#------------------------------------------------------------------------------
#$Date: 2021-01-01 02:30:21 +0200 (Fri, 01 Jan 2021) $
#$Revision: 260328 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/54/4135487.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_4135487
loop_
_publ_author_name
'Yao, Ya-Hong'
'Yang, Hui-Yi'
'Chen, Ming'
'Wu, Fei'
'Xu, Xing-Xing'
'Guan, Zheng-Hui'
_publ_section_title
;
 Asymmetric Markovnikov Hydroaminocarbonylation of Alkenes Enabled by
 Palladium-Monodentate Phosphoramidite Catalysis
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c11249
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H14 Cl N O'
_chemical_formula_sum            'C15 H14 Cl N O'
_chemical_formula_weight         259.72
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-09-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   35.208(9)
_cell_length_b                   8.244(2)
_cell_length_c                   9.711(3)
_cell_measurement_reflns_used    2074
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.48
_cell_measurement_theta_min      2.54
_cell_volume                     2818.7(13)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av_unetI/netI     0.0835
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15366
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.322
_diffrn_reflns_theta_min         2.175
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6194
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1113 before and 0.0610 after correction. The Ratio of minimum to maximum transmission is 0.8310. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 1028 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         5684
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.969
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0537
_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)+(0.0433P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1067
_refine_ls_wR_factor_ref         0.1243
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                3468
_reflns_number_total             5684
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c11249_si_002.cif
_cod_data_source_block           xb2433
_cod_database_code               4135487
_shelx_shelxl_version_number     2018/3
_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   0.975
_shelx_estimated_absorpt_t_min   0.965
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C21(H21)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C14(H14), C15(H15), N2(H2A), C17(H17), C18(H18), C23(H23), C24(H24), C25(H25),
 C26(H26), C27(H27), C29(H29), C30(H30)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C28(H28A,H28B,H28C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -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_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
Cl1 Cl 1.05057(3) 1.33967(17) 0.15680(14) 0.0718(4) Uani 1 1 d . . . . .
O1 O 0.87703(8) 1.0260(4) -0.0422(3) 0.0623(8) Uani 1 1 d . . . . .
N1 N 0.89720(9) 1.0476(4) 0.1785(3) 0.0482(8) Uani 1 1 d . . . . .
H1 H 0.889903 1.030938 0.261873 0.058 Uiso 1 1 calc R . . . .
C1 C 1.00518(10) 1.2551(5) 0.1598(4) 0.0506(10) Uani 1 1 d . . . . .
C2 C 0.98674(11) 1.2202(6) 0.0403(5) 0.0609(13) Uani 1 1 d . . . . .
H2 H 0.998559 1.241403 -0.043471 0.073 Uiso 1 1 calc R . . . .
C3 C 0.95092(12) 1.1541(6) 0.0415(4) 0.0564(11) Uani 1 1 d . . . . .
H3 H 0.938400 1.133185 -0.040887 0.068 Uiso 1 1 calc R . . . .
C4 C 0.93352(10) 1.1188(4) 0.1657(5) 0.0436(9) Uani 1 1 d . . . . .
C5 C 0.87219(11) 1.0018(5) 0.0813(4) 0.0493(11) Uani 1 1 d . . . . .
C6 C 0.83684(11) 0.9157(5) 0.1359(5) 0.0566(12) Uani 1 1 d . . . . .
H6 H 0.839284 0.908075 0.236233 0.068 Uiso 1 1 calc R . . . .
C7 C 0.83692(11) 0.7449(6) 0.0789(5) 0.0533(11) Uani 1 1 d . . . . .
C8 C 0.85402(12) 0.6215(6) 0.1521(6) 0.0712(14) Uani 1 1 d . . . . .
H8 H 0.864227 0.643086 0.238459 0.085 Uiso 1 1 calc R . . . .
C9 C 0.85626(16) 0.4653(8) 0.0987(9) 0.096(2) Uani 1 1 d . . . . .
H9 H 0.868166 0.383127 0.148093 0.115 Uiso 1 1 calc R . . . .
C10 C 0.84087(19) 0.4348(8) -0.0259(10) 0.109(2) Uani 1 1 d . . . . .
H10 H 0.842385 0.330459 -0.061998 0.130 Uiso 1 1 calc R . . . .
C11 C 0.82309(18) 0.5534(8) -0.1007(7) 0.099(2) Uani 1 1 d . . . . .
H11 H 0.812290 0.529565 -0.185732 0.118 Uiso 1 1 calc R . . . .
C12 C 0.82141(14) 0.7095(6) -0.0478(6) 0.0758(15) Uani 1 1 d . . . . .
H12 H 0.809694 0.791137 -0.098453 0.091 Uiso 1 1 calc R . . . .
C13 C 0.80144(13) 1.0141(7) 0.1049(6) 0.0893(18) Uani 1 1 d . . . . .
H13A H 0.802961 1.116883 0.151038 0.134 Uiso 1 1 calc GR . . . .
H13B H 0.779450 0.956281 0.136698 0.134 Uiso 1 1 calc GR . . . .
H13C H 0.799496 1.031349 0.007405 0.134 Uiso 1 1 calc GR . . . .
C14 C 0.95244(12) 1.1544(6) 0.2862(4) 0.0588(12) Uani 1 1 d . . . . .
H14 H 0.940874 1.132824 0.370318 0.071 Uiso 1 1 calc R . . . .
C15 C 0.98852(12) 1.2220(6) 0.2837(5) 0.0638(14) Uani 1 1 d . . . . .
H15 H 1.001214 1.244634 0.365416 0.077 Uiso 1 1 calc R . . . .
Cl2 Cl 0.96787(4) 0.24889(18) 0.66502(14) 0.0852(4) Uani 1 1 d . . . . .
O2 O 0.88304(8) 0.9494(5) 0.4564(3) 0.0747(10) Uani 1 1 d . . . . .
N2 N 0.89049(9) 0.8864(5) 0.6800(4) 0.0565(9) Uani 1 1 d . . . . .
H2A H 0.886423 0.921718 0.762045 0.068 Uiso 1 1 calc R . . . .
C16 C 0.94690(12) 0.4420(6) 0.6684(5) 0.0601(11) Uani 1 1 d . . . . .
C17 C 0.94153(12) 0.5247(7) 0.5479(5) 0.0685(13) Uani 1 1 d . . . . .
H17 H 0.950045 0.480528 0.465331 0.082 Uiso 1 1 calc R . . . .
C18 C 0.92361(12) 0.6727(7) 0.5484(5) 0.0639(13) Uani 1 1 d . . . . .
H18 H 0.919897 0.728008 0.466011 0.077 Uiso 1 1 calc R . . . .
C19 C 0.91106(10) 0.7401(6) 0.6707(4) 0.0523(11) Uani 1 1 d . . . . .
C20 C 0.87650(11) 0.9772(6) 0.5780(4) 0.0546(12) Uani 1 1 d . . . . .
C21 C 0.84990(11) 1.1123(6) 0.6221(5) 0.0578(12) Uani 1 1 d . . . . .
H21 H 0.858501 1.151910 0.712019 0.069 Uiso 1 1 calc R . . . .
C22 C 0.80969(11) 1.0481(6) 0.6393(5) 0.0547(11) Uani 1 1 d . . . . .
C23 C 0.78507(13) 1.1188(7) 0.7280(6) 0.0736(15) Uani 1 1 d . . . . .
H23 H 0.793396 1.207240 0.779170 0.088 Uiso 1 1 calc R . . . .
C24 C 0.74822(15) 1.0660(9) 0.7461(7) 0.0958(19) Uani 1 1 d . . . . .
H24 H 0.732052 1.118192 0.807531 0.115 Uiso 1 1 calc R . . . .
C25 C 0.73623(16) 0.9375(10) 0.6730(8) 0.106(2) Uani 1 1 d . . . . .
H25 H 0.711397 0.900989 0.683460 0.127 Uiso 1 1 calc R . . . .
C26 C 0.75958(17) 0.8609(10) 0.5850(7) 0.127(3) Uani 1 1 d . . . . .
H26 H 0.751136 0.770514 0.536535 0.152 Uiso 1 1 calc R . . . .
C27 C 0.79651(14) 0.9175(8) 0.5669(6) 0.096(2) Uani 1 1 d . . . . .
H27 H 0.812464 0.865707 0.504490 0.116 Uiso 1 1 calc R . . . .
C28 C 0.85121(14) 1.2544(7) 0.5214(7) 0.0906(18) Uani 1 1 d . . . . .
H28A H 0.877058 1.288529 0.508985 0.136 Uiso 1 1 calc GR . . . .
H28B H 0.836537 1.342938 0.557404 0.136 Uiso 1 1 calc GR . . . .
H28C H 0.840855 1.221210 0.434374 0.136 Uiso 1 1 calc GR . . . .
C29 C 0.91769(13) 0.6576(7) 0.7922(4) 0.0704(14) Uani 1 1 d . . . . .
H29 H 0.909887 0.702648 0.875311 0.084 Uiso 1 1 calc R . . . .
C30 C 0.93580(13) 0.5088(7) 0.7915(5) 0.0743(15) Uani 1 1 d . . . . .
H30 H 0.940423 0.454410 0.873692 0.089 Uiso 1 1 calc R . . . .
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'
Cl Cl 0.1484 0.1585 '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'
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
C4 N1 H1 114.8 . . ?
C5 N1 H1 114.8 . . ?
C5 N1 C4 130.3(4) . . ?
C2 C1 Cl1 120.5(3) . . ?
C2 C1 C15 120.3(4) . . ?
C15 C1 Cl1 119.2(3) . . ?
C1 C2 H2 119.5 . . ?
C1 C2 C3 120.9(4) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.9(4) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 N1 124.4(4) . . ?
C14 C4 N1 116.8(4) . . ?
C14 C4 C3 118.8(4) . . ?
O1 C5 N1 123.3(4) . . ?
O1 C5 C6 121.9(4) . . ?
N1 C5 C6 114.8(4) . . ?
C5 C6 H6 107.7 . . ?
C7 C6 C5 107.7(3) . . ?
C7 C6 H6 107.7 . . ?
C7 C6 C13 115.2(4) . . ?
C13 C6 C5 110.6(4) . . ?
C13 C6 H6 107.7 . . ?
C8 C7 C6 120.0(4) . . ?
C12 C7 C6 121.5(4) . . ?
C12 C7 C8 118.5(5) . . ?
C7 C8 H8 119.5 . . ?
C7 C8 C9 121.1(6) . . ?
C9 C8 H8 119.5 . . ?
C8 C9 H9 120.5 . . ?
C10 C9 C8 119.0(7) . . ?
C10 C9 H9 120.5 . . ?
C9 C10 H10 119.1 . . ?
C9 C10 C11 121.7(7) . . ?
C11 C10 H10 119.1 . . ?
C10 C11 H11 120.5 . . ?
C10 C11 C12 119.1(6) . . ?
C12 C11 H11 120.5 . . ?
C7 C12 C11 120.7(6) . . ?
C7 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C6 C13 H13A 109.5 . . ?
C6 C13 H13B 109.5 . . ?
C6 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C4 C14 H14 119.6 . . ?
C4 C14 C15 120.9(4) . . ?
C15 C14 H14 119.6 . . ?
C1 C15 C14 119.3(4) . . ?
C1 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C19 N2 H2A 115.8 . . ?
C20 N2 H2A 115.8 . . ?
C20 N2 C19 128.4(4) . . ?
C17 C16 Cl2 119.6(4) . . ?
C17 C16 C30 120.4(5) . . ?
C30 C16 Cl2 120.0(4) . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.2(5) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.4(5) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 N2 124.3(4) . . ?
C29 C19 N2 116.9(4) . . ?
C29 C19 C18 118.8(4) . . ?
O2 C20 N2 122.8(5) . . ?
O2 C20 C21 121.7(4) . . ?
N2 C20 C21 115.4(4) . . ?
C20 C21 H21 107.8 . . ?
C20 C21 C22 110.5(4) . . ?
C20 C21 C28 111.3(4) . . ?
C22 C21 H21 107.8 . . ?
C22 C21 C28 111.4(4) . . ?
C28 C21 H21 107.8 . . ?
C23 C22 C21 121.1(4) . . ?
C23 C22 C27 116.7(4) . . ?
C27 C22 C21 122.2(4) . . ?
C22 C23 H23 118.4 . . ?
C22 C23 C24 123.2(5) . . ?
C24 C23 H23 118.4 . . ?
C23 C24 H24 120.8 . . ?
C25 C24 C23 118.5(6) . . ?
C25 C24 H24 120.8 . . ?
C24 C25 H25 119.5 . . ?
C26 C25 C24 121.0(6) . . ?
C26 C25 H25 119.5 . . ?
C25 C26 H26 120.2 . . ?
C25 C26 C27 119.6(6) . . ?
C27 C26 H26 120.2 . . ?
C22 C27 C26 121.0(5) . . ?
C22 C27 H27 119.5 . . ?
C26 C27 H27 119.5 . . ?
C21 C28 H28A 109.5 . . ?
C21 C28 H28B 109.5 . . ?
C21 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C19 C29 H29 119.7 . . ?
C19 C29 C30 120.7(4) . . ?
C30 C29 H29 119.7 . . ?
C16 C30 C29 119.4(5) . . ?
C16 C30 H30 120.3 . . ?
C29 C30 H30 120.3 . . ?
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
Cl1 C1 1.744(4) . ?
O1 C5 1.228(5) . ?
N1 H1 0.8600 . ?
N1 C4 1.413(5) . ?
N1 C5 1.345(5) . ?
C1 C2 1.361(6) . ?
C1 C15 1.366(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.374(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.383(6) . ?
C4 C14 1.378(6) . ?
C5 C6 1.527(6) . ?
C6 H6 0.9800 . ?
C6 C7 1.513(6) . ?
C6 C13 1.517(6) . ?
C7 C8 1.379(6) . ?
C7 C12 1.378(7) . ?
C8 H8 0.9300 . ?
C8 C9 1.390(8) . ?
C9 H9 0.9300 . ?
C9 C10 1.350(9) . ?
C10 H10 0.9300 . ?
C10 C11 1.369(9) . ?
C11 H11 0.9300 . ?
C11 C12 1.387(8) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14 0.9300 . ?
C14 C15 1.387(6) . ?
C15 H15 0.9300 . ?
Cl2 C16 1.755(5) . ?
O2 C20 1.225(5) . ?
N2 H2A 0.8600 . ?
N2 C19 1.410(6) . ?
N2 C20 1.336(5) . ?
C16 C17 1.368(6) . ?
C16 C30 1.373(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.374(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.383(6) . ?
C19 C29 1.382(6) . ?
C20 C21 1.517(6) . ?
C21 H21 0.9800 . ?
C21 C22 1.521(5) . ?
C21 C28 1.527(7) . ?
C22 C23 1.354(6) . ?
C22 C27 1.367(7) . ?
C23 H23 0.9300 . ?
C23 C24 1.380(7) . ?
C24 H24 0.9300 . ?
C24 C25 1.344(9) . ?
C25 H25 0.9300 . ?
C25 C26 1.343(8) . ?
C26 H26 0.9300 . ?
C26 C27 1.393(7) . ?
C27 H27 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29 0.9300 . ?
C29 C30 1.383(7) . ?
C30 H30 0.9300 . ?
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
Cl1 C1 C2 C3 -179.8(3) . . . . ?
Cl1 C1 C15 C14 -179.8(4) . . . . ?
O1 C5 C6 C7 63.1(6) . . . . ?
O1 C5 C6 C13 -63.7(6) . . . . ?
N1 C4 C14 C15 178.9(4) . . . . ?
N1 C5 C6 C7 -116.8(4) . . . . ?
N1 C5 C6 C13 116.5(4) . . . . ?
C1 C2 C3 C4 -1.5(7) . . . . ?
C2 C1 C15 C14 -0.8(7) . . . . ?
C2 C3 C4 N1 -178.6(4) . . . . ?
C2 C3 C4 C14 1.4(6) . . . . ?
C3 C4 C14 C15 -1.0(6) . . . . ?
C4 N1 C5 O1 -4.7(7) . . . . ?
C4 N1 C5 C6 175.2(4) . . . . ?
C4 C14 C15 C1 0.7(7) . . . . ?
C5 N1 C4 C3 -0.8(6) . . . . ?
C5 N1 C4 C14 179.2(4) . . . . ?
C5 C6 C7 C8 91.0(5) . . . . ?
C5 C6 C7 C12 -86.6(5) . . . . ?
C6 C7 C8 C9 -176.6(4) . . . . ?
C6 C7 C12 C11 177.4(5) . . . . ?
C7 C8 C9 C10 -0.9(8) . . . . ?
C8 C7 C12 C11 -0.2(7) . . . . ?
C8 C9 C10 C11 -0.2(10) . . . . ?
C9 C10 C11 C12 1.1(10) . . . . ?
C10 C11 C12 C7 -0.9(9) . . . . ?
C12 C7 C8 C9 1.1(7) . . . . ?
C13 C6 C7 C8 -145.0(4) . . . . ?
C13 C6 C7 C12 37.4(6) . . . . ?
C15 C1 C2 C3 1.2(7) . . . . ?
Cl2 C16 C17 C18 177.1(3) . . . . ?
Cl2 C16 C30 C29 -177.0(4) . . . . ?
O2 C20 C21 C22 92.3(5) . . . . ?
O2 C20 C21 C28 -32.1(6) . . . . ?
N2 C19 C29 C30 176.4(4) . . . . ?
N2 C20 C21 C22 -84.3(5) . . . . ?
N2 C20 C21 C28 151.3(4) . . . . ?
C16 C17 C18 C19 0.4(7) . . . . ?
C17 C16 C30 C29 2.7(7) . . . . ?
C17 C18 C19 N2 -176.1(4) . . . . ?
C17 C18 C19 C29 1.5(7) . . . . ?
C18 C19 C29 C30 -1.4(7) . . . . ?
C19 N2 C20 O2 -6.7(7) . . . . ?
C19 N2 C20 C21 169.9(4) . . . . ?
C19 C29 C30 C16 -0.7(8) . . . . ?
C20 N2 C19 C18 6.7(7) . . . . ?
C20 N2 C19 C29 -171.0(4) . . . . ?
C20 C21 C22 C23 152.3(5) . . . . ?
C20 C21 C22 C27 -27.8(6) . . . . ?
C21 C22 C23 C24 179.3(5) . . . . ?
C21 C22 C27 C26 179.7(6) . . . . ?
C22 C23 C24 C25 0.5(10) . . . . ?
C23 C22 C27 C26 -0.3(9) . . . . ?
C23 C24 C25 C26 0.6(11) . . . . ?
C24 C25 C26 C27 -1.5(12) . . . . ?
C25 C26 C27 C22 1.3(11) . . . . ?
C27 C22 C23 C24 -0.6(8) . . . . ?
C28 C21 C22 C23 -83.4(6) . . . . ?
C28 C21 C22 C27 96.6(6) . . . . ?
C30 C16 C17 C18 -2.6(7) . . . . ?
