CCDC.
;
_audit_creation_date             2018-12-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'

# start Validation Reply Form
_vrf_PLAT084_zs3_hklf5           
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.43 Report
RESPONSE: The quality of this crystal was poor, however, it represents the
          best possible data after multiple recrystallization attempts.
;
_vrf_PLAT340_zs3_hklf5           
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.04292 Ang.  
RESPONSE: The quality of this crystal was poor, however, it represents the
          best possible data after multiple recrystallization attempts.
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H29 Cl2 F21 N2 O4'
_chemical_formula_sum            'C30 H29 Cl2 F21 N2 O4'
_chemical_formula_weight         951.45
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C30 H29 N2 O4 F21 Cl2'
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'
Cl Cl 0.3639 0.7018 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   10.9654(12)
_cell_length_b                   34.582(6)
_cell_length_c                   9.7715(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3705.4(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2938
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      65.0440
_cell_measurement_theta_min      3.7730
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.938
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.332
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2018).
 Numerical absorption correction based on Gaussian integration over
 a multifaceted crystal model/Empirical absorption correction using
 spherical harmonics as implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.706
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1912
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 22 -1 0.0181
1 -22 1 0.0181
3 -1 6 0.1315
-3 1 -6 0.1975
7 7 -1 0.0860
-7 -6 1 0.0332
-2 21 2 0.0658

_exptl_crystal_size_max          0.393
_exptl_crystal_size_mid          0.129
_exptl_crystal_size_min          0.036
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.9795 22.1933 -0.7704 -0.9772 0.1683 -0.1618
0.9795 -22.1933 0.7704 0.9772 -0.1683 0.1618
2.9904 -1.1399 5.9749 0.1686 0.5168 0.8788
-2.9904 1.1399 -5.9749 -0.1686 -0.5168 -0.8788
7.0031 7.1149 -0.9272 0.0211 1.0007 -0.2964
-7.0023 -6.1149 0.9375 -0.0632 -0.9861 0.2953
-1.9837 20.6483 2.2079 -0.9654 0.0838 0.3260

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.1664
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            19475
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.510
_diffrn_reflns_theta_min         3.835
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2665
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      5.00  30.00   1.00    7.50    --   42.00  89.00 143.30   25
  2  ω    -77.00 -14.00   1.00    7.50    --  -42.51 -57.00  90.00   63
  3  ω   -116.00 -19.00   1.00    7.50    --  -42.51 -37.00-180.00   97
  4  ω    -96.00  -3.00   1.00    7.50    --  -42.51 125.00 120.00   93
  5  ω   -118.00 -10.00   1.00    7.50    --  -42.51 -77.00  60.00  108
  6  ω   -117.00 -18.00   1.00    7.50    --  -42.51 -37.00 -90.00   99
  7  ω     23.00  99.00   1.00    7.50    --   42.51-125.00  60.00   76
  8  ω     11.00  36.00   1.00    7.50    --   46.00  84.00 -76.92   25
  9  ω     12.00  37.00   1.00    7.50    --   46.00  81.00-155.96   25
 10  ω     11.00  36.00   1.00    7.50    --   46.00  84.00  49.73   25
 11  ω     17.00  44.00   1.00    7.50    --   50.00  80.00  23.79   27
 12  ω     20.00  45.00   1.00    7.50    --   54.00  81.00 -41.78   25
 13  ω     21.00  46.00   1.00    7.50    --   54.00  78.00 -77.26   25
 14  ω     20.00  45.00   1.00    7.50    --   54.00  81.00-134.94   25
 15  ω     29.00  56.00   1.00    7.50    --   62.00  77.00 108.55   27
 16  ω     29.00  56.00   1.00    7.50    --   62.00  77.00 145.84   27
 17  ω     80.00 124.00   1.00    7.50    --   62.00  77.00 145.84   44
 18  ω     29.00  59.00   1.00    7.50    --   62.00  77.00  63.48   30
 19  ω     34.00  60.00   1.00    7.50    --   66.00  75.00-179.88   26
 20  ω    107.00 134.00   1.00    7.50    --   70.00  77.00 -87.33   27
 21  ω     38.00  64.00   1.00    7.50    --   70.00  73.00-153.85   26
 22  ω     37.00  64.00   1.00    7.50    --   70.00  77.00 -29.35   27
 23  ω     37.00  64.00   1.00    7.50    --   70.00  77.00 -87.33   27
 24  ω     70.00  98.00   1.00    7.50    --   74.00  74.00  -0.86   28
 25  ω     41.00  67.00   1.00    7.50    --   74.00  77.00-119.08   26
 26  ω    122.00 147.00   1.00    7.50    --   74.00  74.00  -0.86   25
 27  ω     42.00  68.00   1.00    7.50    --   74.00  74.00  -0.86   26
 28  ω     41.00  67.00   1.00    7.50    --   74.00  77.00 -50.53   26
 29  ω    108.00 135.00   1.00    7.50    --   74.00  63.00 122.98   27
 30  ω     42.00  69.00   1.00    7.50    --   74.00  76.00-140.88   27
 31  ω     45.00  71.00   1.00    7.50    --   74.00  63.00 122.98   26
 32  ω     45.00  71.00   1.00   30.00    --   78.00  77.00 119.50   26
 33  ω     46.00  72.00   1.00   30.00    --   78.00  74.00  22.60   26
 34  ω     54.00  81.00   1.00   30.00    --   82.00  62.00 -90.98   27
 35  ω     95.00 158.00   1.00   30.00    --   82.00  77.00  58.03   63
 36  ω     49.00  75.00   1.00   30.00    --   82.00  77.00  58.03   26
 37  ω     49.00  77.00   1.00   30.00    --   82.00  77.00 151.65   28
 38  ω    122.00 152.00   1.00   30.00    --   86.00  70.00  35.87   30
 39  ω     55.00  82.00   1.00   30.00    --   86.00  70.00  35.87   27
 40  ω     57.00  84.00   1.00   30.00    --   86.00  66.00  77.02   27
 41  ω     60.00  86.00   1.00   30.00    --   90.00  68.00 -92.73   26
 42  ω     60.00  89.00   1.00   30.00    --   90.00  67.00 173.48   29
 43  ω     60.00  92.00   1.00   30.00    --   90.00  67.00 -34.46   32
 44  ω     62.00  91.00   1.00   30.00    --   94.00  73.00-140.69   29
 45  ω    110.00 169.00   1.00   30.00    --   98.00  67.00-154.16   59
 46  ω     68.00 102.00   1.00   30.00    --   98.00  67.00-154.16   34
 47  ω     66.00  93.00   1.00   30.00    --   98.00  74.00 -71.33   27
 48  ω     67.00  98.00   1.00   30.00    --   98.00  70.00 110.83   31
 49  ω     78.00 178.00   1.00   30.00    --  110.51  77.00 120.00  100
 50  ω    113.00 172.00   1.00   30.00    --  110.51  61.00  90.00   59
 51  ω     82.00 109.00   1.00   30.00    --  110.51  61.00  90.00   27
 52  ω     81.00 174.00   1.00   30.00    --  110.51  61.00-120.00   93
 53  ω     79.00 177.00   1.00   30.00    --  110.51  77.00 -60.00   98
 54  ω     78.00 143.00   1.00   30.00    --  110.51  77.00  30.00   65
 55  ω    110.00 138.00   1.00   30.00    --  110.51 -61.00  30.00   28
 56  ω     39.00 108.00   1.00   30.00    --  110.51 -61.00  30.00   69
 57  ω     97.00 125.00   1.00   30.00    --  110.51 -45.00-150.00   28
 58  ω     38.00  66.00   1.00   30.00    --  110.51 -45.00-150.00   28
 59  ω     82.00 172.00   1.00   30.00    --  110.51  61.00-180.00   90
 60  ω     78.00 152.00   1.00   30.00    --  110.51  77.00 -30.00   74
 61  ω    112.00 153.00   1.00   30.00    --  110.51  77.00  60.00   41
 62  ω     78.00 104.00   1.00   30.00    --  110.51  77.00  60.00   26
 63  ω     58.00 107.00   1.00   30.00    --  110.51 -94.00 120.00   49
 64  ω     32.00 107.00   1.00   30.00    --  110.51 -94.00 -60.00   75
 65  ω     29.00 109.00   1.00   30.00    --  110.51 -94.00  30.00   80
 66  ω     31.00 109.00   1.00   30.00    --  110.51 -94.00-150.00   78
 67  ω     78.00 172.00   1.00   30.00    --  110.51  77.00   0.00   94
 68  ω     83.00 172.00   1.00   30.00    --  110.51  61.00 -90.00   89
 69  ω    120.00 145.00   1.00   30.00    --  110.51  77.00 150.00   25
 70  ω     78.00 105.00   1.00   30.00    --  110.51  77.00 150.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0454535000
_diffrn_orient_matrix_UB_12      -0.0421125000
_diffrn_orient_matrix_UB_13      -0.0025657000
_diffrn_orient_matrix_UB_21      0.1315543000
_diffrn_orient_matrix_UB_22      0.0142009000
_diffrn_orient_matrix_UB_23      0.0233615000
_diffrn_orient_matrix_UB_31      -0.0189130000
_diffrn_orient_matrix_UB_32      -0.0027099000
_diffrn_orient_matrix_UB_33      0.1560226000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.813
_reflns_Friedel_fraction_full    0.946
_reflns_Friedel_fraction_max     0.902
_reflns_number_gt                8863
_reflns_number_total             19475
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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         1.447
_refine_diff_density_min         -0.823
_refine_diff_density_rms         0.213
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.27(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.212
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     566
_refine_ls_number_reflns         19475
_refine_ls_number_restraints     913
_refine_ls_R_factor_all          0.2309
_refine_ls_R_factor_gt           0.1547
_refine_ls_restrained_S_all      1.220
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3789
_refine_ls_wR_factor_ref         0.4328
_refine_special_details          
;
 Refined as a 4-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.193(15)
 0.228(8) 0.254(7) 0.325(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 Cl2A-C30A = Cl2B-C30B
 1.78 with sigma of 0.01
 C28-C27 \\sim C30A-C29A
 with sigma of 0.01
 C30B-C29B \\sim C30A-C29A
 with sigma of 0.01
 C29A-Cl2A \\sim Cl2B-C29B
 with sigma of 0.01
 C27-N2 \\sim C29A-N2
 with sigma of 0.01
 C28-N2 \\sim N2-C30A
 with sigma of 0.01
 C29A-N2 \\sim N2-C29B
 with sigma of 0.01
 Cl1-C27 \\sim Cl2A-C29A
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.001 and sigma
for terminal atoms of 0.002
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(Cl2B)=Sof(C29B)=Sof(H29C)=Sof(H29D)=Sof(C30B)=Sof(H30C)=Sof(H30D)=1-FVAR(1)
 Sof(Cl2A)=Sof(C29A)=Sof(H29A)=Sof(H29B)=Sof(C30A)=Sof(H30A)=Sof(H30B)=FVAR(1)
7.a Ternary CH refined with riding coordinates:
 C1(H1A)
7.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C20(H20A,H20B), C27(H27A,H27B), C28(H28A,H28B),
 C29A(H29A,H29B), C29B(H29C,H29D), C30A(H30A,H30B), C30B(H30C,H30D)
7.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C22(H22), C23(H23), C25(H25), C26(H26)
7.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
Cl1 Cl 0.3552(8) 0.9297(3) 0.9854(15) 0.074(2) Uani 1 1 d D U . . .
Cl2A Cl 0.3243(14) 0.7372(4) 1.025(2) 0.057(2) Uani 0.62(2) 1 d D U P A 1
Cl2B Cl 0.281(2) 0.7328(6) 0.972(3) 0.058(2) Uani 0.38(2) 1 d D U P A 2
F1 F 0.5832(12) 0.7112(4) 0.216(2) 0.044(2) Uani 1 1 d . U . . .
F2 F 0.6039(13) 0.6796(5) 0.415(2) 0.046(2) Uani 1 1 d . U . . .
F3 F 0.6676(12) 0.6432(4) 0.085(2) 0.046(2) Uani 1 1 d . U . . .
F4 F 0.4898(12) 0.6465(5) 0.182(2) 0.046(2) Uani 1 1 d . U . . .
F5 F 0.7498(14) 0.6082(4) 0.340(2) 0.046(2) Uani 1 1 d . U . . .
F6 F 0.5550(13) 0.6024(5) 0.385(2) 0.049(2) Uani 1 1 d . U . . .
F7 F 0.5363(12) 0.5732(4) 0.105(2) 0.047(2) Uani 1 1 d . U . . .
F8 F 0.7293(12) 0.5678(4) 0.121(2) 0.044(2) Uani 1 1 d . U . . .
F9 F 0.6920(13) 0.5328(5) 0.384(2) 0.048(2) Uani 1 1 d . U . . .
F10 F 0.5002(13) 0.5288(4) 0.313(2) 0.048(2) Uani 1 1 d . U . . .
F11 F 0.5892(14) 0.4980(5) 0.069(2) 0.049(2) Uani 1 1 d . U . . .
F12 F 0.7628(12) 0.4918(4) 0.169(2) 0.047(2) Uani 1 1 d . U . . .
F13 F 0.6278(13) 0.4582(5) 0.391(2) 0.047(2) Uani 1 1 d . U . . .
F14 F 0.4780(11) 0.4552(4) 0.243(2) 0.046(2) Uani 1 1 d . U . . .
F15 F 0.6566(13) 0.4232(5) 0.056(2) 0.049(2) Uani 1 1 d . U . . .
F16 F 0.7679(11) 0.4155(4) 0.238(2) 0.047(2) Uani 1 1 d . U . . .
F17 F 0.5615(12) 0.3809(5) 0.365(2) 0.051(2) Uani 1 1 d . U . . .
F18 F 0.4751(12) 0.3818(5) 0.167(2) 0.049(2) Uani 1 1 d . U . . .
F19 F 0.6812(16) 0.3465(5) 0.062(2) 0.060(3) Uani 1 1 d . U . . .
F20 F 0.7459(14) 0.3385(5) 0.265(2) 0.055(3) Uani 1 1 d . U . . .
F21 F 0.5740(14) 0.3150(5) 0.210(2) 0.053(3) Uani 1 1 d . U . . .
O1 O 0.8420(15) 0.8022(5) 0.427(3) 0.041(3) Uani 1 1 d . U . . .
O2 O 0.7689(15) 0.7606(5) 0.274(3) 0.0406(16) Uani 1 1 d . U . . .
O3 O 0.7270(15) 0.8914(5) 0.074(3) 0.040(3) Uani 1 1 d . U . . .
O4 O 0.8123(14) 0.9261(5) 0.246(2) 0.0392(19) Uani 1 1 d . U . . .
N1 N 0.7655(18) 0.8644(6) 0.279(3) 0.0399(17) Uani 1 1 d . U . . .
H1 H 0.786291 0.869211 0.364700 0.048 Uiso 1 1 calc R . . . .
N2 N 0.368(2) 0.8291(4) 0.776(4) 0.0543(18) Uani 1 1 d D U . . .
C1 C 0.732(2) 0.8268(8) 0.244(4) 0.0408(15) Uani 1 1 d . U . . .
H1A H 0.756775 0.823385 0.146695 0.049 Uiso 1 1 calc R . . . .
C2 C 0.787(2) 0.7962(8) 0.316(4) 0.0404(16) Uani 1 1 d . U . . .
C3 C 0.812(2) 0.7291(8) 0.350(4) 0.0412(17) Uani 1 1 d . U . . .
H3A H 0.775765 0.730061 0.443322 0.049 Uiso 1 1 calc R . . . .
H3B H 0.901438 0.731172 0.360057 0.049 Uiso 1 1 calc R . . . .
C4 C 0.781(2) 0.6915(8) 0.285(4) 0.0419(17) Uani 1 1 d . U . . .
H4A H 0.827123 0.670638 0.331634 0.050 Uiso 1 1 calc R . . . .
H4B H 0.806857 0.692069 0.188386 0.050 Uiso 1 1 calc R . . . .
C5 C 0.647(2) 0.6821(8) 0.292(4) 0.0430(15) Uani 1 1 d . U . . .
C6 C 0.608(2) 0.6450(8) 0.203(4) 0.0437(14) Uani 1 1 d . U . . .
C7 C 0.633(2) 0.6057(8) 0.284(4) 0.0443(14) Uani 1 1 d . U . . .
C8 C 0.629(2) 0.5697(8) 0.193(4) 0.0444(14) Uani 1 1 d . U . . .
C9 C 0.617(2) 0.5319(8) 0.273(4) 0.0452(14) Uani 1 1 d . U . . .
C10 C 0.647(2) 0.4951(8) 0.191(4) 0.0452(14) Uani 1 1 d . U . . .
C11 C 0.595(2) 0.4564(9) 0.262(4) 0.0457(14) Uani 1 1 d . U . . .
C12 C 0.653(2) 0.4192(9) 0.194(4) 0.0469(15) Uani 1 1 d . U . . .
C13 C 0.585(2) 0.3826(9) 0.232(4) 0.0490(16) Uani 1 1 d . U . . .
C14 C 0.646(2) 0.3438(9) 0.192(4) 0.0518(18) Uani 1 1 d . U . . .
C15 C 0.768(2) 0.8938(8) 0.188(4) 0.0393(17) Uani 1 1 d . U . . .
C16 C 0.814(2) 0.9616(8) 0.175(4) 0.039(2) Uani 1 1 d . U . . .
C17 C 0.888(2) 0.9592(8) 0.044(4) 0.039(3) Uani 1 1 d . U . . .
H17A H 0.963649 0.945125 0.061635 0.058 Uiso 1 1 calc GR . . . .
H17B H 0.906553 0.985308 0.011701 0.058 Uiso 1 1 calc GR . . . .
H17C H 0.840234 0.945469 -0.025776 0.058 Uiso 1 1 calc GR . . . .
C18 C 0.873(2) 0.9904(8) 0.276(4) 0.040(3) Uani 1 1 d . U . . .
H18A H 0.821488 0.992654 0.357702 0.060 Uiso 1 1 calc GR . . . .
H18B H 0.880447 1.015747 0.232142 0.060 Uiso 1 1 calc GR . . . .
H18C H 0.953798 0.980991 0.302262 0.060 Uiso 1 1 calc GR . . . .
C19 C 0.684(2) 0.9760(8) 0.147(4) 0.040(3) Uani 1 1 d . U . . .
H19A H 0.650116 0.962172 0.068604 0.060 Uiso 1 1 calc GR . . . .
H19B H 0.685860 1.003800 0.127843 0.060 Uiso 1 1 calc GR . . . .
H19C H 0.633137 0.971242 0.228068 0.060 Uiso 1 1 calc GR . . . .
C20 C 0.588(2) 0.8224(8) 0.247(4) 0.0424(17) Uani 1 1 d . U . . .
H20A H 0.551175 0.843433 0.191357 0.051 Uiso 1 1 calc R . . . .
H20B H 0.565140 0.797519 0.203490 0.051 Uiso 1 1 calc R . . . .
C21 C 0.534(2) 0.8238(8) 0.390(4) 0.0443(17) Uani 1 1 d . U . . .
C22 C 0.518(2) 0.7910(9) 0.461(4) 0.0457(19) Uani 1 1 d . U . . .
H22 H 0.538649 0.766787 0.421444 0.055 Uiso 1 1 calc R . . . .
C23 C 0.467(2) 0.7930(9) 0.599(4) 0.0476(19) Uani 1 1 d . U . . .
H23 H 0.460946 0.770043 0.652047 0.057 Uiso 1 1 calc R . . . .
C24 C 0.429(3) 0.8275(9) 0.655(4) 0.0495(17) Uani 1 1 d . U . . .
C25 C 0.449(2) 0.8602(9) 0.576(4) 0.0473(19) Uani 1 1 d . U . . .
H25 H 0.426473 0.884573 0.612640 0.057 Uiso 1 1 calc R . . . .
C26 C 0.503(2) 0.8594(9) 0.444(4) 0.0456(19) Uani 1 1 d . U . . .
H26 H 0.515676 0.882547 0.393363 0.055 Uiso 1 1 calc R . . . .
C27 C 0.325(3) 0.8667(9) 0.836(4) 0.057(2) Uani 1 1 d D U . . .
H27A H 0.290852 0.882996 0.761901 0.068 Uiso 1 1 calc R . . . .
H27B H 0.259221 0.861574 0.902671 0.068 Uiso 1 1 calc R . . . .
C28 C 0.425(3) 0.8883(9) 0.905(5) 0.060(2) Uani 1 1 d D U . . .
H28A H 0.487106 0.896654 0.837887 0.072 Uiso 1 1 calc R . . . .
H28B H 0.465059 0.871776 0.974729 0.072 Uiso 1 1 calc R . . . .
C29A C 0.382(3) 0.7991(12) 0.885(5) 0.0554(19) Uani 0.62(2) 1 d D U P A 1
H29A H 0.454153 0.783048 0.862781 0.066 Uiso 0.62(2) 1 calc R . P A 1
H29B H 0.399016 0.812347 0.972903 0.066 Uiso 0.62(2) 1 calc R . P A 1
C29B C 0.296(5) 0.7975(17) 0.838(8) 0.0553(19) Uani 0.38(2) 1 d D U P A 2
H29C H 0.287300 0.776715 0.768674 0.066 Uiso 0.38(2) 1 calc R . P A 2
H29D H 0.213438 0.807455 0.857979 0.066 Uiso 0.38(2) 1 calc R . P A 2
C30A C 0.275(3) 0.7733(12) 0.904(5) 0.056(2) Uani 0.62(2) 1 d D U P A 1
H30A H 0.251902 0.761179 0.815916 0.067 Uiso 0.62(2) 1 calc R . P A 1
H30B H 0.204817 0.787941 0.939930 0.067 Uiso 0.62(2) 1 calc R . P A 1
C30B C 0.347(6) 0.7803(13) 0.965(8) 0.056(2) Uani 0.38(2) 1 d D U P A 2
H30C H 0.324184 0.795753 1.046413 0.067 Uiso 0.38(2) 1 calc R . P A 2
H30D H 0.437524 0.778758 0.960320 0.067 Uiso 0.38(2) 1 calc R . P A 2


_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
Cl1 C28 1.80(3) . ?
Cl2A C30A 1.80(2) . ?
Cl2B C30B 1.80(2) . ?
F1 C5 1.43(3) . ?
F2 C5 1.29(4) . ?
F3 C6 1.33(4) . ?
F4 C6 1.31(3) . ?
F5 C7 1.40(3) . ?
F6 C7 1.31(4) . ?
F7 C8 1.34(4) . ?
F8 C8 1.31(3) . ?
F9 C9 1.36(4) . ?
F10 C9 1.34(3) . ?
F11 C10 1.35(4) . ?
F12 C10 1.30(3) . ?
F13 C11 1.31(4) . ?
F14 C11 1.30(3) . ?
F15 C12 1.35(4) . ?
F16 C12 1.34(3) . ?
F17 C13 1.32(4) . ?
F18 C13 1.36(3) . ?
F19 C14 1.33(4) . ?
F20 C14 1.32(4) . ?
F21 C14 1.28(3) . ?
O1 C2 1.26(4) . ?
O2 C2 1.31(3) . ?
O2 C3 1.40(4) . ?
O3 C15 1.20(4) . ?
O4 C15 1.34(3) . ?
O4 C16 1.41(4) . ?
N1 H1 0.8800 . ?
N1 C1 1.39(3) . ?
N1 C15 1.35(4) . ?
N2 C24 1.36(5) . ?
N2 C27 1.50(3) . ?
N2 C29A 1.49(4) . ?
N2 C29B 1.47(4) . ?
C1 H1A 1.0000 . ?
C1 C2 1.40(4) . ?
C1 C20 1.59(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.49(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.51(3) . ?
C5 C6 1.61(4) . ?
C6 C7 1.60(4) . ?
C7 C8 1.53(4) . ?
C8 C9 1.53(4) . ?
C9 C10 1.54(4) . ?
C10 C11 1.60(4) . ?
C11 C12 1.58(4) . ?
C12 C13 1.52(4) . ?
C13 C14 1.55(4) . ?
C16 C17 1.52(5) . ?
C16 C18 1.54(5) . ?
C16 C19 1.53(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.52(5) . ?
C21 C22 1.34(4) . ?
C21 C26 1.38(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.47(5) . ?
C23 H23 0.9500 . ?
C23 C24 1.38(4) . ?
C24 C25 1.39(5) . ?
C25 H25 0.9500 . ?
C25 C26 1.42(5) . ?
C26 H26 0.9500 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.49(4) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29A H29A 0.9900 . ?
C29A H29B 0.9900 . ?
C29A C30A 1.48(4) . ?
C29B H29C 0.9900 . ?
C29B H29D 0.9900 . ?
C29B C30B 1.49(4) . ?
C30A H30A 0.9900 . ?
C30A H30B 0.9900 . ?
C30B H30C 0.9900 . ?
C30B H30D 0.9900 . ?

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
C2 O2 C3 121(3) . . ?
C15 O4 C16 122(3) . . ?
C1 N1 H1 118.5 . . ?
C15 N1 H1 118.5 . . ?
C15 N1 C1 123(3) . . ?
C24 N2 C27 122(2) . . ?
C24 N2 C29A 123(3) . . ?
C24 N2 C29B 126(4) . . ?
C29A N2 C27 111(4) . . ?
C29B N2 C27 109(4) . . ?
N1 C1 H1A 105.8 . . ?
N1 C1 C2 118(3) . . ?
N1 C1 C20 110(2) . . ?
C2 C1 H1A 105.8 . . ?
C2 C1 C20 110(2) . . ?
C20 C1 H1A 105.8 . . ?
O1 C2 O2 120(3) . . ?
O1 C2 C1 121(3) . . ?
O2 C2 C1 119(3) . . ?
O2 C3 H3A 109.2 . . ?
O2 C3 H3B 109.2 . . ?
O2 C3 C4 112(3) . . ?
H3A C3 H3B 107.9 . . ?
C4 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
C3 C4 H4A 108.9 . . ?
C3 C4 H4B 108.9 . . ?
C3 C4 C5 113(2) . . ?
H4A C4 H4B 107.8 . . ?
C5 C4 H4A 108.9 . . ?
C5 C4 H4B 108.9 . . ?
F1 C5 C4 108(2) . . ?
F1 C5 C6 99(2) . . ?
F2 C5 F1 110(2) . . ?
F2 C5 C4 114(3) . . ?
F2 C5 C6 111(2) . . ?
C4 C5 C6 114(2) . . ?
F3 C6 C5 112(2) . . ?
F3 C6 C7 108(2) . . ?
F4 C6 F3 111(3) . . ?
F4 C6 C5 108(2) . . ?
F4 C6 C7 106(2) . . ?
C7 C6 C5 111(3) . . ?
F5 C7 C6 107(2) . . ?
F5 C7 C8 108(2) . . ?
F6 C7 F5 108(3) . . ?
F6 C7 C6 110(2) . . ?
F6 C7 C8 110(2) . . ?
C8 C7 C6 113(3) . . ?
F7 C8 C7 109(2) . . ?
F7 C8 C9 110(2) . . ?
F8 C8 F7 107(3) . . ?
F8 C8 C7 109(2) . . ?
F8 C8 C9 108(2) . . ?
C9 C8 C7 114(3) . . ?
F9 C9 C8 110(2) . . ?
F9 C9 C10 108(2) . . ?
F10 C9 F9 111(3) . . ?
F10 C9 C8 107(2) . . ?
F10 C9 C10 107(2) . . ?
C8 C9 C10 115(3) . . ?
F11 C10 C9 107(2) . . ?
F11 C10 C11 106(2) . . ?
F12 C10 F11 109(3) . . ?
F12 C10 C9 111(2) . . ?
F12 C10 C11 110(2) . . ?
C9 C10 C11 113(3) . . ?
F13 C11 C10 106(2) . . ?
F13 C11 C12 110(2) . . ?
F14 C11 F13 114(3) . . ?
F14 C11 C10 108(2) . . ?
F14 C11 C12 108(2) . . ?
C12 C11 C10 111(2) . . ?
F15 C12 C11 110(3) . . ?
F15 C12 C13 110(3) . . ?
F16 C12 F15 108(2) . . ?
F16 C12 C11 109(2) . . ?
F16 C12 C13 108(2) . . ?
C13 C12 C11 112(2) . . ?
F17 C13 F18 107(2) . . ?
F17 C13 C12 112(3) . . ?
F17 C13 C14 107(3) . . ?
F18 C13 C12 110(3) . . ?
F18 C13 C14 104(2) . . ?
C12 C13 C14 116(2) . . ?
F19 C14 C13 108(3) . . ?
F20 C14 F19 106(2) . . ?
F20 C14 C13 110(3) . . ?
F21 C14 F19 112(3) . . ?
F21 C14 F20 109(3) . . ?
F21 C14 C13 112(2) . . ?
O3 C15 O4 125(3) . . ?
O3 C15 N1 124(3) . . ?
O4 C15 N1 111(3) . . ?
O4 C16 C17 112(2) . . ?
O4 C16 C18 105(3) . . ?
O4 C16 C19 111(2) . . ?
C17 C16 C18 111(2) . . ?
C17 C16 C19 111(3) . . ?
C19 C16 C18 107(2) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C1 C20 H20A 109.0 . . ?
C1 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
C21 C20 C1 113(3) . . ?
C21 C20 H20A 109.0 . . ?
C21 C20 H20B 109.0 . . ?
C22 C21 C20 120(3) . . ?
C22 C21 C26 122(3) . . ?
C26 C21 C20 118(3) . . ?
C21 C22 H22 120.5 . . ?
C21 C22 C23 119(3) . . ?
C23 C22 H22 120.5 . . ?
C22 C23 H23 119.2 . . ?
C24 C23 C22 122(3) . . ?
C24 C23 H23 119.2 . . ?
N2 C24 C23 122(3) . . ?
N2 C24 C25 122(3) . . ?
C23 C24 C25 116(4) . . ?
C24 C25 H25 118.0 . . ?
C24 C25 C26 124(3) . . ?
C26 C25 H25 118.0 . . ?
C21 C26 C25 118(3) . . ?
C21 C26 H26 121.2 . . ?
C25 C26 H26 121.2 . . ?
N2 C27 H27A 109.1 . . ?
N2 C27 H27B 109.1 . . ?
H27A C27 H27B 107.9 . . ?
C28 C27 N2 112(2) . . ?
C28 C27 H27A 109.1 . . ?
C28 C27 H27B 109.1 . . ?
Cl1 C28 H28A 110.4 . . ?
Cl1 C28 H28B 110.4 . . ?
C27 C28 Cl1 106(2) . . ?
C27 C28 H28A 110.4 . . ?
C27 C28 H28B 110.4 . . ?
H28A C28 H28B 108.6 . . ?
N2 C29A H29A 108.5 . . ?
N2 C29A H29B 108.5 . . ?
H29A C29A H29B 107.5 . . ?
C30A C29A N2 115(3) . . ?
C30A C29A H29A 108.5 . . ?
C30A C29A H29B 108.5 . . ?
N2 C29B H29C 108.4 . . ?
N2 C29B H29D 108.4 . . ?
N2 C29B C30B 116(5) . . ?
H29C C29B H29D 107.4 . . ?
C30B C29B H29C 108.4 . . ?
C30B C29B H29D 108.4 . . ?
Cl2A C30A H30A 110.7 . . ?
Cl2A C30A H30B 110.7 . . ?
C29A C30A Cl2A 105(2) . . ?
C29A C30A H30A 110.7 . . ?
C29A C30A H30B 110.7 . . ?
H30A C30A H30B 108.8 . . ?
Cl2B C30B H30C 111.0 . . ?
Cl2B C30B H30D 111.0 . . ?
C29B C30B Cl2B 104(2) . . ?
C29B C30B H30C 111.0 . . ?
C29B C30B H30D 111.0 . . ?
H30C C30B H30D 109.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O3 0.88 2.19 3.03(4) 159.1 4_655 yes

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
F1 C5 C6 F3 75(2) . . . . ?
F1 C5 C6 F4 -47(3) . . . . ?
F1 C5 C6 C7 -163.8(19) . . . . ?
F2 C5 C6 F3 -169(2) . . . . ?
F2 C5 C6 F4 69(3) . . . . ?
F2 C5 C6 C7 -48(3) . . . . ?
F3 C6 C7 F5 77(3) . . . . ?
F3 C6 C7 F6 -166(2) . . . . ?
F3 C6 C7 C8 -42(3) . . . . ?
F4 C6 C7 F5 -164(3) . . . . ?
F4 C6 C7 F6 -47(3) . . . . ?
F4 C6 C7 C8 77(3) . . . . ?
F5 C7 C8 F7 -159(2) . . . . ?
F5 C7 C8 F8 -43(3) . . . . ?
F5 C7 C8 C9 77(3) . . . . ?
F6 C7 C8 F7 83(3) . . . . ?
F6 C7 C8 F8 -161(3) . . . . ?
F6 C7 C8 C9 -40(3) . . . . ?
F7 C8 C9 F9 -165(2) . . . . ?
F7 C8 C9 F10 -45(3) . . . . ?
F7 C8 C9 C10 73(3) . . . . ?
F8 C8 C9 F9 78(3) . . . . ?
F8 C8 C9 F10 -162(3) . . . . ?
F8 C8 C9 C10 -43(3) . . . . ?
F9 C9 C10 F11 -168(2) . . . . ?
F9 C9 C10 F12 -50(3) . . . . ?
F9 C9 C10 C11 75(3) . . . . ?
F10 C9 C10 F11 73(3) . . . . ?
F10 C9 C10 F12 -168(3) . . . . ?
F10 C9 C10 C11 -44(3) . . . . ?
F11 C10 C11 F13 -165(2) . . . . ?
F11 C10 C11 F14 -43(3) . . . . ?
F11 C10 C11 C12 76(3) . . . . ?
F12 C10 C11 F13 77(3) . . . . ?
F12 C10 C11 F14 -160(3) . . . . ?
F12 C10 C11 C12 -42(4) . . . . ?
F13 C11 C12 F15 -159(2) . . . . ?
F13 C11 C12 F16 -42(3) . . . . ?
F13 C11 C12 C13 77(3) . . . . ?
F14 C11 C12 F15 76(3) . . . . ?
F14 C11 C12 F16 -166(3) . . . . ?
F14 C11 C12 C13 -47(4) . . . . ?
F15 C12 C13 F17 -170(2) . . . . ?
F15 C12 C13 F18 -51(3) . . . . ?
F15 C12 C13 C14 67(3) . . . . ?
F16 C12 C13 F17 73(3) . . . . ?
F16 C12 C13 F18 -168(3) . . . . ?
F16 C12 C13 C14 -50(4) . . . . ?
F17 C13 C14 F19 -174(2) . . . . ?
F17 C13 C14 F20 -58(3) . . . . ?
F17 C13 C14 F21 63(4) . . . . ?
F18 C13 C14 F19 73(3) . . . . ?
F18 C13 C14 F20 -171(3) . . . . ?
F18 C13 C14 F21 -50(4) . . . . ?
O2 C3 C4 C5 -70(3) . . . . ?
N1 C1 C2 O1 16(4) . . . . ?
N1 C1 C2 O2 -171(2) . . . . ?
N1 C1 C20 C21 -70(3) . . . . ?
N2 C24 C25 C26 -174(3) . . . . ?
N2 C27 C28 Cl1 -174(3) . . . . ?
N2 C29A C30A Cl2A 173(4) . . . . ?
N2 C29B C30B Cl2B -157(5) . . . . ?
C1 N1 C15 O3 9(4) . . . . ?
C1 N1 C15 O4 -175(2) . . . . ?
C1 C20 C21 C22 -92(3) . . . . ?
C1 C20 C21 C26 89(3) . . . . ?
C2 O2 C3 C4 179(2) . . . . ?
C2 C1 C20 C21 62(3) . . . . ?
C3 O2 C2 O1 -1(3) . . . . ?
C3 O2 C2 C1 -174(2) . . . . ?
C3 C4 C5 F1 62(4) . . . . ?
C3 C4 C5 F2 -60(3) . . . . ?
C3 C4 C5 C6 171(3) . . . . ?
C4 C5 C6 F3 -39(4) . . . . ?
C4 C5 C6 F4 -161(3) . . . . ?
C4 C5 C6 C7 82(3) . . . . ?
C5 C6 C7 F5 -46(3) . . . . ?
C5 C6 C7 F6 71(3) . . . . ?
C5 C6 C7 C8 -165(2) . . . . ?
C6 C7 C8 F7 -41(3) . . . . ?
C6 C7 C8 F8 76(3) . . . . ?
C6 C7 C8 C9 -163.9(19) . . . . ?
C7 C8 C9 F9 -43(3) . . . . ?
C7 C8 C9 F10 77(3) . . . . ?
C7 C8 C9 C10 -164(2) . . . . ?
C8 C9 C10 F11 -46(3) . . . . ?
C8 C9 C10 F12 73(3) . . . . ?
C8 C9 C10 C11 -163(2) . . . . ?
C9 C10 C11 F13 -48(3) . . . . ?
C9 C10 C11 F14 75(3) . . . . ?
C9 C10 C11 C12 -167(2) . . . . ?
C10 C11 C12 F15 -42(3) . . . . ?
C10 C11 C12 F16 75(3) . . . . ?
C10 C11 C12 C13 -166(3) . . . . ?
C11 C12 C13 F17 -46(3) . . . . ?
C11 C12 C13 F18 72(3) . . . . ?
C11 C12 C13 C14 -170(3) . . . . ?
C12 C13 C14 F19 -47(4) . . . . ?
C12 C13 C14 F20 68(4) . . . . ?
C12 C13 C14 F21 -171(3) . . . . ?
C15 O4 C16 C17 -60(3) . . . . ?
C15 O4 C16 C18 -180(2) . . . . ?
C15 O4 C16 C19 65(3) . . . . ?
C15 N1 C1 C2 149(3) . . . . ?
C15 N1 C1 C20 -83(3) . . . . ?
C16 O4 C15 O3 1(4) . . . . ?
C16 O4 C15 N1 -174(2) . . . . ?
C20 C1 C2 O1 -112(3) . . . . ?
C20 C1 C2 O2 61(4) . . . . ?
C20 C21 C22 C23 180(2) . . . . ?
C20 C21 C26 C25 178(3) . . . . ?
C21 C22 C23 C24 5(4) . . . . ?
C22 C21 C26 C25 -1(4) . . . . ?
C22 C23 C24 N2 172(3) . . . . ?
C22 C23 C24 C25 -5(4) . . . . ?
C23 C24 C25 C26 2(5) . . . . ?
C24 N2 C27 C28 -80(4) . . . . ?
C24 N2 C29A C30A -108(5) . . . . ?
C24 N2 C29B C30B 112(7) . . . . ?
C24 C25 C26 C21 1(5) . . . . ?
C26 C21 C22 C23 -2(4) . . . . ?
C27 N2 C24 C23 -179(3) . . . . ?
C27 N2 C24 C25 -3(4) . . . . ?
C27 N2 C29A C30A 95(5) . . . . ?
C27 N2 C29B C30B -90(6) . . . . ?
C29A N2 C24 C23 26(4) . . . . ?
C29A N2 C24 C25 -157(3) . . . . ?
C29A N2 C27 C28 77(4) . . . . ?
C29B N2 C24 C23 -24(5) . . . . ?
C29B N2 C24 C25 152(4) . . . . ?
C29B N2 C27 C28 122(4) . . . . ?

_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 5.361
_oxdiff_exptl_absorpt_empirical_full_min 0.247
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               4
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.193(15) 13590 46462 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.228(8) 0 43036 nmt -1.0004 -0.0013 -0.0001 0.0138 -0.9999 -0.1948 0.0011
-0.0144 0.9996
3 0.254(7) 0 39990 nmt -0.9999 -0.0011 -0.0003 -0.0128 0.9920 -0.4009 0.0000
-0.0307 -0.9940
4 0.325(10) 0 45071 nmt 1.0000 -0.0004 0.0001 0.0038 0.9996 0.1065 -0.0007
-0.0082 0.9983

_twin_special_details            
;
Component 2 rotated by 179.7469° 
 around [-0.00 -0.09 1.00] (reciprocal) or [0.00 -0.01 1.00] (direct)
Component 3 rotated by 179.9905° 
 around [-0.00 1.00 -0.02] (reciprocal) or [-0.01 0.98 -0.19] (direct)
Component 4 rotated by 1.6689° 
 around [-1.00 0.08 0.04] (reciprocal) or [-1.00 0.01 0.05] (direct)
;
