#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/00/2230011.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_2230011
loop_
_publ_author_name
'Yoon, Yeong Keng'
'Ali, Mohamed Ashraf'
'Choon, Tan Soo'
'Hemamalini, Madhukar'
'Fun, Hoong-Kun'
_publ_section_title
;
 Ethyl
 1-[2-(morpholin-4-yl)ethyl]-2-[4-(trifluoromethyl)phenyl]-1H-benzimidazole-5-carboxylate
;
_journal_coeditor_code           HB5849
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1215
_journal_paper_doi               10.1107/S1600536811014619
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C23 H24 F3 N3 O3'
_chemical_formula_moiety         'C23 H24 F3 N3 O3'
_chemical_formula_sum            'C23 H24 F3 N3 O3'
_chemical_formula_weight         447.45
_chemical_name_systematic
;
Ethyl 1-[2-(morpholin-4-yl)ethyl]-2-[4-(trifluoromethyl)phenyl]-1H-
benzimidazole-5-carboxylate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                96.8680(10)
_cell_angle_beta                 109.6380(10)
_cell_angle_gamma                110.8330(10)
_cell_formula_units_Z            2
_cell_length_a                   10.1463(2)
_cell_length_b                   10.5595(2)
_cell_length_c                   11.5775(2)
_cell_measurement_reflns_used    9996
_cell_measurement_temperature    100.0(10)
_cell_measurement_theta_max      30.12
_cell_measurement_theta_min      2.35
_cell_volume                     1050.83(4)
_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      100.0(10)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_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  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0213
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22546
_diffrn_reflns_theta_full        30.16
_diffrn_reflns_theta_max         30.16
_diffrn_reflns_theta_min         1.94
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.264
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         6122
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0382
_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)+(0.0561P)²+0.2843P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1055
_reflns_number_gt                5266
_reflns_number_total             6122
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5849.cif
_cod_data_source_block           I
_cod_original_cell_volume        1050.83(3)
_cod_database_code               2230011
_cod_database_fobs_code          2230011
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
F F1 0.57861(8) 1.42374(7) 0.30620(7) 0.02777(15) Uani d . 1 1 . .
F F2 0.46917(8) 1.29209(7) 0.11309(6) 0.02950(16) Uani d . 1 1 . .
F F3 0.71291(8) 1.42604(7) 0.19595(7) 0.02843(15) Uani d . 1 1 . .
O O1 0.69592(9) 0.47558(8) 0.74341(7) 0.02040(15) Uani d . 1 1 . .
O O2 0.85918(10) 0.40173(9) 0.69712(8) 0.02932(18) Uani d . 1 1 . .
O O3 1.19661(9) 0.84859(9) 0.01681(7) 0.02600(17) Uani d . 1 1 . .
N N1 0.83537(9) 0.85327(9) 0.38581(8) 0.01618(16) Uani d . 1 1 . .
N N2 0.65751(9) 0.82663(9) 0.46835(8) 0.01700(16) Uani d . 1 1 . .
N N3 0.98967(9) 0.86116(8) 0.13194(7) 0.01548(15) Uani d . 1 1 . .
C C1 0.73153(11) 0.74099(10) 0.50627(9) 0.01619(17) Uani d . 1 1 . .
C C2 0.71070(11) 0.64983(10) 0.58354(9) 0.01726(18) Uani d . 1 1 . .
H H2A 0.6343 0.6359 0.6167 0.021 Uiso calc R 1 1 . .
C C3 0.80658(11) 0.58039(10) 0.60970(9) 0.01745(18) Uani d . 1 1 . .
C C4 0.92137(11) 0.60204(10) 0.56165(9) 0.01902(18) Uani d . 1 1 . .
H H4A 0.9867 0.5550 0.5839 0.023 Uiso calc R 1 1 . .
C C5 0.94156(11) 0.68952(10) 0.48328(9) 0.01836(18) Uani d . 1 1 . .
H H5A 1.0176 0.7028 0.4498 0.022 Uiso calc R 1 1 . .
C C6 0.84348(11) 0.75739(10) 0.45626(9) 0.01645(17) Uani d . 1 1 . .
C C7 0.72211(11) 0.89169(10) 0.39757(9) 0.01597(17) Uani d . 1 1 . .
C C8 0.68579(11) 1.00214(10) 0.34664(9) 0.01626(17) Uani d . 1 1 . .
C C9 0.69019(11) 1.02693(10) 0.23121(9) 0.01882(18) Uani d . 1 1 . .
H H9A 0.7115 0.9671 0.1792 0.023 Uiso calc R 1 1 . .
C C10 0.66367(11) 1.13828(11) 0.19277(9) 0.01912(19) Uani d . 1 1 . .
H H10A 0.6688 1.1559 0.1155 0.023 Uiso calc R 1 1 . .
C C11 0.62940(11) 1.22431(10) 0.26810(9) 0.01741(18) Uani d . 1 1 . .
C C12 0.61869(11) 1.19837(10) 0.38023(9) 0.01806(18) Uani d . 1 1 . .
H H12A 0.5924 1.2558 0.4298 0.022 Uiso calc R 1 1 . .
C C13 0.64690(11) 1.08740(10) 0.41914(9) 0.01761(18) Uani d . 1 1 . .
H H13A 0.6397 1.0692 0.4957 0.021 Uiso calc R 1 1 . .
C C14 0.59851(12) 1.34179(11) 0.22216(10) 0.02011(19) Uani d . 1 1 . .
C C15 0.79184(12) 0.47723(11) 0.68685(9) 0.01946(19) Uani d . 1 1 . .
C C16 0.67213(13) 0.37082(11) 0.81448(10) 0.0224(2) Uani d . 1 1 . .
H H16A 0.7715 0.3881 0.8834 0.027 Uiso calc R 1 1 . .
H H16B 0.6290 0.2752 0.7573 0.027 Uiso calc R 1 1 . .
C C17 0.56154(14) 0.38291(12) 0.86957(11) 0.0266(2) Uani d . 1 1 . .
H H17A 0.5412 0.3120 0.9164 0.040 Uiso calc R 1 1 . .
H H17B 0.4645 0.3676 0.8006 0.040 Uiso calc R 1 1 . .
H H17C 0.6065 0.4771 0.9277 0.040 Uiso calc R 1 1 . .
C C18 0.94152(11) 0.90747(10) 0.32523(9) 0.01693(17) Uani d . 1 1 . .
H H18A 1.0476 0.9268 0.3839 0.020 Uiso calc R 1 1 . .
H H18B 0.9416 0.9972 0.3083 0.020 Uiso calc R 1 1 . .
C C19 0.89489(11) 0.80215(10) 0.20000(9) 0.01663(17) Uani d . 1 1 . .
H H19A 0.9059 0.7163 0.2182 0.020 Uiso calc R 1 1 . .
H H19B 0.7850 0.7747 0.1453 0.020 Uiso calc R 1 1 . .
C C20 1.15464(11) 0.90256(10) 0.20837(9) 0.01811(18) Uani d . 1 1 . .
H H20A 1.1691 0.8211 0.2350 0.022 Uiso calc R 1 1 . .
H H20B 1.1916 0.9786 0.2861 0.022 Uiso calc R 1 1 . .
C C21 1.24758(12) 0.95334(12) 0.13135(10) 0.0243(2) Uani d . 1 1 . .
H H21A 1.2383 1.0386 0.1099 0.029 Uiso calc R 1 1 . .
H H21B 1.3579 0.9794 0.1835 0.029 Uiso calc R 1 1 . .
C C22 1.03751(13) 0.81211(12) -0.05885(10) 0.0251(2) Uani d . 1 1 . .
H H22A 1.0017 0.7401 -0.1390 0.030 Uiso calc R 1 1 . .
H H22B 1.0260 0.8964 -0.0811 0.030 Uiso calc R 1 1 . .
C C23 0.93906(12) 0.75531(11) 0.01281(9) 0.02070(19) Uani d . 1 1 . .
H H23A 0.8295 0.7302 -0.0411 0.025 Uiso calc R 1 1 . .
H H23B 0.9475 0.6691 0.0324 0.025 Uiso calc R 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'
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
C15 O1 C16 . . 114.83(8) ?
C21 O3 C22 . . 109.12(8) ?
C6 N1 C7 . . 106.10(8) ?
C6 N1 C18 . . 123.21(8) ?
C7 N1 C18 . . 130.41(8) ?
C7 N2 C1 . . 105.02(8) ?
C19 N3 C23 . . 109.01(7) ?
C19 N3 C20 . . 111.75(7) ?
C23 N3 C20 . . 108.99(7) ?
N2 C1 C2 . . 129.84(9) ?
N2 C1 C6 . . 109.97(8) ?
C2 C1 C6 . . 120.18(9) ?
C3 C2 C1 . . 117.21(9) ?
C3 C2 H2A . . 121.4 ?
C1 C2 H2A . . 121.4 ?
C2 C3 C4 . . 121.52(9) ?
C2 C3 C15 . . 122.16(9) ?
C4 C3 C15 . . 116.30(9) ?
C5 C4 C3 . . 122.02(9) ?
C5 C4 H4A . . 119.0 ?
C3 C4 H4A . . 119.0 ?
C4 C5 C6 . . 116.02(9) ?
C4 C5 H5A . . 122.0 ?
C6 C5 H5A . . 122.0 ?
N1 C6 C5 . . 131.06(9) ?
N1 C6 C1 . . 105.89(8) ?
C5 C6 C1 . . 122.99(9) ?
N2 C7 N1 . . 113.01(8) ?
N2 C7 C8 . . 122.72(8) ?
N1 C7 C8 . . 124.07(8) ?
C13 C8 C9 . . 118.97(9) ?
C13 C8 C7 . . 117.53(8) ?
C9 C8 C7 . . 123.49(8) ?
C10 C9 C8 . . 120.37(9) ?
C10 C9 H9A . . 119.8 ?
C8 C9 H9A . . 119.8 ?
C9 C10 C11 . . 119.71(9) ?
C9 C10 H10A . . 120.1 ?
C11 C10 H10A . . 120.1 ?
C12 C11 C10 . . 120.83(9) ?
C12 C11 C14 . . 121.00(9) ?
C10 C11 C14 . . 118.13(9) ?
C11 C12 C13 . . 119.28(9) ?
C11 C12 H12A . . 120.4 ?
C13 C12 H12A . . 120.4 ?
C12 C13 C8 . . 120.76(9) ?
C12 C13 H13A . . 119.6 ?
C8 C13 H13A . . 119.6 ?
F1 C14 F3 . . 107.03(8) ?
F1 C14 F2 . . 106.57(8) ?
F3 C14 F2 . . 106.04(8) ?
F1 C14 C11 . . 112.96(8) ?
F3 C14 C11 . . 112.41(8) ?
F2 C14 C11 . . 111.39(8) ?
O2 C15 O1 . . 123.35(9) ?
O2 C15 C3 . . 123.50(9) ?
O1 C15 C3 . . 113.15(8) ?
O1 C16 C17 . . 107.55(8) ?
O1 C16 H16A . . 110.2 ?
C17 C16 H16A . . 110.2 ?
O1 C16 H16B . . 110.2 ?
C17 C16 H16B . . 110.2 ?
H16A C16 H16B . . 108.5 ?
C16 C17 H17A . . 109.5 ?
C16 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C16 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
N1 C18 C19 . . 111.25(8) ?
N1 C18 H18A . . 109.4 ?
C19 C18 H18A . . 109.4 ?
N1 C18 H18B . . 109.4 ?
C19 C18 H18B . . 109.4 ?
H18A C18 H18B . . 108.0 ?
N3 C19 C18 . . 111.69(7) ?
N3 C19 H19A . . 109.3 ?
C18 C19 H19A . . 109.3 ?
N3 C19 H19B . . 109.3 ?
C18 C19 H19B . . 109.3 ?
H19A C19 H19B . . 107.9 ?
N3 C20 C21 . . 110.18(8) ?
N3 C20 H20A . . 109.6 ?
C21 C20 H20A . . 109.6 ?
N3 C20 H20B . . 109.6 ?
C21 C20 H20B . . 109.6 ?
H20A C20 H20B . . 108.1 ?
O3 C21 C20 . . 111.87(8) ?
O3 C21 H21A . . 109.2 ?
C20 C21 H21A . . 109.2 ?
O3 C21 H21B . . 109.2 ?
C20 C21 H21B . . 109.2 ?
H21A C21 H21B . . 107.9 ?
O3 C22 C23 . . 110.72(8) ?
O3 C22 H22A . . 109.5 ?
C23 C22 H22A . . 109.5 ?
O3 C22 H22B . . 109.5 ?
C23 C22 H22B . . 109.5 ?
H22A C22 H22B . . 108.1 ?
N3 C23 C22 . . 110.37(8) ?
N3 C23 H23A . . 109.6 ?
C22 C23 H23A . . 109.6 ?
N3 C23 H23B . . 109.6 ?
C22 C23 H23B . . 109.6 ?
H23A C23 H23B . . 108.1 ?
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
F1 C14 . 1.3384(12) ?
F2 C14 . 1.3528(12) ?
F3 C14 . 1.3407(12) ?
O1 C15 . 1.3399(12) ?
O1 C16 . 1.4561(12) ?
O2 C15 . 1.2132(13) ?
O3 C21 . 1.4251(13) ?
O3 C22 . 1.4311(13) ?
N1 C6 . 1.3815(12) ?
N1 C7 . 1.3883(12) ?
N1 C18 . 1.4646(12) ?
N2 C7 . 1.3224(12) ?
N2 C1 . 1.3896(12) ?
N3 C19 . 1.4610(12) ?
N3 C23 . 1.4704(12) ?
N3 C20 . 1.4722(12) ?
C1 C2 . 1.4000(13) ?
C1 C6 . 1.4077(13) ?
C2 C3 . 1.3922(13) ?
C2 H2A . 0.9500 ?
C3 C4 . 1.4124(13) ?
C3 C15 . 1.4878(13) ?
C4 C5 . 1.3818(14) ?
C4 H4A . 0.9500 ?
C5 C6 . 1.3977(13) ?
C5 H5A . 0.9500 ?
C7 C8 . 1.4724(13) ?
C8 C13 . 1.4019(13) ?
C8 C9 . 1.4042(13) ?
C9 C10 . 1.3865(14) ?
C9 H9A . 0.9500 ?
C10 C11 . 1.3950(13) ?
C10 H10A . 0.9500 ?
C11 C12 . 1.3895(13) ?
C11 C14 . 1.4975(14) ?
C12 C13 . 1.3915(13) ?
C12 H12A . 0.9500 ?
C13 H13A . 0.9500 ?
C16 C17 . 1.4986(15) ?
C16 H16A . 0.9900 ?
C16 H16B . 0.9900 ?
C17 H17A . 0.9800 ?
C17 H17B . 0.9800 ?
C17 H17C . 0.9800 ?
C18 C19 . 1.5303(13) ?
C18 H18A . 0.9900 ?
C18 H18B . 0.9900 ?
C19 H19A . 0.9900 ?
C19 H19B . 0.9900 ?
C20 C21 . 1.5139(13) ?
C20 H20A . 0.9900 ?
C20 H20B . 0.9900 ?
C21 H21A . 0.9900 ?
C21 H21B . 0.9900 ?
C22 C23 . 1.5152(14) ?
C22 H22A . 0.9900 ?
C22 H22B . 0.9900 ?
C23 H23A . 0.9900 ?
C23 H23B . 0.9900 ?
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
C2 H2A F1 2_676 0.95 2.51 3.4617(15) 175 yes
C10 H10A O3 2_775 0.95 2.38 3.1889(14) 143 yes
C20 H20A O2 2_766 0.99 2.52 3.4878(14) 166 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
C7 N2 C1 C2 . . . . 179.25(10) ?
C7 N2 C1 C6 . . . . 0.28(10) ?
N2 C1 C2 C3 . . . . -177.58(9) ?
C6 C1 C2 C3 . . . . 1.29(14) ?
C1 C2 C3 C4 . . . . 0.72(14) ?
C1 C2 C3 C15 . . . . -177.84(9) ?
C2 C3 C4 C5 . . . . -2.01(15) ?
C15 C3 C4 C5 . . . . 176.62(9) ?
C3 C4 C5 C6 . . . . 1.14(14) ?
C7 N1 C6 C5 . . . . -176.49(10) ?
C18 N1 C6 C5 . . . . -1.98(16) ?
C7 N1 C6 C1 . . . . 0.82(10) ?
C18 N1 C6 C1 . . . . 175.33(8) ?
C4 C5 C6 N1 . . . . 177.86(9) ?
C4 C5 C6 C1 . . . . 0.94(14) ?
N2 C1 C6 N1 . . . . -0.71(10) ?
C2 C1 C6 N1 . . . . -179.79(8) ?
N2 C1 C6 C5 . . . . 176.88(9) ?
C2 C1 C6 C5 . . . . -2.20(14) ?
C1 N2 C7 N1 . . . . 0.27(11) ?
C1 N2 C7 C8 . . . . -174.75(8) ?
C6 N1 C7 N2 . . . . -0.71(11) ?
C18 N1 C7 N2 . . . . -174.67(9) ?
C6 N1 C7 C8 . . . . 174.22(8) ?
C18 N1 C7 C8 . . . . 0.26(15) ?
N2 C7 C8 C13 . . . . 31.52(13) ?
N1 C7 C8 C13 . . . . -142.93(9) ?
N2 C7 C8 C9 . . . . -149.33(10) ?
N1 C7 C8 C9 . . . . 36.21(14) ?
C13 C8 C9 C10 . . . . 3.05(15) ?
C7 C8 C9 C10 . . . . -176.09(9) ?
C8 C9 C10 C11 . . . . -1.29(15) ?
C9 C10 C11 C12 . . . . -1.17(15) ?
C9 C10 C11 C14 . . . . -178.85(9) ?
C10 C11 C12 C13 . . . . 1.81(15) ?
C14 C11 C12 C13 . . . . 179.42(9) ?
C11 C12 C13 C8 . . . . 0.00(15) ?
C9 C8 C13 C12 . . . . -2.40(14) ?
C7 C8 C13 C12 . . . . 176.78(9) ?
C12 C11 C14 F1 . . . . 7.10(13) ?
C10 C11 C14 F1 . . . . -175.22(9) ?
C12 C11 C14 F3 . . . . 128.35(10) ?
C10 C11 C14 F3 . . . . -53.98(12) ?
C12 C11 C14 F2 . . . . -112.80(10) ?
C10 C11 C14 F2 . . . . 64.87(12) ?
C16 O1 C15 O2 . . . . -2.71(14) ?
C16 O1 C15 C3 . . . . 176.96(8) ?
C2 C3 C15 O2 . . . . 169.88(10) ?
C4 C3 C15 O2 . . . . -8.74(15) ?
C2 C3 C15 O1 . . . . -9.78(13) ?
C4 C3 C15 O1 . . . . 171.59(8) ?
C15 O1 C16 C17 . . . . -179.41(9) ?
C6 N1 C18 C19 . . . . 79.90(11) ?
C7 N1 C18 C19 . . . . -107.04(11) ?
C23 N3 C19 C18 . . . . -179.88(8) ?
C20 N3 C19 C18 . . . . 59.59(10) ?
N1 C18 C19 N3 . . . . 173.79(8) ?
C19 N3 C20 C21 . . . . 175.96(8) ?
C23 N3 C20 C21 . . . . 55.41(10) ?
C22 O3 C21 C20 . . . . 59.43(12) ?
N3 C20 C21 O3 . . . . -58.04(12) ?
C21 O3 C22 C23 . . . . -59.79(11) ?
C19 N3 C23 C22 . . . . -178.76(8) ?
C20 N3 C23 C22 . . . . -56.55(11) ?
O3 C22 C23 N3 . . . . 59.56(12) ?
loop_
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1 ChemSpider 30656639
