# Electronic Supplementary Material (ESI) for ChemComm.
# 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_HM_BD_ZG6_a
_database_code_depnum_ccdc_archive 'CCDC 1911202'
loop_
_audit_author_name
_audit_author_address
'Mohammad Mir'
;Aliah University
India
;
_audit_update_record             
;
2019-04-19 deposited with the CCDC.	2019-08-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H19 N O4 Zn'
_chemical_formula_weight         426.75

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'
'-x, -y, -z'

_cell_length_a                   7.8987(7)
_cell_length_b                   11.2682(10)
_cell_length_c                   11.2825(10)
_cell_angle_alpha                74.239(3)
_cell_angle_beta                 70.908(3)
_cell_angle_gamma                87.139(3)
_cell_volume                     912.44(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    105(2)
_cell_measurement_reflns_used    7414
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      27.11

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.112
_exptl_crystal_size_mid          0.104
_exptl_crystal_size_min          0.098
_exptl_absorpt_coefficient_mu    1.375
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      105(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            8010
_diffrn_reflns_av_unetI/netI     0.0832
_diffrn_reflns_av_R_equivalents  0.1173
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.335
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             3141
_reflns_number_gt                3027
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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=1/[σ²(Fo²)+(0.1000P)²+0.2103P] 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-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.126(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3141
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.1293
_refine_ls_wR_factor_gt          0.1280
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_restrained_S_all      0.968
_refine_ls_shift/su_max          0.001
_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
Zn1 Zn 0.00912(3) 0.90332(2) 0.93366(2) 0.0152(2) Uani 1 1 d . . . . .
O1 O 0.2105(3) 1.02241(18) 0.8034(2) 0.0250(4) Uani 1 1 d . . . . .
O2 O 0.1893(3) 1.17631(17) 0.89572(19) 0.0244(4) Uani 1 1 d . . . . .
O4 O 0.8201(3) 1.01259(17) 0.8751(2) 0.0272(5) Uani 1 1 d . . . . .
N1 N 0.0289(3) 0.7701(2) 0.8390(2) 0.0169(5) Uani 1 1 d . . . . .
O3 O 0.8156(3) 1.16528(19) 0.9668(2) 0.0286(5) Uani 1 1 d . . . . .
C13 C 0.3044(3) 0.3566(2) 0.3779(2) 0.0176(5) Uani 1 1 d . . . . .
C5 C 0.1466(4) 0.7777(2) 0.7199(3) 0.0222(6) Uani 1 1 d . . . . .
H5 H 0.215408 0.852574 0.672887 0.027 Uiso 1 1 calc R U . . .
C8 C 0.1839(3) 0.3527(2) 0.5058(3) 0.0175(6) Uani 1 1 d . . . . .
C22 C 0.7609(3) 1.1111(2) 0.9023(2) 0.0188(5) Uani 1 1 d . . . . .
C12 C 0.3207(3) 0.2477(2) 0.3340(3) 0.0205(6) Uani 1 1 d . . . . .
C9 C 0.0848(4) 0.2458(2) 0.5799(3) 0.0195(6) Uani 1 1 d . . . . .
H9 H 0.001949 0.244415 0.663232 0.023 Uiso 1 1 calc R U . . .
C18 C 0.2613(3) 1.1244(2) 0.8070(2) 0.0167(5) Uani 1 1 d . . . . .
C7 C 0.1671(4) 0.4616(2) 0.5566(3) 0.0205(6) Uani 1 1 d . . . . .
H7 H 0.212568 0.538725 0.495499 0.025 Uiso 1 1 calc R U . . .
C6 C 0.0933(4) 0.4608(2) 0.6814(3) 0.0224(6) Uani 1 1 d . . . . .
H6 H 0.050641 0.383624 0.743152 0.027 Uiso 1 1 calc R U . . .
C1 C -0.0670(4) 0.6640(3) 0.9040(3) 0.0262(6) Uani 1 1 d . . . . .
H1 H -0.151261 0.657659 0.988032 0.031 Uiso 1 1 calc R U . . .
C10 C 0.1011(3) 0.1386(2) 0.5374(3) 0.0210(6) Uani 1 1 d . . . . .
H10 H 0.031966 0.065768 0.592159 0.025 Uiso 1 1 calc R U . . .
C19 C 0.4298(3) 1.1863(2) 0.6997(3) 0.0202(5) Uani 1 1 d . . . . .
H19A H 0.427864 1.276722 0.687602 0.024 Uiso 1 1 calc R U . . .
H19B H 0.435125 1.170031 0.616702 0.024 Uiso 1 1 calc R U . . .
C4 C 0.1717(4) 0.6819(2) 0.6635(3) 0.0220(6) Uani 1 1 d . . . . .
H4 H 0.256022 0.691455 0.578830 0.026 Uiso 1 1 calc R U . . .
C3 C 0.0734(4) 0.5706(2) 0.7300(3) 0.0194(6) Uani 1 1 d . . . . .
C11 C 0.2173(4) 0.1394(2) 0.4164(3) 0.0233(6) Uani 1 1 d . . . . .
H11 H 0.228559 0.066669 0.387649 0.028 Uiso 1 1 calc R U . . .
C17 C 0.4404(4) 0.2499(3) 0.2081(3) 0.0260(6) Uani 1 1 d . . . . .
H17 H 0.451435 0.177474 0.178825 0.031 Uiso 1 1 calc R U . . .
C21 C 0.6083(3) 1.1696(2) 0.8550(3) 0.0218(6) Uani 1 1 d . . . . .
H21A H 0.493730 1.144608 0.927183 0.026 Uiso 1 1 calc R U . . .
H21B H 0.623803 1.260494 0.833551 0.026 Uiso 1 1 calc R U . . .
C14 C 0.4106(4) 0.4624(2) 0.2918(3) 0.0225(6) Uani 1 1 d . . . . .
H14 H 0.403356 0.535662 0.319186 0.027 Uiso 1 1 calc R U . . .
C20 C 0.5947(3) 1.1358(2) 0.7367(3) 0.0213(6) Uani 1 1 d . . . . .
H20A H 0.590205 1.044822 0.754744 0.026 Uiso 1 1 calc R U . . .
H20B H 0.703897 1.168232 0.661677 0.026 Uiso 1 1 calc R U . . .
C2 C -0.0483(4) 0.5635(3) 0.8537(3) 0.0276(6) Uani 1 1 d . . . . .
H2 H -0.118219 0.489575 0.903247 0.033 Uiso 1 1 calc R U . . .
C16 C 0.5397(4) 0.3541(3) 0.1284(3) 0.0283(6) Uani 1 1 d . . . . .
H16 H 0.619805 0.353933 0.044664 0.034 Uiso 1 1 calc R U . . .
C15 C 0.5228(4) 0.4623(2) 0.1708(3) 0.0266(6) Uani 1 1 d . . . . .
H15 H 0.590120 0.535411 0.114729 0.032 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
Zn1 O1 2.0256(19) . ?
Zn1 N1 2.039(2) . ?
Zn1 O2 2.048(2) 2_577 ?
Zn1 O4 2.0493(18) 1_455 ?
Zn1 O3 2.0528(18) 2_677 ?
Zn1 Zn1 2.9339(5) 2_577 ?
O1 C18 1.251(3) . ?
O2 C18 1.257(3) . ?
O4 C22 1.259(3) . ?
N1 C1 1.338(4) . ?
N1 C5 1.344(4) . ?
O3 C22 1.250(3) . ?
C13 C14 1.416(4) . ?
C13 C12 1.428(4) . ?
C13 C8 1.436(4) . ?
C5 C4 1.371(4) . ?
C5 H5 0.9500 . ?
C8 C9 1.371(4) . ?
C8 C7 1.473(4) . ?
C22 C21 1.524(3) . ?
C12 C11 1.417(4) . ?
C12 C17 1.420(4) . ?
C9 C10 1.402(4) . ?
C9 H9 0.9500 . ?
C18 C19 1.518(3) . ?
C7 C6 1.334(4) . ?
C7 H7 0.9500 . ?
C6 C3 1.466(4) . ?
C6 H6 0.9500 . ?
C1 C2 1.380(4) . ?
C1 H1 0.9500 . ?
C10 C11 1.371(4) . ?
C10 H10 0.9500 . ?
C19 C20 1.532(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C4 C3 1.394(4) . ?
C4 H4 0.9500 . ?
C3 C2 1.396(4) . ?
C11 H11 0.9500 . ?
C17 C16 1.364(4) . ?
C17 H17 0.9500 . ?
C21 C20 1.520(4) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C14 C15 1.363(4) . ?
C14 H14 0.9500 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C2 H2 0.9500 . ?
C16 C15 1.411(4) . ?
C16 H16 0.9500 . ?
C15 H15 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
O1 Zn1 N1 100.13(9) . . ?
O1 Zn1 O2 159.54(9) . 2_577 ?
N1 Zn1 O2 99.96(9) . 2_577 ?
O1 Zn1 O4 91.56(8) . 1_455 ?
N1 Zn1 O4 101.82(8) . 1_455 ?
O2 Zn1 O4 88.13(8) 2_577 1_455 ?
O1 Zn1 O3 87.48(8) . 2_677 ?
N1 Zn1 O3 98.12(8) . 2_677 ?
O2 Zn1 O3 85.87(8) 2_577 2_677 ?
O4 Zn1 O3 159.89(9) 1_455 2_677 ?
O1 Zn1 Zn1 78.53(6) . 2_577 ?
N1 Zn1 Zn1 178.47(7) . 2_577 ?
O2 Zn1 Zn1 81.34(5) 2_577 2_577 ?
O4 Zn1 Zn1 79.00(6) 1_455 2_577 ?
O3 Zn1 Zn1 81.13(6) 2_677 2_577 ?
C18 O1 Zn1 129.84(18) . . ?
C18 O2 Zn1 124.66(16) . 2_577 ?
C22 O4 Zn1 128.52(17) . 1_655 ?
C1 N1 C5 117.9(2) . . ?
C1 N1 Zn1 118.24(19) . . ?
C5 N1 Zn1 123.51(18) . . ?
C22 O3 Zn1 125.54(17) . 2_677 ?
C14 C13 C12 117.4(2) . . ?
C14 C13 C8 123.9(2) . . ?
C12 C13 C8 118.7(2) . . ?
N1 C5 C4 122.8(3) . . ?
N1 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
C9 C8 C13 118.9(2) . . ?
C9 C8 C7 120.5(3) . . ?
C13 C8 C7 120.5(2) . . ?
O3 C22 O4 125.3(2) . . ?
O3 C22 C21 116.5(2) . . ?
O4 C22 C21 118.2(2) . . ?
C11 C12 C17 121.0(2) . . ?
C11 C12 C13 119.6(2) . . ?
C17 C12 C13 119.4(2) . . ?
C8 C9 C10 122.5(3) . . ?
C8 C9 H9 118.8 . . ?
C10 C9 H9 118.8 . . ?
O1 C18 O2 125.2(2) . . ?
O1 C18 C19 117.1(2) . . ?
O2 C18 C19 117.6(2) . . ?
C6 C7 C8 125.3(3) . . ?
C6 C7 H7 117.3 . . ?
C8 C7 H7 117.3 . . ?
C7 C6 C3 124.7(3) . . ?
C7 C6 H6 117.7 . . ?
C3 C6 H6 117.7 . . ?
N1 C1 C2 122.6(3) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C11 C10 C9 119.7(2) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C18 C19 C20 109.4(2) . . ?
C18 C19 H19A 109.8 . . ?
C20 C19 H19A 109.8 . . ?
C18 C19 H19B 109.8 . . ?
C20 C19 H19B 109.8 . . ?
H19A C19 H19B 108.2 . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C3 C2 116.7(2) . . ?
C4 C3 C6 124.9(3) . . ?
C2 C3 C6 118.4(3) . . ?
C10 C11 C12 120.5(2) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C16 C17 C12 121.2(3) . . ?
C16 C17 H17 119.4 . . ?
C12 C17 H17 119.4 . . ?
C20 C21 C22 114.8(2) . . ?
C20 C21 H21A 108.6 . . ?
C22 C21 H21A 108.6 . . ?
C20 C21 H21B 108.6 . . ?
C22 C21 H21B 108.6 . . ?
H21A C21 H21B 107.5 . . ?
C15 C14 C13 122.0(2) . . ?
C15 C14 H14 119.0 . . ?
C13 C14 H14 119.0 . . ?
C21 C20 C19 113.3(2) . . ?
C21 C20 H20A 108.9 . . ?
C19 C20 H20A 108.9 . . ?
C21 C20 H20B 108.9 . . ?
C19 C20 H20B 108.9 . . ?
H20A C20 H20B 107.7 . . ?
C1 C2 C3 119.9(3) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C17 C16 C15 119.7(3) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C14 C15 C16 120.4(3) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?

_refine_diff_density_max         0.901
_refine_diff_density_min         -0.972
_refine_diff_density_rms         0.118

####################################################################### 
# 
# 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_zg6_a
_database_code_depnum_ccdc_archive 'CCDC 1911203'
loop_
_audit_author_name
_audit_author_address
'Mohammad Mir'
;Aliah University
India
;
_audit_update_record             
;
2019-04-19 deposited with the CCDC.	2019-08-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C71 H60 N4 O'
_chemical_formula_weight         985.23

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.8251(15)
_cell_length_b                   15.8177(18)
_cell_length_c                   13.4161(15)
_cell_angle_alpha                90
_cell_angle_beta                 112.749(3)
_cell_angle_gamma                90
_cell_volume                     2705.6(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    7620
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      25.47

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_F_000             1044.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.111
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.098
_exptl_absorpt_coefficient_mu    0.071
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(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            34909
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.052
_diffrn_reflns_theta_max         27.193
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6015
_reflns_number_gt                3564
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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=1/[σ²(Fo²)+(0.1000P)²+0.5014P] 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_number_reflns         5978
_refine_ls_number_parameters     353
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1156
_refine_ls_R_factor_gt           0.0673
_refine_ls_wR_factor_ref         0.2273
_refine_ls_wR_factor_gt          0.1918
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_restrained_S_all      1.133
_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
C8 C 0.50168(17) 0.78980(14) 0.56066(17) 0.0514(5) Uani 1 1 d . . . . .
C7 C 0.42573(17) 0.73523(13) 0.58671(17) 0.0494(5) Uani 1 1 d . . . . .
H7 H 0.445438 0.676013 0.584045 0.059 Uiso 1 1 calc R U . . .
C25 C 0.24283(19) 0.65324(15) 0.65040(18) 0.0577(6) Uani 1 1 d . . . . .
C24 C 0.29017(18) 0.73468(14) 0.63237(18) 0.0540(5) Uani 1 1 d . . . . .
H24 H 0.250230 0.783026 0.641890 0.065 Uiso 1 1 calc R U . . .
C3 C 0.25277(17) 0.68201(15) 0.43267(16) 0.0524(5) Uani 1 1 d . . . . .
C13 C 0.61136(18) 0.77470(15) 0.61430(19) 0.0573(6) Uani 1 1 d . . . . .
C6 C 0.30663(17) 0.74339(14) 0.52244(17) 0.0508(5) Uani 1 1 d . . . . .
H6 H 0.290039 0.801279 0.495131 0.061 Uiso 1 1 calc R U . . .
C23 C 0.40909(19) 0.74941(14) 0.69525(18) 0.0549(6) Uani 1 1 d . . . . .
H23 H 0.440819 0.703805 0.747078 0.066 Uiso 1 1 calc R U . . .
N1 N 0.1460(2) 0.5677(2) 0.26543(19) 0.0855(8) Uani 1 1 d . . . . .
C9 C 0.4694(2) 0.85382(15) 0.48649(19) 0.0613(6) Uani 1 1 d . . . . .
H9 H 0.398013 0.864599 0.451191 0.074 Uiso 1 1 calc R U . . .
C4 C 0.28345(19) 0.59895(16) 0.43506(19) 0.0608(6) Uani 1 1 d . . . . .
H4 H 0.341111 0.579104 0.493467 0.073 Uiso 1 1 calc R U . . .
C20 C 0.43884(19) 0.83518(15) 0.74745(18) 0.0583(6) Uani 1 1 d . . . . .
N2 N 0.4952(3) 0.99272(18) 0.8517(2) 0.0957(9) Uani 1 1 d . . . . .
C12 C 0.6841(2) 0.82429(18) 0.5882(2) 0.0674(7) Uani 1 1 d . . . . .
C30 C 0.1310(2) 0.64595(18) 0.6094(2) 0.0696(7) Uani 1 1 d . . . . .
C2 C 0.1666(2) 0.70614(19) 0.3424(2) 0.0711(7) Uani 1 1 d . . . . .
H2 H 0.142391 0.761559 0.335238 0.085 Uiso 1 1 calc R U . . .
C14 C 0.6524(2) 0.71096(18) 0.6932(2) 0.0742(8) Uani 1 1 d . . . . .
H14 H 0.606580 0.677891 0.712126 0.089 Uiso 1 1 calc R U . . .
C26 C 0.3019(2) 0.58641(16) 0.7030(2) 0.0729(7) Uani 1 1 d . . . . .
H26 H 0.374530 0.590651 0.728101 0.087 Uiso 1 1 calc R U . . .
C10 C 0.5417(2) 0.90359(18) 0.4626(2) 0.0744(8) Uani 1 1 d . . . . .
H10 H 0.517672 0.947265 0.412626 0.089 Uiso 1 1 calc R U . . .
C5 C 0.2292(2) 0.54516(19) 0.3514(2) 0.0751(8) Uani 1 1 d . . . . .
H5 H 0.252318 0.489575 0.355543 0.090 Uiso 1 1 calc R U . . .
C19 C 0.5190(2) 0.84287(19) 0.8480(2) 0.0810(8) Uani 1 1 d . . . . .
H19 H 0.556328 0.795349 0.883057 0.097 Uiso 1 1 calc R U . . .
C21 C 0.3885(2) 0.90909(16) 0.7010(2) 0.0713(7) Uani 1 1 d . . . . .
H21 H 0.334016 0.907771 0.633214 0.086 Uiso 1 1 calc R U . . .
C11 C 0.6451(2) 0.8889(2) 0.5109(2) 0.0788(8) Uani 1 1 d . . . . .
H11 H 0.691609 0.922037 0.493066 0.095 Uiso 1 1 calc R U . . .
C22 C 0.4187(3) 0.98494(18) 0.7549(3) 0.0812(8) Uani 1 1 d . . . . .
H22 H 0.383216 1.033584 0.721316 0.097 Uiso 1 1 calc R U . . .
C1 C 0.1168(2) 0.6470(3) 0.2630(2) 0.0843(9) Uani 1 1 d . . . . .
H1 H 0.058559 0.664737 0.203599 0.101 Uiso 1 1 calc R U . . .
C31 C 0.0627(2) 0.7106(2) 0.5487(2) 0.0837(9) Uani 1 1 d . . . . .
H31 H 0.090511 0.760141 0.533432 0.100 Uiso 1 1 calc R U . . .
C17 C 0.7916(2) 0.8078(3) 0.6404(3) 0.0939(10) Uani 1 1 d . . . . .
H17 H 0.839045 0.840279 0.623145 0.113 Uiso 1 1 calc R U . . .
C18 C 0.5436(3) 0.9214(2) 0.8962(3) 0.1021(11) Uani 1 1 d . . . . .
H18 H 0.597423 0.924553 0.964286 0.122 Uiso 1 1 calc R U . . .
C29 C 0.0861(3) 0.5704(3) 0.6301(3) 0.0984(11) Uani 1 1 d . . . . .
C16 C 0.8282(3) 0.7459(3) 0.7150(3) 0.1063(12) Uani 1 1 d . . . . .
H16 H 0.899909 0.736036 0.748196 0.128 Uiso 1 1 calc R U . . .
C15 C 0.7577(2) 0.6967(2) 0.7423(3) 0.0958(10) Uani 1 1 d . . . . .
H15 H 0.782777 0.654220 0.793872 0.115 Uiso 1 1 calc R U . . .
C32 C -0.0442(3) 0.7008(3) 0.5123(3) 0.1147(14) Uani 1 1 d . . . . .
H32 H -0.087890 0.743941 0.472704 0.138 Uiso 1 1 calc R U . . .
C34 C -0.0250(4) 0.5646(4) 0.5900(4) 0.144(2) Uani 1 1 d . . . . .
H34 H -0.055418 0.515606 0.603084 0.173 Uiso 1 1 calc R U . . .
C33 C -0.0877(4) 0.6277(5) 0.5335(5) 0.148(2) Uani 1 1 d . . . . .
H33 H -0.160159 0.622096 0.508892 0.178 Uiso 1 1 calc R U . . .
O2 O 1.0725(13) 0.4519(8) 0.0947(10) 0.493(19) Uani 0.5 1 d D . P . .
H2A H 1.111247 0.484126 0.140811 0.739 Uiso 0.5 1 calc R U P . .
C100 C 0.9685(13) 0.4564(13) 0.0941(10) 0.567(19) Uani 1 1 d D . . . .
H10A H 0.958755 0.516948 0.083547 0.681 Uiso 1 1 calc R U . . .
H10B H 0.987435 0.449229 0.171144 0.681 Uiso 1 1 calc R U . . .
C101 C 0.8504(12) 0.4315(8) 0.0565(12) 0.238(9) Uani 0.5 1 d D . P . .
H10C H 0.815762 0.440978 -0.019899 0.356 Uiso 0.5 1 calc R U P . .
H10D H 0.817863 0.465440 0.094155 0.356 Uiso 0.5 1 calc R U P . .
H10E H 0.844923 0.372890 0.071982 0.356 Uiso 0.5 1 calc R U P . .
C27 C 0.2575(3) 0.5110(2) 0.7209(3) 0.1022(11) Uani 1 1 d . . . . .
H27 H 0.300591 0.466320 0.756758 0.123 Uiso 1 1 calc R U . . .
C28 C 0.1537(4) 0.5036(3) 0.6865(3) 0.1191(14) Uani 1 1 d . . . . .
H28 H 0.124929 0.453711 0.699603 0.143 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
C8 C9 1.368(3) . ?
C8 C13 1.425(3) . ?
C8 C7 1.501(3) . ?
C7 C6 1.541(3) . ?
C7 C23 1.576(3) . ?
C7 H7 0.9800 . ?
C25 C26 1.355(4) . ?
C25 C30 1.431(4) . ?
C25 C24 1.506(3) . ?
C24 C23 1.548(3) . ?
C24 C6 1.583(3) . ?
C24 H24 0.9800 . ?
C3 C4 1.377(3) . ?
C3 C2 1.384(3) . ?
C3 C6 1.501(3) . ?
C13 C14 1.412(4) . ?
C13 C12 1.422(3) . ?
C6 H6 0.9800 . ?
C23 C20 1.509(3) . ?
C23 H23 0.9800 . ?
N1 C1 1.315(4) . ?
N1 C5 1.325(4) . ?
C9 C10 1.404(4) . ?
C9 H9 0.9300 . ?
C4 C5 1.377(3) . ?
C4 H4 0.9300 . ?
C20 C21 1.380(4) . ?
C20 C19 1.381(3) . ?
N2 C22 1.326(4) . ?
N2 C18 1.330(4) . ?
C12 C17 1.401(4) . ?
C12 C11 1.407(4) . ?
C30 C31 1.416(4) . ?
C30 C29 1.422(4) . ?
C2 C1 1.385(4) . ?
C2 H2 0.9300 . ?
C14 C15 1.365(4) . ?
C14 H14 0.9300 . ?
C26 C27 1.403(4) . ?
C26 H26 0.9300 . ?
C10 C11 1.341(4) . ?
C10 H10 0.9300 . ?
C5 H5 0.9300 . ?
C19 C18 1.381(4) . ?
C19 H19 0.9300 . ?
C21 C22 1.380(4) . ?
C21 H21 0.9300 . ?
C11 H11 0.9300 . ?
C22 H22 0.9300 . ?
C1 H1 0.9300 . ?
C31 C32 1.374(4) . ?
C31 H31 0.9300 . ?
C17 C16 1.350(5) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C29 C28 1.420(6) . ?
C29 C34 1.420(6) . ?
C16 C15 1.402(5) . ?
C16 H16 0.9300 . ?
C15 H15 0.9300 . ?
C32 C33 1.384(7) . ?
C32 H32 0.9300 . ?
C34 C33 1.346(7) . ?
C34 H34 0.9300 . ?
C33 H33 0.9300 . ?
O2 C100 1.437(18) . ?
O2 H2A 0.8200 . ?
C100 C101 1.562(16) . ?
C100 H10A 0.9700 . ?
C100 H10B 0.9700 . ?
C101 H10C 0.9600 . ?
C101 H10D 0.9600 . ?
C101 H10E 0.9600 . ?
C27 C28 1.333(5) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?

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
C9 C8 C13 118.4(2) . . ?
C9 C8 C7 122.3(2) . . ?
C13 C8 C7 119.3(2) . . ?
C8 C7 C6 120.93(18) . . ?
C8 C7 C23 119.90(17) . . ?
C6 C7 C23 89.93(16) . . ?
C8 C7 H7 108.2 . . ?
C6 C7 H7 108.2 . . ?
C23 C7 H7 108.2 . . ?
C26 C25 C30 118.8(2) . . ?
C26 C25 C24 122.6(2) . . ?
C30 C25 C24 118.6(2) . . ?
C25 C24 C23 118.49(19) . . ?
C25 C24 C6 116.87(18) . . ?
C23 C24 C6 89.40(16) . . ?
C25 C24 H24 110.2 . . ?
C23 C24 H24 110.2 . . ?
C6 C24 H24 110.2 . . ?
C4 C3 C2 115.9(2) . . ?
C4 C3 C6 123.1(2) . . ?
C2 C3 C6 121.0(2) . . ?
C14 C13 C12 117.4(2) . . ?
C14 C13 C8 122.6(2) . . ?
C12 C13 C8 119.9(2) . . ?
C3 C6 C7 119.08(18) . . ?
C3 C6 C24 119.07(17) . . ?
C7 C6 C24 88.79(16) . . ?
C3 C6 H6 109.4 . . ?
C7 C6 H6 109.4 . . ?
C24 C6 H6 109.4 . . ?
C20 C23 C24 115.4(2) . . ?
C20 C23 C7 116.47(17) . . ?
C24 C23 C7 88.79(16) . . ?
C20 C23 H23 111.4 . . ?
C24 C23 H23 111.4 . . ?
C7 C23 H23 111.4 . . ?
C1 N1 C5 115.7(3) . . ?
C8 C9 C10 121.3(2) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C5 C4 C3 120.3(2) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C21 C20 C19 116.1(2) . . ?
C21 C20 C23 123.6(2) . . ?
C19 C20 C23 120.3(2) . . ?
C22 N2 C18 115.7(3) . . ?
C17 C12 C11 122.3(3) . . ?
C17 C12 C13 119.3(3) . . ?
C11 C12 C13 118.4(2) . . ?
C31 C30 C29 118.3(3) . . ?
C31 C30 C25 122.9(2) . . ?
C29 C30 C25 118.8(3) . . ?
C3 C2 C1 119.4(3) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C15 C14 C13 121.6(3) . . ?
C15 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C25 C26 C27 122.5(3) . . ?
C25 C26 H26 118.8 . . ?
C27 C26 H26 118.8 . . ?
C11 C10 C9 120.8(3) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
N1 C5 C4 124.0(3) . . ?
N1 C5 H5 118.0 . . ?
C4 C5 H5 118.0 . . ?
C18 C19 C20 119.8(3) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C22 C21 C20 120.2(3) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C10 C11 C12 121.0(2) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
N2 C22 C21 124.0(3) . . ?
N2 C22 H22 118.0 . . ?
C21 C22 H22 118.0 . . ?
N1 C1 C2 124.6(3) . . ?
N1 C1 H1 117.7 . . ?
C2 C1 H1 117.7 . . ?
C32 C31 C30 120.6(4) . . ?
C32 C31 H31 119.7 . . ?
C30 C31 H31 119.7 . . ?
C16 C17 C12 121.7(3) . . ?
C16 C17 H17 119.1 . . ?
C12 C17 H17 119.1 . . ?
N2 C18 C19 124.2(3) . . ?
N2 C18 H18 117.9 . . ?
C19 C18 H18 117.9 . . ?
C28 C29 C34 123.1(4) . . ?
C28 C29 C30 118.8(3) . . ?
C34 C29 C30 118.1(4) . . ?
C17 C16 C15 119.8(3) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C14 C15 C16 120.1(3) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C31 C32 C33 121.0(5) . . ?
C31 C32 H32 119.5 . . ?
C33 C32 H32 119.5 . . ?
C33 C34 C29 122.1(5) . . ?
C33 C34 H34 119.0 . . ?
C29 C34 H34 119.0 . . ?
C34 C33 C32 119.9(4) . . ?
C34 C33 H33 120.0 . . ?
C32 C33 H33 120.0 . . ?
C100 O2 H2A 109.5 . . ?
O2 C100 C101 155.3(16) . . ?
O2 C100 H10A 97.6 . . ?
C101 C100 H10A 97.6 . . ?
O2 C100 H10B 97.6 . . ?
C101 C100 H10B 97.6 . . ?
H10A C100 H10B 103.6 . . ?
C100 C101 H10C 109.5 . . ?
C100 C101 H10D 109.5 . . ?
H10C C101 H10D 109.5 . . ?
C100 C101 H10E 109.5 . . ?
H10C C101 H10E 109.5 . . ?
H10D C101 H10E 109.5 . . ?
C28 C27 C26 120.0(4) . . ?
C28 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
C27 C28 C29 121.1(3) . . ?
C27 C28 H28 119.4 . . ?
C29 C28 H28 119.4 . . ?

_refine_diff_density_max         0.344
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.040

