#------------------------------------------------------------------------------
#$Date: 2024-10-06 12:02:58 +0300 (Sun, 06 Oct 2024) $
#$Revision: 295301 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/34/7063434.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_7063434
loop_
_publ_author_name
'Pei, Jiaqi'
'Tang, Tiantian'
'Zhang, Jianing'
'Qin, Yunlong'
'Cheng, Pengfei'
'Wang, Qilin'
_publ_section_title
;
 Diastereoselective dearomative bifunctionalization of isoquinolinium
 salts to access bridged tetrahydroisoquinolines
;
_journal_issue                   37
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              16151
_journal_page_last               16154
_journal_paper_doi               10.1039/D4NJ02968B
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C41 H41 N2 O P'
_chemical_formula_sum            'C41 H41 N2 O P'
_chemical_formula_weight         608.73
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-04-16
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2024-06-13 deposited with the CCDC.	2024-09-02 downloaded from the CCDC.
;
_cell_angle_alpha                111.600(6)
_cell_angle_beta                 93.776(5)
_cell_angle_gamma                104.186(6)
_cell_formula_units_Z            2
_cell_length_a                   11.0596(7)
_cell_length_b                   11.2945(8)
_cell_length_c                   15.3318(9)
_cell_measurement_reflns_used    4385
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      73.1190
_cell_measurement_theta_min      3.1040
_cell_volume                     1700.3(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -26.00   1.00   1.00    1.00    --   41.11 -77.00   0.00   27
  2  ω      1.00  58.00   1.00    1.00    --   41.11 -99.00   0.00   57
  3  ω     66.00 109.00   1.00    1.00    --  106.95 -94.00 120.00   43
  4  ω     39.00 126.00   1.00    1.00    --  106.95 -45.00  60.00   87
  5  ω    111.00 178.00   1.00    1.00    --  106.95  30.00 120.00   67
  6  ω    122.00 169.00   1.00    1.00    --  106.95 125.00 -30.00   47
  7  ω    100.00 173.00   1.00    1.00    --  106.95 125.00  60.00   73
  8  ω     79.00 178.00   1.00    1.00    --  106.95  30.00-120.00   99
  9  ω     87.00 148.00   1.00    1.00    --  106.95  45.00-180.00   61
 10  ω     75.00 114.00   1.00    1.00    --  106.95  77.00  30.00   39
 11  ω     33.00  86.00   1.00    1.00    --  106.95 -30.00 -60.00   53
 12  ω     28.00  95.00   1.00    1.00    --  106.95 -94.00   0.00   67
 13  ω     36.00 119.00   1.00    1.00    --  106.95-125.00 -60.00   83
 14  ω     54.00  97.00   1.00    1.00    --   41.11-125.00-180.00   43
 15  ω     36.00 114.00   1.00    1.00    --  106.95-125.00 120.00   78
 16  ω    -48.00  -9.00   1.00    1.00    --  -41.11 125.00   0.00   39
 17  ω   -112.00 -13.00   1.00    1.00    --  -41.11 -57.00 120.00   99
 18  ω   -112.00 -17.00   1.00    1.00    --  -41.11 -38.00-150.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0244049000
_diffrn_orient_matrix_UB_12      -0.1236611000
_diffrn_orient_matrix_UB_13      -0.0742027000
_diffrn_orient_matrix_UB_21      0.1246810000
_diffrn_orient_matrix_UB_22      0.0264331000
_diffrn_orient_matrix_UB_23      0.0646313000
_diffrn_orient_matrix_UB_31      -0.0716860000
_diffrn_orient_matrix_UB_32      -0.0866563000
_diffrn_orient_matrix_UB_33      0.0485202000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0618
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11982
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.218
_diffrn_reflns_theta_min         3.148
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.970
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62417
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0020(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     413
_refine_ls_number_reflns         6613
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0655
_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)+(0.0915P)²+0.3471P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1714
_refine_ls_wR_factor_ref         0.1980
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4796
_reflns_number_total             6613
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4nj02968b3.cif
_cod_data_source_block           pqj-9
_cod_depositor_comments          'Adding full bibliography for 7063434.cif.'
_cod_database_code               7063434
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C11(H11), C40(H40)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C12(H12A,H12B), C13(H13A,H13B), C32(H32A,H32B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C4(H4), C5(H5), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19),
 C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C27(H27), C28(H28), C29(H29),
  C30(H30), C31(H31), C34(H34), C35(H35), C36(H36), C37(H37), C38(H38)
2.d Idealised Me refined as rotating group:
 C39(H39A,H39B,H39C), C41(H41A,H41B,H41C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.502
_oxdiff_exptl_absorpt_empirical_full_min 0.580
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
P1 P 0.80797(6) 0.17638(6) 0.64354(5) 0.0411(2) Uani 1 1 d . . . . .
O1 O 0.76804(18) 0.02799(18) 0.59819(15) 0.0544(5) Uani 1 1 d . . . . .
N1 N 0.65981(19) 0.45498(19) 0.59892(15) 0.0408(5) Uani 1 1 d . . . . .
N2 N 0.5270(2) 0.0887(2) 0.62091(17) 0.0472(5) Uani 1 1 d . . . . .
H2 H 0.580(3) 0.044(3) 0.626(2) 0.055(8) Uiso 1 1 d . . . . .
C1 C 0.6768(2) 0.3021(2) 0.41398(19) 0.0427(6) Uani 1 1 d . . . . .
C2 C 0.6878(3) 0.2471(3) 0.3175(2) 0.0536(7) Uani 1 1 d . . . . .
H2A H 0.769575 0.249792 0.301304 0.064 Uiso 1 1 calc R U . . .
C3 C 0.5828(3) 0.1886(3) 0.2449(2) 0.0607(8) Uani 1 1 d . . . . .
C4 C 0.4640(3) 0.1837(3) 0.2705(2) 0.0625(8) Uani 1 1 d . . . . .
H4 H 0.390457 0.141510 0.222609 0.075 Uiso 1 1 calc R U . . .
C5 C 0.4520(3) 0.2393(3) 0.3647(2) 0.0522(7) Uani 1 1 d . . . . .
H5 H 0.369849 0.234960 0.380578 0.063 Uiso 1 1 calc R U . . .
C6 C 0.5570(2) 0.3017(2) 0.43699(18) 0.0421(6) Uani 1 1 d . . . . .
C7 C 0.5396(2) 0.3652(2) 0.53921(18) 0.0404(5) Uani 1 1 d . . . . .
H7 H 0.479833 0.419440 0.541012 0.048 Uiso 1 1 calc R U . . .
C8 C 0.4800(2) 0.2588(3) 0.57605(19) 0.0428(6) Uani 1 1 d . . . . .
H8A H 0.443085 0.299499 0.632814 0.051 Uiso 1 1 calc R U . . .
H8B H 0.410735 0.188098 0.526363 0.051 Uiso 1 1 calc R U . . .
C9 C 0.5766(2) 0.1979(2) 0.60187(17) 0.0386(5) Uani 1 1 d . . . . .
C10 C 0.7014(2) 0.2511(2) 0.60653(17) 0.0386(5) Uani 1 1 d . . . . .
C11 C 0.7524(2) 0.3789(2) 0.58947(18) 0.0395(5) Uani 1 1 d . . . . .
H11 H 0.829205 0.436256 0.638970 0.047 Uiso 1 1 calc R U . . .
C12 C 0.7901(2) 0.3575(3) 0.49168(19) 0.0463(6) Uani 1 1 d . . . . .
H12A H 0.841807 0.443457 0.493147 0.056 Uiso 1 1 calc R U . . .
H12B H 0.842695 0.295562 0.477613 0.056 Uiso 1 1 calc R U . . .
C13 C 0.6462(3) 0.5234(3) 0.6977(2) 0.0491(6) Uani 1 1 d . . . . .
H13A H 0.633460 0.459312 0.728608 0.059 Uiso 1 1 calc R U . . .
H13B H 0.569581 0.553972 0.698085 0.059 Uiso 1 1 calc R U . . .
C14 C 0.7577(3) 0.6404(3) 0.7547(2) 0.0548(7) Uani 1 1 d . . . . .
C15 C 0.7734(4) 0.6894(4) 0.8539(3) 0.0787(10) Uani 1 1 d . . . . .
H15 H 0.715226 0.645409 0.882895 0.094 Uiso 1 1 calc R U . . .
C16 C 0.8694(5) 0.7980(5) 0.9099(3) 0.1067(15) Uani 1 1 d . . . . .
H16 H 0.877450 0.830123 0.977296 0.128 Uiso 1 1 calc R U . . .
C17 C 0.9544(5) 0.8610(5) 0.8691(4) 0.1091(17) Uani 1 1 d . . . . .
H17 H 1.022191 0.936694 0.908191 0.131 Uiso 1 1 calc R U . . .
C18 C 0.9423(4) 0.8150(4) 0.7704(3) 0.0892(12) Uani 1 1 d . . . . .
H18 H 1.001773 0.858809 0.742029 0.107 Uiso 1 1 calc R U . . .
C19 C 0.8430(3) 0.7047(3) 0.7138(3) 0.0639(8) Uani 1 1 d . . . . .
H19 H 0.833750 0.673456 0.646455 0.077 Uiso 1 1 calc R U . . .
C20 C 0.9621(2) 0.2461(3) 0.6204(2) 0.0459(6) Uani 1 1 d . . . . .
C21 C 1.0426(3) 0.3698(3) 0.6783(3) 0.0619(8) Uani 1 1 d . . . . .
H21 H 1.020239 0.422176 0.735646 0.074 Uiso 1 1 calc R U . . .
C22 C 1.1565(3) 0.4173(4) 0.6521(3) 0.0822(12) Uani 1 1 d . . . . .
H22 H 1.212505 0.502361 0.691412 0.099 Uiso 1 1 calc R U . . .
C23 C 1.1876(4) 0.3404(5) 0.5688(4) 0.0870(13) Uani 1 1 d . . . . .
H23 H 1.263938 0.374529 0.549695 0.104 Uiso 1 1 calc R U . . .
C24 C 1.1119(4) 0.2176(4) 0.5138(3) 0.0814(12) Uani 1 1 d . . . . .
H24 H 1.136694 0.164252 0.457963 0.098 Uiso 1 1 calc R U . . .
C25 C 0.9982(3) 0.1696(3) 0.5388(2) 0.0621(8) Uani 1 1 d . . . . .
H25 H 0.944245 0.083359 0.499561 0.075 Uiso 1 1 calc R U . . .
C26 C 0.8244(2) 0.2316(3) 0.7717(2) 0.0477(6) Uani 1 1 d . . . . .
C27 C 0.8287(3) 0.3588(4) 0.8318(2) 0.0650(8) Uani 1 1 d . . . . .
H27 H 0.820155 0.421571 0.806063 0.078 Uiso 1 1 calc R U . . .
C28 C 0.8454(4) 0.3957(5) 0.9296(3) 0.0885(12) Uani 1 1 d . . . . .
H28 H 0.849060 0.483868 0.970477 0.106 Uiso 1 1 calc R U . . .
C29 C 0.8565(5) 0.3055(6) 0.9677(3) 0.1045(15) Uani 1 1 d . . . . .
H29 H 0.868681 0.331042 1.034745 0.125 Uiso 1 1 calc R U . . .
C30 C 0.8501(4) 0.1797(6) 0.9089(3) 0.0997(14) Uani 1 1 d . . . . .
H30 H 0.855940 0.117009 0.935410 0.120 Uiso 1 1 calc R U . . .
C31 C 0.8351(3) 0.1405(4) 0.8110(3) 0.0685(9) Uani 1 1 d . . . . .
H31 H 0.832223 0.052199 0.770943 0.082 Uiso 1 1 calc R U . . .
C32 C 0.3987(3) 0.0485(3) 0.6363(2) 0.0515(7) Uani 1 1 d . . . . .
H32A H 0.381487 -0.041231 0.637326 0.062 Uiso 1 1 calc R U . . .
H32B H 0.340199 0.041588 0.581816 0.062 Uiso 1 1 calc R U . . .
C33 C 0.3703(3) 0.1412(3) 0.7272(2) 0.0548(7) Uani 1 1 d . . . . .
C34 C 0.4630(4) 0.2188(4) 0.8062(3) 0.0758(10) Uani 1 1 d . . . . .
H34 H 0.547554 0.214785 0.803722 0.091 Uiso 1 1 calc R U . . .
C35 C 0.4351(6) 0.3019(5) 0.8884(3) 0.1110(16) Uani 1 1 d . . . . .
H35 H 0.500156 0.355506 0.942101 0.133 Uiso 1 1 calc R U . . .
C36 C 0.3127(7) 0.3070(6) 0.8927(4) 0.131(2) Uani 1 1 d . . . . .
H36 H 0.293122 0.363757 0.949645 0.157 Uiso 1 1 calc R U . . .
C37 C 0.2193(6) 0.2311(7) 0.8157(4) 0.124(2) Uani 1 1 d . . . . .
H37 H 0.134829 0.235070 0.818743 0.149 Uiso 1 1 calc R U . . .
C38 C 0.2485(4) 0.1484(5) 0.7332(3) 0.0881(13) Uani 1 1 d . . . . .
H38 H 0.183177 0.095498 0.679599 0.106 Uiso 1 1 calc R U . . .
C39 C 0.5802(5) 0.2311(5) 0.0967(3) 0.1137(17) Uani 1 1 d . . . . .
H39A H 0.497727 0.247976 0.102789 0.171 Uiso 1 1 calc R U . . .
H39B H 0.587243 0.194081 0.029180 0.171 Uiso 1 1 calc R U . . .
H39C H 0.647804 0.314674 0.130050 0.171 Uiso 1 1 calc R U . . .
C40 C 0.5921(4) 0.1337(4) 0.1397(3) 0.0844(11) Uani 1 1 d . . . . .
H40 H 0.513334 0.057639 0.109202 0.101 Uiso 1 1 calc R U . . .
C41 C 0.6948(5) 0.0747(5) 0.1150(3) 0.1123(17) Uani 1 1 d . . . . .
H41A H 0.775999 0.144576 0.139237 0.168 Uiso 1 1 calc R U . . .
H41B H 0.684374 0.030078 0.045541 0.168 Uiso 1 1 calc R U . . .
H41C H 0.693113 0.009676 0.143424 0.168 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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
O1 P1 C10 114.36(11) . . ?
O1 P1 C20 111.49(12) . . ?
O1 P1 C26 109.75(12) . . ?
C10 P1 C20 107.28(11) . . ?
C10 P1 C26 107.69(12) . . ?
C26 P1 C20 105.85(13) . . ?
C7 N1 C11 108.42(19) . . ?
C7 N1 C13 112.2(2) . . ?
C13 N1 C11 113.15(19) . . ?
C9 N2 H2 115(2) . . ?
C9 N2 C32 124.3(2) . . ?
C32 N2 H2 120.2(19) . . ?
C2 C1 C12 121.5(2) . . ?
C6 C1 C2 118.6(2) . . ?
C6 C1 C12 119.9(2) . . ?
C1 C2 H2A 118.9 . . ?
C3 C2 C1 122.2(3) . . ?
C3 C2 H2A 118.9 . . ?
C2 C3 C40 123.3(3) . . ?
C4 C3 C2 117.8(3) . . ?
C4 C3 C40 118.9(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.7(3) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.5(3) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C7 121.1(2) . . ?
C5 C6 C1 119.1(2) . . ?
C5 C6 C7 119.7(2) . . ?
N1 C7 C6 110.3(2) . . ?
N1 C7 H7 107.8 . . ?
N1 C7 C8 111.93(19) . . ?
C6 C7 H7 107.8 . . ?
C6 C7 C8 110.9(2) . . ?
C8 C7 H7 107.8 . . ?
C7 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 C7 111.4(2) . . ?
C9 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
N2 C9 C8 114.5(2) . . ?
C10 C9 N2 124.3(2) . . ?
C10 C9 C8 121.2(2) . . ?
C9 C10 P1 117.53(17) . . ?
C9 C10 C11 121.9(2) . . ?
C11 C10 P1 120.33(17) . . ?
N1 C11 C10 112.03(19) . . ?
N1 C11 H11 107.8 . . ?
N1 C11 C12 105.89(18) . . ?
C10 C11 H11 107.8 . . ?
C12 C11 C10 115.1(2) . . ?
C12 C11 H11 107.8 . . ?
C1 C12 C11 112.1(2) . . ?
C1 C12 H12A 109.2 . . ?
C1 C12 H12B 109.2 . . ?
C11 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
N1 C13 H13A 108.8 . . ?
N1 C13 H13B 108.8 . . ?
N1 C13 C14 113.6(2) . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C15 C14 C13 118.7(3) . . ?
C19 C14 C13 122.9(3) . . ?
C19 C14 C15 118.4(3) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 C14 121.8(4) . . ?
C16 C15 H15 119.1 . . ?
C15 C16 H16 120.2 . . ?
C15 C16 C17 119.6(5) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.4(4) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 120.3 . . ?
C19 C18 C17 119.4(4) . . ?
C19 C18 H18 120.3 . . ?
C14 C19 C18 120.4(4) . . ?
C14 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C21 C20 P1 123.9(2) . . ?
C21 C20 C25 119.3(3) . . ?
C25 C20 P1 116.7(2) . . ?
C20 C21 H21 120.2 . . ?
C20 C21 C22 119.6(3) . . ?
C22 C21 H21 120.2 . . ?
C21 C22 H22 120.2 . . ?
C23 C22 C21 119.5(4) . . ?
C23 C22 H22 120.2 . . ?
C22 C23 H23 119.4 . . ?
C24 C23 C22 121.2(3) . . ?
C24 C23 H23 119.4 . . ?
C23 C24 H24 120.1 . . ?
C23 C24 C25 119.7(4) . . ?
C25 C24 H24 120.1 . . ?
C20 C25 H25 119.8 . . ?
C24 C25 C20 120.5(3) . . ?
C24 C25 H25 119.8 . . ?
C27 C26 P1 123.5(2) . . ?
C27 C26 C31 118.8(3) . . ?
C31 C26 P1 117.7(2) . . ?
C26 C27 H27 119.7 . . ?
C26 C27 C28 120.6(3) . . ?
C28 C27 H27 119.7 . . ?
C27 C28 H28 119.9 . . ?
C29 C28 C27 120.3(4) . . ?
C29 C28 H28 119.9 . . ?
C28 C29 H29 120.3 . . ?
C30 C29 C28 119.5(4) . . ?
C30 C29 H29 120.3 . . ?
C29 C30 H30 119.2 . . ?
C29 C30 C31 121.5(4) . . ?
C31 C30 H30 119.2 . . ?
C26 C31 H31 120.3 . . ?
C30 C31 C26 119.4(4) . . ?
C30 C31 H31 120.3 . . ?
N2 C32 H32A 108.6 . . ?
N2 C32 H32B 108.6 . . ?
N2 C32 C33 114.6(2) . . ?
H32A C32 H32B 107.6 . . ?
C33 C32 H32A 108.6 . . ?
C33 C32 H32B 108.6 . . ?
C34 C33 C32 121.9(3) . . ?
C38 C33 C32 120.0(3) . . ?
C38 C33 C34 118.1(3) . . ?
C33 C34 H34 119.4 . . ?
C35 C34 C33 121.1(4) . . ?
C35 C34 H34 119.4 . . ?
C34 C35 H35 120.2 . . ?
C36 C35 C34 119.6(5) . . ?
C36 C35 H35 120.2 . . ?
C35 C36 H36 119.8 . . ?
C37 C36 C35 120.4(5) . . ?
C37 C36 H36 119.8 . . ?
C36 C37 H37 120.3 . . ?
C36 C37 C38 119.5(4) . . ?
C38 C37 H37 120.3 . . ?
C33 C38 C37 121.2(4) . . ?
C33 C38 H38 119.4 . . ?
C37 C38 H38 119.4 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C40 C39 H39A 109.5 . . ?
C40 C39 H39B 109.5 . . ?
C40 C39 H39C 109.5 . . ?
C3 C40 H40 104.5 . . ?
C39 C40 C3 110.8(3) . . ?
C39 C40 H40 104.5 . . ?
C41 C40 C3 116.1(3) . . ?
C41 C40 C39 115.0(4) . . ?
C41 C40 H40 104.5 . . ?
C40 C41 H41A 109.5 . . ?
C40 C41 H41B 109.5 . . ?
C40 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
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
P1 O1 1.4921(19) . ?
P1 C10 1.782(2) . ?
P1 C20 1.811(3) . ?
P1 C26 1.810(3) . ?
N1 C7 1.459(3) . ?
N1 C11 1.472(3) . ?
N1 C13 1.462(3) . ?
N2 H2 0.88(3) . ?
N2 C9 1.365(3) . ?
N2 C32 1.442(3) . ?
C1 C2 1.404(4) . ?
C1 C6 1.393(3) . ?
C1 C12 1.500(4) . ?
C2 H2A 0.9500 . ?
C2 C3 1.392(4) . ?
C3 C4 1.389(5) . ?
C3 C40 1.520(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.377(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(4) . ?
C6 C7 1.513(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.536(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.509(3) . ?
C9 C10 1.349(3) . ?
C10 C11 1.539(3) . ?
C11 H11 1.0000 . ?
C11 C12 1.531(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.496(4) . ?
C14 C15 1.395(4) . ?
C14 C19 1.374(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.355(6) . ?
C16 H16 0.9500 . ?
C16 C17 1.363(7) . ?
C17 H17 0.9500 . ?
C17 C18 1.392(6) . ?
C18 H18 0.9500 . ?
C18 C19 1.385(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.380(4) . ?
C20 C25 1.382(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.389(5) . ?
C22 H22 0.9500 . ?
C22 C23 1.376(6) . ?
C23 H23 0.9500 . ?
C23 C24 1.346(6) . ?
C24 H24 0.9500 . ?
C24 C25 1.381(5) . ?
C25 H25 0.9500 . ?
C26 C27 1.379(4) . ?
C26 C31 1.394(4) . ?
C27 H27 0.9500 . ?
C27 C28 1.386(5) . ?
C28 H28 0.9500 . ?
C28 C29 1.373(6) . ?
C29 H29 0.9500 . ?
C29 C30 1.354(7) . ?
C30 H30 0.9500 . ?
C30 C31 1.385(5) . ?
C31 H31 0.9500 . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C32 C33 1.510(4) . ?
C33 C34 1.379(5) . ?
C33 C38 1.377(4) . ?
C34 H34 0.9500 . ?
C34 C35 1.374(5) . ?
C35 H35 0.9500 . ?
C35 C36 1.373(8) . ?
C36 H36 0.9500 . ?
C36 C37 1.362(8) . ?
C37 H37 0.9500 . ?
C37 C38 1.381(6) . ?
C38 H38 0.9500 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C39 C40 1.502(5) . ?
C40 H40 1.0000 . ?
C40 C41 1.456(6) . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
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
P1 C10 C11 N1 -156.21(17) . . . . ?
P1 C10 C11 C12 82.7(2) . . . . ?
P1 C20 C21 C22 -176.9(2) . . . . ?
P1 C20 C25 C24 177.3(2) . . . . ?
P1 C26 C27 C28 -178.0(3) . . . . ?
P1 C26 C31 C30 178.9(3) . . . . ?
O1 P1 C10 C9 44.7(2) . . . . ?
O1 P1 C10 C11 -140.53(19) . . . . ?
O1 P1 C20 C21 -155.1(2) . . . . ?
O1 P1 C20 C25 25.9(2) . . . . ?
O1 P1 C26 C27 -163.1(2) . . . . ?
O1 P1 C26 C31 17.9(3) . . . . ?
N1 C7 C8 C9 -45.6(3) . . . . ?
N1 C11 C12 C1 -50.6(3) . . . . ?
N1 C13 C14 C15 -161.6(2) . . . . ?
N1 C13 C14 C19 20.8(4) . . . . ?
N2 C9 C10 P1 -2.0(3) . . . . ?
N2 C9 C10 C11 -176.7(2) . . . . ?
N2 C32 C33 C34 -27.5(4) . . . . ?
N2 C32 C33 C38 153.4(3) . . . . ?
C1 C2 C3 C4 -1.2(4) . . . . ?
C1 C2 C3 C40 177.2(3) . . . . ?
C1 C6 C7 N1 17.1(3) . . . . ?
C1 C6 C7 C8 -107.5(2) . . . . ?
C2 C1 C6 C5 4.2(3) . . . . ?
C2 C1 C6 C7 -177.1(2) . . . . ?
C2 C1 C12 C11 -165.5(2) . . . . ?
C2 C3 C4 C5 2.3(4) . . . . ?
C2 C3 C40 C39 -99.7(4) . . . . ?
C2 C3 C40 C41 33.8(5) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
C4 C3 C40 C39 78.7(5) . . . . ?
C4 C3 C40 C41 -147.8(4) . . . . ?
C4 C5 C6 C1 -3.2(4) . . . . ?
C4 C5 C6 C7 178.1(2) . . . . ?
C5 C6 C7 N1 -164.2(2) . . . . ?
C5 C6 C7 C8 71.2(3) . . . . ?
C6 C1 C2 C3 -2.1(4) . . . . ?
C6 C1 C12 C11 13.0(3) . . . . ?
C6 C7 C8 C9 78.1(3) . . . . ?
C7 N1 C11 C10 -51.5(3) . . . . ?
C7 N1 C11 C12 74.8(2) . . . . ?
C7 N1 C13 C14 -165.0(2) . . . . ?
C7 C8 C9 N2 -170.2(2) . . . . ?
C7 C8 C9 C10 10.7(3) . . . . ?
C8 C9 C10 P1 176.90(18) . . . . ?
C8 C9 C10 C11 2.2(4) . . . . ?
C9 N2 C32 C33 -68.3(3) . . . . ?
C9 C10 C11 N1 18.3(3) . . . . ?
C9 C10 C11 C12 -102.8(3) . . . . ?
C10 P1 C20 C21 79.0(3) . . . . ?
C10 P1 C20 C25 -100.0(2) . . . . ?
C10 P1 C26 C27 -38.1(3) . . . . ?
C10 P1 C26 C31 143.0(2) . . . . ?
C10 C11 C12 C1 73.7(3) . . . . ?
C11 N1 C7 C6 -56.9(2) . . . . ?
C11 N1 C7 C8 67.0(2) . . . . ?
C11 N1 C13 C14 71.9(3) . . . . ?
C12 C1 C2 C3 176.4(2) . . . . ?
C12 C1 C6 C5 -174.3(2) . . . . ?
C12 C1 C6 C7 4.4(3) . . . . ?
C13 N1 C7 C6 177.37(18) . . . . ?
C13 N1 C7 C8 -58.7(2) . . . . ?
C13 N1 C11 C10 73.6(3) . . . . ?
C13 N1 C11 C12 -160.1(2) . . . . ?
C13 C14 C15 C16 -177.5(4) . . . . ?
C13 C14 C19 C18 178.1(3) . . . . ?
C14 C15 C16 C17 -0.8(7) . . . . ?
C15 C14 C19 C18 0.4(5) . . . . ?
C15 C16 C17 C18 0.5(8) . . . . ?
C16 C17 C18 C19 0.2(7) . . . . ?
C17 C18 C19 C14 -0.7(6) . . . . ?
C19 C14 C15 C16 0.3(5) . . . . ?
C20 P1 C10 C9 168.9(2) . . . . ?
C20 P1 C10 C11 -16.3(2) . . . . ?
C20 P1 C26 C27 76.4(3) . . . . ?
C20 P1 C26 C31 -102.5(2) . . . . ?
C20 C21 C22 C23 0.0(5) . . . . ?
C21 C20 C25 C24 -1.7(4) . . . . ?
C21 C22 C23 C24 -2.5(6) . . . . ?
C22 C23 C24 C25 2.9(6) . . . . ?
C23 C24 C25 C20 -0.7(5) . . . . ?
C25 C20 C21 C22 2.0(4) . . . . ?
C26 P1 C10 C9 -77.5(2) . . . . ?
C26 P1 C10 C11 97.2(2) . . . . ?
C26 P1 C20 C21 -35.8(3) . . . . ?
C26 P1 C20 C25 145.2(2) . . . . ?
C26 C27 C28 C29 -0.7(6) . . . . ?
C27 C26 C31 C30 -0.2(5) . . . . ?
C27 C28 C29 C30 -0.5(7) . . . . ?
C28 C29 C30 C31 1.4(7) . . . . ?
C29 C30 C31 C26 -1.1(6) . . . . ?
C31 C26 C27 C28 1.0(5) . . . . ?
C32 N2 C9 C8 -13.1(4) . . . . ?
C32 N2 C9 C10 165.9(3) . . . . ?
C32 C33 C34 C35 -179.5(3) . . . . ?
C32 C33 C38 C37 179.2(4) . . . . ?
C33 C34 C35 C36 0.7(7) . . . . ?
C34 C33 C38 C37 0.2(6) . . . . ?
C34 C35 C36 C37 -0.5(9) . . . . ?
C35 C36 C37 C38 0.2(9) . . . . ?
C36 C37 C38 C33 -0.1(8) . . . . ?
C38 C33 C34 C35 -0.5(6) . . . . ?
C40 C3 C4 C5 -176.2(3) . . . . ?
