# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_r232
_database_code_depnum_ccdc_archive 'CCDC 2075639'
loop_
_audit_author_name
_audit_author_address
'Farzaneh Fadaei Tirani'
;EPFL ISIC
Switzerland
;
_audit_update_record             
;
2021-04-06 deposited with the CCDC.	2021-06-04 downloaded from the CCDC.
;
_audit_creation_date             2020-11-02
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H25 N3 O2'
_chemical_formula_sum            'C23 H25 N3 O2'
_chemical_formula_weight         375.46
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C23 H25 N3 O2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   11.4016(3)
_cell_length_b                   9.5092(2)
_cell_length_c                   19.0932(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.950(2)
_cell_angle_gamma                90
_cell_volume                     2054.86(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5393
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      76.4150
_cell_measurement_theta_min      3.8580
_shelx_estimated_absorpt_T_max   0.857
_shelx_estimated_absorpt_T_min   0.787
_exptl_absorpt_coefficient_mu    0.625
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.530
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear intense yellow'
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             800
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.1266
1 0 -1 0.1442
-1 0 1 0.1583
-1 -2 -2 0.1822
-1 -1 -1 0.1747
1 1 1 0.1763
2 1 -1 0.1750
0 0 -1 0.0948
0 1 -2 0.1456
0 -1 2 0.2291
-1 2 -2 0.1736
1 -2 2 0.2170
-2 0 -1 0.1196
4 -4 5 0.1919
3 -6 0 0.2006
0 6 1 0.1641
3 -6 -3 0.1887
-3 6 3 0.1612
-4 4 8 0.1401
4 -4 -8 0.1631
-6 -3 1 0.1714
0 5 7 0.1642
-3 0 12 0.1461
-3 -4 -7 0.1510
2 3 10 0.1732
5 4 2 0.1692
-4 -4 8 0.2109
1 0 12 0.1574
3 -3 8 0.1821
6 0 7 0.1426
4 -5 1 0.1806

_exptl_crystal_size_max          0.403
_exptl_crystal_size_mid          0.285
_exptl_crystal_size_min          0.254
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0000 -0.0000 0.0000 0.0418 -0.0784 0.1031
1.0000 -0.0000 -1.0000 0.1130 -0.0416 0.0892
-1.0000 0.0000 1.0000 -0.1130 0.0416 -0.0892
-1.0000 -2.0000 -2.0000 0.1802 -0.0817 -0.3408
-1.0000 -1.0000 -1.0000 0.0692 -0.0017 -0.2220
1.0000 1.0000 1.0000 -0.0692 0.0017 0.2220
2.0000 1.0000 -1.0000 0.1150 -0.0032 0.2973
-0.0000 -0.0000 -1.0000 0.0712 0.0367 -0.0139
-0.0000 1.0000 -2.0000 0.1027 0.1902 0.0772
0.0000 -1.0000 2.0000 -0.1027 -0.1902 -0.0772
-1.0000 2.0000 -2.0000 0.0212 0.3854 0.0791
1.0000 -2.0000 2.0000 -0.0212 -0.3854 -0.0791
-2.0000 0.0000 -1.0000 -0.0123 0.1934 -0.2201
3.9932 -4.2757 5.0888 -0.0257 -0.9991 0.0336
3.0000 -6.0000 0.0000 0.3638 -0.9357 -0.3204
0.0000 6.0000 1.0000 -0.3097 0.6639 0.6436
3.0000 -6.0000 -3.0000 0.5774 -0.8256 -0.3620
-3.0000 6.0000 3.0000 -0.5774 0.8256 0.3620
-4.0000 4.0000 8.0000 -0.8958 0.4867 0.1183
4.0000 -4.0000 -8.0000 0.8958 -0.4867 -0.1183
-6.0000 -3.0000 1.0000 -0.2025 0.0831 -0.9197
0.0000 5.0000 7.0000 -0.6973 0.3268 0.6219
-3.0000 0.0000 12.0000 -0.9799 -0.2057 -0.1429
-3.0000 -4.0000 -7.0000 0.5323 0.0251 -0.8263
2.0000 3.0000 10.0000 -0.7479 -0.1737 0.6599
5.0000 4.0000 2.0000 -0.0927 0.0019 0.9632
-4.0000 -4.0000 8.0000 -0.5777 -0.4475 -0.7213
1.0000 0.0000 12.0000 -0.8128 -0.5191 0.2696
3.0000 -3.0000 8.0000 -0.3252 -0.8792 0.1055
6.0000 -0.0000 7.0000 -0.2480 -0.7273 0.7159
4.0000 -5.0000 1.0000 0.2946 -0.9340 -0.0984

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11847
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.556
_diffrn_reflns_theta_min         3.906
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2665
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -13.00   1.00    1.00    --  -43.01 -66.00-138.00  103
  2  ω    -62.00  23.00   1.00    1.00    --  -43.01  66.00  -3.00   85
  3  ω     93.00 177.00   1.00    4.00    --  112.00  66.00  -3.00   84
  4  ω     39.00 102.00   1.00    4.00    --  112.00 -66.00-138.00   63
  5  ω     47.00  84.00   1.00    1.00    --   43.01-125.00 150.00   37
  6  ω     21.00  77.00   1.00    1.00    --   43.01 -99.00  60.00   56
  7  ω    104.00 145.00   1.00    4.00    --  112.00  77.00 -60.00   41
  8  ω    144.00 176.00   1.00    4.00    --  112.00  77.00-120.00   32
  9  ω    109.00 135.00   1.00    4.00    --  112.00  30.00 -30.00   26
 10  ω    146.00 175.00   1.00    4.00    --  112.00  30.00 -30.00   29
 11  ω    125.00 160.00   1.00    4.00    --  112.00 111.00-150.00   35
 12  ω     40.00 109.00   1.00    4.00    --  112.00-111.00-120.00   69
 13  ω     39.00 108.00   1.00    4.00    --  112.00-111.00-150.00   69
 14  ω     41.00 127.00   1.00    4.00    --  112.00 -61.00 -90.00   86
 15  ω    123.00 175.00   1.00    4.00    --  112.00 111.00-180.00   52
 16  ω    131.00 156.00   1.00    4.00    --  112.00  77.00-180.00   25
 17  ω    104.00 176.00   1.00    4.00    --  112.00  77.00 -90.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0417568000
_diffrn_orient_matrix_UB_12      -0.0397535000
_diffrn_orient_matrix_UB_13      -0.0712166000
_diffrn_orient_matrix_UB_21      -0.0783598000
_diffrn_orient_matrix_UB_22      0.1167764000
_diffrn_orient_matrix_UB_23      -0.0367277000
_diffrn_orient_matrix_UB_31      0.1031231000
_diffrn_orient_matrix_UB_32      0.1049614000
_diffrn_orient_matrix_UB_33      0.0138737000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3775
_reflns_number_total             4260
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         4260
_refine_ls_number_restraints     67
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0452
_refine_ls_restrained_S_all      1.037
_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)+(0.0880P)²+0.2554P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1244
_refine_ls_wR_factor_ref         0.1321
_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
 C25-C21 \\sim C24-C21 \\sim C21-C22 \\sim C23-C21
 with sigma of 0.02
 C25-C23 \\sim C24-C22
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C21 \\sim C22 \\sim C23 \\sim C24 \\sim C25: within 2A with sigma of 0.02 and
sigma for terminal atoms of 0.04 within 2A
4. Rigid body (RIGU) restrains
 C22, C21, C23, C24, C25
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(H21A)=Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(H22C)=Sof(C24)=Sof(H24A)=Sof(H24B)=
 Sof(H24C)=1-FVAR(1)
 Sof(H21)=Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(H23C)=Sof(C25)=Sof(H25A)=Sof(H25B)=
 Sof(H25C)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C21(H21A), C21(H21)
6.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,
 H25C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.31370(7) 0.12980(9) 0.51193(4) 0.0321(2) Uani 1 1 d . . . . .
O2 O 0.30409(8) 0.05107(10) 0.40258(5) 0.0419(2) Uani 1 1 d . . . . .
N1 N 0.31035(8) 0.20895(10) 0.62715(5) 0.0307(2) Uani 1 1 d . . . . .
N2 N 0.20422(8) 0.16064(10) 0.61568(5) 0.0305(2) Uani 1 1 d . . . . .
N3 N 0.14421(9) 0.16765(11) 0.67007(5) 0.0327(2) Uani 1 1 d . . . . .
C1 C 0.37060(10) 0.19789(11) 0.56882(5) 0.0290(2) Uani 1 1 d . . . . .
C2 C 0.36351(10) 0.11346(12) 0.44956(6) 0.0329(2) Uani 1 1 d . . . . .
C3 C 0.47666(11) 0.17673(12) 0.44773(6) 0.0340(3) Uani 1 1 d . . . . .
H3 H 0.5066(15) 0.1735(18) 0.4030(10) 0.046(4) Uiso 1 1 d . . . . .
C4 C 0.53476(10) 0.24583(11) 0.50477(6) 0.0299(2) Uani 1 1 d . . . . .
C5 C 0.48101(10) 0.25435(11) 0.56919(6) 0.0288(2) Uani 1 1 d . . . . .
C6 C 0.64706(10) 0.31895(12) 0.49526(6) 0.0311(2) Uani 1 1 d . . . . .
C7 C 0.72562(11) 0.25804(14) 0.45321(7) 0.0382(3) Uani 1 1 d . . . . .
H7 H 0.7152(15) 0.1595(19) 0.4381(9) 0.045(4) Uiso 1 1 d . . . . .
C8 C 0.82317(12) 0.33283(16) 0.43652(7) 0.0441(3) Uani 1 1 d . . . . .
H8 H 0.8765(16) 0.288(2) 0.4083(10) 0.054(5) Uiso 1 1 d . . . . .
C9 C 0.84514(11) 0.46721(15) 0.46240(7) 0.0415(3) Uani 1 1 d . . . . .
H9 H 0.9114(15) 0.5239(18) 0.4517(9) 0.045(4) Uiso 1 1 d . . . . .
C10 C 0.76978(11) 0.52695(13) 0.50587(7) 0.0382(3) Uani 1 1 d . . . . .
H10 H 0.7847(14) 0.6186(18) 0.5246(9) 0.043(4) Uiso 1 1 d . . . . .
C11 C 0.67121(10) 0.45348(12) 0.52219(6) 0.0344(3) Uani 1 1 d . . . . .
H11 H 0.6137(15) 0.499(2) 0.5518(10) 0.051(4) Uiso 1 1 d . . . . .
C12 C 0.54013(10) 0.31472(12) 0.63672(6) 0.0299(2) Uani 1 1 d . . . . .
C13 C 0.49368(11) 0.43219(13) 0.66755(7) 0.0378(3) Uani 1 1 d . . . . .
H13 H 0.4254(15) 0.4791(19) 0.6440(9) 0.049(4) Uiso 1 1 d . . . . .
C14 C 0.54598(13) 0.48100(15) 0.73283(7) 0.0447(3) Uani 1 1 d . . . . .
H14 H 0.5123(16) 0.563(2) 0.7537(11) 0.057(5) Uiso 1 1 d . . . . .
C15 C 0.64354(13) 0.41300(15) 0.76720(7) 0.0451(3) Uani 1 1 d . . . . .
H15 H 0.6800(16) 0.448(2) 0.8147(10) 0.055(5) Uiso 1 1 d . . . . .
C16 C 0.69069(13) 0.29727(15) 0.73656(7) 0.0446(3) Uani 1 1 d . . . . .
H16 H 0.7612(18) 0.247(2) 0.7623(11) 0.059(5) Uiso 1 1 d . . . . .
C17 C 0.63912(11) 0.24848(12) 0.67110(6) 0.0361(3) Uani 1 1 d . . . . .
H17 H 0.6706(13) 0.1657(17) 0.6505(8) 0.036(4) Uiso 1 1 d . . . . .
C18 C 0.19257(12) 0.23587(13) 0.73707(6) 0.0363(3) Uani 1 1 d . . . . .
H18 H 0.2773(14) 0.2194(15) 0.7408(8) 0.033(3) Uiso 1 1 d . . . . .
C19 C 0.17016(16) 0.39402(15) 0.73302(8) 0.0493(3) Uani 1 1 d . . . . .
H19A H 0.0842(17) 0.412(2) 0.7295(10) 0.056(5) Uiso 1 1 d . . . . .
H19B H 0.2074(17) 0.437(2) 0.7762(11) 0.062(5) Uiso 1 1 d . . . . .
H19C H 0.2032(16) 0.433(2) 0.6923(11) 0.056(5) Uiso 1 1 d . . . . .
C20 C 0.14689(16) 0.16670(17) 0.80029(7) 0.0488(3) Uani 1 1 d . . . . .
H20A H 0.1593(17) 0.065(2) 0.7987(10) 0.061(5) Uiso 1 1 d . . . . .
H20B H 0.0609(19) 0.188(2) 0.8034(11) 0.062(5) Uiso 1 1 d . . . . .
H20C H 0.1885(17) 0.205(2) 0.8432(11) 0.058(5) Uiso 1 1 d . . . . .
C21 C 0.01955(11) 0.12387(14) 0.65331(7) 0.0386(3) Uani 1 1 d D U . . .
H21A H -0.002724 0.068440 0.694200 0.046 Uiso 0.092(6) 1 calc R U P A 2
H21 H -0.017451 0.124456 0.698192 0.046 Uiso 0.908(6) 1 calc R U P A 1
C22 C -0.0612(14) 0.2519(16) 0.6437(16) 0.060(5) Uani 0.092(6) 1 d D U P A 2
H22A H -0.064208 0.297651 0.689492 0.091 Uiso 0.092(6) 1 calc R U P A 2
H22B H -0.140885 0.222154 0.624406 0.091 Uiso 0.092(6) 1 calc R U P A 2
H22C H -0.030486 0.318308 0.611183 0.091 Uiso 0.092(6) 1 calc R U P A 2
C23 C -0.04826(15) 0.2265(3) 0.60266(15) 0.0591(7) Uani 0.908(6) 1 d D U P A 1
H23A H -0.046213 0.320226 0.624154 0.089 Uiso 0.908(6) 1 calc R U P A 1
H23B H -0.130439 0.195272 0.592381 0.089 Uiso 0.908(6) 1 calc R U P A 1
H23C H -0.011884 0.230380 0.558746 0.089 Uiso 0.908(6) 1 calc R U P A 1
C24 C 0.0010(17) 0.030(3) 0.5876(13) 0.067(6) Uani 0.092(6) 1 d D U P A 2
H24A H 0.010850 0.085805 0.545667 0.100 Uiso 0.092(6) 1 calc R U P A 2
H24B H -0.078882 -0.009949 0.583022 0.100 Uiso 0.092(6) 1 calc R U P A 2
H24C H 0.059125 -0.046570 0.592281 0.100 Uiso 0.092(6) 1 calc R U P A 2
C25 C 0.01335(16) -0.0251(2) 0.62474(12) 0.0505(5) Uani 0.908(6) 1 d D U P A 1
H25A H 0.047039 -0.027926 0.579912 0.076 Uiso 0.908(6) 1 calc R U P A 1
H25B H -0.069275 -0.055761 0.617108 0.076 Uiso 0.908(6) 1 calc R U P A 1
H25C H 0.058284 -0.087946 0.658746 0.076 Uiso 0.908(6) 1 calc R U P A 1


_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
O1 C1 1.3599(13) . ?
O1 C2 1.3888(13) . ?
O2 C2 1.2118(15) . ?
N1 N2 1.2880(14) . ?
N1 C1 1.3814(14) . ?
N2 N3 1.3127(13) . ?
N3 C18 1.4801(15) . ?
N3 C21 1.4784(15) . ?
C1 C5 1.3678(16) . ?
C2 C3 1.4277(17) . ?
C3 C4 1.3719(16) . ?
C4 C5 1.4413(15) . ?
C4 C6 1.4873(16) . ?
C5 C12 1.4953(14) . ?
C6 C7 1.3987(16) . ?
C6 C11 1.3937(17) . ?
C7 C8 1.3894(18) . ?
C8 C9 1.382(2) . ?
C9 C10 1.3865(19) . ?
C10 C11 1.3903(17) . ?
C12 C13 1.3965(16) . ?
C12 C17 1.3864(17) . ?
C13 C14 1.3945(18) . ?
C14 C15 1.382(2) . ?
C15 C16 1.385(2) . ?
C16 C17 1.3947(17) . ?
C18 C19 1.5258(18) . ?
C18 C20 1.5209(17) . ?
C21 C22 1.524(12) . ?
C21 C23 1.518(2) . ?
C21 C24 1.534(13) . ?
C21 C25 1.517(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 O1 C2 122.22(9) . . ?
N2 N1 C1 112.60(9) . . ?
N1 N2 N3 114.60(9) . . ?
N2 N3 C18 122.06(10) . . ?
N2 N3 C21 113.20(9) . . ?
C21 N3 C18 123.94(9) . . ?
O1 C1 N1 116.39(9) . . ?
O1 C1 C5 122.74(10) . . ?
C5 C1 N1 120.88(10) . . ?
O1 C2 C3 115.99(9) . . ?
O2 C2 O1 116.08(10) . . ?
O2 C2 C3 127.89(11) . . ?
C4 C3 C2 122.23(10) . . ?
C3 C4 C5 119.34(10) . . ?
C3 C4 C6 117.85(10) . . ?
C5 C4 C6 122.62(10) . . ?
C1 C5 C4 117.36(10) . . ?
C1 C5 C12 118.27(10) . . ?
C4 C5 C12 124.30(10) . . ?
C7 C6 C4 119.80(10) . . ?
C11 C6 C4 121.24(10) . . ?
C11 C6 C7 118.70(11) . . ?
C8 C7 C6 120.38(12) . . ?
C9 C8 C7 120.44(12) . . ?
C8 C9 C10 119.62(12) . . ?
C9 C10 C11 120.30(12) . . ?
C10 C11 C6 120.50(11) . . ?
C13 C12 C5 121.07(10) . . ?
C17 C12 C5 119.35(10) . . ?
C17 C12 C13 119.49(11) . . ?
C14 C13 C12 120.00(12) . . ?
C15 C14 C13 120.09(12) . . ?
C14 C15 C16 120.16(12) . . ?
C15 C16 C17 119.98(13) . . ?
C12 C17 C16 120.27(12) . . ?
N3 C18 C19 110.22(10) . . ?
N3 C18 C20 111.65(11) . . ?
C20 C18 C19 113.28(11) . . ?
N3 C21 C22 110.6(7) . . ?
N3 C21 C23 111.04(11) . . ?
N3 C21 C24 112.0(7) . . ?
N3 C21 C25 110.04(11) . . ?
C22 C21 C24 110.3(11) . . ?
C25 C21 C23 111.94(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C5 C4 3.10(16) . . . . ?
O1 C1 C5 C12 -174.21(9) . . . . ?
O1 C2 C3 C4 1.99(17) . . . . ?
O2 C2 C3 C4 179.46(12) . . . . ?
N1 N2 N3 C18 4.49(15) . . . . ?
N1 N2 N3 C21 174.59(9) . . . . ?
N1 C1 C5 C4 -176.26(9) . . . . ?
N1 C1 C5 C12 6.44(15) . . . . ?
N2 N1 C1 O1 -4.89(14) . . . . ?
N2 N1 C1 C5 174.50(10) . . . . ?
N2 N3 C18 C19 84.71(14) . . . . ?
N2 N3 C18 C20 -148.48(11) . . . . ?
N2 N3 C21 C22 -101.6(12) . . . . ?
N2 N3 C21 C23 -66.75(18) . . . . ?
N2 N3 C21 C24 21.9(14) . . . . ?
N2 N3 C21 C25 57.75(15) . . . . ?
C1 O1 C2 O2 -179.87(10) . . . . ?
C1 O1 C2 C3 -2.09(15) . . . . ?
C1 N1 N2 N3 179.25(9) . . . . ?
C1 C5 C12 C13 -64.56(14) . . . . ?
C1 C5 C12 C17 112.03(12) . . . . ?
C2 O1 C1 N1 178.90(9) . . . . ?
C2 O1 C1 C5 -0.48(16) . . . . ?
C2 C3 C4 C5 0.58(17) . . . . ?
C2 C3 C4 C6 -174.61(11) . . . . ?
C3 C4 C5 C1 -3.09(16) . . . . ?
C3 C4 C5 C12 174.04(10) . . . . ?
C3 C4 C6 C7 -37.96(16) . . . . ?
C3 C4 C6 C11 136.13(11) . . . . ?
C4 C5 C12 C13 118.34(13) . . . . ?
C4 C5 C12 C17 -65.07(15) . . . . ?
C4 C6 C7 C8 171.75(11) . . . . ?
C4 C6 C11 C10 -172.40(10) . . . . ?
C5 C4 C6 C7 147.03(11) . . . . ?
C5 C4 C6 C11 -38.88(16) . . . . ?
C5 C12 C13 C14 175.81(11) . . . . ?
C5 C12 C17 C16 -175.52(11) . . . . ?
C6 C4 C5 C1 171.86(10) . . . . ?
C6 C4 C5 C12 -11.02(17) . . . . ?
C6 C7 C8 C9 1.3(2) . . . . ?
C7 C6 C11 C10 1.75(17) . . . . ?
C7 C8 C9 C10 0.6(2) . . . . ?
C8 C9 C10 C11 -1.38(19) . . . . ?
C9 C10 C11 C6 0.17(18) . . . . ?
C11 C6 C7 C8 -2.49(19) . . . . ?
C12 C13 C14 C15 -0.2(2) . . . . ?
C13 C12 C17 C16 1.12(18) . . . . ?
C13 C14 C15 C16 0.8(2) . . . . ?
C14 C15 C16 C17 -0.5(2) . . . . ?
C15 C16 C17 C12 -0.5(2) . . . . ?
C17 C12 C13 C14 -0.77(18) . . . . ?
C18 N3 C21 C22 68.3(12) . . . . ?
C18 N3 C21 C23 103.14(18) . . . . ?
C18 N3 C21 C24 -168.2(14) . . . . ?
C18 N3 C21 C25 -132.37(14) . . . . ?
C21 N3 C18 C19 -84.32(14) . . . . ?
C21 N3 C18 C20 42.50(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.974
_oxdiff_exptl_absorpt_empirical_full_min 0.618
####################################################################### 
# 
# 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_jft-r263
_database_code_depnum_ccdc_archive 'CCDC 2075641'
loop_
_audit_author_name
_audit_author_address
'Farzaneh Fadaei Tirani'
;EPFL ISIC
Switzerland
;
_audit_update_record             
;
2021-04-06 deposited with the CCDC.	2021-06-04 downloaded from the CCDC.
;
_audit_creation_date             2020-11-04
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H11 F O2'
_chemical_formula_sum            'C17 H11 F O2'
_chemical_formula_weight         266.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C17 H11 O2 F1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   6.12164(16)
_cell_length_b                   18.5825(5)
_cell_length_c                   11.3690(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.117(2)
_cell_angle_gamma                90
_cell_volume                     1283.32(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6150
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      76.5240
_cell_measurement_theta_min      4.5500
_shelx_estimated_absorpt_T_max   0.935
_shelx_estimated_absorpt_T_min   0.634
_exptl_absorpt_coefficient_mu    0.823
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.503
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear pale colourless'
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             552
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 2 0.0491
-2 1 0 0.3084
0 -10 -4 0.0610
0 9 5 0.0417
0 12 0 0.0415
0 -12 0 0.0415
0 0 -7 0.0557
0 0 7 0.0484
2 3 -6 0.1679
-3 -5 3 0.2659
-1 5 2 0.1530
0 -1 1 0.0441
0 1 -1 0.0498
3 -5 0 0.2423

_exptl_crystal_size_max          0.609
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.083
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0001 0.9995 1.9997 -0.0240 0.1264 -0.2548
-2.0002 1.0008 0.0015 -0.0518 0.4386 0.2627
0.2658 -10.0498 -4.0786 0.6926 -0.4236 0.5838
0.0916 9.1768 4.7262 -0.6089 0.3723 -0.7005
0.1252 12.0517 -0.1669 -0.9805 0.1286 -0.1488
-0.1252 -12.0517 0.1669 0.9805 -0.1286 0.1488
-0.0544 0.4355 -7.3051 -0.2416 -0.3943 0.8867
0.0399 -0.4545 7.3083 0.2435 0.3973 -0.8848
2.1579 3.2328 -6.3245 -0.4719 -0.7707 0.4280
-3.3865 -4.6208 3.3892 0.5187 0.8473 0.1141
-0.9995 5.0000 2.0002 -0.3328 0.3933 -0.1675
-0.0002 -1.0003 1.0000 0.1092 0.0428 -0.1085
0.0002 1.0003 -1.0000 -0.1092 -0.0428 0.1085
2.9998 -5.0013 -0.0020 0.3606 -0.7056 -0.3499

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14068
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.661
_diffrn_reflns_theta_min         4.585
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2665
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -98.00 -49.00   1.00    1.50    --  -43.01-165.00 -21.00   49
  2  ω    -84.00 -37.00   1.00    1.50    --  -43.01 116.00-145.00   47
  3  ω    -95.00 -70.00   1.00    1.50    --  -43.01 165.00   2.00   25
  4  ω     33.00  58.00   1.00    1.50    --   43.01-116.00 126.00   25
  5  ω     92.00 124.00   1.00    1.50    --   43.01-165.00 -21.00   32
  6  ω     73.00  98.00   1.00    6.00    --  112.00-116.00 126.00   25
  7  ω     76.00 101.00   1.00    6.00    --  112.00-165.00 -21.00   25
  8  ω     89.00 114.00   1.00    6.00    --  112.00 165.00   2.00   25
  9  ω    104.00 139.00   1.00    6.00    --  112.00 116.00-145.00   35
 10  ω    -53.00 -19.00   1.00    1.50    --  -43.01 -37.00 -60.00   34
 11  ω   -115.00 -58.00   1.00    1.50    --  -43.01 -37.00 -60.00   57
 12  ω    -31.00  67.00   1.00    1.50    --   43.01 -37.00-180.00   98
 13  ω     16.00  60.00   1.00    1.50    --   43.01 -37.00 -30.00   44
 14  ω    -21.00   4.00   1.00    1.50    --   43.01 -37.00 -30.00   25
 15  ω     13.00  66.00   1.00    1.50    --   43.01 -99.00 150.00   53
 16  ω    137.00 163.00   1.00    6.00    --  112.00 111.00-180.00   26
 17  ω     36.00 109.00   1.00    6.00    --  112.00-111.00 150.00   73
 18  ω    153.00 178.00   1.00    6.00    --  112.00  61.00-180.00   25
 19  ω    109.00 175.00   1.00    6.00    --  112.00  77.00  60.00   66
 20  ω     62.00 101.00   1.00    6.00    --  112.00-111.00 -60.00   39
 21  ω     69.00 109.00   1.00    6.00    --  112.00-111.00-150.00   40
 22  ω     32.00  67.00   1.00    6.00    --  112.00 -94.00 120.00   35
 23  ω     63.00  96.00   1.00    6.00    --  112.00-111.00 -30.00   33
 24  ω    109.00 178.00   1.00    6.00    --  112.00 111.00 -90.00   69
 25  ω     30.00  64.00   1.00    6.00    --  112.00 -94.00 -30.00   34
 26  ω     98.00 174.00   1.00    6.00    --  112.00  45.00  30.00   76
 27  ω     59.00  85.00   1.00    6.00    --  112.00-111.00  60.00   26
 28  ω    104.00 171.00   1.00    6.00    --  112.00 111.00 120.00   67
 29  ω    107.00 177.00   1.00    6.00    --  112.00  45.00   0.00   70
 30  ω     39.00 106.00   1.00    6.00    --  112.00 -45.00 120.00   67
 31  ω     73.00  99.00   1.00    6.00    --  112.00-111.00-120.00   26
 32  ω    110.00 150.00   1.00    6.00    --  112.00  77.00 -90.00   40
 33  ω     46.00 109.00   1.00    6.00    --  112.00-111.00   0.00   63
 34  ω     37.00  62.00   1.00    6.00    --  112.00-111.00  90.00   25
 35  ω     65.00 106.00   1.00    6.00    --  112.00-111.00  90.00   41
 36  ω    103.00 128.00   1.00    6.00    --  112.00  61.00-180.00   25
 37  ω     82.00 107.00   1.00    6.00    --  112.00 -94.00 120.00   25
 38  ω     77.00 108.00   1.00    6.00    --  112.00-111.00  30.00   31
 39  ω     42.00 109.00   1.00    6.00    --  112.00-111.00 -90.00   67
 40  ω    125.00 165.00   1.00    6.00    --  112.00 111.00 150.00   40
 41  ω    106.00 152.00   1.00    6.00    --  112.00  77.00 120.00   46
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0145070000
_diffrn_orient_matrix_UB_12      -0.0808125000
_diffrn_orient_matrix_UB_13      0.0283651000
_diffrn_orient_matrix_UB_21      -0.2124182000
_diffrn_orient_matrix_UB_22      0.0136544000
_diffrn_orient_matrix_UB_23      0.0563713000
_diffrn_orient_matrix_UB_31      -0.1377147000
_diffrn_orient_matrix_UB_32      -0.0125896000
_diffrn_orient_matrix_UB_33      -0.1211002000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2402
_reflns_number_total             2685
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0020(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2685
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0328
_refine_ls_restrained_S_all      1.035
_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)+(0.0524P)²+0.1936P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.0920
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.48244(15) 0.92757(4) 0.55558(7) 0.0491(2) Uani 1 1 d . . . . .
O1 O 0.62955(14) 0.83856(4) 0.66147(7) 0.0382(2) Uani 1 1 d . . . . .
O2 O 0.80297(14) 0.75240(5) 0.77076(7) 0.0431(2) Uani 1 1 d . . . . .
C1 C 0.4630(2) 0.85839(6) 0.58163(10) 0.0363(2) Uani 1 1 d . . . . .
C2 C 0.64235(18) 0.76687(6) 0.70285(9) 0.0332(2) Uani 1 1 d . . . . .
C3 C 0.46214(16) 0.71940(6) 0.65874(8) 0.0289(2) Uani 1 1 d . . . . .
C4 C 0.30168(16) 0.74254(6) 0.57188(8) 0.0282(2) Uani 1 1 d . . . . .
C5 C 0.30234(19) 0.81620(6) 0.53242(9) 0.0339(2) Uani 1 1 d . . . . .
H5 H 0.197(2) 0.8349(8) 0.4713(13) 0.039(4) Uiso 1 1 d . . . . .
C6 C 0.46717(16) 0.64785(6) 0.71713(8) 0.0293(2) Uani 1 1 d . . . . .
C7 C 0.64714(18) 0.60188(7) 0.71694(9) 0.0354(2) Uani 1 1 d . . . . .
H7 H 0.770(3) 0.6162(8) 0.6756(14) 0.046(4) Uiso 1 1 d . . . . .
C8 C 0.6516(2) 0.53631(7) 0.77589(10) 0.0413(3) Uani 1 1 d . . . . .
H8 H 0.778(3) 0.5043(9) 0.7770(15) 0.058(5) Uiso 1 1 d . . . . .
C9 C 0.4777(2) 0.51623(7) 0.83620(10) 0.0420(3) Uani 1 1 d . . . . .
H9 H 0.485(3) 0.4706(9) 0.8800(15) 0.051(4) Uiso 1 1 d . . . . .
C10 C 0.2980(2) 0.56168(7) 0.83641(10) 0.0399(3) Uani 1 1 d . . . . .
H10 H 0.173(3) 0.5475(9) 0.8771(15) 0.052(4) Uiso 1 1 d . . . . .
C11 C 0.29193(18) 0.62725(6) 0.77736(9) 0.0328(2) Uani 1 1 d . . . . .
H11 H 0.162(3) 0.6600(8) 0.7757(13) 0.041(4) Uiso 1 1 d . . . . .
C12 C 0.12709(16) 0.69502(6) 0.51209(8) 0.0278(2) Uani 1 1 d . . . . .
C13 C -0.08246(17) 0.72297(6) 0.47637(9) 0.0328(2) Uani 1 1 d . . . . .
H13 H -0.116(2) 0.7721(8) 0.4941(13) 0.036(3) Uiso 1 1 d . . . . .
C14 C -0.24538(19) 0.68061(8) 0.41438(10) 0.0410(3) Uani 1 1 d . . . . .
H14 H -0.387(3) 0.7013(10) 0.3887(16) 0.058(5) Uiso 1 1 d . . . . .
C15 C -0.2001(2) 0.61016(8) 0.38721(10) 0.0433(3) Uani 1 1 d . . . . .
H15 H -0.313(3) 0.5796(9) 0.3437(15) 0.054(4) Uiso 1 1 d . . . . .
C16 C 0.0079(2) 0.58183(7) 0.42074(10) 0.0385(3) Uani 1 1 d . . . . .
H16 H 0.042(3) 0.5322(9) 0.4009(14) 0.049(4) Uiso 1 1 d . . . . .
C17 C 0.17098(18) 0.62397(6) 0.48281(9) 0.0317(2) Uani 1 1 d . . . . .
H17 H 0.319(2) 0.6042(8) 0.5041(12) 0.036(3) Uiso 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
F1 C1 1.3280(13) . ?
O1 C1 1.3305(15) . ?
O1 C2 1.4119(14) . ?
O2 C2 1.2030(14) . ?
C1 C5 1.3259(16) . ?
C2 C3 1.4523(14) . ?
C3 C4 1.3728(14) . ?
C3 C6 1.4847(14) . ?
C4 C5 1.4407(14) . ?
C4 C12 1.4846(14) . ?
C6 C7 1.3944(15) . ?
C6 C11 1.3959(15) . ?
C7 C8 1.3892(17) . ?
C8 C9 1.387(2) . ?
C9 C10 1.3870(19) . ?
C10 C11 1.3894(16) . ?
C12 C13 1.3968(14) . ?
C12 C17 1.3959(15) . ?
C13 C14 1.3917(16) . ?
C14 C15 1.381(2) . ?
C15 C16 1.3872(18) . ?
C16 C17 1.3901(15) . ?

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 O1 C2 119.66(8) . . ?
F1 C1 O1 109.74(10) . . ?
C5 C1 F1 124.10(11) . . ?
C5 C1 O1 126.14(11) . . ?
O1 C2 C3 116.72(9) . . ?
O2 C2 O1 115.59(10) . . ?
O2 C2 C3 127.70(11) . . ?
C2 C3 C6 114.62(9) . . ?
C4 C3 C2 120.23(10) . . ?
C4 C3 C6 125.13(9) . . ?
C3 C4 C5 119.48(9) . . ?
C3 C4 C12 123.61(9) . . ?
C5 C4 C12 116.88(9) . . ?
C1 C5 C4 117.45(10) . . ?
C7 C6 C3 121.38(10) . . ?
C7 C6 C11 119.21(10) . . ?
C11 C6 C3 119.37(10) . . ?
C8 C7 C6 120.33(11) . . ?
C9 C8 C7 120.27(11) . . ?
C10 C9 C8 119.63(11) . . ?
C9 C10 C11 120.46(11) . . ?
C10 C11 C6 120.10(11) . . ?
C13 C12 C4 119.68(9) . . ?
C17 C12 C4 121.52(9) . . ?
C17 C12 C13 118.64(10) . . ?
C14 C13 C12 120.77(11) . . ?
C15 C14 C13 119.89(11) . . ?
C14 C15 C16 120.07(10) . . ?
C15 C16 C17 120.18(11) . . ?
C16 C17 C12 120.43(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C1 C5 C4 -178.81(10) . . . . ?
O1 C1 C5 C4 2.62(18) . . . . ?
O1 C2 C3 C4 6.55(14) . . . . ?
O1 C2 C3 C6 -171.92(8) . . . . ?
O2 C2 C3 C4 -173.27(11) . . . . ?
O2 C2 C3 C6 8.27(16) . . . . ?
C1 O1 C2 O2 176.73(10) . . . . ?
C1 O1 C2 C3 -3.10(14) . . . . ?
C2 O1 C1 F1 179.78(9) . . . . ?
C2 O1 C1 C5 -1.49(17) . . . . ?
C2 C3 C4 C5 -5.57(15) . . . . ?
C2 C3 C4 C12 172.59(9) . . . . ?
C2 C3 C6 C7 -58.04(13) . . . . ?
C2 C3 C6 C11 119.48(10) . . . . ?
C3 C4 C5 C1 1.06(15) . . . . ?
C3 C4 C12 C13 146.16(10) . . . . ?
C3 C4 C12 C17 -38.48(15) . . . . ?
C3 C6 C7 C8 177.63(10) . . . . ?
C3 C6 C11 C10 -177.48(9) . . . . ?
C4 C3 C6 C7 123.58(12) . . . . ?
C4 C3 C6 C11 -58.89(14) . . . . ?
C4 C12 C13 C14 176.44(10) . . . . ?
C4 C12 C17 C16 -176.26(10) . . . . ?
C5 C4 C12 C13 -35.64(14) . . . . ?
C5 C4 C12 C17 139.72(10) . . . . ?
C6 C3 C4 C5 172.72(9) . . . . ?
C6 C3 C4 C12 -9.12(16) . . . . ?
C6 C7 C8 C9 -0.47(17) . . . . ?
C7 C6 C11 C10 0.11(15) . . . . ?
C7 C8 C9 C10 0.63(18) . . . . ?
C8 C9 C10 C11 -0.43(18) . . . . ?
C9 C10 C11 C6 0.06(17) . . . . ?
C11 C6 C7 C8 0.10(16) . . . . ?
C12 C4 C5 C1 -177.22(10) . . . . ?
C12 C13 C14 C15 -0.26(17) . . . . ?
C13 C12 C17 C16 -0.86(15) . . . . ?
C13 C14 C15 C16 -0.54(18) . . . . ?
C14 C15 C16 C17 0.64(18) . . . . ?
C15 C16 C17 C12 0.08(17) . . . . ?
C17 C12 C13 C14 0.95(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 2.092
_oxdiff_exptl_absorpt_empirical_full_min 0.679
####################################################################### 
# 
# 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_jft-r348
_database_code_depnum_ccdc_archive 'CCDC 2075645'
loop_
_audit_author_name
_audit_author_address
'Farzaneh Fadaei Tirani'
;EPFL ISIC
Switzerland
;
_audit_update_record             
;
2021-04-06 deposited with the CCDC.	2021-06-04 downloaded from the CCDC.
;
_audit_creation_date             2020-12-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H21 N3 O2'
_chemical_formula_sum            'C18 H21 N3 O2'
_chemical_formula_weight         311.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H21 N3 O2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   10.40586(17)
_cell_length_b                   28.8016(4)
_cell_length_c                   11.4833(2)
_cell_angle_alpha                90
_cell_angle_beta                 109.1940(18)
_cell_angle_gamma                90
_cell_volume                     3250.29(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    10150
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      72.6240
_cell_measurement_theta_min      4.7430
_shelx_estimated_absorpt_T_max   0.940
_shelx_estimated_absorpt_T_min   0.758
_exptl_absorpt_coefficient_mu    0.679
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.600
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear pale colourless'
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1328
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.0507
0 -1 0 0.0607
2 0 -1 0.1902
-2 0 1 0.2209
0 -2 -1 0.0756
0 -1 -2 0.0716
1 -1 -1 0.1573
2 -1 2 0.1701
0 -1 1 0.0619
0 2 -1 0.0343
5 11 0 0.1606
0 7 7 0.0596
0 -11 6 0.0570

_exptl_crystal_size_max          0.431
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.093
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0000 1.0002 -0.0002 -0.0501 -0.0067 -0.0176
0.0000 -1.0002 0.0002 0.0501 0.0067 0.0176
2.0006 0.0015 -1.0004 -0.0886 -0.0665 0.2774
-2.0006 -0.0015 1.0004 0.0886 0.0665 -0.2774
0.0000 -2.0005 -0.9997 0.0678 0.1455 0.0766
0.0000 -1.0006 -2.0001 -0.0146 0.2708 0.1003
1.0003 -0.9995 -1.0001 -0.0104 0.0395 0.1770
2.0006 -0.9981 2.0002 0.0584 -0.4559 0.1710
0.0000 -1.0000 1.0004 0.0824 -0.1253 -0.0237
-0.0000 2.0002 -1.0006 -0.1324 0.1185 0.0061
5.0015 11.0062 -0.0029 -0.6915 -0.5705 0.3965
-0.0001 7.0025 6.9996 -0.1243 -0.9713 -0.4127
0.0000 -11.0008 6.0031 0.7446 -0.7180 -0.0543

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8186
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.781
_diffrn_reflns_theta_min         3.069
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2817
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -66.00  12.00   1.00    5.00    --  -40.91  98.00-118.00   78
  2  ω     20.00  79.00   1.00    5.00    --   40.91 -98.00 134.00   59
  3  ω    114.00 161.00   1.00   20.00    --  105.15  98.00-118.00   47
  4  ω     56.00 107.00   1.00   20.00    --  105.15 -98.00 134.00   51
  5  ω      4.00  31.00   1.00    5.00    --  -40.91  38.00  30.00   27
  6  ω    -42.00 -16.00   1.00    5.00    --  -40.91  38.00  30.00   26
  7  ω   -111.00 -16.00   1.00    5.00    --  -40.91 -38.00  90.00   95
  8  ω   -113.00 -17.00   1.00    5.00    --  -40.91 -57.00   0.00   96
  9  ω     88.00 113.00   1.00    5.00    --   40.91  57.00  30.00   25
 10  ω     52.00 105.00   1.00   20.00    --  105.15 -94.00-150.00   53
 11  ω    108.00 133.00   1.00   20.00    --  105.15 -61.00 120.00   25
 12  ω     28.00 105.00   1.00   20.00    --  105.15 -94.00 -60.00   77
 13  ω     33.00  87.00   1.00   20.00    --  105.15 -61.00 120.00   54
 14  ω     26.00  72.00   1.00   20.00    --  105.15 -94.00  30.00   46
 15  ω    104.00 177.00   1.00   20.00    --  105.15 111.00-180.00   73
 16  ω    103.00 154.00   1.00   20.00    --  105.15  77.00 -30.00   51
 17  ω    105.00 134.00   1.00   20.00    --  105.15 111.00 -30.00   29
 18  ω     37.00  63.00   1.00   20.00    --  105.15-111.00 -60.00   26
 19  ω     84.00 109.00   1.00   20.00    --  105.15-111.00 -30.00   25
 20  ω    105.00 174.00   1.00   20.00    --  105.15 111.00-150.00   69
 21  ω     80.00 178.00   1.00   20.00    --  105.15  45.00 -60.00   98
 22  ω     43.00 133.00   1.00   20.00    --  105.15 -30.00 120.00   90
 23  ω     72.00 109.00   1.00   20.00    --  105.15-111.00  60.00   37
 24  ω     34.00 129.00   1.00   20.00    --  105.15 -45.00 -90.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0280882000
_diffrn_orient_matrix_UB_12      -0.0500528000
_diffrn_orient_matrix_UB_13      0.0323177000
_diffrn_orient_matrix_UB_21      -0.0992574000
_diffrn_orient_matrix_UB_22      -0.0067633000
_diffrn_orient_matrix_UB_23      -0.1319995000
_diffrn_orient_matrix_UB_31      0.1180218000
_diffrn_orient_matrix_UB_32      -0.0176191000
_diffrn_orient_matrix_UB_33      -0.0413341000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7212
_reflns_number_total             8186
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.0017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     586
_refine_ls_number_reflns         8186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0371
_refine_ls_restrained_S_all      1.068
_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)+(0.0856P)²+0.0670P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1136
_refine_special_details          
;
 Refined as a 3-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.5832(16)
 0.3779(13) 0.0389(9)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.04678(11) 0.38842(4) 0.01126(10) 0.0356(3) Uani 1 1 d . . . . .
O2 O 1.06160(9) 0.36245(3) 0.19651(9) 0.0250(2) Uani 1 1 d . . . . .
N1 N 1.06211(11) 0.33540(4) 0.38648(10) 0.0232(2) Uani 1 1 d . . . . .
N2 N 0.96200(11) 0.33313(4) 0.44045(10) 0.0222(2) Uani 1 1 d . . . . .
N3 N 0.98726(11) 0.31535(4) 0.55925(10) 0.0222(2) Uani 1 1 d . . . . .
C1 C 0.98695(14) 0.38183(4) 0.08360(13) 0.0254(3) Uani 1 1 d . . . . .
C2 C 0.84428(14) 0.39209(5) 0.06158(12) 0.0251(3) Uani 1 1 d . . . . .
H2 H 0.7974(18) 0.4040(6) -0.0214(17) 0.030(4) Uiso 1 1 d . . . . .
C3 C 0.77833(13) 0.38451(4) 0.14416(12) 0.0212(3) Uani 1 1 d . . . . .
C4 C 0.85809(13) 0.36368(4) 0.25947(12) 0.0207(3) Uani 1 1 d . . . . .
C5 C 0.99569(13) 0.35376(4) 0.27845(12) 0.0211(3) Uani 1 1 d . . . . .
C6 C 0.84138(13) 0.35010(4) 0.36971(12) 0.0215(3) Uani 1 1 d . . . . .
H6 H 0.7693(17) 0.3524(5) 0.4011(15) 0.021(4) Uiso 1 1 d . . . . .
C7 C 0.63230(13) 0.39664(4) 0.11338(11) 0.0219(3) Uani 1 1 d . . . . .
C8 C 0.57788(15) 0.43278(5) 0.03083(13) 0.0275(3) Uani 1 1 d . . . . .
H8 H 0.635(2) 0.4530(7) -0.003(2) 0.045(5) Uiso 1 1 d . . . . .
C9 C 0.43915(15) 0.44211(5) -0.00757(14) 0.0319(3) Uani 1 1 d . . . . .
H9 H 0.405(2) 0.4678(7) -0.065(2) 0.041(5) Uiso 1 1 d . . . . .
C10 C 0.35377(15) 0.41638(5) 0.03781(14) 0.0314(3) Uani 1 1 d . . . . .
H10 H 0.260(2) 0.4215(7) 0.012(2) 0.043(5) Uiso 1 1 d . . . . .
C11 C 0.40684(15) 0.38109(5) 0.12179(14) 0.0308(3) Uani 1 1 d . . . . .
H11 H 0.346(2) 0.3625(7) 0.1539(19) 0.040(5) Uiso 1 1 d . . . . .
C12 C 0.54544(14) 0.37103(5) 0.15958(12) 0.0255(3) Uani 1 1 d . . . . .
H12 H 0.5826(19) 0.3455(6) 0.2177(17) 0.030(4) Uiso 1 1 d . . . . .
C13 C 1.01411(14) 0.26435(4) 0.56291(13) 0.0255(3) Uani 1 1 d . . . . .
H13 H 1.0111(18) 0.2538(6) 0.6444(18) 0.030(4) Uiso 1 1 d . . . . .
C14 C 0.89924(17) 0.24059(5) 0.46374(17) 0.0361(3) Uani 1 1 d . . . . .
H14A H 0.812(3) 0.2510(8) 0.471(2) 0.053(6) Uiso 1 1 d . . . . .
H14B H 0.908(2) 0.2065(8) 0.474(2) 0.047(5) Uiso 1 1 d . . . . .
H14C H 0.902(2) 0.2489(7) 0.380(2) 0.050(6) Uiso 1 1 d . . . . .
C15 C 1.15258(16) 0.24968(5) 0.55612(17) 0.0345(3) Uani 1 1 d . . . . .
H15A H 1.161(2) 0.2566(8) 0.478(2) 0.052(6) Uiso 1 1 d . . . . .
H15B H 1.166(2) 0.2162(8) 0.568(2) 0.046(6) Uiso 1 1 d . . . . .
H15C H 1.227(3) 0.2651(9) 0.621(3) 0.065(7) Uiso 1 1 d . . . . .
C16 C 1.0490(2) 0.39444(5) 0.63900(17) 0.0409(4) Uani 1 1 d . . . . .
H16A H 0.965(2) 0.3974(8) 0.659(2) 0.050(6) Uiso 1 1 d . . . . .
H16B H 1.032(2) 0.4058(7) 0.554(2) 0.041(5) Uiso 1 1 d . . . . .
H16C H 1.120(2) 0.4132(8) 0.695(2) 0.047(5) Uiso 1 1 d . . . . .
C17 C 1.09326(14) 0.34393(5) 0.64972(13) 0.0272(3) Uani 1 1 d . . . . .
H17 H 1.181(2) 0.3415(7) 0.6298(19) 0.041(5) Uiso 1 1 d . . . . .
C18 C 1.11325(17) 0.32635(6) 0.77948(14) 0.0352(3) Uani 1 1 d . . . . .
H18A H 1.177(2) 0.3472(8) 0.840(2) 0.052(6) Uiso 1 1 d . . . . .
H18B H 1.029(3) 0.3265(7) 0.796(2) 0.053(6) Uiso 1 1 d . . . . .
H18C H 1.154(2) 0.2940(7) 0.7956(19) 0.042(5) Uiso 1 1 d . . . . .
O3 O 0.66044(11) 0.51610(4) 0.31530(10) 0.0339(2) Uani 1 1 d . . . . .
O4 O 0.64040(9) 0.45134(3) 0.41203(9) 0.0256(2) Uani 1 1 d . . . . .
N4 N 0.60407(11) 0.38369(4) 0.50636(11) 0.0239(2) Uani 1 1 d . . . . .
N5 N 0.48812(11) 0.36501(4) 0.52096(10) 0.0219(2) Uani 1 1 d . . . . .
N6 N 0.48960(11) 0.32161(4) 0.57710(10) 0.0225(2) Uani 1 1 d . . . . .
C19 C 0.58332(14) 0.49072(5) 0.34429(13) 0.0250(3) Uani 1 1 d . . . . .
C20 C 0.43825(14) 0.49827(4) 0.31488(12) 0.0242(3) Uani 1 1 d . . . . .
H20 H 0.4079(17) 0.5268(6) 0.2727(16) 0.025(4) Uiso 1 1 d . . . . .
C21 C 0.35318(13) 0.46917(4) 0.34788(11) 0.0211(3) Uani 1 1 d . . . . .
C22 C 0.41553(12) 0.42929(4) 0.41911(11) 0.0203(3) Uani 1 1 d . . . . .
C23 C 0.55609(13) 0.42220(4) 0.44602(12) 0.0217(3) Uani 1 1 d . . . . .
C24 C 0.37519(12) 0.39031(4) 0.46937(12) 0.0211(3) Uani 1 1 d . . . . .
H24 H 0.2908(18) 0.3798(6) 0.4720(15) 0.023(4) Uiso 1 1 d . . . . .
C25 C 0.20499(13) 0.47819(4) 0.30957(12) 0.0222(3) Uani 1 1 d . . . . .
C26 C 0.13940(14) 0.49855(5) 0.19501(13) 0.0269(3) Uani 1 1 d . . . . .
H26 H 0.192(2) 0.5056(6) 0.1361(18) 0.034(4) Uiso 1 1 d . . . . .
C27 C 0.00045(15) 0.50758(5) 0.15732(14) 0.0315(3) Uani 1 1 d . . . . .
H27 H -0.043(2) 0.5218(7) 0.0791(19) 0.038(5) Uiso 1 1 d . . . . .
C28 C -0.07400(14) 0.49582(5) 0.23357(14) 0.0284(3) Uani 1 1 d . . . . .
H28 H -0.169(2) 0.5010(7) 0.208(2) 0.049(6) Uiso 1 1 d . . . . .
C29 C -0.00974(14) 0.47584(5) 0.34790(14) 0.0263(3) Uani 1 1 d . . . . .
H29 H -0.060(2) 0.4694(6) 0.4022(18) 0.032(4) Uiso 1 1 d . . . . .
C30 C 0.12949(14) 0.46700(4) 0.38603(13) 0.0238(3) Uani 1 1 d . . . . .
H30 H 0.1732(18) 0.4546(6) 0.4694(16) 0.025(4) Uiso 1 1 d . . . . .
C31 C 0.53001(15) 0.28530(5) 0.50397(14) 0.0283(3) Uani 1 1 d . . . . .
H31 H 0.6208(18) 0.2926(6) 0.4990(16) 0.025(4) Uiso 1 1 d . . . . .
C32 C 0.42820(19) 0.28542(5) 0.37426(15) 0.0370(4) Uani 1 1 d . . . . .
H32A H 0.432(2) 0.3148(7) 0.3333(18) 0.036(5) Uiso 1 1 d . . . . .
H32B H 0.334(2) 0.2818(7) 0.377(2) 0.049(6) Uiso 1 1 d . . . . .
H32C H 0.448(2) 0.2611(7) 0.325(2) 0.043(5) Uiso 1 1 d . . . . .
C33 C 0.53287(18) 0.23771(5) 0.56368(17) 0.0361(3) Uani 1 1 d . . . . .
H33A H 0.544(2) 0.2146(7) 0.509(2) 0.045(5) Uiso 1 1 d . . . . .
H33B H 0.604(2) 0.2343(7) 0.639(2) 0.040(5) Uiso 1 1 d . . . . .
H33C H 0.444(2) 0.2301(7) 0.578(2) 0.047(5) Uiso 1 1 d . . . . .
C34 C 0.56714(15) 0.32288(5) 0.71155(13) 0.0281(3) Uani 1 1 d . . . . .
H34 H 0.5456(19) 0.2919(6) 0.7431(17) 0.032(4) Uiso 1 1 d . . . . .
C35 C 0.50756(17) 0.35981(6) 0.77292(14) 0.0348(3) Uani 1 1 d . . . . .
H35A H 0.547(2) 0.3572(7) 0.863(2) 0.049(6) Uiso 1 1 d . . . . .
H35B H 0.409(2) 0.3564(7) 0.751(2) 0.045(5) Uiso 1 1 d . . . . .
H35C H 0.527(2) 0.3912(8) 0.746(2) 0.049(6) Uiso 1 1 d . . . . .
C36 C 0.72127(16) 0.32833(7) 0.74632(17) 0.0405(4) Uani 1 1 d . . . . .
H36A H 0.746(2) 0.3607(7) 0.724(2) 0.045(5) Uiso 1 1 d . . . . .
H36B H 0.760(3) 0.3243(8) 0.834(2) 0.056(6) Uiso 1 1 d . . . . .
H36C H 0.758(2) 0.3050(8) 0.701(2) 0.052(6) Uiso 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
O1 C1 1.2057(18) . ?
O2 C1 1.3906(17) . ?
O2 C5 1.3574(16) . ?
N1 N2 1.3776(15) . ?
N1 C5 1.3163(17) . ?
N2 N3 1.3989(15) . ?
N2 C6 1.3430(16) . ?
N3 C13 1.4932(16) . ?
N3 C17 1.4900(17) . ?
C1 C2 1.4520(19) . ?
C2 C3 1.3586(19) . ?
C3 C4 1.4421(18) . ?
C3 C7 1.4842(18) . ?
C4 C5 1.4050(17) . ?
C4 C6 1.3895(18) . ?
C7 C8 1.3963(18) . ?
C7 C12 1.3993(19) . ?
C8 C9 1.390(2) . ?
C9 C10 1.384(2) . ?
C10 C11 1.385(2) . ?
C11 C12 1.393(2) . ?
C13 C14 1.516(2) . ?
C13 C15 1.528(2) . ?
C16 C17 1.519(2) . ?
C17 C18 1.522(2) . ?
O3 C19 1.2102(17) . ?
O4 C19 1.3930(16) . ?
O4 C23 1.3608(15) . ?
N4 N5 1.3808(15) . ?
N4 C23 1.3161(17) . ?
N5 N6 1.4041(14) . ?
N5 C24 1.3436(16) . ?
N6 C31 1.4859(17) . ?
N6 C34 1.4890(17) . ?
C19 C20 1.4509(19) . ?
C20 C21 1.3602(18) . ?
C21 C22 1.4355(17) . ?
C21 C25 1.4808(17) . ?
C22 C23 1.4068(17) . ?
C22 C24 1.3889(17) . ?
C25 C26 1.3965(19) . ?
C25 C30 1.3947(19) . ?
C26 C27 1.3908(19) . ?
C27 C28 1.388(2) . ?
C28 C29 1.387(2) . ?
C29 C30 1.3923(19) . ?
C31 C32 1.518(2) . ?
C31 C33 1.5286(19) . ?
C34 C35 1.516(2) . ?
C34 C36 1.528(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O2 C1 117.75(10) . . ?
C5 N1 N2 101.69(10) . . ?
N1 N2 N3 121.91(10) . . ?
C6 N2 N1 113.91(10) . . ?
C6 N2 N3 124.17(11) . . ?
N2 N3 C13 111.17(10) . . ?
N2 N3 C17 109.65(10) . . ?
C17 N3 C13 115.79(10) . . ?
O1 C1 O2 116.67(12) . . ?
O1 C1 C2 125.31(13) . . ?
O2 C1 C2 118.02(11) . . ?
C3 C2 C1 124.60(12) . . ?
C2 C3 C4 115.94(12) . . ?
C2 C3 C7 120.57(12) . . ?
C4 C3 C7 123.49(11) . . ?
C5 C4 C3 118.46(11) . . ?
C6 C4 C3 138.34(12) . . ?
C6 C4 C5 103.17(11) . . ?
O2 C5 C4 125.20(12) . . ?
N1 C5 O2 119.93(11) . . ?
N1 C5 C4 114.86(11) . . ?
N2 C6 C4 106.35(11) . . ?
C8 C7 C3 119.48(12) . . ?
C8 C7 C12 118.82(12) . . ?
C12 C7 C3 121.60(11) . . ?
C9 C8 C7 120.43(13) . . ?
C10 C9 C8 120.37(13) . . ?
C9 C10 C11 119.80(13) . . ?
C10 C11 C12 120.30(14) . . ?
C11 C12 C7 120.25(13) . . ?
N3 C13 C14 109.20(11) . . ?
N3 C13 C15 116.20(11) . . ?
C14 C13 C15 111.13(13) . . ?
N3 C17 C16 109.71(12) . . ?
N3 C17 C18 109.30(11) . . ?
C16 C17 C18 109.76(13) . . ?
C23 O4 C19 117.75(10) . . ?
C23 N4 N5 101.35(10) . . ?
N4 N5 N6 121.63(10) . . ?
C24 N5 N4 114.06(10) . . ?
C24 N5 N6 124.14(11) . . ?
N5 N6 C31 109.24(10) . . ?
N5 N6 C34 112.01(10) . . ?
C31 N6 C34 116.47(11) . . ?
O3 C19 O4 116.47(12) . . ?
O3 C19 C20 125.36(13) . . ?
O4 C19 C20 118.17(11) . . ?
C21 C20 C19 124.43(12) . . ?
C20 C21 C22 115.99(12) . . ?
C20 C21 C25 121.25(12) . . ?
C22 C21 C25 122.75(11) . . ?
C23 C22 C21 118.93(11) . . ?
C24 C22 C21 137.89(12) . . ?
C24 C22 C23 103.06(11) . . ?
O4 C23 C22 124.70(11) . . ?
N4 C23 O4 120.13(11) . . ?
N4 C23 C22 115.15(11) . . ?
N5 C24 C22 106.35(11) . . ?
C26 C25 C21 119.48(12) . . ?
C30 C25 C21 121.31(12) . . ?
C30 C25 C26 119.21(12) . . ?
C27 C26 C25 120.52(13) . . ?
C28 C27 C26 119.79(13) . . ?
C29 C28 C27 120.18(13) . . ?
C28 C29 C30 120.09(13) . . ?
C29 C30 C25 120.21(12) . . ?
N6 C31 C32 108.49(12) . . ?
N6 C31 C33 110.19(12) . . ?
C32 C31 C33 110.28(13) . . ?
N6 C34 C35 109.52(11) . . ?
N6 C34 C36 115.96(13) . . ?
C35 C34 C36 111.15(13) . . ?

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
O1 C1 C2 C3 -179.91(13) . . . . ?
O2 C1 C2 C3 0.7(2) . . . . ?
N1 N2 N3 C13 -68.22(14) . . . . ?
N1 N2 N3 C17 61.11(15) . . . . ?
N1 N2 C6 C4 1.66(15) . . . . ?
N2 N1 C5 O2 178.98(10) . . . . ?
N2 N1 C5 C4 0.19(14) . . . . ?
N2 N3 C13 C14 -52.59(15) . . . . ?
N2 N3 C13 C15 74.05(15) . . . . ?
N2 N3 C17 C16 55.82(15) . . . . ?
N2 N3 C17 C18 176.22(11) . . . . ?
N3 N2 C6 C4 -179.43(11) . . . . ?
C1 O2 C5 N1 179.94(11) . . . . ?
C1 O2 C5 C4 -1.41(18) . . . . ?
C1 C2 C3 C4 -1.66(19) . . . . ?
C1 C2 C3 C7 179.37(12) . . . . ?
C2 C3 C4 C5 1.14(17) . . . . ?
C2 C3 C4 C6 178.71(14) . . . . ?
C2 C3 C7 C8 -28.51(18) . . . . ?
C2 C3 C7 C12 147.77(13) . . . . ?
C3 C4 C5 O2 0.37(18) . . . . ?
C3 C4 C5 N1 179.09(11) . . . . ?
C3 C4 C6 N2 -179.18(14) . . . . ?
C3 C7 C8 C9 174.39(13) . . . . ?
C3 C7 C12 C11 -175.21(13) . . . . ?
C4 C3 C7 C8 152.60(12) . . . . ?
C4 C3 C7 C12 -31.13(18) . . . . ?
C5 O2 C1 O1 -178.59(11) . . . . ?
C5 O2 C1 C2 0.89(17) . . . . ?
C5 N1 N2 N3 179.91(11) . . . . ?
C5 N1 N2 C6 -1.16(14) . . . . ?
C5 C4 C6 N2 -1.37(13) . . . . ?
C6 N2 N3 C13 112.97(13) . . . . ?
C6 N2 N3 C17 -117.71(13) . . . . ?
C6 C4 C5 O2 -177.97(11) . . . . ?
C6 C4 C5 N1 0.75(15) . . . . ?
C7 C3 C4 C5 -179.92(11) . . . . ?
C7 C3 C4 C6 -2.3(2) . . . . ?
C7 C8 C9 C10 1.5(2) . . . . ?
C8 C7 C12 C11 1.1(2) . . . . ?
C8 C9 C10 C11 -0.1(2) . . . . ?
C9 C10 C11 C12 -0.8(2) . . . . ?
C10 C11 C12 C7 0.3(2) . . . . ?
C12 C7 C8 C9 -2.0(2) . . . . ?
C13 N3 C17 C16 -177.41(12) . . . . ?
C13 N3 C17 C18 -57.01(15) . . . . ?
C17 N3 C13 C14 -178.59(12) . . . . ?
C17 N3 C13 C15 -51.95(17) . . . . ?
O3 C19 C20 C21 179.68(13) . . . . ?
O4 C19 C20 C21 -0.7(2) . . . . ?
N4 N5 N6 C31 -61.13(15) . . . . ?
N4 N5 N6 C34 69.43(15) . . . . ?
N4 N5 C24 C22 -1.64(15) . . . . ?
N5 N4 C23 O4 -179.50(11) . . . . ?
N5 N4 C23 C22 -0.85(15) . . . . ?
N5 N6 C31 C32 -59.40(14) . . . . ?
N5 N6 C31 C33 179.78(12) . . . . ?
N5 N6 C34 C35 56.63(15) . . . . ?
N5 N6 C34 C36 -70.12(15) . . . . ?
N6 N5 C24 C22 -177.01(11) . . . . ?
C19 O4 C23 N4 177.62(12) . . . . ?
C19 O4 C23 C22 -0.90(18) . . . . ?
C19 C20 C21 C22 1.6(2) . . . . ?
C19 C20 C21 C25 -177.22(12) . . . . ?
C20 C21 C22 C23 -2.04(18) . . . . ?
C20 C21 C22 C24 -177.26(15) . . . . ?
C20 C21 C25 C26 34.24(19) . . . . ?
C20 C21 C25 C30 -145.36(13) . . . . ?
C21 C22 C23 O4 1.82(19) . . . . ?
C21 C22 C23 N4 -176.76(11) . . . . ?
C21 C22 C24 N5 176.68(15) . . . . ?
C21 C25 C26 C27 -179.65(13) . . . . ?
C21 C25 C30 C29 179.98(11) . . . . ?
C22 C21 C25 C26 -144.49(13) . . . . ?
C22 C21 C25 C30 35.91(18) . . . . ?
C23 O4 C19 O3 179.92(12) . . . . ?
C23 O4 C19 C20 0.30(17) . . . . ?
C23 N4 N5 N6 177.04(11) . . . . ?
C23 N4 N5 C24 1.54(14) . . . . ?
C23 C22 C24 N5 0.98(14) . . . . ?
C24 N5 N6 C31 113.90(14) . . . . ?
C24 N5 N6 C34 -115.54(14) . . . . ?
C24 C22 C23 O4 178.53(12) . . . . ?
C24 C22 C23 N4 -0.06(15) . . . . ?
C25 C21 C22 C23 176.75(12) . . . . ?
C25 C21 C22 C24 1.5(2) . . . . ?
C25 C26 C27 C28 -0.7(2) . . . . ?
C26 C25 C30 C29 0.38(19) . . . . ?
C26 C27 C28 C29 1.1(2) . . . . ?
C27 C28 C29 C30 -0.7(2) . . . . ?
C28 C29 C30 C25 0.0(2) . . . . ?
C30 C25 C26 C27 0.0(2) . . . . ?
C31 N6 C34 C35 -176.63(12) . . . . ?
C31 N6 C34 C36 56.62(16) . . . . ?
C34 N6 C31 C32 172.50(12) . . . . ?
C34 N6 C31 C33 51.68(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.730
_oxdiff_exptl_absorpt_empirical_full_min 0.291
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               3
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.5832(16) 16428 9455 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.3779(13) 0 8466 nmt -0.9998 0.0002 0.0003 -0.0046 -0.9999 -0.0009 0.7258
-0.0002 1.0000
3 0.0389(9) 0 1818 nmt -0.9946 -0.0118 0.0134 0.2514 0.9409 0.8938 -0.0077
0.1312 -0.9466

_twin_special_details            
;
Component 2 rotated by -179.9244° 
around [0.00 -0.00 1.00] (reciprocal) or [0.34 -0.00 0.94] (direct)
Component 3 rotated by 178.8065° 
around [-0.01 1.00 0.07] (reciprocal) or [0.11 0.90 0.42] (direct)
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_jft-r292_twin_hklf5
_database_code_depnum_ccdc_archive 'CCDC 2075643'
loop_
_audit_author_name
_audit_author_address
'Farzaneh Fadaei Tirani'
;EPFL ISIC
Switzerland
;
_audit_update_record             
;
2021-04-06 deposited with the CCDC.	2021-06-04 downloaded from the CCDC.
;
_audit_creation_date             2020-11-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H10 Cl F O2'
_chemical_formula_sum            'C17 H10 Cl F O2'
_chemical_formula_weight         300.70
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C17 H10 Cl F O2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   5.82517(17)
_cell_length_b                   19.3273(5)
_cell_length_c                   11.7017(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.745(3)
_cell_angle_gamma                90
_cell_volume                     1315.92(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10067
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      72.6510
_cell_measurement_theta_min      4.4090
_shelx_estimated_absorpt_T_max   0.879
_shelx_estimated_absorpt_T_min   0.442
_exptl_absorpt_coefficient_mu    2.700
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.405
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.41.89a (Rigaku Oxford Diffraction, 2020)
 Numerical absorption correction based on Gaussian integration over
 a multifaceted crystal model.
 Empirical absorption correction using spherical harmonics
 as implemented in SCALE3 ABSPACK scaling algorithm
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             616
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 2 1 0.0369
0 -2 -1 0.0274
-1 0 0 0.2039
1 0 0 0.1533
2 -2 -1 0.1424
0 -2 1 0.0114
0 2 -1 0.0380
-1 -2 -2 0.1328
0 -1 -2 0.0312

_exptl_crystal_size_max          0.361
_exptl_crystal_size_mid          0.069
_exptl_crystal_size_min          0.049
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0013 2.1919 0.8397 0.0362 0.1097 -0.1716
0.0013 -2.1919 -0.8397 -0.0362 -0.1097 0.1716
-0.9999 -0.0362 0.0068 0.1405 0.1690 0.1475
0.9999 0.0362 -0.0068 -0.1405 -0.1690 -0.1475
2.0010 -2.1195 -0.8532 -0.3171 -0.4478 -0.1234
0.0034 -1.7761 1.1447 0.1569 -0.1347 -0.0062
-0.0034 1.7761 -1.1447 -0.1569 0.1347 0.0062
-0.9995 -2.4360 -1.8251 0.0077 0.0718 0.4079
-0.0009 -1.4078 -1.9082 -0.1629 -0.0361 0.2191

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3810
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.602
_diffrn_reflns_theta_min         4.421
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2817
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -95.00 -59.00   1.00    2.00    --  -40.66 -71.00  45.00   36
  2  ω    -38.00 -11.00   1.00    2.00    --  -40.66 -71.00  45.00   27
  3  ω     10.00  69.00   1.00    2.00    --   40.66  71.00 176.00   59
  4  ω    113.00 140.00   1.00    8.00    --  105.15  71.00 176.00   27
  5  ω     76.00 103.00   1.00    8.00    --  105.15  71.00 176.00   27
  6  ω     53.00 121.00   1.00    8.00    --  105.15 -71.00  45.00   68
  7  ω     -3.00  22.00   1.00    2.00    --   34.00  89.00  67.48   25
  8  ω      2.00  27.00   1.00    2.00    --   38.00  88.00 -47.06   25
  9  ω   -114.00 -16.00   1.00    2.00    --  -40.66 -38.00  60.00   98
 10  ω    -70.00  32.00   1.00    2.00    --  -40.66  71.00 176.00  102
 11  ω    -18.00  56.00   1.00    2.00    --   40.66 -71.00  45.00   74
 12  ω     27.00  95.00   1.00    2.00    --   40.66-125.00 -30.00   68
 13  ω     84.00 115.00   1.00    2.00    --   40.66  71.00 176.00   31
 14  ω     13.00  38.00   1.00    2.00    --   46.00  82.00 138.73   25
 15  ω     16.00  41.00   1.00    2.00    --   50.00  82.00  -7.66   25
 16  ω     16.00  41.00   1.00    2.00    --   50.00  81.00  82.71   25
 17  ω     16.00  41.00   1.00    2.00    --   50.00  82.00 -74.34   25
 18  ω     16.00  42.00   1.00    2.00    --   50.00  81.00-178.86   26
 19  ω     26.00  58.00   1.00    2.00    --   58.00  73.00-123.00   32
 20  ω     34.00  64.00   1.00    2.00    --   58.00  71.00 113.05   30
 21  ω     98.00 132.00   1.00    2.00    --   58.00  71.00 113.05   34
 22  ω     39.00 110.00   1.00    2.00    --   66.00  73.00  25.16   71
 23  ω    102.00 127.00   1.00    2.00    --   66.00  72.00  80.97   25
 24  ω     38.00 101.00   1.00    2.00    --   66.00  73.00 -53.00   63
 25  ω     35.00  75.00   1.00    2.00    --   66.00  72.00  80.97   40
 26  ω     38.00 101.00   1.00    2.00    --   70.00  73.00 -83.24   63
 27  ω     38.00  65.00   1.00    2.00    --   70.00  74.00 157.79   27
 28  ω     39.00  73.00   1.00    2.00    --   70.00  73.00  -7.86   34
 29  ω     48.00  93.00   1.00    8.00    --   78.00  69.00-133.62   45
 30  ω     50.00  76.00   1.00    8.00    --   82.00  74.00-164.53   26
 31  ω     52.00  78.00   1.00    8.00    --   82.00  64.00 172.68   26
 32  ω     59.00  85.00   1.00    8.00    --   86.00  52.00 141.36   26
 33  ω     76.00 174.00   1.00    8.00    --  105.15  61.00 -90.00   98
 34  ω     99.00 136.00   1.00    8.00    --  105.15 178.00  60.00   37
 35  ω     76.00 177.00   1.00    8.00    --  105.15  61.00  90.00  101
 36  ω     76.00 106.00   1.00    8.00    --  105.15  61.00  60.00   30
 37  ω     63.00  92.00   1.00    8.00    --  105.15 178.00  60.00   29
 38  ω    120.00 177.00   1.00    8.00    --  105.15  61.00 -60.00   57
 39  ω     29.00 109.00   1.00    8.00    --  105.15-111.00  60.00   80
 40  ω     76.00 104.00   1.00    8.00    --  105.15  61.00 -60.00   28
 41  ω     31.00 109.00   1.00    8.00    --  105.15-111.00-150.00   78
 42  ω     77.00 175.00   1.00    8.00    --  105.15  61.00-150.00   98
 43  ω    121.00 157.00   1.00    8.00    --  105.15  61.00  30.00   36
 44  ω     79.00 119.00   1.00    8.00    --  105.15  61.00 120.00   40
 45  ω     77.00 104.00   1.00    8.00    --  105.15  61.00  30.00   27
 46  ω     64.00 146.00   1.00    8.00    --  105.15 178.00  90.00   82
 47  ω     79.00 162.00   1.00    8.00    --  105.15  61.00 150.00   83
 48  ω    128.00 176.00   1.00    8.00    --  105.15  61.00-120.00   48
 49  ω     76.00 103.00   1.00    8.00    --  105.15  61.00-120.00   27
 50  ω     76.00 145.00   1.00    8.00    --  105.15  61.00 -30.00   69
 51  ω     76.00 165.00   1.00    8.00    --  105.15  61.00   0.00   89
 52  ω     69.00 108.00   1.00    8.00    --  105.15-111.00 -90.00   39
 53  ω    118.00 147.00   1.00    8.00    --  105.15  61.00  60.00   29
 54  ω     34.00 117.00   1.00    8.00    --  105.15 -45.00-180.00   83
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1389651000
_diffrn_orient_matrix_UB_12      -0.0227323000
_diffrn_orient_matrix_UB_13      0.1022243000
_diffrn_orient_matrix_UB_21      -0.1713934000
_diffrn_orient_matrix_UB_22      0.0594857000
_diffrn_orient_matrix_UB_23      -0.0248949000
_diffrn_orient_matrix_UB_31      -0.1463021000
_diffrn_orient_matrix_UB_32      -0.0479447000
_diffrn_orient_matrix_UB_33      -0.0793946000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3335
_reflns_number_total             3810
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT 2018/2 (Sheldrick, 2015)'
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3810
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0333
_refine_ls_restrained_S_all      1.043
_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)+(0.0578P)²+0.1151P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0903
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.4948(15)
 0.5052(15)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.27754(7) 0.55485(2) 0.66220(4) 0.03238(14) Uani 1 1 d . . . . .
F1 F 0.4977(2) 0.93200(5) 0.42766(10) 0.0342(3) Uani 1 1 d . . . . .
O1 O 0.3335(2) 0.85114(6) 0.32310(11) 0.0278(3) Uani 1 1 d . . . . .
O2 O 0.1408(2) 0.77326(7) 0.21765(12) 0.0316(3) Uani 1 1 d . . . . .
C1 C 0.3051(3) 0.78285(9) 0.28120(15) 0.0243(4) Uani 1 1 d . . . . .
C2 C 0.5013(3) 0.86515(9) 0.40076(15) 0.0264(4) Uani 1 1 d . . . . .
C3 C 0.6501(3) 0.82012(9) 0.44727(15) 0.0249(4) Uani 1 1 d . . . . .
H3 H 0.759835 0.833519 0.505789 0.030 Uiso 1 1 calc R U . . .
C4 C 0.6385(3) 0.74983(8) 0.40524(14) 0.0211(3) Uani 1 1 d . . . . .
C5 C 0.4773(3) 0.73247(9) 0.32085(14) 0.0219(3) Uani 1 1 d . . . . .
C6 C 0.8012(3) 0.69971(8) 0.46163(14) 0.0198(3) Uani 1 1 d . . . . .
C7 C 0.7373(3) 0.63132(9) 0.48224(14) 0.0222(3) Uani 1 1 d . . . . .
H7 H 0.591221 0.615247 0.453997 0.027 Uiso 1 1 calc R U . . .
C8 C 0.8831(3) 0.58649(9) 0.54316(15) 0.0239(3) Uani 1 1 d . . . . .
H8 H 0.837782 0.540133 0.556985 0.029 Uiso 1 1 calc R U . . .
C9 C 1.0966(3) 0.61054(9) 0.58364(14) 0.0230(3) Uani 1 1 d . . . . .
C10 C 1.1660(3) 0.67800(9) 0.56520(14) 0.0231(3) Uani 1 1 d . . . . .
H10 H 1.312299 0.693756 0.593670 0.028 Uiso 1 1 calc R U . . .
C11 C 1.0173(3) 0.72211(9) 0.50422(14) 0.0217(3) Uani 1 1 d . . . . .
H11 H 1.063119 0.768493 0.491112 0.026 Uiso 1 1 calc R U . . .
C12 C 0.4618(3) 0.66439(9) 0.26200(14) 0.0219(3) Uani 1 1 d . . . . .
C13 C 0.2676(3) 0.62243(10) 0.26874(15) 0.0252(4) Uani 1 1 d . . . . .
H13 H 0.142565 0.637531 0.311660 0.030 Uiso 1 1 calc R U . . .
C14 C 0.2553(3) 0.55913(9) 0.21359(16) 0.0278(4) Uani 1 1 d . . . . .
H14 H 0.123433 0.530724 0.219831 0.033 Uiso 1 1 calc R U . . .
C15 C 0.4350(3) 0.53709(9) 0.14928(15) 0.0283(4) Uani 1 1 d . . . . .
H15 H 0.426030 0.493798 0.110893 0.034 Uiso 1 1 calc R U . . .
C16 C 0.6286(3) 0.57858(9) 0.14113(15) 0.0267(4) Uani 1 1 d . . . . .
H16 H 0.751837 0.563562 0.096965 0.032 Uiso 1 1 calc R U . . .
C17 C 0.6425(3) 0.64176(9) 0.19714(15) 0.0234(3) Uani 1 1 d . . . . .
H17 H 0.775505 0.669777 0.191395 0.028 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C9 1.7383(16) . ?
F1 C2 1.330(2) . ?
O1 C1 1.415(2) . ?
O1 C2 1.330(2) . ?
O2 C1 1.198(2) . ?
C1 C5 1.458(2) . ?
C2 C3 1.327(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.445(2) . ?
C4 C5 1.371(2) . ?
C4 C6 1.488(2) . ?
C5 C12 1.486(2) . ?
C6 C7 1.397(2) . ?
C6 C11 1.400(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.386(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.390(2) . ?
C9 C10 1.385(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.388(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.397(2) . ?
C12 C17 1.397(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.383(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.385(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.391(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.386(3) . ?
C17 H17 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C1 119.77(13) . . ?
O1 C1 C5 116.45(15) . . ?
O2 C1 O1 115.86(15) . . ?
O2 C1 C5 127.68(17) . . ?
F1 C2 O1 109.88(14) . . ?
C3 C2 F1 123.87(17) . . ?
C3 C2 O1 126.24(17) . . ?
C2 C3 H3 121.4 . . ?
C2 C3 C4 117.25(16) . . ?
C4 C3 H3 121.4 . . ?
C3 C4 C6 116.27(15) . . ?
C5 C4 C3 119.64(15) . . ?
C5 C4 C6 124.05(15) . . ?
C1 C5 C12 114.74(15) . . ?
C4 C5 C1 120.18(16) . . ?
C4 C5 C12 125.08(14) . . ?
C7 C6 C4 121.54(14) . . ?
C7 C6 C11 118.27(15) . . ?
C11 C6 C4 119.97(15) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 C6 121.20(15) . . ?
C8 C7 H7 119.4 . . ?
C7 C8 H8 120.6 . . ?
C7 C8 C9 118.85(16) . . ?
C9 C8 H8 120.6 . . ?
C8 C9 Cl1 118.89(13) . . ?
C10 C9 Cl1 119.42(13) . . ?
C10 C9 C8 121.67(15) . . ?
C9 C10 H10 120.7 . . ?
C9 C10 C11 118.58(16) . . ?
C11 C10 H10 120.7 . . ?
C6 C11 H11 119.3 . . ?
C10 C11 C6 121.43(16) . . ?
C10 C11 H11 119.3 . . ?
C13 C12 C5 121.27(15) . . ?
C17 C12 C5 119.89(15) . . ?
C17 C12 C13 118.84(16) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.70(16) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.14(16) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.75(17) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.32(16) . . ?
C17 C16 H16 119.8 . . ?
C12 C17 H17 119.9 . . ?
C16 C17 C12 120.24(16) . . ?
C16 C17 H17 119.9 . . ?

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
Cl1 C9 C10 C11 -178.73(13) . . . . ?
F1 C2 C3 C4 -177.27(15) . . . . ?
O1 C1 C5 C4 8.0(2) . . . . ?
O1 C1 C5 C12 -171.28(13) . . . . ?
O1 C2 C3 C4 3.8(3) . . . . ?
O2 C1 C5 C4 -171.53(17) . . . . ?
O2 C1 C5 C12 9.2(3) . . . . ?
C1 O1 C2 F1 179.70(13) . . . . ?
C1 O1 C2 C3 -1.3(2) . . . . ?
C1 C5 C12 C13 -62.5(2) . . . . ?
C1 C5 C12 C17 116.60(17) . . . . ?
C2 O1 C1 O2 174.94(15) . . . . ?
C2 O1 C1 C5 -4.6(2) . . . . ?
C2 C3 C4 C5 -0.2(2) . . . . ?
C2 C3 C4 C6 -177.82(15) . . . . ?
C3 C4 C5 C1 -5.7(2) . . . . ?
C3 C4 C5 C12 173.51(15) . . . . ?
C3 C4 C6 C7 142.64(16) . . . . ?
C3 C4 C6 C11 -31.9(2) . . . . ?
C4 C5 C12 C13 118.28(19) . . . . ?
C4 C5 C12 C17 -62.6(2) . . . . ?
C4 C6 C7 C8 -174.63(15) . . . . ?
C4 C6 C11 C10 174.86(15) . . . . ?
C5 C4 C6 C7 -34.9(2) . . . . ?
C5 C4 C6 C11 150.58(16) . . . . ?
C5 C12 C13 C14 -179.97(16) . . . . ?
C5 C12 C17 C16 -179.42(15) . . . . ?
C6 C4 C5 C1 171.80(15) . . . . ?
C6 C4 C5 C12 -9.0(3) . . . . ?
C6 C7 C8 C9 -0.3(2) . . . . ?
C7 C6 C11 C10 0.2(2) . . . . ?
C7 C8 C9 Cl1 178.87(13) . . . . ?
C7 C8 C9 C10 0.4(3) . . . . ?
C8 C9 C10 C11 -0.3(3) . . . . ?
C9 C10 C11 C6 0.0(2) . . . . ?
C11 C6 C7 C8 0.0(2) . . . . ?
C12 C13 C14 C15 -1.0(3) . . . . ?
C13 C12 C17 C16 -0.3(2) . . . . ?
C13 C14 C15 C16 0.5(3) . . . . ?
C14 C15 C16 C17 0.1(3) . . . . ?
C15 C16 C17 C12 -0.2(3) . . . . ?
C17 C12 C13 C14 0.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.778
_oxdiff_exptl_absorpt_empirical_full_min 0.539
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.4948(15) 16130 4153 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.5052(15) 0 4153 nmt -1.0001 -0.0014 -0.0011 -0.0360 0.9928 -0.2082 0.0067
-0.0763 -0.9919

_twin_special_details            
;
Component 2 rotated by -179.8479° 
around [-0.00 1.00 -0.04] (reciprocal) or [-0.02 0.99 -0.10] (direct)
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_jft-r352
_database_code_depnum_ccdc_archive 'CCDC 2075644'
loop_
_audit_author_name
_audit_author_address
'Farzaneh Fadaei Tirani'
;EPFL ISIC
Switzerland
;
_audit_update_record             
;
2021-04-06 deposited with the CCDC.	2021-06-04 downloaded from the CCDC.
;
_audit_creation_date             2020-12-10
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H25 N3 O2'
_chemical_formula_sum            'C20 H25 N3 O2'
_chemical_formula_weight         339.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H25 N3 O2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.4488(6)
_cell_length_b                   13.1778(8)
_cell_length_c                   15.6415(10)
_cell_angle_alpha                109.270(6)
_cell_angle_beta                 97.031(5)
_cell_angle_gamma                111.857(6)
_cell_volume                     1811.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3996
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      71.6530
_cell_measurement_theta_min      3.0840
_shelx_estimated_absorpt_T_max   0.925
_shelx_estimated_absorpt_T_min   0.862
_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.664
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             728
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 -1 0.0903
-1 0 1 0.1133
5 3 -3 0.1021
-3 3 5 0.1060
3 -3 -5 0.0827
2 -5 0 0.0752
-2 5 0 0.1006
-5 5 3 0.0951
5 -5 -3 0.0730
-3 -5 5 0.1224
0 -5 2 0.0990
-2 5 -2 0.0892
-1 1 -1 0.0518
0 3 -5 0.0891
-5 3 -5 0.0536
0 -3 5 0.0883
2 1 2 0.0689
0 3 5 0.0746
2 0 -5 0.0894
0 0 -1 0.0810
-5 0 -3 0.0705
0 -5 -3 0.0919
2 -5 -5 0.0807
3 -5 1 0.0679
3 -5 4 0.0518
5 -2 -1 0.0785
-2 -1 5 0.0990

_exptl_crystal_size_max          0.236
_exptl_crystal_size_mid          0.174
_exptl_crystal_size_min          0.122
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0004 -0.0001 -0.9995 -0.0083 -0.0042 -0.1704
-1.0004 0.0001 0.9995 0.0083 0.0042 0.1704
4.9999 3.0035 -2.9999 0.4903 -0.1153 -0.8658
-3.0035 3.0041 4.9958 0.5569 -0.0817 0.4977
3.0035 -3.0041 -4.9958 -0.5569 0.0817 -0.4977
2.0041 -5.0064 0.0034 -0.5505 -0.2628 -0.1135
-2.0041 5.0064 -0.0034 0.5505 0.2628 0.1135
-5.0053 5.0067 2.9950 0.5755 0.2755 0.6248
5.0053 -5.0067 -2.9950 -0.5755 -0.2755 -0.6248
-2.9980 -5.0060 5.0007 -0.5089 -0.2418 0.7387
0.0032 -5.0063 2.0023 -0.5339 -0.2544 0.2274
-2.0039 5.0064 -2.0026 0.4183 0.4172 0.0367
-1.0009 1.0013 -1.0004 0.0093 0.1786 0.0635
-0.0016 3.0037 -4.9999 0.0691 0.4460 -0.2823
-5.0033 3.0039 -5.0007 -0.2199 0.8529 0.3779
0.0016 -3.0037 4.9999 -0.0691 -0.4460 0.2823
1.9998 1.0012 1.9989 0.3811 -0.2971 -0.2174
-0.0025 3.0039 4.9962 0.7303 -0.3259 0.1016
2.0011 -0.0002 -4.9978 -0.2150 0.2231 -0.4560
0.0001 -0.0000 -0.9996 -0.0661 0.0772 -0.0384
-5.0015 0.0002 -2.9997 -0.4874 0.6385 0.5451
0.0036 -5.0064 -2.9958 -0.8645 0.1315 0.0354
2.0045 -5.0066 -4.9947 -0.8811 0.1231 -0.3054
3.0043 -5.0065 1.0032 -0.4266 -0.4214 -0.2071
3.0041 -5.0064 4.0020 -0.2282 -0.6530 -0.0920
5.0031 -2.0028 -0.9976 -0.0436 -0.3698 -0.6384
-2.0004 -1.0010 4.9984 0.0818 -0.2432 0.4862

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_unetI/netI     0.0548
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15128
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.679
_diffrn_reflns_theta_min         3.118
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2665
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00 -15.00   1.00    1.50    --  -43.01  95.00-174.00   45
  2  ω     23.00  69.00   1.00    1.50    --   43.01 -95.00  75.00   46
  3  ω     60.00 106.00   1.00    6.00    --  103.80 -95.00  75.00   46
  4  ω    104.00 171.00   1.00    6.00    --  103.80  95.00-174.00   67
  5  ω   -105.00 -17.00   1.00    1.50    --  -43.01 -57.00-120.00   88
  6  ω    -79.00  -8.00   1.00    1.50    --  -43.01 125.00  60.00   71
  7  ω   -112.00 -20.00   1.00    1.50    --  -43.01 -57.00   0.00   92
  8  ω     19.00 100.00   1.00    1.50    --   43.01  37.00   0.00   81
  9  ω     76.00 168.00   1.00    6.00    --  103.80  30.00-180.00   92
 10  ω     30.00  57.00   1.00    6.00    --  103.80-111.00-120.00   27
 11  ω    103.00 176.00   1.00    6.00    --  103.80  77.00-120.00   73
 12  ω     29.00 108.00   1.00    6.00    --  103.80-111.00 -30.00   79
 13  ω     37.00 106.00   1.00    6.00    --  103.80-111.00  60.00   69
 14  ω     76.00 103.00   1.00    6.00    --  103.80  30.00 120.00   27
 15  ω    116.00 176.00   1.00    6.00    --  103.80  30.00 120.00   60
 16  ω    141.00 166.00   1.00    6.00    --  103.80 111.00-120.00   25
 17  ω     42.00  95.00   1.00    6.00    --  103.80-111.00-180.00   53
 18  ω     67.00 108.00   1.00    6.00    --  103.80-111.00-120.00   41
 19  ω     73.00 124.00   1.00    6.00    --  103.80 178.00  90.00   51
 20  ω     55.00 130.00   1.00    6.00    --  103.80 -45.00 120.00   75
 21  ω    108.00 168.00   1.00    6.00    --  103.80 111.00  30.00   60
 22  ω    129.00 178.00   1.00    6.00    --  103.80  77.00  90.00   49
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0577797000
_diffrn_orient_matrix_UB_12      0.1331357000
_diffrn_orient_matrix_UB_13      0.0661456000
_diffrn_orient_matrix_UB_21      -0.0813410000
_diffrn_orient_matrix_UB_22      0.0198889000
_diffrn_orient_matrix_UB_23      -0.0772177000
_diffrn_orient_matrix_UB_31      -0.1320102000
_diffrn_orient_matrix_UB_32      -0.0301497000
_diffrn_orient_matrix_UB_33      0.0383940000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5303
_reflns_number_total             7000
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     648
_refine_ls_number_reflns         7000
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0859
_refine_ls_R_factor_gt           0.0654
_refine_ls_restrained_S_all      1.092
_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)+(0.0917P)²+0.5831P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1676
_refine_ls_wR_factor_ref         0.1839
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.1812(2) 0.84471(18) 0.28406(15) 0.0378(5) Uani 1 1 d . . . . .
O2 O 1.05477(17) 0.72483(15) 0.34475(12) 0.0282(4) Uani 1 1 d . . . . .
N1 N 0.9192(2) 0.60890(19) 0.41444(15) 0.0282(4) Uani 1 1 d . . . . .
N2 N 0.8031(2) 0.60804(19) 0.44843(15) 0.0271(4) Uani 1 1 d . . . . .
N3 N 0.7418(2) 0.52985(18) 0.49060(15) 0.0265(4) Uani 1 1 d . . . . .
C1 C 1.0805(3) 0.8186(2) 0.31622(18) 0.0295(5) Uani 1 1 d . . . . .
C2 C 0.9829(3) 0.8741(2) 0.32612(18) 0.0296(5) Uani 1 1 d . . . . .
H2 H 1.006(3) 0.938(3) 0.304(2) 0.022(6) Uiso 1 1 d . . . . .
C3 C 0.8698(2) 0.8408(2) 0.36182(17) 0.0258(5) Uani 1 1 d . . . . .
C4 C 0.8490(2) 0.7467(2) 0.39366(17) 0.0254(5) Uani 1 1 d . . . . .
C5 C 0.9439(2) 0.6932(2) 0.38303(17) 0.0251(5) Uani 1 1 d . . . . .
C6 C 0.7713(3) 0.8986(2) 0.36751(17) 0.0271(5) Uani 1 1 d . . . . .
C7 C 0.8255(3) 1.0229(2) 0.4151(2) 0.0338(5) Uani 1 1 d . . . . .
H7 H 0.921(4) 1.070(3) 0.442(2) 0.041 Uiso 1 1 d . U . . .
C8 C 0.7324(4) 1.0754(3) 0.4253(2) 0.0437(7) Uani 1 1 d . . . . .
H8 H 0.774(4) 1.164(4) 0.458(3) 0.060(11) Uiso 1 1 d . . . . .
C9 C 0.5859(4) 1.0060(3) 0.3875(2) 0.0458(7) Uani 1 1 d . . . . .
H9 H 0.521(4) 1.042(4) 0.395(3) 0.061(11) Uiso 1 1 d . . . . .
C10 C 0.5306(3) 0.8830(3) 0.3382(2) 0.0394(6) Uani 1 1 d . . . . .
H10 H 0.435(4) 0.840(3) 0.312(2) 0.035(8) Uiso 1 1 d . . . . .
C11 C 0.6234(3) 0.8293(2) 0.32819(19) 0.0314(5) Uani 1 1 d . . . . .
H11 H 0.584(3) 0.741(3) 0.292(2) 0.032(7) Uiso 1 1 d . . . . .
C12 C 0.7595(2) 0.6895(2) 0.43951(17) 0.0261(5) Uani 1 1 d . . . . .
C13 C 0.6431(3) 0.7085(2) 0.4794(2) 0.0310(5) Uani 1 1 d . . . . .
H13A H 0.611(3) 0.648(3) 0.502(2) 0.032(7) Uiso 1 1 d . . . . .
H13B H 0.575(3) 0.703(3) 0.434(2) 0.024(7) Uiso 1 1 d . . . . .
C14 C 0.6980(3) 0.8302(3) 0.5617(2) 0.0408(7) Uani 1 1 d . . . . .
H14A H 0.742(4) 0.892(3) 0.545(2) 0.041(9) Uiso 1 1 d . . . . .
H14B H 0.620(4) 0.847(4) 0.586(3) 0.061(11) Uiso 1 1 d . . . . .
H14C H 0.778(5) 0.837(4) 0.615(3) 0.067(12) Uiso 1 1 d . . . . .
C15 C 0.8534(3) 0.5459(2) 0.56906(19) 0.0318(5) Uani 1 1 d . . . . .
H15 H 0.933(3) 0.530(3) 0.543(2) 0.030(7) Uiso 1 1 d . . . . .
C16 C 0.9183(3) 0.6737(3) 0.6422(2) 0.0408(6) Uani 1 1 d . . . . .
H16A H 0.986(4) 0.683(3) 0.689(3) 0.037(8) Uiso 1 1 d . . . . .
H16B H 0.843(3) 0.693(3) 0.668(2) 0.035(8) Uiso 1 1 d . . . . .
H16C H 0.967(4) 0.734(3) 0.617(3) 0.045(9) Uiso 1 1 d . . . . .
C17 C 0.7887(3) 0.4593(3) 0.6132(2) 0.0395(6) Uani 1 1 d . . . . .
H17A H 0.755(4) 0.376(4) 0.577(3) 0.050(10) Uiso 1 1 d . . . . .
H17B H 0.865(4) 0.480(3) 0.667(3) 0.041(8) Uiso 1 1 d . . . . .
H17C H 0.706(4) 0.475(4) 0.633(3) 0.061(11) Uiso 1 1 d . . . . .
C18 C 0.6530(3) 0.4054(2) 0.41887(18) 0.0296(5) Uani 1 1 d . . . . .
H18 H 0.605(3) 0.359(3) 0.455(2) 0.032(8) Uiso 1 1 d . . . . .
C19 C 0.5361(3) 0.4019(3) 0.3488(2) 0.0393(6) Uani 1 1 d . . . . .
H19A H 0.474(4) 0.320(4) 0.307(3) 0.047(9) Uiso 1 1 d . . . . .
H19B H 0.480(4) 0.436(4) 0.376(3) 0.054(10) Uiso 1 1 d . . . . .
H19C H 0.573(4) 0.444(4) 0.310(3) 0.053(10) Uiso 1 1 d . . . . .
C20 C 0.7354(3) 0.3416(3) 0.3691(2) 0.0398(7) Uani 1 1 d . . . . .
H20A H 0.777(4) 0.377(3) 0.326(3) 0.048(9) Uiso 1 1 d . . . . .
H20B H 0.818(4) 0.342(3) 0.415(3) 0.050(10) Uiso 1 1 d . . . . .
H20C H 0.662(5) 0.252(4) 0.329(3) 0.070(12) Uiso 1 1 d . . . . .
O3 O 1.35269(18) 0.56739(17) 0.19687(15) 0.0371(4) Uani 1 1 d . . . . .
O4 O 1.17935(17) 0.38430(15) 0.14724(13) 0.0282(4) Uani 1 1 d . . . . .
N4 N 0.9891(2) 0.19446(18) 0.08330(15) 0.0269(4) Uani 1 1 d . . . . .
N5 N 0.8432(2) 0.15413(18) 0.04891(15) 0.0254(4) Uani 1 1 d . . . . .
N6 N 0.7483(2) 0.03239(17) 0.01277(14) 0.0252(4) Uani 1 1 d . . . . .
C21 C 1.2250(3) 0.5059(2) 0.16815(18) 0.0283(5) Uani 1 1 d . . . . .
C22 C 1.1156(3) 0.5480(2) 0.15835(18) 0.0283(5) Uani 1 1 d . . . . .
H22 H 1.150(3) 0.637(3) 0.179(2) 0.034 Uiso 1 1 d . U . . .
C23 C 0.9723(3) 0.4752(2) 0.12615(17) 0.0258(5) Uani 1 1 d . . . . .
C24 C 0.9291(2) 0.3489(2) 0.09801(17) 0.0257(5) Uani 1 1 d . . . . .
C25 C 1.0364(2) 0.3105(2) 0.11089(17) 0.0255(5) Uani 1 1 d . . . . .
C26 C 0.8662(3) 0.5241(2) 0.12129(17) 0.0269(5) Uani 1 1 d . . . . .
C27 C 0.8823(3) 0.6069(2) 0.08107(19) 0.0325(5) Uani 1 1 d . . . . .
H27 H 0.963(3) 0.632(3) 0.057(2) 0.032(7) Uiso 1 1 d . . . . .
C28 C 0.7804(4) 0.6496(3) 0.0734(2) 0.0413(7) Uani 1 1 d . . . . .
H28 H 0.789(4) 0.702(4) 0.039(3) 0.056(10) Uiso 1 1 d . . . . .
C29 C 0.6620(3) 0.6117(3) 0.1071(2) 0.0425(7) Uani 1 1 d . . . . .
H29 H 0.582(4) 0.640(4) 0.096(3) 0.058(11) Uiso 1 1 d . . . . .
C30 C 0.6471(3) 0.5326(3) 0.1496(2) 0.0387(6) Uani 1 1 d . . . . .
H30 H 0.566(5) 0.507(4) 0.172(3) 0.068(12) Uiso 1 1 d . . . . .
C31 C 0.7483(3) 0.4890(2) 0.15656(19) 0.0316(5) Uani 1 1 d . . . . .
H31 H 0.739(3) 0.437(3) 0.184(2) 0.035(8) Uiso 1 1 d . . . . .
C32 C 0.8022(2) 0.2420(2) 0.05392(17) 0.0254(5) Uani 1 1 d . . . . .
C33 C 0.6512(3) 0.2133(2) 0.00947(19) 0.0290(5) Uani 1 1 d . . . . .
H33A H 0.593(3) 0.125(3) -0.010(2) 0.025(7) Uiso 1 1 d . . . . .
H33B H 0.613(3) 0.254(3) 0.057(2) 0.037(8) Uiso 1 1 d . . . . .
C34 C 0.6386(3) 0.2492(3) -0.0738(2) 0.0363(6) Uani 1 1 d . . . . .
H34A H 0.538(4) 0.219(3) -0.106(2) 0.040(8) Uiso 1 1 d . . . . .
H34B H 0.689(4) 0.333(3) -0.056(2) 0.042(9) Uiso 1 1 d . . . . .
H34C H 0.687(4) 0.213(4) -0.117(3) 0.057(11) Uiso 1 1 d . . . . .
C35 C 0.7307(3) -0.0104(2) 0.08985(18) 0.0278(5) Uani 1 1 d . . . . .
H35 H 0.650(3) -0.092(3) 0.058(2) 0.035(8) Uiso 1 1 d . . . . .
C36 C 0.6809(3) 0.0655(3) 0.1619(2) 0.0361(6) Uani 1 1 d . . . . .
H36A H 0.659(3) 0.028(3) 0.204(2) 0.032(7) Uiso 1 1 d . . . . .
H36B H 0.599(4) 0.071(3) 0.134(3) 0.045(9) Uiso 1 1 d . . . . .
H36C H 0.763(4) 0.146(3) 0.198(2) 0.040(8) Uiso 1 1 d . . . . .
C37 C 0.8592(3) -0.0199(3) 0.1380(2) 0.0362(6) Uani 1 1 d . . . . .
H37A H 0.936(4) 0.056(3) 0.183(3) 0.046(9) Uiso 1 1 d . . . . .
H37B H 0.889(3) -0.071(3) 0.084(2) 0.038(8) Uiso 1 1 d . . . . .
H37C H 0.819(4) -0.065(4) 0.182(3) 0.055(10) Uiso 1 1 d . . . . .
C38 C 0.7892(3) -0.0375(2) -0.06611(18) 0.0296(5) Uani 1 1 d . . . . .
H38 H 0.887(3) -0.023(3) -0.040(2) 0.023(7) Uiso 1 1 d . . . . .
C39 C 0.7854(3) 0.0091(3) -0.1429(2) 0.0393(6) Uani 1 1 d . . . . .
H39A H 0.681(4) 0.002(3) -0.168(3) 0.047 Uiso 1 1 d . U . . .
H39B H 0.805(4) -0.038(3) -0.196(3) 0.046(9) Uiso 1 1 d . . . . .
H39C H 0.859(4) 0.096(4) -0.117(3) 0.048(9) Uiso 1 1 d . . . . .
C40 C 0.6856(3) -0.1695(3) -0.1055(2) 0.0380(6) Uani 1 1 d . . . . .
H40A H 0.592(4) -0.179(3) -0.126(2) 0.039(8) Uiso 1 1 d . . . . .
H40B H 0.687(4) -0.205(3) -0.059(3) 0.047(9) Uiso 1 1 d . . . . .
H40C H 0.717(4) -0.210(3) -0.158(3) 0.050(10) Uiso 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
O1 C1 1.206(3) . ?
O2 C1 1.394(3) . ?
O2 C5 1.360(3) . ?
N1 N2 1.381(3) . ?
N1 C5 1.311(3) . ?
N2 N3 1.403(3) . ?
N2 C12 1.352(3) . ?
N3 C15 1.485(3) . ?
N3 C18 1.485(3) . ?
C1 C2 1.455(4) . ?
C2 C3 1.356(3) . ?
C3 C4 1.438(3) . ?
C3 C6 1.486(3) . ?
C4 C5 1.412(3) . ?
C4 C12 1.397(3) . ?
C6 C7 1.400(4) . ?
C6 C11 1.395(4) . ?
C7 C8 1.385(4) . ?
C8 C9 1.381(5) . ?
C9 C10 1.387(5) . ?
C10 C11 1.394(4) . ?
C12 C13 1.496(3) . ?
C13 C14 1.527(4) . ?
C15 C16 1.514(4) . ?
C15 C17 1.516(4) . ?
C18 C19 1.514(4) . ?
C18 C20 1.525(4) . ?
O3 C21 1.203(3) . ?
O4 C21 1.396(3) . ?
O4 C25 1.359(3) . ?
N4 N5 1.379(3) . ?
N4 C25 1.311(3) . ?
N5 N6 1.399(3) . ?
N5 C32 1.359(3) . ?
N6 C35 1.493(3) . ?
N6 C38 1.491(3) . ?
C21 C22 1.457(4) . ?
C22 C23 1.358(3) . ?
C23 C24 1.441(3) . ?
C23 C26 1.482(3) . ?
C24 C25 1.409(3) . ?
C24 C32 1.401(3) . ?
C26 C27 1.398(4) . ?
C26 C31 1.395(3) . ?
C27 C28 1.387(4) . ?
C28 C29 1.390(5) . ?
C29 C30 1.385(5) . ?
C30 C31 1.387(4) . ?
C32 C33 1.494(3) . ?
C33 C34 1.531(4) . ?
C35 C36 1.525(4) . ?
C35 C37 1.526(4) . ?
C38 C39 1.521(4) . ?
C38 C40 1.518(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
C5 O2 C1 118.61(19) . . ?
C5 N1 N2 101.81(19) . . ?
N1 N2 N3 120.87(19) . . ?
C12 N2 N1 114.34(19) . . ?
C12 N2 N3 124.76(18) . . ?
N2 N3 C15 110.09(19) . . ?
N2 N3 C18 111.37(19) . . ?
C15 N3 C18 116.4(2) . . ?
O1 C1 O2 116.3(2) . . ?
O1 C1 C2 126.1(2) . . ?
O2 C1 C2 117.6(2) . . ?
C3 C2 C1 124.1(2) . . ?
C2 C3 C4 117.0(2) . . ?
C2 C3 C6 121.6(2) . . ?
C4 C3 C6 121.4(2) . . ?
C5 C4 C3 118.2(2) . . ?
C12 C4 C3 138.1(2) . . ?
C12 C4 C5 103.6(2) . . ?
O2 C5 C4 124.4(2) . . ?
N1 C5 O2 120.8(2) . . ?
N1 C5 C4 114.8(2) . . ?
C7 C6 C3 120.3(2) . . ?
C11 C6 C3 120.4(2) . . ?
C11 C6 C7 119.3(2) . . ?
C8 C7 C6 120.0(3) . . ?
C9 C8 C7 120.4(3) . . ?
C8 C9 C10 120.3(3) . . ?
C9 C10 C11 119.7(3) . . ?
C10 C11 C6 120.3(3) . . ?
N2 C12 C4 105.4(2) . . ?
N2 C12 C13 121.9(2) . . ?
C4 C12 C13 132.6(2) . . ?
C12 C13 C14 112.9(2) . . ?
N3 C15 C16 109.2(2) . . ?
N3 C15 C17 110.3(2) . . ?
C16 C15 C17 110.3(2) . . ?
N3 C18 C19 110.2(2) . . ?
N3 C18 C20 115.8(2) . . ?
C19 C18 C20 111.5(2) . . ?
C25 O4 C21 118.13(19) . . ?
C25 N4 N5 101.89(19) . . ?
N4 N5 N6 121.46(19) . . ?
C32 N5 N4 114.37(19) . . ?
C32 N5 N6 124.17(19) . . ?
N5 N6 C35 111.15(19) . . ?
N5 N6 C38 110.25(17) . . ?
C38 N6 C35 115.94(19) . . ?
O3 C21 O4 116.1(2) . . ?
O3 C21 C22 125.9(2) . . ?
O4 C21 C22 117.9(2) . . ?
C23 C22 C21 123.9(2) . . ?
C22 C23 C24 116.8(2) . . ?
C22 C23 C26 121.3(2) . . ?
C24 C23 C26 122.0(2) . . ?
C25 C24 C23 118.4(2) . . ?
C32 C24 C23 137.8(2) . . ?
C32 C24 C25 103.7(2) . . ?
O4 C25 C24 124.6(2) . . ?
N4 C25 O4 120.4(2) . . ?
N4 C25 C24 114.9(2) . . ?
C27 C26 C23 120.5(2) . . ?
C31 C26 C23 121.0(2) . . ?
C31 C26 C27 118.5(2) . . ?
C28 C27 C26 120.6(2) . . ?
C27 C28 C29 120.1(3) . . ?
C30 C29 C28 119.8(3) . . ?
C29 C30 C31 120.1(3) . . ?
C30 C31 C26 120.8(3) . . ?
N5 C32 C24 105.0(2) . . ?
N5 C32 C33 121.4(2) . . ?
C24 C32 C33 133.3(2) . . ?
C32 C33 C34 112.5(2) . . ?
N6 C35 C36 109.6(2) . . ?
N6 C35 C37 116.44(19) . . ?
C36 C35 C37 111.1(2) . . ?
N6 C38 C39 108.7(2) . . ?
N6 C38 C40 110.1(2) . . ?
C40 C38 C39 110.0(2) . . ?

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
O1 C1 C2 C3 179.2(3) . . . . ?
O2 C1 C2 C3 0.5(4) . . . . ?
N1 N2 N3 C15 54.8(3) . . . . ?
N1 N2 N3 C18 -75.8(3) . . . . ?
N1 N2 C12 C4 2.0(3) . . . . ?
N1 N2 C12 C13 -175.0(2) . . . . ?
N2 N1 C5 O2 178.5(2) . . . . ?
N2 N1 C5 C4 -0.7(3) . . . . ?
N2 N3 C15 C16 60.2(2) . . . . ?
N2 N3 C15 C17 -178.5(2) . . . . ?
N2 N3 C18 C19 -57.8(2) . . . . ?
N2 N3 C18 C20 69.8(3) . . . . ?
N2 C12 C13 C14 111.8(3) . . . . ?
N3 N2 C12 C4 -179.8(2) . . . . ?
N3 N2 C12 C13 3.2(4) . . . . ?
C1 O2 C5 N1 -177.2(2) . . . . ?
C1 O2 C5 C4 2.0(4) . . . . ?
C1 C2 C3 C4 1.6(4) . . . . ?
C1 C2 C3 C6 -178.1(2) . . . . ?
C2 C3 C4 C5 -2.0(3) . . . . ?
C2 C3 C4 C12 174.4(3) . . . . ?
C2 C3 C6 C7 -55.7(3) . . . . ?
C2 C3 C6 C11 126.4(3) . . . . ?
C3 C4 C5 O2 0.2(4) . . . . ?
C3 C4 C5 N1 179.4(2) . . . . ?
C3 C4 C12 N2 -178.9(3) . . . . ?
C3 C4 C12 C13 -2.4(5) . . . . ?
C3 C6 C7 C8 -175.9(2) . . . . ?
C3 C6 C11 C10 176.4(2) . . . . ?
C4 C3 C6 C7 124.5(3) . . . . ?
C4 C3 C6 C11 -53.4(3) . . . . ?
C4 C12 C13 C14 -64.3(4) . . . . ?
C5 O2 C1 O1 178.9(2) . . . . ?
C5 O2 C1 C2 -2.2(3) . . . . ?
C5 N1 N2 N3 -179.1(2) . . . . ?
C5 N1 N2 C12 -0.9(3) . . . . ?
C5 C4 C12 N2 -2.2(3) . . . . ?
C5 C4 C12 C13 174.3(3) . . . . ?
C6 C3 C4 C5 177.8(2) . . . . ?
C6 C3 C4 C12 -5.8(5) . . . . ?
C6 C7 C8 C9 -1.0(4) . . . . ?
C7 C6 C11 C10 -1.5(4) . . . . ?
C7 C8 C9 C10 -0.5(5) . . . . ?
C8 C9 C10 C11 1.1(5) . . . . ?
C9 C10 C11 C6 0.0(4) . . . . ?
C11 C6 C7 C8 2.1(4) . . . . ?
C12 N2 N3 C15 -123.2(2) . . . . ?
C12 N2 N3 C18 106.2(3) . . . . ?
C12 C4 C5 O2 -177.3(2) . . . . ?
C12 C4 C5 N1 1.9(3) . . . . ?
C15 N3 C18 C19 174.9(2) . . . . ?
C15 N3 C18 C20 -57.5(3) . . . . ?
C18 N3 C15 C16 -171.90(19) . . . . ?
C18 N3 C15 C17 -50.5(3) . . . . ?
O3 C21 C22 C23 -179.5(3) . . . . ?
O4 C21 C22 C23 -3.0(4) . . . . ?
N4 N5 N6 C35 72.7(2) . . . . ?
N4 N5 N6 C38 -57.3(3) . . . . ?
N4 N5 C32 C24 -2.3(3) . . . . ?
N4 N5 C32 C33 172.5(2) . . . . ?
N5 N4 C25 O4 -177.9(2) . . . . ?
N5 N4 C25 C24 1.1(3) . . . . ?
N5 N6 C35 C36 56.3(3) . . . . ?
N5 N6 C35 C37 -70.9(3) . . . . ?
N5 N6 C38 C39 -59.1(3) . . . . ?
N5 N6 C38 C40 -179.7(2) . . . . ?
N5 C32 C33 C34 -112.8(3) . . . . ?
N6 N5 C32 C24 177.4(2) . . . . ?
N6 N5 C32 C33 -7.7(3) . . . . ?
C21 O4 C25 N4 174.7(2) . . . . ?
C21 O4 C25 C24 -4.1(3) . . . . ?
C21 C22 C23 C24 -1.8(4) . . . . ?
C21 C22 C23 C26 177.6(2) . . . . ?
C22 C23 C24 C25 3.7(3) . . . . ?
C22 C23 C24 C32 -172.4(3) . . . . ?
C22 C23 C26 C27 47.9(3) . . . . ?
C22 C23 C26 C31 -132.1(3) . . . . ?
C23 C24 C25 O4 -0.8(3) . . . . ?
C23 C24 C25 N4 -179.7(2) . . . . ?
C23 C24 C32 N5 179.1(3) . . . . ?
C23 C24 C32 C33 5.2(5) . . . . ?
C23 C26 C27 C28 177.7(2) . . . . ?
C23 C26 C31 C30 -178.3(2) . . . . ?
C24 C23 C26 C27 -132.7(3) . . . . ?
C24 C23 C26 C31 47.4(3) . . . . ?
C24 C32 C33 C34 60.4(4) . . . . ?
C25 O4 C21 O3 -177.3(2) . . . . ?
C25 O4 C21 C22 5.8(3) . . . . ?
C25 N4 N5 N6 -178.9(2) . . . . ?
C25 N4 N5 C32 0.8(3) . . . . ?
C25 C24 C32 N5 2.6(2) . . . . ?
C25 C24 C32 C33 -171.3(2) . . . . ?
C26 C23 C24 C25 -175.7(2) . . . . ?
C26 C23 C24 C32 8.2(4) . . . . ?
C26 C27 C28 C29 1.0(4) . . . . ?
C27 C26 C31 C30 1.7(4) . . . . ?
C27 C28 C29 C30 0.9(5) . . . . ?
C28 C29 C30 C31 -1.6(5) . . . . ?
C29 C30 C31 C26 0.2(4) . . . . ?
C31 C26 C27 C28 -2.3(4) . . . . ?
C32 N5 N6 C35 -107.0(2) . . . . ?
C32 N5 N6 C38 123.0(2) . . . . ?
C32 C24 C25 O4 176.5(2) . . . . ?
C32 C24 C25 N4 -2.4(3) . . . . ?
C35 N6 C38 C39 173.5(2) . . . . ?
C35 N6 C38 C40 52.9(3) . . . . ?
C38 N6 C35 C36 -176.8(2) . . . . ?
C38 N6 C35 C37 56.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 2.437
_oxdiff_exptl_absorpt_empirical_full_min 0.654
####################################################################### 
# 
# 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_jft-r318
_database_code_depnum_ccdc_archive 'CCDC 2075642'
loop_
_audit_author_name
_audit_author_address
'Farzaneh Fadaei Tirani'
;EPFL ISIC
Switzerland
;
_audit_update_record             
;
2021-04-06 deposited with the CCDC.	2021-06-04 downloaded from the CCDC.
;
_audit_creation_date             2020-11-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H10 F2 O2'
_chemical_formula_sum            'C17 H10 F2 O2'
_chemical_formula_weight         284.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C17 H10 F2 O2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   6.16235(12)
_cell_length_b                   18.5749(4)
_cell_length_c                   11.4059(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.2906(17)
_cell_angle_gamma                90
_cell_volume                     1295.03(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6933
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      72.6310
_cell_measurement_theta_min      4.5290
_shelx_estimated_absorpt_T_max   0.962
_shelx_estimated_absorpt_T_min   0.710
_exptl_absorpt_coefficient_mu    0.970
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.340
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.41.89a (Rigaku Oxford Diffraction, 2020)
 Numerical absorption correction based on Gaussian integration over
 a multifaceted crystal model.
 Empirical absorption correction using spherical harmonics
 as implemented in SCALE3 ABSPACK scaling algorithm
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.0230
0 -1 0 0.0148
0 0 1 0.1799
0 0 -1 0.1645
1 0 -2 0.1065
1 0 0 0.1908
-1 0 2 0.1268
-1 0 -2 0.1609
-1 0 1 0.1324
1 1 1 0.1877

_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.04
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0001 1.0000 0.0003 -0.0818 -0.0126 -0.0051
-0.0001 -1.0000 -0.0003 0.0818 0.0126 0.0051
-0.0002 0.0005 1.0001 -0.0035 0.0699 -0.1168
0.0002 -0.0005 -1.0001 0.0035 -0.0699 0.1168
1.0005 -0.0010 -1.9998 0.0468 -0.3346 0.0787
1.0000 -0.0000 0.0003 0.0397 -0.1947 -0.1549
-1.0005 0.0010 1.9998 -0.0468 0.3346 -0.0787
-0.9995 -0.0010 -2.0004 -0.0326 0.0549 0.3886
-1.0002 0.0005 0.9998 -0.0433 0.2647 0.0381
0.9999 1.0005 1.0006 -0.0456 -0.1375 -0.2769

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11023
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.568
_diffrn_reflns_theta_min         4.576
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2665
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -114.00 -89.00   1.00    1.00    --  -43.13-143.00 -19.00   25
  2  ω    -87.00 -13.00   1.00    1.00    --  -43.13 127.00-133.00   74
  3  ω    -78.00 -53.00   1.00    1.00    --  -43.13 143.00  36.00   25
  4  ω     49.00  74.00   1.00    1.00    --   43.13-143.00 -19.00   25
  5  ω     64.00  89.00   1.00    1.00    --   43.13-127.00 150.00   25
  6  ω     60.00 114.00   1.00    4.00    --  103.80-127.00 150.00   54
  7  ω    105.00 130.00   1.00    4.00    --  103.80 143.00  36.00   25
  8  ω    112.00 137.00   1.00    4.00    --  103.80 127.00-133.00   25
  9  ω     72.00 107.00   1.00    4.00    --  103.80-143.00 -19.00   35
 10  ω   -102.00 -20.00   1.00    1.00    --  -43.13 -37.00  30.00   82
 11  ω   -122.00 -12.00   1.00    1.00    --  -43.13 -19.00 120.00  110
 12  ω     12.00  40.00   1.00    1.00    --   43.13  81.00  23.21   28
 13  ω     46.00 129.00   1.00    4.00    --  103.80 -45.00 120.00   83
 14  ω     43.00  69.00   1.00    4.00    --  103.80 -77.00 -60.00   26
 15  ω     22.00 106.00   1.00    4.00    --  103.80 -94.00 150.00   84
 16  ω     67.00  92.00   1.00    4.00    --  103.80 178.00 -30.00   25
 17  ω    104.00 170.00   1.00    4.00    --  103.80  77.00  90.00   66
 18  ω    104.00 131.00   1.00    4.00    --  103.80  77.00-180.00   27
 19  ω    113.00 144.00   1.00    4.00    --  103.80 178.00 -30.00   31
 20  ω     28.00  83.00   1.00    4.00    --  103.80-111.00  60.00   55
 21  ω     77.00 150.00   1.00    4.00    --  103.80  30.00  90.00   73
 22  ω    104.00 130.00   1.00    4.00    --  103.80  77.00-120.00   26
 23  ω    149.00 174.00   1.00    4.00    --  103.80  77.00-120.00   25
 24  ω    116.00 177.00   1.00    4.00    --  103.80 111.00 120.00   61
 25  ω     28.00 108.00   1.00    4.00    --  103.80-111.00 -30.00   80
 26  ω     51.00 108.00   1.00    4.00    --  103.80-111.00  90.00   57
 27  ω     78.00 173.00   1.00    4.00    --  103.80  30.00-180.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0397285000
_diffrn_orient_matrix_UB_12      -0.0817994000
_diffrn_orient_matrix_UB_13      -0.0034888000
_diffrn_orient_matrix_UB_21      -0.1947620000
_diffrn_orient_matrix_UB_22      -0.0126400000
_diffrn_orient_matrix_UB_23      0.0698771000
_diffrn_orient_matrix_UB_31      -0.1549109000
_diffrn_orient_matrix_UB_32      -0.0050878000
_diffrn_orient_matrix_UB_33      -0.1168555000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2298
_reflns_number_total             2543
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT 2018/2 (Sheldrick, 2015)'
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2543
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0313
_refine_ls_restrained_S_all      1.044
_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)+(0.0348P)²+0.3304P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0822
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14),
 C16(H16), C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.49868(14) 0.92596(4) 0.55665(7) 0.0424(2) Uani 1 1 d . . . . .
F2 F 0.46871(14) 0.45177(4) 0.88673(7) 0.0431(2) Uani 1 1 d . . . . .
O1 O 0.63592(14) 0.83585(5) 0.66266(8) 0.0334(2) Uani 1 1 d . . . . .
O2 O 0.80267(14) 0.74817(5) 0.77034(8) 0.0388(2) Uani 1 1 d . . . . .
C1 C 0.64473(19) 0.76399(7) 0.70224(10) 0.0298(3) Uani 1 1 d . . . . .
C2 C 0.4740(2) 0.85693(7) 0.58152(11) 0.0321(3) Uani 1 1 d . . . . .
C3 C 0.3126(2) 0.81587(6) 0.53115(10) 0.0300(3) Uani 1 1 d . . . . .
H3 H 0.205323 0.834316 0.471539 0.036 Uiso 1 1 calc R U . . .
C4 C 0.30586(18) 0.74238(6) 0.57008(9) 0.0251(2) Uani 1 1 d . . . . .
C5 C 0.46307(18) 0.71770(6) 0.65664(9) 0.0258(2) Uani 1 1 d . . . . .
C6 C 0.12733(18) 0.69637(6) 0.51012(9) 0.0248(2) Uani 1 1 d . . . . .
C7 C -0.07865(19) 0.72633(7) 0.47587(10) 0.0298(3) Uani 1 1 d . . . . .
H7 H -0.105475 0.775041 0.494930 0.036 Uiso 1 1 calc R U . . .
C8 C -0.2448(2) 0.68576(8) 0.41427(11) 0.0377(3) Uani 1 1 d . . . . .
H8 H -0.384486 0.706685 0.391483 0.045 Uiso 1 1 calc R U . . .
C9 C -0.2068(2) 0.61483(8) 0.38612(11) 0.0393(3) Uani 1 1 d . . . . .
H9 H -0.320649 0.586896 0.344513 0.047 Uiso 1 1 calc R U . . .
C10 C -0.0019(2) 0.58440(7) 0.41869(11) 0.0355(3) Uani 1 1 d . . . . .
H10 H 0.024192 0.535742 0.398991 0.043 Uiso 1 1 calc R U . . .
C11 C 0.16451(19) 0.62493(7) 0.47991(10) 0.0289(3) Uani 1 1 d . . . . .
H11 H 0.304556 0.603996 0.501412 0.035 Uiso 1 1 calc R U . . .
C12 C 0.46318(18) 0.64609(6) 0.71391(9) 0.0260(2) Uani 1 1 d . . . . .
C13 C 0.63976(19) 0.59898(7) 0.71378(10) 0.0311(3) Uani 1 1 d . . . . .
H13 H 0.759955 0.612136 0.673759 0.037 Uiso 1 1 calc R U . . .
C14 C 0.6416(2) 0.53325(7) 0.77138(11) 0.0340(3) Uani 1 1 d . . . . .
H14 H 0.761243 0.501036 0.770936 0.041 Uiso 1 1 calc R U . . .
C15 C 0.4659(2) 0.51577(7) 0.82925(10) 0.0322(3) Uani 1 1 d . . . . .
C16 C 0.2881(2) 0.56036(7) 0.83097(11) 0.0319(3) Uani 1 1 d . . . . .
H16 H 0.168481 0.546544 0.870968 0.038 Uiso 1 1 calc R U . . .
C17 C 0.28759(18) 0.62595(6) 0.77295(10) 0.0277(3) Uani 1 1 d . . . . .
H17 H 0.166453 0.657542 0.773375 0.033 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C2 1.3260(15) . ?
F2 C15 1.3566(14) . ?
O1 C1 1.4080(15) . ?
O1 C2 1.3306(16) . ?
O2 C1 1.2021(15) . ?
C1 C5 1.4544(15) . ?
C2 C3 1.3252(18) . ?
C3 H3 0.9500 . ?
C3 C4 1.4378(16) . ?
C4 C5 1.3714(16) . ?
C4 C6 1.4891(15) . ?
C5 C12 1.4819(16) . ?
C6 C7 1.3956(15) . ?
C6 C11 1.3971(16) . ?
C7 H7 0.9500 . ?
C7 C8 1.3884(18) . ?
C8 H8 0.9500 . ?
C8 C9 1.383(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.390(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.3871(17) . ?
C11 H11 0.9500 . ?
C12 C13 1.3965(17) . ?
C12 C17 1.3962(16) . ?
C13 H13 0.9500 . ?
C13 C14 1.3858(18) . ?
C14 H14 0.9500 . ?
C14 C15 1.3768(19) . ?
C15 C16 1.3757(18) . ?
C16 H16 0.9500 . ?
C16 C17 1.3862(17) . ?
C17 H17 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C1 119.80(9) . . ?
O1 C1 C5 116.69(10) . . ?
O2 C1 O1 115.72(10) . . ?
O2 C1 C5 127.59(12) . . ?
F1 C2 O1 109.70(10) . . ?
C3 C2 F1 124.31(12) . . ?
C3 C2 O1 125.98(12) . . ?
C2 C3 H3 121.2 . . ?
C2 C3 C4 117.51(11) . . ?
C4 C3 H3 121.2 . . ?
C3 C4 C6 116.85(10) . . ?
C5 C4 C3 119.62(10) . . ?
C5 C4 C6 123.51(10) . . ?
C1 C5 C12 114.57(10) . . ?
C4 C5 C1 120.08(11) . . ?
C4 C5 C12 125.32(10) . . ?
C7 C6 C4 119.50(10) . . ?
C7 C6 C11 118.78(10) . . ?
C11 C6 C4 121.58(10) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 C6 120.76(12) . . ?
C8 C7 H7 119.6 . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 119.90(12) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 120.02(11) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.15(12) . . ?
C11 C10 H10 119.9 . . ?
C6 C11 H11 119.8 . . ?
C10 C11 C6 120.38(11) . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C5 121.25(11) . . ?
C17 C12 C5 119.74(10) . . ?
C17 C12 C13 118.97(11) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.74(11) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 120.8 . . ?
C15 C14 C13 118.39(11) . . ?
C15 C14 H14 120.8 . . ?
F2 C15 C14 118.41(11) . . ?
F2 C15 C16 118.83(12) . . ?
C16 C15 C14 122.76(12) . . ?
C15 C16 H16 120.8 . . ?
C15 C16 C17 118.42(11) . . ?
C17 C16 H16 120.8 . . ?
C12 C17 H17 119.6 . . ?
C16 C17 C12 120.72(11) . . ?
C16 C17 H17 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C2 C3 C4 -178.46(11) . . . . ?
F2 C15 C16 C17 179.39(10) . . . . ?
O1 C1 C5 C4 6.67(16) . . . . ?
O1 C1 C5 C12 -171.42(9) . . . . ?
O1 C2 C3 C4 2.34(19) . . . . ?
O2 C1 C5 C4 -173.43(12) . . . . ?
O2 C1 C5 C12 8.48(18) . . . . ?
C1 O1 C2 F1 -179.46(9) . . . . ?
C1 O1 C2 C3 -0.16(18) . . . . ?
C1 C5 C12 C13 -58.23(14) . . . . ?
C1 C5 C12 C17 119.44(12) . . . . ?
C2 O1 C1 O2 175.79(11) . . . . ?
C2 O1 C1 C5 -4.30(15) . . . . ?
C2 C3 C4 C5 0.24(17) . . . . ?
C2 C3 C4 C6 -178.23(11) . . . . ?
C3 C4 C5 C1 -4.70(16) . . . . ?
C3 C4 C5 C12 173.16(11) . . . . ?
C3 C4 C6 C7 -36.21(15) . . . . ?
C3 C4 C6 C11 139.39(11) . . . . ?
C4 C5 C12 C13 123.80(13) . . . . ?
C4 C5 C12 C17 -58.53(16) . . . . ?
C4 C6 C7 C8 176.56(11) . . . . ?
C4 C6 C11 C10 -176.68(11) . . . . ?
C5 C4 C6 C7 145.38(11) . . . . ?
C5 C4 C6 C11 -39.02(16) . . . . ?
C5 C12 C13 C14 177.59(10) . . . . ?
C5 C12 C17 C16 -177.53(10) . . . . ?
C6 C4 C5 C1 173.67(10) . . . . ?
C6 C4 C5 C12 -8.47(18) . . . . ?
C6 C7 C8 C9 -0.08(19) . . . . ?
C7 C6 C11 C10 -1.05(17) . . . . ?
C7 C8 C9 C10 -0.5(2) . . . . ?
C8 C9 C10 C11 0.3(2) . . . . ?
C9 C10 C11 C6 0.50(19) . . . . ?
C11 C6 C7 C8 0.84(17) . . . . ?
C12 C13 C14 C15 -0.39(18) . . . . ?
C13 C12 C17 C16 0.19(17) . . . . ?
C13 C14 C15 F2 -179.29(10) . . . . ?
C13 C14 C15 C16 0.81(19) . . . . ?
C14 C15 C16 C17 -0.72(18) . . . . ?
C15 C16 C17 C12 0.20(17) . . . . ?
C17 C12 C13 C14 -0.09(17) . . . . ?

_olex2_date_sample_data_collection 2020-11-26
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.520
_oxdiff_exptl_absorpt_empirical_full_min 0.668
####################################################################### 
# 
# 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_jft-r386
_database_code_depnum_ccdc_archive 'CCDC 2075646'
loop_
_audit_author_name
_audit_author_address
'Farzaneh Fadaei Tirani'
;EPFL ISIC
Switzerland
;
_audit_update_record             
;
2021-04-06 deposited with the CCDC.	2021-06-04 downloaded from the CCDC.
;
_audit_creation_date             2021-02-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H11 Cl O2'
_chemical_formula_sum            'C17 H11 Cl O2'
_chemical_formula_weight         282.71
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C17 H11 Cl O2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.9105(3)
_cell_length_b                   9.8857(3)
_cell_length_c                   17.5630(4)
_cell_angle_alpha                83.587(2)
_cell_angle_beta                 81.245(3)
_cell_angle_gamma                85.103(3)
_cell_volume                     1345.68(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5533
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      72.3910
_cell_measurement_theta_min      4.9550
_shelx_estimated_absorpt_T_max   0.929
_shelx_estimated_absorpt_T_min   0.623
_exptl_absorpt_coefficient_mu    2.492
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.482
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on Gaussian integration over
a multifaceted crystal model.
Empirical absorption correction using spherical harmonics
as implemented in SCALE3 ABSPACK scaling algorithm
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0859
0 0 -1 0.1173
0 1 0 0.0769
0 -1 0 0.0829
2 -1 1 0.0296
-2 1 -1 0.0042
0 -1 -1 0.0847
0 1 -1 0.0914
0 1 2 0.1003
0 -2 -1 0.0783

_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.03
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0006 0.0009 1.0004 -0.0100 -0.0367 0.0807
0.0006 -0.0009 -1.0004 0.0100 0.0367 -0.0807
0.0013 1.0001 -0.0024 -0.1392 -0.0469 -0.0560
-0.0013 -1.0001 0.0024 0.1392 0.0469 0.0560
1.9968 -1.0013 1.0072 0.0025 0.3739 0.2233
-1.9968 1.0013 -1.0072 -0.0025 -0.3739 -0.2233
-0.0007 -1.0010 -0.9979 0.1492 0.0836 -0.0247
0.0019 0.9991 -1.0028 -0.1292 -0.0102 -0.1367
0.0001 1.0020 1.9983 -0.1592 -0.1203 0.1054
-0.0020 -2.0011 -0.9955 0.2885 0.1305 0.0313

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10445
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.527
_diffrn_reflns_theta_min         4.512
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2817
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00  30.00   1.00    3.00    --  -40.91  34.00 154.00   95
  2  ω    -89.00 -42.00   1.00    3.00    --  -40.91 -34.00  -3.00   47
  3  ω     -8.00  17.00   1.00    3.00    --   40.91 -34.00  -3.00   25
  4  ω     42.00  67.00   1.00    3.00    --   40.91  34.00 154.00   25
  5  ω     31.00 128.00   1.00   12.00    --  105.15 -34.00  -3.00   97
  6  ω    105.00 142.00   1.00   12.00    --  105.15  34.00 154.00   37
  7  ω    -78.00  -6.00   1.00    3.00    --  -40.91 125.00-180.00   72
  8  ω     44.00  71.00   1.00    3.00    --   40.91-125.00-180.00   27
  9  ω     27.00  67.00   1.00    3.00    --   40.91-125.00 -60.00   40
 10  ω     46.00  95.00   1.00    3.00    --   40.91-125.00  30.00   49
 11  ω     16.00 115.00   1.00    3.00    --   40.91  38.00   0.00   99
 12  ω     31.00  58.00   1.00   12.00    --  105.15-111.00-180.00   27
 13  ω    104.00 162.00   1.00   12.00    --  105.15  77.00   0.00   58
 14  ω     43.00 134.00   1.00   12.00    --  105.15 -61.00  90.00   91
 15  ω    111.00 178.00   1.00   12.00    --  105.15  77.00  30.00   67
 16  ω    140.00 170.00   1.00   12.00    --  105.15 111.00  90.00   30
 17  ω    120.00 176.00   1.00   12.00    --  105.15  77.00 150.00   56
 18  ω     30.00 107.00   1.00   12.00    --  105.15-111.00  30.00   77
 19  ω     55.00 107.00   1.00   12.00    --  105.15-111.00  90.00   52
 20  ω     68.00 105.00   1.00   12.00    --  105.15-111.00 -60.00   37
 21  ω     89.00 176.00   1.00   12.00    --  105.15  45.00 -30.00   87
 22  ω     80.00 109.00   1.00   12.00    --  105.15-111.00-180.00   29
 23  ω    115.00 178.00   1.00   12.00    --  105.15  77.00  60.00   63
 24  ω     45.00  90.00   1.00   12.00    --  105.15 -94.00-120.00   45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0635383000
_diffrn_orient_matrix_UB_12      -0.1391484000
_diffrn_orient_matrix_UB_13      -0.0099117000
_diffrn_orient_matrix_UB_21      0.1819910000
_diffrn_orient_matrix_UB_22      -0.0472312000
_diffrn_orient_matrix_UB_23      -0.0365385000
_diffrn_orient_matrix_UB_31      0.0430999000
_diffrn_orient_matrix_UB_32      -0.0558456000
_diffrn_orient_matrix_UB_33      0.0807669000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4471
_reflns_number_total             5170
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT 2018/2 (Sheldrick, 2015)'
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         5170
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0347
_refine_ls_restrained_S_all      1.027
_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)+(0.0516P)²+0.1922P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.0938
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14),
 C15(H15), C16(H16), C17(H17), C20(H20), C24(H24), C25(H25), C26(H26), C27(H27),
  C28(H28), C30(H30), C31(H31), C32(H32), C33(H33), C34(H34)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.44937(5) 0.83909(4) 0.54376(2) 0.03737(11) Uani 1 1 d . . . . .
O1 O 1.29073(14) 0.82101(11) 0.68102(6) 0.0305(2) Uani 1 1 d . . . . .
O2 O 1.18506(15) 0.82302(12) 0.80438(6) 0.0332(2) Uani 1 1 d . . . . .
C1 C 1.16490(19) 0.78544(15) 0.74362(8) 0.0267(3) Uani 1 1 d . . . . .
C2 C 1.2826(2) 0.78449(16) 0.60997(9) 0.0286(3) Uani 1 1 d . . . . .
C3 C 1.1587(2) 0.71279(16) 0.59435(9) 0.0288(3) Uani 1 1 d . . . . .
H3 H 1.158971 0.689049 0.543385 0.035 Uiso 1 1 calc R U . . .
C4 C 1.02504(19) 0.67188(14) 0.65550(8) 0.0248(3) Uani 1 1 d . . . . .
C5 C 1.02496(19) 0.71004(14) 0.72857(8) 0.0249(3) Uani 1 1 d . . . . .
C6 C 0.89571(19) 0.58618(15) 0.63528(8) 0.0254(3) Uani 1 1 d . . . . .
C7 C 0.8394(2) 0.47277(15) 0.68476(8) 0.0269(3) Uani 1 1 d . . . . .
H7 H 0.881203 0.451384 0.732913 0.032 Uiso 1 1 calc R U . . .
C8 C 0.7228(2) 0.39137(15) 0.66385(9) 0.0306(3) Uani 1 1 d . . . . .
H8 H 0.686135 0.314129 0.697567 0.037 Uiso 1 1 calc R U . . .
C9 C 0.6599(2) 0.42216(17) 0.59415(10) 0.0338(3) Uani 1 1 d . . . . .
H9 H 0.579066 0.366954 0.580254 0.041 Uiso 1 1 calc R U . . .
C10 C 0.7155(2) 0.53430(17) 0.54462(9) 0.0339(3) Uani 1 1 d . . . . .
H10 H 0.672337 0.555839 0.496794 0.041 Uiso 1 1 calc R U . . .
C11 C 0.8337(2) 0.61496(16) 0.56463(9) 0.0302(3) Uani 1 1 d . . . . .
H11 H 0.872644 0.690365 0.529941 0.036 Uiso 1 1 calc R U . . .
C12 C 0.88515(19) 0.68997(14) 0.79456(8) 0.0260(3) Uani 1 1 d . . . . .
C13 C 0.7163(2) 0.73468(15) 0.78523(9) 0.0280(3) Uani 1 1 d . . . . .
H13 H 0.690171 0.769157 0.735370 0.034 Uiso 1 1 calc R U . . .
C14 C 0.5868(2) 0.72920(17) 0.84805(9) 0.0333(3) Uani 1 1 d . . . . .
H14 H 0.472777 0.760820 0.841115 0.040 Uiso 1 1 calc R U . . .
C15 C 0.6231(2) 0.67764(17) 0.92103(10) 0.0359(4) Uani 1 1 d . . . . .
H15 H 0.534466 0.674393 0.964116 0.043 Uiso 1 1 calc R U . . .
C16 C 0.7894(2) 0.63096(16) 0.93068(9) 0.0339(3) Uani 1 1 d . . . . .
H16 H 0.814142 0.594671 0.980497 0.041 Uiso 1 1 calc R U . . .
C17 C 0.9203(2) 0.63670(16) 0.86820(9) 0.0299(3) Uani 1 1 d . . . . .
H17 H 1.033865 0.604409 0.875462 0.036 Uiso 1 1 calc R U . . .
Cl2 Cl 1.18651(6) 1.00528(4) 0.41060(2) 0.04026(12) Uani 1 1 d . . . . .
O3 O 0.92906(15) 0.88474(12) 0.38968(6) 0.0333(3) Uani 1 1 d . . . . .
O4 O 0.69776(18) 0.77346(15) 0.39107(7) 0.0455(3) Uani 1 1 d . . . . .
C18 C 0.8195(2) 0.82065(16) 0.35084(9) 0.0311(3) Uani 1 1 d . . . . .
C19 C 1.0709(2) 0.93957(15) 0.35066(9) 0.0291(3) Uani 1 1 d . . . . .
C20 C 1.1171(2) 0.94012(14) 0.27435(8) 0.0270(3) Uani 1 1 d . . . . .
H20 H 1.217830 0.981512 0.249477 0.032 Uiso 1 1 calc R U . . .
C21 C 1.01180(19) 0.87684(14) 0.23026(8) 0.0243(3) Uani 1 1 d . . . . .
C22 C 0.8659(2) 0.81986(14) 0.26740(8) 0.0256(3) Uani 1 1 d . . . . .
C23 C 1.07424(18) 0.87446(15) 0.14625(8) 0.0248(3) Uani 1 1 d . . . . .
C24 C 1.13993(19) 0.99114(15) 0.10367(8) 0.0272(3) Uani 1 1 d . . . . .
H24 H 1.140192 1.071865 0.128349 0.033 Uiso 1 1 calc R U . . .
C25 C 1.2047(2) 0.99041(16) 0.02584(9) 0.0313(3) Uani 1 1 d . . . . .
H25 H 1.247391 1.070803 -0.002731 0.038 Uiso 1 1 calc R U . . .
C26 C 1.2073(2) 0.87250(17) -0.01038(9) 0.0325(3) Uani 1 1 d . . . . .
H26 H 1.251331 0.871997 -0.063791 0.039 Uiso 1 1 calc R U . . .
C27 C 1.1453(2) 0.75518(17) 0.03165(9) 0.0321(3) Uani 1 1 d . . . . .
H27 H 1.149023 0.673895 0.007077 0.039 Uiso 1 1 calc R U . . .
C28 C 1.0781(2) 0.75583(15) 0.10918(9) 0.0286(3) Uani 1 1 d . . . . .
H28 H 1.034494 0.675416 0.137317 0.034 Uiso 1 1 calc R U . . .
C29 C 0.74431(19) 0.75619(15) 0.22755(8) 0.0261(3) Uani 1 1 d . . . . .
C30 C 0.7209(2) 0.61713(16) 0.24236(9) 0.0317(3) Uani 1 1 d . . . . .
H30 H 0.777886 0.563374 0.280379 0.038 Uiso 1 1 calc R U . . .
C31 C 0.6149(2) 0.55661(17) 0.20189(10) 0.0357(4) Uani 1 1 d . . . . .
H31 H 0.602416 0.461211 0.211163 0.043 Uiso 1 1 calc R U . . .
C32 C 0.5274(2) 0.63505(18) 0.14802(10) 0.0355(4) Uani 1 1 d . . . . .
H32 H 0.455448 0.593538 0.120102 0.043 Uiso 1 1 calc R U . . .
C33 C 0.5452(2) 0.77447(18) 0.13503(9) 0.0352(3) Uani 1 1 d . . . . .
H33 H 0.482941 0.828860 0.099157 0.042 Uiso 1 1 calc R U . . .
C34 C 0.6542(2) 0.83499(16) 0.17441(9) 0.0306(3) Uani 1 1 d . . . . .
H34 H 0.666844 0.930349 0.164915 0.037 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C2 1.7026(16) . ?
O1 C1 1.4013(19) . ?
O1 C2 1.3492(19) . ?
O2 C1 1.2053(18) . ?
C1 C5 1.458(2) . ?
C2 C3 1.335(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.437(2) . ?
C4 C5 1.377(2) . ?
C4 C6 1.489(2) . ?
C5 C12 1.484(2) . ?
C6 C7 1.400(2) . ?
C6 C11 1.394(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.389(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.384(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.389(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.387(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.398(2) . ?
C12 C17 1.400(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.387(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.388(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.385(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.389(2) . ?
C17 H17 0.9500 . ?
Cl2 C19 1.7073(15) . ?
O3 C18 1.4100(19) . ?
O3 C19 1.345(2) . ?
O4 C18 1.200(2) . ?
C18 C22 1.456(2) . ?
C19 C20 1.334(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.442(2) . ?
C21 C22 1.369(2) . ?
C21 C23 1.485(2) . ?
C22 C29 1.489(2) . ?
C23 C24 1.397(2) . ?
C23 C28 1.399(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.385(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.386(2) . ?
C26 H26 0.9500 . ?
C26 C27 1.388(2) . ?
C27 H27 0.9500 . ?
C27 C28 1.385(2) . ?
C28 H28 0.9500 . ?
C29 C30 1.393(2) . ?
C29 C34 1.390(2) . ?
C30 H30 0.9500 . ?
C30 C31 1.389(2) . ?
C31 H31 0.9500 . ?
C31 C32 1.386(2) . ?
C32 H32 0.9500 . ?
C32 C33 1.387(2) . ?
C33 H33 0.9500 . ?
C33 C34 1.393(2) . ?
C34 H34 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C1 120.70(12) . . ?
O1 C1 C5 117.51(12) . . ?
O2 C1 O1 115.09(13) . . ?
O2 C1 C5 127.39(14) . . ?
O1 C2 Cl1 111.99(11) . . ?
C3 C2 Cl1 124.50(12) . . ?
C3 C2 O1 123.51(14) . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.24(14) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C6 116.64(13) . . ?
C5 C4 C3 119.44(13) . . ?
C5 C4 C6 123.90(13) . . ?
C1 C5 C12 114.98(12) . . ?
C4 C5 C1 119.53(14) . . ?
C4 C5 C12 125.33(13) . . ?
C7 C6 C4 121.15(13) . . ?
C11 C6 C4 120.01(13) . . ?
C11 C6 C7 118.79(14) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.39(14) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.36(14) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 120.2 . . ?
C8 C9 C10 119.60(14) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.37(14) . . ?
C11 C10 H10 119.8 . . ?
C6 C11 H11 119.8 . . ?
C10 C11 C6 120.48(14) . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C5 119.87(13) . . ?
C13 C12 C17 118.74(14) . . ?
C17 C12 C5 121.19(14) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.66(14) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.19(16) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.63(15) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.61(15) . . ?
C17 C16 H16 119.7 . . ?
C12 C17 H17 119.9 . . ?
C16 C17 C12 120.15(15) . . ?
C16 C17 H17 119.9 . . ?
C19 O3 C18 120.68(12) . . ?
O3 C18 C22 116.84(13) . . ?
O4 C18 O3 115.45(14) . . ?
O4 C18 C22 127.71(15) . . ?
O3 C19 Cl2 111.99(11) . . ?
C20 C19 Cl2 124.08(13) . . ?
C20 C19 O3 123.92(14) . . ?
C19 C20 H20 120.6 . . ?
C19 C20 C21 118.89(14) . . ?
C21 C20 H20 120.6 . . ?
C20 C21 C23 116.49(13) . . ?
C22 C21 C20 119.33(13) . . ?
C22 C21 C23 124.15(13) . . ?
C18 C22 C29 115.63(13) . . ?
C21 C22 C18 120.30(14) . . ?
C21 C22 C29 124.06(13) . . ?
C24 C23 C21 119.44(13) . . ?
C24 C23 C28 118.74(13) . . ?
C28 C23 C21 121.73(13) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 C23 120.71(14) . . ?
C25 C24 H24 119.6 . . ?
C24 C25 H25 120.0 . . ?
C24 C25 C26 120.06(14) . . ?
C26 C25 H25 120.0 . . ?
C25 C26 H26 120.1 . . ?
C25 C26 C27 119.76(14) . . ?
C27 C26 H26 120.1 . . ?
C26 C27 H27 119.8 . . ?
C28 C27 C26 120.44(15) . . ?
C28 C27 H27 119.8 . . ?
C23 C28 H28 119.9 . . ?
C27 C28 C23 120.27(14) . . ?
C27 C28 H28 119.9 . . ?
C30 C29 C22 120.55(13) . . ?
C34 C29 C22 120.18(13) . . ?
C34 C29 C30 119.27(14) . . ?
C29 C30 H30 119.8 . . ?
C31 C30 C29 120.40(15) . . ?
C31 C30 H30 119.8 . . ?
C30 C31 H31 119.9 . . ?
C32 C31 C30 120.15(15) . . ?
C32 C31 H31 119.9 . . ?
C31 C32 H32 120.1 . . ?
C31 C32 C33 119.72(15) . . ?
C33 C32 H32 120.1 . . ?
C32 C33 H33 119.9 . . ?
C32 C33 C34 120.24(15) . . ?
C34 C33 H33 119.9 . . ?
C29 C34 C33 120.16(15) . . ?
C29 C34 H34 119.9 . . ?
C33 C34 H34 119.9 . . ?

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
Cl1 C2 C3 C4 179.64(11) . . . . ?
O1 C1 C5 C4 2.8(2) . . . . ?
O1 C1 C5 C12 -172.91(12) . . . . ?
O1 C2 C3 C4 0.4(2) . . . . ?
O2 C1 C5 C4 -178.15(15) . . . . ?
O2 C1 C5 C12 6.2(2) . . . . ?
C1 O1 C2 Cl1 -179.95(10) . . . . ?
C1 O1 C2 C3 -0.6(2) . . . . ?
C1 C5 C12 C13 123.68(15) . . . . ?
C1 C5 C12 C17 -51.15(19) . . . . ?
C2 O1 C1 O2 179.85(13) . . . . ?
C2 O1 C1 C5 -1.0(2) . . . . ?
C2 C3 C4 C5 1.5(2) . . . . ?
C2 C3 C4 C6 -176.99(14) . . . . ?
C3 C4 C5 C1 -3.0(2) . . . . ?
C3 C4 C5 C12 172.17(13) . . . . ?
C3 C4 C6 C7 136.74(15) . . . . ?
C3 C4 C6 C11 -40.6(2) . . . . ?
C4 C5 C12 C13 -51.7(2) . . . . ?
C4 C5 C12 C17 133.47(15) . . . . ?
C4 C6 C7 C8 -177.92(14) . . . . ?
C4 C6 C11 C10 178.84(15) . . . . ?
C5 C4 C6 C7 -41.7(2) . . . . ?
C5 C4 C6 C11 140.96(15) . . . . ?
C5 C12 C13 C14 -173.55(14) . . . . ?
C5 C12 C17 C16 173.84(14) . . . . ?
C6 C4 C5 C1 175.35(13) . . . . ?
C6 C4 C5 C12 -9.5(2) . . . . ?
C6 C7 C8 C9 -0.6(2) . . . . ?
C7 C6 C11 C10 1.4(2) . . . . ?
C7 C8 C9 C10 0.8(2) . . . . ?
C8 C9 C10 C11 0.1(3) . . . . ?
C9 C10 C11 C6 -1.2(3) . . . . ?
C11 C6 C7 C8 -0.5(2) . . . . ?
C12 C13 C14 C15 -0.7(2) . . . . ?
C13 C12 C17 C16 -1.1(2) . . . . ?
C13 C14 C15 C16 -0.4(2) . . . . ?
C14 C15 C16 C17 0.7(2) . . . . ?
C15 C16 C17 C12 0.0(2) . . . . ?
C17 C12 C13 C14 1.4(2) . . . . ?
Cl2 C19 C20 C21 177.70(11) . . . . ?
O3 C18 C22 C21 1.4(2) . . . . ?
O3 C18 C22 C29 -177.75(13) . . . . ?
O3 C19 C20 C21 -1.0(2) . . . . ?
O4 C18 C22 C21 -178.97(17) . . . . ?
O4 C18 C22 C29 1.9(3) . . . . ?
C18 O3 C19 Cl2 -177.68(11) . . . . ?
C18 O3 C19 C20 1.1(2) . . . . ?
C18 C22 C29 C30 -65.76(19) . . . . ?
C18 C22 C29 C34 114.94(16) . . . . ?
C19 O3 C18 O4 179.05(15) . . . . ?
C19 O3 C18 C22 -1.3(2) . . . . ?
C19 C20 C21 C22 1.0(2) . . . . ?
C19 C20 C21 C23 -177.04(13) . . . . ?
C20 C21 C22 C18 -1.3(2) . . . . ?
C20 C21 C22 C29 177.78(13) . . . . ?
C20 C21 C23 C24 -43.40(19) . . . . ?
C20 C21 C23 C28 132.94(15) . . . . ?
C21 C22 C29 C30 115.14(17) . . . . ?
C21 C22 C29 C34 -64.2(2) . . . . ?
C21 C23 C24 C25 177.69(14) . . . . ?
C21 C23 C28 C27 -176.66(14) . . . . ?
C22 C21 C23 C24 138.61(15) . . . . ?
C22 C21 C23 C28 -45.0(2) . . . . ?
C22 C29 C30 C31 -176.33(15) . . . . ?
C22 C29 C34 C33 177.64(15) . . . . ?
C23 C21 C22 C18 176.65(14) . . . . ?
C23 C21 C22 C29 -4.3(2) . . . . ?
C23 C24 C25 C26 -1.0(2) . . . . ?
C24 C23 C28 C27 -0.3(2) . . . . ?
C24 C25 C26 C27 -0.2(2) . . . . ?
C25 C26 C27 C28 1.2(2) . . . . ?
C26 C27 C28 C23 -0.9(2) . . . . ?
C28 C23 C24 C25 1.2(2) . . . . ?
C29 C30 C31 C32 -1.9(3) . . . . ?
C30 C29 C34 C33 -1.7(2) . . . . ?
C30 C31 C32 C33 -0.4(3) . . . . ?
C31 C32 C33 C34 1.7(3) . . . . ?
C32 C33 C34 C29 -0.7(3) . . . . ?
C34 C29 C30 C31 3.0(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.976
_oxdiff_exptl_absorpt_empirical_full_min 0.505
