#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/64/4026406.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_4026406
loop_
_publ_author_name
'Hidetsugu Tabata'
'Naoya Wada'
'Yuko Takada'
'Tetsuta Oshitari'
'Hideyo Takahashi'
'Hideaki Natsugari'
_publ_section_title
;
 Isolation and Characterization of Atropisomers of Seven-Membered-Ring
 Benzolactams
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5123
_journal_page_last               5131
_journal_paper_doi               10.1021/jo2008725
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C20 H22 Cl N3 O2 '
_chemical_formula_sum            'C20 H22 Cl N3 O2'
_chemical_formula_weight         371.87
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   8.18197(15)
_cell_length_b                   8.69418(16)
_cell_length_c                   26.3682(5)
_cell_measurement_reflns_used    16124
_cell_measurement_temperature    173.1
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      3.4
_cell_volume                     1875.72(6)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SIR92
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.040
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            19136
_diffrn_reflns_theta_full        68.24
_diffrn_reflns_theta_max         68.24
_exptl_absorpt_coefficient_mu    1.958
_exptl_absorpt_correction_T_max  0.822
_exptl_absorpt_correction_T_min  0.694
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_description       block
_exptl_crystal_F_000             784.00
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.38
_refine_diff_density_min         -0.34
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1422 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.003(14)
_refine_ls_extinction_coef       21(4)
_refine_ls_extinction_method
'Larson (1970) Crystallographic Computing eq. 22'
_refine_ls_goodness_of_fit_ref   0.737
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     325
_refine_ls_number_reflns         3410
_refine_ls_R_factor_gt           0.0286
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 1/[1.0000σ(Fo²)]/(4Fo²)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0660
_reflns_number_gt                2625
_reflns_number_total             3410
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            jo2008725_si_004.cif
_cod_data_source_block           '_081020'
_cod_original_cell_volume        1875.71(6)
_cod_original_formula_sum        'C20 H22 Cl N3 O2 '
_cod_database_code               4026406
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2+X,1/2-Y,-Z
3 -X,1/2+Y,1/2-Z
4 1/2-X,-Y,1/2+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_symmetry_multiplicity
_atom_site_calc_flag
Cl(1) Cl 0.64451(8) 0.71710(9) 0.72050(2) 0.05777(19) Uani 1.00 1 d
O(1) O 0.45166(17) 0.52444(19) 0.88058(6) 0.0455(4) Uani 1.00 1 d
O(2) O 0.61028(19) 1.01739(17) 0.88763(6) 0.0469(4) Uani 1.00 1 d
N(1) N 0.6468(2) 0.63628(19) 0.83161(6) 0.0308(4) Uani 1.00 1 d
N(2) N 0.9143(2) 0.51321(19) 0.88233(6) 0.0312(4) Uani 1.00 1 d
N(3) N 0.7386(2) 0.8060(2) 0.91773(7) 0.0314(5) Uani 1.00 1 d
C(1) C 0.7997(2) 0.6224(2) 0.80597(8) 0.0302(5) Uani 1.00 1 d
C(2) C 0.8165(2) 0.6645(2) 0.75554(9) 0.0419(6) Uani 1.00 1 d
C(3) C 0.9662(3) 0.6633(3) 0.73130(10) 0.0548(8) Uani 1.00 1 d
C(4) C 1.1015(3) 0.6164(3) 0.75768(10) 0.0532(8) Uani 1.00 1 d
C(5) C 1.0892(2) 0.5663(2) 0.80769(9) 0.0419(7) Uani 1.00 1 d
C(6) C 0.9380(2) 0.5661(2) 0.83173(8) 0.0316(5) Uani 1.00 1 d
C(7) C 0.8202(2) 0.3688(2) 0.88612(8) 0.0347(6) Uani 1.00 1 d
C(8) C 0.6719(2) 0.3648(2) 0.85101(9) 0.0351(6) Uani 1.00 1 d
C(9) C 0.5778(2) 0.5122(2) 0.85588(8) 0.0342(5) Uani 1.00 1 d
C(10) C 1.0642(3) 0.5014(3) 0.91282(10) 0.0438(7) Uani 1.00 1 d
C(11) C 0.5779(2) 0.7892(2) 0.83967(9) 0.0364(6) Uani 1.00 1 d
C(12) C 0.6458(2) 0.8810(2) 0.88409(8) 0.0333(5) Uani 1.00 1 d
C(13) C 0.8080(2) 0.8826(2) 0.96196(8) 0.0325(5) Uani 1.00 1 d
C(14) C 0.9631(2) 0.9729(2) 0.94967(7) 0.0298(5) Uani 1.00 1 d
C(15) C 1.0224(2) 1.0768(2) 0.98523(8) 0.0337(6) Uani 1.00 1 d
C(16) C 1.1683(3) 1.1547(2) 0.97679(9) 0.0395(6) Uani 1.00 1 d
C(17) C 1.2570(2) 1.1277(2) 0.93328(10) 0.0416(6) Uani 1.00 1 d
C(18) C 1.1984(2) 1.0258(2) 0.89771(9) 0.0390(6) Uani 1.00 1 d
C(19) C 1.0507(2) 0.9493(2) 0.90555(8) 0.0347(6) Uani 1.00 1 d
C(20) C 0.8395(3) 0.7645(3) 1.00341(9) 0.0395(7) Uani 1.00 1 d
H(1) H 0.967(3) 0.692(2) 0.6964(8) 0.059(7) Uiso 1.00 1 c
H(2) H 1.206(2) 0.614(2) 0.7430(8) 0.052(7) Uiso 1.00 1 c
H(3) H 1.188(2) 0.532(2) 0.8250(7) 0.036(5) Uiso 1.00 1 c
H(4) H 0.781(2) 0.357(2) 0.9220(8) 0.037(5) Uiso 1.00 1 c
H(5) H 0.889(2) 0.279(2) 0.8786(7) 0.041(6) Uiso 1.00 1 c
H(6) H 0.602(2) 0.280(2) 0.8620(7) 0.038(5) Uiso 1.00 1 c
H(7) H 0.708(2) 0.353(2) 0.8156(7) 0.027(5) Uiso 1.00 1 c
H(8) H 1.141(2) 0.417(2) 0.9000(7) 0.046(6) Uiso 1.00 1 c
H(9) H 1.025(2) 0.472(2) 0.9498(8) 0.046(6) Uiso 1.00 1 c
H(10) H 1.119(2) 0.602(2) 0.9149(7) 0.044(6) Uiso 1.00 1 c
H(11) H 0.460(2) 0.777(2) 0.8448(7) 0.041(6) Uiso 1.00 1 c
H(12) H 0.595(2) 0.855(2) 0.8105(7) 0.021(5) Uiso 1.00 1 c
H(13) H 0.772(2) 0.712(2) 0.9106(8) 0.039(6) Uiso 1.00 1 c
H(14) H 0.723(2) 0.955(2) 0.9720(7) 0.028(5) Uiso 1.00 1 c
H(15) H 0.969(2) 1.093(2) 1.0160(7) 0.038(6) Uiso 1.00 1 c
H(16) H 1.201(2) 1.227(2) 1.0033(8) 0.040(6) Uiso 1.00 1 c
H(17) H 1.361(2) 1.183(2) 0.9278(7) 0.052(6) Uiso 1.00 1 c
H(18) H 1.254(2) 1.008(2) 0.8667(8) 0.047(6) Uiso 1.00 1 c
H(19) H 1.009(2) 0.878(2) 0.8802(7) 0.029(5) Uiso 1.00 1 c
H(20) H 0.928(3) 0.694(2) 0.9918(8) 0.057(7) Uiso 1.00 1 c
H(21) H 0.744(2) 0.705(2) 1.0107(8) 0.042(6) Uiso 1.00 1 c
H(22) H 0.876(2) 0.812(2) 1.0326(7) 0.030(5) Uiso 1.00 1 c
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.018 0.009
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O 0.049 0.032
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.031 0.018
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.364 0.702
;
International Tables for Crystallography
(1992, 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_publ_flag
C(1) N(1) C(9) 120.92(16) yes
C(1) N(1) C(11) 118.99(16) yes
C(9) N(1) C(11) 119.22(17) yes
C(6) N(2) C(7) 114.12(15) yes
C(6) N(2) C(10) 114.93(17) yes
C(7) N(2) C(10) 109.79(17) yes
C(12) N(3) C(13) 121.96(18) yes
N(1) C(1) C(2) 121.27(19) yes
N(1) C(1) C(6) 120.36(18) yes
C(2) C(1) C(6) 118.36(19) yes
Cl(1) C(2) C(1) 119.81(17) yes
Cl(1) C(2) C(3) 118.18(18) yes
C(1) C(2) C(3) 122.0(2) yes
C(2) C(3) C(4) 118.9(2) yes
C(3) C(4) C(5) 121.1(2) yes
C(4) C(5) C(6) 119.8(2) yes
N(2) C(6) C(1) 117.07(17) yes
N(2) C(6) C(5) 123.27(18) yes
C(1) C(6) C(5) 119.66(19) yes
N(2) C(7) C(8) 113.16(17) yes
C(7) C(8) C(9) 109.62(18) yes
O(1) C(9) N(1) 121.7(2) yes
O(1) C(9) C(8) 123.5(2) yes
N(1) C(9) C(8) 114.83(17) yes
N(1) C(11) C(12) 116.63(18) yes
O(2) C(12) N(3) 123.8(2) yes
O(2) C(12) C(11) 118.65(19) yes
N(3) C(12) C(11) 117.54(19) yes
N(3) C(13) C(14) 112.87(16) yes
N(3) C(13) C(20) 109.43(18) yes
C(14) C(13) C(20) 111.01(18) yes
C(13) C(14) C(15) 118.77(17) yes
C(13) C(14) C(19) 122.23(18) yes
C(15) C(14) C(19) 118.93(19) yes
C(14) C(15) C(16) 120.6(2) yes
C(15) C(16) C(17) 120.2(2) yes
C(16) C(17) C(18) 119.6(2) yes
C(17) C(18) C(19) 120.5(2) yes
C(14) C(19) C(18) 120.2(2) yes
C(12) N(3) H(13) 119.1(13) no
C(13) N(3) H(13) 118.2(13) no
C(2) C(3) H(1) 117.0(15) no
C(4) C(3) H(1) 124.1(15) no
C(3) C(4) H(2) 122.2(14) no
C(5) C(4) H(2) 116.7(14) no
C(4) C(5) H(3) 118.6(12) no
C(6) C(5) H(3) 121.6(11) no
N(2) C(7) H(4) 108.7(11) no
N(2) C(7) H(5) 111.5(12) no
C(8) C(7) H(4) 108.2(11) no
C(8) C(7) H(5) 108.2(12) no
H(4) C(7) H(5) 106.8(16) no
C(7) C(8) H(6) 107.6(12) no
C(7) C(8) H(7) 110.0(11) no
C(9) C(8) H(6) 108.7(12) no
C(9) C(8) H(7) 108.9(11) no
H(6) C(8) H(7) 112.1(15) no
N(2) C(10) H(8) 112.3(12) no
N(2) C(10) H(9) 105.5(12) no
N(2) C(10) H(10) 110.3(12) no
H(8) C(10) H(9) 108.4(17) no
H(8) C(10) H(10) 112.3(18) no
H(9) C(10) H(10) 107.7(17) no
N(1) C(11) H(11) 107.6(12) no
N(1) C(11) H(12) 111.5(11) no
C(12) C(11) H(11) 108.0(11) no
C(12) C(11) H(12) 104.2(11) no
H(11) C(11) H(12) 108.6(16) no
N(3) C(13) H(14) 103.7(11) no
C(14) C(13) H(14) 108.3(11) no
C(20) C(13) H(14) 111.3(11) no
C(14) C(15) H(15) 121.2(13) no
C(16) C(15) H(15) 118.1(13) no
C(15) C(16) H(16) 115.9(12) no
C(17) C(16) H(16) 123.9(12) no
C(16) C(17) H(17) 119.6(12) no
C(18) C(17) H(17) 120.9(12) no
C(17) C(18) H(18) 122.0(14) no
C(19) C(18) H(18) 117.4(13) no
C(14) C(19) H(19) 119.6(11) no
C(18) C(19) H(19) 120.2(11) no
C(13) C(20) H(20) 108.4(13) no
C(13) C(20) H(21) 111.8(13) no
C(13) C(20) H(22) 110.7(12) no
H(20) C(20) H(21) 109(2) no
H(20) C(20) H(22) 107.1(18) no
H(21) C(20) H(22) 109.8(18) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl(1) C(2) 1.745(2) yes
O(1) C(9) 1.225(2) yes
O(2) C(12) 1.225(2) yes
N(1) C(1) 1.427(2) yes
N(1) C(9) 1.375(2) yes
N(1) C(11) 1.460(2) yes
N(2) C(6) 1.424(2) yes
N(2) C(7) 1.476(2) yes
N(2) C(10) 1.470(2) yes
N(3) C(12) 1.337(2) yes
N(3) C(13) 1.458(2) yes
C(1) C(2) 1.386(3) yes
C(1) C(6) 1.408(2) yes
C(2) C(3) 1.382(3) yes
C(3) C(4) 1.369(3) yes
C(4) C(5) 1.392(3) yes
C(5) C(6) 1.390(3) yes
C(7) C(8) 1.527(3) yes
C(8) C(9) 1.501(3) yes
C(11) C(12) 1.522(3) yes
C(13) C(14) 1.527(2) yes
C(13) C(20) 1.521(3) yes
C(14) C(15) 1.389(2) yes
C(14) C(19) 1.382(2) yes
C(15) C(16) 1.390(3) yes
C(16) C(17) 1.378(3) yes
C(17) C(18) 1.376(3) yes
C(18) C(19) 1.395(3) yes
N(3) H(13) 0.88(2) no
C(3) H(1) 0.95(2) no
C(4) H(2) 0.94(2) no
C(5) H(3) 0.97(2) no
C(7) H(4) 1.00(2) no
C(7) H(5) 0.98(2) no
C(8) H(6) 0.98(2) no
C(8) H(7) 0.984(19) no
C(10) H(8) 1.02(2) no
C(10) H(9) 1.06(2) no
C(10) H(10) 0.98(2) no
C(11) H(11) 0.98(2) no
C(11) H(12) 0.970(18) no
C(13) H(14) 0.975(19) no
C(15) H(15) 0.93(2) no
C(16) H(16) 0.98(2) no
C(17) H(17) 0.99(2) no
C(18) H(18) 0.95(2) no
C(19) H(19) 0.971(19) no
C(20) H(20) 1.00(2) no
C(20) H(21) 0.95(2) no
C(20) H(22) 0.923(19) no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
Cl(1) C(8) 3.450(2) 3_656
O(1) C(5) 3.553(2) 1_455
O(1) C(10) 3.288(2) 1_455
O(2) C(7) 3.506(2) 1_565
O(2) C(8) 3.211(2) 1_565
O(2) C(17) 3.275(2) 1_455
O(2) C(18) 3.381(2) 1_455
C(5) O(1) 3.553(2) 1_655
C(7) O(2) 3.506(2) 1_545
C(8) Cl(1) 3.450(2) 3_646
C(8) O(2) 3.211(2) 1_545
C(10) O(1) 3.288(2) 1_655
C(10) C(16) 3.558(3) 1_545
C(16) C(10) 3.558(3) 1_565
C(17) O(2) 3.275(2) 1_655
C(18) O(2) 3.381(2) 1_655
Cl(1) H(3) 3.29(2) 3_756
Cl(1) H(6) 3.02(2) 3_656
Cl(1) H(7) 3.256(19) 3_656
Cl(1) H(18) 3.05(2) 3_746
O(1) H(3) 2.61(2) 1_455
O(1) H(8) 2.76(2) 1_455
O(1) H(10) 2.95(2) 1_455
O(1) H(15) 2.915(19) 2_467
O(1) H(17) 3.30(2) 1_445
O(1) H(22) 2.766(19) 2_467
O(2) H(4) 3.39(2) 1_565
O(2) H(5) 3.23(2) 1_565
O(2) H(6) 2.38(2) 1_565
O(2) H(7) 3.570(18) 1_565
O(2) H(17) 2.71(2) 1_455
O(2) H(18) 2.97(2) 1_455
N(3) H(20) 3.49(2) 2_467
N(3) H(22) 3.40(2) 2_467
C(2) H(18) 3.55(2) 3_746
C(3) H(5) 3.29(2) 3_756
C(3) H(7) 3.371(19) 3_756
C(3) H(18) 3.43(2) 3_746
C(4) H(7) 3.225(19) 3_756
C(5) H(1) 3.29(2) 3_746
C(6) H(1) 3.42(2) 3_746
C(7) H(1) 3.18(2) 3_746
C(7) H(16) 3.19(2) 2_467
C(8) H(1) 3.54(2) 3_746
C(8) H(2) 3.45(2) 3_746
C(9) H(3) 3.30(2) 1_455
C(10) H(14) 3.326(19) 2_567
C(10) H(16) 3.55(2) 1_545
C(10) H(21) 3.57(2) 2_567
C(10) H(22) 3.35(2) 2_567
C(11) H(18) 3.34(2) 1_455
C(12) H(6) 3.54(2) 1_565
C(12) H(18) 3.42(2) 1_455
C(12) H(22) 3.535(19) 2_467
C(13) H(9) 3.52(2) 2_467
C(13) H(20) 3.41(2) 2_467
C(14) H(5) 3.31(2) 1_565
C(14) H(16) 3.59(2) 2_477
C(14) H(21) 2.96(2) 2_567
C(15) H(4) 3.55(2) 1_565
C(15) H(4) 3.28(2) 2_567
C(15) H(5) 3.49(2) 1_565
C(15) H(9) 3.56(2) 1_565
C(15) H(16) 3.14(2) 2_477
C(15) H(17) 3.37(2) 2_477
C(15) H(21) 3.05(2) 2_567
C(16) H(4) 2.83(2) 2_567
C(16) H(8) 3.06(2) 1_565
C(16) H(9) 3.08(2) 1_565
C(16) H(15) 3.30(2) 2_577
C(16) H(21) 3.21(2) 2_567
C(17) H(5) 3.59(2) 1_565
C(17) H(8) 2.83(2) 1_565
C(17) H(9) 3.57(2) 1_565
C(17) H(15) 3.27(2) 2_577
C(17) H(21) 3.25(2) 2_567
C(18) H(1) 3.18(2) 3_756
C(18) H(5) 3.39(2) 1_565
C(18) H(8) 3.43(2) 1_565
C(18) H(11) 3.35(2) 1_655
C(18) H(21) 3.16(2) 2_567
C(19) H(1) 3.42(2) 3_756
C(19) H(5) 3.23(2) 1_565
C(19) H(21) 3.03(2) 2_567
C(20) H(10) 3.04(2) 2_467
C(20) H(20) 3.39(2) 2_467
C(20) H(21) 3.34(2) 2_567
H(1) C(5) 3.29(2) 3_756
H(1) C(6) 3.42(2) 3_756
H(1) C(7) 3.18(2) 3_756
H(1) C(8) 3.54(2) 3_756
H(1) C(18) 3.18(2) 3_746
H(1) C(19) 3.42(2) 3_746
H(1) H(3) 3.27(3) 3_756
H(1) H(5) 2.42(3) 3_756
H(1) H(7) 3.02(3) 3_756
H(1) H(8) 3.32(3) 3_756
H(1) H(18) 2.93(3) 3_746
H(1) H(19) 3.40(3) 3_746
H(2) C(8) 3.45(2) 3_756
H(2) H(5) 3.59(3) 3_756
H(2) H(6) 3.49(3) 3_756
H(2) H(7) 2.68(2) 3_756
H(2) H(12) 3.11(2) 3_746
H(3) Cl(1) 3.29(2) 3_746
H(3) O(1) 2.61(2) 1_655
H(3) C(9) 3.30(2) 1_655
H(3) H(1) 3.27(3) 3_746
H(3) H(11) 3.13(3) 1_655
H(4) O(2) 3.39(2) 1_545
H(4) C(15) 3.55(2) 1_545
H(4) C(15) 3.28(2) 2_467
H(4) C(16) 2.83(2) 2_467
H(4) H(15) 3.06(2) 2_467
H(4) H(16) 2.20(3) 2_467
H(5) O(2) 3.23(2) 1_545
H(5) C(3) 3.29(2) 3_746
H(5) C(14) 3.31(2) 1_545
H(5) C(15) 3.49(2) 1_545
H(5) C(17) 3.59(2) 1_545
H(5) C(18) 3.39(2) 1_545
H(5) C(19) 3.23(2) 1_545
H(5) H(1) 2.42(3) 3_746
H(5) H(2) 3.59(3) 3_746
H(5) H(16) 3.47(2) 2_467
H(6) Cl(1) 3.02(2) 3_646
H(6) O(2) 2.38(2) 1_545
H(6) C(12) 3.54(2) 1_545
H(6) H(2) 3.49(3) 3_746
H(6) H(15) 3.57(2) 2_467
H(6) H(17) 2.76(3) 1_445
H(7) Cl(1) 3.256(19) 3_646
H(7) O(2) 3.570(18) 1_545
H(7) C(3) 3.371(19) 3_746
H(7) C(4) 3.225(19) 3_746
H(7) H(1) 3.02(3) 3_746
H(7) H(2) 2.68(2) 3_746
H(8) O(1) 2.76(2) 1_655
H(8) C(16) 3.06(2) 1_545
H(8) C(17) 2.83(2) 1_545
H(8) C(18) 3.43(2) 1_545
H(8) H(1) 3.32(3) 3_746
H(8) H(15) 3.48(3) 2_567
H(8) H(16) 3.22(3) 1_545
H(8) H(17) 2.81(3) 1_545
H(8) H(22) 3.53(2) 2_567
H(9) C(13) 3.52(2) 2_567
H(9) C(15) 3.56(2) 1_545
H(9) C(16) 3.08(2) 1_545
H(9) C(17) 3.57(2) 1_545
H(9) H(14) 2.70(2) 2_567
H(9) H(16) 2.93(3) 1_545
H(9) H(16) 3.40(3) 2_467
H(9) H(21) 3.49(3) 2_567
H(9) H(22) 3.47(2) 2_567
H(10) O(1) 2.95(2) 1_655
H(10) C(20) 3.04(2) 2_567
H(10) H(14) 3.14(2) 2_567
H(10) H(21) 2.78(3) 2_567
H(10) H(22) 2.63(2) 2_567
H(11) C(18) 3.35(2) 1_455
H(11) H(3) 3.13(3) 1_455
H(11) H(18) 2.68(3) 1_455
H(11) H(22) 3.39(2) 2_467
H(12) H(2) 3.11(2) 3_756
H(12) H(18) 3.43(2) 1_455
H(13) H(22) 3.57(2) 2_467
H(14) C(10) 3.326(19) 2_467
H(14) H(9) 2.70(2) 2_467
H(14) H(10) 3.14(2) 2_467
H(14) H(16) 2.84(2) 2_477
H(14) H(20) 2.91(3) 2_467
H(15) O(1) 2.91(2) 2_567
H(15) C(16) 3.30(2) 2_477
H(15) C(17) 3.27(2) 2_477
H(15) H(4) 3.06(2) 2_567
H(15) H(6) 3.57(2) 2_567
H(15) H(8) 3.48(3) 2_467
H(15) H(16) 2.73(3) 2_477
H(15) H(17) 2.60(3) 2_477
H(15) H(21) 3.51(3) 2_567
H(16) C(7) 3.19(2) 2_567
H(16) C(10) 3.55(2) 1_565
H(16) C(14) 3.59(2) 2_577
H(16) C(15) 3.14(2) 2_577
H(16) H(4) 2.20(3) 2_567
H(16) H(5) 3.47(2) 2_567
H(16) H(8) 3.22(3) 1_565
H(16) H(9) 2.93(3) 1_565
H(16) H(9) 3.40(3) 2_567
H(16) H(14) 2.84(2) 2_577
H(16) H(15) 2.73(3) 2_577
H(16) H(17) 3.42(3) 2_477
H(17) O(1) 3.30(2) 1_665
H(17) O(2) 2.71(2) 1_655
H(17) C(15) 3.37(2) 2_577
H(17) H(6) 2.76(3) 1_665
H(17) H(8) 2.81(3) 1_565
H(17) H(15) 2.60(2) 2_577
H(17) H(16) 3.42(3) 2_577
H(18) Cl(1) 3.05(2) 3_756
H(18) O(2) 2.97(2) 1_655
H(18) C(2) 3.55(2) 3_756
H(18) C(3) 3.43(2) 3_756
H(18) C(11) 3.34(2) 1_655
H(18) C(12) 3.42(2) 1_655
H(18) H(1) 2.93(3) 3_756
H(18) H(11) 2.68(3) 1_655
H(18) H(12) 3.43(2) 1_655
H(19) H(1) 3.40(3) 3_756
H(19) H(21) 3.54(2) 2_567
H(20) N(3) 3.49(2) 2_567
H(20) C(13) 3.41(2) 2_567
H(20) C(20) 3.39(2) 2_567
H(20) H(14) 2.91(3) 2_567
H(20) H(21) 2.73(3) 2_567
H(21) C(10) 3.57(2) 2_467
H(21) C(14) 2.96(2) 2_467
H(21) C(15) 3.05(2) 2_467
H(21) C(16) 3.21(2) 2_467
H(21) C(17) 3.25(2) 2_467
H(21) C(18) 3.16(2) 2_467
H(21) C(19) 3.03(2) 2_467
H(21) C(20) 3.34(2) 2_467
H(21) H(9) 3.49(3) 2_467
H(21) H(10) 2.78(3) 2_467
H(21) H(15) 3.51(3) 2_467
H(21) H(19) 3.54(2) 2_467
H(21) H(20) 2.73(3) 2_467
H(21) H(22) 3.22(3) 2_467
H(22) O(1) 2.766(19) 2_567
H(22) N(3) 3.40(2) 2_567
H(22) C(10) 3.35(2) 2_467
H(22) C(12) 3.535(19) 2_567
H(22) H(8) 3.53(2) 2_467
H(22) H(9) 3.47(2) 2_467
H(22) H(10) 2.63(2) 2_467
H(22) H(11) 3.39(2) 2_567
H(22) H(13) 3.57(2) 2_567
H(22) H(21) 3.22(3) 2_567
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
C(1) N(1) C(9) O(1) 175.58(18)
C(1) N(1) C(9) C(8) -2.5(2)
C(9) N(1) C(1) C(2) 125.7(2)
C(9) N(1) C(1) C(6) -54.7(2)
C(1) N(1) C(11) C(12) -80.5(2)
C(11) N(1) C(1) C(2) -65.2(2)
C(11) N(1) C(1) C(6) 114.4(2)
C(9) N(1) C(11) C(12) 88.8(2)
C(11) N(1) C(9) O(1) 6.4(2)
C(11) N(1) C(9) C(8) -171.62(18)
C(6) N(2) C(7) C(8) -43.1(2)
C(7) N(2) C(6) C(1) 70.1(2)
C(7) N(2) C(6) C(5) -110.9(2)
C(10) N(2) C(6) C(1) -161.79(19)
C(10) N(2) C(6) C(5) 17.2(2)
C(10) N(2) C(7) C(8) -173.75(18)
C(12) N(3) C(13) C(14) -80.8(2)
C(12) N(3) C(13) C(20) 155.06(19)
C(13) N(3) C(12) O(2) -0.7(3)
C(13) N(3) C(12) C(11) -179.25(18)
N(1) C(1) C(2) Cl(1) -6.6(2)
N(1) C(1) C(2) C(3) 174.8(2)
N(1) C(1) C(6) N(2) 4.9(2)
N(1) C(1) C(6) C(5) -174.18(19)
C(2) C(1) C(6) N(2) -175.53(18)
C(2) C(1) C(6) C(5) 5.4(3)
C(6) C(1) C(2) Cl(1) 173.80(16)
C(6) C(1) C(2) C(3) -4.8(3)
Cl(1) C(2) C(3) C(4) -177.4(2)
C(1) C(2) C(3) C(4) 1.2(3)
C(2) C(3) C(4) C(5) 1.8(4)
C(3) C(4) C(5) C(6) -1.1(3)
C(4) C(5) C(6) N(2) 178.4(2)
C(4) C(5) C(6) C(1) -2.6(3)
N(2) C(7) C(8) C(9) -47.5(2)
C(7) C(8) C(9) O(1) -101.8(2)
C(7) C(8) C(9) N(1) 76.3(2)
N(1) C(11) C(12) O(2) 168.95(18)
N(1) C(11) C(12) N(3) -12.5(2)
N(3) C(13) C(14) C(15) 166.57(18)
N(3) C(13) C(14) C(19) -16.7(2)
C(20) C(13) C(14) C(15) -70.1(2)
C(20) C(13) C(14) C(19) 106.6(2)
C(13) C(14) C(15) C(16) 176.3(2)
C(13) C(14) C(19) C(18) -175.0(2)
C(15) C(14) C(19) C(18) 1.7(3)
C(19) C(14) C(15) C(16) -0.6(3)
C(14) C(15) C(16) C(17) -1.0(3)
C(15) C(16) C(17) C(18) 1.5(3)
C(16) C(17) C(18) C(19) -0.3(3)
C(17) C(18) C(19) C(14) -1.3(3)
