#------------------------------------------------------------------------------
#$Date: 2024-11-04 12:26:57 +0100 (Mon 04 de Nov de 2024) $
#$Revision: 295758 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/30/1573027.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_1573027
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         'C33 H34 N2 O2'
_chemical_formula_sum            'C33 H34 N2 O2'
_chemical_formula_weight         490.62
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-09-10
_audit_creation_method
;
Olex2 1.5-ac5-023
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2024-09-10 deposited with the CCDC.	2024-09-16 downloaded from the CCDC.
;
_cell_angle_alpha                95.4770(10)
_cell_angle_beta                 94.5580(10)
_cell_angle_gamma                109.670(2)
_cell_formula_units_Z            2
_cell_length_a                   9.6100(2)
_cell_length_b                   9.7457(2)
_cell_length_c                   15.6810(3)
_cell_measurement_reflns_used    12839
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      75.4440
_cell_measurement_theta_min      2.8620
_cell_volume                     1366.82(5)
_computing_cell_refinement       'CrysAlisPro 1.171.43.126a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.126a 64-bit (release 11-06-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.126a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac5-023 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-023 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     55.00 105.00   0.50    0.61    --  108.12 -77.00 120.00  100
  2  ω     35.00 105.00   0.50    0.61    --  108.12 -95.00  30.00  140
  3  ω     24.00 105.00   0.50    0.61    --   97.16 -95.00 -30.00  162
  4  ω     31.00  71.00   0.50    0.61    --  108.12 -61.00 -90.00   80
  5  ω     16.00  51.00   0.50    0.61    --   97.16 -45.00-180.00   70
  6  ω     77.00 178.00   0.50    0.61    --  108.12  77.00-120.00  202
  7  ω     77.00 178.00   0.50    0.61    --  108.12  77.00-120.00  202
  8  ω     74.00 173.00   0.50    0.61    --   97.16 125.00-120.00  198
  9  ω     17.00  43.00   0.50    0.15    --   54.00  88.00 -89.85   52
 10  ω     16.00  43.00   0.50    0.15    --   54.00  89.00 -45.27   54
 11  ω    -48.00 -15.00   0.50    0.15    --   14.00 129.00 -53.02   66
 12  ω    -43.00  35.00   0.50    0.15    --  -47.30  38.00-180.00  156
 13  ω    -51.00 -11.00   0.50    0.61    --  -92.45  45.00   0.00   80
 14  ω    -51.00 -11.00   0.50    0.61    --  -92.45  45.00  30.00   80
 15  ω    -71.00 -15.00   0.50    0.61    --  -92.45  61.00 120.00  112
 16  ω   -112.00 -16.00   0.50    0.61    --  -92.45 125.00 120.00  192
 17  ω   -112.00 -16.00   0.50    0.61    --  -92.45 125.00 120.00  192
 18  ω   -152.00 -51.00   0.50    0.61    --  -78.00 -68.00  21.35  202
 19  ω   -166.00 -64.00   0.50    0.61    --  -90.00 -65.00  45.33  204
 20  ω   -152.00 -51.00   0.50    0.61    --  -78.00 -68.00  21.35  202
 21  ω   -158.00 -56.00   0.50    0.61    --  -86.00 -74.00 -43.71  204
 22  ω   -130.00  19.00   0.50    0.15    --  -47.30 -19.00   0.00  298
 23  ω   -121.00 -23.00   0.50    0.61    --  -99.00 138.00-151.67  196
 24  ω   -166.00 -64.00   0.50    0.61    --  -90.00 -65.00  45.33  204
 25  ω   -168.00 -73.00   0.50    0.61    --  -92.45-125.00  90.00  190
 26  ω   -166.00 -83.00   0.50    0.61    --  -92.45 -95.00  90.00  166
 27  ω   -166.00 -83.00   0.50    0.61    --  -92.45 -95.00-180.00  166
;
_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      0.1351535000
_diffrn_orient_matrix_UB_12      -0.0326957000
_diffrn_orient_matrix_UB_13      0.0402362000
_diffrn_orient_matrix_UB_21      -0.0836845000
_diffrn_orient_matrix_UB_22      -0.0519672000
_diffrn_orient_matrix_UB_23      0.0773694000
_diffrn_orient_matrix_UB_31      -0.0642614000
_diffrn_orient_matrix_UB_32      -0.1577881000
_diffrn_orient_matrix_UB_33      -0.0477033000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20367
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.454
_diffrn_reflns_theta_min         2.851
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.577
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.126a (Rigaku Oxford Diffraction, 2024)
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    1.192
_exptl_crystal_description       prism
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0024(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         5299
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0361
_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)+(0.0405P)²+0.4076P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0944
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4800
_reflns_number_total             5299
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc04700a3.cif
_cod_data_source_block           rja240026_fa
_cod_database_code               1573027
_chemical_oxdiff_formula         'C33 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   0.961
_shelx_estimated_absorpt_t_min   0.939
_diffrn_oxdiff_digest_frames
;
01399655a3b6f0558372be6fada5d7386904170bd0d
;
_diffrn_oxdiff_digest_hkl
;
011f43bb7b66decf5bb7005394145ed1974032
;
_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:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C22(H22), C24(H24), C27(H27), C28(H28), C29(H29), C30(H30),
  C31(H31)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C32(H32A,H32B,
 H32C), C33(H33A,H33B,H33C)
;
_shelx_shelxl_version_number     2019/1
_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 1.124
_oxdiff_exptl_absorpt_empirical_full_min 0.821
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
O1 O 0.50144(8) 0.46637(8) 0.73120(5) 0.02511(18) Uani 1 1 d . . . . .
O2 O 0.94938(9) 0.51476(10) 0.85359(6) 0.0355(2) Uani 1 1 d . . . . .
N1 N 0.72501(10) 0.64208(10) 0.72937(6) 0.0208(2) Uani 1 1 d . . . . .
N2 N 0.69848(11) 0.40311(11) 0.84798(6) 0.0245(2) Uani 1 1 d . . . . .
H2 H 0.6144(16) 0.3868(15) 0.8155(9) 0.029 Uiso 1 1 d . U . . .
C1 C 0.57489(12) 0.59800(12) 0.73319(7) 0.0215(2) Uani 1 1 d . . . . .
C2 C 0.49512(12) 0.70727(12) 0.74132(7) 0.0226(2) Uani 1 1 d . . . . .
C3 C 0.35855(13) 0.65645(13) 0.77473(7) 0.0275(3) Uani 1 1 d . . . . .
H3 H 0.324526 0.560128 0.790740 0.033 Uiso 1 1 calc R U . . .
C4 C 0.27245(13) 0.74430(15) 0.78478(8) 0.0333(3) Uani 1 1 d . . . . .
H4 H 0.180731 0.708721 0.808226 0.040 Uiso 1 1 calc R U . . .
C5 C 0.32014(14) 0.88405(15) 0.76062(9) 0.0344(3) Uani 1 1 d . . . . .
H5 H 0.261249 0.944610 0.767468 0.041 Uiso 1 1 calc R U . . .
C6 C 0.45422(14) 0.93560(14) 0.72634(8) 0.0320(3) Uani 1 1 d . . . . .
H6 H 0.486274 1.031053 0.709037 0.038 Uiso 1 1 calc R U . . .
C7 C 0.54164(13) 0.84842(13) 0.71724(8) 0.0269(2) Uani 1 1 d . . . . .
H7 H 0.633858 0.885097 0.694439 0.032 Uiso 1 1 calc R U . . .
C8 C 0.80039(12) 0.53105(12) 0.72751(7) 0.0217(2) Uani 1 1 d . . . . .
H8 H 0.903394 0.585422 0.714676 0.026 Uiso 1 1 calc R U . . .
C9 C 0.82270(12) 0.48200(12) 0.81702(7) 0.0235(2) Uani 1 1 d . . . . .
C10 C 0.73915(12) 0.40212(12) 0.65537(7) 0.0226(2) Uani 1 1 d . . . . .
C11 C 0.76583(14) 0.27227(13) 0.66524(8) 0.0285(3) Uani 1 1 d . . . . .
H11 H 0.810940 0.260861 0.718967 0.034 Uiso 1 1 calc R U . . .
C12 C 0.72690(15) 0.15943(13) 0.59705(9) 0.0347(3) Uani 1 1 d . . . . .
H12 H 0.745613 0.071362 0.604542 0.042 Uiso 1 1 calc R U . . .
C13 C 0.66123(14) 0.17394(14) 0.51839(8) 0.0346(3) Uani 1 1 d . . . . .
H13 H 0.634172 0.096229 0.472004 0.041 Uiso 1 1 calc R U . . .
C14 C 0.63536(13) 0.30305(14) 0.50803(8) 0.0318(3) Uani 1 1 d . . . . .
H14 H 0.591290 0.314412 0.453973 0.038 Uiso 1 1 calc R U . . .
C15 C 0.67337(12) 0.41629(13) 0.57614(8) 0.0265(2) Uani 1 1 d . . . . .
H15 H 0.654191 0.504047 0.568412 0.032 Uiso 1 1 calc R U . . .
C16 C 0.69175(14) 0.34032(14) 0.93052(7) 0.0286(3) Uani 1 1 d . . . . .
C17 C 0.77670(17) 0.23322(16) 0.93026(10) 0.0413(3) Uani 1 1 d . . . . .
H17A H 0.881854 0.286114 0.925614 0.062 Uiso 1 1 calc R U . . .
H17B H 0.734829 0.155980 0.881022 0.062 Uiso 1 1 calc R U . . .
H17C H 0.767961 0.188789 0.983973 0.062 Uiso 1 1 calc R U . . .
C18 C 0.75565(17) 0.46279(16) 1.00605(8) 0.0388(3) Uani 1 1 d . . . . .
H18A H 0.695721 0.526671 1.007437 0.058 Uiso 1 1 calc R U . . .
H18B H 0.858514 0.520620 0.999112 0.058 Uiso 1 1 calc R U . . .
H18C H 0.753768 0.419794 1.060132 0.058 Uiso 1 1 calc R U . . .
C19 C 0.52752(16) 0.25836(17) 0.93610(9) 0.0420(3) Uani 1 1 d . . . . .
H19A H 0.487200 0.180312 0.887166 0.063 Uiso 1 1 calc R U . . .
H19B H 0.473006 0.327057 0.934575 0.063 Uiso 1 1 calc R U . . .
H19C H 0.516748 0.215008 0.990150 0.063 Uiso 1 1 calc R U . . .
C20 C 0.82642(12) 0.79292(11) 0.74796(7) 0.0209(2) Uani 1 1 d . . . . .
C21 C 0.90097(12) 0.86135(12) 0.68158(7) 0.0212(2) Uani 1 1 d . . . . .
C22 C 1.00245(12) 1.00463(12) 0.70048(7) 0.0237(2) Uani 1 1 d . . . . .
H22 H 1.052298 1.051626 0.655575 0.028 Uiso 1 1 calc R U . . .
C23 C 1.03244(12) 1.08039(12) 0.78354(8) 0.0253(2) Uani 1 1 d . . . . .
C24 C 0.95836(13) 1.00879(12) 0.84793(7) 0.0254(2) Uani 1 1 d . . . . .
H24 H 0.978847 1.059062 0.904983 0.030 Uiso 1 1 calc R U . . .
C25 C 0.85519(13) 0.86620(12) 0.83235(7) 0.0244(2) Uani 1 1 d . . . . .
C26 C 0.87622(12) 0.78639(12) 0.59104(7) 0.0222(2) Uani 1 1 d . . . . .
C27 C 0.75545(13) 0.78070(13) 0.53335(8) 0.0270(2) Uani 1 1 d . . . . .
H27 H 0.686266 0.824087 0.551956 0.032 Uiso 1 1 calc R U . . .
C28 C 0.73508(14) 0.71244(14) 0.44913(8) 0.0319(3) Uani 1 1 d . . . . .
H28 H 0.652671 0.709708 0.410435 0.038 Uiso 1 1 calc R U . . .
C29 C 0.83503(15) 0.64838(14) 0.42164(8) 0.0329(3) Uani 1 1 d . . . . .
H29 H 0.820210 0.599794 0.364429 0.039 Uiso 1 1 calc R U . . .
C30 C 0.95656(14) 0.65532(14) 0.47772(8) 0.0317(3) Uani 1 1 d . . . . .
H30 H 1.025873 0.612486 0.458638 0.038 Uiso 1 1 calc R U . . .
C31 C 0.97777(13) 0.72456(13) 0.56175(8) 0.0269(2) Uani 1 1 d . . . . .
H31 H 1.062204 0.729812 0.599570 0.032 Uiso 1 1 calc R U . . .
C32 C 1.14147(14) 1.23598(13) 0.80348(9) 0.0347(3) Uani 1 1 d . . . . .
H32A H 1.089444 1.305017 0.793654 0.052 Uiso 1 1 calc R U . . .
H32B H 1.220464 1.249957 0.765832 0.052 Uiso 1 1 calc R U . . .
H32C H 1.185216 1.253880 0.863894 0.052 Uiso 1 1 calc R U . . .
C33 C 0.77920(16) 0.79790(14) 0.90610(8) 0.0361(3) Uani 1 1 d . . . . .
H33A H 0.824234 0.728070 0.925562 0.054 Uiso 1 1 calc R U . . .
H33B H 0.673117 0.746197 0.886894 0.054 Uiso 1 1 calc R U . . .
H33C H 0.790810 0.874987 0.953853 0.054 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
0 0 1 0.0397
0 0 -1 0.0397
0 -1 0 0.0433
0 1 0 0.0433
1 0 0 0.0316
-1 0 0 0.0376
1 -1 0 0.0528
-1 1 0 0.0528
-1 0 1 0.0446
1 0 -1 0.0306
-1 -1 1 0.0470
1 0 1 0.0327
-1 0 -1 0.0327
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 C8 119.52(9) . . ?
C1 N1 C20 124.82(9) . . ?
C20 N1 C8 113.93(8) . . ?
C9 N2 H2 116.2(9) . . ?
C9 N2 C16 125.84(10) . . ?
C16 N2 H2 117.9(9) . . ?
O1 C1 N1 120.15(10) . . ?
O1 C1 C2 118.29(10) . . ?
N1 C1 C2 121.55(9) . . ?
C3 C2 C1 114.78(10) . . ?
C7 C2 C1 126.85(10) . . ?
C7 C2 C3 118.35(11) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.05(11) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 119.90(11) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.86(12) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.33(12) . . ?
C7 C6 H6 119.8 . . ?
C2 C7 H7 119.8 . . ?
C6 C7 C2 120.49(11) . . ?
C6 C7 H7 119.8 . . ?
N1 C8 H8 104.6 . . ?
N1 C8 C9 112.69(9) . . ?
N1 C8 C10 116.12(9) . . ?
C9 C8 H8 104.6 . . ?
C10 C8 H8 104.6 . . ?
C10 C8 C9 112.82(9) . . ?
O2 C9 N2 124.95(11) . . ?
O2 C9 C8 119.13(10) . . ?
N2 C9 C8 115.91(9) . . ?
C11 C10 C8 119.09(10) . . ?
C15 C10 C8 121.73(10) . . ?
C15 C10 C11 118.71(10) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.42(12) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.66(12) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 120.4 . . ?
C12 C13 C14 119.18(11) . . ?
C14 C13 H13 120.4 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.50(12) . . ?
C15 C14 H14 119.8 . . ?
C10 C15 C14 120.53(11) . . ?
C10 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
N2 C16 C17 109.95(10) . . ?
N2 C16 C18 110.21(10) . . ?
N2 C16 C19 106.17(10) . . ?
C18 C16 C17 110.62(11) . . ?
C19 C16 C17 109.79(11) . . ?
C19 C16 C18 110.00(11) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
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 N1 119.19(9) . . ?
C25 C20 N1 120.08(10) . . ?
C25 C20 C21 120.64(10) . . ?
C20 C21 C26 122.52(10) . . ?
C22 C21 C20 118.99(10) . . ?
C22 C21 C26 118.49(10) . . ?
C21 C22 H22 119.2 . . ?
C23 C22 C21 121.60(10) . . ?
C23 C22 H22 119.2 . . ?
C22 C23 C32 121.38(11) . . ?
C24 C23 C22 117.94(10) . . ?
C24 C23 C32 120.68(11) . . ?
C23 C24 H24 118.6 . . ?
C23 C24 C25 122.73(11) . . ?
C25 C24 H24 118.6 . . ?
C20 C25 C33 122.91(10) . . ?
C24 C25 C20 118.09(10) . . ?
C24 C25 C33 119.00(10) . . ?
C27 C26 C21 121.55(10) . . ?
C31 C26 C21 119.93(10) . . ?
C31 C26 C27 118.49(10) . . ?
C26 C27 H27 119.6 . . ?
C28 C27 C26 120.88(11) . . ?
C28 C27 H27 119.6 . . ?
C27 C28 H28 120.0 . . ?
C29 C28 C27 119.91(12) . . ?
C29 C28 H28 120.0 . . ?
C28 C29 H29 120.1 . . ?
C30 C29 C28 119.81(11) . . ?
C30 C29 H29 120.1 . . ?
C29 C30 H30 119.8 . . ?
C29 C30 C31 120.35(11) . . ?
C31 C30 H30 119.8 . . ?
C26 C31 H31 119.7 . . ?
C30 C31 C26 120.53(11) . . ?
C30 C31 H31 119.7 . . ?
C23 C32 H32A 109.5 . . ?
C23 C32 H32B 109.5 . . ?
C23 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C25 C33 H33A 109.5 . . ?
C25 C33 H33B 109.5 . . ?
C25 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 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 1.2346(13) . ?
O2 C9 1.2269(14) . ?
N1 C1 1.3678(14) . ?
N1 C8 1.4905(14) . ?
N1 C20 1.4506(13) . ?
N2 H2 0.877(15) . ?
N2 C9 1.3407(15) . ?
N2 C16 1.4803(15) . ?
C1 C2 1.5090(15) . ?
C2 C3 1.4013(16) . ?
C2 C7 1.3953(16) . ?
C3 H3 0.9500 . ?
C3 C4 1.3836(17) . ?
C4 H4 0.9500 . ?
C4 C5 1.3836(19) . ?
C5 H5 0.9500 . ?
C5 C6 1.3883(18) . ?
C6 H6 0.9500 . ?
C6 C7 1.3872(17) . ?
C7 H7 0.9500 . ?
C8 H8 1.0000 . ?
C8 C9 1.5472(15) . ?
C8 C10 1.5264(15) . ?
C10 C11 1.3931(16) . ?
C10 C15 1.3888(16) . ?
C11 H11 0.9500 . ?
C11 C12 1.3885(17) . ?
C12 H12 0.9500 . ?
C12 C13 1.382(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.3838(19) . ?
C14 H14 0.9500 . ?
C14 C15 1.3906(17) . ?
C15 H15 0.9500 . ?
C16 C17 1.5262(17) . ?
C16 C18 1.5250(18) . ?
C16 C19 1.5242(18) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.4039(15) . ?
C20 C25 1.4022(15) . ?
C21 C22 1.3954(15) . ?
C21 C26 1.4958(15) . ?
C22 H22 0.9500 . ?
C22 C23 1.3922(16) . ?
C23 C24 1.3884(17) . ?
C23 C32 1.5109(16) . ?
C24 H24 0.9500 . ?
C24 C25 1.3939(16) . ?
C25 C33 1.5059(16) . ?
C26 C27 1.3959(16) . ?
C26 C31 1.3930(16) . ?
C27 H27 0.9500 . ?
C27 C28 1.3887(17) . ?
C28 H28 0.9500 . ?
C28 C29 1.3842(19) . ?
C29 H29 0.9500 . ?
C29 C30 1.3836(19) . ?
C30 H30 0.9500 . ?
C30 C31 1.3886(17) . ?
C31 H31 0.9500 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2 O1 0.877(15) 2.016(15) 2.7873(13) 146.1(13) . yes
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 C3 20.74(14) . . . . ?
O1 C1 C2 C7 -157.48(11) . . . . ?
N1 C1 C2 C3 -158.27(10) . . . . ?
N1 C1 C2 C7 23.50(17) . . . . ?
N1 C8 C9 O2 -112.83(11) . . . . ?
N1 C8 C9 N2 68.27(12) . . . . ?
N1 C8 C10 C11 -158.16(10) . . . . ?
N1 C8 C10 C15 29.76(14) . . . . ?
N1 C20 C21 C22 -177.71(9) . . . . ?
N1 C20 C21 C26 2.12(15) . . . . ?
N1 C20 C25 C24 177.22(10) . . . . ?
N1 C20 C25 C33 -3.09(17) . . . . ?
C1 N1 C8 C9 -76.34(12) . . . . ?
C1 N1 C8 C10 55.98(13) . . . . ?
C1 N1 C20 C21 -115.36(12) . . . . ?
C1 N1 C20 C25 68.03(14) . . . . ?
C1 C2 C3 C4 -179.22(11) . . . . ?
C1 C2 C7 C6 178.17(11) . . . . ?
C2 C3 C4 C5 0.83(19) . . . . ?
C3 C2 C7 C6 0.00(17) . . . . ?
C3 C4 C5 C6 0.0(2) . . . . ?
C4 C5 C6 C7 -0.9(2) . . . . ?
C5 C6 C7 C2 0.84(18) . . . . ?
C7 C2 C3 C4 -0.83(17) . . . . ?
C8 N1 C1 O1 -3.23(15) . . . . ?
C8 N1 C1 C2 175.77(9) . . . . ?
C8 N1 C20 C21 79.79(12) . . . . ?
C8 N1 C20 C25 -96.82(12) . . . . ?
C8 C10 C11 C12 -172.46(10) . . . . ?
C8 C10 C15 C14 171.94(10) . . . . ?
C9 N2 C16 C17 -60.21(15) . . . . ?
C9 N2 C16 C18 61.99(15) . . . . ?
C9 N2 C16 C19 -178.91(11) . . . . ?
C9 C8 C10 C11 -25.91(14) . . . . ?
C9 C8 C10 C15 162.02(10) . . . . ?
C10 C8 C9 O2 113.25(12) . . . . ?
C10 C8 C9 N2 -65.65(12) . . . . ?
C10 C11 C12 C13 0.02(19) . . . . ?
C11 C10 C15 C14 -0.17(17) . . . . ?
C11 C12 C13 C14 0.41(19) . . . . ?
C12 C13 C14 C15 -0.72(19) . . . . ?
C13 C14 C15 C10 0.60(18) . . . . ?
C15 C10 C11 C12 -0.14(17) . . . . ?
C16 N2 C9 O2 -0.79(18) . . . . ?
C16 N2 C9 C8 178.04(10) . . . . ?
C20 N1 C1 O1 -167.30(10) . . . . ?
C20 N1 C1 C2 11.70(16) . . . . ?
C20 N1 C8 C9 89.39(11) . . . . ?
C20 N1 C8 C10 -138.29(9) . . . . ?
C20 C21 C22 C23 0.66(16) . . . . ?
C20 C21 C26 C27 81.97(14) . . . . ?
C20 C21 C26 C31 -100.21(13) . . . . ?
C21 C20 C25 C24 0.65(16) . . . . ?
C21 C20 C25 C33 -179.66(11) . . . . ?
C21 C22 C23 C24 0.23(16) . . . . ?
C21 C22 C23 C32 -179.48(11) . . . . ?
C21 C26 C27 C28 179.11(11) . . . . ?
C21 C26 C31 C30 -179.67(10) . . . . ?
C22 C21 C26 C27 -98.20(13) . . . . ?
C22 C21 C26 C31 79.62(13) . . . . ?
C22 C23 C24 C25 -0.72(17) . . . . ?
C23 C24 C25 C20 0.28(17) . . . . ?
C23 C24 C25 C33 -179.42(11) . . . . ?
C25 C20 C21 C22 -1.11(16) . . . . ?
C25 C20 C21 C26 178.71(10) . . . . ?
C26 C21 C22 C23 -179.17(10) . . . . ?
C26 C27 C28 C29 0.29(18) . . . . ?
C27 C26 C31 C30 -1.78(17) . . . . ?
C27 C28 C29 C30 -1.34(18) . . . . ?
C28 C29 C30 C31 0.82(18) . . . . ?
C29 C30 C31 C26 0.76(18) . . . . ?
C31 C26 C27 C28 1.26(17) . . . . ?
C32 C23 C24 C25 178.99(11) . . . . ?
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
-0.0001 0.0003 0.9986 0.0402 0.0773 -0.0477
0.0001 -0.0003 -0.9986 -0.0402 -0.0773 0.0477
-0.0000 -0.9985 0.0002 0.0327 0.0519 0.1576
0.0000 0.9985 -0.0002 -0.0327 -0.0519 -0.1576
0.9988 0.0006 0.0002 0.1350 -0.0836 -0.0643
-0.9988 -0.0006 -0.0002 -0.1350 0.0836 0.0643
0.9987 -0.9980 0.0004 0.1676 -0.0317 0.0933
-0.9987 0.9980 -0.0004 -0.1676 0.0317 -0.0933
-0.9988 -0.0003 0.9983 -0.0948 0.1608 0.0166
0.9988 0.0003 -0.9983 0.0948 -0.1608 -0.0166
-0.9988 -0.9988 0.9985 -0.0622 0.2127 0.1742
0.9987 0.0008 0.9988 0.1751 -0.0063 -0.1120
-0.9987 -0.0008 -0.9988 -0.1751 0.0063 0.1120
