#------------------------------------------------------------------------------
#$Date: 2024-11-04 13:26:57 +0200 (Mon, 04 Nov 2024) $
#$Revision: 295758 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/30/1573026.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_1573026
loop_
_publ_author_name
'Roper, Natalie J.'
'Campbell, Aaron D. G.'
'Waddell, Paul G.'
'Brown, Alistair K.'
'Ermanis, Kristaps'
'Armstrong, Roly J.'
_publ_section_title
;
 A stereodivergent multicomponent approach for the synthesis of C-N
 atropisomeric peptide analogues.
;
_journal_issue                   40
_journal_name_full               'Chemical science'
_journal_page_first              16743
_journal_page_last               16751
_journal_paper_doi               10.1039/d4sc04700a
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C29 H34 N2 O2'
_chemical_formula_sum            'C29 H34 N2 O2'
_chemical_formula_weight         442.58
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-01-16
_audit_creation_method
;
Olex2 1.3
(compiled 2020.12.01 svn.r5f60950 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-05-15 deposited with the CCDC.	2024-09-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.9500(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.1161(2)
_cell_length_b                   12.9639(2)
_cell_length_c                   14.5367(2)
_cell_measurement_reflns_used    18194
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      77.8860
_cell_measurement_theta_min      3.9050
_cell_volume                     2581.75(7)
_computing_cell_refinement       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -63.00 -23.00   0.50    0.46    --  -92.01  77.00 -60.00   80
  2  ω    -47.00 -21.00   0.50    0.46    --  -92.01  45.00-120.00   52
  3  ω    -51.00 -26.00   0.50    0.46    --  -92.01  45.00 -60.00   50
  4  ω    -49.00 -15.00   0.50    0.46    --  -92.01  45.00-150.00   68
  5  ω    -47.00 -22.00   0.50    0.46    --  -92.01  45.00  60.00   50
  6  ω    -46.00 -20.00   0.50    0.46    --  -92.01  45.00  90.00   52
  7  ω    -71.00 -43.00   0.50    0.46    --  -92.01  61.00 150.00   56
  8  ω    -51.00 -16.00   0.50    0.46    --  -92.01  45.00 150.00   70
  9  ω    -51.00 -19.00   0.50    0.46    --  -92.01  45.00 120.00   64
 10  ω    -27.00  22.00   0.50    0.46    --  -49.76  19.00 -60.00   98
 11  ω    -12.00  28.00   0.50    0.46    --  -49.76  19.00-120.00   80
 12  ω    -26.00  28.00   0.50    0.46    --  -49.76  19.00 120.00  108
 13  ω     80.00 109.00   0.50    0.46    --   48.76 123.00 -67.00   58
 14  ω    102.00 127.00   0.50    0.46    --  108.00 123.00 -67.00   50
 15  ω     86.00 111.00   0.50    0.46    --  108.00 150.00  94.00   50
 16  ω     58.00 118.00   0.50    0.46    --   48.76 150.00  94.00  120
 17  ω     78.00 121.00   0.50    0.46    --   48.76 125.00  90.00   86
 18  ω     76.00 114.00   0.50    0.46    --   96.11  61.00  90.00   76
 19  ω    126.00 155.00   0.50    0.46    --   96.11  61.00  90.00   58
 20  ω     48.00  73.00   0.50    0.46    --  108.00 -95.00-120.00   50
 21  ω     73.00  98.00   0.50    0.46    --  108.00-123.00-148.00   50
 22  ω     36.00  80.00   0.50    0.46    --   48.76-123.00-148.00   88
 23  ω     60.00  85.00   0.50    0.46    --  108.00-150.00  49.00   50
 24  ω     73.00 101.00   0.50    0.46    --  108.00-125.00 150.00   56
 25  ω     37.00  63.00   0.50    0.46    --  108.00-125.00 150.00   52
 26  ω    -30.00  22.00   0.50    0.46    --   48.76 -19.00  90.00  104
 27  ω     18.00  51.00   0.50    0.46    --   96.11 -45.00   0.00   66
 28  ω     43.00  70.00   0.50    0.46    --  108.00 -77.00  30.00   54
 29  ω     24.00  50.00   0.50    0.46    --   96.11 -45.00  90.00   52
 30  ω     20.00  45.00   0.50    0.46    --   96.11 -45.00  30.00   50
 31  ω     37.00  62.00   0.50    0.46    --  108.00 -61.00 -30.00   50
 32  ω     57.00 102.00   0.50    0.46    --  108.00 -77.00 -60.00   90
 33  ω     44.00  69.00   0.50    0.46    --  108.00 -61.00-180.00   50
 34  ω    -27.00  38.00   0.50    0.46    --   48.76 -38.00-180.00  130
 35  ω   -164.00 -40.00   0.50    0.46    --  -92.01 -15.00 -30.00  248
 36  ω   -112.00 -87.00   0.50    0.46    --  -49.76-150.00  49.00   50
 37  ω   -133.00-108.00   0.50    0.46    --  -92.01-150.00  49.00   50
 38  ω   -137.00-112.00   0.50    0.46    --  -92.01-123.00-148.00   50
 39  ω   -107.00 -33.00   0.50    0.46    --  -99.00 105.00 -43.54  148
 40  ω    -65.00 -40.00   0.50    0.46    --  -92.01 123.00 -67.00   50
 41  ω   -107.00 -33.00   0.50    0.46    --  -99.00 108.00-111.72  148
 42  ω    -59.00 -34.00   0.50    0.46    --  -49.76 123.00 -67.00   50
 43  ω   -108.00 -52.00   0.50    0.46    --  -99.00 109.00  49.44  112
 44  ω   -129.00 -52.00   0.50    0.46    --  -92.01 150.00  94.00  154
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1014876000
_diffrn_orient_matrix_UB_12      0.0365167000
_diffrn_orient_matrix_UB_13      -0.0085071000
_diffrn_orient_matrix_UB_21      -0.0362482000
_diffrn_orient_matrix_UB_22      0.1125520000
_diffrn_orient_matrix_UB_23      -0.0082445000
_diffrn_orient_matrix_UB_31      0.0323905000
_diffrn_orient_matrix_UB_32      0.0114192000
_diffrn_orient_matrix_UB_33      0.1084123000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            30909
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.327
_diffrn_reflns_theta_min         3.918
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.555
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_correction_T_min  0.935
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.139
_exptl_crystal_description       prism
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.00119(17)
_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   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         5208
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0387
_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)+(0.0486P)²+0.6746P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1042
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4592
_reflns_number_total             5208
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc04700a3.cif
_cod_data_source_block           rja230005_fa
_cod_database_code               1573026
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C29 H34 N2 O2'
_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   0.952
_shelx_estimated_absorpt_t_min   0.902
_reflns_odcompleteness_completeness 99.98
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C15(H15), C16(H16), C17(H17),
 C18(H18), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C20(H20A,H20B,
 H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.309
_oxdiff_exptl_absorpt_empirical_full_min 0.710
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.41180(6) 0.72715(7) 0.26614(6) 0.0358(2) Uani 1 1 d . . . . .
O2 O 0.62242(6) 0.53484(8) 0.50468(6) 0.0402(2) Uani 1 1 d . . . . .
N1 N 0.33567(7) 0.63158(8) 0.35781(7) 0.0301(2) Uani 1 1 d . . . . .
H1 H 0.3433(10) 0.5786(11) 0.3971(10) 0.036 Uiso 1 1 d . U . . .
N2 N 0.58998(6) 0.62028(7) 0.36437(6) 0.0243(2) Uani 1 1 d . . . . .
C1 C 0.40936(8) 0.65294(9) 0.31755(8) 0.0267(2) Uani 1 1 d . . . . .
C2 C 0.49098(8) 0.57229(9) 0.33753(8) 0.0264(2) Uani 1 1 d . . . . .
H2 H 0.482824 0.529795 0.392519 0.032 Uiso 1 1 calc R U . . .
C3 C 0.48434(8) 0.49975(9) 0.25387(8) 0.0288(2) Uani 1 1 d . . . . .
C4 C 0.43478(9) 0.52469(10) 0.16191(9) 0.0335(3) Uani 1 1 d . . . . .
H4 H 0.396231 0.585539 0.150323 0.040 Uiso 1 1 calc R U . . .
C5 C 0.44136(9) 0.46104(11) 0.08685(10) 0.0407(3) Uani 1 1 d . . . . .
H5 H 0.407119 0.478543 0.024189 0.049 Uiso 1 1 calc R U . . .
C6 C 0.49731(10) 0.37253(11) 0.10264(11) 0.0469(4) Uani 1 1 d . . . . .
H6 H 0.503402 0.330492 0.050842 0.056 Uiso 1 1 calc R U . . .
C7 C 0.54441(10) 0.34538(11) 0.19417(12) 0.0480(4) Uani 1 1 d . . . . .
H7 H 0.581749 0.283704 0.205503 0.058 Uiso 1 1 calc R U . . .
C8 C 0.53724(9) 0.40807(10) 0.26951(10) 0.0383(3) Uani 1 1 d . . . . .
H8 H 0.568700 0.388283 0.332379 0.046 Uiso 1 1 calc R U . . .
C9 C 0.24411(9) 0.69147(11) 0.34273(9) 0.0385(3) Uani 1 1 d . . . . .
C10 C 0.18361(11) 0.64204(14) 0.40400(12) 0.0597(5) Uani 1 1 d . . . . .
H10A H 0.170445 0.569903 0.385024 0.089 Uiso 1 1 calc R U . . .
H10B H 0.121739 0.679280 0.395937 0.089 Uiso 1 1 calc R U . . .
H10C H 0.219568 0.644980 0.470643 0.089 Uiso 1 1 calc R U . . .
C11 C 0.18883(11) 0.68262(18) 0.23903(12) 0.0692(6) Uani 1 1 d . . . . .
H11A H 0.229949 0.708228 0.198437 0.104 Uiso 1 1 calc R U . . .
H11B H 0.128891 0.723715 0.228243 0.104 Uiso 1 1 calc R U . . .
H11C H 0.172141 0.610215 0.223780 0.104 Uiso 1 1 calc R U . . .
C12 C 0.26529(14) 0.80271(14) 0.37040(19) 0.0826(7) Uani 1 1 d . . . . .
H12A H 0.301563 0.806450 0.436904 0.124 Uiso 1 1 calc R U . . .
H12B H 0.203713 0.840569 0.362133 0.124 Uiso 1 1 calc R U . . .
H12C H 0.304352 0.833431 0.330162 0.124 Uiso 1 1 calc R U . . .
C13 C 0.62182(7) 0.69190(8) 0.30148(7) 0.0239(2) Uani 1 1 d . . . . .
C14 C 0.63576(8) 0.79773(9) 0.32168(8) 0.0279(2) Uani 1 1 d . . . . .
C15 C 0.67394(9) 0.85460(9) 0.25659(9) 0.0344(3) Uani 1 1 d . . . . .
H15 H 0.686157 0.926010 0.268544 0.041 Uiso 1 1 calc R U . . .
C16 C 0.69470(9) 0.81299(10) 0.17654(8) 0.0351(3) Uani 1 1 d . . . . .
H16 H 0.720857 0.855185 0.135255 0.042 Uiso 1 1 calc R U . . .
C17 C 0.67727(8) 0.70947(10) 0.15655(8) 0.0312(3) Uani 1 1 d . . . . .
H17 H 0.689591 0.679956 0.100757 0.037 Uiso 1 1 calc R U . . .
C18 C 0.64157(8) 0.64988(9) 0.21938(7) 0.0265(2) Uani 1 1 d . . . . .
H18 H 0.630109 0.578513 0.206547 0.032 Uiso 1 1 calc R U . . .
C19 C 0.61337(10) 0.86134(9) 0.40396(9) 0.0357(3) Uani 1 1 d . . . . .
C20 C 0.57099(10) 0.80288(10) 0.47676(9) 0.0393(3) Uani 1 1 d . . . . .
H20A H 0.511312 0.766854 0.444089 0.059 Uiso 1 1 calc R U . . .
H20B H 0.555696 0.851874 0.522458 0.059 Uiso 1 1 calc R U . . .
H20C H 0.618906 0.752590 0.510215 0.059 Uiso 1 1 calc R U . . .
C21 C 0.70843(12) 0.91322(12) 0.45914(10) 0.0517(4) Uani 1 1 d . . . . .
H21A H 0.757295 0.860153 0.484161 0.078 Uiso 1 1 calc R U . . .
H21B H 0.695259 0.953493 0.511739 0.078 Uiso 1 1 calc R U . . .
H21C H 0.733149 0.958979 0.416587 0.078 Uiso 1 1 calc R U . . .
C22 C 0.53752(12) 0.94468(11) 0.36008(11) 0.0501(4) Uani 1 1 d . . . . .
H22A H 0.564268 0.988786 0.317741 0.075 Uiso 1 1 calc R U . . .
H22B H 0.522435 0.986763 0.410720 0.075 Uiso 1 1 calc R U . . .
H22C H 0.477775 0.911310 0.323974 0.075 Uiso 1 1 calc R U . . .
C23 C 0.65169(8) 0.58660(9) 0.44590(8) 0.0274(2) Uani 1 1 d . . . . .
C24 C 0.75869(8) 0.60984(8) 0.46383(7) 0.0253(2) Uani 1 1 d . . . . .
C25 C 0.80841(9) 0.64578(10) 0.55250(8) 0.0339(3) Uani 1 1 d . . . . .
H25 H 0.773169 0.662166 0.598612 0.041 Uiso 1 1 calc R U . . .
C26 C 0.90913(9) 0.65793(10) 0.57422(9) 0.0358(3) Uani 1 1 d . . . . .
H26 H 0.942349 0.684850 0.634097 0.043 Uiso 1 1 calc R U . . .
C27 C 0.96073(9) 0.63075(9) 0.50848(8) 0.0323(3) Uani 1 1 d . . . . .
H27 H 1.029714 0.638056 0.523489 0.039 Uiso 1 1 calc R U . . .
C28 C 0.91239(8) 0.59298(9) 0.42095(8) 0.0313(3) Uani 1 1 d . . . . .
H28 H 0.948270 0.573332 0.376242 0.038 Uiso 1 1 calc R U . . .
C29 C 0.81170(8) 0.58366(8) 0.39820(8) 0.0263(2) Uani 1 1 d . . . . .
H29 H 0.778665 0.559215 0.337303 0.032 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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 1 0 0.0467
-1 -1 0 0.0457
-1 0 1 0.0749
1 0 -1 0.0709
1 0 0 0.0535
-1 0 0 0.0535
1 0 1 0.0615
-1 0 -1 0.0635
1 -1 1 0.0555
-1 1 -1 0.0535
0 -1 -1 0.0524
0 -1 0 0.0534
0 1 0 0.0534
0 -1 1 0.0655
1 -1 -1 0.0601
-1 1 1 0.0711
1 -1 0 0.0469
-1 1 0 0.0509
1 1 -1 0.0606
-1 -1 1 0.0626
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 117.2(9) . . ?
C1 N1 C9 124.75(10) . . ?
C9 N1 H1 118.0(9) . . ?
C13 N2 C2 121.03(8) . . ?
C23 N2 C2 117.10(9) . . ?
C23 N2 C13 121.59(9) . . ?
O1 C1 N1 124.64(10) . . ?
O1 C1 C2 121.48(9) . . ?
N1 C1 C2 113.83(9) . . ?
N2 C2 C1 112.28(9) . . ?
N2 C2 H2 107.6 . . ?
N2 C2 C3 109.85(8) . . ?
C1 C2 H2 107.6 . . ?
C3 C2 C1 111.82(9) . . ?
C3 C2 H2 107.6 . . ?
C4 C3 C2 123.00(10) . . ?
C4 C3 C8 118.78(11) . . ?
C8 C3 C2 118.00(11) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.27(12) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.48(13) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 H6 120.2 . . ?
C5 C6 C7 119.66(13) . . ?
C7 C6 H6 120.2 . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C8 120.09(13) . . ?
C8 C7 H7 120.0 . . ?
C3 C8 H8 119.7 . . ?
C7 C8 C3 120.62(13) . . ?
C7 C8 H8 119.7 . . ?
N1 C9 C10 106.68(10) . . ?
N1 C9 C11 109.13(11) . . ?
N1 C9 C12 110.66(12) . . ?
C10 C9 C11 108.80(13) . . ?
C12 C9 C10 110.55(14) . . ?
C12 C9 C11 110.91(15) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 N2 122.85(9) . . ?
C18 C13 N2 116.40(10) . . ?
C18 C13 C14 120.72(10) . . ?
C13 C14 C19 129.56(10) . . ?
C15 C14 C13 115.34(10) . . ?
C15 C14 C19 115.08(10) . . ?
C14 C15 H15 118.0 . . ?
C16 C15 C14 123.91(11) . . ?
C16 C15 H15 118.0 . . ?
C15 C16 H16 120.2 . . ?
C15 C16 C17 119.64(11) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 120.7 . . ?
C18 C17 C16 118.61(11) . . ?
C18 C17 H17 120.7 . . ?
C13 C18 H18 119.1 . . ?
C17 C18 C13 121.72(11) . . ?
C17 C18 H18 119.1 . . ?
C20 C19 C14 117.13(10) . . ?
C20 C19 C21 106.95(11) . . ?
C20 C19 C22 106.44(11) . . ?
C21 C19 C14 108.68(11) . . ?
C21 C19 C22 109.82(12) . . ?
C22 C19 C14 107.69(10) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O2 C23 N2 121.76(10) . . ?
O2 C23 C24 118.70(10) . . ?
N2 C23 C24 119.51(9) . . ?
C25 C24 C23 119.35(10) . . ?
C29 C24 C23 121.21(10) . . ?
C29 C24 C25 118.90(10) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 C24 120.57(11) . . ?
C26 C25 H25 119.7 . . ?
C25 C26 H26 120.1 . . ?
C27 C26 C25 119.73(11) . . ?
C27 C26 H26 120.1 . . ?
C26 C27 H27 119.9 . . ?
C26 C27 C28 120.19(11) . . ?
C28 C27 H27 119.9 . . ?
C27 C28 H28 119.9 . . ?
C27 C28 C29 120.12(11) . . ?
C29 C28 H28 119.9 . . ?
C24 C29 H29 119.8 . . ?
C28 C29 C24 120.44(10) . . ?
C28 C29 H29 119.8 . . ?
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 1.2237(13) . ?
O2 C23 1.2334(13) . ?
N1 H1 0.884(15) . ?
N1 C1 1.3396(14) . ?
N1 C9 1.4782(15) . ?
N2 C2 1.4931(13) . ?
N2 C13 1.4485(13) . ?
N2 C23 1.3625(14) . ?
C1 C2 1.5309(15) . ?
C2 H2 1.0000 . ?
C2 C3 1.5222(16) . ?
C3 C4 1.3893(17) . ?
C3 C8 1.3929(17) . ?
C4 H4 0.9500 . ?
C4 C5 1.3889(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.380(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.382(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.387(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.5166(18) . ?
C9 C11 1.526(2) . ?
C9 C12 1.508(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.4069(16) . ?
C13 C18 1.3996(15) . ?
C14 C15 1.4054(16) . ?
C14 C19 1.5468(16) . ?
C15 H15 0.9500 . ?
C15 C16 1.3767(18) . ?
C16 H16 0.9500 . ?
C16 C17 1.3826(18) . ?
C17 H17 0.9500 . ?
C17 C18 1.3809(15) . ?
C18 H18 0.9500 . ?
C19 C20 1.5355(18) . ?
C19 C21 1.5419(19) . ?
C19 C22 1.5464(19) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.5001(15) . ?
C24 C25 1.3911(16) . ?
C24 C29 1.3891(15) . ?
C25 H25 0.9500 . ?
C25 C26 1.3891(18) . ?
C26 H26 0.9500 . ?
C26 C27 1.3797(17) . ?
C27 H27 0.9500 . ?
C27 C28 1.3805(17) . ?
C28 H28 0.9500 . ?
C28 C29 1.3847(16) . ?
C29 H29 0.9500 . ?
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 47.97(14) . . . . ?
O1 C1 C2 C3 -76.05(13) . . . . ?
O2 C23 C24 C25 -47.47(16) . . . . ?
O2 C23 C24 C29 124.04(12) . . . . ?
N1 C1 C2 N2 -134.68(10) . . . . ?
N1 C1 C2 C3 101.30(11) . . . . ?
N2 C2 C3 C4 -104.08(12) . . . . ?
N2 C2 C3 C8 70.47(12) . . . . ?
N2 C13 C14 C15 175.33(9) . . . . ?
N2 C13 C14 C19 -6.03(18) . . . . ?
N2 C13 C18 C17 -176.56(10) . . . . ?
N2 C23 C24 C25 134.45(11) . . . . ?
N2 C23 C24 C29 -54.04(15) . . . . ?
C1 N1 C9 C10 -178.33(13) . . . . ?
C1 N1 C9 C11 64.29(17) . . . . ?
C1 N1 C9 C12 -58.02(18) . . . . ?
C1 C2 C3 C4 21.28(14) . . . . ?
C1 C2 C3 C8 -164.16(10) . . . . ?
C2 N2 C13 C14 110.86(12) . . . . ?
C2 N2 C13 C18 -71.16(13) . . . . ?
C2 N2 C23 O2 -14.09(16) . . . . ?
C2 N2 C23 C24 163.93(9) . . . . ?
C2 C3 C4 C5 171.99(10) . . . . ?
C2 C3 C8 C7 -171.55(11) . . . . ?
C3 C4 C5 C6 -0.16(18) . . . . ?
C4 C3 C8 C7 3.24(18) . . . . ?
C4 C5 C6 C7 2.2(2) . . . . ?
C5 C6 C7 C8 -1.5(2) . . . . ?
C6 C7 C8 C3 -1.3(2) . . . . ?
C8 C3 C4 C5 -2.52(17) . . . . ?
C9 N1 C1 O1 3.05(19) . . . . ?
C9 N1 C1 C2 -174.21(11) . . . . ?
C13 N2 C2 C1 -58.09(12) . . . . ?
C13 N2 C2 C3 67.02(12) . . . . ?
C13 N2 C23 O2 171.88(11) . . . . ?
C13 N2 C23 C24 -10.10(15) . . . . ?
C13 C14 C15 C16 1.69(17) . . . . ?
C13 C14 C19 C20 1.04(18) . . . . ?
C13 C14 C19 C21 122.31(13) . . . . ?
C13 C14 C19 C22 -118.78(13) . . . . ?
C14 C13 C18 C17 1.47(16) . . . . ?
C14 C15 C16 C17 0.41(19) . . . . ?
C15 C14 C19 C20 179.68(11) . . . . ?
C15 C14 C19 C21 -59.05(14) . . . . ?
C15 C14 C19 C22 59.86(14) . . . . ?
C15 C16 C17 C18 -1.64(17) . . . . ?
C16 C17 C18 C13 0.73(17) . . . . ?
C18 C13 C14 C15 -2.57(15) . . . . ?
C18 C13 C14 C19 176.07(11) . . . . ?
C19 C14 C15 C16 -177.15(11) . . . . ?
C23 N2 C2 C1 127.84(10) . . . . ?
C23 N2 C2 C3 -107.05(11) . . . . ?
C23 N2 C13 C14 -75.34(14) . . . . ?
C23 N2 C13 C18 102.65(12) . . . . ?
C23 C24 C25 C26 173.41(11) . . . . ?
C23 C24 C29 C28 -171.36(10) . . . . ?
C24 C25 C26 C27 -2.26(19) . . . . ?
C25 C24 C29 C28 0.19(17) . . . . ?
C25 C26 C27 C28 0.90(19) . . . . ?
C26 C27 C28 C29 0.98(18) . . . . ?
C27 C28 C29 C24 -1.54(17) . . . . ?
C29 C24 C25 C26 1.70(18) . . . . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0000 1.0000 -0.0000 0.1380 0.0763 0.0438
-1.0000 -1.0000 0.0000 -0.1380 -0.0763 -0.0438
-1.0000 -0.0000 1.0000 -0.1100 0.0280 0.0760
1.0000 0.0000 -1.0000 0.1100 -0.0280 -0.0760
1.0000 0.0000 -0.0000 0.1015 -0.0362 0.0324
-1.0000 -0.0000 0.0000 -0.1015 0.0362 -0.0324
1.0000 -0.0000 1.0000 0.0930 -0.0445 0.1408
-1.0000 0.0000 -1.0000 -0.0930 0.0445 -0.1408
1.0000 -1.0000 1.0000 0.0565 -0.1570 0.1294
-1.0000 1.0000 -1.0000 -0.0565 0.1570 -0.1294
-0.0000 -1.0000 -1.0000 -0.0280 -0.1043 -0.1198
-0.0000 -1.0000 0.0000 -0.0365 -0.1126 -0.0114
0.0000 1.0000 -0.0000 0.0365 0.1126 0.0114
0.0000 -1.0000 1.0000 -0.0450 -0.1208 0.0970
1.0000 -1.0000 -1.0000 0.0735 -0.1406 -0.0874
-1.0000 1.0000 1.0000 -0.0735 0.1406 0.0874
1.0000 -1.0000 -0.0000 0.0650 -0.1488 0.0210
-1.0000 1.0000 0.0000 -0.0650 0.1488 -0.0210
1.0000 1.0000 -1.0000 0.1465 0.0845 -0.0646
-1.0000 -1.0000 1.0000 -0.1465 -0.0845 0.0646
