#------------------------------------------------------------------------------
#$Date: 2024-04-17 04:38:50 +0300 (Wed, 17 Apr 2024) $
#$Revision: 291248 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/84/7248423.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_7248423
loop_
_publ_author_name
'Antoniou, Ioakeim M.'
'Ioannou, Natalia'
'Panagiotou, Nikos'
'Georgiades, Savvas N.'
_publ_section_title
;
 LED-induced Ru-photoredox Pd-catalyzed C--H arylation of
 (6-phenylpyridin-2-yl)pyrimidines and heteroaryl counterparts
;
_journal_issue                   17
_journal_name_full               'RSC Advances'
_journal_page_first              12179
_journal_page_last               12191
_journal_paper_doi               10.1039/D4RA02173H
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C42 H32 N4 O2, C4 H8 O2'
_chemical_formula_sum            'C46 H40 N4 O4'
_chemical_formula_weight         712.82
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-08-29
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-11-12 deposited with the CCDC.	2024-04-10 downloaded from the CCDC.
;
_cell_angle_alpha                102.097(2)
_cell_angle_beta                 99.993(2)
_cell_angle_gamma                106.014(2)
_cell_formula_units_Z            2
_cell_length_a                   10.1753(2)
_cell_length_b                   10.8280(2)
_cell_length_c                   18.8802(3)
_cell_measurement_reflns_used    12952
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.2940
_cell_measurement_theta_min      4.3860
_cell_volume                     1894.91(7)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      180.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -89.00 -58.00   0.50    0.50    --  -47.44-151.00-110.00   62
  2  ω    -51.00 -18.00   0.50    0.50    --  -47.44 123.00 131.00   66
  3  ω   -108.00 -68.00   0.50    0.50    --  -47.44 151.00 -66.00   80
  4  ω     57.00  82.00   0.50    0.50    --   47.44 151.00 -66.00   50
  5  ω     69.00 104.00   0.50    0.50    --   47.44-151.00-110.00   70
  6  ω     25.00  91.00   0.50    0.50    --   47.44-123.00  51.00  132
  7  ω    -95.00 -56.00   0.50    2.00    -- -106.00 123.00 131.00   78
  8  ω   -125.00 -58.00   0.50    2.00    -- -106.00 151.00 -66.00  134
  9  ω   -126.00 -77.00   0.50    2.00    -- -106.00-123.00  51.00   98
 10  ω     86.00 111.00   0.50    2.00    --  106.24 151.00 -66.00   50
 11  ω     68.00  93.00   0.50    2.00    --  106.24-123.00  51.00   50
 12  ω     65.00 130.00   0.50    2.00    --  106.24-151.00-110.00  130
 13  ω    101.00 138.00   0.50    2.00    --  106.24 123.00 131.00   74
 14  ω     73.00  98.00   0.50    0.50    --   47.44 126.00  30.00   50
 15  ω    -21.00  28.00   0.50    0.50    --   47.44 -19.00 150.00   98
 16  ω    -24.00  41.00   0.50    0.50    --   47.44 -38.00 -90.00  130
 17  ω    -14.00  29.00   0.50    0.50    --   47.44 -19.00 -60.00   86
 18  ω     73.00  98.00   0.50    0.50    --   47.44 126.00   0.00   50
 19  ω    -24.00  30.00   0.50    0.50    --   47.44 -19.00-150.00  108
 20  ω   -108.00 -74.00   0.50    2.00    -- -106.00 112.00-110.98   68
 21  ω    -70.00 -45.00   0.50    2.00    -- -106.00 112.00-110.98   50
 22  ω   -107.00 -57.00   0.50    2.00    -- -106.00 126.00  90.00  100
 23  ω   -174.00 -97.00   0.50    2.00    -- -106.00 -15.00 -60.00  154
 24  ω    -97.00 -34.00   0.50    2.00    -- -106.00  77.00 -30.00  126
 25  ω    -71.00 -34.00   0.50    2.00    -- -106.00  61.00 -90.00   74
 26  ω   -100.00 -59.00   0.50    2.00    -- -106.00  77.00 -90.00   82
 27  ω   -122.00 -86.00   0.50    2.00    -- -106.00 140.00  24.48   72
 28  ω   -101.00 -40.00   0.50    2.00    -- -106.00 126.00 -60.00  122
 29  ω    105.00 162.00   0.50    2.00    --  106.24  15.00 120.00  114
 30  ω     42.00  68.00   0.50    2.00    --  106.24 -61.00-120.00   52
 31  ω     35.00  89.00   0.50    2.00    --  106.24 -77.00  30.00  108
 32  ω     35.00  70.00   0.50    2.00    --  106.24 -61.00  90.00   70
 33  ω     37.00  63.00   0.50    2.00    --  106.24 -61.00 -90.00   52
 34  ω     38.00  69.00   0.50    2.00    --  106.24 -61.00-180.00   62
 35  ω     35.00  71.00   0.50    2.00    --  106.24 -61.00 120.00   72
 36  ω     35.00  69.00   0.50    2.00    --  106.24 -61.00  30.00   68
 37  ω    101.00 178.00   0.50    2.00    --  106.24  30.00-180.00  154
 38  ω     42.00  67.00   0.50    2.00    --  106.24 -95.00  60.00   50
 39  ω     35.00  60.00   0.50    2.00    --  106.24 -77.00-120.00   50
 40  ω     96.00 170.00   0.50    2.00    --  106.24  45.00-150.00  148
 41  ω     36.00  70.00   0.50    2.00    --  106.24 -61.00  60.00   68
 42  ω    102.00 160.00   0.50    2.00    --  106.24  45.00  60.00  116
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            22574
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.992
_diffrn_reflns_theta_max         66.992
_diffrn_reflns_theta_min         4.415
_exptl_absorpt_coefficient_mu    0.641
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99017
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.041
_exptl_crystal_size_mid          0.031
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     547
_refine_ls_number_reflns         6736
_refine_ls_number_restraints     146
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0375
_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)+(0.0530P)²+0.3423P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1042
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5909
_reflns_number_total             6736
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ra02173h2.cif
_cod_data_source_block           ima_4-ph
_cod_original_cell_volume        1894.91(6)
_cod_database_code               7248423
_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   0.984
_shelx_estimated_absorpt_t_min   0.974
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O2-C3
 1.32 with sigma of 0.02
 O2-C7
 1.46 with sigma of 0.02
 O3-C3
 1.22 with sigma of 0.02
 C1-C3
 1.49 with sigma of 0.02
 C7-C11
 1.5 with sigma of 0.02
 O1-C1A
 1.32 with sigma of 0.02
 O1-C1B
 1.46 with sigma of 0.02
 O4-C1A
 1.22 with sigma of 0.02
 C12-C1A
 1.49 with sigma of 0.02
 C1B-C1C
 1.5 with sigma of 0.02
 O2-O3
 2.24 with sigma of 0.04
 O2-C1
 2.35 with sigma of 0.04
 O2-C11
 2.38 with sigma of 0.04
 O3-C1
 2.4 with sigma of 0.04
 O1-O4
 2.24 with sigma of 0.04
 O1-C12
 2.35 with sigma of 0.04
 O1-C1C
 2.38 with sigma of 0.04
 O4-C12
 2.4 with sigma of 0.04
 C1-C3 \\sim C7-C11
 with sigma of 0.02
 C12-C1A \\sim C1B-C1C
 with sigma of 0.02
3. Restrained planarity
 O2, O3, C1, C3, C7, C11
 with sigma of 0.1
 O1, O4, C1A, C1B, C1C, C12
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
O2 \\sim O3 \\sim C1 \\sim C3 \\sim C7 \\sim C11: within 2A with sigma of 0.04
and sigma for terminal atoms of 0.08 within 2A
O1 \\sim O4 \\sim C1A \\sim C1B \\sim C1C \\sim C12: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
5. Rigid body (RIGU) restrains
 O2, O3, C1, C3, C7, C11
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O1, O4, C1A, C1B, C1C, C12
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: O2(0.5) O3(0.5) C1(0.5) H1A(0.5) H1B(0.5) H1C(0.5) C3(0.5) C7(0.5)
 H7A(0.5) H7B(0.5) C11(0.5) H11A(0.5) H11B(0.5) H11C(0.5) O1(0.5) O4(0.5)
 C1A(0.5) C1B(0.5) H1BA(0.5) H1BB(0.5) C1C(0.5) H1CA(0.5) H1CB(0.5) H1CC(0.5)
 C12(0.5) H12A(0.5) H12B(0.5) H12C(0.5)
7.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C1B(H1BA,H1BB)
7.b Aromatic/amide H refined with riding coordinates:
 N12(H12), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C22(H22),
 C23(H23), C24(H24), C27(H27), C29(H29), C32(H32), C33(H33), C34(H34), C35(H35),
  C36(H36), C38(H38), C39(H39), C40(H40), C41(H41), C42(H42), C44(H44),
 C45(H45), C46(H46), C47(H47), C48(H48)
7.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C1(H1A,H1B,H1C), C11(H11A,H11B,H11C),
 C1C(H1CA,H1CB,H1CC), C12(H12A,H12B,H12C)
;
_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
;
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
O7 O -0.28135(10) 0.14918(10) 0.48804(5) 0.0427(2) Uani 1 1 d . . . . .
O11 O 0.36013(10) 0.35491(10) 0.62405(6) 0.0479(3) Uani 1 1 d . . . . .
N1 N -0.07190(11) 0.13658(10) 0.47419(6) 0.0346(2) Uani 1 1 d . . . . .
N3 N -0.09900(11) 0.24001(10) 0.59326(6) 0.0334(2) Uani 1 1 d . . . . .
N12 N 0.31496(11) 0.13904(10) 0.63019(6) 0.0340(2) Uani 1 1 d . . . . .
H12 H 0.249223 0.060193 0.613843 0.041 Uiso 1 1 calc R U . . .
N20 N 0.19724(11) 0.30499(9) 0.74265(5) 0.0305(2) Uani 1 1 d . . . . .
C2 C -0.14526(14) 0.17746(12) 0.52113(7) 0.0333(3) Uani 1 1 d . . . . .
C4 C 0.03620(13) 0.25704(11) 0.62400(7) 0.0312(3) Uani 1 1 d . . . . .
C5 C 0.12301(13) 0.21380(12) 0.58171(7) 0.0316(3) Uani 1 1 d . . . . .
C6 C 0.06450(14) 0.15842(12) 0.50476(7) 0.0325(3) Uani 1 1 d . . . . .
C8 C -0.37143(16) 0.18275(17) 0.53472(9) 0.0513(4) Uani 1 1 d . . . . .
H8A H -0.468740 0.153196 0.504546 0.077 Uiso 1 1 calc R U . . .
H8B H -0.339595 0.279642 0.556524 0.077 Uiso 1 1 calc R U . . .
H8C H -0.367170 0.138217 0.574808 0.077 Uiso 1 1 calc R U . . .
C9 C 0.15020(15) 0.12492(14) 0.45105(7) 0.0410(3) Uani 1 1 d . . . . .
H9A H 0.094226 0.041970 0.412520 0.061 Uiso 1 1 calc R U . . .
H9B H 0.235417 0.113349 0.478029 0.061 Uiso 1 1 calc R U . . .
H9C H 0.176965 0.197525 0.427505 0.061 Uiso 1 1 calc R U . . .
C10 C 0.27816(13) 0.24360(12) 0.61487(7) 0.0339(3) Uani 1 1 d . . . . .
C13 C 0.44882(13) 0.14434(13) 0.66992(7) 0.0353(3) Uani 1 1 d . . . . .
C14 C 0.47638(15) 0.02465(14) 0.66768(7) 0.0403(3) Uani 1 1 d . . . . .
H14 H 0.405692 -0.057875 0.640742 0.048 Uiso 1 1 calc R U . . .
C15 C 0.60715(17) 0.02626(17) 0.70485(9) 0.0499(4) Uani 1 1 d . . . . .
H15 H 0.626097 -0.055461 0.702460 0.060 Uiso 1 1 calc R U . . .
C16 C 0.71024(16) 0.14524(18) 0.74532(9) 0.0529(4) Uani 1 1 d . . . . .
H16 H 0.800205 0.145919 0.770049 0.063 Uiso 1 1 calc R U . . .
C17 C 0.68075(16) 0.26295(17) 0.74931(8) 0.0493(4) Uani 1 1 d . . . . .
H17 H 0.750453 0.344901 0.778084 0.059 Uiso 1 1 calc R U . . .
C18 C 0.55132(14) 0.26389(15) 0.71212(8) 0.0423(3) Uani 1 1 d . . . . .
H18 H 0.532637 0.345897 0.715426 0.051 Uiso 1 1 calc R U . . .
C19 C 0.08698(13) 0.32881(12) 0.70496(7) 0.0318(3) Uani 1 1 d . . . . .
C21 C 0.25036(13) 0.37061(11) 0.81508(7) 0.0306(3) Uani 1 1 d . . . . .
C22 C 0.19475(14) 0.46243(12) 0.85175(7) 0.0366(3) Uani 1 1 d . . . . .
H22 H 0.234958 0.508443 0.903090 0.044 Uiso 1 1 calc R U . . .
C23 C 0.08060(15) 0.48543(13) 0.81241(8) 0.0415(3) Uani 1 1 d . . . . .
H23 H 0.041029 0.547442 0.836355 0.050 Uiso 1 1 calc R U . . .
C24 C 0.02426(15) 0.41713(13) 0.73761(8) 0.0395(3) Uani 1 1 d . . . . .
H24 H -0.055105 0.430335 0.709404 0.047 Uiso 1 1 calc R U . . .
C25 C 0.37395(13) 0.34148(11) 0.85359(6) 0.0304(3) Uani 1 1 d . . . . .
C26 C 0.36140(13) 0.21103(11) 0.85935(6) 0.0301(3) Uani 1 1 d . . . . .
C27 C 0.47819(13) 0.18466(12) 0.89471(7) 0.0315(3) Uani 1 1 d . . . . .
H27 H 0.469334 0.096358 0.897721 0.038 Uiso 1 1 calc R U . . .
C28 C 0.60815(13) 0.28511(12) 0.92589(7) 0.0319(3) Uani 1 1 d . . . . .
C29 C 0.61888(13) 0.41269(12) 0.91904(7) 0.0330(3) Uani 1 1 d . . . . .
H29 H 0.707052 0.481754 0.939752 0.040 Uiso 1 1 calc R U . . .
C30 C 0.50541(13) 0.44297(12) 0.88300(6) 0.0312(3) Uani 1 1 d . . . . .
C31 C 0.22260(13) 0.10172(12) 0.83111(7) 0.0331(3) Uani 1 1 d . . . . .
C32 C 0.10870(15) 0.11392(14) 0.86016(9) 0.0433(3) Uani 1 1 d . . . . .
H32 H 0.119809 0.193244 0.896976 0.052 Uiso 1 1 calc R U . . .
C33 C -0.02012(16) 0.01343(16) 0.83675(11) 0.0561(4) Uani 1 1 d . . . . .
H33 H -0.095913 0.023113 0.858073 0.067 Uiso 1 1 calc R U . . .
C34 C -0.03800(18) -0.09992(19) 0.78280(11) 0.0666(5) Uani 1 1 d . . . . .
H34 H -0.126990 -0.168490 0.765769 0.080 Uiso 1 1 calc R U . . .
C35 C 0.0729(2) -0.11490(17) 0.75305(10) 0.0683(5) Uani 1 1 d . . . . .
H35 H 0.059926 -0.193877 0.715495 0.082 Uiso 1 1 calc R U . . .
C36 C 0.20459(18) -0.01468(14) 0.77774(8) 0.0488(4) Uani 1 1 d . . . . .
H36 H 0.281299 -0.026550 0.757912 0.059 Uiso 1 1 calc R U . . .
C37 C 0.53119(13) 0.58156(12) 0.87504(7) 0.0327(3) Uani 1 1 d . . . . .
C38 C 0.60452(14) 0.68969(12) 0.93704(7) 0.0364(3) Uani 1 1 d . . . . .
H38 H 0.631932 0.674449 0.984315 0.044 Uiso 1 1 calc R U . . .
C39 C 0.63801(15) 0.81911(13) 0.93068(8) 0.0435(3) Uani 1 1 d . . . . .
H39 H 0.688888 0.891807 0.973407 0.052 Uiso 1 1 calc R U . . .
C40 C 0.59780(16) 0.84304(13) 0.86248(9) 0.0467(3) Uani 1 1 d . . . . .
H40 H 0.620448 0.931921 0.858202 0.056 Uiso 1 1 calc R U . . .
C41 C 0.52435(17) 0.73670(14) 0.80052(9) 0.0487(4) Uani 1 1 d . . . . .
H41 H 0.496331 0.752764 0.753543 0.058 Uiso 1 1 calc R U . . .
C42 C 0.49119(15) 0.60661(13) 0.80639(8) 0.0417(3) Uani 1 1 d . . . . .
H42 H 0.440978 0.534244 0.763402 0.050 Uiso 1 1 calc R U . . .
C43 C 0.73233(13) 0.25993(11) 0.96654(7) 0.0334(3) Uani 1 1 d . . . . .
C44 C 0.71920(14) 0.18125(12) 1.01614(8) 0.0383(3) Uani 1 1 d . . . . .
H44 H 0.628579 0.139834 1.022771 0.046 Uiso 1 1 calc R U . . .
C45 C 0.83667(16) 0.16248(14) 1.05603(9) 0.0456(3) Uani 1 1 d . . . . .
H45 H 0.825902 0.108363 1.089634 0.055 Uiso 1 1 calc R U . . .
C46 C 0.96938(15) 0.22212(14) 1.04714(9) 0.0462(3) Uani 1 1 d . . . . .
H46 H 1.049709 0.208567 1.074142 0.055 Uiso 1 1 calc R U . . .
C47 C 0.98405(15) 0.30134(14) 0.99880(8) 0.0443(3) Uani 1 1 d . . . . .
H47 H 1.075234 0.343612 0.993127 0.053 Uiso 1 1 calc R U . . .
C48 C 0.86717(14) 0.32010(13) 0.95830(8) 0.0394(3) Uani 1 1 d . . . . .
H48 H 0.878804 0.374206 0.924731 0.047 Uiso 1 1 calc R U . . .
O2 O 0.000(2) 0.5070(12) 0.5022(9) 0.0719(10) Uani 0.5 1 d D U P A -1
O3 O 0.0508(4) 0.4063(3) 0.40093(19) 0.0859(9) Uani 0.5 1 d D U P A -1
C1 C -0.1891(8) 0.4012(8) 0.3971(6) 0.085(2) Uani 0.5 1 d D U P A -1
H1A H -0.243848 0.331509 0.416166 0.128 Uiso 0.5 1 calc R U P A -1
H1B H -0.207458 0.369207 0.342679 0.128 Uiso 0.5 1 calc R U P A -1
H1C H -0.216731 0.481297 0.410135 0.128 Uiso 0.5 1 calc R U P A -1
C3 C -0.0351(5) 0.4343(3) 0.4314(3) 0.0677(10) Uani 0.5 1 d D U P A -1
C7 C 0.1465(5) 0.5420(4) 0.5433(3) 0.0679(10) Uani 0.5 1 d D U P A -1
H7A H 0.210670 0.589407 0.516731 0.082 Uiso 0.5 1 calc R U P A -1
H7B H 0.169027 0.460103 0.547565 0.082 Uiso 0.5 1 calc R U P A -1
C11 C 0.1651(10) 0.6292(8) 0.6189(4) 0.080(2) Uani 0.5 1 d D U P A -1
H11A H 0.135650 0.706570 0.614138 0.120 Uiso 0.5 1 calc R U P A -1
H11B H 0.264607 0.659757 0.645978 0.120 Uiso 0.5 1 calc R U P A -1
H11C H 0.107392 0.578878 0.646435 0.120 Uiso 0.5 1 calc R U P A -1
O1 O 0.4456(5) 0.5231(3) 0.4796(2) 0.0663(10) Uani 0.5 1 d D U P B -1
O4 O 0.4760(9) 0.3474(7) 0.4074(5) 0.135(3) Uani 0.5 1 d D U P B -1
C1A C 0.4131(7) 0.4273(6) 0.4147(4) 0.0850(19) Uani 0.5 1 d D U P B -1
C1B C 0.5645(7) 0.5350(7) 0.5412(5) 0.0724(17) Uani 0.5 1 d D U P B -1
H1BA H 0.551259 0.449112 0.554131 0.087 Uiso 0.5 1 calc R U P B -1
H1BB H 0.654837 0.560076 0.526357 0.087 Uiso 0.5 1 calc R U P B -1
C1C C 0.5650(8) 0.6384(9) 0.6045(5) 0.075(2) Uani 0.5 1 d D U P B -1
H1CA H 0.577902 0.722577 0.590810 0.112 Uiso 0.5 1 calc R U P B -1
H1CB H 0.642486 0.650064 0.646890 0.112 Uiso 0.5 1 calc R U P B -1
H1CC H 0.475114 0.612119 0.618547 0.112 Uiso 0.5 1 calc R U P B -1
C12 C 0.2978(7) 0.4342(5) 0.3596(3) 0.120(2) Uani 0.5 1 d D U P B -1
H12A H 0.215987 0.430556 0.380857 0.180 Uiso 0.5 1 calc R U P B -1
H12B H 0.272192 0.358636 0.315116 0.180 Uiso 0.5 1 calc R U P B -1
H12C H 0.327662 0.517989 0.345666 0.180 Uiso 0.5 1 calc R U P B -1
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
C2 O7 C8 117.35(10) . . ?
C2 N1 C6 115.68(10) . . ?
C2 N3 C4 115.85(11) . . ?
C10 N12 H12 116.8 . . ?
C10 N12 C13 126.37(11) . . ?
C13 N12 H12 116.8 . . ?
C19 N20 C21 118.32(10) . . ?
N1 C2 O7 112.98(10) . . ?
N3 C2 O7 118.99(11) . . ?
N3 C2 N1 128.04(12) . . ?
N3 C4 C5 121.77(11) . . ?
N3 C4 C19 115.17(11) . . ?
C5 C4 C19 123.02(11) . . ?
C4 C5 C6 116.75(11) . . ?
C4 C5 C10 121.64(11) . . ?
C6 C5 C10 121.00(11) . . ?
N1 C6 C5 121.59(12) . . ?
N1 C6 C9 115.71(11) . . ?
C5 C6 C9 122.66(12) . . ?
O7 C8 H8A 109.5 . . ?
O7 C8 H8B 109.5 . . ?
O7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O11 C10 N12 125.12(12) . . ?
O11 C10 C5 119.53(12) . . ?
N12 C10 C5 115.32(11) . . ?
C14 C13 N12 118.32(12) . . ?
C18 C13 N12 122.32(12) . . ?
C18 C13 C14 119.34(12) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.86(14) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.79(14) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 120.5 . . ?
C17 C16 C15 119.06(14) . . ?
C17 C16 H16 120.5 . . ?
C16 C17 H17 119.4 . . ?
C16 C17 C18 121.16(14) . . ?
C18 C17 H17 119.4 . . ?
C13 C18 H18 120.1 . . ?
C17 C18 C13 119.73(14) . . ?
C17 C18 H18 120.1 . . ?
N20 C19 C4 115.86(10) . . ?
N20 C19 C24 123.14(11) . . ?
C24 C19 C4 120.98(11) . . ?
N20 C21 C22 122.08(11) . . ?
N20 C21 C25 115.81(10) . . ?
C22 C21 C25 122.10(11) . . ?
C21 C22 H22 120.5 . . ?
C23 C22 C21 119.03(11) . . ?
C23 C22 H22 120.5 . . ?
C22 C23 H23 120.4 . . ?
C22 C23 C24 119.26(12) . . ?
C24 C23 H23 120.4 . . ?
C19 C24 H24 120.9 . . ?
C23 C24 C19 118.16(12) . . ?
C23 C24 H24 120.9 . . ?
C26 C25 C21 120.29(11) . . ?
C30 C25 C21 120.26(11) . . ?
C30 C25 C26 119.44(11) . . ?
C25 C26 C31 121.00(11) . . ?
C27 C26 C25 119.76(11) . . ?
C27 C26 C31 119.18(11) . . ?
C26 C27 H27 119.3 . . ?
C26 C27 C28 121.39(11) . . ?
C28 C27 H27 119.3 . . ?
C27 C28 C43 122.11(11) . . ?
C29 C28 C27 118.04(11) . . ?
C29 C28 C43 119.85(11) . . ?
C28 C29 H29 118.8 . . ?
C30 C29 C28 122.46(11) . . ?
C30 C29 H29 118.8 . . ?
C25 C30 C37 123.23(11) . . ?
C29 C30 C25 118.88(11) . . ?
C29 C30 C37 117.85(11) . . ?
C32 C31 C26 119.98(11) . . ?
C36 C31 C26 121.59(13) . . ?
C36 C31 C32 118.40(13) . . ?
C31 C32 H32 119.2 . . ?
C33 C32 C31 121.56(15) . . ?
C33 C32 H32 119.2 . . ?
C32 C33 H33 120.2 . . ?
C34 C33 C32 119.68(17) . . ?
C34 C33 H33 120.2 . . ?
C33 C34 H34 120.0 . . ?
C33 C34 C35 120.05(15) . . ?
C35 C34 H34 120.0 . . ?
C34 C35 H35 119.7 . . ?
C34 C35 C36 120.52(16) . . ?
C36 C35 H35 119.7 . . ?
C31 C36 C35 119.76(16) . . ?
C31 C36 H36 120.1 . . ?
C35 C36 H36 120.1 . . ?
C38 C37 C30 119.29(11) . . ?
C38 C37 C42 118.48(12) . . ?
C42 C37 C30 122.13(11) . . ?
C37 C38 H38 119.6 . . ?
C39 C38 C37 120.85(13) . . ?
C39 C38 H38 119.6 . . ?
C38 C39 H39 119.9 . . ?
C40 C39 C38 120.30(13) . . ?
C40 C39 H39 119.9 . . ?
C39 C40 H40 120.3 . . ?
C39 C40 C41 119.49(13) . . ?
C41 C40 H40 120.3 . . ?
C40 C41 H41 119.7 . . ?
C40 C41 C42 120.52(14) . . ?
C42 C41 H41 119.7 . . ?
C37 C42 H42 119.8 . . ?
C41 C42 C37 120.36(13) . . ?
C41 C42 H42 119.8 . . ?
C44 C43 C28 121.30(12) . . ?
C44 C43 C48 118.22(12) . . ?
C48 C43 C28 120.43(12) . . ?
C43 C44 H44 119.6 . . ?
C45 C44 C43 120.87(13) . . ?
C45 C44 H44 119.6 . . ?
C44 C45 H45 119.8 . . ?
C46 C45 C44 120.34(14) . . ?
C46 C45 H45 119.8 . . ?
C45 C46 H46 120.3 . . ?
C47 C46 C45 119.40(13) . . ?
C47 C46 H46 120.3 . . ?
C46 C47 H47 119.6 . . ?
C46 C47 C48 120.71(13) . . ?
C48 C47 H47 119.6 . . ?
C43 C48 H48 119.8 . . ?
C47 C48 C43 120.46(13) . . ?
C47 C48 H48 119.8 . . ?
C3 O2 C7 117.1(17) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
O2 C3 C1 111.3(11) . . ?
O3 C3 O2 121.8(11) . . ?
O3 C3 C1 126.8(5) . . ?
O2 C7 H7A 110.0 . . ?
O2 C7 H7B 110.0 . . ?
O2 C7 C11 108.3(9) . . ?
H7A C7 H7B 108.4 . . ?
C11 C7 H7A 110.0 . . ?
C11 C7 H7B 110.0 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C1A O1 C1B 119.7(6) . . ?
O1 C1A C12 112.1(6) . . ?
O4 C1A O1 120.7(8) . . ?
O4 C1A C12 127.2(8) . . ?
O1 C1B H1BA 110.4 . . ?
O1 C1B H1BB 110.4 . . ?
H1BA C1B H1BB 108.6 . . ?
C1C C1B O1 106.5(6) . . ?
C1C C1B H1BA 110.4 . . ?
C1C C1B H1BB 110.4 . . ?
C1B C1C H1CA 109.5 . . ?
C1B C1C H1CB 109.5 . . ?
C1B C1C H1CC 109.5 . . ?
H1CA C1C H1CB 109.5 . . ?
H1CA C1C H1CC 109.5 . . ?
H1CB C1C H1CC 109.5 . . ?
C1A C12 H12A 109.5 . . ?
C1A C12 H12B 109.5 . . ?
C1A C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
O7 C2 1.3369(16) . ?
O7 C8 1.4417(18) . ?
O11 C10 1.2190(16) . ?
N1 C2 1.3363(17) . ?
N1 C6 1.3413(17) . ?
N3 C2 1.3229(16) . ?
N3 C4 1.3422(16) . ?
N12 H12 0.8800 . ?
N12 C10 1.3562(17) . ?
N12 C13 1.4161(16) . ?
N20 C19 1.3384(16) . ?
N20 C21 1.3384(15) . ?
C4 C5 1.3975(18) . ?
C4 C19 1.4879(17) . ?
C5 C6 1.4009(18) . ?
C5 C10 1.5098(18) . ?
C6 C9 1.4991(19) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C13 C14 1.393(2) . ?
C13 C18 1.390(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.386(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.381(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.378(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.385(2) . ?
C18 H18 0.9500 . ?
C19 C24 1.3885(18) . ?
C21 C22 1.3950(18) . ?
C21 C25 1.4858(17) . ?
C22 H22 0.9500 . ?
C22 C23 1.3786(19) . ?
C23 H23 0.9500 . ?
C23 C24 1.3848(19) . ?
C24 H24 0.9500 . ?
C25 C26 1.4117(17) . ?
C25 C30 1.4074(17) . ?
C26 C27 1.3897(18) . ?
C26 C31 1.4939(17) . ?
C27 H27 0.9500 . ?
C27 C28 1.3950(18) . ?
C28 C29 1.3906(18) . ?
C28 C43 1.4837(18) . ?
C29 H29 0.9500 . ?
C29 C30 1.3904(18) . ?
C30 C37 1.4948(17) . ?
C31 C32 1.392(2) . ?
C31 C36 1.3833(19) . ?
C32 H32 0.9500 . ?
C32 C33 1.381(2) . ?
C33 H33 0.9500 . ?
C33 C34 1.366(3) . ?
C34 H34 0.9500 . ?
C34 C35 1.378(3) . ?
C35 H35 0.9500 . ?
C35 C36 1.400(2) . ?
C36 H36 0.9500 . ?
C37 C38 1.3921(18) . ?
C37 C42 1.3944(19) . ?
C38 H38 0.9500 . ?
C38 C39 1.3840(19) . ?
C39 H39 0.9500 . ?
C39 C40 1.381(2) . ?
C40 H40 0.9500 . ?
C40 C41 1.382(2) . ?
C41 H41 0.9500 . ?
C41 C42 1.388(2) . ?
C42 H42 0.9500 . ?
C43 C44 1.3913(19) . ?
C43 C48 1.3980(19) . ?
C44 H44 0.9500 . ?
C44 C45 1.3866(19) . ?
C45 H45 0.9500 . ?
C45 C46 1.383(2) . ?
C46 H46 0.9500 . ?
C46 C47 1.377(2) . ?
C47 H47 0.9500 . ?
C47 C48 1.387(2) . ?
C48 H48 0.9500 . ?
O2 C3 1.331(16) . ?
O2 C7 1.458(19) . ?
O3 C3 1.198(5) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C3 1.498(8) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C11 1.485(7) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
O1 C1A 1.350(7) . ?
O1 C1B 1.482(6) . ?
O4 C1A 1.210(10) . ?
C1A C12 1.457(8) . ?
C1B H1BA 0.9900 . ?
C1B H1BB 0.9900 . ?
C1B C1C 1.455(9) . ?
C1C H1CA 0.9800 . ?
C1C H1CB 0.9800 . ?
C1C H1CC 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
N3 C4 C5 C6 3.47(17) . . . . ?
N3 C4 C5 C10 174.61(11) . . . . ?
N3 C4 C19 N20 156.09(11) . . . . ?
N3 C4 C19 C24 -25.48(17) . . . . ?
N12 C13 C14 C15 178.87(12) . . . . ?
N12 C13 C18 C17 -179.49(13) . . . . ?
N20 C19 C24 C23 1.3(2) . . . . ?
N20 C21 C22 C23 0.7(2) . . . . ?
N20 C21 C25 C26 -61.77(15) . . . . ?
N20 C21 C25 C30 116.64(12) . . . . ?
C2 N1 C6 C5 3.41(17) . . . . ?
C2 N1 C6 C9 -174.26(11) . . . . ?
C2 N3 C4 C5 1.39(17) . . . . ?
C2 N3 C4 C19 179.39(10) . . . . ?
C4 N3 C2 O7 175.56(11) . . . . ?
C4 N3 C2 N1 -4.55(19) . . . . ?
C4 C5 C6 N1 -6.00(17) . . . . ?
C4 C5 C6 C9 171.51(11) . . . . ?
C4 C5 C10 O11 -76.96(16) . . . . ?
C4 C5 C10 N12 104.92(13) . . . . ?
C4 C19 C24 C23 -177.05(12) . . . . ?
C5 C4 C19 N20 -25.94(17) . . . . ?
C5 C4 C19 C24 152.49(13) . . . . ?
C6 N1 C2 O7 -177.95(10) . . . . ?
C6 N1 C2 N3 2.15(19) . . . . ?
C6 C5 C10 O11 93.81(15) . . . . ?
C6 C5 C10 N12 -84.31(14) . . . . ?
C8 O7 C2 N1 176.76(12) . . . . ?
C8 O7 C2 N3 -3.33(18) . . . . ?
C10 N12 C13 C14 -167.37(12) . . . . ?
C10 N12 C13 C18 14.19(19) . . . . ?
C10 C5 C6 N1 -177.21(11) . . . . ?
C10 C5 C6 C9 0.31(18) . . . . ?
C13 N12 C10 O11 10.7(2) . . . . ?
C13 N12 C10 C5 -171.27(11) . . . . ?
C13 C14 C15 C16 1.1(2) . . . . ?
C14 C13 C18 C17 2.1(2) . . . . ?
C14 C15 C16 C17 1.0(2) . . . . ?
C15 C16 C17 C18 -1.6(2) . . . . ?
C16 C17 C18 C13 0.0(2) . . . . ?
C18 C13 C14 C15 -2.6(2) . . . . ?
C19 N20 C21 C22 -0.24(18) . . . . ?
C19 N20 C21 C25 -179.11(10) . . . . ?
C19 C4 C5 C6 -174.37(11) . . . . ?
C19 C4 C5 C10 -3.22(18) . . . . ?
C21 N20 C19 C4 177.65(10) . . . . ?
C21 N20 C19 C24 -0.74(18) . . . . ?
C21 C22 C23 C24 -0.1(2) . . . . ?
C21 C25 C26 C27 179.22(11) . . . . ?
C21 C25 C26 C31 -3.64(17) . . . . ?
C21 C25 C30 C29 179.70(11) . . . . ?
C21 C25 C30 C37 -2.66(18) . . . . ?
C22 C21 C25 C26 119.35(13) . . . . ?
C22 C21 C25 C30 -62.23(17) . . . . ?
C22 C23 C24 C19 -0.8(2) . . . . ?
C25 C21 C22 C23 179.46(12) . . . . ?
C25 C26 C27 C28 0.94(18) . . . . ?
C25 C26 C31 C32 -59.60(16) . . . . ?
C25 C26 C31 C36 122.35(14) . . . . ?
C25 C30 C37 C38 134.50(13) . . . . ?
C25 C30 C37 C42 -49.24(19) . . . . ?
C26 C25 C30 C29 -1.87(17) . . . . ?
C26 C25 C30 C37 175.77(11) . . . . ?
C26 C27 C28 C29 -1.55(18) . . . . ?
C26 C27 C28 C43 177.44(11) . . . . ?
C26 C31 C32 C33 -178.33(13) . . . . ?
C26 C31 C36 C35 179.70(14) . . . . ?
C27 C26 C31 C32 117.56(14) . . . . ?
C27 C26 C31 C36 -60.50(17) . . . . ?
C27 C28 C29 C30 0.43(18) . . . . ?
C27 C28 C43 C44 -41.84(17) . . . . ?
C27 C28 C43 C48 141.04(13) . . . . ?
C28 C29 C30 C25 1.27(18) . . . . ?
C28 C29 C30 C37 -176.49(11) . . . . ?
C28 C43 C44 C45 -177.51(12) . . . . ?
C28 C43 C48 C47 177.14(11) . . . . ?
C29 C28 C43 C44 137.13(13) . . . . ?
C29 C28 C43 C48 -39.98(17) . . . . ?
C29 C30 C37 C38 -47.84(17) . . . . ?
C29 C30 C37 C42 128.42(14) . . . . ?
C30 C25 C26 C27 0.80(17) . . . . ?
C30 C25 C26 C31 177.93(11) . . . . ?
C30 C37 C38 C39 175.91(12) . . . . ?
C30 C37 C42 C41 -176.22(13) . . . . ?
C31 C26 C27 C28 -176.24(11) . . . . ?
C31 C32 C33 C34 -1.3(2) . . . . ?
C32 C31 C36 C35 1.6(2) . . . . ?
C32 C33 C34 C35 1.3(3) . . . . ?
C33 C34 C35 C36 0.1(3) . . . . ?
C34 C35 C36 C31 -1.6(3) . . . . ?
C36 C31 C32 C33 -0.2(2) . . . . ?
C37 C38 C39 C40 0.6(2) . . . . ?
C38 C37 C42 C41 0.1(2) . . . . ?
C38 C39 C40 C41 -0.3(2) . . . . ?
C39 C40 C41 C42 -0.1(2) . . . . ?
C40 C41 C42 C37 0.2(2) . . . . ?
C42 C37 C38 C39 -0.5(2) . . . . ?
C43 C28 C29 C30 -178.59(11) . . . . ?
C43 C44 C45 C46 0.1(2) . . . . ?
C44 C43 C48 C47 -0.07(18) . . . . ?
C44 C45 C46 C47 0.6(2) . . . . ?
C45 C46 C47 C48 -1.0(2) . . . . ?
C46 C47 C48 C43 0.7(2) . . . . ?
C48 C43 C44 C45 -0.33(19) . . . . ?
C3 O2 C7 C11 176.6(6) . . . . ?
C7 O2 C3 O3 -5.0(11) . . . . ?
C7 O2 C3 C1 177.6(5) . . . . ?
C1A O1 C1B C1C -175.3(6) . . . . ?
C1B O1 C1A O4 3.1(8) . . . . ?
C1B O1 C1A C12 -177.5(4) . . . . ?
