#------------------------------------------------------------------------------
#$Date: 2022-01-26 14:29:16 +0200 (Wed, 26 Jan 2022) $
#$Revision: 272246 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/61/1566133.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_1566133
loop_
_publ_author_name
'Quy, Alex S.'
'Li, Xingjian'
'Male, Louise'
'Stankovic, Tatjana'
'Agathanggelou, Angelo'
'Fossey, John S.'
_publ_section_title
;
 Aniline-containing derivatives of parthenolide: Synthesis and
 anti-chronic lymphocytic leukaemia activity
;
_journal_issue                   48
_journal_name_full               Tetrahedron
_journal_page_first              131631
_journal_paper_doi               10.1016/j.tet.2020.131631
_journal_volume                  76
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H27 N O4, C3 H6 O'
_chemical_formula_sum            'C24 H33 N O5'
_chemical_formula_weight         415.51
_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     direct
_cell_angle_alpha                90
_cell_angle_beta                 107.1578(16)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.34175(18)
_cell_length_b                   8.21411(13)
_cell_length_c                   12.44906(19)
_cell_measurement_reflns_used    18852
_cell_measurement_temperature    99.98(12)
_cell_measurement_theta_max      73.8870
_cell_measurement_theta_min      3.6710
_cell_volume                     1108.17(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(12)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3537
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    7.00   34.00   1.0000    1.3950
omega____ theta____ kappa____ phi______ frames
    -       42.0000   87.0000   41.4590 27

#__ type_ start__ end____ width___ exp.time_
  2 omega -113.00  -16.00   1.0000    1.3950
omega____ theta____ kappa____ phi______ frames
    -      -42.4357  -57.0000 -150.0000 97

#__ type_ start__ end____ width___ exp.time_
  3 omega -121.00   -6.00   1.0000    1.3950
omega____ theta____ kappa____ phi______ frames
    -      -42.4357  -19.0000   90.0000 115

#__ type_ start__ end____ width___ exp.time_
  4 omega -113.00  -16.00   1.0000    1.3950
omega____ theta____ kappa____ phi______ frames
    -      -42.4357  -57.0000  -60.0000 97

#__ type_ start__ end____ width___ exp.time_
  5 omega -115.00  -20.00   1.0000    1.3950
omega____ theta____ kappa____ phi______ frames
    -      -42.4357  -38.0000    0.0000 95

#__ type_ start__ end____ width___ exp.time_
  6 omega   23.00   97.00   1.0000    1.3950
omega____ theta____ kappa____ phi______ frames
    -       42.4357 -125.0000    0.0000 74

#__ type_ start__ end____ width___ exp.time_
  7 omega   14.00  113.00   1.0000    1.3950
omega____ theta____ kappa____ phi______ frames
    -       42.4357   65.0000   61.9032 99

#__ type_ start__ end____ width___ exp.time_
  8 omega   23.00   97.00   1.0000    1.3950
omega____ theta____ kappa____ phi______ frames
    -       42.4357 -125.0000 -150.0000 74

#__ type_ start__ end____ width___ exp.time_
  9 omega    1.00   82.00   1.0000    1.3950
omega____ theta____ kappa____ phi______ frames
    -       42.4357  -99.0000   90.0000 81

#__ type_ start__ end____ width___ exp.time_
 10 omega   14.00   46.00   1.0000    1.3950
omega____ theta____ kappa____ phi______ frames
    -       46.0000   81.0000  140.9322 32

#__ type_ start__ end____ width___ exp.time_
 11 omega   17.00   45.00   1.0000    1.3950
omega____ theta____ kappa____ phi______ frames
    -       50.0000   82.0000  -77.6395 28

#__ type_ start__ end____ width___ exp.time_
 12 omega   17.00   45.00   1.0000    1.3950
omega____ theta____ kappa____ phi______ frames
    -       50.0000   82.0000 -151.7162 28

#__ type_ start__ end____ width___ exp.time_
 13 omega   27.00  131.00   1.0000    1.3950
omega____ theta____ kappa____ phi______ frames
    -       58.0000   75.0000  168.8449 104

#__ type_ start__ end____ width___ exp.time_
 14 omega   31.00  136.00   1.0000    1.3950
omega____ theta____ kappa____ phi______ frames
    -       62.0000   77.0000   62.9293 105

#__ type_ start__ end____ width___ exp.time_
 15 omega   31.00  135.00   1.0000    1.3950
omega____ theta____ kappa____ phi______ frames
    -       62.0000   76.0000    3.0156 104

#__ type_ start__ end____ width___ exp.time_
 16 omega   32.00  134.00   1.0000    1.3950
omega____ theta____ kappa____ phi______ frames
    -       62.0000   73.0000  -85.7784 102

#__ type_ start__ end____ width___ exp.time_
 17 omega   35.00  140.00   1.0000    1.3950
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000   90.8591 105

#__ type_ start__ end____ width___ exp.time_
 18 omega   35.00  139.00   1.0000    1.3950
omega____ theta____ kappa____ phi______ frames
    -       66.0000   74.0000  -37.8503 104

#__ type_ start__ end____ width___ exp.time_
 19 omega   35.00  139.00   1.0000    1.3950
omega____ theta____ kappa____ phi______ frames
    -       66.0000   76.0000  118.3799 104

#__ type_ start__ end____ width___ exp.time_
 20 omega   39.00  143.00   1.0000    1.3950
omega____ theta____ kappa____ phi______ frames
    -       70.0000   75.0000 -151.4715 104

#__ type_ start__ end____ width___ exp.time_
 21 omega   45.00  141.00   1.0000    1.3950
omega____ theta____ kappa____ phi______ frames
    -       70.0000   51.0000 -156.6275 96

#__ type_ start__ end____ width___ exp.time_
 22 omega   43.00  148.00   1.0000    1.3950
omega____ theta____ kappa____ phi______ frames
    -       74.0000   77.0000  123.7087 105

#__ type_ start__ end____ width___ exp.time_
 23 omega   46.00  144.00   1.0000    1.3950
omega____ theta____ kappa____ phi______ frames
    -       74.0000   63.0000    6.5051 98

#__ type_ start__ end____ width___ exp.time_
 24 omega   44.00  146.00   1.0000    1.3950
omega____ theta____ kappa____ phi______ frames
    -       74.0000   72.0000   19.3713 102

#__ type_ start__ end____ width___ exp.time_
 25 omega   43.00  147.00   1.0000    1.3950
omega____ theta____ kappa____ phi______ frames
    -       74.0000   76.0000  -83.0060 104

#__ type_ start__ end____ width___ exp.time_
 26 omega   55.00  152.00   1.0000    5.5750
omega____ theta____ kappa____ phi______ frames
    -       82.0000   60.0000   71.3805 97

#__ type_ start__ end____ width___ exp.time_
 27 omega   52.00  154.00   1.0000    5.5750
omega____ theta____ kappa____ phi______ frames
    -       82.0000   70.0000   93.3808 102

#__ type_ start__ end____ width___ exp.time_
 28 omega   59.00  156.00   1.0000    5.5750
omega____ theta____ kappa____ phi______ frames
    -       86.0000   60.0000  -99.9646 97

#__ type_ start__ end____ width___ exp.time_
 29 omega   58.00  156.00   1.0000    5.5750
omega____ theta____ kappa____ phi______ frames
    -       86.0000   61.0000  -12.4797 98

#__ type_ start__ end____ width___ exp.time_
 30 omega   59.00  163.00   1.0000    5.5750
omega____ theta____ kappa____ phi______ frames
    -       90.0000   76.0000  -55.4984 104

#__ type_ start__ end____ width___ exp.time_
 31 omega   68.00  170.00   1.0000    5.5750
omega____ theta____ kappa____ phi______ frames
    -       98.0000   72.0000  -81.3507 102

#__ type_ start__ end____ width___ exp.time_
 32 omega   94.00  178.00   1.0000    5.5750
omega____ theta____ kappa____ phi______ frames
    -      106.6257  125.0000 -150.0000 84

#__ type_ start__ end____ width___ exp.time_
 33 omega   75.00  178.00   1.0000    5.5750
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000  150.0000 103

#__ type_ start__ end____ width___ exp.time_
 34 omega   75.00  178.00   1.0000    5.5750
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000   60.0000 103

#__ type_ start__ end____ width___ exp.time_
 35 omega   75.00  178.00   1.0000    5.5750
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000 -180.0000 103

#__ type_ start__ end____ width___ exp.time_
 36 omega   25.00  109.00   1.0000    5.5750
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000  -30.0000 84

#__ type_ start__ end____ width___ exp.time_
 37 omega   75.00  178.00   1.0000    5.5750
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000  -60.0000 103

#__ type_ start__ end____ width___ exp.time_
 38 omega   25.00  109.00   1.0000    5.5750
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000  120.0000 84

#__ type_ start__ end____ width___ exp.time_
 39 omega   79.00  177.00   1.0000    5.5750
omega____ theta____ kappa____ phi______ frames
    -      106.6257   61.0000  150.0000 98

#__ type_ start__ end____ width___ exp.time_
 40 omega   35.00   99.00   1.0000    5.5750
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -45.0000  -30.0000 64

#__ type_ start__ end____ width___ exp.time_
 41 omega   75.00  178.00   1.0000    5.5750
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000    0.0000 103

#__ type_ start__ end____ width___ exp.time_
 42 omega   35.00  122.00   1.0000    5.5750
omega____ theta____ kappa____ phi______ frames
    -      106.6257 -125.0000  -60.0000 87

#__ type_ start__ end____ width___ exp.time_
 43 omega   75.00  178.00   1.0000    5.5750
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000  -30.0000 103

#__ type_ start__ end____ width___ exp.time_
 44 omega   79.00  177.00   1.0000    5.5750
omega____ theta____ kappa____ phi______ frames
    -      106.6257   61.0000  123.6998 98

#__ type_ start__ end____ width___ exp.time_
 45 omega   75.00  178.00   1.0000    5.5750
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000  120.0000 103

#__ type_ start__ end____ width___ exp.time_
 46 omega   75.00  178.00   1.0000    5.5750
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000   90.0000 103

#__ type_ start__ end____ width___ exp.time_
 47 omega   79.00  177.00   1.0000    5.5750
omega____ theta____ kappa____ phi______ frames
    -      106.6257   61.0000 -150.0000 98

#__ type_ start__ end____ width___ exp.time_
 48 omega   75.00  178.00   1.0000    5.5750
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000   30.0000 103

#__ type_ start__ end____ width___ exp.time_
 49 omega   25.00  109.00   1.0000    5.5750
omega____ theta____ kappa____ phi______ frames
    -      106.6257  -94.0000 -180.0000 84

#__ type_ start__ end____ width___ exp.time_
 50 omega   75.00  178.00   1.0000    5.5750
omega____ theta____ kappa____ phi______ frames
    -      106.6257   77.0000 -120.0000 103

#__ type_ start__ end____ width___ exp.time_
 51 omega    7.00   33.00   1.0000    1.3950
omega____ theta____ kappa____ phi______ frames
    -       42.0000   89.0000  -77.7349 26

#__ type_ start__ end____ width___ exp.time_
 52 omega  -50.00   30.00   1.0000    1.3950
omega____ theta____ kappa____ phi______ frames
    -      -42.4357   38.0000 -180.0000 80

#__ type_ start__ end____ width___ exp.time_
 53 omega -121.00   -6.00   1.0000    1.3950
omega____ theta____ kappa____ phi______ frames
    -      -42.4357  -19.0000  -60.0000 115

#__ type_ start__ end____ width___ exp.time_
 54 omega   18.00   47.00   1.0000    1.3950
omega____ theta____ kappa____ phi______ frames
    -       50.0000   79.0000   58.0839 29

#__ type_ start__ end____ width___ exp.time_
 55 omega   27.00  131.00   1.0000    1.3950
omega____ theta____ kappa____ phi______ frames
    -       58.0000   76.0000   46.7335 104

#__ type_ start__ end____ width___ exp.time_
 56 omega   27.00  131.00   1.0000    1.3950
omega____ theta____ kappa____ phi______ frames
    -       58.0000   75.0000 -150.4686 104

#__ type_ start__ end____ width___ exp.time_
 57 omega   33.00  133.00   1.0000    1.3950
omega____ theta____ kappa____ phi______ frames
    -       62.0000   66.0000  -89.9884 100

#__ type_ start__ end____ width___ exp.time_
 58 omega   39.00  143.00   1.0000    1.3950
omega____ theta____ kappa____ phi______ frames
    -       70.0000   75.0000  -60.9584 104

#__ type_ start__ end____ width___ exp.time_
 59 omega   40.00  142.00   1.0000    1.3950
omega____ theta____ kappa____ phi______ frames
    -       70.0000   71.0000   71.6763 102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1021187000
_diffrn_orient_matrix_UB_12      -0.0311481000
_diffrn_orient_matrix_UB_13      0.0561709000
_diffrn_orient_matrix_UB_21      -0.0975466000
_diffrn_orient_matrix_UB_22      0.0015585000
_diffrn_orient_matrix_UB_23      -0.1162691000
_diffrn_orient_matrix_UB_31      0.0164012000
_diffrn_orient_matrix_UB_32      -0.1848841000
_diffrn_orient_matrix_UB_33      -0.0103850000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            39001
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.439
_diffrn_reflns_theta_min         3.716
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.699
_exptl_absorpt_correction_T_max  0.809
_exptl_absorpt_correction_T_min  0.508
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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            grey
_exptl_crystal_colour_primary    grey
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_description       rod
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.2589
_exptl_crystal_size_mid          0.1037
_exptl_crystal_size_min          0.0591
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1819 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4374
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0323
_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)+(0.0490P)²+0.2580P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0837
_refine_ls_wR_factor_ref         0.0857
_reflns_Friedel_coverage         0.809
_reflns_Friedel_fraction_full    0.961
_reflns_Friedel_fraction_max     0.931
_reflns_number_gt                4185
_reflns_number_total             4374
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            3b.cif
_cod_data_source_block           3b
_cod_database_code               1566133
_chemical_oxdiff_formula         'C12 H27 N 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.
;
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C9(H9), C10(H10), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C7(H7A,H7B), C8(H8A,H8B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C17(H17), C18(H18), C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C102(H10A,H10B,H10C), C103(H10D,
 H10E,H10F)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
C1 C 0.60954(18) 0.6071(3) 1.01975(16) 0.0210(4) Uani 1 1 d . . . . .
H1 H 0.5999 0.7244 1.0286 0.025 Uiso 1 1 calc R . . . .
C2 C 0.70168(18) 0.5297(3) 1.11449(15) 0.0220(4) Uani 1 1 d . . . . .
C3 C 0.7702(2) 0.6399(3) 1.20957(17) 0.0254(4) Uani 1 1 d . . . . .
H3A H 0.7960 0.5784 1.2791 0.030 Uiso 1 1 calc R . . . .
H3B H 0.7161 0.7268 1.2188 0.030 Uiso 1 1 calc R . . . .
C4 C 0.8844(2) 0.7131(3) 1.18393(18) 0.0283(5) Uani 1 1 d . . . . .
H4A H 0.9203 0.7970 1.2386 0.034 Uiso 1 1 calc R . . . .
H4B H 0.9459 0.6289 1.1896 0.034 Uiso 1 1 calc R . . . .
C5 C 0.84826(19) 0.7851(3) 1.06738(18) 0.0260(4) Uani 1 1 d . . . . .
H5 H 0.8022 0.8805 1.0577 0.031 Uiso 1 1 calc R . . . .
C6 C 0.87424(18) 0.7289(3) 0.97644(18) 0.0238(4) Uani 1 1 d . . . . .
C7 C 0.81267(19) 0.8024(3) 0.86240(18) 0.0255(4) Uani 1 1 d . . . . .
H7A H 0.8751 0.8232 0.8251 0.031 Uiso 1 1 calc R . . . .
H7B H 0.7769 0.9062 0.8729 0.031 Uiso 1 1 calc R . . . .
C8 C 0.71082(18) 0.6950(3) 0.78521(17) 0.0251(4) Uani 1 1 d . . . . .
H8A H 0.6923 0.7359 0.7089 0.030 Uiso 1 1 calc R . . . .
H8B H 0.7426 0.5853 0.7858 0.030 Uiso 1 1 calc R . . . .
C9 C 0.59025(18) 0.6874(3) 0.81765(16) 0.0205(4) Uani 1 1 d . . . . .
H9 H 0.5800 0.7921 0.8516 0.025 Uiso 1 1 calc R . . . .
C10 C 0.57808(18) 0.5511(3) 0.89937(16) 0.0209(4) Uani 1 1 d . . . . .
H10 H 0.6286 0.4569 0.8929 0.025 Uiso 1 1 calc R . . . .
C11 C 0.7653(2) 0.3726(3) 1.10221(19) 0.0260(4) Uani 1 1 d . . . . .
H11A H 0.7105 0.3065 1.0454 0.039 Uiso 1 1 calc GR . . . .
H11B H 0.7877 0.3152 1.1725 0.039 Uiso 1 1 calc GR . . . .
H11C H 0.8382 0.3961 1.0809 0.039 Uiso 1 1 calc GR . . . .
C12 C 0.9617(2) 0.5925(3) 0.97457(19) 0.0296(5) Uani 1 1 d . . . . .
H12A H 0.9969 0.5516 1.0495 0.044 Uiso 1 1 calc GR . . . .
H12B H 1.0263 0.6320 0.9460 0.044 Uiso 1 1 calc GR . . . .
H12C H 0.9178 0.5066 0.9270 0.044 Uiso 1 1 calc GR . . . .
C13 C 0.47651(19) 0.6605(3) 0.71511(16) 0.0214(4) Uani 1 1 d . . . . .
H13 H 0.4996 0.5941 0.6591 0.026 Uiso 1 1 calc R . . . .
C14 C 0.3882(2) 0.5664(3) 0.76172(17) 0.0233(4) Uani 1 1 d . . . . .
C15 C 0.42209(19) 0.8241(3) 0.66176(17) 0.0226(4) Uani 1 1 d . . . . .
H15A H 0.3936 0.8837 0.7167 0.027 Uiso 1 1 calc R . . . .
H15B H 0.4883 0.8871 0.6474 0.027 Uiso 1 1 calc R . . . .
C16 C 0.33965(19) 0.7738(3) 0.45693(17) 0.0217(4) Uani 1 1 d . . . . .
C17 C 0.45580(19) 0.7607(3) 0.44031(16) 0.0235(4) Uani 1 1 d . . . . .
H17 H 0.5261 0.7784 0.5005 0.028 Uiso 1 1 calc R . . . .
C18 C 0.46837(18) 0.7216(3) 0.33503(17) 0.0224(4) Uani 1 1 d . . . . .
H18 H 0.5465 0.7143 0.3256 0.027 Uiso 1 1 calc R . . . .
C19 C 0.36486(19) 0.6936(3) 0.24473(16) 0.0215(4) Uani 1 1 d . . . . .
C20 C 0.24831(19) 0.7094(3) 0.25937(17) 0.0237(4) Uani 1 1 d . . . . .
H20 H 0.1784 0.6937 0.1986 0.028 Uiso 1 1 calc R . . . .
C21 C 0.23565(19) 0.7482(3) 0.36339(17) 0.0231(4) Uani 1 1 d . . . . .
H21 H 0.1571 0.7576 0.3717 0.028 Uiso 1 1 calc R . . . .
N1 N 0.32205(17) 0.8165(3) 0.55897(14) 0.0253(4) Uani 1 1 d . . . . .
O1 O 0.56921(13) 0.5069(2) 1.09894(11) 0.0242(3) Uani 1 1 d . . . . .
O2 O 0.44705(13) 0.50735(19) 0.86513(12) 0.0247(3) Uani 1 1 d . . . . .
O3 O 0.27997(14) 0.5420(2) 0.71928(13) 0.0314(4) Uani 1 1 d . . . . .
O4 O 0.37012(15) 0.6518(2) 0.13881(12) 0.0255(3) Uani 1 1 d . . . . .
C101 C 0.9621(2) 0.7695(4) 0.5756(2) 0.0415(6) Uani 1 1 d . . . . .
C102 C 0.8334(3) 0.8299(6) 0.5204(3) 0.0628(10) Uani 1 1 d . . . . .
H10A H 0.7804 0.7392 0.4908 0.094 Uiso 1 1 calc GR . . . .
H10B H 0.8341 0.9029 0.4603 0.094 Uiso 1 1 calc GR . . . .
H10C H 0.8036 0.8863 0.5747 0.094 Uiso 1 1 calc GR . . . .
C103 C 0.9762(3) 0.6190(4) 0.6442(2) 0.0431(6) Uani 1 1 d . . . . .
H10D H 0.9205 0.6224 0.6891 0.065 Uiso 1 1 calc GR . . . .
H10E H 1.0595 0.6114 0.6925 0.065 Uiso 1 1 calc GR . . . .
H10F H 0.9579 0.5259 0.5955 0.065 Uiso 1 1 calc GR . . . .
O101 O 1.05173(19) 0.8438(4) 0.5658(2) 0.0682(8) Uani 1 1 d . . . . .
H1A H 0.246(2) 0.802(4) 0.565(2) 0.025(6) Uiso 1 1 d . . . . .
H4 H 0.439(3) 0.620(5) 0.143(3) 0.051(10) Uiso 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
_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 0 -8 0.0295 0.9986 0.0023 -8.0008 -0.5515 0.8328 0.0990
-1 0 8 0.0295 -0.9986 -0.0023 8.0008 0.5515 -0.8328 -0.0990
-1 5 4 0.1197 -0.9995 5.0026 4.0067 0.1713 -0.3606 -0.9829
-1 5 -2 0.1309 -1.0012 5.0045 -1.9932 -0.1656 0.3372 -0.9210
1 -4 -5 0.1060 0.9992 -4.0016 -5.0055 -0.2586 0.4783 0.8082
0 -4 5 0.0916 0.0013 -4.0045 4.9953 0.4052 -0.5872 0.6885
-7 0 3 0.0518 -7.0052 0.0004 3.0065 0.8842 0.3338 -0.1462
7 0 -3 0.0478 7.0052 -0.0004 -3.0065 -0.8842 -0.3338 0.1462
2 -5 -1 0.1143 2.0012 -5.0037 -1.0077 -0.1051 -0.0859 0.9684
0 5 1 0.1291 0.0005 5.0034 1.0058 -0.0994 -0.1092 -0.9355
-4 -4 1 0.1136 -4.0034 -4.0025 0.9991 0.5896 0.2681 0.6640
5 0 4 0.0346 5.0055 -0.0022 3.9952 -0.2867 -0.9528 0.0410
-5 0 -4 0.0493 -5.0055 0.0022 -3.9952 0.2867 0.9528 -0.0410
-4 0 8 0.0329 -4.0012 -0.0017 8.0036 0.8582 -0.5403 -0.1484
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
C2 C1 H1 114.3 . .
C2 C1 C10 124.76(18) . .
C10 C1 H1 114.3 . .
O1 C1 H1 114.3 . .
O1 C1 C2 60.25(12) . .
O1 C1 C10 118.12(17) . .
C1 C2 C3 116.69(19) . .
C1 C2 C11 122.47(18) . .
C11 C2 C3 116.19(18) . .
O1 C2 C1 59.46(12) . .
O1 C2 C3 116.70(17) . .
O1 C2 C11 112.28(17) . .
C2 C3 H3A 109.7 . .
C2 C3 H3B 109.7 . .
C2 C3 C4 109.91(17) . .
H3A C3 H3B 108.2 . .
C4 C3 H3A 109.7 . .
C4 C3 H3B 109.7 . .
C3 C4 H4A 109.6 . .
C3 C4 H4B 109.6 . .
H4A C4 H4B 108.1 . .
C5 C4 C3 110.20(17) . .
C5 C4 H4A 109.6 . .
C5 C4 H4B 109.6 . .
C4 C5 H5 116.0 . .
C6 C5 C4 128.0(2) . .
C6 C5 H5 116.0 . .
C5 C6 C7 120.2(2) . .
C5 C6 C12 125.7(2) . .
C12 C6 C7 114.08(19) . .
C6 C7 H7A 108.7 . .
C6 C7 H7B 108.7 . .
C6 C7 C8 114.22(18) . .
H7A C7 H7B 107.6 . .
C8 C7 H7A 108.7 . .
C8 C7 H7B 108.7 . .
C7 C8 H8A 108.6 . .
C7 C8 H8B 108.6 . .
H8A C8 H8B 107.5 . .
C9 C8 C7 114.85(17) . .
C9 C8 H8A 108.6 . .
C9 C8 H8B 108.6 . .
C8 C9 H9 107.8 . .
C8 C9 C10 117.48(17) . .
C8 C9 C13 112.38(16) . .
C10 C9 H9 107.8 . .
C13 C9 H9 107.8 . .
C13 C9 C10 103.06(16) . .
C1 C10 C9 113.12(18) . .
C1 C10 H10 110.5 . .
C9 C10 H10 110.5 . .
O2 C10 C1 106.66(15) . .
O2 C10 C9 105.43(15) . .
O2 C10 H10 110.5 . .
C2 C11 H11A 109.5 . .
C2 C11 H11B 109.5 . .
C2 C11 H11C 109.5 . .
H11A C11 H11B 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C6 C12 H12A 109.5 . .
C6 C12 H12B 109.5 . .
C6 C12 H12C 109.5 . .
H12A C12 H12B 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C9 C13 H13 109.6 . .
C9 C13 C15 111.25(17) . .
C14 C13 C9 104.08(16) . .
C14 C13 H13 109.6 . .
C14 C13 C15 112.61(17) . .
C15 C13 H13 109.6 . .
O2 C14 C13 110.61(17) . .
O3 C14 C13 128.60(19) . .
O3 C14 O2 120.8(2) . .
C13 C15 H15A 108.0 . .
C13 C15 H15B 108.0 . .
H15A C15 H15B 107.3 . .
N1 C15 C13 117.02(18) . .
N1 C15 H15A 108.0 . .
N1 C15 H15B 108.0 . .
C17 C16 C21 117.57(18) . .
N1 C16 C17 123.49(18) . .
N1 C16 C21 118.90(18) . .
C16 C17 H17 119.4 . .
C16 C17 C18 121.23(18) . .
C18 C17 H17 119.4 . .
C17 C18 H18 119.9 . .
C19 C18 C17 120.22(18) . .
C19 C18 H18 119.9 . .
C18 C19 C20 119.24(18) . .
O4 C19 C18 123.48(18) . .
O4 C19 C20 117.27(18) . .
C19 C20 H20 119.7 . .
C21 C20 C19 120.62(18) . .
C21 C20 H20 119.7 . .
C16 C21 H21 119.5 . .
C20 C21 C16 121.09(19) . .
C20 C21 H21 119.5 . .
C15 N1 H1A 117.6(16) . .
C16 N1 C15 122.43(17) . .
C16 N1 H1A 116.2(16) . .
C1 O1 C2 60.29(12) . .
C14 O2 C10 111.25(15) . .
C19 O4 H4 109(2) . .
C103 C101 C102 117.7(3) . .
O101 C101 C102 120.9(3) . .
O101 C101 C103 121.5(3) . .
C101 C102 H10A 109.5 . .
C101 C102 H10B 109.5 . .
C101 C102 H10C 109.5 . .
H10A C102 H10B 109.5 . .
H10A C102 H10C 109.5 . .
H10B C102 H10C 109.5 . .
C101 C103 H10D 109.5 . .
C101 C103 H10E 109.5 . .
C101 C103 H10F 109.5 . .
H10D C103 H10E 109.5 . .
H10D C103 H10F 109.5 . .
H10E C103 H10F 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 H1 0.9800 .
C1 C2 1.470(3) .
C1 C10 1.506(3) .
C1 O1 1.457(2) .
C2 C3 1.511(3) .
C2 C11 1.508(3) .
C2 O1 1.469(2) .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C3 C4 1.544(3) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C4 C5 1.507(3) .
C5 H5 0.9300 .
C5 C6 1.334(3) .
C6 C7 1.511(3) .
C6 C12 1.501(3) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C7 C8 1.543(3) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C8 C9 1.537(3) .
C9 H9 0.9800 .
C9 C10 1.546(3) .
C9 C13 1.540(3) .
C10 H10 0.9800 .
C10 O2 1.465(2) .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
C13 H13 0.9800 .
C13 C14 1.510(3) .
C13 C15 1.545(3) .
C14 O2 1.353(3) .
C14 O3 1.201(3) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C15 N1 1.439(3) .
C16 C17 1.397(3) .
C16 C21 1.408(3) .
C16 N1 1.388(3) .
C17 H17 0.9300 .
C17 C18 1.397(3) .
C18 H18 0.9300 .
C18 C19 1.384(3) .
C19 C20 1.393(3) .
C19 O4 1.381(2) .
C20 H20 0.9300 .
C20 C21 1.382(3) .
C21 H21 0.9300 .
N1 H1A 0.90(3) .
O4 H4 0.82(4) .
C101 C102 1.502(4) .
C101 C103 1.484(4) .
C101 O101 1.222(3) .
C102 H10A 0.9600 .
C102 H10B 0.9600 .
C102 H10C 0.9600 .
C103 H10D 0.9600 .
C103 H10E 0.9600 .
C103 H10F 0.9600 .
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
N1 H1A O101 0.90(3) 2.23(3) 3.100(3) 163(3) 1_455
O4 H4 O1 0.82(4) 1.95(4) 2.724(2) 158(3) 1_554
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
C1 C2 C3 C4 -86.8(2) . . . .
C1 C10 O2 C14 135.68(17) . . . .
C2 C1 C10 C9 -125.3(2) . . . .
C2 C1 C10 O2 119.2(2) . . . .
C2 C3 C4 C5 50.0(3) . . . .
C3 C2 O1 C1 106.7(2) . . . .
C3 C4 C5 C6 -108.7(3) . . . .
C4 C5 C6 C7 170.0(2) . . . .
C4 C5 C6 C12 -9.4(4) . . . .
C5 C6 C7 C8 -105.3(2) . . . .
C6 C7 C8 C9 73.5(2) . . . .
C7 C8 C9 C10 -90.4(2) . . . .
C7 C8 C9 C13 150.25(18) . . . .
C8 C9 C10 C1 97.0(2) . . . .
C8 C9 C10 O2 -146.79(17) . . . .
C8 C9 C13 C14 149.32(18) . . . .
C8 C9 C13 C15 -89.2(2) . . . .
C9 C10 O2 C14 15.2(2) . . . .
C9 C13 C14 O2 -14.1(2) . . . .
C9 C13 C14 O3 165.6(2) . . . .
C9 C13 C15 N1 174.52(16) . . . .
C10 C1 C2 C3 148.0(2) . . . .
C10 C1 C2 C11 -6.9(3) . . . .
C10 C1 C2 O1 -105.3(2) . . . .
C10 C1 O1 C2 116.0(2) . . . .
C10 C9 C13 C14 21.9(2) . . . .
C10 C9 C13 C15 143.42(17) . . . .
C11 C2 C3 C4 69.6(2) . . . .
C11 C2 O1 C1 -115.59(19) . . . .
C12 C6 C7 C8 74.2(2) . . . .
C13 C9 C10 C1 -138.84(17) . . . .
C13 C9 C10 O2 -22.7(2) . . . .
C13 C14 O2 C10 -0.7(2) . . . .
C13 C15 N1 C16 -73.2(3) . . . .
C14 C13 C15 N1 -69.1(2) . . . .
C15 C13 C14 O2 -134.71(18) . . . .
C15 C13 C14 O3 45.0(3) . . . .
C16 C17 C18 C19 -0.5(3) . . . .
C17 C16 C21 C20 0.9(3) . . . .
C17 C16 N1 C15 -10.9(3) . . . .
C17 C18 C19 C20 1.8(3) . . . .
C17 C18 C19 O4 -178.9(2) . . . .
C18 C19 C20 C21 -1.7(3) . . . .
C19 C20 C21 C16 0.4(3) . . . .
C21 C16 C17 C18 -0.8(3) . . . .
C21 C16 N1 C15 171.7(2) . . . .
N1 C16 C17 C18 -178.3(2) . . . .
N1 C16 C21 C20 178.4(2) . . . .
O1 C1 C2 C3 -106.70(19) . . . .
O1 C1 C2 C11 98.4(2) . . . .
O1 C1 C10 C9 162.97(16) . . . .
O1 C1 C10 O2 47.5(2) . . . .
O1 C2 C3 C4 -154.28(18) . . . .
O3 C14 O2 C10 179.6(2) . . . .
O4 C19 C20 C21 178.9(2) . . . .
