#------------------------------------------------------------------------------
#$Date: 2020-07-18 00:34:13 +0300 (Sat, 18 Jul 2020) $
#$Revision: 254380 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/08/7240889.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7240889
loop_
_publ_author_name
'Cunha, Micael Rodrigues'
'Bhardwaj, Rajesh'
'Carrel, Aline Lucie'
'Lindinger, Sonja'
'Romanin, Christoph'
'Parise-Filho, Roberto'
'Hediger, Matthias A.'
'Reymond, Jean-Louis'
_publ_section_title
;
 Natural product inspired optimization of a selective TRPV6 calcium
 channel inhibitor
;
_journal_name_full               'RSC Medicinal Chemistry'
_journal_paper_doi               10.1039/D0MD00145G
_journal_year                    2020
_chemical_compound_source        synthesis
_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_name_common            31
_chemical_name_systematic
5-((4-((1s,4s)-4-(3-(trifluoromethyl)phenyl)cyclohexyl)piperazin-1-yl)methyl)pyridin-2(1H)-one
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-04-15 deposited with the CCDC.	2020-06-25 downloaded from the CCDC.
;
_cell_angle_alpha                98.1817(9)
_cell_angle_beta                 92.5946(8)
_cell_angle_gamma                103.5389(8)
_cell_formula_units_Z            2
_cell_length_a                   8.23301(6)
_cell_length_b                   13.02347(14)
_cell_length_c                   13.57687(16)
_cell_measurement_reflns_used    23345
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      76.8250
_cell_measurement_theta_min      3.2950
_cell_volume                     1396.21(3)
_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)'
_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_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_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_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_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_description       prism
_exptl_crystal_F_000             668
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.043
_refine_diff_density_max         0.684
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.052
_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_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0516
_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
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5341
_reflns_number_total             5783
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0md00145g2.cif
_cod_data_source_block           19jlr002b
_cod_original_cell_volume        1396.21(2)
_cod_database_code               7240889
_shelx_shelxl_version_number     2018/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.947
_shelx_estimated_absorpt_t_min   0.731
_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)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
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'
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
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_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_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) . . . . ?
