#------------------------------------------------------------------------------
#$Date: 2022-02-03 22:43:46 +0200 (Thu, 03 Feb 2022) $
#$Revision: 272473 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/93/4519302.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_4519302
loop_
_publ_author_name
'Su, Yong-Liang'
'Liu, Geng-Xin'
'De Angelis, Luca'
'He, Ru'
'Al-Sayyed, Ammar'
'Schanze, Kirk S.'
'Hu, Wen-Hao'
'Qiu, Huang'
'Doyle, Michael P.'
_publ_section_title
;
 Radical Cascade Multicomponent Minisci Reactions with Diazo Compounds
;
_journal_issue                   2
_journal_name_full               'ACS Catalysis'
_journal_page_first              1357
_journal_page_last               1363
_journal_paper_doi               10.1021/acscatal.1c05611
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C28 H37 N O3'
_chemical_formula_sum            'C28 H37 N O3'
_chemical_formula_weight         435.58
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-14
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.819(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.2805(5)
_cell_length_b                   9.5063(2)
_cell_length_c                   18.9097(3)
_cell_measurement_reflns_used    13453
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.5320
_cell_measurement_theta_min      3.2340
_cell_volume                     4898.04(16)
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω     31.00 119.00   0.50    1.57    --   46.75  53.00 -20.00  176
  2  ω     91.00 178.00   0.50    6.27    --  106.69  53.00 -20.00  174
  3  ω     92.00 169.00   0.50    6.27    --  106.69  61.00  30.00  154
  4  ω     92.00 176.00   0.50    6.27    --  106.69  61.00  55.48  168
  5  ω     94.00 129.00   0.50    6.27    --  106.69  61.00  90.00   70
  6  ω     34.00  71.00   0.50    6.27    --  106.69 -61.00  30.00   74
  7  ω     39.00  65.00   0.50    6.27    --  106.69 -61.00 -30.00   52
  8  ω     56.00  93.00   0.50    6.27    --  106.69 -77.00 -60.00   74
  9  ω     39.00  70.00   0.50    6.27    --  106.69 -61.00 -90.00   62
 10  ω     34.00  60.00   0.50    6.27    --  106.69 -53.00-165.00   52
 11  ω     34.00 105.00   0.50    6.27    --  106.69 -94.00-120.00  142
 12  ω     76.00 108.00   0.50    6.27    --  106.69-125.00-150.00   64
 13  ω     35.00  74.00   0.50    6.27    --  106.69-125.00-150.00   78
 14  ω     34.00  71.00   0.50    6.27    --  106.69 -61.00-120.00   74
 15  ω     92.00 176.00   0.50    6.27    --  106.69  30.00 -90.00  168
 16  ω     33.00 120.00   0.50    1.57    --   46.75  43.00 104.81  174
 17  ω     38.00  65.00   0.50    6.27    --  106.69 -61.00  60.00   54
 18  ω     35.00 101.00   0.50    6.27    --  106.69 -77.00 120.00  132
 19  ω    -25.00  60.00   0.50    1.57    --   46.75 -53.00-165.00  170
 20  ω    -60.00  26.00   0.50    1.57    --  -46.75  53.00 -20.00  172
 21  ω    -51.00 -16.00   0.50    6.27    --  -88.50  45.00 120.00   70
 22  ω    -51.00 -16.00   0.50    6.27    --  -88.50  45.00  90.00   70
 23  ω    -51.00 -16.00   0.50    6.27    --  -88.50  45.00 150.00   70
 24  ω    -60.00 -15.00   0.50    6.27    --  -88.50  53.00 -20.00   90
 25  ω    -71.00 -15.00   0.50    6.27    --  -88.50  61.00-120.00  112
 26  ω    -51.00 -16.00   0.50    6.27    --  -88.50  45.00-180.00   70
 27  ω    -71.00 -15.00   0.50    6.27    --  -88.50  61.00 -60.00  112
 28  ω   -119.00 -31.00   0.50    1.57    --  -46.75 -53.00-165.00  176
 29  ω   -119.00 -88.00   0.50    1.57    --  -46.75-125.00 -30.00   62
 30  ω   -160.00 -73.00   0.50    6.27    --  -88.50 -53.00-165.00  174
 31  ω   -160.00-100.00   0.50    6.27    --  -88.50 -94.00 -60.00  120
 32  ω   -160.00 -73.00   0.50    6.27    --  -88.50 -53.00  74.71  174
 33  ω   -160.00 -73.00   0.50    6.27    --  -88.50 -55.00  58.36  174
 34  ω   -160.00 -91.00   0.50    6.27    --  -88.50 -61.00 150.00  138
 35  ω   -161.00 -74.00   0.50    6.27    --  -88.50 -45.00  60.00  174
 36  ω   -163.00 -73.00   0.50    6.27    --  -88.50 -30.00  90.00  180
 37  ω   -160.00 -78.00   0.50    6.27    --  -88.50 -56.00 118.89  164
 38  ω   -160.00 -72.00   0.50    6.27    --  -88.50 -51.00  37.38  176
 39  ω   -160.00 -72.00   0.50    6.27    --  -88.50 -54.00  93.30  176
 40  ω   -160.00 -73.00   0.50    6.27    --  -88.50 -53.00 138.71  174
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0529935000
_diffrn_orient_matrix_UB_12      -0.0060218000
_diffrn_orient_matrix_UB_13      -0.0319697000
_diffrn_orient_matrix_UB_21      0.0162807000
_diffrn_orient_matrix_UB_22      -0.1043169000
_diffrn_orient_matrix_UB_23      -0.0567102000
_diffrn_orient_matrix_UB_31      -0.0110703000
_diffrn_orient_matrix_UB_32      -0.1239304000
_diffrn_orient_matrix_UB_33      0.0491254000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0663
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            43511
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.876
_diffrn_reflns_theta_min         3.244
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.592
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.797
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_description       needle
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.167
_exptl_crystal_size_mid          0.052
_exptl_crystal_size_min          0.034
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         5004
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0663
_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)+(0.0300P)²+9.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1442
_refine_ls_wR_factor_ref         0.1482
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4337
_reflns_number_total             5004
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs1c05611_si_002.cif
_cod_data_source_block           hpd335a
_cod_database_code               4519302
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N'
_chemical_oxdiff_usercomment     7-25-7-1
_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 99.94
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C15(H15A,H15B), C20(H20A,H20B), C22(H22A,H22B), C16(H16A,
 H16B), C23(H23A,H23B), C24(H24A,H24B), C27(H27A,H27B), C25(H25A,H25B),
 C28(H28A,H28B), C26(H26A,H26B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3A), C6(H6), C4(H4), C9(H9), C5(H5), C12(H12), C10(H10), C11(H11)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_olex2_exptl_crystal_mounting_method 'nylon loop'
_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 2.125
_oxdiff_exptl_absorpt_empirical_full_min 0.583
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
O2 O 0.09997(6) 0.0232(2) 0.37709(8) 0.0534(5) Uani 1 1 d . . . . .
O3 O 0.62208(6) 1.0849(2) 0.40960(9) 0.0518(4) Uani 1 1 d . . . . .
H3 H 0.637300 1.044843 0.379146 0.078 Uiso 1 1 calc R U . . .
N1 N 0.17074(6) 0.49992(19) 0.28157(8) 0.0331(4) Uani 1 1 d . . . . .
O1 O 0.13844(7) 0.1265(2) 0.47022(8) 0.0605(5) Uani 1 1 d . . . . .
C1 C 0.20897(7) 0.4231(2) 0.26969(10) 0.0312(4) Uani 1 1 d . . . . .
C2 C 0.22892(7) 0.4100(2) 0.19980(10) 0.0327(4) Uani 1 1 d . . . . .
C7 C 0.20544(7) 0.4844(2) 0.14239(10) 0.0338(4) Uani 1 1 d . . . . .
C13 C 0.14765(7) 0.5760(2) 0.22604(10) 0.0346(4) Uani 1 1 d . . . . .
C14 C 0.23412(7) 0.3511(2) 0.33395(9) 0.0328(4) Uani 1 1 d . . . . .
H14 H 0.254084 0.273776 0.316737 0.039 Uiso 1 1 calc R U . . .
C8 C 0.16390(7) 0.5717(2) 0.15650(10) 0.0356(5) Uani 1 1 d . . . . .
C3 C 0.27026(7) 0.3277(2) 0.18645(10) 0.0356(5) Uani 1 1 d . . . . .
H3A H 0.285885 0.278501 0.223610 0.043 Uiso 1 1 calc R U . . .
C21 C 0.30904(7) 0.5207(2) 0.33270(10) 0.0362(5) Uani 1 1 d . . . . .
H21A H 0.294324 0.580527 0.295925 0.043 Uiso 1 1 calc R U . . .
H21B H 0.327155 0.446981 0.309950 0.043 Uiso 1 1 calc R U . . .
C15 C 0.19840(8) 0.2896(2) 0.38543(10) 0.0362(5) Uani 1 1 d . . . . .
H15A H 0.217159 0.245553 0.424324 0.043 Uiso 1 1 calc R U . . .
H15B H 0.179725 0.365922 0.404928 0.043 Uiso 1 1 calc R U . . .
C20 C 0.26877(7) 0.4548(2) 0.37438(10) 0.0351(5) Uani 1 1 d . . . . .
H20A H 0.249031 0.529963 0.392822 0.042 Uiso 1 1 calc R U . . .
H20B H 0.284088 0.405679 0.414646 0.042 Uiso 1 1 calc R U . . .
C6 C 0.22421(8) 0.4710(2) 0.07442(10) 0.0400(5) Uani 1 1 d . . . . .
H6 H 0.208720 0.517750 0.036322 0.048 Uiso 1 1 calc R U . . .
C22 C 0.34451(8) 0.6079(2) 0.38006(10) 0.0383(5) Uani 1 1 d . . . . .
H22A H 0.326098 0.680799 0.402888 0.046 Uiso 1 1 calc R U . . .
H22B H 0.358875 0.547493 0.416881 0.046 Uiso 1 1 calc R U . . .
C16 C 0.16280(8) 0.1822(2) 0.35304(10) 0.0378(5) Uani 1 1 d . . . . .
H16A H 0.140826 0.228704 0.318594 0.045 Uiso 1 1 calc R U . . .
H16B H 0.181066 0.111628 0.328249 0.045 Uiso 1 1 calc R U . . .
C17 C 0.13312(8) 0.1112(2) 0.40692(11) 0.0412(5) Uani 1 1 d . . . . .
C23 C 0.38539(8) 0.6759(3) 0.34111(10) 0.0394(5) Uani 1 1 d . . . . .
H23A H 0.371641 0.748832 0.310206 0.047 Uiso 1 1 calc R U . . .
H23B H 0.400355 0.605925 0.311723 0.047 Uiso 1 1 calc R U . . .
C4 C 0.28821(8) 0.3180(2) 0.12003(11) 0.0396(5) Uani 1 1 d . . . . .
H4 H 0.315782 0.263420 0.112572 0.048 Uiso 1 1 calc R U . . .
C9 C 0.13892(8) 0.6563(3) 0.10467(11) 0.0428(5) Uani 1 1 d . . . . .
H9 H 0.149113 0.655540 0.058465 0.051 Uiso 1 1 calc R U . . .
C5 C 0.26466(8) 0.3908(3) 0.06356(11) 0.0425(5) Uani 1 1 d . . . . .
H5 H 0.276654 0.384426 0.018477 0.051 Uiso 1 1 calc R U . . .
C12 C 0.10813(8) 0.6622(3) 0.24216(11) 0.0418(5) Uani 1 1 d . . . . .
H12 H 0.097748 0.665474 0.288244 0.050 Uiso 1 1 calc R U . . .
C10 C 0.10026(8) 0.7386(3) 0.12115(12) 0.0477(6) Uani 1 1 d . . . . .
H10 H 0.084272 0.792805 0.086159 0.057 Uiso 1 1 calc R U . . .
C11 C 0.08450(8) 0.7422(3) 0.19017(12) 0.0477(6) Uani 1 1 d . . . . .
H11 H 0.058058 0.798567 0.201100 0.057 Uiso 1 1 calc R U . . .
C24 C 0.42474(8) 0.7402(3) 0.39100(12) 0.0478(6) Uani 1 1 d . . . . .
H24A H 0.409047 0.804682 0.422596 0.057 Uiso 1 1 calc R U . . .
H24B H 0.439550 0.665637 0.419804 0.057 Uiso 1 1 calc R U . . .
C27 C 0.54559(8) 0.9549(3) 0.37688(12) 0.0474(6) Uani 1 1 d . . . . .
H27A H 0.531069 1.039701 0.356501 0.057 Uiso 1 1 calc R U . . .
H27B H 0.560391 0.902839 0.339300 0.057 Uiso 1 1 calc R U . . .
C25 C 0.46511(8) 0.8184(3) 0.35550(12) 0.0471(6) Uani 1 1 d . . . . .
H25A H 0.451164 0.899906 0.331098 0.056 Uiso 1 1 calc R U . . .
H25B H 0.478885 0.757628 0.320362 0.056 Uiso 1 1 calc R U . . .
C28 C 0.58509(9) 0.9946(3) 0.43317(12) 0.0547(7) Uani 1 1 d . . . . .
H28A H 0.569442 1.039778 0.472139 0.066 Uiso 1 1 calc R U . . .
H28B H 0.600454 0.909015 0.451322 0.066 Uiso 1 1 calc R U . . .
C26 C 0.50616(9) 0.8666(3) 0.40789(12) 0.0568(7) Uani 1 1 d . . . . .
H26A H 0.491630 0.920172 0.445175 0.068 Uiso 1 1 calc R U . . .
H26B H 0.521403 0.783989 0.429548 0.068 Uiso 1 1 calc R U . . .
C18 C 0.07209(10) -0.0594(3) 0.42512(14) 0.0616(7) Uani 1 1 d . . . . .
H18A H 0.062807 -0.001670 0.464584 0.074 Uiso 1 1 calc R U . . .
H18B H 0.091827 -0.137203 0.443653 0.074 Uiso 1 1 calc R U . . .
C19 C 0.02800(11) -0.1131(4) 0.38641(17) 0.0735(9) Uani 1 1 d . . . . .
H19A H 0.037438 -0.166289 0.346129 0.110 Uiso 1 1 calc R U . . .
H19B H 0.007669 -0.035598 0.370781 0.110 Uiso 1 1 calc R U . . .
H19C H 0.010055 -0.172516 0.417030 0.110 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 0 -12 0.0254
-4 0 12 0.0225
-6 -5 7 0.0622
17 -1 2 0.0131
2 5 -8 0.0471
-17 1 -2 0.0206
2 6 0 0.0640
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
C17 O2 C18 116.18(18) . . ?
C28 O3 H3 109.5 . . ?
C1 N1 C13 119.70(16) . . ?
N1 C1 C2 122.81(17) . . ?
N1 C1 C14 116.50(16) . . ?
C2 C1 C14 120.63(17) . . ?
C7 C2 C1 118.36(18) . . ?
C3 C2 C1 123.27(18) . . ?
C3 C2 C7 118.38(18) . . ?
C2 C7 C8 118.33(17) . . ?
C6 C7 C2 118.68(19) . . ?
C6 C7 C8 122.99(18) . . ?
N1 C13 C8 122.33(19) . . ?
N1 C13 C12 117.54(18) . . ?
C12 C13 C8 120.09(19) . . ?
C1 C14 H14 107.9 . . ?
C1 C14 C20 110.40(17) . . ?
C15 C14 C1 113.76(16) . . ?
C15 C14 H14 107.9 . . ?
C15 C14 C20 108.88(15) . . ?
C20 C14 H14 107.9 . . ?
C13 C8 C7 118.45(18) . . ?
C13 C8 C9 117.8(2) . . ?
C9 C8 C7 123.72(19) . . ?
C2 C3 H3A 119.1 . . ?
C4 C3 C2 121.82(19) . . ?
C4 C3 H3A 119.1 . . ?
H21A C21 H21B 107.9 . . ?
C20 C21 H21A 109.2 . . ?
C20 C21 H21B 109.2 . . ?
C20 C21 C22 111.87(16) . . ?
C22 C21 H21A 109.2 . . ?
C22 C21 H21B 109.2 . . ?
C14 C15 H15A 108.6 . . ?
C14 C15 H15B 108.6 . . ?
H15A C15 H15B 107.6 . . ?
C16 C15 C14 114.60(16) . . ?
C16 C15 H15A 108.6 . . ?
C16 C15 H15B 108.6 . . ?
C14 C20 H20A 108.1 . . ?
C14 C20 H20B 108.1 . . ?
C21 C20 C14 116.60(16) . . ?
C21 C20 H20A 108.1 . . ?
C21 C20 H20B 108.1 . . ?
H20A C20 H20B 107.3 . . ?
C7 C6 H6 119.4 . . ?
C5 C6 C7 121.28(19) . . ?
C5 C6 H6 119.4 . . ?
C21 C22 H22A 108.7 . . ?
C21 C22 H22B 108.7 . . ?
H22A C22 H22B 107.6 . . ?
C23 C22 C21 114.03(17) . . ?
C23 C22 H22A 108.7 . . ?
C23 C22 H22B 108.7 . . ?
C15 C16 H16A 109.0 . . ?
C15 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C17 C16 C15 112.73(16) . . ?
C17 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
O2 C17 C16 111.91(17) . . ?
O1 C17 O2 122.7(2) . . ?
O1 C17 C16 125.4(2) . . ?
C22 C23 H23A 109.1 . . ?
C22 C23 H23B 109.1 . . ?
C22 C23 C24 112.63(17) . . ?
H23A C23 H23B 107.8 . . ?
C24 C23 H23A 109.1 . . ?
C24 C23 H23B 109.1 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.5(2) . . ?
C5 C4 H4 120.2 . . ?
C8 C9 H9 119.3 . . ?
C10 C9 C8 121.3(2) . . ?
C10 C9 H9 119.3 . . ?
C6 C5 C4 120.33(19) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C13 C12 H12 119.8 . . ?
C11 C12 C13 120.4(2) . . ?
C11 C12 H12 119.8 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.4(2) . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 120.0(2) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C23 C24 H24A 108.4 . . ?
C23 C24 H24B 108.4 . . ?
H24A C24 H24B 107.5 . . ?
C25 C24 C23 115.40(18) . . ?
C25 C24 H24A 108.4 . . ?
C25 C24 H24B 108.4 . . ?
H27A C27 H27B 108.0 . . ?
C28 C27 H27A 109.4 . . ?
C28 C27 H27B 109.4 . . ?
C26 C27 H27A 109.4 . . ?
C26 C27 H27B 109.4 . . ?
C26 C27 C28 111.1(2) . . ?
C24 C25 H25A 109.1 . . ?
C24 C25 H25B 109.1 . . ?
C24 C25 C26 112.69(19) . . ?
H25A C25 H25B 107.8 . . ?
C26 C25 H25A 109.1 . . ?
C26 C25 H25B 109.1 . . ?
O3 C28 C27 114.92(19) . . ?
O3 C28 H28A 108.5 . . ?
O3 C28 H28B 108.5 . . ?
C27 C28 H28A 108.5 . . ?
C27 C28 H28B 108.5 . . ?
H28A C28 H28B 107.5 . . ?
C27 C26 C25 115.4(2) . . ?
C27 C26 H26A 108.4 . . ?
C27 C26 H26B 108.4 . . ?
C25 C26 H26A 108.4 . . ?
C25 C26 H26B 108.4 . . ?
H26A C26 H26B 107.5 . . ?
O2 C18 H18A 110.0 . . ?
O2 C18 H18B 110.0 . . ?
O2 C18 C19 108.6(2) . . ?
H18A C18 H18B 108.3 . . ?
C19 C18 H18A 110.0 . . ?
C19 C18 H18B 110.0 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
O2 C17 1.337(3) . ?
O2 C18 1.445(3) . ?
O3 H3 0.8200 . ?
O3 C28 1.414(3) . ?
N1 C1 1.302(3) . ?
N1 C13 1.399(2) . ?
O1 C17 1.207(3) . ?
C1 C2 1.459(3) . ?
C1 C14 1.527(3) . ?
C2 C7 1.422(3) . ?
C2 C3 1.405(3) . ?
C7 C8 1.440(3) . ?
C7 C6 1.413(3) . ?
C13 C8 1.409(3) . ?
C13 C12 1.400(3) . ?
C14 H14 0.9800 . ?
C14 C15 1.527(3) . ?
C14 C20 1.542(3) . ?
C8 C9 1.416(3) . ?
C3 H3A 0.9300 . ?
C3 C4 1.373(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C20 1.518(3) . ?
C21 C22 1.530(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.517(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C6 H6 0.9300 . ?
C6 C5 1.365(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.512(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.493(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.522(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.402(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.362(3) . ?
C5 H5 0.9300 . ?
C12 H12 0.9300 . ?
C12 C11 1.378(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.394(3) . ?
C11 H11 0.9300 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C25 1.513(3) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 C28 1.524(3) . ?
C27 C26 1.506(3) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C26 1.529(3) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.469(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
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
N1 C1 C2 C7 -0.1(3) . . . . ?
N1 C1 C2 C3 179.8(2) . . . . ?
N1 C1 C14 C15 41.2(3) . . . . ?
N1 C1 C14 C20 -81.6(2) . . . . ?
N1 C13 C8 C7 0.7(3) . . . . ?
N1 C13 C8 C9 -177.99(19) . . . . ?
N1 C13 C12 C11 178.6(2) . . . . ?
C1 N1 C13 C8 0.8(3) . . . . ?
C1 N1 C13 C12 -177.08(19) . . . . ?
C1 C2 C7 C8 1.5(3) . . . . ?
C1 C2 C7 C6 -179.29(19) . . . . ?
C1 C2 C3 C4 -179.8(2) . . . . ?
C1 C14 C15 C16 58.0(2) . . . . ?
C1 C14 C20 C21 -57.9(2) . . . . ?
C2 C1 C14 C15 -141.64(19) . . . . ?
C2 C1 C14 C20 95.6(2) . . . . ?
C2 C7 C8 C13 -1.8(3) . . . . ?
C2 C7 C8 C9 176.8(2) . . . . ?
C2 C7 C6 C5 -1.3(3) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C7 C2 C3 C4 0.0(3) . . . . ?
C7 C8 C9 C10 -179.0(2) . . . . ?
C7 C6 C5 C4 0.8(3) . . . . ?
C13 N1 C1 C2 -1.1(3) . . . . ?
C13 N1 C1 C14 176.04(17) . . . . ?
C13 C8 C9 C10 -0.4(3) . . . . ?
C13 C12 C11 C10 -0.6(4) . . . . ?
C14 C1 C2 C7 -177.08(18) . . . . ?
C14 C1 C2 C3 2.8(3) . . . . ?
C14 C15 C16 C17 172.48(19) . . . . ?
C8 C7 C6 C5 177.9(2) . . . . ?
C8 C13 C12 C11 0.7(3) . . . . ?
C8 C9 C10 C11 0.4(4) . . . . ?
C3 C2 C7 C8 -178.36(19) . . . . ?
C3 C2 C7 C6 0.8(3) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C21 C22 C23 C24 -170.1(2) . . . . ?
C15 C14 C20 C21 176.57(18) . . . . ?
C15 C16 C17 O2 176.29(19) . . . . ?
C15 C16 C17 O1 -5.6(3) . . . . ?
C20 C14 C15 C16 -178.43(18) . . . . ?
C20 C21 C22 C23 -179.99(19) . . . . ?
C6 C7 C8 C13 179.1(2) . . . . ?
C6 C7 C8 C9 -2.4(3) . . . . ?
C22 C21 C20 C14 -173.42(18) . . . . ?
C22 C23 C24 C25 -176.2(2) . . . . ?
C17 O2 C18 C19 161.8(3) . . . . ?
C23 C24 C25 C26 -173.9(2) . . . . ?
C9 C10 C11 C12 0.1(4) . . . . ?
C12 C13 C8 C7 178.5(2) . . . . ?
C12 C13 C8 C9 -0.2(3) . . . . ?
C24 C25 C26 C27 -175.4(2) . . . . ?
C28 C27 C26 C25 -178.8(2) . . . . ?
C26 C27 C28 O3 -176.3(2) . . . . ?
C18 O2 C17 O1 -3.1(4) . . . . ?
C18 O2 C17 C16 175.1(2) . . . . ?
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
3.8067 -0.3270 -12.0861 0.1866 0.7815 -0.5954
-4.0054 -0.2723 12.0692 -0.1719 -0.7212 0.6710
-6.1968 -4.5835 7.2263 0.1250 -0.0326 0.9916
17.1266 -0.7446 2.1613 -0.9722 0.2339 0.0089
2.0960 4.7625 -7.7449 0.1078 -0.0235 -0.9939
-17.1266 0.7446 -2.1613 0.9722 -0.2339 -0.0089
2.0967 6.1261 -0.0289 -0.1471 -0.6033 -0.7838
