#------------------------------------------------------------------------------
#$Date: 2024-06-28 12:32:51 +0300 (Fri, 28 Jun 2024) $
#$Revision: 292638 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/63/7126337.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_7126337
loop_
_publ_author_name
'An, Yang'
'Zhang, Bo-Sheng'
'Zhang, Zhe'
'Liu, Ce'
'Gou, Xue-Ya'
'Ding, Ya-Nan'
'Liang, Yong-Min'
_publ_section_title
;
 A carboxylate-assisted amination/unactivated C(sp²)-H
 arylation reaction via a palladium/norbornene cooperative catalysis.
;
_journal_issue                   44
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              5933
_journal_page_last               5936
_journal_paper_doi               10.1039/c9cc09265j
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C20 H22 N2 O2'
_chemical_formula_sum            'C20 H22 N2 O2'
_chemical_formula_weight         322.39
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-07-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-10-09 deposited with the CCDC.	2020-04-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.1425(17)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.7868(3)
_cell_length_b                   9.84896(13)
_cell_length_c                   19.3586(3)
_cell_measurement_reflns_used    10414
_cell_measurement_temperature    292.39(14)
_cell_measurement_theta_max      69.7460
_cell_measurement_theta_min      6.4520
_cell_volume                     3403.85(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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 (Sheldrick, 2008)'
_diffrn_ambient_temperature      292.39(14)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -60.00   -1.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -63.0000   90.0000 59

#__ type_ start__ end____ width___ exp.time_
  2 omega  -39.00   -3.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  125.0000 -150.0000 36

#__ type_ start__ end____ width___ exp.time_
  3 omega  -70.00   15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -50.0000 -150.0000 85

#__ type_ start__ end____ width___ exp.time_
  4 omega  -86.00  -44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000  -30.0000 42

#__ type_ start__ end____ width___ exp.time_
  5 omega   32.00  123.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000   60.0000 91

#__ type_ start__ end____ width___ exp.time_
  6 omega   39.00  127.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   38.0000  -90.0000 88

#__ type_ start__ end____ width___ exp.time_
  7 omega    1.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -99.0000  120.0000 92

#__ type_ start__ end____ width___ exp.time_
  8 omega  -13.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  -90.0000 85

#__ type_ start__ end____ width___ exp.time_
  9 omega  125.00  175.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  120.0000 50

#__ type_ start__ end____ width___ exp.time_
 10 omega   34.00  108.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000   90.0000 74

#__ type_ start__ end____ width___ exp.time_
 11 omega   72.00  137.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000 -180.0000 65

#__ type_ start__ end____ width___ exp.time_
 12 omega   36.00   93.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -60.0000 57

#__ type_ start__ end____ width___ exp.time_
 13 omega   78.00  104.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 14 omega   38.00   77.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -150.0000 39

#__ type_ start__ end____ width___ exp.time_
 15 omega  101.00  145.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -165.0000  120.0000 44

#__ type_ start__ end____ width___ exp.time_
 16 omega   74.00  114.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 40

#__ type_ start__ end____ width___ exp.time_
 17 omega   34.00   60.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 18 omega   79.00  146.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000 -150.0000 67

#__ type_ start__ end____ width___ exp.time_
 19 omega   36.00  146.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000   60.0000 110

#__ type_ start__ end____ width___ exp.time_
 20 omega   67.00  104.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -150.0000 37

#__ type_ start__ end____ width___ exp.time_
 21 omega   35.00  112.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 77

#__ type_ start__ end____ width___ exp.time_
 22 omega   35.00   93.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   60.0000 58

#__ type_ start__ end____ width___ exp.time_
 23 omega   79.00  104.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 24 omega   45.00   72.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
 25 omega   45.00  103.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000    0.0000 58

#__ type_ start__ end____ width___ exp.time_
 26 omega   44.00   70.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 27 omega   58.00   94.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  120.0000 36

#__ type_ start__ end____ width___ exp.time_
 28 omega   49.00   89.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -120.0000 40

#__ type_ start__ end____ width___ exp.time_
 29 omega   47.00   77.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -120.0000 30

#__ type_ start__ end____ width___ exp.time_
 30 omega   70.00  173.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000   90.0000 103

#__ type_ start__ end____ width___ exp.time_
 31 omega   75.00  100.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -165.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 32 omega   99.00  125.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 33 omega   60.00  111.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000   60.0000 51
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0217927000
_diffrn_orient_matrix_UB_12      0.1032965000
_diffrn_orient_matrix_UB_13      -0.0628859000
_diffrn_orient_matrix_UB_21      -0.0020056000
_diffrn_orient_matrix_UB_22      -0.1150555000
_diffrn_orient_matrix_UB_23      -0.0544967000
_diffrn_orient_matrix_UB_31      -0.0834460000
_diffrn_orient_matrix_UB_32      -0.0241850000
_diffrn_orient_matrix_UB_33      -0.0092197000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            24742
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        66.590
_diffrn_reflns_theta_max         66.590
_diffrn_reflns_theta_min         4.672
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_description       block
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         5971
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0384
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0529P)²+0.6645P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.1040
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5298
_reflns_number_total             5971
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc09265j2.cif
_cod_data_source_block           any211_0711
_cod_depositor_comments
;
Adding full bibliography for 7126337--7126341.cif.

2024-06-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C40 H44 N4 O4'
_cod_original_formula_weight         644.79
_cod_original_formula_moiety         '2(C20 H22 N2 O2)'
_cod_original_formula_units_Z            4
_cod_original_cell_volume        3403.86(9)
_cod_database_code               7126337
_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.
;
_reflns_odcompleteness_completeness 99.15
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C30(H30A,H30B), C32(H32A,H32B), C33(H33A,H33B), C37(H37A,H37B),
 C38(H38A,H38B), C39(H39A,H39B), C40(H40A,H40B), C42(H42A,H42B), C44(H44A,H44B),
  C46(H46A,H46B), C47(H47A,H47B)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C18(H18), C19(H19), C23(H23), C25(H25), C26(H26), C27(H27),
 C28(H28), C29(H29), C34(H34), C35(H35), C36(H36), C41(H41), C45(H45)
2.c Idealised Me refined as rotating group:
 C43(H43A,H43B,H43C), C48(H48A,H48B,H48C)
;
_olex2_date_sample_data_collection 2019-07-11
_olex2_submission_special_instructions 'No special instructions were received'
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
O1 O 0.40181(6) 0.07544(10) 0.32946(6) 0.0545(3) Uani 1 1 d . . . . .
C2 C 0.36198(6) 0.41929(12) 0.23272(6) 0.0317(2) Uani 1 1 d . . . . .
N3 N 0.35529(6) 0.57682(11) 0.13305(5) 0.0373(2) Uani 1 1 d . . . . .
O4 O 0.40094(7) 0.16149(12) 0.43676(6) 0.0610(3) Uani 1 1 d . . . . .
N5 N 0.35194(6) 0.28055(11) 0.33212(6) 0.0403(2) Uani 1 1 d . . . . .
N6 N 0.14981(6) -0.01273(11) 0.35360(6) 0.0383(2) Uani 1 1 d . . . . .
C7 C 0.33751(6) 0.29776(12) 0.25575(7) 0.0353(3) Uani 1 1 d . . . . .
C8 C 0.41376(6) 0.50564(12) 0.28934(6) 0.0332(2) Uani 1 1 d . . . . .
C9 C 0.34911(8) 0.40760(14) 0.37073(7) 0.0447(3) Uani 1 1 d . . . . .
H9A H 0.359175 0.389949 0.422187 0.054 Uiso 1 1 calc R . . . .
H9B H 0.299810 0.448313 0.351993 0.054 Uiso 1 1 calc R . . . .
C10 C -0.00410(7) 0.06187(13) 0.35126(7) 0.0386(3) Uani 1 1 d . . . . .
N11 N -0.01643(7) 0.28449(12) 0.43229(7) 0.0513(3) Uani 1 1 d . . . . .
O12 O -0.02498(7) 0.49526(11) 0.38741(7) 0.0642(3) Uani 1 1 d . . . . .
C13 C 0.06391(7) 0.14415(13) 0.38618(6) 0.0352(3) Uani 1 1 d . . . . .
C14 C 0.33840(6) 0.44873(13) 0.15720(6) 0.0339(3) Uani 1 1 d . . . . .
C15 C 0.47198(7) 0.58116(13) 0.27809(7) 0.0393(3) Uani 1 1 d . . . . .
H15 H 0.478018 0.583197 0.232209 0.047 Uiso 1 1 calc R . . . .
C16 C 0.05477(8) 0.26400(14) 0.42178(7) 0.0418(3) Uani 1 1 d . . . . .
O17 O -0.12259(7) 0.40792(13) 0.41656(7) 0.0697(3) Uani 1 1 d . . . . .
C18 C 0.27978(7) 0.22699(14) 0.13354(8) 0.0456(3) Uani 1 1 d . . . . .
H18 H 0.254984 0.161298 0.100210 0.055 Uiso 1 1 calc R . . . .
C19 C 0.19394(7) 0.20744(14) 0.40946(7) 0.0427(3) Uani 1 1 d . . . . .
H19 H 0.241395 0.188934 0.406352 0.051 Uiso 1 1 calc R . . . .
C20 C 0.40717(7) 0.50151(12) 0.35933(7) 0.0374(3) Uani 1 1 d . . . . .
C21 C 0.13661(7) 0.11243(13) 0.38335(6) 0.0350(3) Uani 1 1 d . . . . .
C22 C 0.38687(7) 0.17125(14) 0.37177(7) 0.0423(3) Uani 1 1 d . . . . .
C23 C 0.29724(7) 0.20126(13) 0.20658(7) 0.0418(3) Uani 1 1 d . . . . .
H23 H 0.282384 0.120561 0.222935 0.050 Uiso 1 1 calc R . . . .
C24 C -0.06237(8) 0.06639(14) 0.38216(9) 0.0493(3) Uani 1 1 d . . . . .
C25 C 0.45565(8) 0.57617(14) 0.41518(7) 0.0457(3) Uani 1 1 d . . . . .
H25 H 0.449981 0.574927 0.461218 0.055 Uiso 1 1 calc R . . . .
C26 C 0.29864(7) 0.34963(14) 0.10885(7) 0.0421(3) Uani 1 1 d . . . . .
H26 H 0.284575 0.366312 0.059125 0.051 Uiso 1 1 calc R . . . .
C27 C -0.01498(7) -0.01210(14) 0.28738(7) 0.0444(3) Uani 1 1 d . . . . .
H27 H 0.022184 -0.012540 0.264956 0.053 Uiso 1 1 calc R . . . .
C28 C 0.18126(8) 0.32880(15) 0.43990(8) 0.0486(3) Uani 1 1 d . . . . .
H28 H 0.219625 0.392317 0.454896 0.058 Uiso 1 1 calc R . . . .
C29 C 0.11268(9) 0.35649(14) 0.44821(8) 0.0491(3) Uani 1 1 d . . . . .
H29 H 0.105198 0.435751 0.471135 0.059 Uiso 1 1 calc R . . . .
C30 C 0.34764(9) 0.58801(16) 0.05594(7) 0.0505(3) Uani 1 1 d . . . . .
H30A H 0.295041 0.584489 0.027605 0.061 Uiso 1 1 calc R . . . .
H30B H 0.372742 0.512135 0.041520 0.061 Uiso 1 1 calc R . . . .
C31 C -0.06007(9) 0.39777(15) 0.41215(8) 0.0508(3) Uani 1 1 d . . . . .
C32 C 0.13783(8) -0.13380(14) 0.39307(8) 0.0465(3) Uani 1 1 d . . . . .
H32A H 0.090828 -0.124933 0.403602 0.056 Uiso 1 1 calc R . . . .
H32B H 0.177774 -0.140757 0.438924 0.056 Uiso 1 1 calc R . . . .
C33 C 0.31898(9) 0.69143(14) 0.15741(8) 0.0488(3) Uani 1 1 d . . . . .
H33A H 0.324872 0.681256 0.208731 0.059 Uiso 1 1 calc R . . . .
H33B H 0.265813 0.691073 0.131014 0.059 Uiso 1 1 calc R . . . .
C34 C 0.51231(8) 0.65236(15) 0.40286(8) 0.0513(4) Uani 1 1 d . . . . .
H34 H 0.544467 0.702808 0.440323 0.062 Uiso 1 1 calc R . . . .
C35 C 0.52080(7) 0.65302(15) 0.33449(8) 0.0477(3) Uani 1 1 d . . . . .
H35 H 0.559680 0.702211 0.326355 0.057 Uiso 1 1 calc R . . . .
C36 C -0.08017(8) -0.08477(16) 0.25690(10) 0.0589(4) Uani 1 1 d . . . . .
H36 H -0.086497 -0.133558 0.214269 0.071 Uiso 1 1 calc R . . . .
C37 C 0.21937(8) -0.02244(16) 0.33548(9) 0.0515(3) Uani 1 1 d . . . . .
H37A H 0.261369 -0.027867 0.379838 0.062 Uiso 1 1 calc R . . . .
H37B H 0.225568 0.058469 0.309360 0.062 Uiso 1 1 calc R . . . .
C38 C -0.05165(10) 0.15916(16) 0.44596(10) 0.0607(4) Uani 1 1 d . . . . .
H38A H -0.099655 0.179395 0.452549 0.073 Uiso 1 1 calc R . . . .
H38B H -0.020101 0.115838 0.489819 0.073 Uiso 1 1 calc R . . . .
C39 C 0.38132(12) 0.71984(19) 0.04070(9) 0.0688(5) Uani 1 1 d . . . . .
H39A H 0.434809 0.719309 0.065644 0.083 Uiso 1 1 calc R . . . .
H39B H 0.373909 0.727007 -0.011045 0.083 Uiso 1 1 calc R . . . .
C40 C 0.35269(12) 0.82526(16) 0.14499(10) 0.0675(5) Uani 1 1 d . . . . .
H40A H 0.404931 0.828788 0.174438 0.081 Uiso 1 1 calc R . . . .
H40B H 0.326657 0.899414 0.159727 0.081 Uiso 1 1 calc R . . . .
C41 C -0.12727(8) -0.00908(17) 0.35118(12) 0.0670(5) Uani 1 1 d . . . . .
H41 H -0.165319 -0.008042 0.372485 0.080 Uiso 1 1 calc R . . . .
C42 C 0.13611(10) -0.26139(17) 0.34884(11) 0.0677(5) Uani 1 1 d . . . . .
H42A H 0.092814 -0.258907 0.305511 0.081 Uiso 1 1 calc R . . . .
H42B H 0.131345 -0.340092 0.377204 0.081 Uiso 1 1 calc R . . . .
C43 C 0.43660(10) -0.04606(17) 0.36551(11) 0.0687(5) Uani 1 1 d . . . . .
H43A H 0.445464 -0.107312 0.330486 0.103 Uiso 1 1 calc GR . . . .
H43B H 0.404226 -0.088594 0.388882 0.103 Uiso 1 1 calc GR . . . .
H43C H 0.483372 -0.023495 0.401248 0.103 Uiso 1 1 calc GR . . . .
C44 C 0.34666(13) 0.84142(18) 0.06518(10) 0.0739(5) Uani 1 1 d . . . . .
H44A H 0.294430 0.849199 0.036159 0.089 Uiso 1 1 calc R . . . .
H44B H 0.372352 0.923463 0.058561 0.089 Uiso 1 1 calc R . . . .
C45 C -0.13578(9) -0.08526(18) 0.28936(12) 0.0711(5) Uani 1 1 d . . . . .
H45 H -0.178872 -0.136697 0.269701 0.085 Uiso 1 1 calc R . . . .
C46 C 0.20686(11) -0.27445(19) 0.32704(12) 0.0773(6) Uani 1 1 d . . . . .
H46A H 0.249560 -0.289764 0.369932 0.093 Uiso 1 1 calc R . . . .
H46B H 0.202388 -0.351547 0.294781 0.093 Uiso 1 1 calc R . . . .
C47 C 0.21881(11) -0.1464(2) 0.28915(11) 0.0709(5) Uani 1 1 d . . . . .
H47A H 0.179151 -0.137563 0.243221 0.085 Uiso 1 1 calc R . . . .
H47B H 0.266091 -0.152414 0.278934 0.085 Uiso 1 1 calc R . . . .
C48 C -0.06572(11) 0.61970(18) 0.36642(12) 0.0743(5) Uani 1 1 d . . . . .
H48A H -0.109699 0.603093 0.325878 0.111 Uiso 1 1 calc GR . . . .
H48B H -0.034565 0.685052 0.352842 0.111 Uiso 1 1 calc GR . . . .
H48C H -0.080133 0.654207 0.406493 0.111 Uiso 1 1 calc GR . . . .
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'
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
C22 O1 C43 116.21(12) . . ?
C7 C2 C8 117.24(10) . . ?
C7 C2 C14 118.25(11) . . ?
C14 C2 C8 124.45(11) . . ?
C14 N3 C30 116.40(10) . . ?
C14 N3 C33 113.84(10) . . ?
C30 N3 C33 111.25(11) . . ?
C7 N5 C9 113.64(10) . . ?
C22 N5 C7 125.36(11) . . ?
C22 N5 C9 118.25(11) . . ?
C21 N6 C32 114.85(10) . . ?
C21 N6 C37 116.04(10) . . ?
C37 N6 C32 111.43(11) . . ?
C2 C7 N5 117.05(11) . . ?
C23 C7 C2 121.84(11) . . ?
C23 C7 N5 121.01(11) . . ?
C15 C8 C2 123.73(11) . . ?
C15 C8 C20 118.48(11) . . ?
C20 C8 C2 117.57(11) . . ?
N5 C9 H9A 110.1 . . ?
N5 C9 H9B 110.1 . . ?
N5 C9 C20 107.94(10) . . ?
H9A C9 H9B 108.4 . . ?
C20 C9 H9A 110.1 . . ?
C20 C9 H9B 110.1 . . ?
C24 C10 C13 117.61(12) . . ?
C27 C10 C13 123.79(11) . . ?
C27 C10 C24 118.47(13) . . ?
C16 N11 C38 113.76(11) . . ?
C31 N11 C16 125.42(12) . . ?
C31 N11 C38 118.36(13) . . ?
C31 O12 C48 115.87(13) . . ?
C16 C13 C10 117.54(11) . . ?
C16 C13 C21 118.06(11) . . ?
C21 C13 C10 124.34(11) . . ?
N3 C14 C2 119.48(10) . . ?
C26 C14 C2 118.54(11) . . ?
C26 C14 N3 121.98(11) . . ?
C8 C15 H15 119.7 . . ?
C35 C15 C8 120.62(12) . . ?
C35 C15 H15 119.7 . . ?
C13 C16 N11 116.86(12) . . ?
C29 C16 N11 121.04(12) . . ?
C29 C16 C13 122.06(12) . . ?
C23 C18 H18 119.6 . . ?
C23 C18 C26 120.80(12) . . ?
C26 C18 H18 119.6 . . ?
C21 C19 H19 119.5 . . ?
C28 C19 H19 119.5 . . ?
C28 C19 C21 121.08(12) . . ?
C8 C20 C9 116.67(11) . . ?
C25 C20 C8 120.30(12) . . ?
C25 C20 C9 122.93(12) . . ?
N6 C21 C13 120.03(11) . . ?
C19 C21 N6 121.18(11) . . ?
C19 C21 C13 118.79(12) . . ?
O1 C22 N5 111.61(11) . . ?
O4 C22 O1 124.32(13) . . ?
O4 C22 N5 124.06(13) . . ?
C7 C23 H23 120.5 . . ?
C18 C23 C7 118.94(12) . . ?
C18 C23 H23 120.5 . . ?
C10 C24 C38 116.65(13) . . ?
C41 C24 C10 119.60(16) . . ?
C41 C24 C38 123.69(14) . . ?
C20 C25 H25 119.8 . . ?
C34 C25 C20 120.47(12) . . ?
C34 C25 H25 119.8 . . ?
C14 C26 H26 119.4 . . ?
C18 C26 C14 121.25(12) . . ?
C18 C26 H26 119.4 . . ?
C10 C27 H27 119.5 . . ?
C36 C27 C10 121.00(14) . . ?
C36 C27 H27 119.5 . . ?
C19 C28 H28 119.6 . . ?
C29 C28 C19 120.84(13) . . ?
C29 C28 H28 119.6 . . ?
C16 C29 H29 120.6 . . ?
C28 C29 C16 118.82(13) . . ?
C28 C29 H29 120.6 . . ?
N3 C30 H30A 109.5 . . ?
N3 C30 H30B 109.5 . . ?
N3 C30 C39 110.52(12) . . ?
H30A C30 H30B 108.1 . . ?
C39 C30 H30A 109.5 . . ?
C39 C30 H30B 109.5 . . ?
O12 C31 N11 111.70(13) . . ?
O17 C31 N11 123.87(15) . . ?
O17 C31 O12 124.43(14) . . ?
N6 C32 H32A 109.4 . . ?
N6 C32 H32B 109.4 . . ?
N6 C32 C42 111.01(13) . . ?
H32A C32 H32B 108.0 . . ?
C42 C32 H32A 109.4 . . ?
C42 C32 H32B 109.4 . . ?
N3 C33 H33A 109.4 . . ?
N3 C33 H33B 109.4 . . ?
N3 C33 C40 111.02(12) . . ?
H33A C33 H33B 108.0 . . ?
C40 C33 H33A 109.4 . . ?
C40 C33 H33B 109.4 . . ?
C25 C34 H34 120.2 . . ?
C35 C34 C25 119.51(12) . . ?
C35 C34 H34 120.2 . . ?
C15 C35 H35 119.7 . . ?
C34 C35 C15 120.55(13) . . ?
C34 C35 H35 119.7 . . ?
C27 C36 H36 119.9 . . ?
C45 C36 C27 120.29(17) . . ?
C45 C36 H36 119.9 . . ?
N6 C37 H37A 109.5 . . ?
N6 C37 H37B 109.5 . . ?
N6 C37 C47 110.75(13) . . ?
H37A C37 H37B 108.1 . . ?
C47 C37 H37A 109.5 . . ?
C47 C37 H37B 109.5 . . ?
N11 C38 C24 108.52(12) . . ?
N11 C38 H38A 110.0 . . ?
N11 C38 H38B 110.0 . . ?
C24 C38 H38A 110.0 . . ?
C24 C38 H38B 110.0 . . ?
H38A C38 H38B 108.4 . . ?
C30 C39 H39A 109.2 . . ?
C30 C39 H39B 109.2 . . ?
H39A C39 H39B 107.9 . . ?
C44 C39 C30 111.86(14) . . ?
C44 C39 H39A 109.2 . . ?
C44 C39 H39B 109.2 . . ?
C33 C40 H40A 109.6 . . ?
C33 C40 H40B 109.6 . . ?
C33 C40 C44 110.47(14) . . ?
H40A C40 H40B 108.1 . . ?
C44 C40 H40A 109.6 . . ?
C44 C40 H40B 109.6 . . ?
C24 C41 H41 119.6 . . ?
C45 C41 C24 120.87(15) . . ?
C45 C41 H41 119.6 . . ?
C32 C42 H42A 109.4 . . ?
C32 C42 H42B 109.4 . . ?
C32 C42 C46 111.13(14) . . ?
H42A C42 H42B 108.0 . . ?
C46 C42 H42A 109.4 . . ?
C46 C42 H42B 109.4 . . ?
O1 C43 H43A 109.5 . . ?
O1 C43 H43B 109.5 . . ?
O1 C43 H43C 109.5 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C39 C44 C40 109.45(15) . . ?
C39 C44 H44A 109.8 . . ?
C39 C44 H44B 109.8 . . ?
C40 C44 H44A 109.8 . . ?
C40 C44 H44B 109.8 . . ?
H44A C44 H44B 108.2 . . ?
C36 C45 C41 119.66(15) . . ?
C36 C45 H45 120.2 . . ?
C41 C45 H45 120.2 . . ?
C42 C46 H46A 109.7 . . ?
C42 C46 H46B 109.7 . . ?
H46A C46 H46B 108.2 . . ?
C47 C46 C42 109.83(14) . . ?
C47 C46 H46A 109.7 . . ?
C47 C46 H46B 109.7 . . ?
C37 C47 H47A 109.4 . . ?
C37 C47 H47B 109.4 . . ?
C46 C47 C37 111.13(15) . . ?
C46 C47 H47A 109.4 . . ?
C46 C47 H47B 109.4 . . ?
H47A C47 H47B 108.0 . . ?
O12 C48 H48A 109.5 . . ?
O12 C48 H48B 109.5 . . ?
O12 C48 H48C 109.5 . . ?
H48A C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 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
O1 C22 1.3354(17) . ?
O1 C43 1.4360(18) . ?
C2 C7 1.4038(17) . ?
C2 C8 1.4856(16) . ?
C2 C14 1.4192(16) . ?
N3 C14 1.4153(16) . ?
N3 C30 1.4586(16) . ?
N3 C33 1.4705(17) . ?
O4 C22 1.2061(17) . ?
N5 C7 1.4277(16) . ?
N5 C9 1.4669(17) . ?
N5 C22 1.3657(17) . ?
N6 C21 1.4148(16) . ?
N6 C32 1.4709(17) . ?
N6 C37 1.4578(16) . ?
C7 C23 1.3904(18) . ?
C8 C15 1.3948(18) . ?
C8 C20 1.3991(17) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C20 1.4980(19) . ?
C10 C13 1.4860(17) . ?
C10 C24 1.4021(18) . ?
C10 C27 1.394(2) . ?
N11 C16 1.4285(17) . ?
N11 C31 1.3675(19) . ?
N11 C38 1.463(2) . ?
O12 C31 1.335(2) . ?
O12 C48 1.4350(19) . ?
C13 C16 1.4041(18) . ?
C13 C21 1.4187(17) . ?
C14 C26 1.3968(18) . ?
C15 H15 0.9300 . ?
C15 C35 1.3822(19) . ?
C16 C29 1.389(2) . ?
O17 C31 1.2078(19) . ?
C18 H18 0.9300 . ?
C18 C23 1.372(2) . ?
C18 C26 1.385(2) . ?
C19 H19 0.9300 . ?
C19 C21 1.3972(18) . ?
C19 C28 1.386(2) . ?
C20 C25 1.3878(19) . ?
C23 H23 0.9300 . ?
C24 C38 1.499(2) . ?
C24 C41 1.394(2) . ?
C25 H25 0.9300 . ?
C25 C34 1.382(2) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C27 C36 1.382(2) . ?
C28 H28 0.9300 . ?
C28 C29 1.374(2) . ?
C29 H29 0.9300 . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C30 C39 1.513(2) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C32 C42 1.515(2) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C33 C40 1.514(2) . ?
C34 H34 0.9300 . ?
C34 C35 1.382(2) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C36 C45 1.377(3) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C37 C47 1.513(2) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C39 C44 1.508(3) . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C40 C44 1.522(2) . ?
C41 H41 0.9300 . ?
C41 C45 1.379(3) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C42 C46 1.520(3) . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?
C44 H44A 0.9700 . ?
C44 H44B 0.9700 . ?
C45 H45 0.9300 . ?
C46 H46A 0.9700 . ?
C46 H46B 0.9700 . ?
C46 C47 1.510(3) . ?
C47 H47A 0.9700 . ?
C47 H47B 0.9700 . ?
C48 H48A 0.9600 . ?
C48 H48B 0.9600 . ?
C48 H48C 0.9600 . ?
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
C2 C7 C23 C18 -1.29(19) . . . . ?
C2 C8 C15 C35 -176.15(12) . . . . ?
C2 C8 C20 C9 1.18(16) . . . . ?
C2 C8 C20 C25 177.72(11) . . . . ?
C2 C14 C26 C18 2.49(18) . . . . ?
N3 C14 C26 C18 -177.20(12) . . . . ?
N3 C30 C39 C44 -56.68(19) . . . . ?
N3 C33 C40 C44 57.08(19) . . . . ?
N5 C7 C23 C18 175.03(12) . . . . ?
N5 C9 C20 C8 41.67(15) . . . . ?
N5 C9 C20 C25 -134.77(12) . . . . ?
N6 C32 C42 C46 55.49(18) . . . . ?
N6 C37 C47 C46 -57.41(19) . . . . ?
C7 C2 C8 C15 144.30(12) . . . . ?
C7 C2 C8 C20 -30.25(15) . . . . ?
C7 C2 C14 N3 173.11(10) . . . . ?
C7 C2 C14 C26 -6.59(16) . . . . ?
C7 N5 C9 C20 -59.89(14) . . . . ?
C7 N5 C22 O1 -4.45(18) . . . . ?
C7 N5 C22 O4 177.05(13) . . . . ?
C8 C2 C7 N5 12.23(15) . . . . ?
C8 C2 C7 C23 -171.31(11) . . . . ?
C8 C2 C14 N3 -9.65(17) . . . . ?
C8 C2 C14 C26 170.65(11) . . . . ?
C8 C15 C35 C34 -0.6(2) . . . . ?
C8 C20 C25 C34 -1.85(19) . . . . ?
C9 N5 C7 C2 33.49(15) . . . . ?
C9 N5 C7 C23 -142.99(12) . . . . ?
C9 N5 C22 O1 -164.41(11) . . . . ?
C9 N5 C22 O4 17.1(2) . . . . ?
C9 C20 C25 C34 174.47(12) . . . . ?
C10 C13 C16 N11 10.56(17) . . . . ?
C10 C13 C16 C29 -171.84(12) . . . . ?
C10 C13 C21 N6 -8.08(18) . . . . ?
C10 C13 C21 C19 171.07(12) . . . . ?
C10 C24 C38 N11 39.91(18) . . . . ?
C10 C24 C41 C45 -1.8(2) . . . . ?
C10 C27 C36 C45 0.0(2) . . . . ?
N11 C16 C29 C28 176.77(13) . . . . ?
C13 C10 C24 C38 2.58(18) . . . . ?
C13 C10 C24 C41 179.94(12) . . . . ?
C13 C10 C27 C36 -178.83(12) . . . . ?
C13 C16 C29 C28 -0.7(2) . . . . ?
C14 C2 C7 N5 -170.33(10) . . . . ?
C14 C2 C7 C23 6.13(17) . . . . ?
C14 C2 C8 C15 -32.96(18) . . . . ?
C14 C2 C8 C20 152.49(11) . . . . ?
C14 N3 C30 C39 -169.12(13) . . . . ?
C14 N3 C33 C40 166.91(12) . . . . ?
C15 C8 C20 C9 -173.66(11) . . . . ?
C15 C8 C20 C25 2.88(18) . . . . ?
C16 N11 C31 O12 -6.3(2) . . . . ?
C16 N11 C31 O17 173.94(15) . . . . ?
C16 N11 C38 C24 -59.53(17) . . . . ?
C16 C13 C21 N6 174.59(11) . . . . ?
C16 C13 C21 C19 -6.26(17) . . . . ?
C19 C28 C29 C16 -3.6(2) . . . . ?
C20 C8 C15 C35 -1.64(19) . . . . ?
C20 C25 C34 C35 -0.5(2) . . . . ?
C21 N6 C32 C42 167.29(12) . . . . ?
C21 N6 C37 C47 -167.14(13) . . . . ?
C21 C13 C16 N11 -171.93(11) . . . . ?
C21 C13 C16 C29 5.67(19) . . . . ?
C21 C19 C28 C29 2.9(2) . . . . ?
C22 N5 C7 C2 -127.27(13) . . . . ?
C22 N5 C7 C23 56.25(17) . . . . ?
C22 N5 C9 C20 102.35(13) . . . . ?
C23 C18 C26 C14 2.5(2) . . . . ?
C24 C10 C13 C16 -29.84(16) . . . . ?
C24 C10 C13 C21 152.82(12) . . . . ?
C24 C10 C27 C36 -3.0(2) . . . . ?
C24 C41 C45 C36 -1.3(2) . . . . ?
C25 C34 C35 C15 1.7(2) . . . . ?
C26 C18 C23 C7 -3.1(2) . . . . ?
C27 C10 C13 C16 145.98(13) . . . . ?
C27 C10 C13 C21 -31.36(19) . . . . ?
C27 C10 C24 C38 -173.46(13) . . . . ?
C27 C10 C24 C41 3.89(19) . . . . ?
C27 C36 C45 C41 2.2(2) . . . . ?
C28 C19 C21 N6 -178.70(12) . . . . ?
C28 C19 C21 C13 2.16(19) . . . . ?
C30 N3 C14 C2 164.26(11) . . . . ?
C30 N3 C14 C26 -16.05(17) . . . . ?
C30 N3 C33 C40 -59.19(16) . . . . ?
C30 C39 C44 C40 54.5(2) . . . . ?
C31 N11 C16 C13 -127.07(15) . . . . ?
C31 N11 C16 C29 55.3(2) . . . . ?
C31 N11 C38 C24 103.64(15) . . . . ?
C32 N6 C21 C13 -63.00(15) . . . . ?
C32 N6 C21 C19 117.87(13) . . . . ?
C32 N6 C37 C47 58.90(17) . . . . ?
C32 C42 C46 C47 -53.6(2) . . . . ?
C33 N3 C14 C2 -64.31(14) . . . . ?
C33 N3 C14 C26 115.38(13) . . . . ?
C33 N3 C30 C39 58.25(16) . . . . ?
C33 C40 C44 C39 -54.3(2) . . . . ?
C37 N6 C21 C13 164.59(12) . . . . ?
C37 N6 C21 C19 -14.54(17) . . . . ?
C37 N6 C32 C42 -58.16(15) . . . . ?
C38 N11 C16 C13 34.72(18) . . . . ?
C38 N11 C16 C29 -142.91(14) . . . . ?
C38 N11 C31 O12 -167.30(13) . . . . ?
C38 N11 C31 O17 12.9(2) . . . . ?
C38 C24 C41 C45 175.38(15) . . . . ?
C41 C24 C38 N11 -137.33(15) . . . . ?
C42 C46 C47 C37 54.5(2) . . . . ?
C43 O1 C22 O4 0.3(2) . . . . ?
C43 O1 C22 N5 -178.19(13) . . . . ?
C48 O12 C31 N11 -178.63(15) . . . . ?
C48 O12 C31 O17 1.2(2) . . . . ?
