# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2017

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

data_dirad10310
_database_code_depnum_ccdc_archive 'CCDC 816632'
_audit_update_record             
;
2011-03-09 deposited with the CCDC.
2017-08-15 downloaded from the CCDC.
;
#TrackingRef '4557_web_deposit_cif_file_2_YuliaBorozdina_1299676307.cif'


_audit_creation_date             10-03-31

_audit_creation_method           CRYSTALS_ver_12.84



_chemical_name_systematic        ?

_chemical_melting_point          ?



_cell_length_a                   10.0305(5)

_cell_length_b                   10.5040(7)

_cell_length_c                   12.3508(6)

_cell_angle_alpha                90

_cell_angle_beta                 102.582(3)

_cell_angle_gamma                90

_cell_volume                     1270.04(12)



_symmetry_cell_setting           Monoclinic

_symmetry_space_group_name_H-M   'P 1 21/c 1 '

_symmetry_space_group_name_Hall  ?

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 0.0033 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'
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'
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'





_cell_formula_units_Z            4



# Given Formula = C13 H15 N3 O2

# Dc = 1.28 Fooo = 520.00 Mu = 0.89 M = 245.28

# Found Formula = C13 H15 N3 O2

# Dc = 1.28 FOOO = 520.00 Mu = 0.89 M = 245.28



_chemical_formula_sum            'C13 H15 N3 O2'

_chemical_formula_moiety         'C13 H15 N3 O2'

_chemical_compound_source        ?

_chemical_formula_weight         245.28





_cell_measurement_reflns_used    0

_cell_measurement_theta_min      0

_cell_measurement_theta_max      0

_cell_measurement_temperature    120



_exptl_crystal_description       prism

_exptl_crystal_colour            'dark blue'

_exptl_crystal_size_min          0.15

_exptl_crystal_size_mid          0.27

_exptl_crystal_size_max          0.41



_exptl_crystal_density_diffrn    1.283

_exptl_crystal_density_meas      ?

# Non-dispersive F(000):

_exptl_crystal_F_000             520

_exptl_absorpt_coefficient_mu    0.089



# Sheldrick geometric approximatio 0.98 0.99

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_process_details   'SORTAV (Blessing)'

_exptl_absorpt_correction_T_min  0.72

_exptl_absorpt_correction_T_max  0.99

# For a Kappa CCD, set Tmin to 1.0 and

# Tmax to the ratio of max:min frame scales in scale_all.log

_diffrn_measurement_device_type  'Nonius KappaCCD'

_diffrn_radiation_monochromator  graphite

_diffrn_radiation_type           'Mo K\a'

_diffrn_radiation_wavelength     0.71073

_diffrn_measurement_method       'φ & ω scans'



# If a reference occurs more than once, delete the author

# and date from subsequent references.

_computing_data_collection       'COLLECT (Nonius, 1997-2001).'

_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'

_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'

_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'

_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            15352

_reflns_number_total             3696

_diffrn_reflns_av_R_equivalents  0.071

# Number of reflections with Friedels Law is 3696

# Number of reflections without Friedels Law is 0

# Theoretical number of reflections is about 3711





_diffrn_reflns_theta_min         2.080

_diffrn_reflns_theta_max         30.019

_diffrn_measured_fraction_theta_max 0.994



_diffrn_reflns_theta_full        28.818

_diffrn_measured_fraction_theta_full 0.995





_diffrn_reflns_limit_h_min       -14

_diffrn_reflns_limit_h_max       14

_diffrn_reflns_limit_k_min       -13

_diffrn_reflns_limit_k_max       14

_diffrn_reflns_limit_l_min       -16

_diffrn_reflns_limit_l_max       17

_reflns_limit_h_min              -14

_reflns_limit_h_max              13

_reflns_limit_k_min              0

_reflns_limit_k_max              14

_reflns_limit_l_min              0

_reflns_limit_l_max              17





_atom_sites_solution_primary     direct #heavy,direct,difmap,geom

# _atom_sites_solution_secondary difmap

_atom_sites_solution_hydrogens   geom



_refine_diff_density_min         -0.26

_refine_diff_density_max         0.40





_refine_ls_number_reflns         2464

_refine_ls_number_restraints     0

_refine_ls_number_parameters     163



#_refine_ls_R_factor_ref 0.0426

_refine_ls_wR_factor_ref         0.0525

_refine_ls_goodness_of_fit_ref   1.0729



#_reflns_number_all 3689

_refine_ls_R_factor_all          0.0668

_refine_ls_wR_factor_all         0.0554



# The I/u(I) cutoff below was used for refinement as

# well as the _gt R-factors:

_reflns_threshold_expression     I>3.0σ(I)

_reflns_number_gt                2464

_refine_ls_R_factor_gt           0.0426

_refine_ls_wR_factor_gt          0.0525



_refine_ls_shift/su_max          0.005867



# 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/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)]

where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax

Method = Robust Weighting (Prince, 1982)

W = [weight] * [1-(deltaF/6*sigmaF)²]²

Ai are:

2.57 0.891 2.04

;



# 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

_atom_site_attached_hydrogens

































O1 O 0.92615(9) 0.10692(10) 0.19121(9) 0.0329 1.0000 Uani . . . . . .
O2 O 0.50158(10) -0.08600(9) 0.12231(9) 0.0326 1.0000 Uani . . . . . .
N1 N 0.77025(12) -0.24244(11) 0.15538(10) 0.0317 1.0000 Uani . . . . . .
N2 N 0.79818(10) 0.08875(10) 0.18377(9) 0.0252 1.0000 Uani . . . . . .
N3 N 0.59708(10) -0.00466(10) 0.15361(9) 0.0253 1.0000 Uani . . . . . .
C1 C 0.97035(13) -0.45371(13) 0.01106(12) 0.0330 1.0000 Uani . . . . . .
C2 C 0.90544(13) -0.34130(13) 0.03949(11) 0.0291 1.0000 Uani . . . . . .
C3 C 0.82842(14) -0.34471(13) 0.12142(12) 0.0325 1.0000 Uani . . . . . .
C4 C 0.79039(12) -0.13105(12) 0.10858(11) 0.0258 1.0000 Uani . . . . . .
C5 C 0.86450(12) -0.11701(12) 0.02652(11) 0.0276 1.0000 Uani . . . . . .
C6 C 0.92140(13) -0.22457(13) -0.01009(12) 0.0295 1.0000 Uani . . . . . .
C7 C 0.72883(12) -0.01826(12) 0.14883(10) 0.0253 1.0000 Uani . . . . . .
C8 C 0.70375(12) 0.19472(12) 0.20053(10) 0.0249 1.0000 Uani . . . . . .
C9 C 0.68298(15) 0.27412(13) 0.09448(11) 0.0318 1.0000 Uani . . . . . .
C10 C 0.76906(13) 0.27372(13) 0.30110(11) 0.0300 1.0000 Uani . . . . . .
C11 C 0.57488(12) 0.11723(12) 0.21167(10) 0.0249 1.0000 Uani . . . . . .
C12 C 0.43967(13) 0.17634(14) 0.15561(13) 0.0345 1.0000 Uani . . . . . .
C13 C 0.57207(15) 0.08004(14) 0.33075(11) 0.0329 1.0000 Uani . . . . . .
H31 H 0.8164 -0.4245 0.1542 0.0428 1.0000 Uiso R . . . . .
H51 H 0.8762 -0.0355 -0.0035 0.0369 1.0000 Uiso R . . . . .
H61 H 0.9696 -0.2196 -0.0682 0.0392 1.0000 Uiso R . . . . .
H91 H 0.6239 0.3436 0.0994 0.0437 1.0000 Uiso R . . . . .
H92 H 0.7687 0.3055 0.0854 0.0437 1.0000 Uiso R . . . . .
H93 H 0.6435 0.2225 0.0327 0.0437 1.0000 Uiso R . . . . .
H101 H 0.7084 0.3401 0.3108 0.0402 1.0000 Uiso R . . . . .
H102 H 0.8520 0.3095 0.2899 0.0402 1.0000 Uiso R . . . . .
H103 H 0.7875 0.2213 0.3653 0.0402 1.0000 Uiso R . . . . .
H121 H 0.4264 0.2529 0.1929 0.0455 1.0000 Uiso R . . . . .
H122 H 0.4402 0.1947 0.0804 0.0455 1.0000 Uiso R . . . . .
H123 H 0.3676 0.1186 0.1586 0.0455 1.0000 Uiso R . . . . .
H131 H 0.5580 0.1537 0.3715 0.0445 1.0000 Uiso R . . . . .
H132 H 0.6567 0.0417 0.3646 0.0445 1.0000 Uiso R . . . . .
H133 H 0.5000 0.0212 0.3302 0.0445 1.0000 Uiso R . . . . .




_refine_ls_extinction_method     None

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



































O1 . N2 . 1.2810(13) yes
O2 . N3 . 1.2790(13) yes
N1 . C3 . 1.3330(17) yes
N1 . C4 . 1.3398(17) yes
N2 . C7 . 1.3427(16) yes
N2 . C8 . 1.5048(16) yes
N3 . C7 . 1.3432(15) yes
N3 . C11 . 1.5076(16) yes
C1 . C1 2_745 1.202(3) yes
C1 . C2 . 1.4287(18) yes
C2 . C3 . 1.401(2) yes
C2 . C6 . 1.3952(19) yes
C3 . H31 . 0.950 no
C4 . C5 . 1.3891(18) yes
C4 . C7 . 1.4717(17) yes
C5 . C6 . 1.3853(18) yes
C5 . H51 . 0.950 no
C6 . H61 . 0.950 no
C8 . C9 . 1.5283(18) yes
C8 . C10 . 1.5186(17) yes
C8 . C11 . 1.5588(17) yes
C9 . H91 . 0.950 no
C9 . H92 . 0.950 no
C9 . H93 . 0.950 no
C10 . H101 . 0.950 no
C10 . H102 . 0.950 no
C10 . H103 . 0.950 no
C11 . C12 . 1.5150(17) yes
C11 . C13 . 1.5279(18) yes
C12 . H121 . 0.950 no
C12 . H122 . 0.950 no
C12 . H123 . 0.950 no
C13 . H131 . 0.950 no
C13 . H132 . 0.950 no
C13 . H133 . 0.950 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






























































C3 . N1 . C4 . 116.78(11) yes
O1 . N2 . C7 . 126.06(11) yes
O1 . N2 . C8 . 122.06(10) yes
C7 . N2 . C8 . 111.46(10) yes
O2 . N3 . C7 . 126.51(11) yes
O2 . N3 . C11 . 122.18(9) yes
C7 . N3 . C11 . 111.10(10) yes
C1 2_745 C1 . C2 . 177.53(19) yes
C1 . C2 . C3 . 120.60(13) yes
C1 . C2 . C6 . 121.09(12) yes
C3 . C2 . C6 . 118.26(12) yes
C2 . C3 . N1 . 123.69(13) yes
C2 . C3 . H31 . 118.1 no
N1 . C3 . H31 . 118.2 no
N1 . C4 . C5 . 124.23(11) yes
N1 . C4 . C7 . 116.33(11) yes
C5 . C4 . C7 . 119.45(11) yes
C4 . C5 . C6 . 118.39(12) yes
C4 . C5 . H51 . 120.8 no
C6 . C5 . H51 . 120.8 no
C2 . C6 . C5 . 118.60(12) yes
C2 . C6 . H61 . 120.4 no
C5 . C6 . H61 . 121.0 no
C4 . C7 . N3 . 126.14(11) yes
C4 . C7 . N2 . 123.80(11) yes
N3 . C7 . N2 . 110.04(10) yes
N2 . C8 . C9 . 104.96(10) yes
N2 . C8 . C10 . 110.14(10) yes
C9 . C8 . C10 . 110.90(11) yes
N2 . C8 . C11 . 100.65(9) yes
C9 . C8 . C11 . 113.57(10) yes
C10 . C8 . C11 . 115.56(10) yes
C8 . C9 . H91 . 109.6 no
C8 . C9 . H92 . 109.4 no
H91 . C9 . H92 . 109.5 no
C8 . C9 . H93 . 109.4 no
H91 . C9 . H93 . 109.5 no
H92 . C9 . H93 . 109.5 no
C8 . C10 . H101 . 109.3 no
C8 . C10 . H102 . 109.4 no
H101 . C10 . H102 . 109.5 no
C8 . C10 . H103 . 109.7 no
H101 . C10 . H103 . 109.5 no
H102 . C10 . H103 . 109.5 no
C8 . C11 . N3 . 100.96(9) yes
C8 . C11 . C12 . 115.00(11) yes
N3 . C11 . C12 . 109.94(10) yes
C8 . C11 . C13 . 114.08(10) yes
N3 . C11 . C13 . 106.05(10) yes
C12 . C11 . C13 . 110.02(11) yes
C11 . C12 . H121 . 109.4 no
C11 . C12 . H122 . 109.6 no
H121 . C12 . H122 . 109.5 no
C11 . C12 . H123 . 109.5 no
H121 . C12 . H123 . 109.5 no
H122 . C12 . H123 . 109.5 no
C11 . C13 . H131 . 109.8 no
C11 . C13 . H132 . 109.2 no
H131 . C13 . H132 . 109.5 no
C11 . C13 . H133 . 109.4 no
H131 . C13 . H133 . 109.5 no
H132 . C13 . H133 . 109.5 no
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_baum0409
_database_code_depnum_ccdc_archive 'CCDC 823717'
_audit_update_record             
;
2011-04-29 deposited with the CCDC.
2017-08-15 downloaded from the CCDC.
;
#TrackingRef '5217_web_deposit_cif_file_1_YuliaBorozdina_1304092185.cif'


_audit_creation_date             11-04-18

_audit_creation_method           CRYSTALS_ver_12.84



_chemical_name_systematic        ?

_chemical_melting_point          ?



_cell_length_a                   6.2359(6)

_cell_length_b                   10.5265(7)

_cell_length_c                   17.6917(9)

_cell_angle_alpha                90

_cell_angle_beta                 94.553(4)

_cell_angle_gamma                90

_cell_volume                     1157.66(15)



_symmetry_cell_setting           Monoclinic

_symmetry_space_group_name_H-M   'P 1 21/n 1 '

_symmetry_space_group_name_Hall  ?

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 0.0033 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'
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'
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'





_cell_formula_units_Z            4



# Given Formula = C13 H16 N2 O1

# Dc = 1.24 Fooo = 464.00 Mu = 0.80 M = 216.28

# Found Formula = C13 H16 N2 O1

# Dc = 1.24 FOOO = 464.00 Mu = 0.80 M = 216.28



_chemical_formula_sum            'C13 H16 N2 O1'

_chemical_formula_moiety         'C13 H16 N2 O1'

_chemical_compound_source        ?

_chemical_formula_weight         216.28





_cell_measurement_reflns_used    0

_cell_measurement_theta_min      0

_cell_measurement_theta_max      0

_cell_measurement_temperature    120



_exptl_crystal_description       prism

_exptl_crystal_colour            red

_exptl_crystal_size_min          0.15

_exptl_crystal_size_mid          0.25

_exptl_crystal_size_max          0.49



_exptl_crystal_density_diffrn    1.241

_exptl_crystal_density_meas      ?

# Non-dispersive F(000):

_exptl_crystal_F_000             464

_exptl_absorpt_coefficient_mu    0.080



# Sheldrick geometric approximatio 0.98 0.99

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_process_details   'SORTAV (Blessing)'

_exptl_absorpt_correction_T_min  0.88

_exptl_absorpt_correction_T_max  0.99

# For a Kappa CCD, set Tmin to 1.0 and

# Tmax to the ratio of max:min frame scales in scale_all.log

_diffrn_measurement_device_type  'Nonius KappaCCD'

_diffrn_radiation_monochromator  graphite

_diffrn_radiation_type           'Mo K\a'

_diffrn_radiation_wavelength     0.71073

_diffrn_measurement_method       'φ & ω scans'



# If a reference occurs more than once, delete the author

# and date from subsequent references.

_computing_data_collection       'COLLECT (Nonius, 1997-2001).'

_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'

_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'

_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'

_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            9103

_reflns_number_total             2527

_diffrn_reflns_av_R_equivalents  0.049

# Number of reflections with Friedels Law is 2527

# Number of reflections without Friedels Law is 0

# Theoretical number of reflections is about 2657





_diffrn_reflns_theta_min         3.902

_diffrn_reflns_theta_max         27.503

_diffrn_measured_fraction_theta_max 0.954



_diffrn_reflns_theta_full        25.028

_diffrn_measured_fraction_theta_full 0.977





_diffrn_reflns_limit_h_min       -8

_diffrn_reflns_limit_h_max       8

_diffrn_reflns_limit_k_min       -12

_diffrn_reflns_limit_k_max       13

_diffrn_reflns_limit_l_min       -22

_diffrn_reflns_limit_l_max       22

_reflns_limit_h_min              -8

_reflns_limit_h_max              8

_reflns_limit_k_min              0

_reflns_limit_k_max              13

_reflns_limit_l_min              0

_reflns_limit_l_max              22





_atom_sites_solution_primary     direct #heavy,direct,difmap,geom

# _atom_sites_solution_secondary difmap

_atom_sites_solution_hydrogens   geom



_refine_diff_density_min         -0.27

_refine_diff_density_max         0.16





_refine_ls_number_reflns         1705

_refine_ls_number_restraints     0

_refine_ls_number_parameters     154



#_refine_ls_R_factor_ref 0.0518

_refine_ls_wR_factor_ref         0.0585

_refine_ls_goodness_of_fit_ref   1.0248



#_reflns_number_all 2524

_refine_ls_R_factor_all          0.0812

_refine_ls_wR_factor_all         0.0641



# The I/u(I) cutoff below was used for refinement as

# well as the _gt R-factors:

_reflns_threshold_expression     I>2.0σ(I)

_reflns_number_gt                1705

_refine_ls_R_factor_gt           0.0518

_refine_ls_wR_factor_gt          0.0585



_refine_ls_shift/su_max          0.000159



# 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/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)]

where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax

Method = Robust Weighting (Prince, 1982)

W = [weight] * [1-(deltaF/6*sigmaF)²]²

Ai are:

2.22 0.868 1.68

;



# 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

_atom_site_attached_hydrogens

































C1 C 0.0566(3) 0.05528(16) 0.01812(8) 0.0273 1.0000 Uani . . . . . .
C2 C -0.0412(3) 0.17368(18) 0.02131(11) 0.0411 1.0000 Uani . . . . . .
C3 C 0.0618(3) 0.27763(17) 0.05567(11) 0.0397 1.0000 Uani . . . . . .
C4 C 0.2699(3) 0.26630(15) 0.08965(9) 0.0279 1.0000 Uani . . . . . .
C5 C 0.3712(3) 0.14875(15) 0.08674(11) 0.0325 1.0000 Uani . . . . . .
C6 C 0.2669(3) 0.04621(16) 0.05134(11) 0.0330 1.0000 Uani . . . . . .
C7 C 0.3780(3) 0.37656(16) 0.12679(9) 0.0283 1.0000 Uani . . . . . .
C8 C 0.4714(3) 0.58489(16) 0.15345(10) 0.0350 1.0000 Uani . . . . . .
C9 C 0.3552(4) 0.69464(19) 0.18812(13) 0.0488 1.0000 Uani . . . . . .
C10 C 0.6057(4) 0.6359(2) 0.09123(13) 0.0571 1.0000 Uani . . . . . .
C11 C 0.5981(3) 0.49634(19) 0.21068(10) 0.0377 1.0000 Uani . . . . . .
C12 C 0.8390(4) 0.5194(3) 0.22120(15) 0.0744 1.0000 Uani . . . . . .
C13 C 0.5061(4) 0.4926(2) 0.28845(10) 0.0448 1.0000 Uani . . . . . .
N1 N 0.3128(2) 0.49682(13) 0.11451(8) 0.0318 1.0000 Uani . . . . . .
N2 N 0.5524(3) 0.36924(16) 0.17614(9) 0.0416 1.0000 Uani . . . . . .
O1 O 0.1794(5) 0.5419(3) 0.06738(15) 0.0441 0.5000 Uani . . . . . .
O2 O 0.6769(5) 0.2851(2) 0.19647(17) 0.0460 0.5000 Uani . . . . . .
H21 H -0.1837 0.1836 -0.0012 0.0522 1.0000 Uiso R . . . . .
H31 H -0.0091 0.3575 0.0561 0.0510 1.0000 Uiso R . . . . .
H51 H 0.5140 0.1391 0.1089 0.0424 1.0000 Uiso R . . . . .
H61 H 0.3396 -0.0330 0.0501 0.0422 1.0000 Uiso R . . . . .
H91 H 0.2722 0.6631 0.2268 0.0628 1.0000 Uiso R . . . . .
H92 H 0.4579 0.7539 0.2094 0.0628 1.0000 Uiso R . . . . .
H93 H 0.2631 0.7354 0.1502 0.0628 1.0000 Uiso R . . . . .
H101 H 0.6782 0.5676 0.0692 0.0741 1.0000 Uiso R . . . . .
H102 H 0.7083 0.6952 0.1125 0.0741 1.0000 Uiso R . . . . .
H103 H 0.5136 0.6767 0.0534 0.0741 1.0000 Uiso R . . . . .
H121 H 0.9022 0.4610 0.2574 0.0880 1.0000 Uiso R . . . . .
H122 H 0.8665 0.6037 0.2384 0.0880 1.0000 Uiso R . . . . .
H123 H 0.8994 0.5072 0.1741 0.0880 1.0000 Uiso R . . . . .
H131 H 0.5906 0.4367 0.3207 0.0582 1.0000 Uiso R . . . . .
H132 H 0.5097 0.5754 0.3099 0.0582 1.0000 Uiso R . . . . .
H133 H 0.3617 0.4630 0.2830 0.0582 1.0000 Uiso R . . . . .




_refine_ls_extinction_method     None

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



































C1 . C1 2_555 1.480(3) yes
C1 . C2 . 1.391(2) yes
C1 . C6 . 1.397(2) yes
C2 . C3 . 1.385(3) yes
C2 . H21 . 0.950 no
C3 . C4 . 1.391(3) yes
C3 . H31 . 0.950 no
C4 . C5 . 1.392(2) yes
C4 . C7 . 1.471(2) yes
C5 . C6 . 1.384(2) yes
C5 . H51 . 0.950 no
C6 . H61 . 0.950 no
C7 . N1 . 1.342(2) yes
C7 . N2 . 1.342(2) yes
C8 . C9 . 1.519(3) yes
C8 . C10 . 1.532(2) yes
C8 . C11 . 1.546(3) yes
C8 . N1 . 1.485(2) yes
C9 . H91 . 0.950 no
C9 . H92 . 0.950 no
C9 . H93 . 0.950 no
C10 . H101 . 0.950 no
C10 . H102 . 0.950 no
C10 . H103 . 0.950 no
C11 . C12 . 1.519(3) yes
C11 . C13 . 1.533(2) yes
C11 . N2 . 1.489(3) yes
C12 . H121 . 0.950 no
C12 . H122 . 0.950 no
C12 . H123 . 0.950 no
C13 . H131 . 0.950 no
C13 . H132 . 0.950 no
C13 . H133 . 0.950 no
N1 . O1 . 1.226(3) yes
N2 . O2 . 1.214(3) 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































































C1 2_555 C1 . C2 . 121.77(19) yes
C1 2_555 C1 . C6 . 121.85(19) yes
C2 . C1 . C6 . 116.38(16) yes
C1 . C2 . C3 . 122.42(17) yes
C1 . C2 . H21 . 118.7 no
C3 . C2 . H21 . 118.8 no
C2 . C3 . C4 . 120.42(16) yes
C2 . C3 . H31 . 120.2 no
C4 . C3 . H31 . 119.4 no
C3 . C4 . C5 . 118.08(15) yes
C3 . C4 . C7 . 120.28(15) yes
C5 . C4 . C7 . 121.64(15) yes
C4 . C5 . C6 . 120.77(15) yes
C4 . C5 . H51 . 119.6 no
C6 . C5 . H51 . 119.7 no
C1 . C6 . C5 . 121.91(15) yes
C1 . C6 . H61 . 118.9 no
C5 . C6 . H61 . 119.2 no
C4 . C7 . N1 . 123.36(15) yes
C4 . C7 . N2 . 124.37(15) yes
N1 . C7 . N2 . 112.27(15) yes
C9 . C8 . C10 . 109.20(16) yes
C9 . C8 . C11 . 115.44(16) yes
C10 . C8 . C11 . 113.68(17) yes
C9 . C8 . N1 . 109.91(16) yes
C10 . C8 . N1 . 105.53(15) yes
C11 . C8 . N1 . 102.38(13) yes
C8 . C9 . H91 . 109.2 no
C8 . C9 . H92 . 109.3 no
H91 . C9 . H92 . 109.5 no
C8 . C9 . H93 . 109.8 no
H91 . C9 . H93 . 109.5 no
H92 . C9 . H93 . 109.5 no
C8 . C10 . H101 . 109.5 no
C8 . C10 . H102 . 109.6 no
H101 . C10 . H102 . 109.5 no
C8 . C10 . H103 . 109.3 no
H101 . C10 . H103 . 109.5 no
H102 . C10 . H103 . 109.5 no
C8 . C11 . C12 . 115.68(19) yes
C8 . C11 . C13 . 113.25(15) yes
C12 . C11 . C13 . 109.35(16) yes
C8 . C11 . N2 . 101.63(14) yes
C12 . C11 . N2 . 110.44(18) yes
C13 . C11 . N2 . 105.79(15) yes
C11 . C12 . H121 . 109.4 no
C11 . C12 . H122 . 109.9 no
H121 . C12 . H122 . 109.5 no
C11 . C12 . H123 . 109.1 no
H121 . C12 . H123 . 109.5 no
H122 . C12 . H123 . 109.5 no
C11 . C13 . H131 . 109.0 no
C11 . C13 . H132 . 109.7 no
H131 . C13 . H132 . 109.5 no
C11 . C13 . H133 . 109.7 no
H131 . C13 . H133 . 109.5 no
H132 . C13 . H133 . 109.5 no
C8 . N1 . C7 . 109.38(14) yes
C8 . N1 . O1 . 117.72(18) yes
C7 . N1 . O1 . 130.98(19) yes
C11 . N2 . C7 . 109.54(15) yes
C11 . N2 . O2 . 115.92(18) yes
C7 . N2 . O2 . 134.5(2) yes



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

data_yubipy
_database_code_depnum_ccdc_archive 'CCDC 858078'
_audit_update_record             
;
2011-12-13 deposited with the CCDC.
2017-08-15 downloaded from the CCDC.
;
#TrackingRef '8639_web_deposit_cif_file_0_YuliaBorozdina_1323780232.biPyIN.cif'


_audit_creation_date             11-12-07

_audit_creation_method           CRYSTALS_ver_12.84



_chemical_name_systematic        ?

_chemical_melting_point          ?



_cell_length_a                   6.3011(2)

_cell_length_b                   10.4759(5)

_cell_length_c                   17.1953(7)

_cell_angle_alpha                90

_cell_angle_beta                 98.045(2)

_cell_angle_gamma                90

_cell_volume                     1123.89(8)



_symmetry_cell_setting           Monoclinic

_symmetry_space_group_name_H-M   'P 1 21/n 1 '

_symmetry_space_group_name_Hall  ?

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 0.0033 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'
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'
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'





_cell_formula_units_Z            4



# Given Formula = C12 H15 N3 O1

# Dc = 1.28 Fooo = 464.00 Mu = 0.85 M = 217.27

# Found Formula = C12 H15 N3 O1

# Dc = 1.28 FOOO = 464.00 Mu = 0.85 M = 217.27



_chemical_formula_sum            'C12 H15 N3 O1'

_chemical_formula_moiety         'C12 H15 N3 O1'

_chemical_compound_source        ?

_chemical_formula_weight         217.27





_cell_measurement_reflns_used    0

_cell_measurement_theta_min      0

_cell_measurement_theta_max      0

_cell_measurement_temperature    120



_exptl_crystal_description       prism

_exptl_crystal_colour            red

_exptl_crystal_size_min          0.13

_exptl_crystal_size_mid          0.19

_exptl_crystal_size_max          0.39



_exptl_crystal_density_diffrn    1.284

_exptl_crystal_density_meas      ?

# Non-dispersive F(000):

_exptl_crystal_F_000             464

_exptl_absorpt_coefficient_mu    0.085



# Sheldrick geometric approximatio 0.98 0.99

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_process_details   'SORTAV (Blessing)'

_exptl_absorpt_correction_T_min  0.92

_exptl_absorpt_correction_T_max  0.99

# For a Kappa CCD, set Tmin to 1.0 and

# Tmax to the ratio of max:min frame scales in scale_all.log

_diffrn_measurement_device_type  'Nonius KappaCCD'

_diffrn_radiation_monochromator  graphite

_diffrn_radiation_type           'Mo K\a'

_diffrn_radiation_wavelength     0.71073

_diffrn_measurement_method       'φ & ω scans'



# If a reference occurs more than once, delete the author

# and date from subsequent references.

_computing_data_collection       'COLLECT (Nonius, 1997-2001).'

_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'

_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'

_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'

_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            13846

_reflns_number_total             3217

_diffrn_reflns_av_R_equivalents  0.077

# Number of reflections with Friedels Law is 3217

# Number of reflections without Friedels Law is 0

# Theoretical number of reflections is about 3275





_diffrn_reflns_theta_min         2.283

_diffrn_reflns_theta_max         30.014

_diffrn_measured_fraction_theta_max 0.979



_diffrn_reflns_theta_full        25.211

_diffrn_measured_fraction_theta_full 0.989





_diffrn_reflns_limit_h_min       -8

_diffrn_reflns_limit_h_max       8

_diffrn_reflns_limit_k_min       -14

_diffrn_reflns_limit_k_max       14

_diffrn_reflns_limit_l_min       -18

_diffrn_reflns_limit_l_max       24

_reflns_limit_h_min              -8

_reflns_limit_h_max              8

_reflns_limit_k_min              0

_reflns_limit_k_max              14

_reflns_limit_l_min              0

_reflns_limit_l_max              24





_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         0.33





_refine_ls_number_reflns         1899

_refine_ls_number_restraints     0

_refine_ls_number_parameters     154



#_refine_ls_R_factor_ref 0.0526

_refine_ls_wR_factor_ref         0.0607

_refine_ls_goodness_of_fit_ref   1.0906



#_reflns_number_all 3209

_refine_ls_R_factor_all          0.0963

_refine_ls_wR_factor_all         0.1944



# The I/u(I) cutoff below was used for refinement as

# well as the _gt R-factors:

_reflns_threshold_expression     I>3.0σ(I)

_reflns_number_gt                1899

_refine_ls_R_factor_gt           0.0526

_refine_ls_wR_factor_gt          0.0607



_refine_ls_shift/su_max          0.004807



# 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/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)]

where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax

Method = Robust Weighting (Prince, 1982)

W = [weight] * [1-(deltaF/6*sigmaF)²]²

Ai are:

1.58 0.600 0.991

;



# 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

_atom_site_attached_hydrogens
































N1 N -0.0508(2) 0.33480(15) 0.02166(9) 0.0282 1.0000 Uani . . . . . .
N2 N 0.5620(3) 0.11889(18) 0.17083(11) 0.0402 1.0000 Uani . . . . . .
N3 N 0.2901(2) 0.00262(14) 0.11192(9) 0.0287 1.0000 Uani . . . . . .
C1 C 0.0598(3) 0.44415(16) 0.01866(9) 0.0218 1.0000 Uani . . . . . .
C2 C 0.2756(3) 0.45461(16) 0.04870(10) 0.0247 1.0000 Uani . . . . . .
C3 C 0.3812(3) 0.34926(17) 0.08331(10) 0.0265 1.0000 Uani . . . . . .
C4 C 0.2694(3) 0.23536(15) 0.08757(9) 0.0221 1.0000 Uani . . . . . .
C5 C 0.0529(3) 0.23291(16) 0.05529(10) 0.0268 1.0000 Uani . . . . . .
C6 C 0.3726(3) 0.11924(17) 0.12332(10) 0.0262 1.0000 Uani . . . . . .
C7 C 0.6012(3) -0.0097(2) 0.20690(11) 0.0340 1.0000 Uani . . . . . .
C8 C 0.5334(4) -0.0008(2) 0.28899(11) 0.0411 1.0000 Uani . . . . . .
C9 C 0.8374(4) -0.0446(3) 0.21274(17) 0.0656 1.0000 Uani . . . . . .
C10 C 0.4486(3) -0.09241(17) 0.14889(11) 0.0315 1.0000 Uani . . . . . .
C11 C 0.3349(4) -0.19960(19) 0.18591(14) 0.0420 1.0000 Uani . . . . . .
C12 C 0.5524(5) -0.1474(2) 0.08070(14) 0.0539 1.0000 Uani . . . . . .
O1 O 0.6954(4) 0.2025(2) 0.18537(15) 0.0432 0.6159 Uani . . . . . .
O2 O 0.1551(7) -0.0329(4) 0.0633(2) 0.0411 0.3841 Uani . . . . . .
H21 H 0.3492 0.5331 0.0452 0.0330 1.0000 Uiso R . . . . .
H31 H 0.5287 0.3542 0.1043 0.0351 1.0000 Uiso R . . . . .
H51 H -0.0244 0.1553 0.0569 0.0369 1.0000 Uiso R . . . . .
H81 H 0.5560 -0.0809 0.3148 0.0518 1.0000 Uiso R . . . . .
H82 H 0.6169 0.0627 0.3185 0.0518 1.0000 Uiso R . . . . .
H83 H 0.3860 0.0213 0.2846 0.0518 1.0000 Uiso R . . . . .
H91 H 0.8607 -0.1266 0.2359 0.0770 1.0000 Uiso R . . . . .
H92 H 0.9215 0.0167 0.2440 0.0770 1.0000 Uiso R . . . . .
H93 H 0.8774 -0.0457 0.1615 0.0770 1.0000 Uiso R . . . . .
H111 H 0.4380 -0.2593 0.2093 0.0523 1.0000 Uiso R . . . . .
H112 H 0.2575 -0.1659 0.2249 0.0523 1.0000 Uiso R . . . . .
H113 H 0.2385 -0.2410 0.1464 0.0523 1.0000 Uiso R . . . . .
H121 H 0.6560 -0.2098 0.0999 0.0654 1.0000 Uiso R . . . . .
H122 H 0.6198 -0.0808 0.0557 0.0654 1.0000 Uiso R . . . . .
H123 H 0.4444 -0.1856 0.0440 0.0654 1.0000 Uiso R . . . . .




_refine_ls_extinction_method     None

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 . C1 . 1.346(2) yes
N1 . C5 . 1.340(2) yes
N2 . C6 . 1.349(2) yes
N2 . C7 . 1.489(3) yes
N2 . O1 . 1.215(3) yes
N3 . C6 . 1.331(2) yes
N3 . C10 . 1.488(2) yes
N3 . O2 . 1.167(4) yes
C1 . C1 2_565 1.488(3) yes
C1 . C2 . 1.390(2) yes
C2 . C3 . 1.380(2) yes
C2 . H21 . 0.950 no
C3 . C4 . 1.393(2) yes
C3 . H31 . 0.950 no
C4 . C5 . 1.399(2) yes
C4 . C6 . 1.473(2) yes
C5 . H51 . 0.950 no
C7 . C8 . 1.534(3) yes
C7 . C9 . 1.523(3) yes
C7 . C10 . 1.550(3) yes
C8 . H81 . 0.950 no
C8 . H82 . 0.950 no
C8 . H83 . 0.950 no
C9 . H91 . 0.950 no
C9 . H92 . 0.950 no
C9 . H93 . 0.950 no
C10 . C11 . 1.519(3) yes
C10 . C12 . 1.532(3) yes
C11 . H111 . 0.950 no
C11 . H112 . 0.950 no
C11 . H113 . 0.950 no
C12 . H121 . 0.950 no
C12 . H122 . 0.950 no
C12 . H123 . 0.950 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





























































C1 . N1 . C5 . 118.08(14) yes
C6 . N2 . C7 . 109.62(15) yes
C6 . N2 . O1 . 130.59(19) yes
C7 . N2 . O1 . 119.78(17) yes
C6 . N3 . C10 . 109.03(15) yes
C6 . N3 . O2 . 128.9(2) yes
C10 . N3 . O2 . 118.1(2) yes
C1 2_565 C1 . N1 . 116.90(18) yes
C1 2_565 C1 . C2 . 120.56(19) yes
N1 . C1 . C2 . 122.54(15) yes
C1 . C2 . C3 . 119.03(16) yes
C1 . C2 . H21 . 120.4 no
C3 . C2 . H21 . 120.6 no
C2 . C3 . C4 . 119.39(15) yes
C2 . C3 . H31 . 120.5 no
C4 . C3 . H31 . 120.1 no
C3 . C4 . C5 . 117.85(15) yes
C3 . C4 . C6 . 122.17(15) yes
C5 . C4 . C6 . 119.97(15) yes
C4 . C5 . N1 . 123.11(16) yes
C4 . C5 . H51 . 118.6 no
N1 . C5 . H51 . 118.2 no
C4 . C6 . N2 . 123.83(17) yes
C4 . C6 . N3 . 123.78(16) yes
N2 . C6 . N3 . 112.39(16) yes
N2 . C7 . C8 . 106.11(17) yes
N2 . C7 . C9 . 110.39(17) yes
C8 . C7 . C9 . 110.46(17) yes
N2 . C7 . C10 . 100.73(14) yes
C8 . C7 . C10 . 113.49(16) yes
C9 . C7 . C10 . 114.9(2) yes
C7 . C8 . H81 . 109.5 no
C7 . C8 . H82 . 109.2 no
H81 . C8 . H82 . 109.5 no
C7 . C8 . H83 . 109.7 no
H81 . C8 . H83 . 109.5 no
H82 . C8 . H83 . 109.5 no
C7 . C9 . H91 . 109.7 no
C7 . C9 . H92 . 109.7 no
H91 . C9 . H92 . 109.5 no
C7 . C9 . H93 . 109.0 no
H91 . C9 . H93 . 109.5 no
H92 . C9 . H93 . 109.5 no
C7 . C10 . N3 . 102.68(14) yes
C7 . C10 . C11 . 115.48(16) yes
N3 . C10 . C11 . 110.22(16) yes
C7 . C10 . C12 . 114.21(18) yes
N3 . C10 . C12 . 104.91(16) yes
C11 . C10 . C12 . 108.65(17) yes
C10 . C11 . H111 . 109.3 no
C10 . C11 . H112 . 109.9 no
H111 . C11 . H112 . 109.5 no
C10 . C11 . H113 . 109.3 no
H111 . C11 . H113 . 109.5 no
H112 . C11 . H113 . 109.5 no
C10 . C12 . H121 . 109.8 no
C10 . C12 . H122 . 109.6 no
H121 . C12 . H122 . 109.5 no
C10 . C12 . H123 . 108.9 no
H121 . C12 . H123 . 109.5 no
H122 . C12 . H123 . 109.5 no



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

data_CRYSTALS_cif
_database_code_depnum_ccdc_archive 'CCDC 810139'
_audit_update_record             
;
2011-01-27 deposited with the CCDC.
2017-08-15 downloaded from the CCDC.
;
#TrackingRef '3995_web_deposit_cif_file_0_YuliaBorozdina_1296119487.cif'

_audit_creation_date             11-01-13
_audit_creation_method           CRYSTALS_ver_12.84

_chemical_name_systematic        
;
2-(4-{4-[4-(1-oxyl-3-oxo-4,4,5,5-tetramethyl-4H,5H-imidazolin-2-yl)
-phenyl]buta-1,3-diyn-1-yl}phenyl)-4,4,5,5-tetramethyl-imidazoline-1-oxyl
;
_chemical_melting_point          228-230C.

_cell_length_a                   6.6883(2)
_cell_length_b                   10.3043(4)
_cell_length_c                   18.2359(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.231(2)
_cell_angle_gamma                90
_cell_volume                     1254.79(7)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  ?
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 0.0033 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            4

# Given Formula = C14 H16 N2 O1
# Dc = 1.21 Fooo = 488.00 Mu = 0.77 M = 228.29
# Found Formula = C14 H16 N2 O1
# Dc = 1.21 FOOO = 488.00 Mu = 0.77 M = 228.29

_chemical_formula_sum            'C14 H16 N2 O1'
_chemical_formula_moiety         'C14 H16 N2 O1'
_chemical_compound_source        ?
_chemical_formula_weight         228.29


_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_temperature    120

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_min          0.13
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_max          0.41

_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_meas      ?
# Non-dispersive F(000):
_exptl_crystal_F_000             488
_exptl_absorpt_coefficient_mu    0.077

# Sheldrick geometric approximatio 0.98 0.99
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SORTAV (Blessing)'
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  0.99
# For a Kappa CCD, set Tmin to 1.0 and
# Tmax to the ratio of max:min frame scales in scale_all.log
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_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            12673
_reflns_number_total             3669
_diffrn_reflns_av_R_equivalents  0.045
# Number of reflections with Friedels Law is 3669
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 3661


_diffrn_reflns_theta_min         2.237
_diffrn_reflns_theta_max         30.001
_diffrn_measured_fraction_theta_max 0.997

_diffrn_reflns_theta_full        30.001
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_reflns_limit_h_min              -9
_reflns_limit_h_max              9
_reflns_limit_k_min              0
_reflns_limit_k_max              14
_reflns_limit_l_min              0
_reflns_limit_l_max              25


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

_refine_diff_density_min         -0.19
_refine_diff_density_max         0.23


_refine_ls_number_reflns         2280
_refine_ls_number_restraints     0
_refine_ls_number_parameters     154

#_refine_ls_R_factor_ref 0.0401
_refine_ls_wR_factor_ref         0.0461
_refine_ls_goodness_of_fit_ref   1.1123

#_reflns_number_all 3663
_refine_ls_R_factor_all          0.0691
_refine_ls_wR_factor_all         0.0553

# The I/u(I) cutoff below was used for refinement as
# well as the _gt R-factors:
_reflns_threshold_expression     I>3.0σ(I)
_reflns_number_gt                2280
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_gt          0.0461

_refine_ls_shift/su_max          0.000347

# 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/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)]
where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)²]²
Ai are:
0.996 0.262 0.604
;

# 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
_atom_site_attached_hydrogens
O1 O 1.23796(15) -0.07285(10) 0.16943(7) 0.0382 1.0000 Uani . . . . . .
N1 N 0.81573(16) 0.11589(10) 0.13254(6) 0.0251 1.0000 Uani . . . . . .
N2 N 1.10553(16) 0.01557(10) 0.16414(6) 0.0239 1.0000 Uani . . . . . .
C5 C 0.82164(19) -0.11458(11) 0.10217(7) 0.0223 1.0000 Uani . . . . . .
C9 C 0.95756(18) 0.21865(12) 0.16046(7) 0.0237 1.0000 Uani . . . . . .
C8 C 0.90993(17) 0.00672(12) 0.13232(6) 0.0213 1.0000 Uani . . . . . .
C6 C 0.9172(2) -0.23494(12) 0.10761(7) 0.0280 1.0000 Uani . . . . . .
C7 C 0.8220(2) -0.34521(12) 0.07906(8) 0.0305 1.0000 Uani . . . . . .
C12 C 1.12938(18) 0.14307(12) 0.20240(7) 0.0237 1.0000 Uani . . . . . .
C2 C 0.6324(2) -0.33762(12) 0.04405(7) 0.0279 1.0000 Uani . . . . . .
C1 C 0.5380(2) -0.45214(13) 0.01299(8) 0.0318 1.0000 Uani . . . . . .
C3 C 0.5364(2) -0.21720(13) 0.03882(8) 0.0313 1.0000 Uani . . . . . .
C4 C 0.6295(2) -0.10755(12) 0.06801(8) 0.0281 1.0000 Uani . . . . . .
C10 C 1.0274(2) 0.28623(13) 0.09170(8) 0.0327 1.0000 Uani . . . . . .
C14 C 1.0906(2) 0.11741(15) 0.28297(8) 0.0359 1.0000 Uani . . . . . .
C11 C 0.8488(2) 0.31572(14) 0.20699(9) 0.0354 1.0000 Uani . . . . . .
C13 C 1.3409(2) 0.19410(14) 0.19533(8) 0.0315 1.0000 Uani . . . . . .
H61 H 1.0478 -0.2411 0.1307 0.0373 1.0000 Uiso R . . . . .
H71 H 0.8872 -0.4270 0.0835 0.0394 1.0000 Uiso R . . . . .
H31 H 0.4070 -0.2106 0.0148 0.0408 1.0000 Uiso R . . . . .
H41 H 0.5621 -0.0264 0.0656 0.0378 1.0000 Uiso R . . . . .
H101 H 1.1185 0.3539 0.1053 0.0434 1.0000 Uiso R . . . . .
H102 H 1.0920 0.2244 0.0625 0.0434 1.0000 Uiso R . . . . .
H103 H 0.9150 0.3214 0.0644 0.0434 1.0000 Uiso R . . . . .
H141 H 1.1049 0.1960 0.3100 0.0461 1.0000 Uiso R . . . . .
H142 H 1.1835 0.0552 0.3028 0.0461 1.0000 Uiso R . . . . .
H143 H 0.9582 0.0852 0.2861 0.0461 1.0000 Uiso R . . . . .
H111 H 0.9393 0.3813 0.2244 0.0469 1.0000 Uiso R . . . . .
H112 H 0.7965 0.2719 0.2475 0.0469 1.0000 Uiso R . . . . .
H113 H 0.7421 0.3542 0.1780 0.0469 1.0000 Uiso R . . . . .
H131 H 1.3552 0.2750 0.2201 0.0416 1.0000 Uiso R . . . . .
H132 H 1.4344 0.1337 0.2167 0.0416 1.0000 Uiso R . . . . .
H133 H 1.3650 0.2055 0.1449 0.0416 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None

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
O1 . N2 . 1.2705(14) yes
N1 . C9 . 1.4920(15) yes
N1 . C8 . 1.2894(16) yes
N2 . C8 . 1.4039(15) yes
N2 . C12 . 1.4919(15) yes
C5 . C8 . 1.4753(16) yes
C5 . C6 . 1.3963(17) yes
C5 . C4 . 1.3981(18) yes
C9 . C12 . 1.5534(18) yes
C9 . C10 . 1.5302(19) yes
C9 . C11 . 1.5228(18) yes
C6 . C7 . 1.3895(18) yes
C6 . H61 . 0.950 no
C7 . C2 . 1.389(2) yes
C7 . H71 . 0.950 no
C12 . C14 . 1.5294(19) yes
C12 . C13 . 1.5214(18) yes
C2 . C1 . 1.4394(17) yes
C2 . C3 . 1.3981(19) yes
C1 . C1 2_645 1.195(3) yes
C3 . C4 . 1.3823(17) yes
C3 . H31 . 0.950 no
C4 . H41 . 0.950 no
C10 . H101 . 0.950 no
C10 . H102 . 0.950 no
C10 . H103 . 0.950 no
C14 . H141 . 0.950 no
C14 . H142 . 0.950 no
C14 . H143 . 0.950 no
C11 . H111 . 0.950 no
C11 . H112 . 0.950 no
C11 . H113 . 0.950 no
C13 . H131 . 0.950 no
C13 . H132 . 0.950 no
C13 . H133 . 0.950 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
C9 . N1 . C8 . 108.59(10) yes
O1 . N2 . C8 . 127.89(10) yes
O1 . N2 . C12 . 122.70(10) yes
C8 . N2 . C12 . 108.85(10) yes
C8 . C5 . C6 . 123.64(11) yes
C8 . C5 . C4 . 117.43(11) yes
C6 . C5 . C4 . 118.91(11) yes
N1 . C9 . C12 . 104.52(9) yes
N1 . C9 . C10 . 105.12(10) yes
C12 . C9 . C10 . 112.35(10) yes
N1 . C9 . C11 . 109.99(10) yes
C12 . C9 . C11 . 114.73(11) yes
C10 . C9 . C11 . 109.57(11) yes
C5 . C8 . N2 . 123.58(11) yes
C5 . C8 . N1 . 123.70(11) yes
N2 . C8 . N1 . 112.71(10) yes
C5 . C6 . C7 . 120.09(13) yes
C5 . C6 . H61 . 119.8 no
C7 . C6 . H61 . 120.1 no
C6 . C7 . C2 . 120.89(12) yes
C6 . C7 . H71 . 119.6 no
C2 . C7 . H71 . 119.5 no
C9 . C12 . N2 . 98.89(9) yes
C9 . C12 . C14 . 113.50(11) yes
N2 . C12 . C14 . 106.12(10) yes
C9 . C12 . C13 . 116.78(11) yes
N2 . C12 . C13 . 109.88(10) yes
C14 . C12 . C13 . 110.50(11) yes
C7 . C2 . C1 . 120.23(13) yes
C7 . C2 . C3 . 119.04(11) yes
C1 . C2 . C3 . 120.73(13) yes
C2 . C1 . C1 2_645 179.1(2) yes
C2 . C3 . C4 . 120.25(13) yes
C2 . C3 . H31 . 119.9 no
C4 . C3 . H31 . 119.9 no
C5 . C4 . C3 . 120.81(12) yes
C5 . C4 . H41 . 119.2 no
C3 . C4 . H41 . 119.9 no
C9 . C10 . H101 . 109.9 no
C9 . C10 . H102 . 108.9 no
H101 . C10 . H102 . 109.5 no
C9 . C10 . H103 . 109.6 no
H101 . C10 . H103 . 109.5 no
H102 . C10 . H103 . 109.5 no
C12 . C14 . H141 . 109.4 no
C12 . C14 . H142 . 109.8 no
H141 . C14 . H142 . 109.5 no
C12 . C14 . H143 . 109.1 no
H141 . C14 . H143 . 109.5 no
H142 . C14 . H143 . 109.5 no
C9 . C11 . H111 . 109.8 no
C9 . C11 . H112 . 109.2 no
H111 . C11 . H112 . 109.5 no
C9 . C11 . H113 . 109.4 no
H111 . C11 . H113 . 109.5 no
H112 . C11 . H113 . 109.5 no
C12 . C13 . H131 . 109.4 no
C12 . C13 . H132 . 109.5 no
H131 . C13 . H132 . 109.5 no
C12 . C13 . H133 . 109.5 no
H131 . C13 . H133 . 109.5 no
H132 . C13 . H133 . 109.5 no


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

data_baum0708
_database_code_depnum_ccdc_archive 'CCDC 823716'
_audit_update_record             
;
2011-04-29 deposited with the CCDC.
2017-08-15 downloaded from the CCDC.
;
#TrackingRef '5216_web_deposit_cif_file_0_YuliaBorozdina_1304092185.cif'


_audit_creation_date             11-04-18

_audit_creation_method           CRYSTALS_ver_12.84



_chemical_name_systematic        ?

_chemical_melting_point          ?



_cell_length_a                   7.3674(2)

_cell_length_b                   13.0178(4)

_cell_length_c                   13.7189(4)

_cell_angle_alpha                90.9445(14)

_cell_angle_beta                 104.4985(16)

_cell_angle_gamma                104.2092(16)

_cell_volume                     1230.61(6)



_symmetry_cell_setting           Triclinic

_symmetry_space_group_name_H-M   'P -1 '

_symmetry_space_group_name_Hall  ?

loop_

_symmetry_equiv_pos_as_xyz


x,y,z
-x,-y,-z



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            4



# Given Formula = C13 H15 N3 O2

# Dc = 1.32 Fooo = 520.00 Mu = 0.92 M = 490.56

# Found Formula = C13 H15 N3 O2

# Dc = 1.32 FOOO = 520.00 Mu = 0.92 M = 490.56



_chemical_formula_sum            'C13 H15 N3 O2'

_chemical_formula_moiety         'C13 H15 N3 O2'

_chemical_compound_source        ?

_chemical_formula_weight         245.28





_cell_measurement_reflns_used    0

_cell_measurement_theta_min      0

_cell_measurement_theta_max      0

_cell_measurement_temperature    120



_exptl_crystal_description       prism

_exptl_crystal_colour            'dark blue'

_exptl_crystal_size_min          0.13

_exptl_crystal_size_mid          0.22

_exptl_crystal_size_max          0.40



_exptl_crystal_density_diffrn    1.324

_exptl_crystal_density_meas      ?

# Non-dispersive F(000):

_exptl_crystal_F_000             520

_exptl_absorpt_coefficient_mu    0.092



# Sheldrick geometric approximatio 0.98 0.99

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_process_details   'SORTAV (Blessing)'

_exptl_absorpt_correction_T_min  0.90

_exptl_absorpt_correction_T_max  0.99

# For a Kappa CCD, set Tmin to 1.0 and

# Tmax to the ratio of max:min frame scales in scale_all.log

_diffrn_measurement_device_type  'Nonius KappaCCD'

_diffrn_radiation_monochromator  graphite

_diffrn_radiation_type           'Mo K\a'

_diffrn_radiation_wavelength     0.71073

_diffrn_measurement_method       'φ & ω scans'



# If a reference occurs more than once, delete the author

# and date from subsequent references.

_computing_data_collection       'COLLECT (Nonius, 1997-2001).'

_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'

_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'

_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'

_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            17610

_reflns_number_total             7176

_diffrn_reflns_av_R_equivalents  0.074

# Number of reflections with Friedels Law is 7176

# Number of reflections without Friedels Law is 0

# Theoretical number of reflections is about 7222





_diffrn_reflns_theta_min         4.361

_diffrn_reflns_theta_max         30.066

_diffrn_measured_fraction_theta_max 0.991



_diffrn_reflns_theta_full        29.464

_diffrn_measured_fraction_theta_full 0.993





_diffrn_reflns_limit_h_min       -10

_diffrn_reflns_limit_h_max       10

_diffrn_reflns_limit_k_min       -18

_diffrn_reflns_limit_k_max       18

_diffrn_reflns_limit_l_min       -19

_diffrn_reflns_limit_l_max       19

_reflns_limit_h_min              -10

_reflns_limit_h_max              9

_reflns_limit_k_min              -18

_reflns_limit_k_max              18

_reflns_limit_l_min              0

_reflns_limit_l_max              19





_atom_sites_solution_primary     direct #heavy,direct,difmap,geom

# _atom_sites_solution_secondary difmap

_atom_sites_solution_hydrogens   geom



_refine_diff_density_min         -0.31

_refine_diff_density_max         0.56





_refine_ls_number_reflns         5587

_refine_ls_number_restraints     0

_refine_ls_number_parameters     325



#_refine_ls_R_factor_ref 0.0524

_refine_ls_wR_factor_ref         0.0618

_refine_ls_goodness_of_fit_ref   0.9857



#_reflns_number_all 7176

_refine_ls_R_factor_all          0.0644

_refine_ls_wR_factor_all         0.0627



# The I/u(I) cutoff below was used for refinement as

# well as the _gt R-factors:

_reflns_threshold_expression     I>3.0σ(I)

_reflns_number_gt                5587

_refine_ls_R_factor_gt           0.0524

_refine_ls_wR_factor_gt          0.0618



_refine_ls_shift/su_max          0.000418



# 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/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)]

where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax

Method = Robust Weighting (Prince, 1982)

W = [weight] * [1-(deltaF/6*sigmaF)²]²

Ai are:

3.30 1.29 2.78

;



# 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

_atom_site_attached_hydrogens


































































O1 O 0.33957(13) 0.79125(8) 0.13151(7) 0.0274 1.0000 Uani . . . . . .
O2 O -0.24721(13) 0.85967(9) -0.02703(7) 0.0323 1.0000 Uani . . . . . .
O3 O 0.63063(13) 0.39860(8) 0.63302(7) 0.0262 1.0000 Uani . . . . . .
O4 O 1.04145(12) 0.25078(7) 0.50352(7) 0.0258 1.0000 Uani . . . . . .
N1 N 0.17791(14) 0.94403(8) 0.34772(7) 0.0222 1.0000 Uani . . . . . .
N2 N 0.19210(13) 0.80172(7) 0.06351(7) 0.0183 1.0000 Uani . . . . . .
N3 N -0.08976(13) 0.83025(8) -0.01125(7) 0.0195 1.0000 Uani . . . . . .
N4 N 1.11202(14) 0.42201(8) 0.86693(7) 0.0201 1.0000 Uani . . . . . .
N5 N 0.69650(13) 0.34775(7) 0.57522(7) 0.0183 1.0000 Uani . . . . . .
N6 N 0.89289(13) 0.27871(7) 0.51343(7) 0.0178 1.0000 Uani . . . . . .
C1 C 0.00071(17) 0.98216(9) 0.45953(9) 0.0217 1.0000 Uani . . . . . .
C2 C 0.00178(16) 0.94141(8) 0.36180(8) 0.0193 1.0000 Uani . . . . . .
C3 C -0.17036(16) 0.90251(9) 0.28649(8) 0.0199 1.0000 Uani . . . . . .
C4 C -0.16326(15) 0.86553(8) 0.19237(8) 0.0184 1.0000 Uani . . . . . .
C5 C 0.01880(15) 0.86851(8) 0.17626(8) 0.0176 1.0000 Uani . . . . . .
C6 C 0.18352(16) 0.90804(9) 0.25732(8) 0.0222 1.0000 Uani . . . . . .
C7 C 0.03906(15) 0.83368(8) 0.07900(8) 0.0172 1.0000 Uani . . . . . .
C8 C -0.03744(15) 0.77766(8) -0.09487(8) 0.0171 1.0000 Uani . . . . . .
C9 C -0.16168(18) 0.66241(9) -0.11255(9) 0.0245 1.0000 Uani . . . . . .
C10 C -0.08468(17) 0.83504(9) -0.18997(8) 0.0223 1.0000 Uani . . . . . .
C11 C 0.18172(15) 0.78927(8) -0.04702(8) 0.0176 1.0000 Uani . . . . . .
C12 C 0.31313(16) 0.89210(9) -0.0686(1) 0.0243 1.0000 Uani . . . . . .
C13 C 0.25567(19) 0.69425(10) -0.06750(10) 0.0263 1.0000 Uani . . . . . .
C14 C 1.44033(16) 0.48013(8) 0.96166(9) 0.0198 1.0000 Uani . . . . . .
C15 C 1.30133(15) 0.43655(8) 0.86848(8) 0.0182 1.0000 Uani . . . . . .
C16 C 1.36176(16) 0.41320(9) 0.78385(8) 0.0211 1.0000 Uani . . . . . .
C17 C 1.22324(15) 0.37674(9) 0.69320(8) 0.0207 1.0000 Uani . . . . . .
C18 C 1.02732(15) 0.36479(8) 0.68942(8) 0.0168 1.0000 Uani . . . . . .
C19 C 0.98057(15) 0.38672(9) 0.77957(8) 0.0195 1.0000 Uani . . . . . .
C20 C 0.87645(15) 0.33074(8) 0.59579(8) 0.0169 1.0000 Uani . . . . . .
C21 C 0.72277(16) 0.27102(9) 0.42443(8) 0.0209 1.0000 Uani . . . . . .
C22 C 0.7903(2) 0.36152(13) 0.36151(11) 0.0346 1.0000 Uani . . . . . .
C23 C 0.67225(19) 0.16337(12) 0.36547(10) 0.0317 1.0000 Uani . . . . . .
C24 C 0.56806(15) 0.28961(9) 0.47711(8) 0.0192 1.0000 Uani . . . . . .
C25 C 0.44544(17) 0.18719(10) 0.50498(10) 0.0261 1.0000 Uani . . . . . .
C26 C 0.43994(18) 0.35838(10) 0.42246(9) 0.0253 1.0000 Uani . . . . . .
H31 H -0.2915 0.9013 0.2996 0.0263 1.0000 Uiso R . . . . .
H41 H -0.2788 0.8389 0.1399 0.0247 1.0000 Uiso R . . . . .
H61 H 0.3068 0.9100 0.2467 0.0285 1.0000 Uiso R . . . . .
H91 H -0.1328 0.6263 -0.1652 0.0323 1.0000 Uiso R . . . . .
H92 H -0.2952 0.6617 -0.1311 0.0323 1.0000 Uiso R . . . . .
H93 H -0.1338 0.6278 -0.0522 0.0323 1.0000 Uiso R . . . . .
H101 H -0.0522 0.8021 -0.2432 0.0303 1.0000 Uiso R . . . . .
H102 H -0.0122 0.9073 -0.1774 0.0303 1.0000 Uiso R . . . . .
H103 H -0.2194 0.8315 -0.2086 0.0303 1.0000 Uiso R . . . . .
H121 H 0.3126 0.8887 -0.1379 0.0325 1.0000 Uiso R . . . . .
H122 H 0.2662 0.9507 -0.0536 0.0325 1.0000 Uiso R . . . . .
H123 H 0.4417 0.9009 -0.0279 0.0325 1.0000 Uiso R . . . . .
H131 H 0.2495 0.6861 -0.1373 0.0346 1.0000 Uiso R . . . . .
H132 H 0.3862 0.7050 -0.0288 0.0346 1.0000 Uiso R . . . . .
H133 H 0.1774 0.6320 -0.0492 0.0346 1.0000 Uiso R . . . . .
H161 H 1.4956 0.4220 0.7884 0.0277 1.0000 Uiso R . . . . .
H171 H 1.2605 0.3602 0.6346 0.0273 1.0000 Uiso R . . . . .
H191 H 0.8475 0.3757 0.7779 0.0262 1.0000 Uiso R . . . . .
H221 H 0.6883 0.3610 0.3031 0.0461 1.0000 Uiso R . . . . .
H222 H 0.8240 0.4276 0.4006 0.0461 1.0000 Uiso R . . . . .
H223 H 0.9001 0.3521 0.3417 0.0461 1.0000 Uiso R . . . . .
H231 H 0.5643 0.1587 0.3090 0.0412 1.0000 Uiso R . . . . .
H232 H 0.7802 0.1558 0.3426 0.0412 1.0000 Uiso R . . . . .
H233 H 0.6404 0.1085 0.4078 0.0412 1.0000 Uiso R . . . . .
H251 H 0.3608 0.1470 0.4453 0.0350 1.0000 Uiso R . . . . .
H252 H 0.3712 0.2045 0.5473 0.0350 1.0000 Uiso R . . . . .
H253 H 0.5283 0.1465 0.5398 0.0350 1.0000 Uiso R . . . . .
H261 H 0.3587 0.3216 0.3604 0.0335 1.0000 Uiso R . . . . .
H262 H 0.3621 0.3734 0.4638 0.0335 1.0000 Uiso R . . . . .
H263 H 0.5197 0.4231 0.4093 0.0335 1.0000 Uiso R . . . . .




_refine_ls_extinction_method     None

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






































































O1 . N2 . 1.2801(12) yes
O2 . N3 . 1.2784(12) yes
O3 . N5 . 1.2788(12) yes
O4 . N6 . 1.2715(12) yes
N1 . C2 . 1.3514(14) yes
N1 . C6 . 1.3324(14) yes
N2 . C7 . 1.3554(13) yes
N2 . C11 . 1.5031(13) yes
N3 . C7 . 1.3508(13) yes
N3 . C8 . 1.5028(13) yes
N4 . C15 . 1.3553(13) yes
N4 . C19 . 1.3295(14) yes
N5 . C20 . 1.3584(13) yes
N5 . C24 . 1.5024(13) yes
N6 . C20 . 1.3542(13) yes
N6 . C21 . 1.4966(14) yes
C1 . C1 2_576 1.200(2) yes
C1 . C2 . 1.4362(15) yes
C2 . C3 . 1.3942(15) yes
C3 . C4 . 1.3882(14) yes
C3 . H31 . 0.950 no
C4 . C5 . 1.4045(14) yes
C4 . H41 . 0.950 no
C5 . C6 . 1.4046(14) yes
C5 . C7 . 1.4564(13) yes
C6 . H61 . 0.950 no
C8 . C9 . 1.5330(15) yes
C8 . C10 . 1.5210(15) yes
C8 . C11 . 1.5515(15) yes
C9 . H91 . 0.950 no
C9 . H92 . 0.950 no
C9 . H93 . 0.950 no
C10 . H101 . 0.950 no
C10 . H102 . 0.950 no
C10 . H103 . 0.950 no
C11 . C12 . 1.5290(15) yes
C11 . C13 . 1.5171(15) yes
C12 . H121 . 0.950 no
C12 . H122 . 0.950 no
C12 . H123 . 0.950 no
C13 . H131 . 0.950 no
C13 . H132 . 0.950 no
C13 . H133 . 0.950 no
C14 . C14 2_867 1.201(2) yes
C14 . C15 . 1.4284(14) yes
C15 . C16 . 1.3972(15) yes
C16 . C17 . 1.3859(15) yes
C16 . H161 . 0.950 no
C17 . C18 . 1.4008(14) yes
C17 . H171 . 0.950 no
C18 . C19 . 1.4070(14) yes
C18 . C20 . 1.4513(13) yes
C19 . H191 . 0.950 no
C21 . C22 . 1.5301(18) yes
C21 . C23 . 1.5206(17) yes
C21 . C24 . 1.5564(15) yes
C22 . H221 . 0.950 no
C22 . H222 . 0.950 no
C22 . H223 . 0.950 no
C23 . H231 . 0.950 no
C23 . H232 . 0.950 no
C23 . H233 . 0.950 no
C24 . C25 . 1.5291(16) yes
C24 . C26 . 1.5289(16) yes
C25 . H251 . 0.950 no
C25 . H252 . 0.950 no
C25 . H253 . 0.950 no
C26 . H261 . 0.950 no
C26 . H262 . 0.950 no
C26 . H263 . 0.950 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 . C6 . 117.46(10) yes
O1 . N2 . C7 . 126.52(9) yes
O1 . N2 . C11 . 121.51(8) yes
C7 . N2 . C11 . 111.71(8) yes
O2 . N3 . C7 . 126.41(9) yes
O2 . N3 . C8 . 121.35(9) yes
C7 . N3 . C8 . 112.05(8) yes
C15 . N4 . C19 . 117.55(9) yes
O3 . N5 . C20 . 126.66(9) yes
O3 . N5 . C24 . 121.25(9) yes
C20 . N5 . C24 . 111.85(8) yes
O4 . N6 . C20 . 126.76(9) yes
O4 . N6 . C21 . 120.65(9) yes
C20 . N6 . C21 . 111.94(9) yes
C1 2_576 C1 . C2 . 178.83(16) yes
C1 . C2 . N1 . 116.14(10) yes
C1 . C2 . C3 . 121.15(10) yes
N1 . C2 . C3 . 122.70(10) yes
C2 . C3 . C4 . 119.49(10) yes
C2 . C3 . H31 . 120.2 no
C4 . C3 . H31 . 120.3 no
C3 . C4 . C5 . 118.50(10) yes
C3 . C4 . H41 . 120.8 no
C5 . C4 . H41 . 120.7 no
C4 . C5 . C6 . 117.66(9) yes
C4 . C5 . C7 . 121.90(9) yes
C6 . C5 . C7 . 120.43(9) yes
C5 . C6 . N1 . 124.18(10) yes
C5 . C6 . H61 . 117.9 no
N1 . C6 . H61 . 118.0 no
C5 . C7 . N2 . 125.82(9) yes
C5 . C7 . N3 . 125.61(9) yes
N2 . C7 . N3 . 108.55(9) yes
N3 . C8 . C9 . 106.91(9) yes
N3 . C8 . C10 . 109.08(9) yes
C9 . C8 . C10 . 109.95(9) yes
N3 . C8 . C11 . 100.71(8) yes
C9 . C8 . C11 . 114.07(9) yes
C10 . C8 . C11 . 115.31(9) yes
C8 . C9 . H91 . 109.5 no
C8 . C9 . H92 . 109.6 no
H91 . C9 . H92 . 109.5 no
C8 . C9 . H93 . 109.3 no
H91 . C9 . H93 . 109.5 no
H92 . C9 . H93 . 109.5 no
C8 . C10 . H101 . 109.5 no
C8 . C10 . H102 . 109.5 no
H101 . C10 . H102 . 109.5 no
C8 . C10 . H103 . 109.4 no
H101 . C10 . H103 . 109.5 no
H102 . C10 . H103 . 109.5 no
C8 . C11 . N2 . 101.01(8) yes
C8 . C11 . C12 . 113.64(9) yes
N2 . C11 . C12 . 105.57(8) yes
C8 . C11 . C13 . 115.58(9) yes
N2 . C11 . C13 . 109.28(9) yes
C12 . C11 . C13 . 110.74(9) yes
C11 . C12 . H121 . 109.4 no
C11 . C12 . H122 . 109.3 no
H121 . C12 . H122 . 109.5 no
C11 . C12 . H123 . 109.7 no
H121 . C12 . H123 . 109.5 no
H122 . C12 . H123 . 109.5 no
C11 . C13 . H131 . 109.6 no
C11 . C13 . H132 . 109.5 no
H131 . C13 . H132 . 109.5 no
C11 . C13 . H133 . 109.3 no
H131 . C13 . H133 . 109.5 no
H132 . C13 . H133 . 109.5 no
C14 2_867 C14 . C15 . 177.68(15) yes
C14 . C15 . N4 . 116.54(10) yes
C14 . C15 . C16 . 120.53(10) yes
N4 . C15 . C16 . 122.91(10) yes
C15 . C16 . C17 . 118.91(10) yes
C15 . C16 . H161 . 120.6 no
C17 . C16 . H161 . 120.5 no
C16 . C17 . C18 . 118.89(10) yes
C16 . C17 . H171 . 120.6 no
C18 . C17 . H171 . 120.5 no
C17 . C18 . C19 . 117.91(9) yes
C17 . C18 . C20 . 121.36(9) yes
C19 . C18 . C20 . 120.73(9) yes
C18 . C19 . N4 . 123.75(10) yes
C18 . C19 . H191 . 118.1 no
N4 . C19 . H191 . 118.1 no
C18 . C20 . N5 . 125.75(9) yes
C18 . C20 . N6 . 125.72(9) yes
N5 . C20 . N6 . 108.52(9) yes
N6 . C21 . C22 . 104.95(9) yes
N6 . C21 . C23 . 109.43(10) yes
C22 . C21 . C23 . 111.24(11) yes
N6 . C21 . C24 . 101.21(8) yes
C22 . C21 . C24 . 113.57(10) yes
C23 . C21 . C24 . 115.34(10) yes
C21 . C22 . H221 . 109.4 no
C21 . C22 . H222 . 109.5 no
H221 . C22 . H222 . 109.5 no
C21 . C22 . H223 . 109.5 no
H221 . C22 . H223 . 109.5 no
H222 . C22 . H223 . 109.5 no
C21 . C23 . H231 . 109.3 no
C21 . C23 . H232 . 109.6 no
H231 . C23 . H232 . 109.5 no
C21 . C23 . H233 . 109.6 no
H231 . C23 . H233 . 109.5 no
H232 . C23 . H233 . 109.5 no
C21 . C24 . N5 . 100.63(8) yes
C21 . C24 . C25 . 113.55(9) yes
N5 . C24 . C25 . 106.00(9) yes
C21 . C24 . C26 . 115.02(9) yes
N5 . C24 . C26 . 109.64(9) yes
C25 . C24 . C26 . 111.04(9) yes
C24 . C25 . H251 . 109.6 no
C24 . C25 . H252 . 109.3 no
H251 . C25 . H252 . 109.5 no
C24 . C25 . H253 . 109.5 no
H251 . C25 . H253 . 109.5 no
H252 . C25 . H253 . 109.5 no
C24 . C26 . H261 . 109.6 no
C24 . C26 . H262 . 109.4 no
H261 . C26 . H262 . 109.5 no
C24 . C26 . H263 . 109.4 no
H261 . C26 . H263 . 109.5 no
H262 . C26 . H263 . 109.5 no
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_yul0710
_database_code_depnum_ccdc_archive 'CCDC 816630'
_audit_update_record             
;
2011-03-09 deposited with the CCDC.
2017-08-15 downloaded from the CCDC.
;
#TrackingRef '4555_web_deposit_cif_file_0_YuliaBorozdina_1299676307.cif'

_audit_creation_date             10-08-02
_audit_creation_method           CRYSTALS_ver_12.84

_chemical_name_systematic        ?
_chemical_melting_point          ?

_cell_length_a                   7.0420(3)
_cell_length_b                   12.9582(9)
_cell_length_c                   14.2234(9)
_cell_angle_alpha                94.407(3)
_cell_angle_beta                 103.761(3)
_cell_angle_gamma                102.863(3)
_cell_volume                     1217.41(13)

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

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'
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'
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'


_cell_formula_units_Z            4

# Given Formula = C13 H20 N3 O1
# Dc = 1.28 Fooo = 488.00 Mu = 0.83 M = 468.64
# Found Formula = C13 H15 N3 O1
# Dc = 1.25 FOOO = 488.00 Mu = 0.82 M = 458.56

_chemical_formula_sum            'C13 H15 N3 O1'
_chemical_formula_moiety         'C13 H15 N3 O1'
_chemical_compound_source        ?
_chemical_formula_weight         229.28


_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_temperature    120

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_min          0.14
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_max          0.33

_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_meas      ?
# Non-dispersive F(000):
_exptl_crystal_F_000             488
_exptl_absorpt_coefficient_mu    0.082

# Sheldrick geometric approximatio 0.98 0.99
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SORTAV (Blessing)'
_exptl_absorpt_correction_T_min  0.73
_exptl_absorpt_correction_T_max  0.99
# For a Kappa CCD, set Tmin to 1.0 and
# Tmax to the ratio of max:min frame scales in scale_all.log
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_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            13273
_reflns_number_total             6769
_diffrn_reflns_av_R_equivalents  0.075
# Number of reflections with Friedels Law is 6769
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 6833


_diffrn_reflns_theta_min         4.461
_diffrn_reflns_theta_max         29.577
_diffrn_measured_fraction_theta_max 0.922

_diffrn_reflns_theta_full        25.141
_diffrn_measured_fraction_theta_full 0.951


_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       19
_reflns_limit_h_min              -9
_reflns_limit_h_max              9
_reflns_limit_k_min              -17
_reflns_limit_k_max              17
_reflns_limit_l_min              0
_reflns_limit_l_max              19


_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         0.40


_refine_ls_number_reflns         5287
_refine_ls_number_restraints     0
_refine_ls_number_parameters     334

#_refine_ls_R_factor_ref 0.0621
_refine_ls_wR_factor_ref         0.0550
_refine_ls_goodness_of_fit_ref   0.9779

#_reflns_number_all 6312
_refine_ls_R_factor_all          0.0619
_refine_ls_wR_factor_all         0.0549

# The I/u(I) cutoff below was used for refinement as
# well as the _gt R-factors:
_reflns_threshold_expression     I>3.0σ(I)
_reflns_number_gt                5287
_refine_ls_R_factor_gt           0.0621
_refine_ls_wR_factor_gt          0.0550

_refine_ls_shift/su_max          0.001567

# 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/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)]
where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)²]²
Ai are:
2.13 2.01 1.04
;

# 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
_atom_site_attached_hydrogens
O1 O 0.12872(12) 0.40476(7) 0.12754(5) 0.0428 1.0000 Uani . . . . . .
N1 N 0.60339(12) 0.41867(6) 0.36338(5) 0.0317 1.0000 Uani . . . . . .
N2 N 0.19883(11) 0.35109(6) 0.07180(5) 0.0282 1.0000 Uani . . . . . .
N3 N 0.42935(12) 0.28428(7) 0.01963(5) 0.0324 1.0000 Uani . . . . . .
N21 N 0.68389(15) 0.09952(8) 0.20829(7) 0.0418 1.0000 Uani . . . . . .
C1 C 0.94158(14) 0.48022(7) 0.46249(7) 0.0318 1.0000 Uani . . . . . .
C2 C 0.80253(13) 0.43622(7) 0.36824(6) 0.0273 1.0000 Uani . . . . . .
C3 C 0.87609(13) 0.41760(8) 0.28761(7) 0.0320 1.0000 Uani . . . . . .
C4 C 0.73979(13) 0.38221(7) 0.19745(6) 0.0296 1.0000 Uani . . . . . .
C5 C 0.53379(12) 0.36705(6) 0.19001(6) 0.0246 1.0000 Uani . . . . . .
C6 C 0.47531(14) 0.38458(7) 0.27574(6) 0.0294 1.0000 Uani . . . . . .
C7 C 0.39036(13) 0.33254(7) 0.09297(6) 0.0257 1.0000 Uani . . . . . .
C8 C 0.25610(15) 0.27472(8) -0.06703(7) 0.0343 1.0000 Uani . . . . . .
C9 C 0.2148(2) 0.16704(10) -0.12967(8) 0.0505 1.0000 Uani . . . . . .
C10 C 0.3277(2) 0.36527(11) -0.12368(8) 0.0484 1.0000 Uani . . . . . .
C11 C 0.07934(14) 0.29039(7) -0.02471(7) 0.0309 1.0000 Uani . . . . . .
C12 C -0.04815(19) 0.18730(10) -0.00469(9) 0.0488 1.0000 Uani . . . . . .
C13 C -0.05666(18) 0.35537(10) -0.07925(8) 0.0445 1.0000 Uani . . . . . .
C21 C 0.49831(15) 0.01831(7) 0.03941(7) 0.0319 1.0000 Uani . . . . . .
C22 C 0.49975(15) 0.06150(7) 0.13659(6) 0.0302 1.0000 Uani . . . . . .
C23 C 0.32114(12) 0.06064(7) 0.15284(6) 0.0266 1.0000 Uani . . . . . .
C24 C 0.31822(14) 0.09730(8) 0.24218(7) 0.0347 1.0000 Uani . . . . . .
C25 C 0.49143(13) 0.13582(7) 0.31975(6) 0.0274 1.0000 Uani . . . . . .
C26 C 0.67727(13) 0.13749(7) 0.30171(6) 0.0294 1.0000 Uani . . . . . .
C27 C 0.48287(14) 0.17009(7) 0.41960(6) 0.0283 1.0000 Uani . . . . . .
C28 C 0.56884(15) 0.21883(8) 0.58281(6) 0.0333 1.0000 Uani . . . . . .
C29 C 0.69164(19) 0.33326(9) 0.61741(9) 0.0477 1.0000 Uani . . . . . .
C30 C 0.6263(2) 0.15049(12) 0.66306(11) 0.0591 1.0000 Uani . . . . . .
C31 C 0.33706(15) 0.20841(8) 0.54649(7) 0.0338 1.0000 Uani . . . . . .
C32 C 0.2620(3) 0.30256(14) 0.57691(13) 0.0682 1.0000 Uani . . . . . .
C33 C 0.2044(2) 0.10834(16) 0.56798(14) 0.0754 1.0000 Uani . . . . . .
O211 O 0.16539(15) 0.21426(9) 0.37865(7) 0.0433 0.7657 Uani . . . . . .
N221 N 0.3192(2) 0.20184(11) 0.44118(9) 0.0293 0.7657 Uani . . . . . .
N231 N 0.6285(3) 0.17348(13) 0.49819(13) 0.0307 0.7657 Uani . . . . . .
O212 O 0.1244(6) 0.1026(4) 0.3889(3) 0.0612 0.2343 Uani . . . . . .
N222 N 0.2985(6) 0.1503(4) 0.4398(3) 0.0356 0.2343 Uani . . . . . .
N232 N 0.6317(10) 0.2102(4) 0.4852(4) 0.0300 0.2343 Uani . . . . . .
H31 H 1.0169 0.4299 0.2937 0.0417 1.0000 Uiso R . . . . .
H41 H 0.7830 0.3674 0.1406 0.0391 1.0000 Uiso R . . . . .
H61 H 0.3351 0.3714 0.2714 0.0443 1.0000 Uiso R . . . . .
H91 H 0.1040 0.1609 -0.1848 0.0587 1.0000 Uiso R . . . . .
H92 H 0.3306 0.1616 -0.1510 0.0587 1.0000 Uiso R . . . . .
H93 H 0.1831 0.1114 -0.0919 0.0587 1.0000 Uiso R . . . . .
H101 H 0.2228 0.3641 -0.1802 0.0594 1.0000 Uiso R . . . . .
H102 H 0.3620 0.4325 -0.0840 0.0594 1.0000 Uiso R . . . . .
H103 H 0.4429 0.3542 -0.1428 0.0594 1.0000 Uiso R . . . . .
H121 H -0.1287 0.1454 -0.0645 0.0599 1.0000 Uiso R . . . . .
H122 H -0.1331 0.2047 0.0336 0.0599 1.0000 Uiso R . . . . .
H123 H 0.0377 0.1480 0.0300 0.0599 1.0000 Uiso R . . . . .
H131 H -0.1339 0.3162 -0.1408 0.0483 1.0000 Uiso R . . . . .
H132 H 0.0252 0.4205 -0.0889 0.0483 1.0000 Uiso R . . . . .
H133 H -0.1448 0.3704 -0.0418 0.0483 1.0000 Uiso R . . . . .
H231 H 0.1996 0.0336 0.1027 0.0314 1.0000 Uiso R . . . . .
H241 H 0.1910 0.0971 0.2541 0.0445 1.0000 Uiso R . . . . .
H261 H 0.7976 0.1621 0.3530 0.0349 1.0000 Uiso R . . . . .
H291 H 0.6567 0.3775 0.5692 0.0579 1.0000 Uiso R . . . . .
H292 H 0.6669 0.3591 0.6766 0.0579 1.0000 Uiso R . . . . .
H293 H 0.8306 0.3343 0.6284 0.0579 1.0000 Uiso R . . . . .
H301 H 0.5495 0.0786 0.6434 0.0696 1.0000 Uiso R . . . . .
H302 H 0.6021 0.1778 0.7218 0.0696 1.0000 Uiso R . . . . .
H303 H 0.7658 0.1531 0.6737 0.0696 1.0000 Uiso R . . . . .
H321 H 0.1199 0.2881 0.5508 0.0793 1.0000 Uiso R . . . . .
H322 H 0.2934 0.3136 0.6462 0.0793 1.0000 Uiso R . . . . .
H323 H 0.3257 0.3649 0.5544 0.0793 1.0000 Uiso R . . . . .
H331 H 0.0662 0.1075 0.5435 0.0843 1.0000 Uiso R . . . . .
H332 H 0.2333 0.1060 0.6364 0.0843 1.0000 Uiso R . . . . .
H333 H 0.2318 0.0480 0.5365 0.0843 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
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
O1 . N2 . 1.2690(10) yes
N1 . C2 . 1.3537(12) yes
N1 . C6 . 1.3288(11) yes
N2 . C7 . 1.3892(11) yes
N2 . C11 . 1.4836(11) yes
N3 . C7 . 1.2912(11) yes
N3 . C8 . 1.4889(11) yes
N21 . C22 . 1.4047(13) yes
N21 . C26 . 1.3961(12) yes
C1 . C1 2_766 1.1784(18) yes
C1 . C2 . 1.4459(11) yes
C2 . C3 . 1.3919(12) yes
C3 . C4 . 1.3799(11) yes
C3 . H31 . 0.950 no
C4 . C5 . 1.3968(12) yes
C4 . H41 . 0.950 no
C5 . C6 . 1.3950(11) yes
C5 . C7 . 1.4717(11) yes
C6 . H61 . 0.950 no
C8 . C9 . 1.5266(14) yes
C8 . C10 . 1.5348(16) yes
C8 . C11 . 1.5501(14) yes
C9 . H91 . 0.950 no
C9 . H92 . 0.950 no
C9 . H93 . 0.950 no
C10 . H101 . 0.950 no
C10 . H102 . 0.950 no
C10 . H103 . 0.950 no
C11 . C12 . 1.5224(15) yes
C11 . C13 . 1.5278(14) yes
C12 . H121 . 0.950 no
C12 . H122 . 0.950 no
C12 . H123 . 0.950 no
C13 . H131 . 0.950 no
C13 . H132 . 0.950 no
C13 . H133 . 0.950 no
C21 . C21 2_655 1.1910(18) yes
C21 . C22 . 1.4478(12) yes
C22 . C23 . 1.3296(13) yes
C23 . C24 . 1.3284(12) yes
C23 . H231 . 0.950 no
C24 . C25 . 1.3994(12) yes
C24 . H241 . 0.950 no
C25 . C26 . 1.3882(12) yes
C25 . C27 . 1.4744(12) yes
C26 . H261 . 0.950 no
C27 . N221 . 1.3968(15) yes
C27 . N231 . 1.3152(19) yes
C27 . N222 . 1.369(4) yes
C27 . N232 . 1.207(6) yes
C28 . C29 . 1.5176(15) yes
C28 . C30 . 1.5318(16) yes
C28 . C31 . 1.5618(14) yes
C28 . N231 . 1.487(2) yes
C28 . N232 . 1.558(6) yes
C29 . H291 . 0.950 no
C29 . H292 . 0.950 no
C29 . H293 . 0.950 no
C30 . H301 . 0.950 no
C30 . H302 . 0.950 no
C30 . H303 . 0.950 no
C31 . C32 . 1.5068(16) yes
C31 . C33 . 1.5182(18) yes
C31 . N221 . 1.4672(15) yes
C31 . N222 . 1.575(4) yes
C32 . H321 . 0.950 no
C32 . H322 . 0.950 no
C32 . H323 . 0.950 no
C33 . H331 . 0.950 no
C33 . H332 . 0.950 no
C33 . H333 . 0.950 no
O211 . N221 . 1.2775(15) yes
O211 . O212 . 1.437(5) yes
O211 . N222 . 1.546(6) yes
N221 . O212 . 1.635(5) yes
O212 . N222 . 1.257(6) 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 . C6 . 116.87(8) yes
O1 . N2 . C7 . 126.56(7) yes
O1 . N2 . C11 . 124.17(7) yes
C7 . N2 . C11 . 109.10(7) yes
C7 . N3 . C8 . 107.39(7) yes
C22 . N21 . C26 . 117.73(9) yes
C1 2_766 C1 . C2 . 177.11(13) yes
C1 . C2 . N1 . 116.66(8) yes
C1 . C2 . C3 . 119.92(8) yes
N1 . C2 . C3 . 123.39(7) yes
C2 . C3 . C4 . 118.53(8) yes
C2 . C3 . H31 . 121.3 no
C4 . C3 . H31 . 120.2 no
C3 . C4 . C5 . 119.14(8) yes
C3 . C4 . H41 . 121.4 no
C5 . C4 . H41 . 119.4 no
C4 . C5 . C6 . 117.83(8) yes
C4 . C5 . C7 . 118.61(7) yes
C6 . C5 . C7 . 123.56(8) yes
C5 . C6 . N1 . 124.17(8) yes
C5 . C6 . H61 . 118.1 no
N1 . C6 . H61 . 117.8 no
C5 . C7 . N2 . 122.22(7) yes
C5 . C7 . N3 . 124.13(8) yes
N2 . C7 . N3 . 113.64(7) yes
N3 . C8 . C9 . 109.38(8) yes
N3 . C8 . C10 . 104.77(8) yes
C9 . C8 . C10 . 109.65(9) yes
N3 . C8 . C11 . 105.25(7) yes
C9 . C8 . C11 . 114.33(9) yes
C10 . C8 . C11 . 112.88(9) yes
C8 . C9 . H91 . 109.3 no
C8 . C9 . H92 . 110.0 no
H91 . C9 . H92 . 109.5 no
C8 . C9 . H93 . 109.1 no
H91 . C9 . H93 . 109.5 no
H92 . C9 . H93 . 109.5 no
C8 . C10 . H101 . 109.1 no
C8 . C10 . H102 . 110.5 no
H101 . C10 . H102 . 109.5 no
C8 . C10 . H103 . 108.8 no
H101 . C10 . H103 . 109.5 no
H102 . C10 . H103 . 109.5 no
C8 . C11 . N2 . 98.67(7) yes
C8 . C11 . C12 . 113.96(9) yes
N2 . C11 . C12 . 106.67(8) yes
C8 . C11 . C13 . 116.41(8) yes
N2 . C11 . C13 . 109.92(8) yes
C12 . C11 . C13 . 110.15(9) yes
C11 . C12 . H121 . 110.1 no
C11 . C12 . H122 . 108.8 no
H121 . C12 . H122 . 109.5 no
C11 . C12 . H123 . 109.5 no
H121 . C12 . H123 . 109.5 no
H122 . C12 . H123 . 109.5 no
C11 . C13 . H131 . 109.8 no
C11 . C13 . H132 . 109.0 no
H131 . C13 . H132 . 109.5 no
C11 . C13 . H133 . 109.6 no
H131 . C13 . H133 . 109.5 no
H132 . C13 . H133 . 109.5 no
C21 2_655 C21 . C22 . 178.15(13) yes
C21 . C22 . N21 . 119.80(9) yes
C21 . C22 . C23 . 116.59(8) yes
N21 . C22 . C23 . 123.60(8) yes
C22 . C23 . C24 . 117.71(8) yes
C22 . C23 . H231 . 121.2 no
C24 . C23 . H231 . 121.1 no
C23 . C24 . C25 . 123.83(9) yes
C23 . C24 . H241 . 118.0 no
C25 . C24 . H241 . 118.1 no
C24 . C25 . C26 . 117.99(8) yes
C24 . C25 . C27 . 122.64(8) yes
C26 . C25 . C27 . 119.32(8) yes
N21 . C26 . C25 . 119.13(8) yes
N21 . C26 . H261 . 120.8 no
C25 . C26 . H261 . 120.1 no
C25 . C27 . N221 . 123.81(9) yes
C25 . C27 . N231 . 123.53(11) yes
N221 . C27 . N231 . 112.67(11) yes
C25 . C27 . N222 . 118.33(19) yes
N221 . C27 . N222 . 27.1(2) yes
N231 . C27 . N222 . 111.3(2) yes
C25 . C27 . N232 . 122.9(3) yes
N221 . C27 . N232 . 108.4(3) yes
N231 . C27 . N232 . 23.3(2) yes
N222 . C27 . N232 . 118.7(3) yes
C29 . C28 . C30 . 108.64(9) yes
C29 . C28 . C31 . 113.36(9) yes
C30 . C28 . C31 . 113.94(9) yes
C29 . C28 . N231 . 109.90(11) yes
C30 . C28 . N231 . 104.65(10) yes
C31 . C28 . N231 . 105.91(10) yes
C29 . C28 . N232 . 94.7(2) yes
C30 . C28 . N232 . 122.4(2) yes
C31 . C28 . N232 . 102.4(2) yes
N231 . C28 . N232 . 19.52(16) yes
C28 . C29 . H291 . 110.1 no
C28 . C29 . H292 . 109.9 no
H291 . C29 . H292 . 109.5 no
C28 . C29 . H293 . 108.3 no
H291 . C29 . H293 . 109.5 no
H292 . C29 . H293 . 109.5 no
C28 . C30 . H301 . 110.1 no
C28 . C30 . H302 . 110.0 no
H301 . C30 . H302 . 109.5 no
C28 . C30 . H303 . 108.3 no
H301 . C30 . H303 . 109.5 no
H302 . C30 . H303 . 109.5 no
C28 . C31 . C32 . 116.73(10) yes
C28 . C31 . C33 . 114.89(10) yes
C32 . C31 . C33 . 107.97(12) yes
C28 . C31 . N221 . 98.52(8) yes
C32 . C31 . N221 . 108.29(11) yes
C33 . C31 . N221 . 109.81(11) yes
C28 . C31 . N222 . 98.86(16) yes
C32 . C31 . N222 . 127.4(2) yes
C33 . C31 . N222 . 88.1(2) yes
N221 . C31 . N222 . 24.30(18) yes
C31 . C32 . H321 . 109.9 no
C31 . C32 . H322 . 108.1 no
H321 . C32 . H322 . 109.5 no
C31 . C32 . H323 . 110.4 no
H321 . C32 . H323 . 109.5 no
H322 . C32 . H323 . 109.5 no
C31 . C33 . H331 . 110.0 no
C31 . C33 . H332 . 110.2 no
H331 . C33 . H332 . 109.5 no
C31 . C33 . H333 . 108.2 no
H331 . C33 . H333 . 109.5 no
H332 . C33 . H333 . 109.5 no
N221 . O211 . O212 . 73.78(19) yes
N221 . O211 . N222 . 24.26(14) yes
O212 . O211 . N222 . 49.7(2) yes
C31 . N221 . C27 . 110.35(10) yes
C31 . N221 . O211 . 123.64(11) yes
C27 . N221 . O211 . 125.72(11) yes
C31 . N221 . O212 . 106.19(17) yes
C27 . N221 . O212 . 104.46(18) yes
O211 . N221 . O212 . 57.60(18) yes
C28 . N231 . C27 . 107.06(13) yes
N221 . O212 . O211 . 48.63(16) yes
N221 . O212 . N222 . 21.2(3) yes
O211 . O212 . N222 . 69.7(4) yes
O211 . N222 . C31 . 101.7(3) yes
O211 . N222 . C27 . 109.3(3) yes
C31 . N222 . C27 . 105.8(2) yes
O211 . N222 . O212 . 60.7(3) yes
C31 . N222 . O212 . 122.0(3) yes
C27 . N222 . O212 . 132.1(4) yes
C28 . N232 . C27 . 108.7(4) yes
