#------------------------------------------------------------------------------
#$Date: 2023-11-10 20:21:08 +0100 (Fri 10 de Nov de 2023) $
#$Revision: 287519 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/73/7117351.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_7117351
loop_
_publ_author_name
'Thomas Simler'
'Andreas A. Danopoulos'
'Pierre Braunstein'
_publ_section_title
;
 N-Heterocyclic carbene-phosphino-picolines as precursors of anionic
 'pincer' ligands with dearomatised pyridine backbones; transmetallation
 from potassium to chromium
;
_journal_name_full               Chem.Commun.
_journal_page_first              10699
_journal_paper_doi               10.1039/C5cc02920A
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C33 H48 N3 P, C H2 Cl2, 2(Br)'
_chemical_formula_sum            'C34 H50 Br2 Cl2 N3 P'
_chemical_formula_weight         762.46
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 123.958(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1055(4)
_cell_length_b                   25.0614(9)
_cell_length_c                   14.6620(4)
_cell_measurement_reflns_used    7390
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.76
_cell_measurement_theta_min      2.33
_cell_volume                     3689.5(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_laue_measured_fraction_full 1.000
_diffrn_reflns_laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            36844
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.005
_diffrn_reflns_theta_min         1.625
_diffrn_source                   'fine focus sealed tube'
_exptl_absorpt_coefficient_mu    2.412
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6625
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_description       prism
_exptl_crystal_F_000             1576
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_refine_diff_density_max         1.113
_refine_diff_density_min         -1.015
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         8912
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0934
_refine_ls_R_factor_gt           0.0585
_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)+(0.0581P)²+8.2172P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1313
_refine_ls_wR_factor_ref         0.1487
_reflns_Friedel_coverage         0.000
_reflns_friedel_fraction_full    .
_reflns_friedel_fraction_max     .
_reflns_number_gt                6146
_reflns_number_total             8912
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cc02920a3-4.cif
_cod_data_source_block           pbts150113_a
_cod_database_code               7117351
_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   0.486
_shelx_estimated_absorpt_t_max   0.644
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
C1 C 0.6033(3) 0.73527(15) 0.3774(3) 0.0291(7) Uani 1 1 d . . . . .
H1 H 0.5719 0.7597 0.4075 0.035 Uiso 1 1 calc R U . . .
C2 C 0.7289(4) 0.67729(16) 0.3606(3) 0.0342(8) Uani 1 1 d . . . . .
H2 H 0.8009 0.6545 0.3781 0.041 Uiso 1 1 calc R U . . .
C3 C 0.6161(4) 0.68457(16) 0.2603(3) 0.0354(8) Uani 1 1 d . . . . .
H3 H 0.5938 0.6680 0.1938 0.043 Uiso 1 1 calc R U . . .
C4 C 0.4080(4) 0.74119(16) 0.1868(3) 0.0324(8) Uani 1 1 d . . . . .
C5 C 0.2965(4) 0.71335(18) 0.1648(3) 0.0412(9) Uani 1 1 d . . . . .
C6 C 0.1730(4) 0.7360(2) 0.0874(4) 0.0503(11) Uani 1 1 d . . . . .
H6 H 0.0939 0.7187 0.0708 0.060 Uiso 1 1 calc R U . . .
C7 C 0.1637(4) 0.7828(2) 0.0347(4) 0.0518(12) Uani 1 1 d . . . . .
H7 H 0.0785 0.7976 -0.0171 0.062 Uiso 1 1 calc R U . . .
C8 C 0.2761(5) 0.8084(2) 0.0559(4) 0.0490(11) Uani 1 1 d . . . . .
H8 H 0.2676 0.8404 0.0177 0.059 Uiso 1 1 calc R U . . .
C9 C 0.4032(4) 0.78799(17) 0.1333(3) 0.0413(9) Uani 1 1 d . . . . .
C10 C 0.3041(5) 0.6599(2) 0.2162(5) 0.0579(13) Uani 1 1 d . . . . .
H10 H 0.3987 0.6535 0.2780 0.069 Uiso 1 1 calc R U . . .
C11 C 0.2626(7) 0.6158(2) 0.1302(7) 0.090(2) Uani 1 1 d . . . . .
H11A H 0.1678 0.6196 0.0718 0.135 Uiso 1 1 calc R U . . .
H11B H 0.2782 0.5808 0.1653 0.135 Uiso 1 1 calc R U . . .
H11C H 0.3152 0.6189 0.0984 0.135 Uiso 1 1 calc R U . . .
C12 C 0.2177(6) 0.6580(3) 0.2628(5) 0.0761(18) Uani 1 1 d . . . . .
H12A H 0.2397 0.6884 0.3122 0.114 Uiso 1 1 calc R U . . .
H12B H 0.2350 0.6247 0.3037 0.114 Uiso 1 1 calc R U . . .
H12C H 0.1235 0.6597 0.2023 0.114 Uiso 1 1 calc R U . . .
C13 C 0.5276(5) 0.8169(2) 0.1591(5) 0.0629(14) Uani 1 1 d . . . . .
H13 H 0.6064 0.7937 0.2082 0.075 Uiso 1 1 calc R U . . .
C14 C 0.5457(9) 0.8695(3) 0.2186(6) 0.109(3) Uani 1 1 d . . . . .
H14A H 0.4761 0.8947 0.1678 0.164 Uiso 1 1 calc R U . . .
H14B H 0.6333 0.8846 0.2447 0.164 Uiso 1 1 calc R U . . .
H14C H 0.5392 0.8631 0.2814 0.164 Uiso 1 1 calc R U . . .
C15 C 0.5221(7) 0.8279(3) 0.0534(5) 0.0777(18) Uani 1 1 d . . . . .
H15A H 0.4977 0.7951 0.0099 0.116 Uiso 1 1 calc R U . . .
H15B H 0.6096 0.8401 0.0727 0.116 Uiso 1 1 calc R U . . .
H15C H 0.4555 0.8555 0.0102 0.116 Uiso 1 1 calc R U . . .
C16 C 0.8197(4) 0.71453(16) 0.5492(3) 0.0327(8) Uani 1 1 d . . . . .
C17 C 0.8104(5) 0.75256(19) 0.6121(3) 0.0485(11) Uani 1 1 d . . . . .
H17 H 0.7364 0.7761 0.5815 0.058 Uiso 1 1 calc R U . . .
C18 C 0.9137(5) 0.7550(2) 0.7221(4) 0.0644(14) Uani 1 1 d . . . . .
H18 H 0.9132 0.7812 0.7687 0.077 Uiso 1 1 calc R U . . .
C19 C 1.0171(5) 0.7192(2) 0.7632(4) 0.0616(14) Uani 1 1 d . . . . .
H19 H 1.0882 0.7201 0.8387 0.074 Uiso 1 1 calc R U . . .
C20 C 1.0162(4) 0.68228(19) 0.6940(3) 0.0477(11) Uani 1 1 d . . . . .
C21 C 1.1292(5) 0.6428(2) 0.7345(5) 0.0751(17) Uani 1 1 d . . . . .
H21A H 1.1705 0.6363 0.8138 0.090 Uiso 1 1 calc R U . . .
H21B H 1.1979 0.6590 0.7263 0.090 Uiso 1 1 calc R U . . .
C22 C 0.9536(7) 0.5447(2) 0.6687(5) 0.0717(17) Uani 1 1 d . . . . .
H22 H 0.9841 0.5068 0.6853 0.086 Uiso 1 1 calc R U . A 1
C23 C 0.8125(17) 0.5442(6) 0.5450(14) 0.0873(15) Uani 0.5 1 d . . P B 1
H23A H 0.7733 0.5804 0.5267 0.105 Uiso 0.5 1 calc R U P B 1
H23B H 0.8308 0.5338 0.4895 0.105 Uiso 0.5 1 calc R U P B 1
C24 C 0.7145(16) 0.5052(6) 0.5419(14) 0.0873(15) Uani 0.5 1 d . . P B 1
H24A H 0.7481 0.4683 0.5489 0.105 Uiso 0.5 1 calc R U P B 1
H24B H 0.6280 0.5081 0.4700 0.105 Uiso 0.5 1 calc R U P B 1
C25 C 0.6935(16) 0.5158(6) 0.6348(14) 0.0873(15) Uani 0.5 1 d . . P B 1
H25A H 0.6459 0.5500 0.6206 0.105 Uiso 0.5 1 calc R U P B 1
H25B H 0.6368 0.4872 0.6345 0.105 Uiso 0.5 1 calc R U P B 1
C26 C 0.8196(16) 0.5179(7) 0.7439(15) 0.0873(15) Uani 0.5 1 d . . P B 1
H26A H 0.8617 0.4822 0.7631 0.105 Uiso 0.5 1 calc R U P B 1
H26B H 0.8016 0.5279 0.7997 0.105 Uiso 0.5 1 calc R U P B 1
C27 C 0.9153(15) 0.5587(6) 0.7452(14) 0.0873(15) Uani 0.5 1 d . . P B 1
H27A H 0.8722 0.5943 0.7252 0.105 Uiso 0.5 1 calc R U P B 1
H27B H 0.9966 0.5612 0.8207 0.105 Uiso 0.5 1 calc R U P B 1
C23B C 0.8215(17) 0.5584(6) 0.5899(14) 0.0873(15) Uani 0.5 1 d . . P B 2
H23C H 0.8022 0.5556 0.5149 0.105 Uiso 0.5 1 calc R U P B 2
H23D H 0.8030 0.5954 0.6014 0.105 Uiso 0.5 1 calc R U P B 2
C24B C 0.7359(16) 0.5181(6) 0.6052(14) 0.0873(15) Uani 0.5 1 d . . P B 2
H24C H 0.6402 0.5253 0.5505 0.105 Uiso 0.5 1 calc R U P B 2
H24D H 0.7554 0.4813 0.5935 0.105 Uiso 0.5 1 calc R U P B 2
C25B C 0.7675(16) 0.5234(8) 0.7209(16) 0.0873(15) Uani 0.5 1 d . . P B 2
H25C H 0.7442 0.5599 0.7307 0.105 Uiso 0.5 1 calc R U P B 2
H25D H 0.7121 0.4978 0.7301 0.105 Uiso 0.5 1 calc R U P B 2
C26B C 0.9108(15) 0.5131(6) 0.8068(14) 0.0873(15) Uani 0.5 1 d . . P B 2
H26C H 0.9341 0.4761 0.7999 0.105 Uiso 0.5 1 calc R U P B 2
H26D H 0.9277 0.5172 0.8808 0.105 Uiso 0.5 1 calc R U P B 2
C27B C 0.9953(15) 0.5523(6) 0.7929(13) 0.0873(15) Uani 0.5 1 d . . P B 2
H27C H 1.0912 0.5445 0.8457 0.105 Uiso 0.5 1 calc R U P B 2
H27D H 0.9776 0.5893 0.8051 0.105 Uiso 0.5 1 calc R U P B 2
C28 C 1.2017(11) 0.5271(4) 0.7064(11) 0.063(2) Uani 0.5 1 d . . P C 1
H28 H 1.1643 0.4940 0.6610 0.075 Uiso 0.5 1 calc R U P C 1
C29 C 1.261(2) 0.5176(12) 0.839(2) 0.129(3) Uani 0.5 1 d . . P C 1
H29A H 1.3017 0.5507 0.8816 0.155 Uiso 0.5 1 calc R U P C 1
H29B H 1.1890 0.5061 0.8475 0.155 Uiso 0.5 1 calc R U P C 1
C30 C 1.3681(17) 0.4723(8) 0.8753(16) 0.129(3) Uani 0.5 1 d . . P C 1
H30A H 1.4023 0.4623 0.9521 0.155 Uiso 0.5 1 calc R U P C 1
H30B H 1.3231 0.4405 0.8289 0.155 Uiso 0.5 1 calc R U P C 1
C31 C 1.4631(18) 0.4832(9) 0.8704(17) 0.129(3) Uani 0.5 1 d . . P C 1
H31A H 1.5239 0.4521 0.8956 0.155 Uiso 0.5 1 calc R U P C 1
H31B H 1.5128 0.5134 0.9205 0.155 Uiso 0.5 1 calc R U P C 1
C32 C 1.418(2) 0.4989(10) 0.7482(16) 0.129(3) Uani 0.5 1 d . . P C 1
H32A H 1.3699 0.4687 0.6978 0.155 Uiso 0.5 1 calc R U P C 1
H32B H 1.4978 0.5066 0.7473 0.155 Uiso 0.5 1 calc R U P C 1
C33 C 1.3221(17) 0.5512(9) 0.7067(17) 0.129(3) Uani 0.5 1 d . . P C 1
H33A H 1.3642 0.5814 0.7587 0.155 Uiso 0.5 1 calc R U P C 1
H33B H 1.2951 0.5627 0.6324 0.155 Uiso 0.5 1 calc R U P C 1
C28B C 1.2512(11) 0.5523(4) 0.7351(11) 0.063(2) Uani 0.5 1 d . . P C 2
H28B H 1.3173 0.5822 0.7658 0.075 Uiso 0.5 1 calc R U P C 2
C29B C 1.287(2) 0.5125(11) 0.822(2) 0.129(3) Uani 0.5 1 d . . P C 2
H29C H 1.2061 0.4953 0.8091 0.155 Uiso 0.5 1 calc R U P C 2
H29D H 1.3338 0.5304 0.8950 0.155 Uiso 0.5 1 calc R U P C 2
C30B C 1.3934(19) 0.4640(9) 0.8214(17) 0.129(3) Uani 0.5 1 d . . P C 2
H30C H 1.4542 0.4501 0.8971 0.155 Uiso 0.5 1 calc R U P C 2
H30D H 1.3381 0.4338 0.7743 0.155 Uiso 0.5 1 calc R U P C 2
C31B C 1.4571(19) 0.4798(9) 0.7898(18) 0.129(3) Uani 0.5 1 d . . P C 2
H31C H 1.5149 0.4504 0.7950 0.155 Uiso 0.5 1 calc R U P C 2
H31D H 1.5161 0.5084 0.8402 0.155 Uiso 0.5 1 calc R U P C 2
C32B C 1.3915(18) 0.4985(9) 0.6895(16) 0.129(3) Uani 0.5 1 d . . P C 2
H32C H 1.3722 0.4688 0.6380 0.155 Uiso 0.5 1 calc R U P C 2
H32D H 1.4481 0.5246 0.6831 0.155 Uiso 0.5 1 calc R U P C 2
C33B C 1.2553(18) 0.5265(9) 0.6547(16) 0.129(3) Uani 0.5 1 d . . P C 2
H33C H 1.2323 0.5526 0.5960 0.155 Uiso 0.5 1 calc R U P C 2
H33D H 1.1847 0.4989 0.6223 0.155 Uiso 0.5 1 calc R U P C 2
C34 C 0.8098(8) 0.8922(3) 0.5325(6) 0.092(2) Uani 1 1 d . . . . .
H34A H 0.7199 0.8825 0.5133 0.111 Uiso 1 1 calc R U . . .
H34B H 0.8726 0.8895 0.6133 0.111 Uiso 1 1 calc R U . . .
N1 N 0.7201(3) 0.70945(12) 0.4336(2) 0.0291(6) Uani 1 1 d . . . . .
N2 N 0.5390(3) 0.72083(13) 0.2726(2) 0.0294(6) Uani 1 1 d . . . . .
N3 N 0.9185(3) 0.67968(14) 0.5865(3) 0.0403(8) Uani 1 1 d . . . . .
P1 P 1.07899(14) 0.58007(6) 0.66333(11) 0.0618(4) Uani 1 1 d . . . . .
Br1 Br 0.98232(4) 0.89902(2) 0.85555(4) 0.04471(13) Uani 1 1 d . . . . .
Br2 Br 0.47916(4) 0.83449(2) 0.46548(3) 0.04640(14) Uani 1 1 d . . . . .
Cl1 Cl 0.8083(5) 0.95707(11) 0.4909(2) 0.207(2) Uani 1 1 d . . . . .
Cl2 Cl 0.85916(18) 0.84729(9) 0.46662(17) 0.0984(6) Uani 1 1 d . . . . .
H1P H 1.022(4) 0.5823(17) 0.552(3) 0.045(12) Uiso 1 1 d . . . . .
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N2 C1 N1 108.4(3) . .
N2 C1 H1 125.8 . .
N1 C1 H1 125.8 . .
C3 C2 N1 107.2(3) . .
C3 C2 H2 126.4 . .
N1 C2 H2 126.4 . .
C2 C3 N2 107.0(3) . .
C2 C3 H3 126.5 . .
N2 C3 H3 126.5 . .
C5 C4 C9 124.2(4) . .
C5 C4 N2 118.2(3) . .
C9 C4 N2 117.6(3) . .
C4 C5 C6 116.5(4) . .
C4 C5 C10 123.3(4) . .
C6 C5 C10 120.2(4) . .
C7 C6 C5 121.2(4) . .
C7 C6 H6 119.4 . .
C5 C6 H6 119.4 . .
C6 C7 C8 120.8(4) . .
C6 C7 H7 119.6 . .
C8 C7 H7 119.6 . .
C7 C8 C9 120.9(4) . .
C7 C8 H8 119.6 . .
C9 C8 H8 119.6 . .
C4 C9 C8 116.4(4) . .
C4 C9 C13 122.6(4) . .
C8 C9 C13 121.0(4) . .
C5 C10 C11 109.0(5) . .
C5 C10 C12 112.5(4) . .
C11 C10 C12 110.6(5) . .
C5 C10 H10 108.2 . .
C11 C10 H10 108.2 . .
C12 C10 H10 108.2 . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C10 C12 H12A 109.5 . .
C10 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C10 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C9 C13 C14 111.2(5) . .
C9 C13 C15 110.9(5) . .
C14 C13 C15 109.4(5) . .
C9 C13 H13 108.4 . .
C14 C13 H13 108.4 . .
C15 C13 H13 108.4 . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C13 C15 H15A 109.5 . .
C13 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C13 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
N3 C16 C17 125.0(4) . .
N3 C16 N1 113.4(3) . .
C17 C16 N1 121.6(3) . .
C16 C17 C18 116.9(4) . .
C16 C17 H17 121.5 . .
C18 C17 H17 121.5 . .
C19 C18 C17 119.4(5) . .
C19 C18 H18 120.3 . .
C17 C18 H18 120.3 . .
C20 C19 C18 119.1(4) . .
C20 C19 H19 120.4 . .
C18 C19 H19 120.4 . .
N3 C20 C19 122.7(4) . .
N3 C20 C21 116.0(4) . .
C19 C20 C21 121.3(4) . .
C20 C21 P1 113.9(3) . .
C20 C21 H21A 108.8 . .
P1 C21 H21A 108.8 . .
C20 C21 H21B 108.8 . .
P1 C21 H21B 108.8 . .
H21A C21 H21B 107.7 . .
C23B C22 C27B 113.6(9) . .
C27 C22 C23 105.3(9) . .
C23B C22 P1 116.6(7) . .
C27 C22 P1 123.2(8) . .
C27B C22 P1 104.7(6) . .
C23 C22 P1 109.6(6) . .
C27 C22 H22 105.8 . .
C23 C22 H22 105.8 . .
P1 C22 H22 105.8 . .
C24 C23 C22 110.4(11) . .
C24 C23 H23A 109.6 . .
C22 C23 H23A 109.6 . .
C24 C23 H23B 109.6 . .
C22 C23 H23B 109.6 . .
H23A C23 H23B 108.1 . .
C23 C24 C25 111.9(14) . .
C23 C24 H24A 109.2 . .
C25 C24 H24A 109.2 . .
C23 C24 H24B 109.2 . .
C25 C24 H24B 109.2 . .
H24A C24 H24B 107.9 . .
C26 C25 C24 112.6(13) . .
C26 C25 H25A 109.1 . .
C24 C25 H25A 109.1 . .
C26 C25 H25B 109.1 . .
C24 C25 H25B 109.1 . .
H25A C25 H25B 107.8 . .
C25 C26 C27 110.7(14) . .
C25 C26 H26A 109.5 . .
C27 C26 H26A 109.5 . .
C25 C26 H26B 109.5 . .
C27 C26 H26B 109.5 . .
H26A C26 H26B 108.1 . .
C22 C27 C26 112.7(13) . .
C22 C27 H27A 109.0 . .
C26 C27 H27A 109.0 . .
C22 C27 H27B 109.0 . .
C26 C27 H27B 109.0 . .
H27A C27 H27B 107.8 . .
C22 C23B C24B 105.6(12) . .
C22 C23B H23C 110.6 . .
C24B C23B H23C 110.6 . .
C22 C23B H23D 110.6 . .
C24B C23B H23D 110.6 . .
H23C C23B H23D 108.8 . .
C25B C24B C23B 109.5(14) . .
C25B C24B H24C 109.8 . .
C23B C24B H24C 109.8 . .
C25B C24B H24D 109.8 . .
C23B C24B H24D 109.8 . .
H24C C24B H24D 108.2 . .
C26B C25B C24B 112.1(12) . .
C26B C25B H25C 109.2 . .
C24B C25B H25C 109.2 . .
C26B C25B H25D 109.2 . .
C24B C25B H25D 109.2 . .
H25C C25B H25D 107.9 . .
C25B C26B C27B 109.2(13) . .
C25B C26B H26C 109.8 . .
C27B C26B H26C 109.8 . .
C25B C26B H26D 109.8 . .
C27B C26B H26D 109.8 . .
H26C C26B H26D 108.3 . .
C26B C27B C22 105.6(12) . .
C26B C27B H27C 110.6 . .
C22 C27B H27C 110.6 . .
C26B C27B H27D 110.6 . .
C22 C27B H27D 110.6 . .
H27C C27B H27D 108.8 . .
C33 C28 C29 104.9(14) . .
C33 C28 P1 107.2(9) . .
C29 C28 P1 104.0(9) . .
C33 C28 H28 113.3 . .
C29 C28 H28 113.3 . .
P1 C28 H28 113.3 . .
C30 C29 C28 103.6(14) . .
C30 C29 H29A 111.0 . .
C28 C29 H29A 111.0 . .
C30 C29 H29B 111.0 . .
C28 C29 H29B 111.0 . .
H29A C29 H29B 109.0 . .
C31 C30 C29 116(2) . .
C31 C30 H30A 108.2 . .
C29 C30 H30A 108.2 . .
C31 C30 H30B 108.2 . .
C29 C30 H30B 108.2 . .
H30A C30 H30B 107.4 . .
C30 C31 C32 112.2(18) . .
C30 C31 H31A 109.2 . .
C32 C31 H31A 109.2 . .
C30 C31 H31B 109.2 . .
C32 C31 H31B 109.2 . .
H31A C31 H31B 107.9 . .
C31 C32 C33 109.9(16) . .
C31 C32 H32A 109.7 . .
C33 C32 H32A 109.7 . .
C31 C32 H32B 109.7 . .
C33 C32 H32B 109.7 . .
H32A C32 H32B 108.2 . .
C28 C33 C32 99.2(15) . .
C28 C33 H33A 111.9 . .
C32 C33 H33A 111.9 . .
C28 C33 H33B 111.9 . .
C32 C33 H33B 111.9 . .
H33A C33 H33B 109.6 . .
C33B C28B C29B 106.8(14) . .
C33B C28B P1 104.9(10) . .
C29B C28B P1 115.9(11) . .
C33B C28B H28B 109.7 . .
C29B C28B H28B 109.7 . .
P1 C28B H28B 109.7 . .
C28B C29B C30B 108.7(15) . .
C28B C29B H29C 109.9 . .
C30B C29B H29C 109.9 . .
C28B C29B H29D 109.9 . .
C30B C29B H29D 109.9 . .
H29C C29B H29D 108.3 . .
C31B C30B C29B 114(2) . .
C31B C30B H30C 108.7 . .
C29B C30B H30C 108.7 . .
C31B C30B H30D 108.7 . .
C29B C30B H30D 108.7 . .
H30C C30B H30D 107.6 . .
C30B C31B C32B 117(2) . .
C30B C31B H31C 108.1 . .
C32B C31B H31C 108.1 . .
C30B C31B H31D 108.1 . .
C32B C31B H31D 108.1 . .
H31C C31B H31D 107.3 . .
C31B C32B C33B 112.8(18) . .
C31B C32B H32C 109.0 . .
C33B C32B H32C 109.0 . .
C31B C32B H32D 109.0 . .
C33B C32B H32D 109.0 . .
H32C C32B H32D 107.8 . .
C28B C33B C32B 117.5(15) . .
C28B C33B H33C 107.9 . .
C32B C33B H33C 107.9 . .
C28B C33B H33D 107.9 . .
C32B C33B H33D 107.9 . .
H33C C33B H33D 107.2 . .
Cl1 C34 Cl2 109.9(4) . .
Cl1 C34 H34A 109.7 . .
Cl2 C34 H34A 109.7 . .
Cl1 C34 H34B 109.7 . .
Cl2 C34 H34B 109.7 . .
H34A C34 H34B 108.2 . .
C1 N1 C2 108.3(3) . .
C1 N1 C16 125.8(3) . .
C2 N1 C16 125.9(3) . .
C1 N2 C3 109.1(3) . .
C1 N2 C4 123.7(3) . .
C3 N2 C4 127.1(3) . .
C16 N3 C20 116.8(4) . .
C21 P1 C22 115.2(3) . .
C21 P1 C28 119.4(4) . .
C22 P1 C28 99.9(4) . .
C21 P1 C28B 95.1(4) . .
C22 P1 C28B 119.8(4) . .
C21 P1 H1P 115.9(18) . .
C22 P1 H1P 101.5(18) . .
C28 P1 H1P 102.2(18) . .
C28B P1 H1P 110.2(18) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N2 1.327(5) .
C1 N1 1.340(4) .
C1 H1 0.9500 .
C2 C3 1.348(5) .
C2 N1 1.391(5) .
C2 H2 0.9500 .
C3 N2 1.385(5) .
C3 H3 0.9500 .
C4 C5 1.388(6) .
C4 C9 1.394(6) .
C4 N2 1.459(4) .
C5 C6 1.397(6) .
C5 C10 1.515(6) .
C6 C7 1.373(7) .
C6 H6 0.9500 .
C7 C8 1.374(7) .
C7 H7 0.9500 .
C8 C9 1.402(6) .
C8 H8 0.9500 .
C9 C13 1.516(7) .
C10 C11 1.535(9) .
C10 C12 1.536(7) .
C10 H10 1.0000 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 C14 1.528(9) .
C13 C15 1.539(8) .
C13 H13 1.0000 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 N3 1.328(5) .
C16 C17 1.374(6) .
C16 N1 1.435(4) .
C17 C18 1.384(6) .
C17 H17 0.9500 .
C18 C19 1.375(8) .
C18 H18 0.9500 .
C19 C20 1.369(7) .
C19 H19 0.9500 .
C20 N3 1.344(5) .
C20 C21 1.515(7) .
C21 P1 1.796(6) .
C21 H21A 0.9900 .
C21 H21B 0.9900 .
C22 C23B 1.396(18) .
C22 C27 1.475(14) .
C22 C27B 1.605(16) .
C22 C23 1.657(19) .
C22 P1 1.797(6) .
C22 H22 1.0000 .
C23 C24 1.52(2) .
C23 H23A 0.9900 .
C23 H23B 0.9900 .
C24 C25 1.542(19) .
C24 H24A 0.9900 .
C24 H24B 0.9900 .
C25 C26 1.47(2) .
C25 H25A 0.9900 .
C25 H25B 0.9900 .
C26 C27 1.54(2) .
C26 H26A 0.9900 .
C26 H26B 0.9900 .
C27 H27A 0.9900 .
C27 H27B 0.9900 .
C23B C24B 1.55(2) .
C23B H23C 0.9900 .
C23B H23D 0.9900 .
C24B C25B 1.52(2) .
C24B H24C 0.9900 .
C24B H24D 0.9900 .
C25B C26B 1.49(2) .
C25B H25C 0.9900 .
C25B H25D 0.9900 .
C26B C27B 1.512(19) .
C26B H26C 0.9900 .
C26B H26D 0.9900 .
C27B H27C 0.9900 .
C27B H27D 0.9900 .
C28 C33 1.57(2) .
C28 C29 1.67(3) .
C28 P1 1.822(11) .
C28 H28 1.0000 .
C29 C30 1.58(2) .
C29 H29A 0.9900 .
C29 H29B 0.9900 .
C30 C31 1.22(3) .
C30 H30A 0.9900 .
C30 H30B 0.9900 .
C31 C32 1.60(3) .
C31 H31A 0.9900 .
C31 H31B 0.9900 .
C32 C33 1.63(2) .
C32 H32A 0.9900 .
C32 H32B 0.9900 .
C33 H33A 0.9900 .
C33 H33B 0.9900 .
C28B C33B 1.37(2) .
C28B C29B 1.48(3) .
C28B P1 1.866(11) .
C28B H28B 1.0000 .
C29B C30B 1.77(2) .
C29B H29C 0.9900 .
C29B H29D 0.9900 .
C30B C31B 1.17(3) .
C30B H30C 0.9900 .
C30B H30D 0.9900 .
C31B C32B 1.31(2) .
C31B H31C 0.9900 .
C31B H31D 0.9900 .
C32B C33B 1.59(2) .
C32B H32C 0.9900 .
C32B H32D 0.9900 .
C33B H33C 0.9900 .
C33B H33D 0.9900 .
C34 Cl1 1.732(7) .
C34 Cl2 1.790(8) .
C34 H34A 0.9900 .
C34 H34B 0.9900 .
P1 H1P 1.38(4) .
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
N1 C2 C3 N2 -0.3(4) . . . .
C9 C4 C5 C6 -3.1(6) . . . .
N2 C4 C5 C6 175.9(4) . . . .
C9 C4 C5 C10 174.0(4) . . . .
N2 C4 C5 C10 -7.0(6) . . . .
C4 C5 C6 C7 1.3(7) . . . .
C10 C5 C6 C7 -175.9(5) . . . .
C5 C6 C7 C8 0.7(7) . . . .
C6 C7 C8 C9 -1.1(7) . . . .
C5 C4 C9 C8 2.7(6) . . . .
N2 C4 C9 C8 -176.3(4) . . . .
C5 C4 C9 C13 -179.4(4) . . . .
N2 C4 C9 C13 1.6(6) . . . .
C7 C8 C9 C4 -0.5(7) . . . .
C7 C8 C9 C13 -178.4(5) . . . .
C4 C5 C10 C11 -104.9(5) . . . .
C6 C5 C10 C11 72.2(6) . . . .
C4 C5 C10 C12 132.1(5) . . . .
C6 C5 C10 C12 -50.9(7) . . . .
C4 C9 C13 C14 -109.5(6) . . . .
C8 C9 C13 C14 68.2(6) . . . .
C4 C9 C13 C15 128.5(5) . . . .
C8 C9 C13 C15 -53.7(7) . . . .
N3 C16 C17 C18 1.2(7) . . . .
N1 C16 C17 C18 -178.2(4) . . . .
C16 C17 C18 C19 -1.6(8) . . . .
C17 C18 C19 C20 0.7(9) . . . .
C18 C19 C20 N3 0.6(8) . . . .
C18 C19 C20 C21 178.5(5) . . . .
N3 C20 C21 P1 -32.6(6) . . . .
C19 C20 C21 P1 149.4(5) . . . .
C23B C22 C23 C24 -81(2) . . . .
C27 C22 C23 C24 -57.4(12) . . . .
C27B C22 C23 C24 -52.5(17) . . . .
P1 C22 C23 C24 168.2(8) . . . .
C22 C23 C24 C25 53.2(14) . . . .
C23 C24 C25 C26 -52.8(17) . . . .
C24 C25 C26 C27 54.2(18) . . . .
C23B C22 C27 C26 70.7(14) . . . .
C27B C22 C27 C26 -112(2) . . . .
C23 C22 C27 C26 61.1(14) . . . .
P1 C22 C27 C26 -172.3(9) . . . .
C25 C26 C27 C22 -62.7(17) . . . .
C27 C22 C23B C24B -62.6(12) . . . .
C27B C22 C23B C24B -64.3(14) . . . .
C23 C22 C23B C24B 95(3) . . . .
P1 C22 C23B C24B 173.8(8) . . . .
C22 C23B C24B C25B 60.3(14) . . . .
C23B C24B C25B C26B -59.3(17) . . . .
C24B C25B C26B C27B 59.0(18) . . . .
C25B C26B C27B C22 -56.1(14) . . . .
C23B C22 C27B C26B 64.2(13) . . . .
C27 C22 C27B C26B 60.9(17) . . . .
C23 C22 C27B C26B 51.8(16) . . . .
P1 C22 C27B C26B -167.6(8) . . . .
C33 C28 C29 C30 -67(2) . . . .
P1 C28 C29 C30 -179.3(15) . . . .
C28 C29 C30 C31 63(3) . . . .
C29 C30 C31 C32 -59(3) . . . .
C30 C31 C32 C33 61(3) . . . .
C29 C28 C33 C32 69.0(17) . . . .
P1 C28 C33 C32 179.2(11) . . . .
C31 C32 C33 C28 -64(2) . . . .
C33B C28B C29B C30B 28(2) . . . .
P1 C28B C29B C30B 144.7(14) . . . .
C28B C29B C30B C31B 28(3) . . . .
C29B C30B C31B C32B -60(3) . . . .
C30B C31B C32B C33B 33(3) . . . .
C29B C28B C33B C32B -57(2) . . . .
P1 C28B C33B C32B 179.4(16) . . . .
C31B C32B C33B C28B 33(3) . . . .
N2 C1 N1 C2 -0.2(4) . . . .
N2 C1 N1 C16 179.3(3) . . . .
C3 C2 N1 C1 0.3(4) . . . .
C3 C2 N1 C16 -179.1(4) . . . .
N3 C16 N1 C1 172.2(3) . . . .
C17 C16 N1 C1 -8.3(6) . . . .
N3 C16 N1 C2 -8.5(5) . . . .
C17 C16 N1 C2 171.1(4) . . . .
N1 C1 N2 C3 0.0(4) . . . .
N1 C1 N2 C4 -179.8(3) . . . .
C2 C3 N2 C1 0.2(4) . . . .
C2 C3 N2 C4 179.9(3) . . . .
C5 C4 N2 C1 -90.8(5) . . . .
C9 C4 N2 C1 88.3(5) . . . .
C5 C4 N2 C3 89.5(5) . . . .
C9 C4 N2 C3 -91.5(5) . . . .
C17 C16 N3 C20 0.0(6) . . . .
N1 C16 N3 C20 179.5(4) . . . .
C19 C20 N3 C16 -1.0(7) . . . .
C21 C20 N3 C16 -179.0(4) . . . .
C20 C21 P1 C22 -58.3(5) . . . .
C20 C21 P1 C28 -177.2(6) . . . .
C20 C21 P1 C28B 175.3(6) . . . .
C23B C22 P1 C21 85.4(9) . . . .
C27 C22 P1 C21 -13.5(9) . . . .
C27B C22 P1 C21 -41.0(7) . . . .
C23 C22 P1 C21 111.2(6) . . . .
C23B C22 P1 C28 -145.4(9) . . . .
C27 C22 P1 C28 115.8(9) . . . .
C27B C22 P1 C28 88.2(7) . . . .
C23 C22 P1 C28 -119.6(8) . . . .
C23B C22 P1 C28B -162.1(9) . . . .
C27 C22 P1 C28B 99.1(10) . . . .
C27B C22 P1 C28B 71.5(8) . . . .
C23 C22 P1 C28B -136.3(8) . . . .
C33 C28 P1 C21 -53.5(13) . . . .
C29 C28 P1 C21 57.3(13) . . . .
C33 C28 P1 C22 -179.9(11) . . . .
C29 C28 P1 C22 -69.2(13) . . . .
C33 C28 P1 C28B -35.7(14) . . . .
C29 C28 P1 C28B 75.1(19) . . . .
C33B C28B P1 C21 -139.2(13) . . . .
C29B C28B P1 C21 103.4(15) . . . .
C33B C28B P1 C22 97.8(13) . . . .
C29B C28B P1 C22 -19.6(16) . . . .
C33B C28B P1 C28 56.3(16) . . . .
C29B C28B P1 C28 -61.1(19) . . . .
_cod_duplicate_entry 7117348
