#------------------------------------------------------------------------------
#$Date: 2021-06-05 04:22:50 +0300 (Sat, 05 Jun 2021) $
#$Revision: 265817 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/31/1563161.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_1563161
loop_
_publ_author_name
'Tan, Jin-Fay'
'Bormann, Carl Thomas'
'Severin, Kay'
'Cramer, Nicolai'
_publ_section_title
;
 Alkynyl Triazenes Enable Divergent Syntheses of 2-Pyrones
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC02583J
_journal_year                    2021
_chemical_formula_moiety         'C20 H25 N3 O2'
_chemical_formula_sum            'C20 H25 N3 O2'
_chemical_formula_weight         339.43
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-12-10
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-04-06 deposited with the CCDC.	2021-06-04 downloaded from the CCDC.
;
_cell_angle_alpha                109.270(6)
_cell_angle_beta                 97.031(5)
_cell_angle_gamma                111.857(6)
_cell_formula_units_Z            4
_cell_length_a                   10.4488(6)
_cell_length_b                   13.1778(8)
_cell_length_c                   15.6415(10)
_cell_measurement_reflns_used    3996
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      71.6530
_cell_measurement_theta_min      3.0840
_cell_volume                     1811.5(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2665
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00 -15.00   1.00    1.50    --  -43.01  95.00-174.00   45
  2  ω     23.00  69.00   1.00    1.50    --   43.01 -95.00  75.00   46
  3  ω     60.00 106.00   1.00    6.00    --  103.80 -95.00  75.00   46
  4  ω    104.00 171.00   1.00    6.00    --  103.80  95.00-174.00   67
  5  ω   -105.00 -17.00   1.00    1.50    --  -43.01 -57.00-120.00   88
  6  ω    -79.00  -8.00   1.00    1.50    --  -43.01 125.00  60.00   71
  7  ω   -112.00 -20.00   1.00    1.50    --  -43.01 -57.00   0.00   92
  8  ω     19.00 100.00   1.00    1.50    --   43.01  37.00   0.00   81
  9  ω     76.00 168.00   1.00    6.00    --  103.80  30.00-180.00   92
 10  ω     30.00  57.00   1.00    6.00    --  103.80-111.00-120.00   27
 11  ω    103.00 176.00   1.00    6.00    --  103.80  77.00-120.00   73
 12  ω     29.00 108.00   1.00    6.00    --  103.80-111.00 -30.00   79
 13  ω     37.00 106.00   1.00    6.00    --  103.80-111.00  60.00   69
 14  ω     76.00 103.00   1.00    6.00    --  103.80  30.00 120.00   27
 15  ω    116.00 176.00   1.00    6.00    --  103.80  30.00 120.00   60
 16  ω    141.00 166.00   1.00    6.00    --  103.80 111.00-120.00   25
 17  ω     42.00  95.00   1.00    6.00    --  103.80-111.00-180.00   53
 18  ω     67.00 108.00   1.00    6.00    --  103.80-111.00-120.00   41
 19  ω     73.00 124.00   1.00    6.00    --  103.80 178.00  90.00   51
 20  ω     55.00 130.00   1.00    6.00    --  103.80 -45.00 120.00   75
 21  ω    108.00 168.00   1.00    6.00    --  103.80 111.00  30.00   60
 22  ω    129.00 178.00   1.00    6.00    --  103.80  77.00  90.00   49
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0577797000
_diffrn_orient_matrix_UB_12      0.1331357000
_diffrn_orient_matrix_UB_13      0.0661456000
_diffrn_orient_matrix_UB_21      -0.0813410000
_diffrn_orient_matrix_UB_22      0.0198889000
_diffrn_orient_matrix_UB_23      -0.0772177000
_diffrn_orient_matrix_UB_31      -0.1320102000
_diffrn_orient_matrix_UB_32      -0.0301497000
_diffrn_orient_matrix_UB_33      0.0383940000
_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  0.0446
_diffrn_reflns_av_unetI/netI     0.0548
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15128
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.679
_diffrn_reflns_theta_min         3.118
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.664
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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_density_diffrn    1.245
_exptl_crystal_description       irregular
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.236
_exptl_crystal_size_mid          0.174
_exptl_crystal_size_min          0.122
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     648
_refine_ls_number_reflns         7000
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0859
_refine_ls_R_factor_gt           0.0654
_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)+(0.0917P)²+0.5831P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1676
_refine_ls_wR_factor_ref         0.1839
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5303
_reflns_number_total             7000
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc02583j2.cif
_cod_data_source_block           jft-r352
_cod_database_code               1563161
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C20 H25 N3 O2'
_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   0.925
_shelx_estimated_absorpt_t_min   0.862
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
;
_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 2.437
_oxdiff_exptl_absorpt_empirical_full_min 0.654
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 1.1812(2) 0.84471(18) 0.28406(15) 0.0378(5) Uani 1 1 d . . . . .
O2 O 1.05477(17) 0.72483(15) 0.34475(12) 0.0282(4) Uani 1 1 d . . . . .
N1 N 0.9192(2) 0.60890(19) 0.41444(15) 0.0282(4) Uani 1 1 d . . . . .
N2 N 0.8031(2) 0.60804(19) 0.44843(15) 0.0271(4) Uani 1 1 d . . . . .
N3 N 0.7418(2) 0.52985(18) 0.49060(15) 0.0265(4) Uani 1 1 d . . . . .
C1 C 1.0805(3) 0.8186(2) 0.31622(18) 0.0295(5) Uani 1 1 d . . . . .
C2 C 0.9829(3) 0.8741(2) 0.32612(18) 0.0296(5) Uani 1 1 d . . . . .
H2 H 1.006(3) 0.938(3) 0.304(2) 0.022(6) Uiso 1 1 d . . . . .
C3 C 0.8698(2) 0.8408(2) 0.36182(17) 0.0258(5) Uani 1 1 d . . . . .
C4 C 0.8490(2) 0.7467(2) 0.39366(17) 0.0254(5) Uani 1 1 d . . . . .
C5 C 0.9439(2) 0.6932(2) 0.38303(17) 0.0251(5) Uani 1 1 d . . . . .
C6 C 0.7713(3) 0.8986(2) 0.36751(17) 0.0271(5) Uani 1 1 d . . . . .
C7 C 0.8255(3) 1.0229(2) 0.4151(2) 0.0338(5) Uani 1 1 d . . . . .
H7 H 0.921(4) 1.070(3) 0.442(2) 0.041 Uiso 1 1 d . U . . .
C8 C 0.7324(4) 1.0754(3) 0.4253(2) 0.0437(7) Uani 1 1 d . . . . .
H8 H 0.774(4) 1.164(4) 0.458(3) 0.060(11) Uiso 1 1 d . . . . .
C9 C 0.5859(4) 1.0060(3) 0.3875(2) 0.0458(7) Uani 1 1 d . . . . .
H9 H 0.521(4) 1.042(4) 0.395(3) 0.061(11) Uiso 1 1 d . . . . .
C10 C 0.5306(3) 0.8830(3) 0.3382(2) 0.0394(6) Uani 1 1 d . . . . .
H10 H 0.435(4) 0.840(3) 0.312(2) 0.035(8) Uiso 1 1 d . . . . .
C11 C 0.6234(3) 0.8293(2) 0.32819(19) 0.0314(5) Uani 1 1 d . . . . .
H11 H 0.584(3) 0.741(3) 0.292(2) 0.032(7) Uiso 1 1 d . . . . .
C12 C 0.7595(2) 0.6895(2) 0.43951(17) 0.0261(5) Uani 1 1 d . . . . .
C13 C 0.6431(3) 0.7085(2) 0.4794(2) 0.0310(5) Uani 1 1 d . . . . .
H13A H 0.611(3) 0.648(3) 0.502(2) 0.032(7) Uiso 1 1 d . . . . .
H13B H 0.575(3) 0.703(3) 0.434(2) 0.024(7) Uiso 1 1 d . . . . .
C14 C 0.6980(3) 0.8302(3) 0.5617(2) 0.0408(7) Uani 1 1 d . . . . .
H14A H 0.742(4) 0.892(3) 0.545(2) 0.041(9) Uiso 1 1 d . . . . .
H14B H 0.620(4) 0.847(4) 0.586(3) 0.061(11) Uiso 1 1 d . . . . .
H14C H 0.778(5) 0.837(4) 0.615(3) 0.067(12) Uiso 1 1 d . . . . .
C15 C 0.8534(3) 0.5459(2) 0.56906(19) 0.0318(5) Uani 1 1 d . . . . .
H15 H 0.933(3) 0.530(3) 0.543(2) 0.030(7) Uiso 1 1 d . . . . .
C16 C 0.9183(3) 0.6737(3) 0.6422(2) 0.0408(6) Uani 1 1 d . . . . .
H16A H 0.986(4) 0.683(3) 0.689(3) 0.037(8) Uiso 1 1 d . . . . .
H16B H 0.843(3) 0.693(3) 0.668(2) 0.035(8) Uiso 1 1 d . . . . .
H16C H 0.967(4) 0.734(3) 0.617(3) 0.045(9) Uiso 1 1 d . . . . .
C17 C 0.7887(3) 0.4593(3) 0.6132(2) 0.0395(6) Uani 1 1 d . . . . .
H17A H 0.755(4) 0.376(4) 0.577(3) 0.050(10) Uiso 1 1 d . . . . .
H17B H 0.865(4) 0.480(3) 0.667(3) 0.041(8) Uiso 1 1 d . . . . .
H17C H 0.706(4) 0.475(4) 0.633(3) 0.061(11) Uiso 1 1 d . . . . .
C18 C 0.6530(3) 0.4054(2) 0.41887(18) 0.0296(5) Uani 1 1 d . . . . .
H18 H 0.605(3) 0.359(3) 0.455(2) 0.032(8) Uiso 1 1 d . . . . .
C19 C 0.5361(3) 0.4019(3) 0.3488(2) 0.0393(6) Uani 1 1 d . . . . .
H19A H 0.474(4) 0.320(4) 0.307(3) 0.047(9) Uiso 1 1 d . . . . .
H19B H 0.480(4) 0.436(4) 0.376(3) 0.054(10) Uiso 1 1 d . . . . .
H19C H 0.573(4) 0.444(4) 0.310(3) 0.053(10) Uiso 1 1 d . . . . .
C20 C 0.7354(3) 0.3416(3) 0.3691(2) 0.0398(7) Uani 1 1 d . . . . .
H20A H 0.777(4) 0.377(3) 0.326(3) 0.048(9) Uiso 1 1 d . . . . .
H20B H 0.818(4) 0.342(3) 0.415(3) 0.050(10) Uiso 1 1 d . . . . .
H20C H 0.662(5) 0.252(4) 0.329(3) 0.070(12) Uiso 1 1 d . . . . .
O3 O 1.35269(18) 0.56739(17) 0.19687(15) 0.0371(4) Uani 1 1 d . . . . .
O4 O 1.17935(17) 0.38430(15) 0.14724(13) 0.0282(4) Uani 1 1 d . . . . .
N4 N 0.9891(2) 0.19446(18) 0.08330(15) 0.0269(4) Uani 1 1 d . . . . .
N5 N 0.8432(2) 0.15413(18) 0.04891(15) 0.0254(4) Uani 1 1 d . . . . .
N6 N 0.7483(2) 0.03239(17) 0.01277(14) 0.0252(4) Uani 1 1 d . . . . .
C21 C 1.2250(3) 0.5059(2) 0.16815(18) 0.0283(5) Uani 1 1 d . . . . .
C22 C 1.1156(3) 0.5480(2) 0.15835(18) 0.0283(5) Uani 1 1 d . . . . .
H22 H 1.150(3) 0.637(3) 0.179(2) 0.034 Uiso 1 1 d . U . . .
C23 C 0.9723(3) 0.4752(2) 0.12615(17) 0.0258(5) Uani 1 1 d . . . . .
C24 C 0.9291(2) 0.3489(2) 0.09801(17) 0.0257(5) Uani 1 1 d . . . . .
C25 C 1.0364(2) 0.3105(2) 0.11089(17) 0.0255(5) Uani 1 1 d . . . . .
C26 C 0.8662(3) 0.5241(2) 0.12129(17) 0.0269(5) Uani 1 1 d . . . . .
C27 C 0.8823(3) 0.6069(2) 0.08107(19) 0.0325(5) Uani 1 1 d . . . . .
H27 H 0.963(3) 0.632(3) 0.057(2) 0.032(7) Uiso 1 1 d . . . . .
C28 C 0.7804(4) 0.6496(3) 0.0734(2) 0.0413(7) Uani 1 1 d . . . . .
H28 H 0.789(4) 0.702(4) 0.039(3) 0.056(10) Uiso 1 1 d . . . . .
C29 C 0.6620(3) 0.6117(3) 0.1071(2) 0.0425(7) Uani 1 1 d . . . . .
H29 H 0.582(4) 0.640(4) 0.096(3) 0.058(11) Uiso 1 1 d . . . . .
C30 C 0.6471(3) 0.5326(3) 0.1496(2) 0.0387(6) Uani 1 1 d . . . . .
H30 H 0.566(5) 0.507(4) 0.172(3) 0.068(12) Uiso 1 1 d . . . . .
C31 C 0.7483(3) 0.4890(2) 0.15656(19) 0.0316(5) Uani 1 1 d . . . . .
H31 H 0.739(3) 0.437(3) 0.184(2) 0.035(8) Uiso 1 1 d . . . . .
C32 C 0.8022(2) 0.2420(2) 0.05392(17) 0.0254(5) Uani 1 1 d . . . . .
C33 C 0.6512(3) 0.2133(2) 0.00947(19) 0.0290(5) Uani 1 1 d . . . . .
H33A H 0.593(3) 0.125(3) -0.010(2) 0.025(7) Uiso 1 1 d . . . . .
H33B H 0.613(3) 0.254(3) 0.057(2) 0.037(8) Uiso 1 1 d . . . . .
C34 C 0.6386(3) 0.2492(3) -0.0738(2) 0.0363(6) Uani 1 1 d . . . . .
H34A H 0.538(4) 0.219(3) -0.106(2) 0.040(8) Uiso 1 1 d . . . . .
H34B H 0.689(4) 0.333(3) -0.056(2) 0.042(9) Uiso 1 1 d . . . . .
H34C H 0.687(4) 0.213(4) -0.117(3) 0.057(11) Uiso 1 1 d . . . . .
C35 C 0.7307(3) -0.0104(2) 0.08985(18) 0.0278(5) Uani 1 1 d . . . . .
H35 H 0.650(3) -0.092(3) 0.058(2) 0.035(8) Uiso 1 1 d . . . . .
C36 C 0.6809(3) 0.0655(3) 0.1619(2) 0.0361(6) Uani 1 1 d . . . . .
H36A H 0.659(3) 0.028(3) 0.204(2) 0.032(7) Uiso 1 1 d . . . . .
H36B H 0.599(4) 0.071(3) 0.134(3) 0.045(9) Uiso 1 1 d . . . . .
H36C H 0.763(4) 0.146(3) 0.198(2) 0.040(8) Uiso 1 1 d . . . . .
C37 C 0.8592(3) -0.0199(3) 0.1380(2) 0.0362(6) Uani 1 1 d . . . . .
H37A H 0.936(4) 0.056(3) 0.183(3) 0.046(9) Uiso 1 1 d . . . . .
H37B H 0.889(3) -0.071(3) 0.084(2) 0.038(8) Uiso 1 1 d . . . . .
H37C H 0.819(4) -0.065(4) 0.182(3) 0.055(10) Uiso 1 1 d . . . . .
C38 C 0.7892(3) -0.0375(2) -0.06611(18) 0.0296(5) Uani 1 1 d . . . . .
H38 H 0.887(3) -0.023(3) -0.040(2) 0.023(7) Uiso 1 1 d . . . . .
C39 C 0.7854(3) 0.0091(3) -0.1429(2) 0.0393(6) Uani 1 1 d . . . . .
H39A H 0.681(4) 0.002(3) -0.168(3) 0.047 Uiso 1 1 d . U . . .
H39B H 0.805(4) -0.038(3) -0.196(3) 0.046(9) Uiso 1 1 d . . . . .
H39C H 0.859(4) 0.096(4) -0.117(3) 0.048(9) Uiso 1 1 d . . . . .
C40 C 0.6856(3) -0.1695(3) -0.1055(2) 0.0380(6) Uani 1 1 d . . . . .
H40A H 0.592(4) -0.179(3) -0.126(2) 0.039(8) Uiso 1 1 d . . . . .
H40B H 0.687(4) -0.205(3) -0.059(3) 0.047(9) Uiso 1 1 d . . . . .
H40C H 0.717(4) -0.210(3) -0.158(3) 0.050(10) Uiso 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 -1 0.0903
-1 0 1 0.1133
5 3 -3 0.1021
-3 3 5 0.1060
3 -3 -5 0.0827
2 -5 0 0.0752
-2 5 0 0.1006
-5 5 3 0.0951
5 -5 -3 0.0730
-3 -5 5 0.1224
0 -5 2 0.0990
-2 5 -2 0.0892
-1 1 -1 0.0518
0 3 -5 0.0891
-5 3 -5 0.0536
0 -3 5 0.0883
2 1 2 0.0689
0 3 5 0.0746
2 0 -5 0.0894
0 0 -1 0.0810
-5 0 -3 0.0705
0 -5 -3 0.0919
2 -5 -5 0.0807
3 -5 1 0.0679
3 -5 4 0.0518
5 -2 -1 0.0785
-2 -1 5 0.0990
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 O2 C1 118.61(19) . . ?
C5 N1 N2 101.81(19) . . ?
N1 N2 N3 120.87(19) . . ?
C12 N2 N1 114.34(19) . . ?
C12 N2 N3 124.76(18) . . ?
N2 N3 C15 110.09(19) . . ?
N2 N3 C18 111.37(19) . . ?
C15 N3 C18 116.4(2) . . ?
O1 C1 O2 116.3(2) . . ?
O1 C1 C2 126.1(2) . . ?
O2 C1 C2 117.6(2) . . ?
C3 C2 C1 124.1(2) . . ?
C2 C3 C4 117.0(2) . . ?
C2 C3 C6 121.6(2) . . ?
C4 C3 C6 121.4(2) . . ?
C5 C4 C3 118.2(2) . . ?
C12 C4 C3 138.1(2) . . ?
C12 C4 C5 103.6(2) . . ?
O2 C5 C4 124.4(2) . . ?
N1 C5 O2 120.8(2) . . ?
N1 C5 C4 114.8(2) . . ?
C7 C6 C3 120.3(2) . . ?
C11 C6 C3 120.4(2) . . ?
C11 C6 C7 119.3(2) . . ?
C8 C7 C6 120.0(3) . . ?
C9 C8 C7 120.4(3) . . ?
C8 C9 C10 120.3(3) . . ?
C9 C10 C11 119.7(3) . . ?
C10 C11 C6 120.3(3) . . ?
N2 C12 C4 105.4(2) . . ?
N2 C12 C13 121.9(2) . . ?
C4 C12 C13 132.6(2) . . ?
C12 C13 C14 112.9(2) . . ?
N3 C15 C16 109.2(2) . . ?
N3 C15 C17 110.3(2) . . ?
C16 C15 C17 110.3(2) . . ?
N3 C18 C19 110.2(2) . . ?
N3 C18 C20 115.8(2) . . ?
C19 C18 C20 111.5(2) . . ?
C25 O4 C21 118.13(19) . . ?
C25 N4 N5 101.89(19) . . ?
N4 N5 N6 121.46(19) . . ?
C32 N5 N4 114.37(19) . . ?
C32 N5 N6 124.17(19) . . ?
N5 N6 C35 111.15(19) . . ?
N5 N6 C38 110.25(17) . . ?
C38 N6 C35 115.94(19) . . ?
O3 C21 O4 116.1(2) . . ?
O3 C21 C22 125.9(2) . . ?
O4 C21 C22 117.9(2) . . ?
C23 C22 C21 123.9(2) . . ?
C22 C23 C24 116.8(2) . . ?
C22 C23 C26 121.3(2) . . ?
C24 C23 C26 122.0(2) . . ?
C25 C24 C23 118.4(2) . . ?
C32 C24 C23 137.8(2) . . ?
C32 C24 C25 103.7(2) . . ?
O4 C25 C24 124.6(2) . . ?
N4 C25 O4 120.4(2) . . ?
N4 C25 C24 114.9(2) . . ?
C27 C26 C23 120.5(2) . . ?
C31 C26 C23 121.0(2) . . ?
C31 C26 C27 118.5(2) . . ?
C28 C27 C26 120.6(2) . . ?
C27 C28 C29 120.1(3) . . ?
C30 C29 C28 119.8(3) . . ?
C29 C30 C31 120.1(3) . . ?
C30 C31 C26 120.8(3) . . ?
N5 C32 C24 105.0(2) . . ?
N5 C32 C33 121.4(2) . . ?
C24 C32 C33 133.3(2) . . ?
C32 C33 C34 112.5(2) . . ?
N6 C35 C36 109.6(2) . . ?
N6 C35 C37 116.44(19) . . ?
C36 C35 C37 111.1(2) . . ?
N6 C38 C39 108.7(2) . . ?
N6 C38 C40 110.1(2) . . ?
C40 C38 C39 110.0(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 1.206(3) . ?
O2 C1 1.394(3) . ?
O2 C5 1.360(3) . ?
N1 N2 1.381(3) . ?
N1 C5 1.311(3) . ?
N2 N3 1.403(3) . ?
N2 C12 1.352(3) . ?
N3 C15 1.485(3) . ?
N3 C18 1.485(3) . ?
C1 C2 1.455(4) . ?
C2 C3 1.356(3) . ?
C3 C4 1.438(3) . ?
C3 C6 1.486(3) . ?
C4 C5 1.412(3) . ?
C4 C12 1.397(3) . ?
C6 C7 1.400(4) . ?
C6 C11 1.395(4) . ?
C7 C8 1.385(4) . ?
C8 C9 1.381(5) . ?
C9 C10 1.387(5) . ?
C10 C11 1.394(4) . ?
C12 C13 1.496(3) . ?
C13 C14 1.527(4) . ?
C15 C16 1.514(4) . ?
C15 C17 1.516(4) . ?
C18 C19 1.514(4) . ?
C18 C20 1.525(4) . ?
O3 C21 1.203(3) . ?
O4 C21 1.396(3) . ?
O4 C25 1.359(3) . ?
N4 N5 1.379(3) . ?
N4 C25 1.311(3) . ?
N5 N6 1.399(3) . ?
N5 C32 1.359(3) . ?
N6 C35 1.493(3) . ?
N6 C38 1.491(3) . ?
C21 C22 1.457(4) . ?
C22 C23 1.358(3) . ?
C23 C24 1.441(3) . ?
C23 C26 1.482(3) . ?
C24 C25 1.409(3) . ?
C24 C32 1.401(3) . ?
C26 C27 1.398(4) . ?
C26 C31 1.395(3) . ?
C27 C28 1.387(4) . ?
C28 C29 1.390(5) . ?
C29 C30 1.385(5) . ?
C30 C31 1.387(4) . ?
C32 C33 1.494(3) . ?
C33 C34 1.531(4) . ?
C35 C36 1.525(4) . ?
C35 C37 1.526(4) . ?
C38 C39 1.521(4) . ?
C38 C40 1.518(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 179.2(3) . . . . ?
O2 C1 C2 C3 0.5(4) . . . . ?
N1 N2 N3 C15 54.8(3) . . . . ?
N1 N2 N3 C18 -75.8(3) . . . . ?
N1 N2 C12 C4 2.0(3) . . . . ?
N1 N2 C12 C13 -175.0(2) . . . . ?
N2 N1 C5 O2 178.5(2) . . . . ?
N2 N1 C5 C4 -0.7(3) . . . . ?
N2 N3 C15 C16 60.2(2) . . . . ?
N2 N3 C15 C17 -178.5(2) . . . . ?
N2 N3 C18 C19 -57.8(2) . . . . ?
N2 N3 C18 C20 69.8(3) . . . . ?
N2 C12 C13 C14 111.8(3) . . . . ?
N3 N2 C12 C4 -179.8(2) . . . . ?
N3 N2 C12 C13 3.2(4) . . . . ?
C1 O2 C5 N1 -177.2(2) . . . . ?
C1 O2 C5 C4 2.0(4) . . . . ?
C1 C2 C3 C4 1.6(4) . . . . ?
C1 C2 C3 C6 -178.1(2) . . . . ?
C2 C3 C4 C5 -2.0(3) . . . . ?
C2 C3 C4 C12 174.4(3) . . . . ?
C2 C3 C6 C7 -55.7(3) . . . . ?
C2 C3 C6 C11 126.4(3) . . . . ?
C3 C4 C5 O2 0.2(4) . . . . ?
C3 C4 C5 N1 179.4(2) . . . . ?
C3 C4 C12 N2 -178.9(3) . . . . ?
C3 C4 C12 C13 -2.4(5) . . . . ?
C3 C6 C7 C8 -175.9(2) . . . . ?
C3 C6 C11 C10 176.4(2) . . . . ?
C4 C3 C6 C7 124.5(3) . . . . ?
C4 C3 C6 C11 -53.4(3) . . . . ?
C4 C12 C13 C14 -64.3(4) . . . . ?
C5 O2 C1 O1 178.9(2) . . . . ?
C5 O2 C1 C2 -2.2(3) . . . . ?
C5 N1 N2 N3 -179.1(2) . . . . ?
C5 N1 N2 C12 -0.9(3) . . . . ?
C5 C4 C12 N2 -2.2(3) . . . . ?
C5 C4 C12 C13 174.3(3) . . . . ?
C6 C3 C4 C5 177.8(2) . . . . ?
C6 C3 C4 C12 -5.8(5) . . . . ?
C6 C7 C8 C9 -1.0(4) . . . . ?
C7 C6 C11 C10 -1.5(4) . . . . ?
C7 C8 C9 C10 -0.5(5) . . . . ?
C8 C9 C10 C11 1.1(5) . . . . ?
C9 C10 C11 C6 0.0(4) . . . . ?
C11 C6 C7 C8 2.1(4) . . . . ?
C12 N2 N3 C15 -123.2(2) . . . . ?
C12 N2 N3 C18 106.2(3) . . . . ?
C12 C4 C5 O2 -177.3(2) . . . . ?
C12 C4 C5 N1 1.9(3) . . . . ?
C15 N3 C18 C19 174.9(2) . . . . ?
C15 N3 C18 C20 -57.5(3) . . . . ?
C18 N3 C15 C16 -171.90(19) . . . . ?
C18 N3 C15 C17 -50.5(3) . . . . ?
O3 C21 C22 C23 -179.5(3) . . . . ?
O4 C21 C22 C23 -3.0(4) . . . . ?
N4 N5 N6 C35 72.7(2) . . . . ?
N4 N5 N6 C38 -57.3(3) . . . . ?
N4 N5 C32 C24 -2.3(3) . . . . ?
N4 N5 C32 C33 172.5(2) . . . . ?
N5 N4 C25 O4 -177.9(2) . . . . ?
N5 N4 C25 C24 1.1(3) . . . . ?
N5 N6 C35 C36 56.3(3) . . . . ?
N5 N6 C35 C37 -70.9(3) . . . . ?
N5 N6 C38 C39 -59.1(3) . . . . ?
N5 N6 C38 C40 -179.7(2) . . . . ?
N5 C32 C33 C34 -112.8(3) . . . . ?
N6 N5 C32 C24 177.4(2) . . . . ?
N6 N5 C32 C33 -7.7(3) . . . . ?
C21 O4 C25 N4 174.7(2) . . . . ?
C21 O4 C25 C24 -4.1(3) . . . . ?
C21 C22 C23 C24 -1.8(4) . . . . ?
C21 C22 C23 C26 177.6(2) . . . . ?
C22 C23 C24 C25 3.7(3) . . . . ?
C22 C23 C24 C32 -172.4(3) . . . . ?
C22 C23 C26 C27 47.9(3) . . . . ?
C22 C23 C26 C31 -132.1(3) . . . . ?
C23 C24 C25 O4 -0.8(3) . . . . ?
C23 C24 C25 N4 -179.7(2) . . . . ?
C23 C24 C32 N5 179.1(3) . . . . ?
C23 C24 C32 C33 5.2(5) . . . . ?
C23 C26 C27 C28 177.7(2) . . . . ?
C23 C26 C31 C30 -178.3(2) . . . . ?
C24 C23 C26 C27 -132.7(3) . . . . ?
C24 C23 C26 C31 47.4(3) . . . . ?
C24 C32 C33 C34 60.4(4) . . . . ?
C25 O4 C21 O3 -177.3(2) . . . . ?
C25 O4 C21 C22 5.8(3) . . . . ?
C25 N4 N5 N6 -178.9(2) . . . . ?
C25 N4 N5 C32 0.8(3) . . . . ?
C25 C24 C32 N5 2.6(2) . . . . ?
C25 C24 C32 C33 -171.3(2) . . . . ?
C26 C23 C24 C25 -175.7(2) . . . . ?
C26 C23 C24 C32 8.2(4) . . . . ?
C26 C27 C28 C29 1.0(4) . . . . ?
C27 C26 C31 C30 1.7(4) . . . . ?
C27 C28 C29 C30 0.9(5) . . . . ?
C28 C29 C30 C31 -1.6(5) . . . . ?
C29 C30 C31 C26 0.2(4) . . . . ?
C31 C26 C27 C28 -2.3(4) . . . . ?
C32 N5 N6 C35 -107.0(2) . . . . ?
C32 N5 N6 C38 123.0(2) . . . . ?
C32 C24 C25 O4 176.5(2) . . . . ?
C32 C24 C25 N4 -2.4(3) . . . . ?
C35 N6 C38 C39 173.5(2) . . . . ?
C35 N6 C38 C40 52.9(3) . . . . ?
C38 N6 C35 C36 -176.8(2) . . . . ?
C38 N6 C35 C37 56.0(3) . . . . ?
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
1.0004 -0.0001 -0.9995 -0.0083 -0.0042 -0.1704
-1.0004 0.0001 0.9995 0.0083 0.0042 0.1704
4.9999 3.0035 -2.9999 0.4903 -0.1153 -0.8658
-3.0035 3.0041 4.9958 0.5569 -0.0817 0.4977
3.0035 -3.0041 -4.9958 -0.5569 0.0817 -0.4977
2.0041 -5.0064 0.0034 -0.5505 -0.2628 -0.1135
-2.0041 5.0064 -0.0034 0.5505 0.2628 0.1135
-5.0053 5.0067 2.9950 0.5755 0.2755 0.6248
5.0053 -5.0067 -2.9950 -0.5755 -0.2755 -0.6248
-2.9980 -5.0060 5.0007 -0.5089 -0.2418 0.7387
0.0032 -5.0063 2.0023 -0.5339 -0.2544 0.2274
-2.0039 5.0064 -2.0026 0.4183 0.4172 0.0367
-1.0009 1.0013 -1.0004 0.0093 0.1786 0.0635
-0.0016 3.0037 -4.9999 0.0691 0.4460 -0.2823
-5.0033 3.0039 -5.0007 -0.2199 0.8529 0.3779
0.0016 -3.0037 4.9999 -0.0691 -0.4460 0.2823
1.9998 1.0012 1.9989 0.3811 -0.2971 -0.2174
-0.0025 3.0039 4.9962 0.7303 -0.3259 0.1016
2.0011 -0.0002 -4.9978 -0.2150 0.2231 -0.4560
0.0001 -0.0000 -0.9996 -0.0661 0.0772 -0.0384
-5.0015 0.0002 -2.9997 -0.4874 0.6385 0.5451
0.0036 -5.0064 -2.9958 -0.8645 0.1315 0.0354
2.0045 -5.0066 -4.9947 -0.8811 0.1231 -0.3054
3.0043 -5.0065 1.0032 -0.4266 -0.4214 -0.2071
3.0041 -5.0064 4.0020 -0.2282 -0.6530 -0.0920
5.0031 -2.0028 -0.9976 -0.0436 -0.3698 -0.6384
-2.0004 -1.0010 4.9984 0.0818 -0.2432 0.4862
