#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/07/2230739.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2230739
loop_
_publ_author_name
'Shahani, Tara'
'Fun, Hoong-Kun'
'Vijayakumar, V.'
'Ragavan, R. Venkat'
'Sarveswari, S.'
_publ_section_title
;
 4-{[5-(4-Chlorophenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]carbonyl}-N-ethylpiperazine-1-carboxamide
;
_journal_coeditor_code           IS2729
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1747
_journal_page_last               o1748
_journal_paper_doi               10.1107/S1600536811023178
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C23 H23 Cl F N5 O2'
_chemical_formula_moiety         'C23 H23 Cl F N5 O2'
_chemical_formula_sum            'C23 H23 Cl F N5 O2'
_chemical_formula_weight         455.91
_chemical_name_systematic
;
4-{[5-(4-Chlorophenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]carbonyl}-
N-ethylpiperazine-1-carboxamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.5250(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   25.8566(6)
_cell_length_b                   10.0475(2)
_cell_length_c                   16.8822(4)
_cell_measurement_reflns_used    9922
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.81
_cell_measurement_theta_min      2.47
_cell_volume                     4381.64(17)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector
;
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_sigmaI/netI    0.0539
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            59628
_diffrn_reflns_theta_full        32.54
_diffrn_reflns_theta_max         32.54
_diffrn_reflns_theta_min         1.58
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_T_max  0.9781
_exptl_absorpt_correction_T_min  0.8842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1904
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.478
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     587
_refine_ls_number_reflns         15831
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0513
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0548P)²+0.7011P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1170
_refine_ls_wR_factor_ref         0.1355
_reflns_number_gt                10263
_reflns_number_total             15831
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2729.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2230739
_cod_database_fobs_code          2230739
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1A 0.485681(13) 0.77137(4) 0.09217(2) 0.02886(10) Uani d . 1 1 . .
F F1A 0.25759(4) 0.11751(8) 0.15316(6) 0.0340(2) Uani d . 1 1 . .
O O1A -0.05009(4) 0.66568(10) 0.36382(7) 0.0243(2) Uani d . 1 1 . .
O O2A 0.18458(4) 1.01883(10) 0.34187(7) 0.0251(2) Uani d . 1 1 . .
N N1A -0.07036(5) 0.88196(13) 0.38511(9) 0.0273(3) Uani d . 1 1 . .
N N2A 0.01494(4) 0.81812(11) 0.36518(8) 0.0200(3) Uani d . 1 1 . .
N N3A 0.11718(4) 0.87662(11) 0.32283(7) 0.0192(2) Uani d . 1 1 . .
N N4A 0.20253(4) 0.67945(11) 0.28401(7) 0.0178(2) Uani d . 1 1 . .
N N5A 0.24665(4) 0.64098(11) 0.24928(7) 0.0163(2) Uani d . 1 1 . .
C C1A -0.14100(6) 0.85245(18) 0.47714(11) 0.0347(4) Uani d . 1 1 . .
H H1AA -0.1773 0.8340 0.4792 0.052 Uiso calc R 1 1 . .
H H1AB -0.1337 0.9378 0.5006 0.052 Uiso calc R 1 1 . .
H H1AC -0.1217 0.7850 0.5059 0.052 Uiso calc R 1 1 . .
C C2A -0.12569(5) 0.85332(15) 0.39189(11) 0.0269(3) Uani d . 1 1 . .
H H2AA -0.1335 0.7673 0.3682 0.032 Uiso calc R 1 1 . .
H H2AB -0.1459 0.9200 0.3628 0.032 Uiso calc R 1 1 . .
C C3A -0.03604(5) 0.78331(14) 0.37212(9) 0.0199(3) Uani d . 1 1 . .
C C4A 0.03840(5) 0.94481(14) 0.38959(9) 0.0213(3) Uani d . 1 1 . .
H H4AA 0.0538 0.9367 0.4428 0.026 Uiso calc R 1 1 . .
H H4AB 0.0120 1.0133 0.3901 0.026 Uiso calc R 1 1 . .
C C5A 0.07963(5) 0.98407(14) 0.33283(9) 0.0214(3) Uani d . 1 1 . .
H H5AA 0.0633 1.0061 0.2817 0.026 Uiso calc R 1 1 . .
H H5AB 0.0976 1.0627 0.3529 0.026 Uiso calc R 1 1 . .
C C6A 0.09284(5) 0.75057(14) 0.29914(10) 0.0241(3) Uani d . 1 1 . .
H H6AA 0.1190 0.6815 0.2973 0.029 Uiso calc R 1 1 . .
H H6AB 0.0765 0.7593 0.2466 0.029 Uiso calc R 1 1 . .
C C7A 0.05269(5) 0.71207(14) 0.35762(10) 0.0226(3) Uani d . 1 1 . .
H H7AA 0.0352 0.6314 0.3397 0.027 Uiso calc R 1 1 . .
H H7AB 0.0696 0.6944 0.4090 0.027 Uiso calc R 1 1 . .
C C8A 0.16832(5) 0.90795(14) 0.32237(9) 0.0184(3) Uani d . 1 1 . .
C C9A 0.20718(5) 0.81132(13) 0.29278(8) 0.0170(3) Uani d . 1 1 . .
C C10A 0.25417(5) 0.85743(13) 0.26447(8) 0.0175(3) Uani d . 1 1 . .
H H10A 0.2663 0.9446 0.2651 0.021 Uiso calc R 1 1 . .
C C11A 0.27861(5) 0.74722(13) 0.23560(8) 0.0164(3) Uani d . 1 1 . .
C C12A 0.32866(5) 0.74362(13) 0.19775(8) 0.0163(3) Uani d . 1 1 . .
C C13A 0.34136(5) 0.85261(14) 0.15072(9) 0.0187(3) Uani d . 1 1 . .
H H13A 0.3173 0.9203 0.1418 0.022 Uiso calc R 1 1 . .
C C14A 0.38934(5) 0.86114(14) 0.11718(9) 0.0208(3) Uani d . 1 1 . .
H H14A 0.3976 0.9338 0.0861 0.025 Uiso calc R 1 1 . .
C C15A 0.42450(5) 0.75968(14) 0.13092(9) 0.0201(3) Uani d . 1 1 . .
C C16A 0.41256(5) 0.64847(14) 0.17533(9) 0.0198(3) Uani d . 1 1 . .
H H16A 0.4364 0.5797 0.1824 0.024 Uiso calc R 1 1 . .
C C17A 0.36479(5) 0.64093(14) 0.20901(9) 0.0183(3) Uani d . 1 1 . .
H H17A 0.3567 0.5671 0.2393 0.022 Uiso calc R 1 1 . .
C C18A 0.25064(5) 0.50560(13) 0.22406(9) 0.0171(3) Uani d . 1 1 . .
C C19A 0.26649(5) 0.47606(14) 0.14866(9) 0.0196(3) Uani d . 1 1 . .
H H19A 0.2749 0.5441 0.1141 0.023 Uiso calc R 1 1 . .
C C20A 0.26974(5) 0.34438(14) 0.12526(9) 0.0232(3) Uani d . 1 1 . .
H H20A 0.2813 0.3223 0.0756 0.028 Uiso calc R 1 1 . .
C C21A 0.25541(6) 0.24670(14) 0.17733(10) 0.0234(3) Uani d . 1 1 . .
C C22A 0.23838(6) 0.27372(14) 0.25165(10) 0.0247(3) Uani d . 1 1 . .
H H22A 0.2284 0.2055 0.2849 0.030 Uiso calc R 1 1 . .
C C23A 0.23647(5) 0.40536(14) 0.27559(9) 0.0216(3) Uani d . 1 1 . .
H H23A 0.2258 0.4266 0.3259 0.026 Uiso calc R 1 1 . .
Cl Cl1B 0.422665(14) 0.26664(4) 0.22949(3) 0.03439(11) Uani d . 1 1 . .
F F1B 0.60085(4) 0.86517(8) 0.01124(6) 0.0326(2) Uani d . 1 1 . .
O O1B 0.94076(4) 0.32975(9) -0.08019(6) 0.0230(2) Uani d . 1 1 . .
O O2B 0.73926(4) -0.04416(9) 0.03639(6) 0.0237(2) Uani d . 1 1 . .
N N1B 0.96352(4) 0.11287(13) -0.08865(8) 0.0213(3) Uani d . 1 1 . .
N N2B 0.87671(4) 0.17620(12) -0.10070(8) 0.0222(3) Uani d . 1 1 . .
N N3B 0.79447(4) 0.11579(11) -0.00106(8) 0.0199(3) Uani d . 1 1 . .
N N5B 0.70497(4) 0.30083(11) 0.02996(7) 0.0174(2) Uani d . 1 1 . .
N N6B 0.65872(4) 0.34179(11) 0.05624(7) 0.0167(2) Uani d . 1 1 . .
C C1B 1.04218(6) 0.16926(15) -0.16134(10) 0.0271(3) Uani d . 1 1 . .
H H1BA 1.0786 0.1863 -0.1533 0.041 Uiso calc R 1 1 . .
H H1BB 1.0257 0.2451 -0.1861 0.041 Uiso calc R 1 1 . .
H H1BC 1.0371 0.0927 -0.1948 0.041 Uiso calc R 1 1 . .
C C2B 1.01871(5) 0.14349(15) -0.08203(10) 0.0235(3) Uani d . 1 1 . .
H H2BA 1.0368 0.0697 -0.0562 0.028 Uiso calc R 1 1 . .
H H2BB 1.0239 0.2214 -0.0487 0.028 Uiso calc R 1 1 . .
C C3B 0.92797(5) 0.21163(14) -0.08898(9) 0.0182(3) Uani d . 1 1 . .
C C4B 0.85644(5) 0.04105(14) -0.09711(10) 0.0228(3) Uani d . 1 1 . .
H H4BA 0.8841 -0.0219 -0.1053 0.027 Uiso calc R 1 1 . .
H H4BB 0.8301 0.0285 -0.1392 0.027 Uiso calc R 1 1 . .
C C5B 0.83335(5) 0.01433(14) -0.01783(10) 0.0229(3) Uani d . 1 1 . .
H H5BA 0.8174 -0.0730 -0.0185 0.028 Uiso calc R 1 1 . .
H H5BB 0.8605 0.0152 0.0236 0.028 Uiso calc R 1 1 . .
C C6B 0.81405(5) 0.25202(13) -0.00562(9) 0.0196(3) Uani d . 1 1 . .
H H6BA 0.8405 0.2667 0.0361 0.024 Uiso calc R 1 1 . .
H H6BB 0.7861 0.3146 0.0018 0.024 Uiso calc R 1 1 . .
C C7B 0.83678(5) 0.27468(14) -0.08610(9) 0.0220(3) Uani d . 1 1 . .
H H7BA 0.8095 0.2687 -0.1273 0.026 Uiso calc R 1 1 . .
H H7BB 0.8516 0.3633 -0.0879 0.026 Uiso calc R 1 1 . .
C C8B 0.74869(5) 0.07474(14) 0.02659(8) 0.0180(3) Uani d . 1 1 . .
C C9B 0.70686(5) 0.17059(13) 0.04625(8) 0.0166(3) Uani d . 1 1 . .
C C10B 0.66187(5) 0.12823(13) 0.08232(8) 0.0174(3) Uani d . 1 1 . .
H H10B 0.6543 0.0423 0.0988 0.021 Uiso calc R 1 1 . .
C C11B 0.63125(5) 0.23920(13) 0.08848(8) 0.0161(3) Uani d . 1 1 . .
C C12B 0.58012(5) 0.25153(13) 0.12242(8) 0.0166(3) Uani d . 1 1 . .
C C13B 0.54518(5) 0.14584(14) 0.11289(9) 0.0193(3) Uani d . 1 1 . .
H H13B 0.5544 0.0715 0.0839 0.023 Uiso calc R 1 1 . .
C C14B 0.49710(5) 0.14973(15) 0.14575(9) 0.0220(3) Uani d . 1 1 . .
H H14B 0.4742 0.0789 0.1388 0.026 Uiso calc R 1 1 . .
C C15B 0.48342(5) 0.26067(15) 0.18924(9) 0.0218(3) Uani d . 1 1 . .
C C16B 0.51731(5) 0.36627(14) 0.20055(9) 0.0208(3) Uani d . 1 1 . .
H H16B 0.5079 0.4397 0.2302 0.025 Uiso calc R 1 1 . .
C C17B 0.56554(5) 0.36181(14) 0.16724(8) 0.0186(3) Uani d . 1 1 . .
H H17B 0.5884 0.4327 0.1748 0.022 Uiso calc R 1 1 . .
C C18B 0.64400(5) 0.47767(13) 0.04455(8) 0.0173(3) Uani d . 1 1 . .
C C19B 0.59651(5) 0.50670(14) 0.00656(8) 0.0192(3) Uani d . 1 1 . .
H H19B 0.5747 0.4383 -0.0111 0.023 Uiso calc R 1 1 . .
C C20B 0.58200(6) 0.63773(14) -0.00470(9) 0.0210(3) Uani d . 1 1 . .
H H20B 0.5504 0.6593 -0.0300 0.025 Uiso calc R 1 1 . .
C C21B 0.61547(6) 0.73578(14) 0.02250(9) 0.0222(3) Uani d . 1 1 . .
C C22B 0.66303(6) 0.71025(14) 0.05946(10) 0.0234(3) Uani d . 1 1 . .
H H22B 0.6848 0.7793 0.0764 0.028 Uiso calc R 1 1 . .
C C23B 0.67749(5) 0.57786(14) 0.07056(9) 0.0211(3) Uani d . 1 1 . .
H H23B 0.7093 0.5568 0.0952 0.025 Uiso calc R 1 1 . .
H H1NB 0.9560(7) 0.0304(19) -0.1012(11) 0.037(5) Uiso d . 1 1 . .
H H1NA -0.0598(6) 0.9674(18) 0.3909(11) 0.031(5) Uiso d . 1 1 . .
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3A N1A C2A . . 121.10(12) ?
C3A N1A H1NA . . 120.9(10) ?
C2A N1A H1NA . . 118.0(10) ?
C3A N2A C7A . . 118.12(11) ?
C3A N2A C4A . . 125.84(11) ?
C7A N2A C4A . . 113.01(11) ?
C8A N3A C6A . . 127.31(11) ?
C8A N3A C5A . . 118.63(11) ?
C6A N3A C5A . . 112.94(11) ?
C9A N4A N5A . . 104.83(10) ?
N4A N5A C11A . . 111.89(10) ?
N4A N5A C18A . . 118.09(10) ?
C11A N5A C18A . . 129.52(11) ?
C2A C1A H1AA . . 109.5 ?
C2A C1A H1AB . . 109.5 ?
H1AA C1A H1AB . . 109.5 ?
C2A C1A H1AC . . 109.5 ?
H1AA C1A H1AC . . 109.5 ?
H1AB C1A H1AC . . 109.5 ?
N1A C2A C1A . . 111.88(14) ?
N1A C2A H2AA . . 109.2 ?
C1A C2A H2AA . . 109.2 ?
N1A C2A H2AB . . 109.2 ?
C1A C2A H2AB . . 109.2 ?
H2AA C2A H2AB . . 107.9 ?
O1A C3A N1A . . 121.59(13) ?
O1A C3A N2A . . 120.62(12) ?
N1A C3A N2A . . 117.73(12) ?
N2A C4A C5A . . 110.06(12) ?
N2A C4A H4AA . . 109.6 ?
C5A C4A H4AA . . 109.6 ?
N2A C4A H4AB . . 109.6 ?
C5A C4A H4AB . . 109.6 ?
H4AA C4A H4AB . . 108.2 ?
N3A C5A C4A . . 111.63(11) ?
N3A C5A H5AA . . 109.3 ?
C4A C5A H5AA . . 109.3 ?
N3A C5A H5AB . . 109.3 ?
C4A C5A H5AB . . 109.3 ?
H5AA C5A H5AB . . 108.0 ?
N3A C6A C7A . . 110.01(12) ?
N3A C6A H6AA . . 109.7 ?
C7A C6A H6AA . . 109.7 ?
N3A C6A H6AB . . 109.7 ?
C7A C6A H6AB . . 109.7 ?
H6AA C6A H6AB . . 108.2 ?
N2A C7A C6A . . 110.62(12) ?
N2A C7A H7AA . . 109.5 ?
C6A C7A H7AA . . 109.5 ?
N2A C7A H7AB . . 109.5 ?
C6A C7A H7AB . . 109.5 ?
H7AA C7A H7AB . . 108.1 ?
O2A C8A N3A . . 121.94(12) ?
O2A C8A C9A . . 116.71(12) ?
N3A C8A C9A . . 121.23(12) ?
N4A C9A C10A . . 111.35(12) ?
N4A C9A C8A . . 128.32(12) ?
C10A C9A C8A . . 120.18(12) ?
C11A C10A C9A . . 105.85(12) ?
C11A C10A H10A . . 127.1 ?
C9A C10A H10A . . 127.1 ?
C10A C11A N5A . . 106.06(11) ?
C10A C11A C12A . . 126.99(12) ?
N5A C11A C12A . . 126.95(12) ?
C17A C12A C13A . . 118.81(12) ?
C17A C12A C11A . . 123.71(12) ?
C13A C12A C11A . . 117.43(12) ?
C14A C13A C12A . . 121.02(13) ?
C14A C13A H13A . . 119.5 ?
C12A C13A H13A . . 119.5 ?
C15A C14A C13A . . 118.70(13) ?
C15A C14A H14A . . 120.7 ?
C13A C14A H14A . . 120.7 ?
C14A C15A C16A . . 121.69(13) ?
C14A C15A Cl1A . . 119.34(11) ?
C16A C15A Cl1A . . 118.97(11) ?
C17A C16A C15A . . 119.32(13) ?
C17A C16A H16A . . 120.3 ?
C15A C16A H16A . . 120.3 ?
C16A C17A C12A . . 120.42(13) ?
C16A C17A H17A . . 119.8 ?
C12A C17A H17A . . 119.8 ?
C19A C18A C23A . . 121.06(13) ?
C19A C18A N5A . . 120.32(12) ?
C23A C18A N5A . . 118.57(13) ?
C20A C19A C18A . . 119.38(13) ?
C20A C19A H19A . . 120.3 ?
C18A C19A H19A . . 120.3 ?
C21A C20A C19A . . 118.48(14) ?
C21A C20A H20A . . 120.8 ?
C19A C20A H20A . . 120.8 ?
F1A C21A C22A . . 118.73(13) ?
F1A C21A C20A . . 118.11(14) ?
C22A C21A C20A . . 123.16(13) ?
C21A C22A C23A . . 118.17(14) ?
C21A C22A H22A . . 120.9 ?
C23A C22A H22A . . 120.9 ?
C22A C23A C18A . . 119.71(14) ?
C22A C23A H23A . . 120.1 ?
C18A C23A H23A . . 120.1 ?
C3B N1B C2B . . 120.51(12) ?
C3B N1B H1NB . . 123.3(12) ?
C2B N1B H1NB . . 115.2(11) ?
C3B N2B C4B . . 125.43(12) ?
C3B N2B C7B . . 118.94(12) ?
C4B N2B C7B . . 111.50(11) ?
C8B N3B C6B . . 127.76(11) ?
C8B N3B C5B . . 118.09(11) ?
C6B N3B C5B . . 113.46(11) ?
C9B N5B N6B . . 104.71(10) ?
N5B N6B C11B . . 112.29(10) ?
N5B N6B C18B . . 118.53(10) ?
C11B N6B C18B . . 129.11(11) ?
C2B C1B H1BA . . 109.5 ?
C2B C1B H1BB . . 109.5 ?
H1BA C1B H1BB . . 109.5 ?
C2B C1B H1BC . . 109.5 ?
H1BA C1B H1BC . . 109.5 ?
H1BB C1B H1BC . . 109.5 ?
N1B C2B C1B . . 113.35(13) ?
N1B C2B H2BA . . 108.9 ?
C1B C2B H2BA . . 108.9 ?
N1B C2B H2BB . . 108.9 ?
C1B C2B H2BB . . 108.9 ?
H2BA C2B H2BB . . 107.7 ?
O1B C3B N1B . . 121.64(13) ?
O1B C3B N2B . . 120.95(12) ?
N1B C3B N2B . . 117.40(12) ?
N2B C4B C5B . . 111.00(12) ?
N2B C4B H4BA . . 109.4 ?
C5B C4B H4BA . . 109.4 ?
N2B C4B H4BB . . 109.4 ?
C5B C4B H4BB . . 109.4 ?
H4BA C4B H4BB . . 108.0 ?
N3B C5B C4B . . 110.34(12) ?
N3B C5B H5BA . . 109.6 ?
C4B C5B H5BA . . 109.6 ?
N3B C5B H5BB . . 109.6 ?
C4B C5B H5BB . . 109.6 ?
H5BA C5B H5BB . . 108.1 ?
N3B C6B C7B . . 109.60(11) ?
N3B C6B H6BA . . 109.8 ?
C7B C6B H6BA . . 109.8 ?
N3B C6B H6BB . . 109.8 ?
C7B C6B H6BB . . 109.8 ?
H6BA C6B H6BB . . 108.2 ?
N2B C7B C6B . . 110.71(12) ?
N2B C7B H7BA . . 109.5 ?
C6B C7B H7BA . . 109.5 ?
N2B C7B H7BB . . 109.5 ?
C6B C7B H7BB . . 109.5 ?
H7BA C7B H7BB . . 108.1 ?
O2B C8B N3B . . 121.49(12) ?
O2B C8B C9B . . 116.42(12) ?
N3B C8B C9B . . 122.09(12) ?
N5B C9B C10B . . 111.27(11) ?
N5B C9B C8B . . 127.16(12) ?
C10B C9B C8B . . 121.49(12) ?
C11B C10B C9B . . 106.16(12) ?
C11B C10B H10B . . 126.9 ?
C9B C10B H10B . . 126.9 ?
C10B C11B N6B . . 105.56(11) ?
C10B C11B C12B . . 129.01(12) ?
N6B C11B C12B . . 125.42(12) ?
C13B C12B C17B . . 118.31(12) ?
C13B C12B C11B . . 118.60(12) ?
C17B C12B C11B . . 123.02(12) ?
C14B C13B C12B . . 121.29(13) ?
C14B C13B H13B . . 119.4 ?
C12B C13B H13B . . 119.4 ?
C13B C14B C15B . . 119.26(13) ?
C13B C14B H14B . . 120.4 ?
C15B C14B H14B . . 120.4 ?
C16B C15B C14B . . 120.90(13) ?
C16B C15B Cl1B . . 119.79(11) ?
C14B C15B Cl1B . . 119.30(11) ?
C15B C16B C17B . . 119.54(13) ?
C15B C16B H16B . . 120.2 ?
C17B C16B H16B . . 120.2 ?
C16B C17B C12B . . 120.70(13) ?
C16B C17B H17B . . 119.6 ?
C12B C17B H17B . . 119.6 ?
C23B C18B C19B . . 121.34(13) ?
C23B C18B N6B . . 119.42(12) ?
C19B C18B N6B . . 119.24(12) ?
C20B C19B C18B . . 119.52(13) ?
C20B C19B H19B . . 120.2 ?
C18B C19B H19B . . 120.2 ?
C21B C20B C19B . . 118.27(13) ?
C21B C20B H20B . . 120.9 ?
C19B C20B H20B . . 120.9 ?
F1B C21B C20B . . 117.97(13) ?
F1B C21B C22B . . 118.45(13) ?
C20B C21B C22B . . 123.57(13) ?
C21B C22B C23B . . 117.88(13) ?
C21B C22B H22B . . 121.1 ?
C23B C22B H22B . . 121.1 ?
C18B C23B C22B . . 119.40(13) ?
C18B C23B H23B . . 120.3 ?
C22B C23B H23B . . 120.3 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1A C15A . 1.7422(14) ?
F1A C21A . 1.3626(16) ?
O1A C3A . 1.2426(16) ?
O2A C8A . 1.2305(16) ?
N1A C3A . 1.3546(18) ?
N1A C2A . 1.4687(18) ?
N1A H1NA . 0.905(18) ?
N2A C3A . 1.3737(17) ?
N2A C7A . 1.4545(17) ?
N2A C4A . 1.4616(18) ?
N3A C8A . 1.3594(17) ?
N3A C6A . 1.4622(18) ?
N3A C5A . 1.4668(17) ?
N4A C9A . 1.3380(17) ?
N4A N5A . 1.3616(15) ?
N5A C11A . 1.3757(16) ?
N5A C18A . 1.4304(17) ?
C1A C2A . 1.510(2) ?
C1A H1AA . 0.9600 ?
C1A H1AB . 0.9600 ?
C1A H1AC . 0.9600 ?
C2A H2AA . 0.9700 ?
C2A H2AB . 0.9700 ?
C4A C5A . 1.517(2) ?
C4A H4AA . 0.9700 ?
C4A H4AB . 0.9700 ?
C5A H5AA . 0.9700 ?
C5A H5AB . 0.9700 ?
C6A C7A . 1.514(2) ?
C6A H6AA . 0.9700 ?
C6A H6AB . 0.9700 ?
C7A H7AA . 0.9700 ?
C7A H7AB . 0.9700 ?
C8A C9A . 1.4987(19) ?
C9A C10A . 1.4039(18) ?
C10A C11A . 1.3747(18) ?
C10A H10A . 0.9300 ?
C11A C12A . 1.4687(18) ?
C12A C17A . 1.3992(18) ?
C12A C13A . 1.4003(19) ?
C13A C14A . 1.3887(19) ?
C13A H13A . 0.9300 ?
C14A C15A . 1.379(2) ?
C14A H14A . 0.9300 ?
C15A C16A . 1.388(2) ?
C16A C17A . 1.3844(19) ?
C16A H16A . 0.9300 ?
C17A H17A . 0.9300 ?
C18A C19A . 1.387(2) ?
C18A C23A . 1.390(2) ?
C19A C20A . 1.384(2) ?
C19A H19A . 0.9300 ?
C20A C21A . 1.379(2) ?
C20A H20A . 0.9300 ?
C21A C22A . 1.375(2) ?
C22A C23A . 1.384(2) ?
C22A H22A . 0.9300 ?
C23A H23A . 0.9300 ?
Cl1B C15B . 1.7398(14) ?
F1B C21B . 1.3648(16) ?
O1B C3B . 1.2391(16) ?
O2B C8B . 1.2320(16) ?
N1B C3B . 1.3524(18) ?
N1B C2B . 1.4594(18) ?
N1B H1NB . 0.876(18) ?
N2B C3B . 1.3783(18) ?
N2B C4B . 1.4578(18) ?
N2B C7B . 1.4587(17) ?
N3B C8B . 1.3556(17) ?
N3B C6B . 1.4626(17) ?
N3B C5B . 1.4681(17) ?
N5B C9B . 1.3377(17) ?
N5B N6B . 1.3577(15) ?
N6B C11B . 1.3775(16) ?
N6B C18B . 1.4287(17) ?
C1B C2B . 1.516(2) ?
C1B H1BA . 0.9600 ?
C1B H1BB . 0.9600 ?
C1B H1BC . 0.9600 ?
C2B H2BA . 0.9700 ?
C2B H2BB . 0.9700 ?
C4B C5B . 1.513(2) ?
C4B H4BA . 0.9700 ?
C4B H4BB . 0.9700 ?
C5B H5BA . 0.9700 ?
C5B H5BB . 0.9700 ?
C6B C7B . 1.521(2) ?
C6B H6BA . 0.9700 ?
C6B H6BB . 0.9700 ?
C7B H7BA . 0.9700 ?
C7B H7BB . 0.9700 ?
C8B C9B . 1.4965(19) ?
C9B C10B . 1.4026(18) ?
C10B C11B . 1.3742(18) ?
C10B H10B . 0.9300 ?
C11B C12B . 1.4691(19) ?
C12B C13B . 1.3989(19) ?
C12B C17B . 1.4026(19) ?
C13B C14B . 1.3840(19) ?
C13B H13B . 0.9300 ?
C14B C15B . 1.389(2) ?
C14B H14B . 0.9300 ?
C15B C16B . 1.384(2) ?
C16B C17B . 1.3909(19) ?
C16B H16B . 0.9300 ?
C17B H17B . 0.9300 ?
C18B C23B . 1.3864(19) ?
C18B C19B . 1.3909(19) ?
C19B C20B . 1.3798(19) ?
C19B H19B . 0.9300 ?
C20B C21B . 1.377(2) ?
C20B H20B . 0.9300 ?
C21B C22B . 1.378(2) ?
C22B C23B . 1.392(2) ?
C22B H22B . 0.9300 ?
C23B H23B . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1B H1NB O1A 4_665 0.876(18) 2.060(19) 2.9284(16) 171.1(16) yes
N1A H1NA O1B 4_476 0.905(18) 2.096(18) 2.9667(16) 161.1(15) yes
C4A H4AA O1B 2_655 0.97 2.55 3.4393(19) 152 yes
C4A H4AB O1B 4_476 0.97 2.49 3.4466(17) 168 yes
C6A H6AA N4A . 0.97 2.18 2.9468(17) 135 yes
C13A H13A F1A 1_565 0.93 2.52 3.4330(16) 166 yes
C4B H4BA O1A 4_665 0.97 2.31 3.2757(17) 175 yes
C22A H22A O2A 1_545 0.93 2.41 3.3167(18) 164 yes
C22B H22B O2B 1_565 0.93 2.38 3.1927(18) 146 yes
C23A H23A O2B 2_655 0.93 2.47 3.2482(18) 141 yes
C6B H6BB N5B . 0.97 2.18 2.9505(17) 136 yes
C7B H7BA Cg1 3_665 0.97 2.59 3.5216(16) 162 yes
C2A H2AB Cg4 2_555 0.97 2.95 3.5831(15) 124 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9A N4A N5A C11A . . . . -0.53(15) ?
C9A N4A N5A C18A . . . . -173.20(12) ?
C3A N1A C2A C1A . . . . 101.53(17) ?
C2A N1A C3A O1A . . . . 1.5(2) ?
C2A N1A C3A N2A . . . . 178.95(14) ?
C7A N2A C3A O1A . . . . -7.4(2) ?
C4A N2A C3A O1A . . . . -166.25(14) ?
C7A N2A C3A N1A . . . . 175.14(14) ?
C4A N2A C3A N1A . . . . 16.3(2) ?
C3A N2A C4A C5A . . . . -144.92(14) ?
C7A N2A C4A C5A . . . . 55.31(16) ?
C8A N3A C5A C4A . . . . -137.14(13) ?
C6A N3A C5A C4A . . . . 54.07(17) ?
N2A C4A C5A N3A . . . . -52.52(16) ?
C8A N3A C6A C7A . . . . 137.43(14) ?
C5A N3A C6A C7A . . . . -54.96(16) ?
C3A N2A C7A C6A . . . . 141.13(14) ?
C4A N2A C7A C6A . . . . -57.39(16) ?
N3A C6A C7A N2A . . . . 55.63(16) ?
C6A N3A C8A O2A . . . . 178.21(14) ?
C5A N3A C8A O2A . . . . 11.2(2) ?
C6A N3A C8A C9A . . . . 2.3(2) ?
C5A N3A C8A C9A . . . . -164.64(13) ?
N5A N4A C9A C10A . . . . -0.47(15) ?
N5A N4A C9A C8A . . . . 175.10(14) ?
O2A C8A C9A N4A . . . . 164.53(14) ?
N3A C8A C9A N4A . . . . -19.4(2) ?
O2A C8A C9A C10A . . . . -20.3(2) ?
N3A C8A C9A C10A . . . . 155.83(14) ?
N4A C9A C10A C11A . . . . 1.27(16) ?
C8A C9A C10A C11A . . . . -174.71(13) ?
C9A C10A C11A N5A . . . . -1.50(15) ?
C9A C10A C11A C12A . . . . 178.44(13) ?
N4A N5A C11A C10A . . . . 1.31(15) ?
C18A N5A C11A C10A . . . . 172.92(13) ?
N4A N5A C11A C12A . . . . -178.62(13) ?
C18A N5A C11A C12A . . . . -7.0(2) ?
C10A C11A C12A C17A . . . . 142.40(15) ?
N5A C11A C12A C17A . . . . -37.7(2) ?
C10A C11A C12A C13A . . . . -34.7(2) ?
N5A C11A C12A C13A . . . . 145.25(14) ?
C17A C12A C13A C14A . . . . -1.6(2) ?
C11A C12A C13A C14A . . . . 175.65(13) ?
C12A C13A C14A C15A . . . . 0.1(2) ?
C13A C14A C15A C16A . . . . 1.8(2) ?
C13A C14A C15A Cl1A . . . . -177.81(11) ?
C14A C15A C16A C17A . . . . -2.2(2) ?
Cl1A C15A C16A C17A . . . . 177.41(11) ?
C15A C16A C17A C12A . . . . 0.7(2) ?
C13A C12A C17A C16A . . . . 1.2(2) ?
C11A C12A C17A C16A . . . . -175.88(13) ?
N4A N5A C18A C19A . . . . 131.60(13) ?
C11A N5A C18A C19A . . . . -39.6(2) ?
N4A N5A C18A C23A . . . . -46.05(17) ?
C11A N5A C18A C23A . . . . 142.78(14) ?
C23A C18A C19A C20A . . . . -2.0(2) ?
N5A C18A C19A C20A . . . . -179.56(12) ?
C18A C19A C20A C21A . . . . 2.0(2) ?
C19A C20A C21A F1A . . . . 178.53(13) ?
C19A C20A C21A C22A . . . . -0.5(2) ?
F1A C21A C22A C23A . . . . 179.84(13) ?
C20A C21A C22A C23A . . . . -1.2(2) ?
C21A C22A C23A C18A . . . . 1.2(2) ?
C19A C18A C23A C22A . . . . 0.3(2) ?
N5A C18A C23A C22A . . . . 177.93(13) ?
C9B N5B N6B C11B . . . . -0.35(15) ?
C9B N5B N6B C18B . . . . -177.66(12) ?
C3B N1B C2B C1B . . . . -87.69(17) ?
C2B N1B C3B O1B . . . . -3.3(2) ?
C2B N1B C3B N2B . . . . 175.78(13) ?
C4B N2B C3B O1B . . . . -168.01(14) ?
C7B N2B C3B O1B . . . . -12.9(2) ?
C4B N2B C3B N1B . . . . 12.9(2) ?
C7B N2B C3B N1B . . . . 168.07(13) ?
C3B N2B C4B C5B . . . . 99.49(16) ?
C7B N2B C4B C5B . . . . -57.23(16) ?
C8B N3B C5B C4B . . . . 134.45(13) ?
C6B N3B C5B C4B . . . . -54.31(16) ?
N2B C4B C5B N3B . . . . 54.13(16) ?
C8B N3B C6B C7B . . . . -134.86(14) ?
C5B N3B C6B C7B . . . . 54.92(16) ?
C3B N2B C7B C6B . . . . -100.30(15) ?
C4B N2B C7B C6B . . . . 58.10(16) ?
N3B C6B C7B N2B . . . . -55.80(15) ?
C6B N3B C8B O2B . . . . -170.97(14) ?
C5B N3B C8B O2B . . . . -1.1(2) ?
C6B N3B C8B C9B . . . . 9.5(2) ?
C5B N3B C8B C9B . . . . 179.32(13) ?
N6B N5B C9B C10B . . . . 0.39(15) ?
N6B N5B C9B C8B . . . . 177.27(13) ?
O2B C8B C9B N5B . . . . -169.57(14) ?
N3B C8B C9B N5B . . . . 10.0(2) ?
O2B C8B C9B C10B . . . . 7.0(2) ?
N3B C8B C9B C10B . . . . -173.42(13) ?
N5B C9B C10B C11B . . . . -0.30(16) ?
C8B C9B C10B C11B . . . . -177.38(12) ?
C9B C10B C11B N6B . . . . 0.07(15) ?
C9B C10B C11B C12B . . . . -179.32(14) ?
N5B N6B C11B C10B . . . . 0.17(16) ?
C18B N6B C11B C10B . . . . 177.12(13) ?
N5B N6B C11B C12B . . . . 179.59(13) ?
C18B N6B C11B C12B . . . . -3.5(2) ?
C10B C11B C12B C13B . . . . -35.6(2) ?
N6B C11B C12B C13B . . . . 145.11(14) ?
C10B C11B C12B C17B . . . . 141.27(15) ?
N6B C11B C12B C17B . . . . -38.0(2) ?
C17B C12B C13B C14B . . . . 0.8(2) ?
C11B C12B C13B C14B . . . . 177.84(13) ?
C12B C13B C14B C15B . . . . -0.2(2) ?
C13B C14B C15B C16B . . . . -0.5(2) ?
C13B C14B C15B Cl1B . . . . 179.17(11) ?
C14B C15B C16B C17B . . . . 0.6(2) ?
Cl1B C15B C16B C17B . . . . -179.05(11) ?
C15B C16B C17B C12B . . . . 0.0(2) ?
C13B C12B C17B C16B . . . . -0.7(2) ?
C11B C12B C17B C16B . . . . -177.58(13) ?
N5B N6B C18B C23B . . . . -53.26(18) ?
C11B N6B C18B C23B . . . . 129.96(15) ?
N5B N6B C18B C19B . . . . 126.13(14) ?
C11B N6B C18B C19B . . . . -50.7(2) ?
C23B C18B C19B C20B . . . . -0.8(2) ?
N6B C18B C19B C20B . . . . 179.81(12) ?
C18B C19B C20B C21B . . . . -0.1(2) ?
C19B C20B C21B F1B . . . . -179.93(13) ?
C19B C20B C21B C22B . . . . 0.9(2) ?
F1B C21B C22B C23B . . . . -179.99(13) ?
C20B C21B C22B C23B . . . . -0.8(2) ?
C19B C18B C23B C22B . . . . 0.9(2) ?
N6B C18B C23B C22B . . . . -179.73(13) ?
C21B C22B C23B C18B . . . . -0.1(2) ?
