#------------------------------------------------------------------------------
#$Date: 2023-04-04 13:00:39 +0300 (Tue, 04 Apr 2023) $
#$Revision: 282293 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/85/1568526.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_1568526
loop_
_publ_author_name
'Finkelstein, Patrick'
'Reisenbauer, Julia C.'
'Botlik, Bence B.'
'Green, Ori'
'Florin, Andri'
'Morandi, Bill'
_publ_section_title
;
 Nitrogen atom insertion into indenes to access isoquinolines.
;
_journal_issue                   11
_journal_name_full               'Chemical science'
_journal_page_first              2954
_journal_page_last               2959
_journal_paper_doi               10.1039/d2sc06952k
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C22 H15 N O'
_chemical_formula_sum            'C22 H15 N O'
_chemical_formula_weight         309.35
_chemical_name_systematic        (4-(isoquinolin-1-yl)phenyl)(phenyl)methanone
_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             2022-11-04
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-11-24 deposited with the CCDC.	2023-02-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.498(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8089(3)
_cell_length_b                   8.7371(2)
_cell_length_c                   18.3869(5)
_cell_measurement_reflns_used    9139
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      78.0250
_cell_measurement_theta_min      5.6340
_cell_volume                     1525.60(7)
_computing_cell_refinement       'CrysAlisPro 1.171.42.61a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.61a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.61a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (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      100.0(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -107.00 -47.00   0.50    0.46    --  -49.37 -76.00 -67.00  120
  2  ω    -63.00  23.00   0.50    0.46    --  -49.37  76.00  58.00  172
  3  ω    -18.00  59.00   0.50    0.46    --   49.37 -76.00 -67.00  154
  4  ω     51.00  76.00   0.50    0.46    --   49.37  76.00  58.00   50
  5  ω    -84.00 -59.00   0.50    1.38    --  -90.00  76.00  58.00   50
  6  ω   -106.00 -80.00   0.50    1.38    --  -90.00 -76.00 -67.00   52
  7  ω     91.00 177.00   0.50    1.38    --  111.50  76.00  58.00  172
  8  ω     42.00  91.00   0.50    1.38    --  111.50 -76.00 -67.00   98
  9  ω   -107.00 -81.00   0.50    0.46    --  -49.37-125.00-180.00   52
 10  ω   -112.00 -74.00   0.50    0.46    --  -49.37-125.00  90.00   76
 11  ω    -15.00  22.00   0.50    0.46    --  -49.37  19.00  60.00   74
 12  ω   -141.00 -86.00   0.50    1.38    --  -90.00 -30.00 150.00  110
 13  ω    -51.00 -26.00   0.50    1.38    --  -90.00  45.00-120.00   50
 14  ω   -137.00 -96.00   0.50    1.38    --  -90.00 -15.00-180.00   82
 15  ω    -51.00 -26.00   0.50    1.38    --  -90.00  45.00 -90.00   50
 16  ω    141.00 171.00   0.50    1.38    --  111.50  61.00 150.00   60
 17  ω     98.00 133.00   0.50    1.38    --  111.50  61.00 150.00   70
 18  ω    105.00 150.00   0.50    1.38    --  111.50  30.00 -30.00   90
 19  ω     85.00 111.00   0.50    1.38    --  111.50-125.00  30.00   52
 20  ω    104.00 156.00   0.50    1.38    --  111.50  15.00-180.00  104
 21  ω     97.00 129.00   0.50    1.38    --  111.50  77.00  90.00   64
 22  ω     41.00 105.00   0.50    1.38    --  111.50 -95.00-180.00  128
 23  ω     43.00  68.00   0.50    1.38    --  111.50-125.00  30.00   50
 24  ω     45.00  91.00   0.50    1.38    --  111.50-125.00  60.00   92
 25  ω    104.00 177.00   0.50    1.38    --  111.50  77.00  30.00  146
 26  ω    110.00 165.00   0.50    1.38    --  111.50  30.00-150.00  110
 27  ω     41.00  67.00   0.50    1.38    --  111.50 -95.00   0.00   52
 28  ω     45.00 100.00   0.50    1.38    --  111.50 -95.00 120.00  110
 29  ω     41.00  66.00   0.50    1.38    --  111.50 -61.00-150.00   50
 30  ω     76.00 101.00   0.50    1.38    --  111.50-125.00 -30.00   50
 31  ω     41.00 102.00   0.50    1.38    --  111.50 -77.00-150.00  122
 32  ω     98.00 161.00   0.50    1.38    --  111.50  61.00   0.00  126
 33  ω    104.00 138.00   0.50    1.38    --  111.50  30.00-120.00   68
 34  ω    105.00 151.00   0.50    1.38    --  111.50 125.00  90.00   92
 35  ω     41.00  66.00   0.50    1.38    --  111.50 -61.00 -30.00   50
 36  ω    103.00 176.00   0.50    1.38    --  111.50  61.00  90.00  146
 37  ω     42.00  83.00   0.50    1.38    --  111.50 -77.00-180.00   82
 38  ω     71.00  99.00   0.50    1.38    --  111.50 -77.00  30.00   56
 39  ω    104.00 149.00   0.50    1.38    --  111.50  45.00 150.00   90
 40  ω     45.00 108.00   0.50    1.38    --  111.50-125.00  90.00  126
 41  ω     93.00 151.00   0.50    1.38    --  111.50  77.00 -30.00  116
 42  ω     46.00  79.00   0.50    1.38    --  111.50 -77.00-120.00   66
 43  ω    105.00 177.00   0.50    1.38    --  111.50 125.00 150.00  144
 44  ω     42.00  84.00   0.50    1.38    --  111.50 -95.00  30.00   84
 45  ω     43.00  68.00   0.50    1.38    --  111.50 -61.00  60.00   50
;
_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      0.0882562000
_diffrn_orient_matrix_UB_12      0.1462508000
_diffrn_orient_matrix_UB_13      0.0010885000
_diffrn_orient_matrix_UB_21      0.0520146000
_diffrn_orient_matrix_UB_22      -0.0113575000
_diffrn_orient_matrix_UB_23      0.0861297000
_diffrn_orient_matrix_UB_31      0.1257302000
_diffrn_orient_matrix_UB_32      -0.0978655000
_diffrn_orient_matrix_UB_33      -0.0084711000
_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  0.0557
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            21147
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.327
_diffrn_reflns_theta_min         4.656
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.646
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.717
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.61a (Rigaku Oxford Diffraction, 2022)
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 light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_description       plate
_exptl_crystal_F_000             648
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl acetate and hexane'
_exptl_crystal_size_max          0.154
_exptl_crystal_size_mid          0.133
_exptl_crystal_size_min          0.058
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3303
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.143
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0752
_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)+(0.1215P)²+2.2451P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2394
_refine_ls_wR_factor_ref         0.2429
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2943
_reflns_number_total             3303
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc06952k2.cif
_cod_data_source_block           bm041122_1_1
_cod_depositor_comments
'Adding full bibliography for 1568525--1568526.cif.'
_cod_database_code               1568526
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_chemical_oxdiff_usercomment
'yellow plate, from Py/Et2O at -35 degree Celsius.'
_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   0.962
_shelx_estimated_absorpt_t_min   0.909
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13),
 C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21)
;
_olex2_date_sample_data_collection 2022-11-02
_olex2_date_sample_submission    2022-11-02
_olex2_submission_original_sample_id bm041122_1_1
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.635
_oxdiff_exptl_absorpt_empirical_full_min 0.748
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 0.9724(2) 0.5278(2) 0.59701(11) 0.0299(5) Uani 1 1 d . . . . .
N1 N 0.3051(2) 0.5907(3) 0.31666(13) 0.0263(5) Uani 1 1 d . . . . .
C1 C 0.8923(3) 0.4383(3) 0.55555(15) 0.0246(5) Uani 1 1 d . . . . .
C2 C 0.9190(3) 0.2702(3) 0.56167(14) 0.0233(5) Uani 1 1 d . . . . .
C3 C 1.0550(3) 0.2177(3) 0.59537(15) 0.0272(6) Uani 1 1 d . . . . .
H3 H 1.130394 0.288480 0.610155 0.033 Uiso 1 1 calc R U . . .
C4 C 1.0794(3) 0.0621(3) 0.60714(16) 0.0304(6) Uani 1 1 d . . . . .
H4 H 1.171984 0.026466 0.629284 0.036 Uiso 1 1 calc R U . . .
C5 C 0.9695(3) -0.0417(3) 0.58679(16) 0.0307(6) Uani 1 1 d . . . . .
H5 H 0.986576 -0.147830 0.595898 0.037 Uiso 1 1 calc R U . . .
C6 C 0.8342(3) 0.0095(3) 0.55306(16) 0.0298(6) Uani 1 1 d . . . . .
H6 H 0.758905 -0.061590 0.538964 0.036 Uiso 1 1 calc R U . . .
C7 C 0.8093(3) 0.1651(3) 0.54000(15) 0.0253(6) Uani 1 1 d . . . . .
H7 H 0.717155 0.199846 0.516212 0.030 Uiso 1 1 calc R U . . .
C8 C 0.7642(3) 0.4984(3) 0.50072(15) 0.0238(6) Uani 1 1 d . . . . .
C9 C 0.7184(3) 0.4420(3) 0.42762(15) 0.0246(5) Uani 1 1 d . . . . .
H9 H 0.766990 0.359330 0.411849 0.030 Uiso 1 1 calc R U . . .
C10 C 0.6021(3) 0.5060(3) 0.37780(15) 0.0244(6) Uani 1 1 d . . . . .
H10 H 0.570905 0.465948 0.328393 0.029 Uiso 1 1 calc R U . . .
C11 C 0.5305(3) 0.6290(3) 0.39986(15) 0.0240(5) Uani 1 1 d . . . . .
C12 C 0.5774(3) 0.6851(3) 0.47312(16) 0.0257(6) Uani 1 1 d . . . . .
H12 H 0.529375 0.768350 0.488876 0.031 Uiso 1 1 calc R U . . .
C13 C 0.6928(3) 0.6210(3) 0.52300(15) 0.0243(5) Uani 1 1 d . . . . .
H13 H 0.723576 0.660559 0.572536 0.029 Uiso 1 1 calc R U . . .
C14 C 0.4030(3) 0.6924(3) 0.34653(15) 0.0238(5) Uani 1 1 d . . . . .
C15 C 0.1826(3) 0.6429(3) 0.27103(15) 0.0288(6) Uani 1 1 d . . . . .
H15 H 0.112579 0.569589 0.249549 0.035 Uiso 1 1 calc R U . . .
C16 C 0.1534(3) 0.7933(3) 0.25401(15) 0.0291(6) Uani 1 1 d . . . . .
H16 H 0.064866 0.823032 0.222746 0.035 Uiso 1 1 calc R U . . .
C17 C 0.2577(3) 0.9041(3) 0.28384(15) 0.0265(6) Uani 1 1 d . . . . .
C18 C 0.2363(3) 1.0631(3) 0.26875(16) 0.0299(6) Uani 1 1 d . . . . .
H18 H 0.148865 1.098118 0.238212 0.036 Uiso 1 1 calc R U . . .
C19 C 0.3406(3) 1.1659(3) 0.29791(17) 0.0336(7) Uani 1 1 d . . . . .
H19 H 0.324853 1.272102 0.288223 0.040 Uiso 1 1 calc R U . . .
C20 C 0.4715(3) 1.1151(3) 0.34233(18) 0.0345(7) Uani 1 1 d . . . . .
H20 H 0.544415 1.187118 0.361122 0.041 Uiso 1 1 calc R U . . .
C21 C 0.4947(3) 0.9623(3) 0.35867(17) 0.0295(6) Uani 1 1 d . . . . .
H21 H 0.583204 0.929580 0.388854 0.035 Uiso 1 1 calc R U . . .
C22 C 0.3872(3) 0.8530(3) 0.33075(15) 0.0246(6) 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
0 0 -1 0.0286
0 0 1 0.0296
6 0 -4 0.0625
-6 -1 4 0.0681
-1 6 1 0.0793
6 1 -1 0.0584
-1 5 5 0.0681
5 -4 -4 0.0798
4 1 6 0.0455
1 3 9 0.0475
-6 2 1 0.0778
4 -2 7 0.0593
-5 3 2 0.0742
-3 4 -5 0.0625
2 -3 8 0.0574
-5 -2 9 0.0592
2 -5 4 0.0628
-4 5 0 0.0633
1 -6 1 0.0614
-5 -3 5 0.0736
-4 -4 0 0.0792
0 -6 -3 0.0623
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
C14 N1 C15 117.9(2) . . ?
O1 C1 C2 120.5(2) . . ?
O1 C1 C8 119.6(2) . . ?
C2 C1 C8 119.9(2) . . ?
C3 C2 C1 119.0(2) . . ?
C7 C2 C1 121.3(2) . . ?
C7 C2 C3 119.5(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.1(3) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 H6 120.1 . . ?
C5 C6 C7 119.9(3) . . ?
C7 C6 H6 120.1 . . ?
C2 C7 H7 119.8 . . ?
C6 C7 C2 120.3(3) . . ?
C6 C7 H7 119.8 . . ?
C9 C8 C1 122.6(2) . . ?
C13 C8 C1 118.0(2) . . ?
C13 C8 C9 119.3(2) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.4(2) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.5(2) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C12 118.8(2) . . ?
C10 C11 C14 119.6(2) . . ?
C12 C11 C14 121.5(2) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.9(2) . . ?
C13 C12 H12 119.6 . . ?
C8 C13 H13 119.9 . . ?
C12 C13 C8 120.2(2) . . ?
C12 C13 H13 119.9 . . ?
N1 C14 C11 115.3(2) . . ?
N1 C14 C22 122.9(2) . . ?
C22 C14 C11 121.8(2) . . ?
N1 C15 H15 117.8 . . ?
N1 C15 C16 124.5(3) . . ?
C16 C15 H15 117.8 . . ?
C15 C16 H16 120.7 . . ?
C15 C16 C17 118.7(3) . . ?
C17 C16 H16 120.7 . . ?
C16 C17 C18 122.4(3) . . ?
C16 C17 C22 118.1(2) . . ?
C22 C17 C18 119.5(3) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.4(3) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.3(3) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 119.7 . . ?
C21 C20 C19 120.6(3) . . ?
C21 C20 H20 119.7 . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.5(3) . . ?
C22 C21 H21 119.8 . . ?
C17 C22 C14 117.8(2) . . ?
C17 C22 C21 118.7(2) . . ?
C21 C22 C14 123.5(2) . . ?
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 C1 1.228(3) . ?
N1 C14 1.322(3) . ?
N1 C15 1.361(4) . ?
C1 C2 1.492(3) . ?
C1 C8 1.496(4) . ?
C2 C3 1.400(4) . ?
C2 C7 1.395(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.388(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.387(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.390(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.391(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.396(4) . ?
C8 C13 1.396(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.389(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.398(4) . ?
C11 C12 1.399(4) . ?
C11 C14 1.490(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.385(4) . ?
C13 H13 0.9500 . ?
C14 C22 1.434(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.364(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.415(4) . ?
C17 C18 1.422(4) . ?
C17 C22 1.417(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.366(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.410(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.375(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.420(4) . ?
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 C1 C2 C3 -21.1(4) . . . . ?
O1 C1 C2 C7 153.8(3) . . . . ?
O1 C1 C8 C9 139.6(3) . . . . ?
O1 C1 C8 C13 -37.1(4) . . . . ?
N1 C14 C22 C17 3.1(4) . . . . ?
N1 C14 C22 C21 -175.9(3) . . . . ?
N1 C15 C16 C17 1.6(4) . . . . ?
C1 C2 C3 C4 174.7(2) . . . . ?
C1 C2 C7 C6 -173.6(2) . . . . ?
C1 C8 C9 C10 -177.3(2) . . . . ?
C1 C8 C13 C12 177.1(2) . . . . ?
C2 C1 C8 C9 -42.8(4) . . . . ?
C2 C1 C8 C13 140.5(3) . . . . ?
C2 C3 C4 C5 -1.0(4) . . . . ?
C3 C2 C7 C6 1.2(4) . . . . ?
C3 C4 C5 C6 1.2(4) . . . . ?
C4 C5 C6 C7 -0.2(4) . . . . ?
C5 C6 C7 C2 -1.0(4) . . . . ?
C7 C2 C3 C4 -0.2(4) . . . . ?
C8 C1 C2 C3 161.3(2) . . . . ?
C8 C1 C2 C7 -23.8(4) . . . . ?
C8 C9 C10 C11 0.8(4) . . . . ?
C9 C8 C13 C12 0.3(4) . . . . ?
C9 C10 C11 C12 -0.7(4) . . . . ?
C9 C10 C11 C14 -177.8(2) . . . . ?
C10 C11 C12 C13 0.3(4) . . . . ?
C10 C11 C14 N1 52.1(3) . . . . ?
C10 C11 C14 C22 -129.5(3) . . . . ?
C11 C12 C13 C8 -0.2(4) . . . . ?
C11 C14 C22 C17 -175.2(2) . . . . ?
C11 C14 C22 C21 5.7(4) . . . . ?
C12 C11 C14 N1 -125.0(3) . . . . ?
C12 C11 C14 C22 53.5(4) . . . . ?
C13 C8 C9 C10 -0.7(4) . . . . ?
C14 N1 C15 C16 -0.2(4) . . . . ?
C14 C11 C12 C13 177.4(2) . . . . ?
C15 N1 C14 C11 176.1(2) . . . . ?
C15 N1 C14 C22 -2.3(4) . . . . ?
C15 C16 C17 C18 179.8(3) . . . . ?
C15 C16 C17 C22 -0.6(4) . . . . ?
C16 C17 C18 C19 -179.1(3) . . . . ?
C16 C17 C22 C14 -1.5(4) . . . . ?
C16 C17 C22 C21 177.6(3) . . . . ?
C17 C18 C19 C20 1.0(4) . . . . ?
C18 C17 C22 C14 178.0(2) . . . . ?
C18 C17 C22 C21 -2.8(4) . . . . ?
C18 C19 C20 C21 -1.9(5) . . . . ?
C19 C20 C21 C22 0.3(5) . . . . ?
C20 C21 C22 C14 -178.9(3) . . . . ?
C20 C21 C22 C17 2.0(4) . . . . ?
C22 C17 C18 C19 1.3(4) . . . . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0015 -0.0010 -1.0014 -0.0011 -0.0862 0.0088
-0.0016 0.0008 1.0020 0.0011 0.0862 -0.0088
6.3466 0.2086 -3.9798 0.5863 -0.0150 0.8113
-6.3261 -0.5630 3.9604 -0.6363 0.0185 -0.7738
-0.9479 5.6017 1.1110 0.7368 -0.0172 -0.6768
6.1974 0.6466 -0.5749 0.6409 0.2655 0.7208
-0.6642 5.2335 4.5651 0.7117 0.2992 -0.6344
4.6329 -3.7800 -4.0290 -0.1483 -0.0631 0.9866
4.4533 1.0858 5.9043 0.5583 0.7278 0.4036
1.0090 3.3232 8.7170 0.5846 0.7655 -0.2722
-5.8184 2.0913 0.7028 -0.2069 -0.2659 -0.9422
3.8357 -1.6170 6.8276 0.1095 0.8059 0.5827
-5.3595 3.0424 1.8061 -0.0261 -0.1578 -0.9869
-2.9770 3.6992 -5.4900 0.2723 -0.6697 -0.6898
1.7777 -3.3912 7.8515 -0.3305 0.8072 0.4889
-4.5398 -1.6582 9.4516 -0.6329 0.5968 -0.4886
1.6731 -4.8197 4.4950 -0.5523 0.5289 0.6440
-3.6955 4.5236 -0.2247 0.3352 -0.2629 -0.9054
0.8191 -5.5908 0.8682 -0.7444 0.1809 0.6428
-4.8785 -3.3748 5.0269 -0.9187 0.2175 -0.3257
-4.0183 -4.2684 -0.2702 -0.9792 -0.1838 -0.0852
0.4337 -5.5372 -2.6303 -0.7744 -0.1411 0.6187
