#------------------------------------------------------------------------------
#$Date: 2024-12-06 18:44:13 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296398 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/24/1572486.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_1572486
loop_
_publ_author_name
'Cai, Heng'
'Tu, Yong-Qiang'
'Niu, Qiang'
'Xie, Wen-Ping'
'Wang, Bin'
'Lu, Ka'
'Li, Zi-Hao'
'Zhang, Fu-Min'
'Zhang, Xiao-Ming'
_publ_section_title
;
 CCC pincer Ru complex-catalyzed C-H vinylation/6π-E-cyclization of
 aldimines for constructing 4H-pyrido[1,2-a]pyrimidines.
;
_journal_issue                   39
_journal_name_full               'Chemical science'
_journal_page_first              16216
_journal_page_last               16221
_journal_paper_doi               10.1039/d4sc05067c
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C20 H22 N2'
_chemical_formula_sum            'C20 H22 N2'
_chemical_formula_weight         290.39
_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             2023-08-03
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2024-03-18 deposited with the CCDC.	2024-09-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.3230(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.1803(2)
_cell_length_b                   12.0750(2)
_cell_length_c                   28.1968(4)
_cell_measurement_reflns_used    8230
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      76.4180
_cell_measurement_theta_min      3.1580
_cell_volume                     3106.66(10)
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -89.00 -63.00   1.00    0.50    --  -44.30 146.00 135.00   26
  2  ω   -126.00 -76.00   1.00    1.50    -- -100.00 146.00 135.00   50
  3  ω    -60.00 -35.00   1.00    1.50    -- -100.00 146.00 135.00   25
  4  ω   -112.00 -29.00   1.00    1.50    -- -100.00 125.00 120.00   83
  5  ω    -76.00 -29.00   1.00    1.50    -- -100.00 125.00   0.00   47
  6  ω   -103.00 -77.00   1.00    1.50    -- -100.00 124.00 -30.00   26
  7  ω    -90.00 -36.00   1.00    0.50    --  -44.30 124.00 -30.00   54
  8  ω    -51.00 -25.00   1.00    1.50    -- -100.00  45.00-180.00   26
  9  ω    -71.00 -30.00   1.00    1.50    -- -100.00  61.00-150.00   41
 10  ω    -52.00 -26.00   1.00    1.50    -- -100.00  45.00-150.00   26
 11  ω     68.00  94.00   1.00    1.50    --  109.64-124.00-108.00   26
 12  ω    -53.00 -26.00   1.00    1.50    -- -100.00  45.00 150.00   27
 13  ω    -53.00 -25.00   1.00    1.50    -- -100.00  45.00 120.00   28
 14  ω   -154.00 -97.00   1.00    1.50    -- -100.00-124.00-108.00   57
 15  ω   -121.00 -82.00   1.00    1.50    -- -100.00-125.00-150.00   39
 16  ω   -170.00-130.00   1.00    1.50    -- -100.00-125.00-150.00   40
 17  ω   -105.00 -78.00   1.00    0.50    --  -44.30-146.00  85.00   27
 18  ω    -19.00  20.00   1.00    0.50    --   44.30 -19.00 -30.00   39
 19  ω    -33.00  23.00   1.00    0.50    --   44.30 -19.00-120.00   56
 20  ω     -9.00  24.00   1.00    0.50    --   44.30 -19.00-180.00   33
 21  ω    -34.00  23.00   1.00    0.50    --   44.30 -19.00 120.00   57
 22  ω     42.00  67.00   1.00    1.50    --  109.64 -61.00 -90.00   25
 23  ω     67.00 101.00   1.00    1.50    --  109.64 -77.00-120.00   34
 24  ω     41.00  68.00   1.00    1.50    --  109.64 -61.00-120.00   27
 25  ω     38.00  67.00   1.00    1.50    --  109.64 -61.00 -60.00   29
 26  ω    112.00 137.00   1.00    1.50    --  109.64  30.00  60.00   25
 27  ω    150.00 175.00   1.00    1.50    --  109.64  30.00  60.00   25
 28  ω    110.00 148.00   1.00    1.50    --  109.64  30.00 -60.00   38
 29  ω     78.00 138.00   1.00    1.50    --  109.64 124.00 -30.00   60
;
_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      0.0238818000
_diffrn_orient_matrix_UB_12      -0.0449158000
_diffrn_orient_matrix_UB_13      -0.0497262000
_diffrn_orient_matrix_UB_21      -0.0051224000
_diffrn_orient_matrix_UB_22      0.1190531000
_diffrn_orient_matrix_UB_23      -0.0198098000
_diffrn_orient_matrix_UB_31      0.1669276000
_diffrn_orient_matrix_UB_32      0.0100730000
_diffrn_orient_matrix_UB_33      0.0126056000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            6789
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.613
_diffrn_reflns_theta_min         3.154
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.556
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58481
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     400
_refine_ls_number_reflns         6789
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0647
_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)+(0.0997P)²+2.2943P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1855
_refine_ls_wR_factor_ref         0.1892
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6160
_reflns_number_total             6789
_reflns_threshold_expression     'I > 2σ(I)'
_twin_special_details
;
Component 2 rotated by 179.9528° 
around [0.95 -0.00 -0.32] (reciprocal) or [1.00 -0.00 -0.00] (direct)
;
_cod_data_source_file            d4sc05067c2.cif
_cod_data_source_block           caihen_0803_twin1_hklf4
_cod_depositor_comments
'Adding full bibliography for 1572486--1572491.cif.'
_cod_database_code               1572486
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_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.
;
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.652(2)
 0.348(2)
2. 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
3.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,
 H14B), C30(H30A,H30B), C31(H31A,H31B), C32(H32A,H32B), C33(H33A,H33B),
 C34(H34A,H34B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C8(H8), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20), C22(H22), C23(H23), C24(H24), C28(H28), C36(H36), C37(H37), C38(H38),
  C39(H39), C40(H40)
3.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C26(H26A,H26B,H26C)
;
_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 1.849
_oxdiff_exptl_absorpt_empirical_full_min 0.582
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
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
N001 N 0.9990(3) 0.45144(19) 0.81813(8) 0.0283(5) Uani 1 1 d . . . . .
N002 N 0.8275(2) 0.30144(18) 0.80926(7) 0.0261(5) Uani 1 1 d . . . . .
C1 C 0.7327(3) 0.2388(2) 0.77863(10) 0.0315(6) Uani 1 1 d . . . . .
H1 H 0.678967 0.180857 0.791471 0.038 Uiso 1 1 calc R U . . .
C2 C 0.7137(3) 0.2569(2) 0.73136(10) 0.0340(6) Uani 1 1 d . . . . .
H2 H 0.648103 0.212154 0.711188 0.041 Uiso 1 1 calc R U . . .
C3 C 0.7929(3) 0.3434(2) 0.71195(9) 0.0312(6) Uani 1 1 d . . . . .
H3 H 0.779299 0.357414 0.678597 0.037 Uiso 1 1 calc R U . . .
C4 C 0.8883(3) 0.4067(2) 0.74074(9) 0.0272(5) Uani 1 1 d . . . . .
C5 C 0.9063(3) 0.3882(2) 0.79157(9) 0.0253(5) Uani 1 1 d . . . . .
C6 C 0.9789(3) 0.4957(2) 0.72166(9) 0.0327(6) Uani 1 1 d . . . . .
H6A H 1.081352 0.471583 0.723783 0.049 Uiso 1 1 calc R U . . .
H6B H 0.971986 0.563382 0.740435 0.049 Uiso 1 1 calc R U . . .
H6C H 0.942777 0.510347 0.688240 0.049 Uiso 1 1 calc R U . . .
C7 C 1.0312(3) 0.4221(2) 0.86551(9) 0.0248(5) Uani 1 1 d . . . . .
C8 C 0.9582(3) 0.3432(2) 0.88671(9) 0.0282(6) Uani 1 1 d . . . . .
H8 H 0.992597 0.321882 0.918408 0.034 Uiso 1 1 calc R U . . .
C9 C 0.8240(3) 0.2872(2) 0.86226(9) 0.0258(5) Uani 1 1 d . . . . .
C10 C 0.8237(3) 0.1637(2) 0.87628(9) 0.0303(6) Uani 1 1 d . . . . .
H10A H 0.740775 0.125887 0.857462 0.036 Uiso 1 1 calc R U . . .
H10B H 0.915650 0.128603 0.868581 0.036 Uiso 1 1 calc R U . . .
C11 C 0.8098(3) 0.1493(2) 0.92972(10) 0.0338(6) Uani 1 1 d . . . . .
H11A H 0.803343 0.069426 0.937057 0.041 Uiso 1 1 calc R U . . .
H11B H 0.898813 0.179087 0.948410 0.041 Uiso 1 1 calc R U . . .
C12 C 0.6754(4) 0.2083(2) 0.94474(10) 0.0373(7) Uani 1 1 d . . . . .
H12A H 0.585742 0.170309 0.930279 0.045 Uiso 1 1 calc R U . . .
H12B H 0.676978 0.204059 0.979859 0.045 Uiso 1 1 calc R U . . .
C13 C 0.6703(3) 0.3293(2) 0.92944(10) 0.0337(6) Uani 1 1 d . . . . .
H13A H 0.751657 0.369907 0.947747 0.040 Uiso 1 1 calc R U . . .
H13B H 0.577000 0.362620 0.936908 0.040 Uiso 1 1 calc R U . . .
C14 C 0.6828(3) 0.3417(2) 0.87615(9) 0.0292(6) Uani 1 1 d . . . . .
H14A H 0.682916 0.421290 0.867798 0.035 Uiso 1 1 calc R U . . .
H14B H 0.596712 0.306885 0.857762 0.035 Uiso 1 1 calc R U . . .
C15 C 1.1571(3) 0.4837(2) 0.89118(9) 0.0263(5) Uani 1 1 d . . . . .
C16 C 1.2161(3) 0.5743(2) 0.86909(10) 0.0318(6) Uani 1 1 d . . . . .
H16 H 1.179278 0.593604 0.837360 0.038 Uiso 1 1 calc R U . . .
C17 C 1.3284(3) 0.6364(3) 0.89331(11) 0.0377(7) Uani 1 1 d . . . . .
H17 H 1.368166 0.697581 0.877926 0.045 Uiso 1 1 calc R U . . .
C18 C 1.3823(3) 0.6098(2) 0.93932(10) 0.0342(6) Uani 1 1 d . . . . .
H18 H 1.457329 0.653656 0.955923 0.041 Uiso 1 1 calc R U . . .
C19 C 1.3268(3) 0.5189(2) 0.96147(10) 0.0332(6) Uani 1 1 d . . . . .
H19 H 1.365509 0.498968 0.992944 0.040 Uiso 1 1 calc R U . . .
C20 C 1.2146(3) 0.4573(2) 0.93742(9) 0.0302(6) Uani 1 1 d . . . . .
H20 H 1.176248 0.395637 0.952904 0.036 Uiso 1 1 calc R U . . .
N003 N 0.2876(2) 0.29973(19) 0.68532(8) 0.0281(5) Uani 1 1 d . . . . .
N004 N 0.4515(3) 0.45110(19) 0.67764(8) 0.0285(5) Uani 1 1 d . . . . .
C21 C 0.3905(3) 0.4048(2) 0.75457(9) 0.0285(6) Uani 1 1 d . . . . .
C22 C 0.3164(3) 0.3400(3) 0.78295(10) 0.0344(6) Uani 1 1 d . . . . .
H22 H 0.324939 0.353158 0.816357 0.041 Uiso 1 1 calc R U . . .
C23 C 0.2264(4) 0.2530(3) 0.76307(10) 0.0386(7) Uani 1 1 d . . . . .
H23 H 0.174868 0.207309 0.783016 0.046 Uiso 1 1 calc R U . . .
C24 C 0.2144(3) 0.2353(2) 0.71577(10) 0.0346(6) Uani 1 1 d . . . . .
H24 H 0.153680 0.176663 0.702736 0.041 Uiso 1 1 calc R U . . .
C25 C 0.3761(3) 0.3867(2) 0.70362(9) 0.0261(5) Uani 1 1 d . . . . .
C26 C 0.4927(3) 0.4953(2) 0.77420(10) 0.0337(6) Uani 1 1 d . . . . .
H26A H 0.594166 0.473311 0.771489 0.051 Uiso 1 1 calc R U . . .
H26B H 0.479954 0.508008 0.807822 0.051 Uiso 1 1 calc R U . . .
H26C H 0.470366 0.563610 0.756052 0.051 Uiso 1 1 calc R U . . .
C27 C 0.4558(3) 0.4221(2) 0.63039(9) 0.0263(5) Uani 1 1 d . . . . .
C28 C 0.3696(3) 0.3433(2) 0.60852(9) 0.0293(6) Uani 1 1 d . . . . .
H28 H 0.384654 0.321878 0.577017 0.035 Uiso 1 1 calc R U . . .
C29 C 0.2500(3) 0.2879(2) 0.63222(9) 0.0261(5) Uani 1 1 d . . . . .
C30 C 0.1002(3) 0.3431(2) 0.61837(9) 0.0297(6) Uani 1 1 d . . . . .
H30A H 0.026774 0.309212 0.637158 0.036 Uiso 1 1 calc R U . . .
H30B H 0.107171 0.422731 0.626578 0.036 Uiso 1 1 calc R U . . .
C31 C 0.0481(3) 0.3309(2) 0.56520(10) 0.0327(6) Uani 1 1 d . . . . .
H31A H -0.050008 0.364903 0.558228 0.039 Uiso 1 1 calc R U . . .
H31B H 0.116517 0.370435 0.546281 0.039 Uiso 1 1 calc R U . . .
C32 C 0.0407(3) 0.2089(2) 0.55078(10) 0.0357(6) Uani 1 1 d . . . . .
H32A H -0.036560 0.171547 0.566780 0.043 Uiso 1 1 calc R U . . .
H32B H 0.013848 0.203115 0.515888 0.043 Uiso 1 1 calc R U . . .
C33 C 0.1857(3) 0.1510(2) 0.56414(10) 0.0357(6) Uani 1 1 d . . . . .
H33A H 0.260143 0.182044 0.545017 0.043 Uiso 1 1 calc R U . . .
H33B H 0.174827 0.071189 0.556423 0.043 Uiso 1 1 calc R U . . .
C34 C 0.2385(3) 0.1642(2) 0.61728(10) 0.0317(6) Uani 1 1 d . . . . .
H34A H 0.335632 0.128688 0.624253 0.038 Uiso 1 1 calc R U . . .
H34B H 0.169298 0.126021 0.636349 0.038 Uiso 1 1 calc R U . . .
C35 C 0.5662(3) 0.4859(2) 0.60615(9) 0.0270(5) Uani 1 1 d . . . . .
C36 C 0.5957(3) 0.4627(2) 0.55987(10) 0.0358(6) Uani 1 1 d . . . . .
H36 H 0.548718 0.401644 0.543331 0.043 Uiso 1 1 calc R U . . .
C37 C 0.6927(4) 0.5272(3) 0.53752(11) 0.0395(7) Uani 1 1 d . . . . .
H37 H 0.712247 0.509596 0.506003 0.047 Uiso 1 1 calc R U . . .
C38 C 0.7611(3) 0.6170(3) 0.56087(11) 0.0378(7) Uani 1 1 d . . . . .
H38 H 0.825064 0.662559 0.545115 0.045 Uiso 1 1 calc R U . . .
C39 C 0.7359(4) 0.6400(3) 0.60705(11) 0.0395(7) Uani 1 1 d . . . . .
H39 H 0.784681 0.700318 0.623551 0.047 Uiso 1 1 calc R U . . .
C40 C 0.6389(3) 0.5749(2) 0.62969(10) 0.0333(6) Uani 1 1 d . . . . .
H40 H 0.622164 0.591467 0.661578 0.040 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'
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 N001 C7 117.2(2) . . ?
C1 N002 C5 120.2(2) . . ?
C1 N002 C9 118.4(2) . . ?
C5 N002 C9 120.5(2) . . ?
N002 C1 H1 118.8 . . ?
C2 C1 N002 122.3(3) . . ?
C2 C1 H1 118.8 . . ?
C1 C2 H2 120.4 . . ?
C1 C2 C3 119.2(3) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.5(2) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 120.1(2) . . ?
C3 C4 C6 122.4(2) . . ?
C5 C4 C6 117.5(2) . . ?
N001 C5 N002 124.1(2) . . ?
N001 C5 C4 118.2(2) . . ?
N002 C5 C4 117.7(2) . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N001 C7 C15 114.4(2) . . ?
C8 C7 N001 123.2(2) . . ?
C8 C7 C15 122.4(2) . . ?
C7 C8 H8 118.7 . . ?
C7 C8 C9 122.6(2) . . ?
C9 C8 H8 118.7 . . ?
N002 C9 C10 111.4(2) . . ?
N002 C9 C14 108.3(2) . . ?
C8 C9 N002 107.3(2) . . ?
C8 C9 C10 110.0(2) . . ?
C8 C9 C14 111.1(2) . . ?
C14 C9 C10 108.8(2) . . ?
C9 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C11 C10 C9 111.3(2) . . ?
C11 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
C10 C11 H11A 109.2 . . ?
C10 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C12 C11 C10 112.1(2) . . ?
C12 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
C11 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
C13 C12 C11 111.7(2) . . ?
C13 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
C12 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
C12 C13 C14 111.7(2) . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C9 C14 H14A 109.4 . . ?
C9 C14 H14B 109.4 . . ?
C13 C14 C9 111.4(2) . . ?
C13 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C16 C15 C7 119.4(2) . . ?
C20 C15 C7 122.3(2) . . ?
C20 C15 C16 118.2(2) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.4(3) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.5(3) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 120.1 . . ?
C17 C18 C19 119.8(3) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 120.2 . . ?
C20 C19 C18 119.7(3) . . ?
C20 C19 H19 120.2 . . ?
C15 C20 H20 119.3 . . ?
C19 C20 C15 121.4(3) . . ?
C19 C20 H20 119.3 . . ?
C24 N003 C25 119.8(2) . . ?
C24 N003 C29 119.3(2) . . ?
C25 N003 C29 120.0(2) . . ?
C25 N004 C27 117.4(2) . . ?
C22 C21 C25 120.2(3) . . ?
C22 C21 C26 122.3(2) . . ?
C25 C21 C26 117.4(2) . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C23 120.3(3) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 H23 120.3 . . ?
C24 C23 C22 119.5(3) . . ?
C24 C23 H23 120.3 . . ?
N003 C24 H24 118.9 . . ?
C23 C24 N003 122.3(3) . . ?
C23 C24 H24 118.9 . . ?
N003 C25 C21 118.0(2) . . ?
N004 C25 N003 124.1(2) . . ?
N004 C25 C21 117.9(2) . . ?
C21 C26 H26A 109.5 . . ?
C21 C26 H26B 109.5 . . ?
C21 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N004 C27 C35 113.8(2) . . ?
C28 C27 N004 122.9(2) . . ?
C28 C27 C35 123.3(2) . . ?
C27 C28 H28 118.9 . . ?
C27 C28 C29 122.2(2) . . ?
C29 C28 H28 118.9 . . ?
N003 C29 C30 108.2(2) . . ?
N003 C29 C34 111.2(2) . . ?
C28 C29 N003 107.5(2) . . ?
C28 C29 C30 111.8(2) . . ?
C28 C29 C34 109.8(2) . . ?
C30 C29 C34 108.3(2) . . ?
C29 C30 H30A 109.1 . . ?
C29 C30 H30B 109.1 . . ?
H30A C30 H30B 107.9 . . ?
C31 C30 C29 112.4(2) . . ?
C31 C30 H30A 109.1 . . ?
C31 C30 H30B 109.1 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 108.1 . . ?
C32 C31 C30 110.7(2) . . ?
C32 C31 H31A 109.5 . . ?
C32 C31 H31B 109.5 . . ?
C31 C32 H32A 109.3 . . ?
C31 C32 H32B 109.3 . . ?
H32A C32 H32B 108.0 . . ?
C33 C32 C31 111.5(2) . . ?
C33 C32 H32A 109.3 . . ?
C33 C32 H32B 109.3 . . ?
C32 C33 H33A 109.3 . . ?
C32 C33 H33B 109.3 . . ?
C32 C33 C34 111.7(2) . . ?
H33A C33 H33B 107.9 . . ?
C34 C33 H33A 109.3 . . ?
C34 C33 H33B 109.3 . . ?
C29 C34 H34A 109.3 . . ?
C29 C34 H34B 109.3 . . ?
C33 C34 C29 111.8(2) . . ?
C33 C34 H34A 109.3 . . ?
C33 C34 H34B 109.3 . . ?
H34A C34 H34B 107.9 . . ?
C36 C35 C27 122.4(2) . . ?
C36 C35 C40 118.0(2) . . ?
C40 C35 C27 119.5(2) . . ?
C35 C36 H36 119.5 . . ?
C37 C36 C35 121.0(3) . . ?
C37 C36 H36 119.5 . . ?
C36 C37 H37 119.8 . . ?
C38 C37 C36 120.3(3) . . ?
C38 C37 H37 119.8 . . ?
C37 C38 H38 120.2 . . ?
C39 C38 C37 119.6(3) . . ?
C39 C38 H38 120.2 . . ?
C38 C39 H39 119.9 . . ?
C38 C39 C40 120.2(3) . . ?
C40 C39 H39 119.9 . . ?
C35 C40 H40 119.6 . . ?
C39 C40 C35 120.9(3) . . ?
C39 C40 H40 119.6 . . ?
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
N001 C5 1.315(3) . ?
N001 C7 1.382(3) . ?
N002 C1 1.383(3) . ?
N002 C5 1.396(3) . ?
N002 C9 1.508(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.343(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.417(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.361(4) . ?
C4 C5 1.442(3) . ?
C4 C6 1.495(4) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.343(4) . ?
C7 C15 1.493(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.504(4) . ?
C9 C10 1.543(3) . ?
C9 C14 1.542(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.536(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.525(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.522(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.527(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.397(4) . ?
C15 C20 1.389(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.392(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.374(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.388(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.385(4) . ?
C20 H20 0.9500 . ?
N003 C24 1.386(3) . ?
N003 C25 1.391(3) . ?
N003 C29 1.506(3) . ?
N004 C25 1.316(3) . ?
N004 C27 1.382(3) . ?
C21 C22 1.354(4) . ?
C21 C25 1.445(4) . ?
C21 C26 1.506(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.414(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.343(4) . ?
C24 H24 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C28 1.343(4) . ?
C27 C35 1.497(4) . ?
C28 H28 0.9500 . ?
C28 C29 1.503(4) . ?
C29 C30 1.540(4) . ?
C29 C34 1.552(4) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C30 C31 1.530(4) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.528(4) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C32 C33 1.514(4) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C33 C34 1.532(4) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.390(4) . ?
C35 C40 1.394(4) . ?
C36 H36 0.9500 . ?
C36 C37 1.385(4) . ?
C37 H37 0.9500 . ?
C37 C38 1.383(4) . ?
C38 H38 0.9500 . ?
C38 C39 1.376(4) . ?
C39 H39 0.9500 . ?
C39 C40 1.393(4) . ?
C40 H40 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
N001 C7 C8 C9 -6.5(4) . . . . ?
N001 C7 C15 C16 9.7(3) . . . . ?
N001 C7 C15 C20 -173.2(2) . . . . ?
N002 C1 C2 C3 -0.3(4) . . . . ?
N002 C9 C10 C11 -176.2(2) . . . . ?
N002 C9 C14 C13 179.2(2) . . . . ?
C1 N002 C5 N001 -179.7(2) . . . . ?
C1 N002 C5 C4 -2.0(3) . . . . ?
C1 N002 C9 C8 167.1(2) . . . . ?
C1 N002 C9 C10 46.7(3) . . . . ?
C1 N002 C9 C14 -72.9(3) . . . . ?
C1 C2 C3 C4 0.8(4) . . . . ?
C2 C3 C4 C5 -1.9(4) . . . . ?
C2 C3 C4 C6 177.3(3) . . . . ?
C3 C4 C5 N001 -179.7(3) . . . . ?
C3 C4 C5 N002 2.4(4) . . . . ?
C5 N001 C7 C8 -9.6(4) . . . . ?
C5 N001 C7 C15 169.0(2) . . . . ?
C5 N002 C1 C2 1.0(4) . . . . ?
C5 N002 C9 C8 -23.4(3) . . . . ?
C5 N002 C9 C10 -143.8(2) . . . . ?
C5 N002 C9 C14 96.6(3) . . . . ?
C6 C4 C5 N001 1.1(4) . . . . ?
C6 C4 C5 N002 -176.7(2) . . . . ?
C7 N001 C5 N002 7.1(4) . . . . ?
C7 N001 C5 C4 -170.6(2) . . . . ?
C7 C8 C9 N002 21.5(3) . . . . ?
C7 C8 C9 C10 142.8(3) . . . . ?
C7 C8 C9 C14 -96.7(3) . . . . ?
C7 C15 C16 C17 176.7(3) . . . . ?
C7 C15 C20 C19 -176.8(2) . . . . ?
C8 C7 C15 C16 -171.7(3) . . . . ?
C8 C7 C15 C20 5.4(4) . . . . ?
C8 C9 C10 C11 64.9(3) . . . . ?
C8 C9 C14 C13 -63.2(3) . . . . ?
C9 N002 C1 C2 170.5(3) . . . . ?
C9 N002 C5 N001 11.0(4) . . . . ?
C9 N002 C5 C4 -171.3(2) . . . . ?
C9 C10 C11 C12 55.2(3) . . . . ?
C10 C9 C14 C13 58.0(3) . . . . ?
C10 C11 C12 C13 -52.6(3) . . . . ?
C11 C12 C13 C14 53.3(3) . . . . ?
C12 C13 C14 C9 -56.9(3) . . . . ?
C14 C9 C10 C11 -57.0(3) . . . . ?
C15 C7 C8 C9 175.0(2) . . . . ?
C15 C16 C17 C18 -0.4(5) . . . . ?
C16 C15 C20 C19 0.4(4) . . . . ?
C16 C17 C18 C19 1.5(5) . . . . ?
C17 C18 C19 C20 -1.7(4) . . . . ?
C18 C19 C20 C15 0.8(4) . . . . ?
C20 C15 C16 C17 -0.6(4) . . . . ?
N003 C29 C30 C31 -177.3(2) . . . . ?
N003 C29 C34 C33 174.4(2) . . . . ?
N004 C27 C28 C29 6.4(4) . . . . ?
N004 C27 C35 C36 174.6(3) . . . . ?
N004 C27 C35 C40 -8.0(3) . . . . ?
C21 C22 C23 C24 -0.3(5) . . . . ?
C22 C21 C25 N003 -1.6(4) . . . . ?
C22 C21 C25 N004 -179.4(3) . . . . ?
C22 C23 C24 N003 0.0(5) . . . . ?
C24 N003 C25 N004 178.9(3) . . . . ?
C24 N003 C25 C21 1.3(4) . . . . ?
C24 N003 C29 C28 -165.5(2) . . . . ?
C24 N003 C29 C30 73.6(3) . . . . ?
C24 N003 C29 C34 -45.2(3) . . . . ?
C25 N003 C24 C23 -0.6(4) . . . . ?
C25 N003 C29 C28 25.2(3) . . . . ?
C25 N003 C29 C30 -95.6(3) . . . . ?
C25 N003 C29 C34 145.5(2) . . . . ?
C25 N004 C27 C28 10.8(4) . . . . ?
C25 N004 C27 C35 -168.7(2) . . . . ?
C25 C21 C22 C23 1.1(4) . . . . ?
C26 C21 C22 C23 -177.3(3) . . . . ?
C26 C21 C25 N003 176.9(2) . . . . ?
C26 C21 C25 N004 -0.8(4) . . . . ?
C27 N004 C25 N003 -7.8(4) . . . . ?
C27 N004 C25 C21 169.8(2) . . . . ?
C27 C28 C29 N003 -22.9(3) . . . . ?
C27 C28 C29 C30 95.7(3) . . . . ?
C27 C28 C29 C34 -144.1(3) . . . . ?
C27 C35 C36 C37 176.4(3) . . . . ?
C27 C35 C40 C39 -176.2(3) . . . . ?
C28 C27 C35 C36 -4.9(4) . . . . ?
C28 C27 C35 C40 172.5(3) . . . . ?
C28 C29 C30 C31 64.5(3) . . . . ?
C28 C29 C34 C33 -66.6(3) . . . . ?
C29 N003 C24 C23 -169.9(3) . . . . ?
C29 N003 C25 N004 -11.9(4) . . . . ?
C29 N003 C25 C21 170.6(2) . . . . ?
C29 C30 C31 C32 57.0(3) . . . . ?
C30 C29 C34 C33 55.7(3) . . . . ?
C30 C31 C32 C33 -54.9(3) . . . . ?
C31 C32 C33 C34 54.9(3) . . . . ?
C32 C33 C34 C29 -56.0(3) . . . . ?
C34 C29 C30 C31 -56.6(3) . . . . ?
C35 C27 C28 C29 -174.2(2) . . . . ?
C35 C36 C37 C38 -0.6(5) . . . . ?
C36 C35 C40 C39 1.3(4) . . . . ?
C36 C37 C38 C39 2.0(5) . . . . ?
C37 C38 C39 C40 -1.8(5) . . . . ?
C38 C39 C40 C35 0.1(5) . . . . ?
C40 C35 C36 C37 -1.1(4) . . . . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.652(2) 6215 13810 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.348(2) 0 13810 nmt 1.0001 -0.0005 -0.0003 -0.0009 -0.9998 -0.0001 -0.6808
0.0020 -0.9998
