#------------------------------------------------------------------------------
#$Date: 2020-10-27 02:09:19 +0200 (Tue, 27 Oct 2020) $
#$Revision: 258605 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/94/1559411.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_1559411
loop_
_publ_author_name
'Wang, Jinhui'
'Jin, Weiyang'
'Zhou, Xiaoxin'
'Li, Jiaqi'
'Xu, Chengdong'
'Ma, Zhongjun'
'Wang, Jianan'
'Qin, Lele'
'Zhou, Biao'
'Ding, Wanjing'
'Gao, Tingting'
'Yao, Hangping'
'Chen, Zhe'
_publ_section_title
;
 Identification, Structure--Activity Relationships of Marine-Derived
 Indolocarbazoles, and a Dual PKCθ/δ Inhibitor with Potent
 Antipancreatic Cancer Efficacy
;
_journal_name_full               'Journal of Medicinal Chemistry'
_journal_paper_doi               10.1021/acs.jmedchem.0c01271
_journal_year                    2020
_chemical_formula_moiety         'C30 H22 N4 O4, C H4 O, C O0.5'
_chemical_formula_sum            'C32 H26 N4 O5.5'
_chemical_formula_weight         554.57
_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     direct
_audit_creation_date             2017-09-12
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                95.819(3)
_cell_angle_beta                 112.387(3)
_cell_angle_gamma                111.273(3)
_cell_formula_units_Z            2
_cell_length_a                   10.6126(3)
_cell_length_b                   11.4102(4)
_cell_length_c                   13.3071(5)
_cell_measurement_reflns_used    19621
_cell_measurement_temperature    170
_cell_measurement_theta_max      66.8652
_cell_measurement_theta_min      3.7368
_cell_volume                     1333.67(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -35.00   33.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.6938   38.0000   90.0000 68

#__ type_ start__ end____ width___ exp.time_
  2 omega  -87.00  -58.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.6938  -44.0000  -31.0000 29

#__ type_ start__ end____ width___ exp.time_
  3 omega  -39.00  -14.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.6938  -44.0000  -31.0000 25

#__ type_ start__ end____ width___ exp.time_
  4 omega  -67.00  -38.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.6938   38.0000   90.0000 29

#__ type_ start__ end____ width___ exp.time_
  5 omega  -50.00  -17.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.6938  -47.0000  111.0000 33

#__ type_ start__ end____ width___ exp.time_
  6 omega  -98.00  -26.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.6938  125.0000 -180.0000 72

#__ type_ start__ end____ width___ exp.time_
  7 omega    8.00   57.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.6938   77.0000  -60.0000 49

#__ type_ start__ end____ width___ exp.time_
  8 omega   10.00   41.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.6938   77.0000  150.0000 31

#__ type_ start__ end____ width___ exp.time_
  9 omega   89.00  118.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.6938   77.0000  150.0000 29

#__ type_ start__ end____ width___ exp.time_
 10 omega   60.00  119.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.6938   77.0000  -60.0000 59

#__ type_ start__ end____ width___ exp.time_
 11 omega   65.00  114.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   76.0000   29.0000 49

#__ type_ start__ end____ width___ exp.time_
 12 omega   14.00   41.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   76.0000   29.0000 27

#__ type_ start__ end____ width___ exp.time_
 13 omega   13.00   39.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   79.0000  107.0000 26

#__ type_ start__ end____ width___ exp.time_
 14 omega   76.00  126.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   79.0000  107.0000 50

#__ type_ start__ end____ width___ exp.time_
 15 omega  -47.00  -15.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -50.0000  -82.0000  -73.0000 32

#__ type_ start__ end____ width___ exp.time_
 16 omega  -44.00  -18.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -54.0000  -84.0000  177.0000 26

#__ type_ start__ end____ width___ exp.time_
 17 omega   23.00   49.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   78.0000  155.0000 26

#__ type_ start__ end____ width___ exp.time_
 18 omega  -57.00  -24.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -79.0000    8.0000 33

#__ type_ start__ end____ width___ exp.time_
 19 omega  -50.00  -24.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -80.0000 -109.0000 26

#__ type_ start__ end____ width___ exp.time_
 20 omega  111.00  136.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   76.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 21 omega   25.00   66.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   76.0000   30.0000 41

#__ type_ start__ end____ width___ exp.time_
 22 omega  110.00  137.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   77.0000  172.0000 27

#__ type_ start__ end____ width___ exp.time_
 23 omega   30.00   56.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   78.0000  109.0000 26

#__ type_ start__ end____ width___ exp.time_
 24 omega   28.00   61.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   77.0000  172.0000 33

#__ type_ start__ end____ width___ exp.time_
 25 omega   35.00   65.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   78.0000  -70.0000 30

#__ type_ start__ end____ width___ exp.time_
 26 omega  -62.00  -37.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -70.0000  -76.0000  171.0000 25

#__ type_ start__ end____ width___ exp.time_
 27 omega  -73.00  -42.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -74.0000  -74.0000  -66.0000 31

#__ type_ start__ end____ width___ exp.time_
 28 omega  -65.00  -40.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -74.0000  -78.0000   70.0000 25

#__ type_ start__ end____ width___ exp.time_
 29 omega  -74.00  -41.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -74.0000  -73.0000    6.0000 33

#__ type_ start__ end____ width___ exp.time_
 30 omega  -73.00  -46.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -78.0000  -74.0000 -102.0000 27

#__ type_ start__ end____ width___ exp.time_
 31 omega  -71.00  -45.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -78.0000  -72.0000  -46.0000 26

#__ type_ start__ end____ width___ exp.time_
 32 omega  -75.00  -50.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -76.0000  -75.0000 25

#__ type_ start__ end____ width___ exp.time_
 33 omega  -78.00  -52.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -73.0000   31.0000 26

#__ type_ start__ end____ width___ exp.time_
 34 omega  -76.00  -49.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -79.0000  170.0000 27

#__ type_ start__ end____ width___ exp.time_
 35 omega  -75.00  -49.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 36 omega  -78.00  -52.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -69.0000   91.0000 26

#__ type_ start__ end____ width___ exp.time_
 37 omega  -76.00  -50.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000 -137.0000 26

#__ type_ start__ end____ width___ exp.time_
 38 omega  -76.00  -50.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -72.0000  126.0000 26

#__ type_ start__ end____ width___ exp.time_
 39 omega  -75.00  -49.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 40 omega  -75.00  -49.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 41 omega  -75.00  -49.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 42 omega   60.00  172.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   90.0000 112

#__ type_ start__ end____ width___ exp.time_
 43 omega   83.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -89.0000   31.0000 26

#__ type_ start__ end____ width___ exp.time_
 44 omega   61.00  171.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000 -150.0000 110

#__ type_ start__ end____ width___ exp.time_
 45 omega   97.00  152.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  150.0000 55

#__ type_ start__ end____ width___ exp.time_
 46 omega   33.00   72.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -89.0000   31.0000 39

#__ type_ start__ end____ width___ exp.time_
 47 omega   83.00  110.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -93.0000  126.0000 27

#__ type_ start__ end____ width___ exp.time_
 48 omega   60.00  157.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  120.0000 97

#__ type_ start__ end____ width___ exp.time_
 49 omega   48.00  129.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -90.0000 -136.0000 81

#__ type_ start__ end____ width___ exp.time_
 50 omega  108.00  146.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   60.0000 38

#__ type_ start__ end____ width___ exp.time_
 51 omega   63.00  103.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   60.0000 40

#__ type_ start__ end____ width___ exp.time_
 52 omega   82.00  117.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -85.0000  -47.0000 35

#__ type_ start__ end____ width___ exp.time_
 53 omega   60.00  171.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000 -180.0000 111

#__ type_ start__ end____ width___ exp.time_
 54 omega   60.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  150.0000 30

#__ type_ start__ end____ width___ exp.time_
 55 omega   99.00  168.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000 -120.0000 69

#__ type_ start__ end____ width___ exp.time_
 56 omega   61.00   94.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000 -120.0000 33

#__ type_ start__ end____ width___ exp.time_
 57 omega   62.00  170.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000    0.0000 108

#__ type_ start__ end____ width___ exp.time_
 58 omega   32.00   70.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -94.0000  -66.0000 38

#__ type_ start__ end____ width___ exp.time_
 59 omega   36.00   76.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000  -60.0000 40

#__ type_ start__ end____ width___ exp.time_
 60 omega  135.00  172.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  -30.0000 37

#__ type_ start__ end____ width___ exp.time_
 61 omega   99.00  132.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  -30.0000 33

#__ type_ start__ end____ width___ exp.time_
 62 omega   61.00   96.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  -30.0000 35

#__ type_ start__ end____ width___ exp.time_
 63 omega   60.00  172.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  -90.0000 112

#__ type_ start__ end____ width___ exp.time_
 64 omega   95.00  170.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   30.0000 75

#__ type_ start__ end____ width___ exp.time_
 65 omega   63.00   92.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   30.0000 29

#__ type_ start__ end____ width___ exp.time_
 66 omega   90.00  172.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  -60.0000 82

#__ type_ start__ end____ width___ exp.time_
 67 omega   42.00  127.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000   60.0000 85

#__ type_ start__ end____ width___ exp.time_
 68 omega   60.00   86.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 69 omega  -99.00  -18.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.6938  125.0000 -120.0000 81

#__ type_ start__ end____ width___ exp.time_
 70 omega  -82.00    9.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.6938   94.0000   66.0000 91

#__ type_ start__ end____ width___ exp.time_
 71 omega  -99.00  -18.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.6938  125.0000   90.0000 81

#__ type_ start__ end____ width___ exp.time_
 72 omega -120.00   -8.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.6938  -77.0000  -60.0000 112

#__ type_ start__ end____ width___ exp.time_
 73 omega   15.00  118.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.6938   38.0000   90.0000 103

#__ type_ start__ end____ width___ exp.time_
 74 omega  -47.00  -15.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -50.0000  -82.0000  -73.0000 32

#__ type_ start__ end____ width___ exp.time_
 75 omega  -48.00  -15.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -50.0000  -81.0000  152.0000 33

#__ type_ start__ end____ width___ exp.time_
 76 omega  -50.00  -24.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -80.0000 -109.0000 26

#__ type_ start__ end____ width___ exp.time_
 77 omega   24.00  138.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   79.0000  144.0000 114

#__ type_ start__ end____ width___ exp.time_
 78 omega   24.00  138.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   79.0000 -170.0000 114

#__ type_ start__ end____ width___ exp.time_
 79 omega   24.00  137.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   78.0000   -9.0000 113

#__ type_ start__ end____ width___ exp.time_
 80 omega   28.00  141.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   78.0000 -111.0000 113

#__ type_ start__ end____ width___ exp.time_
 81 omega   29.00  140.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   76.0000   51.0000 111

#__ type_ start__ end____ width___ exp.time_
 82 omega   29.00  140.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   76.0000  -51.0000 111

#__ type_ start__ end____ width___ exp.time_
 83 omega   28.00  141.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   77.0000  172.0000 113

#__ type_ start__ end____ width___ exp.time_
 84 omega   28.00  141.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   78.0000  109.0000 113

#__ type_ start__ end____ width___ exp.time_
 85 omega   33.00  144.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   76.0000    1.0000 111

#__ type_ start__ end____ width___ exp.time_
 86 omega   32.00  145.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   78.0000  -70.0000 113

#__ type_ start__ end____ width___ exp.time_
 87 omega   66.00  164.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000   90.0000 98

#__ type_ start__ end____ width___ exp.time_
 88 omega   32.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   15.0000 -120.0000 145

#__ type_ start__ end____ width___ exp.time_
 89 omega   73.00  168.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  125.0000    0.0000 95

#__ type_ start__ end____ width___ exp.time_
 90 omega   66.00  168.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000  -60.0000 102

#__ type_ start__ end____ width___ exp.time_
 91 omega   19.00   77.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000  150.0000 58

#__ type_ start__ end____ width___ exp.time_
 92 omega   73.00  168.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  125.0000  120.0000 95

#__ type_ start__ end____ width___ exp.time_
 93 omega   15.00  127.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000   30.0000 112

#__ type_ start__ end____ width___ exp.time_
 94 omega    9.00   83.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -94.0000  -66.0000 74
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0107948000
_diffrn_orient_matrix_UB_12      -0.0045026000
_diffrn_orient_matrix_UB_13      -0.1192181000
_diffrn_orient_matrix_UB_21      0.0351596000
_diffrn_orient_matrix_UB_22      0.1461781000
_diffrn_orient_matrix_UB_23      0.0215802000
_diffrn_orient_matrix_UB_31      0.1705667000
_diffrn_orient_matrix_UB_32      0.0369184000
_diffrn_orient_matrix_UB_33      0.0480764000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0618
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            45204
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        66.977
_diffrn_reflns_theta_max         66.977
_diffrn_reflns_theta_min         3.740
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.788
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61355
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_description       block
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         4692
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0493
_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)+(0.0765P)²+0.7536P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1312
_refine_ls_wR_factor_ref         0.1381
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4151
_reflns_number_total             4692
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jm0c01271_si_004.cif
_cod_data_source_block           170907_a61_34g
_cod_original_cell_volume        1333.67(8)
_cod_original_formula_sum        'C32 H26 N4 O5.50'
_cod_database_code               1559411
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'c h n o'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.743
_shelx_estimated_absorpt_t_min   0.703
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), C11(H11), C12(H12), C13(H13), C14(H14), C17(H17), C18(H18),
 C19(H19), C20(H20), C23(H23), C25(H25), C28(H28), C29(H29)
2.c X=CH2 refined with riding coordinates:
 N4(H4A,H4B)
2.d Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C31(H31A,H31B,H31C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), O5(H5)
;
_olex2_submission_special_instructions 'No special instructions were received'
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 0.22214(17) 0.43062(14) 0.38883(12) 0.0461(4) Uani 1 1 d . . . . .
O2 O 1.05443(13) 0.86342(13) 1.01648(10) 0.0332(3) Uani 1 1 d . . . . .
O3 O 0.24280(14) 0.73072(13) 0.90556(12) 0.0392(4) Uani 1 1 d . . . . .
O4 O 0.33506(17) 0.88320(18) 1.11582(12) 0.0484(4) Uani 1 1 d . . . . .
H4 H 0.251830 0.862263 1.059469 0.073 Uiso 1 1 calc GR . . . .
N1 N 0.30506(19) 0.60615(17) 0.32212(13) 0.0394(4) Uani 1 1 d . . . . .
H1 H 0.240026 0.567064 0.250419 0.047 Uiso 1 1 calc R . . . .
N2 N 0.65744(15) 0.71213(13) 0.81171(11) 0.0221(3) Uani 1 1 d . . . . .
N3 N 0.80089(16) 0.97841(14) 0.75333(12) 0.0255(3) Uani 1 1 d . . . . .
H3 H 0.857690 0.995770 0.826320 0.031 Uiso 1 1 calc R . . . .
N4 N 0.93953(17) 0.74345(15) 0.83632(12) 0.0305(4) Uani 1 1 d . . . . .
H4A H 1.025704 0.747554 0.840104 0.037 Uiso 1 1 calc R . . . .
H4B H 0.855334 0.700429 0.772945 0.037 Uiso 1 1 calc R . . . .
C1 C 0.4177(2) 0.7409(2) 0.36174(15) 0.0349(4) Uani 1 1 d . . . . .
H1A H 0.370236 0.801650 0.346259 0.042 Uiso 1 1 calc R . . . .
H1B H 0.487532 0.754434 0.326913 0.042 Uiso 1 1 calc R . . . .
C2 C 0.3080(2) 0.5456(2) 0.40409(16) 0.0344(4) Uani 1 1 d . . . . .
C3 C 0.4322(2) 0.64292(18) 0.51112(15) 0.0280(4) Uani 1 1 d . . . . .
C4 C 0.4978(2) 0.75752(18) 0.48647(14) 0.0282(4) Uani 1 1 d . . . . .
C5 C 0.6202(2) 0.86821(17) 0.57183(14) 0.0259(4) Uani 1 1 d . . . . .
C6 C 0.67947(18) 0.86046(16) 0.68414(14) 0.0230(4) Uani 1 1 d . . . . .
C7 C 0.61478(18) 0.74287(16) 0.70862(13) 0.0231(4) Uani 1 1 d . . . . .
C8 C 0.48798(19) 0.63332(16) 0.62366(14) 0.0246(4) Uani 1 1 d . . . . .
C9 C 0.44879(19) 0.53271(17) 0.67885(15) 0.0261(4) Uani 1 1 d . . . . .
C10 C 0.55697(18) 0.58377(16) 0.79388(14) 0.0238(4) Uani 1 1 d . . . . .
C11 C 0.5531(2) 0.51286(18) 0.87259(16) 0.0295(4) Uani 1 1 d . . . . .
H11 H 0.627457 0.548710 0.949463 0.035 Uiso 1 1 calc R . . . .
C12 C 0.4366(2) 0.38805(19) 0.83438(17) 0.0360(4) Uani 1 1 d . . . . .
H12 H 0.430870 0.336959 0.885981 0.043 Uiso 1 1 calc R . . . .
C13 C 0.3272(2) 0.33561(19) 0.72126(18) 0.0390(5) Uani 1 1 d . . . . .
H13 H 0.247777 0.249996 0.697768 0.047 Uiso 1 1 calc R . . . .
C14 C 0.3322(2) 0.40543(18) 0.64317(17) 0.0347(4) Uani 1 1 d . . . . .
H14 H 0.257846 0.368111 0.566332 0.042 Uiso 1 1 calc R . . . .
C15 C 0.7086(2) 1.00008(18) 0.57458(15) 0.0284(4) Uani 1 1 d . . . . .
C16 C 0.8180(2) 1.06473(17) 0.68819(15) 0.0278(4) Uani 1 1 d . . . . .
C17 C 0.9238(2) 1.19526(19) 0.72149(18) 0.0363(4) Uani 1 1 d . . . . .
H17 H 0.997380 1.238293 0.798000 0.044 Uiso 1 1 calc R . . . .
C18 C 0.9163(3) 1.2592(2) 0.6375(2) 0.0435(5) Uani 1 1 d . . . . .
H18 H 0.987472 1.347776 0.657392 0.052 Uiso 1 1 calc R . . . .
C19 C 0.8085(3) 1.1983(2) 0.5257(2) 0.0438(5) Uani 1 1 d . . . . .
H19 H 0.806377 1.245952 0.471005 0.053 Uiso 1 1 calc R . . . .
C20 C 0.7036(2) 1.0682(2) 0.49276(18) 0.0372(5) Uani 1 1 d . . . . .
H20 H 0.629968 1.026521 0.416098 0.045 Uiso 1 1 calc R . . . .
C21 C 0.78797(18) 0.79241(16) 0.91542(13) 0.0217(4) Uani 1 1 d . . . . .
C22 C 0.93657(18) 0.80205(16) 0.92602(14) 0.0237(4) Uani 1 1 d . . . . .
C23 C 0.78351(18) 0.85687(16) 1.00326(14) 0.0234(4) Uani 1 1 d . . . . .
H23 H 0.880286 0.907108 1.065954 0.028 Uiso 1 1 calc R . . . .
C24 C 0.65968(19) 0.86501(16) 1.02145(14) 0.0234(4) Uani 1 1 d . . . . .
C25 C 0.50561(19) 0.79498(16) 0.94444(15) 0.0255(4) Uani 1 1 d . . . . .
H25 H 0.476699 0.743704 0.871678 0.031 Uiso 1 1 calc R . . . .
C26 C 0.39582(19) 0.80025(17) 0.97395(15) 0.0273(4) Uani 1 1 d . . . . .
C27 C 0.4371(2) 0.87841(19) 1.08037(16) 0.0311(4) Uani 1 1 d . . . . .
C28 C 0.5886(2) 0.9508(2) 1.15446(15) 0.0333(4) Uani 1 1 d . . . . .
H28 H 0.617343 1.005653 1.225597 0.040 Uiso 1 1 calc R . . . .
C29 C 0.6996(2) 0.94429(18) 1.12619(15) 0.0285(4) Uani 1 1 d . . . . .
H29 H 0.803395 0.994108 1.178408 0.034 Uiso 1 1 calc R . . . .
C30 C 0.1980(3) 0.6378(3) 0.8028(2) 0.0636(8) Uani 1 1 d . . . . .
H30A H 0.233586 0.684116 0.753819 0.095 Uiso 1 1 calc GR . . . .
H30B H 0.087360 0.589436 0.763735 0.095 Uiso 1 1 calc GR . . . .
H30C H 0.242562 0.576346 0.820911 0.095 Uiso 1 1 calc GR . . . .
O5 O 1.0387(2) 0.7949(2) 0.64437(16) 0.0694(5) Uani 1 1 d . . . . .
H5 H 0.963043 0.723257 0.625759 0.104 Uiso 1 1 calc GR . . . .
C31 C 0.9917(3) 0.8824(3) 0.5906(2) 0.0665(8) Uani 1 1 d . . . . .
H31A H 0.953272 0.850056 0.508747 0.100 Uiso 1 1 calc GR . . . .
H31B H 1.077773 0.968968 0.619132 0.100 Uiso 1 1 calc GR . . . .
H31C H 0.911222 0.888781 0.606655 0.100 Uiso 1 1 calc GR . . . .
O6 O 1.000000 0.500000 1.000000 0.194(3) Uani 1 2 d S T P . .
C32 C 0.8842(6) 0.4291(5) 0.9149(3) 0.142(2) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_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
C26 O3 C30 116.39(15) . . ?
C27 O4 H4 109.5 . . ?
C1 N1 H1 122.8 . . ?
C2 N1 H1 122.8 . . ?
C2 N1 C1 114.40(15) . . ?
C7 N2 C21 126.56(14) . . ?
C10 N2 C7 108.07(13) . . ?
C10 N2 C21 125.16(14) . . ?
C6 N3 H3 125.9 . . ?
C6 N3 C16 108.30(14) . . ?
C16 N3 H3 125.9 . . ?
H4A N4 H4B 120.0 . . ?
C22 N4 H4A 120.0 . . ?
C22 N4 H4B 120.0 . . ?
N1 C1 H1A 111.5 . . ?
N1 C1 H1B 111.5 . . ?
N1 C1 C4 101.42(16) . . ?
H1A C1 H1B 109.3 . . ?
C4 C1 H1A 111.5 . . ?
C4 C1 H1B 111.5 . . ?
O1 C2 N1 125.00(17) . . ?
O1 C2 C3 128.74(18) . . ?
N1 C2 C3 106.26(17) . . ?
C4 C3 C2 108.06(16) . . ?
C4 C3 C8 120.78(16) . . ?
C8 C3 C2 131.15(17) . . ?
C3 C4 C1 109.86(16) . . ?
C3 C4 C5 121.14(16) . . ?
C5 C4 C1 129.00(18) . . ?
C4 C5 C6 119.16(16) . . ?
C4 C5 C15 134.52(16) . . ?
C6 C5 C15 106.32(15) . . ?
N3 C6 C5 109.57(15) . . ?
N3 C6 C7 130.83(15) . . ?
C7 C6 C5 119.59(15) . . ?
N2 C7 C6 129.29(15) . . ?
N2 C7 C8 109.47(15) . . ?
C6 C7 C8 121.24(15) . . ?
C3 C8 C9 135.60(16) . . ?
C7 C8 C3 118.01(16) . . ?
C7 C8 C9 106.38(15) . . ?
C10 C9 C8 107.10(15) . . ?
C14 C9 C8 134.48(17) . . ?
C14 C9 C10 118.42(17) . . ?
N2 C10 C9 108.93(15) . . ?
C11 C10 N2 128.37(16) . . ?
C11 C10 C9 122.66(16) . . ?
C10 C11 H11 121.4 . . ?
C12 C11 C10 117.27(17) . . ?
C12 C11 H11 121.4 . . ?
C11 C12 H12 119.4 . . ?
C11 C12 C13 121.26(18) . . ?
C13 C12 H12 119.4 . . ?
C12 C13 H13 119.3 . . ?
C14 C13 C12 121.39(18) . . ?
C14 C13 H13 119.3 . . ?
C9 C14 H14 120.5 . . ?
C13 C14 C9 119.00(18) . . ?
C13 C14 H14 120.5 . . ?
C16 C15 C5 106.53(15) . . ?
C20 C15 C5 133.90(18) . . ?
C20 C15 C16 119.57(18) . . ?
N3 C16 C15 109.24(15) . . ?
N3 C16 C17 128.89(17) . . ?
C17 C16 C15 121.86(17) . . ?
C16 C17 H17 121.6 . . ?
C18 C17 C16 116.8(2) . . ?
C18 C17 H17 121.6 . . ?
C17 C18 H18 118.8 . . ?
C19 C18 C17 122.3(2) . . ?
C19 C18 H18 118.8 . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.68(19) . . ?
C20 C19 H19 119.7 . . ?
C15 C20 H20 120.6 . . ?
C19 C20 C15 118.7(2) . . ?
C19 C20 H20 120.6 . . ?
N2 C21 C22 117.16(14) . . ?
C23 C21 N2 123.80(15) . . ?
C23 C21 C22 119.03(15) . . ?
O2 C22 N4 121.00(15) . . ?
O2 C22 C21 120.98(15) . . ?
N4 C22 C21 118.01(15) . . ?
C21 C23 H23 113.6 . . ?
C21 C23 C24 132.70(15) . . ?
C24 C23 H23 113.6 . . ?
C25 C24 C23 124.82(15) . . ?
C29 C24 C23 116.39(15) . . ?
C29 C24 C25 118.71(16) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 C24 120.34(16) . . ?
C26 C25 H25 119.8 . . ?
O3 C26 C25 124.05(16) . . ?
O3 C26 C27 115.50(16) . . ?
C25 C26 C27 120.44(16) . . ?
O4 C27 C26 123.12(17) . . ?
O4 C27 C28 117.67(17) . . ?
C28 C27 C26 119.17(17) . . ?
C27 C28 H28 119.6 . . ?
C27 C28 C29 120.72(17) . . ?
C29 C28 H28 119.6 . . ?
C24 C29 H29 119.7 . . ?
C28 C29 C24 120.55(17) . . ?
C28 C29 H29 119.7 . . ?
O3 C30 H30A 109.5 . . ?
O3 C30 H30B 109.5 . . ?
O3 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C31 O5 H5 109.5 . . ?
O5 C31 H31A 109.5 . . ?
O5 C31 H31B 109.5 . . ?
O5 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C32 O6 C32 180.0(4) . 2_767 ?
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 C2 1.237(3) . ?
O2 C22 1.245(2) . ?
O3 C26 1.374(2) . ?
O3 C30 1.437(3) . ?
O4 H4 0.8400 . ?
O4 C27 1.351(2) . ?
N1 H1 0.8800 . ?
N1 C1 1.447(3) . ?
N1 C2 1.346(3) . ?
N2 C7 1.396(2) . ?
N2 C10 1.393(2) . ?
N2 C21 1.425(2) . ?
N3 H3 0.8800 . ?
N3 C6 1.381(2) . ?
N3 C16 1.385(2) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
N4 C22 1.325(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C4 1.503(2) . ?
C2 C3 1.479(2) . ?
C3 C4 1.379(3) . ?
C3 C8 1.418(2) . ?
C4 C5 1.403(3) . ?
C5 C6 1.410(2) . ?
C5 C15 1.444(3) . ?
C6 C7 1.403(2) . ?
C7 C8 1.409(2) . ?
C8 C9 1.445(3) . ?
C9 C10 1.413(2) . ?
C9 C14 1.405(3) . ?
C10 C11 1.391(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.383(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.398(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.377(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.412(3) . ?
C15 C20 1.397(3) . ?
C16 C17 1.396(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.388(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.387(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.389(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.490(2) . ?
C21 C23 1.343(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.456(2) . ?
C24 C25 1.404(2) . ?
C24 C29 1.399(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.382(2) . ?
C26 C27 1.407(3) . ?
C27 C28 1.379(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.389(3) . ?
C29 H29 0.9500 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
O5 H5 0.8400 . ?
O5 C31 1.411(4) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
O6 C32 1.216(4) . ?
O6 C32 1.216(4) 2_767 ?
