#------------------------------------------------------------------------------
#$Date: 2024-02-04 13:27:22 +0200 (Sun, 04 Feb 2024) $
#$Revision: 289401 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/05/1570591.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_1570591
loop_
_publ_author_name
'Waly, Sara M. A.'
'Benniston, Andrew C.'
'Harriman, Anthony'
_publ_section_title
;
 Deducing the conformational space for an octa-proline helix.
;
_journal_issue                   5
_journal_name_full               'Chemical science'
_journal_page_first              1657
_journal_page_last               1671
_journal_paper_doi               10.1039/d3sc05287g
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C31 H33 N3 O4'
_chemical_formula_sum            'C31 H33 N3 O4'
_chemical_formula_weight         511.60
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-12-09
_audit_creation_method
;
Olex2 1.3
(compiled 2020.12.01 svn.r5f60950 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-07-22 deposited with the CCDC.	2023-12-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.498(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.3503(2)
_cell_length_b                   8.7745(2)
_cell_length_c                   14.9164(3)
_cell_measurement_reflns_used    10914
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      77.4690
_cell_measurement_theta_min      3.0460
_cell_volume                     1311.55(5)
_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 0.937
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     70.00  96.00   0.50    1.64    --   48.76  28.00   8.00   52
  2  ω    -17.00   9.00   0.50    1.64    --   48.76 -28.00-153.00   52
  3  ω   -126.00 -26.00   0.50    1.64    --  -49.76 -28.00-153.00  200
  4  ω     -2.00  28.00   0.50    1.64    --  -49.76  28.00   8.00   60
  5  ω    -31.00  -6.00   0.50    1.64    --  -49.76  28.00   8.00   50
  6  ω   -105.00 -70.00   0.50    1.64    --  -92.01 -28.00-153.00   70
  7  ω     76.00 118.00   0.50    1.64    --   96.11  28.00   8.00   84
  8  ω     24.00  63.00   0.50    1.64    --   48.76  77.00  30.00   78
  9  ω    -30.00  27.00   0.50    1.64    --   48.76 -19.00  60.00  114
 10  ω     22.00  60.00   0.50    1.64    --   48.76  77.00  90.00   76
 11  ω    -84.00 -33.00   0.50    1.64    --  -49.76 -38.00 120.00  102
 12  ω     38.00  68.00   0.50    1.64    --   62.00  76.00 118.06   60
 13  ω    -83.00 -51.00   0.50    1.64    --  -62.00 -74.00  55.98   64
 14  ω    -78.00 -52.00   0.50    1.64    --  -74.00 -69.00 126.62   52
 15  ω    -85.00 -60.00   0.50    1.64    --  -82.00 -65.00 128.60   50
 16  ω    -87.00 -61.00   0.50    1.64    --  -86.00 -74.00 104.75   52
 17  ω   -124.00 -98.00   0.50    1.64    --  -86.00 -74.00 104.75   52
 18  ω    -88.00 -62.00   0.50    1.64    --  -86.00 -71.00  84.11   52
 19  ω   -154.00-104.00   0.50    1.64    --  -86.00 -56.00 145.33  100
 20  ω    -87.00 -62.00   0.50    1.64    --  -86.00 -72.00 106.37   50
 21  ω   -127.00 -66.00   0.50    1.64    --  -90.00 -72.00  82.80  122
 22  ω    -90.00 -65.00   0.50    1.64    --  -90.00 -73.00  75.05   50
 23  ω   -158.00-132.00   0.50    1.64    --  -90.00 -73.00  75.05   52
 24  ω   -110.00 -71.00   0.50    1.64    --  -92.01 -77.00-180.00   78
 25  ω   -159.00 -70.00   0.50    1.64    --  -92.01 -77.00  60.00  178
 26  ω    -85.00 -30.00   0.50    1.64    --  -92.01 125.00 120.00  110
 27  ω   -159.00 -68.00   0.50    1.64    --  -94.00 -77.00 133.88  182
 28  ω     19.00  50.00   0.50    1.64    --   96.11 -45.00 -30.00   62
 29  ω     23.00  49.00   0.50    1.64    --   96.11 -45.00-150.00   52
 30  ω     18.00  47.00   0.50    1.64    --   96.11 -45.00  60.00   58
 31  ω     26.00  51.00   0.50    1.64    --   96.11 -45.00  90.00   50
 32  ω     81.00 111.00   0.50    1.64    --   96.11-125.00-180.00   60
 33  ω     24.00  55.00   0.50    1.64    --   96.11-125.00-180.00   62
 34  ω     80.00 135.00   0.50    1.64    --   96.11  77.00 150.00  110
 35  ω     25.00  50.00   0.50    1.64    --   96.11 -45.00 -90.00   50
 36  ω     22.00  57.00   0.50    1.64    --   96.11 -61.00  30.00   70
 37  ω   -131.00 -75.00   0.50    1.64    --  -99.00 -74.00  75.49  112
 38  ω     43.00  83.00   0.50    1.64    --  108.00 -77.00 -90.00   80
 39  ω     41.00  66.00   0.50    1.64    --  108.00 -61.00-150.00   50
 40  ω     37.00  67.00   0.50    1.64    --  108.00 -61.00 120.00   60
 41  ω     39.00  71.00   0.50    1.64    --  108.00 -61.00  60.00   64
 42  ω    126.00 151.00   0.50    1.64    --  108.00  28.00   8.00   50
;
_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      0.0464037000
_diffrn_orient_matrix_UB_12      -0.0189745000
_diffrn_orient_matrix_UB_13      0.1058939000
_diffrn_orient_matrix_UB_21      0.1391624000
_diffrn_orient_matrix_UB_22      0.0605905000
_diffrn_orient_matrix_UB_23      -0.0015623000
_diffrn_orient_matrix_UB_31      -0.0460964000
_diffrn_orient_matrix_UB_32      0.1636498000
_diffrn_orient_matrix_UB_33      0.0128139000
_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  0.0310
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15516
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.819
_diffrn_reflns_theta_min         3.060
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.693
_exptl_absorpt_correction_T_max  0.991
_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    1.295
_exptl_crystal_description       plate
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 1987 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(9)
_refine_ls_extinction_coef       0.0025(4)
_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   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     350
_refine_ls_number_reflns         5086
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0313
_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)+(0.0430P)²+0.0709P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0775
_refine_ls_wR_factor_ref         0.0791
_reflns_Friedel_coverage         0.824
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.883
_reflns_number_gt                4720
_reflns_number_total             5086
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc05287g2.cif
_cod_data_source_block           acb220008_fa
_cod_depositor_comments          'Adding full bibliography for 1570591.cif.'
_cod_database_code               1570591
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C31 H33 N3 O4'
_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   0.993
_shelx_estimated_absorpt_t_min   0.909
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, 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), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24), C25(H25),
 C27(H27), C28(H28)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_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 1.616
_oxdiff_exptl_absorpt_empirical_full_min 0.538
loop_
_space_group_symop_operation_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 0.76199(16) 0.21400(18) 0.55681(11) 0.0383(4) Uani 1 1 d . . . . .
O2 O 0.53374(13) 0.32280(17) 0.76751(10) 0.0292(3) Uani 1 1 d . . . . .
O3 O 0.27858(15) 0.26975(18) 0.91881(10) 0.0328(3) Uani 1 1 d . . . . .
O4 O 0.33394(14) 0.09647(16) 0.81975(10) 0.0295(3) Uani 1 1 d . . . . .
N1 N 0.74858(16) 0.3594(2) 0.68167(12) 0.0269(4) Uani 1 1 d . . . . .
H1 H 0.710(2) 0.358(3) 0.7252(17) 0.032 Uiso 1 1 d . U . . .
N2 N 0.49621(15) 0.16652(19) 0.64320(11) 0.0261(4) Uani 1 1 d . . . . .
N3 N 0.26615(15) 0.32494(19) 0.76789(11) 0.0244(3) Uani 1 1 d . . . . .
C1 C 0.72314(19) 0.2341(2) 0.62647(14) 0.0269(4) Uani 1 1 d . . . . .
C2 C 0.63670(19) 0.1154(2) 0.66115(14) 0.0269(4) Uani 1 1 d . . . . .
H2 H 0.673711 0.096076 0.728799 0.032 Uiso 1 1 calc R U . . .
C3 C 0.6255(2) -0.0335(3) 0.60756(15) 0.0325(5) Uani 1 1 d . . . . .
H3A H 0.609418 -0.120275 0.645772 0.039 Uiso 1 1 calc R U . . .
H3B H 0.707416 -0.053477 0.586589 0.039 Uiso 1 1 calc R U . . .
C4 C 0.5057(2) -0.0070(3) 0.52528(16) 0.0381(5) Uani 1 1 d . . . . .
H4A H 0.530832 0.055403 0.476981 0.046 Uiso 1 1 calc R U . . .
H4B H 0.467628 -0.104826 0.497702 0.046 Uiso 1 1 calc R U . . .
C5 C 0.4078(2) 0.0778(3) 0.56845(15) 0.0343(5) Uani 1 1 d . . . . .
H5A H 0.349103 0.145500 0.522763 0.041 Uiso 1 1 calc R U . . .
H5B H 0.352058 0.005809 0.593537 0.041 Uiso 1 1 calc R U . . .
C6 C 0.45481(18) 0.2596(2) 0.70255(13) 0.0241(4) Uani 1 1 d . . . . .
C7 C 0.30378(18) 0.2843(2) 0.68343(13) 0.0243(4) Uani 1 1 d . . . . .
H7 H 0.254695 0.190955 0.655084 0.029 Uiso 1 1 calc R U . . .
C8 C 0.2576(2) 0.4233(3) 0.62178(14) 0.0309(5) Uani 1 1 d . . . . .
H8A H 0.311211 0.436134 0.575871 0.037 Uiso 1 1 calc R U . . .
H8B H 0.162141 0.414774 0.588783 0.037 Uiso 1 1 calc R U . . .
C9 C 0.2805(2) 0.5544(2) 0.69055(16) 0.0331(5) Uani 1 1 d . . . . .
H9A H 0.225037 0.643689 0.664858 0.040 Uiso 1 1 calc R U . . .
H9B H 0.375555 0.585297 0.707810 0.040 Uiso 1 1 calc R U . . .
C10 C 0.2384(2) 0.4880(2) 0.77361(16) 0.0308(5) Uani 1 1 d . . . . .
H10A H 0.291460 0.532205 0.832401 0.037 Uiso 1 1 calc R U . . .
H10B H 0.142465 0.506230 0.768567 0.037 Uiso 1 1 calc R U . . .
C11 C 0.29314(19) 0.2331(2) 0.84338(14) 0.0254(4) Uani 1 1 d . . . . .
C12 C 0.3888(2) -0.0211(2) 0.88937(15) 0.0327(5) Uani 1 1 d . . . . .
C13 C 0.4476(3) -0.1323(3) 0.83244(19) 0.0458(6) Uani 1 1 d . . . . .
H13A H 0.378524 -0.163234 0.777664 0.069 Uiso 1 1 calc R U . . .
H13B H 0.481251 -0.222292 0.869946 0.069 Uiso 1 1 calc R U . . .
H13C H 0.521144 -0.083122 0.812922 0.069 Uiso 1 1 calc R U . . .
C14 C 0.2769(3) -0.0930(3) 0.9235(2) 0.0511(7) Uani 1 1 d . . . . .
H14A H 0.231238 -0.014254 0.950634 0.077 Uiso 1 1 calc R U . . .
H14B H 0.313885 -0.170031 0.970548 0.077 Uiso 1 1 calc R U . . .
H14C H 0.213202 -0.141337 0.871506 0.077 Uiso 1 1 calc R U . . .
C15 C 0.4984(3) 0.0442(3) 0.96651(18) 0.0506(7) Uani 1 1 d . . . . .
H15A H 0.559399 0.104417 0.939968 0.076 Uiso 1 1 calc R U . . .
H15B H 0.547707 -0.039092 1.003681 0.076 Uiso 1 1 calc R U . . .
H15C H 0.459007 0.109580 1.005913 0.076 Uiso 1 1 calc R U . . .
C16 C 0.82021(19) 0.4919(2) 0.67134(14) 0.0262(4) Uani 1 1 d . . . . .
C17 C 0.87936(19) 0.5099(3) 0.59722(14) 0.0297(4) Uani 1 1 d . . . . .
H17 H 0.875446 0.429396 0.554071 0.036 Uiso 1 1 calc R U . . .
C18 C 0.9437(2) 0.6450(3) 0.58654(14) 0.0320(5) Uani 1 1 d . . . . .
H18 H 0.983364 0.655040 0.535896 0.038 Uiso 1 1 calc R U . . .
C19 C 0.95169(19) 0.7658(3) 0.64762(14) 0.0291(4) Uani 1 1 d . . . . .
C20 C 1.0122(2) 0.9105(3) 0.63566(15) 0.0333(5) Uani 1 1 d . . . . .
H20 H 1.051074 0.923417 0.584798 0.040 Uiso 1 1 calc R U . . .
C21 C 1.0151(2) 1.0262(3) 0.69396(16) 0.0367(5) Uani 1 1 d . . . . .
H21 H 1.053549 1.120329 0.682628 0.044 Uiso 1 1 calc R U . . .
C22 C 0.96148(19) 1.0122(3) 0.77334(15) 0.0323(5) Uani 1 1 d . . . . .
C23 C 0.9651(2) 1.1310(3) 0.83608(17) 0.0379(5) Uani 1 1 d . . . . .
H23 H 1.002310 1.226255 0.825532 0.046 Uiso 1 1 calc R U . . .
C24 C 0.9155(2) 1.1126(3) 0.91355(18) 0.0405(5) Uani 1 1 d . . . . .
H24 H 0.919906 1.194493 0.955893 0.049 Uiso 1 1 calc R U . . .
C25 C 0.8595(2) 0.9750(3) 0.92919(16) 0.0380(5) Uani 1 1 d . . . . .
H25 H 0.826238 0.962893 0.982638 0.046 Uiso 1 1 calc R U . . .
C26 C 0.8512(2) 0.8539(3) 0.86756(15) 0.0310(5) Uani 1 1 d . . . . .
C27 C 0.7908(2) 0.7109(3) 0.88080(15) 0.0333(5) Uani 1 1 d . . . . .
H27 H 0.757978 0.697061 0.934277 0.040 Uiso 1 1 calc R U . . .
C28 C 0.7796(2) 0.5958(3) 0.81935(14) 0.0310(5) Uani 1 1 d . . . . .
H28 H 0.736712 0.504010 0.829624 0.037 Uiso 1 1 calc R U . . .
C29 C 0.83120(19) 0.6091(2) 0.73836(13) 0.0254(4) Uani 1 1 d . . . . .
C30 C 0.89585(18) 0.7475(2) 0.72519(14) 0.0260(4) Uani 1 1 d . . . . .
C31 C 0.90307(19) 0.8701(2) 0.78881(15) 0.0278(4) Uani 1 1 d . . . . .
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 1 0.0686
1 -1 -1 0.0316
0 1 0 0.0880
0 -1 0 0.0500
-1 0 0 0.0320
0 0 1 0.0055
0 0 -1 0.0075
1 0 -1 0.0271
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
C11 O4 C12 121.98(16) . . ?
C1 N1 H1 113.4(17) . . ?
C1 N1 C16 128.98(18) . . ?
C16 N1 H1 117.4(17) . . ?
C5 N2 C2 111.82(15) . . ?
C6 N2 C2 121.53(15) . . ?
C6 N2 C5 125.20(15) . . ?
C7 N3 C10 112.89(17) . . ?
C11 N3 C7 122.00(16) . . ?
C11 N3 C10 122.31(17) . . ?
O1 C1 N1 125.39(19) . . ?
O1 C1 C2 122.08(18) . . ?
N1 C1 C2 112.54(16) . . ?
N2 C2 C1 111.10(16) . . ?
N2 C2 H2 110.2 . . ?
N2 C2 C3 102.89(16) . . ?
C1 C2 H2 110.2 . . ?
C3 C2 C1 112.19(16) . . ?
C3 C2 H2 110.2 . . ?
C2 C3 H3A 111.1 . . ?
C2 C3 H3B 111.1 . . ?
C2 C3 C4 103.38(17) . . ?
H3A C3 H3B 109.1 . . ?
C4 C3 H3A 111.1 . . ?
C4 C3 H3B 111.1 . . ?
C3 C4 H4A 111.1 . . ?
C3 C4 H4B 111.1 . . ?
H4A C4 H4B 109.1 . . ?
C5 C4 C3 103.08(17) . . ?
C5 C4 H4A 111.1 . . ?
C5 C4 H4B 111.1 . . ?
N2 C5 C4 103.01(16) . . ?
N2 C5 H5A 111.2 . . ?
N2 C5 H5B 111.2 . . ?
C4 C5 H5A 111.2 . . ?
C4 C5 H5B 111.2 . . ?
H5A C5 H5B 109.1 . . ?
O2 C6 N2 122.08(17) . . ?
O2 C6 C7 121.83(17) . . ?
N2 C6 C7 116.08(16) . . ?
N3 C7 C6 110.83(15) . . ?
N3 C7 H7 110.5 . . ?
N3 C7 C8 102.35(16) . . ?
C6 C7 H7 110.5 . . ?
C8 C7 C6 112.04(16) . . ?
C8 C7 H7 110.5 . . ?
C7 C8 H8A 111.2 . . ?
C7 C8 H8B 111.2 . . ?
H8A C8 H8B 109.1 . . ?
C9 C8 C7 103.02(16) . . ?
C9 C8 H8A 111.2 . . ?
C9 C8 H8B 111.2 . . ?
C8 C9 H9A 111.1 . . ?
C8 C9 H9B 111.1 . . ?
C8 C9 C10 103.31(17) . . ?
H9A C9 H9B 109.1 . . ?
C10 C9 H9A 111.1 . . ?
C10 C9 H9B 111.1 . . ?
N3 C10 C9 103.03(17) . . ?
N3 C10 H10A 111.2 . . ?
N3 C10 H10B 111.2 . . ?
C9 C10 H10A 111.2 . . ?
C9 C10 H10B 111.2 . . ?
H10A C10 H10B 109.1 . . ?
O3 C11 O4 126.68(19) . . ?
O3 C11 N3 124.35(18) . . ?
O4 C11 N3 108.94(16) . . ?
O4 C12 C13 101.16(17) . . ?
O4 C12 C14 109.66(17) . . ?
O4 C12 C15 110.76(19) . . ?
C14 C12 C13 111.6(2) . . ?
C15 C12 C13 109.9(2) . . ?
C15 C12 C14 113.1(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 C29 118.23(17) . . ?
C17 C16 N1 121.74(19) . . ?
C17 C16 C29 120.04(18) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.3(2) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 119.0 . . ?
C19 C18 C17 121.92(19) . . ?
C19 C18 H18 119.0 . . ?
C18 C19 C20 123.11(19) . . ?
C18 C19 C30 118.5(2) . . ?
C30 C19 C20 118.4(2) . . ?
C19 C20 H20 119.1 . . ?
C21 C20 C19 121.9(2) . . ?
C21 C20 H20 119.1 . . ?
C20 C21 H21 119.2 . . ?
C20 C21 C22 121.6(2) . . ?
C22 C21 H21 119.2 . . ?
C23 C22 C21 122.6(2) . . ?
C23 C22 C31 119.0(2) . . ?
C31 C22 C21 118.4(2) . . ?
C22 C23 H23 119.4 . . ?
C24 C23 C22 121.3(2) . . ?
C24 C23 H23 119.4 . . ?
C23 C24 H24 120.0 . . ?
C25 C24 C23 120.0(2) . . ?
C25 C24 H24 120.0 . . ?
C24 C25 H25 119.6 . . ?
C24 C25 C26 120.9(2) . . ?
C26 C25 H25 119.6 . . ?
C25 C26 C27 122.1(2) . . ?
C25 C26 C31 119.8(2) . . ?
C31 C26 C27 118.02(19) . . ?
C26 C27 H27 119.1 . . ?
C28 C27 C26 121.79(19) . . ?
C28 C27 H27 119.1 . . ?
C27 C28 H28 119.3 . . ?
C27 C28 C29 121.4(2) . . ?
C29 C28 H28 119.3 . . ?
C16 C29 C28 123.38(18) . . ?
C16 C29 C30 118.59(17) . . ?
C30 C29 C28 118.03(18) . . ?
C29 C30 C19 120.53(19) . . ?
C29 C30 C31 120.04(17) . . ?
C31 C30 C19 119.42(18) . . ?
C26 C31 C22 119.01(19) . . ?
C26 C31 C30 120.64(18) . . ?
C30 C31 C22 120.35(19) . . ?
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 1.217(2) . ?
O2 C6 1.232(2) . ?
O3 C11 1.215(2) . ?
O4 C11 1.347(2) . ?
O4 C12 1.473(2) . ?
N1 H1 0.85(3) . ?
N1 C1 1.359(3) . ?
N1 C16 1.408(3) . ?
N2 C2 1.481(2) . ?
N2 C5 1.475(2) . ?
N2 C6 1.351(2) . ?
N3 C7 1.453(2) . ?
N3 C10 1.466(3) . ?
N3 C11 1.356(3) . ?
C1 C2 1.544(3) . ?
C2 H2 1.0000 . ?
C2 C3 1.521(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.528(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.524(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.533(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.531(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.520(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.528(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C12 C13 1.517(3) . ?
C12 C14 1.515(3) . ?
C12 C15 1.512(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.400(3) . ?
C16 C29 1.419(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.388(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.386(3) . ?
C19 C20 1.447(3) . ?
C19 C30 1.426(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.332(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.433(3) . ?
C22 C23 1.395(3) . ?
C22 C31 1.430(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.386(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.385(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.393(3) . ?
C26 C27 1.437(3) . ?
C26 C31 1.416(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.349(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.443(3) . ?
C29 C30 1.424(3) . ?
C30 C31 1.424(3) . ?
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 -106.0(2) . . . . ?
O1 C1 C2 C3 8.6(3) . . . . ?
O2 C6 C7 N3 -26.4(3) . . . . ?
O2 C6 C7 C8 87.2(2) . . . . ?
N1 C1 C2 N2 73.8(2) . . . . ?
N1 C1 C2 C3 -171.68(16) . . . . ?
N1 C16 C17 C18 176.83(18) . . . . ?
N1 C16 C29 C28 3.8(3) . . . . ?
N1 C16 C29 C30 -175.93(16) . . . . ?
N2 C2 C3 C4 31.9(2) . . . . ?
N2 C6 C7 N3 154.58(17) . . . . ?
N2 C6 C7 C8 -91.8(2) . . . . ?
N3 C7 C8 C9 34.05(18) . . . . ?
C1 N1 C16 C17 -0.8(3) . . . . ?
C1 N1 C16 C29 179.02(18) . . . . ?
C1 C2 C3 C4 -87.6(2) . . . . ?
C2 N2 C5 C4 -12.8(2) . . . . ?
C2 N2 C6 O2 9.9(3) . . . . ?
C2 N2 C6 C7 -171.09(17) . . . . ?
C2 C3 C4 C5 -40.3(2) . . . . ?
C3 C4 C5 N2 32.3(2) . . . . ?
C5 N2 C2 C1 108.22(19) . . . . ?
C5 N2 C2 C3 -12.0(2) . . . . ?
C5 N2 C6 O2 175.0(2) . . . . ?
C5 N2 C6 C7 -6.0(3) . . . . ?
C6 N2 C2 C1 -84.9(2) . . . . ?
C6 N2 C2 C3 154.90(18) . . . . ?
C6 N2 C5 C4 -179.13(19) . . . . ?
C6 C7 C8 C9 -84.72(19) . . . . ?
C7 N3 C10 C9 -7.6(2) . . . . ?
C7 N3 C11 O3 170.63(18) . . . . ?
C7 N3 C11 O4 -11.1(2) . . . . ?
C7 C8 C9 C10 -39.33(19) . . . . ?
C8 C9 C10 N3 28.9(2) . . . . ?
C10 N3 C7 C6 103.05(19) . . . . ?
C10 N3 C7 C8 -16.6(2) . . . . ?
C10 N3 C11 O3 11.0(3) . . . . ?
C10 N3 C11 O4 -170.82(17) . . . . ?
C11 O4 C12 C13 -167.40(18) . . . . ?
C11 O4 C12 C14 74.6(2) . . . . ?
C11 O4 C12 C15 -50.9(3) . . . . ?
C11 N3 C7 C6 -58.4(2) . . . . ?
C11 N3 C7 C8 -178.00(17) . . . . ?
C11 N3 C10 C9 153.73(17) . . . . ?
C12 O4 C11 O3 -10.6(3) . . . . ?
C12 O4 C11 N3 171.19(16) . . . . ?
C16 N1 C1 O1 1.5(3) . . . . ?
C16 N1 C1 C2 -178.26(17) . . . . ?
C16 C17 C18 C19 -0.1(3) . . . . ?
C16 C29 C30 C19 -1.8(3) . . . . ?
C16 C29 C30 C31 177.06(17) . . . . ?
C17 C16 C29 C28 -176.45(19) . . . . ?
C17 C16 C29 C30 3.9(3) . . . . ?
C17 C18 C19 C20 -176.84(18) . . . . ?
C17 C18 C19 C30 2.2(3) . . . . ?
C18 C19 C20 C21 178.0(2) . . . . ?
C18 C19 C30 C29 -1.2(3) . . . . ?
C18 C19 C30 C31 179.96(18) . . . . ?
C19 C20 C21 C22 1.8(3) . . . . ?
C19 C30 C31 C22 2.2(3) . . . . ?
C19 C30 C31 C26 -178.55(18) . . . . ?
C20 C19 C30 C29 177.90(18) . . . . ?
C20 C19 C30 C31 -1.0(3) . . . . ?
C20 C21 C22 C23 179.0(2) . . . . ?
C20 C21 C22 C31 -0.5(3) . . . . ?
C21 C22 C23 C24 -178.3(2) . . . . ?
C21 C22 C31 C26 179.23(18) . . . . ?
C21 C22 C31 C30 -1.5(3) . . . . ?
C22 C23 C24 C25 -0.8(3) . . . . ?
C23 C22 C31 C26 -0.3(3) . . . . ?
C23 C22 C31 C30 178.95(18) . . . . ?
C23 C24 C25 C26 -0.5(3) . . . . ?
C24 C25 C26 C27 -178.5(2) . . . . ?
C24 C25 C26 C31 1.3(3) . . . . ?
C25 C26 C27 C28 178.0(2) . . . . ?
C25 C26 C31 C22 -1.0(3) . . . . ?
C25 C26 C31 C30 179.83(19) . . . . ?
C26 C27 C28 C29 1.8(3) . . . . ?
C27 C26 C31 C22 178.91(19) . . . . ?
C27 C26 C31 C30 -0.3(3) . . . . ?
C27 C28 C29 C16 -179.2(2) . . . . ?
C27 C28 C29 C30 0.5(3) . . . . ?
C28 C29 C30 C19 178.48(18) . . . . ?
C28 C29 C30 C31 -2.7(3) . . . . ?
C29 C16 C17 C18 -3.0(3) . . . . ?
C29 C30 C31 C22 -176.64(17) . . . . ?
C29 C30 C31 C26 2.6(3) . . . . ?
C30 C19 C20 C21 -1.0(3) . . . . ?
C31 C22 C23 C24 1.2(3) . . . . ?
C31 C26 C27 C28 -1.9(3) . . . . ?
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 1.0000 0.0405 -0.0801 0.2226
1.0000 -1.0000 -1.0000 -0.0405 0.0801 -0.2226
0.0000 1.0000 -0.0000 -0.0190 0.0606 0.1636
-0.0000 -1.0000 0.0000 0.0190 -0.0606 -0.1636
-1.0000 -0.0000 -0.0000 -0.0464 -0.1392 0.0461
-0.0000 -0.0000 1.0000 0.1059 -0.0016 0.0128
0.0000 0.0000 -1.0000 -0.1059 0.0016 -0.0128
1.0000 0.0000 -1.0000 -0.0595 0.1407 -0.0589
