# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
#TrackingRef '- 4d.cif'

#------------------ AUDIT DETAILS -------------------------------------------#

_audit_creation_date             2011-06-09
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_update_record             ?

#==============================================================================
#
# SUBMISSION DETAILS

_publ_contact_author_name        'Jose L. Vicario'

# Name of author for correspondence

_publ_contact_author_address     
;
Departamento de Quimica Organica II, Facultad de Ciencia y Tecnologia,
Universidad del Pais Vasco/Euskal Herriko Unibertsitatea. P.O. Box 644,
48080 Bilbao, Spain
;

# Address of author for correspondence

_publ_contact_author_email       joseluis.vicario@ehu.es
_publ_contact_author_fax         (+34)946012748
_publ_contact_author_phone       (+34)946015454

_publ_contact_letter             
;
Submission dated :?????

Please consider this CIF for submission to the Cambridge Crystallographic
Data Centre. I certify that all authors have seen and approved of this
submission, that all have made significant scientific contributions to the
work reported, and that all share responsibility and accountability for
the results.

This CIF is submitted as part of a journal submission
<Insert Journal details here>

;

#==============================================================================
#
# TITLE AND AUTHOR LIST

_publ_section_title              
; Organocatalytic Enantioselective (3+2) Cycloaddition Using Stable
Azomethine Ylides
;
_publ_section_title_footnote     
; XXX
;

# The loop structure below should contain the names and addresses of all
# authors, in the required order of publication. Repeat as necessary.

loop_
_publ_author_name
_publ_author_address
'Fernandez, Naiara'
;
Departamento de Quimica Organica II, Facultad de Ciencia y Tecnologia,
Universidad del Pais Vasco/Euskal Herriko Unibertsitatea. P.O. Box 644,
48080 Bilbao, Spain
;
'Carrillo, Luisa'
;
Departamento de Quimica Organica II, Facultad de Ciencia y Tecnologia,
Universidad del Pais Vasco/Euskal Herriko Unibertsitatea. P.O. Box 644,
48080 Bilbao, Spain
;
'Vicario, Jose L.'
;
Departamento de Quimica Organica II, Facultad de Ciencia y Tecnologia,
Universidad del Pais Vasco/Euskal Herriko Unibertsitatea. P.O. Box 644,
48080 Bilbao, Spain
;
'Badia, Dolores'
;
Departamento de Quimica Organica II, Facultad de Ciencia y Tecnologia,
Universidad del Pais Vasco/Euskal Herriko Unibertsitatea. P.O. Box 644,
48080 Bilbao, Spain
;
'Reyes, Efraim'
;
Departamento de Quimica Organica II, Facultad de Ciencia y Tecnologia,
Universidad del Pais Vasco/Euskal Herriko Unibertsitatea. P.O. Box 644,
48080 Bilbao, Spain
;

#------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------#

data_nf601a
_database_code_depnum_ccdc_archive 'CCDC 844312'
#TrackingRef '- 4d.cif'

_audit_creation_date             2011-06-09T20:59:46-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         'C21 H15 N3 O1'
_chemical_formula_sum            'C21 H15 N3 O1'
_chemical_formula_weight         325.36
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration ad

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.6234(1)
_cell_length_b                   11.2327(1)
_cell_length_c                   25.1140(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1586.35(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    23141
_cell_measurement_theta_min      3.5169
_cell_measurement_theta_max      76.2115
_cell_measurement_wavelength     1.51184

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       Fragment
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.14
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -2 14 0.0755
0 -4 -13 0.0956
0 7 6 0.0804
4 -1 -1 0.0493
-4 1 -3 0.0771
1 4 -13 0.1544
-2 -3 13 0.057
1 7 -4 0.1262

_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.686
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
;
_exptl_absorpt_correction_T_min  0.744
_exptl_absorpt_correction_T_max  0.999

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Nova (Cu) X-ray micro-source'
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_source_voltage           50
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_radiation_probe          x-ray
_diffrn_detector_area_resol_mean 10.4023
_diffrn_orient_matrix_ub_11      -0.0545177
_diffrn_orient_matrix_ub_12      -0.0287121
_diffrn_orient_matrix_ub_13      -0.0587238
_diffrn_orient_matrix_ub_21      -0.2628174
_diffrn_orient_matrix_ub_22      0.033059
_diffrn_orient_matrix_ub_23      0.0089629
_diffrn_orient_matrix_ub_31      0.0546583
_diffrn_orient_matrix_ub_32      0.1300129
_diffrn_orient_matrix_ub_33      -0.0152626
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0098
_diffrn_reflns_number            32687
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.52
_diffrn_reflns_theta_max         76.41
_diffrn_reflns_theta_full        76.41
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_reflns_number_total             3308
_reflns_number_gt                3267
_reflns_threshold_expression     >2\s(I)
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
1 omega -117.00 -18.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -40.7631 -38.0000 150.0000 99

#__ type_ start__ end____ width___ exp.time_
2 omega 5.00 31.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 40.7631 -125.0000 -60.0000 26

#__ type_ start__ end____ width___ exp.time_
3 omega 11.00 115.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 40.7631 77.0000 90.0000 104

#__ type_ start__ end____ width___ exp.time_
4 omega 35.00 144.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 -77.0000 120.0000 109

#__ type_ start__ end____ width___ exp.time_
5 omega 44.00 69.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 -45.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
6 omega 108.00 157.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 111.0000 150.0000 49

#__ type_ start__ end____ width___ exp.time_
7 omega 40.00 69.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 -45.0000 -180.0000 29

#__ type_ start__ end____ width___ exp.time_
8 omega 39.00 71.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 -111.0000 -148.0000 32

#__ type_ start__ end____ width___ exp.time_
9 omega 75.00 104.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 -106.0000 139.0000 29

#__ type_ start__ end____ width___ exp.time_
10 omega 79.00 135.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 111.0000 30.0000 56

#__ type_ start__ end____ width___ exp.time_
11 omega 89.00 139.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 111.0000 125.0000 50

#__ type_ start__ end____ width___ exp.time_
12 omega 82.00 110.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 111.0000 -90.0000 28

#__ type_ start__ end____ width___ exp.time_
13 omega 113.00 146.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 111.0000 -90.0000 33

#__ type_ start__ end____ width___ exp.time_
14 omega 38.00 64.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 -106.0000 139.0000 26

#__ type_ start__ end____ width___ exp.time_
15 omega 97.00 147.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 77.0000 -90.0000 50

#__ type_ start__ end____ width___ exp.time_
16 omega 80.00 105.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 77.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
17 omega 86.00 119.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 111.0000 90.0000 33

#__ type_ start__ end____ width___ exp.time_
18 omega -55.00 22.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -40.7631 38.0000 90.0000 77

#__ type_ start__ end____ width___ exp.time_
19 omega -89.00 -6.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -40.7631 125.0000 -90.0000 83

#__ type_ start__ end____ width___ exp.time_
20 omega -52.00 -8.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -40.7631 -77.0000 90.0000 44

#__ type_ start__ end____ width___ exp.time_
21 omega -49.00 -10.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -40.7631 -77.0000 -150.0000 39

#__ type_ start__ end____ width___ exp.time_
22 omega -32.00 -7.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -40.7631 -77.0000 120.0000 25

#__ type_ start__ end____ width___ exp.time_
23 omega -115.00 -89.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -40.7631 -77.0000 90.0000 26

#__ type_ start__ end____ width___ exp.time_
24 omega -111.00 -9.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -40.7631 -77.0000 0.0000 102

#__ type_ start__ end____ width___ exp.time_
25 omega -111.00 -11.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -40.7631 -77.0000 -60.0000 100

#__ type_ start__ end____ width___ exp.time_
26 omega -21.00 40.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 40.7631 -38.0000 -180.0000 61

#__ type_ start__ end____ width___ exp.time_
27 omega 4.00 91.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 40.7631 -125.0000 -180.0000 87

#__ type_ start__ end____ width___ exp.time_
28 omega -76.00 -50.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -83.0000 -72.0000 179.0000 26

#__ type_ start__ end____ width___ exp.time_
29 omega -77.00 -51.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -83.0000 -70.0000 -145.0000 26

#__ type_ start__ end____ width___ exp.time_
30 omega -75.00 -49.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -83.0000 -77.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
31 omega -76.00 -50.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -83.0000 -76.0000 98.0000 26

#__ type_ start__ end____ width___ exp.time_
32 omega -77.00 -51.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -83.0000 -77.0000 -60.0000 26

#__ type_ start__ end____ width___ exp.time_
33 omega -76.00 -50.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -83.0000 -72.0000 129.0000 26

#__ type_ start__ end____ width___ exp.time_
34 omega -77.00 -51.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -83.0000 -75.0000 173.0000 26

#__ type_ start__ end____ width___ exp.time_
35 omega -77.00 -51.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -83.0000 -69.0000 110.0000 26

#__ type_ start__ end____ width___ exp.time_
36 omega -76.00 -50.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -83.0000 -77.0000 30.0000 26

#__ type_ start__ end____ width___ exp.time_
37 omega -75.00 -49.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -83.0000 -77.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
38 omega -76.00 -51.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -83.0000 -70.0000 27.0000 25

#__ type_ start__ end____ width___ exp.time_
39 omega -75.00 -50.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -83.0000 -73.0000 65.0000 25

#__ type_ start__ end____ width___ exp.time_
40 omega -75.00 -49.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -83.0000 -77.0000 60.0000 26

#__ type_ start__ end____ width___ exp.time_
41 omega -76.00 -50.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -83.0000 -72.0000 5.0000 26

#__ type_ start__ end____ width___ exp.time_
42 omega -76.00 -50.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -83.0000 -77.0000 0.0000 26

#__ type_ start__ end____ width___ exp.time_
43 omega -77.00 -51.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -83.0000 -73.0000 -108.0000 26

#__ type_ start__ end____ width___ exp.time_
44 omega -75.00 -49.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -83.0000 -77.0000 -80.0000 26

#__ type_ start__ end____ width___ exp.time_
45 omega -77.00 -51.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -83.0000 -71.0000 -53.0000 26

#__ type_ start__ end____ width___ exp.time_
46 omega -74.00 -49.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -83.0000 -77.0000 -30.0000 25

#__ type_ start__ end____ width___ exp.time_
47 omega -74.00 -49.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -83.0000 -77.0000 150.0000 25

#__ type_ start__ end____ width___ exp.time_
48 omega 79.00 110.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 111.0000 -150.0000 31

#__ type_ start__ end____ width___ exp.time_
49 omega 117.00 157.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 77.0000 120.0000 40

#__ type_ start__ end____ width___ exp.time_
50 omega 45.00 115.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 -111.0000 19.0000 70

#__ type_ start__ end____ width___ exp.time_
51 omega 79.00 105.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 77.0000 120.0000 26

#__ type_ start__ end____ width___ exp.time_
52 omega 121.00 147.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 -77.0000 -90.0000 26

#__ type_ start__ end____ width___ exp.time_
53 omega 80.00 157.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 77.0000 0.0000 77

#__ type_ start__ end____ width___ exp.time_
54 omega 81.00 119.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 -121.0000 -27.0000 38

#__ type_ start__ end____ width___ exp.time_
55 omega 119.00 150.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 77.0000 -60.0000 31

#__ type_ start__ end____ width___ exp.time_
56 omega 79.00 104.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 77.0000 -60.0000 25

#__ type_ start__ end____ width___ exp.time_
57 omega 39.00 64.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 -121.0000 -27.0000 25

#__ type_ start__ end____ width___ exp.time_
58 omega 119.00 158.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 77.0000 -120.0000 39

#__ type_ start__ end____ width___ exp.time_
59 omega 85.00 125.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 45.0000 -150.0000 40

#__ type_ start__ end____ width___ exp.time_
60 omega 126.00 152.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 -15.0000 120.0000 26

#__ type_ start__ end____ width___ exp.time_
61 omega 79.00 105.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 77.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
62 omega 30.00 102.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 -15.0000 120.0000 72

#__ type_ start__ end____ width___ exp.time_
63 omega 79.00 105.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 77.0000 150.0000 26

#__ type_ start__ end____ width___ exp.time_
64 omega 48.00 74.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 -45.0000 0.0000 26

#__ type_ start__ end____ width___ exp.time_
65 omega 79.00 143.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 77.0000 30.0000 64

#__ type_ start__ end____ width___ exp.time_
66 omega 36.00 62.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 -108.0000 160.0000 26

#__ type_ start__ end____ width___ exp.time_
67 omega 89.00 114.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 -108.0000 160.0000 25

#__ type_ start__ end____ width___ exp.time_
68 omega 108.00 134.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 -77.0000 150.0000 26

#__ type_ start__ end____ width___ exp.time_
69 omega 42.00 68.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 -77.0000 150.0000 26

#__ type_ start__ end____ width___ exp.time_
70 omega 34.00 61.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 -77.0000 -90.0000 27

#__ type_ start__ end____ width___ exp.time_
71 omega 78.00 104.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 -77.0000 -90.0000 26

#__ type_ start__ end____ width___ exp.time_
72 omega 80.00 158.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 77.0000 90.0000 78

#__ type_ start__ end____ width___ exp.time_
73 omega 80.00 106.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 77.0000 -30.0000 26

#__ type_ start__ end____ width___ exp.time_
74 omega 86.00 133.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 45.0000 90.0000 47

#__ type_ start__ end____ width___ exp.time_
75 omega 48.00 76.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 -45.0000 -90.0000 28

#__ type_ start__ end____ width___ exp.time_
76 omega 79.00 158.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 111.0000 -180.0000 79

#__ type_ start__ end____ width___ exp.time_
77 omega 123.00 153.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 77.0000 -150.0000 30

#__ type_ start__ end____ width___ exp.time_
78 omega 79.00 105.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 77.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
79 omega 86.00 154.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 45.0000 0.0000 68

#__ type_ start__ end____ width___ exp.time_
80 omega 39.00 70.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 -77.0000 0.0000 31

#__ type_ start__ end____ width___ exp.time_
81 omega 79.00 105.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 77.0000 60.0000 26

#__ type_ start__ end____ width___ exp.time_
82 omega 93.00 147.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 -77.0000 -180.0000 54

#__ type_ start__ end____ width___ exp.time_
83 omega 36.00 70.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 -77.0000 -180.0000 34

#__ type_ start__ end____ width___ exp.time_
84 omega 79.00 105.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 77.0000 -90.0000 26

#__ type_ start__ end____ width___ exp.time_
85 omega 82.00 122.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 -77.0000 0.0000 40

#__ type_ start__ end____ width___ exp.time_
86 omega 128.00 154.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 113.0000 111.0000 -150.0000 26

;

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_cell_refinement       'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_data_reduction        'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_structure_solution    'SIR92 (Altomare et al, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Diamond v.3.2f (Crystal Impact GbR, 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_publ_section_references         
;
Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993)
<i>J. Appl. Cryst.</i> <b>26</b>, 343--350.

Branderburg, K. (2010), <i>Diamond</i>, Crystal Impact GbR, Bonn, Germany

Oxford Diffraction (2010). <i>CrysAlisPro</i>. Oxford Diffraction Ltd,
Abingdon, Oxfordshire, England.

Farrugia, L. J. (1999). <i>J. Appl. Cryst.</i> <b>32</b>, 837--838.

Sheldrick, G. M. (2008). <i>Acta Cryst.</i> A<b>64</b>, 112--122.
;

#----------------------------------------------------------------------------#
# STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0313P)^2^+0.3553P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_coef       0.0025(3)
_refine_ls_number_reflns         3308
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0248
_refine_ls_wR_factor_ref         0.063
_refine_ls_wR_factor_gt          0.0627
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
Since the crystal structure contains no heavy atoms, the data collection was
done very carefully in order to determine the absolute structure:
low temperature; 99% Friedel pair coverage; and a very big redundancy
(16.9 for Pmmm point group, and 10.0 for P222).
Analysis of the absolute structure using likelihood methods
(Hooft, Straver & Spek, 2008) was performed using PLATON (Spek, 2011).
The results indicated that the absolute structure had been correctly
assigned. The method calculated that the probability that the structure
is inverted is smaller than 10-114. The absolute structure parameter y
(Hooft, Straver & Spek, 2008) was calculated using PLATON (Spek,
2010). The resulting value was y=-0.02(4), indicate that the absolute
structure has very probably been determined correctly.

Flack, H. D. (1983), Acta Cryst. A39, 876-881
Flack & G. Bernardinelli, Acta Cryst. 1999, A55, 908-915;
H. D. Flack & G. Bernardinelli, J. Appl. Cryst. 2000, 33, 1143-1148.

R. W. W. Hooft, L. H. Straver & A. L. Spek, J. Appl. Cryst. 2008, 41, 96-103
A. L. Spek (2010) PLATON, Utrecht, The Netherlands;
A. L. Spek, J. Appl. Cryst. 2003, 36, 7-13
A. L. Thompson & D. J. Watkin, Tetrahedron: Asymmetry 2009, 20, 712--717

;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.03

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.64156(19) 0.19772(9) 0.09245(4) 0.0155(2) Uani 1 1 d . . .
H1 H 0.5154 0.2357 0.0701 0.019 Uiso 1 1 calc R . .
C2 C 0.68306(19) 0.27679(9) 0.14226(4) 0.0157(2) Uani 1 1 d . . .
H2 H 0.8552 0.271 0.1519 0.019 Uiso 1 1 calc R . .
C3 C 0.53513(19) 0.21177(9) 0.18768(4) 0.0160(2) Uani 1 1 d . . .
C5 C 0.2762(2) 0.03289(9) 0.18752(4) 0.0189(2) Uani 1 1 d . . .
H5 H 0.254 0.0397 0.2249 0.023 Uiso 1 1 calc R . .
C6 C 0.1839(2) -0.05942(10) 0.16099(4) 0.0204(2) Uani 1 1 d . . .
H6 H 0.1006 -0.1201 0.1796 0.024 Uiso 1 1 calc R . .
C7 C 0.0670(2) -0.13874(10) 0.07158(4) 0.0210(2) Uani 1 1 d . . .
H7 H -0.048 -0.1885 0.0881 0.025 Uiso 1 1 calc R . .
C8 C 0.0887(2) -0.13889(10) 0.01651(4) 0.0223(2) Uani 1 1 d . . .
H8 H -0.0106 -0.1887 -0.0045 0.027 Uiso 1 1 calc R . .
C9 C 0.2565(2) -0.06585(10) -0.00786(4) 0.0212(2) Uani 1 1 d . . .
H9 H 0.2712 -0.0654 -0.0455 0.025 Uiso 1 1 calc R . .
C10 C 0.4025(2) 0.00647(10) 0.02300(4) 0.0189(2) Uani 1 1 d . . .
H10 H 0.5167 0.0562 0.0062 0.023 Uiso 1 1 calc R . .
C11 C 0.54435(18) 0.07925(9) 0.11392(4) 0.0157(2) Uani 1 1 d . . .
H11 H 0.6794 0.0284 0.1264 0.019 Uiso 1 1 calc R . .
C12 C 0.2119(2) -0.06634(9) 0.10310(4) 0.0174(2) Uani 1 1 d . . .
C13 C 0.38295(19) 0.00681(9) 0.07812(4) 0.0158(2) Uani 1 1 d . . .
C14 C 0.86454(19) 0.18555(10) 0.05893(4) 0.0191(2) Uani 1 1 d . . .
H14 H 0.8818 0.1159 0.0378 0.023 Uiso 1 1 calc R . .
C15 C 0.62207(19) 0.40770(9) 0.13681(4) 0.0154(2) Uani 1 1 d . . .
C16 C 0.41019(19) 0.44541(9) 0.11306(4) 0.0183(2) Uani 1 1 d . . .
H16 H 0.3037 0.3886 0.0984 0.022 Uiso 1 1 calc R . .
C17 C 0.35503(19) 0.56609(10) 0.11093(4) 0.0205(2) Uani 1 1 d . . .
H17 H 0.2111 0.5913 0.0947 0.025 Uiso 1 1 calc R . .
C18 C 0.5089(2) 0.64962(10) 0.13241(4) 0.0203(2) Uani 1 1 d . . .
H18 H 0.4707 0.7319 0.1308 0.024 Uiso 1 1 calc R . .
C19 C 0.7187(2) 0.61282(10) 0.15627(4) 0.0190(2) Uani 1 1 d . . .
H19 H 0.8243 0.67 0.1711 0.023 Uiso 1 1 calc R . .
C20 C 0.77491(19) 0.49213(10) 0.15856(4) 0.0166(2) Uani 1 1 d . . .
H20 H 0.9186 0.4673 0.1751 0.02 Uiso 1 1 calc R . .
C21 C 0.3642(2) 0.28913(10) 0.21634(4) 0.0185(2) Uani 1 1 d . . .
C22 C 0.7023(2) 0.16391(10) 0.22873(4) 0.0183(2) Uani 1 1 d . . .
N1 N 0.2264(2) 0.34275(9) 0.23969(4) 0.0281(2) Uani 1 1 d . . .
N2 N 0.83045(19) 0.12686(10) 0.26000(4) 0.0262(2) Uani 1 1 d . . .
N4 N 0.40569(16) 0.11929(8) 0.15982(3) 0.01647(19) Uani 1 1 d . . .
O1 O 1.02024(15) 0.25817(7) 0.05735(3) 0.02621(19) Uani 1 1 d . . .

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
C1 0.0165(5) 0.0142(5) 0.0159(5) 0.0004(4) -0.0001(4) -0.0007(4)
C2 0.0152(5) 0.0164(5) 0.0156(4) 0.0003(4) -0.0008(4) -0.0001(4)
C3 0.0168(5) 0.0160(5) 0.0151(4) 0.0006(4) -0.0003(4) 0.0004(4)
C5 0.0203(5) 0.0204(5) 0.0160(5) 0.0025(4) 0.0029(4) -0.0002(4)
C6 0.0208(5) 0.0195(5) 0.0208(5) 0.0044(4) 0.0020(4) -0.0029(4)
C7 0.0203(5) 0.0170(5) 0.0257(5) 0.0016(4) 0.0001(4) -0.0025(4)
C8 0.0230(6) 0.0187(5) 0.0252(5) -0.0020(4) -0.0047(4) -0.0033(4)
C9 0.0249(6) 0.0212(5) 0.0177(5) -0.0008(4) -0.0023(4) 0.0002(5)
C10 0.0191(5) 0.0183(5) 0.0194(5) 0.0005(4) 0.0000(4) -0.0004(4)
C11 0.0158(5) 0.0162(5) 0.0151(4) 0.0006(4) 0.0006(4) -0.0002(4)
C12 0.0181(5) 0.0139(5) 0.0201(5) 0.0023(4) -0.0007(4) 0.0010(4)
C13 0.0154(5) 0.0134(4) 0.0187(5) -0.0001(4) -0.0014(4) 0.0010(4)
C14 0.0199(5) 0.0182(5) 0.0192(5) 0.0000(4) 0.0021(4) -0.0019(4)
C15 0.0171(5) 0.0159(5) 0.0133(4) 0.0006(4) 0.0019(4) -0.0003(4)
C16 0.0165(5) 0.0187(5) 0.0197(5) 0.0008(4) 0.0001(4) -0.0015(4)
C17 0.0173(5) 0.0233(5) 0.0209(5) 0.0040(4) 0.0015(4) 0.0033(4)
C18 0.0251(6) 0.0162(5) 0.0195(5) 0.0008(4) 0.0051(4) 0.0046(4)
C19 0.0238(5) 0.0169(5) 0.0162(5) -0.0024(4) 0.0018(4) -0.0023(4)
C20 0.0166(5) 0.0196(5) 0.0137(4) 0.0008(4) -0.0003(4) 0.0008(4)
C21 0.0215(5) 0.0166(5) 0.0173(5) 0.0018(4) 0.0013(4) -0.0006(4)
C22 0.0191(5) 0.0188(5) 0.0169(5) -0.0001(4) 0.0018(4) -0.0005(4)
N1 0.0315(6) 0.0235(5) 0.0293(5) 0.0014(4) 0.0088(4) 0.0038(5)
N2 0.0239(5) 0.0325(5) 0.0223(5) 0.0054(4) -0.0021(4) 0.0015(4)
N4 0.0191(4) 0.0160(4) 0.0143(4) -0.0009(3) 0.0008(3) -0.0028(4)
O1 0.0216(4) 0.0262(4) 0.0308(4) -0.0021(3) 0.0033(4) -0.0053(3)

#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C14 1.5165(15) . ?
C1 C11 1.5364(13) . ?
C1 C2 1.5519(14) . ?
C1 H1 1 . ?
C2 C15 1.5161(14) . ?
C2 C3 1.5895(14) . ?
C2 H2 1 . ?
C3 N4 1.4487(13) . ?
C3 C21 1.4823(14) . ?
C3 C22 1.4950(14) . ?
C5 C6 1.3373(16) . ?
C5 N4 1.3985(13) . ?
C5 H5 0.95 . ?
C6 C12 1.4646(14) . ?
C6 H6 0.95 . ?
C7 C8 1.3886(16) . ?
C7 C12 1.3971(15) . ?
C7 H7 0.95 . ?
C8 C9 1.3919(16) . ?
C8 H8 0.95 . ?
C9 C10 1.3908(15) . ?
C9 H9 0.95 . ?
C10 C13 1.3887(14) . ?
C10 H10 0.95 . ?
C11 N4 1.4626(13) . ?
C11 C13 1.5147(14) . ?
C11 H11 1 . ?
C12 C13 1.4119(14) . ?
C14 O1 1.1973(14) . ?
C14 H14 0.95 . ?
C15 C20 1.3916(15) . ?
C15 C16 1.3981(15) . ?
C16 C17 1.3917(15) . ?
C16 H16 0.95 . ?
C17 C18 1.3856(16) . ?
C17 H17 0.95 . ?
C18 C19 1.3863(16) . ?
C18 H18 0.95 . ?
C19 C20 1.3931(15) . ?
C19 H19 0.95 . ?
C20 H20 0.95 . ?
C21 N1 1.1434(15) . ?
C22 N2 1.1442(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 C1 C11 114.27(9) . . ?
C14 C1 C2 112.01(9) . . ?
C11 C1 C2 105.44(8) . . ?
C14 C1 H1 108.3 . . ?
C11 C1 H1 108.3 . . ?
C2 C1 H1 108.3 . . ?
C15 C2 C1 116.63(8) . . ?
C15 C2 C3 113.08(8) . . ?
C1 C2 C3 103.70(8) . . ?
C15 C2 H2 107.7 . . ?
C1 C2 H2 107.7 . . ?
C3 C2 H2 107.7 . . ?
N4 C3 C21 109.20(9) . . ?
N4 C3 C22 113.02(9) . . ?
C21 C3 C22 106.49(8) . . ?
N4 C3 C2 104.23(8) . . ?
C21 C3 C2 114.74(8) . . ?
C22 C3 C2 109.33(8) . . ?
C6 C5 N4 119.50(9) . . ?
C6 C5 H5 120.3 . . ?
N4 C5 H5 120.3 . . ?
C5 C6 C12 119.60(10) . . ?
C5 C6 H6 120.2 . . ?
C12 C6 H6 120.2 . . ?
C8 C7 C12 120.91(10) . . ?
C8 C7 H7 119.5 . . ?
C12 C7 H7 119.5 . . ?
C7 C8 C9 119.78(10) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C10 C9 C8 119.96(10) . . ?
C10 C9 H9 120 . . ?
C8 C9 H9 120 . . ?
C13 C10 C9 120.69(10) . . ?
C13 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
N4 C11 C13 108.27(8) . . ?
N4 C11 C1 101.54(8) . . ?
C13 C11 C1 118.04(8) . . ?
N4 C11 H11 109.5 . . ?
C13 C11 H11 109.5 . . ?
C1 C11 H11 109.5 . . ?
C7 C12 C13 118.98(10) . . ?
C7 C12 C6 122.04(10) . . ?
C13 C12 C6 118.91(10) . . ?
C10 C13 C12 119.67(10) . . ?
C10 C13 C11 123.09(10) . . ?
C12 C13 C11 117.20(9) . . ?
O1 C14 C1 124.17(10) . . ?
O1 C14 H14 117.9 . . ?
C1 C14 H14 117.9 . . ?
C20 C15 C16 119.16(10) . . ?
C20 C15 C2 119.07(9) . . ?
C16 C15 C2 121.68(9) . . ?
C17 C16 C15 120.10(10) . . ?
C17 C16 H16 120 . . ?
C15 C16 H16 120 . . ?
C18 C17 C16 120.36(10) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 119.85(10) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C18 C19 C20 120.07(10) . . ?
C18 C19 H19 120 . . ?
C20 C19 H19 120 . . ?
C15 C20 C19 120.45(10) . . ?
C15 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
N1 C21 C3 175.90(12) . . ?
N2 C22 C3 179.70(13) . . ?
C5 N4 C3 121.27(8) . . ?
C5 N4 C11 117.14(8) . . ?
C3 N4 C11 109.47(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 C1 C2 C15 93.89(11) . . . . ?
C11 C1 C2 C15 -141.24(9) . . . . ?
C14 C1 C2 C3 -141.10(9) . . . . ?
C11 C1 C2 C3 -16.24(10) . . . . ?
C15 C2 C3 N4 119.70(9) . . . . ?
C1 C2 C3 N4 -7.56(10) . . . . ?
C15 C2 C3 C21 0.33(12) . . . . ?
C1 C2 C3 C21 -126.93(9) . . . . ?
C15 C2 C3 C22 -119.20(9) . . . . ?
C1 C2 C3 C22 113.54(9) . . . . ?
N4 C5 C6 C12 -2.31(17) . . . . ?
C12 C7 C8 C9 -0.18(17) . . . . ?
C7 C8 C9 C10 0.35(17) . . . . ?
C8 C9 C10 C13 -0.02(17) . . . . ?
C14 C1 C11 N4 157.28(8) . . . . ?
C2 C1 C11 N4 33.84(10) . . . . ?
C14 C1 C11 C13 -84.60(12) . . . . ?
C2 C1 C11 C13 151.96(9) . . . . ?
C8 C7 C12 C13 -0.31(16) . . . . ?
C8 C7 C12 C6 176.51(11) . . . . ?
C5 C6 C12 C7 -161.24(11) . . . . ?
C5 C6 C12 C13 15.58(16) . . . . ?
C9 C10 C13 C12 -0.48(16) . . . . ?
C9 C10 C13 C11 177.09(10) . . . . ?
C7 C12 C13 C10 0.63(15) . . . . ?
C6 C12 C13 C10 -176.28(10) . . . . ?
C7 C12 C13 C11 -177.07(9) . . . . ?
C6 C12 C13 C11 6.01(14) . . . . ?
N4 C11 C13 C10 145.73(10) . . . . ?
C1 C11 C13 C10 31.24(14) . . . . ?
N4 C11 C13 C12 -36.65(12) . . . . ?
C1 C11 C13 C12 -151.14(9) . . . . ?
C11 C1 C14 O1 -146.78(11) . . . . ?
C2 C1 C14 O1 -26.96(15) . . . . ?
C1 C2 C15 C20 -138.10(10) . . . . ?
C3 C2 C15 C20 101.78(11) . . . . ?
C1 C2 C15 C16 45.41(14) . . . . ?
C3 C2 C15 C16 -74.70(12) . . . . ?
C20 C15 C16 C17 0.57(15) . . . . ?
C2 C15 C16 C17 177.05(10) . . . . ?
C15 C16 C17 C18 -0.20(16) . . . . ?
C16 C17 C18 C19 -0.14(16) . . . . ?
C17 C18 C19 C20 0.11(16) . . . . ?
C16 C15 C20 C19 -0.60(15) . . . . ?
C2 C15 C20 C19 -177.17(10) . . . . ?
C18 C19 C20 C15 0.27(16) . . . . ?
C6 C5 N4 C3 -171.66(10) . . . . ?
C6 C5 N4 C11 -33.12(15) . . . . ?
C21 C3 N4 C5 -64.84(12) . . . . ?
C22 C3 N4 C5 53.49(13) . . . . ?
C2 C3 N4 C5 172.09(9) . . . . ?
C21 C3 N4 C11 153.83(8) . . . . ?
C22 C3 N4 C11 -87.84(10) . . . . ?
C2 C3 N4 C11 30.76(10) . . . . ?
C13 C11 N4 C5 50.93(12) . . . . ?
C1 C11 N4 C5 175.87(9) . . . . ?
C13 C11 N4 C3 -165.95(8) . . . . ?
C1 C11 N4 C3 -41.01(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
C16 H16 O1 0.9500 2.4000 3.3451(13) 175.00 1_455 yes

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF