# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_nsqem_0m
_database_code_depnum_ccdc_archive 'CCDC 1032668'
_audit_update_record             
;
2015-03-01 deposited with the CCDC.
2015-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C52 H67 Cd3 N16 O24'
_chemical_formula_weight         1637.42

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'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   46.64(7)
_cell_length_b                   12.447(18)
_cell_length_c                   31.37(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 131.263(12)
_cell_angle_gamma                90.00
_cell_volume                     13692(33)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1089
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      19.93

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             6616
_exptl_absorpt_coefficient_mu    1.009
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.470
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   'Bruker SADABS (Bruker, 1999)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'Phi and Omega Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17426
_diffrn_reflns_av_R_equivalents  0.0981
_diffrn_reflns_av_sigmaI/netI    0.1136
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.16
_diffrn_reflns_theta_max         20.55
_reflns_number_total             6718
_reflns_number_gt                4336
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker ApexII'
_computing_cell_refinement       'Bruker Apex II'
_computing_data_reduction        'Bruker Apex II'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.1650P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6718
_refine_ls_number_parameters     689
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1234
_refine_ls_R_factor_gt           0.0898
_refine_ls_wR_factor_ref         0.2685
_refine_ls_wR_factor_gt          0.2432
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cd1 Cd 0.37754(4) -0.37393(10) 0.39546(5) 0.0193(4) Uani 1 1 d . . .
Cd2 Cd 0.08689(3) -0.53199(10) 0.07084(5) 0.0198(4) Uani 1 1 d . . .
Cd3 Cd 0.13959(3) -0.19511(10) 0.12080(5) 0.0194(4) Uani 1 1 d . . .
C1A C 0.0580(6) -0.5533(15) -0.0550(8) 0.034(5) Uiso 1 1 d . . .
H1A H 0.0349 -0.5409 -0.0639 0.041 Uiso 1 1 calc R . .
C1B C 0.1253(6) -0.5710(14) 0.2033(8) 0.031(5) Uani 1 1 d . . .
H1B H 0.1468 -0.5842 0.2078 0.037 Uiso 1 1 calc R . .
C1C C 0.3461(5) -0.3485(15) 0.2699(8) 0.030(5) Uani 1 1 d . . .
H1C H 0.3290 -0.3036 0.2672 0.036 Uiso 1 1 calc R . .
C1D C 0.2361(6) -0.5237(18) 0.1002(10) 0.048(6) Uani 1 1 d . . .
H1D H 0.2379 -0.5075 0.1308 0.058 Uiso 1 1 calc R . .
C1E C 0.1615(5) -0.4505(15) 0.1432(7) 0.017(4) Uiso 1 1 d . . .
C1F C 0.4382(5) -0.5976(15) 0.4715(7) 0.020(4) Uiso 1 1 d . . .
C2A C 0.0581(5) -0.570(2) -0.0998(8) 0.056(7) Uani 1 1 d . . .
H2A H 0.0354 -0.5653 -0.1373 0.067 Uiso 1 1 calc R . .
C2B C 0.1280(6) -0.5874(17) 0.2513(9) 0.040(6) Uani 1 1 d . . .
H2B H 0.1509 -0.6066 0.2866 0.048 Uiso 1 1 calc R . .
C2C C 0.3404(5) -0.3680(15) 0.2214(8) 0.032(5) Uani 1 1 d . . .
H2C H 0.3205 -0.3340 0.1877 0.039 Uiso 1 1 calc R . .
C2D C 0.2386(5) -0.4421(17) 0.0737(8) 0.039(6) Uani 1 1 d . . .
H2D H 0.2417 -0.3718 0.0862 0.047 Uiso 1 1 calc R . .
C2E C 0.2034(5) -0.4206(16) 0.1868(7) 0.034(5) Uani 1 1 d . . .
H2E1 H 0.2061 -0.3627 0.2099 0.040 Uiso 1 1 calc R . .
H2E2 H 0.2111 -0.3926 0.1668 0.040 Uiso 1 1 calc R . .
C2F C 0.4740(5) -0.5862(16) 0.5326(8) 0.037(5) Uani 1 1 d . . .
H2F1 H 0.4669 -0.5822 0.5556 0.044 Uiso 1 1 calc R . .
H2F2 H 0.4863 -0.5190 0.5372 0.044 Uiso 1 1 calc R . .
C3A C 0.0928(5) -0.5928(15) -0.0873(7) 0.026(5) Uiso 1 1 d . . .
C3B C 0.0954(6) -0.5738(17) 0.2430(8) 0.043(6) Uani 1 1 d . . .
C3C C 0.3644(5) -0.4388(14) 0.2225(7) 0.021(4) Uani 1 1 d . . .
C3D C 0.2365(5) -0.4632(15) 0.0268(7) 0.024(5) Uani 1 1 d . . .
C3E C 0.2315(5) -0.5104(13) 0.2268(7) 0.020(4) Uani 1 1 d . . .
H3E1 H 0.2232 -0.5426 0.2452 0.024 Uiso 1 1 calc R . .
H3E2 H 0.2310 -0.5657 0.2046 0.024 Uiso 1 1 calc R . .
C3F C 0.5041(5) -0.6821(15) 0.5561(8) 0.037(5) Uani 1 1 d . . .
H3F1 H 0.5255 -0.6714 0.5962 0.044 Uiso 1 1 calc R . .
H3F2 H 0.4921 -0.7499 0.5516 0.044 Uiso 1 1 calc R . .
C4A C 0.1269(5) -0.5985(15) -0.0295(8) 0.033(5) Uani 1 1 d . . .
H4A H 0.1504 -0.6131 -0.0189 0.039 Uiso 1 1 calc R . .
C4B C 0.0627(6) -0.5393(17) 0.1914(9) 0.049(6) Uani 1 1 d . . .
H4B H 0.0406 -0.5288 0.1856 0.059 Uiso 1 1 calc R . .
C4C C 0.3956(5) -0.4821(14) 0.2749(7) 0.021(4) Uiso 1 1 d . . .
H4C H 0.4133 -0.5252 0.2782 0.026 Uiso 1 1 calc R . .
C4D C 0.2317(5) -0.5702(16) 0.0110(9) 0.040(6) Uani 1 1 d . . .
H4D H 0.2294 -0.5883 -0.0199 0.048 Uiso 1 1 calc R . .
C4E C 0.2721(4) -0.4700(13) 0.2718(7) 0.021(4) Uani 1 1 d . . .
H4E1 H 0.2806 -0.4406 0.2531 0.025 Uiso 1 1 calc R . .
H4E2 H 0.2721 -0.4119 0.2924 0.025 Uiso 1 1 calc R . .
C4F C 0.5187(5) -0.6863(14) 0.5235(7) 0.025(5) Uiso 1 1 d . . .
H4F1 H 0.4969 -0.6892 0.4831 0.030 Uiso 1 1 calc R . .
H4F2 H 0.5326 -0.6207 0.5310 0.030 Uiso 1 1 calc R . .
C5A C 0.1230(5) -0.5805(15) 0.0115(7) 0.026(5) Uani 1 1 d . . .
H5A H 0.1449 -0.5869 0.0495 0.031 Uiso 1 1 calc R . .
C5B C 0.0628(5) -0.5198(17) 0.1471(8) 0.037(5) Uani 1 1 d . . .
H5B H 0.0407 -0.4935 0.1128 0.045 Uiso 1 1 calc R . .
C5C C 0.3994(5) -0.4597(15) 0.3207(8) 0.032(5) Uiso 1 1 d . . .
H5C H 0.4196 -0.4921 0.3548 0.038 Uiso 1 1 calc R . .
C5D C 0.2302(5) -0.6523(17) 0.0404(9) 0.040(6) Uani 1 1 d . . .
H5D H 0.2286 -0.7236 0.0301 0.048 Uiso 1 1 calc R . .
C5E C 0.3003(5) -0.5535(15) 0.3137(7) 0.022(4) Uiso 1 1 d . . .
C5F C 0.5437(6) -0.7795(16) 0.5393(8) 0.031(5) Uani 1 1 d . . .
C6A C 0.0920(6) -0.6150(17) -0.1335(8) 0.037(5) Uani 1 1 d . . .
H6A H 0.0693 -0.6072 -0.1708 0.044 Uiso 1 1 calc R . .
C6B C 0.0937(6) -0.5942(17) 0.2881(8) 0.038(5) Uani 1 1 d . . .
H6B H 0.0736 -0.5694 0.2849 0.046 Uiso 1 1 calc R . .
C6C C 0.3579(6) -0.4619(17) 0.1705(9) 0.043(6) Uani 1 1 d . . .
H6C H 0.3371 -0.4309 0.1364 0.052 Uiso 1 1 calc R . .
C6D C 0.2407(5) -0.3825(15) -0.0019(8) 0.031(5) Uani 1 1 d . . .
H6D H 0.2365 -0.4000 -0.0344 0.038 Uiso 1 1 calc R . .
C7A C 0.1462(5) -0.6983(14) -0.1649(7) 0.022(4) Uiso 1 1 d . . .
H7A H 0.1695 -0.7040 -0.1280 0.027 Uiso 1 1 calc R . .
C7B C 0.1440(5) -0.7170(17) 0.4163(8) 0.039(6) Uani 1 1 d . . .
H7B H 0.1646 -0.7399 0.4201 0.046 Uiso 1 1 calc R . .
C7C C 0.3946(6) -0.5824(18) 0.1211(9) 0.046(6) Uani 1 1 d . . .
H7C H 0.4165 -0.6077 0.1560 0.055 Uiso 1 1 calc R . .
C8A C 0.1735(5) -0.7812(15) -0.2492(8) 0.030(5) Uani 1 1 d . . .
H8A H 0.1959 -0.7998 -0.2412 0.036 Uiso 1 1 calc R . .
C8B C 0.1139(6) -0.2715(15) 0.0029(9) 0.039(6) Uani 1 1 d . . .
H8B H 0.0941 -0.2979 0.0000 0.046 Uiso 1 1 calc R . .
C8C C 0.4168(5) -0.3603(15) 0.5272(8) 0.033(5) Uani 1 1 d . . .
H8C H 0.4382 -0.3444 0.5317 0.040 Uiso 1 1 calc R . .
C9A C 0.1755(5) -0.7555(16) -0.2025(8) 0.034(5) Uani 1 1 d . . .
H9A H 0.1985 -0.7592 -0.1653 0.040 Uiso 1 1 calc R . .
C9B C 0.1138(6) -0.2928(17) -0.0413(8) 0.043(6) Uani 1 1 d . . .
H9B H 0.0937 -0.3308 -0.0731 0.052 Uiso 1 1 calc R . .
C9C C 0.4210(6) -0.3709(15) 0.5746(8) 0.034(5) Uani 1 1 d . . .
H9C H 0.4448 -0.3594 0.6103 0.041 Uiso 1 1 calc R . .
C10A C 0.1430(5) -0.7257(15) -0.2140(8) 0.026(5) Uani 1 1 d . . .
C10B C 0.1432(5) -0.2581(16) -0.0381(8) 0.032(5) Uani 1 1 d . . .
C10C C 0.3898(5) -0.3990(16) 0.5696(8) 0.031(5) Uani 1 1 d . . .
C11A C 0.1091(5) -0.7211(14) -0.2713(7) 0.026(5) Uani 1 1 d . . .
H11A H 0.0866 -0.6987 -0.2804 0.031 Uiso 1 1 calc R . .
C11B C 0.1727(5) -0.1990(16) 0.0093(8) 0.032(5) Uani 1 1 d . . .
H11B H 0.1930 -0.1730 0.0131 0.039 Uiso 1 1 calc R . .
C11C C 0.3554(5) -0.4129(16) 0.5147(8) 0.032(5) Uani 1 1 d . . .
H11C H 0.3338 -0.4308 0.5091 0.039 Uiso 1 1 calc R . .
C12A C 0.1087(5) -0.7496(15) -0.3146(8) 0.030(5) Uani 1 1 d . . .
H12A H 0.0858 -0.7480 -0.3520 0.035 Uiso 1 1 calc R . .
C12B C 0.1705(5) -0.1812(14) 0.0502(7) 0.024(5) Uani 1 1 d . . .
H12B H 0.1904 -0.1426 0.0820 0.029 Uiso 1 1 calc R . .
C12C C 0.3527(5) -0.4014(14) 0.4709(8) 0.027(5) Uiso 1 1 d . . .
H12C H 0.3291 -0.4138 0.4352 0.032 Uiso 1 1 calc R . .
N1A N 0.0906(4) -0.5554(11) 0.0004(6) 0.022(4) Uani 1 1 d . . .
N1B N 0.0929(4) -0.5372(11) 0.1519(6) 0.024(4) Uiso 1 1 d . . .
N1C N 0.3757(4) -0.3922(11) 0.3217(6) 0.018(3) Uiso 1 1 d . . .
N1D N 0.2310(5) -0.6293(13) 0.0832(7) 0.037(4) Uani 1 1 d . . .
N1N N 0.4823(7) -0.705(2) 0.3622(12) 0.102(9) Uiso 1 1 d . . .
N2A N 0.1218(5) -0.6447(13) -0.1241(6) 0.033(4) Uani 1 1 d . . .
N2B N 0.1220(5) -0.6488(15) 0.3324(7) 0.047(5) Uani 1 1 d . . .
N2C N 0.3799(5) -0.5232(14) 0.1714(6) 0.047(5) Uani 1 1 d . . .
N2D N 0.2503(5) -0.2852(14) 0.0181(7) 0.039(4) Uani 1 1 d . . .
N2N N 0.2572(5) -0.9932(17) 0.1172(7) 0.049(5) Uani 1 1 d . . .
N3A N 0.1151(4) -0.6651(12) -0.1745(6) 0.028(4) Uiso 1 1 d . . .
N3B N 0.1171(5) -0.6647(14) 0.3723(7) 0.042(5) Uiso 1 1 d . . .
N3C N 0.3695(5) -0.5327(14) 0.1185(7) 0.047(5) Uani 1 1 d . . .
N4A N 0.1411(4) -0.7797(11) -0.3034(6) 0.018(3) Uiso 1 1 d . . .
N4B N 0.1414(4) -0.2151(12) 0.0486(6) 0.030(4) Uani 1 1 d . . .
N4C N 0.3825(4) -0.3722(11) 0.4738(6) 0.025(4) Uani 1 1 d . . .
O1E O 0.1364(3) -0.3785(9) 0.1159(5) 0.025(3) Uani 1 1 d . . .
O1F O 0.4219(3) -0.5114(10) 0.4434(5) 0.033(3) Uani 1 1 d . . .
O1W O 0.3269(3) -0.2582(9) 0.3469(5) 0.024(3) Uani 1 1 d . . .
O2E O 0.1536(3) -0.5502(8) 0.1361(4) 0.014(3) Uani 1 1 d . . .
O2F O 0.4249(3) -0.6911(9) 0.4496(5) 0.024(3) Uani 1 1 d . . .
O2W O 0.0464(3) -0.3927(10) 0.0293(5) 0.039(4) Uani 1 1 d . . .
O3E O 0.3357(3) -0.5197(9) 0.3566(5) 0.023(3) Uani 1 1 d . . .
O3F O 0.5798(3) -0.7681(9) 0.5675(4) 0.022(3) Uani 1 1 d . . .
O4E O 0.2072(3) -0.1525(9) 0.1919(4) 0.019(3) Uani 1 1 d . . .
O4F O 0.5296(3) -0.8749(9) 0.5259(5) 0.027(3) Uani 1 1 d . . .
O4N O 0.2453(4) -0.9828(11) 0.1440(6) 0.052(4) Uani 1 1 d . . .
O5N O 0.2546(4) -0.9171(12) 0.0887(6) 0.051(4) Uani 1 1 d . . .
O6N O 0.2696(5) -1.0875(13) 0.1173(6) 0.055(4) Uani 1 1 d . . .
O1N O 0.4850(6) -0.788(2) 0.3796(10) 0.123(8) Uiso 1 1 d . . .
O2N O 0.4770(6) -0.623(2) 0.3775(9) 0.122(8) Uiso 1 1 d . . .
O3N O 0.4844(8) -0.693(3) 0.3272(13) 0.177(12) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cd1 N1C 2.269(13) . ?
Cd1 O1W 2.287(11) . ?
Cd1 N4C 2.311(15) . ?
Cd1 O1F 2.318(12) . ?
Cd1 O3F 2.321(12) 5_646 ?
Cd1 O3E 2.333(12) . ?
Cd2 O2W 2.241(13) . ?
Cd2 O4F 2.345(12) 8_435 ?
Cd2 N1A 2.348(14) . ?
Cd2 O2E 2.349(10) . ?
Cd2 N1B 2.370(14) . ?
Cd2 O3F 2.503(12) 8_435 ?
Cd2 O1E 2.583(12) . ?
Cd3 O2F 2.272(11) 4 ?
Cd3 O1E 2.286(12) . ?
Cd3 N4B 2.336(16) . ?
Cd3 O3E 2.349(11) 4 ?
Cd3 N4A 2.352(13) 6_546 ?
Cd3 O4E 2.433(11) . ?
Cd3 C5E 2.754(18) 4 ?
C1A N1A 1.36(2) . ?
C1A C2A 1.42(3) . ?
C1B N1B 1.36(2) . ?
C1B C2B 1.44(2) . ?
C1C N1C 1.37(2) . ?
C1C C2C 1.38(2) . ?
C1D C2D 1.37(3) . ?
C1D N1D 1.38(3) . ?
C1E O1E 1.259(19) . ?
C1E O2E 1.272(19) . ?
C1E C2E 1.52(2) . ?
C1F O1F 1.27(2) . ?
C1F O2F 1.29(2) . ?
C1F C2F 1.50(2) . ?
C2A C3A 1.42(3) . ?
C2B C3B 1.37(3) . ?
C2C C3C 1.41(2) . ?
C2D C3D 1.43(2) . ?
C2E C3E 1.54(2) . ?
C2F C3F 1.60(2) . ?
C3A C4A 1.42(2) . ?
C3A C6A 1.45(2) . ?
C3B C4B 1.37(3) . ?
C3B C6B 1.49(3) . ?
C3C C4C 1.40(2) . ?
C3C C6C 1.48(3) . ?
C3D C4D 1.39(3) . ?
C3D C6D 1.44(2) . ?
C3E C4E 1.52(2) . ?
C3F C4F 1.56(2) . ?
C4A C5A 1.43(2) . ?
C4B C5B 1.42(3) . ?
C4C C5C 1.36(2) . ?
C4D C5D 1.41(3) . ?
C4E C5E 1.50(2) . ?
C4F C5F 1.48(2) . ?
C5A N1A 1.34(2) . ?
C5B N1B 1.33(2) . ?
C5C N1C 1.41(2) . ?
C5D N1D 1.35(2) . ?
C5E O4E 1.26(2) 4_545 ?
C5E O3E 1.34(2) . ?
C5E Cd3 2.754(18) 4_545 ?
C5F O4F 1.29(2) . ?
C5F O3F 1.29(2) . ?
C6A N2A 1.27(2) . ?
C6B N2B 1.31(2) . ?
C6C N2C 1.27(2) . ?
C6D N2D 1.30(2) . ?
C7A N3A 1.34(2) . ?
C7A C10A 1.48(2) . ?
C7B N3B 1.27(2) . ?
C7B C10B 1.49(3) 6_546 ?
C7C N3C 1.28(2) . ?
C7C C10C 1.49(3) 6_545 ?
C8A N4A 1.34(2) . ?
C8A C9A 1.44(2) . ?
C8B N4B 1.33(2) . ?
C8B C9B 1.41(3) . ?
C8C N4C 1.36(2) . ?
C8C C9C 1.37(2) . ?
C9A C10A 1.36(2) . ?
C9B C10B 1.38(3) . ?
C9C C10C 1.40(3) . ?
C10A C11A 1.41(2) . ?
C10B C11B 1.40(2) . ?
C10B C7B 1.49(3) 6_545 ?
C10C C11C 1.39(2) . ?
C10C C7C 1.49(3) 6_546 ?
C11A C12A 1.39(2) . ?
C11B C12B 1.37(2) . ?
C11C C12C 1.31(2) . ?
C12A N4A 1.36(2) . ?
C12B N4B 1.39(2) . ?
C12C N4C 1.38(2) . ?
N1N O1N 1.13(3) . ?
N1N O3N 1.18(3) . ?
N1N O2N 1.22(3) . ?
N2A N3A 1.42(2) . ?
N2B N3B 1.43(2) . ?
N2C N3C 1.39(2) . ?
N2D N2D 1.42(3) 7_545 ?
N2N O5N 1.25(2) . ?
N2N O4N 1.29(2) . ?
N2N O6N 1.31(2) . ?
N4A Cd3 2.352(13) 6_545 ?
O2F Cd3 2.272(11) 4_545 ?
O3E Cd3 2.349(11) 4_545 ?
O3F Cd1 2.321(12) 5_646 ?
O3F Cd2 2.503(12) 8_536 ?
O4E C5E 1.26(2) 4 ?
O4F Cd2 2.345(12) 8_536 ?

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
N1C Cd1 O1W 93.2(4) . . ?
N1C Cd1 N4C 174.2(5) . . ?
O1W Cd1 N4C 92.1(4) . . ?
N1C Cd1 O1F 90.3(5) . . ?
O1W Cd1 O1F 170.3(4) . . ?
N4C Cd1 O1F 84.1(5) . . ?
N1C Cd1 O3F 91.7(4) . 5_646 ?
O1W Cd1 O3F 91.2(4) . 5_646 ?
N4C Cd1 O3F 90.5(4) . 5_646 ?
O1F Cd1 O3F 97.7(4) . 5_646 ?
N1C Cd1 O3E 86.1(4) . . ?
O1W Cd1 O3E 90.1(4) . . ?
N4C Cd1 O3E 91.5(4) . . ?
O1F Cd1 O3E 81.1(4) . . ?
O3F Cd1 O3E 177.5(4) 5_646 . ?
O2W Cd2 O4F 81.1(4) . 8_435 ?
O2W Cd2 N1A 96.1(5) . . ?
O4F Cd2 N1A 97.8(4) 8_435 . ?
O2W Cd2 O2E 134.8(4) . . ?
O4F Cd2 O2E 143.6(4) 8_435 . ?
N1A Cd2 O2E 86.0(4) . . ?
O2W Cd2 N1B 95.9(5) . . ?
O4F Cd2 N1B 85.0(4) 8_435 . ?
N1A Cd2 N1B 168.0(5) . . ?
O2E Cd2 N1B 84.9(4) . . ?
O2W Cd2 O3F 135.0(4) . 8_435 ?
O4F Cd2 O3F 54.3(4) 8_435 8_435 ?
N1A Cd2 O3F 85.8(4) . 8_435 ?
O2E Cd2 O3F 90.2(4) . 8_435 ?
N1B Cd2 O3F 86.4(4) . 8_435 ?
O2W Cd2 O1E 81.5(4) . . ?
O4F Cd2 O1E 161.3(4) 8_435 . ?
N1A Cd2 O1E 90.7(4) . . ?
O2E Cd2 O1E 53.3(4) . . ?
N1B Cd2 O1E 90.2(4) . . ?
O3F Cd2 O1E 143.5(4) 8_435 . ?
O2F Cd3 O1E 88.3(4) 4 . ?
O2F Cd3 N4B 86.1(5) 4 . ?
O1E Cd3 N4B 82.6(5) . . ?
O2F Cd3 O3E 110.1(4) 4 4 ?
O1E Cd3 O3E 161.0(4) . 4 ?
N4B Cd3 O3E 93.9(5) . 4 ?
O2F Cd3 N4A 97.1(4) 4 6_546 ?
O1E Cd3 N4A 83.8(4) . 6_546 ?
N4B Cd3 N4A 165.9(5) . 6_546 ?
O3E Cd3 N4A 97.8(4) 4 6_546 ?
O2F Cd3 O4E 166.0(4) 4 . ?
O1E Cd3 O4E 105.5(4) . . ?
N4B Cd3 O4E 93.4(4) . . ?
O3E Cd3 O4E 55.9(4) 4 . ?
N4A Cd3 O4E 86.8(4) 6_546 . ?
O2F Cd3 C5E 139.0(5) 4 4 ?
O1E Cd3 C5E 132.7(5) . 4 ?
N4B Cd3 C5E 97.0(5) . 4 ?
O3E Cd3 C5E 29.0(5) 4 4 ?
N4A Cd3 C5E 89.6(5) 6_546 4 ?
O4E Cd3 C5E 27.2(4) . 4 ?
N1A C1A C2A 121.9(17) . . ?
N1B C1B C2B 122.9(16) . . ?
N1C C1C C2C 123.2(18) . . ?
C2D C1D N1D 122(2) . . ?
O1E C1E O2E 122.8(15) . . ?
O1E C1E C2E 120.4(16) . . ?
O2E C1E C2E 116.8(15) . . ?
O1F C1F O2F 122.4(16) . . ?
O1F C1F C2F 117.2(17) . . ?
O2F C1F C2F 120.4(16) . . ?
C3A C2A C1A 120.1(17) . . ?
C3B C2B C1B 117.6(18) . . ?
C1C C2C C3C 120.7(18) . . ?
C1D C2D C3D 120.9(19) . . ?
C1E C2E C3E 117.0(16) . . ?
C1F C2F C3F 114.5(16) . . ?
C4A C3A C2A 118.3(17) . . ?
C4A C3A C6A 122.4(16) . . ?
C2A C3A C6A 119.2(17) . . ?
C4B C3B C2B 119.8(19) . . ?
C4B C3B C6B 117.3(19) . . ?
C2B C3B C6B 123.0(18) . . ?
C4C C3C C2C 117.7(16) . . ?
C4C C3C C6C 121.3(17) . . ?
C2C C3C C6C 120.9(17) . . ?
C4D C3D C2D 115.3(17) . . ?
C4D C3D C6D 120.2(17) . . ?
C2D C3D C6D 124.4(17) . . ?
C4E C3E C2E 112.7(14) . . ?
C4F C3F C2F 110.7(15) . . ?
C3A C4A C5A 116.2(16) . . ?
C3B C4B C5B 119.3(19) . . ?
C5C C4C C3C 118.2(17) . . ?
C3D C4D C5D 121.9(19) . . ?
C5E C4E C3E 114.9(15) . . ?
C5F C4F C3F 113.5(14) . . ?
N1A C5A C4A 126.2(16) . . ?
N1B C5B C4B 123.3(18) . . ?
C4C C5C N1C 126.3(17) . . ?
N1D C5D C4D 121.1(19) . . ?
O4E C5E O3E 119.6(15) 4_545 . ?
O4E C5E C4E 123.4(16) 4_545 . ?
O3E C5E C4E 116.8(16) . . ?
O4E C5E Cd3 62.0(9) 4_545 4_545 ?
O3E C5E Cd3 58.4(8) . 4_545 ?
C4E C5E Cd3 165.6(12) . 4_545 ?
O4F C5F O3F 118.7(17) . . ?
O4F C5F C4F 119.5(18) . . ?
O3F C5F C4F 121.8(18) . . ?
N2A C6A C3A 121.2(17) . . ?
N2B C6B C3B 116.6(18) . . ?
N2C C6C C3C 121.4(19) . . ?
N2D C6D C3D 119.6(18) . . ?
N3A C7A C10A 119.0(16) . . ?
N3B C7B C10B 121.1(17) . 6_546 ?
N3C C7C C10C 122(2) . 6_545 ?
N4A C8A C9A 123.5(16) . . ?
N4B C8B C9B 122.4(18) . . ?
N4C C8C C9C 122.3(17) . . ?
C10A C9A C8A 118.6(17) . . ?
C10B C9B C8B 120.9(18) . . ?
C8C C9C C10C 120.5(18) . . ?
C9A C10A C11A 117.8(16) . . ?
C9A C10A C7A 117.1(16) . . ?
C11A C10A C7A 125.1(16) . . ?
C9B C10B C11B 118.4(17) . . ?
C9B C10B C7B 121.3(18) . 6_545 ?
C11B C10B C7B 120.2(17) . 6_545 ?
C11C C10C C9C 115.8(17) . . ?
C11C C10C C7C 123.3(17) . 6_546 ?
C9C C10C C7C 120.8(17) . 6_546 ?
C12A C11A C10A 121.0(16) . . ?
C12B C11B C10B 117.0(16) . . ?
C12C C11C C10C 121.6(18) . . ?
N4A C12A C11A 121.5(16) . . ?
C11B C12B N4B 126.2(16) . . ?
C11C C12C N4C 124.5(18) . . ?
C5A N1A C1A 117.2(15) . . ?
C5A N1A Cd2 123.5(11) . . ?
C1A N1A Cd2 119.0(12) . . ?
C5B N1B C1B 116.9(15) . . ?
C5B N1B Cd2 120.4(12) . . ?
C1B N1B Cd2 122.2(11) . . ?
C1C N1C C5C 113.7(15) . . ?
C1C N1C Cd1 120.1(11) . . ?
C5C N1C Cd1 125.5(11) . . ?
C5D N1D C1D 118.2(17) . . ?
O1N N1N O3N 121(4) . . ?
O1N N1N O2N 124(3) . . ?
O3N N1N O2N 115(3) . . ?
C6A N2A N3A 112.9(15) . . ?
C6B N2B N3B 111.6(16) . . ?
C6C N2C N3C 112.7(16) . . ?
C6D N2D N2D 111.8(19) . 7_545 ?
O5N N2N O4N 121(2) . . ?
O5N N2N O6N 121.1(18) . . ?
O4N N2N O6N 118.0(17) . . ?
C7A N3A N2A 113.3(14) . . ?
C7B N3B N2B 114.0(17) . . ?
C7C N3C N2C 112.3(17) . . ?
C8A N4A C12A 117.5(15) . . ?
C8A N4A Cd3 122.7(11) . 6_545 ?
C12A N4A Cd3 119.2(11) . 6_545 ?
C8B N4B C12B 115.1(16) . . ?
C8B N4B Cd3 118.4(12) . . ?
C12B N4B Cd3 126.2(11) . . ?
C8C N4C C12C 115.2(15) . . ?
C8C N4C Cd1 121.4(11) . . ?
C12C N4C Cd1 122.5(12) . . ?
C1E O1E Cd3 132.4(11) . . ?
C1E O1E Cd2 86.7(10) . . ?
Cd3 O1E Cd2 140.4(5) . . ?
C1F O1F Cd1 160.3(11) . . ?
C1E O2E Cd2 97.2(9) . . ?
C1F O2F Cd3 113.8(10) . 4_545 ?
C5E O3E Cd1 145.4(11) . . ?
C5E O3E Cd3 92.6(10) . 4_545 ?
Cd1 O3E Cd3 119.4(5) . 4_545 ?
C5F O3F Cd1 136.5(12) . 5_646 ?
C5F O3F Cd2 89.8(11) . 8_536 ?
Cd1 O3F Cd2 133.7(5) 5_646 8_536 ?
C5E O4E Cd3 90.7(10) 4 . ?
C5F O4F Cd2 97.2(11) . 8_536 ?

_diffrn_measured_fraction_theta_max 0.970
_diffrn_reflns_theta_full        20.55
_diffrn_measured_fraction_theta_full 0.970
_refine_diff_density_max         6.241
_refine_diff_density_min         -1.410
_refine_diff_density_rms         0.214

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 0.789 0.250 341 71 ' '
2 1.000 0.289 0.250 341 71 ' '
3 0.261 0.755 0.181 19 10 ' '
4 0.761 0.255 0.181 19 10 ' '
5 0.239 0.255 0.319 19 9 ' '
6 0.739 0.755 0.319 19 9 ' '
7 0.500 0.211 0.750 341 71 ' '
8 1.000 0.711 0.750 341 71 ' '
9 0.261 0.245 0.681 19 10 ' '
10 0.761 0.745 0.681 19 10 ' '
11 0.239 0.745 0.819 19 9 ' '
12 0.739 0.245 0.819 19 9 ' '
_platon_squeeze_details          
;
;

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_ac2101_0m
_database_code_depnum_ccdc_archive 'CCDC 1032669'
_audit_update_record             
;
2014-11-02 deposited with the CCDC.
2015-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H20 Cd N4 O4'
_chemical_formula_weight         480.79

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'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/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                   10.8281(3)
_cell_length_b                   11.4808(4)
_cell_length_c                   15.8705(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.3510(10)
_cell_angle_gamma                90.00
_cell_volume                     1861.49(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    12591
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      30.51

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.716
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             968
_exptl_absorpt_coefficient_mu    1.208
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.672
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   'Bruker SADABS (Bruker, 1999)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'Phi and Omega Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25826
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_sigmaI/netI    0.0386
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.67
_diffrn_reflns_theta_max         30.56
_reflns_number_total             5697
_reflns_number_gt                4814
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker ApexII'
_computing_cell_refinement       'Bruker Apex II'
_computing_data_reduction        'Bruker Apex II'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0248P)²+0.6812P] 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         5697
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0263
_refine_ls_wR_factor_ref         0.0597
_refine_ls_wR_factor_gt          0.0566
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cd1 Cd -0.002765(11) 0.159198(11) 0.460895(7) 0.01077(4) Uani 1 1 d . . .
C1A C 0.25838(18) 0.17952(16) 0.64120(11) 0.0165(4) Uani 1 1 d . . .
H1A H 0.3051 0.1747 0.6016 0.020 Uiso 1 1 calc R . .
C1B C -0.19409(16) -0.01430(15) 0.55678(10) 0.0125(3) Uani 1 1 d . . .
C2A C 0.32617(18) 0.17513(16) 0.73189(12) 0.0170(4) Uani 1 1 d . . .
H2A H 0.4168 0.1675 0.7527 0.020 Uiso 1 1 calc R . .
C2B C -0.30357(17) 0.06243(17) 0.56415(11) 0.0177(4) Uani 1 1 d . . .
H2B1 H -0.3774 0.0559 0.5093 0.021 Uiso 1 1 calc R . .
H2B2 H -0.2742 0.1428 0.5697 0.021 Uiso 1 1 calc R . .
C3A C 0.25666(18) 0.18231(15) 0.79181(11) 0.0138(3) Uani 1 1 d . . .
C3B C -0.35015(17) 0.03348(18) 0.64278(12) 0.0195(4) Uani 1 1 d . . .
H3B1 H -0.4228 0.0841 0.6408 0.023 Uiso 1 1 calc R . .
H3B2 H -0.3817 -0.0462 0.6368 0.023 Uiso 1 1 calc R . .
C4A C 0.12163(17) 0.19520(17) 0.75748(11) 0.0155(3) Uani 1 1 d . . .
H4A H 0.0724 0.2012 0.7955 0.019 Uiso 1 1 calc R . .
C4B C -0.24224(17) 0.04757(17) 0.73304(11) 0.0177(4) Uani 1 1 d . . .
H4B1 H -0.1685 -0.0008 0.7338 0.021 Uiso 1 1 calc R . .
H4B2 H -0.2129 0.1279 0.7395 0.021 Uiso 1 1 calc R . .
C5A C 0.06144(18) 0.19900(17) 0.66557(11) 0.0155(3) Uani 1 1 d . . .
H5A H -0.0290 0.2078 0.6429 0.019 Uiso 1 1 calc R . .
C5B C -0.28430(18) 0.01524(17) 0.81280(11) 0.0184(4) Uani 1 1 d . . .
H5B1 H -0.3305 -0.0585 0.8007 0.022 Uiso 1 1 calc R . .
H5B2 H -0.3448 0.0738 0.8198 0.022 Uiso 1 1 calc R . .
C6A C 0.32027(18) 0.17493(15) 0.88916(11) 0.0150(3) Uani 1 1 d . . .
H6A H 0.2700 0.1755 0.9267 0.018 Uiso 1 1 calc R . .
C6B C -0.16891(18) 0.00503(16) 0.90104(11) 0.0179(4) Uani 1 1 d . . .
H6B1 H -0.2008 -0.0236 0.9475 0.021 Uiso 1 1 calc R . .
H6B2 H -0.1061 -0.0508 0.8937 0.021 Uiso 1 1 calc R . .
C7A C 0.61038(18) 0.13262(16) 1.04456(11) 0.0158(3) Uani 1 1 d . . .
H7A H 0.6525 0.1178 1.0032 0.019 Uiso 1 1 calc R . .
C7B C -0.10175(17) 0.12132(16) 0.92926(10) 0.0139(3) Uani 1 1 d . . .
C8A C -0.28359(18) 0.14122(16) 0.29613(11) 0.0161(4) Uani 1 1 d . . .
H8A H -0.3185 0.1560 0.3413 0.019 Uiso 1 1 calc R . .
C9A C -0.36640(17) 0.14388(16) 0.20841(12) 0.0163(3) Uani 1 1 d . . .
H9A H -0.4552 0.1592 0.1953 0.020 Uiso 1 1 calc R . .
C10A C -0.31486(17) 0.12331(16) 0.13991(11) 0.0131(3) Uani 1 1 d . . .
C11A C -0.18226(17) 0.09648(17) 0.16404(11) 0.0164(3) Uani 1 1 d . . .
H11A H -0.1447 0.0799 0.1205 0.020 Uiso 1 1 calc R . .
C12A C -0.10703(17) 0.09479(16) 0.25350(11) 0.0160(3) Uani 1 1 d . . .
H12A H -0.0187 0.0764 0.2686 0.019 Uiso 1 1 calc R . .
N1A N 0.12761(14) 0.19053(13) 0.60809(9) 0.0132(3) Uani 1 1 d . . .
N2A N 0.44465(16) 0.16773(15) 0.92194(10) 0.0197(3) Uani 1 1 d . . .
N3A N 0.48928(15) 0.16036(15) 1.01620(10) 0.0190(3) Uani 1 1 d . . .
N4A N -0.15439(14) 0.11817(14) 0.31910(9) 0.0139(3) Uani 1 1 d . . .
O1B O -0.11459(13) 0.02617(12) 0.52148(8) 0.0200(3) Uani 1 1 d . . .
O2B O -0.18372(13) -0.11732(12) 0.58453(8) 0.0176(3) Uani 1 1 d . . .
O3B O -0.00074(13) 0.14555(11) 0.90998(8) 0.0171(3) Uani 1 1 d . . .
O4B O -0.15192(12) 0.19316(11) 0.96917(8) 0.0163(2) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cd1 N1A 2.3225(14) . ?
Cd1 O1B 2.3441(13) . ?
Cd1 N4A 2.3523(14) . ?
Cd1 O4B 2.3747(13) 4_565 ?
Cd1 O3B 2.3854(13) 4_565 ?
Cd1 O2B 2.4069(12) 3_556 ?
Cd1 O1B 2.4467(14) 3_556 ?
Cd1 C7B 2.7191(18) 4_565 ?
C1A N1A 1.343(2) . ?
C1A C2A 1.383(2) . ?
C1B O2B 1.254(2) . ?
C1B O1B 1.261(2) . ?
C1B C2B 1.512(2) . ?
C2A C3A 1.397(2) . ?
C2B C3B 1.529(2) . ?
C3A C4A 1.389(3) . ?
C3A C6A 1.471(2) . ?
C3B C4B 1.528(2) . ?
C4A C5A 1.387(2) . ?
C4B C5B 1.526(2) . ?
C5A N1A 1.337(2) . ?
C5B C6B 1.542(3) . ?
C6A N2A 1.276(2) . ?
C6B C7B 1.515(3) . ?
C7A N3A 1.278(2) . ?
C7A C10A 1.465(2) 1_656 ?
C7B O3B 1.261(2) . ?
C7B O4B 1.267(2) . ?
C7B Cd1 2.7191(18) 4_566 ?
C8A N4A 1.350(2) . ?
C8A C9A 1.384(2) . ?
C9A C10A 1.397(2) . ?
C10A C11A 1.392(2) . ?
C10A C7A 1.465(2) 1_454 ?
C11A C12A 1.383(2) . ?
C12A N4A 1.331(2) . ?
N2A N3A 1.414(2) . ?
O1B Cd1 2.4467(14) 3_556 ?
O2B Cd1 2.4069(12) 3_556 ?
O3B Cd1 2.3854(13) 4_566 ?
O4B Cd1 2.3747(13) 4_566 ?

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
N1A Cd1 O1B 85.00(5) . . ?
N1A Cd1 N4A 172.86(5) . . ?
O1B Cd1 N4A 88.30(5) . . ?
N1A Cd1 O4B 91.82(5) . 4_565 ?
O1B Cd1 O4B 89.38(4) . 4_565 ?
N4A Cd1 O4B 85.64(5) . 4_565 ?
N1A Cd1 O3B 97.15(5) . 4_565 ?
O1B Cd1 O3B 144.61(4) . 4_565 ?
N4A Cd1 O3B 86.90(5) . 4_565 ?
O4B Cd1 O3B 55.30(4) 4_565 4_565 ?
N1A Cd1 O2B 92.38(5) . 3_556 ?
O1B Cd1 O2B 126.25(5) . 3_556 ?
N4A Cd1 O2B 93.57(5) . 3_556 ?
O4B Cd1 O2B 144.35(4) 4_565 3_556 ?
O3B Cd1 O2B 89.05(4) 4_565 3_556 ?
N1A Cd1 O1B 84.27(5) . 3_556 ?
O1B Cd1 O1B 72.88(5) . 3_556 ?
N4A Cd1 O1B 96.12(5) . 3_556 ?
O4B Cd1 O1B 162.08(4) 4_565 3_556 ?
O3B Cd1 O1B 142.50(4) 4_565 3_556 ?
O2B Cd1 O1B 53.49(4) 3_556 3_556 ?
N1A Cd1 C7B 96.50(5) . 4_565 ?
O1B Cd1 C7B 117.00(5) . 4_565 ?
N4A Cd1 C7B 84.34(5) . 4_565 ?
O4B Cd1 C7B 27.76(5) 4_565 4_565 ?
O3B Cd1 C7B 27.61(5) 4_565 4_565 ?
O2B Cd1 C7B 116.63(5) 3_556 4_565 ?
O1B Cd1 C7B 170.12(5) 3_556 4_565 ?
N1A C1A C2A 122.53(16) . . ?
O2B C1B O1B 120.57(16) . . ?
O2B C1B C2B 120.23(15) . . ?
O1B C1B C2B 119.20(16) . . ?
C1A C2A C3A 119.10(17) . . ?
C1B C2B C3B 114.55(15) . . ?
C4A C3A C2A 118.29(15) . . ?
C4A C3A C6A 118.94(16) . . ?
C2A C3A C6A 122.76(16) . . ?
C4B C3B C2B 112.67(15) . . ?
C5A C4A C3A 118.85(16) . . ?
C5B C4B C3B 113.96(15) . . ?
N1A C5A C4A 122.94(16) . . ?
C4B C5B C6B 113.40(15) . . ?
N2A C6A C3A 119.72(16) . . ?
C7B C6B C5B 111.51(15) . . ?
N3A C7A C10A 122.24(16) . 1_656 ?
O3B C7B O4B 121.88(17) . . ?
O3B C7B C6B 119.52(16) . . ?
O4B C7B C6B 118.56(16) . . ?
O3B C7B Cd1 61.30(9) . 4_566 ?
O4B C7B Cd1 60.82(9) . 4_566 ?
C6B C7B Cd1 172.88(12) . 4_566 ?
N4A C8A C9A 122.96(16) . . ?
C8A C9A C10A 119.10(16) . . ?
C11A C10A C9A 117.70(15) . . ?
C11A C10A C7A 117.83(15) . 1_454 ?
C9A C10A C7A 124.42(16) . 1_454 ?
C12A C11A C10A 119.23(16) . . ?
N4A C12A C11A 123.46(16) . . ?
C5A N1A C1A 118.27(15) . . ?
C5A N1A Cd1 114.39(11) . . ?
C1A N1A Cd1 126.13(11) . . ?
C6A N2A N3A 112.33(15) . . ?
C7A N3A N2A 109.79(14) . . ?
C12A N4A C8A 117.49(15) . . ?
C12A N4A Cd1 117.45(11) . . ?
C8A N4A Cd1 123.47(11) . . ?
C1B O1B Cd1 160.67(12) . . ?
C1B O1B Cd1 91.94(11) . 3_556 ?
Cd1 O1B Cd1 107.12(5) . 3_556 ?
C1B O2B Cd1 93.99(10) . 3_556 ?
C7B O3B Cd1 91.09(11) . 4_566 ?
C7B O4B Cd1 91.42(11) . 4_566 ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        30.56
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.818
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.102
####################################################################### 
# 
# 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_ac2100m_0m
_database_code_depnum_ccdc_archive 'CCDC 1032670'
_audit_update_record             
;
2014-11-02 deposited with the CCDC.
2015-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14 Cd N4 O4'
_chemical_formula_weight         438.71

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'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/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                   10.667(6)
_cell_length_b                   11.908(6)
_cell_length_c                   13.161(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.602(6)
_cell_angle_gamma                90.00
_cell_volume                     1574.8(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2149
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      24.87

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.850
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_absorpt_coefficient_mu    1.418
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.683
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   'Bruker SADABS (Bruker, 1999)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Axs APEX automatic diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8157
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_sigmaI/netI    0.0519
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2762
_reflns_number_gt                2353
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0380P)²+1.7484P] 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         2762
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.0901
_refine_ls_wR_factor_gt          0.0849
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cd1 Cd 0.06709(3) 0.05871(3) 0.39444(2) 0.01471(13) Uani 1 1 d . . .
C1A C -0.1940(5) 0.2089(4) 0.3685(4) 0.0228(11) Uani 1 1 d . . .
H1A H -0.2332 0.1382 0.3590 0.027 Uiso 1 1 calc R . .
C1B C -0.1656(4) -0.0847(4) 0.3216(3) 0.0140(10) Uani 1 1 d . . .
C2A C -0.2745(5) 0.3021(4) 0.3618(4) 0.0230(11) Uani 1 1 d . . .
H2A H -0.3651 0.2939 0.3494 0.028 Uiso 1 1 calc R . .
C2B C -0.2764(4) -0.1675(4) 0.3110(4) 0.0200(10) Uani 1 1 d . . .
H2B1 H -0.3501 -0.1277 0.3220 0.024 Uiso 1 1 calc R . .
H2B2 H -0.2451 -0.2226 0.3682 0.024 Uiso 1 1 calc R . .
C3A C -0.2166(5) 0.4082(4) 0.3740(4) 0.0237(11) Uani 1 1 d . . .
C3B C -0.3286(4) -0.2299(4) 0.2032(4) 0.0204(10) Uani 1 1 d . . .
H3B1 H -0.4050 -0.2742 0.2029 0.024 Uiso 1 1 calc R . .
H3B2 H -0.3597 -0.1745 0.1462 0.024 Uiso 1 1 calc R . .
C4A C -0.0804(5) 0.4163(4) 0.3888(4) 0.0266(12) Uani 1 1 d . . .
H4A H -0.0391 0.4859 0.3936 0.032 Uiso 1 1 calc R . .
C4B C -0.2304(4) -0.3074(4) 0.1759(4) 0.0157(10) Uani 1 1 d . . .
C5A C -0.0099(5) 0.3186(4) 0.3960(4) 0.0261(11) Uani 1 1 d . . .
H5A H 0.0808 0.3240 0.4073 0.031 Uiso 1 1 calc R . .
C6A C -0.2921(5) 0.5109(4) 0.3784(4) 0.0268(12) Uani 1 1 d . . .
H6A H -0.2520 0.5809 0.3831 0.032 Uiso 1 1 calc R . .
C7A C -0.5803(5) 0.6043(4) 0.3920(4) 0.0234(11) Uani 1 1 d . . .
H7A H -0.6186 0.5340 0.3912 0.028 Uiso 1 1 calc R . .
C8A C -0.6714(4) 0.9027(4) 0.4298(4) 0.0200(10) Uani 1 1 d . . .
H8A H -0.6298 0.9715 0.4514 0.024 Uiso 1 1 calc R . .
C9A C -0.5929(5) 0.8110(4) 0.4307(4) 0.0216(11) Uani 1 1 d . . .
H9A H -0.5009 0.8182 0.4510 0.026 Uiso 1 1 calc R . .
C10A C -0.6545(5) 0.7061(4) 0.4005(4) 0.0200(10) Uani 1 1 d . . .
C11A C -0.7917(5) 0.6991(4) 0.3745(4) 0.0229(11) Uani 1 1 d . . .
H11A H -0.8351 0.6304 0.3574 0.028 Uiso 1 1 calc R . .
C12A C -0.8626(5) 0.7969(4) 0.3745(4) 0.0218(11) Uani 1 1 d . . .
H12A H -0.9545 0.7919 0.3565 0.026 Uiso 1 1 calc R . .
N1A N -0.0635(4) 0.2157(3) 0.3879(3) 0.0161(8) Uani 1 1 d . . .
N2A N -0.4126(4) 0.5037(4) 0.3758(3) 0.0286(10) Uani 1 1 d . . .
N3A N -0.4627(4) 0.6118(4) 0.3857(3) 0.0289(10) Uani 1 1 d . . .
N4A N -0.8053(4) 0.8988(3) 0.3992(3) 0.0158(8) Uani 1 1 d . . .
O1B O -0.1014(3) -0.0498(2) 0.4172(2) 0.0168(7) Uani 1 1 d . . .
O2B O -0.1375(3) -0.0513(2) 0.2420(2) 0.0191(7) Uani 1 1 d . . .
O3B O -0.1299(3) -0.3440(3) 0.2491(2) 0.0200(7) Uani 1 1 d . . .
O4B O -0.2568(3) -0.3336(3) 0.0778(2) 0.0187(7) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cd1 O1B 2.313(3) . ?
Cd1 N1A 2.315(4) . ?
Cd1 O4B 2.318(3) 2 ?
Cd1 N4A 2.330(4) 1_645 ?
Cd1 O1B 2.384(3) 3_556 ?
Cd1 O3B 2.492(3) 2 ?
Cd1 C4B 2.741(5) 2 ?
C1A N1A 1.331(6) . ?
C1A C2A 1.388(7) . ?
C1B O2B 1.248(5) . ?
C1B O1B 1.283(5) . ?
C1B C2B 1.509(6) . ?
C2A C3A 1.392(7) . ?
C2B C3B 1.530(6) . ?
C3A C4A 1.403(7) . ?
C3A C6A 1.476(7) . ?
C3B C4B 1.528(6) . ?
C4A C5A 1.372(7) . ?
C4B O3B 1.254(5) . ?
C4B O4B 1.265(5) . ?
C4B Cd1 2.741(4) 2_545 ?
C5A N1A 1.341(6) . ?
C6A N2A 1.276(6) . ?
C7A N3A 1.288(6) . ?
C7A C10A 1.473(6) . ?
C8A N4A 1.348(5) . ?
C8A C9A 1.373(6) . ?
C9A C10A 1.405(7) . ?
C10A C11A 1.389(6) . ?
C11A C12A 1.389(7) . ?
C12A N4A 1.348(6) . ?
N2A N3A 1.417(6) . ?
N4A Cd1 2.330(4) 1_465 ?
O1B Cd1 2.384(3) 3_556 ?
O3B Cd1 2.492(3) 2_545 ?
O4B Cd1 2.318(3) 2_545 ?

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
O1B Cd1 N1A 88.40(12) . . ?
O1B Cd1 O4B 164.46(10) . 2 ?
N1A Cd1 O4B 92.39(12) . 2 ?
O1B Cd1 N4A 90.71(12) . 1_645 ?
N1A Cd1 N4A 178.88(13) . 1_645 ?
O4B Cd1 N4A 88.65(12) 2 1_645 ?
O1B Cd1 O1B 72.28(11) . 3_556 ?
N1A Cd1 O1B 87.44(11) . 3_556 ?
O4B Cd1 O1B 92.24(10) 2 3_556 ?
N4A Cd1 O1B 92.92(11) 1_645 3_556 ?
O1B Cd1 O3B 140.90(10) . 2 ?
N1A Cd1 O3B 84.70(12) . 2 ?
O4B Cd1 O3B 54.55(10) 2 2 ?
N4A Cd1 O3B 95.58(12) 1_645 2 ?
O1B Cd1 O3B 145.34(10) 3_556 2 ?
O1B Cd1 C4B 167.93(12) . 2 ?
N1A Cd1 C4B 87.73(13) . 2 ?
O4B Cd1 C4B 27.36(11) 2 2 ?
N4A Cd1 C4B 93.02(13) 1_645 2 ?
O1B Cd1 C4B 118.93(12) 3_556 2 ?
O3B Cd1 C4B 27.21(11) 2 2 ?
N1A C1A C2A 123.3(4) . . ?
O2B C1B O1B 121.3(4) . . ?
O2B C1B C2B 122.2(4) . . ?
O1B C1B C2B 116.5(4) . . ?
C1A C2A C3A 118.5(4) . . ?
C1B C2B C3B 115.6(4) . . ?
C2A C3A C4A 118.5(4) . . ?
C2A C3A C6A 122.0(4) . . ?
C4A C3A C6A 119.4(4) . . ?
C4B C3B C2B 116.5(4) . . ?
C5A C4A C3A 118.0(5) . . ?
O3B C4B O4B 122.6(4) . . ?
O3B C4B C3B 120.4(4) . . ?
O4B C4B C3B 117.0(4) . . ?
O3B C4B Cd1 65.3(2) . 2_545 ?
O4B C4B Cd1 57.4(2) . 2_545 ?
C3B C4B Cd1 174.3(3) . 2_545 ?
N1A C5A C4A 124.1(5) . . ?
N2A C6A C3A 120.1(5) . . ?
N3A C7A C10A 120.5(4) . . ?
N4A C8A C9A 123.8(4) . . ?
C8A C9A C10A 118.6(4) . . ?
C11A C10A C9A 118.5(4) . . ?
C11A C10A C7A 118.7(4) . . ?
C9A C10A C7A 122.8(4) . . ?
C12A C11A C10A 118.6(4) . . ?
N4A C12A C11A 123.4(4) . . ?
C1A N1A C5A 117.5(4) . . ?
C1A N1A Cd1 122.4(3) . . ?
C5A N1A Cd1 120.0(3) . . ?
C6A N2A N3A 110.1(4) . . ?
C7A N3A N2A 110.4(4) . . ?
C8A N4A C12A 116.9(4) . . ?
C8A N4A Cd1 122.0(3) . 1_465 ?
C12A N4A Cd1 121.0(3) . 1_465 ?
C1B O1B Cd1 103.7(3) . . ?
C1B O1B Cd1 148.3(3) . 3_556 ?
Cd1 O1B Cd1 107.72(11) . 3_556 ?
C4B O3B Cd1 87.5(3) . 2_545 ?
C4B O4B Cd1 95.3(3) . 2_545 ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.926
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.119
####################################################################### 
# 
# 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_a2104m_0m
_database_code_depnum_ccdc_archive 'CCDC 1032671'
_audit_update_record             
;
2015-03-01 deposited with the CCDC.
2015-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H22 Cd N4 O5'
_chemical_formula_weight         498.81

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'
Cd Cd -0.8075 1.2024 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.63(2)
_cell_length_b                   10.32(2)
_cell_length_c                   13.12(3)
_cell_angle_alpha                94.84(2)
_cell_angle_beta                 107.40(2)
_cell_angle_gamma                110.62(2)
_cell_volume                     1020(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    266
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      19.65

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.623
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    1.108
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.505
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   'Bruker SADABS (Bruker, 1999)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Axs APEX automatic diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2382
_diffrn_reflns_av_R_equivalents  0.0647
_diffrn_reflns_av_sigmaI/netI    0.1132
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         20.78
_reflns_number_total             1842
_reflns_number_gt                1377
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0819P)²+0.4975P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1842
_refine_ls_number_parameters     258
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0945
_refine_ls_R_factor_gt           0.0673
_refine_ls_wR_factor_ref         0.1650
_refine_ls_wR_factor_gt          0.1490
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.034
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cd1 Cd 0.85169(14) 0.07107(11) 0.40126(9) 0.0231(4) Uani 1 1 d . . .
C1A C 1.0013(18) 0.3685(15) 0.5755(11) 0.021(4) Uani 1 1 d . . .
H1A H 1.0782 0.3969 0.5373 0.026 Uiso 1 1 calc R . .
C1B C 0.7835(19) -0.1954(15) 0.5615(12) 0.024(4) Uani 1 1 d . . .
C1E C 0.595(2) 0.202(2) 0.0083(15) 0.059(5) Uani 1 1 d . . .
H1E1 H 0.5238 0.2303 -0.0506 0.071 Uiso 1 1 calc R . .
H1E2 H 0.5164 0.1162 0.0210 0.071 Uiso 1 1 calc R . .
C2A C 1.003(2) 0.4679(16) 0.6506(12) 0.032(4) Uani 1 1 d . . .
H2A H 1.0771 0.5624 0.6606 0.039 Uiso 1 1 calc R . .
C2B C 0.5882(18) -0.2682(16) 0.5456(12) 0.028(4) Uani 1 1 d . . .
H2B1 H 0.5301 -0.2057 0.5205 0.033 Uiso 1 1 calc R . .
H2B2 H 0.5356 -0.3532 0.4887 0.033 Uiso 1 1 calc R . .
C2E C 0.729(2) 0.1666(18) -0.0300(14) 0.049(5) Uani 1 1 d . . .
H2E1 H 0.8087 0.2504 -0.0426 0.074 Uiso 1 1 d R . .
H2E2 H 0.6679 0.0956 -0.0965 0.074 Uiso 1 1 d R . .
H2E3 H 0.7950 0.1314 0.0252 0.074 Uiso 1 1 d R . .
C3A C 0.8961(18) 0.4307(15) 0.7123(11) 0.021(4) Uani 1 1 d . . .
C3B C 0.5528(18) -0.3081(15) 0.6467(13) 0.031(4) Uani 1 1 d . . .
H3B1 H 0.6276 -0.3557 0.6800 0.037 Uiso 1 1 calc R . .
H3B2 H 0.4307 -0.3739 0.6261 0.037 Uiso 1 1 calc R . .
C4A C 0.7892(18) 0.2856(15) 0.6937(12) 0.025(4) Uani 1 1 d . . .
H4A H 0.7177 0.2540 0.7348 0.030 Uiso 1 1 calc R . .
C4B C 0.588(2) -0.1760(16) 0.7324(13) 0.034(4) Uani 1 1 d . . .
H4B1 H 0.5948 -0.2015 0.8026 0.041 Uiso 1 1 calc R . .
H4B2 H 0.7005 -0.1009 0.7413 0.041 Uiso 1 1 calc R . .
C5A C 0.7915(17) 0.1900(16) 0.6132(11) 0.021(4) Uani 1 1 d . . .
H5A H 0.7191 0.0946 0.6009 0.026 Uiso 1 1 calc R . .
C5B C 0.441(2) -0.1248(16) 0.6941(12) 0.027(4) Uani 1 1 d . . .
C6A C 0.893(2) 0.5391(15) 0.7903(12) 0.029(4) Uani 1 1 d . . .
H6A H 0.9598 0.6341 0.7953 0.035 Uiso 1 1 calc R . .
C7A C 0.7713(18) -0.4089(15) 0.0021(13) 0.028(4) Uani 1 1 d . . .
H7A H 0.7260 -0.5038 0.0058 0.034 Uiso 1 1 calc R . .
C8A C 0.8815(17) -0.0605(15) 0.1813(12) 0.023(4) Uiso 1 1 d . . .
H8A H 0.9370 0.0357 0.1842 0.027 Uiso 1 1 calc R . .
C9A C 0.873(2) -0.1562(16) 0.0969(11) 0.028(4) Uani 1 1 d . . .
H9A H 0.9247 -0.1240 0.0463 0.034 Uiso 1 1 calc R . .
C10A C 0.7853(18) -0.3006(16) 0.0883(12) 0.028(4) Uani 1 1 d . . .
C11A C 0.7162(19) -0.3413(16) 0.1712(12) 0.031(4) Uani 1 1 d . . .
H11A H 0.6622 -0.4366 0.1716 0.038 Uiso 1 1 calc R . .
C12A C 0.7302(19) -0.2359(17) 0.2531(12) 0.027(4) Uani 1 1 d U . .
H12A H 0.6788 -0.2630 0.3050 0.032 Uiso 1 1 calc R . .
N1A N 0.8934(14) 0.2300(12) 0.5534(9) 0.021(3) Uani 1 1 d . . .
N2A N 0.8004(16) 0.5053(13) 0.8524(10) 0.029(3) Uani 1 1 d . . .
N3A N 0.8201(16) 0.6250(12) 0.9226(11) 0.030(3) Uani 1 1 d . . .
N4A N 0.8148(14) -0.0990(11) 0.2581(9) 0.022(3) Uani 1 1 d . . .
O1B O 0.8330(12) -0.1027(10) 0.5077(8) 0.029(3) Uani 1 1 d . . .
O1E O 0.6640(15) 0.3074(11) 0.1020(9) 0.045(3) Uani 1 1 d . . .
O2B O 0.8951(13) -0.2314(10) 0.6288(8) 0.030(2) Uani 1 1 d . . .
O3B O 0.4535(12) -0.0290(10) 0.6451(8) 0.026(2) Uani 1 1 d . . .
O4B O 0.3015(12) -0.1885(10) 0.7165(8) 0.029(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cd1 N4A 2.325(12) . ?
Cd1 N1A 2.326(12) . ?
Cd1 O1B 2.356(10) . ?
Cd1 O3B 2.385(10) 2_656 ?
Cd1 O2B 2.398(11) 2_756 ?
Cd1 O4B 2.414(9) 2_656 ?
Cd1 O1B 2.511(11) 2_756 ?
Cd1 C5B 2.733(15) 2_656 ?
C1A N1A 1.352(17) . ?
C1A C2A 1.354(19) . ?
C1A H1A 0.9300 . ?
C1B O1B 1.266(16) . ?
C1B O2B 1.282(16) . ?
C1B C2B 1.52(2) . ?
C1E O1E 1.39(2) . ?
C1E C2E 1.53(2) . ?
C1E H1E1 0.9700 . ?
C1E H1E2 0.9700 . ?
C2A C3A 1.380(19) . ?
C2A H2A 0.9300 . ?
C2B C3B 1.506(19) . ?
C2B H2B1 0.9700 . ?
C2B H2B2 0.9700 . ?
C2E H2E1 0.9600 . ?
C2E H2E2 0.9600 . ?
C2E H2E3 0.9600 . ?
C3A C4A 1.41(2) . ?
C3A C6A 1.462(19) . ?
C3B C4B 1.57(2) . ?
C3B H3B1 0.9700 . ?
C3B H3B2 0.9700 . ?
C4A C5A 1.392(19) . ?
C4A H4A 0.9300 . ?
C4B C5B 1.512(19) . ?
C4B H4B1 0.9700 . ?
C4B H4B2 0.9700 . ?
C5A N1A 1.331(16) . ?
C5A H5A 0.9300 . ?
C5B O3B 1.215(16) . ?
C5B O4B 1.287(17) . ?
C5B Cd1 2.733(15) 2_656 ?
C6A N2A 1.294(18) . ?
C6A H6A 0.9300 . ?
C7A N3A 1.269(17) 1_544 ?
C7A C10A 1.47(2) . ?
C7A H7A 0.9300 . ?
C8A N4A 1.326(17) . ?
C8A C9A 1.385(19) . ?
C8A H8A 0.9300 . ?
C9A C10A 1.39(2) . ?
C9A H9A 0.9300 . ?
C10A C11A 1.42(2) . ?
C11A C12A 1.41(2) . ?
C11A H11A 0.9300 . ?
C12A N4A 1.328(17) . ?
C12A H12A 0.9300 . ?
N2A N3A 1.404(16) . ?
N3A C7A 1.269(17) 1_566 ?
O1B Cd1 2.511(11) 2_756 ?
O2B Cd1 2.398(10) 2_756 ?
O3B Cd1 2.385(10) 2_656 ?
O4B Cd1 2.414(9) 2_656 ?

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
N4A Cd1 N1A 175.6(4) . . ?
N4A Cd1 O1B 87.5(4) . . ?
N1A Cd1 O1B 88.3(4) . . ?
N4A Cd1 O3B 96.5(4) . 2_656 ?
N1A Cd1 O3B 84.9(4) . 2_656 ?
O1B Cd1 O3B 93.1(3) . 2_656 ?
N4A Cd1 O2B 89.3(4) . 2_756 ?
N1A Cd1 O2B 92.5(4) . 2_756 ?
O1B Cd1 O2B 129.4(3) . 2_756 ?
O3B Cd1 O2B 137.4(3) 2_656 2_756 ?
N4A Cd1 O4B 94.2(4) . 2_656 ?
N1A Cd1 O4B 90.0(4) . 2_656 ?
O1B Cd1 O4B 147.3(3) . 2_656 ?
O3B Cd1 O4B 54.2(3) 2_656 2_656 ?
O2B Cd1 O4B 83.3(4) 2_756 2_656 ?
N4A Cd1 O1B 90.9(3) . 2_756 ?
N1A Cd1 O1B 86.9(4) . 2_756 ?
O1B Cd1 O1B 75.9(4) . 2_756 ?
O3B Cd1 O1B 166.5(3) 2_656 2_756 ?
O2B Cd1 O1B 53.7(3) 2_756 2_756 ?
O4B Cd1 O1B 136.6(3) 2_656 2_756 ?
N4A Cd1 C5B 98.6(4) . 2_656 ?
N1A Cd1 C5B 84.5(4) . 2_656 ?
O1B Cd1 C5B 119.4(4) . 2_656 ?
O3B Cd1 C5B 26.4(4) 2_656 2_656 ?
O2B Cd1 C5B 111.0(4) 2_756 2_656 ?
O4B Cd1 C5B 28.1(4) 2_656 2_656 ?
O1B Cd1 C5B 162.1(4) 2_756 2_656 ?
N1A C1A C2A 123.2(13) . . ?
N1A C1A H1A 118.4 . . ?
C2A C1A H1A 118.4 . . ?
O1B C1B O2B 121.1(13) . . ?
O1B C1B C2B 120.1(13) . . ?
O2B C1B C2B 118.8(14) . . ?
O1E C1E C2E 116.4(14) . . ?
O1E C1E H1E1 108.2 . . ?
C2E C1E H1E1 108.2 . . ?
O1E C1E H1E2 108.2 . . ?
C2E C1E H1E2 108.2 . . ?
H1E1 C1E H1E2 107.4 . . ?
C1A C2A C3A 120.7(14) . . ?
C1A C2A H2A 119.6 . . ?
C3A C2A H2A 119.6 . . ?
C3B C2B C1B 114.4(12) . . ?
C3B C2B H2B1 108.7 . . ?
C1B C2B H2B1 108.7 . . ?
C3B C2B H2B2 108.7 . . ?
C1B C2B H2B2 108.7 . . ?
H2B1 C2B H2B2 107.6 . . ?
C1E C2E H2E1 109.5 . . ?
C1E C2E H2E2 109.5 . . ?
H2E1 C2E H2E2 109.5 . . ?
C1E C2E H2E3 109.5 . . ?
H2E1 C2E H2E3 109.5 . . ?
H2E2 C2E H2E3 109.5 . . ?
C2A C3A C4A 116.5(13) . . ?
C2A C3A C6A 120.5(13) . . ?
C4A C3A C6A 122.9(13) . . ?
C2B C3B C4B 112.3(12) . . ?
C2B C3B H3B1 109.1 . . ?
C4B C3B H3B1 109.1 . . ?
C2B C3B H3B2 109.1 . . ?
C4B C3B H3B2 109.1 . . ?
H3B1 C3B H3B2 107.9 . . ?
C5A C4A C3A 119.4(13) . . ?
C5A C4A H4A 120.3 . . ?
C3A C4A H4A 120.3 . . ?
C5B C4B C3B 109.7(12) . . ?
C5B C4B H4B1 109.7 . . ?
C3B C4B H4B1 109.7 . . ?
C5B C4B H4B2 109.7 . . ?
C3B C4B H4B2 109.7 . . ?
H4B1 C4B H4B2 108.2 . . ?
N1A C5A C4A 122.4(14) . . ?
N1A C5A H5A 118.8 . . ?
C4A C5A H5A 118.8 . . ?
O3B C5B O4B 121.9(13) . . ?
O3B C5B C4B 122.0(13) . . ?
O4B C5B C4B 116.1(14) . . ?
O3B C5B Cd1 60.6(7) . 2_656 ?
O4B C5B Cd1 62.0(7) . 2_656 ?
C4B C5B Cd1 170.7(10) . 2_656 ?
N2A C6A C3A 121.2(13) . . ?
N2A C6A H6A 119.4 . . ?
C3A C6A H6A 119.4 . . ?
N3A C7A C10A 121.0(13) 1_544 . ?
N3A C7A H7A 119.5 1_544 . ?
C10A C7A H7A 119.5 . . ?
N4A C8A C9A 123.4(13) . . ?
N4A C8A H8A 118.3 . . ?
C9A C8A H8A 118.3 . . ?
C8A C9A C10A 119.6(14) . . ?
C8A C9A H9A 120.2 . . ?
C10A C9A H9A 120.2 . . ?
C9A C10A C11A 116.8(14) . . ?
C9A C10A C7A 123.1(14) . . ?
C11A C10A C7A 120.0(14) . . ?
C12A C11A C10A 119.3(14) . . ?
C12A C11A H11A 120.3 . . ?
C10A C11A H11A 120.3 . . ?
N4A C12A C11A 121.8(13) . . ?
N4A C12A H12A 119.1 . . ?
C11A C12A H12A 119.1 . . ?
C5A N1A C1A 117.5(11) . . ?
C5A N1A Cd1 119.7(9) . . ?
C1A N1A Cd1 122.1(9) . . ?
C6A N2A N3A 111.9(12) . . ?
C7A N3A N2A 111.1(11) 1_566 . ?
C8A N4A C12A 119.0(12) . . ?
C8A N4A Cd1 120.2(9) . . ?
C12A N4A Cd1 120.7(9) . . ?
C1B O1B Cd1 164.9(9) . . ?
C1B O1B Cd1 90.2(8) . 2_756 ?
Cd1 O1B Cd1 104.1(4) . 2_756 ?
C1B O2B Cd1 95.0(9) . 2_756 ?
C5B O3B Cd1 93.0(8) . 2_656 ?
C5B O4B Cd1 89.9(8) . 2_656 ?

_diffrn_measured_fraction_theta_max 0.863
_diffrn_reflns_theta_full        20.78
_diffrn_measured_fraction_theta_full 0.863
_refine_diff_density_max         0.834
_refine_diff_density_min         -0.943
_refine_diff_density_rms         0.145
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_acr2142_0m
_database_code_depnum_ccdc_archive 'CCDC 1032672'
_audit_update_record             
;
2015-03-01 deposited with the CCDC.
2015-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H22 Cd N4 O6'
_chemical_formula_weight         502.80

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'
Cd Cd -0.8075 1.2024 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   Cc

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

_cell_length_a                   16.991(8)
_cell_length_b                   15.726(7)
_cell_length_c                   9.212(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 120.505(7)
_cell_angle_gamma                90.00
_cell_volume                     2121(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3062
_cell_measurement_theta_min      3.64
_cell_measurement_theta_max      26.80

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1016
_exptl_absorpt_coefficient_mu    1.070
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.644
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   'Bruker SADABS (Bruker, 1999)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'Phi and Omega Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8740
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_av_sigmaI/netI    0.0690
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.56
_diffrn_reflns_theta_max         26.89
_reflns_number_total             4335
_reflns_number_gt                3362
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker ApexII'
_computing_cell_refinement       'Bruker Apex II'
_computing_data_reduction        'Bruker Apex II'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0512P)²+6.4241P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.45(6)
_refine_ls_number_reflns         4335
_refine_ls_number_parameters     181
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.1167
_refine_ls_wR_factor_gt          0.1041
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.068
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cd1 Cd 0.45935(15) 0.12502(2) 0.7700(2) 0.02238(13) Uani 1 1 d . . .
N1A N 0.3093(3) 0.1076(4) 0.5522(6) 0.019(2) Uiso 1 1 d G . .
C1A C 0.2898(3) 0.0570(4) 0.4142(7) 0.034(3) Uiso 1 1 d G . .
H1A H 0.3371 0.0331 0.4049 0.041 Uiso 1 1 calc R . .
C2A C 0.1996(4) 0.0422(4) 0.2900(6) 0.030(3) Uiso 1 1 d G . .
H2A H 0.1866 0.0084 0.1976 0.036 Uiso 1 1 calc R . .
C3A C 0.1289(3) 0.0780(5) 0.3038(9) 0.027(3) Uani 1 1 d G . .
C4A C 0.1484(4) 0.1285(5) 0.4419(11) 0.038(5) Uani 1 1 d G . .
H4A H 0.1010 0.1525 0.4511 0.046 Uiso 1 1 calc R . .
C5A C 0.2386(5) 0.1434(5) 0.5660(8) 0.021(3) Uiso 1 1 d G . .
H5A H 0.2516 0.1772 0.6584 0.026 Uiso 1 1 calc R . .
C1B C 0.5096(10) 0.1931(13) 0.5480(17) 0.055(4) Uani 1 1 d D . .
C2B C 0.5571(11) 0.2581(8) 0.4830(15) 0.087(5) Uani 1 1 d D . .
H2B1 H 0.5270 0.3130 0.4596 0.104 Uiso 1 1 calc R . .
H2B2 H 0.6208 0.2656 0.5683 0.104 Uiso 1 1 calc R . .
C3B C 0.5492(9) 0.2213(7) 0.3220(11) 0.064(4) Uani 1 1 d . . .
H3B H 0.5678 0.1614 0.3392 0.077 Uiso 1 1 calc R . .
C4B C 0.4482(8) 0.2294(6) 0.1793(12) 0.054(3) Uani 1 1 d D . .
H4B1 H 0.4293 0.2883 0.1710 0.065 Uiso 1 1 calc R . .
H4B2 H 0.4103 0.1956 0.2083 0.065 Uiso 1 1 calc R . .
C5B C 0.4316(11) 0.1991(13) 0.001(2) 0.076(6) Uani 1 1 d D . .
C6A C 0.0333(10) 0.0635(9) 0.1710(17) 0.037(4) Uiso 1 1 d . . .
H6A H -0.0118 0.0988 0.1670 0.044 Uiso 1 1 calc R . .
C7A C -0.1093(8) -0.0635(8) -0.1425(13) 0.021(3) Uiso 1 1 d . . .
H7A H -0.0655 -0.1036 -0.1275 0.025 Uiso 1 1 calc R . .
C8A C 0.6348(6) 0.0483(5) 1.0963(10) 0.028(2) Uiso 1 1 d . . .
H8A H 0.5871 0.0190 1.0958 0.033 Uiso 1 1 calc R . .
C9A C 0.7244(6) 0.0318(6) 1.2241(10) 0.029(2) Uiso 1 1 d . . .
H9A H 0.7357 -0.0092 1.3050 0.035 Uiso 1 1 calc R . .
C10A C -0.2043(6) -0.0760(7) -0.2694(12) 0.026(3) Uiso 1 1 d . . .
C11A C -0.2272(5) -0.1346(6) -0.3975(11) 0.018(3) Uiso 1 1 d . . .
H11A H -0.1824 -0.1657 -0.4036 0.022 Uiso 1 1 calc R . .
C12A C 0.6823(7) 0.1451(6) 0.9856(12) 0.027(4) Uiso 1 1 d . . .
H12A H 0.6681 0.1867 0.9043 0.032 Uiso 1 1 calc R . .
C31B C 0.6152(11) 0.2763(12) 0.2767(16) 0.114(7) Uani 1 1 d . . .
H31A H 0.5948 0.3347 0.2501 0.171 Uiso 1 1 d R . .
H31B H 0.6139 0.2508 0.1789 0.171 Uiso 1 1 d R . .
H31C H 0.6789 0.2766 0.3698 0.171 Uiso 1 1 d R . .
N2A N 0.0100(6) 0.0056(5) 0.0630(10) 0.029(2) Uiso 1 1 d . . .
N3A N -0.0862(6) 0.0045(5) -0.0504(10) 0.026(2) Uiso 1 1 d . . .
N4A N 0.6161(5) 0.1042(6) 0.9764(9) 0.031(3) Uiso 1 1 d . . .
O1B O 0.4985(8) 0.2382(8) 0.6572(13) 0.048(3) Uani 1 1 d D . .
O1W O 0.4653(10) -0.0213(3) 0.7670(18) 0.0358(15) Uani 1 1 d D . .
H11W H 0.4228 -0.0183 0.7854 0.043 Uiso 1 1 d RD . .
H12W H 0.4443 -0.0456 0.6704 0.043 Uiso 1 1 d RD . .
O2B O 0.4943(15) 0.1149(9) 0.537(2) 0.065(6) Uani 1 1 d D . .
O2W O 0.295(7) -0.276(5) 0.673(15) 1.01(10) Uani 1 1 d . . .
O3B O 0.4307(8) 0.2393(6) -0.1005(13) 0.049(3) Uani 1 1 d D . .
O4B O 0.4294(13) 0.1178(8) 0.0087(16) 0.050(5) Uani 1 1 d D . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cd1 O1W 2.303(4) . ?
Cd1 N1A 2.325(5) . ?
Cd1 O1B 2.322(11) . ?
Cd1 O3B 2.341(10) 1_556 ?
Cd1 N4A 2.383(8) . ?
Cd1 O2B 2.507(16) . ?
Cd1 O4B 2.498(13) 1_556 ?
Cd1 C5B 2.668(15) 1_556 ?
N1A C1A 1.3900 . ?
N1A C5A 1.3900 . ?
C1A C2A 1.3900 . ?
C1A H1A 0.9300 . ?
C2A C3A 1.3900 . ?
C2A H2A 0.9300 . ?
C3A C4A 1.3900 . ?
C3A C6A 1.473(16) . ?
C4A C5A 1.3900 . ?
C4A H4A 0.9300 . ?
C5A H5A 0.9300 . ?
C1B O2B 1.25(2) . ?
C1B O1B 1.320(19) . ?
C1B C2B 1.59(2) . ?
C2B C3B 1.533(14) . ?
C2B H2B1 0.9700 . ?
C2B H2B2 0.9700 . ?
C3B C4B 1.548(16) . ?
C3B C31B 1.630(15) . ?
C3B H3B 0.9800 . ?
C4B C5B 1.594(18) . ?
C4B H4B1 0.9700 . ?
C4B H4B2 0.9700 . ?
C5B O3B 1.12(2) . ?
C5B O4B 1.28(2) . ?
C5B Cd1 2.668(15) 1_554 ?
C6A N2A 1.256(16) . ?
C6A H6A 0.9300 . ?
C7A N3A 1.295(14) . ?
C7A C10A 1.448(15) . ?
C7A H7A 0.9300 . ?
C8A N4A 1.318(10) . ?
C8A C9A 1.396(10) . ?
C8A H8A 0.9300 . ?
C9A C10A 1.371(11) 2_656 ?
C9A H9A 0.9300 . ?
C10A C9A 1.371(11) 2_453 ?
C10A C11A 1.388(10) . ?
C11A C12A 1.367(10) 2_453 ?
C11A H11A 0.9300 . ?
C12A N4A 1.261(10) . ?
C12A C11A 1.367(10) 2_656 ?
C12A H12A 0.9300 . ?
C31B H31A 0.9681 . ?
C31B H31B 0.9760 . ?
C31B H31C 0.9818 . ?
N2A N3A 1.426(6) . ?
O1W H11W 0.8215 . ?
O1W H12W 0.8618 . ?
O3B Cd1 2.341(10) 1_554 ?
O4B Cd1 2.498(12) 1_554 ?

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
O1W Cd1 N1A 84.7(4) . . ?
O1W Cd1 O1B 137.3(5) . . ?
N1A Cd1 O1B 98.1(3) . . ?
O1W Cd1 O3B 142.6(4) . 1_556 ?
N1A Cd1 O3B 96.3(3) . 1_556 ?
O1B Cd1 O3B 79.7(2) . 1_556 ?
O1W Cd1 N4A 80.5(4) . . ?
N1A Cd1 N4A 164.65(18) . . ?
O1B Cd1 N4A 90.2(4) . . ?
O3B Cd1 N4A 97.8(4) 1_556 . ?
O1W Cd1 O2B 84.0(5) . . ?
N1A Cd1 O2B 83.4(5) . . ?
O1B Cd1 O2B 54.5(4) . . ?
O3B Cd1 O2B 133.3(4) 1_556 . ?
N4A Cd1 O2B 91.1(5) . . ?
O1W Cd1 O4B 89.7(5) . 1_556 ?
N1A Cd1 O4B 97.5(5) . 1_556 ?
O1B Cd1 O4B 131.4(4) . 1_556 ?
O3B Cd1 O4B 53.1(4) 1_556 1_556 ?
N4A Cd1 O4B 86.3(5) . 1_556 ?
O2B Cd1 O4B 173.5(3) . 1_556 ?
O1W Cd1 C5B 118.2(6) . 1_556 ?
N1A Cd1 C5B 100.3(4) . 1_556 ?
O1B Cd1 C5B 103.2(5) . 1_556 ?
O3B Cd1 C5B 24.8(5) 1_556 1_556 ?
N4A Cd1 C5B 90.1(5) . 1_556 ?
O2B Cd1 C5B 157.7(5) . 1_556 ?
O4B Cd1 C5B 28.5(5) 1_556 1_556 ?
C1A N1A C5A 120.0 . . ?
C1A N1A Cd1 120.3(3) . . ?
C5A N1A Cd1 119.6(3) . . ?
C2A C1A N1A 120.0 . . ?
C2A C1A H1A 120.0 . . ?
N1A C1A H1A 120.0 . . ?
C1A C2A C3A 120.0 . . ?
C1A C2A H2A 120.0 . . ?
C3A C2A H2A 120.0 . . ?
C4A C3A C2A 120.0 . . ?
C4A C3A C6A 119.9(8) . . ?
C2A C3A C6A 120.1(8) . . ?
C3A C4A C5A 120.0 . . ?
C3A C4A H4A 120.0 . . ?
C5A C4A H4A 120.0 . . ?
C4A C5A N1A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
N1A C5A H5A 120.0 . . ?
O2B C1B O1B 119.1(15) . . ?
O2B C1B C2B 136.3(15) . . ?
O1B C1B C2B 103.7(15) . . ?
C3B C2B C1B 108.0(9) . . ?
C3B C2B H2B1 110.1 . . ?
C1B C2B H2B1 110.1 . . ?
C3B C2B H2B2 110.1 . . ?
C1B C2B H2B2 110.1 . . ?
H2B1 C2B H2B2 108.4 . . ?
C2B C3B C4B 107.8(11) . . ?
C2B C3B C31B 108.3(7) . . ?
C4B C3B C31B 110.4(9) . . ?
C2B C3B H3B 110.1 . . ?
C4B C3B H3B 110.1 . . ?
C31B C3B H3B 110.1 . . ?
C3B C4B C5B 113.0(10) . . ?
C3B C4B H4B1 109.0 . . ?
C5B C4B H4B1 109.0 . . ?
C3B C4B H4B2 109.0 . . ?
C5B C4B H4B2 109.0 . . ?
H4B1 C4B H4B2 107.8 . . ?
O3B C5B O4B 128.4(15) . . ?
O3B C5B C4B 127.7(16) . . ?
O4B C5B C4B 103.5(15) . . ?
O3B C5B Cd1 61.0(9) . 1_554 ?
O4B C5B Cd1 68.4(8) . 1_554 ?
C4B C5B Cd1 160.5(11) . 1_554 ?
N2A C6A C3A 122.7(12) . . ?
N2A C6A H6A 118.7 . . ?
C3A C6A H6A 118.7 . . ?
N3A C7A C10A 118.9(11) . . ?
N3A C7A H7A 120.5 . . ?
C10A C7A H7A 120.5 . . ?
N4A C8A C9A 121.7(7) . . ?
N4A C8A H8A 119.1 . . ?
C9A C8A H8A 119.1 . . ?
C10A C9A C8A 120.3(7) 2_656 . ?
C10A C9A H9A 119.9 2_656 . ?
C8A C9A H9A 119.9 . . ?
C9A C10A C11A 116.0(7) 2_453 . ?
C9A C10A C7A 124.4(9) 2_453 . ?
C11A C10A C7A 119.5(9) . . ?
C12A C11A C10A 117.9(7) 2_453 . ?
C12A C11A H11A 121.1 2_453 . ?
C10A C11A H11A 121.1 . . ?
N4A C12A C11A 126.8(7) . 2_656 ?
N4A C12A H12A 116.6 . . ?
C11A C12A H12A 116.6 2_656 . ?
C3B C31B H31A 111.3 . . ?
C3B C31B H31B 108.7 . . ?
H31A C31B H31B 108.6 . . ?
C3B C31B H31C 112.1 . . ?
H31A C31B H31C 108.1 . . ?
H31B C31B H31C 107.9 . . ?
C6A N2A N3A 111.8(8) . . ?
C7A N3A N2A 110.1(7) . . ?
C12A N4A C8A 117.2(7) . . ?
C12A N4A Cd1 125.5(6) . . ?
C8A N4A Cd1 117.2(6) . . ?
C1B O1B Cd1 96.6(10) . . ?
Cd1 O1W H11W 83.9 . . ?
Cd1 O1W H12W 117.2 . . ?
H11W O1W H12W 106.9 . . ?
C1B O2B Cd1 89.8(10) . . ?
C5B O3B Cd1 94.2(10) . 1_554 ?
C5B O4B Cd1 83.1(9) . 1_554 ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         1.159
_refine_diff_density_min         -0.546
_refine_diff_density_rms         0.128
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_ac211
_database_code_depnum_ccdc_archive 'CCDC 1032673'
_audit_update_record             
;
2014-11-02 deposited with the CCDC.
2015-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H20 N4 O4'
_chemical_formula_weight         356.38

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/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                   4.8452(4)
_cell_length_b                   10.3656(10)
_cell_length_c                   17.3307(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.778(4)
_cell_angle_gamma                90.00
_cell_volume                     862.40(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1269
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      27.45

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             376
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.644
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   'Bruker SADABS (Bruker, 1999)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(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 D8 Venture'
_diffrn_measurement_method       'Phi and Omega Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8178
_diffrn_reflns_av_R_equivalents  0.0819
_diffrn_reflns_av_sigmaI/netI    0.0791
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         28.70
_reflns_number_total             2227
_reflns_number_gt                1374
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker ApexII'
_computing_cell_refinement       'Bruker Apex II'
_computing_data_reduction        'Bruker Apex II'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0596P)²+0.0324P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2227
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1137
_refine_ls_R_factor_gt           0.0546
_refine_ls_wR_factor_ref         0.1270
_refine_ls_wR_factor_gt          0.1075
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1A C 0.3515(4) 0.52446(18) 0.22594(11) 0.0159(4) Uani 1 1 d . . .
H1A H 0.2890 0.5800 0.2620 0.019 Uiso 1 1 calc R . .
C1B C 0.8649(3) 0.43240(17) 0.36591(11) 0.0137(4) Uani 1 1 d . . .
C2A C 0.5366(4) 0.57121(17) 0.17858(11) 0.0151(4) Uani 1 1 d . . .
H2A H 0.5964 0.6565 0.1829 0.018 Uiso 1 1 calc R . .
C2B C 0.6754(4) 0.39990(18) 0.42536(11) 0.0160(4) Uani 1 1 d . . .
H2B1 H 0.7710 0.3405 0.4632 0.019 Uiso 1 1 calc R . .
H2B2 H 0.5113 0.3564 0.3994 0.019 Uiso 1 1 calc R . .
C3A C 0.6322(3) 0.48977(17) 0.12461(10) 0.0127(4) Uani 1 1 d . . .
C3B C 0.5845(4) 0.51763(17) 0.46788(10) 0.0140(4) Uani 1 1 d . . .
H3B1 H 0.7483 0.5655 0.4901 0.017 Uiso 1 1 calc R . .
H3B2 H 0.4741 0.5734 0.4308 0.017 Uiso 1 1 calc R . .
C4A C 0.5347(4) 0.36335(17) 0.12008(11) 0.0159(4) Uani 1 1 d . . .
H4A H 0.5942 0.3060 0.0845 0.019 Uiso 1 1 calc R . .
C5A C 0.3491(4) 0.32403(17) 0.16899(11) 0.0160(4) Uani 1 1 d . . .
H5A H 0.2836 0.2396 0.1652 0.019 Uiso 1 1 calc R . .
C6A C 0.8268(3) 0.53886(18) 0.07366(10) 0.0137(4) Uani 1 1 d . . .
H6A H 0.8922 0.6231 0.0796 0.016 Uiso 1 1 calc R . .
N1A N 0.2585(3) 0.40288(15) 0.22208(9) 0.0141(4) Uani 1 1 d . . .
N2A N 0.9073(3) 0.46680(15) 0.02120(9) 0.0159(4) Uani 1 1 d . . .
O1B O 0.9219(3) 0.33145(12) 0.32357(8) 0.0189(3) Uani 1 1 d . . .
H1B H 1.0469 0.3587 0.2861 0.023 Uiso 1 1 d R . .
O2B O 0.9568(2) 0.53943(12) 0.35776(8) 0.0182(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1A N1A 1.337(2) . ?
C1A C2A 1.383(2) . ?
C1A H1A 0.9300 . ?
C1B O2B 1.211(2) . ?
C1B O1B 1.328(2) . ?
C1B C2B 1.508(2) . ?
C2A C3A 1.385(2) . ?
C2A H2A 0.9300 . ?
C2B C3B 1.521(2) . ?
C2B H2B1 0.9700 . ?
C2B H2B2 0.9700 . ?
C3A C4A 1.391(2) . ?
C3A C6A 1.468(2) . ?
C3B C3B 1.513(3) 3_666 ?
C3B H3B1 0.9700 . ?
C3B H3B2 0.9700 . ?
C4A C5A 1.378(2) . ?
C4A H4A 0.9300 . ?
C5A N1A 1.348(2) . ?
C5A H5A 0.9300 . ?
C6A N2A 1.278(2) . ?
C6A H6A 0.9300 . ?
N2A N2A 1.414(3) 3_765 ?
O1B H1B 0.9869 . ?

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
N1A C1A C2A 122.81(17) . . ?
N1A C1A H1A 118.6 . . ?
C2A C1A H1A 118.6 . . ?
O2B C1B O1B 123.38(16) . . ?
O2B C1B C2B 123.49(16) . . ?
O1B C1B C2B 113.12(15) . . ?
C1A C2A C3A 119.35(17) . . ?
C1A C2A H2A 120.3 . . ?
C3A C2A H2A 120.3 . . ?
C1B C2B C3B 113.25(15) . . ?
C1B C2B H2B1 108.9 . . ?
C3B C2B H2B1 108.9 . . ?
C1B C2B H2B2 108.9 . . ?
C3B C2B H2B2 108.9 . . ?
H2B1 C2B H2B2 107.7 . . ?
C2A C3A C4A 118.05(15) . . ?
C2A C3A C6A 119.71(16) . . ?
C4A C3A C6A 122.23(16) . . ?
C3B C3B C2B 112.56(19) 3_666 . ?
C3B C3B H3B1 109.1 3_666 . ?
C2B C3B H3B1 109.1 . . ?
C3B C3B H3B2 109.1 3_666 . ?
C2B C3B H3B2 109.1 . . ?
H3B1 C3B H3B2 107.8 . . ?
C5A C4A C3A 119.23(16) . . ?
C5A C4A H4A 120.4 . . ?
C3A C4A H4A 120.4 . . ?
N1A C5A C4A 122.71(17) . . ?
N1A C5A H5A 118.6 . . ?
C4A C5A H5A 118.6 . . ?
N2A C6A C3A 120.54(17) . . ?
N2A C6A H6A 119.7 . . ?
C3A C6A H6A 119.7 . . ?
C1A N1A C5A 117.83(14) . . ?
C6A N2A N2A 111.19(19) . 3_765 ?
C1B O1B H1B 109.3 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        28.70
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.065
####################################################################### 
# 
# 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_a21061_0m
_database_code_depnum_ccdc_archive 'CCDC 1032674'
_audit_update_record             
;
2014-11-04 deposited with the CCDC.
2015-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H18 N4 O4'
_chemical_formula_weight         342.35

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   C2/c

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

_cell_length_a                   40.33(9)
_cell_length_b                   4.629(13)
_cell_length_c                   20.38(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 117.50(3)
_cell_angle_gamma                90.00
_cell_volume                     3375(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1819
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      24.56

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1440
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.509
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   'Bruker SADABS (Bruker, 1999)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Axs APEX automatic diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2480
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_av_sigmaI/netI    0.1183
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         20.84
_reflns_number_total             1506
_reflns_number_gt                770
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0929P)²+0.0000P] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1506
_refine_ls_number_parameters     234
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1474
_refine_ls_R_factor_gt           0.0772
_refine_ls_wR_factor_ref         0.2322
_refine_ls_wR_factor_gt          0.1756
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_restrained_S_all      0.990
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1A C 0.7662(3) 0.0857(19) 0.5929(5) 0.038(3) Uani 1 1 d . . .
H1A H 0.7541 0.0012 0.5463 0.045 Uiso 1 1 calc R . .
C1B C 0.8197(3) 0.9162(19) 0.4544(5) 0.036(3) Uani 1 1 d . . .
C2A C 0.7940(2) 0.2900(19) 0.6063(4) 0.033(3) Uani 1 1 d . . .
H2A H 0.8008 0.3367 0.5697 0.039 Uiso 1 1 calc R . .
C2B C 0.8538(3) 1.1013(19) 0.4656(5) 0.043(3) Uani 1 1 d . . .
H2B1 H 0.8706 0.9821 0.4552 0.051 Uiso 1 1 calc R . .
H2B2 H 0.8452 1.2570 0.4297 0.051 Uiso 1 1 calc R . .
C3A C 0.8113(2) 0.4219(18) 0.6749(4) 0.032(3) Uani 1 1 d . . .
C3B C 0.8758(3) 1.2317(19) 0.5425(5) 0.044(3) Uani 1 1 d . . .
H3B1 H 0.8828 1.0785 0.5790 0.052 Uiso 1 1 calc R . .
H3B2 H 0.8598 1.3647 0.5515 0.052 Uiso 1 1 calc R . .
C4A C 0.8012(3) 0.3384(18) 0.7290(5) 0.038(3) Uani 1 1 d . . .
H4A H 0.8124 0.4210 0.7759 0.045 Uiso 1 1 calc R . .
C4B C 0.9114(3) 1.3935(19) 0.5534(4) 0.038(3) Uani 1 1 d . . .
H4B1 H 0.9059 1.5140 0.5107 0.046 Uiso 1 1 calc R . .
H4B2 H 0.9202 1.5168 0.5967 0.046 Uiso 1 1 calc R . .
C5A C 0.7741(2) 0.1300(19) 0.7105(5) 0.036(3) Uani 1 1 d . . .
H5A H 0.7678 0.0696 0.7468 0.044 Uiso 1 1 calc R . .
C5B C 0.9411(3) 1.1757(19) 0.5631(6) 0.044(3) Uani 1 1 d . . .
C6A C 0.8400(2) 0.6429(19) 0.6891(5) 0.037(3) Uani 1 1 d . . .
H6A H 0.8451 0.6999 0.6510 0.044 Uiso 1 1 calc R . .
C7A C 0.9033(3) 1.0785(18) 0.8170(5) 0.036(3) Uani 1 1 d . . .
H7A H 0.8998 1.0187 0.8569 0.043 Uiso 1 1 calc R . .
C8A C 0.9778(3) 1.6499(19) 0.9010(5) 0.039(3) Uani 1 1 d . . .
H8A H 0.9908 1.7422 0.9464 0.046 Uiso 1 1 calc R . .
C9A C 0.9519(3) 1.4392(19) 0.8945(5) 0.041(3) Uani 1 1 d . . .
H9A H 0.9482 1.3890 0.9349 0.049 Uiso 1 1 calc R . .
C10A C 0.9313(2) 1.3033(18) 0.8255(5) 0.035(3) Uani 1 1 d . . .
C11A C 0.9381(3) 1.3858(19) 0.7683(5) 0.038(3) Uani 1 1 d . . .
H11A H 0.9253 1.2989 0.7221 0.046 Uiso 1 1 calc R . .
C12A C 0.9645(3) 1.601(2) 0.7798(5) 0.046(3) Uani 1 1 d . . .
H12A H 0.9681 1.6610 0.7400 0.056 Uiso 1 1 calc R . .
N1A N 0.7562(2) 0.0074(15) 0.6431(4) 0.038(2) Uani 1 1 d . . .
N2A N 0.8581(2) 0.7589(15) 0.7533(4) 0.037(2) Uani 1 1 d . . .
N3A N 0.8841(2) 0.9702(16) 0.7522(4) 0.036(2) Uani 1 1 d . . .
N4A N 0.9850(2) 1.7262(15) 0.8468(4) 0.039(2) Uani 1 1 d . . .
O1B O 0.8006(2) 0.8431(15) 0.3840(3) 0.051(2) Uani 1 1 d D . .
O2B O 0.81326(18) 0.8522(13) 0.5042(3) 0.0465(19) Uani 1 1 d . . .
O3B O 0.94538(17) 1.0751(13) 0.5130(3) 0.048(2) Uani 1 1 d . . .
O4B O 0.9629(2) 1.1098(14) 0.6346(3) 0.047(2) Uani 1 1 d D . .
H4B H 0.978(2) 0.978(17) 0.636(6) 0.08(5) Uiso 1 1 d D . .
H1B H 0.7826(15) 0.730(14) 0.379(4) 0.02(3) Uiso 1 1 d D . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1A N1A 1.311(11) . ?
C1A C2A 1.395(11) . ?
C1B O2B 1.194(10) . ?
C1B O1B 1.321(10) . ?
C1B C2B 1.547(12) . ?
C2A C3A 1.384(11) . ?
C2B C3B 1.524(12) . ?
C3A C4A 1.397(11) . ?
C3A C6A 1.468(12) . ?
C3B C4B 1.541(11) . ?
C4A C5A 1.373(11) . ?
C4B C5B 1.507(13) . ?
C5A N1A 1.348(10) . ?
C5B O3B 1.206(11) . ?
C5B O4B 1.343(11) . ?
C6A N2A 1.285(10) . ?
C7A N3A 1.284(10) . ?
C7A C10A 1.486(12) . ?
C8A N4A 1.314(11) . ?
C8A C9A 1.390(12) . ?
C9A C10A 1.408(12) . ?
C10A C11A 1.371(12) . ?
C11A C12A 1.395(12) . ?
C12A N4A 1.358(11) . ?
N2A N3A 1.444(9) . ?

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
N1A C1A C2A 122.9(8) . . ?
O2B C1B O1B 127.8(10) . . ?
O2B C1B C2B 122.6(8) . . ?
O1B C1B C2B 109.6(8) . . ?
C3A C2A C1A 118.8(8) . . ?
C3B C2B C1B 115.2(8) . . ?
C2A C3A C4A 118.7(9) . . ?
C2A C3A C6A 119.4(8) . . ?
C4A C3A C6A 121.8(8) . . ?
C2B C3B C4B 113.6(8) . . ?
C5A C4A C3A 117.6(8) . . ?
C5B C4B C3B 108.9(8) . . ?
N1A C5A C4A 124.0(9) . . ?
O3B C5B O4B 123.6(10) . . ?
O3B C5B C4B 124.3(9) . . ?
O4B C5B C4B 112.1(9) . . ?
N2A C6A C3A 121.2(9) . . ?
N3A C7A C10A 117.3(8) . . ?
N4A C8A C9A 123.8(9) . . ?
C8A C9A C10A 118.7(9) . . ?
C11A C10A C9A 117.9(10) . . ?
C11A C10A C7A 122.4(8) . . ?
C9A C10A C7A 119.7(9) . . ?
C10A C11A C12A 119.5(9) . . ?
N4A C12A C11A 122.5(9) . . ?
C1A N1A C5A 117.8(8) . . ?
C6A N2A N3A 110.0(8) . . ?
C7A N3A N2A 110.2(8) . . ?
C8A N4A C12A 117.5(9) . . ?

_diffrn_measured_fraction_theta_max 0.846
_diffrn_reflns_theta_full        20.84
_diffrn_measured_fraction_theta_full 0.846
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.067
