#------------------------------------------------------------------------------
#$Date: 2020-09-06 13:22:10 +0300 (Sun, 06 Sep 2020) $
#$Revision: 256178 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/76/7157663.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_7157663
loop_
_publ_author_name
'Greve, Eric'
'Lindeman, Sergey V.'
'Scartelli, Christina'
'Lin, Lin'
'Flaumenhaft, Robert'
'Dockendorff, Chris'
_publ_section_title
;
 Route exploration and synthesis of the reported pyridone-based PDI
 inhibitor STK076545.
;
_journal_issue                   34
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6665
_journal_page_last               6681
_journal_paper_doi               10.1039/d0ob01205j
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C20 H25 N3 O3'
_chemical_formula_sum            'C20 H25 N3 O3'
_chemical_formula_weight         355.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-12-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-05-14 deposited with the CCDC.	2020-08-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.379(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.9620(3)
_cell_length_b                   8.28868(13)
_cell_length_c                   17.5984(3)
_cell_measurement_reflns_used    8540
_cell_measurement_temperature    101(2)
_cell_measurement_theta_max      70.4890
_cell_measurement_theta_min      5.1810
_cell_volume                     1883.22(7)
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      101(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3756
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -117.00 -18.00   0.50    1.00    --  -42.46 -37.00   0.00  198
  2  ω    -92.00  -2.00   0.50    1.00    --  -42.46 125.00-180.00  180
  3  ω   -117.00 -18.00   0.50    1.00    --  -42.46 -37.00  90.00  198
  4  ω     22.00  97.00   0.50    1.00    --   42.46-123.00 -74.00  150
  5  ω     74.00 173.00   0.50    4.00    --  100.00  45.00-150.00  198
  6  ω     24.00 128.00   0.50    4.00    --  100.00 -30.00  90.00  208
  7  ω     27.00 126.00   0.50    4.00    --  100.00 -45.00 -60.00  198
  8  ω     94.00 173.00   0.50    4.00    --  100.00 125.00 -60.00  158
  9  ω     17.00 110.00   0.50    4.00    --  100.00 -94.00   0.00  186
 10  ω     17.00 110.00   0.50    4.00    --  100.00 -94.00 -90.00  186
 11  ω     71.00 172.00   0.50    4.00    --  100.00  61.00  90.00  202
 12  ω    -92.00  -2.00   0.50    1.00    --  -42.46 125.00  60.00  180
 13  ω   -115.00 -14.00   0.50    1.00    --  -42.46 -57.00 -90.00  202
 14  ω   -119.00 -10.00   0.50    1.00    --  -42.46 -77.00-150.00  218
 15  ω     71.00  98.00   0.50    4.00    --  100.00  61.00 150.00   54
 16  ω     74.00 173.00   0.50    4.00    --  100.00  45.00  30.00  198
 17  ω     74.00 173.00   0.50    4.00    --  100.00  45.00 -90.00  198
;
_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      0.0195464000
_diffrn_orient_matrix_UB_12      0.1522267000
_diffrn_orient_matrix_UB_13      -0.0422453000
_diffrn_orient_matrix_UB_21      0.0449728000
_diffrn_orient_matrix_UB_22      -0.1054571000
_diffrn_orient_matrix_UB_23      -0.0505223000
_diffrn_orient_matrix_UB_31      -0.1087757000
_diffrn_orient_matrix_UB_32      -0.0161763000
_diffrn_orient_matrix_UB_33      -0.0679837000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17568
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        70.471
_diffrn_reflns_theta_max         70.471
_diffrn_reflns_theta_min         3.423
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.689
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.414
_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    1.254
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.485
_exptl_crystal_size_mid          0.258
_exptl_crystal_size_min          0.175
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         3541
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0479
_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)+(0.0684P)²+0.7578P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1307
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3156
_reflns_number_total             3541
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob01205j2.cif
_cod_data_source_block           dock1o
_cod_depositor_comments
'Adding full bibliography for 7157660--7157663.cif.'
_cod_database_code               7157663
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C20 H25 N3 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 99.92
_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 C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C5, C6, C7, C8, C9
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C5A, C6A, C7A, C8A, C9A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C5) = Uanis(C5A)
4. Others
 Fixed Sof: N3(0.5) N3A(0.5) C5(0.5) H5(0.5) C5A(0.5) H5A(0.5) C6(0.5) H6(0.5)
 C6A(0.5) H6A(0.5) C7(0.5) H7(0.5) C7A(0.5) H7A(0.5) C8(0.5) H8(0.5) C8A(0.5)
 H8A(0.5) C9(0.5) H9(0.5) C9A(0.5) H9A(0.5) H15A(0.5) H15B(0.5) H15C(0.5)
 H15D(0.5) C16(0.5) H16A(0.5) H16B(0.5) C16A(0.5) H16C(0.5) H16D(0.5) C17(0.5)
 H17A(0.5) H17B(0.5) C17A(0.5) H17C(0.5) H17D(0.5) C18(0.5) H18A(0.5) H18B(0.5)
 H18C(0.5) C18A(0.5) H18D(0.5) H18E(0.5) H18F(0.5) C19(0.5) H19A(0.5) H19B(0.5)
 C19A(0.5) H19C(0.5) H19D(0.5) C20(0.5) H20A(0.5) H20B(0.5) H20C(0.5) C20A(0.5)
 H20D(0.5) H20E(0.5) H20F(0.5)
5.a Ternary CH refined with riding coordinates:
 C1(H1)
5.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C15(H15C,H15D), C16(H16A,H16B), C16A(H16C,H16D), C17(H17A,
 H17B), C17A(H17C,H17D), C19(H19A,H19B), C19A(H19C,H19D)
5.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C5A(H5A), C6(H6), C6A(H6A), C7(H7), C7A(H7A), C8(H8), C8A(H8A),
 C9(H9), C9A(H9A), C11(H11), C12(H12), C13(H13), C14(H14)
5.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C18A(H18D,H18E,H18F), C20(H20A,H20B,H20C), C20A(H20D,
 H20E,H20F)
;
_olex2_date_sample_data_collection 2019-12-11
_olex2_date_sample_submission    2019-12-11
_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 3.608
_oxdiff_exptl_absorpt_empirical_full_min 0.763
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.28839(10) -0.17178(18) 0.26465(8) 0.0582(4) Uani 1 1 d . . . . .
O2 O 0.25205(7) 0.24134(12) 0.27290(6) 0.0329(3) Uani 1 1 d . . . . .
O3 O 0.49372(7) -0.17948(11) 0.45440(6) 0.0290(2) Uani 1 1 d . . . . .
N1 N 0.45112(9) 0.00783(16) 0.35212(8) 0.0341(3) Uani 1 1 d . . . . .
N2 N 0.35913(10) 0.31702(14) 0.40138(8) 0.0335(3) Uani 1 1 d . . . . .
H2 H 0.4053(15) 0.283(2) 0.4489(12) 0.041(5) Uiso 1 1 d . . . . .
N3 N 0.24388(19) 0.4419(3) 0.48666(17) 0.0222(6) Uiso 0.5 1 d . . P A 1
N3A N 0.2538(2) 0.4771(3) 0.50905(18) 0.0251(6) Uiso 0.5 1 d . . P B 2
C1 C 0.35419(10) 0.03569(16) 0.36423(8) 0.0262(3) Uani 1 1 d . . . . .
H1 H 0.366944 0.017106 0.423445 0.031 Uiso 1 1 calc R . . . .
C2 C 0.27115(11) -0.08289(17) 0.31213(9) 0.0309(3) Uani 1 1 d . . . . .
C3 C 0.31638(10) 0.21051(17) 0.34183(9) 0.0276(3) Uani 1 1 d . . . . .
C4 C 0.17114(11) -0.08781(17) 0.32365(9) 0.0320(3) Uani 1 1 d . . . . .
C5 C 0.1527(10) 0.0171(11) 0.3801(9) 0.0345(13) Uani 0.5 1 d . U P C 1
H5 H 0.206161 0.089486 0.410897 0.041 Uiso 0.5 1 calc R . P C 1
C5A C 0.1563(10) -0.0265(11) 0.3897(9) 0.0345(13) Uani 0.5 1 d . U P C 2
H5A H 0.208328 0.034169 0.430727 0.041 Uiso 0.5 1 calc R . P C 2
C6 C 0.0594(4) 0.0195(6) 0.3929(3) 0.0429(11) Uani 0.5 1 d . U P C 1
H6 H 0.051594 0.088051 0.433411 0.052 Uiso 0.5 1 calc R . P C 1
C6A C 0.0604(4) -0.0573(6) 0.3940(4) 0.0523(12) Uani 0.5 1 d . U P C 2
H6A H 0.046197 -0.015680 0.438958 0.063 Uiso 0.5 1 calc R . P C 2
C7 C -0.0206(5) -0.0788(7) 0.3459(5) 0.0449(14) Uani 0.5 1 d . U P C 1
H7 H -0.085032 -0.075394 0.352402 0.054 Uiso 0.5 1 calc R . P C 1
C7A C -0.0142(5) -0.1464(9) 0.3349(6) 0.0515(16) Uani 0.5 1 d . U P C 2
H7A H -0.079103 -0.164635 0.339196 0.062 Uiso 0.5 1 calc R . P C 2
C8 C -0.0076(9) -0.1816(16) 0.2897(7) 0.043(2) Uani 0.5 1 d . U P C 1
H8 H -0.060870 -0.253654 0.258418 0.052 Uiso 0.5 1 calc R . P C 1
C8A C 0.0045(8) -0.2094(17) 0.2694(7) 0.044(2) Uani 0.5 1 d . U P C 2
H8A H -0.049132 -0.267823 0.228529 0.053 Uiso 0.5 1 calc R . P C 2
C9 C 0.0880(11) -0.1761(17) 0.2803(6) 0.0357(18) Uani 0.5 1 d . U P C 1
H9 H 0.094173 -0.242545 0.238381 0.043 Uiso 0.5 1 calc R . P C 1
C9A C 0.0962(10) -0.1911(16) 0.2612(7) 0.0340(16) Uani 0.5 1 d . U P C 2
H9A H 0.111173 -0.241129 0.218402 0.041 Uiso 0.5 1 calc R . P C 2
C10 C 0.51873(10) -0.10596(17) 0.40302(9) 0.0290(3) Uani 1 1 d . . . . .
C11 C 0.61373(11) -0.12785(19) 0.39058(10) 0.0353(4) Uani 1 1 d . . . . .
H11 H 0.664890 -0.199006 0.425582 0.042 Uiso 1 1 calc R . . . .
C12 C 0.63194(13) -0.0490(2) 0.32985(12) 0.0465(4) Uani 1 1 d . . . . .
H12 H 0.695649 -0.064978 0.323158 0.056 Uiso 1 1 calc R . . . .
C13 C 0.55708(16) 0.0566(3) 0.27654(15) 0.0639(7) Uani 1 1 d . . . . .
H13 H 0.568650 0.108946 0.232776 0.077 Uiso 1 1 calc R . . . .
C14 C 0.46877(15) 0.0814(3) 0.28907(13) 0.0562(6) Uani 1 1 d . . . . .
H14 H 0.417639 0.151652 0.253301 0.067 Uiso 1 1 calc R . . . .
C15 C 0.32770(12) 0.48630(17) 0.39201(9) 0.0336(3) Uani 1 1 d . . . . .
H15A H 0.382486 0.553342 0.432060 0.040 Uiso 0.5 1 calc R . P D 1
H15B H 0.316931 0.524073 0.335983 0.040 Uiso 0.5 1 calc R . P D 1
H15C H 0.259810 0.495498 0.345709 0.040 Uiso 0.5 1 calc R . P E 2
H15D H 0.378544 0.549012 0.377361 0.040 Uiso 0.5 1 calc R . P E 2
C16 C 0.2337(2) 0.5012(3) 0.40583(15) 0.0235(5) Uani 0.5 1 d . . P A 1
H16A H 0.178301 0.439947 0.362997 0.028 Uiso 0.5 1 calc R . P A 1
H16B H 0.212685 0.616094 0.400773 0.028 Uiso 0.5 1 calc R . P A 1
C16A C 0.3181(2) 0.5687(3) 0.47510(17) 0.0299(6) Uani 0.5 1 d . . P B 2
H16C H 0.388450 0.579663 0.518079 0.036 Uiso 0.5 1 calc R . P B 2
H16D H 0.288753 0.678458 0.460968 0.036 Uiso 0.5 1 calc R . P B 2
C17 C 0.3296(2) 0.5209(3) 0.55437(16) 0.0249(5) Uani 0.5 1 d . . P A 1
H17A H 0.395611 0.488122 0.550231 0.030 Uiso 0.5 1 calc R . P A 1
H17B H 0.329994 0.478001 0.607008 0.030 Uiso 0.5 1 calc R . P A 1
C17A C 0.2522(2) 0.5579(4) 0.58320(17) 0.0311(6) Uani 0.5 1 d . . P B 2
H17C H 0.324435 0.584850 0.619055 0.037 Uiso 0.5 1 calc R . P B 2
H17D H 0.226167 0.480009 0.613437 0.037 Uiso 0.5 1 calc R . P B 2
C18 C 0.3277(2) 0.7044(4) 0.55836(19) 0.0345(7) Uani 0.5 1 d . . P A 1
H18A H 0.334680 0.749762 0.509273 0.052 Uiso 0.5 1 calc GR . P A 1
H18B H 0.385334 0.741752 0.607485 0.052 Uiso 0.5 1 calc GR . P A 1
H18C H 0.262044 0.739811 0.560872 0.052 Uiso 0.5 1 calc GR . P A 1
C18A C 0.1872(3) 0.7119(4) 0.56944(19) 0.0387(7) Uani 0.5 1 d . . P B 2
H18D H 0.114293 0.686110 0.537759 0.058 Uiso 0.5 1 calc GR . P B 2
H18E H 0.211370 0.790409 0.539076 0.058 Uiso 0.5 1 calc GR . P B 2
H18F H 0.194308 0.757647 0.622661 0.058 Uiso 0.5 1 calc GR . P B 2
C19 C 0.1437(2) 0.4586(4) 0.4962(2) 0.0302(6) Uani 0.5 1 d . . P A 1
H19A H 0.088209 0.414705 0.446549 0.036 Uiso 0.5 1 calc R . P A 1
H19B H 0.129302 0.574677 0.499781 0.036 Uiso 0.5 1 calc R . P A 1
C19A C 0.1497(2) 0.4435(4) 0.4486(2) 0.0311(6) Uani 0.5 1 d . . P B 2
H19C H 0.155204 0.386763 0.400923 0.037 Uiso 0.5 1 calc R . P B 2
H19D H 0.112984 0.546708 0.428695 0.037 Uiso 0.5 1 calc R . P B 2
C20 C 0.1401(3) 0.3740(5) 0.5706(2) 0.0470(9) Uani 0.5 1 d . . P A 1
H20A H 0.069168 0.376420 0.568912 0.070 Uiso 0.5 1 calc GR . P A 1
H20B H 0.186483 0.428696 0.620353 0.070 Uiso 0.5 1 calc GR . P A 1
H20C H 0.162332 0.261761 0.570943 0.070 Uiso 0.5 1 calc GR . P A 1
C20A C 0.0873(3) 0.3411(4) 0.4845(2) 0.0409(7) Uani 0.5 1 d . . P B 2
H20D H 0.023874 0.303931 0.440190 0.061 Uiso 0.5 1 calc GR . P B 2
H20E H 0.069106 0.405396 0.523742 0.061 Uiso 0.5 1 calc GR . P B 2
H20F H 0.128561 0.247611 0.512647 0.061 Uiso 0.5 1 calc GR . P B 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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
2 -1 -11 0.1112
-6 1 10 0.1141
-8 1 1 0.0717
8 -1 2 0.0805
-3 -5 4 0.1704
-5 4 -2 0.1381
3 0 -11 0.0859
6 1 4 0.1067
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
C10 N1 C1 116.76(11) . . ?
C14 N1 C1 120.59(12) . . ?
C14 N1 C10 122.43(13) . . ?
C3 N2 H2 119.0(12) . . ?
C3 N2 C15 121.67(12) . . ?
C15 N2 H2 119.3(13) . . ?
C16 N3 C17 112.6(2) . . ?
C16 N3 C19 109.5(2) . . ?
C19 N3 C17 112.2(3) . . ?
C16A N3A C17A 110.1(3) . . ?
C16A N3A C19A 113.3(3) . . ?
C19A N3A C17A 112.6(3) . . ?
N1 C1 H1 108.6 . . ?
N1 C1 C2 110.02(12) . . ?
N1 C1 C3 110.86(11) . . ?
C2 C1 H1 108.6 . . ?
C2 C1 C3 110.06(11) . . ?
C3 C1 H1 108.6 . . ?
O1 C2 C1 120.16(14) . . ?
O1 C2 C4 121.60(14) . . ?
C4 C2 C1 118.22(12) . . ?
O2 C3 N2 125.52(13) . . ?
O2 C3 C1 119.86(13) . . ?
N2 C3 C1 114.62(12) . . ?
C5 C4 C2 120.7(5) . . ?
C5A C4 C2 124.4(6) . . ?
C5A C4 C9A 124.2(7) . . ?
C9 C4 C2 126.4(4) . . ?
C9 C4 C5 112.7(7) . . ?
C9A C4 C2 110.6(4) . . ?
C4 C5 H5 118.4 . . ?
C6 C5 C4 123.3(10) . . ?
C6 C5 H5 118.4 . . ?
C4 C5A H5A 121.9 . . ?
C4 C5A C6A 116.2(10) . . ?
C6A C5A H5A 121.9 . . ?
C5 C6 H6 120.5 . . ?
C7 C6 C5 119.0(8) . . ?
C7 C6 H6 120.5 . . ?
C5A C6A H6A 119.2 . . ?
C7A C6A C5A 121.6(8) . . ?
C7A C6A H6A 119.2 . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.2(7) . . ?
C8 C7 H7 119.9 . . ?
C6A C7A H7A 119.7 . . ?
C6A C7A C8A 120.5(8) . . ?
C8A C7A H7A 119.7 . . ?
C7 C8 H8 121.4 . . ?
C7 C8 C9 117.3(9) . . ?
C9 C8 H8 121.4 . . ?
C7A C8A H8A 118.8 . . ?
C9A C8A C7A 122.4(9) . . ?
C9A C8A H8A 118.8 . . ?
C4 C9 C8 127.3(7) . . ?
C4 C9 H9 116.4 . . ?
C8 C9 H9 116.4 . . ?
C4 C9A H9A 122.6 . . ?
C8A C9A C4 114.8(6) . . ?
C8A C9A H9A 122.6 . . ?
O3 C10 N1 119.31(12) . . ?
O3 C10 C11 125.42(13) . . ?
N1 C10 C11 115.27(12) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.35(14) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.59(15) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 120.7 . . ?
C14 C13 C12 118.55(16) . . ?
C14 C13 H13 120.7 . . ?
N1 C14 H14 119.2 . . ?
C13 C14 N1 121.51(15) . . ?
C13 C14 H14 119.2 . . ?
N2 C15 H15A 110.0 . . ?
N2 C15 H15B 110.0 . . ?
N2 C15 H15C 108.6 . . ?
N2 C15 H15D 108.6 . . ?
N2 C15 C16A 114.59(15) . . ?
H15A C15 H15B 108.3 . . ?
H15C C15 H15D 107.6 . . ?
C16 C15 N2 108.67(15) . . ?
C16 C15 H15A 110.0 . . ?
C16 C15 H15B 110.0 . . ?
C16A C15 H15C 108.6 . . ?
C16A C15 H15D 108.6 . . ?
N3 C16 H16A 109.1 . . ?
N3 C16 H16B 109.1 . . ?
C15 C16 N3 112.4(2) . . ?
C15 C16 H16A 109.1 . . ?
C15 C16 H16B 109.1 . . ?
H16A C16 H16B 107.9 . . ?
N3A C16A C15 114.4(2) . . ?
N3A C16A H16C 108.7 . . ?
N3A C16A H16D 108.7 . . ?
C15 C16A H16C 108.7 . . ?
C15 C16A H16D 108.7 . . ?
H16C C16A H16D 107.6 . . ?
N3 C17 H17A 108.0 . . ?
N3 C17 H17B 108.0 . . ?
N3 C17 C18 117.1(2) . . ?
H17A C17 H17B 107.3 . . ?
C18 C17 H17A 108.0 . . ?
C18 C17 H17B 108.0 . . ?
N3A C17A H17C 108.2 . . ?
N3A C17A H17D 108.2 . . ?
N3A C17A C18A 116.5(2) . . ?
H17C C17A H17D 107.3 . . ?
C18A C17A H17C 108.2 . . ?
C18A C17A H17D 108.2 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17A C18A H18D 109.5 . . ?
C17A C18A H18E 109.5 . . ?
C17A C18A H18F 109.5 . . ?
H18D C18A H18E 109.5 . . ?
H18D C18A H18F 109.5 . . ?
H18E C18A H18F 109.5 . . ?
N3 C19 H19A 108.8 . . ?
N3 C19 H19B 108.8 . . ?
N3 C19 C20 113.7(2) . . ?
H19A C19 H19B 107.7 . . ?
C20 C19 H19A 108.8 . . ?
C20 C19 H19B 108.8 . . ?
N3A C19A H19C 109.2 . . ?
N3A C19A H19D 109.2 . . ?
N3A C19A C20A 111.9(3) . . ?
H19C C19A H19D 107.9 . . ?
C20A C19A H19C 109.2 . . ?
C20A C19A H19D 109.2 . . ?
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 . . ?
C19A C20A H20D 109.5 . . ?
C19A C20A H20E 109.5 . . ?
C19A C20A H20F 109.5 . . ?
H20D C20A H20E 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 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 C2 1.2050(19) . ?
O2 C3 1.2304(17) . ?
O3 C10 1.2456(17) . ?
N1 C1 1.4663(17) . ?
N1 C10 1.3926(18) . ?
N1 C14 1.368(2) . ?
N2 H2 0.88(2) . ?
N2 C3 1.326(2) . ?
N2 C15 1.4607(19) . ?
N3 C16 1.460(4) . ?
N3 C17 1.481(4) . ?
N3 C19 1.477(4) . ?
N3A C16A 1.465(4) . ?
N3A C17A 1.475(4) . ?
N3A C19A 1.465(4) . ?
C1 H1 1.0000 . ?
C1 C2 1.530(2) . ?
C1 C3 1.5412(18) . ?
C2 C4 1.486(2) . ?
C4 C5 1.416(15) . ?
C4 C5A 1.355(16) . ?
C4 C9 1.339(14) . ?
C4 C9A 1.469(12) . ?
C5 H5 0.9500 . ?
C5 C6 1.404(15) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.394(14) . ?
C6 H6 0.9500 . ?
C6 C7 1.376(8) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.373(9) . ?
C7 H7 0.9500 . ?
C7 C8 1.368(10) . ?
C7A H7A 0.9500 . ?
C7A C8A 1.377(10) . ?
C8 H8 0.9500 . ?
C8 C9 1.407(13) . ?
C8A H8A 0.9500 . ?
C8A C9A 1.352(14) . ?
C9 H9 0.9500 . ?
C9A H9A 0.9500 . ?
C10 C11 1.436(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.357(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.411(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.349(2) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 H15C 0.9900 . ?
C15 H15D 0.9900 . ?
C15 C16 1.429(3) . ?
C15 C16A 1.665(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16A H16C 0.9900 . ?
C16A H16D 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.524(4) . ?
C17A H17C 0.9900 . ?
C17A H17D 0.9900 . ?
C17A C18A 1.531(4) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C18A H18D 0.9800 . ?
C18A H18E 0.9800 . ?
C18A H18F 0.9800 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.503(5) . ?
C19A H19C 0.9900 . ?
C19A H19D 0.9900 . ?
C19A C20A 1.515(5) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C20A H20D 0.9800 . ?
C20A H20E 0.9800 . ?
C20A H20F 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 O3 0.88(2) 1.95(2) 2.8269(16) 171.7(18) 3_656 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 C2 C4 C5 179.6(4) . . . . ?
O1 C2 C4 C5A 161.0(4) . . . . ?
O1 C2 C4 C9 -6.1(8) . . . . ?
O1 C2 C4 C9A -9.6(6) . . . . ?
O3 C10 C11 C12 176.17(16) . . . . ?
N1 C1 C2 O1 -5.78(19) . . . . ?
N1 C1 C2 C4 172.53(11) . . . . ?
N1 C1 C3 O2 95.65(15) . . . . ?
N1 C1 C3 N2 -83.84(15) . . . . ?
N1 C10 C11 C12 -3.8(2) . . . . ?
N2 C15 C16 N3 57.6(2) . . . . ?
N2 C15 C16A N3A -51.9(3) . . . . ?
C1 N1 C10 O3 1.3(2) . . . . ?
C1 N1 C10 C11 -178.82(13) . . . . ?
C1 N1 C14 C13 -179.5(2) . . . . ?
C1 C2 C4 C5 1.4(4) . . . . ?
C1 C2 C4 C5A -17.3(4) . . . . ?
C1 C2 C4 C9 175.6(8) . . . . ?
C1 C2 C4 C9A 172.2(6) . . . . ?
C2 C1 C3 O2 -26.30(17) . . . . ?
C2 C1 C3 N2 154.21(12) . . . . ?
C2 C4 C5 C6 179.2(5) . . . . ?
C2 C4 C5A C6A -173.4(4) . . . . ?
C2 C4 C9 C8 -179.5(11) . . . . ?
C2 C4 C9A C8A 176.8(10) . . . . ?
C3 N2 C15 C16 79.85(19) . . . . ?
C3 N2 C15 C16A 139.25(17) . . . . ?
C3 C1 C2 O1 116.67(15) . . . . ?
C3 C1 C2 C4 -65.02(16) . . . . ?
C4 C5 C6 C7 -3.2(9) . . . . ?
C4 C5A C6A C7A 0.6(10) . . . . ?
C5 C4 C9 C8 -4.8(17) . . . . ?
C5 C6 C7 C8 2.4(11) . . . . ?
C5A C4 C9A C8A 6.2(16) . . . . ?
C5A C6A C7A C8A 0.6(15) . . . . ?
C6 C7 C8 C9 -2.7(16) . . . . ?
C6A C7A C8A C9A 2(2) . . . . ?
C7 C8 C9 C4 4(2) . . . . ?
C7A C8A C9A C4 -5(2) . . . . ?
C9 C4 C5 C6 4.1(10) . . . . ?
C9A C4 C5A C6A -4.2(10) . . . . ?
C10 N1 C1 C2 -87.93(15) . . . . ?
C10 N1 C1 C3 150.10(13) . . . . ?
C10 N1 C14 C13 -5.1(3) . . . . ?
C10 C11 C12 C13 -0.5(3) . . . . ?
C11 C12 C13 C14 2.2(4) . . . . ?
C12 C13 C14 N1 0.4(4) . . . . ?
C14 N1 C1 C2 86.84(19) . . . . ?
C14 N1 C1 C3 -35.1(2) . . . . ?
C14 N1 C10 O3 -173.41(17) . . . . ?
C14 N1 C10 C11 6.5(2) . . . . ?
C15 N2 C3 O2 4.1(2) . . . . ?
C15 N2 C3 C1 -176.46(12) . . . . ?
C16 N3 C17 C18 55.6(3) . . . . ?
C16 N3 C19 C20 169.5(3) . . . . ?
C16A N3A C17A C18A 74.0(3) . . . . ?
C16A N3A C19A C20A 176.9(3) . . . . ?
C17 N3 C16 C15 55.4(3) . . . . ?
C17 N3 C19 C20 -64.7(3) . . . . ?
C17A N3A C16A C15 178.7(2) . . . . ?
C17A N3A C19A C20A -57.4(3) . . . . ?
C19 N3 C16 C15 -179.1(2) . . . . ?
C19 N3 C17 C18 -68.4(3) . . . . ?
C19A N3A C16A C15 -54.3(3) . . . . ?
C19A N3A C17A C18A -53.4(4) . . . . ?
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
2.0000 -1.0000 -11.0000 0.3516 0.7511 0.5464
-6.0000 1.0000 10.0000 -0.3875 -0.8805 -0.0434
-8.0000 1.0000 1.0000 -0.0464 -0.5158 0.7860
8.0000 -1.0000 2.0000 -0.0803 0.3642 -0.9900
-3.0000 -5.0000 4.0000 -0.9888 0.1903 0.1353
-5.0000 4.0000 -2.0000 0.5957 -0.5456 0.6151
3.0000 -0.0000 -11.0000 0.5233 0.6907 0.4215
6.0000 1.0000 4.0000 0.1005 -0.0377 -0.9408
