# Electronic Supplementary Material (ESI) for ChemComm.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1577519'
_audit_update_record             
;
2017-10-02 deposited with the CCDC.
2018-02-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H29 Br N5 O6'
_chemical_formula_sum            'C23 H29 Br N5 O6'
_chemical_formula_weight         551.42

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'
Br Br -0.2901 2.4595 '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                   10.716(3)
_cell_length_b                   18.530(4)
_cell_length_c                   13.213(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.445(6)
_cell_angle_gamma                90
_cell_volume                     2622.7(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1433
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_F_000             1140
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    1.613
_shelx_estimated_absorpt_T_min   0.739
_shelx_estimated_absorpt_T_max   0.794
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9339
_exptl_absorpt_correction_T_max  0.9552
_exptl_absorpt_process_details   'multi-scan absorption correction'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(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            48439
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.893
_diffrn_reflns_theta_max         28.441
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6594
_reflns_number_gt                4956
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

__computing_data_collection      'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0522P)²+1.2563P] 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         6594
_refine_ls_number_parameters     323
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0349
_refine_ls_wR_factor_ref         0.0964
_refine_ls_wR_factor_gt          0.0865
_refine_ls_goodness_of_fit_ref   0.937
_refine_ls_restrained_S_all      0.937
_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
Br01 Br 0.44257(2) 0.25401(2) 0.57986(2) 0.02904(8) Uani 1 1 d . . . . .
O002 O 0.23838(12) 0.65517(7) 0.33411(10) 0.0223(3) Uani 1 1 d . . . . .
O003 O 0.60678(12) 0.51505(7) 0.65603(11) 0.0260(3) Uani 1 1 d . . . . .
O004 O 0.09985(12) 0.56398(7) 0.35741(11) 0.0252(3) Uani 1 1 d . . . . .
O005 O 0.46496(13) 0.59675(8) 0.60607(12) 0.0290(3) Uani 1 1 d . . . . .
O006 O 0.08394(14) 0.75335(7) 0.47703(13) 0.0302(3) Uani 1 1 d . . . . .
O007 O 0.27190(13) 0.80125(7) 0.52531(12) 0.0298(3) Uani 1 1 d . . . . .
N4 N 0.25198(15) 0.68360(8) 0.52496(12) 0.0214(3) Uani 1 1 d . . . . .
N3 N 0.19418(15) 0.62040(8) 0.49126(12) 0.0204(3) Uani 1 1 d . . . . .
N1 N 0.27252(17) 0.62896(11) 0.83603(14) 0.0325(4) Uani 1 1 d . . . . .
N00B N 0.19727(18) 0.57939(10) 0.84477(14) 0.0315(4) Uani 1 1 d . . . . .
C00C C 0.40184(17) 0.47312(10) 0.63108(14) 0.0185(4) Uani 1 1 d . . . . .
C00D C 0.37295(18) 0.34570(10) 0.60896(15) 0.0215(4) Uani 1 1 d . . . . .
C00E C 0.27221(17) 0.48266(10) 0.63898(14) 0.0186(4) Uani 1 1 d . . . . .
C00F C 0.49095(17) 0.53565(10) 0.63000(14) 0.0198(4) Uani 1 1 d . . . . .
C00G C 0.45136(17) 0.40415(10) 0.61770(15) 0.0204(4) Uani 1 1 d . . . . .
H00G H 0.5373 0.3978 0.6147 0.025 Uiso 1 1 calc R U . . .
C00H C 0.21041(17) 0.55485(10) 0.65578(14) 0.0186(4) Uani 1 1 d . . . . .
H00H H 0.2770 0.5908 0.6644 0.022 Uiso 1 1 calc R U . . .
C00I C 0.24458(18) 0.35312(10) 0.61651(15) 0.0229(4) Uani 1 1 d . . . . .
H00I H 0.1921 0.3133 0.6110 0.027 Uiso 1 1 calc R U . . .
C00J C 0.12435(17) 0.58043(10) 0.56668(15) 0.0205(4) Uani 1 1 d . . . . .
H00J H 0.0852 0.5383 0.5343 0.025 Uiso 1 1 calc R U . . .
C00K C 0.19699(18) 0.42130(10) 0.63237(15) 0.0221(4) Uani 1 1 d . . . . .
H00K H 0.1113 0.4265 0.6389 0.027 Uiso 1 1 calc R U . . .
C00L C 0.1911(2) 0.74801(10) 0.50541(15) 0.0237(4) Uani 1 1 d . . . . .
C00M C 0.02588(17) 0.62358(11) 0.61933(17) 0.0256(4) Uani 1 1 d . . . . .
H00M H -0.0300 0.6544 0.5861 0.031 Uiso 1 1 calc R U . . .
C00N C 0.17027(17) 0.61014(10) 0.38952(15) 0.0200(4) Uani 1 1 d . . . . .
C00O C 0.12805(18) 0.55945(10) 0.74964(15) 0.0231(4) Uani 1 1 d . . . . .
H00O H 0.0887 0.5123 0.7595 0.028 Uiso 1 1 calc R U . . .
C00P C 0.2059(2) 0.66739(11) 0.22566(15) 0.0264(4) Uani 1 1 d . . . . .
C00Q C 0.02831(18) 0.61252(10) 0.71762(17) 0.0260(4) Uani 1 1 d . . . . .
H00Q H -0.0253 0.6349 0.7622 0.031 Uiso 1 1 calc R U . . .
C00R C 0.70152(18) 0.57019(11) 0.64666(17) 0.0271(4) Uani 1 1 d . . . . .
H00A H 0.7123 0.5811 0.5764 0.041 Uiso 1 1 calc R U . . .
H00C H 0.7790 0.5530 0.6757 0.041 Uiso 1 1 calc R U . . .
H00D H 0.6761 0.6129 0.6816 0.041 Uiso 1 1 calc R U . . .
N2 N 0.3447(2) 0.67372(13) 0.83635(19) 0.0525(6) Uani 1 1 d . . . . .
C00T C 0.0740(2) 0.69791(14) 0.21855(18) 0.0362(5) Uani 1 1 d . . . . .
H00E H 0.0156 0.6616 0.2384 0.054 Uiso 1 1 calc R U . . .
H00F H 0.0553 0.7125 0.1501 0.054 Uiso 1 1 calc R U . . .
H00L H 0.0679 0.7389 0.2627 0.054 Uiso 1 1 calc R U . . .
C00U C 0.2330(2) 0.87751(11) 0.51661(16) 0.0292(5) Uani 1 1 d . . . . .
C00V C 0.3008(2) 0.72371(14) 0.19630(18) 0.0362(5) Uani 1 1 d . . . . .
H00N H 0.2929 0.7653 0.2390 0.054 Uiso 1 1 calc R U . . .
H18 H 0.2862 0.7375 0.1269 0.054 Uiso 1 1 calc R U . . .
H00R H 0.3834 0.7041 0.2043 0.054 Uiso 1 1 calc R U . . .
C00W C 0.2226(2) 0.59901(13) 0.16466(18) 0.0392(6) Uani 1 1 d . . . . .
H00S H 0.3043 0.5795 0.1783 0.059 Uiso 1 1 calc R U . . .
H00T H 0.2133 0.6098 0.0938 0.059 Uiso 1 1 calc R U . . .
H00U H 0.1606 0.5643 0.1832 0.059 Uiso 1 1 calc R U . . .
C00X C 0.3540(3) 0.91710(12) 0.5396(2) 0.0475(7) Uani 1 1 d . . . . .
H00V H 0.3834 0.9052 0.6067 0.071 Uiso 1 1 calc R U . . .
H00W H 0.3400 0.9682 0.5349 0.071 Uiso 1 1 calc R U . . .
H15 H 0.4153 0.9031 0.4916 0.071 Uiso 1 1 calc R U . . .
C00Y C 0.1883(3) 0.89293(13) 0.40900(19) 0.0436(6) Uani 1 1 d . . . . .
H14 H 0.2511 0.8782 0.3628 0.065 Uiso 1 1 calc R U . . .
H12 H 0.1728 0.9437 0.4013 0.065 Uiso 1 1 calc R U . . .
H17 H 0.1127 0.8666 0.3947 0.065 Uiso 1 1 calc R U . . .
C00Z C 0.1358(3) 0.89388(14) 0.5939(2) 0.0507(7) Uani 1 1 d . . . . .
H13 H 0.0599 0.8688 0.5762 0.076 Uiso 1 1 calc R U . . .
H11 H 0.1202 0.9449 0.5951 0.076 Uiso 1 1 calc R U . . .
H16 H 0.1654 0.8784 0.6595 0.076 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
Br01 C00D 1.8988(19) . ?
O002 C00N 1.339(2) . ?
O002 C00P 1.483(2) . ?
O003 C00F 1.335(2) . ?
O003 C00R 1.448(2) . ?
O004 C00N 1.210(2) . ?
O005 C00F 1.206(2) . ?
O006 C00L 1.203(3) . ?
O007 C00L 1.334(2) . ?
O007 C00U 1.477(2) . ?
N4 C00L 1.381(2) . ?
N4 N3 1.393(2) . ?
N3 C00N 1.375(3) . ?
N3 C00J 1.463(2) . ?
N1 N2 1.134(3) . ?
N1 N00B 1.230(3) . ?
N00B C00O 1.490(3) . ?
C00C C00G 1.397(3) . ?
C00C C00E 1.407(3) . ?
C00C C00F 1.502(3) . ?
C00D C00G 1.374(3) . ?
C00D C00I 1.389(3) . ?
C00E C00K 1.395(3) . ?
C00E C00H 1.512(2) . ?
C00G H00G 0.9300 . ?
C00H C00O 1.542(3) . ?
C00H C00J 1.551(3) . ?
C00H H00H 0.9800 . ?
C00I C00K 1.380(3) . ?
C00I H00I 0.9300 . ?
C00J C00M 1.508(3) . ?
C00J H00J 0.9800 . ?
C00K H00K 0.9300 . ?
C00M C00Q 1.314(3) . ?
C00M H00M 0.9300 . ?
C00O C00Q 1.505(3) . ?
C00O H00O 0.9800 . ?
C00P C00V 1.514(3) . ?
C00P C00W 1.515(3) . ?
C00P C00T 1.523(3) . ?
C00Q H00Q 0.9300 . ?
C00R H00A 0.9600 . ?
C00R H00C 0.9600 . ?
C00R H00D 0.9600 . ?
C00T H00E 0.9600 . ?
C00T H00F 0.9600 . ?
C00T H00L 0.9600 . ?
C00U C00Z 1.507(3) . ?
C00U C00X 1.514(3) . ?
C00U C00Y 1.516(3) . ?
C00V H00N 0.9600 . ?
C00V H18 0.9600 . ?
C00V H00R 0.9600 . ?
C00W H00S 0.9600 . ?
C00W H00T 0.9600 . ?
C00W H00U 0.9600 . ?
C00X H00V 0.9600 . ?
C00X H00W 0.9600 . ?
C00X H15 0.9600 . ?
C00Y H14 0.9600 . ?
C00Y H12 0.9600 . ?
C00Y H17 0.9600 . ?
C00Z H13 0.9600 . ?
C00Z H11 0.9600 . ?
C00Z H16 0.9600 . ?

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
C00N O002 C00P 120.37(15) . . ?
C00F O003 C00R 115.18(15) . . ?
C00L O007 C00U 120.76(16) . . ?
C00L N4 N3 117.57(15) . . ?
C00N N3 N4 119.94(15) . . ?
C00N N3 C00J 120.67(16) . . ?
N4 N3 C00J 116.04(15) . . ?
N2 N1 N00B 174.2(2) . . ?
N1 N00B C00O 114.82(17) . . ?
C00G C00C C00E 120.23(17) . . ?
C00G C00C C00F 117.46(16) . . ?
C00E C00C C00F 122.21(16) . . ?
C00G C00D C00I 121.39(17) . . ?
C00G C00D Br01 118.68(14) . . ?
C00I C00D Br01 119.88(14) . . ?
C00K C00E C00C 117.57(17) . . ?
C00K C00E C00H 118.42(16) . . ?
C00C C00E C00H 124.00(16) . . ?
O005 C00F O003 122.88(17) . . ?
O005 C00F C00C 125.74(17) . . ?
O003 C00F C00C 111.35(16) . . ?
C00D C00G C00C 119.90(17) . . ?
C00D C00G H00G 120.0 . . ?
C00C C00G H00G 120.0 . . ?
C00E C00H C00O 115.38(15) . . ?
C00E C00H C00J 114.41(15) . . ?
C00O C00H C00J 104.60(15) . . ?
C00E C00H H00H 107.3 . . ?
C00O C00H H00H 107.3 . . ?
C00J C00H H00H 107.3 . . ?
C00K C00I C00D 118.16(18) . . ?
C00K C00I H00I 120.9 . . ?
C00D C00I H00I 120.9 . . ?
N3 C00J C00M 114.94(16) . . ?
N3 C00J C00H 111.55(15) . . ?
C00M C00J C00H 102.79(16) . . ?
N3 C00J H00J 109.1 . . ?
C00M C00J H00J 109.1 . . ?
C00H C00J H00J 109.1 . . ?
C00I C00K C00E 122.71(18) . . ?
C00I C00K H00K 118.6 . . ?
C00E C00K H00K 118.6 . . ?
O006 C00L O007 127.59(18) . . ?
O006 C00L N4 124.87(18) . . ?
O007 C00L N4 107.53(17) . . ?
C00Q C00M C00J 112.12(18) . . ?
C00Q C00M H00M 123.9 . . ?
C00J C00M H00M 123.9 . . ?
O004 C00N O002 126.34(18) . . ?
O004 C00N N3 122.64(18) . . ?
O002 C00N N3 110.96(16) . . ?
N00B C00O C00Q 114.20(17) . . ?
N00B C00O C00H 114.15(16) . . ?
C00Q C00O C00H 103.11(16) . . ?
N00B C00O H00O 108.4 . . ?
C00Q C00O H00O 108.4 . . ?
C00H C00O H00O 108.4 . . ?
O002 C00P C00V 102.13(16) . . ?
O002 C00P C00W 111.01(17) . . ?
C00V C00P C00W 110.58(19) . . ?
O002 C00P C00T 108.11(17) . . ?
C00V C00P C00T 110.87(19) . . ?
C00W C00P C00T 113.53(19) . . ?
C00M C00Q C00O 112.07(18) . . ?
C00M C00Q H00Q 124.0 . . ?
C00O C00Q H00Q 124.0 . . ?
O003 C00R H00A 109.5 . . ?
O003 C00R H00C 109.5 . . ?
H00A C00R H00C 109.5 . . ?
O003 C00R H00D 109.5 . . ?
H00A C00R H00D 109.5 . . ?
H00C C00R H00D 109.5 . . ?
C00P C00T H00E 109.5 . . ?
C00P C00T H00F 109.5 . . ?
H00E C00T H00F 109.5 . . ?
C00P C00T H00L 109.5 . . ?
H00E C00T H00L 109.5 . . ?
H00F C00T H00L 109.5 . . ?
O007 C00U C00Z 109.78(18) . . ?
O007 C00U C00X 102.06(17) . . ?
C00Z C00U C00X 111.7(2) . . ?
O007 C00U C00Y 109.58(17) . . ?
C00Z C00U C00Y 113.0(2) . . ?
C00X C00U C00Y 110.2(2) . . ?
C00P C00V H00N 109.5 . . ?
C00P C00V H18 109.5 . . ?
H00N C00V H18 109.5 . . ?
C00P C00V H00R 109.5 . . ?
H00N C00V H00R 109.5 . . ?
H18 C00V H00R 109.5 . . ?
C00P C00W H00S 109.5 . . ?
C00P C00W H00T 109.5 . . ?
H00S C00W H00T 109.5 . . ?
C00P C00W H00U 109.5 . . ?
H00S C00W H00U 109.5 . . ?
H00T C00W H00U 109.5 . . ?
C00U C00X H00V 109.5 . . ?
C00U C00X H00W 109.5 . . ?
H00V C00X H00W 109.5 . . ?
C00U C00X H15 109.5 . . ?
H00V C00X H15 109.5 . . ?
H00W C00X H15 109.5 . . ?
C00U C00Y H14 109.5 . . ?
C00U C00Y H12 109.5 . . ?
H14 C00Y H12 109.5 . . ?
C00U C00Y H17 109.5 . . ?
H14 C00Y H17 109.5 . . ?
H12 C00Y H17 109.5 . . ?
C00U C00Z H13 109.5 . . ?
C00U C00Z H11 109.5 . . ?
H13 C00Z H11 109.5 . . ?
C00U C00Z H16 109.5 . . ?
H13 C00Z H16 109.5 . . ?
H11 C00Z H16 109.5 . . ?

_refine_diff_density_max         0.756
_refine_diff_density_min         -0.561
_refine_diff_density_rms         0.061

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1577520'
_audit_update_record             
;
2017-10-02 deposited with the CCDC.
2018-02-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H32 N2 O6'
_chemical_formula_sum            'C24 H32 N2 O6'
_chemical_formula_weight         444.51

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'

_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                   13.677(9)
_cell_length_b                   17.670(12)
_cell_length_c                   10.710(7)
_cell_angle_alpha                90
_cell_angle_beta                 106.085(14)
_cell_angle_gamma                90
_cell_volume                     2487(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3286
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_F_000             952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.836
_exptl_absorpt_process_details   
;
R. H. Blessing Acta Crystallogr., Sect. A, 1995, 51, 33-58 
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20346
_diffrn_reflns_av_unetI/netI     0.0871
_diffrn_reflns_av_R_equivalents  0.0778
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.058
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5652
_reflns_number_gt                2455
_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       
;
CrystalClear-SM Expert 2.0 r14k (Rigaku, 2012)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r14k (Rigaku, 2012)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r14k (Rigaku, 2012)
;

_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0643P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5652
_refine_ls_number_parameters     296
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1041
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1219
_refine_ls_wR_factor_gt          0.1050
_refine_ls_goodness_of_fit_ref   0.683
_refine_ls_restrained_S_all      0.683
_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
O16 O 1.29820(11) 0.18136(9) 1.06982(12) 0.0774(5) Uani 1 1 d . . . . .
O17 O 1.27337(9) 0.12866(8) 1.25220(10) 0.0649(4) Uani 1 1 d . . . . .
O23 O 1.12081(10) 0.07669(8) 0.73873(11) 0.0652(4) Uani 1 1 d . . . . .
O24 O 1.22344(9) 0.02632(8) 0.92460(11) 0.0622(4) Uani 1 1 d . . . . .
O30 O 0.92034(10) 0.01394(7) 0.81473(11) 0.0578(3) Uani 1 1 d . . . . .
O31 O 0.83537(11) 0.02930(8) 0.60649(11) 0.0684(4) Uani 1 1 d . . . . .
N13 N 1.11573(11) 0.11803(8) 0.93613(12) 0.0502(4) Uani 1 1 d . . . . .
N14 N 1.15558(10) 0.11442(9) 1.06947(11) 0.0508(4) Uani 1 1 d . . . . .
H14 H 1.1212 0.0926 1.1179 0.061 Uiso 1 1 calc R U . . .
C1 C 0.79839(13) 0.11311(11) 0.75735(16) 0.0503(4) Uani 1 1 d . . . . .
C2 C 0.69992(15) 0.12651(13) 0.68140(19) 0.0688(6) Uani 1 1 d . . . . .
H2 H 0.6709 0.0951 0.6086 0.083 Uiso 1 1 calc R U . . .
C3 C 0.64381(17) 0.18553(15) 0.7113(3) 0.0843(7) Uani 1 1 d . . . . .
H3 H 0.5764 0.1942 0.6587 0.101 Uiso 1 1 calc R U . . .
C4 C 0.68404(17) 0.23130(14) 0.8152(2) 0.0793(7) Uani 1 1 d . . . . .
H4 H 0.6446 0.2715 0.8349 0.095 Uiso 1 1 calc R U . . .
C5 C 0.78244(15) 0.21925(11) 0.89215(19) 0.0615(5) Uani 1 1 d . . . . .
C6 C 0.84030(13) 0.16055(10) 0.86332(16) 0.0481(4) Uani 1 1 d . . . . .
C7 C 0.94513(13) 0.15848(10) 0.95550(15) 0.0472(4) Uani 1 1 d . . . . .
H7 H 0.9561 0.1109 1.0081 0.057 Uiso 1 1 calc R U . . .
C8 C 0.94810(15) 0.22907(11) 1.04361(17) 0.0613(5) Uani 1 1 d . . . . .
H8 H 0.9742 0.2153 1.1376 0.074 Uiso 1 1 calc R U . . .
C9 C 0.83900(17) 0.26017(13) 1.0129(2) 0.0751(6) Uani 1 1 d . . . . .
H9A H 0.8088 0.2496 1.0851 0.090 Uiso 1 1 calc R U . . .
H9B H 0.8380 0.3155 0.9979 0.090 Uiso 1 1 calc R U . . .
C10 C 1.02073(16) 0.28046(12) 1.00362(19) 0.0693(6) Uani 1 1 d . . . . .
H10 H 1.0353 0.3304 1.0364 0.083 Uiso 1 1 calc R U . . .
C11 C 1.06237(15) 0.25026(11) 0.91915(18) 0.0603(5) Uani 1 1 d . . . . .
H11 H 1.1078 0.2765 0.8816 0.072 Uiso 1 1 calc R U . . .
C12 C 1.03063(13) 0.16992(10) 0.88823(15) 0.0470(4) Uani 1 1 d . . . . .
H12 H 1.0023 0.1638 0.7921 0.056 Uiso 1 1 calc R U . . .
C15 C 1.24863(14) 0.14511(12) 1.12479(16) 0.0563(5) Uani 1 1 d . . . . .
C18 C 1.37322(14) 0.14920(14) 1.33821(18) 0.0673(6) Uani 1 1 d . . . . .
C19 C 1.36487(18) 0.12171(17) 1.46931(18) 0.1053(10) Uani 1 1 d . . . . .
H19A H 1.3099 0.1490 1.4922 0.158 Uiso 1 1 calc R U . . .
H19B H 1.4293 0.1310 1.5356 0.158 Uiso 1 1 calc R U . . .
H19C H 1.3501 0.0674 1.4646 0.158 Uiso 1 1 calc R U . . .
C20 C 1.38744(19) 0.23440(15) 1.3398(2) 0.0948(8) Uani 1 1 d . . . . .
H20A H 1.3934 0.2512 1.2550 0.142 Uiso 1 1 calc R U . . .
H20B H 1.4494 0.2480 1.4074 0.142 Uiso 1 1 calc R U . . .
H20C H 1.3287 0.2590 1.3580 0.142 Uiso 1 1 calc R U . . .
C21 C 1.45463(17) 0.10750(16) 1.2958(2) 0.1047(9) Uani 1 1 d . . . . .
H21A H 1.4372 0.0537 1.2851 0.157 Uiso 1 1 calc R U . . .
H21B H 1.5200 0.1135 1.3618 0.157 Uiso 1 1 calc R U . . .
H21C H 1.4597 0.1282 1.2129 0.157 Uiso 1 1 calc R U . . .
C22 C 1.15169(13) 0.07311(11) 0.85582(17) 0.0512(5) Uani 1 1 d . . . . .
C25 C 1.28390(16) -0.01944(13) 0.86083(19) 0.0719(6) Uani 1 1 d . . . . .
C26 C 1.2165(2) -0.07740(15) 0.7745(3) 0.1190(10) Uani 1 1 d . . . . .
H26A H 1.1810 -0.1071 0.8257 0.178 Uiso 1 1 calc R U . . .
H26B H 1.2583 -0.1111 0.7378 0.178 Uiso 1 1 calc R U . . .
H26C H 1.1666 -0.0516 0.7039 0.178 Uiso 1 1 calc R U . . .
C27 C 1.33842(19) 0.03165(17) 0.7886(2) 0.1117(10) Uani 1 1 d . . . . .
H27A H 1.2883 0.0578 0.7185 0.168 Uiso 1 1 calc R U . . .
H27B H 1.3835 0.0012 0.7516 0.168 Uiso 1 1 calc R U . . .
H27C H 1.3788 0.0691 0.8488 0.168 Uiso 1 1 calc R U . . .
C28 C 1.35821(17) -0.05770(15) 0.9748(2) 0.0942(8) Uani 1 1 d . . . . .
H28A H 1.3989 -0.0192 1.0322 0.141 Uiso 1 1 calc R U . . .
H28B H 1.4032 -0.0911 0.9429 0.141 Uiso 1 1 calc R U . . .
H28C H 1.3206 -0.0876 1.0232 0.141 Uiso 1 1 calc R U . . .
C29 C 0.85799(14) 0.04758(11) 0.73196(16) 0.0503(5) Uani 1 1 d . . . . .
C32 C 0.89200(18) -0.03538(13) 0.57826(19) 0.0819(7) Uani 1 1 d . . . . .
H32A H 0.8737 -0.0438 0.4842 0.123 Uiso 1 1 calc R U . . .
H32B H 0.8752 -0.0805 0.6213 0.123 Uiso 1 1 calc R U . . .
H32C H 0.9651 -0.0252 0.6103 0.123 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
O16 C15 1.199(2) . ?
O17 C15 1.344(2) . ?
O17 C18 1.466(2) . ?
O23 C22 1.209(2) . ?
O24 C22 1.337(2) . ?
O24 C25 1.455(2) . ?
O30 C29 1.203(2) . ?
O31 C29 1.332(2) . ?
O31 C32 1.458(2) . ?
N13 C22 1.359(2) . ?
N13 N14 1.3817(18) . ?
N13 C12 1.459(2) . ?
N14 C15 1.359(2) . ?
C1 C2 1.387(3) . ?
C1 C6 1.400(2) . ?
C1 C29 1.484(3) . ?
C2 C3 1.384(3) . ?
C3 C4 1.362(3) . ?
C4 C5 1.386(3) . ?
C5 C6 1.390(3) . ?
C5 C9 1.497(3) . ?
C6 C7 1.499(2) . ?
C7 C12 1.547(2) . ?
C7 C8 1.558(2) . ?
C8 C10 1.494(3) . ?
C8 C9 1.538(3) . ?
C10 C11 1.309(3) . ?
C11 C12 1.495(3) . ?
C18 C21 1.506(3) . ?
C18 C20 1.517(3) . ?
C18 C19 1.520(3) . ?
C25 C26 1.510(3) . ?
C25 C27 1.513(3) . ?
C25 C28 1.514(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 O17 C18 120.88(15) . . ?
C22 O24 C25 120.71(14) . . ?
C29 O31 C32 114.25(15) . . ?
C22 N13 N14 121.27(14) . . ?
C22 N13 C12 122.55(14) . . ?
N14 N13 C12 116.13(13) . . ?
C15 N14 N13 119.06(14) . . ?
C2 C1 C6 119.09(19) . . ?
C2 C1 C29 121.27(18) . . ?
C6 C1 C29 119.57(16) . . ?
C3 C2 C1 120.2(2) . . ?
C4 C3 C2 120.8(2) . . ?
C3 C4 C5 120.0(2) . . ?
C4 C5 C6 120.07(19) . . ?
C4 C5 C9 128.6(2) . . ?
C6 C5 C9 111.26(18) . . ?
C5 C6 C1 119.77(17) . . ?
C5 C6 C7 111.80(16) . . ?
C1 C6 C7 128.43(17) . . ?
C6 C7 C12 113.48(14) . . ?
C6 C7 C8 103.83(14) . . ?
C12 C7 C8 106.33(15) . . ?
C10 C8 C9 113.87(18) . . ?
C10 C8 C7 102.76(16) . . ?
C9 C8 C7 107.20(15) . . ?
C5 C9 C8 104.52(16) . . ?
C11 C10 C8 113.68(18) . . ?
C10 C11 C12 112.65(18) . . ?
N13 C12 C11 111.38(15) . . ?
N13 C12 C7 112.74(14) . . ?
C11 C12 C7 103.39(15) . . ?
O16 C15 O17 126.63(17) . . ?
O16 C15 N14 126.00(17) . . ?
O17 C15 N14 107.36(15) . . ?
O17 C18 C21 109.10(17) . . ?
O17 C18 C20 110.30(18) . . ?
C21 C18 C20 112.7(2) . . ?
O17 C18 C19 101.89(16) . . ?
C21 C18 C19 111.9(2) . . ?
C20 C18 C19 110.4(2) . . ?
O23 C22 O24 126.57(17) . . ?
O23 C22 N13 122.85(17) . . ?
O24 C22 N13 110.58(15) . . ?
O24 C25 C26 109.54(19) . . ?
O24 C25 C27 109.46(19) . . ?
C26 C25 C27 113.3(2) . . ?
O24 C25 C28 102.21(16) . . ?
C26 C25 C28 110.5(2) . . ?
C27 C25 C28 111.3(2) . . ?
O30 C29 O31 122.86(18) . . ?
O30 C29 C1 124.31(16) . . ?
O31 C29 C1 112.83(16) . . ?

_refine_diff_density_max         0.170
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.031

_shelxl_version_number           2013-4

