Supplementary information (ESI) for CrystEngComm
This journal is (c) The Royal Society of Chemistry 2008

data_global

_journal_coden_Cambridge         1350

loop_
_publ_author_name
'Mihail Barboiu'
'Yves-Marie Legrand'
'Mathieu Michau'
'van der Lee, Arie'

_publ_contact_author_name        'Mihail Barboiu'
_publ_contact_author_address     
;
Institute Europeen Membranes
CNRS
IEM 5635
Pl Eugene Bat,CC 47
Montpellier
F-34095 5
FRANCE
;

_publ_contact_author_email       BARBOIU@IEMM.UNIV-MONTP2.FR

_publ_requested_journal          CrystEngComm

_publ_section_title              
;
Homomeric and heteromeric self-assembly of hybrid
ureido-imidazole compounds
;

data_1
_database_code_depnum_ccdc_archive 'CCDC 651227'
_audit_creation_date             07-05-31
_audit_creation_method           CRYSTALS_ver_12.84

_oxford_structure_analysis_title 'mdbm17 in P 21/n'
_chemical_name_systematic        ?
_chemical_melting_point          ?

_cell_length_a                   11.6630(18)
_cell_length_b                   6.0080(10)
_cell_length_c                   13.328(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.231(8)
_cell_angle_gamma                90
_cell_volume                     933.2(3)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
x+1/2,-y+1/2,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0010 0.0007 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156
;
International Tables Vol C 4.2.6.8 and 6.1.1.4,
dispersion factors from Interpolated values from CXRO/LLNL data
;
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030
;
International Tables Vol C 4.2.6.8 and 6.1.1.4,
dispersion factors from Interpolated values from CXRO/LLNL data
;
N 0.0028 0.0016 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290
;
International Tables Vol C 4.2.6.8 and 6.1.1.4,
dispersion factors from Interpolated values from CXRO/LLNL data
;
O 0.0046 0.0029 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508
;
International Tables Vol C 4.2.6.8 and 6.1.1.4,
dispersion factors from Interpolated values from CXRO/LLNL data
;

_cell_formula_units_Z            4

# Given Formula = C13 H25 N2 O1
# Dc = 1.60 Fooo = 424.00 Mu = 1.01 M = 225.35
# Found Formula = C10 H10 N4 O1
# Dc = 1.44 FOOO = 424.00 Mu = 1.00 M = 202.22

_chemical_formula_sum            'C10 H10 N4 O1'
_chemical_formula_moiety         'C10 H10 N4 O1'
_chemical_compound_source        ?
_chemical_formula_weight         202.22

_cell_measurement_reflns_used    8192
_cell_measurement_theta_min      2
_cell_measurement_theta_max      13
_cell_measurement_temperature    120

_exptl_crystal_description       ?
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.1
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_max          0.30

_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_meas      ?
# Non-dispersive F(000):
_exptl_crystal_F_000             424
_exptl_absorpt_coefficient_mu    0.100

# Sheldrick geometric approximatio 1.00 1.00
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Bruker SMART'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.51091
_diffrn_measurement_method       '\f & \w scans'

# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection       'SMART (Siemens, 1993)'
_computing_cell_refinement       'SAINT (Siemens ,1995)'
_computing_data_reduction        'SAINT (Siemens ,1995)'
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  ?
_diffrn_standards_interval_count ?
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      120
_diffrn_reflns_number            8098
_reflns_number_total             2532
_diffrn_reflns_av_R_equivalents  0.129
# Number of reflections with Friedels Law is 2532
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 2678

_diffrn_reflns_theta_min         2.674
_diffrn_reflns_theta_max         20.945
_diffrn_measured_fraction_theta_max 0.942

_diffrn_reflns_theta_full        20.526
_diffrn_measured_fraction_theta_full 0.954

_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_reflns_limit_h_min              -16
_reflns_limit_h_max              16
_reflns_limit_k_min              0
_reflns_limit_k_max              8
_reflns_limit_l_min              0
_reflns_limit_l_max              18

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -0.37
_refine_diff_density_max         0.47

_refine_ls_number_reflns         2275
_refine_ls_number_restraints     0
_refine_ls_number_parameters     136

#_refine_ls_R_factor_ref 0.0529
_refine_ls_wR_factor_ref         0.0576
_refine_ls_goodness_of_fit_ref   0.9603

#_reflns_number_all 2530
_refine_ls_R_factor_all          0.0568
_refine_ls_wR_factor_all         0.0594

# The I/u(I) cutoff below was used for refinement as
# well as the _gt R-factors:
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                2275
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_gt          0.0576

_refine_ls_shift/su_max          0.000664

# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration .

_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    noref # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
1.54 0.629 0.895
;

_refine_special_details          
;
All atoms were refined anisotropically. Positional coordinated of the hydrogen
atoms were refined independently
;

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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
N1 N 0.02308(7) 0.18323(13) 0.89373(6) 0.0119 1.0000 Uani . . . . . .
C2 C -0.02064(8) -0.01923(15) 0.86042(7) 0.0128 1.0000 Uani . . . . . .
C3 C 0.04738(8) -0.08448(15) 0.78591(7) 0.0131 1.0000 Uani . . . . . .
N4 N 0.13362(7) 0.07165(13) 0.77216(6) 0.0121 1.0000 Uani . . . . . .
C5 C 0.11490(7) 0.22846(14) 0.83931(6) 0.0094 1.0000 Uani . . . . . .
N6 N 0.18267(7) 0.41589(13) 0.84954(6) 0.0112 1.0000 Uani . . . . . .
C7 C 0.19232(8) 0.54141(14) 0.93612(6) 0.0104 1.0000 Uani . . . . . .
O8 O 0.12913(6) 0.51705(12) 1.00620(5) 0.0152 1.0000 Uani . . . . . .
N9 N 0.27976(7) 0.69216(13) 0.93316(6) 0.0125 1.0000 Uani . . . . . .
C10 C 0.30922(8) 0.84775(15) 1.00915(7) 0.0117 1.0000 Uani . . . . . .
C11 C 0.30120(9) 0.79824(16) 1.11067(7) 0.0157 1.0000 Uani . . . . . .
C12 C 0.33539(9) 0.95532(19) 1.18239(8) 0.0193 1.0000 Uani . . . . . .
C13 C 0.37852(10) 1.16011(18) 1.15402(9) 0.0220 1.0000 Uani . . . . . .
C14 C 0.38822(10) 1.20733(17) 1.05277(9) 0.0215 1.0000 Uani . . . . . .
C15 C 0.35355(9) 1.05254(16) 0.98034(8) 0.0164 1.0000 Uani . . . . . .
H16 H 0.2724 0.6568 1.1294 0.0180 1.0000 Uiso . . . . . .
H17 H 0.3278 0.9251 1.2504 0.0211 1.0000 Uiso . . . . . .
H18 H 0.4009 1.2677 1.2018 0.0242 1.0000 Uiso . . . . . .
H19 H 0.4204 1.3433 1.0325 0.0234 1.0000 Uiso . . . . . .
H20 H 0.3629 1.0790 0.9129 0.0185 1.0000 Uiso . . . . . .
H21 H 0.3179 0.6977 0.8766 0.0126 1.0000 Uiso . . . . . .
H22 H 0.2274 0.4528 0.8016 0.0118 1.0000 Uiso . . . . . .
H23 H -0.0075 0.2652 0.9407 0.0138 1.0000 Uiso . . . . . .
H24 H -0.0876 -0.0879 0.8875 0.0131 1.0000 Uiso . . . . . .
H25 H 0.0396 -0.2190 0.7495 0.0130 1.0000 Uiso . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0133(4) 0.0120(4) 0.0109(3) -0.0024(3) 0.0052(3) -0.0010(3)
C2 0.0138(4) 0.0116(4) 0.0132(4) -0.0001(3) 0.0019(3) -0.0018(3)
C3 0.0133(4) 0.0108(4) 0.0153(4) -0.0021(3) 0.0010(3) 0.0011(3)
N4 0.0127(4) 0.0115(4) 0.0124(3) -0.0031(3) 0.0039(3) 0.0015(3)
C5 0.0106(4) 0.0096(4) 0.0081(3) -0.0001(3) 0.0017(3) 0.0015(3)
N6 0.0136(4) 0.0110(3) 0.0095(3) -0.0015(3) 0.0050(3) -0.0023(3)
C7 0.0102(4) 0.0099(4) 0.0111(4) -0.0015(3) 0.0016(3) 0.0013(3)
O8 0.0139(3) 0.0183(3) 0.0138(3) -0.0056(2) 0.0070(2) -0.0022(2)
N9 0.0144(4) 0.0123(3) 0.0110(3) -0.0019(3) 0.0036(3) -0.0032(3)
C10 0.0100(4) 0.0105(4) 0.0146(4) -0.0018(3) 0.0002(3) 0.0010(3)
C11 0.0175(4) 0.0152(4) 0.0144(4) -0.0024(3) 0.0020(3) 0.0002(3)
C12 0.0184(5) 0.0227(5) 0.0167(4) -0.0073(4) -0.0017(3) 0.0036(4)
C13 0.0183(5) 0.0174(5) 0.0295(5) -0.0111(4) -0.0068(4) 0.0031(3)
C14 0.0192(5) 0.0113(4) 0.0337(6) -0.0016(4) -0.0049(4) -0.0013(3)
C15 0.0152(4) 0.0122(4) 0.0216(5) 0.0020(3) -0.0023(3) 0.0003(3)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          2.059(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . C2 . 1.3853(12) yes
N1 . C5 . 1.3443(11) yes
N1 . H23 . 0.883 no
C2 . C3 . 1.3530(13) yes
C2 . H24 . 0.965 no
C3 . N4 . 1.3926(12) yes
C3 . H25 . 0.946 no
N4 . C5 . 1.3234(11) yes
C5 . N6 . 1.3795(11) yes
N6 . C7 . 1.3794(11) yes
N6 . H22 . 0.869 no
C7 . O8 . 1.2210(11) yes
C7 . N9 . 1.3657(12) yes
N9 . C10 . 1.4109(11) yes
N9 . H21 . 0.891 no
C10 . C11 . 1.3921(13) yes
C10 . C15 . 1.3943(13) yes
C11 . C12 . 1.3905(13) yes
C11 . H16 . 0.951 no
C12 . C13 . 1.3873(17) yes
C12 . H17 . 0.933 no
C13 . C14 . 1.3879(17) yes
C13 . H18 . 0.937 no
C14 . C15 . 1.3892(14) yes
C14 . H19 . 0.943 no
C15 . H20 . 0.924 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . N1 . C5 . 107.19(7) yes
C2 . N1 . H23 . 124.3 no
C5 . N1 . H23 . 128.5 no
N1 . C2 . C3 . 105.70(8) yes
N1 . C2 . H24 . 123.3 no
C3 . C2 . H24 . 131.0 no
C2 . C3 . N4 . 110.40(8) yes
C2 . C3 . H25 . 125.2 no
N4 . C3 . H25 . 124.3 no
C3 . N4 . C5 . 104.57(8) yes
N1 . C5 . N4 . 112.13(8) yes
N1 . C5 . N6 . 125.25(8) yes
N4 . C5 . N6 . 122.61(8) yes
C5 . N6 . C7 . 123.82(7) yes
C5 . N6 . H22 . 119.6 no
C7 . N6 . H22 . 116.4 no
N6 . C7 . O8 . 122.85(8) yes
N6 . C7 . N9 . 112.03(8) yes
O8 . C7 . N9 . 125.12(8) yes
C7 . N9 . C10 . 125.45(8) yes
C7 . N9 . H21 . 116.6 no
C10 . N9 . H21 . 117.8 no
N9 . C10 . C11 . 122.17(8) yes
N9 . C10 . C15 . 118.01(8) yes
C11 . C10 . C15 . 119.73(9) yes
C10 . C11 . C12 . 119.65(9) yes
C10 . C11 . H16 . 119.0 no
C12 . C11 . H16 . 121.4 no
C11 . C12 . C13 . 120.79(10) yes
C11 . C12 . H17 . 120.1 no
C13 . C12 . H17 . 119.1 no
C12 . C13 . C14 . 119.37(9) yes
C12 . C13 . H18 . 121.4 no
C14 . C13 . H18 . 119.3 no
C13 . C14 . C15 . 120.41(10) yes
C13 . C14 . H19 . 120.2 no
C15 . C14 . H19 . 119.3 no
C10 . C15 . C14 . 120.03(10) yes
C10 . C15 . H20 . 118.6 no
C14 . C15 . H20 . 121.3 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
N6 . H22 . N4 3_556 161 0.87 2.06 2.893(2) yes
N1 . H23 . O8 2_567 153 0.88 2.07 2.891(2) yes

# Attachment 'yml59_histaPhuree.cif'

data_2
_database_code_depnum_ccdc_archive 'CCDC 651228'
_audit_creation_date             07-05-29
_audit_creation_method           CRYSTALS_ver_12.84

_oxford_structure_analysis_title yml59
_chemical_name_systematic        ?
_chemical_melting_point          ?

_cell_length_a                   9.3860(10)
_cell_length_b                   11.4412(4)
_cell_length_c                   27.4207(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2944.6(3)

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'Pcab '
_symmetry_space_group_name_Hall  '-P 2bc 2ac'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y,z+1/2
x+1/2,-y,-z+1/2
x+1/2,-y+1/2,z
-x+1/2,y+1/2,-z
-x,-y+1/2,z+1/2
x,y+1/2,-z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            8

# Given Formula = C14 H17 N5 O1
# Dc = 1.22 Fooo = 1152.00 Mu = 0.82 M = 271.32
# Found Formula = C14 H17 N5 O1
# Dc = 1.22 FOOO = 1152.00 Mu = 0.82 M = 271.32

_chemical_formula_sum            'C14 H17 N5 O1'
_chemical_formula_moiety         'C12 H14 N4 O, C2 H3 N'
_chemical_compound_source        ?
_chemical_formula_weight         271.32

_cell_measurement_reflns_used    6426
_cell_measurement_theta_min      4.0784
_cell_measurement_theta_max      28.5629
_cell_measurement_temperature    175

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.08
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_max          0.70

_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_meas      ?
# Non-dispersive F(000):
_exptl_crystal_F_000             1152
_exptl_absorpt_coefficient_mu    0.082

# Sheldrick geometric approximatio 1.00 1.00
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
AbsPack - CrysAlis RED (Oxford Diffraction, 2002)
;
_exptl_absorpt_correction_T_min  0.86786
_exptl_absorpt_correction_T_max  1.00000
_diffrn_measurement_device_type  'Oxford Diffraction XCALIBUR'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       \w

_computing_data_collection       'Xcalibur, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis RED, (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis RED, (Oxford Diffraction, 2002)'
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al 1996)'

_diffrn_standards_number         '4 frames'
_diffrn_standards_interval_time  30
_diffrn_standards_decay_%        0.00

_diffrn_ambient_temperature      175
_diffrn_reflns_number            12019
_reflns_number_total             3766
_diffrn_reflns_av_R_equivalents  0.022
# Number of reflections with Friedels Law is 3373
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 3766

_diffrn_reflns_theta_min         4.089
_diffrn_reflns_theta_max         28.593
_diffrn_measured_fraction_theta_max 0.896

_diffrn_reflns_theta_full        26.019
_diffrn_measured_fraction_theta_full 0.993

_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       35
_reflns_limit_h_min              0
_reflns_limit_h_max              12
_reflns_limit_k_min              0
_reflns_limit_k_max              15
_reflns_limit_l_min              0
_reflns_limit_l_max              35

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -0.22
_refine_diff_density_max         0.26

_refine_ls_number_reflns         2127
_refine_ls_number_restraints     0
_refine_ls_number_parameters     181

#_refine_ls_R_factor_ref 0.0453
_refine_ls_wR_factor_ref         0.0442
_refine_ls_goodness_of_fit_ref   1.0831

#_reflns_number_all 3373
_refine_ls_R_factor_all          0.0776
_refine_ls_wR_factor_all         0.0472

# The I/u(I) cutoff below was used for refinement as
# well as the _gt R-factors:
_reflns_threshold_expression     I>2.00u(I)
_reflns_number_gt                2127
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_gt          0.0442

_refine_ls_shift/su_max          0.010181

# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration .

_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
8.74 -10.6 -0.324 0.770 -6.26
;

_refine_special_details          
;
All atoms were refined anisotropically. Positional coordinated of the hydrogen
atoms were refined independently
;

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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
H21 H 0.6200 1.3144 0.0303 0.0500 1.0000 Uiso R . . . . .
H22 H 0.4026 1.2756 0.0752 0.0500 1.0000 Uiso R . . . . .
H23 H 0.4257 1.1322 0.1372 0.0500 1.0000 Uiso R . . . . .
H24 H 0.8115 1.0563 0.1455 0.0500 1.0000 Uiso R . . . . .
H25 H 0.6707 1.0043 0.1642 0.0500 1.0000 Uiso R . . . . .
H26 H 0.6413 0.8909 0.0976 0.0500 1.0000 Uiso R . . . . .
H27 H 0.7988 0.9384 0.0746 0.0500 1.0000 Uiso R . . . . .
H28 H 0.9267 0.8228 0.1193 0.0500 1.0000 Uiso R . . . . .
H29 H 0.9396 0.6812 0.1678 0.0500 1.0000 Uiso R . . . . .
H30 H 0.9786 0.5437 0.2349 0.0391 1.0000 Uiso R . . . . .
H31 H 0.9373 0.3562 0.2653 0.0492 1.0000 Uiso R . . . . .
H32 H 0.7382 0.2501 0.2390 0.0493 1.0000 Uiso R . . . . .
H33 H 0.5813 0.3325 0.1828 0.0439 1.0000 Uiso R . . . . .
H34 H 0.6226 0.5197 0.1515 0.0359 1.0000 Uiso R . . . . .
H35 H 0.8352 0.5040 0.0644 0.0925 1.0000 Uiso R . . . . .
H36 H 0.8849 0.6265 0.0471 0.0925 1.0000 Uiso R . . . . .
H37 H 0.8466 0.5311 0.0091 0.0925 1.0000 Uiso R . . . . .
N1 N 0.70726(14) 1.18312(13) 0.07343(5) 0.0351 1.0000 Uani . . . . . .
C2 C 0.60882(17) 1.25537(16) 0.05682(7) 0.0364 1.0000 Uani . . . . . .
N3 N 0.48506(14) 1.24169(12) 0.07995(5) 0.0325 1.0000 Uani . . . . . .
C4 C 0.50465(17) 1.15518(14) 0.11392(6) 0.0312 1.0000 Uani . . . . . .
C5 C 0.64184(16) 1.11986(13) 0.10979(6) 0.0283 1.0000 Uani . . . . . .
C6 C 0.71980(18) 1.02467(14) 0.13581(6) 0.0347 1.0000 Uani . . . . . .
C7 C 0.74425(19) 0.92101(15) 0.10229(7) 0.0363 1.0000 Uani . . . . . .
N8 N 0.82140(15) 0.82501(12) 0.12504(6) 0.0361 1.0000 Uani . . . . . .
C9 C 0.75443(17) 0.73968(13) 0.14968(6) 0.0275 1.0000 Uani . . . . . .
O10 O 0.62377(11) 0.73505(10) 0.15479(4) 0.0341 1.0000 Uani . . . . . .
N11 N 0.84498(13) 0.65736(11) 0.16861(5) 0.0289 1.0000 Uani . . . . . .
C12 C 0.80692(16) 0.54923(13) 0.18944(6) 0.0262 1.0000 Uani . . . . . .
C13 C 0.68712(17) 0.48650(14) 0.17433(6) 0.0301 1.0000 Uani . . . . . .
C14 C 0.66261(19) 0.37557(15) 0.19310(6) 0.0362 1.0000 Uani . . . . . .
C15 C 0.7552(2) 0.32661(15) 0.22662(7) 0.0415 1.0000 Uani . . . . . .
C16 C 0.8733(2) 0.38952(17) 0.24205(6) 0.0410 1.0000 Uani . . . . . .
C17 C 0.89807(17) 0.50039(15) 0.22370(6) 0.0327 1.0000 Uani . . . . . .
N18 N 0.5661(3) 0.6334(4) 0.04059(9) 0.1080 1.0000 Uani . . . . . .
C19 C 0.6787(3) 0.6018(3) 0.04005(8) 0.0669 1.0000 Uani . . . . . .
C20 C 0.8244(3) 0.5632(3) 0.04000(10) 0.0773 1.0000 Uani . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0226(6) 0.0367(7) 0.0460(8) 0.0063(6) 0.0018(6) -0.0005(6)
C2 0.0267(8) 0.0352(8) 0.0474(9) 0.0080(8) 0.0007(7) -0.0001(7)
N3 0.0211(6) 0.0305(7) 0.0460(8) -0.0004(6) -0.0009(6) 0.0014(5)
C4 0.0264(7) 0.0287(7) 0.0384(8) -0.0003(7) 0.0024(7) -0.0038(7)
C5 0.0248(7) 0.0252(7) 0.0348(8) -0.0034(6) -0.0006(6) -0.0039(6)
C6 0.0330(8) 0.0328(8) 0.0384(8) 0.0041(7) -0.0032(7) 0.0018(7)
C7 0.0333(8) 0.0302(7) 0.0453(10) 0.0054(7) -0.0010(7) 0.0048(7)
N8 0.0232(6) 0.0319(7) 0.0531(8) 0.0071(6) -0.0003(6) 0.0029(6)
C9 0.0206(7) 0.0266(7) 0.0354(7) -0.0064(7) -0.0021(6) 0.0016(6)
O10 0.0169(5) 0.0324(6) 0.0528(7) -0.0029(5) -0.0019(5) 0.0032(5)
N11 0.0164(5) 0.0248(6) 0.0455(8) 0.0005(6) -0.0008(5) -0.0001(5)
C12 0.0228(7) 0.0245(7) 0.0314(7) -0.0054(6) 0.0049(6) 0.0025(6)
C13 0.0239(7) 0.0293(8) 0.0370(8) -0.0039(7) 0.0010(6) -0.0013(6)
C14 0.0347(8) 0.0301(8) 0.0438(9) -0.0073(7) 0.0077(7) -0.0074(7)
C15 0.0529(10) 0.0316(8) 0.0400(9) 0.0043(7) 0.0113(9) -0.0027(9)
C16 0.0458(10) 0.0438(10) 0.0333(9) 0.0054(8) 0.0002(7) 0.0059(9)
C17 0.0310(8) 0.0362(8) 0.0309(8) -0.0039(7) 0.0009(6) 0.0003(7)
N18 0.0687(16) 0.192(3) 0.0638(15) 0.0140(18) 0.0056(12) 0.026(2)
C19 0.0691(16) 0.0929(19) 0.0387(11) 0.0066(11) -0.0046(11) 0.0045(15)
C20 0.0829(19) 0.0890(19) 0.0602(15) 0.0073(13) -0.0160(14) 0.0251(16)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          4.018(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
H21 . C2 . 0.998 no
H22 . N3 . 0.876 no
H23 . C4 . 1.013 no
H24 . C6 . 0.970 no
H25 . C6 . 0.935 no
H26 . C7 . 1.034 no
H27 . C7 . 0.937 no
H28 . N8 . 1.001 no
H29 . N11 . 0.929 no
H30 . C17 . 0.955 no
H31 . C16 . 0.955 no
H32 . C15 . 0.952 no
H33 . C14 . 0.952 no
H34 . C13 . 0.950 no
H35 . C20 . 0.957 no
H36 . C20 . 0.941 no
H37 . C20 . 0.947 no
N1 . C2 . 1.321(2) yes
N1 . C5 . 1.377(2) yes
C2 . N3 . 1.333(2) yes
N3 . C4 . 1.371(2) yes
C4 . C5 . 1.354(2) yes
C5 . C6 . 1.493(2) yes
C6 . C7 . 1.518(2) yes
C7 . N8 . 1.456(2) yes
N8 . C9 . 1.343(2) yes
C9 . O10 . 1.2355(19) yes
C9 . N11 . 1.371(2) yes
N11 . C12 . 1.409(2) yes
C12 . C13 . 1.397(2) yes
C12 . C17 . 1.388(2) yes
C13 . C14 . 1.389(2) yes
C14 . C15 . 1.383(3) yes
C15 . C16 . 1.388(3) yes
C16 . C17 . 1.384(3) yes
N18 . C19 . 1.117(4) yes
C19 . C20 . 1.438(4) yes
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . N1 . C5 . 105.48(13) yes
H21 . C2 . N1 . 127.0 no
H21 . C2 . N3 . 121.2 no
N1 . C2 . N3 . 111.84(15) yes
C2 . N3 . H22 . 130.4 no
C2 . N3 . C4 . 106.92(13) yes
H22 . N3 . C4 . 122.6 no
H23 . C4 . N3 . 121.2 no
H23 . C4 . C5 . 132.1 no
N3 . C4 . C5 . 106.63(14) yes
N1 . C5 . C4 . 109.13(14) yes
N1 . C5 . C6 . 120.72(14) yes
C4 . C5 . C6 . 130.05(15) yes
C5 . C6 . H24 . 107.1 no
C5 . C6 . H25 . 109.8 no
H24 . C6 . H25 . 107.6 no
C5 . C6 . C7 . 110.77(13) yes
H24 . C6 . C7 . 108.8 no
H25 . C6 . C7 . 112.6 no
C6 . C7 . H26 . 101.3 no
C6 . C7 . H27 . 114.1 no
H26 . C7 . H27 . 118.7 no
C6 . C7 . N8 . 113.90(14) yes
H26 . C7 . N8 . 105.5 no
H27 . C7 . N8 . 103.6 no
C7 . N8 . H28 . 116.2 no
C7 . N8 . C9 . 122.07(14) yes
H28 . N8 . C9 . 121.6 no
N8 . C9 . O10 . 123.55(15) yes
N8 . C9 . N11 . 113.55(14) yes
O10 . C9 . N11 . 122.90(15) yes
H29 . N11 . C9 . 112.4 no
H29 . N11 . C12 . 120.7 no
C9 . N11 . C12 . 126.85(13) yes
N11 . C12 . C13 . 122.35(14) yes
N11 . C12 . C17 . 118.14(14) yes
C13 . C12 . C17 . 119.35(15) yes
H34 . C13 . C12 . 120.2 no
H34 . C13 . C14 . 120.3 no
C12 . C13 . C14 . 119.53(16) yes
H33 . C14 . C13 . 119.7 no
H33 . C14 . C15 . 119.4 no
C13 . C14 . C15 . 120.83(16) yes
H32 . C15 . C14 . 120.2 no
H32 . C15 . C16 . 120.2 no
C14 . C15 . C16 . 119.62(16) yes
H31 . C16 . C15 . 119.9 no
H31 . C16 . C17 . 120.2 no
C15 . C16 . C17 . 119.89(17) yes
H30 . C17 . C12 . 119.8 no
H30 . C17 . C16 . 119.4 no
C12 . C17 . C16 . 120.76(16) yes
N18 . C19 . C20 . 178.8(4) yes
C19 . C20 . H35 . 108.5 no
C19 . C20 . H37 . 109.2 no
H35 . C20 . H37 . 109.1 no
C19 . C20 . H36 . 109.7 no
H35 . C20 . H36 . 109.7 no
H37 . C20 . H36 . 110.6 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
N3 . H22 . N1 5_475 166 0.88 1.89 2.751(2) yes
N8 . H28 . O10 5_565 140 1.00 2.19 3.032(2) yes
N11 . H29 . O10 5_565 165 0.93 2.01 2.916(2) yes


# Attachment 'mdbm17_p21c.cif'

data_CRYSTALS_cif
_database_code_depnum_ccdc_archive 'CCDC 676075'
_audit_creation_date             07-05-31
_audit_creation_method           CRYSTALS_ver_12.84

_oxford_structure_analysis_title 'mdbm17 in P 21/n'
_chemical_name_systematic        ?
_chemical_melting_point          ?

_cell_length_a                   11.6630(18)
_cell_length_b                   6.0080(10)
_cell_length_c                   17.365(2)
_cell_angle_alpha                90
_cell_angle_beta                 129.922(8)
_cell_angle_gamma                90
_cell_volume                     933.2(3)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-y+1/2,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0010 0.0007 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156
;
International Tables Vol C 4.2.6.8 and 6.1.1.4,
dispersion factors from Interpolated values from CXRO/LLNL data
;
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030
;
International Tables Vol C 4.2.6.8 and 6.1.1.4,
dispersion factors from Interpolated values from CXRO/LLNL data
;
N 0.0028 0.0016 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290
;
International Tables Vol C 4.2.6.8 and 6.1.1.4,
dispersion factors from Interpolated values from CXRO/LLNL data
;
O 0.0046 0.0029 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508
;
International Tables Vol C 4.2.6.8 and 6.1.1.4,
dispersion factors from Interpolated values from CXRO/LLNL data
;

_cell_formula_units_Z            4

# Given Formula = C13 H25 N2 O1
# Dc = 1.60 Fooo = 424.00 Mu = 1.01 M = 225.35
# Found Formula = C10 H10 N4 O1
# Dc = 1.44 FOOO = 424.00 Mu = 1.00 M = 202.22

_chemical_formula_sum            'C10 H10 N4 O1'
_chemical_formula_moiety         'C10 H10 N4 O1'
_chemical_compound_source        ?
_chemical_formula_weight         202.22

_cell_measurement_reflns_used    8192
_cell_measurement_theta_min      2
_cell_measurement_theta_max      13
_cell_measurement_temperature    120

_exptl_crystal_description       ?
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.1
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_max          0.30

_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_meas      ?
# Non-dispersive F(000):
_exptl_crystal_F_000             424
_exptl_absorpt_coefficient_mu    0.100

# Sheldrick geometric approximatio 1.00 1.00
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Bruker SMART'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.51091
_diffrn_measurement_method       '\f & \w scans'

# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection       'SMART (Siemens, 1993)'
_computing_cell_refinement       'SAINT (Siemens ,1995)'
_computing_data_reduction        'SAINT (Siemens ,1995)'
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  ?
_diffrn_standards_interval_count ?
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      120
_diffrn_reflns_number            8098
_reflns_number_total             2532
_diffrn_reflns_av_R_equivalents  0.079
# Number of reflections with Friedels Law is 2532
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 2678

_diffrn_reflns_theta_min         2.674
_diffrn_reflns_theta_max         20.945
_diffrn_measured_fraction_theta_max 0.942

_diffrn_reflns_theta_full        20.526
_diffrn_measured_fraction_theta_full 0.954

_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       22
_reflns_limit_h_min              -16
_reflns_limit_h_max              12
_reflns_limit_k_min              0
_reflns_limit_k_max              8
_reflns_limit_l_min              0
_reflns_limit_l_max              24

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -0.38
_refine_diff_density_max         0.46

# The current dictionary definitions do not cover the
# situation where the reflections used for refinement were
# selected by a user-defined sigma threshold

# The values actually used during refinement
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_refine_ls_number_reflns         2365
_refine_ls_number_restraints     0
_refine_ls_number_parameters     136
_oxford_refine_ls_R_factor_ref   0.0552
_refine_ls_wR_factor_ref         0.0560
_refine_ls_goodness_of_fit_ref   0.9396
_refine_ls_shift/su_max          0.000233

# The values computed from all data
_oxford_reflns_number_all        2532
_refine_ls_R_factor_all          0.0576
_refine_ls_wR_factor_all         0.0569

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                2365
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_gt          0.0560

# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration .

_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
2.07 1.90 1.79 0.620 0.428
;

_refine_special_details          
;
All atoms were refined anisotropically. Positional coordinated of
the hydrogen
atoms were initially refined with soft restraints on their angles and
distances
in order to optimise their geometries. After that they were treated as
riding on
their parent atoms.
;

_publ_section_references         
;
Burla, M. C., Camalli, M. B., Carrozzini, G. L. , Cascarano, R.,
Giacovazzo, C., Polidori, G., \& Spagna, R. J. Appl. Crystallogr.,
2003, 36, 1103.

Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.

Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R.,
Munksgaard, Copenhagen, 291-294.

Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.

Siemens Industrial Automation, Inc (1993).
SMART: Area-Detector Software Package; Madison, WI.

Siemens Industrial Automation, Inc (1995).
SAINT: Area-Detector Integration Software.; Madison, WI.

Siemens Industrial Automation, Inc (1996).
SADABS: Area-Detector Absorption Correction;: Madison, WI.

Watkin D.J. (1994).
Acta Cryst, A50, 411-437.

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atomsattached to an atom.

# ..._refinement_flags_...
# . no refinement constraints S special position constraint on site
# G rigid group refinement of site R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond) P partial occupancy constraint

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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
N1 N 0.12935(8) 0.81676(12) 0.10627(5) 0.0123 1.0000 Uani . . . . . . .
C2 C 0.11889(10) 1.01916(14) 0.13957(7) 0.0133 1.0000 Uani . . . . . . .
C3 C 0.26150(10) 1.08441(14) 0.21406(7) 0.0135 1.0000 Uani . . . . . . .
N4 N 0.36156(8) 0.92838(12) 0.22787(5) 0.0124 1.0000 Uani . . . . . . .
C5 C 0.27558(9) 0.77155(14) 0.16067(6) 0.0098 1.0000 Uani . . . . . . .
N6 N 0.33311(8) 0.58418(12) 0.15044(5) 0.0116 1.0000 Uani . . . . . . .
C7 C 0.25618(9) 0.45858(14) 0.06386(6) 0.0107 1.0000 Uani . . . . . . .
O8 O 0.12292(7) 0.48309(12) -0.00621(5) 0.0155 1.0000 Uani . . . . . . .
N9 N 0.34666(8) 0.30784(12) 0.06685(5) 0.0128 1.0000 Uani . . . . . . .
C10 C 0.30017(10) 0.15227(14) -0.00906(6) 0.0121 1.0000 Uani . . . . . . .
C11 C 0.19056(11) 0.20175(15) -0.11063(7) 0.0159 1.0000 Uani . . . . . . .
C12 C 0.15299(12) 0.04460(18) -0.18238(7) 0.0196 1.0000 Uani . . . . . . .
C13 C 0.22440(13) -0.16012(17) -0.15406(8) 0.0222 1.0000 Uani . . . . . . .
C14 C 0.33537(13) -0.20734(16) -0.05278(9) 0.0218 1.0000 Uani . . . . . . .
C15 C 0.37320(11) -0.05255(15) 0.01961(7) 0.0167 1.0000 Uani . . . . . . .
H16 H 0.1430 0.3432 -0.1294 0.0500 1.0000 Uiso R . . . . . .
H17 H 0.0774 0.0748 -0.2504 0.0500 1.0000 Uiso R . . . . . .
H18 H 0.1990 -0.2677 -0.2018 0.0500 1.0000 Uiso R . . . . . .
H19 H 0.3878 -0.3433 -0.0325 0.0500 1.0000 Uiso R . . . . . .
H20 H 0.4500 -0.0790 0.0871 0.0500 1.0000 Uiso R . . . . . .
H21 H 0.4414 0.3023 0.1234 0.0500 1.0000 Uiso R . . . . . .
H22 H 0.4258 0.5473 0.1984 0.0500 1.0000 Uiso R . . . . . .
H23 H 0.0518 0.7348 0.0593 0.0500 1.0000 Uiso R . . . . . .
H24 H 0.0249 1.0878 0.1125 0.0500 1.0000 Uiso R . . . . . .
H25 H 0.2901 1.2189 0.2505 0.0500 1.0000 Uiso R . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0076(3) 0.0126(3) 0.0112(3) -0.0026(2) 0.0035(3) -0.0007(2)
C2 0.0125(4) 0.0120(4) 0.0139(4) -0.0002(3) 0.0078(3) 0.0014(3)
C3 0.0140(4) 0.0110(4) 0.0156(4) -0.0023(3) 0.0095(3) -0.0022(3)
N4 0.0093(3) 0.0119(3) 0.0124(3) -0.0031(2) 0.0054(3) -0.0032(2)
C5 0.0085(3) 0.0100(4) 0.0085(3) -0.0002(3) 0.0043(3) -0.0013(3)
N6 0.0075(3) 0.0114(3) 0.0097(3) -0.0016(2) 0.0026(3) 0.0006(2)
C7 0.0095(4) 0.0103(3) 0.0113(3) -0.0016(3) 0.0063(3) -0.0020(3)
O8 0.0074(3) 0.0186(3) 0.0142(3) -0.0056(2) 0.0041(3) -0.0021(2)
N9 0.0098(3) 0.0126(3) 0.0113(3) -0.0021(2) 0.0046(3) 0.0011(2)
C10 0.0125(4) 0.0109(4) 0.0148(4) -0.0019(3) 0.0097(3) -0.0022(3)
C11 0.0152(4) 0.0155(4) 0.0145(4) -0.0023(3) 0.0083(3) -0.0017(3)
C12 0.0200(5) 0.0233(5) 0.0168(4) -0.0073(3) 0.0125(4) -0.0076(3)
C13 0.0312(5) 0.0177(4) 0.0292(5) -0.0110(4) 0.0247(5) -0.0097(4)
C14 0.0314(5) 0.0119(4) 0.0334(5) -0.0016(4) 0.0260(5) -0.0001(3)
C15 0.0212(5) 0.0126(4) 0.0219(4) 0.0021(3) 0.0163(4) 0.0012(3)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          2.079(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . C2 . 1.3850(11) yes
N1 . C5 . 1.3443(11) yes
N1 . H23 . 0.883 no
C2 . C3 . 1.3535(12) yes
C2 . H24 . 0.966 no
C3 . N4 . 1.3924(12) yes
C3 . H25 . 0.945 no
N4 . C5 . 1.3241(10) yes
C5 . N6 . 1.3791(11) yes
N6 . C7 . 1.3798(10) yes
N6 . H22 . 0.869 no
C7 . O8 . 1.2208(11) yes
C7 . N9 . 1.3661(11) yes
N9 . C10 . 1.4099(11) yes
N9 . H21 . 0.891 no
C10 . C11 . 1.3927(12) yes
C10 . C15 . 1.3940(12) yes
C11 . C12 . 1.3910(13) yes
C11 . H16 . 0.951 no
C12 . C13 . 1.3866(16) yes
C12 . H17 . 0.932 no
C13 . C14 . 1.3882(16) yes
C13 . H18 . 0.937 no
C14 . C15 . 1.3885(14) yes
C14 . H19 . 0.943 no
C15 . H20 . 0.923 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . N1 . C5 . 107.21(7) yes
C2 . N1 . H23 . 124.3 no
C5 . N1 . H23 . 128.5 no
N1 . C2 . C3 . 105.66(8) yes
N1 . C2 . H24 . 123.3 no
C3 . C2 . H24 . 131.1 no
C2 . C3 . N4 . 110.47(8) yes
C2 . C3 . H25 . 125.2 no
N4 . C3 . H25 . 124.3 no
C3 . N4 . C5 . 104.49(7) yes
N1 . C5 . N4 . 112.16(8) yes
N1 . C5 . N6 . 125.25(7) yes
N4 . C5 . N6 . 122.58(8) yes
C5 . N6 . C7 . 123.84(7) yes
C5 . N6 . H22 . 119.6 no
C7 . N6 . H22 . 116.3 no
N6 . C7 . O8 . 122.80(8) yes
N6 . C7 . N9 . 112.02(7) yes
O8 . C7 . N9 . 125.18(8) yes
C7 . N9 . C10 . 125.43(7) yes
C7 . N9 . H21 . 116.6 no
C10 . N9 . H21 . 117.8 no
N9 . C10 . C11 . 122.16(8) yes
N9 . C10 . C15 . 118.10(8) yes
C11 . C10 . C15 . 119.64(8) yes
C10 . C11 . C12 . 119.67(9) yes
C10 . C11 . H16 . 118.9 no
C12 . C11 . H16 . 121.4 no
C11 . C12 . C13 . 120.81(10) yes
C11 . C12 . H17 . 120.1 no
C13 . C12 . H17 . 119.1 no
C12 . C13 . C14 . 119.34(9) yes
C12 . C13 . H18 . 121.4 no
C14 . C13 . H18 . 119.2 no
C13 . C14 . C15 . 120.42(9) yes
C13 . C14 . H19 . 120.3 no
C15 . C14 . H19 . 119.3 no
C10 . C15 . C14 . 120.10(9) yes
C10 . C15 . H20 . 118.6 no
C14 . C15 . H20 . 121.3 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
N9 . H21 . N4 3_645 154 0.89 2.22 3.0401(16) yes
N6 . H22 . N4 3_645 161 0.87 2.06 2.8921(16) yes
N1 . H23 . O8 2_565 153 0.88 2.07 2.8913(16) yes

_vrf_DIFF020_CRYSTALS_cif        
;
PROBLEM: _diffrn_standards_interval_count and
RESPONSE: synchrotron measurement; monitor counts are used to
correct for decay
;
_vrf_DIFF022_CRYSTALS_cif        
;
PROBLEM: _diffrn_standards_decay_% is missing
RESPONSE: synchrotron measurement; monitor counts are used to
correct for decay
;

# Attachment 'yml59_pbca.cif'

data_2
_database_code_depnum_ccdc_archive 'CCDC 676076'
_audit_creation_date             07-05-29
_audit_creation_method           CRYSTALS_ver_12.84

_oxford_structure_analysis_title yml59
_chemical_name_systematic        ?
_chemical_melting_point          ?

_cell_length_a                   11.4412(4)
_cell_length_b                   9.3860(10)
_cell_length_c                   27.4207(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2944.6(3)

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

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            8

# Given Formula = C14 H17 N5 O1
# Dc = 1.22 Fooo = 1152.00 Mu = 0.82 M = 271.32
# Found Formula = C14 H17 N5 O1
# Dc = 1.22 FOOO = 1152.00 Mu = 0.82 M = 271.32

_chemical_formula_sum            'C14 H17 N5 O1'
_chemical_formula_moiety         'C12 H14 N4 O, C2 H3 N'
_chemical_compound_source        ?
_chemical_formula_weight         271.32

_cell_measurement_reflns_used    6426
_cell_measurement_theta_min      4.0784
_cell_measurement_theta_max      28.5629
_cell_measurement_temperature    175

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.08
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_max          0.70

_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_meas      ?
# Non-dispersive F(000):
_exptl_crystal_F_000             1152
_exptl_absorpt_coefficient_mu    0.082

# Sheldrick geometric approximatio 1.00 1.00
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
AbsPack - CrysAlis RED (Oxford Diffraction, 2002)
;
_exptl_absorpt_correction_T_min  0.86786
_exptl_absorpt_correction_T_max  1.00000
_diffrn_measurement_device_type  'Oxford Diffraction XCALIBUR'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       \w

_computing_data_collection       'Xcalibur, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis RED, (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis RED, (Oxford Diffraction, 2002)'
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al 1996)'

_diffrn_standards_number         '4 frames'
_diffrn_standards_interval_time  30
_diffrn_standards_decay_%        0.00

_diffrn_ambient_temperature      175
_diffrn_reflns_number            12019
_reflns_number_total             3766
_diffrn_reflns_av_R_equivalents  0.022
# Number of reflections with Friedels Law is 3373
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 3766

_diffrn_reflns_theta_min         4.089
_diffrn_reflns_theta_max         28.593
_diffrn_measured_fraction_theta_max 0.896

_diffrn_reflns_theta_full        26.019
_diffrn_measured_fraction_theta_full 0.993

_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       35
_reflns_limit_h_min              0
_reflns_limit_h_max              15
_reflns_limit_k_min              0
_reflns_limit_k_max              12
_reflns_limit_l_min              0
_reflns_limit_l_max              35

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -0.28
_refine_diff_density_max         0.27

# The current dictionary definitions do not cover the
# situation where the reflections used for refinement were
# selected by a user-defined sigma threshold

# The values actually used during refinement
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_refine_ls_number_reflns         2708
_refine_ls_number_restraints     0
_refine_ls_number_parameters     181
_oxford_refine_ls_R_factor_ref   0.0607
_refine_ls_wR_factor_ref         0.0506
_refine_ls_goodness_of_fit_ref   1.0708
_refine_ls_shift/su_max          0.000287

# The values computed from all data
_oxford_reflns_number_all        3373
_refine_ls_R_factor_all          0.0772
_refine_ls_wR_factor_all         0.0519

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                2708
_refine_ls_R_factor_gt           0.0607
_refine_ls_wR_factor_gt          0.0506

# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration .

_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
12.8 5.92 10.1 4.69
;

_refine_special_details          
;
All atoms were refined anisotropically. Positional coordinated of
the hydrogen
atoms were initially refined with soft restraints on their angles and
distances
in order to optimise their geometries. After that they were treated as
riding on
their parent atoms.
;

_publ_section_references         
;
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.

M. C. Burla, M. B. Camalli, G. L. Carrozzini, R. Cascarano, C.
Giacovazzo, G. Polidori and R. Spagna, J. Appl. Crystallogr.,
2003, 36, 1103.

Oxford Diffraction, (2002) CrysAlis RED.

Oxford Diffraction, (2002) Xcalibur User Manual

Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.

Watkin D.J. (1994),
Acta Cryst, A50, 411-437

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical
Crystallography Laboratory, OXFORD, UK.
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_...
# . no refinement constraints S special position constraint on site
# G rigid group refinement of site R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond) P partial occupancy constraint

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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
N1 N -0.18312(12) 0.70717(13) 0.07342(5) 0.0352 1.0000 Uani . . . . . . .
C2 C -0.25543(14) 0.60869(16) 0.05687(6) 0.0362 1.0000 Uani . . . . . . .
N3 N -0.24171(11) 0.48506(13) 0.07997(5) 0.0324 1.0000 Uani . . . . . . .
C4 C -0.15522(13) 0.50467(16) 0.11389(6) 0.0314 1.0000 Uani . . . . . . .
C5 C -0.11998(12) 0.64186(15) 0.10985(5) 0.0280 1.0000 Uani . . . . . . .
C6 C -0.02460(13) 0.71982(17) 0.13594(6) 0.0347 1.0000 Uani . . . . . . .
C7 C 0.07904(13) 0.74461(18) 0.10228(6) 0.0362 1.0000 Uani . . . . . . .
N8 N 0.17495(11) 0.82147(13) 0.12504(5) 0.0359 1.0000 Uani . . . . . . .
C9 C 0.26035(12) 0.75440(15) 0.14968(5) 0.0273 1.0000 Uani . . . . . . .
O10 O 0.26491(9) 0.62373(10) 0.15477(4) 0.0339 1.0000 Uani . . . . . . .
N11 N 0.34257(10) 0.84491(12) 0.16859(5) 0.0291 1.0000 Uani . . . . . . .
C12 C 0.45066(12) 0.80675(14) 0.18943(5) 0.0259 1.0000 Uani . . . . . . .
C13 C 0.51360(13) 0.68697(15) 0.17431(5) 0.0302 1.0000 Uani . . . . . . .
C14 C 0.62446(13) 0.66280(17) 0.19308(6) 0.0358 1.0000 Uani . . . . . . .
C15 C 0.67348(14) 0.7552(2) 0.22666(6) 0.0415 1.0000 Uani . . . . . . .
C16 C 0.61069(15) 0.87307(19) 0.24199(6) 0.0407 1.0000 Uani . . . . . . .
C17 C 0.49956(14) 0.89807(16) 0.22369(5) 0.0326 1.0000 Uani . . . . . . .
N18 N 0.3665(3) 0.5661(3) 0.04060(8) 0.1075 1.0000 Uani . . . . . . .
C19 C 0.3979(3) 0.6790(3) 0.04007(7) 0.0668 1.0000 Uani . . . . . . .
C20 C 0.4370(3) 0.8239(3) 0.04011(9) 0.0754 1.0000 Uani . . . . . . .
H21 H -0.3108 0.6213 0.0317 0.0500 1.0000 Uiso R . . . . . .
H22 H -0.2756 0.4026 0.0752 0.0500 1.0000 Uiso R . . . . . .
H23 H -0.1297 0.4331 0.1352 0.0500 1.0000 Uiso R . . . . . .
H24 H -0.0550 0.8125 0.1465 0.0500 1.0000 Uiso R . . . . . .
H25 H -0.0016 0.6660 0.1648 0.0500 1.0000 Uiso R . . . . . .
H26 H 0.1081 0.6515 0.0925 0.0500 1.0000 Uiso R . . . . . .
H27 H 0.0552 0.7972 0.0737 0.0500 1.0000 Uiso R . . . . . .
H28 H 0.1772 0.9268 0.1193 0.0500 1.0000 Uiso R . . . . . .
H29 H 0.3187 0.9395 0.1678 0.0500 1.0000 Uiso R . . . . . .
H30 H 0.4556 0.9782 0.2341 0.0500 1.0000 Uiso R . . . . . .
H31 H 0.6422 0.9375 0.2655 0.0500 1.0000 Uiso R . . . . . .
H32 H 0.7500 0.7390 0.2394 0.0500 1.0000 Uiso R . . . . . .
H33 H 0.6678 0.5800 0.1834 0.0500 1.0000 Uiso R . . . . . .
H34 H 0.4807 0.6238 0.1514 0.0500 1.0000 Uiso R . . . . . .
H35 H 0.4892 0.8394 0.0667 0.0500 1.0000 Uiso R . . . . . .
H36 H 0.3710 0.8838 0.0440 0.0500 1.0000 Uiso R . . . . . .
H37 H 0.4742 0.8460 0.0107 0.0500 1.0000 Uiso R . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0366(7) 0.0224(6) 0.0466(8) 0.0020(5) -0.0064(6) 0.0008(5)
C2 0.0354(8) 0.0260(7) 0.0471(8) 0.0010(6) -0.0084(7) -0.0003(6)
N3 0.0304(6) 0.0211(6) 0.0457(7) -0.0007(5) 0.0004(6) -0.0015(5)
C4 0.0292(7) 0.0265(7) 0.0384(7) 0.0025(6) 0.0000(6) 0.0034(6)
C5 0.0247(6) 0.0250(7) 0.0343(7) -0.0002(5) 0.0030(6) 0.0039(5)
C6 0.0325(8) 0.0328(8) 0.0387(8) -0.0037(6) -0.0036(6) -0.0022(6)
C7 0.0302(7) 0.0336(8) 0.0448(9) -0.0030(7) -0.0055(7) -0.0045(7)
N8 0.0314(6) 0.0235(6) 0.0528(8) 0.0003(6) -0.0072(6) -0.0032(5)
C9 0.0261(6) 0.0207(6) 0.0350(7) -0.0023(5) 0.0066(6) -0.0008(5)
O10 0.0324(6) 0.0173(5) 0.0520(6) -0.0018(4) 0.0028(5) -0.0031(4)
N11 0.0247(6) 0.0160(5) 0.0465(7) -0.0005(5) -0.0005(5) 0.0001(5)
C12 0.0249(6) 0.0221(6) 0.0307(7) 0.0047(5) 0.0050(5) -0.0022(5)
C13 0.0295(7) 0.0241(7) 0.0369(7) 0.0016(6) 0.0040(6) 0.0016(6)
C14 0.0295(7) 0.0345(8) 0.0435(8) 0.0077(7) 0.0067(6) 0.0069(6)
C15 0.0318(8) 0.0527(10) 0.0398(8) 0.0114(8) -0.0039(7) 0.0022(8)
C16 0.0431(9) 0.0455(9) 0.0334(8) 0.0004(7) -0.0056(7) -0.0053(8)
C17 0.0359(8) 0.0309(7) 0.0310(7) 0.0010(6) 0.0038(6) -0.0002(6)
N18 0.191(3) 0.0688(15) 0.0626(14) 0.0053(11) -0.0135(16) -0.0259(18)
C19 0.0923(17) 0.0679(15) 0.0401(10) -0.0037(10) -0.0065(10) -0.0049(14)
C20 0.0856(17) 0.0840(17) 0.0567(13) -0.0155(12) -0.0065(12) -0.0233(15)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          4.010(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . C2 . 1.321(2) yes
N1 . C5 . 1.3768(19) yes
C2 . N3 . 1.3312(19) yes
C2 . H21 . 0.944 no
N3 . C4 . 1.371(2) yes
N3 . H22 . 0.876 no
C4 . C5 . 1.354(2) yes
C4 . H23 . 0.937 no
C5 . C6 . 1.496(2) yes
C6 . C7 . 1.521(2) yes
C6 . H24 . 0.980 no
C6 . H25 . 0.976 no
C7 . N8 . 1.4538(19) yes
C7 . H26 . 0.973 no
C7 . H27 . 0.966 no
N8 . C9 . 1.3445(19) yes
N8 . H28 . 1.001 no
C9 . O10 . 1.2354(17) yes
C9 . N11 . 1.3695(18) yes
N11 . C12 . 1.4087(18) yes
N11 . H29 . 0.929 no
C12 . C13 . 1.398(2) yes
C12 . C17 . 1.389(2) yes
C13 . C14 . 1.387(2) yes
C13 . H34 . 0.943 no
C14 . C15 . 1.383(2) yes
C14 . H33 . 0.959 no
C15 . C16 . 1.385(3) yes
C15 . H32 . 0.955 no
C16 . C17 . 1.387(2) yes
C16 . H31 . 0.954 no
C17 . H30 . 0.949 no
N18 . C19 . 1.118(3) yes
C19 . C20 . 1.432(4) yes
C20 . H35 . 0.954 no
C20 . H36 . 0.947 no
C20 . H37 . 0.936 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . N1 . C5 . 105.44(12) yes
N1 . C2 . N3 . 111.88(14) yes
N1 . C2 . H21 . 125.7 no
N3 . C2 . H21 . 122.4 no
C2 . N3 . C4 . 106.91(12) yes
C2 . N3 . H22 . 130.4 no
C4 . N3 . H22 . 122.7 no
N3 . C4 . C5 . 106.69(13) yes
N3 . C4 . H23 . 123.5 no
C5 . C4 . H23 . 129.8 no
N1 . C5 . C4 . 109.06(13) yes
N1 . C5 . C6 . 120.79(13) yes
C4 . C5 . C6 . 130.04(14) yes
C5 . C6 . C7 . 110.70(12) yes
C5 . C6 . H24 . 108.4 no
C7 . C6 . H24 . 108.7 no
C5 . C6 . H25 . 109.3 no
C7 . C6 . H25 . 111.2 no
H24 . C6 . H25 . 108.4 no
C6 . C7 . N8 . 113.83(13) yes
C6 . C7 . H26 . 107.2 no
N8 . C7 . H26 . 107.9 no
C6 . C7 . H27 . 110.5 no
N8 . C7 . H27 . 107.9 no
H26 . C7 . H27 . 109.4 no
C7 . N8 . C9 . 122.13(13) yes
C7 . N8 . H28 . 116.2 no
C9 . N8 . H28 . 121.5 no
N8 . C9 . O10 . 123.53(13) yes
N8 . C9 . N11 . 113.52(12) yes
O10 . C9 . N11 . 122.96(13) yes
C9 . N11 . C12 . 126.79(12) yes
C9 . N11 . H29 . 112.5 no
C12 . N11 . H29 . 120.7 no
N11 . C12 . C13 . 122.44(13) yes
N11 . C12 . C17 . 118.10(13) yes
C13 . C12 . C17 . 119.30(14) yes
C12 . C13 . C14 . 119.49(14) yes
C12 . C13 . H34 . 119.8 no
C14 . C13 . H34 . 120.7 no
C13 . C14 . C15 . 121.00(15) yes
C13 . C14 . H33 . 120.1 no
C15 . C14 . H33 . 118.9 no
C14 . C15 . C16 . 119.51(15) yes
C14 . C15 . H32 . 121.0 no
C16 . C15 . H32 . 119.5 no
C15 . C16 . C17 . 120.06(16) yes
C15 . C16 . H31 . 121.0 no
C17 . C16 . H31 . 118.9 no
C12 . C17 . C16 . 120.63(15) yes
C12 . C17 . H30 . 118.6 no
C16 . C17 . H30 . 120.8 no
N18 . C19 . C20 . 179.1(3) yes
C19 . C20 . H35 . 109.9 no
C19 . C20 . H36 . 108.4 no
H35 . C20 . H36 . 108.8 no
C19 . C20 . H37 . 110.6 no
H35 . C20 . H37 . 110.0 no
H36 . C20 . H37 . 109.2 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
N3 . H22 . N1 3_445 166 0.88 1.89 2.752(2) yes
N8 . H28 . O10 3_555 140 1.00 2.19 3.031(2) yes
N8 . H28 . N18 3_555 129 1.00 2.57 3.295(2) yes
N11 . H29 . O10 3_555 165 0.93 2.01 2.916(2) yes


