#------------------------------------------------------------------------------
#$Date: 2021-12-03 22:52:39 +0200 (Fri, 03 Dec 2021) $
#$Revision: 271045 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/91/4519179.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_4519179
loop_
_publ_author_name
'Kirinde Arachchige, Pandula T.'
'Handunneththige, Suhashini'
'Talipov, Marat R.'
'Kalutharage, Nishantha'
'Yi, Chae S.'
_publ_section_title
;
 Scope and Mechanism of the Redox-Active 1,2-Benzoquinone Enabled
 Ruthenium-Catalyzed Deaminative α-Alkylation of Ketones with Amines
;
_journal_issue                   22
_journal_name_full               'ACS Catalysis'
_journal_page_first              13962
_journal_page_last               13972
_journal_paper_doi               10.1021/acscatal.1c04732
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C20 H23 N O3'
_chemical_formula_sum            'C20 H23 N O3'
_chemical_formula_weight         325.39
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.866(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.16080(10)
_cell_length_b                   12.7726(4)
_cell_length_c                   25.3964(7)
_cell_measurement_reflns_used    6739
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.2950
_cell_measurement_theta_min      4.2670
_cell_volume                     1670.24(8)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3756
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.914
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -14.00  85.00   1.00    9.63    --   10.69  37.00   0.00   99
  2  ω    -20.00  30.00   1.00    9.63    --  -10.77 -99.00 -30.00   50
  3  ω    -52.00  69.00   1.00    9.63    --  -10.77  19.00 -60.00  121
  4  ω    -20.00  25.00   1.00    9.63    --   10.69 -99.00-180.00   45
  5  ω    -35.00  64.00   1.00    9.63    --  -10.77  37.00  60.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0754337000
_diffrn_orient_matrix_UB_12      -0.0348585000
_diffrn_orient_matrix_UB_13      0.0144197000
_diffrn_orient_matrix_UB_21      -0.0595242000
_diffrn_orient_matrix_UB_22      0.0432422000
_diffrn_orient_matrix_UB_23      0.0118916000
_diffrn_orient_matrix_UB_31      -0.0986746000
_diffrn_orient_matrix_UB_32      0.0005424000
_diffrn_orient_matrix_UB_33      -0.0208365000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_Laue_measured_fraction_full 0.914
_diffrn_reflns_Laue_measured_fraction_max 0.914
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            19263
_diffrn_reflns_point_group_measured_fraction_full 0.914
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        29.724
_diffrn_reflns_theta_max         29.724
_diffrn_reflns_theta_min         3.290
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.697
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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    1.294
_exptl_crystal_description       needle
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.803
_exptl_crystal_size_mid          0.238
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         4342
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0513
_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)+(0.0449P)²+1.1276P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1156
_refine_ls_wR_factor_ref         0.1295
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3272
_reflns_number_total             4342
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs1c04732_si_003.cif
_cod_data_source_block           yi4t
_cod_database_code               4519179
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C20 H23 N O3'
_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.
;
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{C19, C19A}
3. Uiso/Uaniso restraints and constraints
Uanis(C20) = Uanis(C20A)
Uanis(O3) = Uanis(O3A)
Uanis(C18B) = Uanis(C18A)
Uanis(C19) = Uanis(C19A)
4. Others
 Sof(C20A)=Sof(H20C)=Sof(H20D)=1-FVAR(1)
 Sof(C20)=Sof(H20A)=Sof(H20B)=FVAR(1)
 Sof(H17C)=Sof(H17D)=Sof(C18B)=Sof(H18C)=Sof(H18D)=1-FVAR(2)
 Sof(H17A)=Sof(H17B)=Sof(C18A)=Sof(H18A)=Sof(H18B)=FVAR(2)
 Sof(O3A)=1-FVAR(3)
 Sof(O3)=FVAR(3)
 Fixed Sof: C19(0.7) H19A(0.7) H19B(0.7) C19A(0.3) H19C(0.3) H19D(0.3)
5.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C17(H17C,H17D), C17(H17A,H17B), C18A(H18A,H18B),
 C18B(H18C,H18D), C19(H19A,H19B), C19A(H19C,H19D), C20(H20A,H20B), C20A(H20C,
 H20D)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C11(H11), C12(H12), C14(H14), C15(H15)
5.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_olex2_date_sample_data_collection 2019-07-24
_olex2_date_sample_submission    2019-07-23
_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 1.126
_oxdiff_exptl_absorpt_empirical_full_min 0.919
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 0.3953(2) 0.66408(8) 0.67224(4) 0.0258(3) Uani 1 1 d . . . . .
O2 O 1.4705(2) 0.24163(9) 0.55119(4) 0.0261(3) Uani 1 1 d . . . . .
O3 O -0.5904(6) 0.41460(18) 0.93197(11) 0.0323(6) Uani 0.682(5) 1 d . . P A 1
O3A O -0.4939(12) 0.4020(4) 0.9481(2) 0.0323(6) Uani 0.318(5) 1 d . . P A 2
N1 N -0.2107(3) 0.46688(10) 0.86092(5) 0.0237(3) Uani 1 1 d . . . . .
C1 C 0.4169(3) 0.57755(11) 0.69258(6) 0.0179(3) Uani 1 1 d . . . . .
C2 C 0.2543(3) 0.54674(11) 0.73616(5) 0.0171(3) Uani 1 1 d . . . . .
C3 C 0.0983(3) 0.62126(12) 0.75884(6) 0.0195(3) Uani 1 1 d . . . . .
H3 H 0.098432 0.691237 0.746156 0.023 Uiso 1 1 calc R . . . .
C4 C -0.0565(3) 0.59568(12) 0.79932(6) 0.0201(3) Uani 1 1 d . . . . .
H4 H -0.158950 0.648459 0.814136 0.024 Uiso 1 1 calc R . . . .
C5 C -0.0647(3) 0.49255(12) 0.81899(5) 0.0180(3) Uani 1 1 d . . . . .
C6 C 0.0857(3) 0.41666(12) 0.79469(6) 0.0199(3) Uani 1 1 d . . . . .
H6 H 0.078985 0.345727 0.805761 0.024 Uiso 1 1 calc R . . . .
C7 C 0.2431(3) 0.44425(12) 0.75491(6) 0.0188(3) Uani 1 1 d . . . . .
H7 H 0.346430 0.391941 0.739951 0.023 Uiso 1 1 calc R . . . .
C8 C 0.6074(3) 0.49781(11) 0.67409(6) 0.0176(3) Uani 1 1 d . . . . .
H8A H 0.509888 0.435992 0.660023 0.021 Uiso 1 1 calc R . . . .
H8B H 0.721543 0.474443 0.704743 0.021 Uiso 1 1 calc R . . . .
C9 C 0.7754(3) 0.53942(11) 0.63178(6) 0.0180(3) Uani 1 1 d . . . . .
H9A H 0.660506 0.566157 0.601979 0.022 Uiso 1 1 calc R . . . .
H9B H 0.878670 0.599181 0.646516 0.022 Uiso 1 1 calc R . . . .
C10 C 0.9589(3) 0.45931(11) 0.61079(5) 0.0171(3) Uani 1 1 d . . . . .
C11 C 0.9956(3) 0.35904(11) 0.63188(6) 0.0190(3) Uani 1 1 d . . . . .
H11 H 0.899323 0.338214 0.660699 0.023 Uiso 1 1 calc R . . . .
C12 C 1.1693(3) 0.28912(12) 0.61180(6) 0.0204(3) Uani 1 1 d . . . . .
H12 H 1.192716 0.221839 0.627341 0.024 Uiso 1 1 calc R . . . .
C13 C 1.3094(3) 0.31692(12) 0.56901(6) 0.0205(3) Uani 1 1 d . . . . .
C14 C 1.2761(3) 0.41610(12) 0.54724(6) 0.0210(3) Uani 1 1 d . . . . .
H14 H 1.370341 0.436299 0.518030 0.025 Uiso 1 1 calc R . . . .
C15 C 1.1038(3) 0.48577(12) 0.56845(6) 0.0200(3) Uani 1 1 d . . . . .
H15 H 1.084446 0.553741 0.553516 0.024 Uiso 1 1 calc R . . . .
C16 C 1.6328(3) 0.27095(15) 0.51007(6) 0.0295(4) Uani 1 1 d . . . . .
H16A H 1.524117 0.292146 0.478751 0.044 Uiso 1 1 calc GR . . . .
H16B H 1.740997 0.211238 0.501255 0.044 Uiso 1 1 calc GR . . . .
H16C H 1.744365 0.329533 0.522057 0.044 Uiso 1 1 calc GR . . . .
C17 C -0.2648(4) 0.35822(13) 0.87114(7) 0.0314(4) Uani 1 1 d . . . . .
H17C H -0.100025 0.324928 0.884498 0.038 Uiso 0.370(10) 1 calc R . P B 2
H17D H -0.317300 0.324730 0.836918 0.038 Uiso 0.370(10) 1 calc R . P B 2
H17A H -0.102441 0.317204 0.870133 0.038 Uiso 0.630(10) 1 calc R . P B 1
H17B H -0.389624 0.331234 0.843071 0.038 Uiso 0.630(10) 1 calc R . P B 1
C18A C -0.3761(12) 0.3433(4) 0.9242(2) 0.0360(11) Uani 0.630(10) 1 d . . P A 1
H18A H -0.437885 0.270306 0.927015 0.043 Uiso 0.630(10) 1 calc R . P B 1
H18B H -0.237370 0.354784 0.952418 0.043 Uiso 0.630(10) 1 calc R . P B 1
C18B C -0.463(2) 0.3323(8) 0.9082(4) 0.0360(11) Uani 0.370(10) 1 d . . P A 2
H18C H -0.632042 0.324781 0.887638 0.043 Uiso 0.370(10) 1 calc R . P B 2
H18D H -0.419152 0.263285 0.924084 0.043 Uiso 0.370(10) 1 calc R . P B 2
C19 C -0.4936(4) 0.51380(14) 0.93118(7) 0.0320(4) Uani 0.7 1 d . . P A 1
H19A H -0.354077 0.520330 0.959716 0.038 Uiso 0.7 1 calc R . P A 1
H19B H -0.633385 0.563236 0.939147 0.038 Uiso 0.7 1 calc R . P A 1
C19A C -0.4936(4) 0.51380(14) 0.93118(7) 0.0320(4) Uani 0.3 1 d . . P A 2
H19C H -0.654585 0.529213 0.909130 0.038 Uiso 0.3 1 calc R . P A 2
H19D H -0.488896 0.559819 0.962594 0.038 Uiso 0.3 1 calc R . P A 2
C20 C -0.3853(4) 0.54654(17) 0.87963(9) 0.0208(5) Uani 0.728(3) 1 d . . P A 1
H20A H -0.530201 0.558010 0.852683 0.025 Uiso 0.728(3) 1 calc R . P A 1
H20B H -0.289963 0.613420 0.884790 0.025 Uiso 0.728(3) 1 calc R . P A 1
C20A C -0.2688(12) 0.5347(5) 0.9012(2) 0.0208(5) Uani 0.272(3) 1 d . . P A 2
H20C H -0.291301 0.605417 0.885613 0.025 Uiso 0.272(3) 1 calc R . P A 2
H20D H -0.114701 0.537722 0.926573 0.025 Uiso 0.272(3) 1 calc R . P A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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 -1 36 0.1039
0 1 -36 0.0789
6 1 21 0.2534
-6 -1 -21 0.2534
0 -16 16 0.0901
0 16 -16 0.0901
0 -16 -15 0.1081
0 16 15 0.1081
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
C13 O2 C16 117.12(13) . . ?
C19 O3 C18A 107.2(3) . . ?
C18B O3A C19A 114.0(6) . . ?
C5 N1 C17 119.22(13) . . ?
C5 N1 C20 117.72(14) . . ?
C5 N1 C20A 125.1(3) . . ?
C17 N1 C20 118.73(14) . . ?
C20A N1 C17 114.4(3) . . ?
O1 C1 C2 120.94(13) . . ?
O1 C1 C8 121.38(13) . . ?
C2 C1 C8 117.67(12) . . ?
C3 C2 C1 119.80(13) . . ?
C7 C2 C1 122.75(13) . . ?
C7 C2 C3 117.42(13) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.58(14) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.10(13) . . ?
C5 C4 H4 119.4 . . ?
N1 C5 C4 121.63(13) . . ?
N1 C5 C6 121.20(13) . . ?
C6 C5 C4 117.17(13) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.80(14) . . ?
C7 C6 H6 119.6 . . ?
C2 C7 H7 119.1 . . ?
C6 C7 C2 121.86(13) . . ?
C6 C7 H7 119.1 . . ?
C1 C8 H8A 108.9 . . ?
C1 C8 H8B 108.9 . . ?
C1 C8 C9 113.41(12) . . ?
H8A C8 H8B 107.7 . . ?
C9 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C8 C9 H9A 108.7 . . ?
C8 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C10 C9 C8 114.32(12) . . ?
C10 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
C11 C10 C9 123.81(13) . . ?
C15 C10 C9 119.26(13) . . ?
C15 C10 C11 116.92(13) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 C10 121.61(13) . . ?
C12 C11 H11 119.2 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.38(14) . . ?
C13 C12 H12 119.8 . . ?
O2 C13 C12 116.00(14) . . ?
O2 C13 C14 124.84(13) . . ?
C14 C13 C12 119.15(14) . . ?
C13 C14 H14 120.2 . . ?
C13 C14 C15 119.64(14) . . ?
C15 C14 H14 120.2 . . ?
C10 C15 H15 118.9 . . ?
C14 C15 C10 122.28(14) . . ?
C14 C15 H15 118.9 . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 H17C 107.6 . . ?
N1 C17 H17D 107.6 . . ?
N1 C17 H17A 109.3 . . ?
N1 C17 H17B 109.3 . . ?
N1 C17 C18A 111.8(3) . . ?
N1 C17 C18B 118.8(4) . . ?
H17C C17 H17D 107.0 . . ?
H17A C17 H17B 107.9 . . ?
C18A C17 H17A 109.3 . . ?
C18A C17 H17B 109.3 . . ?
C18B C17 H17C 107.6 . . ?
C18B C17 H17D 107.6 . . ?
O3 C18A C17 112.4(4) . . ?
O3 C18A H18A 109.1 . . ?
O3 C18A H18B 109.1 . . ?
C17 C18A H18A 109.1 . . ?
C17 C18A H18B 109.1 . . ?
H18A C18A H18B 107.9 . . ?
O3A C18B C17 116.6(8) . . ?
O3A C18B H18C 108.1 . . ?
O3A C18B H18D 108.1 . . ?
C17 C18B H18C 108.1 . . ?
C17 C18B H18D 108.1 . . ?
H18C C18B H18D 107.3 . . ?
O3 C19 H19A 108.5 . . ?
O3 C19 H19B 108.5 . . ?
O3 C19 C20 115.22(18) . . ?
H19A C19 H19B 107.5 . . ?
C20 C19 H19A 108.5 . . ?
C20 C19 H19B 108.5 . . ?
O3A C19A H19C 109.6 . . ?
O3A C19A H19D 109.6 . . ?
H19C C19A H19D 108.2 . . ?
C20A C19A O3A 110.1(3) . . ?
C20A C19A H19C 109.6 . . ?
C20A C19A H19D 109.6 . . ?
N1 C20 C19 111.12(16) . . ?
N1 C20 H20A 109.4 . . ?
N1 C20 H20B 109.4 . . ?
C19 C20 H20A 109.4 . . ?
C19 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
N1 C20A C19A 119.4(4) . . ?
N1 C20A H20C 107.5 . . ?
N1 C20A H20D 107.5 . . ?
C19A C20A H20C 107.5 . . ?
C19A C20A H20D 107.5 . . ?
H20C C20A H20D 107.0 . . ?
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 1.2218(18) . ?
O2 C13 1.3683(17) . ?
O2 C16 1.4318(19) . ?
O3 C18A 1.456(6) . ?
O3 C19 1.363(3) . ?
O3A C18B 1.368(12) . ?
O3A C19A 1.491(6) . ?
N1 C5 1.3847(18) . ?
N1 C17 1.443(2) . ?
N1 C20 1.460(2) . ?
N1 C20A 1.388(6) . ?
C1 C2 1.4863(19) . ?
C1 C8 1.512(2) . ?
C2 C3 1.396(2) . ?
C2 C7 1.396(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.410(2) . ?
C5 C6 1.410(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.384(2) . ?
C7 H7 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.5212(19) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5153(19) . ?
C10 C11 1.396(2) . ?
C10 C15 1.392(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.387(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.391(2) . ?
C13 C14 1.388(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.392(2) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17C 0.9900 . ?
C17 H17D 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18A 1.511(5) . ?
C17 C18B 1.473(9) . ?
C18A H18A 0.9900 . ?
C18A H18B 0.9900 . ?
C18B H18C 0.9900 . ?
C18B H18D 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.516(3) . ?
C19A H19C 0.9900 . ?
C19A H19D 0.9900 . ?
C19A C20A 1.455(6) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20A H20C 0.9900 . ?
C20A H20D 0.9900 . ?
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 -8.2(2) . . . . ?
O1 C1 C2 C7 169.78(14) . . . . ?
O1 C1 C8 C9 4.1(2) . . . . ?
O2 C13 C14 C15 179.23(13) . . . . ?
O3 C19 C20 N1 -48.3(3) . . . . ?
O3A C19A C20A N1 47.9(6) . . . . ?
N1 C5 C6 C7 -176.10(14) . . . . ?
N1 C17 C18A O3 49.3(6) . . . . ?
N1 C17 C18B O3A -30.5(10) . . . . ?
C1 C2 C3 C4 179.76(13) . . . . ?
C1 C2 C7 C6 -178.44(13) . . . . ?
C1 C8 C9 C10 -177.23(11) . . . . ?
C2 C1 C8 C9 -176.46(12) . . . . ?
C2 C3 C4 C5 -0.7(2) . . . . ?
C3 C2 C7 C6 -0.5(2) . . . . ?
C3 C4 C5 N1 177.33(14) . . . . ?
C3 C4 C5 C6 -1.6(2) . . . . ?
C4 C5 C6 C7 2.9(2) . . . . ?
C5 N1 C17 C18A 168.2(3) . . . . ?
C5 N1 C17 C18B -167.3(5) . . . . ?
C5 N1 C20 C19 -169.87(15) . . . . ?
C5 N1 C20A C19A 157.4(3) . . . . ?
C5 C6 C7 C2 -1.9(2) . . . . ?
C7 C2 C3 C4 1.7(2) . . . . ?
C8 C1 C2 C3 172.40(13) . . . . ?
C8 C1 C2 C7 -9.7(2) . . . . ?
C8 C9 C10 C11 -6.9(2) . . . . ?
C8 C9 C10 C15 173.88(12) . . . . ?
C9 C10 C11 C12 -178.90(13) . . . . ?
C9 C10 C15 C14 179.94(13) . . . . ?
C10 C11 C12 C13 -1.2(2) . . . . ?
C11 C10 C15 C14 0.7(2) . . . . ?
C11 C12 C13 O2 -178.32(13) . . . . ?
C11 C12 C13 C14 1.0(2) . . . . ?
C12 C13 C14 C15 0.0(2) . . . . ?
C13 C14 C15 C10 -0.8(2) . . . . ?
C15 C10 C11 C12 0.3(2) . . . . ?
C16 O2 C13 C12 -174.99(13) . . . . ?
C16 O2 C13 C14 5.7(2) . . . . ?
C17 N1 C5 C4 164.76(15) . . . . ?
C17 N1 C5 C6 -16.3(2) . . . . ?
C17 N1 C20 C19 33.7(2) . . . . ?
C17 N1 C20A C19A -35.7(6) . . . . ?
C18A O3 C19 C20 62.5(4) . . . . ?
C18B O3A C19A C20A -50.5(8) . . . . ?
C19 O3 C18A C17 -62.7(5) . . . . ?
C19A O3A C18B C17 43.1(10) . . . . ?
C20 N1 C5 C4 8.4(2) . . . . ?
C20 N1 C5 C6 -172.65(15) . . . . ?
C20 N1 C17 C18A -35.7(4) . . . . ?
C20A N1 C5 C4 -28.9(4) . . . . ?
C20A N1 C5 C6 150.0(4) . . . . ?
C20A N1 C17 C18B 24.9(6) . . . . ?
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
-0.0000 -1.0000 36.0002 0.5540 0.3849 -0.7507
0.0000 1.0000 -36.0002 -0.5540 -0.3849 0.7507
6.0000 1.0000 21.0000 -0.1846 -0.0642 -1.0291
-6.0000 -1.0000 -21.0000 0.1846 0.0642 1.0291
0.0000 -15.9999 15.9999 0.7884 -0.5016 -0.3421
-0.0000 15.9999 -15.9999 -0.7884 0.5016 0.3421
0.0000 -15.9999 -15.0002 0.3414 -0.8702 0.3039
-0.0000 15.9999 15.0002 -0.3414 0.8702 -0.3039
