# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_anna_16002018_vlad211_3
_database_code_depnum_ccdc_archive 'CCDC 1875720'
_audit_update_record             
;
2018-10-28 deposited with the CCDC.	2019-02-12 downloaded from the CCDC.
;
_audit_creation_date             2018-10-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
alexaks05@rambler.ru
''
radioanimation@rambler.ru
''
mrubin@ku.edu
_chemical_name_common            ?
_chemical_name_systematic        2,5-diphenyl-1,3,4-oxadiazole
_chemical_formula_moiety         'C14 H10 N2 O'
_chemical_formula_sum            'C14 H10 N2 O'
_chemical_formula_weight         222.24
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C14H10N2O
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'I 1 a 1'
_space_group_name_Hall           'I -2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z'
'x+1/2, y+1/2, z+1/2'
'x+1, -y+1/2, z+1/2'

_cell_length_a                   12.71311(16)
_cell_length_b                   23.6491(3)
_cell_length_c                   22.6770(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.7321(12)
_cell_angle_gamma                90
_cell_volume                     6675.51(15)
_cell_formula_units_Z            24
_cell_measurement_reflns_used    66441
_cell_measurement_temperature    100.02(10)
_cell_measurement_theta_max      75.7070
_cell_measurement_theta_min      3.6740
_shelx_estimated_absorpt_T_max   0.847
_shelx_estimated_absorpt_T_min   0.720
_exptl_absorpt_coefficient_mu    0.689
_exptl_absorpt_correction_T_max  0.864
_exptl_absorpt_correction_T_min  0.776
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2784
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -15 0 0.2074
-4 13 0 0.1879
-8 -5 1 0.1692
1 -15 2 0.2311
3 -14 2 0.2410
0 -4 -14 0.2462
7 1 -9 0.1212
0 0 14 0.1688
-8 0 9 0.1146
-2 -14 7 0.2605
-4 -6 -10 0.1996
4 -3 11 0.1727
0 15 -2 0.2290
1 -12 -10 0.2425

_exptl_crystal_preparation       'Prepared by cyclisation of hydrazide in PPA'
_exptl_crystal_recrystallization_method 
'Crystallized by slow evaporation of saturated solution'
_exptl_crystal_size_max          0.511
_exptl_crystal_size_mid          0.458
_exptl_crystal_size_min          0.249
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
-1.0180 -15.2317 -0.0815 0.0311 -0.4120 0.9107
-4.1266 13.1527 -0.2685 -0.4597 -0.0840 -0.8841
-7.6764 -5.2698 0.8610 -0.6730 -0.7108 0.2045
0.5449 -15.0962 2.2443 0.0843 -0.1514 0.9849
2.5529 -14.1481 2.4356 0.2485 0.0480 0.9674
0.2688 -3.9243 -14.0206 0.5652 -0.8207 -0.0836
7.4651 1.2632 -8.7361 0.9723 0.1812 -0.1478
-0.1083 0.3021 14.4445 -0.5381 0.7807 0.3177
-7.5537 -0.4309 8.5280 -0.9791 -0.1824 0.0904
-1.5257 -13.5985 6.6954 -0.2737 -0.0527 0.9604
-3.7988 -5.7958 -10.2058 0.0791 -0.9958 0.0471
3.6494 -2.5404 11.3772 -0.0701 0.8706 0.4871
0.2844 15.1970 -2.0998 -0.0166 0.2312 -0.9728
0.5888 -11.6772 -9.5130 0.4898 -0.7131 0.5015

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0979
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            105927
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.258
_diffrn_reflns_theta_min         3.738
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.02(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -72.00  35.00   1.00    2.00    --  -41.72  27.00-168.00  107
  2  ω   -119.00 -11.00   1.00    2.00    --  -41.72 -27.00  29.00  108
  3  ω    -35.00  72.00   1.00    2.00    --   41.72 -27.00  29.00  107
  4  ω     11.00 119.00   1.00    2.00    --   41.72  27.00-168.00  108
  5  ω     35.00 143.00   1.00    8.00    --  112.00 -27.00  29.00  108
  6  ω     81.00 178.00   1.00    8.00    --  112.00  27.00-168.00   97
  7  ω     23.00  98.00   1.00    2.00    --   41.72-125.00 -90.00   75
  8  ω     23.00  98.00   1.00    2.00    --   41.72-125.00 150.00   75
  9  ω     23.00  98.00   1.00    2.00    --   41.72-125.00  90.00   75
 10  ω     36.00 116.00   1.00    8.00    --  112.00-111.00-150.00   80
 11  ω     39.00 138.00   1.00    8.00    --  112.00 -45.00  90.00   99
 12  ω     36.00 116.00   1.00    8.00    --  112.00-111.00 -90.00   80
 13  ω    100.00 178.00   1.00    8.00    --  112.00 111.00-180.00   78
 14  ω     83.00 178.00   1.00    8.00    --  112.00  61.00  90.00   95
 15  ω     57.00 151.00   1.00    8.00    --  112.00 178.00  30.00   94
 16  ω     40.00 141.00   1.00    8.00    --  112.00 -61.00-120.00  101
 17  ω     86.00 178.00   1.00    8.00    --  112.00  45.00-150.00   92
 18  ω     29.00  93.00   1.00    8.00    --  112.00 -94.00-120.00   64
 19  ω     30.00 109.00   1.00    8.00    --  112.00 -94.00  90.00   79
 20  ω     56.00 107.00   1.00    8.00    --  112.00-111.00  30.00   51
 21  ω      8.00  33.00   1.00    2.00    --  -41.60  38.00  90.00   25
 22  ω     64.00  94.00   1.00    8.00    --  112.00 -94.00  60.00   30
 23  ω     54.00  85.00   1.00    8.00    --  112.00 -30.00 -90.00   31
 24  ω   -118.00  -9.00   1.00    2.00    --  -41.60 -77.00  60.00  109
 25  ω   -118.00  -9.00   1.00    2.00    --  -41.60 -77.00 120.00  109
 26  ω   -114.00 -13.00   1.00    2.00    --  -41.60 -57.00 -60.00  101
 27  ω   -118.00  -9.00   1.00    2.00    --  -41.60 -77.00-150.00  109
 28  ω   -118.00  -9.00   1.00    2.00    --  -41.60 -77.00 -60.00  109
 29  ω      1.00  82.00   1.00    2.00    --   41.60 -99.00 -30.00   81
 30  ω     86.00 178.00   1.00    8.00    --  112.00  45.00  30.00   92
 31  ω     83.00 178.00   1.00    8.00    --  112.00  61.00 120.00   95
 32  ω     83.00 178.00   1.00    8.00    --  112.00  61.00 -30.00   95
 33  ω     84.00 178.00   1.00    8.00    --  112.00  30.00 -60.00   94
 34  ω     41.00  66.00   1.00    2.00    --   41.60  27.00-168.00   25
 35  ω    -39.00 -13.00   1.00    2.00    --  -41.60 -57.00   0.00   26
 36  ω     33.00  59.00   1.00    2.00    --   62.00  75.00  -5.70   26
 37  ω     38.00  63.00   1.00    2.00    --   70.00  76.00 -76.57   25
 38  ω     40.00  66.00   1.00    2.00    --   70.00  77.00 -58.93   26
 39  ω     41.00  69.00   1.00    2.00    --   74.00  77.00  -6.53   28
 40  ω     44.00  70.00   1.00    2.00    --   74.00  76.00  39.61   26
 41  ω     59.00  85.00   1.00    2.00    --   74.00  77.00-121.44   26
 42  ω     44.00  73.00   1.00    2.00    --   74.00  77.00 -52.70   29
 43  ω     45.00  73.00   1.00    8.00    --   78.00  77.00 -67.47   28
 44  ω     79.00 133.00   1.00    8.00    --  112.00  77.00 -60.00   54
 45  ω    130.00 178.00   1.00    8.00    --  112.00  77.00-150.00   48
 46  ω     83.00 135.00   1.00    8.00    --  112.00  61.00 -90.00   52
 47  ω     84.00 154.00   1.00    8.00    --  112.00  61.00-120.00   70
 48  ω     83.00 110.00   1.00    8.00    --  112.00  61.00   0.00   27
 49  ω     80.00 106.00   1.00    8.00    --  112.00  77.00-150.00   26
 50  ω     79.00 104.00   1.00    8.00    --  112.00  77.00-120.00   25
 51  ω     79.00 104.00   1.00    8.00    --  112.00  77.00 -30.00   25
 52  ω     79.00 105.00   1.00    8.00    --  112.00  77.00   0.00   26
 53  ω    122.00 148.00   1.00    8.00    --  112.00  77.00   0.00   26
 54  ω     87.00 113.00   1.00    8.00    --  112.00  45.00   0.00   26
 55  ω     88.00 115.00   1.00    8.00    --  112.00  45.00 -90.00   27
 56  ω     90.00 116.00   1.00    8.00    --  112.00  45.00 -60.00   26
 57  ω     79.00 105.00   1.00    8.00    --  112.00  77.00 -90.00   26
 58  ω    127.00 153.00   1.00    8.00    --  112.00  61.00   0.00   26
 59  ω     83.00 111.00   1.00    8.00    --  112.00  61.00 -60.00   28
 60  ω      4.00  32.00   1.00    2.00    --   41.60  90.00 125.62   28
 61  ω     20.00  46.00   1.00    2.00    --   54.00  81.00 -45.80   26
 62  ω     21.00  47.00   1.00    2.00    --   54.00  79.00-140.52   26
 63  ω     20.00  46.00   1.00    2.00    --   54.00  81.00 117.76   26
 64  ω     21.00  47.00   1.00    2.00    --   54.00  79.00  66.19   26
 65  ω     20.00  46.00   1.00    2.00    --   54.00  81.00 -97.61   26
 66  ω     21.00  47.00   1.00    2.00    --   54.00  79.00  21.40   26
 67  ω     20.00  46.00   1.00    2.00    --   54.00  81.00  88.96   26
 68  ω     20.00  46.00   1.00    2.00    --   54.00  81.00-179.44   26
 69  ω     37.00 146.00   1.00    2.00    --   70.00  77.00 119.10  109
 70  ω     37.00 146.00   1.00    2.00    --   70.00  77.00  14.68  109
 71  ω     41.00 150.00   1.00    2.00    --   74.00  77.00-121.44  109
 72  ω     41.00 150.00   1.00    2.00    --   74.00  77.00 170.03  109
 73  ω     41.00 150.00   1.00    2.00    --   74.00  77.00 155.71  109
 74  ω     42.00 133.00   1.00    2.00    --   74.00  76.00  64.53   91
 75  ω     42.00 150.00   1.00    2.00    --   74.00  76.00  91.83  108
 76  ω     42.00 150.00   1.00    2.00    --   74.00  76.00  39.61  108
 77  ω     41.00 150.00   1.00    2.00    --   74.00  77.00 -52.70  109
 78  ω     42.00 149.00   1.00    2.00    --   74.00  75.00  57.71  107
 79  ω     41.00 150.00   1.00    2.00    --   74.00  77.00-164.56  109
 80  ω     42.00 150.00   1.00    2.00    --   74.00  76.00-139.14  108
 81  ω     65.00  90.00   1.00    8.00    --  112.00 -27.00  28.00   25
 82  ω     41.00  66.00   1.00    2.00    --   41.60  27.00-168.00   25
 83  ω     41.00  66.00   1.00    2.00    --   41.60  27.00-168.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0889333000
_diffrn_orient_matrix_UB_12      -0.0077884000
_diffrn_orient_matrix_UB_13      -0.0364258000
_diffrn_orient_matrix_UB_21      0.0841736000
_diffrn_orient_matrix_UB_22      0.0211317000
_diffrn_orient_matrix_UB_23      0.0542361000
_diffrn_orient_matrix_UB_31      0.0179436000
_diffrn_orient_matrix_UB_32      -0.0611119000
_diffrn_orient_matrix_UB_33      0.0234091000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.970
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                13482
_reflns_number_total             13719
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.593
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 
;
 Flack x determined using 6098 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     813
_refine_ls_number_reflns         13719
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0768
_refine_ls_restrained_S_all      1.032
_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)+(0.1107P)²+11.7823P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1996
_refine_ls_wR_factor_ref         0.2005
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C25) = Uanis(C32)
Uanis(C26) = Uanis(C23)
Uanis(C23) = Uanis(C26)
Uanis(C7) = Uanis(C15)
Uanis(C16) = Uanis(C9)
Uanis(C10) = Uanis(C2)
Uanis(C1) = Uanis(C8)
3. Others
 Sof(N4)=Sof(N3)=Sof(C1)=Sof(C16)=1-FVAR(1)
 Sof(N1)=Sof(N2)=Sof(C8)=Sof(C9)=FVAR(1)
 Sof(C17)=Sof(N6)=Sof(N5)=Sof(C32)=1-FVAR(2)
 Sof(N7)=Sof(N8)=Sof(C24)=Sof(C25)=FVAR(2)
4.a Aromatic/amide H refined with riding coordinates:
 C53(H53), C51(H51), C52(H52), C50(H50), C49(H49), C74(H74), C73(H73),
 C72(H72), C71(H71), C70(H70), C56(H56), C57(H57), C58(H58), C59(H59), C60(H60),
  C82(H82), C81(H81), C80(H80), C79(H79), C78(H78), C42(H42), C43(H43),
 C44(H44), C45(H45), C46(H46), C38(H38), C39(H39), C37(H37), C36(H36), C35(H35),
  C85(H85), C86(H86), C87(H87), C88(H88), C89(H89), C67(H67), C66(H66),
 C65(H65), C64(H64), C63(H63), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15),
  C22(H22), C21(H21), C20(H20), C19(H19), C18(H18), C6(H6), C5(H5), C4(H4),
 C3(H3), C2(H2), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31)
4.b Fitted hexagon refined as free rotating group:
 C48(C53,C51,C52,C50,C49), C69(C74,C73,C72,C71,C70), C55(C56,C57,C58,C59,C60),
 C76(C82,C81,C80,C79,C78), C41(C42,C43,C44,C45,C46), C34(C38,C39,C37,C36,C35),
 C84(C85,C86,C87,C88,C89), C62(C67,C66,C65,C64,C63), C10(C11,C12,C13,C14,C15),
 C23(C22,C21,C20,C19,C18), C7(C6,C5,C4,C3,C2), C26(C27,C28,C29,C30,C31)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O5 O 0.0499(2) 0.78676(13) 0.49361(13) 0.0275(6) Uani 1 1 d . . . . .
O1 O 0.8910(3) 0.61907(13) 0.32841(14) 0.0274(6) Uani 1 1 d . . . . .
O3 O 0.5559(3) 0.71238(14) 0.49794(14) 0.0295(6) Uani 1 1 d . . . . .
O4 O 0.7278(2) 0.54636(13) 0.66371(14) 0.0289(6) Uani 1 1 d . . . . .
O2 O 0.3894(3) 0.87940(14) 0.32861(14) 0.0307(6) Uani 1 1 d . . . . .
O6 O 0.2182(3) 0.95617(13) 0.66431(14) 0.0327(7) Uani 1 1 d . . . . .
N9 N 0.4102(3) 0.74349(19) 0.52631(19) 0.0392(9) Uani 1 1 d . . . . .
N14 N -0.0745(3) 0.78946(18) 0.54920(18) 0.0368(9) Uani 1 1 d . . . . .
N13 N -0.1248(3) 0.78116(18) 0.48845(18) 0.0358(8) Uani 1 1 d . . . . .
N11 N 0.8719(3) 0.57777(18) 0.63315(18) 0.0366(9) Uani 1 1 d . . . . .
N10 N 0.4160(3) 0.68505(19) 0.53500(19) 0.0398(9) Uani 1 1 d . . . . .
C61 C -0.0491(3) 0.78028(17) 0.4583(2) 0.0281(8) Uani 1 1 d . . . . .
N12 N 0.8794(3) 0.51867(18) 0.64036(19) 0.0381(9) Uani 1 1 d . . . . .
C33 C 0.4932(3) 0.75745(19) 0.50458(19) 0.0295(9) Uani 1 1 d . . . . .
C40 C 0.5016(3) 0.6684(2) 0.51736(18) 0.0293(9) Uani 1 1 d . . . . .
C68 C 0.0279(3) 0.79232(17) 0.54943(19) 0.0276(8) Uani 1 1 d . . . . .
N16 N 0.3917(4) 0.9607(2) 0.6654(2) 0.0437(10) Uani 1 1 d . . . . .
C48 C 0.7337(2) 0.64772(9) 0.64776(12) 0.0302(9) Uani 1 1 d . . . . .
C53 C 0.6434(2) 0.65619(10) 0.67238(12) 0.0311(9) Uani 1 1 d G . . . .
H53 H 0.612817 0.625411 0.689961 0.037 Uiso 1 1 calc R . . . .
C51 C 0.5977(2) 0.70968(12) 0.67129(14) 0.0376(10) Uani 1 1 d G . . . .
H51 H 0.535984 0.715471 0.688118 0.045 Uiso 1 1 calc R . . . .
C52 C 0.6424(2) 0.75471(9) 0.64557(15) 0.0356(10) Uani 1 1 d G . . . .
H52 H 0.611245 0.791277 0.644819 0.043 Uiso 1 1 calc R . . . .
C50 C 0.7328(2) 0.74625(10) 0.62094(14) 0.0368(10) Uani 1 1 d G . . . .
H50 H 0.763340 0.777022 0.603362 0.044 Uiso 1 1 calc R . . . .
C49 C 0.7784(2) 0.69275(12) 0.62204(13) 0.0332(9) Uani 1 1 d G . . . .
H49 H 0.840176 0.686961 0.605204 0.040 Uiso 1 1 calc R . . . .
N15 N 0.3372(4) 0.95345(19) 0.6058(2) 0.0420(10) Uani 1 1 d . . . . .
C69 C 0.11597(18) 0.80103(13) 0.60098(10) 0.0289(8) Uani 1 1 d . . . . .
C74 C 0.2219(2) 0.79722(13) 0.59412(10) 0.0297(8) Uani 1 1 d G . . . .
H74 H 0.237280 0.788463 0.555866 0.036 Uiso 1 1 calc R . . . .
C73 C 0.30542(17) 0.80621(14) 0.64325(13) 0.0392(11) Uani 1 1 d G . . . .
H73 H 0.377843 0.803597 0.638565 0.047 Uiso 1 1 calc R . . . .
C72 C 0.2830(2) 0.81901(14) 0.69923(11) 0.0413(11) Uani 1 1 d G . . . .
H72 H 0.340028 0.825158 0.732800 0.050 Uiso 1 1 calc R . . . .
C71 C 0.1770(3) 0.82283(14) 0.70608(10) 0.0438(12) Uani 1 1 d G . . . .
H71 H 0.161649 0.831585 0.744337 0.053 Uiso 1 1 calc R . . . .
C70 C 0.09350(19) 0.81384(13) 0.65696(12) 0.0369(10) Uani 1 1 d G . . . .
H70 H 0.021083 0.816451 0.661639 0.044 Uiso 1 1 calc R . . . .
C55 C 0.7626(2) 0.44539(9) 0.67128(13) 0.0299(9) Uani 1 1 d . . . . .
C56 C 0.66329(19) 0.43478(10) 0.68573(13) 0.0310(9) Uani 1 1 d G . . . .
H56 H 0.614381 0.464973 0.686705 0.037 Uiso 1 1 calc R . . . .
C57 C 0.63557(19) 0.38001(12) 0.69876(14) 0.0344(9) Uani 1 1 d G . . . .
H57 H 0.567702 0.372759 0.708641 0.041 Uiso 1 1 calc R . . . .
C58 C 0.7071(2) 0.33583(9) 0.69734(14) 0.0338(9) Uani 1 1 d G . . . .
H58 H 0.688179 0.298395 0.706244 0.041 Uiso 1 1 calc R . . . .
C59 C 0.8064(2) 0.34644(10) 0.68289(15) 0.0369(10) Uani 1 1 d G . . . .
H59 H 0.855337 0.316245 0.681913 0.044 Uiso 1 1 calc R . . . .
C60 C 0.83416(17) 0.40121(12) 0.66985(14) 0.0342(9) Uani 1 1 d G . . . .
H60 H 0.902019 0.408459 0.659976 0.041 Uiso 1 1 calc R . . . .
N1 N 0.7829(4) 0.6224(2) 0.3942(2) 0.0320(11) Uani 0.792(5) 1 d . . P A 1
N7 N 0.2391(4) 0.9003(2) 0.3585(2) 0.0362(11) Uani 0.823(6) 1 d . . P B 1
C76 C 0.1444(2) 0.94412(13) 0.55784(11) 0.0335(9) Uani 1 1 d . . . . .
C82 C 0.0401(2) 0.95126(13) 0.56663(11) 0.0354(10) Uani 1 1 d G . . . .
H82 H 0.028110 0.962078 0.605068 0.042 Uiso 1 1 calc R . . . .
C81 C -0.04657(19) 0.94258(14) 0.51919(14) 0.0418(11) Uani 1 1 d G . . . .
H81 H -0.117821 0.947461 0.525195 0.050 Uiso 1 1 calc R . . . .
C80 C -0.0290(2) 0.92676(14) 0.46295(12) 0.0412(11) Uani 1 1 d G . . . .
H80 H -0.088261 0.920825 0.430519 0.049 Uiso 1 1 calc R . . . .
C79 C 0.0752(3) 0.91962(14) 0.45415(10) 0.0410(11) Uani 1 1 d G . . . .
H79 H 0.087229 0.908805 0.415716 0.049 Uiso 1 1 calc R . . . .
C78 C 0.1619(2) 0.92830(13) 0.50160(13) 0.0371(10) Uani 1 1 d G . . . .
H78 H 0.233161 0.923421 0.495588 0.044 Uiso 1 1 calc R . . . .
C41 C 0.5454(2) 0.61156(10) 0.51733(12) 0.0311(9) Uani 1 1 d . . . . .
C42 C 0.4959(2) 0.56689(13) 0.54087(13) 0.0375(10) Uani 1 1 d G . . . .
H42 H 0.432889 0.573379 0.556291 0.045 Uiso 1 1 calc R . . . .
C43 C 0.5388(3) 0.51274(11) 0.54184(14) 0.0426(12) Uani 1 1 d G . . . .
H43 H 0.504969 0.482214 0.557922 0.051 Uiso 1 1 calc R . . . .
C44 C 0.6310(3) 0.50325(9) 0.51927(15) 0.0412(11) Uani 1 1 d G . . . .
H44 H 0.660281 0.466237 0.519928 0.049 Uiso 1 1 calc R . . . .
C45 C 0.6805(2) 0.54791(12) 0.49573(14) 0.0388(11) Uani 1 1 d G . . . .
H45 H 0.743513 0.541425 0.480303 0.047 Uiso 1 1 calc R . . . .
C46 C 0.6376(2) 0.60207(10) 0.49476(13) 0.0344(10) Uani 1 1 d G . . . .
H46 H 0.671434 0.632591 0.478671 0.041 Uiso 1 1 calc R . . . .
C34 C 0.5252(2) 0.81336(10) 0.48782(13) 0.0299(9) Uani 1 1 d . . . . .
C38 C 0.4590(2) 0.85938(13) 0.49186(14) 0.0383(10) Uani 1 1 d G . . . .
H38 H 0.394984 0.854394 0.506740 0.046 Uiso 1 1 calc R . . . .
C39 C 0.4866(3) 0.91271(11) 0.47411(15) 0.0456(12) Uani 1 1 d G . . . .
H39 H 0.441339 0.944164 0.476869 0.055 Uiso 1 1 calc R . . . .
C37 C 0.5803(3) 0.92001(10) 0.45233(15) 0.0473(13) Uani 1 1 d G . . . .
H37 H 0.599085 0.956452 0.440205 0.057 Uiso 1 1 calc R . . . .
C36 C 0.6464(2) 0.87398(13) 0.44830(15) 0.0418(11) Uani 1 1 d G . . . .
H36 H 0.710477 0.878969 0.433413 0.050 Uiso 1 1 calc R . . . .
C35 C 0.6189(2) 0.82066(11) 0.46604(14) 0.0342(10) Uani 1 1 d G . . . .
H35 H 0.664124 0.789199 0.463284 0.041 Uiso 1 1 calc R . . . .
C84 C 0.3323(3) 0.96729(14) 0.76327(10) 0.0369(10) Uani 1 1 d . . . . .
C85 C 0.2438(2) 0.96452(15) 0.79050(13) 0.0404(11) Uani 1 1 d G . . . .
H85 H 0.174040 0.958820 0.766652 0.048 Uiso 1 1 calc R . . . .
C86 C 0.2575(3) 0.97010(16) 0.85261(14) 0.0467(12) Uani 1 1 d G . . . .
H86 H 0.197024 0.968213 0.871216 0.056 Uiso 1 1 calc R . . . .
C87 C 0.3596(3) 0.97845(16) 0.88750(10) 0.0521(15) Uani 1 1 d G . . . .
H87 H 0.368904 0.982265 0.929949 0.062 Uiso 1 1 calc R . . . .
C88 C 0.4480(2) 0.98122(16) 0.86027(15) 0.0534(15) Uani 1 1 d G . . . .
H88 H 0.517800 0.986923 0.884118 0.064 Uiso 1 1 calc R . . . .
C89 C 0.4344(2) 0.97564(15) 0.79816(15) 0.0473(12) Uani 1 1 d G . . . .
H89 H 0.494818 0.977530 0.779554 0.057 Uiso 1 1 calc R . . . .
N8 N 0.2544(4) 0.8420(2) 0.3641(2) 0.0364(11) Uani 0.823(6) 1 d . . P B 1
N2 N 0.7196(4) 0.6146(2) 0.3362(2) 0.0316(10) Uani 0.792(5) 1 d . . P A 1
C47 C 0.7817(4) 0.59186(19) 0.64733(19) 0.0310(9) Uani 1 1 d . . . . .
C54 C 0.7941(4) 0.50246(19) 0.65783(19) 0.0310(9) Uani 1 1 d . . . . .
C8 C 0.7862(4) 0.6134(2) 0.3001(2) 0.0281(10) Uani 0.792(5) 1 d . . P A 1
C62 C -0.0580(2) 0.77331(13) 0.39364(9) 0.0295(9) Uani 1 1 d . . . . .
C67 C 0.03306(18) 0.77669(13) 0.36870(12) 0.0329(9) Uani 1 1 d G . . . .
H67 H 0.100957 0.784690 0.393654 0.039 Uiso 1 1 calc R . . . .
C66 C 0.0247(2) 0.76838(14) 0.30724(12) 0.0372(10) Uani 1 1 d G . . . .
H66 H 0.086965 0.770700 0.290196 0.045 Uiso 1 1 calc R . . . .
C65 C -0.0746(3) 0.75669(13) 0.27073(10) 0.0379(10) Uani 1 1 d G . . . .
H65 H -0.080285 0.751007 0.228729 0.046 Uiso 1 1 calc R . . . .
C64 C -0.1656(2) 0.75330(13) 0.29567(12) 0.0376(10) Uani 1 1 d G . . . .
H64 H -0.233543 0.745305 0.270718 0.045 Uiso 1 1 calc R . . . .
C63 C -0.15733(18) 0.76161(13) 0.35713(13) 0.0347(10) Uani 1 1 d G . . . .
H63 H -0.219553 0.759294 0.374175 0.042 Uiso 1 1 calc R . . . .
C75 C 0.2363(4) 0.95146(18) 0.6071(2) 0.0338(9) Uani 1 1 d . . . . .
C9 C 0.8812(4) 0.6249(2) 0.3879(2) 0.0266(10) Uani 0.792(5) 1 d . . P A 1
C83 C 0.3197(4) 0.9620(2) 0.6980(2) 0.0352(10) Uani 1 1 d . . . . .
C24 C 0.3195(4) 0.9195(2) 0.3378(2) 0.0295(11) Uani 0.823(6) 1 d . . P B 1
C10 C 0.9749(2) 0.63238(14) 0.43577(12) 0.0454(9) Uani 1 1 d . . . . .
C11 C 0.9661(2) 0.63847(14) 0.49555(14) 0.0386(10) Uani 1 1 d G . . A .
H11 H 0.897917 0.635249 0.506280 0.046 Uiso 1 1 calc R . . . .
C12 C 1.0571(3) 0.64928(14) 0.53961(10) 0.0380(10) Uani 1 1 d G . . A .
H12 H 1.051104 0.653444 0.580465 0.046 Uiso 1 1 calc R . . . .
C13 C 1.1569(2) 0.65400(14) 0.52391(13) 0.0430(11) Uani 1 1 d G . . A .
H13 H 1.219075 0.661385 0.554024 0.052 Uiso 1 1 calc R . . . .
C14 C 1.1657(2) 0.64791(15) 0.46413(16) 0.0499(13) Uani 1 1 d G . . A .
H14 H 1.233859 0.651133 0.453398 0.060 Uiso 1 1 calc R . . . .
C15 C 1.0747(3) 0.63710(15) 0.42007(11) 0.0454(9) Uani 1 1 d G . . A .
H15 H 1.080673 0.632939 0.379213 0.055 Uiso 1 1 calc R . . C 1
C25 C 0.3418(4) 0.8309(2) 0.3466(2) 0.0307(11) Uani 0.823(6) 1 d . . P B 1
C23 C 0.3399(3) 0.97810(11) 0.32430(14) 0.0473(10) Uani 1 1 d . . . . .
C22 C 0.2633(2) 1.01950(15) 0.32681(15) 0.0513(14) Uani 1 1 d G . . B .
H22 H 0.197250 1.009615 0.337573 0.062 Uiso 1 1 calc R . . . .
C21 C 0.2833(3) 1.07537(13) 0.31356(16) 0.0483(13) Uani 1 1 d G . . B .
H21 H 0.230997 1.103669 0.315273 0.058 Uiso 1 1 calc R . . . .
C20 C 0.3800(3) 1.08984(11) 0.29780(16) 0.0429(12) Uani 1 1 d G . . B .
H20 H 0.393655 1.128029 0.288751 0.052 Uiso 1 1 calc R . . . .
C19 C 0.4565(2) 1.04844(15) 0.29530(16) 0.0488(13) Uani 1 1 d G . . B .
H19 H 0.522569 1.058334 0.284530 0.059 Uiso 1 1 calc R . . . .
C18 C 0.4365(3) 0.99257(13) 0.30854(15) 0.0470(13) Uani 1 1 d G . . B .
H18 H 0.488824 0.964279 0.306830 0.056 Uiso 1 1 calc R . . D 1
C7 C 0.7613(3) 0.60677(14) 0.23523(10) 0.0454(9) Uani 1 1 d . . . . .
C6 C 0.6560(3) 0.59618(15) 0.20599(14) 0.0476(13) Uani 1 1 d G . . A .
H6 H 0.601014 0.593088 0.228563 0.057 Uiso 1 1 calc R . . . .
C5 C 0.6313(2) 0.59012(15) 0.14374(14) 0.0447(12) Uani 1 1 d G . . A .
H5 H 0.559376 0.582882 0.123756 0.054 Uiso 1 1 calc R . . . .
C4 C 0.7118(3) 0.59464(15) 0.11071(10) 0.0424(12) Uani 1 1 d G . . A .
H4 H 0.694936 0.590501 0.068161 0.051 Uiso 1 1 calc R . . . .
C3 C 0.8171(2) 0.60523(15) 0.13994(14) 0.0494(13) Uani 1 1 d G . . A .
H3 H 0.872134 0.608326 0.117372 0.059 Uiso 1 1 calc R . . . .
C2 C 0.8418(2) 0.61130(15) 0.20220(14) 0.0454(9) Uani 1 1 d G . . A .
H2 H 0.913774 0.618532 0.222179 0.054 Uiso 1 1 calc R . . E 1
C26 C 0.3919(3) 0.77596(11) 0.34428(14) 0.0473(10) Uani 1 1 d . . . . .
C27 C 0.3476(2) 0.72827(14) 0.36555(14) 0.0415(11) Uani 1 1 d G . . B .
H27 H 0.282621 0.731279 0.379919 0.050 Uiso 1 1 calc R . . . .
C28 C 0.3983(3) 0.67618(11) 0.36579(15) 0.0363(10) Uani 1 1 d G . . B .
H28 H 0.368035 0.643591 0.380324 0.044 Uiso 1 1 calc R . . . .
C29 C 0.4933(3) 0.67178(12) 0.34476(17) 0.0461(12) Uani 1 1 d G . . B .
H29 H 0.528014 0.636185 0.344925 0.055 Uiso 1 1 calc R . . . .
C30 C 0.5376(2) 0.71947(16) 0.32349(17) 0.0542(15) Uani 1 1 d G . . B .
H30 H 0.602583 0.716466 0.309121 0.065 Uiso 1 1 calc R . . . .
C31 C 0.4869(3) 0.77156(13) 0.32325(15) 0.0492(13) Uani 1 1 d G . . B .
H31 H 0.517171 0.804154 0.308715 0.059 Uiso 1 1 calc R . . F 1
N4 N 1.0537(15) 0.6191(8) 0.3127(8) 0.034(4) Uani 0.208(5) 1 d . . P A 2
N3 N 0.9915(18) 0.6138(8) 0.2565(9) 0.042(5) Uani 0.208(5) 1 d . . P A 2
C1 C 0.8939(16) 0.6139(9) 0.2639(9) 0.0281(10) Uani 0.208(5) 1 d . . P A 2
C16 C 0.9947(17) 0.6246(8) 0.3515(8) 0.0266(10) Uani 0.208(5) 1 d . . P A 2
C17 C 0.436(2) 0.9330(11) 0.3079(10) 0.030(5) Uani 0.177(6) 1 d . . P B 2
N6 N 0.5241(17) 0.9229(9) 0.2910(10) 0.033(5) Uani 0.177(6) 1 d . . P B 2
N5 N 0.5370(14) 0.8655(9) 0.2965(8) 0.026(4) Uani 0.177(6) 1 d . . P B 2
C32 C 0.457(2) 0.8442(11) 0.3161(10) 0.0307(11) Uani 0.177(6) 1 d . . P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
O5 C61 1.356(5) . ?
O5 C68 1.357(5) . ?
O1 C8 1.362(6) . ?
O1 C9 1.387(6) . ?
O1 C1 1.48(2) . ?
O1 C16 1.32(2) . ?
O3 C33 1.358(5) . ?
O3 C40 1.370(5) . ?
O4 C47 1.367(5) . ?
O4 C54 1.361(5) . ?
O2 C24 1.344(6) . ?
O2 C25 1.396(6) . ?
O2 C17 1.51(2) . ?
O2 C32 1.27(3) . ?
O6 C75 1.368(5) . ?
O6 C83 1.366(6) . ?
N9 N10 1.396(6) . ?
N9 C33 1.295(6) . ?
N14 N13 1.410(6) . ?
N14 C68 1.302(6) . ?
N13 C61 1.289(6) . ?
N11 N12 1.408(6) . ?
N11 C47 1.296(6) . ?
N10 C40 1.295(6) . ?
C61 C62 1.457(5) . ?
N12 C54 1.287(6) . ?
C33 C34 1.456(5) . ?
C40 C41 1.455(5) . ?
C68 C69 1.460(5) . ?
N16 N15 1.400(6) . ?
N16 C83 1.289(7) . ?
C48 C53 1.3900 . ?
C48 C49 1.3900 . ?
C48 C47 1.456(5) . ?
C53 H53 0.9500 . ?
C53 C51 1.3900 . ?
C51 H51 0.9500 . ?
C51 C52 1.3900 . ?
C52 H52 0.9500 . ?
C52 C50 1.3900 . ?
C50 H50 0.9500 . ?
C50 C49 1.3900 . ?
C49 H49 0.9500 . ?
N15 C75 1.290(7) . ?
C69 C74 1.3900 . ?
C69 C70 1.3900 . ?
C74 H74 0.9500 . ?
C74 C73 1.3900 . ?
C73 H73 0.9500 . ?
C73 C72 1.3900 . ?
C72 H72 0.9500 . ?
C72 C71 1.3900 . ?
C71 H71 0.9500 . ?
C71 C70 1.3900 . ?
C70 H70 0.9500 . ?
C55 C56 1.3900 . ?
C55 C60 1.3900 . ?
C55 C54 1.458(5) . ?
C56 H56 0.9500 . ?
C56 C57 1.3900 . ?
C57 H57 0.9500 . ?
C57 C58 1.3900 . ?
C58 H58 0.9500 . ?
C58 C59 1.3900 . ?
C59 H59 0.9500 . ?
C59 C60 1.3900 . ?
C60 H60 0.9500 . ?
N1 N2 1.408(6) . ?
N1 C9 1.287(7) . ?
N7 N8 1.394(7) . ?
N7 C24 1.291(7) . ?
C76 C82 1.3900 . ?
C76 C78 1.3900 . ?
C76 C75 1.453(5) . ?
C82 H82 0.9500 . ?
C82 C81 1.3900 . ?
C81 H81 0.9500 . ?
C81 C80 1.3900 . ?
C80 H80 0.9500 . ?
C80 C79 1.3900 . ?
C79 H79 0.9500 . ?
C79 C78 1.3900 . ?
C78 H78 0.9500 . ?
C41 C42 1.3900 . ?
C41 C46 1.3900 . ?
C42 H42 0.9500 . ?
C42 C43 1.3900 . ?
C43 H43 0.9500 . ?
C43 C44 1.3900 . ?
C44 H44 0.9500 . ?
C44 C45 1.3900 . ?
C45 H45 0.9500 . ?
C45 C46 1.3900 . ?
C46 H46 0.9500 . ?
C34 C38 1.3900 . ?
C34 C35 1.3900 . ?
C38 H38 0.9500 . ?
C38 C39 1.3900 . ?
C39 H39 0.9500 . ?
C39 C37 1.3900 . ?
C37 H37 0.9500 . ?
C37 C36 1.3900 . ?
C36 H36 0.9500 . ?
C36 C35 1.3900 . ?
C35 H35 0.9500 . ?
C84 C85 1.3900 . ?
C84 C89 1.3900 . ?
C84 C83 1.461(5) . ?
C85 H85 0.9500 . ?
C85 C86 1.3900 . ?
C86 H86 0.9500 . ?
C86 C87 1.3900 . ?
C87 H87 0.9500 . ?
C87 C88 1.3900 . ?
C88 H88 0.9500 . ?
C88 C89 1.3900 . ?
C89 H89 0.9500 . ?
N8 C25 1.281(7) . ?
N2 C8 1.291(7) . ?
C8 C7 1.450(6) . ?
C62 C67 1.3900 . ?
C62 C63 1.3900 . ?
C67 H67 0.9500 . ?
C67 C66 1.3900 . ?
C66 H66 0.9500 . ?
C66 C65 1.3900 . ?
C65 H65 0.9500 . ?
C65 C64 1.3900 . ?
C64 H64 0.9500 . ?
C64 C63 1.3900 . ?
C63 H63 0.9500 . ?
C9 C10 1.450(6) . ?
C24 C23 1.454(6) . ?
C10 C11 1.3900 . ?
C10 C15 1.3900 . ?
C10 C16 1.986(19) . ?
C11 H11 0.9500 . ?
C11 C12 1.3900 . ?
C12 H12 0.9500 . ?
C12 C13 1.3900 . ?
C13 H13 0.9500 . ?
C13 C14 1.3900 . ?
C14 H14 0.9500 . ?
C14 C15 1.3900 . ?
C15 H15 0.9500 . ?
C15 C16 1.70(2) . ?
C25 C26 1.451(6) . ?
C23 C22 1.3900 . ?
C23 C18 1.3900 . ?
C23 C17 1.72(3) . ?
C22 H22 0.9500 . ?
C22 C21 1.3900 . ?
C21 H21 0.9500 . ?
C21 C20 1.3900 . ?
C20 H20 0.9500 . ?
C20 C19 1.3900 . ?
C19 H19 0.9500 . ?
C19 C18 1.3900 . ?
C18 H18 0.9500 . ?
C18 C17 1.41(3) . ?
C7 C6 1.3900 . ?
C7 C2 1.3900 . ?
C7 C1 1.69(2) . ?
C6 H6 0.9500 . ?
C6 C5 1.3900 . ?
C5 H5 0.9500 . ?
C5 C4 1.3900 . ?
C4 H4 0.9500 . ?
C4 C3 1.3900 . ?
C3 H3 0.9500 . ?
C3 C2 1.3900 . ?
C2 H2 0.9500 . ?
C2 C1 1.42(2) . ?
C26 C27 1.3900 . ?
C26 C31 1.3900 . ?
C26 C32 1.97(2) . ?
C27 H27 0.9500 . ?
C27 C28 1.3900 . ?
C28 H28 0.9500 . ?
C28 C29 1.3900 . ?
C29 H29 0.9500 . ?
C29 C30 1.3900 . ?
C30 H30 0.9500 . ?
C30 C31 1.3900 . ?
C31 H31 0.9500 . ?
C31 C32 1.76(3) . ?
N4 N3 1.36(3) . ?
N4 C16 1.27(3) . ?
N3 C1 1.28(3) . ?
C17 N6 1.28(3) . ?
N6 N5 1.37(3) . ?
N5 C32 1.30(3) . ?

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
C61 O5 C68 102.6(3) . . ?
C8 O1 C9 101.3(4) . . ?
C16 O1 C1 100.2(11) . . ?
C33 O3 C40 102.4(3) . . ?
C54 O4 C47 102.7(3) . . ?
C24 O2 C25 101.3(4) . . ?
C32 O2 C17 99.1(15) . . ?
C83 O6 C75 102.5(4) . . ?
C33 N9 N10 106.4(4) . . ?
C68 N14 N13 105.4(4) . . ?
C61 N13 N14 106.3(4) . . ?
C47 N11 N12 105.6(4) . . ?
C40 N10 N9 106.3(4) . . ?
O5 C61 C62 118.6(3) . . ?
N13 C61 O5 112.9(4) . . ?
N13 C61 C62 128.5(4) . . ?
C54 N12 N11 106.9(4) . . ?
O3 C33 C34 118.8(3) . . ?
N9 C33 O3 112.6(4) . . ?
N9 C33 C34 128.6(4) . . ?
O3 C40 C41 118.9(3) . . ?
N10 C40 O3 112.3(4) . . ?
N10 C40 C41 128.8(4) . . ?
O5 C68 C69 119.3(3) . . ?
N14 C68 O5 112.8(4) . . ?
N14 C68 C69 127.9(4) . . ?
C83 N16 N15 106.7(4) . . ?
C53 C48 C49 120.0 . . ?
C53 C48 C47 121.0(2) . . ?
C49 C48 C47 119.0(2) . . ?
C48 C53 H53 120.0 . . ?
C48 C53 C51 120.0 . . ?
C51 C53 H53 120.0 . . ?
C53 C51 H51 120.0 . . ?
C53 C51 C52 120.0 . . ?
C52 C51 H51 120.0 . . ?
C51 C52 H52 120.0 . . ?
C50 C52 C51 120.0 . . ?
C50 C52 H52 120.0 . . ?
C52 C50 H50 120.0 . . ?
C52 C50 C49 120.0 . . ?
C49 C50 H50 120.0 . . ?
C48 C49 H49 120.0 . . ?
C50 C49 C48 120.0 . . ?
C50 C49 H49 120.0 . . ?
C75 N15 N16 106.3(4) . . ?
C74 C69 C68 120.3(2) . . ?
C74 C69 C70 120.0 . . ?
C70 C69 C68 119.7(2) . . ?
C69 C74 H74 120.0 . . ?
C69 C74 C73 120.0 . . ?
C73 C74 H74 120.0 . . ?
C74 C73 H73 120.0 . . ?
C74 C73 C72 120.0 . . ?
C72 C73 H73 120.0 . . ?
C73 C72 H72 120.0 . . ?
C71 C72 C73 120.0 . . ?
C71 C72 H72 120.0 . . ?
C72 C71 H71 120.0 . . ?
C72 C71 C70 120.0 . . ?
C70 C71 H71 120.0 . . ?
C69 C70 H70 120.0 . . ?
C71 C70 C69 120.0 . . ?
C71 C70 H70 120.0 . . ?
C56 C55 C60 120.0 . . ?
C56 C55 C54 121.2(2) . . ?
C60 C55 C54 118.8(2) . . ?
C55 C56 H56 120.0 . . ?
C57 C56 C55 120.0 . . ?
C57 C56 H56 120.0 . . ?
C56 C57 H57 120.0 . . ?
C56 C57 C58 120.0 . . ?
C58 C57 H57 120.0 . . ?
C57 C58 H58 120.0 . . ?
C59 C58 C57 120.0 . . ?
C59 C58 H58 120.0 . . ?
C58 C59 H59 120.0 . . ?
C58 C59 C60 120.0 . . ?
C60 C59 H59 120.0 . . ?
C55 C60 H60 120.0 . . ?
C59 C60 C55 120.0 . . ?
C59 C60 H60 120.0 . . ?
C9 N1 N2 106.6(4) . . ?
C24 N7 N8 106.0(5) . . ?
C82 C76 C78 120.0 . . ?
C82 C76 C75 121.1(3) . . ?
C78 C76 C75 118.9(3) . . ?
C76 C82 H82 120.0 . . ?
C76 C82 C81 120.0 . . ?
C81 C82 H82 120.0 . . ?
C82 C81 H81 120.0 . . ?
C80 C81 C82 120.0 . . ?
C80 C81 H81 120.0 . . ?
C81 C80 H80 120.0 . . ?
C79 C80 C81 120.0 . . ?
C79 C80 H80 120.0 . . ?
C80 C79 H79 120.0 . . ?
C80 C79 C78 120.0 . . ?
C78 C79 H79 120.0 . . ?
C76 C78 H78 120.0 . . ?
C79 C78 C76 120.0 . . ?
C79 C78 H78 120.0 . . ?
C42 C41 C40 119.9(2) . . ?
C42 C41 C46 120.0 . . ?
C46 C41 C40 120.1(2) . . ?
C41 C42 H42 120.0 . . ?
C43 C42 C41 120.0 . . ?
C43 C42 H42 120.0 . . ?
C42 C43 H43 120.0 . . ?
C42 C43 C44 120.0 . . ?
C44 C43 H43 120.0 . . ?
C43 C44 H44 120.0 . . ?
C45 C44 C43 120.0 . . ?
C45 C44 H44 120.0 . . ?
C44 C45 H45 120.0 . . ?
C44 C45 C46 120.0 . . ?
C46 C45 H45 120.0 . . ?
C41 C46 H46 120.0 . . ?
C45 C46 C41 120.0 . . ?
C45 C46 H46 120.0 . . ?
C38 C34 C33 119.3(2) . . ?
C38 C34 C35 120.0 . . ?
C35 C34 C33 120.7(2) . . ?
C34 C38 H38 120.0 . . ?
C39 C38 C34 120.0 . . ?
C39 C38 H38 120.0 . . ?
C38 C39 H39 120.0 . . ?
C38 C39 C37 120.0 . . ?
C37 C39 H39 120.0 . . ?
C39 C37 H37 120.0 . . ?
C39 C37 C36 120.0 . . ?
C36 C37 H37 120.0 . . ?
C37 C36 H36 120.0 . . ?
C35 C36 C37 120.0 . . ?
C35 C36 H36 120.0 . . ?
C34 C35 H35 120.0 . . ?
C36 C35 C34 120.0 . . ?
C36 C35 H35 120.0 . . ?
C85 C84 C89 120.0 . . ?
C85 C84 C83 120.9(3) . . ?
C89 C84 C83 119.1(3) . . ?
C84 C85 H85 120.0 . . ?
C86 C85 C84 120.0 . . ?
C86 C85 H85 120.0 . . ?
C85 C86 H86 120.0 . . ?
C85 C86 C87 120.0 . . ?
C87 C86 H86 120.0 . . ?
C86 C87 H87 120.0 . . ?
C88 C87 C86 120.0 . . ?
C88 C87 H87 120.0 . . ?
C87 C88 H88 120.0 . . ?
C87 C88 C89 120.0 . . ?
C89 C88 H88 120.0 . . ?
C84 C89 H89 120.0 . . ?
C88 C89 C84 120.0 . . ?
C88 C89 H89 120.0 . . ?
C25 N8 N7 106.8(4) . . ?
C8 N2 N1 105.7(4) . . ?
O4 C47 C48 118.6(4) . . ?
N11 C47 O4 112.5(4) . . ?
N11 C47 C48 128.9(4) . . ?
O4 C54 C55 119.0(4) . . ?
N12 C54 O4 112.4(4) . . ?
N12 C54 C55 128.7(4) . . ?
O1 C8 C7 118.7(4) . . ?
N2 C8 O1 113.8(5) . . ?
N2 C8 C7 127.5(5) . . ?
C67 C62 C61 120.2(2) . . ?
C67 C62 C63 120.0 . . ?
C63 C62 C61 119.8(2) . . ?
C62 C67 H67 120.0 . . ?
C62 C67 C66 120.0 . . ?
C66 C67 H67 120.0 . . ?
C67 C66 H66 120.0 . . ?
C65 C66 C67 120.0 . . ?
C65 C66 H66 120.0 . . ?
C66 C65 H65 120.0 . . ?
C66 C65 C64 120.0 . . ?
C64 C65 H65 120.0 . . ?
C65 C64 H64 120.0 . . ?
C65 C64 C63 120.0 . . ?
C63 C64 H64 120.0 . . ?
C62 C63 H63 120.0 . . ?
C64 C63 C62 120.0 . . ?
C64 C63 H63 120.0 . . ?
O6 C75 C76 118.4(4) . . ?
N15 C75 O6 112.3(4) . . ?
N15 C75 C76 129.4(4) . . ?
O1 C9 C10 121.2(4) . . ?
N1 C9 O1 112.6(5) . . ?
N1 C9 C10 126.3(4) . . ?
O6 C83 C84 118.2(4) . . ?
N16 C83 O6 112.2(4) . . ?
N16 C83 C84 129.7(4) . . ?
O2 C24 C23 119.3(4) . . ?
N7 C24 O2 113.9(5) . . ?
N7 C24 C23 126.8(5) . . ?
C11 C10 C9 121.7(3) . . ?
C11 C10 C15 120.0 . . ?
C11 C10 C16 177.3(7) . . ?
C15 C10 C9 118.2(3) . . ?
C15 C10 C16 57.3(6) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.0 . . ?
C15 C14 H14 120.0 . . ?
C10 C15 H15 120.0 . . ?
C10 C15 C16 79.2(7) . . ?
C14 C15 C10 120.0 . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 160.8(7) . . ?
O2 C25 C26 120.4(4) . . ?
N8 C25 O2 112.0(5) . . ?
N8 C25 C26 127.6(5) . . ?
C22 C23 C24 120.5(3) . . ?
C22 C23 C18 120.0 . . ?
C22 C23 C17 168.7(8) . . ?
C18 C23 C24 119.5(3) . . ?
C18 C23 C17 52.7(8) . . ?
C23 C22 H22 120.0 . . ?
C23 C22 C21 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C21 H21 120.0 . . ?
C20 C21 C22 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C20 H20 120.0 . . ?
C19 C20 C21 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C19 H19 120.0 . . ?
C20 C19 C18 120.0 . . ?
C18 C19 H19 120.0 . . ?
C23 C18 H18 120.0 . . ?
C23 C18 C17 75.7(10) . . ?
C19 C18 C23 120.0 . . ?
C19 C18 H18 120.0 . . ?
C19 C18 C17 161.7(10) . . ?
C6 C7 C8 119.6(3) . . ?
C6 C7 C2 120.0 . . ?
C6 C7 C1 172.4(7) . . ?
C2 C7 C8 120.4(3) . . ?
C2 C7 C1 54.0(7) . . ?
C7 C6 H6 120.0 . . ?
C7 C6 C5 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C4 H4 120.0 . . ?
C5 C4 C3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C3 H3 120.0 . . ?
C4 C3 C2 120.0 . . ?
C2 C3 H3 120.0 . . ?
C7 C2 H2 120.0 . . ?
C7 C2 C1 73.7(8) . . ?
C3 C2 C7 120.0 . . ?
C3 C2 H2 120.0 . . ?
C3 C2 C1 165.4(8) . . ?
C27 C26 C25 120.1(3) . . ?
C27 C26 C31 120.0 . . ?
C27 C26 C32 178.6(7) . . ?
C31 C26 C25 119.8(3) . . ?
C31 C26 C32 60.1(8) . . ?
C26 C27 H27 120.0 . . ?
C26 C27 C28 120.0 . . ?
C28 C27 H27 120.0 . . ?
C27 C28 H28 120.0 . . ?
C29 C28 C27 120.0 . . ?
C29 C28 H28 120.0 . . ?
C28 C29 H29 120.0 . . ?
C30 C29 C28 120.0 . . ?
C30 C29 H29 120.0 . . ?
C29 C30 H30 120.0 . . ?
C29 C30 C31 120.0 . . ?
C31 C30 H30 120.0 . . ?
C26 C31 H31 120.0 . . ?
C26 C31 C32 76.7(8) . . ?
C30 C31 C26 120.0 . . ?
C30 C31 H31 120.0 . . ?
C30 C31 C32 163.3(8) . . ?
C16 N4 N3 110.1(19) . . ?
C1 N3 N4 105.7(18) . . ?
O1 C1 C7 99.5(11) . . ?
C2 C1 O1 151.4(16) . . ?
C2 C1 C7 52.2(7) . . ?
N3 C1 O1 110.4(17) . . ?
N3 C1 C7 149.8(18) . . ?
N3 C1 C2 98.1(16) . . ?
O1 C16 C10 94.5(11) . . ?
O1 C16 C15 137.9(14) . . ?
C15 C16 C10 43.4(4) . . ?
N4 C16 O1 113.3(17) . . ?
N4 C16 C10 151.8(18) . . ?
N4 C16 C15 108.8(17) . . ?
O2 C17 C23 96.5(13) . . ?
C18 C17 O2 146.7(19) . . ?
C18 C17 C23 51.6(9) . . ?
N6 C17 O2 111(2) . . ?
N6 C17 C23 152(2) . . ?
N6 C17 C18 100.7(18) . . ?
C17 N6 N5 105(2) . . ?
C32 N5 N6 109.2(19) . . ?
O2 C32 C26 96.9(14) . . ?
O2 C32 C31 140.0(17) . . ?
O2 C32 N5 116(2) . . ?
C31 C32 C26 43.2(6) . . ?
N5 C32 C26 147(2) . . ?
N5 C32 C31 103.8(19) . . ?

_olex2_exptl_crystal_mounting_method 
'Mounted by acrylic glue on the glass stick'
_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 2.099
_oxdiff_exptl_absorpt_empirical_full_min 0.664
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_anna_vlad240_3
_database_code_depnum_ccdc_archive 'CCDC 1875721'
_audit_update_record             
;
2018-10-28 deposited with the CCDC.	2019-02-12 downloaded from the CCDC.
;
_audit_creation_date             2018-10-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
alexaks05@rambler.ru
''
radioanimation@rambler.ru
''
mrubin@ku.edu
_publ_section_exptl              
;
Any special experimental details
;
_chemical_name_common            ?
_chemical_name_systematic        
2-(2,4-dichlorophenyl)-5-methyl-1,3,4-oxadiazole
_chemical_formula_moiety         'C9 H6 Cl2 N2 O'
_chemical_formula_sum            'C9 H6 Cl2 N2 O'
_chemical_formula_weight         229.06
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'
Cl Cl 0.3639 0.7018 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.5227(2)
_cell_length_b                   3.96920(10)
_cell_length_c                   20.5396(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.366(2)
_cell_angle_gamma                90
_cell_volume                     937.78(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8087
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.6530
_cell_measurement_theta_min      4.2170
_shelx_estimated_absorpt_T_max   0.411
_shelx_estimated_absorpt_T_min   0.111
_exptl_absorpt_coefficient_mu    5.947
_exptl_absorpt_correction_T_max  0.915
_exptl_absorpt_correction_T_min  0.784
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             464
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -3 2 0.2985
7 0 6 0.0703
0 3 -3 0.3354
-6 0 -6 0.0764
-5 0 11 0.1204
-1 3 2 0.3144
5 0 -11 0.1222
-3 -2 0 0.2879
2 0 13 0.1167
-2 -2 -10 0.2774
-2 0 -13 0.1234
4 0 -12 0.1153
5 2 -7 0.2691
6 0 -9 0.1282

_exptl_crystal_preparation       'Was prepared from nitrocompound and hydrazide'
_exptl_crystal_recrystallization_method 
'Crystallized by evaporation of saturated solution'
_exptl_crystal_size_max          0.658
_exptl_crystal_size_mid          0.256
_exptl_crystal_size_min          0.182
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
-0.2709 -2.5349 2.3215 -0.0242 0.0407 0.9989
6.5677 0.1023 5.6689 -0.4775 0.8779 -0.0361
-0.3371 2.5120 -2.8328 0.0682 -0.1215 -0.9902
-6.4715 0.2190 -5.9088 0.4760 -0.8748 -0.0905
-4.8734 -0.0886 10.5995 -0.7449 -0.6376 0.1963
-1.1102 2.5291 1.6630 -0.2609 -0.2210 -0.9397
4.8745 0.0804 -10.5997 0.7454 0.6380 -0.1932
-3.2181 -2.3241 0.0991 0.1514 -0.3606 0.9204
1.6489 0.0117 12.8119 -0.9651 0.2311 0.1229
-1.7863 -1.5179 -10.0858 0.8505 -0.2026 0.4853
-1.6033 0.1315 -12.8172 0.9569 -0.2293 -0.1782
3.6131 -0.0250 -12.0335 0.8677 0.4716 -0.1572
4.6230 1.5026 -7.4969 0.4348 0.5654 -0.7009
5.9488 -0.0612 -8.6893 0.6034 0.7872 -0.1275

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9403
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.941
_diffrn_reflns_theta_min         4.295
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -66.00  33.00   1.00    1.00    --  -41.35  38.00 -30.00   99
  2  ω    -66.00  33.00   1.00    1.00    --  -41.35  38.00-120.00   99
  3  ω     23.00  97.00   1.00    1.00    --   41.35-125.00-180.00   74
  4  ω     36.00 140.00   1.00    4.00    --  112.00 -30.00-120.00  104
  5  ω     84.00 178.00   1.00    4.00    --  112.00  30.00-150.00   94
  6  ω     36.00 116.00   1.00    4.00    --  112.00-111.00 150.00   80
  7  ω     86.00 178.00   1.00    4.00    --  112.00  45.00  30.00   92
  8  ω     57.00 151.00   1.00    4.00    --  112.00 178.00   0.00   94
  9  ω     57.00 151.00   1.00    4.00    --  112.00 178.00 -30.00   94
 10  ω     40.00 141.00   1.00    4.00    --  112.00 -61.00 -90.00  101
 11  ω     59.00 178.00   1.00    4.00    --  112.00  15.00 -30.00  119
 12  ω    100.00 178.00   1.00    4.00    --  112.00 111.00-150.00   78
 13  ω   -117.00  -9.00   1.00    1.00    --  -41.35 -77.00  90.00  108
 14  ω   -113.00 -13.00   1.00    1.00    --  -41.35 -57.00 -60.00  100
 15  ω   -117.00  -9.00   1.00    1.00    --  -41.35 -77.00-150.00  108
 16  ω     83.00 178.00   1.00    4.00    --  112.00  61.00-120.00   95
 17  ω     79.00 178.00   1.00    4.00    --  112.00  77.00 -30.00   99
 18  ω     86.00 178.00   1.00    4.00    --  112.00  45.00 150.00   92
 19  ω     83.00 174.00   1.00    4.00    --  112.00  61.00  60.00   91
 20  ω     84.00 178.00   1.00    4.00    --  112.00  30.00 120.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0076786000
_diffrn_orient_matrix_UB_12      -0.0576720000
_diffrn_orient_matrix_UB_13      -0.0742891000
_diffrn_orient_matrix_UB_21      0.1333482000
_diffrn_orient_matrix_UB_22      -0.0294562000
_diffrn_orient_matrix_UB_23      0.0009055000
_diffrn_orient_matrix_UB_31      -0.0091314000
_diffrn_orient_matrix_UB_32      -0.3828914000
_diffrn_orient_matrix_UB_33      0.0111201000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1917
_reflns_number_total             1940
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.0115(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1940
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0325
_refine_ls_restrained_S_all      1.087
_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)+(0.0540P)²+0.4398P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.0891
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C5(H5), C8(H8)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Cl2 Cl 0.18999(3) 0.76099(10) 0.32754(2) 0.02523(16) Uani 1 1 d . . . . .
Cl1 Cl 0.63731(3) 0.70674(11) 0.27770(2) 0.02664(16) Uani 1 1 d . . . . .
O1 O 0.76782(8) 0.4088(3) 0.38754(5) 0.0217(3) Uani 1 1 d . . . . .
N1 N 0.81025(11) 0.0635(4) 0.46961(6) 0.0243(3) Uani 1 1 d . . . . .
N2 N 0.68823(10) 0.0872(4) 0.46035(6) 0.0226(3) Uani 1 1 d . . . . .
C3 C 0.55371(11) 0.4098(4) 0.38713(7) 0.0177(3) Uani 1 1 d . . . . .
C7 C 0.34750(12) 0.4327(4) 0.40720(7) 0.0203(3) Uani 1 1 d . . . . .
H7 H 0.284981 0.377264 0.433396 0.024 Uiso 1 1 calc R . . . .
C2 C 0.66835(13) 0.2940(4) 0.41232(7) 0.0183(3) Uani 1 1 d . . . . .
C6 C 0.32873(12) 0.6173(4) 0.35030(7) 0.0196(3) Uani 1 1 d . . . . .
C5 C 0.41813(13) 0.6974(4) 0.31096(7) 0.0199(3) Uani 1 1 d . . . . .
H5 H 0.403019 0.821885 0.271872 0.024 Uiso 1 1 calc R . . . .
C8 C 0.45980(13) 0.3316(4) 0.42476(7) 0.0199(3) Uani 1 1 d . . . . .
H8 H 0.473770 0.204851 0.463663 0.024 Uiso 1 1 calc R . . . .
C4 C 0.53030(12) 0.5932(4) 0.32943(7) 0.0185(3) Uani 1 1 d . . . . .
C1 C 0.85196(13) 0.2546(4) 0.42634(8) 0.0217(3) Uani 1 1 d . . . . .
C9 C 0.97463(13) 0.3247(5) 0.41347(9) 0.0300(4) Uani 1 1 d . . . . .
H9A H 0.988824 0.260602 0.368555 0.045 Uiso 1 1 calc GR . . . .
H9B H 1.025865 0.194442 0.443781 0.045 Uiso 1 1 calc GR . . . .
H9C H 0.990443 0.565630 0.419552 0.045 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
Cl2 C6 1.7354(14) . ?
Cl1 C4 1.7339(14) . ?
O1 C2 1.3596(18) . ?
O1 C1 1.3635(17) . ?
N1 N2 1.4109(16) . ?
N1 C1 1.283(2) . ?
N2 C2 1.293(2) . ?
C3 C2 1.4642(19) . ?
C3 C8 1.401(2) . ?
C3 C4 1.403(2) . ?
C7 H7 0.9500 . ?
C7 C6 1.385(2) . ?
C7 C8 1.382(2) . ?
C6 C5 1.383(2) . ?
C5 H5 0.9500 . ?
C5 C4 1.389(2) . ?
C8 H8 0.9500 . ?
C1 C9 1.480(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?

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 O1 C1 102.52(12) . . ?
C1 N1 N2 106.13(12) . . ?
C2 N2 N1 106.01(12) . . ?
C8 C3 C2 116.46(13) . . ?
C8 C3 C4 117.67(13) . . ?
C4 C3 C2 125.86(13) . . ?
C6 C7 H7 120.9 . . ?
C8 C7 H7 120.9 . . ?
C8 C7 C6 118.10(13) . . ?
O1 C2 C3 121.70(13) . . ?
N2 C2 O1 112.50(13) . . ?
N2 C2 C3 125.77(14) . . ?
C7 C6 Cl2 119.78(11) . . ?
C5 C6 Cl2 118.23(12) . . ?
C5 C6 C7 121.98(13) . . ?
C6 C5 H5 120.5 . . ?
C6 C5 C4 119.02(14) . . ?
C4 C5 H5 120.5 . . ?
C3 C8 H8 118.9 . . ?
C7 C8 C3 122.22(14) . . ?
C7 C8 H8 118.9 . . ?
C3 C4 Cl1 122.96(11) . . ?
C5 C4 Cl1 116.05(11) . . ?
C5 C4 C3 120.99(13) . . ?
O1 C1 C9 117.71(14) . . ?
N1 C1 O1 112.82(14) . . ?
N1 C1 C9 129.47(15) . . ?
C1 C9 H9A 109.5 . . ?
C1 C9 H9B 109.5 . . ?
C1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

_olex2_date_sample_data_collection 2018-04-06
_olex2_exptl_crystal_mounting_method 
'Mounted by acrylic glue on the glass stick'
_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 3.893
_oxdiff_exptl_absorpt_empirical_full_min 0.579
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_anna_vlad229_5
_database_code_depnum_ccdc_archive 'CCDC 1875723'
_audit_update_record             
;
2018-10-28 deposited with the CCDC.	2019-02-12 downloaded from the CCDC.
;
_audit_creation_date             2018-10-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
alexaks05@rambler.ru
''
radioanimation@rambler.ru
''
mrubin@ku.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H7 N3 O'
_chemical_formula_sum            'C8 H7 N3 O'
_chemical_formula_weight         161.17
_chemical_absolute_configuration .
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.38130(10)
_cell_length_b                   19.4244(4)
_cell_length_c                   7.4718(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.454(2)
_cell_angle_gamma                90
_cell_volume                     762.64(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11268
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.0650
_cell_measurement_theta_min      4.4790
_shelx_estimated_absorpt_T_max   0.883
_shelx_estimated_absorpt_T_min   0.673
_exptl_absorpt_coefficient_mu    0.811
_exptl_absorpt_correction_T_max  0.913
_exptl_absorpt_correction_T_min  0.782
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             336
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 11 -2 0.0769
2 11 -1 0.0709
3 -1 2 0.2908
2 1 -4 0.0761
-1 -11 2 0.1066
-1 -11 2 0.0969
-3 0 -2 0.2378
-1 9 -3 0.1559
3 6 1 0.1904
1 11 -2 0.0535
-3 -5 2 0.1685
-2 -6 4 0.1047
-3 6 1 0.1962
-1 8 4 0.0955
2 -8 -3 0.0912
0 -12 0 0.0857
0 13 0 0.0627
-2 2 4 0.0951

_exptl_crystal_size_max          0.531
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.157
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
0.2649 10.9165 -2.4234 0.2185 0.9157 0.3372
1.5633 11.0284 -1.3552 0.2306 0.9625 -0.1429
2.5957 -0.7822 2.3794 0.0042 0.0098 -0.9999
2.2398 0.8462 -4.2905 -0.7254 0.6872 0.0408
-1.0906 -11.3018 1.8203 -0.2324 -0.9716 -0.0445
-1.1831 -11.2808 1.7369 -0.2327 -0.9725 -0.0091
-2.6281 0.4620 -2.3291 -0.0108 -0.0374 0.9992
-0.9025 8.7982 -2.8947 0.1676 0.7058 0.6883
2.8032 5.8211 0.9534 0.1367 0.5651 -0.8136
0.9489 11.3070 -1.9410 0.2314 0.9680 0.0975
-3.1685 -4.5988 1.9489 0.3303 -0.7981 0.5040
-2.0404 -5.8790 3.7587 0.3831 -0.9226 -0.0454
-3.0438 6.1659 0.7457 0.7101 -0.0193 0.7039
-1.4779 7.6816 3.6160 0.9956 -0.0251 -0.0904
1.6886 -7.7834 -3.4419 -0.9996 0.0254 0.0117
-0.4315 -12.4916 -0.1379 -0.6071 -0.7926 0.0574
0.1809 12.5910 -0.0929 0.6077 0.7932 0.0394
-2.1589 1.7683 4.3086 0.8520 -0.5213 -0.0490

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            18612
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.173
_diffrn_reflns_theta_min         4.553
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -114.00 -59.00   0.50    1.00    --  -41.35-147.00  25.00  110
  2  ω    -96.00  -2.00   0.50    1.00    --  -41.35 125.00 -90.00  188
  3  ω   -108.00 -13.00   0.50    1.00    --  -41.35 147.00  75.00  190
  4  ω     23.00  97.00   0.50    1.00    --   41.35-125.00-168.00  148
  5  ω     35.00 112.00   0.50    1.00    --   41.35-147.00  25.00  154
  6  ω     39.00 121.00   0.50    3.07    --  112.00-125.00-168.00  164
  7  ω     81.00 174.00   0.50    3.07    --  112.00 147.00  75.00  186
  8  ω     39.00 133.00   0.50    3.07    --  112.00-147.00  25.00  188
  9  ω     94.00 178.00   0.50    3.07    --  112.00 125.00 -90.00  168
 10  ω   -116.00 -17.00   0.50    1.00    --  -41.35 -38.00-180.00  198
 11  ω   -113.00 -13.00   0.50    1.00    --  -41.35 -57.00  90.00  200
 12  ω     23.00  97.00   0.50    1.00    --   41.35-125.00  30.00  148
 13  ω     17.00 116.00   0.50    1.00    --   41.35  38.00  90.00  198
 14  ω    100.00 178.00   0.50    3.07    --  112.00 111.00 120.00  156
 15  ω     57.00 151.00   0.50    3.07    --  112.00 178.00  30.00  188
 16  ω     39.00 138.00   0.50    3.07    --  112.00 -45.00 -30.00  198
 17  ω     36.00 140.00   0.50    3.07    --  112.00 -30.00  60.00  208
 18  ω     40.00 141.00   0.50    3.07    --  112.00 -61.00 150.00  202
 19  ω     57.00 151.00   0.50    3.07    --  112.00 178.00 -30.00  188
 20  ω     36.00 116.00   0.50    3.07    --  112.00-111.00 120.00  160
 21  ω     83.00 178.00   0.50    3.07    --  112.00  61.00-180.00  190
 22  ω     57.00 151.00   0.50    3.07    --  112.00 178.00 150.00  188
 23  ω     86.00 178.00   0.50    3.07    --  112.00  45.00  60.00  184
 24  ω     36.00 116.00   0.50    3.07    --  112.00-111.00  30.00  160
 25  ω     29.00 109.00   0.50    3.07    --  112.00 -94.00   0.00  160
 26  ω     57.00 151.00   0.50    3.07    --  112.00 178.00 -60.00  188
 27  ω     83.00 178.00   0.50    3.07    --  112.00  61.00   0.00  190
 28  ω    100.00 178.00   0.50    3.07    --  112.00 111.00-120.00  156
 29  ω    100.00 178.00   0.50    3.07    --  112.00 111.00  60.00  156
 30  ω     29.00 109.00   0.50    3.07    --  112.00 -94.00  30.00  160
 31  ω   -117.00  -9.00   0.50    1.00    --  -41.35 -77.00 150.00  216
 32  ω   -113.00 -13.00   0.50    1.00    --  -41.35 -57.00 -90.00  200
 33  ω   -117.00  -9.00   0.50    1.00    --  -41.35 -77.00 120.00  216
 34  ω   -117.00  -9.00   0.50    1.00    --  -41.35 -77.00 -90.00  216
 35  ω   -113.00 -13.00   0.50    1.00    --  -41.35 -57.00 -60.00  200
 36  ω   -117.00  -9.00   0.50    1.00    --  -41.35 -77.00  30.00  216
 37  ω   -117.00  -9.00   0.50    1.00    --  -41.35 -77.00-120.00  216
 38  ω      1.00  82.00   0.50    1.00    --   41.35 -99.00-120.00  162
 39  ω      1.00  82.00   0.50    1.00    --   41.35 -99.00  90.00  162
 40  ω     83.00 178.00   0.50    3.07    --  112.00  61.00-150.00  190
 41  ω     83.00 178.00   0.50    3.07    --  112.00  61.00  90.00  190
 42  ω     86.00 178.00   0.50    3.07    --  112.00  45.00 -30.00  184
 43  ω     83.00 178.00   0.50    3.07    --  112.00  61.00 120.00  190
 44  ω     83.00 178.00   0.50    3.07    --  112.00  61.00 150.00  190
 45  ω     59.00 178.00   0.50    3.07    --  112.00  15.00 -60.00  238
 46  ω     83.00 178.00   0.50    3.07    --  112.00  61.00 -90.00  190
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0995809000
_diffrn_orient_matrix_UB_12      0.0506357000
_diffrn_orient_matrix_UB_13      0.1270612000
_diffrn_orient_matrix_UB_21      0.1068177000
_diffrn_orient_matrix_UB_22      0.0607780000
_diffrn_orient_matrix_UB_23      -0.0924096000
_diffrn_orient_matrix_UB_31      -0.2541759000
_diffrn_orient_matrix_UB_32      0.0057396000
_diffrn_orient_matrix_UB_33      -0.1410792000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.931
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                3080
_reflns_number_total             3181
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.117
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.4(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3181
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0309
_refine_ls_restrained_S_all      1.047
_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)+(0.0501P)²+0.0413P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.0845
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.6(2)
 0.4(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C12(H12), C6(H6), C15(H15), C5(H5), C13(H13), C14(H14)
3.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O2 O 0.2659(3) 0.57473(7) 0.04362(18) 0.0500(3) Uani 1 1 d . . . . .
O1 O 0.2347(3) 0.42324(7) 0.59303(19) 0.0525(3) Uani 1 1 d . . . . .
N2 N 0.6661(3) 0.56546(10) 0.1862(3) 0.0606(5) Uani 1 1 d . . . . .
N4 N 0.6315(3) 0.42879(11) 0.7433(3) 0.0624(5) Uani 1 1 d . . . . .
N3 N 0.5484(4) 0.36014(10) 0.7446(3) 0.0654(5) Uani 1 1 d . . . . .
N006 N 0.5500(4) 0.34835(10) 0.2577(3) 0.0661(5) Uani 1 1 d . . . . .
N007 N 0.6178(4) 0.64851(11) 0.6500(3) 0.0678(5) Uani 1 1 d . . . . .
N1 N 0.6124(4) 0.63540(10) 0.1414(3) 0.0632(5) Uani 1 1 d . . . . .
C11 C 0.4237(4) 0.53682(10) 0.6132(3) 0.0477(4) Uani 1 1 d . . . . .
C3 C 0.4036(3) 0.45966(10) 0.1420(2) 0.0461(4) Uani 1 1 d . . . . .
C10 C 0.4429(3) 0.46348(11) 0.6537(3) 0.0490(4) Uani 1 1 d . . . . .
C2 C 0.4569(3) 0.53262(10) 0.1275(2) 0.0462(4) Uani 1 1 d . . . . .
C4 C 0.1688(4) 0.43231(11) 0.0609(3) 0.0542(4) Uani 1 1 d . . . . .
H4 H 0.040236 0.460341 -0.003854 0.065 Uiso 1 1 calc R . . . .
C9 C 0.3165(4) 0.35952(12) 0.6556(3) 0.0553(5) Uani 1 1 d . . . . .
C7 C 0.5863(4) 0.41543(12) 0.2403(3) 0.0564(5) Uani 1 1 d . . . . .
H7 H 0.742933 0.433880 0.297091 0.068 Uiso 1 1 calc R . . . .
C12 C 0.2057(4) 0.56469(12) 0.5037(3) 0.0547(5) Uani 1 1 d . . . . .
H12 H 0.067363 0.536810 0.454472 0.066 Uiso 1 1 calc R . . . .
C6 C 0.3231(5) 0.32311(13) 0.1757(3) 0.0615(5) Uani 1 1 d . . . . .
H6 H 0.294717 0.276159 0.185321 0.074 Uiso 1 1 calc R . . . .
C15 C 0.6243(4) 0.58130(13) 0.6825(3) 0.0589(5) Uani 1 1 d . . . . .
H15 H 0.771138 0.562871 0.755684 0.071 Uiso 1 1 calc R . . . .
C1 C 0.3780(4) 0.63800(11) 0.0589(3) 0.0537(4) Uani 1 1 d . . . . .
C5 C 0.1292(4) 0.36287(12) 0.0780(3) 0.0608(5) Uani 1 1 d . . . . .
H5 H -0.026426 0.343114 0.024161 0.073 Uiso 1 1 calc R . . . .
C13 C 0.1980(4) 0.63422(12) 0.4693(3) 0.0620(5) Uani 1 1 d . . . . .
H13 H 0.054212 0.654271 0.396503 0.074 Uiso 1 1 calc R . . . .
C14 C 0.4069(5) 0.67367(12) 0.5446(4) 0.0649(6) Uani 1 1 d . . . . .
H14 H 0.399804 0.720667 0.520282 0.078 Uiso 1 1 calc R . . . .
C16 C 0.1356(5) 0.30165(13) 0.6166(4) 0.0691(6) Uani 1 1 d . . . . .
H16A H -0.010938 0.311542 0.666146 0.104 Uiso 1 1 calc GR . . . .
H16B H 0.216064 0.260433 0.671718 0.104 Uiso 1 1 calc GR . . . .
H16C H 0.083747 0.295306 0.486416 0.104 Uiso 1 1 calc GR . . . .
C8 C 0.2185(5) 0.69795(12) -0.0121(4) 0.0699(6) Uani 1 1 d . . . . .
H8A H 0.144493 0.691164 -0.139694 0.105 Uiso 1 1 calc GR . . . .
H8B H 0.321523 0.738756 0.002749 0.105 Uiso 1 1 calc GR . . . .
H8C H 0.085676 0.702910 0.054585 0.105 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
O2 C2 1.357(2) . ?
O2 C1 1.363(2) . ?
O1 C10 1.361(2) . ?
O1 C9 1.362(3) . ?
N2 N1 1.414(3) . ?
N2 C2 1.286(3) . ?
N4 N3 1.407(3) . ?
N4 C10 1.280(3) . ?
N3 C9 1.281(3) . ?
N006 C7 1.328(3) . ?
N006 C6 1.336(3) . ?
N007 C15 1.327(3) . ?
N007 C14 1.327(3) . ?
N1 C1 1.280(3) . ?
C11 C10 1.456(3) . ?
C11 C12 1.387(3) . ?
C11 C15 1.393(3) . ?
C3 C2 1.454(3) . ?
C3 C4 1.384(3) . ?
C3 C7 1.390(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.376(3) . ?
C9 C16 1.474(3) . ?
C7 H7 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.374(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.375(3) . ?
C15 H15 0.9300 . ?
C1 C8 1.476(3) . ?
C5 H5 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.376(3) . ?
C14 H14 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

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 O2 C1 103.14(15) . . ?
C10 O1 C9 103.06(16) . . ?
C2 N2 N1 106.08(18) . . ?
C10 N4 N3 106.54(18) . . ?
C9 N3 N4 106.31(18) . . ?
C7 N006 C6 117.01(19) . . ?
C15 N007 C14 117.1(2) . . ?
C1 N1 N2 106.36(18) . . ?
C12 C11 C10 121.17(18) . . ?
C12 C11 C15 117.8(2) . . ?
C15 C11 C10 121.03(18) . . ?
C4 C3 C2 121.15(17) . . ?
C4 C3 C7 117.96(19) . . ?
C7 C3 C2 120.89(17) . . ?
O1 C10 C11 118.46(17) . . ?
N4 C10 O1 112.0(2) . . ?
N4 C10 C11 129.52(19) . . ?
O2 C2 C3 118.69(16) . . ?
N2 C2 O2 112.25(18) . . ?
N2 C2 C3 129.05(18) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 C3 118.74(19) . . ?
C5 C4 H4 120.6 . . ?
O1 C9 C16 118.32(19) . . ?
N3 C9 O1 112.1(2) . . ?
N3 C9 C16 129.6(2) . . ?
N006 C7 C3 123.8(2) . . ?
N006 C7 H7 118.1 . . ?
C3 C7 H7 118.1 . . ?
C11 C12 H12 120.6 . . ?
C13 C12 C11 118.8(2) . . ?
C13 C12 H12 120.6 . . ?
N006 C6 H6 118.3 . . ?
N006 C6 C5 123.5(2) . . ?
C5 C6 H6 118.3 . . ?
N007 C15 C11 123.7(2) . . ?
N007 C15 H15 118.2 . . ?
C11 C15 H15 118.2 . . ?
O2 C1 C8 117.94(19) . . ?
N1 C1 O2 112.16(19) . . ?
N1 C1 C8 129.9(2) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 C4 119.0(2) . . ?
C6 C5 H5 120.5 . . ?
C12 C13 H13 120.6 . . ?
C12 C13 C14 118.8(2) . . ?
C14 C13 H13 120.6 . . ?
N007 C14 C13 123.8(2) . . ?
N007 C14 H14 118.1 . . ?
C13 C14 H14 118.1 . . ?
C9 C16 H16A 109.5 . . ?
C9 C16 H16B 109.5 . . ?
C9 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C1 C8 H8A 109.5 . . ?
C1 C8 H8B 109.5 . . ?
C1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_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 2.531
_oxdiff_exptl_absorpt_empirical_full_min 0.610
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.6(2)
2 0.4(2)

