# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2008

data_global

_journal_coden_Cambridge         1350
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

loop_
_publ_author_name
'Andrew Bond'
'Signe Skovsgaard'

_publ_contact_author_name        'Andrew Bond'
_publ_contact_author_email       ADB@CHEM.SDU.DK

_publ_section_title              
;
Co-crystallisation of benzoic acid derivatives with
N-containing bases in solution and by mechanical grinding:
stoichiometric variants, polymorphism and twinning
;

# Attachment 'submit.cif'

#=============================================================================

data_1a
_database_code_depnum_ccdc_archive 'CCDC 692776'

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C7 H5 O2 -), C6 H14 N2 2+'
_chemical_formula_sum            'C20 H24 N2 O4'
_chemical_formula_weight         356.41
_chemical_absolute_configuration unk

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 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   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   12.4505(15)
_cell_length_b                   24.448(3)
_cell_length_c                   19.153(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.069(4)
_cell_angle_gamma                90.00
_cell_volume                     5655.1(11)
_cell_formula_units_Z            12
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    3199
_cell_measurement_theta_min      3.33
_cell_measurement_theta_max      19.17

_exptl_crystal_description       lath
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2280
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.715
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_process_details   
;
SADABS v.2.10 (Sheldrick, 2003)
Ratio of minimum to maximum apparent transmission: 0.716763
;

_exptl_special_details           
;
H atoms between DABCO and acid visible in difference Fourier maps,
in positions approximately equidistant from the N and O atoms
involved. On average, they are marginally closer to N. Would also
expect proton transfer on grounds of pKa values. These H atoms
are placed geometrically on N for the final refinement.

The structure appears to be very close to P21/m. However, all
attempts to refine in P21/m fail, with enormous R-factors.
;

_diffrn_ambient_temperature      180(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-Nonius X8APEX-II CCD'
_diffrn_measurement_method       'thin-slice ω and φ scans'
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            85735
_diffrn_reflns_av_R_equivalents  0.1043
_diffrn_reflns_av_sigmaI/netI    0.1389
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.55
_diffrn_reflns_theta_max         25.74
_diffrn_measured_fraction_theta_max 0.965
_diffrn_reflns_theta_full        25.74
_diffrn_measured_fraction_theta_full 0.965
_reflns_number_total             10699
_reflns_number_gt                4929
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 v.1.0-22 (Bruker Nonius, 2004)'
_computing_cell_refinement       'SAINT v.7.06a (Bruker, 2003)'
_computing_data_reduction        'SAINT v.7.06a'
_computing_structure_solution    'SHELXTL v.6.10 (Sheldrick, 2000)'
_computing_structure_refinement  'SHELXTL v.6.10'
_computing_molecular_graphics    'SHELXTL v.6.10'
_computing_publication_material  'SHELXTL v.6.10'

_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)+(0.1077P)²] 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_abs_structure_details 
;
In the absence of significant anomalous scattering effects,
Friedel pairs have been merged as equivalent data
;
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_reflns         10699
_refine_ls_number_parameters     1405
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1856
_refine_ls_R_factor_gt           0.0636
_refine_ls_wR_factor_ref         0.1978
_refine_ls_wR_factor_gt          0.1519
_refine_ls_goodness_of_fit_ref   0.947
_refine_ls_restrained_S_all      0.947
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.065

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
O11 O 0.8918(4) 0.6537(3) 1.0298(3) 0.0512(17) Uani 1 1 d . . .
O12 O 0.7525(4) 0.6599(2) 1.0848(3) 0.0415(15) Uani 1 1 d . . .
C11 C 0.9111(6) 0.7127(3) 1.1309(4) 0.0252(19) Uani 1 1 d . . .
C12 C 1.0228(6) 0.7278(3) 1.1263(5) 0.039(2) Uani 1 1 d . . .
H12 H 1.0558 0.7129 1.0907 0.047 Uiso 1 1 calc R . .
C13 C 1.0791(8) 0.7660(4) 1.1783(5) 0.049(3) Uani 1 1 d . . .
H13 H 1.1513 0.7773 1.1763 0.059 Uiso 1 1 calc R . .
C14 C 1.0365(9) 0.7865(4) 1.2288(6) 0.060(3) Uani 1 1 d . . .
H14 H 1.0771 0.8127 1.2614 0.072 Uiso 1 1 calc R . .
C15 C 0.9306(8) 0.7698(4) 1.2350(5) 0.062(3) Uani 1 1 d . . .
H15 H 0.9005 0.7838 1.2724 0.074 Uiso 1 1 calc R . .
C16 C 0.8704(7) 0.7322(4) 1.1849(4) 0.044(2) Uani 1 1 d . . .
H16 H 0.7997 0.7203 1.1894 0.052 Uiso 1 1 calc R . .
C17 C 0.8507(7) 0.6720(3) 1.0766(4) 0.031(2) Uani 1 1 d . . .
O21 O 0.2618(5) 0.6526(3) 1.1170(3) 0.0520(17) Uani 1 1 d . . .
O22 O 0.3322(4) 0.6675(2) 1.0229(3) 0.0437(15) Uani 1 1 d . . .
C21 C 0.4117(6) 0.7143(3) 1.1309(5) 0.029(2) Uani 1 1 d . . .
C22 C 0.4978(7) 0.7346(3) 1.1011(4) 0.039(2) Uani 1 1 d . . .
H22 H 0.5028 0.7236 1.0544 0.047 Uiso 1 1 calc R . .
C23 C 0.5765(8) 0.7715(4) 1.1426(5) 0.055(3) Uani 1 1 d . . .
H23 H 0.6307 0.7878 1.1219 0.066 Uiso 1 1 calc R . .
C24 C 0.5745(8) 0.7832(4) 1.2106(6) 0.048(3) Uani 1 1 d . . .
H24 H 0.6290 0.8071 1.2379 0.058 Uiso 1 1 calc R . .
C25 C 0.4954(9) 0.7615(4) 1.2417(6) 0.061(3) Uani 1 1 d . . .
H25 H 0.4955 0.7701 1.2901 0.073 Uiso 1 1 calc R . .
C26 C 0.4150(7) 0.7268(4) 1.2012(5) 0.044(2) Uani 1 1 d . . .
H26 H 0.3610 0.7113 1.2229 0.053 Uiso 1 1 calc R . .
C27 C 0.3303(7) 0.6744(3) 1.0894(5) 0.034(2) Uani 1 1 d . . .
O31 O 0.7741(5) 0.6572(3) 0.4452(3) 0.0580(17) Uani 1 1 d . . .
O32 O 0.8675(5) 0.6570(3) 0.3600(3) 0.0606(18) Uani 1 1 d . . .
C31 C 0.9306(7) 0.7143(3) 0.4600(5) 0.039(2) Uani 1 1 d . . .
C32 C 1.0156(7) 0.7351(3) 0.4301(5) 0.040(2) Uani 1 1 d . . .
H32 H 1.0225 0.7227 0.3843 0.049 Uiso 1 1 calc R . .
C33 C 1.0883(8) 0.7735(4) 0.4675(6) 0.064(3) Uani 1 1 d . . .
H33 H 1.1415 0.7897 0.4458 0.077 Uiso 1 1 calc R . .
C34 C 1.0843(8) 0.7883(4) 0.5355(6) 0.058(3) Uani 1 1 d . . .
H34 H 1.1377 0.8130 0.5622 0.070 Uiso 1 1 calc R . .
C35 C 1.0058(9) 0.7683(5) 0.5646(6) 0.071(3) Uani 1 1 d . . .
H35 H 1.0026 0.7802 0.6113 0.086 Uiso 1 1 calc R . .
C36 C 0.9282(7) 0.7304(4) 0.5286(5) 0.049(2) Uani 1 1 d . . .
H36 H 0.8743 0.7159 0.5511 0.058 Uiso 1 1 calc R . .
C37 C 0.8505(7) 0.6732(3) 0.4189(5) 0.040(2) Uani 1 1 d . . .
O41 O 0.4261(4) 0.6586(3) 0.3519(3) 0.0599(18) Uani 1 1 d . . .
O42 O 0.2825(4) 0.6588(2) 0.4024(3) 0.0467(16) Uani 1 1 d . . .
C41 C 0.4313(8) 0.7155(3) 0.4531(5) 0.039(2) Uani 1 1 d . . .
C42 C 0.5442(6) 0.7305(3) 0.4555(4) 0.036(2) Uani 1 1 d . . .
H42 H 0.5830 0.7162 0.4226 0.043 Uiso 1 1 calc R . .
C43 C 0.5939(9) 0.7688(4) 0.5109(6) 0.059(3) Uani 1 1 d . . .
H43 H 0.6670 0.7812 0.5132 0.071 Uiso 1 1 calc R . .
C44 C 0.5428(9) 0.7873(4) 0.5586(5) 0.059(3) Uani 1 1 d . . .
H44 H 0.5793 0.8133 0.5932 0.071 Uiso 1 1 calc R . .
C45 C 0.4362(8) 0.7699(4) 0.5602(6) 0.068(3) Uani 1 1 d . . .
H45 H 0.4017 0.7820 0.5965 0.082 Uiso 1 1 calc R . .
C46 C 0.3824(7) 0.7337(4) 0.5058(5) 0.047(2) Uani 1 1 d . . .
H46 H 0.3099 0.7215 0.5054 0.057 Uiso 1 1 calc R . .
C47 C 0.3786(8) 0.6753(3) 0.3976(4) 0.036(2) Uani 1 1 d . . .
O51 O 0.8723(5) 0.6869(3) 0.6776(3) 0.0628(18) Uani 1 1 d . . .
O52 O 0.7782(5) 0.6557(2) 0.7546(3) 0.0484(16) Uani 1 1 d . . .
C51 C 0.9207(6) 0.7176(3) 0.7975(5) 0.029(2) Uani 1 1 d . . .
C52 C 1.0244(7) 0.7380(3) 0.7906(5) 0.051(3) Uani 1 1 d . . .
H52 H 1.0503 0.7301 0.7489 0.061 Uiso 1 1 calc R . .
C53 C 1.0885(8) 0.7703(4) 0.8471(7) 0.062(3) Uani 1 1 d . . .
H53 H 1.1536 0.7877 0.8406 0.075 Uiso 1 1 calc R . .
C54 C 1.0596(10) 0.7768(4) 0.9090(7) 0.082(4) Uani 1 1 d . . .
H54 H 1.1059 0.7975 0.9464 0.098 Uiso 1 1 calc R . .
C55 C 0.9607(8) 0.7533(4) 0.9201(5) 0.058(3) Uani 1 1 d . . .
H55 H 0.9401 0.7571 0.9645 0.070 Uiso 1 1 calc R . .
C56 C 0.8947(7) 0.7241(3) 0.8618(4) 0.043(2) Uani 1 1 d . . .
H56 H 0.8281 0.7081 0.8679 0.051 Uiso 1 1 calc R . .
C57 C 0.8541(6) 0.6841(4) 0.7374(5) 0.036(2) Uani 1 1 d . . .
O61 O 0.4139(4) 0.6501(3) 0.6918(3) 0.0609(19) Uani 1 1 d . . .
O62 O 0.2665(5) 0.6614(2) 0.7372(3) 0.0455(15) Uani 1 1 d . . .
C61 C 0.4236(7) 0.7113(3) 0.7896(5) 0.035(2) Uani 1 1 d . . .
C62 C 0.5289(7) 0.7311(3) 0.7835(4) 0.039(2) Uani 1 1 d . . .
H62 H 0.5607 0.7197 0.7455 0.047 Uiso 1 1 calc R . .
C63 C 0.5842(8) 0.7690(4) 0.8371(6) 0.060(3) Uani 1 1 d . . .
H63 H 0.6536 0.7836 0.8340 0.073 Uiso 1 1 calc R . .
C64 C 0.5409(10) 0.7843(4) 0.8916(6) 0.060(3) Uani 1 1 d . . .
H64 H 0.5779 0.8107 0.9254 0.072 Uiso 1 1 calc R . .
C65 C 0.4403(8) 0.7614(4) 0.8988(5) 0.059(3) Uani 1 1 d . . .
H65 H 0.4114 0.7704 0.9390 0.070 Uiso 1 1 calc R . .
C66 C 0.3846(7) 0.7258(3) 0.8468(4) 0.038(2) Uani 1 1 d . . .
H66 H 0.3162 0.7108 0.8514 0.046 Uiso 1 1 calc R . .
C67 C 0.3670(7) 0.6715(3) 0.7345(4) 0.034(2) Uani 1 1 d . . .
O71 O 0.3240(5) 0.4797(3) 0.8135(3) 0.0597(18) Uani 1 1 d . . .
O72 O 0.4661(4) 0.4807(2) 0.7629(3) 0.0424(15) Uani 1 1 d . . .
C71 C 0.3080(6) 0.4270(3) 0.7094(4) 0.028(2) Uani 1 1 d . . .
C72 C 0.2040(8) 0.4090(3) 0.7042(4) 0.045(2) Uani 1 1 d . . .
H72 H 0.1698 0.4198 0.7413 0.055 Uiso 1 1 calc R . .
C73 C 0.1439(8) 0.3771(4) 0.6516(5) 0.043(2) Uani 1 1 d . . .
H73 H 0.0698 0.3668 0.6502 0.051 Uiso 1 1 calc R . .
C74 C 0.1983(9) 0.3599(4) 0.5986(6) 0.056(3) Uani 1 1 d . . .
H74 H 0.1602 0.3377 0.5598 0.067 Uiso 1 1 calc R . .
C75 C 0.3054(9) 0.3751(4) 0.6029(5) 0.056(3) Uani 1 1 d . . .
H75 H 0.3420 0.3615 0.5684 0.067 Uiso 1 1 calc R . .
C76 C 0.3603(8) 0.4092(3) 0.6553(5) 0.046(2) Uani 1 1 d . . .
H76 H 0.4332 0.4211 0.6559 0.055 Uiso 1 1 calc R . .
C77 C 0.3677(7) 0.4647(4) 0.7662(5) 0.035(2) Uani 1 1 d . . .
O81 O -0.0277(5) 0.4850(3) 0.7174(3) 0.0575(18) Uani 1 1 d . . .
O82 O -0.1152(5) 0.4810(3) 0.8057(3) 0.0549(17) Uani 1 1 d . . .
C81 C -0.1880(6) 0.4288(3) 0.7014(4) 0.027(2) Uani 1 1 d . . .
C82 C -0.2672(7) 0.4082(4) 0.7321(5) 0.046(2) Uani 1 1 d . . .
H82A H -0.2668 0.4174 0.7804 0.055 Uiso 1 1 calc R . .
C83 C -0.3471(8) 0.3742(4) 0.6936(5) 0.055(3) Uani 1 1 d . . .
H83 H -0.4040 0.3611 0.7145 0.066 Uiso 1 1 calc R . .
C84 C -0.3454(8) 0.3590(4) 0.6254(5) 0.055(3) Uani 1 1 d . . .
H84 H -0.4007 0.3350 0.5992 0.066 Uiso 1 1 calc R . .
C85 C -0.2630(8) 0.3785(4) 0.5938(5) 0.044(2) Uani 1 1 d . . .
H85 H -0.2610 0.3674 0.5466 0.052 Uiso 1 1 calc R . .
C86 C -0.1850(7) 0.4139(3) 0.6318(4) 0.040(2) Uani 1 1 d . . .
H86 H -0.1292 0.4281 0.6107 0.048 Uiso 1 1 calc R . .
C87 C -0.1007(7) 0.4672(4) 0.7421(5) 0.036(2) Uani 1 1 d . . .
O91 O 0.4904(5) 0.4838(3) 0.0521(3) 0.0607(18) Uani 1 1 d . . .
O92 O 0.4183(4) 0.4686(2) 0.1447(3) 0.0494(16) Uani 1 1 d . . .
C91 C 0.3335(7) 0.4250(3) 0.0355(4) 0.031(2) Uani 1 1 d . . .
C92 C 0.2534(7) 0.4043(4) 0.0630(5) 0.040(2) Uani 1 1 d . . .
H92 H 0.2545 0.4118 0.1118 0.048 Uiso 1 1 calc R . .
C93 C 0.1705(7) 0.3729(4) 0.0239(5) 0.053(3) Uani 1 1 d . . .
H93 H 0.1110 0.3612 0.0433 0.064 Uiso 1 1 calc R . .
C94 C 0.1753(8) 0.3584(4) -0.0456(6) 0.062(3) Uani 1 1 d . . .
H94 H 0.1196 0.3353 -0.0733 0.075 Uiso 1 1 calc R . .
C95 C 0.2584(8) 0.3767(3) -0.0744(5) 0.040(2) Uani 1 1 d . . .
H95 H 0.2601 0.3667 -0.1220 0.048 Uiso 1 1 calc R . .
C96 C 0.3392(7) 0.4096(3) -0.0346(4) 0.035(2) Uani 1 1 d . . .
H96 H 0.3984 0.4220 -0.0539 0.042 Uiso 1 1 calc R . .
C97 C 0.4243(7) 0.4618(3) 0.0796(5) 0.038(2) Uani 1 1 d . . .
O101 O -0.1387(4) 0.4790(3) 0.1401(3) 0.0528(17) Uani 1 1 d . . .
O102 O -0.0028(4) 0.4767(2) 0.0849(3) 0.0453(16) Uani 1 1 d . . .
C101 C -0.1677(8) 0.4259(4) 0.0355(4) 0.036(2) Uani 1 1 d . . .
C102 C -0.2661(8) 0.4050(4) 0.0395(5) 0.046(2) Uani 1 1 d . . .
H102 H -0.2917 0.4134 0.0811 0.055 Uiso 1 1 calc R . .
C103 C -0.3317(9) 0.3727(4) -0.0114(5) 0.051(3) Uani 1 1 d . . .
H103 H -0.4028 0.3609 -0.0078 0.062 Uiso 1 1 calc R . .
C104 C -0.2868(8) 0.3578(4) -0.0706(6) 0.052(3) Uani 1 1 d . . .
H104 H -0.3292 0.3353 -0.1077 0.063 Uiso 1 1 calc R . .
C105 C -0.1858(8) 0.3747(3) -0.0750(5) 0.049(3) Uani 1 1 d . . .
H105 H -0.1560 0.3627 -0.1136 0.058 Uiso 1 1 calc R . .
C106 C -0.1267(7) 0.4090(3) -0.0242(4) 0.037(2) Uani 1 1 d . . .
H106 H -0.0567 0.4219 -0.0286 0.044 Uiso 1 1 calc R . .
C107 C -0.1004(7) 0.4626(4) 0.0899(4) 0.038(2) Uani 1 1 d . . .
C111 C 0.3214(7) 0.4298(3) 0.3810(4) 0.027(2) Uani 1 1 d . . .
O111 O 0.3384(5) 0.4918(3) 0.4777(3) 0.0558(17) Uani 1 1 d . . .
O112 O 0.4839(4) 0.4821(2) 0.4314(3) 0.0413(14) Uani 1 1 d . . .
C112 C 0.2284(8) 0.4045(4) 0.3901(6) 0.056(3) Uani 1 1 d . . .
H112 H 0.2034 0.4122 0.4322 0.067 Uiso 1 1 calc R . .
C113 C 0.1699(9) 0.3683(4) 0.3408(7) 0.073(3) Uani 1 1 d . . .
H113 H 0.1038 0.3519 0.3473 0.088 Uiso 1 1 calc R . .
C114 C 0.2109(9) 0.3562(4) 0.2798(6) 0.063(3) Uani 1 1 d . . .
H114 H 0.1708 0.3318 0.2443 0.076 Uiso 1 1 calc R . .
C115 C 0.3031(9) 0.3778(3) 0.2713(5) 0.054(3) Uani 1 1 d . . .
H115 H 0.3302 0.3679 0.2308 0.065 Uiso 1 1 calc R . .
C116 C 0.3615(7) 0.4149(3) 0.3205(4) 0.039(2) Uani 1 1 d . . .
H116 H 0.4283 0.4304 0.3137 0.047 Uiso 1 1 calc R . .
C117 C 0.3845(8) 0.4713(4) 0.4334(5) 0.041(2) Uani 1 1 d . . .
O121 O -0.1311(5) 0.4612(3) 0.4872(3) 0.0629(19) Uani 1 1 d . . .
O122 O -0.0257(4) 0.4860(2) 0.4147(3) 0.0412(15) Uani 1 1 d . . .
C121 C -0.1776(7) 0.4245(3) 0.3695(4) 0.034(2) Uani 1 1 d . . .
C122 C -0.2763(8) 0.4037(4) 0.3729(5) 0.046(2) Uani 1 1 d . . .
H122 H -0.3015 0.4097 0.4152 0.055 Uiso 1 1 calc R . .
C123 C -0.3420(9) 0.3742(4) 0.3182(6) 0.053(3) Uani 1 1 d . . .
H123 H -0.4144 0.3632 0.3199 0.063 Uiso 1 1 calc R . .
C124 C -0.2985(10) 0.3609(4) 0.2597(6) 0.067(3) Uani 1 1 d . . .
H124 H -0.3400 0.3395 0.2211 0.080 Uiso 1 1 calc R . .
C125 C -0.1970(10) 0.3789(4) 0.2587(6) 0.075(3) Uani 1 1 d . . .
H125 H -0.1678 0.3683 0.2193 0.090 Uiso 1 1 calc R . .
C126 C -0.1337(8) 0.4107(3) 0.3094(5) 0.047(2) Uani 1 1 d . . .
H126 H -0.0633 0.4235 0.3056 0.056 Uiso 1 1 calc R . .
C127 C -0.1090(7) 0.4588(3) 0.4297(4) 0.033(2) Uani 1 1 d . . .
N131 N 0.6547(5) 0.6022(2) 0.9767(3) 0.0252(15) Uani 1 1 d . . .
H13M H 0.6873 0.6230 1.0169 0.038 Uiso 1 1 calc R . .
N132 N 0.5637(5) 0.5458(3) 0.8681(3) 0.0294(16) Uani 1 1 d . . .
H13N H 0.5296 0.5252 0.8279 0.044 Uiso 1 1 calc R . .
C131 C 0.5335(5) 0.6000(3) 0.9685(4) 0.040(2) Uani 1 1 d . . .
H13B H 0.5035 0.6375 0.9682 0.048 Uiso 1 1 calc R . .
H13A H 0.5168 0.5798 1.0095 0.048 Uiso 1 1 calc R . .
C132 C 0.4802(6) 0.5712(3) 0.8985(4) 0.043(2) Uani 1 1 d . . .
H13C H 0.4281 0.5430 0.9074 0.051 Uiso 1 1 calc R . .
H13D H 0.4376 0.5980 0.8638 0.051 Uiso 1 1 calc R . .
C133 C 0.6335(6) 0.5888(3) 0.8468(4) 0.039(2) Uani 1 1 d . . .
H13F H 0.5892 0.6099 0.8057 0.047 Uiso 1 1 calc R . .
H13E H 0.6962 0.5717 0.8316 0.047 Uiso 1 1 calc R . .
C134 C 0.6780(6) 0.6276(3) 0.9113(4) 0.036(2) Uani 1 1 d . . .
H13H H 0.7587 0.6330 0.9182 0.043 Uiso 1 1 calc R . .
H13G H 0.6411 0.6636 0.9022 0.043 Uiso 1 1 calc R . .
C135 C 0.7010(6) 0.5454(3) 0.9855(4) 0.0372(19) Uani 1 1 d . . .
H13I H 0.6947 0.5299 1.0321 0.045 Uiso 1 1 calc R . .
H13J H 0.7803 0.5460 0.9848 0.045 Uiso 1 1 calc R . .
C136 C 0.6347(6) 0.5097(3) 0.9226(4) 0.040(2) Uani 1 1 d . . .
H13L H 0.6864 0.4891 0.9005 0.048 Uiso 1 1 calc R . .
H13K H 0.5883 0.4831 0.9409 0.048 Uiso 1 1 calc R . .
N141 N 0.1852(5) 0.6031(3) 0.9551(3) 0.0330(17) Uani 1 1 d . . .
H14M H 0.2390 0.6256 0.9832 0.050 Uiso 1 1 calc R . .
N142 N 0.0401(5) 0.5420(3) 0.8790(3) 0.0296(16) Uani 1 1 d . . .
H14N H -0.0138 0.5196 0.8510 0.044 Uiso 1 1 calc R . .
C141 C 0.0775(5) 0.6139(3) 0.9705(4) 0.047(2) Uani 1 1 d . . .
H14B H 0.0569 0.6527 0.9598 0.057 Uiso 1 1 calc R . .
H14A H 0.0824 0.6074 1.0222 0.057 Uiso 1 1 calc R . .
C142 C -0.0114(6) 0.5766(3) 0.9247(4) 0.047(2) Uani 1 1 d . . .
H14C H -0.0445 0.5534 0.9564 0.056 Uiso 1 1 calc R . .
H14D H -0.0710 0.5990 0.8943 0.056 Uiso 1 1 calc R . .
C143 C 0.0870(7) 0.5770(3) 0.8315(4) 0.050(2) Uani 1 1 d . . .
H14E H 0.0281 0.6003 0.8020 0.060 Uiso 1 1 calc R . .
H14F H 0.1178 0.5539 0.7986 0.060 Uiso 1 1 calc R . .
C144 C 0.1784(6) 0.6129(3) 0.8769(4) 0.0392(19) Uani 1 1 d . . .
H14G H 0.2502 0.6039 0.8661 0.047 Uiso 1 1 calc R . .
H14H H 0.1619 0.6519 0.8652 0.047 Uiso 1 1 calc R . .
C145 C 0.2149(5) 0.5451(3) 0.9706(4) 0.0344(18) Uani 1 1 d . . .
H14I H 0.2190 0.5372 1.0219 0.041 Uiso 1 1 calc R . .
H14J H 0.2886 0.5378 0.9617 0.041 Uiso 1 1 calc R . .
C146 C 0.1283(6) 0.5076(3) 0.9228(4) 0.044(2) Uani 1 1 d . . .
H14L H 0.1632 0.4854 0.8912 0.053 Uiso 1 1 calc R . .
H14K H 0.0967 0.4824 0.9531 0.053 Uiso 1 1 calc R . .
N151 N 0.7120(5) 0.5963(3) 0.2897(3) 0.0370(18) Uani 1 1 d . . .
H15M H 0.7658 0.6191 0.3170 0.055 Uiso 1 1 calc R . .
N152 N 0.5660(5) 0.5343(3) 0.2146(3) 0.0352(18) Uani 1 1 d . . .
H15N H 0.5116 0.5117 0.1873 0.053 Uiso 1 1 calc R . .
C151 C 0.6624(6) 0.5630(3) 0.3370(4) 0.045(2) Uani 1 1 d . . .
H15B H 0.6309 0.5870 0.3686 0.054 Uiso 1 1 calc R . .
H15A H 0.7197 0.5396 0.3677 0.054 Uiso 1 1 calc R . .
C152 C 0.5708(5) 0.5272(3) 0.2910(4) 0.043(2) Uani 1 1 d . . .
H15C H 0.5855 0.4883 0.3043 0.052 Uiso 1 1 calc R . .
H15D H 0.4986 0.5373 0.3004 0.052 Uiso 1 1 calc R . .
C153 C 0.6760(5) 0.5194(3) 0.2025(4) 0.041(2) Uani 1 1 d . . .
H15F H 0.6736 0.5214 0.1505 0.049 Uiso 1 1 calc R . .
H15E H 0.6951 0.4814 0.2189 0.049 Uiso 1 1 calc R . .
C154 C 0.7633(6) 0.5588(3) 0.2443(4) 0.050(2) Uani 1 1 d . . .
H15H H 0.8245 0.5379 0.2756 0.060 Uiso 1 1 calc R . .
H15G H 0.7941 0.5807 0.2103 0.060 Uiso 1 1 calc R . .
C155 C 0.6281(6) 0.6287(3) 0.2413(4) 0.042(2) Uani 1 1 d . . .
H15J H 0.6635 0.6523 0.2114 0.051 Uiso 1 1 calc R . .
H15I H 0.5903 0.6525 0.2696 0.051 Uiso 1 1 calc R . .
C156 C 0.5430(6) 0.5909(3) 0.1925(4) 0.038(2) Uani 1 1 d . . .
H15K H 0.4674 0.6008 0.1959 0.046 Uiso 1 1 calc R . .
H15L H 0.5470 0.5954 0.1418 0.046 Uiso 1 1 calc R . .
N161 N 0.1845(5) 0.5931(3) 0.3011(3) 0.0297(17) Uani 1 1 d . . .
H16M H 0.2172 0.6146 0.3406 0.045 Uiso 1 1 calc R . .
N162 N 0.0958(5) 0.5340(3) 0.1923(3) 0.0384(18) Uani 1 1 d . . .
H16N H 0.0612 0.5127 0.1529 0.058 Uiso 1 1 calc R . .
C161 C 0.1186(6) 0.5486(3) 0.3223(4) 0.0315(19) Uani 1 1 d . . .
H16B H 0.0546 0.5642 0.3376 0.038 Uiso 1 1 calc R . .
H16A H 0.1647 0.5282 0.3634 0.038 Uiso 1 1 calc R . .
C162 C 0.0779(6) 0.5103(3) 0.2596(4) 0.035(2) Uani 1 1 d . . .
H16C H 0.1178 0.4750 0.2694 0.042 Uiso 1 1 calc R . .
H16D H -0.0020 0.5030 0.2538 0.042 Uiso 1 1 calc R . .
C163 C 0.2156(5) 0.5366(3) 0.1983(4) 0.037(2) Uani 1 1 d . . .
H16F H 0.2302 0.5570 0.1569 0.044 Uiso 1 1 calc R . .
H16E H 0.2460 0.4992 0.1980 0.044 Uiso 1 1 calc R . .
C164 C 0.2721(6) 0.5660(3) 0.2695(4) 0.036(2) Uani 1 1 d . . .
H16G H 0.3145 0.5391 0.3042 0.043 Uiso 1 1 calc R . .
H16H H 0.3244 0.5939 0.2601 0.043 Uiso 1 1 calc R . .
C165 C 0.1124(6) 0.6262(3) 0.2451(4) 0.038(2) Uani 1 1 d . . .
H16J H 0.1576 0.6527 0.2257 0.045 Uiso 1 1 calc R . .
H16I H 0.0596 0.6469 0.2661 0.045 Uiso 1 1 calc R . .
C166 C 0.0494(6) 0.5902(3) 0.1851(4) 0.034(2) Uani 1 1 d . . .
H16K H -0.0296 0.5890 0.1864 0.041 Uiso 1 1 calc R . .
H16L H 0.0538 0.6058 0.1382 0.041 Uiso 1 1 calc R . .
N171 N 0.6730(5) 0.5985(2) 0.6460(3) 0.0264(15) Uani 1 1 d . . .
H17M H 0.7074 0.6192 0.6859 0.040 Uiso 1 1 calc R . .
N172 N 0.5783(5) 0.5423(3) 0.5384(3) 0.0341(17) Uani 1 1 d . . .
H17N H 0.5432 0.5216 0.4986 0.051 Uiso 1 1 calc R . .
C171 C 0.6077(6) 0.5530(3) 0.6680(4) 0.0372(19) Uani 1 1 d . . .
H17B H 0.5462 0.5684 0.6863 0.045 Uiso 1 1 calc R . .
H17A H 0.6559 0.5315 0.7072 0.045 Uiso 1 1 calc R . .
C172 C 0.5612(6) 0.5158(3) 0.6036(4) 0.036(2) Uani 1 1 d . . .
H17C H 0.5993 0.4800 0.6106 0.044 Uiso 1 1 calc R . .
H17D H 0.4812 0.5095 0.5989 0.044 Uiso 1 1 calc R . .
C173 C 0.6988(5) 0.5443(3) 0.5416(4) 0.0382(19) Uani 1 1 d . . .
H17F H 0.7117 0.5644 0.4996 0.046 Uiso 1 1 calc R . .
H17E H 0.7284 0.5068 0.5410 0.046 Uiso 1 1 calc R . .
C174 C 0.7576(6) 0.5737(3) 0.6121(4) 0.038(2) Uani 1 1 d . . .
H17G H 0.8033 0.5472 0.6457 0.045 Uiso 1 1 calc R . .
H17H H 0.8070 0.6026 0.6015 0.045 Uiso 1 1 calc R . .
C175 C 0.5972(6) 0.6329(3) 0.5929(4) 0.0325(19) Uani 1 1 d . . .
H17J H 0.6398 0.6611 0.5741 0.039 Uiso 1 1 calc R . .
H17I H 0.5444 0.6516 0.6161 0.039 Uiso 1 1 calc R . .
C176 C 0.5332(6) 0.5965(3) 0.5304(4) 0.039(2) Uani 1 1 d . . .
H17K H 0.4539 0.5953 0.5307 0.047 Uiso 1 1 calc R . .
H17L H 0.5394 0.6121 0.4838 0.047 Uiso 1 1 calc R . .
N181 N 0.1688(5) 0.6031(2) 0.6298(3) 0.0259(15) Uani 1 1 d . . .
H18M H 0.2030 0.6240 0.6696 0.039 Uiso 1 1 calc R . .
N182 N 0.0735(5) 0.5470(3) 0.5217(3) 0.0330(17) Uani 1 1 d . . .
H18N H 0.0376 0.5264 0.4820 0.049 Uiso 1 1 calc R . .
C181 C 0.0482(6) 0.6002(3) 0.6239(4) 0.039(2) Uani 1 1 d . . .
H18B H 0.0170 0.6375 0.6228 0.047 Uiso 1 1 calc R . .
H18A H 0.0339 0.5806 0.6660 0.047 Uiso 1 1 calc R . .
C182 C -0.0061(6) 0.5699(3) 0.5550(4) 0.037(2) Uani 1 1 d . . .
H18C H -0.0537 0.5404 0.5662 0.045 Uiso 1 1 calc R . .
H18D H -0.0539 0.5955 0.5211 0.045 Uiso 1 1 calc R . .
C183 C 0.1409(6) 0.5905(3) 0.4979(4) 0.038(2) Uani 1 1 d . . .
H18F H 0.0945 0.6117 0.4576 0.046 Uiso 1 1 calc R . .
H18E H 0.2028 0.5739 0.4813 0.046 Uiso 1 1 calc R . .
C184 C 0.1864(7) 0.6286(3) 0.5633(4) 0.039(2) Uani 1 1 d . . .
H18G H 0.2664 0.6350 0.5684 0.047 Uiso 1 1 calc R . .
H18H H 0.1480 0.6643 0.5553 0.047 Uiso 1 1 calc R . .
C185 C 0.2157(6) 0.5467(3) 0.6366(4) 0.039(2) Uani 1 1 d . . .
H18I H 0.2127 0.5309 0.6837 0.047 Uiso 1 1 calc R . .
H18J H 0.2942 0.5479 0.6341 0.047 Uiso 1 1 calc R . .
C186 C 0.1480(6) 0.5106(3) 0.5748(4) 0.041(2) Uani 1 1 d . . .
H18L H 0.1985 0.4905 0.5512 0.049 Uiso 1 1 calc R . .
H18K H 0.1035 0.4836 0.5942 0.049 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O11 C17 1.219(9) . ?
O12 C17 1.305(9) . ?
C11 C16 1.346(10) . ?
C11 C12 1.461(10) . ?
C11 C17 1.502(10) . ?
C12 C13 1.419(12) . ?
C12 H12 0.950 . ?
C13 C14 1.311(12) . ?
C13 H13 0.950 . ?
C14 C15 1.413(13) . ?
C14 H14 0.950 . ?
C15 C16 1.406(11) . ?
C15 H15 0.950 . ?
C16 H16 0.950 . ?
O21 C27 1.229(9) . ?
O22 C27 1.292(9) . ?
C21 C26 1.371(11) . ?
C21 C22 1.420(11) . ?
C21 C27 1.490(11) . ?
C22 C23 1.423(11) . ?
C22 H22 0.950 . ?
C23 C24 1.339(12) . ?
C23 H23 0.950 . ?
C24 C25 1.377(13) . ?
C24 H24 0.950 . ?
C25 C26 1.396(13) . ?
C25 H25 0.950 . ?
C26 H26 0.950 . ?
O31 C37 1.242(9) . ?
O32 C37 1.261(10) . ?
C31 C36 1.381(11) . ?
C31 C32 1.416(11) . ?
C31 C37 1.498(11) . ?
C32 C33 1.377(12) . ?
C32 H32 0.950 . ?
C33 C34 1.365(13) . ?
C33 H33 0.950 . ?
C34 C35 1.330(13) . ?
C34 H34 0.950 . ?
C35 C36 1.395(13) . ?
C35 H35 0.950 . ?
C36 H36 0.950 . ?
O41 C47 1.239(9) . ?
O42 C47 1.287(10) . ?
C41 C46 1.374(11) . ?
C41 C42 1.443(11) . ?
C41 C47 1.479(11) . ?
C42 C43 1.437(12) . ?
C42 H42 0.950 . ?
C43 C44 1.315(13) . ?
C43 H43 0.950 . ?
C44 C45 1.400(13) . ?
C44 H44 0.950 . ?
C45 C46 1.406(12) . ?
C45 H45 0.950 . ?
C46 H46 0.950 . ?
O51 C57 1.222(9) . ?
O52 C57 1.279(9) . ?
C51 C56 1.357(10) . ?
C51 C52 1.421(11) . ?
C51 C57 1.489(11) . ?
C52 C53 1.420(12) . ?
C52 H52 0.950 . ?
C53 C54 1.328(14) . ?
C53 H53 0.950 . ?
C54 C55 1.421(14) . ?
C54 H54 0.950 . ?
C55 C56 1.408(11) . ?
C55 H55 0.950 . ?
C56 H56 0.950 . ?
O61 C67 1.232(9) . ?
O62 C67 1.289(9) . ?
C61 C66 1.349(11) . ?
C61 C62 1.430(11) . ?
C61 C67 1.480(11) . ?
C62 C63 1.427(13) . ?
C62 H62 0.950 . ?
C63 C64 1.342(13) . ?
C63 H63 0.950 . ?
C64 C65 1.409(13) . ?
C64 H64 0.950 . ?
C65 C66 1.377(11) . ?
C65 H65 0.950 . ?
C66 H66 0.950 . ?
O71 C77 1.220(9) . ?
O72 C77 1.302(9) . ?
C71 C72 1.348(11) . ?
C71 C76 1.420(11) . ?
C71 C77 1.480(11) . ?
C72 C73 1.348(11) . ?
C72 H72 0.950 . ?
C73 C74 1.413(13) . ?
C73 H73 0.950 . ?
C74 C75 1.367(13) . ?
C74 H74 0.950 . ?
C75 C76 1.357(12) . ?
C75 H75 0.950 . ?
C76 H76 0.950 . ?
O81 C87 1.203(9) . ?
O82 C87 1.318(10) . ?
C81 C82 1.363(11) . ?
C81 C86 1.391(10) . ?
C81 C87 1.502(12) . ?
C82 C83 1.367(12) . ?
C82 H82A 0.950 . ?
C83 C84 1.364(12) . ?
C83 H83 0.950 . ?
C84 C85 1.395(13) . ?
C84 H84 0.950 . ?
C85 C86 1.370(11) . ?
C85 H85 0.950 . ?
C86 H86 0.950 . ?
O91 C97 1.207(9) . ?
O92 C97 1.280(9) . ?
C91 C92 1.335(11) . ?
C91 C96 1.413(11) . ?
C91 C97 1.528(12) . ?
C92 C93 1.356(11) . ?
C92 H92 0.950 . ?
C93 C94 1.392(13) . ?
C93 H93 0.950 . ?
C94 C95 1.362(13) . ?
C94 H94 0.950 . ?
C95 C96 1.366(11) . ?
C95 H95 0.950 . ?
C96 H96 0.950 . ?
O101 C107 1.239(9) . ?
O102 C107 1.288(9) . ?
C101 C102 1.346(11) . ?
C101 C106 1.422(11) . ?
C101 C107 1.472(12) . ?
C102 C103 1.361(12) . ?
C102 H102 0.950 . ?
C103 C104 1.427(13) . ?
C103 H103 0.950 . ?
C104 C105 1.346(12) . ?
C104 H104 0.950 . ?
C105 C106 1.357(11) . ?
C105 H105 0.950 . ?
C106 H106 0.950 . ?
C111 C112 1.361(12) . ?
C111 C116 1.418(10) . ?
C111 C117 1.506(11) . ?
O111 C117 1.241(9) . ?
O112 C117 1.274(9) . ?
C112 C113 1.368(14) . ?
C112 H112 0.950 . ?
C113 C114 1.416(14) . ?
C113 H113 0.950 . ?
C114 C115 1.310(12) . ?
C114 H114 0.950 . ?
C115 C116 1.380(11) . ?
C115 H115 0.950 . ?
C116 H116 0.950 . ?
O121 C127 1.199(9) . ?
O122 C127 1.321(9) . ?
C121 C122 1.346(11) . ?
C121 C126 1.428(11) . ?
C121 C127 1.511(11) . ?
C122 C123 1.367(12) . ?
C122 H122 0.950 . ?
C123 C124 1.396(14) . ?
C123 H123 0.950 . ?
C124 C125 1.342(14) . ?
C124 H124 0.950 . ?
C125 C126 1.340(12) . ?
C125 H125 0.950 . ?
C126 H126 0.950 . ?
N131 C131 1.480(8) . ?
N131 C134 1.488(8) . ?
N131 C135 1.497(9) . ?
N131 H13M 0.930 . ?
N132 C132 1.449(9) . ?
N132 C133 1.483(9) . ?
N132 C136 1.483(9) . ?
N132 H13N 0.930 . ?
C131 C132 1.517(9) . ?
C131 H13B 0.990 . ?
C131 H13A 0.990 . ?
C132 H13C 0.990 . ?
C132 H13D 0.990 . ?
C133 C134 1.549(10) . ?
C133 H13F 0.990 . ?
C133 H13E 0.990 . ?
C134 H13H 0.990 . ?
C134 H13G 0.990 . ?
C135 C136 1.552(9) . ?
C135 H13I 0.990 . ?
C135 H13J 0.990 . ?
C136 H13L 0.990 . ?
C136 H13K 0.990 . ?
N141 C141 1.466(9) . ?
N141 C145 1.477(9) . ?
N141 C144 1.498(9) . ?
N141 H14M 0.930 . ?
N142 C143 1.469(9) . ?
N142 C142 1.471(9) . ?
N142 C146 1.473(9) . ?
N142 H14N 0.930 . ?
C141 C142 1.536(9) . ?
C141 H14B 0.990 . ?
C141 H14A 0.990 . ?
C142 H14C 0.990 . ?
C142 H14D 0.990 . ?
C143 C144 1.530(10) . ?
C143 H14E 0.990 . ?
C143 H14F 0.990 . ?
C144 H14G 0.990 . ?
C144 H14H 0.990 . ?
C145 C146 1.537(9) . ?
C145 H14I 0.990 . ?
C145 H14J 0.990 . ?
C146 H14L 0.990 . ?
C146 H14K 0.990 . ?
N151 C155 1.450(9) . ?
N151 C151 1.461(9) . ?
N151 C154 1.508(9) . ?
N151 H15M 0.930 . ?
N152 C156 1.454(10) . ?
N152 C152 1.460(8) . ?
N152 C153 1.489(8) . ?
N152 H15N 0.930 . ?
C151 C152 1.534(9) . ?
C151 H15B 0.990 . ?
C151 H15A 0.990 . ?
C152 H15C 0.990 . ?
C152 H15D 0.990 . ?
C153 C154 1.525(9) . ?
C153 H15F 0.990 . ?
C153 H15E 0.990 . ?
C154 H15H 0.990 . ?
C154 H15G 0.990 . ?
C155 C156 1.539(9) . ?
C155 H15J 0.990 . ?
C155 H15I 0.990 . ?
C156 H15K 0.990 . ?
C156 H15L 0.990 . ?
N161 C165 1.463(9) . ?
N161 C161 1.477(9) . ?
N161 C164 1.523(9) . ?
N161 H16M 0.930 . ?
N162 C163 1.470(9) . ?
N162 C162 1.478(9) . ?
N162 C166 1.486(10) . ?
N162 H16N 0.930 . ?
C161 C162 1.511(10) . ?
C161 H16B 0.990 . ?
C161 H16A 0.990 . ?
C162 H16C 0.990 . ?
C162 H16D 0.990 . ?
C163 C164 1.549(10) . ?
C163 H16F 0.990 . ?
C163 H16E 0.990 . ?
C164 H16G 0.990 . ?
C164 H16H 0.990 . ?
C165 C166 1.506(10) . ?
C165 H16J 0.990 . ?
C165 H16I 0.990 . ?
C166 H16K 0.990 . ?
C166 H16L 0.990 . ?
N171 C175 1.471(8) . ?
N171 C174 1.493(8) . ?
N171 C171 1.497(9) . ?
N171 H17M 0.930 . ?
N172 C176 1.432(9) . ?
N172 C172 1.467(9) . ?
N172 C173 1.488(8) . ?
N172 H17N 0.930 . ?
C171 C172 1.529(9) . ?
C171 H17B 0.990 . ?
C171 H17A 0.990 . ?
C172 H17C 0.990 . ?
C172 H17D 0.990 . ?
C173 C174 1.547(9) . ?
C173 H17F 0.990 . ?
C173 H17E 0.990 . ?
C174 H17G 0.990 . ?
C174 H17H 0.990 . ?
C175 C176 1.548(9) . ?
C175 H17J 0.990 . ?
C175 H17I 0.990 . ?
C176 H17K 0.990 . ?
C176 H17L 0.990 . ?
N181 C184 1.480(9) . ?
N181 C181 1.480(9) . ?
N181 C185 1.492(9) . ?
N181 H18M 0.930 . ?
N182 C182 1.418(9) . ?
N182 C186 1.492(9) . ?
N182 C183 1.493(9) . ?
N182 H18N 0.930 . ?
C181 C182 1.521(9) . ?
C181 H18B 0.990 . ?
C181 H18A 0.990 . ?
C182 H18C 0.990 . ?
C182 H18D 0.990 . ?
C183 C184 1.552(10) . ?
C183 H18F 0.990 . ?
C183 H18E 0.990 . ?
C184 H18G 0.990 . ?
C184 H18H 0.990 . ?
C185 C186 1.552(10) . ?
C185 H18I 0.990 . ?
C185 H18J 0.990 . ?
C186 H18L 0.990 . ?
C186 H18K 0.990 . ?

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
C16 C11 C12 119.9(8) . . ?
C16 C11 C17 123.2(7) . . ?
C12 C11 C17 116.7(7) . . ?
C13 C12 C11 116.1(8) . . ?
C13 C12 H12 122.0 . . ?
C11 C12 H12 122.0 . . ?
C14 C13 C12 123.3(9) . . ?
C14 C13 H13 118.3 . . ?
C12 C13 H13 118.3 . . ?
C13 C14 C15 120.3(10) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C16 C15 C14 119.1(9) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C11 C16 C15 121.2(9) . . ?
C11 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
O11 C17 O12 125.3(7) . . ?
O11 C17 C11 121.5(8) . . ?
O12 C17 C11 113.2(7) . . ?
C26 C21 C22 118.2(7) . . ?
C26 C21 C27 121.5(8) . . ?
C22 C21 C27 119.7(8) . . ?
C21 C22 C23 118.7(8) . . ?
C21 C22 H22 120.6 . . ?
C23 C22 H22 120.6 . . ?
C24 C23 C22 120.4(9) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C25 121.5(10) . . ?
C23 C24 H24 119.2 . . ?
C25 C24 H24 119.2 . . ?
C24 C25 C26 119.0(9) . . ?
C24 C25 H25 120.5 . . ?
C26 C25 H25 120.5 . . ?
C21 C26 C25 121.8(9) . . ?
C21 C26 H26 119.1 . . ?
C25 C26 H26 119.1 . . ?
O21 C27 O22 123.3(8) . . ?
O21 C27 C21 120.6(8) . . ?
O22 C27 C21 116.0(8) . . ?
C36 C31 C32 118.3(8) . . ?
C36 C31 C37 121.8(9) . . ?
C32 C31 C37 119.8(8) . . ?
C33 C32 C31 119.7(9) . . ?
C33 C32 H32 120.1 . . ?
C31 C32 H32 120.1 . . ?
C34 C33 C32 120.4(10) . . ?
C34 C33 H33 119.8 . . ?
C32 C33 H33 119.8 . . ?
C35 C34 C33 120.2(10) . . ?
C35 C34 H34 119.9 . . ?
C33 C34 H34 119.9 . . ?
C34 C35 C36 121.9(10) . . ?
C34 C35 H35 119.0 . . ?
C36 C35 H35 119.0 . . ?
C31 C36 C35 119.2(9) . . ?
C31 C36 H36 120.4 . . ?
C35 C36 H36 120.4 . . ?
O31 C37 O32 125.2(8) . . ?
O31 C37 C31 118.4(9) . . ?
O32 C37 C31 116.4(8) . . ?
C46 C41 C42 119.7(8) . . ?
C46 C41 C47 123.1(9) . . ?
C42 C41 C47 116.8(9) . . ?
C43 C42 C41 115.6(9) . . ?
C43 C42 H42 122.2 . . ?
C41 C42 H42 122.2 . . ?
C44 C43 C42 122.9(10) . . ?
C44 C43 H43 118.6 . . ?
C42 C43 H43 118.6 . . ?
C43 C44 C45 122.1(10) . . ?
C43 C44 H44 119.0 . . ?
C45 C44 H44 119.0 . . ?
C44 C45 C46 117.3(9) . . ?
C44 C45 H45 121.3 . . ?
C46 C45 H45 121.3 . . ?
C41 C46 C45 122.2(9) . . ?
C41 C46 H46 118.9 . . ?
C45 C46 H46 118.9 . . ?
O41 C47 O42 124.1(8) . . ?
O41 C47 C41 121.5(9) . . ?
O42 C47 C41 114.4(8) . . ?
C56 C51 C52 117.8(8) . . ?
C56 C51 C57 123.8(8) . . ?
C52 C51 C57 117.9(8) . . ?
C53 C52 C51 118.6(9) . . ?
C53 C52 H52 120.7 . . ?
C51 C52 H52 120.7 . . ?
C54 C53 C52 121.6(10) . . ?
C54 C53 H53 119.2 . . ?
C52 C53 H53 119.2 . . ?
C53 C54 C55 121.2(10) . . ?
C53 C54 H54 119.4 . . ?
C55 C54 H54 119.4 . . ?
C56 C55 C54 116.5(9) . . ?
C56 C55 H55 121.8 . . ?
C54 C55 H55 121.8 . . ?
C51 C56 C55 123.9(9) . . ?
C51 C56 H56 118.1 . . ?
C55 C56 H56 118.1 . . ?
O51 C57 O52 126.1(8) . . ?
O51 C57 C51 119.9(8) . . ?
O52 C57 C51 114.0(8) . . ?
C66 C61 C62 119.7(8) . . ?
C66 C61 C67 123.3(8) . . ?
C62 C61 C67 116.8(8) . . ?
C63 C62 C61 116.9(8) . . ?
C63 C62 H62 121.5 . . ?
C61 C62 H62 121.5 . . ?
C64 C63 C62 121.8(9) . . ?
C64 C63 H63 119.1 . . ?
C62 C63 H63 119.1 . . ?
C63 C64 C65 120.0(9) . . ?
C63 C64 H64 120.0 . . ?
C65 C64 H64 120.0 . . ?
C66 C65 C64 119.0(9) . . ?
C66 C65 H65 120.5 . . ?
C64 C65 H65 120.5 . . ?
C61 C66 C65 122.5(9) . . ?
C61 C66 H66 118.8 . . ?
C65 C66 H66 118.8 . . ?
O61 C67 O62 124.5(8) . . ?
O61 C67 C61 122.2(8) . . ?
O62 C67 C61 113.3(7) . . ?
C72 C71 C76 116.6(8) . . ?
C72 C71 C77 124.1(8) . . ?
C76 C71 C77 119.3(7) . . ?
C71 C72 C73 126.4(9) . . ?
C71 C72 H72 116.8 . . ?
C73 C72 H72 116.8 . . ?
C72 C73 C74 115.6(9) . . ?
C72 C73 H73 122.2 . . ?
C74 C73 H73 122.2 . . ?
C75 C74 C73 120.5(9) . . ?
C75 C74 H74 119.8 . . ?
C73 C74 H74 119.8 . . ?
C76 C75 C74 121.4(9) . . ?
C76 C75 H75 119.3 . . ?
C74 C75 H75 119.3 . . ?
C75 C76 C71 119.4(9) . . ?
C75 C76 H76 120.3 . . ?
C71 C76 H76 120.3 . . ?
O71 C77 O72 122.7(8) . . ?
O71 C77 C71 119.8(7) . . ?
O72 C77 C71 117.4(8) . . ?
C82 C81 C86 120.5(8) . . ?
C82 C81 C87 121.0(8) . . ?
C86 C81 C87 118.5(8) . . ?
C81 C82 C83 120.0(9) . . ?
C81 C82 H82A 120.0 . . ?
C83 C82 H82A 120.0 . . ?
C84 C83 C82 120.2(10) . . ?
C84 C83 H83 119.9 . . ?
C82 C83 H83 119.9 . . ?
C83 C84 C85 120.4(9) . . ?
C83 C84 H84 119.8 . . ?
C85 C84 H84 119.8 . . ?
C86 C85 C84 119.2(9) . . ?
C86 C85 H85 120.4 . . ?
C84 C85 H85 120.4 . . ?
C85 C86 C81 119.6(9) . . ?
C85 C86 H86 120.2 . . ?
C81 C86 H86 120.2 . . ?
O81 C87 O82 123.8(8) . . ?
O81 C87 C81 122.9(8) . . ?
O82 C87 C81 113.3(7) . . ?
C92 C91 C96 119.3(8) . . ?
C92 C91 C97 121.9(8) . . ?
C96 C91 C97 118.7(8) . . ?
C91 C92 C93 122.5(9) . . ?
C91 C92 H92 118.7 . . ?
C93 C92 H92 118.7 . . ?
C92 C93 C94 117.9(9) . . ?
C92 C93 H93 121.0 . . ?
C94 C93 H93 121.0 . . ?
C95 C94 C93 121.1(9) . . ?
C95 C94 H94 119.5 . . ?
C93 C94 H94 119.4 . . ?
C94 C95 C96 119.8(8) . . ?
C94 C95 H95 120.1 . . ?
C96 C95 H95 120.1 . . ?
C95 C96 C91 119.1(8) . . ?
C95 C96 H96 120.5 . . ?
C91 C96 H96 120.5 . . ?
O91 C97 O92 125.1(8) . . ?
O91 C97 C91 120.9(8) . . ?
O92 C97 C91 113.9(8) . . ?
C102 C101 C106 116.4(8) . . ?
C102 C101 C107 124.1(8) . . ?
C106 C101 C107 119.5(8) . . ?
C101 C102 C103 125.1(9) . . ?
C101 C102 H102 117.5 . . ?
C103 C102 H102 117.5 . . ?
C102 C103 C104 115.8(9) . . ?
C102 C103 H103 122.1 . . ?
C104 C103 H103 122.1 . . ?
C105 C104 C103 121.6(9) . . ?
C105 C104 H104 119.2 . . ?
C103 C104 H104 119.2 . . ?
C104 C105 C106 119.7(9) . . ?
C104 C105 H105 120.1 . . ?
C106 C105 H105 120.1 . . ?
C105 C106 C101 121.2(8) . . ?
C105 C106 H106 119.4 . . ?
C101 C106 H106 119.4 . . ?
O101 C107 O102 121.2(8) . . ?
O101 C107 C101 119.0(8) . . ?
O102 C107 C101 119.8(8) . . ?
C112 C111 C116 117.9(9) . . ?
C112 C111 C117 123.0(8) . . ?
C116 C111 C117 119.1(8) . . ?
C111 C112 C113 122.2(10) . . ?
C111 C112 H112 118.9 . . ?
C113 C112 H112 118.9 . . ?
C112 C113 C114 117.9(10) . . ?
C112 C113 H113 121.1 . . ?
C114 C113 H113 121.1 . . ?
C115 C114 C113 121.4(10) . . ?
C115 C114 H114 119.3 . . ?
C113 C114 H114 119.3 . . ?
C114 C115 C116 120.9(9) . . ?
C114 C115 H115 119.6 . . ?
C116 C115 H115 119.6 . . ?
C115 C116 C111 119.7(8) . . ?
C115 C116 H116 120.2 . . ?
C111 C116 H116 120.2 . . ?
O111 C117 O112 123.4(8) . . ?
O111 C117 C111 118.3(8) . . ?
O112 C117 C111 118.2(8) . . ?
C122 C121 C126 118.8(8) . . ?
C122 C121 C127 121.7(8) . . ?
C126 C121 C127 119.3(8) . . ?
C121 C122 C123 123.0(9) . . ?
C121 C122 H122 118.5 . . ?
C123 C122 H122 118.5 . . ?
C122 C123 C124 117.5(10) . . ?
C122 C123 H123 121.3 . . ?
C124 C123 H123 121.3 . . ?
C125 C124 C123 119.0(10) . . ?
C125 C124 H124 120.5 . . ?
C123 C124 H124 120.5 . . ?
C126 C125 C124 124.8(11) . . ?
C126 C125 H125 117.6 . . ?
C124 C125 H125 117.6 . . ?
C125 C126 C121 116.6(9) . . ?
C125 C126 H126 121.7 . . ?
C121 C126 H126 121.7 . . ?
O121 C127 O122 122.9(8) . . ?
O121 C127 C121 120.9(8) . . ?
O122 C127 C121 116.2(7) . . ?
C131 N131 C134 109.2(6) . . ?
C131 N131 C135 109.4(6) . . ?
C134 N131 C135 109.4(6) . . ?
C131 N131 H13M 109.6 . . ?
C134 N131 H13M 109.6 . . ?
C135 N131 H13M 109.6 . . ?
C132 N132 C133 109.3(6) . . ?
C132 N132 C136 109.6(6) . . ?
C133 N132 C136 109.0(6) . . ?
C132 N132 H13N 109.6 . . ?
C133 N132 H13N 109.6 . . ?
C136 N132 H13N 109.6 . . ?
N131 C131 C132 109.0(5) . . ?
N131 C131 H13B 109.9 . . ?
C132 C131 H13B 109.9 . . ?
N131 C131 H13A 109.9 . . ?
C132 C131 H13A 109.9 . . ?
H13B C131 H13A 108.3 . . ?
N132 C132 C131 110.6(6) . . ?
N132 C132 H13C 109.5 . . ?
C131 C132 H13C 109.5 . . ?
N132 C132 H13D 109.5 . . ?
C131 C132 H13D 109.5 . . ?
H13C C132 H13D 108.1 . . ?
N132 C133 C134 109.6(5) . . ?
N132 C133 H13F 109.8 . . ?
C134 C133 H13F 109.8 . . ?
N132 C133 H13E 109.8 . . ?
C134 C133 H13E 109.8 . . ?
H13F C133 H13E 108.2 . . ?
N131 C134 C133 108.1(6) . . ?
N131 C134 H13H 110.1 . . ?
C133 C134 H13H 110.1 . . ?
N131 C134 H13G 110.1 . . ?
C133 C134 H13G 110.1 . . ?
H13H C134 H13G 108.4 . . ?
N131 C135 C136 108.4(5) . . ?
N131 C135 H13I 110.0 . . ?
C136 C135 H13I 110.0 . . ?
N131 C135 H13J 110.0 . . ?
C136 C135 H13J 110.0 . . ?
H13I C135 H13J 108.4 . . ?
N132 C136 C135 109.0(6) . . ?
N132 C136 H13L 109.9 . . ?
C135 C136 H13L 109.9 . . ?
N132 C136 H13K 109.9 . . ?
C135 C136 H13K 109.9 . . ?
H13L C136 H13K 108.3 . . ?
C141 N141 C145 109.3(6) . . ?
C141 N141 C144 109.9(6) . . ?
C145 N141 C144 107.8(6) . . ?
C141 N141 H14M 109.9 . . ?
C145 N141 H14M 109.9 . . ?
C144 N141 H14M 109.9 . . ?
C143 N142 C142 109.3(6) . . ?
C143 N142 C146 109.4(6) . . ?
C142 N142 C146 111.2(6) . . ?
C143 N142 H14N 109.0 . . ?
C142 N142 H14N 109.0 . . ?
C146 N142 H14N 109.0 . . ?
N141 C141 C142 110.2(6) . . ?
N141 C141 H14B 109.6 . . ?
C142 C141 H14B 109.6 . . ?
N141 C141 H14A 109.6 . . ?
C142 C141 H14A 109.6 . . ?
H14B C141 H14A 108.1 . . ?
N142 C142 C141 108.9(6) . . ?
N142 C142 H14C 109.9 . . ?
C141 C142 H14C 109.9 . . ?
N142 C142 H14D 109.9 . . ?
C141 C142 H14D 109.9 . . ?
H14C C142 H14D 108.3 . . ?
N142 C143 C144 109.5(6) . . ?
N142 C143 H14E 109.8 . . ?
C144 C143 H14E 109.8 . . ?
N142 C143 H14F 109.8 . . ?
C144 C143 H14F 109.8 . . ?
H14E C143 H14F 108.2 . . ?
N141 C144 C143 109.3(6) . . ?
N141 C144 H14G 109.8 . . ?
C143 C144 H14G 109.8 . . ?
N141 C144 H14H 109.8 . . ?
C143 C144 H14H 109.8 . . ?
H14G C144 H14H 108.3 . . ?
N141 C145 C146 110.3(5) . . ?
N141 C145 H14I 109.6 . . ?
C146 C145 H14I 109.6 . . ?
N141 C145 H14J 109.6 . . ?
C146 C145 H14J 109.6 . . ?
H14I C145 H14J 108.1 . . ?
N142 C146 C145 108.4(6) . . ?
N142 C146 H14L 110.0 . . ?
C145 C146 H14L 110.0 . . ?
N142 C146 H14K 110.0 . . ?
C145 C146 H14K 110.0 . . ?
H14L C146 H14K 108.4 . . ?
C155 N151 C151 110.7(6) . . ?
C155 N151 C154 107.7(6) . . ?
C151 N151 C154 108.7(6) . . ?
C155 N151 H15M 109.9 . . ?
C151 N151 H15M 109.9 . . ?
C154 N151 H15M 109.9 . . ?
C156 N152 C152 111.2(6) . . ?
C156 N152 C153 108.2(6) . . ?
C152 N152 C153 108.1(6) . . ?
C156 N152 H15N 109.8 . . ?
C152 N152 H15N 109.8 . . ?
C153 N152 H15N 109.8 . . ?
N151 C151 C152 109.2(6) . . ?
N151 C151 H15B 109.8 . . ?
C152 C151 H15B 109.8 . . ?
N151 C151 H15A 109.8 . . ?
C152 C151 H15A 109.8 . . ?
H15B C151 H15A 108.3 . . ?
N152 C152 C151 110.6(6) . . ?
N152 C152 H15C 109.5 . . ?
C151 C152 H15C 109.5 . . ?
N152 C152 H15D 109.5 . . ?
C151 C152 H15D 109.5 . . ?
H15C C152 H15D 108.1 . . ?
N152 C153 C154 109.2(6) . . ?
N152 C153 H15F 109.8 . . ?
C154 C153 H15F 109.8 . . ?
N152 C153 H15E 109.8 . . ?
C154 C153 H15E 109.8 . . ?
H15F C153 H15E 108.3 . . ?
N151 C154 C153 109.8(5) . . ?
N151 C154 H15H 109.7 . . ?
C153 C154 H15H 109.7 . . ?
N151 C154 H15G 109.7 . . ?
C153 C154 H15G 109.7 . . ?
H15H C154 H15G 108.2 . . ?
N151 C155 C156 110.0(6) . . ?
N151 C155 H15J 109.7 . . ?
C156 C155 H15J 109.7 . . ?
N151 C155 H15I 109.7 . . ?
C156 C155 H15I 109.7 . . ?
H15J C155 H15I 108.2 . . ?
N152 C156 C155 109.6(5) . . ?
N152 C156 H15K 109.7 . . ?
C155 C156 H15K 109.7 . . ?
N152 C156 H15L 109.7 . . ?
C155 C156 H15L 109.7 . . ?
H15K C156 H15L 108.2 . . ?
C165 N161 C161 109.0(6) . . ?
C165 N161 C164 108.7(6) . . ?
C161 N161 C164 106.7(6) . . ?
C165 N161 H16M 110.8 . . ?
C161 N161 H16M 110.8 . . ?
C164 N161 H16M 110.8 . . ?
C163 N162 C162 108.3(6) . . ?
C163 N162 C166 109.3(6) . . ?
C162 N162 C166 107.9(6) . . ?
C163 N162 H16N 110.4 . . ?
C162 N162 H16N 110.4 . . ?
C166 N162 H16N 110.4 . . ?
N161 C161 C162 109.9(6) . . ?
N161 C161 H16B 109.7 . . ?
C162 C161 H16B 109.7 . . ?
N161 C161 H16A 109.7 . . ?
C162 C161 H16A 109.7 . . ?
H16B C161 H16A 108.2 . . ?
N162 C162 C161 110.9(6) . . ?
N162 C162 H16C 109.5 . . ?
C161 C162 H16C 109.5 . . ?
N162 C162 H16D 109.5 . . ?
C161 C162 H16D 109.5 . . ?
H16C C162 H16D 108.0 . . ?
N162 C163 C164 109.0(6) . . ?
N162 C163 H16F 109.9 . . ?
C164 C163 H16F 109.9 . . ?
N162 C163 H16E 109.9 . . ?
C164 C163 H16E 109.9 . . ?
H16F C163 H16E 108.3 . . ?
N161 C164 C163 109.6(6) . . ?
N161 C164 H16G 109.7 . . ?
C163 C164 H16G 109.7 . . ?
N161 C164 H16H 109.7 . . ?
C163 C164 H16H 109.7 . . ?
H16G C164 H16H 108.2 . . ?
N161 C165 C166 110.5(6) . . ?
N161 C165 H16J 109.5 . . ?
C166 C165 H16J 109.5 . . ?
N161 C165 H16I 109.5 . . ?
C166 C165 H16I 109.5 . . ?
H16J C165 H16I 108.1 . . ?
N162 C166 C165 110.5(6) . . ?
N162 C166 H16K 109.5 . . ?
C165 C166 H16K 109.5 . . ?
N162 C166 H16L 109.5 . . ?
C165 C166 H16L 109.5 . . ?
H16K C166 H16L 108.1 . . ?
C175 N171 C174 109.5(5) . . ?
C175 N171 C171 108.5(5) . . ?
C174 N171 C171 108.1(6) . . ?
C175 N171 H17M 110.2 . . ?
C174 N171 H17M 110.2 . . ?
C171 N171 H17M 110.2 . . ?
C176 N172 C172 111.4(6) . . ?
C176 N172 C173 109.8(6) . . ?
C172 N172 C173 109.4(6) . . ?
C176 N172 H17N 108.7 . . ?
C172 N172 H17N 108.7 . . ?
C173 N172 H17N 108.7 . . ?
N171 C171 C172 109.9(5) . . ?
N171 C171 H17B 109.7 . . ?
C172 C171 H17B 109.7 . . ?
N171 C171 H17A 109.7 . . ?
C172 C171 H17A 109.7 . . ?
H17B C171 H17A 108.2 . . ?
N172 C172 C171 108.6(6) . . ?
N172 C172 H17C 110.0 . . ?
C171 C172 H17C 110.0 . . ?
N172 C172 H17D 110.0 . . ?
C171 C172 H17D 110.0 . . ?
H17C C172 H17D 108.3 . . ?
N172 C173 C174 108.1(5) . . ?
N172 C173 H17F 110.1 . . ?
C174 C173 H17F 110.1 . . ?
N172 C173 H17E 110.1 . . ?
C174 C173 H17E 110.1 . . ?
H17F C173 H17E 108.4 . . ?
N171 C174 C173 109.5(5) . . ?
N171 C174 H17G 109.8 . . ?
C173 C174 H17G 109.8 . . ?
N171 C174 H17H 109.8 . . ?
C173 C174 H17H 109.8 . . ?
H17G C174 H17H 108.2 . . ?
N171 C175 C176 109.2(6) . . ?
N171 C175 H17J 109.8 . . ?
C176 C175 H17J 109.8 . . ?
N171 C175 H17I 109.8 . . ?
C176 C175 H17I 109.8 . . ?
H17J C175 H17I 108.3 . . ?
N172 C176 C175 109.5(5) . . ?
N172 C176 H17K 109.8 . . ?
C175 C176 H17K 109.8 . . ?
N172 C176 H17L 109.8 . . ?
C175 C176 H17L 109.8 . . ?
H17K C176 H17L 108.2 . . ?
C184 N181 C181 108.3(6) . . ?
C184 N181 C185 109.1(6) . . ?
C181 N181 C185 109.3(6) . . ?
C184 N181 H18M 110.0 . . ?
C181 N181 H18M 110.0 . . ?
C185 N181 H18M 110.0 . . ?
C182 N182 C186 108.4(6) . . ?
C182 N182 C183 111.2(6) . . ?
C186 N182 C183 109.3(6) . . ?
C182 N182 H18N 109.3 . . ?
C186 N182 H18N 109.3 . . ?
C183 N182 H18N 109.3 . . ?
N181 C181 C182 108.6(6) . . ?
N181 C181 H18B 110.0 . . ?
C182 C181 H18B 110.0 . . ?
N181 C181 H18A 110.0 . . ?
C182 C181 H18A 110.0 . . ?
H18B C181 H18A 108.4 . . ?
N182 C182 C181 111.7(6) . . ?
N182 C182 H18C 109.3 . . ?
C181 C182 H18C 109.3 . . ?
N182 C182 H18D 109.3 . . ?
C181 C182 H18D 109.3 . . ?
H18C C182 H18D 107.9 . . ?
N182 C183 C184 107.6(6) . . ?
N182 C183 H18F 110.2 . . ?
C184 C183 H18F 110.2 . . ?
N182 C183 H18E 110.2 . . ?
C184 C183 H18E 110.2 . . ?
H18F C183 H18E 108.5 . . ?
N181 C184 C183 110.0(6) . . ?
N181 C184 H18G 109.7 . . ?
C183 C184 H18G 109.7 . . ?
N181 C184 H18H 109.7 . . ?
C183 C184 H18H 109.7 . . ?
H18G C184 H18H 108.2 . . ?
N181 C185 C186 109.3(6) . . ?
N181 C185 H18I 109.8 . . ?
C186 C185 H18I 109.8 . . ?
N181 C185 H18J 109.8 . . ?
C186 C185 H18J 109.8 . . ?
H18I C185 H18J 108.3 . . ?
N182 C186 C185 108.3(6) . . ?
N182 C186 H18L 110.0 . . ?
C185 C186 H18L 110.0 . . ?
N182 C186 H18K 110.0 . . ?
C185 C186 H18K 110.0 . . ?
H18L C186 H18K 108.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 C11 C12 C13 -4.2(12) . . . . ?
C17 C11 C12 C13 -179.6(7) . . . . ?
C11 C12 C13 C14 1.2(13) . . . . ?
C12 C13 C14 C15 1.7(15) . . . . ?
C13 C14 C15 C16 -1.9(15) . . . . ?
C12 C11 C16 C15 4.1(13) . . . . ?
C17 C11 C16 C15 179.2(8) . . . . ?
C14 C15 C16 C11 -1.1(14) . . . . ?
C16 C11 C17 O11 -177.3(8) . . . . ?
C12 C11 C17 O11 -2.1(11) . . . . ?
C16 C11 C17 O12 3.7(11) . . . . ?
C12 C11 C17 O12 178.9(7) . . . . ?
C26 C21 C22 C23 -6.7(12) . . . . ?
C27 C21 C22 C23 -178.2(7) . . . . ?
C21 C22 C23 C24 5.5(13) . . . . ?
C22 C23 C24 C25 -1.8(14) . . . . ?
C23 C24 C25 C26 -0.5(14) . . . . ?
C22 C21 C26 C25 4.6(12) . . . . ?
C27 C21 C26 C25 176.0(8) . . . . ?
C24 C25 C26 C21 -1.0(14) . . . . ?
C26 C21 C27 O21 1.8(12) . . . . ?
C22 C21 C27 O21 173.0(7) . . . . ?
C26 C21 C27 O22 177.5(7) . . . . ?
C22 C21 C27 O22 -11.3(10) . . . . ?
C36 C31 C32 C33 -4.5(12) . . . . ?
C37 C31 C32 C33 179.1(8) . . . . ?
C31 C32 C33 C34 5.1(14) . . . . ?
C32 C33 C34 C35 -4.1(15) . . . . ?
C33 C34 C35 C36 2.4(16) . . . . ?
C32 C31 C36 C35 2.8(12) . . . . ?
C37 C31 C36 C35 179.2(8) . . . . ?
C34 C35 C36 C31 -1.9(15) . . . . ?
C36 C31 C37 O31 6.6(12) . . . . ?
C32 C31 C37 O31 -177.2(8) . . . . ?
C36 C31 C37 O32 -172.6(8) . . . . ?
C32 C31 C37 O32 3.7(11) . . . . ?
C46 C41 C42 C43 -5.7(11) . . . . ?
C47 C41 C42 C43 -178.8(7) . . . . ?
C41 C42 C43 C44 2.8(13) . . . . ?
C42 C43 C44 C45 1.8(15) . . . . ?
C43 C44 C45 C46 -3.5(16) . . . . ?
C42 C41 C46 C45 4.2(13) . . . . ?
C47 C41 C46 C45 176.8(8) . . . . ?
C44 C45 C46 C41 0.4(14) . . . . ?
C46 C41 C47 O41 -178.1(8) . . . . ?
C42 C41 C47 O41 -5.2(11) . . . . ?
C46 C41 C47 O42 0.2(12) . . . . ?
C42 C41 C47 O42 173.0(7) . . . . ?
C56 C51 C52 C53 -8.3(12) . . . . ?
C57 C51 C52 C53 179.5(8) . . . . ?
C51 C52 C53 C54 7.4(14) . . . . ?
C52 C53 C54 C55 -2.5(17) . . . . ?
C53 C54 C55 C56 -1.3(16) . . . . ?
C52 C51 C56 C55 4.8(12) . . . . ?
C57 C51 C56 C55 176.5(8) . . . . ?
C54 C55 C56 C51 0.1(14) . . . . ?
C56 C51 C57 O51 168.5(8) . . . . ?
C52 C51 C57 O51 -19.8(11) . . . . ?
C56 C51 C57 O52 -9.2(12) . . . . ?
C52 C51 C57 O52 162.6(7) . . . . ?
C66 C61 C62 C63 -4.2(12) . . . . ?
C67 C61 C62 C63 -179.3(7) . . . . ?
C61 C62 C63 C64 1.4(13) . . . . ?
C62 C63 C64 C65 2.6(15) . . . . ?
C63 C64 C65 C66 -3.9(15) . . . . ?
C62 C61 C66 C65 3.0(13) . . . . ?
C67 C61 C66 C65 177.8(8) . . . . ?
C64 C65 C66 C61 1.1(14) . . . . ?
C66 C61 C67 O61 -164.3(8) . . . . ?
C62 C61 C67 O61 10.5(12) . . . . ?
C66 C61 C67 O62 14.4(12) . . . . ?
C62 C61 C67 O62 -170.7(7) . . . . ?
C76 C71 C72 C73 -2.1(13) . . . . ?
C77 C71 C72 C73 176.2(8) . . . . ?
C71 C72 C73 C74 2.3(13) . . . . ?
C72 C73 C74 C75 0.6(13) . . . . ?
C73 C74 C75 C76 -3.6(14) . . . . ?
C74 C75 C76 C71 3.7(13) . . . . ?
C72 C71 C76 C75 -0.9(12) . . . . ?
C77 C71 C76 C75 -179.4(8) . . . . ?
C72 C71 C77 O71 2.6(13) . . . . ?
C76 C71 C77 O71 -179.1(8) . . . . ?
C72 C71 C77 O72 -177.1(8) . . . . ?
C76 C71 C77 O72 1.3(11) . . . . ?
C86 C81 C82 C83 -2.6(12) . . . . ?
C87 C81 C82 C83 178.8(8) . . . . ?
C81 C82 C83 C84 2.7(13) . . . . ?
C82 C83 C84 C85 -0.8(14) . . . . ?
C83 C84 C85 C86 -1.2(13) . . . . ?
C84 C85 C86 C81 1.2(12) . . . . ?
C82 C81 C86 C85 0.6(12) . . . . ?
C87 C81 C86 C85 179.3(7) . . . . ?
C82 C81 C87 O81 177.9(8) . . . . ?
C86 C81 C87 O81 -0.7(12) . . . . ?
C82 C81 C87 O82 -5.0(11) . . . . ?
C86 C81 C87 O82 176.3(7) . . . . ?
C96 C91 C92 C93 -6.3(12) . . . . ?
C97 C91 C92 C93 178.0(8) . . . . ?
C91 C92 C93 C94 5.4(13) . . . . ?
C92 C93 C94 C95 -2.4(14) . . . . ?
C93 C94 C95 C96 0.5(13) . . . . ?
C94 C95 C96 C91 -1.3(12) . . . . ?
C92 C91 C96 C95 4.1(11) . . . . ?
C97 C91 C96 C95 -180.0(7) . . . . ?
C92 C91 C97 O91 -173.6(8) . . . . ?
C96 C91 C97 O91 10.6(11) . . . . ?
C92 C91 C97 O92 2.7(11) . . . . ?
C96 C91 C97 O92 -173.1(7) . . . . ?
C106 C101 C102 C103 -5.2(13) . . . . ?
C107 C101 C102 C103 177.3(8) . . . . ?
C101 C102 C103 C104 4.3(14) . . . . ?
C102 C103 C104 C105 0.1(13) . . . . ?
C103 C104 C105 C106 -3.3(13) . . . . ?
C104 C105 C106 C101 2.4(13) . . . . ?
C102 C101 C106 C105 1.6(12) . . . . ?
C107 C101 C106 C105 179.3(7) . . . . ?
C102 C101 C107 O101 -5.6(13) . . . . ?
C106 C101 C107 O101 177.0(7) . . . . ?
C102 C101 C107 O102 173.9(8) . . . . ?
C106 C101 C107 O102 -3.6(12) . . . . ?
C116 C111 C112 C113 -4.3(13) . . . . ?
C117 C111 C112 C113 177.7(8) . . . . ?
C111 C112 C113 C114 2.1(15) . . . . ?
C112 C113 C114 C115 1.4(16) . . . . ?
C113 C114 C115 C116 -2.4(15) . . . . ?
C114 C115 C116 C111 0.0(13) . . . . ?
C112 C111 C116 C115 3.2(11) . . . . ?
C117 C111 C116 C115 -178.6(7) . . . . ?
C112 C111 C117 O111 -15.7(12) . . . . ?
C116 C111 C117 O111 166.3(7) . . . . ?
C112 C111 C117 O112 161.9(8) . . . . ?
C116 C111 C117 O112 -16.1(11) . . . . ?
C126 C121 C122 C123 -6.5(13) . . . . ?
C127 C121 C122 C123 177.5(8) . . . . ?
C121 C122 C123 C124 6.5(13) . . . . ?
C122 C123 C124 C125 -2.1(14) . . . . ?
C123 C124 C125 C126 -2.2(16) . . . . ?
C124 C125 C126 C121 2.2(14) . . . . ?
C122 C121 C126 C125 2.1(12) . . . . ?
C127 C121 C126 C125 178.2(8) . . . . ?
C122 C121 C127 O121 12.5(12) . . . . ?
C126 C121 C127 O121 -163.5(8) . . . . ?
C122 C121 C127 O122 -166.7(7) . . . . ?
C126 C121 C127 O122 17.3(11) . . . . ?
C134 N131 C131 C132 53.9(8) . . . . ?
C135 N131 C131 C132 -65.8(7) . . . . ?
C133 N132 C132 C131 -65.8(8) . . . . ?
C136 N132 C132 C131 53.6(8) . . . . ?
N131 C131 C132 N132 10.9(8) . . . . ?
C132 N132 C133 C134 52.5(8) . . . . ?
C136 N132 C133 C134 -67.3(8) . . . . ?
C131 N131 C134 C133 -65.9(7) . . . . ?
C135 N131 C134 C133 53.9(7) . . . . ?
N132 C133 C134 N131 11.3(8) . . . . ?
C131 N131 C135 C136 52.5(7) . . . . ?
C134 N131 C135 C136 -67.1(7) . . . . ?
C132 N132 C136 C135 -65.8(7) . . . . ?
C133 N132 C136 C135 53.8(8) . . . . ?
N131 C135 C136 N132 10.9(8) . . . . ?
C145 N141 C141 C142 -58.8(8) . . . . ?
C144 N141 C141 C142 59.3(8) . . . . ?
C143 N142 C142 C141 -60.6(8) . . . . ?
C146 N142 C142 C141 60.3(8) . . . . ?
N141 C141 C142 N142 -0.6(9) . . . . ?
C142 N142 C143 C144 62.8(8) . . . . ?
C146 N142 C143 C144 -59.2(8) . . . . ?
C141 N141 C144 C143 -57.0(8) . . . . ?
C145 N141 C144 C143 62.0(7) . . . . ?
N142 C143 C144 N141 -3.5(8) . . . . ?
C141 N141 C145 C146 60.9(7) . . . . ?
C144 N141 C145 C146 -58.5(7) . . . . ?
C143 N142 C146 C145 62.8(8) . . . . ?
C142 N142 C146 C145 -58.1(8) . . . . ?
N141 C145 C146 N142 -2.7(8) . . . . ?
C155 N151 C151 C152 56.3(8) . . . . ?
C154 N151 C151 C152 -61.8(8) . . . . ?
C156 N152 C152 C151 -60.0(8) . . . . ?
C153 N152 C152 C151 58.6(8) . . . . ?
N151 C151 C152 N152 3.9(9) . . . . ?
C156 N152 C153 C154 57.2(8) . . . . ?
C152 N152 C153 C154 -63.3(8) . . . . ?
C155 N151 C154 C153 -63.3(8) . . . . ?
C151 N151 C154 C153 56.7(8) . . . . ?
N152 C153 C154 N151 5.5(9) . . . . ?
C151 N151 C155 C156 -62.2(8) . . . . ?
C154 N151 C155 C156 56.6(8) . . . . ?
C152 N152 C156 C155 54.2(8) . . . . ?
C153 N152 C156 C155 -64.4(7) . . . . ?
N151 C155 C156 N152 5.8(9) . . . . ?
C165 N161 C161 C162 64.8(8) . . . . ?
C164 N161 C161 C162 -52.4(7) . . . . ?
C163 N162 C162 C161 67.5(8) . . . . ?
C166 N162 C162 C161 -50.7(8) . . . . ?
N161 C161 C162 N162 -11.5(9) . . . . ?
C162 N162 C163 C164 -51.8(8) . . . . ?
C166 N162 C163 C164 65.4(8) . . . . ?
C165 N161 C164 C163 -50.9(8) . . . . ?
C161 N161 C164 C163 66.5(7) . . . . ?
N162 C163 C164 N161 -12.4(8) . . . . ?
C161 N161 C165 C166 -51.2(8) . . . . ?
C164 N161 C165 C166 64.7(8) . . . . ?
C163 N162 C166 C165 -53.0(8) . . . . ?
C162 N162 C166 C165 64.5(8) . . . . ?
N161 C165 C166 N162 -12.2(9) . . . . ?
C175 N171 C171 C172 64.8(7) . . . . ?
C174 N171 C171 C172 -53.8(7) . . . . ?
C176 N172 C172 C171 -54.0(7) . . . . ?
C173 N172 C172 C171 67.6(8) . . . . ?
N171 C171 C172 N172 -10.3(8) . . . . ?
C176 N172 C173 C174 66.9(7) . . . . ?
C172 N172 C173 C174 -55.7(8) . . . . ?
C175 N171 C174 C173 -52.9(8) . . . . ?
C171 N171 C174 C173 65.2(7) . . . . ?
N172 C173 C174 N171 -9.9(8) . . . . ?
C174 N171 C175 C176 63.7(7) . . . . ?
C171 N171 C175 C176 -54.1(7) . . . . ?
C172 N172 C176 C175 64.8(7) . . . . ?
C173 N172 C176 C175 -56.6(8) . . . . ?
N171 C175 C176 N172 -7.9(8) . . . . ?
C184 N181 C181 C182 55.1(8) . . . . ?
C185 N181 C181 C182 -63.6(8) . . . . ?
C186 N182 C182 C181 56.3(8) . . . . ?
C183 N182 C182 C181 -63.9(8) . . . . ?
N181 C181 C182 N182 8.0(9) . . . . ?
C182 N182 C183 C184 51.7(8) . . . . ?
C186 N182 C183 C184 -68.0(8) . . . . ?
C181 N181 C184 C183 -66.0(8) . . . . ?
C185 N181 C184 C183 52.8(8) . . . . ?
N182 C183 C184 N181 11.9(9) . . . . ?
C184 N181 C185 C186 -66.3(8) . . . . ?
C181 N181 C185 C186 52.0(8) . . . . ?
C182 N182 C186 C185 -66.7(8) . . . . ?
C183 N182 C186 C185 54.7(8) . . . . ?
N181 C185 C186 N182 10.9(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N131 H13M O12 0.93 1.63 2.556(7) 175.6 .
N132 H13N O72 0.93 1.70 2.623(8) 171.9 .
N141 H14M O22 0.93 1.60 2.523(8) 173.4 .
N142 H14N O82 0.93 1.64 2.572(8) 175.6 .
N151 H15M O32 0.93 1.62 2.549(8) 174.5 .
N152 H15N O92 0.93 1.63 2.560(8) 175.6 .
N161 H16M O42 0.93 1.66 2.586(8) 171.3 .
N162 H16N O102 0.93 1.61 2.543(8) 178.0 .
N171 H17M O52 0.93 1.66 2.583(8) 175.2 .
N172 H17N O112 0.93 1.63 2.564(8) 176.7 .
N181 H18M O62 0.93 1.63 2.554(8) 177.4 .
N182 H18N O122 0.93 1.66 2.593(8) 176.1 .

#=============================================================================

data_1b
_database_code_depnum_ccdc_archive 'CCDC 692777'

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H14 N2 2+, 2(C7 H5 O2 -)'
_chemical_formula_sum            'C20 H24 N2 O4'
_chemical_formula_weight         356.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

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

_cell_length_a                   9.2621(6)
_cell_length_b                   11.5931(7)
_cell_length_c                   34.720(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3728.1(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    8532
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      23.55

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1520
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.898
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   
;
SADABS v.2.10 (Sheldrick, 2003)
Ratio of minimum to maximum apparent transmission: 0.906444
;

_exptl_special_details           
;
H atom positions uncertain - placed on N.
;

_diffrn_ambient_temperature      180(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-Nonius X8APEX-II CCD'
_diffrn_measurement_method       'thin-slice ω and φ scans'
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            37128
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         3.51
_diffrn_reflns_theta_max         25.03
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.998
_reflns_number_total             3280
_reflns_number_gt                2450
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 v.1.0-22 (Bruker Nonius, 2004)'
_computing_cell_refinement       'SAINT v.7.06a (Bruker, 2003)'
_computing_data_reduction        'SAINT v.7.06a'
_computing_structure_solution    'SHELXTL v.6.10 (Sheldrick, 2000)'
_computing_structure_refinement  'SHELXTL v.6.10'
_computing_molecular_graphics    'SHELXTL v.6.10'
_computing_publication_material  'SHELXTL v.6.10'

_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)+(0.0516P)²+1.1313P] 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         3280
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.1060
_refine_ls_wR_factor_gt          0.0965
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.035

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
O11 O 0.62430(14) 0.71555(10) 0.52862(3) 0.0415(3) Uani 1 1 d . . .
O12 O 0.70126(15) 0.88532(11) 0.50677(4) 0.0515(4) Uani 1 1 d . . .
C11 C 0.65070(16) 0.86692(13) 0.57368(5) 0.0263(4) Uani 1 1 d . . .
C12 C 0.66633(18) 0.98394(14) 0.58139(5) 0.0339(4) Uani 1 1 d . . .
H12 H 0.6824 1.0367 0.5609 0.041 Uiso 1 1 calc R . .
C13 C 0.6584(2) 1.02352(15) 0.61890(6) 0.0410(5) Uani 1 1 d . . .
H13 H 0.6675 1.1037 0.6239 0.049 Uiso 1 1 calc R . .
C14 C 0.63763(19) 0.94803(16) 0.64914(5) 0.0407(5) Uani 1 1 d . . .
H14 H 0.6338 0.9760 0.6748 0.049 Uiso 1 1 calc R . .
C15 C 0.62248(18) 0.83151(15) 0.64176(5) 0.0363(4) Uani 1 1 d . . .
H15 H 0.6085 0.7788 0.6624 0.044 Uiso 1 1 calc R . .
C16 C 0.62773(16) 0.79184(14) 0.60411(5) 0.0295(4) Uani 1 1 d . . .
H16 H 0.6154 0.7119 0.5991 0.035 Uiso 1 1 calc R . .
C17 C 0.66015(17) 0.82169(14) 0.53297(5) 0.0314(4) Uani 1 1 d . . .
O21 O 0.60186(13) 0.49417(10) 0.32203(3) 0.0390(3) Uani 1 1 d . . .
O22 O 0.74375(16) 0.35852(11) 0.34651(4) 0.0497(4) Uani 1 1 d . . .
C21 C 0.64306(17) 0.32735(14) 0.28433(5) 0.0305(4) Uani 1 1 d . . .
C22 C 0.56765(18) 0.37365(14) 0.25345(5) 0.0348(4) Uani 1 1 d . . .
H22 H 0.5294 0.4495 0.2551 0.042 Uiso 1 1 calc R . .
C23 C 0.5480(2) 0.30976(16) 0.22030(5) 0.0435(5) Uani 1 1 d . . .
H23 H 0.4963 0.3417 0.1992 0.052 Uiso 1 1 calc R . .
C24 C 0.6037(2) 0.19944(17) 0.21782(6) 0.0478(5) Uani 1 1 d . . .
H24 H 0.5906 0.1556 0.1950 0.057 Uiso 1 1 calc R . .
C25 C 0.6782(2) 0.15276(16) 0.24849(6) 0.0481(5) Uani 1 1 d . . .
H25 H 0.7156 0.0766 0.2468 0.058 Uiso 1 1 calc R . .
C26 C 0.69835(19) 0.21636(15) 0.28154(5) 0.0391(4) Uani 1 1 d . . .
H26 H 0.7503 0.1841 0.3025 0.047 Uiso 1 1 calc R . .
C27 C 0.66772(18) 0.39431(14) 0.32042(5) 0.0317(4) Uani 1 1 d . . .
N31 N 0.62860(13) 0.58570(10) 0.38926(4) 0.0256(3) Uani 1 1 d . . .
H31C H 0.6277 0.5610 0.3638 0.031 Uiso 1 1 calc R . .
N32 N 0.63070(14) 0.65198(11) 0.45826(4) 0.0296(3) Uani 1 1 d . . .
H32C H 0.6313 0.6765 0.4838 0.036 Uiso 1 1 calc R . .
C31 C 0.57085(19) 0.49412(13) 0.41433(5) 0.0321(4) Uani 1 1 d . . .
H31B H 0.6357 0.4263 0.4136 0.038 Uiso 1 1 calc R . .
H31A H 0.4746 0.4699 0.4049 0.038 Uiso 1 1 calc R . .
C32 C 0.55844(18) 0.53818(14) 0.45563(5) 0.0313(4) Uani 1 1 d . . .
H32B H 0.4555 0.5457 0.4629 0.038 Uiso 1 1 calc R . .
H32A H 0.6048 0.4830 0.4735 0.038 Uiso 1 1 calc R . .
C33 C 0.78171(17) 0.64106(15) 0.44420(5) 0.0338(4) Uani 1 1 d . . .
H33B H 0.8320 0.5787 0.4583 0.041 Uiso 1 1 calc R . .
H33A H 0.8346 0.7141 0.4486 0.041 Uiso 1 1 calc R . .
C34 C 0.77770(16) 0.61320(14) 0.40100(5) 0.0313(4) Uani 1 1 d . . .
H34B H 0.8133 0.6802 0.3861 0.038 Uiso 1 1 calc R . .
H34A H 0.8415 0.5467 0.3955 0.038 Uiso 1 1 calc R . .
C35 C 0.55176(18) 0.73737(14) 0.43428(5) 0.0323(4) Uani 1 1 d . . .
H35B H 0.6050 0.8114 0.4338 0.039 Uiso 1 1 calc R . .
H35A H 0.4547 0.7515 0.4453 0.039 Uiso 1 1 calc R . .
C36 C 0.53792(17) 0.68955(13) 0.39334(4) 0.0292(4) Uani 1 1 d . . .
H36B H 0.4359 0.6699 0.3880 0.035 Uiso 1 1 calc R . .
H36A H 0.5689 0.7487 0.3745 0.035 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O11 C17 1.283(2) . ?
O12 C17 1.232(2) . ?
C11 C16 1.385(2) . ?
C11 C12 1.390(2) . ?
C11 C17 1.510(2) . ?
C12 C13 1.383(2) . ?
C12 H12 0.950 . ?
C13 C14 1.380(3) . ?
C13 H13 0.950 . ?
C14 C15 1.382(3) . ?
C14 H14 0.950 . ?
C15 C16 1.387(2) . ?
C15 H15 0.950 . ?
C16 H16 0.950 . ?
O21 C27 1.3098(19) . ?
O22 C27 1.220(2) . ?
C21 C22 1.387(2) . ?
C21 C26 1.388(2) . ?
C21 C27 1.492(2) . ?
C22 C23 1.381(2) . ?
C22 H22 0.950 . ?
C23 C24 1.382(3) . ?
C23 H23 0.950 . ?
C24 C25 1.379(3) . ?
C24 H24 0.950 . ?
C25 C26 1.377(3) . ?
C25 H25 0.950 . ?
C26 H26 0.950 . ?
N31 C31 1.4733(19) . ?
N31 C34 1.475(2) . ?
N31 C36 1.4747(19) . ?
N31 H31C 0.930 . ?
N32 C32 1.482(2) . ?
N32 C35 1.486(2) . ?
N32 C33 1.487(2) . ?
N32 H32C 0.930 . ?
C31 C32 1.527(2) . ?
C31 H31B 0.990 . ?
C31 H31A 0.990 . ?
C32 H32B 0.990 . ?
C32 H32A 0.990 . ?
C33 C34 1.535(2) . ?
C33 H33B 0.990 . ?
C33 H33A 0.990 . ?
C34 H34B 0.990 . ?
C34 H34A 0.990 . ?
C35 C36 1.531(2) . ?
C35 H35B 0.990 . ?
C35 H35A 0.990 . ?
C36 H36B 0.990 . ?
C36 H36A 0.990 . ?

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
C16 C11 C12 118.84(15) . . ?
C16 C11 C17 120.30(14) . . ?
C12 C11 C17 120.86(15) . . ?
C13 C12 C11 119.97(16) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C12 120.89(16) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 119.53(17) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C16 119.69(17) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C11 C16 C15 121.06(15) . . ?
C11 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
O12 C17 O11 124.55(16) . . ?
O12 C17 C11 120.09(15) . . ?
O11 C17 C11 115.35(15) . . ?
C22 C21 C26 119.37(16) . . ?
C22 C21 C27 121.66(14) . . ?
C26 C21 C27 118.97(15) . . ?
C23 C22 C21 120.18(16) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C24 119.96(18) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C25 C24 C23 120.12(17) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C26 C25 C24 120.08(17) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 C21 120.29(17) . . ?
C25 C26 H26 119.9 . . ?
C21 C26 H26 119.9 . . ?
O22 C27 O21 122.55(16) . . ?
O22 C27 C21 122.35(15) . . ?
O21 C27 C21 115.10(14) . . ?
C31 N31 C34 109.42(12) . . ?
C31 N31 C36 108.95(12) . . ?
C34 N31 C36 109.29(12) . . ?
C31 N31 H31C 109.7 . . ?
C34 N31 H31C 109.7 . . ?
C36 N31 H31C 109.7 . . ?
C32 N32 C35 109.67(12) . . ?
C32 N32 C33 109.20(12) . . ?
C35 N32 C33 109.62(13) . . ?
C32 N32 H32C 109.4 . . ?
C35 N32 H32C 109.4 . . ?
C33 N32 H32C 109.4 . . ?
N31 C31 C32 109.94(12) . . ?
N31 C31 H31B 109.7 . . ?
C32 C31 H31B 109.7 . . ?
N31 C31 H31A 109.7 . . ?
C32 C31 H31A 109.7 . . ?
H31B C31 H31A 108.2 . . ?
N32 C32 C31 108.75(12) . . ?
N32 C32 H32B 109.9 . . ?
C31 C32 H32B 109.9 . . ?
N32 C32 H32A 109.9 . . ?
C31 C32 H32A 109.9 . . ?
H32B C32 H32A 108.3 . . ?
N32 C33 C34 108.41(13) . . ?
N32 C33 H33B 110.0 . . ?
C34 C33 H33B 110.0 . . ?
N32 C33 H33A 110.0 . . ?
C34 C33 H33A 110.0 . . ?
H33B C33 H33A 108.4 . . ?
N31 C34 C33 109.77(12) . . ?
N31 C34 H34B 109.7 . . ?
C33 C34 H34B 109.7 . . ?
N31 C34 H34A 109.7 . . ?
C33 C34 H34A 109.7 . . ?
H34B C34 H34A 108.2 . . ?
N32 C35 C36 108.66(12) . . ?
N32 C35 H35B 110.0 . . ?
C36 C35 H35B 110.0 . . ?
N32 C35 H35A 110.0 . . ?
C36 C35 H35A 110.0 . . ?
H35B C35 H35A 108.3 . . ?
N31 C36 C35 109.70(12) . . ?
N31 C36 H36B 109.7 . . ?
C35 C36 H36B 109.7 . . ?
N31 C36 H36A 109.7 . . ?
C35 C36 H36A 109.7 . . ?
H36B C36 H36A 108.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 C11 C12 C13 -0.2(2) . . . . ?
C17 C11 C12 C13 -179.50(15) . . . . ?
C11 C12 C13 C14 1.1(3) . . . . ?
C12 C13 C14 C15 -0.9(3) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
C12 C11 C16 C15 -1.0(2) . . . . ?
C17 C11 C16 C15 178.32(14) . . . . ?
C14 C15 C16 C11 1.2(2) . . . . ?
C16 C11 C17 O12 -169.37(15) . . . . ?
C12 C11 C17 O12 9.9(2) . . . . ?
C16 C11 C17 O11 10.0(2) . . . . ?
C12 C11 C17 O11 -170.67(15) . . . . ?
C26 C21 C22 C23 -0.1(2) . . . . ?
C27 C21 C22 C23 179.32(16) . . . . ?
C21 C22 C23 C24 0.0(3) . . . . ?
C22 C23 C24 C25 0.3(3) . . . . ?
C23 C24 C25 C26 -0.5(3) . . . . ?
C24 C25 C26 C21 0.5(3) . . . . ?
C22 C21 C26 C25 -0.2(3) . . . . ?
C27 C21 C26 C25 -179.56(16) . . . . ?
C22 C21 C27 O22 -173.80(17) . . . . ?
C26 C21 C27 O22 5.6(3) . . . . ?
C22 C21 C27 O21 6.2(2) . . . . ?
C26 C21 C27 O21 -174.45(15) . . . . ?
C34 N31 C31 C32 64.98(16) . . . . ?
C36 N31 C31 C32 -54.44(17) . . . . ?
C35 N32 C32 C31 65.17(16) . . . . ?
C33 N32 C32 C31 -54.97(17) . . . . ?
N31 C31 C32 N32 -9.16(18) . . . . ?
C32 N32 C33 C34 66.16(16) . . . . ?
C35 N32 C33 C34 -54.01(17) . . . . ?
C31 N31 C34 C33 -53.39(16) . . . . ?
C36 N31 C34 C33 65.83(16) . . . . ?
N32 C33 C34 N31 -10.22(18) . . . . ?
C32 N32 C35 C36 -53.96(16) . . . . ?
C33 N32 C35 C36 65.92(16) . . . . ?
C31 N31 C36 C35 65.70(16) . . . . ?
C34 N31 C36 C35 -53.81(16) . . . . ?
N32 C35 C36 N31 -10.06(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N31 H31C O21 0.93 1.66 2.5762(17) 167.2 .
N32 H32C O11 0.93 1.62 2.5526(17) 176.9 .

#=============================================================================

data_2
_database_code_depnum_ccdc_archive 'CCDC 692778'

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H12 N2 2+, 2(C7 H5 O2 -)'
_chemical_formula_sum            'C18 H22 N2 O4'
_chemical_formula_weight         330.38

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'
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           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

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

_cell_length_a                   8.346(2)
_cell_length_b                   8.243(2)
_cell_length_c                   24.679(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1697.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    543
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      20.18

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.474
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_process_details   
;
SADABS v.2.10 (Sheldrick, 2003)
Ratio of minimum to maximum apparent transmission: 0.474551
;

_exptl_special_details           
;
Weak diffractor. Data are truncated (optimistically) to 0.95 Å
resolution, with ca 50% observed at the I>2σ(I) level. The
structure is therefore of relatively low precision.

H atoms associated with the N atoms of the piperazine group
were visible in difference Fourier maps (and could be refined
stably) but were placd geometrically and refined using a riding
model on account of the low data resolution and low
data-to-parameter ratio.
;

_diffrn_ambient_temperature      180(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-Nonius X8APEX-II CCD'
_diffrn_measurement_method       'thin-slice ω and φ scans'
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5734
_diffrn_reflns_av_R_equivalents  0.1083
_diffrn_reflns_av_sigmaI/netI    0.0877
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.57
_diffrn_reflns_theta_max         22.08
_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        22.08
_diffrn_measured_fraction_theta_full 0.983
_reflns_number_total             1035
_reflns_number_gt                588
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 v.1.0-22 (Bruker Nonius, 2004)'
_computing_cell_refinement       'SAINT v.7.06a (Bruker, 2003)'
_computing_data_reduction        'SAINT v.7.06a'
_computing_structure_solution    'SHELXTL v.6.10 (Sheldrick, 2000)'
_computing_structure_refinement  'SHELXTL v.6.10'
_computing_molecular_graphics    'SHELXTL v.6.10'
_computing_publication_material  'SHELXTL v.6.10'

_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)+(0.0997P)²+0.1300P] 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         1035
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1301
_refine_ls_R_factor_gt           0.0671
_refine_ls_wR_factor_ref         0.1917
_refine_ls_wR_factor_gt          0.1652
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.061

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3320(4) 0.5117(4) 0.43510(15) 0.0430(11) Uani 1 1 d . . .
O2 O 0.5553(4) 0.6287(4) 0.40592(16) 0.0493(12) Uani 1 1 d . . .
C1 C 0.4799(6) 0.3841(6) 0.3640(2) 0.0335(14) Uani 1 1 d . . .
C2 C 0.3673(6) 0.2646(6) 0.3552(2) 0.0409(15) Uani 1 1 d . . .
H2A H 0.2703 0.2654 0.3754 0.049 Uiso 1 1 calc R . .
C3 C 0.3940(7) 0.1424(6) 0.3171(2) 0.0462(16) Uani 1 1 d . . .
H3A H 0.3153 0.0610 0.3112 0.055 Uiso 1 1 calc R . .
C4 C 0.5332(7) 0.1406(7) 0.2886(3) 0.0527(17) Uani 1 1 d . . .
H4A H 0.5524 0.0571 0.2629 0.063 Uiso 1 1 calc R . .
C5 C 0.6469(7) 0.2598(7) 0.2968(2) 0.0590(18) Uani 1 1 d . . .
H5A H 0.7439 0.2590 0.2767 0.071 Uiso 1 1 calc R . .
C6 C 0.6181(7) 0.3811(7) 0.3348(2) 0.0478(17) Uani 1 1 d . . .
H6A H 0.6963 0.4631 0.3405 0.057 Uiso 1 1 calc R . .
C7 C 0.4530(7) 0.5163(6) 0.4052(2) 0.0366(14) Uani 1 1 d . . .
N1 N 0.4632(4) 0.8842(4) 0.45897(19) 0.0370(12) Uani 1 1 d . . .
H1A H 0.3649 0.9200 0.4470 0.044 Uiso 1 1 calc R . .
H1B H 0.4899 0.7933 0.4393 0.044 Uiso 1 1 calc R . .
C8 C 0.5846(6) 1.0123(6) 0.4495(2) 0.0396(15) Uani 1 1 d . . .
H8A H 0.5850 1.0428 0.4107 0.047 Uiso 1 1 calc R . .
H8B H 0.6923 0.9703 0.4588 0.047 Uiso 1 1 calc R . .
C9 C 0.4519(6) 0.8414(5) 0.5166(2) 0.0388(16) Uani 1 1 d . . .
H9A H 0.5545 0.7930 0.5287 0.047 Uiso 1 1 calc R . .
H9B H 0.3666 0.7594 0.5217 0.047 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.251(6) . ?
O2 C7 1.260(5) . ?
C1 C6 1.360(7) . ?
C1 C2 1.378(6) . ?
C1 C7 1.508(7) . ?
C2 C3 1.396(7) . ?
C2 H2A 0.9500 . ?
C3 C4 1.359(8) . ?
C3 H3A 0.9500 . ?
C4 C5 1.381(7) . ?
C4 H4A 0.9500 . ?
C5 C6 1.392(8) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
N1 C9 1.469(6) . ?
N1 C8 1.482(5) . ?
N1 H1A 0.9200 . ?
N1 H1B 0.9200 . ?
C8 C9 1.499(7) 5_676 ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C8 1.499(7) 5_676 ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?

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
C6 C1 C2 118.9(5) . . ?
C6 C1 C7 119.7(5) . . ?
C2 C1 C7 121.4(5) . . ?
C1 C2 C3 120.8(5) . . ?
C1 C2 H2A 119.6 . . ?
C3 C2 H2A 119.6 . . ?
C4 C3 C2 119.5(5) . . ?
C4 C3 H3A 120.2 . . ?
C2 C3 H3A 120.2 . . ?
C3 C4 C5 120.3(5) . . ?
C3 C4 H4A 119.9 . . ?
C5 C4 H4A 119.9 . . ?
C4 C5 C6 119.5(5) . . ?
C4 C5 H5A 120.3 . . ?
C6 C5 H5A 120.3 . . ?
C1 C6 C5 121.0(5) . . ?
C1 C6 H6A 119.5 . . ?
C5 C6 H6A 119.5 . . ?
O1 C7 O2 124.1(5) . . ?
O1 C7 C1 119.8(5) . . ?
O2 C7 C1 116.1(5) . . ?
C9 N1 C8 111.6(4) . . ?
C9 N1 H1A 109.3 . . ?
C8 N1 H1A 109.3 . . ?
C9 N1 H1B 109.3 . . ?
C8 N1 H1B 109.3 . . ?
H1A N1 H1B 108.0 . . ?
N1 C8 C9 110.2(4) . 5_676 ?
N1 C8 H8A 109.6 . . ?
C9 C8 H8A 109.6 5_676 . ?
N1 C8 H8B 109.6 . . ?
C9 C8 H8B 109.6 5_676 . ?
H8A C8 H8B 108.1 . . ?
N1 C9 C8 111.1(4) . 5_676 ?
N1 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 5_676 . ?
N1 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 5_676 . ?
H9A C9 H9B 108.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.1(8) . . . . ?
C7 C1 C2 C3 -179.7(5) . . . . ?
C1 C2 C3 C4 0.5(8) . . . . ?
C2 C3 C4 C5 -0.7(8) . . . . ?
C3 C4 C5 C6 0.4(9) . . . . ?
C2 C1 C6 C5 -0.2(8) . . . . ?
C7 C1 C6 C5 179.5(5) . . . . ?
C4 C5 C6 C1 0.0(9) . . . . ?
C6 C1 C7 O1 -174.2(5) . . . . ?
C2 C1 C7 O1 5.4(7) . . . . ?
C6 C1 C7 O2 7.6(7) . . . . ?
C2 C1 C7 O2 -172.7(5) . . . . ?
C9 N1 C8 C9 -56.1(6) . . . 5_676 ?
C8 N1 C9 C8 56.6(5) . . . 5_676 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1B O2 0.92 1.68 2.596(5) 174.8 .
N1 H1A O1 0.92 1.83 2.742(5) 169.4 8_665

#=============================================================================

data_3a
_database_code_depnum_ccdc_archive 'CCDC 692779'

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C7 H6 O2), C4 H5 N3'
_chemical_formula_sum            'C18 H17 N3 O4'
_chemical_formula_weight         339.35

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   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   13.9348(18)
_cell_length_b                   8.8620(11)
_cell_length_c                   14.1261(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.712(4)
_cell_angle_gamma                90.00
_cell_volume                     1714.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    3413
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      21.30

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.766
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_process_details   
;
TWINABS v.1.05 (Sheldrick, 2003)
Ratio of minimum to maximum apparent transmission: 0.766880
;

_exptl_special_details           
;
Crystal twinned by 180 deg. rotation about c.
HKLF 5 refinement. Refined BASF 0.4565(5).

Statistics for singles for twin component 1
#-------------------------------------------
Run 2-theta R(int) Incid. factors Diffr. factors K Total I>2sig(I)
1 -14.0 0.0638 0.949 - 1.030 0.973 - 1.250 0.455 5652 3150
2 -14.0 0.0683 0.939 - 1.018 0.973 - 1.091 0.417 7395 3786
3 -8.0 0.0568 0.965 - 1.031 0.965 - 1.053 0.433 930 531

Statistics for singles for twin component 2
#-------------------------------------------
Run 2-theta R(int) Incid. factors Diffr. factors K Total I>2sig(I)
1 -14.0 0.0713 0.949 - 1.030 0.973 - 1.257 0.447 5643 3005
2 -14.0 0.0789 0.939 - 1.017 0.973 - 1.097 0.422 7386 3588
3 -8.0 0.0700 0.965 - 1.031 0.967 - 1.054 0.475 924 480

Statistics for all composite reflections
#---------------------------------------
Run 2-theta R(int) Incid. factors Diffr. factors K Total I>2sig(I)
1 -14.0 0.0779 0.950 - 1.030 0.973 - 1.258 0.412 2919 1767
2 -14.0 0.0779 0.939 - 1.017 0.973 - 1.091 0.379 4006 2190
3 -8.0 0.0716 0.965 - 1.031 0.973 - 1.055 0.443 382 242

Statistics for all single and composite reflections
#--------------------------------------------------
Run 2-theta R(int) Incid. factors Diffr. factors K Total I>2sig(I)
1 -14.0 0.0698 0.949 - 1.030 0.973 - 1.258 0.443 14214 7895
2 -14.0 0.0743 0.939 - 1.018 0.973 - 1.097 0.411 18787 9564
3 -8.0 0.0644 0.965 - 1.031 0.965 - 1.055 0.452 2236 1257

su = K * Sqrt[ sigma^2(I) + (g)^2 ] where sigma(I) is estimated by SAINT

The above statistics are based on all non-rejected data, ignoring
reflections without equivalents when estimating R(int) and K.
;

_diffrn_ambient_temperature      180(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-Nonius X8APEX-II CCD'
_diffrn_measurement_method       'thin-slice ω and φ scans'
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5544
_diffrn_reflns_av_R_equivalents  0.0000
# data merged within TWINABS - see statistics above
_diffrn_reflns_av_sigmaI/netI    0.1838
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.53
_diffrn_reflns_theta_max         25.07
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.07
_diffrn_measured_fraction_theta_full 0.995
_reflns_number_total             5544
_reflns_number_gt                2324
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 v.1.0-22 (Bruker Nonius, 2004)'
_computing_cell_refinement       'SAINTPLUS v.7.06a (Bruker, 2003)'
_computing_data_reduction        'SAINTPLUS v.7.06a'
_computing_structure_solution    'SHELXTL v.6.10 (Sheldrick, 2000)'
_computing_structure_refinement  'SHELXTL v.6.10'
_computing_molecular_graphics    'SHELXTL v.6.10'
_computing_publication_material  'SHELXTL v.6.10'

_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)+(0.0263P)²] 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         5544
_refine_ls_number_parameters     243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1135
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.0674
_refine_ls_wR_factor_gt          0.0612
_refine_ls_goodness_of_fit_ref   0.682
_refine_ls_restrained_S_all      0.682
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.038

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
O11 O 0.41635(9) 0.85867(13) 0.58284(8) 0.0433(4) Uani 1 1 d . . .
O12 O 0.37884(9) 0.89561(14) 0.42376(8) 0.0391(4) Uani 1 1 d . . .
H12 H 0.4296(14) 0.819(2) 0.4251(12) 0.083(8) Uiso 1 1 d . . .
C11 C 0.29266(13) 1.03770(18) 0.52074(13) 0.0277(5) Uani 1 1 d . . .
C12 C 0.23636(13) 1.10190(19) 0.43955(13) 0.0388(5) Uani 1 1 d . . .
H12A H 0.2473 1.0745 0.3774 0.047 Uiso 1 1 calc R . .
C13 C 0.16465(15) 1.2052(2) 0.44835(15) 0.0525(6) Uani 1 1 d . . .
H13A H 0.1260 1.2487 0.3925 0.063 Uiso 1 1 calc R . .
C14 C 0.14945(14) 1.2450(2) 0.53864(17) 0.0555(6) Uani 1 1 d . . .
H14A H 0.0999 1.3161 0.5448 0.067 Uiso 1 1 calc R . .
C15 C 0.20494(15) 1.1832(2) 0.61994(15) 0.0514(6) Uani 1 1 d . . .
H15A H 0.1938 1.2116 0.6818 0.062 Uiso 1 1 calc R . .
C16 C 0.27683(14) 1.07984(19) 0.61148(13) 0.0403(5) Uani 1 1 d . . .
H16A H 0.3156 1.0374 0.6676 0.048 Uiso 1 1 calc R . .
C17 C 0.36860(13) 0.92293(19) 0.51334(14) 0.0314(5) Uani 1 1 d . . .
O21 O 0.71905(9) 0.44494(13) 0.67623(8) 0.0447(4) Uani 1 1 d . . .
O22 O 0.78413(9) 0.37250(14) 0.55075(9) 0.0404(4) Uani 1 1 d . . .
H22 H 0.7295(14) 0.4341(19) 0.5108(13) 0.081(7) Uiso 1 1 d . . .
C21 C 0.84592(13) 0.26203(18) 0.70169(12) 0.0264(4) Uani 1 1 d . . .
C22 C 0.91103(13) 0.17424(19) 0.66218(12) 0.0365(5) Uani 1 1 d . . .
H22A H 0.9134 0.1829 0.5956 0.044 Uiso 1 1 calc R . .
C23 C 0.97248(13) 0.07420(19) 0.71934(14) 0.0414(5) Uani 1 1 d . . .
H23A H 1.0170 0.0148 0.6919 0.050 Uiso 1 1 calc R . .
C24 C 0.96937(13) 0.06040(19) 0.81565(14) 0.0401(5) Uani 1 1 d . . .
H24A H 1.0114 -0.0087 0.8547 0.048 Uiso 1 1 calc R . .
C25 C 0.90472(13) 0.14761(19) 0.85559(13) 0.0385(5) Uani 1 1 d . . .
H25A H 0.9025 0.1385 0.9221 0.046 Uiso 1 1 calc R . .
C26 C 0.84339(12) 0.24803(19) 0.79871(12) 0.0326(5) Uani 1 1 d . . .
H26A H 0.7992 0.3078 0.8265 0.039 Uiso 1 1 calc R . .
C27 C 0.77677(14) 0.3684(2) 0.64247(13) 0.0336(5) Uani 1 1 d . . .
N1 N 0.50958(10) 0.69575(14) 0.39978(10) 0.0279(4) Uani 1 1 d . . .
N2 N 0.64407(10) 0.52627(15) 0.44141(10) 0.0300(4) Uani 1 1 d . . .
N3 N 0.57829(13) 0.65004(19) 0.55800(11) 0.0320(4) Uani 1 1 d . . .
H31 H 0.6184(12) 0.5948(16) 0.6004(10) 0.040(6) Uiso 1 1 d . . .
H32 H 0.5303(12) 0.7132(19) 0.5717(11) 0.058(7) Uiso 1 1 d . . .
C1 C 0.57797(14) 0.62298(19) 0.46444(13) 0.0279(5) Uani 1 1 d . . .
C2 C 0.63933(13) 0.49908(18) 0.34794(14) 0.0375(5) Uani 1 1 d . . .
H2A H 0.6853 0.4313 0.3294 0.045 Uiso 1 1 calc R . .
C3 C 0.57136(13) 0.56415(19) 0.27724(12) 0.0363(5) Uani 1 1 d . . .
H3A H 0.5686 0.5421 0.2110 0.044 Uiso 1 1 calc R . .
C4 C 0.50768(13) 0.66272(18) 0.30754(12) 0.0339(5) Uani 1 1 d . . .
H4A H 0.4597 0.7100 0.2603 0.041 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O11 C17 1.2199(18) . ?
O12 C17 1.3219(18) . ?
O12 H12 0.98(2) . ?
C11 C12 1.386(2) . ?
C11 C16 1.391(2) . ?
C11 C17 1.485(2) . ?
C12 C13 1.378(2) . ?
C12 H12A 0.950 . ?
C13 C14 1.377(2) . ?
C13 H13A 0.950 . ?
C14 C15 1.373(2) . ?
C14 H14A 0.950 . ?
C15 C16 1.379(2) . ?
C15 H15A 0.950 . ?
C16 H16A 0.950 . ?
O21 C27 1.2155(19) . ?
O22 C27 1.3190(18) . ?
O22 H22 1.02(2) . ?
C21 C26 1.3831(19) . ?
C21 C22 1.389(2) . ?
C21 C27 1.489(2) . ?
C22 C23 1.384(2) . ?
C22 H22A 0.950 . ?
C23 C24 1.375(2) . ?
C23 H23A 0.950 . ?
C24 C25 1.384(2) . ?
C24 H24A 0.950 . ?
C25 C26 1.3830(19) . ?
C25 H25A 0.950 . ?
C26 H26A 0.950 . ?
N1 C4 1.3310(17) . ?
N1 C1 1.3545(18) . ?
N2 C2 1.3316(17) . ?
N2 C1 1.3418(19) . ?
N3 C1 1.342(2) . ?
N3 H31 0.89(2) . ?
N3 H32 0.92(2) . ?
C2 C3 1.369(2) . ?
C2 H2A 0.950 . ?
C3 C4 1.369(2) . ?
C3 H3A 0.950 . ?
C4 H4A 0.950 . ?

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
C17 O12 H12 108.3(10) . . ?
C12 C11 C16 119.34(17) . . ?
C12 C11 C17 121.60(17) . . ?
C16 C11 C17 119.05(17) . . ?
C13 C12 C11 120.44(18) . . ?
C13 C12 H12A 119.8 . . ?
C11 C12 H12A 119.8 . . ?
C14 C13 C12 119.51(19) . . ?
C14 C13 H13A 120.2 . . ?
C12 C13 H13A 120.2 . . ?
C15 C14 C13 120.9(2) . . ?
C15 C14 H14A 119.6 . . ?
C13 C14 H14A 119.6 . . ?
C14 C15 C16 119.83(19) . . ?
C14 C15 H15A 120.1 . . ?
C16 C15 H15A 120.1 . . ?
C15 C16 C11 120.01(18) . . ?
C15 C16 H16A 120.0 . . ?
C11 C16 H16A 120.0 . . ?
O11 C17 O12 123.04(17) . . ?
O11 C17 C11 123.51(17) . . ?
O12 C17 C11 113.45(17) . . ?
C27 O22 H22 111.9(10) . . ?
C26 C21 C22 119.14(17) . . ?
C26 C21 C27 118.72(17) . . ?
C22 C21 C27 122.12(17) . . ?
C23 C22 C21 120.27(16) . . ?
C23 C22 H22A 119.9 . . ?
C21 C22 H22A 119.9 . . ?
C24 C23 C22 120.31(17) . . ?
C24 C23 H23A 119.8 . . ?
C22 C23 H23A 119.8 . . ?
C23 C24 C25 119.76(17) . . ?
C23 C24 H24A 120.1 . . ?
C25 C24 H24A 120.1 . . ?
C26 C25 C24 120.09(17) . . ?
C26 C25 H25A 120.0 . . ?
C24 C25 H25A 120.0 . . ?
C25 C26 C21 120.43(17) . . ?
C25 C26 H26A 119.8 . . ?
C21 C26 H26A 119.8 . . ?
O21 C27 O22 123.21(17) . . ?
O21 C27 C21 122.63(17) . . ?
O22 C27 C21 114.16(18) . . ?
C4 N1 C1 116.04(16) . . ?
C2 N2 C1 116.50(15) . . ?
C1 N3 H31 116.9(10) . . ?
C1 N3 H32 116.5(10) . . ?
H31 N3 H32 125.9(15) . . ?
N2 C1 N3 118.43(18) . . ?
N2 C1 N1 124.70(16) . . ?
N3 C1 N1 116.87(19) . . ?
N2 C2 C3 123.17(17) . . ?
N2 C2 H2A 118.4 . . ?
C3 C2 H2A 118.4 . . ?
C4 C3 C2 116.18(16) . . ?
C4 C3 H3A 121.9 . . ?
C2 C3 H3A 121.9 . . ?
N1 C4 C3 123.38(17) . . ?
N1 C4 H4A 118.3 . . ?
C3 C4 H4A 118.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 C11 C12 C13 -0.7(2) . . . . ?
C17 C11 C12 C13 178.28(16) . . . . ?
C11 C12 C13 C14 0.3(3) . . . . ?
C12 C13 C14 C15 0.1(3) . . . . ?
C13 C14 C15 C16 -0.1(3) . . . . ?
C14 C15 C16 C11 -0.4(3) . . . . ?
C12 C11 C16 C15 0.8(2) . . . . ?
C17 C11 C16 C15 -178.27(15) . . . . ?
C12 C11 C17 O11 -176.38(16) . . . . ?
C16 C11 C17 O11 2.6(2) . . . . ?
C12 C11 C17 O12 2.9(2) . . . . ?
C16 C11 C17 O12 -178.10(15) . . . . ?
C26 C21 C22 C23 0.0(2) . . . . ?
C27 C21 C22 C23 -178.47(15) . . . . ?
C21 C22 C23 C24 0.3(3) . . . . ?
C22 C23 C24 C25 -0.3(3) . . . . ?
C23 C24 C25 C26 0.1(3) . . . . ?
C24 C25 C26 C21 0.1(2) . . . . ?
C22 C21 C26 C25 -0.2(2) . . . . ?
C27 C21 C26 C25 178.34(15) . . . . ?
C26 C21 C27 O21 1.0(3) . . . . ?
C22 C21 C27 O21 179.48(16) . . . . ?
C26 C21 C27 O22 -179.31(15) . . . . ?
C22 C21 C27 O22 -0.8(2) . . . . ?
C2 N2 C1 N3 178.02(15) . . . . ?
C2 N2 C1 N1 -1.6(2) . . . . ?
C4 N1 C1 N2 2.3(2) . . . . ?
C4 N1 C1 N3 -177.27(15) . . . . ?
C1 N2 C2 C3 -0.2(2) . . . . ?
N2 C2 C3 C4 1.0(3) . . . . ?
C1 N1 C4 C3 -1.4(2) . . . . ?
C2 C3 C4 N1 -0.1(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O12 H12 N1 0.98(2) 1.64(2) 2.6077(18) 166.4(16) .
O22 H22 N2 1.02(2) 1.62(2) 2.6327(18) 176.4(15) .
N3 H32 O11 0.92(2) 2.074(17) 2.988(2) 172.4(14) .
N3 H31 O21 0.89(2) 2.078(16) 2.953(2) 168.9(14) .

#=============================================================================

data_3b
_database_code_depnum_ccdc_archive 'CCDC 692780'

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C7 H6 O2), C4 H5 N3'
_chemical_formula_sum            'C18 H17 N3 O4'
_chemical_formula_weight         339.35

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           orthorhombic
_symmetry_space_group_name_H-M   'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'

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

_cell_length_a                   12.5428(10)
_cell_length_b                   34.337(3)
_cell_length_c                   3.8730(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1668.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    3053
_cell_measurement_theta_min      3.25
_cell_measurement_theta_max      24.26

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.752
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   
;
SADABS v.2.10 (Sheldrick, 2003)
Ratio of minimum to maximum apparent transmission: 0.755826
;

_exptl_special_details           
;
H atom associated with benzoic acid molecule refined freely.
;

_diffrn_ambient_temperature      180(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-Nonius X8APEX-II CCD'
_diffrn_measurement_method       'thin-slice ω and φ scans'
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9518
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0222
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_theta_min         3.56
_diffrn_reflns_theta_max         25.09
_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.09
_diffrn_measured_fraction_theta_full 0.990
_reflns_number_total             1508
_reflns_number_gt                1200
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 v.1.0-22 (Bruker Nonius, 2004)'
_computing_cell_refinement       'SAINTPLUS v.7.06a (Bruker, 2003)'
_computing_data_reduction        'SAINTPLUS v.7.06a'
_computing_structure_solution    'SHELXTL v.6.10 (Sheldrick, 2000)'
_computing_structure_refinement  'SHELXTL v.6.10'
_computing_molecular_graphics    'SHELXTL v.6.10'
_computing_publication_material  'SHELXTL v.6.10'

_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)+(0.0332P)²+0.4122P] 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         1508
_refine_ls_number_parameters     126
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0767
_refine_ls_wR_factor_gt          0.0712
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.030

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
O11 O 0.33311(7) 0.67286(3) 0.1984(3) 0.0403(3) Uani 1 1 d . . .
O12 O 0.16990(7) 0.64779(3) 0.2397(3) 0.0414(3) Uani 1 1 d . . .
H12 H 0.1462(14) 0.6745(6) 0.148(5) 0.080(6) Uiso 1 1 d . . .
C11 C 0.31410(10) 0.60805(4) 0.4036(3) 0.0296(3) Uani 1 1 d . . .
C12 C 0.24409(11) 0.58006(4) 0.5299(3) 0.0349(3) Uani 1 1 d . . .
H12A H 0.1695 0.5849 0.5298 0.042 Uiso 1 1 calc R . .
C13 C 0.28281(13) 0.54526(4) 0.6553(4) 0.0418(4) Uani 1 1 d . . .
H13A H 0.2349 0.5263 0.7440 0.050 Uiso 1 1 calc R . .
C14 C 0.39075(14) 0.53789(4) 0.6524(4) 0.0453(4) Uani 1 1 d . . .
H14A H 0.4171 0.5138 0.7376 0.054 Uiso 1 1 calc R . .
C15 C 0.46068(12) 0.56547(4) 0.5259(4) 0.0441(4) Uani 1 1 d . . .
H15A H 0.5351 0.5603 0.5231 0.053 Uiso 1 1 calc R . .
C16 C 0.42268(11) 0.60065(4) 0.4034(4) 0.0362(4) Uani 1 1 d . . .
H16A H 0.4710 0.6197 0.3191 0.043 Uiso 1 1 calc R . .
C17 C 0.27409(10) 0.64598(4) 0.2708(3) 0.0304(3) Uani 1 1 d . . .
N2 N 0.09752(8) 0.71530(3) 0.0147(3) 0.0278(3) Uani 1 1 d . . .
N3 N 0.22947(12) 0.7500 0.2890(4) 0.0303(4) Uani 1 2 d S . .
H31 H 0.2660(11) 0.7283(4) 0.306(4) 0.041(4) Uiso 1 1 d . . .
C1 C 0.14033(13) 0.7500 0.0997(4) 0.0249(4) Uani 1 2 d S . .
C2 C 0.00671(10) 0.71590(4) -0.1645(3) 0.0314(3) Uani 1 1 d . . .
H2A H -0.0252 0.6919 -0.2286 0.038 Uiso 1 1 calc R . .
C3 C -0.04243(14) 0.7500 -0.2597(5) 0.0331(5) Uani 1 2 d S . .
H3A H -0.1074 0.7500 -0.3856 0.040 Uiso 1 2 calc SR . .


_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
O11 C17 1.2159(15) . ?
O12 C17 1.3138(16) . ?
O12 H12 1.03(2) . ?
C11 C16 1.3854(18) . ?
C11 C12 1.3907(19) . ?
C11 C17 1.4875(18) . ?
C12 C13 1.3783(19) . ?
C12 H12A 0.950 . ?
C13 C14 1.377(2) . ?
C13 H13A 0.950 . ?
C14 C15 1.380(2) . ?
C14 H14A 0.950 . ?
C15 C16 1.383(2) . ?
C15 H15A 0.950 . ?
C16 H16A 0.950 . ?
N2 C2 1.3340(16) . ?
N2 C1 1.3477(13) . ?
N3 C1 1.337(2) . ?
N3 H31 0.877(13) . ?
C2 C3 1.3736(16) . ?
C2 H2A 0.950 . ?
C3 H3A 0.950 . ?

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
C17 O12 H12 111.2(10) . . ?
C16 C11 C12 119.62(13) . . ?
C16 C11 C17 119.47(12) . . ?
C12 C11 C17 120.91(12) . . ?
C13 C12 C11 120.04(14) . . ?
C13 C12 H12A 120.0 . . ?
C11 C12 H12A 120.0 . . ?
C14 C13 C12 120.18(14) . . ?
C14 C13 H13A 119.9 . . ?
C12 C13 H13A 119.9 . . ?
C13 C14 C15 120.10(14) . . ?
C13 C14 H14A 120.0 . . ?
C15 C14 H14A 120.0 . . ?
C14 C15 C16 120.14(14) . . ?
C14 C15 H15A 119.9 . . ?
C16 C15 H15A 119.9 . . ?
C15 C16 C11 119.92(14) . . ?
C15 C16 H16A 120.0 . . ?
C11 C16 H16A 120.0 . . ?
O11 C17 O12 123.27(12) . . ?
O11 C17 C11 122.61(12) . . ?
O12 C17 C11 114.12(11) . . ?
C2 N2 C1 116.97(12) . . ?
C1 N3 H31 118.6(10) . . ?
N3 C1 N2 117.85(8) . 7_575 ?
N3 C1 N2 117.84(8) . . ?
N2 C1 N2 124.28(16) 7_575 . ?
N2 C2 C3 122.41(13) . . ?
N2 C2 H2A 118.8 . . ?
C3 C2 H2A 118.8 . . ?
C2 C3 C2 116.95(17) . 7_575 ?
C2 C3 H3A 121.5 . . ?
C2 C3 H3A 121.5 7_575 . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O12 H12 N2 1.03(2) 1.61(2) 2.6376(14) 174.4(17) .
N3 H31 O11 0.877(13) 2.123(14) 2.9714(12) 162.6(14) .

#=============================================================================

data_4
_database_code_depnum_ccdc_archive 'CCDC 692781'

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H6 O2, C4 H5 N3'
_chemical_formula_sum            'C11 H11 N3 O2'
_chemical_formula_weight         217.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   5.3467(4)
_cell_length_b                   17.2757(13)
_cell_length_c                   11.5764(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.980(3)
_cell_angle_gamma                90.00
_cell_volume                     1069.13(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    8371
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      26.15

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.872
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   
;
SADABS v.2.10 (Sheldrick, 2003)
Ratio of minimum to maximum apparent transmission: 0.888565
;

_exptl_special_details           ?

_diffrn_ambient_temperature      180(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-Nonius X8APEX-II CCD'
_diffrn_measurement_method       'thin-slice ω and φ scans'
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15086
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0168
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.52
_diffrn_reflns_theta_max         26.36
_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        26.36
_diffrn_measured_fraction_theta_full 0.982
_reflns_number_total             2153
_reflns_number_gt                1839
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 v.1.0-22 (Bruker Nonius, 2004)'
_computing_cell_refinement       'SAINT v.7.06a (Bruker, 2003)'
_computing_data_reduction        'SAINT v.7.06a'
_computing_structure_solution    'SHELXTL v.6.10 (Sheldrick, 2000)'
_computing_structure_refinement  'SHELXTL v.6.10'
_computing_molecular_graphics    'SHELXTL v.6.10'
_computing_publication_material  'SHELXTL v.6.10'

_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)+(0.0301P)²+0.9362P] 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         2153
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1178
_refine_ls_wR_factor_gt          0.1154
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_restrained_S_all      1.155
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.043

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
N1 N 0.7123(3) 0.50714(9) 0.20997(13) 0.0291(4) Uani 1 1 d . . .
N2 N 0.4272(3) 0.54709(9) 0.35605(14) 0.0302(4) Uani 1 1 d . . .
N3 N 0.7693(4) 0.47157(12) 0.40039(16) 0.0389(5) Uani 1 1 d . . .
H31 H 0.715(5) 0.4663(14) 0.475(2) 0.047(7) Uiso 1 1 d . . .
H32 H 0.909(5) 0.4480(15) 0.371(2) 0.052(7) Uiso 1 1 d . . .
C1 C 0.6336(4) 0.50898(11) 0.32078(16) 0.0278(4) Uani 1 1 d . . .
C2 C 0.2959(4) 0.58417(12) 0.27524(18) 0.0333(5) Uani 1 1 d . . .
H2A H 0.1481 0.6104 0.2973 0.040 Uiso 1 1 calc R . .
C3 C 0.3632(4) 0.58668(13) 0.16007(19) 0.0366(5) Uani 1 1 d . . .
H3A H 0.2673 0.6141 0.1036 0.044 Uiso 1 1 calc R . .
C4 C 0.5770(4) 0.54710(12) 0.13282(17) 0.0323(5) Uani 1 1 d . . .
H4A H 0.6311 0.5483 0.0551 0.039 Uiso 1 1 calc R . .
O11 O 0.1810(3) 0.38678(8) 0.29751(11) 0.0343(4) Uani 1 1 d . . .
O12 O 0.0412(3) 0.40903(8) 0.11734(12) 0.0351(4) Uani 1 1 d . . .
H12 H -0.073(6) 0.4412(18) 0.148(3) 0.066(9) Uiso 1 1 d . . .
C11 C 0.3558(3) 0.31390(11) 0.14493(17) 0.0272(4) Uani 1 1 d . . .
C12 C 0.3240(4) 0.28588(12) 0.03333(17) 0.0326(5) Uani 1 1 d . . .
H12A H 0.1905 0.3045 -0.0143 0.039 Uiso 1 1 calc R . .
C13 C 0.4873(4) 0.23076(12) -0.00844(19) 0.0371(5) Uani 1 1 d . . .
H13A H 0.4645 0.2111 -0.0846 0.045 Uiso 1 1 calc R . .
C14 C 0.6838(4) 0.20411(12) 0.06024(19) 0.0358(5) Uani 1 1 d . . .
H14A H 0.7972 0.1670 0.0308 0.043 Uiso 1 1 calc R . .
C15 C 0.7146(4) 0.23162(12) 0.17179(19) 0.0372(5) Uani 1 1 d . . .
H15A H 0.8484 0.2130 0.2192 0.045 Uiso 1 1 calc R . .
C16 C 0.5509(4) 0.28625(12) 0.21445(18) 0.0335(5) Uani 1 1 d . . .
H16A H 0.5717 0.3049 0.2912 0.040 Uiso 1 1 calc R . .
C17 C 0.1848(3) 0.37326(11) 0.19421(16) 0.0272(4) 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
N1 C4 1.332(3) . ?
N1 C1 1.357(2) . ?
N2 C2 1.325(3) . ?
N2 C1 1.354(2) . ?
N3 C1 1.330(3) . ?
N3 H31 0.92(3) . ?
N3 H32 0.92(3) . ?
C2 C3 1.387(3) . ?
C2 H2A 0.950 . ?
C3 C4 1.373(3) . ?
C3 H3A 0.950 . ?
C4 H4A 0.950 . ?
O11 C17 1.219(2) . ?
O12 C17 1.319(2) . ?
O12 H12 0.91(3) . ?
C11 C12 1.387(3) . ?
C11 C16 1.391(3) . ?
C11 C17 1.494(3) . ?
C12 C13 1.385(3) . ?
C12 H12A 0.950 . ?
C13 C14 1.385(3) . ?
C13 H13A 0.950 . ?
C14 C15 1.383(3) . ?
C14 H14A 0.950 . ?
C15 C16 1.384(3) . ?
C15 H15A 0.950 . ?
C16 H16A 0.950 . ?

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
C4 N1 C1 116.61(17) . . ?
C2 N2 C1 116.53(17) . . ?
C1 N3 H31 121.5(16) . . ?
C1 N3 H32 113.3(16) . . ?
H31 N3 H32 125(2) . . ?
N3 C1 N2 117.69(18) . . ?
N3 C1 N1 117.99(18) . . ?
N2 C1 N1 124.31(18) . . ?
N2 C2 C3 123.42(19) . . ?
N2 C2 H2A 118.3 . . ?
C3 C2 H2A 118.3 . . ?
C4 C3 C2 115.83(19) . . ?
C4 C3 H3A 122.1 . . ?
C2 C3 H3A 122.1 . . ?
N1 C4 C3 123.27(19) . . ?
N1 C4 H4A 118.4 . . ?
C3 C4 H4A 118.4 . . ?
C17 O12 H12 114.2(18) . . ?
C12 C11 C16 119.84(18) . . ?
C12 C11 C17 121.94(18) . . ?
C16 C11 C17 118.21(17) . . ?
C13 C12 C11 119.81(19) . . ?
C13 C12 H12A 120.1 . . ?
C11 C12 H12A 120.1 . . ?
C12 C13 C14 120.3(2) . . ?
C12 C13 H13A 119.8 . . ?
C14 C13 H13A 119.8 . . ?
C15 C14 C13 119.93(19) . . ?
C15 C14 H14A 120.0 . . ?
C13 C14 H14A 120.0 . . ?
C14 C15 C16 120.1(2) . . ?
C14 C15 H15A 120.0 . . ?
C16 C15 H15A 120.0 . . ?
C15 C16 C11 120.03(19) . . ?
C15 C16 H16A 120.0 . . ?
C11 C16 H16A 120.0 . . ?
O11 C17 O12 123.57(18) . . ?
O11 C17 C11 121.78(18) . . ?
O12 C17 C11 114.65(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N2 C1 N3 179.70(19) . . . . ?
C2 N2 C1 N1 0.4(3) . . . . ?
C4 N1 C1 N3 -177.99(19) . . . . ?
C4 N1 C1 N2 1.3(3) . . . . ?
C1 N2 C2 C3 -1.4(3) . . . . ?
N2 C2 C3 C4 0.7(3) . . . . ?
C1 N1 C4 C3 -2.1(3) . . . . ?
C2 C3 C4 N1 1.2(3) . . . . ?
C16 C11 C12 C13 -0.3(3) . . . . ?
C17 C11 C12 C13 -179.91(19) . . . . ?
C11 C12 C13 C14 -0.7(3) . . . . ?
C12 C13 C14 C15 1.1(3) . . . . ?
C13 C14 C15 C16 -0.6(3) . . . . ?
C14 C15 C16 C11 -0.4(3) . . . . ?
C12 C11 C16 C15 0.8(3) . . . . ?
C17 C11 C16 C15 -179.54(18) . . . . ?
C12 C11 C17 O11 165.38(19) . . . . ?
C16 C11 C17 O11 -14.3(3) . . . . ?
C12 C11 C17 O12 -14.7(3) . . . . ?
C16 C11 C17 O12 165.69(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O12 H12 N1 0.91(3) 1.77(3) 2.679(2) 178(3) 1_455
N3 H32 O11 0.92(3) 2.00(3) 2.916(2) 172(2) 1_655
N3 H31 N2 0.92(3) 2.12(3) 3.043(2) 177(2) 3_666

#=============================================================================

data_5
_database_code_depnum_ccdc_archive 'CCDC 692782'

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H14 N2 2+, 2(C7 H5 O3 -)'
_chemical_formula_sum            'C20 H24 N2 O6'
_chemical_formula_weight         388.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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           orthorhombic
_symmetry_space_group_name_H-M   'P c c n'
_symmetry_space_group_name_Hall  '-P 2ab 2ac'

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

_cell_length_a                   17.7236(6)
_cell_length_b                   22.0059(7)
_cell_length_c                   9.8501(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3841.8(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    5405
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      24.17

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1648
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.885
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   
;
SADABS v.2.10 (Sheldrick, 2003)
Ratio of minimum to maximum apparent transmission: 0.888902
;

_exptl_special_details           
;
One peak in the residual electron density (ca 0.8 e Å⁻³) is
located in an appropriate position for an O atom bound to C16.
Thus, there is a suggestion of minimal disorder for one salicylic
acid molecule, corresponding to 2-fold rotation about the
C11...C14 axis. This residual peak is small, and disorder was
therefore not modelled.
;

_diffrn_ambient_temperature      180(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-Nonius X8APEX-II CCD'
_diffrn_measurement_method       'thin-slice ω and φ scans'
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            34870
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_sigmaI/netI    0.0173
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.57
_diffrn_reflns_theta_max         25.25
_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.986
_reflns_number_total             3422
_reflns_number_gt                2772
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 v.1.0-22 (Bruker Nonius, 2004)'
_computing_cell_refinement       'SAINT v.7.06a (Bruker, 2003)'
_computing_data_reduction        'SAINT v.7.06a'
_computing_structure_solution    'SHELXTL v.6.10 (Sheldrick, 2000)'
_computing_structure_refinement  'SHELXTL v.6.10'
_computing_molecular_graphics    'SHELXTL v.6.10'
_computing_publication_material  'SHELXTL v.6.10'

_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)+(0.0644P)²+2.4477P] 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         3422
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1273
_refine_ls_wR_factor_gt          0.1166
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.806
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.043

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
O11 O 0.60989(8) 0.44345(6) 0.40931(14) 0.0360(3) Uani 1 1 d . . .
O12 O 0.57038(8) 0.34871(6) 0.44071(13) 0.0370(3) Uani 1 1 d . . .
O13 O 0.59035(9) 0.26888(6) 0.26113(15) 0.0448(4) Uani 1 1 d . . .
H13 H 0.5731 0.2846 0.3324 0.067 Uiso 1 1 calc R . .
C11 C 0.64265(9) 0.36907(8) 0.24475(18) 0.0253(4) Uani 1 1 d . . .
C12 C 0.63200(10) 0.31016(8) 0.19406(19) 0.0289(4) Uani 1 1 d . . .
C13 C 0.66541(11) 0.29267(9) 0.0726(2) 0.0369(5) Uani 1 1 d . . .
H13A H 0.6568 0.2531 0.0372 0.044 Uiso 1 1 calc R . .
C14 C 0.71106(12) 0.33288(10) 0.0035(2) 0.0425(5) Uani 1 1 d . . .
H14A H 0.7340 0.3207 -0.0793 0.051 Uiso 1 1 calc R . .
C15 C 0.72398(11) 0.39093(10) 0.0532(2) 0.0420(5) Uani 1 1 d . . .
H15A H 0.7559 0.4182 0.0053 0.050 Uiso 1 1 calc R . .
C16 C 0.68992(10) 0.40870(9) 0.1731(2) 0.0330(4) Uani 1 1 d . . .
H16A H 0.6987 0.4484 0.2075 0.040 Uiso 1 1 calc R . .
C17 C 0.60584(10) 0.39012(8) 0.37251(18) 0.0266(4) Uani 1 1 d . . .
O21 O 0.45271(9) 0.35307(7) 1.15951(15) 0.0506(4) Uani 1 1 d . . .
O22 O 0.40799(8) 0.44590(6) 1.13404(14) 0.0405(4) Uani 1 1 d . . .
O23 O 0.40077(11) 0.28256(7) 1.3320(2) 0.0618(5) Uani 1 1 d . . .
H23 H 0.4222 0.2929 1.2596 0.093 Uiso 1 1 calc R . .
C21 C 0.36284(10) 0.38687(8) 1.32003(18) 0.0286(4) Uani 1 1 d . . .
C22 C 0.35889(11) 0.32906(9) 1.3787(2) 0.0367(5) Uani 1 1 d . . .
C23 C 0.31120(13) 0.31880(11) 1.4880(2) 0.0503(6) Uani 1 1 d . . .
H23A H 0.3081 0.2795 1.5275 0.060 Uiso 1 1 calc R . .
C24 C 0.26829(12) 0.36569(13) 1.5393(2) 0.0570(7) Uani 1 1 d . . .
H24A H 0.2358 0.3585 1.6142 0.068 Uiso 1 1 calc R . .
C25 C 0.27198(13) 0.42318(12) 1.4828(3) 0.0542(6) Uani 1 1 d . . .
H25A H 0.2426 0.4554 1.5190 0.065 Uiso 1 1 calc R . .
C26 C 0.31877(11) 0.43312(10) 1.3736(2) 0.0406(5) Uani 1 1 d . . .
H26A H 0.3209 0.4725 1.3340 0.049 Uiso 1 1 calc R . .
C27 C 0.41170(11) 0.39633(9) 1.19725(19) 0.0329(4) Uani 1 1 d . . .
N1 N 0.46369(9) 0.41368(7) 0.89136(15) 0.0277(4) Uani 1 1 d . . .
H1A H 0.4434 0.4240 0.9753 0.033 Uiso 1 1 calc R . .
N2 N 0.51830(9) 0.38607(6) 0.66637(15) 0.0285(4) Uani 1 1 d . . .
H2A H 0.5384 0.3757 0.5823 0.034 Uiso 1 1 calc R . .
C31 C 0.44211(12) 0.46095(9) 0.78965(19) 0.0347(5) Uani 1 1 d . . .
H31A H 0.4594 0.5014 0.8206 0.042 Uiso 1 1 calc R . .
H31B H 0.3866 0.4621 0.7795 0.042 Uiso 1 1 calc R . .
C32 C 0.47861(14) 0.44537(9) 0.6547(2) 0.0410(5) Uani 1 1 d . . .
H32A H 0.4396 0.4429 0.5830 0.049 Uiso 1 1 calc R . .
H32B H 0.5150 0.4775 0.6292 0.049 Uiso 1 1 calc R . .
C33 C 0.46449(12) 0.33823(9) 0.7097(2) 0.0375(5) Uani 1 1 d . . .
H33A H 0.4905 0.2984 0.7126 0.045 Uiso 1 1 calc R . .
H33B H 0.4226 0.3354 0.6435 0.045 Uiso 1 1 calc R . .
C34 C 0.43347(13) 0.35344(9) 0.8490(2) 0.0396(5) Uani 1 1 d . . .
H34A H 0.3777 0.3548 0.8459 0.048 Uiso 1 1 calc R . .
H34B H 0.4488 0.3219 0.9151 0.048 Uiso 1 1 calc R . .
C35 C 0.54756(10) 0.41040(9) 0.90316(19) 0.0318(4) Uani 1 1 d . . .
H35A H 0.5618 0.3809 0.9746 0.038 Uiso 1 1 calc R . .
H35B H 0.5680 0.4507 0.9285 0.038 Uiso 1 1 calc R . .
C36 C 0.58007(11) 0.39047(9) 0.7667(2) 0.0357(5) Uani 1 1 d . . .
H36A H 0.6181 0.4203 0.7354 0.043 Uiso 1 1 calc R . .
H36B H 0.6052 0.3505 0.7764 0.043 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O11 C17 1.230(2) . ?
O12 C17 1.295(2) . ?
O13 C12 1.344(2) . ?
O13 H13 0.840 . ?
C11 C16 1.400(3) . ?
C11 C12 1.402(3) . ?
C11 C17 1.491(3) . ?
C12 C13 1.390(3) . ?
C13 C14 1.378(3) . ?
C13 H13A 0.950 . ?
C14 C15 1.387(3) . ?
C14 H14A 0.950 . ?
C15 C16 1.383(3) . ?
C15 H15A 0.950 . ?
C16 H16A 0.950 . ?
O21 C27 1.254(2) . ?
O22 C27 1.258(2) . ?
O23 C22 1.345(2) . ?
O23 H23 0.840 . ?
C21 C26 1.387(3) . ?
C21 C22 1.399(3) . ?
C21 C27 1.502(3) . ?
C22 C23 1.388(3) . ?
C23 C24 1.378(3) . ?
C23 H23A 0.950 . ?
C24 C25 1.383(4) . ?
C24 H24A 0.950 . ?
C25 C26 1.376(3) . ?
C25 H25A 0.950 . ?
C26 H26A 0.950 . ?
N1 C34 1.489(2) . ?
N1 C35 1.493(2) . ?
N1 C31 1.494(2) . ?
N1 H1A 0.930 . ?
N2 C36 1.478(2) . ?
N2 C33 1.483(2) . ?
N2 C32 1.487(2) . ?
N2 H2A 0.930 . ?
C31 C32 1.518(3) . ?
C31 H31A 0.990 . ?
C31 H31B 0.990 . ?
C32 H32A 0.990 . ?
C32 H32B 0.990 . ?
C33 C34 1.516(3) . ?
C33 H33A 0.990 . ?
C33 H33B 0.990 . ?
C34 H34A 0.990 . ?
C34 H34B 0.990 . ?
C35 C36 1.527(3) . ?
C35 H35A 0.990 . ?
C35 H35B 0.990 . ?
C36 H36A 0.990 . ?
C36 H36B 0.990 . ?

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
C12 O13 H13 109.5 . . ?
C16 C11 C12 118.50(17) . . ?
C16 C11 C17 119.57(16) . . ?
C12 C11 C17 121.93(16) . . ?
O13 C12 C13 118.05(17) . . ?
O13 C12 C11 121.59(16) . . ?
C13 C12 C11 120.36(17) . . ?
C14 C13 C12 119.82(19) . . ?
C14 C13 H13A 120.1 . . ?
C12 C13 H13A 120.1 . . ?
C13 C14 C15 120.94(19) . . ?
C13 C14 H14A 119.5 . . ?
C15 C14 H14A 119.5 . . ?
C16 C15 C14 119.31(19) . . ?
C16 C15 H15A 120.3 . . ?
C14 C15 H15A 120.3 . . ?
C15 C16 C11 121.03(19) . . ?
C15 C16 H16A 119.5 . . ?
C11 C16 H16A 119.5 . . ?
O11 C17 O12 123.14(17) . . ?
O11 C17 C11 121.30(16) . . ?
O12 C17 C11 115.57(15) . . ?
C22 O23 H23 109.5 . . ?
C26 C21 C22 118.82(18) . . ?
C26 C21 C27 121.94(18) . . ?
C22 C21 C27 119.17(17) . . ?
O23 C22 C23 118.54(19) . . ?
O23 C22 C21 121.53(18) . . ?
C23 C22 C21 119.93(19) . . ?
C24 C23 C22 119.9(2) . . ?
C24 C23 H23A 120.0 . . ?
C22 C23 H23A 120.0 . . ?
C23 C24 C25 120.8(2) . . ?
C23 C24 H24A 119.6 . . ?
C25 C24 H24A 119.6 . . ?
C26 C25 C24 119.2(2) . . ?
C26 C25 H25A 120.4 . . ?
C24 C25 H25A 120.4 . . ?
C25 C26 C21 121.3(2) . . ?
C25 C26 H26A 119.3 . . ?
C21 C26 H26A 119.3 . . ?
O21 C27 O22 122.81(18) . . ?
O21 C27 C21 117.89(17) . . ?
O22 C27 C21 119.25(18) . . ?
C34 N1 C35 109.68(15) . . ?
C34 N1 C31 109.86(15) . . ?
C35 N1 C31 109.93(14) . . ?
C34 N1 H1A 109.1 . . ?
C35 N1 H1A 109.1 . . ?
C31 N1 H1A 109.1 . . ?
C36 N2 C33 109.31(15) . . ?
C36 N2 C32 110.17(15) . . ?
C33 N2 C32 109.94(16) . . ?
C36 N2 H2A 109.1 . . ?
C33 N2 H2A 109.1 . . ?
C32 N2 H2A 109.1 . . ?
N1 C31 C32 108.73(14) . . ?
N1 C31 H31A 109.9 . . ?
C32 C31 H31A 109.9 . . ?
N1 C31 H31B 109.9 . . ?
C32 C31 H31B 109.9 . . ?
H31A C31 H31B 108.3 . . ?
N2 C32 C31 109.39(15) . . ?
N2 C32 H32A 109.8 . . ?
C31 C32 H32A 109.8 . . ?
N2 C32 H32B 109.8 . . ?
C31 C32 H32B 109.8 . . ?
H32A C32 H32B 108.2 . . ?
N2 C33 C34 109.68(15) . . ?
N2 C33 H33A 109.7 . . ?
C34 C33 H33A 109.7 . . ?
N2 C33 H33B 109.7 . . ?
C34 C33 H33B 109.7 . . ?
H33A C33 H33B 108.2 . . ?
N1 C34 C33 108.65(15) . . ?
N1 C34 H34A 110.0 . . ?
C33 C34 H34A 110.0 . . ?
N1 C34 H34B 110.0 . . ?
C33 C34 H34B 110.0 . . ?
H34A C34 H34B 108.3 . . ?
N1 C35 C36 108.73(15) . . ?
N1 C35 H35A 109.9 . . ?
C36 C35 H35A 109.9 . . ?
N1 C35 H35B 109.9 . . ?
C36 C35 H35B 109.9 . . ?
H35A C35 H35B 108.3 . . ?
N2 C36 C35 109.14(15) . . ?
N2 C36 H36A 109.9 . . ?
C35 C36 H36A 109.9 . . ?
N2 C36 H36B 109.9 . . ?
C35 C36 H36B 109.9 . . ?
H36A C36 H36B 108.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 C11 C12 O13 176.71(17) . . . . ?
C17 C11 C12 O13 -2.7(3) . . . . ?
C16 C11 C12 C13 -2.5(3) . . . . ?
C17 C11 C12 C13 178.10(16) . . . . ?
O13 C12 C13 C14 -177.36(18) . . . . ?
C11 C12 C13 C14 1.9(3) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C13 C14 C15 C16 -0.6(3) . . . . ?
C14 C15 C16 C11 -0.1(3) . . . . ?
C12 C11 C16 C15 1.6(3) . . . . ?
C17 C11 C16 C15 -178.98(17) . . . . ?
C16 C11 C17 O11 7.5(3) . . . . ?
C12 C11 C17 O11 -173.15(17) . . . . ?
C16 C11 C17 O12 -172.16(16) . . . . ?
C12 C11 C17 O12 7.2(2) . . . . ?
C26 C21 C22 O23 -179.40(19) . . . . ?
C27 C21 C22 O23 3.5(3) . . . . ?
C26 C21 C22 C23 0.3(3) . . . . ?
C27 C21 C22 C23 -176.85(19) . . . . ?
O23 C22 C23 C24 179.2(2) . . . . ?
C21 C22 C23 C24 -0.5(3) . . . . ?
C22 C23 C24 C25 0.1(4) . . . . ?
C23 C24 C25 C26 0.5(4) . . . . ?
C24 C25 C26 C21 -0.7(3) . . . . ?
C22 C21 C26 C25 0.3(3) . . . . ?
C27 C21 C26 C25 177.37(19) . . . . ?
C26 C21 C27 O21 176.44(19) . . . . ?
C22 C21 C27 O21 -6.5(3) . . . . ?
C26 C21 C27 O22 -6.1(3) . . . . ?
C22 C21 C27 O22 170.94(18) . . . . ?
C34 N1 C31 C32 -63.1(2) . . . . ?
C35 N1 C31 C32 57.6(2) . . . . ?
C36 N2 C32 C31 -63.2(2) . . . . ?
C33 N2 C32 C31 57.3(2) . . . . ?
N1 C31 C32 N2 4.4(2) . . . . ?
C36 N2 C33 C34 58.6(2) . . . . ?
C32 N2 C33 C34 -62.4(2) . . . . ?
C35 N1 C34 C33 -62.7(2) . . . . ?
C31 N1 C34 C33 58.2(2) . . . . ?
N2 C33 C34 N1 3.8(2) . . . . ?
C34 N1 C35 C36 57.83(19) . . . . ?
C31 N1 C35 C36 -63.06(19) . . . . ?
C33 N2 C36 C35 -63.32(19) . . . . ?
C32 N2 C36 C35 57.6(2) . . . . ?
N1 C35 C36 N2 4.6(2) . . . . ?

#=============================================================================

data_6
_database_code_depnum_ccdc_archive 'CCDC 692783'

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H8 N2, 2(C7 H6 O3)'
_chemical_formula_sum            'C26 H20 N2 O6'
_chemical_formula_weight         456.44

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   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   13.0229(13)
_cell_length_b                   3.8561(3)
_cell_length_c                   22.048(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.322(4)
_cell_angle_gamma                90.00
_cell_volume                     1072.79(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    4849
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      24.69

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             476
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   
;
SADABS v.2.10 (Sheldrick, 2003)
Ratio of minimum to maximum apparent transmission: 0.895081
;

_exptl_special_details           ?

_diffrn_ambient_temperature      180(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-Nonius X8APEX-II CCD'
_diffrn_measurement_method       'thin-slice ω and φ scans'
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14159
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0230
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.76
_diffrn_reflns_theta_max         25.05
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.995
_reflns_number_total             1898
_reflns_number_gt                1525
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 v.1.0-22 (Bruker Nonius, 2004)'
_computing_cell_refinement       'SAINT v.7.06a (Bruker, 2003)'
_computing_data_reduction        'SAINT v.7.06a'
_computing_structure_solution    'SHELXTL v.6.10 (Sheldrick, 2000)'
_computing_structure_refinement  'SHELXTL v.6.10'
_computing_molecular_graphics    'SHELXTL v.6.10'
_computing_publication_material  'SHELXTL v.6.10'

_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)+(0.0472P)²+0.2121P] 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         1898
_refine_ls_number_parameters     159
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0882
_refine_ls_wR_factor_gt          0.0816
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.034

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.68146(7) 0.3622(3) 0.33730(4) 0.0374(3) Uani 1 1 d . . .
O2 O 0.75261(8) 0.3905(3) 0.44023(4) 0.0373(3) Uani 1 1 d . . .
H2 H 0.6910(16) 0.277(6) 0.4452(9) 0.083(7) Uiso 1 1 d . . .
O3 O 0.78216(8) 0.6400(3) 0.26136(4) 0.0425(3) Uani 1 1 d . . .
H3 H 0.7310 0.5440 0.2716 0.064 Uiso 1 1 calc R . .
C1 C 0.85061(10) 0.6230(3) 0.37353(6) 0.0246(3) Uani 1 1 d . . .
C2 C 0.85937(10) 0.7103(4) 0.31335(6) 0.0278(3) Uani 1 1 d . . .
C3 C 0.95047(11) 0.8736(3) 0.30576(7) 0.0329(4) Uani 1 1 d . . .
H3A H 0.9558 0.9384 0.2651 0.039 Uiso 1 1 calc R . .
C4 C 1.03268(11) 0.9417(4) 0.35662(7) 0.0355(4) Uani 1 1 d . . .
H4A H 1.0951 1.0497 0.3508 0.043 Uiso 1 1 calc R . .
C5 C 1.02573(11) 0.8546(4) 0.41659(7) 0.0342(4) Uani 1 1 d . . .
H5A H 1.0831 0.9010 0.4516 0.041 Uiso 1 1 calc R . .
C6 C 0.93479(10) 0.7003(4) 0.42466(6) 0.0289(3) Uani 1 1 d . . .
H6A H 0.9292 0.6453 0.4657 0.035 Uiso 1 1 calc R . .
C7 C 0.75437(10) 0.4484(4) 0.38146(6) 0.0270(3) Uani 1 1 d . . .
N1 N 0.58265(8) 0.1065(3) 0.47325(5) 0.0244(3) Uani 1 1 d . . .
C8 C 0.40415(11) -0.3014(4) 0.34011(6) 0.0307(3) Uani 1 1 d . . .
H8A H 0.4001 -0.3513 0.2974 0.037 Uiso 1 1 calc R . .
C9 C 0.48998(10) -0.1339(3) 0.37467(6) 0.0275(3) Uani 1 1 d . . .
H9A H 0.5453 -0.0652 0.3561 0.033 Uiso 1 1 calc R . .
C10 C 0.49736(9) -0.0607(3) 0.43875(6) 0.0234(3) Uani 1 1 d . . .
C11 C 0.58696(9) 0.1680(3) 0.53396(6) 0.0234(3) Uani 1 1 d . . .
C12 C 0.67581(10) 0.3413(3) 0.57229(6) 0.0287(3) Uani 1 1 d . . .
H12A H 0.7324 0.4136 0.5551 0.034 Uiso 1 1 calc R . .
C13 C 0.68019(11) 0.4041(4) 0.63351(6) 0.0316(3) Uani 1 1 d . . .
H13A H 0.7403 0.5180 0.6589 0.038 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.2258(15) . ?
O2 C7 1.3207(15) . ?
O2 H2 0.94(2) . ?
O3 C2 1.3521(16) . ?
O3 H3 0.840 . ?
C1 C6 1.3963(18) . ?
C1 C2 1.4006(18) . ?
C1 C7 1.4708(18) . ?
C2 C3 1.3892(19) . ?
C3 C4 1.3707(19) . ?
C3 H3A 0.950 . ?
C4 C5 1.389(2) . ?
C4 H4A 0.950 . ?
C5 C6 1.3757(19) . ?
C5 H5A 0.950 . ?
C6 H6A 0.950 . ?
N1 C10 1.3453(16) . ?
N1 C11 1.3469(16) . ?
C8 C9 1.3511(19) . ?
C8 C13 1.421(2) 3_656 ?
C8 H8A 0.950 . ?
C9 C10 1.4205(18) . ?
C9 H9A 0.950 . ?
C10 C11 1.4373(18) 3_656 ?
C11 C12 1.4197(18) . ?
C12 C13 1.3585(18) . ?
C12 H12A 0.950 . ?
C13 H13A 0.950 . ?

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
C7 O2 H2 114.4(12) . . ?
C2 O3 H3 109.5 . . ?
C6 C1 C2 118.80(12) . . ?
C6 C1 C7 121.58(11) . . ?
C2 C1 C7 119.61(12) . . ?
O3 C2 C3 117.82(12) . . ?
O3 C2 C1 122.49(12) . . ?
C3 C2 C1 119.68(12) . . ?
C4 C3 C2 120.38(13) . . ?
C4 C3 H3A 119.8 . . ?
C2 C3 H3A 119.8 . . ?
C3 C4 C5 120.73(13) . . ?
C3 C4 H4A 119.6 . . ?
C5 C4 H4A 119.6 . . ?
C6 C5 C4 119.26(13) . . ?
C6 C5 H5A 120.4 . . ?
C4 C5 H5A 120.4 . . ?
C5 C6 C1 121.13(12) . . ?
C5 C6 H6A 119.4 . . ?
C1 C6 H6A 119.4 . . ?
O1 C7 O2 122.38(12) . . ?
O1 C7 C1 123.04(11) . . ?
O2 C7 C1 114.58(11) . . ?
C10 N1 C11 118.16(11) . . ?
C9 C8 C13 121.19(12) . 3_656 ?
C9 C8 H8A 119.4 . . ?
C13 C8 H8A 119.4 3_656 . ?
C8 C9 C10 119.93(12) . . ?
C8 C9 H9A 120.0 . . ?
C10 C9 H9A 120.0 . . ?
N1 C10 C9 120.05(11) . . ?
N1 C10 C11 120.72(11) . 3_656 ?
C9 C10 C11 119.24(12) . 3_656 ?
N1 C11 C12 120.14(11) . . ?
N1 C11 C10 121.12(11) . 3_656 ?
C12 C11 C10 118.74(11) . 3_656 ?
C13 C12 C11 120.20(12) . . ?
C13 C12 H12A 119.9 . . ?
C11 C12 H12A 119.9 . . ?
C12 C13 C8 120.69(13) . 3_656 ?
C12 C13 H13A 119.7 . . ?
C8 C13 H13A 119.7 3_656 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 O3 179.04(12) . . . . ?
C7 C1 C2 O3 0.0(2) . . . . ?
C6 C1 C2 C3 -0.57(19) . . . . ?
C7 C1 C2 C3 -179.65(12) . . . . ?
O3 C2 C3 C4 -178.01(13) . . . . ?
C1 C2 C3 C4 1.6(2) . . . . ?
C2 C3 C4 C5 -1.1(2) . . . . ?
C3 C4 C5 C6 -0.4(2) . . . . ?
C4 C5 C6 C1 1.5(2) . . . . ?
C2 C1 C6 C5 -1.0(2) . . . . ?
C7 C1 C6 C5 178.10(12) . . . . ?
C6 C1 C7 O1 -176.35(13) . . . . ?
C2 C1 C7 O1 2.7(2) . . . . ?
C6 C1 C7 O2 3.52(18) . . . . ?
C2 C1 C7 O2 -177.42(12) . . . . ?
C13 C8 C9 C10 0.6(2) 3_656 . . . ?
C11 N1 C10 C9 -179.43(11) . . . . ?
C11 N1 C10 C11 0.42(19) . . . 3_656 ?
C8 C9 C10 N1 -179.89(12) . . . . ?
C8 C9 C10 C11 0.26(19) . . . 3_656 ?
C10 N1 C11 C12 179.52(11) . . . . ?
C10 N1 C11 C10 -0.42(19) . . . 3_656 ?
N1 C11 C12 C13 179.90(12) . . . . ?
C10 C11 C12 C13 -0.16(19) 3_656 . . . ?
C11 C12 C13 C8 -0.7(2) . . . 3_656 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 N1 0.94(2) 1.80(2) 2.7250(14) 166.1(18) .

#=============================================================================

data_7a
_database_code_depnum_ccdc_archive 'CCDC 692784'

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H14 N2 O2, 2(C7 H6 O3)'
_chemical_formula_sum            'C22 H26 N2 O8'
_chemical_formula_weight         446.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

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

_cell_length_a                   11.590(3)
_cell_length_b                   13.283(3)
_cell_length_c                   13.730(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2113.7(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    1160
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      18.88

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.784
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_process_details   
;
SADABS v.2.10 (Sheldrick, 2003)
Ratio of minimum to maximum apparent transmission: 0.786003
;

_exptl_special_details           
;
Data truncated to 0.90Å
;

_diffrn_ambient_temperature      180(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-Nonius X8APEX-II CCD'
_diffrn_measurement_method       'thin-slice ω and φ scans'
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25716
_diffrn_reflns_av_R_equivalents  0.1090
_diffrn_reflns_av_sigmaI/netI    0.0648
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.52
_diffrn_reflns_theta_max         23.25
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        23.25
_diffrn_measured_fraction_theta_full 0.997
_reflns_number_total             1513
_reflns_number_gt                1025
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 v.1.0-22 (Bruker Nonius, 2004)'
_computing_cell_refinement       'SAINT v.7.06a (Bruker, 2003)'
_computing_data_reduction        'SAINT v.7.06a'
_computing_structure_solution    'SHELXTL v.6.10 (Sheldrick, 2000)'
_computing_structure_refinement  'SHELXTL v.6.10'
_computing_molecular_graphics    'SHELXTL v.6.10'
_computing_publication_material  'SHELXTL v.6.10'

_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)+(0.0365P)²+0.2453P] 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     SHELXL
_refine_ls_extinction_coef       0.0038(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1513
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0395
_refine_ls_wR_factor_ref         0.0963
_refine_ls_wR_factor_gt          0.0852
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.047

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.44930(13) 0.57337(12) 0.41250(12) 0.0305(5) Uani 1 1 d . . .
H1 H 0.481(3) 0.547(2) 0.343(2) 0.095(11) Uiso 1 1 d . . .
O2 O 0.62941(14) 0.62941(12) 0.43705(11) 0.0360(5) Uani 1 1 d . . .
O3 O 0.67607(14) 0.72358(13) 0.59909(14) 0.0384(5) Uani 1 1 d . . .
H3 H 0.686(2) 0.696(2) 0.541(2) 0.061(10) Uiso 1 1 d . . .
C11 C 0.48368(19) 0.67071(17) 0.55277(16) 0.0233(6) Uani 1 1 d . . .
C12 C 0.56078(19) 0.71671(16) 0.61796(16) 0.0259(6) Uani 1 1 d . . .
C13 C 0.5200(2) 0.75802(16) 0.70438(17) 0.0290(6) Uani 1 1 d . . .
H13A H 0.5721 0.7886 0.7489 0.035 Uiso 1 1 calc R . .
C14 C 0.4038(2) 0.75458(17) 0.72539(18) 0.0330(7) Uani 1 1 d . . .
H14A H 0.3763 0.7826 0.7846 0.040 Uiso 1 1 calc R . .
C15 C 0.3267(2) 0.71070(18) 0.66119(18) 0.0331(7) Uani 1 1 d . . .
H15A H 0.2466 0.7097 0.6758 0.040 Uiso 1 1 calc R . .
C16 C 0.3667(2) 0.66856(17) 0.57621(17) 0.0307(6) Uani 1 1 d . . .
H16A H 0.3138 0.6375 0.5328 0.037 Uiso 1 1 calc R . .
C17 C 0.5278(2) 0.62332(17) 0.46279(16) 0.0264(6) Uani 1 1 d . . .
O4 O 0.49106(14) 0.49415(11) 0.24853(11) 0.0295(5) Uani 1 1 d . . .
N1 N 0.53941(15) 0.46893(14) 0.09246(13) 0.0276(5) Uani 1 1 d . . .
C21 C 0.61861(19) 0.46910(18) 0.00926(15) 0.0304(6) Uani 1 1 d . . .
H21A H 0.6191 0.4018 -0.0217 0.036 Uiso 1 1 calc R . .
H21B H 0.6979 0.4841 0.0319 0.036 Uiso 1 1 calc R . .
C22 C 0.41897(19) 0.45209(18) 0.06468(16) 0.0303(6) Uani 1 1 d . . .
H22A H 0.3692 0.4561 0.1231 0.036 Uiso 1 1 calc R . .
H22B H 0.4105 0.3840 0.0362 0.036 Uiso 1 1 calc R . .
C23 C 0.5673(2) 0.49226(16) 0.18487(17) 0.0250(6) Uani 1 1 d . . .
C24 C 0.6912(2) 0.51673(19) 0.20831(17) 0.0332(7) Uani 1 1 d . . .
H24A H 0.6983 0.5319 0.2779 0.050 Uiso 1 1 calc R . .
H24B H 0.7157 0.5753 0.1701 0.050 Uiso 1 1 calc R . .
H24C H 0.7401 0.4589 0.1922 0.050 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C17 1.321(3) . ?
O1 H1 1.08(3) . ?
O2 C17 1.232(3) . ?
O3 C12 1.364(3) . ?
O3 H3 0.89(3) . ?
C11 C16 1.394(3) . ?
C11 C12 1.405(3) . ?
C11 C17 1.478(3) . ?
C12 C13 1.390(3) . ?
C13 C14 1.378(3) . ?
C13 H13A 0.950 . ?
C14 C15 1.384(3) . ?
C14 H14A 0.950 . ?
C15 C16 1.375(3) . ?
C15 H15A 0.950 . ?
C16 H16A 0.950 . ?
O4 C23 1.243(3) . ?
N1 C23 1.345(3) . ?
N1 C22 1.464(3) . ?
N1 C21 1.465(3) . ?
C21 C22 1.522(3) 5_665 ?
C21 H21A 0.990 . ?
C21 H21B 0.990 . ?
C22 C21 1.522(3) 5_665 ?
C22 H22A 0.990 . ?
C22 H22B 0.990 . ?
C23 C24 1.507(3) . ?
C24 H24A 0.980 . ?
C24 H24B 0.980 . ?
C24 H24C 0.980 . ?

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
C17 O1 H1 112.8(16) . . ?
C12 O3 H3 105.4(17) . . ?
C16 C11 C12 118.7(2) . . ?
C16 C11 C17 121.4(2) . . ?
C12 C11 C17 119.9(2) . . ?
O3 C12 C13 118.0(2) . . ?
O3 C12 C11 122.1(2) . . ?
C13 C12 C11 120.0(2) . . ?
C14 C13 C12 119.9(2) . . ?
C14 C13 H13A 120.1 . . ?
C12 C13 H13A 120.1 . . ?
C13 C14 C15 120.8(2) . . ?
C13 C14 H14A 119.6 . . ?
C15 C14 H14A 119.6 . . ?
C16 C15 C14 119.6(2) . . ?
C16 C15 H15A 120.2 . . ?
C14 C15 H15A 120.2 . . ?
C15 C16 C11 121.1(2) . . ?
C15 C16 H16A 119.5 . . ?
C11 C16 H16A 119.5 . . ?
O2 C17 O1 122.8(2) . . ?
O2 C17 C11 122.8(2) . . ?
O1 C17 C11 114.4(2) . . ?
C23 N1 C22 120.66(18) . . ?
C23 N1 C21 125.74(19) . . ?
C22 N1 C21 113.23(17) . . ?
N1 C21 C22 109.99(18) . 5_665 ?
N1 C21 H21A 109.7 . . ?
C22 C21 H21A 109.7 5_665 . ?
N1 C21 H21B 109.7 . . ?
C22 C21 H21B 109.7 5_665 . ?
H21A C21 H21B 108.2 . . ?
N1 C22 C21 109.97(18) . 5_665 ?
N1 C22 H22A 109.7 . . ?
C21 C22 H22A 109.7 5_665 . ?
N1 C22 H22B 109.7 . . ?
C21 C22 H22B 109.7 5_665 . ?
H22A C22 H22B 108.2 . . ?
O4 C23 N1 119.8(2) . . ?
O4 C23 C24 121.5(2) . . ?
N1 C23 C24 118.7(2) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 C11 C12 O3 -178.6(2) . . . . ?
C17 C11 C12 O3 3.1(3) . . . . ?
C16 C11 C12 C13 0.7(3) . . . . ?
C17 C11 C12 C13 -177.60(19) . . . . ?
O3 C12 C13 C14 178.7(2) . . . . ?
C11 C12 C13 C14 -0.6(3) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C13 C14 C15 C16 1.1(4) . . . . ?
C14 C15 C16 C11 -1.1(4) . . . . ?
C12 C11 C16 C15 0.2(3) . . . . ?
C17 C11 C16 C15 178.4(2) . . . . ?
C16 C11 C17 O2 175.3(2) . . . . ?
C12 C11 C17 O2 -6.5(3) . . . . ?
C16 C11 C17 O1 -5.1(3) . . . . ?
C12 C11 C17 O1 173.16(19) . . . . ?
C23 N1 C21 C22 -116.5(2) . . . 5_665 ?
C22 N1 C21 C22 56.5(3) . . . 5_665 ?
C23 N1 C22 C21 116.9(2) . . . 5_665 ?
C21 N1 C22 C21 -56.5(3) . . . 5_665 ?
C22 N1 C23 O4 4.0(3) . . . . ?
C21 N1 C23 O4 176.5(2) . . . . ?
C22 N1 C23 C24 -175.3(2) . . . . ?
C21 N1 C23 C24 -2.8(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O4 1.08(3) 1.48(3) 2.532(2) 163(3) .
O3 H3 O2 0.89(3) 1.80(3) 2.609(2) 151(2) .

#=============================================================================

data_7b
_database_code_depnum_ccdc_archive 'CCDC 692785'

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H14 N2 O2, 2(C7 H6 O3)'
_chemical_formula_sum            'C22 H26 N2 O8'
_chemical_formula_weight         446.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   7.5378(9)
_cell_length_b                   7.9689(8)
_cell_length_c                   9.6533(12)
_cell_angle_alpha                70.378(4)
_cell_angle_beta                 77.017(4)
_cell_angle_gamma                79.533(4)
_cell_volume                     528.64(11)
_cell_formula_units_Z            1
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    2571
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      22.58

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             236
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.800
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   
;
SADABS v.2.10 (Sheldrick, 2003)
Ratio of minimum to maximum apparent transmission: 0.809433
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      180(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-Nonius X8APEX-II CCD'
_diffrn_measurement_method       'thin-slice ω and φ scans'
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10156
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_sigmaI/netI    0.0540
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.55
_diffrn_reflns_theta_max         25.11
_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        25.11
_diffrn_measured_fraction_theta_full 0.978
_reflns_number_total             1838
_reflns_number_gt                1263
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 v.1.0-22 (Bruker Nonius, 2004)'
_computing_cell_refinement       'SAINT v.7.06a (Bruker, 2003)'
_computing_data_reduction        'SAINT v.7.06a'
_computing_structure_solution    'SHELXTL v.6.10 (Sheldrick, 2000)'
_computing_structure_refinement  'SHELXTL v.6.10'
_computing_molecular_graphics    'SHELXTL v.6.10'
_computing_publication_material  'SHELXTL v.6.10'

_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)+(0.0669P)²+0.2754P] 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         1838
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1584
_refine_ls_wR_factor_gt          0.1490
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_restrained_S_all      1.127
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.057

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3746(3) 0.6568(3) 0.3901(2) 0.0377(5) Uani 1 1 d . . .
H1 H 0.321(6) 0.540(6) 0.419(5) 0.091(14) Uiso 1 1 d . . .
O2 O 0.5830(3) 0.5545(3) 0.2225(2) 0.0465(6) Uani 1 1 d . . .
O3 O 0.7896(3) 0.7735(3) 0.0153(2) 0.0461(6) Uani 1 1 d . . .
H3 H 0.744(7) 0.675(6) 0.061(5) 0.102(17) Uiso 1 1 d . . .
C11 C 0.5737(4) 0.8573(3) 0.2141(3) 0.0283(6) Uani 1 1 d . . .
C12 C 0.7069(4) 0.8974(4) 0.0843(3) 0.0313(7) Uani 1 1 d . . .
C13 C 0.7609(4) 1.0698(4) 0.0236(3) 0.0369(7) Uani 1 1 d . . .
H13 H 0.8515 1.0977 -0.0643 0.044 Uiso 1 1 calc R . .
C14 C 0.6828(4) 1.1990(4) 0.0911(3) 0.0369(7) Uani 1 1 d . . .
H14 H 0.7189 1.3164 0.0484 0.044 Uiso 1 1 calc R . .
C15 C 0.5522(4) 1.1613(4) 0.2204(3) 0.0355(7) Uani 1 1 d . . .
H15 H 0.5005 1.2509 0.2672 0.043 Uiso 1 1 calc R . .
C16 C 0.4985(4) 0.9912(4) 0.2800(3) 0.0326(7) Uani 1 1 d . . .
H16 H 0.4082 0.9648 0.3681 0.039 Uiso 1 1 calc R . .
C17 C 0.5127(4) 0.6763(4) 0.2756(3) 0.0325(7) Uani 1 1 d . . .
O4 O 0.2160(3) 0.3656(2) 0.4871(2) 0.0355(5) Uani 1 1 d . . .
N1 N 0.0469(3) 0.1786(3) 0.4568(2) 0.0285(6) Uani 1 1 d . . .
C21 C -0.0738(4) 0.1344(3) 0.3766(3) 0.0310(7) Uani 1 1 d . . .
H21B H -0.0527 0.2084 0.2703 0.037 Uiso 1 1 calc R . .
H21A H -0.2033 0.1631 0.4199 0.037 Uiso 1 1 calc R . .
C22 C 0.0381(4) 0.0626(3) 0.6130(3) 0.0293(7) Uani 1 1 d . . .
H22B H -0.0846 0.0867 0.6710 0.035 Uiso 1 1 calc R . .
H22A H 0.1302 0.0915 0.6576 0.035 Uiso 1 1 calc R . .
C23 C 0.1262(4) 0.3311(3) 0.4081(3) 0.0281(6) Uani 1 1 d . . .
C24 C 0.1057(4) 0.4588(4) 0.2556(3) 0.0375(8) Uani 1 1 d . . .
H24A H 0.1757 0.5599 0.2332 0.056 Uiso 1 1 calc R . .
H24B H -0.0241 0.5035 0.2537 0.056 Uiso 1 1 calc R . .
H24C H 0.1519 0.3962 0.1806 0.056 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C17 1.325(3) . ?
O1 H1 1.01(5) . ?
O2 C17 1.229(3) . ?
O3 C12 1.356(3) . ?
O3 H3 0.86(5) . ?
C11 C16 1.392(4) . ?
C11 C12 1.401(4) . ?
C11 C17 1.479(4) . ?
C12 C13 1.397(4) . ?
C13 C14 1.375(4) . ?
C13 H13 0.950 . ?
C14 C15 1.386(4) . ?
C14 H14 0.950 . ?
C15 C16 1.379(4) . ?
C15 H15 0.950 . ?
C16 H16 0.950 . ?
O4 C23 1.247(3) . ?
N1 C23 1.345(3) . ?
N1 C21 1.471(3) . ?
N1 C22 1.475(3) . ?
C21 C22 1.516(4) 2_556 ?
C21 H21B 0.990 . ?
C21 H21A 0.990 . ?
C22 C21 1.516(4) 2_556 ?
C22 H22B 0.990 . ?
C22 H22A 0.990 . ?
C23 C24 1.506(4) . ?
C24 H24A 0.980 . ?
C24 H24B 0.980 . ?
C24 H24C 0.980 . ?

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
C17 O1 H1 114(2) . . ?
C12 O3 H3 109(3) . . ?
C16 C11 C12 118.8(2) . . ?
C16 C11 C17 121.6(2) . . ?
C12 C11 C17 119.6(2) . . ?
O3 C12 C13 117.8(3) . . ?
O3 C12 C11 122.4(2) . . ?
C13 C12 C11 119.7(3) . . ?
C14 C13 C12 119.9(3) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 121.3(3) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C16 C15 C14 118.8(3) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C15 C16 C11 121.5(3) . . ?
C15 C16 H16 119.2 . . ?
C11 C16 H16 119.2 . . ?
O2 C17 O1 122.7(2) . . ?
O2 C17 C11 122.4(3) . . ?
O1 C17 C11 114.9(2) . . ?
C23 N1 C21 124.3(2) . . ?
C23 N1 C22 120.8(2) . . ?
C21 N1 C22 113.3(2) . . ?
N1 C21 C22 111.1(2) . 2_556 ?
N1 C21 H21B 109.4 . . ?
C22 C21 H21B 109.4 2_556 . ?
N1 C21 H21A 109.4 . . ?
C22 C21 H21A 109.4 2_556 . ?
H21B C21 H21A 108.0 . . ?
N1 C22 C21 111.6(2) . 2_556 ?
N1 C22 H22B 109.3 . . ?
C21 C22 H22B 109.3 2_556 . ?
N1 C22 H22A 109.3 . . ?
C21 C22 H22A 109.3 2_556 . ?
H22B C22 H22A 108.0 . . ?
O4 C23 N1 120.8(2) . . ?
O4 C23 C24 120.6(2) . . ?
N1 C23 C24 118.6(2) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 C11 C12 O3 178.5(2) . . . . ?
C17 C11 C12 O3 -3.0(4) . . . . ?
C16 C11 C12 C13 -0.3(4) . . . . ?
C17 C11 C12 C13 178.2(2) . . . . ?
O3 C12 C13 C14 -179.0(2) . . . . ?
C11 C12 C13 C14 -0.2(4) . . . . ?
C12 C13 C14 C15 0.9(4) . . . . ?
C13 C14 C15 C16 -1.1(4) . . . . ?
C14 C15 C16 C11 0.6(4) . . . . ?
C12 C11 C16 C15 0.1(4) . . . . ?
C17 C11 C16 C15 -178.4(3) . . . . ?
C16 C11 C17 O2 -176.9(3) . . . . ?
C12 C11 C17 O2 4.7(4) . . . . ?
C16 C11 C17 O1 4.4(4) . . . . ?
C12 C11 C17 O1 -174.0(2) . . . . ?
C23 N1 C21 C22 140.8(3) . . . 2_556 ?
C22 N1 C21 C22 -53.5(3) . . . 2_556 ?
C23 N1 C22 C21 -139.9(3) . . . 2_556 ?
C21 N1 C22 C21 53.8(3) . . . 2_556 ?
C21 N1 C23 O4 174.7(2) . . . . ?
C22 N1 C23 O4 9.9(4) . . . . ?
C21 N1 C23 C24 -5.8(4) . . . . ?
C22 N1 C23 C24 -170.5(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O4 1.01(5) 1.59(5) 2.596(3) 171(4) .
O3 H3 O2 0.86(5) 1.84(5) 2.592(3) 145(4) .

#=============================================================================

data_8
_database_code_depnum_ccdc_archive 'CCDC 692786'

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H14 N2 +, 2(C9 H7 O4 -)'
_chemical_formula_sum            'C24 H28 N2 O8'
_chemical_formula_weight         472.48

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   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   7.4937(4)
_cell_length_b                   10.0957(5)
_cell_length_c                   15.2981(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.025(3)
_cell_angle_gamma                90.00
_cell_volume                     1146.03(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    4209
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      28.13

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             500
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.883
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_process_details   
;
TWINABS (Sheldrick, 2003)
Ratio of minimum to maximum apparent transmission: 0.902004
;

_exptl_special_details           
;
H1 visible in difference Fourier, but placed and allowed to ride.
All N---C bonds of disordered DABCO restrained to single refined value.
;

_diffrn_ambient_temperature      180(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-Nonius X8APEX-II CCD'
_diffrn_measurement_method       'thin-slice ω and φ scans'
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22769
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_sigmaI/netI    0.0293
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.52
_diffrn_reflns_theta_max         28.31
_diffrn_measured_fraction_theta_max 0.966
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.988
_reflns_number_total             2757
_reflns_number_gt                2120
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 v.1.0-22 (Bruker Nonius, 2004)'
_computing_cell_refinement       'SAINT-plus v.7.06a (Bruker, 2003)'
_computing_data_reduction        'SAINT-plus v.7.06a'
_computing_structure_solution    'SHELXTL v.6.10 (Sheldrick, 2000)'
_computing_structure_refinement  'SHELXTL v.6.10'
_computing_molecular_graphics    'SHELXTL v.6.10'
_computing_publication_material  'SHELXTL v.6.10'

_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)+(0.0741P)²+0.4957P] 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         2757
_refine_ls_number_parameters     183
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.1503
_refine_ls_wR_factor_gt          0.1415
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.208
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.051

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.34859(18) 0.58563(14) 0.19597(10) 0.0396(4) Uani 1 1 d . . .
O2 O 0.5445(2) 0.64935(17) 0.10696(10) 0.0467(4) Uani 1 1 d . . .
O3 O 0.51993(17) 0.46739(12) 0.34131(8) 0.0282(3) Uani 1 1 d . . .
O4 O 0.3571(2) 0.60919(19) 0.41002(15) 0.0694(6) Uani 1 1 d . . .
C1 C 0.6461(2) 0.63981(19) 0.26038(13) 0.0310(4) Uani 1 1 d . . .
C2 C 0.6504(2) 0.56496(17) 0.33704(12) 0.0263(4) Uani 1 1 d . . .
C3 C 0.7862(3) 0.5787(2) 0.40751(14) 0.0365(5) Uani 1 1 d . . .
H3A H 0.7880 0.5243 0.4583 0.044 Uiso 1 1 calc R . .
C4 C 0.9193(3) 0.6723(3) 0.40334(17) 0.0533(7) Uani 1 1 d . . .
H4A H 1.0123 0.6834 0.4517 0.064 Uiso 1 1 calc R . .
C5 C 0.9169(3) 0.7499(3) 0.32843(17) 0.0607(8) Uani 1 1 d . . .
H5A H 1.0074 0.8152 0.3258 0.073 Uiso 1 1 calc R . .
C6 C 0.7829(3) 0.7324(2) 0.25736(15) 0.0473(6) Uani 1 1 d . . .
H6A H 0.7842 0.7844 0.2057 0.057 Uiso 1 1 calc R . .
C7 C 0.5050(3) 0.62386(19) 0.18010(13) 0.0331(4) Uani 1 1 d . . .
C8 C 0.3661(3) 0.5082(2) 0.37054(15) 0.0418(5) Uani 1 1 d . . .
C9 C 0.2183(3) 0.4094(3) 0.34831(17) 0.0580(8) Uani 1 1 d . . .
H9A H 0.1160 0.4520 0.3121 0.087 Uiso 1 1 calc R . .
H9B H 0.1800 0.3758 0.4028 0.087 Uiso 1 1 calc R . .
H9C H 0.2619 0.3357 0.3154 0.087 Uiso 1 1 calc R . .
N1 N 0.11606(19) 0.53488(14) 0.06328(11) 0.0318(4) Uani 1 1 d D . .
H1A H 0.2006 0.5606 0.1077 0.038 Uiso 1 1 d R . .
C1A C 0.2056(5) 0.4571(4) 0.0064(2) 0.0329(8) Uani 0.50 1 d PD . .
H1AA H 0.2458 0.3755 0.0348 0.039 Uiso 0.50 1 d PR . .
H1AB H 0.3079 0.5031 -0.0101 0.039 Uiso 0.50 1 d PR . .
C2A C 0.0246(5) 0.6538(3) 0.0294(2) 0.0288(8) Uani 0.50 1 d PD . .
H2AA H 0.1053 0.7107 0.0033 0.035 Uiso 0.50 1 d PR . .
H2AB H -0.0215 0.7013 0.0758 0.035 Uiso 0.50 1 d PR . .
C3A C -0.0196(5) 0.4500(4) 0.1059(2) 0.0311(8) Uani 0.50 1 d PD . .
H3AA H -0.0842 0.5029 0.1432 0.037 Uiso 0.50 1 d PR . .
H3AB H 0.0401 0.3791 0.1401 0.037 Uiso 0.50 1 d PR . .
C4A C -0.1282(5) 0.6084(3) -0.0408(3) 0.0314(8) Uani 0.50 1 d P . .
H4AA H -0.1285 0.6608 -0.0932 0.038 Uiso 0.50 1 d PR . .
H4AB H -0.2406 0.6230 -0.0190 0.038 Uiso 0.50 1 d PR . .
C5A C 0.0670(4) 0.4292(4) -0.0740(3) 0.0356(9) Uani 0.50 1 d P . .
H5AA H 0.0696 0.3367 -0.0882 0.043 Uiso 0.50 1 d PR . .
H5AB H 0.1009 0.4776 -0.1231 0.043 Uiso 0.50 1 d PR . .
C6A C -0.1498(5) 0.3963(4) 0.0256(2) 0.0335(8) Uani 0.50 1 d P . .
H6AA H -0.2725 0.4102 0.0349 0.040 Uiso 0.50 1 d PR . .
H6AB H -0.1314 0.3026 0.0206 0.040 Uiso 0.50 1 d PR . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.289(2) . ?
O2 C7 1.224(2) . ?
O3 C8 1.357(2) . ?
O3 C2 1.396(2) . ?
O4 C8 1.192(3) . ?
C1 C2 1.392(3) . ?
C1 C6 1.393(3) . ?
C1 C7 1.513(3) . ?
C2 C3 1.382(3) . ?
C3 C4 1.382(3) . ?
C3 H3A 0.950 . ?
C4 C5 1.386(3) . ?
C4 H4A 0.950 . ?
C5 C6 1.385(3) . ?
C5 H5A 0.950 . ?
C6 H6A 0.950 . ?
C8 C9 1.494(3) . ?
C9 H9A 0.980 . ?
C9 H9B 0.980 . ?
C9 H9C 0.980 . ?
N1 C1A 1.410(3) . ?
N1 C2A 1.443(3) . ?
N1 C5A 1.450(3) 3_565 ?
N1 C4A 1.492(3) 3_565 ?
N1 C3A 1.542(3) . ?
N1 C6A 1.579(3) 3_565 ?
N1 H1A 0.900 . ?
C1A C5A 1.521(5) . ?
C1A H1AA 0.960 . ?
C1A H1AB 0.960 . ?
C2A C4A 1.526(5) . ?
C2A H2AA 0.960 . ?
C2A H2AB 0.960 . ?
C3A C6A 1.556(5) . ?
C3A H3AA 0.960 . ?
C3A H3AB 0.960 . ?
C4A N1 1.492(3) 3_565 ?
C4A H4AA 0.960 . ?
C4A H4AB 0.960 . ?
C5A N1 1.450(3) 3_565 ?
C5A H5AA 0.960 . ?
C5A H5AB 0.956 . ?
C6A N1 1.579(3) 3_565 ?
C6A H6AA 0.960 . ?
C6A H6AB 0.960 . ?

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
C8 O3 C2 115.71(14) . . ?
C2 C1 C6 117.50(17) . . ?
C2 C1 C7 123.88(16) . . ?
C6 C1 C7 118.59(17) . . ?
C3 C2 C1 122.05(17) . . ?
C3 C2 O3 118.58(16) . . ?
C1 C2 O3 119.25(16) . . ?
C4 C3 C2 119.35(18) . . ?
C4 C3 H3A 120.3 . . ?
C2 C3 H3A 120.3 . . ?
C3 C4 C5 119.9(2) . . ?
C3 C4 H4A 120.0 . . ?
C5 C4 H4A 120.0 . . ?
C6 C5 C4 120.1(2) . . ?
C6 C5 H5A 120.0 . . ?
C4 C5 H5A 120.0 . . ?
C5 C6 C1 121.09(19) . . ?
C5 C6 H6A 119.5 . . ?
C1 C6 H6A 119.5 . . ?
O2 C7 O1 125.28(18) . . ?
O2 C7 C1 119.26(17) . . ?
O1 C7 C1 115.45(17) . . ?
O4 C8 O3 122.50(18) . . ?
O4 C8 C9 126.4(2) . . ?
O3 C8 C9 111.08(18) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C1A N1 H1A 106.4 . . ?
C2A N1 H1A 106.2 . . ?
C3A N1 H1A 106.1 . . ?
C4A N1 H1A 113.3 3_565 . ?
C5A N1 H1A 114.8 3_565 . ?
C6A N1 H1A 110.0 3_565 . ?
C1A N1 C2A 119.0(3) . . ?
C1A N1 C3A 110.5(3) . . ?
C2A N1 C3A 107.8(2) . . ?
C5A N1 C4A 110.9(3) 3_565 3_565 ?
C5A N1 C6A 104.7(2) 3_565 3_565 ?
C4A N1 C6A 101.9(2) 3_565 3_565 ?
N1 C1A C5A 105.8(2) . . ?
N1 C1A H1AA 110.2 . . ?
N1 C1A H1AB 111.1 . . ?
C5A C1A H1AA 110.0 . . ?
C5A C1A H1AB 110.9 . . ?
H1AA C1A H1AB 108.8 . . ?
N1 C2A C4A 106.0(2) . . ?
N1 C2A H2AA 110.6 . . ?
N1 C2A H2AB 110.6 . . ?
C4A C2A H2AA 110.0 . . ?
C4A C2A H2AB 111.0 . . ?
H2AA C2A H2AB 108.7 . . ?
N1 C3A C6A 103.7(2) . . ?
N1 C3A H3AA 111.1 . . ?
N1 C3A H3AB 111.2 . . ?
C6A C3A H3AA 110.5 . . ?
C6A C3A H3AB 111.3 . . ?
H3AA C3A H3AB 109.0 . . ?
N1 C4A C2A 112.9(3) 3_565 . ?
N1 C4A H4AA 109.6 3_565 . ?
N1 C4A H4AB 108.3 3_565 . ?
C2A C4A H4AA 109.6 . . ?
C2A C4A H4AB 108.5 . . ?
H4AA C4A H4AB 107.8 . . ?
N1 C5A C1A 114.4(3) 3_565 . ?
N1 C5A H5AA 108.6 3_565 . ?
N1 C5A H5AB 108.6 3_565 . ?
C1A C5A H5AA 109.3 . . ?
C1A C5A H5AB 108.2 . . ?
H5AA C5A H5AB 107.5 . . ?
C3A C6A N1 111.6(2) . 3_565 ?
N1 C6A H6AA 109.6 3_565 . ?
N1 C6A H6AB 108.8 3_565 . ?
C3A C6A H6AA 109.9 . . ?
C3A C6A H6AB 109.0 . . ?
H6AA C6A H6AB 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.3(3) . . . . ?
C7 C1 C2 C3 177.11(18) . . . . ?
C6 C1 C2 O3 -177.40(18) . . . . ?
C7 C1 C2 O3 1.0(3) . . . . ?
C8 O3 C2 C3 95.2(2) . . . . ?
C8 O3 C2 C1 -88.6(2) . . . . ?
C1 C2 C3 C4 2.1(3) . . . . ?
O3 C2 C3 C4 178.2(2) . . . . ?
C2 C3 C4 C5 -0.9(4) . . . . ?
C3 C4 C5 C6 -0.9(5) . . . . ?
C4 C5 C6 C1 1.7(5) . . . . ?
C2 C1 C6 C5 -0.6(4) . . . . ?
C7 C1 C6 C5 -179.1(2) . . . . ?
C2 C1 C7 O2 -150.7(2) . . . . ?
C6 C1 C7 O2 27.7(3) . . . . ?
C2 C1 C7 O1 30.4(3) . . . . ?
C6 C1 C7 O1 -151.2(2) . . . . ?
C2 O3 C8 O4 -17.7(3) . . . . ?
C2 O3 C8 C9 163.55(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 0.90 1.64 2.536(2) 171.1 .


