# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_mo_zri185_0m
_database_code_depnum_ccdc_archive 'CCDC 1530340'
_audit_update_record             
;
2017-01-30 deposited with the CCDC.
2017-02-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H27 N O4 S'
_chemical_formula_weight         413.51
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_space_group_IT_number           14
_symmetry_space_group_name_H-M   P2(1)/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                   9.4223(6)
_cell_length_b                   20.6490(13)
_cell_length_c                   10.9082(8)
_cell_angle_alpha                90
_cell_angle_beta                 105.9641(19)
_cell_angle_gamma                90
_cell_volume                     2040.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6461
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      32.05

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_exptl_absorpt_coefficient_mu    0.189
_shelx_estimated_absorpt_T_min   0.937
_shelx_estimated_absorpt_T_max   0.946
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.885
_exptl_absorpt_correction_T_max  0.946
_exptl_absorpt_process_details   
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_special_details           
; 
 It should be noted that the esd's of the cell dimensions are probably too low;
 they should be multiplied by a factor of 2 to 10
;
_diffrn_ambient_temperature      100(2)
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Microfocus source E025 IuS'
_diffrn_source_type              'Bruker APEX DUO'
_diffrn_source_power             50
_diffrn_source_current           0.6
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_radiation_monochromator  'Quazar MX Multilayer Optics'
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measurement_device_type  'APEX DUO Kappa 4-axis goniometer'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            14366
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.972
_diffrn_reflns_theta_max         32.427
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.880
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.880
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.880
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             6481
_reflns_number_gt                5535
_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 v2014.9-0'
_computing_cell_refinement       'Bruker APEX2 v2014.9-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_structure_solution    Sir2011
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0531P)²+0.8321P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6481
_refine_ls_number_parameters     269
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1111
_refine_ls_wR_factor_gt          0.1059
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
S1 S 0.20063(3) 0.19716(2) 0.76431(3) 0.01331(8) Uani 1 1 d . . . . .
N1 N 0.21127(11) 0.13368(4) 0.85638(9) 0.01232(18) Uani 1 1 d . . . . .
O1 O 0.36122(11) 0.04544(4) 1.40724(8) 0.01978(19) Uani 1 1 d . . . . .
O2 O 0.29330(11) -0.08792(4) 1.04474(8) 0.01960(19) Uani 1 1 d . . . . .
O3 O 0.29403(10) 0.24604(4) 0.83889(9) 0.01949(19) Uani 1 1 d . . . . .
O4 O 0.22761(11) 0.17513(4) 0.64829(9) 0.02041(19) Uani 1 1 d . . . . .
C1 C 0.19487(12) 0.01428(5) 0.86638(10) 0.01113(19) Uani 1 1 d . . . . .
C2 C 0.33232(13) -0.00190(6) 0.82092(11) 0.0138(2) Uani 1 1 d . . . . .
H2A H 0.3978 0.0365 0.8339 0.017 Uiso 1 1 calc R U . . .
H2B H 0.3874 -0.0376 0.8738 0.017 Uiso 1 1 calc R U . . .
C3 C 0.29442(15) -0.02144(7) 0.68320(13) 0.0226(3) Uani 1 1 d . . . . .
H3 H 0.3702(19) -0.0255(8) 0.6443(17) 0.023(4) Uiso 1 1 d . . . . .
C4 C 0.15726(15) -0.04370(6) 0.61994(12) 0.0189(2) Uani 1 1 d . . . . .
H4 H 0.1402 -0.0568 0.5336 0.023 Uiso 1 1 calc R U . . .
C5 C 0.03592(15) -0.04831(6) 0.67814(12) 0.0208(3) Uani 1 1 d . . . . .
H5A H -0.0111 -0.0913 0.6575 0.025 Uiso 1 1 calc R U . . .
H5B H -0.0388 -0.0152 0.6388 0.025 Uiso 1 1 calc R U . . .
C6 C 0.07785(13) -0.03943(5) 0.82165(11) 0.0148(2) Uani 1 1 d . . . . .
H6A H 0.1171 -0.0808 0.8634 0.018 Uiso 1 1 calc R U . . .
H6B H -0.0115 -0.0282 0.8482 0.018 Uiso 1 1 calc R U . . .
C7 C 0.12380(13) 0.07680(5) 0.80018(11) 0.0126(2) Uani 1 1 d . . . . .
H7A H 0.1170 0.0745 0.7081 0.015 Uiso 1 1 calc R U . . .
H7B H 0.0225 0.0810 0.8092 0.015 Uiso 1 1 calc R U . . .
C8 C 0.19704(13) 0.14546(5) 0.98491(11) 0.0134(2) Uani 1 1 d . . . . .
H8A H 0.0937 0.1570 0.9802 0.016 Uiso 1 1 calc R U . . .
H8B H 0.2612 0.1821 1.0244 0.016 Uiso 1 1 calc R U . . .
C9 C 0.24123(12) 0.08530(5) 1.06535(11) 0.01091(19) Uani 1 1 d . . . . .
C10 C 0.28231(12) 0.09548(5) 1.19727(11) 0.0131(2) Uani 1 1 d . . . . .
H10 H 0.2847 0.1380 1.2310 0.016 Uiso 1 1 calc R U . . .
C11 C 0.31938(13) 0.04268(6) 1.27779(11) 0.0137(2) Uani 1 1 d . . . . .
C12 C 0.31852(13) -0.01957(6) 1.22756(11) 0.0147(2) Uani 1 1 d . . . . .
H12 H 0.3422 -0.0558 1.2830 0.018 Uiso 1 1 calc R U . . .
C13 C 0.28314(13) -0.02834(5) 1.09721(11) 0.0135(2) Uani 1 1 d . . . . .
C14 C 0.23826(12) 0.02403(5) 1.01064(11) 0.0115(2) Uani 1 1 d . . . . .
C15 C 0.38288(18) 0.10814(7) 1.46329(13) 0.0287(3) Uani 1 1 d . . . . .
H15A H 0.4567 0.1316 1.4324 0.043 Uiso 1 1 calc R U . . .
H15B H 0.4174 0.1040 1.5563 0.043 Uiso 1 1 calc R U . . .
H15C H 0.2894 0.1320 1.4398 0.043 Uiso 1 1 calc R U . . .
C16 C 0.3294(2) -0.14164(6) 1.12956(13) 0.0287(3) Uani 1 1 d . . . . .
H16A H 0.4286 -0.1356 1.1872 0.043 Uiso 1 1 calc R U . . .
H16B H 0.3269 -0.1815 1.0803 0.043 Uiso 1 1 calc R U . . .
H16C H 0.2577 -0.1447 1.1795 0.043 Uiso 1 1 calc R U . . .
C17 C 0.01692(13) 0.22465(5) 0.72745(11) 0.0133(2) Uani 1 1 d . . . . .
C18 C -0.08771(14) 0.19769(6) 0.62431(12) 0.0171(2) Uani 1 1 d . . . . .
H18 H -0.0594 0.1661 0.5722 0.020 Uiso 1 1 calc R U . . .
C19 C -0.23380(15) 0.21735(6) 0.59826(12) 0.0199(2) Uani 1 1 d . . . . .
H19 H -0.3054 0.1987 0.5282 0.024 Uiso 1 1 calc R U . . .
C20 C -0.27752(14) 0.26398(6) 0.67301(13) 0.0186(2) Uani 1 1 d . . . . .
C21 C -0.17066(15) 0.29040(6) 0.77549(13) 0.0190(2) Uani 1 1 d . . . . .
H21 H -0.1986 0.3225 0.8268 0.023 Uiso 1 1 calc R U . . .
C22 C -0.02445(14) 0.27091(6) 0.80409(12) 0.0167(2) Uani 1 1 d . . . . .
H22 H 0.0468 0.2889 0.8751 0.020 Uiso 1 1 calc R U . . .
C23 C -0.43608(16) 0.28539(8) 0.64505(15) 0.0277(3) Uani 1 1 d . . . . .
H23A H -0.4415 0.3326 0.6356 0.042 Uiso 1 1 calc R U . . .
H23B H -0.4759 0.2725 0.7155 0.042 Uiso 1 1 calc R U . . .
H23C H -0.4940 0.2650 0.5659 0.042 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
S1 O4 1.4318(10) . ?
S1 O3 1.4357(9) . ?
S1 N1 1.6377(10) . ?
S1 C17 1.7598(12) . ?
N1 C8 1.4650(15) . ?
N1 C7 1.4685(14) . ?
O1 C11 1.3588(14) . ?
O1 C15 1.4224(16) . ?
O2 C13 1.3713(14) . ?
O2 C16 1.4245(15) . ?
C1 C14 1.5264(15) . ?
C1 C7 1.5397(15) . ?
C1 C2 1.5453(16) . ?
C1 C6 1.5453(16) . ?
C2 C3 1.5007(18) . ?
C3 C4 1.3664(19) . ?
C4 C5 1.4554(19) . ?
C5 C6 1.5166(17) . ?
C8 C9 1.5117(15) . ?
C9 C14 1.3960(15) . ?
C9 C10 1.3994(16) . ?
C10 C11 1.3832(16) . ?
C11 C12 1.3965(16) . ?
C12 C13 1.3802(16) . ?
C13 C14 1.4213(15) . ?
C17 C18 1.3919(17) . ?
C17 C22 1.3938(16) . ?
C18 C19 1.3875(18) . ?
C19 C20 1.3952(19) . ?
C20 C21 1.3936(19) . ?
C20 C23 1.5065(19) . ?
C21 C22 1.3859(18) . ?

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
O4 S1 O3 119.61(6) . . ?
O4 S1 N1 106.97(5) . . ?
O3 S1 N1 106.90(5) . . ?
O4 S1 C17 107.64(6) . . ?
O3 S1 C17 108.29(6) . . ?
N1 S1 C17 106.78(5) . . ?
C8 N1 C7 110.10(9) . . ?
C8 N1 S1 116.60(7) . . ?
C7 N1 S1 116.84(8) . . ?
C11 O1 C15 116.82(10) . . ?
C13 O2 C16 117.33(10) . . ?
C14 C1 C7 109.36(9) . . ?
C14 C1 C2 110.41(9) . . ?
C7 C1 C2 109.00(9) . . ?
C14 C1 C6 112.69(9) . . ?
C7 C1 C6 105.86(9) . . ?
C2 C1 C6 109.37(9) . . ?
C3 C2 C1 112.93(10) . . ?
C4 C3 C2 121.84(12) . . ?
C3 C4 C5 123.30(12) . . ?
C4 C5 C6 115.43(11) . . ?
C5 C6 C1 111.92(10) . . ?
N1 C7 C1 110.68(9) . . ?
N1 C8 C9 109.63(9) . . ?
C14 C9 C10 122.90(10) . . ?
C14 C9 C8 121.78(10) . . ?
C10 C9 C8 115.32(9) . . ?
C11 C10 C9 118.99(10) . . ?
O1 C11 C10 125.26(11) . . ?
O1 C11 C12 114.52(10) . . ?
C10 C11 C12 120.21(11) . . ?
C13 C12 C11 119.91(10) . . ?
O2 C13 C12 121.53(10) . . ?
O2 C13 C14 116.58(10) . . ?
C12 C13 C14 121.88(10) . . ?
C9 C14 C13 115.99(10) . . ?
C9 C14 C1 121.90(10) . . ?
C13 C14 C1 122.07(10) . . ?
C18 C17 C22 120.40(11) . . ?
C18 C17 S1 119.29(9) . . ?
C22 C17 S1 120.25(9) . . ?
C19 C18 C17 119.39(11) . . ?
C18 C19 C20 121.20(12) . . ?
C21 C20 C19 118.34(12) . . ?
C21 C20 C23 120.33(12) . . ?
C19 C20 C23 121.33(13) . . ?
C22 C21 C20 121.40(12) . . ?
C21 C22 C17 119.26(12) . . ?

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
O4 S1 N1 C8 176.01(8) . . . . ?
O3 S1 N1 C8 46.78(10) . . . . ?
C17 S1 N1 C8 -68.96(9) . . . . ?
O4 S1 N1 C7 -50.82(10) . . . . ?
O3 S1 N1 C7 179.95(8) . . . . ?
C17 S1 N1 C7 64.21(9) . . . . ?
C14 C1 C2 C3 171.69(10) . . . . ?
C7 C1 C2 C3 -68.16(12) . . . . ?
C6 C1 C2 C3 47.14(13) . . . . ?
C1 C2 C3 C4 -20.97(18) . . . . ?
C2 C3 C4 C5 2.2(2) . . . . ?
C3 C4 C5 C6 -11.62(18) . . . . ?
C4 C5 C6 C1 39.40(15) . . . . ?
C14 C1 C6 C5 179.88(10) . . . . ?
C7 C1 C6 C5 60.39(12) . . . . ?
C2 C1 C6 C5 -56.91(13) . . . . ?
C8 N1 C7 C1 -70.83(12) . . . . ?
S1 N1 C7 C1 153.15(8) . . . . ?
C14 C1 C7 N1 45.99(12) . . . . ?
C2 C1 C7 N1 -74.81(11) . . . . ?
C6 C1 C7 N1 167.64(9) . . . . ?
C7 N1 C8 C9 55.82(12) . . . . ?
S1 N1 C8 C9 -168.05(8) . . . . ?
N1 C8 C9 C14 -22.40(15) . . . . ?
N1 C8 C9 C10 158.67(10) . . . . ?
C14 C9 C10 C11 -1.13(17) . . . . ?
C8 C9 C10 C11 177.78(10) . . . . ?
C15 O1 C11 C10 -6.79(18) . . . . ?
C15 O1 C11 C12 171.95(12) . . . . ?
C9 C10 C11 O1 179.97(11) . . . . ?
C9 C10 C11 C12 1.29(17) . . . . ?
O1 C11 C12 C13 -177.64(11) . . . . ?
C10 C11 C12 C13 1.17(18) . . . . ?
C16 O2 C13 C12 5.34(18) . . . . ?
C16 O2 C13 C14 -176.30(12) . . . . ?
C11 C12 C13 O2 174.37(11) . . . . ?
C11 C12 C13 C14 -3.91(18) . . . . ?
C10 C9 C14 C13 -1.41(17) . . . . ?
C8 C9 C14 C13 179.74(10) . . . . ?
C10 C9 C14 C1 -179.23(10) . . . . ?
C8 C9 C14 C1 1.93(17) . . . . ?
O2 C13 C14 C9 -174.41(10) . . . . ?
C12 C13 C14 C9 3.95(17) . . . . ?
O2 C13 C14 C1 3.40(17) . . . . ?
C12 C13 C14 C1 -178.24(11) . . . . ?
C7 C1 C14 C9 -13.22(15) . . . . ?
C2 C1 C14 C9 106.71(12) . . . . ?
C6 C1 C14 C9 -130.66(11) . . . . ?
C7 C1 C14 C13 169.10(10) . . . . ?
C2 C1 C14 C13 -70.97(13) . . . . ?
C6 C1 C14 C13 51.66(14) . . . . ?
O4 S1 C17 C18 28.37(11) . . . . ?
O3 S1 C17 C18 159.00(10) . . . . ?
N1 S1 C17 C18 -86.20(10) . . . . ?
O4 S1 C17 C22 -154.36(10) . . . . ?
O3 S1 C17 C22 -23.73(11) . . . . ?
N1 S1 C17 C22 91.07(10) . . . . ?
C22 C17 C18 C19 0.08(18) . . . . ?
S1 C17 C18 C19 177.35(10) . . . . ?
C17 C18 C19 C20 0.46(19) . . . . ?
C18 C19 C20 C21 -0.25(19) . . . . ?
C18 C19 C20 C23 -179.94(12) . . . . ?
C19 C20 C21 C22 -0.51(19) . . . . ?
C23 C20 C21 C22 179.18(12) . . . . ?
C20 C21 C22 C17 1.04(19) . . . . ?
C18 C17 C22 C21 -0.82(18) . . . . ?
S1 C17 C22 C21 -178.06(9) . . . . ?

_refine_diff_density_max         0.428
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.084
_shelxl_version_number           2014-3
####################################################################### 
# 
# 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_mo_zrii7
_database_code_depnum_ccdc_archive 'CCDC 1530341'
_audit_update_record             
;
2017-01-30 deposited with the CCDC.
2017-02-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H27 N O5'
_chemical_formula_weight         397.45
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'

_symmetry_cell_setting           Monoclinic
_space_group_IT_number           14
_symmetry_space_group_name_H-M   P2(1)/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                   9.8767(14)
_cell_length_b                   23.638(3)
_cell_length_c                   8.6175(12)
_cell_angle_alpha                90
_cell_angle_beta                 102.363(4)
_cell_angle_gamma                90
_cell_volume                     1965.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9953
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      33.18

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.766
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_special_details           
; 
 It should be noted that the esd's of the cell dimensions are probably too low;
 they should be multiplied by a factor of 2 to 10
;
_diffrn_ambient_temperature      100(2)
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Microfocus source E025 IuS'
_diffrn_source_type              'Bruker APEX DUO'
_diffrn_source_power             50
_diffrn_source_current           0.6
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_radiation_monochromator  'Quazar MX Multilayer Optics'
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measurement_device_type  'APEX DUO Kappa 4-axis goniometer'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            59094
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.723
_diffrn_reflns_theta_max         33.188
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7505
_reflns_number_gt                6838
_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 v2011.4-0'
_computing_cell_refinement       'Bruker APEX2 v2011.4-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_structure_solution    Sir2011
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0572P)²+0.9498P] 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         7505
_refine_ls_number_parameters     267
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1284
_refine_ls_wR_factor_gt          0.1255
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_restrained_S_all      1.127
_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
N1 N 0.64925(9) 0.20083(3) 0.09737(10) 0.01431(15) Uani 1 1 d . . . . .
O1 O 1.19019(8) 0.19273(3) 0.43122(9) 0.01794(14) Uani 1 1 d . . . . .
O2 O 0.82442(8) 0.03088(3) 0.23642(9) 0.01781(14) Uani 1 1 d . . . . .
O3 O 0.80560(9) -0.00328(3) 0.47429(10) 0.02169(16) Uani 1 1 d . . . . .
O4 O 0.79256(8) 0.10930(4) 0.62097(9) 0.01841(15) Uani 1 1 d . . . . .
O5 O 0.56769(9) 0.08968(5) 0.60082(10) 0.02658(19) Uani 1 1 d . . . . .
C1 C 0.78734(10) 0.20489(4) 0.17375(11) 0.01329(15) Uani 1 1 d . . . . .
C2 C 0.88763(11) 0.24421(4) 0.15147(12) 0.01622(17) Uani 1 1 d . . . . .
H2 H 0.8654 0.2740 0.0764 0.019 Uiso 1 1 calc R U . . .
C3 C 1.01975(11) 0.23805(4) 0.24245(12) 0.01650(17) Uani 1 1 d . . . . .
H3 H 1.0895 0.2644 0.2308 0.020 Uiso 1 1 calc R U . . .
C4 C 1.05354(10) 0.19336(4) 0.35246(12) 0.01403(16) Uani 1 1 d . . . . .
C5 C 0.95487(10) 0.15439(4) 0.37565(11) 0.01271(15) Uani 1 1 d . . . . .
H5 H 0.9785 0.1243 0.4496 0.015 Uiso 1 1 calc R U . . .
C6 C 0.81823(10) 0.16077(4) 0.28604(11) 0.01149(15) Uani 1 1 d . . . . .
C7 C 0.69136(9) 0.13001(4) 0.27682(10) 0.01124(15) Uani 1 1 d . . . . .
C8 C 0.66703(9) 0.07756(4) 0.36767(11) 0.01192(15) Uani 1 1 d . . . . .
C9 C 0.52626(10) 0.05010(4) 0.29068(12) 0.01509(16) Uani 1 1 d . . . . .
H9A H 0.5364 0.0277 0.1968 0.018 Uiso 1 1 calc R U . . .
H9B H 0.4971 0.0242 0.3676 0.018 Uiso 1 1 calc R U . . .
C10 C 0.41610(10) 0.09559(4) 0.24024(11) 0.01385(16) Uani 1 1 d . . . . .
H10 H 0.4229 0.1212 0.3339 0.017 Uiso 1 1 calc R U . . .
C11 C 0.27042(10) 0.07264(4) 0.20505(12) 0.01691(17) Uani 1 1 d . . . . .
H11 H 0.2522 0.0382 0.2534 0.020 Uiso 1 1 calc R U . . .
C12 C 0.16609(11) 0.09910(5) 0.10829(12) 0.01779(18) Uani 1 1 d . . . . .
H12 H 0.0752 0.0841 0.0960 0.021 Uiso 1 1 calc R U . . .
C13 C 0.18629(11) 0.15157(5) 0.01814(12) 0.01831(18) Uani 1 1 d . . . . .
H13A H 0.1147 0.1796 0.0299 0.022 Uiso 1 1 calc R U . . .
H13B H 0.1727 0.1421 -0.0961 0.022 Uiso 1 1 calc R U . . .
C14 C 0.32996(10) 0.17834(4) 0.07401(12) 0.01706(17) Uani 1 1 d . . . . .
H14A H 0.3324 0.1997 0.1734 0.020 Uiso 1 1 calc R U . . .
H14B H 0.3472 0.2053 -0.0075 0.020 Uiso 1 1 calc R U . . .
C15 C 0.44552(10) 0.13298(4) 0.10354(11) 0.01307(15) Uani 1 1 d . . . . .
C16 C 0.59071(10) 0.15546(4) 0.16142(11) 0.01243(15) Uani 1 1 d . . . . .
C17 C 0.58521(12) 0.23929(5) -0.02934(14) 0.0216(2) Uani 1 1 d . . . . .
H17A H 0.5316 0.2680 0.0134 0.032 Uiso 1 1 calc R U . . .
H17B H 0.5235 0.2179 -0.1133 0.032 Uiso 1 1 calc R U . . .
H17C H 0.6575 0.2578 -0.0733 0.032 Uiso 1 1 calc R U . . .
C18 C 1.23171(11) 0.14856(5) 0.54351(13) 0.01884(18) Uani 1 1 d . . . . .
H18A H 1.1775 0.1507 0.6262 0.028 Uiso 1 1 calc R U . . .
H18B H 1.3304 0.1527 0.5920 0.028 Uiso 1 1 calc R U . . .
H18C H 1.2158 0.1119 0.4896 0.028 Uiso 1 1 calc R U . . .
C19 C 0.66748(10) 0.09227(4) 0.54176(11) 0.01430(16) Uani 1 1 d . . . . .
C20 C 0.80185(13) 0.12256(5) 0.78673(13) 0.0233(2) Uani 1 1 d . . . . .
H20A H 0.7352 0.1524 0.7958 0.035 Uiso 1 1 calc R U . . .
H20B H 0.8958 0.1355 0.8341 0.035 Uiso 1 1 calc R U . . .
H20C H 0.7808 0.0887 0.8427 0.035 Uiso 1 1 calc R U . . .
C21 C 0.77515(10) 0.03123(4) 0.36893(11) 0.01405(16) Uani 1 1 d . . . . .
C22 C 0.92366(12) -0.01342(5) 0.22841(14) 0.0218(2) Uani 1 1 d . . . . .
H22A H 1.0071 -0.0075 0.3117 0.033 Uiso 1 1 calc R U . . .
H22B H 0.9483 -0.0126 0.1242 0.033 Uiso 1 1 calc R U . . .
H22C H 0.8828 -0.0502 0.2440 0.033 Uiso 1 1 calc R U . . .
C23 C 0.44302(11) 0.09821(5) -0.04934(12) 0.01751(18) Uani 1 1 d . . . . .
H23A H 0.4483 0.1239 -0.1371 0.026 Uiso 1 1 calc R U . . .
H23B H 0.3568 0.0764 -0.0759 0.026 Uiso 1 1 calc R U . . .
H23C H 0.5224 0.0723 -0.0318 0.026 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 C1 1.3850(13) . ?
N1 C16 1.3877(12) . ?
N1 C17 1.4571(13) . ?
O1 C4 1.3748(12) . ?
O1 C18 1.4229(13) . ?
O2 C21 1.3338(12) . ?
O2 C22 1.4460(13) . ?
O3 C21 1.2098(12) . ?
O4 C19 1.3390(12) . ?
O4 C20 1.4461(13) . ?
O5 C19 1.2037(12) . ?
C1 C2 1.4012(13) . ?
C1 C6 1.4110(13) . ?
C2 C3 1.3786(15) . ?
C3 C4 1.4110(14) . ?
C4 C5 1.3862(13) . ?
C5 C6 1.4121(13) . ?
C6 C7 1.4361(12) . ?
C7 C16 1.3841(13) . ?
C7 C8 1.5127(12) . ?
C8 C21 1.5279(13) . ?
C8 C19 1.5390(13) . ?
C8 C9 1.5490(13) . ?
C9 C10 1.5252(14) . ?
C10 C11 1.5066(14) . ?
C10 C15 1.5491(13) . ?
C11 C12 1.3343(14) . ?
C12 C13 1.4994(15) . ?
C13 C14 1.5340(15) . ?
C14 C15 1.5469(14) . ?
C15 C16 1.5104(13) . ?
C15 C23 1.5485(14) . ?

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
C1 N1 C16 108.44(8) . . ?
C1 N1 C17 122.56(8) . . ?
C16 N1 C17 129.00(9) . . ?
C4 O1 C18 116.95(8) . . ?
C21 O2 C22 114.88(8) . . ?
C19 O4 C20 115.16(8) . . ?
N1 C1 C2 129.34(9) . . ?
N1 C1 C6 108.72(8) . . ?
C2 C1 C6 121.93(9) . . ?
C3 C2 C1 117.57(9) . . ?
C2 C3 C4 121.34(9) . . ?
O1 C4 C5 124.60(9) . . ?
O1 C4 C3 113.94(8) . . ?
C5 C4 C3 121.46(9) . . ?
C4 C5 C6 117.99(8) . . ?
C1 C6 C5 119.67(8) . . ?
C1 C6 C7 106.16(8) . . ?
C5 C6 C7 134.15(8) . . ?
C16 C7 C6 107.67(8) . . ?
C16 C7 C8 123.98(8) . . ?
C6 C7 C8 128.29(8) . . ?
C7 C8 C21 113.76(7) . . ?
C7 C8 C19 110.59(7) . . ?
C21 C8 C19 107.39(7) . . ?
C7 C8 C9 110.43(7) . . ?
C21 C8 C9 105.34(7) . . ?
C19 C8 C9 109.10(7) . . ?
C10 C9 C8 110.29(8) . . ?
C11 C10 C9 113.31(8) . . ?
C11 C10 C15 112.27(8) . . ?
C9 C10 C15 112.36(8) . . ?
C12 C11 C10 122.24(9) . . ?
C11 C12 C13 122.75(9) . . ?
C12 C13 C14 113.29(8) . . ?
C13 C14 C15 111.47(8) . . ?
C16 C15 C14 115.17(8) . . ?
C16 C15 C23 107.98(8) . . ?
C14 C15 C23 110.55(8) . . ?
C16 C15 C10 105.61(7) . . ?
C14 C15 C10 105.58(7) . . ?
C23 C15 C10 111.89(8) . . ?
C7 C16 N1 108.99(8) . . ?
C7 C16 C15 124.70(8) . . ?
N1 C16 C15 125.98(8) . . ?
O5 C19 O4 123.32(9) . . ?
O5 C19 C8 124.67(9) . . ?
O4 C19 C8 112.00(8) . . ?
O3 C21 O2 124.11(9) . . ?
O3 C21 C8 123.35(9) . . ?
O2 C21 C8 112.39(8) . . ?

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
C16 N1 C1 C2 -179.11(10) . . . . ?
C17 N1 C1 C2 1.55(16) . . . . ?
C16 N1 C1 C6 1.19(10) . . . . ?
C17 N1 C1 C6 -178.15(9) . . . . ?
N1 C1 C2 C3 -178.90(9) . . . . ?
C6 C1 C2 C3 0.77(14) . . . . ?
C1 C2 C3 C4 0.88(15) . . . . ?
C18 O1 C4 C5 0.30(14) . . . . ?
C18 O1 C4 C3 -179.68(9) . . . . ?
C2 C3 C4 O1 178.84(9) . . . . ?
C2 C3 C4 C5 -1.14(15) . . . . ?
O1 C4 C5 C6 179.75(9) . . . . ?
C3 C4 C5 C6 -0.27(14) . . . . ?
N1 C1 C6 C5 177.55(8) . . . . ?
C2 C1 C6 C5 -2.18(14) . . . . ?
N1 C1 C6 C7 -1.04(10) . . . . ?
C2 C1 C6 C7 179.23(9) . . . . ?
C4 C5 C6 C1 1.87(13) . . . . ?
C4 C5 C6 C7 179.99(9) . . . . ?
C1 C6 C7 C16 0.51(10) . . . . ?
C5 C6 C7 C16 -177.79(10) . . . . ?
C1 C6 C7 C8 177.88(9) . . . . ?
C5 C6 C7 C8 -0.42(17) . . . . ?
C16 C7 C8 C21 129.70(9) . . . . ?
C6 C7 C8 C21 -47.28(12) . . . . ?
C16 C7 C8 C19 -109.36(10) . . . . ?
C6 C7 C8 C19 73.66(11) . . . . ?
C16 C7 C8 C9 11.50(12) . . . . ?
C6 C7 C8 C9 -165.47(9) . . . . ?
C7 C8 C9 C10 -40.96(10) . . . . ?
C21 C8 C9 C10 -164.20(8) . . . . ?
C19 C8 C9 C10 80.78(9) . . . . ?
C8 C9 C10 C11 -164.69(8) . . . . ?
C8 C9 C10 C15 66.75(10) . . . . ?
C9 C10 C11 C12 -155.31(10) . . . . ?
C15 C10 C11 C12 -26.70(13) . . . . ?
C10 C11 C12 C13 4.21(16) . . . . ?
C11 C12 C13 C14 -12.11(14) . . . . ?
C12 C13 C14 C15 42.71(11) . . . . ?
C13 C14 C15 C16 -179.11(8) . . . . ?
C13 C14 C15 C23 58.16(10) . . . . ?
C13 C14 C15 C10 -63.03(10) . . . . ?
C11 C10 C15 C16 176.39(8) . . . . ?
C9 C10 C15 C16 -54.50(10) . . . . ?
C11 C10 C15 C14 53.95(10) . . . . ?
C9 C10 C15 C14 -176.94(8) . . . . ?
C11 C10 C15 C23 -66.37(10) . . . . ?
C9 C10 C15 C23 62.74(10) . . . . ?
C6 C7 C16 N1 0.21(10) . . . . ?
C8 C7 C16 N1 -177.31(8) . . . . ?
C6 C7 C16 C15 174.01(8) . . . . ?
C8 C7 C16 C15 -3.50(14) . . . . ?
C1 N1 C16 C7 -0.86(11) . . . . ?
C17 N1 C16 C7 178.42(10) . . . . ?
C1 N1 C16 C15 -174.57(8) . . . . ?
C17 N1 C16 C15 4.72(16) . . . . ?
C14 C15 C16 C7 139.83(9) . . . . ?
C23 C15 C16 C7 -96.09(10) . . . . ?
C10 C15 C16 C7 23.75(12) . . . . ?
C14 C15 C16 N1 -47.42(13) . . . . ?
C23 C15 C16 N1 76.66(11) . . . . ?
C10 C15 C16 N1 -163.49(9) . . . . ?
C20 O4 C19 O5 2.32(15) . . . . ?
C20 O4 C19 C8 -178.55(9) . . . . ?
C7 C8 C19 O5 112.58(11) . . . . ?
C21 C8 C19 O5 -122.77(11) . . . . ?
C9 C8 C19 O5 -9.07(14) . . . . ?
C7 C8 C19 O4 -66.53(10) . . . . ?
C21 C8 C19 O4 58.12(10) . . . . ?
C9 C8 C19 O4 171.82(8) . . . . ?
C22 O2 C21 O3 -2.27(14) . . . . ?
C22 O2 C21 C8 -177.90(8) . . . . ?
C7 C8 C21 O3 152.50(9) . . . . ?
C19 C8 C21 O3 29.79(12) . . . . ?
C9 C8 C21 O3 -86.41(11) . . . . ?
C7 C8 C21 O2 -31.83(11) . . . . ?
C19 C8 C21 O2 -154.55(8) . . . . ?
C9 C8 C21 O2 89.26(9) . . . . ?

_refine_diff_density_max         0.629
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.062
_shelxl_version_number           2014-3
