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

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

data_exp_268_sq
_database_code_depnum_ccdc_archive 'CCDC 1904275'
loop_
_audit_author_name
_audit_author_address
'Zhiming Duan'
;Shanghai University
China
;
_audit_update_record             
;
2019-03-20 deposited with the CCDC.	2019-04-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C84 H84 N12'
_chemical_formula_weight         1261.63

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'

_space_group_crystal_system      trigonal
_space_group_IT_number           155
_space_group_name_H-M_alt        'R 3 2 :H'
_space_group_name_Hall           'R 3 2"'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z'
'x-y, -y, -z'
'-x, -x+y, -z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+1/3'
'x-y+2/3, -y+1/3, -z+1/3'
'-x+2/3, -x+y+1/3, -z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+2/3'
'x-y+1/3, -y+2/3, -z+2/3'
'-x+1/3, -x+y+2/3, -z+2/3'

_cell_length_a                   16.3765(4)
_cell_length_b                   16.3765(4)
_cell_length_c                   61.2246(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     14220.0(8)
_cell_formula_units_Z            6
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    11229
_cell_measurement_theta_min      4.2440
_cell_measurement_theta_max      64.5300

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    0.884
_exptl_crystal_F_000             4032
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.270
_exptl_absorpt_coefficient_mu    0.409
_shelx_estimated_absorpt_T_min   0.874
_shelx_estimated_absorpt_T_max   0.898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.874
_exptl_absorpt_correction_T_max  0.898
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            47303
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -71
_diffrn_reflns_limit_l_max       76
_diffrn_reflns_theta_min         3.435
_diffrn_reflns_theta_max         76.320
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6410
_reflns_number_gt                4133
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.804
_reflns_Friedel_fraction_max     0.973
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+15.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.0(11)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6410
_refine_ls_number_parameters     294
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1035
_refine_ls_R_factor_gt           0.0806
_refine_ls_wR_factor_ref         0.2339
_refine_ls_wR_factor_gt          0.2201
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_restrained_S_all      0.992
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
N1 N -0.0172(3) 0.2774(3) 0.22634(6) 0.0822(10) Uani 1 1 d . . . . .
H1 H -0.0608 0.2174 0.2261 0.099 Uiso 1 1 calc R U . . .
N2 N -0.0229(3) 0.2794(3) 0.28206(6) 0.0834(10) Uani 1 1 d . . . . .
H2 H 0.0296 0.2771 0.2831 0.100 Uiso 1 1 calc R U . . .
N3 N -0.0236(3) 0.1972(3) 0.18329(6) 0.0861(11) Uani 1 1 d . . . . .
N4 N -0.0119(3) 0.2048(3) 0.32366(7) 0.0914(12) Uani 1 1 d . . . . .
C1 C 0.0345(4) 0.2818(4) 0.18760(8) 0.0885(14) Uani 1 1 d . . . . .
C2 C 0.0404(4) 0.3265(4) 0.20915(8) 0.0852(13) Uani 1 1 d . . . . .
C3 C 0.0961(5) 0.4155(5) 0.21564(10) 0.115(2) Uani 1 1 d . . . . .
C4 C 0.0726(5) 0.4229(4) 0.23786(9) 0.112(2) Uani 1 1 d . . . . .
C5 C 0.0034(4) 0.3357(4) 0.24384(7) 0.0831(13) Uani 1 1 d . . . . .
C6 C -0.0520(4) 0.3061(4) 0.26385(7) 0.0845(13) Uani 1 1 d . . . . .
C7 C -0.1342(4) 0.3036(4) 0.26865(9) 0.0942(15) Uani 1 1 d . . . . .
C8 C -0.1594(4) 0.2706(4) 0.29079(8) 0.0862(14) Uani 1 1 d . . . . .
C9 C -0.0882(4) 0.2564(3) 0.29857(7) 0.0776(12) Uani 1 1 d . . . . .
C10 C -0.0785(4) 0.2231(4) 0.31970(8) 0.0867(14) Uani 1 1 d . . . . .
C11 C -0.0203(4) 0.1669(4) 0.16094(8) 0.0884(14) Uani 1 1 d . . . . .
H11A H 0.0329 0.2189 0.1530 0.106 Uiso 1 1 calc R U . . .
H11B H -0.0794 0.1515 0.1532 0.106 Uiso 1 1 calc R U . . .
C12 C -0.0079(4) 0.0812(4) 0.16124(6) 0.0761(13) Uani 1 1 d . . . . .
C13 C 0.0816(4) 0.0910(4) 0.16146(7) 0.0801(13) Uani 1 1 d . . . . .
C14 C -0.0101(4) 0.1725(4) 0.34593(8) 0.0908(15) Uani 1 1 d . . . . .
H14A H -0.0680 0.1605 0.3538 0.109 Uiso 1 1 calc R U . . .
H14B H 0.0448 0.2224 0.3539 0.109 Uiso 1 1 calc R U . . .
C15 C -0.0040(4) 0.0828(4) 0.34565(7) 0.0863(15) Uani 1 1 d . . . . .
C16 C -0.0882(4) -0.0053(4) 0.34553(8) 0.0828(14) Uani 1 1 d . . . . .
C17 C 0.1635(9) 0.4926(6) 0.20180(15) 0.185(5) Uani 1 1 d . . . . .
H17A H 0.1326 0.4895 0.1877 0.222 Uiso 1 1 calc R U . . .
H17B H 0.1788 0.5531 0.2088 0.222 Uiso 1 1 calc R U . . .
C18 C 0.2443(16) 0.4933(16) 0.1978(2) 0.45(2) Uani 1 1 d . . . . .
H18A H 0.2878 0.5514 0.1900 0.678 Uiso 1 1 calc R U . . .
H18B H 0.2313 0.4387 0.1888 0.678 Uiso 1 1 calc R U . . .
H18C H 0.2728 0.4904 0.2116 0.678 Uiso 1 1 calc R U . . .
C19 C 0.1140(8) 0.5129(7) 0.25215(14) 0.183(5) Uani 1 1 d D . . . .
H19A H 0.1198 0.5663 0.2434 0.219 Uiso 1 1 calc R U . . .
H19B H 0.0711 0.5027 0.2645 0.219 Uiso 1 1 calc R U . . .
C20 C 0.2076(18) 0.536(2) 0.2605(3) 0.381(15) Uani 1 1 d D . . . .
C21 C -0.1913(6) 0.3272(7) 0.25366(13) 0.150(3) Uani 1 1 d . . . . .
H21A H -0.2468 0.3189 0.2620 0.181 Uiso 1 1 calc R U . . .
H21B H -0.1529 0.3952 0.2501 0.181 Uiso 1 1 calc R U . . .
C22 C -0.2228(10) 0.2812(14) 0.23491(15) 0.279(10) Uani 1 1 d . . . . .
H22A H -0.2331 0.2172 0.2365 0.418 Uiso 1 1 calc R U . . .
H22B H -0.1763 0.3145 0.2234 0.418 Uiso 1 1 calc R U . . .
H22C H -0.2824 0.2781 0.2310 0.418 Uiso 1 1 calc R U . . .
C23 C -0.2463(5) 0.2501(5) 0.30263(9) 0.1056(17) Uani 1 1 d . . . . .
H23A H -0.2677 0.2935 0.2974 0.127 Uiso 1 1 calc R U . . .
H23B H -0.2315 0.2627 0.3184 0.127 Uiso 1 1 calc R U . . .
C24 C -0.3261(5) 0.1497(6) 0.29993(13) 0.142(3) Uani 1 1 d . . . . .
H24A H -0.3404 0.1360 0.2844 0.213 Uiso 1 1 calc R U . . .
H24B H -0.3821 0.1419 0.3076 0.213 Uiso 1 1 calc R U . . .
H24C H -0.3073 0.1063 0.3061 0.213 Uiso 1 1 calc R U . . .
C25 C 0.1680(5) 0.1868(4) 0.16307(10) 0.1028(17) Uani 1 1 d . . . . .
C26 C 0.2106(6) 0.2345(6) 0.14054(13) 0.149(3) Uani 1 1 d . . . . .
C27 C -0.1840(5) -0.0121(5) 0.34434(11) 0.118(2) Uani 1 1 d . . . . .
H27A H -0.1764 0.0456 0.3372 0.142 Uiso 1 1 calc R U . . .
H27B H -0.2258 -0.0663 0.3349 0.142 Uiso 1 1 calc R U . . .
C28 C -0.2311(8) -0.0237(9) 0.36594(16) 0.196(4) Uani 1 1 d . . . . .
H28A H -0.2213 -0.0673 0.3750 0.293 Uiso 1 1 calc R U . . .
H28B H -0.2988 -0.0490 0.3637 0.293 Uiso 1 1 calc R U . . .
H28C H -0.2040 0.0377 0.3732 0.293 Uiso 1 1 calc R U . . .


_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
N1 C5 1.360(6) . ?
N1 C2 1.374(6) . ?
N1 H1 0.8800 . ?
N2 C6 1.368(6) . ?
N2 C9 1.380(6) . ?
N2 H2 0.8800 . ?
N3 C1 1.255(7) . ?
N3 C11 1.466(6) . ?
N4 C10 1.291(7) . ?
N4 C14 1.468(6) . ?
C1 C2 1.489(7) . ?
C2 C3 1.335(8) . ?
C3 C4 1.435(8) . ?
C3 C17 1.462(10) . ?
C4 C5 1.356(8) . ?
C4 C19 1.549(10) . ?
C5 C6 1.456(7) . ?
C6 C7 1.359(7) . ?
C7 C8 1.441(7) . ?
C7 C21 1.492(8) . ?
C8 C9 1.384(7) . ?
C8 C23 1.478(7) . ?
C9 C10 1.444(7) . ?
C11 C12 1.515(7) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.393(7) . ?
C12 C13 1.426(7) 2 ?
C13 C12 1.426(7) 3 ?
C13 C25 1.502(8) . ?
C14 C15 1.520(8) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.382(7) 3 ?
C15 C16 1.412(7) . ?
C16 C15 1.382(7) 2 ?
C16 C27 1.518(9) . ?
C17 C18 1.34(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.476(18) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C21 C22 1.328(13) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.512(10) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.566(9) . ?
C27 C28 1.495(11) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C2 109.6(4) . . ?
C5 N1 H1 125.2 . . ?
C2 N1 H1 125.2 . . ?
C6 N2 C9 109.7(4) . . ?
C6 N2 H2 125.1 . . ?
C9 N2 H2 125.1 . . ?
C1 N3 C11 115.7(4) . . ?
C10 N4 C14 115.4(5) . . ?
N3 C1 C2 123.8(5) . . ?
C3 C2 N1 107.7(5) . . ?
C3 C2 C1 130.0(5) . . ?
N1 C2 C1 122.3(5) . . ?
C2 C3 C4 108.0(5) . . ?
C2 C3 C17 125.3(6) . . ?
C4 C3 C17 126.5(7) . . ?
C5 C4 C3 106.5(5) . . ?
C5 C4 C19 126.0(6) . . ?
C3 C4 C19 127.4(6) . . ?
C4 C5 N1 108.1(4) . . ?
C4 C5 C6 129.2(5) . . ?
N1 C5 C6 122.3(5) . . ?
C7 C6 N2 108.2(4) . . ?
C7 C6 C5 129.4(5) . . ?
N2 C6 C5 122.3(5) . . ?
C6 C7 C8 108.0(4) . . ?
C6 C7 C21 126.8(5) . . ?
C8 C7 C21 125.2(5) . . ?
C9 C8 C7 106.2(4) . . ?
C9 C8 C23 126.1(5) . . ?
C7 C8 C23 127.6(5) . . ?
N2 C9 C8 107.8(4) . . ?
N2 C9 C10 122.9(5) . . ?
C8 C9 C10 129.3(5) . . ?
N4 C10 C9 121.4(5) . . ?
N3 C11 C12 110.3(4) . . ?
N3 C11 H11A 109.6 . . ?
C12 C11 H11A 109.6 . . ?
N3 C11 H11B 109.6 . . ?
C12 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C13 C12 C13 121.4(6) . 2 ?
C13 C12 C11 120.9(5) . . ?
C13 C12 C11 117.7(5) 2 . ?
C12 C13 C12 118.6(6) . 3 ?
C12 C13 C25 120.6(5) . . ?
C12 C13 C25 120.8(5) 3 . ?
N4 C14 C15 111.2(4) . . ?
N4 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
N4 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C16 C15 C16 120.9(6) 3 . ?
C16 C15 C14 120.1(6) 3 . ?
C16 C15 C14 119.0(5) . . ?
C15 C16 C15 119.1(6) 2 . ?
C15 C16 C27 119.5(6) 2 . ?
C15 C16 C27 121.3(6) . . ?
C18 C17 C3 115.4(15) . . ?
C18 C17 H17A 108.4 . . ?
C3 C17 H17A 108.4 . . ?
C18 C17 H17B 108.4 . . ?
C3 C17 H17B 108.4 . . ?
H17A C17 H17B 107.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C4 110.0(13) . . ?
C20 C19 H19A 109.7 . . ?
C4 C19 H19A 109.7 . . ?
C20 C19 H19B 109.7 . . ?
C4 C19 H19B 109.7 . . ?
H19A C19 H19B 108.2 . . ?
C22 C21 C7 120.1(9) . . ?
C22 C21 H21A 107.3 . . ?
C7 C21 H21A 107.3 . . ?
C22 C21 H21B 107.3 . . ?
C7 C21 H21B 107.3 . . ?
H21A C21 H21B 106.9 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C8 C23 C24 113.8(5) . . ?
C8 C23 H23A 108.8 . . ?
C24 C23 H23A 108.8 . . ?
C8 C23 H23B 108.8 . . ?
C24 C23 H23B 108.8 . . ?
H23A C23 H23B 107.7 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C13 C25 C26 114.6(5) . . ?
C28 C27 C16 114.6(7) . . ?
C28 C27 H27A 108.6 . . ?
C16 C27 H27A 108.6 . . ?
C28 C27 H27B 108.6 . . ?
C16 C27 H27B 108.6 . . ?
H27A C27 H27B 107.6 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

_refine_diff_density_max         0.301
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.051



####################################################################### 
# 
# 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_exp_199_sq
_database_code_depnum_ccdc_archive 'CCDC 1904276'
loop_
_audit_author_name
_audit_author_address
'Zhiming Duan'
;Shanghai University
China
;
_audit_update_record             
;
2019-03-20 deposited with the CCDC.	2019-04-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C81 H105 N17, 3(H2 O)'
_chemical_formula_sum            'C81 H111 N17 O3'
_chemical_formula_weight         1370.86

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'

_space_group_crystal_system      hexagonal
_space_group_IT_number           176
_space_group_name_H-M_alt        'P 63/m'
_space_group_name_Hall           '-P 6c'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, z+1/2'
'y, -x+y, z+1/2'
'x-y, x, z+1/2'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'x, y, -z-1/2'
'-y, x-y, -z-1/2'
'-x+y, -x, -z-1/2'

_cell_length_a                   17.3339(3)
_cell_length_b                   17.3339(3)
_cell_length_c                   23.8668(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     6210.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    20150
_cell_measurement_theta_min      4.6800
_cell_measurement_theta_max      73.5800

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    0.733
_exptl_crystal_F_000             1480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.361
_shelx_estimated_absorpt_T_min   0.887
_shelx_estimated_absorpt_T_max   0.925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.887
_exptl_absorpt_correction_T_max  0.925
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            68031
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_av_R_equivalents  0.0703
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.478
_diffrn_reflns_theta_max         67.054
_diffrn_reflns_theta_full        67.054
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3807
_reflns_number_gt                3178
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1091P)²+0.4701P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3807
_refine_ls_number_parameters     162
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.1715
_refine_ls_wR_factor_gt          0.1644
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O1W O 0.60505(19) 0.56630(18) 0.7500 0.1086(8) Uani 1 2 d DS T P A 4
H1W H 0.618(2) 0.5485(19) 0.7207(9) 0.163 Uiso 1 1 d D U . B 4
N1 N 0.53330(11) 0.72015(10) 0.7500 0.0532(4) Uani 1 2 d S T P C 4
N2 N 0.56488(8) 0.65266(7) 0.65729(5) 0.0538(3) Uani 1 1 d . . . C 4
H2 H 0.5786 0.6379 0.6895 0.065 Uiso 1 1 calc R U . C 4
N3 N 0.63575(8) 0.53274(8) 0.63688(5) 0.0574(3) Uani 1 1 d . . . C 4
N4 N 0.6667 0.3333 0.63642(8) 0.0523(5) Uani 1 3 d S T P C 4
C1 C 0.47464(16) 0.84120(16) 0.7500 0.0694(6) Uani 1 2 d S T P C 4
H1 H 0.4561 0.8844 0.7500 0.083 Uiso 1 2 calc R U P C 4
C2 C 0.48793(11) 0.81018(11) 0.70027(6) 0.0662(4) Uani 1 1 d . . . C 4
H2A H 0.4772 0.8301 0.6656 0.079 Uiso 1 1 calc R U . C 4
C3 C 0.51750(9) 0.74881(9) 0.70140(5) 0.0540(3) Uani 1 1 d . . . C 4
C4 C 0.53236(9) 0.70960(9) 0.65110(6) 0.0543(3) Uani 1 1 d . . . C 4
C5 C 0.51788(10) 0.71498(10) 0.59420(6) 0.0599(4) Uani 1 1 d . . . C 4
C6 C 0.54324(11) 0.65952(10) 0.56581(6) 0.0635(4) Uani 1 1 d . . . C 4
C7 C 0.57285(10) 0.62227(10) 0.60621(6) 0.0577(4) Uani 1 1 d . . . C 4
C8 C 0.60835(10) 0.56348(10) 0.59827(6) 0.0592(4) Uani 1 1 d . . . C 4
H8 H 0.6115 0.5463 0.5609 0.071 Uiso 1 1 calc R U . C 4
C9 C 0.67307(10) 0.47710(10) 0.61998(6) 0.0611(4) Uani 1 1 d . . . C 4
H9A H 0.7386 0.5111 0.6244 0.073 Uiso 1 1 calc R U . C 4
H9B H 0.6595 0.4609 0.5800 0.073 Uiso 1 1 calc R U . C 4
C10 C 0.63528(9) 0.39376(9) 0.65473(6) 0.0564(4) Uani 1 1 d . . . C 4
H10A H 0.6523 0.4102 0.6944 0.068 Uiso 1 1 calc R U . C 4
H10B H 0.5695 0.3623 0.6524 0.068 Uiso 1 1 calc R U . C 4
C11 C 0.48314(13) 0.76975(12) 0.56673(7) 0.0769(5) Uani 1 1 d . . . C 4
H11A H 0.4330 0.7652 0.5892 0.092 Uiso 1 1 calc R U . C 4
H11B H 0.4598 0.7449 0.5291 0.092 Uiso 1 1 calc R U . C 4
C12 C 0.55308(17) 0.86662(15) 0.56072(9) 0.1027(7) Uani 1 1 d . . . C 4
H12A H 0.5783 0.8911 0.5976 0.154 Uiso 1 1 calc R U . C 4
H12B H 0.5259 0.8996 0.5449 0.154 Uiso 1 1 calc R U . C 4
H12C H 0.6005 0.8721 0.5358 0.154 Uiso 1 1 calc R U . C 4
C13 C 0.53980(15) 0.64506(15) 0.50356(7) 0.0854(6) Uani 1 1 d . . . C 4
H13A H 0.5372 0.5876 0.4963 0.103 Uiso 1 1 calc R U . C 4
H13B H 0.4842 0.6404 0.4888 0.103 Uiso 1 1 calc R U . C 4
C14 C 0.6168(2) 0.7166(2) 0.47220(10) 0.1238(9) Uani 1 1 d . . . C 4
H14A H 0.6157 0.7724 0.4752 0.186 Uiso 1 1 calc R U . C 4
H14B H 0.6128 0.6996 0.4327 0.186 Uiso 1 1 calc R U . C 4
H14C H 0.6725 0.7248 0.4881 0.186 Uiso 1 1 calc R U . C 4


_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
O1W H1W 0.838(17) . ?
N1 C3 1.3429(15) 10_557 ?
N1 C3 1.3430(15) . ?
N2 C7 1.3621(17) . ?
N2 C4 1.3676(17) . ?
N2 H2 0.8800 . ?
N3 C8 1.2696(18) . ?
N3 C9 1.4613(17) . ?
N4 C10 1.4677(14) 3_665 ?
N4 C10 1.4677(14) 2_655 ?
N4 C10 1.4678(14) . ?
C1 C2 1.3693(18) 10_557 ?
C1 C2 1.3693(18) . ?
C1 H1 0.9500 . ?
C2 C3 1.3929(19) . ?
C2 H2A 0.9500 . ?
C3 C4 1.4643(19) . ?
C4 C5 1.393(2) . ?
C5 C6 1.414(2) . ?
C5 C11 1.505(2) . ?
C6 C7 1.393(2) . ?
C6 C13 1.503(2) . ?
C7 C8 1.442(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.5025(19) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.508(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.491(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 C3 119.48(15) 10_557 . ?
C7 N2 C4 109.91(11) . . ?
C7 N2 H2 125.0 . . ?
C4 N2 H2 125.0 . . ?
C8 N3 C9 117.30(12) . . ?
C10 N4 C10 111.52(9) 3_665 2_655 ?
C10 N4 C10 111.52(9) 3_665 . ?
C10 N4 C10 111.53(9) 2_655 . ?
C2 C1 C2 120.19(18) 10_557 . ?
C2 C1 H1 119.9 10_557 . ?
C2 C1 H1 119.9 . . ?
C1 C2 C3 118.78(14) . . ?
C1 C2 H2A 120.6 . . ?
C3 C2 H2A 120.6 . . ?
N1 C3 C2 121.35(13) . . ?
N1 C3 C4 114.87(11) . . ?
C2 C3 C4 123.77(12) . . ?
N2 C4 C5 107.86(12) . . ?
N2 C4 C3 118.56(12) . . ?
C5 C4 C3 133.55(12) . . ?
C4 C5 C6 107.10(12) . . ?
C4 C5 C11 127.54(14) . . ?
C6 C5 C11 125.35(13) . . ?
C7 C6 C5 107.18(13) . . ?
C7 C6 C13 126.86(14) . . ?
C5 C6 C13 125.96(14) . . ?
N2 C7 C6 107.94(12) . . ?
N2 C7 C8 123.54(12) . . ?
C6 C7 C8 128.50(13) . . ?
N3 C8 C7 125.62(13) . . ?
N3 C8 H8 117.2 . . ?
C7 C8 H8 117.2 . . ?
N3 C9 C10 110.98(11) . . ?
N3 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
N3 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
N4 C10 C9 112.50(12) . . ?
N4 C10 H10A 109.1 . . ?
C9 C10 H10A 109.1 . . ?
N4 C10 H10B 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C5 C11 C12 113.04(16) . . ?
C5 C11 H11A 109.0 . . ?
C12 C11 H11A 109.0 . . ?
C5 C11 H11B 109.0 . . ?
C12 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C6 114.39(19) . . ?
C14 C13 H13A 108.7 . . ?
C6 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
C6 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_refine_diff_density_max         0.273
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.033



