# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_3f_ic17312
_database_code_depnum_ccdc_archive 'CCDC 1474865'
_audit_update_record             
;
2016-09-23 deposited with the CCDC.
2016-09-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        3f
_chemical_name_common            ic17312
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H26 Br2 N2 O7'
_chemical_formula_weight         626.30

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

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

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

_cell_length_a                   10.4202(7)
_cell_length_b                   12.1455(8)
_cell_length_c                   12.5464(8)
_cell_angle_alpha                61.4060(13)
_cell_angle_beta                 71.1351(14)
_cell_angle_gamma                78.7175(14)
_cell_volume                     1317.70(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3790
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      23.86

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      not_measured
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    3.122
_shelx_estimated_absorpt_T_min   0.509
_shelx_estimated_absorpt_T_max   0.706
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.509
_exptl_absorpt_correction_T_max  0.706
_exptl_absorpt_process_details   'SADABS (Bruker, 2001)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER SMART APEXCCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17236
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.912
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6063
_reflns_number_gt                4832
_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 SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0391P)²+0.8187P] 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         6063
_refine_ls_number_parameters     340
_refine_ls_number_restraints     114
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.0998
_refine_ls_wR_factor_gt          0.0929
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.006
_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 0.34945(4) 0.93549(3) 0.48687(4) 0.05308(12) Uani 1 1 d . . . . .
Br2 Br -0.26477(3) 0.82003(3) -0.09738(3) 0.04837(11) Uani 1 1 d . . . . .
O1 O 0.6020(2) 0.4930(2) 0.06930(19) 0.0396(5) Uani 1 1 d . . . . .
O2 O 0.2445(2) 0.40735(18) 0.44616(17) 0.0374(5) Uani 1 1 d . . . . .
H2 H 0.2195 0.3347 0.4993 0.056 Uiso 1 1 calc R U . . .
O3 O 0.3682(2) 0.8647(2) -0.0433(2) 0.0504(6) Uani 1 1 d . . . . .
O4 O 0.1908(2) 0.85971(19) 0.1070(2) 0.0430(5) Uani 1 1 d . . . . .
O5 O -0.0123(2) 0.4371(2) 0.3911(2) 0.0558(6) Uani 1 1 d . . . . .
O6 O 0.0594(2) 0.3053(2) 0.3129(2) 0.0503(6) Uani 1 1 d . . . . .
N1 N 0.2834(2) 0.8091(2) 0.0556(2) 0.0332(5) Uani 1 1 d . . . . .
N2 N 0.0717(3) 0.3975(2) 0.3233(2) 0.0378(6) Uani 1 1 d . . . . .
C1 C 0.5150(3) 0.4383(3) 0.1644(3) 0.0324(6) Uani 1 1 d . . . . .
C2 C 0.4731(3) 0.3071(3) 0.2119(3) 0.0406(7) Uani 1 1 d . . . . .
H2A H 0.5512 0.2458 0.2272 0.049 Uiso 1 1 calc R U . . .
H2B H 0.4380 0.3022 0.1500 0.049 Uiso 1 1 calc R U . . .
C3 C 0.3626(3) 0.2805(3) 0.3342(3) 0.0377(7) Uani 1 1 d . . . . .
H3A H 0.4006 0.2309 0.4076 0.045 Uiso 1 1 calc R U . . .
H3B H 0.2903 0.2330 0.3417 0.045 Uiso 1 1 calc R U . . .
C4 C 0.3061(3) 0.4095(3) 0.3274(2) 0.0300(6) Uani 1 1 d . . . . .
C5 C 0.4328(3) 0.4912(3) 0.2572(2) 0.0285(6) Uani 1 1 d . . . . .
C6 C 0.4121(2) 0.6344(2) 0.1891(2) 0.0259(5) Uani 1 1 d . . . . .
H6 H 0.4988 0.6643 0.1220 0.031 Uiso 1 1 calc R U . . .
C7 C 0.3026(3) 0.6684(2) 0.1180(2) 0.0262(5) Uani 1 1 d . . . . .
H7 H 0.3388 0.6402 0.0504 0.031 Uiso 1 1 calc R U . . .
C8 C 0.1685(3) 0.6062(2) 0.2009(2) 0.0270(5) Uani 1 1 d . . . . .
H8 H 0.1358 0.6250 0.2751 0.032 Uiso 1 1 calc R U . . .
C9 C 0.2023(3) 0.4655(2) 0.2465(2) 0.0281(6) Uani 1 1 d . . . . .
H9 H 0.2400 0.4491 0.1710 0.034 Uiso 1 1 calc R U . . .
C10 C 0.5243(3) 0.4541(3) 0.3459(3) 0.0371(7) Uani 1 1 d . . . . .
H10A H 0.4735 0.4691 0.4189 0.056 Uiso 1 1 calc R U . . .
H10B H 0.6046 0.5048 0.3006 0.056 Uiso 1 1 calc R U . . .
H10C H 0.5528 0.3650 0.3744 0.056 Uiso 1 1 calc R U . . .
C11 C 0.3904(3) 0.7058(2) 0.2662(2) 0.0263(5) Uani 1 1 d . . . . .
C12 C 0.4657(3) 0.8101(3) 0.2152(3) 0.0331(6) Uani 1 1 d . . . . .
H12 H 0.5271 0.8348 0.1337 0.040 Uiso 1 1 calc R U . . .
C13 C 0.4540(3) 0.8797(3) 0.2794(3) 0.0363(7) Uani 1 1 d . . . . .
H13 H 0.5077 0.9500 0.2436 0.044 Uiso 1 1 calc R U . . .
C14 C 0.3632(3) 0.8444(3) 0.3955(3) 0.0322(6) Uani 1 1 d . . . . .
C15 C 0.2834(3) 0.7434(3) 0.4487(3) 0.0300(6) Uani 1 1 d . . . . .
H15 H 0.2198 0.7213 0.5288 0.036 Uiso 1 1 calc R U . . .
C16 C 0.2974(3) 0.6745(2) 0.3835(2) 0.0288(6) Uani 1 1 d . . . . .
H16 H 0.2426 0.6048 0.4195 0.035 Uiso 1 1 calc R U . . .
C17 C 0.0601(3) 0.6515(3) 0.1296(2) 0.0283(6) Uani 1 1 d . . . . .
C18 C -0.0571(3) 0.7137(3) 0.1690(3) 0.0446(8) Uani 1 1 d . . . . .
H18 H -0.0709 0.7235 0.2427 0.054 Uiso 1 1 calc R U . . .
C19 C -0.1544(3) 0.7616(4) 0.1030(3) 0.0508(9) Uani 1 1 d . . . . .
H19 H -0.2340 0.8053 0.1302 0.061 Uiso 1 1 calc R U . . .
C20 C -0.1351(3) 0.7457(3) -0.0024(3) 0.0355(6) Uani 1 1 d . . . . .
C21 C -0.0218(3) 0.6807(3) -0.0417(3) 0.0340(6) Uani 1 1 d . . . . .
H21 H -0.0106 0.6681 -0.1133 0.041 Uiso 1 1 calc R U . . .
C22 C 0.0756(3) 0.6341(3) 0.0245(3) 0.0323(6) Uani 1 1 d . . . . .
H22 H 0.1543 0.5895 -0.0024 0.039 Uiso 1 1 calc R U . . .
O7 O 0.2013(9) 0.1590(6) 0.6283(6) 0.0738(19) Uani 0.593(9) 1 d . U P A 1
C23 C 0.1206(16) 0.0770(18) 0.6824(17) 0.052(2) Uani 0.593(9) 1 d . U P A 1
C24 C 0.0018(13) 0.0781(13) 0.6382(14) 0.083(3) Uani 0.593(9) 1 d . U P A 1
H24A H -0.0484 0.0021 0.6974 0.124 Uiso 0.593(9) 1 calc R U P A 1
H24B H -0.0584 0.1522 0.6339 0.124 Uiso 0.593(9) 1 calc R U P A 1
H24C H 0.0348 0.0808 0.5544 0.124 Uiso 0.593(9) 1 calc R U P A 1
C25 C 0.117(2) -0.025(2) 0.797(2) 0.078(3) Uani 0.593(9) 1 d . U P A 1
H25A H 0.0419 -0.0771 0.8198 0.117 Uiso 0.593(9) 1 calc R U P A 1
H25B H 0.2027 -0.0750 0.7921 0.117 Uiso 0.593(9) 1 calc R U P A 1
H25C H 0.1025 0.0032 0.8613 0.117 Uiso 0.593(9) 1 calc R U P A 1
O7' O 0.1288(13) 0.1822(9) 0.6027(10) 0.0738(19) Uani 0.407(9) 1 d . U P A 2
C23' C 0.086(3) 0.081(3) 0.666(3) 0.052(2) Uani 0.407(9) 1 d . U P A 2
C24' C 0.003(2) 0.028(2) 0.625(2) 0.083(3) Uani 0.407(9) 1 d . U P A 2
H24D H -0.0228 -0.0566 0.6907 0.124 Uiso 0.407(9) 1 calc R U P A 2
H24E H -0.0792 0.0820 0.6109 0.124 Uiso 0.407(9) 1 calc R U P A 2
H24F H 0.0565 0.0239 0.5468 0.124 Uiso 0.407(9) 1 calc R U P A 2
C25' C 0.147(4) -0.011(4) 0.793(4) 0.078(3) Uani 0.407(9) 1 d . U P A 2
H25D H 0.1060 -0.0924 0.8398 0.117 Uiso 0.407(9) 1 calc R U P A 2
H25E H 0.2462 -0.0231 0.7653 0.117 Uiso 0.407(9) 1 calc R U P A 2
H25F H 0.1258 0.0302 0.8484 0.117 Uiso 0.407(9) 1 calc R U P A 2


_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 C14 1.899(3) . ?
Br2 C20 1.895(3) . ?
O1 C1 1.210(3) . ?
O2 C4 1.409(3) . ?
O3 N1 1.224(3) . ?
O4 N1 1.213(3) . ?
O5 N2 1.210(3) . ?
O6 N2 1.224(3) . ?
N1 C7 1.503(3) . ?
N2 C9 1.514(3) . ?
C1 C2 1.510(4) . ?
C1 C5 1.535(4) . ?
C2 C3 1.521(4) . ?
C3 C4 1.534(4) . ?
C4 C9 1.556(4) . ?
C4 C5 1.558(4) . ?
C5 C6 1.534(4) . ?
C5 C10 1.545(4) . ?
C6 C11 1.524(4) . ?
C6 C7 1.546(3) . ?
C7 C8 1.524(3) . ?
C8 C17 1.523(4) . ?
C8 C9 1.527(4) . ?
C11 C12 1.386(4) . ?
C11 C16 1.391(4) . ?
C12 C13 1.387(4) . ?
C13 C14 1.368(4) . ?
C14 C15 1.377(4) . ?
C15 C16 1.386(4) . ?
C17 C18 1.382(4) . ?
C17 C22 1.388(4) . ?
C18 C19 1.380(4) . ?
C19 C20 1.374(4) . ?
C20 C21 1.375(4) . ?
C21 C22 1.382(4) . ?
O7 C23 1.212(17) . ?
C23 C25 1.37(3) . ?
C23 C24 1.508(14) . ?
O7' C23' 1.18(3) . ?
C23' C24' 1.50(3) . ?
C23' C25' 1.70(4) . ?

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 N1 O3 124.6(3) . . ?
O4 N1 C7 119.3(2) . . ?
O3 N1 C7 116.0(2) . . ?
O5 N2 O6 124.6(2) . . ?
O5 N2 C9 118.2(2) . . ?
O6 N2 C9 117.1(2) . . ?
O1 C1 C2 125.6(3) . . ?
O1 C1 C5 124.9(3) . . ?
C2 C1 C5 109.6(2) . . ?
C1 C2 C3 105.7(2) . . ?
C2 C3 C4 105.6(2) . . ?
O2 C4 C3 113.7(2) . . ?
O2 C4 C9 109.5(2) . . ?
C3 C4 C9 109.9(2) . . ?
O2 C4 C5 110.8(2) . . ?
C3 C4 C5 103.9(2) . . ?
C9 C4 C5 108.9(2) . . ?
C6 C5 C1 111.2(2) . . ?
C6 C5 C10 110.4(2) . . ?
C1 C5 C10 102.8(2) . . ?
C6 C5 C4 119.0(2) . . ?
C1 C5 C4 102.0(2) . . ?
C10 C5 C4 110.0(2) . . ?
C11 C6 C5 117.0(2) . . ?
C11 C6 C7 113.2(2) . . ?
C5 C6 C7 109.3(2) . . ?
N1 C7 C8 111.6(2) . . ?
N1 C7 C6 107.4(2) . . ?
C8 C7 C6 114.0(2) . . ?
C17 C8 C7 112.0(2) . . ?
C17 C8 C9 111.8(2) . . ?
C7 C8 C9 105.2(2) . . ?
N2 C9 C8 108.2(2) . . ?
N2 C9 C4 108.5(2) . . ?
C8 C9 C4 115.2(2) . . ?
C12 C11 C16 117.8(2) . . ?
C12 C11 C6 118.0(2) . . ?
C16 C11 C6 124.2(2) . . ?
C11 C12 C13 122.0(3) . . ?
C14 C13 C12 118.4(3) . . ?
C13 C14 C15 121.8(3) . . ?
C13 C14 Br1 119.0(2) . . ?
C15 C14 Br1 119.3(2) . . ?
C14 C15 C16 119.0(3) . . ?
C15 C16 C11 121.1(2) . . ?
C18 C17 C22 118.5(3) . . ?
C18 C17 C8 119.4(2) . . ?
C22 C17 C8 122.1(2) . . ?
C19 C18 C17 121.0(3) . . ?
C20 C19 C18 119.3(3) . . ?
C19 C20 C21 121.1(3) . . ?
C19 C20 Br2 118.8(2) . . ?
C21 C20 Br2 120.1(2) . . ?
C20 C21 C22 119.1(3) . . ?
C21 C22 C17 121.0(3) . . ?
O7 C23 C25 125.7(11) . . ?
O7 C23 C24 124.6(13) . . ?
C25 C23 C24 109.5(14) . . ?
O7' C23' C24' 122.3(19) . . ?
O7' C23' C25' 115.4(18) . . ?
C24' C23' C25' 121(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O7' 0.84 1.90 2.721(10) 166.8 .
O2 H2 O7 0.84 1.97 2.791(6) 167.4 .

_refine_diff_density_max         0.760
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_3a_ic17001
_database_code_depnum_ccdc_archive 'CCDC 1474917'
_audit_update_record             
;
2016-09-23 deposited with the CCDC.
2016-09-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        3a
_chemical_name_common            ic17001
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H22 N2 O6'
_chemical_formula_weight         410.42

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.4563(7)
_cell_length_b                   6.7710(4)
_cell_length_c                   25.4114(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.8075(14)
_cell_angle_gamma                90.00
_cell_volume                     1966.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    3556
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      24.34

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      not_measured
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9604
_exptl_absorpt_correction_T_max  0.9949
_exptl_absorpt_process_details   'SADABS (Bruker, 2001)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER SMART APEXCCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14689
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.61
_diffrn_reflns_theta_max         27.50
_reflns_number_total             4514
_reflns_number_gt                3593
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0627P)²+0.6994P] 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         4514
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0586
_refine_ls_wR_factor_ref         0.1460
_refine_ls_wR_factor_gt          0.1365
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.109
_refine_ls_shift/su_max          0.002
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.54065(13) -0.0499(2) 0.12294(6) 0.0376(4) Uani 1 1 d . . .
O2 O 0.42600(12) 0.61284(18) 0.08705(5) 0.0255(3) Uani 1 1 d . . .
H2 H 0.4578 0.7186 0.0977 0.038 Uiso 1 1 calc R . .
O3 O 0.13121(14) -0.0623(2) 0.11933(6) 0.0416(4) Uani 1 1 d . . .
O4 O 0.06561(13) 0.2366(2) 0.11876(6) 0.0399(4) Uani 1 1 d . . .
O5 O 0.48775(15) 0.6198(2) 0.23931(6) 0.0432(4) Uani 1 1 d . . .
O6 O 0.35752(14) 0.7671(2) 0.18804(7) 0.0386(4) Uani 1 1 d . . .
N1 N 0.14411(15) 0.1158(3) 0.12407(6) 0.0287(4) Uani 1 1 d . . .
N2 N 0.41631(14) 0.6239(2) 0.20144(6) 0.0255(4) Uani 1 1 d . . .
C1 C 0.54335(17) 0.1270(3) 0.12081(8) 0.0249(4) Uani 1 1 d . . .
C2 C 0.63837(18) 0.2558(3) 0.14644(9) 0.0295(5) Uani 1 1 d . . .
H2A H 0.7146 0.2265 0.1319 0.035 Uiso 1 1 calc R . .
H2B H 0.6456 0.2341 0.1850 0.035 Uiso 1 1 calc R . .
C3 C 0.60081(17) 0.4683(3) 0.13375(8) 0.0256(4) Uani 1 1 d . . .
H3A H 0.6429 0.5208 0.1040 0.031 Uiso 1 1 calc R . .
H3B H 0.6168 0.5548 0.1648 0.031 Uiso 1 1 calc R . .
C4 C 0.46866(16) 0.4558(3) 0.11892(7) 0.0198(4) Uani 1 1 d . . .
C5 C 0.45410(17) 0.2570(3) 0.08902(7) 0.0210(4) Uani 1 1 d . . .
C6 C 0.33056(16) 0.1649(3) 0.08307(7) 0.0219(4) Uani 1 1 d . . .
H6 H 0.3436 0.0198 0.0791 0.026 Uiso 1 1 calc R . .
C7 C 0.26837(16) 0.1873(3) 0.13485(7) 0.0220(4) Uani 1 1 d . . .
H7 H 0.3076 0.0954 0.1613 0.026 Uiso 1 1 calc R . .
C8 C 0.27051(16) 0.3919(3) 0.15928(7) 0.0207(4) Uani 1 1 d . . .
H8 H 0.2344 0.4890 0.1334 0.025 Uiso 1 1 calc R . .
C9 C 0.40131(16) 0.4372(2) 0.16954(7) 0.0191(4) Uani 1 1 d . . .
H9 H 0.4373 0.3267 0.1911 0.023 Uiso 1 1 calc R . .
C10 C 0.25320(17) 0.2254(3) 0.03452(7) 0.0260(4) Uani 1 1 d . . .
C11 C 0.2068(2) 0.0750(3) 0.00241(9) 0.0382(5) Uani 1 1 d . . .
H11 H 0.2277 -0.0581 0.0101 0.046 Uiso 1 1 calc R . .
C12 C 0.1304(2) 0.1163(4) -0.04070(10) 0.0513(7) Uani 1 1 d . . .
H12 H 0.0985 0.0115 -0.0619 0.062 Uiso 1 1 calc R . .
C13 C 0.1007(2) 0.3071(4) -0.05288(9) 0.0481(7) Uani 1 1 d . . .
H13 H 0.0490 0.3352 -0.0827 0.058 Uiso 1 1 calc R . .
C14 C 0.1462(2) 0.4585(4) -0.02164(9) 0.0421(6) Uani 1 1 d . . .
H14 H 0.1257 0.5913 -0.0300 0.051 Uiso 1 1 calc R . .
C15 C 0.22164(19) 0.4183(3) 0.02188(8) 0.0329(5) Uani 1 1 d . . .
H15 H 0.2521 0.5238 0.0433 0.039 Uiso 1 1 calc R . .
C16 C 0.20872(16) 0.4019(3) 0.21055(7) 0.0240(4) Uani 1 1 d . . .
C17 C 0.13456(18) 0.5583(3) 0.21912(8) 0.0316(5) Uani 1 1 d . . .
H17 H 0.1187 0.6532 0.1921 0.038 Uiso 1 1 calc R . .
C18 C 0.0832(2) 0.5782(4) 0.26664(9) 0.0382(5) Uani 1 1 d . . .
H18 H 0.0333 0.6872 0.2723 0.046 Uiso 1 1 calc R . .
C19 C 0.10467(18) 0.4392(4) 0.30566(8) 0.0386(6) Uani 1 1 d . . .
H19 H 0.0696 0.4523 0.3383 0.046 Uiso 1 1 calc R . .
C20 C 0.1766(2) 0.2821(4) 0.29738(9) 0.0409(6) Uani 1 1 d . . .
H20 H 0.1903 0.1856 0.3242 0.049 Uiso 1 1 calc R . .
C21 C 0.22964(18) 0.2628(3) 0.25016(8) 0.0322(5) Uani 1 1 d . . .
H21 H 0.2803 0.1545 0.2449 0.039 Uiso 1 1 calc R . .
C22 C 0.5048(2) 0.2700(3) 0.03452(8) 0.0308(5) Uani 1 1 d . . .
H22A H 0.5866 0.3132 0.0388 0.046 Uiso 1 1 calc R . .
H22B H 0.4594 0.3651 0.0125 0.046 Uiso 1 1 calc R . .
H22C H 0.5008 0.1398 0.0176 0.046 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.200(2) . ?
O2 C4 1.405(2) . ?
O3 N1 1.220(2) . ?
O4 N1 1.216(2) . ?
O5 N2 1.221(2) . ?
O6 N2 1.217(2) . ?
N1 C7 1.511(2) . ?
N2 C9 1.505(2) . ?
C1 C2 1.508(3) . ?
C1 C5 1.537(3) . ?
C2 C3 1.530(3) . ?
C3 C4 1.538(3) . ?
C4 C9 1.548(2) . ?
C4 C5 1.549(2) . ?
C5 C22 1.539(3) . ?
C5 C6 1.545(3) . ?
C6 C10 1.527(3) . ?
C6 C7 1.545(3) . ?
C7 C8 1.518(3) . ?
C8 C16 1.525(3) . ?
C8 C9 1.535(3) . ?
C10 C15 1.387(3) . ?
C10 C11 1.388(3) . ?
C11 C12 1.384(3) . ?
C12 C13 1.366(4) . ?
C13 C14 1.377(4) . ?
C14 C15 1.385(3) . ?
C16 C17 1.384(3) . ?
C16 C21 1.388(3) . ?
C17 C18 1.385(3) . ?
C18 C19 1.377(3) . ?
C19 C20 1.371(3) . ?
C20 C21 1.387(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
O4 N1 O3 124.74(18) . . ?
O4 N1 C7 119.05(16) . . ?
O3 N1 C7 116.15(17) . . ?
O6 N2 O5 124.62(17) . . ?
O6 N2 C9 118.52(16) . . ?
O5 N2 C9 116.87(16) . . ?
O1 C1 C2 125.30(19) . . ?
O1 C1 C5 125.26(18) . . ?
C2 C1 C5 109.37(15) . . ?
C1 C2 C3 105.53(16) . . ?
C2 C3 C4 104.98(15) . . ?
O2 C4 C3 113.50(14) . . ?
O2 C4 C9 111.53(14) . . ?
C3 C4 C9 109.73(15) . . ?
O2 C4 C5 110.66(14) . . ?
C3 C4 C5 103.89(14) . . ?
C9 C4 C5 107.09(14) . . ?
C1 C5 C22 103.16(15) . . ?
C1 C5 C6 113.15(15) . . ?
C22 C5 C6 109.46(15) . . ?
C1 C5 C4 101.16(14) . . ?
C22 C5 C4 110.92(14) . . ?
C6 C5 C4 117.83(15) . . ?
C10 C6 C7 112.72(15) . . ?
C10 C6 C5 116.70(15) . . ?
C7 C6 C5 110.39(14) . . ?
N1 C7 C8 110.84(15) . . ?
N1 C7 C6 107.24(14) . . ?
C8 C7 C6 116.25(15) . . ?
C7 C8 C16 113.23(15) . . ?
C7 C8 C9 103.96(14) . . ?
C16 C8 C9 110.44(15) . . ?
N2 C9 C8 109.56(14) . . ?
N2 C9 C4 109.51(14) . . ?
C8 C9 C4 114.19(15) . . ?
C15 C10 C11 118.09(19) . . ?
C15 C10 C6 124.62(17) . . ?
C11 C10 C6 117.20(18) . . ?
C12 C11 C10 120.9(2) . . ?
C13 C12 C11 120.4(2) . . ?
C12 C13 C14 119.6(2) . . ?
C13 C14 C15 120.4(2) . . ?
C14 C15 C10 120.6(2) . . ?
C17 C16 C21 118.90(18) . . ?
C17 C16 C8 119.56(17) . . ?
C21 C16 C8 121.46(17) . . ?
C16 C17 C18 120.9(2) . . ?
C19 C18 C17 119.7(2) . . ?
C20 C19 C18 120.0(2) . . ?
C19 C20 C21 120.5(2) . . ?
C20 C21 C16 120.0(2) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.051
####################################################################### 
# 
# 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_3i_first_crystal_ic17971
_database_code_depnum_ccdc_archive 'CCDC 1485986'
_audit_update_record             
;
2016-09-23 deposited with the CCDC.
2016-09-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        3i
_chemical_name_common            'first crystal ic17971'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H20 N4 O10'
_chemical_formula_weight         500.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   9.3887(2)
_cell_length_b                   11.6113(3)
_cell_length_c                   19.7433(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2152.32(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9940
_cell_measurement_theta_min      4.42
_cell_measurement_theta_max      70.05

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.222
_exptl_crystal_size_mid          0.182
_exptl_crystal_size_min          0.166
_exptl_absorpt_coefficient_mu    1.064
_shelx_estimated_absorpt_T_min   0.798
_shelx_estimated_absorpt_T_max   0.843
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6531
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10046
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.417
_diffrn_reflns_theta_max         69.904
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             4021
_reflns_number_gt                3969
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_max     0.980
_reflns_Friedel_fraction_full    0.981

_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0446P)²+0.3428P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0039(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1682 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.06(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4021
_refine_ls_number_parameters     328
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0255
_refine_ls_wR_factor_ref         0.0701
_refine_ls_wR_factor_gt          0.0698
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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 0.68729(15) 0.65448(12) 0.91768(7) 0.0336(3) Uani 1 1 d . . . . .
O2 O 0.45526(13) 0.30639(10) 0.98683(7) 0.0255(3) Uani 1 1 d . . . . .
H2 H 0.4962 0.2548 0.9643 0.038 Uiso 1 1 calc R U . . .
O3 O 0.22974(17) 0.76877(11) 0.93703(7) 0.0343(3) Uani 1 1 d . . . . .
O4 O 0.10838(14) 0.64100(12) 0.99190(8) 0.0311(3) Uani 1 1 d . . . . .
O5 O 0.38832(16) 0.34847(12) 1.12809(8) 0.0332(3) Uani 1 1 d . . . . .
O6 O 0.60266(17) 0.40665(15) 1.14790(8) 0.0403(4) Uani 1 1 d . . . . .
O7 O 0.41918(18) 0.65517(16) 0.76928(8) 0.0457(4) Uani 1 1 d . . . . .
O8 O 0.2277(2) 0.75795(14) 0.77685(10) 0.0547(5) Uani 1 1 d . . . . .
O9 O 0.09513(17) 0.39583(13) 1.07535(9) 0.0439(4) Uani 1 1 d . . . . .
O10 O -0.07032(18) 0.4849(2) 1.12700(11) 0.0647(6) Uani 1 1 d . . . . .
N1 N 0.21995(17) 0.68133(12) 0.97116(7) 0.0235(3) Uani 1 1 d . . . . .
N2 N 0.49391(17) 0.40495(13) 1.11404(8) 0.0259(3) Uani 1 1 d . . . . .
N3 N 0.2961(2) 0.66993(14) 0.78724(8) 0.0316(4) Uani 1 1 d . . . . .
N4 N 0.05403(17) 0.47416(15) 1.11100(8) 0.0291(4) Uani 1 1 d . . . . .
C1 C 0.67306(19) 0.55672(16) 0.93681(9) 0.0233(4) Uani 1 1 d . . . . .
C2 C 0.78040(18) 0.48735(17) 0.97651(10) 0.0278(4) Uani 1 1 d . . . . .
H2A H 0.8120 0.5303 1.0172 0.033 Uiso 1 1 calc R U . . .
H2B H 0.8647 0.4696 0.9483 0.033 Uiso 1 1 calc R U . . .
C3 C 0.70307(19) 0.37650(15) 0.99685(10) 0.0250(4) Uani 1 1 d . . . . .
H3A H 0.7263 0.3550 1.0441 0.030 Uiso 1 1 calc R U . . .
H3B H 0.7299 0.3122 0.9665 0.030 Uiso 1 1 calc R U . . .
C4 C 0.54305(18) 0.40508(13) 0.98970(9) 0.0194(3) Uani 1 1 d . . . . .
C5 C 0.53722(18) 0.48440(14) 0.92575(9) 0.0198(3) Uani 1 1 d . . . . .
C6 C 0.40718(18) 0.56520(14) 0.91539(8) 0.0193(3) Uani 1 1 d . . . . .
H6 H 0.4429 0.6315 0.8879 0.023 Uiso 1 1 calc R U . . .
C7 C 0.35831(17) 0.61749(14) 0.98438(9) 0.0183(3) Uani 1 1 d . . . . .
H7 H 0.4313 0.6751 0.9989 0.022 Uiso 1 1 calc R U . . .
C8 C 0.34188(17) 0.52884(14) 1.04128(9) 0.0179(3) Uani 1 1 d . . . . .
H8 H 0.2747 0.4669 1.0266 0.022 Uiso 1 1 calc R U . . .
C9 C 0.49170(18) 0.47768(14) 1.05057(9) 0.0195(3) Uani 1 1 d . . . . .
H9 H 0.5601 0.5428 1.0569 0.023 Uiso 1 1 calc R U . . .
C10 C 0.5650(2) 0.41390(17) 0.86080(9) 0.0277(4) Uani 1 1 d . . . . .
H10A H 0.5605 0.4649 0.8213 0.042 Uiso 1 1 calc R U . . .
H10B H 0.4925 0.3536 0.8565 0.042 Uiso 1 1 calc R U . . .
H10C H 0.6596 0.3785 0.8633 0.042 Uiso 1 1 calc R U . . .
C11 C 0.28115(18) 0.51633(14) 0.87632(9) 0.0202(3) Uani 1 1 d . . . . .
C12 C 0.22249(19) 0.57329(15) 0.82030(9) 0.0233(4) Uani 1 1 d . . . . .
C13 C 0.0950(2) 0.54164(17) 0.79012(10) 0.0288(4) Uani 1 1 d . . . . .
H13 H 0.0588 0.5838 0.7527 0.035 Uiso 1 1 calc R U . . .
C14 C 0.0215(2) 0.44800(17) 0.81524(11) 0.0326(4) Uani 1 1 d . . . . .
H14 H -0.0667 0.4257 0.7956 0.039 Uiso 1 1 calc R U . . .
C15 C 0.0770(2) 0.38707(17) 0.86919(11) 0.0301(4) Uani 1 1 d . . . . .
H15 H 0.0277 0.3217 0.8861 0.036 Uiso 1 1 calc R U . . .
C16 C 0.2044(2) 0.42060(14) 0.89888(9) 0.0242(4) Uani 1 1 d . . . . .
H16 H 0.2407 0.3770 0.9358 0.029 Uiso 1 1 calc R U . . .
C17 C 0.28870(18) 0.58231(13) 1.10709(9) 0.0191(3) Uani 1 1 d . . . . .
C18 C 0.15600(18) 0.56069(15) 1.13716(9) 0.0220(3) Uani 1 1 d . . . . .
C19 C 0.1106(2) 0.61879(17) 1.19469(10) 0.0279(4) Uani 1 1 d . . . . .
H19 H 0.0184 0.6046 1.2127 0.033 Uiso 1 1 calc R U . . .
C20 C 0.1998(2) 0.69728(16) 1.22571(9) 0.0297(4) Uani 1 1 d . . . . .
H20 H 0.1697 0.7369 1.2653 0.036 Uiso 1 1 calc R U . . .
C21 C 0.3327(2) 0.71773(15) 1.19884(10) 0.0279(4) Uani 1 1 d . . . . .
H21 H 0.3953 0.7702 1.2207 0.033 Uiso 1 1 calc R U . . .
C22 C 0.37562(19) 0.66218(14) 1.14001(9) 0.0227(3) Uani 1 1 d . . . . .
H22 H 0.4668 0.6790 1.1216 0.027 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
O1 C1 1.204(2) . ?
O2 C4 1.413(2) . ?
O3 N1 1.222(2) . ?
O4 N1 1.218(2) . ?
O5 N2 1.221(2) . ?
O6 N2 1.221(2) . ?
O7 N3 1.221(3) . ?
O8 N3 1.224(2) . ?
O9 N4 1.213(2) . ?
O10 N4 1.216(2) . ?
N1 C7 1.518(2) . ?
N2 C9 1.511(2) . ?
N3 C12 1.471(2) . ?
N4 C18 1.481(2) . ?
C1 C2 1.510(3) . ?
C1 C5 1.542(2) . ?
C2 C3 1.531(3) . ?
C3 C4 1.545(2) . ?
C4 C9 1.545(2) . ?
C4 C5 1.564(2) . ?
C5 C10 1.543(2) . ?
C5 C6 1.553(2) . ?
C6 C11 1.522(2) . ?
C6 C7 1.560(2) . ?
C7 C8 1.531(2) . ?
C8 C17 1.524(2) . ?
C8 C9 1.538(2) . ?
C11 C16 1.397(3) . ?
C11 C12 1.401(2) . ?
C12 C13 1.386(3) . ?
C13 C14 1.380(3) . ?
C14 C15 1.381(3) . ?
C15 C16 1.388(3) . ?
C17 C22 1.396(2) . ?
C17 C18 1.403(2) . ?
C18 C19 1.388(3) . ?
C19 C20 1.381(3) . ?
C20 C21 1.376(3) . ?
C21 C22 1.389(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
O4 N1 O3 124.70(15) . . ?
O4 N1 C7 119.35(13) . . ?
O3 N1 C7 115.86(15) . . ?
O6 N2 O5 124.31(16) . . ?
O6 N2 C9 117.16(16) . . ?
O5 N2 C9 118.53(15) . . ?
O7 N3 O8 124.4(2) . . ?
O7 N3 C12 117.82(17) . . ?
O8 N3 C12 117.68(18) . . ?
O10 N4 O9 122.21(19) . . ?
O10 N4 C18 117.43(18) . . ?
O9 N4 C18 120.36(15) . . ?
O1 C1 C2 126.29(17) . . ?
O1 C1 C5 124.11(17) . . ?
C2 C1 C5 109.57(15) . . ?
C1 C2 C3 105.55(14) . . ?
C2 C3 C4 104.87(13) . . ?
O2 C4 C3 113.38(13) . . ?
O2 C4 C9 106.96(13) . . ?
C3 C4 C9 110.46(14) . . ?
O2 C4 C5 115.14(14) . . ?
C3 C4 C5 103.55(13) . . ?
C9 C4 C5 107.20(12) . . ?
C10 C5 C1 105.46(13) . . ?
C10 C5 C6 110.10(14) . . ?
C1 C5 C6 109.86(13) . . ?
C10 C5 C4 110.64(13) . . ?
C1 C5 C4 100.22(13) . . ?
C6 C5 C4 119.31(13) . . ?
C11 C6 C5 116.91(14) . . ?
C11 C6 C7 111.03(13) . . ?
C5 C6 C7 110.56(13) . . ?
N1 C7 C8 111.60(13) . . ?
N1 C7 C6 106.95(13) . . ?
C8 C7 C6 114.11(13) . . ?
C17 C8 C7 112.62(13) . . ?
C17 C8 C9 110.81(14) . . ?
C7 C8 C9 104.78(13) . . ?
N2 C9 C8 109.11(13) . . ?
N2 C9 C4 109.62(12) . . ?
C8 C9 C4 113.79(14) . . ?
C16 C11 C12 115.11(16) . . ?
C16 C11 C6 122.39(16) . . ?
C12 C11 C6 121.97(15) . . ?
C13 C12 C11 123.59(17) . . ?
C13 C12 N3 114.66(16) . . ?
C11 C12 N3 121.71(16) . . ?
C14 C13 C12 119.10(19) . . ?
C15 C14 C13 119.43(18) . . ?
C14 C15 C16 120.52(18) . . ?
C15 C16 C11 122.19(18) . . ?
C22 C17 C18 116.17(16) . . ?
C22 C17 C8 118.42(15) . . ?
C18 C17 C8 125.37(15) . . ?
C19 C18 C17 122.15(17) . . ?
C19 C18 N4 114.61(16) . . ?
C17 C18 N4 123.23(16) . . ?
C20 C19 C18 119.81(18) . . ?
C21 C20 C19 119.53(17) . . ?
C20 C21 C22 120.37(18) . . ?
C21 C22 C17 121.89(17) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O9 0.84 2.13 2.9572(19) 168.7 4_557
C2 H2A O3 0.99 2.62 3.340(2) 129.8 4_567
C2 H2A O10 0.99 2.49 3.285(3) 137.1 1_655
C3 H3A O6 0.99 2.43 3.147(2) 128.8 .
C6 H6 O7 1.00 2.37 3.070(2) 126.5 .
C6 H6 N3 1.00 2.46 2.995(2) 113.0 .
C8 H8 O9 1.00 2.11 2.864(2) 130.8 .
C13 H13 O5 0.95 2.63 3.448(2) 144.6 2_564
C13 H13 O6 0.95 2.57 3.419(2) 149.4 2_564

_refine_diff_density_max         0.227
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_3i_second_crystal_ic18028
_database_code_depnum_ccdc_archive 'CCDC 1488798'
_audit_update_record             
;
2016-09-23 deposited with the CCDC.
2016-09-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        3i
_chemical_name_common            'second crystal ic18028'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H20 N4 O10'
_chemical_formula_weight         500.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   9.3839(2)
_cell_length_b                   11.6090(2)
_cell_length_c                   19.7514(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2151.67(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9814
_cell_measurement_theta_min      3.81
_cell_measurement_theta_max      70.11

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.333
_exptl_crystal_size_mid          0.298
_exptl_crystal_size_min          0.157
_exptl_absorpt_coefficient_mu    1.064
_shelx_estimated_absorpt_T_min   0.718
_shelx_estimated_absorpt_T_max   0.851
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6145
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12358
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.418
_diffrn_reflns_theta_max         69.962
_diffrn_reflns_theta_full        67.679
_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 0.999
_reflns_number_total             4066
_reflns_number_gt                4015
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.747
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.999

_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0321P)²+0.4379P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0047(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1705 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.01(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4066
_refine_ls_number_parameters     328
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0245
_refine_ls_R_factor_gt           0.0240
_refine_ls_wR_factor_ref         0.0621
_refine_ls_wR_factor_gt          0.0617
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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 1.18730(15) 0.84551(12) 0.08226(7) 0.0347(3) Uani 1 1 d . . . . .
O2 O 0.95526(13) 1.19361(10) 0.01313(7) 0.0263(3) Uani 1 1 d . . . . .
H2 H 0.9966 1.2455 0.0353 0.039 Uiso 1 1 calc R U . . .
O3 O 0.72972(17) 0.73110(11) 0.06303(7) 0.0354(3) Uani 1 1 d . . . . .
O4 O 0.60840(14) 0.85899(12) 0.00801(7) 0.0320(3) Uani 1 1 d . . . . .
O5 O 0.88844(15) 1.15158(11) -0.12811(7) 0.0342(3) Uani 1 1 d . . . . .
O6 O 1.10273(16) 1.09336(14) -0.14797(7) 0.0414(4) Uani 1 1 d . . . . .
O7 O 0.91931(18) 0.84491(15) 0.23075(8) 0.0469(4) Uani 1 1 d . . . . .
O8 O 0.7276(2) 0.74215(14) 0.22317(9) 0.0554(5) Uani 1 1 d . . . . .
O9 O 0.59525(16) 1.10423(13) -0.07538(9) 0.0446(4) Uani 1 1 d . . . . .
O10 O 0.42979(17) 1.0148(2) -0.12695(10) 0.0659(6) Uani 1 1 d . . . . .
N1 N 0.72001(17) 0.81882(12) 0.02883(7) 0.0249(3) Uani 1 1 d . . . . .
N2 N 0.99389(17) 1.09505(13) -0.11409(7) 0.0268(3) Uani 1 1 d . . . . .
N3 N 0.7962(2) 0.82995(14) 0.21286(8) 0.0328(4) Uani 1 1 d . . . . .
N4 N 0.55397(16) 1.02577(15) -0.11107(8) 0.0301(4) Uani 1 1 d . . . . .
C1 C 1.17282(19) 0.94341(16) 0.06322(8) 0.0241(4) Uani 1 1 d . . . . .
C2 C 1.28043(19) 1.01284(16) 0.02360(10) 0.0288(4) Uani 1 1 d . . . . .
H2A H 1.3123 0.9699 -0.0170 0.035 Uiso 1 1 calc R U . . .
H2B H 1.3646 1.0307 0.0519 0.035 Uiso 1 1 calc R U . . .
C3 C 1.20303(19) 1.12341(15) 0.00314(9) 0.0257(4) Uani 1 1 d . . . . .
H3A H 1.2263 1.1448 -0.0441 0.031 Uiso 1 1 calc R U . . .
H3B H 1.2299 1.1879 0.0334 0.031 Uiso 1 1 calc R U . . .
C4 C 1.04307(18) 1.09491(13) 0.01027(8) 0.0205(3) Uani 1 1 d . . . . .
C5 C 1.03724(18) 1.01547(14) 0.07429(8) 0.0203(3) Uani 1 1 d . . . . .
C6 C 0.90725(18) 0.93488(14) 0.08461(8) 0.0202(3) Uani 1 1 d . . . . .
H6 H 0.9430 0.8686 0.1121 0.024 Uiso 1 1 calc R U . . .
C7 C 0.85829(18) 0.88234(14) 0.01563(8) 0.0193(3) Uani 1 1 d . . . . .
H7 H 0.9313 0.8246 0.0012 0.023 Uiso 1 1 calc R U . . .
C8 C 0.84202(17) 0.97135(14) -0.04136(8) 0.0185(3) Uani 1 1 d . . . . .
H8 H 0.7749 1.0334 -0.0267 0.022 Uiso 1 1 calc R U . . .
C9 C 0.99164(18) 1.02216(14) -0.05059(8) 0.0201(3) Uani 1 1 d . . . . .
H9 H 1.0600 0.9570 -0.0569 0.024 Uiso 1 1 calc R U . . .
C10 C 1.0650(2) 1.08615(17) 0.13921(9) 0.0288(4) Uani 1 1 d . . . . .
H10A H 1.0608 1.0352 0.1787 0.043 Uiso 1 1 calc R U . . .
H10B H 0.9922 1.1463 0.1435 0.043 Uiso 1 1 calc R U . . .
H10C H 1.1594 1.1218 0.1366 0.043 Uiso 1 1 calc R U . . .
C11 C 0.78121(18) 0.98365(14) 0.12367(8) 0.0211(3) Uani 1 1 d . . . . .
C12 C 0.7226(2) 0.92697(15) 0.17970(8) 0.0243(4) Uani 1 1 d . . . . .
C13 C 0.5952(2) 0.95852(17) 0.20980(9) 0.0296(4) Uani 1 1 d . . . . .
H13 H 0.5590 0.9163 0.2472 0.036 Uiso 1 1 calc R U . . .
C14 C 0.5215(2) 1.05218(17) 0.18470(10) 0.0332(4) Uani 1 1 d . . . . .
H14 H 0.4334 1.0746 0.2044 0.040 Uiso 1 1 calc R U . . .
C15 C 0.5771(2) 1.11281(17) 0.13072(10) 0.0306(4) Uani 1 1 d . . . . .
H15 H 0.5276 1.1781 0.1137 0.037 Uiso 1 1 calc R U . . .
C16 C 0.7044(2) 1.07946(15) 0.10110(9) 0.0256(4) Uani 1 1 d . . . . .
H16 H 0.7407 1.1231 0.0643 0.031 Uiso 1 1 calc R U . . .
C17 C 0.78868(18) 0.91768(13) -0.10716(8) 0.0201(3) Uani 1 1 d . . . . .
C18 C 0.65608(19) 0.93931(15) -0.13713(9) 0.0229(3) Uani 1 1 d . . . . .
C19 C 0.6105(2) 0.88120(16) -0.19475(9) 0.0286(4) Uani 1 1 d . . . . .
H19 H 0.5183 0.8954 -0.2127 0.034 Uiso 1 1 calc R U . . .
C20 C 0.6999(2) 0.80287(16) -0.22570(9) 0.0306(4) Uani 1 1 d . . . . .
H20 H 0.6698 0.7633 -0.2653 0.037 Uiso 1 1 calc R U . . .
C21 C 0.8327(2) 0.78239(15) -0.19891(9) 0.0286(4) Uani 1 1 d . . . . .
H21 H 0.8955 0.7301 -0.2208 0.034 Uiso 1 1 calc R U . . .
C22 C 0.87556(19) 0.83781(14) -0.14005(9) 0.0237(3) Uani 1 1 d . . . . .
H22 H 0.9667 0.8208 -0.1216 0.028 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
O1 C1 1.205(2) . ?
O2 C4 1.412(2) . ?
O3 N1 1.225(2) . ?
O4 N1 1.218(2) . ?
O5 N2 1.219(2) . ?
O6 N2 1.221(2) . ?
O7 N3 1.221(2) . ?
O8 N3 1.223(2) . ?
O9 N4 1.215(2) . ?
O10 N4 1.213(2) . ?
N1 C7 1.515(2) . ?
N2 C9 1.513(2) . ?
N3 C12 1.475(2) . ?
N4 C18 1.480(2) . ?
C1 C2 1.511(3) . ?
C1 C5 1.538(2) . ?
C2 C3 1.529(3) . ?
C3 C4 1.543(2) . ?
C4 C9 1.546(2) . ?
C4 C5 1.566(2) . ?
C5 C10 1.544(2) . ?
C5 C6 1.551(2) . ?
C6 C11 1.521(2) . ?
C6 C7 1.562(2) . ?
C7 C8 1.536(2) . ?
C8 C17 1.526(2) . ?
C8 C9 1.534(2) . ?
C11 C16 1.398(2) . ?
C11 C12 1.400(2) . ?
C12 C13 1.384(3) . ?
C13 C14 1.381(3) . ?
C14 C15 1.380(3) . ?
C15 C16 1.385(3) . ?
C17 C22 1.395(2) . ?
C17 C18 1.401(2) . ?
C18 C19 1.390(3) . ?
C19 C20 1.380(3) . ?
C20 C21 1.375(3) . ?
C21 C22 1.388(2) . ?

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 N1 O3 124.63(15) . . ?
O4 N1 C7 119.47(13) . . ?
O3 N1 C7 115.82(15) . . ?
O5 N2 O6 124.26(16) . . ?
O5 N2 C9 118.55(15) . . ?
O6 N2 C9 117.19(15) . . ?
O7 N3 O8 124.66(19) . . ?
O7 N3 C12 117.60(17) . . ?
O8 N3 C12 117.65(18) . . ?
O10 N4 O9 122.31(18) . . ?
O10 N4 C18 117.45(18) . . ?
O9 N4 C18 120.24(15) . . ?
O1 C1 C2 126.13(17) . . ?
O1 C1 C5 124.18(17) . . ?
C2 C1 C5 109.66(15) . . ?
C1 C2 C3 105.50(14) . . ?
C2 C3 C4 104.94(13) . . ?
O2 C4 C3 113.40(13) . . ?
O2 C4 C9 106.98(13) . . ?
C3 C4 C9 110.47(14) . . ?
O2 C4 C5 115.15(14) . . ?
C3 C4 C5 103.53(13) . . ?
C9 C4 C5 107.17(12) . . ?
C1 C5 C10 105.53(13) . . ?
C1 C5 C6 109.95(13) . . ?
C10 C5 C6 110.12(14) . . ?
C1 C5 C4 100.17(13) . . ?
C10 C5 C4 110.58(13) . . ?
C6 C5 C4 119.27(13) . . ?
C11 C6 C5 116.98(13) . . ?
C11 C6 C7 111.04(13) . . ?
C5 C6 C7 110.63(13) . . ?
N1 C7 C8 111.62(13) . . ?
N1 C7 C6 106.97(13) . . ?
C8 C7 C6 113.95(13) . . ?
C17 C8 C9 110.86(13) . . ?
C17 C8 C7 112.48(13) . . ?
C9 C8 C7 104.77(13) . . ?
N2 C9 C8 109.05(13) . . ?
N2 C9 C4 109.55(12) . . ?
C8 C9 C4 113.79(13) . . ?
C16 C11 C12 115.03(16) . . ?
C16 C11 C6 122.35(15) . . ?
C12 C11 C6 122.11(15) . . ?
C13 C12 C11 123.68(17) . . ?
C13 C12 N3 114.57(16) . . ?
C11 C12 N3 121.72(16) . . ?
C14 C13 C12 119.13(18) . . ?
C15 C14 C13 119.29(18) . . ?
C14 C15 C16 120.66(18) . . ?
C15 C16 C11 122.15(18) . . ?
C22 C17 C18 116.21(15) . . ?
C22 C17 C8 118.44(15) . . ?
C18 C17 C8 125.32(15) . . ?
C19 C18 C17 122.14(17) . . ?
C19 C18 N4 114.50(16) . . ?
C17 C18 N4 123.36(15) . . ?
C20 C19 C18 119.71(18) . . ?
C21 C20 C19 119.64(16) . . ?
C20 C21 C22 120.31(17) . . ?
C21 C22 C17 121.92(17) . . ?

_refine_diff_density_max         0.224
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.032

####################################################################### 
# 
# 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_3i_third_crystal_ic18028_1
_database_code_depnum_ccdc_archive 'CCDC 1488808'
_audit_update_record             
;
2016-09-23 deposited with the CCDC.
2016-09-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        3i
_chemical_name_common            'third crystal ic18028-1'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H20 N4 O10'
_chemical_formula_weight         500.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   9.38810(10)
_cell_length_b                   11.6070(2)
_cell_length_c                   19.7468(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2151.76(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9904
_cell_measurement_theta_min      4.42
_cell_measurement_theta_max      70.03

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.333
_exptl_crystal_size_mid          0.298
_exptl_crystal_size_min          0.157
_exptl_absorpt_coefficient_mu    1.064
_shelx_estimated_absorpt_T_min   0.718
_shelx_estimated_absorpt_T_max   0.851
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5782
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10354
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.418
_diffrn_reflns_theta_max         69.931
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4066
_reflns_number_gt                3979
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.748
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0344P)²+0.3914P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0034(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1686 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.06(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4066
_refine_ls_number_parameters     328
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0247
_refine_ls_wR_factor_ref         0.0634
_refine_ls_wR_factor_gt          0.0629
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
O1 O 1.18722(16) 0.84539(12) 0.08221(7) 0.0342(3) Uani 1 1 d . . . . .
O2 O 0.95549(14) 1.19360(10) 0.01314(7) 0.0262(3) Uani 1 1 d . . . . .
H2 H 0.9958 1.2447 0.0364 0.039 Uiso 1 1 calc R U . . .
O3 O 0.72978(17) 0.73118(11) 0.06300(7) 0.0348(3) Uani 1 1 d . . . . .
O4 O 0.60844(14) 0.85899(12) 0.00805(7) 0.0317(3) Uani 1 1 d . . . . .
O5 O 0.88868(16) 1.15156(12) -0.12819(7) 0.0335(3) Uani 1 1 d . . . . .
O6 O 1.10297(17) 1.09329(15) -0.14797(7) 0.0413(4) Uani 1 1 d . . . . .
O7 O 0.91928(18) 0.84498(16) 0.23079(8) 0.0464(4) Uani 1 1 d . . . . .
O8 O 0.7279(2) 0.74210(15) 0.22314(10) 0.0549(5) Uani 1 1 d . . . . .
O9 O 0.59537(17) 1.10430(13) -0.07540(9) 0.0442(4) Uani 1 1 d . . . . .
O10 O 0.42971(17) 1.0150(2) -0.12704(10) 0.0646(6) Uani 1 1 d . . . . .
N1 N 0.72005(17) 0.81873(12) 0.02893(7) 0.0243(3) Uani 1 1 d . . . . .
N2 N 0.99397(17) 1.09503(13) -0.11412(8) 0.0267(3) Uani 1 1 d . . . . .
N3 N 0.7961(2) 0.82992(14) 0.21285(8) 0.0323(4) Uani 1 1 d . . . . .
N4 N 0.55406(17) 1.02569(15) -0.11110(8) 0.0295(4) Uani 1 1 d . . . . .
C1 C 1.1731(2) 0.94325(16) 0.06322(9) 0.0239(4) Uani 1 1 d . . . . .
C2 C 1.28032(19) 1.01290(17) 0.02348(10) 0.0287(4) Uani 1 1 d . . . . .
H2A H 1.3121 0.9700 -0.0171 0.034 Uiso 1 1 calc R U . . .
H2B H 1.3646 1.0308 0.0517 0.034 Uiso 1 1 calc R U . . .
C3 C 1.20315(19) 1.12329(15) 0.00308(9) 0.0258(4) Uani 1 1 d . . . . .
H3A H 1.2265 1.1447 -0.0442 0.031 Uiso 1 1 calc R U . . .
H3B H 1.2300 1.1877 0.0333 0.031 Uiso 1 1 calc R U . . .
C4 C 1.04311(18) 1.09487(14) 0.01020(9) 0.0204(3) Uani 1 1 d . . . . .
C5 C 1.03724(18) 1.01553(14) 0.07425(8) 0.0201(3) Uani 1 1 d . . . . .
C6 C 0.90720(18) 0.93484(14) 0.08460(8) 0.0198(3) Uani 1 1 d . . . . .
H6 H 0.9430 0.8685 0.1121 0.024 Uiso 1 1 calc R U . . .
C7 C 0.85849(18) 0.88226(14) 0.01558(9) 0.0193(3) Uani 1 1 d . . . . .
H7 H 0.9315 0.8245 0.0011 0.023 Uiso 1 1 calc R U . . .
C8 C 0.84213(17) 0.97141(14) -0.04138(8) 0.0184(3) Uani 1 1 d . . . . .
H8 H 0.7750 1.0334 -0.0267 0.022 Uiso 1 1 calc R U . . .
C9 C 0.99168(18) 1.02221(14) -0.05066(8) 0.0200(3) Uani 1 1 d . . . . .
H9 H 1.0599 0.9570 -0.0570 0.024 Uiso 1 1 calc R U . . .
C10 C 1.0650(2) 1.08614(17) 0.13924(9) 0.0284(4) Uani 1 1 d . . . . .
H10A H 1.0601 1.0352 0.1788 0.043 Uiso 1 1 calc R U . . .
H10B H 0.9927 1.1467 0.1434 0.043 Uiso 1 1 calc R U . . .
H10C H 1.1597 1.1213 0.1368 0.043 Uiso 1 1 calc R U . . .
C11 C 0.78110(18) 0.98360(14) 0.12371(8) 0.0208(3) Uani 1 1 d . . . . .
C12 C 0.7225(2) 0.92692(16) 0.17972(9) 0.0242(4) Uani 1 1 d . . . . .
C13 C 0.5948(2) 0.95853(17) 0.20984(10) 0.0291(4) Uani 1 1 d . . . . .
H13 H 0.5584 0.9163 0.2472 0.035 Uiso 1 1 calc R U . . .
C14 C 0.5216(2) 1.05215(18) 0.18469(11) 0.0331(4) Uani 1 1 d . . . . .
H14 H 0.4335 1.0747 0.2044 0.040 Uiso 1 1 calc R U . . .
C15 C 0.5773(2) 1.11285(17) 0.13065(11) 0.0305(4) Uani 1 1 d . . . . .
H15 H 0.5278 1.1781 0.1136 0.037 Uiso 1 1 calc R U . . .
C16 C 0.7046(2) 1.07950(15) 0.10109(9) 0.0249(4) Uani 1 1 d . . . . .
H16 H 0.7411 1.1232 0.0643 0.030 Uiso 1 1 calc R U . . .
C17 C 0.78878(18) 0.91759(14) -0.10723(8) 0.0198(3) Uani 1 1 d . . . . .
C18 C 0.65604(19) 0.93925(15) -0.13718(9) 0.0226(3) Uani 1 1 d . . . . .
C19 C 0.6107(2) 0.88114(17) -0.19476(10) 0.0281(4) Uani 1 1 d . . . . .
H19 H 0.5185 0.8953 -0.2128 0.034 Uiso 1 1 calc R U . . .
C20 C 0.6998(2) 0.80281(17) -0.22570(9) 0.0304(4) Uani 1 1 d . . . . .
H20 H 0.6697 0.7632 -0.2653 0.037 Uiso 1 1 calc R U . . .
C21 C 0.8328(2) 0.78240(16) -0.19887(9) 0.0281(4) Uani 1 1 d . . . . .
H21 H 0.8956 0.7301 -0.2208 0.034 Uiso 1 1 calc R U . . .
C22 C 0.87560(19) 0.83778(15) -0.14010(9) 0.0233(3) Uani 1 1 d . . . . .
H22 H 0.9667 0.8209 -0.1217 0.028 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
O1 C1 1.204(2) . ?
O2 C4 1.412(2) . ?
O3 N1 1.222(2) . ?
O4 N1 1.219(2) . ?
O5 N2 1.219(2) . ?
O6 N2 1.222(2) . ?
O7 N3 1.222(2) . ?
O8 N3 1.221(3) . ?
O9 N4 1.217(2) . ?
O10 N4 1.215(2) . ?
N1 C7 1.517(2) . ?
N2 C9 1.512(2) . ?
N3 C12 1.474(2) . ?
N4 C18 1.479(2) . ?
C1 C2 1.511(3) . ?
C1 C5 1.542(2) . ?
C2 C3 1.526(3) . ?
C3 C4 1.545(2) . ?
C4 C9 1.545(2) . ?
C4 C5 1.566(2) . ?
C5 C10 1.545(2) . ?
C5 C6 1.552(2) . ?
C6 C11 1.523(2) . ?
C6 C7 1.562(2) . ?
C7 C8 1.536(2) . ?
C8 C17 1.527(2) . ?
C8 C9 1.534(2) . ?
C11 C16 1.398(3) . ?
C11 C12 1.400(2) . ?
C12 C13 1.388(3) . ?
C13 C14 1.379(3) . ?
C14 C15 1.382(3) . ?
C15 C16 1.386(3) . ?
C17 C22 1.394(3) . ?
C17 C18 1.402(2) . ?
C18 C19 1.389(3) . ?
C19 C20 1.378(3) . ?
C20 C21 1.377(3) . ?
C21 C22 1.386(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
O4 N1 O3 124.69(15) . . ?
O4 N1 C7 119.41(14) . . ?
O3 N1 C7 115.83(15) . . ?
O5 N2 O6 124.28(16) . . ?
O5 N2 C9 118.59(15) . . ?
O6 N2 C9 117.13(16) . . ?
O8 N3 O7 124.61(19) . . ?
O8 N3 C12 117.72(18) . . ?
O7 N3 C12 117.58(17) . . ?
O10 N4 O9 122.19(18) . . ?
O10 N4 C18 117.54(18) . . ?
O9 N4 C18 120.27(15) . . ?
O1 C1 C2 126.38(17) . . ?
O1 C1 C5 124.11(17) . . ?
C2 C1 C5 109.48(15) . . ?
C1 C2 C3 105.66(14) . . ?
C2 C3 C4 104.98(14) . . ?
O2 C4 C3 113.40(14) . . ?
O2 C4 C9 107.04(13) . . ?
C3 C4 C9 110.47(14) . . ?
O2 C4 C5 115.07(14) . . ?
C3 C4 C5 103.49(13) . . ?
C9 C4 C5 107.23(12) . . ?
C1 C5 C10 105.47(14) . . ?
C1 C5 C6 109.93(14) . . ?
C10 C5 C6 110.08(14) . . ?
C1 C5 C4 100.18(13) . . ?
C10 C5 C4 110.68(13) . . ?
C6 C5 C4 119.27(13) . . ?
C11 C6 C5 117.00(14) . . ?
C11 C6 C7 111.11(14) . . ?
C5 C6 C7 110.56(13) . . ?
N1 C7 C8 111.66(13) . . ?
N1 C7 C6 106.80(13) . . ?
C8 C7 C6 113.90(13) . . ?
C17 C8 C9 110.85(14) . . ?
C17 C8 C7 112.38(13) . . ?
C9 C8 C7 104.77(13) . . ?
N2 C9 C8 109.09(13) . . ?
N2 C9 C4 109.57(13) . . ?
C8 C9 C4 113.76(14) . . ?
C16 C11 C12 115.16(16) . . ?
C16 C11 C6 122.23(16) . . ?
C12 C11 C6 122.11(15) . . ?
C13 C12 C11 123.63(18) . . ?
C13 C12 N3 114.64(16) . . ?
C11 C12 N3 121.70(16) . . ?
C14 C13 C12 119.02(18) . . ?
C13 C14 C15 119.43(18) . . ?
C14 C15 C16 120.63(19) . . ?
C15 C16 C11 122.07(18) . . ?
C22 C17 C18 116.25(15) . . ?
C22 C17 C8 118.46(15) . . ?
C18 C17 C8 125.26(15) . . ?
C19 C18 C17 122.06(17) . . ?
C19 C18 N4 114.56(16) . . ?
C17 C18 N4 123.37(16) . . ?
C20 C19 C18 119.80(18) . . ?
C21 C20 C19 119.56(17) . . ?
C20 C21 C22 120.35(18) . . ?
C21 C22 C17 121.90(17) . . ?

_refine_diff_density_max         0.213
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.031

####################################################################### 
# 
# 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_5a_ic18058-1
_database_code_depnum_ccdc_archive 'CCDC 1495243'
_audit_update_record             
;
2016-09-23 deposited with the CCDC.
2016-09-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        5a
_chemical_name_common            ic18058-1
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H22 N2 O6'
_chemical_formula_weight         410.41

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   6.60530(10)
_cell_length_b                   16.3208(3)
_cell_length_c                   18.4301(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1986.83(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9909
_cell_measurement_theta_min      3.62
_cell_measurement_theta_max      70.19

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.506
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.065
_exptl_absorpt_coefficient_mu    0.838
_shelx_estimated_absorpt_T_min   0.676
_shelx_estimated_absorpt_T_max   0.948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5874
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9468
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.617
_diffrn_reflns_theta_max         69.976
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3755
_reflns_number_gt                3652
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.997

_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0461P)²+0.3152P] 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_abs_structure_details 
; 
 Flack x determined using 1508 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.52(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3755
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0318
_refine_ls_wR_factor_ref         0.0800
_refine_ls_wR_factor_gt          0.0793
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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
O1 O 0.3977(2) 0.92750(10) 0.19721(8) 0.0355(3) Uani 1 1 d . . . . .
O2 O 1.07391(19) 1.01133(8) 0.25854(6) 0.0246(3) Uani 1 1 d . . . . .
H2 H 1.1456 0.9839 0.2298 0.037 Uiso 1 1 calc R U . . .
O3 O 0.5496(2) 1.01506(10) 0.07269(8) 0.0372(3) Uani 1 1 d . . . . .
O4 O 0.6566(3) 0.95843(11) -0.02609(8) 0.0490(5) Uani 1 1 d . . . . .
O5 O 0.9086(3) 1.21323(9) 0.20039(10) 0.0517(5) Uani 1 1 d . . . . .
O6 O 1.1908(3) 1.15456(10) 0.16947(9) 0.0448(4) Uani 1 1 d . . . . .
N1 N 0.6780(3) 0.97837(10) 0.03728(8) 0.0292(4) Uani 1 1 d . . . . .
N2 N 1.0082(3) 1.15467(10) 0.17769(9) 0.0329(4) Uani 1 1 d . . . . .
C1 C 0.5431(3) 0.96581(12) 0.21782(9) 0.0253(4) Uani 1 1 d . . . . .
C2 C 0.5302(3) 1.04331(14) 0.26302(12) 0.0352(5) Uani 1 1 d . . . . .
H2A H 0.4432 1.0344 0.3060 0.042 Uiso 1 1 calc R U . . .
H2B H 0.4729 1.0888 0.2340 0.042 Uiso 1 1 calc R U . . .
C3 C 0.7458(3) 1.06310(12) 0.28615(10) 0.0275(4) Uani 1 1 d . . . . .
H3A H 0.7747 1.0402 0.3348 0.033 Uiso 1 1 calc R U . . .
H3B H 0.7678 1.1231 0.2875 0.033 Uiso 1 1 calc R U . . .
C4 C 0.8809(3) 1.02293(11) 0.22836(9) 0.0210(3) Uani 1 1 d . . . . .
C5 C 0.7663(3) 0.94134(11) 0.21001(9) 0.0209(3) Uani 1 1 d . . . . .
C6 C 0.8473(3) 0.90060(10) 0.13973(9) 0.0211(4) Uani 1 1 d . . . . .
H6 H 0.9900 0.8866 0.1529 0.025 Uiso 1 1 calc R U . . .
C7 C 0.8745(3) 0.95766(11) 0.07408(9) 0.0230(4) Uani 1 1 d . . . . .
H7 H 0.9595 0.9277 0.0379 0.028 Uiso 1 1 calc R U . . .
C8 C 0.9871(3) 1.03757(10) 0.09293(9) 0.0232(4) Uani 1 1 d . . . . .
H8 H 1.1281 1.0219 0.1070 0.028 Uiso 1 1 calc R U . . .
C9 C 0.8907(3) 1.07802(11) 0.15933(9) 0.0230(4) Uani 1 1 d . . . . .
H9 H 0.7495 1.0944 0.1463 0.028 Uiso 1 1 calc R U . . .
C10 C 0.7970(3) 0.87945(12) 0.27260(10) 0.0294(4) Uani 1 1 d . . . . .
H10A H 0.7557 0.9047 0.3185 0.044 Uiso 1 1 calc R U . . .
H10B H 0.9402 0.8639 0.2753 0.044 Uiso 1 1 calc R U . . .
H10C H 0.7147 0.8305 0.2636 0.044 Uiso 1 1 calc R U . . .
C11 C 0.7581(3) 0.81735(11) 0.11920(9) 0.0244(4) Uani 1 1 d . . . . .
C12 C 0.5654(3) 0.80692(12) 0.08994(10) 0.0306(4) Uani 1 1 d . . . . .
H12 H 0.4817 0.8534 0.0818 0.037 Uiso 1 1 calc R U . . .
C13 C 0.4942(4) 0.72922(13) 0.07248(11) 0.0367(5) Uani 1 1 d . . . . .
H13 H 0.3629 0.7228 0.0522 0.044 Uiso 1 1 calc R U . . .
C14 C 0.6149(4) 0.66103(12) 0.08465(11) 0.0397(5) Uani 1 1 d . . . . .
H14 H 0.5652 0.6079 0.0736 0.048 Uiso 1 1 calc R U . . .
C15 C 0.8066(4) 0.67031(13) 0.11274(11) 0.0405(5) Uani 1 1 d . . . . .
H15 H 0.8896 0.6236 0.1207 0.049 Uiso 1 1 calc R U . . .
C16 C 0.8786(3) 0.74811(11) 0.12943(10) 0.0300(4) Uani 1 1 d . . . . .
H16 H 1.0119 0.7542 0.1481 0.036 Uiso 1 1 calc R U . . .
C17 C 1.0041(3) 1.09324(12) 0.02673(10) 0.0271(4) Uani 1 1 d . . . . .
C18 C 1.1571(3) 1.07854(15) -0.02315(11) 0.0363(5) Uani 1 1 d . . . . .
H18 H 1.2501 1.0351 -0.0150 0.044 Uiso 1 1 calc R U . . .
C19 C 1.1755(4) 1.12702(18) -0.08505(12) 0.0479(6) Uani 1 1 d . . . . .
H19 H 1.2806 1.1164 -0.1190 0.057 Uiso 1 1 calc R U . . .
C20 C 1.0410(4) 1.19048(16) -0.09715(12) 0.0486(7) Uani 1 1 d . . . . .
H20 H 1.0540 1.2238 -0.1392 0.058 Uiso 1 1 calc R U . . .
C21 C 0.8890(5) 1.20519(14) -0.04829(13) 0.0480(6) Uani 1 1 d . . . . .
H21 H 0.7965 1.2487 -0.0566 0.058 Uiso 1 1 calc R U . . .
C22 C 0.8695(4) 1.15675(13) 0.01332(12) 0.0394(5) Uani 1 1 d . . . . .
H22 H 0.7629 1.1672 0.0466 0.047 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
O1 C1 1.208(2) . ?
O2 C4 1.404(2) . ?
O3 N1 1.226(2) . ?
O4 N1 1.221(2) . ?
O5 N2 1.233(3) . ?
O6 N2 1.216(3) . ?
N1 C7 1.504(2) . ?
N2 C9 1.510(2) . ?
C1 C2 1.517(3) . ?
C1 C5 1.534(2) . ?
C2 C3 1.521(3) . ?
C3 C4 1.536(2) . ?
C4 C9 1.559(2) . ?
C4 C5 1.568(2) . ?
C5 C10 1.547(2) . ?
C5 C6 1.551(2) . ?
C6 C11 1.529(2) . ?
C6 C7 1.537(2) . ?
C7 C8 1.541(2) . ?
C8 C17 1.525(2) . ?
C8 C9 1.529(2) . ?
C11 C12 1.393(3) . ?
C11 C16 1.395(3) . ?
C12 C13 1.390(3) . ?
C13 C14 1.387(3) . ?
C14 C15 1.376(4) . ?
C15 C16 1.391(3) . ?
C17 C22 1.387(3) . ?
C17 C18 1.388(3) . ?
C18 C19 1.394(3) . ?
C19 C20 1.382(4) . ?
C20 C21 1.370(4) . ?
C21 C22 1.390(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
O4 N1 O3 124.04(19) . . ?
O4 N1 C7 118.13(18) . . ?
O3 N1 C7 117.83(14) . . ?
O6 N2 O5 124.94(19) . . ?
O6 N2 C9 118.70(18) . . ?
O5 N2 C9 116.35(19) . . ?
O1 C1 C2 124.05(17) . . ?
O1 C1 C5 126.88(16) . . ?
C2 C1 C5 108.82(15) . . ?
C1 C2 C3 106.17(15) . . ?
C2 C3 C4 104.99(14) . . ?
O2 C4 C3 108.07(13) . . ?
O2 C4 C9 111.28(14) . . ?
C3 C4 C9 110.11(15) . . ?
O2 C4 C5 114.15(14) . . ?
C3 C4 C5 103.39(14) . . ?
C9 C4 C5 109.51(13) . . ?
C1 C5 C10 103.07(15) . . ?
C1 C5 C6 121.43(15) . . ?
C10 C5 C6 107.31(14) . . ?
C1 C5 C4 102.85(14) . . ?
C10 C5 C4 109.29(14) . . ?
C6 C5 C4 112.18(14) . . ?
C11 C6 C7 112.87(13) . . ?
C11 C6 C5 117.06(15) . . ?
C7 C6 C5 115.97(14) . . ?
N1 C7 C6 112.97(15) . . ?
N1 C7 C8 109.15(14) . . ?
C6 C7 C8 113.06(14) . . ?
C17 C8 C9 114.42(15) . . ?
C17 C8 C7 111.06(14) . . ?
C9 C8 C7 110.19(14) . . ?
N2 C9 C8 108.86(15) . . ?
N2 C9 C4 108.45(13) . . ?
C8 C9 C4 114.92(14) . . ?
C12 C11 C16 118.35(18) . . ?
C12 C11 C6 123.83(17) . . ?
C16 C11 C6 117.81(17) . . ?
C13 C12 C11 120.7(2) . . ?
C14 C13 C12 120.0(2) . . ?
C15 C14 C13 120.1(2) . . ?
C14 C15 C16 119.9(2) . . ?
C15 C16 C11 121.0(2) . . ?
C22 C17 C18 118.55(18) . . ?
C22 C17 C8 122.71(18) . . ?
C18 C17 C8 118.72(18) . . ?
C17 C18 C19 120.5(2) . . ?
C20 C19 C18 120.1(2) . . ?
C21 C20 C19 119.7(2) . . ?
C20 C21 C22 120.4(2) . . ?
C17 C22 C21 120.7(2) . . ?

_refine_diff_density_max         0.151
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.052

