# 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_mj19077_0m
_database_code_depnum_ccdc_archive 'CCDC 1894496'
loop_
_audit_author_name
_audit_author_address
'Feng Zhou'
;East China Normal University
China
;
_audit_update_record             
;
2019-01-30 deposited with the CCDC.	2019-11-12 downloaded from the CCDC.
;
_audit_creation_date             2019-01-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'F6 Sb, C26 H26 Ag N6'
_chemical_formula_sum            'C26 H26 Ag F6 N6 Sb'
_chemical_formula_weight         766.15
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0148 0.0070 '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'
Ag Ag 0.0782 3.3823 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0599 0.0411 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb 0.0887 4.4825 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   14.7369(6)
_cell_length_b                   31.5086(13)
_cell_length_c                   5.9773(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2775.49(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2080
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      43.34
_cell_measurement_theta_min      4.89
_shelx_estimated_absorpt_T_max   0.911
_shelx_estimated_absorpt_T_min   0.764
_exptl_absorpt_coefficient_mu    9.462
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1537 before and 0.0851 after correction. The Ratio of minimum to maximum transmission is 0.5511. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.833
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1534
_diffrn_reflns_av_unetI/netI     0.1249
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            22100
_diffrn_reflns_point_group_measured_fraction_full 0.851
_diffrn_reflns_point_group_measured_fraction_max 0.841
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.953
_diffrn_reflns_theta_min         2.880
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.536
_reflns_Friedel_fraction_full    0.670
_reflns_Friedel_fraction_max     0.654
_reflns_number_gt                2208
_reflns_number_total             4443
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.912
_refine_diff_density_min         -1.434
_refine_diff_density_rms         0.152
_refine_ls_abs_structure_details 
;
 Flack x determined using 562 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         4443
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1557
_refine_ls_R_factor_gt           0.0639
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0812P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1822
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Riding coordinates:
 N3(H3)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N4(H4), N5(H5A), N6(H6A), C3(H3A), C4(H4A), C5(H5), C6(H6),
 C7(H7), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sb1 Sb -1.26843(10) -0.37425(5) 0.8989(2) 0.0400(5) Uani 1 1 d . . . . .
F1 F -1.3600(9) -0.3814(4) 1.113(3) 0.055(4) Uani 1 1 d . . . . .
F2 F -1.2860(9) -0.3157(3) 0.905(3) 0.071(4) Uani 1 1 d . . . . .
F3 F -1.1816(11) -0.3703(5) 1.126(4) 0.077(6) Uani 1 1 d . . . . .
F4 F -1.1748(10) -0.3672(5) 0.693(3) 0.070(5) Uani 1 1 d . . . . .
F5 F -1.2537(9) -0.4327(4) 0.891(3) 0.070(4) Uani 1 1 d . . . . .
F6 F -1.3560(10) -0.3779(5) 0.670(4) 0.066(5) Uani 1 1 d . . . . .
Ag1 Ag -0.76777(12) -0.37563(6) 0.6563(3) 0.0448(6) Uani 1 1 d . . . . .
N1 N -0.8470(13) -0.3668(6) 0.937(4) 0.043(6) Uani 1 1 d . . . . .
H1 H -0.818043 -0.362734 1.064282 0.052 Uiso 1 1 calc R . . . .
N2 N -0.6865(14) -0.3844(6) 0.374(5) 0.047(6) Uani 1 1 d . . . . .
H2 H -0.714351 -0.389228 0.246188 0.057 Uiso 1 1 calc R . . . .
N3 N -0.9860(12) -0.3926(5) 0.799(3) 0.041(5) Uani 1 1 d . . . . .
H3 H -1.032680 -0.403033 0.872492 0.049 Uiso 1 1 d R . . . .
N4 N -0.9898(13) -0.3423(6) 1.075(3) 0.044(5) Uani 1 1 d . . . . .
H4 H -1.048649 -0.346904 1.067320 0.052 Uiso 1 1 calc R . . . .
N5 N -0.5519(12) -0.3576(5) 0.502(3) 0.035(5) Uani 1 1 d . . . . .
H5A H -0.492553 -0.359377 0.488107 0.041 Uiso 1 1 calc R . . . .
N6 N -0.5465(12) -0.4079(5) 0.233(3) 0.039(5) Uani 1 1 d . . . . .
H6A H -0.487562 -0.403865 0.242917 0.047 Uiso 1 1 calc R . . . .
C1 C -0.9361(14) -0.3668(6) 0.947(3) 0.032(5) Uani 1 1 d . . . . .
C2 C -0.9600(14) -0.3094(6) 1.222(4) 0.034(6) Uani 1 1 d . . . . .
C3 C -0.9991(15) -0.3046(6) 1.419(4) 0.042(6) Uani 1 1 d . . . . .
H3A H -1.044421 -0.324432 1.462410 0.050 Uiso 1 1 calc R . . . .
C4 C -0.9775(17) -0.2720(8) 1.568(4) 0.047(7) Uani 1 1 d . . . . .
H4A H -1.009212 -0.268833 1.705721 0.057 Uiso 1 1 calc R . . . .
C5 C -0.908(2) -0.2443(7) 1.508(5) 0.053(8) Uani 1 1 d . . . . .
H5 H -0.887690 -0.222790 1.608620 0.064 Uiso 1 1 calc R . . . .
C6 C -0.8683(18) -0.2486(8) 1.302(6) 0.050(7) Uani 1 1 d . . . . .
H6 H -0.822504 -0.229135 1.258429 0.060 Uiso 1 1 calc R . . . .
C7 C -0.8931(12) -0.2805(6) 1.156(4) 0.035(5) Uani 1 1 d . . . . .
H7 H -0.865291 -0.282784 1.013209 0.042 Uiso 1 1 calc R . . . .
C8 C -0.9537(15) -0.4243(6) 0.654(5) 0.044(6) Uani 1 1 d . . . . .
C9 C -0.8782(16) -0.4505(6) 0.709(4) 0.045(6) Uani 1 1 d . . . . .
H9 H -0.847408 -0.448038 0.847521 0.054 Uiso 1 1 calc R . . . .
C10 C -0.8519(16) -0.4800(7) 0.546(5) 0.049(8) Uani 1 1 d . . . . .
H10 H -0.801636 -0.497979 0.576473 0.058 Uiso 1 1 calc R . . . .
C11 C -0.8960(17) -0.4840(7) 0.344(5) 0.051(7) Uani 1 1 d . . . . .
H11 H -0.875775 -0.504205 0.236996 0.061 Uiso 1 1 calc R . . . .
C12 C -0.9691(17) -0.4587(7) 0.299(4) 0.049(7) Uani 1 1 d . . . . .
H12 H -1.000971 -0.461960 0.161618 0.059 Uiso 1 1 calc R . . . .
C13 C -0.9967(15) -0.4286(7) 0.451(4) 0.042(6) Uani 1 1 d . . . . .
H13 H -1.046096 -0.410493 0.415071 0.051 Uiso 1 1 calc R . . . .
C14 C -0.5996(15) -0.3835(6) 0.370(4) 0.035(5) Uani 1 1 d . . . . .
C15 C -0.5835(12) -0.3272(5) 0.665(4) 0.028(5) Uani 1 1 d . . . . .
C16 C -0.6580(13) -0.3002(7) 0.600(4) 0.041(6) Uani 1 1 d . . . . .
H16 H -0.686633 -0.303002 0.458563 0.049 Uiso 1 1 calc R . . . .
C17 C -0.6855(16) -0.2703(7) 0.751(4) 0.042(6) Uani 1 1 d . . . . .
H17 H -0.732624 -0.251113 0.712083 0.051 Uiso 1 1 calc R . . . .
C18 C -0.6458(16) -0.2675(7) 0.961(4) 0.044(7) Uani 1 1 d . . . . .
H18 H -0.668229 -0.247786 1.068323 0.052 Uiso 1 1 calc R . . . .
C19 C -0.5742(15) -0.2932(6) 1.013(4) 0.041(6) Uani 1 1 d . . . . .
H19 H -0.544734 -0.290453 1.153784 0.050 Uiso 1 1 calc R . . . .
C20 C -0.5448(14) -0.3228(6) 0.863(4) 0.037(5) Uani 1 1 d . . . . .
H20 H -0.495397 -0.340700 0.902015 0.045 Uiso 1 1 calc R . . . .
C21 C -0.5765(14) -0.4400(7) 0.074(4) 0.038(6) Uani 1 1 d . . . . .
C22 C -0.5349(14) -0.4430(6) -0.131(4) 0.032(5) Uani 1 1 d . . . . .
H22 H -0.489314 -0.423300 -0.173480 0.039 Uiso 1 1 calc R . . . .
C23 C -0.5605(15) -0.4754(6) -0.274(4) 0.042(6) Uani 1 1 d . . . . .
H23 H -0.531762 -0.477956 -0.415264 0.050 Uiso 1 1 calc R . . . .
C24 C -0.6277(16) -0.5043(7) -0.213(5) 0.044(7) Uani 1 1 d . . . . .
H24 H -0.643890 -0.526392 -0.313731 0.052 Uiso 1 1 calc R . . . .
C25 C -0.6698(17) -0.5014(7) -0.014(4) 0.045(7) Uani 1 1 d . . . . .
H25 H -0.717836 -0.520381 0.019753 0.054 Uiso 1 1 calc R . . . .
C26 C -0.6433(13) -0.4699(6) 0.147(4) 0.040(5) Uani 1 1 d . . . . .
H26 H -0.668532 -0.469084 0.293622 0.048 Uiso 1 1 calc R . . . .


_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
Sb1 F1 1.874(14) . ?
Sb1 F2 1.862(11) . ?
Sb1 F3 1.87(2) . ?
Sb1 F4 1.862(16) . ?
Sb1 F5 1.855(12) . ?
Sb1 F6 1.884(19) . ?
Ag1 N1 2.06(2) . ?
Ag1 N2 2.09(3) . ?
N1 C1 1.31(3) . ?
N2 C14 1.28(3) . ?
N3 C1 1.41(3) . ?
N3 C8 1.41(3) . ?
N4 C1 1.35(2) . ?
N4 C2 1.43(3) . ?
N5 C14 1.34(3) . ?
N5 C15 1.44(2) . ?
N6 C14 1.37(3) . ?
N6 C21 1.46(3) . ?
C2 C3 1.32(3) . ?
C2 C7 1.40(3) . ?
C3 C4 1.39(3) . ?
C4 C5 1.40(3) . ?
C5 C6 1.37(4) . ?
C6 C7 1.38(3) . ?
C8 C9 1.42(3) . ?
C8 C13 1.38(3) . ?
C9 C10 1.40(3) . ?
C10 C11 1.38(3) . ?
C11 C12 1.37(3) . ?
C12 C13 1.38(3) . ?
C15 C16 1.44(3) . ?
C15 C20 1.32(3) . ?
C16 C17 1.37(3) . ?
C17 C18 1.39(3) . ?
C18 C19 1.37(3) . ?
C19 C20 1.36(3) . ?
C21 C22 1.37(3) . ?
C21 C26 1.43(3) . ?
C22 C23 1.38(3) . ?
C23 C24 1.39(3) . ?
C24 C25 1.34(3) . ?
C25 C26 1.44(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
F1 Sb1 F6 89.7(6) . . ?
F2 Sb1 F1 90.3(6) . . ?
F2 Sb1 F3 90.9(8) . . ?
F2 Sb1 F6 88.9(7) . . ?
F3 Sb1 F1 90.3(8) . . ?
F3 Sb1 F6 179.8(8) . . ?
F4 Sb1 F1 178.2(7) . . ?
F4 Sb1 F2 89.9(7) . . ?
F4 Sb1 F3 88.0(7) . . ?
F4 Sb1 F6 92.1(8) . . ?
F5 Sb1 F1 89.0(6) . . ?
F5 Sb1 F2 178.7(6) . . ?
F5 Sb1 F3 90.2(7) . . ?
F5 Sb1 F4 90.9(6) . . ?
F5 Sb1 F6 90.1(7) . . ?
N1 Ag1 N2 179.4(9) . . ?
C1 N1 Ag1 126.8(19) . . ?
C14 N2 Ag1 126(2) . . ?
C1 N3 C8 128.3(18) . . ?
C1 N4 C2 125.8(19) . . ?
C14 N5 C15 129.3(17) . . ?
C14 N6 C21 127.4(18) . . ?
N1 C1 N3 119.7(19) . . ?
N1 C1 N4 128(2) . . ?
N4 C1 N3 112.4(18) . . ?
C3 C2 N4 120(2) . . ?
C3 C2 C7 119(2) . . ?
C7 C2 N4 121(2) . . ?
C2 C3 C4 124(2) . . ?
C3 C4 C5 118(2) . . ?
C6 C5 C4 119(3) . . ?
C5 C6 C7 122(3) . . ?
C6 C7 C2 119(2) . . ?
N3 C8 C9 122(2) . . ?
C13 C8 N3 117(2) . . ?
C13 C8 C9 120(2) . . ?
C10 C9 C8 116(2) . . ?
C11 C10 C9 123(2) . . ?
C12 C11 C10 119(2) . . ?
C11 C12 C13 120(3) . . ?
C12 C13 C8 121(2) . . ?
N2 C14 N5 122(2) . . ?
N2 C14 N6 125(2) . . ?
N5 C14 N6 113.3(19) . . ?
C16 C15 N5 117(2) . . ?
C20 C15 N5 122.3(19) . . ?
C20 C15 C16 120(2) . . ?
C17 C16 C15 117(2) . . ?
C16 C17 C18 121(2) . . ?
C19 C18 C17 120(2) . . ?
C20 C19 C18 120(2) . . ?
C15 C20 C19 122(2) . . ?
C22 C21 N6 120(2) . . ?
C22 C21 C26 122(2) . . ?
C26 C21 N6 118(2) . . ?
C21 C22 C23 119(2) . . ?
C22 C23 C24 121(2) . . ?
C25 C24 C23 121(2) . . ?
C24 C25 C26 121(2) . . ?
C21 C26 C25 116(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_d8v19290
_database_code_depnum_ccdc_archive 'CCDC 1907983'
loop_
_audit_author_name
_audit_author_address
'Feng Zhou'
;East China Normal University
China
;
_audit_update_record             
;
2019-04-11 deposited with the CCDC.	2019-11-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H15 N3 O3'
_chemical_formula_weight         273.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, 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'
'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'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -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'
'-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'

_cell_length_a                   34.5947(14)
_cell_length_b                   34.5947(14)
_cell_length_c                   10.7422(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     11133.8(10)
_cell_formula_units_Z            18
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    3562
_cell_measurement_theta_min      4.710
_cell_measurement_theta_max      48.761

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.734
_exptl_crystal_F_000             2592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.053
_shelx_estimated_absorpt_T_min   0.992
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5782
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12749
_diffrn_reflns_av_unetI/netI     0.1178
_diffrn_reflns_av_R_equivalents  0.0794
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.014
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.869
_diffrn_measured_fraction_theta_full 0.844
_diffrn_reflns_Laue_measured_fraction_max 0.869
_diffrn_reflns_Laue_measured_fraction_full 0.844
_diffrn_reflns_point_group_measured_fraction_max 0.869
_diffrn_reflns_point_group_measured_fraction_full 0.844
_reflns_number_total             3789
_reflns_number_gt                1911
_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. 
  
 _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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=exp[2.0000(sinθ/λ)²)]/[σ²(Fo²)+(0.1105P)²] 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     SHELXL
_refine_ls_extinction_coef       0.0017(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3789
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1169
_refine_ls_R_factor_gt           0.0784
_refine_ls_wR_factor_ref         0.2122
_refine_ls_wR_factor_gt          0.1955
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 -0.011 1813 320 ' '
2 0.333 0.667 0.032 1814 321 ' '
3 0.667 0.333 0.699 1814 321 ' '
_platon_squeeze_details          
;
;


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.44458(7) 0.40549(6) 0.13809(18) 0.0532(6) Uani 1 1 d . . . . .
O2 O 0.49984(7) 0.44643(7) 0.0096(2) 0.0589(6) Uani 1 1 d . . . . .
H2A H 0.5110 0.4711 -0.0274 0.088 Uiso 1 1 calc R U . . .
O3 O 0.46499(7) 0.47675(7) 0.10708(19) 0.0584(6) Uani 1 1 d . . . . .
N1 N 0.34815(8) 0.43404(9) 0.3996(2) 0.0591(7) Uani 1 1 d . . . . .
H1A H 0.3553 0.4568 0.4495 0.071 Uiso 1 1 calc R U . . .
H1B H 0.3209 0.4109 0.4009 0.071 Uiso 1 1 calc R U . . .
N2 N 0.41973(8) 0.46938(8) 0.3190(2) 0.0541(7) Uani 1 1 d . . . . .
H2 H 0.4347 0.4722 0.2502 0.065 Uiso 1 1 calc R U . . .
N3 N 0.36912(8) 0.40127(8) 0.2432(2) 0.0514(6) Uani 1 1 d . . . . .
H3 H 0.3923 0.4025 0.2051 0.062 Uiso 1 1 calc R U . . .
C1 C 0.37807(9) 0.43465(9) 0.3233(2) 0.0476(7) Uani 1 1 d . . . . .
C2 C 0.44244(9) 0.50195(10) 0.4111(3) 0.0512(7) Uani 1 1 d . . . . .
C3 C 0.47051(11) 0.54576(10) 0.3737(3) 0.0671(9) Uani 1 1 d . . . . .
H3A H 0.4716 0.5534 0.2883 0.080 Uiso 1 1 calc R U . . .
C4 C 0.49645(12) 0.57788(12) 0.4575(4) 0.0768(11) Uani 1 1 d . . . . .
H4 H 0.5160 0.6075 0.4302 0.092 Uiso 1 1 calc R U . . .
C5 C 0.49427(12) 0.56733(12) 0.5818(3) 0.0719(10) Uani 1 1 d . . . . .
H5 H 0.5120 0.5898 0.6405 0.086 Uiso 1 1 calc R U . . .
C6 C 0.46661(12) 0.52452(12) 0.6208(3) 0.0691(9) Uani 1 1 d . . . . .
H6 H 0.4652 0.5173 0.7066 0.083 Uiso 1 1 calc R U . . .
C7 C 0.44065(11) 0.49174(10) 0.5354(3) 0.0593(8) Uani 1 1 d . . . . .
H7 H 0.4215 0.4620 0.5629 0.071 Uiso 1 1 calc R U . . .
C8 C 0.32703(10) 0.36446(10) 0.2131(2) 0.0534(8) Uani 1 1 d . . . . .
C9 C 0.32372(13) 0.32235(11) 0.2087(3) 0.0682(9) Uani 1 1 d . . . . .
H9 H 0.3483 0.3188 0.2313 0.082 Uiso 1 1 calc R U . . .
C10 C 0.28449(16) 0.28669(12) 0.1712(3) 0.0851(13) Uani 1 1 d . . . . .
H10 H 0.2823 0.2583 0.1661 0.102 Uiso 1 1 calc R U . . .
C11 C 0.24814(14) 0.29032(13) 0.1409(3) 0.0833(12) Uani 1 1 d . . . . .
H11 H 0.2213 0.2648 0.1142 0.100 Uiso 1 1 calc R U . . .
C12 C 0.25052(13) 0.33139(15) 0.1492(3) 0.0820(12) Uani 1 1 d . . . . .
H12 H 0.2249 0.3339 0.1321 0.098 Uiso 1 1 calc R U . . .
C13 C 0.29064(11) 0.36902(12) 0.1828(3) 0.0641(9) Uani 1 1 d . . . . .
H13 H 0.2930 0.3976 0.1848 0.077 Uiso 1 1 calc R U . . .
C14 C 0.46822(9) 0.44277(9) 0.0879(2) 0.0467(7) Uani 1 1 d . . . . .


_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
O1 C14 1.252(3) . ?
O2 C14 1.335(3) . ?
O2 H2A 0.8400 . ?
O3 C14 1.252(3) . ?
N1 C1 1.312(4) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N2 C1 1.338(4) . ?
N2 C2 1.408(4) . ?
N2 H2 0.8800 . ?
N3 C1 1.346(3) . ?
N3 C8 1.411(4) . ?
N3 H3 0.8800 . ?
C2 C7 1.375(4) . ?
C2 C3 1.389(4) . ?
C3 C4 1.361(5) . ?
C3 H3A 0.9500 . ?
C4 C5 1.376(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.367(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.384(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C13 1.383(5) . ?
C8 C9 1.404(5) . ?
C9 C10 1.360(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.365(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.385(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.394(5) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?

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
C14 O2 H2A 109.5 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C1 N2 C2 127.9(2) . . ?
C1 N2 H2 116.1 . . ?
C2 N2 H2 116.1 . . ?
C1 N3 C8 127.7(2) . . ?
C1 N3 H3 116.2 . . ?
C8 N3 H3 116.2 . . ?
N1 C1 N2 121.5(2) . . ?
N1 C1 N3 123.0(3) . . ?
N2 C1 N3 115.5(2) . . ?
C7 C2 C3 118.6(3) . . ?
C7 C2 N2 122.8(3) . . ?
C3 C2 N2 118.4(2) . . ?
C4 C3 C2 121.0(3) . . ?
C4 C3 H3A 119.5 . . ?
C2 C3 H3A 119.5 . . ?
C3 C4 C5 119.9(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.1(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 120.0(3) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C2 C7 C6 120.4(3) . . ?
C2 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C13 C8 C9 120.2(3) . . ?
C13 C8 N3 122.6(3) . . ?
C9 C8 N3 117.1(3) . . ?
C10 C9 C8 118.6(4) . . ?
C10 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
C9 C10 C11 122.3(4) . . ?
C9 C10 H10 118.8 . . ?
C11 C10 H10 118.8 . . ?
C10 C11 C12 119.6(3) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C13 119.7(4) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C8 C13 C12 119.5(4) . . ?
C8 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
O1 C14 O3 125.2(2) . . ?
O1 C14 O2 116.8(2) . . ?
O3 C14 O2 117.9(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
C2 N2 C1 N1 21.2(5) . . . . ?
C2 N2 C1 N3 -159.8(3) . . . . ?
C8 N3 C1 N1 10.0(5) . . . . ?
C8 N3 C1 N2 -168.9(3) . . . . ?
C1 N2 C2 C7 42.8(5) . . . . ?
C1 N2 C2 C3 -142.2(3) . . . . ?
C7 C2 C3 C4 1.3(5) . . . . ?
N2 C2 C3 C4 -173.9(3) . . . . ?
C2 C3 C4 C5 -1.6(6) . . . . ?
C3 C4 C5 C6 1.0(6) . . . . ?
C4 C5 C6 C7 -0.2(6) . . . . ?
C3 C2 C7 C6 -0.5(5) . . . . ?
N2 C2 C7 C6 174.5(3) . . . . ?
C5 C6 C7 C2 0.0(5) . . . . ?
C1 N3 C8 C13 48.2(4) . . . . ?
C1 N3 C8 C9 -135.0(3) . . . . ?
C13 C8 C9 C10 1.5(5) . . . . ?
N3 C8 C9 C10 -175.3(3) . . . . ?
C8 C9 C10 C11 -1.6(5) . . . . ?
C9 C10 C11 C12 -0.7(6) . . . . ?
C10 C11 C12 C13 3.1(6) . . . . ?
C9 C8 C13 C12 0.8(5) . . . . ?
N3 C8 C13 C12 177.5(3) . . . . ?
C11 C12 C13 C8 -3.1(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3 O1 0.88 1.90 2.780(3) 174.5 .
N2 H2 O3 0.88 1.82 2.701(3) 178.8 .
N1 H1B O1 0.88 1.97 2.789(3) 155.0 5
O2 H2A O3 0.84 1.78 2.623(3) 179.4 10_665
N3 H3 O1 0.88 1.90 2.780(3) 174.5 .
N2 H2 O3 0.88 1.82 2.701(3) 178.8 .
N1 H1B O1 0.88 1.97 2.789(3) 155.0 5
O2 H2A O3 0.84 1.78 2.623(3) 179.4 10_665
O2 H2A O3 0.84 1.78 2.623(3) 179.4 10_665
N1 H1B O1 0.88 1.97 2.789(3) 155.0 5
N2 H2 O3 0.88 1.82 2.701(3) 178.8 .
N3 H3 O1 0.88 1.90 2.780(3) 174.5 .
O2 H2A O3 0.84 1.78 2.623(3) 179.4 10_665
N1 H1B O1 0.88 1.97 2.789(3) 155.0 5
N2 H2 O3 0.88 1.82 2.701(3) 178.8 .
N3 H3 O1 0.88 1.90 2.780(3) 174.5 .

_refine_diff_density_max         0.198
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.049

_shelxl_version_number           2013-4

