#------------------------------------------------------------------------------
#$Date: 2020-04-28 23:31:32 +0300 (Tue, 28 Apr 2020) $
#$Revision: 251241 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/83/4038305.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_4038305
loop_
_publ_author_name
'Del Corte, Xabier'
'López-Francés, Adrián'
'Maestro, Aitor'
'Martinez de Marigorta, Edorta'
'Palacios, Francisco'
'Vicario, Javier'
_publ_section_title
;
 Brönsted Acid Catalyzed Multicomponent Synthesis of Phosphorus and
 Fluorine-Derived γ-Lactam Derivatives.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00280
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C26 H24 N2 O'
_chemical_formula_sum            'C26 H24 N2 O'
_chemical_formula_weight         380.47
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-12-02T16:57:55-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 115.110(12)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.2516(13)
_cell_length_b                   7.1055(5)
_cell_length_c                   13.0019(12)
_cell_measurement_reflns_used    3222
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      74.067
_cell_measurement_theta_min      3.732
_cell_volume                     1024.90(19)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2012
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1
_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     -3.00  22.00   1.00    4.00    --   36.00  96.00 122.98   25
  2  ω     -4.00  21.00   1.00    4.00    --   36.00  97.00 -26.02   25
  3  ω    -95.00 -14.00   1.00    4.00    --  -41.88 -57.00  30.00   81
  4  ω    -53.00 -17.00   1.00    4.00    --  -41.88 -38.00  60.00   36
  5  ω    -74.00  31.00   1.00    4.00    --  -41.88  77.00-180.00  105
  6  ω   -117.00  -2.00   1.00    4.00    --  -41.88 -19.00 150.00  115
  7  ω      9.00  40.00   1.00    4.00    --   41.88  77.00-150.00   31
  8  ω     80.00 108.00   1.00    4.00    --   41.88  77.00-150.00   28
  9  ω      3.00  98.00   1.00    4.00    --   41.88-125.00  30.00   95
 10  ω     14.00  40.00   1.00    4.00    --   48.00  83.00-106.02   26
 11  ω     14.00  39.00   1.00    4.00    --   48.00  81.00-161.33   25
 12  ω     19.00  44.00   1.00    4.00    --   52.00  80.00 -21.35   25
 13  ω     19.00  44.00   1.00    4.00    --   52.00  80.00  83.18   25
 14  ω     19.00  44.00   1.00    4.00    --   52.00  80.00  10.44   25
 15  ω     19.00  44.00   1.00    4.00    --   52.00  80.00 148.42   25
 16  ω     24.00  61.00   1.00    4.00    --   56.00  77.00-113.15   37
 17  ω     33.00  58.00   1.00    4.00    --   64.00  75.00 103.01   25
 18  ω     85.00 119.00   1.00    4.00    --   64.00  75.00 103.01   34
 19  ω     35.00  61.00   1.00    4.00    --   68.00  77.00   0.11   26
 20  ω     36.00  64.00   1.00    4.00    --   68.00  73.00 133.45   28
 21  ω     40.00  68.00   1.00    4.00    --   68.00  69.00-154.15   28
 22  ω     35.00  61.00   1.00    4.00    --   68.00  77.00 168.59   26
 23  ω     37.00  64.00   1.00    4.00    --   68.00  76.00 -90.97   27
 24  ω     36.00  61.00   1.00    4.00    --   68.00  77.00 -67.67   25
 25  ω     35.00  62.00   1.00    4.00    --   68.00  77.00  67.55   27
 26  ω     91.00 139.00   1.00    4.00    --   68.00  69.00-154.15   48
 27  ω    105.00 147.00   1.00    4.00    --   72.00  75.00-127.88   42
 28  ω     41.00  66.00   1.00    4.00    --   72.00  75.00-127.88   25
 29  ω     41.00  66.00   1.00    4.00    --   72.00  76.00 -47.08   25
 30  ω     40.00  66.00   1.00    4.00    --   72.00  75.00  28.57   26
 31  ω     43.00  73.00   1.00    4.00    --   72.00  69.00 175.01   30
 32  ω     49.00 102.00   1.00   16.00    --   80.00  71.00 -46.03   53
 33  ω     53.00  81.00   1.00   16.00    --   84.00  76.00  49.56   28
 34  ω    100.00 158.00   1.00   16.00    --   84.00  74.00  32.03   58
 35  ω     53.00  78.00   1.00   16.00    --   84.00  74.00  32.03   25
 36  ω     58.00  83.00   1.00   16.00    --   88.00  69.00-127.35   25
 37  ω     63.00  88.00   1.00   16.00    --   88.00  61.00  -3.41   25
 38  ω     57.00  89.00   1.00   16.00    --   88.00  70.00  81.90   32
 39  ω     60.00  93.00   1.00   16.00    --   92.00  76.00-110.75   33
 40  ω     74.00 107.00   1.00   16.00    --  104.00  66.00 109.97   33
 41  ω     29.00 109.00   1.00   16.00    --  109.18 -94.00 120.00   80
 42  ω     39.00 121.00   1.00   16.00    --  109.18 -61.00 -30.00   82
 43  ω     84.00 156.00   1.00   16.00    --  109.18  77.00 150.00   72
 44  ω     80.00 113.00   1.00   16.00    --  109.18  61.00 150.00   33
 45  ω    119.00 157.00   1.00   16.00    --  109.18  61.00  90.00   38
 46  ω     41.00  70.00   1.00   16.00    --  109.18 -45.00 120.00   29
 47  ω     77.00 150.00   1.00   16.00    --  109.18  77.00 -90.00   73
 48  ω     36.00  77.00   1.00   16.00    --  109.18 -45.00 -90.00   41
 49  ω     78.00 158.00   1.00   16.00    --  109.18  77.00-150.00   80
 50  ω     40.00  74.00   1.00   16.00    --  109.18 -45.00  90.00   34
 51  ω     77.00 145.00   1.00   16.00    --  109.18  77.00  30.00   68
 52  ω     41.00  85.00   1.00   16.00    --  109.18-118.00-122.00   44
 53  ω     80.00 107.00   1.00   16.00    --  109.18  61.00   0.00   27
 54  ω     85.00 112.00   1.00   16.00    --  109.18  61.00  90.00   27
 55  ω     72.00 108.00   1.00   16.00    --  109.18 -94.00  30.00   36
 56  ω     77.00 147.00   1.00   16.00    --  109.18  77.00 -60.00   70
 57  ω     77.00 158.00   1.00   16.00    --  109.18  77.00-180.00   81
 58  ω     41.00 124.00   1.00   16.00    --  109.18-133.00 -61.00   83
 59  ω     82.00 109.00   1.00   16.00    --  109.18  61.00-180.00   27
 60  ω     78.00 156.00   1.00   16.00    --  109.18  77.00   0.00   78
 61  ω     83.00 150.00   1.00   16.00    --  109.18  77.00-120.00   67
 62  ω    111.00 148.00   1.00   16.00    --  109.18  77.00  60.00   37
 63  ω     77.00 103.00   1.00   16.00    --  109.18  77.00  60.00   26
 64  ω     77.00 158.00   1.00   16.00    --  109.18  77.00 120.00   81
 65  ω    109.00 156.00   1.00   16.00    --  109.18  77.00 -30.00   47
 66  ω     77.00 103.00   1.00   16.00    --  109.18  77.00 -30.00   26
 67  ω     27.00 106.00   1.00   16.00    --  109.18 -94.00 -60.00   79
;
_diffrn_measurement_device       'four-circleκ-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0671699
_diffrn_orient_matrix_UB_12      -0.0449129
_diffrn_orient_matrix_UB_13      0.0739338
_diffrn_orient_matrix_UB_21      0.0016547
_diffrn_orient_matrix_UB_22      0.2103362
_diffrn_orient_matrix_UB_23      0.0294371
_diffrn_orient_matrix_UB_31      -0.12151
_diffrn_orient_matrix_UB_32      0.0273678
_diffrn_orient_matrix_UB_33      -0.1038686
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.102
_diffrn_reflns_av_unetI/netI     0.1625
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17410
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69
_diffrn_reflns_theta_min         3.755
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.590
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  0.907
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
       CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_description       prism
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.243
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.076
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 979 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3794
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0537
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0484P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1279
_reflns_Friedel_coverage         0.834
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                2855
_reflns_number_total             3794
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00280_si_005.cif
_cod_data_source_block           a20190401_xd373b4
_cod_original_cell_volume        1024.89(16)
_cod_database_code               4038305
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.5833(2) -0.0739(6) -0.9220(2) 0.0408(7) Uani 1 1 d . . . . .
N1 N -0.3901(3) -0.0793(6) -0.7866(3) 0.0330(7) Uani 1 1 d . . . . .
H1 H -0.315433 -0.093181 -0.778434 0.04 Uiso 1 1 calc R . . . .
N2 N -0.3059(3) -0.0882(7) -0.9388(3) 0.0376(8) Uani 1 1 d . . . . .
C1 C -0.4754(3) -0.0803(7) -0.8946(3) 0.0309(8) Uani 1 1 d . . . . .
C2 C -0.4209(3) -0.0887(7) -0.9806(3) 0.0316(9) Uani 1 1 d . . . . .
C3 C -0.4991(3) -0.0948(7) -1.1020(3) 0.0320(9) Uani 1 1 d . . . . .
H3 H -0.459938 -0.122322 -1.149537 0.038 Uiso 1 1 calc R . . . .
C4 C -0.6184(4) -0.0669(7) -1.1559(3) 0.0323(9) Uani 1 1 d . . . . .
H4 H -0.662904 -0.040175 -1.113021 0.039 Uiso 1 1 calc R . . . .
C5 C -0.6803(3) -0.0770(7) -1.2780(3) 0.0321(8) Uani 1 1 d . . . . .
H5 H -0.635237 -0.117024 -1.318137 0.038 Uiso 1 1 calc R . . . .
C6 C -0.7963(4) -0.0343(6) -1.3389(3) 0.0325(10) Uani 1 1 d . . . . .
H6 H -0.84159 0.002168 -1.298301 0.039 Uiso 1 1 calc R . . . .
C7 C -0.8597(4) -0.0389(6) -1.4633(3) 0.0307(9) Uani 1 1 d . . . . .
C8 C -0.9769(4) 0.0302(6) -1.5164(4) 0.0377(10) Uani 1 1 d . . . . .
H8 H -1.014755 0.079783 -1.471847 0.045 Uiso 1 1 calc R . . . .
C9 C -1.0393(4) 0.0270(7) -1.6345(4) 0.0426(11) Uani 1 1 d . . . . .
H9 H -1.119044 0.075285 -1.669819 0.051 Uiso 1 1 calc R . . . .
C10 C -0.9861(4) -0.0454(7) -1.7001(4) 0.0437(12) Uani 1 1 d . . . . .
H10 H -1.029022 -0.048641 -1.78045 0.052 Uiso 1 1 calc R . . . .
C11 C -0.8689(4) -0.1139(7) -1.6477(4) 0.0447(12) Uani 1 1 d . . . . .
H11 H -0.831387 -0.162892 -1.692681 0.054 Uiso 1 1 calc R . . . .
C12 C -0.8068(4) -0.1112(7) -1.5314(4) 0.0366(10) Uani 1 1 d . . . . .
H12 H -0.726901 -0.159153 -1.496823 0.044 Uiso 1 1 calc R . . . .
C13 C -0.4042(4) -0.0591(6) -0.6852(3) 0.0306(9) Uani 1 1 d . . . . .
C14 C -0.3058(4) -0.1037(6) -0.5841(3) 0.0342(10) Uani 1 1 d . . . . .
H14 H -0.234327 -0.152231 -0.585821 0.041 Uiso 1 1 calc R . . . .
C15 C -0.3118(4) -0.0773(8) -0.4809(3) 0.0369(9) Uani 1 1 d . . . . .
H15 H -0.243868 -0.10812 -0.412559 0.044 Uiso 1 1 calc R . . . .
C16 C -0.4143(4) -0.0073(6) -0.4751(4) 0.0360(10) Uani 1 1 d . . . . .
C17 C -0.5127(4) 0.0327(6) -0.5767(4) 0.0381(11) Uani 1 1 d . . . . .
H17 H -0.584865 0.077365 -0.574637 0.046 Uiso 1 1 calc R . . . .
C18 C -0.5090(4) 0.0093(6) -0.6812(4) 0.0366(10) Uani 1 1 d . . . . .
H18 H -0.577263 0.03968 -0.749376 0.044 Uiso 1 1 calc R . . . .
C19 C -0.4191(5) 0.0244(7) -0.3625(4) 0.0468(12) Uani 1 1 d . . . . .
H19A H -0.408544 -0.095912 -0.322588 0.07 Uiso 1 1 calc GR . . . .
H19B H -0.497338 0.078785 -0.375276 0.07 Uiso 1 1 calc GR . . . .
H19C H -0.354583 0.111041 -0.316458 0.07 Uiso 1 1 calc GR . . . .
C20 C -0.2424(3) -0.0823(8) -1.0086(3) 0.0354(9) Uani 1 1 d . . . . .
C21 C -0.2021(5) 0.0886(7) -1.0293(4) 0.0424(12) Uani 1 1 d . . . . .
H21 H -0.223996 0.201645 -1.003864 0.051 Uiso 1 1 calc R . . . .
C22 C -0.1301(5) 0.0959(7) -1.0869(4) 0.0414(12) Uani 1 1 d . . . . .
H22 H -0.103004 0.214916 -1.10007 0.05 Uiso 1 1 calc R . . . .
C23 C -0.0962(4) -0.0641(8) -1.1259(3) 0.0380(10) Uani 1 1 d . . . . .
C24 C -0.1404(5) -0.2356(7) -1.1074(5) 0.0433(12) Uani 1 1 d . . . . .
H24 H -0.120174 -0.347974 -1.134872 0.052 Uiso 1 1 calc R . . . .
C25 C -0.2132(5) -0.2462(8) -1.0500(5) 0.0441(12) Uani 1 1 d . . . . .
H25 H -0.24288 -0.364418 -1.039063 0.053 Uiso 1 1 calc R . . . .
C26 C -0.0134(4) -0.0565(9) -1.1850(4) 0.0485(12) Uani 1 1 d . . . . .
H26A H -0.050843 0.019066 -1.254278 0.073 Uiso 1 1 calc GR . . . .
H26B H 0.000976 -0.184381 -1.204691 0.073 Uiso 1 1 calc GR . . . .
H26C H 0.06352 0.000725 -1.134197 0.073 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 0 -4 0.0793
5 1 4 0.039
-5 1 -3 0.071
3 0 -4 0.0394
6 -1 2 0.0235
-6 0 8 0.0329
2 1 2 0.0456
-1 5 0 0.1209
-2 -1 -2 0.085
1 -5 0 0.109
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
C1 N1 H1 115.6 . . ?
C1 N1 C13 128.8(3) . . ?
C13 N1 H1 115.6 . . ?
C2 N2 C20 122.1(3) . . ?
O1 C1 N1 124.9(3) . . ?
O1 C1 C2 123.1(3) . . ?
N1 C1 C2 112.1(3) . . ?
N2 C2 C1 115.8(3) . . ?
N2 C2 C3 124.0(3) . . ?
C3 C2 C1 120.2(3) . . ?
C2 C3 H3 115.4 . . ?
C4 C3 C2 129.1(3) . . ?
C4 C3 H3 115.4 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 121.1(3) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 117.6 . . ?
C6 C5 C4 124.9(3) . . ?
C6 C5 H5 117.6 . . ?
C5 C6 H6 117.2 . . ?
C5 C6 C7 125.5(4) . . ?
C7 C6 H6 117.2 . . ?
C8 C7 C6 119.4(4) . . ?
C8 C7 C12 118.3(4) . . ?
C12 C7 C6 122.3(4) . . ?
C7 C8 H8 119.7 . . ?
C7 C8 C9 120.5(4) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.4(4) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.4(4) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.6(4) . . ?
C12 C11 H11 119.7 . . ?
C7 C12 H12 119.6 . . ?
C11 C12 C7 120.8(4) . . ?
C11 C12 H12 119.6 . . ?
C14 C13 N1 117.3(3) . . ?
C14 C13 C18 119.2(4) . . ?
C18 C13 N1 123.5(4) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.1(4) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 119.2 . . ?
C16 C15 C14 121.6(4) . . ?
C16 C15 H15 119.2 . . ?
C15 C16 C17 117.6(4) . . ?
C15 C16 C19 121.2(4) . . ?
C17 C16 C19 121.1(4) . . ?
C16 C17 H17 119 . . ?
C18 C17 C16 122.0(4) . . ?
C18 C17 H17 119 . . ?
C13 C18 H18 120.3 . . ?
C17 C18 C13 119.4(4) . . ?
C17 C18 H18 120.3 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 N2 119.2(5) . . ?
C21 C20 C25 119.2(3) . . ?
C25 C20 N2 121.4(5) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.3(5) . . ?
C22 C21 H21 119.9 . . ?
C21 C22 H22 119 . . ?
C21 C22 C23 122.0(5) . . ?
C23 C22 H22 119 . . ?
C22 C23 C24 117.2(4) . . ?
C22 C23 C26 122.0(5) . . ?
C24 C23 C26 120.8(5) . . ?
C23 C24 H24 119.1 . . ?
C25 C24 C23 121.7(5) . . ?
C25 C24 H24 119.1 . . ?
C20 C25 H25 120.2 . . ?
C24 C25 C20 119.5(5) . . ?
C24 C25 H25 120.2 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 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 C1 1.215(5) . ?
N1 H1 0.88 . ?
N1 C1 1.348(5) . ?
N1 C13 1.409(5) . ?
N2 C2 1.277(5) . ?
N2 C20 1.425(5) . ?
C1 C2 1.527(5) . ?
C2 C3 1.459(5) . ?
C3 H3 0.95 . ?
C3 C4 1.341(5) . ?
C4 H4 0.95 . ?
C4 C5 1.441(5) . ?
C5 H5 0.95 . ?
C5 C6 1.335(6) . ?
C6 H6 0.95 . ?
C6 C7 1.468(6) . ?
C7 C8 1.392(6) . ?
C7 C12 1.398(6) . ?
C8 H8 0.95 . ?
C8 C9 1.395(7) . ?
C9 H9 0.95 . ?
C9 C10 1.374(7) . ?
C10 H10 0.95 . ?
C10 C11 1.390(7) . ?
C11 H11 0.95 . ?
C11 C12 1.375(6) . ?
C12 H12 0.95 . ?
C13 C14 1.391(6) . ?
C13 C18 1.394(6) . ?
C14 H14 0.95 . ?
C14 C15 1.388(5) . ?
C15 H15 0.95 . ?
C15 C16 1.382(6) . ?
C16 C17 1.389(7) . ?
C16 C19 1.506(6) . ?
C17 H17 0.95 . ?
C17 C18 1.389(6) . ?
C18 H18 0.95 . ?
C19 H19A 0.98 . ?
C19 H19B 0.98 . ?
C19 H19C 0.98 . ?
C20 C21 1.380(7) . ?
C20 C25 1.392(7) . ?
C21 H21 0.95 . ?
C21 C22 1.378(7) . ?
C22 H22 0.95 . ?
C22 C23 1.379(7) . ?
C23 C24 1.395(7) . ?
C23 C26 1.511(5) . ?
C24 H24 0.95 . ?
C24 C25 1.386(7) . ?
C25 H25 0.95 . ?
C26 H26A 0.98 . ?
C26 H26B 0.98 . ?
C26 H26C 0.98 . ?
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
O1 C1 C2 N2 177.7(5) . . . . ?
O1 C1 C2 C3 -1.7(8) . . . . ?
N1 C1 C2 N2 -1.9(7) . . . . ?
N1 C1 C2 C3 178.7(4) . . . . ?
N1 C13 C14 C15 176.6(5) . . . . ?
N1 C13 C18 C17 -177.0(4) . . . . ?
N2 C2 C3 C4 -168.6(5) . . . . ?
N2 C20 C21 C22 173.4(5) . . . . ?
N2 C20 C25 C24 -173.2(4) . . . . ?
C1 N1 C13 C14 166.3(5) . . . . ?
C1 N1 C13 C18 -16.3(8) . . . . ?
C1 C2 C3 C4 10.8(8) . . . . ?
C2 N2 C20 C21 96.3(6) . . . . ?
C2 N2 C20 C25 -88.0(6) . . . . ?
C2 C3 C4 C5 179.3(5) . . . . ?
C3 C4 C5 C6 -173.5(5) . . . . ?
C4 C5 C6 C7 178.2(5) . . . . ?
C5 C6 C7 C8 -172.5(4) . . . . ?
C5 C6 C7 C12 7.7(7) . . . . ?
C6 C7 C8 C9 -179.9(4) . . . . ?
C6 C7 C12 C11 179.8(4) . . . . ?
C7 C8 C9 C10 0.4(7) . . . . ?
C8 C7 C12 C11 0.1(7) . . . . ?
C8 C9 C10 C11 -0.7(7) . . . . ?
C9 C10 C11 C12 0.6(7) . . . . ?
C10 C11 C12 C7 -0.4(7) . . . . ?
C12 C7 C8 C9 -0.1(7) . . . . ?
C13 N1 C1 O1 -4.5(9) . . . . ?
C13 N1 C1 C2 175.0(5) . . . . ?
C13 C14 C15 C16 0.1(7) . . . . ?
C14 C13 C18 C17 0.4(6) . . . . ?
C14 C15 C16 C17 1.3(7) . . . . ?
C14 C15 C16 C19 -178.8(5) . . . . ?
C15 C16 C17 C18 -1.9(7) . . . . ?
C16 C17 C18 C13 1.0(7) . . . . ?
C18 C13 C14 C15 -1.0(7) . . . . ?
C19 C16 C17 C18 178.2(4) . . . . ?
C20 N2 C2 C1 -175.5(5) . . . . ?
C20 N2 C2 C3 3.8(8) . . . . ?
C20 C21 C22 C23 0.2(8) . . . . ?
C21 C20 C25 C24 2.5(7) . . . . ?
C21 C22 C23 C24 1.6(7) . . . . ?
C21 C22 C23 C26 -177.6(5) . . . . ?
C22 C23 C24 C25 -1.5(7) . . . . ?
C23 C24 C25 C20 -0.6(8) . . . . ?
C25 C20 C21 C22 -2.3(7) . . . . ?
C26 C23 C24 C25 177.8(5) . . . . ?
