# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1851667'
_audit_update_record             
;
2018-06-26 deposited with the CCDC.
2018-08-06 downloaded from the CCDC.
;
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H19 N O6'
_chemical_formula_sum            'C18 H19 N O6'
_chemical_formula_weight         345.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   9.23510(17)
_cell_length_b                   14.6347(3)
_cell_length_c                   25.4336(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.9605(7)
_cell_angle_gamma                90
_cell_volume                     3412.08(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    30671
_cell_measurement_theta_min      3.50
_cell_measurement_theta_max      68.22

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_F_000             1456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.400
_exptl_absorpt_coefficient_mu    0.851
_shelx_estimated_absorpt_T_min   0.676
_shelx_estimated_absorpt_T_max   0.727
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  0.579
_exptl_absorpt_correction_T_max  0.711

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating anode'
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            31128
_diffrn_reflns_av_unetI/netI     0.0110
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.501
_diffrn_reflns_theta_max         68.224
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3120
_reflns_number_gt                2990
_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       'RAPID AUTO (Rigaku, 2004)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0494P)²+2.1816P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00187(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3120
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.0943
_refine_ls_wR_factor_gt          0.0934
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.004
_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
O1 O 1.11078(9) 0.42999(6) 0.39060(3) 0.0287(2) Uani 1 1 d . . . . .
O2 O 0.72492(11) 0.57568(7) 0.33233(4) 0.0427(3) Uani 1 1 d . . . . .
O3 O 0.60599(9) 0.46610(6) 0.37083(4) 0.0318(2) Uani 1 1 d . . . . .
O4 O 0.74700(11) 0.51110(6) 0.48259(4) 0.0390(3) Uani 1 1 d . . . . .
O5 O 0.69566(12) 0.36569(7) 0.49942(4) 0.0417(3) Uani 1 1 d . . . . .
O6 O 1.00558(10) 0.28518(6) 0.37408(3) 0.0329(2) Uani 1 1 d . . . . .
N1 N 1.22466(15) 0.87014(8) 0.25963(5) 0.0454(3) Uani 1 1 d . . . . .
C1 C 0.99227(13) 0.48415(8) 0.37655(5) 0.0257(3) Uani 1 1 d . . . . .
C2 C 0.85823(13) 0.46501(8) 0.38923(5) 0.0265(3) Uani 1 1 d . . . . .
C3 C 0.83523(13) 0.39140(8) 0.42923(5) 0.0268(3) Uani 1 1 d . . . . .
H3 H 0.7773 0.3402 0.4112 0.032 Uiso 1 1 calc R U . . .
C4 C 0.98315(14) 0.35501(9) 0.45523(5) 0.0293(3) Uani 1 1 d . . . . .
H4A H 1.0275 0.3993 0.4819 0.035 Uiso 1 1 calc R U . . .
H4B H 0.9691 0.2964 0.4734 0.035 Uiso 1 1 calc R U . . .
C5 C 1.08288(14) 0.34096(8) 0.41278(5) 0.0293(3) Uani 1 1 d . . . . .
C6 C 0.72820(14) 0.51081(9) 0.36153(5) 0.0287(3) Uani 1 1 d . . . . .
C7 C 0.47291(15) 0.50101(11) 0.34249(6) 0.0389(3) Uani 1 1 d . . . . .
H7A H 0.3894 0.4685 0.3540 0.047 Uiso 1 1 calc R U . . .
H7B H 0.4743 0.4919 0.3044 0.047 Uiso 1 1 calc R U . . .
H7C H 0.4645 0.5664 0.3499 0.047 Uiso 1 1 calc R U . . .
C8 C 0.75414(13) 0.43118(9) 0.47239(5) 0.0284(3) Uani 1 1 d . . . . .
C9 C 0.62788(18) 0.39641(11) 0.54486(6) 0.0459(4) Uani 1 1 d . . . . .
H9A H 0.6169 0.3445 0.5684 0.055 Uiso 1 1 calc R U . . .
H9B H 0.5317 0.4223 0.5328 0.055 Uiso 1 1 calc R U . . .
H9C H 0.6893 0.4432 0.5640 0.055 Uiso 1 1 calc R U . . .
C10 C 1.23285(15) 0.30476(10) 0.43312(6) 0.0379(3) Uani 1 1 d . . . . .
H10A H 1.2757 0.3425 0.4628 0.045 Uiso 1 1 calc R U . . .
H10B H 1.2954 0.3068 0.4046 0.045 Uiso 1 1 calc R U . . .
H10C H 1.2245 0.2415 0.4451 0.045 Uiso 1 1 calc R U . . .
C11 C 1.06693(18) 0.27540(10) 0.32537(6) 0.0413(4) Uani 1 1 d . . . . .
H11A H 1.0106 0.2302 0.3030 0.050 Uiso 1 1 calc R U . . .
H11B H 1.1684 0.2549 0.3328 0.050 Uiso 1 1 calc R U . . .
H11C H 1.0638 0.3343 0.3070 0.050 Uiso 1 1 calc R U . . .
C12 C 1.03848(13) 0.56671(8) 0.34878(5) 0.0256(3) Uani 1 1 d . . . . .
C13 C 1.12133(13) 0.55951(8) 0.30673(5) 0.0268(3) Uani 1 1 d . . . . .
H13 H 1.1439 0.5010 0.2938 0.032 Uiso 1 1 calc R U . . .
C14 C 1.17102(13) 0.63755(9) 0.28364(5) 0.0288(3) Uani 1 1 d . . . . .
H14 H 1.2265 0.6327 0.2547 0.035 Uiso 1 1 calc R U . . .
C15 C 1.13902(13) 0.72306(9) 0.30325(5) 0.0282(3) Uani 1 1 d . . . . .
C16 C 1.05765(14) 0.73078(9) 0.34586(5) 0.0317(3) Uani 1 1 d . . . . .
H16 H 1.0367 0.7893 0.3593 0.038 Uiso 1 1 calc R U . . .
C17 C 1.00803(14) 0.65289(9) 0.36832(5) 0.0310(3) Uani 1 1 d . . . . .
H17 H 0.9527 0.6579 0.3973 0.037 Uiso 1 1 calc R U . . .
C18 C 1.18740(15) 0.80492(9) 0.27898(5) 0.0332(3) 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 C1 1.3634(14) . ?
O1 C5 1.4552(15) . ?
O2 C6 1.2034(16) . ?
O3 C6 1.3501(15) . ?
O3 C7 1.4409(16) . ?
O4 C8 1.2016(16) . ?
O5 C8 1.3315(16) . ?
O5 C9 1.4508(17) . ?
O6 C5 1.4051(16) . ?
O6 C11 1.4305(16) . ?
N1 C18 1.1457(18) . ?
C1 C2 1.3459(18) . ?
C1 C12 1.4879(17) . ?
C2 C6 1.4773(17) . ?
C2 C3 1.5144(16) . ?
C3 C8 1.5178(17) . ?
C3 C4 1.5388(17) . ?
C3 H3 1.0000 . ?
C4 C5 1.5158(17) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C10 1.5143(18) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.3925(17) . ?
C12 C17 1.3964(17) . ?
C13 C14 1.3874(17) . ?
C13 H13 0.9500 . ?
C14 C15 1.3919(18) . ?
C14 H14 0.9500 . ?
C15 C16 1.3963(18) . ?
C15 C18 1.4432(17) . ?
C16 C17 1.3781(18) . ?
C16 H16 0.9500 . ?
C17 H17 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
C1 O1 C5 116.61(9) . . ?
C6 O3 C7 114.89(10) . . ?
C8 O5 C9 115.43(11) . . ?
C5 O6 C11 116.35(11) . . ?
C2 C1 O1 123.27(11) . . ?
C2 C1 C12 127.43(11) . . ?
O1 C1 C12 109.22(10) . . ?
C1 C2 C6 120.62(11) . . ?
C1 C2 C3 121.13(11) . . ?
C6 C2 C3 118.10(11) . . ?
C2 C3 C8 109.56(10) . . ?
C2 C3 C4 110.21(10) . . ?
C8 C3 C4 108.18(10) . . ?
C2 C3 H3 109.6 . . ?
C8 C3 H3 109.6 . . ?
C4 C3 H3 109.6 . . ?
C5 C4 C3 108.98(10) . . ?
C5 C4 H4A 109.9 . . ?
C3 C4 H4A 109.9 . . ?
C5 C4 H4B 109.9 . . ?
C3 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
O6 C5 O1 110.33(10) . . ?
O6 C5 C10 113.71(11) . . ?
O1 C5 C10 104.37(10) . . ?
O6 C5 C4 106.07(10) . . ?
O1 C5 C4 107.83(10) . . ?
C10 C5 C4 114.43(11) . . ?
O2 C6 O3 122.10(12) . . ?
O2 C6 C2 127.62(12) . . ?
O3 C6 C2 110.18(10) . . ?
O3 C7 H7A 109.5 . . ?
O3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O4 C8 O5 123.57(12) . . ?
O4 C8 C3 125.04(11) . . ?
O5 C8 C3 111.34(10) . . ?
O5 C9 H9A 109.5 . . ?
O5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O6 C11 H11A 109.5 . . ?
O6 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O6 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C17 119.65(11) . . ?
C13 C12 C1 121.27(11) . . ?
C17 C12 C1 118.87(11) . . ?
C14 C13 C12 120.23(11) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 119.53(11) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C16 120.56(11) . . ?
C14 C15 C18 120.20(11) . . ?
C16 C15 C18 119.23(12) . . ?
C17 C16 C15 119.47(12) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C12 120.54(11) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
N1 C18 C15 179.44(16) . . ?

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
C5 O1 C1 C2 10.02(17) . . . . ?
C5 O1 C1 C12 -173.10(10) . . . . ?
O1 C1 C2 C6 -163.41(11) . . . . ?
C12 C1 C2 C6 20.30(19) . . . . ?
O1 C1 C2 C3 12.11(19) . . . . ?
C12 C1 C2 C3 -164.18(11) . . . . ?
C1 C2 C3 C8 125.57(12) . . . . ?
C6 C2 C3 C8 -58.80(14) . . . . ?
C1 C2 C3 C4 6.64(16) . . . . ?
C6 C2 C3 C4 -177.73(10) . . . . ?
C2 C3 C4 C5 -43.73(13) . . . . ?
C8 C3 C4 C5 -163.49(10) . . . . ?
C11 O6 C5 O1 52.84(14) . . . . ?
C11 O6 C5 C10 -64.03(14) . . . . ?
C11 O6 C5 C4 169.35(10) . . . . ?
C1 O1 C5 O6 67.19(13) . . . . ?
C1 O1 C5 C10 -170.29(10) . . . . ?
C1 O1 C5 C4 -48.23(13) . . . . ?
C3 C4 C5 O6 -53.61(12) . . . . ?
C3 C4 C5 O1 64.58(13) . . . . ?
C3 C4 C5 C10 -179.80(11) . . . . ?
C7 O3 C6 O2 1.07(18) . . . . ?
C7 O3 C6 C2 -175.62(10) . . . . ?
C1 C2 C6 O2 -11.6(2) . . . . ?
C3 C2 C6 O2 172.78(13) . . . . ?
C1 C2 C6 O3 164.89(11) . . . . ?
C3 C2 C6 O3 -10.76(15) . . . . ?
C9 O5 C8 O4 -3.31(19) . . . . ?
C9 O5 C8 C3 174.25(12) . . . . ?
C2 C3 C8 O4 -20.24(18) . . . . ?
C4 C3 C8 O4 99.93(15) . . . . ?
C2 C3 C8 O5 162.23(11) . . . . ?
C4 C3 C8 O5 -77.60(13) . . . . ?
C2 C1 C12 C13 -132.64(14) . . . . ?
O1 C1 C12 C13 50.64(15) . . . . ?
C2 C1 C12 C17 52.69(18) . . . . ?
O1 C1 C12 C17 -124.02(12) . . . . ?
C17 C12 C13 C14 -1.26(18) . . . . ?
C1 C12 C13 C14 -175.88(11) . . . . ?
C12 C13 C14 C15 0.81(18) . . . . ?
C13 C14 C15 C16 0.05(18) . . . . ?
C13 C14 C15 C18 -178.75(12) . . . . ?
C14 C15 C16 C17 -0.44(19) . . . . ?
C18 C15 C16 C17 178.37(12) . . . . ?
C15 C16 C17 C12 0.0(2) . . . . ?
C13 C12 C17 C16 0.87(19) . . . . ?
C1 C12 C17 C16 175.62(12) . . . . ?

_refine_diff_density_max         0.253
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.044

_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_I_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1851669'
_audit_update_record             
;
2018-06-26 deposited with the CCDC.
2018-08-06 downloaded from the CCDC.
;
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H19 Br O6'
_chemical_formula_sum            'C17 H19 Br O6'
_chemical_formula_weight         399.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   5.15537(9)
_cell_length_b                   43.3613(8)
_cell_length_c                   8.36326(15)
_cell_angle_alpha                90
_cell_angle_beta                 111.7414(7)
_cell_angle_gamma                90
_cell_volume                     1736.56(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    188(2)
_cell_measurement_reflns_used    26431
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      68.25

_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    3.493
_shelx_estimated_absorpt_T_min   0.228
_shelx_estimated_absorpt_T_max   0.845
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  0.280
_exptl_absorpt_correction_T_max  0.840

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      188(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating anode'
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            29569
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -52
_diffrn_reflns_limit_k_max       52
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.078
_diffrn_reflns_theta_max         68.250
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3161
_reflns_number_gt                2936
_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       'RAPID AUTO (Rigaku, 2004)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0480P)²+0.7299P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3161
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0868
_refine_ls_wR_factor_gt          0.0856
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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
Br1 Br -0.10152(6) 0.23986(2) 1.10417(3) 0.05139(12) Uani 1 1 d . . . . .
O1 O 0.5617(3) 0.37572(3) 1.16917(16) 0.0320(3) Uani 1 1 d . . . . .
O2 O 0.1390(3) 0.37544(4) 0.56160(19) 0.0442(4) Uani 1 1 d . . . . .
O3 O -0.0989(3) 0.35486(3) 0.71186(18) 0.0386(3) Uani 1 1 d . . . . .
O4 O 0.0247(3) 0.43495(3) 0.7659(2) 0.0410(3) Uani 1 1 d . . . . .
O5 O 0.4065(3) 0.46445(3) 0.84344(19) 0.0389(3) Uani 1 1 d . . . . .
O6 O 0.4992(3) 0.42838(3) 1.19906(17) 0.0318(3) Uani 1 1 d . . . . .
C1 C 0.3782(4) 0.36553(4) 1.0141(2) 0.0286(4) Uani 1 1 d . . . . .
C2 C 0.3222(4) 0.38082(4) 0.8651(2) 0.0286(4) Uani 1 1 d . . . . .
C3 C 0.4756(4) 0.41009(4) 0.8574(2) 0.0294(4) Uani 1 1 d . . . . .
H3 H 0.5368 0.4081 0.7575 0.035 Uiso 1 1 calc R U . . .
C4 C 0.7390(4) 0.41330(5) 1.0192(3) 0.0330(4) Uani 1 1 d . . . . .
H4A H 0.8842 0.3990 1.0118 0.040 Uiso 1 1 calc R U . . .
H4B H 0.8117 0.4346 1.0266 0.040 Uiso 1 1 calc R U . . .
C5 C 0.6803(4) 0.40618(4) 1.1786(2) 0.0310(4) Uani 1 1 d . . . . .
H5 H 0.8599 0.4070 1.2804 0.037 Uiso 1 1 calc R U . . .
C6 C 0.1173(4) 0.37017(4) 0.6978(2) 0.0306(4) Uani 1 1 d . . . . .
C7 C -0.2851(5) 0.34014(5) 0.5573(3) 0.0463(6) Uani 1 1 d . . . . .
H7A H -0.1909 0.3224 0.5299 0.056 Uiso 1 1 calc R U . . .
H7B H -0.3379 0.3549 0.4618 0.056 Uiso 1 1 calc R U . . .
H7C H -0.4529 0.3331 0.5752 0.056 Uiso 1 1 calc R U . . .
C8 C 0.2741(4) 0.43720(4) 0.8196(2) 0.0311(4) Uani 1 1 d . . . . .
C9 C 0.2238(6) 0.49095(5) 0.8036(4) 0.0503(6) Uani 1 1 d . . . . .
H9A H 0.1047 0.4906 0.6811 0.060 Uiso 1 1 calc R U . . .
H9B H 0.3360 0.5099 0.8297 0.060 Uiso 1 1 calc R U . . .
H9C H 0.1067 0.4903 0.8729 0.060 Uiso 1 1 calc R U . . .
C10 C 0.4728(5) 0.42672(5) 1.3639(3) 0.0416(5) Uani 1 1 d . . . . .
H10A H 0.6599 0.4255 1.4565 0.050 Uiso 1 1 calc R U . . .
H10B H 0.3660 0.4081 1.3699 0.050 Uiso 1 1 calc R U . . .
C11 C 0.3234(6) 0.45510(6) 1.3866(3) 0.0512(6) Uani 1 1 d . . . . .
H11A H 0.4345 0.4734 1.3856 0.061 Uiso 1 1 calc R U . . .
H11B H 0.2972 0.4540 1.4967 0.061 Uiso 1 1 calc R U . . .
H11C H 0.1409 0.4565 1.2924 0.061 Uiso 1 1 calc R U . . .
C12 C 0.2640(4) 0.33511(4) 1.0373(2) 0.0293(4) Uani 1 1 d . . . . .
C13 C 0.1334(4) 0.33183(4) 1.1547(2) 0.0324(4) Uani 1 1 d . . . . .
H13 H 0.1199 0.3490 1.2215 0.039 Uiso 1 1 calc R U . . .
C14 C 0.0222(5) 0.30362(5) 1.1753(3) 0.0357(4) Uani 1 1 d . . . . .
H14 H -0.0709 0.3014 1.2537 0.043 Uiso 1 1 calc R U . . .
C15 C 0.0497(5) 0.27879(4) 1.0793(3) 0.0361(5) Uani 1 1 d . . . . .
C16 C 0.1852(5) 0.28120(5) 0.9656(3) 0.0400(5) Uani 1 1 d . . . . .
H16 H 0.2046 0.2637 0.9023 0.048 Uiso 1 1 calc R U . . .
C17 C 0.2925(5) 0.30946(5) 0.9453(3) 0.0373(5) Uani 1 1 d . . . . .
H17 H 0.3869 0.3114 0.8674 0.045 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
Br1 C15 1.903(2) . ?
O1 C1 1.365(2) . ?
O1 C5 1.445(2) . ?
O2 C6 1.206(2) . ?
O3 C6 1.339(3) . ?
O3 C7 1.442(3) . ?
O4 C8 1.198(3) . ?
O5 C8 1.342(2) . ?
O5 C9 1.444(3) . ?
O6 C5 1.395(2) . ?
O6 C10 1.436(2) . ?
C1 C2 1.345(3) . ?
C1 C12 1.487(3) . ?
C2 C6 1.481(3) . ?
C2 C3 1.509(3) . ?
C3 C8 1.522(3) . ?
C3 C4 1.528(3) . ?
C3 H3 1.0000 . ?
C4 C5 1.504(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5 1.0000 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.501(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.388(3) . ?
C12 C17 1.391(3) . ?
C13 C14 1.388(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.381(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.376(3) . ?
C16 C17 1.381(3) . ?
C16 H16 0.9500 . ?
C17 H17 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
C1 O1 C5 118.54(14) . . ?
C6 O3 C7 116.08(17) . . ?
C8 O5 C9 114.43(18) . . ?
C5 O6 C10 112.90(15) . . ?
C2 C1 O1 123.79(17) . . ?
C2 C1 C12 126.81(18) . . ?
O1 C1 C12 109.37(15) . . ?
C1 C2 C6 123.71(18) . . ?
C1 C2 C3 121.19(17) . . ?
C6 C2 C3 115.08(16) . . ?
C2 C3 C8 109.29(16) . . ?
C2 C3 C4 110.30(16) . . ?
C8 C3 C4 115.33(16) . . ?
C2 C3 H3 107.2 . . ?
C8 C3 H3 107.2 . . ?
C4 C3 H3 107.2 . . ?
C5 C4 C3 111.19(16) . . ?
C5 C4 H4A 109.4 . . ?
C3 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
C3 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
O6 C5 O1 110.38(16) . . ?
O6 C5 C4 109.30(15) . . ?
O1 C5 C4 111.07(16) . . ?
O6 C5 H5 108.7 . . ?
O1 C5 H5 108.7 . . ?
C4 C5 H5 108.7 . . ?
O2 C6 O3 123.22(18) . . ?
O2 C6 C2 123.36(18) . . ?
O3 C6 C2 113.39(16) . . ?
O3 C7 H7A 109.5 . . ?
O3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O4 C8 O5 122.93(18) . . ?
O4 C8 C3 124.72(18) . . ?
O5 C8 C3 112.24(17) . . ?
O5 C9 H9A 109.5 . . ?
O5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O6 C10 C11 108.43(18) . . ?
O6 C10 H10A 110.0 . . ?
C11 C10 H10A 110.0 . . ?
O6 C10 H10B 110.0 . . ?
C11 C10 H10B 110.0 . . ?
H10A C10 H10B 108.4 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C17 119.19(18) . . ?
C13 C12 C1 120.20(17) . . ?
C17 C12 C1 120.59(18) . . ?
C12 C13 C14 120.59(18) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 118.58(19) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C16 C15 C14 122.01(19) . . ?
C16 C15 Br1 118.44(15) . . ?
C14 C15 Br1 119.55(16) . . ?
C15 C16 C17 118.77(19) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 H16 120.6 . . ?
C16 C17 C12 120.8(2) . . ?
C16 C17 H17 119.6 . . ?
C12 C17 H17 119.6 . . ?

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
C5 O1 C1 C2 7.1(3) . . . . ?
C5 O1 C1 C12 -174.95(15) . . . . ?
O1 C1 C2 C6 -178.23(17) . . . . ?
C12 C1 C2 C6 4.2(3) . . . . ?
O1 C1 C2 C3 3.9(3) . . . . ?
C12 C1 C2 C3 -173.69(18) . . . . ?
C1 C2 C3 C8 -111.6(2) . . . . ?
C6 C2 C3 C8 70.3(2) . . . . ?
C1 C2 C3 C4 16.2(3) . . . . ?
C6 C2 C3 C4 -161.92(17) . . . . ?
C2 C3 C4 C5 -45.2(2) . . . . ?
C8 C3 C4 C5 79.2(2) . . . . ?
C10 O6 C5 O1 68.4(2) . . . . ?
C10 O6 C5 C4 -169.14(16) . . . . ?
C1 O1 C5 O6 84.0(2) . . . . ?
C1 O1 C5 C4 -37.4(2) . . . . ?
C3 C4 C5 O6 -65.6(2) . . . . ?
C3 C4 C5 O1 56.4(2) . . . . ?
C7 O3 C6 O2 10.3(3) . . . . ?
C7 O3 C6 C2 -171.56(17) . . . . ?
C1 C2 C6 O2 -149.6(2) . . . . ?
C3 C2 C6 O2 28.4(3) . . . . ?
C1 C2 C6 O3 32.2(3) . . . . ?
C3 C2 C6 O3 -149.77(17) . . . . ?
C9 O5 C8 O4 1.7(3) . . . . ?
C9 O5 C8 C3 177.97(17) . . . . ?
C2 C3 C8 O4 -15.7(3) . . . . ?
C4 C3 C8 O4 -140.6(2) . . . . ?
C2 C3 C8 O5 168.09(16) . . . . ?
C4 C3 C8 O5 43.2(2) . . . . ?
C5 O6 C10 C11 168.56(18) . . . . ?
C2 C1 C12 C13 -126.4(2) . . . . ?
O1 C1 C12 C13 55.8(2) . . . . ?
C2 C1 C12 C17 55.2(3) . . . . ?
O1 C1 C12 C17 -122.6(2) . . . . ?
C17 C12 C13 C14 -2.6(3) . . . . ?
C1 C12 C13 C14 178.98(18) . . . . ?
C12 C13 C14 C15 1.4(3) . . . . ?
C13 C14 C15 C16 0.5(3) . . . . ?
C13 C14 C15 Br1 -179.82(15) . . . . ?
C14 C15 C16 C17 -1.1(3) . . . . ?
Br1 C15 C16 C17 179.22(17) . . . . ?
C15 C16 C17 C12 -0.2(3) . . . . ?
C13 C12 C17 C16 2.0(3) . . . . ?
C1 C12 C17 C16 -179.6(2) . . . . ?

_refine_diff_density_max         0.351
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.065

_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_I_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1851668'
_audit_update_record             
;
2018-06-26 deposited with the CCDC.
2018-08-06 downloaded from the CCDC.
;
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H19 N O6'
_chemical_formula_sum            'C18 H19 N O6'
_chemical_formula_weight         345.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   9.59148(17)
_cell_length_b                   8.88839(16)
_cell_length_c                   20.6593(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.3754(7)
_cell_angle_gamma                90
_cell_volume                     1753.52(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    30667
_cell_measurement_theta_min      4.30
_cell_measurement_theta_max      68.23

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.828
_shelx_estimated_absorpt_T_min   0.659
_shelx_estimated_absorpt_T_max   0.852
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  0.606
_exptl_absorpt_correction_T_max  0.847

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating anode'
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            31757
_diffrn_reflns_av_unetI/netI     0.0108
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.299
_diffrn_reflns_theta_max         68.232
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3209
_reflns_number_gt                3075
_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       'RAPID AUTO (Rigaku, 2004)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0515P)²+0.4800P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0092(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3209
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0948
_refine_ls_wR_factor_gt          0.0940
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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
O1 O -0.01505(8) 0.61021(9) 0.66169(4) 0.0315(2) Uani 1 1 d . . . . .
O2 O 0.37142(9) 0.28232(11) 0.66234(5) 0.0464(3) Uani 1 1 d . . . . .
O3 O 0.26594(9) 0.35837(10) 0.56653(4) 0.0389(2) Uani 1 1 d . . . . .
O4 O 0.02076(10) 0.13327(10) 0.76868(4) 0.0441(3) Uani 1 1 d . . . . .
O5 O 0.06742(9) 0.12807(9) 0.66468(4) 0.0369(2) Uani 1 1 d . . . . .
O6 O -0.15467(8) 0.40581(9) 0.68433(4) 0.0338(2) Uani 1 1 d . . . . .
N1 N 0.32818(14) 1.02733(16) 0.41253(6) 0.0545(3) Uani 1 1 d . . . . .
C1 C 0.09616(11) 0.54381(12) 0.63702(5) 0.0271(2) Uani 1 1 d . . . . .
C2 C 0.15886(11) 0.41780(12) 0.66126(6) 0.0282(3) Uani 1 1 d . . . . .
C3 C 0.12363(12) 0.35277(13) 0.72515(6) 0.0309(3) Uani 1 1 d . . . . .
H3 H 0.2145 0.3453 0.7530 0.037 Uiso 1 1 calc R U . . .
C4 C 0.03352(13) 0.46224(14) 0.75984(6) 0.0351(3) Uani 1 1 d . . . . .
H4A H -0.0096 0.4089 0.7950 0.042 Uiso 1 1 calc R U . . .
H4B H 0.0930 0.5440 0.7798 0.042 Uiso 1 1 calc R U . . .
C5 C -0.08012(13) 0.52865(13) 0.71267(6) 0.0322(3) Uani 1 1 d . . . . .
C6 C 0.27670(12) 0.34716(13) 0.63180(6) 0.0318(3) Uani 1 1 d . . . . .
C7 C 0.38439(16) 0.3037(2) 0.53555(8) 0.0560(4) Uani 1 1 d . . . . .
H7A H 0.3600 0.2981 0.4885 0.067 Uiso 1 1 calc R U . . .
H7B H 0.4102 0.2034 0.5523 0.067 Uiso 1 1 calc R U . . .
H7C H 0.4636 0.3725 0.5448 0.067 Uiso 1 1 calc R U . . .
C8 C 0.06223(12) 0.19477(13) 0.72237(6) 0.0308(3) Uani 1 1 d . . . . .
C9 C 0.02314(16) -0.02816(14) 0.66214(8) 0.0453(3) Uani 1 1 d . . . . .
H9A H 0.0415 -0.0717 0.6202 0.054 Uiso 1 1 calc R U . . .
H9B H -0.0773 -0.0339 0.6672 0.054 Uiso 1 1 calc R U . . .
H9C H 0.0753 -0.0844 0.6973 0.054 Uiso 1 1 calc R U . . .
C10 C -0.16776(15) 0.64557(15) 0.74290(7) 0.0425(3) Uani 1 1 d . . . . .
H10A H -0.1064 0.7221 0.7646 0.051 Uiso 1 1 calc R U . . .
H10B H -0.2227 0.5974 0.7748 0.051 Uiso 1 1 calc R U . . .
H10C H -0.2311 0.6932 0.7089 0.051 Uiso 1 1 calc R U . . .
C11 C -0.27321(14) 0.44005(17) 0.63996(7) 0.0434(3) Uani 1 1 d . . . . .
H11A H -0.3125 0.3467 0.6207 0.052 Uiso 1 1 calc R U . . .
H11B H -0.2445 0.5058 0.6055 0.052 Uiso 1 1 calc R U . . .
H11C H -0.3442 0.4912 0.6632 0.052 Uiso 1 1 calc R U . . .
C12 C 0.14505(11) 0.64091(12) 0.58506(5) 0.0270(3) Uani 1 1 d . . . . .
C13 C 0.05559(12) 0.68243(13) 0.53101(6) 0.0317(3) Uani 1 1 d . . . . .
H13 H -0.0369 0.6433 0.5255 0.038 Uiso 1 1 calc R U . . .
C14 C 0.10047(13) 0.78017(14) 0.48526(6) 0.0350(3) Uani 1 1 d . . . . .
H14 H 0.0402 0.8059 0.4478 0.042 Uiso 1 1 calc R U . . .
C15 C 0.23536(13) 0.84085(14) 0.49468(6) 0.0333(3) Uani 1 1 d . . . . .
C16 C 0.32457(12) 0.80164(14) 0.54900(6) 0.0338(3) Uani 1 1 d . . . . .
H16 H 0.4158 0.8440 0.5554 0.041 Uiso 1 1 calc R U . . .
C17 C 0.27996(12) 0.70083(13) 0.59357(6) 0.0308(3) Uani 1 1 d . . . . .
H17 H 0.3415 0.6721 0.6302 0.037 Uiso 1 1 calc R U . . .
C18 C 0.28503(14) 0.94471(16) 0.44826(6) 0.0406(3) 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 C1 1.3594(14) . ?
O1 C5 1.4654(13) . ?
O2 C6 1.2034(14) . ?
O3 C6 1.3464(15) . ?
O3 C7 1.4396(16) . ?
O4 C8 1.2015(15) . ?
O5 C8 1.3362(15) . ?
O5 C9 1.4516(15) . ?
O6 C5 1.4028(14) . ?
O6 C11 1.4250(16) . ?
N1 C18 1.1457(17) . ?
C1 C2 1.3455(16) . ?
C1 C12 1.4870(15) . ?
C2 C6 1.4735(16) . ?
C2 C3 1.5080(16) . ?
C3 C8 1.5218(16) . ?
C3 C4 1.5242(17) . ?
C3 H3 1.0000 . ?
C4 C5 1.5124(18) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C10 1.5084(17) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.3929(16) . ?
C12 C17 1.3950(16) . ?
C13 C14 1.3818(17) . ?
C13 H13 0.9500 . ?
C14 C15 1.3983(17) . ?
C14 H14 0.9500 . ?
C15 C16 1.3903(18) . ?
C15 C18 1.4439(17) . ?
C16 C17 1.3812(17) . ?
C16 H16 0.9500 . ?
C17 H17 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
C1 O1 C5 117.17(9) . . ?
C6 O3 C7 115.51(10) . . ?
C8 O5 C9 114.92(10) . . ?
C5 O6 C11 116.55(10) . . ?
C2 C1 O1 124.12(10) . . ?
C2 C1 C12 126.28(10) . . ?
O1 C1 C12 109.28(9) . . ?
C1 C2 C6 122.30(10) . . ?
C1 C2 C3 121.06(10) . . ?
C6 C2 C3 116.21(10) . . ?
C2 C3 C8 115.99(10) . . ?
C2 C3 C4 110.51(10) . . ?
C8 C3 C4 111.86(10) . . ?
C2 C3 H3 105.9 . . ?
C8 C3 H3 105.9 . . ?
C4 C3 H3 105.9 . . ?
C5 C4 C3 110.63(10) . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
O6 C5 O1 108.66(9) . . ?
O6 C5 C10 115.27(10) . . ?
O1 C5 C10 104.37(9) . . ?
O6 C5 C4 105.88(9) . . ?
O1 C5 C4 109.06(9) . . ?
C10 C5 C4 113.46(11) . . ?
O2 C6 O3 122.94(11) . . ?
O2 C6 C2 123.94(12) . . ?
O3 C6 C2 113.10(10) . . ?
O3 C7 H7A 109.5 . . ?
O3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O4 C8 O5 123.45(11) . . ?
O4 C8 C3 123.06(11) . . ?
O5 C8 C3 113.36(10) . . ?
O5 C9 H9A 109.5 . . ?
O5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O6 C11 H11A 109.5 . . ?
O6 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O6 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C17 119.62(11) . . ?
C13 C12 C1 121.35(10) . . ?
C17 C12 C1 118.82(10) . . ?
C14 C13 C12 120.46(11) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 119.39(11) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C16 C15 C14 120.47(11) . . ?
C16 C15 C18 118.68(11) . . ?
C14 C15 C18 120.85(11) . . ?
C17 C16 C15 119.67(11) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C12 120.35(11) . . ?
C16 C17 H17 119.8 . . ?
C12 C17 H17 119.8 . . ?
N1 C18 C15 177.96(15) . . ?

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
C5 O1 C1 C2 -7.70(16) . . . . ?
C5 O1 C1 C12 178.50(9) . . . . ?
O1 C1 C2 C6 178.20(10) . . . . ?
C12 C1 C2 C6 -9.06(18) . . . . ?
O1 C1 C2 C3 -9.67(17) . . . . ?
C12 C1 C2 C3 163.08(10) . . . . ?
C1 C2 C3 C8 118.73(12) . . . . ?
C6 C2 C3 C8 -68.67(13) . . . . ?
C1 C2 C3 C4 -9.93(15) . . . . ?
C6 C2 C3 C4 162.67(10) . . . . ?
C2 C3 C4 C5 44.05(13) . . . . ?
C8 C3 C4 C5 -86.81(12) . . . . ?
C11 O6 C5 O1 -66.11(12) . . . . ?
C11 O6 C5 C10 50.57(14) . . . . ?
C11 O6 C5 C4 176.87(10) . . . . ?
C1 O1 C5 O6 -72.52(12) . . . . ?
C1 O1 C5 C10 164.00(10) . . . . ?
C1 O1 C5 C4 42.45(13) . . . . ?
C3 C4 C5 O6 56.25(12) . . . . ?
C3 C4 C5 O1 -60.50(12) . . . . ?
C3 C4 C5 C10 -176.36(10) . . . . ?
C7 O3 C6 O2 -7.39(18) . . . . ?
C7 O3 C6 C2 174.47(11) . . . . ?
C1 C2 C6 O2 146.47(12) . . . . ?
C3 C2 C6 O2 -26.02(17) . . . . ?
C1 C2 C6 O3 -35.41(15) . . . . ?
C3 C2 C6 O3 152.09(10) . . . . ?
C9 O5 C8 O4 -1.97(17) . . . . ?
C9 O5 C8 C3 173.95(10) . . . . ?
C2 C3 C8 O4 -174.87(11) . . . . ?
C4 C3 C8 O4 -46.87(15) . . . . ?
C2 C3 C8 O5 9.20(14) . . . . ?
C4 C3 C8 O5 137.20(10) . . . . ?
C2 C1 C12 C13 128.80(13) . . . . ?
O1 C1 C12 C13 -57.56(13) . . . . ?
C2 C1 C12 C17 -56.36(16) . . . . ?
O1 C1 C12 C17 117.28(11) . . . . ?
C17 C12 C13 C14 1.21(17) . . . . ?
C1 C12 C13 C14 176.01(11) . . . . ?
C12 C13 C14 C15 -1.93(18) . . . . ?
C13 C14 C15 C16 0.99(19) . . . . ?
C13 C14 C15 C18 -179.25(12) . . . . ?
C14 C15 C16 C17 0.68(18) . . . . ?
C18 C15 C16 C17 -179.08(12) . . . . ?
C15 C16 C17 C12 -1.41(18) . . . . ?
C13 C12 C17 C16 0.48(17) . . . . ?
C1 C12 C17 C16 -174.44(10) . . . . ?

_refine_diff_density_max         0.238
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.037

_shelxl_version_number           2014-3

