#------------------------------------------------------------------------------
#$Date: 2023-09-05 21:58:27 +0200 (Tue 05 de Sep de 2023) $
#$Revision: 286149 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/69/7246953.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_7246953
loop_
_publ_author_name
'Kehoe, Roberta A.'
'Light, Mark E.'
'Jones, David J.'
'McGlacken, Gerard P.'
_publ_section_title
;
 A phosphine free, inorganic base free, one-pot tandem Mizoroki--Heck
 olefination/direct arylation/hydrogenation sequence, to give multicyclic
 alkylated heteroarenes
;
_journal_issue                   14
_journal_name_full               'Green Chemistry'
_journal_page_first              5654
_journal_page_last               5660
_journal_paper_doi               10.1039/D3GC01403G
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C23 H23 N O3'
_chemical_formula_sum            'C23 H23 N O3'
_chemical_formula_weight         361.42
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-08-15
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2022.06.10 svn.r3fa896fb for OlexSys, GUI svn.r6535)
;
_audit_update_record
;
2022-08-15 deposited with the CCDC.	2023-06-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.864(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0444(9)
_cell_length_b                   5.6218(3)
_cell_length_c                   27.7622(17)
_cell_measurement_reflns_used    2681
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.8540
_cell_measurement_theta_min      3.9550
_cell_volume                     1852.0(2)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.834
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -18.00  28.00   0.50  100.00    --   11.29 -77.00 -30.00   92
  2  ω      0.00  59.00   0.50  100.00    --   11.29  57.00 -30.00  118
  3  ω     22.00  62.00   0.50  100.00    --   11.29  57.00-180.00   80
  4  ω    -18.00   9.00   0.50  100.00    --   11.29 -77.00 -90.00   54
  5  ω     21.00  89.00   0.50  100.00    --   11.29  19.00 -90.00  136
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0580358000
_diffrn_orient_matrix_UB_12      -0.0051950000
_diffrn_orient_matrix_UB_13      -0.0103479000
_diffrn_orient_matrix_UB_21      -0.0138610000
_diffrn_orient_matrix_UB_22      -0.0112574000
_diffrn_orient_matrix_UB_23      0.0237219000
_diffrn_orient_matrix_UB_31      -0.0036953000
_diffrn_orient_matrix_UB_32      0.1255317000
_diffrn_orient_matrix_UB_33      0.0016749000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_av_unetI/netI     0.1001
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.834
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            12007
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.834
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.328
_diffrn_reflns_theta_min         3.919
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
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    1.296
_exptl_crystal_description       prism
_exptl_crystal_F_000             768
_exptl_crystal_recrystallization_method
'The material was recrystallised from --- by slow evaporation'
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         4623
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.1270
_refine_ls_R_factor_gt           0.0530
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0511P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1166
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2595
_reflns_number_total             4623
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3gc01403g2.cif
_cod_data_source_block           2022acc0019_r1_100k
_cod_depositor_comments
'Adding full bibliography for 7246950--7246958.cif.'
_cod_database_code               7246953
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C20 H20 N1 S1 O4'
_chemical_oxdiff_usercomment     EA-8-552
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.992
_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 Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C12(H12), C13(H13), C16(H16), C18(H18), C19(H19), C21(H21)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C23(H23A,H23B,H23C)
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder with silicon oil'
_olex2_submission_original_sample_id EA-8-552
_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 1.904
_oxdiff_exptl_absorpt_empirical_full_min 0.546
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 0.86669(10) 1.2678(2) 0.46303(4) 0.0229(3) Uani 1 1 d . . . . .
O2 O 0.69728(12) 1.4484(2) 0.44885(5) 0.0417(4) Uani 1 1 d . . . . .
O3 O 0.76307(10) 0.43450(19) 0.63751(4) 0.0209(3) Uani 1 1 d . . . . .
N1 N 0.48213(12) 0.7120(2) 0.68531(5) 0.0233(4) Uani 1 1 d . . . . .
C1 C 0.83932(17) 1.2893(3) 0.37387(6) 0.0296(5) Uani 1 1 d . . . . .
H1A H 0.836197 1.115211 0.374747 0.044 Uiso 1 1 calc R U . . .
H1B H 0.874489 1.339996 0.346239 0.044 Uiso 1 1 calc R U . . .
H1C H 0.762738 1.353909 0.370080 0.044 Uiso 1 1 calc R U . . .
C2 C 0.90836(16) 1.3806(3) 0.42123(6) 0.0234(4) Uani 1 1 d . . . . .
C3 C 1.02889(17) 1.2939(3) 0.42751(7) 0.0310(5) Uani 1 1 d . . . . .
H3A H 1.071478 1.356685 0.458118 0.047 Uiso 1 1 calc R U . . .
H3B H 1.063276 1.349143 0.399991 0.047 Uiso 1 1 calc R U . . .
H3C H 1.029984 1.119622 0.428504 0.047 Uiso 1 1 calc R U . . .
C4 C 0.90579(19) 1.6507(3) 0.42515(7) 0.0317(5) Uani 1 1 d . . . . .
H4A H 0.827401 1.705566 0.419656 0.048 Uiso 1 1 calc R U . . .
H4B H 0.945185 1.720921 0.400505 0.048 Uiso 1 1 calc R U . . .
H4C H 0.943133 1.699484 0.457827 0.048 Uiso 1 1 calc R U . . .
C5 C 0.76141(16) 1.3076(3) 0.47114(7) 0.0255(4) Uani 1 1 d . . . . .
C6 C 0.73485(16) 1.1512(3) 0.51172(7) 0.0252(4) Uani 1 1 d . . . . .
H6A H 0.795783 1.166492 0.540411 0.030 Uiso 1 1 calc R U . . .
H6B H 0.732442 0.983268 0.500862 0.030 Uiso 1 1 calc R U . . .
C7 C 0.62341(15) 1.2148(3) 0.52674(6) 0.0219(4) Uani 1 1 d . . . . .
H7A H 0.626585 1.383484 0.537132 0.026 Uiso 1 1 calc R U . . .
H7B H 0.563407 1.200960 0.497660 0.026 Uiso 1 1 calc R U . . .
C8 C 0.59005(15) 1.0658(3) 0.56741(6) 0.0200(4) Uani 1 1 d . . . . .
C9 C 0.64843(15) 0.8685(3) 0.58695(6) 0.0196(4) Uani 1 1 d . . . . .
H9 H 0.712406 0.816116 0.574075 0.024 Uiso 1 1 calc R U . . .
C10 C 0.61412(14) 0.7422(3) 0.62616(6) 0.0185(4) Uani 1 1 d . . . . .
C11 C 0.51829(15) 0.8178(3) 0.64573(6) 0.0202(4) Uani 1 1 d . . . . .
C12 C 0.45822(15) 1.0172(3) 0.62401(7) 0.0231(4) Uani 1 1 d . . . . .
H12 H 0.392491 1.068787 0.635630 0.028 Uiso 1 1 calc R U . . .
C13 C 0.49333(15) 1.1367(3) 0.58654(6) 0.0221(4) Uani 1 1 d . . . . .
H13 H 0.451744 1.271366 0.572879 0.027 Uiso 1 1 calc R U . . .
C14 C 0.66945(14) 0.5444(3) 0.65016(6) 0.0186(4) Uani 1 1 d . . . . .
C15 C 0.63570(15) 0.4382(3) 0.68993(6) 0.0188(4) Uani 1 1 d . . . . .
C16 C 0.54017(15) 0.5300(3) 0.70640(6) 0.0229(4) Uani 1 1 d . . . . .
H16 H 0.516478 0.457729 0.733870 0.027 Uiso 1 1 calc R U . . .
C17 C 0.78831(15) 0.2495(3) 0.67110(6) 0.0192(4) Uani 1 1 d . . . . .
C18 C 0.87431(15) 0.0884(3) 0.67208(7) 0.0236(4) Uani 1 1 d . . . . .
H18 H 0.924468 0.095032 0.649173 0.028 Uiso 1 1 calc R U . . .
C19 C 0.88433(16) -0.0849(3) 0.70823(6) 0.0235(4) Uani 1 1 d . . . . .
H19 H 0.942579 -0.199999 0.709755 0.028 Uiso 1 1 calc R U . . .
C20 C 0.81142(15) -0.0962(3) 0.74264(6) 0.0228(4) Uani 1 1 d . . . . .
C21 C 0.72584(15) 0.0699(3) 0.74059(6) 0.0210(4) Uani 1 1 d . . . . .
H21 H 0.676287 0.065765 0.763771 0.025 Uiso 1 1 calc R U . . .
C22 C 0.71314(14) 0.2438(3) 0.70402(6) 0.0189(4) Uani 1 1 d . . . . .
C23 C 0.82619(17) -0.2876(3) 0.78153(7) 0.0280(4) Uani 1 1 d . . . . .
H23A H 0.881816 -0.235312 0.809511 0.042 Uiso 1 1 calc R U . . .
H23B H 0.852381 -0.434372 0.768084 0.042 Uiso 1 1 calc R U . . .
H23C H 0.753925 -0.316961 0.792177 0.042 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 0.0033 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
-1 5 2 0.0076
1 -5 -2 0.0076
1 0 5 0.0456
-1 0 -5 0.0456
-3 0 5 0.0060
3 0 -5 0.0060
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
C5 O1 C2 121.00(14) . . ?
C14 O3 C17 104.90(13) . . ?
C16 N1 C11 118.10(15) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
O1 C2 C1 108.93(14) . . ?
O1 C2 C3 102.63(14) . . ?
O1 C2 C4 110.89(14) . . ?
C1 C2 C4 112.56(16) . . ?
C3 C2 C1 111.29(16) . . ?
C3 C2 C4 110.11(17) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O1 C5 C6 110.81(15) . . ?
O2 C5 O1 124.44(17) . . ?
O2 C5 C6 124.75(17) . . ?
C5 C6 H6A 109.1 . . ?
C5 C6 H6B 109.1 . . ?
C5 C6 C7 112.32(15) . . ?
H6A C6 H6B 107.9 . . ?
C7 C6 H6A 109.1 . . ?
C7 C6 H6B 109.1 . . ?
C6 C7 H7A 108.3 . . ?
C6 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
C8 C7 C6 115.80(15) . . ?
C8 C7 H7A 108.3 . . ?
C8 C7 H7B 108.3 . . ?
C9 C8 C7 123.89(16) . . ?
C9 C8 C13 118.49(16) . . ?
C13 C8 C7 117.61(15) . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.67(16) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C11 120.38(15) . . ?
C14 C10 C9 125.68(16) . . ?
C14 C10 C11 113.91(15) . . ?
N1 C11 C10 124.16(15) . . ?
N1 C11 C12 118.18(15) . . ?
C12 C11 C10 117.63(15) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.89(16) . . ?
C13 C12 H12 119.6 . . ?
C8 C13 H13 119.0 . . ?
C12 C13 C8 121.91(16) . . ?
C12 C13 H13 119.0 . . ?
O3 C14 C10 125.07(15) . . ?
C15 C14 O3 112.05(15) . . ?
C15 C14 C10 122.88(16) . . ?
C14 C15 C16 118.15(16) . . ?
C14 C15 C22 106.23(15) . . ?
C16 C15 C22 135.61(16) . . ?
N1 C16 C15 122.77(16) . . ?
N1 C16 H16 118.6 . . ?
C15 C16 H16 118.6 . . ?
C18 C17 O3 125.62(16) . . ?
C18 C17 C22 123.01(16) . . ?
C22 C17 O3 111.36(14) . . ?
C17 C18 H18 121.7 . . ?
C17 C18 C19 116.68(17) . . ?
C19 C18 H18 121.7 . . ?
C18 C19 H19 118.8 . . ?
C18 C19 C20 122.39(17) . . ?
C20 C19 H19 118.8 . . ?
C19 C20 C23 120.42(16) . . ?
C21 C20 C19 119.29(16) . . ?
C21 C20 C23 120.30(17) . . ?
C20 C21 H21 120.4 . . ?
C20 C21 C22 119.28(17) . . ?
C22 C21 H21 120.4 . . ?
C17 C22 C15 105.46(14) . . ?
C17 C22 C21 119.34(16) . . ?
C21 C22 C15 135.20(16) . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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 1.483(2) . ?
O1 C5 1.344(2) . ?
O2 C5 1.201(2) . ?
O3 C14 1.383(2) . ?
O3 C17 1.3951(19) . ?
N1 C11 1.384(2) . ?
N1 C16 1.319(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.519(3) . ?
C2 C3 1.513(3) . ?
C2 C4 1.523(2) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.506(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.515(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.515(2) . ?
C8 C9 1.374(2) . ?
C8 C13 1.418(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.419(2) . ?
C10 C11 1.422(2) . ?
C10 C14 1.404(2) . ?
C11 C12 1.412(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.365(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.377(2) . ?
C15 C16 1.407(2) . ?
C15 C22 1.446(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.373(2) . ?
C17 C22 1.393(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.389(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.405(3) . ?
C20 C21 1.385(3) . ?
C20 C23 1.513(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.399(2) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
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 C5 C6 C7 171.99(15) . . . . ?
O2 C5 C6 C7 -8.3(3) . . . . ?
O3 C14 C15 C16 -179.10(15) . . . . ?
O3 C14 C15 C22 -0.23(19) . . . . ?
O3 C17 C18 C19 -179.12(15) . . . . ?
O3 C17 C22 C15 0.09(18) . . . . ?
O3 C17 C22 C21 -179.76(14) . . . . ?
N1 C11 C12 C13 176.51(16) . . . . ?
C2 O1 C5 O2 -6.6(3) . . . . ?
C2 O1 C5 C6 173.16(14) . . . . ?
C5 O1 C2 C1 -63.80(19) . . . . ?
C5 O1 C2 C3 178.15(15) . . . . ?
C5 O1 C2 C4 60.6(2) . . . . ?
C5 C6 C7 C8 179.95(14) . . . . ?
C6 C7 C8 C9 -6.7(2) . . . . ?
C6 C7 C8 C13 172.72(16) . . . . ?
C7 C8 C9 C10 177.90(15) . . . . ?
C7 C8 C13 C12 -178.39(16) . . . . ?
C8 C9 C10 C11 0.2(2) . . . . ?
C8 C9 C10 C14 -177.47(16) . . . . ?
C9 C8 C13 C12 1.0(2) . . . . ?
C9 C10 C11 N1 -176.88(16) . . . . ?
C9 C10 C11 C12 1.5(2) . . . . ?
C9 C10 C14 O3 -3.5(3) . . . . ?
C9 C10 C14 C15 176.02(16) . . . . ?
C10 C11 C12 C13 -1.9(2) . . . . ?
C10 C14 C15 C16 1.3(2) . . . . ?
C10 C14 C15 C22 -179.84(15) . . . . ?
C11 N1 C16 C15 -0.8(2) . . . . ?
C11 C10 C14 O3 178.64(15) . . . . ?
C11 C10 C14 C15 -1.8(2) . . . . ?
C11 C12 C13 C8 0.7(3) . . . . ?
C13 C8 C9 C10 -1.5(2) . . . . ?
C14 O3 C17 C18 178.71(17) . . . . ?
C14 O3 C17 C22 -0.23(17) . . . . ?
C14 C10 C11 N1 1.1(2) . . . . ?
C14 C10 C11 C12 179.43(15) . . . . ?
C14 C15 C16 N1 0.1(3) . . . . ?
C14 C15 C22 C17 0.08(18) . . . . ?
C14 C15 C22 C21 179.90(18) . . . . ?
C16 N1 C11 C10 0.2(2) . . . . ?
C16 N1 C11 C12 -178.16(15) . . . . ?
C16 C15 C22 C17 178.65(19) . . . . ?
C16 C15 C22 C21 -1.5(3) . . . . ?
C17 O3 C14 C10 179.88(15) . . . . ?
C17 O3 C14 C15 0.28(17) . . . . ?
C17 C18 C19 C20 -0.5(3) . . . . ?
C18 C17 C22 C15 -178.88(16) . . . . ?
C18 C17 C22 C21 1.3(3) . . . . ?
C18 C19 C20 C21 0.4(3) . . . . ?
C18 C19 C20 C23 -179.64(16) . . . . ?
C19 C20 C21 C22 0.6(3) . . . . ?
C20 C21 C22 C15 178.80(18) . . . . ?
C20 C21 C22 C17 -1.4(2) . . . . ?
C22 C15 C16 N1 -178.31(18) . . . . ?
C22 C17 C18 C19 -0.3(3) . . . . ?
C23 C20 C21 C22 -179.38(15) . . . . ?
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
-0.9886 4.9985 2.0220 0.0105 0.0054 0.6345
0.9886 -4.9985 -2.0220 -0.0105 -0.0054 -0.6345
0.9988 0.0001 4.9989 -0.1097 0.1047 0.0047
-0.9988 -0.0001 -4.9989 0.1097 -0.1047 -0.0047
-2.9978 -0.0007 4.9930 0.1223 0.1600 0.0194
2.9978 0.0007 -4.9930 -0.1223 -0.1600 -0.0194
