# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_ord121
_audit_creation_date             2013-11-11
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_chemical_formula_moiety         'C7 H7 N O2'
_chemical_formula_sum            'C7 H7 N O2'
_chemical_formula_weight         137.14
_chemical_oxdiff_formula         C7N1H7O2
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
O 0.01158 0.00611 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
N 0.00653 0.00323 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_cell_length_a                   18.5620(11)
_cell_length_b                   3.7320(2)
_cell_length_c                   18.5680(12)
_cell_angle_alpha                90
_cell_angle_beta                 93.993(6)
_cell_angle_gamma                90
_cell_volume                     1283.14(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1957
_cell_measurement_temperature    101.15(10)
_cell_measurement_theta_max      28.3343
_cell_measurement_theta_min      2.9947
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.4197
_exptl_crystal_F_000             576.3315
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            4677
_diffrn_reflns_theta_full        25.000000
_diffrn_reflns_theta_max         28.40
_diffrn_reflns_theta_min         3.00
_diffrn_ambient_temperature      101.15(10)
_diffrn_detector_area_resol_mean 8.3367
_diffrn_measured_fraction_theta_full 0.998245
_diffrn_measured_fraction_theta_max 0.896108
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -22.00   69.00   1.0000    2.3200
omega____ theta____ kappa____ phi______ frames
    -       22.6371  -99.0000   60.0000 91

#__ type_ start__ end____ width___ exp.time_
  2 omega   16.00  114.00   1.0000    2.3200
omega____ theta____ kappa____ phi______ frames
    -       22.6371   57.0000 -180.0000 98

#__ type_ start__ end____ width___ exp.time_
  3 omega  -75.00  -40.00   1.0000    2.3200
omega____ theta____ kappa____ phi______ frames
    -       22.6371  -77.0000 -180.0000 35
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0306476000
_diffrn_orient_matrix_UB_12      -0.1139524000
_diffrn_orient_matrix_UB_13      -0.0017540000
_diffrn_orient_matrix_UB_21      -0.0196687000
_diffrn_orient_matrix_UB_22      0.1285345000
_diffrn_orient_matrix_UB_23      -0.0215010000
_diffrn_orient_matrix_UB_31      0.0119201000
_diffrn_orient_matrix_UB_32      -0.0812797000
_diffrn_orient_matrix_UB_33      -0.0316253000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              16
_reflns_limit_h_min              -24
_reflns_limit_k_max              4
_reflns_limit_k_min              0
_reflns_limit_l_max              23
_reflns_limit_l_min              -15
_reflns_number_gt                2177
_reflns_number_total             2855
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution    
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         0.394886
_refine_diff_density_min         -0.358696
_refine_diff_density_rms         0.087287
_refine_ls_d_res_high            0.747240
_refine_ls_d_res_low             6.788401
_refine_ls_goodness_of_fit_ref   1.072681
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    12
_refine_ls_number_parameters     214
_refine_ls_number_reflns         2855
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.072612
_refine_ls_R_factor_gt           0.051566
_refine_ls_restrained_S_all      1.072681
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0438P)²+1.4425P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.134828
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_refinement_flags_posn
C6 C 0.14860(11) 0.4691(6) 0.36187(11) 0.0175(4) Uani 1.000000 .
C7 C 0.66925(11) -0.0184(6) 0.28257(11) 0.0193(5) Uani 1.000000 .
H7 H 0.71381(11) -0.1330(6) 0.28407(11) 0.0232(6) Uiso 1.000000 R
C8 C 0.27927(11) 0.4746(6) 0.36354(11) 0.0184(5) Uani 1.000000 .
N9 N 0.66740(11) 0.0148(6) 0.15245(11) 0.0267(5) Uani 1.000000 .
C10 C 0.15213(11) 0.2941(6) 0.42867(11) 0.0159(4) Uani 1.000000 .
C11 C 0.57107(11) 0.2318(6) 0.34520(11) 0.0162(4) Uani 1.000000 .
C12 C 0.63785(11) 0.0569(6) 0.34615(11) 0.0176(4) Uani 1.000000 .
H12 H 0.66130(11) -0.0093(6) 0.39003(11) 0.0212(5) Uiso 1.000000 R
C13 C 0.28251(11) 0.3013(6) 0.43082(11) 0.0187(5) Uani 1.000000 .
C14 C 0.53631(11) 0.3221(6) 0.27842(11) 0.0186(5) Uani 1.000000 .
H14 H 0.49154(11) 0.4347(6) 0.27689(11) 0.0223(5) Uiso 1.000000 R
C15 C 0.22001(11) 0.2149(6) 0.46295(11) 0.0187(5) Uani 1.000000 .
C16 C 0.63452(12) 0.0766(6) 0.21572(11) 0.0198(5) Uani 1.000000 .
C17 C 0.08667(11) 0.1829(6) 0.46242(11) 0.0181(4) Uani 1.000000 .
C18 C 0.53860(11) 0.3310(6) 0.41191(11) 0.0179(4) Uani 1.000000 .
C19 C 0.56720(11) 0.2473(6) 0.21514(11) 0.0200(5) Uani 1.000000 .
H19 H 0.54321(11) 0.3105(6) 0.17134(11) 0.0240(6) Uiso 1.000000 R
C20 C 0.21119(12) 0.5570(6) 0.32964(11) 0.0182(5) Uani 1.000000 .
O1 O 0.02563(8) 0.2549(5) 0.42437(8) 0.0231(4) Uani 1.000000 .
H1 H -0.00836(14) 0.173(7) 0.4450(8) 0.0347(6) Uiso 1.000000 G
O2 O 0.57541(8) 0.2299(4) 0.47202(7) 0.0222(4) Uani 1.000000 .
H2 H 0.5564(9) 0.313(6) 0.50691(9) 0.0333(5) Uiso 1.000000 G
O3 O 0.48146(8) 0.5017(4) 0.41320(8) 0.0215(4) Uani 1.000000 .
O4 O 0.08781(8) 0.0270(4) 0.52135(8) 0.0222(4) Uani 1.000000 .
N11 N 0.34105(10) 0.5513(6) 0.32970(11) 0.0230(4) Uani 1.000000 .
H13 H 0.3281(13) 0.252(7) 0.4551(12) 0.022(6) Uiso 1.000000 .
H9a H 0.6425(15) 0.043(8) 0.1103(16) 0.038(8) Uiso 1.000000 .
H11a H 0.3390(13) 0.700(7) 0.2933(14) 0.023(7) Uiso 1.000000 .
H15 H 0.2212(11) 0.079(6) 0.5112(12) 0.012(5) Uiso 1.000000 .
H20 H 0.2080(12) 0.680(6) 0.2842(12) 0.019(6) Uiso 1.000000 .
H6 H 0.0992(12) 0.528(6) 0.3345(12) 0.019(6) Uiso 1.000000 .
H11b H 0.3806(15) 0.526(7) 0.3532(14) 0.028(7) Uiso 1.000000 .
H9b H 0.7000(15) -0.174(8) 0.1542(15) 0.039(8) Uiso 1.000000 .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C6 0.0164(10) 0.0191(11) 0.0168(10) 0.0006(9) -0.0007(8) -0.0019(8)
C7 0.0158(10) 0.0205(11) 0.0216(11) -0.0002(9) 0.0009(8) 0.0003(9)
C8 0.0180(10) 0.0201(11) 0.0173(10) -0.0007(9) 0.0015(8) -0.0036(8)
N9 0.0246(10) 0.0388(13) 0.0167(10) 0.0035(10) 0.0025(8) -0.0014(9)
C10 0.0169(10) 0.0156(10) 0.0152(10) -0.0013(8) 0.0021(8) -0.0023(8)
C11 0.0162(10) 0.0153(10) 0.0171(10) -0.0021(8) 0.0020(8) -0.0005(8)
C12 0.0183(10) 0.0183(10) 0.0161(10) -0.0019(9) -0.0005(8) 0.0014(8)
C13 0.0158(10) 0.0211(11) 0.0186(10) 0.0018(9) -0.0026(8) -0.0012(9)
C14 0.0142(10) 0.0208(11) 0.0206(10) -0.0004(9) -0.0000(8) -0.0008(9)
C15 0.0203(10) 0.0201(11) 0.0154(10) 0.0003(9) -0.0005(8) -0.0014(9)
C16 0.0205(11) 0.0208(11) 0.0184(10) -0.0050(9) 0.0028(8) -0.0024(9)
C17 0.0178(10) 0.0193(10) 0.0168(10) 0.0018(9) -0.0012(8) -0.0043(9)
C18 0.0164(10) 0.0207(11) 0.0163(10) -0.0029(9) -0.0006(8) -0.0003(9)
C19 0.0201(10) 0.0237(11) 0.0156(10) -0.0035(9) -0.0022(8) 0.0019(9)
C20 0.0207(11) 0.0184(10) 0.0155(10) 0.0007(9) 0.0004(8) 0.0011(8)
O1 0.0154(7) 0.0321(9) 0.0219(8) -0.0028(7) 0.0006(6) 0.0059(7)
O2 0.0213(8) 0.0311(9) 0.0142(7) 0.0063(7) 0.0007(6) -0.0014(7)
O3 0.0157(7) 0.0306(9) 0.0180(8) 0.0041(7) 0.0003(6) -0.0017(7)
O4 0.0177(7) 0.0326(9) 0.0165(7) -0.0007(7) 0.0016(6) 0.0036(7)
N11 0.0163(9) 0.0329(11) 0.0196(10) -0.0010(9) -0.0003(8) 0.0052(9)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C6 C10 1.399(3) .
C6 C20 1.383(3) .
C6 H6 1.04(2) .
C7 H7 0.9300 .
C7 C12 1.381(3) .
C7 C16 1.404(3) .
C8 C13 1.404(3) .
C8 C20 1.406(3) .
C8 N11 1.376(3) .
N9 C16 1.381(3) .
N9 H9a 0.89(3) .
N9 H9b 0.93(3) .
C10 C15 1.403(3) .
C10 C17 1.465(3) .
C11 C12 1.400(3) .
C11 C14 1.399(3) .
C11 C18 1.462(3) .
C12 H12 0.9300 .
C13 C15 1.379(3) .
C13 H13 0.95(2) .
C14 H14 0.9300 .
C14 C19 1.372(3) .
C15 H15 1.03(2) .
C16 C19 1.402(3) .
C17 O1 1.321(2) .
C17 O4 1.238(3) .
C18 O2 1.322(2) .
C18 O3 1.239(3) .
C19 H19 0.9300 .
C20 H20 0.96(2) .
O1 H1 0.8200 .
O2 H2 0.8200 .
N11 H11a 0.87(3) .
N11 H11b 0.83(3) .

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
C20 C6 C10 120.36(19) . .
H6 C6 C10 121.0(13) . .
H6 C6 C20 118.6(13) . .
C12 C7 H7 119.69(12) . .
C16 C7 H7 119.69(13) . .
C16 C7 C12 120.6(2) . .
C20 C8 C13 118.7(2) . .
N11 C8 C13 121.12(19) . .
N11 C8 C20 120.1(2) . .
H9a N9 C16 119.8(18) . .
H9b N9 C16 115.1(17) . .
H9b N9 H9a 115(3) . .
C15 C10 C6 119.05(19) . .
C17 C10 C6 121.49(18) . .
C17 C10 C15 119.43(19) . .
C14 C11 C12 118.49(19) . .
C18 C11 C12 121.60(18) . .
C18 C11 C14 119.88(19) . .
C11 C12 C7 120.66(19) . .
H12 C12 C7 119.67(12) . .
H12 C12 C11 119.67(12) . .
C15 C13 C8 120.48(19) . .
H13 C13 C8 119.6(14) . .
H13 C13 C15 119.9(14) . .
H14 C14 C11 119.47(12) . .
C19 C14 C11 121.1(2) . .
C19 C14 H14 119.47(12) . .
C13 C15 C10 120.69(19) . .
H15 C15 C10 117.6(12) . .
H15 C15 C13 121.6(12) . .
N9 C16 C7 120.5(2) . .
C19 C16 C7 118.4(2) . .
C19 C16 N9 121.1(2) . .
O1 C17 C10 114.81(18) . .
O4 C17 C10 123.19(18) . .
O4 C17 O1 121.98(19) . .
O2 C18 C11 115.05(18) . .
O3 C18 C11 123.39(19) . .
O3 C18 O2 121.54(19) . .
C16 C19 C14 120.76(19) . .
H19 C19 C14 119.62(12) . .
H19 C19 C16 119.62(12) . .
C8 C20 C6 120.7(2) . .
H20 C20 C6 119.4(14) . .
H20 C20 C8 119.9(14) . .
H1 O1 C17 109.5 . .
H2 O2 C18 109.5 . .
H11a N11 C8 119.5(16) . .
H11b N11 C8 118.0(18) . .
H11b N11 H11a 118(2) . .

_database_code_depnum_ccdc_archive 'CCDC 983121'
#######################################################################
#
#                 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_ord120
_audit_creation_date             2013-11-11
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_chemical_formula_moiety         'C7 H7 N O2'
_chemical_formula_sum            'C7 H7 N O2'
_chemical_formula_weight         137.14
_chemical_oxdiff_formula         C7N1O2H7
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
O 0.01158 0.00611 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
N 0.00653 0.00323 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_cell_length_a                   6.2436(9)
_cell_length_b                   8.4577(12)
_cell_length_c                   12.3655(17)
_cell_angle_alpha                90
_cell_angle_beta                 100.198(15)
_cell_angle_gamma                90
_cell_volume                     642.66(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    945
_cell_measurement_temperature    102.45(10)
_cell_measurement_theta_max      28.4222
_cell_measurement_theta_min      2.9270
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30476
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.4173
_exptl_crystal_F_000             288.1657
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2300
_diffrn_reflns_theta_full        25.000000
_diffrn_reflns_theta_max         28.48
_diffrn_reflns_theta_min         2.93
_diffrn_ambient_temperature      102.45(10)
_diffrn_detector_area_resol_mean 8.3367
_diffrn_measured_fraction_theta_full 1.000000
_diffrn_measured_fraction_theta_max 0.868098
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -86.00   17.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -21.2308  -19.0000   90.0000 103

#__ type_ start__ end____ width___ exp.time_
  2 omega -110.00  -45.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -21.2308  179.0000  -60.0000 65

#__ type_ start__ end____ width___ exp.time_
  3 omega   51.00   96.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       22.6371 -179.0000    0.0000 45
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0126452000
_diffrn_orient_matrix_UB_12      -0.0746690000
_diffrn_orient_matrix_UB_13      -0.0243528000
_diffrn_orient_matrix_UB_21      -0.0771595000
_diffrn_orient_matrix_UB_22      -0.0331181000
_diffrn_orient_matrix_UB_23      0.0291696000
_diffrn_orient_matrix_UB_31      -0.0846292000
_diffrn_orient_matrix_UB_32      0.0189670000
_diffrn_orient_matrix_UB_33      -0.0443429000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              6
_reflns_limit_h_min              -8
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              -5
_reflns_number_gt                1133
_reflns_number_total             1415
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution    
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         0.381351
_refine_diff_density_min         -0.355925
_refine_diff_density_rms         0.084579
_refine_ls_d_res_high            0.745117
_refine_ls_d_res_low             6.945242
_refine_ls_goodness_of_fit_ref   1.058590
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    2
_refine_ls_number_parameters     114
_refine_ls_number_reflns         1415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.069918
_refine_ls_R_factor_gt           0.056788
_refine_ls_restrained_S_all      1.058590
_refine_ls_shift/su_max          0.0006
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.168259
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_refinement_flags_posn
O1 O 0.5494(2) 0.34981(17) 0.40967(10) 0.0230(4) Uani 1.000000 .
O15 O 0.8728(2) 0.33714(17) 0.52272(11) 0.0233(4) Uani 1.000000 .
N10 N 0.2675(3) -0.0549(2) 0.79688(13) 0.0185(4) Uani 1.000000 .
C1aa C 0.6766(3) 0.1789(2) 0.68382(15) 0.0180(4) Uani 1.000000 .
C13 C 0.6793(3) 0.3041(2) 0.50258(14) 0.0166(4) Uani 1.000000 .
C16 C 0.3699(3) 0.0295(2) 0.72182(13) 0.0174(4) Uani 1.000000 .
C0aa C 0.2581(3) 0.0615(2) 0.61529(14) 0.0179(4) Uani 1.000000 .
H0aa H 0.1185(3) 0.0220(2) 0.59248(14) 0.0215(5) Uiso 1.000000 R
C12 C 0.5791(3) 0.0908(2) 0.75596(15) 0.0195(5) Uani 1.000000 .
C14 C 0.5667(3) 0.2105(2) 0.57699(14) 0.0166(4) Uani 1.000000 .
C2 C 0.3556(3) 0.1520(2) 0.54397(15) 0.0180(4) Uani 1.000000 .
H2 H 0.276(3) 0.174(2) 0.4668(15) 0.008(5) Uiso 1.000000 .
H12 H 0.656(3) 0.076(3) 0.8291(17) 0.017(5) Uiso 1.000000 .
H10a H 0.175(4) -0.122(3) 0.7658(17) 0.019(5) Uiso 1.000000 .
H10b H 0.359(4) -0.098(3) 0.8512(19) 0.022(6) Uiso 1.000000 .
H1aa H 0.814(4) 0.220(3) 0.7063(17) 0.024(5) Uiso 1.000000 .
H1 H 0.636(4) 0.419(3) 0.369(2) 0.044(7) Uiso 1.000000 .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0204(7) 0.0315(8) 0.0168(7) -0.0023(6) 0.0022(6) 0.0056(6)
O15 0.0185(7) 0.0295(8) 0.0213(7) -0.0039(6) 0.0021(6) 0.0029(5)
N10 0.0193(8) 0.0192(8) 0.0168(8) -0.0031(7) 0.0027(7) 0.0005(6)
C1aa 0.0154(9) 0.0177(9) 0.0202(10) -0.0015(8) 0.0011(8) -0.0016(7)
C13 0.0183(9) 0.0167(9) 0.0145(9) 0.0018(7) 0.0022(7) -0.0037(7)
C16 0.0220(9) 0.0152(8) 0.0159(9) 0.0017(7) 0.0057(7) -0.0020(7)
C0aa 0.0157(9) 0.0198(9) 0.0182(9) -0.0003(7) 0.0028(7) -0.0039(7)
C12 0.0210(10) 0.0213(9) 0.0146(9) 0.0022(8) -0.0009(8) 0.0004(7)
C14 0.0184(9) 0.0163(8) 0.0158(9) 0.0009(7) 0.0045(8) -0.0013(6)
C2 0.0193(9) 0.0196(9) 0.0148(9) 0.0012(7) 0.0020(7) -0.0027(7)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C13 1.341(2) .
O1 H1 0.99(3) .
O15 C13 1.222(2) .
N10 C16 1.411(2) .
N10 H10a 0.86(2) .
N10 H10b 0.88(2) .
C1aa C12 1.383(3) .
C1aa C14 1.402(3) .
C1aa H1aa 0.92(2) .
C13 C14 1.482(3) .
C16 C0aa 1.404(2) .
C16 C12 1.399(3) .
C0aa H0aa 0.9300 .
C0aa C2 1.387(3) .
C12 H12 0.95(2) .
C14 C2 1.399(3) .
C2 H2 1.013(18) .

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
H1 O1 C13 107.7(14) . .
H10a N10 C16 113.1(14) . .
H10b N10 C16 113.7(14) . .
H10b N10 H10a 111(2) . .
C14 C1aa C12 120.81(17) . .
H1aa C1aa C12 120.0(13) . .
H1aa C1aa C14 119.1(14) . .
O15 C13 O1 122.33(17) . .
C14 C13 O1 113.88(15) . .
C14 C13 O15 123.78(17) . .
C0aa C16 N10 120.46(16) . .
C12 C16 N10 119.78(16) . .
C12 C16 C0aa 119.63(17) . .
H0aa C0aa C16 119.94(11) . .
C2 C0aa C16 120.12(16) . .
C2 C0aa H0aa 119.94(10) . .
C16 C12 C1aa 119.92(17) . .
H12 C12 C1aa 118.2(13) . .
H12 C12 C16 121.8(13) . .
C13 C14 C1aa 118.69(16) . .
C2 C14 C1aa 119.08(17) . .
C2 C14 C13 122.23(16) . .
C14 C2 C0aa 120.41(16) . .
H2 C2 C0aa 120.1(11) . .
H2 C2 C14 119.4(11) . .

_database_code_depnum_ccdc_archive 'CCDC 983122'
