# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Cytidine_(Rigaku_Master_fo

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C16 H8 Br2 N2 O2'
_chemical_formula_moiety         'C16 H8 Br2 N2 O2'
_chemical_formula_weight         420.06
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   13.794(7)
_cell_length_b                   4.462(4)
_cell_length_c                   11.963(7)
_cell_angle_alpha                90.0000
_cell_angle_beta                 110.23(4)
_cell_angle_gamma                90.0000
_cell_volume                     690.8(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      14.96
_cell_measurement_theta_max      17.23
_cell_measurement_temperature    298
#------------------------------------------------------------------------------
_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    2.019
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408.00
_exptl_absorpt_coefficient_mu    5.892
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_absorpt_correction_T_min  0.102
_exptl_absorpt_correction_T_max  0.308

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      298
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       ω-2θ
_diffrn_reflns_number            2356
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_theta_max         30.01
_diffrn_reflns_theta_full        30.01
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       8
_diffrn_standards_number         3
_diffrn_standards_interval_count 150
_diffrn_standards_decay_%        -0.665

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2015
_reflns_number_gt                1201
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1328
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_reflns         2015
_refine_ls_number_parameters     116
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0562P)²+0.9432P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.590
_refine_diff_density_min         -0.740
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
Br1 Br 0.44404(4) 0.20426(13) 0.36230(4) 0.0493(2) Uani 1.0 4 d . . .
O1 O 0.0793(3) 1.0089(8) 0.2338(3) 0.0385(7) Uani 1.0 4 d . . .
N1 N 0.0870(3) 0.7284(9) -0.0363(3) 0.0342(8) Uani 1.0 4 d . . .
C1 C 0.3317(4) 0.3641(11) 0.2342(4) 0.0364(10) Uani 1.0 4 d . . .
C2 C 0.2635(4) 0.5601(11) 0.2575(4) 0.0342(9) Uani 1.0 4 d . . .
C3 C 0.3215(4) 0.2761(11) 0.1183(5) 0.0398(10) Uani 1.0 4 d . . .
C4 C 0.1837(3) 0.6697(10) 0.1617(4) 0.0289(8) Uani 1.0 4 d . . .
C5 C 0.2396(4) 0.3870(12) 0.0209(5) 0.0378(10) Uani 1.0 4 d . . .
C6 C 0.1724(3) 0.5851(10) 0.0444(4) 0.0312(9) Uani 1.0 4 d . . .
C7 C 0.0999(4) 0.8783(10) 0.1544(4) 0.0301(9) Uani 1.0 4 d . . .
C8 C 0.0424(3) 0.9115(10) 0.0246(4) 0.0302(9) Uani 1.0 4 d . . .
H1 H 0.257(4) 0.612(11) 0.335(4) 0.031(12) Uiso 1.0 4 d . . .
H2 H 0.372(4) 0.146(10) 0.104(4) 0.023(11) Uiso 1.0 4 d . . .
H3 H 0.219(4) 0.317(11) -0.056(5) 0.033(12) Uiso 1.0 4 d . . .
H4 H 0.069(4) 0.700(11) -0.112(5) 0.039(14) Uiso 1.0 4 d . . .



#==============================================================================
_computing_data_collection       WinAFC
_computing_cell_refinement       WinAFC
_computing_data_reduction        WinAFC
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
Br1 C1 1.902(4) yes . .
O1 C7 1.229(6) yes . .
N1 C6 1.393(5) yes . .
N1 C8 1.373(7) yes . .
C1 C2 1.382(7) yes . .
C1 C3 1.400(7) yes . .
C2 C4 1.376(6) yes . .
C3 C5 1.403(6) yes . .
C4 C6 1.409(6) yes . .
C4 C7 1.463(7) yes . .
C5 C6 1.378(7) yes . .
C7 C8 1.487(5) yes . .
C8 C8 1.364(6) yes . 3_575
N1 H4 0.86(5) no . .
C2 H1 0.99(6) no . .
C3 H2 0.97(5) no . .
C5 H3 0.92(5) no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C6 N1 C8 109.4(4) yes . . .
Br1 C1 C2 119.8(4) yes . . .
Br1 C1 C3 117.9(4) yes . . .
C2 C1 C3 122.4(4) yes . . .
C1 C2 C4 117.4(4) yes . . .
C1 C3 C5 120.0(5) yes . . .
C2 C4 C6 121.1(5) yes . . .
C2 C4 C7 131.6(4) yes . . .
C6 C4 C7 107.3(3) yes . . .
C3 C5 C6 117.5(5) yes . . .
N1 C6 C4 110.1(4) yes . . .
N1 C6 C5 128.3(4) yes . . .
C4 C6 C5 121.6(4) yes . . .
O1 C7 C4 130.1(4) yes . . .
O1 C7 C8 125.3(4) yes . . .
C4 C7 C8 104.6(4) yes . . .
N1 C8 C7 108.6(4) yes . . .
N1 C8 C8 126.2(4) yes . . 3_575
C7 C8 C8 125.2(5) yes . . 3_575
C6 N1 H4 122(4) no . . .
C8 N1 H4 129(4) no . . .
C1 C2 H1 129(3) no . . .
C4 C2 H1 113(3) no . . .
C1 C3 H2 121(3) no . . .
C5 C3 H2 119(3) no . . .
C3 C5 H3 126(3) no . . .
C6 C5 H3 115(4) no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C6 N1 C8 C7 -2.1(5) no . . . .
C6 N1 C8 C8 179.6(4) no . . . 3_575
C8 N1 C6 C4 1.2(5) no . . . .
C8 N1 C6 C5 -178.9(4) no . . . .
Br1 C1 C2 C4 179.9(3) no . . . .
Br1 C1 C3 C5 179.7(3) no . . . .
C2 C1 C3 C5 -0.2(8) no . . . .
C3 C1 C2 C4 -0.2(7) no . . . .
C1 C2 C4 C6 -0.0(7) no . . . .
C1 C2 C4 C7 -179.5(4) no . . . .
C1 C3 C5 C6 0.9(7) no . . . .
C2 C4 C6 N1 -179.3(4) no . . . .
C2 C4 C6 C5 0.8(7) no . . . .
C2 C4 C7 O1 -0.4(9) no . . . .
C2 C4 C7 C8 178.0(5) no . . . .
C6 C4 C7 O1 -179.9(5) no . . . .
C6 C4 C7 C8 -1.5(5) no . . . .
C7 C4 C6 N1 0.3(5) no . . . .
C7 C4 C6 C5 -179.6(4) no . . . .
C3 C5 C6 N1 178.9(5) no . . . .
C3 C5 C6 C4 -1.2(7) no . . . .
O1 C7 C8 N1 -179.2(4) no . . . .
O1 C7 C8 C8 -1.0(8) no . . . 3_575
C4 C7 C8 N1 2.2(5) no . . . .
C4 C7 C8 C8 -179.5(4) no . . . 3_575
N1 C8 C8 N1 -180.0(4) no . . 3_575 3_575
N1 C8 C8 C7 -2.0(8) no . . 3_575 3_575
C7 C8 C8 N1 2.0(8) no . . 3_575 3_575
C7 C8 C8 C7 -180.0(5) no . . 3_575 3_575

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
O1 N1 3.501(6) no . .
O1 N1 2.911(5) no . 3_575
O1 C2 3.169(6) no . .
O1 C6 3.517(6) no . .
O1 C8 2.985(5) no . 3_575
N1 C2 3.596(6) no . .
N1 C7 3.034(6) no . 3_575
C1 C6 2.740(6) no . .
C2 C5 2.842(7) no . .
C3 C4 2.765(7) no . .
C6 C8 3.579(7) no . 3_575
O1 O1 3.241(5) no . 2_545
O1 O1 3.241(5) no . 2_555
O1 N1 2.915(6) no . 4_565
O1 C2 3.476(6) no . 1_565
O1 C4 3.517(6) no . 1_565
O1 C5 3.413(6) no . 4_565
O1 C6 3.511(5) no . 4_565
O1 C7 3.593(7) no . 2_555
N1 O1 2.915(6) no . 4_564
N1 N1 3.480(7) no . 3_565
N1 C5 3.541(7) no . 1_565
N1 C8 3.395(7) no . 3_565
C2 O1 3.476(6) no . 1_545
C3 C4 3.447(7) no . 1_545
C4 O1 3.517(6) no . 1_545
C4 C3 3.447(7) no . 1_565
C5 O1 3.413(6) no . 4_564
C5 N1 3.541(7) no . 1_545
C5 C8 3.462(7) no . 1_545
C6 O1 3.511(5) no . 4_564
C6 C8 3.465(7) no . 1_545
C6 C8 3.560(7) no . 3_565
C7 O1 3.593(7) no . 2_545
C8 N1 3.395(7) no . 3_565
C8 C5 3.462(7) no . 1_565
C8 C6 3.465(7) no . 1_565
C8 C6 3.560(7) no . 3_565
Br1 H1 3.08(5) no . .
Br1 H2 2.91(4) no . .
O1 H1 2.93(5) no . .
O1 H4 2.44(5) no . 3_575
N1 H3 2.66(6) no . .
C1 H3 3.29(5) no . .
C2 H2 3.31(5) no . .
C3 H1 3.37(6) no . .
C4 H3 3.22(6) no . .
C4 H4 3.11(5) no . .
C5 H4 2.72(5) no . .
C6 H1 3.27(5) no . .
C6 H2 3.26(5) no . .
C7 H1 2.75(4) no . .
C7 H4 3.17(6) no . .
C7 H4 2.90(6) no . 3_575
C8 H4 2.75(6) no . 3_575
H2 H3 2.44(6) no . .
H3 H4 2.58(7) no . .
Br1 H2 3.48(5) no . 2_645
Br1 H2 3.12(5) no . 2_655
Br1 H2 3.43(5) no . 4_555
Br1 H3 3.56(7) no . 4_555
O1 H1 3.56(5) no . 1_565
O1 H3 2.70(5) no . 4_565
O1 H4 2.11(6) no . 4_565
N1 H1 3.30(6) no . 4_564
N1 H3 3.25(6) no . 1_565
C1 H3 3.47(6) no . 4_555
C2 H3 3.02(6) no . 4_555
C5 H1 3.21(5) no . 4_554
C5 H1 3.22(5) no . 4_564
C6 H1 3.39(6) no . 4_564
C7 H3 3.55(5) no . 4_565
C7 H4 3.40(5) no . 3_565
C7 H4 2.99(6) no . 4_565
C8 H3 3.43(6) no . 1_565
C8 H4 3.47(6) no . 3_565
H1 O1 3.56(5) no . 1_545
H1 N1 3.30(6) no . 4_565
H1 C5 3.21(5) no . 4_555
H1 C5 3.22(5) no . 4_565
H1 C6 3.39(6) no . 4_565
H1 H2 3.27(6) no . 4_555
H1 H3 2.47(8) no . 4_555
H1 H3 2.99(7) no . 4_565
H1 H4 3.00(8) no . 4_565
H2 Br1 3.12(5) no . 2_645
H2 Br1 3.48(5) no . 2_655
H2 Br1 3.43(5) no . 4_554
H2 H1 3.27(6) no . 4_554
H3 Br1 3.56(7) no . 4_554
H3 O1 2.70(5) no . 4_564
H3 N1 3.25(6) no . 1_545
H3 C1 3.47(6) no . 4_554
H3 C2 3.02(6) no . 4_554
H3 C7 3.55(5) no . 4_564
H3 C8 3.43(6) no . 1_545
H3 H1 2.47(8) no . 4_554
H3 H1 2.99(7) no . 4_564
H3 H4 3.37(7) no . 1_545
H4 O1 2.11(6) no . 4_564
H4 C7 3.40(5) no . 3_565
H4 C7 2.99(6) no . 4_564
H4 C8 3.47(6) no . 3_565
H4 H1 3.00(8) no . 4_564
H4 H3 3.37(7) no . 1_565

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H4 O1 . . 3_575 2.911(5) 0.86(6) 2.44(5) 115(5) no
N1 H4 O1 . . 4_564 2.915(6) 0.86(6) 2.11(5) 154(5) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
_database_code_depnum_ccdc_archive 'CCDC 1002555'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_20130507

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C28 H18 N2 O2'
_chemical_formula_moiety         'C28 H18 N2 O2'
_chemical_formula_weight         414.46
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   21.2805(6)
_cell_length_b                   7.0108(2)
_cell_length_c                   6.5404(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 92.739(2)
_cell_angle_gamma                90.0000
_cell_volume                     974.67(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6056
_cell_measurement_theta_min      4.16
_cell_measurement_theta_max      68.03
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       unknown
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.255
_exptl_crystal_size_mid          0.174
_exptl_crystal_size_min          0.024
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432.00
_exptl_absorpt_coefficient_mu    0.716
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.562
_exptl_absorpt_correction_T_max  0.983

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            10512
_diffrn_reflns_av_R_equivalents  0.1548
_diffrn_reflns_theta_max         68.15
_diffrn_reflns_theta_full        68.18
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             1777
_reflns_number_gt                1020
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0692
_refine_ls_wR_factor_ref         0.2044
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         1777
_refine_ls_number_parameters     145
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1020P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.270
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.06662(9) 1.0315(3) 0.3483(4) 0.0604(7) Uani 1.0 4 d . . .
N1 N 0.06352(11) 0.9808(4) -0.1847(4) 0.0501(8) Uani 1.0 4 d . . .
C1 C 0.03164(12) 0.9997(4) -0.0069(5) 0.0433(8) Uani 1.0 4 d . . .
C2 C 0.07916(12) 1.0172(4) 0.1660(5) 0.0426(8) Uani 1.0 4 d . . .
C3 C 0.12771(12) 0.9850(4) -0.1403(5) 0.0406(8) Uani 1.0 4 d . . .
C4 C 0.13967(12) 1.0106(4) 0.0714(5) 0.0413(8) Uani 1.0 4 d . . .
C5 C 0.17657(13) 0.9639(4) -0.2710(5) 0.0470(8) Uani 1.0 4 d . . .
C6 C 0.20118(12) 1.0157(4) 0.1512(5) 0.0428(8) Uani 1.0 4 d . . .
C7 C 0.23709(13) 0.9686(4) -0.1867(5) 0.0441(8) Uani 1.0 4 d . . .
C8 C 0.25148(12) 0.9943(3) 0.0232(5) 0.0377(7) Uani 1.0 4 d . . .
C9 C 0.31785(12) 0.9960(4) 0.1057(5) 0.0369(7) Uani 1.0 4 d . . .
C10 C 0.33545(12) 1.0974(4) 0.2830(4) 0.0425(8) Uani 1.0 4 d . . .
C11 C 0.36510(11) 0.8964(4) 0.0091(4) 0.0418(7) Uani 1.0 4 d . . .
C12 C 0.39698(12) 1.1013(4) 0.3580(5) 0.0477(8) Uani 1.0 4 d . . .
C13 C 0.42691(12) 0.9021(4) 0.0852(5) 0.0452(8) Uani 1.0 4 d . . .
C14 C 0.44326(13) 1.0045(4) 0.2583(5) 0.0452(8) Uani 1.0 4 d . . .
H1 H 0.0461 0.9682 -0.3053 0.0602 Uiso 1.0 4 calc R . .
H5 H 0.1688 0.9473 -0.4110 0.0564 Uiso 1.0 4 calc R . .
H6 H 0.2090 1.0336 0.2910 0.0514 Uiso 1.0 4 calc R . .
H7 H 0.2702 0.9539 -0.2733 0.0529 Uiso 1.0 4 calc R . .
H10 H 0.3050 1.1636 0.3518 0.0510 Uiso 1.0 4 calc R . .
H11 H 0.3548 0.8255 -0.1079 0.0501 Uiso 1.0 4 calc R . .
H12 H 0.4076 1.1695 0.4767 0.0572 Uiso 1.0 4 calc R . .
H13 H 0.4577 0.8357 0.0181 0.0542 Uiso 1.0 4 calc R . .
H14 H 0.4849 1.0089 0.3081 0.0543 Uiso 1.0 4 calc R . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
O1 C2 1.238(4) yes . .
N1 C1 1.380(4) yes . .
N1 C3 1.383(4) yes . .
C1 C1 1.354(4) yes . 3_575
C1 C2 1.486(4) yes . .
C2 C4 1.456(4) yes . .
C3 C4 1.407(5) yes . .
C3 C5 1.385(5) yes . .
C4 C6 1.386(4) yes . .
C5 C7 1.377(4) yes . .
C6 C8 1.398(4) yes . .
C7 C8 1.404(4) yes . .
C8 C9 1.488(4) yes . .
C9 C10 1.396(4) yes . .
C9 C11 1.400(4) yes . .
C10 C12 1.376(4) yes . .
C11 C13 1.384(4) yes . .
C12 C14 1.384(4) yes . .
C13 C14 1.372(4) yes . .
N1 H1 0.860 no . .
C5 H5 0.930 no . .
C6 H6 0.930 no . .
C7 H7 0.930 no . .
C10 H10 0.930 no . .
C11 H11 0.930 no . .
C12 H12 0.930 no . .
C13 H13 0.930 no . .
C14 H14 0.930 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C1 N1 C3 110.0(3) yes . . .
N1 C1 C1 126.0(3) yes . . 3_575
N1 C1 C2 107.8(3) yes . . .
C1 C1 C2 126.3(3) yes 3_575 . .
O1 C2 C1 124.7(3) yes . . .
O1 C2 C4 130.4(3) yes . . .
C1 C2 C4 104.9(3) yes . . .
N1 C3 C4 109.9(3) yes . . .
N1 C3 C5 129.1(3) yes . . .
C4 C3 C5 121.0(3) yes . . .
C2 C4 C3 107.5(3) yes . . .
C2 C4 C6 132.6(3) yes . . .
C3 C4 C6 119.8(3) yes . . .
C3 C5 C7 117.8(3) yes . . .
C4 C6 C8 120.5(3) yes . . .
C5 C7 C8 123.4(3) yes . . .
C6 C8 C7 117.5(3) yes . . .
C6 C8 C9 121.5(3) yes . . .
C7 C8 C9 121.0(3) yes . . .
C8 C9 C10 121.2(3) yes . . .
C8 C9 C11 121.5(3) yes . . .
C10 C9 C11 117.3(3) yes . . .
C9 C10 C12 121.3(3) yes . . .
C9 C11 C13 120.9(3) yes . . .
C10 C12 C14 120.6(3) yes . . .
C11 C13 C14 120.7(3) yes . . .
C12 C14 C13 119.2(3) yes . . .
C1 N1 H1 125.018 no . . .
C3 N1 H1 125.030 no . . .
C3 C5 H5 121.121 no . . .
C7 C5 H5 121.121 no . . .
C4 C6 H6 119.733 no . . .
C8 C6 H6 119.751 no . . .
C5 C7 H7 118.297 no . . .
C8 C7 H7 118.290 no . . .
C9 C10 H10 119.363 no . . .
C12 C10 H10 119.359 no . . .
C9 C11 H11 119.533 no . . .
C13 C11 H11 119.532 no . . .
C10 C12 H12 119.728 no . . .
C14 C12 H12 119.715 no . . .
C11 C13 H13 119.637 no . . .
C14 C13 H13 119.644 no . . .
C12 C14 H14 120.419 no . . .
C13 C14 H14 120.417 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 N1 C3 C4 -1.0(3) no . . . .
C1 N1 C3 C5 177.4(2) no . . . .
C3 N1 C1 C1 -179.5(2) no . . . 3_575
C3 N1 C1 C2 -0.1(3) no . . . .
N1 C1 C1 N1 -180.0(3) no . . 3_575 3_575
N1 C1 C1 C2 -0.7(4) no . . 3_575 3_575
N1 C1 C2 O1 -178.1(3) no . . . .
N1 C1 C2 C4 1.1(3) no . . . .
C1 C1 C2 O1 1.3(4) no 3_575 . . .
C1 C1 C2 C4 -179.5(3) no 3_575 . . .
C2 C1 C1 N1 0.7(4) no . . 3_575 3_575
C2 C1 C1 C2 180.0(3) no . . 3_575 3_575
O1 C2 C4 C3 177.4(3) no . . . .
O1 C2 C4 C6 0.8(5) no . . . .
C1 C2 C4 C3 -1.7(3) no . . . .
C1 C2 C4 C6 -178.3(3) no . . . .
N1 C3 C4 C2 1.7(3) no . . . .
N1 C3 C4 C6 178.87(19) no . . . .
N1 C3 C5 C7 -178.2(3) no . . . .
C4 C3 C5 C7 0.1(4) no . . . .
C5 C3 C4 C2 -176.9(2) no . . . .
C5 C3 C4 C6 0.3(4) no . . . .
C2 C4 C6 C8 175.8(3) no . . . .
C3 C4 C6 C8 -0.5(4) no . . . .
C3 C5 C7 C8 -0.3(4) no . . . .
C4 C6 C8 C7 0.3(4) no . . . .
C4 C6 C8 C9 -178.95(19) no . . . .
C5 C7 C8 C6 0.1(4) no . . . .
C5 C7 C8 C9 179.4(2) no . . . .
C6 C8 C9 C10 -28.6(4) no . . . .
C6 C8 C9 C11 151.4(3) no . . . .
C7 C8 C9 C10 152.2(3) no . . . .
C7 C8 C9 C11 -27.8(4) no . . . .
C8 C9 C10 C12 -179.1(2) no . . . .
C8 C9 C11 C13 178.8(2) no . . . .
C10 C9 C11 C13 -1.2(4) no . . . .
C11 C9 C10 C12 0.9(4) no . . . .
C9 C10 C12 C14 0.2(4) no . . . .
C9 C11 C13 C14 0.5(4) no . . . .
C10 C12 C14 C13 -1.0(4) no . . . .
C11 C13 C14 C12 0.6(4) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
O1 N1 3.502(4) no . .
O1 N1 2.922(3) no . 3_575
O1 C1 2.993(4) no . 3_575
O1 C3 3.522(4) no . .
O1 C6 3.198(4) no . .
N1 C2 3.045(4) no . 3_575
N1 C6 3.585(4) no . .
C1 C3 3.571(4) no . 3_575
C3 C8 2.796(4) no . .
C4 C7 2.751(4) no . .
C5 C6 2.810(5) no . .
C6 C10 3.000(4) no . .
C7 C11 2.997(4) no . .
C9 C14 2.805(4) no . .
C10 C13 2.753(4) no . .
C11 C12 2.754(4) no . .
O1 O1 3.565(3) no . 3_576
O1 N1 3.078(4) no . 1_556
O1 N1 3.599(3) no . 4_565
O1 N1 3.426(3) no . 4_575
O1 C1 3.509(4) no . 4_575
O1 C3 3.545(4) no . 1_556
O1 C5 3.368(4) no . 1_556
N1 O1 3.078(4) no . 1_554
N1 O1 3.599(3) no . 4_564
N1 O1 3.426(3) no . 4_574
C1 O1 3.509(4) no . 4_574
C3 O1 3.545(4) no . 1_554
C4 C5 3.559(4) no . 4_565
C5 O1 3.368(4) no . 1_554
C5 C4 3.559(4) no . 4_564
C5 C6 3.445(4) no . 4_564
C6 C5 3.445(4) no . 4_565
C9 C10 3.577(4) no . 4_574
C10 C9 3.577(4) no . 4_575
C13 C14 3.590(4) no . 4_564
C14 C13 3.590(4) no . 4_565
O1 H1 2.4007 no . 3_575
O1 H6 3.0716 no . .
N1 H5 2.7528 no . .
C1 H1 2.6976 no . 3_575
C2 H1 3.1478 no . .
C2 H1 2.8587 no . 3_575
C2 H6 2.8469 no . .
C3 H6 3.2562 no . .
C3 H7 3.2010 no . .
C4 H1 3.1077 no . .
C4 H5 3.2743 no . .
C5 H1 2.7760 no . .
C6 H7 3.2316 no . .
C6 H10 2.7204 no . .
C7 H6 3.2412 no . .
C7 H11 2.7251 no . .
C8 H5 3.2856 no . .
C8 H10 2.6627 no . .
C8 H11 2.6747 no . .
C9 H6 2.6772 no . .
C9 H7 2.6504 no . .
C9 H12 3.2506 no . .
C9 H13 3.2572 no . .
C10 H6 2.7299 no . .
C10 H11 3.2314 no . .
C10 H14 3.2370 no . .
C11 H7 2.7017 no . .
C11 H10 3.2310 no . .
C11 H14 3.2359 no . .
C12 H13 3.2174 no . .
C13 H12 3.2159 no . .
C14 H10 3.2316 no . .
C14 H11 3.2286 no . .
H1 H5 2.7370 no . .
H5 H7 2.2985 no . .
H6 H10 2.2544 no . .
H7 H11 2.2451 no . .
H10 H12 2.2935 no . .
H11 H13 2.3028 no . .
H12 H14 2.3164 no . .
H13 H14 2.3027 no . .
O1 H1 2.3698 no . 1_556
O1 H5 2.6878 no . 1_556
C1 H1 3.5438 no . 4_565
C2 H1 3.5784 no . 1_556
C2 H1 3.4824 no . 4_565
C2 H5 3.3205 no . 1_556
C3 H5 3.4742 no . 4_565
C4 H5 3.4411 no . 1_556
C4 H5 3.2700 no . 4_565
C5 H6 3.0185 no . 1_554
C5 H6 3.5754 no . 4_564
C6 H5 3.0156 no . 1_556
C6 H5 3.3394 no . 4_565
C7 H6 3.4695 no . 1_554
C7 H6 3.5727 no . 4_564
C7 H6 3.5426 no . 4_574
C7 H10 2.9614 no . 4_574
C8 H5 3.5972 no . 4_565
C8 H7 3.4279 no . 4_565
C8 H10 2.9036 no . 4_574
C9 H7 3.4177 no . 4_565
C9 H10 2.9130 no . 4_574
C9 H11 3.0111 no . 4_565
C9 H12 3.1639 no . 4_574
C10 H7 3.4275 no . 1_556
C10 H7 3.4519 no . 4_575
C10 H10 3.3179 no . 4_574
C10 H11 3.0725 no . 4_565
C10 H12 3.0552 no . 4_574
C11 H7 3.5233 no . 4_565
C11 H10 3.4760 no . 4_574
C11 H11 2.9658 no . 4_565
C11 H12 3.1844 no . 4_574
C12 H11 3.1345 no . 4_565
C12 H12 2.9847 no . 4_574
C12 H13 3.5615 no . 2_655
C12 H13 3.4671 no . 4_565
C12 H14 3.3402 no . 3_676
C13 H11 3.0368 no . 4_565
C13 H12 3.1092 no . 4_574
C13 H13 3.1664 no . 3_675
C13 H13 3.3241 no . 4_565
C13 H14 3.3886 no . 2_645
C13 H14 3.3149 no . 3_675
C14 H11 3.1331 no . 4_565
C14 H12 3.0102 no . 4_574
C14 H13 3.4174 no . 2_655
C14 H13 3.0549 no . 3_675
C14 H13 2.9360 no . 4_565
C14 H14 3.1579 no . 3_676
H1 O1 2.3698 no . 1_554
H1 C1 3.5438 no . 4_564
H1 C2 3.5784 no . 1_554
H1 C2 3.4824 no . 4_564
H1 H1 3.1701 no . 3_574
H5 O1 2.6878 no . 1_554
H5 C2 3.3205 no . 1_554
H5 C3 3.4742 no . 4_564
H5 C4 3.4411 no . 1_554
H5 C4 3.2700 no . 4_564
H5 C6 3.0156 no . 1_554
H5 C6 3.3394 no . 4_564
H5 C8 3.5972 no . 4_564
H5 H6 2.2494 no . 1_554
H6 C5 3.0185 no . 1_556
H6 C5 3.5754 no . 4_565
H6 C7 3.4695 no . 1_556
H6 C7 3.5727 no . 4_565
H6 C7 3.5426 no . 4_575
H6 H5 2.2494 no . 1_556
H6 H7 3.1255 no . 1_556
H7 C8 3.4279 no . 4_564
H7 C9 3.4177 no . 4_564
H7 C10 3.4275 no . 1_554
H7 C10 3.4519 no . 4_574
H7 C11 3.5233 no . 4_564
H7 H6 3.1255 no . 1_554
H7 H10 2.9829 no . 1_554
H7 H10 2.8906 no . 4_574
H7 H11 3.4997 no . 4_564
H10 C7 2.9614 no . 4_575
H10 C8 2.9036 no . 4_575
H10 C9 2.9130 no . 4_575
H10 C10 3.3179 no . 4_575
H10 C11 3.4760 no . 4_575
H10 H7 2.9829 no . 1_556
H10 H7 2.8906 no . 4_575
H10 H10 3.4875 no . 4_574
H10 H10 3.4875 no . 4_575
H10 H11 3.5948 no . 4_565
H10 H12 3.5583 no . 4_574
H11 C9 3.0111 no . 4_564
H11 C10 3.0725 no . 4_564
H11 C11 2.9658 no . 4_564
H11 C12 3.1345 no . 4_564
H11 C13 3.0368 no . 4_564
H11 C14 3.1331 no . 4_564
H11 H7 3.4997 no . 4_565
H11 H10 3.5948 no . 4_564
H11 H11 3.4372 no . 4_564
H11 H11 3.4372 no . 4_565
H11 H13 3.5441 no . 4_564
H12 C9 3.1639 no . 4_575
H12 C10 3.0552 no . 4_575
H12 C11 3.1844 no . 4_575
H12 C12 2.9847 no . 4_575
H12 C13 3.1092 no . 4_575
H12 C14 3.0102 no . 4_575
H12 H10 3.5583 no . 4_575
H12 H12 3.4596 no . 4_574
H12 H12 3.4596 no . 4_575
H12 H13 3.0942 no . 2_655
H12 H14 2.9109 no . 3_676
H12 H14 3.4861 no . 4_575
H13 C12 3.5615 no . 2_645
H13 C12 3.4671 no . 4_564
H13 C13 3.1664 no . 3_675
H13 C13 3.3241 no . 4_564
H13 C14 3.4174 no . 2_645
H13 C14 3.0549 no . 3_675
H13 C14 2.9360 no . 4_564
H13 H11 3.5441 no . 4_565
H13 H12 3.0942 no . 2_645
H13 H13 2.9408 no . 3_675
H13 H13 3.4840 no . 4_564
H13 H13 3.4840 no . 4_565
H13 H14 2.8109 no . 2_645
H13 H14 2.7353 no . 3_675
H13 H14 2.8521 no . 4_564
H14 C12 3.3402 no . 3_676
H14 C13 3.3886 no . 2_655
H14 C13 3.3149 no . 3_675
H14 C14 3.1579 no . 3_676
H14 H12 2.9109 no . 3_676
H14 H12 3.4861 no . 4_574
H14 H13 2.8109 no . 2_655
H14 H13 2.7353 no . 3_675
H14 H13 2.8521 no . 4_565
H14 H14 2.5639 no . 3_676

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O1 . . 3_575 2.922(3) 0.860 2.401 119.5 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
_database_code_depnum_ccdc_archive 'CCDC 1002556'
