#------------------------------------------------------------------------------
#$Date: 2023-09-05 22:58:27 +0300 (Tue, 05 Sep 2023) $
#$Revision: 286149 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/69/7246954.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_7246954
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         'C19 H15 N O'
_chemical_formula_sum            'C19 H15 N O'
_chemical_formula_weight         273.32
_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             2022-09-02
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2022.06.10 svn.r3fa896fb for OlexSys, GUI svn.r6535)
;
_audit_update_record
;
2022-09-02 deposited with the CCDC.	2023-06-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.2680(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1980(2)
_cell_length_b                   5.61880(10)
_cell_length_c                   18.6771(3)
_cell_measurement_reflns_used    10038
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.8060
_cell_measurement_theta_min      3.3620
_cell_volume                     1373.91(4)
_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 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00   5.00   0.50    0.24    --   46.61 -29.00 155.00   50
  2  ω     47.00 103.00   0.50    0.96    --  101.75 -77.00  90.00  112
  3  ω     34.00  70.00   0.50    0.96    --  101.75 -61.00   0.00   72
  4  ω     31.00  64.00   0.50    0.96    --  101.75 -61.00 -90.00   66
  5  ω     29.00  72.00   0.50    0.96    --  101.75 -61.00-150.00   86
  6  ω     89.00 167.00   0.50    0.96    --  101.75  29.00 -43.00  156
  7  ω    125.00 152.00   0.50    0.96    --  101.75  61.00   0.00   54
  8  ω     81.00 107.00   0.50    0.96    --  101.75  77.00  30.00   52
  9  ω     86.00 115.00   0.50    0.96    --  101.75  61.00   0.00   58
 10  ω     90.00 121.00   0.50    0.96    --  101.75  45.00  30.00   62
 11  ω     79.00 104.00   0.50    0.96    --  101.75  77.00  90.00   50
 12  ω     31.00  78.00   0.50    0.24    --   46.61  77.00  30.00   94
 13  ω     24.00  75.00   0.50    0.24    --   46.61  77.00  60.00  102
 14  ω     39.00  80.00   0.50    0.24    --   46.61  57.00   0.00   82
 15  ω     39.00  66.00   0.50    0.24    --   46.61  37.00   0.00   54
 16  ω     56.00 118.00   0.50    0.24    --   46.61  29.00 -43.00  124
 17  ω     37.00 105.00   0.50    0.96    --  101.75-100.00 -89.40  136
 18  ω    -39.00  26.00   0.50    0.24    --  -46.61  37.00  90.00  130
 19  ω     -3.00  23.00   0.50    0.24    --  -46.61  19.00  90.00   52
 20  ω    -31.00  28.00   0.50    0.24    --  -46.61  29.00 -43.00  118
 21  ω   -101.00 -39.00   0.50    0.96    -- -103.00  77.00 -30.00  124
 22  ω    -63.00 -31.00   0.50    0.96    -- -103.00  61.00-120.00   64
 23  ω    -63.00 -37.00   0.50    0.96    -- -103.00  61.00  60.00   52
 24  ω    -58.00 -33.00   0.50    0.96    -- -103.00  61.00  90.00   50
 25  ω    -62.00 -31.00   0.50    0.96    -- -103.00  61.00 150.00   62
 26  ω   -114.00 -51.00   0.50    0.24    --  -46.61 -29.00 155.00  126
 27  ω   -105.00 -80.00   0.50    0.96    -- -103.00 -78.00  46.55   50
 28  ω   -105.00 -80.00   0.50    0.96    -- -103.00 -78.00  21.30   50
 29  ω   -106.00 -80.00   0.50    0.96    -- -103.00 -77.00  30.00   52
 30  ω   -169.00-126.00   0.50    0.96    -- -103.00 -78.00  46.55   86
 31  ω   -172.00-146.00   0.50    0.96    -- -103.00 -78.00  21.30   52
 32  ω   -114.00 -80.00   0.50    0.96    -- -103.00 -77.00  90.00   68
 33  ω   -105.00 -80.00   0.50    0.96    -- -103.00 -77.00 120.00   50
 34  ω   -161.00-135.00   0.50    0.96    -- -103.00 -77.00 120.00   52
 35  ω   -174.00-135.00   0.50    0.96    -- -103.00 -76.00  36.03   78
 36  ω   -106.00 -80.00   0.50    0.96    -- -103.00 -77.00  60.00   52
 37  ω   -106.00 -80.00   0.50    0.96    -- -103.00 -76.00 113.49   52
 38  ω   -111.00 -85.00   0.50    0.96    -- -103.00 -65.00  92.30   52
 39  ω   -113.00 -88.00   0.50    0.96    -- -103.00 -58.00 120.36   50
 40  ω   -113.00 -87.00   0.50    0.96    -- -103.00 -61.00  60.00   52
 41  ω   -112.00 -86.00   0.50    0.96    -- -103.00 -61.00  55.16   52
 42  ω   -107.00 -81.00   0.50    0.96    -- -103.00 -76.00  36.03   52
 43  ω   -117.00 -91.00   0.50    0.96    -- -103.00 -54.00  -1.93   52
 44  ω   -113.00 -87.00   0.50    0.96    -- -103.00 -61.00  30.00   52
 45  ω   -115.00 -89.00   0.50    0.96    -- -103.00 -53.00  36.45   52
 46  ω   -134.00 -90.00   0.50    0.96    -- -103.00 -46.00  34.43   88
 47  ω   -165.00 -88.00   0.50    0.96    -- -103.00 -58.00  61.33  154
 48  ω   -116.00 -90.00   0.50    0.96    -- -103.00 -48.00  90.37   52
 49  ω   -115.00 -89.00   0.50    0.96    -- -103.00 -51.00 102.40   52
 50  ω   -166.00 -92.00   0.50    0.96    -- -103.00 -46.00  76.29  148
 51  ω   -156.00 -91.00   0.50    0.96    -- -103.00 -45.00  90.00  130
 52  ω   -118.00 -92.00   0.50    0.96    -- -103.00 -45.00 120.00   52
 53  ω   -156.00-131.00   0.50    0.96    -- -103.00 -29.00 155.00   50
 54  ω   -174.00-145.00   0.50    0.96    -- -103.00 -45.00 120.00   58
 55  ω   -106.00 -80.00   0.50    0.96    -- -103.00 -81.00  91.09   52
 56  ω   -104.00 -78.00   0.50    0.96    -- -103.00 -84.00 108.14   52
 57  ω   -137.00-107.00   0.50    0.96    -- -103.00-125.00 -90.00   60
 58  ω   -171.00-142.00   0.50    0.96    -- -103.00-125.00 -90.00   58
;
_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      -0.0576883000
_diffrn_orient_matrix_UB_12      -0.0570386000
_diffrn_orient_matrix_UB_13      -0.0749742000
_diffrn_orient_matrix_UB_21      0.1005489000
_diffrn_orient_matrix_UB_22      -0.0843273000
_diffrn_orient_matrix_UB_23      -0.0255981000
_diffrn_orient_matrix_UB_31      -0.0203465000
_diffrn_orient_matrix_UB_32      -0.2545322000
_diffrn_orient_matrix_UB_33      0.0252459000
_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  0.1188
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            19810
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.889
_diffrn_reflns_theta_min         3.376
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.639
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42170
_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    1.321
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_recrystallization_method
'The material was recrystallised from --- by slow evaporation'
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2774
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0564
_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)+(0.1035P)²+0.4243P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1520
_refine_ls_wR_factor_ref         0.1564
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2494
_reflns_number_total             2774
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3gc01403g2.cif
_cod_data_source_block           2022acc0025_a1_100k
_cod_depositor_comments
'Adding full bibliography for 7246950--7246958.cif.'
_cod_database_code               7246954
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C12H12 N1O1'
_chemical_oxdiff_usercomment     RAK-443
_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   0.975
_shelx_estimated_absorpt_t_min   0.789
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C8(H8), C9(H9), C10(H10), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19)
;
_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 RAK-443
_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 4.909
_oxdiff_exptl_absorpt_empirical_full_min 0.177
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
C1 C 0.53007(10) 0.5012(3) 0.63373(8) 0.0195(3) Uani 1 1 d . . . . .
C2 C 0.46176(10) 0.4578(3) 0.68370(9) 0.0221(3) Uani 1 1 d . . . . .
H2 H 0.472263 0.323356 0.714607 0.027 Uiso 1 1 calc R U . . .
C3 C 0.36747(11) 0.7883(3) 0.64434(9) 0.0237(4) Uani 1 1 d . . . . .
H3 H 0.310448 0.888012 0.648720 0.028 Uiso 1 1 calc R U . . .
C4 C 0.42953(11) 0.8483(3) 0.59192(9) 0.0238(4) Uani 1 1 d . . . . .
H4 H 0.416724 0.982183 0.561041 0.029 Uiso 1 1 calc R U . . .
C5 C 0.51137(11) 0.6962(3) 0.58869(8) 0.0209(3) Uani 1 1 d . . . . .
C6 C 0.65217(10) 0.5349(3) 0.55997(8) 0.0195(3) Uani 1 1 d . . . . .
C7 C 0.62317(10) 0.3924(3) 0.61459(8) 0.0203(3) Uani 1 1 d . . . . .
C8 C 0.68359(11) 0.1973(3) 0.63900(9) 0.0213(3) Uani 1 1 d . . . . .
H8 H 0.665357 0.096157 0.676069 0.026 Uiso 1 1 calc R U . . .
C9 C 0.77131(11) 0.1573(3) 0.60687(9) 0.0233(4) Uani 1 1 d . . . . .
H9 H 0.813755 0.025602 0.622183 0.028 Uiso 1 1 calc R U . . .
C10 C 0.79879(11) 0.3070(3) 0.55223(9) 0.0222(3) Uani 1 1 d . . . . .
H10 H 0.859917 0.274067 0.532139 0.027 Uiso 1 1 calc R U . . .
C11 C 0.73998(10) 0.5018(3) 0.52637(8) 0.0209(3) Uani 1 1 d . . . . .
C12 C 0.76405(11) 0.6677(3) 0.46735(8) 0.0211(3) Uani 1 1 d . . . . .
H12A H 0.768546 0.831885 0.486725 0.025 Uiso 1 1 calc R U . . .
H12B H 0.706550 0.663274 0.427813 0.025 Uiso 1 1 calc R U . . .
C13 C 0.86281(12) 0.6120(3) 0.43574(10) 0.0277(4) Uani 1 1 d . . . . .
H13A H 0.921047 0.619435 0.474685 0.033 Uiso 1 1 calc R U . . .
H13B H 0.859141 0.447937 0.416248 0.033 Uiso 1 1 calc R U . . .
C14 C 0.88155(11) 0.7834(3) 0.37636(9) 0.0242(4) Uani 1 1 d . . . . .
C15 C 0.83105(11) 0.7550(3) 0.30644(9) 0.0252(4) Uani 1 1 d . . . . .
H15 H 0.786352 0.623746 0.295662 0.030 Uiso 1 1 calc R U . . .
C16 C 0.84570(11) 0.9169(3) 0.25280(9) 0.0253(4) Uani 1 1 d . . . . .
H16 H 0.810246 0.896900 0.205658 0.030 Uiso 1 1 calc R U . . .
C17 C 0.91184(11) 1.1084(3) 0.26731(9) 0.0253(4) Uani 1 1 d . . . . .
H17 H 0.922058 1.218560 0.230303 0.030 Uiso 1 1 calc R U . . .
C18 C 0.96269(11) 1.1369(3) 0.33641(9) 0.0261(4) Uani 1 1 d . . . . .
H18 H 1.008240 1.266732 0.346878 0.031 Uiso 1 1 calc R U . . .
C19 C 0.94715(11) 0.9760(3) 0.39025(9) 0.0253(4) Uani 1 1 d . . . . .
H19 H 0.981991 0.997818 0.437494 0.030 Uiso 1 1 calc R U . . .
N1 N 0.38184(9) 0.6010(2) 0.68909(7) 0.0241(3) Uani 1 1 d . . . . .
O1 O 0.58371(7) 0.72031(18) 0.54212(6) 0.0214(3) Uani 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
-1 0 0 0.0369
-1 3 -4 0.1623
1 -3 4 0.1623
1 0 -5 0.0222
-1 0 5 0.0222
5 0 -2 0.0097
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
C2 C1 C7 136.50(14) . . ?
C5 C1 C2 117.59(13) . . ?
C5 C1 C7 105.91(13) . . ?
C1 C2 H2 119.2 . . ?
N1 C2 C1 121.67(14) . . ?
N1 C2 H2 119.2 . . ?
C4 C3 H3 117.4 . . ?
N1 C3 H3 117.4 . . ?
N1 C3 C4 125.25(14) . . ?
C3 C4 H4 122.8 . . ?
C5 C4 C3 114.32(15) . . ?
C5 C4 H4 122.8 . . ?
C1 C5 C4 122.84(14) . . ?
O1 C5 C1 112.16(12) . . ?
O1 C5 C4 125.00(14) . . ?
C7 C6 C11 125.04(14) . . ?
C7 C6 O1 112.14(12) . . ?
O1 C6 C11 122.82(13) . . ?
C6 C7 C1 104.94(13) . . ?
C6 C7 C8 119.55(13) . . ?
C8 C7 C1 135.50(14) . . ?
C7 C8 H8 121.3 . . ?
C9 C8 C7 117.31(14) . . ?
C9 C8 H8 121.3 . . ?
C8 C9 H9 119.2 . . ?
C8 C9 C10 121.53(14) . . ?
C10 C9 H9 119.2 . . ?
C9 C10 H10 118.7 . . ?
C11 C10 C9 122.60(14) . . ?
C11 C10 H10 118.7 . . ?
C6 C11 C12 120.60(13) . . ?
C10 C11 C6 113.97(14) . . ?
C10 C11 C12 125.43(13) . . ?
C11 C12 H12A 108.5 . . ?
C11 C12 H12B 108.5 . . ?
C11 C12 C13 115.11(12) . . ?
H12A C12 H12B 107.5 . . ?
C13 C12 H12A 108.5 . . ?
C13 C12 H12B 108.5 . . ?
C12 C13 H13A 109.1 . . ?
C12 C13 H13B 109.1 . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 C12 112.28(12) . . ?
C14 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
C15 C14 C13 120.63(15) . . ?
C19 C14 C13 120.98(16) . . ?
C19 C14 C15 118.37(15) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.48(15) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.59(16) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 120.4 . . ?
C18 C17 C16 119.25(15) . . ?
C18 C17 H17 120.4 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 120.09(15) . . ?
C19 C18 H18 120.0 . . ?
C14 C19 H19 119.4 . . ?
C18 C19 C14 121.21(15) . . ?
C18 C19 H19 119.4 . . ?
C2 N1 C3 118.33(13) . . ?
C5 O1 C6 104.83(11) . . ?
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
C1 C2 1.399(2) . ?
C1 C5 1.384(2) . ?
C1 C7 1.4568(19) . ?
C2 H2 0.9500 . ?
C2 N1 1.3407(19) . ?
C3 H3 0.9500 . ?
C3 C4 1.395(2) . ?
C3 N1 1.342(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(2) . ?
C5 O1 1.3772(18) . ?
C6 C7 1.388(2) . ?
C6 C11 1.398(2) . ?
C6 O1 1.3915(17) . ?
C7 C8 1.398(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.388(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.405(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.392(2) . ?
C11 C12 1.508(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.5297(19) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.513(2) . ?
C14 C15 1.398(2) . ?
C14 C19 1.390(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.385(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.391(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.386(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.387(2) . ?
C19 H19 0.9500 . ?
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
C1 C2 N1 C3 0.9(2) . . . . ?
C1 C5 O1 C6 -1.37(16) . . . . ?
C1 C7 C8 C9 -177.73(16) . . . . ?
C2 C1 C5 C4 0.7(2) . . . . ?
C2 C1 C5 O1 179.92(13) . . . . ?
C2 C1 C7 C6 -178.67(17) . . . . ?
C2 C1 C7 C8 -0.3(3) . . . . ?
C3 C4 C5 C1 -0.1(2) . . . . ?
C3 C4 C5 O1 -179.15(14) . . . . ?
C4 C3 N1 C2 -0.1(2) . . . . ?
C4 C5 O1 C6 177.80(15) . . . . ?
C5 C1 C2 N1 -1.1(2) . . . . ?
C5 C1 C7 C6 0.56(16) . . . . ?
C5 C1 C7 C8 178.89(17) . . . . ?
C6 C7 C8 C9 0.4(2) . . . . ?
C6 C11 C12 C13 179.56(14) . . . . ?
C7 C1 C2 N1 178.02(16) . . . . ?
C7 C1 C5 C4 -178.67(14) . . . . ?
C7 C1 C5 O1 0.52(17) . . . . ?
C7 C6 C11 C10 0.3(2) . . . . ?
C7 C6 C11 C12 179.91(14) . . . . ?
C7 C6 O1 C5 1.76(16) . . . . ?
C7 C8 C9 C10 0.3(2) . . . . ?
C8 C9 C10 C11 -0.7(2) . . . . ?
C9 C10 C11 C6 0.4(2) . . . . ?
C9 C10 C11 C12 -179.15(14) . . . . ?
C10 C11 C12 C13 -0.9(2) . . . . ?
C11 C6 C7 C1 177.91(14) . . . . ?
C11 C6 C7 C8 -0.8(2) . . . . ?
C11 C6 O1 C5 -177.62(14) . . . . ?
C11 C12 C13 C14 179.35(13) . . . . ?
C12 C13 C14 C15 -80.01(18) . . . . ?
C12 C13 C14 C19 98.31(17) . . . . ?
C13 C14 C15 C16 177.77(13) . . . . ?
C13 C14 C19 C18 -178.42(13) . . . . ?
C14 C15 C16 C17 0.8(2) . . . . ?
C15 C14 C19 C18 -0.1(2) . . . . ?
C15 C16 C17 C18 -0.4(2) . . . . ?
C16 C17 C18 C19 -0.2(2) . . . . ?
C17 C18 C19 C14 0.5(2) . . . . ?
C19 C14 C15 C16 -0.6(2) . . . . ?
N1 C3 C4 C5 -0.3(2) . . . . ?
O1 C6 C7 C1 -1.45(16) . . . . ?
O1 C6 C7 C8 179.89(13) . . . . ?
O1 C6 C11 C10 179.61(13) . . . . ?
O1 C6 C11 C12 -0.8(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
-0.9982 0.0005 0.0010 0.0575 -0.1004 0.0202
-0.9931 3.0045 -3.9887 0.1850 -0.2511 -0.8452
0.9931 -3.0045 3.9887 -0.1850 0.2511 0.8452
0.9955 0.0011 -4.9984 0.3173 0.2280 -0.1467
-0.9955 -0.0011 4.9984 -0.3173 -0.2280 0.1467
4.9897 -0.0019 -2.0037 -0.1375 0.5532 -0.1516
