# Electronic Supplementary Material (ESI) for RSC Medicinal Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_19jlr002b
_database_code_depnum_ccdc_archive 'CCDC 1997201'
loop_
_audit_author_name
_audit_author_address
'Jurg Hauser'
;Department of Chemistry and Biochemistry, University of Bern
Switzerland
;
_audit_update_record             
;
2020-04-15 deposited with the CCDC.	2020-06-25 downloaded from the CCDC.
;
_audit_creation_date             2019-03-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            31
_chemical_name_systematic        
5-((4-((1s,4s)-4-(3-(trifluoromethyl)phenyl)cyclohexyl)piperazin-1-yl)methyl)pyridin-2(1H)-one
_chemical_formula_moiety         'C23 H30 F3 N3 O, 2(C2 F3 O2)'
_chemical_formula_sum            'C27 H30 F9 N3 O5'
_chemical_formula_weight         647.54
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
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                   8.23301(6)
_cell_length_b                   13.02347(14)
_cell_length_c                   13.57687(16)
_cell_angle_alpha                98.1817(9)
_cell_angle_beta                 92.5946(8)
_cell_angle_gamma                103.5389(8)
_cell_volume                     1396.21(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    23345
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      76.8250
_cell_measurement_theta_min      3.2950
_shelx_estimated_absorpt_T_max   0.947
_shelx_estimated_absorpt_T_min   0.731
_exptl_absorpt_coefficient_mu    1.285
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.548
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.39a (Rigaku Oxford Diffraction, 2019)
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             668
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.0452
0 -1 0 0.0452
1 -1 0 0.1130
-1 1 0 0.1130
0 0 -1 0.0213
0 0 1 0.0213
-1 0 0 0.1293
1 0 0 0.1293
0 -1 1 0.0360
0 1 -1 0.0360
-2 5 -4 0.0665
-1 5 0 0.0566

_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.043
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            32559
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.165
_diffrn_reflns_theta_min         3.300
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.976
_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  -9.00   0.50    0.44    --  -18.75 125.00-127.00  114
  2  ω     26.00 120.00   0.50    0.44    --   47.95  77.00 -30.00  188
  3  ω     78.00 174.00   0.50    1.76    --  107.11 146.00  39.00  192
  4  ω     92.00 174.00   0.50    1.76    --  107.11 125.00-127.00  164
  5  ω     94.00 174.00   0.50    1.76    --  107.11  15.00   0.00  160
  6  ω     95.00 174.00   0.50    1.76    --  107.11  45.00  90.00  158
  7  ω     94.00 174.00   0.50    1.76    --  107.11  15.00 -30.00  160
  8  ω     95.00 174.00   0.50    1.76    --  107.11  45.00-150.00  158
  9  ω     95.00 174.00   0.50    1.76    --  107.11  30.00-120.00  158
 10  ω     95.00 174.00   0.50    1.76    --  107.11  45.00 -90.00  158
 11  ω     95.00 133.00   0.50    1.76    --  107.11  45.00  60.00   76
 12  ω     94.00 174.00   0.50    1.76    --  107.11  15.00  60.00  160
 13  ω     95.00 174.00   0.50    1.76    --  107.11  30.00 150.00  158
 14  ω     85.00 174.00   0.50    1.76    --  107.11  77.00 150.00  178
 15  ω     32.00  96.00   0.50    0.44    --   47.95-125.00 155.00  128
 16  ω     35.00 117.00   0.50    1.76    --  107.11-125.00 155.00  164
 17  ω     43.00 109.00   0.50    0.44    --   47.95-146.00 -11.00  132
 18  ω     43.00 132.00   0.50    1.76    --  107.11-146.00 -11.00  178
 19  ω     35.00  68.00   0.50    1.76    --  107.11 -61.00 120.00   66
 20  ω     35.00  68.00   0.50    1.76    --  107.11 -61.00  60.00   66
 21  ω     35.00 109.00   0.50    1.76    --  107.11 -94.00   0.00  148
 22  ω     35.00 102.00   0.50    1.76    --  107.11 -77.00 -60.00  134
 23  ω     35.00  68.00   0.50    1.76    --  107.11 -61.00 -60.00   66
 24  ω     35.00  68.00   0.50    1.76    --  107.11 -61.00-120.00   66
 25  ω     35.00  68.00   0.50    1.76    --  107.11 -61.00-150.00   66
 26  ω     35.00  68.00   0.50    1.76    --  107.11 -61.00-180.00   66
 27  ω     35.00 102.00   0.50    1.76    --  107.11 -77.00-180.00  134
 28  ω     35.00 102.00   0.50    1.76    --  107.11 -77.00-150.00  134
 29  ω     35.00  68.00   0.50    1.76    --  107.11 -61.00 -30.00   66
 30  ω     35.00 109.00   0.50    1.76    --  107.11 -94.00  30.00  148
 31  ω     35.00 102.00   0.50    1.76    --  107.11 -77.00 120.00  134
 32  ω     35.00  68.00   0.50    1.76    --  107.11 -61.00  30.00   66
 33  ω     35.00 102.00   0.50    1.76    --  107.11 -77.00  30.00  134
 34  ω     33.00 120.00   0.50    0.44    --   47.95  57.00 -90.00  174
 35  ω     26.00 120.00   0.50    0.44    --   47.95  77.00 -90.00  188
 36  ω     26.00 120.00   0.50    0.44    --   47.95  77.00-180.00  188
 37  ω     26.00 120.00   0.50    0.44    --   47.95  77.00-150.00  188
 38  ω     26.00 120.00   0.50    0.44    --   47.95  77.00  30.00  188
 39  ω     26.00 120.00   0.50    0.44    --   47.95  77.00 120.00  188
 40  ω     26.00 120.00   0.50    0.44    --   47.95  77.00 150.00  188
 41  ω     26.00 120.00   0.50    0.44    --   47.95  77.00  60.00  188
 42  ω     26.00 120.00   0.50    0.44    --   47.95  77.00  90.00  188
 43  ω    -25.00  40.00   0.50    0.44    --   47.95 -38.00-180.00  130
 44  ω    -26.00  23.00   0.50    0.44    --   47.95 -19.00 -90.00   98
 45  ω    -25.00  40.00   0.50    0.44    --   47.95 -38.00  30.00  130
 46  ω    -26.00  23.00   0.50    0.44    --   47.95 -19.00  60.00   98
 47  ω    -78.00 -20.00   0.50    0.44    --  -18.75 146.00  39.00  116
 48  ω    -90.00  -5.00   0.50    0.44    --  -18.75 -45.00 -60.00  170
 49  ω    -90.00   5.00   0.50    0.44    --  -18.75 -77.00 150.00  190
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0127393000
_diffrn_orient_matrix_UB_12      0.0483501000
_diffrn_orient_matrix_UB_13      0.1112606000
_diffrn_orient_matrix_UB_21      -0.0418193000
_diffrn_orient_matrix_UB_22      -0.1133022000
_diffrn_orient_matrix_UB_23      0.0279558000
_diffrn_orient_matrix_UB_31      0.1881003000
_diffrn_orient_matrix_UB_32      0.0023076000
_diffrn_orient_matrix_UB_33      0.0083231000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5341
_reflns_number_total             5783
_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 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.684
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     434
_refine_ls_number_reflns         5783
_refine_ls_number_restraints     108
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0516
_refine_ls_restrained_S_all      1.054
_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)+(0.0661P)²+1.0041P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1368
_refine_ls_wR_factor_ref         0.1392
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Uiso/Uaniso restraints and constraints
F1 \\sim F2 \\sim F3 \\sim C23 \\sim F2A \\sim F3A \\sim F1A: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08
3. Rigid body (RIGU) restrains
 F3A, F3, C23, F2, F2A, F1, F1A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(F2A)=Sof(F3A)=Sof(F1A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C11(H11), C14(H14)
5.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C12(H12A,
 H12B), C13(H13A,H13B), C15(H15A,H15B), C16(H16A,H16B)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3A), C5(H5), C18(H18), C20(H20), C21(H21), C22(H22)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.3881(7) 1.0448(3) 0.2908(7) 0.086(2) Uani 0.620(15) 1 d . U P A 1
F2 F 0.3310(7) 0.9108(5) 0.1792(4) 0.0767(14) Uani 0.620(15) 1 d . U P A 1
F3 F 0.2513(9) 0.8991(8) 0.3253(7) 0.094(3) Uani 0.620(15) 1 d . U P A 1
O1 O -0.37547(16) -0.09677(10) -0.02684(10) 0.0359(3) Uani 1 1 d . . . . .
N1 N -0.33044(18) 0.05207(11) 0.09103(11) 0.0283(3) Uani 1 1 d . . . . .
N2 N 0.12760(17) 0.27603(11) 0.25860(10) 0.0243(3) Uani 1 1 d . . . . .
N3 N 0.46241(17) 0.41268(11) 0.25746(10) 0.0241(3) Uani 1 1 d . . . . .
C1 C -0.2843(2) -0.03689(13) 0.04457(13) 0.0267(3) Uani 1 1 d . . . . .
C2 C -0.1306(2) -0.05323(13) 0.08528(13) 0.0282(3) Uani 1 1 d . . . . .
H2A H -0.092070 -0.111722 0.057579 0.034 Uiso 1 1 calc R . . . .
C3 C -0.0403(2) 0.01607(13) 0.16416(13) 0.0289(3) Uani 1 1 d . . . . .
H3A H 0.058861 0.003713 0.189735 0.035 Uiso 1 1 calc R . . . .
C4 C -0.0938(2) 0.10659(13) 0.20822(12) 0.0269(3) Uani 1 1 d . . . . .
C5 C -0.2410(2) 0.12051(13) 0.16967(13) 0.0281(3) Uani 1 1 d . . . . .
H5 H -0.280893 0.178214 0.197938 0.034 Uiso 1 1 calc R . . . .
C6 C 0.0034(2) 0.18642(14) 0.29363(13) 0.0303(4) Uani 1 1 d . . . . .
H6A H 0.062876 0.150351 0.335434 0.036 Uiso 1 1 calc R . . . .
H6B H -0.073946 0.216182 0.333848 0.036 Uiso 1 1 calc R . . . .
C7 C 0.2613(2) 0.23754(13) 0.20502(13) 0.0288(3) Uani 1 1 d . . . . .
H7A H 0.210579 0.184293 0.147775 0.035 Uiso 1 1 calc R . . . .
H7B H 0.321221 0.204009 0.249097 0.035 Uiso 1 1 calc R . . . .
C8 C 0.3829(2) 0.32883(13) 0.17048(12) 0.0282(3) Uani 1 1 d . . . . .
H8A H 0.469159 0.302056 0.136292 0.034 Uiso 1 1 calc R . . . .
H8B H 0.324162 0.360085 0.123707 0.034 Uiso 1 1 calc R . . . .
C9 C 0.3285(2) 0.45191(14) 0.31102(13) 0.0290(3) Uani 1 1 d . . . . .
H9A H 0.270030 0.486384 0.267039 0.035 Uiso 1 1 calc R . . . .
H9B H 0.379300 0.504547 0.368662 0.035 Uiso 1 1 calc R . . . .
C10 C 0.2044(2) 0.36086(14) 0.34466(12) 0.0297(4) Uani 1 1 d . . . . .
H10A H 0.261137 0.330291 0.393007 0.036 Uiso 1 1 calc R . . . .
H10B H 0.116957 0.388057 0.377007 0.036 Uiso 1 1 calc R . . . .
C11 C 0.6003(2) 0.50030(13) 0.22764(12) 0.0253(3) Uani 1 1 d . . . . .
H11 H 0.672787 0.465135 0.186653 0.030 Uiso 1 1 calc R . . . .
C12 C 0.5328(2) 0.57171(13) 0.16492(13) 0.0284(3) Uani 1 1 d . . . . .
H12A H 0.461292 0.608671 0.203468 0.034 Uiso 1 1 calc R . . . .
H12B H 0.466310 0.528386 0.106225 0.034 Uiso 1 1 calc R . . . .
C13 C 0.6796(2) 0.65356(14) 0.13313(13) 0.0311(4) Uani 1 1 d . . . . .
H13A H 0.742589 0.615993 0.088301 0.037 Uiso 1 1 calc R . . . .
H13B H 0.635306 0.701151 0.096573 0.037 Uiso 1 1 calc R . . . .
C14 C 0.7987(2) 0.72043(14) 0.22117(13) 0.0289(4) Uani 1 1 d . . . . .
H14 H 0.898707 0.757983 0.192712 0.035 Uiso 1 1 calc R . . . .
C15 C 0.8559(2) 0.64438(14) 0.28449(15) 0.0330(4) Uani 1 1 d . . . . .
H15A H 0.922489 0.603928 0.245465 0.040 Uiso 1 1 calc R . . . .
H15B H 0.926510 0.686217 0.342384 0.040 Uiso 1 1 calc R . . . .
C16 C 0.7084(2) 0.56683(14) 0.31926(13) 0.0298(4) Uani 1 1 d . . . . .
H16A H 0.749104 0.520468 0.359088 0.036 Uiso 1 1 calc R . . . .
H16B H 0.642569 0.606284 0.360086 0.036 Uiso 1 1 calc R . . . .
C17 C 0.7317(2) 0.80597(13) 0.28343(13) 0.0285(3) Uani 1 1 d . . . . .
C18 C 0.5841(2) 0.83274(14) 0.25540(14) 0.0301(4) Uani 1 1 d . . . . .
H18 H 0.518116 0.794091 0.198698 0.036 Uiso 1 1 calc R . . . .
C19 C 0.5338(2) 0.91649(14) 0.31102(15) 0.0355(4) Uani 1 1 d . . . . .
C20 C 0.6286(3) 0.97574(17) 0.39511(18) 0.0461(5) Uani 1 1 d . . . . .
H20 H 0.594510 1.031893 0.431655 0.055 Uiso 1 1 calc R . . . .
C21 C 0.7755(3) 0.95014(19) 0.42421(18) 0.0514(6) Uani 1 1 d . . . . .
H21 H 0.840851 0.989156 0.480991 0.062 Uiso 1 1 calc R . . . .
H1 H -0.424(4) 0.067(2) 0.069(2) 0.062 Uiso 1 1 d R . . . .
H2 H 0.064(4) 0.304(2) 0.214(2) 0.062 Uiso 1 1 d R . . . .
H3 H 0.513(4) 0.383(2) 0.299(2) 0.062 Uiso 1 1 d R . . . .
C22 C 0.8258(2) 0.86660(17) 0.36914(16) 0.0405(4) Uani 1 1 d . . . . .
H22 H 0.924860 0.850516 0.389871 0.049 Uiso 1 1 calc R . . . .
C23 C 0.3731(3) 0.94159(17) 0.27917(18) 0.0445(5) Uani 1 1 d . U . . .
F7 F -0.1905(3) 0.45466(13) 0.00053(13) 0.0841(6) Uani 1 1 d . . . . .
F8 F -0.33279(17) 0.29669(17) -0.00653(12) 0.0803(6) Uani 1 1 d . . . . .
F9 F -0.15127(19) 0.33388(14) -0.10933(9) 0.0637(4) Uani 1 1 d . . . . .
O4 O -0.06130(18) 0.36688(11) 0.14792(10) 0.0393(3) Uani 1 1 d . . . . .
O5 O 0.04111(18) 0.27550(12) 0.02331(11) 0.0427(3) Uani 1 1 d . . . . .
C26 C -0.0518(2) 0.32972(14) 0.05861(13) 0.0294(4) Uani 1 1 d . . . . .
C27 C -0.1805(2) 0.35288(16) -0.01588(13) 0.0342(4) Uani 1 1 d . . . . .
F4 F 0.71745(19) 0.31334(11) 0.61345(9) 0.0540(4) Uani 1 1 d . . . . .
F5 F 0.89956(18) 0.39610(13) 0.52892(13) 0.0706(5) Uani 1 1 d . . . . .
F6 F 0.82195(19) 0.22556(11) 0.50036(9) 0.0544(4) Uani 1 1 d . . . . .
O2 O 0.6521(2) 0.29763(13) 0.35695(10) 0.0483(4) Uani 1 1 d . . . . .
O3 O 0.5289(2) 0.37154(16) 0.48005(14) 0.0642(5) Uani 1 1 d . . . . .
C24 C 0.6331(2) 0.32605(14) 0.44543(14) 0.0348(4) Uani 1 1 d . . . . .
C25 C 0.7660(2) 0.31283(14) 0.52239(13) 0.0307(4) Uani 1 1 d . . . . .
F2A F 0.3596(11) 0.9625(14) 0.1942(8) 0.092(4) Uani 0.380(15) 1 d . U P A 2
F3A F 0.2364(13) 0.8633(8) 0.2836(12) 0.086(3) Uani 0.380(15) 1 d . U P A 2
F1A F 0.3320(15) 1.0244(12) 0.3396(10) 0.106(4) Uani 0.380(15) 1 d . U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C23 1.306(4) . ?
F2 C23 1.364(5) . ?
F3 C23 1.264(6) . ?
O1 C1 1.247(2) . ?
N1 C1 1.380(2) . ?
N1 C5 1.352(2) . ?
N1 H1 0.89(3) . ?
N2 C6 1.509(2) . ?
N2 C7 1.490(2) . ?
N2 C10 1.491(2) . ?
N2 H2 0.95(3) . ?
N3 C8 1.498(2) . ?
N3 C9 1.496(2) . ?
N3 C11 1.524(2) . ?
N3 H3 0.88(3) . ?
C1 C2 1.431(2) . ?
C2 H2A 0.9300 . ?
C2 C3 1.361(2) . ?
C3 H3A 0.9300 . ?
C3 C4 1.417(2) . ?
C4 C5 1.359(2) . ?
C4 C6 1.500(2) . ?
C5 H5 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.510(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.512(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11 0.9800 . ?
C11 C12 1.525(2) . ?
C11 C16 1.524(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.536(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.532(2) . ?
C14 H14 0.9800 . ?
C14 C15 1.538(2) . ?
C14 C17 1.524(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.527(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.392(2) . ?
C17 C22 1.396(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.392(3) . ?
C19 C20 1.376(3) . ?
C19 C23 1.495(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.383(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.386(3) . ?
C22 H22 0.9300 . ?
C23 F2A 1.228(7) . ?
C23 F3A 1.340(9) . ?
C23 F1A 1.377(7) . ?
F7 C27 1.335(2) . ?
F8 C27 1.317(2) . ?
F9 C27 1.302(2) . ?
O4 C26 1.253(2) . ?
O5 C26 1.226(2) . ?
C26 C27 1.541(2) . ?
F4 C25 1.316(2) . ?
F5 C25 1.341(2) . ?
F6 C25 1.324(2) . ?
O2 C24 1.234(2) . ?
O3 C24 1.226(3) . ?
C24 C25 1.535(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 H1 119.3(18) . . ?
C5 N1 C1 124.16(15) . . ?
C5 N1 H1 116.5(18) . . ?
C6 N2 H2 105.6(17) . . ?
C7 N2 C6 112.21(13) . . ?
C7 N2 C10 109.94(13) . . ?
C7 N2 H2 109.2(17) . . ?
C10 N2 C6 110.38(12) . . ?
C10 N2 H2 109.5(17) . . ?
C8 N3 C11 112.37(12) . . ?
C8 N3 H3 108.1(18) . . ?
C9 N3 C8 109.21(12) . . ?
C9 N3 C11 114.67(12) . . ?
C9 N3 H3 107.1(18) . . ?
C11 N3 H3 105.0(19) . . ?
O1 C1 N1 120.04(15) . . ?
O1 C1 C2 124.82(15) . . ?
N1 C1 C2 115.14(15) . . ?
C1 C2 H2A 119.7 . . ?
C3 C2 C1 120.61(15) . . ?
C3 C2 H2A 119.7 . . ?
C2 C3 H3A 119.2 . . ?
C2 C3 C4 121.57(15) . . ?
C4 C3 H3A 119.2 . . ?
C3 C4 C6 123.46(15) . . ?
C5 C4 C3 117.26(15) . . ?
C5 C4 C6 119.28(16) . . ?
N1 C5 C4 121.25(16) . . ?
N1 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
N2 C6 H6A 109.2 . . ?
N2 C6 H6B 109.2 . . ?
C4 C6 N2 112.17(13) . . ?
C4 C6 H6A 109.2 . . ?
C4 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
N2 C7 H7A 109.4 . . ?
N2 C7 H7B 109.4 . . ?
N2 C7 C8 110.96(13) . . ?
H7A C7 H7B 108.0 . . ?
C8 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
N3 C8 C7 110.59(13) . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
N3 C9 H9A 109.4 . . ?
N3 C9 H9B 109.4 . . ?
N3 C9 C10 111.10(14) . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
N2 C10 C9 111.22(13) . . ?
N2 C10 H10A 109.4 . . ?
N2 C10 H10B 109.4 . . ?
C9 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
N3 C11 H11 107.4 . . ?
N3 C11 C12 112.82(13) . . ?
C12 C11 H11 107.4 . . ?
C16 C11 N3 110.88(13) . . ?
C16 C11 H11 107.4 . . ?
C16 C11 C12 110.75(13) . . ?
C11 C12 H12A 109.8 . . ?
C11 C12 H12B 109.8 . . ?
C11 C12 C13 109.56(14) . . ?
H12A C12 H12B 108.2 . . ?
C13 C12 H12A 109.8 . . ?
C13 C12 H12B 109.8 . . ?
C12 C13 H13A 108.9 . . ?
C12 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 C12 113.35(14) . . ?
C14 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C13 C14 H14 106.6 . . ?
C13 C14 C15 108.73(14) . . ?
C15 C14 H14 106.6 . . ?
C17 C14 C13 115.23(14) . . ?
C17 C14 H14 106.6 . . ?
C17 C14 C15 112.61(15) . . ?
C14 C15 H15A 109.1 . . ?
C14 C15 H15B 109.1 . . ?
H15A C15 H15B 107.9 . . ?
C16 C15 C14 112.29(13) . . ?
C16 C15 H15A 109.1 . . ?
C16 C15 H15B 109.1 . . ?
C11 C16 C15 108.59(14) . . ?
C11 C16 H16A 110.0 . . ?
C11 C16 H16B 110.0 . . ?
C15 C16 H16A 110.0 . . ?
C15 C16 H16B 110.0 . . ?
H16A C16 H16B 108.4 . . ?
C18 C17 C14 122.98(16) . . ?
C18 C17 C22 117.08(17) . . ?
C22 C17 C14 119.79(16) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 C17 120.96(17) . . ?
C19 C18 H18 119.5 . . ?
C18 C19 C23 119.24(19) . . ?
C20 C19 C18 121.14(18) . . ?
C20 C19 C23 119.61(19) . . ?
C19 C20 H20 120.6 . . ?
C19 C20 C21 118.70(19) . . ?
C21 C20 H20 120.6 . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.3(2) . . ?
C22 C21 H21 119.8 . . ?
C17 C22 H22 119.1 . . ?
C21 C22 C17 121.81(19) . . ?
C21 C22 H22 119.1 . . ?
F1 C23 F2 102.9(3) . . ?
F1 C23 C19 111.1(3) . . ?
F2 C23 C19 112.1(3) . . ?
F3 C23 F1 109.1(4) . . ?
F3 C23 F2 108.3(5) . . ?
F3 C23 C19 112.9(4) . . ?
F2A C23 C19 116.8(4) . . ?
F2A C23 F3A 104.3(7) . . ?
F2A C23 F1A 104.9(6) . . ?
F3A C23 C19 114.0(5) . . ?
F3A C23 F1A 99.7(6) . . ?
F1A C23 C19 115.2(4) . . ?
O4 C26 C27 114.46(15) . . ?
O5 C26 O4 129.20(17) . . ?
O5 C26 C27 116.30(16) . . ?
F7 C27 C26 112.41(16) . . ?
F8 C27 F7 104.89(18) . . ?
F8 C27 C26 110.90(16) . . ?
F9 C27 F7 105.69(18) . . ?
F9 C27 F8 107.45(17) . . ?
F9 C27 C26 114.86(15) . . ?
O2 C24 C25 116.36(17) . . ?
O3 C24 O2 128.35(19) . . ?
O3 C24 C25 115.02(17) . . ?
F4 C25 F5 105.57(16) . . ?
F4 C25 F6 106.66(14) . . ?
F4 C25 C24 114.00(16) . . ?
F5 C25 C24 108.72(15) . . ?
F6 C25 F5 106.49(16) . . ?
F6 C25 C24 114.77(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 C2 C3 -179.33(17) . . . . ?
N1 C1 C2 C3 0.0(2) . . . . ?
N2 C7 C8 N3 58.77(18) . . . . ?
N3 C9 C10 N2 -57.06(18) . . . . ?
N3 C11 C12 C13 -176.83(13) . . . . ?
N3 C11 C16 C15 173.43(13) . . . . ?
C1 N1 C5 C4 1.1(3) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C2 C3 C4 C5 1.2(2) . . . . ?
C2 C3 C4 C6 -178.56(15) . . . . ?
C3 C4 C5 N1 -1.5(2) . . . . ?
C3 C4 C6 N2 89.22(19) . . . . ?
C5 N1 C1 O1 179.03(16) . . . . ?
C5 N1 C1 C2 -0.3(2) . . . . ?
C5 C4 C6 N2 -90.51(19) . . . . ?
C6 N2 C7 C8 179.70(13) . . . . ?
C6 N2 C10 C9 -179.57(14) . . . . ?
C6 C4 C5 N1 178.25(15) . . . . ?
C7 N2 C6 C4 -64.73(18) . . . . ?
C7 N2 C10 C9 56.11(18) . . . . ?
C8 N3 C9 C10 57.23(17) . . . . ?
C8 N3 C11 C12 70.17(17) . . . . ?
C8 N3 C11 C16 -164.96(13) . . . . ?
C9 N3 C8 C7 -58.02(17) . . . . ?
C9 N3 C11 C12 -55.32(18) . . . . ?
C9 N3 C11 C16 69.56(17) . . . . ?
C10 N2 C6 C4 172.27(14) . . . . ?
C10 N2 C7 C8 -57.05(18) . . . . ?
C11 N3 C8 C7 173.57(13) . . . . ?
C11 N3 C9 C10 -175.65(13) . . . . ?
C11 C12 C13 C14 -55.38(19) . . . . ?
C12 C11 C16 C15 -60.53(18) . . . . ?
C12 C13 C14 C15 53.42(19) . . . . ?
C12 C13 C14 C17 -74.06(18) . . . . ?
C13 C14 C15 C16 -55.75(19) . . . . ?
C13 C14 C17 C18 -8.8(2) . . . . ?
C13 C14 C17 C22 175.83(16) . . . . ?
C14 C15 C16 C11 59.85(19) . . . . ?
C14 C17 C18 C19 -175.48(16) . . . . ?
C14 C17 C22 C21 175.46(19) . . . . ?
C15 C14 C17 C18 -134.29(17) . . . . ?
C15 C14 C17 C22 50.3(2) . . . . ?
C16 C11 C12 C13 58.22(18) . . . . ?
C17 C14 C15 C16 73.20(19) . . . . ?
C17 C18 C19 C20 0.3(3) . . . . ?
C17 C18 C19 C23 -179.11(16) . . . . ?
C18 C17 C22 C21 -0.2(3) . . . . ?
C18 C19 C20 C21 -0.4(3) . . . . ?
C18 C19 C23 F1 -140.6(5) . . . . ?
C18 C19 C23 F2 -26.1(4) . . . . ?
C18 C19 C23 F3 96.5(6) . . . . ?
C18 C19 C23 F2A -57.5(10) . . . . ?
C18 C19 C23 F3A 64.4(8) . . . . ?
C18 C19 C23 F1A 178.9(10) . . . . ?
C19 C20 C21 C22 0.3(4) . . . . ?
C20 C19 C23 F1 40.0(5) . . . . ?
C20 C19 C23 F2 154.5(4) . . . . ?
C20 C19 C23 F3 -82.9(6) . . . . ?
C20 C19 C23 F2A 123.1(10) . . . . ?
C20 C19 C23 F3A -115.0(8) . . . . ?
C20 C19 C23 F1A -0.5(10) . . . . ?
C20 C21 C22 C17 0.0(4) . . . . ?
C22 C17 C18 C19 0.0(3) . . . . ?
C23 C19 C20 C21 179.0(2) . . . . ?
O4 C26 C27 F7 46.0(2) . . . . ?
O4 C26 C27 F8 -71.0(2) . . . . ?
O4 C26 C27 F9 166.94(17) . . . . ?
O5 C26 C27 F7 -136.06(19) . . . . ?
O5 C26 C27 F8 106.9(2) . . . . ?
O5 C26 C27 F9 -15.2(3) . . . . ?
O2 C24 C25 F4 -160.93(17) . . . . ?
O2 C24 C25 F5 81.6(2) . . . . ?
O2 C24 C25 F6 -37.5(2) . . . . ?
O3 C24 C25 F4 24.6(3) . . . . ?
O3 C24 C25 F5 -92.9(2) . . . . ?
O3 C24 C25 F6 148.04(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Vapour deposition'
_chemical_compound_source        synthesis
####################################################################### 
# 
# 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_19jlr004
_database_code_depnum_ccdc_archive 'CCDC 1997202'
loop_
_audit_author_name
_audit_author_address
'Jurg Hauser'
;Department of Chemistry and Biochemistry, University of Bern
Switzerland
;
_audit_update_record             
;
2020-04-15 deposited with the CCDC.	2020-06-25 downloaded from the CCDC.
;
_audit_creation_date             2019-04-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            19
_chemical_name_systematic        
5-(4-((1s,4s)-4-(tert-butyl)cyclohexyl)piperazine-1-carbonyl)pyridin-2(1H)-one
_chemical_formula_moiety         'C20 H32 N3 O2, C2 F3 O2, 1.65(H2 O)'
_chemical_formula_sum            'C22 H35.31 F3 N3 O5.65'
_chemical_formula_weight         489.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H35 F3 N3 O5.5'
_chemical_oxdiff_usercomment     MRC92F1TFA
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'
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           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   17.41370(10)
_cell_length_b                   8.14510(10)
_cell_length_c                   33.6364(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.4130(10)
_cell_angle_gamma                90
_cell_volume                     4770.74(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    16683
_cell_measurement_temperature    173.01(10)
_cell_measurement_theta_max      76.6160
_cell_measurement_theta_min      2.8610
_shelx_estimated_absorpt_T_max   0.939
_shelx_estimated_absorpt_T_min   0.828
_exptl_absorpt_coefficient_mu    0.961
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.643
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.39a (Rigaku Oxford Diffraction, 2019)
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             2084
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0332
0 0 1 0.0332
-1 1 -1 0.0595
1 -1 1 0.0505
3 3 -5 0.0663
-3 -3 5 0.0663
-1 0 0 0.1012
1 0 0 0.1012
1 1 1 0.0602
-1 -1 -1 0.0602

_exptl_crystal_size_max          0.204
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.066
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            23932
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.093
_diffrn_reflns_theta_min         2.627
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -56.00   6.00   0.50    0.35    --  -18.75 106.00-149.00  124
  2  ω     17.00  86.00   0.50    0.35    --   47.95-106.00 111.00  138
  3  ω     35.00 111.00   0.50    1.39    --  107.11-106.00 111.00  152
  4  ω    102.00 174.00   0.50    1.39    --  107.11 106.00-149.00  144
  5  ω    -27.00  56.00   0.50    0.35    --  -18.75  15.00 -30.00  166
  6  ω    -66.00  -9.00   0.50    0.35    --  -18.75 125.00  30.00  114
  7  ω    -26.00  23.00   0.50    0.35    --   47.95 -19.00 120.00   98
  8  ω    -26.00  23.00   0.50    0.35    --   47.95 -19.00 -30.00   98
  9  ω    -26.00  23.00   0.50    0.35    --   47.95 -19.00-150.00   98
 10  ω    -26.00  23.00   0.50    0.35    --   47.95 -19.00   0.00   98
 11  ω     35.00  68.00   0.50    1.39    --  107.11 -61.00 120.00   66
 12  ω     35.00  68.00   0.50    1.39    --  107.11 -61.00 -60.00   66
 13  ω     95.00 174.00   0.50    1.39    --  107.11  45.00-180.00  158
 14  ω     35.00 117.00   0.50    1.39    --  107.11-125.00 -60.00  164
 15  ω     35.00  68.00   0.50    1.39    --  107.11 -61.00  90.00   66
 16  ω     95.00 174.00   0.50    1.39    --  107.11  30.00-150.00  158
 17  ω     92.00 174.00   0.50    1.39    --  107.11 125.00 -90.00  164
 18  ω     35.00  68.00   0.50    1.39    --  107.11 -61.00  30.00   66
 19  ω     35.00  68.00   0.50    1.39    --  107.11 -61.00   0.00   66
 20  ω     35.00 117.00   0.50    1.39    --  107.11-125.00-150.00  164
 21  ω     35.00 102.00   0.50    1.39    --  107.11 -77.00-120.00  134
 22  ω     35.00  68.00   0.50    1.39    --  107.11 -61.00-150.00   66
 23  ω     35.00 102.00   0.50    1.39    --  107.11 -77.00 -30.00  134
 24  ω     35.00  68.00   0.50    1.39    --  107.11 -61.00 -30.00   66
 25  ω     26.00  80.00   0.50    0.35    --   47.95  77.00 120.00  108
 26  ω     26.00 120.00   0.50    0.35    --   47.95  77.00 -30.00  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0213904000
_diffrn_orient_matrix_UB_12      0.1731522000
_diffrn_orient_matrix_UB_13      -0.0146535000
_diffrn_orient_matrix_UB_21      -0.0066406000
_diffrn_orient_matrix_UB_22      -0.0591697000
_diffrn_orient_matrix_UB_23      -0.0433942000
_diffrn_orient_matrix_UB_31      -0.0855817000
_diffrn_orient_matrix_UB_32      0.0478522000
_diffrn_orient_matrix_UB_33      -0.0006366000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4477
_reflns_number_total             4918
_reflns_odcompleteness_completeness 99.89
_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 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         4918
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0362
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0478P)²+2.9531P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.0974
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Others
 Sof(O6A)=Sof(H6AA)=Sof(H6AB)=FVAR(1)
 Sof(O6B)=Sof(H6BA)=Sof(H6BB)=FVAR(2)
 Sof(F2A)=Sof(F1A)=Sof(F3A)=1-FVAR(3)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(3)
3.a Free rotating group:
 O6A(H6AA,H6AB), O6B(H6BA,H6BB), O5(H5A,H5B)
3.b Ternary CH refined with riding coordinates:
 N3(H3), C11(H11), C14(H14)
3.c Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C12(H12A,H12B),
 C13(H13A,H13B), C15(H15A,H15B), C16(H16A,H16B)
3.d Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3A), C5(H5)
3.e Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.21205(7) 0.78237(15) 0.55722(3) 0.0564(3) Uani 1 1 d . . . . .
O2 O 0.44797(6) 0.24977(12) 0.50248(3) 0.0419(2) Uani 1 1 d . . . . .
N1 N 0.24245(6) 0.51164(15) 0.55974(3) 0.0369(3) Uani 1 1 d . . . . .
H1 H 0.195763 0.489895 0.568082 0.044 Uiso 1 1 calc R . . . .
N2 N 0.43230(5) 0.16564(12) 0.56573(3) 0.0264(2) Uani 1 1 d . . . . .
N3 N 0.54938(5) 0.05992(11) 0.62239(3) 0.0252(2) Uani 1 1 d . . . . .
H3 H 0.521027 -0.033551 0.634781 0.030 Uiso 1 1 calc R . . . .
C1 C 0.26008(7) 0.67260(18) 0.55120(4) 0.0371(3) Uani 1 1 d . . . . .
C2 C 0.33488(7) 0.69652(16) 0.53476(4) 0.0346(3) Uani 1 1 d . . . . .
H2 H 0.350128 0.803676 0.526940 0.042 Uiso 1 1 calc R . . . .
C3 C 0.38441(6) 0.56970(15) 0.53010(3) 0.0290(2) Uani 1 1 d . . . . .
H3A H 0.433266 0.589069 0.518613 0.035 Uiso 1 1 calc R . . . .
C4 C 0.36438(6) 0.40880(14) 0.54210(3) 0.0252(2) Uani 1 1 d . . . . .
C5 C 0.29215(6) 0.38436(16) 0.55618(4) 0.0312(3) Uani 1 1 d . . . . .
H5 H 0.276401 0.277019 0.563576 0.037 Uiso 1 1 calc R . . . .
C6 C 0.41828(6) 0.26979(14) 0.53545(3) 0.0265(2) Uani 1 1 d . . . . .
C7 C 0.42427(6) 0.20461(14) 0.60785(3) 0.0271(2) Uani 1 1 d . . . . .
H7A H 0.392832 0.119159 0.620897 0.032 Uiso 1 1 calc R . . . .
H7B H 0.397520 0.311150 0.610745 0.032 Uiso 1 1 calc R . . . .
C8 C 0.50279(7) 0.21379(14) 0.62801(3) 0.0279(2) Uani 1 1 d . . . . .
H8A H 0.531494 0.308258 0.617059 0.033 Uiso 1 1 calc R . . . .
H8B H 0.495771 0.233230 0.656807 0.033 Uiso 1 1 calc R . . . .
C9 C 0.55563(7) 0.02716(15) 0.57847(4) 0.0300(2) Uani 1 1 d . . . . .
H9A H 0.583727 -0.076919 0.574158 0.036 Uiso 1 1 calc R . . . .
H9B H 0.584989 0.116757 0.565746 0.036 Uiso 1 1 calc R . . . .
C10 C 0.47660(7) 0.01574(14) 0.55958(3) 0.0295(2) Uani 1 1 d . . . . .
H10A H 0.481931 -0.004325 0.530705 0.035 Uiso 1 1 calc R . . . .
H10B H 0.448648 -0.078434 0.571171 0.035 Uiso 1 1 calc R . . . .
C11 C 0.62832(6) 0.07307(14) 0.64250(4) 0.0313(3) Uani 1 1 d . . . . .
H11 H 0.655405 0.170262 0.631055 0.038 Uiso 1 1 calc R . . . .
C12 C 0.62188(7) 0.09876(15) 0.68728(4) 0.0346(3) Uani 1 1 d . . . . .
H12A H 0.585704 0.190129 0.692244 0.041 Uiso 1 1 calc R . . . .
H12B H 0.672745 0.131904 0.697879 0.041 Uiso 1 1 calc R . . . .
C13 C 0.59450(7) -0.05277(14) 0.71002(4) 0.0287(2) Uani 1 1 d . . . . .
H13A H 0.541126 -0.078709 0.701862 0.034 Uiso 1 1 calc R . . . .
H13B H 0.594468 -0.028194 0.738843 0.034 Uiso 1 1 calc R . . . .
C14 C 0.64566(6) -0.20270(14) 0.70240(3) 0.0249(2) Uani 1 1 d . . . . .
H14 H 0.698605 -0.171574 0.711303 0.030 Uiso 1 1 calc R . . . .
C15 C 0.64990(6) -0.23143(14) 0.65734(3) 0.0276(2) Uani 1 1 d . . . . .
H15A H 0.685295 -0.323815 0.651993 0.033 Uiso 1 1 calc R . . . .
H15B H 0.598395 -0.262356 0.647182 0.033 Uiso 1 1 calc R . . . .
C16 C 0.67784(7) -0.07852(16) 0.63520(4) 0.0338(3) Uani 1 1 d . . . . .
H16A H 0.731250 -0.054350 0.643622 0.041 Uiso 1 1 calc R . . . .
H16B H 0.678337 -0.102142 0.606335 0.041 Uiso 1 1 calc R . . . .
C17 C 0.62330(6) -0.35829(14) 0.72658(3) 0.0261(2) Uani 1 1 d . . . . .
C18 C 0.61708(7) -0.31775(17) 0.77101(4) 0.0347(3) Uani 1 1 d . . . . .
H18A H 0.664134 -0.262618 0.779974 0.052 Uiso 1 1 calc GR . . . .
H18B H 0.610158 -0.419455 0.786133 0.052 Uiso 1 1 calc GR . . . .
H18C H 0.572974 -0.245302 0.775287 0.052 Uiso 1 1 calc GR . . . .
C19 C 0.68571(7) -0.48961(15) 0.72199(4) 0.0318(3) Uani 1 1 d . . . . .
H19A H 0.687227 -0.526450 0.694269 0.048 Uiso 1 1 calc GR . . . .
H19B H 0.674129 -0.583126 0.739268 0.048 Uiso 1 1 calc GR . . . .
H19C H 0.735672 -0.443177 0.729493 0.048 Uiso 1 1 calc GR . . . .
C20 C 0.54664(7) -0.43156(16) 0.71272(4) 0.0350(3) Uani 1 1 d . . . . .
H20A H 0.505718 -0.350332 0.716217 0.053 Uiso 1 1 calc GR . . . .
H20B H 0.535143 -0.529538 0.728510 0.053 Uiso 1 1 calc GR . . . .
H20C H 0.549999 -0.461676 0.684584 0.053 Uiso 1 1 calc GR . . . .
F1 F 0.2915(2) -0.2727(7) 0.64558(16) 0.0642(12) Uani 0.588(18) 1 d . . . A 1
F2 F 0.3334(3) -0.5088(6) 0.6557(2) 0.0656(14) Uani 0.588(18) 1 d . . . A 1
F3 F 0.3495(3) -0.3240(8) 0.69928(12) 0.0519(11) Uani 0.588(18) 1 d . . . A 1
O3 O 0.44285(5) -0.15146(11) 0.64913(3) 0.0363(2) Uani 1 1 d . . . . .
O4 O 0.45846(5) -0.39705(11) 0.61941(3) 0.0337(2) Uani 1 1 d . . . . .
C21 C 0.42598(6) -0.29608(14) 0.64084(3) 0.0247(2) Uani 1 1 d . . . . .
C22 C 0.35127(6) -0.35386(14) 0.66109(4) 0.0273(2) Uani 1 1 d . . . . .
O6A O 0.250000 0.0532(3) 0.500000 0.0845(15) Uani 0.704(7) 2 d S T P B 1
H6AA H 0.255740 -0.018269 0.481840 0.127 Uiso 0.352(4) 1 d G . . B 1
H6AB H 0.295500 0.078435 0.507031 0.127 Uiso 0.352(4) 1 d G . . B 1
O6B O 0.2093(3) 0.0719(5) 0.53436(14) 0.0626(16) Uani 0.301(4) 1 d . . . C 2
H6BA H 0.183292 -0.009230 0.525748 0.094 Uiso 0.301(4) 1 d G . . C 2
H6BB H 0.249669 0.037091 0.545980 0.094 Uiso 0.301(4) 1 d G . . C 2
O5 O 0.58801(5) -0.40754(16) 0.56962(3) 0.0486(3) Uani 1 1 d . . . . .
H5A H 0.548954 -0.398568 0.584331 0.073 Uiso 1 1 d G . . . .
H5B H 0.574128 -0.365647 0.547560 0.073 Uiso 1 1 d G . . . .
F2A F 0.3545(8) -0.5149(8) 0.6670(4) 0.078(3) Uani 0.412(18) 1 d . . . A 2
F1A F 0.2911(4) -0.319(2) 0.6415(2) 0.089(2) Uani 0.412(18) 1 d . . . A 2
F3A F 0.3434(5) -0.2949(13) 0.6969(2) 0.071(2) Uani 0.412(18) 1 d . . . A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2420(16) . ?
O2 C6 1.2378(14) . ?
N1 H1 0.8800 . ?
N1 C1 1.377(2) . ?
N1 C5 1.3563(16) . ?
N2 C6 1.3466(15) . ?
N2 C7 1.4597(14) . ?
N2 C10 1.4597(14) . ?
N3 H3 1.0000 . ?
N3 C8 1.5055(14) . ?
N3 C9 1.5061(15) . ?
N3 C11 1.5314(14) . ?
C1 C2 1.432(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.3555(17) . ?
C3 H3A 0.9500 . ?
C3 C4 1.4157(17) . ?
C4 C5 1.3618(16) . ?
C4 C6 1.4886(15) . ?
C5 H5 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.5238(16) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5143(16) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11 1.0000 . ?
C11 C12 1.5255(18) . ?
C11 C16 1.5270(17) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.5300(17) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.5343(15) . ?
C14 H14 1.0000 . ?
C14 C15 1.5360(15) . ?
C14 C17 1.5568(16) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.5321(16) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.5351(16) . ?
C17 C19 1.5335(16) . ?
C17 C20 1.5319(15) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
F1 C22 1.335(4) . ?
F2 C22 1.312(5) . ?
F3 C22 1.308(4) . ?
O3 C21 1.2452(14) . ?
O4 C21 1.2336(15) . ?
C21 C22 1.5462(15) . ?
C22 F2A 1.328(7) . ?
C22 F1A 1.266(6) . ?
C22 F3A 1.305(7) . ?
O6A H6AA 0.8504 . ?
O6A H6AA 0.85(9) 2_556 ?
O6A H6AB 0.8504 . ?
O6A H6AB 0.85(4) 2_556 ?
O6B H6BA 0.8506 . ?
O6B H6BB 0.8504 . ?
O5 H5A 0.8471 . ?
O5 H5B 0.8502 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 H1 117.8 . . ?
C5 N1 H1 117.8 . . ?
C5 N1 C1 124.46(11) . . ?
C6 N2 C7 125.39(10) . . ?
C6 N2 C10 120.86(9) . . ?
C7 N2 C10 111.95(9) . . ?
C8 N3 H3 108.3 . . ?
C8 N3 C9 108.27(8) . . ?
C8 N3 C11 111.66(9) . . ?
C9 N3 H3 108.3 . . ?
C9 N3 C11 112.00(9) . . ?
C11 N3 H3 108.3 . . ?
O1 C1 N1 120.00(14) . . ?
O1 C1 C2 125.49(15) . . ?
N1 C1 C2 114.50(11) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 C1 121.49(12) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 H3A 119.5 . . ?
C2 C3 C4 120.93(11) . . ?
C4 C3 H3A 119.5 . . ?
C3 C4 C6 120.28(10) . . ?
C5 C4 C3 117.69(11) . . ?
C5 C4 C6 121.73(11) . . ?
N1 C5 C4 120.70(12) . . ?
N1 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
O2 C6 N2 121.33(11) . . ?
O2 C6 C4 120.19(10) . . ?
N2 C6 C4 118.47(10) . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
N2 C7 C8 110.52(9) . . ?
H7A C7 H7B 108.1 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
N3 C8 C7 112.70(9) . . ?
N3 C8 H8A 109.1 . . ?
N3 C8 H8B 109.1 . . ?
C7 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
N3 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
N3 C9 C10 110.51(9) . . ?
H9A C9 H9B 108.1 . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
N2 C10 C9 111.64(9) . . ?
N2 C10 H10A 109.3 . . ?
N2 C10 H10B 109.3 . . ?
C9 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
N3 C11 H11 108.0 . . ?
C12 C11 N3 111.93(10) . . ?
C12 C11 H11 108.0 . . ?
C12 C11 C16 108.37(10) . . ?
C16 C11 N3 112.25(10) . . ?
C16 C11 H11 108.0 . . ?
C11 C12 H12A 108.7 . . ?
C11 C12 H12B 108.7 . . ?
C11 C12 C13 114.10(10) . . ?
H12A C12 H12B 107.6 . . ?
C13 C12 H12A 108.7 . . ?
C13 C12 H12B 108.7 . . ?
C12 C13 H13A 109.2 . . ?
C12 C13 H13B 109.2 . . ?
C12 C13 C14 112.03(10) . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
C13 C14 H14 106.5 . . ?
C13 C14 C15 108.55(9) . . ?
C13 C14 C17 114.39(9) . . ?
C15 C14 H14 106.5 . . ?
C15 C14 C17 113.93(9) . . ?
C17 C14 H14 106.5 . . ?
C14 C15 H15A 109.2 . . ?
C14 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C16 C15 C14 111.92(10) . . ?
C16 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
C11 C16 C15 113.42(10) . . ?
C11 C16 H16A 108.9 . . ?
C11 C16 H16B 108.9 . . ?
C15 C16 H16A 108.9 . . ?
C15 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C18 C17 C14 110.68(10) . . ?
C19 C17 C14 109.58(9) . . ?
C19 C17 C18 107.65(9) . . ?
C20 C17 C14 112.26(9) . . ?
C20 C17 C18 108.21(10) . . ?
C20 C17 C19 108.32(10) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O3 C21 C22 112.77(10) . . ?
O4 C21 O3 130.78(11) . . ?
O4 C21 C22 116.44(10) . . ?
F1 C22 C21 109.4(2) . . ?
F2 C22 F1 103.8(4) . . ?
F2 C22 C21 115.5(2) . . ?
F3 C22 F1 105.6(3) . . ?
F3 C22 F2 107.9(4) . . ?
F3 C22 C21 113.7(2) . . ?
F2A C22 C21 109.4(4) . . ?
F1A C22 C21 113.5(3) . . ?
F1A C22 F2A 109.4(5) . . ?
F1A C22 F3A 107.9(5) . . ?
F3A C22 C21 112.9(4) . . ?
F3A C22 F2A 103.2(6) . . ?
H6AA O6A H6AA 93.5 . 2_556 ?
H6AA O6A H6AB 104.5 2_556 2_556 ?
H6AA O6A H6AB 94.6 . 2_556 ?
H6AA O6A H6AB 104.5 . . ?
H6AB O6A H6AA 94.6 . 2_556 ?
H6AB O6A H6AB 152.1 . 2_556 ?
H6AA O6B H6AB 64.0 2_556 2_556 ?
H6BA O6B H6BB 109.5 . . ?
H5A O5 H5B 104.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Vapour deposition'
_chemical_compound_source        synthesis
####################################################################### 
# 
# 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_18jlr007
_database_code_depnum_ccdc_archive 'CCDC 1997204'
loop_
_audit_author_name
_audit_author_address
'Michal Andrzejewski'
;Department of Chemistry and Biochemistry, University of Bern
Switzerland
;
_audit_update_record             
;
2020-04-15 deposited with the CCDC.	2020-06-25 downloaded from the CCDC.
;
_audit_creation_date             2018-04-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            cis-22a
_chemical_name_systematic        
1-(pyridin-3-yl)-4-((1s,4s)-4-(m-tolyl)cyclohexyl)piperazine
_chemical_formula_moiety         'C22 H29 N3'
_chemical_formula_sum            'C22 H29 N3'
_chemical_formula_weight         335.48
_chemical_melting_point          ?
_chemical_oxdiff_formula         C22H29N3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   7.2232(3)
_cell_length_b                   8.9059(4)
_cell_length_c                   15.2815(6)
_cell_angle_alpha                96.464(3)
_cell_angle_beta                 95.779(3)
_cell_angle_gamma                99.987(4)
_cell_volume                     954.71(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6144
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      27.7240
_cell_measurement_theta_min      2.3300
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68722
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.925
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16139
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.104
_diffrn_reflns_theta_min         2.343
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0965
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -49.00  65.00   1.00    6.50    --   27.42 -57.00 -30.00  114
  2  ω    -54.00  83.00   1.00    6.50    --   27.42 -38.00  90.00  137
  3  ω     35.00 122.00   1.00    6.50    --   27.42 178.00 -60.00   87
  4  ω    -57.00  71.00   1.00    6.50    --   27.42 -77.00  30.00  128
  5  ω    -57.00  71.00   1.00    6.50    --   27.42 -77.00 -90.00  128
  6  ω    -20.00  32.00   1.00    6.50    --  -23.50 -99.00   0.00   52
  7  ω    -20.00  32.00   1.00    6.50    --  -23.50 -99.00-180.00   52
  8  ω    -10.00 103.00   1.00    6.50    --   27.42  57.00 120.00  113
  9  ω    -10.00 103.00   1.00    6.50    --   27.42  57.00-120.00  113
 10  ω    -10.00  72.00   1.00    6.50    --   27.42  57.00  30.00   82
 11  ω    -10.00 103.00   1.00    6.50    --   27.42  57.00 -30.00  113
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0638578000
_diffrn_orient_matrix_UB_12      -0.0098142000
_diffrn_orient_matrix_UB_13      0.0321513000
_diffrn_orient_matrix_UB_21      -0.0468843000
_diffrn_orient_matrix_UB_22      0.0567973000
_diffrn_orient_matrix_UB_23      -0.0162645000
_diffrn_orient_matrix_UB_31      -0.0617854000
_diffrn_orient_matrix_UB_32      -0.0577471000
_diffrn_orient_matrix_UB_33      -0.0302867000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3364
_reflns_number_total             4310
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4310
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0504
_refine_ls_restrained_S_all      1.051
_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)+(0.0590P)²+0.2372P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1229
_refine_ls_wR_factor_ref         0.1388
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H14A-H9A
 2.01 with sigma of 0.001
 H12B-H6
 2.01 with sigma of 0.001
 H8A-H4
 2.01 with sigma of 0.001
3.a Ternary CH refined with riding coordinates:
 C16(H16), C13(H13)
3.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C17(H17A,H17B), C18(H18A,H18B), C14(H14A,H14B), C8(H8A,H8B),
 C9(H9A,H9B), C11(H11A,H11B), C12(H12A,H12B)
3.c Aromatic/amide H refined with riding coordinates:
 C24(H24), C20(H20), C22(H22), C23(H23), C4(H4), C6(H6), C2(H2), C3(H3)
3.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N10 N 0.49313(15) 0.37955(13) 0.81627(7) 0.0298(3) Uani 1 1 d . . . . .
N7 N 0.40600(16) 0.56760(13) 0.68052(7) 0.0324(3) Uani 1 1 d . . . . .
C19 C 0.86717(18) -0.00768(15) 0.84249(9) 0.0284(3) Uani 1 1 d . . . . .
C16 C 0.74627(18) 0.08820(15) 0.89094(9) 0.0300(3) Uani 1 1 d . . . . .
H16 H 0.7436 0.0577 0.9505 0.036 Uiso 1 1 calc R . . . .
C15 C 0.82789(18) 0.26131(15) 0.90234(9) 0.0310(3) Uani 1 1 d . . . . .
H15A H 0.9543 0.2811 0.9345 0.037 Uiso 1 1 calc R . . . .
H15B H 0.8368 0.2952 0.8445 0.037 Uiso 1 1 calc R . . . .
N1 N 0.2068(2) 0.64384(18) 0.46165(9) 0.0549(4) Uani 1 1 d . . . . .
C24 C 0.93909(19) -0.12259(15) 0.88156(9) 0.0327(3) Uani 1 1 d . . . . .
H24 H 0.9138 -0.1401 0.9384 0.039 Uiso 1 1 calc R . . . .
C17 C 0.54037(19) 0.05601(16) 0.84606(10) 0.0328(3) Uani 1 1 d . . . . .
H17A H 0.5386 0.0791 0.7855 0.039 Uiso 1 1 calc R . . . .
H17B H 0.4872 -0.0523 0.8441 0.039 Uiso 1 1 calc R . . . .
C20 C 0.90890(19) 0.01551(16) 0.75723(9) 0.0324(3) Uani 1 1 d . . . . .
H20 H 0.8614 0.0917 0.7302 0.039 Uiso 1 1 calc R . . . .
C13 C 0.4989(2) 0.32529(16) 0.90418(9) 0.0331(3) Uani 1 1 d . . . . .
H13 H 0.4218 0.3808 0.9406 0.040 Uiso 1 1 calc R . . . .
C18 C 0.4187(2) 0.15238(16) 0.89573(10) 0.0353(3) Uani 1 1 d . . . . .
H18A H 0.4112 0.1224 0.9545 0.042 Uiso 1 1 calc R . . . .
H18B H 0.2913 0.1317 0.8645 0.042 Uiso 1 1 calc R . . . .
C14 C 0.7013(2) 0.35130(16) 0.95316(8) 0.0344(3) Uani 1 1 d . . . . .
H14A H 0.7558 0.4601 0.9607 0.041 Uiso 1 1 calc DR . . . .
H14B H 0.6961 0.3194 1.0116 0.041 Uiso 1 1 calc R . . . .
C5 C 0.3933(2) 0.62808(16) 0.60012(9) 0.0332(3) Uani 1 1 d . . . . .
C8 C 0.5966(2) 0.58572(16) 0.72854(8) 0.0351(3) Uani 1 1 d . . . . .
H8A H 0.6589 0.6925 0.7337 0.042 Uiso 1 1 calc DR . . . .
H8B H 0.6702 0.5242 0.6948 0.042 Uiso 1 1 calc R . . . .
C9 C 0.5927(2) 0.53841(15) 0.81861(8) 0.0360(3) Uani 1 1 d . . . . .
H9A H 0.7216 0.5483 0.8466 0.043 Uiso 1 1 calc DR . . . .
H9B H 0.5306 0.6069 0.8543 0.043 Uiso 1 1 calc R . . . .
C11 C 0.29851(19) 0.37480(17) 0.77716(10) 0.0365(3) Uani 1 1 d . . . . .
H11A H 0.2415 0.4457 0.8140 0.044 Uiso 1 1 calc R . . . .
H11B H 0.2256 0.2722 0.7761 0.044 Uiso 1 1 calc R . . . .
C12 C 0.2896(2) 0.41657(17) 0.68463(8) 0.0379(3) Uani 1 1 d . . . . .
H12A H 0.3329 0.3388 0.6463 0.045 Uiso 1 1 calc R . . . .
H12B H 0.1591 0.4176 0.6627 0.045 Uiso 1 1 calc DR . . . .
C22 C 1.0882(2) -0.18635(17) 0.75248(10) 0.0405(4) Uani 1 1 d . . . . .
H22 H 1.1617 -0.2465 0.7230 0.049 Uiso 1 1 calc R . . . .
C21 C 1.0194(2) -0.07190(17) 0.71140(10) 0.0377(3) Uani 1 1 d . . . . .
C23 C 1.0482(2) -0.21124(17) 0.83646(10) 0.0386(3) Uani 1 1 d . . . . .
H23 H 1.0948 -0.2882 0.8632 0.046 Uiso 1 1 calc R . . . .
C4 C 0.5339(2) 0.74190(19) 0.57868(9) 0.0454(4) Uani 1 1 d . . . . .
H4 H 0.6457 0.7755 0.6169 0.054 Uiso 1 1 calc DR . . . .
C6 C 0.2327(2) 0.58357(19) 0.53663(9) 0.0465(4) Uani 1 1 d . . . . .
H6 H 0.1374 0.5062 0.5479 0.056 Uiso 1 1 calc DR . . . .
C2 C 0.3434(3) 0.7529(2) 0.44491(11) 0.0506(4) Uani 1 1 d . . . . .
H2 H 0.3273 0.7963 0.3927 0.061 Uiso 1 1 calc R . . . .
C3 C 0.5071(3) 0.8041(2) 0.50151(11) 0.0508(4) Uani 1 1 d . . . . .
H3 H 0.5999 0.8809 0.4876 0.061 Uiso 1 1 calc R . . . .
C25 C 1.0640(3) -0.0419(2) 0.61977(12) 0.0564(5) Uani 1 1 d . . . . .
H25A H 1.0095 -0.1309 0.5778 0.085 Uiso 1 1 calc GR . . . .
H25B H 1.1988 -0.0207 0.6194 0.085 Uiso 1 1 calc GR . . . .
H25C H 1.0120 0.0448 0.6039 0.085 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N10 C13 1.4772(17) . ?
N10 C9 1.4665(17) . ?
N10 C11 1.4627(17) . ?
N7 C5 1.3970(18) . ?
N7 C8 1.4676(17) . ?
N7 C12 1.4688(17) . ?
C19 C16 1.5121(18) . ?
C19 C24 1.3904(19) . ?
C19 C20 1.3960(18) . ?
C16 H16 0.9800 . ?
C16 C15 1.5357(18) . ?
C16 C17 1.5385(18) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C14 1.5293(18) . ?
N1 C6 1.3289(18) . ?
N1 C2 1.325(2) . ?
C24 H24 0.9300 . ?
C24 C23 1.386(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.5280(19) . ?
C20 H20 0.9300 . ?
C20 C21 1.3926(19) . ?
C13 H13 0.9800 . ?
C13 C18 1.534(2) . ?
C13 C14 1.5405(19) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C5 C4 1.397(2) . ?
C5 C6 1.404(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.4857(16) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.5001(18) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C22 H22 0.9300 . ?
C22 C21 1.391(2) . ?
C22 C23 1.377(2) . ?
C21 C25 1.510(2) . ?
C23 H23 0.9300 . ?
C4 H4 0.9300 . ?
C4 C3 1.369(2) . ?
C6 H6 0.9300 . ?
C2 H2 0.9300 . ?
C2 C3 1.369(2) . ?
C3 H3 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

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
C9 N10 C13 113.53(10) . . ?
C11 N10 C13 111.51(11) . . ?
C11 N10 C9 106.19(10) . . ?
C5 N7 C8 116.43(11) . . ?
C5 N7 C12 117.91(11) . . ?
C8 N7 C12 112.37(10) . . ?
C24 C19 C16 120.77(12) . . ?
C24 C19 C20 118.02(13) . . ?
C20 C19 C16 121.21(12) . . ?
C19 C16 H16 107.2 . . ?
C19 C16 C15 112.88(11) . . ?
C19 C16 C17 111.79(11) . . ?
C15 C16 H16 107.2 . . ?
C15 C16 C17 110.30(11) . . ?
C17 C16 H16 107.2 . . ?
C16 C15 H15A 109.6 . . ?
C16 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
C14 C15 C16 110.27(11) . . ?
C14 C15 H15A 109.6 . . ?
C14 C15 H15B 109.6 . . ?
C2 N1 C6 117.72(15) . . ?
C19 C24 H24 119.7 . . ?
C23 C24 C19 120.53(13) . . ?
C23 C24 H24 119.7 . . ?
C16 C17 H17A 109.3 . . ?
C16 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
C18 C17 C16 111.52(11) . . ?
C18 C17 H17A 109.3 . . ?
C18 C17 H17B 109.3 . . ?
C19 C20 H20 119.0 . . ?
C21 C20 C19 122.08(13) . . ?
C21 C20 H20 119.0 . . ?
N10 C13 H13 108.6 . . ?
N10 C13 C18 111.04(11) . . ?
N10 C13 C14 112.76(11) . . ?
C18 C13 H13 108.6 . . ?
C18 C13 C14 107.00(11) . . ?
C14 C13 H13 108.6 . . ?
C17 C18 C13 112.09(11) . . ?
C17 C18 H18A 109.2 . . ?
C17 C18 H18B 109.2 . . ?
C13 C18 H18A 109.2 . . ?
C13 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C15 C14 C13 111.66(10) . . ?
C15 C14 H14A 109.3 . . ?
C15 C14 H14B 109.3 . . ?
C13 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 107.9 . . ?
N7 C5 C4 122.87(12) . . ?
N7 C5 C6 121.98(13) . . ?
C4 C5 C6 115.08(12) . . ?
N7 C8 H8A 109.2 . . ?
N7 C8 H8B 109.2 . . ?
N7 C8 C9 112.24(11) . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
N10 C9 C8 112.25(11) . . ?
N10 C9 H9A 109.2 . . ?
N10 C9 H9B 109.2 . . ?
C8 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
N10 C11 H11A 109.2 . . ?
N10 C11 H11B 109.2 . . ?
N10 C11 C12 112.06(11) . . ?
H11A C11 H11B 107.9 . . ?
C12 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
N7 C12 C11 112.19(11) . . ?
N7 C12 H12A 109.2 . . ?
N7 C12 H12B 109.2 . . ?
C11 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C23 C22 C21 120.53(14) . . ?
C20 C21 C25 120.58(14) . . ?
C22 C21 C20 118.27(14) . . ?
C22 C21 C25 121.15(14) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 C24 120.58(13) . . ?
C22 C23 H23 119.7 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 C5 120.04(15) . . ?
C3 C4 H4 120.0 . . ?
N1 C6 C5 124.86(15) . . ?
N1 C6 H6 117.6 . . ?
C5 C6 H6 117.6 . . ?
N1 C2 H2 118.8 . . ?
N1 C2 C3 122.48(15) . . ?
C3 C2 H2 118.8 . . ?
C4 C3 C2 119.79(16) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C21 C25 H25A 109.5 . . ?
C21 C25 H25B 109.5 . . ?
C21 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

_olex2_date_sample_data_collection 2018-04-07
_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 1.603
_oxdiff_exptl_absorpt_empirical_full_min 0.671
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EtOAc:Hexanes'
_chemical_compound_source        Synthesis
####################################################################### 
# 
# 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_19JLR003_MRC129
_database_code_depnum_ccdc_archive 'CCDC 1997205'
loop_
_audit_author_name
_audit_author_address
'Michal Andrzejewski'
;Department of Chemistry and Biochemistry, University of Bern
Switzerland
;
_audit_update_record             
;
2020-04-15 deposited with the CCDC.	2020-06-25 downloaded from the CCDC.
;
_audit_creation_date             2019-04-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            40
_chemical_name_systematic        
5-((4-((1r,4r)-4-hydroxy-4-(2-(trifluoromethyl)phenyl)cyclohexyl)piperazin-1-yl)methyl)pyridin-2(1H)-one
_chemical_formula_moiety         'C23 H29 F3 N3 O2, C2 F3 O2, C4 H10 O'
_chemical_formula_sum            'C29 H39 F6 N3 O5'
_chemical_formula_weight         623.63
_chemical_melting_point          ?
_chemical_oxdiff_formula         C25H29F6N3O5
_chemical_oxdiff_usercomment     MRC129
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'
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                   15.6425(3)
_cell_length_b                   12.7231(2)
_cell_length_c                   16.3931(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.097(2)
_cell_angle_gamma                90
_cell_volume                     3134.66(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6001
_cell_measurement_temperature    172.98(10)
_cell_measurement_theta_max      68.8830
_cell_measurement_theta_min      3.4550
_shelx_estimated_absorpt_T_max   0.930
_shelx_estimated_absorpt_T_min   0.829
_exptl_absorpt_coefficient_mu    0.977
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45522
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.075
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            24071
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.606
_diffrn_reflns_theta_min         3.456
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      172.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -32.00  83.00   0.50    0.05    --    0.00  23.00 152.00  230
  2  ω    -37.00  26.00   0.50    0.16    --   56.14 -23.00 -12.00  126
  3  ω    -32.00 138.00   0.50    0.16    --   56.14  23.00 152.00  340
  4  ω     18.00 174.00   0.50    0.16    --  112.28  23.00 152.00  312
  5  ω    -94.00  26.00   0.50    0.05    --    0.00 -23.00 -12.00  240
  6  ω   -124.00 -76.00   0.50    0.16    --  -29.00 -91.00-150.00   96
  7  ω     32.00 117.00   0.50    0.16    --   56.14-125.00 120.00  170
  8  ω     92.00 138.00   0.50    0.16    --   56.14 125.00  60.00   92
  9  ω     32.00 117.00   0.50    0.16    --   56.14-125.00  60.00  170
 10  ω     92.00 138.00   0.50    0.16    --   56.14 125.00  30.00   92
 11  ω    -27.00  62.00   0.50    0.16    --   56.14 -57.00-180.00  178
 12  ω    -39.00  23.00   0.50    0.16    --   56.14 -19.00-120.00  124
 13  ω     28.00  71.00   0.50    0.16    --  112.28 -63.00  60.00   86
 14  ω    100.00 174.00   0.50    0.16    --  112.28 111.00 150.00  148
 15  ω    100.00 174.00   0.50    0.16    --  112.28 111.00  30.00  148
 16  ω     28.00  71.00   0.50    0.16    --  112.28 -63.00 120.00   86
 17  ω     19.00 102.00   0.50    0.16    --  112.28 -77.00 -90.00  166
 18  ω     28.00  71.00   0.50    0.16    --  112.28 -63.00 150.00   86
 19  ω     28.00  71.00   0.50    0.16    --  112.28 -63.00   0.00   86
 20  ω     73.00 174.00   0.50    0.16    --  112.28  63.00-180.00  202
 21  ω     28.00  71.00   0.50    0.16    --  112.28 -63.00 -60.00   86
 22  ω     28.00  71.00   0.50    0.16    --  112.28 -63.00 -30.00   86
 23  ω     28.00  71.00   0.50    0.16    --  112.28 -63.00  90.00   86
 24  ω     28.00  71.00   0.50    0.16    --  112.28 -63.00  30.00   86
 25  ω     19.00 102.00   0.50    0.16    --  112.28 -77.00-150.00  166
 26  ω     67.00 174.00   0.50    0.16    --  112.28  50.00 -60.00  214
 27  ω     28.00  71.00   0.50    0.16    --  112.28 -63.00-150.00   86
 28  ω   -100.00 -36.00   0.50    0.05    --    0.00 178.00   0.00  128
 29  ω    -47.00  83.00   0.50    0.05    --    0.00  77.00  30.00  260
 30  ω     10.00 134.00   0.50    0.16    --   56.14  77.00 -90.00  248
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0620808000
_diffrn_orient_matrix_UB_12      -0.0124254000
_diffrn_orient_matrix_UB_13      -0.0906115000
_diffrn_orient_matrix_UB_21      -0.0760014000
_diffrn_orient_matrix_UB_22      -0.0346934000
_diffrn_orient_matrix_UB_23      0.0368830000
_diffrn_orient_matrix_UB_31      -0.0296009000
_diffrn_orient_matrix_UB_32      0.1153214000
_diffrn_orient_matrix_UB_33      0.0012841000
_diffrn_oxdiff_digest_frames     
;
014a6373326fb853a8b999829a08516ffe02404a98a
;
_diffrn_oxdiff_digest_hkl        
;
017bf7c1840531a5c78d01b8d4ef5c6b3d5aed
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4771
_reflns_number_total             6049
_reflns_odcompleteness_completeness 99.95
_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 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.147
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.101
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     402
_refine_ls_number_reflns         6049
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0897
_refine_ls_R_factor_gt           0.0759
_refine_ls_restrained_S_all      1.051
_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)+(0.1712P)²+1.1095P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2374
_refine_ls_wR_factor_ref         0.2551
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O21-H21
 0.98 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C15(H15)
3.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C20(H20A,H20B), C10(H10A,H10B), C19(H19A,H19B), C11(H11A,
 H11B), C13(H13A,H13B), C14(H14A,H14B), C16(H16A,H16B), C8(H8A,H8B), C34(H34A,
 H34B), C36(H36A,H36B)
3.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C23(H23), C6(H6), C24(H24), C7(H7), C26(H26), C25(H25)
3.d Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C37(H37A,H37B,H37C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F3 F 0.43629(12) 1.41777(13) 0.94453(11) 0.0566(5) Uani 1 1 d . . . . .
O21 O 0.37837(12) 1.31084(14) 0.79919(11) 0.0440(5) Uani 1 1 d D . . . .
O32 O 0.38211(12) 0.92802(15) 0.93770(11) 0.0468(5) Uani 1 1 d . . . . .
F2 F 0.32510(15) 1.49156(15) 0.85345(12) 0.0703(6) Uani 1 1 d . . . . .
F1 F 0.34512(18) 1.51412(16) 0.98657(14) 0.0823(7) Uani 1 1 d . . . . .
O31 O 0.27072(14) 0.87718(18) 0.82742(12) 0.0533(5) Uani 1 1 d . . . . .
O1 O 0.51278(17) 0.37339(16) 0.54769(13) 0.0581(6) Uani 1 1 d . . . . .
N12 N 0.46747(14) 0.96014(17) 0.80981(13) 0.0386(5) Uani 1 1 d . . . . .
N9 N 0.53208(14) 0.74491(17) 0.80678(13) 0.0413(5) Uani 1 1 d . . . . .
N3 N 0.52701(16) 0.53542(19) 0.60902(15) 0.0443(5) Uani 1 1 d . . . . .
F4 F 0.26148(19) 0.9058(3) 1.02881(15) 0.1006(9) Uani 1 1 d . . . . .
F5 F 0.18027(18) 0.8097(4) 0.92977(16) 0.1320(15) Uani 1 1 d . . . . .
C17 C 0.44714(16) 1.17863(19) 0.89700(15) 0.0371(5) Uani 1 1 d . . . . .
H17A H 0.4749 1.2316 0.9384 0.045 Uiso 1 1 calc R . . . .
H17B H 0.4365 1.1169 0.9275 0.045 Uiso 1 1 calc R . . . .
C18 C 0.35795(16) 1.2207(2) 0.84099(15) 0.0384(5) Uani 1 1 d . . . . .
C5 C 0.53332(18) 0.5638(2) 0.75295(16) 0.0419(6) Uani 1 1 d . . . . .
C20 C 0.38004(18) 1.1094(2) 0.72053(16) 0.0439(6) Uani 1 1 d . . . . .
H20A H 0.3886 1.1712 0.6891 0.053 Uiso 1 1 calc R . . . .
H20B H 0.3529 1.0555 0.6796 0.053 Uiso 1 1 calc R . . . .
C10 C 0.56451(18) 0.8110(2) 0.88189(16) 0.0448(6) Uani 1 1 d . . . . .
H10A H 0.6255 0.7920 0.9107 0.054 Uiso 1 1 calc R . . . .
H10B H 0.5287 0.7989 0.9207 0.054 Uiso 1 1 calc R . . . .
C19 C 0.31692(17) 1.1364(2) 0.77320(16) 0.0415(6) Uani 1 1 d . . . . .
H19A H 0.3040 1.0735 0.8010 0.050 Uiso 1 1 calc R . . . .
H19B H 0.2614 1.1626 0.7362 0.050 Uiso 1 1 calc R . . . .
C11 C 0.56038(17) 0.9251(2) 0.85810(17) 0.0438(6) Uani 1 1 d . . . . .
H11A H 0.6005 0.9378 0.8234 0.053 Uiso 1 1 calc R . . . .
H11B H 0.5807 0.9669 0.9093 0.053 Uiso 1 1 calc R . . . .
C29 C 0.30845(18) 0.8876(2) 0.90357(17) 0.0426(6) Uani 1 1 d . . . . .
C22 C 0.29692(17) 1.2478(2) 0.89720(16) 0.0442(6) Uani 1 1 d . . . . .
C13 C 0.42800(17) 0.8832(2) 0.73971(16) 0.0421(6) Uani 1 1 d . . . . .
H13A H 0.4570 0.8916 0.6949 0.050 Uiso 1 1 calc R . . . .
H13B H 0.3653 0.8988 0.7160 0.050 Uiso 1 1 calc R . . . .
C14 C 0.43788(18) 0.7706(2) 0.76989(17) 0.0443(6) Uani 1 1 d . . . . .
H14A H 0.4058 0.7603 0.8121 0.053 Uiso 1 1 calc R . . . .
H14B H 0.4125 0.7240 0.7225 0.053 Uiso 1 1 calc R . . . .
F6 F 0.3056(3) 0.7599(3) 1.0085(2) 0.1265(12) Uani 1 1 d . . . . .
C4 C 0.53358(18) 0.6009(2) 0.67586(16) 0.0427(6) Uani 1 1 d . . . . .
H4 H 0.5384 0.6729 0.6684 0.051 Uiso 1 1 calc R . . . .
C2 C 0.5198(2) 0.4290(2) 0.61298(18) 0.0474(6) Uani 1 1 d . . . . .
C15 C 0.47079(17) 1.0704(2) 0.77375(15) 0.0403(6) Uani 1 1 d . . . . .
H15 H 0.5102 1.0675 0.7366 0.048 Uiso 1 1 calc R . . . .
C16 C 0.50999(16) 1.1501(2) 0.84383(16) 0.0401(6) Uani 1 1 d . . . . .
H16A H 0.5253 1.2135 0.8182 0.048 Uiso 1 1 calc R . . . .
H16B H 0.5645 1.1215 0.8810 0.048 Uiso 1 1 calc R . . . .
C27 C 0.29184(19) 1.3473(2) 0.93383(18) 0.0505(7) Uani 1 1 d . . . . .
C8 C 0.5439(2) 0.6337(2) 0.82904(16) 0.0463(6) Uani 1 1 d . . . . .
H8A H 0.5007 0.6134 0.8586 0.056 Uiso 1 1 calc R . . . .
H8B H 0.6028 0.6234 0.8675 0.056 Uiso 1 1 calc R . . . .
C28 C 0.3494(2) 1.4409(2) 0.9284(2) 0.0591(8) Uani 1 1 d . . . . .
C23 C 0.24393(19) 1.1687(3) 0.91561(19) 0.0543(7) Uani 1 1 d . . . . .
H23 H 0.2477 1.1020 0.8938 0.065 Uiso 1 1 calc R . . . .
C6 C 0.5252(2) 0.4540(2) 0.76019(18) 0.0545(7) Uani 1 1 d . . . . .
H6 H 0.5237 0.4254 0.8120 0.065 Uiso 1 1 calc R . . . .
C24 C 0.1860(2) 1.1838(4) 0.9646(2) 0.0673(10) Uani 1 1 d . . . . .
H24 H 0.1528 1.1279 0.9762 0.081 Uiso 1 1 calc R . . . .
C7 C 0.5196(3) 0.3896(2) 0.6938(2) 0.0598(8) Uani 1 1 d . . . . .
H7 H 0.5155 0.3175 0.7012 0.072 Uiso 1 1 calc R . . . .
C30 C 0.2597(2) 0.8426(3) 0.9651(2) 0.0656(9) Uani 1 1 d . . . . .
C26 C 0.2308(2) 1.3631(3) 0.9809(2) 0.0689(10) Uani 1 1 d . . . . .
H26 H 0.2255 1.4295 1.0027 0.083 Uiso 1 1 calc R . . . .
C25 C 0.1780(2) 1.2812(4) 0.9956(2) 0.0760(12) Uani 1 1 d . . . . .
H25 H 0.1373 1.2931 1.0266 0.091 Uiso 1 1 calc R . . . .
H12 H 0.426(2) 0.964(3) 0.847(2) 0.057(9) Uiso 1 1 d . . . . .
H3 H 0.524(2) 0.562(2) 0.564(2) 0.043(8) Uiso 1 1 d . . . . .
H21 H 0.318(2) 1.326(5) 0.762(3) 0.13(2) Uiso 1 1 d D . . . .
O35 O 0.6477(3) 0.9950(3) 0.6485(4) 0.1293(16) Uani 1 1 d . . . . .
C34 C 0.7255(4) 1.0240(7) 0.7134(5) 0.128(2) Uani 1 1 d . . . . .
H34A H 0.7772 1.0181 0.6919 0.154 Uiso 1 1 calc R . . . .
H34B H 0.7336 0.9765 0.7612 0.154 Uiso 1 1 calc R . . . .
C33 C 0.7180(5) 1.1333(7) 0.7419(4) 0.134(3) Uani 1 1 d . . . . .
H33A H 0.7152 1.1809 0.6958 0.201 Uiso 1 1 calc GR . . . .
H33B H 0.7690 1.1498 0.7884 0.201 Uiso 1 1 calc GR . . . .
H33C H 0.6650 1.1401 0.7601 0.201 Uiso 1 1 calc GR . . . .
C36 C 0.6482(6) 0.8935(6) 0.6159(7) 0.151(3) Uani 1 1 d . . . . .
H36A H 0.6508 0.8430 0.6608 0.181 Uiso 1 1 calc R . . . .
H36B H 0.7014 0.8846 0.5972 0.181 Uiso 1 1 calc R . . . .
C37 C 0.5734(8) 0.8719(8) 0.5478(8) 0.195(5) Uani 1 1 d . . . . .
H37A H 0.5770 0.9113 0.4989 0.293 Uiso 1 1 calc GR . . . .
H37B H 0.5205 0.8915 0.5629 0.293 Uiso 1 1 calc GR . . . .
H37C H 0.5715 0.7982 0.5350 0.293 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F3 C28 1.343(4) . ?
O21 C18 1.417(3) . ?
O21 H21 0.99(2) . ?
O32 C29 1.244(3) . ?
F2 C28 1.345(4) . ?
F1 C28 1.348(4) . ?
O31 C29 1.231(3) . ?
O1 C2 1.262(3) . ?
N12 C11 1.517(3) . ?
N12 C13 1.506(3) . ?
N12 C15 1.528(3) . ?
N12 H12 1.00(4) . ?
N9 C10 1.461(3) . ?
N9 C14 1.466(3) . ?
N9 C8 1.460(4) . ?
N3 C4 1.358(3) . ?
N3 C2 1.362(4) . ?
N3 H3 0.80(3) . ?
F4 C30 1.312(4) . ?
F5 C30 1.287(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.538(3) . ?
C17 C16 1.528(4) . ?
C18 C19 1.549(3) . ?
C18 C22 1.539(4) . ?
C5 C4 1.350(4) . ?
C5 C8 1.503(4) . ?
C5 C6 1.411(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C19 1.520(4) . ?
C20 C15 1.528(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.500(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C29 C30 1.533(4) . ?
C22 C27 1.412(4) . ?
C22 C23 1.389(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.509(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
F6 C30 1.359(5) . ?
C4 H4 0.9300 . ?
C2 C7 1.418(4) . ?
C15 H15 0.9800 . ?
C15 C16 1.528(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C27 C28 1.511(5) . ?
C27 C26 1.398(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C23 H23 0.9300 . ?
C23 C24 1.381(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.345(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.359(6) . ?
C7 H7 0.9300 . ?
C26 H26 0.9300 . ?
C26 C25 1.393(6) . ?
C25 H25 0.9300 . ?
O35 C34 1.426(8) . ?
O35 C36 1.399(9) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C34 C33 1.483(10) . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C36 C37 1.402(13) . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?

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
C18 O21 H21 99(3) . . ?
C11 N12 C15 109.97(19) . . ?
C11 N12 H12 113(2) . . ?
C13 N12 C11 109.7(2) . . ?
C13 N12 C15 110.63(18) . . ?
C13 N12 H12 107(2) . . ?
C15 N12 H12 106(2) . . ?
C10 N9 C14 107.1(2) . . ?
C8 N9 C10 110.9(2) . . ?
C8 N9 C14 111.2(2) . . ?
C4 N3 C2 124.1(2) . . ?
C4 N3 H3 117(2) . . ?
C2 N3 H3 119(2) . . ?
H17A C17 H17B 108.0 . . ?
C18 C17 H17A 109.4 . . ?
C18 C17 H17B 109.4 . . ?
C16 C17 H17A 109.4 . . ?
C16 C17 H17B 109.4 . . ?
C16 C17 C18 111.3(2) . . ?
O21 C18 C17 106.34(19) . . ?
O21 C18 C19 108.5(2) . . ?
O21 C18 C22 111.6(2) . . ?
C17 C18 C19 108.3(2) . . ?
C17 C18 C22 109.36(19) . . ?
C22 C18 C19 112.5(2) . . ?
C4 C5 C8 122.8(2) . . ?
C4 C5 C6 116.6(3) . . ?
C6 C5 C8 120.5(2) . . ?
H20A C20 H20B 107.7 . . ?
C19 C20 H20A 108.9 . . ?
C19 C20 H20B 108.9 . . ?
C19 C20 C15 113.3(2) . . ?
C15 C20 H20A 108.9 . . ?
C15 C20 H20B 108.9 . . ?
N9 C10 H10A 109.4 . . ?
N9 C10 H10B 109.4 . . ?
N9 C10 C11 111.0(2) . . ?
H10A C10 H10B 108.0 . . ?
C11 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
C18 C19 H19A 109.4 . . ?
C18 C19 H19B 109.4 . . ?
C20 C19 C18 111.0(2) . . ?
C20 C19 H19A 109.4 . . ?
C20 C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?
N12 C11 H11A 109.0 . . ?
N12 C11 H11B 109.0 . . ?
C10 C11 N12 112.7(2) . . ?
C10 C11 H11A 109.0 . . ?
C10 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
O32 C29 C30 115.2(2) . . ?
O31 C29 O32 128.6(3) . . ?
O31 C29 C30 116.1(2) . . ?
C27 C22 C18 125.0(3) . . ?
C23 C22 C18 118.3(3) . . ?
C23 C22 C27 116.7(3) . . ?
N12 C13 H13A 109.1 . . ?
N12 C13 H13B 109.1 . . ?
N12 C13 C14 112.6(2) . . ?
H13A C13 H13B 107.8 . . ?
C14 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
N9 C14 C13 110.3(2) . . ?
N9 C14 H14A 109.6 . . ?
N9 C14 H14B 109.6 . . ?
C13 C14 H14A 109.6 . . ?
C13 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
N3 C4 H4 119.3 . . ?
C5 C4 N3 121.5(3) . . ?
C5 C4 H4 119.3 . . ?
O1 C2 N3 120.4(3) . . ?
O1 C2 C7 124.9(3) . . ?
N3 C2 C7 114.7(3) . . ?
N12 C15 C20 113.1(2) . . ?
N12 C15 H15 107.5 . . ?
C20 C15 H15 107.5 . . ?
C16 C15 N12 111.58(19) . . ?
C16 C15 C20 109.2(2) . . ?
C16 C15 H15 107.5 . . ?
C17 C16 H16A 108.9 . . ?
C17 C16 H16B 108.9 . . ?
C15 C16 C17 113.5(2) . . ?
C15 C16 H16A 108.9 . . ?
C15 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C22 C27 C28 125.2(3) . . ?
C26 C27 C22 119.4(3) . . ?
C26 C27 C28 115.3(3) . . ?
N9 C8 C5 112.9(2) . . ?
N9 C8 H8A 109.0 . . ?
N9 C8 H8B 109.0 . . ?
C5 C8 H8A 109.0 . . ?
C5 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
F3 C28 F2 107.4(3) . . ?
F3 C28 F1 105.0(3) . . ?
F3 C28 C27 113.7(2) . . ?
F2 C28 F1 105.0(2) . . ?
F2 C28 C27 114.2(3) . . ?
F1 C28 C27 110.8(3) . . ?
C22 C23 H23 118.2 . . ?
C24 C23 C22 123.6(3) . . ?
C24 C23 H23 118.2 . . ?
C5 C6 H6 119.3 . . ?
C7 C6 C5 121.5(3) . . ?
C7 C6 H6 119.3 . . ?
C23 C24 H24 120.4 . . ?
C25 C24 C23 119.2(4) . . ?
C25 C24 H24 120.4 . . ?
C2 C7 H7 119.2 . . ?
C6 C7 C2 121.6(3) . . ?
C6 C7 H7 119.2 . . ?
F4 C30 C29 113.0(3) . . ?
F4 C30 F6 99.5(3) . . ?
F5 C30 F4 111.2(4) . . ?
F5 C30 C29 114.8(3) . . ?
F5 C30 F6 106.7(4) . . ?
F6 C30 C29 110.3(3) . . ?
C27 C26 H26 119.4 . . ?
C25 C26 C27 121.1(4) . . ?
C25 C26 H26 119.4 . . ?
C24 C25 C26 119.8(3) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C36 O35 C34 115.5(6) . . ?
O35 C34 H34A 109.5 . . ?
O35 C34 H34B 109.5 . . ?
O35 C34 C33 110.6(6) . . ?
H34A C34 H34B 108.1 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
C34 C33 H33A 109.5 . . ?
C34 C33 H33B 109.5 . . ?
C34 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
O35 C36 H36A 109.0 . . ?
O35 C36 H36B 109.0 . . ?
O35 C36 C37 113.1(8) . . ?
H36A C36 H36B 107.8 . . ?
C37 C36 H36A 109.0 . . ?
C37 C36 H36B 109.0 . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?

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
O21 C18 C19 C20 57.6(3) . . . . ?
O21 C18 C22 C27 -26.2(3) . . . . ?
O21 C18 C22 C23 155.5(2) . . . . ?
O32 C29 C30 F4 44.9(4) . . . . ?
O32 C29 C30 F5 173.9(4) . . . . ?
O32 C29 C30 F6 -65.5(4) . . . . ?
O31 C29 C30 F4 -136.5(3) . . . . ?
O31 C29 C30 F5 -7.5(5) . . . . ?
O31 C29 C30 F6 113.2(3) . . . . ?
O1 C2 C7 C6 -178.4(3) . . . . ?
N12 C13 C14 N9 -58.3(3) . . . . ?
N12 C15 C16 C17 -73.3(3) . . . . ?
N9 C10 C11 N12 57.1(3) . . . . ?
N3 C2 C7 C6 0.7(5) . . . . ?
C17 C18 C19 C20 -57.4(3) . . . . ?
C17 C18 C22 C27 91.2(3) . . . . ?
C17 C18 C22 C23 -87.1(3) . . . . ?
C18 C17 C16 C15 -56.5(3) . . . . ?
C18 C22 C27 C28 -4.0(4) . . . . ?
C18 C22 C27 C26 177.3(2) . . . . ?
C18 C22 C23 C24 -179.4(3) . . . . ?
C5 C6 C7 C2 -1.3(6) . . . . ?
C20 C15 C16 C17 52.6(3) . . . . ?
C10 N9 C14 C13 64.1(3) . . . . ?
C10 N9 C8 C5 -165.6(2) . . . . ?
C19 C18 C22 C27 -148.4(2) . . . . ?
C19 C18 C22 C23 33.3(3) . . . . ?
C19 C20 C15 N12 71.8(3) . . . . ?
C19 C20 C15 C16 -53.2(3) . . . . ?
C11 N12 C13 C14 48.5(3) . . . . ?
C11 N12 C15 C20 177.3(2) . . . . ?
C11 N12 C15 C16 -59.0(3) . . . . ?
C22 C18 C19 C20 -178.4(2) . . . . ?
C22 C27 C28 F3 -46.2(4) . . . . ?
C22 C27 C28 F2 77.6(4) . . . . ?
C22 C27 C28 F1 -164.1(2) . . . . ?
C22 C27 C26 C25 3.1(4) . . . . ?
C22 C23 C24 C25 1.4(5) . . . . ?
C13 N12 C11 C10 -47.8(3) . . . . ?
C13 N12 C15 C20 55.9(3) . . . . ?
C13 N12 C15 C16 179.6(2) . . . . ?
C14 N9 C10 C11 -63.8(3) . . . . ?
C14 N9 C8 C5 75.3(3) . . . . ?
C4 N3 C2 O1 179.1(3) . . . . ?
C4 N3 C2 C7 -0.1(4) . . . . ?
C4 C5 C8 N9 14.4(4) . . . . ?
C4 C5 C6 C7 1.1(5) . . . . ?
C2 N3 C4 C5 -0.1(4) . . . . ?
C15 N12 C11 C10 -169.8(2) . . . . ?
C15 N12 C13 C14 170.0(2) . . . . ?
C15 C20 C19 C18 57.4(3) . . . . ?
C16 C17 C18 O21 -59.6(3) . . . . ?
C16 C17 C18 C19 56.8(3) . . . . ?
C16 C17 C18 C22 179.8(2) . . . . ?
C27 C22 C23 C24 2.2(4) . . . . ?
C27 C26 C25 C24 0.6(5) . . . . ?
C8 N9 C10 C11 174.7(2) . . . . ?
C8 N9 C14 C13 -174.6(2) . . . . ?
C8 C5 C4 N3 177.7(3) . . . . ?
C8 C5 C6 C7 -177.0(3) . . . . ?
C28 C27 C26 C25 -175.7(3) . . . . ?
C23 C22 C27 C28 174.3(3) . . . . ?
C23 C22 C27 C26 -4.3(4) . . . . ?
C23 C24 C25 C26 -2.8(5) . . . . ?
C6 C5 C4 N3 -0.4(4) . . . . ?
C6 C5 C8 N9 -167.6(3) . . . . ?
C26 C27 C28 F3 132.5(3) . . . . ?
C26 C27 C28 F2 -103.7(3) . . . . ?
C26 C27 C28 F1 14.6(4) . . . . ?
C34 O35 C36 C37 -175.2(7) . . . . ?
C36 O35 C34 C33 179.1(6) . . . . ?

_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 1.416
_oxdiff_exptl_absorpt_empirical_full_min 0.431
_exptl_crystal_recrystallization_method 'Vapour deposition'
_chemical_compound_source        Synthesis
####################################################################### 
# 
# 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_19jlr007_mrc65
_database_code_depnum_ccdc_archive 'CCDC 1997203'
loop_
_audit_author_name
_audit_author_address
'Jurg Hauser'
;Department of Chemistry and Biochemistry, University of Bern
Switzerland
;
_audit_update_record             
;
2020-04-15 deposited with the CCDC.	2020-06-25 downloaded from the CCDC.
;
_audit_creation_date             2019-06-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            9
_chemical_name_systematic        
2-methoxy-4-((4-((1s,4s)-4-phenylcyclohexyl)piperazin-1-yl)methyl)phenol
_chemical_formula_moiety         'C24 H34 N2 O2, 2(C2 F3 O2)'
_chemical_formula_sum            'C28 H34 F6 N2 O6'
_chemical_formula_weight         608.57
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
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                   12.18020(10)
_cell_length_b                   16.45030(10)
_cell_length_c                   14.08290(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.2560(10)
_cell_angle_gamma                90
_cell_volume                     2817.21(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    17811
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      75.9770
_cell_measurement_theta_min      3.1370
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.093
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.327
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1272
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.0961
-1 0 0 0.0961
0 -1 1 0.1015
0 1 -1 0.1015
0 -1 -1 0.1255
0 1 1 0.1255

_exptl_crystal_size_max          0.293
_exptl_crystal_size_mid          0.203
_exptl_crystal_size_min          0.192
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0142
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            27224
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.140
_diffrn_reflns_theta_min         3.635
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -39.00  55.00   0.50    0.25    --  -18.75  71.00 -90.00  188
  2  ω     28.00 120.00   0.50    0.25    --   47.95  71.00 -90.00  184
  3  ω    -23.00  69.00   0.50    0.25    --   47.95 -71.00 138.00  184
  4  ω     35.00  86.00   0.50    1.00    --  107.11 -71.00 138.00  102
  5  ω     87.00 174.00   0.50    1.00    --  107.11  71.00 -90.00  174
  6  ω    -90.00   2.00   0.50    0.25    --  -18.75 -71.00 138.00  184
  7  ω    -66.00  -9.00   0.50    0.25    --  -18.75 125.00-180.00  114
  8  ω    -26.00  23.00   0.50    0.25    --   47.95 -19.00 120.00   98
  9  ω    -26.00  23.00   0.50    0.25    --   47.95 -19.00 150.00   98
 10  ω    -26.00  23.00   0.50    0.25    --   47.95 -19.00 -30.00   98
 11  ω     35.00 102.00   0.50    1.00    --  107.11 -77.00-180.00  134
 12  ω     35.00  68.00   0.50    1.00    --  107.11 -61.00  60.00   66
 13  ω     35.00  68.00   0.50    1.00    --  107.11 -61.00-150.00   66
 14  ω     35.00 102.00   0.50    1.00    --  107.11 -77.00 -30.00  134
 15  ω     35.00  68.00   0.50    1.00    --  107.11 -61.00-180.00   66
 16  ω     95.00 174.00   0.50    1.00    --  107.11  45.00-150.00  158
 17  ω     95.00 174.00   0.50    1.00    --  107.11  45.00 -30.00  158
 18  ω     35.00  68.00   0.50    1.00    --  107.11 -61.00 -90.00   66
 19  ω     35.00 109.00   0.50    1.00    --  107.11 -94.00  30.00  148
 20  ω     35.00  68.00   0.50    1.00    --  107.11 -61.00-120.00   66
 21  ω     35.00  68.00   0.50    1.00    --  107.11 -61.00  30.00   66
 22  ω     95.00 174.00   0.50    1.00    --  107.11  45.00 -90.00  158
 23  ω     95.00 174.00   0.50    1.00    --  107.11  45.00-180.00  158
 24  ω     33.00 120.00   0.50    0.25    --   47.95  57.00  90.00  174
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0115388000
_diffrn_orient_matrix_UB_12      -0.0679679000
_diffrn_orient_matrix_UB_13      0.0740485000
_diffrn_orient_matrix_UB_21      -0.1052620000
_diffrn_orient_matrix_UB_22      -0.0301314000
_diffrn_orient_matrix_UB_23      -0.0547988000
_diffrn_orient_matrix_UB_31      0.0695402000
_diffrn_orient_matrix_UB_32      -0.0569737000
_diffrn_orient_matrix_UB_33      -0.0592881000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5395
_reflns_number_total             5836
_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 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.517
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     447
_refine_ls_number_reflns         5836
_refine_ls_number_restraints     258
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.023
_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)+(0.0615P)²+0.9881P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1173
_refine_ls_wR_factor_ref         0.1192
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C19A \\sim C19 \\sim C20 \\sim C20A \\sim C21A \\sim C21 \\sim C22 \\sim C22A
\\sim C23A \\sim C23 \\sim C24 \\sim C24A: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08
3. Rigid body (RIGU) restrains
 C19A, C19, C20, C20A, C21A, C21, C22, C22A, C23A, C23, C24, C24A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(H16A)=Sof(C19A)=Sof(C20A)=Sof(H20A)=Sof(C21A)=Sof(H21A)=Sof(C22A)=
 Sof(H22A)=Sof(C23A)=Sof(H23A)=Sof(C24A)=Sof(H24A)=1-FVAR(1)
 Sof(H16)=Sof(C19)=Sof(C20)=Sof(H20)=Sof(C21)=Sof(H21)=Sof(C22)=Sof(H22)=
 Sof(C23)=Sof(H23)=Sof(C24)=Sof(H24)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C13(H13), C16(H16), C16(H16A)
5.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B),
 C14(H14A,H14B), C15(H15A,H15B), C17(H17A,H17B), C18(H18A,H18B)
5.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C20(H20), C20A(H20A), C21A(H21A), C21(H21), C22(H22),
 C22A(H22A), C23A(H23A), C23(H23), C24(H24), C24A(H24A)
5.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.70792(9) 0.77769(7) 0.67601(8) 0.0429(2) Uani 1 1 d . . . . .
H1 H 0.741(2) 0.7360(15) 0.7066(17) 0.073(7) Uiso 1 1 d . . . . .
N1 N 0.17411(9) 0.77432(7) 0.63607(8) 0.0329(2) Uani 1 1 d . . . . .
H1A H 0.1894(16) 0.8136(12) 0.5865(14) 0.054(5) Uiso 1 1 d . . . . .
C1 C 0.59731(12) 0.77685(9) 0.68538(10) 0.0377(3) Uani 1 1 d . . . . .
O2 O 0.61951(9) 0.66383(8) 0.78372(9) 0.0514(3) Uani 1 1 d . . . . .
N2 N -0.01122(9) 0.70299(7) 0.52208(8) 0.0304(2) Uani 1 1 d . . . . .
H2 H -0.0358(15) 0.6636(12) 0.5619(13) 0.045(5) Uiso 1 1 d . . . . .
C2 C 0.54765(12) 0.71890(9) 0.74201(10) 0.0393(3) Uani 1 1 d . . . . .
C3 C 0.43476(12) 0.72086(9) 0.75101(10) 0.0402(3) Uani 1 1 d . . . . .
H3 H 0.401925 0.682196 0.788341 0.048 Uiso 1 1 calc R . . . .
C4 C 0.37025(12) 0.78023(9) 0.70461(10) 0.0382(3) Uani 1 1 d . . . . .
C5 C 0.41974(13) 0.83707(10) 0.64807(11) 0.0430(3) Uani 1 1 d . . . . .
H5 H 0.377310 0.876849 0.616661 0.052 Uiso 1 1 calc R . . . .
C6 C 0.53308(13) 0.83463(10) 0.63825(11) 0.0430(3) Uani 1 1 d . . . . .
H6 H 0.565564 0.872405 0.599502 0.052 Uiso 1 1 calc R . . . .
C7 C 0.57766(18) 0.60627(14) 0.84753(16) 0.0704(6) Uani 1 1 d . . . . .
H7A H 0.527255 0.570508 0.813317 0.106 Uiso 1 1 calc GR . . . .
H7B H 0.540124 0.634206 0.895997 0.106 Uiso 1 1 calc GR . . . .
H7C H 0.637320 0.575174 0.876423 0.106 Uiso 1 1 calc GR . . . .
C8 C 0.24971(12) 0.78613(10) 0.72293(10) 0.0406(3) Uani 1 1 d . . . . .
H8A H 0.232638 0.745557 0.769843 0.049 Uiso 1 1 calc R . . . .
H8B H 0.235588 0.839135 0.749849 0.049 Uiso 1 1 calc R . . . .
C9 C 0.18085(11) 0.69112(8) 0.59596(10) 0.0356(3) Uani 1 1 d . . . . .
H9A H 0.158739 0.651789 0.642513 0.043 Uiso 1 1 calc R . . . .
H9B H 0.256238 0.679468 0.581723 0.043 Uiso 1 1 calc R . . . .
C10 C 0.10728(11) 0.68342(8) 0.50635(10) 0.0339(3) Uani 1 1 d . . . . .
H10A H 0.133505 0.719832 0.458429 0.041 Uiso 1 1 calc R . . . .
H10B H 0.111933 0.628342 0.482306 0.041 Uiso 1 1 calc R . . . .
C11 C -0.01854(11) 0.78363(8) 0.57159(10) 0.0348(3) Uani 1 1 d . . . . .
H11A H -0.093480 0.791969 0.589406 0.042 Uiso 1 1 calc R . . . .
H11B H -0.001045 0.826568 0.527725 0.042 Uiso 1 1 calc R . . . .
C12 C 0.05796(11) 0.78962(8) 0.65923(10) 0.0353(3) Uani 1 1 d . . . . .
H12A H 0.052211 0.843368 0.686832 0.042 Uiso 1 1 calc R . . . .
H12B H 0.036374 0.750203 0.705893 0.042 Uiso 1 1 calc R . . . .
C13 C -0.07903(11) 0.70503(9) 0.42719(10) 0.0354(3) Uani 1 1 d . . . . .
H13 H -0.048437 0.747522 0.387692 0.043 Uiso 1 1 calc R . . . .
C14 C -0.19934(11) 0.72605(9) 0.44069(10) 0.0366(3) Uani 1 1 d . . . . .
H14A H -0.202594 0.774732 0.479297 0.044 Uiso 1 1 calc R . . . .
H14B H -0.235739 0.737738 0.379151 0.044 Uiso 1 1 calc R . . . .
C15 C -0.26070(11) 0.65773(8) 0.48808(10) 0.0337(3) Uani 1 1 d . . . . .
H15A H -0.337039 0.673277 0.492634 0.040 Uiso 1 1 calc R . . . .
H15B H -0.228967 0.649517 0.552096 0.040 Uiso 1 1 calc R . . . .
C16 C -0.25514(12) 0.57807(9) 0.43239(11) 0.0379(3) Uani 1 1 d . . . . .
H16 H -0.286198 0.590490 0.368313 0.045 Uiso 0.323(16) 1 calc R . P A 1
H16A H -0.291511 0.586272 0.369250 0.045 Uiso 0.677(16) 1 calc R . P A 2
C17 C -0.13437(12) 0.55555(9) 0.41997(11) 0.0389(3) Uani 1 1 d . . . . .
H17A H -0.098609 0.543427 0.481640 0.047 Uiso 1 1 calc R . . . .
H17B H -0.131207 0.507141 0.380886 0.047 Uiso 1 1 calc R . . . .
C18 C -0.07325(12) 0.62457(10) 0.37352(10) 0.0410(3) Uani 1 1 d . . . . .
H18A H -0.104159 0.632195 0.309130 0.049 Uiso 1 1 calc R . . . .
H18B H 0.003265 0.609241 0.369686 0.049 Uiso 1 1 calc R . . . .
C19A C -0.3180(9) 0.5088(7) 0.4846(6) 0.0340(13) Uani 0.677(16) 1 d . U P A 2
C19 C -0.312(2) 0.5110(16) 0.4616(13) 0.038(3) Uani 0.323(16) 1 d . U P A 1
C20 C -0.2904(7) 0.4813(7) 0.5516(11) 0.043(2) Uani 0.323(16) 1 d . U P A 1
H20 H -0.233675 0.504723 0.589231 0.051 Uiso 0.323(16) 1 calc R . P A 1
C20A C -0.3101(5) 0.4997(4) 0.5830(4) 0.0466(11) Uani 0.677(16) 1 d . U P A 2
H20A H -0.266805 0.535442 0.619995 0.056 Uiso 0.677(16) 1 calc R . P A 2
C21A C -0.3661(4) 0.4381(4) 0.6263(4) 0.0516(11) Uani 0.677(16) 1 d . U P A 2
H21A H -0.361391 0.433325 0.692235 0.062 Uiso 0.677(16) 1 calc R . P A 2
C21 C -0.3499(8) 0.4169(8) 0.5898(13) 0.057(3) Uani 0.323(16) 1 d . U P A 1
H21 H -0.335032 0.399874 0.652153 0.068 Uiso 0.323(16) 1 calc R . P A 1
C22 C -0.4315(9) 0.3794(7) 0.5322(14) 0.051(3) Uani 0.323(16) 1 d . U P A 1
H22 H -0.470589 0.335922 0.555730 0.061 Uiso 0.323(16) 1 calc R . P A 1
C22A C -0.4289(5) 0.3835(4) 0.5720(5) 0.0439(11) Uani 0.677(16) 1 d . U P A 2
H22A H -0.465400 0.341384 0.601014 0.053 Uiso 0.677(16) 1 calc R . P A 2
C23A C -0.4370(5) 0.3920(3) 0.4747(5) 0.0425(13) Uani 0.677(16) 1 d . U P A 2
H23A H -0.479109 0.355457 0.437729 0.051 Uiso 0.677(16) 1 calc R . P A 2
C23 C -0.4544(10) 0.4057(8) 0.4423(12) 0.044(2) Uani 0.323(16) 1 d . U P A 1
H23 H -0.509588 0.380637 0.404409 0.053 Uiso 0.323(16) 1 calc R . P A 1
C24 C -0.3958(13) 0.4698(10) 0.4065(11) 0.041(2) Uani 0.323(16) 1 d . U P A 1
H24 H -0.411927 0.486480 0.344199 0.050 Uiso 0.323(16) 1 calc R . P A 1
C24A C -0.3821(6) 0.4553(4) 0.4312(5) 0.0398(11) Uani 0.677(16) 1 d . U P A 2
H24A H -0.389136 0.461174 0.365418 0.048 Uiso 0.677(16) 1 calc R . P A 2
F1 F 0.99068(11) 0.49565(7) 0.81373(9) 0.0695(3) Uani 1 1 d . . . . .
F2 F 0.89645(12) 0.57802(7) 0.89233(7) 0.0709(4) Uani 1 1 d . . . . .
F3 F 0.81687(11) 0.49863(7) 0.79014(8) 0.0716(4) Uani 1 1 d . . . . .
O3 O 0.87230(8) 0.67735(6) 0.74367(8) 0.0415(2) Uani 1 1 d . . . . .
O4 O 0.95578(9) 0.58568(6) 0.65522(7) 0.0387(2) Uani 1 1 d . . . . .
C25 C 0.91224(11) 0.61003(8) 0.72788(9) 0.0326(3) Uani 1 1 d . . . . .
C26 C 0.90453(14) 0.54599(9) 0.80747(10) 0.0420(3) Uani 1 1 d . . . . .
F4 F 0.24705(16) 0.97474(9) 0.29385(9) 0.1000(5) Uani 1 1 d . . . . .
F5 F 0.35372(10) 0.97823(9) 0.41833(13) 0.0943(5) Uani 1 1 d . . . . .
O5 O 0.20198(10) 0.89442(7) 0.51585(8) 0.0504(3) Uani 1 1 d . . . . .
F6 F 0.20138(11) 1.04083(6) 0.41470(10) 0.0714(3) Uani 1 1 d . . . . .
O6 O 0.15322(13) 0.84732(8) 0.37009(9) 0.0631(4) Uani 1 1 d . . . . .
C27 C 0.19492(12) 0.89623(9) 0.42719(11) 0.0401(3) Uani 1 1 d . . . . .
C28 C 0.24768(15) 0.97333(10) 0.38727(12) 0.0503(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.89(3) . ?
O1 C1 1.3613(18) . ?
N1 H1A 0.98(2) . ?
N1 C8 1.5014(19) . ?
N1 C9 1.4848(17) . ?
N1 C12 1.4912(17) . ?
C1 C2 1.402(2) . ?
C1 C6 1.377(2) . ?
O2 C2 1.3688(19) . ?
O2 C7 1.420(2) . ?
N2 H2 0.919(19) . ?
N2 C10 1.5074(16) . ?
N2 C11 1.5037(17) . ?
N2 C13 1.5309(18) . ?
C2 C3 1.388(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.393(2) . ?
C4 C5 1.388(2) . ?
C4 C8 1.508(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.396(2) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.511(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.507(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13 0.9800 . ?
C13 C14 1.5280(19) . ?
C13 C18 1.528(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.5245(19) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.5306(19) . ?
C16 H16 0.9800 . ?
C16 H16A 0.9800 . ?
C16 C17 1.537(2) . ?
C16 C19A 1.577(9) . ?
C16 C19 1.38(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.525(2) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19A C20A 1.391(6) . ?
C19A C24A 1.374(12) . ?
C19 C20 1.371(15) . ?
C19 C24 1.42(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.407(13) . ?
C20A H20A 0.9300 . ?
C20A C21A 1.383(6) . ?
C21A H21A 0.9300 . ?
C21A C22A 1.382(6) . ?
C21 H21 0.9300 . ?
C21 C22 1.391(13) . ?
C22 H22 0.9300 . ?
C22 C23 1.352(12) . ?
C22A H22A 0.9300 . ?
C22A C23A 1.376(5) . ?
C23A H23A 0.9300 . ?
C23A C24A 1.397(7) . ?
C23 H23 0.9300 . ?
C23 C24 1.385(17) . ?
C24 H24 0.9300 . ?
C24A H24A 0.9300 . ?
F1 C26 1.336(2) . ?
F2 C26 1.3148(18) . ?
F3 C26 1.3330(19) . ?
O3 C25 1.2349(17) . ?
O4 C25 1.2452(16) . ?
C25 C26 1.545(2) . ?
F4 C28 1.315(2) . ?
F5 C28 1.342(2) . ?
O5 C27 1.2470(19) . ?
F6 C28 1.313(2) . ?
O6 C27 1.227(2) . ?
C27 C28 1.542(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 H1 111.5(16) . . ?
C8 N1 H1A 111.3(12) . . ?
C9 N1 H1A 108.8(11) . . ?
C9 N1 C8 112.62(11) . . ?
C9 N1 C12 108.21(10) . . ?
C12 N1 H1A 105.4(12) . . ?
C12 N1 C8 110.21(11) . . ?
O1 C1 C2 121.57(14) . . ?
O1 C1 C6 118.97(13) . . ?
C6 C1 C2 119.47(14) . . ?
C2 O2 C7 117.99(13) . . ?
C10 N2 H2 106.7(11) . . ?
C10 N2 C13 110.49(10) . . ?
C11 N2 H2 108.0(11) . . ?
C11 N2 C10 109.82(10) . . ?
C11 N2 C13 110.01(10) . . ?
C13 N2 H2 111.7(11) . . ?
O2 C2 C1 114.10(13) . . ?
O2 C2 C3 126.06(13) . . ?
C3 C2 C1 119.84(14) . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.58(13) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C8 119.58(13) . . ?
C5 C4 C3 119.32(14) . . ?
C5 C4 C8 120.90(14) . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.11(15) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 120.66(14) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
O2 C7 H7A 109.5 . . ?
O2 C7 H7B 109.5 . . ?
O2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 C4 114.22(11) . . ?
N1 C8 H8A 108.7 . . ?
N1 C8 H8B 108.7 . . ?
C4 C8 H8A 108.7 . . ?
C4 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 C10 110.60(11) . . ?
H9A C9 H9B 108.1 . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
N2 C10 C9 112.76(11) . . ?
N2 C10 H10A 109.0 . . ?
N2 C10 H10B 109.0 . . ?
C9 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
N2 C11 H11A 109.0 . . ?
N2 C11 H11B 109.0 . . ?
N2 C11 C12 112.79(11) . . ?
H11A C11 H11B 107.8 . . ?
C12 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
N1 C12 C11 111.10(11) . . ?
N1 C12 H12A 109.4 . . ?
N1 C12 H12B 109.4 . . ?
C11 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
N2 C13 H13 107.9 . . ?
C14 C13 N2 111.72(11) . . ?
C14 C13 H13 107.9 . . ?
C18 C13 N2 112.03(11) . . ?
C18 C13 H13 107.9 . . ?
C18 C13 C14 109.21(12) . . ?
C13 C14 H14A 109.1 . . ?
C13 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
C15 C14 C13 112.65(11) . . ?
C15 C14 H14A 109.1 . . ?
C15 C14 H14B 109.1 . . ?
C14 C15 H15A 109.3 . . ?
C14 C15 H15B 109.3 . . ?
C14 C15 C16 111.71(12) . . ?
H15A C15 H15B 107.9 . . ?
C16 C15 H15A 109.3 . . ?
C16 C15 H15B 109.3 . . ?
C15 C16 H16 105.5 . . ?
C15 C16 H16A 108.4 . . ?
C15 C16 C17 109.59(11) . . ?
C15 C16 C19A 110.0(4) . . ?
C17 C16 H16 105.5 . . ?
C17 C16 H16A 108.4 . . ?
C17 C16 C19A 111.8(4) . . ?
C19A C16 H16A 108.4 . . ?
C19 C16 C15 119.7(10) . . ?
C19 C16 H16 105.5 . . ?
C19 C16 C17 110.0(11) . . ?
C16 C17 H17A 109.4 . . ?
C16 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C18 C17 C16 111.29(12) . . ?
C18 C17 H17A 109.4 . . ?
C18 C17 H17B 109.4 . . ?
C13 C18 H18A 108.9 . . ?
C13 C18 H18B 108.9 . . ?
C17 C18 C13 113.29(11) . . ?
C17 C18 H18A 108.9 . . ?
C17 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
C20A C19A C16 122.3(7) . . ?
C24A C19A C16 118.9(5) . . ?
C24A C19A C20A 118.7(7) . . ?
C16 C19 C24 125.3(13) . . ?
C20 C19 C16 119.2(18) . . ?
C20 C19 C24 115.4(17) . . ?
C19 C20 H20 118.5 . . ?
C19 C20 C21 123.1(13) . . ?
C21 C20 H20 118.5 . . ?
C19A C20A H20A 119.6 . . ?
C21A C20A C19A 120.7(5) . . ?
C21A C20A H20A 119.6 . . ?
C20A C21A H21A 119.9 . . ?
C22A C21A C20A 120.2(4) . . ?
C22A C21A H21A 119.9 . . ?
C20 C21 H21 120.7 . . ?
C22 C21 C20 118.6(9) . . ?
C22 C21 H21 120.7 . . ?
C21 C22 H22 119.8 . . ?
C23 C22 C21 120.4(10) . . ?
C23 C22 H22 119.8 . . ?
C21A C22A H22A 120.3 . . ?
C23A C22A C21A 119.4(4) . . ?
C23A C22A H22A 120.3 . . ?
C22A C23A H23A 119.9 . . ?
C22A C23A C24A 120.3(5) . . ?
C24A C23A H23A 119.9 . . ?
C22 C23 H23 120.0 . . ?
C22 C23 C24 120.1(10) . . ?
C24 C23 H23 120.0 . . ?
C19 C24 H24 118.8 . . ?
C23 C24 C19 122.4(11) . . ?
C23 C24 H24 118.8 . . ?
C19A C24A C23A 120.6(5) . . ?
C19A C24A H24A 119.7 . . ?
C23A C24A H24A 119.7 . . ?
O3 C25 O4 128.82(13) . . ?
O3 C25 C26 116.12(12) . . ?
O4 C25 C26 115.04(12) . . ?
F1 C26 C25 113.00(13) . . ?
F2 C26 F1 106.71(14) . . ?
F2 C26 F3 107.46(14) . . ?
F2 C26 C25 113.39(12) . . ?
F3 C26 F1 105.53(13) . . ?
F3 C26 C25 110.29(12) . . ?
O5 C27 C28 112.22(14) . . ?
O6 C27 O5 130.01(15) . . ?
O6 C27 C28 117.77(14) . . ?
F4 C28 F5 106.00(16) . . ?
F4 C28 C27 113.59(15) . . ?
F5 C28 C27 110.10(14) . . ?
F6 C28 F4 107.52(16) . . ?
F6 C28 F5 105.94(16) . . ?
F6 C28 C27 113.16(13) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Vapour deposition'
_chemical_compound_source        synthesis
