#------------------------------------------------------------------------------
#$Date: 2019-11-11 17:23:07 +0200 (Mon, 11 Nov 2019) $
#$Revision: 226705 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/52/4035230.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_4035230
loop_
_publ_author_name
'Halli, Juliette'
'Kramer, Philipp'
'Grimmer, Jennifer'
'Bolte, Michael'
'Manolikakes, Georg'
_publ_section_title
;
 Bi(OTf)₃-Catalyzed Diastereoselective One-Pot Synthesis of
 1,3-Diamines with Three Continuous Stereogenic Centers.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12007
_journal_page_last               12022
_journal_paper_doi               10.1021/acs.joc.8b01925
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C29.33 H27.33 Cl F N2 O3'
_chemical_formula_sum            'C29.33 H27.33 Cl F N2 O3'
_chemical_formula_weight         510.31
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   22.0812(19)
_cell_length_b                   22.0812(19)
_cell_length_c                   28.205(3)
_cell_measurement_reflns_used    14234
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      22.73
_cell_measurement_theta_min      3.59
_cell_volume                     11909.7(19)
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  SHELXL
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0996
_diffrn_reflns_av_unetI/netI     0.0653
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            43193
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.859
_diffrn_reflns_theta_min         3.590
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'MULABS (Spek, 2003; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       block
_exptl_crystal_F_000             4812
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         5070
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.1970
_refine_ls_R_factor_gt           0.1088
_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)+(0.1382P)²+9.5865P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2583
_refine_ls_wR_factor_ref         0.3117
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2471
_reflns_number_total             5070
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo8b01925_si_001.cif
_cod_data_source_block           ma100
_cod_original_cell_volume        11910(2)
_cod_database_code               4035230
_shelx_shelxl_version_number     2016/6
_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_min   0.968
_shelx_estimated_absorpt_t_max   0.976
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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 0.4851(2) 0.6416(3) 0.7130(2) 0.158(2) Uani 1 1 d . . . . .
N1 N 0.9701(2) 0.7706(2) 0.69585(16) 0.0640(11) Uani 1 1 d . . . . .
H1 H 1.003(2) 0.801(2) 0.7047(15) 0.040(13) Uiso 1 1 d . . . . .
N2 N 0.8154(2) 0.8083(3) 0.70339(18) 0.0712(13) Uani 1 1 d . . . . .
H2 H 0.802(2) 0.773(2) 0.6976(13) 0.027(11) Uiso 1 1 d . . . . .
O1 O 0.90952(18) 0.65387(17) 0.68879(13) 0.0716(10) Uani 1 1 d . . . . .
O2 O 0.7918(2) 0.8937(2) 0.71815(19) 0.1038(15) Uani 1 1 d . . . . .
C1 C 0.9582(2) 0.7068(3) 0.70698(17) 0.0589(12) Uani 1 1 d . . . . .
C2 C 0.9320(2) 0.7827(2) 0.65869(18) 0.0637(13) Uani 1 1 d . . . . .
H2A H 0.882423 0.743655 0.659619 0.076 Uiso 1 1 calc R U . . .
C3 C 0.9321(3) 0.8520(3) 0.66602(19) 0.0708(14) Uani 1 1 d . . . . .
H3 H 0.981816 0.888976 0.671608 0.085 Uiso 1 1 calc R U . . .
C4 C 0.8904(2) 0.8531(3) 0.70892(19) 0.0670(13) Uani 1 1 d . . . . .
H4 H 0.898318 0.901834 0.710241 0.080 Uiso 1 1 calc R U . . .
C5 C 0.7713(3) 0.8318(3) 0.7108(2) 0.0725(14) Uani 1 1 d . . . . .
C6 C 0.9080(3) 0.8734(3) 0.6212(2) 0.0865(17) Uani 1 1 d . . . . .
H6A H 0.934996 0.872566 0.593868 0.130 Uiso 1 1 calc R U . . .
H6B H 0.858185 0.840644 0.615812 0.130 Uiso 1 1 calc R U . . .
H6C H 0.915418 0.920753 0.625222 0.130 Uiso 1 1 calc R U . . .
C11 C 1.0063(3) 0.7026(3) 0.74219(19) 0.0696(14) Uani 1 1 d . . . . .
C12 C 1.0376(4) 0.7517(4) 0.7792(3) 0.112(2) Uani 1 1 d . . . . .
H12 H 1.027735 0.788700 0.782474 0.135 Uiso 1 1 calc R U . . .
C13 C 1.0827(5) 0.7461(5) 0.8106(4) 0.154(4) Uani 1 1 d . . . . .
H13 H 1.103639 0.779347 0.835390 0.185 Uiso 1 1 calc R U . . .
C14 C 1.0972(5) 0.6936(8) 0.8062(5) 0.173(5) Uani 1 1 d . . . . .
H14 H 1.127783 0.689795 0.828180 0.207 Uiso 1 1 calc R U . . .
C15 C 1.0680(6) 0.6462(7) 0.7704(4) 0.152(4) Uani 1 1 d . . . . .
H15 H 1.080632 0.611162 0.766396 0.183 Uiso 1 1 calc R U . . .
C16 C 1.0198(4) 0.6484(4) 0.7394(2) 0.106(2) Uani 1 1 d . . . . .
H16 H 0.996424 0.612513 0.716543 0.128 Uiso 1 1 calc R U . . .
C21 C 0.9626(4) 0.7807(3) 0.6107(2) 0.0825(17) Uani 1 1 d . . . . .
C22 C 1.0324(4) 0.8234(4) 0.6016(2) 0.105(2) Uani 1 1 d . . . . .
H22 H 1.061183 0.853846 0.625953 0.126 Uiso 1 1 calc R U . . .
C23 C 1.0626(6) 0.8243(6) 0.5591(4) 0.154(4) Uani 1 1 d . . . . .
H23 H 1.111376 0.854419 0.554345 0.185 Uiso 1 1 calc R U . . .
C24 C 1.0217(9) 0.7812(8) 0.5234(4) 0.167(5) Uani 1 1 d . . . . .
H24 H 1.040937 0.780317 0.493491 0.201 Uiso 1 1 calc R U . . .
C25 C 0.9504(7) 0.7387(5) 0.5328(3) 0.129(3) Uani 1 1 d . . . . .
H25 H 0.921313 0.708485 0.508419 0.154 Uiso 1 1 calc R U . . .
C26 C 0.9203(5) 0.7381(4) 0.5751(2) 0.104(2) Uani 1 1 d . . . . .
H26 H 0.871364 0.709116 0.579779 0.125 Uiso 1 1 calc R U . . .
C41 C 0.9114(3) 0.8406(3) 0.7562(2) 0.0816(16) Uani 1 1 d . . . . .
O42 O 0.9761(2) 0.8914(3) 0.77199(18) 0.1177(16) Uani 1 1 d . . . . .
C43 C 0.9857(5) 0.8733(6) 0.8188(3) 0.138(3) Uani 1 1 d . . . . .
C44 C 0.9277(5) 0.8098(6) 0.8299(3) 0.140(3) Uani 1 1 d . . . . .
H44 H 0.919690 0.784263 0.858583 0.168 Uiso 1 1 calc R U . . .
C45 C 0.8807(3) 0.7893(4) 0.7885(3) 0.0991(19) Uani 1 1 d . . . . .
H45 H 0.836866 0.747524 0.785232 0.119 Uiso 1 1 calc R U . . .
C46 C 1.0540(5) 0.9211(7) 0.8399(4) 0.219(7) Uani 1 1 d . . . . .
H46A H 1.090079 0.914520 0.824455 0.328 Uiso 1 1 calc R U . . .
H46B H 1.052880 0.911233 0.873847 0.328 Uiso 1 1 calc R U . . .
H46C H 1.064744 0.969491 0.835422 0.328 Uiso 1 1 calc R U . . .
C51 C 0.6948(3) 0.7791(3) 0.71057(18) 0.0693(13) Uani 1 1 d . . . . .
C52 C 0.6479(3) 0.8019(4) 0.7007(2) 0.0943(18) Uani 1 1 d . . . . .
H52 H 0.664772 0.849862 0.693919 0.113 Uiso 1 1 calc R U . . .
C53 C 0.5777(4) 0.7557(4) 0.7008(3) 0.110(2) Uani 1 1 d . . . . .
H53 H 0.545452 0.770672 0.692974 0.132 Uiso 1 1 calc R U . . .
C54 C 0.5550(3) 0.6883(4) 0.7121(2) 0.097(2) Uani 1 1 d . . . . .
C55 C 0.5984(3) 0.6637(3) 0.7233(2) 0.0898(17) Uani 1 1 d . . . . .
H55 H 0.580181 0.615971 0.731438 0.108 Uiso 1 1 calc R U . . .
C56 C 0.6690(3) 0.7093(3) 0.72274(18) 0.0740(14) Uani 1 1 d . . . . .
H56 H 0.700464 0.693240 0.730637 0.089 Uiso 1 1 calc R U . . .
C1L C 0.333333 0.666667 0.673(12) 0.399(13) Uani 0.5 3 d S TU P . .
H1L H 0.333333 0.666667 0.637569 0.599 Uiso 0.5 3 d R U P . .
Cl1 Cl 0.3374(5) 0.6037(7) 0.7149(5) 0.336(7) Uani 0.5 1 d . . P . .
C2L C 0.000000 1.000000 0.5117(8) 0.121(12) Uani 0.25 3 d DS TU P A 1
H2L H 0.000000 1.000000 0.549644 0.145 Uiso 0.25 3 d R U P A 1
C2L' C 0.000000 1.000000 0.4883(8) 0.121(12) Uani 0.25 3 d DS TU P A 2
H2L' H 0.000000 1.000000 0.450376 0.145 Uiso 0.25 3 d R U P A 2
Cl2 Cl 0.0836(2) 1.0230(4) 0.49422(16) 0.1464(17) Uani 0.5 1 d D . P . .
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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 N1 C2 122.5(5) . .
C1 N1 H1 118(3) . .
C2 N1 H1 118(3) . .
C5 N2 C4 121.7(5) . .
C5 N2 H2 120(3) . .
C4 N2 H2 119(3) . .
O1 C1 N1 121.3(5) . .
O1 C1 C11 121.8(4) . .
N1 C1 C11 116.8(5) . .
N1 C2 C21 109.4(4) . .
N1 C2 C3 111.8(4) . .
C21 C2 C3 111.6(4) . .
N1 C2 H2A 108.0 . .
C21 C2 H2A 108.0 . .
C3 C2 H2A 108.0 . .
C4 C3 C6 110.0(4) . .
C4 C3 C2 114.9(4) . .
C6 C3 C2 111.5(4) . .
C4 C3 H3 106.7 . .
C6 C3 H3 106.7 . .
C2 C3 H3 106.7 . .
N2 C4 C41 109.0(4) . .
N2 C4 C3 113.3(4) . .
C41 C4 C3 117.5(4) . .
N2 C4 H4 105.3 . .
C41 C4 H4 105.3 . .
C3 C4 H4 105.3 . .
O2 C5 N2 121.9(5) . .
O2 C5 C51 120.8(5) . .
N2 C5 C51 117.3(5) . .
C3 C6 H6A 109.5 . .
C3 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C3 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
C16 C11 C12 118.4(6) . .
C16 C11 C1 119.3(6) . .
C12 C11 C1 122.3(5) . .
C13 C12 C11 120.2(8) . .
C13 C12 H12 119.9 . .
C11 C12 H12 119.9 . .
C14 C13 C12 120.5(10) . .
C14 C13 H13 119.8 . .
C12 C13 H13 119.8 . .
C13 C14 C15 120.1(9) . .
C13 C14 H14 119.9 . .
C15 C14 H14 119.9 . .
C14 C15 C16 120.8(10) . .
C14 C15 H15 119.6 . .
C16 C15 H15 119.6 . .
C11 C16 C15 119.8(9) . .
C11 C16 H16 120.1 . .
C15 C16 H16 120.1 . .
C22 C21 C26 118.6(6) . .
C22 C21 C2 120.7(6) . .
C26 C21 C2 120.7(6) . .
C23 C22 C21 123.3(9) . .
C23 C22 H22 118.4 . .
C21 C22 H22 118.4 . .
C24 C23 C22 119.0(11) . .
C24 C23 H23 120.5 . .
C22 C23 H23 120.5 . .
C23 C24 C25 117.3(10) . .
C23 C24 H24 121.3 . .
C25 C24 H24 121.3 . .
C26 C25 C24 123.6(10) . .
C26 C25 H25 118.2 . .
C24 C25 H25 118.2 . .
C25 C26 C21 118.2(9) . .
C25 C26 H26 120.9 . .
C21 C26 H26 120.9 . .
C45 C41 O42 110.4(6) . .
C45 C41 C4 133.9(6) . .
O42 C41 C4 115.7(5) . .
C41 O42 C43 108.1(6) . .
C44 C43 O42 107.6(7) . .
C44 C43 C46 137.4(9) . .
O42 C43 C46 114.7(8) . .
C43 C44 C45 106.5(7) . .
C43 C44 H44 126.7 . .
C45 C44 H44 126.7 . .
C41 C45 C44 107.3(6) . .
C41 C45 H45 126.4 . .
C44 C45 H45 126.4 . .
C43 C46 H46A 109.5 . .
C43 C46 H46B 109.5 . .
H46A C46 H46B 109.5 . .
C43 C46 H46C 109.5 . .
H46A C46 H46C 109.5 . .
H46B C46 H46C 109.5 . .
C52 C51 C56 119.1(5) . .
C52 C51 C5 118.3(5) . .
C56 C51 C5 122.4(5) . .
C53 C52 C51 120.1(6) . .
C53 C52 H52 119.9 . .
C51 C52 H52 119.9 . .
C54 C53 C52 118.8(7) . .
C54 C53 H53 120.6 . .
C52 C53 H53 120.6 . .
C53 C54 C55 123.4(6) . .
C53 C54 F1 119.7(7) . .
C55 C54 F1 116.9(7) . .
C54 C55 C56 118.5(6) . .
C54 C55 H55 120.8 . .
C56 C55 H55 120.8 . .
C55 C56 C51 120.0(5) . .
C55 C56 H56 120.0 . .
C51 C56 H56 120.0 . .
C1L C1L Cl1 129(8) 13_566 3_565
C1L C1L Cl1 129(8) 13_566 2_665
Cl1 C1L Cl1 84(10) 3_565 2_665
C1L C1L Cl1 129(9) 13_566 .
Cl1 C1L Cl1 84(10) 3_565 .
Cl1 C1L Cl1 84(10) 2_665 .
C1L C1L H1L 0.0 13_566 .
Cl1 C1L H1L 129.4 3_565 .
Cl1 C1L H1L 129.4 2_665 .
Cl1 C1L H1L 129.4 . .
C1L Cl1 Cl1 48(6) . 3_565
C1L Cl1 Cl1 48(6) . 2_665
Cl1 Cl1 Cl1 60.002(5) 3_565 2_665
C2L C2L Cl2 84.2(8) 10_576 12_666
C2L C2L Cl2 84.2(9) 10_576 10_576
Cl2 C2L Cl2 119.0(3) 12_666 10_576
C2L C2L Cl2 84.2(8) 10_576 11_456
Cl2 C2L Cl2 119.0(3) 12_666 11_456
Cl2 C2L Cl2 119.0(3) 10_576 11_456
C2L C2L Cl2 73.3(8) 10_576 3_465
Cl2 C2L Cl2 157.5(16) 12_666 3_465
Cl2 C2L Cl2 59.6(2) 10_576 3_465
Cl2 C2L Cl2 59.6(2) 11_456 3_465
C2L C2L Cl2 73.3(8) 10_576 .
Cl2 C2L Cl2 59.6(2) 12_666 .
Cl2 C2L Cl2 157.5(16) 10_576 .
Cl2 C2L Cl2 59.6(2) 11_456 .
Cl2 C2L Cl2 112.1(7) 3_465 .
C2L C2L Cl2 73.3(8) 10_576 2_675
Cl2 C2L Cl2 59.6(2) 12_666 2_675
Cl2 C2L Cl2 59.6(2) 10_576 2_675
Cl2 C2L Cl2 157.5(16) 11_456 2_675
Cl2 C2L Cl2 112.1(7) 3_465 2_675
Cl2 C2L Cl2 112.1(7) . 2_675
C2L C2L H2L 180.0 10_576 .
Cl2 C2L H2L 95.8 12_666 .
Cl2 C2L H2L 95.8 10_576 .
Cl2 C2L H2L 95.8 11_456 .
Cl2 C2L H2L 106.7 3_465 .
Cl2 C2L H2L 106.7 . .
Cl2 C2L H2L 106.7 2_675 .
C2L' C2L' Cl2 84.2(8) 10_576 .
Cl2 C2L' Cl2 119.0(3) 3_465 .
C2L' C2L' Cl2 84.2(8) 10_576 2_675
Cl2 C2L' Cl2 119.0(3) 3_465 2_675
Cl2 C2L' Cl2 119.0(3) . 2_675
Cl2 C2L' Cl2 157.5(16) 3_465 12_666
Cl2 C2L' Cl2 59.6(2) . 12_666
Cl2 C2L' Cl2 59.6(2) 2_675 12_666
Cl2 C2L' Cl2 59.6(2) 3_465 10_576
Cl2 C2L' Cl2 157.5(16) . 10_576
Cl2 C2L' Cl2 59.6(2) 2_675 10_576
Cl2 C2L' Cl2 112.1(7) 12_666 10_576
C2L' C2L' Cl2 73.3(8) 10_576 11_456
Cl2 C2L' Cl2 59.6(2) 3_465 11_456
Cl2 C2L' Cl2 59.6(2) . 11_456
Cl2 C2L' Cl2 157.5(16) 2_675 11_456
Cl2 C2L' Cl2 112.1(7) 12_666 11_456
Cl2 C2L' Cl2 112.1(7) 10_576 11_456
C2L' C2L' H2L' 180.0 10_576 .
Cl2 C2L' H2L' 95.8 3_465 .
Cl2 C2L' H2L' 95.8 . .
Cl2 C2L' H2L' 95.8 2_675 .
Cl2 C2L' H2L' 106.7 12_666 .
Cl2 C2L' H2L' 106.7 10_576 .
Cl2 C2L' H2L' 106.7 11_456 .
C2L Cl2 Cl2 62.1(2) 10_576 11_456
C2L' Cl2 Cl2 62.1(2) . 11_456
C2L Cl2 Cl2 62.1(2) 10_576 12_666
Cl2 Cl2 Cl2 116.3(2) 11_456 12_666
C2L Cl2 C2L' 22.5(12) 10_576 10_576
C2L' Cl2 C2L' 22.5(16) . 10_576
Cl2 Cl2 C2L' 58.30(9) 11_456 10_576
Cl2 Cl2 C2L' 58.30(9) 12_666 10_576
C2L Cl2 C2L 22.5(16) 10_576 .
Cl2 Cl2 C2L 58.30(9) 11_456 .
Cl2 Cl2 C2L 58.30(9) 12_666 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C54 1.362(7) .
N1 C1 1.336(6) .
N1 C2 1.449(6) .
N1 H1 0.74(4) .
N2 C5 1.329(6) .
N2 C4 1.451(7) .
N2 H2 0.69(4) .
O1 C1 1.236(6) .
O2 C5 1.225(6) .
C1 C11 1.491(7) .
C2 C21 1.522(8) .
C2 C3 1.544(6) .
C2 H2A 1.0000 .
C3 C4 1.528(7) .
C3 C6 1.536(7) .
C3 H3 1.0000 .
C4 C41 1.483(8) .
C4 H4 1.0000 .
C5 C51 1.498(7) .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
C11 C16 1.372(8) .
C11 C12 1.411(9) .
C12 C13 1.384(10) .
C12 H12 0.9500 .
C13 C14 1.354(16) .
C13 H13 0.9500 .
C14 C15 1.364(16) .
C14 H14 0.9500 .
C15 C16 1.396(11) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C21 C22 1.370(9) .
C21 C26 1.375(10) .
C22 C23 1.368(11) .
C22 H22 0.9500 .
C23 C24 1.368(15) .
C23 H23 0.9500 .
C24 C25 1.398(15) .
C24 H24 0.9500 .
C25 C26 1.361(10) .
C25 H25 0.9500 .
C26 H26 0.9500 .
C41 C45 1.343(8) .
C41 O42 1.377(7) .
O42 C43 1.425(9) .
C43 C44 1.382(12) .
C43 C46 1.466(12) .
C44 C45 1.476(10) .
C44 H44 0.9500 .
C45 H45 0.9500 .
C46 H46A 0.9800 .
C46 H46B 0.9800 .
C46 H46C 0.9800 .
C51 C52 1.387(8) .
C51 C56 1.393(7) .
C52 C53 1.365(9) .
C52 H52 0.9500 .
C53 C54 1.349(9) .
C53 H53 0.9500 .
C54 C55 1.353(9) .
C55 C56 1.370(8) .
C55 H55 0.9500 .
C56 H56 0.9500 .
C1L C1L 0.4(7) 13_566
C1L Cl1 1.9(2) 3_565
C1L Cl1 1.9(2) 2_665
C1L Cl1 1.9(2) .
C1L H1L 0.9997 .
Cl1 Cl1 2.49(2) 3_565
Cl1 Cl1 2.49(2) 2_665
C2L C2L 0.66(5) 10_576
C2L Cl2 1.659(4) 12_666
C2L Cl2 1.659(4) 10_576
C2L Cl2 1.659(4) 11_456
C2L Cl2 1.723(6) 3_465
C2L Cl2 1.723(6) .
C2L Cl2 1.723(6) 2_675
C2L H2L 1.0690 .
C2L' C2L' 0.66(5) 10_576
C2L' Cl2 1.659(4) 3_465
C2L' Cl2 1.659(4) .
C2L' Cl2 1.659(4) 2_675
C2L' Cl2 1.723(6) 12_666
C2L' Cl2 1.723(6) 10_576
C2L' Cl2 1.723(6) 11_456
C2L' H2L' 1.0684 .
Cl2 Cl2 1.683(5) 11_456
Cl2 Cl2 1.683(5) 12_666
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.74(4) 2.25(4) 2.982(6) 170(4) 2_765
N2 H2 O1 0.69(4) 2.34(4) 2.974(6) 153(4) 13_666
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_4
C2 N1 C1 O1 -6.4(7) . .
C2 N1 C1 C11 173.4(4) . .
C1 N1 C2 C21 -79.6(6) . .
C1 N1 C2 C3 156.3(4) . .
N1 C2 C3 C4 -67.9(5) . .
C21 C2 C3 C4 169.3(5) . .
N1 C2 C3 C6 166.1(4) . .
C21 C2 C3 C6 43.2(6) . .
C5 N2 C4 C41 98.5(6) . .
C5 N2 C4 C3 -128.6(5) . .
C6 C3 C4 N2 57.3(6) . .
C2 C3 C4 N2 -69.5(6) . .
C6 C3 C4 C41 -174.1(5) . .
C2 C3 C4 C41 59.1(6) . .
C4 N2 C5 O2 7.1(9) . .
C4 N2 C5 C51 -171.9(5) . .
O1 C1 C11 C16 30.2(7) . .
N1 C1 C11 C16 -149.7(5) . .
O1 C1 C11 C12 -148.4(5) . .
N1 C1 C11 C12 31.7(7) . .
C16 C11 C12 C13 2.3(10) . .
C1 C11 C12 C13 -179.1(6) . .
C11 C12 C13 C14 0.0(13) . .
C12 C13 C14 C15 0.8(16) . .
C13 C14 C15 C16 -3.8(17) . .
C12 C11 C16 C15 -5.2(10) . .
C1 C11 C16 C15 176.1(6) . .
C14 C15 C16 C11 6.1(14) . .
N1 C2 C21 C22 -55.3(6) . .
C3 C2 C21 C22 69.0(6) . .
N1 C2 C21 C26 127.4(5) . .
C3 C2 C21 C26 -108.3(6) . .
C26 C21 C22 C23 -2.1(10) . .
C2 C21 C22 C23 -179.4(6) . .
C21 C22 C23 C24 0.7(13) . .
C22 C23 C24 C25 0.3(14) . .
C23 C24 C25 C26 0.1(14) . .
C24 C25 C26 C21 -1.4(11) . .
C22 C21 C26 C25 2.3(8) . .
C2 C21 C26 C25 179.7(5) . .
N2 C4 C41 C45 17.0(9) . .
C3 C4 C41 C45 -113.6(7) . .
N2 C4 C41 O42 -163.0(5) . .
C3 C4 C41 O42 66.4(6) . .
C45 C41 O42 C43 -3.8(8) . .
C4 C41 O42 C43 176.2(6) . .
C41 O42 C43 C44 2.9(9) . .
C41 O42 C43 C46 177.5(9) . .
O42 C43 C44 C45 -1.1(10) . .
C46 C43 C44 C45 -173.7(14) . .
O42 C41 C45 C44 3.1(8) . .
C4 C41 C45 C44 -177.0(7) . .
C43 C44 C45 C41 -1.2(9) . .
O2 C5 C51 C52 24.3(8) . .
N2 C5 C51 C52 -156.7(6) . .
O2 C5 C51 C56 -151.6(6) . .
N2 C5 C51 C56 27.4(8) . .
C56 C51 C52 C53 -3.1(9) . .
C5 C51 C52 C53 -179.2(6) . .
C51 C52 C53 C54 2.2(11) . .
C52 C53 C54 C55 -0.2(12) . .
C52 C53 C54 F1 179.1(6) . .
C53 C54 C55 C56 -0.8(10) . .
F1 C54 C55 C56 180.0(6) . .
C54 C55 C56 C51 -0.2(9) . .
C52 C51 C56 C55 2.1(8) . .
C5 C51 C56 C55 178.0(5) . .
C1L C1L Cl1 Cl1 -138(6) 13_566 3_565
Cl1 C1L Cl1 Cl1 85(10) 2_665 3_565
C1L C1L Cl1 Cl1 138(6) 13_566 2_665
Cl1 C1L Cl1 Cl1 -85(10) 3_565 2_665
C2L' C2L' Cl2 Cl2 74.1(5) 10_576 11_456
Cl2 C2L' Cl2 Cl2 -6.0(11) 3_465 11_456
Cl2 C2L' Cl2 Cl2 154.1(18) 2_675 11_456
Cl2 C2L' Cl2 Cl2 148.1(9) 12_666 11_456
Cl2 C2L' Cl2 Cl2 74.1(5) 10_576 11_456
C2L' C2L' Cl2 Cl2 -74.1(5) 10_576 12_666
Cl2 C2L' Cl2 Cl2 -154.1(18) 3_465 12_666
Cl2 C2L' Cl2 Cl2 6.0(11) 2_675 12_666
Cl2 C2L' Cl2 Cl2 -74.1(5) 10_576 12_666
Cl2 C2L' Cl2 Cl2 -148.1(9) 11_456 12_666
Cl2 C2L' Cl2 C2L' -80.0(14) 3_465 10_576
Cl2 C2L' Cl2 C2L' 80.0(14) 2_675 10_576
Cl2 C2L' Cl2 C2L' 74.1(5) 12_666 10_576
Cl2 C2L' Cl2 C2L' 0.000(14) 10_576 10_576
Cl2 C2L' Cl2 C2L' -74.1(5) 11_456 10_576
Cl2 C2L Cl2 C2L -93.0(5) 12_666 10_576
Cl2 C2L Cl2 C2L 0.000(14) 10_576 10_576
Cl2 C2L Cl2 C2L 93.0(6) 11_456 10_576
Cl2 C2L Cl2 C2L 63.6(10) 3_465 10_576
Cl2 C2L Cl2 C2L -63.6(10) 2_675 10_576
C2L C2L Cl2 Cl2 -93.0(6) 10_576 11_456
Cl2 C2L Cl2 Cl2 173.9(11) 12_666 11_456
Cl2 C2L Cl2 Cl2 -93.0(6) 10_576 11_456
Cl2 C2L Cl2 Cl2 -29.5(7) 3_465 11_456
Cl2 C2L Cl2 Cl2 -156.6(15) 2_675 11_456
C2L C2L Cl2 Cl2 93.0(6) 10_576 12_666
Cl2 C2L Cl2 Cl2 93.0(6) 10_576 12_666
Cl2 C2L Cl2 Cl2 -173.9(11) 11_456 12_666
Cl2 C2L Cl2 Cl2 156.6(15) 3_465 12_666
Cl2 C2L Cl2 Cl2 29.5(7) 2_675 12_666
