# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_rbsw71
_database_code_depnum_ccdc_archive 'CCDC 2001285'
loop_
_audit_author_name
_audit_author_address
'Justyna Kalinowska-Tluscik'
;Jagiellonian University
Poland
;
_audit_update_record             
;
2020-05-06 deposited with the CCDC.	2020-08-04 downloaded from the CCDC.
;

_audit_creation_date             2020-03-12T21:03:02-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C56 H60 D12 N8 O15'
_chemical_formula_moiety         'C53 H60 N8 O12, 3(C D4 O)'
_chemical_formula_weight         1109.29

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.20360(10)
_cell_length_b                   14.44280(10)
_cell_length_c                   19.76140(10)
_cell_angle_alpha                79.6540(10)
_cell_angle_beta                 84.5100(10)
_cell_angle_gamma                75.8100(10)
_cell_volume                     2773.37(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    63705
_cell_measurement_theta_min      3.185
_cell_measurement_theta_max      76.353

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_F_000             1168

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.795
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.68282
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.692
_shelx_estimated_absorpt_T_max   0.857

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.0141075
_diffrn_orient_matrix_ub_12      0.0941626
_diffrn_orient_matrix_ub_13      0.0292046
_diffrn_orient_matrix_ub_21      -0.0030906
_diffrn_orient_matrix_ub_22      0.0574111
_diffrn_orient_matrix_ub_23      -0.0737275
_diffrn_orient_matrix_ub_31      -0.1552934
_diffrn_orient_matrix_ub_32      0.0163703
_diffrn_orient_matrix_ub_33      0.0031312
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_number            89827
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.276
_diffrn_reflns_theta_max         77.619
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.961
_reflns_Friedel_coverage         0
_reflns_number_total             11349
_reflns_number_gt                10389
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/1
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0567P)²+1.9476P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.00312(18)
_refine_ls_number_reflns         11349
_refine_ls_number_parameters     777
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.046
_refine_ls_wR_factor_ref         0.127
_refine_ls_wR_factor_gt          0.1194
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.736
_refine_diff_density_min         -0.683
_refine_diff_density_rms         0.054

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'
D D 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O64 O 0.26141(11) 0.82780(7) 0.05898(5) 0.0207(2) Uani 1 1 d . . . . .
O4 O 0.16189(12) 1.12616(8) 0.17873(5) 0.0233(2) Uani 1 1 d . . . . .
O70 O 0.05967(11) 0.89809(8) -0.05536(6) 0.0224(2) Uani 1 1 d . . . . .
O54 O 0.66381(11) 0.70730(8) -0.00917(6) 0.0239(2) Uani 1 1 d . . . . .
O44 O -0.04334(11) 0.67239(8) 0.23487(6) 0.0221(2) Uani 1 1 d . . . . .
O24 O -0.06764(13) 0.93565(8) 0.38366(6) 0.0271(3) Uani 1 1 d . . . . .
O50 O 0.36501(12) 0.61730(9) 0.19899(6) 0.0267(3) Uani 1 1 d . . . . .
O74 O 0.30973(12) 0.63040(9) -0.18569(6) 0.0293(3) Uani 1 1 d . . . . .
N63 N 0.21517(13) 0.95585(9) 0.11610(6) 0.0182(3) Uani 1 1 d . . . . .
N43 N 0.06525(13) 0.76297(9) 0.15293(6) 0.0173(3) Uani 1 1 d . . . . .
N66 N 0.26462(13) 0.93469(9) -0.06695(6) 0.0181(3) Uani 1 1 d . . . . .
O30 O -0.12056(13) 0.68464(9) 0.46853(6) 0.0329(3) Uani 1 1 d . . . . .
O34 O -0.35243(14) 0.41311(9) 0.46832(7) 0.0362(3) Uani 1 1 d . . . . .
N23 N -0.03446(14) 0.81286(9) 0.32200(6) 0.0203(3) Uani 1 1 d . . . . .
N6 N 0.17730(14) 1.11153(9) 0.36312(6) 0.0227(3) Uani 1 1 d . . . . .
N3 N 0.05299(14) 1.04647(9) 0.26737(7) 0.0214(3) Uani 1 1 d . . . . .
N46 N 0.24193(13) 0.60093(9) 0.11415(6) 0.0190(3) Uani 1 1 d . . . . .
N26 N -0.26817(14) 0.75736(10) 0.38650(7) 0.0239(3) Uani 1 1 d . . . . .
O10 O 0.35059(14) 0.98910(10) 0.33925(7) 0.0381(3) Uani 1 1 d . . . . .
O14 O 0.55170(14) 0.81982(9) 0.55702(8) 0.0427(3) Uani 1 1 d . . . . .
C64 C 0.23592(14) 0.91568(10) 0.05885(7) 0.0173(3) Uani 1 1 d . . . . .
C70 C 0.17848(15) 0.88023(10) -0.07823(7) 0.0178(3) Uani 1 1 d . . . . .
C52 C 0.56569(16) 0.66839(11) 0.10531(8) 0.0220(3) Uani 1 1 d . . . . .
H52 H 0.572461 0.664177 0.153428 0.026 Uiso 1 1 calc R U . . .
C51 C 0.45925(15) 0.64389(11) 0.08512(8) 0.0195(3) Uani 1 1 d . . . . .
H51 H 0.451667 0.642369 0.037811 0.023 Uiso 1 1 calc R U . . .
C50 C 0.35378(15) 0.61925(10) 0.13663(8) 0.0194(3) Uani 1 1 d . . . . .
C53 C 0.67059(16) 0.70050(11) 0.06057(8) 0.0211(3) Uani 1 1 d . . . . .
C1 C 0.07489(15) 0.89499(10) 0.21712(7) 0.0173(3) Uani 1 1 d . . . . .
C2 C -0.00712(16) 0.99768(10) 0.22475(7) 0.0190(3) Uani 1 1 d . . . . .
H2A H -0.017731 1.037314 0.178351 0.023 Uiso 1 1 calc R U . . .
H2B H -0.098671 0.993733 0.244797 0.023 Uiso 1 1 calc R U . . .
C71 C 0.23118(16) 0.80045(11) -0.11852(8) 0.0203(3) Uani 1 1 d . . . . .
H71 H 0.324645 0.782955 -0.132089 0.024 Uiso 1 1 calc R U . . .
C22 C 0.09292(16) 0.82807(11) 0.28736(7) 0.0198(3) Uani 1 1 d . . . . .
H22A H 0.152002 0.764638 0.280413 0.024 Uiso 1 1 calc R U . . .
H22B H 0.139085 0.856479 0.317461 0.024 Uiso 1 1 calc R U . . .
C42 C -0.00457(15) 0.85703(10) 0.16990(7) 0.0174(3) Uani 1 1 d . . . . .
H42A H -0.09377 0.852455 0.192993 0.021 Uiso 1 1 calc R U . . .
H42B H -0.020834 0.904079 0.126753 0.021 Uiso 1 1 calc R U . . .
C44 C 0.04428(15) 0.67924(11) 0.18757(7) 0.0183(3) Uani 1 1 d . . . . .
C62 C 0.21759(15) 0.89861(11) 0.18496(7) 0.0182(3) Uani 1 1 d . . . . .
H62A H 0.264171 0.926519 0.215197 0.022 Uiso 1 1 calc R U . . .
H62B H 0.27037 0.831825 0.182491 0.022 Uiso 1 1 calc R U . . .
C4 C 0.13318(17) 1.10655(11) 0.24106(8) 0.0215(3) Uani 1 1 d . . . . .
C7 C 0.09035(17) 1.16708(11) 0.41120(8) 0.0233(3) Uani 1 1 d . . . . .
H7 H 0.132974 1.207131 0.434781 0.028 Uiso 1 1 calc R U . . .
C73 C 0.17624(16) 0.66956(11) -0.16850(8) 0.0227(3) Uani 1 1 d . . . . .
C77 C 0.09762(18) 0.61354(12) -0.18344(9) 0.0298(4) Uani 1 1 d . . . . .
H77 H 0.001951 0.624679 -0.176643 0.036 Uiso 1 1 calc R U . . .
C24 C -0.10510(17) 0.86801(11) 0.36670(8) 0.0223(3) Uani 1 1 d . . . . .
C47 C 0.21830(15) 0.60993(11) 0.04164(8) 0.0207(3) Uani 1 1 d . . . . .
H47 H 0.185857 0.67738 0.016859 0.025 Uiso 1 1 calc R U . . .
C72 C 0.14401(16) 0.75356(11) -0.13539(8) 0.0212(3) Uani 1 1 d . . . . .
H72 H 0.050892 0.778631 -0.124226 0.025 Uiso 1 1 calc R U . . .
C55 C 0.77300(17) 0.74160(12) -0.03924(9) 0.0270(3) Uani 1 1 d . . . . .
H55 H 0.793582 0.753351 -0.087473 0.032 Uiso 1 1 calc R U . . .
C11 C 0.28682(17) 0.99332(11) 0.45778(9) 0.0244(3) Uani 1 1 d . . . . .
H11 H 0.215953 1.01527 0.490064 0.029 Uiso 1 1 calc R U . . .
C45 C 0.13155(16) 0.58746(11) 0.16485(8) 0.0216(3) Uani 1 1 d . . . . .
H45A H 0.170628 0.543378 0.206096 0.026 Uiso 1 1 calc R U . . .
H45B H 0.072459 0.554974 0.145357 0.026 Uiso 1 1 calc R U . . .
C65 C 0.22490(16) 0.98692(10) -0.00901(7) 0.0187(3) Uani 1 1 d . . . . .
H65A H 0.130545 1.025524 -0.013193 0.022 Uiso 1 1 calc R U . . .
H65B H 0.28426 1.031932 -0.009358 0.022 Uiso 1 1 calc R U . . .
C49 C 0.30644(17) 0.53937(12) -0.00063(8) 0.0255(3) Uani 1 1 d . . . . .
H49A H 0.328634 0.563779 -0.04941 0.031 Uiso 1 1 calc R U . . .
H49B H 0.379209 0.48839 0.022611 0.031 Uiso 1 1 calc R U . . .
C48 C 0.16262(18) 0.53379(13) 0.01952(9) 0.0288(4) Uani 1 1 d . . . . .
H48A H 0.096425 0.554713 -0.016895 0.035 Uiso 1 1 calc R U . . .
H48B H 0.146995 0.479334 0.055117 0.035 Uiso 1 1 calc R U . . .
C33 C -0.24214(18) 0.42068(13) 0.49905(9) 0.0286(4) Uani 1 1 d . . . . .
C9 C -0.01972(17) 1.12529(12) 0.45184(8) 0.0258(3) Uani 1 1 d . . . . .
H9A H -0.027378 1.06082 0.444524 0.031 Uiso 1 1 calc R U . . .
H9B H -0.042587 1.138477 0.499547 0.031 Uiso 1 1 calc R U . . .
C31 C -0.25846(18) 0.58884(12) 0.43902(9) 0.0276(3) Uani 1 1 d . . . . .
H31 H -0.329966 0.586762 0.412288 0.033 Uiso 1 1 calc R U . . .
C8 C -0.05515(18) 1.20814(12) 0.39427(9) 0.0295(4) Uani 1 1 d . . . . .
H8A H -0.099842 1.272439 0.406458 0.035 Uiso 1 1 calc R U . . .
H8B H -0.084632 1.194778 0.351432 0.035 Uiso 1 1 calc R U . . .
C10 C 0.27522(17) 1.02990(12) 0.38315(9) 0.0261(3) Uani 1 1 d . . . . .
C57 C 0.78136(17) 0.72980(13) 0.07375(9) 0.0284(4) Uani 1 1 d . . . . .
H57 H 0.809335 0.732052 0.117797 0.034 Uiso 1 1 calc R U . . .
C30 C -0.20979(18) 0.67876(12) 0.43290(8) 0.0262(3) Uani 1 1 d . . . . .
C32 C -0.20035(18) 0.51044(13) 0.48276(9) 0.0288(4) Uani 1 1 d . . . . .
H32 H -0.124167 0.514704 0.505124 0.035 Uiso 1 1 calc R U . . .
C56 C 0.84716(17) 0.75639(12) 0.00895(10) 0.0293(4) Uani 1 1 d . . . . .
H56 H 0.927398 0.779893 0.001197 0.035 Uiso 1 1 calc R U . . .
C5 C 0.18601(19) 1.15526(12) 0.29103(8) 0.0263(3) Uani 1 1 d . . . . .
H5A H 0.281973 1.155135 0.277417 0.032 Uiso 1 1 calc R U . . .
H5B H 0.134843 1.223639 0.286435 0.032 Uiso 1 1 calc R U . . .
C12 C 0.39929(18) 0.92871(12) 0.47868(10) 0.0303(4) Uani 1 1 d . . . . .
H12 H 0.467839 0.911122 0.44418 0.036 Uiso 1 1 calc R U . . .
C13 C 0.42639(18) 0.88322(12) 0.54856(11) 0.0325(4) Uani 1 1 d . . . . .
C25 C -0.24147(18) 0.84961(12) 0.39552(8) 0.0265(3) Uani 1 1 d . . . . .
H25A H -0.249185 0.85278 0.445416 0.032 Uiso 1 1 calc R U . . .
H25B H -0.313239 0.90276 0.373511 0.032 Uiso 1 1 calc R U . . .
C75 C 0.3109(2) 0.54820(13) -0.21108(10) 0.0338(4) Uani 1 1 d . . . . .
H75 H 0.390377 0.505882 -0.22664 0.041 Uiso 1 1 calc R U . . .
C37 C -0.19641(19) 0.33807(13) 0.54424(10) 0.0332(4) Uani 1 1 d . . . . .
H37 H -0.120905 0.324721 0.572028 0.04 Uiso 1 1 calc R U . . .
C17 C 0.3548(2) 0.88483(14) 0.60945(10) 0.0366(4) Uani 1 1 d . . . . .
H17 H 0.266411 0.922761 0.617783 0.044 Uiso 1 1 calc R U . . .
C76 C 0.1852(2) 0.53496(13) -0.21120(10) 0.0350(4) Uani 1 1 d . . . . .
H76 H 0.15987 0.483538 -0.226689 0.042 Uiso 1 1 calc R U . . .
C35 C -0.3745(2) 0.32362(14) 0.49566(11) 0.0388(4) Uani 1 1 d . . . . .
H35 H -0.445374 0.298621 0.483525 0.047 Uiso 1 1 calc R U . . .
C36 C -0.28324(19) 0.27624(13) 0.54164(10) 0.0343(4) Uani 1 1 d . . . . .
H36 H -0.277798 0.213379 0.567494 0.041 Uiso 1 1 calc R U . . .
C16 C 0.4392(2) 0.81765(15) 0.65911(12) 0.0471(5) Uani 1 1 d . . . . .
H16 H 0.417102 0.801795 0.706911 0.056 Uiso 1 1 calc R U . . .
C15 C 0.5550(2) 0.78159(15) 0.62522(13) 0.0473(6) Uani 1 1 d . . . . .
H15 H 0.629547 0.735506 0.645931 0.057 Uiso 1 1 calc R U . . .
C27 C -0.38524(17) 0.76152(12) 0.34933(9) 0.0257(3) Uani 1 1 d . . . . .
H27 H -0.47333 0.768415 0.377091 0.031 Uiso 1 1 calc R U . . .
C29 C -0.37149(18) 0.70572(13) 0.29099(9) 0.0294(4) Uani 1 1 d . . . . .
H29A H -0.448216 0.678223 0.284203 0.035 Uiso 1 1 calc R U . . .
H29B H -0.280805 0.666153 0.279647 0.035 Uiso 1 1 calc R U . . .
C67 C 0.40638(16) 0.91322(12) -0.08788(9) 0.0256(3) Uani 1 1 d . . . . .
H67 H 0.466587 0.858169 -0.059 0.031 Uiso 1 1 calc R U . . .
C69 C 0.4463(2) 0.93218(15) -0.16319(10) 0.0370(4) Uani 1 1 d . . . . .
H69A H 0.528934 0.888998 -0.18044 0.044 Uiso 1 1 calc R U . . .
H69B H 0.372964 0.955383 -0.195843 0.044 Uiso 1 1 calc R U . . .
C28 C -0.39188(19) 0.81384(14) 0.27688(10) 0.0341(4) Uani 1 1 d . . . . .
H28A H -0.313741 0.840736 0.256787 0.041 Uiso 1 1 calc R U . . .
H28B H -0.481114 0.852803 0.261343 0.041 Uiso 1 1 calc R U . . .
C68 C 0.4634(2) 0.99970(16) -0.11712(11) 0.0405(5) Uani 1 1 d . . . . .
H68A H 0.400569 1.064413 -0.121343 0.049 Uiso 1 1 calc R U . . .
H68B H 0.55658 0.99801 -0.105936 0.049 Uiso 1 1 calc R U . . .
O1M O 0.23943(14) 0.35798(10) 0.18110(8) 0.0382(3) Uani 1 1 d . . . . .
O2M O 0.17236(15) 0.39476(10) 0.31502(7) 0.0400(3) Uani 1 1 d . . . . .
O3M O 0.3200(2) 0.51946(16) 0.32395(9) 0.0687(6) Uani 1 1 d . . . . .
C2M C 0.0461(2) 0.43142(15) 0.34960(11) 0.0383(4) Uani 1 1 d . . . . .
C1M C 0.3806(2) 0.34883(16) 0.17358(12) 0.0398(4) Uani 1 1 d . . . . .
C3M C 0.4321(2) 0.49641(19) 0.36478(11) 0.0456(5) Uani 1 1 d . . . . .
H43 H 0.126(2) 0.7628(14) 0.1247(10) 0.022(5) Uiso 1 1 d . . . . .
H3 H 0.043(2) 1.0322(14) 0.3108(11) 0.025(5) Uiso 1 1 d . . . . .
H63 H 0.1924(19) 1.0159(15) 0.1137(10) 0.021(5) Uiso 1 1 d . . . . .
H23 H -0.067(2) 0.7671(15) 0.3109(10) 0.025(5) Uiso 1 1 d . . . . .
D2A D 0.024(3) 0.5071(19) 0.3384(13) 0.053(7) Uiso 1 1 d . . . . .
D2C D -0.029(3) 0.404(2) 0.3323(14) 0.060(8) Uiso 1 1 d . . . . .
D2B D 0.054(2) 0.4080(18) 0.4027(13) 0.049(7) Uiso 1 1 d . . . . .
D1B D 0.432(3) 0.2891(19) 0.2085(14) 0.056(7) Uiso 1 1 d . . . . .
D1C D 0.412(3) 0.341(2) 0.1228(15) 0.063(8) Uiso 1 1 d . . . . .
D1A D 0.407(3) 0.416(2) 0.1807(17) 0.084(10) Uiso 1 1 d . . . . .
D3A D 0.411(2) 0.4522(18) 0.4118(13) 0.047(6) Uiso 1 1 d . . . . .
D1 D 0.219(3) 0.368(2) 0.2340(15) 0.066(8) Uiso 1 1 d . . . . .
D3B D 0.523(3) 0.457(2) 0.3424(15) 0.069(8) Uiso 1 1 d . . . . .
D3 D 0.343(4) 0.556(3) 0.2733(19) 0.094(11) Uiso 1 1 d . . . . .
D3C D 0.451(3) 0.563(2) 0.3761(16) 0.081(10) Uiso 1 1 d . . . . .
D2 D 0.247(3) 0.443(2) 0.3164(15) 0.067(8) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O64 C64 1.2311(18) . ?
O4 C4 1.2368(18) . ?
O70 C70 1.2346(19) . ?
O54 C55 1.3704(19) . ?
O54 C53 1.3711(19) . ?
O44 C44 1.2382(18) . ?
O24 C24 1.2401(19) . ?
O50 C50 1.2432(19) . ?
O74 C75 1.367(2) . ?
O74 C73 1.376(2) . ?
N63 C64 1.3384(19) . ?
N63 C62 1.4588(18) . ?
N63 H63 0.84(2) . ?
N43 C44 1.3333(19) . ?
N43 C42 1.4522(18) . ?
N43 H43 0.79(2) . ?
N66 C70 1.3712(19) . ?
N66 C67 1.439(2) . ?
N66 C65 1.4546(18) . ?
O30 C30 1.231(2) . ?
O34 C33 1.365(2) . ?
O34 C35 1.372(2) . ?
N23 C24 1.336(2) . ?
N23 C22 1.457(2) . ?
N23 H23 0.88(2) . ?
N6 C10 1.369(2) . ?
N6 C7 1.448(2) . ?
N6 C5 1.455(2) . ?
N3 C4 1.341(2) . ?
N3 C2 1.4513(19) . ?
N3 H3 0.85(2) . ?
N46 C50 1.363(2) . ?
N46 C47 1.4533(19) . ?
N46 C45 1.4600(19) . ?
N26 C30 1.372(2) . ?
N26 C27 1.445(2) . ?
N26 C25 1.468(2) . ?
O10 C10 1.235(2) . ?
O14 C15 1.362(3) . ?
O14 C13 1.383(2) . ?
C64 C65 1.5317(19) . ?
C70 C71 1.482(2) . ?
C52 C51 1.336(2) . ?
C52 C53 1.434(2) . ?
C52 H52 0.95 . ?
C51 C50 1.473(2) . ?
C51 H51 0.95 . ?
C53 C57 1.362(2) . ?
C1 C2 1.540(2) . ?
C1 C22 1.5410(19) . ?
C1 C42 1.5411(19) . ?
C1 C62 1.541(2) . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
C71 C72 1.339(2) . ?
C71 H71 0.95 . ?
C22 H22A 0.99 . ?
C22 H22B 0.99 . ?
C42 H42A 0.99 . ?
C42 H42B 0.99 . ?
C44 C45 1.520(2) . ?
C62 H62A 0.99 . ?
C62 H62B 0.99 . ?
C4 C5 1.516(2) . ?
C7 C9 1.502(2) . ?
C7 C8 1.503(2) . ?
C7 H7 1 . ?
C73 C77 1.355(2) . ?
C73 C72 1.434(2) . ?
C77 C76 1.421(2) . ?
C77 H77 0.95 . ?
C24 C25 1.519(2) . ?
C47 C48 1.500(2) . ?
C47 C49 1.503(2) . ?
C47 H47 1 . ?
C72 H72 0.95 . ?
C55 C56 1.347(3) . ?
C55 H55 0.95 . ?
C11 C12 1.336(2) . ?
C11 C10 1.480(2) . ?
C11 H11 0.95 . ?
C45 H45A 0.99 . ?
C45 H45B 0.99 . ?
C65 H65A 0.99 . ?
C65 H65B 0.99 . ?
C49 C48 1.501(2) . ?
C49 H49A 0.99 . ?
C49 H49B 0.99 . ?
C48 H48A 0.99 . ?
C48 H48B 0.99 . ?
C33 C37 1.365(3) . ?
C33 C32 1.436(2) . ?
C9 C8 1.495(2) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C31 C32 1.341(3) . ?
C31 C30 1.482(2) . ?
C31 H31 0.95 . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C57 C56 1.422(2) . ?
C57 H57 0.95 . ?
C32 H32 0.95 . ?
C56 H56 0.95 . ?
C5 H5A 0.99 . ?
C5 H5B 0.99 . ?
C12 C13 1.440(3) . ?
C12 H12 0.95 . ?
C13 C17 1.347(3) . ?
C25 H25A 0.99 . ?
C25 H25B 0.99 . ?
C75 C76 1.343(3) . ?
C75 H75 0.95 . ?
C37 C36 1.413(3) . ?
C37 H37 0.95 . ?
C17 C16 1.434(3) . ?
C17 H17 0.95 . ?
C76 H76 0.95 . ?
C35 C36 1.337(3) . ?
C35 H35 0.95 . ?
C36 H36 0.95 . ?
C16 C15 1.337(4) . ?
C16 H16 0.95 . ?
C15 H15 0.95 . ?
C27 C28 1.494(2) . ?
C27 C29 1.499(2) . ?
C27 H27 1 . ?
C29 C28 1.502(3) . ?
C29 H29A 0.99 . ?
C29 H29B 0.99 . ?
C67 C69 1.499(2) . ?
C67 C68 1.505(3) . ?
C67 H67 1 . ?
C69 C68 1.498(3) . ?
C69 H69A 0.99 . ?
C69 H69B 0.99 . ?
C28 H28A 0.99 . ?
C28 H28B 0.99 . ?
C68 H68A 0.99 . ?
C68 H68B 0.99 . ?
O1M C1M 1.410(2) . ?
O1M D1 1.08(3) . ?
O2M C2M 1.426(2) . ?
O2M D2 1.15(3) . ?
O3M C3M 1.401(3) . ?
O3M D3 1.08(4) . ?
C2M D2A 1.05(3) . ?
C2M D2C 1.05(3) . ?
C2M D2B 1.05(3) . ?
C1M D1B 1.06(3) . ?
C1M D1C 1.04(3) . ?
C1M D1A 1.11(3) . ?
C3M D3A 1.06(2) . ?
C3M D3B 1.06(3) . ?
C3M D3C 1.09(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
C55 O54 C53 106.47(12) . . ?
C75 O74 C73 105.98(13) . . ?
C64 N63 C62 122.53(13) . . ?
C64 N63 H63 120.5(13) . . ?
C62 N63 H63 116.7(13) . . ?
C44 N43 C42 123.91(13) . . ?
C44 N43 H43 119.6(14) . . ?
C42 N43 H43 116.0(14) . . ?
C70 N66 C67 122.92(13) . . ?
C70 N66 C65 115.42(12) . . ?
C67 N66 C65 116.70(12) . . ?
C33 O34 C35 105.97(15) . . ?
C24 N23 C22 122.92(13) . . ?
C24 N23 H23 119.6(13) . . ?
C22 N23 H23 117.4(13) . . ?
C10 N6 C7 123.35(13) . . ?
C10 N6 C5 116.12(14) . . ?
C7 N6 C5 118.77(13) . . ?
C4 N3 C2 122.60(13) . . ?
C4 N3 H3 118.9(13) . . ?
C2 N3 H3 118.3(13) . . ?
C50 N46 C47 123.08(12) . . ?
C50 N46 C45 117.73(13) . . ?
C47 N46 C45 118.39(12) . . ?
C30 N26 C27 123.67(13) . . ?
C30 N26 C25 114.99(14) . . ?
C27 N26 C25 117.40(14) . . ?
C15 O14 C13 106.04(17) . . ?
O64 C64 N63 123.75(13) . . ?
O64 C64 C65 120.79(13) . . ?
N63 C64 C65 115.46(13) . . ?
O70 C70 N66 120.29(13) . . ?
O70 C70 C71 121.19(13) . . ?
N66 C70 C71 118.52(13) . . ?
C51 C52 C53 125.61(15) . . ?
C51 C52 H52 117.2 . . ?
C53 C52 H52 117.2 . . ?
C52 C51 C50 119.62(14) . . ?
C52 C51 H51 120.2 . . ?
C50 C51 H51 120.2 . . ?
O50 C50 N46 120.74(14) . . ?
O50 C50 C51 120.85(14) . . ?
N46 C50 C51 118.38(13) . . ?
C57 C53 O54 109.60(14) . . ?
C57 C53 C52 131.76(15) . . ?
O54 C53 C52 118.62(13) . . ?
C2 C1 C22 111.72(12) . . ?
C2 C1 C42 106.10(11) . . ?
C22 C1 C42 110.87(12) . . ?
C2 C1 C62 110.06(12) . . ?
C22 C1 C62 107.19(12) . . ?
C42 C1 C62 110.95(12) . . ?
N3 C2 C1 114.38(12) . . ?
N3 C2 H2A 108.7 . . ?
C1 C2 H2A 108.7 . . ?
N3 C2 H2B 108.7 . . ?
C1 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
C72 C71 C70 118.47(14) . . ?
C72 C71 H71 120.8 . . ?
C70 C71 H71 120.8 . . ?
N23 C22 C1 113.28(12) . . ?
N23 C22 H22A 108.9 . . ?
C1 C22 H22A 108.9 . . ?
N23 C22 H22B 108.9 . . ?
C1 C22 H22B 108.9 . . ?
H22A C22 H22B 107.7 . . ?
N43 C42 C1 113.08(12) . . ?
N43 C42 H42A 109 . . ?
C1 C42 H42A 109 . . ?
N43 C42 H42B 109 . . ?
C1 C42 H42B 109 . . ?
H42A C42 H42B 107.8 . . ?
O44 C44 N43 124.20(14) . . ?
O44 C44 C45 118.99(13) . . ?
N43 C44 C45 116.77(13) . . ?
N63 C62 C1 112.81(12) . . ?
N63 C62 H62A 109 . . ?
C1 C62 H62A 109 . . ?
N63 C62 H62B 109 . . ?
C1 C62 H62B 109 . . ?
H62A C62 H62B 107.8 . . ?
O4 C4 N3 123.52(14) . . ?
O4 C4 C5 119.12(14) . . ?
N3 C4 C5 117.32(13) . . ?
N6 C7 C9 118.21(13) . . ?
N6 C7 C8 117.37(14) . . ?
C9 C7 C8 59.66(11) . . ?
N6 C7 H7 116.5 . . ?
C9 C7 H7 116.5 . . ?
C8 C7 H7 116.5 . . ?
C77 C73 O74 109.65(14) . . ?
C77 C73 C72 131.41(15) . . ?
O74 C73 C72 118.78(14) . . ?
C73 C77 C76 107.12(16) . . ?
C73 C77 H77 126.4 . . ?
C76 C77 H77 126.4 . . ?
O24 C24 N23 123.45(15) . . ?
O24 C24 C25 118.50(14) . . ?
N23 C24 C25 117.99(14) . . ?
N46 C47 C48 118.14(13) . . ?
N46 C47 C49 119.49(13) . . ?
C48 C47 C49 60.00(11) . . ?
N46 C47 H47 115.9 . . ?
C48 C47 H47 115.9 . . ?
C49 C47 H47 115.9 . . ?
C71 C72 C73 126.95(15) . . ?
C71 C72 H72 116.5 . . ?
C73 C72 H72 116.5 . . ?
C56 C55 O54 110.73(15) . . ?
C56 C55 H55 124.6 . . ?
O54 C55 H55 124.6 . . ?
C12 C11 C10 118.46(16) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
N46 C45 C44 115.65(12) . . ?
N46 C45 H45A 108.4 . . ?
C44 C45 H45A 108.4 . . ?
N46 C45 H45B 108.4 . . ?
C44 C45 H45B 108.4 . . ?
H45A C45 H45B 107.4 . . ?
N66 C65 C64 110.14(12) . . ?
N66 C65 H65A 109.6 . . ?
C64 C65 H65A 109.6 . . ?
N66 C65 H65B 109.6 . . ?
C64 C65 H65B 109.6 . . ?
H65A C65 H65B 108.1 . . ?
C48 C49 C47 59.91(10) . . ?
C48 C49 H49A 117.8 . . ?
C47 C49 H49A 117.8 . . ?
C48 C49 H49B 117.8 . . ?
C47 C49 H49B 117.8 . . ?
H49A C49 H49B 114.9 . . ?
C47 C48 C49 60.09(10) . . ?
C47 C48 H48A 117.8 . . ?
C49 C48 H48A 117.8 . . ?
C47 C48 H48B 117.8 . . ?
C49 C48 H48B 117.8 . . ?
H48A C48 H48B 114.9 . . ?
O34 C33 C37 109.80(15) . . ?
O34 C33 C32 118.02(15) . . ?
C37 C33 C32 132.07(18) . . ?
C8 C9 C7 60.21(11) . . ?
C8 C9 H9A 117.8 . . ?
C7 C9 H9A 117.8 . . ?
C8 C9 H9B 117.8 . . ?
C7 C9 H9B 117.8 . . ?
H9A C9 H9B 114.9 . . ?
C32 C31 C30 119.20(16) . . ?
C32 C31 H31 120.4 . . ?
C30 C31 H31 120.4 . . ?
C9 C8 C7 60.13(11) . . ?
C9 C8 H8A 117.8 . . ?
C7 C8 H8A 117.8 . . ?
C9 C8 H8B 117.8 . . ?
C7 C8 H8B 117.8 . . ?
H8A C8 H8B 114.9 . . ?
O10 C10 N6 119.82(16) . . ?
O10 C10 C11 122.01(16) . . ?
N6 C10 C11 118.17(14) . . ?
C53 C57 C56 106.89(15) . . ?
C53 C57 H57 126.6 . . ?
C56 C57 H57 126.6 . . ?
O30 C30 N26 119.87(15) . . ?
O30 C30 C31 121.87(16) . . ?
N26 C30 C31 118.26(15) . . ?
C31 C32 C33 126.30(17) . . ?
C31 C32 H32 116.9 . . ?
C33 C32 H32 116.9 . . ?
C55 C56 C57 106.30(15) . . ?
C55 C56 H56 126.9 . . ?
C57 C56 H56 126.9 . . ?
N6 C5 C4 115.48(13) . . ?
N6 C5 H5A 108.4 . . ?
C4 C5 H5A 108.4 . . ?
N6 C5 H5B 108.4 . . ?
C4 C5 H5B 108.4 . . ?
H5A C5 H5B 107.5 . . ?
C11 C12 C13 126.16(17) . . ?
C11 C12 H12 116.9 . . ?
C13 C12 H12 116.9 . . ?
C17 C13 O14 110.24(17) . . ?
C17 C13 C12 134.62(17) . . ?
O14 C13 C12 115.09(17) . . ?
N26 C25 C24 116.23(13) . . ?
N26 C25 H25A 108.2 . . ?
C24 C25 H25A 108.2 . . ?
N26 C25 H25B 108.2 . . ?
C24 C25 H25B 108.2 . . ?
H25A C25 H25B 107.4 . . ?
C76 C75 O74 111.25(15) . . ?
C76 C75 H75 124.4 . . ?
O74 C75 H75 124.4 . . ?
C33 C37 C36 106.66(17) . . ?
C33 C37 H37 126.7 . . ?
C36 C37 H37 126.7 . . ?
C13 C17 C16 106.01(19) . . ?
C13 C17 H17 127 . . ?
C16 C17 H17 127 . . ?
C75 C76 C77 106.00(16) . . ?
C75 C76 H76 127 . . ?
C77 C76 H76 127 . . ?
C36 C35 O34 111.06(17) . . ?
C36 C35 H35 124.5 . . ?
O34 C35 H35 124.5 . . ?
C35 C36 C37 106.51(16) . . ?
C35 C36 H36 126.7 . . ?
C37 C36 H36 126.7 . . ?
C15 C16 C17 106.8(2) . . ?
C15 C16 H16 126.6 . . ?
C17 C16 H16 126.6 . . ?
C16 C15 O14 110.87(18) . . ?
C16 C15 H15 124.6 . . ?
O14 C15 H15 124.6 . . ?
N26 C27 C28 117.88(14) . . ?
N26 C27 C29 120.06(14) . . ?
C28 C27 C29 60.25(12) . . ?
N26 C27 H27 115.8 . . ?
C28 C27 H27 115.8 . . ?
C29 C27 H27 115.8 . . ?
C27 C29 C28 59.70(12) . . ?
C27 C29 H29A 117.8 . . ?
C28 C29 H29A 117.8 . . ?
C27 C29 H29B 117.8 . . ?
C28 C29 H29B 117.8 . . ?
H29A C29 H29B 114.9 . . ?
N66 C67 C69 118.40(15) . . ?
N66 C67 C68 115.38(15) . . ?
C69 C67 C68 59.80(12) . . ?
N66 C67 H67 117 . . ?
C69 C67 H67 117 . . ?
C68 C67 H67 117 . . ?
C68 C69 C67 60.29(12) . . ?
C68 C69 H69A 117.7 . . ?
C67 C69 H69A 117.7 . . ?
C68 C69 H69B 117.7 . . ?
C67 C69 H69B 117.7 . . ?
H69A C69 H69B 114.9 . . ?
C27 C28 C29 60.05(11) . . ?
C27 C28 H28A 117.8 . . ?
C29 C28 H28A 117.8 . . ?
C27 C28 H28B 117.8 . . ?
C29 C28 H28B 117.8 . . ?
H28A C28 H28B 114.9 . . ?
C69 C68 C67 59.91(12) . . ?
C69 C68 H68A 117.8 . . ?
C67 C68 H68A 117.8 . . ?
C69 C68 H68B 117.8 . . ?
C67 C68 H68B 117.8 . . ?
H68A C68 H68B 114.9 . . ?
C1M O1M D1 101.1(15) . . ?
C2M O2M D2 110.6(14) . . ?
C3M O3M D3 111.0(19) . . ?
O2M C2M D2A 108.2(14) . . ?
O2M C2M D2C 108.6(15) . . ?
D2A C2M D2C 111(2) . . ?
O2M C2M D2B 109.1(14) . . ?
D2A C2M D2B 110.5(19) . . ?
D2C C2M D2B 109(2) . . ?
O1M C1M D1B 111.0(14) . . ?
O1M C1M D1C 108.1(16) . . ?
D1B C1M D1C 111(2) . . ?
O1M C1M D1A 111.0(17) . . ?
D1B C1M D1A 110(2) . . ?
D1C C1M D1A 105(2) . . ?
O3M C3M D3A 109.2(13) . . ?
O3M C3M D3B 114.7(16) . . ?
D3A C3M D3B 106(2) . . ?
O3M C3M D3C 109.3(17) . . ?
D3A C3M D3C 109(2) . . ?
D3B C3M D3C 108(2) . . ?

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
C62 N63 C64 O64 -1.5(2) . . . . ?
C62 N63 C64 C65 177.98(13) . . . . ?
C67 N66 C70 O70 175.37(14) . . . . ?
C65 N66 C70 O70 21.14(19) . . . . ?
C67 N66 C70 C71 -4.9(2) . . . . ?
C65 N66 C70 C71 -159.17(13) . . . . ?
C53 C52 C51 C50 -175.36(14) . . . . ?
C47 N46 C50 O50 174.81(14) . . . . ?
C45 N46 C50 O50 5.2(2) . . . . ?
C47 N46 C50 C51 -3.6(2) . . . . ?
C45 N46 C50 C51 -173.19(12) . . . . ?
C52 C51 C50 O50 -2.8(2) . . . . ?
C52 C51 C50 N46 175.62(14) . . . . ?
C55 O54 C53 C57 -0.03(17) . . . . ?
C55 O54 C53 C52 178.45(14) . . . . ?
C51 C52 C53 C57 178.04(17) . . . . ?
C51 C52 C53 O54 0.0(2) . . . . ?
C4 N3 C2 C1 94.45(17) . . . . ?
C22 C1 C2 N3 59.70(16) . . . . ?
C42 C1 C2 N3 -179.36(12) . . . . ?
C62 C1 C2 N3 -59.25(16) . . . . ?
O70 C70 C71 C72 6.2(2) . . . . ?
N66 C70 C71 C72 -173.44(14) . . . . ?
C24 N23 C22 C1 -91.93(17) . . . . ?
C2 C1 C22 N23 63.02(16) . . . . ?
C42 C1 C22 N23 -55.10(16) . . . . ?
C62 C1 C22 N23 -176.34(12) . . . . ?
C44 N43 C42 C1 94.34(17) . . . . ?
C2 C1 C42 N43 175.38(12) . . . . ?
C22 C1 C42 N43 -63.13(16) . . . . ?
C62 C1 C42 N43 55.85(16) . . . . ?
C42 N43 C44 O44 5.3(2) . . . . ?
C42 N43 C44 C45 -176.98(13) . . . . ?
C64 N63 C62 C1 -98.88(16) . . . . ?
C2 C1 C62 N63 -61.42(15) . . . . ?
C22 C1 C62 N63 176.89(12) . . . . ?
C42 C1 C62 N63 55.71(16) . . . . ?
C2 N3 C4 O4 0.6(2) . . . . ?
C2 N3 C4 C5 178.17(14) . . . . ?
C10 N6 C7 C9 -73.1(2) . . . . ?
C5 N6 C7 C9 122.61(16) . . . . ?
C10 N6 C7 C8 -141.52(16) . . . . ?
C5 N6 C7 C8 54.2(2) . . . . ?
C75 O74 C73 C77 -0.52(19) . . . . ?
C75 O74 C73 C72 175.43(15) . . . . ?
O74 C73 C77 C76 0.2(2) . . . . ?
C72 C73 C77 C76 -175.06(17) . . . . ?
C22 N23 C24 O24 -1.4(2) . . . . ?
C22 N23 C24 C25 175.64(14) . . . . ?
C50 N46 C47 C48 138.57(15) . . . . ?
C45 N46 C47 C48 -51.92(19) . . . . ?
C50 N46 C47 C49 68.99(19) . . . . ?
C45 N46 C47 C49 -121.50(15) . . . . ?
C70 C71 C72 C73 -174.01(14) . . . . ?
C77 C73 C72 C71 174.95(18) . . . . ?
O74 C73 C72 C71 0.0(2) . . . . ?
C53 O54 C55 C56 -0.02(18) . . . . ?
C50 N46 C45 C44 75.91(17) . . . . ?
C47 N46 C45 C44 -94.17(16) . . . . ?
O44 C44 C45 N46 -173.60(13) . . . . ?
N43 C44 C45 N46 8.5(2) . . . . ?
C70 N66 C65 C64 68.29(16) . . . . ?
C67 N66 C65 C64 -87.60(15) . . . . ?
O64 C64 C65 N66 -7.0(2) . . . . ?
N63 C64 C65 N66 173.46(12) . . . . ?
N46 C47 C49 C48 107.40(16) . . . . ?
N46 C47 C48 C49 -109.62(15) . . . . ?
C35 O34 C33 C37 0.1(2) . . . . ?
C35 O34 C33 C32 -176.51(16) . . . . ?
N6 C7 C9 C8 -106.89(16) . . . . ?
N6 C7 C8 C9 108.29(16) . . . . ?
C7 N6 C10 O10 -176.09(15) . . . . ?
C5 N6 C10 O10 -11.4(2) . . . . ?
C7 N6 C10 C11 4.0(2) . . . . ?
C5 N6 C10 C11 168.62(14) . . . . ?
C12 C11 C10 O10 15.4(2) . . . . ?
C12 C11 C10 N6 -164.63(15) . . . . ?
O54 C53 C57 C56 0.07(19) . . . . ?
C52 C53 C57 C56 -178.15(16) . . . . ?
C27 N26 C30 O30 -171.39(15) . . . . ?
C25 N26 C30 O30 -14.4(2) . . . . ?
C27 N26 C30 C31 7.8(2) . . . . ?
C25 N26 C30 C31 164.84(14) . . . . ?
C32 C31 C30 O30 -2.5(3) . . . . ?
C32 C31 C30 N26 178.28(16) . . . . ?
C30 C31 C32 C33 174.56(16) . . . . ?
O34 C33 C32 C31 -0.9(3) . . . . ?
C37 C33 C32 C31 -176.62(19) . . . . ?
O54 C55 C56 C57 0.06(19) . . . . ?
C53 C57 C56 C55 -0.08(19) . . . . ?
C10 N6 C5 C4 79.00(19) . . . . ?
C7 N6 C5 C4 -115.59(16) . . . . ?
O4 C4 C5 N6 -165.22(15) . . . . ?
N3 C4 C5 N6 17.1(2) . . . . ?
C10 C11 C12 C13 -177.98(15) . . . . ?
C15 O14 C13 C17 0.4(2) . . . . ?
C15 O14 C13 C12 -177.23(15) . . . . ?
C11 C12 C13 C17 4.1(3) . . . . ?
C11 C12 C13 O14 -178.96(16) . . . . ?
C30 N26 C25 C24 79.97(18) . . . . ?
C27 N26 C25 C24 -121.51(16) . . . . ?
O24 C24 C25 N26 -167.09(14) . . . . ?
N23 C24 C25 N26 15.7(2) . . . . ?
C73 O74 C75 C76 0.7(2) . . . . ?
O34 C33 C37 C36 -0.3(2) . . . . ?
C32 C33 C37 C36 175.73(19) . . . . ?
O14 C13 C17 C16 -0.7(2) . . . . ?
C12 C13 C17 C16 176.31(19) . . . . ?
O74 C75 C76 C77 -0.5(2) . . . . ?
C73 C77 C76 C75 0.2(2) . . . . ?
C33 O34 C35 C36 0.1(2) . . . . ?
O34 C35 C36 C37 -0.3(2) . . . . ?
C33 C37 C36 C35 0.3(2) . . . . ?
C13 C17 C16 C15 0.7(2) . . . . ?
C17 C16 C15 O14 -0.5(2) . . . . ?
C13 O14 C15 C16 0.1(2) . . . . ?
C30 N26 C27 C28 -144.12(16) . . . . ?
C25 N26 C27 C28 59.4(2) . . . . ?
C30 N26 C27 C29 -74.1(2) . . . . ?
C25 N26 C27 C29 129.35(16) . . . . ?
N26 C27 C29 C28 -106.95(17) . . . . ?
C70 N66 C67 C69 72.0(2) . . . . ?
C65 N66 C67 C69 -134.03(15) . . . . ?
C70 N66 C67 C68 139.93(15) . . . . ?
C65 N66 C67 C68 -66.14(18) . . . . ?
N66 C67 C69 C68 104.43(18) . . . . ?
N26 C27 C28 C29 110.51(17) . . . . ?
N66 C67 C68 C69 -109.45(17) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_rbsw_1
_database_code_depnum_ccdc_archive 'CCDC 2002330'
loop_
_audit_author_name
_audit_author_address
'Justyna Kalinowska-Tluscik'
;Jagiellonian University
Poland
;
_audit_update_record             
;
2020-05-06 deposited with the CCDC.	2020-08-04 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT315_rbsw_1              
;
PROBLEM: Singly Bonded Carbon Detected (H-atoms Missing).         C4 Check
RESPONSE: The deposited structure is an isocyanide derivative. Thus, it is in the zwitterionic form with the positively charged nitrogen atom N3 and negatively charged C4 carbon atom with a triple bond to N3.
;
# Added during the CSD deposition process: Wednesday 06 May 2020 08:53 PM
# end Validation Reply Form


_audit_creation_date             2020-05-06T21:27:54-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C9 H8 N4'
_chemical_formula_moiety         'C9 H8 N4'
_chemical_formula_weight         172.19

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'P 42/n'
_symmetry_space_group_name_Hall  '-P 4bc'
_symmetry_Int_Tables_number      86
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-y, x+1/2, z+1/2'
'y+1/2, -x, z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'y, -x-1/2, -z-1/2'
'-y-1/2, x, -z-1/2'

_cell_length_a                   8.3584(6)
_cell_length_b                   8.3584(6)
_cell_length_c                   6.7005(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     468.12(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    524
_cell_measurement_theta_min      6.52
_cell_measurement_theta_max      71.775

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#


_exptl_crystal_description       prism
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_F_000             180

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.644
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.25414
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.83
_shelx_estimated_absorpt_T_max   0.882

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_ambient_temperature      130(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.3756
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.1096515
_diffrn_orient_matrix_ub_12      -0.1080792
_diffrn_orient_matrix_ub_13      0.126476
_diffrn_orient_matrix_ub_21      -0.1417184
_diffrn_orient_matrix_ub_22      0.1133044
_diffrn_orient_matrix_ub_23      -0.0404019
_diffrn_orient_matrix_ub_31      -0.0435644
_diffrn_orient_matrix_ub_32      -0.0974703
_diffrn_orient_matrix_ub_33      -0.1873655
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0136
_diffrn_reflns_av_unetI/netI     0.011
_diffrn_reflns_number            671
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       2
_diffrn_reflns_theta_min         8.48
_diffrn_reflns_theta_max         70.847
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.958
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.958
_reflns_Friedel_coverage         0
_reflns_number_total             435
_reflns_number_gt                420
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/1
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1115P)²+0.1664P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.64(7)
_refine_ls_number_reflns         435
_refine_ls_number_parameters     31
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0665
_refine_ls_wR_factor_ref         0.1706
_refine_ls_wR_factor_gt          0.1693
_refine_ls_goodness_of_fit_ref   1.176
_refine_ls_restrained_S_all      1.176
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.112

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
N3 N 0.22787(16) 0.04719(15) 0.0131(2) 0.0170(8) Uani 1 1 d . . . . .
C1 C 0.25 0.25 -0.25 0.0111(9) Uani 1 4 d S T P . .
C2 C 0.13817(16) 0.14657(17) -0.1208(2) 0.0138(7) Uani 1 1 d . . . . .
H2A H 0.066077 0.216855 -0.04295 0.017 Uiso 1 1 calc R U . . .
H2B H 0.071299 0.07847 -0.208264 0.017 Uiso 1 1 calc R U . . .
C4 C 0.3036(2) -0.0300(2) 0.1203(3) 0.0289(8) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
N3 C4 1.154(2) . ?
N3 C2 1.434(2) . ?
C1 C2 1.5398(14) . ?
C1 C2 1.5398(14) 2 ?
C1 C2 1.5398(14) 8_655 ?
C1 C2 1.5398(14) 7_565 ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?

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
C4 N3 C2 178.10(15) . . ?
C2 C1 C2 111.56(11) . 2 ?
C2 C1 C2 108.44(5) . 8_655 ?
C2 C1 C2 108.44(5) 2 8_655 ?
C2 C1 C2 108.44(5) . 7_565 ?
C2 C1 C2 108.44(5) 2 7_565 ?
C2 C1 C2 111.56(11) 8_655 7_565 ?
N3 C2 C1 111.07(10) . . ?
N3 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
N3 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108 . . ?

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
C2 C1 C2 N3 -56.73(9) 2 . . . ?
C2 C1 C2 N3 62.62(7) 8_655 . . . ?
C2 C1 C2 N3 -176.09(12) 7_565 . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_platon_sq
_database_code_depnum_ccdc_archive 'CCDC 2001286'
loop_
_audit_author_name
_audit_author_address
'Justyna Kalinowska-Tluscik'
;Jagiellonian University
Poland
;
_audit_update_record             
;
2020-05-06 deposited with the CCDC.	2020-08-04 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT602_platon_sq           
;
PROBLEM: VERY LARGE Solvent Accessible VOID(S) in Structure        ! Info
RESPONSE: In this structure a higly disordered solvent molecule (ethyl acetate) is present. Additionally, selected atoms of this solvent occupies special positions. The disorder model of this solvent molecule was not possible to be deduced. Due to this, the SQUEEZE procedure was applied. 
;
# Added during the CSD deposition process: Wednesday 06 May 2020 01:28 AM
# end Validation Reply Form


_audit_creation_date             2020-03-15T00:09:03-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C73 H96 F4 N8 O8'
_chemical_formula_weight         1289.57

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'I 41/a'
_symmetry_space_group_name_Hall  '-I 4ad'
_symmetry_Int_Tables_number      88
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y+1/2, z'
'-y+3/4, x+1/4, z+1/4'
'y+1/4, -x+1/4, z+1/4'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1, z+1/2'
'-y+5/4, x+3/4, z+3/4'
'y+3/4, -x+3/4, z+3/4'
'-x, -y, -z'
'x, y-1/2, -z'
'y-3/4, -x-1/4, -z-1/4'
'-y-1/4, x-1/4, -z-1/4'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, y, -z+1/2'
'y-1/4, -x+1/4, -z+1/4'
'-y+1/4, x+1/4, -z+1/4'

_cell_length_a                   15.61510(10)
_cell_length_b                   15.61510(10)
_cell_length_c                   33.2923(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     8117.71(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    62487
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      76.308

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.055
_exptl_crystal_F_000             2760

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.613
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.14e (Rigaku Oxford Diffraction, 2018)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.32117
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.749
_shelx_estimated_absorpt_T_max   0.887

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.0546992
_diffrn_orient_matrix_ub_12      0.0552775
_diffrn_orient_matrix_ub_13      0.0284773
_diffrn_orient_matrix_ub_21      -0.0669718
_diffrn_orient_matrix_ub_22      -0.0722299
_diffrn_orient_matrix_ub_23      0.0025921
_diffrn_orient_matrix_ub_31      0.0475349
_diffrn_orient_matrix_ub_32      -0.0381401
_diffrn_orient_matrix_ub_33      0.0363902
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_number            126535
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         4.889
_diffrn_reflns_theta_max         76.527
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_reflns_Friedel_coverage         0
_reflns_number_total             4260
_reflns_number_gt                4020
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/1
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0684P)²+7.2306P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.00031(5)
_refine_ls_number_reflns         4260
_refine_ls_number_parameters     215
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0636
_refine_ls_wR_factor_ref         0.1703
_refine_ls_wR_factor_gt          0.1691
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.046

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
F19 F 0.22570(9) 0.07826(8) 0.81608(5) 0.0794(4) Uani 1 1 d . . . . .
O4 O 0.21428(9) 0.66457(9) 0.87911(6) 0.0685(5) Uani 1 1 d . . . . .
N3 N 0.07928(11) 0.61173(10) 0.88270(6) 0.0574(5) Uani 1 1 d . . . . .
O7 O 0.09442(10) 0.56967(9) 0.78662(5) 0.0666(4) Uani 1 1 d . . . . .
C1 C 0 0.75 0.875 0.0503(8) Uani 1 4 d S T P . .
N6 N 0.11879(10) 0.47369(10) 0.83521(6) 0.0593(5) Uani 1 1 d . . . . .
C14 C -0.08583(13) 0.40910(14) 0.72517(7) 0.0584(5) Uani 1 1 d . . . . .
H14A H -0.082673 0.347405 0.731862 0.07 Uiso 1 1 calc R U . . .
H14B H -0.136823 0.433273 0.738722 0.07 Uiso 1 1 calc R U . . .
C16 C 0.13272(12) 0.31549(13) 0.84713(7) 0.0565(5) Uani 1 1 d . . . . .
C9 C -0.00560(12) 0.45407(12) 0.74066(6) 0.0533(5) Uani 1 1 d . . . . .
H9 H -0.011746 0.516445 0.734503 0.064 Uiso 1 1 calc R U . . .
C10 C 0.07311(12) 0.42176(13) 0.71832(6) 0.0554(5) Uani 1 1 d . . . . .
H10A H 0.124128 0.453793 0.727594 0.066 Uiso 1 1 calc R U . . .
H10B H 0.082075 0.36048 0.72469 0.066 Uiso 1 1 calc R U . . .
C15 C 0.09365(14) 0.40045(13) 0.85956(7) 0.0598(5) Uani 1 1 d . . . . .
H15A H 0.030516 0.395053 0.858551 0.072 Uiso 1 1 calc R U . . .
H15B H 0.109749 0.412046 0.887799 0.072 Uiso 1 1 calc R U . . .
C19 C 0.19593(13) 0.15718(13) 0.82678(8) 0.0649(6) Uani 1 1 d . . . . .
C21 C 0.11323(13) 0.24353(14) 0.87002(8) 0.0619(5) Uani 1 1 d . . . . .
H21 H 0.078018 0.249522 0.893119 0.074 Uiso 1 1 calc R U . . .
C17 C 0.18595(13) 0.30646(13) 0.81429(7) 0.0604(5) Uani 1 1 d . . . . .
H17 H 0.200222 0.355214 0.798587 0.073 Uiso 1 1 calc R U . . .
C20 C 0.14416(13) 0.16335(14) 0.85978(8) 0.0642(6) Uani 1 1 d . . . . .
H20 H 0.129878 0.114185 0.875191 0.077 Uiso 1 1 calc R U . . .
C2 C 0.04121(13) 0.68403(11) 0.90330(7) 0.0541(5) Uani 1 1 d . . . . .
H2A H 0.08597 0.712939 0.919416 0.065 Uiso 1 1 calc R U . . .
H2B H -0.002989 0.662612 0.922105 0.065 Uiso 1 1 calc R U . . .
C7 C 0.07575(13) 0.50097(12) 0.80236(7) 0.0569(5) Uani 1 1 d . . . . .
C8 C 0.00400(12) 0.44533(13) 0.78593(7) 0.0552(5) Uani 1 1 d . . . . .
H8A H -0.050526 0.461693 0.79902 0.066 Uiso 1 1 calc R U . . .
H8B H 0.015786 0.384713 0.79266 0.066 Uiso 1 1 calc R U . . .
C18 C 0.21899(14) 0.22638(14) 0.80394(8) 0.0642(6) Uani 1 1 d . . . . .
H18 H 0.256468 0.220055 0.781659 0.077 Uiso 1 1 calc R U . . .
C11 C 0.06397(14) 0.43224(17) 0.67331(7) 0.0669(6) Uani 1 1 d . . . . .
H11A H 0.114707 0.407271 0.659867 0.08 Uiso 1 1 calc R U . . .
H11B H 0.062004 0.494012 0.666669 0.08 Uiso 1 1 calc R U . . .
C4 C 0.16100(13) 0.60802(13) 0.87170(8) 0.0615(6) Uani 1 1 d . . . . .
C5 C 0.18888(13) 0.52735(14) 0.84962(9) 0.0683(6) Uani 1 1 d . . . . .
H5A H 0.224593 0.54425 0.826359 0.082 Uiso 1 1 calc R U . . .
H5B H 0.225213 0.492839 0.867834 0.082 Uiso 1 1 calc R U . . .
C13 C -0.09540(15) 0.41941(18) 0.68015(8) 0.0715(6) Uani 1 1 d . . . . .
H13A H -0.105886 0.480478 0.673845 0.086 Uiso 1 1 calc R U . . .
H13B H -0.145753 0.38624 0.670962 0.086 Uiso 1 1 calc R U . . .
C12 C -0.01631(15) 0.38911(19) 0.65748(7) 0.0730(6) Uani 1 1 d . . . . .
H12A H -0.010645 0.326262 0.660372 0.088 Uiso 1 1 calc R U . . .
H12B H -0.022969 0.402252 0.628561 0.088 Uiso 1 1 calc R U . . .
H3 H 0.0474(16) 0.5713(16) 0.8758(7) 0.064(7) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
F19 C19 1.364(2) . ?
O4 C4 1.238(2) . ?
N3 C4 1.329(3) . ?
N3 C2 1.449(2) . ?
N3 H3 0.84(3) . ?
O7 C7 1.229(3) . ?
C1 C2 1.5372(19) . ?
C1 C2 1.537(2) 11_567 ?
C1 C2 1.5373(19) 2_565 ?
C1 C2 1.537(2) 12_667 ?
N6 C7 1.353(3) . ?
N6 C15 1.456(3) . ?
N6 C5 1.460(3) . ?
C14 C13 1.515(3) . ?
C14 C9 1.526(3) . ?
C14 H14A 0.99 . ?
C14 H14B 0.99 . ?
C16 C17 1.380(3) . ?
C16 C21 1.392(3) . ?
C16 C15 1.518(3) . ?
C9 C8 1.521(3) . ?
C9 C10 1.523(3) . ?
C9 H9 1 . ?
C10 C11 1.514(3) . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C15 H15A 0.99 . ?
C15 H15B 0.99 . ?
C19 C20 1.367(3) . ?
C19 C18 1.369(3) . ?
C21 C20 1.385(3) . ?
C21 H21 0.95 . ?
C17 C18 1.396(3) . ?
C17 H17 0.95 . ?
C20 H20 0.95 . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
C7 C8 1.520(3) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C18 H18 0.95 . ?
C11 C12 1.518(3) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C4 C5 1.522(3) . ?
C5 H5A 0.99 . ?
C5 H5B 0.99 . ?
C13 C12 1.523(3) . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?

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
C4 N3 C2 123.96(17) . . ?
C4 N3 H3 117.6(17) . . ?
C2 N3 H3 118.3(17) . . ?
C2 C1 C2 112.07(8) . 11_567 ?
C2 C1 C2 104.39(15) . 2_565 ?
C2 C1 C2 112.07(8) 11_567 2_565 ?
C2 C1 C2 112.07(8) . 12_667 ?
C2 C1 C2 104.39(15) 11_567 12_667 ?
C2 C1 C2 112.07(8) 2_565 12_667 ?
C7 N6 C15 124.31(17) . . ?
C7 N6 C5 117.22(19) . . ?
C15 N6 C5 118.1(2) . . ?
C13 C14 C9 111.50(18) . . ?
C13 C14 H14A 109.3 . . ?
C9 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
C9 C14 H14B 109.3 . . ?
H14A C14 H14B 108 . . ?
C17 C16 C21 118.88(19) . . ?
C17 C16 C15 123.2(2) . . ?
C21 C16 C15 117.9(2) . . ?
C8 C9 C10 112.01(16) . . ?
C8 C9 C14 112.00(17) . . ?
C10 C9 C14 110.19(17) . . ?
C8 C9 H9 107.5 . . ?
C10 C9 H9 107.5 . . ?
C14 C9 H9 107.5 . . ?
C11 C10 C9 111.81(17) . . ?
C11 C10 H10A 109.3 . . ?
C9 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
N6 C15 C16 115.25(19) . . ?
N6 C15 H15A 108.5 . . ?
C16 C15 H15A 108.5 . . ?
N6 C15 H15B 108.5 . . ?
C16 C15 H15B 108.5 . . ?
H15A C15 H15B 107.5 . . ?
F19 C19 C20 118.3(2) . . ?
F19 C19 C18 118.6(2) . . ?
C20 C19 C18 123.1(2) . . ?
C20 C21 C16 121.3(2) . . ?
C20 C21 H21 119.4 . . ?
C16 C21 H21 119.4 . . ?
C16 C17 C18 120.6(2) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C19 C20 C21 117.9(2) . . ?
C19 C20 H20 121.1 . . ?
C21 C20 H20 121.1 . . ?
N3 C2 C1 113.82(16) . . ?
N3 C2 H2A 108.8 . . ?
C1 C2 H2A 108.8 . . ?
N3 C2 H2B 108.8 . . ?
C1 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
O7 C7 N6 120.13(19) . . ?
O7 C7 C8 121.4(2) . . ?
N6 C7 C8 118.50(18) . . ?
C7 C8 C9 112.21(17) . . ?
C7 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C19 C18 C17 118.2(2) . . ?
C19 C18 H18 120.9 . . ?
C17 C18 H18 120.9 . . ?
C10 C11 C12 111.93(19) . . ?
C10 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
C10 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
O4 C4 N3 124.01(19) . . ?
O4 C4 C5 119.62(19) . . ?
N3 C4 C5 116.35(17) . . ?
N6 C5 C4 114.79(16) . . ?
N6 C5 H5A 108.6 . . ?
C4 C5 H5A 108.6 . . ?
N6 C5 H5B 108.6 . . ?
C4 C5 H5B 108.6 . . ?
H5A C5 H5B 107.5 . . ?
C14 C13 C12 112.17(19) . . ?
C14 C13 H13A 109.2 . . ?
C12 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
C12 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C11 C12 C13 111.1(2) . . ?
C11 C12 H12A 109.4 . . ?
C13 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108 . . ?

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
C13 C14 C9 C8 179.12(18) . . . . ?
C13 C14 C9 C10 -55.5(2) . . . . ?
C8 C9 C10 C11 -178.85(18) . . . . ?
C14 C9 C10 C11 55.8(2) . . . . ?
C7 N6 C15 C16 91.1(2) . . . . ?
C5 N6 C15 C16 -96.4(2) . . . . ?
C17 C16 C15 N6 -2.3(3) . . . . ?
C21 C16 C15 N6 178.03(18) . . . . ?
C17 C16 C21 C20 -1.8(3) . . . . ?
C15 C16 C21 C20 177.85(19) . . . . ?
C21 C16 C17 C18 0.7(3) . . . . ?
C15 C16 C17 C18 -179.0(2) . . . . ?
F19 C19 C20 C21 -179.02(19) . . . . ?
C18 C19 C20 C21 0.8(3) . . . . ?
C16 C21 C20 C19 1.2(3) . . . . ?
C4 N3 C2 C1 92.8(2) . . . . ?
C2 C1 C2 N3 54.4(2) 11_567 . . . ?
C2 C1 C2 N3 175.9(2) 2_565 . . . ?
C2 C1 C2 N3 -62.6(2) 12_667 . . . ?
C15 N6 C7 O7 170.33(18) . . . . ?
C5 N6 C7 O7 -2.2(3) . . . . ?
C15 N6 C7 C8 -9.1(3) . . . . ?
C5 N6 C7 C8 178.35(17) . . . . ?
O7 C7 C8 C9 31.5(3) . . . . ?
N6 C7 C8 C9 -149.13(18) . . . . ?
C10 C9 C8 C7 64.3(2) . . . . ?
C14 C9 C8 C7 -171.26(16) . . . . ?
F19 C19 C18 C17 177.88(19) . . . . ?
C20 C19 C18 C17 -1.9(3) . . . . ?
C16 C17 C18 C19 1.1(3) . . . . ?
C9 C10 C11 C12 -55.4(3) . . . . ?
C2 N3 C4 O4 2.7(4) . . . . ?
C2 N3 C4 C5 -178.9(2) . . . . ?
C7 N6 C5 C4 75.4(3) . . . . ?
C15 N6 C5 C4 -97.7(2) . . . . ?
O4 C4 C5 N6 -167.9(2) . . . . ?
N3 C4 C5 N6 13.6(3) . . . . ?
C9 C14 C13 C12 55.0(3) . . . . ?
C10 C11 C12 C13 53.5(3) . . . . ?
C14 C13 C12 C11 -53.5(3) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_refine_special_details          SQUEEZE
