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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_audit_block_doi                 10.5517/ccdc.csd.cc245s26
_database_code_depnum_ccdc_archive 'CCDC 1971757'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D0CC07385G 2021
loop_
_audit_author_name
_audit_author_address
'HEMANT RAWAT'
;TATA INSTITUTE OF FUNDAMENTAL RESEARCH HYDERABAD
India
;
_audit_update_record             
;
2020-11-28 deposited with the CCDC.	2021-05-04 downloaded from the CCDC.
;
_audit_creation_date             2020-04-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H38 N2, F3.97 Sb, 2.03(F)'
_chemical_formula_sum            'C22 H38 F6 N2 Sb'
_chemical_formula_weight         566.29
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   15.5683(14)
_cell_length_b                   15.5783(14)
_cell_length_c                   10.020(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2430.2(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7107
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.7570
_cell_measurement_theta_min      3.5250
_shelx_estimated_absorpt_T_max   0.851
_shelx_estimated_absorpt_T_min   0.771
_exptl_absorpt_coefficient_mu    1.192
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64597
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1156
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0925
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.847
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            25957
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.845
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.030
_diffrn_reflns_theta_min         2.615
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 7.9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.847
_diffrn_measurement_device_type  'Bruker SMART CCD 1K area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.786
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.843
_reflns_number_gt                4059
_reflns_number_total             5714
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.742
_refine_diff_density_min         -0.732
_refine_diff_density_rms         0.095
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.50(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     513
_refine_ls_number_reflns         5714
_refine_ls_number_restraints     1208
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0396
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0639P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.1079
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.50(6)
 0.50(6)
2. 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
3. Restrained distances
 Sb1-F1 \\sim Sb1-F2 \\sim Sb1-F3 \\sim Sb1-F4 \\sim Sb1-F5 \\sim Sb1-F6 \\sim
Sb1-F1' \\sim Sb1-F2' \\sim Sb1-
 F3' \\sim Sb1-F4'
 with sigma of 0.02
 Sb1-F1 \\sim Sb1-F5' \\sim Sb1-F6' \\sim Sb1-F1'' \\sim Sb1-F2'' \\sim
Sb1-F3'' \\sim Sb1-F4'' \\sim Sb1-
 F5''
 with sigma of 0.02
 Sb1-F1 \\sim Sb1-F6''
 with sigma of 0.02
 F1-F2 \\sim F1'-F2' \\sim F3-F5 \\sim F3'-F5' \\sim F4-F6 \\sim F4'-F6' \\sim
F3''-F5'' \\sim F4''-F6''
 with sigma of 0.02
 F1-F3 \\sim F1-F4 \\sim F1-F5 \\sim F1-F6 \\sim F1'-F3' \\sim F1'-F4' \\sim
F1'-F5' \\sim F1'-F6' \\sim F2-F3
 \\sim F2-F4 \\sim F2-F5
 with sigma of 0.02
 F1-F3 \\sim F2-F6 \\sim F2'-F3' \\sim F2'-F4' \\sim F2'-F5' \\sim F2'-F6'
\\sim F1''-F3'' \\sim F1''-F4''
 \\sim F1''-F5''
 with sigma of 0.02
 F1-F3 \\sim F1''-F6'' \\sim F2''-F3'' \\sim F2''-F4'' \\sim F2''-F5'' \\sim
F2''-F6''
 with sigma of 0.02
 N2-C3 \\sim N2-C3A
 with sigma of 0.02
4. Rigid bond restraints
 C12, C14, C13, C13A, C15, C15A, C16, C16A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C5, C7, C6, C6A, C9, C9A, C8, C8A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C3, C3A, C4, C4A, C22, C22A, C21, C21A, C20, C20A, C19, C19A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
F1 \\sim F2 \\sim F3 \\sim F4 \\sim F5 \\sim F6 \\sim F1' \\sim F2' \\sim F3'
\\sim F4' \\sim F5' \\sim F6' \\sim F2'': within 2.9A with sigma of 0.01 and
sigma for terminal atoms of 0.02
F1'' \\sim F2'' \\sim F3'' \\sim F4'' \\sim F5'' \\sim F6'': within 3.5A with
sigma of 0.01 and sigma for terminal atoms of 0.02
C12 \\sim C14 \\sim C13 \\sim C13A \\sim C15 \\sim C15A \\sim C16 \\sim C16A:
within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04
C5 \\sim C7 \\sim C6 \\sim C6A \\sim C9 \\sim C9A \\sim C8 \\sim C8A: within
1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
C3 \\sim C3A \\sim C4 \\sim C4A \\sim C22 \\sim C22A \\sim C21 \\sim C21A \\sim
C20 \\sim C20A \\sim C19 \\sim C19A: within 1.7A with sigma of 0.01 and sigma
for terminal atoms of 0.02
6. Same fragment restrains
{C3A, C4A, C22A, C21A, C20A, C19A} sigma for 1-2: 0.02, 1-3: 0.04
as
{C3, C4, C22, C21, C20, C19}
7. Others
 Sof(F1')=Sof(F2')=Sof(F3')=Sof(F4')=Sof(F5')=Sof(F6')=0.7*(1-FVAR(2))
 Sof(F1'')=Sof(F2'')=Sof(F3'')=Sof(F4'')=Sof(F5'')=Sof(F6'')=0.3*(1-FVAR(2))
 Sof(F1)=Sof(F2)=Sof(F3)=Sof(F4)=Sof(F5)=Sof(F6)=FVAR(1)
 Sof(C6A)=Sof(H6AA)=Sof(H6AB)=Sof(C9A)=Sof(H9AA)=Sof(H9AB)=Sof(H9AC)=Sof(C8A)=
 Sof(H8AA)=Sof(H8AB)=Sof(H8AC)=1-FVAR(2)
 Sof(C6)=Sof(H6A)=Sof(H6B)=Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(H9C)=Sof(C8)=Sof(H8A)=
 Sof(H8B)=Sof(H8C)=FVAR(2)
 Sof(C13A)=Sof(H13C)=Sof(H13D)=Sof(C15A)=Sof(H15D)=Sof(H15E)=Sof(H15F)=
 Sof(C16A)=Sof(H16D)=Sof(H16E)=Sof(H16F)=1-FVAR(3)
 Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(H15C)=Sof(C16)=
 Sof(H16A)=Sof(H16B)=Sof(H16C)=FVAR(3)
 Sof(C3A)=Sof(H3A)=Sof(C4A)=Sof(H4A)=Sof(C22A)=Sof(H22C)=Sof(H22D)=Sof(C21A)=
 Sof(H21C)=Sof(H21D)=Sof(C20A)=Sof(H20C)=Sof(H20D)=Sof(C19A)=Sof(H19C)=
 Sof(H19D)=1-FVAR(4)
 Sof(C3)=Sof(H3)=Sof(C4)=Sof(H4)=Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(C21)=
 Sof(H21A)=Sof(H21B)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(C19)=Sof(H19A)=Sof(H19B)=
 FVAR(4)
8.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4), C3A(H3A), C4A(H4A)
8.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C6A(H6AA,H6AB), C13(H13A,H13B), C13A(H13C,H13D), C22(H22A,H22B),
 C21(H21A,H21B), C20(H20A,H20B), C19(H19A,H19B), C22A(H22C,H22D), C21A(H21C,
 H21D), C20A(H20C,H20D), C19A(H19C,H19D)
8.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C10(H10A,H10B,H10C), C18(H18A,H18B,H18C), C17(H17A,H17B,
 H17C), C9(H9A,H9B,H9C), C8(H8A,H8B,H8C), C9A(H9AA,H9AB,H9AC), C8A(H8AA,H8AB,
 H8AC), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C15A(H15D,H15E,H15F),
 C16A(H16D,H16E,H16F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.54776(16) 0.55151(18) 0.5010(9) 0.0357(7) Uani 1 1 d . . . . .
N2 N 0.41368(17) 0.43447(18) 0.5008(10) 0.0400(7) Uani 1 1 d D . . . .
C1 C 0.5642(2) 0.4655(2) 0.5006(11) 0.0363(8) Uani 1 1 d . . . . .
C7 C 0.6615(2) 0.4506(2) 0.5000(12) 0.0460(8) Uani 1 1 d . U . . .
C5 C 0.6268(2) 0.6067(2) 0.4989(11) 0.0462(10) Uani 1 1 d . U . . .
C11 C 0.6332(5) 0.6602(6) 0.3766(8) 0.071(3) Uani 1 1 d . . . . .
H11A H 0.595596 0.708764 0.384602 0.106 Uiso 1 1 calc GR . . . .
H11B H 0.616779 0.626638 0.300391 0.106 Uiso 1 1 calc GR . . . .
H11C H 0.691244 0.679701 0.365860 0.106 Uiso 1 1 calc GR . . . .
C10 C 0.6338(6) 0.6647(7) 0.6234(7) 0.079(3) Uani 1 1 d . . . . .
H10A H 0.595177 0.712421 0.614443 0.118 Uiso 1 1 calc GR . . . .
H10B H 0.691583 0.685557 0.631687 0.118 Uiso 1 1 calc GR . . . .
H10C H 0.618952 0.632286 0.701570 0.118 Uiso 1 1 calc GR . . . .
C2 C 0.49615(17) 0.4070(2) 0.4991(8) 0.0363(9) Uani 1 1 d . . . . .
C14 C 0.49791(19) 0.3080(3) 0.4994(10) 0.0474(10) Uani 1 1 d . U . . .
C12 C 0.3483(2) 0.3636(2) 0.4996(12) 0.0498(10) Uani 1 1 d . U . . .
C18 C 0.2917(6) 0.3657(8) 0.3744(8) 0.073(3) Uani 1 1 d . . . . .
H18A H 0.325812 0.381894 0.298696 0.110 Uiso 1 1 calc GR . . . .
H18B H 0.246308 0.406721 0.386611 0.110 Uiso 1 1 calc GR . . . .
H18C H 0.267415 0.309872 0.359583 0.110 Uiso 1 1 calc GR . . . .
C17 C 0.2930(7) 0.3637(8) 0.6220(9) 0.087(4) Uani 1 1 d . . . . .
H17A H 0.253980 0.316036 0.618541 0.130 Uiso 1 1 calc GR . . . .
H17B H 0.260976 0.416311 0.625976 0.130 Uiso 1 1 calc GR . . . .
H17C H 0.328581 0.358838 0.699870 0.130 Uiso 1 1 calc GR . . . .
C6 C 0.6982(13) 0.5430(14) 0.536(3) 0.055(5) Uani 0.50(2) 1 d . U P A 1
H6A H 0.711352 0.546653 0.630714 0.066 Uiso 0.50(2) 1 calc R . P A 1
H6B H 0.750047 0.554840 0.485836 0.066 Uiso 0.50(2) 1 calc R . P A 1
C9 C 0.6990(11) 0.3867(15) 0.6018(16) 0.055(4) Uani 0.50(2) 1 d . U P A 1
H9A H 0.686684 0.329110 0.573625 0.082 Uiso 0.50(2) 1 calc GR . P A 1
H9B H 0.673659 0.396725 0.687718 0.082 Uiso 0.50(2) 1 calc GR . P A 1
H9C H 0.760080 0.394472 0.607494 0.082 Uiso 0.50(2) 1 calc GR . P A 1
C8 C 0.6944(9) 0.4291(16) 0.3586(15) 0.064(6) Uani 0.50(2) 1 d . U P A 1
H8A H 0.756031 0.429521 0.358188 0.095 Uiso 0.50(2) 1 calc GR . P A 1
H8B H 0.673385 0.471198 0.296620 0.095 Uiso 0.50(2) 1 calc GR . P A 1
H8C H 0.674111 0.373309 0.332884 0.095 Uiso 0.50(2) 1 calc GR . P A 1
C6A C 0.6922(11) 0.5355(14) 0.448(3) 0.047(4) Uani 0.50(2) 1 d . U P A 2
H6AA H 0.693872 0.534792 0.351379 0.057 Uiso 0.50(2) 1 calc R . P A 2
H6AB H 0.749507 0.547522 0.481085 0.057 Uiso 0.50(2) 1 calc R . P A 2
C9A C 0.6861(15) 0.4346(15) 0.641(2) 0.103(8) Uani 0.50(2) 1 d . U P A 2
H9AA H 0.742663 0.410165 0.643735 0.155 Uiso 0.50(2) 1 calc GR . P A 2
H9AB H 0.645888 0.395491 0.680465 0.155 Uiso 0.50(2) 1 calc GR . P A 2
H9AC H 0.685612 0.487797 0.689044 0.155 Uiso 0.50(2) 1 calc GR . P A 2
C8A C 0.7009(14) 0.3789(15) 0.412(3) 0.104(8) Uani 0.50(2) 1 d . U P A 2
H8AA H 0.674991 0.380240 0.325332 0.156 Uiso 0.50(2) 1 calc GR . P A 2
H8AB H 0.690352 0.324059 0.452920 0.156 Uiso 0.50(2) 1 calc GR . P A 2
H8AC H 0.761651 0.387817 0.404133 0.156 Uiso 0.50(2) 1 calc GR . P A 2
C13 C 0.3992(11) 0.2912(13) 0.455(3) 0.060(4) Uani 0.50(2) 1 d . U P B 1
H13A H 0.395497 0.285674 0.358506 0.072 Uiso 0.50(2) 1 calc R . P B 1
H13B H 0.378053 0.238562 0.494800 0.072 Uiso 0.50(2) 1 calc R . P B 1
C15 C 0.5511(15) 0.2650(13) 0.398(3) 0.059(4) Uani 0.50(2) 1 d . U P B 1
H15A H 0.610381 0.267757 0.423547 0.089 Uiso 0.50(2) 1 calc GR . P B 1
H15B H 0.543631 0.293181 0.313278 0.089 Uiso 0.50(2) 1 calc GR . P B 1
H15C H 0.533816 0.206049 0.390051 0.089 Uiso 0.50(2) 1 calc GR . P B 1
C16 C 0.5112(19) 0.2768(12) 0.6317(18) 0.070(6) Uani 0.50(2) 1 d . U P B 1
H16A H 0.494480 0.217548 0.636339 0.105 Uiso 0.50(2) 1 calc GR . P B 1
H16B H 0.477229 0.309716 0.693135 0.105 Uiso 0.50(2) 1 calc GR . P B 1
H16C H 0.570836 0.282085 0.654667 0.105 Uiso 0.50(2) 1 calc GR . P B 1
C13A C 0.4096(11) 0.2863(10) 0.547(3) 0.050(4) Uani 0.50(2) 1 d . U P B 2
H13C H 0.408692 0.280882 0.642993 0.060 Uiso 0.50(2) 1 calc R . P B 2
H13D H 0.390636 0.232544 0.507735 0.060 Uiso 0.50(2) 1 calc R . P B 2
C15A C 0.5175(18) 0.2754(14) 0.3538(19) 0.061(5) Uani 0.50(2) 1 d . U P B 2
H15D H 0.474101 0.296246 0.293943 0.091 Uiso 0.50(2) 1 calc GR . P B 2
H15E H 0.517694 0.213803 0.352773 0.091 Uiso 0.50(2) 1 calc GR . P B 2
H15F H 0.572670 0.296327 0.325932 0.091 Uiso 0.50(2) 1 calc GR . P B 2
C16A C 0.5621(15) 0.2626(12) 0.604(2) 0.065(6) Uani 0.50(2) 1 d . U P B 2
H16D H 0.620326 0.270387 0.574565 0.098 Uiso 0.50(2) 1 calc GR . P B 2
H16E H 0.549369 0.202364 0.608313 0.098 Uiso 0.50(2) 1 calc GR . P B 2
H16F H 0.554860 0.287905 0.690278 0.098 Uiso 0.50(2) 1 calc GR . P B 2
C3 C 0.3885(10) 0.5240(8) 0.5202(18) 0.037(3) Uani 0.512(14) 1 d D U P C 1
H3 H 0.390157 0.533928 0.616780 0.045 Uiso 0.512(14) 1 calc R . P C 1
C4 C 0.4589(9) 0.5798(9) 0.4613(18) 0.033(2) Uani 0.512(14) 1 d D U P C 1
H4 H 0.453913 0.581424 0.363809 0.039 Uiso 0.512(14) 1 calc R . P C 1
C22 C 0.4467(10) 0.6710(11) 0.5197(19) 0.040(3) Uani 0.512(14) 1 d D U P C 1
H22A H 0.472158 0.671434 0.608077 0.048 Uiso 0.512(14) 1 calc R . P C 1
H22B H 0.479724 0.710391 0.465163 0.048 Uiso 0.512(14) 1 calc R . P C 1
C21 C 0.3598(9) 0.7057(9) 0.5315(19) 0.050(3) Uani 0.512(14) 1 d D U P C 1
H21A H 0.357908 0.760222 0.484906 0.060 Uiso 0.512(14) 1 calc R . P C 1
H21B H 0.348511 0.717081 0.625040 0.060 Uiso 0.512(14) 1 calc R . P C 1
C20 C 0.2884(12) 0.6494(11) 0.4781(19) 0.051(3) Uani 0.512(14) 1 d D U P C 1
H20A H 0.237653 0.659918 0.531783 0.061 Uiso 0.512(14) 1 calc R . P C 1
H20B H 0.275420 0.668476 0.388150 0.061 Uiso 0.512(14) 1 calc R . P C 1
C19 C 0.3021(9) 0.5570(11) 0.473(2) 0.044(3) Uani 0.512(14) 1 d D U P C 1
H19A H 0.293658 0.538206 0.382107 0.053 Uiso 0.512(14) 1 calc R . P C 1
H19B H 0.257949 0.529922 0.527219 0.053 Uiso 0.512(14) 1 calc R . P C 1
C3A C 0.3978(10) 0.5254(8) 0.4791(18) 0.035(3) Uani 0.488(14) 1 d D U P C 2
H3A H 0.395866 0.533689 0.382223 0.042 Uiso 0.488(14) 1 calc R . P C 2
C4A C 0.4655(9) 0.5868(9) 0.5316(19) 0.033(2) Uani 0.488(14) 1 d D U P C 2
H4A H 0.460473 0.586090 0.629032 0.040 Uiso 0.488(14) 1 calc R . P C 2
C22A C 0.4404(11) 0.6785(10) 0.486(2) 0.037(3) Uani 0.488(14) 1 d D U P C 2
H22C H 0.457059 0.717040 0.557922 0.045 Uiso 0.488(14) 1 calc R . P C 2
H22D H 0.476407 0.692354 0.410524 0.045 Uiso 0.488(14) 1 calc R . P C 2
C21A C 0.3518(9) 0.7014(10) 0.449(2) 0.050(3) Uani 0.488(14) 1 d D U P C 2
H21C H 0.345449 0.697892 0.352990 0.060 Uiso 0.488(14) 1 calc R . P C 2
H21D H 0.340101 0.760097 0.476033 0.060 Uiso 0.488(14) 1 calc R . P C 2
C20A C 0.2873(12) 0.6408(11) 0.516(2) 0.049(3) Uani 0.488(14) 1 d D U P C 2
H20C H 0.275352 0.663596 0.604592 0.059 Uiso 0.488(14) 1 calc R . P C 2
H20D H 0.234136 0.643822 0.466123 0.059 Uiso 0.488(14) 1 calc R . P C 2
C19A C 0.3091(11) 0.5503(12) 0.532(2) 0.045(3) Uani 0.488(14) 1 d D U P C 2
H19C H 0.266237 0.516199 0.486006 0.054 Uiso 0.488(14) 1 calc R . P C 2
H19D H 0.306293 0.535799 0.625976 0.054 Uiso 0.488(14) 1 calc R . P C 2
Sb1 Sb 0.50457(2) 0.97309(2) 0.49983(7) 0.04663(14) Uani 1 1 d D . . . .
F1 F 0.5696(10) 0.8834(9) 0.5681(16) 0.110(4) Uani 0.392(8) 1 d D U P D 1
F2 F 0.4411(9) 1.0647(9) 0.4377(17) 0.119(4) Uani 0.392(8) 1 d D U P D 1
F3 F 0.4375(10) 0.9004(10) 0.4044(16) 0.118(4) Uani 0.392(8) 1 d D U P D 1
F4 F 0.4294(10) 0.9612(13) 0.6424(14) 0.129(4) Uani 0.392(8) 1 d D U P D 1
F5 F 0.5703(10) 1.0483(11) 0.6062(17) 0.127(5) Uani 0.392(8) 1 d D U P D 1
F6 F 0.5857(9) 0.9884(12) 0.3678(14) 0.116(4) Uani 0.392(8) 1 d D U P D 1
F1' F 0.5619(9) 0.8766(8) 0.4408(16) 0.108(4) Uani 0.426(6) 1 d D U P D 2
F2' F 0.4427(9) 1.0694(8) 0.5521(16) 0.111(4) Uani 0.426(6) 1 d D U P D 2
F3' F 0.4402(11) 0.9730(12) 0.3391(14) 0.139(4) Uani 0.426(6) 1 d D U P D 2
F4' F 0.4105(7) 0.9059(8) 0.5459(17) 0.115(4) Uani 0.426(6) 1 d D U P D 2
F5' F 0.5580(12) 0.9672(11) 0.6579(13) 0.142(4) Uani 0.426(6) 1 d D U P D 2
F6' F 0.5890(9) 1.0419(10) 0.424(2) 0.124(4) Uani 0.426(6) 1 d D U P D 2
F1'' F 0.6065(9) 1.0244(13) 0.559(2) 0.074(5) Uani 0.182(2) 1 d D U P D 3
F2'' F 0.4053(11) 0.9250(15) 0.438(2) 0.093(5) Uani 0.182(2) 1 d D U P D 3
F3'' F 0.5670(13) 0.9135(18) 0.371(2) 0.086(6) Uani 0.182(2) 1 d D U P D 3
F4'' F 0.5124(14) 0.8926(13) 0.634(2) 0.077(5) Uani 0.182(2) 1 d D U P D 3
F5'' F 0.4463(13) 1.0376(17) 0.624(2) 0.078(6) Uani 0.182(2) 1 d D U P D 3
F6'' F 0.4991(15) 1.0562(15) 0.368(2) 0.084(5) Uani 0.182(2) 1 d D U P D 3


_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
N1 C1 1.364(4) . ?
N1 C5 1.501(4) . ?
N1 C4 1.505(15) . ?
N1 C4A 1.426(16) . ?
N2 C2 1.353(4) . ?
N2 C12 1.501(4) . ?
N2 C3 1.462(12) . ?
N2 C3A 1.454(12) . ?
C1 C7 1.534(4) . ?
C1 C2 1.397(5) . ?
C7 C6 1.59(2) . ?
C7 C9 1.54(2) . ?
C7 C8 1.543(18) . ?
C7 C6A 1.50(2) . ?
C7 C9A 1.48(2) . ?
C7 C8A 1.55(2) . ?
C5 C11 1.486(12) . ?
C5 C10 1.545(10) . ?
C5 C6 1.54(2) . ?
C5 C6A 1.59(2) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C2 C14 1.541(5) . ?
C14 C13 1.622(18) . ?
C14 C15 1.47(2) . ?
C14 C16 1.428(17) . ?
C14 C13A 1.493(18) . ?
C14 C15A 1.57(2) . ?
C14 C16A 1.610(18) . ?
C12 C18 1.534(12) . ?
C12 C17 1.499(13) . ?
C12 C13 1.45(2) . ?
C12 C13A 1.606(17) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C6A H6AA 0.9700 . ?
C6A H6AB 0.9700 . ?
C9A H9AA 0.9600 . ?
C9A H9AB 0.9600 . ?
C9A H9AC 0.9600 . ?
C8A H8AA 0.9600 . ?
C8A H8AB 0.9600 . ?
C8A H8AC 0.9600 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C13A H13C 0.9700 . ?
C13A H13D 0.9700 . ?
C15A H15D 0.9600 . ?
C15A H15E 0.9600 . ?
C15A H15F 0.9600 . ?
C16A H16D 0.9600 . ?
C16A H16E 0.9600 . ?
C16A H16F 0.9600 . ?
C3 H3 0.9800 . ?
C3 C4 1.519(14) . ?
C3 C19 1.515(14) . ?
C4 H4 0.9800 . ?
C4 C22 1.548(15) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C21 1.461(14) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C20 1.514(14) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C19 1.455(14) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C3A H3A 0.9800 . ?
C3A C4A 1.518(14) . ?
C3A C19A 1.529(15) . ?
C4A H4A 0.9800 . ?
C4A C22A 1.548(14) . ?
C22A H22C 0.9700 . ?
C22A H22D 0.9700 . ?
C22A C21A 1.472(14) . ?
C21A H21C 0.9700 . ?
C21A H21D 0.9700 . ?
C21A C20A 1.535(15) . ?
C20A H20C 0.9700 . ?
C20A H20D 0.9700 . ?
C20A C19A 1.459(15) . ?
C19A H19C 0.9700 . ?
C19A H19D 0.9700 . ?
Sb1 F1 1.856(10) . ?
Sb1 F2 1.844(11) . ?
Sb1 F3 1.813(10) . ?
Sb1 F4 1.855(10) . ?
Sb1 F6 1.845(10) . ?
Sb1 F1' 1.845(9) . ?
Sb1 F2' 1.858(9) . ?
Sb1 F5' 1.791(11) . ?
Sb1 F2'' 1.827(14) . ?
Sb1 F4'' 1.842(13) . ?
Sb1 F5'' 1.836(12) . ?
Sb1 F6'' 1.851(13) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 114.1(3) . . ?
C1 N1 C4 117.3(7) . . ?
C1 N1 C4A 123.2(7) . . ?
C5 N1 C4 125.6(6) . . ?
C4A N1 C5 121.2(6) . . ?
C2 N2 C12 114.2(3) . . ?
C2 N2 C3 123.9(6) . . ?
C2 N2 C3A 117.9(7) . . ?
C3 N2 C12 121.4(6) . . ?
C3A N2 C12 126.9(6) . . ?
N1 C1 C7 109.5(3) . . ?
N1 C1 C2 119.9(3) . . ?
C2 C1 C7 130.5(3) . . ?
C1 C7 C6 102.5(8) . . ?
C1 C7 C9 118.0(9) . . ?
C1 C7 C8 111.3(9) . . ?
C1 C7 C8A 120.2(12) . . ?
C9 C7 C6 107.3(13) . . ?
C9 C7 C8 110.1(11) . . ?
C8 C7 C6 106.7(13) . . ?
C6A C7 C1 100.5(8) . . ?
C6A C7 C8A 108.3(12) . . ?
C9A C7 C1 106.1(13) . . ?
C9A C7 C6A 113.3(13) . . ?
C9A C7 C8A 108.5(13) . . ?
N1 C5 C10 112.4(7) . . ?
N1 C5 C6 102.7(8) . . ?
N1 C5 C6A 97.5(7) . . ?
C11 C5 N1 112.8(7) . . ?
C11 C5 C10 109.4(4) . . ?
C11 C5 C6 121.0(12) . . ?
C11 C5 C6A 94.9(11) . . ?
C10 C5 C6A 128.5(11) . . ?
C6 C5 C10 97.5(12) . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C2 C1 120.8(3) . . ?
N2 C2 C14 109.5(3) . . ?
C1 C2 C14 129.7(3) . . ?
C2 C14 C13 98.3(8) . . ?
C2 C14 C15A 108.9(10) . . ?
C2 C14 C16A 116.9(9) . . ?
C15 C14 C2 117.6(10) . . ?
C15 C14 C13 105.5(13) . . ?
C16 C14 C2 110.2(10) . . ?
C16 C14 C13 109.8(14) . . ?
C16 C14 C15 113.9(12) . . ?
C13A C14 C2 102.2(7) . . ?
C13A C14 C15A 113.5(13) . . ?
C13A C14 C16A 105.4(13) . . ?
C15A C14 C16A 109.8(11) . . ?
N2 C12 C18 112.4(8) . . ?
N2 C12 C13A 98.4(7) . . ?
C18 C12 C13A 126.7(12) . . ?
C17 C12 N2 112.5(8) . . ?
C17 C12 C18 109.8(4) . . ?
C17 C12 C13A 95.9(11) . . ?
C13 C12 N2 101.8(8) . . ?
C13 C12 C18 94.4(12) . . ?
C13 C12 C17 124.6(13) . . ?
C12 C18 H18A 109.5 . . ?
C12 C18 H18B 109.5 . . ?
C12 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C7 C6 H6A 110.6 . . ?
C7 C6 H6B 110.6 . . ?
C5 C6 C7 105.6(13) . . ?
C5 C6 H6A 110.6 . . ?
C5 C6 H6B 110.6 . . ?
H6A C6 H6B 108.7 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C6A C5 107.5(11) . . ?
C7 C6A H6AA 110.2 . . ?
C7 C6A H6AB 110.2 . . ?
C5 C6A H6AA 110.2 . . ?
C5 C6A H6AB 110.2 . . ?
H6AA C6A H6AB 108.5 . . ?
C7 C9A H9AA 109.5 . . ?
C7 C9A H9AB 109.5 . . ?
C7 C9A H9AC 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?
C7 C8A H8AA 109.5 . . ?
C7 C8A H8AB 109.5 . . ?
C7 C8A H8AC 109.5 . . ?
H8AA C8A H8AB 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 109.5 . . ?
C14 C13 H13A 110.1 . . ?
C14 C13 H13B 110.1 . . ?
C12 C13 C14 107.8(12) . . ?
C12 C13 H13A 110.1 . . ?
C12 C13 H13B 110.1 . . ?
H13A C13 H13B 108.5 . . ?
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 C13A C12 106.5(10) . . ?
C14 C13A H13C 110.4 . . ?
C14 C13A H13D 110.4 . . ?
C12 C13A H13C 110.4 . . ?
C12 C13A H13D 110.4 . . ?
H13C C13A H13D 108.6 . . ?
C14 C15A H15D 109.5 . . ?
C14 C15A H15E 109.5 . . ?
C14 C15A H15F 109.5 . . ?
H15D C15A H15E 109.5 . . ?
H15D C15A H15F 109.5 . . ?
H15E C15A H15F 109.5 . . ?
C14 C16A H16D 109.5 . . ?
C14 C16A H16E 109.5 . . ?
C14 C16A H16F 109.5 . . ?
H16D C16A H16E 109.5 . . ?
H16D C16A H16F 109.5 . . ?
H16E C16A H16F 109.5 . . ?
N2 C3 H3 106.0 . . ?
N2 C3 C4 107.5(11) . . ?
N2 C3 C19 121.4(13) . . ?
C4 C3 H3 106.0 . . ?
C19 C3 H3 106.0 . . ?
C19 C3 C4 109.0(13) . . ?
N1 C4 C3 113.1(12) . . ?
N1 C4 H4 110.1 . . ?
N1 C4 C22 106.4(13) . . ?
C3 C4 H4 110.1 . . ?
C3 C4 C22 106.8(12) . . ?
C22 C4 H4 110.1 . . ?
C4 C22 H22A 107.6 . . ?
C4 C22 H22B 107.6 . . ?
H22A C22 H22B 107.0 . . ?
C21 C22 C4 119.0(12) . . ?
C21 C22 H22A 107.6 . . ?
C21 C22 H22B 107.6 . . ?
C22 C21 H21A 108.3 . . ?
C22 C21 H21B 108.3 . . ?
C22 C21 C20 115.9(12) . . ?
H21A C21 H21B 107.4 . . ?
C20 C21 H21A 108.3 . . ?
C20 C21 H21B 108.3 . . ?
C21 C20 H20A 107.7 . . ?
C21 C20 H20B 107.7 . . ?
H20A C20 H20B 107.1 . . ?
C19 C20 C21 118.4(13) . . ?
C19 C20 H20A 107.7 . . ?
C19 C20 H20B 107.7 . . ?
C3 C19 H19A 108.0 . . ?
C3 C19 H19B 108.0 . . ?
C20 C19 C3 117.1(12) . . ?
C20 C19 H19A 108.0 . . ?
C20 C19 H19B 108.0 . . ?
H19A C19 H19B 107.3 . . ?
N2 C3A H3A 106.4 . . ?
N2 C3A C4A 116.4(11) . . ?
N2 C3A C19A 110.4(13) . . ?
C4A C3A H3A 106.4 . . ?
C4A C3A C19A 110.3(13) . . ?
C19A C3A H3A 106.4 . . ?
N1 C4A C3A 107.8(12) . . ?
N1 C4A H4A 106.3 . . ?
N1 C4A C22A 121.4(14) . . ?
C3A C4A H4A 106.3 . . ?
C3A C4A C22A 107.7(12) . . ?
C22A C4A H4A 106.3 . . ?
C4A C22A H22C 106.7 . . ?
C4A C22A H22D 106.7 . . ?
H22C C22A H22D 106.6 . . ?
C21A C22A C4A 122.4(13) . . ?
C21A C22A H22C 106.7 . . ?
C21A C22A H22D 106.7 . . ?
C22A C21A H21C 109.5 . . ?
C22A C21A H21D 109.5 . . ?
C22A C21A C20A 110.6(13) . . ?
H21C C21A H21D 108.1 . . ?
C20A C21A H21C 109.5 . . ?
C20A C21A H21D 109.5 . . ?
C21A C20A H20C 107.5 . . ?
C21A C20A H20D 107.5 . . ?
H20C C20A H20D 107.0 . . ?
C19A C20A C21A 119.3(13) . . ?
C19A C20A H20C 107.5 . . ?
C19A C20A H20D 107.5 . . ?
C3A C19A H19C 108.6 . . ?
C3A C19A H19D 108.6 . . ?
C20A C19A C3A 114.8(13) . . ?
C20A C19A H19C 108.6 . . ?
C20A C19A H19D 108.6 . . ?
H19C C19A H19D 107.5 . . ?
F2 Sb1 F1 177.8(7) . . ?
F2 Sb1 F4 90.0(6) . . ?
F2 Sb1 F6 91.4(6) . . ?
F3 Sb1 F1 92.2(7) . . ?
F3 Sb1 F2 89.8(6) . . ?
F3 Sb1 F4 88.9(9) . . ?
F3 Sb1 F6 95.5(8) . . ?
F4 Sb1 F1 89.2(6) . . ?
F6 Sb1 F1 89.3(6) . . ?
F6 Sb1 F4 175.3(8) . . ?
F1' Sb1 F2' 177.0(7) . . ?
F5' Sb1 F1' 91.0(6) . . ?
F5' Sb1 F2' 91.9(6) . . ?
F2'' Sb1 F4'' 91.5(7) . . ?
F2'' Sb1 F5'' 92.1(7) . . ?
F2'' Sb1 F6'' 90.3(8) . . ?
F4'' Sb1 F6'' 178.1(9) . . ?
F5'' Sb1 F4'' 85.0(13) . . ?
F5'' Sb1 F6'' 94.4(13) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.50(6)
2 0.50(6)

####################################################################### 
# 
# 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_AJ0759
_audit_block_doi                 10.5517/ccdc.csd.cc245s04
_database_code_depnum_ccdc_archive 'CCDC 1971755'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D0CC07385G 2021
loop_
_audit_author_name
_audit_author_address
'HEMANT RAWAT'
;TATA INSTITUTE OF FUNDAMENTAL RESEARCH HYDERABAD
India
;
_audit_update_record             
;
2020-05-21 deposited with the CCDC.	2021-05-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H40 N2, 2(C F3 O3 S)'
_chemical_formula_sum            'C24 H40 F6 N2 O6 S2'
_chemical_formula_weight         630.70

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   11.2936(4)
_cell_length_b                   16.1144(4)
_cell_length_c                   16.1904(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.094(3)
_cell_angle_gamma                90
_cell_volume                     2945.95(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    120.00(10)
_cell_measurement_reflns_used    12974
_cell_measurement_theta_min      3.1070
_cell_measurement_theta_max      28.9700

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_F_000             1328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    0.259
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.93748
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120.00(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26173
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.516
_diffrn_reflns_theta_max         29.029
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.881
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.881
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.881
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6921
_reflns_number_gt                5932
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0505P)²+1.8269P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0030(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6921
_refine_ls_number_parameters     370
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1091
_refine_ls_wR_factor_gt          0.1050
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.36891(10) 0.62970(7) 0.33000(7) 0.0128(2) Uani 1 1 d . . . . .
N2 N 0.10282(10) 0.60412(8) 0.30661(7) 0.0134(2) Uani 1 1 d . . . . .
C1 C 0.39006(13) 0.70719(9) 0.32060(9) 0.0161(3) Uani 1 1 d . . . . .
H1 H 0.350105 0.748240 0.349288 0.019 Uiso 1 1 calc R U . . .
C2 C 0.48374(13) 0.72620(9) 0.26006(9) 0.0178(3) Uani 1 1 d . . . . .
C3 C 0.50487(14) 0.64013(10) 0.22089(10) 0.0196(3) Uani 1 1 d . . . . .
H3A H 0.589084 0.629679 0.216350 0.024 Uiso 1 1 calc R U . . .
H3B H 0.468909 0.637716 0.166056 0.024 Uiso 1 1 calc R U . . .
C4 C 0.44799(13) 0.57483(9) 0.27774(9) 0.0156(3) Uani 1 1 d . . . . .
C5 C 0.53723(14) 0.53183(10) 0.33524(10) 0.0203(3) Uani 1 1 d . . . . .
H5A H 0.580354 0.572784 0.366620 0.030 Uiso 1 1 calc R U . . .
H5B H 0.591379 0.499883 0.303115 0.030 Uiso 1 1 calc R U . . .
H5C H 0.496108 0.495748 0.372158 0.030 Uiso 1 1 calc R U . . .
C6 C 0.37339(14) 0.51214(10) 0.22968(10) 0.0210(3) Uani 1 1 d . . . . .
H6A H 0.337166 0.474398 0.267493 0.032 Uiso 1 1 calc R U . . .
H6B H 0.422939 0.481725 0.192846 0.032 Uiso 1 1 calc R U . . .
H6C H 0.312969 0.540695 0.198347 0.032 Uiso 1 1 calc R U . . .
C7 C 0.59131(15) 0.76044(11) 0.30944(11) 0.0254(3) Uani 1 1 d . . . . .
H7A H 0.567592 0.808135 0.340564 0.038 Uiso 1 1 calc R U . . .
H7B H 0.652315 0.776003 0.271969 0.038 Uiso 1 1 calc R U . . .
H7C H 0.620926 0.718469 0.346498 0.038 Uiso 1 1 calc R U . . .
C8 C 0.43967(15) 0.79112(10) 0.19760(11) 0.0244(3) Uani 1 1 d . . . . .
H8A H 0.373401 0.769189 0.166662 0.037 Uiso 1 1 calc R U . . .
H8B H 0.502214 0.804630 0.160590 0.037 Uiso 1 1 calc R U . . .
H8C H 0.415764 0.840238 0.226403 0.037 Uiso 1 1 calc R U . . .
C9 C 0.28936(12) 0.59617(9) 0.39458(8) 0.0134(3) Uani 1 1 d . . . . .
H9 H 0.286332 0.535617 0.389291 0.016 Uiso 1 1 calc R U . . .
C10 C 0.16277(13) 0.63061(9) 0.38515(8) 0.0134(3) Uani 1 1 d . . . . .
H10 H 0.166436 0.691364 0.386248 0.016 Uiso 1 1 calc R U . . .
C11 C 0.08591(13) 0.60111(10) 0.45671(9) 0.0180(3) Uani 1 1 d . . . . .
H11A H 0.006995 0.624339 0.450558 0.022 Uiso 1 1 calc R U . . .
H11B H 0.079171 0.541119 0.455185 0.022 Uiso 1 1 calc R U . . .
C12 C 0.14005(15) 0.62780(10) 0.53922(9) 0.0211(3) Uani 1 1 d . . . . .
H12A H 0.090076 0.609533 0.583767 0.025 Uiso 1 1 calc R U . . .
H12B H 0.145354 0.687846 0.541385 0.025 Uiso 1 1 calc R U . . .
C13 C 0.26296(14) 0.59022(10) 0.54989(9) 0.0191(3) Uani 1 1 d . . . . .
H13A H 0.257078 0.530171 0.549876 0.023 Uiso 1 1 calc R U . . .
H13B H 0.297291 0.607387 0.602537 0.023 Uiso 1 1 calc R U . . .
C14 C 0.34290(14) 0.61813(9) 0.48000(9) 0.0169(3) Uani 1 1 d . . . . .
H14A H 0.419651 0.591653 0.486437 0.020 Uiso 1 1 calc R U . . .
H14B H 0.354632 0.677672 0.483461 0.020 Uiso 1 1 calc R U . . .
C15 C 0.08753(13) 0.52842(9) 0.28590(9) 0.0169(3) Uani 1 1 d . . . . .
H15 H 0.124407 0.484688 0.313666 0.020 Uiso 1 1 calc R U . . .
C16 C 0.00586(14) 0.51572(10) 0.21368(9) 0.0199(3) Uani 1 1 d . . . . .
C17 C -0.01054(14) 0.60560(10) 0.18225(9) 0.0195(3) Uani 1 1 d . . . . .
H17A H -0.093497 0.616349 0.169827 0.023 Uiso 1 1 calc R U . . .
H17B H 0.034046 0.614041 0.132331 0.023 Uiso 1 1 calc R U . . .
C18 C 0.03484(13) 0.66474(9) 0.25125(9) 0.0161(3) Uani 1 1 d . . . . .
C19 C 0.11887(15) 0.73012(10) 0.21917(10) 0.0210(3) Uani 1 1 d . . . . .
H19A H 0.148923 0.762771 0.264520 0.032 Uiso 1 1 calc R U . . .
H19B H 0.077349 0.765431 0.180640 0.032 Uiso 1 1 calc R U . . .
H19C H 0.183524 0.703557 0.192044 0.032 Uiso 1 1 calc R U . . .
C20 C -0.06389(15) 0.70460(11) 0.30076(10) 0.0254(4) Uani 1 1 d . . . . .
H20A H -0.115095 0.662131 0.321375 0.038 Uiso 1 1 calc R U . . .
H20B H -0.108721 0.741579 0.265755 0.038 Uiso 1 1 calc R U . . .
H20C H -0.029912 0.735151 0.346264 0.038 Uiso 1 1 calc R U . . .
C21 C 0.05837(17) 0.45720(11) 0.14977(11) 0.0291(4) Uani 1 1 d . . . . .
H21A H 0.129165 0.481260 0.128241 0.044 Uiso 1 1 calc R U . . .
H21B H 0.001900 0.448612 0.105528 0.044 Uiso 1 1 calc R U . . .
H21C H 0.077047 0.404974 0.175394 0.044 Uiso 1 1 calc R U . . .
C22 C -0.10849(17) 0.47821(12) 0.24899(11) 0.0315(4) Uani 1 1 d . . . . .
H22A H -0.090803 0.425518 0.273991 0.047 Uiso 1 1 calc R U . . .
H22B H -0.165953 0.470760 0.205161 0.047 Uiso 1 1 calc R U . . .
H22C H -0.139747 0.515049 0.289762 0.047 Uiso 1 1 calc R U . . .
S1 S 0.75418(4) 0.85955(2) 0.03997(3) 0.02066(11) Uani 1 1 d . . . . .
F1 F 0.73774(10) 0.72189(7) 0.12567(7) 0.0392(3) Uani 1 1 d . . . . .
F2 F 0.66832(15) 0.71406(8) 0.00318(9) 0.0673(5) Uani 1 1 d . . . . .
F3 F 0.85692(13) 0.71597(8) 0.02485(8) 0.0552(4) Uani 1 1 d . . . . .
O1 O 0.77794(12) 0.87379(8) -0.04569(8) 0.0298(3) Uani 1 1 d . . . . .
O2 O 0.84907(14) 0.88333(10) 0.09551(9) 0.0465(4) Uani 1 1 d . . . . .
O3 O 0.63905(13) 0.88441(9) 0.06609(10) 0.0456(4) Uani 1 1 d . . . . .
C23 C 0.75451(16) 0.74700(10) 0.04789(10) 0.0258(4) Uani 1 1 d . . . . .
S2 S 0.71294(4) 0.36890(2) 0.01758(2) 0.02190(11) Uani 1 1 d . . . . .
F4 F 0.63346(12) 0.48973(8) 0.10951(7) 0.0456(3) Uani 1 1 d . . . . .
F5 F 0.62630(11) 0.51474(7) -0.02107(7) 0.0393(3) Uani 1 1 d . . . . .
F6 F 0.79270(11) 0.51918(7) 0.04584(7) 0.0397(3) Uani 1 1 d . . . . .
O4 O 0.76823(15) 0.36957(9) -0.06105(9) 0.0437(4) Uani 1 1 d . . . . .
O5 O 0.78501(12) 0.34052(8) 0.08679(8) 0.0298(3) Uani 1 1 d . . . . .
O6 O 0.59459(13) 0.33520(9) 0.01690(10) 0.0435(4) Uani 1 1 d . . . . .
C24 C 0.68910(16) 0.47885(11) 0.03890(10) 0.0255(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.2810(19) . ?
N1 C9 1.4927(18) . ?
N1 C4 1.5246(18) . ?
N2 C15 1.276(2) . ?
N2 C10 1.4915(18) . ?
N2 C18 1.5234(18) . ?
C1 C2 1.488(2) . ?
C1 H1 0.9300 . ?
C2 C8 1.531(2) . ?
C2 C7 1.544(2) . ?
C2 C3 1.546(2) . ?
C3 C4 1.546(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C6 1.520(2) . ?
C4 C5 1.525(2) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.539(2) . ?
C9 C14 1.5400(19) . ?
C9 H9 0.9800 . ?
C10 C11 1.5363(19) . ?
C10 H10 0.9800 . ?
C11 C12 1.521(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.521(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.529(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.490(2) . ?
C15 H15 0.9300 . ?
C16 C21 1.528(2) . ?
C16 C17 1.545(2) . ?
C16 C22 1.545(2) . ?
C17 C18 1.548(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.516(2) . ?
C18 C20 1.527(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
S1 O3 1.4321(14) . ?
S1 O1 1.4360(13) . ?
S1 O2 1.4377(15) . ?
S1 C23 1.8183(17) . ?
F1 C23 1.339(2) . ?
F2 C23 1.314(2) . ?
F3 C23 1.320(2) . ?
S2 O4 1.4286(14) . ?
S2 O6 1.4426(15) . ?
S2 O5 1.4466(13) . ?
S2 C24 1.8259(17) . ?
F4 C24 1.327(2) . ?
F5 C24 1.3243(19) . ?
F6 C24 1.341(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C9 123.52(12) . . ?
C1 N1 C4 112.76(12) . . ?
C9 N1 C4 123.06(11) . . ?
C15 N2 C10 123.68(12) . . ?
C15 N2 C18 113.22(12) . . ?
C10 N2 C18 122.24(11) . . ?
N1 C1 C2 114.55(13) . . ?
N1 C1 H1 122.7 . . ?
C2 C1 H1 122.7 . . ?
C1 C2 C8 110.45(13) . . ?
C1 C2 C7 107.15(13) . . ?
C8 C2 C7 109.91(13) . . ?
C1 C2 C3 101.71(12) . . ?
C8 C2 C3 113.14(13) . . ?
C7 C2 C3 114.02(13) . . ?
C2 C3 C4 107.30(12) . . ?
C2 C3 H3A 110.3 . . ?
C4 C3 H3A 110.3 . . ?
C2 C3 H3B 110.3 . . ?
C4 C3 H3B 110.3 . . ?
H3A C3 H3B 108.5 . . ?
C6 C4 N1 110.17(12) . . ?
C6 C4 C5 111.33(13) . . ?
N1 C4 C5 108.18(12) . . ?
C6 C4 C3 112.34(13) . . ?
N1 C4 C3 100.96(11) . . ?
C5 C4 C3 113.29(13) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C2 C8 H8A 109.5 . . ?
C2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 C10 111.74(11) . . ?
N1 C9 C14 108.33(11) . . ?
C10 C9 C14 110.75(12) . . ?
N1 C9 H9 108.6 . . ?
C10 C9 H9 108.6 . . ?
C14 C9 H9 108.6 . . ?
N2 C10 C11 107.49(11) . . ?
N2 C10 C9 112.78(11) . . ?
C11 C10 C9 110.54(11) . . ?
N2 C10 H10 108.6 . . ?
C11 C10 H10 108.6 . . ?
C9 C10 H10 108.6 . . ?
C12 C11 C10 110.58(12) . . ?
C12 C11 H11A 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C11 C12 C13 109.75(13) . . ?
C11 C12 H12A 109.7 . . ?
C13 C12 H12A 109.7 . . ?
C11 C12 H12B 109.7 . . ?
C13 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
C12 C13 C14 110.45(12) . . ?
C12 C13 H13A 109.6 . . ?
C14 C13 H13A 109.6 . . ?
C12 C13 H13B 109.6 . . ?
C14 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C13 C14 C9 111.70(12) . . ?
C13 C14 H14A 109.3 . . ?
C9 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
C9 C14 H14B 109.3 . . ?
H14A C14 H14B 107.9 . . ?
N2 C15 C16 114.60(13) . . ?
N2 C15 H15 122.7 . . ?
C16 C15 H15 122.7 . . ?
C15 C16 C21 111.95(14) . . ?
C15 C16 C17 101.44(12) . . ?
C21 C16 C17 113.65(13) . . ?
C15 C16 C22 105.82(12) . . ?
C21 C16 C22 110.30(14) . . ?
C17 C16 C22 113.12(14) . . ?
C16 C17 C18 107.66(12) . . ?
C16 C17 H17A 110.2 . . ?
C18 C17 H17A 110.2 . . ?
C16 C17 H17B 110.2 . . ?
C18 C17 H17B 110.2 . . ?
H17A C17 H17B 108.5 . . ?
C19 C18 N2 109.60(12) . . ?
C19 C18 C20 110.82(14) . . ?
N2 C18 C20 109.00(12) . . ?
C19 C18 C17 112.42(12) . . ?
N2 C18 C17 100.72(11) . . ?
C20 C18 C17 113.74(13) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C16 C22 H22A 109.5 . . ?
C16 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C16 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 S1 O1 115.34(9) . . ?
O3 S1 O2 114.26(10) . . ?
O1 S1 O2 114.25(9) . . ?
O3 S1 C23 105.00(9) . . ?
O1 S1 C23 103.14(8) . . ?
O2 S1 C23 102.78(9) . . ?
F2 C23 F3 109.58(16) . . ?
F2 C23 F1 106.23(15) . . ?
F3 C23 F1 106.95(14) . . ?
F2 C23 S1 111.32(12) . . ?
F3 C23 S1 111.00(13) . . ?
F1 C23 S1 111.56(12) . . ?
O4 S2 O6 114.63(10) . . ?
O4 S2 O5 116.34(9) . . ?
O6 S2 O5 113.22(8) . . ?
O4 S2 C24 103.28(8) . . ?
O6 S2 C24 103.11(9) . . ?
O5 S2 C24 104.07(8) . . ?
F5 C24 F4 108.56(14) . . ?
F5 C24 F6 107.69(14) . . ?
F4 C24 F6 106.89(14) . . ?
F5 C24 S2 111.34(11) . . ?
F4 C24 S2 111.42(12) . . ?
F6 C24 S2 110.76(12) . . ?

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
C9 N1 C1 C2 172.37(12) . . . . ?
C4 N1 C1 C2 1.42(17) . . . . ?
N1 C1 C2 C8 129.33(14) . . . . ?
N1 C1 C2 C7 -110.97(15) . . . . ?
N1 C1 C2 C3 8.96(17) . . . . ?
C1 C2 C3 C4 -15.34(15) . . . . ?
C8 C2 C3 C4 -133.81(13) . . . . ?
C7 C2 C3 C4 99.62(15) . . . . ?
C1 N1 C4 C6 -130.00(13) . . . . ?
C9 N1 C4 C6 59.00(16) . . . . ?
C1 N1 C4 C5 108.09(14) . . . . ?
C9 N1 C4 C5 -62.90(16) . . . . ?
C1 N1 C4 C3 -11.08(15) . . . . ?
C9 N1 C4 C3 177.92(12) . . . . ?
C2 C3 C4 C6 133.24(13) . . . . ?
C2 C3 C4 N1 15.90(15) . . . . ?
C2 C3 C4 C5 -99.53(15) . . . . ?
C1 N1 C9 C10 59.50(17) . . . . ?
C4 N1 C9 C10 -130.47(13) . . . . ?
C1 N1 C9 C14 -62.78(17) . . . . ?
C4 N1 C9 C14 107.26(14) . . . . ?
C15 N2 C10 C11 -64.64(18) . . . . ?
C18 N2 C10 C11 104.07(14) . . . . ?
C15 N2 C10 C9 57.46(18) . . . . ?
C18 N2 C10 C9 -133.83(13) . . . . ?
N1 C9 C10 N2 64.59(15) . . . . ?
C14 C9 C10 N2 -174.53(11) . . . . ?
N1 C9 C10 C11 -175.05(11) . . . . ?
C14 C9 C10 C11 -54.17(15) . . . . ?
N2 C10 C11 C12 -178.62(12) . . . . ?
C9 C10 C11 C12 57.91(16) . . . . ?
C10 C11 C12 C13 -60.24(17) . . . . ?
C11 C12 C13 C14 59.18(16) . . . . ?
C12 C13 C14 C9 -56.43(16) . . . . ?
N1 C9 C14 C13 176.75(12) . . . . ?
C10 C9 C14 C13 53.87(16) . . . . ?
C10 N2 C15 C16 168.69(13) . . . . ?
C18 N2 C15 C16 -0.93(18) . . . . ?
N2 C15 C16 C21 131.61(15) . . . . ?
N2 C15 C16 C17 10.09(17) . . . . ?
N2 C15 C16 C22 -108.19(16) . . . . ?
C15 C16 C17 C18 -14.87(16) . . . . ?
C21 C16 C17 C18 -135.19(14) . . . . ?
C22 C16 C17 C18 98.02(15) . . . . ?
C15 N2 C18 C19 -127.29(14) . . . . ?
C10 N2 C18 C19 62.92(16) . . . . ?
C15 N2 C18 C20 111.26(15) . . . . ?
C10 N2 C18 C20 -58.53(17) . . . . ?
C15 N2 C18 C17 -8.64(16) . . . . ?
C10 N2 C18 C17 -178.43(12) . . . . ?
C16 C17 C18 C19 130.88(14) . . . . ?
C16 C17 C18 N2 14.31(15) . . . . ?
C16 C17 C18 C20 -102.14(15) . . . . ?
O3 S1 C23 F2 57.34(16) . . . . ?
O1 S1 C23 F2 -63.83(16) . . . . ?
O2 S1 C23 F2 177.13(15) . . . . ?
O3 S1 C23 F3 179.69(13) . . . . ?
O1 S1 C23 F3 58.52(14) . . . . ?
O2 S1 C23 F3 -60.51(14) . . . . ?
O3 S1 C23 F1 -61.14(15) . . . . ?
O1 S1 C23 F1 177.70(12) . . . . ?
O2 S1 C23 F1 58.66(14) . . . . ?
O4 S2 C24 F5 56.29(15) . . . . ?
O6 S2 C24 F5 -63.36(15) . . . . ?
O5 S2 C24 F5 178.23(12) . . . . ?
O4 S2 C24 F4 177.64(13) . . . . ?
O6 S2 C24 F4 58.00(14) . . . . ?
O5 S2 C24 F4 -60.42(14) . . . . ?
O4 S2 C24 F6 -63.51(14) . . . . ?
O6 S2 C24 F6 176.84(12) . . . . ?
O5 S2 C24 F6 58.43(13) . . . . ?

_refine_diff_density_max         0.660
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_AJ0121
_audit_block_doi                 10.5517/ccdc.csd.cc245s48
_database_code_depnum_ccdc_archive 'CCDC 1971759'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D0CC07385G 2021
loop_
_audit_author_name
_audit_author_address
'HEMANT RAWAT'
;TATA INSTITUTE OF FUNDAMENTAL RESEARCH HYDERABAD
India
;
_audit_update_record             
;
2020-05-21 deposited with the CCDC.	2021-05-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H36 N2, 2(C F3 O3 S)'
_chemical_formula_sum            'C21 H36 F6 N2 O6 S2'
_chemical_formula_weight         590.64

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.0062(6)
_cell_length_b                   12.0297(5)
_cell_length_c                   23.0723(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2777.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    10334
_cell_measurement_theta_min      3.1700
_cell_measurement_theta_max      28.6980

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_F_000             1240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.479
_exptl_crystal_size_mid          0.124
_exptl_crystal_size_min          0.104
_exptl_absorpt_coefficient_mu    0.269
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.23852
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30895
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.446
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             5416
_reflns_number_gt                4827
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.753
_reflns_Friedel_fraction_max     0.982
_reflns_Friedel_fraction_full    0.986

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0568P)²+1.2402P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1843 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5416
_refine_ls_number_parameters     488
_refine_ls_number_restraints     754
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1052
_refine_ls_wR_factor_gt          0.1019
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.3030(3) 0.1802(2) 0.31721(12) 0.0275(6) Uani 1 1 d . . . . .
N2 N 0.2858(3) 0.4797(2) 0.46439(11) 0.0246(6) Uani 1 1 d . . . . .
C1 C 0.3015(4) 0.2423(3) 0.27251(15) 0.0288(7) Uani 1 1 d . . . . .
H1 H 0.321151 0.319481 0.274102 0.035 Uiso 1 1 calc R U . . .
C2 C 0.2666(4) 0.1841(3) 0.21739(14) 0.0266(8) Uani 1 1 d . . . . .
C3 C 0.2727(4) 0.0612(3) 0.23676(14) 0.0336(8) Uani 1 1 d . . . . .
H3A H 0.195393 0.019775 0.220953 0.040 Uiso 1 1 calc R U . . .
H3B H 0.355719 0.026076 0.222264 0.040 Uiso 1 1 calc R U . . .
C4 C 0.2700(4) 0.0586(3) 0.30343(13) 0.0264(7) Uani 1 1 d . . . . .
C5 C 0.2878(3) 0.5605(3) 0.42887(14) 0.0275(8) Uani 1 1 d . . . . .
H5 H 0.302969 0.550743 0.388546 0.033 Uiso 1 1 calc R U . . .
C6 C 0.2649(4) 0.6711(3) 0.45522(14) 0.0276(7) Uani 1 1 d . . . . .
C7 C 0.2585(6) 0.6424(3) 0.51990(17) 0.0494(11) Uani 1 1 d . . . . .
H7A H 0.336446 0.674665 0.540274 0.059 Uiso 1 1 calc R U . . .
H7B H 0.176170 0.673819 0.537196 0.059 Uiso 1 1 calc R U . . .
C8 C 0.2588(4) 0.5157(3) 0.52645(13) 0.0243(7) Uani 1 1 d . . . . .
C9 C 0.3707(4) 0.2118(3) 0.17148(16) 0.0323(8) Uani 1 1 d . . . . .
H9A H 0.367847 0.291532 0.162967 0.048 Uiso 1 1 calc R U . . .
H9B H 0.351647 0.169648 0.136075 0.048 Uiso 1 1 calc R U . . .
H9C H 0.459761 0.191905 0.185854 0.048 Uiso 1 1 calc R U . . .
C10 C 0.1289(4) 0.2216(4) 0.19802(19) 0.0410(10) Uani 1 1 d . . . . .
H10A H 0.063102 0.202484 0.227850 0.062 Uiso 1 1 calc R U . . .
H10B H 0.105497 0.184371 0.161640 0.062 Uiso 1 1 calc R U . . .
H10C H 0.129229 0.302285 0.192061 0.062 Uiso 1 1 calc R U . . .
C11 C 0.1360(4) 0.0294(4) 0.32861(17) 0.0387(9) Uani 1 1 d . . . . .
H11A H 0.139875 0.035175 0.370948 0.058 Uiso 1 1 calc R U . . .
H11B H 0.112549 -0.046903 0.317663 0.058 Uiso 1 1 calc R U . . .
H11C H 0.068242 0.080690 0.313652 0.058 Uiso 1 1 calc R U . . .
C12 C 0.3801(4) -0.0130(3) 0.32865(16) 0.0333(8) Uani 1 1 d . . . . .
H12A H 0.466894 0.013302 0.314532 0.050 Uiso 1 1 calc R U . . .
H12B H 0.366812 -0.090383 0.316683 0.050 Uiso 1 1 calc R U . . .
H12C H 0.377845 -0.008259 0.371040 0.050 Uiso 1 1 calc R U . . .
C13 C 0.3291(4) 0.2145(3) 0.37754(15) 0.0351(9) Uani 1 1 d . . . . .
H13A H 0.421958 0.194360 0.387964 0.042 Uiso 1 1 calc R U . . .
H13B H 0.268274 0.173329 0.403726 0.042 Uiso 1 1 calc R U . . .
C14 C 0.3095(4) 0.3384(3) 0.38660(14) 0.0308(8) Uani 1 1 d . . . . .
H14A H 0.382352 0.380144 0.367386 0.037 Uiso 1 1 calc R U . . .
H14B H 0.223435 0.362220 0.369470 0.037 Uiso 1 1 calc R U . . .
C15 C 0.3102(4) 0.3620(3) 0.45116(14) 0.0289(8) Uani 1 1 d . . . . .
H15A H 0.240475 0.316271 0.470114 0.035 Uiso 1 1 calc R U . . .
H15B H 0.397728 0.339895 0.467467 0.035 Uiso 1 1 calc R U . . .
C16 C 0.3711(5) 0.4769(4) 0.56498(16) 0.0478(12) Uani 1 1 d . . . . .
H16A H 0.373760 0.395427 0.565196 0.072 Uiso 1 1 calc R U . . .
H16B H 0.356396 0.504088 0.604498 0.072 Uiso 1 1 calc R U . . .
H16C H 0.456134 0.505811 0.550283 0.072 Uiso 1 1 calc R U . . .
C17 C 0.1266(5) 0.4694(5) 0.5457(2) 0.0575(13) Uani 1 1 d . . . . .
H17A H 0.056794 0.492477 0.518407 0.086 Uiso 1 1 calc R U . . .
H17B H 0.105307 0.497471 0.584449 0.086 Uiso 1 1 calc R U . . .
H17C H 0.131489 0.388067 0.546657 0.086 Uiso 1 1 calc R U . . .
C18 C 0.3821(4) 0.7465(3) 0.4409(2) 0.0427(10) Uani 1 1 d . . . . .
H18A H 0.465641 0.710117 0.452377 0.064 Uiso 1 1 calc R U . . .
H18B H 0.372673 0.816814 0.461896 0.064 Uiso 1 1 calc R U . . .
H18C H 0.383608 0.761081 0.399093 0.064 Uiso 1 1 calc R U . . .
C19 C 0.1356(4) 0.7225(4) 0.4310(2) 0.0437(10) Uani 1 1 d . . . . .
H19A H 0.141904 0.727645 0.388695 0.066 Uiso 1 1 calc R U . . .
H19B H 0.123281 0.796945 0.447349 0.066 Uiso 1 1 calc R U . . .
H19C H 0.059321 0.675529 0.441515 0.066 Uiso 1 1 calc R U . . .
S1 S 0.74930(12) 0.04647(11) 0.24609(4) 0.0246(3) Uani 0.922(3) 1 d D U P A 1
O1 O 0.8727(3) 0.0356(3) 0.21575(18) 0.0535(9) Uani 0.922(3) 1 d D U P A 1
O2 O 0.6328(3) 0.0403(3) 0.20995(13) 0.0405(8) Uani 0.922(3) 1 d D U P A 1
O3 O 0.7376(4) -0.0174(2) 0.29814(13) 0.0485(9) Uani 0.922(3) 1 d D U P A 1
F1 F 0.7635(4) 0.2588(2) 0.22939(16) 0.0796(11) Uani 0.922(3) 1 d D U P A 1
F2 F 0.8496(3) 0.2055(3) 0.30886(16) 0.0498(9) Uani 0.922(3) 1 d D U P A 1
F3 F 0.6357(3) 0.2129(3) 0.29962(16) 0.0623(10) Uani 0.922(3) 1 d D U P A 1
C20 C 0.7489(5) 0.1875(3) 0.2729(2) 0.0357(10) Uani 0.922(3) 1 d D U P A 1
S1' S 0.742(2) 0.0897(15) 0.2344(8) 0.046(3) Uani 0.078(3) 1 d D U P A 2
O1' O 0.852(3) 0.020(3) 0.2534(18) 0.047(5) Uani 0.078(3) 1 d D U P A 2
O2' O 0.771(4) 0.151(3) 0.1835(12) 0.053(5) Uani 0.078(3) 1 d D U P A 2
O3' O 0.619(3) 0.028(3) 0.2332(18) 0.042(5) Uani 0.078(3) 1 d D U P A 2
F1' F 0.828(3) 0.251(3) 0.2925(14) 0.038(7) Uani 0.078(3) 1 d D U P A 2
F2' F 0.628(3) 0.267(2) 0.2667(16) 0.059(8) Uani 0.078(3) 1 d D U P A 2
F3' F 0.680(3) 0.151(3) 0.3373(10) 0.052(7) Uani 0.078(3) 1 d D U P A 2
C20' C 0.715(4) 0.195(2) 0.2877(12) 0.044(8) Uani 0.078(3) 1 d D U P A 2
S2 S 0.69274(12) 0.44467(11) 0.47681(5) 0.0297(3) Uani 0.887(4) 1 d D U P B 1
O4 O 0.6337(4) 0.3365(3) 0.4839(2) 0.0533(10) Uani 0.887(4) 1 d D U P B 1
O5 O 0.6055(5) 0.5250(4) 0.4501(2) 0.0542(13) Uani 0.887(4) 1 d D U P B 1
O6 O 0.7671(7) 0.4823(4) 0.52585(18) 0.0535(14) Uani 0.887(4) 1 d D U P B 1
F4 F 0.8896(4) 0.5135(3) 0.41331(16) 0.0760(11) Uani 0.887(4) 1 d D U P B 1
F5 F 0.7696(6) 0.3925(4) 0.37286(13) 0.0851(13) Uani 0.887(4) 1 d D U P B 1
F6 F 0.9058(3) 0.3435(3) 0.43957(15) 0.0609(9) Uani 0.887(4) 1 d D U P B 1
C21 C 0.8214(5) 0.4218(4) 0.42301(19) 0.0412(11) Uani 0.887(4) 1 d D U P B 1
S2' S 0.7166(13) 0.4978(12) 0.4678(5) 0.051(3) Uani 0.113(4) 1 d D U P B 2
O4' O 0.818(3) 0.556(2) 0.4363(11) 0.051(4) Uani 0.113(4) 1 d D U P B 2
O5' O 0.590(3) 0.554(3) 0.4632(19) 0.054(5) Uani 0.113(4) 1 d D U P B 2
O6' O 0.752(6) 0.455(4) 0.5235(14) 0.051(5) Uani 0.113(4) 1 d D U P B 2
F4' F 0.806(4) 0.309(2) 0.4229(15) 0.100(8) Uani 0.113(4) 1 d D U P B 2
F5' F 0.665(4) 0.384(2) 0.3746(12) 0.090(8) Uani 0.113(4) 1 d D U P B 2
F6' F 0.602(4) 0.311(2) 0.4525(15) 0.087(8) Uani 0.113(4) 1 d D U P B 2
C21' C 0.696(3) 0.370(2) 0.4281(13) 0.088(8) Uani 0.113(4) 1 d D U P B 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
N1 C1 1.273(4) . ?
N1 C13 1.475(4) . ?
N1 C4 1.533(4) . ?
N2 C5 1.272(4) . ?
N2 C15 1.469(4) . ?
N2 C8 1.520(4) . ?
C1 C2 1.493(5) . ?
C1 H1 0.9500 . ?
C2 C10 1.517(6) . ?
C2 C9 1.523(5) . ?
C2 C3 1.545(5) . ?
C3 C4 1.539(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C11 1.503(5) . ?
C4 C12 1.515(5) . ?
C5 C6 1.480(5) . ?
C5 H5 0.9500 . ?
C6 C18 1.519(6) . ?
C6 C7 1.533(5) . ?
C6 C19 1.539(5) . ?
C7 C8 1.532(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C17 1.502(5) . ?
C8 C16 1.507(5) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.518(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.516(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
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 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
S1 O1 1.426(3) . ?
S1 O3 1.430(3) . ?
S1 O2 1.435(3) . ?
S1 C20 1.806(4) . ?
F1 C20 1.329(6) . ?
F2 C20 1.323(6) . ?
F3 C20 1.325(6) . ?
S1' O2' 1.42(2) . ?
S1' O3' 1.44(2) . ?
S1' O1' 1.45(2) . ?
S1' C20' 1.78(2) . ?
F1' C20' 1.32(3) . ?
F2' C20' 1.32(3) . ?
F3' C20' 1.31(3) . ?
S2 O6 1.428(4) . ?
S2 O4 1.439(4) . ?
S2 O5 1.440(4) . ?
S2 C21 1.809(5) . ?
F4 C21 1.316(6) . ?
F5 C21 1.316(6) . ?
F6 C21 1.322(6) . ?
S2' O6' 1.43(2) . ?
S2' O4' 1.43(2) . ?
S2' O5' 1.44(2) . ?
S2' C21' 1.80(2) . ?
F4' C21' 1.32(3) . ?
F5' C21' 1.29(3) . ?
F6' C21' 1.31(3) . ?

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
C1 N1 C13 127.0(3) . . ?
C1 N1 C4 112.9(3) . . ?
C13 N1 C4 120.0(3) . . ?
C5 N2 C15 126.9(3) . . ?
C5 N2 C8 113.1(3) . . ?
C15 N2 C8 120.0(2) . . ?
N1 C1 C2 114.7(3) . . ?
N1 C1 H1 122.7 . . ?
C2 C1 H1 122.7 . . ?
C1 C2 C10 108.9(3) . . ?
C1 C2 C9 109.2(3) . . ?
C10 C2 C9 110.6(3) . . ?
C1 C2 C3 101.1(3) . . ?
C10 C2 C3 114.0(3) . . ?
C9 C2 C3 112.5(3) . . ?
C4 C3 C2 107.9(3) . . ?
C4 C3 H3A 110.1 . . ?
C2 C3 H3A 110.1 . . ?
C4 C3 H3B 110.1 . . ?
C2 C3 H3B 110.1 . . ?
H3A C3 H3B 108.4 . . ?
C11 C4 C12 111.5(3) . . ?
C11 C4 N1 109.6(3) . . ?
C12 C4 N1 107.8(3) . . ?
C11 C4 C3 114.0(3) . . ?
C12 C4 C3 112.5(3) . . ?
N1 C4 C3 100.6(3) . . ?
N2 C5 C6 114.8(3) . . ?
N2 C5 H5 122.6 . . ?
C6 C5 H5 122.6 . . ?
C5 C6 C18 109.1(3) . . ?
C5 C6 C7 101.8(3) . . ?
C18 C6 C7 112.2(3) . . ?
C5 C6 C19 110.0(3) . . ?
C18 C6 C19 109.3(3) . . ?
C7 C6 C19 114.1(4) . . ?
C8 C7 C6 108.6(3) . . ?
C8 C7 H7A 110.0 . . ?
C6 C7 H7A 110.0 . . ?
C8 C7 H7B 110.0 . . ?
C6 C7 H7B 110.0 . . ?
H7A C7 H7B 108.3 . . ?
C17 C8 C16 111.6(3) . . ?
C17 C8 N2 109.2(3) . . ?
C16 C8 N2 109.5(3) . . ?
C17 C8 C7 113.4(4) . . ?
C16 C8 C7 111.6(4) . . ?
N2 C8 C7 101.0(3) . . ?
C2 C9 H9A 109.5 . . ?
C2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C10 H10A 109.5 . . ?
C2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 C11 H11A 109.5 . . ?
C4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C4 C12 H12A 109.5 . . ?
C4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 C14 112.4(3) . . ?
N1 C13 H13A 109.1 . . ?
C14 C13 H13A 109.1 . . ?
N1 C13 H13B 109.1 . . ?
C14 C13 H13B 109.1 . . ?
H13A C13 H13B 107.9 . . ?
C15 C14 C13 108.6(3) . . ?
C15 C14 H14A 110.0 . . ?
C13 C14 H14A 110.0 . . ?
C15 C14 H14B 110.0 . . ?
C13 C14 H14B 110.0 . . ?
H14A C14 H14B 108.4 . . ?
N2 C15 C14 112.6(3) . . ?
N2 C15 H15A 109.1 . . ?
C14 C15 H15A 109.1 . . ?
N2 C15 H15B 109.1 . . ?
C14 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
C8 C16 H16A 109.5 . . ?
C8 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C8 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C8 C17 H17A 109.5 . . ?
C8 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C8 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C6 C18 H18A 109.5 . . ?
C6 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C6 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C6 C19 H19A 109.5 . . ?
C6 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C6 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O1 S1 O3 115.7(3) . . ?
O1 S1 O2 114.4(2) . . ?
O3 S1 O2 113.2(2) . . ?
O1 S1 C20 104.8(2) . . ?
O3 S1 C20 102.5(2) . . ?
O2 S1 C20 104.2(2) . . ?
F2 C20 F3 108.8(4) . . ?
F2 C20 F1 106.5(4) . . ?
F3 C20 F1 107.2(4) . . ?
F2 C20 S1 111.5(3) . . ?
F3 C20 S1 112.2(3) . . ?
F1 C20 S1 110.3(3) . . ?
O2' S1' O3' 115(2) . . ?
O2' S1' O1' 113(2) . . ?
O3' S1' O1' 111(2) . . ?
O2' S1' C20' 103.5(18) . . ?
O3' S1' C20' 105(2) . . ?
O1' S1' C20' 109(2) . . ?
F3' C20' F2' 114(3) . . ?
F3' C20' F1' 111(3) . . ?
F2' C20' F1' 105(3) . . ?
F3' C20' S1' 111(2) . . ?
F2' C20' S1' 108(2) . . ?
F1' C20' S1' 107(2) . . ?
O6 S2 O4 114.3(3) . . ?
O6 S2 O5 116.2(3) . . ?
O4 S2 O5 114.0(3) . . ?
O6 S2 C21 102.8(3) . . ?
O4 S2 C21 103.4(2) . . ?
O5 S2 C21 103.9(3) . . ?
F4 C21 F5 106.2(4) . . ?
F4 C21 F6 108.4(5) . . ?
F5 C21 F6 108.3(4) . . ?
F4 C21 S2 111.0(3) . . ?
F5 C21 S2 111.3(4) . . ?
F6 C21 S2 111.4(3) . . ?
O6' S2' O4' 117(3) . . ?
O6' S2' O5' 117(3) . . ?
O4' S2' O5' 111(2) . . ?
O6' S2' C21' 100(2) . . ?
O4' S2' C21' 104.1(16) . . ?
O5' S2' C21' 105(2) . . ?
F5' C21' F6' 108(3) . . ?
F5' C21' F4' 101(3) . . ?
F6' C21' F4' 110(3) . . ?
F5' C21' S2' 114(2) . . ?
F6' C21' S2' 109(2) . . ?
F4' C21' S2' 115(2) . . ?

_refine_diff_density_max         0.584
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_aj1150
_audit_block_doi                 10.5517/ccdc.csd.cc245rx0
_database_code_depnum_ccdc_archive 'CCDC 1971752'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D0CC07385G 2021
loop_
_audit_author_name
_audit_author_address
'HEMANT RAWAT'
;TATA INSTITUTE OF FUNDAMENTAL RESEARCH HYDERABAD
India
;
_audit_update_record             
;
2020-05-25 deposited with the CCDC.	2021-05-04 downloaded from the CCDC.
;
_audit_creation_date             2020-05-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H32 N2'
_chemical_formula_sum            'C18 H32 N2'
_chemical_formula_weight         276.45
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.3706(9)
_cell_length_b                   8.1457(4)
_cell_length_c                   18.6134(11)
_cell_angle_alpha                90
_cell_angle_beta                 91.043(7)
_cell_angle_gamma                90
_cell_volume                     1723.72(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3612
_cell_measurement_temperature    240(2)
_cell_measurement_theta_max      26.1980
_cell_measurement_theta_min      3.6550
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.988
_exptl_absorpt_coefficient_mu    0.062
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.065
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_av_unetI/netI     0.0537
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12263
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.500
_diffrn_ambient_temperature      240.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2445
_reflns_number_total             2958
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2958
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0859
_refine_ls_R_factor_gt           0.0750
_refine_ls_restrained_S_all      1.045
_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)+(0.1181P)²+0.6942P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2041
_refine_ls_wR_factor_ref         0.2127
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.9507(14)
 0.0493(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Others
 Sof(C3')=Sof(H3'A)=Sof(H3'B)=Sof(C4')=Sof(H4'A)=Sof(H4'B)=1-FVAR(1)
 Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(C4)=Sof(H4A)=Sof(H4B)=FVAR(1)
 Sof(C13')=Sof(H13C)=Sof(H13D)=1-FVAR(2)
 Sof(C13)=Sof(H13A)=Sof(H13B)=FVAR(2)
4.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C3'(H3'A,H3'B), C4'(H4'A,H4'B), C6(H6A,H6B),
 C13(H13A,H13B), C13'(H13C,H13D)
4.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C),
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.39462(18) 0.2738(2) 0.67354(10) 0.0436(5) Uani 1 1 d . . . . .
N2 N 0.36884(17) 0.2776(2) 0.82101(10) 0.0417(5) Uani 1 1 d . . . . .
C1 C 0.47914(19) 0.3568(2) 0.71809(12) 0.0355(5) Uani 1 1 d . . . . .
C2 C 0.46709(19) 0.3546(2) 0.78948(12) 0.0353(5) Uani 1 1 d . . . . .
C3 C 0.2831(5) 0.1956(7) 0.7749(2) 0.0421(12) Uani 0.771(14) 1 d . . P A 1
H3A H 0.220592 0.272848 0.760964 0.050 Uiso 0.771(14) 1 calc R . P A 1
H3B H 0.247261 0.104389 0.800925 0.050 Uiso 0.771(14) 1 calc R . P A 1
C4 C 0.3419(5) 0.1314(6) 0.70854(19) 0.0428(13) Uani 0.771(14) 1 d . . P A 1
H4A H 0.402544 0.050771 0.721627 0.051 Uiso 0.771(14) 1 calc R . P A 1
H4B H 0.284104 0.078821 0.676337 0.051 Uiso 0.771(14) 1 calc R . P A 1
C3' C 0.3285(19) 0.130(2) 0.7752(8) 0.051(4) Uani 0.229(14) 1 d . . P A 2
H3'A H 0.393603 0.052995 0.767685 0.061 Uiso 0.229(14) 1 calc R . P A 2
H3'B H 0.263965 0.070795 0.798172 0.061 Uiso 0.229(14) 1 calc R . P A 2
C4' C 0.2900(19) 0.202(3) 0.7087(8) 0.057(5) Uani 0.229(14) 1 d . . P A 2
H4'A H 0.231708 0.288097 0.717728 0.068 Uiso 0.229(14) 1 calc R . P A 2
H4'B H 0.253553 0.118844 0.677556 0.068 Uiso 0.229(14) 1 calc R . P A 2
C5 C 0.4430(3) 0.2410(3) 0.60281(13) 0.0540(7) Uani 1 1 d . . . . .
C6 C 0.5138(3) 0.3981(4) 0.59361(15) 0.0667(8) Uani 1 1 d . . . . .
H6A H 0.463337 0.485731 0.574325 0.080 Uiso 1 1 calc R . . . .
H6B H 0.578125 0.379793 0.560174 0.080 Uiso 1 1 calc R . . . .
C7 C 0.5634(2) 0.4466(3) 0.66788(14) 0.0487(6) Uani 1 1 d . . . . .
C8 C 0.5553(4) 0.6334(3) 0.6748(2) 0.0795(10) Uani 1 1 d . . . . .
H8A H 0.473751 0.667224 0.669738 0.119 Uiso 1 1 calc GR . . . .
H8B H 0.601093 0.684554 0.637462 0.119 Uiso 1 1 calc GR . . . .
H8C H 0.585849 0.666799 0.721525 0.119 Uiso 1 1 calc GR . . . .
C9 C 0.6921(3) 0.3964(6) 0.6742(2) 0.0958(13) Uani 1 1 d . . . . .
H9A H 0.733672 0.434849 0.632342 0.144 Uiso 1 1 calc GR . . . .
H9B H 0.697698 0.277792 0.677054 0.144 Uiso 1 1 calc GR . . . .
H9C H 0.727042 0.444746 0.717161 0.144 Uiso 1 1 calc GR . . . .
C10 C 0.5182(4) 0.0865(4) 0.5998(2) 0.0889(12) Uani 1 1 d . . . . .
H10A H 0.576689 0.088960 0.638392 0.133 Uiso 1 1 calc GR . . . .
H10B H 0.557259 0.081428 0.553972 0.133 Uiso 1 1 calc GR . . . .
H10C H 0.468536 -0.009428 0.605182 0.133 Uiso 1 1 calc GR . . . .
C11 C 0.3450(3) 0.2286(4) 0.54621(15) 0.0709(9) Uani 1 1 d . . . . .
H11A H 0.296975 0.132949 0.555780 0.106 Uiso 1 1 calc GR . . . .
H11B H 0.379021 0.218539 0.499005 0.106 Uiso 1 1 calc GR . . . .
H11C H 0.296560 0.326551 0.547797 0.106 Uiso 1 1 calc GR . . . .
C12 C 0.4004(3) 0.2124(3) 0.89219(14) 0.0538(7) Uani 1 1 d . . . . .
C13 C 0.4750(11) 0.3622(19) 0.9193(5) 0.058(2) Uani 0.56(3) 1 d . . P B 1
H13A H 0.424150 0.445893 0.940282 0.070 Uiso 0.56(3) 1 calc R . P B 1
H13B H 0.533068 0.327293 0.955694 0.070 Uiso 0.56(3) 1 calc R . P B 1
C13' C 0.513(2) 0.303(2) 0.9117(8) 0.069(4) Uani 0.44(3) 1 d . . P B 2
H13C H 0.578849 0.225390 0.915409 0.083 Uiso 0.44(3) 1 calc R . P B 2
H13D H 0.505216 0.358045 0.958169 0.083 Uiso 0.44(3) 1 calc R . P B 2
C14 C 0.5370(2) 0.4310(3) 0.85241(13) 0.0476(6) Uani 1 1 d . . . . .
C15 C 0.6683(3) 0.4200(6) 0.8498(2) 0.1033(15) Uani 1 1 d . . . . .
H15A H 0.696014 0.481725 0.808877 0.155 Uiso 1 1 calc GR . . . .
H15B H 0.691510 0.305981 0.845149 0.155 Uiso 1 1 calc GR . . . .
H15C H 0.702364 0.465236 0.893652 0.155 Uiso 1 1 calc GR . . . .
C16 C 0.5045(5) 0.6097(4) 0.8617(2) 0.1027(14) Uani 1 1 d . . . . .
H16A H 0.527842 0.671154 0.819661 0.154 Uiso 1 1 calc GR . . . .
H16B H 0.544678 0.653393 0.903967 0.154 Uiso 1 1 calc GR . . . .
H16C H 0.420169 0.619165 0.867448 0.154 Uiso 1 1 calc GR . . . .
C17 C 0.2949(4) 0.2103(4) 0.94016(18) 0.0843(11) Uani 1 1 d . . . . .
H17A H 0.262455 0.320128 0.943394 0.126 Uiso 1 1 calc GR . . . .
H17B H 0.318541 0.172786 0.987730 0.126 Uiso 1 1 calc GR . . . .
H17C H 0.235796 0.136573 0.920201 0.126 Uiso 1 1 calc GR . . . .
C18 C 0.4511(4) 0.0393(5) 0.8867(2) 0.0985(13) Uani 1 1 d . . . . .
H18A H 0.390115 -0.035497 0.870009 0.148 Uiso 1 1 calc GR . . . .
H18B H 0.480076 0.004367 0.933608 0.148 Uiso 1 1 calc GR . . . .
H18C H 0.515229 0.039123 0.853069 0.148 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
N1 C1 1.428(3) . ?
N1 C4 1.464(4) . ?
N1 C4' 1.488(15) . ?
N1 C5 1.461(3) . ?
N2 C2 1.417(3) . ?
N2 C3 1.451(4) . ?
N2 C3' 1.542(14) . ?
N2 C12 1.466(3) . ?
C1 C2 1.338(3) . ?
C1 C7 1.536(3) . ?
C2 C14 1.536(3) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 C4 1.508(9) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C3' H3'A 0.9800 . ?
C3' H3'B 0.9800 . ?
C3' C4' 1.43(3) . ?
C4' H4'A 0.9800 . ?
C4' H4'B 0.9800 . ?
C5 C6 1.524(4) . ?
C5 C10 1.523(4) . ?
C5 C11 1.523(4) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 C7 1.535(4) . ?
C7 C8 1.530(4) . ?
C7 C9 1.522(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 H8C 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C12 C13 1.564(11) . ?
C12 C13' 1.517(16) . ?
C12 C17 1.509(5) . ?
C12 C18 1.527(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 C14 1.546(10) . ?
C13' H13C 0.9800 . ?
C13' H13D 0.9800 . ?
C13' C14 1.545(12) . ?
C14 C15 1.497(4) . ?
C14 C16 1.513(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 H17C 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?

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
C1 N1 C4 113.2(2) . . ?
C1 N1 C4' 117.7(5) . . ?
C1 N1 C5 110.5(2) . . ?
C5 N1 C4 114.8(3) . . ?
C5 N1 C4' 129.9(6) . . ?
C2 N2 C3 119.0(2) . . ?
C2 N2 C3' 110.2(6) . . ?
C2 N2 C12 110.62(19) . . ?
C3 N2 C12 121.3(2) . . ?
C12 N2 C3' 106.3(8) . . ?
N1 C1 C7 107.01(19) . . ?
C2 C1 N1 119.3(2) . . ?
C2 C1 C7 133.4(2) . . ?
N2 C2 C14 105.34(19) . . ?
C1 C2 N2 120.9(2) . . ?
C1 C2 C14 133.7(2) . . ?
N2 C3 H3A 109.7 . . ?
N2 C3 H3B 109.7 . . ?
N2 C3 C4 109.9(4) . . ?
H3A C3 H3B 108.2 . . ?
C4 C3 H3A 109.7 . . ?
C4 C3 H3B 109.7 . . ?
N1 C4 C3 106.3(4) . . ?
N1 C4 H4A 110.5 . . ?
N1 C4 H4B 110.5 . . ?
C3 C4 H4A 110.5 . . ?
C3 C4 H4B 110.5 . . ?
H4A C4 H4B 108.7 . . ?
N2 C3' H3'A 111.0 . . ?
N2 C3' H3'B 111.0 . . ?
H3'A C3' H3'B 109.0 . . ?
C4' C3' N2 103.7(16) . . ?
C4' C3' H3'A 111.0 . . ?
C4' C3' H3'B 111.0 . . ?
N1 C4' H4'A 110.1 . . ?
N1 C4' H4'B 110.1 . . ?
C3' C4' N1 107.9(18) . . ?
C3' C4' H4'A 110.1 . . ?
C3' C4' H4'B 110.1 . . ?
H4'A C4' H4'B 108.4 . . ?
N1 C5 C6 99.0(2) . . ?
N1 C5 C10 113.9(2) . . ?
N1 C5 C11 110.7(2) . . ?
C10 C5 C6 113.1(3) . . ?
C11 C5 C6 111.1(2) . . ?
C11 C5 C10 108.9(2) . . ?
C5 C6 H6A 110.2 . . ?
C5 C6 H6B 110.2 . . ?
C5 C6 C7 107.5(2) . . ?
H6A C6 H6B 108.5 . . ?
C7 C6 H6A 110.2 . . ?
C7 C6 H6B 110.2 . . ?
C6 C7 C1 101.7(2) . . ?
C8 C7 C1 112.5(2) . . ?
C8 C7 C6 108.1(2) . . ?
C9 C7 C1 115.8(2) . . ?
C9 C7 C6 109.7(3) . . ?
C9 C7 C8 108.6(3) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C13 97.5(5) . . ?
N2 C12 C13' 103.4(5) . . ?
N2 C12 C17 110.8(3) . . ?
N2 C12 C18 111.1(2) . . ?
C13' C12 C18 98.5(9) . . ?
C17 C12 C13 104.5(5) . . ?
C17 C12 C13' 122.8(9) . . ?
C17 C12 C18 109.5(3) . . ?
C18 C12 C13 122.6(6) . . ?
C12 C13 H13A 110.5 . . ?
C12 C13 H13B 110.5 . . ?
H13A C13 H13B 108.7 . . ?
C14 C13 C12 106.0(5) . . ?
C14 C13 H13A 110.5 . . ?
C14 C13 H13B 110.5 . . ?
C12 C13' H13C 110.0 . . ?
C12 C13' H13D 110.0 . . ?
C12 C13' C14 108.4(8) . . ?
H13C C13' H13D 108.4 . . ?
C14 C13' H13C 110.0 . . ?
C14 C13' H13D 110.0 . . ?
C2 C14 C13 103.3(4) . . ?
C2 C14 C13' 100.1(5) . . ?
C15 C14 C2 117.0(2) . . ?
C15 C14 C13 118.3(6) . . ?
C15 C14 C13' 99.9(9) . . ?
C15 C14 C16 107.9(3) . . ?
C16 C14 C2 110.7(2) . . ?
C16 C14 C13 98.1(6) . . ?
C16 C14 C13' 121.4(10) . . ?
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 . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C12 C18 H18A 109.5 . . ?
C12 C18 H18B 109.5 . . ?
C12 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.9507(14)
2 0.0493(14)

####################################################################### 
# 
# 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_aj0605
_audit_block_doi                 10.5517/ccdc.csd.cc245s59
_database_code_depnum_ccdc_archive 'CCDC 1971760'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D0CC07385G 2021
loop_
_audit_author_name
_audit_author_address
'HEMANT RAWAT'
;TATA INSTITUTE OF FUNDAMENTAL RESEARCH HYDERABAD
India
;
_audit_update_record             
;
2020-04-06 deposited with the CCDC.	2021-05-04 downloaded from the CCDC.
;
_audit_creation_date             2020-04-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H34 N2'
_chemical_formula_sum            'C19 H34 N2'
_chemical_formula_weight         290.48
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   8.6542(3)
_cell_length_b                   11.7196(5)
_cell_length_c                   35.0170(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3551.6(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7744
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      28.6620
_cell_measurement_theta_min      3.1880
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.991
_exptl_absorpt_coefficient_mu    0.063
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84546
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.087
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.894
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            23351
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.894
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.079
_diffrn_reflns_theta_min         2.625
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.894
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -44.00 -13.00   0.50   55.00    --    7.20 -45.00 -57.00   62
  2  ω    -73.00 -47.00   0.50   55.00    --   -7.60 -77.00 115.00   52
  3  ω     50.00  96.00   0.50   55.00    --    7.20  77.00-180.00   92
  4  ω    -24.00   2.00   0.50   55.00    --    7.20 -82.00 -90.00   52
  5  ω     26.00  51.00   0.50   55.00    --    7.20 -82.00 -90.00   50
  6  ω    -23.00  41.00   0.50   55.00    --    7.20 -82.00-120.00  128
  7  ω     51.00  86.00   0.50   55.00    --    7.20  77.00 -60.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3336
_reflns_number_total             4236
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         4236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0511
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0534P)²+1.5509P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1184
_refine_ls_wR_factor_ref         0.1258
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C3(H3A,H3B), C5(H5A,H5B), C7(H7A,H7B), C4(H4A,H4B)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C10(H10A,H10B,H10C), C9(H9A,H9B,
 H9C), C19(H19A,H19B,H19C), C11(H11A,H11B,H11C), C18(H18A,H18B,H18C), C12(H12A,
 H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N2 N 0.60169(13) 0.84035(9) 0.60500(3) 0.0195(3) Uani 1 1 d . . . . .
N1 N 0.53278(12) 0.69267(10) 0.66902(3) 0.0185(3) Uani 1 1 d . . . . .
C2 C 0.48643(14) 0.75523(10) 0.60400(3) 0.0143(3) Uani 1 1 d . . . . .
C1 C 0.44273(14) 0.69631(11) 0.63535(3) 0.0145(3) Uani 1 1 d . . . . .
C15 C 0.44103(15) 0.74366(11) 0.56191(4) 0.0167(3) Uani 1 1 d . . . . .
C8 C 0.29584(14) 0.63012(11) 0.64507(4) 0.0176(3) Uani 1 1 d . . . . .
C14 C 0.59587(16) 0.77602(12) 0.54253(4) 0.0198(3) Uani 1 1 d . . . . .
H14A H 0.659227 0.706801 0.538352 0.024 Uiso 1 1 calc R . . . .
H14B H 0.576014 0.812182 0.517454 0.024 Uiso 1 1 calc R . . . .
C3 C 0.64049(16) 0.90054(11) 0.63966(4) 0.0206(3) Uani 1 1 d . . . . .
H3A H 0.543762 0.919169 0.653409 0.025 Uiso 1 1 calc R . . . .
H3B H 0.691122 0.973443 0.632778 0.025 Uiso 1 1 calc R . . . .
C6 C 0.44456(16) 0.67556(12) 0.70407(4) 0.0211(3) Uani 1 1 d . . . . .
C13 C 0.68160(15) 0.85951(11) 0.56884(4) 0.0190(3) Uani 1 1 d . . . . .
C5 C 0.69763(15) 0.70946(12) 0.66802(4) 0.0200(3) Uani 1 1 d . . . . .
H5A H 0.739847 0.669943 0.645310 0.024 Uiso 1 1 calc R . . . .
H5B H 0.743715 0.673497 0.690924 0.024 Uiso 1 1 calc R . . . .
C7 C 0.28094(16) 0.65896(12) 0.68795(4) 0.0227(3) Uani 1 1 d . . . . .
H7A H 0.219645 0.729566 0.691337 0.027 Uiso 1 1 calc R . . . .
H7B H 0.227981 0.596098 0.701568 0.027 Uiso 1 1 calc R . . . .
C16 C 0.39688(17) 0.62406(12) 0.54860(4) 0.0232(3) Uani 1 1 d . . . . .
H16A H 0.470736 0.568626 0.558884 0.035 Uiso 1 1 calc GR . . . .
H16B H 0.398752 0.621136 0.520631 0.035 Uiso 1 1 calc GR . . . .
H16C H 0.292787 0.605601 0.557723 0.035 Uiso 1 1 calc GR . . . .
C4 C 0.74693(17) 0.83460(12) 0.66667(4) 0.0230(3) Uani 1 1 d . . . . .
H4A H 0.855058 0.840240 0.657633 0.028 Uiso 1 1 calc R . . . .
H4B H 0.741376 0.868021 0.692598 0.028 Uiso 1 1 calc R . . . .
C17 C 0.31466(16) 0.82922(12) 0.55071(4) 0.0219(3) Uani 1 1 d . . . . .
H17A H 0.215913 0.805350 0.561840 0.033 Uiso 1 1 calc GR . . . .
H17B H 0.305362 0.831803 0.522833 0.033 Uiso 1 1 calc GR . . . .
H17C H 0.342008 0.905126 0.560308 0.033 Uiso 1 1 calc GR . . . .
C10 C 0.14673(15) 0.66837(12) 0.62550(4) 0.0229(3) Uani 1 1 d . . . . .
H10A H 0.138298 0.751664 0.626849 0.034 Uiso 1 1 calc GR . . . .
H10B H 0.057942 0.633621 0.638402 0.034 Uiso 1 1 calc GR . . . .
H10C H 0.148331 0.644359 0.598694 0.034 Uiso 1 1 calc GR . . . .
C9 C 0.32011(16) 0.50156(12) 0.63941(4) 0.0225(3) Uani 1 1 d . . . . .
H9A H 0.322757 0.484212 0.612041 0.034 Uiso 1 1 calc GR . . . .
H9B H 0.234977 0.459693 0.651419 0.034 Uiso 1 1 calc GR . . . .
H9C H 0.418104 0.478646 0.651155 0.034 Uiso 1 1 calc GR . . . .
C19 C 0.85339(16) 0.82937(13) 0.57167(4) 0.0257(3) Uani 1 1 d . . . . .
H19A H 0.904744 0.882776 0.589072 0.038 Uiso 1 1 calc GR . . . .
H19B H 0.900807 0.834615 0.546318 0.038 Uiso 1 1 calc GR . . . .
H19C H 0.864564 0.751450 0.581442 0.038 Uiso 1 1 calc GR . . . .
C11 C 0.50021(19) 0.57056(13) 0.72630(4) 0.0299(3) Uani 1 1 d . . . . .
H11A H 0.490285 0.502532 0.710215 0.045 Uiso 1 1 calc GR . . . .
H11B H 0.437222 0.561172 0.749349 0.045 Uiso 1 1 calc GR . . . .
H11C H 0.608687 0.580876 0.733557 0.045 Uiso 1 1 calc GR . . . .
C18 C 0.66670(17) 0.98373(12) 0.55560(4) 0.0272(3) Uani 1 1 d . . . . .
H18A H 0.557142 1.003857 0.553428 0.041 Uiso 1 1 calc GR . . . .
H18B H 0.716799 0.992649 0.530676 0.041 Uiso 1 1 calc GR . . . .
H18C H 0.716641 1.034075 0.574224 0.041 Uiso 1 1 calc GR . . . .
C12 C 0.4521(2) 0.77984(14) 0.73044(4) 0.0323(4) Uani 1 1 d . . . . .
H12A H 0.557997 0.789430 0.739826 0.048 Uiso 1 1 calc GR . . . .
H12B H 0.382132 0.768633 0.752118 0.048 Uiso 1 1 calc GR . . . .
H12C H 0.421039 0.848121 0.716223 0.048 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
N2 C2 1.4112(16) . ?
N2 C3 1.4434(17) . ?
N2 C13 1.4602(16) . ?
N1 C1 1.4138(16) . ?
N1 C6 1.4594(16) . ?
N1 C5 1.4406(17) . ?
C2 C1 1.3510(17) . ?
C2 C15 1.5311(17) . ?
C1 C8 1.5276(17) . ?
C15 C14 1.5492(18) . ?
C15 C16 1.5259(19) . ?
C15 C17 1.5347(18) . ?
C8 C7 1.5445(18) . ?
C8 C10 1.5284(18) . ?
C8 C9 1.5342(19) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C13 1.5351(19) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.5298(19) . ?
C6 C7 1.537(2) . ?
C6 C11 1.534(2) . ?
C6 C12 1.533(2) . ?
C13 C19 1.5313(19) . ?
C13 C18 1.5333(19) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C4 1.528(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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 N2 C3 122.06(11) . . ?
C2 N2 C13 114.95(10) . . ?
C3 N2 C13 122.95(11) . . ?
C1 N1 C6 114.65(11) . . ?
C1 N1 C5 121.43(11) . . ?
C5 N1 C6 123.87(11) . . ?
N2 C2 C15 105.54(10) . . ?
C1 C2 N2 122.61(11) . . ?
C1 C2 C15 131.69(11) . . ?
N1 C1 C8 104.92(10) . . ?
C2 C1 N1 122.60(11) . . ?
C2 C1 C8 132.34(11) . . ?
C2 C15 C14 100.26(10) . . ?
C2 C15 C17 111.78(11) . . ?
C16 C15 C2 116.08(11) . . ?
C16 C15 C14 107.91(11) . . ?
C16 C15 C17 110.10(11) . . ?
C17 C15 C14 110.15(11) . . ?
C1 C8 C7 100.08(10) . . ?
C1 C8 C10 116.98(11) . . ?
C1 C8 C9 110.85(10) . . ?
C10 C8 C7 107.54(11) . . ?
C10 C8 C9 110.22(11) . . ?
C9 C8 C7 110.61(11) . . ?
C15 C14 H14A 110.1 . . ?
C15 C14 H14B 110.1 . . ?
H14A C14 H14B 108.4 . . ?
C13 C14 C15 108.13(10) . . ?
C13 C14 H14A 110.1 . . ?
C13 C14 H14B 110.1 . . ?
N2 C3 H3A 108.7 . . ?
N2 C3 H3B 108.7 . . ?
N2 C3 C4 114.40(11) . . ?
H3A C3 H3B 107.6 . . ?
C4 C3 H3A 108.7 . . ?
C4 C3 H3B 108.7 . . ?
N1 C6 C7 100.99(10) . . ?
N1 C6 C11 111.89(12) . . ?
N1 C6 C12 112.01(12) . . ?
C11 C6 C7 111.97(12) . . ?
C12 C6 C7 111.19(12) . . ?
C12 C6 C11 108.69(12) . . ?
N2 C13 C14 101.16(10) . . ?
N2 C13 C19 111.60(11) . . ?
N2 C13 C18 111.61(11) . . ?
C19 C13 C14 111.17(11) . . ?
C19 C13 C18 108.67(11) . . ?
C18 C13 C14 112.53(11) . . ?
N1 C5 H5A 108.7 . . ?
N1 C5 H5B 108.7 . . ?
N1 C5 C4 114.10(11) . . ?
H5A C5 H5B 107.6 . . ?
C4 C5 H5A 108.7 . . ?
C4 C5 H5B 108.7 . . ?
C8 C7 H7A 110.1 . . ?
C8 C7 H7B 110.1 . . ?
C6 C7 C8 107.93(11) . . ?
C6 C7 H7A 110.1 . . ?
C6 C7 H7B 110.1 . . ?
H7A C7 H7B 108.4 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C3 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
C5 C4 C3 109.62(11) . . ?
C5 C4 H4A 109.7 . . ?
C5 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C13 C19 H19A 109.5 . . ?
C13 C19 H19B 109.5 . . ?
C13 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C6 C12 H12A 109.5 . . ?
C6 C12 H12B 109.5 . . ?
C6 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_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
;
####################################################################### 
# 
# 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_AJ0650
_audit_block_doi                 10.5517/ccdc.csd.cc245s7c
_database_code_depnum_ccdc_archive 'CCDC 1971762'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D0CC07385G 2021
loop_
_audit_author_name
_audit_author_address
'HEMANT RAWAT'
;TATA INSTITUTE OF FUNDAMENTAL RESEARCH HYDERABAD
India
;
_audit_update_record             
;
2020-05-21 deposited with the CCDC.	2021-05-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H34 N2, 2(C F3 O3 S)'
_chemical_formula_sum            'C21 H34 F6 N2 O6 S2'
_chemical_formula_weight         588.62

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.9365(2)
_cell_length_b                   16.2526(3)
_cell_length_c                   18.4341(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2677.39(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    20173
_cell_measurement_theta_min      2.7360
_cell_measurement_theta_max      28.5630

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_F_000             1232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.279
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.53412
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40905
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.506
_diffrn_reflns_theta_max         28.272
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6385
_reflns_number_gt                6026
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.737
_reflns_Friedel_fraction_max     0.930
_reflns_Friedel_fraction_full    1.000

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0276P)²+1.9241P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.43(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6385
_refine_ls_number_parameters     511
_refine_ls_number_restraints     332
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.0984
_refine_ls_wR_factor_gt          0.0970
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_restrained_S_all      1.177
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N2 N 0.8009(3) 0.56783(14) 0.69325(15) 0.0247(5) Uani 1 1 d . . . . .
N1 N 0.8256(3) 0.63879(13) 0.83574(13) 0.0238(5) Uani 1 1 d . . . . .
C1 C 0.7210(3) 0.65504(16) 0.78996(17) 0.0251(6) Uani 1 1 d . . . . .
C2 C 0.6899(3) 0.59427(17) 0.7315(2) 0.0315(7) Uani 1 1 d . . . . .
C3 C 0.9574(3) 0.59480(18) 0.70342(16) 0.0219(6) Uani 1 1 d . . . . .
H3A H 0.961032 0.655614 0.705927 0.026 Uiso 1 1 calc R U . . .
H3B H 1.018170 0.577011 0.661357 0.026 Uiso 1 1 calc R U . . .
C4 C 1.0231(3) 0.55852(18) 0.77295(15) 0.0230(6) Uani 1 1 d . . . . .
H4A H 1.053504 0.500884 0.763768 0.028 Uiso 1 1 calc R U . . .
H4B H 1.113734 0.589945 0.786521 0.028 Uiso 1 1 calc R U . . .
C5 C 0.9124(4) 0.56040(17) 0.83606(16) 0.0246(6) Uani 1 1 d . . . . .
H5A H 0.842792 0.513226 0.832061 0.029 Uiso 1 1 calc R U . . .
H5B H 0.967420 0.555223 0.882448 0.029 Uiso 1 1 calc R U . . .
C6 C 0.8532(5) 0.70716(18) 0.89033(17) 0.0336(8) Uani 1 1 d . . . . .
C7 C 0.7650(4) 0.77751(17) 0.85402(18) 0.0354(8) Uani 1 1 d . . . . .
H7A H 0.834118 0.814007 0.827071 0.042 Uiso 1 1 calc R U . . .
H7B H 0.712848 0.810678 0.891299 0.042 Uiso 1 1 calc R U . . .
C8 C 0.6499(4) 0.73893(17) 0.8014(2) 0.0343(7) Uani 1 1 d . . . . .
C9 C 0.6399(4) 0.78772(19) 0.7306(2) 0.0372(8) Uani 1 1 d . . . . .
H9A H 0.738526 0.789317 0.707441 0.056 Uiso 1 1 calc R U . . .
H9B H 0.606710 0.843949 0.741103 0.056 Uiso 1 1 calc R U . . .
H9C H 0.568032 0.761161 0.698006 0.056 Uiso 1 1 calc R U . . .
C10 C 0.4946(5) 0.7318(2) 0.8375(3) 0.0577(14) Uani 1 1 d . . . . .
H10A H 0.424648 0.705352 0.803781 0.087 Uiso 1 1 calc R U . . .
H10B H 0.457759 0.786822 0.849820 0.087 Uiso 1 1 calc R U . . .
H10C H 0.502685 0.698627 0.881693 0.087 Uiso 1 1 calc R U . . .
C11 C 0.7891(6) 0.6791(2) 0.96319(19) 0.0516(11) Uani 1 1 d . . . . .
H11A H 0.683861 0.663599 0.956961 0.077 Uiso 1 1 calc R U . . .
H11B H 0.796332 0.724151 0.998358 0.077 Uiso 1 1 calc R U . . .
H11C H 0.845857 0.631615 0.980921 0.077 Uiso 1 1 calc R U . . .
C12 C 1.0187(5) 0.7247(2) 0.89541(19) 0.0391(8) Uani 1 1 d . . . . .
H12A H 1.069432 0.677838 0.918184 0.059 Uiso 1 1 calc R U . . .
H12B H 1.034887 0.774169 0.924729 0.059 Uiso 1 1 calc R U . . .
H12C H 1.059381 0.733326 0.846633 0.059 Uiso 1 1 calc R U . . .
C13 C 0.7735(16) 0.5110(10) 0.6240(8) 0.025(3) Uani 0.49(2) 1 d D . P A 1
C14 C 0.6109(11) 0.4898(6) 0.6435(8) 0.028(2) Uani 0.49(2) 1 d D . P A 1
H14A H 0.607214 0.436235 0.669049 0.033 Uiso 0.49(2) 1 calc R U P A 1
H14B H 0.550109 0.485338 0.598768 0.033 Uiso 0.49(2) 1 calc R U P A 1
C15 C 0.5468(9) 0.5586(5) 0.6931(8) 0.024(2) Uani 0.49(2) 1 d D . P A 1
C16 C 0.4570(8) 0.5238(4) 0.7572(9) 0.029(3) Uani 0.49(2) 1 d D . P A 1
H16A H 0.519050 0.484502 0.784116 0.043 Uiso 0.49(2) 1 calc R U P A 1
H16B H 0.367442 0.495803 0.738998 0.043 Uiso 0.49(2) 1 calc R U P A 1
H16C H 0.427241 0.568822 0.789514 0.043 Uiso 0.49(2) 1 calc R U P A 1
C17 C 0.4525(10) 0.6210(5) 0.6491(8) 0.033(3) Uani 0.49(2) 1 d D . P A 1
H17A H 0.410333 0.662281 0.682025 0.050 Uiso 0.49(2) 1 calc R U P A 1
H17B H 0.371089 0.591949 0.624322 0.050 Uiso 0.49(2) 1 calc R U P A 1
H17C H 0.516272 0.648183 0.613144 0.050 Uiso 0.49(2) 1 calc R U P A 1
C18 C 0.7907(17) 0.5612(8) 0.5540(6) 0.041(3) Uani 0.49(2) 1 d D . P A 1
H18A H 0.720280 0.607465 0.554659 0.062 Uiso 0.49(2) 1 calc R U P A 1
H18B H 0.769510 0.526042 0.512071 0.062 Uiso 0.49(2) 1 calc R U P A 1
H18C H 0.893193 0.582270 0.550595 0.062 Uiso 0.49(2) 1 calc R U P A 1
C13' C 0.7371(13) 0.5064(7) 0.6417(7) 0.016(2) Uani 0.51(2) 1 d D . P A 2
C14' C 0.5891(9) 0.4812(4) 0.6760(7) 0.0226(19) Uani 0.51(2) 1 d D . P A 2
H14C H 0.602094 0.429793 0.704133 0.027 Uiso 0.51(2) 1 calc R U P A 2
H14D H 0.513176 0.471433 0.637912 0.027 Uiso 0.51(2) 1 calc R U P A 2
C15' C 0.5374(8) 0.5519(4) 0.7269(7) 0.0203(19) Uani 0.51(2) 1 d D . P A 2
C16' C 0.4697(10) 0.5197(5) 0.7982(8) 0.033(2) Uani 0.51(2) 1 d D . P A 2
H16D H 0.544223 0.486480 0.823963 0.049 Uiso 0.51(2) 1 calc R U P A 2
H16E H 0.381746 0.485824 0.787462 0.049 Uiso 0.51(2) 1 calc R U P A 2
H16F H 0.439936 0.566346 0.828704 0.049 Uiso 0.51(2) 1 calc R U P A 2
C17' C 0.4280(9) 0.6101(5) 0.6888(8) 0.037(3) Uani 0.51(2) 1 d D . P A 2
H17D H 0.400405 0.654808 0.721800 0.055 Uiso 0.51(2) 1 calc R U P A 2
H17E H 0.337961 0.579545 0.674715 0.055 Uiso 0.51(2) 1 calc R U P A 2
H17F H 0.475544 0.633066 0.645365 0.055 Uiso 0.51(2) 1 calc R U P A 2
C18' C 0.7298(14) 0.5527(5) 0.5715(5) 0.029(2) Uani 0.51(2) 1 d D . P A 2
H18D H 0.663393 0.600320 0.576964 0.044 Uiso 0.51(2) 1 calc R U P A 2
H18E H 0.690900 0.516531 0.533358 0.044 Uiso 0.51(2) 1 calc R U P A 2
H18F H 0.830244 0.571605 0.558172 0.044 Uiso 0.51(2) 1 calc R U P A 2
C19 C 0.8601(5) 0.4348(2) 0.63108(19) 0.0389(8) Uani 1 1 d . . . . .
H19A H 0.964082 0.444973 0.616751 0.058 Uiso 1 1 calc R U . A 1
H19B H 0.816907 0.392339 0.599643 0.058 Uiso 1 1 calc R U . A 1
H19C H 0.857286 0.416037 0.681600 0.058 Uiso 1 1 calc R U . A 1
S1 S 1.1560(8) 0.8188(5) 0.6959(4) 0.0205(9) Uani 0.522(12) 1 d D U P B 1
O1 O 1.2649(9) 0.8817(5) 0.7085(5) 0.0390(18) Uani 0.522(12) 1 d D U P B 1
O2 O 0.9982(12) 0.8374(10) 0.7019(9) 0.061(4) Uani 0.522(12) 1 d D U P B 1
O3 O 1.1944(17) 0.7436(7) 0.7304(8) 0.047(3) Uani 0.522(12) 1 d D U P B 1
F1 F 1.1457(13) 0.8645(6) 0.5632(4) 0.106(3) Uani 0.522(12) 1 d D U P B 1
F2 F 1.3160(10) 0.7767(4) 0.5838(4) 0.067(2) Uani 0.522(12) 1 d D U P B 1
F3 F 1.0946(19) 0.7321(9) 0.5807(5) 0.155(5) Uani 0.522(12) 1 d D U P B 1
C20 C 1.1753(14) 0.7944(6) 0.6003(5) 0.052(3) Uani 0.522(12) 1 d D . P B 1
S1' S 1.1335(9) 0.8185(6) 0.6821(5) 0.0231(12) Uani 0.478(12) 1 d D U P B 2
O1' O 1.2457(12) 0.8815(5) 0.6760(6) 0.048(2) Uani 0.478(12) 1 d D U P B 2
O2' O 0.9957(14) 0.8512(8) 0.7089(9) 0.035(2) Uani 0.478(12) 1 d D U P B 2
O3' O 1.1752(17) 0.7413(7) 0.7145(8) 0.034(3) Uani 0.478(12) 1 d D U P B 2
F1' F 1.0502(11) 0.8581(4) 0.5504(3) 0.061(2) Uani 0.478(12) 1 d D U P B 2
F2' F 1.2229(16) 0.7661(5) 0.5569(5) 0.082(3) Uani 0.478(12) 1 d D U P B 2
F3' F 0.9931(13) 0.7382(4) 0.5831(4) 0.070(3) Uani 0.478(12) 1 d D U P B 2
C20' C 1.0964(16) 0.7915(6) 0.5870(5) 0.047(3) Uani 0.478(12) 1 d D U P B 2
S2 S 0.25527(13) 0.54023(5) 1.01113(4) 0.0386(2) Uani 1 1 d . . . . .
O4 O 0.3499(4) 0.59972(17) 0.97790(15) 0.0540(8) Uani 1 1 d . . . . .
O5 O 0.0977(4) 0.5568(2) 1.00277(15) 0.0561(8) Uani 1 1 d . . . . .
O6 O 0.2979(4) 0.51390(16) 1.08274(13) 0.0469(7) Uani 1 1 d . . . . .
F4 F 0.2677(12) 0.4652(6) 0.8835(3) 0.059(2) Uani 0.485(13) 1 d D . P C 1
F5 F 0.3818(9) 0.4163(4) 0.9570(3) 0.043(2) Uani 0.485(13) 1 d D . P C 1
F6 F 0.1560(9) 0.3882(3) 0.9921(3) 0.0469(19) Uani 0.485(13) 1 d D . P C 1
C21 C 0.2420(13) 0.4449(5) 0.9615(4) 0.0275(19) Uani 0.485(13) 1 d D . P C 1
F4' F 0.1946(9) 0.4559(4) 0.8938(3) 0.0425(16) Uani 0.515(13) 1 d D . P C 2
F5' F 0.4667(11) 0.4430(6) 0.9448(4) 0.072(3) Uani 0.515(13) 1 d D . P C 2
F6' F 0.2614(14) 0.3830(3) 0.9774(4) 0.076(4) Uani 0.515(13) 1 d D . P C 2
C21' C 0.3214(16) 0.4528(7) 0.9508(5) 0.042(2) Uani 0.515(13) 1 d D . P C 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
N2 C2 1.290(4) . ?
N2 C3 1.477(4) . ?
N2 C13' 1.491(13) . ?
N2 C13 1.595(15) . ?
N1 C1 1.286(4) . ?
N1 C5 1.492(4) . ?
N1 C6 1.519(4) . ?
C1 C2 1.489(4) . ?
C1 C8 1.519(4) . ?
C2 C15' 1.529(8) . ?
C2 C15 1.572(8) . ?
C3 C4 1.528(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.527(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C12 1.509(6) . ?
C6 C11 1.530(4) . ?
C6 C7 1.542(5) . ?
C7 C8 1.547(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.529(5) . ?
C8 C10 1.543(5) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C19 1.467(15) . ?
C13 C18 1.534(13) . ?
C13 C14 1.536(13) . ?
C14 C15 1.555(10) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.537(11) . ?
C15 C17 1.548(10) . ?
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 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C13' C18' 1.499(11) . ?
C13' C14' 1.522(11) . ?
C13' C19 1.614(12) . ?
C14' C15' 1.553(9) . ?
C14' H14C 0.9900 . ?
C14' H14D 0.9900 . ?
C15' C17' 1.531(10) . ?
C15' C16' 1.539(10) . ?
C16' H16D 0.9800 . ?
C16' H16E 0.9800 . ?
C16' H16F 0.9800 . ?
C17' H17D 0.9800 . ?
C17' H17E 0.9800 . ?
C17' H17F 0.9800 . ?
C18' H18D 0.9800 . ?
C18' H18E 0.9800 . ?
C18' H18F 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
S1 O3 1.421(11) . ?
S1 O1 1.430(9) . ?
S1 O2 1.447(10) . ?
S1 C20 1.815(10) . ?
F1 C20 1.356(11) . ?
F2 C20 1.326(12) . ?
F3 C20 1.294(12) . ?
S1' O2' 1.429(12) . ?
S1' O1' 1.437(10) . ?
S1' O3' 1.440(11) . ?
S1' C20' 1.838(12) . ?
F1' C20' 1.341(10) . ?
F2' C20' 1.325(13) . ?
F3' C20' 1.268(14) . ?
S2 O4 1.423(3) . ?
S2 O6 1.439(2) . ?
S2 O5 1.442(3) . ?
S2 C21 1.803(7) . ?
S2 C21' 1.899(11) . ?
F4 C21 1.492(10) . ?
F5 C21 1.335(9) . ?
F6 C21 1.326(10) . ?
F4' C21' 1.546(12) . ?
F5' C21' 1.313(12) . ?
F6' C21' 1.346(12) . ?

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 N2 C3 124.0(3) . . ?
C2 N2 C13' 106.1(5) . . ?
C3 N2 C13' 129.9(5) . . ?
C2 N2 C13 120.8(6) . . ?
C3 N2 C13 114.8(5) . . ?
C1 N1 C5 123.8(2) . . ?
C1 N1 C6 113.7(2) . . ?
C5 N1 C6 122.5(3) . . ?
N1 C1 C2 118.4(2) . . ?
N1 C1 C8 113.4(3) . . ?
C2 C1 C8 128.1(3) . . ?
N2 C2 C1 118.2(3) . . ?
N2 C2 C15' 120.3(4) . . ?
C1 C2 C15' 120.4(5) . . ?
N2 C2 C15 104.9(5) . . ?
C1 C2 C15 136.3(4) . . ?
N2 C3 C4 110.8(2) . . ?
N2 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C5 C4 C3 112.5(2) . . ?
C5 C4 H4A 109.1 . . ?
C3 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
C3 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
N1 C5 C4 110.5(2) . . ?
N1 C5 H5A 109.5 . . ?
C4 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C12 C6 N1 109.8(3) . . ?
C12 C6 C11 111.7(3) . . ?
N1 C6 C11 107.6(2) . . ?
C12 C6 C7 112.9(3) . . ?
N1 C6 C7 99.9(3) . . ?
C11 C6 C7 114.2(3) . . ?
C6 C7 C8 108.2(2) . . ?
C6 C7 H7A 110.1 . . ?
C8 C7 H7A 110.1 . . ?
C6 C7 H7B 110.1 . . ?
C8 C7 H7B 110.1 . . ?
H7A C7 H7B 108.4 . . ?
C1 C8 C9 111.8(3) . . ?
C1 C8 C10 111.6(3) . . ?
C9 C8 C10 110.7(3) . . ?
C1 C8 C7 99.9(3) . . ?
C9 C8 C7 111.3(3) . . ?
C10 C8 C7 111.0(3) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C6 C12 H12A 109.5 . . ?
C6 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C6 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C19 C13 C18 118.1(9) . . ?
C19 C13 C14 106.8(10) . . ?
C18 C13 C14 114.3(10) . . ?
C19 C13 N2 109.7(9) . . ?
C18 C13 N2 110.5(11) . . ?
C14 C13 N2 95.0(7) . . ?
C13 C14 C15 109.0(8) . . ?
C13 C14 H14A 109.9 . . ?
C15 C14 H14A 109.9 . . ?
C13 C14 H14B 109.9 . . ?
C15 C14 H14B 109.9 . . ?
H14A C14 H14B 108.3 . . ?
C16 C15 C17 111.1(7) . . ?
C16 C15 C14 112.3(7) . . ?
C17 C15 C14 111.3(7) . . ?
C16 C15 C2 102.4(6) . . ?
C17 C15 C2 115.9(6) . . ?
C14 C15 C2 103.3(6) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N2 C13' C18' 103.4(8) . . ?
N2 C13' C14' 104.3(7) . . ?
C18' C13' C14' 117.2(8) . . ?
N2 C13' C19 107.4(8) . . ?
C18' C13' C19 106.7(7) . . ?
C14' C13' C19 116.6(8) . . ?
C13' C14' C15' 108.1(7) . . ?
C13' C14' H14C 110.1 . . ?
C15' C14' H14C 110.1 . . ?
C13' C14' H14D 110.1 . . ?
C15' C14' H14D 110.1 . . ?
H14C C14' H14D 108.4 . . ?
C2 C15' C17' 108.4(6) . . ?
C2 C15' C16' 117.2(6) . . ?
C17' C15' C16' 110.5(6) . . ?
C2 C15' C14' 95.8(5) . . ?
C17' C15' C14' 111.7(7) . . ?
C16' C15' C14' 112.4(6) . . ?
C15' C16' H16D 109.5 . . ?
C15' C16' H16E 109.5 . . ?
H16D C16' H16E 109.5 . . ?
C15' C16' H16F 109.5 . . ?
H16D C16' H16F 109.5 . . ?
H16E C16' H16F 109.5 . . ?
C15' C17' H17D 109.5 . . ?
C15' C17' H17E 109.5 . . ?
H17D C17' H17E 109.5 . . ?
C15' C17' H17F 109.5 . . ?
H17D C17' H17F 109.5 . . ?
H17E C17' H17F 109.5 . . ?
C13' C18' H18D 109.5 . . ?
C13' C18' H18E 109.5 . . ?
H18D C18' H18E 109.5 . . ?
C13' C18' H18F 109.5 . . ?
H18D C18' H18F 109.5 . . ?
H18E C18' H18F 109.5 . . ?
C13 C19 H19A 109.5 . . ?
C13 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C13 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O3 S1 O1 112.2(8) . . ?
O3 S1 O2 112.4(10) . . ?
O1 S1 O2 120.1(9) . . ?
O3 S1 C20 102.9(8) . . ?
O1 S1 C20 104.5(6) . . ?
O2 S1 C20 102.2(8) . . ?
F3 C20 F2 107.2(10) . . ?
F3 C20 F1 114.1(12) . . ?
F2 C20 F1 104.5(8) . . ?
F3 C20 S1 113.0(7) . . ?
F2 C20 S1 111.1(8) . . ?
F1 C20 S1 106.7(7) . . ?
O2' S1' O1' 111.3(9) . . ?
O2' S1' O3' 113.8(11) . . ?
O1' S1' O3' 118.2(8) . . ?
O2' S1' C20' 105.2(8) . . ?
O1' S1' C20' 102.8(7) . . ?
O3' S1' C20' 103.5(8) . . ?
F3' C20' F2' 112.6(10) . . ?
F3' C20' F1' 107.4(10) . . ?
F2' C20' F1' 107.7(8) . . ?
F3' C20' S1' 110.4(7) . . ?
F2' C20' S1' 108.6(10) . . ?
F1' C20' S1' 110.0(8) . . ?
O4 S2 O6 116.09(19) . . ?
O4 S2 O5 114.04(19) . . ?
O6 S2 O5 114.32(18) . . ?
O4 S2 C21 113.9(3) . . ?
O6 S2 C21 103.1(3) . . ?
O5 S2 C21 92.4(4) . . ?
O4 S2 C21' 94.1(4) . . ?
O6 S2 C21' 103.4(3) . . ?
O5 S2 C21' 112.4(4) . . ?
F6 C21 F5 109.1(6) . . ?
F6 C21 F4 130.8(9) . . ?
F5 C21 F4 82.7(8) . . ?
F6 C21 S2 114.8(5) . . ?
F5 C21 S2 105.6(6) . . ?
F4 C21 S2 106.8(6) . . ?
F5' C21' F6' 108.8(10) . . ?
F5' C21' F4' 132.1(10) . . ?
F6' C21' F4' 89.1(8) . . ?
F5' C21' S2 116.6(7) . . ?
F6' C21' S2 107.0(7) . . ?
F4' C21' S2 98.4(7) . . ?

_refine_diff_density_max         0.351
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_aj0625
_audit_block_doi                 10.5517/ccdc.csd.cc245s6b
_database_code_depnum_ccdc_archive 'CCDC 1971761'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D0CC07385G 2021
loop_
_audit_author_name
_audit_author_address
'HEMANT RAWAT'
;TATA INSTITUTE OF FUNDAMENTAL RESEARCH HYDERABAD
India
;
_audit_update_record             
;
2020-04-06 deposited with the CCDC.	2021-05-04 downloaded from the CCDC.
;
_audit_creation_date             2020-04-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C F3 O3 S, C19 H34 N2'
_chemical_formula_sum            'C20 H34 F3 N2 O3 S'
_chemical_formula_weight         439.55
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.7269(5)
_cell_length_b                   16.6330(3)
_cell_length_c                   16.7087(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.073(2)
_cell_angle_gamma                90
_cell_volume                     4370.75(19)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    25604
_cell_measurement_temperature    119.98(10)
_cell_measurement_theta_max      28.7530
_cell_measurement_theta_min      2.7240
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1880
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            72306
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.957
_diffrn_reflns_theta_min         2.590
_diffrn_ambient_temperature      119.98(10)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -15.00  23.00   0.50   50.00    --    7.20 -57.00 150.00   76
  2  ω    -72.00  35.00   0.50   50.00    --    7.20 -57.00 -60.00  214
  3  ω     63.00  94.00   0.50   50.00    --    7.20  77.00-150.00   62
  4  ω     50.00  83.00   0.50   50.00    --    7.20  77.00-180.00   66
  5  ω     69.00  96.00   0.50   50.00    --    7.20  77.00 -90.00   54
  6  ω     51.00  81.00   0.50   50.00    --    7.20  77.00 -60.00   60
  7  ω     46.00  87.00   0.50   50.00    --    7.20  57.00  30.00   82
  8  ω     50.00  75.00   0.50   50.00    --    7.20  77.00   0.00   50
  9  ω    -63.00  31.00   0.50   50.00    --   -7.60 -82.00 120.00  188
 10  ω    -81.00  17.00   0.50   50.00    --   -7.60 -38.00 150.00  196
 11  ω    -63.00  -1.00   0.50   50.00    --   -7.60 -82.00  30.00  124
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9188
_reflns_number_total             10578
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     540
_refine_ls_number_reflns         10578
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0378
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0457P)²+0.9664P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.0929
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.8033(6)
 0.1967(6)
2. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C4(H4A,H4B), C26(H26A,H26B), C23(H23A,H23B), C5(H5A,H5B),
 C3(H3A,H3B), C14(H14A,H14B), C24(H24A,H24B), C33(H33A,H33B), C7(H7A,H7B)
3.b Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C18(H18A,H18B,H18C), C35(H35A,H35B,
 H35C), C30(H30A,H30B,H30C), C9(H9A,H9B,H9C), C31(H31A,H31B,H31C), C37(H37A,
 H37B,H37C), C38(H38A,H38B,H38C), C19(H19A,H19B,H19C), C36(H36A,H36B,H36C),
 C10(H10A,H10B,H10C), C17(H17A,H17B,H17C), C16(H16A,H16B,H16C), C12(H12A,H12B,
 H12C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S2 S 0.12742(3) 0.81165(2) 0.46715(2) 0.01920(9) Uani 1 1 d . . . . .
S1 S 0.62490(3) 0.80679(2) 0.30695(2) 0.02265(9) Uani 1 1 d . . . . .
F6 F 0.11846(10) 0.66166(7) 0.51675(7) 0.0526(3) Uani 1 1 d . . . . .
F5 F 0.21966(8) 0.68410(7) 0.43481(9) 0.0470(3) Uani 1 1 d . . . . .
F2 F 0.70791(8) 0.67046(6) 0.32354(8) 0.0429(3) Uani 1 1 d . . . . .
F4 F 0.09247(9) 0.67672(6) 0.39154(7) 0.0444(3) Uani 1 1 d . . . . .
F3 F 0.57341(9) 0.65920(7) 0.33427(9) 0.0555(4) Uani 1 1 d . . . . .
F1 F 0.62964(10) 0.67581(7) 0.21980(7) 0.0550(4) Uani 1 1 d . . . . .
O4 O 0.15368(9) 0.84450(7) 0.39190(7) 0.0338(3) Uani 1 1 d . . . . .
N1 N 0.36908(8) 0.82940(7) 0.67922(8) 0.0181(3) Uani 1 1 d . . . . .
O5 O 0.18375(8) 0.82772(8) 0.53310(8) 0.0333(3) Uani 1 1 d . . . . .
O1 O 0.54243(9) 0.82314(8) 0.27464(10) 0.0414(3) Uani 1 1 d . . . . .
O6 O 0.03869(8) 0.81993(8) 0.48474(9) 0.0384(3) Uani 1 1 d . . . . .
N3 N 0.82900(8) 0.83870(7) 0.58282(8) 0.0167(3) Uani 1 1 d . . . . .
N4 N 0.88608(8) 0.67862(7) 0.59579(7) 0.0158(2) Uani 1 1 d . . . . .
N2 N 0.34180(8) 0.66686(7) 0.64075(8) 0.0172(3) Uani 1 1 d . . . . .
O2 O 0.69468(10) 0.83538(9) 0.26026(12) 0.0560(5) Uani 1 1 d . . . . .
O3 O 0.63281(11) 0.81866(8) 0.39145(8) 0.0469(4) Uani 1 1 d . . . . .
C22 C 0.87428(11) 0.69611(9) 0.51066(8) 0.0190(3) Uani 1 1 d . . . . .
H22A H 0.884143 0.646420 0.479398 0.023 Uiso 1 1 calc R . . . .
H22B H 0.917021 0.736331 0.493708 0.023 Uiso 1 1 calc R . . . .
C39 C 0.63426(10) 0.69826(9) 0.29599(9) 0.0211(3) Uani 1 1 d . . . . .
C8 C 0.42504(10) 0.86518(9) 0.55468(10) 0.0227(3) Uani 1 1 d . . . . .
C21 C 0.90592(9) 0.73512(9) 0.65119(8) 0.0141(3) Uani 1 1 d . . . . .
C20 C 0.88880(9) 0.81701(8) 0.63676(8) 0.0145(3) Uani 1 1 d . . . . .
C40 C 0.13969(11) 0.70318(9) 0.45203(9) 0.0222(3) Uani 1 1 d . . . . .
C27 C 0.93063(10) 0.89376(9) 0.66977(9) 0.0180(3) Uani 1 1 d . . . . .
C25 C 0.83156(10) 0.92462(9) 0.55817(9) 0.0201(3) Uani 1 1 d . . . . .
C6 C 0.35260(11) 0.91739(9) 0.67614(11) 0.0260(4) Uani 1 1 d . . . . .
C4 C 0.27624(11) 0.73694(11) 0.75585(10) 0.0279(4) Uani 1 1 d . . . . .
H4A H 0.228004 0.773022 0.768407 0.034 Uiso 1 1 calc R . . . .
H4B H 0.279270 0.694938 0.797745 0.034 Uiso 1 1 calc R . . . .
C26 C 0.91387(10) 0.95155(9) 0.59885(10) 0.0215(3) Uani 1 1 d . . . . .
H26A H 0.908166 1.007450 0.618462 0.026 Uiso 1 1 calc R . . . .
H26B H 0.961711 0.949435 0.560455 0.026 Uiso 1 1 calc R . . . .
C23 C 0.78572(10) 0.72803(10) 0.49203(9) 0.0227(3) Uani 1 1 d . . . . .
H23A H 0.785966 0.756009 0.439741 0.027 Uiso 1 1 calc R . . . .
H23B H 0.744856 0.682855 0.488924 0.027 Uiso 1 1 calc R . . . .
C28 C 1.02599(10) 0.88886(10) 0.68570(10) 0.0238(3) Uani 1 1 d . . . . .
H28A H 1.036039 0.860140 0.736044 0.036 Uiso 1 1 calc GR . . . .
H28B H 1.049522 0.943277 0.689549 0.036 Uiso 1 1 calc GR . . . .
H28C H 1.053684 0.860004 0.641737 0.036 Uiso 1 1 calc GR . . . .
C1 C 0.39954(9) 0.79679(9) 0.61130(9) 0.0156(3) Uani 1 1 d . . . . .
C32 C 0.88286(11) 0.59509(9) 0.62701(9) 0.0214(3) Uani 1 1 d . . . . .
C2 C 0.39900(9) 0.71256(9) 0.60141(8) 0.0149(3) Uani 1 1 d . . . . .
C13 C 0.36211(11) 0.57969(9) 0.64340(10) 0.0240(3) Uani 1 1 d . . . . .
C5 C 0.35872(11) 0.78471(10) 0.75427(9) 0.0230(3) Uani 1 1 d . . . . .
H5A H 0.359290 0.822931 0.799687 0.028 Uiso 1 1 calc R . . . .
H5B H 0.407293 0.747466 0.761085 0.028 Uiso 1 1 calc R . . . .
C3 C 0.26275(10) 0.69818(10) 0.67432(10) 0.0223(3) Uani 1 1 d . . . . .
H3A H 0.221293 0.653704 0.679561 0.027 Uiso 1 1 calc R . . . .
H3B H 0.238437 0.738443 0.637141 0.027 Uiso 1 1 calc R . . . .
C15 C 0.45844(10) 0.65673(9) 0.55443(9) 0.0214(3) Uani 1 1 d . . . . .
C34 C 0.94294(10) 0.69254(9) 0.72432(9) 0.0191(3) Uani 1 1 d . . . . .
C29 C 0.88396(11) 0.92465(10) 0.74501(10) 0.0259(3) Uani 1 1 d . . . . .
H29A H 0.822406 0.921983 0.736223 0.039 Uiso 1 1 calc GR . . . .
H29B H 0.900614 0.980446 0.755493 0.039 Uiso 1 1 calc GR . . . .
H29C H 0.899257 0.891123 0.791064 0.039 Uiso 1 1 calc GR . . . .
C18 C 0.29607(13) 0.53070(10) 0.59595(13) 0.0373(5) Uani 1 1 d . . . . .
H18A H 0.240763 0.534092 0.622687 0.056 Uiso 1 1 calc GR . . . .
H18B H 0.314163 0.474377 0.593333 0.056 Uiso 1 1 calc GR . . . .
H18C H 0.291248 0.552425 0.541615 0.056 Uiso 1 1 calc GR . . . .
C14 C 0.45082(11) 0.57986(10) 0.60571(10) 0.0257(4) Uani 1 1 d . . . . .
H14A H 0.458511 0.531557 0.571862 0.031 Uiso 1 1 calc R . . . .
H14B H 0.494994 0.579544 0.647980 0.031 Uiso 1 1 calc R . . . .
C24 C 0.75905(9) 0.78599(9) 0.55762(9) 0.0196(3) Uani 1 1 d . . . . .
H24A H 0.711242 0.819381 0.538063 0.023 Uiso 1 1 calc R . . . .
H24B H 0.738702 0.754945 0.604382 0.023 Uiso 1 1 calc R . . . .
C33 C 0.89864(11) 0.61010(9) 0.71638(9) 0.0225(3) Uani 1 1 d . . . . .
H33A H 0.935204 0.567216 0.738869 0.027 Uiso 1 1 calc R . . . .
H33B H 0.844070 0.610311 0.745847 0.027 Uiso 1 1 calc R . . . .
C35 C 0.92089(11) 0.72979(11) 0.80516(9) 0.0260(4) Uani 1 1 d . . . . .
H35A H 0.951481 0.780735 0.811419 0.039 Uiso 1 1 calc GR . . . .
H35B H 0.937508 0.692864 0.848130 0.039 Uiso 1 1 calc GR . . . .
H35C H 0.859531 0.739669 0.807840 0.039 Uiso 1 1 calc GR . . . .
C30 C 0.75148(11) 0.96859(10) 0.58634(11) 0.0284(4) Uani 1 1 d . . . . .
H30A H 0.702504 0.950293 0.554917 0.043 Uiso 1 1 calc GR . . . .
H30B H 0.758954 1.026615 0.579027 0.043 Uiso 1 1 calc GR . . . .
H30C H 0.741724 0.956992 0.643091 0.043 Uiso 1 1 calc GR . . . .
C9 C 0.40553(11) 0.85041(11) 0.46627(10) 0.0295(4) Uani 1 1 d . . . . .
H9A H 0.447440 0.812960 0.444099 0.044 Uiso 1 1 calc GR . . . .
H9B H 0.408183 0.901449 0.437078 0.044 Uiso 1 1 calc GR . . . .
H9C H 0.348457 0.827359 0.460954 0.044 Uiso 1 1 calc GR . . . .
C31 C 0.83814(11) 0.93077(10) 0.46707(10) 0.0273(4) Uani 1 1 d . . . . .
H31A H 0.887756 0.900348 0.448627 0.041 Uiso 1 1 calc GR . . . .
H31B H 0.844318 0.987302 0.451610 0.041 Uiso 1 1 calc GR . . . .
H31C H 0.786569 0.908596 0.442579 0.041 Uiso 1 1 calc GR . . . .
C37 C 0.79459(12) 0.55940(10) 0.61068(11) 0.0299(4) Uani 1 1 d . . . . .
H37A H 0.751062 0.593697 0.635023 0.045 Uiso 1 1 calc GR . . . .
H37B H 0.791298 0.505333 0.633784 0.045 Uiso 1 1 calc GR . . . .
H37C H 0.785031 0.556353 0.552788 0.045 Uiso 1 1 calc GR . . . .
C7 C 0.36720(11) 0.93293(9) 0.58700(10) 0.0262(4) Uani 1 1 d . . . . .
H7A H 0.394785 0.985860 0.579237 0.031 Uiso 1 1 calc R . . . .
H7B H 0.312249 0.933052 0.558039 0.031 Uiso 1 1 calc R . . . .
C38 C 0.95058(13) 0.54152(10) 0.58759(12) 0.0340(4) Uani 1 1 d . . . . .
H38A H 0.938138 0.536151 0.530357 0.051 Uiso 1 1 calc GR . . . .
H38B H 0.949978 0.488273 0.612699 0.051 Uiso 1 1 calc GR . . . .
H38C H 1.006782 0.565988 0.594602 0.051 Uiso 1 1 calc GR . . . .
C19 C 0.36416(13) 0.55166(10) 0.73031(11) 0.0326(4) Uani 1 1 d . . . . .
H19A H 0.404999 0.584295 0.760478 0.049 Uiso 1 1 calc GR . . . .
H19B H 0.381314 0.495059 0.732424 0.049 Uiso 1 1 calc GR . . . .
H19C H 0.307472 0.557624 0.753874 0.049 Uiso 1 1 calc GR . . . .
C36 C 1.04012(11) 0.68366(11) 0.71633(11) 0.0270(4) Uani 1 1 d . . . . .
H36A H 1.053916 0.662745 0.663074 0.041 Uiso 1 1 calc GR . . . .
H36B H 1.061099 0.646324 0.757214 0.041 Uiso 1 1 calc GR . . . .
H36C H 1.067135 0.736246 0.723630 0.041 Uiso 1 1 calc GR . . . .
C10 C 0.51957(11) 0.88824(11) 0.56427(13) 0.0349(4) Uani 1 1 d . . . . .
H10A H 0.534431 0.889180 0.621236 0.052 Uiso 1 1 calc GR . . . .
H10B H 0.529213 0.941558 0.541038 0.052 Uiso 1 1 calc GR . . . .
H10C H 0.555076 0.848611 0.536615 0.052 Uiso 1 1 calc GR . . . .
C17 C 0.42503(12) 0.64195(11) 0.46869(10) 0.0312(4) Uani 1 1 d . . . . .
H17A H 0.364260 0.629100 0.470706 0.047 Uiso 1 1 calc GR . . . .
H17B H 0.456038 0.596942 0.444619 0.047 Uiso 1 1 calc GR . . . .
H17C H 0.433613 0.690425 0.436357 0.047 Uiso 1 1 calc GR . . . .
C16 C 0.55152(11) 0.68313(11) 0.55085(11) 0.0295(4) Uani 1 1 d . . . . .
H16A H 0.557450 0.727471 0.512646 0.044 Uiso 1 1 calc GR . . . .
H16B H 0.586834 0.637789 0.533617 0.044 Uiso 1 1 calc GR . . . .
H16C H 0.569926 0.701032 0.604001 0.044 Uiso 1 1 calc GR . . . .
C12 C 0.26106(13) 0.93480(11) 0.70065(11) 0.0349(4) Uani 1 1 d . . . . .
H12A H 0.222142 0.904577 0.666071 0.052 Uiso 1 1 calc GR . . . .
H12B H 0.249678 0.992471 0.695196 0.052 Uiso 1 1 calc GR . . . .
H12C H 0.252545 0.918549 0.756446 0.052 Uiso 1 1 calc GR . . . .
C11 C 0.41405(15) 0.96224(11) 0.73181(14) 0.0467(6) Uani 1 1 d . . . . .
H11A H 0.403259 0.946340 0.787358 0.070 Uiso 1 1 calc GR . . . .
H11B H 0.405403 1.020307 0.726141 0.070 Uiso 1 1 calc GR . . . .
H11C H 0.472747 0.948710 0.717511 0.070 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
S2 O4 1.4322(13) . ?
S2 O5 1.4382(13) . ?
S2 O6 1.4331(13) . ?
S2 C40 1.8321(16) . ?
S1 O1 1.4303(14) . ?
S1 O2 1.4287(15) . ?
S1 O3 1.4309(14) . ?
S1 C39 1.8204(16) . ?
F6 C40 1.3263(19) . ?
F5 C40 1.329(2) . ?
F2 C39 1.329(2) . ?
F4 C40 1.3284(19) . ?
F3 C39 1.322(2) . ?
F1 C39 1.3286(18) . ?
N1 C6 1.4871(19) . ?
N1 C1 1.347(2) . ?
N1 C5 1.467(2) . ?
N3 C20 1.3509(19) . ?
N3 C25 1.4877(19) . ?
N3 C24 1.4680(19) . ?
N4 C22 1.4635(18) . ?
N4 C21 1.3552(18) . ?
N4 C32 1.4849(18) . ?
N2 C2 1.349(2) . ?
N2 C13 1.4853(19) . ?
N2 C3 1.461(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.522(2) . ?
C8 C1 1.533(2) . ?
C8 C9 1.528(2) . ?
C8 C7 1.546(2) . ?
C8 C10 1.543(2) . ?
C21 C20 1.409(2) . ?
C21 C34 1.5270(19) . ?
C20 C27 1.5380(19) . ?
C27 C26 1.548(2) . ?
C27 C28 1.525(2) . ?
C27 C29 1.545(2) . ?
C25 C26 1.529(2) . ?
C25 C30 1.531(2) . ?
C25 C31 1.529(2) . ?
C6 C7 1.529(2) . ?
C6 C12 1.525(3) . ?
C6 C11 1.534(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.521(2) . ?
C4 C3 1.522(2) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.519(2) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C1 C2 1.411(2) . ?
C32 C33 1.534(2) . ?
C32 C37 1.534(2) . ?
C32 C38 1.537(2) . ?
C2 C15 1.534(2) . ?
C13 C18 1.539(2) . ?
C13 C14 1.532(3) . ?
C13 C19 1.525(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C15 C14 1.544(2) . ?
C15 C17 1.545(2) . ?
C15 C16 1.530(2) . ?
C34 C33 1.544(2) . ?
C34 C35 1.526(2) . ?
C34 C36 1.541(2) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 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
O4 S2 O5 115.06(8) . . ?
O4 S2 O6 115.18(9) . . ?
O4 S2 C40 102.95(7) . . ?
O5 S2 C40 102.94(7) . . ?
O6 S2 O5 115.09(8) . . ?
O6 S2 C40 103.04(8) . . ?
O1 S1 O3 115.07(10) . . ?
O1 S1 C39 102.94(8) . . ?
O2 S1 O1 115.30(10) . . ?
O2 S1 O3 115.28(11) . . ?
O2 S1 C39 102.30(8) . . ?
O3 S1 C39 103.25(8) . . ?
C1 N1 C6 115.43(13) . . ?
C1 N1 C5 123.80(12) . . ?
C5 N1 C6 120.58(13) . . ?
C20 N3 C25 114.97(12) . . ?
C20 N3 C24 123.55(12) . . ?
C24 N3 C25 120.99(12) . . ?
C22 N4 C32 121.54(12) . . ?
C21 N4 C22 123.70(12) . . ?
C21 N4 C32 114.63(12) . . ?
C2 N2 C13 114.90(13) . . ?
C2 N2 C3 123.68(12) . . ?
C3 N2 C13 121.32(12) . . ?
N4 C22 H22A 109.1 . . ?
N4 C22 H22B 109.1 . . ?
N4 C22 C23 112.51(13) . . ?
H22A C22 H22B 107.8 . . ?
C23 C22 H22A 109.1 . . ?
C23 C22 H22B 109.1 . . ?
F2 C39 S1 112.38(11) . . ?
F3 C39 S1 112.33(11) . . ?
F3 C39 F2 107.01(14) . . ?
F3 C39 F1 106.66(14) . . ?
F1 C39 S1 111.76(11) . . ?
F1 C39 F2 106.30(14) . . ?
C1 C8 C7 99.83(13) . . ?
C1 C8 C10 111.90(13) . . ?
C9 C8 C1 115.14(14) . . ?
C9 C8 C7 109.71(13) . . ?
C9 C8 C10 109.42(15) . . ?
C10 C8 C7 110.47(14) . . ?
N4 C21 C20 120.65(13) . . ?
N4 C21 C34 108.19(12) . . ?
C20 C21 C34 131.13(13) . . ?
N3 C20 C21 120.33(13) . . ?
N3 C20 C27 108.34(12) . . ?
C21 C20 C27 131.25(13) . . ?
F6 C40 S2 111.94(12) . . ?
F6 C40 F5 106.95(14) . . ?
F6 C40 F4 107.87(14) . . ?
F5 C40 S2 111.40(11) . . ?
F4 C40 S2 111.86(11) . . ?
F4 C40 F5 106.53(14) . . ?
C20 C27 C26 99.70(11) . . ?
C20 C27 C29 111.38(12) . . ?
C28 C27 C20 116.00(12) . . ?
C28 C27 C26 109.46(13) . . ?
C28 C27 C29 110.12(13) . . ?
C29 C27 C26 109.62(13) . . ?
N3 C25 C26 100.46(12) . . ?
N3 C25 C30 110.56(13) . . ?
N3 C25 C31 109.98(13) . . ?
C26 C25 C30 114.83(13) . . ?
C26 C25 C31 111.39(13) . . ?
C31 C25 C30 109.32(13) . . ?
N1 C6 C7 100.01(12) . . ?
N1 C6 C12 110.00(14) . . ?
N1 C6 C11 110.36(13) . . ?
C7 C6 C11 114.40(16) . . ?
C12 C6 C7 111.87(14) . . ?
C12 C6 C11 109.81(15) . . ?
H4A C4 H4B 108.3 . . ?
C5 C4 H4A 109.9 . . ?
C5 C4 H4B 109.9 . . ?
C5 C4 C3 108.88(13) . . ?
C3 C4 H4A 109.9 . . ?
C3 C4 H4B 109.9 . . ?
C27 C26 H26A 110.2 . . ?
C27 C26 H26B 110.2 . . ?
C25 C26 C27 107.56(12) . . ?
C25 C26 H26A 110.2 . . ?
C25 C26 H26B 110.2 . . ?
H26A C26 H26B 108.5 . . ?
C22 C23 H23A 109.9 . . ?
C22 C23 H23B 109.9 . . ?
H23A C23 H23B 108.3 . . ?
C24 C23 C22 109.10(12) . . ?
C24 C23 H23A 109.9 . . ?
C24 C23 H23B 109.9 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N1 C1 C8 108.35(13) . . ?
N1 C1 C2 119.78(13) . . ?
C2 C1 C8 131.76(14) . . ?
N4 C32 C33 100.61(12) . . ?
N4 C32 C37 109.33(13) . . ?
N4 C32 C38 111.58(13) . . ?
C33 C32 C37 112.43(13) . . ?
C33 C32 C38 113.58(14) . . ?
C37 C32 C38 109.07(14) . . ?
N2 C2 C1 120.42(13) . . ?
N2 C2 C15 108.38(12) . . ?
C1 C2 C15 131.10(13) . . ?
N2 C13 C18 110.88(13) . . ?
N2 C13 C14 100.48(12) . . ?
N2 C13 C19 109.33(13) . . ?
C14 C13 C18 113.80(15) . . ?
C19 C13 C18 110.00(14) . . ?
C19 C13 C14 111.95(14) . . ?
N1 C5 C4 112.03(13) . . ?
N1 C5 H5A 109.2 . . ?
N1 C5 H5B 109.2 . . ?
C4 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
N2 C3 C4 112.16(13) . . ?
N2 C3 H3A 109.2 . . ?
N2 C3 H3B 109.2 . . ?
C4 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C2 C15 C14 99.76(12) . . ?
C2 C15 C17 111.35(13) . . ?
C14 C15 C17 110.87(14) . . ?
C16 C15 C2 115.47(13) . . ?
C16 C15 C14 109.53(13) . . ?
C16 C15 C17 109.50(14) . . ?
C21 C34 C33 99.88(12) . . ?
C21 C34 C36 110.63(13) . . ?
C35 C34 C21 115.67(13) . . ?
C35 C34 C33 109.49(13) . . ?
C35 C34 C36 110.00(13) . . ?
C36 C34 C33 110.78(13) . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C13 C14 C15 107.52(13) . . ?
C13 C14 H14A 110.2 . . ?
C13 C14 H14B 110.2 . . ?
C15 C14 H14A 110.2 . . ?
C15 C14 H14B 110.2 . . ?
H14A C14 H14B 108.5 . . ?
N3 C24 C23 112.24(13) . . ?
N3 C24 H24A 109.2 . . ?
N3 C24 H24B 109.2 . . ?
C23 C24 H24A 109.2 . . ?
C23 C24 H24B 109.2 . . ?
H24A C24 H24B 107.9 . . ?
C32 C33 C34 107.50(12) . . ?
C32 C33 H33A 110.2 . . ?
C32 C33 H33B 110.2 . . ?
C34 C33 H33A 110.2 . . ?
C34 C33 H33B 110.2 . . ?
H33A C33 H33B 108.5 . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C25 C30 H30A 109.5 . . ?
C25 C30 H30B 109.5 . . ?
C25 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C25 C31 H31A 109.5 . . ?
C25 C31 H31B 109.5 . . ?
C25 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C32 C37 H37A 109.5 . . ?
C32 C37 H37B 109.5 . . ?
C32 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C8 C7 H7A 110.1 . . ?
C8 C7 H7B 110.1 . . ?
C6 C7 C8 107.82(12) . . ?
C6 C7 H7A 110.1 . . ?
C6 C7 H7B 110.1 . . ?
H7A C7 H7B 108.5 . . ?
C32 C38 H38A 109.5 . . ?
C32 C38 H38B 109.5 . . ?
C32 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C13 C19 H19A 109.5 . . ?
C13 C19 H19B 109.5 . . ?
C13 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C34 C36 H36A 109.5 . . ?
C34 C36 H36B 109.5 . . ?
C34 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C6 C12 H12A 109.5 . . ?
C6 C12 H12B 109.5 . . ?
C6 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

_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
;
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.8033(6)
2 0.1967(6)

####################################################################### 
# 
# 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_AJ0063
_audit_block_doi                 10.5517/ccdc.csd.cc245rwz
_database_code_depnum_ccdc_archive 'CCDC 1971751'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D0CC07385G 2021
loop_
_audit_author_name
_audit_author_address
'HEMANT RAWAT'
;TATA INSTITUTE OF FUNDAMENTAL RESEARCH HYDERABAD
India
;
_audit_update_record             
;
2020-05-21 deposited with the CCDC.	2021-05-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H34 N2, 2(C F3 O3 S)'
_chemical_formula_sum            'C20 H34 F6 N2 O6 S2'
_chemical_formula_weight         576.61

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.2198(6)
_cell_length_b                   24.3160(12)
_cell_length_c                   11.2287(6)
_cell_angle_alpha                90
_cell_angle_beta                 104.852(6)
_cell_angle_gamma                90
_cell_volume                     2697.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    8165
_cell_measurement_theta_min      3.2510
_cell_measurement_theta_max      29.1350

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_F_000             1208
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.276
_shelx_estimated_absorpt_T_min   0.939
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.89119
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25848
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.516
_diffrn_reflns_theta_max         26.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5580
_reflns_number_gt                4772
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0669P)²+2.9217P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5580
_refine_ls_number_parameters     446
_refine_ls_number_restraints     421
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0547
_refine_ls_wR_factor_ref         0.1447
_refine_ls_wR_factor_gt          0.1388
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.115
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4904(2) 0.29111(8) 0.37463(19) 0.0324(4) Uani 1 1 d . . . . .
N2 N 0.71307(17) 0.41312(7) 0.36637(16) 0.0246(4) Uani 1 1 d . . . . .
C1 C 0.5321(2) 0.24452(9) 0.3506(2) 0.0312(5) Uani 1 1 d . . . . .
H1 H 0.605028 0.240222 0.313204 0.037 Uiso 1 1 calc R U . . .
C2 C 0.4584(2) 0.19697(9) 0.3854(2) 0.0290(5) Uani 1 1 d . . . . .
C3 C 0.3475(11) 0.2257(5) 0.4369(13) 0.044(2) Uani 0.470(15) 1 d . . P A 1
H3A H 0.339865 0.207671 0.513891 0.052 Uiso 0.470(15) 1 calc R U P A 1
H3B H 0.258406 0.224099 0.375971 0.052 Uiso 0.470(15) 1 calc R U P A 1
C4 C 0.3969(11) 0.2889(4) 0.4632(11) 0.039(2) Uani 0.470(15) 1 d . . P A 1
C5 C 0.4569(17) 0.3199(3) 0.5824(11) 0.073(4) Uani 0.470(15) 1 d . . P A 1
H5A H 0.462290 0.359189 0.564399 0.110 Uiso 0.470(15) 1 calc R U P A 1
H5B H 0.547898 0.305852 0.620421 0.110 Uiso 0.470(15) 1 calc R U P A 1
H5C H 0.399266 0.314769 0.639056 0.110 Uiso 0.470(15) 1 calc R U P A 1
C6 C 0.2641(9) 0.3131(4) 0.3902(15) 0.074(4) Uani 0.470(15) 1 d . . P A 1
H6A H 0.193294 0.305273 0.432353 0.111 Uiso 0.470(15) 1 calc R U P A 1
H6B H 0.239279 0.296768 0.307669 0.111 Uiso 0.470(15) 1 calc R U P A 1
H6C H 0.273859 0.352997 0.383264 0.111 Uiso 0.470(15) 1 calc R U P A 1
C3' C 0.3944(10) 0.2251(4) 0.4795(9) 0.0355(17) Uani 0.530(15) 1 d . . P A 2
H3C H 0.459865 0.229241 0.560877 0.043 Uiso 0.530(15) 1 calc R U P A 2
H3D H 0.313222 0.205183 0.489142 0.043 Uiso 0.530(15) 1 calc R U P A 2
C4' C 0.3539(9) 0.2865(3) 0.4079(10) 0.0349(17) Uani 0.530(15) 1 d . . P A 2
C5' C 0.3631(12) 0.3232(3) 0.5170(9) 0.062(3) Uani 0.530(15) 1 d . . P A 2
H5D H 0.381752 0.361000 0.495639 0.093 Uiso 0.530(15) 1 calc R U P A 2
H5E H 0.436268 0.310486 0.586114 0.093 Uiso 0.530(15) 1 calc R U P A 2
H5F H 0.277166 0.322267 0.540603 0.093 Uiso 0.530(15) 1 calc R U P A 2
C6' C 0.2372(7) 0.3035(3) 0.3009(12) 0.063(3) Uani 0.530(15) 1 d . . P A 2
H6D H 0.151233 0.295777 0.321129 0.095 Uiso 0.530(15) 1 calc R U P A 2
H6E H 0.241384 0.282813 0.227120 0.095 Uiso 0.530(15) 1 calc R U P A 2
H6F H 0.243512 0.342969 0.285402 0.095 Uiso 0.530(15) 1 calc R U P A 2
C7 C 0.3737(5) 0.17022(15) 0.2674(3) 0.0877(15) Uani 1 1 d . . . . .
H7A H 0.314293 0.197873 0.217540 0.132 Uiso 1 1 calc R U . . .
H7B H 0.318759 0.140608 0.288715 0.132 Uiso 1 1 calc R U . . .
H7C H 0.433953 0.155044 0.220378 0.132 Uiso 1 1 calc R U . . .
C8 C 0.5519(3) 0.15369(12) 0.4586(4) 0.0624(10) Uani 1 1 d . . . . .
H8A H 0.607093 0.137855 0.407551 0.094 Uiso 1 1 calc R U . . .
H8B H 0.498068 0.124624 0.483566 0.094 Uiso 1 1 calc R U . . .
H8C H 0.611216 0.170605 0.532083 0.094 Uiso 1 1 calc R U . . .
C9 C 0.5370(3) 0.34370(9) 0.3339(2) 0.0357(5) Uani 1 1 d . . . . .
H9A H 0.463781 0.371306 0.323971 0.043 Uiso 1 1 calc R U . . .
H9B H 0.555891 0.338347 0.252462 0.043 Uiso 1 1 calc R U . . .
C10 C 0.6644(3) 0.36572(9) 0.4247(2) 0.0344(5) Uani 1 1 d . . . . .
H10A H 0.643309 0.377207 0.502285 0.041 Uiso 1 1 calc R U . . .
H10B H 0.734873 0.336785 0.444138 0.041 Uiso 1 1 calc R U . . .
C11 C 0.8411(2) 0.41189(10) 0.3209(2) 0.0322(5) Uani 1 1 d . . . . .
C12 C 0.8467(2) 0.47182(11) 0.2777(3) 0.0404(6) Uani 1 1 d . . . . .
H12A H 0.922898 0.491489 0.333751 0.048 Uiso 1 1 calc R U . . .
H12B H 0.860531 0.472559 0.193633 0.048 Uiso 1 1 calc R U . . .
C13 C 0.7119(2) 0.49976(8) 0.27832(19) 0.0239(4) Uani 1 1 d . . . . .
C14 C 0.6509(2) 0.45926(8) 0.34778(19) 0.0236(4) Uani 1 1 d . . . . .
H14 H 0.572685 0.466994 0.375835 0.028 Uiso 1 1 calc R U . . .
C15 C 0.7304(3) 0.55548(9) 0.3438(2) 0.0345(5) Uani 1 1 d . . . . .
H15A H 0.780520 0.550470 0.429980 0.052 Uiso 1 1 calc R U . . .
H15B H 0.641475 0.571472 0.340262 0.052 Uiso 1 1 calc R U . . .
H15C H 0.781027 0.580190 0.302936 0.052 Uiso 1 1 calc R U . . .
C16 C 0.6159(3) 0.50592(11) 0.1493(2) 0.0361(5) Uani 1 1 d . . . . .
H16A H 0.655806 0.531168 0.100295 0.054 Uiso 1 1 calc R U . . .
H16B H 0.528896 0.520616 0.156275 0.054 Uiso 1 1 calc R U . . .
H16C H 0.601678 0.469908 0.108797 0.054 Uiso 1 1 calc R U . . .
C17 C 0.8237(3) 0.36969(12) 0.2180(3) 0.0445(6) Uani 1 1 d . . . . .
H17A H 0.810848 0.333151 0.250112 0.067 Uiso 1 1 calc R U . . .
H17B H 0.904559 0.369488 0.186394 0.067 Uiso 1 1 calc R U . . .
H17C H 0.744367 0.379242 0.151360 0.067 Uiso 1 1 calc R U . . .
C18 C 0.9608(2) 0.39800(12) 0.4289(3) 0.0440(7) Uani 1 1 d . . . . .
H18A H 0.961718 0.422971 0.497633 0.066 Uiso 1 1 calc R U . . .
H18B H 1.045174 0.402117 0.403601 0.066 Uiso 1 1 calc R U . . .
H18C H 0.952428 0.359983 0.454970 0.066 Uiso 1 1 calc R U . . .
S1 S 0.9466(2) 0.23130(9) 0.4961(2) 0.0307(4) Uani 0.684(4) 1 d D U P B 1
O1 O 1.0700(8) 0.2361(4) 0.5892(10) 0.053(2) Uani 0.684(4) 1 d D U P B 1
O2 O 0.9460(7) 0.26106(16) 0.3868(4) 0.118(2) Uani 0.684(4) 1 d D U P B 1
O3 O 0.8322(5) 0.2361(3) 0.5405(8) 0.125(3) Uani 0.684(4) 1 d D U P B 1
F1 F 1.0467(7) 0.1514(3) 0.3930(7) 0.101(2) Uani 0.684(4) 1 d D U P B 1
F2 F 0.9371(5) 0.12647(11) 0.5324(3) 0.0970(15) Uani 0.684(4) 1 d D U P B 1
F3 F 0.8347(5) 0.14972(18) 0.3543(5) 0.0543(11) Uani 0.684(4) 1 d D U P B 1
C19 C 0.9425(4) 0.16076(15) 0.4424(3) 0.0325(8) Uani 0.684(4) 1 d D U P B 1
S1' S 0.9333(7) 0.2195(3) 0.5212(6) 0.0470(13) Uani 0.316(4) 1 d D U P B 2
O1' O 0.8959(11) 0.1758(6) 0.5852(9) 0.113(4) Uani 0.316(4) 1 d D U P B 2
O2' O 0.8239(11) 0.2518(4) 0.4699(12) 0.090(4) Uani 0.316(4) 1 d D U P B 2
O3' O 1.0626(16) 0.2434(10) 0.573(2) 0.053(4) Uani 0.316(4) 1 d D U P B 2
F1' F 1.0058(10) 0.2232(5) 0.3189(8) 0.140(5) Uani 0.316(4) 1 d D U P B 2
F2' F 1.0479(16) 0.1426(6) 0.4371(17) 0.121(7) Uani 0.316(4) 1 d D U P B 2
F3' F 0.8439(13) 0.1670(6) 0.3216(13) 0.105(5) Uani 0.316(4) 1 d D U P B 2
C19' C 0.9664(11) 0.1853(5) 0.3873(11) 0.083(4) Uani 0.316(4) 1 d D U P B 2
S2 S 0.78204(5) -0.00574(2) 0.82896(5) 0.02493(15) Uani 1 1 d D . . . .
O4 O 0.84940(19) 0.04499(8) 0.87324(19) 0.0478(5) Uani 1 1 d D . . . .
O5 O 0.87164(19) -0.04956(8) 0.81673(19) 0.0483(5) Uani 1 1 d D . . . .
O6 O 0.67484(17) -0.02078(8) 0.88352(16) 0.0393(4) Uani 1 1 d D . . . .
F4 F 0.7814(2) 0.02864(11) 0.60906(18) 0.0809(7) Uani 1 1 d D . . . .
F5 F 0.60775(17) 0.05249(8) 0.66758(18) 0.0628(5) Uani 1 1 d D . . . .
F6 F 0.6231(3) -0.03037(10) 0.6138(2) 0.1053(10) Uani 1 1 d D . . . .
C20 C 0.6941(3) 0.01109(12) 0.6709(2) 0.0421(6) Uani 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.264(3) . ?
N1 C9 1.478(3) . ?
N1 C4' 1.538(7) . ?
N1 C4 1.546(9) . ?
N2 C14 1.280(3) . ?
N2 C10 1.474(3) . ?
N2 C11 1.522(3) . ?
C1 C2 1.486(3) . ?
C2 C8 1.515(4) . ?
C2 C7 1.529(4) . ?
C2 C3' 1.538(10) . ?
C2 C3 1.563(12) . ?
C3 C4 1.620(16) . ?
C4 C6 1.513(12) . ?
C4 C5 1.522(12) . ?
C3' C4' 1.696(14) . ?
C4' C5' 1.500(9) . ?
C4' C6' 1.517(10) . ?
C9 C10 1.531(3) . ?
C11 C17 1.521(3) . ?
C11 C18 1.523(3) . ?
C11 C12 1.541(4) . ?
C12 C13 1.537(3) . ?
C13 C14 1.489(3) . ?
C13 C15 1.530(3) . ?
C13 C16 1.535(3) . ?
S1 O3 1.388(5) . ?
S1 O1 1.422(7) . ?
S1 O2 1.423(5) . ?
S1 C19 1.815(4) . ?
F1 C19 1.340(6) . ?
F2 C19 1.323(5) . ?
F3 C19 1.306(5) . ?
S1' O2' 1.366(9) . ?
S1' O1' 1.392(9) . ?
S1' O3' 1.424(13) . ?
S1' C19' 1.825(11) . ?
F1' C19' 1.327(13) . ?
F2' C19' 1.359(14) . ?
F3' C19' 1.354(12) . ?
S2 O6 1.4329(16) . ?
S2 O5 1.4343(19) . ?
S2 O4 1.4379(19) . ?
S2 C20 1.818(3) . ?
F4 C20 1.333(3) . ?
F5 C20 1.333(3) . ?
F6 C20 1.310(4) . ?

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
C1 N1 C9 123.8(2) . . ?
C1 N1 C4' 111.3(3) . . ?
C9 N1 C4' 121.5(3) . . ?
C1 N1 C4 113.8(4) . . ?
C9 N1 C4 122.1(4) . . ?
C14 N2 C10 123.25(19) . . ?
C14 N2 C11 113.33(18) . . ?
C10 N2 C11 123.41(18) . . ?
N1 C1 C2 114.8(2) . . ?
C1 C2 C8 113.0(2) . . ?
C1 C2 C7 108.4(2) . . ?
C8 C2 C7 108.2(3) . . ?
C1 C2 C3' 99.7(4) . . ?
C8 C2 C3' 104.9(4) . . ?
C7 C2 C3' 122.6(5) . . ?
C1 C2 C3 102.4(4) . . ?
C8 C2 C3 121.8(5) . . ?
C7 C2 C3 102.0(6) . . ?
C2 C3 C4 105.7(7) . . ?
C6 C4 C5 112.7(8) . . ?
C6 C4 N1 104.7(7) . . ?
C5 C4 N1 111.8(7) . . ?
C6 C4 C3 94.4(9) . . ?
C5 C4 C3 131.8(9) . . ?
N1 C4 C3 97.5(7) . . ?
C2 C3' C4' 99.3(6) . . ?
C5' C4' C6' 110.9(6) . . ?
C5' C4' N1 106.5(6) . . ?
C6' C4' N1 111.4(6) . . ?
C5' C4' C3' 100.4(7) . . ?
C6' C4' C3' 131.5(8) . . ?
N1 C4' C3' 93.0(6) . . ?
N1 C9 C10 112.5(2) . . ?
N2 C10 C9 107.68(18) . . ?
C17 C11 N2 108.94(19) . . ?
C17 C11 C18 111.6(2) . . ?
N2 C11 C18 108.7(2) . . ?
C17 C11 C12 113.9(2) . . ?
N2 C11 C12 101.04(17) . . ?
C18 C11 C12 111.9(2) . . ?
C13 C12 C11 108.11(18) . . ?
C14 C13 C15 110.54(17) . . ?
C14 C13 C16 107.86(17) . . ?
C15 C13 C16 109.71(19) . . ?
C14 C13 C12 101.90(18) . . ?
C15 C13 C12 113.16(19) . . ?
C16 C13 C12 113.3(2) . . ?
N2 C14 C13 114.08(18) . . ?
O3 S1 O1 113.5(6) . . ?
O3 S1 O2 116.7(5) . . ?
O1 S1 O2 113.5(6) . . ?
O3 S1 C19 104.4(3) . . ?
O1 S1 C19 105.2(5) . . ?
O2 S1 C19 101.5(3) . . ?
F3 C19 F2 104.9(4) . . ?
F3 C19 F1 104.9(5) . . ?
F2 C19 F1 113.8(5) . . ?
F3 C19 S1 112.9(3) . . ?
F2 C19 S1 110.1(3) . . ?
F1 C19 S1 110.1(4) . . ?
O2' S1' O1' 110.7(9) . . ?
O2' S1' O3' 120.8(13) . . ?
O1' S1' O3' 116.7(12) . . ?
O2' S1' C19' 102.7(8) . . ?
O1' S1' C19' 102.1(8) . . ?
O3' S1' C19' 100.0(11) . . ?
F1' C19' F3' 106.7(11) . . ?
F1' C19' F2' 121.7(13) . . ?
F3' C19' F2' 110.9(12) . . ?
F1' C19' S1' 107.9(8) . . ?
F3' C19' S1' 104.9(10) . . ?
F2' C19' S1' 103.5(10) . . ?
O6 S2 O5 115.36(12) . . ?
O6 S2 O4 114.95(12) . . ?
O5 S2 O4 114.18(12) . . ?
O6 S2 C20 103.54(11) . . ?
O5 S2 C20 103.98(12) . . ?
O4 S2 C20 102.55(13) . . ?
F6 C20 F4 110.6(3) . . ?
F6 C20 F5 106.7(3) . . ?
F4 C20 F5 105.7(2) . . ?
F6 C20 S2 112.2(2) . . ?
F4 C20 S2 110.58(19) . . ?
F5 C20 S2 110.81(19) . . ?

_refine_diff_density_max         0.706
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.061

####################################################################### 
# 
# 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_AJ0779r
_audit_block_doi                 10.5517/ccdc.csd.cc245s37
_database_code_depnum_ccdc_archive 'CCDC 1971758'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D0CC07385G 2021
_audit_update_record             
;
2021-04-01 deposited with the CCDC.	2021-05-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H38 N2, 2(C F3 O3 S)'
_chemical_formula_sum            'C24 H38 F6 N2 O6 S2'
_chemical_formula_weight         628.68

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   16.0963(7)
_cell_length_b                   12.0415(5)
_cell_length_c                   14.8878(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.041(4)
_cell_angle_gamma                90
_cell_volume                     2883.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    13012
_cell_measurement_theta_min      3.3000
_cell_measurement_theta_max      28.0060

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_F_000             1320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.265
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.76315
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6920
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.493
_diffrn_reflns_theta_max         28.876
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.915
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             6920
_reflns_number_gt                5336
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0671P)²+7.8877P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6920
_refine_ls_number_parameters     571
_refine_ls_number_restraints     1720
_refine_ls_R_factor_all          0.1050
_refine_ls_R_factor_gt           0.0869
_refine_ls_wR_factor_ref         0.2316
_refine_ls_wR_factor_gt          0.2236
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.18613(18) 0.4226(2) 0.6067(2) 0.0208(6) Uani 1 1 d D . . . .
N2 N 0.32056(19) 0.5671(3) 0.6167(2) 0.0221(6) Uani 1 1 d D . . . .
C1 C 0.2197(2) 0.4472(3) 0.6851(3) 0.0222(7) Uani 1 1 d . . . . .
C2 C 0.2926(2) 0.5254(3) 0.6900(3) 0.0244(8) Uani 1 1 d . . . . .
C5 C 0.1148(2) 0.3382(3) 0.6120(3) 0.0261(8) Uani 1 1 d . . . . .
C6 C 0.1280(3) 0.2998(4) 0.7088(3) 0.0315(9) Uani 1 1 d . . . . .
H6A H 0.160241 0.229758 0.710809 0.038 Uiso 1 1 calc R U . . .
H6B H 0.073648 0.285970 0.735954 0.038 Uiso 1 1 calc R U . . .
C7 C 0.1753(3) 0.3908(4) 0.7613(3) 0.0295(9) Uani 1 1 d . . . . .
C8 C 0.2300(3) 0.3332(4) 0.8333(3) 0.0403(11) Uani 1 1 d . . . . .
H8A H 0.273744 0.290851 0.804473 0.060 Uiso 1 1 calc R U . . .
H8B H 0.195961 0.282690 0.868171 0.060 Uiso 1 1 calc R U . . .
H8C H 0.255490 0.389112 0.873409 0.060 Uiso 1 1 calc R U . . .
C9 C 0.1145(3) 0.4743(4) 0.8038(3) 0.0420(11) Uani 1 1 d . . . . .
H9A H 0.146002 0.537242 0.829255 0.063 Uiso 1 1 calc R U . . .
H9B H 0.084588 0.437233 0.851555 0.063 Uiso 1 1 calc R U . . .
H9C H 0.074632 0.501153 0.757543 0.063 Uiso 1 1 calc R U . . .
C10 C 0.0321(2) 0.3988(4) 0.5933(3) 0.0321(9) Uani 1 1 d . . . . .
H10A H 0.033313 0.470775 0.624058 0.048 Uiso 1 1 calc R U . . .
H10B H -0.013616 0.353897 0.615381 0.048 Uiso 1 1 calc R U . . .
H10C H 0.023866 0.410543 0.528419 0.048 Uiso 1 1 calc R U . . .
C11 C 0.1253(3) 0.2404(4) 0.5484(3) 0.0346(10) Uani 1 1 d . . . . .
H11A H 0.102583 0.259915 0.488542 0.052 Uiso 1 1 calc R U . . .
H11B H 0.095653 0.175751 0.571128 0.052 Uiso 1 1 calc R U . . .
H11C H 0.184530 0.222688 0.544690 0.052 Uiso 1 1 calc R U . . .
C12 C 0.3945(2) 0.6464(3) 0.6335(3) 0.0286(9) Uani 1 1 d . . . . .
C13 C 0.3891(3) 0.6624(4) 0.7341(3) 0.0387(10) Uani 1 1 d . . . . .
H13A H 0.358221 0.731417 0.746651 0.046 Uiso 1 1 calc R U . . .
H13B H 0.445677 0.668955 0.761967 0.046 Uiso 1 1 calc R U . . .
C14 C 0.3442(3) 0.5622(4) 0.7735(3) 0.0340(10) Uani 1 1 d . . . . .
C15 C 0.2946(4) 0.6047(5) 0.8531(3) 0.0481(13) Uani 1 1 d . . . . .
H15A H 0.252116 0.657328 0.831204 0.072 Uiso 1 1 calc R U . . .
H15B H 0.332376 0.641865 0.896568 0.072 Uiso 1 1 calc R U . . .
H15C H 0.267752 0.541876 0.882298 0.072 Uiso 1 1 calc R U . . .
C16 C 0.4055(3) 0.4699(5) 0.8041(4) 0.0451(12) Uani 1 1 d . . . . .
H16A H 0.374363 0.406533 0.826968 0.068 Uiso 1 1 calc R U . . .
H16B H 0.443180 0.498497 0.851826 0.068 Uiso 1 1 calc R U . . .
H16C H 0.437828 0.446005 0.753037 0.068 Uiso 1 1 calc R U . . .
C17 C 0.4735(3) 0.5887(4) 0.6046(4) 0.0403(11) Uani 1 1 d . . . . .
H17A H 0.477086 0.514792 0.632130 0.060 Uiso 1 1 calc R U . . .
H17B H 0.522014 0.632762 0.624171 0.060 Uiso 1 1 calc R U . . .
H17C H 0.472166 0.581334 0.539044 0.060 Uiso 1 1 calc R U . . .
C18 C 0.3815(3) 0.7580(4) 0.5865(4) 0.0387(11) Uani 1 1 d . . . . .
H18A H 0.395740 0.751187 0.523245 0.058 Uiso 1 1 calc R U . . .
H18B H 0.417163 0.814147 0.615862 0.058 Uiso 1 1 calc R U . . .
H18C H 0.323152 0.780423 0.590050 0.058 Uiso 1 1 calc R U . . .
C3 C 0.2761(5) 0.5570(6) 0.5269(5) 0.0236(16) Uani 0.667(12) 1 d D U P A 1
H3 H 0.237193 0.621554 0.521787 0.028 Uiso 0.667(12) 1 calc R U P A 1
C4 C 0.2225(4) 0.4527(6) 0.5199(5) 0.0238(15) Uani 0.667(12) 1 d D U P A 1
H4 H 0.259507 0.390142 0.502702 0.029 Uiso 0.667(12) 1 calc R U P A 1
C19 C 0.3290(5) 0.5601(8) 0.4432(5) 0.0309(19) Uani 0.667(12) 1 d D U P A 1
H19A H 0.368338 0.623208 0.447225 0.037 Uiso 0.667(12) 1 calc R U P A 1
H19B H 0.361471 0.490588 0.438885 0.037 Uiso 0.667(12) 1 calc R U P A 1
C20 C 0.2718(7) 0.5728(9) 0.3610(7) 0.038(2) Uani 0.667(12) 1 d D U P A 1
H20A H 0.305336 0.571088 0.306545 0.046 Uiso 0.667(12) 1 calc R U P A 1
H20B H 0.244013 0.646062 0.363181 0.046 Uiso 0.667(12) 1 calc R U P A 1
C21 C 0.2060(7) 0.4824(10) 0.3538(7) 0.035(3) Uani 0.667(12) 1 d D U P A 1
H21A H 0.232809 0.410708 0.340044 0.041 Uiso 0.667(12) 1 calc R U P A 1
H21B H 0.165981 0.500153 0.303828 0.041 Uiso 0.667(12) 1 calc R U P A 1
C22 C 0.1598(5) 0.4718(8) 0.4409(6) 0.032(2) Uani 0.667(12) 1 d D U P A 1
H22A H 0.120384 0.408766 0.436359 0.038 Uiso 0.667(12) 1 calc R U P A 1
H22B H 0.127537 0.540396 0.451261 0.038 Uiso 0.667(12) 1 calc R U P A 1
C3' C 0.2958(9) 0.5210(13) 0.5306(10) 0.026(3) Uani 0.333(12) 1 d D U P A 2
H3' H 0.327009 0.450211 0.522057 0.031 Uiso 0.333(12) 1 calc R U P A 2
C4' C 0.2033(9) 0.4949(14) 0.5279(9) 0.028(3) Uani 0.333(12) 1 d D U P A 2
H4' H 0.171149 0.565642 0.532514 0.034 Uiso 0.333(12) 1 calc R U P A 2
C19' C 0.3136(11) 0.5987(13) 0.4524(11) 0.032(4) Uani 0.333(12) 1 d D U P A 2
H19C H 0.280883 0.667814 0.458154 0.039 Uiso 0.333(12) 1 calc R U P A 2
H19D H 0.373247 0.618703 0.454377 0.039 Uiso 0.333(12) 1 calc R U P A 2
C20' C 0.2911(13) 0.543(2) 0.3637(12) 0.045(5) Uani 0.333(12) 1 d D U P A 2
H20C H 0.325190 0.475634 0.356920 0.054 Uiso 0.333(12) 1 calc R U P A 2
H20D H 0.303217 0.594452 0.313702 0.054 Uiso 0.333(12) 1 calc R U P A 2
C21' C 0.1995(14) 0.513(2) 0.3591(13) 0.036(5) Uani 0.333(12) 1 d D U P A 2
H21C H 0.185992 0.473300 0.302080 0.044 Uiso 0.333(12) 1 calc R U P A 2
H21D H 0.165220 0.580736 0.360915 0.044 Uiso 0.333(12) 1 calc R U P A 2
C22' C 0.1803(13) 0.4382(15) 0.4383(11) 0.039(4) Uani 0.333(12) 1 d D U P A 2
H22C H 0.211786 0.367881 0.433796 0.047 Uiso 0.333(12) 1 calc R U P A 2
H22D H 0.120283 0.419868 0.436211 0.047 Uiso 0.333(12) 1 calc R U P A 2
S1 S 0.39739(6) 0.24446(9) 0.58038(8) 0.0284(3) Uani 0.953(3) 1 d D U P B 1
O1 O 0.4854(2) 0.2559(5) 0.5998(3) 0.0520(12) Uani 0.953(3) 1 d D U P B 1
O2 O 0.3447(3) 0.2972(3) 0.6434(3) 0.0528(11) Uani 0.953(3) 1 d D U P B 1
O3 O 0.3706(2) 0.2597(3) 0.4880(2) 0.0460(9) Uani 0.953(3) 1 d D U P B 1
C23 C 0.3778(3) 0.0985(4) 0.5996(4) 0.0475(13) Uani 0.953(3) 1 d D U P B 1
F1 F 0.3966(2) 0.0695(3) 0.6842(3) 0.0631(10) Uani 0.953(3) 1 d D U P B 1
F2 F 0.4248(3) 0.0357(3) 0.5465(3) 0.0811(14) Uani 0.953(3) 1 d D U P B 1
F3 F 0.3002(2) 0.0726(3) 0.5791(4) 0.0969(18) Uani 0.953(3) 1 d D U P B 1
S1' S 0.4058(13) 0.2379(17) 0.645(2) 0.045(5) Uani 0.047(3) 1 d D U P B 2
O1' O 0.475(3) 0.251(6) 0.588(5) 0.055(9) Uani 0.047(3) 1 d D U P B 2
O2' O 0.3522(17) 0.3272(17) 0.654(4) 0.052(9) Uani 0.047(3) 1 d D U P B 2
O3' O 0.429(4) 0.187(4) 0.731(3) 0.060(9) Uani 0.047(3) 1 d D U P B 2
C23' C 0.344(2) 0.128(3) 0.592(3) 0.050(6) Uani 0.047(3) 1 d D U P B 2
F1' F 0.308(3) 0.160(4) 0.515(3) 0.064(8) Uani 0.047(3) 1 d D U P B 2
F2' F 0.386(3) 0.034(3) 0.584(4) 0.052(8) Uani 0.047(3) 1 d D U P B 2
F3' F 0.283(2) 0.100(3) 0.645(3) 0.035(7) Uani 0.047(3) 1 d D U P B 2
S2 S 0.0968(2) 0.7517(3) 0.6597(2) 0.0327(7) Uani 0.783(13) 1 d D U P C 1
O4 O 0.0822(5) 0.8217(6) 0.7340(4) 0.0579(18) Uani 0.783(13) 1 d D U P C 1
O5 O 0.1732(4) 0.6916(7) 0.6663(5) 0.061(2) Uani 0.783(13) 1 d D U P C 1
O6 O 0.0252(5) 0.6886(7) 0.6295(7) 0.066(2) Uani 0.783(13) 1 d D U P C 1
C24 C 0.1125(4) 0.8480(6) 0.5667(6) 0.0474(16) Uani 0.783(13) 1 d D U P C 1
F4 F 0.1774(4) 0.9115(5) 0.5820(7) 0.085(2) Uani 0.783(13) 1 d D U P C 1
F5 F 0.0473(3) 0.9080(5) 0.5465(5) 0.0682(18) Uani 0.783(13) 1 d D U P C 1
F6 F 0.1266(5) 0.7918(6) 0.4914(4) 0.0808(19) Uani 0.783(13) 1 d D U P C 1
S2' S 0.0980(11) 0.7459(13) 0.6606(13) 0.052(3) Uani 0.217(13) 1 d D U P C 2
O4' O 0.0958(19) 0.787(2) 0.7505(14) 0.061(5) Uani 0.217(13) 1 d D U P C 2
O5' O 0.1574(13) 0.666(2) 0.646(2) 0.059(5) Uani 0.217(13) 1 d D U P C 2
O6' O 0.0148(12) 0.714(2) 0.629(2) 0.051(4) Uani 0.217(13) 1 d D U P C 2
C24' C 0.1253(13) 0.8635(16) 0.5923(15) 0.055(4) Uani 0.217(13) 1 d D U P C 2
F4' F 0.1575(15) 0.837(2) 0.5147(13) 0.072(4) Uani 0.217(13) 1 d D U P C 2
F5' F 0.0652(14) 0.9369(16) 0.591(2) 0.074(4) Uani 0.217(13) 1 d D U P C 2
F6' F 0.1878(14) 0.9181(19) 0.6332(18) 0.077(4) Uani 0.217(13) 1 d D U P C 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
N1 C1 1.302(5) . ?
N1 C4 1.482(8) . ?
N1 C4' 1.495(14) . ?
N1 C5 1.538(5) . ?
N2 C2 1.297(5) . ?
N2 C3' 1.440(15) . ?
N2 C3 1.498(9) . ?
N2 C12 1.539(5) . ?
C1 C2 1.504(5) . ?
C1 C7 1.523(5) . ?
C2 C14 1.536(6) . ?
C5 C6 1.522(6) . ?
C5 C11 1.524(6) . ?
C5 C10 1.535(5) . ?
C6 C7 1.533(6) . ?
C7 C8 1.529(6) . ?
C7 C9 1.554(6) . ?
C12 C13 1.515(6) . ?
C12 C17 1.524(6) . ?
C12 C18 1.527(6) . ?
C13 C14 1.535(6) . ?
C14 C15 1.540(7) . ?
C14 C16 1.544(7) . ?
C3 C4 1.525(9) . ?
C3 C19 1.535(9) . ?
C4 C22 1.541(9) . ?
C19 C20 1.513(10) . ?
C20 C21 1.519(11) . ?
C21 C22 1.523(11) . ?
C3' C4' 1.521(15) . ?
C3' C19' 1.528(15) . ?
C4' C22' 1.532(15) . ?
C19' C20' 1.512(16) . ?
C20' C21' 1.519(17) . ?
C21' C22' 1.521(16) . ?
S1 O2 1.435(4) . ?
S1 O3 1.438(4) . ?
S1 O1 1.442(4) . ?
S1 C23 1.811(5) . ?
C23 F3 1.313(6) . ?
C23 F1 1.331(6) . ?
C23 F2 1.346(7) . ?
S1' O2' 1.389(15) . ?
S1' O1' 1.427(16) . ?
S1' O3' 1.456(16) . ?
S1' C23' 1.820(16) . ?
C23' F1' 1.316(17) . ?
C23' F2' 1.319(17) . ?
C23' F3' 1.327(18) . ?
S2 O4 1.417(5) . ?
S2 O5 1.428(5) . ?
S2 O6 1.439(6) . ?
S2 C24 1.831(7) . ?
C24 F5 1.301(7) . ?
C24 F4 1.306(8) . ?
C24 F6 1.336(9) . ?
S2' O5' 1.382(14) . ?
S2' O4' 1.430(14) . ?
S2' O6' 1.456(15) . ?
S2' C24' 1.807(14) . ?
C24' F5' 1.309(15) . ?
C24' F4' 1.321(16) . ?
C24' F6' 1.331(16) . ?

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
C1 N1 C4 124.1(4) . . ?
C1 N1 C4' 119.2(6) . . ?
C1 N1 C5 113.1(3) . . ?
C4 N1 C5 121.6(4) . . ?
C4' N1 C5 125.7(6) . . ?
C2 N2 C3' 120.4(6) . . ?
C2 N2 C3 123.4(4) . . ?
C2 N2 C12 113.1(3) . . ?
C3' N2 C12 124.9(6) . . ?
C3 N2 C12 122.5(4) . . ?
N1 C1 C2 119.0(3) . . ?
N1 C1 C7 112.0(3) . . ?
C2 C1 C7 129.0(3) . . ?
N2 C2 C1 119.7(3) . . ?
N2 C2 C14 112.1(3) . . ?
C1 C2 C14 128.2(3) . . ?
C6 C5 C11 109.8(3) . . ?
C6 C5 C10 114.0(3) . . ?
C11 C5 C10 111.7(3) . . ?
C6 C5 N1 99.8(3) . . ?
C11 C5 N1 112.3(3) . . ?
C10 C5 N1 108.7(3) . . ?
C5 C6 C7 108.4(3) . . ?
C1 C7 C8 116.8(4) . . ?
C1 C7 C6 100.2(3) . . ?
C8 C7 C6 107.3(4) . . ?
C1 C7 C9 109.5(3) . . ?
C8 C7 C9 111.3(4) . . ?
C6 C7 C9 111.2(4) . . ?
C13 C12 C17 114.5(4) . . ?
C13 C12 C18 109.2(4) . . ?
C17 C12 C18 112.0(4) . . ?
C13 C12 N2 99.7(3) . . ?
C17 C12 N2 108.6(3) . . ?
C18 C12 N2 112.2(3) . . ?
C12 C13 C14 108.8(3) . . ?
C13 C14 C2 99.5(3) . . ?
C13 C14 C15 107.3(4) . . ?
C2 C14 C15 116.0(4) . . ?
C13 C14 C16 112.0(4) . . ?
C2 C14 C16 110.7(4) . . ?
C15 C14 C16 110.8(4) . . ?
N2 C3 C4 112.3(6) . . ?
N2 C3 C19 117.5(6) . . ?
C4 C3 C19 107.1(7) . . ?
N1 C4 C3 112.5(6) . . ?
N1 C4 C22 115.7(6) . . ?
C3 C4 C22 106.5(7) . . ?
C20 C19 C3 108.7(8) . . ?
C19 C20 C21 112.8(8) . . ?
C20 C21 C22 111.1(9) . . ?
C21 C22 C4 109.6(7) . . ?
N2 C3' C4' 110.1(11) . . ?
N2 C3' C19' 112.8(12) . . ?
C4' C3' C19' 108.4(13) . . ?
N1 C4' C3' 107.9(11) . . ?
N1 C4' C22' 112.2(12) . . ?
C3' C4' C22' 108.7(14) . . ?
C20' C19' C3' 110.5(14) . . ?
C19' C20' C21' 110.3(16) . . ?
C20' C21' C22' 109.5(16) . . ?
C21' C22' C4' 111.2(15) . . ?
O2 S1 O3 113.9(2) . . ?
O2 S1 O1 115.2(3) . . ?
O3 S1 O1 116.0(3) . . ?
O2 S1 C23 102.5(3) . . ?
O3 S1 C23 103.1(2) . . ?
O1 S1 C23 103.7(3) . . ?
F3 C23 F1 109.9(5) . . ?
F3 C23 F2 106.3(5) . . ?
F1 C23 F2 107.1(4) . . ?
F3 C23 S1 111.3(3) . . ?
F1 C23 S1 111.7(4) . . ?
F2 C23 S1 110.3(4) . . ?
O2' S1' O1' 118(2) . . ?
O2' S1' O3' 112(2) . . ?
O1' S1' O3' 113(2) . . ?
O2' S1' C23' 106.1(16) . . ?
O1' S1' C23' 104(2) . . ?
O3' S1' C23' 101.3(18) . . ?
F1' C23' F2' 112(2) . . ?
F1' C23' F3' 106(2) . . ?
F2' C23' F3' 103(2) . . ?
F1' C23' S1' 112(2) . . ?
F2' C23' S1' 113(2) . . ?
F3' C23' S1' 109.1(19) . . ?
O4 S2 O5 114.4(4) . . ?
O4 S2 O6 113.9(5) . . ?
O5 S2 O6 115.7(5) . . ?
O4 S2 C24 104.1(4) . . ?
O5 S2 C24 103.4(4) . . ?
O6 S2 C24 103.3(4) . . ?
F5 C24 F4 110.4(6) . . ?
F5 C24 F6 104.3(7) . . ?
F4 C24 F6 106.6(6) . . ?
F5 C24 S2 113.2(5) . . ?
F4 C24 S2 111.7(6) . . ?
F6 C24 S2 110.2(5) . . ?
O5' S2' O4' 115.7(17) . . ?
O5' S2' O6' 113.6(17) . . ?
O4' S2' O6' 110.1(17) . . ?
O5' S2' C24' 106.0(15) . . ?
O4' S2' C24' 105.5(14) . . ?
O6' S2' C24' 105.0(14) . . ?
F5' C24' F4' 117.9(18) . . ?
F5' C24' F6' 102.5(17) . . ?
F4' C24' F6' 101.8(16) . . ?
F5' C24' S2' 109.9(14) . . ?
F4' C24' S2' 114.5(15) . . ?
F6' C24' S2' 108.9(15) . . ?

_refine_diff_density_max         0.677
_refine_diff_density_min         -0.580
_refine_diff_density_rms         0.097

####################################################################### 
# 
# 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_mk0385
_audit_block_doi                 10.5517/ccdc.csd.cc245ry1
_database_code_depnum_ccdc_archive 'CCDC 1971753'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D0CC07385G 2021
loop_
_audit_author_name
_audit_author_address
'HEMANT RAWAT'
;TATA INSTITUTE OF FUNDAMENTAL RESEARCH HYDERABAD
India
;
_audit_update_record             
;
2020-04-06 deposited with the CCDC.	2021-05-04 downloaded from the CCDC.
;
_audit_creation_date             2020-04-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H32 N2, F6 Sb'
_chemical_formula_sum            'C18 H32 F6 N2 Sb'
_chemical_formula_weight         512.20
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   13.286(3)
_cell_length_b                   16.169(3)
_cell_length_c                   20.044(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.44(3)
_cell_angle_gamma                90
_cell_volume                     4304.7(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    14895
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      59.0
_cell_measurement_theta_min      6.1
_shelx_estimated_absorpt_T_max   0.909
_shelx_estimated_absorpt_T_min   0.867
_exptl_absorpt_coefficient_mu    1.337
_exptl_absorpt_correction_T_max  0.9489
_exptl_absorpt_correction_T_min  0.8132
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'Face indexed'
_exptl_absorpt_special_details   
;
programs X-Red32 and X-Shape by STOE & Cie GmbH 2010
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2072
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.073
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1623
_diffrn_reflns_av_unetI/netI     0.1225
_diffrn_reflns_Laue_measured_fraction_full 0.591
_diffrn_reflns_Laue_measured_fraction_max 0.591
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8280
_diffrn_reflns_point_group_measured_fraction_full 0.591
_diffrn_reflns_point_group_measured_fraction_max 0.591
_diffrn_reflns_theta_full        24.701
_diffrn_reflns_theta_max         24.701
_diffrn_reflns_theta_min         3.238
_diffrn_ambient_temperature      170.15
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.591
_diffrn_measured_fraction_theta_max 0.591
_diffrn_measurement_device_type  'STOE IPDS2T'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1063
_reflns_number_total             2171
_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       'X-Area by STOE & Cie GmbH 2010'
_computing_data_collection       'X-Area by STOE & Cie GmbH 2010'
_computing_data_reduction        'X-Area by STOE & Cie GmbH 2010'
_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         0.534
_refine_diff_density_min         -0.688
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         2171
_refine_ls_number_restraints     77
_refine_ls_R_factor_all          0.1493
_refine_ls_R_factor_gt           0.0555
_refine_ls_restrained_S_all      0.939
_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)+(0.0569P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1356
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C4-C3 \\sim C4A-C3A
 with sigma of 0.02
 N1-C4 \\sim N1-C4A \\sim N2-C3 \\sim N2-C3A
 with sigma of 0.02
3. Rigid bond restraints
 N1, N2, C4, C3, C4A, C3A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
N1 \\sim N2 \\sim C4 \\sim C3 \\sim C4A \\sim C3A: within 1.7A with sigma of
0.04 and sigma for terminal atoms of 0.08
5. Others
 Sof(C4A)=Sof(H4AA)=Sof(H4AB)=Sof(C3A)=Sof(H3AA)=Sof(H3AB)=1-FVAR(1)
 Sof(C4)=Sof(H4A)=Sof(H4B)=Sof(C3)=Sof(H3A)=Sof(H3B)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C6(H6A,H6B), C4(H4A,H4B), C3(H3A,H3B), C4A(H4AA,H4AB),
 C3A(H3AA,H3AB)
6.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C16(H16A,H16B,H16C), C15(H15A,H15B,
 H15C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C10(H10A,H10B,
 H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.8226(12) 0.4228(8) 0.3749(4) 0.057(4) Uani 1 1 d D U . . .
N2 N 0.8305(11) 0.5888(7) 0.3804(3) 0.052(4) Uani 1 1 d D U . . .
C12 C 0.8289(14) 0.6783(10) 0.3791(4) 0.062(5) Uani 1 1 d . . . . .
C17 C 0.8721(17) 0.7116(10) 0.3115(5) 0.085(7) Uani 1 1 d . . . . .
H17A H 0.942583 0.694514 0.308077 0.127 Uiso 1 1 calc GR . . . .
H17B H 0.867933 0.772058 0.310645 0.127 Uiso 1 1 calc GR . . . .
H17C H 0.832668 0.688722 0.273876 0.127 Uiso 1 1 calc GR . . . .
C18 C 0.9024(16) 0.7141(9) 0.4349(5) 0.084(7) Uani 1 1 d . . . . .
H18A H 0.896817 0.681185 0.475651 0.126 Uiso 1 1 calc GR . . . .
H18B H 0.884383 0.771673 0.444167 0.126 Uiso 1 1 calc GR . . . .
H18C H 0.971797 0.711764 0.419476 0.126 Uiso 1 1 calc GR . . . .
C13 C 0.7195(12) 0.6963(11) 0.3907(5) 0.057(5) Uani 1 1 d . . . . .
H13A H 0.696505 0.743171 0.362422 0.069 Uiso 1 1 calc R . . . .
H13B H 0.709737 0.711111 0.437995 0.069 Uiso 1 1 calc R . . . .
C14 C 0.6601(15) 0.6194(9) 0.3730(4) 0.054(5) Uani 1 1 d . . . . .
C16 C 0.5747(13) 0.6136(10) 0.4217(4) 0.059(5) Uani 1 1 d . . . . .
H16A H 0.530379 0.567491 0.408891 0.088 Uiso 1 1 calc GR . . . .
H16B H 0.536219 0.665267 0.420746 0.088 Uiso 1 1 calc GR . . . .
H16C H 0.602470 0.604200 0.466799 0.088 Uiso 1 1 calc GR . . . .
C15 C 0.6162(12) 0.6241(8) 0.3021(4) 0.055(4) Uani 1 1 d . . . . .
H15A H 0.670951 0.624592 0.270317 0.083 Uiso 1 1 calc GR . . . .
H15B H 0.576265 0.674778 0.297003 0.083 Uiso 1 1 calc GR . . . .
H15C H 0.572966 0.575932 0.293542 0.083 Uiso 1 1 calc GR . . . .
C2 C 0.7372(12) 0.5520(9) 0.3779(4) 0.040(3) Uani 1 1 d . . . . .
C1 C 0.7367(12) 0.4644(8) 0.3779(4) 0.038(3) Uani 1 1 d . . . . .
C7 C 0.6486(13) 0.4055(9) 0.3831(4) 0.053(5) Uani 1 1 d . . . . .
C8 C 0.5597(11) 0.4177(9) 0.3354(5) 0.052(4) Uani 1 1 d . . . . .
H8A H 0.583556 0.421498 0.289602 0.079 Uiso 1 1 calc GR . . . .
H8B H 0.524425 0.468893 0.346734 0.079 Uiso 1 1 calc GR . . . .
H8C H 0.513449 0.370793 0.338866 0.079 Uiso 1 1 calc GR . . . .
C9 C 0.6124(12) 0.4022(8) 0.4549(4) 0.054(4) Uani 1 1 d . . . . .
H9A H 0.578888 0.454292 0.465689 0.081 Uiso 1 1 calc GR . . . .
H9B H 0.670158 0.393769 0.485458 0.081 Uiso 1 1 calc GR . . . .
H9C H 0.564828 0.356278 0.459447 0.081 Uiso 1 1 calc GR . . . .
C6 C 0.7011(13) 0.3235(9) 0.3657(5) 0.053(5) Uani 1 1 d . . . . .
H6A H 0.676288 0.278580 0.394625 0.063 Uiso 1 1 calc R . . . .
H6B H 0.685526 0.308540 0.318708 0.063 Uiso 1 1 calc R . . . .
C5 C 0.8115(15) 0.3331(10) 0.3759(5) 0.056(5) Uani 1 1 d . . . . .
C11 C 0.8728(17) 0.2950(9) 0.3195(5) 0.085(7) Uani 1 1 d . . . . .
H11A H 0.854562 0.322071 0.277123 0.128 Uiso 1 1 calc GR . . . .
H11B H 0.858111 0.235717 0.316123 0.128 Uiso 1 1 calc GR . . . .
H11C H 0.944838 0.302894 0.329191 0.128 Uiso 1 1 calc GR . . . .
C10 C 0.8570(16) 0.2998(10) 0.4422(5) 0.079(7) Uani 1 1 d . . . . .
H10A H 0.929110 0.312466 0.444759 0.119 Uiso 1 1 calc GR . . . .
H10B H 0.847397 0.239739 0.444221 0.119 Uiso 1 1 calc GR . . . .
H10C H 0.823380 0.325916 0.479717 0.119 Uiso 1 1 calc GR . . . .
C4 C 0.919(3) 0.4638(18) 0.3539(11) 0.058(6) Uani 0.51(2) 1 d D U P A 1
H4A H 0.916177 0.478253 0.305886 0.070 Uiso 0.51(2) 1 calc R . P A 1
H4B H 0.977901 0.426954 0.362370 0.070 Uiso 0.51(2) 1 calc R . P A 1
C3 C 0.927(3) 0.5416(18) 0.3970(12) 0.061(7) Uani 0.51(2) 1 d D U P A 1
H3A H 0.931439 0.527154 0.445036 0.073 Uiso 0.51(2) 1 calc R . P A 1
H3B H 0.987114 0.574649 0.385674 0.073 Uiso 0.51(2) 1 calc R . P A 1
C4A C 0.920(3) 0.4645(19) 0.3982(12) 0.056(7) Uani 0.49(2) 1 d D U P A 2
H4AA H 0.978084 0.428719 0.388479 0.067 Uiso 0.49(2) 1 calc R . P A 2
H4AB H 0.918902 0.474411 0.446873 0.067 Uiso 0.49(2) 1 calc R . P A 2
C3A C 0.928(2) 0.5467(18) 0.3608(10) 0.051(6) Uani 0.49(2) 1 d D U P A 2
H3AA H 0.987951 0.578566 0.376226 0.061 Uiso 0.49(2) 1 calc R . P A 2
H3AB H 0.930839 0.538177 0.311987 0.061 Uiso 0.49(2) 1 calc R . P A 2
Sb1 Sb 0.77049(9) 0.48552(6) 0.13214(3) 0.0554(4) Uani 1 1 d . . . . .
F1 F 0.8617(12) 0.3965(6) 0.1342(4) 0.110(5) Uani 1 1 d . . . . .
F2 F 0.8348(9) 0.5272(6) 0.0619(3) 0.116(5) Uani 1 1 d . . . . .
F3 F 0.8550(9) 0.5396(7) 0.1899(3) 0.111(5) Uani 1 1 d . . . . .
F4 F 0.6793(10) 0.5735(7) 0.1309(3) 0.105(5) Uani 1 1 d . . . . .
F5 F 0.7116(11) 0.4395(7) 0.2036(3) 0.131(5) Uani 1 1 d . . . . .
F6 F 0.6886(11) 0.4315(7) 0.0741(4) 0.125(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.328(18) . ?
N1 C5 1.457(18) . ?
N1 C4 1.52(3) . ?
N1 C4A 1.52(3) . ?
N2 C12 1.449(18) . ?
N2 C2 1.374(18) . ?
N2 C3 1.52(3) . ?
N2 C3A 1.53(3) . ?
C12 C17 1.579(17) . ?
C12 C18 1.58(2) . ?
C12 C13 1.51(2) . ?
C13 C14 1.51(2) . ?
C14 C16 1.52(2) . ?
C14 C15 1.523(13) . ?
C14 C2 1.50(2) . ?
C2 C1 1.417(18) . ?
C1 C7 1.51(2) . ?
C7 C8 1.514(17) . ?
C7 C9 1.529(13) . ?
C7 C6 1.542(19) . ?
C6 C5 1.48(3) . ?
C5 C11 1.54(2) . ?
C5 C10 1.543(14) . ?
C4 C3 1.53(3) . ?
C4A C3A 1.53(3) . ?
Sb1 F1 1.881(13) . ?
Sb1 F2 1.797(8) . ?
Sb1 F3 1.816(9) . ?
Sb1 F4 1.868(10) . ?
Sb1 F5 1.809(9) . ?
Sb1 F6 1.800(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 114.5(15) . . ?
C1 N1 C4 121.8(17) . . ?
C1 N1 C4A 119.1(18) . . ?
C5 N1 C4 121.7(18) . . ?
C5 N1 C4A 121.5(18) . . ?
C12 N2 C3 121.1(19) . . ?
C12 N2 C3A 117.0(18) . . ?
C2 N2 C12 114.8(14) . . ?
C2 N2 C3 123.1(18) . . ?
C2 N2 C3A 124.7(17) . . ?
N2 C12 C17 110.5(11) . . ?
N2 C12 C18 110.2(11) . . ?
N2 C12 C13 101.8(14) . . ?
C18 C12 C17 104.6(14) . . ?
C13 C12 C17 116.1(12) . . ?
C13 C12 C18 113.8(11) . . ?
C12 C13 C14 107.8(14) . . ?
C13 C14 C16 107.1(10) . . ?
C13 C14 C15 111.3(9) . . ?
C16 C14 C15 109.1(15) . . ?
C2 C14 C13 103.4(14) . . ?
C2 C14 C16 115.7(10) . . ?
C2 C14 C15 110.1(9) . . ?
N2 C2 C14 107.6(13) . . ?
N2 C2 C1 115.9(15) . . ?
C1 C2 C14 136.4(16) . . ?
N1 C1 C2 120.1(15) . . ?
N1 C1 C7 110.6(12) . . ?
C2 C1 C7 129.3(15) . . ?
C1 C7 C9 110.4(9) . . ?
C1 C7 C6 99.8(13) . . ?
C8 C7 C1 117.8(10) . . ?
C8 C7 C9 109.9(13) . . ?
C8 C7 C6 108.7(10) . . ?
C9 C7 C6 109.7(9) . . ?
C5 C6 C7 109.2(13) . . ?
N1 C5 C6 101.7(14) . . ?
N1 C5 C11 109.4(12) . . ?
N1 C5 C10 108.8(11) . . ?
C6 C5 C11 113.3(12) . . ?
C6 C5 C10 116.5(13) . . ?
C11 C5 C10 106.8(15) . . ?
N1 C4 C3 104(2) . . ?
N2 C3 C4 104.1(19) . . ?
N1 C4A C3A 108(2) . . ?
N2 C3A C4A 100.9(19) . . ?
F2 Sb1 F1 89.2(5) . . ?
F2 Sb1 F3 91.1(5) . . ?
F2 Sb1 F4 91.4(5) . . ?
F2 Sb1 F5 176.7(6) . . ?
F2 Sb1 F6 88.1(5) . . ?
F3 Sb1 F1 88.1(5) . . ?
F3 Sb1 F4 91.9(5) . . ?
F4 Sb1 F1 179.4(5) . . ?
F5 Sb1 F1 87.6(5) . . ?
F5 Sb1 F3 88.1(5) . . ?
F5 Sb1 F4 91.8(5) . . ?
F6 Sb1 F1 91.2(6) . . ?
F6 Sb1 F3 179.0(6) . . ?
F6 Sb1 F4 88.8(5) . . ?
F6 Sb1 F5 92.6(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_AJ0678
_audit_block_doi                 10.5517/ccdc.csd.cc245rz2
_database_code_depnum_ccdc_archive 'CCDC 1971754'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D0CC07385G 2021
loop_
_audit_author_name
_audit_author_address
'HEMANT RAWAT'
;TATA INSTITUTE OF FUNDAMENTAL RESEARCH HYDERABAD
India
;
_audit_update_record             
;
2020-05-21 deposited with the CCDC.	2021-05-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H30 N2, 2(C F3 O3 S)'
_chemical_formula_sum            'C20 H30 F6 N2 O6 S2'
_chemical_formula_weight         572.58

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.4927(3)
_cell_length_b                   11.3753(4)
_cell_length_c                   12.8459(4)
_cell_angle_alpha                67.712(3)
_cell_angle_beta                 72.257(3)
_cell_angle_gamma                66.569(3)
_cell_volume                     1280.14(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    10606
_cell_measurement_theta_min      2.9990
_cell_measurement_theta_max      28.8850

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_F_000             596
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.290
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.28806
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25226
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.004
_diffrn_reflns_theta_max         28.875
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.882
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.882
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.882
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5944
_reflns_number_gt                4719
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0550P)²+0.9311P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5944
_refine_ls_number_parameters     394
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1317
_refine_ls_wR_factor_gt          0.1243
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.110
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.7407(2) 0.56981(18) 0.28957(14) 0.0269(4) Uani 1 1 d . . . . .
N2 N 0.76298(17) 0.73267(16) 0.37936(13) 0.0206(3) Uani 1 1 d . . . . .
C1 C 0.7440(2) 0.6903(2) 0.21970(16) 0.0203(4) Uani 1 1 d . . . . .
C2 C 0.75410(19) 0.77955(19) 0.26914(15) 0.0176(4) Uani 1 1 d . . . . .
C3 C 0.7643(2) 0.6065(2) 0.44743(17) 0.0285(5) Uani 1 1 d . . . . .
H3 H 0.777578 0.576538 0.524331 0.034 Uiso 1 1 calc R U . . .
C4 C 0.7464(3) 0.5265(2) 0.40342(18) 0.0357(5) Uani 1 1 d . . . . .
H4 H 0.737758 0.441263 0.450062 0.043 Uiso 1 1 calc R U . . .
C5 C 0.7314(3) 0.4781(2) 0.23380(19) 0.0393(6) Uani 1 1 d . . . . .
C7 C 0.7346(2) 0.7040(2) 0.09907(16) 0.0250(4) Uani 1 1 d . . . . .
C6 C 0.7720(4) 0.5519(3) 0.1085(2) 0.0270(9) Uani 0.706(7) 1 d D . P A 1
H6A H 0.719087 0.543658 0.061046 0.032 Uiso 0.706(7) 1 calc R U P A 1
H6B H 0.874318 0.513281 0.081256 0.032 Uiso 0.706(7) 1 calc R U P A 1
C8 C 0.5866(4) 0.7830(4) 0.0778(3) 0.0313(9) Uani 0.706(7) 1 d D . P A 1
H8A H 0.519988 0.743997 0.139951 0.047 Uiso 0.706(7) 1 calc R U P A 1
H8B H 0.577877 0.780450 0.004954 0.047 Uiso 0.706(7) 1 calc R U P A 1
H8C H 0.565273 0.876254 0.074682 0.047 Uiso 0.706(7) 1 calc R U P A 1
C9 C 0.8456(6) 0.7571(5) 0.0038(4) 0.0307(11) Uani 0.706(7) 1 d D . P A 1
H9A H 0.846014 0.743932 -0.067471 0.046 Uiso 0.706(7) 1 calc R U P A 1
H9B H 0.938985 0.708307 0.025217 0.046 Uiso 0.706(7) 1 calc R U P A 1
H9C H 0.822735 0.852867 -0.007376 0.046 Uiso 0.706(7) 1 calc R U P A 1
C6' C 0.6707(10) 0.5995(9) 0.1129(6) 0.031(2) Uani 0.294(7) 1 d D . P A 2
H6'1 H 0.705991 0.564912 0.045870 0.037 Uiso 0.294(7) 1 calc R U P A 2
H6'2 H 0.566189 0.635093 0.125650 0.037 Uiso 0.294(7) 1 calc R U P A 2
C8' C 0.6234(9) 0.8496(10) 0.0369(7) 0.033(2) Uani 0.294(7) 1 d D . P A 2
H8'1 H 0.661839 0.921914 0.019864 0.050 Uiso 0.294(7) 1 calc R U P A 2
H8'2 H 0.531918 0.866572 0.088514 0.050 Uiso 0.294(7) 1 calc R U P A 2
H8'3 H 0.611013 0.846102 -0.034359 0.050 Uiso 0.294(7) 1 calc R U P A 2
C9' C 0.8752(12) 0.6955(14) 0.0207(10) 0.031(3) Uani 0.294(7) 1 d D . P A 2
H9'1 H 0.944082 0.608019 0.049440 0.046 Uiso 0.294(7) 1 calc R U P A 2
H9'2 H 0.907311 0.766813 0.017745 0.046 Uiso 0.294(7) 1 calc R U P A 2
H9'3 H 0.865963 0.705934 -0.056254 0.046 Uiso 0.294(7) 1 calc R U P A 2
C10 C 0.8508(3) 0.3450(3) 0.2588(3) 0.0509(7) Uani 1 1 d . . . . .
H10A H 0.940345 0.362373 0.242104 0.076 Uiso 1 1 calc R U . . .
H10B H 0.856945 0.292810 0.210766 0.076 Uiso 1 1 calc R U . . .
H10C H 0.831789 0.294353 0.339600 0.076 Uiso 1 1 calc R U . . .
C11 C 0.5871(3) 0.4571(3) 0.2829(2) 0.0408(6) Uani 1 1 d . . . . .
H11A H 0.584017 0.402864 0.363320 0.061 Uiso 1 1 calc R U . . .
H11B H 0.571845 0.410797 0.239479 0.061 Uiso 1 1 calc R U . . .
H11C H 0.513063 0.544344 0.277512 0.061 Uiso 1 1 calc R U . . .
C12 C 0.7678(3) 0.8324(2) 0.42863(19) 0.0334(5) Uani 1 1 d . . . . .
C14 C 0.7593(2) 0.92314(19) 0.21993(17) 0.0225(4) Uani 1 1 d . . . . .
C13 C 0.7238(5) 0.9640(3) 0.3289(3) 0.0269(8) Uani 0.710(6) 1 d D . P B 1
H13A H 0.621393 1.011662 0.346017 0.032 Uiso 0.710(6) 1 calc R U P B 1
H13B H 0.776177 1.024311 0.318883 0.032 Uiso 0.710(6) 1 calc R U P B 1
C15 C 0.6514(4) 1.0210(3) 0.1423(3) 0.0282(9) Uani 0.710(6) 1 d D . P B 1
H15A H 0.681343 1.002480 0.068410 0.042 Uiso 0.710(6) 1 calc R U P B 1
H15B H 0.645570 1.113235 0.130267 0.042 Uiso 0.710(6) 1 calc R U P B 1
H15C H 0.558588 1.009679 0.178560 0.042 Uiso 0.710(6) 1 calc R U P B 1
C16 C 0.9095(4) 0.9227(4) 0.1548(3) 0.0286(8) Uani 0.710(6) 1 d D . P B 1
H16A H 0.977455 0.864698 0.206050 0.043 Uiso 0.710(6) 1 calc R U P B 1
H16B H 0.913912 1.014243 0.127603 0.043 Uiso 0.710(6) 1 calc R U P B 1
H16C H 0.932524 0.889034 0.089284 0.043 Uiso 0.710(6) 1 calc R U P B 1
C13' C 0.8156(12) 0.9326(9) 0.3160(7) 0.032(2) Uani 0.290(6) 1 d D . P B 2
H13C H 0.919873 0.908084 0.298277 0.039 Uiso 0.290(6) 1 calc R U P B 2
H13D H 0.775229 1.024858 0.322659 0.039 Uiso 0.290(6) 1 calc R U P B 2
C15' C 0.6077(8) 1.0251(8) 0.2147(8) 0.032(2) Uani 0.290(6) 1 d D . P B 2
H15D H 0.612422 1.116594 0.184382 0.048 Uiso 0.290(6) 1 calc R U P B 2
H15E H 0.550269 1.012242 0.291688 0.048 Uiso 0.290(6) 1 calc R U P B 2
H15F H 0.564752 1.010540 0.164553 0.048 Uiso 0.290(6) 1 calc R U P B 2
C16' C 0.8563(11) 0.9572(9) 0.1073(8) 0.031(2) Uani 0.290(6) 1 d D . P B 2
H16D H 0.950756 0.891016 0.111192 0.046 Uiso 0.290(6) 1 calc R U P B 2
H16E H 0.861544 1.046672 0.091276 0.046 Uiso 0.290(6) 1 calc R U P B 2
H16F H 0.819553 0.956046 0.046222 0.046 Uiso 0.290(6) 1 calc R U P B 2
C17 C 0.9096(3) 0.7831(4) 0.4635(2) 0.0506(7) Uani 1 1 d . . . . .
H17A H 0.916353 0.849539 0.490981 0.076 Uiso 1 1 calc R U . . .
H17B H 0.984988 0.769864 0.397512 0.076 Uiso 1 1 calc R U . . .
H17C H 0.919613 0.697850 0.524750 0.076 Uiso 1 1 calc R U . . .
C18 C 0.6481(3) 0.8459(2) 0.5296(2) 0.0352(5) Uani 1 1 d . . . . .
H18A H 0.668043 0.763527 0.593453 0.053 Uiso 1 1 calc R U . . .
H18B H 0.559845 0.860940 0.507890 0.053 Uiso 1 1 calc R U . . .
H18C H 0.639003 0.921991 0.552849 0.053 Uiso 1 1 calc R U . . .
S1 S 0.17386(6) 0.52162(5) 0.20811(4) 0.02563(14) Uani 1 1 d . . . . .
O1 O 0.1772(3) 0.4356(2) 0.15092(15) 0.0617(6) Uani 1 1 d . . . . .
O2 O 0.03643(18) 0.6060(2) 0.24364(19) 0.0563(6) Uani 1 1 d . . . . .
O3 O 0.2622(2) 0.4624(2) 0.29194(14) 0.0512(5) Uani 1 1 d . . . . .
F1 F 0.19307(17) 0.70219(16) 0.00692(12) 0.0504(4) Uani 1 1 d . . . . .
F2 F 0.39153(15) 0.57738(16) 0.05789(12) 0.0477(4) Uani 1 1 d . . . . .
F3 F 0.25870(17) 0.73215(16) 0.13435(14) 0.0510(4) Uani 1 1 d . . . . .
C19 C 0.2166(3) 0.9785(2) 0.2991(2) 0.0323(5) Uani 1 1 d . . . . .
S2 S 0.32151(6) 0.83257(5) 0.39559(5) 0.02818(15) Uani 1 1 d . . . . .
O4 O 0.2673(2) 0.72883(16) 0.41103(16) 0.0459(5) Uani 1 1 d . . . . .
O5 O 0.2897(3) 0.8741(2) 0.49569(16) 0.0578(6) Uani 1 1 d . . . . .
O6 O 0.4634(2) 0.8181(2) 0.3371(2) 0.0705(7) Uani 1 1 d . . . . .
F4 F 0.25707(17) 1.08475(13) 0.27137(13) 0.0432(4) Uani 1 1 d . . . . .
F5 F 0.2313(3) 0.95411(17) 0.20243(15) 0.0790(7) Uani 1 1 d . . . . .
F6 F 0.08199(17) 1.01251(18) 0.3448(2) 0.0772(7) Uani 1 1 d . . . . .
C20 C 0.2591(2) 0.6389(2) 0.09723(18) 0.0274(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.331(3) . ?
N1 C4 1.367(3) . ?
N1 C5 1.518(3) . ?
N2 C2 1.329(2) . ?
N2 C3 1.365(3) . ?
N2 C12 1.516(3) . ?
C1 C2 1.436(3) . ?
C1 C7 1.527(3) . ?
C2 C14 1.529(3) . ?
C3 C4 1.332(3) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C5 C6 1.523(4) . ?
C5 C10 1.527(4) . ?
C5 C11 1.529(4) . ?
C5 C6' 1.733(8) . ?
C7 C9' 1.502(11) . ?
C7 C8 1.502(4) . ?
C7 C6' 1.515(8) . ?
C7 C9 1.533(5) . ?
C7 C6 1.579(4) . ?
C7 C8' 1.664(8) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C6' H6'1 0.9900 . ?
C6' H6'2 0.9900 . ?
C8' H8'1 0.9800 . ?
C8' H8'2 0.9800 . ?
C8' H8'3 0.9800 . ?
C9' H9'1 0.9800 . ?
C9' H9'2 0.9800 . ?
C9' H9'3 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C17 1.511(4) . ?
C12 C18 1.512(3) . ?
C12 C13' 1.551(8) . ?
C12 C13 1.566(4) . ?
C14 C16' 1.506(8) . ?
C14 C13 1.533(4) . ?
C14 C15 1.536(4) . ?
C14 C16 1.542(4) . ?
C14 C15' 1.555(8) . ?
C14 C13' 1.575(8) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C13' H13C 0.9900 . ?
C13' H13D 0.9900 . ?
C15' H15D 0.9800 . ?
C15' H15E 0.9800 . ?
C15' H15F 0.9800 . ?
C16' H16D 0.9800 . ?
C16' H16E 0.9800 . ?
C16' H16F 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
S1 O1 1.4140(19) . ?
S1 O3 1.4263(18) . ?
S1 O2 1.4283(19) . ?
S1 C20 1.827(2) . ?
F1 C20 1.343(3) . ?
F2 C20 1.320(2) . ?
F3 C20 1.316(3) . ?
C19 F6 1.312(3) . ?
C19 F5 1.324(3) . ?
C19 F4 1.326(3) . ?
C19 S2 1.823(2) . ?
S2 O6 1.4232(19) . ?
S2 O4 1.4289(18) . ?
S2 O5 1.436(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C4 124.64(18) . . ?
C1 N1 C5 115.08(17) . . ?
C4 N1 C5 120.28(17) . . ?
C2 N2 C3 124.66(17) . . ?
C2 N2 C12 114.88(16) . . ?
C3 N2 C12 120.44(17) . . ?
N1 C1 C2 116.71(17) . . ?
N1 C1 C7 110.22(17) . . ?
C2 C1 C7 133.06(17) . . ?
N2 C2 C1 116.90(17) . . ?
N2 C2 C14 110.20(16) . . ?
C1 C2 C14 132.89(16) . . ?
C4 C3 N2 118.42(19) . . ?
C4 C3 H3 120.8 . . ?
N2 C3 H3 120.8 . . ?
C3 C4 N1 118.42(19) . . ?
C3 C4 H4 120.8 . . ?
N1 C4 H4 120.8 . . ?
N1 C5 C6 99.70(18) . . ?
N1 C5 C10 109.3(2) . . ?
C6 C5 C10 105.9(2) . . ?
N1 C5 C11 107.8(2) . . ?
C6 C5 C11 122.1(3) . . ?
C10 C5 C11 111.1(2) . . ?
N1 C5 C6' 98.1(3) . . ?
C10 C5 C6' 136.3(4) . . ?
C11 C5 C6' 91.1(3) . . ?
C9' C7 C6' 115.8(6) . . ?
C9' C7 C1 111.1(5) . . ?
C8 C7 C1 109.94(19) . . ?
C6' C7 C1 105.8(3) . . ?
C8 C7 C9 112.6(3) . . ?
C1 C7 C9 114.9(3) . . ?
C8 C7 C6 111.3(2) . . ?
C1 C7 C6 100.27(17) . . ?
C9 C7 C6 107.2(3) . . ?
C9' C7 C8' 105.4(6) . . ?
C6' C7 C8' 104.9(5) . . ?
C1 C7 C8' 113.9(3) . . ?
C5 C6 C7 107.5(2) . . ?
C5 C6 H6A 110.2 . . ?
C7 C6 H6A 110.2 . . ?
C5 C6 H6B 110.2 . . ?
C7 C6 H6B 110.2 . . ?
H6A C6 H6B 108.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C6' C5 100.6(4) . . ?
C7 C6' H6'1 111.7 . . ?
C5 C6' H6'1 111.7 . . ?
C7 C6' H6'2 111.7 . . ?
C5 C6' H6'2 111.7 . . ?
H6'1 C6' H6'2 109.4 . . ?
C7 C8' H8'1 109.5 . . ?
C7 C8' H8'2 109.5 . . ?
H8'1 C8' H8'2 109.5 . . ?
C7 C8' H8'3 109.5 . . ?
H8'1 C8' H8'3 109.5 . . ?
H8'2 C8' H8'3 109.5 . . ?
C7 C9' H9'1 109.5 . . ?
C7 C9' H9'2 109.5 . . ?
H9'1 C9' H9'2 109.5 . . ?
C7 C9' H9'3 109.5 . . ?
H9'1 C9' H9'3 109.5 . . ?
H9'2 C9' H9'3 109.5 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C12 C18 111.44(19) . . ?
C17 C12 N2 108.7(2) . . ?
C18 C12 N2 108.87(18) . . ?
C17 C12 C13' 91.6(4) . . ?
C18 C12 C13' 134.4(5) . . ?
N2 C12 C13' 99.3(3) . . ?
C17 C12 C13 121.3(2) . . ?
C18 C12 C13 106.2(2) . . ?
N2 C12 C13 99.33(18) . . ?
C16' C14 C2 117.5(3) . . ?
C2 C14 C13 101.63(17) . . ?
C2 C14 C15 115.01(19) . . ?
C13 C14 C15 109.5(2) . . ?
C2 C14 C16 109.74(19) . . ?
C13 C14 C16 111.1(2) . . ?
C15 C14 C16 109.6(2) . . ?
C16' C14 C15' 110.3(5) . . ?
C2 C14 C15' 110.4(3) . . ?
C16' C14 C13' 108.8(5) . . ?
C2 C14 C13' 101.0(3) . . ?
C15' C14 C13' 108.2(5) . . ?
C14 C13 C12 107.4(2) . . ?
C14 C13 H13A 110.2 . . ?
C12 C13 H13A 110.2 . . ?
C14 C13 H13B 110.2 . . ?
C12 C13 H13B 110.2 . . ?
H13A C13 H13B 108.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C12 C13' C14 106.0(5) . . ?
C12 C13' H13C 110.5 . . ?
C14 C13' H13C 110.5 . . ?
C12 C13' H13D 110.5 . . ?
C14 C13' H13D 110.5 . . ?
H13C C13' H13D 108.7 . . ?
C14 C15' H15D 109.5 . . ?
C14 C15' H15E 109.5 . . ?
H15D C15' H15E 109.5 . . ?
C14 C15' H15F 109.5 . . ?
H15D C15' H15F 109.5 . . ?
H15E C15' H15F 109.5 . . ?
C14 C16' H16D 109.5 . . ?
C14 C16' H16E 109.5 . . ?
H16D C16' H16E 109.5 . . ?
C14 C16' H16F 109.5 . . ?
H16D C16' H16F 109.5 . . ?
H16E C16' H16F 109.5 . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C12 C18 H18A 109.5 . . ?
C12 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C12 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O1 S1 O3 115.80(14) . . ?
O1 S1 O2 115.20(15) . . ?
O3 S1 O2 113.75(13) . . ?
O1 S1 C20 103.77(11) . . ?
O3 S1 C20 102.20(11) . . ?
O2 S1 C20 103.74(11) . . ?
F6 C19 F5 108.7(2) . . ?
F6 C19 F4 107.0(2) . . ?
F5 C19 F4 106.88(19) . . ?
F6 C19 S2 111.90(17) . . ?
F5 C19 S2 110.36(17) . . ?
F4 C19 S2 111.79(15) . . ?
O6 S2 O4 116.87(14) . . ?
O6 S2 O5 112.84(16) . . ?
O4 S2 O5 114.33(12) . . ?
O6 S2 C19 104.11(12) . . ?
O4 S2 C19 103.53(10) . . ?
O5 S2 C19 102.99(12) . . ?
F3 C20 F2 107.73(18) . . ?
F3 C20 F1 106.95(19) . . ?
F2 C20 F1 106.54(18) . . ?
F3 C20 S1 112.16(15) . . ?
F2 C20 S1 111.89(16) . . ?
F1 C20 S1 111.27(14) . . ?

_refine_diff_density_max         1.065
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.063

####################################################################### 
# 
# 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_AJ0776
_audit_block_doi                 10.5517/ccdc.csd.cc245s15
_database_code_depnum_ccdc_archive 'CCDC 1971756'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D0CC07385G 2021
loop_
_audit_author_name
_audit_author_address
'HEMANT RAWAT'
;TATA INSTITUTE OF FUNDAMENTAL RESEARCH HYDERABAD
India
;
_audit_update_record             
;
2020-05-21 deposited with the CCDC.	2021-05-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H38 N2'
_chemical_formula_sum            'C22 H38 N2'
_chemical_formula_weight         330.54

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.3676(6)
_cell_length_b                   20.7476(10)
_cell_length_c                   11.0903(7)
_cell_angle_alpha                90
_cell_angle_beta                 109.300(7)
_cell_angle_gamma                90
_cell_volume                     2034.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8511
_cell_measurement_theta_min      3.4690
_cell_measurement_theta_max      29.0490

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.079
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.062
_shelx_estimated_absorpt_T_min   0.992
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.25625
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32939
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_av_R_equivalents  0.0827
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.504
_diffrn_reflns_theta_max         29.049
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.916
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4978
_reflns_number_gt                3543
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0844P)²+0.2589P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4978
_refine_ls_number_parameters     255
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0583
_refine_ls_wR_factor_ref         0.1649
_refine_ls_wR_factor_gt          0.1533
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.59903(14) 0.65728(6) 0.58768(11) 0.0276(3) Uani 1 1 d . . . . .
C2 C 0.67850(13) 0.60266(6) 0.59610(11) 0.0274(3) Uani 1 1 d . . . . .
C3 C 0.68404(14) 0.58868(6) 0.81609(11) 0.0290(3) Uani 1 1 d . . . . .
H3 H 0.770329 0.619043 0.853258 0.035 Uiso 1 1 calc R U . . .
C4 C 0.53751(15) 0.62711(6) 0.77927(12) 0.0290(3) Uani 1 1 d . . . . .
H4 H 0.451301 0.597005 0.739891 0.035 Uiso 1 1 calc R U . . .
C5 C 0.40303(17) 0.71758(7) 0.63009(15) 0.0420(4) Uani 1 1 d . U . . .
C7 C 0.56634(16) 0.71456(7) 0.49417(13) 0.0368(3) Uani 1 1 d . . . . .
C8 C 0.6904(2) 0.76514(8) 0.54381(18) 0.0581(5) Uani 1 1 d . . . . .
H8A H 0.709323 0.772334 0.635111 0.087 Uiso 1 1 calc R U . . .
H8B H 0.658139 0.805613 0.497203 0.087 Uiso 1 1 calc R U . . .
H8C H 0.783379 0.749926 0.530966 0.087 Uiso 1 1 calc R U . . .
C9 C 0.5373(2) 0.70332(9) 0.35246(15) 0.0522(4) Uani 1 1 d . . . . .
H9A H 0.631471 0.689821 0.339485 0.078 Uiso 1 1 calc R U . . .
H9B H 0.501115 0.743323 0.305305 0.078 Uiso 1 1 calc R U . . .
H9C H 0.460787 0.669558 0.321342 0.078 Uiso 1 1 calc R U . . .
C6 C 0.4116(4) 0.73682(17) 0.5012(3) 0.0481(7) Uani 0.847(4) 1 d . . P A 1
H6A H 0.401649 0.784152 0.490535 0.058 Uiso 0.847(4) 1 calc R U P A 1
H6B H 0.328504 0.716257 0.432246 0.058 Uiso 0.847(4) 1 calc R U P A 1
C10 C 0.4171(3) 0.77894(10) 0.7147(2) 0.0592(7) Uani 0.847(4) 1 d . U P A 1
H10A H 0.414545 0.766352 0.799155 0.089 Uiso 0.847(4) 1 calc R U P A 1
H10B H 0.332789 0.808187 0.674109 0.089 Uiso 0.847(4) 1 calc R U P A 1
H10C H 0.512963 0.800784 0.724075 0.089 Uiso 0.847(4) 1 calc R U P A 1
C11 C 0.2538(2) 0.68424(11) 0.6141(2) 0.0553(7) Uani 0.847(4) 1 d . U P A 1
H11A H 0.245261 0.675712 0.698417 0.083 Uiso 0.847(4) 1 calc R U P A 1
H11B H 0.249444 0.643433 0.568570 0.083 Uiso 0.847(4) 1 calc R U P A 1
H11C H 0.170121 0.712041 0.565123 0.083 Uiso 0.847(4) 1 calc R U P A 1
C6' C 0.459(2) 0.7583(8) 0.5338(17) 0.046(4) Uani 0.153(4) 1 d . . P A 2
H6'1 H 0.372228 0.771012 0.458336 0.055 Uiso 0.153(4) 1 calc R U P A 2
H6'2 H 0.511979 0.797724 0.575702 0.055 Uiso 0.153(4) 1 calc R U P A 2
C10' C 0.307(2) 0.7470(8) 0.6915(14) 0.078(5) Uani 0.153(4) 1 d . U P A 2
H10D H 0.255035 0.713376 0.723380 0.117 Uiso 0.153(4) 1 calc R U P A 2
H10E H 0.231784 0.774133 0.629943 0.117 Uiso 0.153(4) 1 calc R U P A 2
H10F H 0.367945 0.773506 0.763028 0.117 Uiso 0.153(4) 1 calc R U P A 2
C11' C 0.2765(12) 0.6620(6) 0.5329(12) 0.056(3) Uani 0.153(4) 1 d . U P A 2
H11D H 0.322860 0.641383 0.475442 0.083 Uiso 0.153(4) 1 calc R U P A 2
H11E H 0.183830 0.684306 0.482350 0.083 Uiso 0.153(4) 1 calc R U P A 2
H11F H 0.251866 0.629139 0.586369 0.083 Uiso 0.153(4) 1 calc R U P A 2
C12 C 0.84244(18) 0.52072(8) 0.71786(15) 0.0466(4) Uani 1 1 d . . . . .
C13 C 0.8302(2) 0.51319(9) 0.57857(17) 0.0583(5) Uani 1 1 d . . . . .
H13A H 0.769252 0.474566 0.541871 0.070 Uiso 1 1 calc R U . . .
H13B H 0.932158 0.507666 0.571602 0.070 Uiso 1 1 calc R U . . .
C14 C 0.75454(16) 0.57368(7) 0.50509(13) 0.0381(3) Uani 1 1 d . . . . .
C15 C 0.8747(2) 0.61759(9) 0.4832(2) 0.0612(5) Uani 1 1 d . . . . .
H15A H 0.826674 0.657046 0.439873 0.092 Uiso 1 1 calc R U . . .
H15B H 0.924292 0.595184 0.430071 0.092 Uiso 1 1 calc R U . . .
H15C H 0.950045 0.628684 0.565609 0.092 Uiso 1 1 calc R U . . .
C16 C 0.6438(2) 0.55032(9) 0.37783(16) 0.0615(5) Uani 1 1 d . . . . .
H16A H 0.560282 0.527114 0.393092 0.092 Uiso 1 1 calc R U . . .
H16B H 0.696364 0.521423 0.336528 0.092 Uiso 1 1 calc R U . . .
H16C H 0.603822 0.587425 0.322257 0.092 Uiso 1 1 calc R U . . .
C17 C 0.8385(3) 0.45200(9) 0.7698(2) 0.0753(7) Uani 1 1 d . . . . .
H17A H 0.868586 0.453393 0.863183 0.113 Uiso 1 1 calc R U . . .
H17B H 0.908542 0.424346 0.744511 0.113 Uiso 1 1 calc R U . . .
H17C H 0.735714 0.434620 0.734607 0.113 Uiso 1 1 calc R U . . .
C18 C 0.9845(2) 0.55624(11) 0.7966(2) 0.0726(6) Uani 1 1 d . . . . .
H18A H 0.981882 0.600418 0.764662 0.109 Uiso 1 1 calc R U . . .
H18B H 1.073693 0.533944 0.789618 0.109 Uiso 1 1 calc R U . . .
H18C H 0.989621 0.557262 0.886263 0.109 Uiso 1 1 calc R U . . .
C19 C 0.68597(18) 0.53850(7) 0.91730(13) 0.0402(4) Uani 1 1 d . . . . .
H19A H 0.605898 0.506203 0.879339 0.048 Uiso 1 1 calc R U . . .
H19B H 0.784486 0.515821 0.943794 0.048 Uiso 1 1 calc R U . . .
C20 C 0.6613(2) 0.56773(8) 1.03476(14) 0.0501(4) Uani 1 1 d . . . . .
H20A H 0.654850 0.532760 1.093482 0.060 Uiso 1 1 calc R U . . .
H20B H 0.748926 0.595241 1.080201 0.060 Uiso 1 1 calc R U . . .
C21 C 0.5197(2) 0.60725(8) 0.99969(15) 0.0529(4) Uani 1 1 d . . . . .
H21A H 0.513223 0.629452 1.076733 0.063 Uiso 1 1 calc R U . . .
H21B H 0.430721 0.578573 0.967201 0.063 Uiso 1 1 calc R U . . .
C22 C 0.51705(19) 0.65689(7) 0.89837(14) 0.0422(4) Uani 1 1 d . . . . .
H22A H 0.598679 0.688686 0.935158 0.051 Uiso 1 1 calc R U . . .
H22B H 0.419429 0.680227 0.873505 0.051 Uiso 1 1 calc R U . . .
N1 N 0.53804(12) 0.67616(5) 0.68516(10) 0.0307(3) Uani 1 1 d . . . . .
N2 N 0.70190(12) 0.55879(5) 0.70229(10) 0.0313(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3420(18) . ?
C1 N1 1.4342(16) . ?
C1 C7 1.5402(18) . ?
C2 N2 1.4467(16) . ?
C2 C14 1.5372(17) . ?
C3 N2 1.4646(15) . ?
C3 C4 1.5219(18) . ?
C3 C19 1.5267(18) . ?
C3 H3 1.0000 . ?
C4 N1 1.4590(16) . ?
C4 C22 1.5266(17) . ?
C4 H4 1.0000 . ?
C5 C10' 1.432(12) . ?
C5 N1 1.4834(17) . ?
C5 C6 1.511(4) . ?
C5 C11 1.517(3) . ?
C5 C10 1.561(3) . ?
C5 C6' 1.581(18) . ?
C5 C11' 1.747(14) . ?
C7 C9 1.522(2) . ?
C7 C6' 1.52(2) . ?
C7 C8 1.527(2) . ?
C7 C6 1.547(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C6' H6'1 0.9900 . ?
C6' H6'2 0.9900 . ?
C10' H10D 0.9800 . ?
C10' H10E 0.9800 . ?
C10' H10F 0.9800 . ?
C11' H11D 0.9800 . ?
C11' H11E 0.9800 . ?
C11' H11F 0.9800 . ?
C12 N2 1.4956(17) . ?
C12 C13 1.519(2) . ?
C12 C18 1.519(3) . ?
C12 C17 1.543(2) . ?
C13 C14 1.536(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C16 1.528(2) . ?
C14 C15 1.528(2) . ?
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 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.522(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.497(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.518(2) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9900 . ?
C22 H22B 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 C1 N1 121.89(11) . . ?
C2 C1 C7 132.90(11) . . ?
N1 C1 C7 104.87(10) . . ?
C1 C2 N2 121.28(11) . . ?
C1 C2 C14 130.65(11) . . ?
N2 C2 C14 108.06(10) . . ?
N2 C3 C4 109.90(10) . . ?
N2 C3 C19 111.58(10) . . ?
C4 C3 C19 110.18(11) . . ?
N2 C3 H3 108.4 . . ?
C4 C3 H3 108.4 . . ?
C19 C3 H3 108.4 . . ?
N1 C4 C3 109.96(10) . . ?
N1 C4 C22 111.58(10) . . ?
C3 C4 C22 109.87(11) . . ?
N1 C4 H4 108.4 . . ?
C3 C4 H4 108.4 . . ?
C22 C4 H4 108.4 . . ?
C10' C5 N1 129.5(5) . . ?
N1 C5 C6 103.74(16) . . ?
N1 C5 C11 114.29(12) . . ?
C6 C5 C11 110.20(18) . . ?
N1 C5 C10 109.49(14) . . ?
C6 C5 C10 109.45(18) . . ?
C11 C5 C10 109.49(16) . . ?
C10' C5 C6' 119.6(9) . . ?
N1 C5 C6' 99.2(7) . . ?
C10' C5 C11' 99.7(9) . . ?
N1 C5 C11' 100.6(4) . . ?
C6' C5 C11' 104.1(7) . . ?
C9 C7 C6' 118.7(7) . . ?
C9 C7 C8 109.42(13) . . ?
C6' C7 C8 89.0(7) . . ?
C9 C7 C1 120.33(13) . . ?
C6' C7 C1 105.6(6) . . ?
C8 C7 C1 109.22(12) . . ?
C9 C7 C6 104.34(17) . . ?
C8 C7 C6 112.99(18) . . ?
C1 C7 C6 100.21(16) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 C6 C7 108.2(2) . . ?
C5 C6 H6A 110.1 . . ?
C7 C6 H6A 110.1 . . ?
C5 C6 H6B 110.1 . . ?
C7 C6 H6B 110.1 . . ?
H6A C6 H6B 108.4 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C7 C6' C5 105.9(9) . . ?
C7 C6' H6'1 110.5 . . ?
C5 C6' H6'1 110.5 . . ?
C7 C6' H6'2 110.5 . . ?
C5 C6' H6'2 110.5 . . ?
H6'1 C6' H6'2 108.7 . . ?
C5 C10' H10D 109.5 . . ?
C5 C10' H10E 109.5 . . ?
H10D C10' H10E 109.5 . . ?
C5 C10' H10F 109.5 . . ?
H10D C10' H10F 109.5 . . ?
H10E C10' H10F 109.5 . . ?
C5 C11' H11D 109.5 . . ?
C5 C11' H11E 109.5 . . ?
H11D C11' H11E 109.5 . . ?
C5 C11' H11F 109.5 . . ?
H11D C11' H11F 109.5 . . ?
H11E C11' H11F 109.5 . . ?
N2 C12 C13 99.75(11) . . ?
N2 C12 C18 112.37(14) . . ?
C13 C12 C18 113.06(15) . . ?
N2 C12 C17 113.72(14) . . ?
C13 C12 C17 106.35(15) . . ?
C18 C12 C17 111.00(16) . . ?
C12 C13 C14 108.78(12) . . ?
C12 C13 H13A 109.9 . . ?
C14 C13 H13A 109.9 . . ?
C12 C13 H13B 109.9 . . ?
C14 C13 H13B 109.9 . . ?
H13A C13 H13B 108.3 . . ?
C16 C14 C15 110.67(14) . . ?
C16 C14 C13 106.50(14) . . ?
C15 C14 C13 109.66(13) . . ?
C16 C14 C2 114.21(13) . . ?
C15 C14 C2 113.36(13) . . ?
C13 C14 C2 101.76(11) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C12 C18 H18A 109.5 . . ?
C12 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C12 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C3 112.91(12) . . ?
C20 C19 H19A 109.0 . . ?
C3 C19 H19A 109.0 . . ?
C20 C19 H19B 109.0 . . ?
C3 C19 H19B 109.0 . . ?
H19A C19 H19B 107.8 . . ?
C21 C20 C19 111.59(12) . . ?
C21 C20 H20A 109.3 . . ?
C19 C20 H20A 109.3 . . ?
C21 C20 H20B 109.3 . . ?
C19 C20 H20B 109.3 . . ?
H20A C20 H20B 108.0 . . ?
C20 C21 C22 111.10(13) . . ?
C20 C21 H21A 109.4 . . ?
C22 C21 H21A 109.4 . . ?
C20 C21 H21B 109.4 . . ?
C22 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
C21 C22 C4 112.94(12) . . ?
C21 C22 H22A 109.0 . . ?
C4 C22 H22A 109.0 . . ?
C21 C22 H22B 109.0 . . ?
C4 C22 H22B 109.0 . . ?
H22A C22 H22B 107.8 . . ?
C1 N1 C4 116.43(10) . . ?
C1 N1 C5 110.23(10) . . ?
C4 N1 C5 119.64(10) . . ?
C2 N2 C3 113.91(10) . . ?
C2 N2 C12 108.48(10) . . ?
C3 N2 C12 118.10(11) . . ?

_refine_diff_density_max         0.232
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.043

