#------------------------------------------------------------------------------
#$Date: 2023-07-05 12:03:58 +0300 (Wed, 05 Jul 2023) $
#$Revision: 284859 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/16/7131639.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_7131639
loop_
_publ_author_name
'Sun, Weiqiang'
'Cui, Xueli'
'Qu, Jing'
'Cai, Xiaojia'
'Hu, Jinhui'
'Xiong, Zhuang'
'Guo, Suqin'
'Xu, Jun'
'Chen, Wen-Hua'
'Wu, Jia-Qiang'
_publ_section_title
;
 Facile access to 2-hydroxy-2-substituted indole-3-ones via a
 copper-catalyzed oxidative cyclization of 2-arylethynylanilines.
;
_journal_issue                   47
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7228
_journal_page_last               7231
_journal_paper_doi               10.1039/d3cc01390a
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C23 H19 N O3'
_chemical_formula_sum            'C23 H19 N O3'
_chemical_formula_weight         357.39
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-01-23
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2023-01-23 deposited with the CCDC.	2023-05-15 downloaded from the CCDC.
;
_cell_angle_alpha                90.215(2)
_cell_angle_beta                 96.665(2)
_cell_angle_gamma                106.787(2)
_cell_formula_units_Z            4
_cell_length_a                   7.90540(10)
_cell_length_b                   13.1683(3)
_cell_length_c                   19.1538(4)
_cell_measurement_reflns_used    10294
_cell_measurement_temperature    296.89(18)
_cell_measurement_theta_max      77.3780
_cell_measurement_theta_min      4.2670
_cell_volume                     1894.59(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      296.89(18)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -112.00 -38.00   0.50    2.11    --  -48.38 -35.00 -45.00  148
  2  ω     37.00 104.00   0.50    2.11    --   48.38  35.00 111.00  134
  3  ω     -9.00  40.00   0.50    2.11    --   48.38 -35.00 -45.00   98
  4  ω   -164.00 -87.00   0.50    8.45    --  -91.75 -35.00 -45.00  154
  5  ω    139.00 173.00   0.50    8.45    --  109.06  35.00 111.00   68
  6  ω     98.00 124.00   0.50    8.45    --  109.06  35.00 111.00   52
  7  ω    -10.00  27.00   0.50    2.11    --  -48.38  19.00-120.00   74
  8  ω    -39.00   0.00   0.50    2.11    --  -48.38  35.00 111.00   78
  9  ω    -19.00   8.00   0.50    2.11    --  -48.38  19.00-150.00   54
 10  ω    -61.00  13.00   0.50    2.11    --  -48.38  57.00 150.00  148
 11  ω   -101.00 -75.00   0.50    2.11    --  -48.38-125.00 -90.00   52
 12  ω    -13.00  42.00   0.50    2.11    --   48.38 -38.00-180.00  110
 13  ω    -85.00 -23.00   0.50    8.45    --  -91.75 125.00 -30.00  124
 14  ω   -120.00 -87.00   0.50    8.45    --  -91.75-125.00 150.00   66
 15  ω   -162.00-132.00   0.50    8.45    --  -91.75-125.00 150.00   60
 16  ω   -165.00 -80.00   0.50    8.45    --  -91.75 -19.00-180.00  170
 17  ω   -163.00 -79.00   0.50    8.45    --  -91.75 -57.00 120.00  168
 18  ω    -81.00 -28.00   0.50    8.45    --  -91.75  77.00  60.00  106
 19  ω    -62.00 -23.00   0.50    8.45    --  -91.75 125.00-180.00   78
 20  ω   -145.00 -81.00   0.50    8.45    --  -91.75 -57.00  90.00  128
 21  ω    -69.00 -28.00   0.50    8.45    --  -91.75 125.00-150.00   82
 22  ω     98.00 123.00   0.50    8.45    --  109.06  19.00-180.00   50
 23  ω     39.00  83.00   0.50    8.45    --  109.06 -99.00-150.00   88
 24  ω     37.00  65.00   0.50    8.45    --  109.06 -57.00  90.00   56
 25  ω     38.00  73.00   0.50    8.45    --  109.06 -77.00 -60.00   70
 26  ω     86.00 111.00   0.50    8.45    --  109.06-125.00  30.00   50
 27  ω    103.00 170.00   0.50    8.45    --  109.06  19.00  30.00  134
 28  ω     37.00 100.00   0.50    8.45    --  109.06 -99.00  60.00  126
 29  ω     40.00  73.00   0.50    8.45    --  109.06-125.00  30.00   66
 30  ω     56.00  94.00   0.50    8.45    --  109.06 -99.00 150.00   76
 31  ω     84.00 112.00   0.50    8.45    --  109.06-125.00 -30.00   56
 32  ω     49.00  75.00   0.50    8.45    --  109.06-125.00 -30.00   52
 33  ω     77.00 112.00   0.50    8.45    --  109.06-125.00-150.00   70
 34  ω     87.00 112.00   0.50    8.45    --  109.06-125.00 120.00   50
 35  ω     36.00  78.00   0.50    8.45    --  109.06 -99.00 -60.00   84
 36  ω    149.00 175.00   0.50    8.45    --  109.06  19.00-180.00   52
 37  ω     38.00  74.00   0.50    8.45    --  109.06-125.00-150.00   72
 38  ω     79.00 112.00   0.50    8.45    --  109.06-125.00   0.00   66
 39  ω     55.00 112.00   0.50    8.45    --  109.06-125.00 -90.00  114
 40  ω     43.00 105.00   0.50    8.45    --  109.06 -99.00  90.00  124
 41  ω     38.00  63.00   0.50    8.45    --  109.06 -57.00 120.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1922482000
_diffrn_orient_matrix_UB_12      0.0076217000
_diffrn_orient_matrix_UB_13      0.0309332000
_diffrn_orient_matrix_UB_21      -0.0615710000
_diffrn_orient_matrix_UB_22      -0.1164090000
_diffrn_orient_matrix_UB_23      0.0213199000
_diffrn_orient_matrix_UB_31      0.0362163000
_diffrn_orient_matrix_UB_32      -0.0366887000
_diffrn_orient_matrix_UB_33      -0.0718064000
_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  0.0247
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            24273
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.638
_diffrn_reflns_theta_min         3.508
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.668
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     491
_refine_ls_number_reflns         7566
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0555
_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)+(0.0774P)²+0.4090P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1459
_refine_ls_wR_factor_ref         0.1540
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6152
_reflns_number_total             7566
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc01390a2.cif
_cod_data_source_block           exp_1881_auto
_cod_depositor_comments
'Adding full bibliography for 7131639--7131640.cif.'
_cod_database_code               7131639
_shelx_shelxl_version_number     2018/3
_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   0.906
_shelx_estimated_absorpt_t_min   0.861
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C4(H4), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12),
 C13(H13), C18(H18), C19(H19), C21(H21), C22(H22), N2(H2), C26(H26), C27(H27),
 C29(H29), C30(H30), C33(H33), C34(H34), C35(H35), C36(H36), C41(H41), C42(H42),
  C44(H44), C45(H45)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C46(H46A,H46B,H46C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.267
_oxdiff_exptl_absorpt_empirical_full_min 0.764
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 0.8351(2) 0.72151(11) 0.24943(7) 0.0759(4) Uani 1 1 d . . . . .
O2 O 0.5585(2) 0.36529(11) 0.32642(7) 0.0769(4) Uani 1 1 d . . . . .
O3 O 0.57281(18) 0.18435(12) 0.23344(10) 0.0846(5) Uani 1 1 d . . . . .
N1 N 0.6623(2) 0.56343(11) 0.28062(7) 0.0547(4) Uani 1 1 d . . . . .
H1 H 0.635543 0.525010 0.316203 0.066 Uiso 1 1 calc R U . . .
C1 C 1.1395(4) 0.7552(3) 0.58092(14) 0.1083(10) Uani 1 1 d . . . . .
H1A H 1.232694 0.721774 0.589126 0.162 Uiso 1 1 calc R U . . .
H1B H 1.054532 0.730168 0.613563 0.162 Uiso 1 1 calc R U . . .
H1C H 1.189380 0.830710 0.587258 0.162 Uiso 1 1 calc R U . . .
C2 C 1.0482(3) 0.7282(2) 0.50683(11) 0.0737(6) Uani 1 1 d . . . . .
C3 C 1.0644(4) 0.8019(2) 0.45702(14) 0.1034(9) Uani 1 1 d . . . . .
H3 H 1.134302 0.870992 0.468973 0.124 Uiso 1 1 calc R U . . .
C4 C 0.9810(4) 0.77812(18) 0.38935(13) 0.0926(8) Uani 1 1 d . . . . .
H4 H 0.995281 0.831395 0.356906 0.111 Uiso 1 1 calc R U . . .
C5 C 0.8775(2) 0.67748(14) 0.36884(9) 0.0541(4) Uani 1 1 d . . . . .
C6 C 0.8627(3) 0.60238(18) 0.41894(12) 0.0818(7) Uani 1 1 d . . . . .
H6 H 0.794200 0.532904 0.407156 0.098 Uiso 1 1 calc R U . . .
C7 C 0.9472(4) 0.6279(2) 0.48629(13) 0.0941(8) Uani 1 1 d . . . . .
H7 H 0.934870 0.574854 0.518875 0.113 Uiso 1 1 calc R U . . .
C8 C 0.7916(2) 0.65762(13) 0.29471(9) 0.0526(4) Uani 1 1 d . . . . .
C9 C 0.5678(2) 0.52139(13) 0.21575(8) 0.0475(4) Uani 1 1 d . . . . .
C10 C 0.5459(2) 0.58441(15) 0.15907(9) 0.0563(4) Uani 1 1 d . . . . .
H10 H 0.593987 0.657749 0.163905 0.068 Uiso 1 1 calc R U . . .
C11 C 0.4534(3) 0.53858(17) 0.09603(10) 0.0646(5) Uani 1 1 d . . . . .
H11 H 0.440315 0.581698 0.058674 0.077 Uiso 1 1 calc R U . . .
C12 C 0.3798(3) 0.43039(17) 0.08694(10) 0.0652(5) Uani 1 1 d . . . . .
H12 H 0.318245 0.400505 0.043896 0.078 Uiso 1 1 calc R U . . .
C13 C 0.3987(2) 0.36727(15) 0.14257(9) 0.0580(4) Uani 1 1 d . . . . .
H13 H 0.349034 0.294118 0.136768 0.070 Uiso 1 1 calc R U . . .
C14 C 0.4907(2) 0.41051(13) 0.20755(9) 0.0496(4) Uani 1 1 d . . . . .
C15 C 0.5027(2) 0.33798(14) 0.26461(10) 0.0554(4) Uani 1 1 d . . . . .
C16 C 0.4530(2) 0.21827(14) 0.24762(10) 0.0570(4) Uani 1 1 d . . . . .
C17 C 0.2701(2) 0.15162(13) 0.25090(9) 0.0498(4) Uani 1 1 d . . . . .
C18 C 0.1356(2) 0.19686(14) 0.25887(10) 0.0570(4) Uani 1 1 d . . . . .
H18 H 0.162984 0.269957 0.266231 0.068 Uiso 1 1 calc R U . . .
C19 C -0.0383(3) 0.13493(15) 0.25602(11) 0.0604(4) Uani 1 1 d . . . . .
H19 H -0.127534 0.166646 0.260645 0.072 Uiso 1 1 calc R U . . .
C20 C -0.0818(2) 0.02500(15) 0.24624(10) 0.0579(4) Uani 1 1 d . . . . .
C21 C 0.0546(2) -0.02025(14) 0.24012(10) 0.0562(4) Uani 1 1 d . . . . .
H21 H 0.027944 -0.093592 0.234546 0.067 Uiso 1 1 calc R U . . .
C22 C 0.2281(2) 0.04142(13) 0.24214(9) 0.0523(4) Uani 1 1 d . . . . .
H22 H 0.317641 0.009831 0.237683 0.063 Uiso 1 1 calc R U . . .
C23 C -0.2729(3) -0.0422(2) 0.24182(17) 0.0911(8) Uani 1 1 d . . . . .
H23A H -0.335469 -0.010592 0.271423 0.137 Uiso 1 1 calc R U . . .
H23B H -0.277181 -0.112146 0.257169 0.137 Uiso 1 1 calc R U . . .
H23C H -0.327930 -0.046776 0.194065 0.137 Uiso 1 1 calc R U . . .
O4 O 0.2208(3) 0.47176(14) 0.34533(9) 0.0984(6) Uani 1 1 d . . . . .
O5 O 0.2509(2) 0.77464(11) 0.19228(7) 0.0775(4) Uani 1 1 d . . . . .
O6 O 0.30420(19) 0.75481(13) 0.04119(8) 0.0756(4) Uani 1 1 d . . . . .
N2 N 0.1933(2) 0.60322(13) 0.27286(8) 0.0604(4) Uani 1 1 d . . . . .
H2 H 0.224423 0.671130 0.270022 0.072 Uiso 1 1 calc R U . . .
C24 C 0.6982(5) 0.8715(3) 0.54808(17) 0.1345(13) Uani 1 1 d . . . . .
H24A H 0.626190 0.908719 0.568061 0.202 Uiso 1 1 calc R U . . .
H24B H 0.792996 0.921367 0.528192 0.202 Uiso 1 1 calc R U . . .
H24C H 0.747487 0.834104 0.584126 0.202 Uiso 1 1 calc R U . . .
C25 C 0.5850(4) 0.7933(3) 0.49125(13) 0.0900(7) Uani 1 1 d . . . . .
C26 C 0.5273(4) 0.6886(3) 0.50297(12) 0.0943(8) Uani 1 1 d . . . . .
H26 H 0.558970 0.664481 0.546709 0.113 Uiso 1 1 calc R U . . .
C27 C 0.4223(4) 0.6165(2) 0.45159(12) 0.0874(7) Uani 1 1 d . . . . .
H27 H 0.385296 0.544871 0.461398 0.105 Uiso 1 1 calc R U . . .
C28 C 0.3711(3) 0.64846(18) 0.38612(10) 0.0651(5) Uani 1 1 d . . . . .
C29 C 0.4333(4) 0.7547(2) 0.37387(13) 0.1000(9) Uani 1 1 d . . . . .
H29 H 0.403824 0.779254 0.329998 0.120 Uiso 1 1 calc R U . . .
C30 C 0.5383(5) 0.8252(3) 0.42533(16) 0.1175(11) Uani 1 1 d . . . . .
H30 H 0.579060 0.896583 0.415383 0.141 Uiso 1 1 calc R U . . .
C31 C 0.2555(3) 0.56601(17) 0.33395(10) 0.0647(5) Uani 1 1 d . . . . .
C32 C 0.0865(2) 0.54613(14) 0.21454(9) 0.0535(4) Uani 1 1 d . . . . .
C33 C -0.0118(3) 0.43968(16) 0.21606(11) 0.0633(5) Uani 1 1 d . . . . .
H33 H -0.007852 0.403903 0.257708 0.076 Uiso 1 1 calc R U . . .
C34 C -0.1146(3) 0.38710(16) 0.15654(12) 0.0673(5) Uani 1 1 d . . . . .
H34 H -0.178960 0.316107 0.158715 0.081 Uiso 1 1 calc R U . . .
C35 C -0.1245(3) 0.43690(16) 0.09411(11) 0.0656(5) Uani 1 1 d . . . . .
H35 H -0.193652 0.400217 0.054170 0.079 Uiso 1 1 calc R U . . .
C36 C -0.0298(2) 0.54253(15) 0.09171(10) 0.0592(4) Uani 1 1 d . . . . .
H36 H -0.036353 0.576795 0.049548 0.071 Uiso 1 1 calc R U . . .
C37 C 0.0753(2) 0.59929(14) 0.15066(9) 0.0526(4) Uani 1 1 d . . . . .
C38 C 0.1689(2) 0.71191(15) 0.14403(10) 0.0577(4) Uani 1 1 d . . . . .
C39 C 0.1756(2) 0.75638(15) 0.06987(10) 0.0574(4) Uani 1 1 d . . . . .
C40 C 0.0348(2) 0.80073(14) 0.03915(9) 0.0526(4) Uani 1 1 d . . . . .
C41 C -0.1102(3) 0.79937(16) 0.07403(10) 0.0599(4) Uani 1 1 d . . . . .
H41 H -0.116830 0.772698 0.118846 0.072 Uiso 1 1 calc R U . . .
C42 C -0.2445(3) 0.83739(17) 0.04254(10) 0.0632(5) Uani 1 1 d . . . . .
H42 H -0.342106 0.834788 0.066059 0.076 Uiso 1 1 calc R U . . .
C43 C -0.2362(3) 0.87946(15) -0.02372(10) 0.0574(4) Uani 1 1 d . . . . .
C44 C -0.0901(3) 0.88199(15) -0.05786(9) 0.0580(4) Uani 1 1 d . . . . .
H44 H -0.082156 0.910632 -0.102084 0.070 Uiso 1 1 calc R U . . .
C45 C 0.0436(2) 0.84286(15) -0.02752(9) 0.0562(4) Uani 1 1 d . . . . .
H45 H 0.140075 0.844499 -0.051522 0.067 Uiso 1 1 calc R U . . .
C46 C -0.3838(3) 0.9202(2) -0.05763(12) 0.0762(6) Uani 1 1 d . . . . .
H46A H -0.487199 0.894087 -0.033705 0.114 Uiso 1 1 calc R U . . .
H46B H -0.412219 0.896099 -0.106114 0.114 Uiso 1 1 calc R U . . .
H46C H -0.346406 0.996380 -0.054731 0.114 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 H1 115.9 . . ?
C8 N1 C9 128.23(14) . . ?
C9 N1 H1 115.9 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 121.9(2) . . ?
C3 C2 C7 116.5(2) . . ?
C7 C2 C1 121.6(2) . . ?
C2 C3 H3 118.9 . . ?
C2 C3 C4 122.3(2) . . ?
C4 C3 H3 118.9 . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.2(2) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C6 116.59(19) . . ?
C4 C5 C8 118.25(18) . . ?
C6 C5 C8 125.15(17) . . ?
C5 C6 H6 119.4 . . ?
C5 C6 C7 121.2(2) . . ?
C7 C6 H6 119.4 . . ?
C2 C7 C6 122.2(2) . . ?
C2 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
O1 C8 N1 122.17(16) . . ?
O1 C8 C5 121.98(16) . . ?
N1 C8 C5 115.85(15) . . ?
N1 C9 C14 118.43(14) . . ?
C10 C9 N1 122.75(15) . . ?
C10 C9 C14 118.82(16) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.28(17) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 119.2 . . ?
C10 C11 C12 121.55(18) . . ?
C12 C11 H11 119.2 . . ?
C11 C12 H12 120.6 . . ?
C13 C12 C11 118.86(18) . . ?
C13 C12 H12 120.6 . . ?
C12 C13 H13 119.3 . . ?
C12 C13 C14 121.47(18) . . ?
C14 C13 H13 119.3 . . ?
C9 C14 C15 122.81(15) . . ?
C13 C14 C9 119.01(16) . . ?
C13 C14 C15 118.18(16) . . ?
O2 C15 C14 125.16(17) . . ?
O2 C15 C16 115.31(16) . . ?
C14 C15 C16 119.43(15) . . ?
O3 C16 C15 116.17(16) . . ?
O3 C16 C17 123.93(17) . . ?
C17 C16 C15 119.88(16) . . ?
C18 C17 C16 120.74(16) . . ?
C18 C17 C22 119.12(16) . . ?
C22 C17 C16 120.06(16) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 C17 120.72(17) . . ?
C19 C18 H18 119.6 . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.55(17) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 C23 120.29(19) . . ?
C21 C20 C19 118.45(16) . . ?
C21 C20 C23 121.26(18) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 C20 121.16(16) . . ?
C22 C21 H21 119.4 . . ?
C17 C22 H22 120.0 . . ?
C21 C22 C17 119.97(16) . . ?
C21 C22 H22 120.0 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C31 N2 H2 115.6 . . ?
C31 N2 C32 128.73(17) . . ?
C32 N2 H2 115.6 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C25 C24 H24A 109.5 . . ?
C25 C24 H24B 109.5 . . ?
C25 C24 H24C 109.5 . . ?
C26 C25 C24 121.1(3) . . ?
C26 C25 C30 117.2(3) . . ?
C30 C25 C24 121.7(3) . . ?
C25 C26 H26 119.2 . . ?
C25 C26 C27 121.6(2) . . ?
C27 C26 H26 119.2 . . ?
C26 C27 H27 119.3 . . ?
C28 C27 C26 121.3(3) . . ?
C28 C27 H27 119.3 . . ?
C27 C28 C31 118.1(2) . . ?
C29 C28 C27 116.9(2) . . ?
C29 C28 C31 125.02(19) . . ?
C28 C29 H29 119.5 . . ?
C30 C29 C28 121.0(2) . . ?
C30 C29 H29 119.5 . . ?
C25 C30 H30 119.0 . . ?
C29 C30 C25 121.9(3) . . ?
C29 C30 H30 119.0 . . ?
O4 C31 N2 122.7(2) . . ?
O4 C31 C28 121.74(18) . . ?
N2 C31 C28 115.59(18) . . ?
N2 C32 C33 123.23(16) . . ?
N2 C32 C37 118.29(16) . . ?
C33 C32 C37 118.48(17) . . ?
C32 C33 H33 119.7 . . ?
C34 C33 C32 120.65(18) . . ?
C34 C33 H33 119.7 . . ?
C33 C34 H34 119.2 . . ?
C35 C34 C33 121.56(19) . . ?
C35 C34 H34 119.2 . . ?
C34 C35 H35 120.7 . . ?
C34 C35 C36 118.68(19) . . ?
C36 C35 H35 120.7 . . ?
C35 C36 H36 119.1 . . ?
C35 C36 C37 121.86(18) . . ?
C37 C36 H36 119.1 . . ?
C32 C37 C38 122.80(16) . . ?
C36 C37 C32 118.75(17) . . ?
C36 C37 C38 118.45(16) . . ?
O5 C38 C37 126.06(17) . . ?
O5 C38 C39 115.54(16) . . ?
C37 C38 C39 118.32(16) . . ?
O6 C39 C38 116.06(17) . . ?
O6 C39 C40 124.07(17) . . ?
C40 C39 C38 119.84(16) . . ?
C41 C40 C39 121.58(16) . . ?
C41 C40 C45 118.90(17) . . ?
C45 C40 C39 119.50(16) . . ?
C40 C41 H41 119.8 . . ?
C42 C41 C40 120.30(17) . . ?
C42 C41 H41 119.8 . . ?
C41 C42 H42 119.5 . . ?
C41 C42 C43 120.98(18) . . ?
C43 C42 H42 119.5 . . ?
C42 C43 C46 120.48(18) . . ?
C44 C43 C42 118.47(18) . . ?
C44 C43 C46 121.05(18) . . ?
C43 C44 H44 119.4 . . ?
C45 C44 C43 121.19(17) . . ?
C45 C44 H44 119.4 . . ?
C40 C45 H45 119.9 . . ?
C44 C45 C40 120.14(17) . . ?
C44 C45 H45 119.9 . . ?
C43 C46 H46A 109.5 . . ?
C43 C46 H46B 109.5 . . ?
C43 C46 H46C 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
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 C8 1.219(2) . ?
O2 C15 1.229(2) . ?
O3 C16 1.214(2) . ?
N1 H1 0.8600 . ?
N1 C8 1.363(2) . ?
N1 C9 1.396(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.507(3) . ?
C2 C3 1.354(4) . ?
C2 C7 1.360(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.375(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.369(3) . ?
C5 C6 1.371(3) . ?
C5 C8 1.489(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.375(3) . ?
C7 H7 0.9300 . ?
C9 C10 1.394(2) . ?
C9 C14 1.411(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.375(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.376(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.375(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.396(2) . ?
C14 C15 1.467(2) . ?
C15 C16 1.534(3) . ?
C16 C17 1.467(2) . ?
C17 C18 1.382(3) . ?
C17 C22 1.397(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.375(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.394(3) . ?
C20 C21 1.390(3) . ?
C20 C23 1.507(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.373(2) . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
O4 C31 1.218(3) . ?
O5 C38 1.226(2) . ?
O6 C39 1.216(2) . ?
N2 H2 0.8600 . ?
N2 C31 1.364(2) . ?
N2 C32 1.391(2) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C24 C25 1.510(4) . ?
C25 C26 1.350(4) . ?
C25 C30 1.376(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.381(4) . ?
C27 H27 0.9300 . ?
C27 C28 1.378(3) . ?
C28 C29 1.374(3) . ?
C28 C31 1.490(3) . ?
C29 H29 0.9300 . ?
C29 C30 1.371(4) . ?
C30 H30 0.9300 . ?
C32 C33 1.395(3) . ?
C32 C37 1.418(2) . ?
C33 H33 0.9300 . ?
C33 C34 1.376(3) . ?
C34 H34 0.9300 . ?
C34 C35 1.371(3) . ?
C35 H35 0.9300 . ?
C35 C36 1.380(3) . ?
C36 H36 0.9300 . ?
C36 C37 1.393(3) . ?
C37 C38 1.467(3) . ?
C38 C39 1.539(3) . ?
C39 C40 1.467(3) . ?
C40 C41 1.388(3) . ?
C40 C45 1.395(2) . ?
C41 H41 0.9300 . ?
C41 C42 1.379(3) . ?
C42 H42 0.9300 . ?
C42 C43 1.388(3) . ?
C43 C44 1.384(3) . ?
C43 C46 1.503(3) . ?
C44 H44 0.9300 . ?
C44 C45 1.377(3) . ?
C45 H45 0.9300 . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 0.9600 . ?
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
O2 C15 C16 O3 -87.1(2) . . . . ?
O2 C15 C16 C17 91.4(2) . . . . ?
O3 C16 C17 C18 -172.03(19) . . . . ?
O3 C16 C17 C22 4.5(3) . . . . ?
N1 C9 C10 C11 179.14(17) . . . . ?
N1 C9 C14 C13 -178.83(16) . . . . ?
N1 C9 C14 C15 1.2(3) . . . . ?
C1 C2 C3 C4 -179.7(3) . . . . ?
C1 C2 C7 C6 179.7(3) . . . . ?
C2 C3 C4 C5 -0.4(5) . . . . ?
C3 C2 C7 C6 -1.2(4) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C3 C4 C5 C8 -179.9(3) . . . . ?
C4 C5 C6 C7 0.4(4) . . . . ?
C4 C5 C8 O1 13.4(3) . . . . ?
C4 C5 C8 N1 -167.0(2) . . . . ?
C5 C6 C7 C2 0.4(5) . . . . ?
C6 C5 C8 O1 -166.1(2) . . . . ?
C6 C5 C8 N1 13.6(3) . . . . ?
C7 C2 C3 C4 1.2(5) . . . . ?
C8 N1 C9 C10 -23.5(3) . . . . ?
C8 N1 C9 C14 156.81(18) . . . . ?
C8 C5 C6 C7 179.9(2) . . . . ?
C9 N1 C8 O1 3.8(3) . . . . ?
C9 N1 C8 C5 -175.84(16) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C9 C14 C15 O2 10.0(3) . . . . ?
C9 C14 C15 C16 -166.41(16) . . . . ?
C10 C9 C14 C13 1.5(3) . . . . ?
C10 C9 C14 C15 -178.44(16) . . . . ?
C10 C11 C12 C13 0.4(3) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C12 C13 C14 C9 -0.9(3) . . . . ?
C12 C13 C14 C15 179.09(18) . . . . ?
C13 C14 C15 O2 -170.00(19) . . . . ?
C13 C14 C15 C16 13.6(3) . . . . ?
C14 C9 C10 C11 -1.2(3) . . . . ?
C14 C15 C16 O3 89.6(2) . . . . ?
C14 C15 C16 C17 -91.9(2) . . . . ?
C15 C16 C17 C18 9.7(3) . . . . ?
C15 C16 C17 C22 -173.84(16) . . . . ?
C16 C17 C18 C19 174.49(17) . . . . ?
C16 C17 C22 C21 -175.27(16) . . . . ?
C17 C18 C19 C20 1.1(3) . . . . ?
C18 C17 C22 C21 1.3(3) . . . . ?
C18 C19 C20 C21 0.6(3) . . . . ?
C18 C19 C20 C23 -178.9(2) . . . . ?
C19 C20 C21 C22 -1.3(3) . . . . ?
C20 C21 C22 C17 0.4(3) . . . . ?
C22 C17 C18 C19 -2.1(3) . . . . ?
C23 C20 C21 C22 178.1(2) . . . . ?
O5 C38 C39 O6 84.7(2) . . . . ?
O5 C38 C39 C40 -93.1(2) . . . . ?
O6 C39 C40 C41 179.31(19) . . . . ?
O6 C39 C40 C45 1.1(3) . . . . ?
N2 C32 C33 C34 -179.67(18) . . . . ?
N2 C32 C37 C36 179.29(17) . . . . ?
N2 C32 C37 C38 -1.1(3) . . . . ?
C24 C25 C26 C27 179.4(3) . . . . ?
C24 C25 C30 C29 -179.0(3) . . . . ?
C25 C26 C27 C28 -0.3(4) . . . . ?
C26 C25 C30 C29 1.8(5) . . . . ?
C26 C27 C28 C29 1.7(4) . . . . ?
C26 C27 C28 C31 -179.1(2) . . . . ?
C27 C28 C29 C30 -1.3(5) . . . . ?
C27 C28 C31 O4 -7.4(3) . . . . ?
C27 C28 C31 N2 173.3(2) . . . . ?
C28 C29 C30 C25 -0.4(6) . . . . ?
C29 C28 C31 O4 171.8(3) . . . . ?
C29 C28 C31 N2 -7.6(3) . . . . ?
C30 C25 C26 C27 -1.4(5) . . . . ?
C31 N2 C32 C33 16.5(3) . . . . ?
C31 N2 C32 C37 -164.36(19) . . . . ?
C31 C28 C29 C30 179.5(3) . . . . ?
C32 N2 C31 O4 -0.6(3) . . . . ?
C32 N2 C31 C28 178.78(17) . . . . ?
C32 C33 C34 C35 -0.1(3) . . . . ?
C32 C37 C38 O5 -7.5(3) . . . . ?
C32 C37 C38 C39 169.01(16) . . . . ?
C33 C32 C37 C36 -1.5(3) . . . . ?
C33 C32 C37 C38 178.10(17) . . . . ?
C33 C34 C35 C36 -0.6(3) . . . . ?
C34 C35 C36 C37 0.2(3) . . . . ?
C35 C36 C37 C32 0.8(3) . . . . ?
C35 C36 C37 C38 -178.80(18) . . . . ?
C36 C37 C38 O5 172.1(2) . . . . ?
C36 C37 C38 C39 -11.4(3) . . . . ?
C37 C32 C33 C34 1.2(3) . . . . ?
C37 C38 C39 O6 -92.2(2) . . . . ?
C37 C38 C39 C40 90.0(2) . . . . ?
C38 C39 C40 C41 -3.0(3) . . . . ?
C38 C39 C40 C45 178.71(16) . . . . ?
C39 C40 C41 C42 -177.12(18) . . . . ?
C39 C40 C45 C44 178.14(17) . . . . ?
C40 C41 C42 C43 -1.2(3) . . . . ?
C41 C40 C45 C44 -0.2(3) . . . . ?
C41 C42 C43 C44 0.3(3) . . . . ?
C41 C42 C43 C46 179.72(19) . . . . ?
C42 C43 C44 C45 0.7(3) . . . . ?
C43 C44 C45 C40 -0.7(3) . . . . ?
C45 C40 C41 C42 1.1(3) . . . . ?
C46 C43 C44 C45 -178.72(19) . . . . ?
